# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_I
_database_code_depnum_ccdc_archive 'CCDC 1036467'
_audit_update_record             
;
2015-03-24 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
(2E)-N-(3-methylphenyl)-2-{2-[(2-oxo-2H-chromen-3-yl)methoxy]benzylidene}hydrazinecarbothioamide
_chemical_formula_moiety         'C25 H21 N3 O3 S'
_chemical_formula_sum            'C25 H21 N3 O3 S'
_chemical_formula_iupac          'C25 H21 N3 O3 S'
_chemical_formula_weight         443.51

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                   7.2519(3)
_cell_length_b                   11.3182(5)
_cell_length_c                   13.2908(7)
_cell_angle_alpha                91.507(2)
_cell_angle_beta                 98.145(3)
_cell_angle_gamma                94.768(2)
_cell_volume                     1075.35(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3847
_cell_measurement_theta_min      2.848
_cell_measurement_theta_max      27.000
_cell_measurement_temperature    296(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_T_max  0.957
_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.70
_diffrn_reflns_number            16919
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.848
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total             4689
_reflns_number_gt                3847
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.1052
_refine_ls_wR_factor_gt          0.0969
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_number_reflns         4689
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0525P)²+0.2223P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;


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
S1 S 0.47455(5) 0.17667(3) -0.08057(3) 0.05102(13) Uani 1 1 d . . . . .
O1 O 1.04422(15) -0.19879(11) 0.63011(8) 0.0591(3) Uani 1 1 d . . . . .
O2 O 0.75366(14) -0.27885(9) 0.59501(7) 0.0467(2) Uani 1 1 d . . . . .
O3 O 1.05481(14) -0.09298(10) 0.33344(8) 0.0528(3) Uani 1 1 d . . . . .
N1 N 0.93316(15) 0.10050(10) 0.08741(8) 0.0388(3) Uani 1 1 d . . . . .
N2 N 0.75183(16) 0.09324(10) 0.03882(8) 0.0413(3) Uani 1 1 d . . . . .
H2 H 0.6743 0.0340 0.0477 0.050 Uiso 1 1 calc R U . . .
N3 N 0.83479(16) 0.26484(10) -0.03267(9) 0.0440(3) Uani 1 1 d . . . . .
H3A H 0.9434 0.2500 -0.0032 0.053 Uiso 1 1 calc R U . . .
C1 C 0.9102(2) -0.22170(13) 0.56565(11) 0.0433(3) Uani 1 1 d . . . . .
C2 C 0.5950(2) -0.31206(12) 0.52678(10) 0.0412(3) Uani 1 1 d . . . . .
C3 C 0.4461(2) -0.36903(13) 0.56554(12) 0.0496(4) Uani 1 1 d . . . . .
H3 H 0.4523 -0.3807 0.6349 0.059 Uiso 1 1 calc R U . . .
C4 C 0.2883(2) -0.40818(14) 0.49916(14) 0.0571(4) Uani 1 1 d . . . . .
H4 H 0.1868 -0.4472 0.5237 0.068 Uiso 1 1 calc R U . . .
C5 C 0.2794(3) -0.38971(16) 0.39526(14) 0.0624(4) Uani 1 1 d . . . . .
H5 H 0.1729 -0.4176 0.3509 0.075 Uiso 1 1 calc R U . . .
C6 C 0.4267(2) -0.33063(15) 0.35824(12) 0.0563(4) Uani 1 1 d . . . . .
H6 H 0.4184 -0.3174 0.2890 0.068 Uiso 1 1 calc R U . . .
C7 C 0.5896(2) -0.29011(12) 0.42358(11) 0.0441(3) Uani 1 1 d . . . . .
C8 C 0.7510(2) -0.22675(12) 0.39166(11) 0.0459(3) Uani 1 1 d . . . . .
H8 H 0.7491 -0.2091 0.3236 0.055 Uiso 1 1 calc R U . . .
C9 C 0.9036(2) -0.19293(12) 0.45863(10) 0.0413(3) Uani 1 1 d . . . . .
C10 C 1.0805(2) -0.12785(13) 0.43602(11) 0.0448(3) Uani 1 1 d . . . . .
H6A H 1.1125 -0.0584 0.4814 0.054 Uiso 1 1 calc R U . . .
H6B H 1.1821 -0.1788 0.4467 0.054 Uiso 1 1 calc R U . . .
C11 C 1.20252(19) -0.02560(12) 0.30338(11) 0.0412(3) Uani 1 1 d . . . . .
C12 C 1.3813(2) -0.01323(14) 0.35852(12) 0.0505(4) Uani 1 1 d . . . . .
H12 H 1.4061 -0.0523 0.4190 0.061 Uiso 1 1 calc R U . . .
C13 C 1.5220(2) 0.05699(15) 0.32363(13) 0.0527(4) Uani 1 1 d . . . . .
H13 H 1.6415 0.0646 0.3606 0.063 Uiso 1 1 calc R U . . .
C14 C 1.4868(2) 0.11616(14) 0.23414(12) 0.0495(4) Uani 1 1 d . . . . .
H14 H 1.5816 0.1640 0.2112 0.059 Uiso 1 1 calc R U . . .
C15 C 1.3098(2) 0.10364(12) 0.17924(11) 0.0431(3) Uani 1 1 d . . . . .
H15 H 1.2871 0.1426 0.1186 0.052 Uiso 1 1 calc R U . . .
C16 C 1.16385(19) 0.03402(11) 0.21228(10) 0.0375(3) Uani 1 1 d . . . . .
C17 C 0.97347(19) 0.02771(12) 0.15736(10) 0.0400(3) Uani 1 1 d . . . . .
H9 H 0.8825 -0.0288 0.1732 0.048 Uiso 1 1 calc R U . . .
C18 C 0.69724(19) 0.18103(11) -0.02334(9) 0.0372(3) Uani 1 1 d . . . . .
C19 C 0.83172(18) 0.37414(11) -0.08299(10) 0.0370(3) Uani 1 1 d . . . . .
C20 C 0.68782(19) 0.44715(12) -0.08438(11) 0.0444(3) Uani 1 1 d . . . . .
H20 H 0.5805 0.4232 -0.0568 0.053 Uiso 1 1 calc R U . . .
C21 C 0.7068(2) 0.55710(13) -0.12793(12) 0.0502(4) Uani 1 1 d . . . . .
H21 H 0.6107 0.6069 -0.1293 0.060 Uiso 1 1 calc R U . . .
C22 C 0.8647(2) 0.59374(12) -0.16909(11) 0.0475(4) Uani 1 1 d . . . . .
H22 H 0.8741 0.6676 -0.1980 0.057 Uiso 1 1 calc R U . . .
C23 C 1.0097(2) 0.52123(13) -0.16771(11) 0.0451(3) Uani 1 1 d . . . . .
C24 C 0.99097(19) 0.41086(12) -0.12432(11) 0.0420(3) Uani 1 1 d . . . . .
H24 H 1.0869 0.3611 -0.1231 0.050 Uiso 1 1 calc R U . . .
C25 C 1.1838(3) 0.56074(19) -0.21127(17) 0.0749(6) Uani 1 1 d . . . . .
H25 H 1.2783 0.5937 -0.1577 0.112 Uiso 1 1 calc R U . . .
H13B H 1.1563 0.6198 -0.2604 0.112 Uiso 1 1 calc R U . . .
H13C H 1.2281 0.4940 -0.2436 0.112 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
S1 C18 1.6810(13) . ?
O1 C1 1.2067(18) . ?
O2 C1 1.3699(17) . ?
O2 C2 1.3792(17) . ?
O3 C11 1.3747(16) . ?
O3 C10 1.4204(16) . ?
N1 C17 1.2774(16) . ?
N1 N2 1.3754(15) . ?
N2 C18 1.3574(17) . ?
N2 H2 0.8600 . ?
N3 C18 1.3394(16) . ?
N3 C19 1.4221(16) . ?
N3 H3A 0.8600 . ?
C1 C9 1.4625(19) . ?
C2 C3 1.381(2) . ?
C2 C7 1.396(2) . ?
C3 C4 1.376(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.395(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.399(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.443(2) . ?
C8 C9 1.340(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.498(2) . ?
C10 H6A 0.9700 . ?
C10 H6B 0.9700 . ?
C11 C12 1.3900(19) . ?
C11 C16 1.4065(18) . ?
C12 C13 1.381(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.383(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.3947(19) . ?
C15 H15 0.9300 . ?
C16 C17 1.4627(18) . ?
C17 H9 0.9300 . ?
C19 C20 1.382(2) . ?
C19 C24 1.3856(19) . ?
C20 C21 1.391(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.376(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.385(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.3940(19) . ?
C23 C25 1.502(2) . ?
C24 H24 0.9300 . ?
C25 H25 0.9600 . ?
C25 H13B 0.9600 . ?
C25 H13C 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
C1 O2 C2 122.12(11) . . ?
C11 O3 C10 115.82(11) . . ?
C17 N1 N2 117.72(11) . . ?
C18 N2 N1 118.94(10) . . ?
C18 N2 H2 120.5 . . ?
N1 N2 H2 120.5 . . ?
C18 N3 C19 130.94(11) . . ?
C18 N3 H3A 114.5 . . ?
C19 N3 H3A 114.5 . . ?
O1 C1 O2 117.52(13) . . ?
O1 C1 C9 124.60(14) . . ?
O2 C1 C9 117.87(12) . . ?
O2 C2 C3 116.76(12) . . ?
O2 C2 C7 120.65(13) . . ?
C3 C2 C7 122.58(14) . . ?
C4 C3 C2 118.47(15) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C5 120.47(16) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.38(15) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 120.61(15) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C2 C7 C6 117.48(14) . . ?
C2 C7 C8 118.02(13) . . ?
C6 C7 C8 124.50(14) . . ?
C9 C8 C7 120.98(13) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C1 120.24(13) . . ?
C8 C9 C10 126.61(13) . . ?
C1 C9 C10 113.13(12) . . ?
O3 C10 C9 109.22(11) . . ?
O3 C10 H6A 109.8 . . ?
C9 C10 H6A 109.8 . . ?
O3 C10 H6B 109.8 . . ?
C9 C10 H6B 109.8 . . ?
H6A C10 H6B 108.3 . . ?
O3 C11 C12 123.58(12) . . ?
O3 C11 C16 116.24(12) . . ?
C12 C11 C16 120.18(13) . . ?
C13 C12 C11 120.10(14) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 120.56(14) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 119.39(13) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 121.70(13) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C15 C16 C11 118.06(12) . . ?
C15 C16 C17 121.38(12) . . ?
C11 C16 C17 120.48(12) . . ?
N1 C17 C16 119.43(12) . . ?
N1 C17 H9 120.3 . . ?
C16 C17 H9 120.3 . . ?
N3 C18 N2 113.76(11) . . ?
N3 C18 S1 126.34(10) . . ?
N2 C18 S1 119.90(9) . . ?
C20 C19 C24 120.11(12) . . ?
C20 C19 N3 123.43(12) . . ?
C24 C19 N3 116.23(12) . . ?
C19 C20 C21 118.66(13) . . ?
C19 C20 H20 120.7 . . ?
C21 C20 H20 120.7 . . ?
C22 C21 C20 121.35(14) . . ?
C22 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C21 C22 C23 120.33(13) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C24 118.46(13) . . ?
C22 C23 C25 120.87(14) . . ?
C24 C23 C25 120.67(15) . . ?
C19 C24 C23 121.09(14) . . ?
C19 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C23 C25 H25 109.5 . . ?
C23 C25 H13B 109.5 . . ?
H25 C25 H13B 109.5 . . ?
C23 C25 H13C 109.5 . . ?
H25 C25 H13C 109.5 . . ?
H13B C25 H13C 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
C17 N1 N2 C18 169.14(13) . . . . ?
C2 O2 C1 O1 -178.12(13) . . . . ?
C2 O2 C1 C9 1.78(19) . . . . ?
C1 O2 C2 C3 -179.95(12) . . . . ?
C1 O2 C2 C7 1.15(19) . . . . ?
O2 C2 C3 C4 -177.20(13) . . . . ?
C7 C2 C3 C4 1.7(2) . . . . ?
C2 C3 C4 C5 -0.4(2) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
C4 C5 C6 C7 1.3(3) . . . . ?
O2 C2 C7 C6 177.43(13) . . . . ?
C3 C2 C7 C6 -1.4(2) . . . . ?
O2 C2 C7 C8 -2.99(19) . . . . ?
C3 C2 C7 C8 178.18(13) . . . . ?
C5 C6 C7 C2 -0.1(2) . . . . ?
C5 C6 C7 C8 -179.67(14) . . . . ?
C2 C7 C8 C9 1.9(2) . . . . ?
C6 C7 C8 C9 -178.58(14) . . . . ?
C7 C8 C9 C1 1.0(2) . . . . ?
C7 C8 C9 C10 179.49(13) . . . . ?
O1 C1 C9 C8 177.02(15) . . . . ?
O2 C1 C9 C8 -2.9(2) . . . . ?
O1 C1 C9 C10 -1.6(2) . . . . ?
O2 C1 C9 C10 178.47(12) . . . . ?
C11 O3 C10 C9 176.12(12) . . . . ?
C8 C9 C10 O3 7.4(2) . . . . ?
C1 C9 C10 O3 -174.03(12) . . . . ?
C10 O3 C11 C12 14.4(2) . . . . ?
C10 O3 C11 C16 -164.56(13) . . . . ?
O3 C11 C12 C13 -179.43(14) . . . . ?
C16 C11 C12 C13 -0.5(2) . . . . ?
C11 C12 C13 C14 0.4(2) . . . . ?
C12 C13 C14 C15 -0.6(2) . . . . ?
C13 C14 C15 C16 0.9(2) . . . . ?
C14 C15 C16 C11 -1.0(2) . . . . ?
C14 C15 C16 C17 175.70(13) . . . . ?
O3 C11 C16 C15 179.81(12) . . . . ?
C12 C11 C16 C15 0.8(2) . . . . ?
O3 C11 C16 C17 3.1(2) . . . . ?
C12 C11 C16 C17 -175.96(13) . . . . ?
N2 N1 C17 C16 -178.80(12) . . . . ?
C15 C16 C17 N1 -10.9(2) . . . . ?
C11 C16 C17 N1 165.73(13) . . . . ?
C19 N3 C18 N2 -174.28(14) . . . . ?
C19 N3 C18 S1 6.1(2) . . . . ?
N1 N2 C18 N3 2.42(18) . . . . ?
N1 N2 C18 S1 -177.95(10) . . . . ?
C18 N3 C19 C20 37.8(2) . . . . ?
C18 N3 C19 C24 -147.81(15) . . . . ?
C24 C19 C20 C21 0.1(2) . . . . ?
N3 C19 C20 C21 174.23(13) . . . . ?
C19 C20 C21 C22 0.0(2) . . . . ?
C20 C21 C22 C23 -0.2(2) . . . . ?
C21 C22 C23 C24 0.3(2) . . . . ?
C21 C22 C23 C25 -179.28(15) . . . . ?
C20 C19 C24 C23 0.1(2) . . . . ?
N3 C19 C24 C23 -174.49(12) . . . . ?
C22 C23 C24 C19 -0.3(2) . . . . ?
C25 C23 C24 C19 179.33(15) . . . . ?

