# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_IPHAT-1
_database_code_depnum_ccdc_archive 'CCDC 1002352'
_audit_update_record             
;
2015-06-15 deposited with the CCDC.
2015-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 N4 O1 S, H2 O'
_chemical_formula_sum            'C19 H20 N4 O2 S'
_chemical_formula_weight         368.45
_chemical_absolute_configuration rm

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.450(5)
_cell_length_b                   4.956(5)
_cell_length_c                   26.730(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.301(5)
_cell_angle_gamma                90
_cell_volume                     1903(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5746
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      27.99

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.191
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9539
_exptl_absorpt_correction_T_max  0.9720
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            12965
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.836
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             3335
_reflns_number_gt                2409
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1124P)²+1.8061P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3335
_refine_ls_number_parameters     270
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0925
_refine_ls_R_factor_gt           0.0666
_refine_ls_wR_factor_ref         0.2181
_refine_ls_wR_factor_gt          0.1823
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3133(2) 0.0864(7) 0.15107(13) 0.0533(9) Uani 1 1 d . . . . .
C2 C 0.2984(2) 0.3067(8) 0.06787(13) 0.0559(9) Uani 1 1 d . . . . .
C3 C 0.3743(2) 0.3801(7) 0.10333(12) 0.0516(8) Uani 1 1 d . . . . .
C4 C 0.5594(2) 0.8369(8) 0.11298(14) 0.0620(10) Uani 1 1 d . . . . .
C5 C 0.5517(3) 0.9510(11) 0.06117(17) 0.0829(13) Uani 1 1 d . . . . .
H5A H 0.5597 0.8094 0.0375 0.124 Uiso 1 1 calc R U . . .
H5B H 0.5989 1.0855 0.0592 0.124 Uiso 1 1 calc R U . . .
H5C H 0.4914 1.0315 0.0534 0.124 Uiso 1 1 calc R U . . .
C6 C 0.6325(3) 0.9459(12) 0.1518(2) 0.0955(16) Uani 1 1 d . . . . .
H6A H 0.6280 0.8568 0.1834 0.143 Uiso 1 1 calc R U . . .
H6B H 0.6233 1.1362 0.1557 0.143 Uiso 1 1 calc R U . . .
H6C H 0.6930 0.9143 0.1413 0.143 Uiso 1 1 calc R U . . .
C7 C 0.2337(2) -0.2086(7) 0.20849(14) 0.0571(9) Uani 1 1 d . . . . .
C8 C 0.2174(3) -0.1998(10) 0.25856(17) 0.0793(13) Uani 1 1 d . . . . .
H8 H 0.2531 -0.0855 0.2805 0.095 Uiso 1 1 calc R U . . .
C9 C 0.1497(3) -0.3565(12) 0.2765(2) 0.0945(16) Uani 1 1 d . . . . .
H9 H 0.1395 -0.3480 0.3102 0.113 Uiso 1 1 calc R U . . .
C10 C 0.0975(3) -0.5253(11) 0.2440(2) 0.0899(16) Uani 1 1 d . . . . .
H10 H 0.0523 -0.6344 0.2558 0.108 Uiso 1 1 calc R U . . .
C11 C 0.1117(3) -0.5337(10) 0.1944(2) 0.0894(15) Uani 1 1 d . . . . .
H11 H 0.0750 -0.6464 0.1726 0.107 Uiso 1 1 calc R U . . .
C12 C 0.1806(3) -0.3757(8) 0.17578(17) 0.0692(11) Uani 1 1 d . . . . .
H12 H 0.1903 -0.3837 0.1420 0.083 Uiso 1 1 calc R U . . .
C13 C 0.2803(2) 0.4203(9) 0.01901(13) 0.0593(9) Uani 1 1 d . . . . .
C14 C 0.1970(3) 0.3450(9) -0.01666(14) 0.0649(10) Uani 1 1 d . . . . .
C17 C 0.0468(4) 0.2276(14) -0.0873(2) 0.118(2) Uani 1 1 d . . . . .
H17 H -0.0024 0.1768 -0.1107 0.142 Uiso 1 1 calc R U . A 1
S1 S 0.23522(6) 0.0577(2) 0.09660(3) 0.0593(4) Uani 1 1 d . . . . .
N1 N 0.38213(18) 0.2578(6) 0.14860(10) 0.0534(7) Uani 1 1 d . . . . .
N2 N 0.3061(2) -0.0447(7) 0.19418(12) 0.0616(8) Uani 1 1 d D . . . .
N3 N 0.43635(19) 0.5674(7) 0.09167(11) 0.0580(8) Uani 1 1 d D . . . .
N4 N 0.50610(19) 0.6543(7) 0.12790(11) 0.0577(8) Uani 1 1 d . . . . .
O1 O 0.3348(2) 0.5898(7) 0.00411(10) 0.0784(9) Uani 1 1 d . . . . .
C15 C 0.2034(5) 0.360(2) -0.0667(3) 0.091(3) Uani 0.620(7) 1 d . . P B 1
H15 H 0.2601 0.4078 -0.0777 0.109 Uiso 0.620(7) 1 calc R U P B 1
C16 C 0.1280(7) 0.308(2) -0.1021(3) 0.110(4) Uani 0.620(7) 1 d . . P B 1
H16 H 0.1339 0.3286 -0.1362 0.132 Uiso 0.620(7) 1 calc R U P B 1
C18 C 0.0379(6) 0.222(3) -0.0380(4) 0.173(8) Uani 0.620(7) 1 d . . P B 1
H18 H -0.0196 0.1783 -0.0275 0.208 Uiso 0.620(7) 1 calc R U P B 1
C19 C 0.1130(6) 0.280(3) -0.0015(3) 0.133(5) Uani 0.620(7) 1 d . . P B 1
H19 H 0.1054 0.2732 0.0326 0.160 Uiso 0.620(7) 1 calc R U P B 1
C15' C 0.1541(9) 0.550(3) -0.0476(5) 0.085(4) Uiso 0.380(7) 1 d . . P B 2
H15' H 0.1756 0.7266 -0.0445 0.102 Uiso 0.380(7) 1 calc R U P B 2
C16' C 0.0798(11) 0.486(4) -0.0829(6) 0.099(5) Uiso 0.380(7) 1 d . . P B 2
H16' H 0.0520 0.6196 -0.1038 0.119 Uiso 0.380(7) 1 calc R U P B 2
C18' C 0.0981(9) 0.019(3) -0.0603(5) 0.080(4) Uiso 0.380(7) 1 d . . P B 2
H18' H 0.0839 -0.1613 -0.0674 0.096 Uiso 0.380(7) 1 calc R U P B 2
C19' C 0.1676(8) 0.084(3) -0.0245(4) 0.072(3) Uiso 0.380(7) 1 d . . P B 2
H19' H 0.1964 -0.0524 -0.0045 0.087 Uiso 0.380(7) 1 calc R U P B 2
O1' O 0.46597(19) -0.0088(6) 0.26767(10) 0.0677(8) Uani 1 1 d D . . . .
H3 H 0.426(2) 0.649(6) 0.0572(6) 0.046(8) Uiso 1 1 d D . . . .
H2 H 0.3553(18) -0.002(8) 0.2225(9) 0.063(10) Uiso 1 1 d D . . . .
H1' H 0.486(3) -0.005(9) 0.3027(5) 0.081(13) Uiso 1 1 d D . . . .
H1'' H 0.496(4) -0.167(7) 0.257(2) 0.13(2) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.315(4) . ?
C1 N2 1.337(5) . ?
C1 S1 1.747(3) . ?
C2 C3 1.416(4) . ?
C2 C13 1.420(5) . ?
C2 S1 1.761(4) . ?
C3 N1 1.347(4) . ?
C3 N3 1.351(4) . ?
C4 N4 1.281(5) . ?
C4 C5 1.488(6) . ?
C4 C6 1.498(5) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C12 1.375(5) . ?
C7 C8 1.385(6) . ?
C7 N2 1.410(5) . ?
C8 C9 1.376(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.371(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.364(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.401(6) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 O1 1.246(5) . ?
C13 C14 1.499(5) . ?
C14 C15 1.353(8) . ?
C14 C19 1.359(9) . ?
C14 C19' 1.371(13) . ?
C14 C15' 1.410(14) . ?
C17 C18 1.337(12) . ?
C17 C16 1.341(11) . ?
C17 C16' 1.365(18) . ?
C17 C18' 1.422(14) . ?
C17 H17 0.9300 . ?
N2 H2 1.003(10) . ?
N3 N4 1.387(4) . ?
N3 H3 1.002(10) . ?
C15 C16 1.386(10) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C18 C19 1.407(11) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C15' C16' 1.39(2) . ?
C15' H15' 0.9300 . ?
C16' H16' 0.9300 . ?
C18' C19' 1.349(16) . ?
C18' H18' 0.9300 . ?
C19' H19' 0.9300 . ?
O1' H1' 0.950(10) . ?
O1' H1'' 0.954(10) . ?

