# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_az032b_150k_0m
_database_code_depnum_ccdc_archive 'CCDC 2215529'
loop_
_audit_author_name
_audit_author_address
'Anton Dmitrienko'
;University of Windsor
Canada
;
_audit_update_record             
;
2022-10-26 deposited with the CCDC.	2023-02-07 downloaded from the CCDC.
;
_audit_creation_date             2021-02-12
_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         'C15 H28.36 B0.84 Br0.16 N Ni O P'
_chemical_formula_sum            'C15 H28.36 B0.84 Br0.16 N Ni O P'
_chemical_formula_weight         350.29
_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'
B B 0.0013 0.0007 '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'
P P 0.1023 0.0942 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3802(11)
_cell_length_b                   9.4495(11)
_cell_length_c                   10.9044(13)
_cell_angle_alpha                66.939(4)
_cell_angle_beta                 78.797(4)
_cell_angle_gamma                75.715(4)
_cell_volume                     856.63(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9888
_cell_measurement_temperature    150.0(1)
_cell_measurement_theta_max      28.517
_cell_measurement_theta_min      2.254
_shelx_estimated_absorpt_T_max   0.880
_shelx_estimated_absorpt_T_min   0.651
_exptl_absorpt_coefficient_mu    1.594
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.1236 before and 0.0762 after correction. The Ratio of minimum to maximum transmission is 0.6438. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear reddish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Diethyl ether'
_exptl_crystal_size_max          0.295
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.082
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21084
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.557
_diffrn_reflns_theta_min         2.042
_diffrn_ambient_temperature      150.0(1)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4017
_reflns_number_total             4327
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.785
_refine_diff_density_min         -0.605
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         4327
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0278
_refine_ls_restrained_S_all      1.047
_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)+(0.0297P)²+0.5134P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0690
_refine_ls_wR_factor_ref         0.0710
_refine_special_details          
'Two molecules are co-crystallized. Occupancy of Br and BH4 unit were refined to 0.160 and 0.839 respectively.,Substitutional disorder of BH4 and Br (0.84:0.16)'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H1D-B1
 1.2 with sigma of 0.02
 H1F-B1
 1.2 with sigma of 0.02
 B1-H1E
 1.2 with sigma of 0.02
 B1-H1G
 1.2 with sigma of 0.02
 H1F-B1 \\sim B1-H1D
 with sigma of 0.02
 H1E-B1 \\sim B1-H1G
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(B1) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
4. Others
 Sof(H1D)=Sof(H1E)=Sof(H1F)=Sof(H1G)=Sof(B1)=1-FVAR(1)
 Sof(Br1)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13)
5.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
5.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7)
5.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C),
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.1701(8) 1.0049(5) 0.6996(5) 0.0286(13) Uani 0.1613(11) 1 d . . P A 2
H1D H 0.098(2) 0.911(3) 0.745(2) 0.025(6) Uiso 0.8387(11) 1 d D . P A 1
H1E H 0.178(3) 1.054(3) 0.5775(18) 0.043(8) Uiso 0.8387(11) 1 d D . P A 1
H1F H 0.302(2) 0.917(3) 0.724(3) 0.038(7) Uiso 0.8387(11) 1 d D . P A 1
H1G H 0.160(3) 1.086(3) 0.752(2) 0.037(7) Uiso 0.8387(11) 1 d D . P A 1
Ni1 Ni 0.24023(2) 0.73709(2) 0.80380(2) 0.01340(6) Uani 1 1 d . . . . .
P002 P 0.26785(4) 0.68057(4) 0.62916(4) 0.01417(8) Uani 1 1 d . . . . .
O1 O 0.30620(12) 0.48630(12) 0.67665(10) 0.0186(2) Uani 1 1 d . . . . .
N1 N 0.19844(13) 0.72609(14) 0.99603(12) 0.0151(2) Uani 1 1 d . . . . .
C1 C 0.22466(19) 0.85991(18) 1.02204(16) 0.0227(3) Uani 1 1 d . . . . .
H1A H 0.329802 0.866279 0.999154 0.034 Uiso 1 1 calc GR . . . .
H1B H 0.196165 0.844571 1.117087 0.034 Uiso 1 1 calc GR . . . .
H1C H 0.165344 0.957280 0.967061 0.034 Uiso 1 1 calc GR . . . .
C2 C 0.03812(16) 0.71780(19) 1.03363(16) 0.0210(3) Uani 1 1 d . . . . .
H2A H -0.020794 0.810071 0.972454 0.031 Uiso 1 1 calc GR . . . .
H2B H 0.009116 0.715051 1.125745 0.031 Uiso 1 1 calc GR . . . .
H2C H 0.020793 0.622842 1.027382 0.031 Uiso 1 1 calc GR . . . .
C3 C 0.28833(16) 0.57762(16) 1.08237(15) 0.0170(3) Uani 1 1 d . . . . .
H3A H 0.237335 0.541718 1.174529 0.020 Uiso 1 1 calc R . . . .
H3B H 0.386528 0.595529 1.086816 0.020 Uiso 1 1 calc R . . . .
C4 C 0.30583(15) 0.45658(16) 1.02035(14) 0.0151(3) Uani 1 1 d . . . . .
C5 C 0.33798(16) 0.29442(17) 1.08711(15) 0.0192(3) Uani 1 1 d . . . . .
H5 H 0.346200 0.251557 1.180682 0.023 Uiso 1 1 calc R . . . .
C6 C 0.35788(17) 0.19611(17) 1.01505(16) 0.0199(3) Uani 1 1 d . . . . .
H6 H 0.378826 0.085863 1.060748 0.024 Uiso 1 1 calc R . . . .
C7 C 0.34773(16) 0.25594(17) 0.87742(16) 0.0186(3) Uani 1 1 d . . . . .
H7 H 0.362034 0.188473 0.828674 0.022 Uiso 1 1 calc R . . . .
C8 C 0.31594(15) 0.41779(16) 0.81411(14) 0.0151(3) Uani 1 1 d . . . . .
C9 C 0.29322(15) 0.51970(16) 0.88291(14) 0.0142(3) Uani 1 1 d . . . . .
C10 C 0.42174(16) 0.73104(17) 0.49797(15) 0.0183(3) Uani 1 1 d . . . . .
H10 H 0.435852 0.662865 0.444199 0.022 Uiso 1 1 calc R . . . .
C11 C 0.56384(18) 0.6935(2) 0.56315(19) 0.0283(4) Uani 1 1 d . . . . .
H11A H 0.580151 0.583827 0.623945 0.042 Uiso 1 1 calc GR . . . .
H11B H 0.554442 0.761713 0.613846 0.042 Uiso 1 1 calc GR . . . .
H11C H 0.647877 0.711080 0.493368 0.042 Uiso 1 1 calc GR . . . .
C12 C 0.39180(19) 0.9022(2) 0.40171(17) 0.0277(4) Uani 1 1 d . . . . .
H12A H 0.306981 0.919777 0.353925 0.041 Uiso 1 1 calc GR . . . .
H12B H 0.479277 0.924514 0.336895 0.041 Uiso 1 1 calc GR . . . .
H12C H 0.370042 0.971718 0.452871 0.041 Uiso 1 1 calc GR . . . .
C13 C 0.10150(16) 0.73169(17) 0.54492(15) 0.0176(3) Uani 1 1 d . . . . .
H13 H 0.077210 0.848384 0.502036 0.021 Uiso 1 1 calc R . . . .
C14 C -0.02822(18) 0.6781(2) 0.64930(18) 0.0293(4) Uani 1 1 d . . . . .
H14A H -0.006250 0.563961 0.693923 0.044 Uiso 1 1 calc GR . . . .
H14B H -0.118173 0.708479 0.604781 0.044 Uiso 1 1 calc GR . . . .
H14C H -0.043234 0.727524 0.715969 0.044 Uiso 1 1 calc GR . . . .
C15 C 0.12331(19) 0.6633(2) 0.43484(17) 0.0264(3) Uani 1 1 d . . . . .
H15A H 0.205437 0.700818 0.368440 0.040 Uiso 1 1 calc GR . . . .
H15B H 0.032558 0.696594 0.390992 0.040 Uiso 1 1 calc GR . . . .
H15C H 0.145890 0.548673 0.474680 0.040 Uiso 1 1 calc GR . . . .
B1 B 0.1844(17) 0.9999(11) 0.6933(13) 0.0222(17) Uani 0.8387(11) 1 d D U P A 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Ni1 2.311(5) . ?
Ni1 P002 2.1250(5) . ?
Ni1 N1 2.0220(13) . ?
Ni1 C9 1.8669(14) . ?
Ni1 B1 2.270(10) . ?
P002 O1 1.6642(11) . ?
P002 C10 1.8332(15) . ?
P002 C13 1.8301(15) . ?
O1 C8 1.3921(17) . ?
N1 C1 1.4838(19) . ?
N1 C2 1.4931(19) . ?
N1 C3 1.5018(18) . ?
C3 C4 1.504(2) . ?
C4 C5 1.397(2) . ?
C4 C9 1.396(2) . ?
C5 C6 1.395(2) . ?
C6 C7 1.395(2) . ?
C7 C8 1.3901(19) . ?
C8 C9 1.392(2) . ?
C10 C11 1.531(2) . ?
C10 C12 1.536(2) . ?
C13 C14 1.532(2) . ?
C13 C15 1.532(2) . ?

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
P002 Ni1 Br1 96.71(14) . . ?
P002 Ni1 B1 94.8(3) . . ?
N1 Ni1 Br1 98.26(15) . . ?
N1 Ni1 P002 162.74(4) . . ?
N1 Ni1 B1 100.5(3) . . ?
C9 Ni1 Br1 177.69(13) . . ?
C9 Ni1 P002 81.34(5) . . ?
C9 Ni1 N1 83.49(6) . . ?
C9 Ni1 B1 175.8(4) . . ?
O1 P002 Ni1 107.73(4) . . ?
O1 P002 C10 100.16(6) . . ?
O1 P002 C13 102.07(6) . . ?
C10 P002 Ni1 121.26(5) . . ?
C13 P002 Ni1 115.70(5) . . ?
C13 P002 C10 107.08(7) . . ?
C8 O1 P002 110.29(9) . . ?
C1 N1 Ni1 116.60(9) . . ?
C1 N1 C2 108.30(11) . . ?
C1 N1 C3 108.84(12) . . ?
C2 N1 Ni1 104.95(9) . . ?
C2 N1 C3 109.00(11) . . ?
C3 N1 Ni1 108.91(9) . . ?
N1 C3 C4 107.54(12) . . ?
C5 C4 C3 125.69(13) . . ?
C9 C4 C3 113.89(12) . . ?
C9 C4 C5 120.37(13) . . ?
C6 C5 C4 119.36(14) . . ?
C5 C6 C7 121.50(13) . . ?
C8 C7 C6 117.64(14) . . ?
O1 C8 C9 116.47(12) . . ?
C7 C8 O1 120.98(13) . . ?
C7 C8 C9 122.55(14) . . ?
C4 C9 Ni1 117.43(10) . . ?
C8 C9 Ni1 123.97(11) . . ?
C8 C9 C4 118.56(13) . . ?
C11 C10 P002 109.33(11) . . ?
C11 C10 C12 111.23(13) . . ?
C12 C10 P002 112.83(10) . . ?
C14 C13 P002 109.33(11) . . ?
C14 C13 C15 110.97(13) . . ?
C15 C13 P002 112.59(10) . . ?

# end Validation Reply Form
_olex2_exptl_crystal_mounting_method 
'on glass microloop covered with paratone oil.'
_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT041_az032b_150k_0m      
;
PROBLEM: Calc. and Reported SumFormula    Strings  Differ     Please Check 
RESPONSE: The sample is represented by two molecules co-crystallized.
The refinement of Br and BH4 occupancies led to the non-integer number
for B, Br and H.
;
_vrf_PLAT077_az032b_150k_0m      
;
PROBLEM: Unitcell Contains Non-integer Number of Atoms ..     Please Check 
RESPONSE: The sample is represented by two molecules co-crystallized.
The refinement of Br and BH4 occupancies led to the non-integer number
for B, Br and H.
;
####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2221354'
loop_
_audit_author_name
_audit_author_address
'Konstantin Lyssenko'
;Chemical Department MSU
Russia
;
_audit_update_record             
;
2022-11-22 deposited with the CCDC.	2023-02-07 downloaded from the CCDC.
