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

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

data_AZ164
_database_code_depnum_ccdc_archive 'CCDC 1580804'
_audit_update_record             
;
2017-10-19 deposited with the CCDC.
2018-03-27 downloaded from the CCDC.
;
_audit_creation_date             2017-09-07
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            '[Ni(II)(propargyl-cyclam)](2Cl)'
_chemical_name_systematic        Ni(propargyl-cyclam)
_chemical_formula_moiety         'C13 H26 Cl2 N4 Ni'
_chemical_formula_sum            'C13 H26 Cl2 N4 Ni'
_chemical_formula_weight         367.99
_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 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 '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                   6.5736(4)
_cell_length_b                   14.4609(7)
_cell_length_c                   17.5037(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.312(4)
_cell_angle_gamma                90
_cell_volume                     1663.47(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9232
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      68.245
_cell_measurement_theta_min      3.966
_shelx_estimated_absorpt_T_max   0.834
_shelx_estimated_absorpt_T_min   0.435
_exptl_absorpt_coefficient_mu    4.597
_exptl_absorpt_correction_T_max  0.3201
_exptl_absorpt_correction_T_min  0.2167
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0940 before and 0.0655 after correction. The Ratio of minimum to maximum transmission is 0.6770. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'Light Purple'
_exptl_crystal_colour_modifier   Light
_exptl_crystal_colour_primary    Purple
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             776
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.217
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_min          0.041
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25028
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         68.479
_diffrn_reflns_theta_min         3.965
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker Microstar FR-592'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2707
_reflns_number_total             3026
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.600
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3026
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0517
_refine_ls_restrained_S_all      1.137
_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)+(0.0360P)²+4.6399P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1242
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 N2(H2), N3(H3), N4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.c :
 C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.52387(9) 0.71472(4) 0.34507(3) 0.02500(19) Uani 1 1 d . . . . .
Cl1 Cl 0.24291(13) 0.60471(6) 0.36032(5) 0.0312(2) Uani 1 1 d . . . . .
Cl2 Cl 0.82006(14) 0.83101(7) 0.34249(6) 0.0329(2) Uani 1 1 d . . . . .
N1 N 0.5169(5) 0.7034(2) 0.22261(18) 0.0306(7) Uani 1 1 d . . . . .
N2 N 0.3206(5) 0.8221(2) 0.3498(2) 0.0325(7) Uani 1 1 d . . . . .
H2 H 0.181407 0.794539 0.344992 0.039 Uiso 1 1 calc R . . . .
N3 N 0.5466(5) 0.7285(3) 0.46319(18) 0.0344(8) Uani 1 1 d . . . . .
H3 H 0.669697 0.767366 0.474083 0.041 Uiso 1 1 calc R . . . .
N4 N 0.7438(5) 0.6154(2) 0.34347(18) 0.0272(7) Uani 1 1 d . . . . .
H4 H 0.876348 0.648456 0.350954 0.033 Uiso 1 1 calc R . . . .
C1 C 0.5085(7) 0.7970(3) 0.1867(2) 0.0367(10) Uani 1 1 d . . . . .
H1A H 0.503261 0.789667 0.130455 0.044 Uiso 1 1 calc R . . . .
H1B H 0.635099 0.830732 0.200431 0.044 Uiso 1 1 calc R . . . .
C2 C 0.3267(7) 0.8548(3) 0.2106(3) 0.0422(11) Uani 1 1 d . . . . .
H2A H 0.311890 0.907190 0.174520 0.051 Uiso 1 1 calc R . . . .
H2B H 0.202880 0.816254 0.204890 0.051 Uiso 1 1 calc R . . . .
C3 C 0.3336(6) 0.8935(3) 0.2909(3) 0.0392(10) Uani 1 1 d . . . . .
H3A H 0.462028 0.928397 0.298709 0.047 Uiso 1 1 calc R . . . .
H3B H 0.219467 0.937464 0.296581 0.047 Uiso 1 1 calc R . . . .
C4 C 0.3406(7) 0.8613(3) 0.4281(3) 0.0428(11) Uani 1 1 d . . . . .
H4A H 0.216608 0.896816 0.440088 0.051 Uiso 1 1 calc R . . . .
H4B H 0.458342 0.903909 0.431039 0.051 Uiso 1 1 calc R . . . .
C5 C 0.3703(7) 0.7838(3) 0.4856(3) 0.0425(11) Uani 1 1 d . . . . .
H5A H 0.394101 0.809853 0.537382 0.051 Uiso 1 1 calc R . . . .
H5B H 0.247071 0.744529 0.486566 0.051 Uiso 1 1 calc R . . . .
C6 C 0.5738(7) 0.6437(3) 0.5073(2) 0.0414(10) Uani 1 1 d . . . . .
H6A H 0.449493 0.605408 0.501668 0.050 Uiso 1 1 calc R . . . .
H6B H 0.591369 0.659708 0.562085 0.050 Uiso 1 1 calc R . . . .
C7 C 0.7558(7) 0.5875(3) 0.4826(2) 0.0408(10) Uani 1 1 d . . . . .
H7A H 0.779480 0.537448 0.520384 0.049 Uiso 1 1 calc R . . . .
H7B H 0.877086 0.628051 0.484261 0.049 Uiso 1 1 calc R . . . .
C8 C 0.7383(6) 0.5441(3) 0.4034(2) 0.0355(9) Uani 1 1 d . . . . .
