# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_EN17_0m
_database_code_depnum_ccdc_archive 'CCDC 1941363'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller '
;Purdue University
United States of America
;
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H21 Cl2 Fe N3'
_chemical_formula_weight         382.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   10.6209(4)
_cell_length_b                   11.3090(4)
_cell_length_c                   15.1998(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.3000(16)
_cell_angle_gamma                90
_cell_volume                     1806.55(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9617
_cell_measurement_theta_min      5.7471
_cell_measurement_theta_max      80.2604

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    9.399
_shelx_estimated_absorpt_T_min   0.137
_shelx_estimated_absorpt_T_max   0.232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3826
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16963
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         5.747
_diffrn_reflns_theta_max         80.686
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3805
_reflns_number_gt                3456
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Apex3 v2017.3-0 (Bruker, 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev937 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0787P)²+0.8564P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0099(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3805
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1366
_refine_ls_wR_factor_gt          0.1334
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_restrained_S_all      1.177
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.4506(3) 0.2688(2) 0.33112(19) 0.0280(6) Uani 1 1 d . . . . .
H1A H 0.482983 0.264561 0.273995 0.042 Uiso 1 1 calc R U . . .
H1B H 0.517770 0.298396 0.376867 0.042 Uiso 1 1 calc R U . . .
H1C H 0.377515 0.322528 0.325864 0.042 Uiso 1 1 calc R U . . .
C2 C 0.4105(2) 0.1483(2) 0.35651(16) 0.0187(5) Uani 1 1 d . . . . .
C3 C 0.2857(3) 0.1234(2) 0.36790(17) 0.0225(6) Uani 1 1 d . . . . .
H3 H 0.223022 0.183959 0.360021 0.027 Uiso 1 1 calc R U . . .
C4 C 0.2530(3) 0.0105(2) 0.39072(18) 0.0238(6) Uani 1 1 d . . . . .
H4 H 0.168233 -0.006927 0.399617 0.029 Uiso 1 1 calc R U . . .
C5 C 0.3449(3) -0.0772(2) 0.40048(18) 0.0209(6) Uani 1 1 d . . . . .
H5 H 0.324390 -0.155946 0.414836 0.025 Uiso 1 1 calc R U . . .
C6 C 0.4677(2) -0.0468(2) 0.38875(15) 0.0146(5) Uani 1 1 d . . . . .
C7 C 0.5732(2) -0.1317(2) 0.40021(15) 0.0139(5) Uani 1 1 d . . . . .
C8 C 0.5792(2) -0.2514(2) 0.42182(16) 0.0164(5) Uani 1 1 d . . . . .
H8 H 0.510782 -0.300383 0.433293 0.020 Uiso 1 1 calc R U . . .
C9 C 0.7045(2) -0.2847(2) 0.42325(16) 0.0163(5) Uani 1 1 d . . . . .
C10 C 0.7635(3) -0.4057(2) 0.44276(18) 0.0199(5) Uani 1 1 d . . . . .
C11 C 0.6561(3) -0.4921(2) 0.4555(2) 0.0292(6) Uani 1 1 d . . . . .
H11A H 0.593238 -0.493515 0.401530 0.044 Uiso 1 1 calc R U . . .
H11B H 0.614916 -0.466377 0.505956 0.044 Uiso 1 1 calc R U . . .
H11C H 0.691424 -0.571550 0.467160 0.044 Uiso 1 1 calc R U . . .
C12 C 0.8275(3) -0.4508(3) 0.36534(19) 0.0319(7) Uani 1 1 d . . . . .
H12A H 0.766202 -0.449452 0.310611 0.048 Uiso 1 1 calc R U . . .
H12B H 0.857470 -0.531891 0.377616 0.048 Uiso 1 1 calc R U . . .
H12C H 0.900011 -0.399810 0.358182 0.048 Uiso 1 1 calc R U . . .
C13 C 0.8581(3) -0.4051(2) 0.52988(19) 0.0245(6) Uani 1 1 d . . . . .
H13A H 0.894084 -0.484367 0.541022 0.037 Uiso 1 1 calc R U . . .
H13B H 0.813572 -0.381727 0.579317 0.037 Uiso 1 1 calc R U . . .
H13C H 0.926684 -0.348684 0.524664 0.037 Uiso 1 1 calc R U . . .
C14 C 0.9025(2) -0.1637(2) 0.39528(18) 0.0208(5) Uani 1 1 d . . . . .
H14A H 0.954613 -0.228941 0.424767 0.025 Uiso 1 1 calc R U . . .
H14B H 0.930075 -0.089466 0.426825 0.025 Uiso 1 1 calc R U . . .
C15 C 0.9263(3) -0.1544(2) 0.30051(19) 0.0252(6) Uani 1 1 d . . . . .
H15 H 0.870866 -0.106453 0.260797 0.030 Uiso 1 1 calc R U . . .
C16 C 1.0196(3) -0.2089(3) 0.2698(2) 0.0352(7) Uani 1 1 d . . . . .
H16A H 1.076467 -0.257335 0.308163 0.042 Uiso 1 1 calc R U . . .
H16B H 1.030537 -0.199981 0.209246 0.042 Uiso 1 1 calc R U . . .
N1 N 0.5006(2) 0.06419(18) 0.36715(14) 0.0162(4) Uani 1 1 d . . . . .
N2 N 0.6882(2) -0.09163(17) 0.38890(14) 0.0159(4) Uani 1 1 d . . . . .
N3 N 0.7678(2) -0.18542(18) 0.40302(14) 0.0157(4) Uani 1 1 d . . . . .
Cl1 Cl 0.69183(7) 0.09061(6) 0.19635(4) 0.0256(2) Uani 1 1 d . . . . .
Cl2 Cl 0.82672(7) 0.19512(6) 0.43583(4) 0.0285(2) Uani 1 1 d . . . . .
Fe1 Fe 0.69378(4) 0.08198(3) 0.34375(3) 0.01622(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 1.495(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 N1 1.343(3) . ?
C2 C3 1.390(4) . ?
C3 C4 1.381(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(4) . ?
C5 H5 0.9500 . ?
C6 N1 1.356(3) . ?
C6 C7 1.466(3) . ?
C7 N2 1.337(3) . ?
C7 C8 1.393(3) . ?
C8 C9 1.380(4) . ?
C8 H8 0.9500 . ?
C9 N3 1.366(3) . ?
C9 C10 1.516(3) . ?
C10 C12 1.529(4) . ?
C10 C11 1.536(4) . ?
C10 C13 1.542(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 N3 1.473(3) . ?
C14 C15 1.502(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.309(4) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9500 . ?
C16 H16B 0.9500 . ?
N1 Fe1 2.142(2) . ?
N2 N3 1.354(3) . ?
N2 Fe1 2.083(2) . ?
Cl1 Fe1 2.2397(7) . ?
Cl2 Fe1 2.2404(7) . ?

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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 121.1(2) . . ?
N1 C2 C1 116.9(2) . . ?
C3 C2 C1 122.0(2) . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 119.4(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 118.1(2) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
N1 C6 C5 122.7(2) . . ?
N1 C6 C7 114.6(2) . . ?
C5 C6 C7 122.7(2) . . ?
N2 C7 C8 110.3(2) . . ?
N2 C7 C6 117.4(2) . . ?
C8 C7 C6 132.3(2) . . ?
C9 C8 C7 106.3(2) . . ?
C9 C8 H8 126.8 . . ?
C7 C8 H8 126.8 . . ?
N3 C9 C8 106.0(2) . . ?
N3 C9 C10 125.7(2) . . ?
C8 C9 C10 128.3(2) . . ?
C9 C10 C12 111.5(2) . . ?
C9 C10 C11 107.8(2) . . ?
C12 C10 C11 107.9(2) . . ?
C9 C10 C13 111.3(2) . . ?
C12 C10 C13 110.8(2) . . ?
C11 C10 C13 107.4(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C15 112.9(2) . . ?
N3 C14 H14A 109.0 . . ?
C15 C14 H14A 109.0 . . ?
N3 C14 H14B 109.0 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C16 C15 C14 123.4(3) . . ?
C16 C15 H15 118.3 . . ?
C14 C15 H15 118.3 . . ?
C15 C16 H16A 120.0 . . ?
C15 C16 H16B 120.0 . . ?
H16A C16 H16B 120.0 . . ?
C2 N1 C6 118.8(2) . . ?
C2 N1 Fe1 126.63(18) . . ?
C6 N1 Fe1 114.42(16) . . ?
C7 N2 N3 105.98(18) . . ?
C7 N2 Fe1 115.56(16) . . ?
N3 N2 Fe1 138.05(17) . . ?
N2 N3 C9 111.3(2) . . ?
N2 N3 C14 116.6(2) . . ?
C9 N3 C14 132.1(2) . . ?
N2 Fe1 N1 77.49(8) . . ?
N2 Fe1 Cl1 111.96(6) . . ?
N1 Fe1 Cl1 107.43(6) . . ?
N2 Fe1 Cl2 112.19(6) . . ?
N1 Fe1 Cl2 118.84(6) . . ?
Cl1 Fe1 Cl2 120.94(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 0.1(4) . . . . ?
C1 C2 C3 C4 179.5(3) . . . . ?
C2 C3 C4 C5 -1.1(4) . . . . ?
C3 C4 C5 C6 1.4(4) . . . . ?
C4 C5 C6 N1 -0.8(4) . . . . ?
C4 C5 C6 C7 178.1(2) . . . . ?
N1 C6 C7 N2 0.3(3) . . . . ?
C5 C6 C7 N2 -178.7(2) . . . . ?
N1 C6 C7 C8 -179.9(2) . . . . ?
C5 C6 C7 C8 1.1(4) . . . . ?
N2 C7 C8 C9 -0.2(3) . . . . ?
C6 C7 C8 C9 -179.9(2) . . . . ?
C7 C8 C9 N3 0.1(3) . . . . ?
C7 C8 C9 C10 -179.7(2) . . . . ?
N3 C9 C10 C12 -57.9(3) . . . . ?
C8 C9 C10 C12 121.9(3) . . . . ?
N3 C9 C10 C11 -176.1(2) . . . . ?
C8 C9 C10 C11 3.8(4) . . . . ?
N3 C9 C10 C13 66.4(3) . . . . ?
C8 C9 C10 C13 -113.7(3) . . . . ?
N3 C14 C15 C16 -133.6(3) . . . . ?
C3 C2 N1 C6 0.5(4) . . . . ?
C1 C2 N1 C6 -178.9(2) . . . . ?
C3 C2 N1 Fe1 175.38(18) . . . . ?
C1 C2 N1 Fe1 -4.0(3) . . . . ?
C5 C6 N1 C2 -0.1(4) . . . . ?
C7 C6 N1 C2 -179.1(2) . . . . ?
C5 C6 N1 Fe1 -175.62(19) . . . . ?
C7 C6 N1 Fe1 5.4(3) . . . . ?
C8 C7 N2 N3 0.1(3) . . . . ?
C6 C7 N2 N3 179.9(2) . . . . ?
C8 C7 N2 Fe1 174.10(16) . . . . ?
C6 C7 N2 Fe1 -6.1(3) . . . . ?
C7 N2 N3 C9 0.0(3) . . . . ?
Fe1 N2 N3 C9 -171.89(19) . . . . ?
C7 N2 N3 C14 -179.4(2) . . . . ?
Fe1 N2 N3 C14 8.7(4) . . . . ?
C8 C9 N3 N2 -0.1(3) . . . . ?
C10 C9 N3 N2 179.8(2) . . . . ?
C8 C9 N3 C14 179.2(2) . . . . ?
C10 C9 N3 C14 -1.0(4) . . . . ?
C15 C14 N3 N2 -76.4(3) . . . . ?
C15 C14 N3 C9 104.4(3) . . . . ?

_refine_diff_density_max         0.549
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.091


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_EN129_0m
_database_code_depnum_ccdc_archive 'CCDC 1941364'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller '
;Purdue University
United States of America
;
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H21 Br2 N3 Zn, C6 H6'
_chemical_formula_sum            'C22 H27 Br2 N3 Zn'
_chemical_formula_weight         558.66

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   16.0116(4)
_cell_length_b                   14.9760(3)
_cell_length_c                   20.0132(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4798.96(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9040
_cell_measurement_theta_min      5.2124
_cell_measurement_theta_max      80.4199

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_F_000             2240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    5.402
_shelx_estimated_absorpt_T_min   0.370
_shelx_estimated_absorpt_T_max   0.443
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5549
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29510
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.607
_diffrn_reflns_theta_max         80.585
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5163
_reflns_number_gt                4597
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Apex3 v2017.3-0 (Bruker, 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev937 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0368P)²+3.9930P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5163
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0834
_refine_ls_wR_factor_gt          0.0792
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.23421(2) 0.29723(2) 0.40304(2) 0.03139(9) Uani 1 1 d . . . . .
Br2 Br 0.25525(2) 0.13216(2) 0.56172(2) 0.03542(9) Uani 1 1 d . . . . .
Zn1 Zn 0.17073(2) 0.21504(2) 0.48872(2) 0.02203(9) Uani 1 1 d . . . . .
N1 N 0.06482(12) 0.14451(12) 0.45965(10) 0.0215(4) Uani 1 1 d . . . . .
N2 N 0.08126(12) 0.28831(11) 0.53712(10) 0.0204(4) Uani 1 1 d . . . . .
N3 N 0.07446(12) 0.36304(12) 0.57441(10) 0.0214(4) Uani 1 1 d . . . . .
C1 C 0.14252(18) 0.04091(18) 0.39034(17) 0.0398(6) Uani 1 1 d . . . . .
H1A H 0.131464 -0.006628 0.357866 0.060 Uiso 1 1 calc R U . . .
H1B H 0.178411 0.017838 0.426044 0.060 Uiso 1 1 calc R U . . .
H1C H 0.170565 0.090787 0.367950 0.060 Uiso 1 1 calc R U . . .
C2 C 0.06185(16) 0.07252(15) 0.41954(13) 0.0285(5) Uani 1 1 d . . . . .
C3 C -0.01394(17) 0.03056(17) 0.40651(14) 0.0329(5) Uani 1 1 d . . . . .
H3 H -0.015642 -0.020607 0.378491 0.040 Uiso 1 1 calc R U . . .
C4 C -0.08683(16) 0.06336(17) 0.43436(14) 0.0320(5) Uani 1 1 d . . . . .
H4 H -0.138613 0.034476 0.425995 0.038 Uiso 1 1 calc R U . . .
C5 C -0.08378(15) 0.13855(16) 0.47451(13) 0.0275(5) Uani 1 1 d . . . . .
H5 H -0.133184 0.162546 0.493713 0.033 Uiso 1 1 calc R U . . .
C6 C -0.00682(13) 0.17790(14) 0.48595(11) 0.0207(4) Uani 1 1 d . . . . .
C7 C 0.00359(13) 0.25916(14) 0.52673(11) 0.0201(4) Uani 1 1 d . . . . .
C8 C -0.05367(14) 0.31482(15) 0.55727(12) 0.0229(4) Uani 1 1 d . . . . .
H8 H -0.112727 0.308732 0.557095 0.028 Uiso 1 1 calc R U . . .
C9 C -0.00758(14) 0.38128(14) 0.58819(11) 0.0210(4) Uani 1 1 d . . . . .
C10 C -0.03922(15) 0.46075(15) 0.62749(12) 0.0270(5) Uani 1 1 d . . . . .
C11 C -0.13398(17) 0.44997(19) 0.63594(16) 0.0399(6) Uani 1 1 d . . . . .
H11A H -0.160562 0.447947 0.591862 0.060 Uiso 1 1 calc R U . . .
H11B H -0.156129 0.500678 0.661322 0.060 Uiso 1 1 calc R U . . .
H11C H -0.145731 0.394411 0.660043 0.060 Uiso 1 1 calc R U . . .
C12 C -0.02437(19) 0.54720(16) 0.58776(14) 0.0350(6) Uani 1 1 d . . . . .
H12A H -0.049106 0.541383 0.543185 0.052 Uiso 1 1 calc R U . . .
H12B H 0.035788 0.557846 0.583550 0.052 Uiso 1 1 calc R U . . .
H12C H -0.050340 0.597473 0.611241 0.052 Uiso 1 1 calc R U . . .
C13 C 0.00024(19) 0.46606(18) 0.69709(13) 0.0373(6) Uani 1 1 d . . . . .
H13A H 0.060717 0.474278 0.692741 0.056 Uiso 1 1 calc R U . . .
H13B H -0.011074 0.410639 0.721507 0.056 Uiso 1 1 calc R U . . .
H13C H -0.023675 0.516646 0.721556 0.056 Uiso 1 1 calc R U . . .
C14 C 0.15178(15) 0.41107(16) 0.59012(13) 0.0275(5) Uani 1 1 d . . . . .
H14A H 0.137749 0.472812 0.603776 0.033 Uiso 1 1 calc R U . . .
H14B H 0.186656 0.414598 0.549363 0.033 Uiso 1 1 calc R U . . .
C15 C 0.20129(16) 0.36741(18) 0.64477(15) 0.0353(6) Uani 1 1 d . . . . .
H15 H 0.207657 0.304351 0.643762 0.042 Uiso 1 1 calc R U . . .
C16 C 0.2362(2) 0.4118(3) 0.69379(18) 0.0529(8) Uani 1 1 d . . . . .
H16A H 0.230764 0.474903 0.695959 0.063 Uiso 1 1 calc R U . . .
H16B H 0.266910 0.380885 0.727165 0.063 Uiso 1 1 calc R U . . .
C17 C -0.0697(3) 0.2702(2) 0.30416(19) 0.0626(10) Uani 1 1 d . . . . .
H17 H -0.103956 0.257245 0.341681 0.075 Uiso 1 1 calc R U . . .
C18 C 0.0161(3) 0.2609(2) 0.30859(17) 0.0566(10) Uani 1 1 d . . . . .
H18 H 0.040665 0.240868 0.349102 0.068 Uiso 1 1 calc R U . . .
C19 C 0.0655(2) 0.28038(19) 0.25500(17) 0.0482(8) Uani 1 1 d . . . . .
H19 H 0.124462 0.274714 0.258498 0.058 Uiso 1 1 calc R U . . .
C20 C 0.0300(2) 0.30840(19) 0.19556(15) 0.0417(7) Uani 1 1 d . . . . .
H20 H 0.064441 0.321588 0.158217 0.050 Uiso 1 1 calc R U . . .
C21 C -0.0552(2) 0.31712(18) 0.19058(15) 0.0417(7) Uani 1 1 d . . . . .
H21 H -0.079621 0.336079 0.149697 0.050 Uiso 1 1 calc R U . . .
C22 C -0.1054(2) 0.2985(2) 0.24471(19) 0.0527(8) Uani 1 1 d . . . . .
H22 H -0.164230 0.304929 0.241321 0.063 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Zn1 2.3427(4) . ?
Br2 Zn1 2.3466(4) . ?
Zn1 N2 2.0481(19) . ?
Zn1 N1 2.0808(19) . ?
N1 C2 1.345(3) . ?
N1 C6 1.357(3) . ?
N2 C7 1.334(3) . ?
N2 N3 1.350(3) . ?
N3 C9 1.370(3) . ?
N3 C14 1.466(3) . ?
C1 C2 1.495(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.391(4) . ?
C3 C4 1.384(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.475(3) . ?
C7 C8 1.382(3) . ?
C8 C9 1.385(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.514(3) . ?
C10 C13 1.532(4) . ?
C10 C11 1.535(4) . ?
C10 C12 1.538(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.501(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.310(4) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9500 . ?
C16 H16B 0.9500 . ?
C17 C18 1.383(6) . ?
C17 C22 1.386(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.365(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.384(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.374(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.377(5) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Zn1 N1 80.46(7) . . ?
N2 Zn1 Br1 111.60(5) . . ?
N1 Zn1 Br1 114.56(6) . . ?
N2 Zn1 Br2 113.10(5) . . ?
N1 Zn1 Br2 112.06(5) . . ?
Br1 Zn1 Br2 118.905(15) . . ?
C2 N1 C6 119.79(19) . . ?
C2 N1 Zn1 127.05(16) . . ?
C6 N1 Zn1 113.15(14) . . ?
C7 N2 N3 106.39(18) . . ?
C7 N2 Zn1 113.76(14) . . ?
N3 N2 Zn1 139.67(15) . . ?
N2 N3 C9 110.74(18) . . ?
N2 N3 C14 117.21(18) . . ?
C9 N3 C14 131.98(19) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 120.3(2) . . ?
N1 C2 C1 117.2(2) . . ?
C3 C2 C1 122.5(2) . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 119.5(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 118.3(2) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
N1 C6 C5 122.1(2) . . ?
N1 C6 C7 115.03(18) . . ?
C5 C6 C7 122.9(2) . . ?
N2 C7 C8 110.63(19) . . ?
N2 C7 C6 117.48(19) . . ?
C8 C7 C6 131.9(2) . . ?
C7 C8 C9 106.1(2) . . ?
C7 C8 H8 126.9 . . ?
C9 C8 H8 126.9 . . ?
N3 C9 C8 106.12(19) . . ?
N3 C9 C10 125.6(2) . . ?
C8 C9 C10 128.2(2) . . ?
C9 C10 C13 112.0(2) . . ?
C9 C10 C11 107.8(2) . . ?
C13 C10 C11 108.2(2) . . ?
C9 C10 C12 110.0(2) . . ?
C13 C10 C12 111.3(2) . . ?
C11 C10 C12 107.4(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C15 112.9(2) . . ?
N3 C14 H14A 109.0 . . ?
C15 C14 H14A 109.0 . . ?
N3 C14 H14B 109.0 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C16 C15 C14 123.4(3) . . ?
C16 C15 H15 118.3 . . ?
C14 C15 H15 118.3 . . ?
C15 C16 H16A 120.0 . . ?
C15 C16 H16B 120.0 . . ?
H16A C16 H16B 120.0 . . ?
C18 C17 C22 119.7(4) . . ?
C18 C17 H17 120.2 . . ?
C22 C17 H17 120.2 . . ?
C19 C18 C17 120.3(3) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 120.1(3) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C21 C20 C19 120.0(3) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 120.1(3) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C17 119.8(4) . . ?
C21 C22 H22 120.1 . . ?
C17 C22 H22 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N2 N3 C9 0.4(2) . . . . ?
Zn1 N2 N3 C9 174.93(18) . . . . ?
C7 N2 N3 C14 -177.05(19) . . . . ?
Zn1 N2 N3 C14 -2.5(3) . . . . ?
C6 N1 C2 C3 -1.9(4) . . . . ?
Zn1 N1 C2 C3 177.72(19) . . . . ?
C6 N1 C2 C1 178.0(2) . . . . ?
Zn1 N1 C2 C1 -2.4(3) . . . . ?
N1 C2 C3 C4 0.6(4) . . . . ?
C1 C2 C3 C4 -179.3(3) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C2 N1 C6 C5 2.0(3) . . . . ?
Zn1 N1 C6 C5 -177.73(18) . . . . ?
C2 N1 C6 C7 -177.4(2) . . . . ?
Zn1 N1 C6 C7 2.9(2) . . . . ?
C4 C5 C6 N1 -0.6(4) . . . . ?
C4 C5 C6 C7 178.7(2) . . . . ?
N3 N2 C7 C8 -0.1(2) . . . . ?
Zn1 N2 C7 C8 -176.19(15) . . . . ?
N3 N2 C7 C6 179.16(18) . . . . ?
Zn1 N2 C7 C6 3.0(2) . . . . ?
N1 C6 C7 N2 -4.0(3) . . . . ?
C5 C6 C7 N2 176.6(2) . . . . ?
N1 C6 C7 C8 175.0(2) . . . . ?
C5 C6 C7 C8 -4.4(4) . . . . ?
N2 C7 C8 C9 -0.3(3) . . . . ?
C6 C7 C8 C9 -179.4(2) . . . . ?
N2 N3 C9 C8 -0.6(2) . . . . ?
C14 N3 C9 C8 176.4(2) . . . . ?
N2 N3 C9 C10 -178.6(2) . . . . ?
C14 N3 C9 C10 -1.7(4) . . . . ?
C7 C8 C9 N3 0.5(2) . . . . ?
C7 C8 C9 C10 178.5(2) . . . . ?
N3 C9 C10 C13 -56.1(3) . . . . ?
C8 C9 C10 C13 126.3(3) . . . . ?
N3 C9 C10 C11 -175.0(2) . . . . ?
C8 C9 C10 C11 7.4(3) . . . . ?
N3 C9 C10 C12 68.2(3) . . . . ?
C8 C9 C10 C12 -109.4(3) . . . . ?
N2 N3 C14 C15 -77.4(3) . . . . ?
C9 N3 C14 C15 105.8(3) . . . . ?
N3 C14 C15 C16 -136.3(3) . . . . ?
C22 C17 C18 C19 0.7(5) . . . . ?
C17 C18 C19 C20 -0.9(5) . . . . ?
C18 C19 C20 C21 0.4(4) . . . . ?
C19 C20 C21 C22 0.3(4) . . . . ?
C20 C21 C22 C17 -0.5(5) . . . . ?
C18 C17 C22 C21 0.0(5) . . . . ?

_refine_diff_density_max         0.439
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.082


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_JK4179_0m
_database_code_depnum_ccdc_archive 'CCDC 1941365'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller '
;Purdue University
United States of America
;
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H21 Br2 Fe N3'
_chemical_formula_weight         471.03

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.965(2)
_cell_length_b                   11.407(3)
_cell_length_c                   16.929(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.044(4)
_cell_angle_gamma                90
_cell_volume                     1921.6(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    240(2)
_cell_measurement_reflns_used    5146
_cell_measurement_theta_min      2.4095
_cell_measurement_theta_max      29.4205

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.280
_exptl_absorpt_coefficient_mu    4.943
_shelx_estimated_absorpt_T_min   0.220
_shelx_estimated_absorpt_T_max   0.338
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4261
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      240(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS APEXII Kappa CCD diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18297
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.047
_diffrn_reflns_theta_max         30.047
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5525
_reflns_number_gt                3667
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Apex3 v2017.3-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev924 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
The crystal undergoes a destructive phase change upon cooling to around 
200 K (triclinic distortion of the monoclinic cell). Crystals shatter into 
multiple fragments. Data were collected above the phase change temperature 
at 240 K.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0300P)²+0.9850P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5525
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0799
_refine_ls_wR_factor_gt          0.0705
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.22811(3) 0.50408(3) 0.34213(2) 0.05858(11) Uani 1 1 d . . . . .
Br2 Br 0.37495(3) 0.37104(3) 0.13795(2) 0.05242(10) Uani 1 1 d . . . . .
Fe1 Fe 0.22759(4) 0.50008(3) 0.20216(2) 0.03363(9) Uani 1 1 d . . . . .
N1 N 0.0316(2) 0.49448(17) 0.14388(12) 0.0307(4) Uani 1 1 d . . . . .
N2 N 0.2082(2) 0.66671(17) 0.15421(11) 0.0298(4) Uani 1 1 d . . . . .
N3 N 0.27671(19) 0.76948(17) 0.15948(11) 0.0302(4) Uani 1 1 d . . . . .
C1 C -0.0086(3) 0.2961(2) 0.18952(18) 0.0490(7) Uani 1 1 d . . . . .
H1A H -0.072598 0.233017 0.179508 0.073 Uiso 1 1 calc R U . . .
H1B H -0.006232 0.316915 0.245122 0.073 Uiso 1 1 calc R U . . .
H1C H 0.079951 0.270548 0.175618 0.073 Uiso 1 1 calc R U . . .
C2 C -0.0501(3) 0.4003(2) 0.14072(15) 0.0355(6) Uani 1 1 d . . . . .
C3 C -0.1708(3) 0.4034(2) 0.09525(17) 0.0439(7) Uani 1 1 d . . . . .
H3 H -0.227533 0.337487 0.093187 0.053 Uiso 1 1 calc R U . . .
C4 C -0.2066(3) 0.5022(3) 0.05364(18) 0.0494(7) Uani 1 1 d . . . . .
H4 H -0.287152 0.503866 0.022176 0.059 Uiso 1 1 calc R U . . .
C5 C -0.1240(3) 0.6001(2) 0.05784(17) 0.0417(6) Uani 1 1 d . . . . .
H5 H -0.148008 0.669135 0.030261 0.050 Uiso 1 1 calc R U . . .
C6 C -0.0048(2) 0.5933(2) 0.10392(14) 0.0299(5) Uani 1 1 d . . . . .
C7 C 0.0917(2) 0.6904(2) 0.11352(13) 0.0280(5) Uani 1 1 d . . . . .
C8 C 0.0875(2) 0.8082(2) 0.09181(14) 0.0304(5) Uani 1 1 d . . . . .
H8 H 0.017634 0.846527 0.062582 0.037 Uiso 1 1 calc R U . . .
C9 C 0.2072(2) 0.8581(2) 0.12196(14) 0.0294(5) Uani 1 1 d . . . . .
C10 C 0.2516(3) 0.9848(2) 0.12021(15) 0.0333(5) Uani 1 1 d . . . . .
C11 C 0.1472(3) 1.0540(2) 0.06891(16) 0.0407(6) Uani 1 1 d . . . . .
H11A H 0.172467 1.136129 0.068356 0.061 Uiso 1 1 calc R U . . .
H11B H 0.059594 1.046027 0.090656 0.061 Uiso 1 1 calc R U . . .
H11C H 0.143813 1.023536 0.015349 0.061 Uiso 1 1 calc R U . . .
C12 C 0.2558(3) 1.0364(3) 0.20401(17) 0.0520(8) Uani 1 1 d . . . . .
H12A H 0.278617 1.119002 0.201900 0.078 Uiso 1 1 calc R U . . .
H12B H 0.322956 0.995453 0.237129 0.078 Uiso 1 1 calc R U . . .
H12C H 0.168438 1.027478 0.225979 0.078 Uiso 1 1 calc R U . . .
C13 C 0.3872(3) 1.0001(3) 0.0824(2) 0.0524(8) Uani 1 1 d . . . . .
H13A H 0.457211 0.962198 0.115209 0.079 Uiso 1 1 calc R U . . .
H13B H 0.407281 1.082904 0.077892 0.079 Uiso 1 1 calc R U . . .
H13C H 0.382637 0.964675 0.030231 0.079 Uiso 1 1 calc R U . . .
C14 C 0.4143(3) 0.7640(2) 0.19453(17) 0.0439(7) Uani 1 1 d . . . . .
H14A H 0.416873 0.709584 0.239390 0.053 Uiso 1 1 calc R U . . .
H14B H 0.440173 0.841683 0.214809 0.053 Uiso 1 1 calc R U . . .
C15 C 0.5136(3) 0.7252(3) 0.1372(2) 0.0592(9) Uani 1 1 d . . . . .
H15 H 0.603152 0.716805 0.156674 0.071 Uiso 1 1 calc R U . . .
C16 C 0.4883(4) 0.7019(3) 0.0634(3) 0.0742(11) Uani 1 1 d . . . . .
H16A H 0.400219 0.708991 0.041223 0.089 Uiso 1 1 calc R U . . .
H16B H 0.558024 0.677888 0.031795 0.089 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Fe1 2.3698(7) . ?
Br2 Fe1 2.3820(6) . ?
Fe1 N2 2.072(2) . ?
Fe1 N1 2.142(2) . ?
N1 C2 1.348(3) . ?
N1 C6 1.354(3) . ?
N2 C7 1.345(3) . ?
N2 N3 1.357(3) . ?
N3 C9 1.364(3) . ?
N3 C14 1.466(3) . ?
C1 C2 1.493(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 C3 1.393(4) . ?
C3 C4 1.367(4) . ?
C3 H3 0.9400 . ?
C4 C5 1.387(4) . ?
C4 H4 0.9400 . ?
C5 C6 1.388(3) . ?
C5 H5 0.9400 . ?
C6 C7 1.471(3) . ?
C7 C8 1.393(3) . ?
C8 C9 1.394(3) . ?
C8 H8 0.9400 . ?
C9 C10 1.512(3) . ?
C10 C12 1.534(4) . ?
C10 C13 1.535(4) . ?
C10 C11 1.537(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
C14 C15 1.490(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C15 C16 1.288(5) . ?
C15 H15 0.9400 . ?
C16 H16A 0.9400 . ?
C16 H16B 0.9400 . ?

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
N2 Fe1 N1 77.47(7) . . ?
N2 Fe1 Br1 111.67(6) . . ?
N1 Fe1 Br1 114.50(6) . . ?
N2 Fe1 Br2 115.79(6) . . ?
N1 Fe1 Br2 109.91(6) . . ?
Br1 Fe1 Br2 119.969(19) . . ?
C2 N1 C6 119.9(2) . . ?
C2 N1 Fe1 125.19(16) . . ?
C6 N1 Fe1 114.77(15) . . ?
C7 N2 N3 106.09(18) . . ?
C7 N2 Fe1 116.44(15) . . ?
N3 N2 Fe1 136.94(15) . . ?
N2 N3 C9 111.62(18) . . ?
N2 N3 C14 116.49(19) . . ?
C9 N3 C14 131.4(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 120.2(2) . . ?
N1 C2 C1 117.6(2) . . ?
C3 C2 C1 122.1(2) . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 118.1(2) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
N1 C6 C5 121.7(2) . . ?
N1 C6 C7 114.6(2) . . ?
C5 C6 C7 123.7(2) . . ?
N2 C7 C8 110.0(2) . . ?
N2 C7 C6 116.5(2) . . ?
C8 C7 C6 133.4(2) . . ?
C7 C8 C9 106.5(2) . . ?
C7 C8 H8 126.8 . . ?
C9 C8 H8 126.8 . . ?
N3 C9 C8 105.8(2) . . ?
N3 C9 C10 125.1(2) . . ?
C8 C9 C10 129.0(2) . . ?
C9 C10 C12 110.0(2) . . ?
C9 C10 C13 112.4(2) . . ?
C12 C10 C13 111.2(2) . . ?
C9 C10 C11 108.1(2) . . ?
C12 C10 C11 108.0(2) . . ?
C13 C10 C11 106.9(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C15 112.8(2) . . ?
N3 C14 H14A 109.0 . . ?
C15 C14 H14A 109.0 . . ?
N3 C14 H14B 109.0 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C16 C15 C14 126.2(3) . . ?
C16 C15 H15 116.9 . . ?
C14 C15 H15 116.9 . . ?
C15 C16 H16A 120.0 . . ?
C15 C16 H16B 120.0 . . ?
H16A C16 H16B 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N2 N3 C9 -0.9(3) . . . . ?
Fe1 N2 N3 C9 -171.70(18) . . . . ?
C7 N2 N3 C14 -173.9(2) . . . . ?
Fe1 N2 N3 C14 15.3(3) . . . . ?
C6 N1 C2 C3 1.2(4) . . . . ?
Fe1 N1 C2 C3 -174.35(19) . . . . ?
C6 N1 C2 C1 -176.6(2) . . . . ?
Fe1 N1 C2 C1 7.8(3) . . . . ?
N1 C2 C3 C4 0.0(4) . . . . ?
C1 C2 C3 C4 177.8(3) . . . . ?
C2 C3 C4 C5 -1.2(5) . . . . ?
C3 C4 C5 C6 1.1(5) . . . . ?
C2 N1 C6 C5 -1.3(4) . . . . ?
Fe1 N1 C6 C5 174.7(2) . . . . ?
C2 N1 C6 C7 178.8(2) . . . . ?
Fe1 N1 C6 C7 -5.2(3) . . . . ?
C4 C5 C6 N1 0.2(4) . . . . ?
C4 C5 C6 C7 -180.0(3) . . . . ?
N3 N2 C7 C8 1.0(3) . . . . ?
Fe1 N2 C7 C8 174.01(16) . . . . ?
N3 N2 C7 C6 -176.5(2) . . . . ?
Fe1 N2 C7 C6 -3.5(3) . . . . ?
N1 C6 C7 N2 5.8(3) . . . . ?
C5 C6 C7 N2 -174.1(2) . . . . ?
N1 C6 C7 C8 -171.0(3) . . . . ?
C5 C6 C7 C8 9.2(4) . . . . ?
N2 C7 C8 C9 -0.8(3) . . . . ?
C6 C7 C8 C9 176.1(3) . . . . ?
N2 N3 C9 C8 0.4(3) . . . . ?
C14 N3 C9 C8 172.0(2) . . . . ?
N2 N3 C9 C10 176.7(2) . . . . ?
C14 N3 C9 C10 -11.7(4) . . . . ?
C7 C8 C9 N3 0.2(3) . . . . ?
C7 C8 C9 C10 -175.9(2) . . . . ?
N3 C9 C10 C12 -64.5(3) . . . . ?
C8 C9 C10 C12 110.9(3) . . . . ?
N3 C9 C10 C13 60.0(3) . . . . ?
C8 C9 C10 C13 -124.6(3) . . . . ?
N3 C9 C10 C11 177.7(2) . . . . ?
C8 C9 C10 C11 -6.9(4) . . . . ?
N2 N3 C14 C15 81.4(3) . . . . ?
C9 N3 C14 C15 -89.9(3) . . . . ?
N3 C14 C15 C16 2.5(5) . . . . ?

