# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2003


data_global

_journal_coden_Cambridge         177

loop_
_publ_author_name
'Antony J. Fairbanks'
'David J. Chambers'
'Graham R. Evans'
'H.Y. Godage'

_publ_contact_author_name        'Dr Antony J Fairbanks'
_publ_contact_author_address     
;
Dyson Perrins Laboratory
Oxford University
South Parks Road
Oxford
OX1 3QY
UNITED KINGDOM
;

_publ_contact_author_email       ANTONY.FAIRBANKS@CHEM.OX.AC.UK

_publ_requested_journal          'Organic & Biomolecular Chemistry'

_publ_section_title              
;
Stereoselective synthesis of C-glycosides from
carboxylic acids: the tandem Tebbe/Claisen approach
;

data_CRYSTALS_cif_a
_database_code_CSD               212630
#=============================================================
# Diffractometer details
#=============================================================
_diffrn_measurement_device_type  
;
Nonius KappaCCD
;
_diffrn_radiation_monochromator  graphite
_computing_data_collection       
;
KappaCCD software 'Collect' (Nonius, 2000)
;
_computing_data_reduction        
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_cell_refinement       
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
#=============================================================
# General computing
#=============================================================
_computing_structure_refinement  
;
CRYSTALS (Watkin et al, 2001)
;
_computing_publication_material  
;
CRYSTALS (Watkin et al, 2001)
;
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1992)'

_chemical_name_systematic        # IUPAC name, in full
;
?
;
_chemical_melting_point          'not measured'
_refine_ls_matrix_type           full
_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_chemical_absolute_configuration syn
#=============================================================
_cell_length_a                   8.4698(2)
_cell_angle_alpha                90
_cell_length_b                   6.4952(2)
_cell_angle_beta                 94.0089(6)
_cell_length_c                   20.0695(4)
_cell_angle_gamma                90
_cell_volume                     1101.38(5)
_symmetry_cell_setting           'Monoclinic '
_symmetry_space_group_name_H-M   'P 1 21 1 '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-z
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
'C   ' 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 International_Tables_Vol_IV_Table_2.2B
'H   ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997
0.0030 International_Tables_Vol_IV_Table_2.2B
'O   ' 0.0080 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 International_Tables_Vol_IV_Table_2.2B
'Si  ' 0.0720 0.0710 6.2915 2.4386 3.0353 32.3337 1.9891 0.6785 1.5410 81.6937
1.1407 International_Tables_Vol_IV_Table_2.2B
_chemical_formula_sum            ' C22 H32 O4 Si1 '
_chemical_formula_moiety         ' C22 H32 O4 Si1 '
_chemical_compound_source        
;
synthesis as described
;
_chemical_formula_weight         388.58
_cell_measurement_reflns_used    10755
_cell_measurement_theta_min      5
_cell_measurement_theta_max      28
_cell_measurement_temperature    150
_cell_formula_units_Z            2
_exptl_crystal_description       ' plate '
_exptl_crystal_colour            ' colourless '
_exptl_crystal_size_min          0.08
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.36
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_F_000             420.248
_exptl_absorpt_coefficient_mu    0.129
_diffrn_measurement_method       ω
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  0.99
_diffrn_standards_interval_time  0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_diffrn_standards_decay_%        0.00
_diffrn_ambient_temperature      150
_diffrn_reflns_number            10755
_reflns_number_total             2712
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_measured_fraction_theta_max 0.995
_reflns_number_gt                2140
_diffrn_reflns_theta_min         5.10
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_reflns_limit_h_min              -10
_reflns_limit_h_max              10
_reflns_limit_k_min              0
_reflns_limit_k_max              8
_reflns_limit_l_min              0
_reflns_limit_l_max              26
_refine_diff_density_min         -0.14
_refine_diff_density_max         0.14
_reflns_threshold_expression     >3.00σ(I)
_refine_ls_number_reflns         2140
_refine_ls_number_parameters     245
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0373
_refine_ls_goodness_of_fit_ref   1.0489
_refine_ls_shift/su_max          0.006034
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Chebychev polynomial with 3 parameters (Carruthers & Watkin , 1979)
2.63    -1.35     1.79
;
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073

