# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_111
_database_code_depnum_ccdc_archive 'CCDC 1476562'
_audit_update_record             
;
2016-04-26 deposited with the CCDC.
2018-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H17 Cl4 N2 Zn'
_chemical_formula_weight         348.41

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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

_cell_length_a                   9.9794(7)
_cell_length_b                   12.3968(9)
_cell_length_c                   11.2336(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.857(6)
_cell_angle_gamma                90.00
_cell_volume                     1386.59(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    3281
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      27.37
_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             708
_exptl_absorpt_coefficient_mu    2.514
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5396
_exptl_absorpt_correction_T_max  0.6604
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2549
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0461
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         25.68
_reflns_number_total             2548
_reflns_number_gt                2025
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2760P)²+0.0000P] 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         2549
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1171
_refine_ls_R_factor_gt           0.0990
_refine_ls_wR_factor_ref         0.3415
_refine_ls_wR_factor_gt          0.3022
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.24373(11) 0.42209(9) 0.21001(10) 0.0289(5) Uani 1 1 d . . .
Cl2 Cl 0.2490(2) 0.60717(16) 0.22595(19) 0.0226(6) Uani 1 1 d . . .
Cl3 Cl 0.4220(2) 0.3572(2) 0.1141(2) 0.0317(7) Uani 1 1 d . . .
Cl4 Cl 0.0672(2) 0.3533(2) 0.0917(2) 0.0303(7) Uani 1 1 d . . .
Cl5 Cl 0.2338(4) 0.3525(2) 0.3950(2) 0.0476(9) Uani 1 1 d . . .
N1 N 0.2401(9) 0.9641(7) 0.1771(8) 0.0301(19) Uani 1 1 d . . .
C2 C 0.2532(13) 0.9679(10) 0.3976(9) 0.038(3) Uani 1 1 d . . .
H2A H 0.3384 0.9538 0.4416 0.046 Uiso 1 1 calc R . .
H2B H 0.1817 0.9521 0.4492 0.046 Uiso 1 1 calc R . .
C4 C 0.1175(10) 1.0376(9) 0.1733(10) 0.032(2) Uani 1 1 d . . .
H4A H 0.0367 0.9944 0.1617 0.039 Uiso 1 1 calc R . .
H4B H 0.1203 1.0867 0.1063 0.039 Uiso 1 1 calc R . .
C5 C 0.1127(13) 1.1027(10) 0.2889(11) 0.039(3) Uani 1 1 d . . .
H5A H 0.0989 1.1786 0.2710 0.047 Uiso 1 1 calc R . .
H5B H 0.0396 1.0777 0.3344 0.047 Uiso 1 1 calc R . .
C7 C 0.3628(13) 1.1136(11) 0.2883(11) 0.046(3) Uani 1 1 d . . .
H7A H 0.3552 1.1876 0.2604 0.055 Uiso 1 1 calc R . .
H7B H 0.4458 1.1066 0.3377 0.055 Uiso 1 1 calc R . .
N11 N 0.2459(8) 1.0863(6) 0.3594(8) 0.0266(18) Uani 1 1 d . . .
C12 C 0.3640(10) 1.0385(8) 0.1842(9) 0.030(2) Uani 1 1 d . . .
H12A H 0.4449 0.9950 0.1914 0.035 Uiso 1 1 calc R . .
H12B H 0.3653 1.0802 0.1111 0.035 Uiso 1 1 calc R . .
C1 C 0.2396(11) 0.8982(9) 0.2896(9) 0.030(2) Uani 1 1 d . . .
H1A H 0.1564 0.8577 0.2896 0.036 Uiso 1 1 calc R . .
H1B H 0.3132 0.8470 0.2919 0.036 Uiso 1 1 calc R . .
C3 C 0.2355(14) 0.8954(10) 0.0688(11) 0.043(3) Uani 1 1 d . . .
H3A H 0.2167 0.9415 0.0000 0.052 Uiso 1 1 calc R . .
H3B H 0.1604 0.8461 0.0725 0.052 Uiso 1 1 calc R . .
C6 C 0.3583(16) 0.8302(12) 0.0479(13) 0.058(4) Uani 1 1 d . . .
H6A H 0.4287 0.8772 0.0253 0.087 Uiso 1 1 calc R . .
H6B H 0.3376 0.7790 -0.0148 0.087 Uiso 1 1 calc R . .
H6C H 0.3873 0.7926 0.1198 0.087 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Zn1 0.0366(8) 0.0268(8) 0.0238(8) -0.0001(4) 0.0062(5) 0.0011(5)
Cl2 0.0403(14) 0.0060(10) 0.0213(12) -0.0022(7) 0.0017(10) -0.0013(8)
Cl3 0.0266(13) 0.0389(15) 0.0298(14) -0.0005(10) 0.0038(10) 0.0004(10)
Cl4 0.0252(12) 0.0385(14) 0.0279(13) 0.0000(10) 0.0065(10) 0.0024(10)
Cl5 0.097(3) 0.0281(14) 0.0190(14) -0.0014(10) 0.0097(14) -0.0005(14)
N1 0.031(5) 0.033(5) 0.025(4) -0.001(4) 0.000(4) -0.002(4)
C2 0.047(7) 0.042(6) 0.025(6) 0.012(5) 0.003(5) 0.011(5)
C4 0.022(5) 0.037(6) 0.037(6) 0.000(5) -0.004(4) 0.000(4)
C5 0.047(7) 0.038(6) 0.033(6) -0.006(5) 0.001(5) 0.005(5)
C7 0.046(7) 0.053(7) 0.041(7) -0.016(6) 0.022(6) -0.024(6)
N11 0.030(4) 0.016(4) 0.034(5) 0.000(3) 0.005(4) 0.004(3)
C12 0.031(5) 0.026(5) 0.033(5) 0.006(4) 0.011(4) 0.004(4)
C1 0.033(6) 0.028(5) 0.029(6) 0.008(4) 0.001(4) -0.008(4)
C3 0.058(8) 0.042(6) 0.030(6) -0.002(5) 0.011(5) 0.010(6)
C6 0.075(10) 0.058(8) 0.043(7) -0.019(6) 0.020(7) -0.017(7)

