# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_e999a
_database_code_depnum_ccdc_archive 'CCDC 1528387'
_audit_update_record             
;
2017-01-18 deposited with the CCDC.
2017-06-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H28 Cl2 N8 Pt'
_chemical_formula_sum            'C20 H28 Cl2 N8 Pt'
_chemical_formula_weight         646.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pt Pt -1.7033 8.3905 '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                   10.5079(3)
_cell_length_b                   12.9149(4)
_cell_length_c                   19.0193(7)
_cell_angle_alpha                90
_cell_angle_beta                 104.295(4)
_cell_angle_gamma                90
_cell_volume                     2501.15(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9305
_cell_measurement_theta_min      1.9947
_cell_measurement_theta_max      28.4547

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.379
_exptl_crystal_size_mid          0.245
_exptl_crystal_size_min          0.212
_exptl_absorpt_coefficient_mu    5.847
_shelx_estimated_absorpt_T_min   0.215
_shelx_estimated_absorpt_T_max   0.370
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.208
_exptl_absorpt_correction_T_max  0.363
_exptl_absorpt_process_details   'Rigaku OD CrysAlis Pro'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Oxford Sapphire CCD'
_diffrn_measurement_method       θ/2θ
_diffrn_detector_area_resol_mean 8.2564
_diffrn_reflns_number            17002
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.547
_diffrn_reflns_theta_max         28.482
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5728
_reflns_number_gt                4408
_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       'Rigaku OD CrysAlisPro 1.171.38.43'
_computing_cell_refinement       'Rigaku OD CrysAlisPro 1.171.38.43'
_computing_data_reduction        'Rigaku OD CrysAlisPro 1.171.38.43'
_computing_structure_solution    'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'CIFTAB (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)+(0.0246P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     patterson
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5728
_refine_ls_number_parameters     284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0244
_refine_ls_wR_factor_ref         0.0488
_refine_ls_wR_factor_gt          0.0469
_refine_ls_goodness_of_fit_ref   0.946
_refine_ls_restrained_S_all      0.946
_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
Pt1 Pt 0.68366(2) 0.11952(2) 0.22787(2) 0.03252(5) Uani 1 1 d . . . . .
Cl1 Cl 0.83708(8) 0.18144(7) 0.17145(5) 0.0467(2) Uani 1 1 d . . . . .
Cl2 Cl 0.83823(9) 0.09742(8) 0.33474(5) 0.0541(3) Uani 1 1 d . . . . .
N1 N 0.4177(3) 0.1991(2) 0.03134(16) 0.0406(7) Uani 1 1 d . . . . .
C2 C 0.5102(3) 0.2156(2) 0.08996(19) 0.0399(8) Uani 1 1 d . . . . .
H2A H 0.5484 0.2803 0.1012 0.048 Uiso 1 1 calc R U . . .
N3 N 0.5469(2) 0.13234(18) 0.13328(14) 0.0314(6) Uani 1 1 d . . . . .
C3A C 0.4708(3) 0.0550(2) 0.09882(18) 0.0323(7) Uani 1 1 d . . . . .
N4 N 0.4694(3) -0.0438(2) 0.11950(15) 0.0380(7) Uani 1 1 d . . . . .
C5 C 0.3858(3) -0.1040(2) 0.0740(2) 0.0423(8) Uani 1 1 d . . . . .
C51 C 0.3817(4) -0.2155(3) 0.0953(2) 0.0652(12) Uani 1 1 d . . . . .
H51A H 0.3181 -0.2518 0.0587 0.078 Uiso 1 1 calc R U . . .
H51B H 0.4667 -0.2461 0.1002 0.078 Uiso 1 1 calc R U . . .
H51C H 0.3576 -0.2200 0.1408 0.078 Uiso 1 1 calc R U . . .
C6 C 0.3050(3) -0.0665(3) 0.0079(2) 0.0411(8) Uani 1 1 d . . . . .
H6A H 0.2497 -0.1124 -0.0230 0.049 Uiso 1 1 calc R U . . .
C7 C 0.3060(3) 0.0346(2) -0.01176(19) 0.0357(8) Uani 1 1 d . . . . .
C71 C 0.2228(3) 0.0822(3) -0.0787(2) 0.0450(9) Uani 1 1 d . . . . .
H71A H 0.2316 0.0426 -0.1206 0.054 Uiso 1 1 calc R U . . .
H71B H 0.2536 0.1520 -0.0838 0.054 Uiso 1 1 calc R U . . .
C72 C 0.0775(4) 0.0860(3) -0.0771(2) 0.0600(12) Uani 1 1 d . . . . .
H72A H 0.0513 0.0162 -0.0664 0.072 Uiso 1 1 calc R U . . .
C73 C 0.0576(5) 0.1573(4) -0.0177(3) 0.0967(18) Uani 1 1 d . . . . .
H73A H -0.0346 0.1640 -0.0207 0.116 Uiso 1 1 calc R U . . .
H73B H 0.0938 0.2242 -0.0233 0.116 Uiso 1 1 calc R U . . .
H73C H 0.1010 0.1290 0.0287 0.116 Uiso 1 1 calc R U . . .
C74 C -0.0058(5) 0.1169(4) -0.1508(3) 0.107(2) Uani 1 1 d . . . . .
