# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

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

data_2b
_database_code_depnum_ccdc_archive 'CCDC 1582538'
_audit_update_record             
;
2017-10-27 deposited with the CCDC.
2017-12-04 downloaded from the CCDC.
;
_audit_creation_date             2017-10-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H22 Br2 N2 Ni O4'
_chemical_formula_sum            'C20 H22 Br2 N2 Ni O4'
_chemical_formula_weight         572.92
_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'
Br Br -0.2901 2.4595 '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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.9966(5)
_cell_length_b                   9.5422(7)
_cell_length_c                   15.2152(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.623(6)
_cell_angle_gamma                90
_cell_volume                     1150.74(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1157
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.9290
_cell_measurement_theta_min      4.9660
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.342
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark blue'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4420
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_min         4.481
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1505
_reflns_number_total             2243
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.824
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         2243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0463
_refine_ls_restrained_S_all      1.027
_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)+(0.0631P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1204
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C4(H4), C3(H3), C8(H8)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Ni1 Ni 0.5000 0.5000 0.5000 0.0376(2) Uani 1 2 d S T P . .
Br1 Br 0.15055(9) 0.05581(6) 0.29514(4) 0.0806(3) Uani 1 1 d . . . . .
O1 O 0.2923(3) 0.5677(3) 0.42318(18) 0.0455(8) Uani 1 1 d . . . . .
O2 O 0.3995(4) 0.5453(3) 0.61152(18) 0.0451(7) Uani 1 1 d . . . . .
N1 N 0.3963(4) 0.2952(4) 0.4953(2) 0.0405(8) Uani 1 1 d . . . . .
C7 C 0.1709(5) 0.6286(4) 0.4508(3) 0.0403(10) Uani 1 1 d . . . . .
C1 C 0.3190(5) 0.2463(5) 0.4175(3) 0.0458(11) Uani 1 1 d . . . . .
H1 H 0.3110 0.3040 0.3679 0.055 Uiso 1 1 calc R . . . .
C9 C 0.2659(5) 0.6140(5) 0.6124(3) 0.0418(10) Uani 1 1 d . . . . .
C2 C 0.2520(6) 0.1148(5) 0.4089(3) 0.0484(11) Uani 1 1 d . . . . .
C5 C 0.4040(6) 0.2106(5) 0.5653(3) 0.0513(12) Uani 1 1 d . . . . .
H5 H 0.4580 0.2422 0.6196 0.062 Uiso 1 1 calc R . . . .
C4 C 0.3354(7) 0.0784(5) 0.5606(3) 0.0605(14) Uani 1 1 d . . . . .
H4 H 0.3402 0.0234 0.6114 0.073 Uiso 1 1 calc R . . . .
C3 C 0.2600(7) 0.0279(5) 0.4811(4) 0.0593(14) Uani 1 1 d . . . . .
H3 H 0.2156 -0.0623 0.4761 0.071 Uiso 1 1 calc R . . . .
C8 C 0.1560(6) 0.6557(5) 0.5395(3) 0.0497(12) Uani 1 1 d . . . . .
H8 H 0.0623 0.7071 0.5507 0.060 Uiso 1 1 calc R . . . .
C6 C 0.0322(6) 0.6749(6) 0.3800(3) 0.0621(14) Uani 1 1 d . . . . .
H6A H 0.0796 0.7284 0.3360 0.093 Uiso 1 1 calc GR . . . .
H6B H -0.0471 0.7316 0.4062 0.093 Uiso 1 1 calc GR . . . .
H6C H -0.0243 0.5940 0.3528 0.093 Uiso 1 1 calc GR . . . .
C10 C 0.2234(7) 0.6513(7) 0.7041(3) 0.0749(17) Uani 1 1 d . . . . .
H10A H 0.2230 0.5678 0.7392 0.112 Uiso 1 1 calc GR . . . .
H10B H 0.1140 0.6944 0.6987 0.112 Uiso 1 1 calc GR . . . .
H10C H 0.3062 0.7154 0.7323 0.112 Uiso 1 1 calc GR . . . .


_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
Ni1 O1 2.007(3) 3_666 ?
Ni1 O1 2.007(3) . ?
Ni1 O2 2.018(3) 3_666 ?
Ni1 O2 2.018(3) . ?
Ni1 N1 2.120(4) 3_666 ?
Ni1 N1 2.120(4) . ?
Br1 O1 3.415(3) 2_545 ?
Br1 O2 3.358(3) 4_565 ?
Br1 C2 1.896(4) . ?
O1 C7 1.251(5) . ?
O2 C9 1.255(5) . ?
N1 C1 1.344(5) . ?
N1 C5 1.331(6) . ?
C7 C8 1.396(6) . ?
C7 C6 1.505(6) . ?
C1 H1 0.9300 . ?
C1 C2 1.364(6) . ?
C9 C8 1.379(6) . ?
C9 C10 1.521(6) . ?
C2 C3 1.371(7) . ?
C5 H5 0.9300 . ?
C5 C4 1.374(7) . ?
C4 H4 0.9300 . ?
C4 C3 1.365(7) . ?
C3 H3 0.9300 . ?
C8 H8 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 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
O1 Ni1 O1 180.00(16) 3_666 . ?
O1 Ni1 O2 88.30(12) . 3_666 ?
O1 Ni1 O2 91.69(12) . . ?
O1 Ni1 O2 91.70(12) 3_666 3_666 ?
O1 Ni1 O2 88.30(12) 3_666 . ?
O1 Ni1 N1 90.70(13) . 3_666 ?
O1 Ni1 N1 89.30(13) . . ?
O1 Ni1 N1 90.70(13) 3_666 . ?
O1 Ni1 N1 89.30(13) 3_666 3_666 ?
O2 Ni1 O2 180.00(14) 3_666 . ?
O2 Ni1 N1 91.61(12) . . ?
O2 Ni1 N1 88.39(12) 3_666 . ?
O2 Ni1 N1 88.38(12) . 3_666 ?
O2 Ni1 N1 91.62(12) 3_666 3_666 ?
N1 Ni1 N1 180.0 3_666 . ?
O2 Br1 O1 48.90(7) 4_565 2_545 ?
C2 Br1 O1 141.40(15) . 2_545 ?
C2 Br1 O2 168.66(15) . 4_565 ?
C7 O1 Ni1 125.0(3) . . ?
C9 O2 Ni1 123.7(3) . . ?
C1 N1 Ni1 118.8(3) . . ?
C5 N1 Ni1 123.8(3) . . ?
C5 N1 C1 117.4(4) . . ?
O1 C7 C8 125.5(4) . . ?
O1 C7 C6 115.3(4) . . ?
C8 C7 C6 119.2(4) . . ?
N1 C1 H1 118.9 . . ?
N1 C1 C2 122.2(4) . . ?
C2 C1 H1 118.9 . . ?
O2 C9 C8 126.5(4) . . ?
O2 C9 C10 115.3(4) . . ?
C8 C9 C10 118.3(4) . . ?
C1 C2 Br1 118.4(3) . . ?
C1 C2 C3 120.2(4) . . ?
C3 C2 Br1 121.4(4) . . ?
N1 C5 H5 118.7 . . ?
N1 C5 C4 122.7(4) . . ?
C4 C5 H5 118.7 . . ?
C5 C4 H4 120.1 . . ?
C3 C4 C5 119.8(5) . . ?
C3 C4 H4 120.1 . . ?
C2 C3 H3 121.1 . . ?
C4 C3 C2 117.7(5) . . ?
C4 C3 H3 121.1 . . ?
C7 C8 H8 116.6 . . ?
C9 C8 C7 126.7(4) . . ?
C9 C8 H8 116.6 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_olex2_date_sample_data_collection 2017-03-05
_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_7a
_database_code_depnum_ccdc_archive 'CCDC 1582544'
_audit_update_record             
;
2017-10-27 deposited with the CCDC.
2017-12-04 downloaded from the CCDC.
;
_audit_creation_date             2017-10-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H20 Br2 Co N4 O4'
_chemical_formula_sum            'C18 H20 Br2 Co N4 O4'
_chemical_formula_weight         575.13
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H18 N4 O4 Co Br2'
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'
Br Br -0.2901 2.4595 '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'
O O 0.0106 0.0060 '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                   6.1501(4)
_cell_length_b                   8.7162(7)
_cell_length_c                   10.7960(8)
_cell_angle_alpha                100.733(6)
_cell_angle_beta                 97.813(6)
_cell_angle_gamma                101.437(7)
_cell_volume                     548.26(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1534
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      28.6360
_cell_measurement_theta_min      4.5820
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.457
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light orange'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.742
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             285
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4740
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_min         4.247
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   23.00   49.00   1.0000    6.1550
omega____ theta____ kappa____ phi______ frames
    -       22.4994   57.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega   -1.00   63.00   1.0000    6.1550
omega____ theta____ kappa____ phi______ frames
    -       22.4994   77.0000  -30.0000 64

#__ type_ start__ end____ width___ exp.time_
  3 omega   15.00   85.00   1.0000    6.1550
omega____ theta____ kappa____ phi______ frames
    -       22.4994   57.0000  -90.0000 70

#__ type_ start__ end____ width___ exp.time_
  4 omega   -3.00   49.00   1.0000    6.1550
omega____ theta____ kappa____ phi______ frames
    -       22.4994   77.0000 -150.0000 52

#__ type_ start__ end____ width___ exp.time_
  5 omega   -3.00   90.00   1.0000    6.1550
omega____ theta____ kappa____ phi______ frames
    -       22.4994   19.0000 -180.0000 93

#__ type_ start__ end____ width___ exp.time_
  6 omega  -25.00    6.00   1.0000    6.1550
omega____ theta____ kappa____ phi______ frames
    -       22.4994  -99.0000 -180.0000 31

#__ type_ start__ end____ width___ exp.time_
  7 omega  -46.00   34.00   1.0000    6.1550
omega____ theta____ kappa____ phi______ frames
    -       22.4994  -37.0000    0.0000 80

#__ type_ start__ end____ width___ exp.time_
  8 omega   29.00   65.00   1.0000    6.1550
omega____ theta____ kappa____ phi______ frames
    -       22.4994 -110.0000  108.0000 36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0252396000
_diffrn_orient_matrix_UB_12      0.0540978000
_diffrn_orient_matrix_UB_13      0.0606162000
_diffrn_orient_matrix_UB_21      -0.0522535000
_diffrn_orient_matrix_UB_22      0.0545767000
_diffrn_orient_matrix_UB_23      -0.0272434000
_diffrn_orient_matrix_UB_31      -0.1045919000
_diffrn_orient_matrix_UB_32      -0.0365682000
_diffrn_orient_matrix_UB_33      0.0142833000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1782
_reflns_number_total             2153
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    ?
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         2153
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0330
_refine_ls_restrained_S_all      1.052
_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)+(0.0425P)²+0.0083P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0818
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C7(H7), C4(H4), C3(H3)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Br1 Br 0.44699(6) 0.76004(5) 0.03042(3) 0.06784(16) Uani 1 1 d . . . . .
Co1 Co 0.5000 0.5000 0.5000 0.03681(15) Uani 1 2 d S T P . .
O1 O 0.6612(3) 0.3197(2) 0.49869(18) 0.0453(5) Uani 1 1 d . . . . .
O2 O 0.2456(3) 0.3514(3) 0.36433(18) 0.0474(5) Uani 1 1 d . . . . .
N1 N 0.6500(3) 0.5709(3) 0.3359(2) 0.0415(5) Uani 1 1 d . . . . .
C1 C 0.5285(4) 0.6293(3) 0.2514(3) 0.0419(6) Uani 1 1 d . . . . .
H1 H 0.3831 0.6377 0.2612 0.050 Uiso 1 1 calc R . . . .
C6 C 0.6150(5) 0.1897(4) 0.4154(3) 0.0450(7) Uani 1 1 d . . . . .
C2 C 0.6148(5) 0.6769(4) 0.1505(3) 0.0448(6) Uani 1 1 d . . . . .
C8 C 0.2629(5) 0.2235(4) 0.2928(3) 0.0476(7) Uani 1 1 d . . . . .
N2 N 0.9513(4) 0.6015(4) 0.2200(3) 0.0782(10) Uani 1 1 d . . . . .
C7 C 0.4343(6) 0.1445(4) 0.3127(3) 0.0562(8) Uani 1 1 d . . . . .
H7 H 0.4288 0.0525 0.2516 0.067 Uiso 1 1 calc R . . . .
C4 C 0.8556(5) 0.5595(4) 0.3162(3) 0.0571(8) Uani 1 1 d . . . . .
H4 H 0.9402 0.5186 0.3747 0.068 Uiso 1 1 calc R . . . .
C3 C 0.8297(5) 0.6616(5) 0.1388(3) 0.0705(10) Uani 1 1 d . . . . .
H3 H 0.8916 0.6946 0.0715 0.085 Uiso 1 1 calc R . . . .
C5 C 0.7700(6) 0.0781(4) 0.4351(4) 0.0680(10) Uani 1 1 d . . . . .
H5A H 0.9240 0.1362 0.4475 0.102 Uiso 1 1 calc GR . . . .
H5B H 0.7392 -0.0085 0.3611 0.102 Uiso 1 1 calc GR . . . .
H5C H 0.7451 0.0357 0.5093 0.102 Uiso 1 1 calc GR . . . .
C9 C 0.0738(6) 0.1532(5) 0.1787(3) 0.0782(12) Uani 1 1 d . . . . .
H9A H -0.0617 0.1106 0.2076 0.117 Uiso 1 1 calc GR . . . .
H9B H 0.1140 0.0690 0.1219 0.117 Uiso 1 1 calc GR . . . .
H9C H 0.0493 0.2356 0.1341 0.117 Uiso 1 1 calc GR . . . .


