# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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. 
# 
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data_293K
_database_code_depnum_ccdc_archive 'CCDC 1437663'
_audit_update_record             
;
2016-02-05 deposited with the CCDC.
2016-02-05 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         'C3 H5 N2, 2(C H4 N2 S), Cl'
_chemical_formula_sum            'C5 H13 Cl N6 S2'
_chemical_formula_weight         256.78

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'
Cl Cl 0.1484 0.1585 '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      orthorhombic
_space_group_IT_number           63
_space_group_name_H-M_alt        'C m c m'
_space_group_name_Hall           '-C 2c 2'

_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+1/2'
'x, -y, -z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, y, -z-1/2'
'-x, y, z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, -z-1/2'
'-x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.750(10)
_cell_length_b                   9.887(10)
_cell_length_c                   8.419(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1227.8(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1802
_cell_measurement_theta_min      3.4633
_cell_measurement_theta_max      27.4778

_exptl_crystal_description       needlelike
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2000
_exptl_crystal_size_mid          0.2000
_exptl_crystal_size_min          0.2000
_exptl_absorpt_coefficient_mu    0.627
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.8902
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_type   Multi-scan

_exptl_absorpt_process_details   
;   Higashi, T.(1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            6359
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.466
_diffrn_reflns_theta_max         27.474
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             774
_reflns_number_gt                731
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0653P)²+3.0478P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         774
_refine_ls_number_parameters     68
_refine_ls_number_restraints     47
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1372
_refine_ls_wR_factor_gt          0.1348
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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 0.6827(2) 0.1758(3) 0.7500 0.0354(7) Uani 1 2 d S T P . .
C2 C 0.5647(18) 0.522(2) 0.523(5) 0.094(9) Uani 0.25 1 d D U P . .
H2A H 0.6286 0.5320 0.5412 0.113 Uiso 0.25 1 d R U P . .
C3 C 0.5219(16) 0.418(3) 0.461(4) 0.085(8) Uani 0.25 1 d D U P . .
H3A H 0.5503 0.3366 0.4240 0.102 Uiso 0.25 1 d R U P . .
C4 C 0.4207(17) 0.562(4) 0.500(4) 0.092(7) Uani 0.25 1 d D U P . .
H4A H 0.3629 0.6048 0.5134 0.111 Uiso 0.25 1 d R U P . .
Cl1 Cl 0.5000 0.90128(12) 0.7500 0.0431(4) Uani 1 4 d S T P . .
N1 N 0.64583(16) 0.1340(2) 0.8840(2) 0.0458(6) Uani 1 1 d . . . . .
H1A H 0.5994 0.0815 0.8820 0.055 Uiso 1 1 calc R U . . .
H1B H 0.6682 0.1594 0.9735 0.055 Uiso 1 1 calc R U . . .
N2 N 0.4349(16) 0.436(4) 0.444(3) 0.081(7) Uani 0.25 1 d D U P . .
H2B H 0.3932 0.3779 0.4054 0.097 Uiso 0.25 1 d R U P . .
N3 N 0.5000 0.616(2) 0.550(3) 0.099(5) Uani 0.5 2 d DS TU P . .
H3B H 0.5095 0.6982 0.5925 0.119 Uiso 0.25 1 d R U P . .
S1 S 0.77488(8) 0.28006(13) 0.7500 0.0608(5) Uani 1 2 d S T 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 N1 1.319(3) 10_557 ?
C1 N1 1.319(3) . ?
C1 S1 1.706(4) . ?
C2 C4 0.49(5) 11_655 ?
C2 N2 0.50(4) 9_666 ?
C2 C2 0.59(5) 3_566 ?
C2 C3 0.88(3) 3_566 ?
C2 C4 0.88(4) 9_666 ?
C2 N2 1.08(5) 11_655 ?
C2 C3 1.32(3) . ?
C2 N3 1.350(10) . ?
C2 C3 1.41(4) 9_666 ?
C2 C3 1.72(4) 11_655 ?
C2 N3 1.77(2) 9_666 ?
C2 C2 1.91(5) 11_655 ?
C2 H2A 0.9600 . ?
C3 N3 0.48(3) 9_666 ?
C3 C3 0.65(5) 11_655 ?
C3 N2 0.67(4) 11_655 ?
C3 C2 0.88(3) 3_566 ?
C3 C4 0.93(2) 9_666 ?
C3 N2 1.302(10) . ?
C3 C2 1.41(4) 9_666 ?
C3 C4 1.54(4) 3_566 ?
C3 C4 1.69(5) 11_655 ?
C3 C2 1.72(4) 11_655 ?
C3 C3 1.75(5) 3_566 ?
C3 H3A 0.9600 . ?
C4 C2 0.49(5) 11_655 ?
C4 N2 0.51(5) 3_566 ?
C4 C2 0.88(4) 9_666 ?
C4 C3 0.93(3) 9_666 ?
C4 C4 1.22(7) 3_566 ?
C4 N2 1.350(10) . ?
C4 N3 1.353(10) . ?
C4 C3 1.54(4) 3_566 ?
C4 C3 1.69(5) 11_655 ?
C4 H4A 0.9599 . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 C2 0.50(4) 9_666 ?
N2 C4 0.51(5) 3_566 ?
N2 C3 0.67(4) 11_655 ?
N2 C2 1.08(5) 11_655 ?
N2 N3 1.09(3) 9_666 ?
N2 N2 1.58(8) 3_566 ?
N2 C3 1.77(4) 9_666 ?
N2 H2B 0.8999 . ?
N3 C3 0.48(3) 9_666 ?
N3 C3 0.48(3) 3_566 ?
N3 N2 1.09(3) 3_566 ?
N3 N2 1.09(3) 9_666 ?
N3 C2 1.350(10) 11_655 ?
N3 C4 1.353(10) 11_655 ?
N3 C2 1.77(2) 9_666 ?
N3 C2 1.77(2) 3_566 ?
N3 H3B 0.9000 . ?

