# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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_sadc2c
_database_code_depnum_ccdc_archive 'CCDC 1510881'
_audit_update_record             
;
2016-10-20 deposited with the CCDC.
2017-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H28 Cl4 Cu2 N8 O'
_chemical_formula_weight         725.43

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'
O O 0.0106 0.0060 '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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   15.2959(7)
_cell_length_b                   11.0562(7)
_cell_length_c                   17.2255(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.8680(10)
_cell_angle_gamma                90
_cell_volume                     2909.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    7240
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      30.02

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_F_000             1472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.865
_shelx_estimated_absorpt_T_min   0.707
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7384
_exptl_absorpt_correction_T_max  0.8749
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17107
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.274
_diffrn_reflns_theta_max         30.048
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4272
_reflns_number_gt                3362
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0403P)²+2.9337P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4272
_refine_ls_number_parameters     195
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0847
_refine_ls_wR_factor_gt          0.0776
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.007
_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
Cl1 Cl 0.11879(3) 0.54136(5) 0.13777(3) 0.02331(12) Uani 1 1 d . . . . .
Cu1 Cu 0.20886(2) 0.41172(2) 0.04868(2) 0.01883(8) Uani 1 1 d . . . . .
Cl2 Cl 0.34566(3) 0.45686(5) 0.09001(3) 0.02718(13) Uani 1 1 d . . . . .
N1 N 0.19429(11) 0.52669(16) -0.04173(10) 0.0198(4) Uani 1 1 d . . . . .
C2 C 0.24557(14) 0.6221(2) -0.05921(13) 0.0251(5) Uani 1 1 d . . . . .
H2 H 0.2990 0.6338 -0.0297 0.030 Uiso 1 1 calc R U . . .
C3 C 0.22349(16) 0.7022(2) -0.11771(14) 0.0311(5) Uani 1 1 d . . . . .
H3 H 0.2607 0.7684 -0.1284 0.037 Uiso 1 1 calc R U . . .
C4 C 0.14554(16) 0.6844(2) -0.16096(14) 0.0315(5) Uani 1 1 d . . . . .
H4 H 0.1288 0.7391 -0.2016 0.038 Uiso 1 1 calc R U . . .
C5 C 0.09230(15) 0.5879(2) -0.14539(13) 0.0274(5) Uani 1 1 d . . . . .
H5 H 0.0393 0.5739 -0.1751 0.033 Uiso 1 1 calc R U . . .
C6 C 0.11907(13) 0.51153(19) -0.08430(12) 0.0202(4) Uani 1 1 d . . . . .
N7 N 0.06851(12) 0.41323(16) -0.06512(10) 0.0223(4) Uani 1 1 d . . . . .
H7 H 0.0191 0.3947 -0.0908 0.027 Uiso 1 1 calc R U . . .
N8 N 0.10093(11) 0.34764(16) -0.00370(10) 0.0191(3) Uani 1 1 d . . . . .
C9 C 0.06262(13) 0.25486(18) 0.02412(12) 0.0192(4) Uani 1 1 d . . . . .
C91 C -0.02282(14) 0.2061(2) -0.00728(13) 0.0243(4) Uani 1 1 d . . . . .
H91A H -0.0671 0.2702 -0.0073 0.029 Uiso 1 1 calc R U . . .
H91B H -0.0409 0.1389 0.0254 0.029 Uiso 1 1 calc R U . . .
H91C H -0.0166 0.1773 -0.0605 0.029 Uiso 1 1 calc R U . . .
C10 C 0.11472(13) 0.20008(18) 0.08956(12) 0.0199(4) Uani 1 1 d . . . . .
C11 C 0.08828(16) 0.09863(19) 0.13004(13) 0.0259(5) Uani 1 1 d . . . . .
H11 H 0.0332 0.0618 0.1177 0.031 Uiso 1 1 calc R U . . .
C12 C 0.14417(17) 0.0523(2) 0.18889(14) 0.0306(5) Uani 1 1 d . . . . .
H12 H 0.1275 -0.0166 0.2176 0.037 Uiso 1 1 calc R U . . .
C13 C 0.22396(16) 0.1069(2) 0.20542(13) 0.0287(5) Uani 1 1 d . . . . .
H13 H 0.2635 0.0749 0.2444 0.034 Uiso 1 1 calc R U . . .
C14 C 0.24534(14) 0.2091(2) 0.16421(12) 0.0252(5) Uani 1 1 d . . . . .
H14 H 0.2995 0.2483 0.1767 0.030 Uiso 1 1 calc R U . . .
N15 N 0.19241(11) 0.25480(16) 0.10734(10) 0.0201(4) Uani 1 1 d . . . . .
O1M O 0.0793(3) 0.7832(4) 0.2167(3) 0.0551(12) Uani 0.5 1 d D U P A -1
H1M H 0.093(6) 0.723(5) 0.190(5) 0.11(3) Uiso 0.5 1 d D . P B -1
C1M C 0.0076(10) 0.7675(6) 0.2577(10) 0.046(3) Uani 0.5 1 d D U P A -1
H1M1 H -0.0035 0.8411 0.2874 0.055 Uiso 0.5 1 calc R U P A -1
H1M2 H -0.0429 0.7505 0.2221 0.055 Uiso 0.5 1 calc R U P A -1
H1M3 H 0.0170 0.6994 0.2936 0.055 Uiso 0.5 1 calc R U P A -1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 Cu1 2.5534(6) . ?
Cu1 N8 1.9729(16) . ?
Cu1 N1 2.0139(18) . ?
Cu1 N15 2.0297(18) . ?
Cu1 Cl2 2.2328(6) . ?
N1 C6 1.344(3) . ?
N1 C2 1.357(3) . ?
C2 C3 1.371(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.395(3) . ?
C5 H5 0.9500 . ?
C6 N7 1.383(3) . ?
N7 N8 1.356(2) . ?
N7 H7 0.8800 . ?
N8 C9 1.286(3) . ?
C9 C10 1.477(3) . ?