H8A H 0.851921 0.500147 0.396594 0.043 Uiso 1 1 calc R . . . .
H8B H 0.609177 0.509143 0.398681 0.043 Uiso 1 1 calc R . . . .
C9 C 0.7453(6) 0.5767(3) 0.2650(2) 0.0364(9) Uani 1 1 d . . . . .
H9A H 0.635927 0.530158 0.258482 0.044 Uiso 1 1 calc R . . . .
H9B H 0.877379 0.546214 0.255834 0.044 Uiso 1 1 calc R . . . .
C10 C 0.7120(6) 0.6561(3) 0.2083(2) 0.0363(9) Uani 1 1 d . . . . .
H10A H 0.825261 0.700912 0.213589 0.044 Uiso 1 1 calc R . . . .
H10B H 0.710800 0.631573 0.155527 0.044 Uiso 1 1 calc R . . . .
C11 C 0.3457(7) 0.6455(3) 0.1909(2) 0.0391(10) Uani 1 1 d . . . . .
H11A H 0.347508 0.584985 0.217321 0.047 Uiso 1 1 calc R . . . .
H11B H 0.215373 0.676235 0.202461 0.047 Uiso 1 1 calc R . . . .
C12 C 0.3530(7) 0.6293(3) 0.1074(3) 0.0414(10) Uani 1 1 d . . . . .
C13 C 0.3617(8) 0.6117(3) 0.0418(3) 0.0473(11) Uani 1 1 d . . . . .
H13 H 0.368686 0.597522 -0.011047 0.057 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 Cl1 2.4568(11) . ?
Ni1 Cl2 2.5738(11) . ?
Ni1 N1 2.149(3) . ?
Ni1 N2 2.051(3) . ?
Ni1 N3 2.079(3) . ?
Ni1 N4 2.039(3) . ?
N1 C1 1.493(5) . ?
N1 C10 1.480(5) . ?
N1 C11 1.498(5) . ?
N2 H2 1.0000 . ?
N2 C3 1.464(5) . ?
N2 C4 1.487(6) . ?
N3 H3 1.0000 . ?
N3 C5 1.469(6) . ?
N3 C6 1.459(6) . ?
N4 H4 1.0000 . ?
N4 C8 1.472(5) . ?
N4 C9 1.483(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.525(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.511(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.515(7) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.517(7) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.524(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.529(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.482(6) . ?
C12 C13 1.179(7) . ?
C13 H13 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Ni1 Cl2 174.77(4) . . ?
N1 Ni1 Cl1 93.44(9) . . ?
N1 Ni1 Cl2 91.79(9) . . ?
N2 Ni1 Cl1 89.65(10) . . ?
N2 Ni1 Cl2 89.99(10) . . ?
N2 Ni1 N1 95.67(13) . . ?
N2 Ni1 N3 85.38(14) . . ?
N3 Ni1 Cl1 89.49(10) . . ?
N3 Ni1 Cl2 85.28(10) . . ?
N3 Ni1 N1 176.89(14) . . ?
N4 Ni1 Cl1 94.60(9) . . ?
N4 Ni1 Cl2 85.60(9) . . ?
N4 Ni1 N1 86.07(13) . . ?
N4 Ni1 N2 175.31(13) . . ?
N4 Ni1 N3 92.66(14) . . ?
C1 N1 Ni1 110.5(3) . . ?
C1 N1 C11 109.3(3) . . ?
C10 N1 Ni1 101.8(2) . . ?
C10 N1 C1 111.8(3) . . ?
C10 N1 C11 109.0(3) . . ?
C11 N1 Ni1 114.2(2) . . ?
Ni1 N2 H2 106.9 . . ?
C3 N2 Ni1 117.2(3) . . ?
C3 N2 H2 106.9 . . ?
C3 N2 C4 112.1(3) . . ?
C4 N2 Ni1 106.4(3) . . ?
C4 N2 H2 106.9 . . ?
Ni1 N3 H3 106.4 . . ?
C5 N3 Ni1 106.2(3) . . ?
C5 N3 H3 106.4 . . ?
C6 N3 Ni1 116.8(3) . . ?
C6 N3 H3 106.4 . . ?
C6 N3 C5 113.8(3) . . ?
Ni1 N4 H4 106.1 . . ?
C8 N4 Ni1 117.0(2) . . ?
C8 N4 H4 106.1 . . ?
C8 N4 C9 113.4(3) . . ?
C9 N4 Ni1 107.3(2) . . ?
C9 N4 H4 106.1 . . ?
N1 C1 H1A 108.8 . . ?
N1 C1 H1B 108.8 . . ?
N1 C1 C2 113.8(3) . . ?
H1A C1 H1B 107.7 . . ?
C2 C1 H1A 108.8 . . ?
C2 C1 H1B 108.8 . . ?
C1 C2 H2A 108.1 . . ?
C1 C2 H2B 108.1 . . ?
H2A C2 H2B 107.3 . . ?
C3 C2 C1 116.8(4) . . ?
C3 C2 H2A 108.1 . . ?
C3 C2 H2B 108.1 . . ?
N2 C3 C2 113.1(3) . . ?
N2 C3 H3A 109.0 . . ?
N2 C3 H3B 109.0 . . ?
C2 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
N2 C4 H4A 109.7 . . ?
N2 C4 H4B 109.7 . . ?
N2 C4 C5 109.8(4) . . ?
H4A C4 H4B 108.2 . . ?