H74A H -0.0969 0.1065 -0.1521 0.128 Uiso 1 1 calc R U . . .
H74B H 0.0174 0.0752 -0.1875 0.128 Uiso 1 1 calc R U . . .
H74C H 0.0090 0.1886 -0.1595 0.128 Uiso 1 1 calc R U . . .
N8 N 0.3925(2) 0.09519(19) 0.03670(15) 0.0346(6) Uani 1 1 d . . . . .
N11 N 0.4436(3) -0.0447(2) 0.33566(18) 0.0501(8) Uani 1 1 d . . . . .
C12 C 0.5504(4) -0.0207(3) 0.3155(2) 0.0546(11) Uani 1 1 d . . . . .
H12A H 0.6260 -0.0610 0.3285 0.066 Uiso 1 1 calc R U . . .
N13 N 0.5446(2) 0.0655(2) 0.27509(15) 0.0360(6) Uani 1 1 d . . . . .
C13A C 0.4215(3) 0.1000(2) 0.26792(18) 0.0325(7) Uani 1 1 d . . . . .
N14 N 0.3633(3) 0.1829(2) 0.23223(17) 0.0429(7) Uani 1 1 d . . . . .
C15 C 0.2395(3) 0.1977(3) 0.2348(2) 0.0473(10) Uani 1 1 d . . . . .
C151 C 0.1711(3) 0.2904(3) 0.1954(3) 0.0832(17) Uani 1 1 d . . . . .
H15A H 0.0828 0.2933 0.2009 0.100 Uiso 1 1 calc R U . . .
H15B H 0.2173 0.3521 0.2152 0.100 Uiso 1 1 calc R U . . .
H15C H 0.1695 0.2852 0.1448 0.100 Uiso 1 1 calc R U . . .
C16 C 0.1727(3) 0.1308(2) 0.2720(2) 0.0446(9) Uani 1 1 d . . . . .
H16A H 0.0857 0.1446 0.2716 0.054 Uiso 1 1 calc R U . . .
C17 C 0.2328(3) 0.0463(2) 0.30848(18) 0.0339(7) Uani 1 1 d . . . . .
C171 C 0.1713(3) -0.0301(2) 0.34869(19) 0.0392(8) Uani 1 1 d . . . . .
H17A H 0.1964 -0.0990 0.3370 0.047 Uiso 1 1 calc R U . . .
H17B H 0.0767 -0.0247 0.3310 0.047 Uiso 1 1 calc R U . . .
C172 C 0.2050(6) -0.0194(4) 0.4295(3) 0.0892(17) Uani 1 1 d . . . . .
H17C H 0.2877 -0.0581 0.4400 0.107 Uiso 1 1 calc R U . . .
C173 C 0.1251(5) -0.0965(4) 0.4612(3) 0.0875(16) Uani 1 1 d . . . . .
H17D H 0.1375 -0.1648 0.4441 0.105 Uiso 1 1 calc R U . . .
H17E H 0.0338 -0.0785 0.4464 0.105 Uiso 1 1 calc R U . . .
H17F H 0.1536 -0.0951 0.5132 0.105 Uiso 1 1 calc R U . . .
C174 C 0.2478(11) 0.0619(7) 0.4642(4) 0.255(7) Uani 1 1 d . . . . .
H17G H 0.2732 0.1107 0.4321 0.307 Uiso 1 1 calc R U . . .
H17H H 0.3225 0.0452 0.5030 0.307 Uiso 1 1 calc R U . . .
H17I H 0.1803 0.0916 0.4839 0.307 Uiso 1 1 calc R U . . .
N18 N 0.3601(2) 0.03341(19) 0.30512(15) 0.0340(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
Pt1 N3 2.013(2) . ?
Pt1 N13 2.019(3) . ?
Pt1 Cl2 2.2849(9) . ?
Pt1 Cl1 2.2900(9) . ?
N1 C2 1.303(4) . ?
N1 N8 1.377(3) . ?
C2 N3 1.351(4) . ?
C2 H2A 0.9300 . ?
N3 C3A 1.345(4) . ?
C3A N4 1.336(4) . ?
C3A N8 1.365(4) . ?
N4 C5 1.323(4) . ?
C5 C6 1.417(5) . ?
C5 C51 1.500(4) . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
C6 C7 1.359(4) . ?
C6 H6A 0.9300 . ?
C7 N8 1.369(4) . ?
C7 C71 1.488(4) . ?
C71 C72 1.536(5) . ?
C71 H71A 0.9700 . ?
C71 H71B 0.9700 . ?
C72 C73 1.511(6) . ?
C72 C74 1.512(6) . ?
C72 H72A 0.9800 . ?
C73 H73A 0.9600 . ?
C73 H73B 0.9600 . ?
C73 H73C 0.9600 . ?
C74 H74A 0.9600 . ?
C74 H74B 0.9600 . ?
C74 H74C 0.9600 . ?
N11 C12 1.309(4) . ?
N11 N18 1.369(3) . ?
C12 N13 1.346(4) . ?
C12 H12A 0.9300 . ?
N13 C13A 1.343(4) . ?
C13A N14 1.332(4) . ?
C13A N18 1.372(4) . ?
N14 C15 1.328(4) . ?
C15 C16 1.409(5) . ?
C15 C151 1.498(5) . ?
C151 H15A 0.9600 . ?
C151 H15B 0.9600 . ?
C151 H15C 0.9600 . ?
C16 C17 1.362(4) . ?
C16 H16A 0.9300 . ?
C17 N18 1.364(4) . ?
C17 C171 1.490(4) . ?
C171 C172 1.497(5) . ?
C171 H17A 0.9700 . ?
C171 H17B 0.9700 . ?
C172 C174 1.262(7) . ?
C172 C173 1.520(6) . ?
C172 H17C 0.9800 . ?
C173 H17D 0.9600 . ?
C173 H17E 0.9600 . ?
C173 H17F 0.9600 . ?
C174 H17G 0.9600 . ?
C174 H17H 0.9600 . ?
C174 H17I 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
N3 Pt1 N13 89.47(10) . . ?
N3 Pt1 Cl2 177.54(7) . . ?
N13 Pt1 Cl2 89.70(8) . . ?
N3 Pt1 Cl1 88.98(7) . . ?
N13 Pt1 Cl1 178.45(8) . . ?
Cl2 Pt1 Cl1 91.86(3) . . ?
C2 N1 N8 102.2(3) . . ?
N1 C2 N3 115.7(3) . . ?
N1 C2 H2A 122.2 . . ?
N3 C2 H2A 122.2 . . ?
C3A N3 C2 104.3(3) . . ?
C3A N3 Pt1 125.6(2) . . ?
C2 N3 Pt1 130.1(2) . . ?
N4 C3A N3 127.9(3) . . ?
N4 C3A N8 124.8(3) . . ?
N3 C3A N8 107.3(3) . . ?
C5 N4 C3A 115.0(3) . . ?
N4 C5 C6 122.4(3) . . ?
N4 C5 C51 116.5(3) . . ?
C6 C5 C51 121.1(3) . . ?
C5 C51 H51A 109.5 . . ?
C5 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C5 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C7 C6 C5 121.9(3) . . ?
C7 C6 H6A 119.1 . . ?
C5 C6 H6A 119.1 . . ?
C6 C7 N8 114.4(3) . . ?
C6 C7 C71 126.1(3) . . ?
N8 C7 C71 119.5(3) . . ?
C7 C71 C72 111.9(3) . . ?
C7 C71 H71A 109.2 . . ?
C72 C71 H71A 109.2 . . ?
C7 C71 H71B 109.2 . . ?
C72 C71 H71B 109.2 . . ?
H71A C71 H71B 107.9 . . ?