C9 C91 1.490(3) . ?
C91 H91A 0.9800 . ?
C91 H91B 0.9800 . ?
C91 H91C 0.9800 . ?
C10 N15 1.355(3) . ?
C10 C11 1.391(3) . ?
C11 C12 1.391(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.379(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(3) . ?
C13 H13 0.9500 . ?
C14 N15 1.338(3) . ?
C14 H14 0.9500 . ?
O1M H1M 0.84(2) . ?
O1M C1M 1.345(15) . ?
O1M H1M 0.84(2) . ?
C1M H1M1 0.9800 . ?
C1M H1M2 0.9800 . ?
C1M H1M3 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
N8 Cu1 N1 79.36(7) . . ?
N8 Cu1 N15 78.40(7) . . ?
N1 Cu1 N15 155.90(7) . . ?
N8 Cu1 Cl2 167.30(5) . . ?
N1 Cu1 Cl2 99.86(5) . . ?
N15 Cu1 Cl2 99.78(5) . . ?
N8 Cu1 Cl1 90.69(5) . . ?
N1 Cu1 Cl1 93.92(5) . . ?
N15 Cu1 Cl1 95.54(5) . . ?
Cl2 Cu1 Cl1 102.01(2) . . ?
C6 N1 C2 117.68(18) . . ?
C6 N1 Cu1 113.70(13) . . ?
C2 N1 Cu1 128.26(15) . . ?
N1 C2 C3 122.8(2) . . ?
N1 C2 H2 118.6 . . ?
C3 C2 H2 118.6 . . ?
C2 C3 C4 118.4(2) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C5 C4 C3 120.4(2) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 117.5(2) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 H5 121.2 . . ?
N1 C6 N7 116.19(18) . . ?
N1 C6 C5 123.19(19) . . ?
N7 C6 C5 120.62(19) . . ?
N8 N7 C6 114.81(16) . . ?
N8 N7 H7 122.6 . . ?
C6 N7 H7 122.6 . . ?
C9 N8 N7 124.18(17) . . ?
C9 N8 Cu1 120.17(14) . . ?
N7 N8 Cu1 115.45(13) . . ?
N8 C9 C10 111.89(18) . . ?
N8 C9 C91 124.12(19) . . ?
C10 C9 C91 123.96(18) . . ?
C9 C91 H91A 109.5 . . ?
C9 C91 H91B 109.5 . . ?
H91A C91 H91B 109.5 . . ?
C9 C91 H91C 109.5 . . ?
H91A C91 H91C 109.5 . . ?
H91B C91 H91C 109.5 . . ?
N15 C10 C11 121.36(19) . . ?
N15 C10 C9 115.02(18) . . ?
C11 C10 C9 123.61(19) . . ?
C12 C11 C10 118.6(2) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C13 C12 C11 119.7(2) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 118.8(2) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
N15 C14 C13 122.3(2) . . ?
N15 C14 H14 118.8 . . ?
C13 C14 H14 118.8 . . ?
C14 N15 C10 119.24(19) . . ?
C14 N15 Cu1 126.99(15) . . ?
C10 N15 Cu1 113.47(13) . . ?
H1M O1M C1M 115(6) . . ?
H1M O1M H1M 0(6) . . ?
C1M O1M H1M 115(6) . . ?
O1M C1M H1M1 109.5 . . ?
O1M C1M H1M2 109.5 . . ?
H1M1 C1M H1M2 109.5 . . ?
O1M C1M H1M3 109.5 . . ?
H1M1 C1M H1M3 109.5 . . ?
H1M2 C1M H1M3 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 C3 0.1(3) . . . . ?
Cu1 N1 C2 C3 -172.45(17) . . . . ?
N1 C2 C3 C4 -0.3(4) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 1.1(4) . . . . ?
C2 N1 C6 N7 179.81(19) . . . . ?
Cu1 N1 C6 N7 -6.5(2) . . . . ?
C2 N1 C6 C5 0.7(3) . . . . ?
Cu1 N1 C6 C5 174.35(18) . . . . ?
C4 C5 C6 N1 -1.3(3) . . . . ?
C4 C5 C6 N7 179.6(2) . . . . ?
N1 C6 N7 N8 2.1(3) . . . . ?
C5 C6 N7 N8 -178.7(2) . . . . ?
C6 N7 N8 C9 178.3(2) . . . . ?
C6 N7 N8 Cu1 3.5(2) . . . . ?
N7 N8 C9 C10 178.40(18) . . . . ?
Cu1 N8 C9 C10 -7.0(2) . . . . ?
N7 N8 C9 C91 0.1(3) . . . . ?
Cu1 N8 C9 C91 174.69(16) . . . . ?
N8 C9 C10 N15 -1.0(3) . . . . ?
C91 C9 C10 N15 177.29(19) . . . . ?
N8 C9 C10 C11 -180.0(2) . . . . ?
C91 C9 C10 C11 -1.6(3) . . . . ?
N15 C10 C11 C12 -1.1(3) . . . . ?
C9 C10 C11 C12 177.7(2) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C11 C12 C13 C14 1.8(3) . . . . ?
C12 C13 C14 N15 -2.0(3) . . . . ?
C13 C14 N15 C10 0.5(3) . . . . ?
C13 C14 N15 Cu1 173.82(16) . . . . ?
C11 C10 N15 C14 1.1(3) . . . . ?
C9 C10 N15 C14 -177.89(18) . . . . ?
C11 C10 N15 Cu1 -173.10(16) . . . . ?
C9 C10 N15 Cu1 7.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C14 H14 O1M 0.95 2.57 3.395(6) 145.0 4_545
C14 H14 O1M 0.95 2.57 3.395(6) 145.0 4_545
N7 H7 Cl1 0.88 2.33 3.1093(18) 147.4 5_565
N7 H7 Cl1 0.88 2.33 3.1093(18) 147.4 5_565
C13 H13 Cl1 0.95 2.67 3.600(2) 166.1 4_545
O1M H1M Cl1 0.84(2) 2.24(3) 3.073(4) 168(9) .
