# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_hadi0811
_database_code_depnum_ccdc_archive 'CCDC 2000643'
loop_
_audit_author_name
_audit_author_address
'Olivier Blacque'
;University of Zurich
Switzerland
;
_audit_update_record             
;
2020-05-02 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
;

_audit_creation_date             2019-11-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H24 Br4 N2 Ni O2'
_chemical_formula_sum            'C30 H24 Br4 N2 Ni O2'
_chemical_formula_weight         822.86
_chemical_absolute_configuration ad
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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           5
_space_group_name_H-M_alt        'I 1 2 1'
_space_group_name_Hall           'I 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   10.1024(2)
_cell_length_b                   10.91929(18)
_cell_length_c                   13.0659(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.645(2)
_cell_angle_gamma                90
_cell_volume                     1380.91(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8031
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      29.0030
_cell_measurement_theta_min      3.2400
_shelx_estimated_absorpt_T_max   0.828
_shelx_estimated_absorpt_T_min   0.292
_exptl_absorpt_coefficient_mu    6.522
_exptl_absorpt_correction_T_max  0.833
_exptl_absorpt_correction_T_min  0.411
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.979
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             804
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -1 0.0256
-1 0 1 0.0036
1 -5 -2 0.0638
0 1 5 0.0862
-1 3 -5 0.0769
-1 5 -2 0.0823
1 -5 0 0.0815
5 3 0 0.0778

_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.03

_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13776
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.812
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -22.00  85.10   0.70   30.00    --   10.31  77.00 120.00  153
  2  ω    -22.00  85.10   0.70   30.00    --   10.31  77.00-120.00  153
  3  ω    -85.00  13.00   0.70   30.00    --  -10.94 -38.00 -88.00  140
  4  ω    -44.00  64.50   0.70   30.00    --  -10.94  77.00   0.00  155
  5  ω    -20.00  50.00   0.70   30.00    --   10.31 -99.00-150.00  100
  6  ω     34.00  96.30   0.70   30.00    --   10.31-178.00-150.00   89
  7  ω     35.00  98.00   0.70   30.00    --   10.31 178.00   0.00   90
  8  ω    -20.00  50.00   0.70   30.00    --   10.31 -99.00 -60.00  100
  9  ω    -85.00  13.00   0.70   30.00    --  -10.94 -37.00   0.00  140
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0308466000
_diffrn_orient_matrix_UB_12      0.0537948000
_diffrn_orient_matrix_UB_13      -0.0269343000
_diffrn_orient_matrix_UB_21      -0.0648222000
_diffrn_orient_matrix_UB_22      -0.0185231000
_diffrn_orient_matrix_UB_23      0.0056843000
_diffrn_orient_matrix_UB_31      0.0147039000
_diffrn_orient_matrix_UB_32      0.0313287000
_diffrn_orient_matrix_UB_33      0.0495425000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.898
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2747
_reflns_number_total             2849

_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015b)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_refine_diff_density_max         1.464
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.109
_refine_ls_abs_structure_details 
;
 Flack x determined using 1243 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2849
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0335
_refine_ls_restrained_S_all      1.028
_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)+(0.0600P)²+1.1452P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0856
_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 Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.55439(6) 0.77455(5) 0.16983(5) 0.02491(18) Uani 1 1 d . . . . .
Br2 Br 0.16801(7) 0.41892(6) -0.04940(5) 0.0302(2) Uani 1 1 d . . . . .
C1 C 0.3995(6) 0.6232(5) 0.2705(5) 0.0179(11) Uani 1 1 d . . . . .
C2 C 0.4163(6) 0.6558(6) 0.1707(5) 0.0198(13) Uani 1 1 d . . . . .
C3 C 0.3472(6) 0.5999(6) 0.0754(5) 0.0217(13) Uani 1 1 d . . . . .
H3 H 0.361690 0.624992 0.009813 0.026 Uiso 1 1 calc R . . . .
C4 C 0.2556(6) 0.5055(6) 0.0787(5) 0.0235(13) Uani 1 1 d . . . . .
C5 C 0.2316(6) 0.4710(6) 0.1721(5) 0.0212(12) Uani 1 1 d . . . . .
H5 H 0.167018 0.407804 0.172123 0.025 Uiso 1 1 calc R . . . .
C6 C 0.3023(6) 0.5288(6) 0.2682(5) 0.0189(12) Uani 1 1 d . . . . .
C7 C 0.2661(6) 0.4916(6) 0.3637(5) 0.0201(12) Uani 1 1 d . . . . .
H7 H 0.190083 0.437103 0.352968 0.024 Uiso 1 1 calc R . . . .
C8 C 0.2528(6) 0.4830(6) 0.5389(5) 0.0219(12) Uani 1 1 d . . . . .
H8 H 0.172596 0.431204 0.499732 0.026 Uiso 1 1 calc R . . . .
C9 C 0.3471(6) 0.4027(6) 0.6255(5) 0.0202(12) Uani 1 1 d . . . . .
C10 C 0.4082(7) 0.3021(6) 0.5918(6) 0.0271(15) Uani 1 1 d . . . . .
H10 H 0.391402 0.286125 0.517657 0.032 Uiso 1 1 calc R . . . .
C11 C 0.4941(8) 0.2248(7) 0.6669(6) 0.0344(16) Uani 1 1 d . . . . .
H11 H 0.538046 0.157543 0.644078 0.041 Uiso 1 1 calc R . . . .
C12 C 0.5154(8) 0.2461(7) 0.7753(6) 0.0336(16) Uani 1 1 d . . . . .
H12 H 0.573545 0.193108 0.826546 0.040 Uiso 1 1 calc R . . . .
C13 C 0.4523(7) 0.3443(7) 0.8086(5) 0.0285(15) Uani 1 1 d . . . . .
H13 H 0.466094 0.358014 0.882690 0.034 Uiso 1 1 calc R . . . .
C14 C 0.3686(6) 0.4233(6) 0.7342(5) 0.0233(12) Uani 1 1 d . . . . .
H14 H 0.326071 0.491259 0.757530 0.028 Uiso 1 1 calc R . . . .
C15 C 0.1944(7) 0.5936(6) 0.5829(5) 0.0262(14) Uani 1 1 d . . . . .
H15A H 0.270292 0.647326 0.620896 0.039 Uiso 1 1 calc GR . . . .
H15B H 0.143608 0.565776 0.632209 0.039 Uiso 1 1 calc GR . . . .
H15C H 0.131734 0.638819 0.523757 0.039 Uiso 1 1 calc GR . . . .
N1 N 0.3241(5) 0.5232(5) 0.4600(4) 0.0210(11) Uani 1 1 d . . . . .
Ni1 Ni 0.500000 0.62194(10) 0.500000 0.0196(3) Uani 1 2 d S T P . .
O1 O 0.4726(5) 0.6773(4) 0.3576(3) 0.0221(9) 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 C2 1.907(6) . ?
Br2 C4 1.905(6) . ?
C1 C2 1.409(8) . ?
C1 C6 1.418(8) . ?
C1 O1 1.306(7) . ?
C2 C3 1.383(9) . ?
C3 H3 0.9500 . ?
C3 C4 1.394(9) . ?
C4 C5 1.364(9) . ?
C5 H5 0.9500 . ?
C5 C6 1.404(8) . ?
C6 C7 1.455(9) . ?
C7 H7 0.9500 . ?
C7 N1 1.274(8) . ?
C8 H8 1.0000 . ?
C8 C9 1.530(8) . ?
C8 C15 1.528(10) . ?
C8 N1 1.483(8) . ?
C9 C10 1.392(9) . ?
C9 C14 1.393(9) . ?
C10 H10 0.9500 . ?
C10 C11 1.393(10) . ?
C11 H11 0.9500 . ?
C11 C12 1.390(11) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(11) . ?
C13 H13 0.9500 . ?
C13 C14 1.390(9) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N1 Ni1 2.015(5) . ?
Ni1 O1 1.900(4) . ?
Ni1 O1 1.900(4) 2_656 ?

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
C2 C1 C6 115.5(5) . . ?
O1 C1 C2 120.3(5) . . ?
O1 C1 C6 124.2(5) . . ?
C1 C2 Br1 117.4(4) . . ?
C3 C2 Br1 118.5(5) . . ?
C3 C2 C1 123.9(6) . . ?
C2 C3 H3 121.1 . . ?
C2 C3 C4 117.8(6) . . ?
C4 C3 H3 121.1 . . ?
C3 C4 Br2 119.0(5) . . ?
C5 C4 Br2 119.5(5) . . ?
C5 C4 C3 121.5(5) . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.1(6) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C7 121.8(5) . . ?
C5 C6 C1 121.2(6) . . ?
C5 C6 C7 117.0(6) . . ?
C6 C7 H7 116.1 . . ?
N1 C7 C6 127.9(6) . . ?
N1 C7 H7 116.1 . . ?
C9 C8 H8 107.2 . . ?
C15 C8 H8 107.2 . . ?
C15 C8 C9 113.6(5) . . ?
N1 C8 H8 107.2 . . ?
N1 C8 C9 111.1(5) . . ?
N1 C8 C15 110.1(5) . . ?
C10 C9 C8 117.2(6) . . ?
C10 C9 C14 119.8(6) . . ?
C14 C9 C8 122.9(6) . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.9(6) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.1(7) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.0(7) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.4(7) . . ?
C14 C13 H13 119.8 . . ?
C9 C14 H14 120.1 . . ?
C13 C14 C9 119.9(6) . . ?
C13 C14 H14 120.1 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 N1 C8 115.4(5) . . ?
C7 N1 Ni1 121.5(4) . . ?
C8 N1 Ni1 123.1(4) . . ?
N1 Ni1 N1 115.3(3) . 2_656 ?
O1 Ni1 N1 92.62(19) . . ?
O1 Ni1 N1 107.12(19) . 2_656 ?
O1 Ni1 N1 92.62(19) 2_656 2_656 ?
O1 Ni1 N1 107.1(2) 2_656 . ?
O1 Ni1 O1 142.9(3) . 2_656 ?
C1 O1 Ni1 126.6(4) . . ?

