#------------------------------------------------------------------------------
#$Date: 2017-08-24 06:29:04 +0300 (Thu, 24 Aug 2017) $
#$Revision: 199915 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/40/7044018.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7044018
loop_
_publ_author_name
'Ghadwal, Rajendra S.'
'Ho, Nga Kim'
'Neumann, Beate'
'Stammler, Georg'
'Menezes da Silva, Vitor Hugo'
'Watanabe, Daniel'
'Braga, Ataualpa A. C.'
_publ_section_title
;
 Nickel-Catalysed Direct C2-Arylation of N-Heterocyclic Carbene
;
_journal_name_full               'Dalton Trans.'
_journal_paper_doi               10.1039/C7DT03099A
_journal_year                    2017
_chemical_formula_moiety         '2(C34 H43 N2), Br4 Ni [+ solvent]'
_chemical_formula_sum            'C68 H86 Br4 N4 Ni'
_chemical_formula_weight         1337.75
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-02-01
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_audit_update_record
;
2017-06-28 deposited with the CCDC.
2017-08-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.2084(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.2529(4)
_cell_length_b                   17.8637(4)
_cell_length_c                   18.7897(3)
_cell_measurement_reflns_used    17399
_cell_measurement_temperature    100.01(11)
_cell_measurement_theta_max      29.0840
_cell_measurement_theta_min      1.8770
_cell_volume                     7271.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0951
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.7909
_diffrn_measured_fraction_theta_max 0.9982
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -4.00  94.00   1.00   33.00    --   24.94  77.00 120.00   98
  2  ω      6.00  93.00   1.00   33.00    --   24.94  57.00  90.00   87
  3  ω    -44.00  54.00   1.00   33.00    --   24.94 -77.00   0.00   98
  4  ω    -44.00  54.00   1.00   33.00    --   24.94 -77.00-180.00   98
  5  ω     -4.00  94.00   1.00   33.00    --   24.94  77.00-150.00   98
  6  ω     -4.00  94.00   1.00   33.00    --   24.94  77.00  30.00   98
  7  ω    -20.00  65.00   1.00   33.00    --   24.94 -99.00 -60.00   85
  8  ω    -46.00  47.00   1.00   33.00    --   24.94 -38.00  60.00   93
  9  ω     -4.00  94.00   1.00   33.00    --   24.94  77.00 -60.00   98
 10  ω      7.00  85.00   1.00   33.00    --   24.94-133.00 145.75   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0189987000
_diffrn_orient_matrix_UB_12      0.0197862000
_diffrn_orient_matrix_UB_13      -0.0191705000
_diffrn_orient_matrix_UB_21      0.0132085000
_diffrn_orient_matrix_UB_22      0.0203056000
_diffrn_orient_matrix_UB_23      0.0322243000
_diffrn_orient_matrix_UB_31      0.0231582000
_diffrn_orient_matrix_UB_32      -0.0278070000
_diffrn_orient_matrix_UB_33      0.0098754000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            83727
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.11
_diffrn_reflns_theta_min         1.59
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.502
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.616
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_description       fragment
_exptl_crystal_F_000             2760
_exptl_crystal_size_max          0.296
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.019
_refine_diff_density_max         0.679
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     357
_refine_ls_number_reflns         10702
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0390
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0427P)²+10.0313P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.0963
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8207
_reflns_number_total             10702
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7dt03099a2.cif
_cod_data_source_block           compound_14
_cod_database_code               7044018
_chemical_oxdiff_formula         'C75 H94 Br4 N4 Ni'
_reflns_odcompleteness_completeness 79.09
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.78
_olex2_date_sample_data_collection 2017-01-31
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13), C22(H22), C25(H25)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7), C8(H8), C18(H18), C19(H19), C20(H20),
 C29(H29), C30(H30), C32(H32), C33(H33)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A,
 H27B,H27C), C34(H34A,H34B,H34C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.224
_oxdiff_exptl_absorpt_empirical_full_min 0.824
_shelx_shelxl_version_number     2016/4
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'
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
Br1 Br 0.79443(2) 0.64508(2) 0.42598(2) 0.02968(7) Uani 1 1 d . . .
Br2 Br 0.81590(2) 0.48951(2) 0.59386(2) 0.02468(6) Uani 1 1 d . . .
Ni1 Ni 0.750000 0.56219(2) 0.500000 0.01871(9) Uani 1 2 d S T P
N1 N 0.58685(7) 0.74634(10) 0.37626(9) 0.0155(3) Uani 1 1 d . . .