# Uequiv = arithmetic mean of Ui
# i.e. Ueqiv = (U1+U2+U3)/3

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
O1 0.0341(2) 0.2339(3) 0.30953(9) 0.0318 1.0000 Uani
C1 0.0207(3) 0.1308(4) 0.37227(12) 0.0277 1.0000 Uani
C2 0.0265(3) -0.0994(4) 0.36526(12) 0.0280 1.0000 Uani
C3 0.0582(3) -0.1930(4) 0.30877(12) 0.0285 1.0000 Uani
C4 0.1006(2) -0.0725(4) 0.24961(11) 0.0256 1.0000 Uani
C5 0.1527(3) 0.1429(4) 0.27129(12) 0.0287 1.0000 Uani
C6 0.1742(3) 0.2828(4) 0.21254(14) 0.0368 1.0000 Uani
O2 0.2790(2) 0.1942(3) 0.16808(9) 0.0389 1.0000 Uani
Si1 0.31894(7) -0.05233(13) 0.15984(3) 0.0266 1.0000 Uani
O3 0.22637(19) -0.1739(3) 0.21786(8) 0.0281 1.0000 Uani
C7 -0.1365(3) 0.1956(4) 0.39793(14) 0.0339 1.0000 Uani
C8 -0.1394(3) 0.4125(4) 0.42510(11) 0.0268 1.0000 Uani
O4 -0.0210(2) 0.4861(3) 0.45337(9) 0.0350 1.0000 Uani
C9 -0.2932(3) 0.5278(4) 0.42094(11) 0.0293 1.0000 Uani
C10 -0.4270(3) 0.4626(5) 0.38277(13) 0.0425 1.0000 Uani
C11 -0.5649(4) 0.5783(6) 0.38004(16) 0.0543 1.0000 Uani
C12 -0.5714(4) 0.7590(5) 0.41639(15) 0.0453 1.0000 Uani
C13 -0.4395(3) 0.8242(4) 0.45507(14) 0.0378 1.0000 Uani
C14 -0.3005(3) 0.7104(4) 0.45757(12) 0.0298 1.0000 Uani
C15 0.2357(3) -0.1348(4) 0.07438(12) 0.0322 1.0000 Uani
C16 0.0543(3) -0.1209(6) 0.07424(15) 0.0520 1.0000 Uani
C17 0.2885(4) 0.0081(6) 0.01945(14) 0.0529 1.0000 Uani
C18 0.2791(4) -0.3570(5) 0.05846(15) 0.0464 1.0000 Uani
C19 0.5382(3) -0.0944(5) 0.18015(13) 0.0406 1.0000 Uani
C20 0.6350(4) -0.0037(8) 0.12572(17) 0.0669 1.0000 Uani
C21 0.5760(4) -0.3234(7) 0.18993(18) 0.0630 1.0000 Uani
C22 0.5837(4) 0.0193(7) 0.24610(15) 0.0585 1.0000 Uani
H11 0.1119 0.1700 0.4041 0.0335 1.0000 Uiso
H21 0.0056 -0.1861 0.4049 0.0339 1.0000 Uiso
H31 0.0535 -0.3466 0.3061 0.0344 1.0000 Uiso
H41 0.0059 -0.0625 0.2171 0.0308 1.0000 Uiso
H51 0.2562 0.1283 0.2980 0.0348 1.0000 Uiso
H61 0.2188 0.4172 0.2293 0.0449 1.0000 Uiso
H62 0.0690 0.3066 0.1880 0.0449 1.0000 Uiso
H71 -0.1618 0.0989 0.4344 0.0411 1.0000 Uiso
H72 -0.2197 0.1845 0.3602 0.0411 1.0000 Uiso
H101 -0.4239 0.3311 0.3570 0.0504 1.0000 Uiso
H111 -0.6600 0.5311 0.3517 0.0641 1.0000 Uiso
H121 -0.6711 0.8418 0.4147 0.0541 1.0000 Uiso
H131 -0.4443 0.9544 0.4815 0.0458 1.0000 Uiso
H141 -0.2055 0.7590 0.4856 0.0360 1.0000 Uiso
H161 0.0058 -0.1637 0.0295 0.0620 1.0000 Uiso
H162 0.0164 -0.2141 0.1094 0.0620 1.0000 Uiso
H163 0.0230 0.0240 0.0837 0.0620 1.0000 Uiso
H171 0.2421 -0.0406 -0.0250 0.0634 1.0000 Uiso
H172 0.4067 0.0068 0.0197 0.0634 1.0000 Uiso
H173 0.2514 0.1514 0.0277 0.0634 1.0000 Uiso
H181 0.2327 -0.3940 0.0128 0.0555 1.0000 Uiso
H182 0.3969 -0.3710 0.0600 0.0555 1.0000 Uiso
H183 0.2362 -0.4514 0.0922 0.0555 1.0000 Uiso
H201 0.7502 -0.0278 0.1375 0.0808 1.0000 Uiso
H202 0.6145 0.1477 0.1220 0.0808 1.0000 Uiso
H203 0.6037 -0.0715 0.0821 0.0808 1.0000 Uiso
H211 0.6923 -0.3411 0.2006 0.0748 1.0000 Uiso
H212 0.5171 -0.3785 0.2276 0.0748 1.0000 Uiso
H213 0.5432 -0.4001 0.1480 0.0748 1.0000 Uiso
H221 0.6993 0.0001 0.2583 0.0699 1.0000 Uiso
H222 0.5213 -0.0379 0.2823 0.0699 1.0000 Uiso
H223 0.5601 0.1694 0.2404 0.0699 1.0000 Uiso
_refine_ls_extinction_method     None
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C1 . 1.438(3) yes
O1 . C5 . 1.433(3) yes
C1 . C2 . 1.503(3) yes
C1 . C7 . 1.520(3) yes
C1 . H11 . 1.000 no
C2 . C3 . 1.330(3) yes
C2 . H21 . 1.000 no
C3 . C4 . 1.487(3) yes
C3 . H31 . 1.000 no
C4 . C5 . 1.522(3) yes
C4 . O3 . 1.439(3) yes
C4 . H41 . 1.000 no
C5 . C6 . 1.509(4) yes
C5 . H51 . 1.000 no
C6 . O2 . 1.423(3) yes
C6 . H61 . 1.000 no
C6 . H62 . 1.000 no
O2 . Si1 . 1.648(2) yes
Si1 . O3 . 1.6499(17) yes
Si1 . C15 . 1.886(3) yes
Si1 . C19 . 1.893(3) yes
C7 . C8 . 1.511(3) yes
C7 . H71 . 1.000 no
C7 . H72 . 1.000 no
C8 . O4 . 1.215(3) yes
C8 . C9 . 1.499(3) yes
C9 . C10 . 1.389(4) yes
C9 . C14 . 1.399(3) yes
C10 . C11 . 1.387(4) yes
C10 . H101 . 1.000 no
C11 . C12 . 1.385(5) yes
C11 . H111 . 1.000 no
C12 . C13 . 1.381(4) yes
C12 . H121 . 1.000 no