C73 C72 C74 112.2(4) . . ?
C73 C72 C71 110.9(3) . . ?
C74 C72 C71 110.0(4) . . ?
C73 C72 H72A 107.9 . . ?
C74 C72 H72A 107.9 . . ?
C71 C72 H72A 107.9 . . ?
C72 C73 H73A 109.5 . . ?
C72 C73 H73B 109.5 . . ?
H73A C73 H73B 109.5 . . ?
C72 C73 H73C 109.5 . . ?
H73A C73 H73C 109.5 . . ?
H73B C73 H73C 109.5 . . ?
C72 C74 H74A 109.5 . . ?
C72 C74 H74B 109.5 . . ?
H74A C74 H74B 109.5 . . ?
C72 C74 H74C 109.5 . . ?
H74A C74 H74C 109.5 . . ?
H74B C74 H74C 109.5 . . ?
C3A N8 C7 121.6(3) . . ?
C3A N8 N1 110.5(2) . . ?
C7 N8 N1 127.9(3) . . ?
C12 N11 N18 102.0(3) . . ?
N11 C12 N13 116.2(3) . . ?
N11 C12 H12A 121.9 . . ?
N13 C12 H12A 121.9 . . ?
C13A N13 C12 103.8(3) . . ?
C13A N13 Pt1 128.7(2) . . ?
C12 N13 Pt1 127.2(2) . . ?
N14 C13A N13 128.9(3) . . ?
N14 C13A N18 123.4(3) . . ?
N13 C13A N18 107.7(3) . . ?
C15 N14 C13A 115.3(3) . . ?
N14 C15 C16 123.0(3) . . ?
N14 C15 C151 116.7(3) . . ?
C16 C15 C151 120.3(3) . . ?
C15 C151 H15A 109.5 . . ?
C15 C151 H15B 109.5 . . ?
H15A C151 H15B 109.5 . . ?
C15 C151 H15C 109.5 . . ?
H15A C151 H15C 109.5 . . ?
H15B C151 H15C 109.5 . . ?
C17 C16 C15 121.4(3) . . ?
C17 C16 H16A 119.3 . . ?
C15 C16 H16A 119.3 . . ?
C16 C17 N18 114.2(3) . . ?
C16 C17 C171 125.9(3) . . ?
N18 C17 C171 119.9(3) . . ?
C17 C171 C172 116.4(3) . . ?
C17 C171 H17A 108.2 . . ?
C172 C171 H17A 108.2 . . ?
C17 C171 H17B 108.2 . . ?
C172 C171 H17B 108.2 . . ?
H17A C171 H17B 107.4 . . ?
C174 C172 C171 125.2(5) . . ?
C174 C172 C173 119.9(5) . . ?
C171 C172 C173 109.5(4) . . ?
C174 C172 H17C 97.7 . . ?
C171 C172 H17C 97.7 . . ?
C173 C172 H17C 97.7 . . ?
C172 C173 H17D 109.5 . . ?
C172 C173 H17E 109.5 . . ?
H17D C173 H17E 109.5 . . ?
C172 C173 H17F 109.5 . . ?
H17D C173 H17F 109.5 . . ?
H17E C173 H17F 109.5 . . ?
C172 C174 H17G 109.5 . . ?
C172 C174 H17H 109.5 . . ?
H17G C174 H17H 109.5 . . ?
C172 C174 H17I 109.5 . . ?
H17G C174 H17I 109.5 . . ?
H17H C174 H17I 109.5 . . ?
C17 N18 N11 127.1(3) . . ?
C17 N18 C13A 122.6(3) . . ?
N11 N18 C13A 110.3(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
N8 N1 C2 N3 -0.5(4) . . . . ?
N1 C2 N3 C3A 0.3(4) . . . . ?
N1 C2 N3 Pt1 179.9(2) . . . . ?
C2 N3 C3A N4 179.8(3) . . . . ?
Pt1 N3 C3A N4 0.2(5) . . . . ?
C2 N3 C3A N8 0.1(3) . . . . ?
Pt1 N3 C3A N8 -179.48(19) . . . . ?
N3 C3A N4 C5 -178.6(3) . . . . ?
N8 C3A N4 C5 1.1(5) . . . . ?
C3A N4 C5 C6 0.7(5) . . . . ?
C3A N4 C5 C51 179.9(3) . . . . ?
N4 C5 C6 C7 -1.9(6) . . . . ?
C51 C5 C6 C7 179.0(4) . . . . ?
C5 C6 C7 N8 1.2(5) . . . . ?
C5 C6 C7 C71 -178.2(3) . . . . ?
C6 C7 C71 C72 68.9(5) . . . . ?
N8 C7 C71 C72 -110.5(4) . . . . ?
C7 C71 C72 C73 65.4(4) . . . . ?
C7 C71 C72 C74 -170.0(3) . . . . ?
N4 C3A N8 C7 -1.8(5) . . . . ?
N3 C3A N8 C7 177.9(3) . . . . ?
N4 C3A N8 N1 179.8(3) . . . . ?
N3 C3A N8 N1 -0.5(4) . . . . ?
C6 C7 N8 C3A 0.5(5) . . . . ?
C71 C7 N8 C3A 180.0(3) . . . . ?
C6 C7 N8 N1 178.6(3) . . . . ?
C71 C7 N8 N1 -1.9(5) . . . . ?
C2 N1 N8 C3A 0.6(3) . . . . ?
C2 N1 N8 C7 -177.7(3) . . . . ?
N18 N11 C12 N13 0.2(5) . . . . ?
N11 C12 N13 C13A -0.6(5) . . . . ?
N11 C12 N13 Pt1 -174.6(3) . . . . ?
C12 N13 C13A N14 -179.4(4) . . . . ?
Pt1 N13 C13A N14 -5.4(5) . . . . ?
C12 N13 C13A N18 0.7(4) . . . . ?
Pt1 N13 C13A N18 174.6(2) . . . . ?
N13 C13A N14 C15 -179.9(3) . . . . ?
N18 C13A N14 C15 0.0(5) . . . . ?
C13A N14 C15 C16 -0.4(5) . . . . ?
C13A N14 C15 C151 179.8(4) . . . . ?
N14 C15 C16 C17 0.6(6) . . . . ?
C151 C15 C16 C17 -179.7(4) . . . . ?
C15 C16 C17 N18 -0.3(5) . . . . ?
C15 C16 C17 C171 -179.2(3) . . . . ?
C16 C17 C171 C172 -102.1(5) . . . . ?
N18 C17 C171 C172 79.1(5) . . . . ?
C17 C171 C172 C174 21.2(10) . . . . ?
C17 C171 C172 C173 175.0(4) . . . . ?
C16 C17 N18 N11 -179.1(3) . . . . ?
C171 C17 N18 N11 -0.1(5) . . . . ?
C16 C17 N18 C13A -0.1(5) . . . . ?
C171 C17 N18 C13A 178.9(3) . . . . ?
C12 N11 N18 C17 179.4(3) . . . . ?
C12 N11 N18 C13A 0.3(4) . . . . ?
N14 C13A N18 C17 0.3(5) . . . . ?
N13 C13A N18 C17 -179.8(3) . . . . ?
N14 C13A N18 N11 179.4(3) . . . . ?
N13 C13A N18 N11 -0.6(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
C2 H2A N11 0.93 2.55 3.389(4) 150.2 2_655
C6 H6A Cl1 0.93 2.89 3.681(4) 144.2 3_655
C151 H15A Cl1 0.96 2.89 3.704(4) 143.2 1_455
C16 H16A Cl1 0.93 2.87 3.632(3) 140.4 1_455
C171 H17A Cl1 0.97 2.86 3.744(3) 152.5 2_645
C171 H17B Cl2 0.97 2.98 3.817(3) 145.6 1_455

