# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 1983239'
loop_
_audit_author_name
_audit_author_address
'David Herbert'
;University of Manitoba
Canada
;
_audit_update_record             
;
2020-02-10 deposited with the CCDC.	2020-04-12 downloaded from the CCDC.
;
_audit_creation_date             2019-07-27
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H17 Cl2 F2 N3 Zn, C2 H3 N'
_chemical_formula_sum            'C23 H20 Cl2 F2 N4 Zn'
_chemical_formula_weight         526.70
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.8832(3)
_cell_length_b                   12.6990(5)
_cell_length_c                   21.7752(8)
_cell_angle_alpha                105.6760(10)
_cell_angle_beta                 95.8720(10)
_cell_angle_gamma                94.3010(10)
_cell_volume                     2339.09(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9964
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.523
_cell_measurement_theta_min      2.912
_shelx_estimated_absorpt_T_max   0.914
_shelx_estimated_absorpt_T_min   0.718
_exptl_absorpt_coefficient_mu    1.312
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6161
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0967 before and 0.0783 after correction.
The Ratio of minimum to maximum transmission is 0.8263.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0757
_diffrn_reflns_av_unetI/netI     0.0667
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            56870
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.566
_diffrn_reflns_theta_min         2.318
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Quest ECO CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8095
_reflns_number_total             10800
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.631
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     583
_refine_ls_number_reflns         10800
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0618
_refine_ls_restrained_S_all      1.111
_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)+6.5846P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.1038
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C14(H14), C15(H15), C17(H17),
 C18(H18), C20(H20), C21(H21), C25(H25), C26(H26), C27(H27), C32(H32), C33(H33),
  C35(H35), C36(H36), C38(H38), C39(H39), C41(H41), C42(H42)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C9(H9A,H9B,H9C), C23(H23A,H23B,H23C), C30(H30A,H30B,H30C),
 C43(H43A,H43B,H43C), C45(H45A,H45B,H45C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0542(4) 0.5722(3) 0.65647(17) 0.0200(8) Uani 1 1 d . . . . .
C2 C 0.9701(5) 0.6052(3) 0.60324(19) 0.0280(9) Uani 1 1 d . . . . .
H2A H 0.926902 0.674149 0.620808 0.042 Uiso 1 1 calc GR . . . .
H2B H 0.887894 0.547486 0.580951 0.042 Uiso 1 1 calc GR . . . .
H2C H 1.040034 0.615567 0.572849 0.042 Uiso 1 1 calc GR . . . .
C3 C 1.1772(4) 0.6529(3) 0.70056(17) 0.0196(8) Uani 1 1 d . . . . .
C4 C 1.2122(4) 0.7599(3) 0.69731(18) 0.0219(8) Uani 1 1 d . . . . .
H4 H 1.155187 0.787562 0.666875 0.026 Uiso 1 1 calc R . . . .
C5 C 1.3313(4) 0.8246(3) 0.73929(18) 0.0226(8) Uani 1 1 d . . . . .
H5 H 1.357377 0.897821 0.737951 0.027 Uiso 1 1 calc R . . . .
C6 C 1.4131(4) 0.7833(3) 0.78333(18) 0.0221(8) Uani 1 1 d . . . . .
H6 H 1.496048 0.827165 0.812180 0.026 Uiso 1 1 calc R . . . .
C7 C 1.3714(4) 0.6764(3) 0.78454(17) 0.0202(8) Uani 1 1 d . . . . .
C8 C 1.4511(4) 0.6213(3) 0.82928(17) 0.0193(8) Uani 1 1 d . . . . .
C9 C 1.5804(4) 0.6861(3) 0.87678(19) 0.0270(9) Uani 1 1 d . . . . .
H9A H 1.665157 0.701987 0.854039 0.041 Uiso 1 1 calc GR . . . .
H9B H 1.613558 0.643517 0.906173 0.041 Uiso 1 1 calc GR . . . .
H9C H 1.547555 0.755270 0.901375 0.041 Uiso 1 1 calc GR . . . .
C10 C 0.9197(4) 0.3955(3) 0.63276(18) 0.0211(8) Uani 1 1 d . . . . .
C11 C 0.9433(4) 0.3289(3) 0.57381(19) 0.0300(9) Uani 1 1 d . . . . .
H11 H 1.033912 0.341815 0.556024 0.036 Uiso 1 1 calc R . . . .
C12 C 0.8340(5) 0.2429(4) 0.5405(2) 0.0358(10) Uani 1 1 d . . . . .
H12 H 0.847964 0.196340 0.499766 0.043 Uiso 1 1 calc R . . . .
C13 C 0.7062(4) 0.2271(3) 0.5679(2) 0.0302(9) Uani 1 1 d . . . . .
C14 C 0.6798(4) 0.2919(3) 0.6258(2) 0.0301(9) Uani 1 1 d . . . . .
H14 H 0.588098 0.278991 0.642870 0.036 Uiso 1 1 calc R . . . .
C15 C 0.7888(4) 0.3767(3) 0.65940(19) 0.0258(9) Uani 1 1 d . . . . .
H15 H 0.774096 0.421880 0.700435 0.031 Uiso 1 1 calc R . . . .
C16 C 1.4647(4) 0.4604(3) 0.86276(18) 0.0217(8) Uani 1 1 d . . . . .
C17 C 1.3804(4) 0.4330(3) 0.90707(18) 0.0257(9) Uani 1 1 d . . . . .
H17 H 1.280549 0.454204 0.910134 0.031 Uiso 1 1 calc R . . . .
C18 C 1.4412(5) 0.3746(3) 0.94700(19) 0.0315(10) Uani 1 1 d . . . . .
H18 H 1.385046 0.357017 0.978406 0.038 Uiso 1 1 calc R . . . .
C19 C 1.5836(5) 0.3427(3) 0.9405(2) 0.0335(10) Uani 1 1 d . . . . .
C20 C 1.6695(5) 0.3658(3) 0.8957(2) 0.0345(10) Uani 1 1 d . . . . .
H20 H 1.767516 0.341532 0.891834 0.041 Uiso 1 1 calc R . . . .
C21 C 1.6085(4) 0.4258(3) 0.8564(2) 0.0307(9) Uani 1 1 d . . . . .
H21 H 1.665144 0.443176 0.825034 0.037 Uiso 1 1 calc R . . . .
Cl1 Cl 1.31321(11) 0.32452(8) 0.68091(5) 0.0293(2) Uani 1 1 d . . . . .
Cl2 Cl 1.02977(11) 0.39292(8) 0.80282(4) 0.0260(2) Uani 1 1 d . . . . .
F1 F 0.5998(3) 0.1413(2) 0.53571(13) 0.0470(7) Uani 1 1 d . . . . .
F2 F 1.6427(3) 0.2851(2) 0.97975(13) 0.0500(7) Uani 1 1 d . . . . .
N1 N 1.0343(3) 0.4809(2) 0.66979(14) 0.0207(7) Uani 1 1 d . . . . .
N2 N 1.2550(3) 0.6139(2) 0.74380(14) 0.0173(6) Uani 1 1 d . . . . .
N3 N 1.3984(3) 0.5217(2) 0.82274(15) 0.0211(7) Uani 1 1 d . . . . .
Zn1 Zn 1.19664(5) 0.45365(3) 0.74652(2) 0.01885(10) Uani 1 1 d . . . . .
C22 C 0.0476(4) -0.0567(3) 0.27079(17) 0.0191(8) Uani 1 1 d . . . . .
C23 C 0.0449(5) -0.1190(3) 0.31975(19) 0.0270(9) Uani 1 1 d . . . . .
H23A H -0.047117 -0.106967 0.340873 0.041 Uiso 1 1 calc GR . . . .
H23B H 0.135007 -0.093239 0.351904 0.041 Uiso 1 1 calc GR . . . .
H23C H 0.044936 -0.197602 0.298678 0.041 Uiso 1 1 calc GR . . . .
C24 C -0.0928(4) -0.0682(3) 0.22474(17) 0.0178(7) Uani 1 1 d . . . . .
C25 C -0.2205(4) -0.1404(3) 0.22187(18) 0.0227(8) Uani 1 1 d . . . . .
H25 H -0.222463 -0.185740 0.250155 0.027 Uiso 1 1 calc R . . . .
C26 C -0.3443(4) -0.1451(3) 0.17714(19) 0.0246(8) Uani 1 1 d . . . . .
H26 H -0.432990 -0.193425 0.174693 0.029 Uiso 1 1 calc R . . . .
C27 C -0.3395(4) -0.0798(3) 0.13605(18) 0.0218(8) Uani 1 1 d . . . . .
H27 H -0.424161 -0.082478 0.105028 0.026 Uiso 1 1 calc R . . . .
C28 C -0.2079(4) -0.0096(3) 0.14093(17) 0.0170(7) Uani 1 1 d . . . . .
C29 C -0.1888(4) 0.0655(3) 0.09948(17) 0.0179(7) Uani 1 1 d . . . . .
C30 C -0.3174(4) 0.0678(3) 0.05043(19) 0.0278(9) Uani 1 1 d . . . . .
H30A H -0.321916 0.003191 0.013239 0.042 Uiso 1 1 calc GR . . . .
H30B H -0.301870 0.134794 0.036698 0.042 Uiso 1 1 calc GR . . . .
H30C H -0.413188 0.066971 0.069104 0.042 Uiso 1 1 calc GR . . . .
C31 C 0.3025(4) 0.0176(3) 0.30168(17) 0.0197(8) Uani 1 1 d . . . . .
C32 C 0.3845(4) -0.0726(3) 0.29522(18) 0.0242(8) Uani 1 1 d . . . . .
H32 H 0.344097 -0.141284 0.265904 0.029 Uiso 1 1 calc R . . . .
C33 C 0.5249(4) -0.0631(3) 0.33128(19) 0.0262(9) Uani 1 1 d . . . . .
H33 H 0.582169 -0.124345 0.326932 0.031 Uiso 1 1 calc R . . . .
C34 C 0.5793(4) 0.0366(3) 0.37330(19) 0.0265(9) Uani 1 1 d . . . . .
C35 C 0.5007(5) 0.1284(3) 0.38098(19) 0.0275(9) Uani 1 1 d . . . . .
H35 H 0.541079 0.196585 0.410864 0.033 Uiso 1 1 calc R . . . .
C36 C 0.3616(4) 0.1179(3) 0.34384(17) 0.0222(8) Uani 1 1 d . . . . .
H36 H 0.306337 0.180020 0.347317 0.027 Uiso 1 1 calc R . . . .
C37 C -0.0258(4) 0.1979(3) 0.07324(17) 0.0190(8) Uani 1 1 d . . . . .
C38 C -0.0027(4) 0.3093(3) 0.10312(18) 0.0227(8) Uani 1 1 d . . . . .
H38 H -0.011251 0.336117 0.147644 0.027 Uiso 1 1 calc R . . . .
C39 C 0.0332(4) 0.3823(3) 0.06814(18) 0.0244(8) Uani 1 1 d . . . . .
H39 H 0.047718 0.459432 0.087899 0.029 Uiso 1 1 calc R . . . .
C40 C 0.0471(4) 0.3400(3) 0.00444(19) 0.0259(9) Uani 1 1 d . . . . .
C41 C 0.0259(5) 0.2298(3) -0.0263(2) 0.0316(10) Uani 1 1 d . . . . .
H41 H 0.037200 0.203365 -0.070596 0.038 Uiso 1 1 calc R . . . .
C42 C -0.0123(5) 0.1578(3) 0.00868(19) 0.0268(9) Uani 1 1 d . . . . .
H42 H -0.029291 0.080911 -0.011675 0.032 Uiso 1 1 calc R . . . .
Cl3 Cl 0.17470(11) 0.26842(7) 0.24763(4) 0.0244(2) Uani 1 1 d . . . . .
Cl4 Cl 0.27946(10) 0.01716(8) 0.12245(5) 0.0256(2) Uani 1 1 d . . . . .
F3 F 0.7186(3) 0.0468(2) 0.40790(13) 0.0436(7) Uani 1 1 d . . . . .
F4 F 0.0840(3) 0.4109(2) -0.02994(12) 0.0407(6) Uani 1 1 d . . . . .
N4 N 0.1587(3) 0.0079(2) 0.26369(14) 0.0188(6) Uani 1 1 d . . . . .
N5 N -0.0880(3) -0.0053(2) 0.18440(14) 0.0162(6) Uani 1 1 d . . . . .
N6 N -0.0596(3) 0.1244(2) 0.11067(14) 0.0187(6) Uani 1 1 d . . . . .
Zn2 Zn 0.11197(5) 0.09392(3) 0.18753(2) 0.01743(10) Uani 1 1 d . . . . .
C43 C 1.5177(6) 0.5488(5) 0.6214(3) 0.0569(14) Uani 1 1 d . . . . .
H43A H 1.609689 0.525756 0.602561 0.085 Uiso 1 1 calc GR . . . .
H43B H 1.490677 0.502887 0.649098 0.085 Uiso 1 1 calc GR . . . .
H43C H 1.536793 0.625993 0.646963 0.085 Uiso 1 1 calc GR . . . .
C44 C 1.3995(7) 0.5372(6) 0.5729(3) 0.075(2) Uani 1 1 d . . . . .
N7 N 1.3032(9) 0.5290(11) 0.5339(4) 0.198(6) Uani 1 1 d . . . . .