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
Br1 C2 C3 C4 174.3(4) . . . . ?
Br2 C4 C5 C6 175.9(5) . . . . ?
C1 C2 C3 C4 -0.1(9) . . . . ?
C1 C6 C7 N1 -9.5(10) . . . . ?
C2 C1 C6 C5 1.7(8) . . . . ?
C2 C1 C6 C7 -175.3(5) . . . . ?
C2 C1 O1 Ni1 -163.4(4) . . . . ?
C2 C3 C4 Br2 -175.8(5) . . . . ?
C2 C3 C4 C5 1.7(10) . . . . ?
C3 C4 C5 C6 -1.5(10) . . . . ?
C4 C5 C6 C1 -0.2(9) . . . . ?
C4 C5 C6 C7 176.9(6) . . . . ?
C5 C6 C7 N1 173.4(6) . . . . ?
C6 C1 C2 Br1 -176.0(4) . . . . ?
C6 C1 C2 C3 -1.5(9) . . . . ?
C6 C1 O1 Ni1 15.4(8) . . . . ?
C6 C7 N1 C8 172.4(6) . . . . ?
C6 C7 N1 Ni1 -7.3(9) . . . . ?
C8 C9 C10 C11 -179.4(6) . . . . ?
C8 C9 C14 C13 178.0(6) . . . . ?
C9 C8 N1 C7 121.0(6) . . . . ?
C9 C8 N1 Ni1 -59.4(6) . . . . ?
C9 C10 C11 C12 1.9(10) . . . . ?
C10 C9 C14 C13 0.8(9) . . . . ?
C10 C11 C12 C13 -0.4(11) . . . . ?
C11 C12 C13 C14 -0.8(10) . . . . ?
C12 C13 C14 C9 0.6(9) . . . . ?
C14 C9 C10 C11 -2.1(9) . . . . ?
C15 C8 C9 C10 -177.9(5) . . . . ?
C15 C8 C9 C14 4.8(8) . . . . ?
C15 C8 N1 C7 -112.2(6) . . . . ?
C15 C8 N1 Ni1 67.5(6) . . . . ?
N1 C8 C9 C10 -53.1(7) . . . . ?
N1 C8 C9 C14 129.7(6) . . . . ?
N1 Ni1 O1 C1 93.3(5) 2_656 . . . ?
N1 Ni1 O1 C1 -24.2(5) . . . . ?
O1 C1 C2 Br1 2.9(7) . . . . ?
O1 C1 C2 C3 177.4(6) . . . . ?
O1 C1 C6 C5 -177.2(6) . . . . ?
O1 C1 C6 C7 5.8(9) . . . . ?
O1 Ni1 O1 C1 -147.5(5) 2_656 . . . ?


####################################################################### 
# 
# 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_hadi1411
_database_code_depnum_ccdc_archive 'CCDC 2000647'
loop_
_audit_author_name
_audit_author_address
'Olivier Blacque'
;University of Zurich
Switzerland
;
_audit_update_record             
;
2020-05-02 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
;

_audit_creation_date             2019-11-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H24 Br2 Cl2 N2 Ni O2'
_chemical_formula_sum            'C30 H24 Br2 Cl2 N2 Ni O2'
_chemical_formula_weight         733.94
_chemical_absolute_configuration ad
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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           5
_space_group_name_H-M_alt        'I 1 2 1'
_space_group_name_Hall           'I 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   10.1101(2)
_cell_length_b                   10.85749(19)
_cell_length_c                   13.0218(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.285(2)
_cell_angle_gamma                90
_cell_volume                     1364.86(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    13456
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      30.0140
_cell_measurement_theta_min      3.0230
_shelx_estimated_absorpt_T_max   0.747
_shelx_estimated_absorpt_T_min   0.433
_exptl_absorpt_coefficient_mu    3.867
_exptl_absorpt_correction_T_max  0.771
_exptl_absorpt_correction_T_min  0.530
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.786
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       trapezoid
_exptl_crystal_F_000             732
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -1 0.0398
-1 0 1 0.0398
0 1 1 0.0903
-4 -5 -1 0.0605
-1 1 0 0.0685
1 -1 0 0.0685

_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.08

_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14452
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         2.490
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  83.00   0.50    6.00    --    3.35  38.00   0.00  194
  2  ω    -22.00  78.00   0.50    6.00    --    3.35  77.00  90.00  200
  3  ω    -27.00  31.00   0.50    6.00    --   -4.60 -99.00 150.00  116
  4  ω    -27.00  26.00   0.50    6.00    --    3.35 -99.00 -30.00  106
  5  ω    -77.00   5.00   0.50    6.00    --    3.35 -19.00  30.00  164
  6  ω    -22.00  69.00   0.50    6.00    --   -4.60  57.00-180.00  182
  7  ω    -50.00 -23.00   0.50    6.00    --   -4.60 115.00   3.85   54
  8  ω    -52.00 -26.00   0.50    6.00    --   -4.60 119.00-116.49   52
  9  ω    -86.00  76.00   0.50    6.00    --   -4.60   0.00-180.00  324
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0147922000
_diffrn_orient_matrix_UB_12      -0.0446251000
_diffrn_orient_matrix_UB_13      -0.0416599000
_diffrn_orient_matrix_UB_21      -0.0612948000
_diffrn_orient_matrix_UB_22      0.0323594000
_diffrn_orient_matrix_UB_23      -0.0273487000
_diffrn_orient_matrix_UB_31      0.0377035000
_diffrn_orient_matrix_UB_32      0.0350625000
_diffrn_orient_matrix_UB_33      -0.0277747000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.894
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2758
_reflns_number_total             2797

_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015b)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1277 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.005(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2797
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0134
_refine_ls_R_factor_gt           0.0131
_refine_ls_restrained_S_all      1.045
_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)+(0.0200P)²+0.5222P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0334
_refine_ls_wR_factor_ref         0.0335
_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 Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.55429(2) 0.77384(2) 0.16882(2) 0.02192(7) Uani 1 1 d . . . . .
C1 C 0.3992(2) 0.6229(2) 0.26895(17) 0.0158(4) Uani 1 1 d . . . . .
C2 C 0.4157(2) 0.6548(2) 0.16785(19) 0.0178(5) Uani 1 1 d . . . . .
C3 C 0.3457(2) 0.5988(2) 0.07261(18) 0.0207(5) Uani 1 1 d . . . . .
H3 H 0.360437 0.623718 0.006933 0.025 Uiso 1 1 calc R . . . .
C4 C 0.2522(2) 0.5042(2) 0.07426(18) 0.0211(5) Uani 1 1 d . . . . .
C5 C 0.2293(2) 0.4700(2) 0.16926(18) 0.0192(5) Uani 1 1 d . . . . .
H5 H 0.164820 0.406310 0.169271 0.023 Uiso 1 1 calc R . . . .
C6 C 0.3002(2) 0.5282(2) 0.26608(18) 0.0171(4) Uani 1 1 d . . . . .
C7 C 0.2636(2) 0.4915(2) 0.36084(18) 0.0175(4) Uani 1 1 d . . . . .
H7 H 0.186924 0.437200 0.349447 0.021 Uiso 1 1 calc R . . . .
C8 C 0.2509(2) 0.4846(2) 0.53833(19) 0.0192(5) Uani 1 1 d . . . . .
H8 H 0.169446 0.433166 0.499116 0.023 Uiso 1 1 calc R . . . .
C9 C 0.3458(2) 0.4042(2) 0.62489(19) 0.0184(4) Uani 1 1 d . . . . .
C10 C 0.4077(3) 0.3027(2) 0.5928(2) 0.0265(6) Uani 1 1 d . . . . .
H10 H 0.391215 0.286784 0.518274 0.032 Uiso 1 1 calc R . . . .
C11 C 0.4927(3) 0.2247(3) 0.6677(2) 0.0330(6) Uani 1 1 d . . . . .
H11 H 0.535992 0.156834 0.644631 0.040 Uiso 1 1 calc R . . . .
C12 C 0.5147(3) 0.2456(2) 0.7765(2) 0.0325(6) Uani 1 1 d . . . . .
H12 H 0.573605 0.192450 0.828169 0.039 Uiso 1 1 calc R . . . .
C13 C 0.4507(3) 0.3436(3) 0.8095(2) 0.0282(6) Uani 1 1 d . . . . .
H13 H 0.463996 0.356646 0.884012 0.034 Uiso 1 1 calc R . . . .
C14 C 0.3671(2) 0.4234(2) 0.73451(18) 0.0217(5) Uani 1 1 d . . . . .
H14 H 0.324320 0.491302 0.757976 0.026 Uiso 1 1 calc R . . . .
C15 C 0.1955(2) 0.5984(2) 0.57971(19) 0.0243(5) Uani 1 1 d . . . . .
H15A H 0.272985 0.651433 0.617735 0.036 Uiso 1 1 calc GR . . . .
H15B H 0.143706 0.573503 0.629098 0.036 Uiso 1 1 calc GR . . . .
H15C H 0.134006 0.643613 0.518997 0.036 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.16953(7) 0.42607(6) -0.04432(5) 0.03096(14) Uani 1 1 d . . . . .
N1 N 0.32274(19) 0.52376(17) 0.45868(15) 0.0165(4) Uani 1 1 d . . . . .
Ni1 Ni 0.500000 0.62030(3) 0.500000 0.01563(9) Uani 1 2 d S T P . .
O1 O 0.47114(16) 0.67772(15) 0.35619(13) 0.0182(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
Br1 C2 1.903(2) . ?
C1 C2 1.419(3) . ?
C1 C6 1.427(3) . ?
C1 O1 1.298(3) . ?
C2 C3 1.374(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.401(3) . ?
C4 C5 1.376(3) . ?
C4 Cl1 1.742(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.402(3) . ?
C6 C7 1.445(3) . ?
C7 H7 0.9500 . ?
C7 N1 1.285(3) . ?
C8 H8 1.0000 . ?
C8 C9 1.520(3) . ?
C8 C15 1.520(3) . ?
C8 N1 1.494(3) . ?
C9 C10 1.392(3) . ?
C9 C14 1.394(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.382(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.379(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.389(4) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N1 Ni1 2.0066(19) . ?
Ni1 O1 1.9120(16) 2_656 ?
Ni1 O1 1.9120(16) . ?