_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 Cl5 2.258(3) . ?
Zn1 Cl3 2.287(3) . ?
Zn1 Cl4 2.298(3) . ?
Zn1 Cl2 2.302(2) . ?
N1 C3 1.483(14) . ?
N1 C1 1.506(13) . ?
N1 C4 1.524(13) . ?
N1 C12 1.540(13) . ?
C2 C1 1.488(16) . ?
C2 N11 1.529(13) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C4 C5 1.532(16) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 N11 1.514(14) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C7 C12 1.496(15) . ?
C7 N11 1.496(14) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C3 C6 1.500(18) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 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
Cl5 Zn1 Cl3 112.51(12) . . ?
Cl5 Zn1 Cl4 108.11(12) . . ?
Cl3 Zn1 Cl4 100.80(9) . . ?
Cl5 Zn1 Cl2 108.15(10) . . ?
Cl3 Zn1 Cl2 111.88(10) . . ?
Cl4 Zn1 Cl2 115.32(10) . . ?
C3 N1 C1 112.0(8) . . ?
C3 N1 C4 109.9(8) . . ?
C1 N1 C4 107.5(8) . . ?
C3 N1 C12 111.5(9) . . ?
C1 N1 C12 109.3(8) . . ?
C4 N1 C12 106.5(8) . . ?
C1 C2 N11 109.2(8) . . ?
C1 C2 H2A 109.8 . . ?
N11 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
N11 C2 H2B 109.8 . . ?
H2A C2 H2B 108.3 . . ?
N1 C4 C5 111.2(8) . . ?
N1 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
N1 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
N11 C5 C4 107.2(9) . . ?
N11 C5 H5A 110.3 . . ?
C4 C5 H5A 110.3 . . ?
N11 C5 H5B 110.3 . . ?
C4 C5 H5B 110.3 . . ?
H5A C5 H5B 108.5 . . ?
C12 C7 N11 108.9(8) . . ?
C12 C7 H7A 109.9 . . ?
N11 C7 H7A 109.9 . . ?
C12 C7 H7B 109.9 . . ?
N11 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
C7 N11 C5 112.2(10) . . ?
C7 N11 C2 110.1(9) . . ?
C5 N11 C2 107.4(8) . . ?
C7 C12 N1 111.4(8) . . ?
C7 C12 H12A 109.4 . . ?
N1 C12 H12A 109.4 . . ?
C7 C12 H12B 109.4 . . ?
N1 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C2 C1 N1 111.3(9) . . ?
C2 C1 H1A 109.4 . . ?
N1 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
N1 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
N1 C3 C6 117.2(10) . . ?
N1 C3 H3A 108.0 . . ?
C6 C3 H3A 108.0 . . ?
N1 C3 H3B 108.0 . . ?
C6 C3 H3B 108.0 . . ?
H3A C3 H3B 107.2 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 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
C3 N1 C4 C5 175.0(10) . . . . ?
C1 N1 C4 C5 52.9(11) . . . . ?
C12 N1 C4 C5 -64.1(11) . . . . ?
N1 C4 C5 N11 10.0(13) . . . . ?
C12 C7 N11 C5 -63.2(13) . . . . ?
C12 C7 N11 C2 56.4(13) . . . . ?
C4 C5 N11 C7 54.4(12) . . . . ?
C4 C5 N11 C2 -66.8(11) . . . . ?
C1 C2 N11 C7 -64.3(12) . . . . ?
C1 C2 N11 C5 58.2(11) . . . . ?
N11 C7 C12 N1 4.7(14) . . . . ?
C3 N1 C12 C7 175.6(10) . . . . ?
C1 N1 C12 C7 -60.0(12) . . . . ?
C4 N1 C12 C7 55.8(11) . . . . ?
N11 C2 C1 N1 7.0(12) . . . . ?
C3 N1 C1 C2 176.3(10) . . . . ?
C4 N1 C1 C2 -62.9(10) . . . . ?
C12 N1 C1 C2 52.2(11) . . . . ?
C1 N1 C3 C6 -69.9(13) . . . . ?
C4 N1 C3 C6 170.8(10) . . . . ?
C12 N1 C3 C6 53.0(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        25.68
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         2.822
_refine_diff_density_min         -1.079
_refine_diff_density_rms         0.269
####################################################################### 
# 
# 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_111_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1476564'
_audit_update_record             
;
2016-04-26 deposited with the CCDC.
2018-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H17 Cl4 N2 Zn'
_chemical_formula_weight         348.41

