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

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

data_fb-co-354-2
_database_code_depnum_ccdc_archive 'CCDC 1470079'
_audit_update_record             
;
2016-03-22 deposited with the CCDC.
2016-05-24 downloaded from the CCDC.
;

_chemical_formula_moiety         'C6 H5 Cl3 Co N3, C6 H6 N3'
_chemical_formula_sum            'C12 H11 Cl3 Co N6'
_chemical_formula_weight         404.90
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7169(13)
_cell_length_b                   9.6741(19)
_cell_length_c                   12.513(3)
_cell_angle_alpha                94.91(3)
_cell_angle_beta                 103.38(3)
_cell_angle_gamma                94.97(3)
_cell_volume                     783.4(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4746
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.259
_cell_measurement_theta_min      2.854
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.612
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6936
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'Sadabs 2014/3 (Bruker 2014)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             406
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10117
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.291
_diffrn_reflns_theta_min         1.683
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_source                   'rotating anode'
_diffrn_radiation_monochromator  helios
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3418
_reflns_number_total             3868
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 ver. 2014.1 (Bruker AXS)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'Olex2 (Dolomanov et al., 2009)'
_refine_diff_density_max         1.765
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         3868
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0328P)²+1.2129P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0888
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(Cl3) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
3.a Aromatic/amide H refined with riding coordinates:
 N6(H6), C5(H5), C4(H4), C8(H8), C2(H2), C3(H3A), C9(H9), C11(H11), C10(H10)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Co1 Co 0.30143(5) 0.69324(3) 0.75199(3) 0.01356(9) Uani 1 1 d . . . . .
Cl2 Cl 0.53960(10) 0.82505(6) 0.88973(4) 0.02146(14) Uani 1 1 d . . . . .
Cl1 Cl 0.41448(11) 0.68501(7) 0.59505(5) 0.02588(15) Uani 1 1 d . . . . .
N1 N 0.2985(3) 0.49450(19) 0.78934(15) 0.0109(3) Uani 1 1 d . . . . .
N6 N 0.2873(3) 0.9972(2) 0.28389(15) 0.0130(4) Uani 1 1 d . . . . .
H6 H 0.2826 1.0792 0.2584 0.016 Uiso 1 1 calc R . . . .
N3 N 0.3372(3) 0.3383(2) 0.90079(16) 0.0129(4) Uani 1 1 d . . . . .
N2 N 0.3475(3) 0.47538(19) 0.89432(15) 0.0124(4) Uani 1 1 d . . . . .
N4 N 0.3260(3) 0.8458(2) 0.39345(17) 0.0141(4) Uani 1 1 d . . . . .
N5 N 0.3362(3) 0.9812(2) 0.38944(16) 0.0151(4) Uani 1 1 d . . . . .
C6 C 0.2548(3) 0.3673(2) 0.72613(18) 0.0105(4) Uani 1 1 d . . . . .
C7 C 0.2445(3) 0.8736(2) 0.21793(18) 0.0120(4) Uani 1 1 d . . . . .
C1 C 0.2800(3) 0.2650(2) 0.79884(18) 0.0110(4) Uani 1 1 d . . . . .
C12 C 0.2701(3) 0.7722(2) 0.29144(18) 0.0126(4) Uani 1 1 d . . . . .
C5 C 0.1978(3) 0.3323(2) 0.61113(18) 0.0140(4) Uani 1 1 d . . . . .
H5 H 0.1805 0.4014 0.5612 0.017 Uiso 1 1 calc R . . . .
C4 C 0.1683(4) 0.1920(3) 0.5748(2) 0.0176(5) Uani 1 1 d . . . . .
H4 H 0.1299 0.1635 0.4976 0.021 Uiso 1 1 calc R . . . .
C8 C 0.1885(4) 0.8391(3) 0.10307(19) 0.0178(5) Uani 1 1 d . . . . .
H8 H 0.1708 0.9079 0.0529 0.021 Uiso 1 1 calc R . . . .
C2 C 0.2495(3) 0.1219(2) 0.7620(2) 0.0156(4) Uani 1 1 d . . . . .
H2 H 0.2664 0.0525 0.8117 0.019 Uiso 1 1 calc R . . . .
C3 C 0.1935(4) 0.0885(2) 0.6495(2) 0.0187(5) Uani 1 1 d . . . . .
H3A H 0.1709 -0.0071 0.6205 0.022 Uiso 1 1 calc R . . . .
C9 C 0.1611(4) 0.6986(3) 0.0682(2) 0.0217(5) Uani 1 1 d . . . . .
H9 H 0.1233 0.6693 -0.0089 0.026 Uiso 1 1 calc R . . . .
C11 C 0.2410(3) 0.6288(2) 0.2554(2) 0.0179(5) Uani 1 1 d . . . . .
H11 H 0.2575 0.5596 0.3053 0.021 Uiso 1 1 calc R . . . .
C10 C 0.1870(4) 0.5957(3) 0.1429(2) 0.0226(5) Uani 1 1 d . . . . .
H10 H 0.1661 0.5001 0.1139 0.027 Uiso 1 1 calc R . . . .
H3 H 0.376(5) 0.309(4) 0.965(3) 0.034(9) Uiso 1 1 d . . . . .
H4A H 0.352(5) 0.814(4) 0.454(3) 0.033(9) Uiso 1 1 d . . . . .
Cl3 Cl -0.01664(11) 0.74722(8) 0.74232(8) 0.0442(2) Uani 1 1 d . 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
Co1 Cl2 2.2693(12) . ?
Co1 Cl1 2.2614(8) . ?
Co1 N1 2.0167(19) . ?
Co1 Cl3 2.2218(9) . ?
N1 N2 1.312(3) . ?
N1 C6 1.374(3) . ?
N6 H6 0.8800 . ?
N6 N5 1.311(3) . ?
N6 C7 1.362(3) . ?
N3 N2 1.332(3) . ?
N3 C1 1.360(3) . ?
N3 H3 0.86(3) . ?
N4 N5 1.311(3) . ?
N4 C12 1.361(3) . ?
N4 H4A 0.83(3) . ?
C6 C1 1.396(3) . ?
C6 C5 1.404(3) . ?
C7 C12 1.396(3) . ?
C7 C8 1.402(3) . ?
C1 C2 1.403(3) . ?
C12 C11 1.404(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.376(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.421(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.375(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.372(3) . ?
C3 H3A 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.417(4) . ?
C11 H11 0.9500 . ?
C11 C10 1.372(4) . ?
C10 H10 0.9500 . ?

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
Cl1 Co1 Cl2 109.28(3) . . ?
N1 Co1 Cl2 107.05(6) . . ?
N1 Co1 Cl1 103.50(6) . . ?
N1 Co1 Cl3 105.32(6) . . ?
Cl3 Co1 Cl2 112.92(4) . . ?
Cl3 Co1 Cl1 117.73(4) . . ?
N2 N1 Co1 117.26(14) . . ?
N2 N1 C6 109.52(18) . . ?
C6 N1 Co1 133.22(15) . . ?
N5 N6 H6 123.6 . . ?
N5 N6 C7 112.86(19) . . ?
C7 N6 H6 123.6 . . ?
N2 N3 C1 111.44(18) . . ?
N2 N3 H3 118(2) . . ?
C1 N3 H3 130(2) . . ?
N1 N2 N3 107.69(18) . . ?
N5 N4 C12 112.77(19) . . ?
N5 N4 H4A 120(2) . . ?
C12 N4 H4A 128(2) . . ?
N4 N5 N6 105.16(18) . . ?
N1 C6 C1 107.07(19) . . ?
N1 C6 C5 131.4(2) . . ?
C1 C6 C5 121.5(2) . . ?
N6 C7 C12 104.52(19) . . ?
N6 C7 C8 133.3(2) . . ?
C12 C7 C8 122.2(2) . . ?
N3 C1 C6 104.29(19) . . ?
N3 C1 C2 133.3(2) . . ?
C6 C1 C2 122.4(2) . . ?
N4 C12 C7 104.70(19) . . ?
N4 C12 C11 133.0(2) . . ?
C7 C12 C11 122.3(2) . . ?
C6 C5 H5 121.9 . . ?
C4 C5 C6 116.2(2) . . ?
C4 C5 H5 121.9 . . ?
C5 C4 H4 119.1 . . ?
C5 C4 C3 121.9(2) . . ?
C3 C4 H4 119.1 . . ?
C7 C8 H8 122.4 . . ?
C9 C8 C7 115.2(2) . . ?
C9 C8 H8 122.4 . . ?
C1 C2 H2 122.1 . . ?
C3 C2 C1 115.7(2) . . ?
C3 C2 H2 122.1 . . ?
C4 C3 H3A 118.9 . . ?
C2 C3 C4 122.3(2) . . ?
C2 C3 H3A 118.9 . . ?
C8 C9 H9 118.8 . . ?
C8 C9 C10 122.5(2) . . ?
C10 C9 H9 118.8 . . ?
C12 C11 H11 122.4 . . ?
C10 C11 C12 115.2(2) . . ?
C10 C11 H11 122.4 . . ?
C9 C10 H10 118.7 . . ?
C11 C10 C9 122.6(2) . . ?
C11 C10 H10 118.7 . . ?

