# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cu

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'Cu (C9 H9 Br N O)2'
_chemical_formula_sum            'C18 H18 Br2 Cu N2 O2'
_chemical_formula_weight         517.70

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'
Cu Cu 0.3201 1.2651 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   10.2397(8)
_cell_length_b                   10.0932(6)
_cell_length_c                   8.7855(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.225(7)
_cell_angle_gamma                90.00
_cell_volume                     887.40(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2264
_cell_measurement_theta_min      2.8605
_cell_measurement_theta_max      27.4859

_exptl_crystal_description       prism
_exptl_crystal_colour            'olive green'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.937
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             510
_exptl_absorpt_coefficient_mu    5.748
_exptl_absorpt_correction_T_min  0.3927
_exptl_absorpt_correction_T_max  0.7620
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis PRO (Agilent, 2013)'

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  
'Agilent Technologies SuperNova Dual diffractometer with Atlas detector'
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measurement_method       'ω scan'
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5938
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         27.55
_reflns_number_total             2059
_reflns_number_gt                1808
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'CrysAlis PRO (Agilent, 2013)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2013)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'X-Seed (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0282P)²+0.4931P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2059
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0659
_refine_ls_wR_factor_gt          0.0612
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.27979(3) 0.93546(3) 0.64885(3) 0.02266(10) Uani 1 1 d . . .
Cu1 Cu 0.5000 0.5000 0.5000 0.01195(12) Uani 1 2 d S . .
O1 O 0.63980(19) 0.46051(17) 0.3961(2) 0.0170(4) Uani 1 1 d . . .
N1 N 0.5748(2) 0.6817(2) 0.5562(2) 0.0123(4) Uani 1 1 d . . .
C1 C 0.7477(3) 0.5278(2) 0.3879(3) 0.0128(5) Uani 1 1 d . . .
C2 C 0.8408(3) 0.4708(3) 0.3085(3) 0.0158(5) Uani 1 1 d . . .
H2 H 0.822(3) 0.384(3) 0.272(3) 0.019 Uiso 1 1 d . . .
C3 C 0.9537(3) 0.5376(3) 0.2917(3) 0.0179(6) Uani 1 1 d . . .
H3 H 1.013(3) 0.496(3) 0.239(3) 0.021 Uiso 1 1 d . . .
C4 C 0.9813(3) 0.6649(3) 0.3532(3) 0.0182(6) Uani 1 1 d . . .
H4 H 1.060(3) 0.705(3) 0.350(3) 0.022 Uiso 1 1 d . . .
C5 C 0.8938(3) 0.7216(3) 0.4328(3) 0.0164(5) Uani 1 1 d . . .
H5 H 0.915(3) 0.805(3) 0.479(3) 0.020 Uiso 1 1 d . . .
C6 C 0.7765(3) 0.6560(2) 0.4513(3) 0.0126(5) Uani 1 1 d . . .
C7 C 0.6884(3) 0.7241(2) 0.5327(3) 0.0130(5) Uani 1 1 d . . .
H7 H 0.722(3) 0.807(3) 0.576(3) 0.016 Uiso 1 1 d . . .
C8 C 0.5033(3) 0.7740(3) 0.6394(3) 0.0138(5) Uani 1 1 d . . .
H8A H 0.564(3) 0.846(3) 0.686(3) 0.017 Uiso 1 1 d . . .
H8B H 0.481(3) 0.724(3) 0.725(3) 0.017 Uiso 1 1 d . . .
C9 C 0.3817(3) 0.8279(3) 0.5293(3) 0.0156(5) Uani 1 1 d . . .
H9A H 0.323(3) 0.763(3) 0.485(3) 0.019 Uiso 1 1 d . . .
H9B H 0.400(3) 0.886(3) 0.447(3) 0.019 Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.02328(18) 0.02214(16) 0.02479(16) -0.00054(11) 0.01010(12) 0.00945(12)
Cu1 0.0114(2) 0.0098(2) 0.0159(2) -0.00046(16) 0.00594(17) -0.00021(17)
O1 0.0146(10) 0.0132(8) 0.0262(10) -0.0017(8) 0.0112(8) -0.0016(8)
N1 0.0114(11) 0.0119(9) 0.0141(10) -0.0003(8) 0.0037(8) 0.0023(9)
C1 0.0119(13) 0.0138(11) 0.0130(11) 0.0038(10) 0.0035(9) 0.0040(11)
C2 0.0149(14) 0.0154(12) 0.0177(12) 0.0012(11) 0.0046(10) 0.0027(11)
C3 0.0145(15) 0.0238(13) 0.0172(13) 0.0039(11) 0.0075(11) 0.0055(12)
C4 0.0106(14) 0.0218(13) 0.0229(13) 0.0039(11) 0.0054(11) -0.0029(11)
C5 0.0152(14) 0.0158(12) 0.0179(12) 0.0023(11) 0.0028(10) -0.0016(11)
C6 0.0118(13) 0.0140(11) 0.0116(11) 0.0035(10) 0.0019(9) 0.0000(10)
C7 0.0130(14) 0.0117(11) 0.0133(12) 0.0014(10) 0.0004(10) 0.0013(10)
C8 0.0130(14) 0.0135(11) 0.0156(12) -0.0021(10) 0.0044(10) 0.0004(11)
C9 0.0160(15) 0.0147(12) 0.0171(12) -0.0027(11) 0.0059(10) 0.0027(11)