_refine_diff_density_max         0.719
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.070


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_JK519_0m
_database_code_depnum_ccdc_archive 'CCDC 1941367'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller '
;Purdue University
United States of America
;
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H48 B Fe N5'
_chemical_formula_weight         617.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

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

_cell_length_a                   13.7625(7)
_cell_length_b                   16.9042(8)
_cell_length_c                   13.8498(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3222.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9467
_cell_measurement_theta_min      2.4095
_cell_measurement_theta_max      33.2104

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_F_000             1320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.430
_exptl_crystal_size_min          0.390
_exptl_absorpt_coefficient_mu    0.501
_shelx_estimated_absorpt_T_min   0.802
_shelx_estimated_absorpt_T_max   0.828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7166
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            211438
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.409
_diffrn_reflns_theta_max         33.279
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             12380
_reflns_number_gt                11177
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.931
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       'Apex3 v2018.1-0 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev937 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0445P)²+0.5193P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 5032 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.008(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         12380
_refine_ls_number_parameters     392
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0805
_refine_ls_wR_factor_gt          0.0766
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.20136(14) 0.35225(11) 0.23053(15) 0.0284(3) Uani 1 1 d . . . . .
H1A H 0.196668 0.320059 0.171862 0.043 Uiso 1 1 calc R U . . .
H1B H 0.138366 0.352784 0.263513 0.043 Uiso 1 1 calc R U . . .
H1C H 0.250691 0.329707 0.273505 0.043 Uiso 1 1 calc R U . . .
C2 C 0.22938(12) 0.43497(10) 0.20413(12) 0.0226(3) Uani 1 1 d . . . . .
C3 C 0.16092(13) 0.49524(12) 0.19490(14) 0.0303(4) Uani 1 1 d . . . . .
H3 H 0.093909 0.484642 0.205067 0.036 Uiso 1 1 calc R U . . .
C4 C 0.19150(13) 0.57060(11) 0.17079(17) 0.0318(4) Uani 1 1 d . . . . .
H4 H 0.145557 0.612256 0.164785 0.038 Uiso 1 1 calc R U . . .
C5 C 0.28941(14) 0.58519(10) 0.15541(13) 0.0270(3) Uani 1 1 d . . . . .
H5 H 0.311749 0.636790 0.139732 0.032 Uiso 1 1 calc R U . . .
C6 C 0.35393(11) 0.52249(9) 0.16351(11) 0.0202(3) Uani 1 1 d . . . . .
C7 C 0.45800(12) 0.52983(9) 0.14267(12) 0.0198(3) Uani 1 1 d . . . . .
C8 C 0.51765(13) 0.59440(10) 0.12204(13) 0.0243(3) Uani 1 1 d . . . . .
H8 H 0.499162 0.648510 0.119635 0.029 Uiso 1 1 calc R U . . .
C9 C 0.60939(12) 0.56338(9) 0.10579(12) 0.0216(3) Uani 1 1 d . . . . .
C10 C 0.70206(13) 0.60632(11) 0.07779(14) 0.0263(3) Uani 1 1 d . . . . .
C11 C 0.6870(2) 0.69468(13) 0.0962(3) 0.0531(7) Uani 1 1 d . . . . .
H11A H 0.745642 0.723732 0.077491 0.080 Uiso 1 1 calc R U . . .
H11B H 0.673944 0.703353 0.164995 0.080 Uiso 1 1 calc R U . . .
H11C H 0.631696 0.713567 0.058066 0.080 Uiso 1 1 calc R U . . .
C12 C 0.72348(16) 0.59361(15) -0.02951(15) 0.0365(5) Uani 1 1 d . . . . .
H12A H 0.668140 0.612024 -0.067950 0.055 Uiso 1 1 calc R U . . .
H12B H 0.734291 0.537192 -0.041711 0.055 Uiso 1 1 calc R U . . .
H12C H 0.781731 0.623492 -0.047579 0.055 Uiso 1 1 calc R U . . .
C13 C 0.79017(16) 0.57946(14) 0.13851(16) 0.0377(5) Uani 1 1 d . . . . .
H13A H 0.814703 0.529057 0.113452 0.057 Uiso 1 1 calc R U . . .
H13B H 0.770232 0.572748 0.205947 0.057 Uiso 1 1 calc R U . . .
H13C H 0.841488 0.619525 0.134684 0.057 Uiso 1 1 calc R U . . .
C14 C 0.67665(12) 0.42169(10) 0.11387(14) 0.0244(3) Uani 1 1 d . . . . .
H14A H 0.707525 0.417119 0.178190 0.029 Uiso 1 1 calc R U . . .
H14B H 0.727469 0.437635 0.067177 0.029 Uiso 1 1 calc R U . . .
C15 C 0.63634(12) 0.34117(10) 0.08455(13) 0.0235(3) Uani 1 1 d . . . . .
H15A H 0.591225 0.322921 0.135579 0.028 Uiso 1 1 calc R U . . .
H15B H 0.690851 0.303024 0.081751 0.028 Uiso 1 1 calc R U . . .
C16 C 0.58247(14) 0.33914(10) -0.01278(13) 0.0243(3) Uani 1 1 d . . . . .
H16A H 0.630109 0.326719 -0.064147 0.029 Uiso 1 1 calc R U . . .
H16B H 0.556538 0.392681 -0.025990 0.029 Uiso 1 1 calc R U . . .
C17 C 0.51931(13) 0.18658(10) 0.01680(13) 0.0225(3) Uani 1 1 d . . . . .
H17 H 0.539083 0.189959 0.086158 0.027 Uiso 1 1 calc R U . . .
C18 C 0.43153(14) 0.13009(11) 0.00952(14) 0.0265(3) Uani 1 1 d . . . . .
H18A H 0.453744 0.075941 0.025490 0.032 Uiso 1 1 calc R U . . .
H18B H 0.383184 0.145720 0.058892 0.032 Uiso 1 1 calc R U . . .
C19 C 0.38070(17) 0.12776(12) -0.08927(15) 0.0328(4) Uani 1 1 d . . . . .
H19A H 0.420261 0.095473 -0.134113 0.039 Uiso 1 1 calc R U . . .
H19B H 0.316959 0.101300 -0.081831 0.039 Uiso 1 1 calc R U . . .
C20 C 0.36463(16) 0.20964(12) -0.13420(14) 0.0320(4) Uani 1 1 d . . . . .
H20A H 0.310953 0.236291 -0.099472 0.038 Uiso 1 1 calc R U . . .
H20B H 0.344127 0.202762 -0.202203 0.038 Uiso 1 1 calc R U . . .
C21 C 0.45450(16) 0.26335(11) -0.13166(13) 0.0288(4) Uani 1 1 d . . . . .
H21 H 0.435475 0.316312 -0.157686 0.035 Uiso 1 1 calc R U . . .
C22 C 0.53944(19) 0.23147(13) -0.19348(15) 0.0376(4) Uani 1 1 d . . . . .
H22A H 0.513491 0.216493 -0.257592 0.045 Uiso 1 1 calc R U . . .
H22B H 0.586413 0.275046 -0.203626 0.045 Uiso 1 1 calc R U . . .
C23 C 0.5951(2) 0.15975(14) -0.15180(17) 0.0416(5) Uani 1 1 d . . . . .
H23A H 0.560861 0.110967 -0.171977 0.050 Uiso 1 1 calc R U . . .
H23B H 0.660522 0.158521 -0.181458 0.050 Uiso 1 1 calc R U . . .
C24 C 0.60727(16) 0.15754(12) -0.04182(16) 0.0322(4) Uani 1 1 d . . . . .
H24A H 0.664233 0.190330 -0.024363 0.039 Uiso 1 1 calc R U . . .
H24B H 0.621822 0.102451 -0.022354 0.039 Uiso 1 1 calc R U . . .
C25 C 0.47109(11) 0.23761(9) 0.33314(12) 0.0200(3) Uani 1 1 d . . . . .
C26 C 0.43096(12) 0.18227(10) 0.26883(13) 0.0231(3) Uani 1 1 d . . . . .
H26 H 0.406915 0.200066 0.208313 0.028 Uiso 1 1 calc R U . . .
C27 C 0.42540(14) 0.10239(11) 0.29110(16) 0.0297(4) Uani 1 1 d . . . . .
H27 H 0.399153 0.066345 0.245390 0.036 Uiso 1 1 calc R U . . .
C28 C 0.45812(15) 0.07470(11) 0.38015(18) 0.0339(4) Uani 1 1 d . . . . .
H28 H 0.456004 0.019886 0.395167 0.041 Uiso 1 1 calc R U . . .
C29 C 0.49383(15) 0.12899(13) 0.44637(17) 0.0333(4) Uani 1 1 d . . . . .
H29 H 0.514348 0.111089 0.508115 0.040 Uiso 1 1 calc R U . . .
C30 C 0.50021(13) 0.20892(11) 0.42428(14) 0.0273(3) Uani 1 1 d . . . . .
H30 H 0.524536 0.244797 0.471213 0.033 Uiso 1 1 calc R U . . .
C31 C 0.54843(13) 0.36508(10) 0.34974(12) 0.0205(3) Uani 1 1 d . . . . .
C32 C 0.64202(13) 0.33827(11) 0.37430(14) 0.0262(3) Uani 1 1 d . . . . .
H32 H 0.657357 0.283723 0.367989 0.031 Uiso 1 1 calc R U . . .
C33 C 0.71198(14) 0.39037(13) 0.40751(15) 0.0319(4) Uani 1 1 d . . . . .
H33 H 0.774121 0.370819 0.425466 0.038 Uiso 1 1 calc R U . . .
C34 C 0.69280(15) 0.47078(13) 0.41503(16) 0.0346(4) Uani 1 1 d . . . . .
H34 H 0.741841 0.506496 0.435779 0.042 Uiso 1 1 calc R U . . .
C35 C 0.60056(16) 0.49798(11) 0.39164(14) 0.0310(4) Uani 1 1 d . . . . .
H35 H 0.586559 0.552871 0.396376 0.037 Uiso 1 1 calc R U . . .
C36 C 0.52843(13) 0.44608(10) 0.36140(13) 0.0236(3) Uani 1 1 d . . . . .
H36 H 0.464983 0.465518 0.348467 0.028 Uiso 1 1 calc R U . . .
B1 B 0.49244(14) 0.27546(11) -0.02020(13) 0.0216(3) Uani 1 1 d . . . . .
N1 N 0.32429(9) 0.44863(7) 0.18722(11) 0.0188(2) Uani 1 1 d . . . . .
N2 N 0.50977(10) 0.46273(8) 0.14068(10) 0.0194(2) Uani 1 1 d . . . . .
N3 N 0.60152(10) 0.48348(8) 0.11756(10) 0.0196(2) Uani 1 1 d . . . . .
N4 N 0.40526(11) 0.31083(8) 0.04689(11) 0.0217(3) Uani 1 1 d . . . . .
H4A H 0.362132 0.270898 0.057129 0.026 Uiso 1 1 calc R U . . .
H4B H 0.373873 0.348260 0.011434 0.026 Uiso 1 1 calc R U . . .
N5 N 0.47801(10) 0.31649(8) 0.30535(11) 0.0204(2) Uani 1 1 d . . . . .
Fe1 Fe 0.43607(2) 0.36008(2) 0.17891(2) 0.01709(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.496(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 N1 1.347(2) . ?
C2 C3 1.393(2) . ?
C3 C4 1.383(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(2) . ?
C5 H5 0.9500 . ?
C6 N1 1.3538(19) . ?
C6 C7 1.466(2) . ?
C7 N2 1.340(2) . ?
C7 C8 1.395(2) . ?
C8 C9 1.385(2) . ?
C8 H8 0.9500 . ?
C9 N3 1.365(2) . ?
C9 C10 1.518(2) . ?
C10 C11 1.530(3) . ?
C10 C12 1.530(3) . ?
C10 C13 1.544(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 N3 1.470(2) . ?
C14 C15 1.525(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.539(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 B1 1.644(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C24 1.538(3) . ?
C17 C18 1.543(2) . ?
C17 B1 1.630(3) . ?
C17 H17 1.0000 . ?
C18 C19 1.537(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.534(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.535(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.546(3) . ?
C21 B1 1.643(3) . ?
C21 H21 1.0000 . ?
C22 C23 1.546(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.533(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 N5 1.391(2) . ?
C25 C26 1.405(2) . ?
C25 C30 1.410(2) . ?
C26 C27 1.387(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.394(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.387(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.388(3) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C36 1.406(2) . ?
C31 C32 1.407(2) . ?
C31 N5 1.411(2) . ?
C32 C33 1.384(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.389(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.389(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.389(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
B1 N4 1.631(2) . ?
N1 Fe1 2.1496(12) . ?
N2 N3 1.3491(19) . ?
N2 Fe1 2.0786(14) . ?
N4 Fe1 2.0533(14) . ?
N4 H4A 0.9100 . ?
N4 H4B 0.9100 . ?
N5 Fe1 1.9856(15) . ?

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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 120.95(16) . . ?
N1 C2 C1 116.92(15) . . ?
C3 C2 C1 122.11(16) . . ?
C4 C3 C2 119.34(16) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 119.79(16) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 118.28(17) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
N1 C6 C5 122.10(15) . . ?
N1 C6 C7 114.84(13) . . ?
C5 C6 C7 123.00(15) . . ?
N2 C7 C8 110.19(15) . . ?
N2 C7 C6 116.87(14) . . ?
C8 C7 C6 132.94(15) . . ?
C9 C8 C7 105.86(14) . . ?
C9 C8 H8 127.1 . . ?
C7 C8 H8 127.1 . . ?
N3 C9 C8 106.43(14) . . ?
N3 C9 C10 124.78(15) . . ?
C8 C9 C10 128.77(15) . . ?
C9 C10 C11 108.07(16) . . ?
C9 C10 C12 110.06(15) . . ?
C11 C10 C12 109.0(2) . . ?
C9 C10 C13 112.34(15) . . ?
C11 C10 C13 107.62(18) . . ?
C12 C10 C13 109.66(17) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C15 112.80(13) . . ?
N3 C14 H14A 109.0 . . ?
C15 C14 H14A 109.0 . . ?
N3 C14 H14B 109.0 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 C16 115.37(14) . . ?
C14 C15 H15A 108.4 . . ?
C16 C15 H15A 108.4 . . ?
C14 C15 H15B 108.4 . . ?
C16 C15 H15B 108.4 . . ?
H15A C15 H15B 107.5 . . ?
C15 C16 B1 115.62(14) . . ?
C15 C16 H16A 108.4 . . ?
B1 C16 H16A 108.4 . . ?
C15 C16 H16B 108.4 . . ?
B1 C16 H16B 108.4 . . ?
H16A C16 H16B 107.4 . . ?
C24 C17 C18 112.59(15) . . ?
C24 C17 B1 107.87(14) . . ?
C18 C17 B1 111.86(15) . . ?
C24 C17 H17 108.1 . . ?
C18 C17 H17 108.1 . . ?
B1 C17 H17 108.1 . . ?
C19 C18 C17 115.48(16) . . ?
C19 C18 H18A 108.4 . . ?
C17 C18 H18A 108.4 . . ?
C19 C18 H18B 108.4 . . ?
C17 C18 H18B 108.4 . . ?
H18A C18 H18B 107.5 . . ?
C20 C19 C18 113.81(15) . . ?
C20 C19 H19A 108.8 . . ?
C18 C19 H19A 108.8 . . ?
C20 C19 H19B 108.8 . . ?
C18 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C19 C20 C21 114.11(17) . . ?
C19 C20 H20A 108.7 . . ?
C21 C20 H20A 108.7 . . ?
C19 C20 H20B 108.7 . . ?
C21 C20 H20B 108.7 . . ?
H20A C20 H20B 107.6 . . ?
C20 C21 C22 112.99(16) . . ?
C20 C21 B1 110.58(15) . . ?
C22 C21 B1 108.88(17) . . ?
C20 C21 H21 108.1 . . ?
C22 C21 H21 108.1 . . ?
B1 C21 H21 108.1 . . ?
C23 C22 C21 116.18(17) . . ?
C23 C22 H22A 108.2 . . ?
C21 C22 H22A 108.2 . . ?
C23 C22 H22B 108.2 . . ?
C21 C22 H22B 108.2 . . ?
H22A C22 H22B 107.4 . . ?
C24 C23 C22 116.38(17) . . ?
C24 C23 H23A 108.2 . . ?
C22 C23 H23A 108.2 . . ?
C24 C23 H23B 108.2 . . ?
C22 C23 H23B 108.2 . . ?
H23A C23 H23B 107.3 . . ?
C23 C24 C17 115.51(18) . . ?
C23 C24 H24A 108.4 . . ?
C17 C24 H24A 108.4 . . ?
C23 C24 H24B 108.4 . . ?
C17 C24 H24B 108.4 . . ?
H24A C24 H24B 107.5 . . ?
N5 C25 C26 119.33(15) . . ?
N5 C25 C30 123.91(15) . . ?
C26 C25 C30 116.75(15) . . ?
C27 C26 C25 121.93(17) . . ?
C27 C26 H26 119.0 . . ?
C25 C26 H26 119.0 . . ?
C26 C27 C28 120.39(19) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C29 C28 C27 118.50(17) . . ?
C29 C28 H28 120.8 . . ?
C27 C28 H28 120.8 . . ?
C28 C29 C30 121.37(19) . . ?
C28 C29 H29 119.3 . . ?
C30 C29 H29 119.3 . . ?
C29 C30 C25 120.94(18) . . ?
C29 C30 H30 119.5 . . ?
C25 C30 H30 119.5 . . ?
C36 C31 C32 117.72(16) . . ?
C36 C31 N5 118.84(16) . . ?
C32 C31 N5 123.12(15) . . ?
C33 C32 C31 120.82(18) . . ?
C33 C32 H32 119.6 . . ?
C31 C32 H32 119.6 . . ?
C32 C33 C34 121.05(19) . . ?
C32 C33 H33 119.5 . . ?
C34 C33 H33 119.5 . . ?
C35 C34 C33 118.71(17) . . ?
C35 C34 H34 120.6 . . ?
C33 C34 H34 120.6 . . ?
C34 C35 C36 120.97(18) . . ?
C34 C35 H35 119.5 . . ?
C36 C35 H35 119.5 . . ?
C35 C36 C31 120.64(17) . . ?
C35 C36 H36 119.7 . . ?
C31 C36 H36 119.7 . . ?
C17 B1 N4 109.01(13) . . ?
C17 B1 C21 104.64(14) . . ?
N4 B1 C21 110.32(14) . . ?
C17 B1 C16 114.38(15) . . ?
N4 B1 C16 106.18(13) . . ?
C21 B1 C16 112.33(14) . . ?
C2 N1 C6 119.50(13) . . ?
C2 N1 Fe1 125.73(11) . . ?
C6 N1 Fe1 114.43(10) . . ?
C7 N2 N3 106.42(13) . . ?
C7 N2 Fe1 116.23(11) . . ?
N3 N2 Fe1 137.24(11) . . ?
N2 N3 C9 111.09(14) . . ?
N2 N3 C14 118.80(13) . . ?
C9 N3 C14 130.02(14) . . ?
B1 N4 Fe1 120.26(11) . . ?
B1 N4 H4A 107.3 . . ?
Fe1 N4 H4A 107.3 . . ?
B1 N4 H4B 107.3 . . ?
Fe1 N4 H4B 107.3 . . ?
H4A N4 H4B 106.9 . . ?
C25 N5 C31 118.97(14) . . ?
C25 N5 Fe1 125.44(11) . . ?
C31 N5 Fe1 111.58(11) . . ?
N5 Fe1 N4 134.02(6) . . ?
N5 Fe1 N2 113.12(6) . . ?
N4 Fe1 N2 102.26(6) . . ?
N5 Fe1 N1 114.79(6) . . ?
N4 Fe1 N1 100.50(6) . . ?
N2 Fe1 N1 77.38(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 -1.9(3) . . . . ?
C1 C2 C3 C4 179.67(18) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C4 C5 C6 N1 -1.0(3) . . . . ?
C4 C5 C6 C7 175.88(17) . . . . ?
N1 C6 C7 N2 5.9(2) . . . . ?
C5 C6 C7 N2 -171.26(15) . . . . ?
N1 C6 C7 C8 -175.30(18) . . . . ?
C5 C6 C7 C8 7.6(3) . . . . ?
N2 C7 C8 C9 0.8(2) . . . . ?
C6 C7 C8 C9 -178.10(17) . . . . ?
C7 C8 C9 N3 -0.34(19) . . . . ?
C7 C8 C9 C10 178.19(17) . . . . ?
N3 C9 C10 C11 -166.4(2) . . . . ?
C8 C9 C10 C11 15.4(3) . . . . ?
N3 C9 C10 C12 74.7(2) . . . . ?
C8 C9 C10 C12 -103.6(2) . . . . ?
N3 C9 C10 C13 -47.8(2) . . . . ?
C8 C9 C10 C13 133.9(2) . . . . ?
N3 C14 C15 C16 56.6(2) . . . . ?
C14 C15 C16 B1 -147.84(15) . . . . ?
C24 C17 C18 C19 -70.0(2) . . . . ?
B1 C17 C18 C19 51.7(2) . . . . ?
C17 C18 C19 C20 -44.1(2) . . . . ?
C18 C19 C20 C21 47.2(2) . . . . ?
C19 C20 C21 C22 64.8(2) . . . . ?
C19 C20 C21 B1 -57.6(2) . . . . ?
C20 C21 C22 C23 -73.9(3) . . . . ?
B1 C21 C22 C23 49.3(2) . . . . ?
C21 C22 C23 C24 -35.4(3) . . . . ?
C22 C23 C24 C17 38.3(3) . . . . ?
C18 C17 C24 C23 68.8(2) . . . . ?
B1 C17 C24 C23 -55.1(2) . . . . ?
N5 C25 C26 C27 177.61(16) . . . . ?
C30 C25 C26 C27 -3.8(2) . . . . ?
C25 C26 C27 C28 1.4(3) . . . . ?
C26 C27 C28 C29 1.6(3) . . . . ?
C27 C28 C29 C30 -2.1(3) . . . . ?
C28 C29 C30 C25 -0.4(3) . . . . ?
N5 C25 C30 C29 -178.17(17) . . . . ?
C26 C25 C30 C29 3.3(3) . . . . ?
C36 C31 C32 C33 -0.8(3) . . . . ?
N5 C31 C32 C33 172.57(18) . . . . ?
C31 C32 C33 C34 -1.8(3) . . . . ?
C32 C33 C34 C35 2.2(3) . . . . ?
C33 C34 C35 C36 0.1(3) . . . . ?
C34 C35 C36 C31 -2.8(3) . . . . ?
C32 C31 C36 C35 3.1(3) . . . . ?
N5 C31 C36 C35 -170.60(17) . . . . ?
C24 C17 B1 N4 -175.22(15) . . . . ?
C18 C17 B1 N4 60.43(18) . . . . ?
C24 C17 B1 C21 66.77(18) . . . . ?
C18 C17 B1 C21 -57.57(18) . . . . ?
C24 C17 B1 C16 -56.56(19) . . . . ?
C18 C17 B1 C16 179.10(14) . . . . ?
C20 C21 B1 C17 60.64(18) . . . . ?
C22 C21 B1 C17 -64.06(18) . . . . ?
C20 C21 B1 N4 -56.47(19) . . . . ?
C22 C21 B1 N4 178.83(14) . . . . ?
C20 C21 B1 C16 -174.72(15) . . . . ?
C22 C21 B1 C16 60.58(19) . . . . ?
C15 C16 B1 C17 -48.7(2) . . . . ?
C15 C16 B1 N4 71.60(18) . . . . ?
C15 C16 B1 C21 -167.73(14) . . . . ?
C3 C2 N1 C6 1.8(2) . . . . ?
C1 C2 N1 C6 -179.67(15) . . . . ?
C3 C2 N1 Fe1 -171.06(13) . . . . ?
C1 C2 N1 Fe1 7.4(2) . . . . ?
C5 C6 N1 C2 -0.3(2) . . . . ?
C7 C6 N1 C2 -177.50(15) . . . . ?
C5 C6 N1 Fe1 173.32(13) . . . . ?
C7 C6 N1 Fe1 -3.83(17) . . . . ?
C8 C7 N2 N3 -0.93(19) . . . . ?
C6 C7 N2 N3 178.17(13) . . . . ?
C8 C7 N2 Fe1 175.94(12) . . . . ?
C6 C7 N2 Fe1 -4.97(19) . . . . ?
C7 N2 N3 C9 0.71(18) . . . . ?
Fe1 N2 N3 C9 -175.14(13) . . . . ?
C7 N2 N3 C14 177.49(14) . . . . ?
Fe1 N2 N3 C14 1.6(2) . . . . ?
C8 C9 N3 N2 -0.22(19) . . . . ?
C10 C9 N3 N2 -178.83(15) . . . . ?
C8 C9 N3 C14 -176.54(17) . . . . ?
C10 C9 N3 C14 4.9(3) . . . . ?
C15 C14 N3 N2 30.5(2) . . . . ?
C15 C14 N3 C9 -153.40(16) . . . . ?
C17 B1 N4 Fe1 81.75(15) . . . . ?
C21 B1 N4 Fe1 -163.89(11) . . . . ?
C16 B1 N4 Fe1 -41.93(16) . . . . ?
C26 C25 N5 C31 -155.94(15) . . . . ?
C30 C25 N5 C31 25.6(2) . . . . ?
C26 C25 N5 Fe1 -0.4(2) . . . . ?
C30 C25 N5 Fe1 -178.93(13) . . . . ?
C36 C31 N5 C25 -148.68(16) . . . . ?
C32 C31 N5 C25 38.0(2) . . . . ?
C36 C31 N5 Fe1 52.62(18) . . . . ?
C32 C31 N5 Fe1 -120.72(16) . . . . ?

_refine_diff_density_max         0.602
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.047


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_jk4180_0m_sq
_database_code_depnum_ccdc_archive 'CCDC 1941369'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller '
;Purdue University
United States of America
;
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H36 B Br2 Fe N3'
_chemical_formula_weight         593.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   15.581(3)
_cell_length_b                   11.673(2)
_cell_length_c                   16.580(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.635(6)
_cell_angle_gamma                90
_cell_volume                     3015.4(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9017
_cell_measurement_theta_min      2.1834
_cell_measurement_theta_max      28.2265

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_F_000             1208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.470
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    3.164
_shelx_estimated_absorpt_T_min   0.253
_shelx_estimated_absorpt_T_max   0.858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1009
_exptl_absorpt_correction_T_max  0.2627
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS APEXII Kappa CCD diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24458
_diffrn_reflns_av_unetI/netI     0.1125
_diffrn_reflns_av_R_equivalents  0.0840
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.134
_diffrn_reflns_theta_max         28.285
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7459
_reflns_number_gt                5160
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 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.
;

_computing_data_collection       'Apex3 v2017.3-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev924 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
; 
The structure contains two solvent accessible voids of 548 Ang3 
combined. The content of the voids was ill defined. Attempts at 
refinement as disordered pentane required strong restraints and were 
altogether unsatisfactory. The structure factors were instead augmented 
via reverse Fourier transform methods using the SQUEEZE routine (P. 
van der Sluis & A.L. Spek (1990). Acta Cryst. A46, 194-201) as 
implemented in the program Platon. The resultant FAB file containing the 
structure factor contribution from the electron content of the void 
space was used in together with the original hkl file in the further 
refinement. (The FAB file with details of the Squeeze results is 
appended to this cif file). The Squeeze procedure corrected for 130
electrons within the solvent accessible voids.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0761P)²+0.1199P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7459
_refine_ls_number_parameters     285
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0587
_refine_ls_wR_factor_ref         0.1744
_refine_ls_wR_factor_gt          0.1548
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.0387(3) 0.5391(4) 0.6319(2) 0.0346(10) Uani 1 1 d . . . . .
H1A H -0.008415 0.503673 0.601295 0.052 Uiso 1 1 calc R U . . .
H1B H 0.089907 0.542894 0.598128 0.052 Uiso 1 1 calc R U . . .
H1C H 0.022159 0.616744 0.648020 0.052 Uiso 1 1 calc R U . . .
C2 C 0.0580(3) 0.4689(3) 0.7057(2) 0.0244(8) Uani 1 1 d . . . . .
C3 C 0.0465(3) 0.5106(3) 0.7837(2) 0.0261(8) Uani 1 1 d . . . . .
H3 H 0.026777 0.586752 0.791552 0.031 Uiso 1 1 calc R U . . .
C4 C 0.0638(2) 0.4411(3) 0.8496(2) 0.0248(8) Uani 1 1 d . . . . .
H4 H 0.053862 0.468350 0.902661 0.030 Uiso 1 1 calc R U . . .
C5 C 0.0957(3) 0.3317(3) 0.8377(2) 0.0265(8) Uani 1 1 d . . . . .
H5 H 0.109041 0.283204 0.882120 0.032 Uiso 1 1 calc R U . . .
C6 C 0.1074(2) 0.2952(3) 0.7590(2) 0.0217(7) Uani 1 1 d . . . . .
C7 C 0.1407(2) 0.1801(3) 0.7391(2) 0.0223(8) Uani 1 1 d . . . . .
C8 C 0.1671(2) 0.0882(3) 0.7868(2) 0.0249(8) Uani 1 1 d . . . . .
H8 H 0.171110 0.085927 0.844023 0.030 Uiso 1 1 calc R U . . .
C9 C 0.1861(2) 0.0005(3) 0.7334(2) 0.0237(8) Uani 1 1 d . . . . .
C10 C 0.2162(3) -0.1200(3) 0.7536(3) 0.0287(9) Uani 1 1 d . . . . .
C11 C 0.2308(3) -0.1273(4) 0.8448(3) 0.0407(11) Uani 1 1 d . . . . .
H11A H 0.275165 -0.072229 0.861178 0.061 Uiso 1 1 calc R U . . .
H11B H 0.249413 -0.204923 0.859239 0.061 Uiso 1 1 calc R U . . .
H11C H 0.177197 -0.109495 0.872528 0.061 Uiso 1 1 calc R U . . .
C12 C 0.1481(3) -0.2088(3) 0.7301(3) 0.0399(11) Uani 1 1 d . . . . .
H12A H 0.138030 -0.206108 0.671694 0.060 Uiso 1 1 calc R U . . .
H12B H 0.094550 -0.191665 0.758096 0.060 Uiso 1 1 calc R U . . .
H12C H 0.168190 -0.285338 0.745504 0.060 Uiso 1 1 calc R U . . .
C13 C 0.3022(3) -0.1449(4) 0.7124(3) 0.0423(12) Uani 1 1 d . . . . .
H13A H 0.343524 -0.084588 0.726331 0.063 Uiso 1 1 calc R U . . .
H13B H 0.293468 -0.146780 0.653792 0.063 Uiso 1 1 calc R U . . .
H13C H 0.324258 -0.219082 0.730846 0.063 Uiso 1 1 calc R U . . .
C14 C 0.1801(3) -0.0093(3) 0.5773(2) 0.0252(8) Uani 1 1 d . . . . .
H14A H 0.127946 0.008374 0.544934 0.030 Uiso 1 1 calc R U . . .
H14B H 0.183738 -0.093605 0.582951 0.030 Uiso 1 1 calc R U . . .
C15 C 0.2584(3) 0.0331(4) 0.5323(2) 0.0286(9) Uani 1 1 d . . . . .
H15A H 0.310221 0.022367 0.566521 0.034 Uiso 1 1 calc R U . . .
H15B H 0.252107 0.116000 0.521144 0.034 Uiso 1 1 calc R U . . .
C16 C 0.2698(3) -0.0315(4) 0.4524(2) 0.0299(9) Uani 1 1 d . . . . .
H16A H 0.214271 -0.028688 0.422840 0.036 Uiso 1 1 calc R U . . .
H16B H 0.281066 -0.112842 0.465606 0.036 Uiso 1 1 calc R U . . .
C17 C 0.4059(3) 0.1103(4) 0.4066(3) 0.0432(12) Uani 1 1 d . . . . .
H17 H 0.403206 0.138193 0.463570 0.052 Uiso 1 1 calc R U . . .
C18 C 0.3693(4) 0.2029(5) 0.3478(4) 0.0686(19) Uani 1 1 d . . . . .
H18A H 0.311315 0.225089 0.365817 0.082 Uiso 1 1 calc R U . . .
H18B H 0.406237 0.271875 0.351076 0.082 Uiso 1 1 calc R U . . .
C19 C 0.3635(4) 0.1643(5) 0.2595(4) 0.0655(17) Uani 1 1 d . . . . .
H19A H 0.422164 0.156057 0.237948 0.079 Uiso 1 1 calc R U . . .
H19B H 0.333556 0.224060 0.227468 0.079 Uiso 1 1 calc R U . . .
C20 C 0.3154(4) 0.0499(6) 0.2495(3) 0.0624(17) Uani 1 1 d . . . . .
H20A H 0.253702 0.062490 0.260328 0.075 Uiso 1 1 calc R U . . .
H20B H 0.320443 0.023815 0.192977 0.075 Uiso 1 1 calc R U . . .
C21 C 0.3491(3) -0.0441(4) 0.3056(3) 0.0399(11) Uani 1 1 d . . . . .
H21 H 0.311599 -0.113311 0.300946 0.048 Uiso 1 1 calc R U . . .
C22 C 0.4441(3) -0.0779(5) 0.2885(3) 0.0497(13) Uani 1 1 d . . . . .
H22A H 0.447216 -0.161782 0.280244 0.060 Uiso 1 1 calc R U . . .
H22B H 0.462312 -0.040468 0.237936 0.060 Uiso 1 1 calc R U . . .
C23 C 0.5061(3) -0.0446(6) 0.3558(4) 0.0652(17) Uani 1 1 d . . . . .
H23A H 0.497740 -0.097632 0.401625 0.078 Uiso 1 1 calc R U . . .
H23B H 0.565399 -0.055749 0.336322 0.078 Uiso 1 1 calc R U . . .
C24 C 0.4981(3) 0.0753(5) 0.3861(3) 0.0544(14) Uani 1 1 d . . . . .
H24A H 0.520195 0.128320 0.344630 0.065 Uiso 1 1 calc R U . . .
H24B H 0.534547 0.083933 0.434965 0.065 Uiso 1 1 calc R U . . .
B1 B 0.3413(3) 0.0090(4) 0.3931(3) 0.0335(11) Uani 1 1 d . . . . .
N1 N 0.0876(2) 0.3612(2) 0.69426(17) 0.0204(6) Uani 1 1 d . . . . .
N2 N 0.1434(2) 0.1525(3) 0.65973(18) 0.0215(7) Uani 1 1 d . . . . .
N3 N 0.1716(2) 0.0420(3) 0.65766(18) 0.0226(7) Uani 1 1 d . . . . .
Fe1 Fe 0.10328(4) 0.27938(4) 0.58088(3) 0.02310(16) Uani 1 1 d . . . . .
Br1 Br -0.03260(3) 0.22247(4) 0.52569(2) 0.03245(14) Uani 1 1 d . . . . .
Br2 Br 0.21432(3) 0.37088(4) 0.50823(2) 0.03699(15) 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 1.501(6) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 N1 1.353(5) . ?
C2 C3 1.395(5) . ?
C3 C4 1.385(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(5) . ?
C5 H5 0.9500 . ?
C6 N1 1.354(5) . ?
C6 C7 1.478(5) . ?
C7 N2 1.356(4) . ?
C7 C8 1.393(5) . ?
C8 C9 1.388(5) . ?
C8 H8 0.9500 . ?
C9 N3 1.363(5) . ?
C9 C10 1.518(5) . ?
C10 C11 1.530(6) . ?
C10 C12 1.531(6) . ?
C10 C13 1.538(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 N3 1.469(4) . ?
C14 C15 1.520(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.535(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 B1 1.567(6) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C24 1.534(6) . ?
C17 C18 1.560(8) . ?
C17 B1 1.568(7) . ?
C17 H17 1.0000 . ?
C18 C19 1.533(9) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.539(9) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.528(8) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.561(6) . ?
C21 B1 1.583(6) . ?
C21 H21 1.0000 . ?
C22 C23 1.518(8) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.493(8) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
N1 Fe1 2.125(3) . ?
N2 N3 1.363(4) . ?
N2 Fe1 2.068(3) . ?
Fe1 Br2 2.3730(7) . ?
Fe1 Br1 2.3913(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 120.1(4) . . ?
N1 C2 C1 117.3(3) . . ?
C3 C2 C1 122.6(4) . . ?
C4 C3 C2 120.1(4) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 117.9(4) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
N1 C6 C5 122.6(3) . . ?
N1 C6 C7 114.7(3) . . ?
C5 C6 C7 122.7(3) . . ?
N2 C7 C8 110.9(3) . . ?
N2 C7 C6 116.6(3) . . ?
C8 C7 C6 132.5(3) . . ?
C9 C8 C7 105.6(3) . . ?
C9 C8 H8 127.2 . . ?
C7 C8 H8 127.2 . . ?
N3 C9 C8 106.9(3) . . ?
N3 C9 C10 125.5(3) . . ?
C8 C9 C10 127.6(3) . . ?
C9 C10 C11 108.2(3) . . ?
C9 C10 C12 111.1(4) . . ?
C11 C10 C12 108.0(3) . . ?
C9 C10 C13 110.2(3) . . ?
C11 C10 C13 107.9(4) . . ?
C12 C10 C13 111.3(4) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C15 113.2(3) . . ?
N3 C14 H14A 108.9 . . ?
C15 C14 H14A 108.9 . . ?
N3 C14 H14B 108.9 . . ?
C15 C14 H14B 108.9 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 C16 111.4(3) . . ?
C14 C15 H15A 109.4 . . ?
C16 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
C16 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C15 C16 B1 118.9(4) . . ?
C15 C16 H16A 107.6 . . ?
B1 C16 H16A 107.6 . . ?
C15 C16 H16B 107.6 . . ?
B1 C16 H16B 107.6 . . ?
H16A C16 H16B 107.0 . . ?
C24 C17 C18 112.5(4) . . ?
C24 C17 B1 111.6(4) . . ?
C18 C17 B1 101.7(4) . . ?
C24 C17 H17 110.3 . . ?
C18 C17 H17 110.3 . . ?
B1 C17 H17 110.3 . . ?
C19 C18 C17 114.3(5) . . ?
C19 C18 H18A 108.7 . . ?
C17 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C17 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C18 C19 C20 112.4(5) . . ?
C18 C19 H19A 109.1 . . ?
C20 C19 H19A 109.1 . . ?
C18 C19 H19B 109.1 . . ?
C20 C19 H19B 109.1 . . ?
H19A C19 H19B 107.9 . . ?
C21 C20 C19 113.2(5) . . ?
C21 C20 H20A 108.9 . . ?
C19 C20 H20A 108.9 . . ?
C21 C20 H20B 108.9 . . ?
C19 C20 H20B 108.9 . . ?
H20A C20 H20B 107.8 . . ?
C20 C21 C22 113.1(4) . . ?
C20 C21 B1 104.3(4) . . ?
C22 C21 B1 110.4(4) . . ?
C20 C21 H21 109.6 . . ?
C22 C21 H21 109.6 . . ?
B1 C21 H21 109.6 . . ?
C23 C22 C21 113.5(4) . . ?
C23 C22 H22A 108.9 . . ?
C21 C22 H22A 108.9 . . ?
C23 C22 H22B 108.9 . . ?
C21 C22 H22B 108.9 . . ?
H22A C22 H22B 107.7 . . ?
C24 C23 C22 115.6(5) . . ?
C24 C23 H23A 108.4 . . ?
C22 C23 H23A 108.4 . . ?
C24 C23 H23B 108.4 . . ?
C22 C23 H23B 108.4 . . ?
H23A C23 H23B 107.4 . . ?
C23 C24 C17 114.0(5) . . ?
C23 C24 H24A 108.7 . . ?
C17 C24 H24A 108.7 . . ?
C23 C24 H24B 108.7 . . ?
C17 C24 H24B 108.7 . . ?
H24A C24 H24B 107.6 . . ?
C16 B1 C17 126.7(4) . . ?
C16 B1 C21 121.3(4) . . ?
C17 B1 C21 111.7(4) . . ?
C2 N1 C6 119.5(3) . . ?
C2 N1 Fe1 125.8(2) . . ?
C6 N1 Fe1 114.7(2) . . ?
C7 N2 N3 105.3(3) . . ?
C7 N2 Fe1 115.5(2) . . ?
N3 N2 Fe1 139.2(2) . . ?
N2 N3 C9 111.3(3) . . ?
N2 N3 C14 116.2(3) . . ?
C9 N3 C14 132.5(3) . . ?
N2 Fe1 N1 78.44(11) . . ?
N2 Fe1 Br2 115.25(9) . . ?
N1 Fe1 Br2 109.76(8) . . ?
N2 Fe1 Br1 107.62(9) . . ?
N1 Fe1 Br1 110.71(9) . . ?
Br2 Fe1 Br1 125.33(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 -1.2(6) . . . . ?
C1 C2 C3 C4 178.8(4) . . . . ?
C2 C3 C4 C5 2.5(6) . . . . ?
C3 C4 C5 C6 -1.3(6) . . . . ?
C4 C5 C6 N1 -1.2(6) . . . . ?
C4 C5 C6 C7 -179.8(4) . . . . ?
N1 C6 C7 N2 -3.2(5) . . . . ?
C5 C6 C7 N2 175.4(4) . . . . ?
N1 C6 C7 C8 -179.3(4) . . . . ?
C5 C6 C7 C8 -0.6(7) . . . . ?
N2 C7 C8 C9 -0.3(5) . . . . ?
C6 C7 C8 C9 176.0(4) . . . . ?
C7 C8 C9 N3 0.4(4) . . . . ?
C7 C8 C9 C10 -178.7(4) . . . . ?
N3 C9 C10 C11 175.7(4) . . . . ?
C8 C9 C10 C11 -5.3(6) . . . . ?
N3 C9 C10 C12 -65.9(5) . . . . ?
C8 C9 C10 C12 113.1(5) . . . . ?
N3 C9 C10 C13 57.9(5) . . . . ?
C8 C9 C10 C13 -123.1(5) . . . . ?
N3 C14 C15 C16 174.3(3) . . . . ?
C14 C15 C16 B1 173.5(4) . . . . ?
C24 C17 C18 C19 61.5(7) . . . . ?
B1 C17 C18 C19 -58.0(6) . . . . ?
C17 C18 C19 C20 52.2(7) . . . . ?
C18 C19 C20 C21 -50.9(7) . . . . ?
C19 C20 C21 C22 -63.5(6) . . . . ?
C19 C20 C21 B1 56.4(5) . . . . ?
C20 C21 C22 C23 112.2(6) . . . . ?
B1 C21 C22 C23 -4.2(6) . . . . ?
C21 C22 C23 C24 -47.9(7) . . . . ?
C22 C23 C24 C17 49.6(7) . . . . ?
C18 C17 C24 C23 -111.9(6) . . . . ?
B1 C17 C24 C23 1.7(7) . . . . ?
C15 C16 B1 C17 1.0(7) . . . . ?
C15 C16 B1 C21 -172.6(4) . . . . ?
C24 C17 B1 C16 133.4(5) . . . . ?
C18 C17 B1 C16 -106.5(5) . . . . ?
C24 C17 B1 C21 -52.5(6) . . . . ?
C18 C17 B1 C21 67.7(5) . . . . ?
C20 C21 B1 C16 106.0(5) . . . . ?
C22 C21 B1 C16 -132.3(5) . . . . ?
C20 C21 B1 C17 -68.5(5) . . . . ?
C22 C21 B1 C17 53.2(5) . . . . ?
C3 C2 N1 C6 -1.2(5) . . . . ?
C1 C2 N1 C6 178.8(4) . . . . ?
C3 C2 N1 Fe1 176.6(3) . . . . ?
C1 C2 N1 Fe1 -3.3(5) . . . . ?
C5 C6 N1 C2 2.5(6) . . . . ?
C7 C6 N1 C2 -178.9(3) . . . . ?
C5 C6 N1 Fe1 -175.6(3) . . . . ?
C7 C6 N1 Fe1 3.1(4) . . . . ?
C8 C7 N2 N3 0.0(4) . . . . ?
C6 C7 N2 N3 -176.9(3) . . . . ?
C8 C7 N2 Fe1 178.6(3) . . . . ?
C6 C7 N2 Fe1 1.7(4) . . . . ?
C7 N2 N3 C9 0.3(4) . . . . ?
Fe1 N2 N3 C9 -177.8(3) . . . . ?
C7 N2 N3 C14 179.9(3) . . . . ?
Fe1 N2 N3 C14 1.8(5) . . . . ?
C8 C9 N3 N2 -0.5(4) . . . . ?
C10 C9 N3 N2 178.7(3) . . . . ?
C8 C9 N3 C14 -180.0(4) . . . . ?
C10 C9 N3 C14 -0.8(7) . . . . ?
C15 C14 N3 N2 75.4(4) . . . . ?
C15 C14 N3 C9 -105.1(5) . . . . ?