_refine_diff_density_max         0.672
_refine_diff_density_min         -0.592
_refine_diff_density_rms         0.086

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_e861a
_database_code_depnum_ccdc_archive 'CCDC 1528388'
_audit_update_record             
;
2017-01-18 deposited with the CCDC.
2017-06-21 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT971_e861a               
;
PROBLEM: Check Calcd Residual Density  0.82A From     Pt1       4.15 eA-3
RESPONSE: The atom type is correct,  there is no missing solvent in the coordination sphere.  The crystal was twinned, so the satellite peaks are the residual density coming from the overlaping reflections
;
# Added during the CSD deposition process: Wednesday 18 January 2017 06:28 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H20 Cl2 N4 O Pt S'
_chemical_formula_sum            'C12 H20 Cl2 N4 O Pt S'
_chemical_formula_weight         534.37

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'
Pt Pt -1.7033 8.3905 '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                   13.0528(4)
_cell_length_b                   10.3031(3)
_cell_length_c                   13.9763(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.763(3)
_cell_angle_gamma                90
_cell_volume                     1852.37(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6742
_cell_measurement_theta_min      1.9696
_cell_measurement_theta_max      28.2638

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.916
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.525
_exptl_crystal_size_mid          0.323
_exptl_crystal_size_min          0.118
_exptl_absorpt_coefficient_mu    7.979
_shelx_estimated_absorpt_T_min   0.102
_shelx_estimated_absorpt_T_max   0.453
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.087
_exptl_absorpt_correction_T_max  0.436
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Oxford Sapphire CCD'
_diffrn_measurement_method       θ/2θ
_diffrn_detector_area_resol_mean 8.2564
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            12537
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.469
_diffrn_reflns_theta_max         28.357
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4229
_reflns_number_gt                3260
_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       'Oxford Diffraction CrysAlis'
_computing_cell_refinement       'Oxford Diffraction CrysAlis'
_computing_data_reduction        'Oxford Diffraction CrysAlis'
_computing_structure_solution    'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_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)+(0.0547P)²] 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         4229
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0927
_refine_ls_wR_factor_gt          0.0897
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
Pt1 Pt 0.60129(2) 0.56905(2) 0.14053(2) 0.03326(9) Uani 1 1 d . . . . .
Cl1 Cl 0.76626(13) 0.55527(17) 0.10360(13) 0.0491(4) Uani 1 1 d . . . . .
Cl2 Cl 0.56024(15) 0.73212(18) 0.02747(13) 0.0569(5) Uani 1 1 d . . . . .
S3 S 0.63002(13) 0.40395(16) 0.24041(13) 0.0439(4) Uani 1 1 d . . . . .
O31 O 0.5426(4) 0.3582(5) 0.2817(4) 0.0637(14) Uani 1 1 d . . . . .
C32 C 0.7335(7) 0.4366(7) 0.3381(6) 0.069(2) Uani 1 1 d . . . . .
H32A H 0.7929 0.4673 0.3127 0.083 Uiso 1 1 calc R U . . .
H32B H 0.7119 0.5015 0.3797 0.083 Uiso 1 1 calc R U . . .
H32C H 0.7514 0.3584 0.3746 0.083 Uiso 1 1 calc R U . . .
C33 C 0.6796(8) 0.2718(7) 0.1797(7) 0.077(3) Uani 1 1 d . . . . .
H33A H 0.7379 0.3007 0.1518 0.092 Uiso 1 1 calc R U . . .
H33B H 0.7013 0.2035 0.2254 0.092 Uiso 1 1 calc R U . . .
H33C H 0.6263 0.2400 0.1293 0.092 Uiso 1 1 calc R U . . .
N1 N 0.2859(4) 0.5778(6) 0.1634(4) 0.0527(15) Uani 1 1 d . . . . .
C2 C 0.3661(5) 0.5579(7) 0.1225(5) 0.0496(17) Uani 1 1 d . . . . .
H2A H 0.3603 0.5232 0.0604 0.060 Uiso 1 1 calc R U . . .
N3 N 0.4582(4) 0.5902(5) 0.1750(4) 0.0372(12) Uani 1 1 d . . . . .
C3A C 0.4356(5) 0.6375(6) 0.2584(4) 0.0381(13) Uani 1 1 d . . . . .
N4 N 0.5002(5) 0.6837(6) 0.3350(4) 0.0522(15) Uani 1 1 d . . . . .
C5 C 0.4532(6) 0.7286(8) 0.4052(5) 0.062(2) Uani 1 1 d . . . . .
C51 C 0.5242(8) 0.7792(11) 0.4938(6) 0.106(4) Uani 1 1 d . . . . .
H51A H 0.4834 0.8094 0.5403 0.127 Uiso 1 1 calc R U . . .
H51B H 0.5695 0.7109 0.5220 0.127 Uiso 1 1 calc R U . . .
H51C H 0.5650 0.8497 0.4754 0.127 Uiso 1 1 calc R U . . .
C6 C 0.3453(6) 0.7232(7) 0.4016(5) 0.062(2) Uani 1 1 d . . . . .
H6A H 0.3172 0.7546 0.4539 0.074 Uiso 1 1 calc R U . . .
C7 C 0.2799(6) 0.6728(6) 0.3230(5) 0.0482(16) Uani 1 1 d . . . . .
C71 C 0.1651(6) 0.6536(7) 0.3108(6) 0.060(2) Uani 1 1 d . . . . .
H71A H 0.1332 0.6896 0.2488 0.072 Uiso 1 1 calc R U . . .
H71B H 0.1389 0.7016 0.3612 0.072 Uiso 1 1 calc R U . . .
C72 C 0.1321(6) 0.5116(8) 0.3153(6) 0.062(2) Uani 1 1 d . . . . .
H72A H 0.1575 0.4646 0.2630 0.074 Uiso 1 1 calc R U . . .
C73 C 0.1777(9) 0.4478(8) 0.4106(9) 0.096(4) Uani 1 1 d . . . . .
H73A H 0.2521 0.4556 0.4209 0.116 Uiso 1 1 calc R U . . .
H73B H 0.1513 0.4898 0.4627 0.116 Uiso 1 1 calc R U . . .
H73C H 0.1588 0.3577 0.4086 0.116 Uiso 1 1 calc R U . . .
C74 C 0.0156(6) 0.4991(10) 0.2996(7) 0.084(3) Uani 1 1 d . . . . .
H74A H -0.0137 0.5395 0.2392 0.101 Uiso 1 1 calc R U . . .
H74B H -0.0032 0.4090 0.2977 0.101 Uiso 1 1 calc R U . . .
H74C H -0.0107 0.5410 0.3518 0.101 Uiso 1 1 calc R U . . .
N8 N 0.3308(4) 0.6304(5) 0.2511(4) 0.0425(12) 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
Pt1 N3 2.018(5) . ?
Pt1 S3 2.1921(16) . ?
Pt1 Cl1 2.3022(16) . ?
Pt1 Cl2 2.3063(17) . ?
S3 O31 1.442(5) . ?
S3 C32 1.782(7) . ?
S3 C33 1.783(8) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
N1 C2 1.291(9) . ?
N1 N8 1.378(7) . ?
C2 N3 1.340(8) . ?
C2 H2A 0.9300 . ?
N3 C3A 1.342(7) . ?
C3A N4 1.333(8) . ?
C3A N8 1.356(7) . ?
N4 C5 1.326(9) . ?
C5 C6 1.401(10) . ?
C5 C51 1.508(11) . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
C6 C7 1.374(10) . ?
C6 H6A 0.9300 . ?
C7 N8 1.366(8) . ?
C7 C71 1.492(10) . ?
C71 C72 1.529(11) . ?
C71 H71A 0.9700 . ?
C71 H71B 0.9700 . ?
C72 C74 1.505(10) . ?
C72 C73 1.513(12) . ?
C72 H72A 0.9800 . ?
C73 H73A 0.9600 . ?
C73 H73B 0.9600 . ?
C73 H73C 0.9600 . ?
C74 H74A 0.9600 . ?
C74 H74B 0.9600 . ?
C74 H74C 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
N3 Pt1 S3 89.84(15) . . ?
N3 Pt1 Cl1 177.19(14) . . ?
S3 Pt1 Cl1 91.68(6) . . ?
N3 Pt1 Cl2 88.16(15) . . ?
S3 Pt1 Cl2 175.09(7) . . ?
Cl1 Pt1 Cl2 90.51(6) . . ?
O31 S3 C32 107.6(4) . . ?
O31 S3 C33 108.5(4) . . ?
C32 S3 C33 102.7(5) . . ?
O31 S3 Pt1 116.5(2) . . ?
C32 S3 Pt1 111.5(2) . . ?
C33 S3 Pt1 109.0(3) . . ?
S3 C32 H32A 109.5 . . ?
S3 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
S3 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
S3 C33 H33A 109.5 . . ?
S3 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
S3 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C2 N1 N8 101.6(5) . . ?
N1 C2 N3 116.0(6) . . ?
N1 C2 H2A 122.0 . . ?
N3 C2 H2A 122.0 . . ?
C2 N3 C3A 104.8(5) . . ?
C2 N3 Pt1 128.6(4) . . ?
C3A N3 Pt1 126.6(4) . . ?
N4 C3A N3 128.6(6) . . ?
N4 C3A N8 124.9(6) . . ?
N3 C3A N8 106.5(5) . . ?
C5 N4 C3A 114.1(6) . . ?
N4 C5 C6 123.2(7) . . ?
N4 C5 C51 115.5(7) . . ?
C6 C5 C51 121.2(7) . . ?
C5 C51 H51A 109.5 . . ?
C5 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C5 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C7 C6 C5 121.9(6) . . ?
C7 C6 H6A 119.1 . . ?
C5 C6 H6A 119.1 . . ?
N8 C7 C6 113.3(6) . . ?
N8 C7 C71 118.5(6) . . ?
C6 C7 C71 128.1(6) . . ?
C7 C71 C72 114.0(6) . . ?
C7 C71 H71A 108.8 . . ?
C72 C71 H71A 108.8 . . ?
C7 C71 H71B 108.8 . . ?
C72 C71 H71B 108.8 . . ?
H71A C71 H71B 107.6 . . ?
C74 C72 C73 109.2(8) . . ?
C74 C72 C71 111.1(7) . . ?
C73 C72 C71 112.3(7) . . ?
C74 C72 H72A 108.0 . . ?
C73 C72 H72A 108.0 . . ?
C71 C72 H72A 108.0 . . ?
C72 C73 H73A 109.5 . . ?
C72 C73 H73B 109.5 . . ?
H73A C73 H73B 109.5 . . ?
C72 C73 H73C 109.5 . . ?
H73A C73 H73C 109.5 . . ?
H73B C73 H73C 109.5 . . ?
C72 C74 H74A 109.5 . . ?
C72 C74 H74B 109.5 . . ?
H74A C74 H74B 109.5 . . ?
C72 C74 H74C 109.5 . . ?
H74A C74 H74C 109.5 . . ?
H74B C74 H74C 109.5 . . ?
C3A N8 C7 122.5(6) . . ?
C3A N8 N1 111.1(5) . . ?
C7 N8 N1 126.4(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N8 N1 C2 N3 0.9(8) . . . . ?
N1 C2 N3 C3A -0.7(8) . . . . ?
N1 C2 N3 Pt1 177.6(5) . . . . ?
C2 N3 C3A N4 -179.7(7) . . . . ?
Pt1 N3 C3A N4 2.0(10) . . . . ?
C2 N3 C3A N8 0.2(7) . . . . ?
Pt1 N3 C3A N8 -178.2(4) . . . . ?
N3 C3A N4 C5 177.4(7) . . . . ?
N8 C3A N4 C5 -2.5(10) . . . . ?
C3A N4 C5 C6 2.6(11) . . . . ?
C3A N4 C5 C51 178.9(7) . . . . ?
N4 C5 C6 C7 -1.4(13) . . . . ?
C51 C5 C6 C7 -177.5(8) . . . . ?
C5 C6 C7 N8 -0.2(11) . . . . ?
C5 C6 C7 C71 176.2(7) . . . . ?
N8 C7 C71 C72 68.5(9) . . . . ?
C6 C7 C71 C72 -107.7(9) . . . . ?
C7 C71 C72 C74 -178.3(7) . . . . ?
C7 C71 C72 C73 59.0(9) . . . . ?
N4 C3A N8 C7 1.1(10) . . . . ?
N3 C3A N8 C7 -178.8(6) . . . . ?
N4 C3A N8 N1 -179.8(6) . . . . ?
N3 C3A N8 N1 0.4(7) . . . . ?
C6 C7 N8 C3A 0.3(10) . . . . ?
C71 C7 N8 C3A -176.4(6) . . . . ?
C6 C7 N8 N1 -178.7(7) . . . . ?
C71 C7 N8 N1 4.6(10) . . . . ?
C2 N1 N8 C3A -0.7(7) . . . . ?
C2 N1 N8 C7 178.4(7) . . . . ?