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 C9 1.958(3) . ?
Cu1 O1 1.8962(18) . ?
Cu1 O1 1.8962(18) 3_666 ?
Cu1 N1 2.008(2) . ?
Cu1 N1 2.008(2) 3_666 ?
O1 C1 1.312(3) . ?
N1 C7 1.296(3) . ?
N1 C8 1.472(3) . ?
C1 C6 1.415(3) . ?
C1 C2 1.418(4) . ?
C2 C3 1.374(4) . ?
C2 H2 0.93(3) . ?
C3 C4 1.400(4) . ?
C3 H3 0.94(3) . ?
C4 C5 1.373(4) . ?
C4 H4 0.91(3) . ?
C5 C6 1.411(4) . ?
C5 H5 0.94(3) . ?
C6 C7 1.439(4) . ?
C7 H7 0.95(3) . ?
C8 C9 1.507(4) . ?
C8 H8A 0.99(3) . ?
C8 H8B 0.97(3) . ?
C9 H9A 0.92(3) . ?
C9 H9B 0.98(3) . ?

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 Cu1 O1 180.0 . 3_666 ?
O1 Cu1 N1 91.30(8) . . ?
O1 Cu1 N1 88.70(8) 3_666 . ?
O1 Cu1 N1 88.70(8) . 3_666 ?
O1 Cu1 N1 91.30(8) 3_666 3_666 ?
N1 Cu1 N1 180.000(1) . 3_666 ?
C1 O1 Cu1 130.37(16) . . ?
C7 N1 C8 115.3(2) . . ?
C7 N1 Cu1 124.82(17) . . ?
C8 N1 Cu1 119.76(17) . . ?
O1 C1 C6 124.1(2) . . ?
O1 C1 C2 118.6(2) . . ?
C6 C1 C2 117.4(2) . . ?
C3 C2 C1 121.5(3) . . ?
C3 C2 H2 122.5(19) . . ?
C1 C2 H2 115.9(19) . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3 118.5(19) . . ?
C4 C3 H3 120.5(19) . . ?
C5 C4 C3 118.7(3) . . ?
C5 C4 H4 120.6(19) . . ?
C3 C4 H4 120.3(19) . . ?
C4 C5 C6 121.8(2) . . ?
C4 C5 H5 118.3(18) . . ?
C6 C5 H5 119.9(18) . . ?
C5 C6 C1 119.7(2) . . ?
C5 C6 C7 118.1(2) . . ?
C1 C6 C7 122.1(2) . . ?
N1 C7 C6 126.8(2) . . ?
N1 C7 H7 119.0(17) . . ?
C6 C7 H7 114.1(17) . . ?
N1 C8 C9 109.9(2) . . ?
N1 C8 H8A 109.9(17) . . ?
C9 C8 H8A 111.1(16) . . ?
N1 C8 H8B 105.8(16) . . ?
C9 C8 H8B 112.7(17) . . ?
H8A C8 H8B 107(2) . . ?
C8 C9 Br1 108.54(17) . . ?
C8 C9 H9A 113.2(18) . . ?
Br1 C9 H9A 104.2(18) . . ?
C8 C9 H9B 115.1(18) . . ?
Br1 C9 H9B 105.9(17) . . ?
H9A C9 H9B 109(2) . . ?