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
_geom_angle_publ_flag
N1 C1 N2 119.2(3) . . ?
N1 C1 S1 115.7(3) . . ?
N2 C1 S1 125.1(3) . . ?
C3 C2 C13 124.4(3) . . ?
C3 C2 S1 106.8(3) . . ?
C13 C2 S1 128.8(3) . . ?
N1 C3 N3 121.6(3) . . ?
N1 C3 C2 117.9(3) . . ?
N3 C3 C2 120.5(3) . . ?
N4 C4 C5 124.9(3) . . ?
N4 C4 C6 116.2(4) . . ?
C5 C4 C6 118.9(4) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C7 C8 119.4(4) . . ?
C12 C7 N2 123.6(4) . . ?
C8 C7 N2 117.0(3) . . ?
C9 C8 C7 121.4(5) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C10 C9 C8 119.1(5) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C11 C10 C9 120.2(5) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 121.2(5) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C7 C12 C11 118.6(4) . . ?
C7 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
O1 C13 C2 120.1(3) . . ?
O1 C13 C14 117.2(3) . . ?
C2 C13 C14 122.8(4) . . ?
C15 C14 C19 117.9(5) . . ?
C19' C14 C15' 118.8(8) . . ?
C15 C14 C13 118.5(5) . . ?
C19 C14 C13 123.4(5) . . ?
C19' C14 C13 123.1(6) . . ?
C15' C14 C13 117.7(7) . . ?
C18 C17 C16 118.7(6) . . ?
C16' C17 C18' 118.7(10) . . ?
C18 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
C1 S1 C2 89.30(16) . . ?
C1 N1 C3 110.3(3) . . ?
C1 N2 C7 130.1(3) . . ?
C1 N2 H2 116(2) . . ?
C7 N2 H2 114(2) . . ?
C3 N3 N4 120.1(3) . . ?
C3 N3 H3 117.2(18) . . ?
N4 N3 H3 122.5(19) . . ?
C4 N4 N3 114.7(3) . . ?
C14 C15 C16 122.0(8) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
C17 C16 C15 120.0(7) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C17 C18 C19 121.9(8) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
C14 C19 C18 119.2(8) . . ?
C14 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C16' C15' C14 119.4(13) . . ?
C16' C15' H15' 120.3 . . ?
C14 C15' H15' 120.3 . . ?
C17 C16' C15' 120.7(14) . . ?
C17 C16' H16' 119.6 . . ?
C15' C16' H16' 119.6 . . ?
C19' C18' C17 119.4(12) . . ?
C19' C18' H18' 120.3 . . ?
C17 C18' H18' 120.3 . . ?
C18' C19' C14 121.9(11) . . ?
C18' C19' H19' 119.1 . . ?
C14 C19' H19' 119.1 . . ?
H1' O1' H1'' 102(4) . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 C2 C3 N1 179.1(4) . . . . ?
S1 C2 C3 N1 -0.7(4) . . . . ?
C13 C2 C3 N3 -0.8(6) . . . . ?
S1 C2 C3 N3 179.3(3) . . . . ?
C12 C7 C8 C9 0.5(6) . . . . ?
N2 C7 C8 C9 -178.6(4) . . . . ?
C7 C8 C9 C10 0.2(7) . . . . ?
C8 C9 C10 C11 -1.1(8) . . . . ?
C9 C10 C11 C12 1.3(7) . . . . ?
C8 C7 C12 C11 -0.3(6) . . . . ?
N2 C7 C12 C11 178.7(4) . . . . ?
C10 C11 C12 C7 -0.6(7) . . . . ?
C3 C2 C13 O1 2.7(6) . . . . ?
S1 C2 C13 O1 -177.5(3) . . . . ?
C3 C2 C13 C14 -177.5(4) . . . . ?
S1 C2 C13 C14 2.3(6) . . . . ?
O1 C13 C14 C15 28.6(7) . . . . ?
C2 C13 C14 C15 -151.2(6) . . . . ?
O1 C13 C14 C19 -146.6(8) . . . . ?
C2 C13 C14 C19 33.5(10) . . . . ?
O1 C13 C14 C19' 135.8(7) . . . . ?
C2 C13 C14 C19' -44.1(8) . . . . ?
O1 C13 C14 C15' -36.6(8) . . . . ?
C2 C13 C14 C15' 143.6(7) . . . . ?
N1 C1 S1 C2 -1.8(3) . . . . ?
N2 C1 S1 C2 176.2(4) . . . . ?
C3 C2 S1 C1 1.3(3) . . . . ?
C13 C2 S1 C1 -178.5(4) . . . . ?
N2 C1 N1 C3 -176.4(3) . . . . ?
S1 C1 N1 C3 1.7(4) . . . . ?
N3 C3 N1 C1 179.4(3) . . . . ?
C2 C3 N1 C1 -0.5(5) . . . . ?
N1 C1 N2 C7 170.8(4) . . . . ?
S1 C1 N2 C7 -7.1(6) . . . . ?
C12 C7 N2 C1 35.2(6) . . . . ?
C8 C7 N2 C1 -145.7(4) . . . . ?
N1 C3 N3 N4 -5.2(5) . . . . ?
C2 C3 N3 N4 174.7(3) . . . . ?
C5 C4 N4 N3 -1.0(6) . . . . ?
C6 C4 N4 N3 177.0(4) . . . . ?
C3 N3 N4 C4 -178.4(3) . . . . ?
C19 C14 C15 C16 -1.0(14) . . . . ?
C19' C14 C15 C16 56.7(11) . . . . ?
C15' C14 C15 C16 -70.5(11) . . . . ?
C13 C14 C15 C16 -176.6(8) . . . . ?
C18 C17 C16 C15 5.6(16) . . . . ?
C16' C17 C16 C15 74.3(13) . . . . ?
C18' C17 C16 C15 -54.1(12) . . . . ?
C14 C15 C16 C17 -3.0(16) . . . . ?
C16 C17 C18 C19 -4(2) . . . . ?
C16' C17 C18 C19 -54.9(17) . . . . ?
C18' C17 C18 C19 66.8(15) . . . . ?
C15 C14 C19 C18 2.2(17) . . . . ?
C19' C14 C19 C18 -68.9(14) . . . . ?
C15' C14 C19 C18 53.8(15) . . . . ?
C13 C14 C19 C18 177.6(11) . . . . ?
C17 C18 C19 C14 0(2) . . . . ?
C15 C14 C15' C16' 69.3(12) . . . . ?
C19 C14 C15' C16' -54.8(13) . . . . ?
C19' C14 C15' C16' 4.1(16) . . . . ?
C13 C14 C15' C16' 176.8(10) . . . . ?
C18 C17 C16' C15' 53.1(15) . . . . ?
C16 C17 C16' C15' -72.1(14) . . . . ?
C18' C17 C16' C15' -9(2) . . . . ?
C14 C15' C16' C17 1(2) . . . . ?
C18 C17 C18' C19' -64.0(12) . . . . ?
C16 C17 C18' C19' 59.6(12) . . . . ?
C16' C17 C18' C19' 12.0(17) . . . . ?
C17 C18' C19' C14 -7.0(18) . . . . ?
C15 C14 C19' C18' -50.5(12) . . . . ?
C19 C14 C19' C18' 72.7(12) . . . . ?
C15' C14 C19' C18' -1.1(15) . . . . ?
C13 C14 C19' C18' -173.3(9) . . . . ?

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_site_symmetry_A
N3 H3 O1 1.002(10) 1.85(2) 2.625(4) 131(2) .
N2 H2 O1' 1.003(10) 1.895(15) 2.869(4) 163(3) .
O1' H1' N4 0.950(10) 2.01(2) 2.892(4) 154(4) 2_645
O1' H1' N1 0.950(10) 2.48(3) 3.176(4) 130(3) 2_645
O1' H1'' O1' 0.954(10) 1.922(16) 2.864(4) 169(6) 2_645
C5 H5B O1 0.96 2.59 3.398(5) 141.5 3_675
C12 H12 S1 0.93 2.62 3.175(5) 119.1 .
N3 H3 O1 1.002(10) 1.85(2) 2.625(4) 131(2) .
N2 H2 O1' 1.003(10) 1.895(15) 2.869(4) 163(3) .
O1' H1' N1 0.950(10) 2.48(3) 3.176(4) 130(3) 2_645
O1' H1' N4 0.950(10) 2.01(2) 2.892(4) 154(4) 2_645
O1' H1'' O1' 0.954(10) 1.922(16) 2.864(4) 169(6) 2_645

_refine_diff_density_max         0.361
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.056

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol-Water (1:1)'
_chemical_properties_physical    Photo-sensitive
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1002353'
_audit_update_record             
;
2015-05-29 deposited with the CCDC.
2015-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
5-(4-chlorobenzoyl)-4-isopropylidenehydrazino-2-phenylaminothiazole
_chemical_name_common            'IPHAT 2'
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H19 Cl N4 O2 S'
_chemical_formula_sum            'C19 H19 Cl N4 O2 S'
_chemical_formula_weight         402.89

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.8580(5)
_cell_length_b                   4.85400(10)
_cell_length_c                   26.8190(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.2370(10)
_cell_angle_gamma                90
_cell_volume                     1934.19(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4038
_cell_measurement_theta_min      2.742
_cell_measurement_theta_max      25.309

