# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_cis-4
_database_code_depnum_ccdc_archive 'CCDC 1892457'
loop_
_audit_author_name
_audit_author_address
'Wei Huang' 'Nanjing University'
_audit_update_record             
;
2019-01-22 deposited with the CCDC.	2019-12-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H20 Cl N5 O2 S'
_chemical_formula_sum            'C23 H20 Cl N5 O2 S'
_chemical_formula_weight         465.95

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                   5.093(4)
_cell_length_b                   18.689(15)
_cell_length_c                   24.05(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.684(10)
_cell_angle_gamma                90
_cell_volume                     2284(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    663
_cell_measurement_theta_min      2.339
_cell_measurement_theta_max      17.750

_exptl_crystal_description       needle
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.289
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_process_details   'SADABS, Bruker(2000)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'BRUKER Smart Apex CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16398
_diffrn_reflns_av_unetI/netI     0.2105
_diffrn_reflns_av_R_equivalents  0.1714
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.697
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3995
_reflns_number_gt                1349
_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       'SMART (BRUKER 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (BRUKER 2000)'
_computing_structure_solution    'SHELXTL (BRUKER 2000)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0503P)²+0.8900P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3995
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2352
_refine_ls_R_factor_gt           0.0988
_refine_ls_wR_factor_ref         0.2838
_refine_ls_wR_factor_gt          0.2219
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_restrained_S_all      0.907
_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 1.3841(13) 0.2809(4) 0.2935(2) 0.0836(18) Uani 1 1 d . . . . .
C2 C 1.4008(14) 0.2083(5) 0.2862(2) 0.090(2) Uani 1 1 d . . . . .
C3 C 1.2392(13) 0.1668(4) 0.3177(2) 0.0788(17) Uani 1 1 d . . . . .
C4 C 1.0878(14) 0.2073(3) 0.3501(2) 0.0772(17) Uani 1 1 d . . . . .
C5 C 1.5231(15) 0.3345(5) 0.2640(3) 0.097(2) Uani 1 1 d . . . . .
H5 H 1.6240 0.3183 0.2357 0.117 Uiso 1 1 calc R U . . .
C6 C 1.5224(18) 0.4024(5) 0.2727(3) 0.112(3) Uani 1 1 d . . . . .
H6 H 1.6135 0.4291 0.2476 0.134 Uiso 1 1 calc R U . . .
C7 C 1.4025(19) 0.4444(4) 0.3154(3) 0.108(2) Uani 1 1 d . . . . .
C8 C 1.4887(18) 0.4384(5) 0.3716(3) 0.116(3) Uani 1 1 d . . . . .
H8 H 1.6247 0.4069 0.3818 0.140 Uiso 1 1 calc R U . . .
C9 C 1.380(2) 0.4772(6) 0.4111(4) 0.136(3) Uani 1 1 d . . . . .
H9 H 1.4394 0.4724 0.4483 0.163 Uiso 1 1 calc R U . . .
C10 C 1.181(3) 0.5233(5) 0.3965(5) 0.134(3) Uani 1 1 d . . . . .
C11 C 1.091(2) 0.5313(5) 0.3418(5) 0.139(3) Uani 1 1 d . . . . .
H11 H 0.9535 0.5624 0.3321 0.166 Uiso 1 1 calc R U . . .
C12 C 1.207(2) 0.4929(5) 0.3019(4) 0.126(3) Uani 1 1 d . . . . .
H12 H 1.1525 0.4998 0.2646 0.152 Uiso 1 1 calc R U . . .
C13 C 1.2303(15) 0.0906(5) 0.3177(3) 0.097(2) Uani 1 1 d . . . . .
C14 C 0.6155(14) 0.2076(4) 0.4471(2) 0.0768(17) Uani 1 1 d . . . . .
C15 C 0.5532(15) 0.1370(4) 0.4577(3) 0.094(2) Uani 1 1 d . . . . .
H15 H 0.6327 0.1007 0.4384 0.113 Uiso 1 1 calc R U . . .
C16 C 0.3832(15) 0.1205(4) 0.4947(3) 0.094(2) Uani 1 1 d . . . . .
H16 H 0.3486 0.0724 0.5008 0.113 Uiso 1 1 calc R U . . .
C17 C 0.2512(14) 0.1717(4) 0.5255(3) 0.0888(19) Uani 1 1 d . . . . .
C18 C 0.3110(15) 0.2429(4) 0.5140(3) 0.092(2) Uani 1 1 d . . . . .
H18 H 0.2279 0.2793 0.5325 0.110 Uiso 1 1 calc R U . . .
C19 C 0.4874(13) 0.2601(4) 0.4763(3) 0.0827(18) Uani 1 1 d . . . . .
H19 H 0.5238 0.3080 0.4698 0.099 Uiso 1 1 calc R U . . .
C20 C 0.027(2) 0.0783(5) 0.5778(4) 0.136(3) Uani 1 1 d . . . . .
H20A H -0.1344 0.0761 0.5969 0.164 Uiso 1 1 calc R U . . .
H20B H 0.0024 0.0504 0.5439 0.164 Uiso 1 1 calc R U . . .
C21 C 0.240(2) 0.0464(5) 0.6134(4) 0.146(3) Uani 1 1 d . . . . .
H21A H 0.4039 0.0518 0.5961 0.219 Uiso 1 1 calc R U . . .
H21B H 0.2051 -0.0036 0.6185 0.219 Uiso 1 1 calc R U . . .
H21C H 0.2517 0.0699 0.6490 0.219 Uiso 1 1 calc R U . . .
C22 C -0.0598(16) 0.2083(5) 0.5937(3) 0.122(3) Uani 1 1 d . . . . .
H22A H -0.0965 0.2489 0.5692 0.146 Uiso 1 1 calc R U . . .
H22B H -0.2268 0.1892 0.6041 0.146 Uiso 1 1 calc R U . . .
C23 C 0.093(2) 0.2329(6) 0.6442(3) 0.158(4) Uani 1 1 d . . . . .
H23A H 0.1174 0.1937 0.6698 0.238 Uiso 1 1 calc R U . . .
H23B H -0.0011 0.2707 0.6613 0.238 Uiso 1 1 calc R U . . .
H23C H 0.2608 0.2502 0.6343 0.238 Uiso 1 1 calc R U . . .
Cl1 Cl 1.6032(4) 0.16894(12) 0.24011(7) 0.1127(8) Uani 1 1 d . . . . .
N1 N 0.9147(11) 0.1811(3) 0.3852(2) 0.0797(14) Uani 1 1 d . . . . .
N2 N 0.7929(11) 0.2305(3) 0.4109(2) 0.0800(14) Uani 1 1 d . . . . .
N3 N 1.2307(15) 0.0294(4) 0.3166(3) 0.117(2) Uani 1 1 d . . . . .
N4 N 0.0790(13) 0.1530(4) 0.5632(3) 0.1068(18) Uani 1 1 d . . . . .
N5 N 1.050(3) 0.5681(7) 0.4375(6) 0.184(5) Uani 1 1 d . . . . .
O1 O 1.167(2) 0.5657(5) 0.4854(4) 0.211(4) Uani 1 1 d . . . . .
O2 O 0.861(3) 0.6017(6) 0.4255(6) 0.256(7) Uani 1 1 d . . . . .
S1 S 1.1502(4) 0.29762(9) 0.34130(7) 0.0882(6) 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 C2 1.370(9) . ?
C1 C5 1.439(10) . ?
C1 S1 1.735(7) . ?
C2 C3 1.391(9) . ?
C2 Cl1 1.726(7) . ?
C3 C4 1.361(9) . ?
C3 C13 1.423(11) . ?
C4 N1 1.351(8) . ?
C4 S1 1.732(7) . ?
C5 C6 1.286(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.456(11) . ?
C6 H6 0.9300 . ?
C7 C12 1.369(12) . ?
C7 C8 1.399(10) . ?
C8 C9 1.344(11) . ?
C8 H8 0.9300 . ?
C9 C10 1.356(13) . ?
C9 H9 0.9300 . ?
C10 C11 1.373(12) . ?
C10 N5 1.487(15) . ?
C11 C12 1.362(12) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 N3 1.144(9) . ?
C14 N2 1.363(8) . ?
C14 C15 1.385(9) . ?
C14 C19 1.392(9) . ?
C15 C16 1.317(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.407(9) . ?
C16 H16 0.9300 . ?
C17 N4 1.346(8) . ?
C17 C18 1.398(9) . ?
C18 C19 1.355(9) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.465(11) . ?
C20 N4 1.467(10) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.472(11) . ?
C22 N4 1.474(9) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
N1 N2 1.293(7) . ?
N5 O2 1.170(16) . ?
N5 O1 1.264(15) . ?

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 C5 126.0(7) . . ?
C2 C1 S1 108.3(5) . . ?
C5 C1 S1 125.5(6) . . ?
C1 C2 C3 116.0(6) . . ?
C1 C2 Cl1 123.3(6) . . ?
C3 C2 Cl1 120.7(6) . . ?
C4 C3 C2 112.1(7) . . ?
C4 C3 C13 122.5(7) . . ?
C2 C3 C13 125.3(7) . . ?
N1 C4 C3 124.8(6) . . ?
N1 C4 S1 124.2(5) . . ?
C3 C4 S1 111.0(5) . . ?
C6 C5 C1 126.9(8) . . ?
C6 C5 H5 116.6 . . ?
C1 C5 H5 116.6 . . ?
C5 C6 C7 130.6(8) . . ?
C5 C6 H6 114.7 . . ?
C7 C6 H6 114.7 . . ?
C12 C7 C8 117.3(9) . . ?
C12 C7 C6 121.4(9) . . ?
C8 C7 C6 121.2(9) . . ?
C9 C8 C7 121.5(9) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 119.5(10) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C11 121.0(11) . . ?
C9 C10 N5 123.0(12) . . ?
C11 C10 N5 116.0(13) . . ?
C12 C11 C10 119.0(10) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C7 121.6(9) . . ?
C11 C12 H12 119.2 . . ?
C7 C12 H12 119.2 . . ?
N3 C13 C3 177.6(9) . . ?
N2 C14 C15 125.9(7) . . ?
N2 C14 C19 116.9(6) . . ?
C15 C14 C19 117.2(7) . . ?
C16 C15 C14 121.1(7) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 123.6(7) . . ?
C15 C16 H16 118.2 . . ?
C17 C16 H16 118.2 . . ?
N4 C17 C18 122.7(7) . . ?
N4 C17 C16 122.1(7) . . ?
C18 C17 C16 115.2(6) . . ?
C19 C18 C17 121.4(7) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C18 C19 C14 121.6(7) . . ?
C18 C19 H19 119.2 . . ?
C14 C19 H19 119.2 . . ?
C21 C20 N4 113.0(8) . . ?
C21 C20 H20A 109.0 . . ?
N4 C20 H20A 109.0 . . ?
C21 C20 H20B 109.0 . . ?
N4 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 N4 112.6(7) . . ?
C23 C22 H22A 109.1 . . ?
N4 C22 H22A 109.1 . . ?
C23 C22 H22B 109.1 . . ?
N4 C22 H22B 109.1 . . ?
H22A C22 H22B 107.8 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N2 N1 C4 113.1(6) . . ?
N1 N2 C14 116.1(6) . . ?
C17 N4 C20 122.9(7) . . ?
C17 N4 C22 120.4(7) . . ?
C20 N4 C22 116.7(7) . . ?
O2 N5 O1 125.3(15) . . ?
O2 N5 C10 122.5(16) . . ?
O1 N5 C10 112.2(14) . . ?
C4 S1 C1 92.5(4) . . ?