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
C2 C1 C6 115.3(2) . . ?
O1 C1 C2 120.7(2) . . ?
O1 C1 C6 124.0(2) . . ?
C1 C2 Br1 116.71(17) . . ?
C3 C2 Br1 119.18(17) . . ?
C3 C2 C1 123.9(2) . . ?
C2 C3 H3 120.7 . . ?
C2 C3 C4 118.7(2) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 Cl1 119.45(18) . . ?
C5 C4 C3 120.4(2) . . ?
C5 C4 Cl1 120.07(19) . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.6(2) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C7 122.1(2) . . ?
C5 C6 C1 121.0(2) . . ?
C5 C6 C7 116.8(2) . . ?
C6 C7 H7 116.2 . . ?
N1 C7 C6 127.6(2) . . ?
N1 C7 H7 116.2 . . ?
C9 C8 H8 107.5 . . ?
C9 C8 C15 114.93(19) . . ?
C15 C8 H8 107.5 . . ?
N1 C8 H8 107.5 . . ?
N1 C8 C9 110.37(18) . . ?
N1 C8 C15 108.73(19) . . ?
C10 C9 C8 118.2(2) . . ?
C10 C9 C14 118.6(2) . . ?
C14 C9 C8 123.0(2) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 120.9(2) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.9(2) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.8(2) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C9 C14 H14 119.9 . . ?
C13 C14 C9 120.2(2) . . ?
C13 C14 H14 119.9 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 N1 C8 115.58(19) . . ?
C7 N1 Ni1 121.58(15) . . ?
C8 N1 Ni1 122.85(14) . . ?
N1 Ni1 N1 117.02(11) 2_656 . ?
O1 Ni1 N1 107.29(7) . 2_656 ?
O1 Ni1 N1 92.49(7) . . ?
O1 Ni1 N1 107.29(7) 2_656 . ?
O1 Ni1 N1 92.49(7) 2_656 2_656 ?
O1 Ni1 O1 141.94(10) 2_656 . ?
C1 O1 Ni1 126.20(14) . . ?

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
Br1 C2 C3 C4 174.79(17) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C1 C6 C7 N1 -9.5(4) . . . . ?
C2 C1 C6 C5 2.0(3) . . . . ?
C2 C1 C6 C7 -175.2(2) . . . . ?
C2 C1 O1 Ni1 -162.41(16) . . . . ?
C2 C3 C4 C5 1.2(3) . . . . ?
C2 C3 C4 Cl1 -176.46(18) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C4 C5 C6 C1 -0.9(3) . . . . ?
C4 C5 C6 C7 176.4(2) . . . . ?
C5 C6 C7 N1 173.2(2) . . . . ?
C6 C1 C2 Br1 -176.46(16) . . . . ?
C6 C1 C2 C3 -1.5(3) . . . . ?
C6 C1 O1 Ni1 17.4(3) . . . . ?
C6 C7 N1 C8 172.2(2) . . . . ?
C6 C7 N1 Ni1 -7.8(3) . . . . ?
C8 C9 C10 C11 -178.6(2) . . . . ?
C8 C9 C14 C13 177.3(2) . . . . ?
C9 C8 N1 C7 120.9(2) . . . . ?
C9 C8 N1 Ni1 -59.1(2) . . . . ?
C9 C10 C11 C12 1.5(4) . . . . ?
C10 C9 C14 C13 1.2(3) . . . . ?
C10 C11 C12 C13 0.5(4) . . . . ?
C11 C12 C13 C14 -1.6(4) . . . . ?
C12 C13 C14 C9 0.7(4) . . . . ?
C14 C9 C10 C11 -2.3(4) . . . . ?
C15 C8 C9 C10 -175.9(2) . . . . ?
C15 C8 C9 C14 7.9(3) . . . . ?
C15 C8 N1 C7 -112.2(2) . . . . ?
C15 C8 N1 Ni1 67.8(2) . . . . ?
Cl1 C4 C5 C6 176.95(17) . . . . ?
N1 C8 C9 C10 -52.5(3) . . . . ?
N1 C8 C9 C14 131.3(2) . . . . ?
O1 C1 C2 Br1 3.4(3) . . . . ?
O1 C1 C2 C3 178.4(2) . . . . ?
O1 C1 C6 C5 -177.9(2) . . . . ?
O1 C1 C6 C7 4.9(3) . . . . ?


####################################################################### 
# 
# 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_hadi0701
_database_code_depnum_ccdc_archive 'CCDC 2000645'
loop_
_audit_author_name
_audit_author_address
'Olivier Blacque'
;University of Zurich
Switzerland
;
_audit_update_record             
;
2020-05-02 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
;

_audit_creation_date             2020-01-28
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H24 Cl4 N2 Ni O2'
_chemical_formula_sum            'C30 H24 Cl4 N2 Ni O2'
_chemical_formula_weight         645.02
_chemical_absolute_configuration ad
_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'
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'
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           5
_space_group_name_H-M_alt        'I 1 2 1'
_space_group_name_Hall           'I 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   9.98147(15)
_cell_length_b                   10.86524(17)
_cell_length_c                   12.8851(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.6972(17)
_cell_angle_gamma                90
_cell_volume                     1338.49(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8972
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      77.7550
_cell_measurement_theta_min      4.9640
_shelx_estimated_absorpt_T_max   0.929
_shelx_estimated_absorpt_T_min   0.662
_exptl_absorpt_coefficient_mu    4.989
_exptl_absorpt_correction_T_max  0.934
_exptl_absorpt_correction_T_min  0.723
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             660
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -1 0 0.0108
3 5 0 0.0362
-2 -4 -5 0.0443
0 2 5 0.0417
0 -2 -5 0.0417
3 3 -5 0.0169
-3 -3 5 0.0349
-1 1 0 0.0028

_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.015

_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13792
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.489
_diffrn_reflns_theta_min         4.971
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -82.00   2.00   0.50    2.50    --  -51.46 107.00 137.00  168
  2  ω    -35.00  -6.00   0.50   10.00    --  -84.25  30.00  60.00   58
  3  ω    -35.00  -6.00   0.50   10.00    --  -84.25  30.00  90.00   58
  4  ω    -65.00  21.00   0.50    2.50    --  -51.46  57.00  90.00  172
  5  ω    -82.00  -8.00   0.50   10.00    --  -84.25 107.00 137.00  148
  6  ω   -124.00 -38.00   0.50    2.50    --  -51.46 -57.00 -30.00  172
  7  ω    -35.00  -6.00   0.50   10.00    --  -84.25  30.00-120.00   58
  8  ω    -35.00  -6.00   0.50   10.00    --  -84.25  30.00-150.00   58
  9  ω   -125.00 -73.00   0.50    2.50    --  -51.46-125.00-180.00  104
 10  ω   -125.00 -73.00   0.50    2.50    --  -51.46-125.00 -60.00  104
 11  ω   -125.00 -73.00   0.50    2.50    --  -51.46-125.00  60.00  104
 12  ω   -124.00 -38.00   0.50    2.50    --  -51.46 -57.00 120.00  172
 13  ω     20.00  88.00   0.50    2.50    --   51.46-107.00  38.00  136
 14  ω     33.00 105.00   0.50   10.00    --  105.75 -77.00  60.00  144
 15  ω     62.00 102.00   0.50   10.00    --  105.75-111.00   0.00   80
 16  ω     72.00 106.00   0.50   10.00    --  105.75 -94.00  30.00   68
 17  ω     77.00 104.00   0.50   10.00    --  105.75 -77.00 150.00   54
 18  ω     96.00 178.00   0.50   10.00    --  105.75  15.00  60.00  164
 19  ω    145.00 176.00   0.50   10.00    --  105.75  45.00 -30.00   62
 20  ω    109.00 139.00   0.50   10.00    --  105.75  45.00 -30.00   60
 21  ω    102.00 178.00   0.50   10.00    --  105.75 111.00  60.00  152
 22  ω    104.00 178.00   0.50   10.00    --  105.75 107.00 137.00  148
 23  ω     95.00 178.00   0.50   10.00    --  105.75  45.00  60.00  166
 24  ω     96.00 178.00   0.50   10.00    --  105.75  15.00-120.00  164
 25  ω     97.00 178.00   0.50   10.00    --  105.75  30.00-180.00  162
 26  ω     84.00 178.00   0.50   10.00    --  105.75  77.00-180.00  188
 27  ω     91.00 177.00   0.50   10.00    --  105.75  61.00  30.00  172
 28  ω     62.00 146.00   0.50   10.00    --  105.75 178.00-180.00  168
 29  ω     35.00  71.00   0.50   10.00    --  105.75 -61.00 150.00   72
 30  ω     30.00 109.00   0.50   10.00    --  105.75-111.00  90.00  158
 31  ω     43.00  68.00   0.50   10.00    --  105.75 -61.00  60.00   50
 32  ω     29.00 108.00   0.50   10.00    --  105.75-107.00  38.00  158
 33  ω     30.00 109.00   0.50   10.00    --  105.75-111.00 -30.00  158
 34  ω     42.00 124.00   0.50   10.00    --  105.75-140.00-137.79  164
 35  ω     44.00  94.00   0.50   10.00    --  105.75-111.00-120.00  100
 36  ω     33.00 105.00   0.50   10.00    --  105.75 -77.00-180.00  144
 37  ω     30.00 109.00   0.50   10.00    --  105.75-111.00 -90.00  158
 38  ω     33.00 105.00   0.50   10.00    --  105.75 -77.00-150.00  144
 39  ω     33.00 105.00   0.50   10.00    --  105.75 -77.00-120.00  144
 40  ω     30.00 109.00   0.50   10.00    --  105.75-111.00-150.00  158
 41  ω     33.00 105.00   0.50   10.00    --  105.75 -77.00 -90.00  144
 42  ω     30.00 109.00   0.50   10.00    --  105.75-111.00 -60.00  158
 43  ω     30.00 106.00   0.50   10.00    --  105.75 -94.00  90.00  152
 44  ω     30.00 109.00   0.50   10.00    --  105.75-111.00 150.00  158
 45  ω     34.00  68.00   0.50   10.00    --  105.75 -94.00  30.00   68
 46  ω   -161.00 -82.00   0.50   10.00    --  -84.25-107.00  38.00  158
 47  ω   -162.00 -75.00   0.50   10.00    --  -84.25 -30.00 -90.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0020358000
_diffrn_orient_matrix_UB_12      -0.1417312000
_diffrn_orient_matrix_UB_13      -0.0046449000
_diffrn_orient_matrix_UB_21      -0.0074977000
_diffrn_orient_matrix_UB_22      0.0050618000
_diffrn_orient_matrix_UB_23      -0.1210296000
_diffrn_orient_matrix_UB_31      0.1608947000
_diffrn_orient_matrix_UB_32      -0.0016521000
_diffrn_orient_matrix_UB_33      0.0302290000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.892
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                2675
_reflns_number_total             2723

