#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/37/2203788.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_2203788
loop_
_publ_author_name
'Pinkus, A. G.'
'Klausmeyer, Kevin K.'
'Feazell, Rodney P.'
'Jiro Tsuji'
_publ_section_title
N,N-[(Z,Z)-7,7-Diphenylbicyclo[4.1.0]hept-3-ene-2,5-diylidene]dibenzenesulfonamide
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o982
_journal_page_last               o984
_journal_paper_doi               10.1107/S1600536804010815
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C31 H24 N2 O4 S2'
_chemical_formula_moiety         'C31 H24 N2 O4 S2'
_chemical_formula_sum            'C31 H24 N2 O4 S2'
_chemical_formula_weight         552.64
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.405(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0546(3)
_cell_length_b                   23.3933(11)
_cell_length_c                   16.2515(9)
_cell_measurement_reflns_used    6775
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      30.15
_cell_measurement_theta_min      2.71
_cell_volume                     2619.4(2)
_computing_cell_refinement       Apex2
_computing_data_collection       'Apex2 (Bruker, 2003)'
_computing_data_reduction        'SAINT-PLUS (Bruker 2003)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2000)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker X8 APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            53078
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.74
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_type   'multi-scan; (Bruker, 2000)'
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.428
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5352
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0323
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0410P)²+1.5285P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0824
_refine_ls_wR_factor_ref         0.0871
_reflns_number_gt                4696
_reflns_number_total             5352
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            na6324.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2203788
_cod_database_fobs_code          2203788
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'
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_type_symbol
C1 0.71050(18) 0.22084(6) 0.43335(8) 0.0173(3) Uani d . 1 C
C2 0.6345(2) 0.25590(6) 0.49359(9) 0.0197(3) Uani d . 1 C
H2 0.6053 0.2383 0.5407 0.024 Uiso calc R 1 H
C3 0.6051(2) 0.31231(6) 0.48375(9) 0.0203(3) Uani d . 1 C
H3 0.5541 0.3320 0.5237 0.024 Uiso calc R 1 H
C4 0.64991(19) 0.34422(6) 0.41283(9) 0.0184(3) Uani d . 1 C
C5 0.75099(19) 0.31425(6) 0.35417(9) 0.0168(3) Uani d . 1 C
H5 0.7210 0.3280 0.2959 0.020 Uiso calc R 1 H
C6 0.78275(19) 0.24985(6) 0.36497(8) 0.0168(3) Uani d . 1 C
H6 0.7705 0.2280 0.3126 0.020 Uiso calc R 1 H
C7 0.95601(19) 0.29081(6) 0.38538(8) 0.0168(3) Uani d . 1 C
C8 1.08361(19) 0.29257(6) 0.32126(8) 0.0178(3) Uani d . 1 C
C9 1.1868(2) 0.24404(6) 0.30670(9) 0.0220(3) Uani d . 1 C
