# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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. 
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data_L3
_database_code_depnum_ccdc_archive 'CCDC 1877303'
_audit_update_record             
;
2018-11-06 deposited with the CCDC.
2018-12-26 downloaded from the CCDC.
;
_audit_creation_date             2018-04-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C56 H43 F4 N3 O2'
_chemical_formula_sum            'C56 H43 F4 N3 O2'
_chemical_formula_weight         865.93
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   11.3537(4)
_cell_length_b                   23.9312(6)
_cell_length_c                   17.2928(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.819(3)
_cell_angle_gamma                90
_cell_volume                     4520.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18500
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      30.9520
_cell_measurement_theta_min      1.6780
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             17628
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.042
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0798
_diffrn_reflns_av_unetI/netI     0.0929
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            60972
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.537
_diffrn_reflns_theta_min         1.491
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7228
_reflns_number_total             14101
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     590
_refine_ls_number_reflns         14101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1588
_refine_ls_R_factor_gt           0.0715
_refine_ls_restrained_S_all      1.013
_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)+(0.0510P)²+0.8390P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1562
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C32(H32), C15(H15), C54(H54), C51(H51)
2.b Aromatic/amide H refined with riding coordinates:
 C30(H30), C28(H28), C9(H9), C8(H8), C7(H7), C38(H38), C23(H23), C40(H40),
 C24(H24), C5(H5), C3(H3), C34(H34), C27(H27), C26(H26), C41(H41), C47(H47),
 C4(H4), C37(H37), C49(H49), C48(H48), C17(H17), C35(H35), C44(H44), C18(H18),
 C21(H21), C43(H43), C20(H20)
2.c Idealised Me refined as rotating group:
 C56(H56a,H56b,H56c), C55(H55a,H55b,H55c), C53(H53a,H53b,H53c), C52(H52a,H52b,
 H52c)
;
_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
F1 F 1.12854(11) 0.48241(5) 0.63964(7) 0.0521(3) Uani 1 1 d . . . . .
O1 O 0.41539(13) 0.54992(5) 0.39400(9) 0.0474(4) Uani 1 1 d . . . . .
N2 N 0.53466(12) 0.29609(6) 0.36300(8) 0.0241(3) Uani 1 1 d . . . . .
O2 O 0.61279(13) 0.55387(6) 0.43233(10) 0.0511(4) Uani 1 1 d . . . . .
N1 N 0.53893(13) 0.17877(6) 0.33785(8) 0.0264(3) Uani 1 1 d . . . . .
F3 F -0.05241(14) 0.47902(6) 0.09664(9) 0.0812(5) Uani 1 1 d . . . . .
N3 N 0.51646(16) 0.52795(6) 0.40788(9) 0.0346(4) Uani 1 1 d . . . . .
F4 F 0.13354(16) 0.22132(7) 0.53455(11) 0.0949(6) Uani 1 1 d . . . . .
C13 C 0.53236(15) 0.35426(7) 0.37593(10) 0.0236(4) Uani 1 1 d . . . . .
C1 C 0.53321(15) 0.19873(7) 0.40494(10) 0.0239(4) Uani 1 1 d . . . . .
C10 C 0.53933(15) 0.26944(7) 0.50510(10) 0.0248(4) Uani 1 1 d . . . . .
C12 C 0.53739(15) 0.26147(7) 0.41984(10) 0.0234(4) Uani 1 1 d . . . . .
C31 C 0.41856(15) 0.38164(7) 0.35126(10) 0.0243(4) Uani 1 1 d . . . . .
C11 C 0.52804(15) 0.21556(7) 0.53625(10) 0.0257(4) Uani 1 1 d . . . . .
C14 C 0.64262(16) 0.38425(7) 0.40636(10) 0.0263(4) Uani 1 1 d . . . . .
C32 C 0.30401(15) 0.34782(7) 0.31173(10) 0.0269(4) Uani 1 1 d . . . . .
H32 H 0.329565 0.319826 0.278215 0.032 Uiso 1 1 calc R . . . .
C29 C 0.52257(16) 0.46753(7) 0.39573(10) 0.0269(4) Uani 1 1 d . . . . .
C30 C 0.41501(16) 0.43886(7) 0.36300(10) 0.0263(4) Uani 1 1 d . . . . .
H30 H 0.340678 0.457799 0.348924 0.032 Uiso 1 1 calc R . . . .
C45 C 0.53765(18) 0.11960(7) 0.32620(10) 0.0302(4) Uani 1 1 d . . . . .
C2 C 0.52412(16) 0.17204(7) 0.48059(10) 0.0283(4) Uani 1 1 d . . . . .
C28 C 0.63547(17) 0.44166(7) 0.41547(10) 0.0282(4) Uani 1 1 d . . . . .
H28 H 0.706421 0.462596 0.434783 0.034 Uiso 1 1 calc R . . . .
C33 C 0.20511(16) 0.38252(7) 0.25462(11) 0.0300(4) Uani 1 1 d . . . . .
C9 C 0.54685(17) 0.31496(8) 0.55448(11) 0.0317(4) Uani 1 1 d . . . . .
H9 H 0.554103 0.350788 0.535458 0.038 Uiso 1 1 calc R . . . .
C39 C 0.25700(16) 0.31498(8) 0.37290(11) 0.0304(4) Uani 1 1 d . . . . .
C6 C 0.52069(17) 0.20657(8) 0.61504(11) 0.0319(4) Uani 1 1 d . . . . .
C15 C 0.76485(16) 0.35361(8) 0.42533(11) 0.0324(4) Uani 1 1 d . . . . .
H15 H 0.754285 0.318879 0.452721 0.039 Uiso 1 1 calc R . . . .
C22 C 0.86768(17) 0.38631(8) 0.48346(12) 0.0333(4) Uani 1 1 d . . . . .
C50 C 0.42734(19) 0.08998(8) 0.30805(11) 0.0366(5) Uani 1 1 d . . . . .
C8 C 0.54341(18) 0.30649(8) 0.63463(11) 0.0351(5) Uani 1 1 d . . . . .
H8 H 0.549988 0.337284 0.668361 0.042 Uiso 1 1 calc R . . . .
C7 C 0.53069(18) 0.25441(8) 0.66445(11) 0.0358(5) Uani 1 1 d . . . . .
H7 H 0.528623 0.250510 0.717575 0.043 Uiso 1 1 calc R . . . .
C16 C 0.79432(17) 0.33683(9) 0.34759(13) 0.0393(5) Uani 1 1 d . . . . .
F2 F 0.87575(19) 0.29105(10) 0.13842(12) 0.1348(9) Uani 1 1 d . . . . .
C38 C 0.12350(17) 0.41549(8) 0.28120(13) 0.0375(5) Uani 1 1 d . . . . .
H38 H 0.126809 0.415765 0.335529 0.045 Uiso 1 1 calc R . . . .
C25 C 1.04386(18) 0.44926(8) 0.58875(12) 0.0393(5) Uani 1 1 d . . . . .
C23 C 0.97152(17) 0.40352(8) 0.46380(12) 0.0389(5) Uani 1 1 d . . . . .
H23 H 0.982184 0.393759 0.414094 0.047 Uiso 1 1 calc R . . . .
C40 C 0.25992(18) 0.33574(8) 0.44764(12) 0.0390(5) Uani 1 1 d . . . . .
H40 H 0.291111 0.371356 0.461841 0.047 Uiso 1 1 calc R . . . .
C46 C 0.6493(2) 0.09414(8) 0.32772(11) 0.0402(5) Uani 1 1 d . . . . .
C24 C 1.06099(18) 0.43525(9) 0.51675(13) 0.0424(5) Uani 1 1 d . . . . .
H24 H 1.130956 0.446572 0.502943 0.051 Uiso 1 1 calc R . . . .
C5 C 0.5062(2) 0.15056(8) 0.63615(12) 0.0417(5) Uani 1 1 d . . . . .
H5 H 0.499548 0.142248 0.687327 0.050 Uiso 1 1 calc R . . . .
C3 C 0.5116(2) 0.11799(8) 0.50354(12) 0.0411(5) Uani 1 1 d . . . . .
H3 H 0.509655 0.088473 0.468226 0.049 Uiso 1 1 calc R . . . .
C34 C 0.19643(19) 0.38248(9) 0.17298(12) 0.0435(5) Uani 1 1 d . . . . .
H34 H 0.249633 0.360295 0.153866 0.052 Uiso 1 1 calc R . . . .
C27 C 0.85600(19) 0.40031(9) 0.55913(12) 0.0454(5) Uani 1 1 d . . . . .
H27 H 0.788216 0.387857 0.574597 0.054 Uiso 1 1 calc R . . . .
C26 C 0.94364(19) 0.43246(10) 0.61174(13) 0.0478(6) Uani 1 1 d . . . . .
H26 H 0.934376 0.442402 0.661741 0.057 Uiso 1 1 calc R . . . .
C54 C 0.30741(19) 0.11927(9) 0.30251(12) 0.0445(5) Uani 1 1 d . . . . .
H54 H 0.324629 0.149943 0.341534 0.053 Uiso 1 1 calc R . . . .
C41 C 0.2173(2) 0.30466(10) 0.50239(14) 0.0504(6) Uani 1 1 d . . . . .
