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

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1436243'
_audit_update_record             
;
2015-11-10 deposited with the CCDC.
2016-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H28 Br N4 Ni O2, Br'
_chemical_formula_sum            'C18 H28 Br2 N4 Ni O2'
_chemical_formula_weight         550.97

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.2476(5)
_cell_length_b                   9.8870(6)
_cell_length_c                   12.5210(7)
_cell_angle_alpha                92.876(3)
_cell_angle_beta                 90.579(3)
_cell_angle_gamma                110.439(4)
_cell_volume                     1070.92(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4168
_cell_measurement_theta_min      1.6
_cell_measurement_theta_max      26.2

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_F_000             556
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    4.657
_shelx_estimated_absorpt_T_min   0.472
_shelx_estimated_absorpt_T_max   0.836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4718
_exptl_absorpt_correction_T_max  0.8358
_exptl_absorpt_process_details   'SADABS, Bruker 2012'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microsource'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15692
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.629
_diffrn_reflns_theta_max         26.161
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             4168
_reflns_number_gt                3547
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2012)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2012)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2012)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'WinGX (Farrugia, 2012)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0350P)²+1.4143P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4168
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0840
_refine_ls_wR_factor_gt          0.0803
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.125
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6671(4) 0.0793(4) 0.6784(3) 0.0204(7) Uani 1 1 d . . . . .
H6 H 0.6031 0.0663 0.6161 0.025 Uiso 1 1 calc R U . . .
C2 C 0.7602(4) -0.0018(4) 0.6847(3) 0.0226(8) Uani 1 1 d . . . . .
H3 H 0.7606 -0.0689 0.6278 0.027 Uiso 1 1 calc R U . . .
C3 C 0.8538(4) 0.0154(4) 0.7751(3) 0.0241(8) Uani 1 1 d . . . . .
H5 H 0.9189 -0.0401 0.7815 0.029 Uiso 1 1 calc R U . . .
C4 C 0.8507(4) 0.1148(4) 0.8559(3) 0.0222(8) Uani 1 1 d . . . . .
H4 H 0.9135 0.1284 0.9188 0.027 Uiso 1 1 calc R U . . .
C5 C 0.7545(4) 0.1950(4) 0.8441(3) 0.0188(7) Uani 1 1 d . . . . .
C6 C 0.7519(4) 0.3075(4) 0.9291(3) 0.0197(7) Uani 1 1 d . . . . .
H1 H 0.7428 0.2654 0.9999 0.024 Uiso 1 1 calc R U . . .
H2 H 0.8510 0.3898 0.9295 0.024 Uiso 1 1 calc R U . . .
C7 C 0.4990(4) 0.3089(4) 0.9895(3) 0.0209(8) Uani 1 1 d . . . . .
H14 H 0.4316 0.3677 0.9878 0.025 Uiso 1 1 calc R U . . .
H15 H 0.5438 0.3187 1.0629 0.025 Uiso 1 1 calc R U . . .
C8 C 0.4049(4) 0.1528(4) 0.9611(3) 0.0222(8) Uani 1 1 d . . . . .
H12 H 0.4682 0.0915 0.9712 0.027 Uiso 1 1 calc R U . . .
H13 H 0.3145 0.1198 1.0074 0.027 Uiso 1 1 calc R U . . .
C9 C 0.2793(5) -0.0056(4) 0.8144(3) 0.0329(10) Uani 1 1 d . . . . .
H9 H 0.3525 -0.0570 0.8168 0.049 Uiso 1 1 calc R U . . .
H10 H 0.2408 -0.0097 0.7406 0.049 Uiso 1 1 calc R U . . .
H11 H 0.1925 -0.0513 0.8603 0.049 Uiso 1 1 calc R U . . .
C10 C 0.2551(4) 0.4092(4) 0.8159(3) 0.0238(8) Uani 1 1 d . . . . .
H16 H 0.2165 0.3264 0.8569 0.029 Uiso 1 1 calc R U . . .