C5 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
N3 C5 C4 108.4(3) . . ?
N3 C5 H5A 110.0 . . ?
N3 C5 H5B 110.0 . . ?
C4 C5 H5A 110.0 . . ?
C4 C5 H5B 110.0 . . ?
H5A C5 H5B 108.4 . . ?
N3 C6 H6A 109.0 . . ?
N3 C6 H6B 109.0 . . ?
N3 C6 C7 112.8(3) . . ?
H6A C6 H6B 107.8 . . ?
C7 C6 H6A 109.0 . . ?
C7 C6 H6B 109.0 . . ?
C6 C7 H7A 108.3 . . ?
C6 C7 H7B 108.3 . . ?
C6 C7 C8 115.9(3) . . ?
H7A C7 H7B 107.4 . . ?
C8 C7 H7A 108.3 . . ?
C8 C7 H7B 108.3 . . ?
N4 C8 C7 111.0(3) . . ?
N4 C8 H8A 109.4 . . ?
N4 C8 H8B 109.4 . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
N4 C9 H9A 110.0 . . ?
N4 C9 H9B 110.0 . . ?
N4 C9 C10 108.3(3) . . ?
H9A C9 H9B 108.4 . . ?
C10 C9 H9A 110.0 . . ?
C10 C9 H9B 110.0 . . ?
N1 C10 C9 110.5(3) . . ?
N1 C10 H10A 109.6 . . ?
N1 C10 H10B 109.6 . . ?
C9 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
N1 C11 H11A 108.7 . . ?
N1 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C12 C11 N1 114.4(4) . . ?
C12 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
C13 C12 C11 176.5(5) . . ?
C12 C13 H13 180.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 Cl2 1.00 2.43 3.293(3) 143.8 1_455 yes
N4 H4 Cl1 1.00 2.49 3.291(3) 136.5 1_655 yes

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_az188
_database_code_depnum_ccdc_archive 'CCDC 1580806'
_audit_update_record             
;
2017-10-19 deposited with the CCDC.
2018-03-27 downloaded from the CCDC.
;
_audit_creation_date             2017-08-25
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            '[Ni(II)(hexynyl-cyclam)]2+'
_chemical_name_systematic        Ni(hexynyl-cyclam)
_chemical_formula_moiety         'C16 H34 Cl N4 Ni O, Cl'
_chemical_formula_sum            'C16 H34 Cl2 N4 Ni O'
_chemical_formula_weight         428.08
_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                   8.5522(3)
_cell_length_b                   9.3730(3)
_cell_length_c                   13.4983(4)
_cell_angle_alpha                109.220(2)
_cell_angle_beta                 99.489(2)
_cell_angle_gamma                91.607(2)
_cell_volume                     1003.79(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4548
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.31
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.886
_exptl_absorpt_coefficient_mu    1.244
_exptl_absorpt_correction_T_max  0.4908
_exptl_absorpt_correction_T_min  0.4457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0604 before and 0.0468 after correction. The Ratio of minimum to maximum transmission is 0.9081. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16660
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.682
_diffrn_reflns_theta_min         2.310
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Bruker APEX CCD'
_diffrn_detector_area_resol_mean 8.0
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2930
_reflns_number_total             3812
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_refine_diff_density_max         0.583
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3812
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.026
_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)+(0.0447P)²+0.3151P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0924
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O1-H1A = O1-H1B
 0.84 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 N2(H2), N3(H3), N4(H4)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B),
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B),
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
3.c :
 C1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.43848(4) 0.68977(4) 0.78460(3) 0.01231(12) Uani 1 1 d . . . . .
Cl1 Cl 0.33968(9) 0.80839(8) 0.95673(6) 0.01887(19) Uani 1 1 d . . . . .
O1 O 0.5490(3) 0.5688(2) 0.65130(17) 0.0177(5) Uani 1 1 d D . . . .
H1A H 0.492(4) 0.495(3) 0.608(2) 0.027 Uiso 1 1 d DR . . . .
H1B H 0.596(4) 0.602(4) 0.614(2) 0.027 Uiso 1 1 d DR . . . .
N1 N 0.2843(3) 0.7997(3) 0.69710(18) 0.0139(5) Uani 1 1 d . . . . .
N2 N 0.2844(3) 0.4981(3) 0.74834(19) 0.0167(6) Uani 1 1 d . . . . .
H2 H 0.291255 0.430734 0.674632 0.020 Uiso 1 1 calc R . . . .
N3 N 0.5907(3) 0.5879(3) 0.87341(19) 0.0162(6) Uani 1 1 d . . . . .
H3 H 0.575415 0.633751 0.948950 0.019 Uiso 1 1 calc R . . . .
N4 N 0.5915(3) 0.8813(3) 0.82941(19) 0.0153(6) Uani 1 1 d . . . . .
H4 H 0.580647 0.940726 0.904118 0.018 Uiso 1 1 calc R . . . .
C1 C 0.0968(4) 0.7546(4) 0.1332(3) 0.0285(8) Uani 1 1 d . . . . .
H1 H 0.101841 0.713706 0.059524 0.034 Uiso 1 1 calc R . . . .
C2 C 0.0906(4) 0.8062(3) 0.2260(3) 0.0216(7) Uani 1 1 d . . . . .
C3 C 0.0919(4) 0.8623(4) 0.3396(3) 0.0243(8) Uani 1 1 d . . . . .
H3A H -0.016739 0.844374 0.351930 0.029 Uiso 1 1 calc R . . . .