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 N1 117.7(3) 10_557 . ?
N1 C1 S1 121.17(15) 10_557 . ?
N1 C1 S1 121.17(15) . . ?
C4 C2 N2 63(6) 11_655 9_666 ?
C4 C2 C2 109(10) 11_655 3_566 ?
N2 C2 C2 171(10) 9_666 3_566 ?
C4 C2 C3 81(3) 11_655 3_566 ?
N2 C2 C3 50(5) 9_666 3_566 ?
C2 C2 C3 127(6) 3_566 3_566 ?
C4 C2 C4 124(5) 11_655 9_666 ?
N2 C2 C4 155(8) 9_666 9_666 ?
C2 C2 C4 32(5) 3_566 9_666 ?
C3 C2 C4 148(4) 3_566 9_666 ?
C4 C2 N2 113(8) 11_655 11_655 ?
N2 C2 N2 175(7) 9_666 11_655 ?
C2 C2 N2 4(6) 3_566 11_655 ?
C3 C2 N2 129(5) 3_566 11_655 ?
C4 C2 N2 28(3) 9_666 11_655 ?
C4 C2 C3 133(9) 11_655 . ?
N2 C2 C3 152(5) 9_666 . ?
C2 C2 C3 32(3) 3_566 . ?
C3 C2 C3 104(3) 3_566 . ?
C4 C2 C3 44.9(18) 9_666 . ?
N2 C2 C3 31(3) 11_655 . ?
C4 C2 N3 79.9(19) 11_655 . ?
N2 C2 N3 49(4) 9_666 . ?
C2 C2 N3 128(4) 3_566 . ?
C3 C2 N3 1(3) 3_566 . ?
C4 C2 N3 149(3) 9_666 . ?
N2 C2 N3 130(4) 11_655 . ?
C3 C2 N3 105(2) . . ?
C4 C2 C3 96(4) 11_655 9_666 ?
N2 C2 C3 67(4) 9_666 9_666 ?
C2 C2 C3 112(3) 3_566 9_666 ?
C3 C2 C3 18.4(14) 3_566 9_666 ?
C4 C2 C3 130(3) 9_666 9_666 ?
N2 C2 C3 113(4) 11_655 9_666 ?
C3 C2 C3 86(2) . 9_666 ?
N3 C2 C3 19.6(13) . 9_666 ?
C4 C2 C3 133(9) 11_655 11_655 ?
N2 C2 C3 133(6) 9_666 11_655 ?
C2 C2 C3 49.6(19) 3_566 11_655 ?
C3 C2 C3 85(3) 3_566 11_655 ?
C4 C2 C3 63.3(17) 9_666 11_655 ?
N2 C2 C3 49.1(18) 11_655 11_655 ?
C3 C2 C3 19.2(13) . 11_655 ?
N3 C2 C3 86(2) . 11_655 ?
C3 C2 C3 67(2) 9_666 11_655 ?
C4 C2 N3 136(10) 11_655 9_666 ?
N2 C2 N3 147(6) 9_666 9_666 ?
C2 C2 N3 37(3) 3_566 9_666 ?
C3 C2 N3 101(3) 3_566 9_666 ?
C4 C2 N3 47.9(16) 9_666 9_666 ?
N2 C2 N3 35.3(16) 11_655 9_666 ?
C3 C2 N3 4.6(16) . 9_666 ?
N3 C2 N3 102(2) . 9_666 ?
C3 C2 N3 82(2) 9_666 9_666 ?
C3 C2 N3 15.5(8) 11_655 9_666 ?
C4 C2 C2 116(4) 11_655 11_655 ?
N2 C2 C2 91(5) 9_666 11_655 ?
C2 C2 C2 90.003(1) 3_566 11_655 ?
C3 C2 C2 44(2) 3_566 11_655 ?
C4 C2 C2 104(2) 9_666 11_655 ?
N2 C2 C2 90(2) 11_655 11_655 ?
C3 C2 C2 61.3(11) . 11_655 ?
N3 C2 C2 45.0(15) . 11_655 ?
C3 C2 C2 25.4(15) 9_666 11_655 ?
C3 C2 C2 42.1(9) 11_655 11_655 ?
N3 C2 C2 57.5(9) 9_666 11_655 ?
C4 C2 H2A 63.1 11_655 . ?
N2 C2 H2A 79.4 9_666 . ?
C2 C2 H2A 100.5 3_566 . ?
C3 C2 H2A 127.9 3_566 . ?
C4 C2 H2A 83.8 9_666 . ?
N2 C2 H2A 99.9 11_655 . ?
C3 C2 H2A 127.9 . . ?
N3 C2 H2A 126.7 . . ?
C3 C2 H2A 146.0 9_666 . ?
C3 C2 H2A 147.0 11_655 . ?
N3 C2 H2A 131.5 9_666 . ?
C2 C2 H2A 169.2 11_655 . ?
N3 C3 C3 47(4) 9_666 11_655 ?
N3 C3 N2 142(9) 9_666 11_655 ?
C3 C3 N2 161(4) 11_655 11_655 ?
N3 C3 C2 176(7) 9_666 3_566 ?
C3 C3 C2 136(2) 11_655 3_566 ?
N2 C3 C2 35(3) 11_655 3_566 ?
N3 C3 C4 147(7) 9_666 9_666 ?
C3 C3 C4 155(2) 11_655 9_666 ?
N2 C3 C4 33(5) 11_655 9_666 ?
C2 C3 C4 31(3) 3_566 9_666 ?
N3 C3 N2 53(4) 9_666 . ?
C3 C3 N2 9.7(18) 11_655 . ?
N2 C3 N2 151(5) 11_655 . ?
C2 C3 N2 130(4) 3_566 . ?
C4 C3 N2 155(3) 9_666 . ?
N3 C3 C2 163(6) 9_666 . ?
C3 C3 C2 118.7(11) 11_655 . ?
N2 C3 C2 55(5) 11_655 . ?
C2 C3 C2 21(3) 3_566 . ?
C4 C3 C2 42(3) 9_666 . ?
N2 C3 C2 114(3) . . ?
N3 C3 C2 73(4) 9_666 9_666 ?
