# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_HTpyMe
_database_code_depnum_ccdc_archive 'CCDC 2172875'
loop_
_audit_author_name
_audit_author_address
'Shiro Hikichi'
;Kanagawa University
Japan
;
_audit_update_record             
;
2022-05-16 deposited with the CCDC.	2022-05-30 downloaded from the CCDC.
;
_audit_creation_date             2022-05-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H24 B N3'
_chemical_formula_sum            'C24 H24 B N3'
_chemical_formula_weight         365.27
_chemical_melting_point          ?
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'
B B 0.0090 0.0039 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.1227(4)
_cell_length_b                   9.2714(3)
_cell_length_c                   16.9147(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.238(3)
_cell_angle_gamma                90
_cell_volume                     2018.48(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    24739
_cell_measurement_temperature    90
_cell_measurement_theta_max      76.5110
_cell_measurement_theta_min      3.9440
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.542
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.106a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            33233
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.352
_diffrn_reflns_theta_min         3.915
_diffrn_ambient_temperature      90.00
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     27.00  53.00   0.50    0.05    --   46.56  77.00   0.00   52
  2  ω     24.00  53.00   0.50    0.05    --   46.56  77.00 -30.00   58
  3  ω     29.00  54.00   0.50    0.05    --   46.56  77.00 -60.00   50
  4  ω     24.00  58.00   0.50    0.05    --   46.56  77.00 -90.00   68
  5  ω     32.00  66.00   0.50    0.05    --   46.56  57.00 -90.00   68
  6  ω     24.00  50.00   0.50    0.05    --   46.56  77.00-120.00   52
  7  ω     33.00  88.00   0.50    0.05    --   46.56  57.00-180.00  110
  8  ω     34.00  70.00   0.50    0.05    --   46.56  57.00-150.00   72
  9  ω     38.00  67.00   0.50    0.05    --   46.56  57.00-120.00   58
 10  ω     35.00  60.00   0.50    0.05    --   46.56  37.00 -90.00   50
 11  ω     44.00  81.00   0.50    0.05    --   46.56  19.00 -90.00   74
 12  ω     37.00  63.00   0.50    0.05    --   46.56   6.00-177.00   52
 13  ω    -10.00  24.00   0.50    0.05    --  -46.56   6.00-177.00   68
 14  ω    -54.00 -29.00   0.50    0.11    -- -102.00 109.00-102.91   50
 15  ω   -108.00 -70.00   0.50    0.11    -- -102.00 109.00-102.91   76
 16  ω     82.00 107.00   0.50    0.11    --  104.62  77.00-180.00   50
 17  ω    118.00 144.00   0.50    0.11    --  104.62   6.00-177.00   52
 18  ω    -25.00  24.00   0.50    0.05    --   46.56 -19.00 -90.00   98
 19  ω    -24.00   1.00   0.50    0.05    --   46.56  -6.00   5.00   50
 20  ω     66.00 108.00   0.50    0.11    --  104.62 -77.00-120.00   84
 21  ω     33.00  75.00   0.50    0.11    --  104.62 -61.00 -60.00   84
 22  ω     37.00  62.00   0.50    0.11    --  104.62 -77.00-120.00   50
 23  ω     32.00  75.00   0.50    0.11    --  104.62 -61.00-120.00   86
 24  ω     48.00  75.00   0.50    0.11    --  104.62 -94.00-180.00   54
 25  ω     78.00 104.00   0.50    0.11    --  104.62 -94.00-180.00   52
 26  ω     36.00 103.00   0.50    0.11    --  104.62 -94.00-150.00  134
 27  ω     18.00  91.00   0.50    0.05    --   46.56-125.00-180.00  146
 28  ω   -112.00 -70.00   0.50    0.05    --  -46.56  -6.00   5.00   84
 29  ω   -104.00 -79.00   0.50    0.11    -- -102.00 -77.00 -60.00   50
 30  ω   -105.00 -79.00   0.50    0.11    -- -102.00 -77.00 -90.00   52
 31  ω   -106.00 -81.00   0.50    0.11    -- -102.00 -77.00-112.01   50
 32  ω   -104.00 -79.00   0.50    0.11    -- -102.00 -77.00-150.00   50
 33  ω   -104.00 -79.00   0.50    0.11    -- -102.00 -77.00-180.00   50
 34  ω   -150.00-124.00   0.50    0.11    -- -102.00 -77.00-150.00   52
 35  ω   -169.00-143.00   0.50    0.11    -- -102.00 -77.00 -90.00   52
 36  ω   -104.00 -79.00   0.50    0.11    -- -102.00 -76.00-122.75   50
 37  ω   -104.00 -79.00   0.50    0.11    -- -102.00 -76.00 -82.12   50
 38  ω   -105.00 -80.00   0.50    0.11    -- -102.00 -77.00 -30.00   50
 39  ω   -105.00 -80.00   0.50    0.11    -- -102.00 -74.00 -29.97   50
 40  ω   -104.00 -79.00   0.50    0.11    -- -102.00 -76.00   2.90   50
 41  ω   -108.00 -83.00   0.50    0.11    -- -102.00 -77.00   0.00   50
 42  ω   -109.00 -82.00   0.50    0.11    -- -102.00 -71.00 -58.05   54
 43  ω   -107.00 -82.00   0.50    0.11    -- -102.00 -72.00-111.33   50
 44  ω   -174.00 -82.00   0.50    0.11    -- -102.00 -71.00-103.93  184
 45  ω   -173.00-147.00   0.50    0.11    -- -102.00 -76.00   2.90   52
 46  ω   -175.00-149.00   0.50    0.11    -- -102.00 -74.00 -29.97   52
 47  ω   -174.00-148.00   0.50    0.11    -- -102.00 -68.00 -24.63   52
 48  ω   -162.00-136.00   0.50    0.11    -- -102.00 -71.00 -58.05   52
 49  ω   -109.00 -84.00   0.50    0.11    -- -102.00 -66.00 -32.89   50
 50  ω   -108.00 -83.00   0.50    0.11    -- -102.00 -68.00 -24.63   50
 51  ω   -109.00 -84.00   0.50    0.11    -- -102.00 -64.00 -57.37   50
 52  ω   -114.00 -85.00   0.50    0.11    -- -102.00 -64.00 -91.02   58
 53  ω   -110.00 -85.00   0.50    0.11    -- -102.00 -63.00 -84.78   50
 54  ω   -108.00 -83.00   0.50    0.11    -- -102.00 -68.00-147.89   50
 55  ω   -108.00 -83.00   0.50    0.11    -- -102.00 -67.00-169.30   50
 56  ω   -110.00 -85.00   0.50    0.11    -- -102.00 -61.00-150.00   50
 57  ω   -164.00 -87.00   0.50    0.11    -- -102.00 -56.00-169.60  154
 58  ω   -175.00 -84.00   0.50    0.11    -- -102.00 -64.00-120.68  182
 59  ω   -151.00 -90.00   0.50    0.11    -- -102.00 -61.00 -90.00  122
 60  ω   -112.00 -87.00   0.50    0.11    -- -102.00 -61.00 -30.00   50
 61  ω   -112.00 -87.00   0.50    0.11    -- -102.00 -57.00 -14.03   50
 62  ω   -113.00 -88.00   0.50    0.11    -- -102.00 -54.00 -30.25   50
 63  ω   -174.00 -88.00   0.50    0.11    -- -102.00 -48.00 -20.71  172
 64  ω   -173.00 -88.00   0.50    0.11    -- -102.00 -53.00 -34.41  170
 65  ω   -132.00 -94.00   0.50    0.11    -- -102.00 -47.00 -66.79   76
 66  ω   -150.00-125.00   0.50    0.11    -- -102.00  -6.00   5.00   50
 67  ω    -88.00 -35.00   0.50    0.05    --  -46.56 -43.00-119.77  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1149312000
_diffrn_orient_matrix_UB_12      -0.0006459000
_diffrn_orient_matrix_UB_13      -0.0081327000
_diffrn_orient_matrix_UB_21      0.0334011000
_diffrn_orient_matrix_UB_22      0.0127392000
_diffrn_orient_matrix_UB_23      0.0923326000
_diffrn_orient_matrix_UB_31      0.0019217000
_diffrn_orient_matrix_UB_32      -0.1654389000
_diffrn_orient_matrix_UB_33      0.0072542000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3795
_reflns_number_total             4095
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.106a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.106a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.106a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         4095
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0453P)²+0.7212P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.0976
_refine_special_details          ?
_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 Aromatic/amide H refined with riding coordinates:
 C9(H9), C3(H3), C21(H21), C2(H2), C15(H15), C16(H16), C17(H17), C11(H11),
 C25(H25), C24(H24), C23(H23), C22(H22), C4(H4), C10(H10)
2.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
N13 N 0.54966(7) 1.06418(10) 0.26417(5) 0.02013(19) Uani 1 1 d . . . . .
N6 N 0.60500(7) 0.83976(10) 0.18951(5) 0.0212(2) Uani 1 1 d . . . . .
N19 N 0.72557(7) 0.82816(10) 0.44331(5) 0.0239(2) Uani 1 1 d . . . . .
C8 C 0.55797(8) 0.99149(12) 0.33475(6) 0.0197(2) Uani 1 1 d . . . . .
C14 C 0.63339(8) 0.75927(11) 0.41767(6) 0.0199(2) Uani 1 1 d . . . . .
C9 C 0.55679(8) 1.07603(12) 0.40314(7) 0.0239(2) Uani 1 1 d . . . . .
H9 H 0.563528 1.032156 0.453333 0.029 Uiso 1 1 calc R U . . .
C20 C 0.44282(8) 0.75685(11) 0.32051(6) 0.0202(2) Uani 1 1 d . . . . .
C3 C 0.70055(8) 0.57507(13) 0.19213(7) 0.0252(2) Uani 1 1 d . . . . .
H3 H 0.731152 0.484494 0.192717 0.030 Uiso 1 1 calc R U . . .
C21 C 0.40171(9) 0.65205(13) 0.26404(7) 0.0263(2) Uani 1 1 d . . . . .
H21 H 0.443257 0.615892 0.229934 0.032 Uiso 1 1 calc R U . . .
C2 C 0.66604(8) 0.62539(12) 0.25959(7) 0.0228(2) Uani 1 1 d . . . . .
H2 H 0.676423 0.570041 0.306333 0.027 Uiso 1 1 calc R U . . .
C15 C 0.60510(9) 0.64500(12) 0.46280(6) 0.0228(2) Uani 1 1 d . . . . .
H15 H 0.542969 0.596382 0.444583 0.027 Uiso 1 1 calc R U . . .
C16 C 0.66906(9) 0.60331(13) 0.53476(7) 0.0269(2) Uani 1 1 d . . . . .
H16 H 0.650005 0.527589 0.564893 0.032 Uiso 1 1 calc R U . . .
C17 C 0.76142(9) 0.67634(13) 0.56071(7) 0.0270(2) Uani 1 1 d . . . . .
H17 H 0.805201 0.651699 0.608928 0.032 Uiso 1 1 calc R U . . .
C1 C 0.61575(8) 0.75874(11) 0.25782(6) 0.0194(2) Uani 1 1 d . . . . .
C11 C 0.53649(9) 1.29123(12) 0.32213(7) 0.0272(3) Uani 1 1 d . . . . .
H11 H 0.527845 1.390650 0.317644 0.033 Uiso 1 1 calc R U . . .
C25 C 0.37527(9) 0.80742(13) 0.36953(7) 0.0262(2) Uani 1 1 d . . . . .
H25 H 0.398996 0.877971 0.407774 0.031 Uiso 1 1 calc R U . . .
C24 C 0.27436(9) 0.75601(14) 0.36302(8) 0.0308(3) Uani 1 1 d . . . . .
H24 H 0.232139 0.791855 0.396696 0.037 Uiso 1 1 calc R U . . .
C23 C 0.23684(9) 0.65134(14) 0.30632(8) 0.0317(3) Uani 1 1 d . . . . .
H23 H 0.169481 0.616476 0.301681 0.038 Uiso 1 1 calc R U . . .
C22 C 0.30060(9) 0.59932(14) 0.25672(8) 0.0331(3) Uani 1 1 d . . . . .
H22 H 0.276148 0.529131 0.218431 0.040 Uiso 1 1 calc R U . . .
C12 C 0.54034(8) 1.20874(12) 0.25496(7) 0.0232(2) Uani 1 1 d . . . . .
C4 C 0.68904(8) 0.66094(13) 0.12386(7) 0.0256(2) Uani 1 1 d . . . . .
H4 H 0.712116 0.629192 0.078243 0.031 Uiso 1 1 calc R U . . .
C5 C 0.64270(9) 0.79439(13) 0.12484(6) 0.0241(2) Uani 1 1 d . . . . .
C10 C 0.54573(9) 1.22386(13) 0.39680(7) 0.0276(3) Uani 1 1 d . . . . .
H10 H 0.544428 1.278762 0.442609 0.033 Uiso 1 1 calc R U . . .
C28 C 0.62991(11) 0.89601(15) 0.05432(7) 0.0369(3) Uani 1 1 d . . . . .
H28A H 0.557576 0.904090 0.030275 0.055 Uiso 1 1 calc R U . . .
H28B H 0.667453 0.859568 0.015206 0.055 Uiso 1 1 calc R U . . .
H28C H 0.656539 0.989240 0.072454 0.055 Uiso 1 1 calc R U . . .