;
_audit_creation_date             2021-05-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H28 N Ni O3 P'
_chemical_formula_sum            'C17 H28 N Ni O3 P'
_chemical_formula_weight         384.08
_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'
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'
P P 0.1023 0.0942 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7205(4)
_cell_length_b                   9.0830(5)
_cell_length_c                   14.8641(8)
_cell_angle_alpha                76.7640(10)
_cell_angle_beta                 81.7370(10)
_cell_angle_gamma                66.2490(10)
_cell_volume                     927.17(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3220
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.444
_cell_measurement_theta_min      2.495
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.145
_exptl_absorpt_correction_T_max  0.7784
_exptl_absorpt_correction_T_min  0.5289
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0721 before and 0.0506 after correction.
The Ratio of minimum to maximum transmission is 0.9077.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7757
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.000
_diffrn_reflns_theta_min         2.495
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4148
_reflns_number_total             4790
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.590
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         4790
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0413
_refine_ls_restrained_S_all      1.034
_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)+(0.0436P)²+0.3397P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0956
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C4(H4)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C9(H9A,H9B,H9C), C10(H10A,H10B,
 H10C), C17(H17A,H17B,H17C), C13(H13A,H13B,H13C), C12(H12A,H12B,H12C)
;
_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 0.54152(3) 0.47158(3) 0.27903(2) 0.01464(9) Uani 1 1 d . . . . .
P1 P 0.53652(7) 0.69745(6) 0.20037(3) 0.01684(12) Uani 1 1 d . . . . .
O2 O 0.7085(2) 0.33117(18) 0.19695(10) 0.0204(3) Uani 1 1 d . . . . .
O1 O 0.3756(2) 0.84461(17) 0.25004(10) 0.0195(3) Uani 1 1 d . . . . .
O3 O 0.9388(2) 0.3144(2) 0.27646(13) 0.0386(5) Uani 1 1 d . . . . .
N1 N 0.4748(2) 0.2951(2) 0.36469(12) 0.0161(3) Uani 1 1 d . . . . .
C2 C 0.2925(3) 0.7779(2) 0.32958(14) 0.0171(4) Uani 1 1 d . . . . .
C1 C 0.3636(3) 0.6073(2) 0.35250(13) 0.0154(4) Uani 1 1 d . . . . .
C16 C 0.8834(3) 0.2867(3) 0.21060(15) 0.0208(4) Uani 1 1 d . . . . .
C6 C 0.2891(3) 0.5347(2) 0.43263(14) 0.0168(4) Uani 1 1 d . . . . .
C15 C 0.6334(3) 0.1348(3) 0.38441(15) 0.0221(4) Uani 1 1 d . . . . .
H15A H 0.684694 0.094316 0.326577 0.033 Uiso 1 1 calc R U . . .
H15B H 0.587721 0.056700 0.427113 0.033 Uiso 1 1 calc R U . . .
H15C H 0.732949 0.146740 0.412646 0.033 Uiso 1 1 calc R U . . .
C3 C 0.1478(3) 0.8775(2) 0.38144(14) 0.0187(4) Uani 1 1 d . . . . .
H3 H 0.100683 0.993436 0.363831 0.022 Uiso 1 1 calc R U . . .
C5 C 0.1439(3) 0.6309(3) 0.48679(14) 0.0195(4) Uani 1 1 d . . . . .
H5 H 0.092768 0.580913 0.541314 0.023 Uiso 1 1 calc R U . . .
C7 C 0.3858(3) 0.3515(3) 0.45357(14) 0.0187(4) Uani 1 1 d . . . . .
H7A H 0.484110 0.318051 0.498464 0.022 Uiso 1 1 calc R U . . .
H7B H 0.292598 0.301880 0.480872 0.022 Uiso 1 1 calc R U . . .
C4 C 0.0741(3) 0.8008(3) 0.46043(15) 0.0204(4) Uani 1 1 d . . . . .
H4 H -0.025867 0.865893 0.497160 0.024 Uiso 1 1 calc R U . . .
C14 C 0.3307(3) 0.2775(3) 0.31630(16) 0.0242(5) Uani 1 1 d . . . . .
H14A H 0.217885 0.379594 0.309998 0.036 Uiso 1 1 calc R U . . .
H14B H 0.296054 0.187519 0.352214 0.036 Uiso 1 1 calc R U . . .
H14C H 0.383189 0.253883 0.254757 0.036 Uiso 1 1 calc R U . . .
C8 C 0.7443(3) 0.7487(3) 0.19093(15) 0.0225(4) Uani 1 1 d . . . . .
H8 H 0.847907 0.671461 0.155820 0.027 Uiso 1 1 calc R U . . .
C11 C 0.4479(3) 0.7538(3) 0.08474(15) 0.0272(5) Uani 1 1 d . . . . .
H11 H 0.417821 0.873368 0.061925 0.033 Uiso 1 1 calc R U . . .
C9 C 0.8096(3) 0.7201(3) 0.28798(17) 0.0297(5) Uani 1 1 d . . . . .
H9A H 0.709052 0.792487 0.324491 0.045 Uiso 1 1 calc R U . . .
H9B H 0.924009 0.743663 0.283590 0.045 Uiso 1 1 calc R U . . .
H9C H 0.837446 0.605732 0.318123 0.045 Uiso 1 1 calc R U . . .
C10 C 0.7094(4) 0.9230(3) 0.13850(19) 0.0345(6) Uani 1 1 d . . . . .
H10A H 0.688146 0.931679 0.073727 0.052 Uiso 1 1 calc R U . . .
H10B H 0.820172 0.948424 0.141328 0.052 Uiso 1 1 calc R U . . .
H10C H 0.597576 1.000478 0.166844 0.052 Uiso 1 1 calc R U . . .
C17 C 1.0243(3) 0.1910(3) 0.14280(17) 0.0301(5) Uani 1 1 d . . . . .
H17A H 1.008050 0.088323 0.145978 0.045 Uiso 1 1 calc R U . . .
H17B H 1.153327 0.166648 0.158428 0.045 Uiso 1 1 calc R U . . .
H17C H 1.003053 0.255933 0.079988 0.045 Uiso 1 1 calc R U . . .
C13 C 0.2651(4) 0.7243(3) 0.09160(19) 0.0386(6) Uani 1 1 d . . . . .
H13A H 0.293172 0.606662 0.109897 0.058 Uiso 1 1 calc R U . . .
H13B H 0.208534 0.765530 0.031334 0.058 Uiso 1 1 calc R U . . .
H13C H 0.176025 0.781870 0.137977 0.058 Uiso 1 1 calc R U . . .
C12 C 0.5957(4) 0.6598(3) 0.01714(16) 0.0364(6) Uani 1 1 d . . . . .
H12A H 0.704294 0.692523 0.008323 0.055 Uiso 1 1 calc R U . . .
H12B H 0.539974 0.684304 -0.042422 0.055 Uiso 1 1 calc R U . . .
H12C H 0.637909 0.541955 0.042022 0.055 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 P1 2.1043(6) . ?
Ni1 O2 1.9270(14) . ?
Ni1 N1 1.9997(17) . ?
Ni1 C1 1.8493(18) . ?
P1 O1 1.6510(14) . ?
P1 C8 1.822(2) . ?
P1 C11 1.827(2) . ?
O2 C16 1.276(2) . ?
O1 C2 1.394(2) . ?
O3 C16 1.235(3) . ?
N1 C15 1.475(2) . ?
N1 C7 1.499(2) . ?
N1 C14 1.485(3) . ?
C2 C1 1.395(3) . ?
C2 C3 1.385(3) . ?
C1 C6 1.390(3) . ?
C16 C17 1.510(3) . ?
C6 C5 1.394(3) . ?
C6 C7 1.501(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C3 H3 0.9500 . ?
C3 C4 1.393(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.393(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C4 H4 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C8 H8 1.0000 . ?
C8 C9 1.528(3) . ?
C8 C10 1.529(3) . ?
C11 H11 1.0000 . ?
C11 C13 1.524(4) . ?
C11 C12 1.523(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
O2 Ni1 P1 98.45(5) . . ?
O2 Ni1 N1 95.04(6) . . ?
N1 Ni1 P1 164.34(5) . . ?
C1 Ni1 P1 81.75(7) . . ?
C1 Ni1 O2 174.94(7) . . ?
C1 Ni1 N1 84.11(8) . . ?
O1 P1 Ni1 107.99(6) . . ?
O1 P1 C8 101.75(9) . . ?
O1 P1 C11 100.79(9) . . ?
C8 P1 Ni1 120.00(7) . . ?
C8 P1 C11 107.47(11) . . ?
C11 P1 Ni1 116.12(8) . . ?
C16 O2 Ni1 112.97(13) . . ?
C2 O1 P1 110.29(12) . . ?
C15 N1 Ni1 115.27(13) . . ?
C15 N1 C7 109.75(16) . . ?
C15 N1 C14 108.93(16) . . ?
C7 N1 Ni1 109.33(12) . . ?
C14 N1 Ni1 104.26(13) . . ?
C14 N1 C7 109.05(16) . . ?
O1 C2 C1 115.95(17) . . ?
C3 C2 O1 121.05(18) . . ?
C3 C2 C1 123.00(19) . . ?
C2 C1 Ni1 123.79(16) . . ?
C6 C1 Ni1 117.91(15) . . ?
C6 C1 C2 118.20(17) . . ?
O2 C16 C17 116.34(18) . . ?
O3 C16 O2 123.32(19) . . ?
O3 C16 C17 120.32(19) . . ?
C1 C6 C5 120.44(18) . . ?
C1 C6 C7 113.33(17) . . ?
C5 C6 C7 126.18(19) . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C2 C3 H3 121.3 . . ?
C2 C3 C4 117.33(19) . . ?
C4 C3 H3 121.3 . . ?
C6 C5 H5 120.2 . . ?
C4 C5 C6 119.54(19) . . ?
C4 C5 H5 120.2 . . ?
N1 C7 C6 108.03(17) . . ?
N1 C7 H7A 110.1 . . ?
N1 C7 H7B 110.1 . . ?
C6 C7 H7A 110.1 . . ?
C6 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
C3 C4 C5 121.47(18) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
P1 C8 H8 107.8 . . ?
C9 C8 P1 108.77(16) . . ?
C9 C8 H8 107.8 . . ?
C9 C8 C10 111.8(2) . . ?
C10 C8 P1 112.77(16) . . ?
C10 C8 H8 107.8 . . ?
P1 C11 H11 108.3 . . ?
C13 C11 P1 108.70(17) . . ?
C13 C11 H11 108.3 . . ?
C12 C11 P1 111.40(16) . . ?
C12 C11 H11 108.3 . . ?
C12 C11 C13 111.7(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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 P1 O1 C2 0.94(14) . . . . ?
Ni1 P1 C8 C9 -50.34(17) . . . . ?
Ni1 P1 C8 C10 -174.90(14) . . . . ?
Ni1 P1 C11 C13 46.68(18) . . . . ?
Ni1 P1 C11 C12 -76.87(19) . . . . ?
Ni1 O2 C16 O3 8.2(3) . . . . ?
Ni1 O2 C16 C17 -173.85(15) . . . . ?
Ni1 N1 C7 C6 28.61(19) . . . . ?
Ni1 C1 C6 C5 -174.90(15) . . . . ?
Ni1 C1 C6 C7 7.5(2) . . . . ?
P1 Ni1 C1 C2 4.70(16) . . . . ?
P1 Ni1 C1 C6 -178.98(16) . . . . ?
P1 O1 C2 C1 2.3(2) . . . . ?
P1 O1 C2 C3 -177.54(16) . . . . ?
O1 P1 C8 C9 68.64(16) . . . . ?
O1 P1 C8 C10 -55.92(18) . . . . ?
O1 P1 C11 C13 -69.65(17) . . . . ?
O1 P1 C11 C12 166.80(17) . . . . ?
O1 C2 C1 Ni1 -5.4(3) . . . . ?
O1 C2 C1 C6 178.26(17) . . . . ?
O1 C2 C3 C4 -179.32(18) . . . . ?
N1 Ni1 C1 C2 -168.56(18) . . . . ?
N1 Ni1 C1 C6 7.77(16) . . . . ?
C2 C1 C6 C5 1.6(3) . . . . ?
C2 C1 C6 C7 -175.95(17) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C1 C6 C5 C4 -0.3(3) . . . . ?
C1 C6 C7 N1 -23.9(2) . . . . ?
C6 C5 C4 C3 -0.7(3) . . . . ?