C11 C 0.1702(4) 0.4976(4) 0.8076(3) 0.0272(9) Uani 1 1 d . . . . .
H30 H 0.0750 0.4760 0.8430 0.033 Uiso 1 1 calc R U . . .
C12 C 0.2234(4) 0.6185(4) 0.7476(3) 0.0256(8) Uani 1 1 d . . . . .
H29 H 0.1654 0.6803 0.7402 0.031 Uiso 1 1 calc R U . . .
C13 C 0.3646(4) 0.6466(4) 0.6985(3) 0.0215(8) Uani 1 1 d . . . . .
H17 H 0.4054 0.7291 0.6574 0.026 Uiso 1 1 calc R U . . .
C14 C 0.4447(4) 0.5530(4) 0.7101(3) 0.0184(7) Uani 1 1 d . . . . .
C15 C 0.5892(4) 0.5728(4) 0.6501(3) 0.0251(8) Uani 1 1 d . . . . .
H27 H 0.5617 0.5472 0.5733 0.030 Uiso 1 1 calc R U . . .
H28 H 0.6558 0.6761 0.6571 0.030 Uiso 1 1 calc R U . . .
C16 C 0.7767(4) 0.4566(5) 0.6053(3) 0.0312(9) Uani 1 1 d . . . . .
H24 H 0.7139 0.3714 0.5594 0.037 Uiso 1 1 calc R U . . .
H25 H 0.8576 0.4302 0.6420 0.037 Uiso 1 1 calc R U . . .
C17 C 0.8560(4) 0.5804(4) 0.5330(3) 0.0292(9) Uani 1 1 d . . . . .
H22 H 0.9186 0.5497 0.4799 0.035 Uiso 1 1 calc R U . . .
H23 H 0.7775 0.6077 0.4940 0.035 Uiso 1 1 calc R U . . .
C18 C 1.0323(5) 0.8166(5) 0.5345(4) 0.0426(11) Uani 1 1 d . . . . .
H19 H 1.1082 0.7907 0.4920 0.064 Uiso 1 1 calc R U . . .
H20 H 1.0855 0.9026 0.5813 0.064 Uiso 1 1 calc R U . . .
H21 H 0.9589 0.8369 0.4866 0.064 Uiso 1 1 calc R U . . .
N1 N 0.6619(3) 0.1774(3) 0.7568(2) 0.0166(6) Uani 1 1 d . . . . .
N2 N 0.6237(3) 0.3619(3) 0.9132(2) 0.0174(6) Uani 1 1 d . . . . .
N3 N 0.3920(3) 0.4357(3) 0.7677(2) 0.0172(6) Uani 1 1 d . . . . .
N4 N 0.6765(3) 0.4862(3) 0.6870(2) 0.0220(7) Uani 1 1 d . . . . .
O1 O 0.3554(3) 0.1426(3) 0.85146(18) 0.0210(5) Uani 1 1 d . . . . .
O2 O 0.9513(3) 0.6991(4) 0.5981(2) 0.0446(9) Uani 1 1 d . . . . .
Ni1 Ni 0.52411(4) 0.30352(5) 0.75750(3) 0.01633(12) Uani 1 1 d . . . . .
Br1 Br 0.38505(4) 0.19461(4) 0.58072(3) 0.02325(11) Uani 1 1 d . . . . .
Br2 Br 0.88748(4) 0.69655(4) 0.90783(3) 0.02166(11) Uani 1 1 d . . . . .
H101 H 0.660(4) 0.450(4) 0.924(3) 0.013(9) Uiso 1 1 d . . . . .
H102 H 0.747(5) 0.556(5) 0.735(3) 0.042(13) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.358(4) . ?
C1 C2 1.371(5) . ?
C1 H6 0.9500 . ?
C2 C3 1.384(5) . ?
C2 H3 0.9500 . ?
C3 C4 1.382(5) . ?