_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
Br1 C2 1.885(3) . ?
Co1 O1 2.0163(18) . ?
Co1 O1 2.0163(18) 2_666 ?
Co1 O2 2.0343(19) . ?
Co1 O2 2.034(2) 2_666 ?
Co1 N1 2.236(2) . ?
Co1 N1 2.236(2) 2_666 ?
O1 C6 1.264(3) . ?
O2 C8 1.265(4) . ?
N1 C1 1.337(3) . ?
N1 C4 1.330(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.370(4) . ?
C6 C7 1.396(4) . ?
C6 C5 1.513(4) . ?
C2 C3 1.374(4) . ?
C8 C7 1.383(4) . ?
C8 C9 1.514(4) . ?
N2 C4 1.335(4) . ?
N2 C3 1.323(4) . ?
C7 H7 0.9300 . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 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
O1 Co1 O1 180.00(11) . 2_666 ?
O1 Co1 O2 90.49(8) 2_666 . ?
O1 Co1 O2 89.51(8) 2_666 2_666 ?
O1 Co1 O2 89.51(8) . . ?
O1 Co1 O2 90.49(8) . 2_666 ?
O1 Co1 N1 88.18(8) 2_666 . ?
O1 Co1 N1 91.82(8) 2_666 2_666 ?
O1 Co1 N1 88.18(8) . 2_666 ?
O1 Co1 N1 91.82(8) . . ?
O2 Co1 O2 180.0 . 2_666 ?
O2 Co1 N1 94.13(8) 2_666 . ?
O2 Co1 N1 85.87(8) . . ?
O2 Co1 N1 94.13(8) . 2_666 ?
O2 Co1 N1 85.87(8) 2_666 2_666 ?
N1 Co1 N1 180.0 . 2_666 ?
C6 O1 Co1 126.09(18) . . ?
C8 O2 Co1 124.50(18) . . ?
C1 N1 Co1 118.97(17) . . ?
C4 N1 Co1 124.10(19) . . ?
C4 N1 C1 116.9(2) . . ?
N1 C1 H1 119.5 . . ?
N1 C1 C2 121.0(2) . . ?
C2 C1 H1 119.5 . . ?
O1 C6 C7 124.9(3) . . ?
O1 C6 C5 114.9(3) . . ?
C7 C6 C5 120.2(3) . . ?
C1 C2 Br1 121.8(2) . . ?
C1 C2 C3 117.8(3) . . ?
C3 C2 Br1 120.4(2) . . ?
O2 C8 C7 125.5(3) . . ?
O2 C8 C9 115.3(3) . . ?
C7 C8 C9 119.2(3) . . ?
C3 N2 C4 116.3(3) . . ?
C6 C7 H7 116.9 . . ?
C8 C7 C6 126.3(3) . . ?
C8 C7 H7 116.9 . . ?
N1 C4 N2 125.8(3) . . ?
N1 C4 H4 117.1 . . ?
N2 C4 H4 117.1 . . ?
C2 C3 H3 118.9 . . ?
N2 C3 C2 122.2(3) . . ?
N2 C3 H3 118.9 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C6 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 N2 0.93 2.58 3.475(4) 162.2 1_455
C4 H4 O1 0.93 2.62 3.209(4) 121.8 2_766
C4 H4 O2 0.93 2.60 3.324(4) 135.4 1_655

_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_4b
_database_code_depnum_ccdc_archive 'CCDC 1582545'
_audit_update_record             
;
2017-10-27 deposited with the CCDC.
2017-12-04 downloaded from the CCDC.
;
_audit_creation_date             2017-10-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H20 Cl2 N4 Ni O4'
_chemical_formula_sum            'C18 H20 Cl2 N4 Ni O4'
_chemical_formula_weight         485.99
_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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.3212(5)
_cell_length_b                   8.9502(7)
_cell_length_c                   10.0197(8)
_cell_angle_alpha                100.977(7)
_cell_angle_beta                 100.919(7)
_cell_angle_gamma                99.073(6)
_cell_volume                     535.27(8)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1303
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.3260
_cell_measurement_theta_min      4.4570
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.187
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96620
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light blue'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             250
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4103
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         4.151
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1803
_reflns_number_total             2100
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    ?
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         2100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.061
_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)+(0.0413P)²+0.0017P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0859
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C3(H3), C7(H7)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Ni1 Ni 0.5000 0.5000 0.5000 0.04007(16) Uani 1 2 d S T P . .
Cl1 Cl 0.50170(15) 0.22183(11) 0.96731(9) 0.0824(3) Uani 1 1 d . . . . .
O1 O 0.6739(3) 0.3329(2) 0.51164(18) 0.0493(4) Uani 1 1 d . . . . .
O2 O 0.2572(3) 0.3560(2) 0.35073(18) 0.0502(4) Uani 1 1 d . . . . .
N1 N 0.3513(3) 0.4370(2) 0.6651(2) 0.0441(5) Uani 1 1 d . . . . .
N2 N 0.1921(4) 0.3706(3) 0.8935(3) 0.0664(7) Uani 1 1 d . . . . .
C1 C 0.4498(4) 0.3578(3) 0.7496(3) 0.0489(6) Uani 1 1 d . . . . .
H1 H 0.5758 0.3234 0.7330 0.059 Uiso 1 1 calc R . . . .
C6 C 0.6271(4) 0.2006(3) 0.4286(3) 0.0495(6) Uani 1 1 d . . . . .
C8 C 0.2687(4) 0.2216(3) 0.2880(3) 0.0517(6) Uani 1 1 d . . . . .
C4 C 0.1713(4) 0.4824(3) 0.6949(3) 0.0532(7) Uani 1 1 d . . . . .
H4 H 0.0960 0.5369 0.6382 0.064 Uiso 1 1 calc R . . . .
C2 C 0.3679(4) 0.3262(3) 0.8610(3) 0.0521(6) Uani 1 1 d . . . . .
C3 C 0.0950(5) 0.4497(4) 0.8082(3) 0.0668(8) Uani 1 1 d . . . . .
H3 H -0.0301 0.4845 0.8261 0.080 Uiso 1 1 calc R . . . .
C7 C 0.4421(5) 0.1466(3) 0.3198(3) 0.0594(7) Uani 1 1 d . . . . .
H7 H 0.4332 0.0501 0.2622 0.071 Uiso 1 1 calc R . . . .
C5 C 0.7929(5) 0.0992(3) 0.4563(4) 0.0756(10) Uani 1 1 d . . . . .
H5A H 0.9376 0.1559 0.4615 0.113 Uiso 1 1 calc GR . . . .
H5B H 0.7582 0.0079 0.3819 0.113 Uiso 1 1 calc GR . . . .
H5C H 0.7882 0.0695 0.5430 0.113 Uiso 1 1 calc GR . . . .
C9 C 0.0749(5) 0.1404(4) 0.1694(3) 0.0814(10) Uani 1 1 d . . . . .
H9A H -0.0585 0.1613 0.1946 0.122 Uiso 1 1 calc GR . . . .
H9B H 0.0696 0.0304 0.1511 0.122 Uiso 1 1 calc GR . . . .
H9C H 0.0902 0.1776 0.0874 0.122 Uiso 1 1 calc GR . . . .


_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
Ni1 O1 1.9984(15) 2_666 ?
Ni1 O1 1.9984(15) . ?
Ni1 O2 2.0067(17) 2_666 ?
Ni1 O2 2.0067(17) . ?
Ni1 N1 2.1714(19) 2_666 ?
Ni1 N1 2.1714(19) . ?
Cl1 C2 1.735(3) . ?
O1 C6 1.266(3) . ?
O2 C8 1.266(3) . ?
N1 C1 1.333(3) . ?
N1 C4 1.333(3) . ?
N2 C2 1.314(3) . ?
N2 C3 1.333(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.373(3) . ?
C6 C7 1.388(4) . ?
C6 C5 1.512(3) . ?
C8 C7 1.391(4) . ?
C8 C9 1.510(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.377(4) . ?
C3 H3 0.9300 . ?
C7 H7 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 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
O1 Ni1 O1 180.0 2_666 . ?
O1 Ni1 O2 91.77(7) . . ?
O1 Ni1 O2 88.23(7) . 2_666 ?
O1 Ni1 O2 88.23(7) 2_666 . ?
O1 Ni1 O2 91.77(7) 2_666 2_666 ?
O1 Ni1 N1 90.50(7) . 2_666 ?
O1 Ni1 N1 89.50(7) . . ?
O1 Ni1 N1 90.51(7) 2_666 . ?
O1 Ni1 N1 89.50(7) 2_666 2_666 ?
O2 Ni1 O2 180.0 . 2_666 ?
O2 Ni1 N1 92.26(7) 2_666 2_666 ?
O2 Ni1 N1 87.74(7) . 2_666 ?
O2 Ni1 N1 87.74(7) 2_666 . ?
O2 Ni1 N1 92.26(7) . . ?
N1 Ni1 N1 180.0 2_666 . ?
C6 O1 Ni1 125.06(17) . . ?
C8 O2 Ni1 124.62(17) . . ?
C1 N1 Ni1 119.74(15) . . ?
C4 N1 Ni1 123.74(16) . . ?
C4 N1 C1 116.4(2) . . ?
C2 N2 C3 114.5(2) . . ?
N1 C1 H1 119.5 . . ?
N1 C1 C2 120.9(2) . . ?
C2 C1 H1 119.5 . . ?
O1 C6 C7 125.3(2) . . ?
O1 C6 C5 114.3(3) . . ?
C7 C6 C5 120.4(3) . . ?
O2 C8 C7 125.4(2) . . ?
O2 C8 C9 115.4(3) . . ?
C7 C8 C9 119.2(3) . . ?
N1 C4 H4 119.5 . . ?
N1 C4 C3 121.1(2) . . ?
C3 C4 H4 119.5 . . ?
N2 C2 Cl1 116.9(2) . . ?
N2 C2 C1 124.0(2) . . ?
C1 C2 Cl1 119.1(2) . . ?
N2 C3 C4 123.1(2) . . ?
N2 C3 H3 118.5 . . ?
C4 C3 H3 118.5 . . ?
C6 C7 C8 126.8(3) . . ?
C6 C7 H7 116.6 . . ?
C8 C7 H7 116.6 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C6 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4 O2 0.93 2.58 3.265(3) 131.1 2_566
C3 H3 O2 0.93 2.81 3.384(3) 121.1 2_566

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
Ni1 O1 C6 C7 -3.2(4) . . . . ?
Ni1 O1 C6 C5 176.84(15) . . . . ?
Ni1 O2 C8 C7 5.9(3) . . . . ?
Ni1 O2 C8 C9 -174.07(17) . . . . ?
Ni1 N1 C1 C2 175.3(2) . . . . ?
Ni1 N1 C4 C3 -174.5(2) . . . . ?
O1 C6 C7 C8 -4.8(4) . . . . ?
O2 C8 C7 C6 3.3(4) . . . . ?
N1 C1 C2 Cl1 179.69(19) . . . . ?
N1 C1 C2 N2 -0.4(4) . . . . ?
N1 C4 C3 N2 -0.8(5) . . . . ?
C1 N1 C4 C3 0.7(4) . . . . ?
C4 N1 C1 C2 -0.2(4) . . . . ?
C2 N2 C3 C4 0.2(5) . . . . ?
C3 N2 C2 Cl1 -179.7(2) . . . . ?
C3 N2 C2 C1 0.4(4) . . . . ?
C5 C6 C7 C8 175.1(3) . . . . ?
C9 C8 C7 C6 -176.8(3) . . . . ?

_olex2_date_sample_data_collection 2016-03-30
_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_5a
_database_code_depnum_ccdc_archive 'CCDC 1582546'
_audit_update_record             
;
2017-10-27 deposited with the CCDC.
2017-12-04 downloaded from the CCDC.
;
_audit_creation_date             2017-10-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H20 Br2 Co N4 O4'
_chemical_formula_sum            'C18 H20 Br2 Co N4 O4'
_chemical_formula_weight         575.13
_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'
Br Br -0.2901 2.4595 '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'
O O 0.0106 0.0060 '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                   6.3290(5)
_cell_length_b                   8.9473(6)
_cell_length_c                   10.2742(7)
_cell_angle_alpha                100.396(6)
_cell_angle_beta                 101.149(7)
_cell_angle_gamma                100.044(6)
_cell_volume                     548.09(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1470
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      30.9810
_cell_measurement_theta_min      4.5090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.459
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark orange'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.742
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             285
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4340
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_min         4.339
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1893
_reflns_number_total             2373
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    ?
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         2373
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0354
_refine_ls_restrained_S_all      1.032
_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)+(0.0407P)²+0.1584P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0864
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C7(H7), C3(H3)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.5000 0.5000 0.5000 0.03464(15) Uani 1 2 d S T P . .
Br1 Br 0.50568(7) 0.21222(4) 0.97161(4) 0.06823(16) Uani 1 1 d . . . . .
O1 O 0.6687(3) 0.3299(2) 0.5134(2) 0.0439(5) Uani 1 1 d . . . . .
O2 O 0.2561(3) 0.3494(2) 0.3528(2) 0.0451(5) Uani 1 1 d . . . . .
N1 N 0.3431(4) 0.4374(3) 0.6666(2) 0.0400(5) Uani 1 1 d . . . . .
N2 N 0.1848(4) 0.3702(3) 0.8890(3) 0.0579(7) Uani 1 1 d . . . . .
C1 C 0.4407(5) 0.3572(3) 0.7488(3) 0.0419(6) Uani 1 1 d . . . . .
H1 H 0.5653 0.3226 0.7323 0.050 Uiso 1 1 calc R . . . .
C6 C 0.6257(5) 0.2000(3) 0.4309(3) 0.0417(7) Uani 1 1 d . . . . .
C4 C 0.1658(5) 0.4831(4) 0.6957(3) 0.0476(7) Uani 1 1 d . . . . .
H4 H 0.0926 0.5389 0.6406 0.057 Uiso 1 1 calc R . . . .
C2 C 0.3589(5) 0.3254(3) 0.8573(3) 0.0439(7) Uani 1 1 d . . . . .
C8 C 0.2690(5) 0.2174(3) 0.2909(3) 0.0445(7) Uani 1 1 d . . . . .
C7 C 0.4430(6) 0.1446(3) 0.3226(3) 0.0509(8) Uani 1 1 d . . . . .
H7 H 0.4363 0.0496 0.2658 0.061 Uiso 1 1 calc R . . . .
C5 C 0.7928(6) 0.1002(4) 0.4575(4) 0.0627(9) Uani 1 1 d . . . . .
H5A H 0.9377 0.1590 0.4633 0.094 Uiso 1 1 calc GR . . . .
H5B H 0.7580 0.0097 0.3845 0.094 Uiso 1 1 calc GR . . . .
H5C H 0.7884 0.0686 0.5416 0.094 Uiso 1 1 calc GR . . . .
C3 C 0.0879(5) 0.4497(4) 0.8056(4) 0.0595(9) Uani 1 1 d . . . . .
H3 H -0.0368 0.4838 0.8225 0.071 Uiso 1 1 calc R . . . .
C9 C 0.0762(6) 0.1350(5) 0.1737(4) 0.0718(11) Uani 1 1 d . . . . .
H9A H -0.0592 0.1446 0.2000 0.108 Uiso 1 1 calc GR . . . .
H9B H 0.0801 0.0269 0.1495 0.108 Uiso 1 1 calc GR . . . .
H9C H 0.0851 0.1812 0.0970 0.108 Uiso 1 1 calc GR . . . .