_refine_diff_density_max         0.421
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.105

####################################################################### 
# 
# 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_trans-4
_database_code_depnum_ccdc_archive 'CCDC 1892458'
loop_
_audit_author_name
_audit_author_address
'Wei Huang' 'Nanjing University'
_audit_update_record             
;
2019-01-22 deposited with the CCDC.	2019-12-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H20 Cl N5 O2 S'
_chemical_formula_sum            'C23 H20 Cl N5 O2 S'
_chemical_formula_weight         465.95

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'
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'
O O 0.0106 0.0060 '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                   10.9364(11)
_cell_length_b                   10.8589(11)
_cell_length_c                   38.833(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.052(2)
_cell_angle_gamma                90
_cell_volume                     4610.9(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    2412
_cell_measurement_theta_min      2.416
_cell_measurement_theta_max      18.608

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             1936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.286
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_process_details   'SADABS, Bruker(2000)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'BRUKER Smart Apex CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33926
_diffrn_reflns_av_unetI/netI     0.0783
_diffrn_reflns_av_R_equivalents  0.0869
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         1.926
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             8049
_reflns_number_gt                4076
_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       'SMART (BRUKER 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (BRUKER 2000)'
_computing_structure_solution    'SHELXTL (BRUKER 2000)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0835P)²+8.8900P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8049
_refine_ls_number_parameters     581
_refine_ls_number_restraints     68
_refine_ls_R_factor_all          0.1599
_refine_ls_R_factor_gt           0.0892
_refine_ls_wR_factor_ref         0.2444
_refine_ls_wR_factor_gt          0.2135
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.010
_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 0.1076(5) 0.9049(5) 0.88948(14) 0.0558(13) Uani 1 1 d . . . . .
C2 C 0.0180(5) 0.9679(5) 0.90675(14) 0.0585(14) Uani 1 1 d . . . . .
C3 C -0.0024(5) 0.9178(5) 0.93946(14) 0.0591(14) Uani 1 1 d . . . . .
C4 C 0.0684(5) 0.8187(5) 0.94763(14) 0.0554(13) Uani 1 1 d . . . . .
C5 C 0.0695(5) 0.7470(5) 0.97875(14) 0.0580(14) Uani 1 1 d . . . . .
H5 H 0.0193 0.7740 0.9963 0.070 Uiso 1 1 calc R U . . .
C6 C 0.1347(5) 0.6463(5) 0.98496(14) 0.0585(14) Uani 1 1 d . . . . .
H6 H 0.1865 0.6218 0.9675 0.070 Uiso 1 1 calc R U . . .
C7 C 0.1355(4) 0.5694(5) 1.01548(14) 0.0556(13) Uani 1 1 d . . . . .
C8 C 0.0715(5) 0.6023(6) 1.04517(15) 0.0711(16) Uani 1 1 d . . . . .
H8 H 0.0271 0.6754 1.0456 0.085 Uiso 1 1 calc R U . . .
C9 C 0.0743(6) 0.5263(6) 1.07384(16) 0.0742(17) Uani 1 1 d . . . . .
H9 H 0.0318 0.5482 1.0934 0.089 Uiso 1 1 calc R U . . .
C10 C 0.1398(5) 0.4185(6) 1.07323(15) 0.0665(15) Uani 1 1 d . . . . .
C11 C 0.2029(5) 0.3843(6) 1.04447(17) 0.0732(17) Uani 1 1 d . . . . .
H11 H 0.2479 0.3116 1.0443 0.088 Uiso 1 1 calc R U . . .
C12 C 0.1983(5) 0.4597(5) 1.01599(15) 0.0642(15) Uani 1 1 d . . . . .
H12 H 0.2393 0.4356 0.9963 0.077 Uiso 1 1 calc R U . . .
C13 C -0.0444(6) 1.0707(7) 0.89324(16) 0.0778(18) Uani 1 1 d . . . . .
C14 C 0.2788(5) 0.8952(6) 0.81504(15) 0.0673(16) Uani 1 1 d . . . . .
C15 C 0.2421(6) 0.9955(6) 0.79512(16) 0.0788(18) Uani 1 1 d . . . . .
H15 H 0.1823 1.0486 0.8032 0.095 Uiso 1 1 calc R U . . .
C16 C 0.2924(7) 1.0166(7) 0.76414(18) 0.093(2) Uani 1 1 d . . . . .
H16 H 0.2672 1.0850 0.7515 0.112 Uiso 1 1 calc R U . . .
C17 C 0.3810(7) 0.9387(7) 0.75060(17) 0.096(2) Uani 1 1 d . . . . .
C18 C 0.4196(7) 0.8381(7) 0.77089(19) 0.104(3) Uani 1 1 d . . . . .
H18 H 0.4796 0.7852 0.7629 0.124 Uiso 1 1 calc R U . . .
C19 C 0.3692(6) 0.8175(6) 0.80239(17) 0.088(2) Uani 1 1 d . . . . .
H19 H 0.3957 0.7508 0.8156 0.105 Uiso 1 1 calc R U . . .
C20 C 0.3828(11) 1.0597(10) 0.6941(3) 0.170(2) Uani 1 1 d D U . . .
H20A H 0.4024 1.0394 0.6705 0.204 Uiso 1 1 calc R U . . .
H20B H 0.2949 1.0689 0.6960 0.204 Uiso 1 1 calc R U . . .
C21 C 0.4451(11) 1.1671(10) 0.7054(3) 0.176(2) Uani 1 1 d D U . . .
H21A H 0.4385 1.1749 0.7299 0.263 Uiso 1 1 calc R U . . .
H21B H 0.4093 1.2380 0.6944 0.263 Uiso 1 1 calc R U . . .
H21C H 0.5298 1.1613 0.6995 0.263 Uiso 1 1 calc R U . . .
C22 C 0.5372(12) 0.8814(10) 0.7065(3) 0.170(2) Uani 1 1 d . U . . .
H22A H 0.5849 0.9252 0.6896 0.204 Uiso 1 1 calc R U . . .
H22B H 0.5908 0.8585 0.7256 0.204 Uiso 1 1 calc R U . . .
C23 C 0.4831(11) 0.7747(10) 0.6915(3) 0.172(2) Uani 1 1 d . U . . .
H23A H 0.4508 0.7234 0.7093 0.258 Uiso 1 1 calc R U . . .
H23B H 0.5438 0.7298 0.6791 0.258 Uiso 1 1 calc R U . . .
H23C H 0.4181 0.7988 0.6759 0.258 Uiso 1 1 calc R U . . .
C24 C 0.4067(5) 0.9658(5) 0.94792(15) 0.0592(14) Uani 1 1 d . . . . .
C25 C 0.3436(5) 1.0624(5) 0.93360(15) 0.0615(14) Uani 1 1 d . . . . .
C26 C 0.3799(5) 1.0883(5) 0.89951(15) 0.0617(14) Uani 1 1 d . . . . .
C27 C 0.4713(5) 1.0136(5) 0.88838(15) 0.0640(15) Uani 1 1 d . . . . .
C28 C 0.5336(6) 1.0210(6) 0.85601(15) 0.0715(16) Uani 1 1 d . . . . .
H28 H 0.4967 1.0691 0.8390 0.086 Uiso 1 1 calc R U . . .
C29 C 0.6380(6) 0.9664(6) 0.84794(16) 0.0824(19) Uani 1 1 d . . . . .
H29 H 0.6723 0.9139 0.8644 0.099 Uiso 1 1 calc R U . . .
C30 C 0.7033(7) 0.9804(8) 0.81623(18) 0.091(2) Uani 1 1 d . . . . .
C31 C 0.8169(7) 0.9241(9) 0.8128(2) 0.115(3) Uani 1 1 d . . . . .
H31 H 0.8468 0.8736 0.8304 0.137 Uiso 1 1 calc R U . . .
C32 C 0.8861(11) 0.9418(14) 0.7837(3) 0.203(3) Uani 1 1 d . U . . .
H32 H 0.9626 0.9053 0.7819 0.244 Uiso 1 1 calc R U . . .
C33 C 0.8417(12) 1.0114(15) 0.7586(3) 0.204(2) Uani 1 1 d . U . . .
C34 C 0.7328(11) 1.0740(14) 0.7599(3) 0.203(3) Uani 1 1 d . U . . .
H34 H 0.7068 1.1254 0.7421 0.244 Uiso 1 1 calc R U . . .
C35 C 0.6636(8) 1.0569(9) 0.7891(2) 0.119(3) Uani 1 1 d . . . . .
H35 H 0.5888 1.0972 0.7907 0.143 Uiso 1 1 calc R U . . .
C36 C 0.2508(6) 1.1306(6) 0.95085(17) 0.0702(16) Uani 1 1 d . . . . .
C37 C 0.4367(5) 0.7598(5) 1.01629(15) 0.0598(14) Uani 1 1 d . . . . .
C38 C 0.5015(5) 0.6516(6) 1.02064(16) 0.0725(17) Uani 1 1 d . . . . .
H38 H 0.5501 0.6237 1.0028 0.087 Uiso 1 1 calc R U . . .
C39 C 0.4965(6) 0.5837(6) 1.05052(17) 0.0803(19) Uani 1 1 d . . . . .
H39 H 0.5415 0.5113 1.0527 0.096 Uiso 1 1 calc R U . . .
C40 C 0.4234(5) 0.6235(6) 1.07786(15) 0.0689(16) Uani 1 1 d . . . . .
C41 C 0.3579(5) 0.7337(6) 1.07304(16) 0.0659(15) Uani 1 1 d . . . . .
H41 H 0.3089 0.7625 1.0906 0.079 Uiso 1 1 calc R U . . .
C42 C 0.3642(5) 0.7993(5) 1.04336(15) 0.0639(15) Uani 1 1 d . . . . .
H42 H 0.3195 0.8718 1.0410 0.077 Uiso 1 1 calc R U . . .
C43 C 0.4755(9) 0.4326(8) 1.1109(2) 0.1130(15) Uani 1 1 d . U . . .
H43A H 0.4323 0.3832 1.1276 0.136 Uiso 1 1 calc R U . . .
H43B H 0.4720 0.3900 1.0890 0.136 Uiso 1 1 calc R U . . .
C44 C 0.6032(10) 0.4468(10) 1.1221(3) 0.158(4) Uani 1 1 d . . . . .
H44A H 0.6451 0.4984 1.1061 0.237 Uiso 1 1 calc R U . . .
H44B H 0.6418 0.3674 1.1231 0.237 Uiso 1 1 calc R U . . .
H44C H 0.6064 0.4838 1.1446 0.237 Uiso 1 1 calc R U . . .
C45 C 0.3214(8) 0.5855(8) 1.1360(2) 0.1136(15) Uani 1 1 d D U . . .
H45A H 0.2479 0.6231 1.1264 0.136 Uiso 1 1 calc R U . . .
H45B H 0.2992 0.5116 1.1485 0.136 Uiso 1 1 calc R U . . .
C46 C 0.3847(10) 0.6675(9) 1.1574(3) 0.175(5) Uani 1 1 d D . . . .
H46A H 0.4613 0.6316 1.1645 0.262 Uiso 1 1 calc R U . . .
H46B H 0.3369 0.6848 1.1773 0.262 Uiso 1 1 calc R U . . .
H46C H 0.3994 0.7426 1.1451 0.262 Uiso 1 1 calc R U . . .
Cl1 Cl -0.11368(15) 0.97377(16) 0.96585(4) 0.0847(5) Uani 1 1 d . . . . .
Cl2 Cl 0.31526(15) 1.20368(16) 0.87544(5) 0.0847(5) Uani 1 1 d . . . . .
N1 N 0.1467(4) 0.9361(4) 0.85733(12) 0.0641(12) Uani 1 1 d . . . . .
N2 N 0.2335(4) 0.8658(4) 0.84693(12) 0.0655(12) Uani 1 1 d . . . . .
N3 N -0.0976(6) 1.1553(6) 0.88286(15) 0.106(2) Uani 1 1 d . . . . .
N4 N 0.4322(9) 0.9631(8) 0.7192(2) 0.169(2) Uani 1 1 d . U . . .
N5 N 0.1438(6) 0.3403(6) 1.10385(16) 0.0854(16) Uani 1 1 d . . . . .
N6 N 0.3857(4) 0.9162(4) 0.97983(12) 0.0600(12) Uani 1 1 d . . . . .
N7 N 0.4493(4) 0.8177(4) 0.98460(12) 0.0637(12) Uani 1 1 d . . . . .
N8 N 0.1774(5) 1.1908(5) 0.96296(16) 0.0952(18) Uani 1 1 d . . . . .
N9 N 0.4144(6) 0.5561(6) 1.10734(16) 0.1124(15) Uani 1 1 d . U . . .
N10 N 0.9151(10) 1.0413(14) 0.7291(2) 0.206(2) Uani 1 1 d . U . . .
O1 O 0.2063(6) 0.2466(6) 1.10257(15) 0.1189(19) Uani 1 1 d . . . . .
O2 O 0.0849(6) 0.3706(6) 1.12857(14) 0.1195(19) Uani 1 1 d . . . . .
O3 O 1.0036(8) 1.0014(10) 0.72395(17) 0.211(3) Uani 1 1 d . U . . .
O4 O 0.8736(8) 1.1090(11) 0.70508(19) 0.210(3) Uani 1 1 d . U . . .
S1 S 0.16647(12) 0.78544(13) 0.91392(4) 0.0605(4) Uani 1 1 d . . . . .
S2 S 0.51281(14) 0.90677(14) 0.91974(4) 0.0677(4) 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 N1 1.369(6) . ?
C1 C2 1.379(7) . ?
C1 S1 1.725(6) . ?
C2 C3 1.404(7) . ?
C2 C13 1.405(9) . ?
C3 C4 1.360(7) . ?
C3 Cl1 1.716(5) . ?
C4 C5 1.437(7) . ?
C4 S1 1.745(5) . ?
C5 C6 1.325(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.449(7) . ?
C6 H6 0.9300 . ?
C7 C12 1.375(7) . ?
C7 C8 1.406(7) . ?
C8 C9 1.386(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.372(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.375(8) . ?
C10 N5 1.462(8) . ?
C11 C12 1.376(8) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 N3 1.156(8) . ?
C14 N2 1.380(7) . ?
C14 C15 1.391(8) . ?
C14 C19 1.396(8) . ?
C15 C16 1.351(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.397(9) . ?
C16 H16 0.9300 . ?
C17 N4 1.377(9) . ?
C17 C18 1.407(10) . ?
C18 C19 1.369(8) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.415(8) . ?
C20 N4 1.523(13) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.422(14) . ?
C22 N4 1.539(13) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.367(8) . ?
C24 N6 1.375(7) . ?
C24 S2 1.732(5) . ?
C25 C26 1.417(8) . ?
C25 C36 1.433(8) . ?
C26 C27 1.363(7) . ?
C26 Cl2 1.709(6) . ?
C27 C28 1.443(8) . ?
C27 S2 1.737(6) . ?
C28 C29 1.329(8) . ?
C28 H28 0.9300 . ?
C29 C30 1.443(9) . ?
C29 H29 0.9300 . ?
C30 C31 1.393(10) . ?
C30 C35 1.406(11) . ?
C31 C32 1.386(11) . ?
C31 H31 0.9300 . ?
C32 C33 1.32(2) . ?
C32 H32 0.9300 . ?
C33 C34 1.373(19) . ?
C33 N10 1.447(14) . ?
C34 C35 1.385(11) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C36 N8 1.143(7) . ?
C37 C38 1.381(8) . ?
C37 N7 1.392(7) . ?
C37 C42 1.396(7) . ?
C38 C39 1.377(8) . ?
C38 H38 0.9300 . ?
C39 C40 1.408(8) . ?
C39 H39 0.9300 . ?
C40 N9 1.363(8) . ?
C40 C41 1.406(8) . ?
C41 C42 1.357(8) . ?
C41 H41 0.9300 . ?
C42 H42 0.9300 . ?
C43 C44 1.463(12) . ?
C43 N9 1.504(9) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C45 C46 1.391(8) . ?
C45 N9 1.556(9) . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
N1 N2 1.289(6) . ?
N5 O2 1.212(7) . ?
N5 O1 1.227(7) . ?
N6 N7 1.287(6) . ?
N10 O3 1.082(14) . ?
N10 O4 1.264(16) . ?