C26 C 0.88679(10) 0.87196(15) 0.53733(8) 0.0353(3) Uani 1 1 d . . . . .
H26A H 0.917045 0.888665 0.490848 0.053 Uiso 1 1 calc R U . . .
H26B H 0.934525 0.818151 0.576672 0.053 Uiso 1 1 calc R U . . .
H26C H 0.872096 0.962740 0.560022 0.053 Uiso 1 1 calc R U . . .
B1 B 0.56322(9) 0.81580(13) 0.33260(7) 0.0193(2) Uani 1 1 d . . . . .
C27 C 0.53645(10) 1.26647(13) 0.17161(7) 0.0296(3) Uani 1 1 d . . . . .
H27A H 0.603792 1.257713 0.157864 0.044 Uiso 1 1 calc R U . . .
H27B H 0.516363 1.366163 0.169748 0.044 Uiso 1 1 calc R U . . .
H27C H 0.486723 1.212490 0.133864 0.044 Uiso 1 1 calc R U . . .
C18 C 0.78740(9) 0.78770(13) 0.51294(7) 0.0251(2) Uani 1 1 d . . . . .
H13 H 0.5583(13) 1.0012(19) 0.2189(10) 0.049(4) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N13 C8 1.3567(13) . ?
N13 C12 1.3520(14) . ?
N13 H13 0.986(17) . ?
N6 C1 1.3622(14) . ?
N6 C5 1.3525(14) . ?
N19 C14 1.3620(14) . ?
N19 C18 1.3467(15) . ?
C8 C9 1.3998(15) . ?
C8 B1 1.6310(16) . ?
C14 C15 1.3976(15) . ?
C14 B1 1.6361(15) . ?
C9 H9 0.9300 . ?
C9 C10 1.3802(17) . ?
C20 C21 1.3953(16) . ?
C20 C25 1.4068(15) . ?
C20 B1 1.6465(15) . ?
C3 H3 0.9300 . ?
C3 C2 1.3880(16) . ?
C3 C4 1.3864(17) . ?
C21 H21 0.9300 . ?
C21 C22 1.3968(16) . ?
C2 H2 0.9300 . ?
C2 C1 1.3991(15) . ?
C15 H15 0.9300 . ?
C15 C16 1.3918(16) . ?
C16 H16 0.9300 . ?
C16 C17 1.3831(17) . ?
C17 H17 0.9300 . ?
C17 C18 1.3937(17) . ?
C1 B1 1.6416(15) . ?
C11 H11 0.9300 . ?
C11 C12 1.3786(16) . ?
C11 C10 1.3930(17) . ?
C25 H25 0.9300 . ?
C25 C24 1.3914(16) . ?
C24 H24 0.9300 . ?
C24 C23 1.3856(19) . ?
C23 H23 0.9300 . ?
C23 C22 1.3820(19) . ?
C22 H22 0.9300 . ?
C12 C27 1.4996(16) . ?
C4 H4 0.9300 . ?
C4 C5 1.3802(17) . ?
C5 C28 1.5035(16) . ?
C10 H10 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C26 C18 1.5073(16) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 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
C8 N13 H13 112.8(10) . . ?
C12 N13 C8 125.71(10) . . ?
C12 N13 H13 121.2(10) . . ?
C5 N6 C1 121.39(9) . . ?
C18 N19 C14 119.62(10) . . ?
N13 C8 C9 115.92(10) . . ?
N13 C8 B1 118.22(9) . . ?
C9 C8 B1 125.80(10) . . ?
N19 C14 C15 119.71(10) . . ?
N19 C14 B1 116.26(9) . . ?
C15 C14 B1 124.01(9) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.65(11) . . ?
C10 C9 H9 119.7 . . ?
C21 C20 C25 115.57(10) . . ?
C21 C20 B1 123.35(10) . . ?
C25 C20 B1 121.05(10) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C4 C3 C2 119.45(10) . . ?
C20 C21 H21 118.7 . . ?
C20 C21 C22 122.56(11) . . ?
C22 C21 H21 118.7 . . ?
C3 C2 H2 119.7 . . ?
C3 C2 C1 120.50(10) . . ?
C1 C2 H2 119.7 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.60(10) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 118.91(11) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 120.8 . . ?
C16 C17 C18 118.49(10) . . ?
C18 C17 H17 120.8 . . ?
N6 C1 C2 118.42(10) . . ?
N6 C1 B1 119.09(9) . . ?
C2 C1 B1 122.37(9) . . ?
C12 C11 H11 120.4 . . ?
C12 C11 C10 119.19(11) . . ?
C10 C11 H11 120.4 . . ?
C20 C25 H25 118.7 . . ?
C24 C25 C20 122.58(11) . . ?
C24 C25 H25 118.7 . . ?
C25 C24 H24 120.0 . . ?
C23 C24 C25 119.93(11) . . ?
C23 C24 H24 120.0 . . ?
C24 C23 H23 120.4 . . ?
C22 C23 C24 119.28(11) . . ?
C22 C23 H23 120.4 . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 120.08(12) . . ?
C23 C22 H22 120.0 . . ?
N13 C12 C11 118.17(10) . . ?
N13 C12 C27 116.61(10) . . ?
C11 C12 C27 125.22(10) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.79(10) . . ?
C5 C4 H4 120.6 . . ?
N6 C5 C4 121.33(10) . . ?
N6 C5 C28 116.42(10) . . ?
C4 C5 C28 122.25(10) . . ?
C9 C10 C11 120.33(11) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C5 C28 H28A 109.5 . . ?
C5 C28 H28B 109.5 . . ?
C5 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C18 C26 H26A 109.5 . . ?
C18 C26 H26B 109.5 . . ?
C18 C26 H26C 109.5 . . ?
C8 B1 C14 108.62(9) . . ?
C8 B1 C20 106.89(9) . . ?
C8 B1 C1 111.41(9) . . ?
C14 B1 C20 111.39(8) . . ?
C14 B1 C1 109.00(8) . . ?
C1 B1 C20 109.53(8) . . ?
C12 C27 H27A 109.5 . . ?
C12 C27 H27B 109.5 . . ?
C12 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N19 C18 C17 122.66(11) . . ?
N19 C18 C26 115.90(10) . . ?
C17 C18 C26 121.44(10) . . ?

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
N13 C8 C9 C10 1.19(15) . . . . ?
N13 C8 B1 C14 149.18(9) . . . . ?
N13 C8 B1 C20 -90.52(10) . . . . ?
N13 C8 B1 C1 29.10(13) . . . . ?
N6 C1 B1 C8 -29.65(13) . . . . ?
N6 C1 B1 C14 -149.50(9) . . . . ?
N6 C1 B1 C20 88.40(11) . . . . ?
N19 C14 C15 C16 1.63(16) . . . . ?
N19 C14 B1 C8 -47.16(12) . . . . ?
N19 C14 B1 C20 -164.63(9) . . . . ?
N19 C14 B1 C1 74.40(11) . . . . ?
C8 N13 C12 C11 -1.52(16) . . . . ?
C8 N13 C12 C27 177.67(10) . . . . ?
C8 C9 C10 C11 -0.58(17) . . . . ?
C14 N19 C18 C17 0.33(17) . . . . ?
C14 N19 C18 C26 -178.80(10) . . . . ?
C14 C15 C16 C17 -0.34(17) . . . . ?
C9 C8 B1 C14 -33.73(14) . . . . ?
C9 C8 B1 C20 86.58(12) . . . . ?
C9 C8 B1 C1 -153.80(10) . . . . ?
C20 C21 C22 C23 0.25(19) . . . . ?
C20 C25 C24 C23 -0.28(18) . . . . ?
C3 C2 C1 N6 -2.34(15) . . . . ?
C3 C2 C1 B1 173.74(10) . . . . ?
C3 C4 C5 N6 -2.67(16) . . . . ?
C3 C4 C5 C28 178.22(11) . . . . ?
C21 C20 C25 C24 0.55(16) . . . . ?
C21 C20 B1 C8 132.37(11) . . . . ?
C21 C20 B1 C14 -109.12(11) . . . . ?
C21 C20 B1 C1 11.54(14) . . . . ?
C2 C3 C4 C5 -0.41(16) . . . . ?
C2 C1 B1 C8 154.29(10) . . . . ?
C2 C1 B1 C14 34.44(13) . . . . ?
C2 C1 B1 C20 -87.66(12) . . . . ?
C15 C14 B1 C8 134.37(10) . . . . ?
C15 C14 B1 C20 16.90(14) . . . . ?
C15 C14 B1 C1 -104.07(11) . . . . ?
C15 C16 C17 C18 -0.92(17) . . . . ?
C16 C17 C18 N19 0.96(18) . . . . ?
C16 C17 C18 C26 -179.96(11) . . . . ?
C1 N6 C5 C4 3.28(16) . . . . ?
C1 N6 C5 C28 -177.56(10) . . . . ?
C25 C20 C21 C22 -0.54(16) . . . . ?
C25 C20 B1 C8 -49.71(12) . . . . ?
C25 C20 B1 C14 68.80(13) . . . . ?
C25 C20 B1 C1 -170.54(9) . . . . ?
C25 C24 C23 C22 -0.04(18) . . . . ?
C24 C23 C22 C21 0.06(19) . . . . ?
C12 N13 C8 C9 -0.13(15) . . . . ?
C12 N13 C8 B1 177.25(10) . . . . ?
C12 C11 C10 C9 -1.10(18) . . . . ?
C4 C3 C2 C1 2.89(16) . . . . ?
C5 N6 C1 C2 -0.73(15) . . . . ?
C5 N6 C1 B1 -176.95(9) . . . . ?
C10 C11 C12 N13 2.09(16) . . . . ?
C10 C11 C12 C27 -177.03(11) . . . . ?
B1 C8 C9 C10 -175.97(10) . . . . ?
B1 C14 C15 C16 -179.95(10) . . . . ?
B1 C20 C21 C22 177.48(11) . . . . ?
B1 C20 C25 C24 -177.52(10) . . . . ?
C18 N19 C14 C15 -1.61(16) . . . . ?
C18 N19 C14 B1 179.85(9) . . . . ?

_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 1.203
_oxdiff_exptl_absorpt_empirical_full_min 0.870
####################################################################### 
# 
# 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_[NiCl(TpyMe)]
_database_code_depnum_ccdc_archive 'CCDC 2172879'
loop_
_audit_author_name
_audit_author_address
'Shiro Hikichi'
;Kanagawa University
Japan
;
_audit_update_record             
;
2022-05-16 deposited with the CCDC.	2022-05-30 downloaded from the CCDC.
;
_audit_creation_date             2022-01-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6380)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H23 B Cl N3 Ni'
_chemical_formula_sum            'C24 H23 B Cl N3 Ni'
_chemical_formula_weight         458.42
_chemical_melting_point          ?
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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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'
Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.03974(17)
_cell_length_b                   15.8652(2)
_cell_length_c                   13.3756(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.3207(15)
_cell_angle_gamma                90
_cell_volume                     2130.47(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9579
_cell_measurement_temperature    90
_cell_measurement_theta_max      76.5980
_cell_measurement_theta_min      5.5030
_shelx_estimated_absorpt_T_max   0.811
_shelx_estimated_absorpt_T_min   0.701
_exptl_absorpt_coefficient_mu    2.578
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93203
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.148
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.085
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12755
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.791
_diffrn_reflns_theta_min         4.323
_diffrn_ambient_temperature      90.00
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    100.00 132.00   0.50    0.20    --  104.75  15.00  30.00   64
  2  ω     99.00 170.00   0.50    0.20    --  104.75  15.00 120.00  142
  3  ω    144.00 173.00   0.50    0.20    --  104.75  15.00  30.00   58
  4  ω     58.00 107.00   0.50    0.05    --   46.27  65.00-176.00   98
  5  ω    -14.00  24.00   0.50    0.05    --  -46.27  19.00  60.00   76
  6  ω    -60.00 -32.00   0.50    0.20    -- -102.00  61.00  30.00   56
  7  ω   -160.00-111.00   0.50    0.20    -- -102.00 -69.00 -84.00   98
  8  ω    -55.00 -30.00   0.50    0.20    -- -102.00  61.00-180.00   50
  9  ω    -93.00 -14.00   0.50    0.05    --  -46.27 125.00  60.00  158
 10  ω     37.00  62.00   0.50    0.20    --  104.75 -45.00 -90.00   50
 11  ω     33.00  58.00   0.50    0.20    --  104.75 -45.00 -60.00   50
 12  ω     34.00  60.00   0.50    0.20    --  104.75 -45.00-120.00   52
 13  ω     33.00  58.00   0.50    0.20    --  104.75 -45.00-180.00   50
 14  ω    -25.00  66.00   0.50    0.05    --   46.27 -69.00 -84.00  182
 15  ω     52.00  77.00   0.50    0.20    --  104.75 -65.00  48.00   50
 16  ω     37.00  92.00   0.50    0.20    --  104.75-125.00 150.00  110
 17  ω     32.00 105.00   0.50    0.20    --  104.75 -89.00 172.00  146
 18  ω     75.00 105.00   0.50    0.20    --  104.75 -94.00  90.00   60
 19  ω     32.00 105.00   0.50    0.20    --  104.75 -94.00 -90.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3755
_reflns_number_total             4165
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0320
_refine_ls_restrained_S_all      1.079
_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)+(0.0403P)²+0.6793P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0852
_refine_special_details          ?