_refine_diff_density_max         1.938
_refine_diff_density_min         -1.011
_refine_diff_density_rms         0.144



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_JK526_0m
_database_code_depnum_ccdc_archive 'CCDC 1941366'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller '
;Purdue University
United States of America
;
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H54 B Fe N5 O'
_chemical_formula_weight         687.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   11.0311(5)
_cell_length_b                   14.6748(6)
_cell_length_c                   22.6949(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.0876(19)
_cell_angle_gamma                90
_cell_volume                     3637.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9322
_cell_measurement_theta_min      2.3259
_cell_measurement_theta_max      30.5659

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_F_000             1472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.453
_shelx_estimated_absorpt_T_min   0.822
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6868
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            44978
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.283
_diffrn_reflns_theta_max         30.560
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             10246
_reflns_number_gt                7654
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Apex3 v2018.1-0 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev946 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0504P)²+1.7586P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10246
_refine_ls_number_parameters     437
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.1131
_refine_ls_wR_factor_gt          0.1004
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.44910(17) 0.48797(12) 0.58960(9) 0.0334(4) Uani 1 1 d . . . . .
H1A H 0.521672 0.448844 0.592295 0.050 Uiso 1 1 calc R U . . .
H1B H 0.405628 0.476168 0.623625 0.050 Uiso 1 1 calc R U . . .
H1C H 0.474287 0.552029 0.589920 0.050 Uiso 1 1 calc R U . . .
C2 C 0.36637(15) 0.46794(10) 0.53315(8) 0.0245(3) Uani 1 1 d . . . . .
C3 C 0.31169(16) 0.53696(11) 0.49691(9) 0.0307(4) Uani 1 1 d . . . . .
H3 H 0.327412 0.598921 0.507468 0.037 Uiso 1 1 calc R U . . .
C4 C 0.23453(17) 0.51556(11) 0.44559(9) 0.0343(4) Uani 1 1 d . . . . .
H4 H 0.197769 0.562456 0.420274 0.041 Uiso 1 1 calc R U . . .
C5 C 0.21118(16) 0.42450(11) 0.43133(8) 0.0286(4) Uani 1 1 d . . . . .
H5 H 0.157932 0.407984 0.396359 0.034 Uiso 1 1 calc R U . . .
C6 C 0.26741(14) 0.35849(10) 0.46933(7) 0.0195(3) Uani 1 1 d . . . . .
C7 C 0.24705(13) 0.26074(9) 0.45794(7) 0.0176(3) Uani 1 1 d . . . . .
C8 C 0.17380(13) 0.21502(10) 0.41271(7) 0.0193(3) Uani 1 1 d . . . . .
H8 H 0.119947 0.241252 0.380870 0.023 Uiso 1 1 calc R U . . .
C9 C 0.19558(13) 0.12270(9) 0.42367(7) 0.0172(3) Uani 1 1 d . . . . .
C10 C 0.14099(14) 0.04260(10) 0.38729(7) 0.0209(3) Uani 1 1 d . . . . .
C11 C 0.24056(16) -0.02090(11) 0.36906(8) 0.0285(4) Uani 1 1 d . . . . .
H11A H 0.202245 -0.067726 0.341784 0.043 Uiso 1 1 calc R U . . .
H11B H 0.284647 -0.050095 0.404602 0.043 Uiso 1 1 calc R U . . .
H11C H 0.298118 0.014735 0.349193 0.043 Uiso 1 1 calc R U . . .
C12 C 0.05273(15) -0.01078(11) 0.42130(8) 0.0274(3) Uani 1 1 d . . . . .
H12A H -0.010388 0.030492 0.432147 0.041 Uiso 1 1 calc R U . . .
H12B H 0.098433 -0.037109 0.457458 0.041 Uiso 1 1 calc R U . . .
H12C H 0.013938 -0.059714 0.395953 0.041 Uiso 1 1 calc R U . . .
C13 C 0.06688(16) 0.08013(12) 0.33010(8) 0.0300(4) Uani 1 1 d . . . . .
H13A H 0.121340 0.114029 0.307418 0.045 Uiso 1 1 calc R U . . .
H13B H 0.002669 0.120848 0.340432 0.045 Uiso 1 1 calc R U . . .
H13C H 0.029339 0.029480 0.305962 0.045 Uiso 1 1 calc R U . . .
C14 C 0.33857(14) 0.03695(10) 0.50443(7) 0.0222(3) Uani 1 1 d . . . . .
H14A H 0.406701 0.018070 0.483031 0.027 Uiso 1 1 calc R U . . .
H14B H 0.279245 -0.013987 0.502154 0.027 Uiso 1 1 calc R U . . .
C15 C 0.38874(14) 0.05437(10) 0.56944(7) 0.0212(3) Uani 1 1 d . . . . .
H15A H 0.448957 0.104696 0.571472 0.025 Uiso 1 1 calc R U . . .
H15B H 0.432737 -0.000816 0.585907 0.025 Uiso 1 1 calc R U . . .
C16 C 0.29089(14) 0.07887(11) 0.60862(7) 0.0237(3) Uani 1 1 d . . . . .
H16A H 0.259192 0.021295 0.623316 0.028 Uiso 1 1 calc R U . . .
H16B H 0.222059 0.108491 0.582966 0.028 Uiso 1 1 calc R U . . .
C17 C 0.46196(15) 0.12441(12) 0.70662(8) 0.0280(3) Uani 1 1 d . . . . .
H17 H 0.527725 0.130555 0.680715 0.034 Uiso 1 1 calc R U . . .
C18 C 0.46147(17) 0.02574(14) 0.72852(10) 0.0388(4) Uani 1 1 d . . . . .
H18A H 0.455568 -0.015377 0.693652 0.047 Uiso 1 1 calc R U . . .
H18B H 0.540513 0.013243 0.753702 0.047 Uiso 1 1 calc R U . . .
C19 C 0.3576(2) 0.00302(18) 0.76412(11) 0.0515(6) Uani 1 1 d . . . . .
H19A H 0.379334 0.026933 0.805029 0.062 Uiso 1 1 calc R U . . .
H19B H 0.351187 -0.064079 0.766998 0.062 Uiso 1 1 calc R U . . .
C20 C 0.23103(18) 0.04111(16) 0.73817(9) 0.0415(5) Uani 1 1 d . . . . .
H20A H 0.177921 0.040313 0.769888 0.050 Uiso 1 1 calc R U . . .
H20B H 0.193997 -0.000428 0.706245 0.050 Uiso 1 1 calc R U . . .
C21 C 0.23057(16) 0.13861(14) 0.71246(8) 0.0322(4) Uani 1 1 d . . . . .
H21 H 0.147721 0.150215 0.689595 0.039 Uiso 1 1 calc R U . . .
C22 C 0.25476(19) 0.21153(17) 0.76085(9) 0.0432(5) Uani 1 1 d . . . . .
H22A H 0.194452 0.204104 0.788935 0.052 Uiso 1 1 calc R U . . .
H22B H 0.241282 0.272254 0.742069 0.052 Uiso 1 1 calc R U . . .
C23 C 0.3842(2) 0.2089(2) 0.79623(9) 0.0515(6) Uani 1 1 d . . . . .
H23A H 0.387742 0.159227 0.825966 0.062 Uiso 1 1 calc R U . . .
H23B H 0.399296 0.266940 0.818230 0.062 Uiso 1 1 calc R U . . .
C24 C 0.48772(18) 0.19414(16) 0.75803(9) 0.0394(5) Uani 1 1 d . . . . .
H24A H 0.561875 0.174185 0.784618 0.047 Uiso 1 1 calc R U . . .
H24B H 0.506711 0.253592 0.740852 0.047 Uiso 1 1 calc R U . . .
C25 C 0.64437(14) 0.22506(9) 0.50076(8) 0.0235(3) Uani 1 1 d . . . . .
C26 C 0.58050(16) 0.20800(11) 0.44420(8) 0.0286(4) Uani 1 1 d . . . . .
H26 H 0.493638 0.211071 0.437262 0.034 Uiso 1 1 calc R U . . .
C27 C 0.64636(19) 0.18652(12) 0.39849(9) 0.0354(4) Uani 1 1 d . . . . .
H27 H 0.603819 0.174925 0.359852 0.043 Uiso 1 1 calc R U . . .
C28 C 0.7741(2) 0.18153(13) 0.40798(10) 0.0424(5) Uani 1 1 d . . . . .
H28 H 0.816903 0.165863 0.375922 0.051 Uiso 1 1 calc R U . . .
C29 C 0.83837(18) 0.19900(12) 0.46311(11) 0.0393(5) Uani 1 1 d . . . . .
H29 H 0.925250 0.195897 0.469254 0.047 Uiso 1 1 calc R U . . .
C30 C 0.77437(15) 0.22145(10) 0.51012(9) 0.0295(4) Uani 1 1 d . . . . .
C31 C 0.81093(15) 0.24563(10) 0.57131(10) 0.0298(4) Uani 1 1 d . . . . .
C32 C 0.92385(17) 0.25582(12) 0.60765(12) 0.0411(5) Uani 1 1 d . . . . .
H32 H 0.998142 0.245280 0.592051 0.049 Uiso 1 1 calc R U . . .
C33 C 0.92600(18) 0.28121(13) 0.66605(12) 0.0490(6) Uani 1 1 d . . . . .
H33 H 1.002300 0.287843 0.690908 0.059 Uiso 1 1 calc R U . . .
C34 C 0.81736(19) 0.29736(13) 0.68930(11) 0.0441(5) Uani 1 1 d . . . . .
H34 H 0.821019 0.315280 0.729731 0.053 Uiso 1 1 calc R U . . .
C35 C 0.70386(17) 0.28774(12) 0.65444(9) 0.0338(4) Uani 1 1 d . . . . .
H35 H 0.630276 0.298651 0.670590 0.041 Uiso 1 1 calc R U . . .
C36 C 0.70089(14) 0.26173(10) 0.59533(8) 0.0254(3) Uani 1 1 d . . . . .
C40 C 0.8898(2) 0.40557(16) 0.39859(12) 0.0521(6) Uani 1 1 d . . . . .
H40A H 0.938919 0.397319 0.438218 0.063 Uiso 1 1 calc R U . . .
H40B H 0.805920 0.382512 0.400073 0.063 Uiso 1 1 calc R U . . .
C41 C 0.8868(2) 0.50450(16) 0.38051(12) 0.0500(6) Uani 1 1 d . . . . .
H41A H 0.814747 0.535840 0.392660 0.060 Uiso 1 1 calc R U . . .
H41B H 0.962097 0.536450 0.398369 0.060 Uiso 1 1 calc R U . . .
C44 C 0.8783(3) 0.5006(2) 0.31369(13) 0.0738(8) Uani 1 1 d . . . . .
H44A H 0.943925 0.537473 0.299847 0.089 Uiso 1 1 calc R U . . .
H44B H 0.797994 0.523617 0.294522 0.089 Uiso 1 1 calc R U . . .
C45 C 0.8934(2) 0.40026(18) 0.29928(12) 0.0561(6) Uani 1 1 d . . . . .
H45A H 0.813128 0.372529 0.284303 0.067 Uiso 1 1 calc R U . . .
H45B H 0.948390 0.392936 0.268700 0.067 Uiso 1 1 calc R U . . .
B1 B 0.33071(17) 0.14507(13) 0.66612(8) 0.0242(4) Uani 1 1 d . . . . .
N1 N 0.34473(11) 0.37921(8) 0.51932(6) 0.0202(3) Uani 1 1 d . . . . .
N2 N 0.31023(11) 0.20172(8) 0.49548(6) 0.0181(2) Uani 1 1 d . . . . .
N3 N 0.27759(11) 0.11745(8) 0.47436(6) 0.0170(2) Uani 1 1 d . . . . .
N4 N 0.33585(14) 0.24757(9) 0.63821(7) 0.0272(3) Uani 1 1 d . . . . .
H4A H 0.372838 0.285067 0.667259 0.033 Uiso 1 1 calc R U . . .
H4B H 0.257639 0.267686 0.628168 0.033 Uiso 1 1 calc R U . . .
N5 N 0.59849(12) 0.24930(8) 0.55296(7) 0.0224(3) Uani 1 1 d . . . . .
Fe1 Fe 0.42417(2) 0.26055(2) 0.56574(2) 0.01894(7) Uani 1 1 d . . . . .
O1 O 0.94507(14) 0.35877(10) 0.35373(7) 0.0480(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 1.494(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 N1 1.3528(19) . ?
C2 C3 1.388(2) . ?
C3 C4 1.379(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(2) . ?
C5 H5 0.9500 . ?
C6 N1 1.355(2) . ?
C6 C7 1.4693(19) . ?
C7 N2 1.3396(19) . ?
C7 C8 1.387(2) . ?
C8 C9 1.392(2) . ?
C8 H8 0.9500 . ?
C9 N3 1.3618(19) . ?
C9 C10 1.512(2) . ?
C10 C13 1.535(2) . ?
C10 C12 1.539(2) . ?
C10 C11 1.541(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 N3 1.4781(18) . ?
C14 C15 1.523(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.535(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 B1 1.637(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.531(3) . ?
C17 C24 1.548(3) . ?
C17 B1 1.630(2) . ?
C17 H17 1.0000 . ?
C18 C19 1.529(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.541(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.545(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.530(3) . ?
C21 B1 1.632(3) . ?
C21 H21 1.0000 . ?
C22 C23 1.537(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.543(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.397(3) . ?
C25 N5 1.398(2) . ?
C25 C30 1.421(2) . ?
C26 C27 1.384(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.397(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.373(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.399(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.435(3) . ?
C31 C32 1.402(3) . ?
C31 C36 1.419(2) . ?
C32 C33 1.374(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.396(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.391(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.391(3) . ?
C35 H35 0.9500 . ?
C36 N5 1.389(2) . ?
C40 O1 1.434(3) . ?
C40 C41 1.508(3) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 C44 1.507(4) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C44 C45 1.522(4) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 O1 1.423(3) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
B1 N4 1.636(2) . ?
N1 Fe1 2.1564(13) . ?
N2 N3 1.3566(16) . ?
N2 Fe1 2.0746(13) . ?
N4 Fe1 2.0351(14) . ?
N4 H4A 0.9100 . ?
N4 H4B 0.9100 . ?
N5 Fe1 1.9915(13) . ?

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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 121.14(16) . . ?
N1 C2 C1 117.06(15) . . ?
C3 C2 C1 121.79(14) . . ?
C4 C3 C2 119.97(15) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 119.19(16) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 118.39(16) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
N1 C6 C5 122.61(14) . . ?
N1 C6 C7 115.41(13) . . ?
C5 C6 C7 121.98(14) . . ?
N2 C7 C8 110.78(12) . . ?
N2 C7 C6 117.80(13) . . ?
C8 C7 C6 131.39(14) . . ?
C7 C8 C9 105.70(13) . . ?
C7 C8 H8 127.2 . . ?
C9 C8 H8 127.2 . . ?
N3 C9 C8 106.46(12) . . ?
N3 C9 C10 125.70(13) . . ?
C8 C9 C10 127.84(14) . . ?
C9 C10 C13 107.85(13) . . ?
C9 C10 C12 110.69(13) . . ?
C13 C10 C12 107.90(13) . . ?
C9 C10 C11 111.88(12) . . ?
C13 C10 C11 107.75(14) . . ?
C12 C10 C11 110.61(13) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C15 113.13(12) . . ?
N3 C14 H14A 109.0 . . ?
C15 C14 H14A 109.0 . . ?
N3 C14 H14B 109.0 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 C16 114.29(13) . . ?
C14 C15 H15A 108.7 . . ?
C16 C15 H15A 108.7 . . ?
C14 C15 H15B 108.7 . . ?
C16 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C15 C16 B1 117.99(13) . . ?
C15 C16 H16A 107.8 . . ?
B1 C16 H16A 107.8 . . ?
C15 C16 H16B 107.8 . . ?
B1 C16 H16B 107.8 . . ?
H16A C16 H16B 107.1 . . ?
C18 C17 C24 112.89(16) . . ?
C18 C17 B1 108.39(14) . . ?
C24 C17 B1 110.87(14) . . ?
C18 C17 H17 108.2 . . ?
C24 C17 H17 108.2 . . ?
B1 C17 H17 108.2 . . ?
C19 C18 C17 114.50(18) . . ?
C19 C18 H18A 108.6 . . ?
C17 C18 H18A 108.6 . . ?
C19 C18 H18B 108.6 . . ?
C17 C18 H18B 108.6 . . ?
H18A C18 H18B 107.6 . . ?
C18 C19 C20 115.15(17) . . ?
C18 C19 H19A 108.5 . . ?
C20 C19 H19A 108.5 . . ?
C18 C19 H19B 108.5 . . ?
C20 C19 H19B 108.5 . . ?
H19A C19 H19B 107.5 . . ?
C19 C20 C21 115.77(16) . . ?
C19 C20 H20A 108.3 . . ?
C21 C20 H20A 108.3 . . ?
C19 C20 H20B 108.3 . . ?
C21 C20 H20B 108.3 . . ?
H20A C20 H20B 107.4 . . ?
C22 C21 C20 112.69(17) . . ?
C22 C21 B1 110.89(15) . . ?
C20 C21 B1 109.31(15) . . ?
C22 C21 H21 107.9 . . ?
C20 C21 H21 107.9 . . ?
B1 C21 H21 107.9 . . ?
C21 C22 C23 114.37(18) . . ?
C21 C22 H22A 108.7 . . ?
C23 C22 H22A 108.7 . . ?
C21 C22 H22B 108.7 . . ?
C23 C22 H22B 108.7 . . ?
H22A C22 H22B 107.6 . . ?
C22 C23 C24 114.62(17) . . ?
C22 C23 H23A 108.6 . . ?
C24 C23 H23A 108.6 . . ?
C22 C23 H23B 108.6 . . ?
C24 C23 H23B 108.6 . . ?
H23A C23 H23B 107.6 . . ?
C23 C24 C17 116.38(17) . . ?
C23 C24 H24A 108.2 . . ?
C17 C24 H24A 108.2 . . ?
C23 C24 H24B 108.2 . . ?
C17 C24 H24B 108.2 . . ?
H24A C24 H24B 107.3 . . ?
C26 C25 N5 128.92(15) . . ?
C26 C25 C30 119.90(16) . . ?
N5 C25 C30 111.16(16) . . ?
C27 C26 C25 118.65(17) . . ?
C27 C26 H26 120.7 . . ?
C25 C26 H26 120.7 . . ?
C26 C27 C28 121.4(2) . . ?
C26 C27 H27 119.3 . . ?
C28 C27 H27 119.3 . . ?
C29 C28 C27 120.76(19) . . ?
C29 C28 H28 119.6 . . ?
C27 C28 H28 119.6 . . ?
C28 C29 C30 119.18(18) . . ?
C28 C29 H29 120.4 . . ?
C30 C29 H29 120.4 . . ?
C29 C30 C25 120.12(19) . . ?
C29 C30 C31 133.86(17) . . ?
C25 C30 C31 106.01(15) . . ?
C32 C31 C36 119.6(2) . . ?
C32 C31 C30 134.52(19) . . ?
C36 C31 C30 105.89(15) . . ?
C33 C32 C31 119.3(2) . . ?
C33 C32 H32 120.3 . . ?
C31 C32 H32 120.3 . . ?
C32 C33 C34 120.76(18) . . ?
C32 C33 H33 119.6 . . ?
C34 C33 H33 119.6 . . ?
C35 C34 C33 121.3(2) . . ?
C35 C34 H34 119.3 . . ?
C33 C34 H34 119.3 . . ?
C36 C35 C34 118.27(19) . . ?
C36 C35 H35 120.9 . . ?
C34 C35 H35 120.9 . . ?
N5 C36 C35 127.62(16) . . ?
N5 C36 C31 111.63(16) . . ?
C35 C36 C31 120.74(16) . . ?
O1 C40 C41 105.27(18) . . ?
O1 C40 H40A 110.7 . . ?
C41 C40 H40A 110.7 . . ?
O1 C40 H40B 110.7 . . ?
C41 C40 H40B 110.7 . . ?
H40A C40 H40B 108.8 . . ?
C44 C41 C40 103.5(2) . . ?
C44 C41 H41A 111.1 . . ?
C40 C41 H41A 111.1 . . ?
C44 C41 H41B 111.1 . . ?
C40 C41 H41B 111.1 . . ?
H41A C41 H41B 109.0 . . ?
C41 C44 C45 105.1(2) . . ?
C41 C44 H44A 110.7 . . ?
C45 C44 H44A 110.7 . . ?
C41 C44 H44B 110.7 . . ?
C45 C44 H44B 110.7 . . ?
H44A C44 H44B 108.8 . . ?
O1 C45 C44 105.7(2) . . ?
O1 C45 H45A 110.6 . . ?
C44 C45 H45A 110.6 . . ?
O1 C45 H45B 110.6 . . ?
C44 C45 H45B 110.6 . . ?
H45A C45 H45B 108.7 . . ?
C17 B1 C21 104.71(14) . . ?
C17 B1 N4 108.22(14) . . ?
C21 B1 N4 111.49(14) . . ?
C17 B1 C16 117.16(14) . . ?
C21 B1 C16 110.45(14) . . ?
N4 B1 C16 104.90(13) . . ?
C2 N1 C6 118.70(14) . . ?
C2 N1 Fe1 128.14(11) . . ?
C6 N1 Fe1 113.12(9) . . ?
C7 N2 N3 106.03(12) . . ?
C7 N2 Fe1 115.12(9) . . ?
N3 N2 Fe1 138.85(10) . . ?
N2 N3 C9 111.02(11) . . ?
N2 N3 C14 118.98(12) . . ?
C9 N3 C14 129.81(12) . . ?
B1 N4 Fe1 116.46(10) . . ?
B1 N4 H4A 108.2 . . ?
Fe1 N4 H4A 108.2 . . ?
B1 N4 H4B 108.2 . . ?
Fe1 N4 H4B 108.2 . . ?
H4A N4 H4B 107.3 . . ?
C36 N5 C25 105.31(13) . . ?
C36 N5 Fe1 126.61(12) . . ?
C25 N5 Fe1 128.07(11) . . ?
N5 Fe1 N4 133.77(6) . . ?
N5 Fe1 N2 110.28(5) . . ?
N4 Fe1 N2 105.97(6) . . ?
N5 Fe1 N1 109.28(5) . . ?
N4 Fe1 N1 105.23(5) . . ?
N2 Fe1 N1 78.45(5) . . ?
C45 O1 C40 104.66(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 -0.5(3) . . . . ?
C1 C2 C3 C4 -179.08(17) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 N1 -0.6(3) . . . . ?
C4 C5 C6 C7 179.47(16) . . . . ?
N1 C6 C7 N2 -3.3(2) . . . . ?
C5 C6 C7 N2 176.61(15) . . . . ?
N1 C6 C7 C8 178.71(15) . . . . ?
C5 C6 C7 C8 -1.4(3) . . . . ?
N2 C7 C8 C9 -0.59(17) . . . . ?
C6 C7 C8 C9 177.49(15) . . . . ?
C7 C8 C9 N3 0.92(16) . . . . ?
C7 C8 C9 C10 -178.84(14) . . . . ?
N3 C9 C10 C13 -172.72(14) . . . . ?
C8 C9 C10 C13 7.0(2) . . . . ?
N3 C9 C10 C12 69.46(19) . . . . ?
C8 C9 C10 C12 -110.83(17) . . . . ?
N3 C9 C10 C11 -54.4(2) . . . . ?
C8 C9 C10 C11 125.31(17) . . . . ?
N3 C14 C15 C16 62.05(17) . . . . ?
C14 C15 C16 B1 -150.34(13) . . . . ?
C24 C17 C18 C19 65.8(2) . . . . ?
B1 C17 C18 C19 -57.4(2) . . . . ?
C17 C18 C19 C20 43.4(3) . . . . ?
C18 C19 C20 C21 -40.1(3) . . . . ?
C19 C20 C21 C22 -72.8(2) . . . . ?
C19 C20 C21 B1 51.0(2) . . . . ?
C20 C21 C22 C23 66.6(2) . . . . ?
B1 C21 C22 C23 -56.3(2) . . . . ?
C21 C22 C23 C24 43.0(3) . . . . ?
C22 C23 C24 C17 -40.4(3) . . . . ?
C18 C17 C24 C23 -71.7(2) . . . . ?
B1 C17 C24 C23 50.2(2) . . . . ?
N5 C25 C26 C27 178.78(15) . . . . ?
C30 C25 C26 C27 0.9(2) . . . . ?
C25 C26 C27 C28 0.1(3) . . . . ?
C26 C27 C28 C29 -0.8(3) . . . . ?
C27 C28 C29 C30 0.4(3) . . . . ?
C28 C29 C30 C25 0.6(2) . . . . ?
C28 C29 C30 C31 -177.97(17) . . . . ?
C26 C25 C30 C29 -1.3(2) . . . . ?
N5 C25 C30 C29 -179.54(14) . . . . ?
C26 C25 C30 C31 177.65(14) . . . . ?
N5 C25 C30 C31 -0.58(16) . . . . ?
C29 C30 C31 C32 -0.3(3) . . . . ?
C25 C30 C31 C32 -179.04(17) . . . . ?
C29 C30 C31 C36 179.17(17) . . . . ?
C25 C30 C31 C36 0.42(16) . . . . ?
C36 C31 C32 C33 0.1(3) . . . . ?
C30 C31 C32 C33 179.46(18) . . . . ?
C31 C32 C33 C34 -0.4(3) . . . . ?
C32 C33 C34 C35 0.5(3) . . . . ?
C33 C34 C35 C36 -0.2(3) . . . . ?
C34 C35 C36 N5 -179.21(16) . . . . ?
C34 C35 C36 C31 -0.1(2) . . . . ?
C32 C31 C36 N5 179.42(14) . . . . ?
C30 C31 C36 N5 -0.14(17) . . . . ?
C32 C31 C36 C35 0.2(2) . . . . ?
C30 C31 C36 C35 -179.37(15) . . . . ?
O1 C40 C41 C44 28.8(3) . . . . ?
C40 C41 C44 C45 -6.9(3) . . . . ?
C41 C44 C45 O1 -17.2(3) . . . . ?
C18 C17 B1 C21 65.68(18) . . . . ?
C24 C17 B1 C21 -58.75(18) . . . . ?
C18 C17 B1 N4 -175.29(14) . . . . ?
C24 C17 B1 N4 60.28(18) . . . . ?
C18 C17 B1 C16 -57.0(2) . . . . ?
C24 C17 B1 C16 178.52(15) . . . . ?
C22 C21 B1 C17 62.55(19) . . . . ?
C20 C21 B1 C17 -62.28(18) . . . . ?
C22 C21 B1 N4 -54.3(2) . . . . ?
C20 C21 B1 N4 -179.08(14) . . . . ?
C22 C21 B1 C16 -170.47(15) . . . . ?
C20 C21 B1 C16 64.70(18) . . . . ?
C15 C16 B1 C17 -43.2(2) . . . . ?
C15 C16 B1 C21 -162.97(14) . . . . ?
C15 C16 B1 N4 76.78(16) . . . . ?
C3 C2 N1 C6 -0.5(2) . . . . ?
C1 C2 N1 C6 178.15(15) . . . . ?
C3 C2 N1 Fe1 176.94(12) . . . . ?
C1 C2 N1 Fe1 -4.4(2) . . . . ?
C5 C6 N1 C2 1.1(2) . . . . ?
C7 C6 N1 C2 -179.00(14) . . . . ?
C5 C6 N1 Fe1 -176.75(13) . . . . ?
C7 C6 N1 Fe1 3.18(16) . . . . ?
C8 C7 N2 N3 0.01(17) . . . . ?
C6 C7 N2 N3 -178.36(13) . . . . ?
C8 C7 N2 Fe1 -179.96(10) . . . . ?
C6 C7 N2 Fe1 1.68(17) . . . . ?
C7 N2 N3 C9 0.60(16) . . . . ?
Fe1 N2 N3 C9 -179.44(11) . . . . ?
C7 N2 N3 C14 176.11(13) . . . . ?
Fe1 N2 N3 C14 -3.9(2) . . . . ?
C8 C9 N3 N2 -0.97(16) . . . . ?
C10 C9 N3 N2 178.80(13) . . . . ?
C8 C9 N3 C14 -175.85(14) . . . . ?
C10 C9 N3 C14 3.9(2) . . . . ?
C15 C14 N3 N2 25.17(19) . . . . ?
C15 C14 N3 C9 -160.30(14) . . . . ?
C17 B1 N4 Fe1 79.53(15) . . . . ?
C21 B1 N4 Fe1 -165.82(11) . . . . ?
C16 B1 N4 Fe1 -46.27(15) . . . . ?
C35 C36 N5 C25 178.96(16) . . . . ?
C31 C36 N5 C25 -0.21(16) . . . . ?
C35 C36 N5 Fe1 -2.6(2) . . . . ?
C31 C36 N5 Fe1 178.20(10) . . . . ?
C26 C25 N5 C36 -177.53(15) . . . . ?
C30 C25 N5 C36 0.49(16) . . . . ?
C26 C25 N5 Fe1 4.1(2) . . . . ?
C30 C25 N5 Fe1 -177.89(10) . . . . ?
C44 C45 O1 C40 35.9(3) . . . . ?
C41 C40 O1 C45 -40.9(2) . . . . ?

_refine_diff_density_max         0.493
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.061


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_jk4287_0m
_database_code_depnum_ccdc_archive 'CCDC 1941374'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller '
;Purdue University
United States of America
;
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H40 B Br2 N5 Zn'
_chemical_formula_weight         634.61

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   33.5220(13)
_cell_length_b                   12.4233(5)
_cell_length_c                   13.6832(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.838(2)
_cell_angle_gamma                90
_cell_volume                     5668.9(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9883
_cell_measurement_theta_min      3.7981
_cell_measurement_theta_max      72.2307

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_F_000             2592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    4.654
_shelx_estimated_absorpt_T_min   0.234
_shelx_estimated_absorpt_T_max   0.913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.488834
_exptl_absorpt_correction_T_max  0.753554
_exptl_absorpt_process_details   
;
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.
(2015). J. Appl. Cryst. 48 3-10.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34319
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.797
_diffrn_reflns_theta_max         72.199
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             5264
_reflns_number_gt                4801
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Apex3 v2017.3-0 (Bruker, 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev937 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
The crystal under investigation was found to be non-merohedrally 
twinned. The orientation matrices for the two components were 
identified using the program Cell_Now, with the two components 
being related by a 180 degree rotation around the reciprocal 
a-axis. The two components were integrated using Saint and 
corrected for absorption using twinabs, resulting in the 
following statistics:

12910 data (4106 unique) involve domain 1 only, mean I/sigma 29.8
12775 data (4089 unique) involve domain 2 only, mean I/sigma 11.3
 8796 data (2903 unique) involve 2 domains, mean I/sigma 35.6

The exact twin matrix identified by the integration program was 
found to be: 

 0.99992 -0.00327  0.50349
-0.00043 -1.00000 -0.00079
 0.00033  0.00083 -0.99992

The structure was solved using direct methods with only the 
non-overlapping reflections of component 1. The structure was 
refined using the hklf 5 routine with all reflections of component 
1 (including the overlapping ones), resulting in a BASF value of 
0.177(1).