H9 1.1757 0.2104 0.3357 0.026 Uiso calc R 1 H
C10 1.3065(2) 0.24592(7) 0.24875(10) 0.0262(3) Uani d . 1 C
H10 1.3742 0.2134 0.2389 0.031 Uiso calc R 1 H
C11 1.3248(2) 0.29624(7) 0.20575(9) 0.0276(3) Uani d . 1 C
H11 1.4044 0.2974 0.1670 0.033 Uiso calc R 1 H
C12 1.2245(2) 0.34486(8) 0.22065(10) 0.0297(4) Uani d . 1 C
H12 1.2376 0.3786 0.1922 0.036 Uiso calc R 1 H
C13 1.1036(2) 0.34302(7) 0.27841(9) 0.0244(3) Uani d . 1 C
H13 1.0362 0.3756 0.2883 0.029 Uiso calc R 1 H
C14 1.06556(19) 0.30019(6) 0.47480(8) 0.0180(3) Uani d . 1 C
C15 1.1034(2) 0.35587(6) 0.50514(9) 0.0218(3) Uani d . 1 C
H15 1.0536 0.3868 0.4714 0.026 Uiso calc R 1 H
C16 1.2153(2) 0.36514(7) 0.58563(10) 0.0262(3) Uani d . 1 C
H16 1.2388 0.4022 0.6059 0.031 Uiso calc R 1 H
C17 1.2921(2) 0.31891(7) 0.63587(9) 0.0267(3) Uani d . 1 C
H17 1.3676 0.3251 0.6895 0.032 Uiso calc R 1 H
C18 1.2560(2) 0.26352(7) 0.60593(9) 0.0253(3) Uani d . 1 C
H18 1.3073 0.2327 0.6396 0.030 Uiso calc R 1 H
C19 1.1429(2) 0.25400(6) 0.52549(9) 0.0209(3) Uani d . 1 C
H19 1.1190 0.2168 0.5056 0.025 Uiso calc R 1 H
C20 0.7410(2) 0.05486(6) 0.42213(9) 0.0205(3) Uani d . 1 C
C21 0.7919(2) 0.04525(7) 0.50878(10) 0.0242(3) Uani d . 1 C
H21 0.8415 0.0747 0.5456 0.029 Uiso calc R 1 H
C22 0.7669(2) -0.00920(7) 0.53884(10) 0.0292(3) Uani d . 1 C
H22 0.7979 -0.0163 0.5965 0.035 Uiso calc R 1 H
C23 0.6960(2) -0.05302(7) 0.48319(11) 0.0309(4) Uani d . 1 C
H23 0.6799 -0.0894 0.5038 0.037 Uiso calc R 1 H
C24 0.6492(2) -0.04316(7) 0.39739(11) 0.0303(4) Uani d . 1 C
H24 0.6039 -0.0730 0.3606 0.036 Uiso calc R 1 H
C25 0.6696(2) 0.01135(6) 0.36579(10) 0.0251(3) Uani d . 1 C
H25 0.6361 0.0184 0.3082 0.030 Uiso calc R 1 H
C26 0.4632(2) 0.49457(6) 0.33871(9) 0.0206(3) Uani d . 1 C
C27 0.3518(2) 0.49614(6) 0.39992(10) 0.0262(3) Uani d . 1 C
H27 0.3663 0.4682 0.4415 0.031 Uiso calc R 1 H
C28 0.2187(2) 0.54023(7) 0.39761(10) 0.0269(3) Uani d . 1 C
H28 0.1435 0.5419 0.4380 0.032 Uiso calc R 1 H
C29 0.1974(2) 0.58164(7) 0.33557(10) 0.0259(3) Uani d . 1 C
H29 0.1085 0.6111 0.3347 0.031 Uiso calc R 1 H
C30 0.3081(2) 0.57947(7) 0.27458(10) 0.0290(3) Uani d . 1 C
H30 0.2921 0.6072 0.2327 0.035 Uiso calc R 1 H
C31 0.4428(2) 0.53597(7) 0.27600(9) 0.0249(3) Uani d . 1 C
H31 0.5182 0.5345 0.2356 0.030 Uiso calc R 1 H
N1 0.70278(17) 0.16598(5) 0.44514(7) 0.0192(2) Uani d . 1 N
N2 0.59438(18) 0.39709(5) 0.40807(8) 0.0226(3) Uani d . 1 N
O1 0.66538(17) 0.12614(4) 0.29626(7) 0.0286(2) Uani d . 1 O
O2 0.99008(15) 0.13034(4) 0.39007(7) 0.0272(2) Uani d . 1 O
O3 0.83147(17) 0.46701(5) 0.37479(10) 0.0450(3) Uani d . 1 O
O4 0.6184(2) 0.42025(5) 0.25395(8) 0.0386(3) Uani d . 1 O
S1 0.78370(5) 0.121888(14) 0.37991(2) 0.01941(9) Uani d . 1 S
S2 0.64494(5) 0.442814(15) 0.33813(3) 0.02583(10) Uani d . 1 S
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'
N N 0.0061 0.0033 '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'
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
_geom_angle_publ_flag
N1 C1 C2 114.91(12) ?
