# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_D17078_sq
_database_code_depnum_ccdc_archive 'CCDC 1956840'
loop_
_audit_author_name
_audit_author_address
'Jonathan Becker'
;Justus Liebig University Giessen
Germany
;
_audit_update_record             
;
2019-11-21 deposited with the CCDC.	2020-08-28 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT974_D17078_sq           
;
PROBLEM: Check Calcd Negative Resid. Density on       Pt1      -2.38 eA-3  
RESPONSE: Caused by absorption effects. Absorption correction could only
          partially compensate these problems.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H22 Cl2 N2 Pt'
_chemical_formula_weight         484.32

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      hexagonal
_space_group_IT_number           177
_space_group_name_H-M_alt        'P 6 2 2'
_space_group_name_Hall           'P 6 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'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, z'
'y, -x+y, z'
'x-y, x, z'
'y, x, -z'
'x-y, -y, -z'
'-x, -x+y, -z'
'-y, -x, -z'
'-x+y, y, -z'
'x, x-y, -z'

_cell_length_a                   24.8348(11)
_cell_length_b                   24.8348(11)
_cell_length_c                   12.1765(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     6503.9(6)
_cell_formula_units_Z            12
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9150
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      31.07

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_F_000             2784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.422
_exptl_crystal_size_mid          0.418
_exptl_crystal_size_min          0.416
_exptl_absorpt_coefficient_mu    6.710
_shelx_estimated_absorpt_T_min   0.164
_shelx_estimated_absorpt_T_max   0.167
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.0017
_exptl_absorpt_correction_T_max  0.0142
_exptl_absorpt_process_details   'SADABS 2016/2(Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'I\mS micro-focus sealed tube, multilayer optics'
_diffrn_measurement_device_type  'Bruker PHOTON100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            580785
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_av_R_equivalents  0.1440
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.343
_diffrn_reflns_theta_max         27.874
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5199
_reflns_number_gt                4643
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 Structure factors included contributions from the .fab file. 
  
 _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       'APEX3 v2019.1-0 (Bruker-AXS, 2017)'
_computing_cell_refinement       'SAINT 8.40A (Bruker-AXS, 2017)'
_computing_data_reduction        'SAINT 8.40A (Bruker-AXS, 2017)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
'Bruker D8 Venture Dual I\mS fixed chi instrument.,SQUEEZE'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0362P)²+5.7170P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined by classical fit to all intensities. 
;
_refine_ls_abs_structure_Flack   0.024(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5199
_refine_ls_number_parameters     184
_refine_ls_number_restraints     125
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0639
_refine_ls_wR_factor_gt          0.0618
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.038
_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 0.40904(2) 0.41292(2) 0.25010(2) 0.02037(7) Uani 1 1 d . . . . .
Cl1 Cl 0.35045(7) 0.43345(8) 0.37184(11) 0.0309(3) Uani 1 1 d . . . . .
Cl2 Cl 0.40062(7) 0.47265(6) 0.11409(10) 0.0254(3) Uani 1 1 d . . . . .
N1 N 0.4625(2) 0.3917(2) 0.1536(4) 0.0233(10) Uani 1 1 d D U . . .
H1A H 0.455(3) 0.391(3) 0.082(2) 0.028 Uiso 1 1 d D U . . .
H1B H 0.4983(18) 0.4273(18) 0.152(5) 0.028 Uiso 1 1 d D U . . .
N2 N 0.4155(2) 0.3549(2) 0.3590(4) 0.0273(11) Uani 1 1 d D U . . .
H2A H 0.422(3) 0.363(3) 0.429(2) 0.033 Uiso 1 1 d D U . . .
H2B H 0.3762(15) 0.325(2) 0.364(5) 0.033 Uiso 1 1 d D U . . .
C1 C 0.4640(3) 0.3387(3) 0.3225(4) 0.0232(13) Uani 1 1 d . U . . .
C2 C 0.4593(3) 0.3334(3) 0.1973(5) 0.0251(13) Uani 1 1 d . U . . .