The Rint value given is for all reflections and is based on 
agreement between observed single and composite intensities 
and those calculated from refined unique intensities and twin 
fractions (TWINABS (Sheldrick, 2012)).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0717P)²+1.6459P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5264
_refine_ls_number_parameters     309
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.1102
_refine_ls_wR_factor_gt          0.1014
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.134
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.21445(13) -0.1232(3) 0.5773(4) 0.0435(10) Uani 1 1 d . . . . .
H1A H 0.188781 -0.161070 0.565163 0.065 Uiso 1 1 calc R U . . .
H1B H 0.216821 -0.092143 0.643511 0.065 Uiso 1 1 calc R U . . .
H1C H 0.236481 -0.173956 0.571823 0.065 Uiso 1 1 calc R U . . .
C2 C 0.21637(10) -0.0351(3) 0.5032(3) 0.0307(7) Uani 1 1 d . . . . .
C3 C 0.18604(10) -0.0194(3) 0.4274(3) 0.0336(8) Uani 1 1 d . . . . .
H3 H 0.163537 -0.066235 0.420318 0.040 Uiso 1 1 calc R U . . .
C4 C 0.18882(9) 0.0646(3) 0.3625(3) 0.0302(7) Uani 1 1 d . . . . .
H4 H 0.167707 0.077475 0.312132 0.036 Uiso 1 1 calc R U . . .
C5 C 0.22248(10) 0.1304(3) 0.3709(3) 0.0264(7) Uani 1 1 d . . . . .
H5 H 0.224895 0.188649 0.326879 0.032 Uiso 1 1 calc R U . . .
C6 C 0.25244(10) 0.1082(2) 0.4456(3) 0.0248(7) Uani 1 1 d . . . . .
C7 C 0.29114(9) 0.1640(2) 0.4557(3) 0.0234(6) Uani 1 1 d . . . . .
C8 C 0.30841(9) 0.2378(2) 0.3953(3) 0.0245(6) Uani 1 1 d . . . . .
H8 H 0.296011 0.271281 0.337555 0.029 Uiso 1 1 calc R U . . .
C9 C 0.34775(10) 0.2520(2) 0.4378(3) 0.0244(6) Uani 1 1 d . . . . .
C10 C 0.38104(10) 0.3187(3) 0.4003(3) 0.0286(7) Uani 1 1 d . . . . .
C11 C 0.36264(13) 0.3878(3) 0.3142(3) 0.0405(9) Uani 1 1 d . . . . .
H11A H 0.383805 0.429637 0.287535 0.061 Uiso 1 1 calc R U . . .
H11B H 0.342726 0.436809 0.337409 0.061 Uiso 1 1 calc R U . . .
H11C H 0.349642 0.340943 0.262850 0.061 Uiso 1 1 calc R U . . .
C12 C 0.41273(11) 0.2443(3) 0.3619(3) 0.0342(8) Uani 1 1 d . . . . .
H12A H 0.400172 0.200613 0.307586 0.051 Uiso 1 1 calc R U . . .
H12B H 0.424006 0.197059 0.414985 0.051 Uiso 1 1 calc R U . . .
H12C H 0.434176 0.288071 0.338547 0.051 Uiso 1 1 calc R U . . .
C13 C 0.40091(11) 0.3943(3) 0.4802(3) 0.0348(8) Uani 1 1 d . . . . .
H13A H 0.421504 0.437658 0.452761 0.052 Uiso 1 1 calc R U . . .
H13B H 0.413292 0.351520 0.535343 0.052 Uiso 1 1 calc R U . . .
H13C H 0.380554 0.441993 0.503408 0.052 Uiso 1 1 calc R U . . .
C14 C 0.38719(9) 0.1598(3) 0.5876(3) 0.0270(7) Uani 1 1 d . . . . .
H14A H 0.411405 0.191127 0.562871 0.032 Uiso 1 1 calc R U . . .
H14B H 0.390110 0.080493 0.587052 0.032 Uiso 1 1 calc R U . . .
C15 C 0.38505(10) 0.1967(3) 0.6920(3) 0.0284(7) Uani 1 1 d . . . . .
H15A H 0.358748 0.176378 0.713503 0.034 Uiso 1 1 calc R U . . .
H15B H 0.387367 0.276114 0.695194 0.034 Uiso 1 1 calc R U . . .
C16 C 0.41870(9) 0.1460(3) 0.7613(3) 0.0277(7) Uani 1 1 d . . . . .
H16A H 0.444645 0.171756 0.741568 0.033 Uiso 1 1 calc R U . . .
H16B H 0.417789 0.067106 0.751161 0.033 Uiso 1 1 calc R U . . .
C17 C 0.42046(10) 0.2950(3) 0.9104(3) 0.0291(7) Uani 1 1 d . . . . .
H17 H 0.397359 0.333648 0.873962 0.035 Uiso 1 1 calc R U . . .
C18 C 0.41739(11) 0.3086(3) 1.0208(3) 0.0346(8) Uani 1 1 d . . . . .
H18A H 0.389688 0.290688 1.034168 0.041 Uiso 1 1 calc R U . . .
H18B H 0.421984 0.385386 1.037956 0.041 Uiso 1 1 calc R U . . .
C19 C 0.44666(13) 0.2401(3) 1.0891(3) 0.0387(8) Uani 1 1 d . . . . .
H19A H 0.473501 0.274031 1.093830 0.046 Uiso 1 1 calc R U . . .
H19B H 0.437567 0.240043 1.155754 0.046 Uiso 1 1 calc R U . . .
C20 C 0.45038(11) 0.1231(3) 1.0550(3) 0.0346(8) Uani 1 1 d . . . . .
H20A H 0.474078 0.090229 1.092708 0.041 Uiso 1 1 calc R U . . .
H20B H 0.426431 0.082807 1.071195 0.041 Uiso 1 1 calc R U . . .
C21 C 0.45445(10) 0.1094(3) 0.9451(3) 0.0288(7) Uani 1 1 d . . . . .
H21 H 0.453418 0.030804 0.929386 0.035 Uiso 1 1 calc R U . . .
C22 C 0.49422(10) 0.1554(3) 0.9150(3) 0.0343(8) Uani 1 1 d . . . . .
H22A H 0.516525 0.125841 0.960018 0.041 Uiso 1 1 calc R U . . .
H22B H 0.497781 0.129146 0.848077 0.041 Uiso 1 1 calc R U . . .
C23 C 0.49775(11) 0.2788(3) 0.9153(3) 0.0376(8) Uani 1 1 d . . . . .
H23A H 0.519350 0.299152 0.874597 0.045 Uiso 1 1 calc R U . . .
H23B H 0.506183 0.302462 0.983376 0.045 Uiso 1 1 calc R U . . .
C24 C 0.45949(11) 0.3415(3) 0.8775(3) 0.0345(8) Uani 1 1 d . . . . .
H24A H 0.462369 0.416900 0.900682 0.041 Uiso 1 1 calc R U . . .
H24B H 0.457247 0.342733 0.804843 0.041 Uiso 1 1 calc R U . . .
B1 B 0.41816(10) 0.1690(3) 0.8780(3) 0.0256(7) Uani 1 1 d . . . . .
N1 N 0.24890(8) 0.0288(2) 0.5118(2) 0.0256(6) Uani 1 1 d . . . . .
N2 N 0.31758(8) 0.1363(2) 0.5306(2) 0.0249(6) Uani 1 1 d . . . . .
N3 N 0.35180(7) 0.1900(2) 0.5204(2) 0.0232(5) Uani 1 1 d . . . . .
N4 N 0.37486(9) 0.1219(2) 0.9070(2) 0.0291(6) Uani 1 1 d . . . . .
H4A H 0.372466 0.138040 0.971037 0.035 Uiso 1 1 calc R U . . .
H4B H 0.354713 0.156274 0.869812 0.035 Uiso 1 1 calc R U . . .
N5 N 0.36968(9) 0.0068(3) 0.8935(3) 0.0346(6) Uani 1 1 d D . . . .
H5A H 0.3827(14) -0.014(4) 0.842(3) 0.052 Uiso 1 1 d D U . . .
H5B H 0.3430(7) -0.002(5) 0.872(4) 0.052 Uiso 1 1 d D U . . .
Zn1 Zn 0.29627(2) 0.02466(3) 0.62169(4) 0.02562(13) Uani 1 1 d . . . . .
Br1 Br 0.27681(2) 0.09948(3) 0.76953(3) 0.03009(11) Uani 1 1 d . . . . .
Br2 Br 0.33339(2) -0.13525(3) 0.63656(3) 0.03845(13) 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 1.499(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 N1 1.344(4) . ?
C2 C3 1.390(5) . ?
C3 C4 1.379(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(5) . ?
C5 H5 0.9500 . ?
C6 N1 1.352(4) . ?
C6 C7 1.465(4) . ?
C7 N2 1.330(4) . ?
C7 C8 1.400(5) . ?
C8 C9 1.397(4) . ?
C8 H8 0.9500 . ?
C9 N3 1.363(4) . ?
C9 C10 1.520(4) . ?
C10 C11 1.535(5) . ?
C10 C12 1.540(5) . ?
C10 C13 1.541(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 N3 1.474(4) . ?
C14 C15 1.510(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.533(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 B1 1.623(6) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.534(6) . ?
C17 C24 1.539(5) . ?
C17 B1 1.627(5) . ?
C17 H17 1.0000 . ?
C18 C19 1.541(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.535(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.533(6) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.544(5) . ?
C21 B1 1.627(5) . ?
C21 H21 1.0000 . ?
C22 C23 1.538(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.544(5) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
B1 N4 1.651(5) . ?
N1 Zn1 2.074(3) . ?
N2 N3 1.347(4) . ?
N2 Zn1 2.042(3) . ?
N4 N5 1.450(4) . ?
N4 H4A 0.9100 . ?
N4 H4B 0.9100 . ?
N5 H5A 0.90(2) . ?
N5 H5B 0.922(19) . ?
Zn1 Br2 2.3420(5) . ?
Zn1 Br1 2.3769(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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 120.5(3) . . ?
N1 C2 C1 117.5(3) . . ?
C3 C2 C1 121.9(3) . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 117.7(3) . . ?
C6 C5 H5 121.1 . . ?
C4 C5 H5 121.1 . . ?
N1 C6 C5 122.2(3) . . ?
N1 C6 C7 114.8(3) . . ?
C5 C6 C7 122.9(3) . . ?
N2 C7 C8 109.9(3) . . ?
N2 C7 C6 117.7(3) . . ?
C8 C7 C6 132.1(3) . . ?
C9 C8 C7 105.4(3) . . ?
C9 C8 H8 127.3 . . ?
C7 C8 H8 127.3 . . ?
N3 C9 C8 106.5(3) . . ?
N3 C9 C10 125.0(3) . . ?
C8 C9 C10 128.5(3) . . ?
C9 C10 C11 108.2(3) . . ?
C9 C10 C12 110.2(3) . . ?
C11 C10 C12 108.1(3) . . ?
C9 C10 C13 111.8(3) . . ?
C11 C10 C13 108.3(3) . . ?
C12 C10 C13 110.2(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C15 113.6(3) . . ?
N3 C14 H14A 108.8 . . ?
C15 C14 H14A 108.8 . . ?
N3 C14 H14B 108.8 . . ?
C15 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 C16 111.0(3) . . ?
C14 C15 H15A 109.4 . . ?
C16 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
C16 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C15 C16 B1 117.0(3) . . ?
C15 C16 H16A 108.0 . . ?
B1 C16 H16A 108.0 . . ?
C15 C16 H16B 108.0 . . ?
B1 C16 H16B 108.0 . . ?
H16A C16 H16B 107.3 . . ?
C18 C17 C24 113.0(3) . . ?
C18 C17 B1 111.6(3) . . ?
C24 C17 B1 107.4(3) . . ?
C18 C17 H17 108.2 . . ?
C24 C17 H17 108.2 . . ?
B1 C17 H17 108.2 . . ?
C17 C18 C19 115.7(3) . . ?
C17 C18 H18A 108.3 . . ?
C19 C18 H18A 108.3 . . ?
C17 C18 H18B 108.3 . . ?
C19 C18 H18B 108.3 . . ?
H18A C18 H18B 107.4 . . ?
C20 C19 C18 113.9(3) . . ?
C20 C19 H19A 108.8 . . ?
C18 C19 H19A 108.8 . . ?
C20 C19 H19B 108.8 . . ?
C18 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C21 C20 C19 114.9(3) . . ?
C21 C20 H20A 108.5 . . ?
C19 C20 H20A 108.5 . . ?
C21 C20 H20B 108.5 . . ?
C19 C20 H20B 108.5 . . ?
H20A C20 H20B 107.5 . . ?
C20 C21 C22 112.8(3) . . ?
C20 C21 B1 111.6(3) . . ?
C22 C21 B1 107.3(3) . . ?
C20 C21 H21 108.4 . . ?
C22 C21 H21 108.4 . . ?
B1 C21 H21 108.4 . . ?
C23 C22 C21 115.9(3) . . ?
C23 C22 H22A 108.3 . . ?
C21 C22 H22A 108.3 . . ?
C23 C22 H22B 108.3 . . ?
C21 C22 H22B 108.3 . . ?
H22A C22 H22B 107.4 . . ?
C22 C23 C24 116.2(3) . . ?
C22 C23 H23A 108.2 . . ?
C24 C23 H23A 108.2 . . ?
C22 C23 H23B 108.2 . . ?
C24 C23 H23B 108.2 . . ?
H23A C23 H23B 107.4 . . ?
C17 C24 C23 114.5(3) . . ?
C17 C24 H24A 108.6 . . ?
C23 C24 H24A 108.6 . . ?
C17 C24 H24B 108.6 . . ?
C23 C24 H24B 108.6 . . ?
H24A C24 H24B 107.6 . . ?
C16 B1 C17 115.7(3) . . ?
C16 B1 C21 113.1(3) . . ?
C17 B1 C21 105.8(3) . . ?
C16 B1 N4 105.8(3) . . ?
C17 B1 N4 107.1(3) . . ?
C21 B1 N4 109.1(3) . . ?
C2 N1 C6 119.8(3) . . ?
C2 N1 Zn1 127.1(3) . . ?
C6 N1 Zn1 113.0(2) . . ?
C7 N2 N3 107.5(3) . . ?
C7 N2 Zn1 113.5(2) . . ?
N3 N2 Zn1 139.0(2) . . ?
N2 N3 C9 110.6(3) . . ?
N2 N3 C14 116.7(3) . . ?
C9 N3 C14 131.8(3) . . ?
N5 N4 B1 114.6(3) . . ?
N5 N4 H4A 108.6 . . ?
B1 N4 H4A 108.6 . . ?
N5 N4 H4B 108.6 . . ?
B1 N4 H4B 108.6 . . ?
H4A N4 H4B 107.6 . . ?
N4 N5 H5A 108(3) . . ?
N4 N5 H5B 105(4) . . ?
H5A N5 H5B 104(5) . . ?
N2 Zn1 N1 80.21(11) . . ?
N2 Zn1 Br2 114.41(8) . . ?
N1 Zn1 Br2 116.42(7) . . ?
N2 Zn1 Br1 113.42(8) . . ?
N1 Zn1 Br1 110.57(8) . . ?
Br2 Zn1 Br1 116.56(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 -2.1(6) . . . . ?
C1 C2 C3 C4 178.4(4) . . . . ?
C2 C3 C4 C5 2.4(6) . . . . ?
C3 C4 C5 C6 0.0(5) . . . . ?
C4 C5 C6 N1 -3.0(5) . . . . ?
C4 C5 C6 C7 173.2(3) . . . . ?
N1 C6 C7 N2 -3.8(4) . . . . ?
C5 C6 C7 N2 179.8(3) . . . . ?
N1 C6 C7 C8 169.6(3) . . . . ?
C5 C6 C7 C8 -6.9(6) . . . . ?
N2 C7 C8 C9 1.0(4) . . . . ?
C6 C7 C8 C9 -172.8(3) . . . . ?
C7 C8 C9 N3 -1.4(4) . . . . ?
C7 C8 C9 C10 176.3(3) . . . . ?
N3 C9 C10 C11 -172.4(3) . . . . ?
C8 C9 C10 C11 10.3(5) . . . . ?
N3 C9 C10 C12 69.7(4) . . . . ?
C8 C9 C10 C12 -107.6(4) . . . . ?
N3 C9 C10 C13 -53.2(4) . . . . ?
C8 C9 C10 C13 129.5(4) . . . . ?
N3 C14 C15 C16 169.8(3) . . . . ?
C14 C15 C16 B1 -174.6(3) . . . . ?
C24 C17 C18 C19 -69.3(4) . . . . ?
B1 C17 C18 C19 51.9(4) . . . . ?
C17 C18 C19 C20 -43.7(5) . . . . ?
C18 C19 C20 C21 44.7(5) . . . . ?
C19 C20 C21 C22 66.6(4) . . . . ?
C19 C20 C21 B1 -54.2(4) . . . . ?
C20 C21 C22 C23 -71.2(4) . . . . ?
B1 C21 C22 C23 52.0(4) . . . . ?
C21 C22 C23 C24 -39.2(5) . . . . ?
C18 C17 C24 C23 69.0(4) . . . . ?
B1 C17 C24 C23 -54.5(4) . . . . ?
C22 C23 C24 C17 40.2(5) . . . . ?
C15 C16 B1 C17 -59.1(4) . . . . ?
C15 C16 B1 C21 178.7(3) . . . . ?
C15 C16 B1 N4 59.2(4) . . . . ?
C18 C17 B1 C16 176.8(3) . . . . ?
C24 C17 B1 C16 -58.8(4) . . . . ?
C18 C17 B1 C21 -57.1(4) . . . . ?
C24 C17 B1 C21 67.3(4) . . . . ?
C18 C17 B1 N4 59.2(4) . . . . ?
C24 C17 B1 N4 -176.4(3) . . . . ?
C20 C21 B1 C16 -173.9(3) . . . . ?
C22 C21 B1 C16 62.1(4) . . . . ?
C20 C21 B1 C17 58.5(4) . . . . ?
C22 C21 B1 C17 -65.5(4) . . . . ?
C20 C21 B1 N4 -56.5(4) . . . . ?
C22 C21 B1 N4 179.6(3) . . . . ?
C3 C2 N1 C6 -0.8(5) . . . . ?
C1 C2 N1 C6 178.8(3) . . . . ?
C3 C2 N1 Zn1 177.0(3) . . . . ?
C1 C2 N1 Zn1 -3.4(5) . . . . ?
C5 C6 N1 C2 3.4(5) . . . . ?
C7 C6 N1 C2 -173.1(3) . . . . ?
C5 C6 N1 Zn1 -174.7(3) . . . . ?
C7 C6 N1 Zn1 8.8(4) . . . . ?
C8 C7 N2 N3 -0.2(4) . . . . ?
C6 C7 N2 N3 174.6(3) . . . . ?
C8 C7 N2 Zn1 -178.1(2) . . . . ?
C6 C7 N2 Zn1 -3.4(4) . . . . ?
C7 N2 N3 C9 -0.7(4) . . . . ?
Zn1 N2 N3 C9 176.4(3) . . . . ?
C7 N2 N3 C14 -171.5(3) . . . . ?
Zn1 N2 N3 C14 5.7(5) . . . . ?
C8 C9 N3 N2 1.4(4) . . . . ?
C10 C9 N3 N2 -176.4(3) . . . . ?
C8 C9 N3 C14 170.2(3) . . . . ?
C10 C9 N3 C14 -7.6(5) . . . . ?
C15 C14 N3 N2 -72.2(4) . . . . ?
C15 C14 N3 C9 119.5(4) . . . . ?
C16 B1 N4 N5 62.8(3) . . . . ?
C17 B1 N4 N5 -173.2(3) . . . . ?
C21 B1 N4 N5 -59.2(4) . . . . ?

_refine_diff_density_max         0.626
_refine_diff_density_min         -0.800
_refine_diff_density_rms         0.090


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_JK4206_0m
_database_code_depnum_ccdc_archive 'CCDC 1941370'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller '
;Purdue University
United States of America
;
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H39 B Br2 Fe N4'
_chemical_formula_weight         610.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   10.7634(4)
_cell_length_b                   12.2556(5)
_cell_length_c                   21.1268(8)
_cell_angle_alpha                90
_cell_angle_beta                 103.7575(12)
_cell_angle_gamma                90
_cell_volume                     2706.92(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9952
_cell_measurement_theta_min      3.6065
_cell_measurement_theta_max      80.9279

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    8.056
_shelx_estimated_absorpt_T_min   0.270
_shelx_estimated_absorpt_T_max   0.296
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5600
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18937
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         4.202
_diffrn_reflns_theta_max         80.914
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             5568
_reflns_number_gt                5257
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Apex3 v2017.3-0 (Bruker, 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev937 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0439P)²+3.0551P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00119(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5568
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0958
_refine_ls_wR_factor_gt          0.0949
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_restrained_S_all      1.138
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.1119(3) 0.9914(3) -0.06360(15) 0.0357(7) Uani 1 1 d . . . . .
H1A H 0.064551 1.058724 -0.078051 0.053 Uiso 1 1 calc R U . . .
H1B H 0.058749 0.942369 -0.044494 0.053 Uiso 1 1 calc R U . . .
H1C H 0.133831 0.955546 -0.100964 0.053 Uiso 1 1 calc R U . . .
C2 C 0.2323(3) 1.0181(2) -0.01345(13) 0.0231(5) Uani 1 1 d . . . . .
C3 C 0.2733(3) 1.1250(2) 0.00041(13) 0.0266(6) Uani 1 1 d . . . . .
H3 H 0.222615 1.183938 -0.020714 0.032 Uiso 1 1 calc R U . . .
C4 C 0.3868(3) 1.1454(2) 0.04452(14) 0.0261(6) Uani 1 1 d . . . . .
H4 H 0.415852 1.218308 0.053293 0.031 Uiso 1 1 calc R U . . .
C5 C 0.4588(3) 1.0590(2) 0.07623(13) 0.0221(5) Uani 1 1 d . . . . .
H5 H 0.537257 1.071432 0.107226 0.026 Uiso 1 1 calc R U . . .
C6 C 0.4132(2) 0.9541(2) 0.06149(12) 0.0176(5) Uani 1 1 d . . . . .
C7 C 0.4819(2) 0.8567(2) 0.09097(11) 0.0160(5) Uani 1 1 d . . . . .
C8 C 0.5989(2) 0.8418(2) 0.13516(12) 0.0176(5) Uani 1 1 d . . . . .
H8 H 0.655470 0.897064 0.156587 0.021 Uiso 1 1 calc R U . . .
C9 C 0.6164(2) 0.7298(2) 0.14160(12) 0.0169(5) Uani 1 1 d . . . . .
C10 C 0.7313(2) 0.6689(2) 0.18190(13) 0.0212(5) Uani 1 1 d . . . . .
C11 C 0.6945(3) 0.5810(3) 0.22613(15) 0.0305(6) Uani 1 1 d . . . . .
H11A H 0.644931 0.523495 0.199153 0.046 Uiso 1 1 calc R U . . .
H11B H 0.642768 0.614003 0.253482 0.046 Uiso 1 1 calc R U . . .
H11C H 0.772174 0.549398 0.253906 0.046 Uiso 1 1 calc R U . . .
C12 C 0.8178(3) 0.7525(3) 0.22587(16) 0.0320(6) Uani 1 1 d . . . . .
H12A H 0.848465 0.806191 0.198730 0.048 Uiso 1 1 calc R U . . .
H12B H 0.891015 0.714849 0.253754 0.048 Uiso 1 1 calc R U . . .
H12C H 0.768977 0.789797 0.253132 0.048 Uiso 1 1 calc R U . . .
C13 C 0.8067(3) 0.6174(3) 0.13619(15) 0.0285(6) Uani 1 1 d . . . . .
H13A H 0.752187 0.564974 0.107276 0.043 Uiso 1 1 calc R U . . .
H13B H 0.882166 0.579789 0.162100 0.043 Uiso 1 1 calc R U . . .
H13C H 0.833894 0.674709 0.110042 0.043 Uiso 1 1 calc R U . . .
C14 C 0.4718(2) 0.5689(2) 0.08970(12) 0.0184(5) Uani 1 1 d . . . . .
H14A H 0.547447 0.520697 0.102605 0.022 Uiso 1 1 calc R U . . .
H14B H 0.434607 0.558164 0.042551 0.022 Uiso 1 1 calc R U . . .
C15 C 0.3733(2) 0.5366(2) 0.12768(12) 0.0188(5) Uani 1 1 d . . . . .
H15A H 0.410489 0.547896 0.174788 0.023 Uiso 1 1 calc R U . . .
H15B H 0.297658 0.584746 0.114606 0.023 Uiso 1 1 calc R U . . .
C16 C 0.3309(2) 0.4181(2) 0.11614(12) 0.0181(5) Uani 1 1 d . . . . .
H16A H 0.405775 0.370449 0.132879 0.022 Uiso 1 1 calc R U . . .
H16B H 0.302430 0.405674 0.068582 0.022 Uiso 1 1 calc R U . . .
C17 C 0.2266(2) 0.4258(2) 0.22303(13) 0.0201(5) Uani 1 1 d . . . . .
H17 H 0.241022 0.506427 0.223287 0.024 Uiso 1 1 calc R U . . .
C18 C 0.3433(3) 0.3723(2) 0.26910(13) 0.0259(6) Uani 1 1 d . . . . .
H18A H 0.421814 0.398070 0.257085 0.031 Uiso 1 1 calc R U . . .
H18B H 0.347457 0.397114 0.314141 0.031 Uiso 1 1 calc R U . . .
C19 C 0.3422(3) 0.2472(3) 0.26805(14) 0.0271(6) Uani 1 1 d . . . . .
H19A H 0.426910 0.220054 0.292187 0.032 Uiso 1 1 calc R U . . .
H19B H 0.277727 0.220639 0.290907 0.032 Uiso 1 1 calc R U . . .
C20 C 0.3119(3) 0.1998(2) 0.19901(14) 0.0227(5) Uani 1 1 d . . . . .
H20A H 0.298018 0.120275 0.201568 0.027 Uiso 1 1 calc R U . . .
H20B H 0.386933 0.210761 0.180209 0.027 Uiso 1 1 calc R U . . .
C21 C 0.1935(2) 0.2509(2) 0.15282(12) 0.0175(5) Uani 1 1 d . . . . .
H21 H 0.185431 0.220169 0.108185 0.021 Uiso 1 1 calc R U . . .
C22 C 0.0694(3) 0.2255(2) 0.17450(14) 0.0243(6) Uani 1 1 d . . . . .
H22A H -0.004142 0.242395 0.137733 0.029 Uiso 1 1 calc R U . . .
H22B H 0.067157 0.146138 0.182930 0.029 Uiso 1 1 calc R U . . .
C23 C 0.0500(3) 0.2862(2) 0.23523(15) 0.0260(6) Uani 1 1 d . . . . .
H23A H 0.091468 0.243196 0.274185 0.031 Uiso 1 1 calc R U . . .
H23B H -0.042760 0.288140 0.233272 0.031 Uiso 1 1 calc R U . . .
C24 C 0.1016(3) 0.4040(2) 0.24492(13) 0.0244(5) Uani 1 1 d . . . . .
H24A H 0.116360 0.422580 0.291722 0.029 Uiso 1 1 calc R U . . .
H24B H 0.034759 0.453916 0.220627 0.029 Uiso 1 1 calc R U . . .
B1 B 0.2160(3) 0.3812(2) 0.14993(14) 0.0176(5) Uani 1 1 d . . . . .
N1 N 0.3016(2) 0.93367(17) 0.01714(10) 0.0179(4) Uani 1 1 d . . . . .
N2 N 0.42920(19) 0.76004(17) 0.07070(10) 0.0161(4) Uani 1 1 d . . . . .
N3 N 0.51260(19) 0.68311(16) 0.10140(10) 0.0162(4) Uani 1 1 d . . . . .
N4 N 0.0850(2) 0.4345(2) 0.10201(11) 0.0256(5) Uani 1 1 d . . . . .
H4A H 0.097773 0.506819 0.096037 0.039(10) Uiso 1 1 calc R . . . .
H4B H 0.018044 0.426054 0.120957 0.042(10) Uiso 1 1 calc R . . . .
H4C H 0.067539 0.399879 0.062790 0.037(10) Uiso 1 1 calc R . . . .
Fe1 Fe 0.25693(4) 0.76502(3) 0.00230(2) 0.01730(12) Uani 1 1 d . . . . .
Br1 Br 0.06823(3) 0.71839(2) 0.03866(2) 0.02645(10) Uani 1 1 d . . . . .
Br2 Br 0.28828(3) 0.69204(3) -0.09705(2) 0.03369(11) 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 1.502(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 N1 1.348(3) . ?
C2 C3 1.391(4) . ?
C3 C4 1.372(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(4) . ?
C5 H5 0.9500 . ?
C6 N1 1.359(3) . ?
C6 C7 1.463(3) . ?
C7 N2 1.339(3) . ?
C7 C8 1.390(3) . ?
C8 C9 1.388(4) . ?
C8 H8 0.9500 . ?
C9 N3 1.358(3) . ?
C9 C10 1.520(3) . ?
C10 C13 1.537(4) . ?
C10 C11 1.539(4) . ?
C10 C12 1.539(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 N3 1.470(3) . ?
C14 C15 1.526(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.525(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 B1 1.632(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.541(4) . ?
C17 C24 1.546(3) . ?
C17 B1 1.616(4) . ?
C17 H17 1.0000 . ?
C18 C19 1.534(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.531(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.542(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.544(3) . ?
C21 B1 1.618(4) . ?
C21 H21 1.0000 . ?
C22 C23 1.540(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.542(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
B1 N4 1.661(4) . ?
N1 Fe1 2.128(2) . ?
N2 N3 1.356(3) . ?
N2 Fe1 2.063(2) . ?
N4 H4A 0.9100 . ?
N4 H4B 0.9100 . ?
N4 H4C 0.9100 . ?
Fe1 Br2 2.3782(5) . ?
Fe1 Br1 2.4049(5) . ?

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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 120.7(3) . . ?
N1 C2 C1 117.2(2) . . ?
C3 C2 C1 122.1(3) . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.6(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 118.2(3) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
N1 C6 C5 122.3(2) . . ?
N1 C6 C7 114.7(2) . . ?
C5 C6 C7 123.0(2) . . ?
N2 C7 C8 110.3(2) . . ?
N2 C7 C6 116.9(2) . . ?
C8 C7 C6 132.7(2) . . ?
C9 C8 C7 106.0(2) . . ?
C9 C8 H8 127.0 . . ?
C7 C8 H8 127.0 . . ?
N3 C9 C8 106.4(2) . . ?
N3 C9 C10 125.6(2) . . ?
C8 C9 C10 127.8(2) . . ?
C9 C10 C13 109.3(2) . . ?
C9 C10 C11 113.0(2) . . ?
C13 C10 C11 110.2(2) . . ?
C9 C10 C12 107.8(2) . . ?
C13 C10 C12 108.6(2) . . ?
C11 C10 C12 107.8(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C15 112.0(2) . . ?
N3 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
N3 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C16 C15 C14 112.4(2) . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C15 C16 B1 115.0(2) . . ?
C15 C16 H16A 108.5 . . ?
B1 C16 H16A 108.5 . . ?
C15 C16 H16B 108.5 . . ?
B1 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C18 C17 C24 112.0(2) . . ?
C18 C17 B1 108.7(2) . . ?
C24 C17 B1 111.0(2) . . ?
C18 C17 H17 108.3 . . ?
C24 C17 H17 108.3 . . ?
B1 C17 H17 108.3 . . ?
C19 C18 C17 114.5(2) . . ?
C19 C18 H18A 108.6 . . ?
C17 C18 H18A 108.6 . . ?
C19 C18 H18B 108.6 . . ?
C17 C18 H18B 108.6 . . ?
H18A C18 H18B 107.6 . . ?
C20 C19 C18 113.1(2) . . ?
C20 C19 H19A 109.0 . . ?
C18 C19 H19A 109.0 . . ?
C20 C19 H19B 109.0 . . ?
C18 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
C19 C20 C21 113.9(2) . . ?
C19 C20 H20A 108.8 . . ?
C21 C20 H20A 108.8 . . ?
C19 C20 H20B 108.8 . . ?
C21 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C20 C21 C22 111.9(2) . . ?
C20 C21 B1 108.4(2) . . ?
C22 C21 B1 111.0(2) . . ?
C20 C21 H21 108.5 . . ?
C22 C21 H21 108.5 . . ?
B1 C21 H21 108.5 . . ?
C23 C22 C21 116.6(2) . . ?
C23 C22 H22A 108.1 . . ?
C21 C22 H22A 108.1 . . ?
C23 C22 H22B 108.1 . . ?
C21 C22 H22B 108.1 . . ?
H22A C22 H22B 107.3 . . ?
C22 C23 C24 116.6(2) . . ?
C22 C23 H23A 108.1 . . ?
C24 C23 H23A 108.1 . . ?
C22 C23 H23B 108.1 . . ?
C24 C23 H23B 108.1 . . ?
H23A C23 H23B 107.3 . . ?
C23 C24 C17 115.7(2) . . ?
C23 C24 H24A 108.4 . . ?
C17 C24 H24A 108.4 . . ?
C23 C24 H24B 108.4 . . ?
C17 C24 H24B 108.4 . . ?
H24A C24 H24B 107.4 . . ?
C17 B1 C21 105.9(2) . . ?
C17 B1 C16 115.8(2) . . ?
C21 B1 C16 115.2(2) . . ?
C17 B1 N4 107.8(2) . . ?
C21 B1 N4 107.3(2) . . ?
C16 B1 N4 104.2(2) . . ?
C2 N1 C6 119.1(2) . . ?
C2 N1 Fe1 126.51(18) . . ?
C6 N1 Fe1 114.33(16) . . ?
C7 N2 N3 106.3(2) . . ?
C7 N2 Fe1 116.09(16) . . ?
N3 N2 Fe1 137.58(16) . . ?
N2 N3 C9 111.0(2) . . ?
N2 N3 C14 116.39(19) . . ?
C9 N3 C14 132.4(2) . . ?
B1 N4 H4A 109.5 . . ?
B1 N4 H4B 109.5 . . ?
H4A N4 H4B 109.5 . . ?
B1 N4 H4C 109.5 . . ?
H4A N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
N2 Fe1 N1 77.96(8) . . ?
N2 Fe1 Br2 108.33(6) . . ?
N1 Fe1 Br2 114.88(6) . . ?
N2 Fe1 Br1 117.12(6) . . ?
N1 Fe1 Br1 111.23(6) . . ?
Br2 Fe1 Br1 120.03(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 1.5(4) . . . . ?
C1 C2 C3 C4 -177.1(3) . . . . ?
C2 C3 C4 C5 -1.4(4) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C4 C5 C6 N1 0.4(4) . . . . ?
C4 C5 C6 C7 178.9(2) . . . . ?
N1 C6 C7 N2 0.9(3) . . . . ?
C5 C6 C7 N2 -177.7(2) . . . . ?
N1 C6 C7 C8 176.8(2) . . . . ?
C5 C6 C7 C8 -1.8(4) . . . . ?
N2 C7 C8 C9 -0.2(3) . . . . ?
C6 C7 C8 C9 -176.4(2) . . . . ?
C7 C8 C9 N3 0.8(3) . . . . ?
C7 C8 C9 C10 177.3(2) . . . . ?
N3 C9 C10 C13 68.6(3) . . . . ?
C8 C9 C10 C13 -107.2(3) . . . . ?
N3 C9 C10 C11 -54.4(3) . . . . ?
C8 C9 C10 C11 129.7(3) . . . . ?
N3 C9 C10 C12 -173.5(2) . . . . ?
C8 C9 C10 C12 10.6(3) . . . . ?
N3 C14 C15 C16 -179.7(2) . . . . ?
C14 C15 C16 B1 -174.6(2) . . . . ?
C24 C17 C18 C19 67.1(3) . . . . ?
B1 C17 C18 C19 -55.9(3) . . . . ?
C17 C18 C19 C20 48.1(3) . . . . ?
C18 C19 C20 C21 -48.8(3) . . . . ?
C19 C20 C21 C22 -65.3(3) . . . . ?
C19 C20 C21 B1 57.5(3) . . . . ?
C20 C21 C22 C23 73.0(3) . . . . ?
B1 C21 C22 C23 -48.3(3) . . . . ?
C21 C22 C23 C24 34.4(4) . . . . ?
C22 C23 C24 C17 -35.1(4) . . . . ?
C18 C17 C24 C23 -71.7(3) . . . . ?
B1 C17 C24 C23 50.1(3) . . . . ?
C18 C17 B1 C21 62.2(2) . . . . ?
C24 C17 B1 C21 -61.4(3) . . . . ?
C18 C17 B1 C16 -66.9(3) . . . . ?
C24 C17 B1 C16 169.5(2) . . . . ?
C18 C17 B1 N4 176.8(2) . . . . ?
C24 C17 B1 N4 53.2(3) . . . . ?
C20 C21 B1 C17 -63.0(2) . . . . ?
C22 C21 B1 C17 60.3(3) . . . . ?
C20 C21 B1 C16 66.4(3) . . . . ?
C22 C21 B1 C16 -170.2(2) . . . . ?
C20 C21 B1 N4 -178.02(19) . . . . ?
C22 C21 B1 N4 -54.7(3) . . . . ?
C15 C16 B1 C17 -41.6(3) . . . . ?
C15 C16 B1 C21 -166.0(2) . . . . ?
C15 C16 B1 N4 76.7(3) . . . . ?
C3 C2 N1 C6 -0.5(4) . . . . ?
C1 C2 N1 C6 178.1(2) . . . . ?
C3 C2 N1 Fe1 -179.30(18) . . . . ?
C1 C2 N1 Fe1 -0.7(3) . . . . ?
C5 C6 N1 C2 -0.4(3) . . . . ?
C7 C6 N1 C2 -179.0(2) . . . . ?
C5 C6 N1 Fe1 178.53(18) . . . . ?
C7 C6 N1 Fe1 -0.1(3) . . . . ?
C8 C7 N2 N3 -0.5(3) . . . . ?
C6 C7 N2 N3 176.38(19) . . . . ?
C8 C7 N2 Fe1 -178.09(15) . . . . ?
C6 C7 N2 Fe1 -1.3(3) . . . . ?
C7 N2 N3 C9 1.0(3) . . . . ?
Fe1 N2 N3 C9 177.82(18) . . . . ?
C7 N2 N3 C14 176.55(19) . . . . ?
Fe1 N2 N3 C14 -6.6(3) . . . . ?
C8 C9 N3 N2 -1.1(3) . . . . ?
C10 C9 N3 N2 -177.7(2) . . . . ?
C8 C9 N3 C14 -175.7(2) . . . . ?
C10 C9 N3 C14 7.7(4) . . . . ?
C15 C14 N3 N2 -76.1(3) . . . . ?
C15 C14 N3 C9 98.3(3) . . . . ?

