# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_rajib651
_database_code_depnum_ccdc_archive 'CCDC 2287044'
loop_
_audit_author_name
_audit_author_address
'Rajib Kumar Sarker'
;University of Montreal
Canada
;
_audit_update_record             
;
2023-08-06 deposited with the CCDC.	2024-05-24 downloaded from the CCDC.
;
_audit_creation_date             2023-08-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '4(C21 H37 Br N Ni O2 P)'
_chemical_formula_sum            'C84 H148 Br4 N4 Ni4 O8 P4'
_chemical_formula_weight         2020.42
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 -0.9338 1.0006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -1.3357 3.2904 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2543 0.3332 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   15.1559(3)
_cell_length_b                   11.6422(3)
_cell_length_c                   15.0239(3)
_cell_angle_alpha                90
_cell_angle_beta                 117.4860(10)
_cell_angle_gamma                90
_cell_volume                     2351.71(9)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9832
_cell_measurement_temperature    150
_cell_measurement_theta_max      56.983
_cell_measurement_theta_min      2.885
_shelx_estimated_absorpt_T_max   0.513
_shelx_estimated_absorpt_T_min   0.369
_exptl_absorpt_coefficient_mu    6.320
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.4774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1013 before and 0.0600 after correction.
The Ratio of minimum to maximum transmission is 0.6355.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.197
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.122
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon III CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            24417
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         56.956
_diffrn_reflns_theta_min         2.859
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            'Bruker CMOS Photon III '
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_current           2.86
_diffrn_source_power             0.19937059999999998
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_source_voltage           69.71
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4517
_reflns_number_total             4716
_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 (2019) V8.40A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2019) V8.40A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.787
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4716
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0266
_refine_ls_restrained_S_all      1.087
_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)+(0.0376P)²+0.8211P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0712
_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:
 C7(H7), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C),
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C)
;
_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 0.09459(2) 0.54493(2) 0.27223(2) 0.02831(7) Uani 1 1 d . . . . .
Ni1 Ni 0.24651(2) 0.53047(2) 0.26116(2) 0.02053(8) Uani 1 1 d . . . . .
P1 P 0.21761(3) 0.68843(4) 0.18680(3) 0.02246(10) Uani 1 1 d . . . . .
O1 O 0.30638(9) 0.71214(11) 0.15507(9) 0.0288(3) Uani 1 1 d . . . . .
O2 O 0.29232(9) 0.38970(11) 0.33237(9) 0.0278(3) Uani 1 1 d . . . . .
N1 N 0.24995(11) 0.34966(13) 0.39170(10) 0.0241(3) Uani 1 1 d . . . . .
H1 H 0.1946(16) 0.3950(19) 0.3765(15) 0.034(6) Uiso 1 1 d . . . . .
C1 C 0.36962(12) 0.61724(15) 0.17777(13) 0.0255(4) Uani 1 1 d . . . . .
C2 C 0.35500(13) 0.52656(15) 0.23053(13) 0.0238(3) Uani 1 1 d . . . . .
C3 C 0.42006(13) 0.43373(17) 0.25182(13) 0.0273(4) Uani 1 1 d . . . . .
H3 H 0.414170 0.371717 0.287742 0.033 Uiso 1 1 calc R U . . .
C4 C 0.49359(14) 0.43158(18) 0.22065(15) 0.0326(4) Uani 1 1 d . . . . .
H4 H 0.535693 0.368483 0.235623 0.039 Uiso 1 1 calc R U . . .
C5 C 0.50414(15) 0.52324(18) 0.16740(16) 0.0353(4) Uani 1 1 d . . . . .
H5 H 0.552866 0.521206 0.146182 0.042 Uiso 1 1 calc R U . . .
C6 C 0.44183(13) 0.61837(17) 0.14564(14) 0.0323(4) Uani 1 1 d . . . . .
H6 H 0.448519 0.680789 0.110588 0.039 Uiso 1 1 calc R U . . .
C7 C 0.22615(13) 0.81999(15) 0.25796(13) 0.0271(4) Uani 1 1 d . . . . .
H7 H 0.243589 0.883073 0.225805 0.032 Uiso 1 1 calc R U . . .
C8 C 0.31125(15) 0.80695(17) 0.36437(14) 0.0357(4) Uani 1 1 d . . . . .
H8A H 0.294815 0.748192 0.399064 0.054 Uiso 1 1 calc R U . . .
H8B H 0.321331 0.878432 0.399617 0.054 Uiso 1 1 calc R U . . .
H8C H 0.371022 0.786051 0.361224 0.054 Uiso 1 1 calc R U . . .
C9 C 0.12926(15) 0.85269(18) 0.25949(17) 0.0384(4) Uani 1 1 d . . . . .
H9A H 0.077731 0.862759 0.191966 0.058 Uiso 1 1 calc R U . . .
H9B H 0.138547 0.923076 0.296052 0.058 Uiso 1 1 calc R U . . .
H9C H 0.110615 0.792790 0.291432 0.058 Uiso 1 1 calc R U . . .
C10 C 0.10573(13) 0.69967(17) 0.06641(13) 0.0303(4) Uani 1 1 d . . . . .
H10 H 0.047959 0.696206 0.079196 0.036 Uiso 1 1 calc R U . . .
C11 C 0.10164(16) 0.5953(2) 0.00264(15) 0.0416(5) Uani 1 1 d . . . . .
H11A H 0.159293 0.594827 -0.008220 0.062 Uiso 1 1 calc R U . . .
H11B H 0.042773 0.599253 -0.060793 0.062 Uiso 1 1 calc R U . . .
H11C H 0.100306 0.526231 0.036952 0.062 Uiso 1 1 calc R U . . .
C12 C 0.09974(18) 0.8120(2) 0.01088(16) 0.0482(6) Uani 1 1 d . . . . .
H12A H 0.101538 0.875890 0.052096 0.072 Uiso 1 1 calc R U . . .
H12B H 0.038811 0.813850 -0.050766 0.072 Uiso 1 1 calc R U . . .
H12C H 0.155128 0.816737 -0.003493 0.072 Uiso 1 1 calc R U . . .
C13 C 0.21051(13) 0.22751(15) 0.36033(13) 0.0269(4) Uani 1 1 d . . . . .
C14 C 0.13156(15) 0.23403(18) 0.25082(14) 0.0344(4) Uani 1 1 d . . . . .
H14A H 0.082779 0.290726 0.243827 0.052 Uiso 1 1 calc R U . . .
H14B H 0.099883 0.160553 0.229921 0.052 Uiso 1 1 calc R U . . .
H14C H 0.162323 0.254903 0.209798 0.052 Uiso 1 1 calc R U . . .
C15 C 0.29347(15) 0.14747(18) 0.36789(17) 0.0384(4) Uani 1 1 d . . . . .
H15A H 0.335565 0.187350 0.346150 0.058 Uiso 1 1 calc R U . . .
H15B H 0.264942 0.081479 0.326031 0.058 Uiso 1 1 calc R U . . .
H15C H 0.332069 0.123236 0.436228 0.058 Uiso 1 1 calc R U . . .
C16 C 0.16353(14) 0.19059(18) 0.42611(14) 0.0348(4) Uani 1 1 d . . . . .
H16A H 0.104499 0.236547 0.409098 0.042 Uiso 1 1 calc R U . . .
H16B H 0.142859 0.111006 0.411673 0.042 Uiso 1 1 calc R U . . .
C17 C 0.23310(18) 0.2028(2) 0.53789(16) 0.0471(5) Uani 1 1 d . . . . .
H17A H 0.199053 0.179221 0.575938 0.057 Uiso 1 1 calc R U . . .
H17B H 0.290631 0.153649 0.556673 0.057 Uiso 1 1 calc R U . . .
C18 C 0.26638(19) 0.3270(2) 0.56203(15) 0.0473(5) Uani 1 1 d . . . . .
H18A H 0.311413 0.333178 0.633205 0.057 Uiso 1 1 calc R U . . .
H18B H 0.208709 0.374250 0.547924 0.057 Uiso 1 1 calc R U . . .
C19 C 0.31827(14) 0.37419(18) 0.50334(13) 0.0343(4) Uani 1 1 d . . . . .
C20 C 0.42168(15) 0.3239(2) 0.53721(18) 0.0468(5) Uani 1 1 d . . . . .
H20A H 0.419831 0.242513 0.546416 0.070 Uiso 1 1 calc R U . . .
H20B H 0.467524 0.358785 0.599414 0.070 Uiso 1 1 calc R U . . .
H20C H 0.442845 0.338768 0.487129 0.070 Uiso 1 1 calc R U . . .
C21 C 0.32707(18) 0.5048(2) 0.51339(17) 0.0472(5) Uani 1 1 d . . . . .
H21A H 0.362756 0.533085 0.479168 0.071 Uiso 1 1 calc R U . . .
H21B H 0.362196 0.525243 0.583074 0.071 Uiso 1 1 calc R U . . .
H21C H 0.261804 0.538216 0.484225 0.071 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 2.3897(3) . ?
Ni1 P1 2.0905(5) . ?
Ni1 O2 1.9045(12) . ?
Ni1 C2 1.9017(18) . ?
P1 O1 1.6449(12) . ?
P1 C7 1.8379(18) . ?
P1 C10 1.8256(18) . ?
O1 C1 1.398(2) . ?
O2 N1 1.3973(18) . ?
N1 H1 0.93(2) . ?
N1 C13 1.530(2) . ?
N1 C19 1.537(2) . ?
C1 C2 1.398(2) . ?
C1 C6 1.385(2) . ?
C2 C3 1.397(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.394(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.387(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.393(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9800 . ?
C7 C8 1.529(2) . ?
C7 C9 1.527(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10 0.9800 . ?
C10 C11 1.531(3) . ?
C10 C12 1.531(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.526(2) . ?
C13 C15 1.527(3) . ?
C13 C16 1.523(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.522(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.518(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.529(3) . ?
C19 C20 1.524(3) . ?
C19 C21 1.528(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
P1 Ni1 Br1 90.248(15) . . ?
O2 Ni1 Br1 97.74(3) . . ?
O2 Ni1 P1 171.64(4) . . ?
C2 Ni1 Br1 170.76(5) . . ?
C2 Ni1 P1 83.28(5) . . ?
C2 Ni1 O2 89.06(6) . . ?
O1 P1 Ni1 107.76(5) . . ?
O1 P1 C7 100.44(7) . . ?
O1 P1 C10 102.17(7) . . ?
C7 P1 Ni1 118.75(6) . . ?
C10 P1 Ni1 117.53(6) . . ?
C10 P1 C7 107.48(9) . . ?
C1 O1 P1 110.92(10) . . ?
N1 O2 Ni1 119.32(9) . . ?
O2 N1 H1 106.5(13) . . ?
O2 N1 C13 110.05(13) . . ?
O2 N1 C19 110.95(13) . . ?
C13 N1 H1 105.8(14) . . ?
C13 N1 C19 118.63(14) . . ?
C19 N1 H1 103.9(13) . . ?
C2 C1 O1 117.72(15) . . ?
C6 C1 O1 118.06(16) . . ?
C6 C1 C2 124.22(17) . . ?
C1 C2 Ni1 120.01(13) . . ?
C3 C2 Ni1 124.12(13) . . ?
C3 C2 C1 115.74(16) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 C2 121.74(18) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.19(19) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.08(18) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 118.02(18) . . ?
C1 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
P1 C7 H7 107.5 . . ?
C8 C7 P1 108.93(13) . . ?
C8 C7 H7 107.5 . . ?
C9 C7 P1 113.98(13) . . ?
C9 C7 H7 107.5 . . ?
C9 C7 C8 111.20(16) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
P1 C10 H10 108.0 . . ?
C11 C10 P1 108.29(14) . . ?
C11 C10 H10 108.0 . . ?
C11 C10 C12 111.23(16) . . ?
C12 C10 P1 113.29(14) . . ?
C12 C10 H10 108.0 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 N1 106.64(14) . . ?
C14 C13 C15 108.64(16) . . ?
C15 C13 N1 110.68(14) . . ?
C16 C13 N1 107.20(15) . . ?
C16 C13 C14 110.18(15) . . ?
C16 C13 C15 113.29(16) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 108.9 . . ?
C13 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 C13 113.34(16) . . ?
C17 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
C16 C17 H17A 109.7 . . ?
C16 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C18 C17 C16 109.71(17) . . ?
C18 C17 H17A 109.7 . . ?
C18 C17 H17B 109.7 . . ?
C17 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
C17 C18 C19 114.02(19) . . ?
H18A C18 H18B 107.6 . . ?
C19 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C18 C19 N1 107.20(15) . . ?
C20 C19 N1 111.34(17) . . ?
C20 C19 C18 113.13(18) . . ?
C20 C19 C21 108.65(18) . . ?
C21 C19 N1 106.06(15) . . ?
C21 C19 C18 110.22(19) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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 5.50(12) . . . . ?
Ni1 P1 C7 C8 36.15(14) . . . . ?
Ni1 P1 C7 C9 -88.67(14) . . . . ?
Ni1 P1 C10 C11 -47.30(14) . . . . ?
Ni1 P1 C10 C12 -171.18(13) . . . . ?
Ni1 O2 N1 C13 124.98(12) . . . . ?
Ni1 O2 N1 C19 -101.71(14) . . . . ?
Ni1 C2 C3 C4 174.82(14) . . . . ?
P1 O1 C1 C2 -6.24(19) . . . . ?
P1 O1 C1 C6 173.02(13) . . . . ?
O1 P1 C7 C8 -80.90(13) . . . . ?
O1 P1 C7 C9 154.28(14) . . . . ?
O1 P1 C10 C11 70.36(14) . . . . ?
O1 P1 C10 C12 -53.52(17) . . . . ?
O1 C1 C2 Ni1 4.1(2) . . . . ?
O1 C1 C2 C3 -179.81(15) . . . . ?
O1 C1 C6 C5 -179.35(16) . . . . ?
O2 N1 C13 C14 -60.73(17) . . . . ?
O2 N1 C13 C15 57.27(18) . . . . ?
O2 N1 C13 C16 -178.73(13) . . . . ?
O2 N1 C19 C18 -179.64(15) . . . . ?
O2 N1 C19 C20 -55.4(2) . . . . ?
O2 N1 C19 C21 62.61(19) . . . . ?
N1 C13 C16 C17 -53.9(2) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
C6 C1 C2 Ni1 -175.07(14) . . . . ?
C6 C1 C2 C3 1.0(3) . . . . ?
C7 P1 O1 C1 130.44(11) . . . . ?
C7 P1 C10 C11 175.57(13) . . . . ?
C7 P1 C10 C12 51.69(17) . . . . ?
C10 P1 O1 C1 -118.94(12) . . . . ?
C10 P1 C7 C8 172.67(13) . . . . ?
C10 P1 C7 C9 47.85(16) . . . . ?
C13 N1 C19 C18 -50.8(2) . . . . ?
C13 N1 C19 C20 73.4(2) . . . . ?
C13 N1 C19 C21 -168.54(16) . . . . ?
C13 C16 C17 C18 58.6(2) . . . . ?
C14 C13 C16 C17 -169.54(18) . . . . ?
C15 C13 C16 C17 68.5(2) . . . . ?
C16 C17 C18 C19 -57.6(3) . . . . ?
C17 C18 C19 N1 51.8(2) . . . . ?
C17 C18 C19 C20 -71.3(2) . . . . ?
C17 C18 C19 C21 166.78(18) . . . . ?
C19 N1 C13 C14 170.00(15) . . . . ?
C19 N1 C13 C15 -72.00(19) . . . . ?
C19 N1 C13 C16 52.00(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
####################################################################### 
# 
# 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_rajib731metjet150k
_database_code_depnum_ccdc_archive 'CCDC 2287046'
loop_
_audit_author_name
_audit_author_address
'Rajib Kumar Sarker'
;University of Montreal
Canada
;
_audit_update_record             
;
2023-08-06 deposited with the CCDC.	2024-05-24 downloaded from the CCDC.
;
_audit_creation_date             2023-08-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '4(C21 H36 Br Cl N Ni O2 P)'
_chemical_formula_sum            'C84 H144 Br4 Cl4 N4 Ni4 O8 P4'
_chemical_formula_weight         2158.18
_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 0.0137 0.0067 '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 -0.9338 1.0006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -1.3357 3.2904 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2543 0.3332 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   15.8263(4)
_cell_length_b                   11.6352(3)
_cell_length_c                   14.8354(4)
_cell_angle_alpha                90
_cell_angle_beta                 114.5960(10)
_cell_angle_gamma                90
_cell_volume                     2483.95(11)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9236
_cell_measurement_temperature    150
_cell_measurement_theta_max      54.852
_cell_measurement_theta_min      2.672
_shelx_estimated_absorpt_T_max   0.315
_shelx_estimated_absorpt_T_min   0.145
_exptl_absorpt_coefficient_mu    6.654
_exptl_absorpt_correction_T_max  0.5784
_exptl_absorpt_correction_T_min  0.2192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1489 before and 0.0859 after correction.
The Ratio of minimum to maximum transmission is 0.3790.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.472
_exptl_crystal_size_mid          0.331
_exptl_crystal_size_min          0.226
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon III CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            30401
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.921
_diffrn_reflns_theta_min         2.671
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            'Bruker CMOS Photon III '
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_current           2.86
_diffrn_source_power             0.19945639999999998
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_source_voltage           69.74
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4388
_reflns_number_total             4668
_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 (2019) V8.40A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2019) V8.40A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.908
_refine_diff_density_min         -0.960
_refine_diff_density_rms         0.125
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4668
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.095
_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)+(0.0686P)²+1.1174P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1078
_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:
 C7(H7), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C),
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.09308(2) 0.53880(2) 0.28965(2) 0.03124(12) Uani 1 1 d . . . . .
Ni1 Ni 0.22872(2) 0.52843(3) 0.44216(2) 0.01821(12) Uani 1 1 d . . . . .
Cl1 Cl 0.54055(5) 0.53702(7) 0.89287(5) 0.0423(2) Uani 1 1 d . . . . .
P1 P 0.20768(4) 0.69525(5) 0.48137(4) 0.02059(15) Uani 1 1 d . . . . .
O1 O 0.27057(12) 0.71013(14) 0.60132(12) 0.0250(4) Uani 1 1 d . . . . .
O2 O 0.27040(11) 0.38163(14) 0.42223(12) 0.0238(4) Uani 1 1 d . . . . .
N1 N 0.23139(13) 0.32892(17) 0.32898(14) 0.0199(4) Uani 1 1 d . . . . .
H1 H 0.181(2) 0.367(3) 0.294(2) 0.024(7) Uiso 1 1 d . . . . .
C1 C 0.33250(15) 0.6195(2) 0.63687(16) 0.0221(5) Uani 1 1 d . . . . .
C2 C 0.32679(17) 0.52918(18) 0.57212(18) 0.0208(5) Uani 1 1 d . . . . .
C3 C 0.39229(16) 0.4426(2) 0.61086(18) 0.0240(5) Uani 1 1 d . . . . .
H3 H 0.392323 0.382065 0.569921 0.029 Uiso 1 1 calc R U . . .