_exptl_crystal_description       needles
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      1.385
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.328
_shelx_estimated_absorpt_T_min   0.908
_shelx_estimated_absorpt_T_max   0.937
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9010
_exptl_absorpt_correction_T_max  0.9632
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            13987
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.042
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             3394
_reflns_number_gt                2586
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0560P)²+1.1420P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3394
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1233
_refine_ls_wR_factor_gt          0.1098
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.31904(16) 0.8989(5) 0.83774(8) 0.0390(6) Uani 1 1 d . . . . .
C2 C 0.38254(16) 0.6047(5) 0.88824(9) 0.0402(6) Uani 1 1 d . . . . .
C3 C 0.31076(16) 0.6789(5) 0.91951(9) 0.0412(6) Uani 1 1 d . . . . .
C4 C 0.23605(16) 1.1952(5) 0.77721(9) 0.0417(6) Uani 1 1 d . . . . .
C5 C 0.18452(18) 1.3588(5) 0.80742(10) 0.0501(7) Uani 1 1 d . . . . .
H5 H 0.1963 1.3660 0.8415 0.060 Uiso 1 1 calc R U . . .
C6 C 0.1153(2) 1.5125(6) 0.78744(11) 0.0591(8) Uani 1 1 d . . . . .
H6 H 0.0801 1.6205 0.8083 0.071 Uiso 1 1 calc R U . . .
C7 C 0.0977(2) 1.5089(7) 0.73760(12) 0.0649(8) Uani 1 1 d . . . . .
H7 H 0.0511 1.6143 0.7244 0.078 Uiso 1 1 calc R U . . .
C8 C 0.1494(2) 1.3484(7) 0.70721(12) 0.0741(10) Uani 1 1 d . . . . .
H8 H 0.1379 1.3451 0.6731 0.089 Uiso 1 1 calc R U . . .
C9 C 0.2183(2) 1.1916(6) 0.72660(10) 0.0631(8) Uani 1 1 d . . . . .
H9 H 0.2531 1.0829 0.7056 0.076 Uiso 1 1 calc R U . . .
C10 C 0.56356(18) 0.1499(6) 0.88889(10) 0.0521(7) Uani 1 1 d . . . . .
C11 C 0.5565(2) 0.0335(7) 0.94023(11) 0.0706(9) Uani 1 1 d . . . . .
H11A H 0.5622 0.1793 0.9642 0.106 Uiso 1 1 calc R U . . .
H11B H 0.6036 -0.0988 0.9454 0.106 Uiso 1 1 calc R U . . .
H11C H 0.4991 -0.0547 0.9441 0.106 Uiso 1 1 calc R U . . .
C12 C 0.6348(2) 0.0399(8) 0.85539(13) 0.0853(11) Uani 1 1 d . . . . .
H12A H 0.6302 0.1269 0.8233 0.128 Uiso 1 1 calc R U . . .
H12B H 0.6272 -0.1554 0.8517 0.128 Uiso 1 1 calc R U . . .
H12C H 0.6929 0.0773 0.8696 0.128 Uiso 1 1 calc R U . . .
C13 C 0.29691(18) 0.5641(5) 0.96734(9) 0.0450(6) Uani 1 1 d . . . . .
C14 C 0.21867(17) 0.6347(5) 0.99932(8) 0.0413(6) Uani 1 1 d . . . . .
C17 C 0.0783(2) 0.7383(7) 1.06418(10) 0.0606(8) Uani 1 1 d . . . . .
C15 C 0.2297(4) 0.6241(12) 1.05017(18) 0.0484(15) Uani 0.509(4) 1 d . . P A 1
H15 H 0.2862 0.5861 1.0635 0.058 Uiso 0.509(4) 1 calc R U P A 1
C16 C 0.1581(4) 0.6689(14) 1.0818(2) 0.0544(16) Uani 0.509(4) 1 d . . P A 1
H16 H 0.1663 0.6498 1.1160 0.065 Uiso 0.509(4) 1 calc R U P A 1
C18 C 0.0612(4) 0.7147(13) 1.0120(2) 0.0591(17) Uani 0.509(4) 1 d . . P A 1
H18 H 0.0027 0.7248 0.9997 0.071 Uiso 0.509(4) 1 calc R U P A 1
C19 C 0.1328(4) 0.6767(12) 0.98028(19) 0.0503(15) Uani 0.509(4) 1 d . . P A 1
H19 H 0.1236 0.6792 0.9460 0.060 Uiso 0.509(4) 1 calc R U P A 1
C15' C 0.1881(4) 0.4431(15) 1.0338(2) 0.0607(18) Uani 0.491(4) 1 d . . P A 2
H15' H 0.2146 0.2698 1.0350 0.073 Uiso 0.491(4) 1 calc R U P A 2
C16' C 0.1194(5) 0.5034(18) 1.0664(2) 0.067(2) Uani 0.491(4) 1 d . . P A 2
H16' H 0.1024 0.3743 1.0902 0.081 Uiso 0.491(4) 1 calc R U P A 2
C18' C 0.1100(5) 0.9540(13) 1.0332(2) 0.0647(19) Uani 0.491(4) 1 d . . P A 2
H18' H 0.0857 1.1303 1.0350 0.078 Uiso 0.491(4) 1 calc R U P A 2
C19' C 0.1783(4) 0.8920(12) 1.0001(2) 0.0602(19) Uani 0.491(4) 1 d . . P A 2
H19' H 0.1976 1.0263 0.9778 0.072 Uiso 0.491(4) 1 calc R U P A 2
N1 N 0.30851(15) 1.0334(5) 0.79429(8) 0.0476(6) Uani 1 1 d . . . . .
N2 N 0.38740(13) 0.7282(4) 0.84319(7) 0.0415(5) Uani 1 1 d . . . . .
N3 N 0.44384(15) 0.4173(5) 0.90236(8) 0.0491(6) Uani 1 1 d . . . . .
N4 N 0.51118(14) 0.3329(4) 0.87096(8) 0.0460(5) Uani 1 1 d . . . . .
O2 O 0.53672(15) 0.5017(5) 0.76896(8) 0.0581(6) Uani 1 1 d . . . . .
O1 O 0.35146(14) 0.3933(4) 0.98463(7) 0.0655(6) Uani 1 1 d . . . . .
S1 S 0.24620(4) 0.92575(13) 0.88778(2) 0.0430(2) Uani 1 1 d . . . . .
Cl1 Cl -0.00991(6) 0.8065(3) 1.10439(3) 0.0995(4) Uani 1 1 d . . . . .
H1 H 0.3481(19) 1.001(6) 0.7738(10) 0.051(8) Uiso 1 1 d . . . . .
H3 H 0.4345(17) 0.350(5) 0.9312(10) 0.047(8) Uiso 1 1 d . . . . .
H2A H 0.511(3) 0.660(9) 0.7600(14) 0.096(14) Uiso 1 1 d . . . . .
H2B H 0.528(3) 0.472(8) 0.7976(14) 0.091(13) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.319(3) . ?
C1 N1 1.344(3) . ?
C1 S1 1.733(2) . ?
C2 N3 1.341(3) . ?
C2 N2 1.351(3) . ?
C2 C3 1.406(3) . ?
C3 C13 1.414(3) . ?
C3 S1 1.753(2) . ?
C4 C5 1.371(4) . ?
C4 C9 1.382(4) . ?
C4 N1 1.408(3) . ?
C5 C6 1.377(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.361(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.366(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.376(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 N4 1.274(3) . ?
C10 C12 1.490(4) . ?
C10 C11 1.493(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 O1 1.248(3) . ?
C13 C14 1.487(3) . ?
C14 C15 1.374(5) . ?
C14 C19' 1.386(6) . ?
C14 C19 1.387(6) . ?
C14 C15' 1.390(7) . ?
C17 C16' 1.295(8) . ?
C17 C16 1.318(7) . ?
C17 C18' 1.418(7) . ?
C17 C18 1.425(6) . ?
C17 Cl1 1.733(3) . ?
C15 C16 1.381(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C18 C19 1.379(7) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C15' C16' 1.377(9) . ?
C15' H15' 0.9300 . ?
C16' H16' 0.9300 . ?
C18' C19' 1.384(8) . ?
C18' H18' 0.9300 . ?
C19' H19' 0.9300 . ?
N1 H1 0.82(3) . ?
N3 N4 1.373(3) . ?
N3 H3 0.85(3) . ?
O2 H2A 0.89(4) . ?
O2 H2B 0.79(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
_geom_angle_publ_flag
N2 C1 N1 119.2(2) . . ?
N2 C1 S1 116.41(17) . . ?
N1 C1 S1 124.35(19) . . ?
N3 C2 N2 121.0(2) . . ?
N3 C2 C3 121.4(2) . . ?
N2 C2 C3 117.6(2) . . ?
C2 C3 C13 123.6(2) . . ?
C2 C3 S1 107.49(17) . . ?
C13 C3 S1 128.91(19) . . ?
C5 C4 C9 118.9(2) . . ?
C5 C4 N1 124.0(2) . . ?
C9 C4 N1 117.1(2) . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 121.0(3) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 119.2(3) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C7 C8 C9 120.6(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C4 120.2(3) . . ?
C8 C9 H9 119.9 . . ?
C4 C9 H9 119.9 . . ?
N4 C10 C12 117.2(3) . . ?
N4 C10 C11 124.5(2) . . ?
C12 C10 C11 118.2(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C13 C3 120.1(2) . . ?
O1 C13 C14 116.5(2) . . ?
C3 C13 C14 123.3(2) . . ?
C15 C14 C19 118.5(4) . . ?
C19' C14 C15' 116.8(4) . . ?
C15 C14 C13 118.3(3) . . ?
C19' C14 C13 123.7(3) . . ?
C19 C14 C13 122.8(3) . . ?
C15' C14 C13 119.2(3) . . ?
C16' C17 C18' 121.3(4) . . ?
C16 C17 C18 119.2(4) . . ?
C16' C17 Cl1 119.8(3) . . ?
C16 C17 Cl1 120.5(3) . . ?
C18' C17 Cl1 118.5(3) . . ?
C18 C17 Cl1 119.6(3) . . ?
C14 C15 C16 121.0(5) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C15 120.9(5) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C19 C18 C17 118.8(5) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
C18 C19 C14 120.2(5) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?
C16' C15' C14 121.7(6) . . ?
C16' C15' H15' 119.1 . . ?
C14 C15' H15' 119.1 . . ?
C17 C16' C15' 120.5(6) . . ?
C17 C16' H16' 119.7 . . ?
C15' C16' H16' 119.7 . . ?
C19' C18' C17 117.5(5) . . ?
C19' C18' H18' 121.3 . . ?
C17 C18' H18' 121.3 . . ?
C18' C19' C14 121.6(5) . . ?
C18' C19' H19' 119.2 . . ?
C14 C19' H19' 119.2 . . ?
C1 N1 C4 129.7(2) . . ?
C1 N1 H1 113.9(19) . . ?
C4 N1 H1 116.0(19) . . ?
C1 N2 C2 109.51(19) . . ?
C2 N3 N4 121.7(2) . . ?
C2 N3 H3 113.8(18) . . ?
N4 N3 H3 124.4(18) . . ?
C10 N4 N3 115.0(2) . . ?
H2A O2 H2B 110(4) . . ?
C1 S1 C3 88.98(11) . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 C2 C3 C13 -0.4(4) . . . . ?
N2 C2 C3 C13 179.3(2) . . . . ?
N3 C2 C3 S1 -179.8(2) . . . . ?
N2 C2 C3 S1 -0.1(3) . . . . ?
C9 C4 C5 C6 1.2(4) . . . . ?
N1 C4 C5 C6 179.4(2) . . . . ?
C4 C5 C6 C7 -1.1(4) . . . . ?
C5 C6 C7 C8 0.4(5) . . . . ?
C6 C7 C8 C9 0.1(5) . . . . ?
C7 C8 C9 C4 -0.1(5) . . . . ?
C5 C4 C9 C8 -0.6(4) . . . . ?
N1 C4 C9 C8 -178.9(3) . . . . ?
C2 C3 C13 O1 2.3(4) . . . . ?
S1 C3 C13 O1 -178.4(2) . . . . ?
C2 C3 C13 C14 -177.3(2) . . . . ?
S1 C3 C13 C14 2.0(4) . . . . ?
O1 C13 C14 C15 30.3(5) . . . . ?
C3 C13 C14 C15 -150.1(4) . . . . ?
O1 C13 C14 C19' 147.3(4) . . . . ?
C3 C13 C14 C19' -33.1(5) . . . . ?
O1 C13 C14 C19 -141.4(4) . . . . ?
C3 C13 C14 C19 38.2(5) . . . . ?
O1 C13 C14 C15' -26.8(5) . . . . ?
C3 C13 C14 C15' 152.8(4) . . . . ?
C19' C14 C15 C16 52.4(7) . . . . ?
C19 C14 C15 C16 -3.5(8) . . . . ?
C15' C14 C15 C16 -69.9(7) . . . . ?
C13 C14 C15 C16 -175.6(5) . . . . ?
C16' C17 C16 C15 78.0(7) . . . . ?
C18' C17 C16 C15 -49.6(7) . . . . ?
C18 C17 C16 C15 12.3(9) . . . . ?
Cl1 C17 C16 C15 -177.6(5) . . . . ?
C14 C15 C16 C17 -3.8(10) . . . . ?
C16' C17 C18 C19 -56.6(7) . . . . ?
C16 C17 C18 C19 -13.6(8) . . . . ?
C18' C17 C18 C19 67.2(6) . . . . ?
Cl1 C17 C18 C19 176.2(4) . . . . ?
C17 C18 C19 C14 6.4(8) . . . . ?
C15 C14 C19 C18 1.9(7) . . . . ?
C19' C14 C19 C18 -74.1(6) . . . . ?
C15' C14 C19 C18 46.2(6) . . . . ?
C13 C14 C19 C18 173.6(4) . . . . ?
C15 C14 C15' C16' 72.4(7) . . . . ?
C19' C14 C15' C16' 1.6(9) . . . . ?
C19 C14 C15' C16' -53.9(7) . . . . ?
C13 C14 C15' C16' 176.1(6) . . . . ?
C16 C17 C16' C15' -76.0(8) . . . . ?
C18' C17 C16' C15' -8.7(11) . . . . ?
C18 C17 C16' C15' 51.2(8) . . . . ?
Cl1 C17 C16' C15' 178.2(6) . . . . ?
C14 C15' C16' C17 3.2(12) . . . . ?
C16' C17 C18' C19' 9.1(9) . . . . ?
C16 C17 C18' C19' 52.9(7) . . . . ?
C18 C17 C18' C19' -67.1(6) . . . . ?
Cl1 C17 C18' C19' -177.7(5) . . . . ?
C17 C18' C19' C14 -4.1(9) . . . . ?
C15 C14 C19' C18' -47.0(7) . . . . ?
C19 C14 C19' C18' 74.2(7) . . . . ?
C15' C14 C19' C18' -0.9(8) . . . . ?
C13 C14 C19' C18' -175.1(5) . . . . ?
N2 C1 N1 C4 170.7(2) . . . . ?
S1 C1 N1 C4 -7.3(4) . . . . ?
C5 C4 N1 C1 34.5(4) . . . . ?
C9 C4 N1 C1 -147.2(3) . . . . ?
N1 C1 N2 C2 -176.7(2) . . . . ?
S1 C1 N2 C2 1.5(3) . . . . ?
N3 C2 N2 C1 178.8(2) . . . . ?
C3 C2 N2 C1 -0.9(3) . . . . ?
N2 C2 N3 N4 -3.3(4) . . . . ?
C3 C2 N3 N4 176.3(2) . . . . ?
C12 C10 N4 N3 176.8(3) . . . . ?
C11 C10 N4 N3 -1.3(4) . . . . ?
C2 N3 N4 C10 -178.7(3) . . . . ?
N2 C1 S1 C3 -1.4(2) . . . . ?
N1 C1 S1 C3 176.7(2) . . . . ?
C2 C3 S1 C1 0.78(19) . . . . ?
C13 C3 S1 C1 -178.6(3) . . . . ?