_refine_diff_density_max         4.609
_refine_diff_density_min         -1.381
_refine_diff_density_rms         0.148

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_e1037a
_database_code_depnum_ccdc_archive 'CCDC 1528389'
_audit_update_record             
;
2017-01-18 deposited with the CCDC.
2017-06-21 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT213_e1037a              
;
PROBLEM: Atom C3A             has ADP max/min Ratio .....        5.1 prolat
RESPONSE: Thin crystal and twinning resulted in the ADP fit to the experiment.
;
_vrf_PLAT971_e1037a              
;
PROBLEM: Check Calcd Residual Density  1.01A From     Pt1       7.27 eA-3
RESPONSE: The coordination sphere is correct. Thin crystal and twinning resulted in the residual density peak near Pt..
;
# Added during the CSD deposition process: Wednesday 18 January 2017 06:28 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H17 Cl2 N5 Pt'
_chemical_formula_sum            'C10 H17 Cl2 N5 Pt'
_chemical_formula_weight         473.27

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pt Pt -1.7033 8.3905 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   13.983(4)
_cell_length_b                   7.6739(11)
_cell_length_c                   15.073(4)
_cell_angle_alpha                90
_cell_angle_beta                 116.36(4)
_cell_angle_gamma                90
_cell_volume                     1449.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3063
_cell_measurement_theta_min      2.6512
_cell_measurement_theta_max      28.6598