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'Pnma '

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

_cell_length_a                   11.3016(18)
_cell_length_b                   10.0982(16)
_cell_length_c                   12.4665(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1422.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3699
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      27.20
_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             708
_exptl_absorpt_coefficient_mu    2.450
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5471
_exptl_absorpt_correction_T_max  0.6668
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9281
_diffrn_reflns_av_R_equivalents  0.1092
_diffrn_reflns_av_sigmaI/netI    0.0518
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.16
_diffrn_reflns_theta_max         27.45
_reflns_number_total             1714
_reflns_number_gt                1276
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1030P)²+3.0449P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1714
_refine_ls_number_parameters     86
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0598
_refine_ls_wR_factor_ref         0.1904
_refine_ls_wR_factor_gt          0.1720
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.28612(7) 0.2500 0.42325(7) 0.0424(3) Uani 1 2 d S . .
Cl2 Cl 0.39261(12) 0.07487(13) 0.35702(12) 0.0487(4) Uani 1 1 d . . .
Cl1 Cl 0.27082(17) 0.2500 0.60648(13) 0.0483(5) Uani 1 2 d S . .
Cl3 Cl 0.10126(17) 0.2500 0.35287(17) 0.0793(10) Uani 1 2 d S . .
N1 N 0.8194(5) 0.2500 0.5328(5) 0.0369(13) Uani 1 2 d S . .
C6 C 0.6011(7) 0.2500 0.5290(6) 0.0458(18) Uani 1 2 d S . .
H6A H 0.5535 0.1722 0.5439 0.055 Uiso 0.50 1 calc PR . .
H6B H 0.5535 0.3278 0.5439 0.055 Uiso 0.50 1 calc PR . .
C4 C 0.7093(6) 0.2500 0.6002(6) 0.0391(16) Uani 1 2 d S . .
H4A H 0.7084 0.3278 0.6458 0.047 Uiso 0.50 1 calc PR . .
H4B H 0.7084 0.1722 0.6458 0.047 Uiso 0.50 1 calc PR . .
C3 C 0.8185(5) 0.1286(6) 0.4624(5) 0.0466(13) Uani 1 1 d . . .
H3A H 0.8196 0.0498 0.5069 0.056 Uiso 1 1 calc R . .
H3B H 0.8888 0.1279 0.4178 0.056 Uiso 1 1 calc R . .
C5 C 0.7089(5) 0.1275(7) 0.3917(5) 0.0533(15) Uani 1 1 d . . .
H5A H 0.7319 0.1259 0.3168 0.064 Uiso 1 1 calc R . .
H5B H 0.6621 0.0491 0.4065 0.064 Uiso 1 1 calc R . .
N2 N 0.6371(6) 0.2500 0.4146(5) 0.0431(14) Uani 1 2 d S . .
C2 C 0.9284(8) 0.2500 0.6016(7) 0.066(3) Uani 1 2 d S . .
H2A H 0.9260 0.3279 0.6456 0.079 Uiso 0.50 1 d PR . .
H2B H 0.9954 0.2500 0.5548 0.079 Uiso 1 2 d SR . .
C1 C 0.9510(14) 0.1394(17) 0.6702(11) 0.075(4) Uani 0.50 1 d P . .
H1A H 1.0184 0.1579 0.7145 0.113 Uiso 0.50 1 calc PR . .
H1B H 0.9665 0.0623 0.6273 0.113 Uiso 0.50 1 calc PR . .
H1C H 0.8831 0.1236 0.7148 0.113 Uiso 0.50 1 calc PR . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Zn1 0.0376(5) 0.0495(6) 0.0400(5) 0.000 0.0002(3) 0.000
Cl2 0.0497(8) 0.0331(6) 0.0632(9) 0.0003(6) 0.0013(6) 0.0007(5)
Cl1 0.0476(10) 0.0783(14) 0.0191(7) 0.000 0.0021(7) 0.000
Cl3 0.0303(10) 0.165(3) 0.0421(11) 0.000 0.0023(8) 0.000
N1 0.034(3) 0.040(3) 0.038(3) 0.000 0.003(2) 0.000
C6 0.036(4) 0.054(5) 0.047(4) 0.000 0.005(3) 0.000
C4 0.038(4) 0.046(4) 0.034(3) 0.000 0.007(3) 0.000
C3 0.047(3) 0.043(3) 0.051(3) -0.005(2) 0.004(2) 0.008(2)
C5 0.053(3) 0.053(4) 0.054(3) -0.018(3) -0.005(3) 0.010(3)
N2 0.040(3) 0.045(3) 0.044(3) 0.000 -0.005(3) 0.000
C2 0.042(4) 0.106(8) 0.050(5) 0.000 -0.006(4) 0.000
C1 0.082(9) 0.082(10) 0.062(8) 0.010(7) -0.016(7) 0.033(8)