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_site_symmetry_A
N1 H1 O2 0.82(3) 2.06(3) 2.867(3) 166(3) 2_656
N3 H3 O1 0.85(3) 1.91(3) 2.606(3) 139(2) .
O2 H2B N4 0.79(4) 2.10(4) 2.882(3) 171(4) .

_refine_diff_density_max         0.491
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.045

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol-water (1:1)'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1052981'
_audit_update_record             
;
2015-05-29 deposited with the CCDC.
2015-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
4-benzylidenehydrazino-5-(4-chlorobenzoyl)-2-phenylaminothiazole
_chemical_name_common            BzHAT-MeOH
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H17 Cl N4 O S, C H4 O'
_chemical_formula_sum            'C24 H21 Cl N4 O2 S'
_chemical_formula_weight         464.96
_chemical_absolute_configuration rm

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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'

_cell_length_a                   9.6388(3)
_cell_length_b                   16.1889(4)
_cell_length_c                   14.8442(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.0760(10)
_cell_angle_gamma                90
_cell_volume                     2315.90(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9548
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      28.16

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      1.333
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.284
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9325
_exptl_absorpt_correction_T_max  0.9454
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            17752
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.498
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             4084
_reflns_number_gt                3506
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0457P)²+0.8861P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4084
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0980
_refine_ls_wR_factor_gt          0.0899
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3351(2) 0.12002(13) 0.41581(13) 0.0561(5) Uani 1 1 d . . . . .
C2 C 0.3902(2) 0.04495(13) 0.39237(13) 0.0579(5) Uani 1 1 d . . . . .
H2 H 0.3761 -0.0013 0.4282 0.069 Uiso 1 1 calc R U . . .
C3 C 0.4667(2) 0.03912(11) 0.31486(13) 0.0521(4) Uani 1 1 d . . . . .
H3 H 0.5027 -0.0117 0.2979 0.062 Uiso 1 1 calc R U . . .
C4 C 0.49061(17) 0.10826(11) 0.26202(12) 0.0440(4) Uani 1 1 d . . . . .
C5 C 0.4359(2) 0.18345(12) 0.28822(13) 0.0540(5) Uani 1 1 d . . . . .
H5 H 0.4525 0.2304 0.2539 0.065 Uiso 1 1 calc R U . . .
C6 C 0.3568(2) 0.18955(13) 0.36482(14) 0.0599(5) Uani 1 1 d . . . . .
H6 H 0.3188 0.2400 0.3815 0.072 Uiso 1 1 calc R U . . .
C7 C 0.57244(18) 0.09847(10) 0.17833(12) 0.0439(4) Uani 1 1 d . . . . .
C8 C 0.68294(18) 0.15224(10) 0.16052(11) 0.0420(4) Uani 1 1 d . . . . .
C9 C 0.77911(18) 0.14228(10) 0.09099(11) 0.0412(4) Uani 1 1 d . . . . .
C10 C 0.89136(18) 0.23856(10) 0.16448(11) 0.0411(4) Uani 1 1 d . . . . .
C11 C 1.11097(17) 0.31258(10) 0.13700(11) 0.0413(4) Uani 1 1 d . . . . .
C12 C 1.11592(19) 0.30367(12) 0.04434(12) 0.0516(4) Uani 1 1 d . . . . .
H12 H 1.0422 0.2795 0.0128 0.062 Uiso 1 1 calc R U . . .
C13 C 1.2311(2) 0.33089(13) -0.00084(13) 0.0594(5) Uani 1 1 d . . . . .
H13 H 1.2333 0.3260 -0.0632 0.071 Uiso 1 1 calc R U . . .
C14 C 1.3420(2) 0.36489(13) 0.04440(15) 0.0614(5) Uani 1 1 d . . . . .
H14 H 1.4195 0.3824 0.0132 0.074 Uiso 1 1 calc R U . . .
C15 C 1.3377(2) 0.37285(13) 0.13632(15) 0.0587(5) Uani 1 1 d . . . . .
H15 H 1.4131 0.3955 0.1676 0.070 Uiso 1 1 calc R U . . .
C16 C 1.22244(19) 0.34746(11) 0.18290(12) 0.0499(4) Uani 1 1 d . . . . .
H16 H 1.2199 0.3539 0.2451 0.060 Uiso 1 1 calc R U . . .
C17 C 0.84109(19) 0.01718(11) -0.09417(11) 0.0471(4) Uani 1 1 d . . . . .
H17 H 0.7641 -0.0170 -0.0887 0.057 Uiso 1 1 calc R U . . .
C18 C 0.93937(18) 0.00240(11) -0.16610(11) 0.0441(4) Uani 1 1 d . . . . .
C19 C 0.9131(2) -0.05961(12) -0.22852(12) 0.0522(4) Uani 1 1 d . . . . .
H19 H 0.8341 -0.0922 -0.2236 0.063 Uiso 1 1 calc R U . . .
C20 C 1.0039(2) -0.07342(13) -0.29829(13) 0.0592(5) Uani 1 1 d . . . . .
H20 H 0.9854 -0.1151 -0.3399 0.071 Uiso 1 1 calc R U . . .
C21 C 1.1210(2) -0.02576(13) -0.30609(14) 0.0607(5) Uani 1 1 d . . . . .
H21 H 1.1814 -0.0349 -0.3532 0.073 Uiso 1 1 calc R U . . .
C22 C 1.1485(2) 0.03558(13) -0.24390(14) 0.0586(5) Uani 1 1 d . . . . .
H22 H 1.2282 0.0675 -0.2488 0.070 Uiso 1 1 calc R U . . .
C23 C 1.05877(19) 0.04991(12) -0.17450(13) 0.0515(4) Uani 1 1 d . . . . .
H23 H 1.0781 0.0916 -0.1330 0.062 Uiso 1 1 calc R U . . .
N1 N 0.89330(14) 0.19085(8) 0.09318(9) 0.0421(3) Uani 1 1 d . . . . .
N2 N 0.99265(15) 0.29177(9) 0.18764(9) 0.0472(4) Uani 1 1 d . . . . .
H2A H 0.9850 0.3159 0.2389 0.057 Uiso 1 1 calc R U . . .
N3 N 0.76209(15) 0.08526(9) 0.02587(9) 0.0474(4) Uani 1 1 d . . . . .
H3A H 0.6895 0.0543 0.0250 0.057 Uiso 1 1 calc R U . . .
N4 N 0.85992(15) 0.07629(9) -0.03901(9) 0.0455(3) Uani 1 1 d . . . . .
O1 O 0.54276(14) 0.03937(8) 0.12542(9) 0.0550(3) Uani 1 1 d . . . . .
S1 S 0.74584(5) 0.23060(3) 0.23226(3) 0.04583(14) Uani 1 1 d . . . . .
Cl1 Cl 0.23602(7) 0.12677(5) 0.51230(4) 0.0860(2) Uani 1 1 d . . . . .
O1' O 0.5131(2) -0.12662(9) 0.14531(10) 0.0855(6) Uani 1 1 d . . . . .
H1' H 0.5191 -0.0763 0.1406 0.128 Uiso 1 1 calc R U . . .
C1' C 0.5613(4) -0.16314(19) 0.06872(17) 0.1023(10) Uani 1 1 d . . . . .
H1'1 H 0.5298 -0.1324 0.0170 0.153 Uiso 1 1 calc R U . . .
H1'2 H 0.5271 -0.2187 0.0648 0.153 Uiso 1 1 calc R U . . .
H1'3 H 0.6609 -0.1639 0.0708 0.153 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.373(3) . ?
C1 C6 1.375(3) . ?
C1 Cl1 1.7399(18) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.389(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(3) . ?
C4 C7 1.492(2) . ?
C5 C6 1.384(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.267(2) . ?
C7 C8 1.405(2) . ?
C8 C9 1.409(2) . ?
C8 S1 1.7567(17) . ?
C9 N3 1.344(2) . ?
C9 N1 1.353(2) . ?
C10 N1 1.311(2) . ?
C10 N2 1.342(2) . ?
C10 S1 1.7463(16) . ?
C11 C16 1.382(2) . ?
C11 C12 1.385(2) . ?
C11 N2 1.418(2) . ?
C12 C13 1.380(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.368(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.382(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 N4 1.270(2) . ?
C17 C18 1.460(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.386(2) . ?
C18 C23 1.392(3) . ?
C19 C20 1.386(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.374(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.378(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.377(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
N2 H2A 0.8600 . ?
N3 N4 1.3681(19) . ?
N3 H3A 0.8600 . ?
O1' C1' 1.370(3) . ?
O1' H1' 0.8200 . ?
C1' H1'1 0.9600 . ?
C1' H1'2 0.9600 . ?
C1' H1'3 0.9600 . ?