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
N2 H2 S1 0.86 2.61 3.4422(11) 163.7 2_655
N3 H3A N1 0.86 2.11 2.5631(15) 112.7 .
C20 H20 S1 0.93 2.83 3.3181(14) 114.0 .

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.040

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1036468'
_audit_update_record             
;
2015-03-24 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
(2E)-N-(2,4-dichlorophenyl)-2-(2,3,4,4a-tetrahydro-1H-xanthen-1-ylidene)hydrazinecarbothioamide
_chemical_formula_moiety         '2(C25 H21 N3 O4 S), 0.5(C4 H8 O2)'
_chemical_formula_sum            'C52 H46 N6 O9  S2'
_chemical_formula_iupac          'C52 H46 N6 O9  S2'
_chemical_formula_weight         963.06

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                   13.2436(6)
_cell_length_b                   18.3753(10)
_cell_length_c                   19.6353(11)
_cell_angle_alpha                90
_cell_angle_beta                 102.698(2)
_cell_angle_gamma                90
_cell_volume                     4661.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6744
_cell_measurement_theta_min      2.362
_cell_measurement_theta_max      27.000
_cell_measurement_temperature    296(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2016
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_T_max  0.955
_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.70
_diffrn_reflns_number            38623
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.362
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total             10150
_reflns_number_gt                6744
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1200
_refine_ls_wR_factor_gt          0.1013
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.067
_refine_ls_number_reflns         10150
_refine_ls_number_parameters     634
_refine_ls_number_restraints     5
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0483P)²+1.4104P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000


_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;


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
S1 S 0.29583(4) 0.09465(3) -0.05992(3) 0.05319(16) Uani 1 1 d . . . . .
O1 O 0.38546(11) -0.29623(8) 0.34935(8) 0.0592(4) Uani 1 1 d . . . . .
O2 O 0.22971(11) -0.30168(8) 0.28176(8) 0.0514(4) Uani 1 1 d . . . . .
O3 O 0.45688(10) -0.10847(8) 0.25288(8) 0.0516(4) Uani 1 1 d . . . . .
O4 O 0.48321(11) 0.39569(8) -0.03421(9) 0.0610(4) Uani 1 1 d . . . . .
N1 N 0.47958(12) 0.04083(8) 0.11635(8) 0.0413(4) Uani 1 1 d . . . . .
N2 N 0.41309(12) 0.03813(8) 0.05189(8) 0.0449(4) Uani 1 1 d . . . . .
H2 H 0.3929 -0.0032 0.0333 0.054 Uiso 1 1 calc R U . . .
N3 N 0.41647(12) 0.16182(8) 0.04894(8) 0.0426(4) Uani 1 1 d . . . . .
H3A H 0.4658 0.1591 0.0856 0.051 Uiso 1 1 calc R U . . .
C1 C 0.32264(15) -0.26756(11) 0.30359(11) 0.0425(5) Uani 1 1 d . . . . .
C2 C 0.15129(15) -0.27212(11) 0.23135(10) 0.0427(5) Uani 1 1 d . . . . .
C3 C 0.05785(16) -0.30819(12) 0.21744(12) 0.0552(6) Uani 1 1 d . . . . .
H3 H 0.0493 -0.3509 0.2409 0.066 Uiso 1 1 calc R U . . .
C4 C -0.02241(17) -0.27974(13) 0.16821(13) 0.0590(6) Uani 1 1 d . . . . .
H4 H -0.0861 -0.3033 0.1586 0.071 Uiso 1 1 calc R U . . .
C5 C -0.00998(17) -0.21700(13) 0.13297(13) 0.0621(6) Uani 1 1 d . . . . .
H5 H -0.0650 -0.1985 0.0996 0.075 Uiso 1 1 calc R U . . .
C6 C 0.08381(18) -0.18140(13) 0.14694(13) 0.0610(6) Uani 1 1 d . . . . .
H6 H 0.0920 -0.1390 0.1228 0.073 Uiso 1 1 calc R U . . .
C7 C 0.16693(15) -0.20871(11) 0.19732(11) 0.0451(5) Uani 1 1 d . . . . .
C8 C 0.26580(16) -0.17311(11) 0.21783(11) 0.0488(5) Uani 1 1 d . . . . .
H8 H 0.2784 -0.1307 0.1952 0.059 Uiso 1 1 calc R U . . .
C9 C 0.33962(15) -0.20030(11) 0.26899(10) 0.0413(5) Uani 1 1 d . . . . .
C10 C 0.44306(15) -0.16648(11) 0.29727(11) 0.0465(5) Uani 1 1 d . . . . .
H10A H 0.4465 -0.1484 0.3441 0.056 Uiso 1 1 calc R U . . .
H10B H 0.4973 -0.2024 0.2992 0.056 Uiso 1 1 calc R U . . .
C11 C 0.54947(14) -0.07190(10) 0.26842(10) 0.0398(5) Uani 1 1 d . . . . .
C12 C 0.62356(15) -0.08083(11) 0.32981(11) 0.0468(5) Uani 1 1 d . . . . .
H12 H 0.6138 -0.1146 0.3630 0.056 Uiso 1 1 calc R U . . .
C13 C 0.71219(16) -0.03874(12) 0.34091(12) 0.0535(6) Uani 1 1 d . . . . .
H13 H 0.7625 -0.0448 0.3818 0.064 Uiso 1 1 calc R U . . .
C14 C 0.72710(16) 0.01173(12) 0.29264(13) 0.0562(6) Uani 1 1 d . . . . .
H14 H 0.7862 0.0406 0.3014 0.067 Uiso 1 1 calc R U . . .
C15 C 0.65415(15) 0.01959(11) 0.23098(11) 0.0469(5) Uani 1 1 d . . . . .
H15 H 0.6647 0.0536 0.1981 0.056 Uiso 1 1 calc R U . . .
C16 C 0.56509(14) -0.02293(10) 0.21755(10) 0.0385(4) Uani 1 1 d . . . . .
C17 C 0.49093(14) -0.01832(10) 0.15083(10) 0.0413(5) Uani 1 1 d . . . . .
H17 H 0.4517 -0.0589 0.1333 0.050 Uiso 1 1 calc R U . . .
C18 C 0.37954(14) 0.10001(10) 0.01788(10) 0.0381(4) Uani 1 1 d . . . . .
C19 C 0.37939(14) 0.23212(10) 0.02523(10) 0.0394(4) Uani 1 1 d . . . . .
C20 C 0.27695(15) 0.25049(12) 0.02177(12) 0.0527(6) Uani 1 1 d . . . . .
H20 H 0.2321 0.2174 0.0355 0.063 Uiso 1 1 calc R U . . .
C21 C 0.24265(17) 0.31851(13) -0.00230(13) 0.0600(6) Uani 1 1 d . . . . .
H21 H 0.1737 0.3309 -0.0055 0.072 Uiso 1 1 calc R U . . .