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
Co1 N1 N2 N3 -179.65(13) . . . . ?
Co1 N1 C6 C1 179.70(15) . . . . ?
Co1 N1 C6 C5 0.6(4) . . . . ?
N1 C6 C1 N3 0.0(2) . . . . ?
N1 C6 C1 C2 -179.39(19) . . . . ?
N1 C6 C5 C4 179.0(2) . . . . ?
N6 C7 C12 N4 -0.2(2) . . . . ?
N6 C7 C12 C11 -179.6(2) . . . . ?
N6 C7 C8 C9 179.1(2) . . . . ?
N3 C1 C2 C3 -179.0(2) . . . . ?
N2 N1 C6 C1 -0.1(2) . . . . ?
N2 N1 C6 C5 -179.2(2) . . . . ?
N2 N3 C1 C6 0.1(2) . . . . ?
N2 N3 C1 C2 179.4(2) . . . . ?
N4 C12 C11 C10 -178.8(2) . . . . ?
N5 N6 C7 C12 0.1(2) . . . . ?
N5 N6 C7 C8 -179.3(2) . . . . ?
N5 N4 C12 C7 0.2(2) . . . . ?
N5 N4 C12 C11 179.6(2) . . . . ?
C6 N1 N2 N3 0.2(2) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
C6 C5 C4 C3 0.2(3) . . . . ?
C7 N6 N5 N4 0.1(2) . . . . ?
C7 C12 C11 C10 0.4(3) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
C1 N3 N2 N1 -0.2(2) . . . . ?
C1 C6 C5 C4 0.0(3) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C12 N4 N5 N6 -0.2(2) . . . . ?
C12 C7 C8 C9 -0.1(3) . . . . ?
C12 C11 C10 C9 -0.4(3) . . . . ?
C5 C6 C1 N3 179.15(19) . . . . ?
C5 C6 C1 C2 -0.2(3) . . . . ?
C5 C4 C3 C2 -0.3(4) . . . . ?
C8 C7 C12 N4 179.2(2) . . . . ?
C8 C7 C12 C11 -0.2(3) . . . . ?
C8 C9 C10 C11 0.1(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_fb-co-371-2blau
_database_code_depnum_ccdc_archive 'CCDC 1470080'
_audit_update_record             
;
2016-03-22 deposited with the CCDC.
2016-05-24 downloaded from the CCDC.
;


_chemical_formula_moiety         'C12 H10 Cl2 Co N6'
_chemical_formula_sum            'C12 H10 Cl2 Co N6'
_chemical_formula_weight         368.09
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   7.560(4)
_cell_length_b                   13.9232(9)
_cell_length_c                   13.849(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.069(2)
_cell_angle_gamma                90
_cell_volume                     1456.8(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5089
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.394
_cell_measurement_theta_min      2.926
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.545
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6687
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'Sadabs 2014/3 (Bruker 2014)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             740
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21969
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.306
_diffrn_reflns_theta_min         2.075
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_source                   'rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2940
_reflns_number_total             3621
_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.
;

_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'APEX2 ver. 2014.1 (Bruker AXS)'
_computing_cell_refinement       'Saint-NT v. 7.23'
_computing_data_reduction        'Saint-NT v. 7.23'
_computing_structure_solution    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3621
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0319
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0275P)²+1.1161P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0736
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N6(H6), N3(H3), C5(H5), C8(H8), C10(H10), C11(H11), C3(H3A), C4(H4), C2(H2),
 C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Co1 Co 0.24900(4) 0.57342(2) 0.27697(2) 0.01256(8) Uani 1 1 d . . . . .
Cl2 Cl 0.52708(7) 0.51573(4) 0.27923(4) 0.01768(12) Uani 1 1 d . . . . .
Cl1 Cl 0.03738(7) 0.46315(4) 0.24647(4) 0.01566(12) Uani 1 1 d . . . . .
N5 N 0.1381(3) 0.56287(13) 0.46862(13) 0.0165(4) Uani 1 1 d . . . . .
N1 N 0.2151(2) 0.68175(13) 0.18326(12) 0.0139(4) Uani 1 1 d . . . . .
N6 N 0.1249(2) 0.60412(13) 0.55459(13) 0.0158(4) Uani 1 1 d . . . . .
H6 H 0.0814 0.5765 0.6039 0.019 Uiso 1 1 calc R . . . .
N4 N 0.2107(2) 0.62565(13) 0.41095(12) 0.0138(4) Uani 1 1 d . . . . .
N2 N 0.1382(2) 0.76026(13) 0.21463(13) 0.0159(4) Uani 1 1 d . . . . .
N3 N 0.1279(2) 0.82204(13) 0.14157(13) 0.0163(4) Uani 1 1 d . . . . .
H3 H 0.0821 0.8784 0.1451 0.020 Uiso 1 1 calc R . . . .
C12 C 0.2452(3) 0.70934(15) 0.46086(15) 0.0133(4) Uani 1 1 d . . . . .
C5 C 0.3308(3) 0.63085(17) 0.02194(16) 0.0192(5) Uani 1 1 d . . . . .
H5 H 0.3663 0.5691 0.0394 0.023 Uiso 1 1 calc R . . . .
C7 C 0.1890(3) 0.69588(16) 0.55489(15) 0.0142(4) Uani 1 1 d . . . . .
C8 C 0.2017(3) 0.76775(17) 0.62538(16) 0.0188(5) Uani 1 1 d . . . . .
H8 H 0.1613 0.7586 0.6874 0.023 Uiso 1 1 calc R . . . .
C1 C 0.1987(3) 0.78524(15) 0.06027(15) 0.0142(4) Uani 1 1 d . . . . .
C10 C 0.3362(3) 0.86645(17) 0.50263(17) 0.0193(5) Uani 1 1 d . . . . .
H10 H 0.3869 0.9250 0.4871 0.023 Uiso 1 1 calc R . . . .
C11 C 0.3213(3) 0.79665(16) 0.43295(16) 0.0156(4) Uani 1 1 d . . . . .
H11 H 0.3595 0.8066 0.3706 0.019 Uiso 1 1 calc R . . . .
C6 C 0.2534(3) 0.69324(16) 0.08748(15) 0.0137(4) Uani 1 1 d . . . . .
C3 C 0.2984(3) 0.7603(2) -0.09586(17) 0.0262(6) Uani 1 1 d . . . . .
H3A H 0.3171 0.7814 -0.1584 0.031 Uiso 1 1 calc R . . . .
C4 C 0.3511(3) 0.66621(19) -0.06987(17) 0.0246(6) Uani 1 1 d . . . . .
H4 H 0.4010 0.6271 -0.1160 0.030 Uiso 1 1 calc R . . . .
C2 C 0.2211(3) 0.82136(18) -0.03297(16) 0.0220(5) Uani 1 1 d . . . . .
H2 H 0.1855 0.8830 -0.0508 0.026 Uiso 1 1 calc R . . . .
C9 C 0.2769(3) 0.85232(17) 0.59771(17) 0.0211(5) Uani 1 1 d . . . . .
H9 H 0.2896 0.9019 0.6424 0.025 Uiso 1 1 calc R . . . .


_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 Cl2 2.2495(12) . ?
Co1 Cl1 2.2464(8) . ?
Co1 N1 2.0003(18) . ?
Co1 N4 2.0236(18) . ?
N5 N6 1.329(2) . ?
N5 N4 1.317(2) . ?
N1 N2 1.319(2) . ?
N1 C6 1.377(3) . ?
N6 H6 0.8600 . ?
N6 C7 1.366(3) . ?
N4 C12 1.375(3) . ?
N2 N3 1.328(2) . ?
N3 H3 0.8600 . ?
N3 C1 1.364(3) . ?
C12 C7 1.397(3) . ?
C12 C11 1.405(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.399(3) . ?
C5 C4 1.377(3) . ?
C7 C8 1.399(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.369(3) . ?
C1 C6 1.394(3) . ?
C1 C2 1.402(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.371(3) . ?
C10 C9 1.420(3) . ?
C11 H11 0.9300 . ?
C3 H3A 0.9300 . ?
C3 C4 1.412(4) . ?
C3 C2 1.364(4) . ?
C4 H4 0.9300 . ?
C2 H2 0.9300 . ?
C9 H9 0.9300 . ?