N1 C1 C6 126.45(12) ?
C2 C1 C6 118.62(12) ?
C3 C2 C1 122.76(13) ?
C3 C2 H2 118.6 ?
C1 C2 H2 118.6 ?
C2 C3 C4 122.84(13) ?
C2 C3 H3 118.6 ?
C4 C3 H3 118.6 ?
N2 C4 C3 114.87(12) ?
N2 C4 C5 126.45(13) ?
C3 C4 C5 118.68(12) ?
C4 C5 C6 118.10(11) ?
C4 C5 C7 120.51(12) ?
C6 C5 C7 60.19(9) yes
C4 C5 H5 115.6 ?
C6 C5 H5 115.6 ?
C7 C5 H5 115.6 ?
C1 C6 C5 118.16(11) ?
C1 C6 C7 120.70(11) ?
C5 C6 C7 59.91(8) yes
C1 C6 H6 115.6 ?
C5 C6 H6 115.6 ?
C7 C6 H6 115.6 ?
C14 C7 C8 113.64(11) yes
C14 C7 C5 121.35(11) ?
C8 C7 C5 114.92(11) ?
C14 C7 C6 121.29(11) ?
C8 C7 C6 115.58(11) ?
C5 C7 C6 59.90(9) yes
C13 C8 C9 119.47(13) ?
C13 C8 C7 120.35(12) ?
C9 C8 C7 120.16(13) ?
C10 C9 C8 120.16(14) ?
C10 C9 H9 119.9 ?
C8 C9 H9 119.9 ?
C11 C10 C9 120.14(14) ?
C11 C10 H10 119.9 ?
C9 C10 H10 119.9 ?
C12 C11 C10 120.03(14) ?
C12 C11 H11 120.0 ?
C10 C11 H11 120.0 ?
C11 C12 C13 119.96(15) ?
C11 C12 H12 120.0 ?
C13 C12 H12 120.0 ?
C8 C13 C12 120.24(14) ?
C8 C13 H13 119.9 ?
C12 C13 H13 119.9 ?
C19 C14 C15 119.47(13) ?
C19 C14 C7 120.68(13) ?
C15 C14 C7 119.66(13) ?
C16 C15 C14 120.22(14) ?
C16 C15 H15 119.9 ?
C14 C15 H15 119.9 ?
C15 C16 C17 120.04(14) ?
C15 C16 H16 120.0 ?
C17 C16 H16 120.0 ?
C18 C17 C16 120.02(14) ?
C18 C17 H17 120.0 ?
C16 C17 H17 120.0 ?
C17 C18 C19 120.15(14) ?
C17 C18 H18 119.9 ?
C19 C18 H18 119.9 ?
C18 C19 C14 120.09(14) ?
C18 C19 H19 120.0 ?
C14 C19 H19 120.0 ?
C25 C20 C21 121.71(14) ?
C25 C20 S1 117.59(11) ?
C21 C20 S1 120.52(12) ?
C22 C21 C20 118.58(15) ?
C22 C21 H21 120.7 ?
C20 C21 H21 120.7 ?
C23 C22 C21 120.23(15) ?
C23 C22 H22 119.9 ?
C21 C22 H22 119.9 ?
C24 C23 C22 120.60(14) ?
C24 C23 H23 119.7 ?
C22 C23 H23 119.7 ?
C23 C24 C25 120.24(16) ?
C23 C24 H24 119.9 ?
C25 C24 H24 119.9 ?
C20 C25 C24 118.62(15) ?
C20 C25 H25 120.7 ?
C24 C25 H25 120.7 ?
C31 C26 C27 121.27(13) ?
C31 C26 S2 115.75(11) ?
C27 C26 S2 122.91(12) ?
C28 C27 C26 118.77(14) ?
