#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/13/4511315.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_4511315
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         'C22.50 H23 Cl N2 O2 S'
_chemical_formula_sum            'C22.5 H23 Cl N2 O2 S'
_chemical_formula_weight         420.94
_chemical_melting_point          432
_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                111.862(4)
_cell_angle_beta                 107.198(4)
_cell_angle_gamma                93.619(4)
_cell_formula_units_Z            2
_cell_length_a                   7.9174(18)
_cell_length_b                   11.701(3)
_cell_length_c                   13.248(3)
_cell_measurement_temperature    100(2)
_cell_volume                     1067.2(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      100(2)
_diffrn_measured_fraction_theta_full 0.931
_diffrn_measured_fraction_theta_max 0.931
_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  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0441
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12442
_diffrn_reflns_theta_full        28.39
_diffrn_reflns_theta_max         28.39
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_T_max  0.9567
_exptl_absorpt_correction_T_min  0.8511
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             442
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         4985
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0579
_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)+(0.0643P)²+0.8944P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1385
_refine_ls_wR_factor_ref         0.1462
_reflns_number_gt                4152
_reflns_number_total             4985
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            DiMe_DCM_an402_m.cif
_cod_data_source_block           an402_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_cell_volume        1067.1(4)
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C22.50 H23 Cl N2 O2 S'
_cod_database_code               4511315
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.87037(7) 0.33759(5) 1.02081(4) 0.02187(15) Uani 1 1 d . . .
O1 O 0.9860(2) 0.45665(14) 1.09987(12) 0.0268(3) Uani 1 1 d . . .
O2 O 0.7530(2) 0.27809(15) 1.05804(13) 0.0293(4) Uani 1 1 d . . .
N1 N 0.7431(2) 0.36692(18) 0.91353(16) 0.0263(4) Uani 1 1 d . . .
H1 H 0.800(4) 0.413(3) 0.898(2) 0.032(7) Uiso 1 1 d . . .
N2 N 0.6251(2) 0.26016(18) 0.82182(16) 0.0269(4) Uani 1 1 d . . .
C15 C 0.4150(3) 0.1621(2) 0.63089(18) 0.0228(4) Uani 1 1 d . . .
C8 C 0.5374(3) 0.2746(2) 0.73023(18) 0.0233(4) Uani 1 1 d . . .
C16 C 0.4234(3) 0.0419(2) 0.62811(19) 0.0259(5) Uani 1 1 d . . .
H16 H 0.5104 0.0315 0.6895 0.031 Uiso 1 1 calc R . .
C20 C 0.2876(3) 0.1734(2) 0.53831(18) 0.0242(4) Uani 1 1 d . . .
H20 H 0.2807 0.2541 0.5384 0.029 Uiso 1 1 calc R . .
C18 C 0.1773(3) -0.0511(2) 0.44366(18) 0.0241(4) Uani 1 1 d . . .
C19 C 0.1713(3) 0.0689(2) 0.44648(18) 0.0249(4) Uani 1 1 d . . .
H19 H 0.0860 0.0789 0.3843 0.030 Uiso 1 1 calc R . .
C5 C 1.0012(3) 0.2300(2) 0.96682(17) 0.0236(4) Uani 1 1 d . . .
C17 C 0.3057(3) -0.0616(2) 0.53640(19) 0.0266(5) Uani 1 1 d . . .
H17 H 0.3122 -0.1424 0.5364 0.032 Uiso 1 1 calc R . .
C9 C 0.5505(3) 0.3975(2) 0.72011(17) 0.0227(4) Uani 1 1 d . . .
C22 C 0.0517(3) -0.1649(2) 0.34281(19) 0.0310(5) Uani 1 1 d . . .
H22A H -0.0655 -0.1434 0.3142 0.047 Uiso 1 1 calc R . .
H22B H 0.0360 -0.2325 0.3680 0.047 Uiso 1 1 calc R . .
H22C H 0.1028 -0.1928 0.2807 0.047 Uiso 1 1 calc R . .
C4 C 0.9326(3) 0.1024(2) 0.9201(2) 0.0318(5) Uani 1 1 d . . .
H4 H 0.8145 0.0728 0.9149 0.038 Uiso 1 1 calc R . .
C3 C 1.0387(4) 0.0183(2) 0.8812(2) 0.0359(6) Uani 1 1 d . . .
H3 H 0.9917 -0.0693 0.8484 0.043 Uiso 1 1 calc R . .
C12 C 0.5769(3) 0.6299(2) 0.70448(19) 0.0278(5) Uani 1 1 d . . .
C2 C 1.2119(4) 0.0595(2) 0.8891(2) 0.0378(6) Uani 1 1 d . . .
C7 C 1.2761(4) 0.1871(3) 0.9337(3) 0.0463(7) Uani 1 1 d . . .
H7 H 1.3936 0.2166 0.9378 0.056 Uiso 1 1 calc R . .
C6 C 1.1719(3) 0.2731(2) 0.9725(2) 0.0345(5) Uani 1 1 d . . .
H6 H 1.2175 0.3607 1.0027 0.041 Uiso 1 1 calc R . .
C11 C 0.4865(5) 0.6051(3) 0.7689(3) 0.0609(10) Uani 1 1 d . . .
H11 H 0.4306 0.6676 0.8089 0.073 Uiso 1 1 calc R . .