_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 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015a)'
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 1232 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.006(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2723
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0225
_refine_ls_R_factor_gt           0.0219
_refine_ls_restrained_S_all      1.058
_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)+(0.0371P)²+0.4488P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0571
_refine_ls_wR_factor_ref         0.0573
_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 Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.500000 0.62582(5) 0.500000 0.02467(15) Uani 1 2 d S T P . .
Cl1 Cl 0.45959(6) 0.77175(6) 0.83583(5) 0.03225(14) Uani 1 1 d . . . . .
Cl2 Cl 0.83105(7) 0.42913(7) 1.04664(5) 0.03963(17) Uani 1 1 d . . . . .
O1 O 0.52874(18) 0.68259(16) 0.64509(13) 0.0269(3) Uani 1 1 d . . . . .
N1 N 0.6779(2) 0.52767(18) 0.54016(16) 0.0248(4) Uani 1 1 d . . . . .
C1 C 0.6008(2) 0.6269(3) 0.73237(18) 0.0247(4) Uani 1 1 d . . . . .
C2 C 0.5841(2) 0.6596(2) 0.83473(19) 0.0262(5) Uani 1 1 d . . . . .
C3 C 0.6547(3) 0.6029(3) 0.9304(2) 0.0299(5) Uani 1 1 d . . . . .
H3 H 0.640403 0.627971 0.997075 0.036 Uiso 1 1 calc R U . . .
C4 C 0.7479(3) 0.5077(2) 0.9276(2) 0.0295(5) Uani 1 1 d . . . . .
C5 C 0.7711(2) 0.4730(3) 0.8316(2) 0.0282(5) Uani 1 1 d . . . . .
H5 H 0.835696 0.408973 0.830941 0.034 Uiso 1 1 calc R U . . .
C6 C 0.6994(2) 0.5318(2) 0.73454(19) 0.0252(5) Uani 1 1 d . . . . .
C7 C 0.7369(2) 0.4950(2) 0.6385(2) 0.0264(5) Uani 1 1 d . . . . .
H7 H 0.813972 0.440296 0.649513 0.032 Uiso 1 1 calc R U . . .
C8 C 0.7504(2) 0.4881(2) 0.4592(2) 0.0279(5) Uani 1 1 d . . . . .
H8 H 0.832938 0.437233 0.498326 0.034 Uiso 1 1 calc R U . . .
C9 C 0.6556(2) 0.4076(2) 0.3729(2) 0.0264(5) Uani 1 1 d . . . . .
C10 C 0.5923(3) 0.3064(3) 0.4064(2) 0.0340(6) Uani 1 1 d . . . . .
H10 H 0.609081 0.290702 0.481592 0.041 Uiso 1 1 calc R U . . .
C11 C 0.5057(3) 0.2287(3) 0.3316(3) 0.0404(6) Uani 1 1 d . . . . .
H11 H 0.462019 0.161029 0.355437 0.048 Uiso 1 1 calc R U . . .
C12 C 0.4827(3) 0.2497(3) 0.2218(2) 0.0400(6) Uani 1 1 d . . . . .
H12 H 0.422020 0.197324 0.170105 0.048 Uiso 1 1 calc R U . . .
C13 C 0.5481(3) 0.3467(3) 0.1880(2) 0.0364(6) Uani 1 1 d . . . . .
H13 H 0.534672 0.359442 0.112725 0.044 Uiso 1 1 calc R U . . .
C14 C 0.6334(3) 0.4260(2) 0.2625(2) 0.0296(5) Uani 1 1 d . . . . .
H14 H 0.676864 0.493368 0.237958 0.036 Uiso 1 1 calc R U . . .
C15 C 0.8057(3) 0.6018(3) 0.4159(2) 0.0340(6) Uani 1 1 d . . . . .
H15A H 0.726976 0.653315 0.376232 0.051 Uiso 1 1 calc R U . . .
H15B H 0.859910 0.576557 0.366996 0.051 Uiso 1 1 calc R U . . .
H15C H 0.865761 0.648786 0.476452 0.051 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
Ni1 O1 1.9103(17) 2_656 ?
Ni1 O1 1.9104(17) . ?
Ni1 N1 2.008(2) 2_656 ?
Ni1 N1 2.0079(19) . ?
Cl1 C2 1.743(2) . ?
Cl2 C4 1.743(3) . ?
O1 C1 1.298(3) . ?
N1 C7 1.284(3) . ?
N1 C8 1.493(3) . ?
C1 C2 1.421(3) . ?
C1 C6 1.421(3) . ?
C2 C3 1.377(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.399(4) . ?
C4 C5 1.374(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.404(3) . ?
C6 C7 1.448(3) . ?
C7 H7 0.9500 . ?
C8 H8 1.0000 . ?
C8 C9 1.514(3) . ?
C8 C15 1.523(4) . ?
C9 C10 1.397(4) . ?
C9 C14 1.390(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.382(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.375(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.385(4) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
O1 Ni1 O1 142.33(11) 2_656 . ?
O1 Ni1 N1 107.26(8) 2_656 . ?
O1 Ni1 N1 92.65(8) . . ?
O1 Ni1 N1 92.65(8) 2_656 2_656 ?
O1 Ni1 N1 107.26(8) . 2_656 ?
N1 Ni1 N1 115.84(12) 2_656 . ?
C1 O1 Ni1 125.98(16) . . ?
C7 N1 Ni1 121.45(16) . . ?
C7 N1 C8 115.67(19) . . ?
C8 N1 Ni1 122.88(15) . . ?
O1 C1 C2 120.3(2) . . ?
O1 C1 C6 124.3(2) . . ?
C6 C1 C2 115.4(2) . . ?
C1 C2 Cl1 117.15(18) . . ?
C3 C2 Cl1 119.21(18) . . ?
C3 C2 C1 123.5(2) . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.7(2) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 Cl2 119.39(19) . . ?
C5 C4 Cl2 119.8(2) . . ?
C5 C4 C3 120.8(2) . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.1(2) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C7 122.1(2) . . ?
C5 C6 C1 121.4(2) . . ?
C5 C6 C7 116.4(2) . . ?
N1 C7 C6 127.5(2) . . ?
N1 C7 H7 116.2 . . ?
C6 C7 H7 116.2 . . ?
N1 C8 H8 107.5 . . ?
N1 C8 C9 110.69(19) . . ?
N1 C8 C15 108.8(2) . . ?
C9 C8 H8 107.5 . . ?
C9 C8 C15 114.5(2) . . ?
C15 C8 H8 107.5 . . ?
C10 C9 C8 118.1(2) . . ?
C14 C9 C8 123.4(2) . . ?
C14 C9 C10 118.4(2) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 119.9(3) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.7(3) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.7(3) . . ?
C14 C13 H13 119.7 . . ?
C9 C14 H14 119.8 . . ?
C13 C14 C9 120.3(2) . . ?
C13 C14 H14 119.8 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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 O1 C1 C2 -162.91(17) . . . . ?
Ni1 O1 C1 C6 17.1(3) . . . . ?
Ni1 N1 C7 C6 -7.6(3) . . . . ?
Ni1 N1 C8 C9 -59.9(2) . . . . ?
Ni1 N1 C8 C15 66.8(2) . . . . ?
Cl1 C2 C3 C4 176.04(19) . . . . ?
Cl2 C4 C5 C6 176.92(18) . . . . ?
O1 C1 C2 Cl1 2.4(3) . . . . ?
O1 C1 C2 C3 178.6(2) . . . . ?
O1 C1 C6 C5 -178.2(2) . . . . ?
O1 C1 C6 C7 5.1(4) . . . . ?
N1 C8 C9 C10 -52.0(3) . . . . ?
N1 C8 C9 C14 131.0(2) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C1 C6 C7 N1 -9.7(4) . . . . ?
C2 C1 C6 C5 1.9(3) . . . . ?
C2 C1 C6 C7 -174.8(2) . . . . ?
C2 C3 C4 Cl2 -176.48(19) . . . . ?
C2 C3 C4 C5 1.4(4) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
C4 C5 C6 C1 -0.8(4) . . . . ?
C4 C5 C6 C7 176.1(2) . . . . ?
C5 C6 C7 N1 173.5(2) . . . . ?
C6 C1 C2 Cl1 -177.68(18) . . . . ?
C6 C1 C2 C3 -1.4(3) . . . . ?
C7 N1 C8 C9 120.2(2) . . . . ?
C7 N1 C8 C15 -113.1(2) . . . . ?
C8 N1 C7 C6 172.4(2) . . . . ?
C8 C9 C10 C11 -179.4(2) . . . . ?
C8 C9 C14 C13 178.3(2) . . . . ?
C9 C10 C11 C12 1.1(4) . . . . ?
C10 C9 C14 C13 1.2(4) . . . . ?
C10 C11 C12 C13 1.0(4) . . . . ?
C11 C12 C13 C14 -2.0(4) . . . . ?
C12 C13 C14 C9 0.9(4) . . . . ?
C14 C9 C10 C11 -2.2(4) . . . . ?
C15 C8 C9 C10 -175.4(2) . . . . ?
C15 C8 C9 C14 7.5(3) . . . . ?