C13 . C14 . 1.388(4) yes
C13 . H131 . 1.000 no
C14 . H141 . 1.000 no
C15 . C16 . 1.539(4) yes
C15 . C17 . 1.532(4) yes
C15 . C18 . 1.529(4) yes
C16 . H161 . 1.000 no
C16 . H162 . 1.000 no
C16 . H163 . 1.000 no
C17 . H171 . 1.000 no
C17 . H172 . 1.000 no
C17 . H173 . 1.000 no
C18 . H181 . 1.000 no
C18 . H182 . 1.000 no
C18 . H183 . 1.000 no
C19 . C20 . 1.530(4) yes
C19 . C21 . 1.531(5) yes
C19 . C22 . 1.541(4) yes
C20 . H201 . 1.000 no
C20 . H202 . 1.000 no
C20 . H203 . 1.000 no
C21 . H211 . 1.000 no
C21 . H212 . 1.000 no
C21 . H213 . 1.000 no
C22 . H221 . 1.000 no
C22 . H222 . 1.000 no
C22 . H223 . 1.000 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 . O1 . C5 . 112.24(18) yes
O1 . C1 . C2 . 112.10(19) yes
O1 . C1 . C7 . 107.0(2) yes
C2 . C1 . C7 . 110.1(2) yes
O1 . C1 . H11 . 109.6 no
C2 . C1 . H11 . 106.5 no
C7 . C1 . H11 . 111.6 no
C1 . C2 . C3 . 123.0(2) yes
C1 . C2 . H21 . 118.5 no
C3 . C2 . H21 . 118.5 no
C2 . C3 . C4 . 121.0(2) yes
C2 . C3 . H31 . 119.5 no
C4 . C3 . H31 . 119.5 no
C3 . C4 . C5 . 109.68(19) yes
C3 . C4 . O3 . 109.91(19) yes
C5 . C4 . O3 . 109.79(18) yes
C3 . C4 . H41 . 109.1 no
C5 . C4 . H41 . 109.3 no
O3 . C4 . H41 . 109.04 no
O1 . C5 . C4 . 109.40(18) yes
O1 . C5 . C6 . 107.32(19) yes
C4 . C5 . C6 . 112.2(2) yes
O1 . C5 . H51 . 111.9 no
C4 . C5 . H51 . 107.0 no
C6 . C5 . H51 . 109.1 no
C5 . C6 . O2 . 111.2(2) yes
C5 . C6 . H61 . 109.0 no
O2 . C6 . H61 . 109.0 no
C5 . C6 . H62 . 109.0 no
O2 . C6 . H62 . 109.0 no
H61 . C6 . H62 . 109.5 no
C6 . O2 . Si1 . 126.67(16) yes
O2 . Si1 . O3 . 106.46(9) yes
O2 . Si1 . C15 . 107.52(12) yes
O3 . Si1 . C15 . 109.88(11) yes
O2 . Si1 . C19 . 108.91(13) yes
O3 . Si1 . C19 . 106.63(11) yes
C15 . Si1 . C19 . 116.98(12) yes
C4 . O3 . Si1 . 119.79(14) yes
C1 . C7 . C8 . 114.7(2) yes
C1 . C7 . H71 . 108.2 no
C8 . C7 . H71 . 108.2 no
C1 . C7 . H72 . 108.2 no
C8 . C7 . H72 . 108.2 no
H71 . C7 . H72 . 109.5 no
C7 . C8 . O4 . 120.1(2) yes
C7 . C8 . C9 . 118.8(2) yes
O4 . C8 . C9 . 121.0(2) yes
C8 . C9 . C10 . 123.4(2) yes
C8 . C9 . C14 . 117.7(2) yes
C10 . C9 . C14 . 118.9(2) yes
C9 . C10 . C11 . 120.6(3) yes
C9 . C10 . H101 . 119.7 no
C11 . C10 . H101 . 119.7 no
C10 . C11 . C12 . 120.2(3) yes
C10 . C11 . H111 . 119.9 no
C12 . C11 . H111 . 119.9 no
C11 . C12 . C13 . 119.7(3) yes
C11 . C12 . H121 . 120.1 no
C13 . C12 . H121 . 120.1 no
C12 . C13 . C14 . 120.5(3) yes
C12 . C13 . H131 . 119.7 no
C14 . C13 . H131 . 119.7 no
C9 . C14 . C13 . 120.1(2) yes
C9 . C14 . H141 . 120.0 no
C13 . C14 . H141 . 120.0 no
Si1 . C15 . C16 . 107.15(18) yes
Si1 . C15 . C17 . 111.9(2) yes
C16 . C15 . C17 . 107.8(3) yes
Si1 . C15 . C18 . 112.21(19) yes
C16 . C15 . C18 . 108.0(3) yes
C17 . C15 . C18 . 109.6(2) yes
C15 . C16 . H161 . 109.5 no
C15 . C16 . H162 . 109.5 no
H161 . C16 . H162 . 109.5 no
C15 . C16 . H163 . 109.5 no
H161 . C16 . H163 . 109.5 no
H162 . C16 . H163 . 109.5 no
C15 . C17 . H171 . 109.5 no
C15 . C17 . H172 . 109.5 no
H171 . C17 . H172 . 109.5 no
C15 . C17 . H173 . 109.5 no
H171 . C17 . H173 . 109.5 no
H172 . C17 . H173 . 109.5 no
C15 . C18 . H181 . 109.5 no
C15 . C18 . H182 . 109.5 no
H181 . C18 . H182 . 109.5 no
C15 . C18 . H183 . 109.5 no
H181 . C18 . H183 . 109.5 no
H182 . C18 . H183 . 109.5 no
Si1 . C19 . C20 . 111.0(2) yes
Si1 . C19 . C21 . 111.2(2) yes
C20 . C19 . C21 . 110.4(3) yes
Si1 . C19 . C22 . 107.38(19) yes
C20 . C19 . C22 . 108.3(3) yes
C21 . C19 . C22 . 108.5(3) yes
C19 . C20 . H201 . 109.5 no
C19 . C20 . H202 . 109.5 no
H201 . C20 . H202 . 109.5 no
C19 . C20 . H203 . 109.5 no
H201 . C20 . H203 . 109.5 no
H202 . C20 . H203 . 109.5 no
C19 . C21 . H211 . 109.5 no
C19 . C21 . H212 . 109.5 no
H211 . C21 . H212 . 109.5 no
C19 . C21 . H213 . 109.5 no
H211 . C21 . H213 . 109.5 no
H212 . C21 . H213 . 109.5 no
C19 . C22 . H221 . 109.5 no
C19 . C22 . H222 . 109.5 no
H221 . C22 . H222 . 109.5 no
C19 . C22 . H223 . 109.5 no
H221 . C22 . H223 . 109.5 no
H222 . C22 . H223 . 109.5 no