C15 N1 C7 C6 155.95(17) . . . . ?
C3 C2 C1 Ni1 174.37(16) . . . . ?
C3 C2 C1 C6 -1.9(3) . . . . ?
C5 C6 C7 N1 158.69(19) . . . . ?
C7 C6 C5 C4 176.9(2) . . . . ?
C14 N1 C7 C6 -84.8(2) . . . . ?
C8 P1 O1 C2 -126.25(14) . . . . ?
C8 P1 C11 C13 -175.75(16) . . . . ?
C8 P1 C11 C12 60.7(2) . . . . ?
C11 P1 O1 C2 123.15(15) . . . . ?
C11 P1 C8 C9 174.06(15) . . . . ?
C11 P1 C8 C10 49.50(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_sm176_150k_0m
_database_code_depnum_ccdc_archive 'CCDC 2215530'
loop_
_audit_author_name
_audit_author_address
'Anton Dmitrienko'
;University of Windsor
Canada
;
_audit_update_record             
;
2022-10-26 deposited with the CCDC.	2023-02-07 downloaded from the CCDC.
;
_audit_creation_date             2021-04-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
ms19za@brocku.ca
andrey.khalimon@nu.edu.kz
ad16bk@brocku.ca
mpilkington@brocku.ca
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15.9 H27.71 Br0.1 N Ni O P'
_chemical_formula_sum            'C15.90 H27.72 Br0.11 N Ni O P'
_chemical_formula_weight         347.03
_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'
P P 0.1023 0.0942 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3433(10)
_cell_length_b                   9.4438(10)
_cell_length_c                   10.8402(11)
_cell_angle_alpha                66.371(3)
_cell_angle_beta                 78.720(3)
_cell_angle_gamma                75.511(3)
_cell_volume                     843.52(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9961
_cell_measurement_temperature    149.99
_cell_measurement_theta_max      28.560
_cell_measurement_theta_min      2.518
_shelx_estimated_absorpt_T_max   0.730
_shelx_estimated_absorpt_T_min   0.431
_exptl_absorpt_coefficient_mu    1.490
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6324
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1031 before and 0.0686 after correction.
The Ratio of minimum to maximum transmission is 0.8481.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       shard
_exptl_crystal_F_000             370
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Diethyl ether'
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.225
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16798
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.560
_diffrn_reflns_theta_min         2.063
_diffrn_ambient_temperature      149.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.58
_diffrn_source_power             0.029
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3853
_reflns_number_total             4231
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         4231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0288
_refine_ls_restrained_S_all      1.072
_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)+(0.0186P)²+0.7057P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0685
_refine_ls_wR_factor_ref         0.0717
_refine_special_details          
'Substitutional disorder of CH3 and Br (0.91:0.09)'
_olex2_refinement_description    
;
1. Others
 Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=FVAR(1)
2.a Ternary CH refined with riding coordinates:
 C11(H11), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C3(H3)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C16(H16A,H16B,H16C),
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), 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 0.23713(2) 0.73758(2) 0.79783(2) 0.01356(7) Uani 1 1 d . . . . .
P1 P 0.26593(4) 0.68324(5) 0.62612(4) 0.01383(9) Uani 1 1 d . . . . .
C10 C 0.1668(13) 0.9725(11) 0.7109(10) 0.032(2) Uani 0.905(19) 1 d . . P A 1
H10A H 0.152466 0.999953 0.616257 0.049 Uiso 0.905(19) 1 calc GR . P A 1
H10B H 0.241289 1.027222 0.714477 0.049 Uiso 0.905(19) 1 calc GR . P A 1
H10C H 0.072388 1.004273 0.759742 0.049 Uiso 0.905(19) 1 calc GR . P A 1
O1 O 0.30573(13) 0.48739(13) 0.67288(11) 0.0178(2) Uani 1 1 d . . . . .
N1 N 0.19738(15) 0.72678(16) 0.99201(13) 0.0147(3) Uani 1 1 d . . . . .
C1 C 0.31764(17) 0.41631(18) 0.81191(15) 0.0151(3) Uani 1 1 d . . . . .
C6 C 0.29459(17) 0.51818(18) 0.88024(15) 0.0140(3) Uani 1 1 d . . . . .
C5 C 0.30629(17) 0.45436(19) 1.01895(15) 0.0151(3) Uani 1 1 d . . . . .
C7 C 0.28724(18) 0.57707(19) 1.07987(15) 0.0168(3) Uani 1 1 d . . . . .
H7A H 0.235571 0.541036 1.172754 0.020 Uiso 1 1 calc R . . . .
H7B H 0.385633 0.594888 1.084788 0.020 Uiso 1 1 calc R . . . .
C2 C 0.35057(18) 0.25414(19) 0.87557(16) 0.0182(3) Uani 1 1 d . . . . .
H2 H 0.365777 0.186876 0.826521 0.022 Uiso 1 1 calc R . . . .
C4 C 0.33902(18) 0.2914(2) 1.08715(15) 0.0184(3) Uani 1 1 d . . . . .
H4 H 0.346490 0.247958 1.181817 0.022 Uiso 1 1 calc R . . . .
C3 C 0.36057(19) 0.19322(19) 1.01528(16) 0.0194(3) Uani 1 1 d . . . . .
H3 H 0.382564 0.082361 1.061888 0.023 Uiso 1 1 calc R . . . .
C11 C 0.42024(18) 0.73620(19) 0.49366(15) 0.0174(3) Uani 1 1 d . . . . .
H11 H 0.433143 0.672282 0.436333 0.021 Uiso 1 1 calc R . . . .
C8 C 0.03698(18) 0.7188(2) 1.02883(17) 0.0210(3) Uani 1 1 d . . . . .
H8A H -0.021939 0.812082 0.966604 0.031 Uiso 1 1 calc GR . . . .
H8B H 0.007292 0.715191 1.121739 0.031 Uiso 1 1 calc GR . . . .
H8C H 0.019841 0.623862 1.022424 0.031 Uiso 1 1 calc GR . . . .
C14 C 0.10092(18) 0.73550(19) 0.53834(15) 0.0176(3) Uani 1 1 d . . . . .
H14 H 0.080063 0.852558 0.491010 0.021 Uiso 1 1 calc R . . . .
C9 C 0.2238(2) 0.8605(2) 1.01649(17) 0.0223(3) Uani 1 1 d . . . . .
H9A H 0.328736 0.868991 0.989966 0.033 Uiso 1 1 calc GR . . . .
H9B H 0.198932 0.843353 1.112883 0.033 Uiso 1 1 calc GR . . . .
H9C H 0.161404 0.957963 0.962871 0.033 Uiso 1 1 calc GR . . . .
C16 C 0.1202(2) 0.6630(2) 0.43158(18) 0.0265(4) Uani 1 1 d . . . . .
H16A H 0.203082 0.697777 0.363590 0.040 Uiso 1 1 calc GR . . . .
H16B H 0.028726 0.696854 0.387619 0.040 Uiso 1 1 calc GR . . . .
H16C H 0.141199 0.547960 0.475000 0.040 Uiso 1 1 calc GR . . . .
C12 C 0.3886(2) 0.9108(2) 0.40241(18) 0.0274(4) Uani 1 1 d . . . . .
H12A H 0.303700 0.931638 0.352857 0.041 Uiso 1 1 calc GR . . . .
H12B H 0.476270 0.937081 0.337858 0.041 Uiso 1 1 calc GR . . . .
H12C H 0.365644 0.975232 0.458133 0.041 Uiso 1 1 calc GR . . . .
C13 C 0.5629(2) 0.6938(2) 0.56027(19) 0.0266(4) Uani 1 1 d . . . . .
H13A H 0.553418 0.757531 0.614918 0.040 Uiso 1 1 calc GR . . . .
H13B H 0.647117 0.714619 0.490065 0.040 Uiso 1 1 calc GR . . . .
H13C H 0.579600 0.581899 0.618533 0.040 Uiso 1 1 calc GR . . . .
C15 C -0.0320(2) 0.6905(3) 0.64308(19) 0.0305(4) Uani 1 1 d . . . . .
H15A H -0.013471 0.576385 0.693194 0.046 Uiso 1 1 calc GR . . . .
H15B H -0.121617 0.721493 0.596935 0.046 Uiso 1 1 calc GR . . . .
H15C H -0.046189 0.744734 0.706230 0.046 Uiso 1 1 calc GR . . . .
Br1 Br 0.1713(11) 1.0001(13) 0.6942(10) 0.0285(12) Uani 0.104(3) 1 d . . . A 2


_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 P1 2.0739(5) . ?
Ni1 C10 2.020(9) . ?
Ni1 N1 2.0298(13) . ?
Ni1 C6 1.8779(16) . ?
Ni1 Br1 2.250(11) . ?
P1 O1 1.6716(12) . ?
P1 C11 1.8347(16) . ?
P1 C14 1.8283(17) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
O1 C1 1.3970(18) . ?
N1 C7 1.500(2) . ?
N1 C8 1.486(2) . ?
N1 C9 1.475(2) . ?
C1 C6 1.388(2) . ?
C1 C2 1.384(2) . ?
C6 C5 1.393(2) . ?
C5 C7 1.508(2) . ?
C5 C4 1.397(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C2 H2 0.9500 . ?
C2 C3 1.401(2) . ?
C4 H4 0.9500 . ?
C4 C3 1.389(2) . ?
C3 H3 0.9500 . ?
C11 H11 1.0000 . ?
C11 C12 1.532(2) . ?
C11 C13 1.528(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C14 H14 1.0000 . ?
C14 C16 1.527(2) . ?
C14 C15 1.529(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
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
P1 Ni1 Br1 96.8(2) . . ?
C10 Ni1 P1 98.2(3) . . ?
C10 Ni1 N1 96.3(3) . . ?
N1 Ni1 P1 163.47(4) . . ?
N1 Ni1 Br1 98.0(2) . . ?
C6 Ni1 P1 81.88(5) . . ?
C6 Ni1 C10 177.7(3) . . ?
C6 Ni1 N1 83.33(6) . . ?
C6 Ni1 Br1 178.6(2) . . ?
O1 P1 Ni1 108.51(4) . . ?
O1 P1 C11 100.00(7) . . ?
O1 P1 C14 101.81(7) . . ?
C11 P1 Ni1 121.26(6) . . ?
C14 P1 Ni1 116.18(5) . . ?
C14 P1 C11 106.18(7) . . ?
Ni1 C10 H10A 109.5 . . ?
Ni1 C10 H10B 109.5 . . ?
Ni1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C1 O1 P1 110.03(10) . . ?
C7 N1 Ni1 109.01(9) . . ?
C8 N1 Ni1 103.88(10) . . ?
C8 N1 C7 109.00(12) . . ?
C9 N1 Ni1 116.82(10) . . ?
C9 N1 C7 109.15(13) . . ?
C9 N1 C8 108.68(13) . . ?
C6 C1 O1 115.81(13) . . ?
C2 C1 O1 121.24(14) . . ?
C2 C1 C6 122.95(14) . . ?
C1 C6 Ni1 123.46(11) . . ?
C1 C6 C5 118.51(14) . . ?
C5 C6 Ni1 117.93(12) . . ?
C6 C5 C7 113.39(14) . . ?
C6 C5 C4 120.37(14) . . ?
C4 C5 C7 126.18(14) . . ?
N1 C7 C5 108.26(12) . . ?
N1 C7 H7A 110.0 . . ?
N1 C7 H7B 110.0 . . ?
C5 C7 H7A 110.0 . . ?
C5 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
C1 C2 H2 121.3 . . ?
C1 C2 C3 117.31(15) . . ?
C3 C2 H2 121.3 . . ?
C5 C4 H4 120.3 . . ?
C3 C4 C5 119.40(14) . . ?
C3 C4 H4 120.3 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.46(15) . . ?
C4 C3 H3 119.3 . . ?
P1 C11 H11 108.3 . . ?
C12 C11 P1 111.57(12) . . ?
C12 C11 H11 108.3 . . ?
C13 C11 P1 108.96(11) . . ?
C13 C11 H11 108.3 . . ?
C13 C11 C12 111.37(15) . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
P1 C14 H14 107.6 . . ?
C16 C14 P1 113.64(12) . . ?
C16 C14 H14 107.6 . . ?
C16 C14 C15 111.26(15) . . ?
C15 C14 P1 109.02(11) . . ?
C15 C14 H14 107.6 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 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 P1 O1 C1 -3.73(11) . . . . ?