_refine_diff_density_max         0.611
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.088


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_EN133_2_0m
_database_code_depnum_ccdc_archive 'CCDC 1941377'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller '
;Purdue University
United States of America
;
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H25 Br2 Fe N3'
_chemical_formula_weight         487.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   12.9565(6)
_cell_length_b                   11.5700(5)
_cell_length_c                   14.3493(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.9302(17)
_cell_angle_gamma                90
_cell_volume                     2087.79(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9921
_cell_measurement_theta_min      4.1306
_cell_measurement_theta_max      80.7207

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    10.281
_shelx_estimated_absorpt_T_min   0.141
_shelx_estimated_absorpt_T_max   0.323
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4646
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_process_details   
;
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.
(2015). J. Appl. Cryst. 48 3-10.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27075
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.130
_diffrn_reflns_theta_max         81.179
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4473
_reflns_number_gt                4163
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Apex3 v2017.3-0 (Bruker, 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev937 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0315P)²+3.2464P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00121(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4473
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0888
_refine_ls_wR_factor_gt          0.0847
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_restrained_S_all      1.153
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.0983(3) 0.5292(3) 0.1513(2) 0.0318(7) Uani 1 1 d . . . . .
H1A H 0.106678 0.489134 0.093446 0.048 Uiso 1 1 calc R U . . .
H1B H 0.130278 0.606301 0.154123 0.048 Uiso 1 1 calc R U . . .
H1C H 0.022517 0.536544 0.149561 0.048 Uiso 1 1 calc R U . . .
C2 C 0.1525(2) 0.4616(2) 0.2382(2) 0.0225(5) Uani 1 1 d . . . . .
C3 C 0.2380(2) 0.5053(2) 0.3076(2) 0.0255(6) Uani 1 1 d . . . . .
H3 H 0.263809 0.580881 0.300530 0.031 Uiso 1 1 calc R U . . .
C4 C 0.2856(2) 0.4392(3) 0.3867(2) 0.0268(6) Uani 1 1 d . . . . .
H4 H 0.344299 0.468654 0.433749 0.032 Uiso 1 1 calc R U . . .
C5 C 0.2463(2) 0.3292(3) 0.3965(2) 0.0256(6) Uani 1 1 d . . . . .
H5 H 0.276875 0.282381 0.450443 0.031 Uiso 1 1 calc R U . . .
C6 C 0.1614(2) 0.2896(2) 0.3255(2) 0.0197(5) Uani 1 1 d . . . . .
C7 C 0.1161(2) 0.1736(2) 0.3268(2) 0.0200(5) Uani 1 1 d . . . . .
C8 C 0.1442(2) 0.0812(2) 0.3898(2) 0.0227(5) Uani 1 1 d . . . . .
H8 H 0.197869 0.080225 0.447996 0.027 Uiso 1 1 calc R U . . .
C9 C 0.0776(2) -0.0096(2) 0.3501(2) 0.0223(5) Uani 1 1 d . . . . .
C10 C 0.0757(2) -0.1315(3) 0.3882(2) 0.0290(6) Uani 1 1 d . . . . .
C11 C -0.0347(3) -0.1657(3) 0.3992(3) 0.0386(8) Uani 1 1 d . . . . .
H11A H -0.084019 -0.169683 0.335701 0.058 Uiso 1 1 calc R U . . .
H11B H -0.059986 -0.107854 0.438440 0.058 Uiso 1 1 calc R U . . .
H11C H -0.030885 -0.241340 0.430507 0.058 Uiso 1 1 calc R U . . .
C12 C 0.1150(3) -0.2181(3) 0.3226(3) 0.0400(8) Uani 1 1 d . . . . .
H12A H 0.067415 -0.215768 0.258197 0.060 Uiso 1 1 calc R U . . .
H12B H 0.115236 -0.296163 0.349090 0.060 Uiso 1 1 calc R U . . .
H12C H 0.187172 -0.197247 0.318872 0.060 Uiso 1 1 calc R U . . .
C13 C 0.1532(3) -0.1373(3) 0.4877(3) 0.0447(9) Uani 1 1 d . . . . .
H13A H 0.225006 -0.117629 0.482034 0.067 Uiso 1 1 calc R U . . .
H13B H 0.153193 -0.215660 0.513642 0.067 Uiso 1 1 calc R U . . .
H13C H 0.130851 -0.082302 0.530980 0.067 Uiso 1 1 calc R U . . .
C14 C -0.0703(2) -0.0242(3) 0.1941(2) 0.0281(6) Uani 1 1 d . . . . .
H14A H -0.065958 -0.108873 0.204366 0.034 Uiso 1 1 calc R U . . .
H14B H -0.058216 -0.008546 0.129736 0.034 Uiso 1 1 calc R U . . .
C15 C -0.1813(2) 0.0162(3) 0.1959(2) 0.0319(7) Uani 1 1 d . . . . .
H15A H -0.190037 0.098328 0.176216 0.038 Uiso 1 1 calc R U . . .
H15B H -0.191148 0.009928 0.261995 0.038 Uiso 1 1 calc R U . . .
C16 C -0.2648(3) -0.0569(3) 0.1280(3) 0.0407(8) Uani 1 1 d . . . . .
H16A H -0.246943 -0.061217 0.064827 0.049 Uiso 1 1 calc R U . . .
H16B H -0.262831 -0.136443 0.153877 0.049 Uiso 1 1 calc R U . . .
C17 C -0.3761(3) -0.0092(4) 0.1144(4) 0.0631(13) Uani 1 1 d . . . . .
H17A H -0.381848 0.063840 0.078943 0.095 Uiso 1 1 calc R U . . .
H17B H -0.391070 0.004307 0.177282 0.095 Uiso 1 1 calc R U . . .
H17C H -0.427426 -0.064804 0.078177 0.095 Uiso 1 1 calc R U . . .
N1 N 0.11561(17) 0.35403(19) 0.24729(16) 0.0195(4) Uani 1 1 d . . . . .
N2 N 0.03713(18) 0.1431(2) 0.25190(17) 0.0211(5) Uani 1 1 d . . . . .
N3 N 0.01414(18) 0.03145(19) 0.26662(17) 0.0215(5) Uani 1 1 d . . . . .
Fe1 Fe -0.00550(3) 0.26753(4) 0.14553(3) 0.02068(12) Uani 1 1 d . . . . .
Br1 Br 0.05342(3) 0.21271(3) 0.00749(2) 0.03235(11) Uani 1 1 d . . . . .
Br2 Br -0.17279(2) 0.35823(3) 0.13008(2) 0.03546(12) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.496(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 N1 1.350(4) . ?
C2 C3 1.394(4) . ?
C3 C4 1.385(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(4) . ?
C5 H5 0.9500 . ?
C6 N1 1.359(3) . ?
C6 C7 1.467(4) . ?
C7 N2 1.341(4) . ?
C7 C8 1.390(4) . ?
C8 C9 1.392(4) . ?
C8 H8 0.9500 . ?
C9 N3 1.364(4) . ?
C9 C10 1.515(4) . ?
C10 C11 1.528(4) . ?
C10 C13 1.537(5) . ?
C10 C12 1.542(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 N3 1.465(4) . ?
C14 C15 1.518(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.526(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.512(6) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
N1 Fe1 2.120(2) . ?
N2 N3 1.354(3) . ?
N2 Fe1 2.074(2) . ?
Fe1 Br2 2.3700(5) . ?
Fe1 Br1 2.3743(5) . ?

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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 120.3(3) . . ?
N1 C2 C1 117.1(3) . . ?
C3 C2 C1 122.5(3) . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.1(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 118.3(3) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
N1 C6 C5 122.6(3) . . ?
N1 C6 C7 114.6(2) . . ?
C5 C6 C7 122.8(3) . . ?
N2 C7 C8 110.4(2) . . ?
N2 C7 C6 117.4(2) . . ?
C8 C7 C6 132.0(3) . . ?
C7 C8 C9 106.0(2) . . ?
C7 C8 H8 127.0 . . ?
C9 C8 H8 127.0 . . ?
N3 C9 C8 106.2(2) . . ?
N3 C9 C10 125.7(3) . . ?
C8 C9 C10 128.1(3) . . ?
C9 C10 C11 112.0(2) . . ?
C9 C10 C13 108.2(3) . . ?
C11 C10 C13 108.1(3) . . ?
C9 C10 C12 110.3(3) . . ?
C11 C10 C12 110.4(3) . . ?
C13 C10 C12 107.5(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C15 113.6(2) . . ?
N3 C14 H14A 108.8 . . ?
C15 C14 H14A 108.8 . . ?
N3 C14 H14B 108.8 . . ?
C15 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 C16 110.3(3) . . ?
C14 C15 H15A 109.6 . . ?
C16 C15 H15A 109.6 . . ?
C14 C15 H15B 109.6 . . ?
C16 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C17 C16 C15 112.8(3) . . ?
C17 C16 H16A 109.0 . . ?
C15 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C15 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C2 N1 C6 119.4(2) . . ?
C2 N1 Fe1 126.11(19) . . ?
C6 N1 Fe1 114.45(17) . . ?
C7 N2 N3 106.3(2) . . ?
C7 N2 Fe1 115.10(18) . . ?
N3 N2 Fe1 138.39(18) . . ?
N2 N3 C9 111.2(2) . . ?
N2 N3 C14 117.6(2) . . ?
C9 N3 C14 131.2(2) . . ?
N2 Fe1 N1 78.40(9) . . ?
N2 Fe1 Br2 116.86(7) . . ?
N1 Fe1 Br2 111.35(6) . . ?
N2 Fe1 Br1 110.27(7) . . ?
N1 Fe1 Br1 111.56(6) . . ?
Br2 Fe1 Br1 120.72(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 -0.4(4) . . . . ?
C1 C2 C3 C4 -179.9(3) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C3 C4 C5 C6 0.8(4) . . . . ?
C4 C5 C6 N1 0.0(4) . . . . ?
C4 C5 C6 C7 177.8(3) . . . . ?
N1 C6 C7 N2 1.0(4) . . . . ?
C5 C6 C7 N2 -177.0(3) . . . . ?
N1 C6 C7 C8 175.7(3) . . . . ?
C5 C6 C7 C8 -2.3(5) . . . . ?
N2 C7 C8 C9 -0.2(3) . . . . ?
C6 C7 C8 C9 -175.3(3) . . . . ?
C7 C8 C9 N3 0.2(3) . . . . ?
C7 C8 C9 C10 178.6(3) . . . . ?
N3 C9 C10 C11 -56.2(4) . . . . ?
C8 C9 C10 C11 125.7(3) . . . . ?
N3 C9 C10 C13 -175.3(3) . . . . ?
C8 C9 C10 C13 6.5(4) . . . . ?
N3 C9 C10 C12 67.3(4) . . . . ?
C8 C9 C10 C12 -110.9(3) . . . . ?
N3 C14 C15 C16 -172.4(3) . . . . ?
C14 C15 C16 C17 -170.8(3) . . . . ?
C3 C2 N1 C6 1.1(4) . . . . ?
C1 C2 N1 C6 -179.3(3) . . . . ?
C3 C2 N1 Fe1 -175.3(2) . . . . ?
C1 C2 N1 Fe1 4.3(4) . . . . ?
C5 C6 N1 C2 -1.0(4) . . . . ?
C7 C6 N1 C2 -179.0(2) . . . . ?
C5 C6 N1 Fe1 175.9(2) . . . . ?
C7 C6 N1 Fe1 -2.1(3) . . . . ?
C8 C7 N2 N3 0.2(3) . . . . ?
C6 C7 N2 N3 176.0(2) . . . . ?
C8 C7 N2 Fe1 -175.12(18) . . . . ?
C6 C7 N2 Fe1 0.7(3) . . . . ?
C7 N2 N3 C9 0.0(3) . . . . ?
Fe1 N2 N3 C9 173.6(2) . . . . ?
C7 N2 N3 C14 -179.8(2) . . . . ?
Fe1 N2 N3 C14 -6.2(4) . . . . ?
C8 C9 N3 N2 -0.1(3) . . . . ?
C10 C9 N3 N2 -178.6(2) . . . . ?
C8 C9 N3 C14 179.6(3) . . . . ?
C10 C9 N3 C14 1.1(5) . . . . ?
C15 C14 N3 N2 -73.4(3) . . . . ?
C15 C14 N3 C9 107.0(3) . . . . ?

_refine_diff_density_max         0.548
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.093


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_EN131_2_0m
_database_code_depnum_ccdc_archive 'CCDC 1941373'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller '
;Purdue University
United States of America
;
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26.50 H42 B Br2 N3 Zn'
_chemical_formula_weight         638.63

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   15.5446(4)
_cell_length_b                   11.6473(3)
_cell_length_c                   16.4931(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.7931(10)
_cell_angle_gamma                90
_cell_volume                     2985.83(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9961
_cell_measurement_theta_min      4.6479
_cell_measurement_theta_max      79.9746

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_F_000             1308
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    4.402
_shelx_estimated_absorpt_T_min   0.362
_shelx_estimated_absorpt_T_max   0.844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4944
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31007
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.648
_diffrn_reflns_theta_max         80.760
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6372
_reflns_number_gt                5815
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Apex3 v2017.3-0 (Bruker, 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev937 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
A pentane molecule is disordered around an inversion center. C-C bond 
distances were restrained to target values (1.55(2) and 1.47(2) Angstrom) 
and bond angles to minimum values(1.3 distances to at least 2.50(2) 
Angstrom). Uij components of ADPs for disordered atoms closer to each other 
than 2.0 Angstrom were restrained to be similar. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0453P)²+3.2153P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6372
_refine_ls_number_parameters     331
_refine_ls_number_restraints     61
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.1008
_refine_ls_wR_factor_gt          0.0988
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.143
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.47032(2) 0.77789(2) 0.02588(2) 0.03071(9) Uani 1 1 d . . . . .
Br2 Br 0.71050(2) 0.63266(3) 0.00831(2) 0.03409(9) Uani 1 1 d . . . . .
Zn1 Zn 0.60276(2) 0.72070(3) 0.08321(2) 0.02291(10) Uani 1 1 d . . . . .
N1 N 0.58667(13) 0.63923(17) 0.19390(11) 0.0214(4) Uani 1 1 d . . . . .
N2 N 0.64426(13) 0.84893(17) 0.15985(12) 0.0212(4) Uani 1 1 d . . . . .
N3 N 0.67158(14) 0.95907(17) 0.15749(12) 0.0226(4) Uani 1 1 d . . . . .
C1 C 0.5372(2) 0.4629(2) 0.13039(16) 0.0320(6) Uani 1 1 d . . . . .
H1A H 0.491024 0.500296 0.099107 0.048 Uiso 1 1 calc R U . . .
H1B H 0.518855 0.385687 0.146121 0.048 Uiso 1 1 calc R U . . .
H1C H 0.588828 0.457603 0.097162 0.048 Uiso 1 1 calc R U . . .
C2 C 0.55685(16) 0.5319(2) 0.20472(15) 0.0236(5) Uani 1 1 d . . . . .
C3 C 0.54573(17) 0.4901(2) 0.28312(15) 0.0260(5) Uani 1 1 d . . . . .
H3 H 0.525733 0.413910 0.291079 0.031 Uiso 1 1 calc R U . . .
C4 C 0.56384(17) 0.5596(2) 0.34948(15) 0.0272(5) Uani 1 1 d . . . . .
H4 H 0.554269 0.532276 0.402873 0.033 Uiso 1 1 calc R U . . .
C5 C 0.59598(17) 0.6692(2) 0.33735(14) 0.0250(5) Uani 1 1 d . . . . .
H5 H 0.609795 0.717664 0.381977 0.030 Uiso 1 1 calc R U . . .
C6 C 0.60741(16) 0.7060(2) 0.25840(14) 0.0218(5) Uani 1 1 d . . . . .
C7 C 0.64055(16) 0.8204(2) 0.23856(14) 0.0217(4) Uani 1 1 d . . . . .
C8 C 0.66661(17) 0.9121(2) 0.28678(14) 0.0248(5) Uani 1 1 d . . . . .
H8 H 0.670318 0.913855 0.344310 0.030 Uiso 1 1 calc R U . . .
C9 C 0.68612(16) 1.0007(2) 0.23395(15) 0.0241(5) Uani 1 1 d . . . . .
C10 C 0.71676(18) 1.1211(2) 0.25414(17) 0.0294(5) Uani 1 1 d . . . . .
C11 C 0.7296(2) 1.1286(3) 0.34654(19) 0.0423(7) Uani 1 1 d . . . . .
H11A H 0.771006 1.070100 0.364365 0.063 Uiso 1 1 calc R U . . .
H11B H 0.674432 1.115563 0.373155 0.063 Uiso 1 1 calc R U . . .
H11C H 0.751399 1.204914 0.361031 0.063 Uiso 1 1 calc R U . . .
C12 C 0.6487(2) 1.2105(2) 0.2295(2) 0.0375(6) Uani 1 1 d . . . . .
H12A H 0.639440 1.208012 0.170642 0.056 Uiso 1 1 calc R U . . .
H12B H 0.668717 1.287211 0.245359 0.056 Uiso 1 1 calc R U . . .
H12C H 0.594604 1.193464 0.256798 0.056 Uiso 1 1 calc R U . . .
C13 C 0.8030(2) 1.1454(3) 0.2141(2) 0.0417(7) Uani 1 1 d . . . . .
H13A H 0.795195 1.145723 0.155006 0.063 Uiso 1 1 calc R U . . .
H13B H 0.844479 1.085721 0.229556 0.063 Uiso 1 1 calc R U . . .
H13C H 0.824528 1.220463 0.231971 0.063 Uiso 1 1 calc R U . . .
C14 C 0.68070(17) 1.0116(2) 0.07719(14) 0.0250(5) Uani 1 1 d . . . . .
H14A H 0.686411 1.095720 0.083695 0.030 Uiso 1 1 calc R U . . .
H14B H 0.627795 0.996645 0.044779 0.030 Uiso 1 1 calc R U . . .
C15 C 0.75774(17) 0.9667(2) 0.03113(15) 0.0278(5) Uani 1 1 d . . . . .
H15A H 0.749533 0.884015 0.019575 0.033 Uiso 1 1 calc R U . . .
H15B H 0.810212 0.975079 0.065322 0.033 Uiso 1 1 calc R U . . .
C16 C 0.76997(17) 1.0312(2) -0.04853(16) 0.0295(5) Uani 1 1 d . . . . .
H16A H 0.781550 1.112644 -0.035030 0.035 Uiso 1 1 calc R U . . .
H16B H 0.714517 1.028979 -0.078742 0.035 Uiso 1 1 calc R U . . .
B1 B 0.8416(2) 0.9905(3) -0.10745(19) 0.0326(6) Uani 1 1 d . . . . .
C17 C 0.9054(2) 0.8889(3) -0.0929(2) 0.0404(7) Uani 1 1 d . . . . .
H17 H 0.902365 0.862133 -0.035454 0.049 Uiso 1 1 calc R U . . .
C18 C 0.8697(3) 0.7943(3) -0.1513(3) 0.0611(10) Uani 1 1 d . . . . .
H18A H 0.907039 0.725710 -0.147205 0.073 Uiso 1 1 calc R U . . .
H18B H 0.811424 0.771887 -0.133594 0.073 Uiso 1 1 calc R U . . .
C19 C 0.8647(3) 0.8331(4) -0.2399(3) 0.0651(11) Uani 1 1 d . . . . .
H19A H 0.923764 0.842083 -0.260580 0.078 Uiso 1 1 calc R U . . .
H19B H 0.835641 0.772757 -0.272460 0.078 Uiso 1 1 calc R U . . .
C20 C 0.8164(3) 0.9456(4) -0.2510(2) 0.0571(10) Uani 1 1 d . . . . .
H20A H 0.754695 0.932581 -0.240125 0.069 Uiso 1 1 calc R U . . .
H20B H 0.821300 0.970593 -0.308102 0.069 Uiso 1 1 calc R U . . .
C21 C 0.8498(2) 1.0424(3) -0.19518(18) 0.0389(7) Uani 1 1 d . . . . .
H21 H 0.811990 1.111415 -0.200837 0.047 Uiso 1 1 calc R U . . .
C22 C 0.9444(2) 1.0756(3) -0.2129(2) 0.0468(8) Uani 1 1 d . . . . .
H22A H 0.962726 1.036038 -0.262891 0.056 Uiso 1 1 calc R U . . .
H22B H 0.947452 1.159320 -0.222904 0.056 Uiso 1 1 calc R U . . .
C23 C 1.0069(2) 1.0449(4) -0.1439(3) 0.0547(9) Uani 1 1 d . . . . .
H23A H 1.066401 1.056245 -0.162989 0.066 Uiso 1 1 calc R U . . .
H23B H 0.997675 1.098660 -0.098394 0.066 Uiso 1 1 calc R U . . .
C24 C 0.9986(2) 0.9247(4) -0.1130(2) 0.0527(9) Uani 1 1 d . . . . .
H24A H 1.034762 0.916613 -0.063410 0.063 Uiso 1 1 calc R U . . .
H24B H 1.021312 0.871297 -0.154152 0.063 Uiso 1 1 calc R U . . .
C25 C 0.8762(13) 1.1482(15) 0.5370(14) 0.166(7) Uani 0.5 1 d D U P A -1
H25A H 0.851801 1.220778 0.517312 0.249 Uiso 0.5 1 calc R U P A -1
H25B H 0.889782 1.154705 0.594986 0.249 Uiso 0.5 1 calc R U P A -1
H25C H 0.834329 1.086306 0.528302 0.249 Uiso 0.5 1 calc R U P A -1
C26 C 0.9592(15) 1.1209(17) 0.4901(17) 0.188(6) Uani 0.5 1 d D U P A -1
H26A H 1.002011 1.183394 0.496367 0.225 Uiso 0.5 1 calc R U P A -1
H26B H 0.946755 1.108858 0.431730 0.225 Uiso 0.5 1 calc R U P A -1
C27 C 0.9915(17) 1.0085(17) 0.5312(14) 0.190(6) Uani 0.5 1 d D U P A -1
H27A H 1.005154 1.025096 0.588821 0.228 Uiso 0.5 1 calc R U P A -1
H27B H 0.944017 0.951785 0.529942 0.228 Uiso 0.5 1 calc R U P A -1
C28 C 1.0633(13) 0.9589(16) 0.4962(18) 0.192(6) Uani 0.5 1 d D U P A -1
H28A H 1.115707 1.000793 0.513872 0.230 Uiso 0.5 1 calc R U P A -1
H28B H 1.058450 0.964620 0.436409 0.230 Uiso 0.5 1 calc R U P A -1
C29 C 1.0710(14) 0.8274(15) 0.5221(17) 0.179(7) Uani 0.5 1 d D U P A -1
H29A H 1.066322 0.778706 0.473787 0.269 Uiso 0.5 1 calc R U P A -1
H29B H 1.024661 0.808302 0.559479 0.269 Uiso 0.5 1 calc R U P A -1
H29C H 1.126757 0.814309 0.549000 0.269 Uiso 0.5 1 calc R U P A -1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Zn1 2.3500(4) . ?
Br2 Zn1 2.3323(4) . ?
Zn1 N2 2.055(2) . ?
Zn1 N1 2.0758(19) . ?
N1 C2 1.346(3) . ?
N1 C6 1.353(3) . ?
N2 C7 1.342(3) . ?
N2 N3 1.352(3) . ?
N3 C9 1.367(3) . ?
N3 C14 1.467(3) . ?
C1 C2 1.494(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.395(3) . ?
C3 C4 1.387(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.467(3) . ?
C7 C8 1.389(3) . ?
C8 C9 1.387(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.515(3) . ?
C10 C13 1.529(4) . ?
C10 C12 1.535(4) . ?
C10 C11 1.537(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.519(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.528(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 B1 1.562(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
B1 C17 1.560(4) . ?
B1 C21 1.575(4) . ?
C17 C24 1.547(5) . ?
C17 C18 1.560(6) . ?
C17 H17 1.0000 . ?
C18 C19 1.530(6) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.520(7) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.541(5) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.552(4) . ?
C21 H21 1.0000 . ?
C22 C23 1.528(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.496(6) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.546(18) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.555(17) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.389(17) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.595(17) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Zn1 N1 80.32(8) . . ?
N2 Zn1 Br2 115.08(6) . . ?
N1 Zn1 Br2 111.16(6) . . ?
N2 Zn1 Br1 107.90(6) . . ?
N1 Zn1 Br1 111.58(6) . . ?
Br2 Zn1 Br1 122.889(16) . . ?
C2 N1 C6 120.5(2) . . ?
C2 N1 Zn1 125.95(16) . . ?
C6 N1 Zn1 113.48(16) . . ?
C7 N2 N3 106.30(19) . . ?
C7 N2 Zn1 113.44(16) . . ?
N3 N2 Zn1 140.17(15) . . ?
N2 N3 C9 111.00(19) . . ?
N2 N3 C14 117.10(19) . . ?
C9 N3 C14 131.9(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 119.6(2) . . ?
N1 C2 C1 117.2(2) . . ?
C3 C2 C1 123.1(2) . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 119.5(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C6 C5 C4 118.2(2) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
N1 C6 C5 121.9(2) . . ?
N1 C6 C7 115.3(2) . . ?
C5 C6 C7 122.8(2) . . ?
N2 C7 C8 110.3(2) . . ?
N2 C7 C6 117.4(2) . . ?
C8 C7 C6 132.2(2) . . ?
C9 C8 C7 106.1(2) . . ?
C9 C8 H8 126.9 . . ?
C7 C8 H8 126.9 . . ?
N3 C9 C8 106.3(2) . . ?
N3 C9 C10 125.3(2) . . ?
C8 C9 C10 128.4(2) . . ?
C9 C10 C13 110.6(2) . . ?
C9 C10 C12 110.9(2) . . ?
C13 C10 C12 111.4(3) . . ?
C9 C10 C11 107.9(2) . . ?
C13 C10 C11 108.4(3) . . ?
C12 C10 C11 107.6(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C15 113.3(2) . . ?
N3 C14 H14A 108.9 . . ?
C15 C14 H14A 108.9 . . ?
N3 C14 H14B 108.9 . . ?
C15 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 C16 111.7(2) . . ?
C14 C15 H15A 109.3 . . ?
C16 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
C16 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 B1 118.9(2) . . ?
C15 C16 H16A 107.6 . . ?
B1 C16 H16A 107.6 . . ?
C15 C16 H16B 107.6 . . ?
B1 C16 H16B 107.6 . . ?
H16A C16 H16B 107.0 . . ?
C17 B1 C16 126.3(2) . . ?
C17 B1 C21 111.9(3) . . ?
C16 B1 C21 121.5(3) . . ?
C24 C17 C18 112.7(3) . . ?
C24 C17 B1 111.0(3) . . ?
C18 C17 B1 102.7(3) . . ?
C24 C17 H17 110.1 . . ?
C18 C17 H17 110.1 . . ?
B1 C17 H17 110.1 . . ?
C19 C18 C17 113.2(3) . . ?
C19 C18 H18A 108.9 . . ?
C17 C18 H18A 108.9 . . ?
C19 C18 H18B 108.9 . . ?
C17 C18 H18B 108.9 . . ?
H18A C18 H18B 107.8 . . ?
C20 C19 C18 112.8(3) . . ?
C20 C19 H19A 109.0 . . ?
C18 C19 H19A 109.0 . . ?
C20 C19 H19B 109.0 . . ?
C18 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
C19 C20 C21 113.4(3) . . ?
C19 C20 H20A 108.9 . . ?
C21 C20 H20A 108.9 . . ?
C19 C20 H20B 108.9 . . ?
C21 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
C20 C21 C22 112.5(3) . . ?
C20 C21 B1 103.7(3) . . ?
C22 C21 B1 111.0(3) . . ?
C20 C21 H21 109.8 . . ?
C22 C21 H21 109.8 . . ?
B1 C21 H21 109.8 . . ?
C23 C22 C21 113.3(3) . . ?
C23 C22 H22A 108.9 . . ?
C21 C22 H22A 108.9 . . ?
C23 C22 H22B 108.9 . . ?
C21 C22 H22B 108.9 . . ?
H22A C22 H22B 107.7 . . ?
C24 C23 C22 114.6(3) . . ?
C24 C23 H23A 108.6 . . ?
C22 C23 H23A 108.6 . . ?
C24 C23 H23B 108.6 . . ?
C22 C23 H23B 108.6 . . ?
H23A C23 H23B 107.6 . . ?
C23 C24 C17 114.2(3) . . ?
C23 C24 H24A 108.7 . . ?
C17 C24 H24A 108.7 . . ?
C23 C24 H24B 108.7 . . ?
C17 C24 H24B 108.7 . . ?
H24A C24 H24B 107.6 . . ?
C26 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C26 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C25 C26 C27 102.8(15) . . ?
C25 C26 H26A 111.2 . . ?
C27 C26 H26A 111.2 . . ?
C25 C26 H26B 111.2 . . ?
C27 C26 H26B 111.2 . . ?
H26A C26 H26B 109.1 . . ?
C28 C27 C26 115.1(16) . . ?
C28 C27 H27A 108.5 . . ?
C26 C27 H27A 108.5 . . ?
C28 C27 H27B 108.5 . . ?
C26 C27 H27B 108.5 . . ?
H27A C27 H27B 107.5 . . ?
C27 C28 C29 110.2(17) . . ?
C27 C28 H28A 109.6 . . ?
C29 C28 H28A 109.6 . . ?
C27 C28 H28B 109.6 . . ?
C29 C28 H28B 109.6 . . ?
H28A C28 H28B 108.1 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N2 N3 C9 0.6(3) . . . . ?
Zn1 N2 N3 C9 176.6(2) . . . . ?
C7 N2 N3 C14 -179.7(2) . . . . ?
Zn1 N2 N3 C14 -3.7(4) . . . . ?
C6 N1 C2 C3 1.2(4) . . . . ?
Zn1 N1 C2 C3 -177.09(18) . . . . ?
C6 N1 C2 C1 -178.7(2) . . . . ?
Zn1 N1 C2 C1 2.9(3) . . . . ?
N1 C2 C3 C4 1.2(4) . . . . ?
C1 C2 C3 C4 -178.9(3) . . . . ?
C2 C3 C4 C5 -2.4(4) . . . . ?
C3 C4 C5 C6 1.1(4) . . . . ?
C2 N1 C6 C5 -2.5(4) . . . . ?
Zn1 N1 C6 C5 176.02(19) . . . . ?
C2 N1 C6 C7 179.0(2) . . . . ?
Zn1 N1 C6 C7 -2.5(3) . . . . ?
C4 C5 C6 N1 1.3(4) . . . . ?
C4 C5 C6 C7 179.7(2) . . . . ?
N3 N2 C7 C8 -0.7(3) . . . . ?
Zn1 N2 C7 C8 -177.93(17) . . . . ?
N3 N2 C7 C6 176.4(2) . . . . ?
Zn1 N2 C7 C6 -0.8(3) . . . . ?
N1 C6 C7 N2 2.2(3) . . . . ?
C5 C6 C7 N2 -176.3(2) . . . . ?
N1 C6 C7 C8 178.6(3) . . . . ?
C5 C6 C7 C8 0.1(4) . . . . ?
N2 C7 C8 C9 0.6(3) . . . . ?
C6 C7 C8 C9 -176.0(3) . . . . ?
N2 N3 C9 C8 -0.2(3) . . . . ?
C14 N3 C9 C8 -179.9(2) . . . . ?
N2 N3 C9 C10 -179.7(2) . . . . ?
C14 N3 C9 C10 0.6(4) . . . . ?
C7 C8 C9 N3 -0.3(3) . . . . ?
C7 C8 C9 C10 179.2(2) . . . . ?
N3 C9 C10 C13 -58.3(4) . . . . ?
C8 C9 C10 C13 122.3(3) . . . . ?
N3 C9 C10 C12 65.7(3) . . . . ?
C8 C9 C10 C12 -113.7(3) . . . . ?
N3 C9 C10 C11 -176.7(3) . . . . ?
C8 C9 C10 C11 3.9(4) . . . . ?
N2 N3 C14 C15 -72.8(3) . . . . ?
C9 N3 C14 C15 106.8(3) . . . . ?
N3 C14 C15 C16 -174.6(2) . . . . ?
C14 C15 C16 B1 -175.1(2) . . . . ?
C15 C16 B1 C17 -1.1(5) . . . . ?
C15 C16 B1 C21 171.9(3) . . . . ?
C16 B1 C17 C24 -133.3(3) . . . . ?
C21 B1 C17 C24 53.1(4) . . . . ?
C16 B1 C17 C18 106.0(3) . . . . ?
C21 B1 C17 C18 -67.6(3) . . . . ?
C24 C17 C18 C19 -61.9(4) . . . . ?
B1 C17 C18 C19 57.6(4) . . . . ?
C17 C18 C19 C20 -52.5(5) . . . . ?
C18 C19 C20 C21 52.0(4) . . . . ?
C19 C20 C21 C22 63.3(4) . . . . ?
C19 C20 C21 B1 -56.7(4) . . . . ?
C17 B1 C21 C20 67.7(3) . . . . ?
C16 B1 C21 C20 -106.3(3) . . . . ?
C17 B1 C21 C22 -53.4(4) . . . . ?
C16 B1 C21 C22 132.7(3) . . . . ?
C20 C21 C22 C23 -112.7(4) . . . . ?
B1 C21 C22 C23 3.0(4) . . . . ?
C21 C22 C23 C24 48.9(5) . . . . ?
C22 C23 C24 C17 -49.7(5) . . . . ?
C18 C17 C24 C23 112.6(4) . . . . ?
B1 C17 C24 C23 -2.0(5) . . . . ?
C25 C26 C27 C28 175(2) . . . . ?
C26 C27 C28 C29 -161(2) . . . . ?

_refine_diff_density_max         0.932
_refine_diff_density_min         -0.563
_refine_diff_density_rms         0.086


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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 
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data_JK5101_0m
_database_code_depnum_ccdc_archive 'CCDC 1941376'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller '
;Purdue University
United States of America
;
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C48 H76 B2 Br4 N8 O Zn2, 3(C2 H4 Cl2)'
_chemical_formula_sum            'C54 H88 B2 Br4 Cl6 N8 O Zn2'
_chemical_formula_weight         1550.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   12.6626(10)
_cell_length_b                   25.463(3)
_cell_length_c                   21.457(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.524(4)
_cell_angle_gamma                90
_cell_volume                     6753.6(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9744
_cell_measurement_theta_min      2.5195
_cell_measurement_theta_max      28.2446