C22 C 0.30853(16) 0.36846(12) -0.02178(12) 0.0539(6) Uani 1 1 d . . . . .
H22 H 0.2842 0.4141 -0.0382 0.065 Uiso 1 1 calc R U . . .
C23 C 0.41037(15) 0.35031(10) -0.01683(11) 0.0436(5) Uani 1 1 d . . . . .
C24 C 0.44617(14) 0.28178(10) 0.00710(10) 0.0399(5) Uani 1 1 d . . . . .
H24 H 0.5153 0.2696 0.0108 0.048 Uiso 1 1 calc R U . . .
C25 C 0.4472(2) 0.45639(13) -0.07729(15) 0.0728(7) Uani 1 1 d . . . . .
H25A H 0.3987 0.4403 -0.1183 0.109 Uiso 1 1 calc R U . . .
H25B H 0.5046 0.4799 -0.0906 0.109 Uiso 1 1 calc R U . . .
H25C H 0.4137 0.4901 -0.0521 0.109 Uiso 1 1 calc R U . . .
S2 S 0.67329(4) 0.13397(3) -0.01110(3) 0.05268(16) Uani 1 1 d . . . . .
O5 O 0.90139(11) -0.30144(7) 0.36770(8) 0.0556(4) Uani 1 1 d . . . . .
O6 O 0.74244(11) -0.32122(7) 0.30859(8) 0.0487(4) Uani 1 1 d . . . . .
O7 O 0.92207(9) -0.10619(7) 0.26497(7) 0.0439(3) Uani 1 1 d . . . . .
O8 O 1.00418(11) 0.38501(8) -0.02746(9) 0.0610(4) Uani 1 1 d . . . . .
N4 N 0.89303(11) 0.06942(8) 0.14337(8) 0.0356(4) Uani 1 1 d . . . . .
N5 N 0.80263(11) 0.07436(8) 0.09346(8) 0.0382(4) Uani 1 1 d . . . . .
H5A H 0.7597 0.0386 0.0876 0.046 Uiso 1 1 calc R U . . .
N6 N 0.84820(11) 0.18931(8) 0.06882(8) 0.0386(4) Uani 1 1 d . . . . .
H6A H 0.9031 0.1812 0.1006 0.046 Uiso 1 1 calc R U . . .
C26 C 0.82977(15) -0.27933(10) 0.32324(11) 0.0410(5) Uani 1 1 d . . . . .
C27 C 0.65758(15) -0.30228(10) 0.25683(11) 0.0419(5) Uani 1 1 d . . . . .
C28 C 0.57237(17) -0.34746(12) 0.24756(12) 0.0539(6) Uani 1 1 d . . . . .
H28 H 0.5725 -0.3884 0.2754 0.065 Uiso 1 1 calc R U . . .
C29 C 0.48709(17) -0.33039(13) 0.19598(13) 0.0574(6) Uani 1 1 d . . . . .
H29 H 0.4291 -0.3603 0.1890 0.069 Uiso 1 1 calc R U . . .
C30 C 0.48629(16) -0.26950(13) 0.15436(12) 0.0540(6) Uani 1 1 d . . . . .
H30 H 0.4282 -0.2588 0.1196 0.065 Uiso 1 1 calc R U . . .
C31 C 0.57139(15) -0.22498(12) 0.16452(11) 0.0480(5) Uani 1 1 d . . . . .
H31 H 0.5708 -0.1842 0.1364 0.058 Uiso 1 1 calc R U . . .
C32 C 0.65924(14) -0.24039(10) 0.21680(10) 0.0395(4) Uani 1 1 d . . . . .
C33 C 0.74967(14) -0.19481(10) 0.23314(10) 0.0400(4) Uani 1 1 d . . . . .
H33 H 0.7519 -0.1524 0.2076 0.048 Uiso 1 1 calc R U . . .
C34 C 0.83044(14) -0.21227(10) 0.28427(10) 0.0372(4) Uani 1 1 d . . . . .
C35 C 0.92769(14) -0.16911(10) 0.30725(11) 0.0422(5) Uani 1 1 d . . . . .
H35A H 0.9359 -0.1551 0.3558 0.051 Uiso 1 1 calc R U . . .
H35B H 0.9870 -0.1983 0.3029 0.051 Uiso 1 1 calc R U . . .
C36 C 1.00936(13) -0.06426(10) 0.27353(10) 0.0352(4) Uani 1 1 d . . . . .
C37 C 1.10018(15) -0.07829(11) 0.32243(11) 0.0446(5) Uani 1 1 d . . . . .
H37 H 1.1042 -0.1178 0.3525 0.054 Uiso 1 1 calc R U . . .
C38 C 1.18412(15) -0.03335(12) 0.32607(12) 0.0530(6) Uani 1 1 d . . . . .
H38 H 1.2450 -0.0429 0.3587 0.064 Uiso 1 1 calc R U . . .
C39 C 1.17957(16) 0.02551(12) 0.28228(13) 0.0559(6) Uani 1 1 d . . . . .
H39 H 1.2370 0.0555 0.2853 0.067 Uiso 1 1 calc R U . . .
C40 C 1.08909(14) 0.03988(11) 0.23380(11) 0.0448(5) Uani 1 1 d . . . . .
H40 H 1.0862 0.0797 0.2042 0.054 Uiso 1 1 calc R U . . .
C41 C 1.00241(13) -0.00409(9) 0.22857(10) 0.0343(4) Uani 1 1 d . . . . .
C42 C 0.90745(14) 0.00938(10) 0.17659(10) 0.0359(4) Uani 1 1 d . . . . .
H42 H 0.8566 -0.0264 0.1675 0.043 Uiso 1 1 calc R U . . .
C43 C 0.78013(14) 0.13439(10) 0.05357(10) 0.0354(4) Uani 1 1 d . . . . .
C44 C 0.83843(13) 0.25919(10) 0.03776(10) 0.0362(4) Uani 1 1 d . . . . .
C45 C 0.74711(15) 0.29841(11) 0.02983(12) 0.0464(5) Uani 1 1 d . . . . .
H45 H 0.6910 0.2793 0.0452 0.056 Uiso 1 1 calc R U . . .
C46 C 0.74053(16) 0.36579(11) -0.00092(13) 0.0545(6) Uani 1 1 d . . . . .
H46 H 0.6785 0.3914 -0.0076 0.065 Uiso 1 1 calc R U . . .
C47 C 0.82354(15) 0.39647(11) -0.02208(12) 0.0514(6) Uani 1 1 d . . . . .
H47 H 0.8177 0.4421 -0.0430 0.062 Uiso 1 1 calc R U . . .
C48 C 0.91535(14) 0.35836(10) -0.01168(11) 0.0417(5) Uani 1 1 d . . . . .
C49 C 0.92241(14) 0.28937(10) 0.01756(10) 0.0384(4) Uani 1 1 d . . . . .
H49 H 0.9840 0.2634 0.0235 0.046 Uiso 1 1 calc R U . . .
C50 C 0.99546(19) 0.44226(13) -0.07669(14) 0.0665(7) Uani 1 1 d . . . . .
H50A H 0.9479 0.4284 -0.1190 0.100 Uiso 1 1 calc R U . . .
H50B H 1.0621 0.4520 -0.0864 0.100 Uiso 1 1 calc R U . . .
H50C H 0.9704 0.4852 -0.0580 0.100 Uiso 1 1 calc R U . . .
O9A O 0.0558(2) 0.56574(15) 0.51067(15) 0.0753(7) Uani 0.653(3) 1 d D . P A 1
C51A C -0.0529(8) 0.5609(3) 0.4970(5) 0.0660(15) Uani 0.653(3) 1 d D . P A 1
H51A H -0.0815 0.6067 0.4768 0.079 Uiso 0.653(3) 1 calc R U P A 1
H51B H -0.0736 0.5550 0.5411 0.079 Uiso 0.653(3) 1 calc R U P A 1
C52A C 0.1001(5) 0.4999(4) 0.5511(3) 0.0668(11) Uani 0.653(3) 1 d D . P A 1
H52A H 0.0795 0.4972 0.5955 0.080 Uiso 0.653(3) 1 calc R U P A 1
H52B H 0.1750 0.4994 0.5593 0.080 Uiso 0.653(3) 1 calc R U P A 1
O9B O 0.0080(4) 0.5392(3) 0.5600(3) 0.0753(7) Uani 0.347(3) 1 d D . P A 2
C51B C -0.0426(18) 0.5788(8) 0.5026(11) 0.0660(15) Uani 0.347(3) 1 d D . P A 2
H51C H 0.0034 0.6064 0.4802 0.079 Uiso 0.347(3) 1 calc R U P A 2
H51D H -0.0980 0.6092 0.5118 0.079 Uiso 0.347(3) 1 calc R U P A 2
C52B C -0.0781(10) 0.5109(10) 0.4675(6) 0.0668(11) Uani 0.347(3) 1 d D . P A 2
H52C H -0.1341 0.5232 0.4283 0.080 Uiso 0.347(3) 1 calc R U P A 2
H52D H -0.1085 0.4827 0.4996 0.080 Uiso 0.347(3) 1 calc R U P A 2