C4 C 0.45842(17) 0.4431(2) 0.70958(18) 0.0268(5) Uani 1 1 d . . . . .
H4 H 0.500945 0.383396 0.734221 0.032 Uiso 1 1 calc R U . . .
C5 C 0.45907(17) 0.5346(2) 0.76970(18) 0.0260(6) Uani 1 1 d . . . . .
C6 C 0.39772(16) 0.6251(2) 0.73462(17) 0.0246(5) Uani 1 1 d . . . . .
H6 H 0.399970 0.687439 0.774831 0.030 Uiso 1 1 calc R U . . .
C7 C 0.09384(17) 0.7417(2) 0.47024(19) 0.0301(6) Uani 1 1 d . . . . .
H7 H 0.052761 0.744736 0.399364 0.036 Uiso 1 1 calc R U . . .
C8 C 0.0550(2) 0.6507(3) 0.5167(2) 0.0415(7) Uani 1 1 d . . . . .
H8A H 0.055344 0.577243 0.487365 0.062 Uiso 1 1 calc R U . . .
H8B H -0.007591 0.670450 0.505201 0.062 Uiso 1 1 calc R U . . .
H8C H 0.092679 0.647072 0.586741 0.062 Uiso 1 1 calc R U . . .
C9 C 0.0934(2) 0.8612(3) 0.5131(3) 0.0510(8) Uani 1 1 d . . . . .
H9A H 0.134712 0.861942 0.582227 0.076 Uiso 1 1 calc R U . . .
H9B H 0.031593 0.879586 0.505297 0.076 Uiso 1 1 calc R U . . .
H9C H 0.113576 0.917014 0.478606 0.076 Uiso 1 1 calc R U . . .
C10 C 0.25451(19) 0.8102(2) 0.43153(19) 0.0297(5) Uani 1 1 d . . . . .
H10 H 0.253681 0.881238 0.466703 0.036 Uiso 1 1 calc R U . . .
C11 C 0.3556(2) 0.7836(3) 0.4532(2) 0.0384(6) Uani 1 1 d . . . . .
H11A H 0.388733 0.764222 0.521966 0.058 Uiso 1 1 calc R U . . .
H11B H 0.383605 0.849821 0.438235 0.058 Uiso 1 1 calc R U . . .
H11C H 0.357890 0.720080 0.413020 0.058 Uiso 1 1 calc R U . . .
C12 C 0.1963(2) 0.8308(3) 0.3210(2) 0.0436(7) Uani 1 1 d . . . . .
H12A H 0.195312 0.762099 0.284672 0.065 Uiso 1 1 calc R U . . .
H12B H 0.222974 0.892404 0.298475 0.065 Uiso 1 1 calc R U . . .
H12C H 0.133952 0.850680 0.310318 0.065 Uiso 1 1 calc R U . . .
C13 C 0.29826(17) 0.3371(2) 0.2776(2) 0.0293(5) Uani 1 1 d . . . . .
C14 C 0.39338(18) 0.2885(3) 0.3431(2) 0.0387(7) Uani 1 1 d . . . . .
H14A H 0.410700 0.312695 0.410295 0.058 Uiso 1 1 calc R U . . .
H14B H 0.438360 0.316005 0.320402 0.058 Uiso 1 1 calc R U . . .
H14C H 0.391138 0.206069 0.339859 0.058 Uiso 1 1 calc R U . . .
C15 C 0.3077(3) 0.4656(2) 0.2612(3) 0.0444(8) Uani 1 1 d . . . . .
H15A H 0.247096 0.498834 0.227460 0.067 Uiso 1 1 calc R U . . .
H15B H 0.342376 0.475636 0.221875 0.067 Uiso 1 1 calc R U . . .
H15C H 0.339697 0.502826 0.324150 0.067 Uiso 1 1 calc R U . . .
C16 C 0.2517(2) 0.2750(3) 0.1781(2) 0.0376(6) Uani 1 1 d . . . . .
H16A H 0.198882 0.320164 0.134770 0.045 Uiso 1 1 calc R U . . .
H16B H 0.295363 0.270962 0.147799 0.045 Uiso 1 1 calc R U . . .
C17 C 0.21863(18) 0.1544(3) 0.1852(2) 0.0357(6) Uani 1 1 d . . . . .
H17A H 0.271316 0.106447 0.224320 0.043 Uiso 1 1 calc R U . . .
H17B H 0.188529 0.121204 0.119420 0.043 Uiso 1 1 calc R U . . .
C18 C 0.15078(17) 0.1588(2) 0.23319(19) 0.0310(6) Uani 1 1 d . . . . .
H18A H 0.129999 0.081350 0.237263 0.037 Uiso 1 1 calc R U . . .
H18B H 0.096828 0.203192 0.191212 0.037 Uiso 1 1 calc R U . . .
C19 C 0.19167(17) 0.2117(2) 0.33719(18) 0.0251(5) Uani 1 1 d . . . . .
C20 C 0.2664(2) 0.1361(2) 0.4135(2) 0.0348(6) Uani 1 1 d . . . . .
H20A H 0.303298 0.101063 0.383508 0.052 Uiso 1 1 calc R U . . .
H20B H 0.237268 0.077297 0.436145 0.052 Uiso 1 1 calc R U . . .
H20C H 0.305430 0.182359 0.468698 0.052 Uiso 1 1 calc R U . . .
C21 C 0.11549(19) 0.2344(2) 0.3721(2) 0.0333(6) Uani 1 1 d . . . . .
H21A H 0.142347 0.266374 0.437695 0.050 Uiso 1 1 calc R U . . .
H21B H 0.084686 0.163595 0.372843 0.050 Uiso 1 1 calc R U . . .
H21C H 0.071338 0.287659 0.327786 0.050 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 2.3872(4) . ?
Ni1 P1 2.0924(6) . ?
Ni1 O2 1.8981(16) . ?
Ni1 C2 1.907(2) . ?
Cl1 C5 1.744(3) . ?
P1 O1 1.6471(16) . ?
P1 C7 1.821(3) . ?
P1 C10 1.828(3) . ?
O1 C1 1.386(3) . ?
O2 N1 1.400(2) . ?
N1 H1 0.87(3) . ?
N1 C13 1.544(3) . ?
N1 C19 1.527(3) . ?
C1 C2 1.401(3) . ?
C1 C6 1.388(3) . ?
C2 C3 1.387(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.402(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.386(4) . ?
C5 C6 1.379(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9800 . ?
C7 C8 1.526(4) . ?
C7 C9 1.530(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10 0.9800 . ?
C10 C11 1.526(4) . ?
C10 C12 1.529(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.521(4) . ?
C13 C15 1.532(4) . ?
C13 C16 1.529(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.516(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.517(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.532(3) . ?
C19 C20 1.530(3) . ?
C19 C21 1.520(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
P1 Ni1 Br1 91.847(19) . . ?
O2 Ni1 Br1 97.56(5) . . ?
O2 Ni1 P1 169.73(5) . . ?
O2 Ni1 C2 88.41(8) . . ?
C2 Ni1 Br1 172.14(8) . . ?
C2 Ni1 P1 82.61(7) . . ?
O1 P1 Ni1 107.66(6) . . ?
O1 P1 C7 101.35(11) . . ?
O1 P1 C10 101.29(10) . . ?
C7 P1 Ni1 121.06(9) . . ?
C7 P1 C10 107.36(13) . . ?
C10 P1 Ni1 115.36(9) . . ?
C1 O1 P1 110.17(14) . . ?
N1 O2 Ni1 120.61(13) . . ?
O2 N1 H1 106.7(19) . . ?
O2 N1 C13 110.50(17) . . ?
O2 N1 C19 109.83(17) . . ?
C13 N1 H1 107.9(19) . . ?
C19 N1 H1 102.0(19) . . ?
C19 N1 C13 118.93(19) . . ?
O1 C1 C2 118.45(19) . . ?
O1 C1 C6 117.5(2) . . ?
C6 C1 C2 124.0(2) . . ?
C1 C2 Ni1 119.32(17) . . ?
C3 C2 Ni1 124.69(18) . . ?
C3 C2 C1 115.9(2) . . ?
C2 C3 H3 118.9 . . ?
C2 C3 C4 122.3(2) . . ?
C4 C3 H3 118.9 . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.6(2) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 Cl1 119.40(19) . . ?
C6 C5 Cl1 118.71(19) . . ?
C6 C5 C4 121.9(2) . . ?
C1 C6 H6 121.3 . . ?
C5 C6 C1 117.3(2) . . ?
C5 C6 H6 121.3 . . ?
P1 C7 H7 107.3 . . ?
C8 C7 P1 108.82(19) . . ?
C8 C7 H7 107.3 . . ?
C8 C7 C9 111.8(3) . . ?
C9 C7 P1 114.0(2) . . ?
C9 C7 H7 107.3 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
P1 C10 H10 107.7 . . ?
C11 C10 P1 109.38(18) . . ?
C11 C10 H10 107.7 . . ?
C11 C10 C12 111.6(2) . . ?
C12 C10 P1 112.54(19) . . ?
C12 C10 H10 107.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 N1 111.2(2) . . ?
C14 C13 C15 109.1(2) . . ?
C14 C13 C16 113.1(2) . . ?
C15 C13 N1 105.7(2) . . ?
C16 C13 N1 107.1(2) . . ?
C16 C13 C15 110.4(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 108.7 . . ?
C13 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C17 C16 C13 114.3(2) . . ?
C17 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
C16 C17 H17A 109.8 . . ?
C16 C17 H17B 109.8 . . ?
C16 C17 C18 109.5(2) . . ?
H17A C17 H17B 108.2 . . ?
C18 C17 H17A 109.8 . . ?
C18 C17 H17B 109.8 . . ?
C17 C18 H18A 108.8 . . ?
C17 C18 H18B 108.8 . . ?
C17 C18 C19 113.7(2) . . ?
H18A C18 H18B 107.7 . . ?
C19 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
N1 C19 C18 107.1(2) . . ?
N1 C19 C20 110.8(2) . . ?
C20 C19 C18 112.7(2) . . ?
C21 C19 N1 106.44(19) . . ?
C21 C19 C18 110.5(2) . . ?
C21 C19 C20 109.0(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
Br1 Ni1 O2 N1 12.12(15) . . . . ?
Ni1 P1 O1 C1 12.32(16) . . . . ?
Ni1 P1 C7 C8 47.9(2) . . . . ?
Ni1 P1 C7 C9 173.36(19) . . . . ?
Ni1 P1 C10 C11 -50.2(2) . . . . ?
Ni1 P1 C10 C12 74.5(2) . . . . ?
Ni1 O2 N1 C13 104.19(18) . . . . ?
Ni1 O2 N1 C19 -122.67(16) . . . . ?
Ni1 C2 C3 C4 -174.77(19) . . . . ?
Cl1 C5 C6 C1 -178.70(18) . . . . ?
P1 Ni1 O2 N1 -144.1(3) . . . . ?
P1 O1 C1 C2 -5.7(3) . . . . ?
P1 O1 C1 C6 173.21(17) . . . . ?
O1 P1 C7 C8 -70.97(19) . . . . ?
O1 P1 C7 C9 54.5(2) . . . . ?
O1 P1 C10 C11 65.73(19) . . . . ?
O1 P1 C10 C12 -169.6(2) . . . . ?
O1 C1 C2 Ni1 -5.0(3) . . . . ?
O1 C1 C2 C3 178.1(2) . . . . ?
O1 C1 C6 C5 179.9(2) . . . . ?
O2 N1 C13 C14 54.5(3) . . . . ?
O2 N1 C13 C15 -63.8(3) . . . . ?
O2 N1 C13 C16 178.50(19) . . . . ?
O2 N1 C19 C18 -179.70(18) . . . . ?
O2 N1 C19 C20 -56.4(3) . . . . ?
O2 N1 C19 C21 62.1(2) . . . . ?
N1 C13 C16 C17 -51.7(3) . . . . ?
C1 C2 C3 C4 2.0(4) . . . . ?
C2 Ni1 O2 N1 -173.02(16) . . . . ?
C2 C1 C6 C5 -1.3(4) . . . . ?
C2 C3 C4 C5 -1.2(4) . . . . ?
C3 C4 C5 Cl1 179.87(19) . . . . ?
C3 C4 C5 C6 -1.0(4) . . . . ?
C4 C5 C6 C1 2.2(4) . . . . ?
C6 C1 C2 Ni1 176.20(18) . . . . ?
C6 C1 C2 C3 -0.7(4) . . . . ?
C7 P1 O1 C1 140.36(16) . . . . ?
C7 P1 C10 C11 171.56(18) . . . . ?
C7 P1 C10 C12 -63.8(2) . . . . ?
C10 P1 O1 C1 -109.14(16) . . . . ?
C10 P1 C7 C8 -176.74(18) . . . . ?
C10 P1 C7 C9 -51.2(2) . . . . ?
C13 N1 C19 C18 -51.0(3) . . . . ?
C13 N1 C19 C20 72.3(3) . . . . ?
C13 N1 C19 C21 -169.3(2) . . . . ?
C13 C16 C17 C18 58.0(3) . . . . ?
C14 C13 C16 C17 71.1(3) . . . . ?
C15 C13 C16 C17 -166.3(2) . . . . ?
C16 C17 C18 C19 -58.6(3) . . . . ?
C17 C18 C19 N1 53.5(3) . . . . ?
C17 C18 C19 C20 -68.7(3) . . . . ?
C17 C18 C19 C21 169.0(2) . . . . ?
C19 N1 C13 C14 -73.9(3) . . . . ?
C19 N1 C13 C15 167.8(2) . . . . ?
C19 N1 C13 C16 50.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
####################################################################### 
# 
# 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_rajib931
_database_code_depnum_ccdc_archive 'CCDC 2287050'
loop_
_audit_author_name
_audit_author_address
'Rajib Kumar Sarker'
;University of Montreal
Canada
;
_audit_update_record             
;
2023-08-06 deposited with the CCDC.	2024-05-24 downloaded from the CCDC.
;
_audit_creation_date             2023-08-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C18 H26 N4 Ni O P, C3 H4 N2'
_chemical_formula_sum            'C21 H30 Br N6 Ni O P'
_chemical_formula_weight         552.10
_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 0.0137 0.0067 '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 -0.9338 1.0006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -1.3357 3.2904 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2543 0.3332 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.1454(4)
_cell_length_b                   27.5501(11)
_cell_length_c                   9.8982(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.159(2)
_cell_angle_gamma                90
_cell_volume                     2437.97(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5155
_cell_measurement_temperature    150
_cell_measurement_theta_max      54.925
_cell_measurement_theta_min      4.525
_shelx_estimated_absorpt_T_max   0.613
_shelx_estimated_absorpt_T_min   0.533
_exptl_absorpt_coefficient_mu    6.154
_exptl_absorpt_correction_T_max  0.200601
_exptl_absorpt_correction_T_min  0.094568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1447 before and 0.0849 after correction.
 
For component 2:
 wR2(int) was 0.1580 before and 0.0881 after correction.
 The Ratio of minimum to maximum transmission is 0.47.

Final HKLF 4 output contains 42514 reflections, Rint = 0.0682
 (34591 with I > 3sig(I), Rint = 0.0664)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.117
_exptl_crystal_size_mid          0.099
_exptl_crystal_size_min          0.088
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon III CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4567
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.900
_diffrn_reflns_theta_min         4.524
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            'Bruker CMOS Photon III '
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_current           2.86
_diffrn_source_power             0.19937059999999998
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_source_voltage           69.71
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4351
_reflns_number_total             4567
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 4 (2022) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.613
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4567
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.065
_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)+(0.0777P)²+0.6710P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1149
_refine_special_details          'Refined as a 2-component twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.733(3)
 0.267(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10)
3.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N4(H4), C3(H3), C4(H4A), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15),
  C16(H16), C17(H17), C18(H18), N6(H6A), C19(H19), C20(H20), C21(H21)
3.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_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
Br1 Br 0.82316(3) 0.64743(2) 0.47731(3) 0.04473(13) Uani 1 1 d . . . . .
Ni1 Ni 0.26821(4) 0.56592(2) 0.09752(3) 0.03138(13) Uani 1 1 d . . . . .
P1 P 0.24202(7) 0.62711(2) -0.03544(6) 0.03273(16) Uani 1 1 d . . . . .
O1 O 0.1957(2) 0.60691(6) -0.19408(17) 0.0397(4) Uani 1 1 d . . . . .
N1 N 0.2994(2) 0.50807(8) 0.2098(2) 0.0351(4) Uani 1 1 d . . . . .
N2 N 0.2714(3) 0.44538(9) 0.3371(3) 0.0512(6) Uani 1 1 d . . . . .
H2 H 0.227957 0.422234 0.375695 0.061 Uiso 1 1 calc R U . . .
N3 N 0.2921(2) 0.60357(7) 0.2668(2) 0.0361(4) Uani 1 1 d . . . . .
N4 N 0.3735(3) 0.64480(8) 0.4585(2) 0.0411(5) Uani 1 1 d . . . . .
H4 H 0.433777 0.661277 0.523458 0.049 Uiso 1 1 calc R U . . .
C1 C 0.1944(3) 0.55636(9) -0.1989(3) 0.0348(5) Uani 1 1 d . . . . .
C2 C 0.2291(3) 0.53094(9) -0.0738(3) 0.0341(5) Uani 1 1 d . . . . .
C3 C 0.2287(3) 0.48017(10) -0.0867(3) 0.0381(5) Uani 1 1 d . . . . .
H3 H 0.251957 0.460800 -0.005607 0.046 Uiso 1 1 calc R U . . .
C4 C 0.1949(3) 0.45741(10) -0.2156(3) 0.0408(6) Uani 1 1 d . . . . .
H4A H 0.197490 0.422999 -0.220703 0.049 Uiso 1 1 calc R U . . .
C5 C 0.1580(3) 0.48411(10) -0.3348(3) 0.0405(6) Uani 1 1 d . . . . .
H5 H 0.132497 0.468249 -0.421799 0.049 Uiso 1 1 calc R U . . .
C6 C 0.1581(3) 0.53471(10) -0.3277(3) 0.0396(5) Uani 1 1 d . . . . .
H6 H 0.133933 0.553797 -0.409253 0.047 Uiso 1 1 calc R U . . .
C7 C 0.4079(3) 0.66283(10) -0.0428(3) 0.0416(6) Uani 1 1 d . . . . .
H7 H 0.388851 0.679320 -0.134852 0.050 Uiso 1 1 calc R U . . .
C8 C 0.5386(4) 0.62789(14) -0.0389(6) 0.0755(12) Uani 1 1 d . . . . .
H8A H 0.563468 0.612045 0.051707 0.113 Uiso 1 1 calc R U . . .
H8B H 0.625714 0.645980 -0.054746 0.113 Uiso 1 1 calc R U . . .
H8C H 0.510390 0.603254 -0.111080 0.113 Uiso 1 1 calc R U . . .
C9 C 0.4438(4) 0.70257(12) 0.0675(3) 0.0557(8) Uani 1 1 d . . . . .