C45 C 1.2308(8) 0.1237(7) 0.5096(3) 0.094(3) Uani 1 1 d . . . . .
H45A H 1.305877 0.073944 0.493296 0.141 Uiso 1 1 calc GR . . . .
H45B H 1.174296 0.094553 0.538840 0.141 Uiso 1 1 calc GR . . . .
H45C H 1.283097 0.196519 0.532697 0.141 Uiso 1 1 calc GR . . . .
C46 C 1.1262(6) 0.1327(4) 0.4563(2) 0.0407(11) Uani 1 1 d . . . . .
N8 N 1.0454(5) 0.1392(3) 0.4145(2) 0.0458(10) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.486(5) . ?
C1 C3 1.501(5) . ?
C1 N1 1.273(5) . ?
C3 C4 1.393(5) . ?
C3 N2 1.334(4) . ?
C4 C5 1.377(5) . ?
C5 C6 1.381(5) . ?
C6 C7 1.389(5) . ?
C7 C8 1.497(5) . ?
C7 N2 1.339(5) . ?
C8 C9 1.490(5) . ?
C8 N3 1.281(5) . ?
C10 C11 1.379(5) . ?
C10 C15 1.385(5) . ?
C10 N1 1.434(5) . ?
C11 C12 1.390(5) . ?
C12 C13 1.362(6) . ?
C13 C14 1.360(6) . ?
C13 F1 1.368(4) . ?
C14 C15 1.380(5) . ?
C16 C17 1.379(5) . ?
C16 C21 1.390(5) . ?
C16 N3 1.429(5) . ?
C17 C18 1.382(5) . ?
C18 C19 1.366(6) . ?
C19 C20 1.376(6) . ?
C19 F2 1.359(4) . ?
C20 C21 1.388(6) . ?
Cl1 Zn1 2.2570(10) . ?
Cl2 Zn1 2.2375(10) . ?
N1 Zn1 2.210(3) . ?
N2 Zn1 2.080(3) . ?
N3 Zn1 2.258(3) . ?
C22 C23 1.490(5) . ?
C22 C24 1.491(5) . ?
C22 N4 1.284(4) . ?
C24 C25 1.389(5) . ?
C24 N5 1.339(4) . ?
C25 C26 1.379(5) . ?
C26 C27 1.376(5) . ?
C27 C28 1.393(5) . ?
C28 C29 1.492(5) . ?
C28 N5 1.338(4) . ?
C29 C30 1.490(5) . ?
C29 N6 1.285(4) . ?
C31 C32 1.387(5) . ?
C31 C36 1.382(5) . ?
C31 N4 1.427(5) . ?
C32 C33 1.383(5) . ?
C33 C34 1.365(6) . ?
C34 C35 1.384(6) . ?
C34 F3 1.359(4) . ?
C35 C36 1.382(5) . ?
C37 C38 1.378(5) . ?
C37 C42 1.381(5) . ?
C37 N6 1.430(4) . ?
C38 C39 1.389(5) . ?
C39 C40 1.367(5) . ?
C40 C41 1.368(6) . ?
C40 F4 1.359(4) . ?
C41 C42 1.384(5) . ?
Cl3 Zn2 2.2433(10) . ?
Cl4 Zn2 2.2526(10) . ?
N4 Zn2 2.241(3) . ?
N5 Zn2 2.083(3) . ?
N6 Zn2 2.278(3) . ?
C43 C44 1.382(8) . ?
C44 N7 1.119(8) . ?
C45 C46 1.446(8) . ?
C46 N8 1.124(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
C2 C1 C3 118.5(3) . . ?
N1 C1 C2 127.2(3) . . ?
N1 C1 C3 114.4(3) . . ?
C4 C3 C1 124.1(3) . . ?
N2 C3 C1 114.6(3) . . ?
N2 C3 C4 121.2(3) . . ?
C5 C4 C3 118.4(3) . . ?
C4 C5 C6 120.2(3) . . ?
C5 C6 C7 118.6(3) . . ?
C6 C7 C8 124.0(3) . . ?
N2 C7 C6 121.0(3) . . ?
N2 C7 C8 114.9(3) . . ?
C9 C8 C7 118.2(3) . . ?
N3 C8 C7 115.3(3) . . ?
N3 C8 C9 126.5(3) . . ?
C11 C10 C15 120.6(4) . . ?
C11 C10 N1 120.9(3) . . ?
C15 C10 N1 118.4(3) . . ?
C10 C11 C12 119.7(4) . . ?
C13 C12 C11 118.2(4) . . ?
C12 C13 F1 118.2(4) . . ?
C14 C13 C12 123.3(4) . . ?
C14 C13 F1 118.5(4) . . ?
C13 C14 C15 118.7(4) . . ?
C14 C15 C10 119.5(4) . . ?
C17 C16 C21 120.2(4) . . ?
C17 C16 N3 118.3(3) . . ?
C21 C16 N3 121.4(3) . . ?
C16 C17 C18 120.0(4) . . ?
C19 C18 C17 118.8(4) . . ?
C18 C19 C20 122.9(4) . . ?
F2 C19 C18 118.6(4) . . ?
F2 C19 C20 118.5(4) . . ?
C19 C20 C21 118.0(4) . . ?
C20 C21 C16 120.1(4) . . ?
C1 N1 C10 121.3(3) . . ?
C1 N1 Zn1 117.3(2) . . ?
C10 N1 Zn1 121.2(2) . . ?
C3 N2 C7 120.6(3) . . ?
C3 N2 Zn1 119.4(2) . . ?
C7 N2 Zn1 120.0(2) . . ?
C8 N3 C16 120.6(3) . . ?
C8 N3 Zn1 115.9(2) . . ?
C16 N3 Zn1 123.5(2) . . ?
Cl1 Zn1 N3 97.03(9) . . ?
Cl2 Zn1 Cl1 116.40(4) . . ?
Cl2 Zn1 N3 101.44(8) . . ?
N1 Zn1 Cl1 95.97(8) . . ?
N1 Zn1 Cl2 98.82(8) . . ?
N1 Zn1 N3 147.86(11) . . ?
N2 Zn1 Cl1 114.79(8) . . ?
N2 Zn1 Cl2 128.78(8) . . ?
N2 Zn1 N1 74.00(11) . . ?
N2 Zn1 N3 73.87(11) . . ?
C23 C22 C24 117.8(3) . . ?
N4 C22 C23 127.1(3) . . ?
N4 C22 C24 115.1(3) . . ?
C25 C24 C22 123.3(3) . . ?
N5 C24 C22 115.5(3) . . ?
N5 C24 C25 121.1(3) . . ?
C26 C25 C24 118.6(3) . . ?
C27 C26 C25 120.1(3) . . ?
C26 C27 C28 118.5(3) . . ?
C27 C28 C29 123.7(3) . . ?
N5 C28 C27 121.2(3) . . ?
N5 C28 C29 115.1(3) . . ?
C30 C29 C28 118.9(3) . . ?
N6 C29 C28 115.2(3) . . ?
N6 C29 C30 125.8(3) . . ?
C32 C31 N4 120.1(3) . . ?
C36 C31 C32 120.0(3) . . ?
C36 C31 N4 119.8(3) . . ?
C33 C32 C31 120.3(4) . . ?
C34 C33 C32 118.4(4) . . ?
C33 C34 C35 122.9(4) . . ?
F3 C34 C33 118.5(4) . . ?
F3 C34 C35 118.5(4) . . ?
C36 C35 C34 118.0(4) . . ?
C31 C36 C35 120.4(4) . . ?
C38 C37 C42 120.6(3) . . ?
C38 C37 N6 118.8(3) . . ?
C42 C37 N6 120.6(3) . . ?
C37 C38 C39 120.0(3) . . ?
C40 C39 C38 118.1(4) . . ?
C39 C40 C41 123.1(4) . . ?
F4 C40 C39 118.4(4) . . ?
F4 C40 C41 118.4(4) . . ?
C40 C41 C42 118.4(4) . . ?
C37 C42 C41 119.9(4) . . ?
C22 N4 C31 119.6(3) . . ?
C22 N4 Zn2 116.0(2) . . ?
C31 N4 Zn2 124.4(2) . . ?
C24 N5 Zn2 119.1(2) . . ?
C28 N5 C24 120.3(3) . . ?
C28 N5 Zn2 120.5(2) . . ?
C29 N6 C37 120.7(3) . . ?
C29 N6 Zn2 115.7(2) . . ?
C37 N6 Zn2 123.5(2) . . ?
Cl3 Zn2 Cl4 117.30(4) . . ?
Cl3 Zn2 N6 98.79(8) . . ?
Cl4 Zn2 N6 97.69(8) . . ?
N4 Zn2 Cl3 99.14(8) . . ?
N4 Zn2 Cl4 97.84(8) . . ?
N4 Zn2 N6 147.49(11) . . ?
N5 Zn2 Cl3 126.73(8) . . ?
N5 Zn2 Cl4 115.97(8) . . ?
N5 Zn2 N4 74.24(11) . . ?
N5 Zn2 N6 73.29(11) . . ?
N7 C44 C43 179.1(11) . . ?
N8 C46 C45 179.5(6) . . ?

_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_3d
_database_code_depnum_ccdc_archive 'CCDC 1983243'
loop_
_audit_author_name
_audit_author_address
'David Herbert'
;University of Manitoba
Canada
;
_audit_update_record             
;
2020-02-10 deposited with the CCDC.	2020-04-12 downloaded from the CCDC.
;
_audit_creation_date             2020-01-24
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C46 H34 Fe N10, 2(C2 H3 N), 2(F6 P)'
_chemical_formula_sum            'C50 H40 F12 Fe N12 P2'
_chemical_formula_weight         1154.73
_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'
Fe Fe 0.3463 0.8444 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.5217(6)
_cell_length_b                   32.6571(16)
_cell_length_c                   13.8662(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.732(2)
_cell_angle_gamma                90
_cell_volume                     5156.9(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9580
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.754
_cell_measurement_theta_min      2.481
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.904
_exptl_absorpt_coefficient_mu    0.447
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.6238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1006 before and 0.0838 after correction.
The Ratio of minimum to maximum transmission is 0.8372.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plates
_exptl_crystal_F_000             2352
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1056
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            121300
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.850
_diffrn_reflns_theta_max         24.850
_diffrn_reflns_theta_min         2.389
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Quest ECO CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7025
_reflns_number_total             8890
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         1.289
_refine_diff_density_min         -0.975
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     700
_refine_ls_number_reflns         8890
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0717
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0433P)²+21.8202P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1487
_refine_ls_wR_factor_ref         0.1611
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C14(H14), C15(H15), C18(H18),
 C19(H19), C21(H21), C22(H22), C27(H27), C28(H28), C29(H29), C34(H34), C35(H35),
  C37(H37), C38(H38), C41(H41), C42(H42), C44(H44), C45(H45)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C9(H9A,H9B,H9C), C25(H25A,H25B,H25C), C32(H32A,H32B,H32C),
 C47(H47A,H47B,H47C), C49(H49A,H49B,H49C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2636(4) 0.65598(13) -0.0093(3) 0.0241(9) Uani 1 1 d . . . . .
C2 C 0.2004(4) 0.67809(14) -0.0956(3) 0.0317(10) Uani 1 1 d . . . . .
H2A H 0.251911 0.699120 -0.116504 0.047 Uiso 1 1 calc GR . . . .
H2B H 0.129819 0.691060 -0.078006 0.047 Uiso 1 1 calc GR . . . .
H2C H 0.177891 0.658637 -0.148951 0.047 Uiso 1 1 calc GR . . . .
C3 C 0.3517(4) 0.62472(13) -0.0197(3) 0.0234(9) Uani 1 1 d . . . . .
C4 C 0.3933(4) 0.61280(15) -0.1045(3) 0.0309(10) Uani 1 1 d . . . . .
H4 H 0.367581 0.626189 -0.164805 0.037 Uiso 1 1 calc R . . . .
C5 C 0.4733(4) 0.58092(16) -0.0987(3) 0.0378(12) Uani 1 1 d . . . . .
H5 H 0.502387 0.572019 -0.155733 0.045 Uiso 1 1 calc R . . . .
C6 C 0.5110(4) 0.56197(15) -0.0104(3) 0.0342(11) Uani 1 1 d . . . . .
H6 H 0.565010 0.539848 -0.006566 0.041 Uiso 1 1 calc R . . . .
C7 C 0.4695(4) 0.57545(13) 0.0717(3) 0.0238(9) Uani 1 1 d . . . . .
C8 C 0.5046(4) 0.56255(13) 0.1737(3) 0.0244(9) Uani 1 1 d . . . . .
C9 C 0.5876(4) 0.52815(14) 0.2014(3) 0.0354(11) Uani 1 1 d . . . . .
H9A H 0.579236 0.507796 0.148892 0.053 Uiso 1 1 calc GR . . . .
H9B H 0.570105 0.515378 0.261516 0.053 Uiso 1 1 calc GR . . . .
H9C H 0.668296 0.538619 0.212090 0.053 Uiso 1 1 calc GR . . . .
C10 C 0.1613(4) 0.68973(13) 0.1061(3) 0.0243(9) Uani 1 1 d . . . . .
C11 C 0.1874(4) 0.73086(15) 0.1087(4) 0.0376(12) Uani 1 1 d . . . . .
