#------------------------------------------------------------------------------
#$Date: 2025-08-22 16:55:42 +0200 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/7/21/61/7216187.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7216187
loop_
_publ_author_name
'Ballie, Laura'
'Farrugia, Louis J.'
'MacNicol, David D.'
'MacSween, Ross'
_publ_section_title
;
 2,7-di-p-Chlorobenzoylnaphtho[2?3?-4 : 5]thiepin: a conformationally
 flexible new host molecule showing solvatochromic effects
;
_journal_issue                   58
_journal_name_full               CrystEngComm
_journal_page_first              326
_journal_paper_doi               10.1039/b414315a
_journal_volume                  6
_journal_year                    2004
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C28 H16 Cl2 O2 S, 0.5(C6 H6)'
_chemical_formula_sum            'C31 H19 Cl2 O2 S'
_chemical_formula_weight         526.42
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_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_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2004-02-27T17:15:42-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 91.1170(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   33.3796(10)
_cell_length_b                   10.1112(2)
_cell_length_c                   14.2492(4)
_cell_measurement_reflns_used    12248
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.987
_cell_measurement_theta_min      2.2
_cell_measurement_wavelength     0.71073
_cell_volume                     4808.3(2)
_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-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.180302E-1
_diffrn_orient_matrix_UB_12      0.789918E-1
_diffrn_orient_matrix_UB_13      0.7987E-3
_diffrn_orient_matrix_UB_21      -0.200432E-1
_diffrn_orient_matrix_UB_22      0.498637E-1
_diffrn_orient_matrix_UB_23      0.374187E-1
_diffrn_orient_matrix_UB_31      0.130778E-1
_diffrn_orient_matrix_UB_32      -0.324834E-1
_diffrn_orient_matrix_UB_33      0.59382E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            38910
_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        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         2.44
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.386
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2168
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         7011
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0333P)²+5.6272P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0866
_reflns_number_gt                5746
_reflns_number_total             7011
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b414315a.txt
_cod_data_source_block           benzene-clathrate
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7216187
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_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C2 C 0.23075(4) 0.36036(12) 0.31790(8) 0.0166(2) Uani 1 1 d .
C3 C 0.26120(4) 0.41863(12) 0.36568(9) 0.0169(2) Uani 1 1 d .
H3 H 0.256 0.5052 0.3883 0.02 Uiso 1 1 calc R
C4 C 0.30122(4) 0.36644(12) 0.38736(8) 0.0166(2) Uani 1 1 d .
C5 C 0.30937(4) 0.23127(12) 0.41314(9) 0.0177(2) Uani 1 1 d .
C6 C 0.27893(4) 0.12788(12) 0.42330(9) 0.0179(2) Uani 1 1 d .
H6 H 0.2831 0.069 0.4745 0.021 Uiso 1 1 calc R
C7 C 0.24599(4) 0.10518(12) 0.37002(9) 0.0168(2) Uani 1 1 d .
C8 C 0.34831(4) 0.19605(13) 0.43762(9) 0.0204(2) Uani 1 1 d .
H8 H 0.3534 0.1082 0.4582 0.024 Uiso 1 1 calc R
C9 C 0.38069(4) 0.28529(13) 0.43318(9) 0.0202(2) Uani 1 1 d .
C10 C 0.42080(4) 0.24621(15) 0.45376(10) 0.0260(3) Uani 1 1 d .
H10 H 0.4266 0.1564 0.4681 0.031 Uiso 1 1 calc R
C11 C 0.45125(4) 0.33739(16) 0.45308(11) 0.0290(3) Uani 1 1 d .
H11 H 0.4779 0.3105 0.4674 0.035 Uiso 1 1 calc R
C12 C 0.44301(4) 0.47104(16) 0.43116(11) 0.0286(3) Uani 1 1 d .
H12 H 0.4643 0.5336 0.4312 0.034 Uiso 1 1 calc R
C13 C 0.40479(4) 0.51133(14) 0.40989(10) 0.0243(3) Uani 1 1 d .
H13 H 0.3997 0.6014 0.3948 0.029 Uiso 1 1 calc R
C14 C 0.37254(4) 0.41942(13) 0.41015(9) 0.0193(2) Uani 1 1 d .
C15 C 0.33255(4) 0.45708(13) 0.38986(9) 0.0187(2) Uani 1 1 d .
H15 H 0.3269 0.5475 0.3775 0.022 Uiso 1 1 calc R
C16 C 0.19144(4) 0.43246(12) 0.31019(9) 0.0182(2) Uani 1 1 d .