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
Cl1 Co1 Cl2 114.67(3) . . ?
N1 Co1 Cl2 112.10(6) . . ?
N1 Co1 Cl1 108.64(6) . . ?
N1 Co1 N4 107.74(7) . . ?
N4 Co1 Cl2 106.28(6) . . ?
N4 Co1 Cl1 107.06(6) . . ?
N4 N5 N6 107.63(17) . . ?
N2 N1 Co1 117.31(13) . . ?
N2 N1 C6 109.37(17) . . ?
C6 N1 Co1 133.31(15) . . ?
N5 N6 H6 124.2 . . ?
N5 N6 C7 111.64(18) . . ?
C7 N6 H6 124.2 . . ?
N5 N4 Co1 113.22(13) . . ?
N5 N4 C12 109.47(17) . . ?
C12 N4 Co1 137.27(15) . . ?
N1 N2 N3 107.47(17) . . ?
N2 N3 H3 124.1 . . ?
N2 N3 C1 111.81(18) . . ?
C1 N3 H3 124.1 . . ?
N4 C12 C7 107.23(19) . . ?
N4 C12 C11 131.85(19) . . ?
C7 C12 C11 120.9(2) . . ?
C6 C5 H5 121.9 . . ?
C4 C5 H5 121.9 . . ?
C4 C5 C6 116.1(2) . . ?
N6 C7 C12 104.03(18) . . ?
N6 C7 C8 133.3(2) . . ?
C12 C7 C8 122.6(2) . . ?
C7 C8 H8 122.0 . . ?
C9 C8 C7 116.0(2) . . ?
C9 C8 H8 122.0 . . ?
N3 C1 C6 104.10(18) . . ?
N3 C1 C2 133.6(2) . . ?
C6 C1 C2 122.3(2) . . ?
C11 C10 H10 118.9 . . ?
C11 C10 C9 122.3(2) . . ?
C9 C10 H10 118.9 . . ?
C12 C11 H11 121.8 . . ?
C10 C11 C12 116.3(2) . . ?
C10 C11 H11 121.8 . . ?
N1 C6 C5 131.3(2) . . ?
N1 C6 C1 107.24(19) . . ?
C1 C6 C5 121.5(2) . . ?
C4 C3 H3A 118.7 . . ?
C2 C3 H3A 118.7 . . ?
C2 C3 C4 122.6(2) . . ?
C5 C4 C3 121.8(2) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C1 C2 H2 122.2 . . ?
C3 C2 C1 115.7(2) . . ?
C3 C2 H2 122.2 . . ?
C8 C9 C10 121.8(2) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?

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
Co1 N1 N2 N3 -179.61(13) . . . . ?
Co1 N1 C6 C5 0.2(4) . . . . ?
Co1 N1 C6 C1 179.91(16) . . . . ?
Co1 N4 C12 C7 -177.49(16) . . . . ?
Co1 N4 C12 C11 2.4(4) . . . . ?
N5 N6 C7 C12 -0.2(2) . . . . ?
N5 N6 C7 C8 178.8(2) . . . . ?
N5 N4 C12 C7 -0.2(2) . . . . ?
N5 N4 C12 C11 179.7(2) . . . . ?
N1 N2 N3 C1 -0.2(2) . . . . ?
N6 N5 N4 Co1 178.06(13) . . . . ?
N6 N5 N4 C12 0.0(2) . . . . ?
N6 C7 C8 C9 179.6(2) . . . . ?
N4 N5 N6 C7 0.1(2) . . . . ?
N4 C12 C7 N6 0.2(2) . . . . ?
N4 C12 C7 C8 -178.9(2) . . . . ?
N4 C12 C11 C10 -180.0(2) . . . . ?
N2 N1 C6 C5 -178.6(2) . . . . ?
N2 N1 C6 C1 1.1(2) . . . . ?
N2 N3 C1 C6 0.8(2) . . . . ?
N2 N3 C1 C2 -179.2(2) . . . . ?
N3 C1 C6 N1 -1.1(2) . . . . ?
N3 C1 C6 C5 178.6(2) . . . . ?
N3 C1 C2 C3 -179.4(2) . . . . ?
C12 C7 C8 C9 -1.5(3) . . . . ?
C7 C12 C11 C10 -0.1(3) . . . . ?
C7 C8 C9 C10 0.8(3) . . . . ?
C11 C12 C7 N6 -179.7(2) . . . . ?
C11 C12 C7 C8 1.2(3) . . . . ?
C11 C10 C9 C8 0.2(4) . . . . ?
C6 N1 N2 N3 -0.6(2) . . . . ?
C6 C5 C4 C3 0.6(3) . . . . ?
C6 C1 C2 C3 0.6(3) . . . . ?
C4 C5 C6 N1 -179.6(2) . . . . ?
C4 C5 C6 C1 0.8(3) . . . . ?
C4 C3 C2 C1 0.7(3) . . . . ?
C2 C1 C6 N1 178.88(19) . . . . ?
C2 C1 C6 C5 -1.4(3) . . . . ?
C2 C3 C4 C5 -1.4(4) . . . . ?
C9 C10 C11 C12 -0.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_fb-co-371-2rosa
_database_code_depnum_ccdc_archive 'CCDC 1470081'
_audit_update_record             
;
2016-03-22 deposited with the CCDC.
2016-05-24 downloaded from the CCDC.
;
_audit_creation_date             2015-09-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H20 Cl2 Co N12, 4(C6 H5 N3)'
_chemical_formula_sum            'C48 H40 Cl2 Co N24'
_chemical_formula_weight         1082.87
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 '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'

_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.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           85
_space_group_name_H-M_alt        'P 4/n'
_space_group_name_Hall           '-P 4a'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+1/2, x, z'
'-x+1/2, -y+1/2, z'
'y, -x+1/2, z'
'-x, -y, -z'
'y-1/2, -x, -z'
'x-1/2, y-1/2, -z'
'-y, x-1/2, -z'