H41 H 0.218133 0.319370 0.552309 0.061 Uiso 1 1 calc R . . . .
C47 C 0.6479(3) 0.03681(9) 0.31345(13) 0.0537(6) Uani 1 1 d . . . . .
H47 H 0.720943 0.018522 0.315524 0.064 Uiso 1 1 calc R . . . .
C4 C 0.5019(2) 0.10828(9) 0.58200(12) 0.0488(6) Uani 1 1 d . . . . .
H4 H 0.492123 0.071764 0.597591 0.059 Uiso 1 1 calc R . . . .
C37 C 0.03710(19) 0.44803(9) 0.22806(14) 0.0462(5) Uani 1 1 d . . . . .
H37 H -0.016945 0.470201 0.246411 0.055 Uiso 1 1 calc R . . . .
C49 C 0.4326(2) 0.03294(9) 0.29314(12) 0.0513(6) Uani 1 1 d . . . . .
H49 H 0.360735 0.012105 0.280654 0.062 Uiso 1 1 calc R . . . .
C48 C 0.5413(3) 0.00687(9) 0.29646(13) 0.0595(7) Uani 1 1 d . . . . .
H48 H 0.542654 -0.031361 0.287118 0.071 Uiso 1 1 calc R . . . .
C51 C 0.7660(2) 0.12769(10) 0.34559(14) 0.0530(6) Uani 1 1 d . . . . .
H51 H 0.742782 0.166637 0.331826 0.064 Uiso 1 1 calc R . . . .
C36 C 0.0326(2) 0.44702(9) 0.14851(14) 0.0516(6) Uani 1 1 d . . . . .
C17 C 0.7767(2) 0.37308(11) 0.28346(13) 0.0522(6) Uani 1 1 d . . . . .
H17 H 0.745133 0.408496 0.287532 0.063 Uiso 1 1 calc R . . . .
C35 C 0.1100(2) 0.41484(10) 0.11922(14) 0.0569(6) Uani 1 1 d . . . . .
H35 H 0.105009 0.414601 0.064639 0.068 Uiso 1 1 calc R . . . .
C42 C 0.1745(2) 0.25234(10) 0.48118(17) 0.0580(7) Uani 1 1 d . . . . .
C56 C 0.2588(2) 0.14542(10) 0.21890(13) 0.0560(6) Uani 1 1 d . . . . .
H56A H 0.314859 0.173556 0.211306 0.084 Uiso 1 1 calc GR . . . .
H56B H 0.180286 0.162092 0.214428 0.084 Uiso 1 1 calc GR . . . .
H56C H 0.250722 0.116992 0.178628 0.084 Uiso 1 1 calc GR . . . .
C44 C 0.2122(2) 0.26152(9) 0.35463(15) 0.0535(6) Uani 1 1 d . . . . .
H44 H 0.210042 0.246406 0.304719 0.064 Uiso 1 1 calc R . . . .
C18 C 0.8047(2) 0.35808(14) 0.21293(16) 0.0679(8) Uani 1 1 d . . . . .
H18 H 0.792363 0.383005 0.170208 0.081 Uiso 1 1 calc R . . . .
C21 C 0.8421(2) 0.28494(11) 0.34000(18) 0.0685(8) Uani 1 1 d . . . . .
H21 H 0.855849 0.259696 0.382410 0.082 Uiso 1 1 calc R . . . .
C43 C 0.1705(3) 0.22996(10) 0.40859(18) 0.0726(8) Uani 1 1 d . . . . .
H43 H 0.140313 0.194062 0.395359 0.087 Uiso 1 1 calc R . . . .
C55 C 0.2114(2) 0.08180(11) 0.32354(16) 0.0701(8) Uani 1 1 d . . . . .
H55A H 0.188732 0.052457 0.284440 0.105 Uiso 1 1 calc GR . . . .
H55B H 0.140481 0.103610 0.323533 0.105 Uiso 1 1 calc GR . . . .
H55C H 0.244891 0.065803 0.375846 0.105 Uiso 1 1 calc GR . . . .
C19 C 0.8500(3) 0.30684(17) 0.2078(2) 0.0824(10) Uani 1 1 d . . . . .
C53 C 0.8488(3) 0.10967(12) 0.2939(2) 0.0871(10) Uani 1 1 d . . . . .
H53A H 0.875939 0.072016 0.307236 0.131 Uiso 1 1 calc GR . . . .
H53B H 0.918387 0.134075 0.303720 0.131 Uiso 1 1 calc GR . . . .
H53C H 0.804074 0.111575 0.238157 0.131 Uiso 1 1 calc GR . . . .
C52 C 0.8324(3) 0.12625(14) 0.43463(18) 0.0902(10) Uani 1 1 d . . . . .
H52A H 0.779853 0.140801 0.464893 0.135 Uiso 1 1 calc GR . . . .
H52B H 0.905183 0.148639 0.444513 0.135 Uiso 1 1 calc GR . . . .
H52C H 0.854247 0.088411 0.450760 0.135 Uiso 1 1 calc GR . . . .
C20 C 0.8702(3) 0.26991(14) 0.2688(2) 0.0949(11) Uani 1 1 d . . . . .
H20 H 0.902481 0.234815 0.263730 0.114 Uiso 1 1 calc R . . . .


_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 C25 1.366(2) . ?
O1 N3 1.2249(19) . ?
N2 C13 1.411(2) . ?
N2 C12 1.280(2) . ?
O2 N3 1.2278(19) . ?
N1 C1 1.273(2) . ?
N1 C45 1.430(2) . ?
F3 C36 1.360(2) . ?
N3 C29 1.466(2) . ?
F4 C42 1.361(2) . ?
C13 C31 1.407(2) . ?
C13 C14 1.414(2) . ?
C1 C12 1.522(2) . ?
C1 C2 1.484(2) . ?
C10 C12 1.481(2) . ?
C10 C11 1.417(2) . ?
C10 C9 1.372(2) . ?
C31 C32 1.526(2) . ?
C31 C30 1.386(2) . ?
C11 C2 1.411(2) . ?
C11 C6 1.404(2) . ?
C14 C28 1.388(2) . ?
C14 C15 1.524(2) . ?
C32 H32 0.9800 . ?
C32 C33 1.524(2) . ?
C32 C39 1.526(2) . ?
C29 C30 1.380(2) . ?
C29 C28 1.380(2) . ?
C30 H30 0.9300 . ?
C45 C50 1.398(3) . ?
C45 C46 1.400(3) . ?
C2 C3 1.371(2) . ?
C28 H28 0.9300 . ?
C33 C38 1.387(3) . ?
C33 C34 1.388(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.412(2) . ?
C39 C40 1.376(3) . ?
C39 C44 1.381(3) . ?
C6 C7 1.414(3) . ?
C6 C5 1.411(3) . ?
C15 H15 0.9800 . ?
C15 C22 1.532(3) . ?
C15 C16 1.525(3) . ?
C22 C23 1.376(3) . ?
C22 C27 1.392(3) . ?
C50 C54 1.511(3) . ?
C50 C49 1.394(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.372(3) . ?
C7 H7 0.9300 . ?
C16 C17 1.379(3) . ?
C16 C21 1.376(3) . ?
F2 C19 1.363(3) . ?
C38 H38 0.9300 . ?
C38 C37 1.386(3) . ?
C25 C24 1.354(3) . ?
C25 C26 1.364(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.393(3) . ?
C40 H40 0.9300 . ?
C40 C41 1.390(3) . ?
C46 C47 1.393(3) . ?
C46 C51 1.508(3) . ?
C24 H24 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.371(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.410(3) . ?
C34 H34 0.9300 . ?
C34 C35 1.389(3) . ?
C27 H27 0.9300 . ?
C27 C26 1.384(3) . ?
C26 H26 0.9300 . ?
C54 H54 0.9800 . ?
C54 C56 1.533(3) . ?
C54 C55 1.530(3) . ?
C41 H41 0.9300 . ?
C41 C42 1.357(3) . ?
C47 H47 0.9300 . ?
C47 C48 1.367(3) . ?
C4 H4 0.9300 . ?
C37 H37 0.9300 . ?
C37 C36 1.363(3) . ?
C49 H49 0.9300 . ?
C49 C48 1.370(3) . ?
C48 H48 0.9300 . ?
C51 H51 0.9800 . ?
C51 C53 1.526(3) . ?
C51 C52 1.519(3) . ?
C36 C35 1.366(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.389(3) . ?
C35 H35 0.9300 . ?
C42 C43 1.354(4) . ?
C56 H56A 0.9600 . ?
C56 H56B 0.9600 . ?
C56 H56C 0.9600 . ?
C44 H44 0.9300 . ?
C44 C43 1.381(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.342(4) . ?
C21 H21 0.9300 . ?
C21 C20 1.400(4) . ?
C43 H43 0.9300 . ?
C55 H55A 0.9600 . ?
C55 H55B 0.9600 . ?
C55 H55C 0.9600 . ?
C19 C20 1.348(4) . ?
C53 H53A 0.9600 . ?
C53 H53B 0.9600 . ?
C53 H53C 0.9600 . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?
C20 H20 0.9300 . ?

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
C12 N2 C13 120.97(14) . . ?
C1 N1 C45 119.93(14) . . ?
O1 N3 O2 123.35(16) . . ?
