# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1504276'
_audit_update_record             
;
2017-01-21 deposited with the CCDC.
2017-02-13 downloaded from the CCDC.
;
#=======================================================================

# CHEMICAL DATA

_chemical_formula_moiety         'C27 H35 Br1 N2 Ni1'
_chemical_formula_sum            'C27 H35 Br1 N2 Ni1'
_chemical_formula_weight         526.2

#=======================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y+1/2,z+1/2

_cell_length_a                   18.1581(5)
_cell_length_b                   10.2051(4)
_cell_length_c                   14.2066(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.406(3)
_cell_angle_gamma                90
_cell_volume                     2624.78(18)
_cell_formula_units_Z            4

_cell_measurement_temperature    100

_cell_measurement_reflns_used    6701
_cell_measurement_theta_min      2.421
_cell_measurement_theta_max      31.691

_exptl_crystal_density_diffrn    1.3315
_exptl_crystal_F_000             1096
_exptl_absorpt_coefficient_mu    2.277
_exptl_crystal_description       plate
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.029

_exptl_crystal_colour            red
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.74222
_exptl_absorpt_correction_T_max  1.00000

#=======================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'microfocus source'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multi-layer optics'
_diffrn_measurement_device       'Agilent Technologies Opal detector'
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       ω-scans

_diffrn_reflns_number            37112
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         34.76
_diffrn_reflns_theta_full        34.06
_diffrn_measured_fraction_theta_max 0.94
_diffrn_measured_fraction_theta_full 0.98
_diffrn_reflns_av_R_equivalents  0.073
_diffrn_reflns_av_unetI/netI     0.0765
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20

#======================================================================

# REFINEMENT DATA

_reflns_number_total             10655
_reflns_number_gt                6189
_reflns_threshold_expression     I>3σ(I)

_refine_ls_structure_factor_coef F
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_gt          0.0383
_refine_ls_R_factor_all          0.0985
_refine_ls_wR_factor_ref         0.0463
_refine_ls_goodness_of_fit_ref   1.15
_refine_ls_goodness_of_fit_gt    1.25
_refine_ls_number_reflns         10655
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_number_constraints    140
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/(σ²(F)+0.0001F²)
_refine_ls_hydrogen_treatment    constr
_refine_ls_shift/su_max          0.0039
_refine_ls_shift/su_mean         0.0001
_refine_diff_density_max         0.61
_refine_diff_density_min         -0.53
_refine_ls_extinction_method     none

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
C 0.0033 0.0016 'International Tables Vol C tables 4.2.6.8 and 6.1.1.4' 2.31
20.843901 1.02 10.2075 1.5886 0.5687 0.865 51.651199 0.2156
H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.4'
0.493002 10.5109 0.322912 26.1257 0.140191 3.14236 0.04081 57.799702 0.003038
Br -0.2901 2.4595 'International Tables Vol C tables 4.2.6.8 and 6.1.1.4'
17.1789 2.1723 5.2358 16.579599 5.6377 0.2609 3.9851 41.4328 2.9557
N 0.0061 0.0033 'International Tables Vol C tables 4.2.6.8 and 6.1.1.4' 12.2126
0.0057 3.1322 9.8933 2.0125 28.997499 1.1663 0.5826 -11.529
Ni 0.3393 1.1124 'International Tables Vol C tables 4.2.6.8 and 6.1.1.4'
12.8376 3.8785 7.292 0.2565 4.4438 12.1763 2.38 66.342102 1.0341