C17 C 0.16270(4) 0.40509(13) 0.23067(9) 0.0184(2) Uani 1 1 d .
C18 C 0.12227(4) 0.43450(14) 0.24436(10) 0.0231(3) Uani 1 1 d .
H18 H 0.114 0.467 0.3034 0.028 Uiso 1 1 calc R
C19 C 0.09418(4) 0.41654(15) 0.17229(10) 0.0253(3) Uani 1 1 d .
H19 H 0.0667 0.4356 0.1817 0.03 Uiso 1 1 calc R
C20 C 0.10698(4) 0.37039(13) 0.08665(10) 0.0225(3) Uani 1 1 d .
C21 C 0.14688(4) 0.34154(13) 0.07033(10) 0.0218(3) Uani 1 1 d .
H21 H 0.155 0.3108 0.0106 0.026 Uiso 1 1 calc R
C22 C 0.17470(4) 0.35859(13) 0.14327(9) 0.0189(2) Uani 1 1 d .
H22 H 0.2021 0.3384 0.1336 0.023 Uiso 1 1 calc R
C23 C 0.22071(4) -0.01419(12) 0.39188(9) 0.0176(2) Uani 1 1 d .
C24 C 0.17772(4) -0.02337(13) 0.36131(9) 0.0176(2) Uani 1 1 d .
C25 C 0.16215(4) -0.14967(13) 0.34351(9) 0.0218(3) Uani 1 1 d .
H25 H 0.1795 -0.2241 0.344 0.026 Uiso 1 1 calc R
C26 C 0.12156(4) -0.16679(14) 0.32513(10) 0.0254(3) Uani 1 1 d .
H26 H 0.1111 -0.2521 0.3113 0.03 Uiso 1 1 calc R
C27 C 0.09651(4) -0.05736(15) 0.32720(10) 0.0249(3) Uani 1 1 d .
C28 C 0.11119(4) 0.06880(15) 0.34258(10) 0.0246(3) Uani 1 1 d .
H28 H 0.0936 0.1428 0.3419 0.029 Uiso 1 1 calc R
C29 C 0.15214(4) 0.08560(13) 0.35908(9) 0.0210(3) Uani 1 1 d .
H29 H 0.1627 0.1719 0.3689 0.025 Uiso 1 1 calc R
Cl1 Cl 0.071611(11) 0.35041(4) -0.00404(3) 0.03514(10) Uani 1 1 d .
Cl2 Cl 0.044990(10) -0.07979(4) 0.31235(3) 0.03588(10) Uani 1 1 d .
O30 O 0.23572(3) -0.10572(10) 0.43632(7) 0.0249(2) Uani 1 1 d .
O31 O 0.18279(3) 0.51335(10) 0.37048(7) 0.0267(2) Uani 1 1 d .
S1 S 0.235269(9) 0.19974(3) 0.26769(2) 0.01762(7) Uani 1 1 d .
C32 C 0.00781(5) 0.30112(17) 0.29542(13) 0.0381(4) Uani 1 1 d .
H32 H 0.0132 0.2198 0.3265 0.046 Uiso 1 1 calc R
C33 C 0.01552(5) 0.41985(18) 0.34087(12) 0.0351(4) Uani 1 1 d .
H33 H 0.0261 0.42 0.4032 0.042 Uiso 1 1 calc R
C34 C 0.00779(5) 0.53807(17) 0.29535(12) 0.0336(3) Uani 1 1 d .
H34 H 0.0132 0.6195 0.3264 0.04 Uiso 1 1 calc R
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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C3 C2 C16 118.26(11) . .
C3 C2 S1 122.16(10) . .
C16 C2 S1 119.54(9) . .
C2 C3 C4 128.69(12) . .
C2 C3 H3 115.7 . .
C4 C3 H3 115.7 . .
C15 C4 C5 118.74(11) . .
C15 C4 C3 116.78(11) . .
C5 C4 C3 124.28(11) . .
C8 C5 C4 118.67(11) . .
C8 C5 C6 116.11(11) . .
C4 C5 C6 125.03(11) . .
C7 C6 C5 128.81(12) . .
C7 C6 H6 115.6 . .
C5 C6 H6 115.6 . .
C6 C7 C23 118.35(11) . .
C6 C7 S1 121.46(10) . .
C23 C7 S1 119.75(9) . .
C5 C8 C9 122.69(12) . .
C5 C8 H8 118.7 . .
C9 C8 H8 118.7 . .
C8 C9 C14 118.55(12) . .
C8 C9 C10 122.18(12) . .
C14 C9 C10 119.24(12) . .
