#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:19:41 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179660 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/13/4511311.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_4511311
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 Cl2 N2 O2 S, 0.5(C6 H6)'
_chemical_formula_sum            'C23 H19 Cl2 N2 O2 S'
_chemical_formula_weight         458.36
_chemical_melting_point          475
_chemical_name_systematic
; 
 ? 
;
_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                112.409(3)
_cell_angle_beta                 106.616(3)
_cell_angle_gamma                93.815(3)
_cell_formula_units_Z            2
_cell_length_a                   7.9816(16)
_cell_length_b                   11.793(2)
_cell_length_c                   13.501(3)
_cell_measurement_temperature    298(2)
_cell_volume                     1103.5(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0239
_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            11810
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.411
_exptl_absorpt_correction_T_max  0.902
_exptl_absorpt_correction_T_min  0.867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             474
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4464
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0630P)²+0.2343P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1164
_reflns_number_gt                3567
_reflns_number_total             4464
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            DiCl_Benzene_an516_m.cif
_cod_data_source_block           an516_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               4511311
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
S1 S 0.36313(6) 0.33728(5) 0.51708(4) 0.05285(15) Uani 1 1 d .
Cl2 Cl -0.43841(8) -0.17838(5) -0.16338(4) 0.06975(18) Uani 1 1 d .
Cl1 Cl 0.09511(10) 0.76852(6) 0.19372(7) 0.0900(2) Uani 1 1 d .
N2 N 0.1214(2) 0.26485(14) 0.32340(13) 0.0505(4) Uani 1 1 d .
C8 C 0.0381(2) 0.27986(17) 0.23395(15) 0.0467(4) Uani 1 1 d .
C18 C -0.3028(2) -0.04480(18) -0.04737(15) 0.0512(4) Uani 1 1 d .
O1 O 0.48140(19) 0.45412(13) 0.59548(11) 0.0647(4) Uani 1 1 d .
N1 N 0.2399(2) 0.36959(16) 0.41402(14) 0.0541(4) Uani 1 1 d .
C9 C 0.0541(2) 0.40175(16) 0.22434(15) 0.0462(4) Uani 1 1 d .
C15 C -0.0813(2) 0.16683(16) 0.13572(15) 0.0457(4) Uani 1 1 d .
O2 O 0.2437(2) 0.27968(15) 0.55257(12) 0.0675(4) Uani 1 1 d .
C5 C 0.4880(2) 0.22773(17) 0.46114(15) 0.0507(4) Uani 1 1 d .
C20 C -0.2020(2) 0.17569(18) 0.04295(16) 0.0543(4) Uani 1 1 d .
H20 H -0.2088 0.2540 0.0426 0.065 Uiso 1 1 calc R
C16 C -0.0741(3) 0.04861(18) 0.13392(16) 0.0541(4) Uani 1 1 d .
H16 H 0.0068 0.0407 0.1949 0.065 Uiso 1 1 calc R
C4 C 0.4195(3) 0.10134(19) 0.41764(18) 0.0616(5) Uani 1 1 d .
H4 H 0.3056 0.0738 0.4148 0.074 Uiso 1 1 calc R
C17 C -0.1846(3) -0.05704(18) 0.04362(16) 0.0561(5) Uani 1 1 d .
H17 H -0.1798 -0.1355 0.0439 0.067 Uiso 1 1 calc R
C11 C 0.0035(3) 0.61234(19) 0.28078(18) 0.0632(5) Uani 1 1 d .
H11 H -0.0395 0.6776 0.3247 0.076 Uiso 1 1 calc R
C19 C -0.3122(3) 0.07034(18) -0.04869(16) 0.0555(5) Uani 1 1 d .
H19 H -0.3918 0.0774 -0.1106 0.067 Uiso 1 1 calc R
C10 C -0.0088(3) 0.50001(19) 0.28972(17) 0.0577(5) Uani 1 1 d .