_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 Cl3 2.266(2) . ?
Zn1 Cl1 2.2907(18) . ?
Zn1 Cl2 2.2930(14) 8_565 ?
Zn1 Cl2 2.2930(14) . ?
N1 C4 1.501(9) . ?
N1 C2 1.501(10) . ?
N1 C3 1.508(6) 8_565 ?
N1 C3 1.508(6) . ?
C6 N2 1.483(10) . ?
C6 C4 1.511(10) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C3 C5 1.521(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C5 N2 1.506(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
N2 C5 1.506(7) 8_565 ?
C2 C1 1.430(15) . ?
C2 C1 1.430(15) 8_565 ?
C2 H2A 0.9600 . ?
C2 H2B 0.9558 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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
Cl3 Zn1 Cl1 108.45(8) . . ?
Cl3 Zn1 Cl2 110.15(5) . 8_565 ?
Cl1 Zn1 Cl2 113.49(5) . 8_565 ?
Cl3 Zn1 Cl2 110.15(5) . . ?
Cl1 Zn1 Cl2 113.49(5) . . ?
Cl2 Zn1 Cl2 100.93(8) 8_565 . ?
C4 N1 C2 111.2(6) . . ?
C4 N1 C3 108.7(4) . 8_565 ?
C2 N1 C3 109.7(4) . 8_565 ?
C4 N1 C3 108.7(4) . . ?
C2 N1 C3 109.7(4) . . ?
C3 N1 C3 108.8(6) 8_565 . ?
N2 C6 C4 110.1(6) . . ?
N2 C6 H6A 109.6 . . ?
C4 C6 H6A 109.6 . . ?
N2 C6 H6B 109.6 . . ?
C4 C6 H6B 109.6 . . ?
H6A C6 H6B 108.2 . . ?
N1 C4 C6 110.0(6) . . ?
N1 C4 H4A 109.7 . . ?
C6 C4 H4A 109.7 . . ?
N1 C4 H4B 109.7 . . ?
C6 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
N1 C3 C5 110.4(5) . . ?
N1 C3 H3A 109.6 . . ?
C5 C3 H3A 109.6 . . ?
N1 C3 H3B 109.6 . . ?
C5 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
N2 C5 C3 108.9(5) . . ?
N2 C5 H5A 109.9 . . ?
C3 C5 H5A 109.9 . . ?
N2 C5 H5B 109.9 . . ?
C3 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
C6 N2 C5 109.2(4) . 8_565 ?
C6 N2 C5 109.2(4) . . ?
C5 N2 C5 110.4(7) 8_565 . ?
C1 C2 C1 102.8(14) . 8_565 ?
C1 C2 N1 119.2(8) . . ?
C1 C2 N1 119.2(8) 8_565 . ?
C1 C2 H2A 107.7 . . ?
C1 C2 H2A 12.2 8_565 . ?
N1 C2 H2A 107.7 . . ?
C1 C2 H2B 102.9 . . ?
C1 C2 H2B 102.9 8_565 . ?
N1 C2 H2B 107.6 . . ?
H2A C2 H2B 111.8 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
C2 N1 C4 C6 180.000(1) . . . . ?
C3 N1 C4 C6 59.1(4) 8_565 . . . ?
C3 N1 C4 C6 -59.1(4) . . . . ?
N2 C6 C4 N1 0.000(1) . . . . ?
C4 N1 C3 C5 58.6(6) . . . . ?
C2 N1 C3 C5 -179.7(5) . . . . ?
C3 N1 C3 C5 -59.6(7) 8_565 . . . ?
N1 C3 C5 N2 0.6(7) . . . . ?
C4 C6 N2 C5 -60.4(4) . . . 8_565 ?
C4 C6 N2 C5 60.4(4) . . . . ?
C3 C5 N2 C6 -60.4(6) . . . . ?
C3 C5 N2 C5 59.7(8) . . . 8_565 ?
C4 N1 C2 C1 63.5(9) . . . . ?
C3 N1 C2 C1 -176.2(9) 8_565 . . . ?
C3 N1 C2 C1 -56.7(11) . . . . ?
C4 N1 C2 C1 -63.5(9) . . . 8_565 ?
C3 N1 C2 C1 56.7(11) 8_565 . . 8_565 ?
C3 N1 C2 C1 176.2(9) . . . 8_565 ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.886
_refine_diff_density_min         -0.755
_refine_diff_density_rms         0.154
####################################################################### 
# 
# 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_222
_database_code_depnum_ccdc_archive 'CCDC 1476563'
_audit_update_record             
;
2016-04-26 deposited with the CCDC.
2018-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H17 Cl4 Co N2'
_chemical_formula_weight         341.97

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   9.969(10)
_cell_length_b                   12.376(12)
_cell_length_c                   11.267(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.250(11)
_cell_angle_gamma                90.00
_cell_volume                     1388(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    233(2)
_cell_measurement_reflns_used    3727
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      26.69

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    1.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6590
_exptl_absorpt_correction_T_max  0.7172
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      233(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_decay_%        ?