_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 Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8), C7(H7), C21(H21), C17(H17), C20(H20), C14(H14), C4(H4),
 C2(H2), C19(H19), C3(H3), C18(H18), C13(H13), C12(H12)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.23959(3) 0.56425(2) 0.18594(2) 0.02132(10) Uani 1 1 d . . . . .
Cl1 Cl 0.23705(5) 0.58226(3) 0.02132(3) 0.03452(12) Uani 1 1 d . . . . .
N1 N 0.10241(13) 0.62769(8) 0.26667(10) 0.0207(3) Uani 1 1 d . . . . .
N2 N 0.23039(13) 0.46334(8) 0.27044(10) 0.0210(3) Uani 1 1 d . . . . .
N3 N 0.40222(14) 0.60809(8) 0.25984(10) 0.0227(3) Uani 1 1 d . . . . .
C10 C 0.24026(15) 0.47790(9) 0.37061(11) 0.0195(3) Uani 1 1 d . . . . .
C5 C 0.13245(15) 0.63443(9) 0.36594(12) 0.0207(3) Uani 1 1 d . . . . .
C1 C 0.00352(16) 0.67510(10) 0.22489(12) 0.0254(3) Uani 1 1 d . . . . .
C9 C 0.24056(16) 0.40795(10) 0.43434(12) 0.0226(3) Uani 1 1 d . . . . .
H9 H 0.247469 0.416156 0.504536 0.027 Uiso 1 1 calc R U . . .
C6 C 0.21951(17) 0.38469(10) 0.23213(12) 0.0246(3) Uani 1 1 d . . . . .
C8 C 0.23093(17) 0.32695(10) 0.39648(13) 0.0255(3) Uani 1 1 d . . . . .
H8 H 0.231917 0.279872 0.440365 0.031 Uiso 1 1 calc R U . . .
C15 C 0.38286(16) 0.62091(9) 0.35978(12) 0.0213(3) Uani 1 1 d . . . . .
C16 C 0.25657(16) 0.57232(9) 0.53260(12) 0.0212(3) Uani 1 1 d . . . . .
C7 C 0.21987(18) 0.31503(10) 0.29432(13) 0.0269(3) Uani 1 1 d . . . . .
H7 H 0.212629 0.259843 0.267278 0.032 Uiso 1 1 calc R U . . .
C21 C 0.37497(17) 0.56325(9) 0.58806(12) 0.0226(3) Uani 1 1 d . . . . .
H21 H 0.457634 0.564549 0.553879 0.027 Uiso 1 1 calc R U . . .
C17 C 0.13854(18) 0.56541(10) 0.58773(13) 0.0269(4) Uani 1 1 d . . . . .
H17 H 0.055707 0.568509 0.553247 0.032 Uiso 1 1 calc R U . . .
C20 C 0.37537(18) 0.55243(11) 0.69148(13) 0.0273(3) Uani 1 1 d . . . . .
H20 H 0.457649 0.547734 0.726457 0.033 Uiso 1 1 calc R U . . .
C14 C 0.46764(18) 0.67649(11) 0.41013(13) 0.0278(3) Uani 1 1 d . . . . .
H14 H 0.453535 0.687740 0.479023 0.033 Uiso 1 1 calc R U . . .
C4 C 0.06839(17) 0.69699(10) 0.42175(13) 0.0270(3) Uani 1 1 d . . . . .
H4 H 0.089028 0.703082 0.490774 0.032 Uiso 1 1 calc R U . . .
C2 C -0.05867(17) 0.73786(11) 0.27932(14) 0.0299(4) Uani 1 1 d . . . . .
H2 H -0.124629 0.772313 0.248662 0.036 Uiso 1 1 calc R U . . .
C19 C 0.2567(2) 0.54847(12) 0.74364(13) 0.0314(4) Uani 1 1 d . . . . .
H19 H 0.256851 0.541940 0.814244 0.038 Uiso 1 1 calc R U . . .
C22 C -0.0389(2) 0.65754(13) 0.11915(14) 0.0358(4) Uani 1 1 d . . . . .
H22A H 0.030120 0.677211 0.073220 0.054 Uiso 1 1 calc R U . . .
H22B H -0.122565 0.687162 0.104853 0.054 Uiso 1 1 calc R U . . .
H22C H -0.052122 0.596782 0.110338 0.054 Uiso 1 1 calc R U . . .
C3 C -0.02456(18) 0.75011(11) 0.37796(15) 0.0322(4) Uani 1 1 d . . . . .
H3 H -0.064091 0.794286 0.415450 0.039 Uiso 1 1 calc R U . . .
C11 C 0.51192(18) 0.63947(12) 0.21348(13) 0.0312(4) Uani 1 1 d . . . . .
C18 C 0.13807(19) 0.55419(12) 0.69098(13) 0.0319(4) Uani 1 1 d . . . . .
H18 H 0.055808 0.550446 0.725460 0.038 Uiso 1 1 calc R U . . .
C13 C 0.5721(2) 0.71550(13) 0.36105(15) 0.0392(4) Uani 1 1 d . . . . .
H13 H 0.626076 0.755964 0.394424 0.047 Uiso 1 1 calc R U . . .
C23 C 0.2053(2) 0.37637(12) 0.12069(14) 0.0374(4) Uani 1 1 d . . . . .
H23A H 0.122415 0.403422 0.098807 0.056 Uiso 1 1 calc R U . . .
H23B H 0.203304 0.316549 0.102481 0.056 Uiso 1 1 calc R U . . .
H23C H 0.281092 0.403713 0.088077 0.056 Uiso 1 1 calc R U . . .
C12 C 0.5960(2) 0.69436(15) 0.26278(15) 0.0419(5) Uani 1 1 d . . . . .
H12 H 0.670470 0.717636 0.229043 0.050 Uiso 1 1 calc R U . . .
C24 C 0.5419(2) 0.61176(16) 0.10884(15) 0.0437(5) Uani 1 1 d . . . . .
H24A H 0.520374 0.551822 0.101460 0.065 Uiso 1 1 calc R U . . .
H24B H 0.636669 0.620568 0.095114 0.065 Uiso 1 1 calc R U . . .
H24C H 0.488272 0.644763 0.061554 0.065 Uiso 1 1 calc R U . . .
B1 B 0.25287(18) 0.57548(10) 0.41064(13) 0.0194(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 Cl1 2.2204(5) . ?
Ni1 N1 2.0229(13) . ?
Ni1 N2 1.9623(13) . ?
Ni1 N3 2.0269(14) . ?
N1 C5 1.364(2) . ?
N1 C1 1.363(2) . ?
N2 C10 1.363(2) . ?
N2 C6 1.353(2) . ?
N3 C15 1.367(2) . ?
N3 C11 1.361(2) . ?
C10 C9 1.399(2) . ?
C10 B1 1.643(2) . ?
C5 C4 1.400(2) . ?
C5 B1 1.639(2) . ?
C1 C2 1.384(3) . ?
C1 C22 1.501(3) . ?
C9 H9 0.9500 . ?
C9 C8 1.384(2) . ?
C6 C7 1.383(2) . ?
C6 C23 1.502(2) . ?
C8 H8 0.9500 . ?
C8 C7 1.383(2) . ?
C15 C14 1.396(2) . ?
C15 B1 1.642(2) . ?
C16 C21 1.405(2) . ?
C16 C17 1.403(2) . ?
C16 B1 1.632(2) . ?
C7 H7 0.9500 . ?
C21 H21 0.9500 . ?
C21 C20 1.394(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.393(3) . ?
C20 H20 0.9500 . ?
C20 C19 1.385(3) . ?
C14 H14 0.9500 . ?
C14 C13 1.386(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.385(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.375(3) . ?
C19 H19 0.9500 . ?
C19 C18 1.384(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C3 H3 0.9500 . ?
C11 C12 1.378(3) . ?
C11 C24 1.499(3) . ?
C18 H18 0.9500 . ?
C13 H13 0.9500 . ?
C13 C12 1.379(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C12 H12 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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 Cl1 117.47(4) . . ?
N1 Ni1 N3 96.78(5) . . ?
N2 Ni1 Cl1 132.52(4) . . ?
N2 Ni1 N1 93.68(5) . . ?
N2 Ni1 N3 92.26(6) . . ?
N3 Ni1 Cl1 116.37(4) . . ?
C5 N1 Ni1 114.27(10) . . ?
C1 N1 Ni1 123.52(11) . . ?
C1 N1 C5 120.82(14) . . ?
C10 N2 Ni1 115.13(10) . . ?
C6 N2 Ni1 122.57(11) . . ?
C6 N2 C10 122.27(13) . . ?
C15 N3 Ni1 114.17(10) . . ?
C11 N3 Ni1 123.71(11) . . ?
C11 N3 C15 120.71(15) . . ?
N2 C10 C9 117.68(14) . . ?
N2 C10 B1 119.02(13) . . ?
C9 C10 B1 123.30(14) . . ?
N1 C5 C4 118.34(14) . . ?
N1 C5 B1 117.97(13) . . ?
C4 C5 B1 123.37(14) . . ?
N1 C1 C2 120.73(15) . . ?
N1 C1 C22 119.10(15) . . ?
C2 C1 C22 120.17(16) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 C10 120.89(15) . . ?
C8 C9 H9 119.6 . . ?
N2 C6 C7 120.61(15) . . ?
N2 C6 C23 117.63(14) . . ?
C7 C6 C23 121.76(15) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 C9 119.56(15) . . ?
C7 C8 H8 120.2 . . ?
N3 C15 C14 118.43(14) . . ?
N3 C15 B1 117.22(13) . . ?
C14 C15 B1 124.14(14) . . ?
C21 C16 B1 123.04(14) . . ?
C17 C16 C21 115.40(15) . . ?
C17 C16 B1 120.86(15) . . ?
C6 C7 C8 118.99(15) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C16 C21 H21 118.9 . . ?
C20 C21 C16 122.30(16) . . ?
C20 C21 H21 118.9 . . ?
C16 C17 H17 118.7 . . ?
C18 C17 C16 122.59(17) . . ?
C18 C17 H17 118.7 . . ?
C21 C20 H20 119.7 . . ?
C19 C20 C21 120.51(16) . . ?
C19 C20 H20 119.7 . . ?
C15 C14 H14 119.5 . . ?
C13 C14 C15 120.95(16) . . ?
C13 C14 H14 119.5 . . ?
C5 C4 H4 119.5 . . ?
C3 C4 C5 121.08(16) . . ?
C3 C4 H4 119.5 . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.71(16) . . ?
C3 C2 H2 120.1 . . ?
C20 C19 H19 120.6 . . ?
C18 C19 C20 118.75(16) . . ?
C18 C19 H19 120.6 . . ?
C1 C22 H22A 109.5 . . ?
C1 C22 H22B 109.5 . . ?
C1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C4 C3 H3 120.5 . . ?
C2 C3 C4 118.91(16) . . ?
C2 C3 H3 120.5 . . ?
N3 C11 C12 120.55(17) . . ?
N3 C11 C24 119.02(17) . . ?
C12 C11 C24 120.41(17) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.37(17) . . ?
C19 C18 H18 119.8 . . ?
C14 C13 H13 120.7 . . ?
C12 C13 C14 118.63(18) . . ?
C12 C13 H13 120.7 . . ?
C6 C23 H23A 109.5 . . ?
C6 C23 H23B 109.5 . . ?
C6 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C11 C12 C13 120.01(17) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C11 C24 H24A 109.5 . . ?
C11 C24 H24B 109.5 . . ?
C11 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C5 B1 C10 111.32(13) . . ?
C5 B1 C15 100.65(12) . . ?
C15 B1 C10 109.80(12) . . ?
C16 B1 C10 107.33(12) . . ?
C16 B1 C5 113.25(13) . . ?
C16 B1 C15 114.45(13) . . ?

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 N1 C5 C4 160.87(12) . . . . ?
Ni1 N1 C5 B1 -12.82(16) . . . . ?
Ni1 N1 C1 C2 -158.51(13) . . . . ?
Ni1 N1 C1 C22 22.4(2) . . . . ?
Ni1 N2 C10 C9 -177.10(11) . . . . ?
Ni1 N2 C10 B1 2.20(17) . . . . ?
Ni1 N2 C6 C7 176.83(13) . . . . ?
Ni1 N2 C6 C23 -4.0(2) . . . . ?
Ni1 N3 C15 C14 -158.07(12) . . . . ?
Ni1 N3 C15 B1 16.99(17) . . . . ?
Ni1 N3 C11 C12 156.62(15) . . . . ?
Ni1 N3 C11 C24 -24.9(2) . . . . ?
N1 C5 C4 C3 0.9(2) . . . . ?
N1 C5 B1 C10 -45.40(18) . . . . ?
N1 C5 B1 C15 70.92(16) . . . . ?
N1 C5 B1 C16 -166.45(13) . . . . ?
N1 C1 C2 C3 -2.9(3) . . . . ?
N2 C10 C9 C8 -0.1(2) . . . . ?
N2 C10 B1 C5 53.21(18) . . . . ?
N2 C10 B1 C15 -57.36(18) . . . . ?
N2 C10 B1 C16 177.67(13) . . . . ?
N2 C6 C7 C8 0.3(3) . . . . ?
N3 C15 C14 C13 -2.3(3) . . . . ?