####################################################################### 
# 
# 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_hadi3101
_database_code_depnum_ccdc_archive 'CCDC 2149672'
loop_
_audit_author_name
_audit_author_address
' Olivier Blacque'
;University of Zurich
Switzerland
;
_audit_update_record             
;
2022-02-02 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
;

_audit_creation_date             2022-01-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H24 Br2 Cl2 N2 Ni O2'
_chemical_formula_sum            'C30 H24 Br2 Cl2 N2 Ni O2'
_chemical_formula_weight         733.94
_chemical_absolute_configuration .
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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           5
_space_group_name_H-M_alt        'I 1 2 1'
_space_group_name_Hall           'I 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   10.0967(1)
_cell_length_b                   10.8500(1)
_cell_length_c                   13.0172(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.314(1)
_cell_angle_gamma                90
_cell_volume                     1361.41(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    14982
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      32.6350
_cell_measurement_theta_min      2.4790
_shelx_estimated_absorpt_T_max   0.594
_shelx_estimated_absorpt_T_min   0.469
_exptl_absorpt_coefficient_mu    3.877
_exptl_absorpt_correction_T_max  0.645
_exptl_absorpt_correction_T_min  0.544
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.790
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             732
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 1 0.0755
0 1 -1 0.0755
0 1 1 0.0797
0 -1 -1 0.0797
-1 0 1 0.0741
1 0 -1 0.0741
1 -1 1 0.0936
-1 1 -1 0.0936
5 3 -2 0.0893
-5 -3 2 0.0893
2 -5 2 0.0656
-2 5 -2 0.0796

_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15

_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17509
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         2.256
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -70.00 109.00   1.00    6.50    --   19.62   0.00  60.00  179
  2  ω   -110.00 -61.00   1.00    6.50    --  -20.24-178.00  90.00   49
  3  ω   -110.00 -61.00   1.00    6.50    --  -20.24-178.00   0.00   49
  4  ω    -47.00  56.00   1.00    6.50    --  -20.24  37.00 -60.00  103
  5  ω    -42.00  13.00   1.00    6.50    --  -20.24 -77.00 120.00   55
  6  ω    -42.00  13.00   1.00    6.50    --  -20.24 -77.00   0.00   55
  7  ω    -42.00  13.00   1.00    6.50    --  -20.24 -77.00-180.00   55
  8  ω    -42.00  13.00   1.00    6.50    --  -20.24 -77.00 -90.00   55
  9  ω    -42.00  13.00   1.00    6.50    --  -20.24 -77.00  60.00   55
 10  ω   -109.00 -58.00   1.00    6.50    --  -20.24 178.00-120.00   51
 11  ω    -47.00  56.00   1.00    6.50    --  -20.24  37.00  30.00  103
 12  ω    -15.00  19.00   1.00    6.50    --   19.62 -99.00  30.00   34
 13  ω    -15.00  62.00   1.00    6.50    --   19.62 -99.00-180.00   77
 14  ω    -94.00   9.00   1.00    6.50    --  -20.24 -57.00  60.00  103
 15  ω   -109.00 -58.00   1.00    6.50    --  -20.24 178.00-180.00   51
 16  ω    -54.00  21.00   1.00    6.50    --  -20.24  77.00  60.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0625618000
_diffrn_orient_matrix_UB_12      -0.0147474000
_diffrn_orient_matrix_UB_13      0.0114709000
_diffrn_orient_matrix_UB_21      -0.0139887000
_diffrn_orient_matrix_UB_22      -0.0465091000
_diffrn_orient_matrix_UB_23      -0.0401061000
_diffrn_orient_matrix_UB_31      0.0361162000
_diffrn_orient_matrix_UB_32      -0.0435381000
_diffrn_orient_matrix_UB_33      0.0389367000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.895
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2755
_reflns_number_total             2792
_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 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (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 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 1270 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.006(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2792
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0141
_refine_ls_R_factor_gt           0.0136
_refine_ls_restrained_S_all      1.064
_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)+(0.0142P)²+0.6728P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0325
_refine_ls_wR_factor_ref         0.0327
_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 Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.55421(2) 0.22617(2) 0.16864(2) 0.02211(7) Uani 1 1 d . . . . .
C1 C 0.3991(2) 0.3772(2) 0.26870(18) 0.0157(4) Uani 1 1 d . . . . .
C2 C 0.4155(3) 0.3454(2) 0.1678(2) 0.0180(5) Uani 1 1 d . . . . .
C3 C 0.3456(3) 0.4014(2) 0.07264(19) 0.0208(5) Uani 1 1 d . . . . .
H3 H 0.360015 0.376396 0.006849 0.025 Uiso 1 1 calc R U . . .
C4 C 0.2525(3) 0.4962(2) 0.0748(2) 0.0208(5) Uani 1 1 d . . . . .
C5 C 0.2294(3) 0.5306(2) 0.16932(19) 0.0195(5) Uani 1 1 d . . . . .
H5 H 0.164805 0.594266 0.169298 0.023 Uiso 1 1 calc R U . . .
C6 C 0.3007(2) 0.4721(2) 0.2662(2) 0.0170(5) Uani 1 1 d . . . . .
C7 C 0.2640(3) 0.5086(2) 0.3609(2) 0.0175(5) Uani 1 1 d . . . . .
H7 H 0.187404 0.563144 0.349526 0.021 Uiso 1 1 calc R U . . .
C8 C 0.2510(3) 0.5150(2) 0.5381(2) 0.0188(5) Uani 1 1 d . . . . .
H8 H 0.169509 0.566429 0.498712 0.023 Uiso 1 1 calc R U . . .
C9 C 0.3460(3) 0.5957(2) 0.6246(2) 0.0176(5) Uani 1 1 d . . . . .
C10 C 0.3675(3) 0.5764(2) 0.7344(2) 0.0216(5) Uani 1 1 d . . . . .
H10 H 0.325033 0.508194 0.757818 0.026 Uiso 1 1 calc R U . . .
C11 C 0.4505(3) 0.6565(3) 0.8092(2) 0.0277(6) Uani 1 1 d . . . . .
H11 H 0.463653 0.643581 0.883743 0.033 Uiso 1 1 calc R U . . .
C12 C 0.5143(3) 0.7548(2) 0.7761(2) 0.0328(7) Uani 1 1 d . . . . .
H12 H 0.572875 0.808286 0.827819 0.039 Uiso 1 1 calc R U . . .
C13 C 0.4925(3) 0.7754(3) 0.6674(3) 0.0332(7) Uani 1 1 d . . . . .
H13 H 0.536020 0.843220 0.644339 0.040 Uiso 1 1 calc R U . . .
C14 C 0.4076(3) 0.6972(2) 0.5924(2) 0.0262(6) Uani 1 1 d . . . . .
H14 H 0.391036 0.713124 0.517886 0.031 Uiso 1 1 calc R U . . .
C15 C 0.1954(3) 0.4015(3) 0.5795(2) 0.0238(6) Uani 1 1 d . . . . .
H15A H 0.134847 0.355624 0.518689 0.036 Uiso 1 1 calc R U . . .
H15B H 0.142540 0.426654 0.628060 0.036 Uiso 1 1 calc R U . . .
H15C H 0.273051 0.348920 0.618485 0.036 Uiso 1 1 calc R U . . .
Cl1 Cl 0.16941(7) 0.57434(7) -0.04408(5) 0.03127(16) Uani 1 1 d . . . . .
N1 N 0.3229(2) 0.47600(18) 0.45879(16) 0.0166(4) Uani 1 1 d . . . . .
Ni1 Ni 0.500000 0.37886(4) 0.500000 0.01523(10) Uani 1 2 d S T P . .
O1 O 0.47155(17) 0.32228(16) 0.35611(13) 0.0181(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
Br1 C2 1.904(2) . ?
C1 C2 1.414(3) . ?
C1 C6 1.424(3) . ?
C1 O1 1.300(3) . ?
C2 C3 1.372(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.399(4) . ?
C4 C5 1.370(4) . ?
C4 Cl1 1.745(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.404(3) . ?
C6 C7 1.445(3) . ?
C7 H7 0.9500 . ?
C7 N1 1.285(3) . ?
C8 H8 1.0000 . ?
C8 C9 1.521(3) . ?
C8 C15 1.517(4) . ?
C8 N1 1.489(3) . ?
C9 C10 1.395(3) . ?
C9 C14 1.389(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.379(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(4) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N1 Ni1 2.006(2) . ?
Ni1 O1 1.9098(17) . ?
Ni1 O1 1.9098(17) 2_656 ?