_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 O1 2.0152(17) . ?
Co1 O1 2.0152(17) 2_666 ?
Co1 O2 2.0304(19) 2_666 ?
Co1 O2 2.0304(19) . ?
Co1 N1 2.245(2) 2_666 ?
Co1 N1 2.245(2) . ?
Br1 C2 1.898(3) . ?
O1 C6 1.261(3) . ?
O2 C8 1.261(3) . ?
N1 C1 1.334(3) . ?
N1 C4 1.327(4) . ?
N2 C2 1.314(4) . ?
N2 C3 1.336(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.371(4) . ?
C6 C7 1.387(4) . ?
C6 C5 1.515(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.376(5) . ?
C8 C7 1.389(4) . ?
C8 C9 1.510(4) . ?
C7 H7 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C3 H3 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 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
O1 Co1 O1 180.0 . 2_666 ?
O1 Co1 O2 90.10(8) 2_666 . ?
O1 Co1 O2 89.90(8) 2_666 2_666 ?
O1 Co1 O2 89.90(8) . . ?
O1 Co1 O2 90.10(8) . 2_666 ?
O1 Co1 N1 89.67(8) 2_666 2_666 ?
O1 Co1 N1 90.33(8) 2_666 . ?
O1 Co1 N1 89.67(8) . . ?
O1 Co1 N1 90.33(8) . 2_666 ?
O2 Co1 O2 180.0 . 2_666 ?
O2 Co1 N1 92.54(8) 2_666 2_666 ?
O2 Co1 N1 87.46(8) . 2_666 ?
O2 Co1 N1 87.46(8) 2_666 . ?
O2 Co1 N1 92.54(8) . . ?
N1 Co1 N1 180.0 2_666 . ?
C6 O1 Co1 125.77(18) . . ?
C8 O2 Co1 125.46(18) . . ?
C1 N1 Co1 118.61(19) . . ?
C4 N1 Co1 124.6(2) . . ?
C4 N1 C1 116.7(3) . . ?
C2 N2 C3 114.8(3) . . ?
N1 C1 H1 119.7 . . ?
N1 C1 C2 120.6(3) . . ?
C2 C1 H1 119.7 . . ?
O1 C6 C7 125.6(2) . . ?
O1 C6 C5 114.7(3) . . ?
C7 C6 C5 119.7(3) . . ?
N1 C4 H4 119.3 . . ?
N1 C4 C3 121.4(3) . . ?
C3 C4 H4 119.3 . . ?
N2 C2 Br1 117.2(2) . . ?
N2 C2 C1 124.0(3) . . ?
C1 C2 Br1 118.8(2) . . ?
O2 C8 C7 125.3(3) . . ?
O2 C8 C9 115.6(3) . . ?
C7 C8 C9 119.0(3) . . ?
C6 C7 C8 126.3(3) . . ?
C6 C7 H7 116.8 . . ?
C8 C7 H7 116.8 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C6 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C3 C4 122.5(3) . . ?
N2 C3 H3 118.7 . . ?
C4 C3 H3 118.7 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4 O2 0.93 2.58 3.282(3) 132.2 2_566
C3 H3 O2 0.93 2.85 3.416(4) 120.4 2_566

_olex2_date_sample_data_collection 2016-02-16
_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_1b
_database_code_depnum_ccdc_archive 'CCDC 1582539'
_audit_update_record             
;
2017-10-27 deposited with the CCDC.
2017-12-04 downloaded from the CCDC.
;
_audit_creation_date             2017-10-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H22 Cl2 N2 Ni O4'
_chemical_formula_sum            'C20 H22 Cl2 N2 Ni O4'
_chemical_formula_weight         484.00
_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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.1894(2)
_cell_length_b                   9.9870(3)
_cell_length_c                   13.4819(5)
_cell_angle_alpha                73.422(3)
_cell_angle_beta                 71.424(3)
_cell_angle_gamma                85.191(2)
_cell_volume                     1124.05(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7138
_cell_measurement_temperature    296(3)
_cell_measurement_theta_max      30.5980
_cell_measurement_theta_min      4.4640
_shelx_estimated_absorpt_T_max   0.823
_shelx_estimated_absorpt_T_min   0.766
_exptl_absorpt_coefficient_mu    1.128
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19684
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         4.258
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4487
_reflns_number_total             5409
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         5409
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0336
_refine_ls_restrained_S_all      1.041
_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)+(0.0405P)²+0.2844P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0882
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C11(H11), C15(H15), C5(H5), C8(H8), C4(H4), C18(H18), C13(H13),
 C3(H3), C14(H14)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C6(H6A,H6B,H6C), C20(H20A,H20B,H20C), C16(H16A,H16B,H16C)
;
_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
Ni2 Ni 0.5000 0.5000 0.5000 0.04465(9) Uani 1 2 d S T P . .
Ni1 Ni 0.0000 0.5000 1.0000 0.04577(9) Uani 1 2 d S T P . .
Cl2 Cl 0.81621(7) 0.94200(7) 0.52993(7) 0.0895(2) Uani 1 1 d . . . . .
Cl1 Cl 0.47508(9) 0.85220(8) 0.96568(8) 0.1071(3) Uani 1 1 d . . . . .
O1 O -0.05772(15) 0.70303(13) 0.97385(11) 0.0549(3) Uani 1 1 d . . . . .
O3 O 0.65959(15) 0.60411(14) 0.36441(11) 0.0580(3) Uani 1 1 d . . . . .
O2 O -0.00010(15) 0.50018(14) 0.85033(10) 0.0573(3) Uani 1 1 d . . . . .
O4 O 0.32923(15) 0.59142(14) 0.44109(12) 0.0593(3) Uani 1 1 d . . . . .
N2 N 0.50485(16) 0.67030(15) 0.56510(12) 0.0473(3) Uani 1 1 d . . . . .
N1 N 0.23480(16) 0.56173(15) 0.94153(12) 0.0485(3) Uani 1 1 d . . . . .
C9 C -0.02163(19) 0.6055(2) 0.77944(15) 0.0548(5) Uani 1 1 d . . . . .
C7 C -0.06374(19) 0.78202(19) 0.88461(17) 0.0527(4) Uani 1 1 d . . . . .
C1 C 0.2779(2) 0.66912(19) 0.96585(16) 0.0536(4) Uani 1 1 d . . . . .
H1 H 0.2040 0.7171 1.0077 0.064 Uiso 1 1 calc R . . . .
C11 C 0.6362(2) 0.73744(18) 0.54038(15) 0.0497(4) Uani 1 1 d . . . . .
H11 H 0.7267 0.7028 0.5014 0.060 Uiso 1 1 calc R . . . .
C19 C 0.3469(3) 0.6956(2) 0.36005(18) 0.0635(5) Uani 1 1 d . . . . .
C17 C 0.6325(3) 0.7120(2) 0.29726(15) 0.0624(6) Uani 1 1 d . . . . .
C15 C 0.3769(2) 0.7198(2) 0.62353(16) 0.0558(4) Uani 1 1 d . . . . .
H15 H 0.2846 0.6733 0.6416 0.067 Uiso 1 1 calc R . . . .
C12 C 0.6419(2) 0.85593(19) 0.57069(16) 0.0543(4) Uani 1 1 d . . . . .
C5 C 0.3431(2) 0.4944(2) 0.88165(16) 0.0561(4) Uani 1 1 d . . . . .
H5 H 0.3140 0.4192 0.8642 0.067 Uiso 1 1 calc R . . . .
C8 C -0.0470(2) 0.7413(2) 0.79115(18) 0.0629(5) Uani 1 1 d . . . . .
H8 H -0.0533 0.8114 0.7301 0.075 Uiso 1 1 calc R . . . .
C2 C 0.4283(2) 0.7110(2) 0.93084(17) 0.0580(5) Uani 1 1 d . . . . .
C4 C 0.4953(2) 0.5314(2) 0.84471(17) 0.0634(5) Uani 1 1 d . . . . .
H4 H 0.5674 0.4818 0.8031 0.076 Uiso 1 1 calc R . . . .
C18 C 0.4871(3) 0.7583(2) 0.29145(18) 0.0728(7) Uani 1 1 d . . . . .
H18 H 0.4832 0.8386 0.2366 0.087 Uiso 1 1 calc R . . . .
C13 C 0.5102(3) 0.9083(2) 0.63039(18) 0.0649(5) Uani 1 1 d . . . . .
H13 H 0.5123 0.9891 0.6511 0.078 Uiso 1 1 calc R . . . .
C3 C 0.5406(2) 0.6420(2) 0.86949(18) 0.0623(5) Uani 1 1 d . . . . .
H3 H 0.6432 0.6691 0.8457 0.075 Uiso 1 1 calc R . . . .
C14 C 0.3761(3) 0.8366(2) 0.65804(18) 0.0655(5) Uani 1 1 d . . . . .
H14 H 0.2850 0.8669 0.7000 0.079 Uiso 1 1 calc R . . . .
C10 C -0.0214(3) 0.5798(3) 0.67426(19) 0.0791(7) Uani 1 1 d . . . . .
H10A H 0.0542 0.5108 0.6566 0.119 Uiso 1 1 calc GR . . . .
H10B H 0.0026 0.6652 0.6169 0.119 Uiso 1 1 calc GR . . . .
H10C H -0.1209 0.5469 0.6825 0.119 Uiso 1 1 calc GR . . . .
C6 C -0.0931(3) 0.9339(2) 0.8823(2) 0.0849(7) Uani 1 1 d . . . . .
H6A H -0.1964 0.9443 0.9260 0.127 Uiso 1 1 calc GR . . . .
H6B H -0.0787 0.9890 0.8087 0.127 Uiso 1 1 calc GR . . . .
H6C H -0.0226 0.9650 0.9107 0.127 Uiso 1 1 calc GR . . . .
C20 C 0.1999(4) 0.7565(3) 0.3374(3) 0.1041(10) Uani 1 1 d . . . . .
H20A H 0.1143 0.6986 0.3872 0.156 Uiso 1 1 calc GR . . . .
H20B H 0.2064 0.7602 0.2642 0.156 Uiso 1 1 calc GR . . . .
H20C H 0.1860 0.8491 0.3465 0.156 Uiso 1 1 calc GR . . . .
C16 C 0.7720(4) 0.7966(3) 0.2193(2) 0.0977(10) Uani 1 1 d . . . . .
H16A H 0.8203 0.8344 0.2590 0.147 Uiso 1 1 calc GR . . . .
H16B H 0.7414 0.8715 0.1673 0.147 Uiso 1 1 calc GR . . . .
H16C H 0.8431 0.7376 0.1820 0.147 Uiso 1 1 calc GR . . . .