Ni1 P1 C11 C12 -78.29(13) . . . . ?
Ni1 P1 C11 C13 45.09(14) . . . . ?
Ni1 P1 C14 C16 -167.98(10) . . . . ?
Ni1 P1 C14 C15 -43.27(14) . . . . ?
Ni1 N1 C7 C5 -30.16(14) . . . . ?
Ni1 C6 C5 C7 -6.77(18) . . . . ?
Ni1 C6 C5 C4 175.78(12) . . . . ?
P1 Ni1 C6 C1 -5.35(13) . . . . ?
P1 Ni1 C6 C5 178.42(13) . . . . ?
P1 O1 C1 C6 0.18(17) . . . . ?
P1 O1 C1 C2 -179.78(12) . . . . ?
O1 P1 C11 C12 162.75(12) . . . . ?
O1 P1 C11 C13 -73.87(12) . . . . ?
O1 P1 C14 C16 -50.33(13) . . . . ?
O1 P1 C14 C15 74.38(13) . . . . ?
O1 C1 C6 Ni1 4.4(2) . . . . ?
O1 C1 C6 C5 -179.43(13) . . . . ?
O1 C1 C2 C3 179.89(14) . . . . ?
N1 Ni1 C6 C1 167.24(14) . . . . ?
N1 Ni1 C6 C5 -8.98(12) . . . . ?
C1 C6 C5 C7 176.81(14) . . . . ?
C1 C6 C5 C4 -0.6(2) . . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
C6 C1 C2 C3 -0.1(2) . . . . ?
C6 C5 C7 N1 24.63(18) . . . . ?
C6 C5 C4 C3 0.3(2) . . . . ?
C5 C4 C3 C2 0.2(2) . . . . ?
C7 C5 C4 C3 -176.79(15) . . . . ?
C2 C1 C6 Ni1 -175.68(12) . . . . ?
C2 C1 C6 C5 0.5(2) . . . . ?
C4 C5 C7 N1 -158.10(15) . . . . ?
C11 P1 O1 C1 124.20(11) . . . . ?
C11 P1 C14 C16 53.88(14) . . . . ?
C11 P1 C14 C15 178.59(13) . . . . ?
C8 N1 C7 C5 82.61(15) . . . . ?
C14 P1 O1 C1 -126.78(11) . . . . ?
C14 P1 C11 C12 57.24(14) . . . . ?
C14 P1 C11 C13 -179.38(12) . . . . ?
C9 N1 C7 C5 -158.83(13) . . . . ?

# end Validation Reply Form
_olex2_exptl_crystal_mounting_method 
'on a glass microfibre covered with parathone oil.'
_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT041_sm176_150k_0m       
;
PROBLEM: Calc. and Reported SumFormula    Strings  Differ     Please Check 
RESPONSE: Methyl (C10) and Br1 fragment are substitutionally disordered.
The fraction of methyl fragment constituted 91% and Br1 9%.  
;
_vrf_PLAT077_sm176_150k_0m       
;
PROBLEM: Unitcell Contains Non-integer Number of Atoms ..     Please Check 
RESPONSE: Methyl (C10) and Br1 fragment are substitutionally disordered.
The fraction of methyl fragment constituted 91% and Br1 9%.  
;
####################################################################### 
# 
# 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_a1
_database_code_depnum_ccdc_archive 'CCDC 2221355'
loop_
_audit_author_name
_audit_author_address
'Konstantin Lyssenko'
;Chemical Department MSU
Russia
;
_audit_update_record             
;
2022-11-22 deposited with the CCDC.	2023-02-07 downloaded from the CCDC.
;
_audit_creation_date             2021-05-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6257)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H30 N Ni O P S'
_chemical_formula_sum            'C21 H30 N Ni O P S'
_chemical_formula_weight         434.20
_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'
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1019(4)
_cell_length_b                   9.5253(4)
_cell_length_c                   13.2196(5)
_cell_angle_alpha                109.0510(10)
_cell_angle_beta                 94.1800(10)
_cell_angle_gamma                102.8170(10)
_cell_volume                     1043.14(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5711
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.55
_cell_measurement_theta_min      2.552
_shelx_estimated_absorpt_T_max   0.850
_shelx_estimated_absorpt_T_min   0.768
_exptl_absorpt_coefficient_mu    1.117
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_correction_T_min  0.5303
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1156 before and 0.0460 after correction.
The Ratio of minimum to maximum transmission is 0.6151.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orangish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.983
_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       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15024
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.555
_diffrn_reflns_theta_min         2.324
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5669
_reflns_number_total             6288
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         6288
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0295
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0377P)²+0.2093P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0797
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C21(H21), C19(H19), C3(H3), C20(H20), C5(H5), C4(H4)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C10(H10A,H10B,H10C), C12(H12A,H12B,
 H12C), C9(H9A,H9B,H9C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
P1 P 0.16297(4) 0.36549(4) 0.17412(3) 0.01355(7) Uani 1 1 d . . . . .
O1 O 0.13453(12) 0.20696(11) 0.20494(8) 0.01791(19) Uani 1 1 d . . . . .
N1 N 0.28678(12) 0.69462(13) 0.47480(9) 0.0141(2) Uani 1 1 d . . . . .
C1 C 0.23198(14) 0.40010(15) 0.37669(10) 0.0137(2) Uani 1 1 d . . . . .
C6 C 0.27195(15) 0.44431(15) 0.48809(11) 0.0150(2) Uani 1 1 d . . . . .
C7 C 0.33876(15) 0.61420(16) 0.54477(11) 0.0163(2) Uani 1 1 d . . . . .
H7A H 0.304113 0.648589 0.615957 0.020 Uiso 1 1 calc R U . . .
H7B H 0.451560 0.638147 0.556988 0.020 Uiso 1 1 calc R U . . .
C17 C 0.54336(16) 0.77023(15) 0.26086(11) 0.0164(2) Uani 1 1 d . . . . .
H17 H 0.528101 0.688208 0.288120 0.020 Uiso 1 1 calc R U . . .
C8 C 0.27436(16) 0.31623(16) 0.06433(11) 0.0186(3) Uani 1 1 d . . . . .
H8 H 0.222339 0.209226 0.014375 0.022 Uiso 1 1 calc R U . . .
C16 C 0.41741(15) 0.81789(14) 0.23051(10) 0.0145(2) Uani 1 1 d . . . . .
C18 C 0.69077(16) 0.84121(17) 0.25173(11) 0.0186(3) Uani 1 1 d . . . . .
H18 H 0.774684 0.807881 0.273534 0.022 Uiso 1 1 calc R U . . .
C21 C 0.44460(16) 0.93999(15) 0.19137(11) 0.0177(2) Uani 1 1 d . . . . .
H21 H 0.361629 0.976236 0.171737 0.021 Uiso 1 1 calc R U . . .
C2 C 0.17548(15) 0.24399(15) 0.31573(11) 0.0153(2) Uani 1 1 d . . . . .
C14 C 0.39413(16) 0.84768(15) 0.50278(11) 0.0185(3) Uani 1 1 d . . . . .
H14A H 0.399303 0.906987 0.579646 0.028 Uiso 1 1 calc R U . . .
H14B H 0.358665 0.902110 0.458504 0.028 Uiso 1 1 calc R U . . .
H14C H 0.495674 0.835525 0.488755 0.028 Uiso 1 1 calc R U . . .
C19 C 0.71571(17) 0.96006(17) 0.21107(11) 0.0201(3) Uani 1 1 d . . . . .
H19 H 0.815920 1.007458 0.203904 0.024 Uiso 1 1 calc R U . . .
C3 C 0.16009(16) 0.13112(16) 0.36154(12) 0.0189(3) Uani 1 1 d . . . . .
H3 H 0.124142 0.025146 0.318270 0.023 Uiso 1 1 calc R U . . .
C20 C 0.59178(17) 1.00878(17) 0.18094(12) 0.0208(3) Uani 1 1 d . . . . .
H20 H 0.607722 1.090004 0.152892 0.025 Uiso 1 1 calc R U . . .
C11 C -0.02661(16) 0.35380(16) 0.11128(11) 0.0186(3) Uani 1 1 d . . . . .
H11 H -0.015154 0.433895 0.076769 0.022 Uiso 1 1 calc R U . . .
C5 C 0.25435(15) 0.33417(17) 0.53745(11) 0.0184(3) Uani 1 1 d . . . . .
H5 H 0.279596 0.364664 0.613865 0.022 Uiso 1 1 calc R U . . .
C4 C 0.19953(16) 0.17910(17) 0.47403(12) 0.0198(3) Uani 1 1 d . . . . .
H4 H 0.188659 0.104239 0.507910 0.024 Uiso 1 1 calc R U . . .
C15 C 0.13417(15) 0.71753(16) 0.49618(12) 0.0189(3) Uani 1 1 d . . . . .
H15A H 0.062894 0.617961 0.484394 0.028 Uiso 1 1 calc R U . . .
H15B H 0.096767 0.764141 0.446931 0.028 Uiso 1 1 calc R U . . .
H15C H 0.142197 0.785591 0.571328 0.028 Uiso 1 1 calc R U . . .
C10 C 0.2819(2) 0.42150(19) -0.00146(13) 0.0261(3) Uani 1 1 d . . . . .
H10A H 0.179211 0.407900 -0.037767 0.039 Uiso 1 1 calc R U . . .
H10B H 0.348533 0.395694 -0.055872 0.039 Uiso 1 1 calc R U . . .
H10C H 0.322675 0.528724 0.046866 0.039 Uiso 1 1 calc R U . . .
C12 C -0.10233(19) 0.19813(19) 0.02257(13) 0.0277(3) Uani 1 1 d . . . . .
H12A H -0.041547 0.181040 -0.036405 0.042 Uiso 1 1 calc R U . . .
H12B H -0.205213 0.197526 -0.005521 0.042 Uiso 1 1 calc R U . . .
H12C H -0.108708 0.116162 0.052843 0.042 Uiso 1 1 calc R U . . .
C9 C 0.43300(18) 0.31542(19) 0.11062(14) 0.0275(3) Uani 1 1 d . . . . .
H9A H 0.491064 0.420938 0.153644 0.041 Uiso 1 1 calc R U . . .
H9B H 0.486537 0.272114 0.051069 0.041 Uiso 1 1 calc R U . . .
H9C H 0.423059 0.252672 0.156802 0.041 Uiso 1 1 calc R U . . .
C13 C -0.12586(17) 0.39426(19) 0.19943(13) 0.0258(3) Uani 1 1 d . . . . .
H13A H -0.131514 0.323224 0.239339 0.039 Uiso 1 1 calc R U . . .
H13B H -0.228708 0.385618 0.165969 0.039 Uiso 1 1 calc R U . . .
H13C H -0.080984 0.499869 0.249480 0.039 Uiso 1 1 calc R U . . .
Ni1 Ni 0.24477(2) 0.55499(2) 0.31805(2) 0.01210(5) Uani 1 1 d . . . . .
S1 S 0.22973(4) 0.72947(4) 0.23934(3) 0.01590(7) 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
P1 O1 1.6604(10) . ?
P1 C8 1.8264(14) . ?
P1 C11 1.8235(14) . ?
P1 Ni1 2.0947(4) . ?
O1 C2 1.3904(16) . ?
N1 C7 1.4920(18) . ?
N1 C14 1.4766(17) . ?
N1 C15 1.4861(17) . ?
N1 Ni1 2.0171(11) . ?
C1 C6 1.3883(18) . ?
C1 C2 1.3939(18) . ?
C1 Ni1 1.8641(13) . ?
C6 C7 1.5017(19) . ?
C6 C5 1.3928(19) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C17 H17 0.9500 . ?
C17 C16 1.4014(18) . ?
C17 C18 1.3951(19) . ?
C8 H8 1.0000 . ?
C8 C10 1.521(2) . ?
C8 C9 1.529(2) . ?
C16 C21 1.4018(18) . ?
C16 S1 1.7596(14) . ?
C18 H18 0.9500 . ?
C18 C19 1.387(2) . ?
C21 H21 0.9500 . ?
C21 C20 1.393(2) . ?
C2 C3 1.3831(19) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C19 H19 0.9500 . ?
C19 C20 1.391(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.398(2) . ?
C20 H20 0.9500 . ?
C11 H11 1.0000 . ?
C11 C12 1.530(2) . ?
C11 C13 1.529(2) . ?
C5 H5 0.9500 . ?