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.169
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.026
_exptl_absorpt_coefficient_mu    10.041
_shelx_estimated_absorpt_T_min   0.152
_shelx_estimated_absorpt_T_max   0.780
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.1496
_exptl_absorpt_correction_T_max  0.7132
_exptl_absorpt_process_details   'Rigaku OD CrysAlis Pro'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Oxford Sapphire CCD'
_diffrn_measurement_method       θ/2θ
_diffrn_detector_area_resol_mean 8.2564
_diffrn_reflns_number            8426
_diffrn_reflns_av_unetI/netI     0.1086
_diffrn_reflns_av_R_equivalents  0.1059
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.718
_diffrn_reflns_theta_max         28.424
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.905
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3303
_reflns_number_gt                2171
_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       'Rigaku OD CrysAlisPro 1.171.38.43'
_computing_cell_refinement       'Rigaku OD CrysAlisPro 1.171.38.43'
_computing_data_reduction        'Rigaku OD CrysAlisPro 1.171.38.43'
_computing_structure_solution    'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'CIFTAB (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)+(0.1248P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     patterson
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3303
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1176
_refine_ls_R_factor_gt           0.0766
_refine_ls_wR_factor_ref         0.2130
_refine_ls_wR_factor_gt          0.1946
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
Pt1 Pt 0.43781(5) 0.08663(8) 0.81228(5) 0.0282(2) Uani 1 1 d . . . . .
Cl1 Cl 0.3393(4) 0.1178(5) 0.8996(3) 0.0386(11) Uani 1 1 d . . . . .
Cl2 Cl 0.3022(4) -0.0527(6) 0.6813(4) 0.0412(10) Uani 1 1 d . . . . .
N21 N 0.5635(12) 0.2009(19) 0.9282(11) 0.037(4) Uani 1 1 d . . . . .
H1N H 0.5448 0.2255 0.9761 0.02(4) Uiso 1 1 calc R . . . .
H2N H 0.6188 0.1282 0.9513 0.13(13) Uiso 1 1 calc R . . . .
H3N H 0.5815 0.2988 0.9077 0.198 Uiso 1 1 calc R U . . .
N1 N 0.5845(12) 0.1066(17) 0.6238(11) 0.033(3) Uani 1 1 d . . . . .
C2 C 0.5056(14) 0.132(2) 0.6479(13) 0.032(4) Uani 1 1 d . . . . .
H2A H 0.4413 0.1854 0.6070 0.038 Uiso 1 1 calc R U . . .
N3 N 0.5302(11) 0.0700(15) 0.7401(9) 0.023(3) Uani 1 1 d . . . . .
C3A C 0.6238(15) 0.0061(19) 0.7748(12) 0.029(4) Uani 1 1 d . . . . .
N4 N 0.6851(12) -0.0619(17) 0.8655(10) 0.030(3) Uani 1 1 d . . . . .
C5 C 0.7791(16) -0.113(2) 0.8814(14) 0.039(4) Uani 1 1 d . . . . .
C51 C 0.8474(15) -0.199(3) 0.9760(15) 0.046(5) Uani 1 1 d . . . . .
H51A H 0.9145 -0.2289 0.9770 0.055 Uiso 1 1 calc R U . . .
H51B H 0.8595 -0.1204 1.0297 0.055 Uiso 1 1 calc R U . . .
H51C H 0.8128 -0.3021 0.9829 0.055 Uiso 1 1 calc R U . . .
C6 C 0.8206(14) -0.090(2) 0.8117(13) 0.032(4) Uani 1 1 d . . . . .
H6A H 0.8901 -0.1254 0.8283 0.039 Uiso 1 1 calc R U . . .
C7 C 0.7604(14) -0.017(2) 0.7198(13) 0.028(3) Uani 1 1 d . . . . .
C71 C 0.7943(17) 0.020(2) 0.6454(13) 0.037(5) Uani 1 1 d . . . . .
H71A H 0.7353 -0.0015 0.5810 0.045 Uiso 1 1 calc R U . . .
H71B H 0.8516 -0.0588 0.6534 0.045 Uiso 1 1 calc R U . . .
C72 C 0.8346(17) 0.215(3) 0.6479(16) 0.051(5) Uani 1 1 d . . . . .
H72A H 0.7728 0.2925 0.6279 0.061 Uiso 1 1 calc R U . . .
C73 C 0.876(2) 0.228(3) 0.5684(17) 0.065(7) Uani 1 1 d . . . . .
H73A H 0.8218 0.1898 0.5057 0.098 Uiso 1 1 calc R U . . .
H73B H 0.8950 0.3465 0.5631 0.098 Uiso 1 1 calc R U . . .
H73C H 0.9383 0.1553 0.5873 0.098 Uiso 1 1 calc R U . . .
C74 C 0.9139(19) 0.271(3) 0.7443(19) 0.067(7) Uani 1 1 d . . . . .
H74A H 0.8853 0.2613 0.7914 0.101 Uiso 1 1 calc R U . . .
H74B H 0.9762 0.1989 0.7648 0.101 Uiso 1 1 calc R U . . .
H74C H 0.9329 0.3901 0.7407 0.101 Uiso 1 1 calc R U . . .
N8 N 0.6625(12) 0.0327(16) 0.7069(10) 0.027(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
Pt1 N3 2.029(13) . ?
Pt1 N21 2.046(15) . ?
Pt1 Cl1 2.301(4) . ?
Pt1 Cl2 2.305(5) . ?
N21 H1N 0.8900 . ?
N21 H2N 0.8900 . ?
N21 H3N 0.8900 . ?
N1 C2 1.32(2) . ?
N1 N8 1.37(2) . ?
C2 N3 1.36(2) . ?
C2 H2A 0.9300 . ?
N3 C3A 1.27(2) . ?
C3A N4 1.35(2) . ?
C3A N8 1.368(19) . ?
N4 C5 1.29(2) . ?
C5 C6 1.42(3) . ?
C5 C51 1.47(2) . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
C6 C7 1.38(2) . ?
C6 H6A 0.9300 . ?
C7 N8 1.35(2) . ?
C7 C71 1.43(2) . ?
C71 C72 1.59(2) . ?
C71 H71A 0.9700 . ?
C71 H71B 0.9700 . ?
C72 C74 1.45(3) . ?
C72 C73 1.55(3) . ?
C72 H72A 0.9800 . ?
C73 H73A 0.9600 . ?
C73 H73B 0.9600 . ?
C73 H73C 0.9600 . ?
C74 H74A 0.9600 . ?
C74 H74B 0.9600 . ?
C74 H74C 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
N3 Pt1 N21 88.6(5) . . ?
N3 Pt1 Cl1 176.8(4) . . ?
N21 Pt1 Cl1 88.4(4) . . ?
N3 Pt1 Cl2 89.4(4) . . ?
N21 Pt1 Cl2 177.1(4) . . ?
Cl1 Pt1 Cl2 93.67(18) . . ?
Pt1 N21 H1N 109.5 . . ?
Pt1 N21 H2N 109.5 . . ?
H1N N21 H2N 109.5 . . ?
Pt1 N21 H3N 109.5 . . ?
H1N N21 H3N 109.5 . . ?
H2N N21 H3N 109.5 . . ?
C2 N1 N8 103.4(13) . . ?
N1 C2 N3 111.5(15) . . ?
N1 C2 H2A 124.2 . . ?
N3 C2 H2A 124.2 . . ?
C3A N3 C2 107.5(13) . . ?
C3A N3 Pt1 126.0(10) . . ?
C2 N3 Pt1 126.4(11) . . ?
N3 C3A N4 129.5(14) . . ?
N3 C3A N8 108.2(14) . . ?
N4 C3A N8 122.0(17) . . ?
C5 N4 C3A 116.1(15) . . ?
N4 C5 C6 122.9(16) . . ?
N4 C5 C51 119.1(17) . . ?
C6 C5 C51 118.0(18) . . ?
C5 C51 H51A 109.5 . . ?
C5 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C5 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C7 C6 C5 121.7(17) . . ?
C7 C6 H6A 119.1 . . ?
C5 C6 H6A 119.1 . . ?
N8 C7 C6 112.8(14) . . ?
N8 C7 C71 120.0(16) . . ?
C6 C7 C71 127.1(17) . . ?
C7 C71 C72 114.0(14) . . ?
C7 C71 H71A 108.7 . . ?
C72 C71 H71A 108.7 . . ?
C7 C71 H71B 108.7 . . ?
C72 C71 H71B 108.7 . . ?
H71A C71 H71B 107.6 . . ?
C74 C72 C73 111.9(19) . . ?
C74 C72 C71 114.1(18) . . ?
C73 C72 C71 107.0(17) . . ?
C74 C72 H72A 107.9 . . ?
C73 C72 H72A 107.9 . . ?
C71 C72 H72A 107.9 . . ?
C72 C73 H73A 109.5 . . ?
C72 C73 H73B 109.5 . . ?
H73A C73 H73B 109.5 . . ?
C72 C73 H73C 109.5 . . ?
H73A C73 H73C 109.5 . . ?
H73B C73 H73C 109.5 . . ?
C72 C74 H74A 109.5 . . ?
C72 C74 H74B 109.5 . . ?
H74A C74 H74B 109.5 . . ?
C72 C74 H74C 109.5 . . ?
H74A C74 H74C 109.5 . . ?
H74B C74 H74C 109.5 . . ?
C7 N8 N1 126.5(13) . . ?
C7 N8 C3A 124.2(15) . . ?
N1 N8 C3A 109.2(14) . . ?