O1 N3 C29 118.28(15) . . ?
O2 N3 C29 118.37(16) . . ?
N2 C13 C14 120.45(15) . . ?
C31 C13 N2 117.81(15) . . ?
C31 C13 C14 121.52(15) . . ?
N1 C1 C12 121.17(15) . . ?
N1 C1 C2 132.46(16) . . ?
C2 C1 C12 106.36(14) . . ?
C11 C10 C12 106.44(14) . . ?
C9 C10 C12 134.69(16) . . ?
C9 C10 C11 118.86(15) . . ?
N2 C12 C1 121.04(15) . . ?
N2 C12 C10 132.23(16) . . ?
C10 C12 C1 106.68(14) . . ?
C13 C31 C32 119.25(15) . . ?
C30 C31 C13 118.46(16) . . ?
C30 C31 C32 122.29(16) . . ?
C2 C11 C10 113.70(15) . . ?
C6 C11 C10 122.95(16) . . ?
C6 C11 C2 123.35(16) . . ?
C13 C14 C15 119.84(15) . . ?
C28 C14 C13 118.12(16) . . ?
C28 C14 C15 122.00(16) . . ?
C31 C32 H32 105.9 . . ?
C33 C32 C31 112.87(14) . . ?
C33 C32 H32 105.9 . . ?
C33 C32 C39 113.25(14) . . ?
C39 C32 C31 112.27(14) . . ?
C39 C32 H32 105.9 . . ?
C30 C29 N3 118.55(16) . . ?
C28 C29 N3 118.97(16) . . ?
C28 C29 C30 122.46(16) . . ?
C31 C30 H30 120.2 . . ?
C29 C30 C31 119.54(17) . . ?
C29 C30 H30 120.2 . . ?
C50 C45 N1 120.51(17) . . ?
C50 C45 C46 122.31(17) . . ?
C46 C45 N1 117.00(17) . . ?
C11 C2 C1 106.66(15) . . ?
C3 C2 C1 134.29(16) . . ?
C3 C2 C11 119.04(16) . . ?
C14 C28 H28 120.2 . . ?
C29 C28 C14 119.69(17) . . ?
C29 C28 H28 120.2 . . ?
C38 C33 C32 122.42(17) . . ?
C38 C33 C34 117.95(18) . . ?
C34 C33 C32 119.62(17) . . ?
C10 C9 H9 120.5 . . ?
C10 C9 C8 118.90(17) . . ?
C8 C9 H9 120.5 . . ?
C40 C39 C32 122.79(16) . . ?
C40 C39 C44 117.52(18) . . ?
C44 C39 C32 119.66(17) . . ?
C11 C6 C7 116.48(17) . . ?
C11 C6 C5 116.03(17) . . ?
C5 C6 C7 127.48(17) . . ?
C14 C15 H15 106.7 . . ?
C14 C15 C22 112.45(15) . . ?
C14 C15 C16 110.04(15) . . ?
C22 C15 H15 106.7 . . ?
C16 C15 H15 106.7 . . ?
C16 C15 C22 113.70(15) . . ?
C23 C22 C15 122.81(18) . . ?
C23 C22 C27 117.90(18) . . ?
C27 C22 C15 119.28(17) . . ?
C45 C50 C54 121.04(17) . . ?
C49 C50 C45 117.2(2) . . ?
C49 C50 C54 121.7(2) . . ?
C9 C8 H8 118.9 . . ?
C7 C8 C9 122.24(17) . . ?
C7 C8 H8 118.9 . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.52(17) . . ?
C8 C7 H7 119.7 . . ?
C17 C16 C15 121.63(19) . . ?
C21 C16 C15 120.6(2) . . ?
C21 C16 C17 117.8(2) . . ?
C33 C38 H38 119.5 . . ?
C37 C38 C33 121.0(2) . . ?
C37 C38 H38 119.5 . . ?
C24 C25 F1 118.93(18) . . ?
C24 C25 C26 122.37(19) . . ?
C26 C25 F1 118.68(19) . . ?
C22 C23 H23 119.3 . . ?
C22 C23 C24 121.4(2) . . ?
C24 C23 H23 119.3 . . ?
C39 C40 H40 119.2 . . ?
C39 C40 C41 121.5(2) . . ?
C41 C40 H40 119.2 . . ?
C45 C46 C51 120.83(18) . . ?
C47 C46 C45 117.3(2) . . ?
C47 C46 C51 121.8(2) . . ?
C25 C24 C23 118.54(19) . . ?
C25 C24 H24 120.7 . . ?
C23 C24 H24 120.7 . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.64(18) . . ?
C4 C5 H5 119.7 . . ?
C2 C3 H3 120.8 . . ?
C2 C3 C4 118.37(18) . . ?
C4 C3 H3 120.8 . . ?
C33 C34 H34 119.3 . . ?
C33 C34 C35 121.4(2) . . ?
C35 C34 H34 119.3 . . ?
C22 C27 H27 119.5 . . ?
C26 C27 C22 121.08(19) . . ?
C26 C27 H27 119.5 . . ?
C25 C26 C27 118.7(2) . . ?
C25 C26 H26 120.7 . . ?
C27 C26 H26 120.7 . . ?
C50 C54 H54 107.3 . . ?
C50 C54 C56 109.62(17) . . ?
C50 C54 C55 113.63(19) . . ?
C56 C54 H54 107.3 . . ?
C55 C54 H54 107.3 . . ?
C55 C54 C56 111.51(19) . . ?
C40 C41 H41 120.8 . . ?
C42 C41 C40 118.4(2) . . ?
C42 C41 H41 120.8 . . ?
C46 C47 H47 119.3 . . ?
C48 C47 C46 121.4(2) . . ?
C48 C47 H47 119.3 . . ?
C5 C4 C3 122.55(18) . . ?
C5 C4 H4 118.7 . . ?
C3 C4 H4 118.7 . . ?
C38 C37 H37 120.5 . . ?
C36 C37 C38 119.0(2) . . ?
C36 C37 H37 120.5 . . ?
C50 C49 H49 119.3 . . ?
C48 C49 C50 121.4(2) . . ?
C48 C49 H49 119.3 . . ?
C47 C48 C49 120.3(2) . . ?
C47 C48 H48 119.8 . . ?
C49 C48 H48 119.8 . . ?
C46 C51 H51 107.1 . . ?
C46 C51 C53 112.1(2) . . ?
C46 C51 C52 111.2(2) . . ?
C53 C51 H51 107.1 . . ?
C52 C51 H51 107.1 . . ?
C52 C51 C53 111.9(2) . . ?
F3 C36 C37 118.7(2) . . ?
F3 C36 C35 119.1(2) . . ?
C37 C36 C35 122.2(2) . . ?
C16 C17 H17 119.2 . . ?
C16 C17 C18 121.7(2) . . ?
C18 C17 H17 119.2 . . ?
C34 C35 H35 120.8 . . ?
C36 C35 C34 118.3(2) . . ?
C36 C35 H35 120.8 . . ?
C41 C42 F4 118.9(2) . . ?
C43 C42 F4 118.8(2) . . ?
C43 C42 C41 122.3(2) . . ?
C54 C56 H56A 109.5 . . ?
C54 C56 H56B 109.5 . . ?
C54 C56 H56C 109.5 . . ?
H56A C56 H56B 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
C39 C44 H44 119.2 . . ?
C43 C44 C39 121.7(2) . . ?
C43 C44 H44 119.2 . . ?
C17 C18 H18 120.7 . . ?
C19 C18 C17 118.6(3) . . ?
C19 C18 H18 120.7 . . ?
C16 C21 H21 119.8 . . ?
C16 C21 C20 120.4(3) . . ?
C20 C21 H21 119.8 . . ?
C42 C43 C44 118.6(2) . . ?
C42 C43 H43 120.7 . . ?
C44 C43 H43 120.7 . . ?
C54 C55 H55A 109.5 . . ?
C54 C55 H55B 109.5 . . ?
C54 C55 H55C 109.5 . . ?
H55A C55 H55B 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?
C18 C19 F2 119.3(4) . . ?
C18 C19 C20 122.2(3) . . ?
C20 C19 F2 118.4(3) . . ?
C51 C53 H53A 109.5 . . ?
C51 C53 H53B 109.5 . . ?
C51 C53 H53C 109.5 . . ?
H53A C53 H53B 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52B 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C21 C20 H20 120.4 . . ?
C19 C20 C21 119.3(3) . . ?
C19 C20 H20 120.4 . . ?

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

data_Ni3
_database_code_depnum_ccdc_archive 'CCDC 1877304'
_audit_update_record             
;
2018-11-06 deposited with the CCDC.
2018-12-26 downloaded from the CCDC.