C5 C4 1.392(2) . ?
C4 H4 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
Ni1 S1 2.2524(4) . ?

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 P1 C8 100.31(6) . . ?
O1 P1 C11 102.73(6) . . ?
O1 P1 Ni1 108.07(4) . . ?
C8 P1 Ni1 123.25(5) . . ?
C11 P1 C8 106.52(7) . . ?
C11 P1 Ni1 113.35(5) . . ?
C2 O1 P1 110.39(8) . . ?
C7 N1 Ni1 109.88(8) . . ?
C14 N1 C7 109.24(11) . . ?
C14 N1 C15 107.95(10) . . ?
C14 N1 Ni1 117.23(9) . . ?
C15 N1 C7 109.31(11) . . ?
C15 N1 Ni1 102.87(8) . . ?
C6 C1 C2 118.72(12) . . ?
C6 C1 Ni1 117.68(10) . . ?
C2 C1 Ni1 123.46(10) . . ?
C1 C6 C7 114.15(12) . . ?
C1 C6 C5 120.28(12) . . ?
C5 C6 C7 125.52(12) . . ?
N1 C7 C6 108.03(11) . . ?
N1 C7 H7A 110.1 . . ?
N1 C7 H7B 110.1 . . ?
C6 C7 H7A 110.1 . . ?
C6 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C18 C17 C16 121.11(13) . . ?
P1 C8 H8 107.6 . . ?
C10 C8 P1 112.34(10) . . ?
C10 C8 H8 107.6 . . ?
C10 C8 C9 112.13(13) . . ?
C9 C8 P1 109.43(10) . . ?
C9 C8 H8 107.6 . . ?
C17 C16 C21 117.78(12) . . ?
C17 C16 S1 122.34(10) . . ?
C21 C16 S1 119.88(10) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.49(13) . . ?
C19 C18 H18 119.8 . . ?
C16 C21 H21 119.6 . . ?
C20 C21 C16 120.79(13) . . ?
C20 C21 H21 119.6 . . ?
O1 C2 C1 116.11(12) . . ?
C3 C2 O1 121.27(12) . . ?
C3 C2 C1 122.62(13) . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C18 C19 H19 120.5 . . ?
C18 C19 C20 118.98(13) . . ?
C20 C19 H19 120.5 . . ?
C2 C3 H3 121.3 . . ?
C2 C3 C4 117.39(13) . . ?
C4 C3 H3 121.3 . . ?
C21 C20 H20 119.6 . . ?
C19 C20 C21 120.83(14) . . ?
C19 C20 H20 119.6 . . ?
P1 C11 H11 107.5 . . ?
C12 C11 P1 113.44(11) . . ?
C12 C11 H11 107.5 . . ?
C13 C11 P1 109.09(10) . . ?
C13 C11 H11 107.5 . . ?
C13 C11 C12 111.58(12) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 C6 119.52(13) . . ?
C4 C5 H5 120.2 . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.43(13) . . ?
C5 C4 H4 119.3 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
P1 Ni1 S1 94.310(14) . . ?
N1 Ni1 P1 163.11(3) . . ?
N1 Ni1 S1 99.13(3) . . ?
C1 Ni1 P1 81.89(4) . . ?
C1 Ni1 N1 83.64(5) . . ?
C1 Ni1 S1 173.02(4) . . ?
C16 S1 Ni1 107.03(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
P1 O1 C2 C1 -0.80(14) . . . . ?
P1 O1 C2 C3 179.09(11) . . . . ?
O1 P1 C8 C10 164.44(10) . . . . ?
O1 P1 C8 C9 -70.33(11) . . . . ?
O1 P1 C11 C12 -49.93(12) . . . . ?
O1 P1 C11 C13 75.12(11) . . . . ?
O1 C2 C3 C4 -178.02(12) . . . . ?
C1 C6 C7 N1 22.77(15) . . . . ?
C1 C6 C5 C4 1.4(2) . . . . ?
C1 C2 C3 C4 1.9(2) . . . . ?
C6 C1 C2 O1 178.75(11) . . . . ?
C6 C1 C2 C3 -1.1(2) . . . . ?
C6 C1 Ni1 P1 -178.75(10) . . . . ?
C6 C1 Ni1 N1 -7.49(10) . . . . ?
C6 C5 C4 C3 -0.6(2) . . . . ?
C7 C6 C5 C4 -175.91(13) . . . . ?
C17 C16 C21 C20 1.41(19) . . . . ?
C17 C16 S1 Ni1 4.78(12) . . . . ?
C17 C18 C19 C20 0.9(2) . . . . ?
C8 P1 O1 C2 128.97(9) . . . . ?
C8 P1 C11 C12 55.05(12) . . . . ?
C8 P1 C11 C13 -179.90(10) . . . . ?
C16 C17 C18 C19 -0.7(2) . . . . ?
C16 C21 C20 C19 -1.3(2) . . . . ?
C18 C17 C16 C21 -0.44(19) . . . . ?
C18 C17 C16 S1 179.19(10) . . . . ?
C18 C19 C20 C21 0.1(2) . . . . ?
C21 C16 S1 Ni1 -175.60(9) . . . . ?
C2 C1 C6 C7 177.06(11) . . . . ?
C2 C1 C6 C5 -0.54(19) . . . . ?
C2 C1 Ni1 P1 -3.01(11) . . . . ?
C2 C1 Ni1 N1 168.24(12) . . . . ?
C2 C3 C4 C5 -1.0(2) . . . . ?
C14 N1 C7 C6 -157.20(10) . . . . ?
C11 P1 O1 C2 -121.31(9) . . . . ?
C11 P1 C8 C10 57.73(12) . . . . ?
C11 P1 C8 C9 -177.04(10) . . . . ?
C5 C6 C7 N1 -159.78(12) . . . . ?
C15 N1 C7 C6 84.89(12) . . . . ?
Ni1 P1 O1 C2 -1.23(9) . . . . ?
Ni1 P1 C8 C10 -75.81(12) . . . . ?
Ni1 P1 C8 C9 49.42(12) . . . . ?
Ni1 P1 C11 C12 -166.28(9) . . . . ?
Ni1 P1 C11 C13 -41.23(11) . . . . ?
Ni1 N1 C7 C6 -27.30(12) . . . . ?
Ni1 C1 C6 C7 -7.00(15) . . . . ?
Ni1 C1 C6 C5 175.40(10) . . . . ?
Ni1 C1 C2 O1 3.06(17) . . . . ?
Ni1 C1 C2 C3 -176.84(11) . . . . ?
S1 C16 C21 C20 -178.23(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_sad
_database_code_depnum_ccdc_archive 'CCDC 2221356'
loop_
_audit_author_name
_audit_author_address
'Konstantin Lyssenko'
;Chemical Department MSU
Russia
;
_audit_update_record             
;
2022-11-22 deposited with the CCDC.	2023-02-07 downloaded from the CCDC.
;
_audit_creation_date             2021-05-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6257)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H25 F3 N Ni O4 P S'
_chemical_formula_sum            'C16 H25 F3 N Ni O4 P S'
_chemical_formula_weight         474.11
_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'
F F 0.0171 0.0103 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.8050(2)
_cell_length_b                   9.9384(3)
_cell_length_c                   26.7534(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.5420(10)
_cell_angle_gamma                90
_cell_volume                     2061.73(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6325
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.492
_cell_measurement_theta_min      2.188
_shelx_estimated_absorpt_T_max   0.844
_shelx_estimated_absorpt_T_min   0.759
_exptl_absorpt_coefficient_mu    1.167
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0721 before and 0.0506 after correction.
The Ratio of minimum to maximum transmission is 0.9077.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   0.831
_exptl_transmission_factor_min   0.732
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            22476
_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         30.525
_diffrn_reflns_theta_min         2.188
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5116
_reflns_number_total             6286
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         6286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.024
_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)+(0.0289P)²+0.7074P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0702
_refine_ls_wR_factor_ref         0.0746
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C4(H4)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C13(H13A,H13B,H13C), C10(H10A,H10B,
 H10C), C12(H12A,H12B,H12C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.42116(3) 0.33545(2) 0.39918(2) 0.01283(6) Uani 1 1 d . . . . .
S1 S 0.69619(5) 0.12345(4) 0.38438(2) 0.01531(8) Uani 1 1 d . . . . .
P1 P 0.46138(5) 0.45473(4) 0.33543(2) 0.01428(9) Uani 1 1 d . . . . .
F3 F 0.58804(16) -0.12535(11) 0.38530(5) 0.0338(3) Uani 1 1 d . . . . .
O2 O 0.51275(15) 0.16215(11) 0.37921(5) 0.0182(2) Uani 1 1 d . . . . .
O3 O 0.79660(16) 0.19485(13) 0.35160(5) 0.0244(3) Uani 1 1 d . . . . .
O1 O 0.38099(15) 0.60528(11) 0.34442(4) 0.0182(2) Uani 1 1 d . . . . .
F1 F 0.60399(19) -0.04541(13) 0.31158(4) 0.0434(3) Uani 1 1 d . . . . .
F2 F 0.83486(17) -0.09933(12) 0.35830(5) 0.0429(3) Uani 1 1 d . . . . .
O4 O 0.77008(16) 0.10445(14) 0.43528(5) 0.0243(3) Uani 1 1 d . . . . .
N1 N 0.31697(17) 0.25739(14) 0.45740(5) 0.0164(3) Uani 1 1 d . . . . .
C2 C 0.3130(2) 0.61073(17) 0.39013(6) 0.0165(3) Uani 1 1 d . . . . .
C1 C 0.3272(2) 0.49452(17) 0.41909(6) 0.0152(3) Uani 1 1 d . . . . .
C6 C 0.2637(2) 0.49520(18) 0.46577(6) 0.0180(3) Uani 1 1 d . . . . .
C5 C 0.1871(2) 0.61085(19) 0.48236(7) 0.0231(4) Uani 1 1 d . . . . .
H5 H 0.144109 0.611686 0.514179 0.028 Uiso 1 1 calc R U . . .
C3 C 0.2366(2) 0.72724(17) 0.40564(7) 0.0205(3) Uani 1 1 d . . . . .
H3 H 0.227391 0.805606 0.385178 0.025 Uiso 1 1 calc R U . . .
C11 C 0.6770(2) 0.49488(17) 0.32029(6) 0.0186(3) Uani 1 1 d . . . . .
H11 H 0.729813 0.410047 0.309004 0.022 Uiso 1 1 calc R U . . .
C7 C 0.2932(2) 0.36665(18) 0.49437(6) 0.0201(3) Uani 1 1 d . . . . .
H7A H 0.193120 0.346310 0.512724 0.024 Uiso 1 1 calc R U . . .
H7B H 0.397172 0.374241 0.519127 0.024 Uiso 1 1 calc R U . . .
C4 C 0.1738(2) 0.72502(19) 0.45228(7) 0.0245(4) Uani 1 1 d . . . . .
H4 H 0.120727 0.803395 0.463785 0.029 Uiso 1 1 calc R U . . .
C15 C 0.4057(2) 0.14166(19) 0.48370(7) 0.0246(4) Uani 1 1 d . . . . .
H15A H 0.415733 0.068430 0.459674 0.037 Uiso 1 1 calc R U . . .
H15B H 0.339208 0.110637 0.510426 0.037 Uiso 1 1 calc R U . . .
H15C H 0.521113 0.169209 0.498444 0.037 Uiso 1 1 calc R U . . .
C14 C 0.1450(2) 0.21069(19) 0.43455(7) 0.0218(4) Uani 1 1 d . . . . .
H14A H 0.078567 0.287594 0.419902 0.033 Uiso 1 1 calc R U . . .
H14B H 0.083504 0.169018 0.460511 0.033 Uiso 1 1 calc R U . . .
H14C H 0.159458 0.144637 0.408159 0.033 Uiso 1 1 calc R U . . .
C16 C 0.6789(2) -0.04573(17) 0.35864(7) 0.0232(4) Uani 1 1 d . . . . .
C8 C 0.3313(2) 0.40159(18) 0.27783(6) 0.0228(4) Uani 1 1 d . . . . .
H8 H 0.322971 0.478897 0.253745 0.027 Uiso 1 1 calc R U . . .
C13 C 0.7855(2) 0.54225(19) 0.36835(7) 0.0245(4) Uani 1 1 d . . . . .
H13A H 0.733404 0.623209 0.381099 0.037 Uiso 1 1 calc R U . . .