C14 H14 O1M 0.95 2.57 3.395(6) 145.0 4_545
C14 H14 O1M 0.95 2.57 3.395(6) 145.0 4_545

_refine_diff_density_max         0.506
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.087

####################################################################### 
# 
# 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_cr170412_0m
_database_code_depnum_ccdc_archive 'CCDC 1510882'
_audit_update_record             
;
2016-10-20 deposited with the CCDC.
2017-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H30 Cl4 Mn2 N8 O3'
_chemical_formula_weight         730.24

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.06430(10)
_cell_length_b                   9.7937(2)
_cell_length_c                   11.6995(2)
_cell_angle_alpha                97.0030(10)
_cell_angle_beta                 101.4300(10)
_cell_angle_gamma                109.0230(10)
_cell_volume                     734.70(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    7866
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      30.09

_exptl_crystal_description       wedge
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_F_000             372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.418
_exptl_crystal_size_mid          0.354
_exptl_crystal_size_min          0.308
_exptl_absorpt_coefficient_mu    1.266
_shelx_estimated_absorpt_T_min   0.620
_shelx_estimated_absorpt_T_max   0.696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6570
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Microfocus
_diffrn_measurement_device_type  'APEX-II CCD-detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12944
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.813
_diffrn_reflns_theta_max         30.093
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4284
_reflns_number_gt                3915
_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       'APEX2 v2012.2-0'
_computing_cell_refinement       'SAINT V8.18C (Bruker AXS Inc.)'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc.)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0323P)²+0.3120P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4284
_refine_ls_number_parameters     234
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0248
_refine_ls_wR_factor_ref         0.0661
_refine_ls_wR_factor_gt          0.0641
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.045
_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
Mn1 Mn 0.26518(3) 0.21385(2) 0.24459(2) 0.01828(6) Uani 1 1 d . . . . .
Cl1A Cl 0.23033(12) -0.01350(11) 0.1124(2) 0.0300(4) Uani 0.563(5) 1 d . . P A
1
Cl1B Cl 0.22235(16) -0.02918(10) 0.1648(3) 0.0304(4) Uani 0.437(5) 1 d . . P A
2
Cl2 Cl 0.66247(5) 0.32818(3) 0.29948(3) 0.02278(7) Uani 1 1 d . . . . .
O1A O 0.9050(6) 0.1231(5) 0.1836(3) 0.0233(6) Uani 0.563(5) 1 d D . P A 1
H1A H 0.842(3) 0.175(2) 0.209(2) 0.029(10) Uiso 0.563(5) 1 d D . P A 1
H1B H 0.863(5) 0.097(4) 0.1092(5) 0.063(13) Uiso 0.563(5) 1 d D . P A 1
O1B O -0.0685(7) 0.1580(5) 0.2212(4) 0.0238(8) Uani 0.437(5) 1 d D . P A 2
H1C H -0.130(3) 0.216(2) 0.235(4) 0.064(19) Uiso 0.437(5) 1 d D . P A 2
H1D H -0.151(4) 0.083(2) 0.171(3) 0.03(2) Uiso 0.437(5) 1 d D . P A 2
N1P N 0.25875(16) 0.17382(12) 0.42874(10) 0.0216(2) Uani 1 1 d . . . . .
C2P C 0.25545(18) 0.28218(14) 0.50842(11) 0.0194(2) Uani 1 1 d . . . . .
C3P C 0.26010(19) 0.27260(15) 0.62726(12) 0.0237(2) Uani 1 1 d . . . . .
H3P H 0.2593 0.3522 0.6821 0.028 Uiso 1 1 calc R U . . .
C4P C 0.2659(2) 0.14428(16) 0.66260(13) 0.0284(3) Uani 1 1 d . . . . .
H4P H 0.2672 0.1339 0.7424 0.034 Uiso 1 1 calc R U . . .
C5P C 0.2696(2) 0.03050(16) 0.58074(14) 0.0297(3) Uani 1 1 d . . . . .
H5P H 0.2746 -0.0584 0.6035 0.036 Uiso 1 1 calc R U . . .
C6P C 0.2661(2) 0.04968(15) 0.46591(13) 0.0255(3) Uani 1 1 d . . . . .
H6P H 0.2689 -0.0281 0.4099 0.031 Uiso 1 1 calc R U . . .
N1R N 0.24552(17) 0.40868(12) 0.46983(9) 0.0202(2) Uani 1 1 d . . . . .
H1R H 0.2344 0.4814 0.5169 0.024 Uiso 1 1 calc R U . . .
N2R N 0.25397(16) 0.41415(11) 0.35548(9) 0.01836(19) Uani 1 1 d . . . . .
C2R C 0.23984(17) 0.52428(12) 0.30935(10) 0.0172(2) Uani 1 1 d . . . . .
C1M C 0.2100(2) 0.65433(13) 0.37286(11) 0.0218(2) Uani 1 1 d . . . . .
H2M H 0.3447 0.7265 0.4188 0.033 Uiso 1 1 calc R U . . .
H1M H 0.1219 0.6224 0.4268 0.033 Uiso 1 1 calc R U . . .
H3M H 0.1437 0.6995 0.3147 0.033 Uiso 1 1 calc R U . . .
N1Q N 0.24365(15) 0.37822(11) 0.12872(9) 0.01848(19) Uani 1 1 d . . . . .
C2Q C 0.24937(17) 0.51018(13) 0.18294(10) 0.0171(2) Uani 1 1 d . . . . .
C3Q C 0.26239(19) 0.62592(14) 0.12325(11) 0.0215(2) Uani 1 1 d . . . . .
H3Q H 0.2706 0.7188 0.1635 0.026 Uiso 1 1 calc R U . . .
C4Q C 0.2632(2) 0.60351(15) 0.00368(12) 0.0250(3) Uani 1 1 d . . . . .
H4Q H 0.2736 0.6813 -0.0387 0.030 Uiso 1 1 calc R U . . .