C3 C3 C2 25.4(15) 11_655 9_666 ?
N2 C3 C2 140(5) 11_655 9_666 ?
C2 C3 C2 111(3) 3_566 9_666 ?
C4 C3 C2 134(3) 9_666 9_666 ?
N2 C3 C2 20.7(18) . 9_666 ?
C2 C3 C2 94(2) . 9_666 ?
N3 C3 C4 58(5) 9_666 3_566 ?
C3 C3 C4 14.5(13) 11_655 3_566 ?
N2 C3 C4 158(4) 11_655 3_566 ?
C2 C3 C4 125(3) 3_566 3_566 ?
C4 C3 C4 141(4) 9_666 3_566 ?
N2 C3 C4 19(3) . 3_566 ?
C2 C3 C4 106.2(18) . 3_566 ?
C2 C3 C4 18.4(19) 9_666 3_566 ?
N3 C3 C4 167(5) 9_666 11_655 ?
C3 C3 C4 120.1(8) 11_655 11_655 ?
N2 C3 C4 50(4) 11_655 11_655 ?
C2 C3 C4 16.0(18) 3_566 11_655 ?
C4 C3 C4 45(3) 9_666 11_655 ?
N2 C3 C4 114(3) . 11_655 ?
C2 C3 C4 12(2) . 11_655 ?
C2 C3 C4 94.7(17) 9_666 11_655 ?
C4 C3 C4 109.6(17) 3_566 11_655 ?
N3 C3 C2 89(5) 9_666 11_655 ?
C3 C3 C2 42.1(9) 11_655 11_655 ?
N2 C3 C2 128(5) 11_655 11_655 ?
C2 C3 C2 95(3) 3_566 11_655 ?
C4 C3 C2 116(3) 9_666 11_655 ?
N2 C3 C2 39(3) . 11_655 ?
C2 C3 C2 76.6(16) . 11_655 ?
C2 C3 C2 18.4(18) 9_666 11_655 ?
C4 C3 C2 30.6(18) 3_566 11_655 ?
C4 C3 C2 79.1(13) 11_655 11_655 ?
N3 C3 C3 137(5) 9_666 3_566 ?
C3 C3 C3 90.000(4) 11_655 3_566 ?
N2 C3 C3 81(5) 11_655 3_566 ?
C2 C3 C3 47(2) 3_566 3_566 ?
C4 C3 C3 71(3) 9_666 3_566 ?
N2 C3 C3 85(2) . 3_566 ?
C2 C3 C3 29.1(12) . 3_566 ?
C2 C3 C3 65.0(15) 9_666 3_566 ?
C4 C3 C3 78.4(14) 3_566 3_566 ?
C4 C3 C3 31.4(9) 11_655 3_566 ?
C2 C3 C3 48.1(10) 11_655 3_566 ?
N3 C3 H3A 68.9 9_666 . ?
C3 C3 H3A 115.9 11_655 . ?
N2 C3 H3A 74.7 11_655 . ?
C2 C3 H3A 107.6 3_566 . ?
C4 C3 H3A 84.0 9_666 . ?
N2 C3 H3A 120.5 . . ?
C2 C3 H3A 125.1 . . ?
C2 C3 H3A 141.0 9_666 . ?
C4 C3 H3A 126.8 3_566 . ?
C4 C3 H3A 123.5 11_655 . ?
C2 C3 H3A 157.4 11_655 . ?
C3 C3 H3A 154.1 3_566 . ?
C2 C4 N2 60(7) 11_655 3_566 ?
C2 C4 C2 39(8) 11_655 9_666 ?
N2 C4 C2 99(10) 3_566 9_666 ?
C2 C4 C3 68(3) 11_655 9_666 ?
N2 C4 C3 45(5) 3_566 9_666 ?
C2 C4 C3 93(4) 9_666 9_666 ?
C2 C4 C4 37(3) 11_655 3_566 ?
N2 C4 C4 93(9) 3_566 3_566 ?
C2 C4 C4 19(2) 9_666 3_566 ?
C3 C4 C4 102(3) 9_666 3_566 ?
C2 C4 N2 48(7) 11_655 . ?
N2 C4 N2 108(9) 3_566 . ?
C2 C4 N2 9(2) 9_666 . ?
C3 C4 N2 100(3) 9_666 . ?
C4 C4 N2 22(2) 3_566 . ?
C2 C4 N3 79(2) 11_655 . ?
N2 C4 N3 49(4) 3_566 . ?
C2 C4 N3 103(3) 9_666 . ?
C3 C4 N3 11(3) 9_666 . ?
C4 C4 N3 113(2) 3_566 . ?
N2 C4 N3 110(3) . . ?
C2 C4 C3 66(3) 11_655 3_566 ?
N2 C4 C3 53(5) 3_566 3_566 ?
C2 C4 C3 86(3) 9_666 3_566 ?
C3 C4 C3 10.0(12) 9_666 3_566 ?
C4 C4 C3 97.4(18) 3_566 3_566 ?
N2 C4 C3 93(3) . 3_566 ?
N3 C4 C3 17.4(14) . 3_566 ?
C2 C4 C3 35(7) 11_655 11_655 ?
N2 C4 C3 91(8) 3_566 11_655 ?
C2 C4 C3 16(2) 9_666 11_655 ?
C3 C4 C3 78(3) 9_666 11_655 ?
C4 C4 C3 32.6(10) 3_566 11_655 ?
N2 C4 C3 22(2) . 11_655 ?
N3 C4 C3 87.7(17) . 11_655 ?
C3 C4 C3 70.4(17) 3_566 11_655 ?
C2 C4 H4A 134.4 11_655 . ?
N2 C4 H4A 103.4 3_566 . ?
C2 C4 H4A 131.4 9_666 . ?
C3 C4 H4A 132.3 9_666 . ?
C4 C4 H4A 116.3 3_566 . ?
N2 C4 H4A 126.0 . . ?
N3 C4 H4A 123.9 . . ?
C3 C4 H4A 141.1 3_566 . ?
C3 C4 H4A 147.4 11_655 . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C2 N2 C4 58(7) 9_666 3_566 ?
C2 N2 C3 95(7) 9_666 11_655 ?