_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
S1 C18 1.6816(18) . ?
O1 C1 1.203(2) . ?
O2 C1 1.364(2) . ?
O2 C2 1.379(2) . ?
O3 C11 1.373(2) . ?
O3 C10 1.414(2) . ?
O4 C23 1.374(2) . ?
O4 C25 1.418(3) . ?
N1 C17 1.272(2) . ?
N1 N2 1.375(2) . ?
N2 C18 1.344(2) . ?
N2 H2 0.8600 . ?
N3 C18 1.330(2) . ?
N3 C19 1.423(2) . ?
N3 H3A 0.8600 . ?
C1 C9 1.451(3) . ?
C2 C3 1.377(3) . ?
C2 C7 1.381(3) . ?
C3 C4 1.373(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.401(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.440(3) . ?
C8 C9 1.335(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.496(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.387(3) . ?
C11 C16 1.393(3) . ?
C12 C13 1.382(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.371(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.381(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.391(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.457(2) . ?
C17 H17 0.9300 . ?
C19 C24 1.371(3) . ?
C19 C20 1.385(3) . ?
C20 C21 1.378(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.377(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.372(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.391(3) . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
S2 C43 1.6807(18) . ?
O5 C26 1.209(2) . ?
O6 C26 1.366(2) . ?
O6 C27 1.384(2) . ?
O7 C36 1.369(2) . ?
O7 C35 1.416(2) . ?
O8 C48 1.371(2) . ?
O8 C50 1.416(3) . ?
N4 C42 1.274(2) . ?
N4 N5 1.3734(19) . ?
N5 C43 1.348(2) . ?
N5 H5A 0.8600 . ?
N6 C43 1.342(2) . ?
N6 C44 1.415(2) . ?
N6 H6A 0.8600 . ?
C26 C34 1.452(3) . ?
C27 C28 1.380(3) . ?
C27 C32 1.385(3) . ?
C28 C29 1.377(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.384(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.371(3) . ?
C30 H30 0.9300 . ?
C31 C32 1.401(3) . ?
C31 H31 0.9300 . ?
C32 C33 1.439(3) . ?
C33 C34 1.335(3) . ?
C33 H33 0.9300 . ?
C34 C35 1.495(3) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C37 1.388(2) . ?
C36 C41 1.405(2) . ?
C37 C38 1.374(3) . ?
C37 H37 0.9300 . ?
C38 C39 1.375(3) . ?
C38 H38 0.9300 . ?
C39 C40 1.382(3) . ?
C39 H39 0.9300 . ?
C40 C41 1.389(3) . ?
C40 H40 0.9300 . ?
C41 C42 1.456(2) . ?
C42 H42 0.9300 . ?
C44 C49 1.377(3) . ?
C44 C45 1.387(3) . ?
C45 C46 1.372(3) . ?
C45 H45 0.9300 . ?
C46 C47 1.378(3) . ?
C46 H46 0.9300 . ?
C47 C48 1.379(3) . ?
C47 H47 0.9300 . ?
C48 C49 1.386(3) . ?
C49 H49 0.9300 . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?
O9A C51A 1.408(11) . ?
O9A C52A 1.494(8) . ?
C51A C52A 1.508(7) 3_566 ?
C51A H51A 0.9700 . ?
C51A H51B 0.9700 . ?
C52A C51A 1.508(7) 3_566 ?
C52A H52A 0.9700 . ?
C52A H52B 0.9700 . ?
O9B C51B 1.383(16) . ?
O9B C52B 1.489(18) 3_566 ?
C51B C52B 1.453(14) . ?
C51B H51C 0.9700 . ?
C51B H51D 0.9700 . ?
C52B O9B 1.489(18) 3_566 ?
C52B H52C 0.9700 . ?
C52B H52D 0.9700 . ?