#=======================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_adp_type
_atom_site_U_iso_or_equiv
_atom_site_site_symmetry_multiplicity
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.163894(11) 0.15372(2) 0.689978(17) Uani 0.01815(6) 4 1 d . . .
Ni1 Ni 0.212900(14) 0.35958(3) 0.73179(2) Uani 0.01339(8) 4 1 d . . .
N1 N 0.05971(9) 0.44673(19) 0.72395(13) Uani 0.0142(5) 4 1 d . . .
N2 N 0.11824(9) 0.53926(19) 0.61592(12) Uani 0.0124(5) 4 1 d . . .
C1 C 0.31361(12) 0.4618(3) 0.70931(19) Uani 0.0240(8) 4 1 d . . .
C2 C 0.27250(12) 0.5162(3) 0.78140(19) Uani 0.0261(8) 4 1 d . . .
C3 C 0.27371(12) 0.4260(3) 0.85863(19) Uani 0.0247(8) 4 1 d . . .
C4 C 0.30759(11) 0.3122(3) 0.82823(16) Uani 0.0189(7) 4 1 d . . .
C5 C 0.33357(11) 0.3345(3) 0.73497(16) Uani 0.0180(7) 4 1 d . . .
C6 C 0.38065(12) 0.2396(3) 0.68300(18) Uani 0.0267(8) 4 1 d . . .
C7 C 0.35853(16) 0.2447(4) 0.5769(2) Uani 0.0484(13) 4 1 d . . .
C8 C 0.37327(13) 0.0993(3) 0.7181(2) Uani 0.0336(9) 4 1 d . . .
C9 C 0.46259(12) 0.2844(3) 0.7002(2) Uani 0.0343(9) 4 1 d . . .
C10 C 0.49066(13) 0.2950(3) 0.8007(2) Uani 0.0372(10) 4 1 d . . .
C11 C 0.54359(17) 0.2204(4) 0.8410(2) Uani 0.0593(15) 4 1 d . . .
C12 C 0.07233(12) 0.6987(3) 0.89246(19) Uani 0.0305(9) 4 1 d . . .
C13 C 0.08312(11) 0.5727(3) 0.90815(16) Uani 0.0247(8) 4 1 d . . .
C14 C 0.02644(13) 0.4695(3) 0.88893(16) Uani 0.0227(7) 4 1 d . . .
C15 C 0.04416(12) 0.3754(2) 0.80940(15) Uani 0.0176(6) 4 1 d . . .
C16 C 0.12777(11) 0.4537(2) 0.68980(15) Uani 0.0133(6) 4 1 d . . .
C17 C 0.00941(11) 0.5257(2) 0.67280(16) Uani 0.0166(6) 4 1 d . . .
C18 C 0.04578(11) 0.5844(2) 0.60455(16) Uani 0.0153(6) 4 1 d . . .
C19 C 0.17635(10) 0.5829(2) 0.55932(15) Uani 0.0133(6) 4 1 d . . .
C20 C 0.20841(11) 0.7052(2) 0.57851(16) Uani 0.0157(6) 4 1 d . . .
C21 C 0.26537(11) 0.7437(3) 0.52404(17) Uani 0.0213(7) 4 1 d . . .
C22 C 0.28870(11) 0.6650(3) 0.45117(17) Uani 0.0201(7) 4 1 d . . .
C23 C 0.25318(11) 0.5458(2) 0.43311(16) Uani 0.0184(7) 4 1 d . . .
C24 C 0.19681(11) 0.5016(2) 0.48640(15) Uani 0.0149(6) 4 1 d . . .
C25 C 0.18224(13) 0.7964(2) 0.65232(18) Uani 0.0240(7) 4 1 d . . .
C26 C 0.35241(13) 0.7050(3) 0.39544(19) Uani 0.0291(8) 4 1 d . . .
C27 C 0.16094(12) 0.3704(2) 0.46709(16) Uani 0.0186(7) 4 1 d . . .
H1 H 0.325109 0.504201 0.654399 Uiso 0.0288 4 1 d . . .
H2 H 0.248802 0.597087 0.778695 Uiso 0.0313 4 1 d . . .
H3 H 0.255588 0.440151 0.917253 Uiso 0.0296 4 1 d . . .
H4 H 0.312757 0.234403 0.862187 Uiso 0.0227 4 1 d . . .
H7a H 0.39124 0.190217 0.544116 Uiso 0.0581 4 1 d . . .
H7b H 0.308767 0.213656 0.565122 Uiso 0.0581 4 1 d . . .
H7c H 0.361705 0.333338 0.555008 Uiso 0.0581 4 1 d . . .
H8a H 0.402204 0.041943 0.68207 Uiso 0.0404 4 1 d . . .
H8b H 0.390575 0.094571 0.783534 Uiso 0.0404 4 1 d . . .
H8c H 0.32237 0.073148 0.710616 Uiso 0.0404 4 1 d . . .
H9a H 0.494022 0.225624 0.66763 Uiso 0.0411 4 1 d . . .
H9b H 0.469105 0.367619 0.668878 Uiso 0.0411 4 1 d . . .
H10 H 0.469739 0.358056 0.83768 Uiso 0.0447 4 1 d . . .
H11a H 0.558351 0.230912 0.904667 Uiso 0.0712 4 1 d . . .
H11b H 0.566077 0.157274 0.805621 Uiso 0.0712 4 1 d . . .
H12a H 0.111184 0.757467 0.90352 Uiso 0.0366 4 1 d . . .
H12b H 0.025872 0.72891 0.870333 Uiso 0.0366 4 1 d . . .
H13 H 0.129657 0.546521 0.933088 Uiso 0.0297 4 1 d . . .
H14a H -0.021245 0.510085 0.873385 Uiso 0.0272 4 1 d . . .
H14b H 0.020706 0.419961 0.94618 Uiso 0.0272 4 1 d . . .
H15a H 0.086513 0.322021 0.830185 Uiso 0.0212 4 1 d . . .
H15b H 0.002707 0.316798 0.795415 Uiso 0.0212 4 1 d . . .
H17 H -0.040158 0.536457 0.683283 Uiso 0.0199 4 1 d . . .
H18 H 0.026253 0.643171 0.559202 Uiso 0.0183 4 1 d . . .
H21 H 0.288511 0.82383 0.536446 Uiso 0.0255 4 1 d . . .
H23 H 0.267525 0.493895 0.383894 Uiso 0.022 4 1 d . . .
H25a H 0.166076 0.746067 0.703988 Uiso 0.0288 4 1 d . . .
H25b H 0.222046 0.852889 0.674825 Uiso 0.0288 4 1 d . . .
H25c H 0.14193 0.848301 0.625218 Uiso 0.0288 4 1 d . . .
H26a H 0.363962 0.795577 0.407447 Uiso 0.035 4 1 d . . .
H26b H 0.394737 0.652078 0.414067 Uiso 0.035 4 1 d . . .
H26c H 0.339087 0.692886 0.329306 Uiso 0.035 4 1 d . . .
H27a H 0.171171 0.341052 0.405247 Uiso 0.0223 4 1 d . . .
H27b H 0.180241 0.308251 0.51332 Uiso 0.0223 4 1 d . . .
H27c H 0.10852 0.378352 0.470399 Uiso 0.0223 4 1 d . . .