C3 C 0.5123(3) 0.3225(3) 0.1533(5) 0.0314(13) Uani 1 1 d . U . . .
H3 H 0.510013 0.319188 0.071424 0.038 Uiso 1 1 calc R U . . .
C4 C 0.5022(3) 0.2610(3) 0.2035(5) 0.0326(15) Uani 1 1 d . U . . .
H4 H 0.536021 0.253590 0.176625 0.039 Uiso 1 1 calc R U . . .
C5 C 0.5072(3) 0.2677(3) 0.3299(5) 0.0283(14) Uani 1 1 d . U . . .
H5 H 0.501717 0.228346 0.362616 0.034 Uiso 1 1 calc R U . . .
C6 C 0.4546(3) 0.2781(3) 0.3698(4) 0.0249(11) Uani 1 1 d . U . . .
H6 H 0.456792 0.281650 0.451730 0.030 Uiso 1 1 calc R U . . .
C7 C 0.5280(3) 0.3930(3) 0.3555(5) 0.0308(13) Uani 1 1 d . U . . .
H7A H 0.533270 0.432280 0.324815 0.037 Uiso 1 1 calc R U . . .
H7AB H 0.530595 0.396898 0.436536 0.037 Uiso 1 1 calc R U . . .
C8 C 0.5793(3) 0.3825(3) 0.3135(8) 0.046(2) Uani 1 1 d . U . . .
H8 H 0.620863 0.418034 0.334787 0.055 Uiso 1 1 calc R U . . .
C9 C 0.5747(3) 0.3748(3) 0.1872(6) 0.042(2) Uani 1 1 d . U . . .
H9A H 0.581756 0.413899 0.152815 0.051 Uiso 1 1 calc R U . . .
H9AB H 0.607521 0.366382 0.160702 0.051 Uiso 1 1 calc R U . . .
C10 C 0.5697(3) 0.3214(3) 0.3650(6) 0.0392(15) Uani 1 1 d . U . . .
H10A H 0.603279 0.313660 0.340834 0.047 Uiso 1 1 calc R U . . .
H10B H 0.571267 0.324892 0.446035 0.047 Uiso 1 1 calc R U . . .
C11 C 0.3965(3) 0.2773(3) 0.1625(5) 0.0310(13) Uani 1 1 d . U . . .
H11A H 0.362087 0.283136 0.189005 0.037 Uiso 1 1 calc R U . . .
H11B H 0.394186 0.274524 0.081383 0.037 Uiso 1 1 calc R U . . .
C12 C 0.3894(3) 0.2174(3) 0.2096(5) 0.0331(15) Uani 1 1 d . U . . .
H12 H 0.348310 0.181719 0.186788 0.040 Uiso 1 1 calc R U . . .
C13 C 0.3917(3) 0.2229(3) 0.3383(5) 0.0311(13) Uani 1 1 d . U . . .
H13A H 0.357689 0.229249 0.365058 0.037 Uiso 1 1 calc R U . . .
H13B H 0.386729 0.184258 0.371657 0.037 Uiso 1 1 calc R U . . .
C14 C 0.4406(3) 0.2067(3) 0.1693(5) 0.0395(16) Uani 1 1 d . U . . .
H14A H 0.438715 0.202640 0.088334 0.047 Uiso 1 1 calc R U . . .
H14B H 0.435608 0.167749 0.201144 0.047 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pt1 N2 2.022(5) . ?
Pt1 N1 2.031(4) . ?
Pt1 Cl2 2.3014(12) . ?
Pt1 Cl1 2.3057(13) . ?
N1 C2 1.507(8) . ?
N1 H1A 0.90(2) . ?
N1 H1B 0.89(3) . ?
N2 C1 1.514(8) . ?
N2 H2A 0.87(2) . ?
N2 H2B 0.89(3) . ?
C1 C6 1.517(8) . ?
C1 C2 1.530(7) . ?
C1 C7 1.537(8) . ?