N3 C15 B1 C10 43.91(18) . . . . ?
N3 C15 B1 C5 -73.53(16) . . . . ?
N3 C15 B1 C16 164.68(13) . . . . ?
N3 C11 C12 C13 2.4(3) . . . . ?
C10 N2 C6 C7 -0.9(2) . . . . ?
C10 N2 C6 C23 178.30(16) . . . . ?
C10 C9 C8 C7 -0.5(2) . . . . ?
C5 N1 C1 C2 7.3(2) . . . . ?
C5 N1 C1 C22 -171.74(15) . . . . ?
C5 C4 C3 C2 3.3(3) . . . . ?
C1 N1 C5 C4 -6.2(2) . . . . ?
C1 N1 C5 B1 -179.87(13) . . . . ?
C1 C2 C3 C4 -2.3(3) . . . . ?
C9 C10 B1 C5 -127.52(15) . . . . ?
C9 C10 B1 C15 121.90(16) . . . . ?
C9 C10 B1 C16 -3.1(2) . . . . ?
C9 C8 C7 C6 0.4(3) . . . . ?
C6 N2 C10 C9 0.8(2) . . . . ?
C6 N2 C10 B1 -179.90(14) . . . . ?
C15 N3 C11 C12 -9.0(3) . . . . ?
C15 N3 C11 C24 169.46(16) . . . . ?
C15 C14 C13 C12 -4.0(3) . . . . ?
C16 C21 C20 C19 1.3(2) . . . . ?
C16 C17 C18 C19 -0.7(3) . . . . ?
C21 C16 C17 C18 2.8(2) . . . . ?
C21 C16 B1 C10 88.32(17) . . . . ?
C21 C16 B1 C5 -148.40(14) . . . . ?
C21 C16 B1 C15 -33.8(2) . . . . ?
C21 C20 C19 C18 1.0(3) . . . . ?
C17 C16 C21 C20 -3.1(2) . . . . ?
C17 C16 B1 C10 -81.65(17) . . . . ?
C17 C16 B1 C5 41.62(19) . . . . ?
C17 C16 B1 C15 156.23(14) . . . . ?
C20 C19 C18 C17 -1.3(3) . . . . ?
C14 C15 B1 C10 -141.33(15) . . . . ?
C14 C15 B1 C5 101.22(17) . . . . ?
C14 C15 B1 C16 -20.6(2) . . . . ?
C14 C13 C12 C11 4.0(3) . . . . ?
C4 C5 B1 C10 141.26(15) . . . . ?
C4 C5 B1 C15 -102.42(17) . . . . ?
C4 C5 B1 C16 20.2(2) . . . . ?
C22 C1 C2 C3 176.13(17) . . . . ?
C11 N3 C15 C14 8.8(2) . . . . ?
C11 N3 C15 B1 -176.09(14) . . . . ?
C23 C6 C7 C8 -178.89(17) . . . . ?
C24 C11 C12 C13 -176.0(2) . . . . ?
B1 C10 C9 C8 -179.37(15) . . . . ?
B1 C5 C4 C3 174.19(15) . . . . ?
B1 C15 C14 C13 -177.03(17) . . . . ?
B1 C16 C21 C20 -173.61(14) . . . . ?
B1 C16 C17 C18 173.52(15) . . . . ?

_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
;
####################################################################### 
# 
# 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_[CoCl2[PhB(OEt)(pyMe)(HpyMe)]]
_database_code_depnum_ccdc_archive 'CCDC 2172876'
loop_
_audit_author_name
_audit_author_address
'Shiro Hikichi'
;Kanagawa University
Japan
;
_audit_update_record             
;
2022-05-16 deposited with the CCDC.	2022-05-30 downloaded from the CCDC.
;
_audit_creation_date             2022-01-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6380)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H23 B Cl2 Co N2 O'
_chemical_formula_sum            'C20 H23 B Cl2 Co N2 O'
_chemical_formula_weight         448.04
_chemical_melting_point          ?
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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   7.3720(2)
_cell_length_b                   26.7621(6)
_cell_length_c                   11.1119(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.356(3)
_cell_angle_gamma                90
_cell_volume                     2080.72(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17438
_cell_measurement_temperature    90
_cell_measurement_theta_max      76.2530
_cell_measurement_theta_min      3.2230
_shelx_estimated_absorpt_T_max   0.200
_shelx_estimated_absorpt_T_min   0.128
_exptl_absorpt_coefficient_mu    8.917
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74143
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.114a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             924
_exptl_crystal_size_max          0.392
_exptl_crystal_size_mid          0.289
_exptl_crystal_size_min          0.266
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            27044
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.516
_diffrn_reflns_theta_min         3.303
_diffrn_ambient_temperature      90.00
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     98.00 171.00   0.50    0.05    --  104.15  45.00 150.00  146
  2  ω    103.00 129.00   0.50    0.05    --  104.15  45.00 -30.00   52
  3  ω    109.00 149.00   0.50    0.05    --  104.15  75.00-150.00   80
  4  ω     57.00 102.00   0.50    0.05    --   46.17  75.00-150.00   90
  5  ω    -62.00  -5.00   0.50    0.05    --  -46.17  75.00-150.00  114
  6  ω    -19.00  23.00   0.50    0.05    --  -46.17  19.00-180.00   84
  7  ω    -18.00  29.00   0.50    0.05    --  -46.17  19.00-150.00   94
  8  ω    -19.00  29.00   0.50    0.05    --  -46.17  19.00   0.00   96
  9  ω    -59.00   8.00   0.50    0.05    --  -46.17  57.00  60.00  134
 10  ω    -13.00  28.00   0.50    0.05    --  -46.17  19.00 120.00   82
 11  ω    -19.00  29.00   0.50    0.05    --  -46.17  19.00  90.00   96
 12  ω    -90.00 -65.00   0.50    0.05    -- -102.00  75.00-150.00   50
 13  ω    -67.00 -29.00   0.50    0.05    -- -102.00  61.00-180.00   76
 14  ω    -62.00 -29.00   0.50    0.05    -- -102.00  61.00 -90.00   66
 15  ω    -68.00 -31.00   0.50    0.05    -- -102.00  61.00  30.00   74
 16  ω    -70.00 -29.00   0.50    0.05    -- -102.00  61.00  60.00   82
 17  ω    -64.00 -34.00   0.50    0.05    -- -102.00  61.00  90.00   60
 18  ω    -62.00 -29.00   0.50    0.05    -- -102.00 125.00  30.00   66
 19  ω   -104.00 -74.00   0.50    0.05    -- -102.00 125.00  30.00   60
 20  ω   -116.00 -91.00   0.50    0.05    -- -102.00 -61.00   0.00   50
 21  ω   -169.00-129.00   0.50    0.05    -- -102.00 -61.00   0.00   80
 22  ω   -172.00 -89.00   0.50    0.05    -- -102.00 -45.00 -60.00  166
 23  ω   -171.00 -90.00   0.50    0.05    -- -102.00 -45.00 -30.00  162
 24  ω   -154.00 -89.00   0.50    0.05    -- -102.00 -15.00 -30.00  130
 25  ω   -173.00 -89.00   0.50    0.05    -- -102.00 -30.00  30.00  168
 26  ω   -154.00-118.00   0.50    0.05    -- -102.00 -75.00  81.00   72
 27  ω    -95.00 -70.00   0.50    0.05    --  -46.17 -75.00  81.00   50
 28  ω    -23.00  22.00   0.50    0.05    --   46.17 -19.00-180.00   90
 29  ω     36.00  73.00   0.50    0.05    --  104.15 -77.00-150.00   74
 30  ω     85.00 127.00   0.50    0.05    --  104.15 -77.00-150.00   84
 31  ω    -23.00  39.00   0.50    0.05    --   46.17 -75.00  81.00  124
 32  ω     33.00  75.00   0.50    0.05    --  104.15 -75.00  81.00   84
 33  ω     79.00 108.00   0.50    0.05    --  104.15 -75.00  81.00   58
 34  ω     35.00  75.00   0.50    0.05    --  104.15 -61.00  90.00   80
 35  ω     47.00 106.00   0.50    0.05    --  104.15 -94.00 -30.00  118
 36  ω     71.00 105.00   0.50    0.05    --  104.15 -94.00 -90.00   68
 37  ω     33.00 103.00   0.50    0.05    --  104.15-125.00 -90.00  140
 38  ω     39.00  64.00   0.50    0.05    --  104.15-125.00-120.00   50
 39  ω     51.00  86.00   0.50    0.05    --  104.15 -94.00-180.00   70
 40  ω     81.00 106.00   0.50    0.05    --  104.15-125.00-120.00   50
 41  ω     37.00  63.00   0.50    0.05    --  104.15 -94.00  30.00   52
 42  ω     75.00 102.00   0.50    0.05    --  104.15 -94.00  30.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4157
_reflns_number_total             4250
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.114a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.114a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.114a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0323
_refine_ls_restrained_S_all      1.096
_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)+(0.0338P)²+2.2650P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0800
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C4(H4), C12(H12), C3(H3), C14(H14), C13(H13), C16(H16),
 C15(H15), C9(H9), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
Co1 Co 0.30021(4) 0.64013(2) 0.44660(3) 0.01051(9) Uani 1 1 d . . . . .
Cl2 Cl 0.38101(7) 0.71868(2) 0.40827(5) 0.02041(12) Uani 1 1 d . . . . .
Cl1 Cl 0.05385(6) 0.61003(2) 0.28912(4) 0.01841(11) Uani 1 1 d . . . . .
O1 O 0.28151(18) 0.64647(5) 0.62046(12) 0.0115(3) Uani 1 1 d . . . . .
N1 N 0.5139(2) 0.59169(6) 0.52684(15) 0.0105(3) Uani 1 1 d . . . . .
N2 N 0.5889(2) 0.70820(6) 0.72808(16) 0.0151(3) Uani 1 1 d . . . . .
H2 H 0.489937 0.712246 0.659544 0.018 Uiso 1 1 calc R U . . .
C1 C 0.6103(2) 0.56553(7) 0.46202(18) 0.0120(4) Uani 1 1 d . . . . .
C2 C 0.7402(3) 0.52885(7) 0.52261(19) 0.0156(4) Uani 1 1 d . . . . .
H2A H 0.806914 0.510385 0.476808 0.019 Uiso 1 1 calc R U . . .
C5 C 0.5455(3) 0.58401(7) 0.65315(18) 0.0120(4) Uani 1 1 d . . . . .
C17 C 0.5706(3) 0.57847(7) 0.32509(19) 0.0160(4) Uani 1 1 d . . . . .
H17A H 0.454365 0.561293 0.274206 0.024 Uiso 1 1 calc R U . . .
H17B H 0.678574 0.567935 0.297509 0.024 Uiso 1 1 calc R U . . .
H17C H 0.552953 0.614665 0.313904 0.024 Uiso 1 1 calc R U . . .
C4 C 0.6760(3) 0.54740(7) 0.71564(19) 0.0159(4) Uani 1 1 d . . . . .
H4 H 0.699167 0.541712 0.803599 0.019 Uiso 1 1 calc R U . . .
C12 C 0.2992(3) 0.54488(8) 0.81597(19) 0.0185(4) Uani 1 1 d . . . . .
H12 H 0.311732 0.526011 0.746592 0.022 Uiso 1 1 calc R U . . .
C3 C 0.7721(3) 0.51929(7) 0.6502(2) 0.0182(4) Uani 1 1 d . . . . .
H3 H 0.858692 0.493812 0.692254 0.022 Uiso 1 1 calc R U . . .
C19 C 0.1426(3) 0.67831(7) 0.64909(18) 0.0146(4) Uani 1 1 d . . . . .
H19A H 0.140689 0.711344 0.608593 0.017 Uiso 1 1 calc R U . . .
H19B H 0.178228 0.683383 0.741882 0.017 Uiso 1 1 calc R U . . .
C11 C 0.3600(3) 0.59451(7) 0.82934(18) 0.0142(4) Uani 1 1 d . . . . .
C14 C 0.1962(3) 0.54955(9) 1.0010(2) 0.0244(5) Uani 1 1 d . . . . .
H14 H 0.139778 0.534574 1.058089 0.029 Uiso 1 1 calc R U . . .
C10 C 0.6003(3) 0.66433(7) 0.78975(18) 0.0145(4) Uani 1 1 d . . . . .
C13 C 0.2207(3) 0.52199(9) 0.9009(2) 0.0241(5) Uani 1 1 d . . . . .
H13 H 0.184262 0.487815 0.890616 0.029 Uiso 1 1 calc R U . . .
C16 C 0.3367(3) 0.62094(8) 0.93276(19) 0.0191(4) Uani 1 1 d . . . . .
H16 H 0.378105 0.654704 0.945891 0.023 Uiso 1 1 calc R U . . .
C15 C 0.2544(3) 0.59877(9) 1.0165(2) 0.0241(5) Uani 1 1 d . . . . .
H15 H 0.238319 0.617692 1.084779 0.029 Uiso 1 1 calc R U . . .
C6 C 0.7147(3) 0.74678(8) 0.7609(2) 0.0221(5) Uani 1 1 d . . . . .
C9 C 0.7598(3) 0.65843(9) 0.8971(2) 0.0240(5) Uani 1 1 d . . . . .
H9 H 0.775448 0.628588 0.945612 0.029 Uiso 1 1 calc R U . . .