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
N8 N1 C2 N3 -2.7(17) . . . . ?
N1 C2 N3 C3A 0.1(19) . . . . ?
N1 C2 N3 Pt1 177.4(10) . . . . ?
C2 N3 C3A N4 176.0(16) . . . . ?
Pt1 N3 C3A N4 -1(2) . . . . ?
C2 N3 C3A N8 2.5(17) . . . . ?
Pt1 N3 C3A N8 -174.8(9) . . . . ?
N3 C3A N4 C5 -178.0(17) . . . . ?
N8 C3A N4 C5 -5(2) . . . . ?
C3A N4 C5 C6 4(2) . . . . ?
C3A N4 C5 C51 -176.1(16) . . . . ?
N4 C5 C6 C7 -3(3) . . . . ?
C51 C5 C6 C7 177.6(16) . . . . ?
C5 C6 C7 N8 2(2) . . . . ?
C5 C6 C7 C71 176.8(15) . . . . ?
N8 C7 C71 C72 80(2) . . . . ?
C6 C7 C71 C72 -95(2) . . . . ?
C7 C71 C72 C74 51(3) . . . . ?
C7 C71 C72 C73 175.5(18) . . . . ?
C6 C7 N8 N1 -179.0(14) . . . . ?
C71 C7 N8 N1 6(2) . . . . ?
C6 C7 N8 C3A -3(2) . . . . ?
C71 C7 N8 C3A -178.5(14) . . . . ?
C2 N1 N8 C7 -179.5(15) . . . . ?
C2 N1 N8 C3A 4.1(16) . . . . ?
N3 C3A N8 C7 179.2(13) . . . . ?
N4 C3A N8 C7 5(2) . . . . ?
N3 C3A N8 N1 -4.3(17) . . . . ?
N4 C3A N8 N1 -178.3(14) . . . . ?

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
N21 H1N N1 0.89 2.41 3.191(19) 146.2 4_566
N21 H2N Cl1 0.89 2.79 3.381(17) 125.0 3_657
N21 H2N N4 0.89 2.39 3.05(2) 130.5 .
N21 H3N Cl2 0.89 2.77 3.548(15) 146.4 2_656
C51 H51C Cl2 0.96 2.98 3.60(2) 123.8 2_646

_refine_diff_density_max         6.811
_refine_diff_density_min         -2.450
_refine_diff_density_rms         0.404

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_e997a
_database_code_depnum_ccdc_archive 'CCDC 1528386'
_audit_update_record             
;
2017-01-18 deposited with the CCDC.
2017-06-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H14 N4'
_chemical_formula_sum            'C10 H14 N4'
_chemical_formula_weight         190.25

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   11.469(4)
_cell_length_b                   9.5060(10)
_cell_length_c                   19.520(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2128.1(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    311
_cell_measurement_theta_min      2.0570
_cell_measurement_theta_max      28.3746