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
C1 O2 C2 121.99(15) . . ?
C11 O3 C10 117.54(14) . . ?
C23 O4 C25 117.59(17) . . ?
C17 N1 N2 115.85(15) . . ?
C18 N2 N1 120.13(15) . . ?
C18 N2 H2 119.9 . . ?
N1 N2 H2 119.9 . . ?
C18 N3 C19 124.00(15) . . ?
C18 N3 H3A 118.0 . . ?
C19 N3 H3A 118.0 . . ?
O1 C1 O2 117.47(18) . . ?
O1 C1 C9 124.70(19) . . ?
O2 C1 C9 117.81(17) . . ?
C3 C2 O2 117.06(18) . . ?
C3 C2 C7 122.26(19) . . ?
O2 C2 C7 120.67(17) . . ?
C4 C3 C2 118.6(2) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C5 C4 C3 121.0(2) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C7 120.3(2) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C2 C7 C6 117.74(19) . . ?
C2 C7 C8 118.15(18) . . ?
C6 C7 C8 124.0(2) . . ?
C9 C8 C7 120.73(19) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C1 120.50(18) . . ?
C8 C9 C10 125.68(19) . . ?
C1 C9 C10 113.81(17) . . ?
O3 C10 C9 108.45(15) . . ?
O3 C10 H10A 110.0 . . ?
C9 C10 H10A 110.0 . . ?
O3 C10 H10B 110.0 . . ?
C9 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
O3 C11 C12 124.21(19) . . ?
O3 C11 C16 115.03(16) . . ?
C12 C11 C16 120.76(18) . . ?
C13 C12 C11 119.0(2) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C14 C13 C12 121.05(19) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 119.8(2) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C16 120.6(2) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 118.71(17) . . ?
C15 C16 C17 120.92(18) . . ?
C11 C16 C17 120.35(17) . . ?
N1 C17 C16 120.38(17) . . ?
N1 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
N3 C18 N2 116.51(16) . . ?
N3 C18 S1 124.68(14) . . ?
N2 C18 S1 118.81(14) . . ?
C24 C19 C20 120.38(18) . . ?
C24 C19 N3 119.54(17) . . ?
C20 C19 N3 120.07(18) . . ?
C21 C20 C19 118.9(2) . . ?
C21 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C22 C21 C20 121.2(2) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C23 C22 C21 119.4(2) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C23 O4 124.61(18) . . ?
C22 C23 C24 120.06(19) . . ?
O4 C23 C24 115.33(17) . . ?
C19 C24 C23 119.93(18) . . ?
C19 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
O4 C25 H25A 109.5 . . ?
O4 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O4 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C26 O6 C27 121.74(15) . . ?
C36 O7 C35 116.99(13) . . ?
C48 O8 C50 118.31(16) . . ?
C42 N4 N5 115.56(14) . . ?
C43 N5 N4 121.03(14) . . ?
C43 N5 H5A 119.5 . . ?
N4 N5 H5A 119.5 . . ?
C43 N6 C44 126.35(15) . . ?
C43 N6 H6A 116.8 . . ?
C44 N6 H6A 116.8 . . ?
O5 C26 O6 117.13(17) . . ?
O5 C26 C34 124.81(18) . . ?
O6 C26 C34 118.06(16) . . ?
C28 C27 O6 117.00(18) . . ?
C28 C27 C32 122.23(19) . . ?
O6 C27 C32 120.77(17) . . ?
C29 C28 C27 118.3(2) . . ?
C29 C28 H28 120.8 . . ?
C27 C28 H28 120.8 . . ?
C28 C29 C30 121.1(2) . . ?
C28 C29 H29 119.4 . . ?
C30 C29 H29 119.4 . . ?
C31 C30 C29 119.8(2) . . ?
C31 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?
C30 C31 C32 120.6(2) . . ?
C30 C31 H31 119.7 . . ?
C32 C31 H31 119.7 . . ?
C27 C32 C31 117.87(17) . . ?
C27 C32 C33 117.88(17) . . ?
C31 C32 C33 124.22(18) . . ?
C34 C33 C32 121.19(18) . . ?
C34 C33 H33 119.4 . . ?
C32 C33 H33 119.4 . . ?
C33 C34 C26 120.24(17) . . ?
C33 C34 C35 126.44(17) . . ?
C26 C34 C35 113.32(16) . . ?
O7 C35 C34 109.00(15) . . ?
O7 C35 H35A 109.9 . . ?
C34 C35 H35A 109.9 . . ?
O7 C35 H35B 109.9 . . ?
C34 C35 H35B 109.9 . . ?
H35A C35 H35B 108.3 . . ?
O7 C36 C37 124.09(17) . . ?
O7 C36 C41 115.40(15) . . ?
C37 C36 C41 120.51(16) . . ?
C38 C37 C36 119.51(19) . . ?
C38 C37 H37 120.2 . . ?
C36 C37 H37 120.2 . . ?
C37 C38 C39 121.10(18) . . ?
C37 C38 H38 119.5 . . ?
C39 C38 H38 119.5 . . ?
C38 C39 C40 119.56(19) . . ?
C38 C39 H39 120.2 . . ?
C40 C39 H39 120.2 . . ?
C39 C40 C41 121.14(19) . . ?
C39 C40 H40 119.4 . . ?
C41 C40 H40 119.4 . . ?
C40 C41 C36 118.18(16) . . ?
C40 C41 C42 121.69(17) . . ?
C36 C41 C42 120.09(15) . . ?
N4 C42 C41 121.00(16) . . ?
N4 C42 H42 119.5 . . ?
C41 C42 H42 119.5 . . ?
N6 C43 N5 115.71(15) . . ?
N6 C43 S2 125.77(14) . . ?
N5 C43 S2 118.50(13) . . ?
C49 C44 C45 119.87(17) . . ?
C49 C44 N6 119.11(16) . . ?
C45 C44 N6 120.98(17) . . ?
C46 C45 C44 119.20(19) . . ?
C46 C45 H45 120.4 . . ?
C44 C45 H45 120.4 . . ?
C45 C46 C47 121.60(18) . . ?
C45 C46 H46 119.2 . . ?
C47 C46 H46 119.2 . . ?
C46 C47 C48 118.91(19) . . ?
C46 C47 H47 120.5 . . ?
C48 C47 H47 120.5 . . ?
O8 C48 C47 123.89(18) . . ?
O8 C48 C49 115.92(16) . . ?
C47 C48 C49 120.18(18) . . ?
C44 C49 C48 120.16(17) . . ?
C44 C49 H49 119.9 . . ?
C48 C49 H49 119.9 . . ?
O8 C50 H50A 109.5 . . ?
O8 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
O8 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C51A O9A C52A 108.4(4) . . ?
O9A C51A C52A 115.6(8) . 3_566 ?
O9A C51A H51A 108.4 . . ?
C52A C51A H51A 108.4 3_566 . ?
O9A C51A H51B 108.4 . . ?
C52A C51A H51B 108.4 3_566 . ?
H51A C51A H51B 107.4 . . ?
O9A C52A C51A 102.0(4) . 3_566 ?
O9A C52A H52A 111.4 . . ?
C51A C52A H52A 111.4 3_566 . ?
O9A C52A H52B 111.4 . . ?
C51A C52A H52B 111.4 3_566 . ?
H52A C52A H52B 109.2 . . ?
C51B O9B C52B 105.0(13) . 3_566 ?
O9B C51B C52B 89.0(10) . . ?
O9B C51B H51C 113.8 . . ?
C52B C51B H51C 113.8 . . ?
O9B C51B H51D 113.8 . . ?
C52B C51B H51D 113.8 . . ?
H51C C51B H51D 111.0 . . ?
C51B C52B O9B 122.7(14) . 3_566 ?
C51B C52B H52C 106.7 . . ?
O9B C52B H52C 106.7 3_566 . ?
C51B C52B H52D 106.7 . . ?
O9B C52B H52D 106.7 3_566 . ?
H52C C52B H52D 106.6 . . ?