H3B H 0.120256 0.973273 0.366897 0.029 Uiso 1 1 calc R . . . .
C4 C 0.2089(4) 0.7883(4) 0.4036(2) 0.0223(7) Uani 1 1 d . . . . .
H4A H 0.198614 0.677062 0.367018 0.027 Uiso 1 1 calc R . . . .
H4B H 0.319480 0.827124 0.407600 0.027 Uiso 1 1 calc R . . . .
C5 C 0.1738(4) 0.8241(4) 0.5157(2) 0.0242(8) Uani 1 1 d . . . . .
H5A H 0.063010 0.785563 0.511452 0.029 Uiso 1 1 calc R . . . .
H5B H 0.184039 0.935348 0.552054 0.029 Uiso 1 1 calc R . . . .
C6 C 0.2884(4) 0.7515(4) 0.5806(2) 0.0196(7) Uani 1 1 d . . . . .
H6A H 0.264469 0.639992 0.549760 0.024 Uiso 1 1 calc R . . . .
H6B H 0.397981 0.774867 0.572159 0.024 Uiso 1 1 calc R . . . .
C7 C 0.1188(4) 0.7790(3) 0.7144(2) 0.0183(7) Uani 1 1 d . . . . .
H7A H 0.048486 0.833471 0.675943 0.022 Uiso 1 1 calc R . . . .
H7B H 0.116686 0.825454 0.791461 0.022 Uiso 1 1 calc R . . . .
C8 C 0.0528(4) 0.6123(3) 0.6766(2) 0.0200(7) Uani 1 1 d . . . . .
H8A H -0.064590 0.608054 0.668532 0.024 Uiso 1 1 calc R . . . .
H8B H 0.078458 0.560339 0.605220 0.024 Uiso 1 1 calc R . . . .
C9 C 0.1156(4) 0.5257(4) 0.7501(3) 0.0206(7) Uani 1 1 d . . . . .
H9A H 0.103893 0.584213 0.823905 0.025 Uiso 1 1 calc R . . . .
H9B H 0.051100 0.427276 0.727857 0.025 Uiso 1 1 calc R . . . .
C10 C 0.3478(4) 0.4185(3) 0.8234(2) 0.0188(7) Uani 1 1 d . . . . .
H10A H 0.303654 0.311019 0.794648 0.023 Uiso 1 1 calc R . . . .
H10B H 0.315408 0.466447 0.893206 0.023 Uiso 1 1 calc R . . . .
C11 C 0.5279(4) 0.4271(3) 0.8379(2) 0.0184(7) Uani 1 1 d . . . . .
H11A H 0.571505 0.381088 0.891823 0.022 Uiso 1 1 calc R . . . .
H11B H 0.560445 0.370270 0.769671 0.022 Uiso 1 1 calc R . . . .
C12 C 0.7635(4) 0.6103(3) 0.8756(3) 0.0201(7) Uani 1 1 d . . . . .
H12A H 0.786162 0.557056 0.803560 0.024 Uiso 1 1 calc R . . . .
H12B H 0.822407 0.564580 0.925434 0.024 Uiso 1 1 calc R . . . .
C13 C 0.8223(4) 0.7770(3) 0.9101(2) 0.0203(7) Uani 1 1 d . . . . .
H13A H 0.940049 0.785100 0.921579 0.024 Uiso 1 1 calc R . . . .
H13B H 0.791610 0.830141 0.979673 0.024 Uiso 1 1 calc R . . . .
C14 C 0.7620(4) 0.8601(3) 0.8335(2) 0.0194(7) Uani 1 1 d . . . . .
H14A H 0.823097 0.960406 0.856535 0.023 Uiso 1 1 calc R . . . .
H14B H 0.779814 0.801465 0.761092 0.023 Uiso 1 1 calc R . . . .
C15 C 0.5303(4) 0.9740(3) 0.7637(2) 0.0184(7) Uani 1 1 d . . . . .
H15A H 0.563287 0.936377 0.693314 0.022 Uiso 1 1 calc R . . . .
H15B H 0.573390 1.081154 0.799699 0.022 Uiso 1 1 calc R . . . .
C16 C 0.3497(4) 0.9614(3) 0.7495(2) 0.0175(7) Uani 1 1 d . . . . .
H16A H 0.317718 1.002964 0.820015 0.021 Uiso 1 1 calc R . . . .
H16B H 0.305363 1.021671 0.705200 0.021 Uiso 1 1 calc R . . . .
Cl2 Cl 0.69346(9) 0.70881(9) 0.50121(6) 0.0233(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 Cl1 2.5194(8) . ?
Ni1 O1 2.166(2) . ?
Ni1 N1 2.135(2) . ?
Ni1 N2 2.068(2) . ?
Ni1 N3 2.086(2) . ?
Ni1 N4 2.048(2) . ?
O1 H1A 0.826(18) . ?
O1 H1B 0.818(18) . ?
N1 C6 1.493(4) . ?
N1 C7 1.489(4) . ?
N1 C16 1.492(4) . ?
N2 H2 1.0000 . ?
N2 C9 1.477(4) . ?
N2 C10 1.490(4) . ?
N3 H3 1.0000 . ?
N3 C11 1.478(4) . ?
N3 C12 1.481(4) . ?
N4 H4 1.0000 . ?
N4 C14 1.471(4) . ?
N4 C15 1.482(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.196(4) . ?