C3 H5 0.9500 . ?
C4 C5 1.394(5) . ?
C4 H4 0.9500 . ?
C5 N1 1.348(4) . ?
C5 C6 1.507(5) . ?
C6 N2 1.479(4) . ?
C6 H1 0.9900 . ?
C6 H2 0.9900 . ?
C7 N2 1.473(4) . ?
C7 C8 1.506(5) . ?
C7 H14 0.9900 . ?
C7 H15 0.9900 . ?
C8 O1 1.431(4) . ?
C8 H12 0.9900 . ?
C8 H13 0.9900 . ?
C9 O1 1.437(4) . ?
C9 H9 0.9800 . ?
C9 H10 0.9800 . ?
C9 H11 0.9800 . ?
C10 N3 1.355(4) . ?
C10 C11 1.370(5) . ?
C10 H16 0.9500 . ?
C11 C12 1.387(5) . ?
C11 H30 0.9500 . ?
C12 C13 1.393(5) . ?
C12 H29 0.9500 . ?
C13 C14 1.385(5) . ?
C13 H17 0.9500 . ?
C14 N3 1.341(4) . ?
C14 C15 1.498(5) . ?
C15 N4 1.453(5) . ?
C15 H27 0.9900 . ?
C15 H28 0.9900 . ?
C16 N4 1.472(5) . ?
C16 C17 1.534(5) . ?
C16 H24 0.9900 . ?
C16 H25 0.9900 . ?
C17 O2 1.409(5) . ?
C17 H22 0.9900 . ?
C17 H23 0.9900 . ?
C18 O2 1.429(5) . ?
C18 H19 0.9800 . ?
C18 H20 0.9800 . ?
C18 H21 0.9800 . ?
N1 Ni1 2.071(3) . ?
N2 Ni1 2.112(3) . ?
N2 H101 0.82(4) . ?
N3 Ni1 2.078(3) . ?
N4 Ni1 2.106(3) . ?
N4 H102 0.95(5) . ?
O1 Ni1 2.200(2) . ?
Ni1 Br1 2.5394(5) . ?

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
N1 C1 C2 123.2(3) . . ?
N1 C1 H6 118.4 . . ?
C2 C1 H6 118.4 . . ?
C1 C2 C3 119.2(3) . . ?
C1 C2 H3 120.4 . . ?
C3 C2 H3 120.4 . . ?
C4 C3 C2 118.7(3) . . ?
C4 C3 H5 120.7 . . ?
C2 C3 H5 120.7 . . ?
C3 C4 C5 119.4(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 122.1(3) . . ?
N1 C5 C6 117.1(3) . . ?
C4 C5 C6 120.8(3) . . ?
N2 C6 C5 113.1(3) . . ?
N2 C6 H1 109.0 . . ?
C5 C6 H1 109.0 . . ?
N2 C6 H2 109.0 . . ?
C5 C6 H2 109.0 . . ?
H1 C6 H2 107.8 . . ?
N2 C7 C8 110.0(3) . . ?
N2 C7 H14 109.7 . . ?
C8 C7 H14 109.7 . . ?
N2 C7 H15 109.7 . . ?
C8 C7 H15 109.7 . . ?
H14 C7 H15 108.2 . . ?
O1 C8 C7 107.4(3) . . ?
O1 C8 H12 110.2 . . ?
C7 C8 H12 110.2 . . ?
O1 C8 H13 110.2 . . ?
C7 C8 H13 110.2 . . ?
H12 C8 H13 108.5 . . ?
O1 C9 H9 109.5 . . ?
O1 C9 H10 109.5 . . ?
H9 C9 H10 109.5 . . ?
O1 C9 H11 109.5 . . ?
H9 C9 H11 109.5 . . ?
H10 C9 H11 109.5 . . ?
N3 C10 C11 122.4(3) . . ?
N3 C10 H16 118.8 . . ?
C11 C10 H16 118.8 . . ?
C10 C11 C12 119.9(3) . . ?