_diffrn_reflns_number            2491
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0916
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         25.51
_reflns_number_total             2491
_reflns_number_gt                1963
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1323P)²+15.2661P] 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         2491
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1345
_refine_ls_R_factor_gt           0.1114
_refine_ls_wR_factor_ref         0.2900
_refine_ls_wR_factor_gt          0.2716
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.124
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.25552(16) 0.07792(11) 0.79017(13) 0.0232(5) Uani 1 1 d . . .
Cl1 Cl 0.2504(4) -0.10502(19) 0.7715(3) 0.0337(8) Uani 1 1 d . . .
Cl2 Cl 0.0780(3) 0.1423(3) 0.8875(3) 0.0324(7) Uani 1 1 d . . .
Cl3 Cl 0.4311(3) 0.1460(2) 0.9070(3) 0.0308(7) Uani 1 1 d . . .
Cl4 Cl 0.2656(5) 0.1469(2) 0.6053(2) 0.0497(11) Uani 1 1 d . . .
N1 N 0.7440(9) -0.0862(6) 0.8586(8) 0.022(2) Uani 1 1 d . . .
N2 N 0.7400(10) 0.0360(7) 0.6773(7) 0.022(2) Uani 1 1 d . . .
C1 C 0.7525(13) 0.0303(8) 0.8988(10) 0.027(3) Uani 1 1 d . . .
H1A H 0.8379 0.0431 0.9440 0.032 Uiso 1 1 calc R . .
H1B H 0.6791 0.0467 0.9501 0.032 Uiso 1 1 calc R . .
C2 C 0.7424(13) 0.1038(8) 0.7864(10) 0.029(3) Uani 1 1 d . . .
H2A H 0.6605 0.1475 0.7864 0.035 Uiso 1 1 calc R . .
H2B H 0.8196 0.1529 0.7875 0.035 Uiso 1 1 calc R . .
C3 C 0.6158(13) -0.1031(10) 0.7887(11) 0.031(3) Uani 1 1 d . . .
H3A H 0.5405 -0.0801 0.8349 0.037 Uiso 1 1 calc R . .
H3B H 0.6044 -0.1800 0.7698 0.037 Uiso 1 1 calc R . .
C4 C 0.6175(13) -0.0365(10) 0.6724(11) 0.030(3) Uani 1 1 d . . .
H4A H 0.6198 -0.0852 0.6040 0.036 Uiso 1 1 calc R . .
H4B H 0.5358 0.0075 0.6629 0.036 Uiso 1 1 calc R . .
C5 C 0.8611(14) -0.1126(10) 0.7897(13) 0.036(3) Uani 1 1 d . . .
H5A H 0.8551 -0.1878 0.7624 0.044 Uiso 1 1 calc R . .
H5B H 0.9440 -0.1044 0.8399 0.044 Uiso 1 1 calc R . .
C6 C 0.8638(13) -0.0366(10) 0.6825(10) 0.030(3) Uani 1 1 d . . .
H6A H 0.9452 0.0079 0.6891 0.036 Uiso 1 1 calc R . .
H6B H 0.8655 -0.0791 0.6092 0.036 Uiso 1 1 calc R . .
C7 C 0.7366(15) 0.1061(9) 0.5664(10) 0.034(3) Uani 1 1 d . . .
H7A H 0.7176 0.0597 0.4970 0.041 Uiso 1 1 calc R . .
H7B H 0.6619 0.1573 0.5701 0.041 Uiso 1 1 calc R . .
C8 C 0.8607(19) 0.1681(13) 0.5476(12) 0.054(4) Uani 1 1 d . . .
H8A H 0.8796 0.2162 0.6145 0.081 Uiso 1 1 calc R . .
H8B H 0.8486 0.2102 0.4752 0.081 Uiso 1 1 calc R . .
H8C H 0.9352 0.1185 0.5408 0.081 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Co1 0.0310(9) 0.0142(7) 0.0247(8) 0.0003(6) 0.0052(6) 0.0007(7)
Cl1 0.056(2) 0.0050(10) 0.0405(17) -0.0020(10) 0.0041(15) -0.0016(11)
Cl2 0.0230(16) 0.0355(16) 0.0394(16) -0.0015(13) 0.0077(12) 0.0016(12)
Cl3 0.0207(15) 0.0344(16) 0.0377(16) 0.0013(12) 0.0055(12) -0.0005(12)
Cl4 0.112(3) 0.0190(13) 0.0193(15) -0.0020(11) 0.0101(17) 0.0030(18)
N1 0.025(5) 0.012(4) 0.029(5) 0.004(4) 0.003(4) 0.002(4)
N2 0.036(6) 0.013(4) 0.018(4) 0.004(3) 0.009(4) -0.001(4)
C1 0.037(7) 0.013(5) 0.031(6) -0.005(4) 0.000(5) 0.004(5)
C2 0.037(8) 0.008(4) 0.042(7) -0.002(5) 0.007(6) 0.002(4)
C3 0.027(7) 0.024(6) 0.041(7) 0.002(5) 0.008(5) -0.008(5)
C4 0.029(7) 0.028(6) 0.033(6) 0.002(5) 0.000(5) -0.007(5)
C5 0.038(8) 0.025(6) 0.049(8) 0.008(6) 0.026(6) 0.007(5)
C6 0.036(7) 0.024(6) 0.030(6) -0.003(5) 0.010(5) -0.001(5)
C7 0.058(9) 0.023(5) 0.020(5) -0.002(5) 0.003(6) 0.000(6)
C8 0.091(13) 0.045(8) 0.028(7) 0.004(6) 0.011(8) -0.005(8)

