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

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1518430'
_audit_update_record             
;
2016-11-22 deposited with the CCDC.
2017-03-27 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         'C30 H44 Br2 N6 Ni2 O8'
_chemical_formula_sum            'C30 H44 Br2 N6 Ni2 O8'
_chemical_formula_weight         893.95

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.050(2)
_cell_length_b                   13.181(2)
_cell_length_c                   11.5502(19)
_cell_angle_alpha                90
_cell_angle_beta                 112.782(2)
_cell_angle_gamma                90
_cell_volume                     1831.7(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3218
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      24.37

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    3.264
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12917
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.692
_diffrn_reflns_theta_max         26.612
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3517
_reflns_number_gt                2678
_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       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELX97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep3 for Windows (Farrugia,1997)'
_computing_publication_material  'Wingx 1.80.05 (Farrugia, 1999)'

_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)+(0.0327P)²+0.2283P] 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         3517
_refine_ls_number_parameters     232
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0785
_refine_ls_wR_factor_gt          0.0725
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.031
_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
Ni1 Ni 0.91895(3) 0.95911(3) 0.87018(3) 0.02390(12) Uani 1 1 d . . . . .
Br1 Br 0.56242(3) 0.90874(3) 1.23546(4) 0.05285(14) Uani 1 1 d . . . . .
N1 N 0.7559(2) 0.93046(17) 0.7976(2) 0.0252(6) Uani 1 1 d . . . . .
O1W O 0.89911(19) 1.11340(15) 0.8198(2) 0.0334(5) Uani 1 1 d D . . . .
H11 H 0.917(3) 1.144(2) 0.766(2) 0.050 Uiso 1 1 d D U . . .
H12 H 0.937(2) 1.144(2) 0.8874(16) 0.050 Uiso 1 1 d D U . . .
O1 O 0.91510(16) 1.00279(14) 1.03517(18) 0.0248(5) Uani 1 1 d . . . . .
O2 O 0.90408(18) 0.89992(16) 0.6928(2) 0.0310(5) Uani 1 1 d . . . . .
H22 H 0.951(3) 0.848(3) 0.727(3) 0.047 Uiso 1 1 d . U . . .
O3 O 0.96365(17) 0.81349(15) 0.94609(18) 0.0311(5) Uani 1 1 d . . . . .
O4 O 1.0244(2) 0.74628(16) 0.8078(2) 0.0428(6) Uani 1 1 d . . . . .
C1 C 0.8375(2) 0.9765(2) 1.0764(3) 0.0245(7) Uani 1 1 d . . . . .
C2 C 0.8586(3) 0.9857(2) 1.2051(3) 0.0315(7) Uani 1 1 d . . . . .
H2 H 0.9289 1.0058 1.2603 0.038 Uiso 1 1 calc R U . . .
C3 C 0.7780(3) 0.9658(2) 1.2519(3) 0.0371(8) Uani 1 1 d . . . . .
H3 H 0.7938 0.9734 1.3371 0.045 Uiso 1 1 calc R U . . .
C4 C 0.6741(3) 0.9348(2) 1.1714(3) 0.0340(8) Uani 1 1 d . . . . .
C5 C 0.6507(3) 0.9214(2) 1.0465(3) 0.0345(8) Uani 1 1 d . . . . .
H5 H 0.5803 0.8992 0.9939 0.041 Uiso 1 1 calc R U . . .
C6 C 0.7311(3) 0.9406(2) 0.9956(3) 0.0266(7) Uani 1 1 d . . . . .
C7 C 0.6953(3) 0.9236(2) 0.8615(3) 0.0304(7) Uani 1 1 d . . . . .
H7 H 0.6212 0.9060 0.8180 0.036 Uiso 1 1 calc R U . . .
C8 C 0.7080(3) 0.9129(2) 0.6599(3) 0.0291(7) Uani 1 1 d . . . . .
C9 C 0.7966(3) 0.8528(3) 0.6340(3) 0.0391(8) Uani 1 1 d . . . . .
H9A H 0.7997 0.7843 0.6658 0.047 Uiso 1 1 calc R U . . .
H9B H 0.7771 0.8488 0.5441 0.047 Uiso 1 1 calc R U . . .
C10 C 0.6906(3) 1.0162(3) 0.5952(3) 0.0485(10) Uani 1 1 d . . . . .
H10A H 0.6400 1.0557 0.6189 0.073 Uiso 1 1 calc R U . . .