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
C2 C1 C6 115.4(2) . . ?
O1 C1 C2 120.7(2) . . ?
O1 C1 C6 123.9(2) . . ?
C1 C2 Br1 116.74(18) . . ?
C3 C2 Br1 119.04(19) . . ?
C3 C2 C1 124.0(2) . . ?
C2 C3 H3 120.8 . . ?
C2 C3 C4 118.4(2) . . ?
C4 C3 H3 120.8 . . ?
C3 C4 Cl1 119.2(2) . . ?
C5 C4 C3 120.9(2) . . ?
C5 C4 Cl1 119.9(2) . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.3(2) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C7 122.2(2) . . ?
C5 C6 C1 121.0(2) . . ?
C5 C6 C7 116.7(2) . . ?
C6 C7 H7 116.2 . . ?
N1 C7 C6 127.6(2) . . ?
N1 C7 H7 116.2 . . ?
C9 C8 H8 107.5 . . ?
C15 C8 H8 107.5 . . ?
C15 C8 C9 115.0(2) . . ?
N1 C8 H8 107.5 . . ?
N1 C8 C9 110.3(2) . . ?
N1 C8 C15 108.9(2) . . ?
C10 C9 C8 122.9(2) . . ?
C14 C9 C8 118.2(2) . . ?
C14 C9 C10 118.8(2) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.8(3) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 119.9(3) . . ?
C14 C13 H13 120.0 . . ?
C9 C14 H14 119.6 . . ?
C13 C14 C9 120.9(3) . . ?
C13 C14 H14 119.6 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 N1 C8 115.6(2) . . ?
C7 N1 Ni1 121.50(17) . . ?
C8 N1 Ni1 122.93(15) . . ?
N1 Ni1 N1 116.61(12) 2_656 . ?
O1 Ni1 N1 107.04(8) . 2_656 ?
O1 Ni1 N1 92.56(7) . . ?
O1 Ni1 N1 107.04(8) 2_656 . ?
O1 Ni1 N1 92.56(7) 2_656 2_656 ?
O1 Ni1 O1 142.50(11) . 2_656 ?
C1 O1 Ni1 126.32(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
Br1 C2 C3 C4 -174.62(18) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C1 C6 C7 N1 9.6(4) . . . . ?
C2 C1 C6 C5 -1.7(3) . . . . ?
C2 C1 C6 C7 175.1(2) . . . . ?
C2 C1 O1 Ni1 162.80(17) . . . . ?
C2 C3 C4 C5 -1.4(4) . . . . ?
C2 C3 C4 Cl1 176.6(2) . . . . ?
C3 C4 C5 C6 0.9(4) . . . . ?
C4 C5 C6 C1 0.7(4) . . . . ?
C4 C5 C6 C7 -176.3(2) . . . . ?
C5 C6 C7 N1 -173.5(2) . . . . ?
C6 C1 C2 Br1 176.23(17) . . . . ?
C6 C1 C2 C3 1.3(4) . . . . ?
C6 C1 O1 Ni1 -16.7(3) . . . . ?
C6 C7 N1 C8 -172.2(2) . . . . ?
C6 C7 N1 Ni1 7.8(3) . . . . ?
C8 C9 C10 C11 -177.1(2) . . . . ?
C8 C9 C14 C13 178.6(2) . . . . ?
C9 C8 N1 C7 -120.5(2) . . . . ?
C9 C8 N1 Ni1 59.5(2) . . . . ?
C9 C10 C11 C12 -0.9(4) . . . . ?
C10 C9 C14 C13 2.3(4) . . . . ?
C10 C11 C12 C13 1.5(4) . . . . ?
C11 C12 C13 C14 -0.2(4) . . . . ?
C12 C13 C14 C9 -1.7(4) . . . . ?
C14 C9 C10 C11 -1.0(4) . . . . ?
C15 C8 C9 C10 -7.7(3) . . . . ?
C15 C8 C9 C14 176.2(2) . . . . ?
C15 C8 N1 C7 112.4(2) . . . . ?
C15 C8 N1 Ni1 -67.6(2) . . . . ?
Cl1 C4 C5 C6 -176.99(19) . . . . ?
N1 C8 C9 C10 -131.3(2) . . . . ?
N1 C8 C9 C14 52.6(3) . . . . ?
O1 C1 C2 Br1 -3.3(3) . . . . ?
O1 C1 C2 C3 -178.2(2) . . . . ?
O1 C1 C6 C5 177.8(2) . . . . ?
O1 C1 C6 C7 -5.4(4) . . . . ?


####################################################################### 
# 
# 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_hadi1211
_database_code_depnum_ccdc_archive 'CCDC 2000649'
loop_
_audit_author_name
_audit_author_address
'Olivier Blacque'
;University of Zurich
Switzerland
;
_audit_update_record             
;
2020-05-02 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
;

_audit_creation_date             2019-11-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H24 Br4 N2 Ni O2'
_chemical_formula_sum            'C30 H24 Br4 N2 Ni O2'
_chemical_formula_weight         822.86
_chemical_absolute_configuration ad
_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'
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'
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           5
_space_group_name_H-M_alt        'I 1 2 1'
_space_group_name_Hall           'I 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   10.10590(10)
_cell_length_b                   10.93120(10)
_cell_length_c                   13.06820(10)
_cell_angle_alpha                90
_cell_angle_beta                 106.6210(10)
_cell_angle_gamma                90
_cell_volume                     1383.32(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    14049
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      78.1370
_cell_measurement_theta_min      4.8980
_shelx_estimated_absorpt_T_max   0.856
_shelx_estimated_absorpt_T_min   0.500
_exptl_absorpt_coefficient_mu    8.042
_exptl_absorpt_correction_T_max  0.878
_exptl_absorpt_correction_T_min  0.556
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.976
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             804
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -1 0.0157
-1 0 1 0.0010
3 3 5 0.0281
-2 -5 2 0.0332
-3 -5 -2 0.0469
1 4 -5 0.0390
3 -6 3 0.0514
1 -5 -1 0.0382

_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02

_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14700
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.424
_diffrn_reflns_theta_min         4.909
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  26.00   0.50    0.70    --   51.72 -19.00  30.00  106
  2  ω     38.00 124.00   0.50    0.70    --   51.72  57.00  90.00  172
  3  ω     97.00 178.00   0.50    2.80    --  105.75  30.00  30.00  162
  4  ω     95.00 178.00   0.50    2.80    --  105.75  48.00 -40.42  166
  5  ω     97.00 178.00   0.50    2.80    --  105.75  30.00 -90.00  162
  6  ω     96.00 178.00   0.50    2.80    --  105.75  15.00-150.00  164
  7  ω     96.00 178.00   0.50    2.80    --  105.75  15.00 -60.00  164
  8  ω     97.00 178.00   0.50    2.80    --  105.75  30.00  60.00  162
  9  ω     94.00 178.00   0.50    2.80    --  105.75  45.00 -90.00  168
 10  ω     92.00 178.00   0.50    2.80    --  105.75  57.00-132.70  172
 11  ω     91.00 177.00   0.50    2.80    --  105.75  60.00 -67.85  172
 12  ω     94.00 178.00   0.50    2.80    --  105.75  45.00-150.00  168
 13  ω     91.00 177.00   0.50    2.80    --  105.75  60.00 -96.65  172
 14  ω     94.00 178.00   0.50    2.80    --  105.75  45.00-180.00  168
 15  ω     91.00 177.00   0.50    2.80    --  105.75  60.00  46.67  172
 16  ω     94.00 178.00   0.50    2.80    --  105.75  45.00 120.00  168
 17  ω     91.00 177.00   0.50    2.80    --  105.75  60.00  75.78  172
 18  ω     92.00 178.00   0.50    2.80    --  105.75  58.00  68.77  172
 19  ω     34.00  68.00   0.50    2.80    --  105.75 -59.00  40.50   68
 20  ω     33.00  64.00   0.50    2.80    --  105.75 -56.00 -24.25   62
 21  ω     34.00  67.00   0.50    2.80    --  105.75 -58.00   0.00   66
 22  ω     34.00  70.00   0.50    2.80    --  105.75 -60.00  68.52   72
 23  ω     34.00  67.00   0.50    2.80    --  105.75 -58.00  97.19   66
 24  ω     33.00  66.00   0.50    2.80    --  105.75 -57.00 136.11   66
 25  ω     34.00  67.00   0.50    2.80    --  105.75 -58.00 169.21   66
 26  ω     33.00  66.00   0.50    2.80    --  105.75 -57.00 105.07   66
 27  ω     34.00  67.00   0.50    2.80    --  105.75 -58.00  25.95   66
 28  ω     33.00  62.00   0.50    2.80    --  105.75 -54.00 -45.20   58
 29  ω     33.00  62.00   0.50    2.80    --  105.75 -54.00 -64.59   58
 30  ω     33.00  62.00   0.50    2.80    --  105.75 -54.00-109.92   58
 31  ω     34.00  68.00   0.50    2.80    --  105.75 -59.00-170.37   68
 32  ω     32.00  58.00   0.50    2.80    --  105.75 -51.00-166.26   52
 33  ω     32.00  59.00   0.50    2.80    --  105.75 -52.00-143.34   54
 34  ω     33.00  66.00   0.50    2.80    --  105.75 -57.00-125.35   66
 35  ω     38.00 124.00   0.50    0.70    --   51.72  57.00   0.00  172
 36  ω     38.00 124.00   0.50    0.70    --   51.72  58.00 141.00  172
 37  ω    -26.00  25.00   0.50    0.70    --  -54.72  19.00  30.00  102
 38  ω    -26.00  25.00   0.50    0.70    --  -54.72  19.00 -90.00  102
 39  ω    -26.00  25.00   0.50    0.70    --  -54.72  19.00-150.00  102
 40  ω    -43.00  22.00   0.50    0.70    --  -54.72  38.00  90.00  130
 41  ω   -132.00 -46.00   0.50    0.70    --  -54.72 -38.00-150.00  172
 42  ω   -127.00 -41.00   0.50    0.70    --  -54.72 -57.00   0.00  172
 43  ω   -132.00 -46.00   0.50    0.70    --  -54.72 -38.00 -90.00  172
 44  ω   -157.00 -71.00   0.50    2.80    --  -84.25 -56.00-152.22  172
 45  ω   -158.00 -72.00   0.50    2.80    --  -84.25 -52.00-115.23  172
 46  ω   -127.00 -84.00   0.50    0.70    --  -54.72 -58.00 129.74   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1445653000
_diffrn_orient_matrix_UB_12      -0.0327763000
_diffrn_orient_matrix_UB_13      -0.0089604000
_diffrn_orient_matrix_UB_21      -0.0653559000
_diffrn_orient_matrix_UB_22      -0.0917753000
_diffrn_orient_matrix_UB_23      -0.0896797000
_diffrn_orient_matrix_UB_31      -0.0122343000
_diffrn_orient_matrix_UB_32      0.1017844000
_diffrn_orient_matrix_UB_33      -0.0837011000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.895
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2838
_reflns_number_total             2850