data_CRYSTALS_cif_b
_database_code_CSD               212631
#==========================================================================
# Diffractometer details
#==========================================================================
_diffrn_measurement_device_type  
;
Nonius KappaCCD
;
_diffrn_radiation_monochromator  graphite
_computing_data_collection       
;
KappaCCD software 'Collect' (Nonius, 2000)
;
_computing_data_reduction        
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_cell_refinement       
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
#==========================================================================
# General computing
#==========================================================================
_computing_structure_refinement  
;
CRYSTALS (Watkin et al, 2001)
;
_computing_publication_material  
;
CRYSTALS (Watkin et al, 2001)
;
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1992)'

_chemical_name_systematic        # IUPAC name, in full
;
?
;
_chemical_melting_point          'not measured'
_refine_ls_matrix_type           full
_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_chemical_absolute_configuration syn
#=============================================================
_cell_length_a                   5.8009(2)
_cell_angle_alpha                90
_cell_length_b                   13.1214(4)
_cell_angle_beta                 90
_cell_length_c                   18.5666(5)
_cell_angle_gamma                90
_cell_volume                     1413.2
_symmetry_cell_setting           'Orthorhombic '
_symmetry_space_group_name_H-M   'P 21 21 21 '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
'C   ' 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 International_Tables_Vol_IV_Table_2.2B
'H   ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997
0.0030 International_Tables_Vol_IV_Table_2.2B
'O   ' 0.0080 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 International_Tables_Vol_IV_Table_2.2B
_chemical_formula_sum            ' C16 H18 O4 '
_chemical_formula_moiety         ' C16 H18 O4 '
_chemical_compound_source        
;
synthesis as derscribed
;
_chemical_formula_weight         274.32
_cell_measurement_reflns_used    8918
_cell_measurement_theta_min      5
_cell_measurement_theta_max      28
_cell_measurement_temperature    150
_cell_formula_units_Z            4
_exptl_crystal_description       ' fragment '
_exptl_crystal_colour            ' colourless '
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_max          0.40
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_F_000             584.192
_exptl_absorpt_coefficient_mu    0.092
_diffrn_measurement_method       ω
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_T_max  0.99
_diffrn_standards_interval_time  0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_diffrn_standards_decay_%        0.00
_diffrn_ambient_temperature      150
_diffrn_reflns_number            8918
_reflns_number_total             1868
# 1887 including systematic absences
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_measured_fraction_theta_max 0.994
_reflns_number_gt                1552
_diffrn_reflns_theta_min         5.18
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_reflns_limit_h_min              0
_reflns_limit_h_max              7
_reflns_limit_k_min              0
_reflns_limit_k_max              17
_reflns_limit_l_min              0
_reflns_limit_l_max              24
_refine_diff_density_min         -0.14
_refine_diff_density_max         0.16
_reflns_threshold_expression     >3.00σ(I)
_refine_ls_number_reflns         1552
_refine_ls_number_parameters     181
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0319
_refine_ls_goodness_of_fit_ref   1.0546
_refine_ls_shift/su_max          0.000275
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Chebychev polynomial with 3 parameters (Carruthers & Watkin , 1979)
0.414    0.130    0.146
;
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073