H10B H 0.6603 1.0069 0.5058 0.073 Uiso 1 1 calc R U . . .
H10C H 0.7605 1.0509 0.6204 0.073 Uiso 1 1 calc R U . . .
C11 C 0.5999(3) 0.8537(3) 0.6099(3) 0.0467(9) Uani 1 1 d . . . . .
H11A H 0.6086 0.7918 0.6566 0.070 Uiso 1 1 calc R U . . .
H11B H 0.5809 0.8381 0.5229 0.070 Uiso 1 1 calc R U . . .
H11C H 0.5419 0.8936 0.6187 0.070 Uiso 1 1 calc R U . . .
C12 C 1.0118(3) 0.7445(2) 0.9095(3) 0.0320(8) Uani 1 1 d . . . . .
C13 C 1.0575(3) 0.6557(3) 0.9966(3) 0.0542(11) Uani 1 1 d . . . . .
H13A H 1.0773 0.6023 0.9525 0.081 Uiso 1 1 calc R U . . .
H13B H 1.0022 0.6315 1.0255 0.081 Uiso 1 1 calc R U . . .
H13C H 1.1223 0.6767 1.0671 0.081 Uiso 1 1 calc R U . . .
C15 C 0.3163(4) 0.7899(3) 0.9335(5) 0.0886(17) Uani 1 1 d . U . . .
H15A H 0.3244 0.8547 0.9740 0.133 Uiso 1 1 calc R U . . .
H15B H 0.3544 0.7392 0.9947 0.133 Uiso 1 1 calc R U . . .
H15C H 0.2388 0.7729 0.8946 0.133 Uiso 1 1 calc R U . . .
C14 C 0.3627(5) 0.7943(4) 0.8401(6) 0.0880(17) Uani 1 1 d . U . . .
N3 N 0.3981(6) 0.7986(5) 0.7666(6) 0.148(2) Uani 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N1 1.998(2) . ?
Ni1 O1 2.0099(19) . ?
Ni1 O1 2.075(2) 3_777 ?
Ni1 O3 2.097(2) . ?
Ni1 O1W 2.103(2) . ?
Ni1 O2 2.130(2) . ?
Br1 C4 1.903(3) . ?
N1 C7 1.277(4) . ?
N1 C8 1.485(4) . ?
O1W H11 0.849(10) . ?
O1W H12 0.847(10) . ?
O1 C1 1.321(3) . ?
O1 Ni1 2.0745(19) 3_777 ?
O2 C9 1.440(4) . ?
O2 H22 0.90(3) . ?
O3 C12 1.267(4) . ?
O4 C12 1.248(4) . ?
C1 C2 1.408(4) . ?
C1 C6 1.422(4) . ?
C2 C3 1.381(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.366(4) . ?
C5 C6 1.410(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.452(4) . ?
C7 H7 0.9300 . ?
C8 C11 1.516(4) . ?
C8 C9 1.524(4) . ?
C8 C10 1.527(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.507(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 C14 1.429(7) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C14 N3 1.113(7) . ?

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 O1 92.20(9) . . ?
N1 Ni1 O1 172.62(9) . 3_777 ?
O1 Ni1 O1 80.52(8) . 3_777 ?
N1 Ni1 O3 94.64(9) . . ?
O1 Ni1 O3 88.33(8) . . ?
O1 Ni1 O3 86.37(8) 3_777 . ?
N1 Ni1 O1W 94.00(9) . . ?
O1 Ni1 O1W 86.53(8) . . ?
O1 Ni1 O1W 84.45(8) 3_777 . ?
O3 Ni1 O1W 170.10(9) . . ?
N1 Ni1 O2 80.89(9) . . ?
O1 Ni1 O2 172.14(8) . . ?
O1 Ni1 O2 106.45(8) 3_777 . ?
O3 Ni1 O2 88.51(8) . . ?
O1W Ni1 O2 97.62(9) . . ?
C7 N1 C8 120.6(3) . . ?
C7 N1 Ni1 124.7(2) . . ?
C8 N1 Ni1 114.66(18) . . ?
Ni1 O1W H11 128(2) . . ?
Ni1 O1W H12 104(2) . . ?
H11 O1W H12 103(2) . . ?
C1 O1 Ni1 124.82(18) . . ?
C1 O1 Ni1 131.50(19) . 3_777 ?
Ni1 O1 Ni1 99.48(8) . 3_777 ?
C9 O2 Ni1 108.71(17) . . ?