C2 C11 1.543(9) . ?
C2 C3 1.566(8) . ?
C3 C9 1.498(10) . ?
C3 C4 1.546(9) . ?
C3 H3 1.0000 . ?
C4 C14 1.506(10) . ?
C4 C5 1.546(9) . ?
C4 H4 1.0000 . ?
C5 C10 1.515(9) . ?
C5 C6 1.534(8) . ?
C5 H5 1.0000 . ?
C6 C13 1.525(8) . ?
C6 H6 1.0000 . ?
C7 C8 1.513(9) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 C10 1.546(9) . ?
C8 C9 1.548(10) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9AB 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.519(8) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C14 1.506(10) . ?
C12 C13 1.572(9) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Pt1 N1 84.25(19) . . ?
N2 Pt1 Cl2 174.86(14) . . ?
N1 Pt1 Cl2 91.88(13) . . ?
N2 Pt1 Cl1 91.10(14) . . ?
N1 Pt1 Cl1 175.20(13) . . ?
Cl2 Pt1 Cl1 92.83(5) . . ?
C2 N1 Pt1 108.5(3) . . ?
C2 N1 H1A 115(4) . . ?
Pt1 N1 H1A 114(4) . . ?
C2 N1 H1B 121(4) . . ?
Pt1 N1 H1B 102(4) . . ?
H1A N1 H1B 95(5) . . ?
C1 N2 Pt1 110.7(3) . . ?
C1 N2 H2A 106(4) . . ?
Pt1 N2 H2A 123(4) . . ?
C1 N2 H2B 119(4) . . ?
Pt1 N2 H2B 102(4) . . ?
H2A N2 H2B 97(5) . . ?
N2 C1 C6 113.8(5) . . ?
N2 C1 C2 106.2(5) . . ?
C6 C1 C2 109.0(5) . . ?
N2 C1 C7 107.6(5) . . ?
C6 C1 C7 110.4(5) . . ?
C2 C1 C7 109.7(6) . . ?
N1 C2 C1 107.7(5) . . ?
N1 C2 C11 108.4(5) . . ?
C1 C2 C11 110.5(6) . . ?
N1 C2 C3 113.5(5) . . ?
C1 C2 C3 108.8(6) . . ?
C11 C2 C3 107.9(5) . . ?
C9 C3 C4 109.5(5) . . ?
C9 C3 C2 110.6(5) . . ?
C4 C3 C2 107.5(5) . . ?
C9 C3 H3 109.7 . . ?
C4 C3 H3 109.7 . . ?
C2 C3 H3 109.7 . . ?
C14 C4 C3 111.5(6) . . ?
C14 C4 C5 111.3(6) . . ?
C3 C4 C5 108.8(6) . . ?
C14 C4 H4 108.4 . . ?
C3 C4 H4 108.4 . . ?
C5 C4 H4 108.4 . . ?
C10 C5 C6 110.3(5) . . ?
C10 C5 C4 111.6(6) . . ?
C6 C5 C4 107.7(5) . . ?
C10 C5 H5 109.1 . . ?
C6 C5 H5 109.1 . . ?
C4 C5 H5 109.1 . . ?
C1 C6 C13 112.2(5) . . ?
C1 C6 C5 109.0(5) . . ?
C13 C6 C5 110.1(5) . . ?
C1 C6 H6 108.5 . . ?
C13 C6 H6 108.5 . . ?
C5 C6 H6 108.5 . . ?
C8 C7 C1 110.6(5) . . ?
C8 C7 H7A 109.5 . . ?
C1 C7 H7A 109.5 . . ?
C8 C7 H7AB 109.5 . . ?
C1 C7 H7AB 109.5 . . ?
H7A C7 H7AB 108.1 . . ?
C7 C8 C10 107.6(6) . . ?
C7 C8 C9 110.0(6) . . ?
C10 C8 C9 108.4(7) . . ?
C7 C8 H8 110.3 . . ?
C10 C8 H8 110.3 . . ?