# Uequiv = arithmetic mean of Ui
# i.e. Ueqiv = (U1+U2+U3)/3

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
O1 0.1089(2) 0.56034(8) 0.21285(7) 0.0316 1.0000 Uani
C1 -0.0830(3) 0.55814(13) 0.25579(9) 0.0289 1.0000 Uani
C2 -0.1936(3) 0.47493(13) 0.27673(9) 0.0265 1.0000 Uani
C3 -0.1239(3) 0.36966(12) 0.25271(8) 0.0227 1.0000 Uani
C4 0.0297(3) 0.38268(11) 0.18710(8) 0.0202 1.0000 Uani
C5 0.2134(3) 0.46244(12) 0.20167(8) 0.0228 1.0000 Uani
C6 0.3719(3) 0.47161(12) 0.13731(9) 0.0270 1.0000 Uani
O2 0.0103(2) 0.31739(9) 0.30687(6) 0.0256 1.0000 Uani
C7 -0.1081(3) 0.27515(13) 0.36357(9) 0.0277 1.0000 Uani
C8 -0.3347(4) 0.27511(16) 0.37274(11) 0.0366 1.0000 Uani
C9 0.0595(4) 0.22681(16) 0.4137(1) 0.0395 1.0000 Uani
O3 0.1394(2) 0.28900(8) 0.16784(6) 0.0209 1.0000 Uani
O4 0.4618(2) 0.37206(8) 0.12054(6) 0.0252 1.0000 Uani
C10 0.2811(3) 0.30267(12) 0.10573(8) 0.0219 1.0000 Uani
C11 0.3814(3) 0.20055(12) 0.08589(8) 0.0216 1.0000 Uani
C12 0.5910(3) 0.16712(13) 0.11327(9) 0.0280 1.0000 Uani
C13 0.6738(3) 0.07085(13) 0.0952(1) 0.0301 1.0000 Uani
C14 0.5478(3) 0.00860(13) 0.05014(9) 0.0290 1.0000 Uani
C15 0.3392(3) 0.04161(13) 0.02232(9) 0.0313 1.0000 Uani
C16 0.2571(3) 0.13784(13) 0.03987(8) 0.0269 1.0000 Uani
H11 -0.1449 0.6251 0.2728 0.0347 1.0000 Uiso
H21 -0.3287 0.4823 0.3098 0.0319 1.0000 Uiso
H31 -0.2662 0.3289 0.2429 0.0272 1.0000 Uiso
H41 -0.0706 0.4051 0.1463 0.0243 1.0000 Uiso
H51 0.3013 0.4410 0.2455 0.0273 1.0000 Uiso
H61 0.5019 0.5189 0.1489 0.0324 1.0000 Uiso
H62 0.2840 0.4987 0.0951 0.0324 1.0000 Uiso
H81 -0.4036 0.2420 0.4162 0.0439 1.0000 Uiso
H82 -0.4368 0.3082 0.3362 0.0439 1.0000 Uiso
H91 -0.0255 0.1959 0.4552 0.0475 1.0000 Uiso
H92 0.1692 0.2796 0.4320 0.0475 1.0000 Uiso
H93 0.1472 0.1725 0.3877 0.0475 1.0000 Uiso
H101 0.1869 0.3308 0.0652 0.0263 1.0000 Uiso
H121 0.6824 0.2122 0.1460 0.0336 1.0000 Uiso
H131 0.8247 0.0468 0.1150 0.0362 1.0000 Uiso
H141 0.6073 -0.0607 0.0375 0.0348 1.0000 Uiso
H151 0.2480 -0.0037 -0.0103 0.0375 1.0000 Uiso
H161 0.1076 0.1621 0.0192 0.0323 1.0000 Uiso
_refine_ls_extinction_method     None
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C1 . 1.369(2) yes
O1 . C5 . 1.4355(19) yes
C1 . C2 . 1.325(3) yes
C1 . H11 . 1.0000 no
C2 . C3 . 1.507(2) yes
C2 . H21 . 1.0000 no
C3 . C4 . 1.519(2) yes
C3 . O2 . 1.4448(19) yes
C3 . H31 . 1.0000 no
C4 . C5 . 1.518(2) yes
C4 . O3 . 1.4295(17) yes
C4 . H41 . 1.0000 no
C5 . C6 . 1.513(2) yes
C5 . H51 . 1.0000 no
C6 . O4 . 1.440(2) yes
C6 . H61 . 1.0000 no
C6 . H62 . 1.0000 no
O2 . C7 . 1.3737(19) yes
C7 . C8 . 1.326(3) yes
C7 . C9 . 1.488(3) yes
C8 . H81 . 1.0000 no
C8 . H82 . 1.000 no
C9 . H91 . 1.0000 no
C9 . H92 . 1.000 no
C9 . H93 . 1.000 no
O3 . C10 . 1.4277(18) yes
O4 . C10 . 1.4153(19) yes
C10 . C11 . 1.506(2) yes
C10 . H101 . 1.0000 no
C11 . C12 . 1.389(2) yes
C11 . C16 . 1.388(2) yes
C12 . C13 . 1.392(2) yes
C12 . H121 . 1.0000 no
C13 . C14 . 1.380(3) yes
C13 . H131 . 1.0000 no
C14 . C15 . 1.385(3) yes
C14 . H141 . 1.0000 no
C15 . C16 . 1.388(2) yes
C15 . H151 . 1.0000 no
C16 . H161 . 1.0000 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 . O1 . C5 . 114.12(12) yes
O1 . C1 . C2 . 125.58(15) yes
O1 . C1 . H11 . 117.21 no
C2 . C1 . H11 . 117.21 no
C1 . C2 . C3 . 122.60(16) yes
C1 . C2 . H21 . 118.70 no
C3 . C2 . H21 . 118.70 no
C2 . C3 . C4 . 106.95(13) yes
C2 . C3 . O2 . 111.95(13) yes
C4 . C3 . O2 . 107.19(13) yes
C2 . C3 . H31 . 108.80 no
C4 . C3 . H31 . 113.43 no
O2 . C3 . H31 . 108.57 no
C3 . C4 . C5 . 110.27(12) yes
C3 . C4 . O3 . 111.40(12) yes
C5 . C4 . O3 . 108.97(13) yes
C3 . C4 . H41 . 107.45 no
C5 . C4 . H41 . 109.94 no
O3 . C4 . H41 . 108.78 no
O1 . C5 . C4 . 110.26(13) yes
O1 . C5 . C6 . 107.45(13) yes
C4 . C5 . C6 . 109.93(13) yes
O1 . C5 . H51 . 110.45 no
C4 . C5 . H51 . 107.99 no
C6 . C5 . H51 . 110.78 no
C5 . C6 . O4 . 108.58(12) yes
C5 . C6 . H61 . 109.69 no
O4 . C6 . H61 . 109.69 no
C5 . C6 . H62 . 109.69 no
O4 . C6 . H62 . 109.69 no
H61 . C6 . H62 . 109.47 no
C3 . O2 . C7 . 117.10(13) yes
O2 . C7 . C8 . 126.46(18) yes
O2 . C7 . C9 . 108.98(16) yes
C8 . C7 . C9 . 124.55(18) yes
C7 . C8 . H81 . 120.0 no
C7 . C8 . H82 . 120.00 no
H81 . C8 . H82 . 120.0 no
C7 . C9 . H91 . 109.47 no
C7 . C9 . H92 . 109.47 no
H91 . C9 . H92 . 109.48 no
C7 . C9 . H93 . 109.47 no
H91 . C9 . H93 . 109.48 no
H92 . C9 . H93 . 109.5 no
C4 . O3 . C10 . 110.51(11) yes
C6 . O4 . C10 . 110.95(13) yes
O3 . C10 . O4 . 110.51(12) yes
O3 . C10 . C11 . 107.95(12) yes
O4 . C10 . C11 . 109.50(13) yes
O3 . C10 . H101 . 109.81 no
O4 . C10 . H101 . 108.27 no
C11 . C10 . H101 . 110.81 no
C10 . C11 . C12 . 121.96(14) yes
C10 . C11 . C16 . 118.50(15) yes
C12 . C11 . C16 . 119.52(15) yes
C11 . C12 . C13 . 120.05(16) yes
C11 . C12 . H121 . 119.98 no
C13 . C12 . H121 . 119.98 no
C12 . C13 . C14 . 120.01(17) yes
C12 . C13 . H131 . 119.99 no
C14 . C13 . H131 . 120.00 no
C13 . C14 . C15 . 120.27(16) yes
C13 . C14 . H141 . 119.86 no
C15 . C14 . H141 . 119.86 no
C14 . C15 . C16 . 119.77(16) yes
C14 . C15 . H151 . 120.11 no
C16 . C15 . H151 . 120.11 no
C11 . C16 . C15 . 120.36(16) yes
C11 . C16 . H161 . 119.82 no
C15 . C16 . H161 . 119.82 no