#=======================================================================

# MOLECULAR GEOMETRY

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 Ni1 . . 2.3403(4) ?
Br1 N1 . . 3.590(2) ?
Ni1 C1 . . 2.150(2) ?
Ni1 C2 . . 2.026(3) ?
Ni1 C3 . . 2.149(3) ?
Ni1 C4 . . 2.169(2) ?
Ni1 C5 . . 2.2036(19) ?
Ni1 C16 . . 1.8774(18) ?
N1 C15 . . 1.462(3) ?
N1 C16 . . 1.364(2) ?
N1 C17 . . 1.382(3) ?
N2 C16 . . 1.367(2) ?
N2 C18 . . 1.391(2) ?
N2 C19 . . 1.444(3) ?
C1 C2 . . 1.425(4) ?
C1 C5 . . 1.390(4) ?
C1 H1 . . 0.9297 ?
C2 C3 . . 1.431(4) ?
C2 H2 . . 0.9303 ?
C3 C4 . . 1.398(4) ?
C3 H3 . . 0.9303 ?
C4 C5 . . 1.457(4) ?
C4 H4 . . 0.9302 ?
C5 C6 . . 1.521(4) ?
C6 C7 . . 1.531(4) ?
C6 C8 . . 1.525(4) ?
C6 C9 . . 1.557(3) ?
C7 H7a . . 0.9602 ?
C7 H7b . . 0.9595 ?
C7 H7c . . 0.9598 ?
C8 H8a . . 0.9599 ?
C8 H8b . . 0.9592 ?
C8 H8c . . 0.9606 ?
C9 C10 . . 1.483(4) ?
C9 H9a . . 0.9695 ?
C9 H9b . . 0.9702 ?
C10 C11 . . 1.321(4) ?
C10 H10 . . 0.9304 ?
C11 H11a . . 0.9296 ?
C11 H11b . . 0.9304 ?
C12 C13 . . 1.317(4) ?
C12 H12a . . 0.9304 ?
C12 H12b . . 0.9296 ?
C13 C14 . . 1.483(4) ?
C13 H13 . . 0.9306 ?
C14 C15 . . 1.536(4) ?
C14 H14a . . 0.9692 ?
C14 H14b . . 0.9703 ?
C15 H15a . . 0.9692 ?
C15 H15b . . 0.9705 ?
C17 C18 . . 1.354(4) ?
C17 H17 . . 0.9298 ?
C18 H18 . . 0.9309 ?
C19 C20 . . 1.396(3) ?
C19 C24 . . 1.400(4) ?
C20 C21 . . 1.396(3) ?
C20 C25 . . 1.506(4) ?
C21 C22 . . 1.400(4) ?
C21 H21 . . 0.9299 ?
C22 C23 . . 1.391(3) ?
C22 C26 . . 1.508(3) ?
C23 C24 . . 1.395(3) ?
C23 H23 . . 0.93 ?
C24 C27 . . 1.505(3) ?
C25 H25a . . 0.9601 ?
C25 H25b . . 0.9605 ?
C25 H25c . . 0.9592 ?
C26 H26a . . 0.9603 ?
C26 H26b . . 0.96 ?
C26 H26c . . 0.9594 ?
C27 H27a . . 0.9601 ?
C27 H27b . . 0.9599 ?
C27 H27c . . 0.9593 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Ni1 Br1 N1 . . . 54.01(3) ?
Br1 Ni1 C1 . . . 135.15(8) ?
Br1 Ni1 C2 . . . 168.22(7) ?
Br1 Ni1 C3 . . . 131.05(8) ?
Br1 Ni1 C4 . . . 103.16(8) ?
Br1 Ni1 C5 . . . 105.02(8) ?
Br1 Ni1 C16 . . . 95.22(6) ?
C1 Ni1 C2 . . . 39.77(10) ?
C1 Ni1 C3 . . . 65.39(10) ?
C1 Ni1 C4 . . . 63.90(10) ?
C1 Ni1 C5 . . . 37.21(11) ?
C1 Ni1 C16 . . . 113.15(9) ?
C2 Ni1 C3 . . . 39.94(11) ?
C2 Ni1 C4 . . . 65.16(11) ?
C2 Ni1 C5 . . . 65.20(10) ?
C2 Ni1 C16 . . . 96.40(9) ?
C3 Ni1 C4 . . . 37.78(11) ?
C3 Ni1 C5 . . . 64.74(10) ?
C3 Ni1 C16 . . . 117.54(9) ?
C4 Ni1 C5 . . . 38.93(10) ?
C4 Ni1 C16 . . . 155.22(9) ?
C5 Ni1 C16 . . . 149.21(10) ?
Br1 N1 C15 . . . 80.45(11) ?
Br1 N1 C16 . . . 59.64(11) ?
Br1 N1 C17 . . . 138.52(14) ?
C15 N1 C16 . . . 123.98(15) ?
C15 N1 C17 . . . 124.41(17) ?
C16 N1 C17 . . . 111.32(17) ?
C16 N2 C18 . . . 111.30(17) ?
C16 N2 C19 . . . 124.72(17) ?
C18 N2 C19 . . . 123.91(18) ?
Ni1 C1 C2 . . . 65.42(13) ?
Ni1 C1 C5 . . . 73.48(14) ?
Ni1 C1 H1 . . . 126.8 ?
C2 C1 C5 . . . 108.4(3) ?
C2 C1 H1 . . . 125.83 ?
C5 C1 H1 . . . 125.75 ?
Ni1 C2 C1 . . . 74.81(16) ?
Ni1 C2 C3 . . . 74.66(16) ?
Ni1 C2 H2 . . . 116.91 ?
C1 C2 C3 . . . 108.8(2) ?
C1 C2 H2 . . . 125.59 ?
C3 C2 H2 . . . 125.61 ?
Ni1 C3 C2 . . . 65.40(15) ?
Ni1 C3 C4 . . . 71.89(15) ?
Ni1 C3 H3 . . . 127.27 ?