C4 N2 C3 102(8) 3_566 11_655 ?
C2 N2 C2 5(7) 9_666 11_655 ?
C4 N2 C2 53(9) 3_566 11_655 ?
C3 N2 C2 94(6) 11_655 11_655 ?
C2 N2 N3 111(5) 9_666 9_666 ?
C4 N2 N3 110(6) 3_566 9_666 ?
C3 N2 N3 16(4) 11_655 9_666 ?
C2 N2 N3 110(3) 11_655 9_666 ?
C2 N2 C3 92(5) 9_666 . ?
C4 N2 C3 108(7) 3_566 . ?
C3 N2 C3 9(2) 11_655 . ?
C2 N2 C3 92(4) 11_655 . ?
N3 N2 C3 20.5(15) 9_666 . ?
C2 N2 C4 16(5) 9_666 . ?
C4 N2 C4 65(8) 3_566 . ?
C3 N2 C4 108(6) 11_655 . ?
C2 N2 C4 20(3) 11_655 . ?
N3 N2 C4 124(3) 9_666 . ?
C3 N2 C4 104(4) . . ?
C2 N2 N2 3(5) 9_666 3_566 ?
C4 N2 N2 54(8) 3_566 3_566 ?
C3 N2 N2 95(5) 11_655 3_566 ?
C2 N2 N2 2(2) 11_655 3_566 ?
N3 N2 N2 110(2) 9_666 3_566 ?
C3 N2 N2 92(3) . 3_566 ?
C4 N2 N2 18(2) . 3_566 ?
C2 N2 C3 21(4) 9_666 9_666 ?
C4 N2 C3 72(8) 3_566 9_666 ?
C3 N2 C3 77(5) 11_655 9_666 ?
C2 N2 C3 22.5(17) 11_655 9_666 ?
N3 N2 C3 92(2) 9_666 9_666 ?
C3 N2 C3 73(3) . 9_666 ?
C4 N2 C3 31.1(15) . 9_666 ?
N2 N2 C3 22.3(15) 3_566 9_666 ?
C2 N2 H2B 137.5 9_666 . ?
C4 N2 H2B 94.9 3_566 . ?
C3 N2 H2B 124.0 11_655 . ?
C2 N2 H2B 136.6 11_655 . ?
N3 N2 H2B 108.8 9_666 . ?
C3 N2 H2B 128.9 . . ?
C4 N2 H2B 127.4 . . ?
N2 N2 H2B 136.5 3_566 . ?
C3 N2 H2B 158.0 9_666 . ?
C3 N3 C3 86(9) 9_666 3_566 ?
C3 N3 N2 23(6) 9_666 3_566 ?
C3 N3 N2 106(5) 3_566 3_566 ?
C3 N3 N2 106(5) 9_666 9_666 ?
C3 N3 N2 23(6) 3_566 9_666 ?
N2 N3 N2 124(5) 3_566 9_666 ?
C3 N3 C2 88(5) 9_666 . ?
C3 N3 C2 2(5) 3_566 . ?
N2 N3 C2 108(3) 3_566 . ?
N2 N3 C2 20.3(19) 9_666 . ?
C3 N3 C2 2(5) 9_666 11_655 ?
C3 N3 C2 88(5) 3_566 11_655 ?
N2 N3 C2 20.3(19) 3_566 11_655 ?
N2 N3 C2 108(3) 9_666 11_655 ?
C2 N3 C2 90(3) . 11_655 ?
C3 N3 C4 22(5) 9_666 . ?
C3 N3 C4 104(6) 3_566 . ?
N2 N3 C4 21(3) 3_566 . ?
N2 N3 C4 126.3(18) 9_666 . ?
C2 N3 C4 107(3) . . ?
C2 N3 C4 20.9(19) 11_655 . ?
C3 N3 C4 104(6) 9_666 11_655 ?
C3 N3 C4 22(5) 3_566 11_655 ?
N2 N3 C4 126.3(18) 3_566 11_655 ?
N2 N3 C4 21(3) 9_666 11_655 ?
C2 N3 C4 20.9(19) . 11_655 ?
C2 N3 C4 107(3) 11_655 11_655 ?
C4 N3 C4 120(4) . 11_655 ?
C3 N3 C2 13(5) 9_666 9_666 ?
C3 N3 C2 76(5) 3_566 9_666 ?
N2 N3 C2 35(2) 3_566 9_666 ?
N2 N3 C2 98(3) 9_666 9_666 ?
C2 N3 C2 78(2) . 9_666 ?
C2 N3 C2 15(2) 11_655 9_666 ?
C4 N3 C2 29(2) . 9_666 ?
C4 N3 C2 93(2) 11_655 9_666 ?
C3 N3 C2 76(5) 9_666 3_566 ?
C3 N3 C2 13(5) 3_566 3_566 ?
N2 N3 C2 98(3) 3_566 3_566 ?
N2 N3 C2 35(2) 9_666 3_566 ?
C2 N3 C2 15(2) . 3_566 ?
C2 N3 C2 78(2) 11_655 3_566 ?
C4 N3 C2 93(2) . 3_566 ?
C4 N3 C2 29(2) 11_655 3_566 ?
C2 N3 C2 65.1(18) 9_666 3_566 ?
C3 N3 H3B 145.3 9_666 . ?
C3 N3 H3B 127.6 3_566 . ?
N2 N3 H3B 122.8 3_566 . ?
N2 N3 H3B 105.5 9_666 . ?
C2 N3 H3B 125.3 . . ?
C2 N3 H3B 142.9 11_655 . ?
C4 N3 H3B 128.0 . . ?
C4 N3 H3B 110.3 11_655 . ?
C2 N3 H3B 156.4 9_666 . ?
C2 N3 H3B 138.5 3_566 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 C2 C3 N2 0(3) . . . . ?
C4 N3 C2 C3 0(3) . . . . ?
N2 C4 N3 C2 0(2) . . . . ?
C3 N2 C4 N3 -1(2) . . . . ?
C2 C3 N2 C4 1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A Cl1 0.86 2.56 3.346(3) 152.3 1_545
N1 H1B S1 0.86 2.55 3.403(3) 175.0 13_657