C11 C10 C9 120.44(14) . .
C11 C10 H10 119.8 . .
C9 C10 H10 119.8 . .
C10 C11 C12 120.22(13) . .
C10 C11 H11 119.9 . .
C12 C11 H11 119.9 . .
C13 C12 C11 120.69(13) . .
C13 C12 H12 119.7 . .
C11 C12 H12 119.7 . .
C12 C13 C14 120.51(13) . .
C12 C13 H13 119.7 . .
C14 C13 H13 119.7 . .
C15 C14 C9 118.72(12) . .
C15 C14 C13 122.38(12) . .
C9 C14 C13 118.89(12) . .
C4 C15 C14 122.33(12) . .
C4 C15 H15 118.8 . .
C14 C15 H15 118.8 . .
O31 C16 C17 119.89(11) . .
O31 C16 C2 119.34(11) . .
C17 C16 C2 120.76(11) . .
C22 C17 C18 119.33(12) . .
C22 C17 C16 123.13(11) . .
C18 C17 C16 117.45(12) . .
C19 C18 C17 120.54(13) . .
C19 C18 H18 119.7 . .
C17 C18 H18 119.7 . .
C20 C19 C18 118.77(12) . .
C20 C19 H19 120.6 . .
C18 C19 H19 120.6 . .
C19 C20 C21 122.23(12) . .
C19 C20 Cl1 118.47(10) . .
C21 C20 Cl1 119.30(11) . .
C20 C21 C22 118.53(13) . .
C20 C21 H21 120.7 . .
C22 C21 H21 120.7 . .
C21 C22 C17 120.59(12) . .
C21 C22 H22 119.7 . .
C17 C22 H22 119.7 . .
O30 C23 C24 119.03(11) . .
O30 C23 C7 119.14(11) . .
C24 C23 C7 121.82(11) . .
C29 C24 C25 119.45(12) . .
C29 C24 C23 122.81(11) . .
C25 C24 C23 117.42(11) . .
C26 C25 C24 120.42(13) . .
C26 C25 H25 119.8 . .
C24 C25 H25 119.8 . .
C25 C26 C27 118.93(13) . .
C25 C26 H26 120.5 . .
C27 C26 H26 120.5 . .
C28 C27 C26 121.81(12) . .
C28 C27 Cl2 119.02(11) . .
C26 C27 Cl2 119.15(11) . .
C27 C28 C29 118.89(13) . .
C27 C28 H28 120.6 . .
C29 C28 H28 120.6 . .
C28 C29 C24 120.41(12) . .
C28 C29 H29 119.8 . .
C24 C29 H29 119.8 . .
C7 S1 C2 100.28(6) . .
C33 C32 C32 119.97(10) . 2
C33 C32 H32 120 . .
C32 C32 H32 120 2 .
C34 C33 C32 119.92(15) . .
C34 C33 H33 120 . .
C32 C33 H33 120 . .
C33 C34 C34 120.11(10) . 2
C33 C34 H34 119.9 . .
C34 C34 H34 119.9 2 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C2 C3 1.3478(17) .
C2 C16 1.5034(17) .
C2 S1 1.7823(13) .
C3 C4 1.4636(17) .
C3 H3 0.95 .
C4 C15 1.3905(17) .
C4 C5 1.4398(17) .
C5 C8 1.3859(17) .
C5 C6 1.4668(17) .
C6 C7 1.3438(17) .
C6 H6 0.95 .
C7 C23 1.5086(17) .
C7 S1 1.7743(13) .
C8 C9 1.4102(18) .
C8 H8 0.95 .
C9 C14 1.4204(18) .
C9 C10 1.4211(18) .
C10 C11 1.372(2) .
C10 H10 0.95 .
C11 C12 1.413(2) .
C11 H11 0.95 .
C12 C13 1.368(2) .
C12 H12 0.95 .
C13 C14 1.4222(18) .
C13 H13 0.95 .
C14 C15 1.4127(17) .
C15 H15 0.95 .
C16 O31 1.2247(16) .
C16 C17 1.4961(17) .
C17 C22 1.3971(18) .
C17 C18 1.3993(18) .
C18 C19 1.3889(19) .
C18 H18 0.95 .
C19 C20 1.382(2) .
C19 H19 0.95 .
C20 C21 1.3876(19) .
C20 Cl1 1.7450(13) .
C21 C22 1.3909(18) .
C21 H21 0.95 .
C22 H22 0.95 .
C23 O30 1.2233(16) .
C23 C24 1.4941(17) .
C24 C29 1.3941(18) .
C24 C25 1.4001(18) .