C9 O2 H22 105(2) . . ?
Ni1 O2 H22 94(2) . . ?
C12 O3 Ni1 127.7(2) . . ?
O1 C1 C2 119.7(3) . . ?
O1 C1 C6 122.7(3) . . ?
C2 C1 C6 117.6(3) . . ?
C3 C2 C1 122.0(3) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 120.7(3) . . ?
C5 C4 Br1 119.7(3) . . ?
C3 C4 Br1 119.6(2) . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 118.8(3) . . ?
C5 C6 C7 115.6(3) . . ?
C1 C6 C7 125.6(3) . . ?
N1 C7 C6 126.1(3) . . ?
N1 C7 H7 116.9 . . ?
C6 C7 H7 116.9 . . ?
N1 C8 C11 115.6(3) . . ?
N1 C8 C9 104.7(2) . . ?
C11 C8 C9 108.8(3) . . ?
N1 C8 C10 107.8(2) . . ?
C11 C8 C10 109.4(3) . . ?
C9 C8 C10 110.3(3) . . ?
O2 C9 C8 111.0(2) . . ?
O2 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
O2 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C12 O3 124.3(3) . . ?
O4 C12 C13 118.7(3) . . ?
O3 C12 C13 117.0(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C14 C15 179.2(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ni1 O1 C1 C2 161.5(2) . . . . ?
Ni1 O1 C1 C2 9.5(4) 3_777 . . . ?
Ni1 O1 C1 C6 -19.8(4) . . . . ?
Ni1 O1 C1 C6 -171.79(19) 3_777 . . . ?
O1 C1 C2 C3 175.6(3) . . . . ?
C6 C1 C2 C3 -3.2(4) . . . . ?
C1 C2 C3 C4 0.9(5) . . . . ?
C2 C3 C4 C5 1.4(5) . . . . ?
C2 C3 C4 Br1 -179.3(2) . . . . ?
C3 C4 C5 C6 -1.2(5) . . . . ?
Br1 C4 C5 C6 179.6(2) . . . . ?
C4 C5 C6 C1 -1.3(4) . . . . ?
C4 C5 C6 C7 -179.8(3) . . . . ?
O1 C1 C6 C5 -175.4(3) . . . . ?
C2 C1 C6 C5 3.4(4) . . . . ?
O1 C1 C6 C7 3.0(4) . . . . ?
C2 C1 C6 C7 -178.2(3) . . . . ?
C8 N1 C7 C6 -178.9(3) . . . . ?
Ni1 N1 C7 C6 3.7(4) . . . . ?
C5 C6 C7 N1 -175.7(3) . . . . ?
C1 C6 C7 N1 5.9(5) . . . . ?
C7 N1 C8 C11 -19.9(4) . . . . ?
Ni1 N1 C8 C11 157.8(2) . . . . ?
C7 N1 C8 C9 -139.7(3) . . . . ?
Ni1 N1 C8 C9 38.1(3) . . . . ?
C7 N1 C8 C10 102.8(3) . . . . ?
Ni1 N1 C8 C10 -79.5(3) . . . . ?
Ni1 O2 C9 C8 37.6(3) . . . . ?
N1 C8 C9 O2 -49.0(3) . . . . ?
C11 C8 C9 O2 -173.1(3) . . . . ?
C10 C8 C9 O2 66.8(3) . . . . ?
Ni1 O3 C12 O4 -12.5(5) . . . . ?
Ni1 O3 C12 C13 166.7(2) . . . . ?

_refine_diff_density_max         0.364
_refine_diff_density_min         -0.667
_refine_diff_density_rms         0.076

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1518431'
_audit_update_record             
;
2017-02-27 deposited with the CCDC.
2017-03-27 downloaded from the CCDC.