N2 N 0.51780(8) 0.66937(10) 0.39742(10) 0.0169(3) Uani 1 1 d . . .
C1 C 0.52614(9) 0.73874(11) 0.37370(11) 0.0149(4) Uani 1 1 d . . .
C2 C 0.61717(10) 0.68095(12) 0.40226(12) 0.0200(4) Uani 1 1 d . . .
H2 H 0.659290 0.671939 0.409447 0.024 Uiso 1 1 calc R . .
C3 C 0.57451(10) 0.63271(13) 0.41528(12) 0.0210(4) Uani 1 1 d . . .
H3 H 0.581546 0.584076 0.432876 0.025 Uiso 1 1 calc R . .
C4 C 0.61760(9) 0.80900(12) 0.35097(11) 0.0166(4) Uani 1 1 d . . .
C5 C 0.63262(10) 0.87161(12) 0.39599(12) 0.0202(4) Uani 1 1 d . . .
C6 C 0.66726(10) 0.92715(13) 0.37132(13) 0.0244(5) Uani 1 1 d . . .
H6 H 0.678442 0.970015 0.399309 0.029 Uiso 1 1 calc R . .
C7 C 0.68518(10) 0.91918(13) 0.30561(13) 0.0254(5) Uani 1 1 d . . .
H7 H 0.709227 0.956143 0.290999 0.030 Uiso 1 1 calc R . .
C8 C 0.66792(10) 0.85732(13) 0.26158(12) 0.0228(5) Uani 1 1 d . . .
H8 H 0.679110 0.854044 0.216926 0.027 Uiso 1 1 calc R . .
C9 C 0.63388(9) 0.79979(12) 0.28348(12) 0.0187(4) Uani 1 1 d . . .
C10 C 0.61486(11) 0.87998(14) 0.46884(12) 0.0260(5) Uani 1 1 d . . .
H10 H 0.590616 0.835827 0.475583 0.031 Uiso 1 1 calc R . .
C11 C 0.57421(16) 0.94874(17) 0.46938(18) 0.0462(7) Uani 1 1 d . . .
H11A H 0.596649 0.992965 0.462280 0.069 Uiso 1 1 calc GR . .
H11B H 0.562652 0.951824 0.515488 0.069 Uiso 1 1 calc GR . .
H11C H 0.537770 0.944675 0.430705 0.069 Uiso 1 1 calc GR . .
C12 C 0.67202(14) 0.8818(2) 0.53187(14) 0.0458(8) Uani 1 1 d . . .
H12A H 0.695618 0.836883 0.531183 0.069 Uiso 1 1 calc GR . .
H12B H 0.659550 0.885035 0.577422 0.069 Uiso 1 1 calc GR . .
H12C H 0.696825 0.924477 0.526617 0.069 Uiso 1 1 calc GR . .
C13 C 0.61814(10) 0.72991(13) 0.23649(12) 0.0219(4) Uani 1 1 d . . .
H13 H 0.591356 0.698534 0.258853 0.026 Uiso 1 1 calc R . .
C14 C 0.58279(10) 0.74817(15) 0.15857(13) 0.0271(5) Uani 1 1 d . . .
H14A H 0.545217 0.773848 0.160134 0.041 Uiso 1 1 calc GR . .
H14B H 0.573226 0.702594 0.131258 0.041 Uiso 1 1 calc GR . .
H14C H 0.607758 0.779523 0.135437 0.041 Uiso 1 1 calc GR . .
C15 C 0.67628(11) 0.68447(15) 0.23522(13) 0.0303(5) Uani 1 1 d . . .
H15A H 0.701320 0.711592 0.208652 0.045 Uiso 1 1 calc GR . .
H15B H 0.664664 0.637191 0.211824 0.045 Uiso 1 1 calc GR . .
H15C H 0.699280 0.676167 0.284397 0.045 Uiso 1 1 calc GR . .
C16 C 0.45869(9) 0.63233(12) 0.38793(12) 0.0184(4) Uani 1 1 d . . .
C17 C 0.43332(10) 0.62053(12) 0.44856(12) 0.0208(4) Uani 1 1 d . . .
C18 C 0.37699(11) 0.58200(15) 0.43600(14) 0.0303(5) Uani 1 1 d . . .
H18 H 0.358684 0.572712 0.474941 0.036 Uiso 1 1 calc R . .
C19 C 0.34817(12) 0.55757(16) 0.36687(15) 0.0366(6) Uani 1 1 d . . .