C2 C3 1.445(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.542(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.522(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.529(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.533(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.520(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.517(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.520(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.523(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.521(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ni1 Cl1 170.46(6) . . ?
N1 Ni1 Cl1 94.63(6) . . ?
N1 Ni1 O1 94.91(8) . . ?
N2 Ni1 Cl1 90.36(7) . . ?
N2 Ni1 O1 88.52(9) . . ?
N2 Ni1 N1 95.96(10) . . ?
N2 Ni1 N3 85.16(10) . . ?
N3 Ni1 Cl1 84.32(7) . . ?
N3 Ni1 O1 86.15(9) . . ?
N3 Ni1 N1 178.47(10) . . ?
N4 Ni1 Cl1 86.83(7) . . ?
N4 Ni1 O1 93.99(9) . . ?
N4 Ni1 N1 85.86(9) . . ?
N4 Ni1 N2 176.78(10) . . ?
N4 Ni1 N3 92.98(10) . . ?
Ni1 O1 H1A 113(2) . . ?
Ni1 O1 H1B 129(2) . . ?
H1A O1 H1B 104(3) . . ?
C6 N1 Ni1 115.05(17) . . ?
C7 N1 Ni1 109.19(17) . . ?
C7 N1 C6 110.6(2) . . ?
C7 N1 C16 110.7(2) . . ?
C16 N1 Ni1 101.60(17) . . ?
C16 N1 C6 109.4(2) . . ?
Ni1 N2 H2 107.5 . . ?
C9 N2 Ni1 115.36(18) . . ?
C9 N2 H2 107.5 . . ?
C9 N2 C10 112.1(2) . . ?
C10 N2 Ni1 106.48(18) . . ?
C10 N2 H2 107.5 . . ?
Ni1 N3 H3 106.2 . . ?
C11 N3 Ni1 106.20(18) . . ?
C11 N3 H3 106.2 . . ?
C11 N3 C12 114.0(2) . . ?
C12 N3 Ni1 117.34(18) . . ?
C12 N3 H3 106.2 . . ?
Ni1 N4 H4 105.8 . . ?
C14 N4 Ni1 117.03(18) . . ?
C14 N4 H4 105.8 . . ?
C14 N4 C15 113.8(2) . . ?
C15 N4 Ni1 107.78(18) . . ?
C15 N4 H4 105.8 . . ?
C2 C1 H1 180.0 . . ?
C1 C2 C3 176.0(3) . . ?
C2 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
C2 C3 C4 113.9(3) . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C3 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C5 C4 C3 110.0(3) . . ?
C5 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 C6 110.9(3) . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
N1 C6 C5 115.8(2) . . ?
N1 C6 H6A 108.3 . . ?
N1 C6 H6B 108.3 . . ?
C5 C6 H6A 108.3 . . ?
C5 C6 H6B 108.3 . . ?
H6A C6 H6B 107.4 . . ?
N1 C7 H7A 108.9 . . ?
N1 C7 H7B 108.9 . . ?
N1 C7 C8 113.4(2) . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C7 C8 H8A 108.5 . . ?
C7 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C9 C8 C7 114.9(3) . . ?
C9 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
N2 C9 C8 112.1(2) . . ?
N2 C9 H9A 109.2 . . ?
N2 C9 H9B 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
N2 C10 H10A 109.8 . . ?
N2 C10 H10B 109.8 . . ?
N2 C10 C11 109.4(2) . . ?
H10A C10 H10B 108.2 . . ?
C11 C10 H10A 109.8 . . ?
C11 C10 H10B 109.8 . . ?
N3 C11 C10 108.9(2) . . ?
N3 C11 H11A 109.9 . . ?
N3 C11 H11B 109.9 . . ?
C10 C11 H11A 109.9 . . ?
C10 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
N3 C12 H12A 109.1 . . ?
N3 C12 H12B 109.1 . . ?
N3 C12 C13 112.3(2) . . ?
H12A C12 H12B 107.9 . . ?
C13 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C12 C13 H13A 108.2 . . ?
C12 C13 H13B 108.2 . . ?
C12 C13 C14 116.3(3) . . ?
H13A C13 H13B 107.4 . . ?
C14 C13 H13A 108.2 . . ?
C14 C13 H13B 108.2 . . ?
N4 C14 C13 111.6(2) . . ?
N4 C14 H14A 109.3 . . ?
N4 C14 H14B 109.3 . . ?
C13 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
N4 C15 H15A 110.1 . . ?
N4 C15 H15B 110.1 . . ?
N4 C15 C16 107.8(2) . . ?
H15A C15 H15B 108.5 . . ?
C16 C15 H15A 110.1 . . ?
C16 C15 H15B 110.1 . . ?
N1 C16 C15 110.4(2) . . ?
N1 C16 H16A 109.6 . . ?
N1 C16 H16B 109.6 . . ?
C15 C16 H16A 109.6 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?

_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_az193_a
_database_code_depnum_ccdc_archive 'CCDC 1580807'
_audit_update_record             
;
2017-10-19 deposited with the CCDC.
2018-03-27 downloaded from the CCDC.