;
_audit_creation_date             2017-02-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_chemical_formula_moiety         'C26 H38 Br2 N4 Ni2 O6 S2, 2(C H4 O)'
_chemical_formula_sum            'C28 H46 Br2 N4 Ni2 O8 S2'
_chemical_formula_weight         908.03
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
Ni 0.35663 1.12491 12.83760 7.29200 4.44380 2.38000 3.87850 0.25650 12.17630
66.34210 1.03410005569
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2
5 -x,-y,-z
6 -x-1/2,y-1/2,z
7 x,-y-1/2,z-1/2
8 x-1/2,y,-z-1/2

_symmetry_Int_Tables_number      61
_cell_length_a                   10.556(3)
_cell_length_b                   18.209(6)
_cell_length_c                   20.193(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3881(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1987
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.68
_cell_measurement_theta_min      2.53
_exptl_absorpt_coefficient_mu    3.183
_exptl_absorpt_correction_T_max  0.752
_exptl_absorpt_correction_T_min  0.653
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_density_diffrn    1.5538
_exptl_crystal_description       prism
_exptl_crystal_F_000             1858.3397
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_diffrn_reflns_av_R_equivalents  0.0974
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21361
_diffrn_reflns_theta_full        23.67
_diffrn_reflns_theta_max         23.67
_diffrn_reflns_theta_min         2.02
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9943
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              0
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                2020
_reflns_number_total             2780
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.9984
_refine_diff_density_min         -0.7747
_refine_diff_density_rms         0.1256
_refine_ls_d_res_high            0.8995
_refine_ls_d_res_low             10.0967
_refine_ls_goodness_of_fit_ref   1.0105
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    33
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2780
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0423
_refine_ls_restrained_S_all      1.0105
_refine_ls_shift/su_max          0.0689
_refine_ls_shift/su_mean         0.0036
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0476P)²+3.1397P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.1053
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, H3 of O3, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, H2 of O2, H4 of O4
2.a Ternary CH refined with riding coordinates:
 N1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b), C9(H9a,H9b)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2a), C3(H3a), C5(H5)
2.d Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C11(H11a,H11b,H11c), C13(H13a,H13b,H13c), C14(H14a,H14b,
 H14c)
;
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_refinement_flags_posn
Ni Ni -0.13182(6) 0.53810(3) -0.00460(3) 0.0363(2) Uani 1.000000 .
Br1 Br 0.18963(6) 0.77595(3) 0.24139(3) 0.0667(3) Uani 1.000000 .
N1 N -0.1997(4) 0.6303(2) 0.0423(2) 0.0415(11) Uani 1.000000 .
N2 N -0.2183(4) 0.4620(3) 0.0543(3) 0.0538(13) Uani 1.000000 .
O1 O 0.0270(3) 0.54075(17) 0.05077(16) 0.0385(8) Uani 1.000000 .
O2 O -0.2921(4) 0.5587(2) -0.0611(2) 0.0621(13) Uani 1.000000 .
H2 H -0.308(7) 0.551(4) -0.095(3) 0.0931(19) Uiso 1.000000 R
O3 O -0.0323(4) 0.6140(2) -0.0683(2) 0.0512(11) Uani 1.000000 .
H3 H 0.032(5) 0.607(3) -0.060(3) 0.0615(13) Uiso 1.000000 R
S1 S -0.35008(17) 0.37808(12) 0.14515(11) 0.0992(8) Uani 1.000000 .
C1 C 0.0614(5) 0.5952(3) 0.0911(2) 0.0372(12) Uani 1.000000 .
C2 C 0.1882(5) 0.6097(3) 0.1030(3) 0.0484(14) Uani 1.000000 .
H2a H 0.2492(5) 0.5824(3) 0.0806(3) 0.0581(17) Uiso 1.000000 R
C3 C 0.2271(5) 0.6629(3) 0.1468(3) 0.0534(15) Uani 1.000000 .
H3a H 0.3129(5) 0.6709(3) 0.1543(3) 0.0641(18) Uiso 1.000000 R
C4 C 0.1381(6) 0.7037(3) 0.1790(3) 0.0464(14) Uani 1.000000 .
C5 C 0.0127(5) 0.6927(3) 0.1671(2) 0.0444(13) Uani 1.000000 .
H5 H -0.0466(5) 0.7218(3) 0.1887(2) 0.0532(16) Uiso 1.000000 R
C6 C -0.0285(5) 0.6389(3) 0.1233(2) 0.0418(13) Uani 1.000000 .
C7 C -0.1678(5) 0.6280(3) 0.1134(3) 0.0504(15) Uani 1.000000 .
H7a H -0.2141(5) 0.6662(3) 0.1366(3) 0.0604(18) Uiso 1.000000 R
H7b H -0.1930(5) 0.5810(3) 0.1317(3) 0.0604(18) Uiso 1.000000 R
C8 C -0.3319(5) 0.6488(3) 0.0226(3) 0.0517(15) Uani 1.000000 .
C9 C -0.3358(6) 0.6333(3) -0.0514(3) 0.0704(19) Uani 1.000000 .