H19 H 0.310813 0.532100 0.359656 0.044 Uiso 1 1 calc R . .
C20 C 0.37476(12) 0.57090(16) 0.30843(14) 0.0344(6) Uani 1 1 d . . .
H20 H 0.354414 0.555017 0.262035 0.041 Uiso 1 1 calc R . .
C21 C 0.43108(11) 0.60741(13) 0.31719(13) 0.0240(5) Uani 1 1 d . . .
C22 C 0.46435(10) 0.64665(12) 0.52471(12) 0.0210(4) Uani 1 1 d . . .
H22 H 0.497493 0.681505 0.520960 0.025 Uiso 1 1 calc R . .
C23 C 0.41876(11) 0.68747(14) 0.56157(13) 0.0273(5) Uani 1 1 d . . .
H23A H 0.399809 0.728013 0.531001 0.041 Uiso 1 1 calc GR . .
H23B H 0.440481 0.706816 0.608006 0.041 Uiso 1 1 calc GR . .
H23C H 0.387518 0.653083 0.568729 0.041 Uiso 1 1 calc GR . .
C24 C 0.49292(12) 0.57988(14) 0.57203(14) 0.0305(5) Uani 1 1 d . . .
H24A H 0.460910 0.545561 0.576929 0.046 Uiso 1 1 calc GR . .
H24B H 0.513895 0.597428 0.619505 0.046 Uiso 1 1 calc GR . .
H24C H 0.521810 0.554912 0.549232 0.046 Uiso 1 1 calc GR . .
C25 C 0.46144(11) 0.61595(14) 0.25265(13) 0.0269(5) Uani 1 1 d . . .
H25 H 0.491994 0.656238 0.264374 0.032 Uiso 1 1 calc R . .
C26 C 0.41595(14) 0.63676(16) 0.18164(15) 0.0382(6) Uani 1 1 d . . .
H26A H 0.388123 0.595797 0.166101 0.057 Uiso 1 1 calc GR . .
H26B H 0.438171 0.647372 0.144615 0.057 Uiso 1 1 calc GR . .
H26C H 0.392925 0.680217 0.189507 0.057 Uiso 1 1 calc GR . .
C27 C 0.49567(15) 0.54405(18) 0.24231(16) 0.0419(7) Uani 1 1 d . . .
H27A H 0.525371 0.532583 0.286663 0.063 Uiso 1 1 calc GR . .
H27B H 0.516466 0.550765 0.203280 0.063 Uiso 1 1 calc GR . .
H27C H 0.466669 0.503627 0.230500 0.063 Uiso 1 1 calc GR . .
C28 C 0.47758(9) 0.79512(11) 0.35289(11) 0.0160(4) Uani 1 1 d . . .
C29 C 0.44139(10) 0.81238(13) 0.40234(12) 0.0233(5) Uani 1 1 d . . .
H29 H 0.449084 0.789020 0.447757 0.028 Uiso 1 1 calc R . .
C30 C 0.39427(11) 0.86393(14) 0.38407(13) 0.0277(5) Uani 1 1 d . . .
H30 H 0.370920 0.875414 0.417817 0.033 Uiso 1 1 calc R . .
C31 C 0.38092(11) 0.89912(14) 0.31625(13) 0.0259(5) Uani 1 1 d . . .
C32 C 0.41743(11) 0.88168(14) 0.26739(13) 0.0254(5) Uani 1 1 d . . .
H32 H 0.409405 0.904758 0.221824 0.031 Uiso 1 1 calc R . .
C33 C 0.46550(10) 0.83065(13) 0.28523(12) 0.0213(4) Uani 1 1 d . . .
H33 H 0.489603 0.820199 0.252021 0.026 Uiso 1 1 calc R . .
C34 C 0.32774(14) 0.95348(17) 0.29590(16) 0.0428(7) Uani 1 1 d . . .
H34A H 0.336328 0.989228 0.261379 0.064 Uiso 1 1 calc GR . .
H34B H 0.322449 0.979138 0.338943 0.064 Uiso 1 1 calc GR . .
H34C H 0.290662 0.926622 0.274439 0.064 Uiso 1 1 calc GR . .
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 1 0.0096
-1 0 -1 0.0096
-1 0 1 0.0572
1 0 -1 0.0572
-4 5 -2 0.1010
4 -5 2 0.1010
-3 -2 5 0.0636
5 -1 -2 0.0626
-5 1 2 0.0626
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
Br1 Ni1 Br1 103.60(2) . 2_656
Br1 Ni1 Br2 99.886(8) 2_656 .