_exptl_crystal_description       Needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.712
_exptl_crystal_size_mid          0.241
_exptl_crystal_size_min          0.187
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.9634
_exptl_absorpt_correction_T_max  0.9879
_exptl_absorpt_process_details   'Rigaku OD CrysAlis Pro'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Oxford Sapphire CCD'
_diffrn_measurement_method       θ/2θ
_diffrn_detector_area_resol_mean 8.2564
_diffrn_reflns_number            13683
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.740
_diffrn_reflns_theta_max         28.444
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2504
_reflns_number_gt                1601
_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       'Rigaku OD CrysAlisPro 1.171.38.43'
_computing_cell_refinement       'Rigaku OD CrysAlisPro 1.171.38.43'
_computing_data_reduction        'Rigaku OD CrysAlisPro 1.171.38.43'
_computing_structure_solution    'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'CIFTAB (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)+(0.1266P)²+0.7140P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2504
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1066
_refine_ls_R_factor_gt           0.0708
_refine_ls_wR_factor_ref         0.2330
_refine_ls_wR_factor_gt          0.2051
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
N1 N 0.6171(2) -0.0366(2) 0.37737(11) 0.0608(6) Uani 1 1 d . . . . .
C2 C 0.7218(2) -0.0684(3) 0.40163(16) 0.0676(7) Uani 1 1 d . . . . .
H2A H 0.7681 -0.1360 0.3805 0.081 Uiso 1 1 calc R U . . .
N3 N 0.75896(18) 0.0005(2) 0.45795(13) 0.0645(6) Uani 1 1 d . . . . .
C3A C 0.66959(18) 0.0856(2) 0.47137(12) 0.0485(6) Uani 1 1 d . . . . .
N4 N 0.65882(17) 0.1778(2) 0.52284(10) 0.0521(5) Uani 1 1 d . . . . .
C5 C 0.5602(2) 0.2504(3) 0.52476(12) 0.0501(6) Uani 1 1 d . . . . .
C51 C 0.5463(3) 0.3546(3) 0.58103(15) 0.0718(8) Uani 1 1 d . . . . .
H51A H 0.4719 0.4000 0.5769 0.086 Uiso 1 1 calc R U . . .
H51B H 0.5509 0.3073 0.6244 0.086 Uiso 1 1 calc R U . . .
H51C H 0.6071 0.4237 0.5781 0.086 Uiso 1 1 calc R U . . .
C6 C 0.46984(19) 0.2320(3) 0.47604(12) 0.0503(6) Uani 1 1 d . . . . .
H6A H 0.4020 0.2851 0.4798 0.060 Uiso 1 1 calc R U . . .
C7 C 0.48061(18) 0.1381(2) 0.42399(11) 0.0469(6) Uani 1 1 d . . . . .
C71 C 0.3916(2) 0.1097(3) 0.36983(12) 0.0585(7) Uani 1 1 d . . . . .
H71A H 0.3165 0.1425 0.3862 0.070 Uiso 1 1 calc R U . . .
H71B H 0.3859 0.0088 0.3634 0.070 Uiso 1 1 calc R U . . .
C72 C 0.4154(3) 0.1767(4) 0.30159(16) 0.0903(11) Uani 1 1 d . . . . .
H72A H 0.4841 0.1280 0.2834 0.108 Uiso 1 1 calc R U . . .
C73 C 0.3166(4) 0.1423(5) 0.25209(18) 0.1244(17) Uani 1 1 d . . . . .
H73A H 0.2994 0.0436 0.2543 0.149 Uiso 1 1 calc R U . . .
H73B H 0.2485 0.1952 0.2645 0.149 Uiso 1 1 calc R U . . .
H73C H 0.3397 0.1666 0.2063 0.149 Uiso 1 1 calc R U . . .
C74 C 0.4439(5) 0.3221(5) 0.3001(2) 0.143(2) Uani 1 1 d . . . . .
H74A H 0.4569 0.3510 0.2536 0.171 Uiso 1 1 calc R U . . .
H74B H 0.3808 0.3756 0.3192 0.171 Uiso 1 1 calc R U . . .
H74C H 0.5133 0.3381 0.3264 0.171 Uiso 1 1 calc R U . . .
N8 N 0.58358(15) 0.06524(19) 0.42277(9) 0.0464(5) 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
N1 C2 1.326(4) . ?
N1 N8 1.368(3) . ?
C2 N3 1.349(4) . ?
C2 H2A 0.9300 . ?
N3 C3A 1.331(3) . ?
C3A N4 1.339(3) . ?
C3A N8 1.382(3) . ?
N4 C5 1.325(3) . ?
C5 C6 1.418(3) . ?
C5 C51 1.488(4) . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
C6 C7 1.358(3) . ?
C6 H6A 0.9300 . ?
C7 N8 1.369(3) . ?
C7 C71 1.494(3) . ?
C71 C72 1.501(4) . ?
C71 H71A 0.9700 . ?
C71 H71B 0.9700 . ?
C72 C74 1.421(5) . ?
C72 C73 1.524(4) . ?
C72 H72A 0.9800 . ?
C73 H73A 0.9600 . ?
C73 H73B 0.9600 . ?
C73 H73C 0.9600 . ?
C74 H74A 0.9600 . ?
C74 H74B 0.9600 . ?
C74 H74C 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 N1 N8 100.6(2) . . ?
N1 C2 N3 117.8(2) . . ?
N1 C2 H2A 121.1 . . ?
N3 C2 H2A 121.1 . . ?
C3A N3 C2 102.3(2) . . ?
N3 C3A N4 128.0(2) . . ?
N3 C3A N8 109.2(2) . . ?
N4 C3A N8 122.7(2) . . ?
C5 N4 C3A 116.2(2) . . ?
N4 C5 C6 122.7(2) . . ?
N4 C5 C51 117.3(2) . . ?
C6 C5 C51 119.9(2) . . ?
C5 C51 H51A 109.5 . . ?
C5 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C5 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C7 C6 C5 121.1(2) . . ?
C7 C6 H6A 119.4 . . ?
C5 C6 H6A 119.4 . . ?
C6 C7 N8 115.1(2) . . ?
C6 C7 C71 125.9(2) . . ?
N8 C7 C71 119.1(2) . . ?
C7 C71 C72 115.3(2) . . ?
C7 C71 H71A 108.5 . . ?
C72 C71 H71A 108.5 . . ?
C7 C71 H71B 108.5 . . ?
C72 C71 H71B 108.5 . . ?
H71A C71 H71B 107.5 . . ?
C74 C72 C71 118.2(3) . . ?
C74 C72 C73 111.5(3) . . ?
C71 C72 C73 109.7(3) . . ?
C74 C72 H72A 105.5 . . ?
C71 C72 H72A 105.5 . . ?
C73 C72 H72A 105.5 . . ?
C72 C73 H73A 109.5 . . ?
C72 C73 H73B 109.5 . . ?
H73A C73 H73B 109.5 . . ?
C72 C73 H73C 109.5 . . ?
H73A C73 H73C 109.5 . . ?
H73B C73 H73C 109.5 . . ?
C72 C74 H74A 109.5 . . ?
C72 C74 H74B 109.5 . . ?
H74A C74 H74B 109.5 . . ?
C72 C74 H74C 109.5 . . ?
H74A C74 H74C 109.5 . . ?
H74B C74 H74C 109.5 . . ?
N1 N8 C7 127.70(19) . . ?
N1 N8 C3A 110.07(19) . . ?
C7 N8 C3A 122.21(19) . . ?

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
N8 N1 C2 N3 0.7(3) . . . . ?
N1 C2 N3 C3A -0.2(3) . . . . ?
C2 N3 C3A N4 179.3(2) . . . . ?
C2 N3 C3A N8 -0.4(3) . . . . ?
N3 C3A N4 C5 180.0(2) . . . . ?
N8 C3A N4 C5 -0.3(3) . . . . ?
C3A N4 C5 C6 0.6(3) . . . . ?
C3A N4 C5 C51 -179.5(2) . . . . ?
N4 C5 C6 C7 -0.4(3) . . . . ?
C51 C5 C6 C7 179.7(2) . . . . ?
C5 C6 C7 N8 -0.1(3) . . . . ?
C5 C6 C7 C71 -180.0(2) . . . . ?
C6 C7 C71 C72 101.9(3) . . . . ?
N8 C7 C71 C72 -77.9(3) . . . . ?
C7 C71 C72 C74 -49.3(5) . . . . ?
C7 C71 C72 C73 -178.5(3) . . . . ?
C2 N1 N8 C7 -179.4(2) . . . . ?
C2 N1 N8 C3A -0.9(2) . . . . ?
C6 C7 N8 N1 178.8(2) . . . . ?
C71 C7 N8 N1 -1.3(3) . . . . ?
C6 C7 N8 C3A 0.4(3) . . . . ?
C71 C7 N8 C3A -179.69(19) . . . . ?
N3 C3A N8 N1 0.9(2) . . . . ?
N4 C3A N8 N1 -178.85(19) . . . . ?
N3 C3A N8 C7 179.51(19) . . . . ?
N4 C3A N8 C7 -0.2(3) . . . . ?

_refine_diff_density_max         0.730
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.053

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