H9A H 0.359411 0.725192 0.056965 0.084 Uiso 1 1 calc R U . . .
H9B H 0.533645 0.720178 0.056527 0.084 Uiso 1 1 calc R U . . .
H9C H 0.461129 0.687765 0.159512 0.084 Uiso 1 1 calc R U . . .
C10 C 0.0925(3) 0.66980(9) -0.0273(3) 0.0379(5) Uani 1 1 d . . . . .
H10 H 0.117983 0.686458 0.064465 0.045 Uiso 1 1 calc R U . . .
C11 C -0.0533(3) 0.64224(12) -0.0341(4) 0.0531(7) Uani 1 1 d . . . . .
H11A H -0.084391 0.627177 -0.125308 0.080 Uiso 1 1 calc R U . . .
H11B H -0.130972 0.664810 -0.018620 0.080 Uiso 1 1 calc R U . . .
H11C H -0.038309 0.617011 0.037306 0.080 Uiso 1 1 calc R U . . .
C12 C 0.0745(3) 0.70923(10) -0.1402(3) 0.0472(6) Uani 1 1 d . . . . .
H12A H 0.165282 0.729128 -0.126146 0.071 Uiso 1 1 calc R U . . .
H12B H -0.011436 0.729841 -0.134860 0.071 Uiso 1 1 calc R U . . .
H12C H 0.058249 0.693776 -0.231310 0.071 Uiso 1 1 calc R U . . .
C13 C 0.2021(3) 0.47958(10) 0.2501(3) 0.0451(6) Uani 1 1 d . . . . .
H13 H 0.096604 0.482724 0.221692 0.054 Uiso 1 1 calc R U . . .
C14 C 0.4196(4) 0.45297(13) 0.3543(4) 0.0635(9) Uani 1 1 d . . . . .
H14 H 0.496862 0.434780 0.411500 0.076 Uiso 1 1 calc R U . . .
C15 C 0.4373(3) 0.49153(11) 0.2745(3) 0.0530(7) Uani 1 1 d . . . . .
H15 H 0.530349 0.504893 0.264936 0.064 Uiso 1 1 calc R U . . .
C16 C 0.1779(3) 0.60791(10) 0.3392(3) 0.0409(6) Uani 1 1 d . . . . .
H16 H 0.079793 0.595089 0.310519 0.049 Uiso 1 1 calc R U . . .
C17 C 0.2285(3) 0.63331(10) 0.4570(3) 0.0442(6) Uani 1 1 d . . . . .
H17 H 0.173446 0.641489 0.525145 0.053 Uiso 1 1 calc R U . . .
C18 C 0.4086(3) 0.62654(9) 0.3431(3) 0.0395(5) Uani 1 1 d . . . . .
H18 H 0.503653 0.629641 0.319451 0.047 Uiso 1 1 calc R U . . .
N5 N -0.0112(3) 0.78064(9) 0.1413(2) 0.0455(5) Uani 1 1 d . . . . .
N6 N -0.0018(3) 0.72284(8) 0.2965(2) 0.0440(5) Uani 1 1 d . . . . .
H6A H -0.030284 0.699274 0.345241 0.053 Uiso 1 1 calc R U . . .
C19 C 0.1397(3) 0.74136(10) 0.3116(3) 0.0468(6) Uani 1 1 d . . . . .
H19 H 0.226205 0.731389 0.376829 0.056 Uiso 1 1 calc R U . . .
C20 C 0.1322(3) 0.77642(10) 0.2159(3) 0.0452(6) Uani 1 1 d . . . . .
H20 H 0.214366 0.795464 0.202045 0.054 Uiso 1 1 calc R U . . .
C21 C -0.0886(3) 0.74754(10) 0.1933(3) 0.0443(6) Uani 1 1 d . . . . .
H21 H -0.192658 0.741982 0.161473 0.053 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 2.1210(7) . ?
Ni1 N1 1.930(2) . ?
Ni1 N3 1.944(2) . ?
Ni1 C2 1.918(2) . ?
P1 O1 1.6354(18) . ?
P1 C7 1.823(3) . ?
P1 C10 1.818(3) . ?
O1 C1 1.394(3) . ?
N1 C13 1.311(3) . ?
N1 C15 1.366(4) . ?
N2 H2 0.8800 . ?
N2 C13 1.342(4) . ?
N2 C14 1.346(5) . ?
N3 C16 1.390(3) . ?
N3 C18 1.330(3) . ?
N4 H4 0.8800 . ?
N4 C17 1.361(4) . ?
N4 C18 1.348(4) . ?
C1 C2 1.399(3) . ?
C1 C6 1.383(4) . ?
C2 C3 1.405(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.396(4) . ?
C4 H4A 0.9500 . ?
C4 C5 1.371(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.396(4) . ?
C6 H6 0.9500 . ?
C7 H7 1.0000 . ?
C7 C8 1.529(4) . ?
C7 C9 1.532(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10 1.0000 . ?
C10 C11 1.523(4) . ?
C10 C12 1.543(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.354(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.355(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
N5 C20 1.368(4) . ?
N5 C21 1.323(4) . ?
N6 H6A 0.8800 . ?
N6 C19 1.370(4) . ?
N6 C21 1.340(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.345(4) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ni1 P1 176.01(6) . . ?
N1 Ni1 N3 88.18(8) . . ?
N3 Ni1 P1 95.07(6) . . ?
C2 Ni1 P1 82.82(8) . . ?
C2 Ni1 N1 94.11(10) . . ?
C2 Ni1 N3 175.45(9) . . ?
O1 P1 Ni1 107.33(7) . . ?
O1 P1 C7 101.23(12) . . ?
O1 P1 C10 102.58(11) . . ?
C7 P1 Ni1 117.89(9) . . ?
C10 P1 Ni1 118.30(9) . . ?
C10 P1 C7 107.03(12) . . ?
C1 O1 P1 111.81(15) . . ?
C13 N1 Ni1 129.98(19) . . ?
C13 N1 C15 106.1(2) . . ?
C15 N1 Ni1 123.72(18) . . ?
C13 N2 H2 126.3 . . ?
C13 N2 C14 107.4(3) . . ?
C14 N2 H2 126.3 . . ?
C16 N3 Ni1 122.00(17) . . ?
C18 N3 Ni1 132.39(19) . . ?
C18 N3 C16 105.5(2) . . ?
C17 N4 H4 126.0 . . ?
C18 N4 H4 126.0 . . ?
C18 N4 C17 108.1(2) . . ?
O1 C1 C2 118.1(2) . . ?
C6 C1 O1 117.5(2) . . ?
C6 C1 C2 124.4(2) . . ?
C1 C2 Ni1 119.75(19) . . ?
C1 C2 C3 115.0(2) . . ?
C3 C2 Ni1 125.25(19) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 C2 121.7(2) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4A 119.6 . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4A 119.6 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.7(2) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 118.3(2) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
P1 C7 H7 107.1 . . ?
C8 C7 P1 108.2(2) . . ?
C8 C7 H7 107.1 . . ?
C8 C7 C9 112.5(3) . . ?
C9 C7 P1 114.3(2) . . ?
C9 C7 H7 107.1 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
P1 C10 H10 107.7 . . ?
C11 C10 P1 109.58(19) . . ?
C11 C10 H10 107.7 . . ?
C11 C10 C12 111.1(2) . . ?
C12 C10 P1 112.93(18) . . ?
C12 C10 H10 107.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 N2 110.9(3) . . ?
N1 C13 H13 124.6 . . ?
N2 C13 H13 124.6 . . ?
N2 C14 H14 126.6 . . ?
N2 C14 C15 106.8(3) . . ?
C15 C14 H14 126.6 . . ?
N1 C15 H15 125.6 . . ?
C14 C15 N1 108.8(3) . . ?
C14 C15 H15 125.6 . . ?
N3 C16 H16 125.4 . . ?
C17 C16 N3 109.3(2) . . ?
C17 C16 H16 125.4 . . ?
N4 C17 H17 126.7 . . ?
C16 C17 N4 106.6(2) . . ?
C16 C17 H17 126.7 . . ?
N3 C18 N4 110.6(2) . . ?
N3 C18 H18 124.7 . . ?
N4 C18 H18 124.7 . . ?
C21 N5 C20 105.2(2) . . ?
C19 N6 H6A 126.6 . . ?
C21 N6 H6A 126.6 . . ?
C21 N6 C19 106.7(2) . . ?
N6 C19 H19 126.8 . . ?
C20 C19 N6 106.5(3) . . ?
C20 C19 H19 126.8 . . ?
N5 C20 H20 125.0 . . ?
C19 C20 N5 110.0(3) . . ?
C19 C20 H20 125.0 . . ?
N5 C21 N6 111.6(3) . . ?
N5 C21 H21 124.2 . . ?
N6 C21 H21 124.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ni1 P1 O1 C1 -3.30(18) . . . . ?
Ni1 P1 C7 C8 39.5(3) . . . . ?
Ni1 P1 C7 C9 -86.7(2) . . . . ?
Ni1 P1 C10 C11 -49.0(2) . . . . ?
Ni1 P1 C10 C12 -173.45(16) . . . . ?
Ni1 N1 C13 N2 -174.81(18) . . . . ?
Ni1 N1 C15 C14 174.5(2) . . . . ?
Ni1 N3 C16 C17 175.98(18) . . . . ?
Ni1 N3 C18 N4 -175.34(17) . . . . ?
Ni1 C2 C3 C4 178.17(19) . . . . ?
P1 O1 C1 C2 0.8(3) . . . . ?
P1 O1 C1 C6 -179.44(19) . . . . ?
O1 P1 C7 C8 -77.1(3) . . . . ?
O1 P1 C7 C9 156.6(2) . . . . ?
O1 P1 C10 C11 68.8(2) . . . . ?
O1 P1 C10 C12 -55.6(2) . . . . ?
O1 C1 C2 Ni1 2.6(3) . . . . ?
O1 C1 C2 C3 -178.7(2) . . . . ?
O1 C1 C6 C5 179.2(2) . . . . ?
N2 C14 C15 N1 0.9(4) . . . . ?
N3 C16 C17 N4 0.0(3) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C2 C1 C6 C5 -1.0(4) . . . . ?
C2 C3 C4 C5 -1.2(4) . . . . ?
C3 C4 C5 C6 1.8(4) . . . . ?
C4 C5 C6 C1 -0.7(4) . . . . ?
C6 C1 C2 Ni1 -177.1(2) . . . . ?
C6 C1 C2 C3 1.5(4) . . . . ?
C7 P1 O1 C1 120.86(18) . . . . ?
C7 P1 C10 C11 174.9(2) . . . . ?
C7 P1 C10 C12 50.5(2) . . . . ?
C10 P1 O1 C1 -128.64(17) . . . . ?
C10 P1 C7 C8 175.8(3) . . . . ?
C10 P1 C7 C9 49.6(2) . . . . ?
C13 N1 C15 C14 -0.4(4) . . . . ?
C13 N2 C14 C15 -1.2(4) . . . . ?
C14 N2 C13 N1 1.0(4) . . . . ?
C15 N1 C13 N2 -0.4(3) . . . . ?
C16 N3 C18 N4 0.1(3) . . . . ?
C17 N4 C18 N3 -0.1(3) . . . . ?
C18 N3 C16 C17 0.0(3) . . . . ?
C18 N4 C17 C16 0.1(3) . . . . ?
N6 C19 C20 N5 0.4(3) . . . . ?
C19 N6 C21 N5 0.1(3) . . . . ?
C20 N5 C21 N6 0.1(3) . . . . ?
C21 N5 C20 C19 -0.3(3) . . . . ?
C21 N6 C19 C20 -0.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.733(3)
2 0.267(3)

_chemical_properties_physical    Air-sensitive,Moisture-sensitive
####################################################################### 
# 
# 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_rajib741
_database_code_depnum_ccdc_archive 'CCDC 2287048'
loop_
_audit_author_name
_audit_author_address
'Rajib Kumar Sarker'
;University of Montreal
Canada
;
_audit_update_record             
;
2024-02-13 deposited with the CCDC.	2024-05-24 downloaded from the CCDC.
;
_audit_creation_date             2024-02-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H40 Br N Ni O3 P'
_chemical_formula_sum            'C26 H40 Br N Ni O3 P'
_chemical_formula_weight         584.18
_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 0.0137 0.0067 '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 -0.9338 1.0006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -1.3357 3.2904 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2543 0.3332 '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                   12.4164(6)
_cell_length_b                   16.3578(8)
_cell_length_c                   14.9046(7)
_cell_angle_alpha                90
_cell_angle_beta                 112.769(2)
_cell_angle_gamma                90
_cell_volume                     2791.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9929
_cell_measurement_temperature    150
_cell_measurement_theta_max      54.904
_cell_measurement_theta_min      2.798
_shelx_estimated_absorpt_T_max   0.363
_shelx_estimated_absorpt_T_min   0.229
_exptl_absorpt_coefficient_mu    5.394
_exptl_absorpt_correction_T_max  0.1540
_exptl_absorpt_correction_T_min  0.0446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1635 before and 0.1062 after correction.
The Ratio of minimum to maximum transmission is 0.2896.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1220
_exptl_crystal_size_max          0.388
_exptl_crystal_size_mid          0.354
_exptl_crystal_size_min          0.236
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon III CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20919
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.922
_diffrn_reflns_theta_min         3.655
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            'Bruker CMOS Photon III '
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_current           2.85
_diffrn_source_power             0.1986735
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_source_voltage           69.71
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4930
_reflns_number_total             5133
_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 () ; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 4 (2022) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT () ; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         2.010
_refine_diff_density_min         -1.100
_refine_diff_density_rms         0.158
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5133
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0678
_refine_ls_restrained_S_all      1.044
_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)+(0.1444P)²+0.6759P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1716
_refine_ls_wR_factor_ref         0.1735
_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:
 C12(H12), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C25(H25A,H25B), C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C10(H10)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C16(H16A,H16B,
 H16C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C23(H23A,
 H23B,H23C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.57221(3) 0.18088(2) 0.45796(2) 0.04231(18) Uani 1 1 d . . . . .
Ni1 Ni 0.55053(3) 0.27627(2) 0.57017(3) 0.03285(19) Uani 1 1 d . . . . .
P1 P 0.39175(7) 0.22288(4) 0.55807(6) 0.0350(2) Uani 1 1 d . . . . .
O1 O 0.68909(19) 0.33770(15) 0.59215(18) 0.0419(5) Uani 1 1 d . . . . .
O2 O 0.3340(2) 0.28145(13) 0.61677(18) 0.0406(5) Uani 1 1 d . . . . .
O3 O 0.64818(19) 0.51496(14) 0.83605(17) 0.0431(5) Uani 1 1 d . . . . .
N1 N 0.7511(2) 0.32916(16) 0.5314(2) 0.0372(6) Uani 1 1 d . . . . .
C1 C 0.5182(3) 0.34686(18) 0.6575(2) 0.0353(6) Uani 1 1 d . . . . .
C2 C 0.4157(2) 0.34013(18) 0.6715(2) 0.0339(6) Uani 1 1 d . . . . .
C3 C 0.3880(3) 0.38543(18) 0.7404(2) 0.0354(6) Uani 1 1 d . . . . .
C4 C 0.2851(3) 0.3725(2) 0.7577(3) 0.0445(7) Uani 1 1 d . . . . .
H4 H 0.230793 0.333806 0.721364 0.053 Uiso 1 1 calc R U . . .
C5 C 0.2651(3) 0.4164(2) 0.8275(3) 0.0487(8) Uani 1 1 d . . . . .
H5 H 0.197616 0.406765 0.838876 0.058 Uiso 1 1 calc R U . . .
C6 C 0.3448(3) 0.4759(2) 0.8824(3) 0.0461(7) Uani 1 1 d . . . . .
H6 H 0.329978 0.505388 0.929814 0.055 Uiso 1 1 calc R U . . .
C7 C 0.4445(3) 0.4906(2) 0.8661(2) 0.0407(7) Uani 1 1 d . . . . .
H7 H 0.496421 0.530745 0.901942 0.049 Uiso 1 1 calc R U . . .
C8 C 0.4694(2) 0.44556(17) 0.7957(2) 0.0343(6) Uani 1 1 d . . . . .
C9 C 0.5741(3) 0.45565(18) 0.7794(2) 0.0355(6) Uani 1 1 d . . . . .
C10 C 0.5984(3) 0.40793(18) 0.7143(2) 0.0353(6) Uani 1 1 d . . . . .
H10 H 0.668613 0.415291 0.706580 0.042 Uiso 1 1 calc R U . . .
C11 C 0.7456(3) 0.5359(2) 0.8133(3) 0.0470(7) Uani 1 1 d . . . . .
H11A H 0.718780 0.553990 0.746951 0.071 Uiso 1 1 calc R U . . .
H11B H 0.794935 0.488966 0.821983 0.071 Uiso 1 1 calc R U . . .
H11C H 0.788858 0.579047 0.855620 0.071 Uiso 1 1 calc R U . . .
C12 C 0.3895(3) 0.12412(19) 0.6164(2) 0.0404(7) Uani 1 1 d . . . . .
H12 H 0.312895 0.119064 0.620388 0.049 Uiso 1 1 calc R U . . .
C13 C 0.4805(4) 0.1240(3) 0.7199(3) 0.0577(9) Uani 1 1 d . . . . .
H13A H 0.557234 0.124965 0.718685 0.087 Uiso 1 1 calc R U . . .
H13B H 0.471744 0.075529 0.752822 0.087 Uiso 1 1 calc R U . . .
H13C H 0.470053 0.171349 0.753719 0.087 Uiso 1 1 calc R U . . .
C14 C 0.4039(3) 0.0510(2) 0.5593(3) 0.0474(8) Uani 1 1 d . . . . .
H14A H 0.337354 0.047075 0.498868 0.071 Uiso 1 1 calc R U . . .
H14B H 0.410032 0.002069 0.596506 0.071 Uiso 1 1 calc R U . . .
H14C H 0.473371 0.057606 0.546354 0.071 Uiso 1 1 calc R U . . .
C15 C 0.2756(3) 0.21765(19) 0.4363(3) 0.0401(7) Uani 1 1 d . . . . .
H15 H 0.291710 0.170362 0.403050 0.048 Uiso 1 1 calc R U . . .
C16 C 0.2783(3) 0.2940(3) 0.3777(3) 0.0559(9) Uani 1 1 d . . . . .
H16A H 0.260334 0.341299 0.407434 0.084 Uiso 1 1 calc R U . . .
H16B H 0.221613 0.288539 0.312334 0.084 Uiso 1 1 calc R U . . .
H16C H 0.354692 0.300022 0.376559 0.084 Uiso 1 1 calc R U . . .
C17 C 0.1559(3) 0.2048(3) 0.4398(3) 0.0502(8) Uani 1 1 d . . . . .
H17A H 0.155481 0.154401 0.472548 0.075 Uiso 1 1 calc R U . . .
H17B H 0.097729 0.202724 0.374668 0.075 Uiso 1 1 calc R U . . .
H17C H 0.138936 0.249319 0.474243 0.075 Uiso 1 1 calc R U . . .