C5Q C 0.2487(2) 0.46738(16) -0.05229(12) 0.0259(3) Uani 1 1 d . . . . .
H5Q H 0.2443 0.4487 -0.1346 0.031 Uiso 1 1 calc R U . . .
C6Q C 0.24054(19) 0.35748(15) 0.01323(11) 0.0226(2) Uani 1 1 d . . . . .
H6Q H 0.2324 0.2639 -0.0255 0.027 Uiso 1 1 calc R U . . .
O2 O -0.3759(4) 0.9423(3) 0.0567(2) 0.0361(5) Uani 0.5 1 d D . P . .
H2A H -0.356(4) 0.965(4) -0.0079(14) 0.058(14) Uiso 0.5 1 d D . P . .
H2B H -0.479(3) 0.961(4) 0.070(2) 0.090(19) Uiso 0.5 1 d D . P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 O1B 2.190(5) . ?
Mn1 N1P 2.2430(11) . ?
Mn1 N2R 2.2493(10) . ?
Mn1 N1Q 2.2500(10) . ?
Mn1 O1A 2.329(4) 1_455 ?
Mn1 Cl1B 2.3463(9) . ?
Mn1 Cl1A 2.4619(9) . ?
Mn1 Cl2 2.5700(3) . ?
O1A Mn1 2.329(4) 1_655 ?
O1A H1A 0.8400(10) . ?
O1A H1B 0.8400(10) . ?
O1B H1C 0.8400(10) . ?
O1B H1D 0.8400(10) . ?
N1P C2P 1.3340(16) . ?
N1P C6P 1.3531(15) . ?
C2P N1R 1.3872(15) . ?
C2P C3P 1.3995(17) . ?
C3P C4P 1.3803(19) . ?
C3P H3P 0.9500 . ?
C4P C5P 1.389(2) . ?
C4P H4P 0.9500 . ?
C5P C6P 1.375(2) . ?
C5P H5P 0.9500 . ?
C6P H6P 0.9500 . ?
N1R N2R 1.3576(14) . ?
N1R H1R 0.8800 . ?
N2R C2R 1.2866(14) . ?
C2R C2Q 1.4855(16) . ?
C2R C1M 1.4918(16) . ?
C1M H2M 0.9800 . ?
C1M H1M 0.9800 . ?
C1M H3M 0.9800 . ?
N1Q C6Q 1.3364(16) . ?
N1Q C2Q 1.3528(15) . ?
C2Q C3Q 1.3898(16) . ?
C3Q C4Q 1.3907(18) . ?
C3Q H3Q 0.9500 . ?
C4Q C5Q 1.374(2) . ?
C4Q H4Q 0.9500 . ?
C5Q C6Q 1.3884(18) . ?
C5Q H5Q 0.9500 . ?
C6Q H6Q 0.9500 . ?
O2 H2A 0.8402(10) . ?
O2 H2B 0.8401(10) . ?

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
O1B Mn1 N1P 83.49(13) . . ?
O1B Mn1 N2R 78.23(11) . . ?
N1P Mn1 N2R 71.02(4) . . ?
O1B Mn1 N1Q 85.58(13) . . ?
N1P Mn1 N1Q 141.97(4) . . ?
N2R Mn1 N1Q 71.12(4) . . ?
N1P Mn1 O1A 91.44(9) . 1_455 ?
N2R Mn1 O1A 89.00(10) . 1_455 ?
N1Q Mn1 O1A 84.50(9) . 1_455 ?
O1B Mn1 Cl1B 92.29(11) . . ?
N1P Mn1 Cl1B 94.77(8) . . ?
N2R Mn1 Cl1B 163.56(7) . . ?
N1Q Mn1 Cl1B 122.02(8) . . ?
N1P Mn1 Cl1A 110.23(6) . . ?
N2R Mn1 Cl1A 172.76(3) . . ?
N1Q Mn1 Cl1A 106.89(6) . . ?
O1A Mn1 Cl1A 83.85(10) 1_455 . ?
O1B Mn1 Cl2 168.23(11) . . ?
N1P Mn1 Cl2 92.62(3) . . ?
N2R Mn1 Cl2 90.00(3) . . ?
N1Q Mn1 Cl2 90.79(3) . . ?
O1A Mn1 Cl2 175.26(9) 1_455 . ?
Cl1B Mn1 Cl2 99.11(3) . . ?
Cl1A Mn1 Cl2 97.02(2) . . ?
Mn1 O1A H1A 118.1(18) 1_655 . ?
Mn1 O1A H1B 111(2) 1_655 . ?
H1A O1A H1B 109.27(18) . . ?
Mn1 O1B H1C 127.0(18) . . ?
Mn1 O1B H1D 119(2) . . ?
H1C O1B H1D 109.27(19) . . ?
C2P N1P C6P 117.69(11) . . ?
C2P N1P Mn1 117.69(8) . . ?
C6P N1P Mn1 124.56(9) . . ?
N1P C2P N1R 117.61(11) . . ?
N1P C2P C3P 122.93(11) . . ?
N1R C2P C3P 119.46(11) . . ?
C4P C3P C2P 118.19(13) . . ?
C4P C3P H3P 120.9 . . ?
C2P C3P H3P 120.9 . . ?
C3P C4P C5P 119.58(13) . . ?
C3P C4P H4P 120.2 . . ?
C5P C4P H4P 120.2 . . ?
C6P C5P C4P 118.37(12) . . ?
C6P C5P H5P 120.8 . . ?
C4P C5P H5P 120.8 . . ?
N1P C6P C5P 123.24(13) . . ?
N1P C6P H6P 118.4 . . ?
C5P C6P H6P 118.4 . . ?
N2R N1R C2P 116.32(10) . . ?
N2R N1R H1R 121.8 . . ?
C2P N1R H1R 121.8 . . ?
C2R N2R N1R 121.55(10) . . ?
C2R N2R Mn1 121.01(8) . . ?
N1R N2R Mn1 117.23(7) . . ?
N2R C2R C2Q 114.01(10) . . ?