H10 H -0.0601 0.4897 0.3403 0.069 Uiso 1 1 calc R
C12 C 0.0796(3) 0.62677(17) 0.20662(17) 0.0571(5) Uani 1 1 d .
C14 C 0.1299(3) 0.41921(18) 0.14985(18) 0.0582(5) Uani 1 1 d .
H14 H 0.1725 0.3542 0.1053 0.070 Uiso 1 1 calc R
C2 C 0.6918(3) 0.0550(2) 0.38212(17) 0.0640(5) Uani 1 1 d .
C13 C 0.1431(3) 0.53180(19) 0.14062(19) 0.0633(5) Uani 1 1 d .
H13 H 0.1944 0.5431 0.0904 0.076 Uiso 1 1 calc R
C3 C 0.5218(3) 0.0164(2) 0.37853(19) 0.0680(6) Uani 1 1 d .
H3 H 0.4755 -0.0688 0.3491 0.082 Uiso 1 1 calc R
C6 C 0.6547(3) 0.2682(2) 0.46159(18) 0.0632(5) Uani 1 1 d .
H6 H 0.6990 0.3532 0.4880 0.076 Uiso 1 1 calc R
C7 C 0.7552(3) 0.1813(2) 0.42240(19) 0.0693(6) Uani 1 1 d .
H7 H 0.8678 0.2087 0.4233 0.083 Uiso 1 1 calc R
C1 C 0.8042(4) -0.0391(3) 0.3434(2) 0.0920(8) Uani 1 1 d .
H2A H 0.7569 -0.0841 0.2621 0.138 Uiso 1 1 calc R
H2B H 0.8028 -0.0968 0.3779 0.138 Uiso 1 1 calc R
H2C H 0.9246 0.0034 0.3657 0.138 Uiso 1 1 calc R
C22 C 0.4710(4) 0.3766(3) 0.9770(4) 0.1066(11) Uani 1 1 d .
H22 H 0.4511 0.2918 0.9609 0.128 Uiso 1 1 calc R
C21 C 0.5435(4) 0.4621(4) 1.0855(4) 0.1086(11) Uani 1 1 d .
H21 H 0.5732 0.4364 1.1443 0.130 Uiso 1 1 calc R
C23 C 0.4265(4) 0.4140(3) 0.8907(3) 0.1089(10) Uani 1 1 d .
H23 H 0.3759 0.3549 0.8157 0.131 Uiso 1 1 calc R
H1 H 0.300(3) 0.4153(19) 0.3992(17) 0.052(6) 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'
Cl Cl 0.1484 0.1585 '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
O2 S1 O1 119.93(9) . .
O2 S1 N1 106.93(9) . .
O1 S1 N1 103.69(9) . .
O2 S1 C5 108.01(9) . .
O1 S1 C5 109.21(9) . .
N1 S1 C5 108.55(9) . .
C8 N2 N1 116.45(15) . .
N2 C8 C15 116.32(15) . .
N2 C8 C9 124.23(16) . .
C15 C8 C9 119.45(15) . .
C19 C18 C17 121.14(17) . .
C19 C18 Cl2 119.60(14) . .
C17 C18 Cl2 119.24(15) . .
N2 N1 S1 113.22(12) . .
N2 N1 H1 117.8(15) . .
S1 N1 H1 111.3(14) . .
C14 C9 C10 118.50(17) . .
C14 C9 C8 121.09(16) . .
C10 C9 C8 120.41(16) . .
C20 C15 C16 118.13(16) . .
C20 C15 C8 121.26(16) . .
C16 C15 C8 120.61(16) . .
C4 C5 C6 120.16(19) . .
C4 C5 S1 119.85(15) . .
C6 C5 S1 119.99(15) . .
C19 C20 C15 121.18(17) . .
C19 C20 H20 119.4 . .
C15 C20 H20 119.4 . .
C17 C16 C15 121.26(17) . .
C17 C16 H16 119.4 . .
C15 C16 H16 119.4 . .
C3 C4 C5 119.3(2) . .