;
_audit_creation_date             2017-08-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5375)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            '[Ni(II)(pentynyl-cyclam)]2+'
_chemical_name_systematic        Ni(pentynyl-cyclam)
_chemical_formula_moiety         'C15 H32 Cl N4 Ni O, Cl, C H2 Cl2'
_chemical_formula_sum            'C16 H34 Cl4 N4 Ni O'
_chemical_formula_weight         498.98
_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                   8.4321(6)
_cell_length_b                   12.0889(8)
_cell_length_c                   12.5339(9)
_cell_angle_alpha                106.833(2)
_cell_angle_beta                 100.100(3)
_cell_angle_gamma                107.515(2)
_cell_volume                     1116.93(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6785
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.47
_cell_measurement_theta_min      2.62
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.935
_exptl_absorpt_coefficient_mu    1.361
_exptl_absorpt_correction_T_max  0.0932
_exptl_absorpt_correction_T_min  0.0664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.1290 before and 0.0431 after correction. The Ratio of minimum to maximum transmission is 0.7124. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19269
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.487
_diffrn_reflns_theta_min         1.772
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3854
_reflns_number_total             4584
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_refine_diff_density_max         0.604
_refine_diff_density_min         -0.667
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         4584
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0300
_refine_ls_restrained_S_all      1.030
_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)+(0.0299P)²+0.7818P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0669
_refine_ls_wR_factor_ref         0.0714
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O1-H1A = O1-H1B
 0.84 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 N2(H2), N3(H3), N4(H4)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B),
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B),
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
3.c :
 C1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.81684(3) 0.71789(2) 0.79718(2) 0.01139(8) Uani 1 1 d . . . . .
Cl1 Cl 1.07736(6) 0.85152(5) 0.97099(4) 0.01491(12) Uani 1 1 d . . . . .
O1 O 0.57368(19) 0.59225(14) 0.66653(13) 0.0154(3) Uani 1 1 d D . . . .
H1A H 0.522(3) 0.614(2) 0.6191(19) 0.023 Uiso 1 1 d DR . . . .
H1B H 0.581(3) 0.5294(18) 0.627(2) 0.023 Uiso 1 1 d DR . . . .
N1 N 0.9438(2) 0.77153(16) 0.67560(14) 0.0135(4) Uani 1 1 d . . . . .
N2 N 0.7540(2) 0.87229(16) 0.81906(14) 0.0137(4) Uani 1 1 d . . . . .
H2 H 0.8376 0.9369 0.8939 0.016 Uiso 1 1 calc R . . . .
N3 N 0.6931(2) 0.66891(16) 0.91600(15) 0.0144(4) Uani 1 1 d . . . . .
H3 H 0.7745 0.7229 0.9953 0.017 Uiso 1 1 calc R . . . .
N4 N 0.8849(2) 0.56517(16) 0.78378(14) 0.0138(4) Uani 1 1 d . . . . .
H4 H 0.8056 0.4961 0.7099 0.017 Uiso 1 1 calc R . . . .
C1 C 0.9603(3) 0.7434(2) 0.19204(19) 0.0229(5) Uani 1 1 d . . . . .
H1 H 1.0228 0.7670 0.1410 0.027 Uiso 1 1 calc R . . . .
C2 C 0.8827(3) 0.7141(2) 0.25537(18) 0.0193(5) Uani 1 1 d . . . . .
C3 C 0.7985(3) 0.6817(2) 0.34168(18) 0.0172(5) Uani 1 1 d . . . . .
H3A H 0.7421 0.5900 0.3157 0.021 Uiso 1 1 calc R . . . .
H3B H 0.7073 0.7172 0.3476 0.021 Uiso 1 1 calc R . . . .
C4 C 0.9311(3) 0.7318(2) 0.46128(18) 0.0181(5) Uani 1 1 d . . . . .
H4A H 0.9905 0.8231 0.4863 0.022 Uiso 1 1 calc R . . . .
H4B H 1.0198 0.6938 0.4563 0.022 Uiso 1 1 calc R . . . .
C5 C 0.8405(3) 0.7015(2) 0.55096(17) 0.0155(4) Uani 1 1 d . . . . .
H5A H 0.7320 0.7180 0.5388 0.019 Uiso 1 1 calc R . . . .
H5B H 0.8076 0.6113 0.5356 0.019 Uiso 1 1 calc R . . . .
C6 C 0.9638(3) 0.90476(19) 0.70946(18) 0.0154(4) Uani 1 1 d . . . . .
H6A H 0.9937 0.9357 0.6478 0.019 Uiso 1 1 calc R . . . .
H6B H 1.0596 0.9551 0.7823 0.019 Uiso 1 1 calc R . . . .
C7 C 0.7961(3) 0.9193(2) 0.72739(18) 0.0164(4) Uani 1 1 d . . . . .
H7A H 0.8106 1.0082 0.7507 0.020 Uiso 1 1 calc R . . . .
H7B H 0.7006 0.8717 0.6540 0.020 Uiso 1 1 calc R . . . .
C8 C 0.5793(3) 0.8624(2) 0.83070(18) 0.0163(4) Uani 1 1 d . . . . .
H8A H 0.4906 0.8018 0.7574 0.020 Uiso 1 1 calc R . . . .
H8B H 0.5686 0.9444 0.8440 0.020 Uiso 1 1 calc R . . . .
C9 C 0.5458(3) 0.8210(2) 0.93118(18) 0.0172(5) Uani 1 1 d . . . . .
H9A H 0.4384 0.8316 0.9452 0.021 Uiso 1 1 calc R . . . .
H9B H 0.6426 0.8773 1.0021 0.021 Uiso 1 1 calc R . . . .
C10 C 0.5272(3) 0.6872(2) 0.91438(19) 0.0175(5) Uani 1 1 d . . . . .