;
_audit_creation_date             2017-12-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C56 H45 Br2 F4 N3 Ni O3'
_chemical_formula_sum            'C56 H45 Br2 F4 N3 Ni O3'
_chemical_formula_weight         1102.48
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.3027(3)
_cell_length_b                   32.3842(7)
_cell_length_c                   15.9132(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.872(3)
_cell_angle_gamma                90
_cell_volume                     5511.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    21434
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      30.1940
_cell_measurement_theta_min      1.8340
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.858
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62283
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2240
_exptl_crystal_size_max          0.308
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.132
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1041
_diffrn_reflns_av_unetI/netI     0.1026
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       47
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            92431
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.560
_diffrn_reflns_theta_min         1.491
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9557
_reflns_number_total             17353
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         1.239
_refine_diff_density_min         -0.684
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     627
_refine_ls_number_reflns         17353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1413
_refine_ls_R_factor_gt           0.0700
_refine_ls_restrained_S_all      1.038
_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)+(0.0835P)²+0.0075P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1595
_refine_ls_wR_factor_ref         0.1849
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Rotating group:
 O3(H3A,H3B)
2.b Ternary CH refined with riding coordinates:
 C38(H38), C15(H15), C47(H47), C54(H54)
2.c Aromatic/amide H refined with riding coordinates:
 C30(H30), C43(H43), C3(H3), C33(H33), C44(H44), C9(H9), C28(H28), C34(H34),
 C40(H40), C41(H41), C50(H50), C37(H37), C5(H5), C52(H52), C8(H8), C51(H51),
 C23(H23), C17(H17), C4(H4), C21(H21), C36(H36), C27(H27), C18(H18), C20(H20),
 C26(H26), C7(H7), C24(H24)
2.d Idealised Me refined as rotating group:
 C48(H48A,H48B,H48C), C56(H56A,H56B,H56C), C49(H49A,H49B,H49C), C55(H55A,H55B,
 H55C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
Br2 Br 0.79968(4) 0.06210(2) 0.92275(3) 0.03651(12) Uani 1 1 d . . . . .
Ni1 Ni 1.01762(4) 0.07494(2) 0.94572(3) 0.02818(12) Uani 1 1 d . . . . .
Br1 Br 1.10294(4) 0.06966(2) 1.10642(3) 0.04587(13) Uani 1 1 d . . . . .
N2 N 1.0142(2) 0.08237(8) 0.81259(19) 0.0239(6) Uani 1 1 d . . . . .
F4 F 1.5988(2) -0.07924(7) 0.96953(16) 0.0483(6) Uani 1 1 d . . . . .
N1 N 1.0260(2) 0.13987(8) 0.93758(19) 0.0247(6) Uani 1 1 d . . . . .
N3 N 0.9966(3) -0.04316(9) 0.5650(2) 0.0346(7) Uani 1 1 d . . . . .
C30 C 1.1163(3) -0.00050(10) 0.6905(2) 0.0270(8) Uani 1 1 d . . . . .
H30 H 1.188415 -0.014265 0.690263 0.032 Uiso 1 1 calc R . . . .
C38 C 1.2459(3) 0.04523(10) 0.8189(2) 0.0244(7) Uani 1 1 d . . . . .
H38 H 1.225941 0.054568 0.871336 0.029 Uiso 1 1 calc R . . . .
C12 C 1.0247(3) 0.12033(10) 0.7918(2) 0.0259(7) Uani 1 1 d . . . . .
C1 C 1.0300(3) 0.15225(10) 0.8631(2) 0.0250(7) Uani 1 1 d . . . . .
C11 C 1.0472(3) 0.18474(11) 0.7377(2) 0.0291(8) Uani 1 1 d . . . . .
C31 C 1.1223(3) 0.03091(10) 0.7512(2) 0.0263(7) Uani 1 1 d . . . . .
C2 C 1.0416(3) 0.19296(11) 0.8242(2) 0.0299(8) Uani 1 1 d . . . . .
C43 C 1.3907(4) -0.05719(12) 0.9188(3) 0.0375(9) Uani 1 1 d . . . . .
H43 H 1.366070 -0.081659 0.938848 0.045 Uiso 1 1 calc R . . . .
C32 C 1.2968(3) 0.08280(11) 0.7838(3) 0.0285(8) Uani 1 1 d . . . . .
C3 C 1.0540(3) 0.23284(10) 0.8547(3) 0.0334(9) Uani 1 1 d . . . . .
H3 H 1.050750 0.238998 0.910998 0.040 Uiso 1 1 calc R . . . .
C39 C 1.3414(3) 0.01005(10) 0.8502(2) 0.0253(7) Uani 1 1 d . . . . .
C33 C 1.3254(3) 0.11841(11) 0.8342(3) 0.0325(8) Uani 1 1 d . . . . .
H33 H 1.316226 0.118860 0.890177 0.039 Uiso 1 1 calc R . . . .
C44 C 1.3039(3) -0.02676(11) 0.8784(3) 0.0323(8) Uani 1 1 d . . . . .
H44 H 1.219625 -0.031178 0.870249 0.039 Uiso 1 1 calc R . . . .
C15 C 0.7731(3) 0.05947(11) 0.6919(3) 0.0304(8) Uani 1 1 d . . . . .
H15 H 0.787251 0.067551 0.753692 0.036 Uiso 1 1 calc R . . . .
C45 C 1.0295(3) 0.17044(10) 1.0054(2) 0.0293(8) Uani 1 1 d . . . . .
C9 C 1.0421(4) 0.13036(11) 0.6334(2) 0.0354(9) Uani 1 1 d . . . . .
H9 H 1.035650 0.102681 0.616923 0.043 Uiso 1 1 calc R . . . .
C13 C 1.0097(3) 0.05058(10) 0.7489(2) 0.0233(7) Uani 1 1 d . . . . .
O2 O 0.9021(3) -0.04712(9) 0.5022(2) 0.0527(8) Uani 1 1 d . . . . .
C6 C 1.0647(4) 0.21528(11) 0.6813(3) 0.0369(9) Uani 1 1 d . . . . .
C29 C 1.0019(3) -0.01090(10) 0.6307(2) 0.0285(8) Uani 1 1 d . . . . .
C48 C 1.3360(4) 0.18998(13) 1.0229(3) 0.0447(10) Uani 1 1 d . . . . .
H48A H 1.284403 0.195794 0.963083 0.067 Uiso 1 1 calc GR . . . .
H48B H 1.412157 0.177085 1.022151 0.067 Uiso 1 1 calc GR . . . .
H48C H 1.355215 0.215283 1.055948 0.067 Uiso 1 1 calc GR . . . .
C10 C 1.0364(3) 0.14200(10) 0.7145(2) 0.0280(8) Uani 1 1 d . . . . .
C47 C 1.2667(3) 0.16113(11) 1.0663(3) 0.0359(9) Uani 1 1 d . . . . .
H47 H 1.245848 0.135973 1.030265 0.043 Uiso 1 1 calc R . . . .
C28 C 0.8926(3) 0.00733(10) 0.6296(2) 0.0300(8) Uani 1 1 d . . . . .
H28 H 0.817621 -0.000975 0.588043 0.036 Uiso 1 1 calc R . . . .
C34 C 1.3676(4) 0.15366(12) 0.8025(3) 0.0424(10) Uani 1 1 d . . . . .
H34 H 1.383936 0.177883 0.835651 0.051 Uiso 1 1 calc R . . . .
C40 C 1.4662(3) 0.01540(11) 0.8605(3) 0.0333(9) Uani 1 1 d . . . . .
H40 H 1.492494 0.039729 0.841014 0.040 Uiso 1 1 calc R . . . .
C14 C 0.8927(3) 0.03829(10) 0.6901(2) 0.0277(8) Uani 1 1 d . . . . .
C22 C 0.6607(3) 0.02956(13) 0.6668(3) 0.0396(10) Uani 1 1 d . . . . .
F3 F 1.4240(3) 0.18582(8) 0.6894(2) 0.0731(9) Uani 1 1 d . . . . .
C42 C 1.5134(4) -0.04989(11) 0.9280(2) 0.0336(9) Uani 1 1 d . . . . .
C41 C 1.5531(3) -0.01489(12) 0.8995(3) 0.0367(9) Uani 1 1 d . . . . .
H41 H 1.637162 -0.011199 0.905838 0.044 Uiso 1 1 calc R . . . .
O1 O 1.0881(3) -0.06479(11) 0.5759(3) 0.0715(12) Uani 1 1 d . . . . .
C50 C 1.1466(4) 0.20933(12) 1.1315(3) 0.0420(10) Uani 1 1 d . . . . .
H50 H 1.222221 0.216438 1.173854 0.050 Uiso 1 1 calc R . . . .
C37 C 1.3137(4) 0.08195(12) 0.7021(3) 0.0395(10) Uani 1 1 d . . . . .
H37 H 1.295115 0.057957 0.668263 0.047 Uiso 1 1 calc R . . . .
C5 C 1.0781(4) 0.25586(12) 0.7153(3) 0.0455(11) Uani 1 1 d . . . . .
H5 H 1.091390 0.277471 0.680978 0.055 Uiso 1 1 calc R . . . .
C16 C 0.7498(3) 0.09900(12) 0.6384(3) 0.0367(9) Uani 1 1 d . . . . .
C54 C 0.7905(4) 0.17749(13) 0.9392(3) 0.0424(10) Uani 1 1 d . . . . .
H54 H 0.803174 0.153812 0.904689 0.051 Uiso 1 1 calc R . . . .
C35 C 1.3844(4) 0.15166(13) 0.7218(3) 0.0474(11) Uani 1 1 d . . . . .
C52 C 0.9243(4) 0.21819(12) 1.0700(3) 0.0444(10) Uani 1 1 d . . . . .