_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
Ni2 O3 2.0091(12) . ?
Ni2 O3 2.0091(12) 2_666 ?
Ni2 O4 2.0167(13) 2_666 ?
Ni2 O4 2.0167(13) . ?
Ni2 N2 2.1341(14) . ?
Ni2 N2 2.1341(14) 2_666 ?
Ni1 O1 2.0120(12) 2_567 ?
Ni1 O1 2.0119(12) . ?
Ni1 O2 2.0176(13) . ?
Ni1 O2 2.0176(13) 2_567 ?
Ni1 N1 2.1258(14) 2_567 ?
Ni1 N1 2.1258(14) . ?
Cl2 Cl2 3.4335(12) 2_776 ?
Cl2 C12 1.7342(19) . ?
Cl1 Cl1 3.4405(13) 2_677 ?
Cl1 C2 1.733(2) . ?
O1 C7 1.252(2) . ?
O3 C17 1.259(2) . ?
O2 C9 1.254(2) . ?
O4 C19 1.253(2) . ?
N2 C11 1.330(2) . ?
N2 C15 1.335(2) . ?
N1 C1 1.330(2) . ?
N1 C5 1.334(2) . ?
C9 C8 1.401(3) . ?
C9 C10 1.511(3) . ?
C7 C8 1.391(3) . ?
C7 C6 1.512(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.370(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.367(3) . ?
C19 C18 1.398(4) . ?
C19 C20 1.519(3) . ?
C17 C18 1.395(3) . ?
C17 C16 1.510(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.372(3) . ?
C12 C13 1.378(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.371(3) . ?
C8 H8 0.9300 . ?
C2 C3 1.374(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.371(3) . ?
C18 H18 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.368(3) . ?
C3 H3 0.9300 . ?
C14 H14 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
O3 Ni2 O3 180.0 . 2_666 ?
O3 Ni2 O4 91.33(6) 2_666 2_666 ?
O3 Ni2 O4 88.67(6) 2_666 . ?
O3 Ni2 O4 88.67(6) . 2_666 ?
O3 Ni2 O4 91.33(6) . . ?
O3 Ni2 N2 92.67(5) 2_666 . ?
O3 Ni2 N2 87.33(5) 2_666 2_666 ?
O3 Ni2 N2 92.67(5) . 2_666 ?
O3 Ni2 N2 87.33(5) . . ?
O4 Ni2 O4 180.00(4) 2_666 . ?
O4 Ni2 N2 90.55(6) . . ?
O4 Ni2 N2 89.45(6) 2_666 . ?
O4 Ni2 N2 90.55(6) 2_666 2_666 ?
O4 Ni2 N2 89.45(6) . 2_666 ?
N2 Ni2 N2 180.0 . 2_666 ?
O1 Ni1 O1 180.0 . 2_567 ?
O1 Ni1 O2 91.57(5) 2_567 2_567 ?
O1 Ni1 O2 88.43(5) 2_567 . ?
O1 Ni1 O2 91.57(5) . . ?
O1 Ni1 O2 88.43(5) . 2_567 ?
O1 Ni1 N1 88.72(5) . . ?
O1 Ni1 N1 91.28(5) . 2_567 ?
O1 Ni1 N1 88.72(5) 2_567 2_567 ?
O1 Ni1 N1 91.28(5) 2_567 . ?
O2 Ni1 O2 180.0 . 2_567 ?
O2 Ni1 N1 92.03(6) 2_567 2_567 ?
O2 Ni1 N1 87.97(6) 2_567 . ?
O2 Ni1 N1 92.03(6) . . ?
O2 Ni1 N1 87.97(6) . 2_567 ?
N1 Ni1 N1 180.0 . 2_567 ?
C12 Cl2 Cl2 170.14(8) . 2_776 ?
C2 Cl1 Cl1 173.11(9) . 2_677 ?
C7 O1 Ni1 124.95(13) . . ?
C17 O3 Ni2 123.93(14) . . ?
C9 O2 Ni1 125.03(13) . . ?
C19 O4 Ni2 124.30(14) . . ?
C11 N2 Ni2 119.90(12) . . ?
C11 N2 C15 118.05(16) . . ?
C15 N2 Ni2 121.82(12) . . ?
C1 N1 Ni1 120.02(12) . . ?
C1 N1 C5 117.99(16) . . ?
C5 N1 Ni1 121.99(13) . . ?
O2 C9 C8 125.39(19) . . ?
O2 C9 C10 115.7(2) . . ?
C8 C9 C10 118.9(2) . . ?
O1 C7 C8 125.78(18) . . ?
O1 C7 C6 115.0(2) . . ?
C8 C7 C6 119.17(19) . . ?
N1 C1 H1 119.1 . . ?
N1 C1 C2 121.75(17) . . ?
C2 C1 H1 119.1 . . ?
N2 C11 H11 119.1 . . ?
N2 C11 C12 121.86(17) . . ?
C12 C11 H11 119.1 . . ?
O4 C19 C18 125.9(2) . . ?
O4 C19 C20 115.3(2) . . ?
C18 C19 C20 118.9(2) . . ?
O3 C17 C18 125.48(19) . . ?
O3 C17 C16 115.3(2) . . ?
C18 C17 C16 119.2(2) . . ?
N2 C15 H15 118.7 . . ?
N2 C15 C14 122.64(18) . . ?
C14 C15 H15 118.7 . . ?
C11 C12 Cl2 119.09(15) . . ?
C11 C12 C13 120.45(18) . . ?
C13 C12 Cl2 120.44(16) . . ?
N1 C5 H5 118.6 . . ?
N1 C5 C4 122.77(18) . . ?
C4 C5 H5 118.6 . . ?
C9 C8 H8 116.6 . . ?
C7 C8 C9 126.72(18) . . ?
C7 C8 H8 116.6 . . ?
C1 C2 Cl1 118.95(16) . . ?
C1 C2 C3 120.69(18) . . ?
C3 C2 Cl1 120.37(16) . . ?
C5 C4 H4 120.2 . . ?
C5 C4 C3 119.57(18) . . ?
C3 C4 H4 120.2 . . ?
C19 C18 H18 116.8 . . ?
C17 C18 C19 126.31(19) . . ?
C17 C18 H18 116.8 . . ?
C12 C13 H13 121.3 . . ?
C14 C13 C12 117.39(19) . . ?
C14 C13 H13 121.3 . . ?
C2 C3 H3 121.4 . . ?
C4 C3 C2 117.24(18) . . ?
C4 C3 H3 121.4 . . ?
C15 C14 H14 120.2 . . ?
C13 C14 C15 119.58(19) . . ?
C13 C14 H14 120.2 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_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_3b
_database_code_depnum_ccdc_archive 'CCDC 1582540'
_audit_update_record             
;
2017-10-27 deposited with the CCDC.
2017-12-04 downloaded from the CCDC.
;
_audit_creation_date             2017-10-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H22 I2 N2 Ni O4'
_chemical_formula_sum            'C20 H22 I2 N2 Ni O4'
_chemical_formula_weight         666.90
_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'
I I -0.4742 1.8119 '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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.0225(2)
_cell_length_b                   9.6265(2)
_cell_length_c                   15.4896(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.406(2)
_cell_angle_gamma                90
_cell_volume                     1188.77(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8272
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      30.7610
_cell_measurement_theta_min      4.5340
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.439
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.863
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             644
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28298
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         4.421
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2291
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.669
_refine_diff_density_min         -1.319
_refine_diff_density_rms         0.140
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         2594
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0352
_refine_ls_restrained_S_all      1.067
_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)+(0.0471P)²+1.5724P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0921
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C3(H3), C4(H4), C8(H8)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
I1 I 0.84667(4) 0.05213(3) 0.71090(2) 0.06739(14) Uani 1 1 d . . . . .
Ni1 Ni 0.5000 0.5000 0.5000 0.03315(15) Uani 1 2 d S T P . .
O1 O 0.7098(3) 0.5660(3) 0.57131(15) 0.0422(5) Uani 1 1 d . . . . .
O2 O 0.5954(3) 0.5438(2) 0.38731(15) 0.0409(5) Uani 1 1 d . . . . .
N1 N 0.6005(3) 0.2961(3) 0.50230(17) 0.0391(6) Uani 1 1 d . . . . .
C2 C 0.7422(4) 0.1157(4) 0.5874(2) 0.0423(7) Uani 1 1 d . . . . .
C9 C 0.7273(4) 0.6132(4) 0.3834(2) 0.0427(7) Uani 1 1 d . . . . .
C1 C 0.6748(4) 0.2475(4) 0.5783(2) 0.0408(7) Uani 1 1 d . . . . .
H1 H 0.6810 0.3050 0.6268 0.049 Uiso 1 1 calc R . . . .
C5 C 0.5941(4) 0.2127(4) 0.4334(2) 0.0448(8) Uani 1 1 d . . . . .
H5 H 0.5431 0.2452 0.3804 0.054 Uiso 1 1 calc R . . . .
C7 C 0.8283(4) 0.6282(3) 0.5411(2) 0.0382(7) Uani 1 1 d . . . . .
C3 C 0.7341(6) 0.0301(4) 0.5154(3) 0.0538(9) Uani 1 1 d . . . . .
H3 H 0.7780 -0.0593 0.5196 0.065 Uiso 1 1 calc R . . . .
C4 C 0.6594(6) 0.0807(4) 0.4373(3) 0.0548(9) Uani 1 1 d . . . . .
H4 H 0.6533 0.0259 0.3876 0.066 Uiso 1 1 calc R . . . .
C8 C 0.8385(4) 0.6569(4) 0.4531(2) 0.0490(8) Uani 1 1 d . . . . .
H8 H 0.9288 0.7107 0.4402 0.059 Uiso 1 1 calc R . . . .
C6 C 0.9698(5) 0.6753(5) 0.6067(3) 0.0583(10) Uani 1 1 d . . . . .
H6A H 0.9269 0.7370 0.6476 0.088 Uiso 1 1 calc GR . . . .
H6B H 1.0525 0.7228 0.5775 0.088 Uiso 1 1 calc GR . . . .
H6C H 1.0201 0.5960 0.6369 0.088 Uiso 1 1 calc GR . . . .
C10 C 0.7676(7) 0.6493(7) 0.2928(3) 0.0801(16) Uani 1 1 d . . . . .
H10A H 0.7803 0.5654 0.2607 0.120 Uiso 1 1 calc GR . . . .
H10B H 0.8700 0.7016 0.2966 0.120 Uiso 1 1 calc GR . . . .
H10C H 0.6779 0.7037 0.2638 0.120 Uiso 1 1 calc GR . . . .


_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
I1 O1 3.456(2) 2_646 ?
I1 O2 3.329(2) 4_666 ?
I1 C2 2.092(3) . ?
Ni1 O1 2.011(2) 3_666 ?
Ni1 O1 2.011(2) . ?
Ni1 O2 2.027(2) 3_666 ?
Ni1 O2 2.027(2) . ?
Ni1 N1 2.121(3) 3_666 ?
Ni1 N1 2.121(3) . ?
O1 C7 1.257(4) . ?
O2 C9 1.259(4) . ?
N1 C1 1.343(4) . ?
N1 C5 1.332(5) . ?
C2 C1 1.380(5) . ?
C2 C3 1.382(5) . ?
C9 C8 1.387(5) . ?
C9 C10 1.515(5) . ?
C1 H1 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.373(6) . ?
C7 C8 1.401(5) . ?
C7 C6 1.506(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(6) . ?
C4 H4 0.9300 . ?
C8 H8 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 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
O2 I1 O1 48.81(5) 4_666 2_646 ?
C2 I1 O1 142.96(10) . 2_646 ?
C2 I1 O2 166.83(10) . 4_666 ?
O1 Ni1 O1 180.0 . 3_666 ?
O1 Ni1 O2 88.06(9) . 3_666 ?
O1 Ni1 O2 88.06(9) 3_666 . ?
O1 Ni1 O2 91.94(10) . . ?
O1 Ni1 O2 91.94(9) 3_666 3_666 ?
O1 Ni1 N1 89.41(10) . . ?
O1 Ni1 N1 90.59(10) . 3_666 ?
O1 Ni1 N1 90.59(10) 3_666 . ?
O1 Ni1 N1 89.41(10) 3_666 3_666 ?
O2 Ni1 O2 180.0 3_666 . ?
O2 Ni1 N1 88.43(10) . 3_666 ?
O2 Ni1 N1 91.57(10) . . ?
O2 Ni1 N1 88.43(10) 3_666 . ?
O2 Ni1 N1 91.57(10) 3_666 3_666 ?
N1 Ni1 N1 180.0 . 3_666 ?
C7 O1 Ni1 124.6(2) . . ?
C9 O2 Ni1 123.5(2) . . ?
C1 N1 Ni1 117.9(2) . . ?
C5 N1 Ni1 124.3(2) . . ?
C5 N1 C1 117.8(3) . . ?
C1 C2 I1 118.4(3) . . ?
C1 C2 C3 118.8(3) . . ?
C3 C2 I1 122.8(3) . . ?
O2 C9 C8 126.5(3) . . ?
O2 C9 C10 115.7(3) . . ?
C8 C9 C10 117.8(3) . . ?
N1 C1 C2 122.7(3) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
N1 C5 H5 118.6 . . ?
N1 C5 C4 122.8(3) . . ?
C4 C5 H5 118.6 . . ?
O1 C7 C8 125.8(3) . . ?
O1 C7 C6 115.9(3) . . ?
C8 C7 C6 118.4(3) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 C2 118.3(4) . . ?
C4 C3 H3 120.8 . . ?
C5 C4 C3 119.5(4) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C9 C8 C7 126.5(3) . . ?
C9 C8 H8 116.7 . . ?
C7 C8 H8 116.7 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_olex2_date_sample_data_collection 2017-01-02
_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_6b
_database_code_depnum_ccdc_archive 'CCDC 1582543'
_audit_update_record             
;
2017-10-27 deposited with the CCDC.
2017-12-04 downloaded from the CCDC.
;
_audit_creation_date             2017-10-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H20 I2 N4 Ni O4'
_chemical_formula_sum            'C18 H20 I2 N4 Ni O4'
_chemical_formula_weight         668.89
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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                   6.3490(3)
_cell_length_b                   9.2589(5)
_cell_length_c                   10.2457(4)
_cell_angle_alpha                102.659(5)
_cell_angle_beta                 100.162(4)
_cell_angle_gamma                98.163(4)
_cell_volume                     568.11(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2347
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      31.7240
_cell_measurement_theta_min      5.0780
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.601
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light blue'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.955
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             322
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4563
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_min         4.149
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2139
_reflns_number_total             2476
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    ?
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.580
_refine_diff_density_min         -0.911
_refine_diff_density_rms         0.080
_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     135
_refine_ls_number_reflns         2476
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0287
_refine_ls_restrained_S_all      1.065
_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)+(0.0259P)²+0.2987P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0623
_refine_ls_wR_factor_ref         0.0662
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C7(H7), C3(H3)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
I1 I 0.49138(4) 0.78627(3) 0.02676(2) 0.06575(11) Uani 1 1 d . . . . .
Ni1 Ni 0.5000 0.5000 0.5000 0.03766(13) Uani 1 2 d S T P . .
O1 O 0.3242(3) 0.6613(2) 0.4886(2) 0.0454(5) Uani 1 1 d . . . . .
O2 O 0.7378(3) 0.6432(3) 0.6469(2) 0.0484(5) Uani 1 1 d . . . . .
N1 N 0.6537(4) 0.5578(3) 0.3406(2) 0.0411(5) Uani 1 1 d . . . . .
N2 N 0.8292(5) 0.6247(4) 0.1254(3) 0.0573(7) Uani 1 1 d . . . . .
C6 C 0.3749(5) 0.7939(4) 0.5643(3) 0.0464(7) Uani 1 1 d . . . . .
C2 C 0.6488(5) 0.6669(3) 0.1534(3) 0.0431(6) Uani 1 1 d . . . . .
C1 C 0.5597(5) 0.6351(3) 0.2591(3) 0.0437(7) Uani 1 1 d . . . . .
H1 H 0.4322 0.6679 0.2739 0.052 Uiso 1 1 calc R . . . .
C4 C 0.8362(5) 0.5151(4) 0.3144(3) 0.0494(7) Uani 1 1 d . . . . .
H4 H 0.9077 0.4618 0.3695 0.059 Uiso 1 1 calc R . . . .
C8 C 0.7301(5) 0.7770(4) 0.7015(3) 0.0484(7) Uani 1 1 d . . . . .
C7 C 0.5605(6) 0.8517(4) 0.6674(4) 0.0558(8) Uani 1 1 d . . . . .
H7 H 0.5730 0.9499 0.7187 0.067 Uiso 1 1 calc R . . . .
C3 C 0.9219(5) 0.5478(4) 0.2076(4) 0.0594(9) Uani 1 1 d . . . . .
H3 H 1.0493 0.5150 0.1924 0.071 Uiso 1 1 calc R . . . .
C5 C 0.2127(7) 0.8940(4) 0.5351(4) 0.0686(10) Uani 1 1 d . . . . .
H5A H 0.2226 0.9203 0.4506 0.103 Uiso 1 1 calc GR . . . .
H5B H 0.2447 0.9840 0.6083 0.103 Uiso 1 1 calc GR . . . .
H5C H 0.0681 0.8413 0.5282 0.103 Uiso 1 1 calc GR . . . .
C9 C 0.9235(7) 0.8610(5) 0.8144(4) 0.0772(12) Uani 1 1 d . . . . .
H9A H 0.9286 0.8160 0.8905 0.116 Uiso 1 1 calc GR . . . .
H9B H 0.9098 0.9645 0.8433 0.116 Uiso 1 1 calc GR . . . .
H9C H 1.0551 0.8559 0.7810 0.116 Uiso 1 1 calc GR . . . .