H10A H 0.4844 0.6651 0.9770 0.021 Uiso 1 1 calc R . . . .
H10B H 0.4399 0.6306 0.8391 0.021 Uiso 1 1 calc R . . . .
C11 C 0.6795(3) 0.5405(2) 0.89984(19) 0.0171(5) Uani 1 1 d . . . . .
H11A H 0.5805 0.4810 0.8314 0.021 Uiso 1 1 calc R . . . .
H11B H 0.6593 0.5218 0.9693 0.021 Uiso 1 1 calc R . . . .
C12 C 0.8480(3) 0.5269(2) 0.88154(18) 0.0164(4) Uani 1 1 d . . . . .
H12A H 0.9449 0.5797 0.9533 0.020 Uiso 1 1 calc R . . . .
H12B H 0.8371 0.4392 0.8642 0.020 Uiso 1 1 calc R . . . .
C13 C 1.0656(3) 0.5842(2) 0.78031(18) 0.0165(4) Uani 1 1 d . . . . .
H13A H 1.0843 0.5052 0.7704 0.020 Uiso 1 1 calc R . . . .
H13B H 1.1469 0.6474 0.8553 0.020 Uiso 1 1 calc R . . . .
C14 C 1.1053(3) 0.6270(2) 0.68122(18) 0.0169(5) Uani 1 1 d . . . . .
H14A H 1.2171 0.6208 0.6723 0.020 Uiso 1 1 calc R . . . .
H14B H 1.0141 0.5687 0.6081 0.020 Uiso 1 1 calc R . . . .
C15 C 1.1164(3) 0.7593(2) 0.69629(18) 0.0159(4) Uani 1 1 d . . . . .
H15A H 1.1883 0.8157 0.7763 0.019 Uiso 1 1 calc R . . . .
H15B H 1.1757 0.7865 0.6416 0.019 Uiso 1 1 calc R . . . .
Cl2 Cl 0.36953(6) 0.64940(5) 0.47205(4) 0.01787(12) Uani 1 1 d . . . . .
Cl3 Cl 0.68428(9) 0.96632(7) 0.43987(6) 0.04235(19) Uani 1 1 d . . . . .
Cl4 Cl 0.47137(11) 0.81518(7) 0.20051(6) 0.04625(19) Uani 1 1 d . . . . .
C16 C 0.4721(3) 0.8784(3) 0.3463(2) 0.0330(6) Uani 1 1 d . . . . .
H16A H 0.4034 0.9323 0.3516 0.040 Uiso 1 1 calc R . . . .
H16B H 0.4161 0.8099 0.3717 0.040 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 Cl1 2.5157(6) . ?
Ni1 O1 2.1679(15) . ?
Ni1 N1 2.1483(17) . ?
Ni1 N2 2.0469(18) . ?
Ni1 N3 2.0838(17) . ?
Ni1 N4 2.0634(18) . ?
O1 H1A 0.828(16) . ?
O1 H1B 0.809(16) . ?
N1 C5 1.493(3) . ?
N1 C6 1.489(3) . ?
N1 C15 1.492(3) . ?
N2 H2 1.0000 . ?
N2 C7 1.473(3) . ?
N2 C8 1.478(3) . ?
N3 H3 1.0000 . ?
N3 C10 1.478(3) . ?
N3 C11 1.472(3) . ?
N4 H4 1.0000 . ?
N4 C12 1.479(3) . ?
N4 C13 1.482(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.178(3) . ?
C2 C3 1.475(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.531(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.534(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.523(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.524(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.524(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.527(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.528(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.527(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
Cl3 C16 1.762(3) . ?
Cl4 C16 1.762(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ni1 Cl1 170.94(4) . . ?
N1 Ni1 Cl1 94.11(5) . . ?
N1 Ni1 O1 94.91(6) . . ?
N2 Ni1 Cl1 87.07(5) . . ?
N2 Ni1 O1 94.34(6) . . ?
N2 Ni1 N1 86.01(7) . . ?
N2 Ni1 N3 92.97(7) . . ?
N2 Ni1 N4 177.22(7) . . ?
N3 Ni1 Cl1 85.67(5) . . ?
N3 Ni1 O1 85.32(6) . . ?
N3 Ni1 N1 178.97(7) . . ?
N4 Ni1 Cl1 90.63(5) . . ?
N4 Ni1 O1 87.68(6) . . ?
N4 Ni1 N1 95.73(7) . . ?
N4 Ni1 N3 85.28(7) . . ?
Ni1 O1 H1A 122.0(18) . . ?
Ni1 O1 H1B 112.1(18) . . ?
H1A O1 H1B 104(2) . . ?
C5 N1 Ni1 114.34(12) . . ?
C6 N1 Ni1 101.23(11) . . ?
C6 N1 C5 110.14(16) . . ?
C6 N1 C15 111.09(16) . . ?
C15 N1 Ni1 109.25(12) . . ?
C15 N1 C5 110.49(16) . . ?
Ni1 N2 H2 105.7 . . ?
C7 N2 Ni1 107.41(12) . . ?
C7 N2 H2 105.7 . . ?
C7 N2 C8 113.34(16) . . ?
C8 N2 Ni1 118.03(13) . . ?
C8 N2 H2 105.7 . . ?
Ni1 N3 H3 106.6 . . ?
C10 N3 Ni1 116.64(13) . . ?
C10 N3 H3 106.6 . . ?