C9 C8 H8 110.3 . . ?
C3 C9 C8 111.2(6) . . ?
C3 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
C3 C9 H9AB 109.4 . . ?
C8 C9 H9AB 109.4 . . ?
H9A C9 H9AB 108.0 . . ?
C5 C10 C8 109.7(5) . . ?
C5 C10 H10A 109.7 . . ?
C8 C10 H10A 109.7 . . ?
C5 C10 H10B 109.7 . . ?
C8 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
C12 C11 C2 110.5(5) . . ?
C12 C11 H11A 109.5 . . ?
C2 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C2 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C14 C12 C11 110.8(6) . . ?
C14 C12 C13 110.0(5) . . ?
C11 C12 C13 108.1(5) . . ?
C14 C12 H12 109.3 . . ?
C11 C12 H12 109.3 . . ?
C13 C12 H12 109.3 . . ?
C6 C13 C12 107.8(5) . . ?
C6 C13 H13A 110.1 . . ?
C12 C13 H13A 110.1 . . ?
C6 C13 H13B 110.1 . . ?
C12 C13 H13B 110.1 . . ?
H13A C13 H13B 108.5 . . ?
C12 C14 C4 108.7(5) . . ?
C12 C14 H14A 109.9 . . ?
C4 C14 H14A 109.9 . . ?
C12 C14 H14B 109.9 . . ?
C4 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?

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
_geom_hbond_publ_flag
N1 H1A Cl2 0.90(2) 2.41(3) 3.268(5) 159(5) 7 yes
N1 H1B Cl2 0.89(3) 2.54(3) 3.418(5) 171(5) 4_665 yes
N2 H2A Cl1 0.87(2) 2.48(3) 3.318(5) 160(6) 7_556 yes

_refine_diff_density_max         1.242
_refine_diff_density_min         -3.050
_refine_diff_density_rms         0.118



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DMF, diethyl ether'
####################################################################### 
# 
# 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_D18099
_database_code_depnum_ccdc_archive 'CCDC 1956841'
loop_
_audit_author_name
_audit_author_address
'Jonathan Becker'
;Justus Liebig University Giessen
Germany
;
_audit_update_record             
;
2019-09-30 deposited with the CCDC.	2020-08-28 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT934_D18099              
;
PROBLEM: Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          7 Check 
RESPONSE: Extremly good data set, so outliers appear to have high Error / 
          have high ESDs.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H28 Cl2 N2 O'
_chemical_formula_weight         323.29

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   9.7449(3)
_cell_length_b                   8.4127(3)
_cell_length_c                   9.7717(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.4679(15)
_cell_angle_gamma                90
_cell_volume                     800.35(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9978
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      52.12

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.335
_exptl_crystal_size_min          0.260
_exptl_absorpt_coefficient_mu    0.404
_shelx_estimated_absorpt_T_min   0.805
_shelx_estimated_absorpt_T_max   0.902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6984
_exptl_absorpt_correction_T_max  0.7503
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'I\mS micro-focus sealed tube, multilayer optics'
_diffrn_measurement_device_type  'Bruker PHOTON100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            272934
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.890
_diffrn_reflns_theta_max         49.117
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             16136
_reflns_number_gt                15392
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.921
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    0.999

_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       'APEX3 v2017.3-0 (Bruker-AXS, 2017)'
_computing_cell_refinement       'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_data_reduction        'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker D8 Venture Dual I\mS fixed chi instrument. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0329P)²+0.0050P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 7059 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.004(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         16136
_refine_ls_number_parameters     203
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0207
_refine_ls_R_factor_gt           0.0189
_refine_ls_wR_factor_ref         0.0516
_refine_ls_wR_factor_gt          0.0511
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.002
_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
Cl1 Cl 0.82817(2) 0.06587(2) 0.57900(2) 0.01235(2) Uani 1 1 d . . . . .
Cl2 Cl 0.93029(2) 0.93419(2) 0.06400(2) 0.01266(2) Uani 1 1 d . . . . .