_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015b)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 1329 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.019(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2850
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0174
_refine_ls_R_factor_gt           0.0174
_refine_ls_restrained_S_all      1.073
_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)+(0.0264P)²+1.4103P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0461
_refine_ls_wR_factor_ref         0.0461
_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 Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.44565(3) 0.22502(3) 0.83024(3) 0.02656(9) Uani 1 1 d . . . . .
Br2 Br 0.83207(4) 0.58083(4) 1.04943(3) 0.03233(11) Uani 1 1 d . . . . .
C1 C 0.5999(3) 0.3765(3) 0.7296(2) 0.0200(6) Uani 1 1 d . . . . .
C2 C 0.5835(3) 0.3438(3) 0.8298(2) 0.0214(6) Uani 1 1 d . . . . .
C3 C 0.6529(3) 0.3997(3) 0.9248(3) 0.0236(6) Uani 1 1 d . . . . .
H3 H 0.638430 0.374540 0.990330 0.028 Uiso 1 1 calc R . . . .
C4 C 0.7447(3) 0.4941(3) 0.9221(3) 0.0247(7) Uani 1 1 d . . . . .
C5 C 0.7682(3) 0.5290(3) 0.8276(3) 0.0229(6) Uani 1 1 d . . . . .
H5 H 0.832222 0.592497 0.827298 0.027 Uiso 1 1 calc R . . . .
C6 C 0.6976(3) 0.4708(3) 0.7313(3) 0.0216(6) Uani 1 1 d . . . . .
C7 C 0.7339(3) 0.5086(3) 0.6366(3) 0.0218(6) Uani 1 1 d . . . . .
H7 H 0.809679 0.563375 0.647396 0.026 Uiso 1 1 calc R . . . .
C8 C 0.7472(3) 0.5173(3) 0.4602(3) 0.0235(7) Uani 1 1 d . . . . .
H8 H 0.827143 0.569337 0.499075 0.028 Uiso 1 1 calc R . . . .
C9 C 0.6523(3) 0.5967(3) 0.3745(2) 0.0223(6) Uani 1 1 d . . . . .
C10 C 0.5915(4) 0.6976(4) 0.4071(3) 0.0315(8) Uani 1 1 d . . . . .
H10 H 0.609101 0.714095 0.481207 0.038 Uiso 1 1 calc R . . . .
C11 C 0.5053(5) 0.7749(4) 0.3328(4) 0.0377(9) Uani 1 1 d . . . . .
H11 H 0.461175 0.841812 0.355982 0.045 Uiso 1 1 calc R . . . .
C12 C 0.4839(4) 0.7536(4) 0.2243(3) 0.0371(9) Uani 1 1 d . . . . .
H12 H 0.425682 0.806286 0.172991 0.045 Uiso 1 1 calc R . . . .
C13 C 0.5478(4) 0.6555(4) 0.1914(3) 0.0307(8) Uani 1 1 d . . . . .
H13 H 0.534767 0.642144 0.117382 0.037 Uiso 1 1 calc R . . . .
C14 C 0.6309(3) 0.5761(4) 0.2659(3) 0.0259(6) Uani 1 1 d . . . . .
H14 H 0.673042 0.508005 0.242542 0.031 Uiso 1 1 calc R . . . .
C15 C 0.8058(4) 0.4061(4) 0.4185(3) 0.0285(7) Uani 1 1 d . . . . .
H15A H 0.868613 0.362438 0.478482 0.043 Uiso 1 1 calc GR . . . .
H15B H 0.856414 0.432593 0.368680 0.043 Uiso 1 1 calc GR . . . .
H15C H 0.730173 0.351699 0.381586 0.043 Uiso 1 1 calc GR . . . .
N1 N 0.6755(3) 0.4766(3) 0.5399(2) 0.0214(5) Uani 1 1 d . . . . .
Ni1 Ni 0.500000 0.37803(7) 0.500000 0.02133(17) Uani 1 2 d S T P . .
O1 O 0.5279(2) 0.3221(2) 0.64276(19) 0.0233(5) 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 C2 1.906(3) . ?
Br2 C4 1.899(3) . ?
C1 C2 1.412(4) . ?
C1 C6 1.423(5) . ?
C1 O1 1.303(4) . ?
C2 C3 1.381(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.394(5) . ?
C4 C5 1.376(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.408(5) . ?
C6 C7 1.448(4) . ?
C7 H7 0.9500 . ?
C7 N1 1.281(4) . ?
C8 H8 1.0000 . ?
C8 C9 1.521(5) . ?
C8 C15 1.518(5) . ?
C8 N1 1.497(4) . ?
C9 C10 1.388(5) . ?
C9 C14 1.392(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.392(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.392(5) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N1 Ni1 2.012(3) . ?
Ni1 O1 1.906(2) . ?
Ni1 O1 1.906(2) 2_656 ?

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
C2 C1 C6 115.7(3) . . ?
O1 C1 C2 120.5(3) . . ?
O1 C1 C6 123.8(3) . . ?
C1 C2 Br1 117.0(2) . . ?
C3 C2 Br1 118.8(2) . . ?
C3 C2 C1 123.9(3) . . ?
C2 C3 H3 120.8 . . ?
C2 C3 C4 118.3(3) . . ?
C4 C3 H3 120.8 . . ?
C3 C4 Br2 119.5(2) . . ?
C5 C4 Br2 119.5(3) . . ?
C5 C4 C3 121.0(3) . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C7 122.5(3) . . ?
C5 C6 C1 120.9(3) . . ?
C5 C6 C7 116.6(3) . . ?
C6 C7 H7 116.3 . . ?
N1 C7 C6 127.4(3) . . ?
N1 C7 H7 116.3 . . ?
C9 C8 H8 107.3 . . ?
C15 C8 H8 107.3 . . ?
C15 C8 C9 114.9(3) . . ?
N1 C8 H8 107.3 . . ?
N1 C8 C9 110.6(3) . . ?
N1 C8 C15 109.1(3) . . ?
C10 C9 C8 118.0(3) . . ?
C10 C9 C14 119.2(3) . . ?
C14 C9 C8 122.7(3) . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.8(4) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.6(4) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.8(4) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.6(4) . . ?
C14 C13 H13 119.7 . . ?
C9 C14 C13 119.9(3) . . ?
C9 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 N1 C8 115.3(3) . . ?
C7 N1 Ni1 121.7(2) . . ?
C8 N1 Ni1 123.0(2) . . ?
N1 Ni1 N1 115.24(16) 2_656 . ?
O1 Ni1 N1 107.33(11) . 2_656 ?
O1 Ni1 N1 92.61(10) . . ?
O1 Ni1 N1 107.33(11) 2_656 . ?
O1 Ni1 N1 92.61(10) 2_656 2_656 ?
O1 Ni1 O1 142.60(15) . 2_656 ?
C1 O1 Ni1 126.6(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C2 C3 C4 -174.4(2) . . . . ?
Br2 C4 C5 C6 -176.0(2) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C1 C6 C7 N1 9.1(5) . . . . ?
C2 C1 C6 C5 -2.1(5) . . . . ?
C2 C1 C6 C7 175.3(3) . . . . ?
C2 C1 O1 Ni1 163.3(2) . . . . ?
C2 C3 C4 Br2 175.6(3) . . . . ?
C2 C3 C4 C5 -1.5(5) . . . . ?
C3 C4 C5 C6 1.1(5) . . . . ?
C4 C5 C6 C1 0.8(5) . . . . ?
C4 C5 C6 C7 -176.8(3) . . . . ?
C5 C6 C7 N1 -173.4(3) . . . . ?
C6 C1 C2 Br1 176.2(2) . . . . ?
C6 C1 C2 C3 1.7(5) . . . . ?
C6 C1 O1 Ni1 -16.4(5) . . . . ?
C6 C7 N1 C8 -172.2(3) . . . . ?
C6 C7 N1 Ni1 7.6(5) . . . . ?
C8 C9 C10 C11 179.1(3) . . . . ?
C8 C9 C14 C13 -177.0(3) . . . . ?
C9 C8 N1 C7 -121.0(3) . . . . ?
C9 C8 N1 Ni1 59.3(3) . . . . ?
C9 C10 C11 C12 -2.6(6) . . . . ?
C10 C9 C14 C13 -0.9(5) . . . . ?
C10 C11 C12 C13 0.5(6) . . . . ?
C11 C12 C13 C14 1.4(6) . . . . ?
C12 C13 C14 C9 -1.2(5) . . . . ?
C14 C9 C10 C11 2.8(5) . . . . ?
C15 C8 C9 C10 177.9(3) . . . . ?
C15 C8 C9 C14 -5.9(5) . . . . ?
C15 C8 N1 C7 111.6(3) . . . . ?
C15 C8 N1 Ni1 -68.1(3) . . . . ?
N1 C8 C9 C10 53.8(4) . . . . ?
N1 C8 C9 C14 -130.0(3) . . . . ?
O1 C1 C2 Br1 -3.4(4) . . . . ?
O1 C1 C2 C3 -177.9(3) . . . . ?
O1 C1 C6 C5 177.5(3) . . . . ?
O1 C1 C6 C7 -5.0(5) . . . . ?


####################################################################### 
# 
# 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_hadi1311
_database_code_depnum_ccdc_archive 'CCDC 2000651'
loop_
_audit_author_name
_audit_author_address
'Olivier Blacque'
;University of Zurich
Switzerland
;
_audit_update_record             
;
2020-05-02 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
;

_audit_creation_date             2019-11-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H24 Cl4 N2 Ni O2'
_chemical_formula_sum            'C30 H24 Cl4 N2 Ni O2'
_chemical_formula_weight         645.02
_chemical_absolute_configuration ad
_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 0.0033 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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           5
_space_group_name_H-M_alt        'I 1 2 1'
_space_group_name_Hall           'I 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   9.9679(2)
_cell_length_b                   10.8655(2)
_cell_length_c                   12.8831(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.713(3)
_cell_angle_gamma                90
_cell_volume                     1336.37(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8387
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      29.1640
_cell_measurement_theta_min      3.0470
_shelx_estimated_absorpt_T_max   0.944
_shelx_estimated_absorpt_T_min   0.776
_exptl_absorpt_coefficient_mu    1.159
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_correction_T_min  0.816
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             660
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 1 0.0279
1 0 -1 0.0259
-1 5 -5 0.0729
0 -1 1 0.0913
2 5 4 0.1209
-1 -1 0 0.0691
5 1 -2 0.0547
-2 -2 5 0.0727
0 -5 1 0.1045
1 -5 -5 0.0844