C14 C 0.6396(4) 0.4213(2) 0.6541(3) 0.0464(7) Uani 1 1 d . . .
H14 H 0.6933 0.3582 0.6127 0.056 Uiso 1 1 calc R . .
C1 C 1.3270(5) -0.0339(3) 0.8489(3) 0.0580(9) Uani 1 1 d . . .
H2A H 1.2797 -0.0766 0.7642 0.087 Uiso 1 1 calc R . .
H2B H 1.3246 -0.0959 0.8821 0.087 Uiso 1 1 calc R . .
H2C H 1.4514 0.0104 0.8744 0.087 Uiso 1 1 calc R . .
C21 C 0.5942(4) 0.7562(2) 0.6986(3) 0.0441(7) Uani 1 1 d . . .
H21A H 0.4781 0.7636 0.6507 0.066 Uiso 1 1 calc R . .
H21B H 0.6859 0.7642 0.6643 0.066 Uiso 1 1 calc R . .
H21C H 0.6298 0.8228 0.7769 0.066 Uiso 1 1 calc R . .
C10 C 0.4740(5) 0.4909(3) 0.7777(3) 0.0608(10) Uani 1 1 d . . .
H10 H 0.4113 0.4770 0.8244 0.073 Uiso 1 1 calc R . .
C13 C 0.6528(4) 0.5364(3) 0.6465(3) 0.0525(8) Uani 1 1 d . . .
H13 H 0.7159 0.5508 0.6002 0.063 Uiso 1 1 calc R . .
C23 C 0.0682(8) 0.5101(6) 0.5995(6) 0.0552(16) Uani 0.50 1 d P . .
H23A H 0.1933 0.5013 0.6338 0.066 Uiso 0.50 1 calc PR A 1
H23B H 0.0076 0.5314 0.6578 0.066 Uiso 0.50 1 calc PR A 1
Cl1A Cl -0.0540(3) 0.3819(2) 0.47240(18) 0.0453(5) Uani 0.50 1 d P . 1
Cl1B Cl 0.0589(4) 0.6546(2) 0.5816(3) 0.0721(8) Uani 0.50 1 d P . 2
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_3
O2 S1 O1 119.60(10) .
O2 S1 N1 107.40(10) .
O1 S1 N1 103.80(10) .
O2 S1 C5 107.83(10) .
O1 S1 C5 109.34(10) .
N1 S1 C5 108.36(10) .
N2 N1 S1 113.51(14) .
C8 N2 N1 116.22(18) .
C20 C15 C16 118.3(2) .
C20 C15 C8 120.89(19) .
C16 C15 C8 120.81(18) .
N2 C8 C15 117.19(19) .
N2 C8 C9 123.6(2) .
C15 C8 C9 119.18(17) .
C17 C16 C15 120.11(19) .
C19 C20 C15 121.0(2) .
C19 C18 C17 117.5(2) .
C19 C18 C22 120.89(19) .
C17 C18 C22 121.6(2) .
C20 C19 C18 121.06(19) .
C6 C5 C4 120.4(2) .
C6 C5 S1 120.04(17) .
C4 C5 S1 119.51(17) .
C16 C17 C18 122.0(2) .
C14 C9 C10 117.6(2) .
C14 C9 C8 121.4(2) .
C10 C9 C8 121.0(2) .
C5 C4 C3 119.1(2) .
C2 C3 C4 121.3(2) .
C11 C12 C13 117.4(2) .
C11 C12 C21 120.9(2) .
C13 C12 C21 121.7(2) .
C7 C2 C3 118.5(2) .
C7 C2 C1 121.0(3) .
C3 C2 C1 120.5(3) .
C2 C7 C6 121.2(2) .
C5 C6 C7 119.3(2) .
C12 C11 C10 121.5(2) .
C9 C14 C13 120.9(2) .
C9 C10 C11 121.1(2) .
C12 C13 C14 121.5(2) .
Cl1A C23 Cl1B 111.7(3) .
Cl1A C23 Cl1A 93.4(3) 2_566
Cl1B C23 Cl1A 21.27(12) 2_566
C23 Cl1A C23 86.7(3) 2_566
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O2 1.4273(16) .
S1 O1 1.4358(16) .
S1 N1 1.6469(18) .
S1 C5 1.761(2) .
N1 N2 1.400(3) .
N2 C8 1.285(3) .
C15 C20 1.395(3) .
C15 C16 1.400(3) .
C15 C8 1.483(3) .
C8 C9 1.494(3) .
C16 C17 1.380(3) .
C20 C19 1.382(3) .
C18 C19 1.395(3) .
C18 C17 1.395(3) .
C18 C22 1.506(3) .
C5 C6 1.383(3) .
C5 C4 1.385(3) .
C9 C14 1.365(3) .
C9 C10 1.371(3) .
C4 C3 1.386(4) .
C3 C2 1.384(4) .
C12 C11 1.358(4) .
C12 C13 1.370(3) .
C12 C21 1.508(3) .
C2 C7 1.381(4) .
C2 C1 1.512(4) .
C7 C6 1.388(3) .
C11 C10 1.385(4) .
C14 C13 1.387(4) .
C23 Cl1A 1.730(7) .
C23 Cl1B 1.796(6) .
C23 Cl1A 1.835(7) 2_566
Cl1A C23 1.835(7) 2_566