C10 C11 H30 120.0 . . ?
C12 C11 H30 120.0 . . ?
C11 C12 C13 117.9(4) . . ?
C11 C12 H29 121.0 . . ?
C13 C12 H29 121.0 . . ?
C14 C13 C12 119.3(3) . . ?
C14 C13 H17 120.4 . . ?
C12 C13 H17 120.4 . . ?
N3 C14 C13 122.5(3) . . ?
N3 C14 C15 116.9(3) . . ?
C13 C14 C15 120.4(3) . . ?
N4 C15 C14 113.6(3) . . ?
N4 C15 H27 108.8 . . ?
C14 C15 H27 108.8 . . ?
N4 C15 H28 108.8 . . ?
C14 C15 H28 108.8 . . ?
H27 C15 H28 107.7 . . ?
N4 C16 C17 116.0(3) . . ?
N4 C16 H24 108.3 . . ?
C17 C16 H24 108.3 . . ?
N4 C16 H25 108.3 . . ?
C17 C16 H25 108.3 . . ?
H24 C16 H25 107.4 . . ?
O2 C17 C16 108.1(3) . . ?
O2 C17 H22 110.1 . . ?
C16 C17 H22 110.1 . . ?
O2 C17 H23 110.1 . . ?
C16 C17 H23 110.1 . . ?
H22 C17 H23 108.4 . . ?
O2 C18 H19 109.5 . . ?
O2 C18 H20 109.5 . . ?
H19 C18 H20 109.5 . . ?
O2 C18 H21 109.5 . . ?
H19 C18 H21 109.5 . . ?
H20 C18 H21 109.5 . . ?
C5 N1 C1 117.5(3) . . ?
C5 N1 Ni1 115.8(2) . . ?
C1 N1 Ni1 126.7(2) . . ?
C7 N2 C6 113.6(3) . . ?
C7 N2 Ni1 107.55(19) . . ?
C6 N2 Ni1 111.1(2) . . ?
C7 N2 H101 106(2) . . ?
C6 N2 H101 107(2) . . ?
Ni1 N2 H101 111(2) . . ?
C14 N3 C10 118.1(3) . . ?
C14 N3 Ni1 113.9(2) . . ?
C10 N3 Ni1 127.7(2) . . ?
C15 N4 C16 113.5(3) . . ?
C15 N4 Ni1 108.7(2) . . ?
C16 N4 Ni1 115.6(3) . . ?
C15 N4 H102 99(3) . . ?
C16 N4 H102 103(3) . . ?
Ni1 N4 H102 115(3) . . ?
C8 O1 C9 110.9(3) . . ?
C8 O1 Ni1 111.81(18) . . ?
C9 O1 Ni1 123.5(2) . . ?
C17 O2 C18 110.7(3) . . ?
N1 Ni1 N3 176.36(10) . . ?
N1 Ni1 N4 99.00(11) . . ?
N3 Ni1 N4 80.98(11) . . ?
N1 Ni1 N2 81.09(11) . . ?
N3 Ni1 N2 95.29(11) . . ?
N4 Ni1 N2 95.38(12) . . ?
N1 Ni1 O1 89.10(10) . . ?
N3 Ni1 O1 90.48(10) . . ?
N4 Ni1 O1 169.21(11) . . ?
N2 Ni1 O1 78.76(10) . . ?
N1 Ni1 Br1 95.11(7) . . ?
N3 Ni1 Br1 88.52(7) . . ?
N4 Ni1 Br1 93.09(8) . . ?
N2 Ni1 Br1 171.17(9) . . ?
O1 Ni1 Br1 93.27(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.3(5) . . . . ?
C1 C2 C3 C4 -0.4(5) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C3 C4 C5 N1 1.1(5) . . . . ?
C3 C4 C5 C6 -178.1(3) . . . . ?
N1 C5 C6 N2 11.5(4) . . . . ?
C4 C5 C6 N2 -169.2(3) . . . . ?