C28 C27 H27 120.6 ?
C26 C27 H27 120.6 ?
C29 C28 C27 120.42(14) ?
C29 C28 H28 119.8 ?
C27 C28 H28 119.8 ?
C28 C29 C30 120.36(14) ?
C28 C29 H29 119.8 ?
C30 C29 H29 119.8 ?
C29 C30 C31 120.16(14) ?
C29 C30 H30 119.9 ?
C31 C30 H30 119.9 ?
C30 C31 C26 119.01(14) ?
C30 C31 H31 120.5 ?
C26 C31 H31 120.5 ?
C1 N1 S1 119.11(10) ?
C4 N2 S2 123.46(10) ?
O1 S1 O2 117.72(7) ?
O1 S1 N1 110.51(6) ?
O2 S1 N1 108.52(6) ?
O1 S1 C20 108.45(7) ?
O2 S1 C20 109.27(7) ?
N1 S1 C20 101.09(6) ?
O3 S2 O4 117.26(8) ?
O3 S2 N2 106.42(7) ?
O4 S2 N2 114.35(7) ?
O3 S2 C26 109.20(7) ?
O4 S2 C26 108.07(7) ?
N2 S2 C26 100.11(7) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 1.3006(18) ?
C1 C2 1.4645(19) yes
C1 C6 1.4827(19) yes
C2 C3 1.340(2) yes
C2 H2 0.9300 ?
C3 C4 1.4635(19) yes
C3 H3 0.9300 ?
C4 N2 1.2947(18) ?
C4 C5 1.4835(18) yes
C5 C6 1.5278(19) yes
C5 C7 1.5281(18) yes
C5 H5 0.9800 ?
C6 C7 1.5323(18) yes
C6 H6 0.9800 ?
C7 C14 1.5082(19) ?
C7 C8 1.5168(18) ?
C8 C13 1.393(2) ?
C8 C9 1.396(2) ?
C9 C10 1.394(2) ?
C9 H9 0.9300 ?
C10 C11 1.389(2) ?
C10 H10 0.9300 ?
C11 C12 1.388(2) ?
C11 H11 0.9300 ?
C12 C13 1.398(2) ?
C12 H12 0.9300 ?
C13 H13 0.9300 ?
C14 C19 1.397(2) ?
C14 C15 1.398(2) ?
C15 C16 1.392(2) ?
C15 H15 0.9300 ?
C16 C17 1.393(2) ?
C16 H16 0.9300 ?
C17 C18 1.388(2) ?
C17 H17 0.9300 ?
C18 C19 1.395(2) ?
C18 H18 0.9300 ?
C19 H19 0.9300 ?
C20 C25 1.389(2) ?
C20 C21 1.395(2) ?
C20 S1 1.7632(14) ?
C21 C22 1.389(2) ?
C21 H21 0.9300 ?
C22 C23 1.387(2) ?
C22 H22 0.9300 ?
C23 C24 1.382(2) ?
C23 H23 0.9300 ?
C24 C25 1.394(2) ?
C24 H24 0.9300 ?
C25 H25 0.9300 ?
C26 C31 1.391(2) ?
C26 C27 1.394(2) ?
C26 S2 1.7652(14) ?
C27 C28 1.390(2) ?
C27 H27 0.9300 ?
C28 C29 1.383(2) ?
C28 H28 0.9300 ?
C29 C30 1.388(2) ?
C29 H29 0.9300 ?
C30 C31 1.389(2) ?
C30 H30 0.9300 ?
C31 H31 0.9300 ?
N1 S1 1.6653(12) ?
N2 S2 1.6545(13) ?
O1 S1 1.4378(11) ?
O2 S1 1.4433(11) ?
O3 S2 1.4388(13) ?
O4 S2 1.4406(13) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C5 H5 O4 0.98 2.33 3.004(2) 125 yes
C6 H6 O1 0.98 2.49 3.148(2) 124 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4513601
2 PubChem 139066757
