# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2004



data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
#==============================================================================

_publ_contact_author_name        'Prof Dietmar Kuck'
_publ_contact_author_address     
;
Fakultat fur Chemie
Universitat Bielefeld
Universitastrasse 25
Bielefeld
D-33615
GERMANY
;

_publ_contact_author_email       DIETMAR.KUCK@UNI-BIELEFELD.DE

_publ_section_title              
;
Methoxy-substituted centrohexaindanes through the
fenestrane route
;

# The loop structure below should contain the names and addresses of all
# authors, in the required order of publication. Repeat as necessary.

loop_
_publ_author_name
_publ_author_address
J.Tellenbroker
;     Fakultat f. Chemie
Universitat Bielefeld
33615 Bielefeld
Germany
;
D.Barth
;     Fakultat f. Chemie
Universitat Bielefeld
33615 Bielefeld
Germany
;
B.Neumann
;     Fakultat f. Chemie
Universitat Bielefeld
33615 Bielefeld
Germany
;
H.-G.Stammler
;     Fakultat f. Chemie
Universitat Bielefeld
33615 Bielefeld
Germany
;
D.Kuck
;     Fakultat f. Chemie
Universitat Bielefeld
33615 Bielefeld
Germany
;

#=========================================================================

data_compound7
_database_code_depnum_ccdc_archive 'CCDC 250182'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_formula_moiety         'C45 H32 O4 . H2 O . C H3 OH'
_chemical_formula_sum            'C46 H38 O6'
_chemical_formula_weight         686.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pnma

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

_cell_length_a                   17.357(8)
_cell_length_b                   13.487(5)
_cell_length_c                   14.830(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3472(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    36
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      8.4