Br1 Ni1 Br2 119.812(8) . .
Br1 Ni1 Br2 119.809(8) 2_656 2_656
Br1 Ni1 Br2 99.888(8) . 2_656
Br2 Ni1 Br2 114.53(2) 2_656 .
C1 N1 C2 109.39(17) . .
C1 N1 C4 127.69(17) . .
C2 N1 C4 122.74(16) . .
C1 N2 C3 109.10(17) . .
C1 N2 C16 124.85(17) . .
C3 N2 C16 124.25(18) . .
N1 C1 C28 127.82(18) . .
N2 C1 N1 107.12(17) . .
N2 C1 C28 125.00(18) . .
N1 C2 H2 126.3 . .
C3 C2 N1 107.35(18) . .
C3 C2 H2 126.3 . .
N2 C3 H3 126.5 . .
C2 C3 N2 107.04(19) . .
C2 C3 H3 126.5 . .
C5 C4 N1 119.10(18) . .
C5 C4 C9 124.39(19) . .
C9 C4 N1 116.38(19) . .
C4 C5 C6 116.2(2) . .
C4 C5 C10 123.37(19) . .
C6 C5 C10 120.4(2) . .
C5 C6 H6 119.5 . .
C7 C6 C5 120.9(2) . .
C7 C6 H6 119.5 . .
C6 C7 H7 119.4 . .
C8 C7 C6 121.2(2) . .
C8 C7 H7 119.4 . .
C7 C8 H8 119.7 . .
C7 C8 C9 120.6(2) . .
C9 C8 H8 119.7 . .
C4 C9 C13 123.12(19) . .
C8 C9 C4 116.7(2) . .
C8 C9 C13 120.12(19) . .
C5 C10 H10 107.6 . .
C5 C10 C11 111.2(2) . .
C5 C10 C12 111.1(2) . .
C11 C10 H10 107.6 . .
C11 C10 C12 111.6(2) . .
C12 C10 H10 107.6 . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11B 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C10 C12 H12A 109.5 . .
C10 C12 H12B 109.5 . .
C10 C12 H12C 109.5 . .
H12A C12 H12B 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C9 C13 H13 107.6 . .
C9 C13 C14 112.32(19) . .
C9 C13 C15 111.11(18) . .
C14 C13 H13 107.6 . .
C14 C13 C15 110.44(19) . .
C15 C13 H13 107.6 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14B 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C13 C15 H15A 109.5 . .
C13 C15 H15B 109.5 . .
C13 C15 H15C 109.5 . .
H15A C15 H15B 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C17 C16 N2 119.58(19) . .
C17 C16 C21 123.58(19) . .
C21 C16 N2 116.79(19) . .
C16 C17 C18 116.7(2) . .
C16 C17 C22 122.82(19) . .
C18 C17 C22 120.5(2) . .
C17 C18 H18 119.4 . .
C19 C18 C17 121.2(2) . .
C19 C18 H18 119.4 . .
C18 C19 H19 119.9 . .
C18 C19 C20 120.1(2) . .
C20 C19 H19 119.9 . .
C19 C20 H20 119.2 . .
C19 C20 C21 121.7(2) . .
C21 C20 H20 119.2 . .
C16 C21 C25 123.0(2) . .
C20 C21 C16 116.7(2) . .
C20 C21 C25 120.3(2) . .
C17 C22 H22 108.4 . .
C17 C22 C23 111.52(19) . .
C17 C22 C24 110.30(19) . .
C23 C22 H22 108.4 . .
C24 C22 H22 108.4 . .
C24 C22 C23 109.64(19) . .
C22 C23 H23A 109.5 . .
C22 C23 H23B 109.5 . .
C22 C23 H23C 109.5 . .
H23A C23 H23B 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C22 C24 H24A 109.5 . .
C22 C24 H24B 109.5 . .
C22 C24 H24C 109.5 . .
H24A C24 H24B 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
C21 C25 H25 107.8 . .
C21 C25 C26 113.2(2) . .
C21 C25 C27 110.0(2) . .
C26 C25 H25 107.8 . .
C26 C25 C27 110.1(2) . .
C27 C25 H25 107.8 . .
C25 C26 H26A 109.5 . .
C25 C26 H26B 109.5 . .
C25 C26 H26C 109.5 . .
H26A C26 H26B 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
C25 C27 H27A 109.5 . .