C18 C 0.8795(3) 0.3079(2) 0.5947(3) 0.0455(7) Uani 1 1 d . . . . .
C19 C 0.9335(3) 0.3699(3) 0.6756(3) 0.0604(10) Uani 1 1 d . . . . .
H19A H 0.953588 0.418477 0.649364 0.091 Uiso 1 1 calc R U . . .
H19B H 1.002631 0.347145 0.724463 0.091 Uiso 1 1 calc R U . . .
H19C H 0.878463 0.383323 0.704164 0.091 Uiso 1 1 calc R U . . .
C20 C 0.9440(4) 0.3023(3) 0.5261(3) 0.0583(9) Uani 1 1 d . . . . .
H20A H 1.026417 0.293568 0.564302 0.070 Uiso 1 1 calc R U . . .
H20B H 0.915207 0.255145 0.484079 0.070 Uiso 1 1 calc R U . . .
C21 C 0.8758(4) 0.2237(2) 0.6369(4) 0.0598(11) Uani 1 1 d . . . . .
H21A H 0.838120 0.227434 0.682145 0.090 Uiso 1 1 calc R U . . .
H21B H 0.954021 0.203718 0.669921 0.090 Uiso 1 1 calc R U . . .
H21C H 0.833013 0.186828 0.585307 0.090 Uiso 1 1 calc R U . . .
C22 C 0.7261(3) 0.4015(2) 0.4607(3) 0.0517(8) Uani 1 1 d . . . . .
C23 C 0.7477(5) 0.4829(3) 0.5137(4) 0.0685(11) Uani 1 1 d . . . . .
H23A H 0.830278 0.492523 0.544509 0.103 Uiso 1 1 calc R U . . .
H23B H 0.714561 0.481793 0.562187 0.103 Uiso 1 1 calc R U . . .
H23C H 0.712051 0.525933 0.468038 0.103 Uiso 1 1 calc R U . . .
C24 C 0.5964(4) 0.3948(3) 0.3948(4) 0.0702(12) Uani 1 1 d . . . . .
H24A H 0.580540 0.341154 0.366630 0.105 Uiso 1 1 calc R U . . .
H24B H 0.577444 0.434919 0.344013 0.105 Uiso 1 1 calc R U . . .
H24C H 0.550024 0.404134 0.432526 0.105 Uiso 1 1 calc R U . . .
C25 C 0.8011(4) 0.3899(3) 0.4010(3) 0.0645(11) Uani 1 1 d . . . . .
H25A H 0.772334 0.343101 0.358437 0.077 Uiso 1 1 calc R U . . .
H25B H 0.793099 0.437694 0.360343 0.077 Uiso 1 1 calc R U . . .
C26 C 0.9305(4) 0.3769(3) 0.4639(4) 0.0678(11) Uani 1 1 d . . . . .
H26A H 0.974038 0.369896 0.422603 0.081 Uiso 1 1 calc R U . . .
H26B H 0.961270 0.424348 0.504837 0.081 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 2.3776(5) . ?
Ni1 P1 2.0992(9) . ?
Ni1 O1 1.908(2) . ?
Ni1 C1 1.896(3) . ?
P1 O2 1.638(2) . ?
P1 C12 1.840(3) . ?
P1 C15 1.832(4) . ?
O1 N1 1.404(3) . ?
O2 C2 1.405(4) . ?
O3 C9 1.378(4) . ?
O3 C11 1.418(4) . ?
N1 C18 1.546(4) . ?
N1 C22 1.535(4) . ?
C1 C2 1.371(4) . ?
C1 C10 1.433(4) . ?
C2 C3 1.412(4) . ?
C3 C4 1.414(4) . ?
C3 C8 1.422(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.364(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.404(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.373(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.411(4) . ?
C8 C9 1.422(4) . ?
C9 C10 1.368(4) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12 0.9800 . ?
C12 C13 1.520(5) . ?
C12 C14 1.518(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15 0.9800 . ?
C15 C16 1.532(5) . ?
C15 C17 1.522(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.518(6) . ?
C18 C20 1.526(5) . ?
C18 C21 1.523(5) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C26 1.502(7) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.518(6) . ?
C22 C24 1.531(6) . ?
C22 C25 1.530(6) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.529(7) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?

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 91.42(3) . . ?
O1 Ni1 Br1 97.26(7) . . ?
O1 Ni1 P1 171.21(7) . . ?
C1 Ni1 Br1 174.00(9) . . ?
C1 Ni1 P1 82.58(9) . . ?
C1 Ni1 O1 88.74(11) . . ?
O2 P1 Ni1 107.55(8) . . ?
O2 P1 C12 99.90(14) . . ?
O2 P1 C15 102.54(14) . . ?
C12 P1 Ni1 120.66(10) . . ?
C15 P1 Ni1 117.23(12) . . ?
C15 P1 C12 106.08(15) . . ?
N1 O1 Ni1 121.34(18) . . ?
C2 O2 P1 110.04(18) . . ?
C9 O3 C11 116.9(2) . . ?
O1 N1 C18 108.8(2) . . ?
O1 N1 C22 110.5(2) . . ?
C22 N1 C18 118.6(3) . . ?
C2 C1 Ni1 120.7(2) . . ?
C2 C1 C10 116.1(3) . . ?
C10 C1 Ni1 123.1(2) . . ?
O2 C2 C3 117.1(3) . . ?
C1 C2 O2 118.1(3) . . ?
C1 C2 C3 124.7(3) . . ?
C2 C3 C4 123.1(3) . . ?
C2 C3 C8 117.7(3) . . ?
C4 C3 C8 119.2(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 119.9(3) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 119.6 . . ?
C6 C7 C8 120.8(3) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 C3 118.8(3) . . ?
C7 C8 C9 122.9(3) . . ?
C9 C8 C3 118.3(3) . . ?
O3 C9 C8 114.5(3) . . ?
C10 C9 O3 124.0(3) . . ?
C10 C9 C8 121.5(3) . . ?
C1 C10 H10 119.2 . . ?
C9 C10 C1 121.5(3) . . ?
C9 C10 H10 119.2 . . ?
O3 C11 H11A 109.5 . . ?
O3 C11 H11B 109.5 . . ?
O3 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
P1 C12 H12 107.2 . . ?
C13 C12 P1 109.9(2) . . ?
C13 C12 H12 107.2 . . ?
C14 C12 P1 113.6(2) . . ?
C14 C12 H12 107.2 . . ?
C14 C12 C13 111.5(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
P1 C15 H15 107.5 . . ?
C16 C15 P1 110.1(2) . . ?
C16 C15 H15 107.5 . . ?
C17 C15 P1 112.2(3) . . ?
C17 C15 H15 107.5 . . ?
C17 C15 C16 111.6(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 N1 111.6(3) . . ?
C19 C18 C20 112.8(3) . . ?
C19 C18 C21 110.5(3) . . ?
C20 C18 N1 106.8(3) . . ?
C21 C18 N1 105.4(3) . . ?
C21 C18 C20 109.3(3) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 108.8 . . ?
C18 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C26 C20 C18 113.7(4) . . ?
C26 C20 H20A 108.8 . . ?
C26 C20 H20B 108.8 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 N1 111.8(3) . . ?
C23 C22 C24 109.1(4) . . ?
C23 C22 C25 112.7(3) . . ?
C24 C22 N1 105.6(3) . . ?
C25 C22 N1 107.3(3) . . ?
C25 C22 C24 110.1(4) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.0 . . ?
C22 C25 H25B 109.0 . . ?
H25A C25 H25B 107.8 . . ?
C26 C25 C22 113.1(4) . . ?
C26 C25 H25A 109.0 . . ?
C26 C25 H25B 109.0 . . ?
C20 C26 C25 109.3(3) . . ?
C20 C26 H26A 109.8 . . ?
C20 C26 H26B 109.8 . . ?
C25 C26 H26A 109.8 . . ?
C25 C26 H26B 109.8 . . ?
H26A C26 H26B 108.3 . . ?

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 O2 C2 -10.7(2) . . . . ?
Ni1 P1 C12 C13 45.8(3) . . . . ?
Ni1 P1 C12 C14 -79.9(2) . . . . ?
Ni1 P1 C15 C16 -36.1(3) . . . . ?
Ni1 P1 C15 C17 -161.1(2) . . . . ?
Ni1 O1 N1 C18 -125.3(2) . . . . ?
Ni1 O1 N1 C22 102.8(3) . . . . ?
Ni1 C1 C2 O2 -2.2(4) . . . . ?
Ni1 C1 C2 C3 174.8(2) . . . . ?
Ni1 C1 C10 C9 -177.4(2) . . . . ?
P1 Ni1 C1 C2 -3.9(2) . . . . ?
P1 Ni1 C1 C10 174.3(3) . . . . ?
P1 O2 C2 C1 8.8(3) . . . . ?
P1 O2 C2 C3 -168.4(2) . . . . ?
O1 Ni1 C1 C2 174.7(3) . . . . ?
O1 Ni1 C1 C10 -7.1(3) . . . . ?
O1 N1 C18 C19 -54.3(4) . . . . ?
O1 N1 C18 C20 -178.0(3) . . . . ?
O1 N1 C18 C21 65.8(4) . . . . ?
O1 N1 C22 C23 53.1(4) . . . . ?
O1 N1 C22 C24 -65.4(4) . . . . ?
O1 N1 C22 C25 177.2(3) . . . . ?
O2 P1 C12 C13 -71.6(3) . . . . ?
O2 P1 C12 C14 162.8(2) . . . . ?
O2 P1 C15 C16 81.4(3) . . . . ?
O2 P1 C15 C17 -43.6(3) . . . . ?
O2 C2 C3 C4 1.9(5) . . . . ?
O2 C2 C3 C8 -179.4(3) . . . . ?
O3 C9 C10 C1 179.7(3) . . . . ?
N1 C18 C20 C26 53.8(5) . . . . ?
N1 C22 C25 C26 -52.8(5) . . . . ?
C1 C2 C3 C4 -175.1(3) . . . . ?
C1 C2 C3 C8 3.6(5) . . . . ?
C2 C1 C10 C9 0.9(4) . . . . ?
C2 C3 C4 C5 177.8(3) . . . . ?
C2 C3 C8 C7 -178.9(3) . . . . ?
C2 C3 C8 C9 -0.9(4) . . . . ?
C3 C4 C5 C6 0.9(6) . . . . ?
C3 C8 C9 O3 -179.9(3) . . . . ?
C3 C8 C9 C10 -1.5(4) . . . . ?
C4 C3 C8 C7 -0.1(4) . . . . ?
C4 C3 C8 C9 177.9(3) . . . . ?
C4 C5 C6 C7 0.0(6) . . . . ?
C5 C6 C7 C8 -1.1(5) . . . . ?
C6 C7 C8 C3 1.1(5) . . . . ?
C6 C7 C8 C9 -176.8(3) . . . . ?
C7 C8 C9 O3 -1.9(4) . . . . ?
C7 C8 C9 C10 176.4(3) . . . . ?
C8 C3 C4 C5 -0.9(5) . . . . ?
C8 C9 C10 C1 1.5(5) . . . . ?
C10 C1 C2 O2 179.5(3) . . . . ?
C10 C1 C2 C3 -3.6(5) . . . . ?
C11 O3 C9 C8 -171.1(3) . . . . ?
C11 O3 C9 C10 10.6(4) . . . . ?
C12 P1 O2 C2 116.0(2) . . . . ?
C12 P1 C15 C16 -174.2(2) . . . . ?
C12 P1 C15 C17 60.7(3) . . . . ?
C15 P1 O2 C2 -134.9(2) . . . . ?
C15 P1 C12 C13 -177.8(3) . . . . ?
C15 P1 C12 C14 56.6(3) . . . . ?
C18 N1 C22 C23 -73.5(4) . . . . ?
C18 N1 C22 C24 168.0(3) . . . . ?
C18 N1 C22 C25 50.6(4) . . . . ?
C18 C20 C26 C25 -60.2(5) . . . . ?
C19 C18 C20 C26 -69.2(5) . . . . ?
C21 C18 C20 C26 167.4(4) . . . . ?
C22 N1 C18 C19 73.1(4) . . . . ?
C22 N1 C18 C20 -50.6(4) . . . . ?
C22 N1 C18 C21 -166.8(3) . . . . ?
C22 C25 C26 C20 59.5(5) . . . . ?
C23 C22 C25 C26 70.7(5) . . . . ?
C24 C22 C25 C26 -167.3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_vrf_PLAT971_rajib741            
;
RESPONSE
Atom misassignment is chemically not possible and there is no 
indication of disorder in the respective atom. This and several 
other maxima less than 1 e-/Ang^3 away from heavy atoms
might be caused by fourier truncation errors.
;
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
####################################################################### 
# 
# 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_rajib891
_database_code_depnum_ccdc_archive 'CCDC 2287049'
loop_
_audit_author_name
_audit_author_address
'Rajib Kumar Sarker'
;University of Montreal
Canada
;
_audit_update_record             
;
2023-08-06 deposited with the CCDC.	2024-05-24 downloaded from the CCDC.
;
_audit_creation_date             2023-08-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H27 Br0.239 Cl0.761 N Ni O2 P'
_chemical_formula_sum            'C16 H27 Br0.24 Cl0.76 N Ni O2 P'
_chemical_formula_weight         401.18
_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 0.0137 0.0067 '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 -0.9502 1.0410 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -1.3357 3.2904 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2543 0.3332 '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                   7.7771(3)
_cell_length_b                   24.7633(8)
_cell_length_c                   9.4301(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.0120(10)
_cell_angle_gamma                90
_cell_volume                     1802.53(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9882
_cell_measurement_temperature    150
_cell_measurement_theta_max      54.885
_cell_measurement_theta_min      3.106
_shelx_estimated_absorpt_T_max   0.572
_shelx_estimated_absorpt_T_min   0.362
_exptl_absorpt_coefficient_mu    7.580
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0955 before and 0.0467 after correction.
The Ratio of minimum to maximum transmission is 0.7488.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             841
_exptl_crystal_size_max          0.168
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.083
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon III CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15394
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.870
_diffrn_reflns_theta_min         3.105
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            'Bruker CMOS Photon III '
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_current           2.86
_diffrn_source_power             0.19937059999999998
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_source_voltage           69.71
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3236
_reflns_number_total             3317
_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 (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0275
_refine_ls_restrained_S_all      1.136
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0264P)²+1.2483P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0697
_refine_ls_wR_factor_ref         0.0700
_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. Uiso/Uaniso restraints and constraints
Uanis(Br1) = Uanis(Cl1)
3. Others
 Sof(Cl1)=1-FVAR(1)
 Sof(Br1)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10)
4.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6)
4.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_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 0.2452(16) 0.5606(5) 0.5351(15) 0.0298(6) Uani 0.239(2) 1 d . . P A 1
Ni1 Ni 0.40559(3) 0.63084(2) 0.43970(3) 0.01912(10) Uani 1 1 d . . . . .
Cl1 Cl 0.2628(11) 0.5658(4) 0.5366(10) 0.0298(6) Uani 0.761(2) 1 d . . P A 2
P1 P 0.26411(6) 0.61781(2) 0.23802(5) 0.01762(12) Uani 1 1 d . . . . .
O1 O 0.35537(17) 0.65633(5) 0.12532(13) 0.0222(3) Uani 1 1 d . . . . .
O2 O 0.7871(2) 0.59424(6) 0.86287(15) 0.0337(3) Uani 1 1 d . . . . .
N1 N 0.5901(2) 0.63440(7) 0.60564(18) 0.0227(3) Uani 1 1 d . . . . .
H1 H 0.658(3) 0.6589(10) 0.591(3) 0.029(6) Uiso 1 1 d . . . . .
C1 C 0.4562(2) 0.69648(7) 0.19847(19) 0.0195(4) Uani 1 1 d . . . . .
C2 C 0.4902(2) 0.69208(7) 0.34692(19) 0.0199(4) Uani 1 1 d . . . . .
C3 C 0.5783(2) 0.73648(7) 0.4140(2) 0.0224(4) Uani 1 1 d . . . . .
H3 H 0.600921 0.736802 0.513120 0.027 Uiso 1 1 calc R U . . .
C4 C 0.6332(2) 0.78014(7) 0.3374(2) 0.0243(4) Uani 1 1 d . . . . .
H4 H 0.690920 0.808864 0.385741 0.029 Uiso 1 1 calc R U . . .
C5 C 0.6020(2) 0.78077(7) 0.1897(2) 0.0236(4) Uani 1 1 d . . . . .
H5 H 0.641834 0.809273 0.138380 0.028 Uiso 1 1 calc R U . . .
C6 C 0.5108(2) 0.73850(7) 0.1187(2) 0.0222(4) Uani 1 1 d . . . . .
H6 H 0.487054 0.738505 0.019576 0.027 Uiso 1 1 calc R U . . .
C7 C 0.2824(2) 0.55113(7) 0.1608(2) 0.0220(4) Uani 1 1 d . . . . .
H7 H 0.217942 0.526004 0.214780 0.026 Uiso 1 1 calc R U . . .
C8 C 0.4716(3) 0.53294(9) 0.1798(2) 0.0304(4) Uani 1 1 d . . . . .
H8A H 0.537596 0.555859 0.124598 0.046 Uiso 1 1 calc R U . . .
H8B H 0.478659 0.496299 0.147761 0.046 Uiso 1 1 calc R U . . .
H8C H 0.517267 0.535242 0.278847 0.046 Uiso 1 1 calc R U . . .
C9 C 0.2034(3) 0.54806(9) 0.0044(2) 0.0299(4) Uani 1 1 d . . . . .
H9A H 0.083706 0.558511 -0.003494 0.045 Uiso 1 1 calc R U . . .
H9B H 0.211988 0.511747 -0.029694 0.045 Uiso 1 1 calc R U . . .
H9C H 0.264733 0.571982 -0.051814 0.045 Uiso 1 1 calc R U . . .
C10 C 0.0363(2) 0.63764(8) 0.2013(2) 0.0247(4) Uani 1 1 d . . . . .
H10 H 0.009251 0.642636 0.097908 0.030 Uiso 1 1 calc R U . . .
C11 C 0.0113(3) 0.69158(10) 0.2729(3) 0.0387(5) Uani 1 1 d . . . . .
H11A H 0.023948 0.686820 0.374721 0.058 Uiso 1 1 calc R U . . .
H11B H -0.102390 0.705224 0.241145 0.058 Uiso 1 1 calc R U . . .
H11C H 0.096669 0.716770 0.248224 0.058 Uiso 1 1 calc R U . . .
C12 C -0.0869(3) 0.59526(10) 0.2478(3) 0.0388(5) Uani 1 1 d . . . . .
H12A H -0.084603 0.563843 0.188482 0.058 Uiso 1 1 calc R U . . .
H12B H -0.202365 0.609669 0.238781 0.058 Uiso 1 1 calc R U . . .
H12C H -0.051631 0.585549 0.345615 0.058 Uiso 1 1 calc R U . . .
C13 C 0.6980(3) 0.58485(8) 0.6086(2) 0.0267(4) Uani 1 1 d . . . . .