N2R C2R C1M 124.52(11) . . ?
C2Q C2R C1M 121.44(10) . . ?
C2R C1M H2M 109.5 . . ?
C2R C1M H1M 109.5 . . ?
H2M C1M H1M 109.5 . . ?
C2R C1M H3M 109.5 . . ?
H2M C1M H3M 109.5 . . ?
H1M C1M H3M 109.5 . . ?
C6Q N1Q C2Q 118.64(10) . . ?
C6Q N1Q Mn1 124.30(8) . . ?
C2Q N1Q Mn1 116.88(8) . . ?
N1Q C2Q C3Q 121.71(11) . . ?
N1Q C2Q C2R 116.39(10) . . ?
C3Q C2Q C2R 121.89(11) . . ?
C2Q C3Q C4Q 118.90(12) . . ?
C2Q C3Q H3Q 120.5 . . ?
C4Q C3Q H3Q 120.5 . . ?
C5Q C4Q C3Q 119.14(12) . . ?
C5Q C4Q H4Q 120.4 . . ?
C3Q C4Q H4Q 120.4 . . ?
C4Q C5Q C6Q 118.99(12) . . ?
C4Q C5Q H5Q 120.5 . . ?
C6Q C5Q H5Q 120.5 . . ?
N1Q C6Q C5Q 122.53(12) . . ?
N1Q C6Q H6Q 118.7 . . ?
C5Q C6Q H6Q 118.7 . . ?
H2A O2 H2B 109.24(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
C6P N1P C2P N1R -179.27(11) . . . . ?
Mn1 N1P C2P N1R 3.23(14) . . . . ?
C6P N1P C2P C3P 0.28(18) . . . . ?
Mn1 N1P C2P C3P -177.22(9) . . . . ?
N1P C2P C3P C4P -0.80(19) . . . . ?
N1R C2P C3P C4P 178.74(11) . . . . ?
C2P C3P C4P C5P 0.85(19) . . . . ?
C3P C4P C5P C6P -0.4(2) . . . . ?
C2P N1P C6P C5P 0.18(19) . . . . ?
Mn1 N1P C6P C5P 177.49(10) . . . . ?
C4P C5P C6P N1P -0.1(2) . . . . ?
N1P C2P N1R N2R -4.25(16) . . . . ?
C3P C2P N1R N2R 176.19(11) . . . . ?
C2P N1R N2R C2R 177.90(11) . . . . ?
C2P N1R N2R Mn1 3.22(13) . . . . ?
N1R N2R C2R C2Q -179.20(10) . . . . ?
Mn1 N2R C2R C2Q -4.72(14) . . . . ?
N1R N2R C2R C1M -1.01(18) . . . . ?
Mn1 N2R C2R C1M 173.48(9) . . . . ?
C6Q N1Q C2Q C3Q -3.24(17) . . . . ?
Mn1 N1Q C2Q C3Q 172.12(9) . . . . ?
C6Q N1Q C2Q C2R 176.44(10) . . . . ?
Mn1 N1Q C2Q C2R -8.20(13) . . . . ?
N2R C2R C2Q N1Q 8.45(15) . . . . ?
C1M C2R C2Q N1Q -169.81(11) . . . . ?
N2R C2R C2Q C3Q -171.87(11) . . . . ?
C1M C2R C2Q C3Q 9.87(17) . . . . ?
N1Q C2Q C3Q C4Q 1.98(18) . . . . ?
C2R C2Q C3Q C4Q -177.69(11) . . . . ?
C2Q C3Q C4Q C5Q 0.75(19) . . . . ?
C3Q C4Q C5Q C6Q -2.11(19) . . . . ?
C2Q N1Q C6Q C5Q 1.81(18) . . . . ?
Mn1 N1Q C6Q C5Q -173.17(9) . . . . ?
C4Q C5Q C6Q N1Q 0.9(2) . . . . ?

_refine_diff_density_max         0.440
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.053

# start Validation Reply Form
_vrf_PLAT420_cr170412_0m         
;
PROBLEM: D-H Without Acceptor      *O2     -- *H2A    ...     Please Check 
RESPONSE: This hydrogen atom belongs to a water molecule. A residual
density peak was observed at the H2A position before placing the atom.
With H2A placed and restrained, there were no remaining residual
density peaks close to O2. Hence, this hydrogen atom is simply not
involved in any hydrogen bond.
;
# end Validation Reply Form

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_cr040713_0m
_database_code_depnum_ccdc_archive 'CCDC 1510883'
_audit_update_record             
;
2016-10-20 deposited with the CCDC.
2017-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 Cl4 N8 Zn2'
_chemical_formula_weight         697.05

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'
Zn Zn 0.2839 1.4301 '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                   18.739(3)
_cell_length_b                   7.8233(12)
_cell_length_c                   18.969(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.870(5)
_cell_angle_gamma                90
_cell_volume                     2747.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    9983
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      30.08

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    2.166
_shelx_estimated_absorpt_T_min   0.737
_shelx_estimated_absorpt_T_max   0.863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7371
_exptl_absorpt_correction_T_max  0.8632
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Microfocus
_diffrn_measurement_device_type  'Photon 100 CMOS-detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28679
_diffrn_reflns_av_unetI/netI     0.1400
_diffrn_reflns_av_R_equivalents  0.1004
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.173
_diffrn_reflns_theta_max         30.196
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             8061
_reflns_number_gt                4824
_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       'APEX2 v2012.2-0'
_computing_cell_refinement       'SAINT V8.18C (Bruker AXS Inc.)'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc.)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0410P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8061
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1377
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.0992
_refine_ls_wR_factor_gt          0.0858
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_restrained_S_all      0.964
_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
Zn1 Zn 0.95789(2) 0.66028(4) 0.35094(2) 0.02033(9) Uani 1 1 d . . . . .
Zn2 Zn 0.65253(2) 0.86234(4) 0.53030(2) 0.02075(9) Uani 1 1 d . . . . .