C20 C -0.0521(3) 0.65479(9) 0.6011(2) 0.0253(5) Uani 1 1 d . . . . .
H20A H -0.080174 0.646001 0.511467 0.038 Uiso 1 1 calc R U . . .
H20B H -0.148245 0.678490 0.610302 0.038 Uiso 1 1 calc R U . . .
H20C H -0.054914 0.624560 0.650245 0.038 Uiso 1 1 calc R U . . .
C7 C 0.8732(3) 0.74015(9) 0.8650(2) 0.0288(5) Uani 1 1 d . . . . .
H7 H 0.967107 0.765678 0.890094 0.035 Uiso 1 1 calc R U . . .
C18 C 0.6673(4) 0.79275(9) 0.6815(2) 0.0333(6) Uani 1 1 d . . . . .
H18A H 0.644617 0.783941 0.592364 0.050 Uiso 1 1 calc R U . . .
H18B H 0.774051 0.816372 0.708843 0.050 Uiso 1 1 calc R U . . .
H18C H 0.552090 0.808186 0.691090 0.050 Uiso 1 1 calc R U . . .
C8 C 0.8953(3) 0.69603(10) 0.9331(2) 0.0309(5) Uani 1 1 d . . . . .
H8 H 1.004703 0.691485 1.005403 0.037 Uiso 1 1 calc R U . . .
B1 B 0.4391(3) 0.62134(8) 0.72557(19) 0.0111(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 Cl2 2.2617(5) . ?
Co1 Cl1 2.2378(5) . ?
Co1 O1 1.9869(13) . ?
Co1 N1 2.0183(16) . ?
O1 C19 1.442(2) . ?
O1 B1 1.520(2) . ?
N1 C1 1.355(2) . ?
N1 C5 1.364(2) . ?
N2 H2 0.8800 . ?
N2 C10 1.349(3) . ?
N2 C6 1.359(3) . ?
C1 C2 1.389(3) . ?
C1 C17 1.497(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.386(3) . ?
C5 C4 1.395(3) . ?
C5 B1 1.630(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C4 H4 0.9500 . ?
C4 C3 1.386(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.395(3) . ?
C12 C13 1.395(3) . ?
C3 H3 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.503(3) . ?
C11 C16 1.405(3) . ?
C11 B1 1.615(3) . ?
C14 H14 0.9500 . ?
C14 C13 1.393(3) . ?
C14 C15 1.379(3) . ?
C10 C9 1.395(3) . ?
C10 B1 1.646(3) . ?
C13 H13 0.9500 . ?
C16 H16 0.9500 . ?
C16 C15 1.394(3) . ?
C15 H15 0.9500 . ?
C6 C7 1.372(3) . ?
C6 C18 1.490(3) . ?
C9 H9 0.9500 . ?
C9 C8 1.385(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C7 H7 0.9500 . ?
C7 C8 1.384(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C8 H8 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Co1 Cl2 112.61(2) . . ?
O1 Co1 Cl2 101.93(4) . . ?
O1 Co1 Cl1 120.22(4) . . ?
O1 Co1 N1 84.77(6) . . ?
N1 Co1 Cl2 117.71(5) . . ?
N1 Co1 Cl1 116.27(5) . . ?
C19 O1 Co1 122.43(11) . . ?
C19 O1 B1 121.04(14) . . ?
B1 O1 Co1 116.03(10) . . ?
C1 N1 Co1 124.34(13) . . ?
C1 N1 C5 121.41(16) . . ?
C5 N1 Co1 114.07(12) . . ?
C10 N2 H2 116.7 . . ?
C10 N2 C6 126.69(19) . . ?
C6 N2 H2 116.7 . . ?
N1 C1 C2 120.30(17) . . ?
N1 C1 C17 116.97(16) . . ?
C2 C1 C17 122.73(17) . . ?
C1 C2 H2A 120.2 . . ?
C3 C2 C1 119.70(18) . . ?
C3 C2 H2A 120.2 . . ?
N1 C5 C4 119.03(17) . . ?
N1 C5 B1 117.57(16) . . ?
C4 C5 B1 123.24(17) . . ?
C1 C17 H17A 109.5 . . ?
C1 C17 H17B 109.5 . . ?
C1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.43(18) . . ?
C3 C4 H4 119.8 . . ?
C11 C12 H12 118.9 . . ?
C11 C12 C13 122.3(2) . . ?
C13 C12 H12 118.9 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.10(18) . . ?
C4 C3 H3 120.5 . . ?
O1 C19 H19A 109.7 . . ?
O1 C19 H19B 109.7 . . ?
O1 C19 C20 109.84(16) . . ?
H19A C19 H19B 108.2 . . ?
C20 C19 H19A 109.7 . . ?
C20 C19 H19B 109.7 . . ?
C12 C11 C16 116.67(18) . . ?
C12 C11 B1 121.56(17) . . ?
C16 C11 B1 121.63(18) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C15 C14 C13 119.48(19) . . ?
N2 C10 C9 115.69(18) . . ?
N2 C10 B1 117.87(16) . . ?
C9 C10 B1 126.17(18) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.6(2) . . ?
C14 C13 H13 120.2 . . ?
C11 C16 H16 119.2 . . ?
C15 C16 C11 121.5(2) . . ?
C15 C16 H16 119.2 . . ?
C14 C15 C16 120.5(2) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
N2 C6 C7 117.1(2) . . ?
N2 C6 C18 117.1(2) . . ?
C7 C6 C18 125.8(2) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 C10 120.1(2) . . ?
C8 C9 H9 119.9 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C6 C7 H7 120.2 . . ?
C6 C7 C8 119.6(2) . . ?
C8 C7 H7 120.2 . . ?
C6 C18 H18A 109.5 . . ?
C6 C18 H18B 109.5 . . ?
C6 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C9 C8 H8 119.6 . . ?
C7 C8 C9 120.8(2) . . ?
C7 C8 H8 119.6 . . ?
O1 B1 C5 105.18(14) . . ?
O1 B1 C11 112.61(15) . . ?
O1 B1 C10 107.24(15) . . ?
C5 B1 C10 104.39(15) . . ?
C11 B1 C5 114.70(16) . . ?
C11 B1 C10 112.02(15) . . ?

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
Co1 O1 C19 C20 74.54(18) . . . . ?
Co1 O1 B1 C5 -14.75(17) . . . . ?
Co1 O1 B1 C11 -140.35(13) . . . . ?
Co1 O1 B1 C10 95.98(14) . . . . ?
Co1 N1 C1 C2 -172.62(13) . . . . ?
Co1 N1 C1 C17 7.9(2) . . . . ?
Co1 N1 C5 C4 173.37(14) . . . . ?
Co1 N1 C5 B1 -11.1(2) . . . . ?
N1 C1 C2 C3 -0.5(3) . . . . ?
N1 C5 C4 C3 0.0(3) . . . . ?
N1 C5 B1 O1 16.6(2) . . . . ?
N1 C5 B1 C11 140.92(17) . . . . ?
N1 C5 B1 C10 -96.11(18) . . . . ?
N2 C10 C9 C8 -0.9(3) . . . . ?
N2 C10 B1 O1 -12.6(2) . . . . ?
N2 C10 B1 C5 98.66(18) . . . . ?
N2 C10 B1 C11 -136.65(17) . . . . ?
N2 C6 C7 C8 -1.9(3) . . . . ?
C1 N1 C5 C4 -1.8(3) . . . . ?
C1 N1 C5 B1 173.70(16) . . . . ?
C1 C2 C3 C4 -1.3(3) . . . . ?
C5 N1 C1 C2 2.1(3) . . . . ?
C5 N1 C1 C17 -177.46(16) . . . . ?
C5 C4 C3 C2 1.5(3) . . . . ?
C17 C1 C2 C3 179.03(18) . . . . ?
C4 C5 B1 O1 -168.04(17) . . . . ?
C4 C5 B1 C11 -43.8(2) . . . . ?
C4 C5 B1 C10 79.2(2) . . . . ?
C12 C11 C16 C15 -0.9(3) . . . . ?
C12 C11 B1 O1 89.7(2) . . . . ?
C12 C11 B1 C5 -30.5(3) . . . . ?
C12 C11 B1 C10 -149.30(18) . . . . ?
C19 O1 B1 C5 173.12(14) . . . . ?
C19 O1 B1 C11 47.5(2) . . . . ?
C19 O1 B1 C10 -76.15(19) . . . . ?
C11 C12 C13 C14 1.9(3) . . . . ?
C11 C16 C15 C14 1.1(3) . . . . ?
C10 N2 C6 C7 2.3(3) . . . . ?
C10 N2 C6 C18 -177.07(19) . . . . ?
C10 C9 C8 C7 1.2(3) . . . . ?
C13 C12 C11 C16 -0.6(3) . . . . ?
C13 C12 C11 B1 -176.39(19) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C16 C11 B1 O1 -85.9(2) . . . . ?
C16 C11 B1 C5 153.87(18) . . . . ?
C16 C11 B1 C10 35.1(2) . . . . ?
C15 C14 C13 C12 -1.7(3) . . . . ?
C6 N2 C10 C9 -0.9(3) . . . . ?
C6 N2 C10 B1 -175.30(17) . . . . ?
C6 C7 C8 C9 0.3(3) . . . . ?
C9 C10 B1 O1 173.61(18) . . . . ?
C9 C10 B1 C5 -75.1(2) . . . . ?
C9 C10 B1 C11 49.6(3) . . . . ?
C18 C6 C7 C8 177.4(2) . . . . ?
B1 O1 C19 C20 -113.85(19) . . . . ?
B1 C5 C4 C3 -175.25(18) . . . . ?
B1 C11 C16 C15 174.87(19) . . . . ?
B1 C10 C9 C8 172.99(19) . . . . ?

_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
;
####################################################################### 
# 
# 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_[NiBr(ToM)]
_database_code_depnum_ccdc_archive 'CCDC 2172878'
loop_
_audit_author_name
_audit_author_address
'Shiro Hikichi'
;Kanagawa University
Japan
;
_audit_update_record             
;
2022-05-16 deposited with the CCDC.	2022-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        Ni(Ph-To)Br
_chemical_name_common            
'[bromo(Phenyltris(oxiazolynyl)borato)nickel(II)]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H29 B Br N3 Ni O3'
_chemical_formula_sum            'C21 H29 B Br N3 Ni O3'
_chemical_formula_weight         520.90
_chemical_compound_source        'synthesis as described'
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'
B B 0.0013 0.0007 '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                   11.0336(5)
_cell_length_b                   13.2310(4)
_cell_length_c                   16.0271(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.895(3)
_cell_angle_gamma                90
_cell_volume                     2327.35(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    6804
_cell_measurement_theta_min      1.8555
_cell_measurement_theta_max      27.4831

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.577
_shelx_estimated_absorpt_T_min   0.425
_shelx_estimated_absorpt_T_max   0.783
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_max  0.7758
_exptl_absorpt_correction_T_min  0.5855
_exptl_absorpt_process_details   
;Numerical (Based on real shape of the crystal) absorption
correction was parformed on CrystalClear (Rigaku Inc., 2007)
with FS_ABSCOR method.
;
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_source_power             3.0000
_diffrn_source_voltage           50.0000
_diffrn_source_current           60.0000
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       
;
Saturn70 (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       ω
_diffrn_reflns_number            5439
_diffrn_number_total             5439
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_sigmaI/detI    0.0610
_diffrn_reflns_theta_full        27.4831
_diffrn_reflns_theta_min         1.8555
_diffrn_reflns_theta_max         27.4831
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_measurement_details      
;
scan:
	Number of images: 600
	           Slice: -110.0000 - 70.0000
	     Image width: 0.3000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 44.8414
	          2theta: -20.1817
scan:
	Number of images: 600
	           Slice: -110.0000 - 70.0000
	     Image width: 0.3000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 44.8414
	          2theta: -20.1817

;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_orient_matrix_UB_11      -0.0014
_diffrn_orient_matrix_UB_12      0.0002
_diffrn_orient_matrix_UB_13      -0.0911
_diffrn_orient_matrix_UB_21      -0.0547
_diffrn_orient_matrix_UB_22      -0.0522
_diffrn_orient_matrix_UB_23      0.0007
_diffrn_orient_matrix_UB_31      -0.0432
_diffrn_orient_matrix_UB_32      0.0451
_diffrn_orient_matrix_UB_33      -0.0056
_diffrn_orient_matrix_type       d*Trek


_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             5213
_reflns_number_gt                4137
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        
'CrystalClear (Rigaku Inc., 2007), SORTAV (Blessing, 1995)'
_computing_structure_solution    'SIR92 (Altomare et al, 1994)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'

_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)+(0.0270P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5213
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0236
_refine_ls_wR_factor_ref         0.0530
_refine_ls_wR_factor_gt          0.0511
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_restrained_S_all      0.978
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.50629(2) 0.25148(2) -0.03764(2) 0.02510(6) Uani 1 1 d . . . . .
Ni1 Ni 0.69349(2) 0.22292(2) 0.03825(2) 0.01364(6) Uani 1 1 d . . . . .
O1 O 0.90857(10) 0.07660(8) 0.22061(6) 0.0141(2) Uani 1 1 d . . . . .
O2 O 1.02944(10) 0.13687(9) -0.02058(7) 0.0210(3) Uani 1 1 d . . . . .