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_F_000             3152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    3.356
_shelx_estimated_absorpt_T_min   0.333
_shelx_estimated_absorpt_T_max   0.906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5857
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            71747
_diffrn_reflns_av_unetI/netI     0.0780
_diffrn_reflns_av_R_equivalents  0.0977
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.235
_diffrn_reflns_theta_max         28.394
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             15991
_reflns_number_gt                9963
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Apex3 v2018.1-0 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev946 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Three dichloroethane molecules were refined as disordered. Two over two 
positions, one over three positions. All disordered moieties were 
restrained to have similar geometries. Uij components of ADPs for 
disordered atoms closer to each other than 2.0 Angstrom were restrained 
to be similar. Subject to these conditions the occupancy rates refined 
to 0.751(6) and 0.249(6) for the molecule involving Cl1 and Cl2; to 
0.485(3), 0.339(3) and 0.177(3) for the molecule involving Cl3 and Cl4;  
and to 0.552(13) and 0.448(13) for the molecule involving Cl5 and Cl6.  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0851P)²+15.1843P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         15991
_refine_ls_number_parameters     851
_refine_ls_number_restraints     526
_refine_ls_R_factor_all          0.1150
_refine_ls_R_factor_gt           0.0652
_refine_ls_wR_factor_ref         0.1862
_refine_ls_wR_factor_gt          0.1576
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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 0.55665(4) -0.04083(2) 0.42676(3) 0.03809(15) Uani 1 1 d . . . . .
Br2 Br 0.74631(5) 0.04359(2) 0.34322(3) 0.04139(15) Uani 1 1 d . . . . .
Br3 Br 1.14294(5) 0.26948(3) 0.26316(4) 0.0602(2) Uani 1 1 d . . . . .
Br4 Br 0.91486(5) 0.17139(3) 0.28981(4) 0.0575(2) Uani 1 1 d . . . . .
Zn1 Zn 0.72710(5) -0.00182(2) 0.43511(3) 0.02849(14) Uani 1 1 d . . . . .
Zn2 Zn 1.09810(5) 0.19672(2) 0.31694(3) 0.03438(16) Uani 1 1 d . . . . .
Cl1 Cl 1.0317(3) 0.49293(13) 0.28930(19) 0.0790(10) Uani 0.751(6) 1 d D U P A 1
C49 C 0.9481(16) 0.4384(6) 0.2594(7) 0.107(3) Uani 0.751(6) 1 d D U P A 1
H49A H 0.871735 0.450082 0.248511 0.128 Uiso 0.751(6) 1 calc R U P A 1
H49B H 0.967478 0.425749 0.219735 0.128 Uiso 0.751(6) 1 calc R U P A 1
C50 C 0.9576(12) 0.3991(5) 0.3009(7) 0.102(3) Uani 0.751(6) 1 d D U P A 1
H50A H 0.946315 0.412190 0.342382 0.123 Uiso 0.751(6) 1 calc R U P A 1
H50B H 1.031348 0.384011 0.307775 0.123 Uiso 0.751(6) 1 calc R U P A 1
Cl2 Cl 0.8575(3) 0.34824(13) 0.27030(13) 0.0741(11) Uani 0.751(6) 1 d D U P A 1
Cl1B Cl 1.0227(19) 0.4761(8) 0.3185(11) 0.159(5) Uani 0.249(6) 1 d D U P A 2
C49B C 0.960(4) 0.4396(16) 0.2496(14) 0.106(4) Uani 0.249(6) 1 d D U P A 2
H49C H 0.890586 0.456735 0.230181 0.127 Uiso 0.249(6) 1 calc R U P A 2
H49D H 1.006868 0.441586 0.218167 0.127 Uiso 0.249(6) 1 calc R U P A 2
C50B C 0.941(2) 0.3891(13) 0.260(2) 0.104(4) Uani 0.249(6) 1 d D U P A 2
H50C H 0.998967 0.374176 0.293610 0.124 Uiso 0.249(6) 1 calc R U P A 2
H50D H 0.935964 0.368271 0.220199 0.124 Uiso 0.249(6) 1 calc R U P A 2
Cl2B Cl 0.8090(10) 0.3893(6) 0.2850(6) 0.107(4) Uani 0.249(6) 1 d D U P A 2
Cl3 Cl 0.3339(8) 0.3631(3) 0.3917(4) 0.123(2) Uani 0.485(3) 1 d D U P B 1
C51 C 0.286(2) 0.4207(8) 0.4248(14) 0.145(4) Uani 0.485(3) 1 d D U P B 1
H51A H 0.239824 0.441302 0.389996 0.174 Uiso 0.485(3) 1 calc R U P B 1
H51B H 0.240218 0.410078 0.454794 0.174 Uiso 0.485(3) 1 calc R U P B 1
C52 C 0.368(3) 0.4515(10) 0.4560(10) 0.147(4) Uani 0.485(3) 1 d D U P B 1
H52A H 0.424670 0.429769 0.483033 0.176 Uiso 0.485(3) 1 calc R U P B 1
H52B H 0.340876 0.477176 0.483507 0.176 Uiso 0.485(3) 1 calc R U P B 1
Cl4 Cl 0.4221(7) 0.4858(3) 0.3933(4) 0.112(2) Uani 0.485(3) 1 d D U P B 1
Cl3B Cl 0.2613(9) 0.3842(4) 0.3810(5) 0.103(3) Uani 0.339(3) 1 d D U P C 2
C51B C 0.269(3) 0.4525(8) 0.4010(19) 0.145(4) Uani 0.339(3) 1 d D U P C 2
H51C H 0.287217 0.472146 0.364969 0.174 Uiso 0.339(3) 1 calc R U P C 2
H51D H 0.196435 0.464222 0.405389 0.174 Uiso 0.339(3) 1 calc R U P C 2
C52B C 0.340(3) 0.4653(14) 0.4540(15) 0.145(4) Uani 0.339(3) 1 d D U P C 2
H52C H 0.373982 0.433225 0.475555 0.174 Uiso 0.339(3) 1 calc R U P C 2
H52D H 0.303103 0.484062 0.483606 0.174 Uiso 0.339(3) 1 calc R U P C 2
Cl4B Cl 0.4446(15) 0.5081(7) 0.4319(9) 0.183(5) Uani 0.339(3) 1 d D U P C 2
Cl3C Cl 0.215(2) 0.4256(9) 0.4566(13) 0.155(5) Uani 0.177(3) 1 d D U P D 3
C51C C 0.350(3) 0.405(2) 0.457(3) 0.143(4) Uani 0.177(3) 1 d D U P D 3
H51E H 0.398319 0.416377 0.497216 0.171 Uiso 0.177(3) 1 calc R U P D 3
H51F H 0.351853 0.365885 0.456079 0.171 Uiso 0.177(3) 1 calc R U P D 3
C52C C 0.390(5) 0.4230(14) 0.408(3) 0.141(4) Uani 0.177(3) 1 d D U P D 3
H52E H 0.357621 0.403761 0.368053 0.169 Uiso 0.177(3) 1 calc R U P D 3
H52F H 0.469176 0.419045 0.416503 0.169 Uiso 0.177(3) 1 calc R U P D 3
Cl4C Cl 0.351(3) 0.4933(10) 0.4002(16) 0.160(5) Uani 0.177(3) 1 d D U P D 3
Cl5 Cl 0.8168(7) 0.6048(3) 0.3948(6) 0.117(3) Uani 0.552(13) 1 d D U P E 1
C53 C 0.720(2) 0.5695(9) 0.3405(13) 0.158(5) Uani 0.552(13) 1 d D U P E 1
H53A H 0.647474 0.577283 0.349165 0.189 Uiso 0.552(13) 1 calc R U P E 1
H53B H 0.719545 0.582201 0.296918 0.189 Uiso 0.552(13) 1 calc R U P E 1
C54 C 0.7331(18) 0.5181(9) 0.3417(15) 0.155(5) Uani 0.552(13) 1 d D U P E 1
H54A H 0.747464 0.504361 0.385921 0.186 Uiso 0.552(13) 1 calc R U P E 1
H54B H 0.792852 0.507690 0.321270 0.186 Uiso 0.552(13) 1 calc R U P E 1
Cl6 Cl 0.5996(10) 0.4951(6) 0.2946(6) 0.168(4) Uani 0.552(13) 1 d D U P E 1
Cl5B Cl 0.7926(16) 0.5923(7) 0.4114(10) 0.186(6) Uani 0.448(13) 1 d D U P E 2
C53B C 0.689(3) 0.5479(14) 0.3763(15) 0.162(5) Uani 0.448(13) 1 d D U P E 2
H53C H 0.699715 0.514579 0.400611 0.195 Uiso 0.448(13) 1 calc R U P E 2
H53D H 0.618543 0.562679 0.379985 0.195 Uiso 0.448(13) 1 calc R U P E 2
C54B C 0.686(3) 0.5377(8) 0.3158(13) 0.153(5) Uani 0.448(13) 1 d D U P E 2
H54C H 0.757283 0.546233 0.305801 0.184 Uiso 0.448(13) 1 calc R U P E 2
H54D H 0.630501 0.559640 0.288325 0.184 Uiso 0.448(13) 1 calc R U P E 2
Cl6B Cl 0.6551(11) 0.4669(4) 0.2995(4) 0.120(4) Uani 0.448(13) 1 d D U P E 2
O1 O 0.7551(3) 0.23996(14) 0.41901(19) 0.0362(9) Uani 1 1 d . . . . .
N1 N 0.8561(3) -0.05167(16) 0.4714(2) 0.0303(9) Uani 1 1 d . . . . .
N2 N 0.7823(3) 0.03125(15) 0.5229(2) 0.0271(9) Uani 1 1 d . . . . .
N3 N 0.7574(3) 0.07095(15) 0.5591(2) 0.0286(9) Uani 1 1 d . . . . .
N4 N 0.6788(4) 0.17512(18) 0.3362(2) 0.0338(10) Uani 1 1 d . . . . .
H4A H 0.743118 0.186482 0.328738 0.041 Uiso 1 1 calc R U . . .
H4B H 0.691444 0.143090 0.355137 0.041 Uiso 1 1 calc R U . . .
N5 N 1.1888(3) 0.12811(17) 0.3163(2) 0.0322(10) Uani 1 1 d . . . . .
N6 N 1.1808(3) 0.19563(16) 0.4099(2) 0.0290(9) Uani 1 1 d . . . . .
N7 N 1.2028(3) 0.22810(17) 0.4604(2) 0.0319(10) Uani 1 1 d . . . . .
N8 N 0.7653(4) 0.29500(18) 0.4126(2) 0.0396(11) Uani 1 1 d . . . . .
H8A H 0.698013 0.309300 0.406494 0.048 Uiso 1 1 calc R U . . .
H8B H 0.790168 0.301089 0.376492 0.048 Uiso 1 1 calc R U . . .
C1 C 0.8339(5) -0.1015(2) 0.3739(3) 0.0475(15) Uani 1 1 d . . . . .
H1A H 0.757427 -0.109950 0.370854 0.071 Uiso 1 1 calc R U . . .
H1B H 0.868837 -0.130291 0.355776 0.071 Uiso 1 1 calc R U . . .
H1C H 0.839525 -0.069094 0.350132 0.071 Uiso 1 1 calc R U . . .
C2 C 0.8878(4) -0.0941(2) 0.4415(3) 0.0352(12) Uani 1 1 d . . . . .
C3 C 0.9666(4) -0.1276(2) 0.4745(3) 0.0407(14) Uani 1 1 d . . . . .
H3 H 0.988892 -0.157033 0.453330 0.049 Uiso 1 1 calc R U . . .
C4 C 1.0124(4) -0.1187(2) 0.5373(3) 0.0392(13) Uani 1 1 d . . . . .
H4 H 1.064311 -0.142651 0.560037 0.047 Uiso 1 1 calc R U . . .
C5 C 0.9832(4) -0.0743(2) 0.5684(3) 0.0347(12) Uani 1 1 d . . . . .
H5 H 1.016347 -0.066538 0.611541 0.042 Uiso 1 1 calc R U . . .
C6 C 0.9034(4) -0.04212(19) 0.5331(3) 0.0284(11) Uani 1 1 d . . . . .
C7 C 0.8632(4) 0.00511(19) 0.5601(3) 0.0292(11) Uani 1 1 d . . . . .
C8 C 0.8913(4) 0.0286(2) 0.6196(3) 0.0325(11) Uani 1 1 d . . . . .
H8 H 0.946992 0.017959 0.654471 0.039 Uiso 1 1 calc R U . . .
C9 C 0.8219(4) 0.0707(2) 0.6181(3) 0.0311(11) Uani 1 1 d . . . . .
C10 C 0.8133(5) 0.1088(2) 0.6716(3) 0.0383(13) Uani 1 1 d . . . . .
C11 C 0.8274(6) 0.1662(2) 0.6515(3) 0.0445(14) Uani 1 1 d . . . . .
H11A H 0.828462 0.189507 0.687984 0.067 Uiso 1 1 calc R U . . .
H11B H 0.766979 0.175844 0.616512 0.067 Uiso 1 1 calc R U . . .
H11C H 0.895582 0.169612 0.637326 0.067 Uiso 1 1 calc R U . . .
C12 C 0.9038(6) 0.0957(3) 0.7292(3) 0.0533(17) Uani 1 1 d . . . . .
H12A H 0.898537 0.118862 0.764882 0.080 Uiso 1 1 calc R U . . .
H12B H 0.974140 0.100696 0.717979 0.080 Uiso 1 1 calc R U . . .
H12C H 0.896813 0.059049 0.741780 0.080 Uiso 1 1 calc R U . . .
C13 C 0.7060(5) 0.1024(2) 0.6917(3) 0.0453(15) Uani 1 1 d . . . . .
H13A H 0.699608 0.066339 0.706494 0.068 Uiso 1 1 calc R U . . .
H13B H 0.646377 0.109735 0.655294 0.068 Uiso 1 1 calc R U . . .
H13C H 0.702837 0.126974 0.726444 0.068 Uiso 1 1 calc R U . . .
C14 C 0.6717(4) 0.1072(2) 0.5268(3) 0.0309(11) Uani 1 1 d . . . . .
H14A H 0.644499 0.127537 0.559471 0.037 Uiso 1 1 calc R U . . .
H14B H 0.610573 0.086519 0.502119 0.037 Uiso 1 1 calc R U . . .
C15 C 0.7111(4) 0.14510(19) 0.4822(3) 0.0297(11) Uani 1 1 d . . . . .
H15A H 0.745656 0.125195 0.452391 0.036 Uiso 1 1 calc R U . . .
H15B H 0.765950 0.168982 0.507375 0.036 Uiso 1 1 calc R U . . .
C16 C 0.6164(4) 0.1774(2) 0.4443(3) 0.0346(12) Uani 1 1 d . . . . .
H16A H 0.587171 0.199574 0.474482 0.041 Uiso 1 1 calc R U . . .
H16B H 0.558395 0.152982 0.423788 0.041 Uiso 1 1 calc R U . . .
C17 C 0.5521(4) 0.2558(2) 0.3580(3) 0.0361(12) Uani 1 1 d . . . . .
H17 H 0.549087 0.282130 0.392102 0.043 Uiso 1 1 calc R U . . .
C18 C 0.5689(5) 0.2887(2) 0.2989(3) 0.0437(14) Uani 1 1 d . . . . .
H18A H 0.497090 0.294576 0.270500 0.052 Uiso 1 1 calc R U . . .
H18B H 0.597785 0.323571 0.314539 0.052 Uiso 1 1 calc R U . . .
C19 C 0.6432(5) 0.2657(2) 0.2589(3) 0.0462(15) Uani 1 1 d . . . . .
H19A H 0.647918 0.291448 0.225032 0.055 Uiso 1 1 calc R U . . .
H19B H 0.716369 0.262790 0.286654 0.055 Uiso 1 1 calc R U . . .
C20 C 0.6149(5) 0.2130(3) 0.2272(3) 0.0485(16) Uani 1 1 d . . . . .
H20A H 0.670649 0.204108 0.202852 0.058 Uiso 1 1 calc R U . . .
H20B H 0.545090 0.216433 0.196026 0.058 Uiso 1 1 calc R U . . .
C21 C 0.6059(5) 0.1664(2) 0.2727(3) 0.0396(13) Uani 1 1 d . . . . .
H21 H 0.635722 0.135101 0.254136 0.047 Uiso 1 1 calc R U . . .
C22 C 0.4911(5) 0.1512(3) 0.2771(3) 0.0462(15) Uani 1 1 d . . . . .
H22A H 0.495605 0.128325 0.314846 0.055 Uiso 1 1 calc R U . . .
H22B H 0.458934 0.130153 0.238905 0.055 Uiso 1 1 calc R U . . .
C23 C 0.4135(5) 0.1969(3) 0.2821(3) 0.0525(17) Uani 1 1 d . . . . .
H23A H 0.411663 0.220472 0.245168 0.063 Uiso 1 1 calc R U . . .
H23B H 0.339963 0.182089 0.277661 0.063 Uiso 1 1 calc R U . . .
C24 C 0.4380(4) 0.2298(3) 0.3419(3) 0.0458(15) Uani 1 1 d . . . . .
H24A H 0.430411 0.207357 0.378340 0.055 Uiso 1 1 calc R U . . .
H24B H 0.382877 0.257870 0.337765 0.055 Uiso 1 1 calc R U . . .
C25 C 1.1202(6) 0.1129(3) 0.2029(3) 0.0560(17) Uani 1 1 d . . . . .
H25A H 1.046344 0.118831 0.208392 0.084 Uiso 1 1 calc R U . . .
H25B H 1.119876 0.084852 0.171516 0.084 Uiso 1 1 calc R U . . .
H25C H 1.148178 0.145261 0.187700 0.084 Uiso 1 1 calc R U . . .
C26 C 1.1915(5) 0.0970(2) 0.2660(3) 0.0400(13) Uani 1 1 d . . . . .
C27 C 1.2589(5) 0.0543(2) 0.2714(3) 0.0450(14) Uani 1 1 d . . . . .
H27 H 1.260265 0.032824 0.235330 0.054 Uiso 1 1 calc R U . . .
C28 C 1.3246(5) 0.0429(2) 0.3300(3) 0.0407(13) Uani 1 1 d . . . . .
H28 H 1.371379 0.013341 0.334378 0.049 Uiso 1 1 calc R U . . .
C29 C 1.3228(4) 0.0739(2) 0.3820(3) 0.0345(12) Uani 1 1 d . . . . .
H29 H 1.367696 0.066334 0.422513 0.041 Uiso 1 1 calc R U . . .
C30 C 1.2528(4) 0.1171(2) 0.3735(3) 0.0308(11) Uani 1 1 d . . . . .
C31 C 1.2512(4) 0.15496(19) 0.4242(3) 0.0282(10) Uani 1 1 d . . . . .
C32 C 1.3175(4) 0.1623(2) 0.4836(3) 0.0319(11) Uani 1 1 d . . . . .
H32 H 1.373332 0.139571 0.504780 0.038 Uiso 1 1 calc R U . . .
C33 C 1.2866(4) 0.2096(2) 0.5063(3) 0.0337(12) Uani 1 1 d . . . . .
C34 C 1.3411(5) 0.2379(2) 0.5670(3) 0.0401(13) Uani 1 1 d . . . . .
C35 C 1.4284(6) 0.2012(3) 0.6052(3) 0.0589(19) Uani 1 1 d . . . . .
H35A H 1.458890 0.216836 0.646944 0.088 Uiso 1 1 calc R U . . .
H35B H 1.485909 0.196146 0.581715 0.088 Uiso 1 1 calc R U . . .
H35C H 1.395838 0.167131 0.611232 0.088 Uiso 1 1 calc R U . . .
C36 C 1.2594(6) 0.2509(3) 0.6085(3) 0.0562(17) Uani 1 1 d . . . . .
H36A H 1.221502 0.218836 0.616282 0.084 Uiso 1 1 calc R U . . .
H36B H 1.206824 0.276631 0.586346 0.084 Uiso 1 1 calc R U . . .
H36C H 1.297859 0.265624 0.649394 0.084 Uiso 1 1 calc R U . . .
C37 C 1.3972(5) 0.2879(3) 0.5508(4) 0.0548(17) Uani 1 1 d . . . . .
H37A H 1.437026 0.304243 0.590234 0.082 Uiso 1 1 calc R U . . .
H37B H 1.342705 0.312478 0.528017 0.082 Uiso 1 1 calc R U . . .
H37C H 1.447567 0.278803 0.523652 0.082 Uiso 1 1 calc R U . . .
C38 C 1.1379(5) 0.2767(2) 0.4556(3) 0.0392(13) Uani 1 1 d . . . . .
H38A H 1.132649 0.292034 0.412693 0.047 Uiso 1 1 calc R U . . .
H38B H 1.176569 0.302247 0.487263 0.047 Uiso 1 1 calc R U . . .
C39 C 1.0241(4) 0.2694(2) 0.4666(3) 0.0374(12) Uani 1 1 d . . . . .
H39A H 1.027555 0.255105 0.509931 0.045 Uiso 1 1 calc R U . . .
H39B H 0.983627 0.244293 0.435110 0.045 Uiso 1 1 calc R U . . .
C40 C 0.9665(4) 0.3224(2) 0.4598(3) 0.0374(12) Uani 1 1 d . . . . .
H40A H 0.964527 0.335324 0.416002 0.045 Uiso 1 1 calc R U . . .
H40B H 1.012301 0.347134 0.489519 0.045 Uiso 1 1 calc R U . . .
C41 C 0.8215(5) 0.3069(2) 0.5380(3) 0.0469(15) Uani 1 1 d . . . . .
H41 H 0.845454 0.269515 0.544134 0.056 Uiso 1 1 calc R U . . .
C42 C 0.6998(6) 0.3095(3) 0.5396(4) 0.0573(18) Uani 1 1 d . . . . .
H42A H 0.660077 0.283220 0.509410 0.069 Uiso 1 1 calc R U . . .
H42B H 0.691251 0.299835 0.582968 0.069 Uiso 1 1 calc R U . . .
C43 C 0.6488(6) 0.3636(3) 0.5225(4) 0.0603(19) Uani 1 1 d . . . . .
H43A H 0.670161 0.386706 0.560223 0.072 Uiso 1 1 calc R U . . .
H43B H 0.569151 0.359607 0.514015 0.072 Uiso 1 1 calc R U . . .
C44 C 0.6781(6) 0.3912(3) 0.4650(4) 0.0589(18) Uani 1 1 d . . . . .
H44A H 0.634403 0.375758 0.425392 0.071 Uiso 1 1 calc R U . . .
H44B H 0.657981 0.428765 0.465884 0.071 Uiso 1 1 calc R U . . .
C45 C 0.7978(5) 0.3875(2) 0.4627(3) 0.0457(14) Uani 1 1 d . . . . .
H45 H 0.806578 0.400760 0.420214 0.055 Uiso 1 1 calc R U . . .
C46 C 0.8698(6) 0.4213(3) 0.5154(4) 0.064(2) Uani 1 1 d . . . . .
H46A H 0.839793 0.457312 0.513329 0.077 Uiso 1 1 calc R U . . .
H46B H 0.943229 0.423598 0.506632 0.077 Uiso 1 1 calc R U . . .
C47 C 0.8789(8) 0.3996(3) 0.5841(4) 0.079(3) Uani 1 1 d . . . . .
H47A H 0.941562 0.416458 0.612696 0.095 Uiso 1 1 calc R U . . .
H47B H 0.813162 0.409803 0.599021 0.095 Uiso 1 1 calc R U . . .
C48 C 0.8924(6) 0.3398(3) 0.5902(4) 0.0600(18) Uani 1 1 d . . . . .
H48A H 0.968949 0.331118 0.591256 0.072 Uiso 1 1 calc R U . . .
H48B H 0.877230 0.329011 0.631758 0.072 Uiso 1 1 calc R U . . .
B1 B 0.6470(5) 0.2150(2) 0.3895(3) 0.0314(13) Uani 1 1 d . . . . .
B2 B 0.8444(5) 0.3268(2) 0.4718(3) 0.0367(14) 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 Zn1 2.3472(8) . ?
Br2 Zn1 2.3436(8) . ?
Br3 Zn2 2.3175(9) . ?
Br4 Zn2 2.3564(9) . ?
Zn1 N2 2.044(4) . ?
Zn1 N1 2.082(4) . ?
Zn2 N6 2.042(4) . ?
Zn2 N5 2.093(4) . ?
Cl1 C49 1.778(11) . ?
C49 C50 1.329(14) . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C50 Cl2 1.831(11) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
Cl1B C49B 1.779(17) . ?
C49B C50B 1.337(18) . ?
C49B H49C 0.9900 . ?
C49B H49D 0.9900 . ?
C50B Cl2B 1.866(17) . ?
C50B H50C 0.9900 . ?
C50B H50D 0.9900 . ?
Cl3 C51 1.795(17) . ?
C51 C52 1.356(18) . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
C52 Cl4 1.857(16) . ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?
Cl3B C51B 1.788(17) . ?
C51B C52B 1.328(19) . ?
C51B H51C 0.9900 . ?
C51B H51D 0.9900 . ?
C52B Cl4B 1.855(17) . ?
C52B H52C 0.9900 . ?
C52B H52D 0.9900 . ?
Cl3C C51C 1.792(18) . ?
C51C C52C 1.342(19) . ?
C51C H51E 0.9900 . ?
C51C H51F 0.9900 . ?
C52C Cl4C 1.854(18) . ?
C52C H52E 0.9900 . ?
C52C H52F 0.9900 . ?
Cl5 C53 1.750(15) . ?
C53 C54 1.319(18) . ?
C53 H53A 0.9900 . ?
C53 H53B 0.9900 . ?
C54 Cl6 1.866(15) . ?
C54 H54A 0.9900 . ?
C54 H54B 0.9900 . ?
Cl5B C53B 1.769(16) . ?
C53B C54B 1.317(18) . ?
C53B H53C 0.9900 . ?
C53B H53D 0.9900 . ?
C54B Cl6B 1.863(16) . ?
C54B H54C 0.9900 . ?
C54B H54D 0.9900 . ?
O1 N8 1.417(6) . ?
O1 B1 1.517(7) . ?
N1 C6 1.352(7) . ?
N1 C2 1.360(7) . ?
N2 C7 1.332(6) . ?
N2 N3 1.353(6) . ?
N3 C9 1.348(7) . ?
N3 C14 1.479(6) . ?
N4 C21 1.487(7) . ?
N4 B1 1.644(8) . ?
N4 H4A 0.9100 . ?
N4 H4B 0.9100 . ?
N5 C30 1.344(7) . ?
N5 C26 1.346(7) . ?
N6 N7 1.343(6) . ?
N6 C31 1.358(6) . ?
N7 C33 1.365(7) . ?
N7 C38 1.477(6) . ?
N8 B2 1.649(8) . ?
N8 H8A 0.9100 . ?
N8 H8B 0.9100 . ?
C1 C2 1.475(9) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.387(8) . ?
C3 C4 1.366(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.403(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.472(7) . ?
C7 C8 1.385(7) . ?
C8 C9 1.380(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.525(8) . ?
C10 C13 1.522(8) . ?
C10 C12 1.530(9) . ?
C10 C11 1.544(8) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.517(7) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.534(7) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 B1 1.628(8) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C24 1.558(8) . ?
C17 C18 1.572(8) . ?
C17 B1 1.621(8) . ?
C17 H17 1.0000 . ?
C18 C19 1.521(9) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.513(9) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.558(8) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.526(8) . ?
C21 H21 1.0000 . ?
C22 C23 1.540(9) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.508(10) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.510(9) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.373(8) . ?
C27 C28 1.380(9) . ?
C27 H27 0.9500 . ?
C28 C29 1.371(8) . ?
C28 H28 0.9500 . ?
C29 C30 1.400(7) . ?
C29 H29 0.9500 . ?
C30 C31 1.456(8) . ?
C31 C32 1.379(8) . ?
C32 C33 1.386(8) . ?
C32 H32 0.9500 . ?
C33 C34 1.519(8) . ?
C34 C37 1.533(9) . ?
C34 C36 1.540(9) . ?
C34 C35 1.541(9) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 C39 1.521(8) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 C40 1.526(7) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 B2 1.625(8) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 C48 1.525(9) . ?
C41 C42 1.550(10) . ?
C41 B2 1.593(10) . ?
C41 H41 1.0000 . ?
C42 C43 1.531(10) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 C44 1.535(10) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 C45 1.531(9) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 C46 1.550(10) . ?
C45 B2 1.651(8) . ?
C45 H45 1.0000 . ?
C46 C47 1.554(12) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 C48 1.535(11) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?

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
N2 Zn1 N1 79.79(17) . . ?
N2 Zn1 Br2 119.69(12) . . ?
N1 Zn1 Br2 113.52(12) . . ?
N2 Zn1 Br1 111.71(12) . . ?
N1 Zn1 Br1 113.86(11) . . ?
Br2 Zn1 Br1 113.96(3) . . ?
N6 Zn2 N5 80.14(17) . . ?
N6 Zn2 Br3 111.60(12) . . ?
N5 Zn2 Br3 118.05(12) . . ?
N6 Zn2 Br4 120.43(12) . . ?
N5 Zn2 Br4 106.41(12) . . ?
Br3 Zn2 Br4 115.48(4) . . ?
C50 C49 Cl1 112.8(11) . . ?
C50 C49 H49A 109.0 . . ?
Cl1 C49 H49A 109.0 . . ?
C50 C49 H49B 109.0 . . ?
Cl1 C49 H49B 109.0 . . ?
H49A C49 H49B 107.8 . . ?
C49 C50 Cl2 109.8(10) . . ?
C49 C50 H50A 109.7 . . ?
Cl2 C50 H50A 109.7 . . ?
C49 C50 H50B 109.7 . . ?
Cl2 C50 H50B 109.7 . . ?
H50A C50 H50B 108.2 . . ?
C50B C49B Cl1B 116(2) . . ?
C50B C49B H49C 108.4 . . ?
Cl1B C49B H49C 108.4 . . ?
C50B C49B H49D 108.4 . . ?
Cl1B C49B H49D 108.4 . . ?
H49C C49B H49D 107.4 . . ?
C49B C50B Cl2B 104(2) . . ?
C49B C50B H50C 110.9 . . ?
Cl2B C50B H50C 110.9 . . ?
C49B C50B H50D 110.9 . . ?
Cl2B C50B H50D 110.9 . . ?
H50C C50B H50D 108.9 . . ?
C52 C51 Cl3 112.2(18) . . ?
C52 C51 H51A 109.2 . . ?
Cl3 C51 H51A 109.2 . . ?
C52 C51 H51B 109.2 . . ?
Cl3 C51 H51B 109.2 . . ?
H51A C51 H51B 107.9 . . ?
C51 C52 Cl4 106.2(17) . . ?
C51 C52 H52A 110.5 . . ?
Cl4 C52 H52A 110.5 . . ?
C51 C52 H52B 110.5 . . ?
Cl4 C52 H52B 110.5 . . ?
H52A C52 H52B 108.7 . . ?
C52B C51B Cl3B 116(2) . . ?
C52B C51B H51C 108.3 . . ?
Cl3B C51B H51C 108.3 . . ?
C52B C51B H51D 108.3 . . ?
Cl3B C51B H51D 108.3 . . ?
H51C C51B H51D 107.4 . . ?
C51B C52B Cl4B 108(2) . . ?
C51B C52B H52C 110.0 . . ?
Cl4B C52B H52C 110.0 . . ?
C51B C52B H52D 110.0 . . ?
Cl4B C52B H52D 110.0 . . ?
H52C C52B H52D 108.4 . . ?
C52C C51C Cl3C 114(2) . . ?
C52C C51C H51E 108.7 . . ?
Cl3C C51C H51E 108.7 . . ?
C52C C51C H51F 108.7 . . ?
Cl3C C51C H51F 108.7 . . ?
H51E C51C H51F 107.6 . . ?
C51C C52C Cl4C 106(2) . . ?
C51C C52C H52E 110.6 . . ?
Cl4C C52C H52E 110.6 . . ?
C51C C52C H52F 110.6 . . ?
Cl4C C52C H52F 110.6 . . ?
H52E C52C H52F 108.8 . . ?
C54 C53 Cl5 115.3(16) . . ?
C54 C53 H53A 108.4 . . ?
Cl5 C53 H53A 108.4 . . ?
C54 C53 H53B 108.4 . . ?
Cl5 C53 H53B 108.4 . . ?
H53A C53 H53B 107.5 . . ?
C53 C54 Cl6 101.7(14) . . ?
C53 C54 H54A 111.4 . . ?
Cl6 C54 H54A 111.4 . . ?
C53 C54 H54B 111.4 . . ?
Cl6 C54 H54B 111.4 . . ?
H54A C54 H54B 109.3 . . ?
C54B C53B Cl5B 114(2) . . ?
C54B C53B H53C 108.8 . . ?
Cl5B C53B H53C 108.8 . . ?
C54B C53B H53D 108.8 . . ?
Cl5B C53B H53D 108.8 . . ?
H53C C53B H53D 107.7 . . ?
C53B C54B Cl6B 109.5(18) . . ?
C53B C54B H54C 109.8 . . ?
Cl6B C54B H54C 109.8 . . ?
C53B C54B H54D 109.8 . . ?
Cl6B C54B H54D 109.8 . . ?
H54C C54B H54D 108.2 . . ?
N8 O1 B1 117.8(4) . . ?
C6 N1 C2 119.5(5) . . ?
C6 N1 Zn1 113.7(3) . . ?
C2 N1 Zn1 126.6(4) . . ?
C7 N2 N3 105.9(4) . . ?
C7 N2 Zn1 114.3(3) . . ?
N3 N2 Zn1 139.6(3) . . ?
C9 N3 N2 111.4(4) . . ?
C9 N3 C14 132.6(4) . . ?
N2 N3 C14 115.9(4) . . ?
C21 N4 B1 122.2(4) . . ?
C21 N4 H4A 106.8 . . ?
B1 N4 H4A 106.8 . . ?
C21 N4 H4B 106.8 . . ?
B1 N4 H4B 106.8 . . ?
H4A N4 H4B 106.6 . . ?
C30 N5 C26 119.7(5) . . ?
C30 N5 Zn2 113.0(4) . . ?
C26 N5 Zn2 127.2(4) . . ?
N7 N6 C31 106.0(4) . . ?
N7 N6 Zn2 138.8(3) . . ?
C31 N6 Zn2 113.8(3) . . ?
N6 N7 C33 111.2(4) . . ?
N6 N7 C38 116.5(4) . . ?
C33 N7 C38 132.3(5) . . ?
O1 N8 B2 117.7(4) . . ?
O1 N8 H8A 107.9 . . ?
B2 N8 H8A 107.9 . . ?
O1 N8 H8B 107.9 . . ?
B2 N8 H8B 107.9 . . ?
H8A N8 H8B 107.2 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 120.1(5) . . ?
N1 C2 C1 116.4(5) . . ?
C3 C2 C1 123.5(5) . . ?
C4 C3 C2 120.4(5) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.3(5) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 116.8(5) . . ?
C6 C5 H5 121.6 . . ?
C4 C5 H5 121.6 . . ?
N1 C6 C5 122.9(5) . . ?
N1 C6 C7 114.5(4) . . ?
C5 C6 C7 122.6(5) . . ?
N2 C7 C8 110.2(5) . . ?
N2 C7 C6 117.3(5) . . ?
C8 C7 C6 132.4(5) . . ?
C9 C8 C7 106.2(5) . . ?
C9 C8 H8 126.9 . . ?
C7 C8 H8 126.9 . . ?
N3 C9 C8 106.2(5) . . ?
N3 C9 C10 125.1(5) . . ?
C8 C9 C10 128.6(5) . . ?
C13 C10 C9 111.1(4) . . ?
C13 C10 C12 107.8(5) . . ?
C9 C10 C12 107.8(5) . . ?
C13 C10 C11 110.2(5) . . ?
C9 C10 C11 111.2(5) . . ?
C12 C10 C11 108.7(5) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C15 112.6(4) . . ?
N3 C14 H14A 109.1 . . ?
C15 C14 H14A 109.1 . . ?
N3 C14 H14B 109.1 . . ?
C15 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 C16 110.4(4) . . ?
C14 C15 H15A 109.6 . . ?
C16 C15 H15A 109.6 . . ?
C14 C15 H15B 109.6 . . ?
C16 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C15 C16 B1 114.7(4) . . ?
C15 C16 H16A 108.6 . . ?
B1 C16 H16A 108.6 . . ?
C15 C16 H16B 108.6 . . ?
B1 C16 H16B 108.6 . . ?
H16A C16 H16B 107.6 . . ?
C24 C17 C18 109.2(5) . . ?
C24 C17 B1 112.8(5) . . ?
C18 C17 B1 117.4(5) . . ?
C24 C17 H17 105.5 . . ?
C18 C17 H17 105.5 . . ?
B1 C17 H17 105.5 . . ?
C19 C18 C17 117.2(5) . . ?
C19 C18 H18A 108.0 . . ?
C17 C18 H18A 108.0 . . ?
C19 C18 H18B 108.0 . . ?
C17 C18 H18B 108.0 . . ?
H18A C18 H18B 107.2 . . ?
C20 C19 C18 118.8(5) . . ?
C20 C19 H19A 107.6 . . ?
C18 C19 H19A 107.6 . . ?
C20 C19 H19B 107.6 . . ?
C18 C19 H19B 107.6 . . ?
H19A C19 H19B 107.1 . . ?
C19 C20 C21 115.9(5) . . ?
C19 C20 H20A 108.3 . . ?
C21 C20 H20A 108.3 . . ?
C19 C20 H20B 108.3 . . ?
C21 C20 H20B 108.3 . . ?
H20A C20 H20B 107.4 . . ?
N4 C21 C22 113.1(5) . . ?
N4 C21 C20 110.1(5) . . ?
C22 C21 C20 115.6(5) . . ?
N4 C21 H21 105.7 . . ?
C22 C21 H21 105.7 . . ?
C20 C21 H21 105.7 . . ?
C21 C22 C23 116.4(5) . . ?
C21 C22 H22A 108.2 . . ?
C23 C22 H22A 108.2 . . ?
C21 C22 H22B 108.2 . . ?
C23 C22 H22B 108.2 . . ?
H22A C22 H22B 107.3 . . ?
C24 C23 C22 117.5(5) . . ?
C24 C23 H23A 107.9 . . ?
C22 C23 H23A 107.9 . . ?
C24 C23 H23B 107.9 . . ?
C22 C23 H23B 107.9 . . ?
H23A C23 H23B 107.2 . . ?
C23 C24 C17 115.7(5) . . ?
C23 C24 H24A 108.3 . . ?
C17 C24 H24A 108.3 . . ?
C23 C24 H24B 108.3 . . ?
C17 C24 H24B 108.3 . . ?
H24A C24 H24B 107.4 . . ?
C26 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C26 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N5 C26 C27 121.5(6) . . ?
N5 C26 C25 116.7(5) . . ?
C27 C26 C25 121.8(6) . . ?
C26 C27 C28 119.0(6) . . ?
C26 C27 H27 120.5 . . ?
C28 C27 H27 120.5 . . ?
C29 C28 C27 120.5(5) . . ?
C29 C28 H28 119.7 . . ?
C27 C28 H28 119.7 . . ?
C28 C29 C30 118.0(5) . . ?
C28 C29 H29 121.0 . . ?
C30 C29 H29 121.0 . . ?
N5 C30 C29 121.4(5) . . ?
N5 C30 C31 116.1(4) . . ?
C29 C30 C31 122.3(5) . . ?
N6 C31 C32 110.1(5) . . ?
N6 C31 C30 116.8(5) . . ?
C32 C31 C30 132.6(5) . . ?
C31 C32 C33 106.3(5) . . ?
C31 C32 H32 126.8 . . ?
C33 C32 H32 126.8 . . ?
N7 C33 C32 106.3(5) . . ?
N7 C33 C34 126.4(5) . . ?
C32 C33 C34 127.1(5) . . ?
C33 C34 C37 110.2(5) . . ?
C33 C34 C36 111.2(5) . . ?
C37 C34 C36 110.8(5) . . ?
C33 C34 C35 107.9(5) . . ?
C37 C34 C35 108.1(5) . . ?
C36 C34 C35 108.5(6) . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C34 C37 H37A 109.5 . . ?
C34 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C34 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
N7 C38 C39 114.8(4) . . ?
N7 C38 H38A 108.6 . . ?
C39 C38 H38A 108.6 . . ?
N7 C38 H38B 108.6 . . ?
C39 C38 H38B 108.6 . . ?
H38A C38 H38B 107.5 . . ?
C38 C39 C40 109.1(4) . . ?
C38 C39 H39A 109.9 . . ?
C40 C39 H39A 109.9 . . ?
C38 C39 H39B 109.9 . . ?
C40 C39 H39B 109.9 . . ?
H39A C39 H39B 108.3 . . ?
C39 C40 B2 119.8(5) . . ?
C39 C40 H40A 107.4 . . ?
B2 C40 H40A 107.4 . . ?
C39 C40 H40B 107.4 . . ?
B2 C40 H40B 107.4 . . ?
H40A C40 H40B 106.9 . . ?
C48 C41 C42 112.9(6) . . ?
C48 C41 B2 106.8(5) . . ?
C42 C41 B2 112.4(5) . . ?
C48 C41 H41 108.2 . . ?
C42 C41 H41 108.2 . . ?
B2 C41 H41 108.2 . . ?
C43 C42 C41 113.7(6) . . ?
C43 C42 H42A 108.8 . . ?
C41 C42 H42A 108.8 . . ?
C43 C42 H42B 108.8 . . ?
C41 C42 H42B 108.8 . . ?
H42A C42 H42B 107.7 . . ?
C42 C43 C44 116.3(6) . . ?
C42 C43 H43A 108.2 . . ?
C44 C43 H43A 108.2 . . ?
C42 C43 H43B 108.2 . . ?
C44 C43 H43B 108.2 . . ?
H43A C43 H43B 107.4 . . ?
C45 C44 C43 114.3(6) . . ?
C45 C44 H44A 108.7 . . ?
C43 C44 H44A 108.7 . . ?
C45 C44 H44B 108.7 . . ?
C43 C44 H44B 108.7 . . ?
H44A C44 H44B 107.6 . . ?
C44 C45 C46 111.8(6) . . ?
C44 C45 B2 112.6(5) . . ?
C46 C45 B2 107.1(5) . . ?
C44 C45 H45 108.4 . . ?
C46 C45 H45 108.4 . . ?
B2 C45 H45 108.4 . . ?
C45 C46 C47 113.9(6) . . ?
C45 C46 H46A 108.8 . . ?
C47 C46 H46A 108.8 . . ?
C45 C46 H46B 108.8 . . ?
C47 C46 H46B 108.8 . . ?
H46A C46 H46B 107.7 . . ?
C48 C47 C46 114.8(6) . . ?
C48 C47 H47A 108.6 . . ?
C46 C47 H47A 108.6 . . ?
C48 C47 H47B 108.6 . . ?
C46 C47 H47B 108.6 . . ?
H47A C47 H47B 107.6 . . ?
C41 C48 C47 116.4(6) . . ?
C41 C48 H48A 108.2 . . ?
C47 C48 H48A 108.2 . . ?
C41 C48 H48B 108.2 . . ?
C47 C48 H48B 108.2 . . ?
H48A C48 H48B 107.3 . . ?
O1 B1 C17 115.3(4) . . ?
O1 B1 C16 106.2(4) . . ?
C17 B1 C16 114.0(4) . . ?
O1 B1 N4 102.4(4) . . ?
C17 B1 N4 112.2(5) . . ?
C16 B1 N4 105.7(4) . . ?
C41 B2 C40 118.9(5) . . ?
C41 B2 N8 109.4(5) . . ?
C40 B2 N8 106.5(5) . . ?
C41 B2 C45 105.9(5) . . ?
C40 B2 C45 112.0(5) . . ?
N8 B2 C45 103.2(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C49 C50 Cl2 173.2(11) . . . . ?
Cl1B C49B C50B Cl2B 84(4) . . . . ?
Cl3 C51 C52 Cl4 76(2) . . . . ?
Cl3B C51B C52B Cl4B 116(3) . . . . ?
Cl3C C51C C52C Cl4C 44(6) . . . . ?
Cl5 C53 C54 Cl6 166.3(18) . . . . ?
Cl5B C53B C54B Cl6B 141(2) . . . . ?
C7 N2 N3 C9 0.7(5) . . . . ?
Zn1 N2 N3 C9 174.6(4) . . . . ?
C7 N2 N3 C14 177.5(4) . . . . ?
Zn1 N2 N3 C14 -8.6(7) . . . . ?
C31 N6 N7 C33 0.8(5) . . . . ?
Zn2 N6 N7 C33 -164.0(4) . . . . ?
C31 N6 N7 C38 178.5(4) . . . . ?
Zn2 N6 N7 C38 13.6(7) . . . . ?
B1 O1 N8 B2 146.4(5) . . . . ?
C6 N1 C2 C3 1.1(7) . . . . ?
Zn1 N1 C2 C3 -171.8(4) . . . . ?
C6 N1 C2 C1 -179.0(5) . . . . ?
Zn1 N1 C2 C1 8.1(7) . . . . ?
N1 C2 C3 C4 0.5(8) . . . . ?
C1 C2 C3 C4 -179.3(5) . . . . ?
C2 C3 C4 C5 -2.5(8) . . . . ?
C3 C4 C5 C6 2.7(8) . . . . ?
C2 N1 C6 C5 -0.8(7) . . . . ?
Zn1 N1 C6 C5 173.0(4) . . . . ?
C2 N1 C6 C7 179.4(4) . . . . ?
Zn1 N1 C6 C7 -6.8(5) . . . . ?
C4 C5 C6 N1 -1.1(7) . . . . ?
C4 C5 C6 C7 178.7(5) . . . . ?
N3 N2 C7 C8 -1.0(5) . . . . ?
Zn1 N2 C7 C8 -176.7(3) . . . . ?
N3 N2 C7 C6 177.3(4) . . . . ?
Zn1 N2 C7 C6 1.7(5) . . . . ?
N1 C6 C7 N2 3.6(6) . . . . ?
C5 C6 C7 N2 -176.3(4) . . . . ?
N1 C6 C7 C8 -178.5(5) . . . . ?
C5 C6 C7 C8 1.6(8) . . . . ?
N2 C7 C8 C9 1.0(6) . . . . ?
C6 C7 C8 C9 -177.1(5) . . . . ?
N2 N3 C9 C8 -0.1(6) . . . . ?
C14 N3 C9 C8 -176.2(5) . . . . ?
N2 N3 C9 C10 -177.9(4) . . . . ?
C14 N3 C9 C10 6.1(8) . . . . ?
C7 C8 C9 N3 -0.5(6) . . . . ?
C7 C8 C9 C10 177.1(5) . . . . ?
N3 C9 C10 C13 63.9(7) . . . . ?
C8 C9 C10 C13 -113.3(6) . . . . ?
N3 C9 C10 C12 -178.2(5) . . . . ?
C8 C9 C10 C12 4.6(8) . . . . ?
N3 C9 C10 C11 -59.1(7) . . . . ?
C8 C9 C10 C11 123.7(6) . . . . ?
C9 N3 C14 C15 100.2(6) . . . . ?
N2 N3 C14 C15 -75.8(5) . . . . ?
N3 C14 C15 C16 173.4(4) . . . . ?
C14 C15 C16 B1 -173.9(5) . . . . ?
C24 C17 C18 C19 -105.0(6) . . . . ?
B1 C17 C18 C19 25.1(8) . . . . ?
C17 C18 C19 C20 59.9(7) . . . . ?
C18 C19 C20 C21 -58.8(8) . . . . ?
B1 N4 C21 C22 -52.3(7) . . . . ?
B1 N4 C21 C20 78.7(6) . . . . ?
C19 C20 C21 N4 -29.6(8) . . . . ?
C19 C20 C21 C22 100.1(7) . . . . ?
N4 C21 C22 C23 85.0(7) . . . . ?
C20 C21 C22 C23 -43.3(8) . . . . ?
C21 C22 C23 C24 -66.6(8) . . . . ?
C22 C23 C24 C17 56.7(8) . . . . ?
C18 C17 C24 C23 54.5(7) . . . . ?
B1 C17 C24 C23 -78.0(7) . . . . ?
C30 N5 C26 C27 -0.4(8) . . . . ?
Zn2 N5 C26 C27 176.8(4) . . . . ?
C30 N5 C26 C25 -178.0(5) . . . . ?
Zn2 N5 C26 C25 -0.8(8) . . . . ?
N5 C26 C27 C28 0.4(9) . . . . ?
C25 C26 C27 C28 177.9(6) . . . . ?
C26 C27 C28 C29 -0.2(9) . . . . ?
C27 C28 C29 C30 -0.1(8) . . . . ?
C26 N5 C30 C29 0.1(7) . . . . ?
Zn2 N5 C30 C29 -177.4(4) . . . . ?
C26 N5 C30 C31 175.3(5) . . . . ?
Zn2 N5 C30 C31 -2.3(5) . . . . ?
C28 C29 C30 N5 0.1(8) . . . . ?
C28 C29 C30 C31 -174.8(5) . . . . ?
N7 N6 C31 C32 -0.3(5) . . . . ?
Zn2 N6 C31 C32 168.9(3) . . . . ?
N7 N6 C31 C30 -172.8(4) . . . . ?
Zn2 N6 C31 C30 -3.6(5) . . . . ?
N5 C30 C31 N6 4.0(6) . . . . ?
C29 C30 C31 N6 179.1(4) . . . . ?
N5 C30 C31 C32 -166.4(5) . . . . ?
C29 C30 C31 C32 8.7(8) . . . . ?
N6 C31 C32 C33 -0.3(6) . . . . ?
C30 C31 C32 C33 170.5(5) . . . . ?
N6 N7 C33 C32 -1.0(6) . . . . ?
C38 N7 C33 C32 -178.2(5) . . . . ?
N6 N7 C33 C34 173.8(5) . . . . ?
C38 N7 C33 C34 -3.4(9) . . . . ?
C31 C32 C33 N7 0.8(6) . . . . ?
C31 C32 C33 C34 -174.0(5) . . . . ?
N7 C33 C34 C37 -64.2(7) . . . . ?
C32 C33 C34 C37 109.6(6) . . . . ?
N7 C33 C34 C36 59.1(7) . . . . ?
C32 C33 C34 C36 -127.1(6) . . . . ?
N7 C33 C34 C35 178.0(5) . . . . ?
C32 C33 C34 C35 -8.2(8) . . . . ?
N6 N7 C38 C39 77.6(6) . . . . ?
C33 N7 C38 C39 -105.3(7) . . . . ?
N7 C38 C39 C40 -179.5(5) . . . . ?
C38 C39 C40 B2 -177.7(5) . . . . ?
C48 C41 C42 C43 67.5(8) . . . . ?
B2 C41 C42 C43 -53.4(8) . . . . ?
C41 C42 C43 C44 43.9(9) . . . . ?
C42 C43 C44 C45 -42.8(9) . . . . ?
C43 C44 C45 C46 -70.7(8) . . . . ?
C43 C44 C45 B2 50.0(8) . . . . ?
C44 C45 C46 C47 70.1(8) . . . . ?
B2 C45 C46 C47 -53.8(8) . . . . ?
C45 C46 C47 C48 41.6(10) . . . . ?
C42 C41 C48 C47 -68.3(9) . . . . ?
B2 C41 C48 C47 55.8(8) . . . . ?
C46 C47 C48 C41 -42.6(10) . . . . ?
N8 O1 B1 C17 -4.3(7) . . . . ?
N8 O1 B1 C16 -131.6(4) . . . . ?
N8 O1 B1 N4 117.8(4) . . . . ?
C24 C17 B1 O1 -167.5(5) . . . . ?
C18 C17 B1 O1 64.2(7) . . . . ?
C24 C17 B1 C16 -44.3(7) . . . . ?
C18 C17 B1 C16 -172.6(5) . . . . ?
C24 C17 B1 N4 75.9(6) . . . . ?
C18 C17 B1 N4 -52.5(7) . . . . ?
C15 C16 B1 O1 -42.4(6) . . . . ?
C15 C16 B1 C17 -170.4(5) . . . . ?
C15 C16 B1 N4 65.9(6) . . . . ?
C21 N4 B1 O1 -142.5(4) . . . . ?
C21 N4 B1 C17 -18.4(7) . . . . ?
C21 N4 B1 C16 106.5(5) . . . . ?
C48 C41 B2 C40 60.4(7) . . . . ?
C42 C41 B2 C40 -175.2(5) . . . . ?
C48 C41 B2 N8 -177.0(5) . . . . ?
C42 C41 B2 N8 -52.7(7) . . . . ?
C48 C41 B2 C45 -66.5(6) . . . . ?
C42 C41 B2 C45 57.9(7) . . . . ?
C39 C40 B2 C41 55.4(8) . . . . ?
C39 C40 B2 N8 -68.6(7) . . . . ?
C39 C40 B2 C45 179.3(5) . . . . ?
O1 N8 B2 C41 -44.7(6) . . . . ?
O1 N8 B2 C40 85.0(6) . . . . ?
O1 N8 B2 C45 -157.0(5) . . . . ?
C44 C45 B2 C41 -56.7(7) . . . . ?
C46 C45 B2 C41 66.7(6) . . . . ?
C44 C45 B2 C40 172.4(6) . . . . ?
C46 C45 B2 C40 -64.3(7) . . . . ?
C44 C45 B2 N8 58.3(7) . . . . ?
C46 C45 B2 N8 -178.4(5) . . . . ?