Cl1 Cl 0.98316(4) 0.91532(9) 0.30400(4) 0.02593(18) Uani 1 1 d . . . . .
Cl2 Cl 1.00595(5) 0.44802(9) 0.29066(4) 0.02882(19) Uani 1 1 d . . . . .
Cl3 Cl 0.71531(4) 0.61089(9) 0.54461(4) 0.02502(17) Uani 1 1 d . . . . .
Cl4 Cl 0.69928(5) 1.01539(10) 0.44815(4) 0.02978(19) Uani 1 1 d . . . . .
N1 N 0.84568(14) 0.6056(3) 0.31358(12) 0.0218(6) Uani 1 1 d . . . . .
N2 N 0.82993(13) 0.6972(3) 0.42574(12) 0.0236(6) Uani 1 1 d . . . . .
H2 H 0.8028 0.7366 0.4561 0.028 Uiso 1 1 calc R U . . .
N3 N 0.90289(13) 0.7007(3) 0.44022(12) 0.0194(5) Uani 1 1 d . . . . .
N4 N 1.03979(14) 0.6750(3) 0.44562(12) 0.0200(5) Uani 1 1 d . . . . .
N5 N 0.69990(14) 0.9907(3) 0.62617(12) 0.0210(6) Uani 1 1 d . . . . .
N6 N 0.59515(14) 0.9131(3) 0.66707(12) 0.0248(6) Uani 1 1 d . . . . .
H6N H 0.5684 0.8989 0.7009 0.030 Uiso 1 1 calc R U . . .
N7 N 0.57265(14) 0.8615(3) 0.59906(12) 0.0207(5) Uani 1 1 d . . . . .
N8 N 0.55188(13) 0.7827(3) 0.46575(12) 0.0216(5) Uani 1 1 d . . . . .
C1 C 0.80044(17) 0.6286(3) 0.36078(15) 0.0197(6) Uani 1 1 d . . . . .
C2 C 0.93761(16) 0.7519(4) 0.49973(15) 0.0193(6) Uani 1 1 d . . . . .
C3 C 1.01678(16) 0.7365(3) 0.50474(14) 0.0171(6) Uani 1 1 d . . . . .
C4 C 1.11067(17) 0.6542(3) 0.44649(16) 0.0230(7) Uani 1 1 d . . . . .
H4 H 1.1269 0.6106 0.4050 0.028 Uiso 1 1 calc R U . . .
C5 C 1.16131(17) 0.6934(4) 0.50507(17) 0.0263(7) Uani 1 1 d . . . . .
H5 H 1.2114 0.6770 0.5040 0.032 Uiso 1 1 calc R U . . .
C6 C 1.13763(17) 0.7569(4) 0.56526(16) 0.0274(7) Uani 1 1 d . . . . .
H6 H 1.1713 0.7852 0.6063 0.033 Uiso 1 1 calc R U . . .
C7 C 1.06496(17) 0.7789(4) 0.56534(15) 0.0238(7) Uani 1 1 d . . . . .
H7 H 1.0478 0.8227 0.6064 0.029 Uiso 1 1 calc R U . . .
C8 C 0.90323(18) 0.8196(4) 0.55977(15) 0.0279(7) Uani 1 1 d . . . . .
H8A H 0.8523 0.8455 0.5426 0.042 Uiso 1 1 calc R U . . .
H8B H 0.9282 0.9240 0.5784 0.042 Uiso 1 1 calc R U . . .
H8C H 0.9065 0.7338 0.5978 0.042 Uiso 1 1 calc R U . . .
C9 C 0.72726(17) 0.5910(4) 0.34647(16) 0.0279(7) Uani 1 1 d . . . . .
H9 H 0.6971 0.6068 0.3818 0.033 Uiso 1 1 calc R U . . .
C10 C 0.69963(19) 0.5304(4) 0.28021(17) 0.0318(8) Uani 1 1 d . . . . .
H10 H 0.6497 0.5037 0.2686 0.038 Uiso 1 1 calc R U . . .
C11 C 0.74572(19) 0.5087(4) 0.23021(16) 0.0298(8) Uani 1 1 d . . . . .
H11 H 0.7277 0.4693 0.1835 0.036 Uiso 1 1 calc R U . . .
C12 C 0.81745(18) 0.5449(4) 0.24924(15) 0.0274(7) Uani 1 1 d . . . . .
H12 H 0.8489 0.5261 0.2152 0.033 Uiso 1 1 calc R U . . .
C13 C 0.76692(18) 1.0568(4) 0.63845(16) 0.0279(7) Uani 1 1 d . . . . .
H13 H 0.7935 1.0624 0.5997 0.033 Uiso 1 1 calc R U . . .
C14 C 0.7990(2) 1.1166(4) 0.70368(17) 0.0328(8) Uani 1 1 d . . . . .
H14 H 0.8474 1.1572 0.7108 0.039 Uiso 1 1 calc R U . . .
C15 C 0.7580(2) 1.1155(4) 0.75918(17) 0.0321(8) Uani 1 1 d . . . . .
H15 H 0.7779 1.1582 0.8049 0.038 Uiso 1 1 calc R U . . .
C16 C 0.68921(19) 1.0530(4) 0.74761(15) 0.0284(8) Uani 1 1 d . . . . .
H16 H 0.6604 1.0531 0.7847 0.034 Uiso 1 1 calc R U . . .
C17 C 0.66217(17) 0.9888(3) 0.68021(15) 0.0209(7) Uani 1 1 d . . . . .
C18 C 0.51011(17) 0.7937(4) 0.57922(15) 0.0216(7) Uani 1 1 d . . . . .
C19 C 0.49655(16) 0.7514(3) 0.50220(15) 0.0208(6) Uani 1 1 d . . . . .
C20 C 0.54252(18) 0.7497(4) 0.39596(16) 0.0272(7) Uani 1 1 d . . . . .
H20 H 0.5810 0.7742 0.3703 0.033 Uiso 1 1 calc R U . . .
C21 C 0.47975(18) 0.6816(4) 0.35930(16) 0.0277(7) Uani 1 1 d . . . . .