H52 H 0.851696 0.231343 1.071092 0.053 Uiso 1 1 calc R . . . .
C8 C 1.0577(4) 0.16100(13) 0.5753(3) 0.0475(11) Uani 1 1 d . . . . .
H8 H 1.060159 0.153344 0.519548 0.057 Uiso 1 1 calc R . . . .
C51 C 1.0377(4) 0.22848(12) 1.1333(3) 0.0474(11) Uani 1 1 d . . . . .
H51 H 1.040475 0.248091 1.176567 0.057 Uiso 1 1 calc R . . . .
F1 F 0.7089(4) 0.20900(9) 0.5045(2) 0.0975(12) Uani 1 1 d . . . . .
C53 C 0.9170(4) 0.18887(11) 1.0054(3) 0.0345(9) Uani 1 1 d . . . . .
C23 C 0.5472(4) 0.03881(17) 0.6032(3) 0.0581(14) Uani 1 1 d . . . . .
H23 H 0.538457 0.063092 0.570499 0.070 Uiso 1 1 calc R . . . .
C17 C 0.7254(4) 0.13514(13) 0.6772(3) 0.0469(11) Uani 1 1 d . . . . .
H17 H 0.718405 0.134395 0.733840 0.056 Uiso 1 1 calc R . . . .
C4 C 1.0717(4) 0.26398(12) 0.7993(3) 0.0433(10) Uani 1 1 d . . . . .
H4 H 1.079402 0.291135 0.819396 0.052 Uiso 1 1 calc R . . . .
C46 C 1.1454(3) 0.18024(11) 1.0689(3) 0.0316(8) Uani 1 1 d . . . . .
C21 C 0.7557(4) 0.10031(14) 0.5534(3) 0.0464(11) Uani 1 1 d . . . . .
H21 H 0.769583 0.076021 0.526911 0.056 Uiso 1 1 calc R . . . .
C56 C 0.7366(4) 0.21227(14) 0.8747(3) 0.0589(13) Uani 1 1 d . . . . .
H56A H 0.726561 0.236339 0.906940 0.088 Uiso 1 1 calc GR . . . .
H56B H 0.656788 0.204089 0.834355 0.088 Uiso 1 1 calc GR . . . .
H56C H 0.792287 0.218448 0.841865 0.088 Uiso 1 1 calc GR . . . .
C36 C 1.3583(4) 0.11643(14) 0.6688(3) 0.0531(12) Uani 1 1 d . . . . .
H36 H 1.370048 0.115868 0.613595 0.064 Uiso 1 1 calc R . . . .
C19 C 0.7197(5) 0.17271(16) 0.5478(4) 0.0675(15) Uani 1 1 d . . . . .
C27 C 0.6705(4) -0.00702(14) 0.7127(3) 0.0499(12) Uani 1 1 d . . . . .
H27 H 0.746523 -0.013932 0.754856 0.060 Uiso 1 1 calc R . . . .
C49 C 1.3529(4) 0.14886(13) 1.1595(3) 0.0533(12) Uani 1 1 d . . . . .
H49A H 1.424231 0.134253 1.154515 0.080 Uiso 1 1 calc GR . . . .
H49B H 1.307952 0.131427 1.187505 0.080 Uiso 1 1 calc GR . . . .
H49C H 1.380301 0.173273 1.194700 0.080 Uiso 1 1 calc GR . . . .
C18 C 0.7114(5) 0.17245(14) 0.6313(4) 0.0626(14) Uani 1 1 d . . . . .
H18 H 0.696578 0.196784 0.657323 0.075 Uiso 1 1 calc R . . . .
C20 C 0.7411(5) 0.13742(15) 0.5061(3) 0.0612(14) Uani 1 1 d . . . . .
H20 H 0.745749 0.138299 0.448783 0.073 Uiso 1 1 calc R . . . .
C55 C 0.6992(4) 0.16391(16) 0.9882(4) 0.0614(14) Uani 1 1 d . . . . .
H55A H 0.739932 0.144367 1.033730 0.092 Uiso 1 1 calc GR . . . .
H55B H 0.626821 0.151345 0.946717 0.092 Uiso 1 1 calc GR . . . .
H55C H 0.674190 0.187589 1.014619 0.092 Uiso 1 1 calc GR . . . .
C26 C 0.5703(5) -0.03377(17) 0.6980(4) 0.0684(16) Uani 1 1 d . . . . .
H26 H 0.578082 -0.058564 0.728762 0.082 Uiso 1 1 calc R . . . .
F2 F 0.3597(3) -0.04791(13) 0.6229(3) 0.1234(17) Uani 1 1 d . . . . .
C7 C 1.0696(4) 0.20252(13) 0.5992(3) 0.0480(11) Uani 1 1 d . . . . .
H7 H 1.081107 0.222003 0.559609 0.058 Uiso 1 1 calc R . . . .
C25 C 0.4592(5) -0.0223(2) 0.6362(5) 0.085(2) Uani 1 1 d . . . . .
C24 C 0.4463(5) 0.0120(2) 0.5878(4) 0.082(2) Uani 1 1 d . . . . .
H24 H 0.370656 0.017881 0.544303 0.098 Uiso 1 1 calc R . . . .
O3 O 1.0688(2) 0.01427(7) 0.93490(18) 0.0341(6) Uani 1 1 d . . . . .
H3A H 1.106546 0.012808 0.896611 0.051 Uiso 1 1 d GR . . . .
H3B H 1.003453 -0.000322 0.913258 0.051 Uiso 1 1 d GR . . . .


_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
Br2 Ni1 2.4067(6) . ?
Ni1 Br1 2.4297(6) . ?
Ni1 N2 2.120(3) . ?
Ni1 N1 2.111(3) . ?
Ni1 O3 2.071(2) . ?
N2 C12 1.288(4) . ?
N2 C13 1.434(4) . ?
F4 C42 1.364(4) . ?
N1 C1 1.265(4) . ?
N1 C45 1.456(4) . ?
N3 O2 1.209(4) . ?
N3 C29 1.466(4) . ?
N3 O1 1.214(4) . ?
C30 C31 1.389(5) . ?
C30 C29 1.377(5) . ?
C38 C31 1.534(5) . ?
C38 C32 1.527(5) . ?
C38 C39 1.537(4) . ?
C12 C1 1.522(5) . ?
C12 C10 1.459(5) . ?
C1 C2 1.481(5) . ?
C11 C2 1.423(5) . ?
C11 C6 1.392(5) . ?
C11 C10 1.427(5) . ?
C31 C13 1.413(5) . ?
C2 C3 1.371(5) . ?
C43 C44 1.392(5) . ?
C43 C42 1.367(5) . ?
C32 C33 1.381(5) . ?
C32 C37 1.375(6) . ?
C3 C4 1.396(5) . ?
C39 C44 1.387(5) . ?
C39 C40 1.378(5) . ?
C33 C34 1.393(5) . ?
C15 C14 1.524(5) . ?
C15 C22 1.543(5) . ?
C15 C16 1.512(5) . ?
C45 C53 1.404(5) . ?
C45 C46 1.407(5) . ?
C9 C10 1.366(5) . ?
C9 C8 1.406(5) . ?
C13 C14 1.407(5) . ?
C6 C5 1.411(5) . ?
C6 C7 1.388(6) . ?
C29 C28 1.364(5) . ?
C48 C47 1.521(6) . ?
C47 C46 1.518(5) . ?
C47 C49 1.541(6) . ?
C28 C14 1.390(5) . ?
C34 C35 1.359(6) . ?
C40 C41 1.385(5) . ?
C22 C23 1.386(5) . ?
C22 C27 1.378(6) . ?
F3 C35 1.356(5) . ?
C42 C41 1.351(5) . ?
C50 C51 1.387(6) . ?
C50 C46 1.368(5) . ?
C37 C36 1.398(6) . ?
C5 C4 1.386(6) . ?
C16 C17 1.392(5) . ?
C16 C21 1.376(6) . ?
C54 C53 1.522(5) . ?
C54 C56 1.513(6) . ?
C54 C55 1.545(6) . ?
C35 C36 1.392(6) . ?
C52 C51 1.391(6) . ?
C52 C53 1.382(5) . ?
C8 C7 1.392(6) . ?
F1 C19 1.348(6) . ?
C23 C24 1.392(7) . ?
C17 C18 1.394(6) . ?
C21 C20 1.400(6) . ?
C19 C18 1.362(8) . ?
C19 C20 1.383(7) . ?
C27 C26 1.384(6) . ?
C26 C25 1.371(9) . ?
F2 C25 1.357(6) . ?
C25 C24 1.332(9) . ?

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
Br2 Ni1 Br1 100.72(2) . . ?
N2 Ni1 Br2 100.41(7) . . ?
N2 Ni1 Br1 158.83(8) . . ?
N1 Ni1 Br2 103.12(8) . . ?
N1 Ni1 Br1 97.14(8) . . ?
N1 Ni1 N2 79.17(11) . . ?
O3 Ni1 Br2 97.08(7) . . ?
O3 Ni1 Br1 89.68(8) . . ?
O3 Ni1 N2 86.56(10) . . ?
O3 Ni1 N1 157.01(11) . . ?
C12 N2 Ni1 113.0(2) . . ?
C12 N2 C13 119.2(3) . . ?