C2 C3 C4 . . . 106.2(2) ?
C2 C3 H3 . . . 126.95 ?
C4 C3 H3 . . . 126.86 ?
Ni1 C4 C3 . . . 70.33(13) ?
Ni1 C4 C5 . . . 71.82(13) ?
Ni1 C4 H4 . . . 124.15 ?
C3 C4 C5 . . . 109.4(3) ?
C3 C4 H4 . . . 125.29 ?
C5 C4 H4 . . . 125.32 ?
Ni1 C5 C1 . . . 69.31(11) ?
Ni1 C5 C4 . . . 69.26(11) ?
Ni1 C5 C6 . . . 131.27(17) ?
C1 C5 C4 . . . 106.8(2) ?
C1 C5 C6 . . . 127.8(3) ?
C4 C5 C6 . . . 125.1(3) ?
C5 C6 C7 . . . 110.0(2) ?
C5 C6 C8 . . . 111.8(2) ?
C5 C6 C9 . . . 107.6(2) ?
C7 C6 C8 . . . 109.3(3) ?
C7 C6 C9 . . . 108.7(2) ?
C8 C6 C9 . . . 109.35(19) ?
C6 C7 H7a . . . 109.38 ?
C6 C7 H7b . . . 109.49 ?
C6 C7 H7c . . . 109.46 ?
H7a C7 H7b . . . 109.49 ?
H7a C7 H7c . . . 109.47 ?
H7b C7 H7c . . . 109.53 ?
C6 C8 H8a . . . 109.42 ?
C6 C8 H8b . . . 109.49 ?
C6 C8 H8c . . . 109.44 ?
H8a C8 H8b . . . 109.55 ?
H8a C8 H8c . . . 109.44 ?
H8b C8 H8c . . . 109.49 ?
C6 C9 C10 . . . 115.2(2) ?
C6 C9 H9a . . . 109.48 ?
C6 C9 H9b . . . 109.48 ?
C10 C9 H9a . . . 109.46 ?
C10 C9 H9b . . . 109.44 ?
H9a C9 H9b . . . 103.05 ?
C9 C10 C11 . . . 124.1(3) ?
C9 C10 H10 . . . 117.95 ?
C11 C10 H10 . . . 117.98 ?
C10 C11 H11a . . . 120.05 ?
C10 C11 H11b . . . 119.96 ?
H11a C11 H11b . . . 120 ?
C13 C12 H12a . . . 119.98 ?
C13 C12 H12b . . . 120.02 ?
H12a C12 H12b . . . 120 ?
C12 C13 C14 . . . 124.75(19) ?
C12 C13 H13 . . . 117.63 ?
C14 C13 H13 . . . 117.62 ?
C13 C14 C15 . . . 113.38(19) ?
C13 C14 H14a . . . 109.47 ?
C13 C14 H14b . . . 109.44 ?
C15 C14 H14a . . . 109.55 ?
C15 C14 H14b . . . 109.45 ?
H14a C14 H14b . . . 105.23 ?
N1 C15 C14 . . . 111.39(19) ?
N1 C15 H15a . . . 109.52 ?
N1 C15 H15b . . . 109.44 ?
C14 C15 H15a . . . 109.52 ?
C14 C15 H15b . . . 109.39 ?
H15a C15 H15b . . . 107.51 ?
Ni1 C16 N1 . . . 127.36(13) ?
Ni1 C16 N2 . . . 128.61(14) ?
N1 C16 N2 . . . 103.96(16) ?
N1 C17 C18 . . . 107.14(17) ?
N1 C17 H17 . . . 126.41 ?
C18 C17 H17 . . . 126.45 ?
N2 C18 C17 . . . 106.28(19) ?
N2 C18 H18 . . . 126.87 ?
C17 C18 H18 . . . 126.86 ?
N2 C19 C20 . . . 118.6(2) ?
N2 C19 C24 . . . 118.45(18) ?
C20 C19 C24 . . . 123.0(2) ?
C19 C20 C21 . . . 117.4(2) ?
C19 C20 C25 . . . 122.6(2) ?
C21 C20 C25 . . . 120.0(2) ?
C20 C21 C22 . . . 121.8(2) ?
C20 C21 H21 . . . 119.02 ?
C22 C21 H21 . . . 119.16 ?
C21 C22 C23 . . . 118.4(2) ?
C21 C22 C26 . . . 121.4(2) ?
C23 C22 C26 . . . 120.2(2) ?
C22 C23 C24 . . . 122.1(2) ?
C22 C23 H23 . . . 118.98 ?
C24 C23 H23 . . . 118.91 ?
C19 C24 C23 . . . 117.27(19) ?
C19 C24 C27 . . . 121.7(2) ?
C23 C24 C27 . . . 121.0(2) ?
C20 C25 H25a . . . 109.45 ?
C20 C25 H25b . . . 109.43 ?
C20 C25 H25c . . . 109.5 ?
H25a C25 H25b . . . 109.42 ?
H25a C25 H25c . . . 109.53 ?
H25b C25 H25c . . . 109.5 ?
C22 C26 H26a . . . 109.44 ?
C22 C26 H26b . . . 109.44 ?
C22 C26 H26c . . . 109.5 ?
H26a C26 H26b . . . 109.44 ?
H26a C26 H26c . . . 109.49 ?
H26b C26 H26c . . . 109.52 ?
C24 C27 H27a . . . 109.41 ?
C24 C27 H27b . . . 109.43 ?
C24 C27 H27c . . . 109.45 ?
H27a C27 H27b . . . 109.47 ?
H27a C27 H27c . . . 109.52 ?
H27b C27 H27c . . . 109.54 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Br1 Ni1 C16 N2 . . . . -112.60(17) ?