H13B H 0.902726 0.562808 0.360914 0.037 Uiso 1 1 calc R U . . .
H13C H 0.789695 0.471061 0.393809 0.037 Uiso 1 1 calc R U . . .
C10 C 0.4148(3) 0.2836(2) 0.25315(7) 0.0325(5) Uani 1 1 d . . . . .
H10A H 0.525911 0.312025 0.242955 0.049 Uiso 1 1 calc R U . . .
H10B H 0.338969 0.253895 0.223473 0.049 Uiso 1 1 calc R U . . .
H10C H 0.433025 0.209125 0.277180 0.049 Uiso 1 1 calc R U . . .
C12 C 0.6763(3) 0.59730(19) 0.27792(7) 0.0288(4) Uani 1 1 d . . . . .
H12A H 0.610772 0.561300 0.247414 0.043 Uiso 1 1 calc R U . . .
H12B H 0.795058 0.615600 0.271381 0.043 Uiso 1 1 calc R U . . .
H12C H 0.622453 0.680906 0.287709 0.043 Uiso 1 1 calc R U . . .
C9 C 0.1499(3) 0.3683(2) 0.29004(8) 0.0378(5) Uani 1 1 d . . . . .
H9A H 0.154900 0.291695 0.313240 0.057 Uiso 1 1 calc R U . . .
H9B H 0.076885 0.345218 0.258960 0.057 Uiso 1 1 calc R U . . .
H9C H 0.101352 0.446444 0.305750 0.057 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 P1 2.1295(5) . ?
Ni1 O2 1.9621(11) . ?
Ni1 N1 1.9944(13) . ?
Ni1 C1 1.8465(16) . ?
S1 O2 1.4737(12) . ?
S1 O3 1.4296(13) . ?
S1 O4 1.4295(13) . ?
S1 C16 1.8162(18) . ?
P1 O1 1.6507(12) . ?
P1 C11 1.8198(17) . ?
P1 C8 1.8242(17) . ?
F3 C16 1.324(2) . ?
O1 C2 1.3886(19) . ?
F1 C16 1.326(2) . ?
F2 C16 1.329(2) . ?
N1 C7 1.494(2) . ?
N1 C15 1.479(2) . ?
N1 C14 1.484(2) . ?
C2 C1 1.388(2) . ?
C2 C3 1.388(2) . ?
C1 C6 1.395(2) . ?
C6 C5 1.391(2) . ?
C6 C7 1.494(2) . ?
C5 H5 0.9500 . ?
C5 C4 1.388(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.391(2) . ?
C11 H11 1.0000 . ?
C11 C13 1.531(2) . ?
C11 C12 1.523(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C4 H4 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C8 H8 1.0000 . ?
C8 C10 1.528(3) . ?
C8 C9 1.525(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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
O2 Ni1 P1 100.31(4) . . ?
O2 Ni1 N1 93.72(5) . . ?
N1 Ni1 P1 162.26(4) . . ?
C1 Ni1 P1 81.61(5) . . ?
C1 Ni1 O2 177.49(6) . . ?
C1 Ni1 N1 84.10(6) . . ?
O2 S1 C16 100.19(8) . . ?
O3 S1 O2 114.05(7) . . ?
O3 S1 O4 117.39(8) . . ?
O3 S1 C16 104.42(8) . . ?
O4 S1 O2 113.96(7) . . ?
O4 S1 C16 104.09(8) . . ?
O1 P1 Ni1 107.14(4) . . ?
O1 P1 C11 102.14(7) . . ?
O1 P1 C8 101.61(7) . . ?
C11 P1 Ni1 121.66(6) . . ?
C11 P1 C8 108.38(8) . . ?
C8 P1 Ni1 113.38(6) . . ?
S1 O2 Ni1 125.72(7) . . ?
C2 O1 P1 110.70(10) . . ?
C7 N1 Ni1 109.06(10) . . ?
C15 N1 Ni1 117.62(10) . . ?
C15 N1 C7 109.68(13) . . ?
C15 N1 C14 107.78(14) . . ?
C14 N1 Ni1 103.30(10) . . ?
C14 N1 C7 108.98(13) . . ?
C1 C2 O1 116.41(14) . . ?
C3 C2 O1 121.09(15) . . ?
C3 C2 C1 122.50(15) . . ?
C2 C1 Ni1 124.10(12) . . ?
C2 C1 C6 118.79(15) . . ?
C6 C1 Ni1 117.10(13) . . ?
C1 C6 C7 113.87(15) . . ?
C5 C6 C1 119.93(16) . . ?
C5 C6 C7 126.16(15) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 C6 119.78(16) . . ?
C4 C5 H5 120.1 . . ?
C2 C3 H3 121.2 . . ?
C2 C3 C4 117.52(16) . . ?
C4 C3 H3 121.2 . . ?
P1 C11 H11 107.8 . . ?
C13 C11 P1 108.50(12) . . ?
C13 C11 H11 107.8 . . ?
C12 C11 P1 112.76(13) . . ?
C12 C11 H11 107.8 . . ?
C12 C11 C13 111.99(15) . . ?
N1 C7 H7A 110.1 . . ?
N1 C7 H7B 110.1 . . ?
C6 C7 N1 107.82(13) . . ?
C6 C7 H7A 110.1 . . ?
C6 C7 H7B 110.1 . . ?
H7A C7 H7B 108.5 . . ?
C5 C4 C3 121.48(16) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
F3 C16 S1 111.71(12) . . ?
F3 C16 F1 107.89(15) . . ?
F3 C16 F2 108.13(15) . . ?
F1 C16 S1 111.31(12) . . ?
F1 C16 F2 107.44(15) . . ?
F2 C16 S1 110.19(13) . . ?
P1 C8 H8 108.1 . . ?
C10 C8 P1 111.32(13) . . ?
C10 C8 H8 108.1 . . ?
C9 C8 P1 108.83(13) . . ?
C9 C8 H8 108.1 . . ?
C9 C8 C10 112.20(17) . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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 P1 O1 C2 0.42(11) . . . . ?
Ni1 P1 C11 C13 -47.03(14) . . . . ?
Ni1 P1 C11 C12 -171.68(10) . . . . ?
Ni1 P1 C8 C10 -82.17(14) . . . . ?
Ni1 P1 C8 C9 41.99(15) . . . . ?
Ni1 N1 C7 C6 29.92(15) . . . . ?
Ni1 C1 C6 C5 -178.29(13) . . . . ?
Ni1 C1 C6 C7 3.94(19) . . . . ?
P1 Ni1 C1 C2 2.24(13) . . . . ?
P1 Ni1 C1 C6 -179.25(13) . . . . ?
P1 O1 C2 C1 1.10(18) . . . . ?
P1 O1 C2 C3 -179.38(13) . . . . ?
O2 S1 C16 F3 -61.71(14) . . . . ?
O2 S1 C16 F1 58.97(14) . . . . ?
O2 S1 C16 F2 178.06(13) . . . . ?
O3 S1 O2 Ni1 -69.11(11) . . . . ?
O3 S1 C16 F3 -179.99(13) . . . . ?
O3 S1 C16 F1 -59.31(15) . . . . ?
O3 S1 C16 F2 59.78(14) . . . . ?
O1 P1 C11 C13 72.10(13) . . . . ?
O1 P1 C11 C12 -52.56(14) . . . . ?
O1 P1 C8 C10 163.21(13) . . . . ?
O1 P1 C8 C9 -72.63(14) . . . . ?
O1 C2 C1 Ni1 -2.6(2) . . . . ?
O1 C2 C1 C6 178.90(14) . . . . ?
O1 C2 C3 C4 -179.08(15) . . . . ?
O4 S1 O2 Ni1 69.45(11) . . . . ?
O4 S1 C16 F3 56.35(15) . . . . ?
O4 S1 C16 F1 177.03(13) . . . . ?
O4 S1 C16 F2 -63.88(14) . . . . ?
N1 Ni1 C1 C2 -167.23(15) . . . . ?
N1 Ni1 C1 C6 11.28(12) . . . . ?
C2 C1 C6 C5 0.3(2) . . . . ?
C2 C1 C6 C7 -177.46(15) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C1 C6 C5 C4 0.2(3) . . . . ?
C1 C6 C7 N1 -22.68(19) . . . . ?
C6 C5 C4 C3 -0.4(3) . . . . ?
C5 C6 C7 N1 159.71(16) . . . . ?
C3 C2 C1 Ni1 177.87(13) . . . . ?
C3 C2 C1 C6 -0.6(2) . . . . ?
C11 P1 O1 C2 -128.49(11) . . . . ?
C11 P1 C8 C10 56.08(16) . . . . ?
C11 P1 C8 C9 -179.75(13) . . . . ?
C7 C6 C5 C4 177.66(17) . . . . ?
C15 N1 C7 C6 160.04(13) . . . . ?
C14 N1 C7 C6 -82.18(16) . . . . ?
C16 S1 O2 Ni1 179.96(9) . . . . ?
C8 P1 O1 C2 119.59(11) . . . . ?
C8 P1 C11 C13 178.86(12) . . . . ?
C8 P1 C11 C12 54.20(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 2221357'
loop_
_audit_author_name
_audit_author_address
'Konstantin Lyssenko'
;Chemical Department MSU
Russia
;
_audit_update_record             
;
2022-11-22 deposited with the CCDC.	2023-02-07 downloaded from the CCDC.
;
_audit_creation_date             2021-05-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6257)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H25 N2 Ni O4 P'
_chemical_formula_sum            'C15 H25 N2 Ni O4 P'
_chemical_formula_weight         387.05
_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'
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.2003(9)
_cell_length_b                   9.4423(8)
_cell_length_c                   16.3874(13)
_cell_angle_alpha                90
_cell_angle_beta                 101.156(3)
_cell_angle_gamma                90
_cell_volume                     1700.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    458
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3
_shelx_estimated_absorpt_T_max   0.824
_shelx_estimated_absorpt_T_min   0.736
_exptl_absorpt_coefficient_mu    1.256
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orangish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1098
_diffrn_reflns_av_unetI/netI     0.0995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17214
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.997
_diffrn_reflns_theta_min         2.439
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  "Bruker APEX II CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3413
_reflns_number_total             4953
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_refine_diff_density_max         0.594
_refine_diff_density_min         -0.442
_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     214
_refine_ls_number_reflns         4953
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0613
_refine_ls_restrained_S_all      1.054
_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)+(0.0267P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1084
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C4(H4)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C9(H9A,H9B,H9C), C12(H12A,H12B,H12C), C15(H15A,H15B,
 H15C), C10(H10A,H10B,H10C), C13(H13A,H13B,H13C)
;
_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 0.53861(3) 0.63568(4) 0.22962(2) 0.01282(10) Uani 1 1 d . . . . .
P1 P 0.47660(7) 0.62471(8) 0.34417(4) 0.01384(16) Uani 1 1 d . . . . .
O1 O 0.59678(18) 0.5889(2) 0.41756(12) 0.0167(5) Uani 1 1 d . . . . .
O2 O 0.38535(19) 0.6873(2) 0.15784(13) 0.0212(5) Uani 1 1 d . . . . .
O3 O 0.3549(2) 0.4686(3) 0.11767(14) 0.0261(5) Uani 1 1 d . . . . .
O4 O 0.2316(2) 0.6335(3) 0.06122(14) 0.0317(6) Uani 1 1 d . . . . .
N1 N 0.6375(2) 0.6242(3) 0.13999(14) 0.0148(5) Uani 1 1 d . . . . .
N2 N 0.3225(2) 0.5946(3) 0.11115(16) 0.0218(6) Uani 1 1 d . . . . .
C1 C 0.6880(3) 0.6197(3) 0.30043(17) 0.0141(6) Uani 1 1 d . . . . .
C2 C 0.7031(3) 0.5986(3) 0.38592(18) 0.0149(6) Uani 1 1 d . . . . .
C6 C 0.7913(2) 0.6355(3) 0.26587(18) 0.0158(6) Uani 1 1 d . . . . .
C5 C 0.9067(3) 0.6227(3) 0.31526(19) 0.0173(6) Uani 1 1 d . . . . .
H5 H 0.977117 0.629282 0.291158 0.021 Uiso 1 1 calc R U . . .
C8 C 0.3749(3) 0.4801(3) 0.35828(18) 0.0154(6) Uani 1 1 d . . . . .
H8 H 0.380789 0.464846 0.419316 0.018 Uiso 1 1 calc R U . . .