N2 C7 C8 O1 -53.9(4) . . . . ?
N3 C10 C11 C12 0.5(5) . . . . ?
C10 C11 C12 C13 -0.9(5) . . . . ?
C11 C12 C13 C14 0.8(5) . . . . ?
C12 C13 C14 N3 -0.3(5) . . . . ?
C12 C13 C14 C15 174.3(3) . . . . ?
N3 C14 C15 N4 -17.1(4) . . . . ?
C13 C14 C15 N4 167.9(3) . . . . ?
N4 C16 C17 O2 61.0(4) . . . . ?
C4 C5 N1 C1 -1.2(5) . . . . ?
C6 C5 N1 C1 178.0(3) . . . . ?
C4 C5 N1 Ni1 178.4(2) . . . . ?
C6 C5 N1 Ni1 -2.4(4) . . . . ?
C2 C1 N1 C5 0.5(5) . . . . ?
C2 C1 N1 Ni1 -179.0(2) . . . . ?
C8 C7 N2 C6 -74.2(3) . . . . ?
C8 C7 N2 Ni1 49.2(3) . . . . ?
C5 C6 N2 C7 106.9(3) . . . . ?
C5 C6 N2 Ni1 -14.5(3) . . . . ?
C13 C14 N3 C10 -0.1(5) . . . . ?
C15 C14 N3 C10 -174.9(3) . . . . ?
C13 C14 N3 Ni1 173.7(2) . . . . ?
C15 C14 N3 Ni1 -1.2(4) . . . . ?
C11 C10 N3 C14 0.0(5) . . . . ?
C11 C10 N3 Ni1 -172.8(3) . . . . ?
C14 C15 N4 C16 155.8(3) . . . . ?
C14 C15 N4 Ni1 25.6(4) . . . . ?
C17 C16 N4 C15 37.7(5) . . . . ?
C17 C16 N4 Ni1 164.4(3) . . . . ?
C7 C8 O1 C9 173.5(3) . . . . ?
C7 C8 O1 Ni1 31.4(3) . . . . ?
C16 C17 O2 C18 178.1(3) . . . . ?

_refine_diff_density_max         0.905
_refine_diff_density_min         -0.972
_refine_diff_density_rms         0.108

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1436244'
_audit_update_record             
;
2015-11-10 deposited with the CCDC.
2016-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H24 N4 Ni O2, 2(Br), 2(H2 O)'
_chemical_formula_sum            'C16 H28 Br2 N4 Ni O4'
_chemical_formula_weight         558.91

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.1950(4)
_cell_length_b                   8.3725(4)
_cell_length_c                   8.9081(4)
_cell_angle_alpha                109.596(2)
_cell_angle_beta                 98.327(2)
_cell_angle_gamma                101.729(2)
_cell_volume                     548.55(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2119
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      26.1

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_F_000             282
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    4.554
_shelx_estimated_absorpt_T_min   0.478
_shelx_estimated_absorpt_T_max   0.839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2570
_exptl_absorpt_correction_T_max  0.6947
_exptl_absorpt_process_details   'SADABS, Bruker 2012'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microsource'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7914
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.494
_diffrn_reflns_theta_max         26.087
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             2119
_reflns_number_gt                1955
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2012)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2012)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2012)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'WinGX (Farrugia, 2012)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0338P)²+0.3159P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2119
_refine_ls_number_parameters     140
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0240
_refine_ls_wR_factor_ref         0.0629
_refine_ls_wR_factor_gt          0.0616
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Br2 Br 0.28354(3) 0.31066(3) 0.07519(3) 0.02125(10) Uani 1 1 d . . . . .
Ni1 Ni 0.0000 0.0000 0.5000 0.01230(11) Uani 1 2 d S . P . .
O1W O 0.5161(2) 0.7253(3) 0.2221(2) 0.0250(4) Uani 1 1 d . . . . .