_cell_length_a                   16.2192(16)
_cell_length_b                   16.2192(16)
_cell_length_c                   8.8865(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2337.7(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9943
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.063
_cell_measurement_theta_min      2.292
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.549
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6420
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'Sadabs 2014/3 (Bruker 2014)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1114
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            31501
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.128
_diffrn_reflns_theta_min         1.776
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_source                   'rotating anode'
_diffrn_radiation_monochromator  helios
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2245
_reflns_number_total             2594
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 ver. 2014.1 (Bruker AXS)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'Olex2 (Dolomanov et al., 2009)'
_refine_diff_density_max         0.619
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2594
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0294
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0354P)²+1.7440P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0745
_refine_ls_wR_factor_ref         0.0790
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C4(H4), C2(H2), C5(H5), C3(H3A), N6(H6), C9(H9), C11(H11), C10(H10),
 C8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Co1 Co 0.2500 0.2500 0.60793(5) 0.01059(11) Uani 1 4 d S T P . .
Cl1 Cl 0.2500 0.2500 0.30352(8) 0.01367(16) Uani 1 4 d S T P . .
Cl2 Cl 0.2500 0.2500 0.88228(8) 0.01361(16) Uani 1 4 d S T P . .
N1 N 0.32413(8) 0.36090(7) 0.59820(14) 0.0114(3) Uani 1 1 d . . . . .
N3 N 0.42296(8) 0.44048(8) 0.66696(15) 0.0135(3) Uani 1 1 d . . . . .
H3 H 0.4665 0.4573 0.7128 0.016 Uiso 1 1 calc R . . . .
C1 C 0.37946(9) 0.48606(9) 0.56639(17) 0.0128(3) Uani 1 1 d . . . . .
C6 C 0.31528(9) 0.43442(9) 0.52150(17) 0.0114(3) Uani 1 1 d . . . . .
N2 N 0.38918(8) 0.36607(8) 0.68533(15) 0.0134(3) Uani 1 1 d . . . . .
C4 C 0.26513(10) 0.54054(10) 0.36345(18) 0.0176(3) Uani 1 1 d . . . . .
H4 H 0.2274 0.5604 0.2935 0.021 Uiso 1 1 calc R . . . .
C2 C 0.38843(10) 0.56685(10) 0.51265(19) 0.0170(3) Uani 1 1 d . . . . .
H2 H 0.4314 0.6008 0.5437 0.020 Uiso 1 1 calc R . . . .
C5 C 0.25625(9) 0.46144(10) 0.41701(17) 0.0138(3) Uani 1 1 d . . . . .
H5 H 0.2133 0.4276 0.3856 0.017 Uiso 1 1 calc R . . . .
C3 C 0.33013(11) 0.59263(10) 0.41169(19) 0.0195(3) Uani 1 1 d . . . . .
H3A H 0.3333 0.6459 0.3736 0.023 Uiso 1 1 calc R . . . .
N5 N 0.42349(8) 0.41999(9) 0.20093(16) 0.0183(3) Uani 1 1 d . . . . .
N6 N 0.35810(8) 0.39531(8) 0.11897(15) 0.0157(3) Uani 1 1 d . . . . .
H6 H 0.3354 0.3476 0.1259 0.019 Uiso 1 1 calc R . . . .
C12 C 0.38825(9) 0.51998(10) 0.05093(17) 0.0136(3) Uani 1 1 d . . . . .
C7 C 0.33277(9) 0.45609(9) 0.02367(17) 0.0128(3) Uani 1 1 d . . . . .
N4 N 0.44281(8) 0.49482(9) 0.16018(15) 0.0166(3) Uani 1 1 d . . . . .
C9 C 0.26358(10) 0.53566(10) -0.15735(18) 0.0165(3) Uani 1 1 d . . . . .
H9 H 0.2223 0.5424 -0.2289 0.020 Uiso 1 1 calc R . . . .
C11 C 0.38156(10) 0.59507(10) -0.02738(18) 0.0177(3) Uani 1 1 d . . . . .
H11 H 0.4182 0.6382 -0.0106 0.021 Uiso 1 1 calc R . . . .
C10 C 0.31866(10) 0.60167(10) -0.12950(18) 0.0183(3) Uani 1 1 d . . . . .
H10 H 0.3119 0.6508 -0.1820 0.022 Uiso 1 1 calc R . . . .
C8 C 0.26927(9) 0.46197(10) -0.08206(17) 0.0144(3) Uani 1 1 d . . . . .
H8 H 0.2331 0.4186 -0.1003 0.017 Uiso 1 1 calc R . . . .


_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 Cl1 2.7052(9) . ?
Co1 Cl2 2.4380(9) . ?
Co1 N1 2.1653(12) 2 ?
Co1 N1 2.1653(12) 4 ?
Co1 N1 2.1653(12) . ?
Co1 N1 2.1653(12) 3 ?
N1 C6 1.3809(19) . ?
N1 N2 1.3114(18) . ?
N3 H3 0.8600 . ?
N3 C1 1.358(2) . ?
N3 N2 1.3355(18) . ?
C1 C6 1.394(2) . ?
C1 C2 1.402(2) . ?
C6 C5 1.404(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.376(2) . ?
C4 C3 1.417(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.369(2) . ?
C5 H5 0.9300 . ?
C3 H3A 0.9300 . ?
N5 N6 1.3474(19) . ?
N5 N4 1.3047(19) . ?
N6 H6 0.8600 . ?
N6 C7 1.363(2) . ?
C12 C7 1.394(2) . ?
C12 N4 1.376(2) . ?
C12 C11 1.407(2) . ?
C7 C8 1.397(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.416(2) . ?
C9 C8 1.373(2) . ?
C11 H11 0.9300 . ?
C11 C10 1.370(2) . ?
C10 H10 0.9300 . ?
C8 H8 0.9300 . ?

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
Cl2 Co1 Cl1 180.0 . . ?
N1 Co1 Cl1 87.71(3) 2 . ?
N1 Co1 Cl1 87.71(3) . . ?
N1 Co1 Cl1 87.71(3) 4 . ?
N1 Co1 Cl1 87.71(3) 3 . ?
N1 Co1 Cl2 92.29(3) . . ?
N1 Co1 Cl2 92.29(3) 4 . ?
N1 Co1 Cl2 92.29(3) 3 . ?
N1 Co1 Cl2 92.29(3) 2 . ?
N1 Co1 N1 175.42(7) 4 2 ?
N1 Co1 N1 89.908(3) 3 2 ?
N1 Co1 N1 89.908(3) 3 4 ?
N1 Co1 N1 175.42(7) 3 . ?
N1 Co1 N1 89.907(3) 4 . ?
N1 Co1 N1 89.910(3) 2 . ?
C6 N1 Co1 132.79(10) . . ?
N2 N1 Co1 118.44(9) . . ?
N2 N1 C6 108.65(12) . . ?
C1 N3 H3 124.5 . . ?
N2 N3 H3 124.5 . . ?
N2 N3 C1 111.06(12) . . ?
N3 C1 C6 104.44(13) . . ?
N3 C1 C2 132.77(15) . . ?
C6 C1 C2 122.78(14) . . ?
N1 C6 C1 107.45(13) . . ?
N1 C6 C5 131.82(14) . . ?
C1 C6 C5 120.72(14) . . ?
N1 N2 N3 108.40(12) . . ?
C5 C4 H4 119.0 . . ?
C5 C4 C3 121.94(15) . . ?
C3 C4 H4 119.0 . . ?
C1 C2 H2 122.0 . . ?
C3 C2 C1 115.90(15) . . ?
C3 C2 H2 122.0 . . ?
C6 C5 H5 121.7 . . ?
C4 C5 C6 116.64(14) . . ?
C4 C5 H5 121.7 . . ?
C4 C3 H3A 119.0 . . ?
C2 C3 C4 122.01(15) . . ?
C2 C3 H3A 119.0 . . ?
N4 N5 N6 108.38(13) . . ?
N5 N6 H6 124.5 . . ?
N5 N6 C7 110.99(13) . . ?
C7 N6 H6 124.5 . . ?
C7 C12 C11 120.53(14) . . ?
N4 C12 C7 108.50(14) . . ?
N4 C12 C11 130.96(14) . . ?
N6 C7 C12 103.60(13) . . ?
N6 C7 C8 133.57(14) . . ?
C12 C7 C8 122.82(14) . . ?
N5 N4 C12 108.51(13) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C8 C9 C10 122.04(15) . . ?
C12 C11 H11 121.5 . . ?
C10 C11 C12 116.92(14) . . ?
C10 C11 H11 121.5 . . ?
C9 C10 H10 119.1 . . ?
C11 C10 C9 121.78(15) . . ?
C11 C10 H10 119.1 . . ?
C7 C8 H8 122.1 . . ?
C9 C8 C7 115.89(14) . . ?
C9 C8 H8 122.1 . . ?

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
Co1 N1 C6 C1 176.01(10) . . . . ?
Co1 N1 C6 C5 -3.3(2) . . . . ?
Co1 N1 N2 N3 -176.86(9) . . . . ?
N1 C6 C5 C4 178.83(15) . . . . ?
N3 C1 C6 N1 0.09(16) . . . . ?
N3 C1 C6 C5 179.48(13) . . . . ?
N3 C1 C2 C3 -178.57(16) . . . . ?
C1 N3 N2 N1 0.35(17) . . . . ?
C1 C6 C5 C4 -0.4(2) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
C6 N1 N2 N3 -0.28(16) . . . . ?
C6 C1 C2 C3 -0.3(2) . . . . ?
N2 N1 C6 C1 0.12(16) . . . . ?
N2 N1 C6 C5 -179.18(15) . . . . ?
N2 N3 C1 C6 -0.27(17) . . . . ?
N2 N3 C1 C2 178.26(16) . . . . ?
C2 C1 C6 N1 -178.62(14) . . . . ?
C2 C1 C6 C5 0.8(2) . . . . ?
C5 C4 C3 C2 0.9(3) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
N5 N6 C7 C12 0.92(17) . . . . ?
N5 N6 C7 C8 -179.71(16) . . . . ?
N6 N5 N4 C12 0.85(17) . . . . ?
N6 C7 C8 C9 179.80(16) . . . . ?
C12 C7 C8 C9 -0.9(2) . . . . ?
C12 C11 C10 C9 -1.1(2) . . . . ?
C7 C12 N4 N5 -0.28(17) . . . . ?
C7 C12 C11 C10 0.1(2) . . . . ?
N4 N5 N6 C7 -1.14(17) . . . . ?
N4 C12 C7 N6 -0.39(17) . . . . ?
N4 C12 C7 C8 -179.84(14) . . . . ?
N4 C12 C11 C10 -178.93(16) . . . . ?
C11 C12 C7 N6 -179.63(14) . . . . ?
C11 C12 C7 C8 0.9(2) . . . . ?
C11 C12 N4 N5 178.85(16) . . . . ?
C10 C9 C8 C7 0.0(2) . . . . ?
C8 C9 C10 C11 1.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_fb-mn-226
_database_code_depnum_ccdc_archive 'CCDC 1470105'
_audit_update_record             
;
2016-03-22 deposited with the CCDC.
2016-05-24 downloaded from the CCDC.
;