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 C2 123.9(5) . . ?
N1 C1 S1 124.6(4) . . ?
C2 C1 S1 111.5(4) . . ?
C1 C2 C3 112.0(5) . . ?
C1 C2 C13 123.9(5) . . ?
C3 C2 C13 124.1(5) . . ?
C4 C3 C2 114.7(5) . . ?
C4 C3 Cl1 123.2(4) . . ?
C2 C3 Cl1 122.0(4) . . ?
C3 C4 C5 128.3(5) . . ?
C3 C4 S1 110.1(4) . . ?
C5 C4 S1 121.5(4) . . ?
C6 C5 C4 126.6(5) . . ?
C6 C5 H5 116.7 . . ?
C4 C5 H5 116.7 . . ?
C5 C6 C7 128.3(5) . . ?
C5 C6 H6 115.9 . . ?
C7 C6 H6 115.9 . . ?
C12 C7 C8 117.7(5) . . ?
C12 C7 C6 120.4(5) . . ?
C8 C7 C6 121.9(5) . . ?
C9 C8 C7 120.2(6) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 119.9(6) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 120.9(6) . . ?
C9 C10 N5 119.3(6) . . ?
C11 C10 N5 119.7(6) . . ?
C10 C11 C12 118.7(6) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C7 C12 C11 122.5(5) . . ?
C7 C12 H12 118.7 . . ?
C11 C12 H12 118.7 . . ?
N3 C13 C2 178.2(7) . . ?
N2 C14 C15 125.2(5) . . ?
N2 C14 C19 116.4(6) . . ?
C15 C14 C19 118.5(5) . . ?
C16 C15 C14 120.6(6) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 122.0(7) . . ?
C15 C16 H16 119.0 . . ?
C17 C16 H16 119.0 . . ?
N4 C17 C16 120.8(8) . . ?
N4 C17 C18 121.6(7) . . ?
C16 C17 C18 117.5(6) . . ?
C19 C18 C17 120.4(6) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C14 121.0(6) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?
C21 C20 N4 102.0(10) . . ?
C21 C20 H20A 111.4 . . ?
N4 C20 H20A 111.4 . . ?
C21 C20 H20B 111.4 . . ?
N4 C20 H20B 111.4 . . ?
H20A C20 H20B 109.2 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 N4 107.1(11) . . ?
C23 C22 H22A 110.3 . . ?
N4 C22 H22A 110.3 . . ?
C23 C22 H22B 110.3 . . ?
N4 C22 H22B 110.3 . . ?
H22A C22 H22B 108.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 N6 125.2(5) . . ?
C25 C24 S2 111.4(4) . . ?
N6 C24 S2 123.3(4) . . ?
C24 C25 C26 112.6(5) . . ?
C24 C25 C36 124.2(5) . . ?
C26 C25 C36 123.2(5) . . ?
C27 C26 C25 113.4(5) . . ?
C27 C26 Cl2 124.1(5) . . ?
C25 C26 Cl2 122.4(4) . . ?
C26 C27 C28 127.2(6) . . ?
C26 C27 S2 111.0(4) . . ?
C28 C27 S2 121.8(4) . . ?
C29 C28 C27 127.0(6) . . ?
C29 C28 H28 116.5 . . ?
C27 C28 H28 116.5 . . ?
C28 C29 C30 126.6(7) . . ?
C28 C29 H29 116.7 . . ?
C30 C29 H29 116.7 . . ?
C31 C30 C35 116.9(7) . . ?
C31 C30 C29 119.4(7) . . ?
C35 C30 C29 123.5(7) . . ?
C32 C31 C30 121.2(10) . . ?
C32 C31 H31 119.4 . . ?
C30 C31 H31 119.4 . . ?
C33 C32 C31 119.0(13) . . ?
C33 C32 H32 120.5 . . ?
C31 C32 H32 120.5 . . ?
C32 C33 C34 124.2(11) . . ?
C32 C33 N10 120.8(14) . . ?
C34 C33 N10 114.4(15) . . ?
C33 C34 C35 116.9(14) . . ?
C33 C34 H34 121.5 . . ?
C35 C34 H34 121.5 . . ?
C34 C35 C30 121.7(11) . . ?
C34 C35 H35 119.1 . . ?
C30 C35 H35 119.1 . . ?
N8 C36 C25 175.5(7) . . ?
C38 C37 N7 115.8(5) . . ?
C38 C37 C42 117.8(6) . . ?
N7 C37 C42 126.4(5) . . ?
C39 C38 C37 122.0(5) . . ?
C39 C38 H38 119.0 . . ?
C37 C38 H38 119.0 . . ?
C38 C39 C40 120.2(6) . . ?
C38 C39 H39 119.9 . . ?
C40 C39 H39 119.9 . . ?
N9 C40 C41 121.6(6) . . ?
N9 C40 C39 121.3(6) . . ?
C41 C40 C39 117.1(6) . . ?
C42 C41 C40 121.7(5) . . ?
C42 C41 H41 119.1 . . ?
C40 C41 H41 119.1 . . ?
C41 C42 C37 121.1(5) . . ?
C41 C42 H42 119.5 . . ?
C37 C42 H42 119.5 . . ?
C44 C43 N9 110.7(8) . . ?
C44 C43 H43A 109.5 . . ?
N9 C43 H43A 109.5 . . ?
C44 C43 H43B 109.5 . . ?
N9 C43 H43B 109.5 . . ?
H43A C43 H43B 108.1 . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C46 C45 N9 103.5(9) . . ?
C46 C45 H45A 111.1 . . ?
N9 C45 H45A 111.1 . . ?
C46 C45 H45B 111.1 . . ?
N9 C45 H45B 111.1 . . ?
H45A C45 H45B 109.0 . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
N2 N1 C1 112.5(5) . . ?
N1 N2 C14 115.0(5) . . ?
C17 N4 C20 123.6(9) . . ?
C17 N4 C22 119.3(8) . . ?
C20 N4 C22 116.8(8) . . ?
O2 N5 O1 124.2(7) . . ?
O2 N5 C10 118.6(7) . . ?
O1 N5 C10 117.2(6) . . ?
N7 N6 C24 110.9(4) . . ?
N6 N7 C37 116.2(5) . . ?
C40 N9 C43 121.2(6) . . ?
C40 N9 C45 123.3(6) . . ?
C43 N9 C45 114.3(6) . . ?
O3 N10 O4 114.1(10) . . ?
O3 N10 C33 124.5(16) . . ?
O4 N10 C33 121.1(13) . . ?
C1 S1 C4 91.7(3) . . ?
C24 S2 C27 91.5(3) . . ?