C13 N2 Ni1 127.6(2) . . ?
C1 N1 Ni1 112.9(2) . . ?
C1 N1 C45 118.6(3) . . ?
C45 N1 Ni1 128.5(2) . . ?
O2 N3 C29 119.1(3) . . ?
O2 N3 O1 122.7(3) . . ?
O1 N3 C29 118.2(3) . . ?
C29 C30 C31 118.9(3) . . ?
C31 C38 C39 112.8(3) . . ?
C32 C38 C31 110.5(3) . . ?
C32 C38 C39 113.6(3) . . ?
N2 C12 C1 116.2(3) . . ?
N2 C12 C10 135.8(3) . . ?
C10 C12 C1 108.0(3) . . ?
N1 C1 C12 118.6(3) . . ?
N1 C1 C2 135.1(3) . . ?
C2 C1 C12 106.3(3) . . ?
C2 C11 C10 113.9(3) . . ?
C6 C11 C2 123.4(3) . . ?
C6 C11 C10 122.7(3) . . ?
C30 C31 C38 122.5(3) . . ?
C30 C31 C13 118.1(3) . . ?
C13 C31 C38 119.3(3) . . ?
C11 C2 C1 106.0(3) . . ?
C3 C2 C1 134.7(4) . . ?
C3 C2 C11 119.2(3) . . ?
C42 C43 C44 117.8(4) . . ?
C33 C32 C38 119.9(3) . . ?
C37 C32 C38 120.9(3) . . ?
C37 C32 C33 119.2(4) . . ?
C2 C3 C4 118.4(4) . . ?
C44 C39 C38 119.1(3) . . ?
C40 C39 C38 122.0(3) . . ?
C40 C39 C44 118.5(3) . . ?
C32 C33 C34 121.2(4) . . ?
C39 C44 C43 121.0(3) . . ?
C14 C15 C22 111.9(3) . . ?
C16 C15 C14 111.4(3) . . ?
C16 C15 C22 114.0(3) . . ?
C53 C45 N1 118.8(3) . . ?
C53 C45 C46 122.4(3) . . ?
C46 C45 N1 118.8(3) . . ?
C10 C9 C8 118.7(4) . . ?
C31 C13 N2 118.7(3) . . ?
C14 C13 N2 118.9(3) . . ?
C14 C13 C31 122.3(3) . . ?
C11 C6 C5 115.7(4) . . ?
C7 C6 C11 116.9(4) . . ?
C7 C6 C5 127.4(4) . . ?
C30 C29 N3 118.7(3) . . ?
C28 C29 N3 118.1(3) . . ?
C28 C29 C30 123.2(3) . . ?
C11 C10 C12 105.8(3) . . ?
C9 C10 C12 135.1(3) . . ?
C9 C10 C11 119.1(3) . . ?
C48 C47 C49 109.7(3) . . ?
C46 C47 C48 111.4(3) . . ?
C46 C47 C49 112.0(4) . . ?
C29 C28 C14 120.3(3) . . ?
C35 C34 C33 118.1(4) . . ?
C39 C40 C41 121.0(4) . . ?
C13 C14 C15 120.6(3) . . ?
C28 C14 C15 122.3(3) . . ?
C28 C14 C13 117.0(3) . . ?
C23 C22 C15 122.9(4) . . ?
C27 C22 C15 119.0(3) . . ?
C27 C22 C23 118.0(4) . . ?
F4 C42 C43 117.8(3) . . ?
C41 C42 F4 119.2(4) . . ?
C41 C42 C43 123.0(3) . . ?
C42 C41 C40 118.7(4) . . ?
C46 C50 C51 121.5(4) . . ?
C32 C37 C36 121.4(4) . . ?
C4 C5 C6 121.0(4) . . ?
C17 C16 C15 119.1(4) . . ?
C21 C16 C15 121.6(3) . . ?
C21 C16 C17 119.3(4) . . ?
C53 C54 C55 110.5(4) . . ?
C56 C54 C53 111.8(3) . . ?
C56 C54 C55 111.5(4) . . ?
C34 C35 C36 123.0(4) . . ?
F3 C35 C34 118.9(4) . . ?
F3 C35 C36 118.0(4) . . ?
C53 C52 C51 121.5(4) . . ?
C7 C8 C9 121.6(4) . . ?
C50 C51 C52 119.6(4) . . ?
C45 C53 C54 123.0(3) . . ?
C52 C53 C45 117.1(4) . . ?
C52 C53 C54 119.9(4) . . ?
C22 C23 C24 120.4(6) . . ?
C16 C17 C18 120.1(5) . . ?
C5 C4 C3 122.3(4) . . ?
C45 C46 C47 121.8(3) . . ?
C50 C46 C45 117.8(4) . . ?
C50 C46 C47 120.3(3) . . ?
C16 C21 C20 121.4(4) . . ?
C35 C36 C37 117.2(4) . . ?
F1 C19 C18 118.8(5) . . ?
F1 C19 C20 118.4(5) . . ?
C18 C19 C20 122.8(5) . . ?
C22 C27 C26 121.8(5) . . ?
C19 C18 C17 119.0(4) . . ?
C19 C20 C21 117.3(5) . . ?
C25 C26 C27 117.5(6) . . ?
C6 C7 C8 121.0(4) . . ?
F2 C25 C26 117.9(7) . . ?
C24 C25 C26 122.9(5) . . ?
C24 C25 F2 119.2(7) . . ?
C25 C24 C23 119.3(5) . . ?

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

data_Ni4
_database_code_depnum_ccdc_archive 'CCDC 1877305'
_audit_update_record             
;
2018-11-06 deposited with the CCDC.
2018-12-26 downloaded from the CCDC.
;
_audit_creation_date             2018-04-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C53 H37 Br2 F4 N3 Ni O2'
_chemical_formula_sum            'C53 H37 Br2 F4 N3 Ni O2'
_chemical_formula_weight         1042.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   14.652(3)
_cell_length_b                   32.546(7)
_cell_length_c                   10.810(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.61(3)
_cell_angle_gamma                90
_cell_volume                     5130.0(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13966
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      27.4844
_cell_measurement_theta_min      1.2513
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.991
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83169
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2104
_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.102
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            69720
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.467
_diffrn_reflns_theta_min         1.251
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                10929
_reflns_number_total             11709
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.206
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.211
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     589
_refine_ls_number_reflns         11709
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0772
_refine_ls_restrained_S_all      1.211
_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)+(0.0437P)²+17.7267P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1558
_refine_ls_wR_factor_ref         0.1614
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15), C32(H32)
2.b Aromatic/amide H refined with riding coordinates:
 C30(H30), C47(H47), C44(H44), C21(H21), C26(H26), C17(H17), C40(H40), C8(H8),
 C7(H7), C28(H28), C9(H9), C3(H3), C23(H23), C35(H35), C41(H41), C38(H38),
 C34(H34), C27(H27), C5(H5), C37(H37), C43(H43), C24(H24), C18(H18), C49(H49),
 C4(H4), C20(H20)
2.c Idealised Me refined as rotating group:
 C52(H52a,H52b,H52c), C51(H51a,H51b,H51c), C53(H53a,H53b,H53c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br2 Br 0.72211(3) 0.04159(2) 0.98255(4) 0.03072(12) Uani 1 1 d . . . A 1
Ni1 Ni 0.71769(4) 0.10799(2) 1.06492(5) 0.02293(13) Uani 1 1 d . . . . .
Br1 Br 0.76405(4) 0.16675(2) 0.96677(5) 0.04254(15) Uani 1 1 d . . . B 1
N2 N 0.7631(2) 0.11195(10) 1.2501(3) 0.0192(7) Uani 1 1 d . . . . .
C1 C 0.5999(3) 0.11247(13) 1.2485(4) 0.0220(8) Uani 1 1 d . . . . .
N1 N 0.5936(2) 0.11155(10) 1.1296(3) 0.0223(7) Uani 1 1 d . . . . .
F1 F 0.5679(2) 0.22394(10) 1.6068(3) 0.0529(9) Uani 1 1 d . . . . .
F2 F 1.0809(3) 0.32252(11) 1.1849(4) 0.0601(10) Uani 1 1 d . . . . .
C12 C 0.6943(3) 0.11218(12) 1.3168(4) 0.0200(8) Uani 1 1 d . . . . .
C45 C 0.5060(3) 0.10871(13) 1.0552(4) 0.0226(9) Uani 1 1 d . . . . .
C13 C 0.8554(3) 0.11440(12) 1.3061(4) 0.0192(8) Uani 1 1 d . . . . .
C15 C 0.8421(3) 0.19307(14) 1.2890(4) 0.0257(9) Uani 1 1 d . . . . .
H15 H 0.807470 0.186993 1.208917 0.031 Uiso 1 1 calc R . . . .
N3 N 1.1314(3) 0.12345(13) 1.4530(4) 0.0296(8) Uani 1 1 d . . . . .
C30 C 0.9965(3) 0.08109(13) 1.3815(4) 0.0223(8) Uani 1 1 d . . . . .
H30 H 1.031357 0.057636 1.400333 0.027 Uiso 1 1 calc R . . . .
F3 F 0.6124(2) -0.01267(12) 1.6329(3) 0.0613(10) Uani 1 1 d . . . . .