_chemical_formula_moiety         'C12 H10 Cl2 Mn N6'
_chemical_formula_sum            'C12 H10 Cl2 Mn N6'
_chemical_formula_weight         364.10
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 '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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   16.4285(10)
_cell_length_b                   3.6906(2)
_cell_length_c                   23.2854(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1411.82(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5366
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.686
_cell_measurement_theta_min      2.629
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.314
_exptl_absorpt_correction_T_max  0.810
_exptl_absorpt_correction_T_min  0.741
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'Twinabs 2014/3 (Bruker 2014)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            19984
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.076
_diffrn_reflns_theta_min         1.749
_diffrn_ambient_temperature      99.65
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.956
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                3358
_reflns_number_total             3918
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 ver. 2014.1 (Bruker AXS)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'Olex2 (Dolomanov et al., 2009)'
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.090
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.06(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3918
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0345
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0411P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0789
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.94(3) 0.06(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C11(H11), C10(H10), N6(H6), C2(H2), C9(H9), C3(H3A), C8(H8), C4(H4),
 C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.62094(3) 0.41968(13) 0.35526(3) 0.00847(12) Uani 1 1 d . . . . .
Cl1 Cl 0.56229(5) -0.0788(2) 0.29178(3) 0.00971(19) Uani 1 1 d . . . . .
Cl2 Cl 0.67915(5) -0.0805(3) 0.41885(3) 0.00978(19) Uani 1 1 d . . . . .
N4 N 0.73633(19) 0.4329(9) 0.30091(14) 0.0093(6) Uani 1 1 d . . . . .
N5 N 0.8029(2) 0.5356(10) 0.32817(15) 0.0120(7) Uani 1 1 d . . . . .
N3 N 0.37782(18) 0.5548(10) 0.42147(15) 0.0124(7) Uani 1 1 d . . . . .
H3 H 0.3274 0.6153 0.4132 0.015 Uiso 1 1 calc R . . . .
C1 C 0.4041(2) 0.4579(11) 0.47457(18) 0.0097(7) Uani 1 1 d . . . . .
N2 N 0.4384(2) 0.5462(10) 0.38355(15) 0.0109(7) Uani 1 1 d . . . . .
C11 C 0.7111(2) 0.2258(12) 0.1984(2) 0.0121(10) Uani 1 1 d . . . . .
H11 H 0.6540 0.1902 0.2016 0.014 Uiso 1 1 calc R . . . .
C10 C 0.7520(3) 0.1656(13) 0.1475(2) 0.0148(9) Uani 1 1 d . . . . .
H10 H 0.7220 0.0909 0.1147 0.018 Uiso 1 1 calc R . . . .
N6 N 0.8657(2) 0.5129(9) 0.29170(16) 0.0112(7) Uani 1 1 d . . . . .
H6 H 0.9162 0.5693 0.3006 0.013 Uiso 1 1 calc R . . . .
C2 C 0.3651(2) 0.4326(11) 0.52848(17) 0.0139(8) Uani 1 1 d . . . . .
H2 H 0.3088 0.4822 0.5332 0.017 Uiso 1 1 calc R . . . .
C6 C 0.4875(2) 0.3845(10) 0.46693(17) 0.0097(7) Uani 1 1 d . . . . .
N1 N 0.50580(19) 0.4447(9) 0.40996(15) 0.0102(7) Uani 1 1 d . . . . .
C9 C 0.8374(3) 0.2122(11) 0.1429(2) 0.0138(9) Uani 1 1 d . . . . .
H9 H 0.8632 0.1648 0.1072 0.017 Uiso 1 1 calc R . . . .
C3 C 0.4135(3) 0.3325(12) 0.5733(2) 0.0146(9) Uani 1 1 d . . . . .
H3A H 0.3903 0.3126 0.6105 0.017 Uiso 1 1 calc R . . . .
C8 C 0.8836(2) 0.3236(11) 0.18842(18) 0.0130(8) Uani 1 1 d . . . . .
H8 H 0.9409 0.3523 0.1854 0.016 Uiso 1 1 calc R . . . .
C7 C 0.8419(2) 0.3930(10) 0.23964(17) 0.0093(8) Uani 1 1 d . . . . .
C12 C 0.7576(2) 0.3413(11) 0.24509(18) 0.0087(8) Uani 1 1 d . . . . .
C4 C 0.4976(3) 0.2572(11) 0.5659(2) 0.0143(9) Uani 1 1 d . . . . .
H4 H 0.5286 0.1889 0.5986 0.017 Uiso 1 1 calc R . . . .
C5 C 0.5359(3) 0.2786(11) 0.5138(2) 0.0130(10) Uani 1 1 d . . . . .
H5 H 0.5921 0.2248 0.5096 0.016 Uiso 1 1 calc R . . . .


_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 Cl1 2.5491(11) . ?
Mn1 Cl1 2.5572(11) 1_565 ?
Mn1 Cl2 2.5515(11) 1_565 ?
Mn1 Cl2 2.5522(11) . ?
Mn1 N4 2.280(3) . ?
Mn1 N1 2.282(3) . ?
Cl1 Mn1 2.5572(11) 1_545 ?
Cl2 Mn1 2.5514(11) 1_545 ?
N4 N5 1.319(5) . ?
N4 C12 1.388(5) . ?
N5 N6 1.339(5) . ?
N3 H3 0.8800 . ?
N3 C1 1.357(5) . ?
N3 N2 1.331(5) . ?
C1 C2 1.412(6) . ?
C1 C6 1.408(5) . ?
N2 N1 1.321(5) . ?
C11 H11 0.9500 . ?
C11 C10 1.380(7) . ?
C11 C12 1.395(6) . ?
C10 H10 0.9500 . ?
C10 C9 1.418(6) . ?
N6 H6 0.8800 . ?
N6 C7 1.348(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.363(6) . ?
C6 N1 1.379(5) . ?
C6 C5 1.407(6) . ?
C9 H9 0.9500 . ?
C9 C8 1.367(6) . ?
C3 H3A 0.9500 . ?
C3 C4 1.420(6) . ?
C8 H8 0.9500 . ?
C8 C7 1.399(6) . ?
C7 C12 1.403(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.368(7) . ?
C5 H5 0.9500 . ?