_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
I1 C2 2.095(3) . ?
Ni1 O1 1.9983(19) 2_666 ?
Ni1 O1 1.9984(19) . ?
Ni1 O2 2.014(2) 2_666 ?
Ni1 O2 2.014(2) . ?
Ni1 N1 2.169(2) 2_666 ?
Ni1 N1 2.169(2) . ?
O1 C6 1.263(4) . ?
O2 C8 1.255(4) . ?
N1 C1 1.331(4) . ?
N1 C4 1.329(4) . ?
N2 C2 1.320(4) . ?
N2 C3 1.330(4) . ?
C6 C7 1.388(5) . ?
C6 C5 1.514(4) . ?
C2 C1 1.374(4) . ?
C1 H1 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.376(5) . ?
C8 C7 1.394(5) . ?
C8 C9 1.511(5) . ?
C7 H7 0.9300 . ?
C3 H3 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 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
O1 Ni1 O1 180.00(9) 2_666 . ?
O1 Ni1 O2 88.24(9) . 2_666 ?
O1 Ni1 O2 91.76(9) . . ?
O1 Ni1 O2 91.76(9) 2_666 2_666 ?
O1 Ni1 O2 88.24(9) 2_666 . ?
O1 Ni1 N1 90.35(9) . 2_666 ?
O1 Ni1 N1 89.65(9) . . ?
O1 Ni1 N1 90.35(9) 2_666 . ?
O1 Ni1 N1 89.65(9) 2_666 2_666 ?
O2 Ni1 O2 180.00(10) 2_666 . ?
O2 Ni1 N1 88.70(9) . 2_666 ?
O2 Ni1 N1 91.30(9) 2_666 2_666 ?
O2 Ni1 N1 91.30(9) . . ?
O2 Ni1 N1 88.70(9) 2_666 . ?
N1 Ni1 N1 180.0 2_666 . ?
C6 O1 Ni1 124.98(19) . . ?
C8 O2 Ni1 124.9(2) . . ?
C1 N1 Ni1 119.84(19) . . ?
C4 N1 Ni1 123.6(2) . . ?
C4 N1 C1 116.5(3) . . ?
C2 N2 C3 115.2(3) . . ?
O1 C6 C7 126.0(3) . . ?
O1 C6 C5 114.5(3) . . ?
C7 C6 C5 119.5(3) . . ?
N2 C2 I1 117.3(2) . . ?
N2 C2 C1 123.5(3) . . ?
C1 C2 I1 119.2(2) . . ?
N1 C1 C2 120.9(3) . . ?
N1 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
N1 C4 H4 119.2 . . ?
N1 C4 C3 121.6(3) . . ?
C3 C4 H4 119.2 . . ?
O2 C8 C7 125.7(3) . . ?
O2 C8 C9 115.6(3) . . ?
C7 C8 C9 118.7(3) . . ?
C6 C7 C8 126.4(3) . . ?
C6 C7 H7 116.8 . . ?
C8 C7 H7 116.8 . . ?
N2 C3 C4 122.4(3) . . ?
N2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C6 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4 O2 0.93 2.59 3.259(4) 129.0 2_766
C3 H3 O2 0.93 2.74 3.335(4) 122.5 2_766

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
I1 C2 C1 N1 179.1(2) . . . . ?
Ni1 O1 C6 C7 0.5(4) . . . . ?
Ni1 O1 C6 C5 -179.6(2) . . . . ?
Ni1 O2 C8 C7 -2.4(4) . . . . ?
Ni1 O2 C8 C9 177.2(2) . . . . ?
Ni1 N1 C1 C2 -177.0(2) . . . . ?
Ni1 N1 C4 C3 176.6(3) . . . . ?
O1 C6 C7 C8 3.6(5) . . . . ?
O2 C8 C7 C6 -2.6(6) . . . . ?
N1 C4 C3 N2 0.6(6) . . . . ?
N2 C2 C1 N1 0.0(5) . . . . ?
C2 N2 C3 C4 -0.2(5) . . . . ?
C1 N1 C4 C3 -0.7(5) . . . . ?
C4 N1 C1 C2 0.4(4) . . . . ?
C3 N2 C2 I1 -179.3(2) . . . . ?
C3 N2 C2 C1 -0.1(5) . . . . ?
C5 C6 C7 C8 -176.2(3) . . . . ?
C9 C8 C7 C6 177.8(3) . . . . ?

_olex2_date_sample_data_collection 2016-02-13
_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_3a
_database_code_depnum_ccdc_archive 'CCDC 1582542'
_audit_update_record             
;
2017-10-27 deposited with the CCDC.
2017-12-04 downloaded from the CCDC.
;
_audit_creation_date             2017-10-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H22 Co I2 N2 O4'
_chemical_formula_sum            'C20 H22 Co I2 N2 O4'
_chemical_formula_weight         667.12
_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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.9717(5)
_cell_length_b                   9.7058(4)
_cell_length_c                   15.4552(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.710(4)
_cell_angle_gamma                90
_cell_volume                     1187.60(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1660
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      28.7180
_cell_measurement_theta_min      4.9200
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.348
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.866
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             642
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5140
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         4.405
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1993
_reflns_number_total             2583
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    ?
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.551
_refine_diff_density_min         -1.024
_refine_diff_density_rms         0.143
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         2583
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0423
_refine_ls_restrained_S_all      1.066
_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)+(0.0603P)²+0.2075P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1168
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C4(H4), C3(H3), C8(H8)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
I1 I 0.15263(5) 0.04780(4) 0.28952(2) 0.07475(19) Uani 1 1 d . . . . .
Co1 Co 0.5000 0.5000 0.5000 0.0387(2) Uani 1 2 d S T P . .
O2 O 0.3997(4) 0.5457(3) 0.61229(17) 0.0459(7) Uani 1 1 d . . . . .
O1 O 0.2845(4) 0.5618(3) 0.42895(18) 0.0468(7) Uani 1 1 d . . . . .
N1 N 0.4009(4) 0.2897(4) 0.4983(2) 0.0452(8) Uani 1 1 d . . . . .
C1 C 0.3267(5) 0.2419(5) 0.4223(3) 0.0466(10) Uani 1 1 d . . . . .
H1 H 0.3210 0.2988 0.3737 0.056 Uiso 1 1 calc R . . . .
C5 C 0.4065(6) 0.2079(5) 0.5669(3) 0.0511(10) Uani 1 1 d . . . . .
H5 H 0.4585 0.2400 0.6201 0.061 Uiso 1 1 calc R . . . .
C2 C 0.2581(5) 0.1116(5) 0.4132(3) 0.0476(10) Uani 1 1 d . . . . .
C9 C 0.2700(5) 0.6165(5) 0.6152(3) 0.0492(10) Uani 1 1 d . . . . .
C7 C 0.1673(5) 0.6263(4) 0.4578(3) 0.0447(9) Uani 1 1 d . . . . .
C4 C 0.3387(7) 0.0772(6) 0.5633(3) 0.0631(13) Uani 1 1 d . . . . .
H4 H 0.3432 0.0237 0.6135 0.076 Uiso 1 1 calc R . . . .
C3 C 0.2649(7) 0.0268(5) 0.4858(3) 0.0610(12) Uani 1 1 d . . . . .
H3 H 0.2205 -0.0619 0.4816 0.073 Uiso 1 1 calc R . . . .
C8 C 0.1580(6) 0.6585(5) 0.5450(3) 0.0547(11) Uani 1 1 d . . . . .
H8 H 0.0681 0.7135 0.5572 0.066 Uiso 1 1 calc R . . . .
C6 C 0.0253(6) 0.6727(6) 0.3911(3) 0.0639(13) Uani 1 1 d . . . . .
H6A H 0.0709 0.7226 0.3456 0.096 Uiso 1 1 calc GR . . . .
H6B H -0.0500 0.7313 0.4185 0.096 Uiso 1 1 calc GR . . . .
H6C H -0.0355 0.5937 0.3668 0.096 Uiso 1 1 calc GR . . . .
C10 C 0.2309(8) 0.6560(8) 0.7056(3) 0.089(2) Uani 1 1 d . . . . .
H10A H 0.2172 0.5741 0.7389 0.133 Uiso 1 1 calc GR . . . .
H10B H 0.1285 0.7089 0.7011 0.133 Uiso 1 1 calc GR . . . .
H10C H 0.3221 0.7099 0.7340 0.133 Uiso 1 1 calc GR . . . .


_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
I1 O2 3.332(3) 4_565 ?
I1 O1 3.473(3) 2_545 ?
I1 C2 2.090(4) . ?
Co1 O2 2.042(3) 3_666 ?
Co1 O2 2.042(3) . ?
Co1 O1 2.019(3) 3_666 ?
Co1 O1 2.019(3) . ?
Co1 N1 2.188(4) 3_666 ?
Co1 N1 2.188(4) . ?
O2 C9 1.247(5) . ?
O1 C7 1.250(5) . ?
N1 C1 1.334(5) . ?
N1 C5 1.321(6) . ?
C1 H1 0.9300 . ?
C1 C2 1.379(6) . ?
C5 H5 0.9300 . ?
C5 C4 1.377(7) . ?
C2 C3 1.387(7) . ?
C9 C8 1.383(6) . ?
C9 C10 1.516(6) . ?
C7 C8 1.394(6) . ?
C7 C6 1.509(6) . ?
C4 H4 0.9300 . ?
C4 C3 1.363(7) . ?
C3 H3 0.9300 . ?
C8 H8 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 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
O2 I1 O1 49.73(7) 4_565 2_545 ?
C2 I1 O2 166.58(12) . 4_565 ?
C2 I1 O1 142.10(13) . 2_545 ?
O2 Co1 O2 180.0 . 3_666 ?
O2 Co1 N1 92.06(12) 3_666 3_666 ?
O2 Co1 N1 87.94(12) 3_666 . ?
O2 Co1 N1 87.94(12) . 3_666 ?
O2 Co1 N1 92.06(12) . . ?
O1 Co1 O2 89.71(12) 3_666 . ?
O1 Co1 O2 89.71(12) . 3_666 ?
O1 Co1 O2 90.29(12) . . ?
O1 Co1 O2 90.29(12) 3_666 3_666 ?
O1 Co1 O1 180.0 . 3_666 ?
O1 Co1 N1 89.29(13) . . ?
O1 Co1 N1 90.71(12) 3_666 . ?
O1 Co1 N1 89.29(13) 3_666 3_666 ?
O1 Co1 N1 90.71(12) . 3_666 ?
N1 Co1 N1 180.0 3_666 . ?
C9 O2 Co1 124.0(3) . . ?
C7 O1 Co1 125.4(3) . . ?
C1 N1 Co1 117.2(3) . . ?
C5 N1 Co1 124.9(3) . . ?
C5 N1 C1 117.9(4) . . ?
N1 C1 H1 118.7 . . ?
N1 C1 C2 122.6(4) . . ?
C2 C1 H1 118.7 . . ?
N1 C5 H5 118.5 . . ?
N1 C5 C4 123.0(4) . . ?
C4 C5 H5 118.5 . . ?
C1 C2 I1 118.6(3) . . ?
C1 C2 C3 118.9(4) . . ?
C3 C2 I1 122.5(3) . . ?
O2 C9 C8 126.6(4) . . ?
O2 C9 C10 115.7(4) . . ?
C8 C9 C10 117.7(4) . . ?
O1 C7 C8 125.8(4) . . ?
O1 C7 C6 116.0(4) . . ?
C8 C7 C6 118.3(4) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 C5 119.5(5) . . ?
C3 C4 H4 120.2 . . ?
C2 C3 H3 121.0 . . ?
C4 C3 C2 118.1(5) . . ?
C4 C3 H3 121.0 . . ?
C9 C8 C7 126.1(4) . . ?
C9 C8 H8 116.9 . . ?
C7 C8 H8 116.9 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_olex2_date_sample_data_collection 2016-07-21
_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_6a
_database_code_depnum_ccdc_archive 'CCDC 1582549'
_audit_update_record             
;
2017-10-27 deposited with the CCDC.
2017-12-04 downloaded from the CCDC.
;
_audit_creation_date             2017-10-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H20 Co I2 N4 O4'
_chemical_formula_sum            'C18 H20 Co I2 N4 O4'
_chemical_formula_weight         669.11
_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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.3513(9)
_cell_length_b                   9.2560(11)
_cell_length_c                   10.3631(8)
_cell_angle_alpha                102.241(8)
_cell_angle_beta                 100.737(9)
_cell_angle_gamma                98.708(11)
_cell_volume                     573.27(12)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1521
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      29.3730
_cell_measurement_theta_min      4.4190
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.471
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark orange'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.938
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             321
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4009
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         4.271
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1748
_reflns_number_total             2226
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    ?
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.954
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         2226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0329
_refine_ls_restrained_S_all      1.046
_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)+(0.0391P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0848
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C3(H3), C7(H7)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
I1 I 0.50385(5) 0.21152(4) 0.97343(3) 0.07043(16) Uani 1 1 d . . . . .
Co1 Co 0.5000 0.5000 0.5000 0.0415(2) Uani 1 2 d S T P . .
O1 O 0.3269(4) 0.6640(3) 0.4866(3) 0.0504(7) Uani 1 1 d . . . . .
O2 O 0.7383(4) 0.6491(3) 0.6457(3) 0.0518(7) Uani 1 1 d . . . . .
N1 N 0.3415(5) 0.4428(4) 0.6628(3) 0.0464(8) Uani 1 1 d . . . . .
N2 N 0.1697(6) 0.3771(5) 0.8770(4) 0.0615(10) Uani 1 1 d . . . . .
C1 C 0.4337(6) 0.3649(5) 0.7442(4) 0.0469(9) Uani 1 1 d . . . . .
H1 H 0.5605 0.3318 0.7297 0.056 Uiso 1 1 calc R . . . .
C2 C 0.3472(6) 0.3321(5) 0.8486(4) 0.0474(9) Uani 1 1 d . . . . .
C6 C 0.3723(7) 0.7947(5) 0.5625(4) 0.0492(10) Uani 1 1 d . . . . .
C4 C 0.1614(6) 0.4871(5) 0.6904(4) 0.0527(10) Uani 1 1 d . . . . .
H4 H 0.0903 0.5418 0.6367 0.063 Uiso 1 1 calc R . . . .
C8 C 0.7294(7) 0.7814(5) 0.7010(4) 0.0525(10) Uani 1 1 d . . . . .
C3 C 0.0780(7) 0.4542(6) 0.7958(5) 0.0653(13) Uani 1 1 d . . . . .
H3 H -0.0484 0.4874 0.8110 0.078 Uiso 1 1 calc R . . . .
C7 C 0.5564(7) 0.8536(5) 0.6667(4) 0.0584(11) Uani 1 1 d . . . . .
H7 H 0.5659 0.9504 0.7190 0.070 Uiso 1 1 calc R . . . .
C5 C 0.2061(8) 0.8924(6) 0.5324(5) 0.0776(15) Uani 1 1 d . . . . .
H5A H 0.2089 0.9147 0.4463 0.116 Uiso 1 1 calc GR . . . .
H5B H 0.2419 0.9847 0.6020 0.116 Uiso 1 1 calc GR . . . .
H5C H 0.0627 0.8394 0.5299 0.116 Uiso 1 1 calc GR . . . .
C9 C 0.9224(8) 0.8670(7) 0.8135(5) 0.0816(16) Uani 1 1 d . . . . .
H9A H 0.9212 0.8268 0.8916 0.122 Uiso 1 1 calc GR . . . .
H9B H 0.9137 0.9717 0.8366 0.122 Uiso 1 1 calc GR . . . .
H9C H 1.0554 0.8570 0.7841 0.122 Uiso 1 1 calc GR . . . .