_refine_diff_density_max         0.861
_refine_diff_density_min         -0.773
_refine_diff_density_rms         0.071

####################################################################### 
# 
# 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_trans-6
_database_code_depnum_ccdc_archive 'CCDC 1892460'
loop_
_audit_author_name
_audit_author_address
'Wei Huang' 'Nanjing University'
_audit_update_record             
;
2019-01-22 deposited with the CCDC.	2019-12-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H21 Cl N4 S'
_chemical_formula_sum            'C23 H21 Cl N4 S'
_chemical_formula_weight         420.95

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'
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                   14.7727(15)
_cell_length_b                   7.6261(8)
_cell_length_c                   19.442(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.253(2)
_cell_angle_gamma                90
_cell_volume                     2181.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    2172
_cell_measurement_theta_min      2.411
_cell_measurement_theta_max      20.773

_exptl_crystal_description       needle
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.287
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_process_details   'SADABS, Bruker(2000)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'BRUKER Smart Apex CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15589
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.104
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3811
_reflns_number_gt                2730
_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       'SMART (BRUKER 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (BRUKER 2000)'
_computing_structure_solution    'SHELXTL (BRUKER 2000)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0822P)²+1.9678P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3811
_refine_ls_number_parameters     264
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0662
_refine_ls_wR_factor_ref         0.1920
_refine_ls_wR_factor_gt          0.1768
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.100
_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 0.1418(2) 0.0840(4) 0.03920(18) 0.0509(9) Uani 1 1 d . . . . .
C2 C 0.1939(2) 0.0865(5) -0.01501(18) 0.0512(8) Uani 1 1 d . . . . .
C3 C 0.2453(2) 0.2417(5) -0.02023(18) 0.0519(9) Uani 1 1 d . . . . .
C4 C 0.2306(2) 0.3597(5) 0.03079(18) 0.0499(8) Uani 1 1 d . . . . .
C5 C 0.0861(2) -0.0584(5) 0.0600(2) 0.0547(9) Uani 1 1 d . . . . .
H5 H 0.0834 -0.1580 0.0323 0.066 Uiso 1 1 calc R U . . .
C6 C 0.0379(3) -0.0623(5) 0.1148(2) 0.0612(10) Uani 1 1 d . . . . .
H6 H 0.0381 0.0386 0.1417 0.073 Uiso 1 1 calc R U . . .
C7 C -0.0151(2) -0.2108(5) 0.1364(2) 0.0583(10) Uani 1 1 d . . . . .
C8 C -0.0661(3) -0.1916(7) 0.1919(2) 0.0800(13) Uani 1 1 d . . . . .
H8 H -0.0650 -0.0853 0.2154 0.096 Uiso 1 1 calc R U . . .
C9 C -0.1193(4) -0.3285(9) 0.2134(3) 0.0986(17) Uani 1 1 d . . . . .
H9 H -0.1537 -0.3136 0.2507 0.118 Uiso 1 1 calc R U . . .
C10 C -0.1205(4) -0.4849(9) 0.1789(3) 0.1014(18) Uani 1 1 d . . . . .
H10 H -0.1560 -0.5768 0.1928 0.122 Uiso 1 1 calc R U . . .
C11 C -0.0699(3) -0.5069(7) 0.1245(3) 0.0929(15) Uani 1 1 d . . . . .
H11 H -0.0707 -0.6138 0.1014 0.112 Uiso 1 1 calc R U . . .
C12 C -0.0173(3) -0.3708(6) 0.1034(3) 0.0765(12) Uani 1 1 d . . . . .
H12 H 0.0172 -0.3875 0.0663 0.092 Uiso 1 1 calc R U . . .
C13 C 0.3078(3) 0.2718(6) -0.0704(2) 0.0731(12) Uani 1 1 d . . . . .
C14 C 0.3012(2) 0.7570(4) 0.10654(18) 0.0487(8) Uani 1 1 d . . . . .
C15 C 0.3664(3) 0.8263(5) 0.06699(18) 0.0582(10) Uani 1 1 d . . . . .
H15 H 0.3798 0.7687 0.0270 0.070 Uiso 1 1 calc R U . . .
C16 C 0.4109(3) 0.9770(5) 0.08591(19) 0.0656(11) Uani 1 1 d . . . . .
H16 H 0.4526 1.0224 0.0576 0.079 Uiso 1 1 calc R U . . .
C17 C 0.3957(3) 1.0668(5) 0.14719(19) 0.0579(9) Uani 1 1 d . . . . .
C18 C 0.3291(2) 0.9962(5) 0.18672(19) 0.0537(9) Uani 1 1 d . . . . .
H18 H 0.3161 1.0518 0.2272 0.064 Uiso 1 1 calc R U . . .
C19 C 0.2833(2) 0.8462(5) 0.16598(18) 0.0511(8) Uani 1 1 d . . . . .
H19 H 0.2389 0.8031 0.1925 0.061 Uiso 1 1 calc R U . . .
C20 C 0.4886(4) 1.3274(8) 0.1133(3) 0.118(2) Uani 1 1 d D U . . .
H20A H 0.4627 1.3038 0.0665 0.142 Uiso 1 1 calc R U . . .
H20B H 0.4840 1.4518 0.1229 0.142 Uiso 1 1 calc R U . . .
C21 C 0.5812(5) 1.2662(9) 0.1246(3) 0.132(2) Uani 1 1 d D U . . .
H21A H 0.6047 1.2920 0.1712 0.198 Uiso 1 1 calc R U . . .
H21B H 0.6177 1.3240 0.0930 0.198 Uiso 1 1 calc R U . . .
H21C H 0.5829 1.1419 0.1171 0.198 Uiso 1 1 calc R U . . .
C22 C 0.4393(3) 1.2888(6) 0.2369(2) 0.0736(12) Uani 1 1 d . . . . .
H22A H 0.4974 1.3422 0.2516 0.088 Uiso 1 1 calc R U . . .
H22B H 0.4287 1.1956 0.2692 0.088 Uiso 1 1 calc R U . . .
C23 C 0.3657(5) 1.4241(7) 0.2387(3) 0.1067(19) Uani 1 1 d . . . . .
H23A H 0.3788 1.5215 0.2099 0.160 Uiso 1 1 calc R U . . .
H23B H 0.3628 1.4638 0.2853 0.160 Uiso 1 1 calc R U . . .
H23C H 0.3084 1.3733 0.2219 0.160 Uiso 1 1 calc R U . . .
Cl1 Cl 0.20183(7) -0.08581(13) -0.07081(5) 0.0702(4) Uani 1 1 d . . . . .
N1 N 0.2751(2) 0.5178(4) 0.03933(15) 0.0532(7) Uani 1 1 d . . . . .
N2 N 0.2538(2) 0.6029(4) 0.09258(15) 0.0523(7) Uani 1 1 d . . . . .
N3 N 0.3580(4) 0.2954(7) -0.1097(3) 0.123(2) Uani 1 1 d . . . . .
N4 N 0.4427(3) 1.2136(5) 0.16746(19) 0.0875(12) Uani 1 1 d D U . . .
S1 S 0.15379(6) 0.27983(12) 0.08519(5) 0.0557(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 C2 1.360(5) . ?
C1 C5 1.443(5) . ?
C1 S1 1.741(3) . ?
C2 C3 1.415(5) . ?
C2 Cl1 1.715(4) . ?
C3 C4 1.371(5) . ?
C3 C13 1.422(5) . ?
C4 N1 1.376(4) . ?
C4 S1 1.732(4) . ?
C5 C6 1.335(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.459(5) . ?
C6 H6 0.9300 . ?
C7 C12 1.378(6) . ?
C7 C8 1.379(6) . ?
C8 C9 1.394(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.368(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.360(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(6) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 N3 1.126(6) . ?
C14 N2 1.382(4) . ?
C14 C19 1.387(5) . ?
C14 C15 1.391(5) . ?
C15 C16 1.358(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.410(5) . ?
C16 H16 0.9300 . ?
C17 N4 1.358(5) . ?
C17 C18 1.409(5) . ?
C18 C19 1.371(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.443(7) . ?
C20 N4 1.566(6) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 N4 1.472(5) . ?
C22 C23 1.501(7) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
N1 N2 1.285(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
C2 C1 C5 127.3(3) . . ?
C2 C1 S1 110.3(3) . . ?
C5 C1 S1 122.3(3) . . ?
C1 C2 C3 114.4(3) . . ?
C1 C2 Cl1 123.7(3) . . ?
C3 C2 Cl1 121.8(3) . . ?
C4 C3 C2 112.0(3) . . ?
C4 C3 C13 123.1(3) . . ?
C2 C3 C13 124.8(3) . . ?
C3 C4 N1 123.8(3) . . ?
C3 C4 S1 111.5(3) . . ?
N1 C4 S1 124.6(3) . . ?
C6 C5 C1 126.9(4) . . ?
C6 C5 H5 116.5 . . ?
C1 C5 H5 116.5 . . ?
C5 C6 C7 125.8(4) . . ?
C5 C6 H6 117.1 . . ?
C7 C6 H6 117.1 . . ?
C12 C7 C8 117.8(4) . . ?
C12 C7 C6 123.0(4) . . ?
C8 C7 C6 119.2(4) . . ?
C7 C8 C9 121.2(5) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C10 C9 C8 119.2(5) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C11 C10 C9 120.4(5) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 120.2(5) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C7 C12 C11 121.2(5) . . ?
C7 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
N3 C13 C3 179.4(6) . . ?
N2 C14 C19 116.7(3) . . ?
N2 C14 C15 125.4(3) . . ?
C19 C14 C15 117.9(3) . . ?
C16 C15 C14 121.0(3) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 121.9(4) . . ?
C15 C16 H16 119.0 . . ?
C17 C16 H16 119.0 . . ?
N4 C17 C18 121.4(3) . . ?
N4 C17 C16 121.9(4) . . ?
C18 C17 C16 116.7(3) . . ?
C19 C18 C17 120.6(3) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C14 121.8(3) . . ?
C18 C19 H19 119.1 . . ?
C14 C19 H19 119.1 . . ?
C21 C20 N4 100.4(5) . . ?
C21 C20 H20A 111.7 . . ?
N4 C20 H20A 111.7 . . ?
C21 C20 H20B 111.7 . . ?
N4 C20 H20B 111.7 . . ?
H20A C20 H20B 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N4 C22 C23 112.0(4) . . ?
N4 C22 H22A 109.2 . . ?
C23 C22 H22A 109.2 . . ?
N4 C22 H22B 109.2 . . ?
C23 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N2 N1 C4 113.0(3) . . ?
N1 N2 C14 115.5(3) . . ?
C17 N4 C22 121.9(4) . . ?
C17 N4 C20 120.2(4) . . ?
C22 N4 C20 117.0(4) . . ?
C4 S1 C1 91.70(17) . . ?