O3 O 0.95640(10) 0.41418(8) 0.13829(7) 0.0190(3) Uani 1 1 d . . . . .
N2 N 0.83160(12) 0.16923(10) -0.01961(8) 0.0152(3) Uani 1 1 d . . . . .
N1 N 0.75166(11) 0.14443(9) 0.14115(8) 0.0134(3) Uani 1 1 d . . . . .
N3 N 0.78459(12) 0.34529(9) 0.07935(8) 0.0138(3) Uani 1 1 d . . . . .
C3 C 0.69672(15) 0.05488(12) 0.17934(10) 0.0153(3) Uani 1 1 d . . . . .
C8 C 0.83682(15) 0.12356(12) -0.10367(9) 0.0178(4) Uani 1 1 d . . . . .
C2 C 0.80153(15) 0.02333(12) 0.24497(10) 0.0168(4) Uani 1 1 d . . . . .
H2A H 0.7841 0.0436 0.3020 0.020 Uiso 1 1 calc R U . . .
H2B H 0.8141 -0.0507 0.2440 0.020 Uiso 1 1 calc R U . . .
C7 C 0.97305(16) 0.09454(13) -0.09932(10) 0.0224(4) Uani 1 1 d . . . . .
H7A H 0.9828 0.0202 -0.0999 0.027 Uiso 1 1 calc R U . . .
H7B H 1.0106 0.1233 -0.1476 0.027 Uiso 1 1 calc R U . . .
C6 C 0.93852(15) 0.17470(11) 0.02079(10) 0.0148(3) Uani 1 1 d . . . . .
C11 C 0.89450(14) 0.33014(11) 0.11020(9) 0.0127(3) Uani 1 1 d . . . . .
C21 C 1.19667(16) 0.24957(12) 0.11521(12) 0.0204(4) Uani 1 1 d . . . . .
H21 H 1.1832 0.2548 0.0559 0.024 Uiso 1 1 calc R U . . .
C19 C 1.33605(16) 0.25717(12) 0.24088(12) 0.0224(4) Uani 1 1 d . . . . .
H19 H 1.4160 0.2669 0.2677 0.027 Uiso 1 1 calc R U . . .
C5 C 0.66970(16) -0.02402(12) 0.11083(10) 0.0226(4) Uani 1 1 d . . . . .
H5A H 0.6334 -0.0838 0.1344 0.034 Uiso 1 1 calc R U . . .
H5B H 0.6127 0.0041 0.0659 0.034 Uiso 1 1 calc R U . . .
H5C H 0.7456 -0.0431 0.0881 0.034 Uiso 1 1 calc R U . . .
C15 C 0.63910(16) 0.47207(13) 0.12211(12) 0.0272(4) Uani 1 1 d . . . . .
H15A H 0.6199 0.5444 0.1216 0.041 Uiso 1 1 calc R U . . .
H15B H 0.5712 0.4348 0.0921 0.041 Uiso 1 1 calc R U . . .
H15C H 0.6521 0.4482 0.1802 0.041 Uiso 1 1 calc R U . . .
C12 C 0.86941(16) 0.49786(12) 0.12951(11) 0.0224(4) Uani 1 1 d . . . . .
H12A H 0.9027 0.5550 0.0991 0.027 Uiso 1 1 calc R U . . .
H12B H 0.8506 0.5219 0.1852 0.027 Uiso 1 1 calc R U . . .
C9 C 0.75250(18) 0.03192(13) -0.11451(11) 0.0273(4) Uani 1 1 d . . . . .
H9A H 0.7568 0.0025 -0.1702 0.041 Uiso 1 1 calc R U . . .
H9B H 0.7780 -0.0185 -0.0715 0.041 Uiso 1 1 calc R U . . .
H9C H 0.6686 0.0530 -0.1088 0.041 Uiso 1 1 calc R U . . .
C16 C 1.09789(14) 0.22702(11) 0.16057(10) 0.0138(3) Uani 1 1 d . . . . .
C17 C 1.12395(15) 0.22089(12) 0.24768(10) 0.0158(3) Uani 1 1 d . . . . .
H17 H 1.0595 0.2062 0.2808 0.019 Uiso 1 1 calc R U . . .
C4 C 0.58158(16) 0.08356(13) 0.21834(11) 0.0265(4) Uani 1 1 d . . . . .
H4A H 0.5475 0.0234 0.2429 0.040 Uiso 1 1 calc R U . . .
H4B H 0.6012 0.1342 0.2622 0.040 Uiso 1 1 calc R U . . .
H4C H 0.5218 0.1115 0.1750 0.040 Uiso 1 1 calc R U . . .
C20 C 1.31359(16) 0.26455(13) 0.15438(12) 0.0244(4) Uani 1 1 d . . . . .
H20 H 1.3784 0.2799 0.1218 0.029 Uiso 1 1 calc R U . . .
C18 C 1.24066(16) 0.23548(11) 0.28764(11) 0.0194(4) Uani 1 1 d . . . . .
H18 H 1.2548 0.2305 0.3470 0.023 Uiso 1 1 calc R U . . .
C1 C 0.86662(14) 0.14687(11) 0.16296(9) 0.0123(3) Uani 1 1 d . . . . .
C10 C 0.80096(18) 0.20362(13) -0.17011(11) 0.0259(4) Uani 1 1 d . . . . .
H10A H 0.8040 0.1744 -0.2260 0.039 Uiso 1 1 calc R U . . .
H10B H 0.7181 0.2273 -0.1643 0.039 Uiso 1 1 calc R U . . .
H10C H 0.8577 0.2607 -0.1627 0.039 Uiso 1 1 calc R U . . .
C13 C 0.75408(15) 0.45469(12) 0.07919(10) 0.0173(4) Uani 1 1 d . . . . .
C14 C 0.73855(18) 0.49288(14) -0.01057(11) 0.0315(5) Uani 1 1 d . . . . .
H14A H 0.7184 0.5650 -0.0109 0.047 Uiso 1 1 calc R U . . .
H14B H 0.8146 0.4828 -0.0362 0.047 Uiso 1 1 calc R U . . .
H14C H 0.6726 0.4555 -0.0426 0.047 Uiso 1 1 calc R U . . .
B1 B 0.96144(17) 0.21976(13) 0.11712(11) 0.0132(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Ni1 2.3178(3) . ?
Ni1 N3 1.9823(13) . ?
Ni1 N2 1.9943(13) . ?
Ni1 N1 1.9983(13) . ?
O1 C1 1.3582(17) . ?
O1 C2 1.4625(18) . ?
O2 C6 1.3541(18) . ?
O2 C7 1.4601(19) . ?
O3 C11 1.3573(17) . ?
O3 C12 1.4627(18) . ?
N2 C6 1.288(2) . ?
N2 C8 1.4829(19) . ?
N1 C1 1.2810(19) . ?
N1 C3 1.4906(19) . ?
N3 C11 1.2776(19) . ?
N3 C13 1.4861(19) . ?
C3 C4 1.521(2) . ?
C3 C5 1.522(2) . ?
C3 C2 1.539(2) . ?
C8 C10 1.525(2) . ?
C8 C9 1.527(2) . ?
C8 C7 1.546(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C6 B1 1.650(2) . ?
C11 B1 1.635(2) . ?
C21 C20 1.390(2) . ?
C21 C16 1.403(2) . ?
C21 H21 0.9500 . ?
C19 C18 1.383(2) . ?
C19 C20 1.386(3) . ?
C19 H19 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C15 C13 1.521(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C12 C13 1.544(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C16 C17 1.399(2) . ?
C16 B1 1.596(2) . ?
C17 C18 1.391(2) . ?
C17 H17 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C20 H20 0.9500 . ?
C18 H18 0.9500 . ?
C1 B1 1.650(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C13 C14 1.518(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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
N3 Ni1 N2 93.43(5) . . ?
N3 Ni1 N1 92.37(5) . . ?
N2 Ni1 N1 90.15(5) . . ?
N3 Ni1 Br1 115.81(4) . . ?
N2 Ni1 Br1 119.76(4) . . ?
N1 Ni1 Br1 135.33(4) . . ?
C1 O1 C2 106.46(12) . . ?
C6 O2 C7 107.08(13) . . ?
C11 O3 C12 106.58(12) . . ?
C6 N2 C8 111.14(13) . . ?
C6 N2 Ni1 116.76(11) . . ?
C8 N2 Ni1 132.10(10) . . ?
C1 N1 C3 109.94(13) . . ?
C1 N1 Ni1 115.92(10) . . ?
C3 N1 Ni1 129.96(10) . . ?
C11 N3 C13 111.06(13) . . ?
C11 N3 Ni1 115.42(10) . . ?
C13 N3 Ni1 133.47(11) . . ?
N1 C3 C4 111.26(13) . . ?
N1 C3 C5 107.87(12) . . ?
C4 C3 C5 110.96(14) . . ?
N1 C3 C2 100.81(12) . . ?
C4 C3 C2 112.80(13) . . ?
C5 C3 C2 112.63(14) . . ?
N2 C8 C10 108.65(13) . . ?
N2 C8 C9 110.29(13) . . ?
C10 C8 C9 111.14(14) . . ?
N2 C8 C7 100.87(12) . . ?
C10 C8 C7 112.66(14) . . ?
C9 C8 C7 112.70(14) . . ?
O1 C2 C3 104.92(12) . . ?
O1 C2 H2A 110.8 . . ?
C3 C2 H2A 110.8 . . ?
O1 C2 H2B 110.8 . . ?
C3 C2 H2B 110.8 . . ?
H2A C2 H2B 108.8 . . ?
O2 C7 C8 105.65(12) . . ?
O2 C7 H7A 110.6 . . ?
C8 C7 H7A 110.6 . . ?
O2 C7 H7B 110.6 . . ?
C8 C7 H7B 110.6 . . ?
H7A C7 H7B 108.7 . . ?
N2 C6 O2 114.79(14) . . ?
N2 C6 B1 122.35(14) . . ?
O2 C6 B1 122.80(14) . . ?
N3 C11 O3 115.16(13) . . ?
N3 C11 B1 124.79(14) . . ?
O3 C11 B1 120.05(13) . . ?
C20 C21 C16 122.05(17) . . ?
C20 C21 H21 119.0 . . ?
C16 C21 H21 119.0 . . ?
C18 C19 C20 119.24(17) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3 C12 C13 105.52(12) . . ?
O3 C12 H12A 110.6 . . ?
C13 C12 H12A 110.6 . . ?
O3 C12 H12B 110.6 . . ?
C13 C12 H12B 110.6 . . ?
H12A C12 H12B 108.8 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C17 C16 C21 116.02(16) . . ?
C17 C16 B1 121.35(14) . . ?
C21 C16 B1 122.35(15) . . ?
C18 C17 C16 122.48(16) . . ?
C18 C17 H17 118.8 . . ?
C16 C17 H17 118.8 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C19 C20 C21 120.27(17) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C19 C18 C17 119.94(16) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
N1 C1 O1 115.28(13) . . ?
N1 C1 B1 123.27(14) . . ?
O1 C1 B1 121.05(13) . . ?
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 . . ?
N3 C13 C14 109.23(13) . . ?
N3 C13 C15 110.22(13) . . ?
C14 C13 C15 111.10(15) . . ?
N3 C13 C12 100.66(12) . . ?
C14 C13 C12 112.24(14) . . ?
C15 C13 C12 112.87(14) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 B1 C11 112.04(13) . . ?
C16 B1 C1 117.00(13) . . ?
C11 B1 C1 104.46(12) . . ?
C16 B1 C6 118.50(14) . . ?
C11 B1 C6 103.56(12) . . ?
C1 B1 C6 99.33(12) . . ?

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
C1 N1 C3 C4 133.55(14) . . . . ?
Ni1 N1 C3 C4 -70.85(17) . . . . ?
C1 N1 C3 C5 -104.53(15) . . . . ?
Ni1 N1 C3 C5 51.07(17) . . . . ?
C1 N1 C3 C2 13.70(16) . . . . ?
Ni1 N1 C3 C2 169.31(10) . . . . ?
C6 N2 C8 C10 -113.70(16) . . . . ?
Ni1 N2 C8 C10 65.37(18) . . . . ?
C6 N2 C8 C9 124.26(15) . . . . ?
Ni1 N2 C8 C9 -56.68(18) . . . . ?
C6 N2 C8 C7 4.92(16) . . . . ?
Ni1 N2 C8 C7 -176.02(11) . . . . ?
C1 O1 C2 C3 12.87(15) . . . . ?
N1 C3 C2 O1 -15.51(14) . . . . ?
C4 C3 C2 O1 -134.25(13) . . . . ?
C5 C3 C2 O1 99.20(14) . . . . ?
C6 O2 C7 C8 6.38(16) . . . . ?
N2 C8 C7 O2 -6.61(15) . . . . ?
C10 C8 C7 O2 109.05(15) . . . . ?
C9 C8 C7 O2 -124.20(14) . . . . ?
C8 N2 C6 O2 -1.14(18) . . . . ?
Ni1 N2 C6 O2 179.63(10) . . . . ?
C8 N2 C6 B1 -178.56(13) . . . . ?
Ni1 N2 C6 B1 2.22(19) . . . . ?
C7 O2 C6 N2 -3.54(17) . . . . ?
C7 O2 C6 B1 173.86(13) . . . . ?
C13 N3 C11 O3 2.35(18) . . . . ?
Ni1 N3 C11 O3 -179.96(9) . . . . ?