O1 O 0.90671(5) 0.58377(7) 0.68293(4) 0.02008(8) Uani 1 1 d D . . . .
H1 H 0.9565(13) 0.5290(18) 0.7410(14) 0.030 Uiso 1 1 d D U . . .
N1 N 0.88200(4) 0.39407(5) 0.44127(4) 0.00975(5) Uani 1 1 d D . . . .
H1A H 0.8656(11) 0.4632(13) 0.5174(10) 0.012 Uiso 1 1 d D U . . .
H1B H 0.8687(11) 0.2931(13) 0.4710(10) 0.012 Uiso 1 1 d D U . . .
H1C H 0.9617(10) 0.3992(14) 0.4135(10) 0.012 Uiso 1 1 d D U . . .
N2 N 0.93461(3) 0.59506(4) 0.19264(4) 0.00902(4) Uani 1 1 d D . . . .
H2A H 0.9402(11) 0.6877(13) 0.1565(10) 0.011 Uiso 1 1 d D U . . .
H2B H 1.0004(10) 0.5961(14) 0.2592(10) 0.011 Uiso 1 1 d D U . . .
H2C H 0.9530(10) 0.5305(13) 0.1295(10) 0.011 Uiso 1 1 d D U . . .
C1 C 0.77776(4) 0.41397(4) 0.32369(4) 0.00758(5) Uani 1 1 d . . . . .
C2 C 0.79437(4) 0.57527(5) 0.24982(4) 0.00742(4) Uani 1 1 d . . . . .
C3 C 0.68653(4) 0.58051(5) 0.12874(4) 0.01011(5) Uani 1 1 d . . . . .
H3 H 0.697770 0.681815 0.076877 0.012 Uiso 1 1 calc R U . . .
C4 C 0.54224(4) 0.57709(6) 0.18738(4) 0.01166(6) Uani 1 1 d . . . . .
H4 H 0.471953 0.583608 0.109954 0.014 Uiso 1 1 calc R U . . .
C5 C 0.52477(4) 0.41783(5) 0.26298(4) 0.01103(6) Uani 1 1 d . . . . .
H5 H 0.430867 0.413710 0.300271 0.013 Uiso 1 1 calc R U . . .
C6 C 0.63253(4) 0.41076(5) 0.38288(4) 0.00910(5) Uani 1 1 d . . . . .
H6 H 0.620998 0.308907 0.433871 0.011 Uiso 1 1 calc R U . . .
C7 C 0.79463(4) 0.27392(5) 0.22575(5) 0.01062(5) Uani 1 1 d . . . . .
H7A H 0.784964 0.172687 0.276095 0.013 Uiso 1 1 calc R U . . .
H7AB H 0.887443 0.276732 0.188420 0.013 Uiso 1 1 calc R U . . .
C8 C 0.68580(5) 0.28260(6) 0.10811(5) 0.01279(6) Uani 1 1 d . . . . .
H8 H 0.697532 0.191128 0.044314 0.015 Uiso 1 1 calc R U . . .
C9 C 0.70238(4) 0.43940(7) 0.03064(4) 0.01287(6) Uani 1 1 d . . . . .
H9A H 0.632046 0.446361 -0.045300 0.015 Uiso 1 1 calc R U . . .
H9AB H 0.794094 0.443092 -0.009070 0.015 Uiso 1 1 calc R U . . .
C10 C 0.54229(5) 0.27673(6) 0.16628(5) 0.01425(7) Uani 1 1 d . . . . .
H10A H 0.471544 0.281256 0.090571 0.017 Uiso 1 1 calc R U . . .
H10B H 0.530567 0.175903 0.216686 0.017 Uiso 1 1 calc R U . . .
C11 C 0.77340(4) 0.71486(5) 0.34811(4) 0.00985(5) Uani 1 1 d . . . . .
H11A H 0.842882 0.709855 0.424936 0.012 Uiso 1 1 calc R U . . .
