#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/02/2100224.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2100224
loop_
_publ_author_name
'Edwards, David J.'
'Pritchard, Robin G.'
'Wallace, Timothy W.'
_publ_section_title
;
 Fine-tuning of biaryl dihedral angles: structural characterization of
 five homologous three-atom bridged biphenyls by X-ray crystallography
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              335
_journal_page_last               345
_journal_paper_doi               10.1107/S0108768105006713
_journal_volume                  61
_journal_year                    2005
_chemical_formula_moiety         'C20 H24 O6 S1'
_chemical_formula_sum            'C20 H24 O6 S'
_chemical_formula_weight         392.45
_chemical_name_systematic
;
5,7-dihydro-1,2,3,9,10,11-hexamethoxydibenzo[c,e]thiepine
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 104.0380
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6029(2)
_cell_length_b                   12.2965(3)
_cell_length_c                   17.6032(4)
_cell_measurement_reflns_used    10338
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1806.55(7)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15259
_diffrn_reflns_reduction_process
;
 Scaled and merged with SORTAV
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        29.12
_diffrn_reflns_theta_max         29.12
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  1.016
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.301
_refine_ls_extinction_coef       0.0074(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2388
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0508P)²+1.3323P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.0992
_reflns_number_gt                2003
_reflns_number_total             2388
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            sx5028.cif
_cod_data_source_block           sulfide
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2100224
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 0.55184(14) 0.58168(9) 0.66847(7) 0.0135(3) Uani d . 1 . . C
C2 0.65913(15) 0.58284(9) 0.62049(7) 0.0142(3) Uani d . 1 . . C
C3 0.77012(15) 0.49775(10) 0.62572(7) 0.0146(3) Uani d . 1 . . C
C4 0.77115(15) 0.41306(10) 0.67830(7) 0.0146(3) Uani d . 1 . . C
C4A 0.66397(15) 0.41269(9) 0.72640(7) 0.0138(3) Uani d . 1 . . C
C5 0.66577(16) 0.32012(10) 0.78250(8) 0.0163(3) Uani d . 1 . . C
C11B 0.55516(14) 0.49830(9) 0.72330(7) 0.0138(3) Uani d . 1 . . C
C12 0.28299(17) 0.63325(13) 0.62107(10) 0.0263(3) Uani d . 1 . . C
C13 0.5804(2) 0.65199(13) 0.49157(8) 0.0279(3) Uani d . 1 . . C
C14 0.98301(18) 0.41644(12) 0.58250(9) 0.0251(3) Uani d . 1 . . C
O1 0.44194(11) 0.66526(7) 0.66090(5) 0.0177(2) Uani d . 1 . . O
O2 0.66061(11) 0.66986(7) 0.57123(5) 0.0178(2) Uani d . 1 . . O
O3 0.87013(11) 0.50350(7) 0.57639(5) 0.0193(2) Uani d . 1 . . O
S6 0.5 0.22488(3) 0.75 0.01952(15) Uani d S 1 . . S
H14B 1.044(2) 0.4347(14) 0.5450(10) 0.031(5) Uiso d . 1 . . H
H4 0.847(2) 0.3561(14) 0.6814(10) 0.023(4) Uiso d . 1 . . H
H14A 0.928(2) 0.3476(15) 0.5698(10) 0.031(5) Uiso d . 1 . . H
H13C 0.594(2) 0.7161(15) 0.4628(11) 0.030(5) Uiso d . 1 . . H