_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.05

_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13534
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         2.498
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00  31.50   0.70   10.00    --    9.77 -37.00 150.00  135
  2  ω    -77.00  95.20   0.70   10.00    --    9.77   0.00-150.00  246
  3  ω    -69.00  46.50   0.70   10.00    --    9.77 -19.00 -30.00  165
  4  ω    -20.00  29.00   0.70   10.00    --  -10.39 -99.00  90.00   70
  5  ω    -13.00  82.20   0.70   10.00    --    9.77  37.00 -30.00  136
  6  ω    -20.00  50.00   0.70   10.00    --    9.77 -99.00 -60.00  100
  7  ω    -20.00  50.00   0.70   10.00    --    9.77 -99.00 120.00  100
  8  ω    -20.00  29.00   0.70   10.00    --  -10.39 -99.00 150.00   70
  9  ω    -20.00  29.00   0.70   10.00    --  -10.39 -99.00 -30.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0417264000
_diffrn_orient_matrix_UB_12      0.0414996000
_diffrn_orient_matrix_UB_13      0.0198169000
_diffrn_orient_matrix_UB_21      -0.0540123000
_diffrn_orient_matrix_UB_22      -0.0048240000
_diffrn_orient_matrix_UB_23      -0.0496688000
_diffrn_orient_matrix_UB_31      -0.0294644000
_diffrn_orient_matrix_UB_32      -0.0500999000
_diffrn_orient_matrix_UB_33      0.0211472000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.894
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2628
_reflns_number_total             2722

_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Flack x determined using 1186 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.024(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2722
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0256
_refine_ls_restrained_S_all      1.054
_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)+(0.0420P)²+0.4587P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0647
_refine_ls_wR_factor_ref         0.0659
_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 Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
C1 C 0.3991(3) 0.3732(4) 0.2675(2) 0.0213(6) Uani 1 1 d . . . . .
C2 C 0.4154(3) 0.3408(3) 0.1654(3) 0.0221(7) Uani 1 1 d . . . . .
C3 C 0.3450(3) 0.3972(3) 0.0699(3) 0.0255(7) Uani 1 1 d . . . . .
H3 H 0.359526 0.372088 0.003365 0.031 Uiso 1 1 calc R . . . .
C4 C 0.2522(4) 0.4917(3) 0.0725(3) 0.0261(7) Uani 1 1 d . . . . .
C5 C 0.2286(3) 0.5267(3) 0.1682(3) 0.0245(7) Uani 1 1 d . . . . .
H5 H 0.163874 0.590670 0.168664 0.029 Uiso 1 1 calc R . . . .
C6 C 0.3006(3) 0.4677(3) 0.2655(3) 0.0217(6) Uani 1 1 d . . . . .
C7 C 0.2630(3) 0.5049(3) 0.3612(3) 0.0217(6) Uani 1 1 d . . . . .
H7 H 0.186020 0.559888 0.350163 0.026 Uiso 1 1 calc R . . . .
C8 C 0.2493(3) 0.5114(3) 0.5408(3) 0.0239(7) Uani 1 1 d . . . . .
H8 H 0.166494 0.561913 0.501229 0.029 Uiso 1 1 calc R . . . .
C9 C 0.3441(3) 0.5929(3) 0.6272(3) 0.0231(7) Uani 1 1 d . . . . .
C10 C 0.4076(4) 0.6931(3) 0.5939(3) 0.0305(8) Uani 1 1 d . . . . .
H10 H 0.391213 0.708204 0.518625 0.037 Uiso 1 1 calc R . . . .
C11 C 0.4942(4) 0.7710(3) 0.6681(3) 0.0358(9) Uani 1 1 d . . . . .
H11 H 0.537959 0.838503 0.644054 0.043 Uiso 1 1 calc R . . . .
C12 C 0.5171(4) 0.7502(4) 0.7781(3) 0.0361(9) Uani 1 1 d . . . . .
H12 H 0.577725 0.802714 0.829826 0.043 Uiso 1 1 calc R . . . .
C13 C 0.4515(4) 0.6533(3) 0.8119(3) 0.0316(8) Uani 1 1 d . . . . .
H13 H 0.464845 0.640735 0.887189 0.038 Uiso 1 1 calc R . . . .
C14 C 0.3659(4) 0.5736(3) 0.7374(3) 0.0266(7) Uani 1 1 d . . . . .
H14 H 0.322433 0.506116 0.761707 0.032 Uiso 1 1 calc R . . . .
C15 C 0.1940(4) 0.3975(3) 0.5845(3) 0.0305(8) Uani 1 1 d . . . . .
H15A H 0.132466 0.351175 0.524159 0.046 Uiso 1 1 calc GR . . . .
H15B H 0.141205 0.422888 0.634412 0.046 Uiso 1 1 calc GR . . . .
H15C H 0.272851 0.345448 0.623108 0.046 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.54050(9) 0.22820(8) 0.16427(7) 0.0288(2) Uani 1 1 d . . . . .
Cl2 Cl 0.16894(10) 0.57052(9) -0.04675(7) 0.0364(2) Uani 1 1 d . . . . .
N1 N 0.3226(3) 0.4718(2) 0.4601(2) 0.0208(6) Uani 1 1 d . . . . .
Ni1 Ni 0.500000 0.37422(4) 0.500000 0.02074(15) Uani 1 2 d S T P . .
O1 O 0.4710(2) 0.3175(2) 0.35489(18) 0.0233(5) 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
C1 C2 1.415(4) . ?
C1 C6 1.416(5) . ?
C1 O1 1.298(4) . ?
C2 C3 1.373(5) . ?
C2 Cl1 1.750(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(5) . ?
C4 C5 1.373(5) . ?
C4 Cl2 1.746(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.408(5) . ?
C6 C7 1.445(4) . ?
C7 H7 0.9500 . ?
C7 N1 1.293(4) . ?
C8 H8 1.0000 . ?
C8 C9 1.521(5) . ?
C8 C15 1.526(5) . ?
C8 N1 1.495(4) . ?
C9 C10 1.388(5) . ?
C9 C14 1.389(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.379(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.388(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.374(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.389(5) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N1 Ni1 1.998(3) . ?
Ni1 O1 1.910(2) . ?
Ni1 O1 1.910(2) 2_656 ?

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
C2 C1 C6 115.4(3) . . ?
O1 C1 C2 120.5(3) . . ?
O1 C1 C6 124.1(3) . . ?
C1 C2 Cl1 117.0(2) . . ?
C3 C2 C1 123.8(3) . . ?
C3 C2 Cl1 119.1(2) . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.8(3) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 Cl2 119.5(2) . . ?
C5 C4 C3 120.9(3) . . ?
C5 C4 Cl2 119.6(3) . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 119.9(3) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C7 122.5(3) . . ?
C5 C6 C1 121.2(3) . . ?
C5 C6 C7 116.2(3) . . ?
C6 C7 H7 116.4 . . ?
N1 C7 C6 127.2(3) . . ?
N1 C7 H7 116.4 . . ?
C9 C8 H8 107.5 . . ?
C9 C8 C15 114.6(3) . . ?
C15 C8 H8 107.5 . . ?
N1 C8 H8 107.5 . . ?
N1 C8 C9 110.5(3) . . ?
N1 C8 C15 108.9(3) . . ?
C10 C9 C8 118.3(3) . . ?
C10 C9 C14 118.9(3) . . ?
C14 C9 C8 122.8(3) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.2(3) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.7(4) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.6(3) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.8(3) . . ?
C14 C13 H13 119.6 . . ?
C9 C14 H14 120.1 . . ?
C13 C14 C9 119.8(3) . . ?
C13 C14 H14 120.1 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 N1 C8 115.3(3) . . ?
C7 N1 Ni1 121.5(2) . . ?
C8 N1 Ni1 123.2(2) . . ?
N1 Ni1 N1 115.92(15) 2_656 . ?
O1 Ni1 N1 107.24(10) . 2_656 ?
O1 Ni1 N1 92.62(10) . . ?
O1 Ni1 N1 107.24(10) 2_656 . ?
O1 Ni1 N1 92.62(10) 2_656 2_656 ?
O1 Ni1 O1 142.37(14) . 2_656 ?
C1 O1 Ni1 126.1(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 0.0(5) . . . . ?
C1 C6 C7 N1 9.3(5) . . . . ?
C2 C1 C6 C5 -2.1(4) . . . . ?
C2 C1 C6 C7 174.9(3) . . . . ?
C2 C1 O1 Ni1 162.9(2) . . . . ?
C2 C3 C4 C5 -1.4(5) . . . . ?
C2 C3 C4 Cl2 176.4(3) . . . . ?
C3 C4 C5 C6 0.9(5) . . . . ?
C4 C5 C6 C1 0.9(5) . . . . ?
C4 C5 C6 C7 -176.3(3) . . . . ?
C5 C6 C7 N1 -173.6(3) . . . . ?
C6 C1 C2 C3 1.7(5) . . . . ?
C6 C1 C2 Cl1 177.9(2) . . . . ?
C6 C1 O1 Ni1 -17.5(4) . . . . ?
C6 C7 N1 C8 -172.0(3) . . . . ?
C6 C7 N1 Ni1 7.9(4) . . . . ?
C8 C9 C10 C11 179.7(3) . . . . ?
C8 C9 C14 C13 -178.6(3) . . . . ?
C9 C8 N1 C7 -119.9(3) . . . . ?
C9 C8 N1 Ni1 60.2(3) . . . . ?
C9 C10 C11 C12 -0.9(6) . . . . ?
C10 C9 C14 C13 -0.7(5) . . . . ?
C10 C11 C12 C13 -1.0(6) . . . . ?
C11 C12 C13 C14 2.0(5) . . . . ?
C12 C13 C14 C9 -1.1(5) . . . . ?
C14 C9 C10 C11 1.7(5) . . . . ?
C15 C8 C9 C10 175.0(3) . . . . ?
C15 C8 C9 C14 -7.1(4) . . . . ?
C15 C8 N1 C7 113.4(3) . . . . ?
C15 C8 N1 Ni1 -66.5(3) . . . . ?
Cl1 C2 C3 C4 -176.1(2) . . . . ?
Cl2 C4 C5 C6 -176.9(2) . . . . ?
N1 C8 C9 C10 51.5(4) . . . . ?
N1 C8 C9 C14 -130.6(3) . . . . ?
O1 C1 C2 C3 -178.7(3) . . . . ?
O1 C1 C2 Cl1 -2.5(4) . . . . ?
O1 C1 C6 C5 178.3(3) . . . . ?
O1 C1 C6 C7 -4.7(5) . . . . ?