C13 N3 C11 B1 -177.55(13) . . . . ?
Ni1 N3 C11 B1 0.15(19) . . . . ?
C12 O3 C11 N3 4.53(17) . . . . ?
C12 O3 C11 B1 -175.57(13) . . . . ?
C11 O3 C12 C13 -9.00(16) . . . . ?
C20 C21 C16 C17 0.2(2) . . . . ?
C20 C21 C16 B1 174.22(15) . . . . ?
C21 C16 C17 C18 -0.4(2) . . . . ?
B1 C16 C17 C18 -174.45(14) . . . . ?
C18 C19 C20 C21 -0.5(2) . . . . ?
C16 C21 C20 C19 0.2(3) . . . . ?
C20 C19 C18 C17 0.3(2) . . . . ?
C16 C17 C18 C19 0.1(2) . . . . ?
C3 N1 C1 O1 -6.50(18) . . . . ?
Ni1 N1 C1 O1 -165.89(9) . . . . ?
C3 N1 C1 B1 166.28(13) . . . . ?
Ni1 N1 C1 B1 6.89(19) . . . . ?
C2 O1 C1 N1 -4.48(17) . . . . ?
C2 O1 C1 B1 -177.44(13) . . . . ?
C11 N3 C13 C14 110.67(16) . . . . ?
Ni1 N3 C13 C14 -66.46(18) . . . . ?
C11 N3 C13 C15 -127.00(15) . . . . ?
Ni1 N3 C13 C15 55.87(18) . . . . ?
C11 N3 C13 C12 -7.60(17) . . . . ?
Ni1 N3 C13 C12 175.27(11) . . . . ?
O3 C12 C13 N3 9.70(16) . . . . ?
O3 C12 C13 C14 -106.35(15) . . . . ?
O3 C12 C13 C15 127.16(14) . . . . ?
C17 C16 B1 C11 87.79(17) . . . . ?
C21 C16 B1 C11 -85.87(18) . . . . ?
C17 C16 B1 C1 -32.8(2) . . . . ?
C21 C16 B1 C1 153.56(14) . . . . ?
C17 C16 B1 C6 -151.70(14) . . . . ?
C21 C16 B1 C6 34.6(2) . . . . ?
N3 C11 B1 C16 -178.78(14) . . . . ?
O3 C11 B1 C16 1.33(19) . . . . ?
N3 C11 B1 C1 -51.18(18) . . . . ?
O3 C11 B1 C1 128.93(14) . . . . ?
N3 C11 B1 C6 52.37(19) . . . . ?
O3 C11 B1 C6 -127.52(14) . . . . ?
N1 C1 B1 C16 170.66(14) . . . . ?
O1 C1 B1 C16 -17.0(2) . . . . ?
N1 C1 B1 C11 46.17(19) . . . . ?
O1 C1 B1 C11 -141.45(13) . . . . ?
N1 C1 B1 C6 -60.55(18) . . . . ?
O1 C1 B1 C6 111.83(14) . . . . ?
N2 C6 B1 C16 -177.85(14) . . . . ?
O2 C6 B1 C16 4.9(2) . . . . ?
N2 C6 B1 C11 -53.08(18) . . . . ?
O2 C6 B1 C11 129.71(14) . . . . ?
N2 C6 B1 C1 54.37(18) . . . . ?
O2 C6 B1 C1 -122.83(14) . . . . ?

_refine_diff_density_max         0.728
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.059



####################################################################### 
# 
# 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_[NiBr(TpyMe)]
_database_code_depnum_ccdc_archive 'CCDC 2172877'
loop_
_audit_author_name
_audit_author_address
'Shiro Hikichi'
;Kanagawa University
Japan
;
_audit_update_record             
;
2022-05-16 deposited with the CCDC.	2022-05-30 downloaded from the CCDC.
;
_audit_creation_date             2022-05-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H23 B Br N3 Ni'
_chemical_formula_sum            'C24 H23 B Br N3 Ni'
_chemical_formula_weight         502.88
_chemical_melting_point          ?
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'
B B 0.0090 0.0039 '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'
N N 0.0311 0.0180 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.9893(2)
_cell_length_b                   15.9480(3)
_cell_length_c                   13.6069(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.906(2)
_cell_angle_gamma                90
_cell_volume                     2166.51(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    26442
_cell_measurement_temperature    90
_cell_measurement_theta_max      76.0760
_cell_measurement_theta_min      4.2400
_shelx_estimated_absorpt_T_max   0.702
_shelx_estimated_absorpt_T_min   0.477
_exptl_absorpt_coefficient_mu    3.562
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87236
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.114a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.107
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            32868
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.124
_diffrn_reflns_theta_min         4.272
_diffrn_ambient_temperature      90.00
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     31.00 119.00   0.50    0.05    --   46.17  57.00  30.00  176
  2  ω     41.00  67.00   0.50    0.05    --   46.17  47.00-125.00   52
  3  ω     69.00 109.00   0.50    0.05    --   46.17  47.00-125.00   80
  4  ω    -12.00  14.00   0.50    0.05    --  -46.17  19.00  30.00   52
  5  ω     -8.00  29.00   0.50    0.05    --  -46.17  19.00   0.00   74
  6  ω    -18.00  28.00   0.50    0.05    --  -46.17  19.00 -30.00   92
  7  ω    -36.00 -11.00   0.50    0.05    --  -46.17  47.00-125.00   50
  8  ω     35.00  68.00   0.50    0.05    --  104.15 -61.00-150.00   66
  9  ω     36.00  71.00   0.50    0.05    --  104.15 -61.00 -90.00   70
 10  ω     39.00  74.00   0.50    0.05    --  104.15 -61.00 -60.00   70
 11  ω     42.00  67.00   0.50    0.05    --  104.15 -61.00 -30.00   50
 12  ω    -11.00  52.00   0.50    0.05    --   46.17 -47.00  85.00  126
 13  ω     32.00  79.00   0.50    0.05    --  104.15 -94.00 -90.00   94
 14  ω     21.00  93.00   0.50    0.05    --   46.17-125.00-150.00  144
 15  ω     37.00  74.00   0.50    0.05    --  104.15-125.00  30.00   74
 16  ω     94.00 120.00   0.50    0.05    --  104.15  47.00-125.00   52
 17  ω     84.00 110.00   0.50    0.05    --  104.15  77.00 -30.00   52
 18  ω    131.00 171.00   0.50    0.05    --  104.15  77.00 -30.00   80
 19  ω    108.00 175.00   0.50    0.05    --  104.15  45.00  30.00  134
 20  ω    125.00 171.00   0.50    0.05    --  104.15  61.00 150.00   92
 21  ω     89.00 115.00   0.50    0.05    --  104.15  61.00 150.00   52
 22  ω    -70.00 -31.00   0.50    0.05    -- -102.00  61.00-120.00   78
 23  ω    -66.00 -30.00   0.50    0.05    -- -102.00  61.00  60.00   72
 24  ω    -70.00 -38.00   0.50    0.05    -- -102.00  61.00  90.00   64
 25  ω    -69.00 -32.00   0.50    0.05    -- -102.00  61.00 120.00   74
 26  ω   -170.00-144.00   0.50    0.05    -- -102.00 -83.00  22.07   52
 27  ω   -175.00-128.00   0.50    0.05    -- -102.00 -77.00 -30.00   94
 28  ω   -105.00 -80.00   0.50    0.05    -- -102.00 -83.00  22.07   50
 29  ω   -109.00 -80.00   0.50    0.05    -- -102.00 -77.00  60.00   58
 30  ω   -104.00 -79.00   0.50    0.05    -- -102.00 -77.00  30.00   50
 31  ω   -107.00 -82.00   0.50    0.05    -- -102.00 -77.00   0.00   50
 32  ω   -105.00 -80.00   0.50    0.05    -- -102.00 -81.00 -16.54   50
 33  ω   -108.00 -80.00   0.50    0.05    -- -102.00 -77.00 -30.00   56
 34  ω   -175.00-132.00   0.50    0.05    -- -102.00 -77.00  30.00   86
 35  ω   -171.00-135.00   0.50    0.05    -- -102.00 -77.00   0.00   72
 36  ω   -121.00 -85.00   0.50    0.05    -- -102.00 -61.00  30.00   72
 37  ω    -92.00 -31.00   0.50    0.05    --  -46.17 -57.00   0.00  122
 38  ω   -108.00 -82.00   0.50    0.05    -- -102.00 -69.00 -22.44   52
 39  ω   -118.00 -87.00   0.50    0.05    -- -102.00 -59.00  11.77   62
 40  ω   -174.00 -85.00   0.50    0.05    -- -102.00 -61.00   0.00  178
 41  ω   -162.00 -87.00   0.50    0.05    -- -102.00 -57.00 -51.00  150
 42  ω   -113.00 -88.00   0.50    0.05    -- -102.00 -56.00 -45.49   50
 43  ω   -119.00 -93.00   0.50    0.05    -- -102.00 -49.00 -35.06   52
 44  ω   -155.00 -89.00   0.50    0.05    -- -102.00 -49.00 -30.98  132
 45  ω   -138.00 -87.00   0.50    0.05    -- -102.00 -55.00  14.03  102
 46  ω   -131.00 -92.00   0.50    0.05    -- -102.00 -47.00  85.00   78
 47  ω   -172.00 -91.00   0.50    0.05    -- -102.00 -45.00 150.00  162
 48  ω    -87.00 -61.00   0.50    0.05    --  -46.17 -47.00  85.00   52
 49  ω   -116.00 -91.00   0.50    0.05    -- -102.00 -53.00 -19.95   50
 50  ω   -164.00-105.00   0.50    0.05    -- -102.00 -45.00 -90.00  118
 51  ω   -172.00 -85.00   0.50    0.05    -- -102.00 -61.00-180.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4290
_reflns_number_total             4406
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.114a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.114a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.114a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.933
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4406
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0268
_refine_ls_restrained_S_all      1.052
_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)+(0.0307P)²+2.1093P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0679
_refine_ls_wR_factor_ref         0.0682
_refine_special_details          ?
_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 Aromatic/amide H refined with riding coordinates:
 C13(H13), C12(H12), C14(H14), C4(H4), C2(H2), C20(H20), C9(H9), C18(H18),
 C19(H19), C3(H3), C8(H8), C7(H7)
2.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
Br1 Br 0.22298(2) 0.58051(2) 0.01067(2) 0.02859(7) Uani 1 1 d . . . . .
Ni1 Ni 0.23243(3) 0.56645(2) 0.18365(2) 0.01840(8) Uani 1 1 d . . . . .
N3 N 0.22232(14) 0.46555(9) 0.26616(10) 0.0186(3) Uani 1 1 d . . . . .
N1 N 0.10039(14) 0.63307(9) 0.26253(10) 0.0178(3) Uani 1 1 d . . . . .
N2 N 0.40129(15) 0.60690(10) 0.25691(10) 0.0216(3) Uani 1 1 d . . . . .
C10 C 0.38556(17) 0.61972(11) 0.35503(12) 0.0205(3) Uani 1 1 d . . . . .
C5 C 0.13436(17) 0.63840(11) 0.36036(12) 0.0193(3) Uani 1 1 d . . . . .
C16 C 0.26004(18) 0.57340(11) 0.52430(13) 0.0204(3) Uani 1 1 d . . . . .
C11 C 0.20795(18) 0.38670(11) 0.22949(13) 0.0225(4) Uani 1 1 d . . . . .
C13 C 0.22388(18) 0.33026(12) 0.39159(14) 0.0243(4) Uani 1 1 d . . . . .
H13 H 0.225482 0.283634 0.435069 0.029 Uiso 1 1 calc R U . . .
C21 C 0.37900(18) 0.56327(12) 0.58091(13) 0.0223(4) Uani 1 1 d . . . . .
H21 H 0.463(2) 0.5624(14) 0.5509(17) 0.027 Uiso 1 1 d . U . . .
C15 C 0.23627(16) 0.48020(11) 0.36502(12) 0.0179(3) Uani 1 1 d . . . . .
C25 C 0.00195(17) 0.68243(11) 0.22193(13) 0.0215(3) Uani 1 1 d . . . . .
C17 C 0.14095(19) 0.56704(13) 0.57640(14) 0.0258(4) Uani 1 1 d . . . . .
H17 H 0.059(3) 0.5703(14) 0.5446(18) 0.031 Uiso 1 1 d . U . . .
C12 C 0.20890(19) 0.31810(12) 0.29112(14) 0.0252(4) Uani 1 1 d . . . . .
H12 H 0.199389 0.263116 0.264933 0.030 Uiso 1 1 calc R U . . .
C14 C 0.23648(18) 0.41087(11) 0.42810(13) 0.0217(3) Uani 1 1 d . . . . .
H14 H 0.245417 0.419345 0.497111 0.026 Uiso 1 1 calc R U . . .
C4 C 0.07525(19) 0.70131(12) 0.41609(14) 0.0265(4) Uani 1 1 d . . . . .
H4 H 0.099239 0.706590 0.483950 0.032 Uiso 1 1 calc R U . . .
C2 C -0.05646(18) 0.74526(11) 0.27645(15) 0.0266(4) Uani 1 1 d . . . . .
H2 H -0.122806 0.780712 0.246926 0.032 Uiso 1 1 calc R U . . .
C20 C 0.3801(2) 0.55087(12) 0.68206(13) 0.0266(4) Uani 1 1 d . . . . .