_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
I1 C2 2.093(4) . ?
Co1 O1 2.018(2) . ?
Co1 O1 2.018(2) 2_666 ?
Co1 O2 2.026(3) . ?
Co1 O2 2.026(3) 2_666 ?
Co1 N1 2.233(3) . ?
Co1 N1 2.233(3) 2_666 ?
O1 C6 1.254(5) . ?
O2 C8 1.252(5) . ?
N1 C1 1.333(5) . ?
N1 C4 1.332(5) . ?
N2 C2 1.321(5) . ?
N2 C3 1.325(6) . ?
C1 H1 0.9300 . ?
C1 C2 1.369(6) . ?
C6 C7 1.385(6) . ?
C6 C5 1.521(5) . ?
C4 H4 0.9300 . ?
C4 C3 1.368(6) . ?
C8 C7 1.399(6) . ?
C8 C9 1.508(6) . ?
C3 H3 0.9300 . ?
C7 H7 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 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
O1 Co1 O1 180.0 . 2_666 ?
O1 Co1 O2 90.09(11) 2_666 . ?
O1 Co1 O2 89.91(11) 2_666 2_666 ?
O1 Co1 O2 89.91(11) . . ?
O1 Co1 O2 90.08(11) . 2_666 ?
O1 Co1 N1 89.66(11) 2_666 . ?
O1 Co1 N1 90.34(11) 2_666 2_666 ?
O1 Co1 N1 89.66(11) . 2_666 ?
O1 Co1 N1 90.34(11) . . ?
O2 Co1 O2 180.00(13) . 2_666 ?
O2 Co1 N1 91.36(12) 2_666 . ?
O2 Co1 N1 88.64(12) . . ?
O2 Co1 N1 88.64(12) 2_666 2_666 ?
O2 Co1 N1 91.36(12) . 2_666 ?
N1 Co1 N1 180.0 . 2_666 ?
C6 O1 Co1 126.3(2) . . ?
C8 O2 Co1 126.1(3) . . ?
C1 N1 Co1 119.8(3) . . ?
C4 N1 Co1 124.6(3) . . ?
C4 N1 C1 115.6(3) . . ?
C2 N2 C3 115.3(4) . . ?
N1 C1 H1 119.0 . . ?
N1 C1 C2 121.9(4) . . ?
C2 C1 H1 119.0 . . ?
N2 C2 I1 117.7(3) . . ?
N2 C2 C1 122.7(4) . . ?
C1 C2 I1 119.6(3) . . ?
O1 C6 C7 125.6(4) . . ?
O1 C6 C5 114.8(4) . . ?
C7 C6 C5 119.6(4) . . ?
N1 C4 H4 119.1 . . ?
N1 C4 C3 121.7(4) . . ?
C3 C4 H4 119.1 . . ?
O2 C8 C7 125.3(4) . . ?
O2 C8 C9 116.1(4) . . ?
C7 C8 C9 118.6(4) . . ?
N2 C3 C4 122.8(4) . . ?
N2 C3 H3 118.6 . . ?
C4 C3 H3 118.6 . . ?
C6 C7 C8 126.2(4) . . ?
C6 C7 H7 116.9 . . ?
C8 C7 H7 116.9 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C6 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4 O2 0.93 2.59 3.276(5) 131.1 1_455
C3 H3 O2 0.93 2.80 3.383(5) 121.7 1_455

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 O1 C6 C7 3.1(6) . . . . ?
Co1 O1 C6 C5 -177.3(3) . . . . ?
Co1 O2 C8 C7 -3.7(6) . . . . ?
Co1 O2 C8 C9 176.1(3) . . . . ?
Co1 N1 C1 C2 177.5(3) . . . . ?
Co1 N1 C4 C3 -176.9(4) . . . . ?
O1 C6 C7 C8 3.8(8) . . . . ?
O2 C8 C7 C6 -3.5(8) . . . . ?
N1 C1 C2 I1 -179.2(3) . . . . ?
N1 C1 C2 N2 -1.1(7) . . . . ?
N1 C4 C3 N2 0.1(8) . . . . ?
C1 N1 C4 C3 0.1(6) . . . . ?
C2 N2 C3 C4 -0.7(7) . . . . ?
C4 N1 C1 C2 0.4(6) . . . . ?
C3 N2 C2 I1 179.4(3) . . . . ?
C3 N2 C2 C1 1.2(6) . . . . ?
C5 C6 C7 C8 -175.8(4) . . . . ?
C9 C8 C7 C6 176.8(4) . . . . ?

_olex2_date_sample_data_collection 2016-02-09
_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_1a
_database_code_depnum_ccdc_archive 'CCDC 1582547'
_audit_update_record             
;
2017-10-27 deposited with the CCDC.
2017-12-04 downloaded from the CCDC.
;
_audit_creation_date             2017-10-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H22 Cl2 Co N2 O4'
_chemical_formula_sum            'C20 H22 Cl2 Co N2 O4'
_chemical_formula_weight         484.22
_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'
O O 0.0106 0.0060 '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                   9.0807(5)
_cell_length_b                   10.2369(6)
_cell_length_c                   13.0194(8)
_cell_angle_alpha                74.910(5)
_cell_angle_beta                 74.027(5)
_cell_angle_gamma                86.362(5)
_cell_volume                     1123.37(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3348
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      29.3080
_cell_measurement_theta_min      4.6550
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.029
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87377
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark orange'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             498
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9149
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         4.370
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  template
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3549
_reflns_number_total             4395
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         4395
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0341
_refine_ls_restrained_S_all      1.027
_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)+(0.0396P)²+0.2828P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0890
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C5(H5), C1(H1), C15(H15), C4(H4), C3(H3), C13(H13), C14(H14),
 C18(H18), C8(H8)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C6(H6A,H6B,H6C), C16(H16A,H16B,H16C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Co2 Co 0.5000 0.5000 0.5000 0.04582(12) Uani 1 2 d S T P . .
Co1 Co 0.0000 0.5000 1.0000 0.04912(13) Uani 1 2 d S T P . .
Cl2 Cl 0.81629(9) 0.94679(7) 0.53202(8) 0.0924(3) Uani 1 1 d . . . . .
Cl1 Cl 0.48063(11) 0.86049(9) 0.95817(9) 0.1111(3) Uani 1 1 d . . . . .
O3 O 0.66288(17) 0.59791(14) 0.36507(13) 0.0564(4) Uani 1 1 d . . . . .
O2 O -0.01049(18) 0.50124(15) 0.84556(13) 0.0603(4) Uani 1 1 d . . . . .
O1 O -0.06047(18) 0.69778(14) 0.97264(13) 0.0584(4) Uani 1 1 d . . . . .
O4 O 0.33612(17) 0.59212(14) 0.42651(14) 0.0592(4) Uani 1 1 d . . . . .
N2 N 0.50595(19) 0.67597(16) 0.56685(15) 0.0493(4) Uani 1 1 d . . . . .
N1 N 0.2405(2) 0.56549(17) 0.93933(15) 0.0509(4) Uani 1 1 d . . . . .
C7 C -0.0578(2) 0.7756(2) 0.8801(2) 0.0555(6) Uani 1 1 d . . . . .
C9 C -0.0211(2) 0.6045(2) 0.7704(2) 0.0564(6) Uani 1 1 d . . . . .
C17 C 0.6422(3) 0.7063(2) 0.29770(19) 0.0594(6) Uani 1 1 d . . . . .
C11 C 0.6368(2) 0.7431(2) 0.54301(18) 0.0514(5) Uani 1 1 d . . . . .
H11 H 0.7268 0.7088 0.5053 0.062 Uiso 1 1 calc R . . . .
C19 C 0.3577(3) 0.6970(2) 0.3476(2) 0.0628(6) Uani 1 1 d . . . . .
C5 C 0.3481(3) 0.4975(2) 0.88240(19) 0.0569(6) Uani 1 1 d . . . . .
H5 H 0.3191 0.4212 0.8663 0.068 Uiso 1 1 calc R . . . .
C1 C 0.2845(3) 0.6744(2) 0.96145(19) 0.0559(5) Uani 1 1 d . . . . .
H1 H 0.2113 0.7233 1.0014 0.067 Uiso 1 1 calc R . . . .
C12 C 0.6427(3) 0.8611(2) 0.5724(2) 0.0566(6) Uani 1 1 d . . . . .
C15 C 0.3795(3) 0.7248(2) 0.62412(19) 0.0559(5) Uani 1 1 d . . . . .
H15 H 0.2879 0.6775 0.6427 0.067 Uiso 1 1 calc R . . . .
C2 C 0.4343(3) 0.7166(2) 0.9271(2) 0.0597(6) Uani 1 1 d . . . . .
C4 C 0.4994(3) 0.5346(2) 0.8465(2) 0.0625(6) Uani 1 1 d . . . . .
H4 H 0.5709 0.4841 0.8070 0.075 Uiso 1 1 calc R . . . .
C3 C 0.5451(3) 0.6467(3) 0.8690(2) 0.0636(6) Uani 1 1 d . . . . .
H3 H 0.6473 0.6740 0.8457 0.076 Uiso 1 1 calc R . . . .
C13 C 0.5125(3) 0.9123(2) 0.6302(2) 0.0674(7) Uani 1 1 d . . . . .
H13 H 0.5150 0.9925 0.6506 0.081 Uiso 1 1 calc R . . . .
C14 C 0.3788(3) 0.8416(2) 0.6568(2) 0.0650(6) Uani 1 1 d . . . . .
H14 H 0.2882 0.8725 0.6968 0.078 Uiso 1 1 calc R . . . .
C18 C 0.4998(3) 0.7561(2) 0.2867(2) 0.0664(7) Uani 1 1 d . . . . .
H18 H 0.4992 0.8367 0.2335 0.080 Uiso 1 1 calc R . . . .
C8 C -0.0374(3) 0.7374(2) 0.7828(2) 0.0630(6) Uani 1 1 d . . . . .
H8 H -0.0342 0.8063 0.7195 0.076 Uiso 1 1 calc R . . . .
C10 C -0.0170(3) 0.5805(3) 0.6602(2) 0.0783(8) Uani 1 1 d . . . . .
H10A H 0.0615 0.5163 0.6425 0.117 Uiso 1 1 calc GR . . . .
H10B H 0.0046 0.6642 0.6042 0.117 Uiso 1 1 calc GR . . . .
H10C H -0.1144 0.5456 0.6637 0.117 Uiso 1 1 calc GR . . . .
C6 C -0.0791(4) 0.9240(2) 0.8784(3) 0.0883(9) Uani 1 1 d . . . . .
H6A H -0.1780 0.9368 0.9252 0.132 Uiso 1 1 calc GR . . . .
H6B H -0.0717 0.9761 0.8042 0.132 Uiso 1 1 calc GR . . . .
H6C H -0.0010 0.9532 0.9046 0.132 Uiso 1 1 calc GR . . . .
C16 C 0.7853(4) 0.7842(3) 0.2257(2) 0.0899(10) Uani 1 1 d . . . . .
H16A H 0.8311 0.8215 0.2702 0.135 Uiso 1 1 calc GR . . . .
H16B H 0.7595 0.8560 0.1697 0.135 Uiso 1 1 calc GR . . . .
H16C H 0.8564 0.7245 0.1916 0.135 Uiso 1 1 calc GR . . . .
C20 C 0.2149(4) 0.7607(3) 0.3176(3) 0.1025(11) Uani 1 1 d . . . . .
H20A H 0.1916 0.7199 0.2653 0.154 Uiso 1 1 calc GR . . . .
H20B H 0.2320 0.8561 0.2857 0.154 Uiso 1 1 calc GR . . . .
H20C H 0.1306 0.7466 0.3829 0.154 Uiso 1 1 calc GR . . . .