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
C17 N1 N2 C18 166.32(19) . . . . ?
C2 O2 C1 O1 177.75(19) . . . . ?
C2 O2 C1 C9 -3.6(3) . . . . ?
C1 O2 C2 C3 -174.76(19) . . . . ?
C1 O2 C2 C7 4.7(3) . . . . ?
O2 C2 C3 C4 179.1(2) . . . . ?
C7 C2 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C4 C5 C6 C7 -0.3(4) . . . . ?
C3 C2 C7 C6 -0.3(3) . . . . ?
O2 C2 C7 C6 -179.6(2) . . . . ?
C3 C2 C7 C8 177.1(2) . . . . ?
O2 C2 C7 C8 -2.3(3) . . . . ?
C5 C6 C7 C2 0.5(4) . . . . ?
C5 C6 C7 C8 -176.6(2) . . . . ?
C2 C7 C8 C9 -0.9(3) . . . . ?
C6 C7 C8 C9 176.3(2) . . . . ?
C7 C8 C9 C1 1.8(3) . . . . ?
C7 C8 C9 C10 -176.8(2) . . . . ?
O1 C1 C9 C8 178.9(2) . . . . ?
O2 C1 C9 C8 0.4(3) . . . . ?
O1 C1 C9 C10 -2.3(3) . . . . ?
O2 C1 C9 C10 179.15(18) . . . . ?
C11 O3 C10 C9 -177.52(17) . . . . ?
C8 C9 C10 O3 -10.4(3) . . . . ?
C1 C9 C10 O3 170.90(17) . . . . ?
C10 O3 C11 C12 -9.9(3) . . . . ?
C10 O3 C11 C16 170.73(18) . . . . ?
O3 C11 C12 C13 -177.36(19) . . . . ?
C16 C11 C12 C13 1.9(3) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C12 C13 C14 C15 -1.8(4) . . . . ?
C13 C14 C15 C16 0.5(3) . . . . ?
C14 C15 C16 C11 2.0(3) . . . . ?
C14 C15 C16 C17 -176.0(2) . . . . ?
O3 C11 C16 C15 176.17(17) . . . . ?
C12 C11 C16 C15 -3.2(3) . . . . ?
O3 C11 C16 C17 -5.8(3) . . . . ?
C12 C11 C16 C17 174.83(18) . . . . ?
N2 N1 C17 C16 175.62(17) . . . . ?
C15 C16 C17 N1 -29.7(3) . . . . ?
C11 C16 C17 N1 152.3(2) . . . . ?
C19 N3 C18 N2 -171.35(18) . . . . ?
C19 N3 C18 S1 9.1(3) . . . . ?
N1 N2 C18 N3 2.0(3) . . . . ?
N1 N2 C18 S1 -178.42(14) . . . . ?
C18 N3 C19 C24 -120.5(2) . . . . ?
C18 N3 C19 C20 60.6(3) . . . . ?
C24 C19 C20 C21 2.1(3) . . . . ?
N3 C19 C20 C21 -179.1(2) . . . . ?
C19 C20 C21 C22 -1.0(4) . . . . ?
C20 C21 C22 C23 -0.3(4) . . . . ?
C21 C22 C23 O4 -179.5(2) . . . . ?
C21 C22 C23 C24 0.6(3) . . . . ?
C25 O4 C23 C22 -18.1(3) . . . . ?
C25 O4 C23 C24 161.8(2) . . . . ?
C20 C19 C24 C23 -1.9(3) . . . . ?
N3 C19 C24 C23 179.31(18) . . . . ?
C22 C23 C24 C19 0.5(3) . . . . ?
O4 C23 C24 C19 -179.40(18) . . . . ?
C42 N4 N5 C43 -178.12(17) . . . . ?
C27 O6 C26 O5 -177.52(18) . . . . ?
C27 O6 C26 C34 2.0(3) . . . . ?
C26 O6 C27 C28 -178.37(19) . . . . ?
C26 O6 C27 C32 1.4(3) . . . . ?
O6 C27 C28 C29 -179.4(2) . . . . ?
C32 C27 C28 C29 0.9(3) . . . . ?
C27 C28 C29 C30 -0.1(4) . . . . ?
C28 C29 C30 C31 -0.3(4) . . . . ?
C29 C30 C31 C32 -0.2(3) . . . . ?
C28 C27 C32 C31 -1.3(3) . . . . ?
O6 C27 C32 C31 178.99(18) . . . . ?
C28 C27 C32 C33 176.66(19) . . . . ?
O6 C27 C32 C33 -3.1(3) . . . . ?
C30 C31 C32 C27 0.9(3) . . . . ?
C30 C31 C32 C33 -176.9(2) . . . . ?
C27 C32 C33 C34 1.4(3) . . . . ?
C31 C32 C33 C34 179.2(2) . . . . ?
C32 C33 C34 C26 1.9(3) . . . . ?
C32 C33 C34 C35 -178.78(19) . . . . ?
O5 C26 C34 C33 175.8(2) . . . . ?
O6 C26 C34 C33 -3.6(3) . . . . ?
O5 C26 C34 C35 -3.6(3) . . . . ?
O6 C26 C34 C35 177.00(17) . . . . ?
C36 O7 C35 C34 -172.98(16) . . . . ?
C33 C34 C35 O7 -1.1(3) . . . . ?
C26 C34 C35 O7 178.31(16) . . . . ?
C35 O7 C36 C37 -2.6(3) . . . . ?
C35 O7 C36 C41 177.28(17) . . . . ?
O7 C36 C37 C38 179.01(19) . . . . ?
C41 C36 C37 C38 -0.8(3) . . . . ?
C36 C37 C38 C39 0.3(3) . . . . ?
C37 C38 C39 C40 0.1(4) . . . . ?
C38 C39 C40 C41 0.1(4) . . . . ?
C39 C40 C41 C36 -0.6(3) . . . . ?
C39 C40 C41 C42 -178.5(2) . . . . ?
O7 C36 C41 C40 -178.85(17) . . . . ?
C37 C36 C41 C40 1.0(3) . . . . ?
O7 C36 C41 C42 -1.0(3) . . . . ?
C37 C36 C41 C42 178.85(18) . . . . ?
N5 N4 C42 C41 177.11(16) . . . . ?
C40 C41 C42 N4 -14.0(3) . . . . ?
C36 C41 C42 N4 168.27(18) . . . . ?
C44 N6 C43 N5 -175.57(17) . . . . ?
C44 N6 C43 S2 6.0(3) . . . . ?
N4 N5 C43 N6 -3.7(3) . . . . ?
N4 N5 C43 S2 174.78(13) . . . . ?
C43 N6 C44 C49 -134.8(2) . . . . ?
C43 N6 C44 C45 47.6(3) . . . . ?
C49 C44 C45 C46 2.8(3) . . . . ?
N6 C44 C45 C46 -179.62(19) . . . . ?
C44 C45 C46 C47 -2.1(3) . . . . ?
C45 C46 C47 C48 -0.3(4) . . . . ?
C50 O8 C48 C47 -21.5(3) . . . . ?
C50 O8 C48 C49 159.7(2) . . . . ?
C46 C47 C48 O8 -176.6(2) . . . . ?
C46 C47 C48 C49 2.1(3) . . . . ?
C45 C44 C49 C48 -1.0(3) . . . . ?
N6 C44 C49 C48 -178.69(17) . . . . ?
O8 C48 C49 C44 177.39(18) . . . . ?
C47 C48 C49 C44 -1.4(3) . . . . ?
C52A O9A C51A C52A -66.3(8) . . . 3_566 ?
C51A O9A C52A C51A 57.6(10) . . . 3_566 ?
C52B O9B C51B C52B 56.3(17) 3_566 . . . ?
O9B C51B C52B O9B -72.7(18) . . . 3_566 ?