H20 H 0.463012 0.545292 0.717717 0.032 Uiso 1 1 calc R U . . .
C9 C 0.47568(19) 0.67233(13) 0.40591(13) 0.0267(4) Uani 1 1 d . . . . .
H9 H 0.463080 0.684094 0.473417 0.032 Uiso 1 1 calc R U . . .
C18 C 0.1409(2) 0.55411(14) 0.67736(15) 0.0322(4) Uani 1 1 d . . . . .
H18 H 0.058285 0.550382 0.709743 0.039 Uiso 1 1 calc R U . . .
C6 C 0.51229(19) 0.63508(15) 0.21268(14) 0.0307(4) Uani 1 1 d . . . . .
C19 C 0.2609(2) 0.54659(14) 0.73124(13) 0.0309(4) Uani 1 1 d . . . . .
H19 H 0.261238 0.538674 0.800443 0.037 Uiso 1 1 calc R U . . .
C24 C 0.1900(2) 0.37722(13) 0.11998(14) 0.0334(5) Uani 1 1 d . . . . .
H24A H 0.107303 0.405379 0.097607 0.050 Uiso 1 1 calc R U . . .
H24B H 0.184637 0.317538 0.103147 0.050 Uiso 1 1 calc R U . . .
H24C H 0.266434 0.402551 0.087749 0.050 Uiso 1 1 calc R U . . .
C22 C -0.0454(2) 0.66764(13) 0.11781(14) 0.0290(4) Uani 1 1 d . . . . .
H22A H 0.024121 0.685423 0.073131 0.044 Uiso 1 1 calc R U . . .
H22B H -0.127294 0.700001 0.104048 0.044 Uiso 1 1 calc R U . . .
H22C H -0.064019 0.607828 0.108113 0.044 Uiso 1 1 calc R U . . .
C3 C -0.0176(2) 0.75588(12) 0.37378(16) 0.0304(4) Uani 1 1 d . . . . .
H3 H -0.053983 0.800092 0.411302 0.036 Uiso 1 1 calc R U . . .
C8 C 0.5831(2) 0.70753(16) 0.35916(15) 0.0394(5) Uani 1 1 d . . . . .
H8 H 0.641509 0.745666 0.392868 0.047 Uiso 1 1 calc R U . . .
B1 B 0.25397(19) 0.57739(12) 0.40452(14) 0.0182(4) Uani 1 1 d . . . . .
C7 C 0.6036(2) 0.68605(18) 0.26254(16) 0.0425(6) Uani 1 1 d . . . . .
H7 H 0.680227 0.706215 0.230403 0.051 Uiso 1 1 calc R U . . .
C23 C 0.5382(2) 0.60840(19) 0.10923(15) 0.0429(6) Uani 1 1 d . . . . .
H23A H 0.514309 0.549162 0.100872 0.064 Uiso 1 1 calc R U . . .
H23B H 0.633233 0.616126 0.096109 0.064 Uiso 1 1 calc R U . . .
H23C H 0.483810 0.642497 0.063185 0.064 Uiso 1 1 calc R 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
Br1 Ni1 2.3631(3) . ?
Ni1 N3 1.9666(15) . ?
Ni1 N1 2.0285(14) . ?
Ni1 N2 2.0355(15) . ?
N3 C11 1.359(2) . ?
N3 C15 1.368(2) . ?
N1 C5 1.365(2) . ?
N1 C25 1.362(2) . ?
N2 C10 1.365(2) . ?
N2 C6 1.356(2) . ?
C10 C9 1.397(2) . ?
C10 B1 1.642(3) . ?
C5 C4 1.400(2) . ?
C5 B1 1.639(3) . ?
C16 C21 1.404(3) . ?
C16 C17 1.409(3) . ?
C16 B1 1.630(2) . ?
C11 C12 1.378(3) . ?
C11 C24 1.503(2) . ?
C13 H13 0.9500 . ?
C13 C12 1.384(3) . ?
C13 C14 1.383(3) . ?
C21 H21 0.95(2) . ?
C21 C20 1.390(3) . ?
C15 C14 1.400(3) . ?
C15 B1 1.648(2) . ?
C25 C2 1.387(3) . ?
C25 C22 1.497(3) . ?
C17 H17 0.92(3) . ?
C17 C18 1.389(3) . ?
C12 H12 0.9500 . ?
C14 H14 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.383(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.378(3) . ?
C20 H20 0.9500 . ?
C20 C19 1.387(3) . ?
C9 H9 0.9500 . ?
C9 C8 1.385(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.389(3) . ?
C6 C7 1.383(3) . ?
C6 C23 1.501(3) . ?
C19 H19 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C3 H3 0.9500 . ?
C8 H8 0.9500 . ?
C8 C7 1.380(3) . ?
C7 H7 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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
N3 Ni1 Br1 130.18(4) . . ?
N3 Ni1 N1 94.58(6) . . ?
N3 Ni1 N2 92.13(6) . . ?
N1 Ni1 Br1 118.18(4) . . ?
N1 Ni1 N2 96.76(6) . . ?
N2 Ni1 Br1 117.56(4) . . ?
C11 N3 Ni1 123.67(12) . . ?
C11 N3 C15 121.69(15) . . ?
C15 N3 Ni1 114.60(11) . . ?
C5 N1 Ni1 113.81(11) . . ?
C25 N1 Ni1 124.15(12) . . ?
C25 N1 C5 120.80(15) . . ?
C10 N2 Ni1 113.95(11) . . ?
C6 N2 Ni1 124.36(12) . . ?
C6 N2 C10 120.46(15) . . ?
N2 C10 C9 118.78(16) . . ?
N2 C10 B1 117.35(14) . . ?
C9 C10 B1 123.72(15) . . ?
N1 C5 C4 118.50(16) . . ?
N1 C5 B1 118.35(14) . . ?
C4 C5 B1 122.83(15) . . ?
C21 C16 C17 115.41(17) . . ?
C21 C16 B1 123.77(15) . . ?
C17 C16 B1 120.14(16) . . ?
N3 C11 C12 120.84(16) . . ?
N3 C11 C24 117.72(17) . . ?
C12 C11 C24 121.44(16) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C14 C13 C12 119.39(17) . . ?
C16 C21 H21 120.8(14) . . ?
C20 C21 C16 122.57(17) . . ?
C20 C21 H21 116.5(14) . . ?
N3 C15 C14 117.79(15) . . ?
N3 C15 B1 119.19(15) . . ?
C14 C15 B1 123.02(15) . . ?
N1 C25 C2 120.76(17) . . ?
N1 C25 C22 119.59(16) . . ?
C2 C25 C22 119.65(17) . . ?
C16 C17 H17 121.1(15) . . ?
C18 C17 C16 122.46(18) . . ?
C18 C17 H17 116.4(15) . . ?
C11 C12 C13 119.21(17) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C13 C14 C15 121.06(16) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C5 C4 H4 119.5 . . ?
C3 C4 C5 120.96(18) . . ?
C3 C4 H4 119.5 . . ?
C25 C2 H2 120.2 . . ?
C3 C2 C25 119.51(18) . . ?
C3 C2 H2 120.2 . . ?
C21 C20 H20 119.8 . . ?
C19 C20 C21 120.39(18) . . ?
C19 C20 H20 119.8 . . ?
C10 C9 H9 119.6 . . ?
C8 C9 C10 120.82(18) . . ?
C8 C9 H9 119.6 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.38(18) . . ?
C19 C18 H18 119.8 . . ?
N2 C6 C7 120.87(18) . . ?
N2 C6 C23 119.41(18) . . ?
C7 C6 C23 119.69(18) . . ?
C20 C19 C18 118.74(17) . . ?
C20 C19 H19 120.6 . . ?
C18 C19 H19 120.6 . . ?
C11 C24 H24A 109.5 . . ?
C11 C24 H24B 109.5 . . ?
C11 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C25 C22 H22A 109.5 . . ?
C25 C22 H22B 109.5 . . ?
C25 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C4 C3 H3 120.5 . . ?
C2 C3 C4 119.10(17) . . ?
C2 C3 H3 120.5 . . ?
C9 C8 H8 120.7 . . ?
C7 C8 C9 118.60(19) . . ?
C7 C8 H8 120.7 . . ?
C10 B1 C15 109.37(13) . . ?
C5 B1 C10 100.91(14) . . ?
C5 B1 C15 111.69(13) . . ?
C16 B1 C10 114.99(14) . . ?
C16 B1 C5 113.08(14) . . ?
C16 B1 C15 106.82(14) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.79(19) . . ?
C8 C7 H7 120.1 . . ?
C6 C23 H23A 109.5 . . ?
C6 C23 H23B 109.5 . . ?
C6 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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 N3 C11 C12 176.40(13) . . . . ?
Ni1 N3 C11 C24 -4.1(2) . . . . ?
Ni1 N3 C15 C14 -177.05(12) . . . . ?
Ni1 N3 C15 B1 2.14(18) . . . . ?
Ni1 N1 C5 C4 161.55(13) . . . . ?
Ni1 N1 C5 B1 -12.09(18) . . . . ?
Ni1 N1 C25 C2 -159.67(13) . . . . ?
Ni1 N1 C25 C22 21.4(2) . . . . ?
Ni1 N2 C10 C9 -158.90(14) . . . . ?
Ni1 N2 C10 B1 16.7(2) . . . . ?
Ni1 N2 C6 C7 158.54(18) . . . . ?
Ni1 N2 C6 C23 -23.3(3) . . . . ?
N3 C11 C12 C13 0.4(3) . . . . ?
N3 C15 C14 C13 0.4(3) . . . . ?
N3 C15 B1 C10 -57.87(19) . . . . ?
N3 C15 B1 C5 52.98(19) . . . . ?
N3 C15 B1 C16 177.10(14) . . . . ?
N1 C5 C4 C3 1.3(3) . . . . ?
N1 C5 B1 C10 70.55(17) . . . . ?
N1 C5 B1 C16 -166.09(14) . . . . ?
N1 C5 B1 C15 -45.6(2) . . . . ?
N1 C25 C2 C3 -2.2(3) . . . . ?
N2 C10 C9 C8 -3.3(3) . . . . ?
N2 C10 B1 C5 -73.32(18) . . . . ?
N2 C10 B1 C16 164.65(15) . . . . ?
N2 C10 B1 C15 44.5(2) . . . . ?
N2 C6 C7 C8 1.1(4) . . . . ?
C10 N2 C6 C7 -8.0(3) . . . . ?
C10 N2 C6 C23 170.13(19) . . . . ?
C10 C9 C8 C7 -3.4(4) . . . . ?
C5 N1 C25 C2 6.8(2) . . . . ?
C5 N1 C25 C22 -172.12(16) . . . . ?
C5 C4 C3 C2 3.1(3) . . . . ?
C16 C21 C20 C19 1.1(3) . . . . ?
C16 C17 C18 C19 -0.2(3) . . . . ?
C11 N3 C15 C14 0.5(2) . . . . ?
C11 N3 C15 B1 179.73(15) . . . . ?
C21 C16 C17 C18 1.8(3) . . . . ?
C21 C16 B1 C10 -32.3(2) . . . . ?
C21 C16 B1 C5 -147.48(17) . . . . ?
C21 C16 B1 C15 89.26(19) . . . . ?
C21 C20 C19 C18 0.6(3) . . . . ?
C15 N3 C11 C12 -1.0(3) . . . . ?
C15 N3 C11 C24 178.58(16) . . . . ?
C25 N1 C5 C4 -6.2(2) . . . . ?
C25 N1 C5 B1 -179.84(15) . . . . ?
C25 C2 C3 C4 -2.6(3) . . . . ?
C17 C16 C21 C20 -2.3(3) . . . . ?
C17 C16 B1 C10 157.64(16) . . . . ?
C17 C16 B1 C5 42.4(2) . . . . ?
C17 C16 B1 C15 -80.8(2) . . . . ?
C17 C18 C19 C20 -1.1(3) . . . . ?
C12 C13 C14 C15 -0.9(3) . . . . ?
C14 C13 C12 C11 0.5(3) . . . . ?
C14 C15 B1 C10 121.28(17) . . . . ?
C14 C15 B1 C5 -127.88(17) . . . . ?
C14 C15 B1 C16 -3.8(2) . . . . ?
C4 C5 B1 C10 -102.79(18) . . . . ?
C4 C5 B1 C16 20.6(2) . . . . ?
C4 C5 B1 C15 141.09(17) . . . . ?
C9 C10 B1 C5 102.01(19) . . . . ?
C9 C10 B1 C16 -20.0(3) . . . . ?
C9 C10 B1 C15 -140.17(18) . . . . ?
C9 C8 C7 C6 4.5(4) . . . . ?
C6 N2 C10 C9 9.0(3) . . . . ?
C6 N2 C10 B1 -175.43(17) . . . . ?
C24 C11 C12 C13 -179.10(18) . . . . ?
C22 C25 C2 C3 176.65(18) . . . . ?
B1 C10 C9 C8 -178.5(2) . . . . ?
B1 C5 C4 C3 174.64(17) . . . . ?
B1 C16 C21 C20 -172.77(17) . . . . ?
B1 C16 C17 C18 172.70(18) . . . . ?
B1 C15 C14 C13 -178.74(16) . . . . ?
C23 C6 C7 C8 -177.1(2) . . . . ?

_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
;