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
_geom_angle_publ_flag
C2 C1 C6 121.45(17) . . ?
C2 C1 Cl1 119.00(16) . . ?
C6 C1 Cl1 119.55(16) . . ?
C1 C2 C3 119.10(18) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C4 120.81(18) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 118.79(16) . . ?
C5 C4 C7 122.48(16) . . ?
C3 C4 C7 118.72(16) . . ?
C6 C5 C4 120.79(18) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C1 C6 C5 119.04(19) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
O1 C7 C8 120.96(15) . . ?
O1 C7 C4 118.65(15) . . ?
C8 C7 C4 120.35(15) . . ?
C7 C8 C9 125.34(15) . . ?
C7 C8 S1 125.99(13) . . ?
C9 C8 S1 107.60(12) . . ?
N3 C9 N1 120.31(15) . . ?
N3 C9 C8 122.15(15) . . ?
N1 C9 C8 117.51(15) . . ?
N1 C10 N2 124.32(15) . . ?
N1 C10 S1 116.46(13) . . ?
N2 C10 S1 119.22(12) . . ?
C16 C11 C12 119.43(16) . . ?
C16 C11 N2 117.46(15) . . ?
C12 C11 N2 123.01(16) . . ?
C13 C12 C11 119.51(18) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C14 C13 C12 121.23(19) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 119.24(18) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C14 C15 C16 120.60(18) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C11 C16 C15 119.98(17) . . ?
C11 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
N4 C17 C18 120.53(16) . . ?
N4 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C23 118.76(17) . . ?
C19 C18 C17 119.65(17) . . ?
C23 C18 C17 121.59(16) . . ?
C18 C19 C20 120.42(19) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C21 C20 C19 120.22(18) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 119.77(18) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C23 C22 C21 120.43(19) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C18 120.39(18) . . ?
C22 C23 H23 119.8 . . ?
C18 C23 H23 119.8 . . ?
C10 N1 C9 109.76(14) . . ?
C10 N2 C11 127.23(14) . . ?
C10 N2 H2A 116.4 . . ?
C11 N2 H2A 116.4 . . ?
C9 N3 N4 120.18(14) . . ?
C9 N3 H3A 119.9 . . ?
N4 N3 H3A 119.9 . . ?
C17 N4 N3 116.22(15) . . ?
C10 S1 C8 88.62(8) . . ?
C1' O1' H1' 109.5 . . ?
O1' C1' H1'1 109.5 . . ?
O1' C1' H1'2 109.5 . . ?
H1'1 C1' H1'2 109.5 . . ?
O1' C1' H1'3 109.5 . . ?
H1'1 C1' H1'3 109.5 . . ?
H1'2 C1' H1'3 109.5 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.2(3) . . . . ?
Cl1 C1 C2 C3 178.81(15) . . . . ?
C1 C2 C3 C4 1.3(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C2 C3 C4 C7 -179.23(17) . . . . ?
C3 C4 C5 C6 -1.1(3) . . . . ?
C7 C4 C5 C6 177.93(18) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
Cl1 C1 C6 C5 179.95(15) . . . . ?
C4 C5 C6 C1 1.2(3) . . . . ?
C5 C4 C7 O1 -132.20(19) . . . . ?
C3 C4 C7 O1 46.8(2) . . . . ?
C5 C4 C7 C8 49.9(3) . . . . ?
C3 C4 C7 C8 -131.10(19) . . . . ?
O1 C7 C8 C9 -7.2(3) . . . . ?
C4 C7 C8 C9 170.65(16) . . . . ?
O1 C7 C8 S1 -173.90(14) . . . . ?
C4 C7 C8 S1 4.0(2) . . . . ?
C7 C8 C9 N3 9.8(3) . . . . ?
S1 C8 C9 N3 178.48(14) . . . . ?
C7 C8 C9 N1 -168.21(16) . . . . ?
S1 C8 C9 N1 0.51(19) . . . . ?
C16 C11 C12 C13 -1.0(3) . . . . ?
N2 C11 C12 C13 175.31(18) . . . . ?
C11 C12 C13 C14 1.5(3) . . . . ?
C12 C13 C14 C15 -0.8(3) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C12 C11 C16 C15 -0.2(3) . . . . ?
N2 C11 C16 C15 -176.71(17) . . . . ?
C14 C15 C16 C11 1.0(3) . . . . ?
N4 C17 C18 C19 -176.55(17) . . . . ?
N4 C17 C18 C23 2.6(3) . . . . ?
C23 C18 C19 C20 -0.5(3) . . . . ?
C17 C18 C19 C20 178.71(17) . . . . ?
C18 C19 C20 C21 0.1(3) . . . . ?
C19 C20 C21 C22 0.4(3) . . . . ?
C20 C21 C22 C23 -0.6(3) . . . . ?
C21 C22 C23 C18 0.2(3) . . . . ?
C19 C18 C23 C22 0.3(3) . . . . ?
C17 C18 C23 C22 -178.87(17) . . . . ?
N2 C10 N1 C9 177.48(16) . . . . ?
S1 C10 N1 C9 -2.45(18) . . . . ?
N3 C9 N1 C10 -176.82(15) . . . . ?
C8 C9 N1 C10 1.2(2) . . . . ?
N1 C10 N2 C11 6.7(3) . . . . ?
S1 C10 N2 C11 -173.33(13) . . . . ?
C16 C11 N2 C10 -160.20(17) . . . . ?
C12 C11 N2 C10 23.4(3) . . . . ?
N1 C9 N3 N4 -0.4(2) . . . . ?
C8 C9 N3 N4 -178.29(15) . . . . ?
C18 C17 N4 N3 179.86(15) . . . . ?
C9 N3 N4 C17 175.08(16) . . . . ?
N1 C10 S1 C8 2.37(14) . . . . ?
N2 C10 S1 C8 -177.56(15) . . . . ?
C7 C8 S1 C10 167.15(16) . . . . ?
C9 C8 S1 C10 -1.48(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_site_symmetry_A
C12 H12 N1 0.93 2.37 2.920(2) 117.8 .
N2 H2A O1' 0.86 1.95 2.811(2) 174.4 2_655
N3 H3A O1 0.86 2.09 2.7060(18) 128.2 .
O1' H1' O1 0.82 1.90 2.719(2) 176.4 .

_refine_diff_density_max         0.256
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.036

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol-water (1:1)'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1052982'
_audit_update_record             
;
2015-05-29 deposited with the CCDC.
2015-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
4-benzylidenehydrazino-5-(4-chlorobenzoyl)-2-phenylaminothiazole
_chemical_name_common            BzHAT-EtOH
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H17 Cl N4 O S, C2 H6 O'
_chemical_formula_sum            'C25 H23 Cl N4 O2 S'
_chemical_formula_weight         478.98
_chemical_absolute_configuration rm

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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'

_cell_length_a                   9.6720(2)
_cell_length_b                   16.4163(3)
_cell_length_c                   15.2160(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.8050(10)
_cell_angle_gamma                90
_cell_volume                     2415.73(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7789
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      27.27

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      1.316
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.274
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9346
_exptl_absorpt_correction_T_max  0.9600
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            20680
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.444
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5259
_reflns_number_gt                3971
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0568P)²+0.9068P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5259
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1296
_refine_ls_wR_factor_gt          0.1136
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1996(2) 0.14634(11) 0.33614(12) 0.0499(4) Uani 1 1 d . . . . .
C2 C 0.4006(2) 0.23679(11) 0.33823(12) 0.0484(4) Uani 1 1 d . . . . .
C3 C 0.2954(2) 0.13888(11) 0.40654(12) 0.0476(4) Uani 1 1 d . . . . .
C4 C 0.0898(2) 0.09224(12) 0.31765(13) 0.0523(5) Uani 1 1 d . . . . .
C5 C 0.0018(2) 0.10446(12) 0.23722(13) 0.0528(5) Uani 1 1 d . . . . .
C6 C -0.0279(2) 0.03803(13) 0.18386(15) 0.0625(5) Uani 1 1 d . . . . .
H6 H 0.0074 -0.0129 0.1987 0.075 Uiso 1 1 calc R U . . .
C7 C -0.1090(3) 0.04639(16) 0.10924(15) 0.0708(6) Uani 1 1 d . . . . .
H7 H -0.1269 0.0018 0.0732 0.085 Uiso 1 1 calc R U . . .
C8 C -0.1630(2) 0.12147(16) 0.08884(15) 0.0655(6) Uani 1 1 d . . . . .
C9 C -0.1364(2) 0.18865(16) 0.14045(17) 0.0709(6) Uani 1 1 d . . . . .
H9 H -0.1734 0.2392 0.1257 0.085 Uiso 1 1 calc R U . . .
C10 C -0.0535(2) 0.17949(14) 0.21483(15) 0.0649(6) Uani 1 1 d . . . . .
H10 H -0.0347 0.2245 0.2502 0.078 Uiso 1 1 calc R U . . .
C11 C 0.6137(2) 0.31503(11) 0.36916(12) 0.0477(4) Uani 1 1 d . . . . .
C12 C 0.7267(2) 0.34636(13) 0.32574(14) 0.0588(5) Uani 1 1 d . . . . .
H12 H 0.7262 0.3489 0.2647 0.071 Uiso 1 1 calc R U . . .
C13 C 0.8399(2) 0.37387(15) 0.37300(17) 0.0678(6) Uani 1 1 d . . . . .
H13 H 0.9163 0.3940 0.3435 0.081 Uiso 1 1 calc R U . . .
C14 C 0.8411(2) 0.37184(14) 0.46315(16) 0.0665(6) Uani 1 1 d . . . . .
H14 H 0.9171 0.3912 0.4948 0.080 Uiso 1 1 calc R U . . .
C15 C 0.7291(2) 0.34101(14) 0.50599(15) 0.0645(6) Uani 1 1 d . . . . .
H15 H 0.7296 0.3397 0.5671 0.077 Uiso 1 1 calc R U . . .
C16 C 0.6155(2) 0.31182(13) 0.46013(13) 0.0566(5) Uani 1 1 d . . . . .
H16 H 0.5407 0.2902 0.4900 0.068 Uiso 1 1 calc R U . . .
C17 C 0.3513(2) 0.02130(13) 0.59408(13) 0.0580(5) Uani 1 1 d . . . . .
H17 H 0.2744 -0.0123 0.5870 0.070 Uiso 1 1 calc R U . . .
C18 C 0.4446(2) 0.00876(12) 0.66903(12) 0.0515(5) Uani 1 1 d . . . . .
C19 C 0.4175(2) -0.05318(13) 0.72855(14) 0.0606(5) Uani 1 1 d . . . . .
H19 H 0.3402 -0.0862 0.7204 0.073 Uiso 1 1 calc R U . . .
C20 C 0.5053(3) -0.06604(14) 0.79997(15) 0.0684(6) Uani 1 1 d . . . . .
H20 H 0.4866 -0.1077 0.8395 0.082 Uiso 1 1 calc R U . . .
C21 C 0.6193(2) -0.01777(15) 0.81256(16) 0.0669(6) Uani 1 1 d . . . . .
H21 H 0.6780 -0.0266 0.8606 0.080 Uiso 1 1 calc R U . . .
C22 C 0.6469(2) 0.04378(15) 0.75414(16) 0.0650(6) Uani 1 1 d . . . . .
H22 H 0.7244 0.0765 0.7628 0.078 Uiso 1 1 calc R U . . .
C23 C 0.5604(2) 0.05740(13) 0.68266(14) 0.0571(5) Uani 1 1 d . . . . .
H23 H 0.5797 0.0993 0.6435 0.069 Uiso 1 1 calc R U . . .
C24 C -0.0211(4) 0.1764(2) 0.5770(2) 0.1031(10) Uani 1 1 d . . . . .
H24A H 0.0725 0.1735 0.5552 0.124 Uiso 1 1 calc R U . . .
H24B H -0.0410 0.2332 0.5893 0.124 Uiso 1 1 calc R U . . .
O2 O -0.0280(3) 0.13189(11) 0.65609(11) 0.1044(8) Uani 1 1 d . . . . .
H2 H -0.0092 0.0840 0.6466 0.157 Uiso 1 1 calc R U . . .
N1 N 0.49709(18) 0.29175(10) 0.31761(11) 0.0552(4) Uani 1 1 d . . . . .
H1 H 0.4872 0.3156 0.2676 0.066 Uiso 1 1 calc R U . . .
N2 N 0.40527(17) 0.18977(9) 0.40770(10) 0.0484(4) Uani 1 1 d . . . . .
N3 N 0.28063(19) 0.08257(10) 0.46978(10) 0.0563(4) Uani 1 1 d . . . . .
H3 H 0.2119 0.0494 0.4671 0.068 Uiso 1 1 calc R U . . .
N4 N 0.37308(18) 0.07719(10) 0.53832(10) 0.0525(4) Uani 1 1 d . . . . .
O1 O 0.06629(17) 0.03213(9) 0.36650(10) 0.0647(4) Uani 1 1 d . . . . .
C25 C -0.1138(5) 0.1486(2) 0.5101(2) 0.1322(15) Uani 1 1 d . . . . .
H25A H -0.1036 0.1815 0.4585 0.198 Uiso 1 1 calc R U . . .
H25B H -0.0934 0.0929 0.4963 0.198 Uiso 1 1 calc R U . . .
H25C H -0.2071 0.1526 0.5305 0.198 Uiso 1 1 calc R U . . .
S1 S 0.25709(6) 0.22515(3) 0.26812(3) 0.05326(16) Uani 1 1 d . . . . .
Cl1 Cl -0.26566(8) 0.13224(6) -0.00540(5) 0.0980(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C4 1.409(3) . ?
C1 C3 1.412(3) . ?
C1 S1 1.752(2) . ?
C2 N2 1.309(2) . ?
C2 N1 1.339(3) . ?
C2 S1 1.7488(19) . ?
C3 N3 1.343(2) . ?
C3 N2 1.351(2) . ?
C4 O1 1.258(2) . ?
C4 C5 1.494(3) . ?
C5 C10 1.384(3) . ?
C5 C6 1.387(3) . ?
C6 C7 1.377(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.373(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.376(3) . ?
C8 Cl1 1.742(2) . ?
C9 C10 1.386(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.384(3) . ?
C11 C16 1.385(3) . ?
C11 N1 1.417(2) . ?
C12 C13 1.378(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.372(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.369(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 N4 1.269(2) . ?
C17 C18 1.459(3) . ?
C17 H17 0.9300 . ?
C18 C23 1.388(3) . ?
C18 C19 1.389(3) . ?
C19 C20 1.386(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.369(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.374(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.381(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 O2 1.410(4) . ?
C24 C25 1.423(5) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
O2 H2 0.8200 . ?
N1 H1 0.8600 . ?
N3 N4 1.367(2) . ?
N3 H3 0.8600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