_refine_diff_density_max         1.042
_refine_diff_density_min         -1.066
_refine_diff_density_rms         0.074

####################################################################### 
# 
# 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_123K
_database_code_depnum_ccdc_archive 'CCDC 1437664'
_audit_update_record             
;
2016-01-30 deposited with the CCDC.
2016-02-05 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         'C3 H5 N2, 2(C H4 N2 S), Cl'
_chemical_formula_sum            'C5 H13 Cl N6 S2'
_chemical_formula_weight         256.78

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   14.674(9)
_cell_length_b                   9.779(6)
_cell_length_c                   8.412(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1207.1(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3736
_cell_measurement_theta_min      3.1919
_cell_measurement_theta_max      27.4816

_exptl_crystal_description       needlelike
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.638
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?

_exptl_absorpt_correction_T_min  0.7322
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_type   Multi-scan

_exptl_absorpt_process_details   
;   Higashi, T.(1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            12869
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.791
_diffrn_reflns_theta_max         27.448
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2741
_reflns_number_gt                2558
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0389P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.47(13)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2741
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0822
_refine_ls_wR_factor_gt          0.0806
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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 0.42808(15) 0.6861(2) 0.7462(3) 0.0153(5) Uani 1 1 d . . . . .
C2 C 0.06342(15) 0.6687(2) 0.7562(4) 0.0142(5) Uani 1 1 d . . . . .
C3 C 0.3478(2) 0.0490(4) 0.9914(4) 0.0396(8) Uani 1 1 d . . . . .
H3C H 0.4071 0.0818 0.9834 0.048 Uiso 1 1 calc R U . . .
C4 C 0.2309(3) -0.0814(4) 1.0430(4) 0.0407(9) Uani 1 1 d . . . . .
H4C H 0.1959 -0.1552 1.0765 0.049 Uiso 1 1 calc R U . . .
C5 C 0.2004(3) 0.0349(4) 0.9762(4) 0.0426(9) Uani 1 1 d . . . . .
H5A H 0.1401 0.0578 0.9554 0.051 Uiso 1 1 calc R U . . .
Cl1 Cl 0.25044(3) 0.40166(5) 0.76383(7) 0.01785(16) Uani 1 1 d . . . . .
N1 N 0.39565(15) 0.6362(3) 0.8817(2) 0.0191(6) Uani 1 1 d . . . . .
H1A H 0.3498 0.5814 0.8806 0.023 Uiso 1 1 calc R U . . .
H1B H 0.4205 0.6587 0.9705 0.023 Uiso 1 1 calc R U . . .
N2 N 0.38686(16) 0.6476(3) 0.6129(2) 0.0202(6) Uani 1 1 d . . . . .
H2A H 0.3412 0.5926 0.6167 0.024 Uiso 1 1 calc R U . . .
H2B H 0.4059 0.6777 0.5227 0.024 Uiso 1 1 calc R U . . .
N3 N 0.10181(15) 0.6311(3) 0.8923(2) 0.0202(6) Uani 1 1 d . . . . .
H3A H 0.1495 0.5800 0.8916 0.024 Uiso 1 1 calc R U . . .
H3B H 0.0790 0.6579 0.9812 0.024 Uiso 1 1 calc R U . . .
N4 N 0.10089(15) 0.6251(3) 0.6222(2) 0.0179(6) Uani 1 1 d . . . . .
H4A H 0.1486 0.5740 0.6252 0.021 Uiso 1 1 calc R U . . .
H4B H 0.0775 0.6478 0.5322 0.021 Uiso 1 1 calc R U . . .
N5 N 0.2743(2) 0.1113(3) 0.9456(3) 0.0416(8) Uani 1 1 d . . . . .
H5B H 0.2731 0.1907 0.9017 0.050 Uiso 1 1 calc R U . . .
N6 N 0.3225(2) -0.0697(3) 1.0516(3) 0.0372(7) Uani 1 1 d . . . . .
H6A H 0.3588 -0.1302 1.0903 0.045 Uiso 1 1 calc R U . . .
S1 S 0.51846(5) 0.79571(7) 0.74375(9) 0.0272(2) Uani 1 1 d . . . . .
S2 S -0.03110(4) 0.77192(6) 0.75256(9) 0.01835(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 N1 1.328(3) . ?
C1 N2 1.329(3) . ?
C1 S1 1.706(2) . ?
C2 N4 1.325(3) . ?
C2 N3 1.328(3) . ?
C2 S2 1.715(2) . ?
C3 N5 1.297(4) . ?
C3 N6 1.319(5) . ?
C4 C5 1.344(5) . ?
C4 N6 1.352(4) . ?
C5 N5 1.342(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N2 117.2(2) . . ?
N1 C1 S1 121.3(2) . . ?
N2 C1 S1 121.4(2) . . ?
N4 C2 N3 117.9(2) . . ?
N4 C2 S2 120.7(2) . . ?
N3 C2 S2 121.4(2) . . ?
N5 C3 N6 107.1(3) . . ?
C5 C4 N6 106.4(3) . . ?
N5 C5 C4 106.4(3) . . ?
C3 N5 C5 110.7(3) . . ?
C3 N6 C4 109.5(3) . . ?