data_CRYSTALS_cif_c
_database_code_CSD               212632
#==========================================================================
# Diffractometer details
#==========================================================================
_diffrn_measurement_device_type  
;
Nonius KappaCCD
;
_diffrn_radiation_monochromator  graphite
_computing_data_collection       
;
KappaCCD software 'Collect' (Nonius, 2000)
;
_computing_data_reduction        
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_cell_refinement       
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
#==========================================================================
# General computing
#==========================================================================
_computing_structure_refinement  
;
CRYSTALS (Watkin et al, 2001)
;
_computing_publication_material  
;
CRYSTALS (Watkin et al, 2001)
;
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1992)'

_chemical_name_systematic        # IUPAC name, in full
;
?
;
_chemical_melting_point          'not measured'
_refine_ls_matrix_type           full
_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_chemical_absolute_structure     syn
#=============================================================
_cell_length_a                   5.1126(5)
_cell_angle_alpha                90
_cell_length_b                   14.2991(2)
_cell_angle_beta                 90
_cell_length_c                   19.1347(8)
_cell_angle_gamma                90
_cell_volume                     1398.9
_symmetry_cell_setting           'Orthorhombic '
_symmetry_space_group_name_H-M   'P 21 21 21 '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
'C   ' 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 International_Tables_Vol_IV_Table_2.2B
'H   ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997
0.0030 International_Tables_Vol_IV_Table_2.2B
'O   ' 0.0080 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 International_Tables_Vol_IV_Table_2.2B
_chemical_formula_sum            ' C16 H18 O4 '
_chemical_formula_moiety         ' C16 H18 O4 '
_chemical_compound_source        
;
synthesis as described
;
_chemical_formula_weight         274.32
_cell_measurement_reflns_used    14624
_cell_measurement_theta_min      5
_cell_measurement_theta_max      28
_cell_measurement_temperature    150
_cell_formula_units_Z            4
_exptl_crystal_description       ' prism '
_exptl_crystal_colour            ' colourless '
_exptl_crystal_size_min          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_max          0.30
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_F_000             584.192
_exptl_absorpt_coefficient_mu    0.093
_diffrn_measurement_method       ω
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_T_max  0.99
_diffrn_standards_interval_time  0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_diffrn_standards_decay_%        0.00
_diffrn_ambient_temperature      150
_diffrn_reflns_number            14624
_reflns_number_total             1864
# 1883 reflections including systematic absences
_diffrn_reflns_av_R_equivalents  0.051
_diffrn_measured_fraction_theta_max 0.995
_reflns_number_gt                1409
_diffrn_reflns_theta_min         5.11
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_reflns_limit_h_min              0
_reflns_limit_h_max              6
_reflns_limit_k_min              0
_reflns_limit_k_max              18
_reflns_limit_l_min              0
_reflns_limit_l_max              24
_refine_diff_density_min         -0.12
_refine_diff_density_max         0.16
_reflns_threshold_expression     >3.00σ(I)
_refine_ls_number_reflns         1409
_refine_ls_number_parameters     181
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_ref         0.0355
_refine_ls_goodness_of_fit_ref   1.0410
_refine_ls_shift/su_max          0.006251
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Chebychev polynomial with 3 parameters (Carruthers & Watkin , 1979)
1.93    -.283     1.35
;
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073