H11 H 0.258173 0.740292 0.089068 0.045 Uiso 1 1 calc R . . . .
C12 C 0.1100(5) 0.75841(16) 0.1402(4) 0.0440(13) Uani 1 1 d . . . . .
H12 H 0.127957 0.786826 0.142170 0.053 Uiso 1 1 calc R . . . .
C13 C 0.0079(5) 0.74497(16) 0.1683(3) 0.0409(13) Uani 1 1 d . . . . .
C14 C -0.0201(4) 0.70313(17) 0.1636(4) 0.0423(13) Uani 1 1 d . . . . .
H14 H -0.091778 0.693729 0.181644 0.051 Uiso 1 1 calc R . . . .
C15 C 0.0579(4) 0.67572(15) 0.1324(3) 0.0337(11) Uani 1 1 d . . . . .
H15 H 0.040118 0.647297 0.129205 0.040 Uiso 1 1 calc R . . . .
C16 C -0.0725(6) 0.7736(2) 0.2021(4) 0.0606(18) Uani 1 1 d . . . . .
C17 C 0.4886(4) 0.57889(13) 0.3391(3) 0.0236(9) Uani 1 1 d . . . . .
C18 C 0.5827(4) 0.60016(15) 0.3876(3) 0.0320(11) Uani 1 1 d . . . . .
H18 H 0.627721 0.617604 0.352824 0.038 Uiso 1 1 calc R . . . .
C19 C 0.6112(4) 0.59588(16) 0.4877(3) 0.0392(12) Uani 1 1 d . . . . .
H19 H 0.676723 0.610075 0.521998 0.047 Uiso 1 1 calc R . . . .
C20 C 0.5432(4) 0.57064(16) 0.5379(3) 0.0349(11) Uani 1 1 d . . . . .
C21 C 0.4477(4) 0.55039(16) 0.4890(3) 0.0390(12) Uani 1 1 d . . . . .
H21 H 0.400398 0.533818 0.523829 0.047 Uiso 1 1 calc R . . . .
C22 C 0.4206(4) 0.55420(15) 0.3891(3) 0.0331(11) Uani 1 1 d . . . . .
H22 H 0.355340 0.539881 0.354692 0.040 Uiso 1 1 calc R . . . .
C23 C 0.5760(5) 0.56486(19) 0.6408(4) 0.0463(14) Uani 1 1 d . . . . .
C24 C 0.1666(4) 0.59466(14) 0.2739(3) 0.0261(10) Uani 1 1 d . . . . .
C25 C 0.0688(4) 0.57066(16) 0.3041(3) 0.0359(11) Uani 1 1 d . . . . .
H25A H 0.095986 0.557062 0.366489 0.054 Uiso 1 1 calc GR . . . .
H25B H 0.042255 0.550006 0.254370 0.054 Uiso 1 1 calc GR . . . .
H25C H 0.003488 0.589050 0.311537 0.054 Uiso 1 1 calc GR . . . .
C26 C 0.2190(4) 0.62891(13) 0.3351(3) 0.0245(9) Uani 1 1 d . . . . .
C27 C 0.1935(4) 0.64107(15) 0.4256(3) 0.0337(11) Uani 1 1 d . . . . .
H27 H 0.132766 0.628174 0.453682 0.040 Uiso 1 1 calc R . . . .
C28 C 0.2590(5) 0.67239(16) 0.4736(3) 0.0388(12) Uani 1 1 d . . . . .
H28 H 0.243951 0.680915 0.535994 0.047 Uiso 1 1 calc R . . . .
C29 C 0.3462(4) 0.69147(15) 0.4318(3) 0.0355(11) Uani 1 1 d . . . . .
H29 H 0.390319 0.713275 0.464566 0.043 Uiso 1 1 calc R . . . .
C30 C 0.3682(4) 0.67830(13) 0.3412(3) 0.0266(10) Uani 1 1 d . . . . .
C31 C 0.4576(4) 0.69283(13) 0.2842(3) 0.0265(10) Uani 1 1 d . . . . .
C32 C 0.5321(4) 0.72904(14) 0.3173(4) 0.0372(11) Uani 1 1 d . . . . .
H32A H 0.483912 0.753898 0.309610 0.056 Uiso 1 1 calc GR . . . .
H32B H 0.595551 0.731369 0.277888 0.056 Uiso 1 1 calc GR . . . .
H32C H 0.565694 0.725633 0.386087 0.056 Uiso 1 1 calc GR . . . .
C33 C 0.1869(3) 0.55463(13) 0.1318(3) 0.0234(9) Uani 1 1 d . . . . .
C34 C 0.2176(4) 0.51538(14) 0.1633(3) 0.0308(10) Uani 1 1 d . . . . .
H34 H 0.247134 0.510584 0.230081 0.037 Uiso 1 1 calc R . . . .
C35 C 0.2057(4) 0.48310(15) 0.0982(3) 0.0321(11) Uani 1 1 d . . . . .
H35 H 0.226577 0.456153 0.120101 0.039 Uiso 1 1 calc R . . . .
C36 C 0.1629(4) 0.49023(14) 0.0003(3) 0.0277(10) Uani 1 1 d . . . . .
C37 C 0.1287(4) 0.52954(14) -0.0313(3) 0.0294(10) Uani 1 1 d . . . . .
H37 H 0.097484 0.534264 -0.097813 0.035 Uiso 1 1 calc R . . . .
C38 C 0.1404(4) 0.56137(14) 0.0340(3) 0.0273(10) Uani 1 1 d . . . . .
H38 H 0.116802 0.588157 0.012664 0.033 Uiso 1 1 calc R . . . .
C39 C 0.1578(4) 0.45642(16) -0.0675(3) 0.0342(11) Uani 1 1 d . . . . .
C40 C 0.5388(4) 0.68171(13) 0.1372(3) 0.0256(9) Uani 1 1 d . . . . .
C41 C 0.6311(4) 0.65600(13) 0.1248(3) 0.0259(10) Uani 1 1 d . . . . .
H41 H 0.648940 0.633197 0.166951 0.031 Uiso 1 1 calc R . . . .
C42 C 0.6970(4) 0.66327(14) 0.0519(3) 0.0307(10) Uani 1 1 d . . . . .
H42 H 0.759714 0.645417 0.043386 0.037 Uiso 1 1 calc R . . . .
C43 C 0.6716(4) 0.69675(14) -0.0093(3) 0.0315(10) Uani 1 1 d . . . . .
C44 C 0.5807(4) 0.72318(15) 0.0039(4) 0.0366(11) Uani 1 1 d . . . . .
H44 H 0.564000 0.746359 -0.037317 0.044 Uiso 1 1 calc R . . . .
C45 C 0.5147(4) 0.71548(14) 0.0774(4) 0.0341(11) Uani 1 1 d . . . . .
H45 H 0.452561 0.733468 0.086710 0.041 Uiso 1 1 calc R . . . .
C46 C 0.7375(5) 0.70496(15) -0.0875(4) 0.0421(13) Uani 1 1 d . . . . .
Fe1 Fe 0.34476(5) 0.62668(2) 0.17940(4) 0.01978(16) Uani 1 1 d . . . . .
N1 N 0.2460(3) 0.66071(10) 0.0808(2) 0.0215(7) Uani 1 1 d . . . . .
N2 N 0.3914(3) 0.60635(10) 0.0660(2) 0.0203(7) Uani 1 1 d . . . . .
N3 N 0.4572(3) 0.58470(10) 0.2354(2) 0.0211(7) Uani 1 1 d . . . . .
N4 N 0.6070(4) 0.5595(2) 0.7223(3) 0.0687(17) Uani 1 1 d . . . . .
N5 N -0.1350(6) 0.7972(2) 0.2270(4) 0.092(2) Uani 1 1 d . . . . .
N6 N 0.2146(3) 0.58915(11) 0.1960(2) 0.0236(8) Uani 1 1 d . . . . .
N7 N 0.3051(3) 0.64732(11) 0.2955(2) 0.0217(8) Uani 1 1 d . . . . .
N8 N 0.4615(3) 0.67137(11) 0.2059(2) 0.0238(8) Uani 1 1 d . . . . .
N9 N 0.1572(4) 0.42955(14) -0.1202(3) 0.0485(12) Uani 1 1 d . . . . .
N10 N 0.7886(5) 0.71230(15) -0.1496(4) 0.0565(13) Uani 1 1 d . . . . .
C47 C 1.1272(6) 0.3726(2) 0.2765(4) 0.072(2) Uani 1 1 d . . . . .
H47A H 1.202485 0.358151 0.290107 0.108 Uiso 1 1 calc GR . . . .
H47B H 1.066584 0.356707 0.302131 0.108 Uiso 1 1 calc GR . . . .
H47C H 1.134569 0.399577 0.307810 0.108 Uiso 1 1 calc GR . . . .
C48 C 1.0950(5) 0.37761(17) 0.1724(5) 0.0484(14) Uani 1 1 d . . . . .
N11 N 1.0708(5) 0.38129(17) 0.0910(4) 0.0677(15) Uani 1 1 d . . . . .
C49 C 0.8867(5) 0.54204(17) 0.4593(4) 0.0498(14) Uani 1 1 d . . . . .
H49A H 0.829686 0.558164 0.415308 0.075 Uiso 1 1 calc GR . . . .
H49B H 0.915917 0.519494 0.423013 0.075 Uiso 1 1 calc GR . . . .
H49C H 0.952536 0.559600 0.486740 0.075 Uiso 1 1 calc GR . . . .
C50 C 0.8302(4) 0.52542(15) 0.5384(4) 0.0359(11) Uani 1 1 d . . . . .
N12 N 0.7876(4) 0.51238(14) 0.5977(3) 0.0467(11) Uani 1 1 d . . . . .
F1 F -0.0347(3) 0.68822(11) 0.3874(3) 0.0650(10) Uani 1 1 d . . . . .
F2 F -0.2265(3) 0.67509(11) 0.3344(2) 0.0635(10) Uani 1 1 d . . . . .
F3 F -0.1728(3) 0.73201(9) 0.4220(2) 0.0531(8) Uani 1 1 d . . . . .
F4 F -0.2658(3) 0.68099(11) 0.4858(3) 0.0683(10) Uani 1 1 d . . . . .
F5 F -0.0740(4) 0.69368(11) 0.5400(2) 0.0750(12) Uani 1 1 d . . . . .
F6 F -0.1280(3) 0.63688(9) 0.4545(3) 0.0721(11) Uani 1 1 d . . . . .
P1 P -0.14948(12) 0.68429(4) 0.43657(10) 0.0380(3) Uani 1 1 d . . . . .
F7 F 0.8151(5) 0.4446(2) 0.4296(4) 0.138(2) Uani 1 1 d . . . . .
F8 F 0.7477(5) 0.4617(2) 0.2672(9) 0.250(6) Uani 1 1 d . . . . .
F9 F 0.9328(4) 0.45641(16) 0.3192(3) 0.1016(16) Uani 1 1 d . . . . .
F10 F 0.8437(4) 0.40834(14) 0.2298(3) 0.0966(15) Uani 1 1 d . . . . .
F11 F 0.8972(6) 0.3942(2) 0.3784(5) 0.174(3) Uani 1 1 d . . . . .
F12 F 0.7050(4) 0.40492(17) 0.3283(3) 0.1091(18) Uani 1 1 d . . . . .
P2 P 0.82042(13) 0.43064(5) 0.32407(10) 0.0489(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.489(6) . ?
C1 C3 1.461(6) . ?
C1 N1 1.305(5) . ?
C3 C4 1.391(6) . ?
C3 N2 1.348(5) . ?
C4 C5 1.385(7) . ?
C5 C6 1.382(7) . ?
C6 C7 1.372(6) . ?
C7 C8 1.473(6) . ?
C7 N2 1.347(5) . ?
C8 C9 1.488(6) . ?
C8 N3 1.302(5) . ?
C10 C11 1.376(6) . ?
C10 C15 1.377(6) . ?
C10 N1 1.441(5) . ?
C11 C12 1.382(7) . ?
C12 C13 1.368(7) . ?
C13 C14 1.403(8) . ?
C13 C16 1.442(7) . ?
C14 C15 1.383(7) . ?
C16 N5 1.144(7) . ?
C17 C18 1.375(6) . ?
C17 C22 1.382(6) . ?
C17 N3 1.441(5) . ?
C18 C19 1.383(6) . ?
C19 C20 1.394(7) . ?
C20 C21 1.372(7) . ?
C20 C23 1.432(6) . ?
C21 C22 1.379(6) . ?
C23 N4 1.146(6) . ?
C24 C25 1.484(6) . ?
C24 C26 1.476(6) . ?
C24 N6 1.299(5) . ?
C26 C27 1.389(6) . ?
C26 N7 1.346(5) . ?
C27 C28 1.380(7) . ?
C28 C29 1.382(7) . ?
C29 C30 1.387(6) . ?
C30 C31 1.468(6) . ?
C30 N7 1.347(5) . ?
C31 C32 1.492(6) . ?
C31 N8 1.299(5) . ?
C33 C34 1.383(6) . ?
C33 C38 1.398(6) . ?
C33 N6 1.442(5) . ?
C34 C35 1.381(6) . ?
C35 C36 1.391(6) . ?
C36 C37 1.394(6) . ?
C36 C39 1.446(7) . ?
C37 C38 1.372(6) . ?