H13A H 0.742653 0.580754 0.517532 0.032 Uiso 1 1 calc R U . . .
H13B H 0.626984 0.553578 0.622717 0.032 Uiso 1 1 calc R U . . .
C14 C 0.8476(3) 0.58745(9) 0.7270(2) 0.0292(4) Uani 1 1 d . . . . .
H14A H 0.914838 0.554453 0.727406 0.035 Uiso 1 1 calc R U . . .
H14B H 0.922668 0.617402 0.709686 0.035 Uiso 1 1 calc R U . . .
C15 C 0.6910(3) 0.64310(10) 0.8649(2) 0.0338(5) Uani 1 1 d . . . . .
H15A H 0.766038 0.673434 0.850932 0.041 Uiso 1 1 calc R U . . .
H15B H 0.650370 0.647217 0.957535 0.041 Uiso 1 1 calc R U . . .
C16 C 0.5375(3) 0.64365(9) 0.7497(2) 0.0266(4) Uani 1 1 d . . . . .
H16A H 0.456168 0.615816 0.769848 0.032 Uiso 1 1 calc R U . . .
H16B H 0.479101 0.678232 0.750900 0.032 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 2.380(11) . ?
Ni1 Cl1 2.216(8) . ?
Ni1 P1 2.1026(5) . ?
Ni1 N1 1.9921(17) . ?
Ni1 C2 1.9076(18) . ?
P1 O1 1.6514(13) . ?
P1 C7 1.8172(18) . ?
P1 C10 1.830(2) . ?
O1 C1 1.395(2) . ?
O2 C14 1.427(3) . ?
O2 C15 1.424(3) . ?
N1 H1 0.83(3) . ?
N1 C13 1.485(3) . ?
N1 C16 1.484(3) . ?
C1 C2 1.397(3) . ?
C1 C6 1.381(3) . ?
C2 C3 1.405(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.395(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.390(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9800 . ?
C7 C8 1.528(3) . ?
C7 C9 1.529(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10 0.9800 . ?
C10 C11 1.520(3) . ?
C10 C12 1.522(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.512(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.513(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?

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 89.4(3) . . ?
P1 Ni1 Cl1 91.6(2) . . ?
N1 Ni1 Br1 95.5(3) . . ?
N1 Ni1 Cl1 93.3(2) . . ?
N1 Ni1 P1 164.72(5) . . ?
C2 Ni1 Br1 168.6(3) . . ?
C2 Ni1 Cl1 170.2(3) . . ?
C2 Ni1 P1 83.04(6) . . ?
C2 Ni1 N1 93.98(7) . . ?
O1 P1 Ni1 105.96(5) . . ?
O1 P1 C7 101.89(8) . . ?
O1 P1 C10 101.85(8) . . ?
C7 P1 Ni1 116.36(7) . . ?
C7 P1 C10 106.83(9) . . ?
C10 P1 Ni1 121.16(7) . . ?
C1 O1 P1 110.68(11) . . ?
C15 O2 C14 110.06(16) . . ?
Ni1 N1 H1 108.5(17) . . ?
C13 N1 Ni1 109.24(12) . . ?
C13 N1 H1 103.9(17) . . ?
C16 N1 Ni1 118.24(13) . . ?
C16 N1 H1 106.8(17) . . ?
C16 N1 C13 109.20(15) . . ?
O1 C1 C2 117.77(16) . . ?
C6 C1 O1 117.33(16) . . ?
C6 C1 C2 124.88(17) . . ?
C1 C2 Ni1 119.21(13) . . ?
C1 C2 C3 114.35(16) . . ?
C3 C2 Ni1 126.34(14) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 C2 122.47(17) . . ?
C4 C3 H3 118.8 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.13(17) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.53(17) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 118.52(17) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
P1 C7 H7 107.4 . . ?
C8 C7 P1 110.02(13) . . ?
C8 C7 H7 107.4 . . ?
C8 C7 C9 111.50(16) . . ?
C9 C7 P1 112.94(13) . . ?
C9 C7 H7 107.4 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
P1 C10 H10 107.9 . . ?
C11 C10 P1 108.97(14) . . ?
C11 C10 H10 107.9 . . ?
C11 C10 C12 111.01(18) . . ?
C12 C10 P1 112.94(15) . . ?
C12 C10 H10 107.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 H13A 109.4 . . ?
N1 C13 H13B 109.4 . . ?
N1 C13 C14 111.14(17) . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
O2 C14 C13 111.09(16) . . ?
O2 C14 H14A 109.4 . . ?
O2 C14 H14B 109.4 . . ?
C13 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
O2 C15 H15A 109.3 . . ?
O2 C15 H15B 109.3 . . ?
O2 C15 C16 111.58(18) . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
N1 C16 C15 111.98(17) . . ?
N1 C16 H16A 109.2 . . ?
N1 C16 H16B 109.2 . . ?
C15 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?

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 -18.31(12) . . . . ?
Ni1 P1 C7 C8 -44.28(15) . . . . ?
Ni1 P1 C7 C9 -169.58(12) . . . . ?
Ni1 P1 C10 C11 39.56(17) . . . . ?
Ni1 P1 C10 C12 -84.31(16) . . . . ?
Ni1 N1 C13 C14 176.12(13) . . . . ?
Ni1 N1 C16 C15 177.71(14) . . . . ?
Ni1 C2 C3 C4 -178.90(14) . . . . ?
P1 O1 C1 C2 11.6(2) . . . . ?
P1 O1 C1 C6 -166.63(13) . . . . ?
O1 P1 C7 C8 70.42(14) . . . . ?
O1 P1 C7 C9 -54.88(15) . . . . ?
O1 P1 C10 C11 -77.52(16) . . . . ?
O1 P1 C10 C12 158.62(15) . . . . ?
O1 C1 C2 Ni1 2.4(2) . . . . ?
O1 C1 C2 C3 -174.30(15) . . . . ?
O1 C1 C6 C5 175.98(16) . . . . ?
O2 C15 C16 N1 -55.8(2) . . . . ?
N1 C13 C14 O2 58.3(2) . . . . ?
C1 C2 C3 C4 -2.5(3) . . . . ?
C2 C1 C6 C5 -2.1(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 2.1(3) . . . . ?
C4 C5 C6 C1 -1.0(3) . . . . ?
C6 C1 C2 Ni1 -179.61(14) . . . . ?
C6 C1 C2 C3 3.7(3) . . . . ?
C7 P1 O1 C1 -140.46(12) . . . . ?
C7 P1 C10 C11 176.02(15) . . . . ?
C7 P1 C10 C12 52.15(17) . . . . ?
C10 P1 O1 C1 109.27(13) . . . . ?
C10 P1 C7 C8 176.86(14) . . . . ?
C10 P1 C7 C9 51.56(16) . . . . ?
C13 N1 C16 C15 52.0(2) . . . . ?
C14 O2 C15 C16 58.8(2) . . . . ?
C15 O2 C14 C13 -60.2(2) . . . . ?
C16 N1 C13 C14 -53.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_vrf_PLAT077_rajib891            
;
RESPONSE
There were substitution bet Cl and Br. Their occupation factors add up to 1.
;
_vrf_PLAT171_rajib891            
;
RESPONSE
Br refined with unexpectedly high thermal motion. NMR indicates the 
presence of Cl contain and Br, Cl disorder was refined with 
appropriate restraints/constraints. 
;
_vrf_PLAT420_rajib891            
;
RESPONSE
H atom is attached to a coordinated N atom of a 
morpholine moiety. No other geometry is possible.
;
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
####################################################################### 
# 
# 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_rajib1021
_database_code_depnum_ccdc_archive 'CCDC 2309506'
loop_
_audit_author_name
_audit_author_address
'Rajib Kumar Sarker'
;University of Montreal
Canada
;
_audit_update_record             
;
2023-11-21 deposited with the CCDC.	2024-05-24 downloaded from the CCDC.
;
_audit_creation_date             2023-11-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 F3 O2, C9 H20 N'
_chemical_formula_sum            'C11 H20 F3 N O2'
_chemical_formula_weight         255.28
_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 0.0137 0.0067 '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 0.0599 0.0411 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   19.9649(14)
_cell_length_b                   8.3817(6)
_cell_length_c                   15.8150(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.234(4)
_cell_angle_gamma                90
_cell_volume                     2645.9(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9905
_cell_measurement_temperature    150
_cell_measurement_theta_max      65.394
_cell_measurement_theta_min      3.854
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.858
_exptl_absorpt_coefficient_mu    0.632
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_correction_T_min  0.6242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1376 before and 0.0716 after correction.
The Ratio of minimum to maximum transmission is 0.8293.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.099
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon III CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            29827
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         65.908
_diffrn_reflns_theta_min         3.853
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            'Bruker CMOS Photon III '
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_current           2.86
_diffrn_source_power             0.19937059999999998
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_source_voltage           69.71
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2828
_reflns_number_total             3447
_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 (2019) V8.40A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2019) V8.40A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3447
_refine_ls_number_restraints     267
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0566
_refine_ls_restrained_S_all      1.137
_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)+(0.0891P)²+1.6580P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1590
_refine_ls_wR_factor_ref         0.1699
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F2-C11B \\sim F5-C11B \\sim F3-C11B \\sim F4-C11B \\sim F1-C11B \\sim F6-C11B
 with sigma of 0.02
 F1-F2 \\sim F2-F3 \\sim F3-F1 \\sim F4-F5 \\sim F5-F6 \\sim F6-F4
 with sigma of 0.02
 O1B-C10 \\sim O1A-C10
 with sigma of 0.01
 C11B-C10 \\sim C11A-C10
 with sigma of 0.01
 C11A-C10 \\sim C11B-C10
 with sigma of 0.01
 O2A-C10 \\sim O2B-C10
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1A with sigma of 0.01 and sigma
for terminal atoms of 0.01 within 1A
F1 \\sim F2 \\sim F3 \\sim F4 \\sim F5 \\sim F6 \\sim O1B \\sim O1A \\sim O2A
\\sim O2B \\sim C10 \\sim C11A \\sim C11B: within 1.7A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 1.7A
4. Rigid body (RIGU) restrains
 F1, F2, F3, F4, F5, F6, O1B, O1A, O2A, O2B, C10, C11A, C11B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(F4)=Sof(F5)=Sof(F6)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
 Sof(O1A)=Sof(O2B)=Sof(C11B)=1-FVAR(2)
 Sof(O1B)=Sof(O2A)=Sof(C11A)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
6.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.5269(3) 0.6340(7) 0.5834(4) 0.105(2) Uani 0.584(6) 1 d D U P A 1
F2 F 0.56264(15) 0.4079(3) 0.6212(4) 0.0938(14) Uani 0.584(6) 1 d D U P A 1
F3 F 0.56867(17) 0.5952(8) 0.70662(19) 0.1055(17) Uani 0.584(6) 1 d D U P A 1
F4 F 0.5564(2) 0.7203(9) 0.6721(4) 0.112(2) Uani 0.416(6) 1 d D U P A 2
F5 F 0.5626(2) 0.4697(9) 0.6733(5) 0.102(2) Uani 0.416(6) 1 d D U P A 2
F6 F 0.5319(4) 0.5927(10) 0.5632(5) 0.087(2) Uani 0.416(6) 1 d D U P A 2
O1B O 0.6876(3) 0.5153(10) 0.6347(6) 0.0503(14) Uani 0.60(3) 1 d D U P B 1
O1A O 0.6901(5) 0.5052(11) 0.6109(10) 0.0481(18) Uani 0.40(3) 1 d D U P B 2
O2A O 0.6489(5) 0.7344(7) 0.5597(5) 0.0573(13) Uani 0.60(3) 1 d D U P B 1
O2B O 0.6613(6) 0.6987(18) 0.5417(8) 0.061(2) Uani 0.40(3) 1 d D U P B 2
C10 C 0.64689(8) 0.60464(17) 0.59753(9) 0.0384(3) Uani 1 1 d D U . . .
C11A C 0.5750(3) 0.5587(14) 0.6241(6) 0.0520(15) Uani 0.60(3) 1 d D U P A 1
C11B C 0.5739(3) 0.5946(13) 0.6282(6) 0.0465(19) Uani 0.40(3) 1 d D U P A 2
H1A H 0.8229(9) 0.654(2) 0.5463(12) 0.040(4) Uiso 1 1 d . . . . .
N1 N 0.82050(5) 0.59588(12) 0.59153(7) 0.0260(2) Uani 1 1 d . . . . .
H1B H 0.7740(11) 0.581(2) 0.5999(12) 0.050(5) Uiso 1 1 d . . . . .
C1 C 0.84764(7) 0.69690(15) 0.66433(8) 0.0318(3) Uani 1 1 d . . . . .
C2 C 0.81133(9) 0.85664(18) 0.65548(13) 0.0515(4) Uani 1 1 d . . . . .
H2A H 0.821937 0.905171 0.601004 0.077 Uiso 1 1 calc R U . . .
H2B H 0.825891 0.927854 0.701461 0.077 Uiso 1 1 calc R U . . .
H2C H 0.762885 0.839390 0.658300 0.077 Uiso 1 1 calc R U . . .
C3 C 0.83118(10) 0.6239(2) 0.74969(10) 0.0501(4) Uani 1 1 d . . . . .
H3A H 0.783937 0.592140 0.749580 0.075 Uiso 1 1 calc R U . . .
H3B H 0.839550 0.702642 0.794488 0.075 Uiso 1 1 calc R U . . .
H3C H 0.859467 0.530007 0.759865 0.075 Uiso 1 1 calc R U . . .
C4 C 0.92289(7) 0.71626(18) 0.65291(9) 0.0395(3) Uani 1 1 d . . . . .
H4A H 0.930518 0.786845 0.603859 0.047 Uiso 1 1 calc R U . . .
H4B H 0.942516 0.768862 0.703722 0.047 Uiso 1 1 calc R U . . .
C5 C 0.95875(7) 0.5588(2) 0.63901(11) 0.0471(4) Uani 1 1 d . . . . .
H5A H 0.954015 0.489991 0.689408 0.057 Uiso 1 1 calc R U . . .
H5B H 1.007072 0.578651 0.630959 0.057 Uiso 1 1 calc R U . . .
C6 C 0.92914(7) 0.47442(19) 0.56134(10) 0.0421(3) Uani 1 1 d . . . . .
H6A H 0.953140 0.372405 0.553180 0.051 Uiso 1 1 calc R U . . .
H6B H 0.936437 0.541488 0.510838 0.051 Uiso 1 1 calc R U . . .
C7 C 0.85435(7) 0.44043(14) 0.56826(8) 0.0307(3) Uani 1 1 d . . . . .
C8 C 0.83916(10) 0.31004(17) 0.63201(11) 0.0488(4) Uani 1 1 d . . . . .
H8A H 0.863420 0.331915 0.685280 0.073 Uiso 1 1 calc R U . . .
H8B H 0.853377 0.206638 0.609703 0.073 Uiso 1 1 calc R U . . .
H8C H 0.790914 0.307601 0.642085 0.073 Uiso 1 1 calc R U . . .
C9 C 0.82408(9) 0.39528(19) 0.48174(10) 0.0446(4) Uani 1 1 d . . . . .
H9A H 0.775616 0.380486 0.486540 0.067 Uiso 1 1 calc R U . . .
H9B H 0.844419 0.295828 0.462222 0.067 Uiso 1 1 calc R U . . .
H9C H 0.832823 0.480622 0.441085 0.067 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
F1 C11A 1.306(9) . ?
F2 C11A 1.288(12) . ?
F3 C11A 1.349(10) . ?
F4 C11B 1.312(10) . ?
F5 C11B 1.289(10) . ?
F6 C11B 1.313(11) . ?
O1B C10 1.244(4) . ?
O1A C10 1.215(6) . ?
O2A C10 1.243(4) . ?
O2B C10 1.223(5) . ?
C10 C11A 1.553(5) . ?
C10 C11B 1.548(6) . ?
N1 H1A 0.866(19) . ?
N1 H1B 0.95(2) . ?
N1 C1 1.5197(16) . ?
N1 C7 1.5167(15) . ?
C1 C2 1.528(2) . ?
C1 C3 1.524(2) . ?
C1 C4 1.5258(19) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.520(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.526(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.526(2) . ?
C7 C8 1.5218(19) . ?
C7 C9 1.532(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 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
O1B C10 C11A 108.8(6) . . ?
O1A C10 O2B 113.0(12) . . ?
O1A C10 C11B 125.3(8) . . ?
O2A C10 O1B 136.6(6) . . ?
O2A C10 C11A 112.7(5) . . ?
O2B C10 C11B 120.0(7) . . ?
F1 C11A F3 106.5(8) . . ?
F1 C11A C10 114.9(7) . . ?
F2 C11A F1 108.6(7) . . ?
F2 C11A F3 103.5(6) . . ?
F2 C11A C10 114.3(7) . . ?
F3 C11A C10 108.1(6) . . ?
F4 C11B F6 104.5(8) . . ?
F4 C11B C10 112.6(7) . . ?
F5 C11B F4 107.9(7) . . ?
F5 C11B F6 107.9(8) . . ?
F5 C11B C10 113.2(7) . . ?
F6 C11B C10 110.2(7) . . ?
H1A N1 H1B 105.2(16) . . ?
C1 N1 H1A 106.8(12) . . ?
C1 N1 H1B 107.6(12) . . ?
C7 N1 H1A 104.3(12) . . ?
C7 N1 H1B 111.2(12) . . ?
C7 N1 C1 120.59(10) . . ?
N1 C1 C2 104.97(11) . . ?
N1 C1 C3 111.54(11) . . ?
N1 C1 C4 107.79(10) . . ?
C3 C1 C2 108.79(13) . . ?
C3 C1 C4 112.28(13) . . ?
C4 C1 C2 111.25(12) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.0 . . ?
C1 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 C1 113.13(12) . . ?
C5 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C4 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
C4 C5 C6 110.09(12) . . ?
H5A C5 H5B 108.2 . . ?
C6 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
C5 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C5 C6 C7 113.04(12) . . ?
H6A C6 H6B 107.8 . . ?
C7 C6 H6A 109.0 . . ?
C7 C6 H6B 109.0 . . ?
N1 C7 C6 107.39(10) . . ?
N1 C7 C8 111.10(11) . . ?
N1 C7 C9 105.05(11) . . ?
C6 C7 C9 110.48(12) . . ?
C8 C7 C6 113.00(12) . . ?
C8 C7 C9 109.51(12) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1B O1A 0.95(2) 1.80(2) 2.735(11) 166.9(18) . yes

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
O1B C10 C11A F1 -173.9(11) . . . . ?
O1B C10 C11A F2 -47.4(9) . . . . ?
O1B C10 C11A F3 67.3(7) . . . . ?
O1A C10 C11B F4 125.0(10) . . . . ?
O1A C10 C11B F5 2.2(13) . . . . ?
O1A C10 C11B F6 -118.7(12) . . . . ?
O2A C10 C11A F1 18.8(9) . . . . ?
O2A C10 C11A F2 145.3(7) . . . . ?
O2A C10 C11A F3 -99.9(9) . . . . ?