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
Cl1 Mn1 Cl1 92.56(3) . 1_565 ?
Cl1 Mn1 Cl2 179.80(4) . 1_565 ?
Cl1 Mn1 Cl2 87.48(3) . . ?
Cl2 Mn1 Cl1 179.82(4) . 1_565 ?
Cl2 Mn1 Cl1 87.33(3) 1_565 1_565 ?
Cl2 Mn1 Cl2 92.63(3) 1_565 . ?
N4 Mn1 Cl1 88.68(9) . 1_565 ?
N4 Mn1 Cl1 90.45(9) . . ?
N4 Mn1 Cl2 89.72(9) . 1_565 ?
N4 Mn1 Cl2 91.49(9) . . ?
N4 Mn1 N1 176.45(10) . . ?
N1 Mn1 Cl1 92.26(9) . . ?
N1 Mn1 Cl1 88.91(9) . 1_565 ?
N1 Mn1 Cl2 87.57(9) . 1_565 ?
N1 Mn1 Cl2 90.92(9) . . ?
Mn1 Cl1 Mn1 92.56(3) . 1_545 ?
Mn1 Cl2 Mn1 92.63(3) 1_545 . ?
N5 N4 Mn1 115.3(2) . . ?
N5 N4 C12 108.2(3) . . ?
C12 N4 Mn1 136.4(2) . . ?
N4 N5 N6 108.4(3) . . ?
C1 N3 H3 124.4 . . ?
N2 N3 H3 124.4 . . ?
N2 N3 C1 111.1(3) . . ?
N3 C1 C2 133.1(4) . . ?
N3 C1 C6 104.2(3) . . ?
C6 C1 C2 122.7(4) . . ?
N1 N2 N3 108.9(3) . . ?
C10 C11 H11 121.6 . . ?
C10 C11 C12 116.8(4) . . ?
C12 C11 H11 121.6 . . ?
C11 C10 H10 119.1 . . ?
C11 C10 C9 121.8(4) . . ?
C9 C10 H10 119.1 . . ?
N5 N6 H6 124.2 . . ?
N5 N6 C7 111.6(3) . . ?
C7 N6 H6 124.2 . . ?
C1 C2 H2 122.1 . . ?
C3 C2 C1 115.8(4) . . ?
C3 C2 H2 122.1 . . ?
N1 C6 C1 107.7(3) . . ?
N1 C6 C5 131.9(4) . . ?
C5 C6 C1 120.4(4) . . ?
N2 N1 Mn1 116.5(2) . . ?
N2 N1 C6 108.1(3) . . ?
C6 N1 Mn1 135.4(3) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 C10 121.8(4) . . ?
C8 C9 H9 119.1 . . ?
C2 C3 H3A 119.1 . . ?
C2 C3 C4 121.8(4) . . ?
C4 C3 H3A 119.1 . . ?
C9 C8 H8 121.8 . . ?
C9 C8 C7 116.3(4) . . ?
C7 C8 H8 121.8 . . ?
N6 C7 C8 133.2(4) . . ?
N6 C7 C12 104.4(3) . . ?
C8 C7 C12 122.4(4) . . ?
N4 C12 C11 131.7(4) . . ?
N4 C12 C7 107.5(3) . . ?
C11 C12 C7 120.8(4) . . ?
C3 C4 H4 118.5 . . ?
C5 C4 C3 122.9(4) . . ?
C5 C4 H4 118.5 . . ?
C6 C5 H5 121.8 . . ?
C4 C5 C6 116.4(4) . . ?
C4 C5 H5 121.8 . . ?

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
Mn1 N4 N5 N6 177.0(2) . . . . ?
Mn1 N4 C12 C11 5.8(7) . . . . ?
Mn1 N4 C12 C7 -175.8(3) . . . . ?
N4 N5 N6 C7 -0.3(4) . . . . ?
N5 N4 C12 C11 -178.2(5) . . . . ?
N5 N4 C12 C7 0.2(4) . . . . ?
N5 N6 C7 C8 -179.7(4) . . . . ?
N5 N6 C7 C12 0.4(4) . . . . ?
N3 C1 C2 C3 -178.2(4) . . . . ?
N3 C1 C6 N1 0.4(4) . . . . ?
N3 C1 C6 C5 179.2(4) . . . . ?
N3 N2 N1 Mn1 -178.6(3) . . . . ?
N3 N2 N1 C6 0.3(4) . . . . ?
C1 N3 N2 N1 0.0(5) . . . . ?
C1 C2 C3 C4 -0.3(6) . . . . ?
C1 C6 N1 Mn1 178.1(3) . . . . ?
C1 C6 N1 N2 -0.5(4) . . . . ?
C1 C6 C5 C4 -0.8(6) . . . . ?
N2 N3 C1 C2 178.3(4) . . . . ?
N2 N3 C1 C6 -0.3(4) . . . . ?
C11 C10 C9 C8 -0.8(7) . . . . ?
C10 C11 C12 N4 178.3(4) . . . . ?
C10 C11 C12 C7 0.1(6) . . . . ?
C10 C9 C8 C7 -0.7(6) . . . . ?
N6 C7 C12 N4 -0.4(4) . . . . ?
N6 C7 C12 C11 178.2(4) . . . . ?
C2 C1 C6 N1 -178.3(4) . . . . ?
C2 C1 C6 C5 0.4(6) . . . . ?
C2 C3 C4 C5 -0.1(7) . . . . ?
C6 C1 C2 C3 0.1(6) . . . . ?
N1 C6 C5 C4 177.6(4) . . . . ?
C9 C8 C7 N6 -178.0(4) . . . . ?
C9 C8 C7 C12 1.9(6) . . . . ?
C3 C4 C5 C6 0.6(6) . . . . ?
C8 C7 C12 N4 179.7(4) . . . . ?
C8 C7 C12 C11 -1.7(6) . . . . ?
C12 N4 N5 N6 0.1(4) . . . . ?
C12 C11 C10 C9 1.1(7) . . . . ?
C5 C6 N1 Mn1 -0.5(7) . . . . ?
C5 C6 N1 N2 -179.0(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.94(3)
2 0.06(3)

####################################################################### 
# 
# 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_test
_database_code_depnum_ccdc_archive 'CCDC 1471643'
_audit_update_record             
;
2016-03-31 deposited with the CCDC.
2016-05-24 downloaded from the CCDC.
;

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl, C12 H11 N6'
_chemical_formula_sum            'C12 H11 Cl N6'
_chemical_formula_weight         274.72
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   25.984(5)
_cell_length_b                   3.8567(8)
_cell_length_c                   14.587(3)
_cell_angle_alpha                90
_cell_angle_beta                 119.39(3)
_cell_angle_gamma                90
_cell_volume                     1273.6(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2626
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.113
_cell_measurement_theta_min      2.802
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.295
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0561 before and 0.0473 after correction.
The Ratio of minimum to maximum transmission is 0.8914.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.569
_exptl_crystal_size_mid          0.359
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7849
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.960
_diffrn_reflns_theta_min         1.799
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1202
_reflns_number_total             1403
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1403
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0329
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0335P)²+1.3917P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0822
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Others
 Fixed Sof: H3(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C5(H5), C3(H3A), C4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.5000 0.11823(13) 0.2500 0.01782(16) Uani 1 2 d S T P . .
N1 N 0.60559(6) 0.5501(3) 0.39757(10) 0.0184(3) Uani 1 1 d . . . . .
N3 N 0.69533(6) 0.7064(3) 0.48328(10) 0.0185(3) Uani 1 1 d . . . . .
H3 H 0.7317 0.7401 0.5007 0.022 Uiso 0.5 1 calc R . . . .
N2 N 0.65616(6) 0.5510(3) 0.39648(10) 0.0209(3) Uani 1 1 d . . . . .
C6 C 0.61094(6) 0.7040(4) 0.48571(11) 0.0157(3) Uani 1 1 d . . . . .
C1 C 0.66981(6) 0.8068(4) 0.54188(11) 0.0151(3) Uani 1 1 d . . . . .
C2 C 0.69266(7) 0.9744(4) 0.63944(12) 0.0192(3) Uani 1 1 d . . . . .
H2 H 0.7318 1.0473 0.6767 0.023 Uiso 1 1 calc R . . . .
C5 C 0.57133(7) 0.7630(4) 0.52322(13) 0.0222(4) Uani 1 1 d . . . . .
H5 H 0.5318 0.6990 0.4850 0.027 Uiso 1 1 calc R . . . .
C3 C 0.65396(8) 1.0244(4) 0.67660(13) 0.0241(4) Uani 1 1 d . . . . .
H3A H 0.6675 1.1304 0.7417 0.029 Uiso 1 1 calc R . . . .
C4 C 0.59428(8) 0.9204(4) 0.61943(13) 0.0263(4) Uani 1 1 d . . . . .
H4 H 0.5698 0.9601 0.6481 0.032 Uiso 1 1 calc R . . . .
H1 H 0.5735(9) 0.451(6) 0.3442(16) 0.042(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.3220(18) . ?
N1 C6 1.360(2) . ?
N1 H1 0.90(2) . ?
N3 H3 0.8600 . ?
N3 N2 1.3165(19) . ?
N3 C1 1.3699(19) . ?
C6 C1 1.392(2) . ?
C6 C5 1.401(2) . ?
C1 C2 1.402(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.370(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.368(2) . ?
C3 H3A 0.9300 . ?
C3 C4 1.411(2) . ?
C4 H4 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C6 111.67(13) . . ?
N2 N1 H1 119.7(13) . . ?
C6 N1 H1 128.6(13) . . ?
N2 N3 H3 124.9 . . ?
N2 N3 C1 110.27(12) . . ?
C1 N3 H3 124.9 . . ?
N3 N2 N1 107.06(12) . . ?
N1 C6 C1 104.70(13) . . ?
N1 C6 C5 133.33(15) . . ?
C1 C6 C5 121.97(14) . . ?
N3 C1 C6 106.30(13) . . ?
N3 C1 C2 132.08(14) . . ?
C6 C1 C2 121.61(13) . . ?
C1 C2 H2 122.0 . . ?
C3 C2 C1 116.04(14) . . ?
C3 C2 H2 122.0 . . ?
C6 C5 H5 122.0 . . ?
C4 C5 C6 116.02(15) . . ?
C4 C5 H5 122.0 . . ?
C2 C3 H3A 118.9 . . ?
C2 C3 C4 122.22(15) . . ?
C4 C3 H3A 118.9 . . ?
C5 C4 C3 122.11(15) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?