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
N2 H2 S2 0.86 2.56 3.3984(16) 164.6 3_655
N3 H3A O1 0.86 2.25 3.027(2) 149.5 2_655
C3 H3 N4 0.93 2.67 3.488(3) 147.3 2_645
C17 H17 S2 0.93 2.94 3.7616(19) 147.7 3_655
N5 H5A S1 0.86 2.58 3.3766(15) 154.6 3_655
N6 H6A O5 0.86 2.55 3.281(2) 143.9 2_755
C42 H42 S1 0.93 2.87 3.6659(18) 144.4 3_655
C49 H49 O5 0.93 2.62 3.316(2) 132.2 2_755
C51B H51D S1 0.97 2.99 3.78(3) 139.4 2
C52B H52D N5 0.97 2.61 3.575(17) 171.3 4_466

_refine_diff_density_max         0.301
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.043

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1036469'
_audit_update_record             
;
2015-03-24 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
(2E)-N-(2,4-dichlorophenyl)-2-{2-[(2-oxo-2H-chromen-3-yl)methoxy]benzylidene}hydrazinecarbothioamide
_chemical_formula_moiety         'C24 H17 Cl2 N3 O3 S'
_chemical_formula_sum            'C24 H17 Cl2 N3 O3 S'
_chemical_formula_iupac          'C24 H17 Cl2 N3 O3 S'
_chemical_formula_weight         498.36

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                   16.0381(11)
_cell_length_b                   9.7005(7)
_cell_length_c                   15.3686(9)
_cell_angle_alpha                90
_cell_angle_beta                 108.349(2)
_cell_angle_gamma                90
_cell_volume                     2269.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3555
_cell_measurement_theta_min      1.338
_cell_measurement_theta_max      27.000
_cell_measurement_temperature    296(2)
_exptl_crystal_description       plate
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.16
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    0.411
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.853
_exptl_absorpt_correction_T_max  0.935
_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.70
_diffrn_reflns_number            19175
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.338
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total             4953
_reflns_number_gt                3555
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1076
_refine_ls_wR_factor_gt          0.0951
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_number_reflns         4953
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0455P)²+0.6380P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;


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
Cl1 Cl -0.25888(4) 0.49891(5) 0.46135(4) 0.05722(16) Uani 1 1 d . . . . .
Cl2 Cl -0.54525(4) 0.74129(6) 0.50074(5) 0.0712(2) Uani 1 1 d . . . . .
S1 S -0.14255(4) 1.03511(6) 0.49144(5) 0.05952(18) Uani 1 1 d . . . . .
O1 O 0.37455(12) 0.54131(18) 0.26368(16) 0.0842(6) Uani 1 1 d . . . . .
O2 O 0.39641(10) 0.76591(16) 0.26188(12) 0.0628(4) Uani 1 1 d . . . . .
O3 O 0.14149(8) 0.58941(13) 0.32259(10) 0.0467(3) Uani 1 1 d . . . . .
N1 N -0.06305(10) 0.70141(17) 0.40184(11) 0.0437(4) Uani 1 1 d . . . . .
N2 N -0.06885(11) 0.83626(17) 0.42591(12) 0.0469(4) Uani 1 1 d . . . . .
H2 H -0.0280 0.8941 0.4265 0.056 Uiso 1 1 calc R U . . .
N3 N -0.20257(10) 0.77956(17) 0.43349(12) 0.0478(4) Uani 1 1 d . . . . .
H3A H -0.1908 0.7056 0.4088 0.057 Uiso 1 1 calc R U . . .
C1 C 0.34688(14) 0.6546(2) 0.27117(17) 0.0562(6) Uani 1 1 d . . . . .
C2 C 0.37136(13) 0.9000(2) 0.27188(15) 0.0498(5) Uani 1 1 d . . . . .
C3 C 0.42600(15) 1.0045(3) 0.26120(17) 0.0618(6) Uani 1 1 d . . . . .
H3 H 0.4777 0.9842 0.2486 0.074 Uiso 1 1 calc R U . . .
C4 C 0.40264(16) 1.1379(3) 0.26947(17) 0.0651(7) Uani 1 1 d . . . . .
H4 H 0.4388 1.2090 0.2622 0.078 Uiso 1 1 calc R U . . .
C5 C 0.32613(16) 1.1689(2) 0.28843(17) 0.0644(6) Uani 1 1 d . . . . .
H5 H 0.3108 1.2603 0.2935 0.077 Uiso 1 1 calc R U . . .
C6 C 0.27253(15) 1.0644(2) 0.29989(16) 0.0573(6) Uani 1 1 d . . . . .
H6 H 0.2213 1.0855 0.3132 0.069 Uiso 1 1 calc R U . . .
C7 C 0.29447(12) 0.9265(2) 0.29163(13) 0.0445(5) Uani 1 1 d . . . . .
C8 C 0.24140(12) 0.8111(2) 0.30079(14) 0.0437(5) Uani 1 1 d . . . . .
H8 H 0.1895 0.8268 0.3141 0.052 Uiso 1 1 calc R U . . .
C9 C 0.26540(12) 0.6821(2) 0.29046(13) 0.0426(4) Uani 1 1 d . . . . .
C10 C 0.21604(13) 0.5537(2) 0.29638(15) 0.0466(5) Uani 1 1 d . . . . .
H10A H 0.1975 0.5075 0.2374 0.056 Uiso 1 1 calc R U . . .
H10B H 0.2536 0.4914 0.3412 0.056 Uiso 1 1 calc R U . . .
C11 C 0.08996(12) 0.48285(19) 0.33450(13) 0.0405(4) Uani 1 1 d . . . . .
C12 C 0.10348(14) 0.3456(2) 0.31774(15) 0.0503(5) Uani 1 1 d . . . . .
H12 H 0.1502 0.3207 0.2975 0.060 Uiso 1 1 calc R U . . .
C13 C 0.04738(15) 0.2461(2) 0.33119(15) 0.0542(5) Uani 1 1 d . . . . .
H13 H 0.0571 0.1540 0.3205 0.065 Uiso 1 1 calc R U . . .
C14 C -0.02267(15) 0.2811(2) 0.36020(15) 0.0553(6) Uani 1 1 d . . . . .
H14 H -0.0606 0.2133 0.3683 0.066 Uiso 1 1 calc R U . . .
C15 C -0.03608(14) 0.4172(2) 0.37707(14) 0.0499(5) Uani 1 1 d . . . . .
H15 H -0.0834 0.4406 0.3969 0.060 Uiso 1 1 calc R U . . .
C16 C 0.01963(12) 0.52084(19) 0.36511(13) 0.0404(4) Uani 1 1 d . . . . .
C17 C 0.00745(12) 0.6644(2) 0.38647(13) 0.0435(5) Uani 1 1 d . . . . .
H17 H 0.0510 0.7290 0.3889 0.052 Uiso 1 1 calc R U . . .
C18 C -0.14034(12) 0.8770(2) 0.44892(13) 0.0422(4) Uani 1 1 d . . . . .
C19 C -0.28361(12) 0.7771(2) 0.45056(13) 0.0428(4) Uani 1 1 d . . . . .
C20 C -0.31705(12) 0.6493(2) 0.46502(14) 0.0432(4) Uani 1 1 d . . . . .
C21 C -0.39694(13) 0.6369(2) 0.48004(15) 0.0494(5) Uani 1 1 d . . . . .
H21 H -0.4180 0.5509 0.4899 0.059 Uiso 1 1 calc R U . . .
C22 C -0.44503(13) 0.7548(2) 0.48016(16) 0.0497(5) Uani 1 1 d . . . . .
C23 C -0.41515(14) 0.8818(2) 0.46316(16) 0.0555(6) Uani 1 1 d . . . . .
H23 H -0.4490 0.9601 0.4617 0.067 Uiso 1 1 calc R U . . .
C24 C -0.33511(13) 0.8928(2) 0.44830(15) 0.0515(5) Uani 1 1 d . . . . .
H24 H -0.3153 0.9789 0.4366 0.062 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
Cl1 C20 1.742(2) . ?
Cl2 C22 1.738(2) . ?
S1 C18 1.672(2) . ?
O1 C1 1.204(3) . ?
O2 C1 1.374(3) . ?
O2 C2 1.384(3) . ?
O3 C11 1.371(2) . ?
O3 C10 1.420(2) . ?
N1 C17 1.277(2) . ?
N1 N2 1.371(2) . ?
N2 C18 1.361(2) . ?
N2 H2 0.8600 . ?
N3 C18 1.341(2) . ?
N3 C19 1.405(2) . ?
N3 H3A 0.8600 . ?
C1 C9 1.453(3) . ?
C2 C3 1.383(3) . ?
C2 C7 1.384(3) . ?
C3 C4 1.364(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.399(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.439(3) . ?
C8 C9 1.333(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.494(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.386(3) . ?
C11 C16 1.401(3) . ?
C12 C13 1.379(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.375(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.395(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.458(3) . ?
C17 H17 0.9300 . ?
C19 C24 1.387(3) . ?
C19 C20 1.396(3) . ?
C20 C21 1.377(3) . ?
C21 C22 1.380(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.377(3) . ?
C23 C24 1.377(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?