H21 H 0.4753 0.6578 0.3097 0.033 Uiso 1 1 calc R U . . .
C22 C 0.42374(18) 0.6492(4) 0.39641(17) 0.0298(8) Uani 1 1 d . . . . .
H22 H 0.3797 0.6030 0.3726 0.036 Uiso 1 1 calc R U . . .
C23 C 0.43191(17) 0.6842(4) 0.46845(16) 0.0258(7) Uani 1 1 d . . . . .
H23 H 0.3936 0.6623 0.4946 0.031 Uiso 1 1 calc R U . . .
C24 C 0.45651(17) 0.7599(4) 0.62702(16) 0.0302(8) Uani 1 1 d . . . . .
H24A H 0.4815 0.7404 0.6756 0.045 Uiso 1 1 calc R U . . .
H24B H 0.4282 0.6584 0.6104 0.045 Uiso 1 1 calc R U . . .
H24C H 0.4242 0.8586 0.6267 0.045 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
Zn1 N3 2.137(2) . ?
Zn1 N1 2.156(3) . ?
Zn1 N4 2.178(2) . ?
Zn1 Cl1 2.2645(8) . ?
Zn1 Cl2 2.2789(8) . ?
Zn2 N7 2.132(2) . ?
Zn2 N5 2.146(2) . ?
Zn2 N8 2.175(3) . ?
Zn2 Cl4 2.2473(8) . ?
Zn2 Cl3 2.2867(9) . ?
N1 C1 1.337(4) . ?
N1 C12 1.340(4) . ?
N2 N3 1.353(3) . ?
N2 C1 1.379(4) . ?
N2 H2 0.8800 . ?
N3 C2 1.277(3) . ?
N4 C4 1.336(4) . ?
N4 C3 1.351(3) . ?
N5 C17 1.332(3) . ?
N5 C13 1.345(4) . ?
N6 N7 1.356(3) . ?
N6 C17 1.376(4) . ?
N6 H6N 0.8800 . ?
N7 C18 1.288(4) . ?
N8 C20 1.334(4) . ?
N8 C19 1.354(4) . ?
C1 C9 1.388(4) . ?
C2 C3 1.477(4) . ?
C2 C8 1.490(4) . ?
C3 C7 1.388(4) . ?
C4 C5 1.380(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.373(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.368(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.367(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.372(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.397(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.364(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.394(4) . ?
C16 H16 0.9500 . ?
C18 C24 1.477(4) . ?
C18 C19 1.481(4) . ?
C19 C23 1.384(4) . ?
C20 C21 1.378(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.375(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.379(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
N3 Zn1 N1 74.03(9) . . ?
N3 Zn1 N4 72.74(9) . . ?
N1 Zn1 N4 144.00(9) . . ?
N3 Zn1 Cl1 109.68(7) . . ?
N1 Zn1 Cl1 107.35(7) . . ?
N4 Zn1 Cl1 96.56(6) . . ?
N3 Zn1 Cl2 141.39(7) . . ?
N1 Zn1 Cl2 97.54(7) . . ?
N4 Zn1 Cl2 99.75(7) . . ?
Cl1 Zn1 Cl2 108.78(3) . . ?
N7 Zn2 N5 73.78(9) . . ?
N7 Zn2 N8 73.37(9) . . ?
N5 Zn2 N8 145.12(9) . . ?
N7 Zn2 Cl4 144.25(7) . . ?
N5 Zn2 Cl4 100.59(7) . . ?
N8 Zn2 Cl4 99.15(7) . . ?
N7 Zn2 Cl3 108.76(7) . . ?
N5 Zn2 Cl3 99.44(7) . . ?
N8 Zn2 Cl3 101.89(7) . . ?
Cl4 Zn2 Cl3 106.99(3) . . ?
C1 N1 C12 117.1(3) . . ?
C1 N1 Zn1 116.11(19) . . ?
C12 N1 Zn1 126.7(2) . . ?
N3 N2 C1 116.3(2) . . ?
N3 N2 H2 121.9 . . ?
C1 N2 H2 121.9 . . ?
C2 N3 N2 123.2(2) . . ?
C2 N3 Zn1 120.3(2) . . ?
N2 N3 Zn1 115.58(17) . . ?
C4 N4 C3 118.5(3) . . ?
C4 N4 Zn1 125.2(2) . . ?
C3 N4 Zn1 115.40(19) . . ?
C17 N5 C13 117.6(3) . . ?
C17 N5 Zn2 116.6(2) . . ?
C13 N5 Zn2 125.44(19) . . ?
N7 N6 C17 116.2(2) . . ?
N7 N6 H6N 121.9 . . ?
C17 N6 H6N 121.9 . . ?
C18 N7 N6 122.4(2) . . ?
C18 N7 Zn2 121.02(19) . . ?
N6 N7 Zn2 115.89(19) . . ?
C20 N8 C19 118.6(3) . . ?
C20 N8 Zn2 125.7(2) . . ?
C19 N8 Zn2 115.46(19) . . ?
N1 C1 N2 116.3(3) . . ?
N1 C1 C9 123.4(3) . . ?
N2 C1 C9 120.3(3) . . ?
N3 C2 C3 113.6(3) . . ?
N3 C2 C8 124.5(3) . . ?
C3 C2 C8 121.9(3) . . ?
N4 C3 C7 121.5(3) . . ?
N4 C3 C2 114.9(3) . . ?
C7 C3 C2 123.5(3) . . ?
N4 C4 C5 122.8(3) . . ?
N4 C4 H4 118.6 . . ?
C5 C4 H4 118.6 . . ?
C6 C5 C4 118.5(3) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C7 C6 C5 119.4(3) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C3 119.2(3) . . ?
C6 C7 H7 120.4 . . ?
C3 C7 H7 120.4 . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C1 118.4(3) . . ?
C10 C9 H9 120.8 . . ?
C1 C9 H9 120.8 . . ?
C9 C10 C11 118.9(3) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 H10 120.6 . . ?