C39 N9 1.141(6) . ?
C40 C41 1.386(6) . ?
C40 C45 1.383(6) . ?
C40 N8 1.440(5) . ?
C41 C42 1.374(6) . ?
C42 C43 1.387(6) . ?
C43 C44 1.391(7) . ?
C43 C46 1.440(7) . ?
C44 C45 1.384(6) . ?
C46 N10 1.140(6) . ?
Fe1 N1 1.981(3) . ?
Fe1 N2 1.860(3) . ?
Fe1 N3 1.963(3) . ?
Fe1 N6 1.977(4) . ?
Fe1 N7 1.865(3) . ?
Fe1 N8 1.980(4) . ?
C47 C48 1.444(8) . ?
C48 N11 1.128(7) . ?
C49 C50 1.462(7) . ?
C50 N12 1.105(6) . ?
F1 P1 1.583(4) . ?
F2 P1 1.582(3) . ?
F3 P1 1.589(3) . ?
F4 P1 1.597(4) . ?
F5 P1 1.590(3) . ?
F6 P1 1.581(3) . ?
F7 P2 1.542(5) . ?
F8 P2 1.466(5) . ?
F9 P2 1.554(4) . ?
F10 P2 1.555(4) . ?
F11 P2 1.600(6) . ?
F12 P2 1.581(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C1 C2 121.5(4) . . ?
N1 C1 C2 125.7(4) . . ?
N1 C1 C3 112.8(4) . . ?
C4 C3 C1 127.8(4) . . ?
N2 C3 C1 111.8(3) . . ?
N2 C3 C4 120.4(4) . . ?
C5 C4 C3 118.2(4) . . ?
C6 C5 C4 120.3(4) . . ?
C7 C6 C5 119.3(4) . . ?
C6 C7 C8 128.7(4) . . ?
N2 C7 C6 120.4(4) . . ?
N2 C7 C8 110.8(3) . . ?
C7 C8 C9 122.4(4) . . ?
N3 C8 C7 113.0(4) . . ?
N3 C8 C9 124.6(4) . . ?
C11 C10 C15 120.8(4) . . ?
C11 C10 N1 119.7(4) . . ?
C15 C10 N1 119.4(4) . . ?
C10 C11 C12 119.7(5) . . ?
C13 C12 C11 120.3(5) . . ?
C12 C13 C14 120.0(5) . . ?
C12 C13 C16 120.5(5) . . ?
C14 C13 C16 119.5(5) . . ?
C15 C14 C13 119.3(5) . . ?
C10 C15 C14 119.8(5) . . ?
N5 C16 C13 177.9(7) . . ?
C18 C17 C22 121.0(4) . . ?
C18 C17 N3 118.8(4) . . ?
C22 C17 N3 120.1(4) . . ?
C17 C18 C19 119.3(4) . . ?
C18 C19 C20 119.7(5) . . ?
C19 C20 C23 119.5(5) . . ?
C21 C20 C19 120.5(4) . . ?
C21 C20 C23 119.9(5) . . ?
C20 C21 C22 119.7(4) . . ?
C21 C22 C17 119.9(4) . . ?
N4 C23 C20 176.8(6) . . ?
C26 C24 C25 120.0(4) . . ?
N6 C24 C25 126.8(4) . . ?
N6 C24 C26 113.2(4) . . ?
C27 C26 C24 127.7(4) . . ?
N7 C26 C24 111.5(3) . . ?
N7 C26 C27 120.7(4) . . ?
C28 C27 C26 118.2(4) . . ?
C27 C28 C29 120.7(4) . . ?
C28 C29 C30 119.0(5) . . ?
C29 C30 C31 128.8(4) . . ?
N7 C30 C29 119.9(4) . . ?
N7 C30 C31 111.3(4) . . ?
C30 C31 C32 120.6(4) . . ?
N8 C31 C30 113.0(4) . . ?
N8 C31 C32 126.4(4) . . ?
C34 C33 C38 119.6(4) . . ?
C34 C33 N6 120.5(4) . . ?
C38 C33 N6 119.5(4) . . ?
C35 C34 C33 120.4(4) . . ?
C34 C35 C36 119.7(4) . . ?
C35 C36 C37 120.2(4) . . ?
C35 C36 C39 118.7(4) . . ?
C37 C36 C39 121.1(4) . . ?
C38 C37 C36 119.7(4) . . ?
C37 C38 C33 120.4(4) . . ?
N9 C39 C36 178.0(5) . . ?
C41 C40 N8 120.3(4) . . ?
C45 C40 C41 119.7(4) . . ?
C45 C40 N8 119.7(4) . . ?
C42 C41 C40 120.5(4) . . ?
C41 C42 C43 119.9(4) . . ?
C42 C43 C44 120.1(4) . . ?
C42 C43 C46 121.4(4) . . ?
C44 C43 C46 118.5(4) . . ?
C45 C44 C43 119.5(4) . . ?
C40 C45 C44 120.3(4) . . ?
N10 C46 C43 178.5(6) . . ?
N2 Fe1 N1 79.97(14) . . ?
N2 Fe1 N3 80.05(14) . . ?
N2 Fe1 N6 101.45(14) . . ?
N2 Fe1 N7 177.45(15) . . ?
N2 Fe1 N8 98.34(14) . . ?
N3 Fe1 N1 159.98(14) . . ?
N3 Fe1 N6 89.29(14) . . ?
N3 Fe1 N8 93.02(14) . . ?
N6 Fe1 N1 93.55(14) . . ?
N6 Fe1 N8 160.18(14) . . ?
N7 Fe1 N1 101.70(14) . . ?
N7 Fe1 N3 98.31(14) . . ?
N7 Fe1 N6 80.44(15) . . ?
N7 Fe1 N8 79.75(15) . . ?
N8 Fe1 N1 90.99(14) . . ?
C1 N1 C10 121.3(3) . . ?
C1 N1 Fe1 116.0(3) . . ?
C10 N1 Fe1 122.7(2) . . ?
C3 N2 Fe1 118.9(3) . . ?
C7 N2 C3 121.3(3) . . ?
C7 N2 Fe1 119.6(3) . . ?
C8 N3 C17 121.0(3) . . ?
C8 N3 Fe1 116.5(3) . . ?
C17 N3 Fe1 122.5(3) . . ?
C24 N6 C33 122.6(4) . . ?
C24 N6 Fe1 115.9(3) . . ?
C33 N6 Fe1 120.9(3) . . ?
C26 N7 C30 121.5(4) . . ?
C26 N7 Fe1 118.9(3) . . ?
C30 N7 Fe1 119.4(3) . . ?
C31 N8 C40 122.0(4) . . ?
C31 N8 Fe1 116.4(3) . . ?
C40 N8 Fe1 121.4(3) . . ?
N11 C48 C47 179.3(7) . . ?
N12 C50 C49 179.1(6) . . ?
F1 P1 F3 90.11(19) . . ?
F1 P1 F4 179.2(2) . . ?
F1 P1 F5 89.7(2) . . ?
F2 P1 F1 91.2(2) . . ?
F2 P1 F3 90.63(19) . . ?
F2 P1 F4 88.7(2) . . ?
F2 P1 F5 179.0(2) . . ?
F3 P1 F4 89.07(19) . . ?
F3 P1 F5 89.12(18) . . ?
F5 P1 F4 90.4(2) . . ?
F6 P1 F1 91.5(2) . . ?
F6 P1 F2 90.4(2) . . ?
F6 P1 F3 178.1(2) . . ?
F6 P1 F4 89.3(2) . . ?
F6 P1 F5 89.8(2) . . ?
F7 P2 F9 92.0(2) . . ?
F7 P2 F10 166.5(4) . . ?
F7 P2 F11 82.6(4) . . ?
F7 P2 F12 88.1(2) . . ?
F8 P2 F7 101.8(6) . . ?
F8 P2 F9 90.8(3) . . ?
F8 P2 F10 91.7(5) . . ?
F8 P2 F11 175.1(6) . . ?
F8 P2 F12 88.4(4) . . ?
F9 P2 F10 88.1(2) . . ?
F9 P2 F11 91.1(4) . . ?
F9 P2 F12 179.2(3) . . ?
F10 P2 F11 83.9(3) . . ?
F10 P2 F12 92.1(2) . . ?
F12 P2 F11 89.7(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_1d
_database_code_depnum_ccdc_archive 'CCDC 1983240'
loop_
_audit_author_name
_audit_author_address
'David Herbert'
;University of Manitoba
Canada
;
_audit_update_record             
;
2020-02-10 deposited with the CCDC.	2020-04-12 downloaded from the CCDC.
;
_audit_creation_date             2019-03-18
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H17 Cl2 N5 Zn, C2 H3 N'
_chemical_formula_sum            'C25 H20 Cl2 N6 Zn'
_chemical_formula_weight         540.74
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.7284(7)
_cell_length_b                   14.8601(13)
_cell_length_c                   22.4323(19)
_cell_angle_alpha                90
_cell_angle_beta                 97.628(4)
_cell_angle_gamma                90
_cell_volume                     2553.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9127
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.642
_cell_measurement_theta_min      2.659
_shelx_estimated_absorpt_T_max   0.880
_shelx_estimated_absorpt_T_min   0.731
_exptl_absorpt_coefficient_mu    1.196
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1015 before and 0.0767 after correction.
The Ratio of minimum to maximum transmission is 0.7681.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       blocks
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0966
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            66904
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.055
_diffrn_reflns_theta_min         2.659
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8 Quest ECO CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4385
_reflns_number_total             6121
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.854
_refine_diff_density_min         -1.036
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.219
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         6121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0656
_refine_ls_restrained_S_all      1.219
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0190P)²+10.1397P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1380
_refine_ls_wR_factor_ref         0.1495
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C14(H14), C15(H15), C18(H18),
 C19(H19), C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C9(H9A,H9B,H9C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4659(6) 0.4907(3) 0.1927(2) 0.0304(10) Uani 1 1 d . . . . .
C2 C 0.5309(7) 0.5568(4) 0.1512(2) 0.0413(12) Uani 1 1 d . . . . .
H2A H 0.431552 0.586053 0.127148 0.062 Uiso 1 1 calc GR . . . .
H2B H 0.601806 0.525635 0.124555 0.062 Uiso 1 1 calc GR . . . .
H2C H 0.602218 0.602317 0.174665 0.062 Uiso 1 1 calc GR . . . .
C3 C 0.3339(6) 0.5226(3) 0.2317(2) 0.0294(10) Uani 1 1 d . . . . .
C4 C 0.2574(6) 0.6067(4) 0.2273(2) 0.0388(12) Uani 1 1 d . . . . .
H4 H 0.286804 0.648865 0.198416 0.047 Uiso 1 1 calc R . . . .
C5 C 0.1375(7) 0.6288(4) 0.2654(3) 0.0441(13) Uani 1 1 d . . . . .
H5 H 0.081038 0.685675 0.262307 0.053 Uiso 1 1 calc R . . . .
C6 C 0.1007(6) 0.5669(3) 0.3081(2) 0.0364(12) Uani 1 1 d . . . . .
H6 H 0.018594 0.580989 0.334649 0.044 Uiso 1 1 calc R . . . .
C7 C 0.1853(5) 0.4835(3) 0.3118(2) 0.0297(10) Uani 1 1 d . . . . .
C8 C 0.1676(5) 0.4140(3) 0.3580(2) 0.0296(10) Uani 1 1 d . . . . .
C9 C 0.0574(6) 0.4342(4) 0.4061(2) 0.0362(11) Uani 1 1 d . . . . .
H9A H 0.087110 0.493952 0.422941 0.054 Uiso 1 1 calc GR . . . .
H9B H 0.078743 0.388907 0.438020 0.054 Uiso 1 1 calc GR . . . .
H9C H -0.066108 0.432984 0.389083 0.054 Uiso 1 1 calc GR . . . .
C10 C 0.6386(6) 0.3690(3) 0.1677(2) 0.0319(10) Uani 1 1 d . . . . .
C11 C 0.8127(6) 0.3962(4) 0.1782(2) 0.0412(13) Uani 1 1 d . . . . .
H11 H 0.847040 0.443287 0.205901 0.049 Uiso 1 1 calc R . . . .
C12 C 0.9345(7) 0.3542(4) 0.1481(3) 0.0464(14) Uani 1 1 d . . . . .
H12 H 1.053230 0.372533 0.155082 0.056 Uiso 1 1 calc R . . . .
C13 C 0.8848(7) 0.2853(4) 0.1077(2) 0.0407(12) Uani 1 1 d . . . . .
C14 C 0.7115(7) 0.2575(4) 0.0976(2) 0.0418(12) Uani 1 1 d . . . . .
H14 H 0.677436 0.210198 0.070044 0.050 Uiso 1 1 calc R . . . .
C15 C 0.5885(6) 0.2993(4) 0.1281(2) 0.0381(12) Uani 1 1 d . . . . .
H15 H 0.470280 0.280044 0.121843 0.046 Uiso 1 1 calc R . . . .
C16 C 1.0126(7) 0.2397(4) 0.0770(3) 0.0506(15) Uani 1 1 d . . . . .
C17 C 0.2488(6) 0.2688(3) 0.3937(2) 0.0304(10) Uani 1 1 d . . . . .
C18 C 0.0969(6) 0.2180(4) 0.3919(2) 0.0369(12) Uani 1 1 d . . . . .