C25 C27 H27B 109.5 . .
C25 C27 H27C 109.5 . .
H27A C27 H27B 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
C29 C28 C1 118.51(19) . .
C33 C28 C1 122.33(19) . .
C33 C28 C29 119.14(19) . .
C28 C29 H29 119.9 . .
C30 C29 C28 120.2(2) . .
C30 C29 H29 119.9 . .
C29 C30 H30 119.3 . .
C29 C30 C31 121.4(2) . .
C31 C30 H30 119.3 . .
C30 C31 C32 117.9(2) . .
C30 C31 C34 120.9(2) . .
C32 C31 C34 121.2(2) . .
C31 C32 H32 119.3 . .
C33 C32 C31 121.4(2) . .
C33 C32 H32 119.3 . .
C28 C33 H33 120.1 . .
C32 C33 C28 119.9(2) . .
C32 C33 H33 120.1 . .
C31 C34 H34A 109.5 . .
C31 C34 H34B 109.5 . .
C31 C34 H34C 109.5 . .
H34A C34 H34B 109.5 . .
H34A C34 H34C 109.5 . .
H34B C34 H34C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 Ni1 2.3944(3) .
Br2 Ni1 2.4010(3) .
Ni1 Br1 2.3944(3) 2_656
Ni1 Br2 2.4010(3) 2_656
N1 C1 1.348(2) .
N1 C2 1.381(3) .
N1 C4 1.447(3) .
N2 C1 1.344(3) .
N2 C3 1.393(3) .
N2 C16 1.447(3) .
C1 C28 1.463(3) .
C2 H2 0.9300 .
C2 C3 1.345(3) .
C3 H3 0.9300 .
C4 C5 1.396(3) .
C4 C9 1.406(3) .
C5 C6 1.399(3) .
C5 C10 1.517(3) .
C6 H6 0.9300 .
C6 C7 1.389(3) .
C7 H7 0.9300 .
C7 C8 1.381(3) .
C8 H8 0.9300 .
C8 C9 1.394(3) .
C9 C13 1.523(3) .
C10 H10 0.9800 .
C10 C11 1.527(4) .
C10 C12 1.527(4) .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C13 H13 0.9800 .
C13 C14 1.531(3) .
C13 C15 1.532(3) .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
C16 C17 1.398(3) .
C16 C21 1.403(3) .
C17 C18 1.402(3) .
C17 C22 1.513(3) .
C18 H18 0.9300 .
C18 C19 1.381(3) .
C19 H19 0.9300 .
C19 C20 1.382(4) .
C20 H20 0.9300 .
C20 C21 1.389(3) .
C21 C25 1.525(3) .
C22 H22 0.9800 .
C22 C23 1.537(3) .
C22 C24 1.536(3) .
C23 H23A 0.9600 .
C23 H23B 0.9600 .
C23 H23C 0.9600 .
C24 H24A 0.9600 .
C24 H24B 0.9600 .
C24 H24C 0.9600 .
C25 H25 0.9800 .
C25 C26 1.525(4) .
C25 C27 1.528(4) .
C26 H26A 0.9600 .
C26 H26B 0.9600 .
C26 H26C 0.9600 .
C27 H27A 0.9600 .
C27 H27B 0.9600 .
C27 H27C 0.9600 .
C28 C29 1.396(3) .
C28 C33 1.391(3) .
C29 H29 0.9300 .
C29 C30 1.379(3) .
C30 H30 0.9300 .
C30 C31 1.391(3) .
C31 C32 1.393(3) .
C31 C34 1.511(3) .
C32 H32 0.9300 .
C32 C33 1.387(3) .
C33 H33 0.9300 .
C34 H34A 0.9600 .
C34 H34B 0.9600 .
C34 H34C 0.9600 .