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
N1 C6 C1 N3 -0.08(16) . . . . ?
N1 C6 C1 C2 -179.30(14) . . . . ?
N1 C6 C5 C4 177.88(16) . . . . ?
N3 C1 C2 C3 -177.84(15) . . . . ?
N2 N1 C6 C1 0.23(17) . . . . ?
N2 N1 C6 C5 -179.19(16) . . . . ?
N2 N3 C1 C6 -0.10(16) . . . . ?
N2 N3 C1 C2 179.01(16) . . . . ?
C6 N1 N2 N3 -0.30(17) . . . . ?
C6 C1 C2 C3 1.2(2) . . . . ?
C6 C5 C4 C3 1.4(2) . . . . ?
C1 N3 N2 N1 0.25(16) . . . . ?
C1 C6 C5 C4 -1.5(2) . . . . ?
C1 C2 C3 C4 -1.3(2) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C5 C6 C1 N3 179.43(13) . . . . ?
C5 C6 C1 C2 0.2(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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 
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data_test
_database_code_depnum_ccdc_archive 'CCDC 1471652'
_audit_update_record             
;
2016-03-31 deposited with the CCDC.
2016-05-24 downloaded from the CCDC.
;
_audit_creation_date             2016-03-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 Cl2 N6 Zn, C6 H5 N3'
_chemical_formula_sum            'C18 H15 Cl2 N9 Zn'
_chemical_formula_weight         493.66
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   7.4412(10)
_cell_length_b                   38.081(5)
_cell_length_c                   7.5550(9)
_cell_angle_alpha                90
_cell_angle_beta                 101.859(5)
_cell_angle_gamma                90
_cell_volume                     2095.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3226
_cell_measurement_temperature    173
_cell_measurement_theta_max      25.89
_cell_measurement_theta_min      2.81
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.453
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.4995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1292 before and 0.0802 after correction.
The Ratio of minimum to maximum transmission is 0.6696.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.239
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.048
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1381
_diffrn_reflns_av_unetI/netI     0.1131
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       50
_diffrn_reflns_limit_k_min       -51
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            33720
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.190
_diffrn_reflns_theta_min         1.069
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3608
_reflns_number_total             5755
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.846
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         5755
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1008
_refine_ls_R_factor_gt           0.0484
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+1.9110P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.1171
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H7), C9(H8), C10(H9), C11(H10), N3(H1),
 N6(H6), C14(H12), C15(H13), C16(H14), C17(H15), N9(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0266(5) 0.52355(10) 0.1976(5) 0.0243(8) Uani 1 1 d . . . . .
C2 C -0.0837(6) 0.49034(10) 0.2454(5) 0.0330(9) Uani 1 1 d . . . . .
H2 H -0.2070 0.4840 0.2249 0.040 Uiso 1 1 calc R . . . .
C3 C 0.0529(6) 0.46795(10) 0.3239(5) 0.0371(11) Uani 1 1 d . . . . .
H3 H 0.0210 0.4457 0.3573 0.045 Uiso 1 1 calc R . . . .
C4 C 0.2405(6) 0.47723(10) 0.3565(5) 0.0334(9) Uani 1 1 d . . . . .
H4 H 0.3280 0.4610 0.4105 0.040 Uiso 1 1 calc R . . . .
C5 C 0.2969(5) 0.50973(9) 0.3103(5) 0.0260(8) Uani 1 1 d . . . . .
H5 H 0.4204 0.5159 0.3316 0.031 Uiso 1 1 calc R . . . .
C6 C 0.1583(5) 0.53314(9) 0.2292(4) 0.0195(7) Uani 1 1 d . . . . .
C7 C 0.1961(5) 0.68730(9) -0.1640(4) 0.0192(7) Uani 1 1 d . . . . .
C8 C 0.1347(5) 0.70702(9) -0.3217(5) 0.0249(8) Uani 1 1 d . . . . .
H7 H 0.1137 0.7311 -0.3187 0.030 Uiso 1 1 calc R . . . .
C9 C 0.1078(5) 0.68857(10) -0.4800(5) 0.0284(9) Uani 1 1 d . . . . .
H8 H 0.0695 0.7005 -0.5885 0.034 Uiso 1 1 calc R . . . .
C10 C 0.1361(5) 0.65205(10) -0.4845(5) 0.0302(9) Uani 1 1 d . . . . .
H9 H 0.1135 0.6406 -0.5957 0.036 Uiso 1 1 calc R . . . .
C11 C 0.1962(5) 0.63269(9) -0.3300(5) 0.0249(8) Uani 1 1 d . . . . .
H10 H 0.2158 0.6086 -0.3338 0.030 Uiso 1 1 calc R . . . .
C12 C 0.2263(5) 0.65137(8) -0.1656(4) 0.0188(7) Uani 1 1 d . . . . .
Cl1 Cl 0.48191(11) 0.56343(2) -0.09874(11) 0.02327(19) Uani 1 1 d . . . . .
Cl2 Cl 0.60017(13) 0.60218(2) 0.36316(11) 0.0268(2) Uani 1 1 d . . . . .
N1 N 0.1663(4) 0.56661(7) 0.1646(4) 0.0209(6) Uani 1 1 d . . . . .
N2 N -0.0013(4) 0.57756(8) 0.0943(4) 0.0283(7) Uani 1 1 d . . . . .
N3 N -0.1154(4) 0.55201(9) 0.1153(4) 0.0306(7) Uani 1 1 d . . . . .
H1 H -0.2327 0.5533 0.0806 0.037 Uiso 1 1 calc R . . . .
N4 N 0.2873(4) 0.64090(7) 0.0099(4) 0.0199(6) Uani 1 1 d . . . . .
N5 N 0.2963(4) 0.66842(7) 0.1174(4) 0.0214(6) Uani 1 1 d . . . . .
N6 N 0.2415(4) 0.69617(7) 0.0143(4) 0.0223(7) Uani 1 1 d . . . . .
H6 H 0.2353 0.7171 0.0549 0.027 Uiso 1 1 calc R . . . .
Zn1 Zn 0.38300(6) 0.59423(2) 0.11647(5) 0.01956(11) Uani 1 1 d . . . . .
C13 C -0.3365(5) 0.67797(9) -0.3218(4) 0.0194(7) Uani 1 1 d . . . . .
C14 C -0.3178(5) 0.64830(9) -0.2092(5) 0.0274(8) Uani 1 1 d . . . . .
H12 H -0.3419 0.6257 -0.2552 0.033 Uiso 1 1 calc R . . . .
C15 C -0.2624(5) 0.65451(10) -0.0284(5) 0.0277(8) Uani 1 1 d . . . . .
H13 H -0.2489 0.6356 0.0512 0.033 Uiso 1 1 calc R . . . .
C16 C -0.2251(5) 0.68860(11) 0.0418(5) 0.0304(9) Uani 1 1 d . . . . .
H14 H -0.1900 0.6916 0.1663 0.036 Uiso 1 1 calc R . . . .
C17 C -0.2391(5) 0.71752(10) -0.0685(5) 0.0258(8) Uani 1 1 d . . . . .
H15 H -0.2118 0.7400 -0.0224 0.031 Uiso 1 1 calc R . . . .
C18 C -0.2968(5) 0.71140(9) -0.2542(5) 0.0204(7) Uani 1 1 d . . . . .
N7 N -0.3234(4) 0.73460(7) -0.3977(4) 0.0268(7) Uani 1 1 d . . . . .
N8 N -0.3803(5) 0.71684(8) -0.5471(4) 0.0304(8) Uani 1 1 d . . . . .
N9 N -0.3878(4) 0.68282(7) -0.5029(4) 0.0265(7) Uani 1 1 d . . . . .
H11 H -0.4210 0.6662 -0.5798 0.032 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.405(5) . ?
C1 C6 1.396(5) . ?
C1 N3 1.352(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.366(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.412(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.405(5) . ?
C6 N1 1.370(4) . ?
C7 C8 1.404(4) . ?
C7 C12 1.387(4) . ?
C7 N6 1.362(4) . ?
C8 H7 0.9300 . ?
C8 C9 1.366(5) . ?
C9 H8 0.9300 . ?
C9 C10 1.408(5) . ?
C10 H9 0.9300 . ?
C10 C11 1.375(5) . ?
C11 H10 0.9300 . ?
C11 C12 1.408(4) . ?
C12 N4 1.370(4) . ?
Cl1 Zn1 2.2478(9) . ?
Cl2 Zn1 2.2223(10) . ?
N1 N2 1.319(4) . ?
N1 Zn1 2.020(3) . ?
N2 N3 1.322(4) . ?
N3 H1 0.8600 . ?
N4 N5 1.319(4) . ?
N4 Zn1 2.019(3) . ?
N5 N6 1.327(4) . ?
N6 H6 0.8600 . ?
C13 C14 1.404(5) . ?
C13 C18 1.381(4) . ?
C13 N9 1.356(4) . ?
C14 H12 0.9300 . ?
C14 C15 1.364(5) . ?
C15 H13 0.9300 . ?
C15 C16 1.408(5) . ?
C16 H14 0.9300 . ?
C16 C17 1.372(5) . ?
C17 H15 0.9300 . ?
C17 C18 1.399(5) . ?
C18 N7 1.381(4) . ?
N7 N8 1.309(4) . ?
N8 N9 1.342(4) . ?
N9 H11 0.8600 . ?