H18 H -0.003213 0.233101 0.364447 0.044 Uiso 1 1 calc R . . . .
C19 C 0.0922(6) 0.1460(4) 0.4300(3) 0.0446(14) Uani 1 1 d . . . . .
H19 H -0.011152 0.111060 0.428901 0.054 Uiso 1 1 calc R . . . .
C20 C 0.2389(7) 0.1243(4) 0.4699(3) 0.0449(13) Uani 1 1 d . . . . .
C21 C 0.3915(6) 0.1743(4) 0.4711(2) 0.0385(12) Uani 1 1 d . . . . .
H21 H 0.492133 0.158600 0.498199 0.046 Uiso 1 1 calc R . . . .
C22 C 0.3965(6) 0.2465(3) 0.4330(2) 0.0333(11) Uani 1 1 d . . . . .
H22 H 0.500424 0.280851 0.433610 0.040 Uiso 1 1 calc R . . . .
C23 C 0.2344(8) 0.0505(6) 0.5112(4) 0.078(3) Uani 1 1 d . . . . .
Cl1 Cl 0.68198(13) 0.32456(9) 0.32822(5) 0.0360(3) Uani 1 1 d . . . . .
Cl2 Cl 0.28977(15) 0.21585(9) 0.22847(6) 0.0375(3) Uani 1 1 d . . . . .
N1 N 0.5104(5) 0.4080(3) 0.19958(17) 0.0309(9) Uani 1 1 d . . . . .
N2 N 0.2979(4) 0.4626(3) 0.27284(17) 0.0274(8) Uani 1 1 d . . . . .
N3 N 0.2563(4) 0.3420(3) 0.35350(17) 0.0292(8) Uani 1 1 d . . . . .
N4 N 1.1128(7) 0.2024(4) 0.0531(3) 0.0679(16) Uani 1 1 d . . . . .
N5 N 0.2313(8) -0.0068(6) 0.5443(4) 0.143(4) Uani 1 1 d . . . . .
Zn1 Zn 0.41353(6) 0.33572(4) 0.27661(2) 0.02745(15) Uani 1 1 d . . . . .
C24 C 1.4021(8) 0.0382(5) 0.0946(3) 0.0610(18) Uani 1 1 d . . . . .
H24A H 1.320165 0.088867 0.091841 0.092 Uiso 1 1 calc GR . . . .
H24B H 1.520194 0.060728 0.092242 0.092 Uiso 1 1 calc GR . . . .
H24C H 1.399899 0.006895 0.132897 0.092 Uiso 1 1 calc GR . . . .
C25 C 1.3518(8) -0.0235(5) 0.0454(3) 0.0553(16) Uani 1 1 d . . . . .
N6 N 1.3128(8) -0.0729(5) 0.0060(3) 0.0736(17) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.486(7) . ?
C1 C3 1.504(6) . ?
C1 N1 1.280(6) . ?
C3 C4 1.381(7) . ?
C3 N2 1.339(6) . ?
C4 C5 1.380(7) . ?
C5 C6 1.384(8) . ?
C6 C7 1.399(7) . ?
C7 C8 1.481(7) . ?
C7 N2 1.348(6) . ?
C8 C9 1.492(6) . ?
C8 N3 1.281(6) . ?
C10 C11 1.395(7) . ?
C10 C15 1.386(7) . ?
C10 N1 1.421(6) . ?
C11 C12 1.379(7) . ?
C12 C13 1.387(8) . ?
C13 C14 1.392(7) . ?
C13 C16 1.446(7) . ?
C14 C15 1.388(7) . ?
C16 N4 1.142(7) . ?
C17 C18 1.392(6) . ?
C17 C22 1.387(6) . ?
C17 N3 1.419(6) . ?
C18 C19 1.372(7) . ?
C19 C20 1.387(7) . ?
C20 C21 1.391(7) . ?
C20 C23 1.438(9) . ?
C21 C22 1.376(7) . ?
C23 N5 1.132(9) . ?
Cl1 Zn1 2.2437(11) . ?
Cl2 Zn1 2.2316(13) . ?
N1 Zn1 2.245(4) . ?
N2 Zn1 2.084(4) . ?
N3 Zn1 2.240(4) . ?
C24 C25 1.448(10) . ?
C25 N6 1.157(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
C2 C1 C3 117.8(4) . . ?
N1 C1 C2 127.0(5) . . ?
N1 C1 C3 115.1(4) . . ?
C4 C3 C1 124.1(5) . . ?
N2 C3 C1 114.2(4) . . ?
N2 C3 C4 121.7(4) . . ?
C5 C4 C3 119.2(5) . . ?
C4 C5 C6 119.1(5) . . ?
C5 C6 C7 119.5(5) . . ?
C6 C7 C8 125.0(4) . . ?
N2 C7 C6 120.1(5) . . ?
N2 C7 C8 114.9(4) . . ?
C7 C8 C9 118.7(4) . . ?
N3 C8 C7 115.3(4) . . ?
N3 C8 C9 125.9(5) . . ?
C11 C10 N1 121.2(5) . . ?
C15 C10 C11 120.4(5) . . ?
C15 C10 N1 118.3(4) . . ?
C12 C11 C10 119.5(5) . . ?
C11 C12 C13 120.4(5) . . ?
C12 C13 C14 120.2(5) . . ?
C12 C13 C16 120.7(5) . . ?
C14 C13 C16 119.1(5) . . ?
C15 C14 C13 119.6(5) . . ?
C10 C15 C14 119.9(5) . . ?
N4 C16 C13 178.9(7) . . ?
C18 C17 N3 120.2(4) . . ?
C22 C17 C18 120.6(5) . . ?
C22 C17 N3 119.2(4) . . ?
C19 C18 C17 119.8(4) . . ?
C18 C19 C20 119.7(5) . . ?
C19 C20 C21 120.5(5) . . ?
C19 C20 C23 120.4(5) . . ?
C21 C20 C23 119.2(5) . . ?
C22 C21 C20 119.9(5) . . ?
C21 C22 C17 119.5(4) . . ?
N5 C23 C20 179.1(11) . . ?
C1 N1 C10 121.7(4) . . ?
C1 N1 Zn1 116.1(3) . . ?
C10 N1 Zn1 121.3(3) . . ?
C3 N2 C7 120.4(4) . . ?
C3 N2 Zn1 120.2(3) . . ?
C7 N2 Zn1 119.4(3) . . ?
C8 N3 C17 121.5(4) . . ?
C8 N3 Zn1 116.5(3) . . ?
C17 N3 Zn1 121.9(3) . . ?
Cl1 Zn1 N1 93.02(10) . . ?
Cl2 Zn1 Cl1 119.88(5) . . ?
Cl2 Zn1 N1 100.05(11) . . ?
Cl2 Zn1 N3 99.47(11) . . ?
N2 Zn1 Cl1 116.75(10) . . ?
N2 Zn1 Cl2 123.28(10) . . ?
N2 Zn1 N1 73.80(15) . . ?
N2 Zn1 N3 73.72(15) . . ?
N3 Zn1 Cl1 99.49(10) . . ?
N3 Zn1 N1 147.44(15) . . ?
N6 C25 C24 179.5(7) . . ?

_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_1c
_database_code_depnum_ccdc_archive 'CCDC 1983241'
loop_
_audit_author_name
_audit_author_address
'David Herbert'
;University of Manitoba
Canada
;
_audit_update_record             
;
2020-02-10 deposited with the CCDC.	2020-04-12 downloaded from the CCDC.
;
_audit_creation_date             2020-01-24
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H17 Br2 Cl2 N3 Zn, 0.5(C2 H3 N)'
_chemical_formula_sum            'C22 H18.50 Br2 Cl2 N3.50 Zn'
_chemical_formula_weight         627.99
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   12.9613(7)
_cell_length_b                   14.5938(6)
_cell_length_c                   15.1144(7)
_cell_angle_alpha                92.855(2)
_cell_angle_beta                 110.335(2)
_cell_angle_gamma                102.818(2)
_cell_volume                     2588.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9969
_cell_measurement_temperature    151(2)
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      2.64
_shelx_estimated_absorpt_T_max   0.515
_shelx_estimated_absorpt_T_min   0.155
_exptl_absorpt_coefficient_mu    4.257
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.3803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1137 before and 0.0633 after correction.
The Ratio of minimum to maximum transmission is 0.5097.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Rod
_exptl_crystal_F_000             1236
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0702
_diffrn_reflns_av_unetI/netI     0.1025
_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       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            34726
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.721
_diffrn_reflns_theta_min         2.639
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker D8 Quest ECO CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9160
_reflns_number_total             15756
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.609
_refine_diff_density_min         -1.156
_refine_diff_density_rms         0.139
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     555
_refine_ls_number_reflns         15756
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1361
_refine_ls_R_factor_gt           0.0708
_refine_ls_restrained_S_all      1.037
_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)+(0.0093P)²+12.0571P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1345
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C14(H14), C15(H15), C17(H17),
 C18(H18), C20(H20), C21(H21), C25(H25), C26(H26), C27(H27), C32(H32), C33(H33),
  C35(H35), C36(H36), C38(H38), C39(H39), C41(H41), C42(H42)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C9(H9A,H9B,H9C), C23(H23A,H23B,H23C), C30(H30A,H30B,H30C),
 C43(H43A,H43B,H43C)
;
_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 0.35535(7) -0.05628(5) 0.37165(5) 0.05091(18) Uani 1 1 d . . . . .
Br2 Br 0.27368(7) 0.20289(5) 1.17763(5) 0.0562(2) Uani 1 1 d . . . . .
C1 C 0.1962(4) 0.3368(4) 0.4869(4) 0.0268(11) Uani 1 1 d . . . . .
C2 C 0.2054(5) 0.3548(4) 0.3929(4) 0.0353(13) Uani 1 1 d . . . . .
H2A H 0.142012 0.379951 0.355555 0.053 Uiso 1 1 calc GR . . . .
H2B H 0.202579 0.295229 0.358071 0.053 Uiso 1 1 calc GR . . . .
H2C H 0.277594 0.400928 0.403473 0.053 Uiso 1 1 calc GR . . . .
C3 C 0.1696(4) 0.4103(3) 0.5413(4) 0.0247(10) Uani 1 1 d . . . . .
C4 C 0.1523(4) 0.4959(4) 0.5117(4) 0.0323(12) Uani 1 1 d . . . . .
H4 H 0.154850 0.510841 0.451869 0.039 Uiso 1 1 calc R . . . .
C5 C 0.1315(5) 0.5589(4) 0.5700(4) 0.0367(13) Uani 1 1 d . . . . .
H5 H 0.118732 0.617430 0.550082 0.044 Uiso 1 1 calc R . . . .
C6 C 0.1290(4) 0.5377(4) 0.6575(4) 0.0337(13) Uani 1 1 d . . . . .
H6 H 0.114289 0.580322 0.698375 0.040 Uiso 1 1 calc R . . . .
C7 C 0.1492(4) 0.4508(3) 0.6832(4) 0.0264(11) Uani 1 1 d . . . . .
C8 C 0.1581(4) 0.4230(3) 0.7793(4) 0.0289(11) Uani 1 1 d . . . . .
C9 C 0.1427(5) 0.4897(4) 0.8480(4) 0.0353(13) Uani 1 1 d . . . . .
H9A H 0.202038 0.549249 0.863077 0.053 Uiso 1 1 calc GR . . . .
H9B H 0.148193 0.461536 0.906468 0.053 Uiso 1 1 calc GR . . . .
H9C H 0.067741 0.502421 0.819895 0.053 Uiso 1 1 calc GR . . . .
C10 C 0.2416(4) 0.1900(4) 0.4849(4) 0.0277(11) Uani 1 1 d . . . . .
C11 C 0.3506(5) 0.2052(4) 0.4857(4) 0.0380(14) Uani 1 1 d . . . . .
H11 H 0.402581 0.265801 0.510097 0.046 Uiso 1 1 calc R . . . .
C12 C 0.3846(5) 0.1319(4) 0.4508(5) 0.0410(14) Uani 1 1 d . . . . .
H12 H 0.459720 0.141306 0.451240 0.049 Uiso 1 1 calc R . . . .
C13 C 0.3069(5) 0.0455(4) 0.4156(4) 0.0324(12) Uani 1 1 d . . . . .
C14 C 0.1975(5) 0.0288(4) 0.4133(4) 0.0328(12) Uani 1 1 d . . . . .
H14 H 0.145454 -0.031616 0.387840 0.039 Uiso 1 1 calc R . . . .
C15 C 0.1647(5) 0.1022(4) 0.4490(4) 0.0313(12) Uani 1 1 d . . . . .
H15 H 0.089617 0.092230 0.448772 0.038 Uiso 1 1 calc R . . . .
C16 C 0.2009(5) 0.3116(4) 0.8835(4) 0.0295(11) Uani 1 1 d . . . . .
C17 C 0.1185(5) 0.2423(4) 0.8981(5) 0.0417(14) Uani 1 1 d . . . . .
H17 H 0.047436 0.216323 0.847589 0.050 Uiso 1 1 calc R . . . .
C18 C 0.1393(6) 0.2106(4) 0.9857(5) 0.0452(16) Uani 1 1 d . . . . .
H18 H 0.082094 0.164451 0.996455 0.054 Uiso 1 1 calc R . . . .