H8B 0.6576(18) 0.3479(13) 0.8335(9) 0.019(4) Uiso d . 1 . . H
H8A 0.759(2) 0.2756(13) 0.7889(9) 0.020(4) Uiso d . 1 . . H
H14C 1.058(2) 0.4178(14) 0.6363(11) 0.027(4) Uiso d . 1 . . H
H12A 0.280(3) 0.6008(19) 0.5714(14) 0.055(6) Uiso d . 1 . . H
H13B 0.465(3) 0.6393(18) 0.4877(13) 0.051(6) Uiso d . 1 . . H
H12C 0.211(3) 0.6965(17) 0.6134(11) 0.043(5) Uiso d . 1 . . H
H13A 0.629(3) 0.591(2) 0.4700(14) 0.065(7) Uiso d . 1 . . H
H12B 0.241(3) 0.5780(19) 0.6481(14) 0.059(7) Uiso d . 1 . . H
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
O1 C1 C2 . 118.19(10)
O1 C1 C11B . 120.61(11)
C2 C1 C11B . 121.20(11)
O2 C2 C1 . 119.81(11)
O2 C2 C3 . 120.63(11)
C1 C2 C3 . 119.48(11)
O3 C3 C4 . 123.97(11)
O3 C3 C2 . 116.31(11)
C4 C3 C2 . 119.71(11)
C3 C4 C4A . 120.50(11)
C3 C4 H4 . 119.1(10)
C4A C4 H4 . 120.4(10)
C4 C4A C11B . 120.52(11)
C4 C4A C5 . 119.85(11)
C11B C4A C5 . 119.63(11)
C4A C5 S6 . 113.36(9)
C4A C5 H8B . 110.3(9)
S6 C5 H8B . 106.6(9)
C4A C5 H8A . 112.6(10)
S6 C5 H8A . 104.0(10)
H8B C5 H8A . 109.7(13)
C4A C11B C1 . 118.52(11)
C4A C11B C11B 2_656 119.84(9)
C1 C11B C11B 2_656 121.63(9)
O1 C12 H12A . 111.7(14)
O1 C12 H12C . 110.3(12)
H12A C12 H12C . 109.3(17)
O1 C12 H12B . 112.8(14)
H12A C12 H12B . 103.4(19)
H12C C12 H12B . 109.0(18)
O2 C13 H13C . 107.5(11)
O2 C13 H13B . 109.3(13)
H13C C13 H13B . 110.0(17)
O2 C13 H13A . 110.5(14)
H13C C13 H13A . 107.7(18)
H13B C13 H13A . 111.8(19)
O3 C14 H14B . 104.4(11)
O3 C14 H14A . 110.6(11)
H14B C14 H14A . 111.3(15)
O3 C14 H14C . 109.1(10)
H14B C14 H14C . 107.7(14)
H14A C14 H14C . 113.4(14)
C1 O1 C12 . 113.13(10)
C2 O2 C13 . 115.07(10)
C3 O3 C14 . 115.74(10)
C5 S6 C5 2_656 100.25(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 . 1.3809(14) ?
C1 C2 . 1.3942(17) ?
C1 C11B . 1.4037(16) ?
C2 O2 . 1.3792(14) ?
C2 C3 . 1.4044(17) ?
C3 O3 . 1.3644(15) ?
C3 C4 . 1.3919(17) ?
C4 C4A . 1.3949(17) ?
C4 H4 . 0.947(17) ?
C4A C11B . 1.4010(17) ?
C4A C5 . 1.5046(17) ?
C5 S6 . 1.8267(13) ?
C5 H8B . 0.980(16) ?
C5 H8A . 0.958(17) ?
C11B C11B 2_656 1.489(2) ?
C12 O1 . 1.4323(17) ?
C12 H12A . 0.96(2) ?
C12 H12C . 0.99(2) ?
C12 H12B . 0.95(2) ?
C13 O2 . 1.4218(16) ?
C13 H13C . 0.960(18) ?
C13 H13B . 0.99(2) ?
C13 H13A . 0.98(3) ?
C14 O3 . 1.4318(16) ?
C14 H14B . 0.967(18) ?
C14 H14A . 0.969(18) ?
C14 H14C . 1.010(18) ?
S6 C5 2_656 1.8267(13) ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_4
_geom_torsion
O1 C1 C2 O2 . 4.46(17)
C11B C1 C2 O2 . -175.30(11)
O1 C1 C2 C3 . -178.70(10)
C11B C1 C2 C3 . 1.53(18)
O2 C2 C3 O3 . -3.94(17)
C1 C2 C3 O3 . 179.25(10)
O2 C2 C3 C4 . 177.19(11)
C1 C2 C3 C4 . 0.38(18)
O3 C3 C4 C4A . -179.48(11)
C2 C3 C4 C4A . -0.70(19)
C3 C4 C4A C11B . -0.89(19)
C3 C4 C4A C5 . 179.54(11)
C4 C4A C5 S6 . -104.20(12)
C11B C4A C5 S6 . 76.23(13)
C4 C4A C11B C1 . 2.73(18)
C5 C4A C11B C1 . -177.70(11)
C4 C4A C11B C11B 2_656 -178.19(12)
C5 C4A C11B C11B 2_656 1.38(19)
O1 C1 C11B C4A . 177.17(10)
C2 C1 C11B C4A . -3.07(18)
O1 C1 C11B C11B 2_656 -1.89(19)
C2 C1 C11B C11B 2_656 177.87(12)
C2 C1 O1 C12 . 105.35(13)
C11B C1 O1 C12 . -74.88(15)
C1 C2 O2 C13 . -101.06(14)
C3 C2 O2 C13 . 82.14(15)
C4 C3 O3 C14 . -1.37(18)
C2 C3 O3 C14 . 179.81(11)
C4A C5 S6 C5 2_656 -44.52(7)