_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
Co1 Cl4 2.259(4) . ?
Co1 Cl1 2.274(3) . ?
Co1 Cl2 2.278(4) . ?
Co1 Cl3 2.291(4) . ?
N1 C5 1.475(15) . ?
N1 C3 1.477(16) . ?
N1 C1 1.511(12) . ?
N2 C2 1.487(14) . ?
N2 C4 1.513(15) . ?
N2 C7 1.521(14) . ?
N2 C6 1.526(16) . ?
C1 C2 1.558(16) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C3 C4 1.549(17) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C5 C6 1.532(17) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C7 C8 1.48(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?

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
Cl4 Co1 Cl1 107.03(12) . . ?
Cl4 Co1 Cl2 112.84(15) . . ?
Cl1 Co1 Cl2 112.25(14) . . ?
Cl4 Co1 Cl3 108.58(15) . . ?
Cl1 Co1 Cl3 115.60(13) . . ?
Cl2 Co1 Cl3 100.59(14) . . ?
C5 N1 C3 111.9(10) . . ?
C5 N1 C1 109.7(9) . . ?
C3 N1 C1 109.1(9) . . ?
C2 N2 C4 109.9(9) . . ?
C2 N2 C7 110.8(8) . . ?
C4 N2 C7 109.2(9) . . ?
C2 N2 C6 109.0(9) . . ?
C4 N2 C6 107.6(8) . . ?
C7 N2 C6 110.3(9) . . ?
N1 C1 C2 108.3(8) . . ?
N1 C1 H1A 110.0 . . ?
C2 C1 H1A 110.0 . . ?
N1 C1 H1B 110.0 . . ?
C2 C1 H1B 110.0 . . ?
H1A C1 H1B 108.4 . . ?
N2 C2 C1 109.8(8) . . ?
N2 C2 H2A 109.7 . . ?
C1 C2 H2A 109.7 . . ?
N2 C2 H2B 109.7 . . ?
C1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
N1 C3 C4 109.0(9) . . ?
N1 C3 H3A 109.9 . . ?
C4 C3 H3A 109.9 . . ?
N1 C3 H3B 109.9 . . ?
C4 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
N2 C4 C3 109.4(9) . . ?
N2 C4 H4A 109.8 . . ?
C3 C4 H4A 109.8 . . ?
N2 C4 H4B 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.2 . . ?
N1 C5 C6 109.2(10) . . ?
N1 C5 H5A 109.8 . . ?
C6 C5 H5A 109.8 . . ?
N1 C5 H5B 109.8 . . ?
C6 C5 H5B 109.8 . . ?
H5A C5 H5B 108.3 . . ?
N2 C6 C5 110.0(9) . . ?
N2 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C8 C7 N2 115.7(11) . . ?
C8 C7 H7A 108.4 . . ?
N2 C7 H7A 108.4 . . ?
C8 C7 H7B 108.4 . . ?
N2 C7 H7B 108.4 . . ?
H7A C7 H7B 107.4 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
C5 N1 C1 C2 64.4(12) . . . . ?
C3 N1 C1 C2 -58.6(12) . . . . ?
C4 N2 C2 C1 61.9(12) . . . . ?
C7 N2 C2 C1 -177.4(10) . . . . ?
C6 N2 C2 C1 -55.8(12) . . . . ?
N1 C1 C2 N2 -5.0(13) . . . . ?
C5 N1 C3 C4 -55.6(12) . . . . ?
C1 N1 C3 C4 65.9(12) . . . . ?
C2 N2 C4 C3 -54.9(12) . . . . ?
C7 N2 C4 C3 -176.6(9) . . . . ?
C6 N2 C4 C3 63.7(11) . . . . ?
N1 C3 C4 N2 -8.2(13) . . . . ?
C3 N1 C5 C6 62.6(13) . . . . ?
C1 N1 C5 C6 -58.6(13) . . . . ?
C2 N2 C6 C5 62.1(12) . . . . ?
C4 N2 C6 C5 -57.0(12) . . . . ?
C7 N2 C6 C5 -176.0(10) . . . . ?
N1 C5 C6 N2 -3.9(14) . . . . ?
C2 N2 C7 C8 68.9(14) . . . . ?
C4 N2 C7 C8 -169.9(11) . . . . ?
C6 N2 C7 C8 -51.9(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_theta_full        25.51
_diffrn_measured_fraction_theta_full 0.964
_refine_diff_density_max         2.273
_refine_diff_density_min         -0.966
_refine_diff_density_rms         0.243
####################################################################### 
# 
# 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_111_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1476565'
_audit_update_record             
;
2016-04-26 deposited with the CCDC.
2018-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H17 Cl4 Co N2'
_chemical_formula_weight         341.97