H9a H -0.2814(6) 0.6674(3) -0.0749(3) 0.085(2) Uiso 1.000000 R
H9b H -0.4215(6) 0.6388(3) -0.0680(3) 0.085(2) Uiso 1.000000 R
C10 C -0.4265(5) 0.6033(4) 0.0593(4) 0.082(2) Uani 1.000000 .
H10a H -0.413(3) 0.5524(4) 0.0492(18) 0.123(3) Uiso 1.000000 GR
H10b H -0.416(3) 0.611(2) 0.1060(4) 0.123(3) Uiso 1.000000 GR
H10c H -0.5105(6) 0.6174(18) 0.0463(18) 0.123(3) Uiso 1.000000 GR
C11 C -0.3579(7) 0.7312(4) 0.0318(4) 0.091(2) Uani 1.000000 .
H11a H -0.354(5) 0.7432(6) 0.0780(5) 0.136(4) Uiso 1.000000 GR
H11b H -0.295(3) 0.7591(4) 0.008(2) 0.136(4) Uiso 1.000000 GR
H11c H -0.440(2) 0.7428(6) 0.015(2) 0.136(4) Uiso 1.000000 GR
C12 C -0.2734(5) 0.4278(3) 0.0917(3) 0.0505(15) Uani 1.000000 .
C13 C -0.0445(7) 0.6108(4) -0.1384(3) 0.088(2) Uani 1.000000 .
H13a H -0.038(5) 0.5607(5) -0.1528(4) 0.132(3) Uiso 1.000000 GR
H13b H -0.125(2) 0.630(3) -0.1512(3) 0.132(3) Uiso 1.000000 GR
H13c H 0.022(3) 0.639(2) -0.1585(3) 0.132(3) Uiso 1.000000 GR
O4 O -0.4091(6) 0.5124(3) -0.1671(3) 0.1106(19) Uani 1.000000 .
H4 H -0.488(8) 0.548(5) -0.168(4) 0.166(3) Uiso 1.000000 R
C14 C -0.3701(12) 0.4959(6) -0.2286(4) 0.157(4) Uani 1.000000 .
H14a H -0.368(8) 0.5398(9) -0.2550(13) 0.235(7) Uiso 1.000000 GR
H14b H -0.287(3) 0.475(4) -0.2267(6) 0.235(7) Uiso 1.000000 GR
H14c H -0.427(5) 0.461(4) -0.2481(16) 0.235(7) Uiso 1.000000 GR
H1 H -0.1521(4) 0.6678(2) 0.0259(2) 0.0499(13) Uiso 1.000000 R


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
Ni N1 2.058(4) . ?
Ni N2 2.041(5) . ?
Ni O1 2.038(3) 5_565 ?
Ni O1 2.016(3) . ?
Ni O2 2.075(4) . ?
Ni O3 2.160(4) . ?
Br1 C4 1.901(5) . ?
N1 C7 1.474(6) . ?
N1 C8 1.489(6) . ?
N1 H1 0.9100 . ?
N2 C12 1.139(6) . ?
O1 C1 1.334(5) . ?
O2 H2 0.72(7) . ?
O2 C9 1.448(7) . ?
O3 H3 0.71(6) . ?
O3 C13 1.423(7) . ?
S1 C12 1.625(7) . ?
C1 C2 1.385(7) . ?
C1 C6 1.399(7) . ?
C2 H2a 0.9300 . ?
C2 C3 1.374(7) . ?
C3 H3a 0.9300 . ?
C3 C4 1.362(7) . ?
C4 C5 1.360(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.390(7) . ?
C6 C7 1.497(7) . ?
C7 H7a 0.9700 . ?
C7 H7b 0.9700 . ?
C8 C9 1.520(8) . ?
C8 C10 1.495(8) . ?
C8 C11 1.537(8) . ?
C9 H9a 0.9700 . ?
C9 H9b 0.9700 . ?
C10 H10a 0.9600 . ?
C10 H10b 0.9600 . ?
C10 H10c 0.9600 . ?
C11 H11a 0.9600 . ?
C11 H11b 0.9600 . ?
C11 H11c 0.9600 . ?
C13 H13a 0.9600 . ?
C13 H13b 0.9600 . ?
C13 H13c 0.9600 . ?
O4 H4 1.06(8) . ?
O4 C14 1.343(9) . ?
C14 H14a 0.9600 . ?
C14 H14b 0.9600 . ?
C14 H14c 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Ni N1 97.45(18) . . ?
O1 Ni N1 90.84(14) . . ?