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
O1 Cu1 O1 C1 130(86) 3_666 . . . ?
N1 Cu1 O1 C1 6.9(2) . . . . ?
N1 Cu1 O1 C1 -173.1(2) 3_666 . . . ?
O1 Cu1 N1 C7 -7.1(2) . . . . ?
O1 Cu1 N1 C7 172.9(2) 3_666 . . . ?
N1 Cu1 N1 C7 -125(100) 3_666 . . . ?
O1 Cu1 N1 C8 177.09(17) . . . . ?
O1 Cu1 N1 C8 -2.91(17) 3_666 . . . ?
N1 Cu1 N1 C8 59(100) 3_666 . . . ?
Cu1 O1 C1 C6 -4.9(4) . . . . ?
Cu1 O1 C1 C2 176.33(18) . . . . ?
O1 C1 C2 C3 178.0(2) . . . . ?
C6 C1 C2 C3 -0.8(4) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C2 C3 C4 C5 0.8(4) . . . . ?
C3 C4 C5 C6 -1.2(4) . . . . ?
C4 C5 C6 C1 0.6(4) . . . . ?
C4 C5 C6 C7 -178.3(2) . . . . ?
O1 C1 C6 C5 -178.3(2) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
O1 C1 C6 C7 0.5(4) . . . . ?
C2 C1 C6 C7 179.3(2) . . . . ?
C8 N1 C7 C6 -178.2(2) . . . . ?
Cu1 N1 C7 C6 5.8(4) . . . . ?
C5 C6 C7 N1 177.6(2) . . . . ?
C1 C6 C7 N1 -1.3(4) . . . . ?
C7 N1 C8 C9 109.2(2) . . . . ?
Cu1 N1 C8 C9 -74.5(2) . . . . ?
N1 C8 C9 Br1 174.21(17) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.099
#===============================================================================
_database_code_depnum_ccdc_archive 'CCDC 1007051'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ni

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'Ni (H2 O)4 (C9 H9 N O) 2+, 2Br -'
_chemical_formula_sum            'C18 H26 Br2 N2 Ni O6'
_chemical_formula_weight         584.94

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   11.2099(2)
_cell_length_b                   7.3582(2)
_cell_length_c                   13.2536(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.857(2)
_cell_angle_gamma                90.00
_cell_volume                     1090.74(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3215
_cell_measurement_theta_min      3.9491
_cell_measurement_theta_max      76.3992

_exptl_crystal_description       pyramid
_exptl_crystal_colour            olive
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.781
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             588
_exptl_absorpt_coefficient_mu    5.898
_exptl_absorpt_correction_T_min  0.3202
_exptl_absorpt_correction_T_max  0.3202
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis PRO (Agilent, 2012)'