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
N6 C4 C5 N5 0.7(4) . . . . ?
N6 C3 N5 C5 0.5(4) . . . . ?
C4 C5 N5 C3 -0.7(4) . . . . ?
N5 C3 N6 C4 0.0(4) . . . . ?
C5 C4 N6 C3 -0.4(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A Cl1 0.86 2.49 3.284(3) 154.6 .
N1 H1B S2 0.86 2.53 3.381(3) 171.3 4_567
N2 H2A Cl1 0.86 2.61 3.377(3) 149.8 .
N2 H2B S2 0.86 2.54 3.394(3) 171.0 4_566
N3 H3A Cl1 0.86 2.53 3.311(3) 151.7 .
N3 H3B S1 0.86 2.52 3.373(3) 172.0 4_467
N4 H4A Cl1 0.86 2.54 3.318(3) 151.5 .
N4 H4B S1 0.86 2.54 3.397(3) 175.5 4_466
N5 H5B Cl1 0.86 2.39 3.244(3) 172.1 .
N6 H6A S2 0.86 2.51 3.352(3) 168.3 4_557

_refine_diff_density_max         0.384
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.087




# start Validation Reply Form
_vrf_PLAT111_123K                
;
PROBLEM: ADDSYM Detects New (Pseudo) Centre of Symmetry .        100 %Fit  
RESPONSE:The systematic absence exceptions of the data solely gives 
          the P212121 space group by running XPREP.
;
_vrf_PLAT112_123K                
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem.        C        100 %Fit  
RESPONSE: It is inconsistent with the observed systematic absences, 
as the C centering is certainly absent.
;
_vrf_PLAT113_123K                
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group       Cmcm Check 
RESPONSE:It is inconsistent with the observed systematic absences, 
as the C centering is certainly absent.
;
_vrf_PLAT110_123K                
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check
RESPONSE: The systematic absence exceptions of the data solely gives 
          the P212121 space group by running XPREP.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_143K
_database_code_depnum_ccdc_archive 'CCDC 1445366'
_audit_update_record             
;
2016-01-30 deposited with the CCDC.
2016-02-05 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         'C3 H5 N2, 2(C H4 N2 S), Cl'
_chemical_formula_sum            'C5 H13 Cl N6 S2'
_chemical_formula_weight         256.78

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      orthorhombic
_space_group_IT_number           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'

_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+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   14.700(13)
_cell_length_b                   9.771(8)
_cell_length_c                   8.414(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1208.5(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    3009
_cell_measurement_theta_min      3.1935
_cell_measurement_theta_max      27.5049

_exptl_crystal_description       needlelike
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_F_000             536.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2000
_exptl_crystal_size_mid          0.2000
_exptl_crystal_size_min          0.2000
_exptl_absorpt_coefficient_mu    0.637
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan

_exptl_absorpt_process_details   
;   Higashi, T.(1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan. 
;
_exptl_absorpt_correction_T_min  0.8856
_exptl_absorpt_correction_T_max  1.0000

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            6406
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.483
_diffrn_reflns_theta_max         27.440
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             1377
_reflns_number_gt                1329
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.996