C1 C 0.1988(3) -0.1360(3) 0.7303(3) 0.0183(5) Uani 1 1 d . . . . .
H1 H 0.1898 -0.0373 0.8176 0.022 Uiso 1 1 calc R U . . .
O1 O -0.2409(2) -0.1507(2) 0.5001(2) 0.0182(4) Uani 1 1 d . . . . .
N2 N 0.0217(2) -0.1619(3) 0.2727(2) 0.0148(4) Uani 1 1 d . . . . .
N1 N 0.1233(2) -0.1632(3) 0.5755(2) 0.0151(4) Uani 1 1 d . . . . .
C8 C -0.3094(3) -0.0457(3) 0.6267(3) 0.0209(5) Uani 1 1 d . . . . .
H8A H -0.3975 -0.1224 0.6559 0.025 Uiso 1 1 calc R U . . .
H8B H -0.3628 0.0340 0.5885 0.025 Uiso 1 1 calc R U . . .
C7 C 0.1621(3) -0.0598(3) 0.2268(3) 0.0205(5) Uani 1 1 d . . . . .
H7B H 0.1187 0.0207 0.1818 0.025 Uiso 1 1 calc R U . . .
H7A H 0.2026 -0.1413 0.1407 0.025 Uiso 1 1 calc R U . . .
C6 C 0.0490(3) -0.3279(3) 0.2816(3) 0.0191(5) Uani 1 1 d . . . . .
H6B H 0.1201 -0.3724 0.2048 0.023 Uiso 1 1 calc R U . . .
H6A H -0.0629 -0.4172 0.2472 0.023 Uiso 1 1 calc R U . . .
C5 C 0.1365(3) -0.3029(3) 0.4531(3) 0.0154(5) Uani 1 1 d . . . . .
C2 C 0.2889(3) -0.2466(3) 0.7665(3) 0.0196(5) Uani 1 1 d . . . . .
H2 H 0.3419 -0.2233 0.8765 0.024 Uiso 1 1 calc R U . . .
C3 C 0.3006(3) -0.3915(3) 0.6399(3) 0.0210(5) Uani 1 1 d . . . . .
H3 H 0.3617 -0.4692 0.6620 0.025 Uiso 1 1 calc R U . . .
C4 C 0.2221(3) -0.4220(3) 0.4803(3) 0.0201(5) Uani 1 1 d . . . . .
H4 H 0.2265 -0.5219 0.3915 0.024 Uiso 1 1 calc R U . . .
H2W H 0.556(6) 0.716(6) 0.144(5) 0.070(14) Uiso 1 1 d . . . . .
H1W H 0.453(5) 0.621(5) 0.190(4) 0.042(10) Uiso 1 1 d . . . . .
H101 H -0.062(3) -0.193(3) 0.197(3) 0.013(6) Uiso 1 1 d . . . . .
H102 H -0.303(4) -0.177(4) 0.428(4) 0.022(8) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N1 2.0792(18) 2_556 ?
Ni1 N1 2.0792(18) . ?
Ni1 N2 2.0806(19) . ?
Ni1 N2 2.0806(19) 2_556 ?
Ni1 O1 2.1161(17) 2_556 ?
Ni1 O1 2.1161(17) . ?
O1W H2W 0.80(5) . ?
O1W H1W 0.85(4) . ?
C1 N1 1.349(3) . ?
C1 C2 1.384(3) . ?
C1 H1 0.9500 . ?
O1 C8 1.442(3) . ?
O1 H102 0.70(3) . ?
N2 C6 1.477(3) . ?
N2 C7 1.481(3) . ?
N2 H101 0.82(3) . ?
N1 C5 1.341(3) . ?
C8 C7 1.509(3) 2_556 ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C7 C8 1.509(3) 2_556 ?
C7 H7B 0.9900 . ?
C7 H7A 0.9900 . ?
C6 C5 1.516(3) . ?
C6 H6B 0.9900 . ?
C6 H6A 0.9900 . ?