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
_geom_angle_publ_flag
C4 C1 C3 125.55(18) . . ?
C4 C1 S1 126.29(15) . . ?
C3 C1 S1 107.55(14) . . ?
N2 C2 N1 124.75(17) . . ?
N2 C2 S1 116.52(15) . . ?
N1 C2 S1 118.73(14) . . ?
N3 C3 N2 120.51(17) . . ?
N3 C3 C1 121.84(18) . . ?
N2 C3 C1 117.64(17) . . ?
O1 C4 C1 121.22(18) . . ?
O1 C4 C5 118.92(17) . . ?
C1 C4 C5 119.84(18) . . ?
C10 C5 C6 118.65(19) . . ?
C10 C5 C4 122.34(18) . . ?
C6 C5 C4 119.00(19) . . ?
C7 C6 C5 121.0(2) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C8 C7 C6 119.1(2) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C7 C8 C9 121.6(2) . . ?
C7 C8 Cl1 119.22(19) . . ?
C9 C8 Cl1 119.2(2) . . ?
C8 C9 C10 118.7(2) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C5 C10 C9 121.0(2) . . ?
C5 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C12 C11 C16 119.51(18) . . ?
C12 C11 N1 117.63(17) . . ?
C16 C11 N1 122.77(18) . . ?
C13 C12 C11 120.0(2) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 120.6(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 119.3(2) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 121.2(2) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C11 119.4(2) . . ?
C15 C16 H16 120.3 . . ?
C11 C16 H16 120.3 . . ?
N4 C17 C18 121.17(19) . . ?
N4 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C23 C18 C19 118.86(19) . . ?
C23 C18 C17 121.62(18) . . ?
C19 C18 C17 119.51(19) . . ?
C20 C19 C18 120.2(2) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C19 120.3(2) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 119.9(2) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C21 C22 C23 120.5(2) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C18 120.19(19) . . ?
C22 C23 H23 119.9 . . ?
C18 C23 H23 119.9 . . ?
O2 C24 C25 114.0(3) . . ?
O2 C24 H24A 108.8 . . ?
C25 C24 H24A 108.8 . . ?
O2 C24 H24B 108.8 . . ?
C25 C24 H24B 108.8 . . ?
H24A C24 H24B 107.7 . . ?
C24 O2 H2 109.5 . . ?
C2 N1 C11 127.18(16) . . ?
C2 N1 H1 116.4 . . ?
C11 N1 H1 116.4 . . ?
C2 N2 C3 109.61(16) . . ?
C3 N3 N4 121.04(16) . . ?
C3 N3 H3 119.5 . . ?
N4 N3 H3 119.5 . . ?
C17 N4 N3 116.33(17) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C2 S1 C1 88.63(9) . . ?

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_site_symmetry_A
C16 H16 N2 0.93 2.44 2.956(3) 115.0 .
O2 H2 O1 0.82 1.99 2.739(2) 150.7 3_556
N1 H1 O2 0.86 1.91 2.767(2) 178.1 4_665
N3 H3 O1 0.86 2.08 2.713(2) 129.4 .
C16 H16 N2 0.93 2.44 2.956(3) 115.0 .
O2 H2 O1 0.82 1.99 2.739(2) 150.7 3_556
N1 H1 O2 0.86 1.91 2.767(2) 178.1 4_665
N3 H3 O1 0.86 2.08 2.713(2) 129.4 .

_refine_diff_density_max         0.339
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.040

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol-water(1:1)'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1052983'
_audit_update_record             
;
2015-05-29 deposited with the CCDC.
2015-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
5-benzoyl-4-cyclohexylidenehydrazino-2-phenylaminothiazole
_chemical_name_common            CyHAT
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H22 N4 O S'
_chemical_formula_sum            'C22 H22 N4 O S'
_chemical_formula_weight         390.49