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  
'Agilent Technologies SuperNova Dual diffractometer with Atlas detector'
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measurement_method       'ω scan'
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5502
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.95
_diffrn_reflns_theta_max         76.60
_reflns_number_total             2268
_reflns_number_gt                2155
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'CrysAlis PRO (Agilent, 2012)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'X-Seed (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0565P)²+0.6450P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0034(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2268
_refine_ls_number_parameters     150
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0869
_refine_ls_wR_factor_gt          0.0855
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.63686(2) -0.02878(4) 0.346503(18) 0.02195(13) Uani 1 1 d . . .
Ni1 Ni 0.5000 0.5000 0.5000 0.01850(16) Uani 1 2 d S . .
O1 O 0.05109(13) 0.6999(2) 0.47938(14) 0.0255(4) Uani 1 1 d . . .
O1W O 0.44393(14) 0.2445(2) 0.44944(13) 0.0234(3) Uani 1 1 d D . .
H11 H 0.492(3) 0.179(4) 0.420(3) 0.048(10) Uiso 1 1 d D . .
H12 H 0.412(3) 0.171(5) 0.489(3) 0.058(12) Uiso 1 1 d D . .
O2W O 0.54826(15) 0.5479(3) 0.35291(13) 0.0240(4) Uani 1 1 d D . .
H21 H 0.577(5) 0.652(4) 0.341(4) 0.093(18) Uiso 1 1 d D . .
H22 H 0.497(3) 0.515(5) 0.306(2) 0.045(11) Uiso 1 1 d D . .
N1 N 0.32829(16) 0.5956(3) 0.46259(15) 0.0219(4) Uani 1 1 d . . .
C1 C 0.31314(19) 0.7475(3) 0.41687(17) 0.0215(5) Uani 1 1 d . . .
H1 H 0.3853 0.8021 0.3985 0.026 Uiso 1 1 calc R . .
C2 C 0.20580(18) 0.8536(3) 0.38733(17) 0.0206(4) Uani 1 1 d . . .
C3 C 0.2269(2) 1.0007(4) 0.3228(2) 0.0247(5) Uani 1 1 d . . .
H3 H 0.3063 1.0216 0.3047 0.030 Uiso 1 1 calc R . .
C4 C 0.1384(2) 1.1152(4) 0.28492(19) 0.0299(5) Uani 1 1 d . . .
H4 H 0.1562 1.2138 0.2422 0.036 Uiso 1 1 calc R . .
C5 C 0.0210(2) 1.0836(4) 0.31067(19) 0.0276(5) Uani 1 1 d . . .
H5 H -0.0421 1.1588 0.2835 0.033 Uiso 1 1 calc R . .
C6 C -0.0030(2) 0.9439(4) 0.37517(19) 0.0245(5) Uani 1 1 d . . .
H6 H -0.0828 0.9248 0.3930 0.029 Uiso 1 1 calc R . .
C7 C 0.08809(19) 0.8293(3) 0.41506(17) 0.0208(4) Uani 1 1 d . . .
C8 C 0.13872(19) 0.6169(4) 0.54836(18) 0.0235(5) Uani 1 1 d . . .
H8A H 0.0976 0.5440 0.5983 0.028 Uiso 1 1 calc R . .
H8B H 0.1850 0.7131 0.5856 0.028 Uiso 1 1 calc R . .
C9 C 0.2238(2) 0.4956(4) 0.4954(2) 0.0241(5) Uani 1 1 d . . .
H9A H 0.2516 0.3966 0.5418 0.029 Uiso 1 1 calc R . .
H9B H 0.1807 0.4395 0.4356 0.029 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.02078(17) 0.02235(19) 0.02284(18) -0.00084(8) 0.00239(10) 0.00212(8)
Ni1 0.0149(3) 0.0207(3) 0.0200(3) -0.0005(2) 0.0015(2) 0.0031(2)
O1 0.0150(7) 0.0243(9) 0.0373(9) 0.0043(8) 0.0026(6) -0.0001(6)
O1W 0.0230(8) 0.0207(8) 0.0268(8) -0.0030(7) 0.0040(6) 0.0022(7)
O2W 0.0223(8) 0.0278(9) 0.0221(8) -0.0016(7) 0.0029(6) 0.0006(7)
N1 0.0165(8) 0.0253(11) 0.0241(9) 0.0002(8) 0.0023(7) 0.0026(8)
C1 0.0171(9) 0.0261(12) 0.0214(10) 0.0012(9) 0.0022(8) 0.0015(9)
C2 0.0170(9) 0.0239(12) 0.0205(10) 0.0002(9) -0.0010(7) 0.0013(9)
C3 0.0209(12) 0.0328(13) 0.0204(12) 0.0022(10) 0.0024(9) 0.0021(10)
C4 0.0367(13) 0.0316(13) 0.0216(11) 0.0053(10) 0.0026(9) 0.0060(11)
C5 0.0296(12) 0.0311(13) 0.0214(11) -0.0030(10) -0.0032(9) 0.0125(10)
C6 0.0200(10) 0.0278(12) 0.0254(11) -0.0078(10) -0.0014(9) 0.0053(9)
C7 0.0192(10) 0.0201(11) 0.0227(10) -0.0044(9) -0.0009(8) -0.0011(8)
C8 0.0201(10) 0.0242(12) 0.0266(11) 0.0020(10) 0.0041(8) -0.0016(9)
C9 0.0186(11) 0.0231(11) 0.0305(13) 0.0000(10) 0.0023(9) 0.0026(9)