#=======================================================================

# EXTRA INFORMATION

_computing_molecular_graphics    
;
 Diamond - Crystal and Molecular Structure Visualization
 Crystal Impact - Dr. H. Putz & Dr. K. Brandenburg GbR, Germany
;
_computing_data_collection       
;
 CRYSALISPRO (Rigaku Oxford Diffraction, 2015)
;
_computing_structure_solution    
;
 SUPERFLIP, L. Palatinus, G. Chapuis, J. Appl. Cryst. 2007, 40, 786
;
_computing_structure_refinement  
;
 JANA2006, V. Petricek et al., Z. Kristallogr. 2014, 229, 345
;
_computing_publication_material  
;
 JANA2006, V. Petricek et al., Z. Kristallogr. 2014, 229, 345
;
_audit_creation_method           
;
 JANA2006, V. Petricek et al., Z. Kristallogr. 2014, 229, 345
;
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1504275'
_audit_update_record             
;
2017-01-21 deposited with the CCDC.
2017-02-13 downloaded from the CCDC.
;
#=======================================================================

# CHEMICAL DATA

_chemical_formula_moiety         'C27 H35 Br N2 Ni, C4 H10 O'
_chemical_formula_sum            'C31 H45 Br N2 Ni O'
_chemical_formula_weight         600.3

#=======================================================================

# CRYSTAL DATA

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   11.6986(16)
_cell_length_b                   12.2855(17)
_cell_length_c                   12.3121(17)
_cell_angle_alpha                60.8915(18)
_cell_angle_beta                 82.3538(18)
_cell_angle_gamma                80.5794(16)
_cell_volume                     1522.3(4)
_cell_formula_units_Z            2

_cell_measurement_temperature    112

_cell_measurement_reflns_used    7295
_cell_measurement_theta_max      30.33
_cell_measurement_theta_min      2.4

_exptl_crystal_density_diffrn    1.3097
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    1.974
_exptl_crystal_description       unspecified
_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_min          0.079

_exptl_crystal_colour            red
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1, Bruker AXS
Empirical absorption correction using spherical harmonics
;
_exptl_absorpt_correction_T_min  0.5994
_exptl_absorpt_correction_T_max  0.7461

#=======================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      112
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'TXS rotating anode'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_measurement_device       'Bruker AXS APEXII detector'
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       ω-scans

_diffrn_reflns_number            23733
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         30.99
_diffrn_reflns_theta_full        30.01
_diffrn_measured_fraction_theta_max 0.93
_diffrn_measured_fraction_theta_full 0.98
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

#======================================================================

# REFINEMENT DATA

_reflns_number_total             8972
_reflns_number_gt                6031
_reflns_threshold_expression     I>3σ(I)