C12 C11 C10 119.0(3) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
N1 C12 C11 123.2(3) . . ?
N1 C12 H12 118.4 . . ?
C11 C12 H12 118.4 . . ?
N5 C13 C14 123.7(3) . . ?
N5 C13 H13 118.1 . . ?
C14 C13 H13 118.1 . . ?
C13 C14 C15 117.5(3) . . ?
C13 C14 H14 121.3 . . ?
C15 C14 H14 121.3 . . ?
C16 C15 C14 119.8(3) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 118.5(3) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
N5 C17 N6 116.3(3) . . ?
N5 C17 C16 122.7(3) . . ?
N6 C17 C16 120.9(3) . . ?
N7 C18 C24 124.6(3) . . ?
N7 C18 C19 113.0(3) . . ?
C24 C18 C19 122.4(3) . . ?
N8 C19 C23 121.1(3) . . ?
N8 C19 C18 115.8(3) . . ?
C23 C19 C18 123.1(3) . . ?
N8 C20 C21 123.2(3) . . ?
N8 C20 H20 118.4 . . ?
C21 C20 H20 118.4 . . ?
C22 C21 C20 118.2(3) . . ?
C22 C21 H21 120.9 . . ?
C20 C21 H21 120.9 . . ?
C21 C22 C23 119.6(3) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C22 C23 C19 119.3(3) . . ?
C22 C23 H23 120.3 . . ?
C19 C23 H23 120.3 . . ?
C18 C24 H24A 109.5 . . ?
C18 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C18 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N2 N3 C2 -176.1(3) . . . . ?
C1 N2 N3 Zn1 15.1(3) . . . . ?
C17 N6 N7 C18 -177.8(3) . . . . ?
C17 N6 N7 Zn2 11.5(3) . . . . ?
C12 N1 C1 N2 -177.6(3) . . . . ?
Zn1 N1 C1 N2 4.9(3) . . . . ?
C12 N1 C1 C9 0.9(4) . . . . ?
Zn1 N1 C1 C9 -176.6(2) . . . . ?
N3 N2 C1 N1 -13.2(4) . . . . ?
N3 N2 C1 C9 168.2(3) . . . . ?
N2 N3 C2 C3 177.2(2) . . . . ?
Zn1 N3 C2 C3 -14.5(3) . . . . ?
N2 N3 C2 C8 -2.2(5) . . . . ?
Zn1 N3 C2 C8 166.1(2) . . . . ?
C4 N4 C3 C7 0.4(4) . . . . ?
Zn1 N4 C3 C7 -169.4(2) . . . . ?
C4 N4 C3 C2 -178.7(2) . . . . ?
Zn1 N4 C3 C2 11.5(3) . . . . ?
N3 C2 C3 N4 1.4(4) . . . . ?
C8 C2 C3 N4 -179.2(3) . . . . ?
N3 C2 C3 C7 -177.7(3) . . . . ?
C8 C2 C3 C7 1.7(4) . . . . ?
C3 N4 C4 C5 -0.2(4) . . . . ?
Zn1 N4 C4 C5 168.5(2) . . . . ?
N4 C4 C5 C6 -0.1(4) . . . . ?
C4 C5 C6 C7 0.2(5) . . . . ?
C5 C6 C7 C3 0.1(5) . . . . ?
N4 C3 C7 C6 -0.4(4) . . . . ?
C2 C3 C7 C6 178.7(3) . . . . ?
N1 C1 C9 C10 -1.4(5) . . . . ?
N2 C1 C9 C10 177.0(3) . . . . ?
C1 C9 C10 C11 0.2(5) . . . . ?
C9 C10 C11 C12 1.4(5) . . . . ?
C1 N1 C12 C11 0.9(4) . . . . ?
Zn1 N1 C12 C11 178.0(2) . . . . ?
C10 C11 C12 N1 -2.0(5) . . . . ?
C17 N5 C13 C14 2.3(5) . . . . ?
Zn2 N5 C13 C14 -170.5(2) . . . . ?
N5 C13 C14 C15 -3.2(5) . . . . ?
C13 C14 C15 C16 1.4(5) . . . . ?
C14 C15 C16 C17 1.0(5) . . . . ?
C13 N5 C17 N6 -177.0(3) . . . . ?
Zn2 N5 C17 N6 -3.6(3) . . . . ?
C13 N5 C17 C16 0.4(4) . . . . ?
Zn2 N5 C17 C16 173.9(2) . . . . ?
N7 N6 C17 N5 -5.2(4) . . . . ?
N7 N6 C17 C16 177.3(3) . . . . ?
C15 C16 C17 N5 -2.0(5) . . . . ?
C15 C16 C17 N6 175.3(3) . . . . ?
N6 N7 C18 C24 -1.5(5) . . . . ?
Zn2 N7 C18 C24 168.7(2) . . . . ?
N6 N7 C18 C19 178.5(2) . . . . ?
Zn2 N7 C18 C19 -11.2(3) . . . . ?
C20 N8 C19 C23 1.0(4) . . . . ?
Zn2 N8 C19 C23 -173.7(2) . . . . ?
C20 N8 C19 C18 -179.0(3) . . . . ?
Zn2 N8 C19 C18 6.3(3) . . . . ?
N7 C18 C19 N8 2.7(4) . . . . ?
C24 C18 C19 N8 -177.2(3) . . . . ?
N7 C18 C19 C23 -177.2(3) . . . . ?
C24 C18 C19 C23 2.8(4) . . . . ?
C19 N8 C20 C21 -1.5(4) . . . . ?
Zn2 N8 C20 C21 172.6(2) . . . . ?
N8 C20 C21 C22 1.2(5) . . . . ?
C20 C21 C22 C23 -0.4(5) . . . . ?
C21 C22 C23 C19 0.0(5) . . . . ?
N8 C19 C23 C22 -0.3(4) . . . . ?
C18 C19 C23 C22 179.7(3) . . . . ?

_refine_diff_density_max         0.689
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.114

