#------------------------------------------------------------------------------
#$Date: 2025-08-21 04:34:05 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301843 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/13/4511306.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_4511306
loop_
_publ_author_name
'Roy, Saikat'
'Nangia, Ashwini'
_publ_section_title
;
 Kinetic and Thermodynamic Conformational Polymorphs of Bis(p-tolyl)
 Ketonep-Tosylhydrazone:  The Curtin−Hammett Principle in
 Crystallization
;
_journal_issue                   10
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2047
_journal_paper_doi               10.1021/cg070542t
_journal_volume                  7
_journal_year                    2007
_chemical_formula_moiety         'C20 H16 Br2 N2 O2 S, 0.5(C6 H6)'
_chemical_formula_sum            'C23 H19 Br2 N2 O2 S'
_chemical_formula_weight         547.28
_chemical_melting_point          502
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                112.826(2)
_cell_angle_beta                 106.592(2)
_cell_angle_gamma                93.964(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0184(8)
_cell_length_b                   11.9872(12)
_cell_length_c                   13.5855(13)
_cell_measurement_temperature    298(2)
_cell_volume                     1129.26(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0378
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11845
_diffrn_reflns_theta_full        26.03
_diffrn_reflns_theta_max         26.03
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    3.704
_exptl_absorpt_correction_T_max  0.641
_exptl_absorpt_correction_T_min  0.434
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             546
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.624
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4429
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0497P)²+0.1195P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0998
_reflns_number_gt                3156
_reflns_number_total             4429
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            DiBr_benzene_an507_m.cif
_cod_data_source_block           an507_m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4511306
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Br1 Br 1.45114(5) 1.18687(3) 1.17218(3) 0.06351(14) Uani 1 1 d .
Br2 Br 0.90780(6) 0.23003(4) 0.80713(4) 0.08659(18) Uani 1 1 d .
S1 S 0.63749(11) 0.65891(8) 0.48052(7) 0.0538(2) Uani 1 1 d .
C8 C 0.9607(4) 0.7220(3) 0.7649(3) 0.0461(7) Uani 1 1 d .
N2 N 0.8776(3) 0.7355(2) 0.6754(2) 0.0498(6) Uani 1 1 d .
O2 O 0.7575(3) 0.7143(2) 0.44546(19) 0.0663(6) Uani 1 1 d .
C15 C 0.9449(4) 0.6025(3) 0.7748(2) 0.0460(7) Uani 1 1 d .
C12 C 1.3017(4) 1.0431(3) 1.0453(3) 0.0479(7) Uani 1 1 d .
N1 N 0.7594(4) 0.6309(3) 0.5856(2) 0.0546(7) Uani 1 1 d .
C14 C 1.1978(4) 0.8259(3) 0.9559(3) 0.0519(8) Uani 1 1 d .
H14 H 1.2020 0.7489 0.9566 0.062 Uiso 1 1 calc R
C11 C 1.1869(5) 1.0546(3) 0.9544(3) 0.0556(8) Uani 1 1 d .
H11 H 1.1842 1.1317 0.9538 0.067 Uiso 1 1 calc R
O1 O 0.5208(3) 0.5420(2) 0.40349(18) 0.0661(6) Uani 1 1 d .
C18 C 0.9235(4) 0.3819(3) 0.7937(3) 0.0539(8) Uani 1 1 d .
C19 C 1.0019(5) 0.3966(3) 0.7209(3) 0.0589(9) Uani 1 1 d .
H19 H 1.0477 0.3330 0.6786 0.071 Uiso 1 1 calc R
C5 C 0.5126(4) 0.7673(3) 0.5336(2) 0.0501(8) Uani 1 1 d .
C9 C 1.0800(4) 0.8343(3) 0.8629(3) 0.0450(7) Uani 1 1 d .
C13 C 1.3080(4) 0.9297(3) 1.0469(3) 0.0536(8) Uani 1 1 d .
H13 H 1.3861 0.9231 1.1089 0.064 Uiso 1 1 calc R
C10 C 1.0764(4) 0.9500(3) 0.8646(3) 0.0536(8) Uani 1 1 d .
H10 H 0.9972 0.9574 0.8034 0.064 Uiso 1 1 calc R
C20 C 1.0118(5) 0.5066(3) 0.7113(3) 0.0571(8) Uani 1 1 d .
H20 H 1.0639 0.5171 0.6616 0.069 Uiso 1 1 calc R
C2 C 0.3094(5) 0.9377(4) 0.6103(3) 0.0647(9) Uani 1 1 d .
C17 C 0.8566(5) 0.4745(3) 0.8573(3) 0.0601(9) Uani 1 1 d .
H17 H 0.8038 0.4630 0.9063 0.072 Uiso 1 1 calc R
C16 C 0.8682(5) 0.5851(3) 0.8479(3) 0.0566(8) Uani 1 1 d .
H16 H 0.8238 0.6487 0.8914 0.068 Uiso 1 1 calc R
C6 C 0.5811(5) 0.8922(3) 0.5773(3) 0.0614(9) Uani 1 1 d .