C14 C 0.6457(3) 0.4711(3) 0.11884(19) 0.0185(6) Uani 1 1 d . . . . .
H14A H 0.689784 0.419869 0.167425 0.028 Uiso 1 1 calc R U . . .
H14B H 0.689026 0.461266 0.072628 0.028 Uiso 1 1 calc R U . . .
H14C H 0.563511 0.431838 0.102565 0.028 Uiso 1 1 calc R U . . .
C3 C 0.8164(3) 0.5905(3) 0.43690(18) 0.0179(6) Uani 1 1 d . . . . .
H3 H 0.824748 0.578680 0.495300 0.022 Uiso 1 1 calc R U . . .
C4 C 0.9179(3) 0.6003(3) 0.39992(19) 0.0183(7) Uani 1 1 d . . . . .
H4 H 0.996770 0.591357 0.433537 0.022 Uiso 1 1 calc R U . . .
C7 C 0.7632(3) 0.6753(3) 0.17547(17) 0.0156(6) Uani 1 1 d . . . . .
H7A H 0.767882 0.779375 0.169251 0.019 Uiso 1 1 calc R U . . .
H7B H 0.822720 0.630876 0.145876 0.019 Uiso 1 1 calc R U . . .
C9 C 0.4176(3) 0.3450(3) 0.32108(19) 0.0206(7) Uani 1 1 d . . . . .
H9A H 0.403104 0.353455 0.260356 0.031 Uiso 1 1 calc R U . . .
H9B H 0.372317 0.263657 0.336494 0.031 Uiso 1 1 calc R U . . .
H9C H 0.504752 0.331306 0.342558 0.031 Uiso 1 1 calc R U . . .
C11 C 0.4169(3) 0.7859(3) 0.38151(18) 0.0171(6) Uani 1 1 d . . . . .
H11 H 0.336077 0.805347 0.345150 0.021 Uiso 1 1 calc R U . . .
C12 C 0.3972(3) 0.7734(4) 0.47104(18) 0.0225(7) Uani 1 1 d . . . . .
H12A H 0.345391 0.691296 0.475696 0.034 Uiso 1 1 calc R U . . .
H12B H 0.357613 0.859499 0.486068 0.034 Uiso 1 1 calc R U . . .
H12C H 0.475901 0.761375 0.508688 0.034 Uiso 1 1 calc R U . . .
C15 C 0.5879(3) 0.7035(3) 0.06350(18) 0.0198(7) Uani 1 1 d . . . . .
H15A H 0.506367 0.668039 0.039708 0.030 Uiso 1 1 calc R U . . .
H15B H 0.641251 0.691052 0.023189 0.030 Uiso 1 1 calc R U . . .
H15C H 0.583061 0.804340 0.076759 0.030 Uiso 1 1 calc R U . . .
C10 C 0.2421(3) 0.5144(4) 0.31979(19) 0.0210(7) Uani 1 1 d . . . . .
H10A H 0.215126 0.596107 0.348408 0.031 Uiso 1 1 calc R U . . .
H10B H 0.190730 0.432471 0.325705 0.031 Uiso 1 1 calc R U . . .
H10C H 0.235464 0.536646 0.260671 0.031 Uiso 1 1 calc R U . . .
C13 C 0.5005(3) 0.9105(3) 0.3727(2) 0.0222(7) Uani 1 1 d . . . . .
H13A H 0.579301 0.896698 0.409988 0.033 Uiso 1 1 calc R U . . .
H13B H 0.463392 0.998516 0.387311 0.033 Uiso 1 1 calc R U . . .
H13C H 0.512498 0.916055 0.315097 0.033 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 P1 2.1264(9) . ?
Ni1 O2 1.946(2) . ?
Ni1 N1 2.006(3) . ?
Ni1 C1 1.849(3) . ?
P1 O1 1.657(2) . ?
P1 C8 1.821(3) . ?
P1 C11 1.815(3) . ?
O1 C2 1.391(4) . ?
O2 N2 1.280(3) . ?
O3 N2 1.243(4) . ?
O4 N2 1.232(3) . ?
N1 C14 1.493(4) . ?
N1 C7 1.496(3) . ?
N1 C15 1.474(4) . ?
C1 C2 1.393(4) . ?
C1 C6 1.391(4) . ?
C2 C3 1.379(4) . ?
C6 C5 1.391(4) . ?
C6 C7 1.502(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.385(4) . ?
C8 H8 1.0000 . ?
C8 C9 1.530(4) . ?
C8 C10 1.534(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C3 H3 0.9500 . ?
C3 C4 1.391(4) . ?
C4 H4 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 H11 1.0000 . ?
C11 C12 1.530(4) . ?
C11 C13 1.527(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
O2 Ni1 P1 98.36(7) . . ?
O2 Ni1 N1 96.80(9) . . ?
N1 Ni1 P1 164.69(7) . . ?
C1 Ni1 P1 81.52(10) . . ?
C1 Ni1 O2 170.17(12) . . ?
C1 Ni1 N1 83.92(11) . . ?
O1 P1 Ni1 107.01(8) . . ?
O1 P1 C8 101.25(12) . . ?
O1 P1 C11 103.12(12) . . ?
C8 P1 Ni1 117.89(10) . . ?
C11 P1 Ni1 117.46(11) . . ?
C11 P1 C8 107.79(15) . . ?
C2 O1 P1 110.47(17) . . ?
N2 O2 Ni1 120.6(2) . . ?
C14 N1 Ni1 106.84(19) . . ?
C14 N1 C7 107.9(2) . . ?
C7 N1 Ni1 108.04(17) . . ?
C15 N1 Ni1 115.10(19) . . ?
C15 N1 C14 108.9(2) . . ?
C15 N1 C7 109.7(2) . . ?
O3 N2 O2 119.1(2) . . ?
O4 N2 O2 118.7(3) . . ?
O4 N2 O3 122.2(3) . . ?
C2 C1 Ni1 124.2(2) . . ?
C6 C1 Ni1 117.3(2) . . ?
C6 C1 C2 118.5(3) . . ?
O1 C2 C1 116.0(2) . . ?
C3 C2 O1 121.6(3) . . ?
C3 C2 C1 122.4(3) . . ?
C1 C6 C7 113.4(2) . . ?
C5 C6 C1 120.4(3) . . ?
C5 C6 C7 126.1(3) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 C6 119.4(3) . . ?
C4 C5 H5 120.3 . . ?
P1 C8 H8 108.2 . . ?
C9 C8 P1 108.8(2) . . ?
C9 C8 H8 108.2 . . ?
C9 C8 C10 111.4(2) . . ?
C10 C8 P1 111.7(2) . . ?
C10 C8 H8 108.2 . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 C3 H3 121.1 . . ?
C2 C3 C4 117.8(3) . . ?
C4 C3 H3 121.1 . . ?
C5 C4 C3 121.5(3) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
N1 C7 C6 107.7(2) . . ?
N1 C7 H7A 110.2 . . ?
N1 C7 H7B 110.2 . . ?
C6 C7 H7A 110.2 . . ?
C6 C7 H7B 110.2 . . ?
H7A C7 H7B 108.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
P1 C11 H11 107.7 . . ?
C12 C11 P1 112.9(2) . . ?
C12 C11 H11 107.7 . . ?
C13 C11 P1 110.0(2) . . ?
C13 C11 H11 107.7 . . ?
C13 C11 C12 110.8(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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 P1 O1 C2 9.3(2) . . . . ?
Ni1 P1 C8 C9 39.8(2) . . . . ?
Ni1 P1 C8 C10 -83.7(2) . . . . ?
Ni1 P1 C11 C12 -169.36(17) . . . . ?
Ni1 P1 C11 C13 -45.0(2) . . . . ?
Ni1 O2 N2 O3 6.4(4) . . . . ?
Ni1 O2 N2 O4 -173.6(2) . . . . ?
Ni1 N1 C7 C6 32.6(3) . . . . ?
Ni1 C1 C2 O1 0.3(4) . . . . ?
Ni1 C1 C2 C3 -178.5(2) . . . . ?
Ni1 C1 C6 C5 -179.0(2) . . . . ?
Ni1 C1 C6 C7 4.6(4) . . . . ?
P1 Ni1 C1 C2 4.6(2) . . . . ?
P1 Ni1 C1 C6 -172.7(2) . . . . ?
P1 O1 C2 C1 -6.8(3) . . . . ?
P1 O1 C2 C3 172.0(2) . . . . ?
O1 P1 C8 C9 -76.5(2) . . . . ?
O1 P1 C8 C10 160.0(2) . . . . ?
O1 P1 C11 C12 -52.0(2) . . . . ?
O1 P1 C11 C13 72.3(2) . . . . ?
O1 C2 C3 C4 179.6(3) . . . . ?
N1 Ni1 C1 C2 -170.6(3) . . . . ?
N1 Ni1 C1 C6 12.1(2) . . . . ?
C1 C2 C3 C4 -1.7(5) . . . . ?
C1 C6 C5 C4 -2.9(5) . . . . ?
C1 C6 C7 N1 -25.1(4) . . . . ?
C2 C1 C6 C5 3.5(5) . . . . ?
C2 C1 C6 C7 -172.9(3) . . . . ?
C2 C3 C4 C5 2.4(5) . . . . ?
C6 C1 C2 O1 177.6(3) . . . . ?
C6 C1 C2 C3 -1.2(5) . . . . ?
C6 C5 C4 C3 -0.1(5) . . . . ?
C5 C6 C7 N1 158.8(3) . . . . ?
C8 P1 O1 C2 133.3(2) . . . . ?
C8 P1 C11 C12 54.6(2) . . . . ?
C8 P1 C11 C13 178.87(19) . . . . ?
C14 N1 C7 C6 -82.6(3) . . . . ?
C7 C6 C5 C4 173.0(3) . . . . ?
C11 P1 O1 C2 -115.2(2) . . . . ?
C11 P1 C8 C9 175.64(18) . . . . ?
C11 P1 C8 C10 52.2(2) . . . . ?
C15 N1 C7 C6 158.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 2221358'
loop_
_audit_author_name
_audit_author_address
'Konstantin Lyssenko'
;Chemical Department MSU
Russia
;
_audit_update_record             
;
2022-11-22 deposited with the CCDC.	2023-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H33 Br N Ni O P'
_chemical_formula_sum            'C19 H33 Br N Ni O P'
_chemical_formula_weight         461.05

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.8863(7)
_cell_length_b                   14.2089(7)
_cell_length_c                   19.6520(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4156.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3789
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      30.2

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_F_000             1920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    2.939
_shelx_estimated_absorpt_T_min   0.504
_shelx_estimated_absorpt_T_max   0.667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.818
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_source                   'micro-focused sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_reflns_number            27710
_diffrn_reflns_av_unetI/netI     0.0703
_diffrn_reflns_av_R_equivalents  0.0836
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.073
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6004
_reflns_number_gt                4324
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0374P)²+0.7661P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6004
_refine_ls_number_parameters     225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.0993
_refine_ls_wR_factor_gt          0.0884
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001

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 0.66184(2) 0.41225(2) 0.31706(2) 0.02574(9) Uani 1 1 d . . . . .
Ni1 Ni 0.54677(2) 0.30202(3) 0.33841(2) 0.01585(10) Uani 1 1 d . . . . .
P1 P 0.60771(5) 0.26113(5) 0.43035(4) 0.01657(16) Uani 1 1 d . . . . .
O1 O 0.55095(12) 0.17052(15) 0.46151(10) 0.0200(4) Uani 1 1 d . . . . .
N1 N 0.46191(14) 0.32322(17) 0.25660(11) 0.0165(5) Uani 1 1 d . . . . .
C2 C 0.48130(18) 0.1467(2) 0.41726(14) 0.0183(6) Uani 1 1 d . . . . .
C1 C 0.47278(18) 0.2014(2) 0.35940(15) 0.0203(6) Uani 1 1 d . . . . .
C6 C 0.40653(18) 0.1778(2) 0.31206(15) 0.0209(6) Uani 1 1 d . . . . .
C7 C 0.40548(19) 0.2354(2) 0.24811(15) 0.0241(7) Uani 1 1 d . . . . .
H7A H 0.342900 0.253392 0.237053 0.029 Uiso 1 1 calc R U . . .
H7B H 0.429263 0.197482 0.209895 0.029 Uiso 1 1 calc R U . . .
C11 C 0.60364(19) 0.3390(2) 0.50410(14) 0.0214(6) Uani 1 1 d . . . . .