_refine_diff_density_max         1.144
_refine_diff_density_min         -1.003
_refine_diff_density_rms         0.126


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_JK4210_0m
_database_code_depnum_ccdc_archive 'CCDC 1941368'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller '
;Purdue University
United States of America
;
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H38 B Br Fe N4'
_chemical_formula_weight         529.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   21.6707(4)
_cell_length_b                   13.3677(2)
_cell_length_c                   18.9165(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.2654(8)
_cell_angle_gamma                90
_cell_volume                     5232.95(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9964
_cell_measurement_theta_min      3.9361
_cell_measurement_theta_max      80.6618

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             2208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    6.530
_shelx_estimated_absorpt_T_min   0.222
_shelx_estimated_absorpt_T_max   0.534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5407
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18479
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.937
_diffrn_reflns_theta_max         80.935
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             5234
_reflns_number_gt                4751
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Apex3 v2017.3-0 (Bruker, 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev937 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0281P)²+7.2848P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.000059(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5234
_refine_ls_number_parameters     285
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0727
_refine_ls_wR_factor_gt          0.0710
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.58116(12) 0.3111(2) 0.15796(13) 0.0431(6) Uani 1 1 d . . . . .
H1A H 0.544391 0.329014 0.175565 0.065 Uiso 1 1 calc R U . . .
H1B H 0.621038 0.337680 0.192208 0.065 Uiso 1 1 calc R U . . .
H1C H 0.584234 0.238136 0.155453 0.065 Uiso 1 1 calc R U . . .
C2 C 0.57173(10) 0.35452(16) 0.08288(12) 0.0272(4) Uani 1 1 d . . . . .
C3 C 0.62078(10) 0.40547(16) 0.06475(13) 0.0306(5) Uani 1 1 d . . . . .
H3 H 0.661378 0.414950 0.101014 0.037 Uiso 1 1 calc R U . . .
C4 C 0.61060(11) 0.44224(16) -0.00573(14) 0.0328(5) Uani 1 1 d . . . . .
H4 H 0.643975 0.477392 -0.018299 0.039 Uiso 1 1 calc R U . . .
C5 C 0.55112(10) 0.42752(16) -0.05833(13) 0.0273(4) Uani 1 1 d . . . . .
H5 H 0.543060 0.451736 -0.107455 0.033 Uiso 1 1 calc R U . . .
C6 C 0.50393(10) 0.37652(14) -0.03706(11) 0.0219(4) Uani 1 1 d . . . . .
C7 C 0.43940(9) 0.35800(14) -0.08805(11) 0.0202(4) Uani 1 1 d . . . . .
C8 C 0.41258(10) 0.37502(15) -0.16352(11) 0.0253(4) Uani 1 1 d . . . . .
H8 H 0.433464 0.404069 -0.196150 0.030 Uiso 1 1 calc R U . . .
C9 C 0.34956(10) 0.34131(14) -0.18162(11) 0.0216(4) Uani 1 1 d . . . . .
C10 C 0.29817(10) 0.34288(16) -0.25608(11) 0.0262(4) Uani 1 1 d . . . . .
C11 C 0.32710(13) 0.3925(2) -0.31229(13) 0.0410(6) Uani 1 1 d . . . . .
H11A H 0.294681 0.393754 -0.361062 0.062 Uiso 1 1 calc R U . . .
H11B H 0.364861 0.354254 -0.315212 0.062 Uiso 1 1 calc R U . . .
H11C H 0.340232 0.461046 -0.296455 0.062 Uiso 1 1 calc R U . . .
C12 C 0.23922(12) 0.40434(19) -0.25243(13) 0.0364(5) Uani 1 1 d . . . . .
H12A H 0.208063 0.408502 -0.301927 0.055 Uiso 1 1 calc R U . . .
H12B H 0.253144 0.471852 -0.234439 0.055 Uiso 1 1 calc R U . . .
H12C H 0.218870 0.371842 -0.218590 0.055 Uiso 1 1 calc R U . . .
C13 C 0.27794(12) 0.23616(18) -0.28384(13) 0.0344(5) Uani 1 1 d . . . . .
H13A H 0.249733 0.238912 -0.334995 0.052 Uiso 1 1 calc R U . . .
H13B H 0.254700 0.204939 -0.252366 0.052 Uiso 1 1 calc R U . . .
H13C H 0.316519 0.196651 -0.281838 0.052 Uiso 1 1 calc R U . . .
C14 C 0.28269(9) 0.26503(15) -0.10289(11) 0.0218(4) Uani 1 1 d . . . . .
H14A H 0.254135 0.235397 -0.148991 0.026 Uiso 1 1 calc R U . . .
H14B H 0.258898 0.320631 -0.088224 0.026 Uiso 1 1 calc R U . . .
C15 C 0.29812(9) 0.18607(14) -0.04231(10) 0.0193(4) Uani 1 1 d . . . . .
H15A H 0.256862 0.162026 -0.036018 0.023 Uiso 1 1 calc R U . . .
H15B H 0.322642 0.218546 0.004668 0.023 Uiso 1 1 calc R U . . .
C16 C 0.33670(9) 0.09485(14) -0.05441(11) 0.0204(4) Uani 1 1 d . . . . .
H16A H 0.363806 0.115170 -0.085856 0.024 Uiso 1 1 calc R U . . .
H16B H 0.305962 0.043472 -0.081900 0.024 Uiso 1 1 calc R U . . .
C17 C 0.40465(10) -0.06998(15) 0.00857(11) 0.0232(4) Uani 1 1 d . . . . .
H17 H 0.424411 -0.068719 -0.032947 0.028 Uiso 1 1 calc R U . . .
C18 C 0.34418(11) -0.13710(15) -0.01499(12) 0.0277(5) Uani 1 1 d . . . . .
H18A H 0.358460 -0.207271 -0.016107 0.033 Uiso 1 1 calc R U . . .
H18B H 0.318993 -0.118771 -0.066120 0.033 Uiso 1 1 calc R U . . .
C19 C 0.29876(12) -0.13208(16) 0.03425(13) 0.0321(5) Uani 1 1 d . . . . .
H19A H 0.255758 -0.157563 0.005422 0.038 Uiso 1 1 calc R U . . .
H19B H 0.315761 -0.177386 0.077016 0.038 Uiso 1 1 calc R U . . .
C20 C 0.29021(10) -0.02777(16) 0.06351(12) 0.0260(4) Uani 1 1 d . . . . .
H20A H 0.271741 -0.035246 0.105216 0.031 Uiso 1 1 calc R U . . .
H20B H 0.258447 0.009609 0.023827 0.031 Uiso 1 1 calc R U . . .
C21 C 0.35228(9) 0.03482(14) 0.09000(11) 0.0207(4) Uani 1 1 d . . . . .
H21 H 0.340184 0.103461 0.102206 0.025 Uiso 1 1 calc R U . . .
C22 C 0.40125(11) -0.00891(18) 0.15983(12) 0.0310(5) Uani 1 1 d . . . . .
H22A H 0.435253 0.041719 0.180064 0.037 Uiso 1 1 calc R U . . .
H22B H 0.378686 -0.020677 0.197549 0.037 Uiso 1 1 calc R U . . .
C23 C 0.43405(12) -0.10708(19) 0.14814(13) 0.0383(6) Uani 1 1 d . . . . .
H23A H 0.472293 -0.118374 0.191557 0.046 Uiso 1 1 calc R U . . .
H23B H 0.403617 -0.163025 0.146015 0.046 Uiso 1 1 calc R U . . .
C24 C 0.45567(11) -0.10952(17) 0.07786(13) 0.0308(5) Uani 1 1 d . . . . .
H24A H 0.466516 -0.179298 0.068625 0.037 Uiso 1 1 calc R U . . .
H24B H 0.495453 -0.068994 0.086376 0.037 Uiso 1 1 calc R U . . .
B1 B 0.38342(10) 0.04421(16) 0.02163(12) 0.0196(4) Uani 1 1 d . . . . .
N1 N 0.51386(8) 0.34055(12) 0.03231(9) 0.0222(3) Uani 1 1 d . . . . .
N2 N 0.39562(7) 0.31587(12) -0.06009(9) 0.0194(3) Uani 1 1 d . . . . .
N3 N 0.34104(8) 0.30525(12) -0.11761(9) 0.0193(3) Uani 1 1 d . . . . .
N4 N 0.44643(8) 0.11685(13) 0.04726(10) 0.0232(4) Uani 1 1 d . . . . .
H4A H 0.471137 0.104938 0.016772 0.028 Uiso 1 1 calc R U . . .
H4B H 0.470060 0.098222 0.093672 0.028 Uiso 1 1 calc R U . . .
Fe1 Fe 0.43140(2) 0.26580(2) 0.04837(2) 0.01981(9) Uani 1 1 d . . . . .
Br1 Br 0.39385(2) 0.34799(2) 0.14042(2) 0.03193(8) 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 1.491(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 N1 1.346(3) . ?
C2 C3 1.388(3) . ?
C3 C4 1.376(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9500 . ?
C6 N1 1.353(3) . ?
C6 C7 1.465(3) . ?
C7 N2 1.340(2) . ?
C7 C8 1.391(3) . ?
C8 C9 1.381(3) . ?
C8 H8 0.9500 . ?
C9 N3 1.366(2) . ?
C9 C10 1.514(3) . ?
C10 C11 1.536(3) . ?
C10 C12 1.538(3) . ?
C10 C13 1.538(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 N3 1.475(2) . ?
C14 C15 1.520(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.534(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 B1 1.640(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C24 1.536(3) . ?
C17 C18 1.541(3) . ?
C17 B1 1.634(3) . ?
C17 H17 1.0000 . ?
C18 C19 1.544(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.532(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.536(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.543(3) . ?
C21 B1 1.631(3) . ?
C21 H21 1.0000 . ?
C22 C23 1.539(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.536(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
B1 N4 1.628(3) . ?
N1 Fe1 2.1462(17) . ?
N2 N3 1.356(2) . ?
N2 Fe1 2.0770(16) . ?
N4 Fe1 2.0187(17) . ?
N4 H4A 0.9100 . ?
N4 H4B 0.9100 . ?
Fe1 Br1 2.3963(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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 120.8(2) . . ?
N1 C2 C1 117.29(19) . . ?
C3 C2 C1 121.9(2) . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 119.4(2) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 118.0(2) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
N1 C6 C5 122.56(19) . . ?
N1 C6 C7 115.11(17) . . ?
C5 C6 C7 122.33(19) . . ?
N2 C7 C8 110.16(17) . . ?
N2 C7 C6 117.41(17) . . ?
C8 C7 C6 132.42(18) . . ?
C9 C8 C7 106.40(17) . . ?
C9 C8 H8 126.8 . . ?
C7 C8 H8 126.8 . . ?
N3 C9 C8 106.22(17) . . ?
N3 C9 C10 125.01(18) . . ?
C8 C9 C10 128.77(18) . . ?
C9 C10 C11 108.13(18) . . ?
C9 C10 C12 110.92(17) . . ?
C11 C10 C12 108.41(19) . . ?
C9 C10 C13 111.17(18) . . ?
C11 C10 C13 107.31(18) . . ?
C12 C10 C13 110.77(19) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C15 112.73(15) . . ?
N3 C14 H14A 109.0 . . ?
C15 C14 H14A 109.0 . . ?
N3 C14 H14B 109.0 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 C16 116.56(16) . . ?
C14 C15 H15A 108.2 . . ?
C16 C15 H15A 108.2 . . ?
C14 C15 H15B 108.2 . . ?
C16 C15 H15B 108.2 . . ?
H15A C15 H15B 107.3 . . ?
C15 C16 B1 114.79(15) . . ?
C15 C16 H16A 108.6 . . ?
B1 C16 H16A 108.6 . . ?
C15 C16 H16B 108.6 . . ?
B1 C16 H16B 108.6 . . ?
H16A C16 H16B 107.5 . . ?
C24 C17 C18 112.42(18) . . ?
C24 C17 B1 110.86(17) . . ?
C18 C17 B1 109.52(16) . . ?
C24 C17 H17 108.0 . . ?
C18 C17 H17 108.0 . . ?
B1 C17 H17 108.0 . . ?
C17 C18 C19 116.10(17) . . ?
C17 C18 H18A 108.3 . . ?
C19 C18 H18A 108.3 . . ?
C17 C18 H18B 108.3 . . ?
C19 C18 H18B 108.3 . . ?
H18A C18 H18B 107.4 . . ?
C20 C19 C18 115.12(17) . . ?
C20 C19 H19A 108.5 . . ?
C18 C19 H19A 108.5 . . ?
C20 C19 H19B 108.5 . . ?
C18 C19 H19B 108.5 . . ?
H19A C19 H19B 107.5 . . ?
C19 C20 C21 115.18(17) . . ?
C19 C20 H20A 108.5 . . ?
C21 C20 H20A 108.5 . . ?
C19 C20 H20B 108.5 . . ?
C21 C20 H20B 108.5 . . ?
H20A C20 H20B 107.5 . . ?
C20 C21 C22 112.71(17) . . ?
C20 C21 B1 108.14(16) . . ?
C22 C21 B1 111.51(16) . . ?
C20 C21 H21 108.1 . . ?
C22 C21 H21 108.1 . . ?
B1 C21 H21 108.1 . . ?
C23 C22 C21 115.44(18) . . ?
C23 C22 H22A 108.4 . . ?
C21 C22 H22A 108.4 . . ?
C23 C22 H22B 108.4 . . ?
C21 C22 H22B 108.4 . . ?
H22A C22 H22B 107.5 . . ?
C24 C23 C22 114.52(19) . . ?
C24 C23 H23A 108.6 . . ?
C22 C23 H23A 108.6 . . ?
C24 C23 H23B 108.6 . . ?
C22 C23 H23B 108.6 . . ?
H23A C23 H23B 107.6 . . ?
C23 C24 C17 113.83(18) . . ?
C23 C24 H24A 108.8 . . ?
C17 C24 H24A 108.8 . . ?
C23 C24 H24B 108.8 . . ?
C17 C24 H24B 108.8 . . ?
H24A C24 H24B 107.7 . . ?
N4 B1 C21 108.52(16) . . ?
N4 B1 C17 110.69(15) . . ?
C21 B1 C17 104.43(16) . . ?
N4 B1 C16 105.07(15) . . ?
C21 B1 C16 115.74(16) . . ?
C17 B1 C16 112.41(16) . . ?
C2 N1 C6 119.10(18) . . ?
C2 N1 Fe1 127.12(14) . . ?
C6 N1 Fe1 113.77(13) . . ?
C7 N2 N3 106.17(15) . . ?
C7 N2 Fe1 115.15(13) . . ?
N3 N2 Fe1 137.71(12) . . ?
N2 N3 C9 111.04(16) . . ?
N2 N3 C14 118.64(15) . . ?
C9 N3 C14 130.19(16) . . ?
B1 N4 Fe1 117.89(12) . . ?
B1 N4 H4A 107.8 . . ?
Fe1 N4 H4A 107.8 . . ?
B1 N4 H4B 107.8 . . ?
Fe1 N4 H4B 107.8 . . ?
H4A N4 H4B 107.2 . . ?
N4 Fe1 N2 108.77(7) . . ?
N4 Fe1 N1 108.31(6) . . ?
N2 Fe1 N1 78.03(6) . . ?
N4 Fe1 Br1 123.39(5) . . ?
N2 Fe1 Br1 117.53(5) . . ?
N1 Fe1 Br1 111.46(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 -0.1(3) . . . . ?
C1 C2 C3 C4 178.4(2) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 N1 -0.4(3) . . . . ?
C4 C5 C6 C7 179.34(19) . . . . ?
N1 C6 C7 N2 5.5(3) . . . . ?
C5 C6 C7 N2 -174.18(18) . . . . ?
N1 C6 C7 C8 -173.8(2) . . . . ?
C5 C6 C7 C8 6.4(3) . . . . ?
N2 C7 C8 C9 0.0(2) . . . . ?
C6 C7 C8 C9 179.4(2) . . . . ?
C7 C8 C9 N3 -0.4(2) . . . . ?
C7 C8 C9 C10 179.17(19) . . . . ?
N3 C9 C10 C11 178.2(2) . . . . ?
C8 C9 C10 C11 -1.3(3) . . . . ?
N3 C9 C10 C12 59.5(3) . . . . ?
C8 C9 C10 C12 -120.0(2) . . . . ?
N3 C9 C10 C13 -64.3(3) . . . . ?
C8 C9 C10 C13 116.3(2) . . . . ?
N3 C14 C15 C16 -57.2(2) . . . . ?
C14 C15 C16 B1 149.66(17) . . . . ?
C24 C17 C18 C19 73.1(2) . . . . ?
B1 C17 C18 C19 -50.6(2) . . . . ?
C17 C18 C19 C20 38.4(3) . . . . ?
C18 C19 C20 C21 -41.5(3) . . . . ?
C19 C20 C21 C22 -67.0(2) . . . . ?
C19 C20 C21 B1 56.7(2) . . . . ?
C20 C21 C22 C23 70.4(2) . . . . ?
B1 C21 C22 C23 -51.5(2) . . . . ?
C21 C22 C23 C24 42.8(3) . . . . ?
C22 C23 C24 C17 -45.4(3) . . . . ?
C18 C17 C24 C23 -66.0(2) . . . . ?
B1 C17 C24 C23 56.9(2) . . . . ?
C20 C21 B1 N4 176.09(15) . . . . ?
C22 C21 B1 N4 -59.4(2) . . . . ?
C20 C21 B1 C17 -65.82(19) . . . . ?
C22 C21 B1 C17 58.6(2) . . . . ?
C20 C21 B1 C16 58.3(2) . . . . ?
C22 C21 B1 C16 -177.22(17) . . . . ?
C24 C17 B1 N4 54.9(2) . . . . ?
C18 C17 B1 N4 179.54(16) . . . . ?
C24 C17 B1 C21 -61.7(2) . . . . ?
C18 C17 B1 C21 62.9(2) . . . . ?
C24 C17 B1 C16 172.07(16) . . . . ?
C18 C17 B1 C16 -63.3(2) . . . . ?
C15 C16 B1 N4 -78.04(19) . . . . ?
C15 C16 B1 C21 41.6(2) . . . . ?
C15 C16 B1 C17 161.50(16) . . . . ?
C3 C2 N1 C6 0.3(3) . . . . ?
C1 C2 N1 C6 -178.3(2) . . . . ?
C3 C2 N1 Fe1 -179.36(15) . . . . ?
C1 C2 N1 Fe1 2.0(3) . . . . ?
C5 C6 N1 C2 -0.1(3) . . . . ?
C7 C6 N1 C2 -179.77(17) . . . . ?
C5 C6 N1 Fe1 179.66(15) . . . . ?
C7 C6 N1 Fe1 -0.1(2) . . . . ?
C8 C7 N2 N3 0.4(2) . . . . ?
C6 C7 N2 N3 -179.07(16) . . . . ?
C8 C7 N2 Fe1 171.18(13) . . . . ?
C6 C7 N2 Fe1 -8.3(2) . . . . ?
C7 N2 N3 C9 -0.7(2) . . . . ?
Fe1 N2 N3 C9 -168.21(14) . . . . ?
C7 N2 N3 C14 -176.94(16) . . . . ?
Fe1 N2 N3 C14 15.6(3) . . . . ?
C8 C9 N3 N2 0.7(2) . . . . ?
C10 C9 N3 N2 -178.88(18) . . . . ?
C8 C9 N3 C14 176.36(19) . . . . ?
C10 C9 N3 C14 -3.2(3) . . . . ?
C15 C14 N3 N2 -35.2(2) . . . . ?
C15 C14 N3 C9 149.41(19) . . . . ?
C21 B1 N4 Fe1 -77.12(17) . . . . ?
C17 B1 N4 Fe1 168.83(12) . . . . ?
C16 B1 N4 Fe1 47.25(18) . . . . ?

_refine_diff_density_max         0.599
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.054


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_EN151_2_0m
_database_code_depnum_ccdc_archive 'CCDC 1941371'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller '
;Purdue University
United States of America
;
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H40 B Br2 Fe N5'
_chemical_formula_weight         625.09

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   33.5193(8)
_cell_length_b                   12.4500(3)
_cell_length_c                   13.6964(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.8345(9)
_cell_angle_gamma                90
_cell_volume                     5686.1(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9792
_cell_measurement_theta_min      2.6502
_cell_measurement_theta_max      80.5095

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_F_000             2560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    7.695
_shelx_estimated_absorpt_T_min   0.133
_shelx_estimated_absorpt_T_max   0.748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5374
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37322
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.650
_diffrn_reflns_theta_max         80.537
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6111
_reflns_number_gt                5668
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Apex3 v2017.3-0 (Bruker, 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev937 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Terminal amine H atom positions were refined and N-H distances were 
restrained to 0.91(2) Angstrom.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0361P)²+3.3750P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6111
_refine_ls_number_parameters     308
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0257
_refine_ls_wR_factor_ref         0.0694
_refine_ls_wR_factor_gt          0.0679
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000

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 0.33256(2) 0.64052(2) 0.63550(2) 0.03787(7) Uani 1 1 d . . . . .
Br2 Br 0.27627(2) 0.39776(2) 0.77358(2) 0.02773(6) Uani 1 1 d . . . . .
Fe1 Fe 0.29613(2) 0.47620(2) 0.62530(2) 0.02280(7) Uani 1 1 d . . . . .
N1 N 0.24834(4) 0.47050(11) 0.51151(11) 0.0226(3) Uani 1 1 d . . . . .
N2 N 0.31706(4) 0.36540(11) 0.53082(10) 0.0213(3) Uani 1 1 d . . . . .
N3 N 0.35136(4) 0.31186(11) 0.52044(10) 0.0213(3) Uani 1 1 d . . . . .
N4 N 0.37489(5) 0.37692(12) 0.90714(11) 0.0252(3) Uani 1 1 d . . . . .
H4A H 0.354748 0.343161 0.869429 0.030 Uiso 1 1 calc R U . . .
H4B H 0.372401 0.359891 0.970846 0.030 Uiso 1 1 calc R U . . .
N5 N 0.36975(6) 0.49223(13) 0.89497(13) 0.0331(4) Uani 1 1 d D . . . .
H5A H 0.3846(7) 0.507(2) 0.8461(16) 0.040 Uiso 1 1 d D U . . .
H5B H 0.3435(5) 0.504(2) 0.8751(19) 0.040 Uiso 1 1 d D U . . .
C1 C 0.21315(7) 0.62184(18) 0.57561(17) 0.0397(5) Uani 1 1 d . . . . .
H1A H 0.217517 0.591871 0.641997 0.060 Uiso 1 1 calc R U . . .
H1B H 0.186550 0.655149 0.566031 0.060 Uiso 1 1 calc R U . . .
H1C H 0.233696 0.676054 0.566998 0.060 Uiso 1 1 calc R U . . .
C2 C 0.21572(6) 0.53388(14) 0.50195(14) 0.0271(4) Uani 1 1 d . . . . .
C3 C 0.18564(6) 0.51846(15) 0.42547(15) 0.0299(4) Uani 1 1 d . . . . .
H3 H 0.163165 0.565319 0.418025 0.036 Uiso 1 1 calc R U . . .
C4 C 0.18859(5) 0.43456(15) 0.36029(14) 0.0287(4) Uani 1 1 d . . . . .
H4 H 0.167668 0.421664 0.309484 0.034 Uiso 1 1 calc R U . . .
C5 C 0.22225(5) 0.36963(14) 0.36973(13) 0.0243(3) Uani 1 1 d . . . . .
H5 H 0.224865 0.311533 0.325865 0.029 Uiso 1 1 calc R U . . .
C6 C 0.25206(5) 0.39145(13) 0.44478(13) 0.0215(3) Uani 1 1 d . . . . .
C7 C 0.29082(5) 0.33580(13) 0.45542(12) 0.0209(3) Uani 1 1 d . . . . .
C8 C 0.30834(5) 0.26240(13) 0.39635(12) 0.0224(3) Uani 1 1 d . . . . .
H8 H 0.296132 0.228374 0.338810 0.027 Uiso 1 1 calc R U . . .
C9 C 0.34752(5) 0.24911(13) 0.43905(12) 0.0215(3) Uani 1 1 d . . . . .
C10 C 0.38105(5) 0.18291(14) 0.40215(13) 0.0259(3) Uani 1 1 d . . . . .
C11 C 0.36277(7) 0.11160(17) 0.31749(17) 0.0378(5) Uani 1 1 d . . . . .
H11A H 0.342367 0.064605 0.341149 0.057 Uiso 1 1 calc R U . . .
H11B H 0.383903 0.067737 0.293016 0.057 Uiso 1 1 calc R U . . .
H11C H 0.350403 0.157016 0.264323 0.057 Uiso 1 1 calc R U . . .
C12 C 0.41233(6) 0.25654(16) 0.36197(14) 0.0307(4) Uani 1 1 d . . . . .
H12A H 0.423554 0.305112 0.413996 0.046 Uiso 1 1 calc R U . . .
H12B H 0.399531 0.298720 0.307035 0.046 Uiso 1 1 calc R U . . .
H12C H 0.433862 0.212762 0.339259 0.046 Uiso 1 1 calc R U . . .
C13 C 0.40108(6) 0.10891(16) 0.48235(16) 0.0334(4) Uani 1 1 d . . . . .
H13A H 0.380887 0.061129 0.505891 0.050 Uiso 1 1 calc R U . . .
H13B H 0.413299 0.152462 0.537038 0.050 Uiso 1 1 calc R U . . .
H13C H 0.421841 0.065906 0.455321 0.050 Uiso 1 1 calc R U . . .
C14 C 0.38651(5) 0.34233(14) 0.58784(13) 0.0238(3) Uani 1 1 d . . . . .
H14A H 0.388843 0.421600 0.588659 0.029 Uiso 1 1 calc R U . . .
H14B H 0.410895 0.313094 0.562406 0.029 Uiso 1 1 calc R U . . .
C15 C 0.38494(5) 0.30298(14) 0.69216(12) 0.0247(3) Uani 1 1 d . . . . .
H15A H 0.387888 0.223869 0.694086 0.030 Uiso 1 1 calc R U . . .
H15B H 0.358591 0.321262 0.714446 0.030 Uiso 1 1 calc R U . . .
C16 C 0.41839(5) 0.35426(14) 0.76128(13) 0.0243(3) Uani 1 1 d . . . . .
H16A H 0.417085 0.433025 0.751532 0.029 Uiso 1 1 calc R U . . .
H16B H 0.444430 0.329664 0.741210 0.029 Uiso 1 1 calc R U . . .
C17 C 0.42023(6) 0.20416(14) 0.90950(14) 0.0273(4) Uani 1 1 d . . . . .
H17 H 0.397169 0.165655 0.872895 0.033 Uiso 1 1 calc R U . . .
C18 C 0.45956(6) 0.15900(16) 0.87636(15) 0.0329(4) Uani 1 1 d . . . . .
H18A H 0.462507 0.083450 0.898475 0.040 Uiso 1 1 calc R U . . .
H18B H 0.457380 0.158914 0.803736 0.040 Uiso 1 1 calc R U . . .
C19 C 0.49773(6) 0.22100(18) 0.91482(16) 0.0367(4) Uani 1 1 d . . . . .
H19A H 0.506005 0.197056 0.982790 0.044 Uiso 1 1 calc R U . . .
H19B H 0.519422 0.200985 0.874342 0.044 Uiso 1 1 calc R U . . .
C20 C 0.49409(6) 0.34408(17) 0.91490(15) 0.0322(4) Uani 1 1 d . . . . .
H20A H 0.497596 0.370588 0.848157 0.039 Uiso 1 1 calc R U . . .
H20B H 0.516384 0.373532 0.959973 0.039 Uiso 1 1 calc R U . . .
C21 C 0.45440(6) 0.38918(15) 0.94525(13) 0.0266(4) Uani 1 1 d . . . . .
H21 H 0.453334 0.467660 0.929660 0.032 Uiso 1 1 calc R U . . .
C22 C 0.45007(6) 0.37566(16) 1.05500(14) 0.0314(4) Uani 1 1 d . . . . .
H22A H 0.426003 0.415594 1.070787 0.038 Uiso 1 1 calc R U . . .
H22B H 0.473651 0.408594 1.092975 0.038 Uiso 1 1 calc R U . . .
C23 C 0.44642(7) 0.25885(17) 1.08850(14) 0.0359(4) Uani 1 1 d . . . . .
H23A H 0.437244 0.258575 1.154963 0.043 Uiso 1 1 calc R U . . .
H23B H 0.473328 0.225329 1.093385 0.043 Uiso 1 1 calc R U . . .
C24 C 0.41747(6) 0.18987(15) 1.02040(15) 0.0335(4) Uani 1 1 d . . . . .
H24A H 0.389710 0.206639 1.034110 0.040 Uiso 1 1 calc R U . . .
H24B H 0.422481 0.113385 1.037203 0.040 Uiso 1 1 calc R U . . .
B1 B 0.41806(6) 0.33022(16) 0.87797(15) 0.0235(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
Br1 Fe1 2.3794(3) . ?
Br2 Fe1 2.4075(3) . ?
Fe1 N2 2.0627(14) . ?
Fe1 N1 2.1195(15) . ?
N1 C2 1.344(2) . ?
N1 C6 1.357(2) . ?
N2 C7 1.339(2) . ?
N2 N3 1.349(2) . ?
N3 C9 1.357(2) . ?
N3 C14 1.471(2) . ?
N4 N5 1.453(2) . ?
N4 B1 1.646(2) . ?
N4 H4A 0.9100 . ?
N4 H4B 0.9100 . ?
N5 H5A 0.892(17) . ?
N5 H5B 0.906(17) . ?
C1 C2 1.497(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.392(3) . ?
C3 C4 1.384(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.466(2) . ?
C7 C8 1.390(2) . ?
C8 C9 1.392(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.521(2) . ?
C10 C13 1.535(3) . ?
C10 C12 1.536(3) . ?
C10 C11 1.537(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.516(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.531(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 B1 1.627(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C24 1.541(3) . ?
C17 C18 1.543(3) . ?
C17 B1 1.627(3) . ?
C17 H17 1.0000 . ?
C18 C19 1.541(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.537(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.540(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.534(3) . ?
C21 B1 1.626(3) . ?
C21 H21 1.0000 . ?
C22 C23 1.534(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.538(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?