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'Pnma '

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

_cell_length_a                   11.2640(17)
_cell_length_b                   10.0243(16)
_cell_length_c                   12.4055(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1400.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4180
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      27.75

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    1.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6613
_exptl_absorpt_correction_T_max  0.7192
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9689
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.44
_diffrn_reflns_theta_max         28.02
_reflns_number_total             1774
_reflns_number_gt                1435
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0620P)²+1.8701P] 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         1774
_refine_ls_number_parameters     86
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1399
_refine_ls_wR_factor_gt          0.1289
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.140
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.28664(6) 0.2500 0.57700(5) 0.0369(2) Uani 1 2 d S . .
Cl2 Cl 0.39361(9) 0.07542(10) 0.64255(9) 0.0472(3) Uani 1 1 d . . .
Cl1 Cl 0.26852(14) 0.2500 0.39511(10) 0.0544(4) Uani 1 2 d S . .
Cl4 Cl 0.10194(13) 0.2500 0.64683(12) 0.0793(7) Uani 1 2 d S . .
N1 N 0.8198(4) 0.2500 0.4666(3) 0.0337(9) Uani 1 2 d S . .
C6 C 0.6010(5) 0.2500 0.4704(4) 0.0377(12) Uani 1 2 d S . .
H6A H 0.5533 0.3284 0.4555 0.045 Uiso 0.50 1 calc PR . .
H6B H 0.5533 0.1716 0.4555 0.045 Uiso 0.50 1 calc PR . .
C3 C 0.7099(4) 0.2500 0.3985(4) 0.0347(11) Uani 1 2 d S . .
H3A H 0.7091 0.1716 0.3527 0.042 Uiso 0.50 1 calc PR . .
H3B H 0.7091 0.3284 0.3527 0.042 Uiso 0.50 1 calc PR . .
C4 C 0.8191(4) 0.1287(4) 0.5375(3) 0.0411(9) Uani 1 1 d . . .
H4A H 0.8892 0.1288 0.5829 0.049 Uiso 1 1 calc R . .
H4B H 0.8211 0.0490 0.4932 0.049 Uiso 1 1 calc R . .
C5 C 0.7087(4) 0.1273(5) 0.6076(3) 0.0487(10) Uani 1 1 d . . .
H5A H 0.6616 0.0487 0.5917 0.058 Uiso 1 1 calc R . .
H5B H 0.7311 0.1243 0.6830 0.058 Uiso 1 1 calc R . .
N6 N 0.6376(4) 0.2500 0.5858(3) 0.0373(10) Uani 1 2 d S . .
C2 C 0.9301(5) 0.2500 0.3969(5) 0.0565(17) Uani 1 2 d S . .
H2A H 0.9975 0.2500 0.4440 0.068 Uiso 1 2 d SR . .
H2B H 0.9287 0.3293 0.3536 0.068 Uiso 0.50 1 d PR . .
C1 C 0.9505(9) 0.1403(12) 0.3276(8) 0.067(3) Uani 0.50 1 d P . .
H1A H 0.8812 0.1250 0.2842 0.100 Uiso 0.50 1 calc PR . .
H1B H 0.9670 0.0622 0.3698 0.100 Uiso 0.50 1 calc PR . .
H1C H 1.0170 0.1592 0.2817 0.100 Uiso 0.50 1 calc PR . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Co1 0.0374(4) 0.0432(4) 0.0302(4) 0.000 0.0004(3) 0.000
Cl2 0.0534(6) 0.0311(5) 0.0571(6) -0.0003(4) -0.0013(5) 0.0014(4)
Cl1 0.0586(9) 0.0840(12) 0.0206(6) 0.000 -0.0007(6) 0.000
Cl4 0.0329(7) 0.170(2) 0.0346(8) 0.000 -0.0024(6) 0.000
N1 0.031(2) 0.040(2) 0.030(2) 0.000 -0.0018(17) 0.000
C6 0.036(3) 0.044(3) 0.033(3) 0.000 -0.005(2) 0.000
C3 0.037(3) 0.041(3) 0.026(2) 0.000 -0.006(2) 0.000
C4 0.046(2) 0.039(2) 0.0384(19) 0.0067(17) -0.0026(16) 0.0073(17)
C5 0.054(2) 0.052(3) 0.040(2) 0.0167(19) 0.0041(18) 0.010(2)
N6 0.040(2) 0.042(2) 0.030(2) 0.000 0.0001(18) 0.000
C2 0.036(3) 0.090(5) 0.043(3) 0.000 0.008(3) 0.000
C1 0.058(5) 0.086(8) 0.055(5) -0.019(5) 0.008(5) 0.024(5)