C19 C 0.2429(5) 0.2465(4) 1.0567(4) 0.0371(13) Uani 1 1 d . . . . .
C20 C 0.3275(5) 0.3143(4) 1.0440(5) 0.0413(14) Uani 1 1 d . . . . .
H20 H 0.399324 0.338152 1.094215 0.050 Uiso 1 1 calc R . . . .
C21 C 0.3057(5) 0.3464(4) 0.9570(4) 0.0392(14) Uani 1 1 d . . . . .
H21 H 0.363039 0.393089 0.947141 0.047 Uiso 1 1 calc R . . . .
Cl1 Cl 0.40126(11) 0.29535(9) 0.74917(10) 0.0338(3) Uani 1 1 d . . . . .
Cl2 Cl 0.10093(11) 0.12413(9) 0.66470(10) 0.0333(3) Uani 1 1 d . . . . .
N1 N 0.2094(3) 0.2632(3) 0.5265(3) 0.0266(9) Uani 1 1 d . . . . .
N2 N 0.1675(3) 0.3899(3) 0.6262(3) 0.0256(9) Uani 1 1 d . . . . .
N3 N 0.1813(4) 0.3434(3) 0.7932(3) 0.0279(9) Uani 1 1 d . . . . .
Zn1 Zn 0.21214(5) 0.26816(4) 0.67526(4) 0.02491(13) Uani 1 1 d . . . . .
Br3 Br 0.17908(7) 0.66813(5) 0.31977(5) 0.05349(19) Uani 1 1 d . . . . .
Br4 Br 0.14237(5) 0.44184(4) 1.14987(4) 0.03787(14) Uani 1 1 d . . . . .
C22 C 0.3236(4) 0.9603(3) 0.7341(4) 0.0230(10) Uani 1 1 d . . . . .
C23 C 0.3445(5) 1.0263(4) 0.6672(4) 0.0302(11) Uani 1 1 d . . . . .
H23A H 0.283156 1.058700 0.646704 0.045 Uiso 1 1 calc GR . . . .
H23B H 0.346590 0.990575 0.611522 0.045 Uiso 1 1 calc GR . . . .
H23C H 0.417407 1.073395 0.699157 0.045 Uiso 1 1 calc GR . . . .
C24 C 0.3464(4) 0.9994(3) 0.8339(4) 0.0232(10) Uani 1 1 d . . . . .
C25 C 0.3847(4) 1.0956(3) 0.8686(4) 0.0285(11) Uani 1 1 d . . . . .
H25 H 0.396160 1.141241 0.827969 0.034 Uiso 1 1 calc R . . . .
C26 C 0.4058(4) 1.1237(4) 0.9629(4) 0.0312(12) Uani 1 1 d . . . . .
H26 H 0.433276 1.189136 0.988208 0.037 Uiso 1 1 calc R . . . .
C27 C 0.3871(4) 1.0567(4) 1.0208(4) 0.0285(11) Uani 1 1 d . . . . .
H27 H 0.401735 1.074927 1.086135 0.034 Uiso 1 1 calc R . . . .
C28 C 0.3460(4) 0.9615(4) 0.9807(4) 0.0250(10) Uani 1 1 d . . . . .
C29 C 0.3192(4) 0.8817(4) 1.0344(4) 0.0268(11) Uani 1 1 d . . . . .
C30 C 0.3352(5) 0.9044(4) 1.1364(4) 0.0343(12) Uani 1 1 d . . . . .
H30A H 0.412127 0.944554 1.171316 0.051 Uiso 1 1 calc GR . . . .
H30B H 0.324619 0.845485 1.164258 0.051 Uiso 1 1 calc GR . . . .
H30C H 0.279214 0.938219 1.140605 0.051 Uiso 1 1 calc GR . . . .
C31 C 0.2633(4) 0.8232(3) 0.6215(4) 0.0260(11) Uani 1 1 d . . . . .
C32 C 0.1640(5) 0.8244(4) 0.5478(4) 0.0312(12) Uani 1 1 d . . . . .
H32 H 0.113317 0.857449 0.558935 0.037 Uiso 1 1 calc R . . . .
C33 C 0.1383(5) 0.7779(4) 0.4581(4) 0.0336(12) Uani 1 1 d . . . . .
H33 H 0.069724 0.777573 0.407412 0.040 Uiso 1 1 calc R . . . .
C34 C 0.2141(5) 0.7321(4) 0.4438(4) 0.0344(13) Uani 1 1 d . . . . .
C35 C 0.3128(5) 0.7283(4) 0.5165(4) 0.0327(12) Uani 1 1 d . . . . .
H35 H 0.362888 0.694648 0.505016 0.039 Uiso 1 1 calc R . . . .
C36 C 0.3370(4) 0.7742(4) 0.6058(4) 0.0305(12) Uani 1 1 d . . . . .
H36 H 0.404280 0.772285 0.656815 0.037 Uiso 1 1 calc R . . . .
C37 C 0.2523(4) 0.7172(3) 1.0294(4) 0.0266(11) Uani 1 1 d . . . . .
C38 C 0.3290(5) 0.6635(4) 1.0636(4) 0.0356(13) Uani 1 1 d . . . . .
H38 H 0.403071 0.682491 1.061684 0.043 Uiso 1 1 calc R . . . .
C39 C 0.2973(5) 0.5814(4) 1.1010(4) 0.0389(14) Uani 1 1 d . . . . .
H39 H 0.349399 0.543844 1.125211 0.047 Uiso 1 1 calc R . . . .
C40 C 0.1886(4) 0.5554(4) 1.1023(4) 0.0276(11) Uani 1 1 d . . . . .
C41 C 0.1122(5) 0.6083(4) 1.0673(4) 0.0320(12) Uani 1 1 d . . . . .
H41 H 0.037691 0.589197 1.068327 0.038 Uiso 1 1 calc R . . . .
C42 C 0.1446(5) 0.6901(4) 1.0302(4) 0.0321(12) Uani 1 1 d . . . . .
H42 H 0.092194 0.727281 1.005498 0.038 Uiso 1 1 calc R . . . .
Cl3 Cl 0.37899(11) 0.69707(10) 0.84034(10) 0.0356(3) Uani 1 1 d . . . . .
Cl4 Cl 0.07592(11) 0.73625(10) 0.76730(11) 0.0367(3) Uani 1 1 d . . . . .
N4 N 0.2895(3) 0.8698(3) 0.7149(3) 0.0246(9) Uani 1 1 d . . . . .
N5 N 0.3267(3) 0.9353(3) 0.8906(3) 0.0223(8) Uani 1 1 d . . . . .
N6 N 0.2840(3) 0.7999(3) 0.9873(3) 0.0275(9) Uani 1 1 d . . . . .
Zn2 Zn 0.26436(5) 0.79246(4) 0.83428(4) 0.02381(13) Uani 1 1 d . . . . .
C43 C 0.0039(7) 0.9660(6) 0.8176(6) 0.067(2) Uani 1 1 d . . . . .
H43A H -0.011547 0.907652 0.774890 0.101 Uiso 1 1 calc GR . . . .
H43B H 0.054527 1.017702 0.802084 0.101 Uiso 1 1 calc GR . . . .
H43C H -0.067824 0.982460 0.809583 0.101 Uiso 1 1 calc GR . . . .
C44 C 0.0577(6) 0.9513(5) 0.9151(6) 0.0476(17) Uani 1 1 d . . . . .
N7 N 0.0998(5) 0.9409(5) 0.9921(5) 0.0573(16) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C13 1.909(6) . ?
Br2 C19 1.905(6) . ?
C1 C2 1.498(7) . ?
C1 C3 1.490(8) . ?
C1 N1 1.271(6) . ?
C3 C4 1.386(7) . ?
C3 N2 1.339(6) . ?
C4 C5 1.375(8) . ?
C5 C6 1.382(8) . ?
C6 C7 1.398(7) . ?
C7 C8 1.501(7) . ?
C7 N2 1.322(7) . ?
C8 C9 1.481(8) . ?
C8 N3 1.273(6) . ?
C10 C11 1.377(7) . ?
C10 C15 1.385(7) . ?
C10 N1 1.422(7) . ?
C11 C12 1.391(8) . ?
C12 C13 1.373(8) . ?
C13 C14 1.373(8) . ?
C14 C15 1.387(8) . ?
C16 C17 1.385(7) . ?
C16 C21 1.388(8) . ?
C16 N3 1.420(7) . ?
C17 C18 1.382(8) . ?
C18 C19 1.363(9) . ?
C19 C20 1.379(8) . ?
C20 C21 1.374(8) . ?
Cl1 Zn1 2.2439(14) . ?
Cl2 Zn1 2.2324(13) . ?
N1 Zn1 2.234(4) . ?
N2 Zn1 2.081(4) . ?
N3 Zn1 2.245(4) . ?
Br3 C34 1.908(6) . ?
Br4 C40 1.898(5) . ?
C22 C23 1.482(7) . ?
C22 C24 1.488(7) . ?
C22 N4 1.279(6) . ?
C24 C25 1.388(7) . ?
C24 N5 1.343(6) . ?
C25 C26 1.378(8) . ?
C26 C27 1.382(7) . ?
C27 C28 1.394(7) . ?
C28 C29 1.498(7) . ?
C28 N5 1.316(6) . ?
C29 C30 1.492(7) . ?
C29 N6 1.261(7) . ?
C31 C32 1.383(7) . ?
C31 C36 1.388(7) . ?
C31 N4 1.428(6) . ?
C32 C33 1.379(8) . ?
C33 C34 1.371(8) . ?
C34 C35 1.381(8) . ?
C35 C36 1.375(8) . ?
C37 C38 1.378(7) . ?
C37 C42 1.368(7) . ?
C37 N6 1.438(6) . ?
C38 C39 1.391(8) . ?
C39 C40 1.382(8) . ?
C40 C41 1.369(7) . ?
C41 C42 1.387(7) . ?
Cl3 Zn2 2.2337(14) . ?
Cl4 Zn2 2.2300(14) . ?
N4 Zn2 2.255(4) . ?
N5 Zn2 2.078(4) . ?
N6 Zn2 2.231(4) . ?
C43 C44 1.446(11) . ?
C44 N7 1.135(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
C3 C1 C2 118.8(4) . . ?
N1 C1 C2 126.0(5) . . ?
N1 C1 C3 115.2(5) . . ?
C4 C3 C1 124.8(5) . . ?
N2 C3 C1 114.7(4) . . ?
N2 C3 C4 120.4(5) . . ?
C5 C4 C3 119.1(5) . . ?
C4 C5 C6 120.5(5) . . ?
C5 C6 C7 117.1(5) . . ?
C6 C7 C8 122.1(5) . . ?
N2 C7 C6 122.1(5) . . ?
N2 C7 C8 115.7(4) . . ?
C9 C8 C7 118.4(4) . . ?
N3 C8 C7 114.6(5) . . ?
N3 C8 C9 127.0(5) . . ?
C11 C10 C15 120.6(5) . . ?
C11 C10 N1 119.8(5) . . ?
C15 C10 N1 119.5(5) . . ?
C10 C11 C12 120.0(5) . . ?
C13 C12 C11 118.3(5) . . ?
C12 C13 Br1 118.2(4) . . ?
C14 C13 Br1 119.0(4) . . ?
C14 C13 C12 122.7(5) . . ?
C13 C14 C15 118.5(5) . . ?
C10 C15 C14 119.8(5) . . ?
C17 C16 C21 119.1(5) . . ?
C17 C16 N3 120.8(5) . . ?
C21 C16 N3 120.0(5) . . ?
C18 C17 C16 120.3(6) . . ?
C19 C18 C17 119.2(6) . . ?
C18 C19 Br2 119.8(5) . . ?
C18 C19 C20 122.0(6) . . ?
C20 C19 Br2 118.2(5) . . ?
C21 C20 C19 118.5(6) . . ?
C20 C21 C16 120.9(5) . . ?
C1 N1 C10 121.0(4) . . ?
C1 N1 Zn1 116.3(4) . . ?
C10 N1 Zn1 121.7(3) . . ?
C3 N2 Zn1 119.4(3) . . ?
C7 N2 C3 120.8(4) . . ?
C7 N2 Zn1 119.5(3) . . ?
C8 N3 C16 120.6(5) . . ?
C8 N3 Zn1 116.2(4) . . ?
C16 N3 Zn1 122.6(3) . . ?
Cl1 Zn1 N3 96.55(12) . . ?
Cl2 Zn1 Cl1 119.41(5) . . ?
Cl2 Zn1 N1 99.72(11) . . ?
Cl2 Zn1 N3 99.01(11) . . ?
N1 Zn1 Cl1 96.97(11) . . ?
N1 Zn1 N3 147.58(15) . . ?
N2 Zn1 Cl1 111.14(12) . . ?
N2 Zn1 Cl2 129.44(12) . . ?
N2 Zn1 N1 73.75(16) . . ?
N2 Zn1 N3 73.90(16) . . ?
C23 C22 C24 119.1(4) . . ?
N4 C22 C23 125.6(5) . . ?
N4 C22 C24 115.2(4) . . ?
C25 C24 C22 123.8(4) . . ?
N5 C24 C22 115.7(4) . . ?
N5 C24 C25 120.5(5) . . ?
C26 C25 C24 118.9(5) . . ?
C25 C26 C27 120.0(5) . . ?
C26 C27 C28 118.2(5) . . ?