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
N1 C1 C28 C29 -123.9(2)
N1 C1 C28 C33 57.5(3)
N1 C2 C3 N2 -0.4(2)
N1 C4 C5 C6 174.29(18)
N1 C4 C5 C10 -4.0(3)
N1 C4 C9 C8 -174.92(17)
N1 C4 C9 C13 2.7(3)
N2 C1 C28 C29 52.8(3)
N2 C1 C28 C33 -125.8(2)
N2 C16 C17 C18 -177.8(2)
N2 C16 C17 C22 1.5(3)
N2 C16 C21 C20 179.1(2)
N2 C16 C21 C25 1.8(3)
C1 N1 C2 C3 0.4(2)
C1 N1 C4 C5 82.1(3)
C1 N1 C4 C9 -102.0(2)
C1 N2 C3 C2 0.2(2)
C1 N2 C16 C17 -109.6(2)
C1 N2 C16 C21 72.9(3)
C1 C28 C29 C30 -178.5(2)
C1 C28 C33 C32 177.7(2)
C2 N1 C1 N2 -0.3(2)
C2 N1 C1 C28 176.9(2)
C2 N1 C4 C5 -103.4(2)
C2 N1 C4 C9 72.6(2)
C3 N2 C1 N1 0.0(2)
C3 N2 C1 C28 -177.26(19)
C3 N2 C16 C17 87.4(3)
C3 N2 C16 C21 -90.1(3)
C4 N1 C1 N2 174.87(19)
C4 N1 C1 C28 -7.9(3)
C4 N1 C2 C3 -175.03(19)
C4 C5 C6 C7 0.0(3)
C4 C5 C10 C11 -120.0(2)
C4 C5 C10 C12 115.1(3)
C4 C9 C13 C14 125.4(2)
C4 C9 C13 C15 -110.4(2)
C5 C4 C9 C8 0.8(3)
C5 C4 C9 C13 178.45(19)
C5 C6 C7 C8 1.9(3)
C6 C5 C10 C11 61.8(3)
C6 C5 C10 C12 -63.1(3)
C6 C7 C8 C9 -2.4(3)
C7 C8 C9 C4 1.1(3)
C7 C8 C9 C13 -176.62(19)
C8 C9 C13 C14 -57.1(3)
C8 C9 C13 C15 67.2(3)
C9 C4 C5 C6 -1.3(3)
C9 C4 C5 C10 -179.6(2)
C10 C5 C6 C7 178.3(2)
C16 N2 C1 N1 -165.17(18)
C16 N2 C1 C28 17.5(3)
C16 N2 C3 C2 165.5(2)
C16 C17 C18 C19 -0.4(4)
C16 C17 C22 C23 132.5(2)
C16 C17 C22 C24 -105.4(2)
C16 C21 C25 C26 -140.7(2)
C16 C21 C25 C27 95.7(3)
C17 C16 C21 C20 1.7(4)
C17 C16 C21 C25 -175.7(2)
C17 C18 C19 C20 0.0(4)
C18 C17 C22 C23 -48.2(3)
C18 C17 C22 C24 73.9(3)
C18 C19 C20 C21 1.3(5)
C19 C20 C21 C16 -2.1(4)
C19 C20 C21 C25 175.3(3)
C20 C21 C25 C26 42.1(3)
C20 C21 C25 C27 -81.5(3)
C21 C16 C17 C18 -0.5(3)
C21 C16 C17 C22 178.9(2)
C22 C17 C18 C19 -179.8(2)
C28 C29 C30 C31 0.9(4)
C29 C28 C33 C32 -0.9(3)
C29 C30 C31 C32 -1.1(4)
C29 C30 C31 C34 177.8(3)
C30 C31 C32 C33 0.3(4)
C31 C32 C33 C28 0.7(4)
C33 C28 C29 C30 0.1(3)
C34 C31 C32 C33 -178.6(3)
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.9990 -0.0004 0.9995 -0.0002 0.0454 0.0330
-0.9990 0.0004 -0.9995 0.0002 -0.0454 -0.0330
-0.9999 -0.0002 0.9997 -0.0382 0.0190 -0.0133
0.9999 0.0002 -0.9997 0.0382 -0.0190 0.0133
-3.9977 5.0002 -1.9978 0.0613 -0.0156 -0.2513
3.9977 -5.0002 1.9978 -0.0613 0.0156 0.2513
-3.0003 -2.0010 4.9979 -0.1924 0.0808 0.0355
4.9984 -0.9997 -2.0000 0.1135 -0.0187 0.1238
-4.9984 0.9997 2.0000 -0.1135 0.0187 -0.1238
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
1 -0.016 0.116 0.550 10.1 0.0
2 -0.016 0.384 0.050 10.1 0.0
3 0.016 0.616 0.950 10.1 0.0
4 0.016 0.884 0.450 10.1 0.0
5 0.250 0.750 -0.859 540.7 53.3
6 0.484 0.616 0.050 10.1 0.0
7 0.484 0.884 0.550 10.1 0.0
8 0.516 0.116 0.450 10.1 0.0
9 0.516 0.384 0.950 10.1 0.0
10 0.750 0.250 -0.359 540.7 53.3