_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
Co2 O3 2.0297(14) . ?
Co2 O3 2.0297(14) 2_666 ?
Co2 O4 2.0384(15) . ?
Co2 O4 2.0383(15) 2_666 ?
Co2 N2 2.2046(16) 2_666 ?
Co2 N2 2.2046(16) . ?
Co1 O2 2.0357(16) 2_567 ?
Co1 O2 2.0357(16) . ?
Co1 O1 2.0295(14) . ?
Co1 O1 2.0294(14) 2_567 ?
Co1 N1 2.1916(17) . ?
Co1 N1 2.1916(17) 2_567 ?
Cl2 Cl2 3.3869(14) 2_776 ?
Cl2 C12 1.734(2) . ?
Cl1 Cl1 3.3804(14) 2_677 ?
Cl1 C2 1.730(2) . ?
O3 C17 1.262(3) . ?
O2 C9 1.259(3) . ?
O1 C7 1.255(3) . ?
O4 C19 1.260(3) . ?
N2 C11 1.330(3) . ?
N2 C15 1.332(3) . ?
N1 C5 1.331(3) . ?
N1 C1 1.331(3) . ?
C7 C8 1.382(4) . ?
C7 C6 1.514(3) . ?
C9 C8 1.406(3) . ?
C9 C10 1.507(4) . ?
C17 C18 1.390(4) . ?
C17 C16 1.508(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.367(3) . ?
C19 C18 1.395(4) . ?
C19 C20 1.516(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.368(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.370(3) . ?
C12 C13 1.369(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.369(3) . ?
C2 C3 1.367(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.370(3) . ?
C3 H3 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.367(3) . ?
C14 H14 0.9300 . ?
C18 H18 0.9300 . ?
C8 H8 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
O3 Co2 O3 180.0 . 2_666 ?
O3 Co2 O4 89.06(6) 2_666 2_666 ?
O3 Co2 O4 90.94(6) 2_666 . ?
O3 Co2 O4 90.94(6) . 2_666 ?
O3 Co2 O4 89.06(6) . . ?
O3 Co2 N2 93.33(6) 2_666 . ?
O3 Co2 N2 86.67(6) 2_666 2_666 ?
O3 Co2 N2 93.34(6) . 2_666 ?
O3 Co2 N2 86.67(6) . . ?
O4 Co2 O4 180.0 2_666 . ?
O4 Co2 N2 90.17(6) 2_666 . ?
O4 Co2 N2 90.17(6) . 2_666 ?
O4 Co2 N2 89.83(6) 2_666 2_666 ?
O4 Co2 N2 89.83(6) . . ?
N2 Co2 N2 180.0 . 2_666 ?
O2 Co1 O2 180.0 . 2_567 ?
O2 Co1 N1 91.99(7) 2_567 2_567 ?
O2 Co1 N1 88.01(7) 2_567 . ?
O2 Co1 N1 91.99(7) . . ?
O2 Co1 N1 88.01(7) . 2_567 ?
O1 Co1 O2 90.47(6) 2_567 . ?
O1 Co1 O2 90.47(6) . 2_567 ?
O1 Co1 O2 89.53(6) . . ?
O1 Co1 O2 89.53(6) 2_567 2_567 ?
O1 Co1 O1 180.00(10) 2_567 . ?
O1 Co1 N1 91.59(6) 2_567 . ?
O1 Co1 N1 88.41(6) . . ?
O1 Co1 N1 88.41(6) 2_567 2_567 ?
O1 Co1 N1 91.59(6) . 2_567 ?
N1 Co1 N1 180.0 . 2_567 ?
C12 Cl2 Cl2 168.81(9) . 2_776 ?
C2 Cl1 Cl1 171.84(10) . 2_677 ?
C17 O3 Co2 124.88(15) . . ?
C9 O2 Co1 126.02(15) . . ?
C7 O1 Co1 125.40(15) . . ?
C19 O4 Co2 124.73(16) . . ?
C11 N2 Co2 119.87(14) . . ?
C11 N2 C15 117.91(18) . . ?
C15 N2 Co2 122.01(14) . . ?
C5 N1 Co1 122.20(14) . . ?
C1 N1 Co1 120.27(14) . . ?
C1 N1 C5 117.51(19) . . ?
O1 C7 C8 125.9(2) . . ?
O1 C7 C6 115.2(2) . . ?
C8 C7 C6 118.9(2) . . ?
O2 C9 C8 124.8(2) . . ?
O2 C9 C10 116.3(2) . . ?
C8 C9 C10 118.9(2) . . ?
O3 C17 C18 124.7(2) . . ?
O3 C17 C16 115.7(3) . . ?
C18 C17 C16 119.6(2) . . ?
N2 C11 H11 119.1 . . ?
N2 C11 C12 121.9(2) . . ?
C12 C11 H11 119.1 . . ?
O4 C19 C18 125.5(2) . . ?
O4 C19 C20 115.7(3) . . ?
C18 C19 C20 118.8(2) . . ?
N1 C5 H5 118.5 . . ?
N1 C5 C4 123.1(2) . . ?
C4 C5 H5 118.5 . . ?
N1 C1 H1 119.0 . . ?
N1 C1 C2 121.9(2) . . ?
C2 C1 H1 119.0 . . ?
C11 C12 Cl2 118.95(19) . . ?
C11 C12 C13 120.2(2) . . ?
C13 C12 Cl2 120.81(18) . . ?
N2 C15 H15 118.6 . . ?
N2 C15 C14 122.8(2) . . ?
C14 C15 H15 118.6 . . ?
C1 C2 Cl1 118.76(18) . . ?
C3 C2 Cl1 120.60(19) . . ?
C3 C2 C1 120.6(2) . . ?
C5 C4 H4 120.2 . . ?
C5 C4 C3 119.6(2) . . ?
C3 C4 H4 120.2 . . ?
C2 C3 C4 117.2(2) . . ?
C2 C3 H3 121.4 . . ?
C4 C3 H3 121.4 . . ?
C12 C13 H13 121.1 . . ?
C14 C13 C12 117.9(2) . . ?
C14 C13 H13 121.1 . . ?
C15 C14 H14 120.3 . . ?
C13 C14 C15 119.3(2) . . ?
C13 C14 H14 120.3 . . ?
C17 C18 C19 126.4(2) . . ?
C17 C18 H18 116.8 . . ?
C19 C18 H18 116.8 . . ?
C7 C8 C9 126.3(2) . . ?
C7 C8 H8 116.8 . . ?
C9 C8 H8 116.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
Co2 O3 C17 C18 -18.4(3) . . . . ?
Co2 O3 C17 C16 161.55(16) . . . . ?
Co2 O4 C19 C18 10.0(3) . . . . ?
Co2 O4 C19 C20 -170.73(17) . . . . ?
Co2 N2 C11 C12 172.73(16) . . . . ?
Co2 N2 C15 C14 -173.37(18) . . . . ?
Co1 O2 C9 C8 -4.3(3) . . . . ?
Co1 O2 C9 C10 176.26(15) . . . . ?
Co1 O1 C7 C8 11.0(3) . . . . ?
Co1 O1 C7 C6 -168.88(16) . . . . ?
Co1 N1 C5 C4 -178.15(19) . . . . ?
Co1 N1 C1 C2 178.46(18) . . . . ?
Cl2 Cl2 C12 C11 -42.9(6) 2_776 . . . ?
Cl2 Cl2 C12 C13 138.8(4) 2_776 . . . ?
Cl2 C12 C13 C14 178.27(19) . . . . ?
Cl1 C2 C3 C4 -179.3(2) . . . . ?
O3 C17 C18 C19 0.7(4) . . . . ?
O2 C9 C8 C7 -6.0(4) . . . . ?
O1 C7 C8 C9 2.3(4) . . . . ?
O4 C19 C18 C17 3.9(4) . . . . ?
N2 C11 C12 Cl2 -176.77(17) . . . . ?
N2 C11 C12 C13 1.5(4) . . . . ?
N2 C15 C14 C13 0.1(4) . . . . ?
N1 C5 C4 C3 0.0(4) . . . . ?
N1 C1 C2 Cl1 179.21(18) . . . . ?
N1 C1 C2 C3 -0.5(4) . . . . ?
C11 N2 C15 C14 1.4(3) . . . . ?
C11 C12 C13 C14 0.0(4) . . . . ?
C5 N1 C1 C2 0.3(3) . . . . ?
C5 C4 C3 C2 -0.2(4) . . . . ?
C1 N1 C5 C4 0.0(4) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C12 C13 C14 C15 -0.8(4) . . . . ?
C15 N2 C11 C12 -2.2(3) . . . . ?
C10 C9 C8 C7 173.4(2) . . . . ?
C6 C7 C8 C9 -177.8(2) . . . . ?
C16 C17 C18 C19 -179.3(2) . . . . ?
C20 C19 C18 C17 -175.3(2) . . . . ?

_olex2_date_sample_data_collection 2017-03-16
_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_2a
_database_code_depnum_ccdc_archive 'CCDC 1582550'
_audit_update_record             
;
2017-10-27 deposited with the CCDC.
2017-12-04 downloaded from the CCDC.
;
_audit_creation_date             2017-10-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H22 Br2 Co N2 O4'
_chemical_formula_sum            'C20 H22 Br2 Co N2 O4'
_chemical_formula_weight         573.14
_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'
Br Br -0.2901 2.4595 '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'
O O 0.0106 0.0060 '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                   6.4978(5)
_cell_length_b                   8.8500(7)
_cell_length_c                   10.3960(5)
_cell_angle_alpha                100.254(5)
_cell_angle_beta                 101.706(5)
_cell_angle_gamma                99.895(7)
_cell_volume                     562.47(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1382
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      29.1900
_cell_measurement_theta_min      4.7750
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.342
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66433
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark orange'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             285
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4189
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_min         4.268
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1820
_reflns_number_total             2194
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    ?
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.660
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         2194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.079
_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)+(0.0353P)²+0.2595P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0851
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C4(H4), C3(H3), C8(H8)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Br1 Br 0.50726(7) 0.21192(5) 0.96900(4) 0.07612(18) Uani 1 1 d . . . . .
Co1 Co 0.5000 0.5000 0.5000 0.04024(17) Uani 1 2 d S T P . .
O1 O 0.6665(3) 0.3292(3) 0.5150(2) 0.0485(5) Uani 1 1 d . . . . .
O2 O 0.2605(3) 0.3445(3) 0.3544(2) 0.0511(5) Uani 1 1 d . . . . .
N1 N 0.3477(4) 0.4368(3) 0.6629(2) 0.0456(6) Uani 1 1 d . . . . .
C2 C 0.3623(6) 0.3220(4) 0.8527(3) 0.0506(8) Uani 1 1 d . . . . .
C1 C 0.4422(5) 0.3579(4) 0.7475(3) 0.0484(7) Uani 1 1 d . . . . .
H1 H 0.5670 0.3262 0.7342 0.058 Uiso 1 1 calc R . . . .
C5 C 0.1691(5) 0.4794(4) 0.6837(3) 0.0512(8) Uani 1 1 d . . . . .
H5 H 0.1018 0.5344 0.6255 0.061 Uiso 1 1 calc R . . . .
C4 C 0.0788(6) 0.4466(5) 0.7861(4) 0.0629(9) Uani 1 1 d . . . . .
H4 H -0.0471 0.4785 0.7965 0.075 Uiso 1 1 calc R . . . .
C3 C 0.1760(6) 0.3663(4) 0.8732(4) 0.0613(9) Uani 1 1 d . . . . .
H3 H 0.1182 0.3424 0.9439 0.074 Uiso 1 1 calc R . . . .
C6 C 0.7946(7) 0.0998(5) 0.4599(4) 0.0721(11) Uani 1 1 d . . . . .
H6A H 0.9346 0.1609 0.4656 0.108 Uiso 1 1 calc GR . . . .
H6B H 0.7615 0.0087 0.3875 0.108 Uiso 1 1 calc GR . . . .
H6C H 0.7931 0.0672 0.5431 0.108 Uiso 1 1 calc GR . . . .
C7 C 0.6278(5) 0.1985(4) 0.4340(3) 0.0481(8) Uani 1 1 d . . . . .
C8 C 0.4484(6) 0.1396(4) 0.3276(4) 0.0589(9) Uani 1 1 d . . . . .
H8 H 0.4428 0.0434 0.2722 0.071 Uiso 1 1 calc R . . . .
C9 C 0.2751(5) 0.2115(4) 0.2959(3) 0.0507(8) Uani 1 1 d . . . . .
C10 C 0.0854(7) 0.1211(5) 0.1821(4) 0.0782(12) Uani 1 1 d . . . . .
H10A H 0.0308 0.0214 0.2006 0.117 Uiso 1 1 calc GR . . . .
H10B H 0.1308 0.1044 0.0993 0.117 Uiso 1 1 calc GR . . . .
H10C H -0.0256 0.1803 0.1742 0.117 Uiso 1 1 calc GR . . . .


_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
Br1 C2 1.890(3) . ?
Co1 O1 2.0143(19) . ?
Co1 O1 2.0143(19) 2_666 ?
Co1 O2 2.043(2) . ?
Co1 O2 2.043(2) 2_666 ?
Co1 N1 2.233(2) . ?
Co1 N1 2.233(2) 2_666 ?
O1 C7 1.256(4) . ?
O2 C9 1.254(4) . ?
N1 C1 1.336(4) . ?
N1 C5 1.326(4) . ?
C2 C1 1.365(4) . ?
C2 C3 1.380(5) . ?
C1 H1 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.366(5) . ?
C4 H4 0.9300 . ?
C4 C3 1.370(5) . ?
C3 H3 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C6 C7 1.517(4) . ?
C7 C8 1.384(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.397(5) . ?
C9 C10 1.514(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 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
O1 Co1 O1 180.0 2_666 . ?
O1 Co1 O2 90.33(9) . 2_666 ?
O1 Co1 O2 89.67(9) . . ?
O1 Co1 O2 89.67(9) 2_666 2_666 ?
O1 Co1 O2 90.33(9) 2_666 . ?
O1 Co1 N1 89.78(9) . . ?
O1 Co1 N1 90.22(9) . 2_666 ?
O1 Co1 N1 89.78(9) 2_666 2_666 ?
O1 Co1 N1 90.22(9) 2_666 . ?
O2 Co1 O2 180.0 2_666 . ?
O2 Co1 N1 91.79(9) . . ?
O2 Co1 N1 88.21(9) 2_666 . ?
O2 Co1 N1 88.21(9) . 2_666 ?
O2 Co1 N1 91.79(9) 2_666 2_666 ?
N1 Co1 N1 180.0 . 2_666 ?
C7 O1 Co1 126.2(2) . . ?
C9 O2 Co1 125.0(2) . . ?
C1 N1 Co1 119.7(2) . . ?
C5 N1 Co1 122.8(2) . . ?
C5 N1 C1 117.5(3) . . ?
C1 C2 Br1 119.8(2) . . ?
C1 C2 C3 119.7(3) . . ?
C3 C2 Br1 120.4(2) . . ?
N1 C1 C2 122.4(3) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
N1 C5 H5 118.3 . . ?
N1 C5 C4 123.4(3) . . ?
C4 C5 H5 118.3 . . ?
C5 C4 H4 120.4 . . ?
C5 C4 C3 119.2(3) . . ?
C3 C4 H4 120.4 . . ?
C2 C3 H3 121.1 . . ?
C4 C3 C2 117.8(3) . . ?
C4 C3 H3 121.1 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
O1 C7 C6 115.2(3) . . ?
O1 C7 C8 125.6(3) . . ?
C8 C7 C6 119.2(3) . . ?
C7 C8 H8 117.0 . . ?
C7 C8 C9 126.0(3) . . ?
C9 C8 H8 117.0 . . ?
O2 C9 C8 125.9(3) . . ?
O2 C9 C10 116.4(3) . . ?
C8 C9 C10 117.7(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C5 H5 O2 0.93 2.78 3.412(4) 126.3 2_566
C4 H4 O2 0.93 2.75 3.386(4) 126.2 2_566

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
Br1 C2 C1 N1 -179.3(2) . . . . ?
Br1 C2 C3 C4 179.6(3) . . . . ?
Co1 O1 C7 C6 172.8(2) . . . . ?
Co1 O1 C7 C8 -8.0(4) . . . . ?
Co1 O2 C9 C8 6.3(4) . . . . ?
Co1 O2 C9 C10 -174.6(2) . . . . ?
Co1 N1 C1 C2 177.0(2) . . . . ?
Co1 N1 C5 C4 -177.4(3) . . . . ?
O1 C7 C8 C9 -3.3(6) . . . . ?
N1 C5 C4 C3 0.3(6) . . . . ?
C1 N1 C5 C4 0.0(5) . . . . ?
C1 C2 C3 C4 -0.5(5) . . . . ?
C5 N1 C1 C2 -0.5(5) . . . . ?
C5 C4 C3 C2 0.0(6) . . . . ?
C3 C2 C1 N1 0.8(5) . . . . ?
C6 C7 C8 C9 175.8(3) . . . . ?
C7 C8 C9 O2 4.2(6) . . . . ?
C7 C8 C9 C10 -175.0(3) . . . . ?