C27 C28 C29 123.8(5) . . ?
N5 C28 C27 121.5(5) . . ?
N5 C28 C29 114.7(4) . . ?
C30 C29 C28 118.8(5) . . ?
N6 C29 C28 115.4(5) . . ?
N6 C29 C30 125.8(5) . . ?
C32 C31 C36 120.0(5) . . ?
C32 C31 N4 120.6(5) . . ?
C36 C31 N4 119.3(5) . . ?
C33 C32 C31 120.3(5) . . ?
C34 C33 C32 118.5(5) . . ?
C33 C34 Br3 118.6(4) . . ?
C33 C34 C35 122.4(5) . . ?
C35 C34 Br3 118.9(4) . . ?
C36 C35 C34 118.5(5) . . ?
C35 C36 C31 120.2(5) . . ?
C38 C37 N6 119.3(5) . . ?
C42 C37 C38 120.9(5) . . ?
C42 C37 N6 119.6(5) . . ?
C37 C38 C39 119.6(5) . . ?
C40 C39 C38 118.8(5) . . ?
C39 C40 Br4 119.5(4) . . ?
C41 C40 Br4 119.1(4) . . ?
C41 C40 C39 121.4(5) . . ?
C40 C41 C42 119.3(5) . . ?
C37 C42 C41 119.8(5) . . ?
C22 N4 C31 120.9(4) . . ?
C22 N4 Zn2 115.7(3) . . ?
C31 N4 Zn2 123.3(3) . . ?
C24 N5 Zn2 119.1(3) . . ?
C28 N5 C24 121.1(4) . . ?
C28 N5 Zn2 119.8(3) . . ?
C29 N6 C37 121.2(4) . . ?
C29 N6 Zn2 116.2(3) . . ?
C37 N6 Zn2 122.5(3) . . ?
Cl3 Zn2 N4 98.37(11) . . ?
Cl4 Zn2 Cl3 120.52(6) . . ?
Cl4 Zn2 N4 97.51(11) . . ?
Cl4 Zn2 N6 99.19(11) . . ?
N5 Zn2 Cl3 122.22(12) . . ?
N5 Zn2 Cl4 117.26(12) . . ?
N5 Zn2 N4 74.19(15) . . ?
N5 Zn2 N6 73.81(15) . . ?
N6 Zn2 Cl3 96.45(12) . . ?
N6 Zn2 N4 147.90(15) . . ?
N7 C44 C43 179.2(8) . . ?

_platon_squeeze_details          ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.500 0.500 249 101 ' '

_platon_squeeze_void_probe_radius 1.20
_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_3c
_database_code_depnum_ccdc_archive 'CCDC 1983242'
loop_
_audit_author_name
_audit_author_address
'David Herbert'
;University of Manitoba
Canada
;
_audit_update_record             
;
2020-02-10 deposited with the CCDC.	2020-04-12 downloaded from the CCDC.
;
_audit_creation_date             2019-08-19
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C42 H34 Br4 Fe N6, C2 H3 N, 2(F6 P)'
_chemical_formula_sum            'C44 H37 Br4 F12 Fe N7 P2'
_chemical_formula_weight         1329.23
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 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'

_cell_length_a                   17.9244(7)
_cell_length_b                   17.5570(7)
_cell_length_c                   15.9880(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.194(2)
_cell_angle_gamma                90
_cell_volume                     4917.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9846
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.58
_cell_measurement_theta_min      2.66
_shelx_estimated_absorpt_T_max   0.510
_shelx_estimated_absorpt_T_min   0.341
_exptl_absorpt_coefficient_mu    3.708
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6058
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1017 before and 0.0825 after correction.
The Ratio of minimum to maximum transmission is 0.8120.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.795
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2616
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            79707
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.617
_diffrn_reflns_theta_min         2.320
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Quest ECO CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.977
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                12406
_reflns_number_total             14968
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.047(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     637
_refine_ls_number_reflns         14968
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.048
_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)+3.7254P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0547
_refine_ls_wR_factor_ref         0.0590
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.953(5)
 0.047(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C14(H14), C15(H15), C17(H17),
 C18(H18), C20(H20), C21(H21), C25(H25), C26(H26), C27(H27), C32(H32), C33(H33),
  C35(H35), C36(H36), C38(H38), C39(H39), C41(H41), C42(H42)
3.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C9(H9A,H9B,H9C), C23(H23A,H23B,H23C), C30(H30A,H30B,H30C),
 C43(H43A,H43B,H43C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.12670(2) 0.64674(3) 0.69800(3) 0.03782(11) Uani 1 1 d . . . . .
Br2 Br 0.40271(2) 0.89494(2) 0.11497(3) 0.03106(10) Uani 1 1 d . . . . .
Br3 Br 0.67380(2) 0.33653(2) 0.58740(3) 0.03567(11) Uani 1 1 d . . . . .
Br4 Br 0.63732(3) 0.97887(3) 0.87311(3) 0.03890(11) Uani 1 1 d . . . . .
C1 C 0.5056(2) 0.6197(2) 0.6848(3) 0.0230(8) Uani 1 1 d . . . . .
C2 C 0.4989(2) 0.5678(3) 0.7566(3) 0.0321(10) Uani 1 1 d . . . . .
H2A H 0.528804 0.521520 0.753456 0.048 Uiso 1 1 calc GR . . . .
H2B H 0.445191 0.554076 0.752254 0.048 Uiso 1 1 calc GR . . . .
H2C H 0.518226 0.593501 0.811256 0.048 Uiso 1 1 calc GR . . . .
C3 C 0.5797(2) 0.6331(2) 0.6630(2) 0.0210(8) Uani 1 1 d . . . . .
C4 C 0.6506(2) 0.6046(2) 0.7036(3) 0.0253(8) Uani 1 1 d . . . . .
H4 H 0.655483 0.573878 0.753435 0.030 Uiso 1 1 calc R . . . .
C5 C 0.7135(2) 0.6217(2) 0.6703(3) 0.0277(9) Uani 1 1 d . . . . .
H5 H 0.762391 0.603416 0.698002 0.033 Uiso 1 1 calc R . . . .
C6 C 0.7062(2) 0.6650(2) 0.5970(3) 0.0251(8) Uani 1 1 d . . . . .
H6 H 0.749589 0.676664 0.573956 0.030 Uiso 1 1 calc R . . . .
C7 C 0.63414(19) 0.6912(2) 0.5575(2) 0.0198(7) Uani 1 1 d . . . . .
C8 C 0.6107(2) 0.7301(2) 0.4752(2) 0.0189(7) Uani 1 1 d . . . . .
C9 C 0.6662(2) 0.7486(3) 0.4202(3) 0.0263(9) Uani 1 1 d . . . . .
H9A H 0.718151 0.748420 0.455130 0.039 Uiso 1 1 calc GR . . . .
H9B H 0.654584 0.799062 0.394535 0.039 Uiso 1 1 calc GR . . . .
H9C H 0.662141 0.710377 0.374734 0.039 Uiso 1 1 calc GR . . . .
C10 C 0.3732(2) 0.6496(2) 0.6493(2) 0.0194(7) Uani 1 1 d . . . . .
C11 C 0.3575(2) 0.6860(3) 0.7200(3) 0.0308(9) Uani 1 1 d . . . . .
H11 H 0.397376 0.711018 0.758898 0.037 Uiso 1 1 calc R . . . .
C12 C 0.2839(2) 0.6867(3) 0.7350(3) 0.0335(10) Uani 1 1 d . . . . .
H12 H 0.272999 0.712167 0.783477 0.040 Uiso 1 1 calc R . . . .
C13 C 0.2269(2) 0.6495(2) 0.6781(3) 0.0241(8) Uani 1 1 d . . . . .
C14 C 0.2419(2) 0.6129(2) 0.6074(3) 0.0276(9) Uani 1 1 d . . . . .
H14 H 0.202351 0.587094 0.568935 0.033 Uiso 1 1 calc R . . . .
C15 C 0.3155(2) 0.6140(2) 0.5929(3) 0.0247(8) Uani 1 1 d . . . . .
H15 H 0.325952 0.589906 0.543480 0.030 Uiso 1 1 calc R . . . .
C16 C 0.5053(2) 0.7777(2) 0.3737(2) 0.0179(7) Uani 1 1 d . . . . .
C17 C 0.4860(2) 0.7347(2) 0.3000(2) 0.0230(8) Uani 1 1 d . . . . .
H17 H 0.494565 0.681230 0.302125 0.028 Uiso 1 1 calc R . . . .
C18 C 0.4539(2) 0.7694(2) 0.2228(3) 0.0245(8) Uani 1 1 d . . . . .
H18 H 0.440574 0.740358 0.171688 0.029 Uiso 1 1 calc R . . . .
C19 C 0.4419(2) 0.8472(2) 0.2219(2) 0.0216(8) Uani 1 1 d . . . . .
C20 C 0.4590(2) 0.8905(2) 0.2949(3) 0.0271(9) Uani 1 1 d . . . . .
H20 H 0.449099 0.943712 0.292689 0.032 Uiso 1 1 calc R . . . .
C21 C 0.4909(2) 0.8554(2) 0.3719(3) 0.0270(9) Uani 1 1 d . . . . .
H21 H 0.502890 0.884444 0.423166 0.032 Uiso 1 1 calc R . . . .
C22 C 0.3958(2) 0.5947(2) 0.4124(2) 0.0205(8) Uani 1 1 d . . . . .
C23 C 0.3673(2) 0.5249(2) 0.3633(3) 0.0275(9) Uani 1 1 d . . . . .
H23A H 0.318563 0.509693 0.376677 0.041 Uiso 1 1 calc GR . . . .
H23B H 0.404578 0.483757 0.379059 0.041 Uiso 1 1 calc GR . . . .
H23C H 0.360091 0.535317 0.301915 0.041 Uiso 1 1 calc GR . . . .
C24 C 0.3486(2) 0.6636(2) 0.4033(2) 0.0206(7) Uani 1 1 d . . . . .
C25 C 0.2785(2) 0.6748(2) 0.3483(3) 0.0267(8) Uani 1 1 d . . . . .
H25 H 0.256418 0.636302 0.309064 0.032 Uiso 1 1 calc R . . . .
C26 C 0.2417(2) 0.7435(2) 0.3519(3) 0.0303(9) Uani 1 1 d . . . . .
H26 H 0.193743 0.752369 0.314695 0.036 Uiso 1 1 calc R . . . .
C27 C 0.2740(2) 0.7995(2) 0.4093(3) 0.0283(9) Uani 1 1 d . . . . .
H27 H 0.248836 0.846839 0.411527 0.034 Uiso 1 1 calc R . . . .
C28 C 0.3439(2) 0.7849(2) 0.4634(2) 0.0208(8) Uani 1 1 d . . . . .
C29 C 0.3880(2) 0.8344(2) 0.5302(3) 0.0214(8) Uani 1 1 d . . . . .
C30 C 0.3605(3) 0.9122(2) 0.5435(3) 0.0334(10) Uani 1 1 d . . . . .
H30A H 0.332243 0.932560 0.488854 0.050 Uiso 1 1 calc GR . . . .
H30B H 0.404196 0.945208 0.565971 0.050 Uiso 1 1 calc GR . . . .
H30C H 0.326837 0.910161 0.584420 0.050 Uiso 1 1 calc GR . . . .
C31 C 0.5094(2) 0.5377(2) 0.4915(2) 0.0186(7) Uani 1 1 d . . . . .
C32 C 0.4906(2) 0.4838(2) 0.5468(3) 0.0257(8) Uani 1 1 d . . . . .
H32 H 0.443961 0.488072 0.565691 0.031 Uiso 1 1 calc R . . . .
C33 C 0.5395(2) 0.4238(2) 0.5747(3) 0.0274(9) Uani 1 1 d . . . . .
H33 H 0.526579 0.386408 0.612130 0.033 Uiso 1 1 calc R . . . .
C34 C 0.6076(2) 0.4190(2) 0.5473(3) 0.0241(8) Uani 1 1 d . . . . .
C35 C 0.6271(2) 0.4723(2) 0.4920(3) 0.0247(8) Uani 1 1 d . . . . .
H35 H 0.673886 0.467942 0.473418 0.030 Uiso 1 1 calc R . . . .
C36 C 0.5776(2) 0.5321(2) 0.4640(3) 0.0217(8) Uani 1 1 d . . . . .
H36 H 0.590447 0.569186 0.426162 0.026 Uiso 1 1 calc R . . . .
C37 C 0.4953(2) 0.8444(2) 0.6428(2) 0.0198(7) Uani 1 1 d . . . . .
C38 C 0.4643(2) 0.8607(2) 0.7128(3) 0.0265(9) Uani 1 1 d . . . . .
H38 H 0.413910 0.844467 0.713842 0.032 Uiso 1 1 calc R . . . .
C39 C 0.5065(2) 0.9010(2) 0.7817(3) 0.0289(9) Uani 1 1 d . . . . .
H39 H 0.485420 0.912431 0.829963 0.035 Uiso 1 1 calc R . . . .
C40 C 0.5794(2) 0.9240(2) 0.7788(3) 0.0268(8) Uani 1 1 d . . . . .
C41 C 0.6107(2) 0.9090(2) 0.7088(3) 0.0284(9) Uani 1 1 d . . . . .
H41 H 0.660350 0.926882 0.707119 0.034 Uiso 1 1 calc R . . . .