H6 H 0.6948 0.9197 0.5807 0.074 Uiso 1 1 calc R
C4 C 0.3433(4) 0.7276(3) 0.5301(3) 0.0614(9) Uani 1 1 d .
H4 H 0.2967 0.6436 0.5014 0.074 Uiso 1 1 calc R
C7 C 0.4790(5) 0.9752(3) 0.6156(3) 0.0679(10) Uani 1 1 d .
H7 H 0.5259 1.0593 0.6460 0.081 Uiso 1 1 calc R
C3 C 0.2452(5) 0.8140(4) 0.5694(3) 0.0709(10) Uani 1 1 d .
H3 H 0.1325 0.7874 0.5681 0.085 Uiso 1 1 calc R
C22 C 0.4542(6) 0.5322(7) 0.9116(6) 0.1088(18) Uani 1 1 d .
H22 H 0.4229 0.5540 0.8511 0.131 Uiso 1 1 calc R
C1 C 0.1993(6) 1.0322(4) 0.6509(4) 0.0953(14) Uani 1 1 d .
H2A H 0.0785 0.9910 0.6278 0.143 Uiso 1 1 calc R
H2B H 0.2032 1.0901 0.6183 0.143 Uiso 1 1 calc R
H2C H 0.2466 1.0754 0.7322 0.143 Uiso 1 1 calc R
C23 C 0.5244(6) 0.6205(5) 1.0188(7) 0.1070(19) Uani 1 1 d .
H23 H 0.5415 0.7033 1.0323 0.128 Uiso 1 1 calc R
C21 C 0.4293(6) 0.4112(6) 0.8920(5) 0.1093(17) Uani 1 1 d .
H21 H 0.3808 0.3500 0.8181 0.131 Uiso 1 1 calc R
H1 H 0.706(4) 0.582(3) 0.600(2) 0.038(9) Uiso 1 1 d .
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'
Br Br -0.2901 2.4595 '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_3
O2 S1 O1 120.27(15) .
O2 S1 N1 106.71(16) .
O1 S1 N1 103.50(15) .
O2 S1 C5 107.90(16) .
O1 S1 C5 109.46(15) .
N1 S1 C5 108.42(15) .
N2 C8 C9 116.4(3) .
N2 C8 C15 124.3(3) .
C9 C8 C15 119.4(3) .
C8 N2 N1 116.1(3) .
C16 C15 C20 118.6(3) .
C16 C15 C8 121.4(3) .
C20 C15 C8 120.0(3) .
C13 C12 C11 121.1(3) .
C13 C12 Br1 119.3(2) .
C11 C12 Br1 119.6(2) .
N2 N1 S1 113.6(2) .
C13 C14 C9 121.0(3) .
C10 C11 C12 118.8(3) .
C17 C18 C19 121.5(3) .
C17 C18 Br2 119.1(3) .
C19 C18 Br2 119.4(3) .
C18 C19 C20 119.0(3) .
C6 C5 C4 119.9(3) .
C6 C5 S1 120.1(3) .
C4 C5 S1 120.0(3) .
C10 C9 C14 118.1(3) .
C10 C9 C8 121.1(3) .
C14 C9 C8 120.8(3) .
C12 C13 C14 119.3(3) .
C11 C10 C9 121.6(3) .
C19 C20 C15 120.9(3) .
C3 C2 C7 118.2(4) .
C3 C2 C1 121.5(4) .
C7 C2 C1 120.4(4) .
C18 C17 C16 119.2(3) .
C15 C16 C17 120.8(3) .
C7 C6 C5 119.1(3) .
C3 C4 C5 119.2(3) .
C6 C7 C2 122.0(4) .
C2 C3 C4 121.6(4) .
C23 C22 C21 119.8(5) .
C22 C23 C21 120.3(5) 2_667
C22 C21 C23 119.9(6) 2_667
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C12 1.899(3) .
Br2 C18 1.899(3) .
S1 O2 1.419(2) .
S1 O1 1.434(2) .
S1 N1 1.651(3) .
S1 C5 1.754(3) .
C8 N2 1.286(4) .
C8 C9 1.485(4) .
C8 C15 1.489(4) .
N2 N1 1.396(4) .
C15 C16 1.378(4) .
C15 C20 1.391(4) .
C12 C13 1.373(4) .
C12 C11 1.375(4) .
C14 C13 1.374(4) .
C14 C9 1.389(4) .
C11 C10 1.374(4) .
C18 C17 1.367(5) .
C18 C19 1.371(5) .
C19 C20 1.374(5) .
C5 C6 1.380(5) .
C5 C4 1.388(4) .
C9 C10 1.381(4) .
C2 C3 1.365(5) .
C2 C7 1.376(5) .
C2 C1 1.516(5) .
C17 C16 1.380(4) .
C6 C7 1.373(5) .
C4 C3 1.379(5) .
C22 C23 1.346(8) .
C22 C21 1.358(7) .
C23 C21 1.367(7) 2_667
C21 C23 1.367(7) 2_667
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139147463