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.987(16)
_cell_length_b                   12.649(16)
_cell_length_c                   14.39(2)
_cell_angle_alpha                102.66(3)
_cell_angle_beta                 106.82(2)
_cell_angle_gamma                93.196(12)
_cell_volume                     2021(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3432
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Acicular
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.180
_shelx_estimated_absorpt_T_min   0.915
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
R. H. Blessing Acta Crystallogr., Sect. A, 1995, 51, 33-38
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16490
_diffrn_reflns_av_unetI/netI     0.3272
_diffrn_reflns_av_R_equivalents  0.1209
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.022
_diffrn_reflns_theta_max         26.350
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             8003
_reflns_number_gt                1748
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r14k (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r14k (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r14k (Rigaku, 2012)
;
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0268P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8003
_refine_ls_number_parameters     505
_refine_ls_number_restraints     336
_refine_ls_R_factor_all          0.1780
_refine_ls_R_factor_gt           0.0651
_refine_ls_wR_factor_ref         0.1437
_refine_ls_wR_factor_gt          0.1079
_refine_ls_goodness_of_fit_ref   0.605
_refine_ls_restrained_S_all      0.594
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C22 C 0.4159(4) 0.9708(4) 0.3579(4) 0.0423(14) Uani 1 1 d . U . . .
C24 C 0.4487(4) 0.8011(4) 0.3418(4) 0.0480(15) Uani 1 1 d . U . . .
C25 C 0.3682(4) 0.7975(3) 0.3953(4) 0.0472(15) Uani 1 1 d . U . . .
C26 C 0.3200(4) 0.7027(4) 0.4137(4) 0.0540(16) Uani 1 1 d . U . . .
C27 C 0.2305(4) 0.7046(4) 0.4662(4) 0.0495(15) Uani 1 1 d . U . . .
C28 C 0.1336(5) 0.6250(4) 0.4295(4) 0.0725(19) Uani 1 1 d . U . . .
H28 H 0.1257 0.5710 0.3717 0.087 Uiso 1 1 calc R U . . .
C29 C 0.0489(5) 0.6242(5) 0.4763(5) 0.076(2) Uani 1 1 d . U . . .
H29 H -0.0168 0.5716 0.4498 0.092 Uiso 1 1 calc R U . . .
C210 C 0.0630(6) 0.7034(5) 0.5643(6) 0.090(3) Uani 1 1 d . U . . .
H210 H 0.0065 0.7024 0.5969 0.108 Uiso 1 1 calc R U . . .
C211 C 0.1583(5) 0.7830(4) 0.6044(4) 0.074(2) Uani 1 1 d . U . . .
H211 H 0.1678 0.8347 0.6639 0.089 Uiso 1 1 calc R U . . .
C212 C 0.2405(4) 0.7834(4) 0.5523(4) 0.0597(16) Uani 1 1 d . U . . .
H212 H 0.3038 0.8385 0.5766 0.072 Uiso 1 1 calc R U . . .
C213 C 0.3841(4) 1.1713(3) 0.3831(4) 0.0475(15) Uani 1 1 d . U . . .
C214 C 0.3097(5) 1.1779(4) 0.4397(4) 0.0697(19) Uani 1 1 d . U . . .
H214 H 0.2803 1.1150 0.4528 0.084 Uiso 1 1 calc R U . . .
C215 C 0.2776(5) 1.2791(4) 0.4782(4) 0.080(2) Uani 1 1 d . U . . .
H215 H 0.2313 1.2840 0.5205 0.096 Uiso 1 1 calc R U . . .
C216 C 0.3145(5) 1.3714(4) 0.4536(4) 0.0743(19) Uani 1 1 d . U . . .
H216 H 0.2904 1.4381 0.4766 0.089 Uiso 1 1 calc R U . . .
C217 C 0.3880(5) 1.3638(4) 0.3942(4) 0.083(2) Uani 1 1 d . U . . .
H217 H 0.4146 1.4260 0.3784 0.099 Uiso 1 1 calc R U . . .
C218 C 0.4219(5) 1.2638(4) 0.3584(4) 0.0671(18) Uani 1 1 d . U . . .
H218 H 0.4701 1.2589 0.3177 0.081 Uiso 1 1 calc R U . . .
C219 C 0.6117(5) 0.6226(4) 0.2275(4) 0.0614(17) Uani 1 1 d . U . . .
C220 C 0.7064(4) 0.6225(4) 0.1788(4) 0.0673(18) Uani 1 1 d . U . . .
H22A H 0.7352 0.6971 0.1831 0.081 Uiso 1 1 calc R U . . .
H23A H 0.6742 0.5850 0.1085 0.081 Uiso 1 1 calc R U . . .
C221 C 0.8073(5) 0.5666(4) 0.2285(5) 0.094(2) Uani 1 1 d . U . . .
H24A H 0.8465 0.6102 0.2960 0.113 Uiso 1 1 calc R U . . .
H25A H 0.8638 0.5623 0.1917 0.113 Uiso 1 1 calc R U . . .
C222 C 0.7672(5) 0.4525(4) 0.2330(5) 0.096(2) Uani 1 1 d . U . . .
H26A H 0.8333 0.4230 0.2714 0.115 Uiso 1 1 calc R U . . .
H27A H 0.7393 0.4054 0.1657 0.115 Uiso 1 1 calc R U . . .
C223 C 0.6697(6) 0.4529(4) 0.2809(5) 0.115(3) Uani 1 1 d . U . . .
H29A H 0.6398 0.3780 0.2750 0.138 Uiso 1 1 calc R U . . .
H28A H 0.7019 0.4885 0.3516 0.138 Uiso 1 1 calc R U . . .
C224 C 0.5703(5) 0.5099(4) 0.2343(5) 0.103(3) Uani 1 1 d . U . . .
H30A H 0.5164 0.5166 0.2736 0.123 Uiso 1 1 calc R U . . .
H31A H 0.5278 0.4661 0.1675 0.123 Uiso 1 1 calc R U . . .
N22 N 0.4232(3) 1.0727(3) 0.3412(3) 0.0504(12) Uani 1 1 d . U . . .
H22 H 0.4575 1.0786 0.2974 0.060 Uiso 1 1 calc R U . . .
N23 N 0.4762(3) 0.8985(3) 0.3227(3) 0.0455(12) Uani 1 1 d . U . . .
N24 N 0.4963(3) 0.7112(3) 0.3087(3) 0.0575(13) Uani 1 1 d . U . . .
H24 H 0.4734 0.6499 0.3181 0.069 Uiso 1 1 calc R U . . .
N219 N 0.5800(3) 0.7146(3) 0.2606(3) 0.0537(13) Uani 1 1 d . U . . .
O26 O 0.3481(3) 0.6093(2) 0.3783(3) 0.0801(14) Uani 1 1 d . U . . .
S21 S 0.32544(11) 0.92816(9) 0.42180(10) 0.0489(4) Uani 1 1 d . U . . .
C12 C 0.6083(4) 0.0317(4) 0.1702(4) 0.0435(13) Uani 1 1 d . U . . .
C14 C 0.4793(4) 0.1346(4) 0.1056(4) 0.0419(13) Uani 1 1 d . U . . .
C15 C 0.5661(4) 0.1620(3) 0.0638(3) 0.0425(14) Uani 1 1 d . U . . .
C16 C 0.5574(5) 0.2394(4) 0.0058(4) 0.0504(15) Uani 1 1 d . U . . .
C17 C 0.6497(4) 0.2585(4) -0.0443(4) 0.0547(16) Uani 1 1 d . U . . .
C18 C 0.6741(5) 0.3605(4) -0.0586(4) 0.084(2) Uani 1 1 d . U . . .
H18 H 0.6343 0.4170 -0.0366 0.101 Uiso 1 1 calc R U . . .
C19 C 0.7563(6) 0.3801(5) -0.1046(5) 0.108(3) Uani 1 1 d . U . . .
H19 H 0.7758 0.4504 -0.1096 0.130 Uiso 1 1 calc R U . . .
C110 C 0.8096(6) 0.2946(6) -0.1435(5) 0.101(3) Uani 1 1 d . U . . .
H110 H 0.8635 0.3072 -0.1764 0.122 Uiso 1 1 calc R U . . .
C111 C 0.7841(5) 0.1921(5) -0.1340(4) 0.078(2) Uani 1 1 d . U . . .
H111 H 0.8210 0.1351 -0.1595 0.093 Uiso 1 1 calc R U . . .
C112 C 0.7021(4) 0.1731(4) -0.0856(4) 0.0625(17) Uani 1 1 d . U . . .
H112 H 0.6824 0.1027 -0.0811 0.075 Uiso 1 1 calc R U . . .
C113 C 0.7637(5) -0.0709(4) 0.2515(5) 0.0518(16) Uani 1 1 d . U . . .
C114 C 0.8302(5) -0.0842(4) 0.1858(5) 0.079(2) Uani 1 1 d . U . . .
H114 H 0.7998 -0.0769 0.1206 0.095 Uiso 1 1 calc R U . . .
C115 C 0.9435(6) -0.1087(6) 0.2217(7) 0.129(4) Uani 1 1 d . U . . .
H115 H 0.9916 -0.1109 0.1810 0.154 Uiso 1 1 calc R U . . .
C116 C 0.9879(6) -0.1294(6) 0.3118(8) 0.141(4) Uani 1 1 d . U . . .
H116 H 1.0623 -0.1510 0.3312 0.170 Uiso 1 1 calc R U . . .
C117 C 0.9197(6) -0.1175(5) 0.3741(5) 0.096(2) Uani 1 1 d . U . . .
H117 H 0.9493 -0.1295 0.4377 0.116 Uiso 1 1 calc R U . . .
C118 C 0.8090(6) -0.0885(4) 0.3448(5) 0.078(2) Uani 1 1 d . U . . .
H118 H 0.7644 -0.0808 0.3886 0.094 Uiso 1 1 calc R U . . .
C119 C 0.1969(6) 0.1829(5) 0.1118(5) 0.087(2) Uani 1 1 d . U . . .
C120 C 0.0964(5) 0.1259(5) 0.1345(6) 0.139(3) Uani 1 1 d . U . . .
H12A H 0.0421 0.0823 0.0720 0.167 Uiso 1 1 calc R U . . .
H13A H 0.1278 0.0764 0.1754 0.167 Uiso 1 1 calc R U . . .
C121 C 0.0372(6) 0.1926(6) 0.1812(7) 0.167(4) Uani 1 1 d . U . . .
H15A H 0.0826 0.2140 0.2516 0.200 Uiso 1 1 calc R U . . .
H14A H -0.0354 0.1505 0.1760 0.200 Uiso 1 1 calc R U . . .
C122 C 0.0056(5) 0.2957(6) 0.1487(6) 0.127(3) Uani 1 1 d . U . . .
H16A H -0.0621 0.2780 0.0889 0.152 Uiso 1 1 calc R U . . .
H17A H -0.0148 0.3455 0.2010 0.152 Uiso 1 1 calc R U . . .
C123 C 0.1058(6) 0.3487(5) 0.1280(7) 0.207(5) Uani 1 1 d . U . . .
H18A H 0.0752 0.3994 0.0881 0.248 Uiso 1 1 calc R U . . .
H19A H 0.1581 0.3921 0.1915 0.248 Uiso 1 1 calc R U . . .
C124 C 0.1724(6) 0.2869(5) 0.0811(6) 0.135(3) Uani 1 1 d . U . . .
H21A H 0.2468 0.3306 0.0936 0.162 Uiso 1 1 calc R U . . .
H20A H 0.1328 0.2692 0.0095 0.162 Uiso 1 1 calc R U . . .
N12 N 0.6492(3) -0.0406(3) 0.2226(3) 0.0533(13) Uani 1 1 d . U . . .
H12 H 0.5983 -0.0737 0.2416 0.064 Uiso 1 1 calc R U . . .
N13 N 0.5034(3) 0.0625(3) 0.1647(3) 0.0472(12) Uani 1 1 d . U . . .
N14 N 0.3795(3) 0.1796(3) 0.0935(3) 0.0650(15) Uani 1 1 d . U . . .
H14 H 0.3728 0.2372 0.0709 0.078 Uiso 1 1 calc R U . . .
N119 N 0.2860(4) 0.1337(3) 0.1173(3) 0.0659(14) Uani 1 1 d . U . . .
O16 O 0.4763(3) 0.2981(3) -0.0030(3) 0.0818(14) Uani 1 1 d . U . . .
S11 S 0.68343(11) 0.08796(10) 0.10137(11) 0.0547(4) Uani 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C22 N23 1.304(5) . ?
C22 N22 1.364(5) . ?
C22 S21 1.744(4) . ?
C24 N24 1.355(5) . ?
C24 N23 1.362(5) . ?
C24 C25 1.402(5) . ?
C25 C26 1.411(5) . ?
C25 S21 1.753(4) . ?
C26 O26 1.284(5) . ?
C26 C27 1.479(6) . ?
C27 C212 1.380(6) . ?
C27 C28 1.387(6) . ?
C28 C29 1.372(6) . ?
C28 H28 0.9300 . ?
C29 C210 1.391(7) . ?
C29 H29 0.9300 . ?
C210 C211 1.373(7) . ?
C210 H210 0.9300 . ?
C211 C212 1.400(6) . ?
C211 H211 0.9300 . ?
C212 H212 0.9300 . ?
C213 C214 1.366(5) . ?
C213 C218 1.386(5) . ?
C213 N22 1.428(5) . ?
C214 C215 1.400(6) . ?
C214 H214 0.9300 . ?
C215 C216 1.377(6) . ?
C215 H215 0.9300 . ?
C216 C217 1.388(6) . ?
C216 H216 0.9300 . ?
C217 C218 1.387(6) . ?
C217 H217 0.9300 . ?
C218 H218 0.9300 . ?
C219 N219 1.280(5) . ?
C219 C220 1.496(6) . ?
C219 C224 1.516(6) . ?
C220 C221 1.514(6) . ?
C220 H22A 0.9700 . ?
C220 H23A 0.9700 . ?
C221 C222 1.517(6) . ?
C221 H24A 0.9700 . ?
C221 H25A 0.9700 . ?
C222 C223 1.518(6) . ?
C222 H26A 0.9700 . ?
C222 H27A 0.9700 . ?
C223 C224 1.495(7) . ?
C223 H29A 0.9700 . ?
C223 H28A 0.9700 . ?
C224 H30A 0.9700 . ?
C224 H31A 0.9700 . ?
N22 H22 0.8600 . ?
N24 N219 1.378(4) . ?
N24 H24 0.8600 . ?
C12 N13 1.323(5) . ?
C12 N12 1.336(5) . ?
C12 S11 1.747(4) . ?
C14 N14 1.336(5) . ?
C14 N13 1.367(5) . ?
C14 C15 1.406(5) . ?
C15 C16 1.408(6) . ?
C15 S11 1.754(5) . ?
C16 O16 1.251(5) . ?
C16 C17 1.520(6) . ?
C17 C18 1.378(6) . ?
C17 C112 1.388(6) . ?
C18 C19 1.377(6) . ?
C18 H18 0.9300 . ?
C19 C110 1.382(7) . ?
C19 H19 0.9300 . ?
C110 C111 1.360(7) . ?
C110 H110 0.9300 . ?
C111 C112 1.397(5) . ?
C111 H111 0.9300 . ?
C112 H112 0.9300 . ?
C113 C118 1.368(7) . ?
C113 C114 1.392(6) . ?
C113 N12 1.415(6) . ?
C114 C115 1.386(8) . ?
C114 H114 0.9300 . ?
C115 C116 1.340(10) . ?
C115 H115 0.9300 . ?
C116 C117 1.368(8) . ?
C116 H116 0.9300 . ?
C117 C118 1.368(7) . ?
C117 H117 0.9300 . ?
C118 H118 0.9300 . ?
C119 N119 1.256(6) . ?
C119 C124 1.496(7) . ?
C119 C120 1.521(6) . ?
C120 C121 1.326(7) . ?
C120 H12A 0.9700 . ?
C120 H13A 0.9700 . ?
C121 C122 1.511(7) . ?
C121 H15A 0.9700 . ?
C121 H14A 0.9700 . ?
C122 C123 1.478(7) . ?
C122 H16A 0.9700 . ?
C122 H17A 0.9700 . ?
C123 C124 1.362(7) . ?
C123 H18A 0.9700 . ?
C123 H19A 0.9700 . ?
C124 H21A 0.9700 . ?
C124 H20A 0.9700 . ?
N12 H12 0.8600 . ?
N14 N119 1.395(4) . ?
N14 H14 0.8600 . ?