C42 C 0.5689(2) 0.8677(2) 0.6409(3) 0.0242(8) Uani 1 1 d . . . . .
H42 H 0.590544 0.855475 0.593285 0.029 Uiso 1 1 calc R . . . .
Fe1 Fe 0.47514(3) 0.70100(3) 0.53088(3) 0.01595(10) Uani 1 1 d . . . . .
N1 N 0.44862(17) 0.65182(17) 0.63255(19) 0.0181(6) Uani 1 1 d . . . . .
N2 N 0.57295(16) 0.67693(17) 0.59266(19) 0.0170(6) Uani 1 1 d . . . . .
N3 N 0.53765(16) 0.74165(16) 0.45367(19) 0.0168(6) Uani 1 1 d . . . . .
N4 N 0.45954(16) 0.60184(17) 0.46829(19) 0.0180(6) Uani 1 1 d . . . . .
N5 N 0.37959(16) 0.71759(17) 0.45992(19) 0.0183(6) Uani 1 1 d . . . . .
N6 N 0.45106(16) 0.80375(17) 0.57098(19) 0.0178(6) Uani 1 1 d . . . . .
C43 C 0.4850(4) 0.7742(4) 0.9721(4) 0.0705(19) Uani 1 1 d . . . . .
H43A H 0.442754 0.805613 0.941519 0.106 Uiso 1 1 calc GR . . . .
H43B H 0.519149 0.805409 1.014481 0.106 Uiso 1 1 calc GR . . . .
H43C H 0.464643 0.732266 1.001075 0.106 Uiso 1 1 calc GR . . . .
C44 C 0.5273(3) 0.7431(3) 0.9112(4) 0.0472(13) Uani 1 1 d . . . . .
N7 N 0.5589(3) 0.7190(3) 0.8630(3) 0.0545(12) Uani 1 1 d . . . . .
F1 F 0.76982(17) 0.41852(17) 0.93780(17) 0.0473(7) Uani 1 1 d . . . . .
F2 F 0.76500(16) 0.52201(14) 0.85436(17) 0.0436(7) Uani 1 1 d . . . . .
F3 F 0.70158(17) 0.4159(2) 0.8025(2) 0.0569(8) Uani 1 1 d . . . . .
F4 F 0.80645(19) 0.45176(19) 0.75543(18) 0.0561(8) Uani 1 1 d . . . . .
F5 F 0.8103(2) 0.34790(16) 0.8387(2) 0.0625(9) Uani 1 1 d . . . . .
F6 F 0.87401(15) 0.45410(17) 0.8915(2) 0.0478(7) Uani 1 1 d . . . . .
P1 P 0.78770(6) 0.43442(6) 0.84596(7) 0.0277(2) Uani 1 1 d . . . . .
F7 F 0.29075(19) 0.68207(16) 0.1659(2) 0.0562(8) Uani 1 1 d . . . . .
F8 F 0.27451(16) 0.55477(16) 0.15888(18) 0.0425(6) Uani 1 1 d . . . . .
F9 F 0.21403(15) 0.62900(18) 0.0503(2) 0.0541(8) Uani 1 1 d . . . . .
F10 F 0.32863(16) 0.68043(16) 0.0404(2) 0.0486(7) Uani 1 1 d . . . . .
F11 F 0.31067(15) 0.55298(16) 0.03173(17) 0.0412(6) Uani 1 1 d . . . . .
F12 F 0.38765(14) 0.60502(16) 0.14861(17) 0.0408(6) Uani 1 1 d . . . . .
P2 P 0.30073(6) 0.61757(7) 0.09874(8) 0.0316(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C13 1.890(4) . ?
Br2 C19 1.900(4) . ?
Br3 C34 1.897(4) . ?
Br4 C40 1.902(4) . ?
C1 C2 1.491(5) . ?
C1 C3 1.462(5) . ?
C1 N1 1.303(5) . ?
C3 C4 1.391(5) . ?
C3 N2 1.347(5) . ?
C4 C5 1.379(6) . ?
C5 C6 1.379(6) . ?
C6 C7 1.391(5) . ?
C7 C8 1.463(5) . ?
C7 N2 1.357(4) . ?
C8 C9 1.496(5) . ?
C8 N3 1.298(4) . ?
C10 C11 1.379(6) . ?
C10 C15 1.371(5) . ?
C10 N1 1.433(4) . ?
C11 C12 1.390(6) . ?
C12 C13 1.379(6) . ?
C13 C14 1.376(6) . ?
C14 C15 1.385(5) . ?
C16 C17 1.382(5) . ?
C16 C21 1.387(5) . ?
C16 N3 1.435(5) . ?
C17 C18 1.387(5) . ?
C18 C19 1.382(5) . ?
C19 C20 1.372(6) . ?
C20 C21 1.389(6) . ?
C22 C23 1.485(6) . ?
C22 C24 1.465(5) . ?
C22 N4 1.299(5) . ?
C24 C25 1.387(5) . ?
C24 N5 1.347(5) . ?
C25 C26 1.381(6) . ?
C26 C27 1.385(6) . ?
C27 C28 1.387(5) . ?
C28 C29 1.471(6) . ?
C28 N5 1.351(5) . ?
C29 C30 1.482(6) . ?
C29 N6 1.297(5) . ?
C31 C32 1.384(5) . ?
C31 C36 1.387(5) . ?
C31 N4 1.437(5) . ?
C32 C33 1.383(6) . ?
C33 C34 1.383(5) . ?
C34 C35 1.381(6) . ?
C35 C36 1.386(5) . ?
C37 C38 1.381(5) . ?
C37 C42 1.387(5) . ?
C37 N6 1.439(5) . ?
C38 C39 1.391(6) . ?
C39 C40 1.378(6) . ?
C40 C41 1.378(6) . ?
C41 C42 1.386(6) . ?
Fe1 N1 1.985(3) . ?
Fe1 N2 1.870(3) . ?
Fe1 N3 1.968(3) . ?
Fe1 N4 1.998(3) . ?
Fe1 N5 1.867(3) . ?
Fe1 N6 1.992(3) . ?
C43 C44 1.460(9) . ?
C44 N7 1.130(7) . ?
F1 P1 1.592(3) . ?
F2 P1 1.604(3) . ?
F3 P1 1.587(3) . ?
F4 P1 1.583(3) . ?
F5 P1 1.583(3) . ?
F6 P1 1.602(3) . ?
F7 P2 1.597(3) . ?
F8 P2 1.597(3) . ?
F9 P2 1.596(3) . ?
F10 P2 1.592(3) . ?
F11 P2 1.596(3) . ?
F12 P2 1.608(3) . ?

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
C3 C1 C2 120.5(3) . . ?
N1 C1 C2 125.3(3) . . ?
N1 C1 C3 114.0(3) . . ?
C4 C3 C1 128.1(3) . . ?
N2 C3 C1 111.4(3) . . ?
N2 C3 C4 120.5(3) . . ?
C5 C4 C3 118.8(4) . . ?
C6 C5 C4 120.7(4) . . ?
C5 C6 C7 118.7(3) . . ?
C6 C7 C8 128.7(3) . . ?
N2 C7 C6 120.4(3) . . ?
N2 C7 C8 110.8(3) . . ?
C7 C8 C9 122.0(3) . . ?
N3 C8 C7 113.2(3) . . ?
N3 C8 C9 124.7(3) . . ?
C11 C10 N1 120.3(3) . . ?
C15 C10 C11 119.6(4) . . ?
C15 C10 N1 120.0(3) . . ?
C10 C11 C12 120.7(4) . . ?
C13 C12 C11 118.7(4) . . ?
C12 C13 Br1 119.9(3) . . ?
C14 C13 Br1 118.9(3) . . ?
C14 C13 C12 121.1(4) . . ?
C13 C14 C15 119.3(4) . . ?
C10 C15 C14 120.6(4) . . ?
C17 C16 C21 120.6(3) . . ?
C17 C16 N3 120.0(3) . . ?
C21 C16 N3 119.4(3) . . ?
C16 C17 C18 120.0(4) . . ?
C19 C18 C17 118.6(4) . . ?
C18 C19 Br2 118.2(3) . . ?
C20 C19 Br2 119.6(3) . . ?
C20 C19 C18 122.1(3) . . ?
C19 C20 C21 119.0(4) . . ?
C16 C21 C20 119.6(4) . . ?
C24 C22 C23 120.1(3) . . ?
N4 C22 C23 126.7(3) . . ?
N4 C22 C24 113.2(3) . . ?
C25 C24 C22 127.4(4) . . ?
N5 C24 C22 111.5(3) . . ?
N5 C24 C25 121.0(3) . . ?
C26 C25 C24 118.3(4) . . ?
C25 C26 C27 120.8(4) . . ?
C26 C27 C28 118.5(4) . . ?
C27 C28 C29 128.3(4) . . ?
N5 C28 C27 120.6(4) . . ?
N5 C28 C29 111.1(3) . . ?
C28 C29 C30 120.3(3) . . ?
N6 C29 C28 113.5(3) . . ?
N6 C29 C30 126.2(4) . . ?
C32 C31 C36 120.2(3) . . ?
C32 C31 N4 118.6(3) . . ?
C36 C31 N4 121.0(3) . . ?
C33 C32 C31 120.2(4) . . ?
C32 C33 C34 119.1(4) . . ?
C33 C34 Br3 118.0(3) . . ?
C35 C34 Br3 120.5(3) . . ?
C35 C34 C33 121.4(4) . . ?
C34 C35 C36 119.2(4) . . ?
C35 C36 C31 119.9(4) . . ?
C38 C37 C42 120.2(4) . . ?
C38 C37 N6 120.0(3) . . ?
C42 C37 N6 119.7(3) . . ?
C37 C38 C39 120.1(4) . . ?
C40 C39 C38 119.0(4) . . ?
C39 C40 Br4 119.0(3) . . ?
C39 C40 C41 121.5(4) . . ?
C41 C40 Br4 119.5(3) . . ?
C40 C41 C42 119.4(4) . . ?
C41 C42 C37 119.8(4) . . ?
N1 Fe1 N4 89.93(12) . . ?
N1 Fe1 N6 91.42(12) . . ?
N2 Fe1 N1 80.16(12) . . ?
N2 Fe1 N3 79.56(12) . . ?
N2 Fe1 N4 94.82(12) . . ?
N2 Fe1 N6 106.10(13) . . ?
N3 Fe1 N1 159.71(12) . . ?
N3 Fe1 N4 92.28(12) . . ?
N3 Fe1 N6 93.69(12) . . ?
N5 Fe1 N1 102.58(13) . . ?
N5 Fe1 N2 173.65(14) . . ?
N5 Fe1 N3 97.65(12) . . ?
N5 Fe1 N4 79.52(13) . . ?
N5 Fe1 N6 79.68(13) . . ?
N6 Fe1 N4 158.95(12) . . ?
C1 N1 C10 120.7(3) . . ?
C1 N1 Fe1 115.0(2) . . ?
C10 N1 Fe1 124.3(2) . . ?
C3 N2 C7 120.8(3) . . ?
C3 N2 Fe1 118.7(2) . . ?
C7 N2 Fe1 119.3(2) . . ?
C8 N3 C16 120.0(3) . . ?
C8 N3 Fe1 117.0(2) . . ?
C16 N3 Fe1 122.9(2) . . ?
C22 N4 C31 120.7(3) . . ?
C22 N4 Fe1 116.0(2) . . ?
C31 N4 Fe1 122.7(2) . . ?
C24 N5 C28 120.8(3) . . ?
C24 N5 Fe1 119.6(2) . . ?
C28 N5 Fe1 119.6(3) . . ?
C29 N6 C37 118.1(3) . . ?
C29 N6 Fe1 116.0(3) . . ?
C37 N6 Fe1 125.8(2) . . ?
N7 C44 C43 178.8(6) . . ?
F1 P1 F2 89.25(16) . . ?
F1 P1 F6 88.99(16) . . ?
F3 P1 F1 90.07(17) . . ?
F3 P1 F2 89.60(17) . . ?
F3 P1 F6 178.77(18) . . ?
F4 P1 F1 178.80(19) . . ?
F4 P1 F2 89.93(17) . . ?
F4 P1 F3 90.80(18) . . ?
F4 P1 F6 90.13(18) . . ?
F5 P1 F1 90.20(18) . . ?
F5 P1 F2 179.39(19) . . ?
F5 P1 F3 90.66(19) . . ?
F5 P1 F4 90.61(19) . . ?
F5 P1 F6 90.14(18) . . ?
F6 P1 F2 89.59(16) . . ?
F7 P2 F8 89.75(17) . . ?
F7 P2 F12 89.89(17) . . ?
F8 P2 F12 89.11(16) . . ?
F9 P2 F7 90.08(19) . . ?
F9 P2 F8 89.93(16) . . ?
F9 P2 F12 179.04(18) . . ?
F10 P2 F7 89.77(17) . . ?
F10 P2 F8 178.68(18) . . ?
F10 P2 F9 91.30(16) . . ?
F10 P2 F11 90.34(16) . . ?
F10 P2 F12 89.66(16) . . ?
F11 P2 F7 179.9(2) . . ?
F11 P2 F8 90.13(16) . . ?
F11 P2 F9 89.93(17) . . ?
F11 P2 F12 90.09(14) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.953(5)
2 0.047(5)