O2B C10 C11B F4 -71.2(13) . . . . ?
O2B C10 C11B F5 166.0(12) . . . . ?
O2B C10 C11B F6 45.1(11) . . . . ?
N1 C1 C4 C5 -50.91(15) . . . . ?
C1 N1 C7 C6 -49.36(14) . . . . ?
C1 N1 C7 C8 74.69(15) . . . . ?
C1 N1 C7 C9 -166.99(11) . . . . ?
C1 C4 C5 C6 58.25(17) . . . . ?
C2 C1 C4 C5 -165.47(13) . . . . ?
C3 C1 C4 C5 72.34(16) . . . . ?
C4 C5 C6 C7 -58.83(18) . . . . ?
C5 C6 C7 N1 51.76(16) . . . . ?
C5 C6 C7 C8 -71.12(16) . . . . ?
C5 C6 C7 C9 165.80(13) . . . . ?
C7 N1 C1 C2 167.65(11) . . . . ?
C7 N1 C1 C3 -74.71(15) . . . . ?
C7 N1 C1 C4 48.98(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_vrf_PLAT242_rajib1021           
;
RESPONSE
Atom misassignment not possible for chemical reasons. The increased thermal 
parameter might indicate a slight disorder of this group.
;
_vrf_PLAT250_rajib1021           
;
RESPONSE
Orientation of thermal ellipsoids agrees with thermal motion. No common 
deformation in one direction is noticeable.
;
####################################################################### 
# 
# 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_rajib901
_database_code_depnum_ccdc_archive 'CCDC 2287047'
loop_
_audit_author_name
_audit_author_address
'Rajib Kumar Sarker'
;University of Montreal
Canada
;
_audit_update_record             
;
2023-08-06 deposited with the CCDC.	2024-05-24 downloaded from the CCDC.
;
_audit_creation_date             2023-08-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H39 Br0.25 Cl0.75 N Ni O3 P'
_chemical_formula_sum            'C22 H39 Br0.25 Cl0.75 N Ni O3 P'
_chemical_formula_weight         501.78
_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 0.0137 0.0067 '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 -0.9338 1.0006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -1.3357 3.2904 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2543 0.3332 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.9270(5)
_cell_length_b                   14.1466(6)
_cell_length_c                   29.5812(12)
_cell_angle_alpha                90
_cell_angle_beta                 98.950(2)
_cell_angle_gamma                90
_cell_volume                     4930.4(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9875
_cell_measurement_temperature    150
_cell_measurement_theta_max      54.862
_cell_measurement_theta_min      2.632
_shelx_estimated_absorpt_T_max   0.557
_shelx_estimated_absorpt_T_min   0.434
_exptl_absorpt_coefficient_mu    5.623
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0986 before and 0.0568 after correction.
The Ratio of minimum to maximum transmission is 0.7702.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2132
_exptl_crystal_size_max          0.178
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.118
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon III CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            45605
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.923
_diffrn_reflns_theta_min         2.631
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            'Bruker CMOS Photon III '
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_current           2.86
_diffrn_source_power             0.19937059999999998
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_source_voltage           69.71
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8631
_reflns_number_total             9244
_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 (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.669
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     555
_refine_ls_number_reflns         9244
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0284
_refine_ls_restrained_S_all      1.028
_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)+(0.0366P)²+2.3477P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0721
_refine_ls_wR_factor_ref         0.0734
_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. Restrained distances
 Cl2-Ni2 \\sim Cl1-Ni1
 with sigma of 0.02
 Br2-Ni2 \\sim Br1-Ni1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Br1 \\sim Cl1 \\sim Br2 \\sim Cl2: within 1A with sigma of 0.01 and sigma for
terminal atoms of 0.01 within 1A
Uanis(Cl2) = Uanis(Br2)
Uanis(Br1) = Uanis(Cl1)
4. Others
 Fixed Sof: Br1(0.25) Cl1(0.75) Br2(0.25) Cl2(0.75)
5.a Ternary CH refined with riding coordinates:
 C8(H8), C11(H11), C30(H30), C33(H33)
5.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C39(H39A,H39B), C40(H40A,
 H40B), C41(H41A,H41B)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C25(H25), C26(H26), C28(H28)
5.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C),
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C21(H21A,H21B,
 H21C), C22(H22A,H22B,H22C), C29(H29A,H29B,H29C), C31(H31A,H31B,H31C), C32(H32A,
 H32B,H32C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C37(H37A,H37B,H37C),
 C38(H38A,H38B,H38C), C43(H43A,H43B,H43C), C44(H44A,H44B,H44C)
;
_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 0.0502(6) 0.8503(6) 0.43380(17) 0.0361(4) Uani 0.25 1 d D U P A 2
Ni1 Ni 0.15344(2) 0.74543(2) 0.48754(2) 0.02962(7) Uani 1 1 d D . . . .
Cl1 Cl 0.0444(4) 0.8499(4) 0.44306(12) 0.0361(4) Uani 0.75 1 d D U P A 1
P1 P 0.28760(4) 0.75894(3) 0.45022(2) 0.02922(10) Uani 1 1 d . . . . .
O1 O 0.39626(10) 0.69939(9) 0.47714(4) 0.0341(3) Uani 1 1 d . . . . .
O2 O 0.04261(11) 0.71651(11) 0.52571(5) 0.0443(3) Uani 1 1 d . . . . .
O3 O 0.49288(13) 0.47746(11) 0.59625(5) 0.0505(4) Uani 1 1 d . . . . .
N1 N -0.06944(12) 0.74438(10) 0.51242(5) 0.0287(3) Uani 1 1 d . . . . .
H1 H -0.0672(17) 0.7887(15) 0.4874(7) 0.036(5) Uiso 1 1 d . . . . .
C1 C 0.36614(15) 0.64977(13) 0.51412(6) 0.0291(4) Uani 1 1 d . . . . .
C2 C 0.25766(15) 0.66632(13) 0.52510(6) 0.0299(4) Uani 1 1 d . . . . .
C3 C 0.23404(16) 0.61881(14) 0.56360(6) 0.0363(4) Uani 1 1 d . . . . .
H3 H 0.164061 0.628638 0.572980 0.044 Uiso 1 1 calc R U . . .
C4 C 0.31061(17) 0.55707(14) 0.58879(6) 0.0374(4) Uani 1 1 d . . . . .
H4 H 0.292242 0.527610 0.614773 0.045 Uiso 1 1 calc R U . . .
C5 C 0.41395(16) 0.53998(13) 0.57488(6) 0.0352(4) Uani 1 1 d . . . . .
C6 C 0.44313(16) 0.58757(13) 0.53717(6) 0.0346(4) Uani 1 1 d . . . . .
H6 H 0.513082 0.577483 0.527816 0.042 Uiso 1 1 calc R U . . .
C7 C 0.4623(3) 0.4266(2) 0.63428(8) 0.0703(8) Uani 1 1 d . . . . .
H7A H 0.393884 0.391538 0.624555 0.105 Uiso 1 1 calc R U . . .
H7B H 0.450153 0.470326 0.657860 0.105 Uiso 1 1 calc R U . . .
H7C H 0.522319 0.383795 0.645956 0.105 Uiso 1 1 calc R U . . .
C8 C 0.27586(19) 0.70395(15) 0.39367(6) 0.0432(5) Uani 1 1 d . . . . .
H8 H 0.352657 0.701210 0.385829 0.052 Uiso 1 1 calc R U . . .
C9 C 0.2354(2) 0.60194(15) 0.39672(8) 0.0485(5) Uani 1 1 d . . . . .
H9A H 0.282201 0.570331 0.421501 0.073 Uiso 1 1 calc R U . . .
H9B H 0.240588 0.569734 0.368555 0.073 Uiso 1 1 calc R U . . .
H9C H 0.158009 0.601699 0.402015 0.073 Uiso 1 1 calc R U . . .
C10 C 0.2034(3) 0.75838(18) 0.35580(8) 0.0677(8) Uani 1 1 d . . . . .
H10A H 0.126459 0.760400 0.361642 0.101 Uiso 1 1 calc R U . . .
H10B H 0.205703 0.727625 0.327031 0.101 Uiso 1 1 calc R U . . .
H10C H 0.232018 0.821628 0.354715 0.101 Uiso 1 1 calc R U . . .
C11 C 0.34629(16) 0.87653(13) 0.44487(6) 0.0338(4) Uani 1 1 d . . . . .
H11 H 0.290334 0.912811 0.424045 0.041 Uiso 1 1 calc R U . . .
C12 C 0.35970(19) 0.92488(15) 0.49163(7) 0.0459(5) Uani 1 1 d . . . . .
H12A H 0.287896 0.925584 0.502459 0.069 Uiso 1 1 calc R U . . .
H12B H 0.385559 0.988582 0.488892 0.069 Uiso 1 1 calc R U . . .
H12C H 0.414079 0.890819 0.512899 0.069 Uiso 1 1 calc R U . . .
C13 C 0.45662(18) 0.87727(16) 0.42506(7) 0.0435(5) Uani 1 1 d . . . . .
H13A H 0.512921 0.841049 0.444413 0.065 Uiso 1 1 calc R U . . .
H13B H 0.482615 0.941196 0.423302 0.065 Uiso 1 1 calc R U . . .
H13C H 0.443939 0.850043 0.394973 0.065 Uiso 1 1 calc R U . . .
C14 C -0.14271(18) 0.65987(13) 0.49326(7) 0.0371(4) Uani 1 1 d . . . . .
C15 C -0.1299(3) 0.57786(15) 0.52725(8) 0.0600(7) Uani 1 1 d . . . . .
H15A H -0.051380 0.570535 0.540065 0.090 Uiso 1 1 calc R U . . .
H15B H -0.157056 0.520742 0.511756 0.090 Uiso 1 1 calc R U . . .
H15C H -0.173312 0.590767 0.551297 0.090 Uiso 1 1 calc R U . . .
C16 C -0.0977(2) 0.62973(15) 0.44988(8) 0.0524(6) Uani 1 1 d . . . . .
H16A H -0.102612 0.681962 0.428943 0.079 Uiso 1 1 calc R U . . .
H16B H -0.142294 0.578022 0.435830 0.079 Uiso 1 1 calc R U . . .
H16C H -0.019996 0.610262 0.457579 0.079 Uiso 1 1 calc R U . . .
C17 C -0.26501(18) 0.69393(19) 0.48164(7) 0.0527(6) Uani 1 1 d . . . . .
H17A H -0.270786 0.736938 0.455846 0.063 Uiso 1 1 calc R U . . .
H17B H -0.313586 0.640104 0.472412 0.063 Uiso 1 1 calc R U . . .
C18 C -0.30755(19) 0.7437(2) 0.52120(8) 0.0579(7) Uani 1 1 d . . . . .
H18A H -0.385419 0.763961 0.511935 0.069 Uiso 1 1 calc R U . . .
H18B H -0.305481 0.700554 0.546810 0.069 Uiso 1 1 calc R U . . .
C19 C -0.2329(2) 0.82852(17) 0.53540(8) 0.0520(6) Uani 1 1 d . . . . .
H19A H -0.261180 0.860531 0.560349 0.062 Uiso 1 1 calc R U . . .
H19B H -0.238661 0.872241 0.509879 0.062 Uiso 1 1 calc R U . . .
C20 C -0.10816(18) 0.80368(14) 0.55053(7) 0.0382(4) Uani 1 1 d . . . . .
C21 C -0.0892(2) 0.75153(16) 0.59609(7) 0.0459(5) Uani 1 1 d . . . . .
H21A H -0.141729 0.699849 0.595012 0.069 Uiso 1 1 calc R U . . .
H21B H -0.100993 0.794175 0.620160 0.069 Uiso 1 1 calc R U . . .
H21C H -0.012971 0.727675 0.601847 0.069 Uiso 1 1 calc R U . . .
C22 C -0.0357(3) 0.89219(19) 0.55441(10) 0.0752(9) Uani 1 1 d . . . . .
H22A H 0.042492 0.875318 0.563656 0.113 Uiso 1 1 calc R U . . .
H22B H -0.059373 0.933815 0.576757 0.113 Uiso 1 1 calc R U . . .
H22C H -0.044238 0.923501 0.525286 0.113 Uiso 1 1 calc R U . . .
Br2 Br 0.6844(7) 0.5154(6) 0.1704(2) 0.0293(5) Uani 0.25 1 d D U P B 2
Ni2 Ni 0.69727(2) 0.62185(2) 0.23301(2) 0.02187(7) Uani 1 1 d D . . . .
Cl2 Cl 0.6769(5) 0.5099(5) 0.17758(16) 0.0293(5) Uani 0.75 1 d D U P B 1
P2 P 0.53895(3) 0.68037(3) 0.20742(2) 0.02399(9) Uani 1 1 d . . . . .
O4 O 0.50580(10) 0.75641(8) 0.24520(4) 0.0303(3) Uani 1 1 d . . . . .
O5 O 0.84617(9) 0.58472(8) 0.26108(4) 0.0253(2) Uani 1 1 d . . . . .
O6 O 0.66720(11) 0.92948(9) 0.37531(4) 0.0336(3) Uani 1 1 d . . . . .
N2 N 0.88703(12) 0.49550(9) 0.25119(5) 0.0216(3) Uani 1 1 d . . . . .
H2 H 0.8393(17) 0.4738(13) 0.2279(7) 0.025(5) Uiso 1 1 d . . . . .
C23 C 0.59738(14) 0.76965(11) 0.28053(6) 0.0247(3) Uani 1 1 d . . . . .
C24 C 0.69379(14) 0.71357(11) 0.27982(5) 0.0231(3) Uani 1 1 d . . . . .
C25 C 0.78304(14) 0.73209(11) 0.31521(6) 0.0251(3) Uani 1 1 d . . . . .
H25 H 0.848634 0.695815 0.317120 0.030 Uiso 1 1 calc R U . . .
C26 C 0.77813(14) 0.80270(12) 0.34786(5) 0.0255(3) Uani 1 1 d . . . . .
H26 H 0.839891 0.813733 0.370587 0.031 Uiso 1 1 calc R U . . .
C27 C 0.68009(15) 0.85610(11) 0.34597(6) 0.0255(3) Uani 1 1 d . . . . .
C28 C 0.58689(14) 0.83870(12) 0.31250(6) 0.0270(3) Uani 1 1 d . . . . .
H28 H 0.519741 0.872508 0.311701 0.032 Uiso 1 1 calc R U . . .
C29 C 0.76501(18) 0.95926(14) 0.40538(6) 0.0397(4) Uani 1 1 d . . . . .
H29A H 0.824980 0.972595 0.388123 0.060 Uiso 1 1 calc R U . . .
H29B H 0.788684 0.910089 0.427150 0.060 Uiso 1 1 calc R U . . .
H29C H 0.747632 1.015271 0.421257 0.060 Uiso 1 1 calc R U . . .
C30 C 0.41674(14) 0.60138(12) 0.19978(6) 0.0293(4) Uani 1 1 d . . . . .
H30 H 0.428438 0.554488 0.176577 0.035 Uiso 1 1 calc R U . . .
C31 C 0.41205(18) 0.54860(14) 0.24446(7) 0.0400(4) Uani 1 1 d . . . . .
H31A H 0.482927 0.516843 0.253974 0.060 Uiso 1 1 calc R U . . .
H31B H 0.351741 0.502992 0.239856 0.060 Uiso 1 1 calc R U . . .
H31C H 0.398520 0.592761 0.267659 0.060 Uiso 1 1 calc R U . . .
C32 C 0.30401(15) 0.65145(15) 0.18328(8) 0.0409(5) Uani 1 1 d . . . . .
H32A H 0.289871 0.697388 0.205607 0.061 Uiso 1 1 calc R U . . .
H32B H 0.243666 0.605855 0.179177 0.061 Uiso 1 1 calc R U . . .
H32C H 0.307784 0.682520 0.154701 0.061 Uiso 1 1 calc R U . . .
C33 C 0.52705(16) 0.75389(13) 0.15609(6) 0.0334(4) Uani 1 1 d . . . . .
H33 H 0.457686 0.791643 0.154610 0.040 Uiso 1 1 calc R U . . .
C34 C 0.62764(19) 0.82246(16) 0.16046(8) 0.0494(5) Uani 1 1 d . . . . .
H34A H 0.631019 0.858160 0.188235 0.074 Uiso 1 1 calc R U . . .
H34B H 0.618125 0.864771 0.134775 0.074 Uiso 1 1 calc R U . . .
H34C H 0.696778 0.787388 0.161102 0.074 Uiso 1 1 calc R U . . .
C35 C 0.5170(2) 0.69533(16) 0.11221(7) 0.0454(5) Uani 1 1 d . . . . .
H35A H 0.584736 0.658630 0.112394 0.068 Uiso 1 1 calc R U . . .
H35B H 0.507061 0.736776 0.086196 0.068 Uiso 1 1 calc R U . . .
H35C H 0.452769 0.653821 0.110487 0.068 Uiso 1 1 calc R U . . .
C36 C 1.00282(14) 0.50578(12) 0.23499(6) 0.0262(3) Uani 1 1 d . . . . .
C37 C 1.08440(15) 0.56290(14) 0.26919(6) 0.0335(4) Uani 1 1 d . . . . .
H37A H 1.044335 0.614438 0.280494 0.050 Uiso 1 1 calc R U . . .
H37B H 1.144496 0.587281 0.254397 0.050 Uiso 1 1 calc R U . . .
H37C H 1.115835 0.523006 0.294233 0.050 Uiso 1 1 calc R U . . .
C38 C 0.97924(16) 0.55909(14) 0.18962(6) 0.0351(4) Uani 1 1 d . . . . .
H38A H 0.924199 0.524980 0.168662 0.053 Uiso 1 1 calc R U . . .
H38B H 1.048309 0.564919 0.176967 0.053 Uiso 1 1 calc R U . . .
H38C H 0.950385 0.620889 0.194719 0.053 Uiso 1 1 calc R U . . .
C39 C 1.04739(16) 0.40673(13) 0.22719(6) 0.0338(4) Uani 1 1 d . . . . .
H39A H 1.000957 0.379266 0.200599 0.041 Uiso 1 1 calc R U . . .
H39B H 1.124192 0.412052 0.220475 0.041 Uiso 1 1 calc R U . . .
C40 C 1.04779(17) 0.34034(14) 0.26756(7) 0.0386(4) Uani 1 1 d . . . . .
H40A H 1.097998 0.364668 0.293948 0.046 Uiso 1 1 calc R U . . .
H40B H 1.075248 0.278580 0.260155 0.046 Uiso 1 1 calc R U . . .
C41 C 0.92777(17) 0.33185(12) 0.27858(7) 0.0347(4) Uani 1 1 d . . . . .
H41A H 0.928574 0.289133 0.304278 0.042 Uiso 1 1 calc R U . . .
H41B H 0.879607 0.304115 0.252507 0.042 Uiso 1 1 calc R U . . .
C42 C 0.87621(15) 0.42608(12) 0.29020(6) 0.0280(4) Uani 1 1 d . . . . .
C43 C 0.93285(18) 0.46582(14) 0.33611(6) 0.0365(4) Uani 1 1 d . . . . .