C11 N3 Ni1 106.20(12) . . ?
C11 N3 H3 106.6 . . ?
C11 N3 C10 113.65(16) . . ?
Ni1 N4 H4 107.6 . . ?
C12 N4 Ni1 106.71(12) . . ?
C12 N4 H4 107.6 . . ?
C12 N4 C13 111.89(16) . . ?
C13 N4 Ni1 115.18(13) . . ?
C13 N4 H4 107.6 . . ?
C2 C1 H1 180.0 . . ?
C1 C2 C3 175.6(2) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 C4 110.92(18) . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C3 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
C3 C4 C5 110.28(17) . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
N1 C5 C4 115.86(17) . . ?
N1 C5 H5A 108.3 . . ?
N1 C5 H5B 108.3 . . ?
C4 C5 H5A 108.3 . . ?
C4 C5 H5B 108.3 . . ?
H5A C5 H5B 107.4 . . ?
N1 C6 H6A 109.6 . . ?
N1 C6 H6B 109.6 . . ?
N1 C6 C7 110.37(16) . . ?
H6A C6 H6B 108.1 . . ?
C7 C6 H6A 109.6 . . ?
C7 C6 H6B 109.6 . . ?
N2 C7 C6 108.54(17) . . ?
N2 C7 H7A 110.0 . . ?
N2 C7 H7B 110.0 . . ?
C6 C7 H7A 110.0 . . ?
C6 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
N2 C8 H8A 109.3 . . ?
N2 C8 H8B 109.3 . . ?
N2 C8 C9 111.45(17) . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C8 C9 H9A 108.3 . . ?
C8 C9 H9B 108.3 . . ?
C8 C9 C10 115.83(17) . . ?
H9A C9 H9B 107.4 . . ?
C10 C9 H9A 108.3 . . ?
C10 C9 H9B 108.3 . . ?
N3 C10 C9 112.24(17) . . ?
N3 C10 H10A 109.2 . . ?
N3 C10 H10B 109.2 . . ?
C9 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
N3 C11 H11A 109.9 . . ?
N3 C11 H11B 109.9 . . ?
N3 C11 C12 108.98(17) . . ?
H11A C11 H11B 108.3 . . ?
C12 C11 H11A 109.9 . . ?
C12 C11 H11B 109.9 . . ?
N4 C12 C11 109.51(17) . . ?
N4 C12 H12A 109.8 . . ?
N4 C12 H12B 109.8 . . ?
C11 C12 H12A 109.8 . . ?
C11 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
N4 C13 H13A 109.2 . . ?
N4 C13 H13B 109.2 . . ?
N4 C13 C14 111.96(17) . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
C13 C14 H14A 108.4 . . ?
C13 C14 H14B 108.4 . . ?
H14A C14 H14B 107.5 . . ?
C15 C14 C13 115.48(17) . . ?
C15 C14 H14A 108.4 . . ?
C15 C14 H14B 108.4 . . ?
N1 C15 C14 113.61(17) . . ?
N1 C15 H15A 108.8 . . ?
N1 C15 H15B 108.8 . . ?
C14 C15 H15A 108.8 . . ?
C14 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
Cl3 C16 Cl4 111.88(14) . . ?
Cl3 C16 H16A 109.2 . . ?
Cl3 C16 H16B 109.2 . . ?
Cl4 C16 H16A 109.2 . . ?
Cl4 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?

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
O1 H1A Cl2 0.828(16) 2.276(17) 3.0987(16) 173(2) .
O1 H1B Cl2 0.809(16) 2.353(17) 3.1584(16) 173(2) 2_666

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 N1 C5 C4 -176.58(14) . . . . ?
Ni1 N1 C6 C7 -44.96(17) . . . . ?
Ni1 N1 C15 C14 60.23(18) . . . . ?
Ni1 N2 C7 C6 -38.32(18) . . . . ?
Ni1 N2 C8 C9 56.7(2) . . . . ?
Ni1 N3 C10 C9 -55.8(2) . . . . ?
Ni1 N3 C11 C12 40.53(18) . . . . ?
Ni1 N4 C12 C11 38.96(18) . . . . ?
Ni1 N4 C13 C14 -56.4(2) . . . . ?
N1 C6 C7 N2 59.0(2) . . . . ?
N2 C8 C9 C10 -69.0(2) . . . . ?
N3 C11 C12 N4 -54.8(2) . . . . ?
N4 C13 C14 C15 70.1(2) . . . . ?
C2 C3 C4 C5 177.92(18) . . . . ?
C3 C4 C5 N1 -164.91(18) . . . . ?
C5 N1 C6 C7 76.4(2) . . . . ?
C5 N1 C15 C14 -66.4(2) . . . . ?
C6 N1 C5 C4 70.2(2) . . . . ?
C6 N1 C15 C14 171.07(16) . . . . ?
C7 N2 C8 C9 -176.54(17) . . . . ?
C8 N2 C7 C6 -170.52(16) . . . . ?
C8 C9 C10 N3 69.4(2) . . . . ?
C10 N3 C11 C12 170.10(16) . . . . ?
C11 N3 C10 C9 -179.93(17) . . . . ?
C12 N4 C13 C14 -178.54(17) . . . . ?
C13 N4 C12 C11 165.79(17) . . . . ?
C13 C14 C15 N1 -75.3(2) . . . . ?
C15 N1 C5 C4 -52.9(2) . . . . ?
C15 N1 C6 C7 -160.86(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