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 2.0778(18) . ?
Ni1 N1 2.0778(18) 3_666 ?
Ni1 O1W 2.0790(18) . ?
Ni1 O1W 2.0790(18) 3_666 ?
Ni1 O2W 2.0879(18) 3_666 ?
Ni1 O2W 2.0879(18) . ?
O1 C7 1.361(3) . ?
O1 C8 1.433(3) . ?
O1W H11 0.840(10) . ?
O1W H12 0.849(10) . ?
O2W H21 0.849(10) . ?
O2W H22 0.848(10) . ?
N1 C1 1.277(3) . ?
N1 C9 1.473(3) . ?
C1 C2 1.465(3) . ?
C1 H1 0.9500 . ?
C2 C7 1.405(3) . ?
C2 C3 1.409(4) . ?
C3 C4 1.371(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.401(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.375(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.400(3) . ?
C6 H6 0.9500 . ?
C8 C9 1.513(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 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
N1 Ni1 N1 180.0 . 3_666 ?
N1 Ni1 O1W 88.51(7) . . ?
N1 Ni1 O1W 91.49(7) 3_666 . ?
N1 Ni1 O1W 91.49(7) . 3_666 ?
N1 Ni1 O1W 88.51(7) 3_666 3_666 ?
O1W Ni1 O1W 180.0 . 3_666 ?
N1 Ni1 O2W 89.19(7) . 3_666 ?
N1 Ni1 O2W 90.81(7) 3_666 3_666 ?
O1W Ni1 O2W 93.24(7) . 3_666 ?
O1W Ni1 O2W 86.76(7) 3_666 3_666 ?
N1 Ni1 O2W 90.81(7) . . ?
N1 Ni1 O2W 89.19(7) 3_666 . ?
O1W Ni1 O2W 86.76(7) . . ?
O1W Ni1 O2W 93.24(7) 3_666 . ?
O2W Ni1 O2W 180.0 3_666 . ?
C7 O1 C8 118.24(17) . . ?
Ni1 O1W H11 118(3) . . ?
Ni1 O1W H12 121(3) . . ?
H11 O1W H12 103(4) . . ?
Ni1 O2W H21 117(4) . . ?
Ni1 O2W H22 115(3) . . ?
H21 O2W H22 112(4) . . ?
C1 N1 C9 119.61(19) . . ?
C1 N1 Ni1 120.05(16) . . ?
C9 N1 Ni1 120.18(16) . . ?
N1 C1 C2 132.3(2) . . ?
N1 C1 H1 113.8 . . ?
C2 C1 H1 113.8 . . ?
C7 C2 C3 117.1(2) . . ?
C7 C2 C1 129.1(2) . . ?
C3 C2 C1 113.8(2) . . ?
C4 C3 C2 123.2(2) . . ?
C4 C3 H3 118.4 . . ?
C2 C3 H3 118.4 . . ?
C3 C4 C5 118.5(3) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 121.1(2) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
O1 C7 C6 114.4(2) . . ?
O1 C7 C2 125.7(2) . . ?
C6 C7 C2 119.9(2) . . ?
O1 C8 C9 112.4(2) . . ?
O1 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
O1 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
N1 C9 C8 112.4(2) . . ?
N1 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
N1 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1W Ni1 N1 C1 -136.13(19) . . . . ?
O1W Ni1 N1 C1 43.87(19) 3_666 . . . ?
O2W Ni1 N1 C1 130.60(19) 3_666 . . . ?
O2W Ni1 N1 C1 -49.40(19) . . . . ?
O1W Ni1 N1 C9 48.49(18) . . . . ?
O1W Ni1 N1 C9 -131.51(18) 3_666 . . . ?
O2W Ni1 N1 C9 -44.77(18) 3_666 . . . ?
O2W Ni1 N1 C9 135.23(18) . . . . ?
C9 N1 C1 C2 0.1(4) . . . . ?
Ni1 N1 C1 C2 -175.3(2) . . . . ?
N1 C1 C2 C7 10.7(4) . . . . ?
N1 C1 C2 C3 -170.0(3) . . . . ?
C7 C2 C3 C4 -1.8(4) . . . . ?
C1 C2 C3 C4 178.8(2) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C3 C4 C5 C6 2.0(4) . . . . ?
C4 C5 C6 C7 -1.0(4) . . . . ?
C8 O1 C7 C6 -159.9(2) . . . . ?
C8 O1 C7 C2 20.3(3) . . . . ?
C5 C6 C7 O1 178.7(2) . . . . ?
C5 C6 C7 C2 -1.5(4) . . . . ?
C3 C2 C7 O1 -177.4(2) . . . . ?
C1 C2 C7 O1 1.9(4) . . . . ?
C3 C2 C7 C6 2.8(3) . . . . ?
C1 C2 C7 C6 -177.9(2) . . . . ?
C7 O1 C8 C9 -69.4(3) . . . . ?
C1 N1 C9 C8 -46.7(3) . . . . ?
Ni1 N1 C9 C8 128.75(18) . . . . ?
O1 C8 C9 N1 88.5(2) . . . . ?

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
O1w H11 Br1 0.84(1) 2.48(1) 3.3134(16) 175(4) .
O1w H12 Br1 0.85(1) 2.51(2) 3.3141(17) 158(4) 3_656
O2w H21 Br1 0.85(1) 2.45(2) 3.2721(19) 165(5) 1_565
O2w H22 Br1 0.85(1) 2.46(1) 3.2973(18) 168(4) 2_655

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        76.60
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.677
_refine_diff_density_rms         0.091
#===============================================================================
_database_code_depnum_ccdc_archive 'CCDC 1007052'