H43A H 1.013815 0.462720 0.337860 0.055 Uiso 1 1 calc R U . . .
H43B H 0.910185 0.429315 0.360510 0.055 Uiso 1 1 calc R U . . .
H43C H 0.910153 0.530422 0.338816 0.055 Uiso 1 1 calc R U . . .
C44 C 0.74972(16) 0.41442(14) 0.29082(7) 0.0373(4) Uani 1 1 d . . . . .
H44A H 0.717531 0.474378 0.296969 0.056 Uiso 1 1 calc R U . . .
H44B H 0.738191 0.370134 0.314251 0.056 Uiso 1 1 calc R U . . .
H44C H 0.713589 0.391404 0.261629 0.056 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 2.374(6) . ?
Ni1 Cl1 2.253(5) . ?
Ni1 P1 2.0892(5) . ?
Ni1 O2 1.9115(13) . ?
Ni1 C2 1.8979(18) . ?
P1 O1 1.6438(14) . ?
P1 C8 1.8304(19) . ?
P1 C11 1.8213(19) . ?
O1 C1 1.393(2) . ?
O2 N1 1.3902(19) . ?
O3 C5 1.372(2) . ?
O3 C7 1.430(3) . ?
N1 H1 0.97(2) . ?
N1 C14 1.536(2) . ?
N1 C20 1.533(2) . ?
C1 C2 1.402(2) . ?
C1 C6 1.374(3) . ?
C2 C3 1.389(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.393(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.380(3) . ?
C5 C6 1.393(3) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8 0.9800 . ?
C8 C9 1.529(3) . ?
C8 C10 1.515(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11 0.9800 . ?
C11 C12 1.529(3) . ?
C11 C13 1.521(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.527(3) . ?
C14 C16 1.527(3) . ?
C14 C17 1.524(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.519(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.514(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.527(3) . ?
C20 C21 1.522(3) . ?
C20 C22 1.516(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
Br2 Ni2 2.373(8) . ?
Ni2 Cl2 2.266(6) . ?
Ni2 P2 2.0927(5) . ?
Ni2 O5 1.9132(11) . ?
Ni2 C24 1.9026(16) . ?
P2 O4 1.6432(12) . ?
P2 C30 1.8226(17) . ?
P2 C33 1.8276(18) . ?
O4 C23 1.402(2) . ?
O5 N2 1.4001(16) . ?
O6 C27 1.377(2) . ?
O6 C29 1.417(2) . ?
N2 H2 0.88(2) . ?
N2 C36 1.537(2) . ?
N2 C42 1.536(2) . ?
C23 C24 1.400(2) . ?
C23 C28 1.379(2) . ?
C24 C25 1.397(2) . ?
C25 H25 0.9300 . ?
C25 C26 1.397(2) . ?
C26 H26 0.9300 . ?
C26 C27 1.386(2) . ?
C27 C28 1.391(2) . ?
C28 H28 0.9300 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30 0.9800 . ?
C30 C31 1.527(3) . ?
C30 C32 1.531(2) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 H33 0.9800 . ?
C33 C34 1.533(3) . ?
C33 C35 1.529(3) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 C37 1.522(2) . ?
C36 C38 1.527(2) . ?
C36 C39 1.529(2) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C39 C40 1.519(3) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C40 C41 1.521(3) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C41 C42 1.529(2) . ?
C42 C43 1.527(3) . ?
C42 C44 1.521(3) . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
P1 Ni1 Br1 87.08(13) . . ?
P1 Ni1 Cl1 92.95(9) . . ?
O2 Ni1 Br1 101.25(14) . . ?
O2 Ni1 Cl1 95.50(10) . . ?
O2 Ni1 P1 171.31(5) . . ?
C2 Ni1 Br1 169.98(15) . . ?
C2 Ni1 Cl1 174.16(15) . . ?
C2 Ni1 P1 82.97(6) . . ?
C2 Ni1 O2 88.75(7) . . ?
O1 P1 Ni1 107.95(5) . . ?
O1 P1 C8 99.63(9) . . ?
O1 P1 C11 103.03(8) . . ?
C8 P1 Ni1 119.21(7) . . ?
C11 P1 Ni1 117.77(6) . . ?
C11 P1 C8 106.53(9) . . ?
C1 O1 P1 111.00(11) . . ?
N1 O2 Ni1 119.67(10) . . ?
C5 O3 C7 116.49(17) . . ?
O2 N1 H1 105.0(12) . . ?
O2 N1 C14 110.50(14) . . ?
O2 N1 C20 109.49(14) . . ?
C14 N1 H1 107.6(12) . . ?
C20 N1 H1 104.6(12) . . ?
C20 N1 C14 118.56(14) . . ?
O1 C1 C2 117.25(16) . . ?
C6 C1 O1 118.58(16) . . ?
C6 C1 C2 124.16(17) . . ?
C1 C2 Ni1 120.45(13) . . ?
C3 C2 Ni1 124.58(14) . . ?
C3 C2 C1 114.94(17) . . ?
C2 C3 H3 118.6 . . ?
C2 C3 C4 122.85(18) . . ?
C4 C3 H3 118.6 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.47(18) . . ?
C5 C4 H4 120.3 . . ?
O3 C5 C4 123.79(18) . . ?
O3 C5 C6 116.20(17) . . ?
C4 C5 C6 120.01(17) . . ?
C1 C6 C5 118.44(17) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
O3 C7 H7A 109.5 . . ?
O3 C7 H7B 109.5 . . ?
O3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
P1 C8 H8 107.0 . . ?
C9 C8 P1 109.11(14) . . ?
C9 C8 H8 107.0 . . ?
C10 C8 P1 114.43(17) . . ?
C10 C8 H8 107.0 . . ?
C10 C8 C9 111.99(18) . . ?
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 . . ?
P1 C11 H11 107.4 . . ?
C12 C11 P1 108.51(13) . . ?
C12 C11 H11 107.4 . . ?
C13 C11 P1 114.01(14) . . ?
C13 C11 H11 107.4 . . ?
C13 C11 C12 111.73(16) . . ?
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 . . ?
C15 C14 N1 110.82(17) . . ?
C16 C14 N1 105.87(16) . . ?
C16 C14 C15 109.22(18) . . ?
C17 C14 N1 107.86(16) . . ?
C17 C14 C15 112.50(19) . . ?
C17 C14 C16 110.37(18) . . ?
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 . . ?
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 . . ?
C14 C17 H17A 108.9 . . ?
C14 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C18 C17 C14 113.31(18) . . ?
C18 C17 H17A 108.9 . . ?
C18 C17 H17B 108.9 . . ?
C17 C18 H18A 109.8 . . ?
C17 C18 H18B 109.8 . . ?
H18A C18 H18B 108.3 . . ?
C19 C18 C17 109.18(18) . . ?
C19 C18 H18A 109.8 . . ?
C19 C18 H18B 109.8 . . ?
C18 C19 H19A 108.8 . . ?
C18 C19 H19B 108.8 . . ?
C18 C19 C20 113.76(18) . . ?
H19A C19 H19B 107.7 . . ?
C20 C19 H19A 108.8 . . ?
C20 C19 H19B 108.8 . . ?
C19 C20 N1 107.56(16) . . ?
C21 C20 N1 111.45(16) . . ?
C21 C20 C19 112.01(18) . . ?
C22 C20 N1 105.92(17) . . ?
C22 C20 C19 110.5(2) . . ?
C22 C20 C21 109.20(19) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
P2 Ni2 Br2 91.4(2) . . ?
P2 Ni2 Cl2 91.47(17) . . ?
O5 Ni2 Br2 96.2(2) . . ?
O5 Ni2 Cl2 96.31(17) . . ?
O5 Ni2 P2 171.90(4) . . ?
C24 Ni2 Br2 174.0(2) . . ?
C24 Ni2 Cl2 172.50(16) . . ?
C24 Ni2 P2 82.70(5) . . ?
C24 Ni2 O5 89.73(6) . . ?
O4 P2 Ni2 108.17(5) . . ?
O4 P2 C30 102.31(7) . . ?
O4 P2 C33 101.35(8) . . ?
C30 P2 Ni2 117.48(6) . . ?
C30 P2 C33 106.77(8) . . ?
C33 P2 Ni2 118.35(6) . . ?
C23 O4 P2 110.64(10) . . ?
N2 O5 Ni2 119.12(9) . . ?
C27 O6 C29 117.27(14) . . ?
O5 N2 H2 105.9(12) . . ?
O5 N2 C36 109.80(12) . . ?
O5 N2 C42 110.29(11) . . ?
C36 N2 H2 107.1(12) . . ?
C42 N2 H2 104.2(12) . . ?
C42 N2 C36 118.63(13) . . ?
C24 C23 O4 117.36(14) . . ?
C28 C23 O4 117.56(14) . . ?
C28 C23 C24 125.05(16) . . ?
C23 C24 Ni2 120.56(12) . . ?
C25 C24 Ni2 124.96(12) . . ?
C25 C24 C23 114.48(15) . . ?
C24 C25 H25 118.5 . . ?
C24 C25 C26 122.91(15) . . ?
C26 C25 H25 118.5 . . ?
C25 C26 H26 120.4 . . ?
C27 C26 C25 119.19(16) . . ?
C27 C26 H26 120.4 . . ?
O6 C27 C26 124.18(15) . . ?
O6 C27 C28 115.27(15) . . ?
C26 C27 C28 120.54(15) . . ?
C23 C28 C27 117.78(15) . . ?
C23 C28 H28 121.1 . . ?
C27 C28 H28 121.1 . . ?
O6 C29 H29A 109.5 . . ?
O6 C29 H29B 109.5 . . ?
O6 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
P2 C30 H30 107.7 . . ?
C31 C30 P2 109.20(13) . . ?
C31 C30 H30 107.7 . . ?
C31 C30 C32 110.71(15) . . ?
C32 C30 P2 113.68(13) . . ?
C32 C30 H30 107.7 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
P2 C33 H33 107.6 . . ?
C34 C33 P2 109.36(13) . . ?
C34 C33 H33 107.6 . . ?
C35 C33 P2 112.51(13) . . ?
C35 C33 H33 107.6 . . ?
C35 C33 C34 111.82(17) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C37 C36 N2 110.82(13) . . ?
C37 C36 C38 109.46(15) . . ?
C37 C36 C39 112.67(15) . . ?
C38 C36 N2 105.61(13) . . ?
C38 C36 C39 109.93(14) . . ?
C39 C36 N2 108.10(13) . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C36 C39 H39A 108.8 . . ?
C36 C39 H39B 108.8 . . ?
H39A C39 H39B 107.6 . . ?
C40 C39 C36 114.00(15) . . ?
C40 C39 H39A 108.8 . . ?
C40 C39 H39B 108.8 . . ?
C39 C40 H40A 109.8 . . ?
C39 C40 H40B 109.8 . . ?
C39 C40 C41 109.22(15) . . ?
H40A C40 H40B 108.3 . . ?
C41 C40 H40A 109.8 . . ?
C41 C40 H40B 109.8 . . ?
C40 C41 H41A 108.8 . . ?
C40 C41 H41B 108.8 . . ?
C40 C41 C42 113.83(15) . . ?
H41A C41 H41B 107.7 . . ?
C42 C41 H41A 108.8 . . ?
C42 C41 H41B 108.8 . . ?
C41 C42 N2 107.75(13) . . ?
C43 C42 N2 110.82(14) . . ?
C43 C42 C41 112.53(15) . . ?
C44 C42 N2 106.13(14) . . ?
C44 C42 C41 110.04(15) . . ?
C44 C42 C43 109.37(15) . . ?
C42 C43 H43A 109.5 . . ?
C42 C43 H43B 109.5 . . ?
C42 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C42 C44 H44A 109.5 . . ?
C42 C44 H44B 109.5 . . ?
C42 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 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
Br1 Ni1 C2 C1 -7.5(12) . . . . ?
Br1 Ni1 C2 C3 174.5(11) . . . . ?
Ni1 P1 O1 C1 5.77(12) . . . . ?
Ni1 P1 C8 C9 -47.99(18) . . . . ?
Ni1 P1 C8 C10 78.35(18) . . . . ?
Ni1 P1 C11 C12 43.96(16) . . . . ?
Ni1 P1 C11 C13 169.17(12) . . . . ?
Ni1 O2 N1 C14 102.86(15) . . . . ?
Ni1 O2 N1 C20 -124.78(13) . . . . ?
Ni1 C2 C3 C4 176.20(15) . . . . ?
P1 Ni1 C2 C1 -0.87(14) . . . . ?
P1 Ni1 C2 C3 -178.80(17) . . . . ?
P1 O1 C1 C2 -6.89(19) . . . . ?
P1 O1 C1 C6 172.53(13) . . . . ?
O1 P1 C8 C9 68.94(17) . . . . ?
O1 P1 C8 C10 -164.72(17) . . . . ?
O1 P1 C11 C12 -74.68(15) . . . . ?
O1 P1 C11 C13 50.53(15) . . . . ?
O1 C1 C2 Ni1 5.0(2) . . . . ?
O1 C1 C2 C3 -176.87(16) . . . . ?
O1 C1 C6 C5 178.30(16) . . . . ?
O2 Ni1 C2 C1 176.49(15) . . . . ?
O2 Ni1 C2 C3 -1.44(17) . . . . ?
O2 N1 C14 C15 53.6(2) . . . . ?
O2 N1 C14 C16 -64.68(19) . . . . ?
O2 N1 C14 C17 177.18(14) . . . . ?
O2 N1 C20 C19 -177.32(15) . . . . ?
O2 N1 C20 C21 -54.2(2) . . . . ?
O2 N1 C20 C22 64.5(2) . . . . ?
O3 C5 C6 C1 178.92(16) . . . . ?
N1 C14 C17 C18 -52.9(2) . . . . ?
C1 C2 C3 C4 -1.8(3) . . . . ?
C2 C1 C6 C5 -2.3(3) . . . . ?
C2 C3 C4 C5 -1.4(3) . . . . ?
C3 C4 C5 O3 -177.17(18) . . . . ?
C3 C4 C5 C6 2.9(3) . . . . ?
C4 C5 C6 C1 -1.2(3) . . . . ?
C6 C1 C2 Ni1 -174.38(14) . . . . ?
C6 C1 C2 C3 3.7(3) . . . . ?
C7 O3 C5 C4 1.6(3) . . . . ?
C7 O3 C5 C6 -178.5(2) . . . . ?
C8 P1 O1 C1 -119.35(12) . . . . ?
C8 P1 C11 C12 -179.02(15) . . . . ?
C8 P1 C11 C13 -53.81(17) . . . . ?
C11 P1 O1 C1 131.05(12) . . . . ?
C11 P1 C8 C9 175.73(15) . . . . ?
C11 P1 C8 C10 -57.93(19) . . . . ?
C14 N1 C20 C19 -49.3(2) . . . . ?
C14 N1 C20 C21 73.8(2) . . . . ?
C14 N1 C20 C22 -167.52(19) . . . . ?
C14 C17 C18 C19 59.3(3) . . . . ?
C15 C14 C17 C18 69.6(3) . . . . ?
C16 C14 C17 C18 -168.12(19) . . . . ?
C17 C18 C19 C20 -59.4(3) . . . . ?
C18 C19 C20 N1 52.8(2) . . . . ?
C18 C19 C20 C21 -70.0(2) . . . . ?
C18 C19 C20 C22 167.95(19) . . . . ?
C20 N1 C14 C15 -73.9(2) . . . . ?
C20 N1 C14 C16 167.80(17) . . . . ?
C20 N1 C14 C17 49.7(2) . . . . ?
Ni2 P2 O4 C23 7.57(12) . . . . ?
Ni2 P2 C30 C31 52.85(14) . . . . ?
Ni2 P2 C30 C32 177.02(11) . . . . ?
Ni2 P2 C33 C34 -44.92(16) . . . . ?
Ni2 P2 C33 C35 79.98(15) . . . . ?
Ni2 O5 N2 C36 126.77(11) . . . . ?
Ni2 O5 N2 C42 -100.70(13) . . . . ?
Ni2 C24 C25 C26 177.51(12) . . . . ?
P2 O4 C23 C24 -4.62(18) . . . . ?
P2 O4 C23 C28 173.53(12) . . . . ?
O4 P2 C30 C31 -65.41(13) . . . . ?
O4 P2 C30 C32 58.76(15) . . . . ?
O4 P2 C33 C34 73.10(15) . . . . ?
O4 P2 C33 C35 -162.00(14) . . . . ?
O4 C23 C24 Ni2 -1.1(2) . . . . ?
O4 C23 C24 C25 178.30(14) . . . . ?
O4 C23 C28 C27 -176.12(15) . . . . ?
O5 N2 C36 C37 52.90(17) . . . . ?
O5 N2 C36 C38 -65.54(16) . . . . ?
O5 N2 C36 C39 176.83(13) . . . . ?
O5 N2 C42 C41 -177.06(13) . . . . ?
O5 N2 C42 C43 -53.55(17) . . . . ?
O5 N2 C42 C44 65.09(16) . . . . ?
O6 C27 C28 C23 176.30(15) . . . . ?
N2 C36 C39 C40 -51.8(2) . . . . ?
C23 C24 C25 C26 -1.9(2) . . . . ?
C24 C23 C28 C27 1.9(3) . . . . ?
C24 C25 C26 C27 1.2(2) . . . . ?
C25 C26 C27 O6 -177.65(15) . . . . ?
C25 C26 C27 C28 1.1(2) . . . . ?
C26 C27 C28 C23 -2.5(2) . . . . ?
C28 C23 C24 Ni2 -179.12(13) . . . . ?
C28 C23 C24 C25 0.3(2) . . . . ?
C29 O6 C27 C26 8.2(2) . . . . ?
C29 O6 C27 C28 -170.61(16) . . . . ?
C30 P2 O4 C23 132.24(12) . . . . ?
C30 P2 C33 C34 179.82(14) . . . . ?
C30 P2 C33 C35 -55.29(16) . . . . ?
C33 P2 O4 C23 -117.58(12) . . . . ?
C33 P2 C30 C31 -171.44(13) . . . . ?
C33 P2 C30 C32 -47.27(15) . . . . ?
C36 N2 C42 C41 -49.24(19) . . . . ?
C36 N2 C42 C43 74.27(18) . . . . ?
C36 N2 C42 C44 -167.08(14) . . . . ?
C36 C39 C40 C41 58.2(2) . . . . ?
C37 C36 C39 C40 71.0(2) . . . . ?
C38 C36 C39 C40 -166.63(16) . . . . ?
C39 C40 C41 C42 -58.8(2) . . . . ?
C40 C41 C42 N2 52.8(2) . . . . ?
C40 C41 C42 C43 -69.6(2) . . . . ?
C40 C41 C42 C44 168.13(16) . . . . ?
C42 N2 C36 C37 -75.15(18) . . . . ?
C42 N2 C36 C38 166.41(14) . . . . ?