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
C1 O2 C2 121.96(15) . . ?
C11 O3 C10 116.78(14) . . ?
C17 N1 N2 117.22(16) . . ?
C18 N2 N1 118.81(15) . . ?
C18 N2 H2 120.6 . . ?
N1 N2 H2 120.6 . . ?
C18 N3 C19 131.28(17) . . ?
C18 N3 H3A 114.4 . . ?
C19 N3 H3A 114.4 . . ?
O1 C1 O2 117.68(18) . . ?
O1 C1 C9 124.7(2) . . ?
O2 C1 C9 117.61(18) . . ?
C3 C2 C7 122.1(2) . . ?
C3 C2 O2 117.31(19) . . ?
C7 C2 O2 120.56(18) . . ?
C4 C3 C2 118.8(2) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 121.0(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 120.0(2) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 120.5(2) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C2 C7 C6 117.67(19) . . ?
C2 C7 C8 118.20(18) . . ?
C6 C7 C8 124.12(18) . . ?
C9 C8 C7 121.08(17) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C1 120.57(18) . . ?
C8 C9 C10 126.65(17) . . ?
C1 C9 C10 112.78(17) . . ?
O3 C10 C9 108.87(15) . . ?
O3 C10 H10A 109.9 . . ?
C9 C10 H10A 109.9 . . ?
O3 C10 H10B 109.9 . . ?
C9 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
O3 C11 C12 124.27(17) . . ?
O3 C11 C16 115.41(16) . . ?
C12 C11 C16 120.31(17) . . ?
C13 C12 C11 119.79(19) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C14 C13 C12 121.0(2) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 119.33(19) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C14 C15 C16 121.5(2) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C15 C16 C11 118.11(18) . . ?
C15 C16 C17 121.47(18) . . ?
C11 C16 C17 120.39(16) . . ?
N1 C17 C16 119.94(17) . . ?
N1 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
N3 C18 N2 112.98(17) . . ?
N3 C18 S1 127.58(15) . . ?
N2 C18 S1 119.44(14) . . ?
C24 C19 C20 117.83(17) . . ?
C24 C19 N3 124.08(18) . . ?
C20 C19 N3 117.96(17) . . ?
C21 C20 C19 121.93(18) . . ?
C21 C20 Cl1 117.91(15) . . ?
C19 C20 Cl1 120.14(15) . . ?
C20 C21 C22 118.54(19) . . ?
C20 C21 H21 120.7 . . ?
C22 C21 H21 120.7 . . ?
C23 C22 C21 120.89(19) . . ?
C23 C22 Cl2 119.93(16) . . ?
C21 C22 Cl2 119.17(16) . . ?
C22 C23 C24 120.0(2) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 C19 120.77(19) . . ?
C23 C24 H24 119.6 . . ?
C19 C24 H24 119.6 . . ?

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
C17 N1 N2 C18 -175.53(18) . . . . ?
C2 O2 C1 O1 -178.2(2) . . . . ?
C2 O2 C1 C9 1.1(3) . . . . ?
C1 O2 C2 C3 180.0(2) . . . . ?
C1 O2 C2 C7 -0.1(3) . . . . ?
C7 C2 C3 C4 -0.7(4) . . . . ?
O2 C2 C3 C4 179.2(2) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C4 C5 C6 C7 -0.6(4) . . . . ?
C3 C2 C7 C6 0.6(3) . . . . ?
O2 C2 C7 C6 -179.3(2) . . . . ?
C3 C2 C7 C8 179.5(2) . . . . ?
O2 C2 C7 C8 -0.4(3) . . . . ?
C5 C6 C7 C2 0.1(3) . . . . ?
C5 C6 C7 C8 -178.8(2) . . . . ?
C2 C7 C8 C9 -0.1(3) . . . . ?
C6 C7 C8 C9 178.8(2) . . . . ?
C7 C8 C9 C1 1.1(3) . . . . ?
C7 C8 C9 C10 -178.8(2) . . . . ?
O1 C1 C9 C8 177.6(2) . . . . ?
O2 C1 C9 C8 -1.6(3) . . . . ?
O1 C1 C9 C10 -2.5(4) . . . . ?
O2 C1 C9 C10 178.33(19) . . . . ?
C11 O3 C10 C9 -177.81(16) . . . . ?
C8 C9 C10 O3 -4.8(3) . . . . ?
C1 C9 C10 O3 175.34(18) . . . . ?
C10 O3 C11 C12 -3.7(3) . . . . ?
C10 O3 C11 C16 176.71(17) . . . . ?
O3 C11 C12 C13 -179.49(19) . . . . ?
C16 C11 C12 C13 0.1(3) . . . . ?
C11 C12 C13 C14 0.7(3) . . . . ?
C12 C13 C14 C15 -0.8(3) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C14 C15 C16 C11 0.5(3) . . . . ?
C14 C15 C16 C17 -177.5(2) . . . . ?
O3 C11 C16 C15 178.95(17) . . . . ?
C12 C11 C16 C15 -0.6(3) . . . . ?
O3 C11 C16 C17 -3.0(3) . . . . ?
C12 C11 C16 C17 177.41(19) . . . . ?
N2 N1 C17 C16 176.91(17) . . . . ?
C15 C16 C17 N1 -11.8(3) . . . . ?
C11 C16 C17 N1 170.20(18) . . . . ?
C19 N3 C18 N2 177.24(19) . . . . ?
C19 N3 C18 S1 -2.8(3) . . . . ?
N1 N2 C18 N3 -7.9(3) . . . . ?
N1 N2 C18 S1 172.09(14) . . . . ?
C18 N3 C19 C24 31.4(3) . . . . ?
C18 N3 C19 C20 -152.9(2) . . . . ?
C24 C19 C20 C21 -2.4(3) . . . . ?
N3 C19 C20 C21 -178.41(18) . . . . ?
C24 C19 C20 Cl1 175.90(16) . . . . ?
N3 C19 C20 Cl1 -0.2(3) . . . . ?
C19 C20 C21 C22 0.4(3) . . . . ?
Cl1 C20 C21 C22 -177.93(16) . . . . ?
C20 C21 C22 C23 1.8(3) . . . . ?
C20 C21 C22 Cl2 -179.03(16) . . . . ?
C21 C22 C23 C24 -1.8(4) . . . . ?
Cl2 C22 C23 C24 178.97(18) . . . . ?
C22 C23 C24 C19 -0.2(4) . . . . ?
C20 C19 C24 C23 2.3(3) . . . . ?
N3 C19 C24 C23 178.1(2) . . . . ?

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
N2 H2 S1 0.86 2.72 3.4576(17) 145.3 3_576
N3 H3A Cl1 0.86 2.53 2.9418(17) 110.1 .
N3 H3A N1 0.86 2.09 2.550(2) 113.2 .
C3 H3 O1 0.93 2.50 3.358(3) 153.9 2_655
C17 H17 S1 0.93 3.01 3.762(2) 138.7 3_576
C21 H21 Cl2 0.93 2.91 3.818(2) 166.4 3_466
C23 H23 Cl2 0.93 2.96 3.782(2) 148.0 3_476
C24 H24 S1 0.93 2.69 3.255(2) 120.2 .

_refine_diff_density_max         0.212
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.041

_shelxl_version_number           2014/6