O1 Ni N1 167.12(14) 5_565 . ?
O1 Ni N2 91.80(16) 5_565 . ?
O1 Ni N2 93.74(16) . . ?
O2 Ni N1 79.71(15) . . ?
O2 Ni N2 94.47(19) . . ?
O2 Ni O1 168.21(15) . . ?
O2 Ni O1 108.59(14) . 5_565 ?
O3 Ni N1 85.49(16) . . ?
O3 Ni N2 176.77(16) . . ?
O3 Ni O1 85.09(14) . 5_565 ?
O3 Ni O1 84.86(14) . . ?
O3 Ni O2 87.36(17) . . ?
C7 N1 Ni 110.2(3) . . ?
C8 N1 Ni 112.8(3) . . ?
C8 N1 C7 118.8(4) . . ?
H1 N1 Ni 104.51(12) . . ?
H1 N1 C7 104.5(3) . . ?
H1 N1 C8 104.5(3) . . ?
C12 N2 Ni 170.5(5) . . ?
C1 O1 Ni 130.9(3) . 5_565 ?
C1 O1 Ni 125.7(3) . . ?
H2 O2 Ni 133(6) . . ?
C9 O2 Ni 110.8(3) . . ?
C9 O2 H2 104(6) . . ?
H3 O3 Ni 101(5) . . ?
C13 O3 Ni 121.5(4) . . ?
C13 O3 H3 109(5) . . ?
C2 C1 O1 120.7(4) . . ?
C6 C1 O1 121.4(4) . . ?
C6 C1 C2 117.9(5) . . ?
H2a C2 C1 118.9(3) . . ?
C3 C2 C1 122.3(5) . . ?
C3 C2 H2a 118.9(3) . . ?
H3a C3 C2 120.5(3) . . ?
C4 C3 C2 119.0(5) . . ?
C4 C3 H3a 120.5(3) . . ?
C3 C4 Br1 119.8(4) . . ?
C5 C4 Br1 119.8(4) . . ?
C5 C4 C3 120.4(5) . . ?
H5 C5 C4 119.3(3) . . ?
C6 C5 C4 121.4(5) . . ?
C6 C5 H5 119.3(3) . . ?
C5 C6 C1 118.9(5) . . ?
C7 C6 C1 122.0(5) . . ?
C7 C6 C5 119.1(5) . . ?
C6 C7 N1 110.5(4) . . ?
H7a C7 N1 109.5(3) . . ?
H7a C7 C6 109.5(3) . . ?
H7b C7 N1 109.5(3) . . ?
H7b C7 C6 109.5(3) . . ?
H7b C7 H7a 108.1 . . ?
C9 C8 N1 104.3(4) . . ?
C10 C8 N1 111.6(5) . . ?
C10 C8 C9 111.5(5) . . ?
C11 C8 N1 110.8(5) . . ?
C11 C8 C9 107.2(5) . . ?
C11 C8 C10 111.2(5) . . ?
C8 C9 O2 107.4(5) . . ?
H9a C9 O2 110.2(3) . . ?
H9a C9 C8 110.2(3) . . ?
H9b C9 O2 110.2(3) . . ?
H9b C9 C8 110.2(3) . . ?
H9b C9 H9a 108.5 . . ?
H10a C10 C8 109.5 . . ?
H10b C10 C8 109.5 . . ?
H10b C10 H10a 109.5 . . ?
H10c C10 C8 109.5 . . ?
H10c C10 H10a 109.5 . . ?
H10c C10 H10b 109.5 . . ?
H11a C11 C8 109.5 . . ?
H11b C11 C8 109.5 . . ?
H11b C11 H11a 109.5 . . ?
H11c C11 C8 109.5 . . ?
H11c C11 H11a 109.5 . . ?
H11c C11 H11b 109.5 . . ?
S1 C12 N2 179.1(5) . . ?
H13a C13 O3 109.5 . . ?
H13b C13 O3 109.5 . . ?
H13b C13 H13a 109.5 . . ?
H13c C13 O3 109.5 . . ?
H13c C13 H13a 109.5 . . ?
H13c C13 H13b 109.5 . . ?
C14 O4 H4 111(5) . . ?
H14a C14 O4 109.5 . . ?
H14b C14 O4 109.5 . . ?
H14b C14 H14a 109.5 . . ?
H14c C14 O4 109.5 . . ?
H14c C14 H14a 109.5 . . ?
H14c C14 H14b 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