C42 N2 C36 C39 48.78(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
####################################################################### 
# 
# 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_rajib941
_database_code_depnum_ccdc_archive 'CCDC 2287104'
loop_
_audit_author_name
_audit_author_address
'Rajib Kumar Sarker'
;University of Montreal
Canada
;
_audit_update_record             
;
2023-08-06 deposited with the CCDC.	2024-05-24 downloaded from the CCDC.
;
_audit_creation_date             2023-08-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H37 F3 N Ni O4 P'
_chemical_formula_sum            'C23 H37 F3 N Ni O4 P'
_chemical_formula_weight         538.21
_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 0.0137 0.0067 '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 0.0583 0.0400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -1.3357 3.2904 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2543 0.3332 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   15.7583(5)
_cell_length_b                   12.7241(4)
_cell_length_c                   14.1830(5)
_cell_angle_alpha                90
_cell_angle_beta                 115.546(2)
_cell_angle_gamma                90
_cell_volume                     2565.82(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8303
_cell_measurement_temperature    150
_cell_measurement_theta_max      50.181
_cell_measurement_theta_min      2.704
_shelx_estimated_absorpt_T_max   0.653
_shelx_estimated_absorpt_T_min   0.537
_exptl_absorpt_coefficient_mu    4.797
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1104 before and 0.0883 after correction.
The Ratio of minimum to maximum transmission is 0.8752.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.148
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.097
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon III CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0835
_diffrn_reflns_av_unetI/netI     0.0735
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24214
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.053
_diffrn_reflns_theta_min         2.704
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            'Bruker CMOS Photon III '
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_current           2.86
_diffrn_source_power             0.19945639999999998
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_source_voltage           69.74
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3409
_reflns_number_total             4845
_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 (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4845
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0568
_refine_ls_restrained_S_all      1.050
_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)+(0.0239P)²+5.1598P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1291
_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:
 C7(H7), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C),
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C)
;
_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
Ni1 Ni 0.23883(4) 0.46741(4) 0.73647(4) 0.03155(17) Uani 1 1 d . . . . .
P1 P 0.27004(8) 0.32292(9) 0.81798(8) 0.0353(3) Uani 1 1 d . . . . .
F1 F 0.49350(19) 0.4167(2) 0.5859(2) 0.0603(8) Uani 1 1 d . . . . .
F2 F 0.5324(2) 0.5109(3) 0.7214(3) 0.0921(12) Uani 1 1 d . . . . .
F3 F 0.4193(2) 0.5571(2) 0.5751(3) 0.0925(12) Uani 1 1 d . . . . .
O1 O 0.1827(2) 0.2978(3) 0.8489(2) 0.0490(8) Uani 1 1 d . . . . .
O2 O 0.19612(19) 0.6011(2) 0.6742(2) 0.0398(7) Uani 1 1 d . . . . .
O3 O 0.3412(2) 0.4782(2) 0.6950(2) 0.0458(8) Uani 1 1 d . . . . .
O4 O 0.3928(3) 0.3226(3) 0.6668(4) 0.0939(15) Uani 1 1 d . . . . .
N1 N 0.2304(3) 0.6425(3) 0.6067(3) 0.0341(8) Uani 1 1 d . . . . .
H1 H 0.273(3) 0.601(3) 0.612(3) 0.039(13) Uiso 1 1 d . . . . .
C1 C 0.1242(3) 0.3845(4) 0.8311(3) 0.0432(11) Uani 1 1 d . . . . .
C2 C 0.1398(3) 0.4701(3) 0.7793(3) 0.0354(10) Uani 1 1 d . . . . .
C3 C 0.0800(3) 0.5555(4) 0.7639(3) 0.0467(12) Uani 1 1 d . . . . .
H3 H 0.086778 0.615274 0.727677 0.056 Uiso 1 1 calc R U . . .
C4 C 0.0107(3) 0.5562(5) 0.7998(4) 0.0593(15) Uani 1 1 d . . . . .
H4 H -0.028064 0.616288 0.789355 0.071 Uiso 1 1 calc R U . . .
C5 C -0.0016(3) 0.4686(6) 0.8511(4) 0.0681(17) Uani 1 1 d . . . . .
H5 H -0.049222 0.468684 0.875259 0.082 Uiso 1 1 calc R U . . .
C6 C 0.0550(3) 0.3818(5) 0.8671(4) 0.0563(14) Uani 1 1 d . . . . .
H6 H 0.046931 0.321508 0.901931 0.068 Uiso 1 1 calc R U . . .
C7 C 0.2752(3) 0.2009(3) 0.7539(3) 0.0438(11) Uani 1 1 d . . . . .
H7 H 0.335429 0.200979 0.746271 0.053 Uiso 1 1 calc R U . . .
C8 C 0.1948(4) 0.1963(4) 0.6448(4) 0.0587(14) Uani 1 1 d . . . . .
H8A H 0.134763 0.193361 0.649930 0.088 Uiso 1 1 calc R U . . .
H8B H 0.201477 0.133379 0.608661 0.088 Uiso 1 1 calc R U . . .
H8C H 0.196227 0.259011 0.605445 0.088 Uiso 1 1 calc R U . . .
C9 C 0.2756(4) 0.1033(4) 0.8182(4) 0.0603(14) Uani 1 1 d . . . . .
H9A H 0.329396 0.106898 0.887042 0.090 Uiso 1 1 calc R U . . .
H9B H 0.280495 0.039850 0.781695 0.090 Uiso 1 1 calc R U . . .
H9C H 0.217147 0.101057 0.826734 0.090 Uiso 1 1 calc R U . . .
C10 C 0.3702(3) 0.3227(4) 0.9457(3) 0.0437(11) Uani 1 1 d . . . . .
H10 H 0.367078 0.257136 0.982863 0.052 Uiso 1 1 calc R U . . .
C11 C 0.3646(4) 0.4163(4) 1.0100(4) 0.0635(15) Uani 1 1 d . . . . .
H11A H 0.368499 0.481709 0.975615 0.095 Uiso 1 1 calc R U . . .
H11B H 0.416944 0.413106 1.079976 0.095 Uiso 1 1 calc R U . . .
H11C H 0.304881 0.414103 1.015743 0.095 Uiso 1 1 calc R U . . .
C12 C 0.4636(3) 0.3217(4) 0.9362(4) 0.0625(14) Uani 1 1 d . . . . .
H12A H 0.466099 0.259369 0.896830 0.094 Uiso 1 1 calc R U . . .
H12B H 0.516008 0.319859 1.006087 0.094 Uiso 1 1 calc R U . . .
H12C H 0.468189 0.385106 0.899465 0.094 Uiso 1 1 calc R U . . .
C13 C 0.1584(4) 0.6293(5) 0.4936(3) 0.0589(14) Uani 1 1 d . . . . .
C14 C 0.0638(4) 0.6761(6) 0.4766(5) 0.084(2) Uani 1 1 d . . . . .
H14A H 0.047814 0.653306 0.532889 0.126 Uiso 1 1 calc R U . . .
H14B H 0.015222 0.652093 0.409278 0.126 Uiso 1 1 calc R U . . .
H14C H 0.067701 0.752969 0.476541 0.126 Uiso 1 1 calc R U . . .
C15 C 0.1452(5) 0.5119(5) 0.4742(5) 0.088(2) Uani 1 1 d . . . . .
H15A H 0.206463 0.478625 0.493080 0.132 Uiso 1 1 calc R U . . .
H15B H 0.104523 0.499101 0.400062 0.132 Uiso 1 1 calc R U . . .
H15C H 0.115969 0.482064 0.516750 0.132 Uiso 1 1 calc R U . . .
C16 C 0.1990(5) 0.6802(7) 0.4253(5) 0.099(2) Uani 1 1 d . . . . .
H16A H 0.149770 0.681725 0.352390 0.119 Uiso 1 1 calc R U . . .
H16B H 0.251180 0.635877 0.426740 0.119 Uiso 1 1 calc R U . . .
C17 C 0.2354(6) 0.7910(6) 0.4575(6) 0.109(3) Uani 1 1 d . . . . .
H17A H 0.262577 0.817993 0.410971 0.131 Uiso 1 1 calc R U . . .
H17B H 0.182982 0.837761 0.451042 0.131 Uiso 1 1 calc R U . . .
C18 C 0.3088(5) 0.7902(5) 0.5678(6) 0.085(2) Uani 1 1 d . . . . .
H18A H 0.331786 0.862871 0.588202 0.102 Uiso 1 1 calc R U . . .
H18B H 0.362555 0.747165 0.571808 0.102 Uiso 1 1 calc R U . . .
C19 C 0.2750(4) 0.7476(4) 0.6455(4) 0.0549(13) Uani 1 1 d . . . . .
C20 C 0.2022(5) 0.8224(4) 0.6570(5) 0.0840(19) Uani 1 1 d . . . . .
H20A H 0.159474 0.849664 0.588173 0.126 Uiso 1 1 calc R U . . .
H20B H 0.235156 0.881004 0.703081 0.126 Uiso 1 1 calc R U . . .
H20C H 0.165955 0.783679 0.687117 0.126 Uiso 1 1 calc R U . . .
C21 C 0.3558(4) 0.7298(5) 0.7508(5) 0.0803(18) Uani 1 1 d . . . . .
H21A H 0.331591 0.707842 0.800778 0.120 Uiso 1 1 calc R U . . .
H21B H 0.391575 0.795215 0.775006 0.120 Uiso 1 1 calc R U . . .
H21C H 0.396996 0.674904 0.745170 0.120 Uiso 1 1 calc R U . . .
C22 C 0.3893(3) 0.4182(4) 0.6691(4) 0.0426(11) Uani 1 1 d . . . . .
C23 C 0.4598(3) 0.4766(4) 0.6381(4) 0.0452(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 P1 2.1138(12) . ?
Ni1 O2 1.902(3) . ?
Ni1 O3 1.945(3) . ?
Ni1 C2 1.904(4) . ?
P1 O1 1.646(3) . ?
P1 C7 1.818(5) . ?
P1 C10 1.819(4) . ?
F1 C23 1.322(5) . ?
F2 C23 1.314(6) . ?
F3 C23 1.327(5) . ?
O1 C1 1.390(5) . ?
O2 N1 1.390(4) . ?
O3 C22 1.238(5) . ?
O4 C22 1.218(5) . ?
N1 H1 0.83(4) . ?
N1 C13 1.522(6) . ?
N1 C19 1.500(6) . ?
C1 C2 1.394(6) . ?
C1 C6 1.390(6) . ?
C2 C3 1.392(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.375(8) . ?
C6 H6 0.9500 . ?
C7 H7 1.0000 . ?
C7 C8 1.521(6) . ?
C7 C9 1.539(6) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10 1.0000 . ?
C10 C11 1.525(6) . ?
C10 C12 1.534(6) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.524(7) . ?
C13 C15 1.518(8) . ?
C13 C16 1.516(8) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.516(10) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.492(9) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.516(7) . ?
C19 C20 1.552(7) . ?
C19 C21 1.504(7) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.551(6) . ?

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 169.95(9) . . ?
O2 Ni1 O3 88.28(12) . . ?
O2 Ni1 C2 87.57(16) . . ?
O3 Ni1 P1 101.47(9) . . ?
C2 Ni1 P1 82.57(14) . . ?
C2 Ni1 O3 174.86(16) . . ?
O1 P1 Ni1 106.88(13) . . ?
O1 P1 C7 101.00(18) . . ?
O1 P1 C10 101.58(18) . . ?
C7 P1 Ni1 121.28(15) . . ?
C7 P1 C10 106.8(2) . . ?
C10 P1 Ni1 116.30(16) . . ?
C1 O1 P1 111.3(3) . . ?
N1 O2 Ni1 119.6(2) . . ?
C22 O3 Ni1 137.7(3) . . ?
O2 N1 H1 104(3) . . ?
O2 N1 C13 110.5(3) . . ?
O2 N1 C19 110.1(3) . . ?
C13 N1 H1 103(3) . . ?
C19 N1 H1 108(3) . . ?
C19 N1 C13 120.2(4) . . ?
O1 C1 C2 117.5(3) . . ?
C6 C1 O1 118.6(4) . . ?
C6 C1 C2 123.9(5) . . ?
C1 C2 Ni1 120.6(3) . . ?
C3 C2 Ni1 123.8(3) . . ?
C3 C2 C1 115.6(4) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 C2 122.2(5) . . ?
C4 C3 H3 118.9 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.7(5) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(4) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 120.8 . . ?
C5 C6 C1 118.4(5) . . ?
C5 C6 H6 120.8 . . ?
P1 C7 H7 107.6 . . ?
C8 C7 P1 110.2(3) . . ?
C8 C7 H7 107.6 . . ?
C8 C7 C9 111.1(4) . . ?
C9 C7 P1 112.5(3) . . ?
C9 C7 H7 107.6 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
P1 C10 H10 107.9 . . ?
C11 C10 P1 110.2(3) . . ?
C11 C10 H10 107.9 . . ?
C11 C10 C12 111.4(4) . . ?
C12 C10 P1 111.5(3) . . ?
C12 C10 H10 107.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C14 111.0(4) . . ?
C15 C13 N1 106.3(4) . . ?
C15 C13 C14 107.9(5) . . ?
C16 C13 N1 107.3(4) . . ?
C16 C13 C14 112.6(5) . . ?
C16 C13 C15 111.5(5) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 108.7 . . ?
C13 C16 H16B 108.7 . . ?
C13 C16 C17 114.4(5) . . ?
H16A C16 H16B 107.6 . . ?
C17 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
C16 C17 H17A 109.8 . . ?
C16 C17 H17B 109.8 . . ?
H17A C17 H17B 108.3 . . ?
C18 C17 C16 109.3(5) . . ?
C18 C17 H17A 109.8 . . ?
C18 C17 H17B 109.8 . . ?
C17 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
C17 C18 C19 114.1(5) . . ?
H18A C18 H18B 107.6 . . ?
C19 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
N1 C19 C18 107.9(4) . . ?
N1 C19 C20 109.6(4) . . ?
N1 C19 C21 107.0(4) . . ?
C18 C19 C20 111.4(5) . . ?
C21 C19 C18 111.3(5) . . ?
C21 C19 C20 109.6(5) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O3 C22 C23 113.2(4) . . ?
O4 C22 O3 131.6(4) . . ?
O4 C22 C23 115.1(4) . . ?
F1 C23 F3 105.1(4) . . ?
F1 C23 C22 113.1(4) . . ?
F2 C23 F1 106.9(4) . . ?
F2 C23 F3 109.2(4) . . ?
F2 C23 C22 110.9(4) . . ?
F3 C23 C22 111.4(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ni1 P1 O1 C1 -11.0(3) . . . . ?
Ni1 P1 C7 C8 -42.0(3) . . . . ?
Ni1 P1 C7 C9 -166.5(3) . . . . ?
Ni1 P1 C10 C11 47.9(4) . . . . ?
Ni1 P1 C10 C12 -76.3(4) . . . . ?
Ni1 O2 N1 C13 102.2(4) . . . . ?
Ni1 O2 N1 C19 -122.7(3) . . . . ?
Ni1 O3 C22 O4 -5.7(9) . . . . ?
Ni1 O3 C22 C23 176.9(3) . . . . ?
Ni1 C2 C3 C4 -177.5(3) . . . . ?
P1 O1 C1 C2 8.1(5) . . . . ?
P1 O1 C1 C6 -170.8(3) . . . . ?
O1 P1 C7 C8 75.7(3) . . . . ?
O1 P1 C7 C9 -48.8(4) . . . . ?
O1 P1 C10 C11 -67.7(4) . . . . ?
O1 P1 C10 C12 168.1(3) . . . . ?
O1 C1 C2 Ni1 -0.6(5) . . . . ?
O1 C1 C2 C3 -179.5(4) . . . . ?
O1 C1 C6 C5 178.7(4) . . . . ?
O2 N1 C13 C14 54.2(6) . . . . ?
O2 N1 C13 C15 -62.9(5) . . . . ?
O2 N1 C13 C16 177.6(4) . . . . ?
O2 N1 C19 C18 -178.6(4) . . . . ?
O2 N1 C19 C20 -57.1(5) . . . . ?
O2 N1 C19 C21 61.6(5) . . . . ?
O3 C22 C23 F1 -163.8(4) . . . . ?
O3 C22 C23 F2 76.2(5) . . . . ?
O3 C22 C23 F3 -45.6(6) . . . . ?
O4 C22 C23 F1 18.3(6) . . . . ?
O4 C22 C23 F2 -101.7(5) . . . . ?
O4 C22 C23 F3 136.5(5) . . . . ?
N1 C13 C16 C17 -50.3(7) . . . . ?
C1 C2 C3 C4 1.4(6) . . . . ?
C2 C1 C6 C5 -0.1(7) . . . . ?
C2 C3 C4 C5 -1.3(7) . . . . ?
C3 C4 C5 C6 0.5(7) . . . . ?
C4 C5 C6 C1 0.2(7) . . . . ?
C6 C1 C2 Ni1 178.3(3) . . . . ?
C6 C1 C2 C3 -0.6(6) . . . . ?
C7 P1 O1 C1 -138.7(3) . . . . ?
C7 P1 C10 C11 -173.1(3) . . . . ?
C7 P1 C10 C12 62.7(4) . . . . ?
C10 P1 O1 C1 111.4(3) . . . . ?
C10 P1 C7 C8 -178.5(3) . . . . ?
C10 P1 C7 C9 57.0(4) . . . . ?
C13 N1 C19 C18 -48.5(6) . . . . ?
C13 N1 C19 C20 72.9(5) . . . . ?
C13 N1 C19 C21 -168.3(4) . . . . ?
C13 C16 C17 C18 57.6(8) . . . . ?
C14 C13 C16 C17 72.2(7) . . . . ?
C15 C13 C16 C17 -166.3(6) . . . . ?
C16 C17 C18 C19 -58.1(7) . . . . ?
C17 C18 C19 N1 52.1(7) . . . . ?
C17 C18 C19 C20 -68.2(7) . . . . ?
C17 C18 C19 C21 169.2(6) . . . . ?
C19 N1 C13 C14 -75.7(6) . . . . ?
C19 N1 C13 C15 167.2(4) . . . . ?
C19 N1 C13 C16 47.8(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_vrf_PLAT220_rajib941            
;
RESPONSE
Ueq(min) is observed for C2 part of the phenyl 
ring, while Ueq(max) is observed for C17 on the TEMPO ligand. 
ADPs indicate facile vibrational movement or slight disorder of the 
latter. 
;
_vrf_PLAT241_rajib941            
;
RESPONSE
Atom miss-assignment is not chemically possible. Differences in Ueq are
caused by the whole group vibration  with N1 as pivot point.
;
_vrf_PLAT242_rajib941            
;
RESPONSE
Atom miss-assignment is not chemically possible. Differences in Ueq are
caused by the whole group vibration  with N1 as pivot point. 
(see PLAT220)
;
_vrf_PLAT341_rajib941            
;
RESPONSE
Slightly noisy data, R(sigma) = 7.4%.
;
_vrf_PLAT906_rajib941            
;
RESPONSE
PLATON/TWINROTMAT could not find any twinning. Changing
the absorption correction did not improve the refinement parameters. 
There is no indication of systematic problems with the dataset.
;
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