# Uequiv = arithmetic mean of Ui
# i.e. Ueqiv = (U1+U2+U3)/3

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
O1 0.5687(3) 0.49206(8) 0.50672(7) 0.0339 1.0000 Uani
O2 0.4229(3) 0.63930(9) 0.65736(7) 0.0314 1.0000 Uani
O3 0.1682(3) 0.68820(9) 0.56237(6) 0.0340 1.0000 Uani
O4 0.6036(3) 0.31054(11) 0.40798(8) 0.0446 1.0000 Uani
C1 0.6563(5) 0.40683(13) 0.5392(1) 0.0348 1.0000 Uani
C2 0.7283(5) 0.42047(15) 0.61479(11) 0.0403 1.0000 Uani
C3 0.6958(4) 0.50038(15) 0.6489(1) 0.0373 1.0000 Uani
C4 0.5828(4) 0.58271(13) 0.61198(9) 0.0292 1.0000 Uani
C5 0.4136(4) 0.54760(12) 0.55242(9) 0.0291 1.0000 Uani
C6 0.3041(5) 0.62998(13) 0.51296(9) 0.0363 1.0000 Uani
C7 0.8835(4) 0.37254(14) 0.49530(12) 0.0395 1.0000 Uani
C8 0.8080(4) 0.35067(13) 0.42082(11) 0.0354 1.0000 Uani
C9 0.9959(5) 0.37810(16) 0.36458(13) 0.0493 1.0000 Uani
C10 0.3345(4) 0.71712(13) 0.61857(9) 0.0298 1.0000 Uani
C11 0.1717(4) 0.78227(13) 0.66245(9) 0.0293 1.0000 Uani
C12 0.0125(5) 0.75114(15) 0.71608(11) 0.0394 1.0000 Uani
C13 -0.1532(5) 0.81368(16) 0.7502(1) 0.0439 1.0000 Uani
C14 -0.1593(5) 0.90688(15) 0.7304(1) 0.0391 1.0000 Uani
C15 0.0003(5) 0.93788(14) 0.67716(11) 0.0373 1.0000 Uani
C16 0.1663(4) 0.87603(13) 0.6434(1) 0.0331 1.0000 Uani
H11 0.5132 0.3592 0.5406 0.0418 1.0000 Uiso
H21 0.8048 0.3663 0.6407 0.0484 1.0000 Uiso
H31 0.7470 0.5053 0.6992 0.0448 1.0000 Uiso
H41 0.7308 0.6223 0.5948 0.0351 1.0000 Uiso
H51 0.2666 0.5090 0.5713 0.0349 1.0000 Uiso
H61 0.4494 0.6660 0.4906 0.0436 1.0000 Uiso
H62 0.1801 0.6078 0.4761 0.0436 1.0000 Uiso
H71 1.0215 0.4221 0.4948 0.0474 1.0000 Uiso
H72 0.9552 0.3145 0.5172 0.0474 1.0000 Uiso
H91 0.9231 0.3598 0.3180 0.0591 1.0000 Uiso
H92 1.0237 0.4473 0.3659 0.0591 1.0000 Uiso
H93 1.1666 0.3455 0.3722 0.0591 1.0000 Uiso
H101 0.4959 0.7491 0.6012 0.0358 1.0000 Uiso
H121 0.0163 0.6839 0.7303 0.0473 1.0000 Uiso
H131 -0.2679 0.7912 0.7891 0.0527 1.0000 Uiso
H141 -0.2792 0.9516 0.7547 0.0469 1.0000 Uiso
H151 -0.0037 1.0051 0.6629 0.0447 1.0000 Uiso
H161 0.2830 0.8990 0.6052 0.0397 1.0000 Uiso
_refine_ls_extinction_method     None
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C1 . 1.439(2) yes
O1 . C5 . 1.423(2) yes
O2 . C4 . 1.441(2) yes
O2 . C10 . 1.412(2) yes
O3 . C6 . 1.439(2) yes
O3 . C10 . 1.432(2) yes
O4 . C8 . 1.218(3) yes
C1 . C2 . 1.505(3) yes
C1 . C7 . 1.515(3) yes
C1 . H11 . 1.000 no
C2 . C3 . 1.326(3) yes
C2 . H21 . 1.000 no
C3 . C4 . 1.489(3) yes
C3 . H31 . 1.0000 no
C4 . C5 . 1.516(2) yes
C4 . H41 . 1.0000 no
C5 . C6 . 1.507(2) yes
C5 . H51 . 1.0000 no
C6 . H61 . 1.000 no
C6 . H62 . 1.000 no