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0366P)²+2.3246P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 516 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.34(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1377
_refine_ls_number_parameters     87
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0893
_refine_ls_wR_factor_gt          0.0885
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.084
_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 0.68259(17) 0.6765(3) 0.7546(6) 0.0197(5) Uani 1 1 d . . . . .
C2 C 0.9025(9) 0.4506(15) 1.0047(16) 0.039(3) Uani 0.5 1 d D . P . .
H2C H 0.8413 0.4172 1.0133 0.047 Uiso 0.5 1 d R U P . .
C3 C 1.0563(11) 0.4628(15) 1.0252(19) 0.050(4) Uani 0.5 1 d D . P . .
H3A H 1.1179 0.4396 1.0523 0.060 Uiso 0.5 1 d R U P . .
C4 C 1.0234(8) 0.5761(17) 0.9545(18) 0.038(4) Uani 0.5 1 d D . P . .
H4A H 1.0607 0.6501 0.9170 0.046 Uiso 0.5 1 d R U P . .
Cl1 Cl 1.0000 0.90122(8) 0.7500 0.0231(2) Uani 1 2 d S T P . .
N1 N 0.6432(2) 0.6388(5) 0.8893(4) 0.0264(10) Uani 1 1 d . . . . .
H1A H 0.5961 0.5865 0.8872 0.032 Uiso 1 1 d R U . . .
H1B H 0.6646 0.6666 0.9787 0.032 Uiso 1 1 d R U . . .
N2 N 0.6471(2) 0.6310(5) 0.6198(4) 0.0226(9) Uani 1 1 d . . . . .
H2A H 0.6000 0.5788 0.6217 0.027 Uiso 1 1 d R U . . .
H2B H 0.6711 0.6537 0.5305 0.027 Uiso 1 1 d R U . . .
N3 N 0.9798(9) 0.3890(13) 1.0505(15) 0.040(3) Uani 0.5 1 d D . P . .
H3B H 0.9799 0.3049 1.0943 0.048 Uiso 0.5 1 d R U P . .
N4 N 0.9323(9) 0.5728(14) 0.9432(13) 0.039(3) Uani 0.5 1 d D . P . .
H4B H 0.8963 0.6382 0.9017 0.047 Uiso 0.5 1 d R U P . .
S1 S 0.77588(5) 0.78149(9) 0.75351(14) 0.0317(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 N1 1.325(5) . ?
C1 N2 1.325(6) . ?
C1 S1 1.713(3) . ?
C2 N4 0.661(13) 4_567 ?
C2 C2 0.97(3) 4_567 ?
C2 N3 1.343(15) . ?
C2 N4 1.372(15) . ?
C2 C4 1.829(18) 4_567 ?
C3 C4 0.638(13) 4_567 ?
C3 C3 0.84(3) 4_567 ?
C3 C4 1.347(17) . ?
C3 N3 1.354(15) . ?
C3 N4 1.875(16) 4_567 ?
C3 N3 1.942(18) 4_567 ?
C4 C3 0.638(13) 4_567 ?
C4 N3 0.728(13) 4_567 ?
C4 N4 1.344(15) . ?
C4 C4 1.67(3) 4_567 ?
C4 C2 1.829(18) 4_567 ?
N3 C4 0.728(13) 4_567 ?
N3 N4 0.794(14) 4_567 ?
N3 C3 1.942(18) 4_567 ?
N4 C2 0.661(13) 4_567 ?
N4 N3 0.794(14) 4_567 ?
N4 N4 1.71(3) 4_567 ?
N4 C3 1.875(16) 4_567 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N2 117.8(2) . . ?
N1 C1 S1 121.4(3) . . ?
N2 C1 S1 120.8(3) . . ?
N4 C2 C2 114(3) 4_567 4_567 ?
N4 C2 N3 24.9(18) 4_567 . ?
C2 C2 N3 118.1(11) 4_567 . ?
N4 C2 N4 110(3) 4_567 . ?
C2 C2 N4 26.2(8) 4_567 . ?
N3 C2 N4 103.2(14) . . ?
N4 C2 C4 35.1(18) 4_567 4_567 ?
C2 C2 C4 99.1(8) 4_567 4_567 ?
N3 C2 C4 19.9(8) . 4_567 ?
N4 C2 C4 83.4(11) . 4_567 ?
C4 C3 C3 130(3) 4_567 4_567 ?
C4 C3 C4 110(3) 4_567 . ?
C3 C3 C4 21.1(8) 4_567 . ?
C4 C3 N3 8.4(19) 4_567 . ?
C3 C3 N3 122.6(11) 4_567 . ?
C4 C3 N3 102.1(16) . . ?
C4 C3 N4 28(2) 4_567 4_567 ?
C3 C3 N4 103.4(6) 4_567 4_567 ?
C4 C3 N4 82.3(12) . 4_567 ?
N3 C3 N4 21.6(7) . 4_567 ?
C4 C3 N3 95(3) 4_567 4_567 ?
C3 C3 N3 35.9(5) 4_567 4_567 ?
C4 C3 N3 14.9(6) . 4_567 ?
N3 C3 N3 88.1(13) . 4_567 ?
N4 C3 N3 67.7(8) 4_567 4_567 ?
C3 C4 N3 164(4) 4_567 4_567 ?
C3 C4 N4 139(3) 4_567 . ?
N3 C4 N4 29.4(13) 4_567 . ?
C3 C4 C3 28(2) 4_567 . ?
N3 C4 C3 137(2) 4_567 . ?
N4 C4 C3 111.7(15) . . ?
C3 C4 C4 49(3) 4_567 4_567 ?
N3 C4 C4 116.3(15) 4_567 4_567 ?
N4 C4 C4 90.6(9) . 4_567 ?
C3 C4 C4 21.1(8) . 4_567 ?
C3 C4 C2 127(3) 4_567 4_567 ?
N3 C4 C2 38.9(14) 4_567 4_567 ?
N4 C4 C2 16.4(7) . 4_567 ?
C3 C4 C2 98.5(12) . 4_567 ?
C4 C4 C2 77.7(7) 4_567 4_567 ?
C4 N3 N4 124(2) 4_567 4_567 ?
C4 N3 C2 121(2) 4_567 . ?
N4 N3 C2 20.5(13) 4_567 . ?
C4 N3 C3 7.3(17) 4_567 . ?
N4 N3 C3 119.4(19) 4_567 . ?
C2 N3 C3 114.8(16) . . ?
C4 N3 C3 28.4(15) 4_567 4_567 ?
N4 N3 C3 100.4(15) 4_567 4_567 ?
C2 N3 C3 93.5(11) . 4_567 ?
C3 N3 C3 21.4(9) . 4_567 ?
C2 N4 N3 135(3) 4_567 4_567 ?
C2 N4 C4 128(2) 4_567 . ?
N3 N4 C4 26.7(13) 4_567 . ?
C2 N4 C2 40(2) 4_567 . ?
N3 N4 C2 131.7(18) 4_567 . ?
C4 N4 C2 108.2(13) . . ?
C2 N4 N4 49(2) 4_567 4_567 ?
N3 N4 N4 110.7(14) 4_567 4_567 ?
C4 N4 N4 88.9(9) . 4_567 ?
C2 N4 N4 21.3(7) . 4_567 ?
C2 N4 C3 119(2) 4_567 4_567 ?
N3 N4 C3 39.0(13) 4_567 4_567 ?
C4 N4 C3 12.8(10) . 4_567 ?
C2 N4 C3 95.5(11) . 4_567 ?
N4 N4 C3 76.5(6) 4_567 4_567 ?