C3 C4 H4 120.3 . .
C5 C4 H4 120.3 . .
C16 C17 C18 119.07(17) . .
C16 C17 H17 120.5 . .
C18 C17 H17 120.5 . .
C12 C11 C10 119.13(18) . .
C12 C11 H11 120.4 . .
C10 C11 H11 120.4 . .
C18 C19 C20 119.22(17) . .
C18 C19 H19 120.4 . .
C20 C19 H19 120.4 . .
C11 C10 C9 120.95(19) . .
C11 C10 H10 119.5 . .
C9 C10 H10 119.5 . .
C11 C12 C13 121.55(18) . .
C11 C12 Cl1 119.67(16) . .
C13 C12 Cl1 118.77(17) . .
C13 C14 C9 120.88(18) . .
C13 C14 H14 119.6 . .
C9 C14 H14 119.6 . .
C7 C2 C3 118.3(2) . .
C7 C2 C1 121.2(2) . .
C3 C2 C1 120.6(2) . .
C12 C13 C14 118.98(19) . .
C12 C13 H13 120.5 . .
C14 C13 H13 120.5 . .
C4 C3 C2 121.4(2) . .
C4 C3 H3 119.3 . .
C2 C3 H3 119.3 . .
C5 C6 C7 119.4(2) . .
C5 C6 H6 120.3 . .
C7 C6 H6 120.3 . .
C2 C7 C6 121.3(2) . .
C2 C7 H7 119.4 . .
C6 C7 H7 119.4 . .
C2 C1 H2A 109.5 . .
C2 C1 H2B 109.5 . .
H2A C1 H2B 109.5 . .
C2 C1 H2C 109.5 . .
H2A C1 H2C 109.5 . .
H2B C1 H2C 109.5 . .
C21 C22 C23 120.0(3) . .
C21 C22 H22 120.0 . .
C23 C22 H22 120.0 . .
C22 C21 C23 120.2(3) . 2_667
C22 C21 H21 119.9 . .
C23 C21 H21 119.9 2_667 .
C21 C23 C22 119.8(3) 2_667 .
C21 C23 H23 120.1 2_667 .
C22 C23 H23 120.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O2 1.4222(15) .
S1 O1 1.4331(14) .
S1 N1 1.6491(16) .
S1 C5 1.758(2) .
Cl2 C18 1.7403(19) .
Cl1 C12 1.745(2) .
N2 C8 1.285(2) .
N2 N1 1.396(2) .
C8 C15 1.485(2) .
C8 C9 1.492(2) .
C18 C19 1.371(3) .
C18 C17 1.382(3) .
N1 H1 0.81(2) .
C9 C14 1.382(3) .
C9 C10 1.388(3) .
C15 C20 1.390(2) .
C15 C16 1.390(3) .
C5 C4 1.380(3) .
C5 C6 1.381(3) .
C20 C19 1.381(3) .
C20 H20 0.9300 .
C16 C17 1.377(3) .
C16 H16 0.9300 .
C4 C3 1.379(3) .
C4 H4 0.9300 .
C17 H17 0.9300 .
C11 C12 1.366(3) .
C11 C10 1.375(3) .
C11 H11 0.9300 .
C19 H19 0.9300 .
C10 H10 0.9300 .
C12 C13 1.371(3) .
C14 C13 1.380(3) .
C14 H14 0.9300 .
C2 C7 1.376(3) .
C2 C3 1.384(3) .
C2 C1 1.507(3) .
C13 H13 0.9300 .
C3 H3 0.9300 .
C6 C7 1.383(3) .
C6 H6 0.9300 .
C7 H7 0.9300 .
C1 H2A 0.9600 .
C1 H2B 0.9600 .
C1 H2C 0.9600 .
C22 C21 1.345(5) .
C22 C23 1.362(5) .
C22 H22 0.9300 .
C21 C23 1.359(5) 2_667
C21 H21 0.9300 .
C23 C21 1.359(5) 2_667
C23 H23 0.9300 .