_olex2_date_sample_data_collection 2017-03-16
_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_4a
_database_code_depnum_ccdc_archive 'CCDC 1582548'
_audit_update_record             
;
2017-10-27 deposited with the CCDC.
2017-12-04 downloaded from the CCDC.
;
_audit_creation_date             2017-10-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H20 Cl2 Co N4 O4'
_chemical_formula_sum            'C18 H20 Cl2 Co N4 O4'
_chemical_formula_weight         486.21
_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'
O O 0.0106 0.0060 '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                   6.3162(4)
_cell_length_b                   8.8584(8)
_cell_length_c                   10.1891(5)
_cell_angle_alpha                99.706(6)
_cell_angle_beta                 101.645(5)
_cell_angle_gamma                100.278(7)
_cell_volume                     536.88(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1642
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      30.2330
_cell_measurement_theta_min      4.5390
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             249
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4382
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.994
_diffrn_reflns_theta_min         4.353
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2288
_reflns_number_total             2587
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    ?
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         2587
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      1.075
_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)+(0.0483P)²+0.0469P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0977
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C7(H7), C3(H3)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.5000 0.5000 0.5000 0.04031(13) Uani 1 2 d S T P . .
Cl1 Cl 0.49869(13) 0.21582(9) 0.96726(7) 0.0814(2) Uani 1 1 d . . . . .
O1 O 0.3321(2) 0.67167(17) 0.48575(14) 0.0493(3) Uani 1 1 d . . . . .
O2 O 0.7464(2) 0.65105(17) 0.64800(13) 0.0505(3) Uani 1 1 d . . . . .
N1 N 0.3459(2) 0.4357(2) 0.66890(15) 0.0456(4) Uani 1 1 d . . . . .
N2 N 0.1922(3) 0.3699(3) 0.8954(2) 0.0664(5) Uani 1 1 d . . . . .
C1 C 0.4445(3) 0.3549(3) 0.7520(2) 0.0498(5) Uani 1 1 d . . . . .
H1 H 0.5686 0.3197 0.7351 0.060 Uiso 1 1 calc R . . . .
C6 C 0.3734(4) 0.8019(2) 0.5704(2) 0.0487(5) Uani 1 1 d . . . . .
C8 C 0.7326(3) 0.7828(3) 0.71213(19) 0.0510(5) Uani 1 1 d . . . . .
C2 C 0.3653(4) 0.3228(3) 0.8625(2) 0.0529(5) Uani 1 1 d . . . . .
C4 C 0.1695(3) 0.4828(3) 0.6985(2) 0.0537(5) Uani 1 1 d . . . . .
H4 H 0.0944 0.5382 0.6421 0.064 Uiso 1 1 calc R . . . .
C7 C 0.5562(4) 0.8549(3) 0.6808(2) 0.0585(5) Uani 1 1 d . . . . .
H7 H 0.5612 0.9484 0.7400 0.070 Uiso 1 1 calc R . . . .
C5 C 0.2052(5) 0.9008(3) 0.5434(3) 0.0715(7) Uani 1 1 d . . . . .
H5A H 0.1999 0.9267 0.4552 0.107 Uiso 1 1 calc GR . . . .
H5B H 0.2466 0.9956 0.6130 0.107 Uiso 1 1 calc GR . . . .
H5C H 0.0620 0.8433 0.5448 0.107 Uiso 1 1 calc GR . . . .
C3 C 0.0958(4) 0.4508(3) 0.8113(3) 0.0674(6) Uani 1 1 d . . . . .
H3 H -0.0266 0.4874 0.8295 0.081 Uiso 1 1 calc R . . . .
C9 C 0.9272(4) 0.8640(4) 0.8310(2) 0.0794(8) Uani 1 1 d . . . . .
H9A H 0.9197 0.8146 0.9073 0.119 Uiso 1 1 calc GR . . . .
H9B H 0.9228 0.9725 0.8570 0.119 Uiso 1 1 calc GR . . . .
H9C H 1.0628 0.8566 0.8041 0.119 Uiso 1 1 calc GR . . . .


_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 O1 2.0113(12) . ?
Co1 O1 2.0113(12) 2_666 ?
Co1 O2 2.0288(13) 2_666 ?
Co1 O2 2.0288(14) . ?
Co1 N1 2.2456(16) . ?
Co1 N1 2.2456(16) 2_666 ?
Cl1 C2 1.735(2) . ?
O1 C6 1.268(2) . ?
O2 C8 1.265(2) . ?
N1 C1 1.330(2) . ?
N1 C4 1.329(2) . ?
N2 C2 1.321(3) . ?
N2 C3 1.331(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.372(3) . ?
C6 C7 1.387(3) . ?
C6 C5 1.506(3) . ?
C8 C7 1.389(3) . ?
C8 C9 1.512(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.376(3) . ?
C7 H7 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C3 H3 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 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
O1 Co1 O1 180.0 . 2_666 ?
O1 Co1 O2 90.15(6) 2_666 . ?
O1 Co1 O2 89.85(6) 2_666 2_666 ?
O1 Co1 O2 89.85(6) . . ?
O1 Co1 O2 90.15(6) . 2_666 ?
O1 Co1 N1 89.45(6) 2_666 . ?
O1 Co1 N1 90.55(6) 2_666 2_666 ?
O1 Co1 N1 89.45(6) . 2_666 ?
O1 Co1 N1 90.55(6) . . ?
O2 Co1 O2 180.0 . 2_666 ?
O2 Co1 N1 92.78(6) 2_666 . ?
O2 Co1 N1 87.22(6) . . ?
O2 Co1 N1 87.22(6) 2_666 2_666 ?
O2 Co1 N1 92.78(6) . 2_666 ?
N1 Co1 N1 180.0 . 2_666 ?
C6 O1 Co1 126.00(13) . . ?
C8 O2 Co1 125.36(13) . . ?
C1 N1 Co1 118.76(13) . . ?
C4 N1 Co1 124.27(14) . . ?
C4 N1 C1 116.78(17) . . ?
C2 N2 C3 114.72(19) . . ?
N1 C1 H1 119.6 . . ?
N1 C1 C2 120.77(19) . . ?
C2 C1 H1 119.6 . . ?
O1 C6 C7 124.90(18) . . ?
O1 C6 C5 114.8(2) . . ?
C7 C6 C5 120.3(2) . . ?
O2 C8 C7 125.11(19) . . ?
O2 C8 C9 115.4(2) . . ?
C7 C8 C9 119.5(2) . . ?
N2 C2 Cl1 117.27(17) . . ?
N2 C2 C1 123.7(2) . . ?
C1 C2 Cl1 119.03(17) . . ?
N1 C4 H4 119.4 . . ?
N1 C4 C3 121.1(2) . . ?
C3 C4 H4 119.4 . . ?
C6 C7 C8 126.71(19) . . ?
C6 C7 H7 116.6 . . ?
C8 C7 H7 116.6 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C6 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C3 C4 122.9(2) . . ?
N2 C3 H3 118.6 . . ?
C4 C3 H3 118.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4 O2 0.93 2.58 3.279(2) 132.4 1_455
C3 H3 O2 0.93 2.86 3.420(3) 120.3 1_455

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 O1 C6 C7 6.9(3) . . . . ?
Co1 O1 C6 C5 -173.15(13) . . . . ?
Co1 O2 C8 C7 -8.3(3) . . . . ?
Co1 O2 C8 C9 171.93(15) . . . . ?
Co1 N1 C1 C2 175.28(16) . . . . ?
Co1 N1 C4 C3 -174.01(19) . . . . ?
O1 C6 C7 C8 5.4(4) . . . . ?
O2 C8 C7 C6 -4.5(4) . . . . ?
N1 C1 C2 Cl1 179.57(16) . . . . ?
N1 C1 C2 N2 -1.0(4) . . . . ?
N1 C4 C3 N2 -1.1(4) . . . . ?
C1 N1 C4 C3 1.0(3) . . . . ?
C2 N2 C3 C4 0.2(4) . . . . ?
C4 N1 C1 C2 0.0(3) . . . . ?
C5 C6 C7 C8 -174.6(2) . . . . ?
C3 N2 C2 Cl1 -179.7(2) . . . . ?
C3 N2 C2 C1 0.8(4) . . . . ?
C9 C8 C7 C6 175.3(2) . . . . ?

_olex2_date_sample_data_collection 2016-03-18
_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_5b
_database_code_depnum_ccdc_archive 'CCDC 1582541'
_audit_update_record             
;
2017-10-27 deposited with the CCDC.
2017-12-04 downloaded from the CCDC.
;
_audit_creation_date             2017-10-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H20 Br2 N4 Ni O4'
_chemical_formula_sum            'C18 H20 Br2 N4 Ni O4'
_chemical_formula_weight         574.91
_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'
Br Br -0.2901 2.4595 '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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.3344(4)
_cell_length_b                   9.0280(8)
_cell_length_c                   10.1145(7)
_cell_angle_alpha                101.295(7)
_cell_angle_beta                 100.541(6)
_cell_angle_gamma                99.102(7)
_cell_volume                     546.23(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1433
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      31.2180
_cell_measurement_theta_min      4.3170
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.576
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48123
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light blue'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.748
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             286
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4386
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_min         4.141
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1970
_reflns_number_total             2375
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    ?
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.622
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.056
_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     135
_refine_ls_number_reflns         2375
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0312
_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)+(0.0244P)²+0.2513P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0632
_refine_ls_wR_factor_ref         0.0675
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C7(H7), C3(H3)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Ni1 Ni 0.5000 0.5000 0.5000 0.03640(12) Uani 1 2 d S T P . .
Br1 Br 0.49103(6) 0.78399(4) 0.02841(3) 0.07050(14) Uani 1 1 d . . . . .
O1 O 0.6735(3) 0.3337(2) 0.51120(18) 0.0450(4) Uani 1 1 d . . . . .
O2 O 0.2586(3) 0.3560(2) 0.35168(18) 0.0466(4) Uani 1 1 d . . . . .
N1 N 0.6512(3) 0.5624(2) 0.3371(2) 0.0409(5) Uani 1 1 d . . . . .
N2 N 0.8151(4) 0.6289(3) 0.1132(3) 0.0597(6) Uani 1 1 d . . . . .
C6 C 0.6252(5) 0.2016(3) 0.4299(3) 0.0456(6) Uani 1 1 d . . . . .
C1 C 0.5533(4) 0.6406(3) 0.2537(3) 0.0445(6) Uani 1 1 d . . . . .
H1 H 0.4266 0.6739 0.2698 0.053 Uiso 1 1 calc R . . . .
C4 C 0.8321(4) 0.5182(3) 0.3082(3) 0.0493(7) Uani 1 1 d . . . . .
H4 H 0.9062 0.4640 0.3643 0.059 Uiso 1 1 calc R . . . .
C2 C 0.6377(4) 0.6727(3) 0.1440(3) 0.0458(6) Uani 1 1 d . . . . .
C8 C 0.2686(4) 0.2219(3) 0.2908(3) 0.0468(6) Uani 1 1 d . . . . .
C7 C 0.4406(5) 0.1464(3) 0.3239(3) 0.0542(7) Uani 1 1 d . . . . .
H7 H 0.4298 0.0488 0.2689 0.065 Uiso 1 1 calc R . . . .
C3 C 0.9113(5) 0.5510(4) 0.1972(3) 0.0609(8) Uani 1 1 d . . . . .
H3 H 1.0372 0.5173 0.1801 0.073 Uiso 1 1 calc R . . . .
C5 C 0.7895(5) 0.0993(4) 0.4568(4) 0.0677(9) Uani 1 1 d . . . . .
H5A H 0.9340 0.1540 0.4602 0.102 Uiso 1 1 calc GR . . . .
H5B H 0.7527 0.0076 0.3838 0.102 Uiso 1 1 calc GR . . . .
H5C H 0.7855 0.0717 0.5434 0.102 Uiso 1 1 calc GR . . . .
C9 C 0.0756(5) 0.1408(4) 0.1741(3) 0.0735(10) Uani 1 1 d . . . . .
H9A H -0.0580 0.1539 0.2026 0.110 Uiso 1 1 calc GR . . . .
H9B H 0.0781 0.0330 0.1501 0.110 Uiso 1 1 calc GR . . . .
H9C H 0.0838 0.1840 0.0952 0.110 Uiso 1 1 calc GR . . . .


_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
Ni1 O1 2.0046(16) 2_666 ?
Ni1 O1 2.0046(16) . ?
Ni1 O2 2.0116(17) 2_666 ?
Ni1 O2 2.0116(17) . ?
Ni1 N1 2.172(2) 2_666 ?
Ni1 N1 2.172(2) . ?
Br1 C2 1.896(3) . ?
O1 C6 1.266(3) . ?
O2 C8 1.263(3) . ?
N1 C1 1.333(3) . ?
N1 C4 1.334(3) . ?
N2 C2 1.318(3) . ?
N2 C3 1.330(4) . ?
C6 C7 1.383(4) . ?
C6 C5 1.519(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.377(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.375(4) . ?
C8 C7 1.399(4) . ?
C8 C9 1.508(4) . ?
C7 H7 0.9300 . ?
C3 H3 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 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
O1 Ni1 O1 180.00(11) 2_666 . ?
O1 Ni1 O2 91.64(7) . . ?
O1 Ni1 O2 88.36(7) . 2_666 ?
O1 Ni1 O2 88.36(7) 2_666 . ?
O1 Ni1 O2 91.64(7) 2_666 2_666 ?
O1 Ni1 N1 89.53(7) . 2_666 ?
O1 Ni1 N1 90.47(7) . . ?
O1 Ni1 N1 89.53(7) 2_666 . ?
O1 Ni1 N1 90.47(7) 2_666 2_666 ?
O2 Ni1 O2 180.0 . 2_666 ?
O2 Ni1 N1 87.97(7) 2_666 2_666 ?
O2 Ni1 N1 92.03(7) . 2_666 ?
O2 Ni1 N1 92.03(7) 2_666 . ?
O2 Ni1 N1 87.97(7) . . ?
N1 Ni1 N1 180.0 2_666 . ?
C6 O1 Ni1 124.93(17) . . ?
C8 O2 Ni1 124.90(17) . . ?
C1 N1 Ni1 119.45(16) . . ?
C1 N1 C4 116.6(2) . . ?
C4 N1 Ni1 123.80(17) . . ?
C2 N2 C3 115.1(2) . . ?
O1 C6 C7 125.8(2) . . ?
O1 C6 C5 114.5(3) . . ?
C7 C6 C5 119.7(3) . . ?
N1 C1 H1 119.7 . . ?
N1 C1 C2 120.7(2) . . ?
C2 C1 H1 119.7 . . ?
N1 C4 H4 119.3 . . ?
N1 C4 C3 121.3(3) . . ?
C3 C4 H4 119.3 . . ?
N2 C2 Br1 117.6(2) . . ?
N2 C2 C1 123.6(2) . . ?
C1 C2 Br1 118.8(2) . . ?
O2 C8 C7 125.3(3) . . ?
O2 C8 C9 115.4(3) . . ?
C7 C8 C9 119.3(3) . . ?
C6 C7 C8 126.8(3) . . ?
C6 C7 H7 116.6 . . ?
C8 C7 H7 116.6 . . ?
N2 C3 C4 122.7(3) . . ?
N2 C3 H3 118.7 . . ?
C4 C3 H3 118.7 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C6 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4 O2 0.93 2.59 3.272(3) 130.8 1_655
C3 H3 O2 0.93 2.80 3.380(3) 121.4 1_655

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
Ni1 O1 C6 C7 -3.2(4) . . . . ?
Ni1 O1 C6 C5 177.35(17) . . . . ?
Ni1 O2 C8 C7 5.6(4) . . . . ?
Ni1 O2 C8 C9 -174.61(19) . . . . ?
Ni1 N1 C1 C2 -175.6(2) . . . . ?
Ni1 N1 C4 C3 174.9(2) . . . . ?
O1 C6 C7 C8 -3.4(4) . . . . ?
O2 C8 C7 C6 2.0(4) . . . . ?
N1 C1 C2 Br1 179.87(19) . . . . ?
N1 C1 C2 N2 0.6(4) . . . . ?
N1 C4 C3 N2 0.5(5) . . . . ?
C1 N1 C4 C3 -0.5(4) . . . . ?
C4 N1 C1 C2 0.0(4) . . . . ?
C2 N2 C3 C4 0.0(5) . . . . ?
C3 N2 C2 Br1 -179.8(2) . . . . ?
C3 N2 C2 C1 -0.5(4) . . . . ?
C5 C6 C7 C8 176.1(3) . . . . ?
C9 C8 C7 C6 -177.8(3) . . . . ?

_olex2_date_sample_data_collection 2016-02-13
_olex2_submission_special_instructions 'No special instructions were received'