C32 C 0.8618(3) 0.03622(13) 1.2958(4) 0.0228(9) Uani 1 1 d . . . . .
H32 H 0.823488 0.040772 1.217439 0.027 Uiso 1 1 calc R . . . .
C31 C 0.9061(3) 0.07775(13) 1.3298(4) 0.0197(8) Uani 1 1 d . . . . .
C2 C 0.5342(3) 0.11326(14) 1.3426(4) 0.0253(9) Uani 1 1 d . . . . .
C29 C 1.0341(3) 0.11986(13) 1.4048(4) 0.0239(9) Uani 1 1 d . . . . .
C47 C 0.3800(3) 0.06822(15) 0.9682(4) 0.0307(10) Uani 1 1 d . . . . .
H47 H 0.348687 0.043345 0.961418 0.037 Uiso 1 1 calc R . . . .
C44 C 0.9247(3) -0.03640(14) 1.3175(4) 0.0265(9) Uani 1 1 d . . . . .
H44 H 0.883596 -0.041739 1.375842 0.032 Uiso 1 1 calc R . . . .
C10 C 0.6840(3) 0.11171(13) 1.4497(4) 0.0228(9) Uani 1 1 d . . . . .
C21 C 0.9095(4) 0.26435(14) 1.3315(5) 0.0330(11) Uani 1 1 d . . . . .
H21 H 0.872270 0.267191 1.395849 0.040 Uiso 1 1 calc R . . . .
C26 C 0.7237(4) 0.21178(15) 1.5836(5) 0.0368(11) Uani 1 1 d . . . . .
H26 H 0.737834 0.212888 1.669332 0.044 Uiso 1 1 calc R . . . .
C14 C 0.8951(3) 0.15363(13) 1.3261(4) 0.0226(8) Uani 1 1 d . . . . .
O1 O 1.1685(3) 0.15688(12) 1.4459(4) 0.0513(11) Uani 1 1 d . . . . .
C17 C 0.9630(3) 0.22460(15) 1.1675(5) 0.0320(10) Uani 1 1 d . . . . .
H17 H 0.960551 0.200699 1.120182 0.038 Uiso 1 1 calc R . . . .
C40 C 0.9931(3) 0.01007(15) 1.1812(4) 0.0320(10) Uani 1 1 d . . . . .
H40 H 0.997336 0.036133 1.147007 0.038 Uiso 1 1 calc R . . . .
C11 C 0.5878(3) 0.11223(13) 1.4588(4) 0.0247(9) Uani 1 1 d . . . . .
C22 C 0.7709(3) 0.20328(13) 1.3766(4) 0.0264(9) Uani 1 1 d . . . . .
C8 C 0.7056(4) 0.10861(16) 1.6724(5) 0.0355(11) Uani 1 1 d . . . . .
H8 H 0.745207 0.106703 1.744834 0.043 Uiso 1 1 calc R . . . .
C25 C 0.6352(4) 0.21773(15) 1.5313(5) 0.0365(12) Uani 1 1 d . . . . .
C7 C 0.6127(4) 0.10976(17) 1.6814(5) 0.0387(12) Uani 1 1 d . . . . .
H7 H 0.590702 0.109344 1.759265 0.046 Uiso 1 1 calc R . . . .
C48 C 0.3452(3) 0.10133(16) 0.8973(5) 0.0349(11) Uani 1 1 d . . . . .
C39 C 0.9293(3) 0.00285(13) 1.2683(4) 0.0231(9) Uani 1 1 d . . . . .
C28 C 0.9861(3) 0.15569(13) 1.3786(4) 0.0252(9) Uani 1 1 d . . . . .
H28 H 1.013884 0.181022 1.395556 0.030 Uiso 1 1 calc R . . . .
C33 C 0.7957(3) 0.02277(12) 1.3893(4) 0.0230(9) Uani 1 1 d . . . . .
C6 C 0.5498(3) 0.11160(15) 1.5724(4) 0.0304(10) Uani 1 1 d . . . . .
C9 C 0.7433(3) 0.11021(14) 1.5564(4) 0.0272(9) Uani 1 1 d . . . . .
H9 H 0.806480 0.110246 1.552630 0.033 Uiso 1 1 calc R . . . .
C46 C 0.4602(3) 0.07081(14) 1.0495(4) 0.0260(9) Uani 1 1 d . . . . .
C42 C 1.0407(3) -0.05970(15) 1.1965(5) 0.0337(11) Uani 1 1 d . . . . .
C3 C 0.4400(3) 0.11468(17) 1.3385(5) 0.0368(12) Uani 1 1 d . . . . .
H3 H 0.403384 0.115348 1.263239 0.044 Uiso 1 1 calc R . . . .
C23 C 0.6813(3) 0.21070(14) 1.3283(5) 0.0312(10) Uani 1 1 d . . . . .
H23 H 0.667084 0.210658 1.242558 0.037 Uiso 1 1 calc R . . . .
C16 C 0.9069(3) 0.22829(13) 1.2634(4) 0.0246(9) Uani 1 1 d . . . . .
C35 C 0.6440(4) -0.00025(17) 1.4281(5) 0.0389(12) Uani 1 1 d . . . . .
H35 H 0.584124 -0.007310 1.399471 0.047 Uiso 1 1 calc R . . . .
C41 C 1.0495(3) -0.02114(15) 1.1459(5) 0.0342(11) Uani 1 1 d . . . . .
H41 H 1.092241 -0.016196 1.089467 0.041 Uiso 1 1 calc R . . . .
C38 C 0.8230(3) 0.02023(14) 1.5155(4) 0.0282(10) Uani 1 1 d . . . . .
H38 H 0.883035 0.026760 1.544996 0.034 Uiso 1 1 calc R . . . .
C34 C 0.7063(3) 0.01214(14) 1.3466(5) 0.0277(9) Uani 1 1 d . . . . .
H34 H 0.687808 0.013340 1.261917 0.033 Uiso 1 1 calc R . . . .
C36 C 0.6740(4) -0.00169(16) 1.5521(5) 0.0387(12) Uani 1 1 d . . . . .
C27 C 0.7908(3) 0.20414(14) 1.5055(5) 0.0299(10) Uani 1 1 d . . . . .
H27 H 0.850698 0.199456 1.539488 0.036 Uiso 1 1 calc R . . . .
C50 C 0.4720(3) 0.14334(15) 0.9890(5) 0.0332(11) Uani 1 1 d . . . . .
C5 C 0.4527(4) 0.11335(18) 1.5655(5) 0.0410(13) Uani 1 1 d . . . . .
H5 H 0.423899 0.113322 1.638387 0.049 Uiso 1 1 calc R . . . .
C37 C 0.7619(4) 0.00810(15) 1.5978(5) 0.0362(11) Uani 1 1 d . . . . .
H37 H 0.780013 0.006595 1.682599 0.043 Uiso 1 1 calc R . . . .
C43 C 0.9806(3) -0.06794(14) 1.2813(5) 0.0287(10) Uani 1 1 d . . . . .
H43 H 0.976862 -0.094164 1.314575 0.034 Uiso 1 1 calc R . . . .
C24 C 0.6122(3) 0.21819(15) 1.4044(5) 0.0372(12) Uani 1 1 d . . . . .
H24 H 0.552395 0.223357 1.371013 0.045 Uiso 1 1 calc R . . . .
C18 C 1.0230(4) 0.25587(15) 1.1408(5) 0.0360(11) Uani 1 1 d . . . . .
H18 H 1.061574 0.253025 1.077914 0.043 Uiso 1 1 calc R . . . .
C49 C 0.3920(4) 0.13871(17) 0.9112(5) 0.0399(12) Uani 1 1 d . . . . .
H49 H 0.368320 0.161356 0.866404 0.048 Uiso 1 1 calc R . . . .
C4 C 0.4009(4) 0.11509(19) 1.4537(6) 0.0454(14) Uani 1 1 d . . . . .
H4 H 0.337451 0.116594 1.452851 0.054 Uiso 1 1 calc R . . . .
C19 C 1.0229(4) 0.29139(16) 1.2116(5) 0.0396(12) Uani 1 1 d . . . . .
C20 C 0.9678(4) 0.29669(15) 1.3044(5) 0.0378(12) Uani 1 1 d . . . . .
H20 H 0.968744 0.321154 1.348998 0.045 Uiso 1 1 calc R . . . .
C52 C 0.4943(3) 0.03414(14) 1.1244(5) 0.0304(10) Uani 1 1 d . . . . .
H52A H 0.555277 0.027487 1.105586 0.046 Uiso 1 1 calc GR . . . .
H52B H 0.454510 0.011169 1.104108 0.046 Uiso 1 1 calc GR . . . .
H52C H 0.494966 0.040284 1.211301 0.046 Uiso 1 1 calc GR . . . .
C51 C 0.5180(4) 0.18442(17) 1.0039(6) 0.0525(16) Uani 1 1 d . . . . .
H51A H 0.516209 0.193846 1.087777 0.079 Uiso 1 1 calc GR . . . .
H51B H 0.486567 0.203738 0.947664 0.079 Uiso 1 1 calc GR . . . .
H51C H 0.580603 0.182002 0.985785 0.079 Uiso 1 1 calc GR . . . .