_refine_diff_density_max         1.158
_refine_diff_density_min         -0.683
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_trans-7
_database_code_depnum_ccdc_archive 'CCDC 1892461'
loop_
_audit_author_name
_audit_author_address
'Wei Huang' 'Nanjing University'
_audit_update_record             
;
2019-01-22 deposited with the CCDC.	2019-12-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H23 Cl N4 S'
_chemical_formula_sum            'C24 H23 Cl N4 S'
_chemical_formula_weight         434.97

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'
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      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                   7.9024(15)
_cell_length_b                   9.4958(17)
_cell_length_c                   15.018(3)
_cell_angle_alpha                78.986(4)
_cell_angle_beta                 87.800(5)
_cell_angle_gamma                85.372(5)
_cell_volume                     1102.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    2695
_cell_measurement_theta_min      2.360
_cell_measurement_theta_max      26.904

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.286
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_process_details   'SADABS, Bruker(2000)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'BRUKER Smart Apex CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8761
_diffrn_reflns_av_unetI/netI     0.0933
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.360
_diffrn_reflns_theta_max         27.549
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             5033
_reflns_number_gt                3277
_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       'SMART (BRUKER 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (BRUKER 2000)'
_computing_structure_solution    'SHELXTL (BRUKER 2000)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0453P)²+0.2756P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5033
_refine_ls_number_parameters     294
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0525
_refine_ls_wR_factor_ref         0.1248
_refine_ls_wR_factor_gt          0.1076
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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 1.4339(3) 0.0834(3) 0.86169(16) 0.0244(5) Uani 1 1 d . . . . .
C2 C 1.4506(3) -0.0228(2) 0.81132(16) 0.0246(5) Uani 1 1 d . . . . .
C3 C 1.3036(3) -0.0354(3) 0.76249(15) 0.0252(6) Uani 1 1 d . . . . .
C4 C 1.1742(3) 0.0641(3) 0.77594(15) 0.0244(5) Uani 1 1 d . . . . .
C5 C 1.5637(3) 0.1254(3) 0.91452(16) 0.0266(6) Uani 1 1 d . . . . .
H5 H 1.6700 0.0758 0.9137 0.032 Uiso 1 1 calc R U . . .
C6 C 1.5466(3) 0.2284(3) 0.96451(15) 0.0271(6) Uani 1 1 d . . . . .
H6 H 1.4389 0.2744 0.9684 0.033 Uiso 1 1 calc R U . . .
C7 C 1.6818(3) 0.2754(3) 1.01374(15) 0.0252(6) Uani 1 1 d . . . . .
C8 C 1.6411(3) 0.3759(3) 1.07005(16) 0.0266(6) Uani 1 1 d . . . . .
H8 H 1.5284 0.4092 1.0771 0.032 Uiso 1 1 calc R U . . .
C9 C 1.7661(3) 0.4264(3) 1.11540(16) 0.0286(6) Uani 1 1 d . . . . .
H9 H 1.7359 0.4935 1.1521 0.034 Uiso 1 1 calc R U . . .
C10 C 1.9355(3) 0.3786(3) 1.10693(16) 0.0271(6) Uani 1 1 d . . . . .
C11 C 1.9758(3) 0.2758(3) 1.05213(17) 0.0325(6) Uani 1 1 d . . . . .
H11 H 2.0882 0.2408 1.0463 0.039 Uiso 1 1 calc R U . . .
C12 C 1.8518(3) 0.2258(3) 1.00678(17) 0.0317(6) Uani 1 1 d . . . . .
H12 H 1.8822 0.1578 0.9709 0.038 Uiso 1 1 calc R U . . .
C13 C 2.0734(3) 0.4356(3) 1.15443(18) 0.0374(7) Uani 1 1 d . . . . .
H13A H 2.0355 0.5290 1.1663 0.056 Uiso 1 1 calc R U . . .
H13B H 2.1740 0.4426 1.1165 0.056 Uiso 1 1 calc R U . . .
H13C H 2.0980 0.3712 1.2107 0.056 Uiso 1 1 calc R U . . .
C14 C 1.2941(3) -0.1361(3) 0.70284(17) 0.0318(6) Uani 1 1 d . . . . .
C15 C 0.7755(3) 0.2196(3) 0.70192(15) 0.0234(5) Uani 1 1 d . . . . .
C16 C 0.7270(3) 0.1421(3) 0.63675(16) 0.0285(6) Uani 1 1 d . . . . .
H16 H 0.7942 0.0616 0.6263 0.034 Uiso 1 1 calc R U . . .
C17 C 0.5820(3) 0.1846(3) 0.58895(17) 0.0327(6) Uani 1 1 d . . . . .
H17 H 0.5498 0.1299 0.5482 0.039 Uiso 1 1 calc R U . . .
C18 C 0.4792(3) 0.3102(3) 0.59992(17) 0.0306(6) Uani 1 1 d . . . . .
C19 C 0.5270(3) 0.3852(3) 0.66742(16) 0.0266(6) Uani 1 1 d . . . . .
H19 H 0.4604 0.4657 0.6785 0.032 Uiso 1 1 calc R U . . .
C20 C 0.6715(3) 0.3391(3) 0.71635(16) 0.0264(6) Uani 1 1 d . . . . .
H20 H 0.7005 0.3892 0.7603 0.032 Uiso 1 1 calc R U . . .
C21 C 0.3037(5) 0.2943(5) 0.4682(3) 0.0298(13) Uani 0.703(10) 1 d . . P A 1
H21A H 0.4070 0.2525 0.4436 0.036 Uiso 0.703(10) 1 calc R U P A 1
H21B H 0.2519 0.3668 0.4206 0.036 Uiso 0.703(10) 1 calc R U P A 1
C22 C 0.1822(7) 0.1784(6) 0.5015(3) 0.0514(16) Uani 0.703(10) 1 d . . P A 1
H22A H 0.2373 0.1036 0.5453 0.077 Uiso 0.703(10) 1 calc R U P A 1
H22B H 0.1490 0.1388 0.4511 0.077 Uiso 0.703(10) 1 calc R U P A 1
H22C H 0.0833 0.2195 0.5290 0.077 Uiso 0.703(10) 1 calc R U P A 1
C21' C 0.2350(13) 0.2402(13) 0.5192(8) 0.033(3) Uani 0.297(10) 1 d . . P A 2
H21C H 0.2681 0.1453 0.5533 0.039 Uiso 0.297(10) 1 calc R U P A 2
H21D H 0.1141 0.2617 0.5280 0.039 Uiso 0.297(10) 1 calc R U P A 2
C22' C 0.2829(14) 0.2531(12) 0.4206(8) 0.045(4) Uani 0.297(10) 1 d . . P A 2
H22D H 0.2689 0.3521 0.3911 0.068 Uiso 0.297(10) 1 calc R U P A 2
H22E H 0.2113 0.1974 0.3930 0.068 Uiso 0.297(10) 1 calc R U P A 2
H22F H 0.3993 0.2178 0.4146 0.068 Uiso 0.297(10) 1 calc R U P A 2
C23 C 0.2465(3) 0.4962(3) 0.55347(17) 0.0334(6) Uani 1 1 d . . . . .
H23A H 0.1924 0.5345 0.4961 0.040 Uiso 1 1 calc R U . . .
H23B H 0.3241 0.5650 0.5640 0.040 Uiso 1 1 calc R U . . .
C24 C 0.1119(3) 0.4816(3) 0.62822(19) 0.0418(7) Uani 1 1 d . . . . .
H24A H 0.0293 0.4195 0.6159 0.063 Uiso 1 1 calc R U . . .
H24B H 0.0572 0.5747 0.6311 0.063 Uiso 1 1 calc R U . . .
H24C H 0.1637 0.4414 0.6852 0.063 Uiso 1 1 calc R U . . .
Cl1 Cl 1.63362(8) -0.13331(7) 0.80562(4) 0.03240(18) Uani 1 1 d . . . . .
N1 N 1.2909(3) -0.2152(3) 0.65456(16) 0.0469(7) Uani 1 1 d . . . . .
N2 N 1.0217(3) 0.0820(2) 0.73205(13) 0.0263(5) Uani 1 1 d . . . . .
N3 N 0.9240(3) 0.1884(2) 0.75102(13) 0.0260(5) Uani 1 1 d . . . . .
N4 N 0.3440(3) 0.3611(3) 0.54628(16) 0.0469(7) Uani 1 1 d . . . . .
S1 S 1.23181(8) 0.17235(7) 0.84990(4) 0.02632(17) 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 C2 1.367(3) . ?
C1 C5 1.446(3) . ?
C1 S1 1.744(2) . ?
C2 C3 1.423(3) . ?
C2 Cl1 1.726(3) . ?
C3 C4 1.371(3) . ?
C3 C14 1.437(3) . ?
C4 N2 1.379(3) . ?
C4 S1 1.746(2) . ?
C5 C6 1.338(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.467(3) . ?
C6 H6 0.9300 . ?
C7 C12 1.394(4) . ?
C7 C8 1.403(3) . ?
C8 C9 1.387(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.387(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.402(3) . ?
C10 C13 1.514(3) . ?
C11 C12 1.378(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 N1 1.142(3) . ?
C15 N3 1.391(3) . ?
C15 C20 1.393(3) . ?
C15 C16 1.412(3) . ?
C16 C17 1.367(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.420(4) . ?
C17 H17 0.9300 . ?
C18 N4 1.363(3) . ?
C18 C19 1.424(3) . ?
C19 C20 1.377(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 N4 1.491(5) . ?
C21 C22 1.519(8) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C21' C22' 1.498(18) . ?
C21' N4 1.609(13) . ?
C21' H21C 0.9700 . ?
C21' H21D 0.9700 . ?
C22' H22D 0.9600 . ?
C22' H22E 0.9600 . ?
C22' H22F 0.9600 . ?
C23 N4 1.462(3) . ?
C23 C24 1.511(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
N2 N3 1.290(3) . ?