C25 C26 1.3859(19) .
C25 H25 0.95 .
C26 C27 1.388(2) .
C26 H26 0.95 .
C27 C28 1.383(2) .
C27 Cl2 1.7432(14) .
C28 C29 1.3927(18) .
C28 H28 0.95 .
C29 H29 0.95 .
C32 C33 1.386(3) .
C32 C32 1.386(4) 2
C32 H32 0.95 .
C33 C34 1.382(2) .
C33 H33 0.95 .
C34 C34 1.384(3) 2
C34 H34 0.95 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C16 C2 C3 C4 176.32(12) . .
S1 C2 C3 C4 -1.52(19) . .
C2 C3 C4 C15 146.16(13) . .
C2 C3 C4 C5 -39.0(2) . .
C15 C4 C5 C8 -1.32(18) . .
C3 C4 C5 C8 -176.07(12) . .
C15 C4 C5 C6 173.38(12) . .
C3 C4 C5 C6 -1.4(2) . .
C8 C5 C6 C7 -145.37(14) . .
C4 C5 C6 C7 39.8(2) . .
C5 C6 C7 C23 176.07(12) . .
C5 C6 C7 S1 3.72(19) . .
C4 C5 C8 C9 -3.72(19) . .
C6 C5 C8 C9 -178.88(12) . .
C5 C8 C9 C14 5.3(2) . .
C5 C8 C9 C10 -176.65(13) . .
C8 C9 C10 C11 -176.83(14) . .
C14 C9 C10 C11 1.2(2) . .
C9 C10 C11 C12 -0.5(2) . .
C10 C11 C12 C13 -0.3(2) . .
C11 C12 C13 C14 0.5(2) . .
C8 C9 C14 C15 -1.90(19) . .
C10 C9 C14 C15 -179.98(12) . .
C8 C9 C14 C13 177.05(12) . .
C10 C9 C14 C13 -1.02(19) . .
C12 C13 C14 C15 179.13(13) . .
C12 C13 C14 C9 0.2(2) . .
C5 C4 C15 C14 4.71(19) . .
C3 C4 C15 C14 179.85(12) . .
C9 C14 C15 C4 -3.08(19) . .
C13 C14 C15 C4 178.01(12) . .
C3 C2 C16 O31 -25.60(18) . .
S1 C2 C16 O31 152.30(11) . .
C3 C2 C16 C17 155.24(12) . .
S1 C2 C16 C17 -26.87(16) . .
O31 C16 C17 C22 154.12(13) . .
C2 C16 C17 C22 -26.72(18) . .
O31 C16 C17 C18 -22.53(18) . .
C2 C16 C17 C18 156.63(12) . .
C22 C17 C18 C19 0.6(2) . .
C16 C17 C18 C19 177.43(12) . .
C17 C18 C19 C20 -0.6(2) . .
C18 C19 C20 C21 0.0(2) . .
C18 C19 C20 Cl1 -179.08(11) . .
C19 C20 C21 C22 0.7(2) . .
Cl1 C20 C21 C22 179.72(10) . .
C20 C21 C22 C17 -0.67(19) . .
C18 C17 C22 C21 0.02(19) . .
C16 C17 C22 C21 -176.58(12) . .
C6 C7 C23 O30 -21.13(18) . .
S1 C7 C23 O30 151.36(10) . .
C6 C7 C23 C24 158.45(12) . .
S1 C7 C23 C24 -29.07(16) . .
O30 C23 C24 C29 143.61(13) . .
C7 C23 C24 C29 -35.97(18) . .
O30 C23 C24 C25 -29.89(18) . .
C7 C23 C24 C25 150.53(12) . .
C29 C24 C25 C26 -0.9(2) . .
C23 C24 C25 C26 172.79(12) . .
C24 C25 C26 C27 -1.7(2) . .
C25 C26 C27 C28 3.2(2) . .
C25 C26 C27 Cl2 -175.52(11) . .
C26 C27 C28 C29 -1.9(2) . .
Cl2 C27 C28 C29 176.83(11) . .
C27 C28 C29 C24 -0.9(2) . .
C25 C24 C29 C28 2.3(2) . .
C23 C24 C29 C28 -171.11(12) . .
C6 C7 S1 C2 -61.47(12) . .
C23 C7 S1 C2 126.28(10) . .
C3 C2 S1 C7 60.32(12) . .
C16 C2 S1 C7 -117.49(10) . .
C32 C32 C33 C34 -0.3(3) 2 .
C32 C33 C34 C34 0.3(3) . 2
loop_
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1 PubChem 139198632