H11B H 0.785483 0.816568 0.299110 0.012 Uiso 1 1 calc R U . . .
C12 C 0.62877(4) 0.70772(5) 0.40413(5) 0.01168(6) Uani 1 1 d . . . . .
H12 H 0.615786 0.798658 0.468195 0.014 Uiso 1 1 calc R U . . .
C13 C 0.52250(5) 0.71803(6) 0.28409(5) 0.01428(7) Uani 1 1 d . . . . .
H13A H 0.534062 0.819096 0.233987 0.017 Uiso 1 1 calc R U . . .
H13B H 0.428622 0.715735 0.318954 0.017 Uiso 1 1 calc R U . . .
C14 C 0.60951(4) 0.55023(5) 0.48012(4) 0.01132(6) Uani 1 1 d . . . . .
H14A H 0.675714 0.543861 0.559669 0.014 Uiso 1 1 calc R U . . .
H14B H 0.515522 0.544870 0.514467 0.014 Uiso 1 1 calc R U . . .
C15 C 0.81860(6) 0.68348(7) 0.75794(5) 0.01575(7) Uani 1 1 d . . . . .
H15A H 0.788312 0.773454 0.700538 0.024 Uiso 1 1 calc R U . . .
H15B H 0.868509 0.723120 0.840214 0.024 Uiso 1 1 calc R U . . .
H15C H 0.738394 0.622413 0.784643 0.024 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C15 1.4257(7) . ?
O1 H1 0.864(13) . ?
N1 C1 1.5098(5) . ?
N1 H1A 0.963(10) . ?
N1 H1B 0.908(11) . ?
N1 H1C 0.835(10) . ?
N2 C2 1.5078(5) . ?
N2 H2A 0.858(10) . ?
N2 H2B 0.893(10) . ?
N2 H2C 0.847(10) . ?
C1 C7 1.5312(5) . ?
C1 C2 1.5487(5) . ?
C1 C6 1.5519(5) . ?
C2 C11 1.5363(6) . ?
C2 C3 1.5489(5) . ?
C3 C9 1.5377(7) . ?
C3 C4 1.5413(6) . ?
C3 H3 1.0000 . ?
C4 C13 1.5335(7) . ?
C4 C5 1.5429(6) . ?
C4 H4 1.0000 . ?
C5 C10 1.5313(7) . ?
C5 C6 1.5404(6) . ?
C5 H5 1.0000 . ?
C6 C14 1.5324(6) . ?
C6 H6 1.0000 . ?
C7 C8 1.5319(6) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 C10 1.5328(7) . ?
C8 C9 1.5329(7) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9AB 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.5349(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5334(7) . ?
C12 C14 1.5343(6) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
C15 O1 H1 108.1(9) . . ?
C1 N1 H1A 113.1(6) . . ?
C1 N1 H1B 104.3(6) . . ?
H1A N1 H1B 106.7(9) . . ?
C1 N1 H1C 110.6(7) . . ?
H1A N1 H1C 114.0(10) . . ?
H1B N1 H1C 107.5(10) . . ?
C2 N2 H2A 109.1(7) . . ?
C2 N2 H2B 111.4(7) . . ?
H2A N2 H2B 103.6(10) . . ?
C2 N2 H2C 115.0(7) . . ?
H2A N2 H2C 105.3(10) . . ?
H2B N2 H2C 111.6(10) . . ?
N1 C1 C7 107.66(3) . . ?
N1 C1 C2 111.80(3) . . ?
C7 C1 C2 111.51(3) . . ?
N1 C1 C6 108.00(3) . . ?
C7 C1 C6 110.10(3) . . ?
C2 C1 C6 107.71(3) . . ?
N2 C2 C11 107.12(3) . . ?
N2 C2 C1 112.59(3) . . ?
C11 C2 C1 111.04(3) . . ?
N2 C2 C3 108.04(3) . . ?
C11 C2 C3 110.59(3) . . ?
C1 C2 C3 107.45(3) . . ?
C9 C3 C4 109.58(4) . . ?