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 C5 126.7(2) . . ?
C2 C1 S1 110.44(17) . . ?
C5 C1 S1 122.76(19) . . ?
C1 C2 C3 114.4(2) . . ?
C1 C2 Cl1 123.75(18) . . ?
C3 C2 Cl1 121.83(19) . . ?
C4 C3 C2 112.0(2) . . ?
C4 C3 C14 123.9(2) . . ?
C2 C3 C14 124.1(2) . . ?
C3 C4 N2 124.0(2) . . ?
C3 C4 S1 111.59(17) . . ?
N2 C4 S1 124.28(19) . . ?
C6 C5 C1 126.6(2) . . ?
C6 C5 H5 116.7 . . ?
C1 C5 H5 116.7 . . ?
C5 C6 C7 126.1(2) . . ?
C5 C6 H6 117.0 . . ?
C7 C6 H6 117.0 . . ?
C12 C7 C8 117.5(2) . . ?
C12 C7 C6 123.0(2) . . ?
C8 C7 C6 119.4(2) . . ?
C9 C8 C7 121.1(2) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 121.0(2) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C9 C10 C11 117.8(2) . . ?
C9 C10 C13 121.5(2) . . ?
C11 C10 C13 120.7(2) . . ?
C12 C11 C10 121.2(2) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C7 121.2(2) . . ?
C11 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 C3 178.2(3) . . ?
N3 C15 C20 117.0(2) . . ?
N3 C15 C16 124.7(2) . . ?
C20 C15 C16 118.3(2) . . ?
C17 C16 C15 120.5(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 121.7(2) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 H17 119.1 . . ?
N4 C18 C17 122.0(2) . . ?
N4 C18 C19 120.7(2) . . ?
C17 C18 C19 117.2(2) . . ?
C20 C19 C18 120.2(2) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C15 122.0(2) . . ?
C19 C20 H20 119.0 . . ?
C15 C20 H20 119.0 . . ?
N4 C21 C22 108.5(4) . . ?
N4 C21 H21A 110.0 . . ?
C22 C21 H21A 110.0 . . ?
N4 C21 H21B 110.0 . . ?
C22 C21 H21B 110.0 . . ?
H21A C21 H21B 108.4 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C22' C21' N4 100.8(9) . . ?
C22' C21' H21C 111.6 . . ?
N4 C21' H21C 111.6 . . ?
C22' C21' H21D 111.6 . . ?
N4 C21' H21D 111.6 . . ?
H21C C21' H21D 109.4 . . ?
C21' C22' H22D 109.5 . . ?
C21' C22' H22E 109.5 . . ?
H22D C22' H22E 109.5 . . ?
C21' C22' H22F 109.5 . . ?
H22D C22' H22F 109.5 . . ?
H22E C22' H22F 109.5 . . ?
N4 C23 C24 113.9(2) . . ?
N4 C23 H23A 108.8 . . ?
C24 C23 H23A 108.8 . . ?
N4 C23 H23B 108.8 . . ?
C24 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N3 N2 C4 112.97(19) . . ?
N2 N3 C15 115.18(19) . . ?
C18 N4 C23 121.7(2) . . ?
C18 N4 C21 121.7(3) . . ?
C23 N4 C21 116.0(2) . . ?
C18 N4 C21' 115.4(4) . . ?
C23 N4 C21' 114.8(4) . . ?
C1 S1 C4 91.57(12) . . ?

_refine_diff_density_max         0.340
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_cis-6
_database_code_depnum_ccdc_archive 'CCDC 1892459'
loop_
_audit_author_name
_audit_author_address
'Wei Huang' 'Nanjing University'
_audit_update_record             
;
2019-01-22 deposited with the CCDC.	2019-12-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H21 Cl N4 S'
_chemical_formula_sum            'C23 H21 Cl N4 S'
_chemical_formula_weight         420.95

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'
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      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                   12.225(4)
_cell_length_b                   12.945(4)
_cell_length_c                   15.227(5)
_cell_angle_alpha                114.539(5)
_cell_angle_beta                 95.090(6)
_cell_angle_gamma                93.604(5)
_cell_volume                     2170.2(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    1580
_cell_measurement_theta_min      2.379
_cell_measurement_theta_max      19.578