_refine_ls_structure_factor_coef F
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_gt          0.0469
_refine_ls_R_factor_all          0.0729
_refine_ls_wR_factor_ref         0.0483
_refine_ls_goodness_of_fit_ref   1.77
_refine_ls_number_reflns         8972
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_number_constraints    180
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/(σ²(F)+0.0001F²)
_refine_ls_hydrogen_treatment    constr
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0000
_refine_diff_density_max         1.13
_refine_diff_density_min         -1.17
_refine_ls_extinction_method     none

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
C 0.0033 0.0016 'International Tables Vol C tables 4.2.6.8 and 6.1.1.4' 2.31
20.843901 1.02 10.2075 1.5886 0.5687 0.865 51.651199 0.2156
H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.4'
0.493002 10.5109 0.322912 26.1257 0.140191 3.14236 0.04081 57.799702 0.003038
Br -0.2901 2.4595 'International Tables Vol C tables 4.2.6.8 and 6.1.1.4'
17.1789 2.1723 5.2358 16.579599 5.6377 0.2609 3.9851 41.4328 2.9557
N 0.0061 0.0033 'International Tables Vol C tables 4.2.6.8 and 6.1.1.4' 12.2126
0.0057 3.1322 9.8933 2.0125 28.997499 1.1663 0.5826 -11.529
Ni 0.3393 1.1124 'International Tables Vol C tables 4.2.6.8 and 6.1.1.4'
12.8376 3.8785 7.292 0.2565 4.4438 12.1763 2.38 66.342102 1.0341
O 0.0106 0.0060 'International Tables Vol C tables 4.2.6.8 and 6.1.1.4' 3.0485
13.2771 2.2868 5.7011 1.5463 0.3239 0.867 32.908901 0.2508


#=======================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_adp_type
_atom_site_U_iso_or_equiv
_atom_site_site_symmetry_multiplicity
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.02020(2) 0.78438(3) -0.03479(3) Uani 0.02207(13) 2 1 d . . .
Ni1 Ni 0.09877(3) 0.70724(3) 0.13164(3) Uani 0.01203(14) 2 1 d . . .
N1 N 0.13194(17) 0.47349(19) 0.1181(2) Uani 0.0136(9) 2 1 d . . .
N2 N 0.29216(17) 0.55487(19) 0.07365(20) Uani 0.0130(9) 2 1 d . . .
C1 C 0.0712(2) 0.6670(3) 0.3261(2) Uani 0.0188(11) 2 1 d . . .
C2 C 0.1896(2) 0.6738(3) 0.2761(2) Uani 0.0181(11) 2 1 d . . .
C3 C 0.2028(2) 0.8004(3) 0.1834(3) Uani 0.0193(12) 2 1 d . . .
C4 C 0.0919(2) 0.8657(3) 0.1674(3) Uani 0.0182(11) 2 1 d . . .
C5 C 0.0096(2) 0.7837(2) 0.2582(2) Uani 0.0170(11) 2 1 d . . .
C6 C -0.1151(2) 0.8283(3) 0.2832(3) Uani 0.0221(12) 2 1 d . . .
C7 C -0.1726(2) 0.9244(3) 0.1624(3) Uani 0.0213(12) 2 1 d . . .
C8 C -0.1092(3) 0.8956(3) 0.3612(3) Uani 0.0304(14) 2 1 d . . .
C9 C -0.1864(2) 0.7188(3) 0.3602(3) Uani 0.0288(14) 2 1 d . . .
C10 C -0.1963(2) 0.6374(3) 0.3027(3) Uani 0.0259(14) 2 1 d . . .
C11 C -0.2075(2) 0.5145(3) 0.3680(3) Uani 0.0278(13) 2 1 d . . .
C12 C -0.2180(2) 0.4313(3) 0.3130(3) Uani 0.0232(12) 2 1 d . . .
C13 C -0.1202(2) 0.3221(3) 0.3465(3) Uani 0.0249(12) 2 1 d . . .
C14 C 0.0013(2) 0.3627(2) 0.3024(3) Uani 0.0204(11) 2 1 d . . .
C15 C 0.0122(2) 0.4459(2) 0.1623(2) Uani 0.0155(10) 2 1 d . . .
C16 C 0.1773(2) 0.5731(2) 0.1078(2) Uani 0.0136(10) 2 1 d . . .
C17 C 0.2159(2) 0.3951(2) 0.0902(2) Uani 0.0183(11) 2 1 d . . .
C18 C 0.3162(2) 0.4461(2) 0.0619(3) Uani 0.0174(11) 2 1 d . . .
C19 C 0.37636(20) 0.6391(2) 0.0478(2) Uani 0.0136(10) 2 1 d . . .
C20 C 0.4537(2) 0.6093(2) 0.1380(2) Uani 0.0158(11) 2 1 d . . .
C21 C 0.5325(2) 0.6944(2) 0.1113(3) Uani 0.0173(12) 2 1 d . . .
C22 C 0.5368(2) 0.8041(3) -0.0013(3) Uani 0.0183(12) 2 1 d . . .
C23 C 0.4606(2) 0.8283(2) -0.0907(3) Uani 0.0168(11) 2 1 d . . .
C24 C 0.3796(2) 0.7469(2) -0.0685(2) Uani 0.0145(11) 2 1 d . . .
C25 C 0.4565(2) 0.4872(3) 0.2587(3) Uani 0.0217(12) 2 1 d . . .
C26 C 0.6228(2) 0.8945(3) -0.0291(3) Uani 0.0265(14) 2 1 d . . .
C27 C 0.3000(2) 0.7722(2) -0.1668(3) Uani 0.0195(11) 2 1 d . . .
H1 H 0.041214 0.597031 0.392018 Uiso 0.0226 2 1 d . . .
H2 H 0.24815 0.606874 0.300067 Uiso 0.0218 2 1 d . . .
H3 H 0.271715 0.832675 0.14212 Uiso 0.0232 2 1 d . . .
H4 H 0.073147 0.948647 0.108045 Uiso 0.0218 2 1 d . . .
H7a H -0.129373 0.995446 0.119448 Uiso 0.0255 2 1 d . . .
H7b H -0.173631 0.886609 0.110288 Uiso 0.0255 2 1 d . . .
H7c H -0.250665 0.951138 0.182071 Uiso 0.0255 2 1 d . . .
H8a H -0.059492 0.960893 0.317282 Uiso 0.0365 2 1 d . . .
H8b H -0.18574 0.931335 0.374295 Uiso 0.0365 2 1 d . . .
H8c H -0.078884 0.836088 0.440198 Uiso 0.0365 2 1 d . . .
H9a H -0.155465 0.667374 0.441656 Uiso 0.0346 2 1 d . . .
H9b H -0.26345 0.749977 0.380493 Uiso 0.0346 2 1 d . . .
H10 H -0.194592 0.674699 0.216263 Uiso 0.031 2 1 d . . .
H11 H -0.208931 0.477829 0.454356 Uiso 0.0334 2 1 d . . .
H12a H -0.218971 0.481026 0.22309 Uiso 0.0279 2 1 d . . .
H12b H -0.292452 0.398436 0.340202 Uiso 0.0279 2 1 d . . .
H13a H -0.123721 0.268017 0.43598 Uiso 0.0299 2 1 d . . .
H13b H -0.134227 0.269008 0.312875 Uiso 0.0299 2 1 d . . .
H14a H 0.018677 0.406926 0.343353 Uiso 0.0244 2 1 d . . .
H14b H 0.057326 0.289835 0.325591 Uiso 0.0244 2 1 d . . .
H15a H -0.013689 0.405013 0.121109 Uiso 0.0186 2 1 d . . .
H15b H -0.038229 0.52377 0.139885 Uiso 0.0186 2 1 d . . .
H17 H 0.204808 0.321465 0.091026 Uiso 0.022 2 1 d . . .
H18 H 0.387669 0.414803 0.038848 Uiso 0.0209 2 1 d . . .
H21 H 0.583699 0.677011 0.170912 Uiso 0.0207 2 1 d . . .
H23 H 0.463988 0.900604 -0.167195 Uiso 0.0202 2 1 d . . .
H25a H 0.380518 0.459722 0.281063 Uiso 0.0261 2 1 d . . .
H25b H 0.510699 0.424778 0.248274 Uiso 0.0261 2 1 d . . .
H25c H 0.479898 0.499547 0.323364 Uiso 0.0261 2 1 d . . .
H26a H 0.624349 0.954412 -0.116125 Uiso 0.0318 2 1 d . . .
H26b H 0.600297 0.937485 0.019251 Uiso 0.0318 2 1 d . . .
H26c H 0.698586 0.849242 -0.008254 Uiso 0.0318 2 1 d . . .
H27a H 0.307619 0.700635 -0.180252 Uiso 0.0235 2 1 d . . .
H27b H 0.221194 0.788078 -0.139697 Uiso 0.0235 2 1 d . . .
H27c H 0.320432 0.844131 -0.243068 Uiso 0.0235 2 1 d . . .
O1 O 0.40557(18) 0.96190(19) 0.37677(19) Uani 0.0288(9) 2 1 d . . .
C28 C 0.4542(3) 0.7642(3) 0.3813(4) Uani 0.0420(18) 2 1 d . . .
C29 C 0.3601(3) 0.8528(3) 0.4000(3) Uani 0.0394(17) 2 1 d . . .
C30 C 0.3182(3) 1.0503(3) 0.3914(4) Uani 0.051(2) 2 1 d . . .
C31 C 0.3754(3) 1.1550(3) 0.3844(3) Uani 0.0450(18) 2 1 d . . .
H28a H 0.424308 0.686849 0.405028 Uiso 0.0504 2 1 d . . .
H28b H 0.481547 0.800652 0.29521 Uiso 0.0504 2 1 d . . .
H28c H 0.517198 0.748081 0.431705 Uiso 0.0504 2 1 d . . .
H29a H 0.302159 0.874139 0.345881 Uiso 0.0472 2 1 d . . .
H29b H 0.328411 0.814244 0.481548 Uiso 0.0472 2 1 d . . .
H30a H 0.278004 1.01096 0.468474 Uiso 0.0612 2 1 d . . .
H30b H 0.267405 1.082823 0.328009 Uiso 0.0612 2 1 d . . .
H31a H 0.317436 1.213566 0.396929 Uiso 0.0541 2 1 d . . .
H31b H 0.430071 1.121057 0.447894 Uiso 0.0541 2 1 d . . .
H31c H 0.415208 1.197084 0.304078 Uiso 0.0541 2 1 d . . .