C7 . C8 . 1.509(3) yes
C7 . H71 . 1.000 no
C7 . H72 . 1.000 no
C8 . C9 . 1.495(3) yes
C9 . H91 . 1.000 no
C9 . H92 . 1.000 no
C9 . H93 . 1.000 no
C10 . C11 . 1.505(3) yes
C10 . H101 . 1.0000 no
C11 . C12 . 1.383(3) yes
C11 . C16 . 1.389(3) yes
C12 . C13 . 1.395(3) yes
C12 . H121 . 1.000 no
C13 . C14 . 1.386(3) yes
C13 . H131 . 1.000 no
C14 . C15 . 1.379(3) yes
C14 . H141 . 1.000 no
C15 . C16 . 1.385(3) yes
C15 . H151 . 1.000 no
C16 . H161 . 1.000 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 . O1 . C5 . 112.35(14) yes
C4 . O2 . C10 . 107.90(13) yes
C6 . O3 . C10 . 111.96(16) yes
O1 . C1 . C2 . 112.43(16) yes
O1 . C1 . C7 . 105.83(16) yes
C2 . C1 . C7 . 112.79(18) yes
O1 . C1 . H11 . 111.17 no
C2 . C1 . H11 . 103.97 no
C7 . C1 . H11 . 110.79 no
C1 . C2 . C3 . 123.59(18) yes
C1 . C2 . H21 . 118.2 no
C3 . C2 . H21 . 118.2 no
C2 . C3 . C4 . 119.81(17) yes
C2 . C3 . H31 . 120.1 no
C4 . C3 . H31 . 120.1 no
O2 . C4 . C3 . 112.24(15) yes
O2 . C4 . C5 . 108.38(15) yes
C3 . C4 . C5 . 108.39(16) yes
O2 . C4 . H41 . 108.00 no
C3 . C4 . H41 . 107.99 no
C5 . C4 . H41 . 111.87 no
O1 . C5 . C4 . 109.20(15) yes
O1 . C5 . C6 . 109.60(14) yes
C4 . C5 . C6 . 109.25(15) yes
O1 . C5 . H51 . 109.49 no
C4 . C5 . H51 . 109.85 no
C6 . C5 . H51 . 109.44 no
O3 . C6 . C5 . 107.61(15) yes
O3 . C6 . H61 . 109.94 no
C5 . C6 . H61 . 109.94 no
O3 . C6 . H62 . 109.94 no
C5 . C6 . H62 . 109.94 no
H61 . C6 . H62 . 109.47 no
C1 . C7 . C8 . 113.26(17) yes
C1 . C7 . H71 . 108.52 no
C8 . C7 . H71 . 108.52 no
C1 . C7 . H72 . 108.52 no
C8 . C7 . H72 . 108.52 no
H71 . C7 . H72 . 109.47 no
O4 . C8 . C7 . 120.5(2) yes
O4 . C8 . C9 . 122.0(2) yes
C7 . C8 . C9 . 117.47(19) yes
C8 . C9 . H91 . 109.5 no
C8 . C9 . H92 . 109.5 no
H91 . C9 . H92 . 109.5 no
C8 . C9 . H93 . 109.5 no
H91 . C9 . H93 . 109.5 no
H92 . C9 . H93 . 109.5 no
O2 . C10 . O3 . 110.93(14) yes
O2 . C10 . C11 . 111.82(15) yes
O3 . C10 . C11 . 105.63(16) yes
O2 . C10 . H101 . 105.70 no
O3 . C10 . H101 . 111.89 no
C11 . C10 . H101 . 111.00 no
C10 . C11 . C12 . 122.68(17) yes
C10 . C11 . C16 . 117.54(17) yes
C12 . C11 . C16 . 119.53(18) yes
C11 . C12 . C13 . 119.92(19) yes
C11 . C12 . H121 . 120.0 no
C13 . C12 . H121 . 120.0 no
C12 . C13 . C14 . 120.1(2) yes
C12 . C13 . H131 . 119.9 no
C14 . C13 . H131 . 119.9 no
C13 . C14 . C15 . 119.9(2) yes
C13 . C14 . H141 . 120.1 no
C15 . C14 . H141 . 120.1 no
C14 . C15 . C16 . 120.10(18) yes
C14 . C15 . H151 . 119.9 no
C16 . C15 . H151 . 119.9 no
C11 . C16 . C15 . 120.43(19) yes
C11 . C16 . H161 . 119.79 no
C15 . C16 . H161 . 119.78 no