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.289
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_process_details   'SADABS, Bruker(2000)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'BRUKER Smart Apex CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16377
_diffrn_reflns_av_unetI/netI     0.1508
_diffrn_reflns_av_R_equivalents  0.0908
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.683
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             7575
_reflns_number_gt                3411
_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       'SMART (BRUKER 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (BRUKER 2000)'
_computing_structure_solution    'SHELXTL (BRUKER 2000)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0385P)²+0.7900P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7575
_refine_ls_number_parameters     546
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.1627
_refine_ls_R_factor_gt           0.0805
_refine_ls_wR_factor_ref         0.2216
_refine_ls_wR_factor_gt          0.1853
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_restrained_S_all      0.965
_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 -0.0008(4) 0.1689(5) 0.6244(3) 0.0645(14) Uani 1 1 d . . . . .
C2 C -0.0150(4) 0.0700(4) 0.6363(3) 0.0617(13) Uani 1 1 d . . . . .
C3 C 0.0720(4) 0.0516(4) 0.6922(3) 0.0605(13) Uani 1 1 d . . . . .
C4 C 0.1542(4) 0.1402(4) 0.7274(3) 0.0575(12) Uani 1 1 d . . . . .
C5 C -0.0835(5) 0.2110(6) 0.5805(4) 0.097(2) Uani 1 1 d . . . . .
H5 H -0.1513 0.1661 0.5608 0.116 Uiso 1 1 calc R U . . .
C6 C -0.0813(6) 0.3017(7) 0.5628(5) 0.114(2) Uani 1 1 d . . . . .
H6 H -0.1487 0.3134 0.5369 0.137 Uiso 1 1 calc R U . . .
C7 C 0.0073(6) 0.3844(5) 0.5767(4) 0.0867(19) Uani 1 1 d . . . . .
C8 C 0.1057(7) 0.3528(6) 0.5342(5) 0.107(2) Uani 1 1 d . . . . .
H8 H 0.1126 0.2754 0.5012 0.128 Uiso 1 1 calc R U . . .
C9 C 0.1940(6) 0.4320(7) 0.5389(6) 0.112(2) Uani 1 1 d . . . . .
H9 H 0.2557 0.4068 0.5079 0.135 Uiso 1 1 calc R U . . .
C10 C 0.1870(9) 0.5449(8) 0.5894(7) 0.141(4) Uani 1 1 d . . . . .
H10 H 0.2453 0.5985 0.5964 0.170 Uiso 1 1 calc R U . . .
C11 C 0.0877(10) 0.5809(7) 0.6324(6) 0.132(4) Uani 1 1 d . . . . .
H11 H 0.0811 0.6582 0.6667 0.159 Uiso 1 1 calc R U . . .
C12 C 0.0018(7) 0.4998(7) 0.6223(5) 0.110(2) Uani 1 1 d . . . . .
H12 H -0.0629 0.5251 0.6479 0.132 Uiso 1 1 calc R U . . .
C13 C 0.0748(5) -0.0458(5) 0.7117(4) 0.0725(15) Uani 1 1 d . . . . .
C14 C 0.4055(4) 0.2444(4) 0.8788(3) 0.0572(12) Uani 1 1 d . . . . .
C15 C 0.4875(4) 0.3338(4) 0.9026(3) 0.0644(14) Uani 1 1 d . . . . .
H15 H 0.4812 0.3835 0.8730 0.077 Uiso 1 1 calc R U . . .
C16 C 0.5775(4) 0.3504(4) 0.9686(4) 0.0683(15) Uani 1 1 d . . . . .
H16 H 0.6309 0.4115 0.9833 0.082 Uiso 1 1 calc R U . . .
C17 C 0.5916(4) 0.2773(4) 1.0149(3) 0.0619(13) Uani 1 1 d . . . . .
C18 C 0.5068(4) 0.1873(4) 0.9899(3) 0.0637(14) Uani 1 1 d . . . . .
H18 H 0.5119 0.1376 1.0197 0.076 Uiso 1 1 calc R U . . .
C19 C 0.4183(4) 0.1712(4) 0.9238(3) 0.0641(14) Uani 1 1 d . . . . .
H19 H 0.3649 0.1098 0.9082 0.077 Uiso 1 1 calc R U . . .
C20 C 0.6914(5) 0.2217(5) 1.1346(4) 0.092(2) Uani 1 1 d . . . . .
H20A H 0.7402 0.2640 1.1948 0.111 Uiso 1 1 calc R U . . .
H20B H 0.6194 0.2067 1.1516 0.111 Uiso 1 1 calc R U . . .
C21 C 0.7338(6) 0.1122(6) 1.0807(5) 0.124(3) Uani 1 1 d . . . . .
H21A H 0.6903 0.0727 1.0182 0.186 Uiso 1 1 calc R U . . .
H21B H 0.7296 0.0664 1.1165 0.186 Uiso 1 1 calc R U . . .
H21C H 0.8094 0.1258 1.0721 0.186 Uiso 1 1 calc R U . . .
C22 C 0.7849(8) 0.3586(10) 1.0797(9) 0.066(4) Uani 0.65(2) 1 d . . P . .
H22A H 0.8480 0.3224 1.0921 0.079 Uiso 0.65(2) 1 calc R U P . .
H22B H 0.7861 0.3585 1.0161 0.079 Uiso 0.65(2) 1 calc R U P . .
C23 C 0.7924(10) 0.4769(10) 1.1546(8) 0.080(5) Uani 0.65(2) 1 d . . P . .
H23A H 0.7394 0.5173 1.1349 0.119 Uiso 0.65(2) 1 calc R U P . .
H23B H 0.8654 0.5141 1.1624 0.119 Uiso 0.65(2) 1 calc R U P . .
H23C H 0.7773 0.4765 1.2153 0.119 Uiso 0.65(2) 1 calc R U P . .
C24 C 0.5239(4) 0.8998(4) 0.3772(3) 0.0536(12) Uani 1 1 d . . . . .
C25 C 0.5397(4) 0.9850(4) 0.3476(3) 0.0565(12) Uani 1 1 d . . . . .
C26 C 0.4504(4) 0.9892(4) 0.2848(3) 0.0557(12) Uani 1 1 d . . . . .
C27 C 0.3667(4) 0.9043(4) 0.2647(3) 0.0522(12) Uani 1 1 d . . . . .
C28 C 0.5977(4) 0.8836(4) 0.4497(4) 0.0677(14) Uani 1 1 d . . . . .
H28 H 0.6502 0.9453 0.4868 0.081 Uiso 1 1 calc R U . . .
C29 C 0.6018(5) 0.7946(4) 0.4712(4) 0.0781(16) Uani 1 1 d . . . . .
H29 H 0.6474 0.8061 0.5274 0.094 Uiso 1 1 calc R U . . .
C30 C 0.5426(4) 0.6798(4) 0.4163(4) 0.0675(14) Uani 1 1 d D . . . .
C31 C 0.4694(7) 0.6341(6) 0.4574(6) 0.147(3) Uani 1 1 d D U . . .
H31 H 0.4528 0.6796 0.5193 0.176 Uiso 1 1 calc R U . . .
C32 C 0.4199(8) 0.5239(6) 0.4105(6) 0.160(3) Uani 1 1 d D U . . .
H32 H 0.3681 0.4971 0.4394 0.192 Uiso 1 1 calc R U . . .
C33 C 0.4464(7) 0.4537(6) 0.3218(5) 0.121(3) Uani 1 1 d D U . . .
H33 H 0.4172 0.3774 0.2911 0.146 Uiso 1 1 calc R U . . .
C34 C 0.5173(5) 0.4991(5) 0.2793(5) 0.101(2) Uani 1 1 d D . . . .
H34 H 0.5333 0.4536 0.2172 0.121 Uiso 1 1 calc R U . . .
C35 C 0.5660(5) 0.6104(5) 0.3257(4) 0.0849(17) Uani 1 1 d D . . . .
H35 H 0.6149 0.6383 0.2952 0.102 Uiso 1 1 calc R U . . .
C36 C 0.4464(5) 1.0724(5) 0.2455(4) 0.0763(16) Uani 1 1 d . . . . .
C37 C 0.1035(4) 0.7944(4) 0.1353(3) 0.0509(11) Uani 1 1 d . . . . .
C38 C 0.0731(4) 0.8697(4) 0.0965(3) 0.0624(14) Uani 1 1 d . . . . .
H38 H 0.1179 0.9376 0.1134 0.075 Uiso 1 1 calc R U . . .
C39 C -0.0225(4) 0.8452(4) 0.0333(3) 0.0674(15) Uani 1 1 d . . . . .
H39 H -0.0399 0.8957 0.0064 0.081 Uiso 1 1 calc R U . . .
C40 C -0.0947(4) 0.7450(4) 0.0083(3) 0.0596(13) Uani 1 1 d . . . . .
C41 C -0.0617(4) 0.6713(4) 0.0502(3) 0.0619(13) Uani 1 1 d . . . . .
H41 H -0.1058 0.6033 0.0345 0.074 Uiso 1 1 calc R U . . .
C42 C 0.0319(4) 0.6966(4) 0.1123(3) 0.0584(13) Uani 1 1 d . . . . .
H42 H 0.0490 0.6473 0.1405 0.070 Uiso 1 1 calc R U . . .
C43 C -0.2605(5) 0.6136(4) -0.0842(4) 0.0812(17) Uani 1 1 d . . . . .
H43A H -0.3344 0.6233 -0.1063 0.097 Uiso 1 1 calc R U . . .
H43B H -0.2650 0.5970 -0.0280 0.097 Uiso 1 1 calc R U . . .
C44 C -0.2214(6) 0.5136(5) -0.1632(5) 0.113(2) Uani 1 1 d . . . . .
H44A H -0.2249 0.5252 -0.2217 0.170 Uiso 1 1 calc R U . . .
H44B H -0.2677 0.4453 -0.1750 0.170 Uiso 1 1 calc R U . . .
H44C H -0.1466 0.5062 -0.1437 0.170 Uiso 1 1 calc R U . . .
C45 C -0.2199(5) 0.7957(4) -0.0996(4) 0.0778(16) Uani 1 1 d . . . . .
H45A H -0.2015 0.8743 -0.0520 0.093 Uiso 1 1 calc R U . . .
H45B H -0.2993 0.7833 -0.1180 0.093 Uiso 1 1 calc R U . . .
C46 C -0.1642(6) 0.7790(5) -0.1884(5) 0.108(2) Uani 1 1 d . . . . .
H46A H -0.0857 0.7953 -0.1705 0.162 Uiso 1 1 calc R U . . .
H46B H -0.1900 0.8297 -0.2152 0.162 Uiso 1 1 calc R U . . .
H46C H -0.1817 0.7014 -0.2361 0.162 Uiso 1 1 calc R U . . .
C22' C 0.7445(17) 0.4170(11) 1.1437(15) 0.076(7) Uani 0.35(2) 1 d D . P . .
H22C H 0.7065 0.4743 1.1317 0.091 Uiso 0.35(2) 1 calc R U P . .
H22D H 0.7501 0.4353 1.2126 0.091 Uiso 0.35(2) 1 calc R U P . .
Cl1 Cl -0.13307(12) -0.02679(13) 0.58643(10) 0.0902(5) Uani 1 1 d . . . . .
Cl2 Cl 0.65511(12) 1.08357(11) 0.38738(11) 0.0833(5) Uani 1 1 d . . . . .
N1 N 0.2460(3) 0.1462(3) 0.7884(3) 0.0577(10) Uani 1 1 d . . . . .
N2 N 0.3154(3) 0.2350(3) 0.8124(3) 0.0580(10) Uani 1 1 d . . . . .
N3 N 0.0739(5) -0.1235(4) 0.7299(4) 0.1073(19) Uani 1 1 d . . . . .
N4 N 0.6811(4) 0.2935(4) 1.0812(3) 0.0833(15) Uani 1 1 d D . . . .
N5 N 0.2705(3) 0.8934(3) 0.2052(3) 0.0586(10) Uani 1 1 d . . . . .
N6 N 0.2018(3) 0.8079(3) 0.1941(3) 0.0552(10) Uani 1 1 d . . . . .
N7 N 0.4450(5) 1.1398(4) 0.2150(4) 0.112(2) Uani 1 1 d . . . . .
N8 N -0.1897(3) 0.7209(3) -0.0542(3) 0.0693(12) Uani 1 1 d . . . . .
S1 S 0.12597(11) 0.24373(11) 0.68650(9) 0.0671(4) Uani 1 1 d . . . . .
S2 S 0.39729(11) 0.81925(10) 0.32336(9) 0.0587(4) Uani 1 1 d . . . . .
C23' C 0.852(2) 0.4116(18) 1.1119(18) 0.149(12) Uani 0.35(2) 1 d . . P . .
H23D H 0.8956 0.4843 1.1471 0.223 Uiso 0.35(2) 1 calc R U P . .
H23E H 0.8883 0.3540 1.1238 0.223 Uiso 0.35(2) 1 calc R U P . .
H23F H 0.8450 0.3928 1.0435 0.223 Uiso 0.35(2) 1 calc R U P . .