H11 H 0.622523 0.301143 0.544543 0.026 Uiso 1 1 calc R U . . .
C8 C 0.72099(19) 0.2138(2) 0.42669(16) 0.0250(7) Uani 1 1 d . . . . .
H8 H 0.762188 0.265477 0.411966 0.030 Uiso 1 1 calc R U . . .
C17 C 0.5154(2) 0.3409(2) 0.19241(14) 0.0234(7) Uani 1 1 d . . . . .
H17 H 0.549557 0.400631 0.199613 0.028 Uiso 1 1 calc R U . . .
C3 C 0.42540(19) 0.0718(2) 0.43170(16) 0.0245(7) Uani 1 1 d . . . . .
H3 H 0.431427 0.036708 0.472606 0.029 Uiso 1 1 calc R U . . .
C13 C 0.5071(2) 0.3704(2) 0.51649(17) 0.0295(7) Uani 1 1 d . . . . .
H13A H 0.486702 0.409042 0.478172 0.044 Uiso 1 1 calc R U . . .
H13B H 0.504191 0.407436 0.558512 0.044 Uiso 1 1 calc R U . . .
H13C H 0.468336 0.314986 0.520754 0.044 Uiso 1 1 calc R U . . .
C5 C 0.3497(2) 0.1023(2) 0.32433(16) 0.0286(8) Uani 1 1 d . . . . .
H5 H 0.304104 0.086522 0.292465 0.034 Uiso 1 1 calc R U . . .
C18 C 0.4579(2) 0.3549(3) 0.12900(15) 0.0309(8) Uani 1 1 d . . . . .
H18A H 0.420306 0.299125 0.121796 0.046 Uiso 1 1 calc R U . . .
H18B H 0.496983 0.364151 0.089432 0.046 Uiso 1 1 calc R U . . .
H18C H 0.419518 0.410260 0.135004 0.046 Uiso 1 1 calc R U . . .
C4 C 0.3599(2) 0.0498(2) 0.38382(17) 0.0296(7) Uani 1 1 d . . . . .
H4 H 0.321156 -0.002163 0.391813 0.036 Uiso 1 1 calc R U . . .
C19 C 0.5845(2) 0.2632(2) 0.18159(16) 0.0297(7) Uani 1 1 d . . . . .
H19A H 0.613110 0.247817 0.225094 0.045 Uiso 1 1 calc R U . . .
H19B H 0.630203 0.284733 0.149257 0.045 Uiso 1 1 calc R U . . .
H19C H 0.554602 0.207101 0.163445 0.045 Uiso 1 1 calc R U . . .
C12 C 0.6674(2) 0.4229(2) 0.49918(18) 0.0335(8) Uani 1 1 d . . . . .
H12A H 0.729280 0.400229 0.494845 0.050 Uiso 1 1 calc R U . . .
H12B H 0.661929 0.461492 0.540305 0.050 Uiso 1 1 calc R U . . .
H12C H 0.651812 0.460828 0.459234 0.050 Uiso 1 1 calc R U . . .
C14 C 0.3974(2) 0.4045(2) 0.27005(16) 0.0258(7) Uani 1 1 d . . . . .
H14 H 0.351970 0.404292 0.232572 0.031 Uiso 1 1 calc R U . . .
C9 C 0.7246(2) 0.1365(3) 0.37307(19) 0.0390(9) Uani 1 1 d . . . . .
H9A H 0.685538 0.084297 0.386862 0.058 Uiso 1 1 calc R U . . .
H9B H 0.786442 0.113746 0.368535 0.058 Uiso 1 1 calc R U . . .
H9C H 0.704037 0.161598 0.329318 0.058 Uiso 1 1 calc R U . . .
C10 C 0.7535(2) 0.1778(3) 0.49591(19) 0.0383(9) Uani 1 1 d . . . . .
H10A H 0.760896 0.231039 0.527106 0.057 Uiso 1 1 calc R U . . .
H10B H 0.811247 0.145534 0.490299 0.057 Uiso 1 1 calc R U . . .
H10C H 0.709263 0.133774 0.514613 0.057 Uiso 1 1 calc R U . . .
C16 C 0.4422(2) 0.4998(2) 0.26946(19) 0.0375(9) Uani 1 1 d . . . . .
H16A H 0.490608 0.500898 0.303230 0.056 Uiso 1 1 calc R U . . .
H16B H 0.397845 0.548444 0.280601 0.056 Uiso 1 1 calc R U . . .
H16C H 0.467140 0.512065 0.224171 0.056 Uiso 1 1 calc R U . . .
C15 C 0.3468(2) 0.3899(3) 0.33640(17) 0.0348(8) Uani 1 1 d . . . . .
H15A H 0.317286 0.328228 0.335753 0.052 Uiso 1 1 calc R U . . .
H15B H 0.301416 0.439327 0.341616 0.052 Uiso 1 1 calc R U . . .
H15C H 0.389032 0.392647 0.374592 0.052 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Ni1 2.3588(5) . ?
Ni1 C1 1.852(3) . ?
Ni1 N1 2.067(2) . ?
Ni1 P1 2.1037(8) . ?
P1 O1 1.657(2) . ?
P1 C8 1.817(3) . ?
P1 C11 1.825(3) . ?
O1 C2 1.395(3) . ?
N1 C17 1.512(4) . ?
N1 C7 1.513(4) . ?
N1 C14 1.525(4) . ?
C2 C3 1.380(4) . ?
C2 C1 1.383(4) . ?
C1 C6 1.396(4) . ?
C6 C5 1.387(4) . ?
C6 C7 1.500(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C11 C13 1.524(4) . ?
C11 C12 1.527(4) . ?
C11 H11 1.0000 . ?
C8 C9 1.523(5) . ?
C8 C10 1.532(4) . ?
C8 H8 1.0000 . ?
C17 C19 1.524(5) . ?
C17 C18 1.524(4) . ?
C17 H17 1.0000 . ?
C3 C4 1.391(4) . ?
C3 H3 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C5 C4 1.395(5) . ?
C5 H5 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C4 H4 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 C16 1.510(5) . ?
C14 C15 1.520(4) . ?
C14 H14 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
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
C1 Ni1 N1 85.54(11) . . ?
C1 Ni1 P1 81.48(10) . . ?
N1 Ni1 P1 166.42(7) . . ?
C1 Ni1 Br1 169.89(9) . . ?
N1 Ni1 Br1 102.05(7) . . ?
P1 Ni1 Br1 91.32(2) . . ?
O1 P1 C8 101.53(13) . . ?
O1 P1 C11 99.24(12) . . ?
C8 P1 C11 106.68(14) . . ?
O1 P1 Ni1 108.19(8) . . ?
C8 P1 Ni1 117.94(11) . . ?
C11 P1 Ni1 120.03(10) . . ?
C2 O1 P1 109.71(18) . . ?
C17 N1 C7 109.7(2) . . ?
C17 N1 C14 110.5(2) . . ?
C7 N1 C14 107.1(2) . . ?
C17 N1 Ni1 110.58(16) . . ?
C7 N1 Ni1 107.76(17) . . ?
C14 N1 Ni1 111.12(17) . . ?
C3 C2 C1 123.2(3) . . ?
C3 C2 O1 120.5(3) . . ?
C1 C2 O1 116.4(2) . . ?
C2 C1 C6 118.5(3) . . ?
C2 C1 Ni1 124.2(2) . . ?
C6 C1 Ni1 117.2(2) . . ?
C5 C6 C1 120.0(3) . . ?
C5 C6 C7 124.1(3) . . ?
C1 C6 C7 115.8(3) . . ?
C6 C7 N1 110.6(2) . . ?
C6 C7 H7A 109.5 . . ?
N1 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C13 C11 C12 111.6(3) . . ?
C13 C11 P1 109.6(2) . . ?
C12 C11 P1 113.7(2) . . ?
C13 C11 H11 107.2 . . ?
C12 C11 H11 107.2 . . ?
P1 C11 H11 107.2 . . ?
C9 C8 C10 111.3(3) . . ?
C9 C8 P1 109.1(2) . . ?
C10 C8 P1 112.5(2) . . ?
C9 C8 H8 108.0 . . ?
C10 C8 H8 108.0 . . ?
P1 C8 H8 108.0 . . ?
N1 C17 C19 110.6(3) . . ?
N1 C17 C18 114.1(2) . . ?
C19 C17 C18 111.0(3) . . ?
N1 C17 H17 106.9 . . ?
C19 C17 H17 106.9 . . ?
C18 C17 H17 106.9 . . ?
C2 C3 C4 117.2(3) . . ?
C2 C3 H3 121.4 . . ?
C4 C3 H3 121.4 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 C5 C4 119.5(3) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C3 C4 C5 121.6(3) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C16 C14 C15 110.4(3) . . ?
C16 C14 N1 113.6(2) . . ?
C15 C14 N1 110.9(3) . . ?
C16 C14 H14 107.2 . . ?
C15 C14 H14 107.2 . . ?
N1 C14 H14 107.2 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
C8 P1 O1 C2 -123.4(2) . . . . ?
C11 P1 O1 C2 127.34(19) . . . . ?
Ni1 P1 O1 C2 1.39(19) . . . . ?
P1 O1 C2 C3 178.8(2) . . . . ?
P1 O1 C2 C1 -0.9(3) . . . . ?
C3 C2 C1 C6 -2.3(5) . . . . ?
O1 C2 C1 C6 177.3(2) . . . . ?
C3 C2 C1 Ni1 -179.8(2) . . . . ?
O1 C2 C1 Ni1 -0.2(4) . . . . ?
N1 Ni1 C1 C2 -175.1(3) . . . . ?
P1 Ni1 C1 C2 0.9(2) . . . . ?
Br1 Ni1 C1 C2 45.8(7) . . . . ?
N1 Ni1 C1 C6 7.4(2) . . . . ?
P1 Ni1 C1 C6 -176.6(2) . . . . ?
Br1 Ni1 C1 C6 -131.7(5) . . . . ?
C2 C1 C6 C5 1.5(5) . . . . ?
Ni1 C1 C6 C5 179.2(2) . . . . ?
C2 C1 C6 C7 -175.6(3) . . . . ?
Ni1 C1 C6 C7 2.1(4) . . . . ?
C5 C6 C7 N1 168.6(3) . . . . ?
C1 C6 C7 N1 -14.5(4) . . . . ?
C17 N1 C7 C6 139.0(2) . . . . ?
C14 N1 C7 C6 -101.0(3) . . . . ?
Ni1 N1 C7 C6 18.6(3) . . . . ?
O1 P1 C11 C13 -66.8(2) . . . . ?
C8 P1 C11 C13 -171.9(2) . . . . ?
Ni1 P1 C11 C13 50.5(2) . . . . ?
O1 P1 C11 C12 167.5(2) . . . . ?
C8 P1 C11 C12 62.5(3) . . . . ?
Ni1 P1 C11 C12 -75.1(2) . . . . ?
O1 P1 C8 C9 67.7(2) . . . . ?
C11 P1 C8 C9 171.1(2) . . . . ?
Ni1 P1 C8 C9 -50.3(3) . . . . ?
O1 P1 C8 C10 -56.3(3) . . . . ?
C11 P1 C8 C10 47.1(3) . . . . ?
Ni1 P1 C8 C10 -174.2(2) . . . . ?
C7 N1 C17 C19 -66.2(3) . . . . ?
C14 N1 C17 C19 176.0(2) . . . . ?
Ni1 N1 C17 C19 52.5(3) . . . . ?
C7 N1 C17 C18 59.8(3) . . . . ?
C14 N1 C17 C18 -58.0(3) . . . . ?
Ni1 N1 C17 C18 178.5(2) . . . . ?
C1 C2 C3 C4 2.2(5) . . . . ?
O1 C2 C3 C4 -177.4(3) . . . . ?
C1 C6 C5 C4 -0.7(5) . . . . ?
C7 C6 C5 C4 176.1(3) . . . . ?
C2 C3 C4 C5 -1.3(5) . . . . ?
C6 C5 C4 C3 0.6(5) . . . . ?
C17 N1 C14 C16 -52.1(3) . . . . ?
C7 N1 C14 C16 -171.5(3) . . . . ?
Ni1 N1 C14 C16 71.1(3) . . . . ?
C17 N1 C14 C15 -177.1(3) . . . . ?
C7 N1 C14 C15 63.5(3) . . . . ?
Ni1 N1 C14 C15 -53.9(3) . . . . ?

_refine_diff_density_max         0.828
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.114