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
C4 C3 C4 C3 -171(7) 4_567 . . 4_567 ?
N3 C3 C4 C3 -168(6) . . . 4_567 ?
N4 C3 C4 C3 -176(6) 4_567 . . 4_567 ?
N3 C3 C4 C3 171(6) 4_567 . . 4_567 ?
C4 C3 C4 N3 17(3) 4_567 . . 4_567 ?
C3 C3 C4 N3 -171(6) 4_567 . . 4_567 ?
N3 C3 C4 N3 21(4) . . . 4_567 ?
N4 C3 C4 N3 12(3) 4_567 . . 4_567 ?
C4 C3 C4 N4 -2(2) 4_567 . . . ?
C3 C3 C4 N4 170(5) 4_567 . . . ?
N3 C3 C4 N4 2.1(18) . . . . ?
N4 C3 C4 N4 -6.7(14) 4_567 . . . ?
N3 C3 C4 N4 -19(3) 4_567 . . . ?
C3 C3 C4 C4 171(7) 4_567 . . 4_567 ?
N3 C3 C4 C4 4(2) . . . 4_567 ?
N4 C3 C4 C4 -5(2) 4_567 . . 4_567 ?
N3 C3 C4 C4 -17(3) 4_567 . . 4_567 ?
C4 C3 C4 C2 9(2) 4_567 . . 4_567 ?
C3 C3 C4 C2 -180(5) 4_567 . . 4_567 ?
N3 C3 C4 C2 12.3(15) . . . 4_567 ?
N4 C3 C4 C2 3.5(8) 4_567 . . 4_567 ?
N3 C3 C4 C2 -9(3) 4_567 . . 4_567 ?
N4 C2 N3 C4 -104(4) 4_567 . . 4_567 ?
C2 C2 N3 C4 -18(3) 4_567 . . 4_567 ?
N4 C2 N3 C4 5(3) . . . 4_567 ?
C2 C2 N3 N4 86(5) 4_567 . . 4_567 ?
N4 C2 N3 N4 109(4) . . . 4_567 ?
C4 C2 N3 N4 104(4) 4_567 . . 4_567 ?
N4 C2 N3 C3 -108(4) 4_567 . . . ?
C2 C2 N3 C3 -22(3) 4_567 . . . ?
N4 C2 N3 C3 0.9(16) . . . . ?
C4 C2 N3 C3 -3.9(19) 4_567 . . . ?
N4 C2 N3 C3 -111(4) 4_567 . . 4_567 ?
C2 C2 N3 C3 -25(2) 4_567 . . 4_567 ?
N4 C2 N3 C3 -1.7(11) . . . 4_567 ?
C4 C2 N3 C3 -7(2) 4_567 . . 4_567 ?
C3 C3 N3 C4 -160(15) 4_567 . . 4_567 ?
C4 C3 N3 C4 -154(13) . . . 4_567 ?
N4 C3 N3 C4 -130(14) 4_567 . . 4_567 ?
N3 C3 N3 C4 -149(14) 4_567 . . 4_567 ?
C4 C3 N3 N4 130(14) 4_567 . . 4_567 ?
C3 C3 N3 N4 -30(4) 4_567 . . 4_567 ?
C4 C3 N3 N4 -24(2) . . . 4_567 ?
N3 C3 N3 N4 -19.0(17) 4_567 . . 4_567 ?
C4 C3 N3 C2 153(14) 4_567 . . . ?
C3 C3 N3 C2 -7(4) 4_567 . . . ?
C4 C3 N3 C2 -1.8(18) . . . . ?
N4 C3 N3 C2 22.5(16) 4_567 . . . ?
N3 C3 N3 C2 3.5(11) 4_567 . . . ?
C4 C3 N3 C3 160(15) 4_567 . . 4_567 ?
C4 C3 N3 C3 5(2) . . . 4_567 ?
N4 C3 N3 C3 30(4) 4_567 . . 4_567 ?
N3 C3 N3 C3 11(3) 4_567 . . 4_567 ?
C3 C4 N4 C2 46(6) 4_567 . . 4_567 ?
N3 C4 N4 C2 -115(4) 4_567 . . 4_567 ?
C3 C4 N4 C2 38(4) . . . 4_567 ?
C4 C4 N4 C2 38(4) 4_567 . . 4_567 ?
C3 C4 N4 N3 160(6) 4_567 . . 4_567 ?
C3 C4 N4 N3 153(3) . . . 4_567 ?
C4 C4 N4 N3 152(4) 4_567 . . 4_567 ?
C2 C4 N4 N3 115(4) 4_567 . . 4_567 ?
C3 C4 N4 C2 6(4) 4_567 . . . ?
N3 C4 N4 C2 -155(3) 4_567 . . . ?
C3 C4 N4 C2 -1.7(16) . . . . ?
C4 C4 N4 C2 -2.3(15) 4_567 . . . ?
C2 C4 N4 C2 -40(3) 4_567 . . . ?
C3 C4 N4 N4 15(4) 4_567 . . 4_567 ?
N3 C4 N4 N4 -146(3) 4_567 . . 4_567 ?
C3 C4 N4 N4 7.3(15) . . . 4_567 ?
C4 C4 N4 N4 6.7(13) 4_567 . . 4_567 ?
C2 C4 N4 N4 -31(3) 4_567 . . 4_567 ?
N3 C4 N4 C3 -160(6) 4_567 . . 4_567 ?
C3 C4 N4 C3 -7(4) . . . 4_567 ?
C4 C4 N4 C3 -8(3) 4_567 . . 4_567 ?
C2 C4 N4 C3 -46(6) 4_567 . . 4_567 ?
N4 C2 N4 C2 -103(5) 4_567 . . 4_567 ?
N3 C2 N4 C2 -128(3) . . . 4_567 ?
C4 C2 N4 C2 -127(3) 4_567 . . 4_567 ?
N4 C2 N4 N3 11(3) 4_567 . . 4_567 ?
C2 C2 N4 N3 114(4) 4_567 . . 4_567 ?
N3 C2 N4 N3 -14(2) . . . 4_567 ?
C4 C2 N4 N3 -12.8(19) 4_567 . . 4_567 ?
N4 C2 N4 C4 26(2) 4_567 . . . ?
C2 C2 N4 C4 129(3) 4_567 . . . ?
N3 C2 N4 C4 0.5(13) . . . . ?
C4 C2 N4 C4 2.1(14) 4_567 . . . ?
C2 C2 N4 N4 103(5) 4_567 . . 4_567 ?
N3 C2 N4 N4 -25(2) . . . 4_567 ?
C4 C2 N4 N4 -23(2) 4_567 . . 4_567 ?
N4 C2 N4 C3 27(2) 4_567 . . 4_567 ?
C2 C2 N4 C3 130(3) 4_567 . . 4_567 ?
N3 C2 N4 C3 1.8(11) . . . 4_567 ?
C4 C2 N4 C3 3.4(8) 4_567 . . 4_567 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A Cl1 0.86 2.57 3.345(4) 150.4 5_445
N1 H1B S1 0.86 2.52 3.379(4) 172.9 6_665
N2 H2A Cl1 0.86 2.52 3.304(4) 152.5 5_445
N2 H2B S1 0.86 2.54 3.393(4) 173.5 6_664
N3 H3B Cl1 0.90 2.42 3.308(13) 168.8 2_765
N4 H4B S1 0.90 2.58 3.463(12) 167.5 .

_refine_diff_density_max         1.111
_refine_diff_density_min         -0.911
_refine_diff_density_rms         0.065