_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
Co1 Cl4 2.2535(17) . ?
Co1 Cl1 2.2656(15) . ?
Co1 Cl2 2.2750(11) 8_565 ?
Co1 Cl2 2.2750(11) . ?
N1 C3 1.499(6) . ?
N1 C4 1.501(4) . ?
N1 C4 1.501(4) 8_565 ?
N1 C2 1.514(7) . ?
C6 N6 1.489(6) . ?
C6 C3 1.516(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.517(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 N6 1.492(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
N6 C5 1.492(5) 8_565 ?
C2 C1 1.415(10) . ?
C2 C1 1.415(10) 8_565 ?
C2 H2A 0.9576 . ?
C2 H2B 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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
Cl4 Co1 Cl1 107.44(6) . . ?
Cl4 Co1 Cl2 110.58(4) . 8_565 ?
Cl1 Co1 Cl2 113.81(4) . 8_565 ?
Cl4 Co1 Cl2 110.58(4) . . ?
Cl1 Co1 Cl2 113.81(4) . . ?
Cl2 Co1 Cl2 100.57(6) 8_565 . ?
C3 N1 C4 109.0(3) . . ?
C3 N1 C4 109.0(3) . 8_565 ?
C4 N1 C4 108.2(4) . 8_565 ?
C3 N1 C2 110.9(4) . . ?
C4 N1 C2 109.8(3) . . ?
C4 N1 C2 109.8(3) 8_565 . ?
N6 C6 C3 110.0(4) . . ?
N6 C6 H6A 109.7 . . ?
C3 C6 H6A 109.7 . . ?
N6 C6 H6B 109.7 . . ?
C3 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N1 C3 C6 109.7(4) . . ?
N1 C3 H3A 109.7 . . ?
C6 C3 H3A 109.7 . . ?
N1 C3 H3B 109.7 . . ?
C6 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
N1 C4 C5 110.3(3) . . ?
N1 C4 H4A 109.6 . . ?
C5 C4 H4A 109.6 . . ?
N1 C4 H4B 109.6 . . ?
C5 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
N6 C5 C4 109.2(3) . . ?
N6 C5 H5A 109.8 . . ?
C4 C5 H5A 109.8 . . ?
N6 C5 H5B 109.8 . . ?
C4 C5 H5B 109.8 . . ?
H5A C5 H5B 108.3 . . ?
C6 N6 C5 108.8(3) . 8_565 ?
C6 N6 C5 108.8(3) . . ?
C5 N6 C5 111.1(5) 8_565 . ?
C1 C2 C1 102.0(10) . 8_565 ?
C1 C2 N1 118.7(6) . . ?
C1 C2 N1 118.7(6) 8_565 . ?
C1 C2 H2A 104.0 . . ?
C1 C2 H2A 104.0 8_565 . ?
N1 C2 H2A 107.6 . . ?
C1 C2 H2B 107.8 . . ?
C1 C2 H2B 11.0 8_565 . ?
N1 C2 H2B 107.8 . . ?
H2A C2 H2B 110.8 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
C4 N1 C3 C6 59.0(3) . . . . ?
C4 N1 C3 C6 -59.0(3) 8_565 . . . ?
C2 N1 C3 C6 180.0 . . . . ?
N6 C6 C3 N1 0.0 . . . . ?
C3 N1 C4 C5 -58.1(4) . . . . ?
C4 N1 C4 C5 60.3(5) 8_565 . . . ?
C2 N1 C4 C5 -179.8(4) . . . . ?
N1 C4 C5 N6 -1.8(5) . . . . ?
C3 C6 N6 C5 60.6(3) . . . 8_565 ?
C3 C6 N6 C5 -60.6(3) . . . . ?
C4 C5 N6 C6 61.3(4) . . . . ?
C4 C5 N6 C5 -58.4(5) . . . 8_565 ?
C3 N1 C2 C1 -62.4(7) . . . . ?
C4 N1 C2 C1 58.2(8) . . . . ?
C4 N1 C2 C1 177.1(6) 8_565 . . . ?
C3 N1 C2 C1 62.4(7) . . . 8_565 ?
C4 N1 C2 C1 -177.1(6) . . . 8_565 ?
C4 N1 C2 C1 -58.2(8) 8_565 . . 8_565 ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        28.02
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.812
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.099