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
C6 C1 C2 122.1(4) . . ?
N3 C1 C2 134.0(4) . . ?
N3 C1 C6 103.9(3) . . ?
C1 C2 H2 122.1 . . ?
C3 C2 C1 115.9(4) . . ?
C3 C2 H2 122.1 . . ?
C2 C3 H3 118.6 . . ?
C2 C3 C4 122.7(4) . . ?
C4 C3 H3 118.6 . . ?
C3 C4 H4 119.2 . . ?
C5 C4 C3 121.6(4) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 H5 121.7 . . ?
C4 C5 C6 116.6(4) . . ?
C6 C5 H5 121.7 . . ?
C1 C6 C5 121.2(3) . . ?
N1 C6 C1 107.2(3) . . ?
N1 C6 C5 131.6(3) . . ?
C12 C7 C8 123.0(3) . . ?
N6 C7 C8 132.7(3) . . ?
N6 C7 C12 104.2(3) . . ?
C7 C8 H7 122.2 . . ?
C9 C8 C7 115.6(3) . . ?
C9 C8 H7 122.2 . . ?
C8 C9 H8 118.9 . . ?
C8 C9 C10 122.2(3) . . ?
C10 C9 H8 118.9 . . ?
C9 C10 H9 118.9 . . ?
C11 C10 C9 122.2(3) . . ?
C11 C10 H9 118.9 . . ?
C10 C11 H10 121.9 . . ?
C10 C11 C12 116.3(3) . . ?
C12 C11 H10 121.9 . . ?
C7 C12 C11 120.6(3) . . ?
N4 C12 C7 107.5(3) . . ?
N4 C12 C11 131.9(3) . . ?
C6 N1 Zn1 130.0(2) . . ?
N2 N1 C6 109.3(3) . . ?
N2 N1 Zn1 119.1(2) . . ?
N1 N2 N3 107.2(3) . . ?
C1 N3 H1 123.8 . . ?
N2 N3 C1 112.3(3) . . ?
N2 N3 H1 123.8 . . ?
C12 N4 Zn1 131.4(2) . . ?
N5 N4 C12 109.2(3) . . ?
N5 N4 Zn1 119.0(2) . . ?
N4 N5 N6 107.5(3) . . ?
C7 N6 H6 124.2 . . ?
N5 N6 C7 111.5(3) . . ?
N5 N6 H6 124.2 . . ?
Cl2 Zn1 Cl1 112.83(4) . . ?
N1 Zn1 Cl1 104.53(8) . . ?
N1 Zn1 Cl2 112.94(9) . . ?
N4 Zn1 Cl1 108.17(8) . . ?
N4 Zn1 Cl2 110.51(8) . . ?
N4 Zn1 N1 107.51(11) . . ?
C18 C13 C14 122.1(3) . . ?
N9 C13 C14 133.9(3) . . ?
N9 C13 C18 104.0(3) . . ?
C13 C14 H12 122.0 . . ?
C15 C14 C13 116.0(3) . . ?
C15 C14 H12 122.0 . . ?
C14 C15 H13 118.9 . . ?
C14 C15 C16 122.2(3) . . ?
C16 C15 H13 118.9 . . ?
C15 C16 H14 119.1 . . ?
C17 C16 C15 121.8(3) . . ?
C17 C16 H14 119.1 . . ?
C16 C17 H15 121.8 . . ?
C16 C17 C18 116.4(3) . . ?
C18 C17 H15 121.8 . . ?
C13 C18 C17 121.5(3) . . ?
C13 C18 N7 108.3(3) . . ?
N7 C18 C17 130.2(3) . . ?
N8 N7 C18 108.4(3) . . ?
N7 N8 N9 107.9(3) . . ?
C13 N9 H11 124.3 . . ?
N8 N9 C13 111.4(3) . . ?
N8 N9 H11 124.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 0.2(5) . . . . ?
C1 C6 N1 N2 -0.8(4) . . . . ?
C1 C6 N1 Zn1 -166.2(2) . . . . ?
C2 C1 C6 C5 0.3(5) . . . . ?
C2 C1 C6 N1 179.1(3) . . . . ?
C2 C1 N3 N2 -178.3(4) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
C3 C4 C5 C6 0.0(5) . . . . ?
C4 C5 C6 C1 -0.1(5) . . . . ?
C4 C5 C6 N1 -178.6(3) . . . . ?
C5 C6 N1 N2 177.8(4) . . . . ?
C5 C6 N1 Zn1 12.4(5) . . . . ?
C6 C1 C2 C3 -0.3(5) . . . . ?
C6 C1 N3 N2 0.2(4) . . . . ?
C6 N1 N2 N3 0.9(4) . . . . ?
C7 C8 C9 C10 1.3(5) . . . . ?
C7 C12 N4 N5 -0.2(4) . . . . ?
C7 C12 N4 Zn1 -173.3(2) . . . . ?
C8 C7 C12 C11 0.1(5) . . . . ?
C8 C7 C12 N4 179.2(3) . . . . ?
C8 C7 N6 N5 -178.9(4) . . . . ?
C8 C9 C10 C11 -1.3(6) . . . . ?
C9 C10 C11 C12 0.6(6) . . . . ?
C10 C11 C12 C7 -0.1(5) . . . . ?
C10 C11 C12 N4 -178.9(4) . . . . ?
C11 C12 N4 N5 178.7(4) . . . . ?
C11 C12 N4 Zn1 5.6(6) . . . . ?
C12 C7 C8 C9 -0.7(5) . . . . ?
C12 C7 N6 N5 0.2(4) . . . . ?
C12 N4 N5 N6 0.3(4) . . . . ?
N1 N2 N3 C1 -0.7(4) . . . . ?
N3 C1 C2 C3 177.9(4) . . . . ?
N3 C1 C6 C5 -178.4(3) . . . . ?
N3 C1 C6 N1 0.4(4) . . . . ?
N4 N5 N6 C7 -0.3(4) . . . . ?
N6 C7 C8 C9 178.2(4) . . . . ?
N6 C7 C12 C11 -179.0(3) . . . . ?
N6 C7 C12 N4 0.0(4) . . . . ?
Zn1 N1 N2 N3 168.2(2) . . . . ?
Zn1 N4 N5 N6 174.4(2) . . . . ?
C13 C14 C15 C16 -0.3(5) . . . . ?
C13 C18 N7 N8 1.2(4) . . . . ?
C14 C13 C18 C17 -1.3(5) . . . . ?
C14 C13 C18 N7 178.3(3) . . . . ?
C14 C13 N9 N8 -178.8(4) . . . . ?
C14 C15 C16 C17 -1.3(6) . . . . ?
C15 C16 C17 C18 1.5(5) . . . . ?
C16 C17 C18 C13 -0.3(5) . . . . ?
C16 C17 C18 N7 -179.8(4) . . . . ?
C17 C18 N7 N8 -179.2(3) . . . . ?
C18 C13 C14 C15 1.5(5) . . . . ?
C18 C13 N9 N8 0.3(4) . . . . ?
C18 N7 N8 N9 -1.0(4) . . . . ?
N7 N8 N9 C13 0.4(4) . . . . ?
N9 C13 C14 C15 -179.5(4) . . . . ?
N9 C13 C18 C17 179.5(3) . . . . ?
N9 C13 C18 N7 -0.9(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