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
_geom_angle_publ_flag
N23 C22 N22 119.8(4) . . ?
N23 C22 S21 116.5(3) . . ?
N22 C22 S21 123.6(3) . . ?
N24 C24 N23 120.9(4) . . ?
N24 C24 C25 121.7(4) . . ?
N23 C24 C25 117.4(4) . . ?
C24 C25 C26 125.8(4) . . ?
C24 C25 S21 107.7(3) . . ?
C26 C25 S21 126.1(3) . . ?
O26 C26 C25 119.6(4) . . ?
O26 C26 C27 117.5(4) . . ?
C25 C26 C27 122.7(4) . . ?
C212 C27 C28 118.1(5) . . ?
C212 C27 C26 121.9(5) . . ?
C28 C27 C26 120.0(5) . . ?
C29 C28 C27 121.5(6) . . ?
C29 C28 H28 119.3 . . ?
C27 C28 H28 119.3 . . ?
C28 C29 C210 118.9(6) . . ?
C28 C29 H29 120.6 . . ?
C210 C29 H29 120.6 . . ?
C211 C210 C29 121.8(6) . . ?
C211 C210 H210 119.1 . . ?
C29 C210 H210 119.1 . . ?
C210 C211 C212 117.6(6) . . ?
C210 C211 H211 121.2 . . ?
C212 C211 H211 121.2 . . ?
C27 C212 C211 122.1(5) . . ?
C27 C212 H212 119.0 . . ?
C211 C212 H212 119.0 . . ?
C214 C213 C218 119.9(4) . . ?
C214 C213 N22 124.7(4) . . ?
C218 C213 N22 115.3(4) . . ?
C213 C214 C215 120.2(4) . . ?
C213 C214 H214 119.9 . . ?
C215 C214 H214 119.9 . . ?
C216 C215 C214 120.2(5) . . ?
C216 C215 H215 119.9 . . ?
C214 C215 H215 119.9 . . ?
C215 C216 C217 119.3(5) . . ?
C215 C216 H216 120.3 . . ?
C217 C216 H216 120.3 . . ?
C218 C217 C216 120.3(5) . . ?
C218 C217 H217 119.9 . . ?
C216 C217 H217 119.9 . . ?
C213 C218 C217 120.1(4) . . ?
C213 C218 H218 120.0 . . ?
C217 C218 H218 120.0 . . ?
N219 C219 C220 117.9(4) . . ?
N219 C219 C224 128.9(5) . . ?
C220 C219 C224 113.2(4) . . ?
C219 C220 C221 111.2(4) . . ?
C219 C220 H22A 109.4 . . ?
C221 C220 H22A 109.4 . . ?
C219 C220 H23A 109.4 . . ?
C221 C220 H23A 109.4 . . ?
H22A C220 H23A 108.0 . . ?
C220 C221 C222 112.4(5) . . ?
C220 C221 H24A 109.1 . . ?
C222 C221 H24A 109.1 . . ?
C220 C221 H25A 109.1 . . ?
C222 C221 H25A 109.1 . . ?
H24A C221 H25A 107.8 . . ?
C221 C222 C223 111.4(4) . . ?
C221 C222 H26A 109.3 . . ?
C223 C222 H26A 109.3 . . ?
C221 C222 H27A 109.3 . . ?
C223 C222 H27A 109.3 . . ?
H26A C222 H27A 108.0 . . ?
C224 C223 C222 113.0(5) . . ?
C224 C223 H29A 109.0 . . ?
C222 C223 H29A 109.0 . . ?
C224 C223 H28A 109.0 . . ?
C222 C223 H28A 109.0 . . ?
H29A C223 H28A 107.8 . . ?
C223 C224 C219 112.4(5) . . ?
C223 C224 H30A 109.1 . . ?
C219 C224 H30A 109.1 . . ?
C223 C224 H31A 109.1 . . ?
C219 C224 H31A 109.1 . . ?
H30A C224 H31A 107.9 . . ?
C22 N22 C213 131.7(4) . . ?
C22 N22 H22 114.2 . . ?
C213 N22 H22 114.2 . . ?
C22 N23 C24 109.6(4) . . ?
C24 N24 N219 122.4(3) . . ?
C24 N24 H24 118.8 . . ?
N219 N24 H24 118.8 . . ?
C219 N219 N24 115.9(4) . . ?
C22 S21 C25 88.7(2) . . ?
N13 C12 N12 120.6(4) . . ?
N13 C12 S11 115.4(4) . . ?
N12 C12 S11 123.9(4) . . ?
N14 C14 N13 120.0(4) . . ?
N14 C14 C15 122.9(4) . . ?
N13 C14 C15 117.0(4) . . ?
C14 C15 C16 123.9(4) . . ?
C14 C15 S11 107.9(3) . . ?
C16 C15 S11 128.2(3) . . ?
O16 C16 C15 121.3(4) . . ?
O16 C16 C17 117.4(4) . . ?
C15 C16 C17 121.2(4) . . ?
C18 C17 C112 118.4(5) . . ?
C18 C17 C16 119.8(5) . . ?
C112 C17 C16 121.5(4) . . ?
C19 C18 C17 121.2(5) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C110 119.5(6) . . ?
C18 C19 H19 120.2 . . ?
C110 C19 H19 120.2 . . ?
C111 C110 C19 120.6(6) . . ?
C111 C110 H110 119.7 . . ?
C19 C110 H110 119.7 . . ?
C110 C111 C112 119.6(6) . . ?
C110 C111 H111 120.2 . . ?
C112 C111 H111 120.2 . . ?
C17 C112 C111 120.5(5) . . ?
C17 C112 H112 119.7 . . ?
C111 C112 H112 119.7 . . ?
C118 C113 C114 119.7(5) . . ?
C118 C113 N12 119.5(5) . . ?
C114 C113 N12 120.8(5) . . ?
C115 C114 C113 117.2(6) . . ?
C115 C114 H114 121.4 . . ?
C113 C114 H114 121.4 . . ?
C116 C115 C114 123.7(7) . . ?
C116 C115 H115 118.2 . . ?
C114 C115 H115 118.2 . . ?
C115 C116 C117 117.6(8) . . ?
C115 C116 H116 121.2 . . ?
C117 C116 H116 121.2 . . ?
C116 C117 C118 121.4(7) . . ?
C116 C117 H117 119.3 . . ?
C118 C117 H117 119.3 . . ?
C113 C118 C117 120.2(6) . . ?
C113 C118 H118 119.9 . . ?
C117 C118 H118 119.9 . . ?
N119 C119 C124 129.5(5) . . ?
N119 C119 C120 115.7(5) . . ?
C124 C119 C120 114.7(5) . . ?
C121 C120 C119 114.7(6) . . ?
C121 C120 H12A 108.6 . . ?
C119 C120 H12A 108.6 . . ?
C121 C120 H13A 108.6 . . ?
C119 C120 H13A 108.6 . . ?
H12A C120 H13A 107.6 . . ?
C120 C121 C122 119.8(7) . . ?
C120 C121 H15A 107.4 . . ?
C122 C121 H15A 107.4 . . ?
C120 C121 H14A 107.4 . . ?
C122 C121 H14A 107.4 . . ?
H15A C121 H14A 106.9 . . ?
C123 C122 C121 110.2(5) . . ?
C123 C122 H16A 109.6 . . ?
C121 C122 H16A 109.6 . . ?
C123 C122 H17A 109.6 . . ?
C121 C122 H17A 109.6 . . ?
H16A C122 H17A 108.1 . . ?
C124 C123 C122 120.1(6) . . ?
C124 C123 H18A 107.3 . . ?
C122 C123 H18A 107.3 . . ?
C124 C123 H19A 107.3 . . ?
C122 C123 H19A 107.3 . . ?
H18A C123 H19A 106.9 . . ?
C123 C124 C119 115.4(6) . . ?
C123 C124 H21A 108.4 . . ?
C119 C124 H21A 108.4 . . ?
C123 C124 H20A 108.4 . . ?
C119 C124 H20A 108.4 . . ?
H21A C124 H20A 107.5 . . ?
C12 N12 C113 129.6(4) . . ?
C12 N12 H12 115.2 . . ?
C113 N12 H12 115.2 . . ?
C12 N13 C14 110.3(4) . . ?
C14 N14 N119 120.5(4) . . ?
C14 N14 H14 119.7 . . ?
N119 N14 H14 119.7 . . ?
C119 N119 N14 118.5(4) . . ?
C12 S11 C15 89.4(2) . . ?

_refine_diff_density_max         0.276
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.064

# start Validation Reply Form
_vrf_PLAT026_shelx               
;
PROBLEM: Ratio Observed / Unique Reflections too Low ....         22 %     
RESPONSE: The crystal diffraction for the ligand was poor. Only 3986 reflections out of the observed 17936 reflections 
(theta max = 14.0) were of I/sig(I) >2, which is considered as relevant data. The compound diffracted weakly
especially in the higher angles leading to a poor observed/unique reflections ratio (22%). 
;
_vrf_PLAT241_shelx               
;
PROBLEM: High      Ueq as Compared to Neighbors for .....       C123 Check 
RESPONSE: Associated with the thermal vibration of the conformationally flexible
cyclohexane group
;
_vrf_PLAT242_shelx               
;
PROBLEM: Low       Ueq as Compared to Neighbors for .....       C122 Check 
RESPONSE: Associated with the thermal vibration of the conformationally flexible
cyclohexane group
;
_vrf_PLAT360_shelx               
;
PROBLEM: Short  C(sp3)-C(sp3) Bond  C120   -   C121   ...       1.33 Ang.  
RESPONSE: Associated with the thermal vibration of the conformationally flexible
cyclohexane group
;
# end Validation Reply Form

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol-water (1:1)'