C53 C 0.2589(4) 0.0974(2) 0.8093(7) 0.0574(17) Uani 1 1 d . . . . .
H53A H 0.272748 0.083515 0.735040 0.086 Uiso 1 1 calc GR . . . .
H53B H 0.235148 0.124284 0.788309 0.086 Uiso 1 1 calc GR . . . .
H53C H 0.213961 0.081963 0.848585 0.086 Uiso 1 1 calc GR . . . .
F4 F 1.0946(2) -0.09085(10) 1.1600(3) 0.0468(8) Uani 1 1 d . . . . .
O2 O 1.1712(2) 0.09284(12) 1.4958(4) 0.0460(10) Uani 1 1 d . . . C 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br2 Ni1 2.3406(8) . ?
Ni1 Br1 2.3205(8) . ?
Ni1 N2 2.051(4) . ?
Ni1 N1 2.014(4) . ?
N2 C12 1.296(5) . ?
N2 C13 1.428(5) . ?
C1 N1 1.279(6) . ?
C1 C12 1.503(6) . ?
C1 C2 1.469(6) . ?
N1 C45 1.449(5) . ?
F1 C25 1.356(6) . ?
F2 C19 1.370(6) . ?
C12 C10 1.459(6) . ?
C45 C46 1.403(6) . ?
C45 C50 1.401(6) . ?
C13 C31 1.415(6) . ?
C13 C14 1.411(6) . ?
C15 C14 1.533(6) . ?
C15 C22 1.513(6) . ?
C15 C16 1.530(6) . ?
N3 C29 1.474(6) . ?
N3 O1 1.222(5) . ?
N3 O2 1.222(5) . ?
C30 C31 1.391(6) . ?
C30 C29 1.390(6) . ?
F3 C36 1.363(6) . ?
C32 C31 1.529(6) . ?
C32 C39 1.518(6) . ?
C32 C33 1.530(6) . ?
C2 C11 1.415(6) . ?
C2 C3 1.377(6) . ?
C29 C28 1.377(6) . ?
C47 C48 1.390(7) . ?
C47 C46 1.399(6) . ?
C44 C39 1.388(6) . ?
C44 C43 1.393(6) . ?
C10 C11 1.422(6) . ?
C10 C9 1.376(6) . ?
C21 C16 1.384(6) . ?
C21 C20 1.405(7) . ?
C26 C25 1.376(8) . ?
C26 C27 1.381(7) . ?
C14 C28 1.398(6) . ?
C17 C16 1.390(7) . ?
C17 C18 1.393(7) . ?
C40 C39 1.409(6) . ?
C40 C41 1.387(6) . ?
C11 C6 1.398(6) . ?
C22 C23 1.386(7) . ?
C22 C27 1.395(7) . ?
C8 C7 1.376(7) . ?
C8 C9 1.419(7) . ?
C25 C24 1.380(8) . ?
C7 C6 1.425(7) . ?
C48 C49 1.397(7) . ?
C48 C53 1.512(7) . ?
C33 C38 1.387(6) . ?
C33 C34 1.390(6) . ?
C6 C5 1.418(7) . ?
C46 C52 1.500(6) . ?
C42 C41 1.380(7) . ?
C42 C43 1.358(7) . ?
C42 F4 1.367(5) . ?
C3 C4 1.420(7) . ?
C23 C24 1.386(7) . ?
C35 C34 1.388(7) . ?
C35 C36 1.371(8) . ?
C38 C37 1.380(7) . ?
C36 C37 1.372(8) . ?
C50 C49 1.383(7) . ?
C50 C51 1.499(7) . ?
C5 C4 1.364(8) . ?
C18 C19 1.386(7) . ?
C19 C20 1.359(8) . ?

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
Br1 Ni1 Br2 124.52(3) . . ?
N2 Ni1 Br2 114.25(10) . . ?
N2 Ni1 Br1 108.24(10) . . ?
N1 Ni1 Br2 104.15(10) . . ?
N1 Ni1 Br1 115.21(10) . . ?
N1 Ni1 N2 82.85(14) . . ?
C12 N2 Ni1 110.4(3) . . ?
C12 N2 C13 121.3(4) . . ?
C13 N2 Ni1 128.4(3) . . ?
N1 C1 C12 117.8(4) . . ?
N1 C1 C2 135.1(4) . . ?
C2 C1 C12 107.1(4) . . ?
C1 N1 Ni1 111.7(3) . . ?
C1 N1 C45 122.2(4) . . ?
C45 N1 Ni1 125.7(3) . . ?
N2 C12 C1 117.1(4) . . ?
N2 C12 C10 135.2(4) . . ?
C10 C12 C1 107.7(4) . . ?
C46 C45 N1 118.3(4) . . ?
C50 C45 N1 119.0(4) . . ?
C50 C45 C46 122.7(4) . . ?
C31 C13 N2 119.2(3) . . ?
C14 C13 N2 118.3(4) . . ?
C14 C13 C31 122.2(4) . . ?
C22 C15 C14 112.5(4) . . ?
C22 C15 C16 115.2(4) . . ?
C16 C15 C14 111.6(4) . . ?
O1 N3 C29 118.0(4) . . ?
O1 N3 O2 123.4(4) . . ?
O2 N3 C29 118.6(4) . . ?
C29 C30 C31 119.3(4) . . ?
C31 C32 C33 112.0(3) . . ?
C39 C32 C31 114.2(4) . . ?
C39 C32 C33 113.0(3) . . ?
C13 C31 C32 119.9(4) . . ?
C30 C31 C13 118.0(4) . . ?
C30 C31 C32 122.1(4) . . ?
C11 C2 C1 105.6(4) . . ?
C3 C2 C1 134.6(4) . . ?
C3 C2 C11 119.8(4) . . ?
C30 C29 N3 119.3(4) . . ?
C28 C29 N3 117.6(4) . . ?
C28 C29 C30 123.1(4) . . ?
C48 C47 C46 122.7(4) . . ?
C39 C44 C43 121.2(4) . . ?
C11 C10 C12 105.5(4) . . ?
C9 C10 C12 135.0(4) . . ?
C9 C10 C11 119.5(4) . . ?
C16 C21 C20 120.7(5) . . ?
C25 C26 C27 118.2(5) . . ?
C13 C14 C15 121.8(4) . . ?
C28 C14 C13 117.9(4) . . ?
C28 C14 C15 120.3(4) . . ?
C16 C17 C18 121.5(5) . . ?
C41 C40 C39 120.9(5) . . ?
C2 C11 C10 114.0(4) . . ?
C6 C11 C2 123.0(4) . . ?
C6 C11 C10 122.9(4) . . ?
C23 C22 C15 119.3(4) . . ?
C23 C22 C27 118.1(4) . . ?
C27 C22 C15 122.7(4) . . ?
C7 C8 C9 122.4(5) . . ?
F1 C25 C26 119.0(5) . . ?
F1 C25 C24 118.4(5) . . ?
C26 C25 C24 122.6(5) . . ?
C8 C7 C6 120.5(5) . . ?
C47 C48 C49 117.8(4) . . ?
C47 C48 C53 121.4(5) . . ?
C49 C48 C53 120.8(5) . . ?
C44 C39 C32 121.8(4) . . ?
C44 C39 C40 118.0(4) . . ?
C40 C39 C32 119.9(4) . . ?
C29 C28 C14 119.4(4) . . ?
C38 C33 C32 121.8(4) . . ?
C38 C33 C34 118.9(4) . . ?
C34 C33 C32 119.3(4) . . ?
C11 C6 C7 116.5(4) . . ?
C11 C6 C5 115.9(5) . . ?
C5 C6 C7 127.6(4) . . ?
C10 C9 C8 118.2(4) . . ?
C45 C46 C52 122.9(4) . . ?
C47 C46 C45 116.7(4) . . ?
C47 C46 C52 120.4(4) . . ?
C43 C42 C41 122.6(4) . . ?
C43 C42 F4 118.7(4) . . ?
F4 C42 C41 118.7(5) . . ?
C2 C3 C4 117.4(5) . . ?
C22 C23 C24 121.8(5) . . ?
C21 C16 C15 121.6(4) . . ?
C21 C16 C17 118.8(4) . . ?
C17 C16 C15 119.5(4) . . ?
C36 C35 C34 117.6(5) . . ?
C42 C41 C40 118.4(5) . . ?
C37 C38 C33 120.6(5) . . ?
C35 C34 C33 121.3(5) . . ?
F3 C36 C35 117.8(5) . . ?
F3 C36 C37 119.2(5) . . ?
C35 C36 C37 123.0(5) . . ?
C26 C27 C22 121.5(5) . . ?
C45 C50 C51 121.9(4) . . ?
C49 C50 C45 117.5(4) . . ?
C49 C50 C51 120.6(5) . . ?
C4 C5 C6 121.1(5) . . ?
C36 C37 C38 118.7(5) . . ?
C42 C43 C44 118.8(4) . . ?
C25 C24 C23 117.8(5) . . ?
C19 C18 C17 117.4(5) . . ?
C50 C49 C48 122.6(5) . . ?
C5 C4 C3 122.6(5) . . ?
F2 C19 C18 117.8(5) . . ?
C20 C19 F2 119.1(5) . . ?
C20 C19 C18 123.1(5) . . ?
C19 C20 C21 118.4(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
#==END