_exptl_crystal_description       octahedral
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1448
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Siemens P2(1) diffractometer'
_diffrn_measurement_method       Wyckoff-scan
_diffrn_refln_scan_width         2.4
_diffrn_standards_number         2
_diffrn_standards_interval_count 100
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3185
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0646
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3185
_reflns_number_gt                1971
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'P3 (1989)'
_computing_cell_refinement       'P3 (1989)'
_computing_data_reduction        'SHELXTL-PLUS (1990)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL-PLUS (1990)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) 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^)+(0.1005P)^2^+5.0304P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3185
_refine_ls_number_parameters     251
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1294
_refine_ls_R_factor_gt           0.0753
_refine_ls_wR_factor_ref         0.2126
_refine_ls_wR_factor_gt          0.1787
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0212(2) 0.2500 0.7095(3) 0.0323(10) Uani 1 d S . .
O2 O 0.1606(2) 0.2500 0.7684(2) 0.0327(10) Uani 1 d S . .
O3 O 0.35137(16) 0.1543(2) -0.00610(17) 0.0305(7) Uani 1 d . . .
C1 C 0.2081(3) 0.2500 0.3595(4) 0.0217(12) Uani 1 d S . .
C2 C 0.1211(3) 0.2500 0.3865(3) 0.0217(12) Uani 1 d S . .
C3 C 0.1241(3) 0.2500 0.4908(3) 0.0228(12) Uani 1 d S . .
C4 C 0.1997(3) 0.2500 0.5227(4) 0.0218(12) Uani 1 d S . .
C5 C 0.2590(3) 0.2500 0.4464(3) 0.0224(12) Uani 1 d S . .
C6 C 0.3038(2) 0.1534(3) 0.4386(2) 0.0228(9) Uani 1 d . . .
C7 C 0.2844(2) 0.1007(3) 0.3603(2) 0.0229(9) Uani 1 d . . .
C8 C 0.2254(2) 0.1561(3) 0.3027(2) 0.0206(8) Uani 1 d . . .
C9 C 0.1473(2) 0.1062(3) 0.2930(2) 0.0236(9) Uani 1 d . . .
C10 C 0.0899(2) 0.1561(3) 0.3431(2) 0.0226(9) Uani 1 d . . .
C11 C 0.0625(3) 0.2500 0.5508(3) 0.0255(13) Uani 1 d S . .
H11 H 0.0111 0.2500 0.5289 0.031 Uiso 1 calc SR . .
C12 C 0.0766(3) 0.2500 0.6436(4) 0.0258(13) Uani 1 d S . .
C13 C 0.1537(3) 0.2500 0.6760(4) 0.0259(13) Uani 1 d S . .
C14 C 0.2147(3) 0.2500 0.6158(4) 0.0255(13) Uani 1 d S . .
H14 H 0.2663 0.2500 0.6373 0.031 Uiso 1 calc SR . .
C15 C 0.3568(2) 0.1137(3) 0.4995(3) 0.0319(10) Uani 1 d . . .
H15 H 0.3708 0.1495 0.5521 0.038 Uiso 1 calc R . .
C16 C 0.3892(2) 0.0204(4) 0.4821(3) 0.0373(11) Uani 1 d . . .
H16 H 0.4248 -0.0076 0.5236 0.045 Uiso 1 calc R . .
C17 C 0.3696(3) -0.0311(3) 0.4046(3) 0.0378(11) Uani 1 d . . .
H17 H 0.3921 -0.0941 0.3933 0.045 Uiso 1 calc R . .
C18 C 0.3172(2) 0.0084(3) 0.3429(3) 0.0287(9) Uani 1 d . . .
H18 H 0.3041 -0.0272 0.2898 0.034 Uiso 1 calc R . .
C19 C 0.1284(2) 0.0234(3) 0.2414(3) 0.0281(9) Uani 1 d . . .
H19 H 0.1668 -0.0096 0.2070 0.034 Uiso 1 calc R . .
C20 C 0.0527(2) -0.0107(3) 0.2406(3) 0.0325(10) Uani 1 d . . .
H20 H 0.0392 -0.0667 0.2051 0.039 Uiso 1 calc R . .
C21 C -0.0033(2) 0.0371(3) 0.2920(3) 0.0359(11) Uani 1 d . . .
H21 H -0.0545 0.0123 0.2920 0.043 Uiso 1 calc R . .
C22 C 0.0145(2) 0.1208(3) 0.3435(3) 0.0290(9) Uani 1 d . . .
H22 H -0.0241 0.1530 0.3781 0.035 Uiso 1 calc R . .
C23 C -0.0573(3) 0.2500 0.6804(4) 0.0318(14) Uani 1 d S . .
H23A H -0.0913 0.2500 0.7331 0.048 Uiso 1 calc SR . .
H23B H -0.0672 0.1907 0.6440 0.048 Uiso 0.50 calc PR . .
H23C H -0.0672 0.3093 0.6440 0.048 Uiso 0.50 calc PR . .
C24 C 0.2366(3) 0.2500 0.8058(4) 0.0304(14) Uani 1 d S . .
H24A H 0.2334 0.2500 0.8718 0.046 Uiso 1 calc SR . .
H24B H 0.2643 0.3093 0.7856 0.046 Uiso 0.50 calc PR . .
H24C H 0.2643 0.1907 0.7856 0.046 Uiso 0.50 calc PR . .
C25 C 0.2583(2) 0.1988(3) 0.2150(2) 0.0228(8) Uani 1 d . . .
C26 C 0.2880(2) 0.1455(3) 0.1414(2) 0.0240(9) Uani 1 d . . .
H26 H 0.2872 0.0751 0.1413 0.029 Uiso 1 calc R . .
C27 C 0.3185(2) 0.1973(3) 0.0685(2) 0.0239(9) Uani 1 d . . .
C28 C 0.3528(3) 0.0476(3) -0.0086(3) 0.0353(11) Uani 1 d . . .
H28A H 0.3824 0.0225 0.0429 0.053 Uiso 1 calc R . .
H28B H 0.3770 0.0254 -0.0648 0.053 Uiso 1 calc R . .
H28C H 0.3000 0.0221 -0.0055 0.053 Uiso 1 calc R . .
O4 O -0.0035(3) 0.2500 0.8932(4) 0.0684(16) Uiso 1 d S . .
O5 O 0.0879(6) 0.2500 1.0456(8) 0.154(4) Uiso 1 d S . .
C29 C 0.0338(7) 0.2500 1.1195(8) 0.100(4) Uiso 1 d S . .