C9 C3 C2 111.79(3) . . ?
C4 C3 C2 108.38(3) . . ?
C9 C3 H3 109.0 . . ?
C4 C3 H3 109.0 . . ?
C2 C3 H3 109.0 . . ?
C13 C4 C3 110.82(4) . . ?
C13 C4 C5 110.92(4) . . ?
C3 C4 C5 108.39(3) . . ?
C13 C4 H4 108.9 . . ?
C3 C4 H4 108.9 . . ?
C5 C4 H4 108.9 . . ?
C10 C5 C6 110.42(4) . . ?
C10 C5 C4 111.10(4) . . ?
C6 C5 C4 108.18(3) . . ?
C10 C5 H5 109.0 . . ?
C6 C5 H5 109.0 . . ?
C4 C5 H5 109.0 . . ?
C14 C6 C5 109.20(3) . . ?
C14 C6 C1 112.21(3) . . ?
C5 C6 C1 108.58(3) . . ?
C14 C6 H6 108.9 . . ?
C5 C6 H6 108.9 . . ?
C1 C6 H6 108.9 . . ?
C1 C7 C8 110.05(3) . . ?
C1 C7 H7A 109.7 . . ?
C8 C7 H7A 109.7 . . ?
C1 C7 H7AB 109.7 . . ?
C8 C7 H7AB 109.7 . . ?
H7A C7 H7AB 108.2 . . ?
C7 C8 C10 109.47(4) . . ?
C7 C8 C9 109.11(4) . . ?
C10 C8 C9 109.15(4) . . ?
C7 C8 H8 109.7 . . ?
C10 C8 H8 109.7 . . ?
C9 C8 H8 109.7 . . ?
C8 C9 C3 109.93(3) . . ?
C8 C9 H9A 109.7 . . ?
C3 C9 H9A 109.7 . . ?
C8 C9 H9AB 109.7 . . ?
C3 C9 H9AB 109.7 . . ?
H9A C9 H9AB 108.2 . . ?
C5 C10 C8 109.37(4) . . ?
C5 C10 H10A 109.8 . . ?
C8 C10 H10A 109.8 . . ?
C5 C10 H10B 109.8 . . ?
C8 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
C12 C11 C2 110.00(3) . . ?
C12 C11 H11A 109.7 . . ?
C2 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
C2 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C13 C12 C14 109.05(4) . . ?
C13 C12 C11 108.98(4) . . ?
C14 C12 C11 109.86(3) . . ?
C13 C12 H12 109.6 . . ?
C14 C12 H12 109.6 . . ?
C11 C12 H12 109.6 . . ?
C12 C13 C4 109.22(3) . . ?
C12 C13 H13A 109.8 . . ?
C4 C13 H13A 109.8 . . ?
C12 C13 H13B 109.8 . . ?
C4 C13 H13B 109.8 . . ?
H13A C13 H13B 108.3 . . ?
C6 C14 C12 109.68(3) . . ?
C6 C14 H14A 109.7 . . ?
C12 C14 H14A 109.7 . . ?
C6 C14 H14B 109.7 . . ?
C12 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
_geom_hbond_publ_flag
O1 H1 Cl2 0.864(13) 2.303(13) 3.1438(4) 164.5(13) 2_746 yes
N1 H1A O1 0.963(10) 1.937(10) 2.8517(6) 157.8(9) . yes
N1 H1B Cl1 0.908(11) 2.228(11) 3.1258(4) 169.8(9) . yes
N1 H1C Cl1 0.835(10) 2.480(10) 3.1864(4) 143.0(10) 2_756 yes
N2 H2A Cl2 0.858(10) 2.262(10) 3.1172(4) 173.8(10) . yes
N2 H2B Cl1 0.893(10) 2.265(10) 3.1527(4) 172.7(10) 2_756 yes
N2 H2C Cl2 0.847(10) 2.389(10) 3.1840(4) 156.5(9) 2_745 yes

_refine_diff_density_max         0.265
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.065