#=======================================================================

# MOLECULAR GEOMETRY

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 Ni1 . . 2.3392(7) ?
Br1 N1 . . 3.601(2) ?
Ni1 C1 . . 2.185(3) ?
Ni1 C2 . . 2.027(3) ?
Ni1 C3 . . 2.138(4) ?
Ni1 C4 . . 2.183(4) ?
Ni1 C5 . . 2.252(3) ?
Ni1 C16 . . 1.884(3) ?
N1 C15 . . 1.465(3) ?
N1 C16 . . 1.356(4) ?
N1 C17 . . 1.391(4) ?
N2 C16 . . 1.370(3) ?
N2 C18 . . 1.393(4) ?
N2 C19 . . 1.439(4) ?
C1 C2 . . 1.437(3) ?
C1 C5 . . 1.389(3) ?
C1 H1 . . 0.93 ?
C2 C3 . . 1.432(4) ?
C2 H2 . . 0.9304 ?
C3 C4 . . 1.393(3) ?
C3 H3 . . 0.9301 ?
C4 C5 . . 1.458(3) ?
C4 H4 . . 0.9304 ?
C5 C6 . . 1.519(3) ?
C6 C7 . . 1.535(4) ?
C6 C8 . . 1.555(6) ?
C6 C9 . . 1.523(4) ?
C7 H7a . . 0.9599 ?
C7 H7b . . 0.9597 ?
C7 H7c . . 0.9597 ?
C8 H8a . . 0.9597 ?
C8 H8b . . 0.9603 ?
C8 H8c . . 0.9599 ?
C9 C10 . . 1.504(6) ?
C9 H9a . . 0.9702 ?
C9 H9b . . 0.9704 ?
C10 C11 . . 1.341(5) ?
C10 H10 . . 0.9305 ?
C11 C12 . . 1.502(6) ?
C11 H11 . . 0.9303 ?
C12 C13 . . 1.537(4) ?
C12 H12a . . 0.9705 ?
C12 H12b . . 0.9694 ?
C13 C14 . . 1.525(3) ?
C13 H13a . . 0.9704 ?
C13 H13b . . 0.9693 ?
C14 C15 . . 1.518(4) ?
C14 H14a . . 0.9596 ?
C14 H14b . . 0.96 ?
C15 H15a . . 0.9694 ?
C15 H15b . . 0.9701 ?
C17 C18 . . 1.345(3) ?
C17 H17 . . 0.9298 ?
C18 H18 . . 0.9302 ?
C19 C20 . . 1.396(4) ?
C19 C24 . . 1.401(3) ?
C20 C21 . . 1.397(4) ?
C20 C25 . . 1.513(3) ?
C21 C22 . . 1.388(4) ?
C21 H21 . . 0.9304 ?
C22 C23 . . 1.397(5) ?
C22 C26 . . 1.506(5) ?
C23 C24 . . 1.396(4) ?
C23 H23 . . 0.9302 ?
C24 C27 . . 1.506(4) ?
C25 H25a . . 0.9605 ?
C25 H25b . . 0.96 ?
C25 H25c . . 0.9596 ?
C26 H26a . . 0.9602 ?
C26 H26b . . 0.9598 ?
C26 H26c . . 0.9599 ?
C27 H27a . . 0.9594 ?
C27 H27b . . 0.9602 ?
C27 H27c . . 0.9602 ?
O1 C29 . . 1.408(5) ?
O1 C30 . . 1.426(5) ?
C28 C29 . . 1.495(5) ?
C28 H28a . . 0.9603 ?
C28 H28b . . 0.9598 ?
C28 H28c . . 0.9601 ?
C29 H29a . . 0.9296 ?
C29 H29b . . 0.9304 ?
C30 C31 . . 1.506(6) ?
C30 H30a . . 0.9299 ?
C30 H30b . . 0.9296 ?
C31 H31a . . 0.9601 ?
C31 H31b . . 0.9605 ?
C31 H31c . . 0.9597 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Ni1 Br1 N1 . . . 53.88(5) ?
Br1 Ni1 C1 . . . 135.11(6) ?
Br1 Ni1 C2 . . . 168.30(10) ?
Br1 Ni1 C3 . . . 131.05(7) ?
Br1 Ni1 C4 . . . 103.58(8) ?
Br1 Ni1 C5 . . . 105.97(6) ?
Br1 Ni1 C16 . . . 95.33(8) ?
C1 Ni1 C2 . . . 39.67(9) ?
C1 Ni1 C3 . . . 65.35(12) ?
C1 Ni1 C4 . . . 63.36(12) ?
C1 Ni1 C5 . . . 36.45(9) ?
C1 Ni1 C16 . . . 114.62(11) ?
C2 Ni1 C3 . . . 40.11(12) ?
C2 Ni1 C4 . . . 64.84(13) ?
C2 Ni1 C5 . . . 64.22(10) ?
C2 Ni1 C16 . . . 96.14(12) ?
C3 Ni1 C4 . . . 37.59(10) ?
C3 Ni1 C5 . . . 63.96(11) ?
C3 Ni1 C16 . . . 115.84(11) ?
C4 Ni1 C5 . . . 38.37(9) ?
C4 Ni1 C16 . . . 153.22(10) ?
C5 Ni1 C16 . . . 150.54(8) ?
Br1 N1 C15 . . . 79.74(11) ?
Br1 N1 C16 . . . 59.43(11) ?
Br1 N1 C17 . . . 139.48(13) ?
C15 N1 C16 . . . 124.7(2) ?
C15 N1 C17 . . . 123.8(2) ?
C16 N1 C17 . . . 111.3(2) ?
C16 N2 C18 . . . 110.9(2) ?
C16 N2 C19 . . . 124.9(2) ?
C18 N2 C19 . . . 124.1(2) ?
Ni1 C1 C2 . . . 64.23(14) ?
Ni1 C1 C5 . . . 74.37(14) ?
Ni1 C1 H1 . . . 126.61 ?
C2 C1 C5 . . . 107.7(2) ?
C2 C1 H1 . . . 126.14 ?
C5 C1 H1 . . . 126.16 ?
Ni1 C2 C1 . . . 76.10(16) ?
Ni1 C2 C3 . . . 74.09(18) ?
Ni1 C2 H2 . . . 116.27 ?
C1 C2 C3 . . . 108.9(2) ?
C1 C2 H2 . . . 125.57 ?
C3 C2 H2 . . . 125.54 ?
Ni1 C3 C2 . . . 65.8(2) ?
Ni1 C3 C4 . . . 73.0(2) ?
Ni1 C3 H3 . . . 125.95 ?
C2 C3 C4 . . . 106.3(2) ?
C2 C3 H3 . . . 126.87 ?
C4 C3 H3 . . . 126.8 ?
Ni1 C4 C3 . . . 69.5(2) ?
Ni1 C4 C5 . . . 73.4(2) ?
Ni1 C4 H4 . . . 123.39 ?
C3 C4 C5 . . . 109.4(2) ?
C3 C4 H4 . . . 125.37 ?
C5 C4 H4 . . . 125.27 ?
Ni1 C5 C1 . . . 69.18(16) ?
Ni1 C5 C4 . . . 68.3(2) ?
Ni1 C5 C6 . . . 134.8(2) ?
C1 C5 C4 . . . 107.3(2) ?
C1 C5 C6 . . . 127.95(19) ?
C4 C5 C6 . . . 124.1(2) ?
C5 C6 C7 . . . 111.9(2) ?
C5 C6 C8 . . . 106.0(3) ?
C5 C6 C9 . . . 111.6(2) ?
C7 C6 C8 . . . 107.6(3) ?
C7 C6 C9 . . . 111.4(3) ?
C8 C6 C9 . . . 108.0(3) ?
C6 C7 H7a . . . 109.44 ?
C6 C7 H7b . . . 109.44 ?
C6 C7 H7c . . . 109.42 ?