_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 1.369(7) . ?
C1 C5 1.421(7) . ?
C1 S1 1.739(5) . ?
C2 C3 1.396(6) . ?
C2 Cl1 1.737(5) . ?
C3 C4 1.365(6) . ?
C3 C13 1.412(7) . ?
C4 N1 1.368(5) . ?
C4 S1 1.737(5) . ?
C5 C6 1.308(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.411(9) . ?
C6 H6 0.9300 . ?
C7 C12 1.370(8) . ?
C7 C8 1.419(9) . ?
C8 C9 1.417(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.353(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.441(12) . ?
C10 H10 0.9300 . ?
C11 C12 1.389(11) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 N3 1.148(6) . ?
C14 C15 1.385(6) . ?
C14 C19 1.390(6) . ?
C14 N2 1.391(6) . ?
C15 C16 1.364(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.406(6) . ?
C16 H16 0.9300 . ?
C17 N4 1.363(6) . ?
C17 C18 1.409(6) . ?
C18 C19 1.353(6) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.468(8) . ?
C20 N4 1.471(6) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.47(2) . ?
C22 N4 1.487(11) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.363(6) . ?
C24 C28 1.455(6) . ?
C24 S2 1.738(5) . ?
C25 C26 1.406(6) . ?
C25 Cl2 1.722(4) . ?
C26 C27 1.368(6) . ?
C26 C36 1.435(7) . ?
C27 N5 1.381(5) . ?
C27 S2 1.720(4) . ?
C28 C29 1.325(7) . ?
C28 H28 0.9300 . ?
C29 C30 1.468(6) . ?
C29 H29 0.9300 . ?
C30 C35 1.365(6) . ?
C30 C31 1.371(7) . ?
C31 C32 1.371(7) . ?
C31 H31 0.9300 . ?
C32 C33 1.360(7) . ?
C32 H32 0.9300 . ?
C33 C34 1.367(7) . ?
C33 H33 0.9300 . ?
C34 C35 1.378(6) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C36 N7 1.146(6) . ?
C37 C38 1.386(6) . ?
C37 C42 1.389(6) . ?
C37 N6 1.390(5) . ?
C38 C39 1.377(6) . ?
C38 H38 0.9300 . ?
C39 C40 1.411(6) . ?
C39 H39 0.9300 . ?
C40 N8 1.366(6) . ?
C40 C41 1.410(6) . ?
C41 C42 1.347(6) . ?
C41 H41 0.9300 . ?
C42 H42 0.9300 . ?
C43 N8 1.463(6) . ?
C43 C44 1.496(8) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C45 N8 1.451(6) . ?
C45 C46 1.510(8) . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
C22' C23' 1.44(4) . ?
C22' N4 1.585(10) . ?
C22' H22C 0.9700 . ?
C22' H22D 0.9700 . ?
N1 N2 1.283(5) . ?
N5 N6 1.290(5) . ?
C23' H23D 0.9600 . ?
C23' H23E 0.9600 . ?
C23' H23F 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 C5 124.8(5) . . ?
C2 C1 S1 109.2(4) . . ?
C5 C1 S1 125.4(4) . . ?
C1 C2 C3 115.6(4) . . ?
C1 C2 Cl1 122.8(4) . . ?
C3 C2 Cl1 121.6(4) . . ?
C4 C3 C2 111.9(4) . . ?
C4 C3 C13 123.5(5) . . ?
C2 C3 C13 124.6(5) . . ?
C3 C4 N1 123.7(4) . . ?
C3 C4 S1 111.4(4) . . ?
N1 C4 S1 124.9(4) . . ?
C6 C5 C1 131.5(6) . . ?
C6 C5 H5 114.3 . . ?
C1 C5 H5 114.3 . . ?
C5 C6 C7 130.1(7) . . ?
C5 C6 H6 114.9 . . ?
C7 C6 H6 114.9 . . ?
C12 C7 C6 123.6(8) . . ?
C12 C7 C8 114.8(7) . . ?
C6 C7 C8 121.2(6) . . ?
C9 C8 C7 124.0(7) . . ?
C9 C8 H8 118.0 . . ?
C7 C8 H8 118.0 . . ?
C10 C9 C8 118.8(8) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C9 C10 C11 119.0(9) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C12 C11 C10 119.8(8) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C7 C12 C11 123.4(8) . . ?
C7 C12 H12 118.3 . . ?
C11 C12 H12 118.3 . . ?
N3 C13 C3 177.3(7) . . ?
C15 C14 C19 117.7(4) . . ?
C15 C14 N2 117.7(4) . . ?
C19 C14 N2 124.6(4) . . ?
C16 C15 C14 121.3(4) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C17 121.7(4) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
N4 C17 C16 122.0(4) . . ?
N4 C17 C18 121.9(4) . . ?
C16 C17 C18 116.0(4) . . ?
C19 C18 C17 121.8(4) . . ?
C19 C18 H18 119.1 . . ?
C17 C18 H18 119.1 . . ?
C18 C19 C14 121.5(4) . . ?
C18 C19 H19 119.3 . . ?
C14 C19 H19 119.3 . . ?
C21 C20 N4 114.4(6) . . ?
C21 C20 H20A 108.7 . . ?
N4 C20 H20A 108.7 . . ?
C21 C20 H20B 108.7 . . ?
N4 C20 H20B 108.7 . . ?
H20A C20 H20B 107.6 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 N4 109.8(9) . . ?
C23 C22 H22A 109.7 . . ?
N4 C22 H22A 109.7 . . ?
C23 C22 H22B 109.7 . . ?
N4 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C28 125.2(4) . . ?
C25 C24 S2 110.4(3) . . ?
C28 C24 S2 124.2(4) . . ?
C24 C25 C26 113.9(4) . . ?
C24 C25 Cl2 123.7(4) . . ?
C26 C25 Cl2 122.4(4) . . ?
C27 C26 C25 112.4(4) . . ?
C27 C26 C36 123.3(4) . . ?
C25 C26 C36 124.4(4) . . ?
C26 C27 N5 121.9(4) . . ?
C26 C27 S2 111.7(3) . . ?
N5 C27 S2 126.4(4) . . ?
C29 C28 C24 130.0(5) . . ?
C29 C28 H28 115.0 . . ?
C24 C28 H28 115.0 . . ?
C28 C29 C30 127.4(5) . . ?
C28 C29 H29 116.3 . . ?
C30 C29 H29 116.3 . . ?
C35 C30 C31 117.2(5) . . ?
C35 C30 C29 121.1(5) . . ?
C31 C30 C29 121.3(5) . . ?
C32 C31 C30 122.4(7) . . ?
C32 C31 H31 118.8 . . ?
C30 C31 H31 118.8 . . ?
C33 C32 C31 120.2(7) . . ?
C33 C32 H32 119.9 . . ?
C31 C32 H32 119.9 . . ?
C32 C33 C34 117.8(7) . . ?
C32 C33 H33 121.1 . . ?
C34 C33 H33 121.1 . . ?
C33 C34 C35 122.0(6) . . ?
C33 C34 H34 119.0 . . ?
C35 C34 H34 119.0 . . ?
C30 C35 C34 120.3(6) . . ?
C30 C35 H35 119.9 . . ?
C34 C35 H35 119.9 . . ?
N7 C36 C26 178.8(6) . . ?
C38 C37 C42 118.0(4) . . ?
C38 C37 N6 124.9(4) . . ?
C42 C37 N6 117.1(4) . . ?
C39 C38 C37 120.8(4) . . ?
C39 C38 H38 119.6 . . ?
C37 C38 H38 119.6 . . ?
C38 C39 C40 121.4(4) . . ?
C38 C39 H39 119.3 . . ?
C40 C39 H39 119.3 . . ?
N8 C40 C41 122.5(4) . . ?
N8 C40 C39 121.4(4) . . ?
C41 C40 C39 116.1(4) . . ?
C42 C41 C40 121.8(4) . . ?
C42 C41 H41 119.1 . . ?
C40 C41 H41 119.1 . . ?
C41 C42 C37 121.8(4) . . ?
C41 C42 H42 119.1 . . ?
C37 C42 H42 119.1 . . ?
N8 C43 C44 114.1(5) . . ?
N8 C43 H43A 108.7 . . ?
C44 C43 H43A 108.7 . . ?
N8 C43 H43B 108.7 . . ?
C44 C43 H43B 108.7 . . ?
H43A C43 H43B 107.6 . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
N8 C45 C46 114.5(5) . . ?
N8 C45 H45A 108.6 . . ?
C46 C45 H45A 108.6 . . ?
N8 C45 H45B 108.6 . . ?
C46 C45 H45B 108.6 . . ?
H45A C45 H45B 107.6 . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C23' C22' N4 105.0(16) . . ?
C23' C22' H22C 110.7 . . ?
N4 C22' H22C 110.7 . . ?
C23' C22' H22D 110.7 . . ?
N4 C22' H22D 110.7 . . ?
H22C C22' H22D 108.8 . . ?
N2 N1 C4 114.7(4) . . ?
N1 N2 C14 114.6(4) . . ?
C17 N4 C20 121.7(4) . . ?
C17 N4 C22 119.7(5) . . ?
C20 N4 C22 116.0(5) . . ?
C17 N4 C22' 120.8(7) . . ?
C20 N4 C22' 110.6(8) . . ?
C22 N4 C22' 43.2(8) . . ?
N6 N5 C27 113.0(4) . . ?
N5 N6 C37 114.8(4) . . ?
C40 N8 C45 121.6(4) . . ?
C40 N8 C43 120.9(4) . . ?
C45 N8 C43 117.3(4) . . ?
C4 S1 C1 91.8(2) . . ?
C27 S2 C24 91.6(2) . . ?
C22' C23' H23D 109.5 . . ?
C22' C23' H23E 109.5 . . ?
H23D C23' H23E 109.5 . . ?
C22' C23' H23F 109.5 . . ?
H23D C23' H23F 109.5 . . ?
H23E C23' H23F 109.5 . . ?

_refine_diff_density_max         0.533
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.071