_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 C12 1.370(6) . Y
O1 C23 1.428(7) . Y
O2 C13 1.375(6) . Y
O2 C24 1.432(7) . Y
O3 C27 1.374(4) . Y
O3 C28 1.440(5) . Y
C1 C8 1.550(5) 7_565 Y
C1 C8 1.550(5) . Y
C1 C5 1.562(7) . Y
C1 C2 1.563(7) . Y
C2 C10 1.521(5) . Y
C2 C10 1.521(5) 7_565 Y
C2 C3 1.546(7) . Y
C3 C11 1.392(7) . Y
C3 C4 1.395(7) . Y
C4 C14 1.405(8) . Y
C4 C5 1.529(7) . Y
C5 C6 1.522(5) 7_565 Y
C5 C6 1.522(5) . Y
C6 C15 1.395(5) . Y
C6 C7 1.402(5) . Y
C7 C18 1.393(5) . Y
C7 C8 1.528(5) . Y
C8 C9 1.521(5) . Y
C8 C25 1.532(5) . Y
C9 C19 1.393(6) . Y
C9 C10 1.414(5) . Y
C10 C22 1.392(5) . Y
C11 C12 1.397(7) . Y
C12 C13 1.423(8) . Y
C13 C14 1.384(8) . Y
C15 C16 1.402(6) . Y
C16 C17 1.385(6) . Y
C17 C18 1.395(6) . Y
C19 C20 1.391(6) . Y
C20 C21 1.393(6) . Y
C21 C22 1.398(6) . Y
C25 C25 1.382(8) 7_565 Y
C25 C26 1.404(5) . Y
C26 C27 1.391(5) . Y
C27 C27 1.422(8) 7_565 Y
O5 C29 1.443(14) . Y

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
C12 O1 C23 117.0(4) . . Y
C13 O2 C24 117.8(4) . . Y
C27 O3 C28 116.7(3) . . Y
C8 C1 C8 109.6(4) 7_565 . Y
C8 C1 C5 109.8(3) 7_565 . Y
C8 C1 C5 109.8(3) . . Y
C8 C1 C2 109.1(3) 7_565 . Y
C8 C1 C2 109.1(3) . . Y
C5 C1 C2 109.5(4) . . Y
C10 C2 C10 112.7(4) . 7_565 Y
C10 C2 C3 115.8(3) . . Y
C10 C2 C3 115.8(3) 7_565 . Y
C10 C2 C1 103.7(3) . . Y
C10 C2 C1 103.7(3) 7_565 . Y
C3 C2 C1 103.0(4) . . Y
C11 C3 C4 120.4(5) . . Y
C11 C3 C2 127.9(5) . . Y
C4 C3 C2 111.7(5) . . Y
C3 C4 C14 120.5(5) . . Y
C3 C4 C5 112.5(5) . . Y
C14 C4 C5 127.0(5) . . Y
C6 C5 C6 117.8(4) 7_565 . Y
C6 C5 C4 113.6(3) 7_565 . Y
C6 C5 C4 113.6(3) . . Y
C6 C5 C1 103.1(3) 7_565 . Y
C6 C5 C1 103.1(3) . . Y
C4 C5 C1 103.3(4) . . Y
C15 C6 C7 120.0(4) . . Y
C15 C6 C5 128.1(4) . . Y
C7 C6 C5 111.9(3) . . Y
C18 C7 C6 120.5(4) . . Y
C18 C7 C8 127.4(4) . . Y
C6 C7 C8 112.1(3) . . Y
C9 C8 C7 115.7(3) . . Y
C9 C8 C25 114.7(3) . . Y
C7 C8 C25 114.1(3) . . Y
C9 C8 C1 103.9(3) . . Y
C7 C8 C1 103.0(3) . . Y
C25 C8 C1 103.1(3) . . Y
C19 C9 C10 120.3(4) . . Y
C19 C9 C8 128.1(3) . . Y
C10 C9 C8 111.6(3) . . Y
C22 C10 C9 120.1(4) . . Y
C22 C10 C2 128.2(4) . . Y
C9 C10 C2 111.6(3) . . Y
C3 C11 C12 119.7(5) . . Y
O1 C12 C11 125.4(5) . . Y
O1 C12 C13 114.8(5) . . Y
C11 C12 C13 119.8(5) . . Y
O2 C13 C14 125.2(5) . . Y
O2 C13 C12 114.6(5) . . Y
C14 C13 C12 120.2(5) . . Y
C13 C14 C4 119.4(5) . . Y
C6 C15 C16 119.3(4) . . Y
C17 C16 C15 120.3(4) . . Y
C16 C17 C18 120.8(4) . . Y
C7 C18 C17 119.1(4) . . Y
C20 C19 C9 119.5(4) . . Y
C19 C20 C21 120.1(4) . . Y
C20 C21 C22 121.2(4) . . Y
C10 C22 C21 118.8(4) . . Y
C25 C25 C26 120.8(2) 7_565 . Y
C25 C25 C8 112.0(2) 7_565 . Y
C26 C25 C8 127.2(3) . . Y
C27 C26 C25 119.1(4) . . Y
O3 C27 C26 124.9(4) . . Y
O3 C27 C27 115.0(2) . 7_565 Y
C26 C27 C27 120.1(2) . 7_565 Y

_diffrn_measured_fraction_theta_max 0.932
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.932
_refine_diff_density_max         1.207
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.074