H7a C7 H7b . . . 109.5 ?
H7a C7 H7c . . . 109.51 ?
H7b C7 H7c . . . 109.52 ?
C6 C8 H8a . . . 109.51 ?
C6 C8 H8b . . . 109.43 ?
C6 C8 H8c . . . 109.47 ?
H8a C8 H8b . . . 109.47 ?
H8a C8 H8c . . . 109.51 ?
H8b C8 H8c . . . 109.45 ?
C6 C9 C10 . . . 115.8(3) ?
C6 C9 H9a . . . 109.45 ?
C6 C9 H9b . . . 109.41 ?
C10 C9 H9a . . . 109.5 ?
C10 C9 H9b . . . 109.51 ?
H9a C9 H9b . . . 102.26 ?
C9 C10 C11 . . . 124.2(3) ?
C9 C10 H10 . . . 117.91 ?
C11 C10 H10 . . . 117.86 ?
C10 C11 C12 . . . 125.3(3) ?
C10 C11 H11 . . . 117.37 ?
C12 C11 H11 . . . 117.35 ?
C11 C12 C13 . . . 113.3(3) ?
C11 C12 H12a . . . 109.42 ?
C11 C12 H12b . . . 109.51 ?
C13 C12 H12a . . . 109.43 ?
C13 C12 H12b . . . 109.5 ?
H12a C12 H12b . . . 105.35 ?
C12 C13 C14 . . . 114.3(2) ?
C12 C13 H13a . . . 109.44 ?
C12 C13 H13b . . . 109.51 ?
C14 C13 H13a . . . 109.41 ?
C14 C13 H13b . . . 109.5 ?
H13a C13 H13b . . . 104.23 ?
C13 C14 C15 . . . 111.6(2) ?
C13 C14 H14a . . . 109.5 ?
C13 C14 H14b . . . 109.45 ?
C15 C14 H14a . . . 109.5 ?
C15 C14 H14b . . . 109.45 ?
H14a C14 H14b . . . 107.25 ?
N1 C15 C14 . . . 111.6(2) ?
N1 C15 H15a . . . 109.49 ?
N1 C15 H15b . . . 109.42 ?
C14 C15 H15a . . . 109.52 ?
C14 C15 H15b . . . 109.46 ?
H15a C15 H15b . . . 107.22 ?
Ni1 C16 N1 . . . 127.63(18) ?
Ni1 C16 N2 . . . 128.2(2) ?
N1 C16 N2 . . . 104.2(2) ?
N1 C17 C18 . . . 106.9(3) ?
N1 C17 H17 . . . 126.5 ?
C18 C17 H17 . . . 126.59 ?
N2 C18 C17 . . . 106.7(2) ?
N2 C18 H18 . . . 126.68 ?
C17 C18 H18 . . . 126.62 ?
N2 C19 C20 . . . 119.07(17) ?
N2 C19 C24 . . . 118.7(2) ?
C20 C19 C24 . . . 122.3(2) ?
C19 C20 C21 . . . 117.66(19) ?
C19 C20 C25 . . . 121.8(2) ?
C21 C20 C25 . . . 120.5(2) ?
C20 C21 C22 . . . 122.1(3) ?
C20 C21 H21 . . . 118.95 ?
C22 C21 H21 . . . 118.96 ?
C21 C22 C23 . . . 118.4(3) ?
C21 C22 C26 . . . 121.5(3) ?
C23 C22 C26 . . . 120.1(2) ?
C22 C23 C24 . . . 121.8(2) ?
C22 C23 H23 . . . 119.1 ?
C24 C23 H23 . . . 119.08 ?
C19 C24 C23 . . . 117.7(2) ?
C19 C24 C27 . . . 120.9(2) ?
C23 C24 C27 . . . 121.36(19) ?
C20 C25 H25a . . . 109.43 ?
C20 C25 H25b . . . 109.5 ?
C20 C25 H25c . . . 109.5 ?
H25a C25 H25b . . . 109.43 ?
H25a C25 H25c . . . 109.46 ?
H25b C25 H25c . . . 109.5 ?
C22 C26 H26a . . . 109.44 ?
C22 C26 H26b . . . 109.5 ?
C22 C26 H26c . . . 109.46 ?
H26a C26 H26b . . . 109.47 ?
H26a C26 H26c . . . 109.46 ?
H26b C26 H26c . . . 109.5 ?
C24 C27 H27a . . . 109.47 ?
C24 C27 H27b . . . 109.45 ?
C24 C27 H27c . . . 109.46 ?
H27a C27 H27b . . . 109.51 ?
H27a C27 H27c . . . 109.51 ?
H27b C27 H27c . . . 109.44 ?
C29 O1 C30 . . . 111.9(3) ?
C29 C28 H28a . . . 109.47 ?
C29 C28 H28b . . . 109.49 ?
C29 C28 H28c . . . 109.49 ?
H28a C28 H28b . . . 109.46 ?
H28a C28 H28c . . . 109.44 ?
H28b C28 H28c . . . 109.48 ?
O1 C29 C28 . . . 109.9(3) ?
O1 C29 H29a . . . 109.52 ?
O1 C29 H29b . . . 109.44 ?
C28 C29 H29a . . . 109.49 ?
C28 C29 H29b . . . 109.46 ?
H29a C29 H29b . . . 108.98 ?
O1 C30 C31 . . . 108.9(3) ?
O1 C30 H30a . . . 109.49 ?
O1 C30 H30b . . . 109.53 ?
C31 C30 H30a . . . 109.44 ?
C31 C30 H30b . . . 109.42 ?
H30a C30 H30b . . . 110.05 ?
C30 C31 H31a . . . 109.49 ?
C30 C31 H31b . . . 109.47 ?
C30 C31 H31c . . . 109.51 ?
H31a C31 H31b . . . 109.42 ?
H31a C31 H31c . . . 109.49 ?
H31b C31 H31c . . . 109.45 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Br1 Ni1 C16 N2 . . . . 114.5(2) ?

#=======================================================================

# EXTRA INFORMATION

_computing_molecular_graphics    
;
 Diamond - Crystal and Molecular Structure Visualization
 Crystal Impact - Dr. H. Putz & Dr. K. Brandenburg GbR, Germany
;
_computing_data_collection       
;
 APEX2, Bruker AXS, 2016
;
_computing_structure_solution    
;
 SUPERFLIP, L. Palatinus, G. Chapuis, J. Appl. Cryst. 2007, 40, 786
;
_computing_structure_refinement  
;
 JANA2006, V. Petricek et al., Z. Kristallogr. 2014, 229, 345
;
_computing_publication_material  
;
 JANA2006, V. Petricek et al., Z. Kristallogr. 2014, 229, 345
;
_audit_creation_method           
;
 JANA2006, V. Petricek et al., Z. Kristallogr. 2014, 229, 345
;
