
# ol9908880.cif

data_shelxl 
 
_audit_creation_method            SHELXL 
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_formula_moiety          ?
_chemical_formula_structural      ?
_chemical_formula_analytical      ?
_chemical_formula_sum             'C24 H21 N3 O6'
_chemical_formula_weight          447.44
_chemical_melting_point           ?
_chemical_compound_source         ?

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0181   0.0091
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0492   0.0322
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0311   0.0180
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting            P 21/n
_symmetry_space_group_name_H-M

loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                    7.439(2)
_cell_length_b                    13.539(8)
_cell_length_c                    21.216(10)
_cell_angle_alpha                 90.00
_cell_angle_beta                  91.795(15)
_cell_angle_gamma                 90.00
_cell_volume                      2135.8(16)
_cell_formula_units_Z             4
_cell_measurement_temperature     295(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?

_exptl_crystal_description        ?
_exptl_crystal_colour             ?
_exptl_crystal_size_max           0.40
_exptl_crystal_size_mid           0.15
_exptl_crystal_size_min           0.10
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.391
_exptl_crystal_density_method     ?
_exptl_crystal_F_000              936
_exptl_absorpt_coefficient_mu     0.845
_exptl_absorpt_correction_type    ?
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?

_exptl_special_details
;
 ?
;

_diffrn_ambient_temperature       295(2)
_diffrn_radiation_wavelength      1.54060
_diffrn_radiation_type            ?
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device        ?
_diffrn_measurement_method        ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             8037
_diffrn_reflns_av_R_equivalents   0.0957
_diffrn_reflns_av_sigmaI/netI     0.0520
_diffrn_reflns_limit_h_min        -5
_diffrn_reflns_limit_h_max        5
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -15
_diffrn_reflns_limit_l_max        20
_diffrn_reflns_theta_min          3.87
_diffrn_reflns_theta_max          47.90
_reflns_number_total              1655
_reflns_number_observed           1557
_reflns_observed_criterion        >2sigma(I)

_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)'
_computing_molecular_graphics     ?
_computing_publication_material   ?

_refine_special_details
;
 Refinement on F² for ALL reflections except for 0 with very negative F²
 or flagged by the user for potential systematic errors.  Weighted R-factors
 wR and all goodnesses of fit S are based on F², conventional R-factors R
 are based on F, with F set to zero for negative F². The observed
criterion
 of F² > 2sigma(F²) is used only for calculating _R_factor_obs etc. and
is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme
 'calc w=1/[\s^2^(Fo^2^)+(0.1192P)^2^+1.1282P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     ?
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        0.0326(32)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          1655
_refine_ls_number_parameters      303
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0805
_refine_ls_R_factor_obs           0.0666
_refine_ls_wR_factor_all          0.1908
_refine_ls_wR_factor_obs          0.1766
_refine_ls_goodness_of_fit_all    1.223
_refine_ls_goodness_of_fit_obs    1.174
_refine_ls_restrained_S_all       1.223
_refine_ls_restrained_S_obs       1.174
_refine_ls_shift/esd_max          -0.004
_refine_ls_shift/esd_mean         0.001

loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_thermal_displace_type
 _atom_site_occupancy
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_group
O1 O 0.2816(5) 0.1748(3) 0.65167(15) 0.0696(12) Uani 1 d . .
O2 O 0.3827(6) 0.0226(3) 0.6387(2) 0.0881(14) Uani 1 d . .
O3 O 0.7984(5) 0.1593(3) 0.7832(2) 0.0781(13) Uani 1 d . .
O4 O 0.3532(6) 0.3814(2) 0.74258(15) 0.0629(12) Uani 1 d . .
O5 O 0.7496(5) 0.2967(2) 0.63826(13) 0.0486(11) Uani 1 d . .
O6 O 0.1465(6) 0.3066(3) 0.4377(2) 0.0844(14) Uani 1 d . .
N1 N 0.5438(8) 0.2526(3) 0.7627(2) 0.0517(13) Uani 1 d . .
N2 N 0.2350(5) 0.1940(3) 0.5129(2) 0.0542(13) Uani 1 d . .
H2 H 0.2629(5) 0.1903(3) 0.5525(2) 0.065 Uiso 1 calc R .
N3 N 0.2573(6) 0.0260(3) 0.5177(2) 0.0623(14) Uani 1 d . .
C1 C 0.3523(8) 0.1010(4) 0.6734(2) 0.058(2) Uani 1 d . .
C2 C 0.4089(8) 0.0872(4) 0.7405(2) 0.071(2) Uani 1 d . .
H2A H 0.5291(8) 0.0594(4) 0.7420(2) 0.085 Uiso 1 calc R .
H2B H 0.3294(8) 0.0392(4) 0.7590(2) 0.085 Uiso 1 calc R .
C3 C 0.4097(8) 0.1794(4) 0.7810(2) 0.067(2) Uani 1 d . .
H3A H 0.2914(8) 0.2094(4) 0.7783(2) 0.080 Uiso 1 calc R .
H3B H 0.4336(8) 0.1606(4) 0.8246(2) 0.080 Uiso 1 calc R .
C4 C 0.7244(11) 0.2371(3) 0.7656(2) 0.056(2) Uani 1 d . .
C5 C 0.8249(7) 0.3269(3) 0.7421(2) 0.0498(14) Uani 1 d . .
H5 H 0.9101(7) 0.3551(3) 0.7733(2) 0.060 Uiso 1 calc R .
C6 C 0.6721(7) 0.3977(3) 0.7218(2) 0.0446(14) Uani 1 d . .
H6 H 0.6874(7) 0.4637(3) 0.7400(2) 0.054 Uiso 1 calc R .
C7 C 0.5060(10) 0.3483(3) 0.7424(2) 0.050(2) Uani 1 d . .
C8 C 0.9092(7) 0.3029(3) 0.6780(2) 0.053(2) Uani 1 d . .
H8 H 0.9863(7) 0.2442(3) 0.6780(2) 0.064 Uiso 1 calc R .
C9 C 0.9953(8) 0.3962(4) 0.6545(2) 0.055(2) Uani 1 d . .
H9 H 1.1176(8) 0.4100(4) 0.6532(2) 0.066 Uiso 1 calc R .
C10 C 0.8599(8) 0.4548(4) 0.6359(2) 0.0497(15) Uani 1 d . .
H10 H 0.8686(8) 0.5181(4) 0.6192(2) 0.060 Uiso 1 calc R .
C11 C 0.6888(7) 0.3975(3) 0.6476(2) 0.0410(14) Uani 1 d . .
C12 C 0.5272(6) 0.4200(3) 0.6073(2) 0.0399(13) Uani 1 d . .
C13 C 0.4604(7) 0.5167(3) 0.6024(2) 0.0510(15) Uani 1 d . .
H13 H 0.5115(7) 0.5667(3) 0.6271(2) 0.061 Uiso 1 calc R .
C14 C 0.3186(8) 0.5373(3) 0.5610(2) 0.0550(15) Uani 1 d . .
H14 H 0.2758(8) 0.6017(3) 0.5577(2) 0.066 Uiso 1 calc R .
C15 C 0.2394(7) 0.4643(4) 0.5243(2) 0.0534(15) Uani 1 d . .
H15 H 0.1450(7) 0.4796(4) 0.4962(2) 0.064 Uiso 1 calc R .
C16 C 0.3020(7) 0.3666(3) 0.5296(2) 0.0472(14) Uani 1 d . .
C17 C 0.4437(7) 0.3466(3) 0.5711(2) 0.0441(14) Uani 1 d . .
H17 H 0.4848(7) 0.2820(3) 0.5750(2) 0.053 Uiso 1 calc R .
C18 C 0.2180(7) 0.2879(3) 0.4886(2) 0.0536(15) Uani 1 d . .
C19 C 0.2126(7) 0.1035(4) 0.4813(2) 0.059(2) Uani 1 d . .
C20 C 0.1545(8) 0.0951(4) 0.4185(2) 0.074(2) Uani 1 d . .
H20 H 0.1250(8) 0.1505(4) 0.3944(2) 0.088 Uiso 1 calc R .
C21 C 0.1427(9) 0.0012(5) 0.3936(3) 0.094(2) Uani 1 d . .
H21 H 0.1037(9) -0.0075(5) 0.3519(3) 0.112 Uiso 1 calc R .
C22 C 0.1878(9) -0.0795(5) 0.4298(3) 0.094(2) Uani 1 d . .
H22 H 0.1826(9) -0.1426(5) 0.4125(3) 0.113 Uiso 1 calc R .
C23 C 0.2411(8) -0.0664(4) 0.4921(3) 0.075(2) Uani 1 d . .
C24 C 0.2934(9) -0.1501(4) 0.5358(3) 0.098(2) Uani 1 d . .
H24A H 0.3257(9) -0.1242(4) 0.5768(3) 0.117 Uiso 1 calc R .
H24B H 0.3941(9) -0.1849(4) 0.5193(3) 0.117 Uiso 1 calc R .
H24C H 0.1937(9) -0.1947(4) 0.5393(3) 0.117 Uiso 1 calc R .
H25 H 0.3479(102) 0.0348(53) 0.5847(42) 0.147(26) Uiso 1 d . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
O1 C1 1.214(6) . ?
O2 C1 1.315(6) . ?
O3 C4 1.241(6) . ?
O4 C7 1.222(6) . ?
O5 C8 1.438(6) . ?
O5 C11 1.454(5) . ?
O6 C18 1.215(5) . ?
N1 C4 1.359(7) . ?
N1 C7 1.392(6) . ?
N1 C3 1.467(7) . ?
N2 C18 1.377(6) . ?
N2 C19 1.404(6) . ?
N3 C19 1.339(6) . ?
N3 C23 1.368(6) . ?
C1 C2 1.483(7) . ?
C2 C3 1.515(7) . ?
C4 C5 1.520(7) . ?
C5 C6 1.538(7) . ?
C5 C8 1.549(7) . ?
C6 C7 1.483(8) . ?
C6 C11 1.583(6) . ?
C8 C9 1.508(7) . ?
C9 C10 1.332(7) . ?
C10 C11 1.518(7) . ?
C11 C12 1.486(6) . ?
C12 C17 1.389(6) . ?
C12 C13 1.403(6) . ?
C13 C14 1.381(7) . ?
C14 C15 1.380(7) . ?
C15 C16 1.406(7) . ?
C16 C17 1.379(6) . ?
C16 C18 1.499(7) . ?
C19 C20 1.392(7) . ?
C20 C21 1.379(8) . ?
C21 C22 1.371(9) . ?
C22 C23 1.380(9) . ?
C23 C24 1.508(9) . ?

loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C8 O5 C11 96.8(3) . . ?
C4 N1 C7 110.3(5) . . ?
C4 N1 C3 124.3(4) . . ?
C7 N1 C3 125.4(6) . . ?
C18 N2 C19 128.3(4) . . ?
C19 N3 C23 118.0(4) . . ?
O1 C1 O2 122.1(5) . . ?
O1 C1 C2 125.1(5) . . ?
O2 C1 C2 112.8(5) . . ?
C1 C2 C3 116.0(4) . . ?
N1 C3 C2 113.3(4) . . ?
O3 C4 N1 125.0(5) . . ?
O3 C4 C5 124.0(7) . . ?
N1 C4 C5 111.0(5) . . ?
C4 C5 C6 102.9(5) . . ?
C4 C5 C8 109.7(4) . . ?
C6 C5 C8 101.6(3) . . ?
C7 C6 C5 104.6(4) . . ?
C7 C6 C11 112.7(4) . . ?
C5 C6 C11 101.4(3) . . ?
O4 C7 N1 121.3(5) . . ?
O4 C7 C6 128.3(4) . . ?
N1 C7 C6 110.4(5) . . ?
O5 C8 C9 101.9(4) . . ?
O5 C8 C5 100.2(4) . . ?
C9 C8 C5 107.6(3) . . ?
C10 C9 C8 105.8(5) . . ?
C9 C10 C11 106.1(4) . . ?
O5 C11 C12 111.3(3) . . ?
O5 C11 C10 101.1(4) . . ?
C12 C11 C10 118.0(4) . . ?
O5 C11 C6 99.8(3) . . ?
C12 C11 C6 119.0(4) . . ?
C10 C11 C6 104.7(3) . . ?
C17 C12 C13 118.4(4) . . ?
C17 C12 C11 120.8(4) . . ?
C13 C12 C11 120.7(4) . . ?
C14 C13 C12 119.8(4) . . ?
C15 C14 C13 121.2(4) . . ?
C14 C15 C16 119.7(5) . . ?
C17 C16 C15 118.7(4) . . ?
C17 C16 C18 121.9(4) . . ?
C15 C16 C18 119.4(5) . . ?
C16 C17 C12 122.1(4) . . ?
O6 C18 N2 123.9(4) . . ?
O6 C18 C16 122.1(4) . . ?
N2 C18 C16 114.0(4) . . ?
N3 C19 C20 123.6(4) . . ?
N3 C19 N2 112.6(4) . . ?
C20 C19 N2 123.8(5) . . ?
C21 C20 C19 117.1(6) . . ?
C22 C21 C20 120.6(6) . . ?
C21 C22 C23 119.5(5) . . ?
N3 C23 C22 121.1(6) . . ?
N3 C23 C24 115.2(5) . . ?
C22 C23 C24 123.6(5) . . ?

_refine_diff_density_max    0.423
_refine_diff_density_min   -0.426
_refine_diff_density_rms    0.146 