C5 C4 1.394(3) . ?
C2 C3 1.383(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(3) . ?
C3 H3 0.9500 . ?
C4 H4 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
N1 Ni1 N1 180.0 2_556 . ?
N1 Ni1 N2 98.71(7) 2_556 . ?
N1 Ni1 N2 81.29(7) . . ?
N1 Ni1 N2 81.29(7) 2_556 2_556 ?
N1 Ni1 N2 98.71(7) . 2_556 ?
N2 Ni1 N2 180.0 . 2_556 ?
N1 Ni1 O1 91.06(7) 2_556 2_556 ?
N1 Ni1 O1 88.94(7) . 2_556 ?
N2 Ni1 O1 82.50(7) . 2_556 ?
N2 Ni1 O1 97.50(7) 2_556 2_556 ?
N1 Ni1 O1 88.94(7) 2_556 . ?
N1 Ni1 O1 91.06(7) . . ?
N2 Ni1 O1 97.50(7) . . ?
N2 Ni1 O1 82.50(7) 2_556 . ?
O1 Ni1 O1 180.0 2_556 . ?
H2W O1W H1W 99(4) . . ?
N1 C1 C2 122.3(2) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C8 O1 Ni1 109.28(14) . . ?
C8 O1 H102 105(2) . . ?
Ni1 O1 H102 115(3) . . ?
C6 N2 C7 113.99(18) . . ?
C6 N2 Ni1 109.61(14) . . ?
C7 N2 Ni1 107.02(15) . . ?
C6 N2 H101 104.8(18) . . ?
C7 N2 H101 105.5(18) . . ?
Ni1 N2 H101 116.0(18) . . ?
C5 N1 C1 118.44(19) . . ?
C5 N1 Ni1 114.51(14) . . ?
C1 N1 Ni1 126.89(16) . . ?
O1 C8 C7 107.26(19) . 2_556 ?
O1 C8 H8A 110.3 . . ?
C7 C8 H8A 110.3 2_556 . ?
O1 C8 H8B 110.3 . . ?
C7 C8 H8B 110.3 2_556 . ?
H8A C8 H8B 108.5 . . ?
N2 C7 C8 110.85(19) . 2_556 ?
N2 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 2_556 . ?
N2 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 2_556 . ?
H7B C7 H7A 108.1 . . ?
N2 C6 C5 111.81(19) . . ?
N2 C6 H6B 109.3 . . ?
C5 C6 H6B 109.3 . . ?
N2 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
H6B C6 H6A 107.9 . . ?
N1 C5 C4 122.5(2) . . ?
N1 C5 C6 116.3(2) . . ?
C4 C5 C6 121.2(2) . . ?
C3 C2 C1 119.0(2) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 119.2(2) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 118.5(2) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 N1 C5 0.1(3) . . . . ?
C2 C1 N1 Ni1 -175.03(17) . . . . ?
Ni1 O1 C8 C7 -39.5(2) . . . 2_556 ?
C6 N2 C7 C8 -81.0(2) . . . 2_556 ?
Ni1 N2 C7 C8 40.4(2) . . . 2_556 ?
C7 N2 C6 C5 92.3(2) . . . . ?
Ni1 N2 C6 C5 -27.6(2) . . . . ?
C1 N1 C5 C4 1.3(3) . . . . ?
Ni1 N1 C5 C4 176.98(17) . . . . ?
C1 N1 C5 C6 179.8(2) . . . . ?
Ni1 N1 C5 C6 -4.5(2) . . . . ?
N2 C6 C5 N1 21.8(3) . . . . ?
N2 C6 C5 C4 -159.6(2) . . . . ?
N1 C1 C2 C3 -0.8(4) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C2 C3 C4 C5 1.2(4) . . . . ?
N1 C5 C4 C3 -1.9(4) . . . . ?
C6 C5 C4 C3 179.6(2) . . . . ?

_refine_diff_density_max         0.626
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.083