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
N2 Fe1 N1 78.24(6) . . ?
N2 Fe1 Br1 113.99(4) . . ?
N1 Fe1 Br1 114.64(4) . . ?
N2 Fe1 Br2 113.50(4) . . ?
N1 Fe1 Br2 110.71(4) . . ?
Br1 Fe1 Br2 118.916(13) . . ?
C2 N1 C6 119.31(15) . . ?
C2 N1 Fe1 126.77(12) . . ?
C6 N1 Fe1 113.90(11) . . ?
C7 N2 N3 106.44(13) . . ?
C7 N2 Fe1 115.43(11) . . ?
N3 N2 Fe1 138.12(11) . . ?
N2 N3 C9 111.13(13) . . ?
N2 N3 C14 116.31(13) . . ?
C9 N3 C14 131.87(14) . . ?
N5 N4 B1 114.70(14) . . ?
N5 N4 H4A 108.6 . . ?
B1 N4 H4A 108.6 . . ?
N5 N4 H4B 108.6 . . ?
B1 N4 H4B 108.6 . . ?
H4A N4 H4B 107.6 . . ?
N4 N5 H5A 102.9(17) . . ?
N4 N5 H5B 107.0(17) . . ?
H5A N5 H5B 110(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 120.83(17) . . ?
N1 C2 C1 117.76(17) . . ?
C3 C2 C1 121.40(17) . . ?
C4 C3 C2 119.72(17) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 119.46(17) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 118.34(17) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
N1 C6 C5 122.20(16) . . ?
N1 C6 C7 114.63(15) . . ?
C5 C6 C7 123.08(16) . . ?
N2 C7 C8 110.28(15) . . ?
N2 C7 C6 116.92(15) . . ?
C8 C7 C6 132.50(16) . . ?
C7 C8 C9 105.68(15) . . ?
C7 C8 H8 127.2 . . ?
C9 C8 H8 127.2 . . ?
N3 C9 C8 106.47(14) . . ?
N3 C9 C10 124.99(15) . . ?
C8 C9 C10 128.48(15) . . ?
C9 C10 C13 111.82(15) . . ?
C9 C10 C12 110.49(14) . . ?
C13 C10 C12 110.47(15) . . ?
C9 C10 C11 108.19(15) . . ?
C13 C10 C11 107.76(16) . . ?
C12 C10 C11 107.97(16) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C15 113.95(14) . . ?
N3 C14 H14A 108.8 . . ?
C15 C14 H14A 108.8 . . ?
N3 C14 H14B 108.8 . . ?
C15 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 C16 110.77(14) . . ?
C14 C15 H15A 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C15 C16 B1 116.93(14) . . ?
C15 C16 H16A 108.1 . . ?
B1 C16 H16A 108.1 . . ?
C15 C16 H16B 108.1 . . ?
B1 C16 H16B 108.1 . . ?
H16A C16 H16B 107.3 . . ?
C24 C17 C18 112.73(16) . . ?
C24 C17 B1 111.54(15) . . ?
C18 C17 B1 106.86(15) . . ?
C24 C17 H17 108.5 . . ?
C18 C17 H17 108.5 . . ?
B1 C17 H17 108.5 . . ?
C19 C18 C17 114.93(16) . . ?
C19 C18 H18A 108.5 . . ?
C17 C18 H18A 108.5 . . ?
C19 C18 H18B 108.5 . . ?
C17 C18 H18B 108.5 . . ?
H18A C18 H18B 107.5 . . ?
C20 C19 C18 115.89(16) . . ?
C20 C19 H19A 108.3 . . ?
C18 C19 H19A 108.3 . . ?
C20 C19 H19B 108.3 . . ?
C18 C19 H19B 108.3 . . ?
H19A C19 H19B 107.4 . . ?
C19 C20 C21 115.75(16) . . ?
C19 C20 H20A 108.3 . . ?
C21 C20 H20A 108.3 . . ?
C19 C20 H20B 108.3 . . ?
C21 C20 H20B 108.3 . . ?
H20A C20 H20B 107.4 . . ?
C22 C21 C20 113.27(16) . . ?
C22 C21 B1 111.45(15) . . ?
C20 C21 B1 107.49(14) . . ?
C22 C21 H21 108.2 . . ?
C20 C21 H21 108.2 . . ?
B1 C21 H21 108.2 . . ?
C21 C22 C23 114.56(16) . . ?
C21 C22 H22A 108.6 . . ?
C23 C22 H22A 108.6 . . ?
C21 C22 H22B 108.6 . . ?
C23 C22 H22B 108.6 . . ?
H22A C22 H22B 107.6 . . ?
C22 C23 C24 114.37(16) . . ?
C22 C23 H23A 108.7 . . ?
C24 C23 H23A 108.7 . . ?
C22 C23 H23B 108.7 . . ?
C24 C23 H23B 108.7 . . ?
H23A C23 H23B 107.6 . . ?
C23 C24 C17 115.83(16) . . ?
C23 C24 H24A 108.3 . . ?
C17 C24 H24A 108.3 . . ?
C23 C24 H24B 108.3 . . ?
C17 C24 H24B 108.3 . . ?
H24A C24 H24B 107.4 . . ?
C21 B1 C16 113.21(14) . . ?
C21 B1 C17 105.92(15) . . ?
C16 B1 C17 115.69(15) . . ?
C21 B1 N4 109.24(14) . . ?
C16 B1 N4 105.51(14) . . ?
C17 B1 N4 107.04(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N2 N3 C9 0.49(18) . . . . ?
Fe1 N2 N3 C9 -178.15(13) . . . . ?
C7 N2 N3 C14 172.12(14) . . . . ?
Fe1 N2 N3 C14 -6.5(2) . . . . ?
C6 N1 C2 C3 0.9(3) . . . . ?
Fe1 N1 C2 C3 -177.25(13) . . . . ?
C6 N1 C2 C1 -178.58(17) . . . . ?
Fe1 N1 C2 C1 3.3(2) . . . . ?
N1 C2 C3 C4 2.3(3) . . . . ?
C1 C2 C3 C4 -178.34(19) . . . . ?
C2 C3 C4 C5 -2.6(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C2 N1 C6 C5 -3.7(2) . . . . ?
Fe1 N1 C6 C5 174.65(13) . . . . ?
C2 N1 C6 C7 173.04(15) . . . . ?
Fe1 N1 C6 C7 -8.61(17) . . . . ?
C4 C5 C6 N1 3.3(3) . . . . ?
C4 C5 C6 C7 -173.15(16) . . . . ?
N3 N2 C7 C8 0.21(18) . . . . ?
Fe1 N2 C7 C8 179.21(11) . . . . ?
N3 N2 C7 C6 -174.19(13) . . . . ?
Fe1 N2 C7 C6 4.80(18) . . . . ?
N1 C6 C7 N2 2.7(2) . . . . ?
C5 C6 C7 N2 179.43(16) . . . . ?
N1 C6 C7 C8 -170.14(17) . . . . ?
C5 C6 C7 C8 6.6(3) . . . . ?
N2 C7 C8 C9 -0.80(19) . . . . ?
C6 C7 C8 C9 172.43(17) . . . . ?
N2 N3 C9 C8 -0.99(18) . . . . ?
C14 N3 C9 C8 -170.89(16) . . . . ?
N2 N3 C9 C10 176.35(15) . . . . ?
C14 N3 C9 C10 6.4(3) . . . . ?
C7 C8 C9 N3 1.06(18) . . . . ?
C7 C8 C9 C10 -176.15(16) . . . . ?
N3 C9 C10 C13 53.4(2) . . . . ?
C8 C9 C10 C13 -129.88(19) . . . . ?
N3 C9 C10 C12 -70.1(2) . . . . ?
C8 C9 C10 C12 106.6(2) . . . . ?
N3 C9 C10 C11 171.90(17) . . . . ?
C8 C9 C10 C11 -11.4(3) . . . . ?
N2 N3 C14 C15 73.62(19) . . . . ?
C9 N3 C14 C15 -116.89(19) . . . . ?
N3 C14 C15 C16 -169.82(14) . . . . ?
C14 C15 C16 B1 173.74(15) . . . . ?
C24 C17 C18 C19 -68.2(2) . . . . ?
B1 C17 C18 C19 54.7(2) . . . . ?
C17 C18 C19 C20 -40.8(3) . . . . ?
C18 C19 C20 C21 39.5(2) . . . . ?
C19 C20 C21 C22 71.3(2) . . . . ?
C19 C20 C21 B1 -52.2(2) . . . . ?
C20 C21 C22 C23 -66.6(2) . . . . ?
B1 C21 C22 C23 54.8(2) . . . . ?
C21 C22 C23 C24 -44.8(2) . . . . ?
C22 C23 C24 C17 43.1(2) . . . . ?
C18 C17 C24 C23 69.4(2) . . . . ?
B1 C17 C24 C23 -50.8(2) . . . . ?
C22 C21 B1 C16 173.14(15) . . . . ?
C20 C21 B1 C16 -62.19(19) . . . . ?
C22 C21 B1 C17 -59.08(19) . . . . ?
C20 C21 B1 C17 65.59(18) . . . . ?
C22 C21 B1 N4 55.91(19) . . . . ?
C20 C21 B1 N4 -179.43(14) . . . . ?
C15 C16 B1 C21 -179.36(15) . . . . ?
C15 C16 B1 C17 58.1(2) . . . . ?
C15 C16 B1 N4 -59.95(19) . . . . ?
C24 C17 B1 C21 56.75(19) . . . . ?
C18 C17 B1 C21 -66.87(18) . . . . ?
C24 C17 B1 C16 -176.96(15) . . . . ?
C18 C17 B1 C16 59.4(2) . . . . ?
C24 C17 B1 N4 -59.72(19) . . . . ?
C18 C17 B1 N4 176.66(14) . . . . ?
N5 N4 B1 C21 58.71(19) . . . . ?
N5 N4 B1 C16 -63.29(18) . . . . ?
N5 N4 B1 C17 172.97(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N4 H4A Br2 0.91 2.90 3.6207(16) 137.3 . yes
N4 H4B Br1 0.91 2.74 3.5700(15) 153.0 6_566 yes
N5 H5B Br2 0.906(17) 2.85(2) 3.5925(19) 140(2) . yes

_refine_diff_density_max         0.565
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.058


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_JK5101_2_0m
_database_code_depnum_ccdc_archive 'CCDC 1941375'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller '
;Purdue University
United States of America
;
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H39 B Br2 N4 O Zn'
_chemical_formula_weight         635.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   33.438(3)
_cell_length_b                   12.3550(8)
_cell_length_c                   13.6531(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.908(3)
_cell_angle_gamma                90
_cell_volume                     5610.5(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9910
_cell_measurement_theta_min      2.4683
_cell_measurement_theta_max      28.3306

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_F_000             2592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    3.747
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4815
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            40403
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.352
_diffrn_reflns_theta_max         28.369
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.890
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.890
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             6257
_reflns_number_gt                4832
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Apex3 v2018.1-0 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev946 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0570P)²+12.3301P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00040(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6257
_refine_ls_number_parameters     305
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1123
_refine_ls_wR_factor_gt          0.1032
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.22164(2) 0.40810(3) 0.23075(2) 0.03090(12) Uani 1 1 d . . . . .
Br2 Br 0.17233(2) 0.64770(3) 0.37632(3) 0.04371(14) Uani 1 1 d . . . . .
Zn3 Zn 0.20556(2) 0.48043(3) 0.38324(3) 0.02684(13) Uani 1 1 d . . . . .
O1 O 0.13264(9) 0.4900(2) 0.1076(2) 0.0445(7) Uani 1 1 d . . . . .
H1 H 0.155346 0.501864 0.138082 0.067 Uiso 1 1 calc R U . . .
N1 N 0.25380(8) 0.4680(2) 0.48995(18) 0.0255(6) Uani 1 1 d . . . . .
N2 N 0.18340(8) 0.3695(2) 0.47284(18) 0.0250(6) Uani 1 1 d . . . . .
N3 N 0.14824(8) 0.3196(2) 0.48433(18) 0.0248(6) Uani 1 1 d . . . . .
N4 N 0.12691(9) 0.3760(3) 0.0952(2) 0.0302(7) Uani 1 1 d . . . . .
H4A H 0.146895 0.340814 0.132803 0.036 Uiso 1 1 calc R U . . .
H4B H 0.129052 0.358692 0.031193 0.036 Uiso 1 1 calc R U . . .
C1 C 0.29076(13) 0.6149(3) 0.4226(3) 0.0412(9) Uani 1 1 d . . . . .
H1A H 0.283274 0.585414 0.356612 0.062 Uiso 1 1 calc R U . . .
H1B H 0.318485 0.641570 0.427123 0.062 Uiso 1 1 calc R U . . .
H1C H 0.272642 0.674598 0.434895 0.062 Uiso 1 1 calc R U . . .
C2 C 0.28750(11) 0.5278(3) 0.4978(2) 0.0307(8) Uani 1 1 d . . . . .
C3 C 0.31763(11) 0.5102(3) 0.5739(3) 0.0349(8) Uani 1 1 d . . . . .
H3 H 0.340938 0.554631 0.580303 0.042 Uiso 1 1 calc R U . . .
C4 C 0.31349(11) 0.4277(3) 0.6400(2) 0.0328(8) Uani 1 1 d . . . . .
H4 H 0.334404 0.413350 0.690881 0.039 Uiso 1 1 calc R U . . .
C5 C 0.27894(11) 0.3660(3) 0.6323(2) 0.0288(7) Uani 1 1 d . . . . .
H5 H 0.275703 0.308608 0.677104 0.035 Uiso 1 1 calc R U . . .
C6 C 0.24909(10) 0.3901(3) 0.5575(2) 0.0233(7) Uani 1 1 d . . . . .
C7 C 0.20959(10) 0.3375(3) 0.5477(2) 0.0241(7) Uani 1 1 d . . . . .
C8 C 0.19113(11) 0.2658(3) 0.6082(2) 0.0262(7) Uani 1 1 d . . . . .
H8 H 0.203128 0.231045 0.666002 0.031 Uiso 1 1 calc R U . . .
C9 C 0.15170(10) 0.2557(3) 0.5665(2) 0.0253(7) Uani 1 1 d . . . . .
C10 C 0.11726(11) 0.1936(3) 0.6044(2) 0.0292(8) Uani 1 1 d . . . . .
C11 C 0.13432(13) 0.1210(3) 0.6891(3) 0.0400(9) Uani 1 1 d . . . . .
H11A H 0.153723 0.070353 0.665417 0.060 Uiso 1 1 calc R U . . .
H11B H 0.112408 0.080349 0.714390 0.060 Uiso 1 1 calc R U . . .
H11C H 0.147779 0.165721 0.741903 0.060 Uiso 1 1 calc R U . . .
C12 C 0.08699(12) 0.2728(3) 0.6432(2) 0.0374(9) Uani 1 1 d . . . . .
H12A H 0.076654 0.321925 0.590240 0.056 Uiso 1 1 calc R U . . .
H12B H 0.100413 0.314814 0.697952 0.056 Uiso 1 1 calc R U . . .
H12C H 0.064637 0.231908 0.666246 0.056 Uiso 1 1 calc R U . . .
C13 C 0.09611(13) 0.1204(4) 0.5240(3) 0.0403(9) Uani 1 1 d . . . . .
H13A H 0.084822 0.165022 0.468576 0.061 Uiso 1 1 calc R U . . .
H13B H 0.074454 0.080328 0.550974 0.061 Uiso 1 1 calc R U . . .
H13C H 0.115580 0.069319 0.501322 0.061 Uiso 1 1 calc R U . . .
C14 C 0.11362(10) 0.3520(3) 0.4156(2) 0.0280(7) Uani 1 1 d . . . . .
H14A H 0.112511 0.432037 0.412503 0.034 Uiso 1 1 calc R U . . .
H14B H 0.088679 0.326527 0.441478 0.034 Uiso 1 1 calc R U . . .
C15 C 0.11484(10) 0.3081(3) 0.3124(2) 0.0269(7) Uani 1 1 d . . . . .
H15A H 0.109564 0.229276 0.312175 0.032 Uiso 1 1 calc R U . . .
H15B H 0.141933 0.319799 0.291158 0.032 Uiso 1 1 calc R U . . .
C16 C 0.08355(11) 0.3641(3) 0.2407(2) 0.0282(7) Uani 1 1 d . . . . .
H16A H 0.087533 0.443251 0.247519 0.034 Uiso 1 1 calc R U . . .
H16B H 0.056613 0.347371 0.260837 0.034 Uiso 1 1 calc R U . . .
C17 C 0.08149(12) 0.2054(3) 0.0985(2) 0.0321(8) Uani 1 1 d . . . . .
H17 H 0.104496 0.168014 0.137162 0.038 Uiso 1 1 calc R U . . .
C18 C 0.04189(13) 0.1621(3) 0.1327(3) 0.0402(9) Uani 1 1 d . . . . .
H18A H 0.043807 0.165631 0.205437 0.048 Uiso 1 1 calc R U . . .
H18B H 0.038894 0.085051 0.113477 0.048 Uiso 1 1 calc R U . . .
C19 C 0.00378(12) 0.2239(4) 0.0904(3) 0.0453(10) Uani 1 1 d . . . . .
H19A H -0.004383 0.196299 0.023209 0.054 Uiso 1 1 calc R U . . .
H19B H -0.018168 0.206760 0.131287 0.054 Uiso 1 1 calc R U . . .
C20 C 0.00775(11) 0.3467(3) 0.0849(3) 0.0388(9) Uani 1 1 d . . . . .
H20A H 0.003800 0.377082 0.150253 0.047 Uiso 1 1 calc R U . . .
H20B H -0.014300 0.374319 0.037515 0.047 Uiso 1 1 calc R U . . .
C21 C 0.04773(11) 0.3902(3) 0.0543(2) 0.0328(8) Uani 1 1 d . . . . .
H21 H 0.048851 0.469963 0.066552 0.039 Uiso 1 1 calc R U . . .
C22 C 0.05218(12) 0.3697(3) -0.0554(2) 0.0362(9) Uani 1 1 d . . . . .
H22A H 0.028589 0.401075 -0.095256 0.043 Uiso 1 1 calc R U . . .
H22B H 0.076343 0.408540 -0.072954 0.043 Uiso 1 1 calc R U . . .
C23 C 0.05580(13) 0.2508(3) -0.0836(2) 0.0403(9) Uani 1 1 d . . . . .
H23A H 0.065130 0.246720 -0.149984 0.048 Uiso 1 1 calc R U . . .
H23B H 0.028783 0.217306 -0.087418 0.048 Uiso 1 1 calc R U . . .
C24 C 0.08445(13) 0.1848(3) -0.0124(3) 0.0374(9) Uani 1 1 d . . . . .
H24A H 0.112332 0.200322 -0.026447 0.045 Uiso 1 1 calc R U . . .
H24B H 0.079345 0.107033 -0.025874 0.045 Uiso 1 1 calc R U . . .
B1 B 0.08361(12) 0.3328(4) 0.1250(3) 0.0279(8) 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 Zn3 2.3775(5) . ?
Br2 Zn3 2.3437(6) . ?
Zn3 N2 2.028(3) . ?
Zn3 N1 2.065(3) . ?
O1 N4 1.430(4) . ?
O1 H1 0.8400 . ?
N1 C2 1.343(5) . ?
N1 C6 1.353(4) . ?
N2 C7 1.335(4) . ?
N2 N3 1.350(4) . ?
N3 C9 1.367(4) . ?
N3 C14 1.469(4) . ?
N4 B1 1.633(5) . ?
N4 H4A 0.9100 . ?
N4 H4B 0.9100 . ?
C1 C2 1.498(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.388(5) . ?
C3 C4 1.378(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.465(5) . ?
C7 C8 1.398(5) . ?
C8 C9 1.387(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.518(5) . ?
C10 C11 1.527(5) . ?
C10 C13 1.537(5) . ?
C10 C12 1.540(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.514(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.523(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 B1 1.627(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.544(5) . ?
C17 C24 1.548(5) . ?
C17 B1 1.616(6) . ?
C17 H17 1.0000 . ?
C18 C19 1.545(6) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.525(6) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.537(5) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.542(5) . ?
C21 B1 1.623(5) . ?
C21 H21 1.0000 . ?
C22 C23 1.527(6) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.528(6) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?

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
N2 Zn3 N1 80.30(11) . . ?
N2 Zn3 Br2 114.79(8) . . ?
N1 Zn3 Br2 115.25(8) . . ?
N2 Zn3 Br1 113.82(8) . . ?
N1 Zn3 Br1 111.06(8) . . ?
Br2 Zn3 Br1 116.430(19) . . ?
N4 O1 H1 109.5 . . ?
C2 N1 C6 119.5(3) . . ?
C2 N1 Zn3 127.1(2) . . ?
C6 N1 Zn3 113.3(2) . . ?
C7 N2 N3 106.7(3) . . ?
C7 N2 Zn3 114.2(2) . . ?
N3 N2 Zn3 139.0(2) . . ?
N2 N3 C9 110.9(3) . . ?
N2 N3 C14 116.1(3) . . ?
C9 N3 C14 132.5(3) . . ?
O1 N4 B1 113.8(3) . . ?
O1 N4 H4A 108.8 . . ?
B1 N4 H4A 108.8 . . ?
O1 N4 H4B 108.8 . . ?
B1 N4 H4B 108.8 . . ?
H4A N4 H4B 107.7 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 120.8(3) . . ?
N1 C2 C1 117.4(3) . . ?
C3 C2 C1 121.8(3) . . ?
C4 C3 C2 119.5(4) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 119.9(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 118.2(3) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
N1 C6 C5 122.0(3) . . ?
N1 C6 C7 114.8(3) . . ?
C5 C6 C7 123.1(3) . . ?
N2 C7 C8 110.2(3) . . ?
N2 C7 C6 116.9(3) . . ?
C8 C7 C6 132.5(3) . . ?
C9 C8 C7 105.8(3) . . ?
C9 C8 H8 127.1 . . ?
C7 C8 H8 127.1 . . ?
N3 C9 C8 106.4(3) . . ?
N3 C9 C10 124.6(3) . . ?
C8 C9 C10 128.9(3) . . ?
C9 C10 C11 108.5(3) . . ?
C9 C10 C13 111.3(3) . . ?
C11 C10 C13 107.7(3) . . ?
C9 C10 C12 110.2(3) . . ?
C11 C10 C12 108.6(3) . . ?
C13 C10 C12 110.4(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C15 113.7(3) . . ?
N3 C14 H14A 108.8 . . ?
C15 C14 H14A 108.8 . . ?
N3 C14 H14B 108.8 . . ?
C15 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 C16 110.6(3) . . ?
C14 C15 H15A 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C15 C16 B1 116.6(3) . . ?
C15 C16 H16A 108.2 . . ?
B1 C16 H16A 108.2 . . ?
C15 C16 H16B 108.2 . . ?
B1 C16 H16B 108.2 . . ?
H16A C16 H16B 107.3 . . ?
C18 C17 C24 112.5(3) . . ?
C18 C17 B1 106.8(3) . . ?
C24 C17 B1 111.9(3) . . ?
C18 C17 H17 108.5 . . ?
C24 C17 H17 108.5 . . ?
B1 C17 H17 108.5 . . ?
C17 C18 C19 114.6(3) . . ?
C17 C18 H18A 108.6 . . ?
C19 C18 H18A 108.6 . . ?
C17 C18 H18B 108.6 . . ?
C19 C18 H18B 108.6 . . ?
H18A C18 H18B 107.6 . . ?
C20 C19 C18 115.9(3) . . ?
C20 C19 H19A 108.3 . . ?
C18 C19 H19A 108.3 . . ?
C20 C19 H19B 108.3 . . ?
C18 C19 H19B 108.3 . . ?
H19A C19 H19B 107.4 . . ?
C19 C20 C21 116.3(3) . . ?
C19 C20 H20A 108.2 . . ?
C21 C20 H20A 108.2 . . ?
C19 C20 H20B 108.2 . . ?
C21 C20 H20B 108.2 . . ?
H20A C20 H20B 107.4 . . ?
C20 C21 C22 112.3(3) . . ?
C20 C21 B1 107.2(3) . . ?
C22 C21 B1 111.5(3) . . ?
C20 C21 H21 108.6 . . ?
C22 C21 H21 108.6 . . ?
B1 C21 H21 108.6 . . ?
C23 C22 C21 114.9(3) . . ?
C23 C22 H22A 108.5 . . ?
C21 C22 H22A 108.5 . . ?
C23 C22 H22B 108.5 . . ?
C21 C22 H22B 108.5 . . ?
H22A C22 H22B 107.5 . . ?
C22 C23 C24 114.4(3) . . ?
C22 C23 H23A 108.6 . . ?
C24 C23 H23A 108.6 . . ?
C22 C23 H23B 108.6 . . ?
C24 C23 H23B 108.6 . . ?
H23A C23 H23B 107.6 . . ?
C23 C24 C17 115.8(3) . . ?
C23 C24 H24A 108.3 . . ?
C17 C24 H24A 108.3 . . ?
C23 C24 H24B 108.3 . . ?
C17 C24 H24B 108.3 . . ?
H24A C24 H24B 107.4 . . ?
C17 B1 C21 106.2(3) . . ?
C17 B1 C16 116.4(3) . . ?
C21 B1 C16 113.5(3) . . ?
C17 B1 N4 106.4(3) . . ?
C21 B1 N4 109.2(3) . . ?
C16 B1 N4 104.7(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N2 N3 C9 0.1(4) . . . . ?
Zn3 N2 N3 C9 -175.3(3) . . . . ?
C7 N2 N3 C14 173.7(3) . . . . ?
Zn3 N2 N3 C14 -1.6(5) . . . . ?
C6 N1 C2 C3 0.4(5) . . . . ?
Zn3 N1 C2 C3 -179.9(3) . . . . ?
C6 N1 C2 C1 -178.5(3) . . . . ?
Zn3 N1 C2 C1 1.2(5) . . . . ?
N1 C2 C3 C4 2.4(5) . . . . ?
C1 C2 C3 C4 -178.8(4) . . . . ?
C2 C3 C4 C5 -2.3(5) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C2 N1 C6 C5 -3.3(5) . . . . ?
Zn3 N1 C6 C5 177.0(2) . . . . ?
C2 N1 C6 C7 174.0(3) . . . . ?
Zn3 N1 C6 C7 -5.7(3) . . . . ?
C4 C5 C6 N1 3.3(5) . . . . ?
C4 C5 C6 C7 -173.8(3) . . . . ?
N3 N2 C7 C8 0.2(4) . . . . ?
Zn3 N2 C7 C8 176.9(2) . . . . ?
N3 N2 C7 C6 -173.6(3) . . . . ?
Zn3 N2 C7 C6 3.1(4) . . . . ?
N1 C6 C7 N2 1.8(4) . . . . ?
C5 C6 C7 N2 179.1(3) . . . . ?
N1 C6 C7 C8 -170.2(3) . . . . ?
C5 C6 C7 C8 7.0(6) . . . . ?
N2 C7 C8 C9 -0.4(4) . . . . ?
C6 C7 C8 C9 172.1(3) . . . . ?
N2 N3 C9 C8 -0.3(4) . . . . ?
C14 N3 C9 C8 -172.5(3) . . . . ?
N2 N3 C9 C10 176.2(3) . . . . ?
C14 N3 C9 C10 3.9(6) . . . . ?
C7 C8 C9 N3 0.4(4) . . . . ?
C7 C8 C9 C10 -175.9(3) . . . . ?
N3 C9 C10 C11 172.7(3) . . . . ?
C8 C9 C10 C11 -11.6(5) . . . . ?
N3 C9 C10 C13 54.4(5) . . . . ?
C8 C9 C10 C13 -130.0(4) . . . . ?
N3 C9 C10 C12 -68.5(4) . . . . ?
C8 C9 C10 C12 107.2(4) . . . . ?
N2 N3 C14 C15 73.9(4) . . . . ?
C9 N3 C14 C15 -114.2(4) . . . . ?
N3 C14 C15 C16 -167.5(3) . . . . ?
C14 C15 C16 B1 175.1(3) . . . . ?
C24 C17 C18 C19 -68.4(4) . . . . ?
B1 C17 C18 C19 54.8(4) . . . . ?
C17 C18 C19 C20 -40.4(5) . . . . ?
C18 C19 C20 C21 39.0(5) . . . . ?
C19 C20 C21 C22 71.3(4) . . . . ?
C19 C20 C21 B1 -51.6(4) . . . . ?
C20 C21 C22 C23 -66.5(4) . . . . ?
B1 C21 C22 C23 53.9(5) . . . . ?
C21 C22 C23 C24 -44.6(5) . . . . ?
C22 C23 C24 C17 43.0(5) . . . . ?
C18 C17 C24 C23 69.6(5) . . . . ?
B1 C17 C24 C23 -50.6(5) . . . . ?
C18 C17 B1 C21 -67.3(3) . . . . ?
C24 C17 B1 C21 56.1(4) . . . . ?
C18 C17 B1 C16 60.2(4) . . . . ?
C24 C17 B1 C16 -176.4(3) . . . . ?
C18 C17 B1 N4 176.4(3) . . . . ?
C24 C17 B1 N4 -60.2(4) . . . . ?
C20 C21 B1 C17 65.4(4) . . . . ?
C22 C21 B1 C17 -58.0(4) . . . . ?
C20 C21 B1 C16 -63.8(4) . . . . ?
C22 C21 B1 C16 172.8(3) . . . . ?
C20 C21 B1 N4 179.7(3) . . . . ?
C22 C21 B1 N4 56.4(4) . . . . ?
C15 C16 B1 C17 52.7(4) . . . . ?
C15 C16 B1 C21 176.5(3) . . . . ?
C15 C16 B1 N4 -64.4(4) . . . . ?
O1 N4 B1 C17 175.9(3) . . . . ?
O1 N4 B1 C21 61.6(4) . . . . ?
O1 N4 B1 C16 -60.3(3) . . . . ?

_refine_diff_density_max         0.717
_refine_diff_density_min         -0.897
_refine_diff_density_rms         0.110


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_EN151_0m
_database_code_depnum_ccdc_archive 'CCDC 1941378'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller '
;Purdue University
United States of America
;
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C48 H76 B2 Br4 Fe2 N8, 0.409(C H2 Cl2)'
_chemical_formula_sum            'C48.41 H76.82 B2 Br4 Cl0.82 Fe2 N8'
_chemical_formula_weight         1252.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   14.0086(4)
_cell_length_b                   14.8635(4)
_cell_length_c                   15.9297(4)
_cell_angle_alpha                70.8799(10)
_cell_angle_beta                 69.8088(10)
_cell_angle_gamma                65.8643(9)
_cell_volume                     2772.76(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9946
_cell_measurement_theta_min      3.3383
_cell_measurement_theta_max      79.9029

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_F_000             1278
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    8.237
_shelx_estimated_absorpt_T_min   0.155
_shelx_estimated_absorpt_T_max   0.734
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4085
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29079
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.028
_diffrn_reflns_theta_max         80.739
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             11053
_reflns_number_gt                9165
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Apex3 v2017.3-0 (Bruker, 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev937 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
A methylene chloride molecule is partially occupied and disordered around 
an inversion center. The two C-Cl distances were restrained to a target 
value of 1.74(2) Angstrom, and Uij components of ADPs for disordered atoms 
closer to each other than 2.0 Angstrom were restrained to be similar. 
Subject to these conditions the occupancy rates refined to two times 
0.409(3). 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0547P)²+4.1772P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00098(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         11053
_refine_ls_number_parameters     614
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1272
_refine_ls_wR_factor_gt          0.1211
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.121
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.5345(16) 0.0255(14) 0.4573(10) 0.088(4) Uani 0.409(3) 1 d D U P A -1
H1A H 0.496999 0.076615 0.410593 0.106 Uiso 0.409(3) 1 calc R U P A -1
H1B H 0.612305 0.016488 0.432644 0.106 Uiso 0.409(3) 1 calc R U P A -1
Cl1 Cl 0.4897(8) 0.0755(8) 0.5539(5) 0.0478(14) Uani 0.409(3) 1 d D U P A -1
Cl2 Cl 0.5193(9) -0.0804(9) 0.4680(7) 0.079(3) Uani 0.409(3) 1 d D U P A -1
N1 N 0.3091(3) 0.2660(2) 0.1036(2) 0.0286(7) Uani 1 1 d . . . . .
H1C H 0.243521 0.271242 0.143773 0.034 Uiso 1 1 calc R U . . .
H1D H 0.322971 0.218780 0.072317 0.034 Uiso 1 1 calc R U . . .
N2 N 0.3896(2) 0.2263(2) 0.1573(2) 0.0265(6) Uani 1 1 d . . . . .
H2A H 0.354355 0.217075 0.217631 0.032 Uiso 1 1 calc R U . . .
H2B H 0.419220 0.274660 0.145800 0.032 Uiso 1 1 calc R U . . .
Fe1A Fe 0.29368(5) 0.38619(4) 0.40544(4) 0.02582(14) Uani 1 1 d . . . . .
Br1A Br 0.26287(4) 0.24664(3) 0.38895(3) 0.03521(12) Uani 1 1 d . . . . .
Br2A Br 0.47249(3) 0.37853(4) 0.38214(4) 0.04248(14) Uani 1 1 d . . . . .
N1A N 0.1865(2) 0.4326(2) 0.5278(2) 0.0248(6) Uani 1 1 d . . . . .
N2A N 0.1873(2) 0.5253(2) 0.3554(2) 0.0235(6) Uani 1 1 d . . . . .
N3A N 0.1755(2) 0.5873(2) 0.27315(19) 0.0240(6) Uani 1 1 d . . . . .
B1A B 0.2975(4) 0.3777(3) 0.0275(3) 0.0295(9) Uani 1 1 d . . . . .
C2A C 0.1940(3) 0.3823(3) 0.6138(3) 0.0305(8) Uani 1 1 d . . . . .
C1A C 0.2829(4) 0.2819(3) 0.6244(3) 0.0429(10) Uani 1 1 d . . . . .
H1AA H 0.270983 0.234897 0.601102 0.064 Uiso 1 1 calc R U . . .
H1AB H 0.283031 0.254534 0.689317 0.064 Uiso 1 1 calc R U . . .
H1AC H 0.352483 0.290842 0.589628 0.064 Uiso 1 1 calc R U . . .
C3A C 0.1226(3) 0.4229(3) 0.6878(3) 0.0343(9) Uani 1 1 d . . . . .
H3A H 0.129179 0.386808 0.748112 0.041 Uiso 1 1 calc R U . . .
C4A C 0.0431(3) 0.5140(3) 0.6754(3) 0.0336(9) Uani 1 1 d . . . . .
H4A H -0.005161 0.541787 0.726502 0.040 Uiso 1 1 calc R U . . .
C5A C 0.0337(3) 0.5654(3) 0.5872(3) 0.0304(8) Uani 1 1 d . . . . .
H5A H -0.021760 0.628474 0.576570 0.037 Uiso 1 1 calc R U . . .
C6A C 0.1069(3) 0.5227(3) 0.5151(2) 0.0237(7) Uani 1 1 d . . . . .
C7A C 0.1082(3) 0.5720(3) 0.4189(2) 0.0233(7) Uani 1 1 d . . . . .
C8A C 0.0446(3) 0.6642(3) 0.3772(3) 0.0264(7) Uani 1 1 d . . . . .
H8A H -0.016824 0.711742 0.406858 0.032 Uiso 1 1 calc R U . . .
C9A C 0.0888(3) 0.6731(3) 0.2832(2) 0.0242(7) Uani 1 1 d . . . . .
C10A C 0.0572(3) 0.7634(3) 0.2062(3) 0.0315(8) Uani 1 1 d . . . . .
C11A C -0.0513(4) 0.8381(3) 0.2458(3) 0.0430(11) Uani 1 1 d . . . . .
H11A H -0.071031 0.898579 0.197797 0.064 Uiso 1 1 calc R U . . .
H11B H -0.045011 0.857192 0.296479 0.064 Uiso 1 1 calc R U . . .
H11C H -0.107049 0.806307 0.268205 0.064 Uiso 1 1 calc R U . . .
C12A C 0.1414(4) 0.8170(3) 0.1712(3) 0.0396(10) Uani 1 1 d . . . . .
H12A H 0.212087 0.770708 0.146556 0.059 Uiso 1 1 calc R U . . .
H12B H 0.145271 0.837953 0.221905 0.059 Uiso 1 1 calc R U . . .
H12C H 0.120460 0.876629 0.122870 0.059 Uiso 1 1 calc R U . . .
C13A C 0.0453(4) 0.7351(4) 0.1271(3) 0.0439(11) Uani 1 1 d . . . . .
H13A H 0.017115 0.796681 0.083071 0.066 Uiso 1 1 calc R U . . .
H13B H -0.004815 0.696810 0.151066 0.066 Uiso 1 1 calc R U . . .
H13C H 0.115812 0.693626 0.096478 0.066 Uiso 1 1 calc R U . . .
C14A C 0.2549(3) 0.5536(3) 0.1916(2) 0.0288(8) Uani 1 1 d . . . . .
H14A H 0.327140 0.521007 0.204620 0.035 Uiso 1 1 calc R U . . .
H14B H 0.257115 0.613426 0.140739 0.035 Uiso 1 1 calc R U . . .
C15A C 0.2313(3) 0.4801(3) 0.1609(2) 0.0280(8) Uani 1 1 d . . . . .
H15A H 0.158286 0.511371 0.149348 0.034 Uiso 1 1 calc R U . . .
H15B H 0.232424 0.418580 0.210168 0.034 Uiso 1 1 calc R U . . .
C16A C 0.3147(3) 0.4511(3) 0.0734(3) 0.0295(8) Uani 1 1 d . . . . .
H16A H 0.386511 0.417770 0.087235 0.035 Uiso 1 1 calc R U . . .
H16B H 0.316508 0.514192 0.026832 0.035 Uiso 1 1 calc R U . . .
C17A C 0.1777(4) 0.4128(3) 0.0114(3) 0.0375(10) Uani 1 1 d . . . . .
H17A H 0.123814 0.420857 0.071326 0.045 Uiso 1 1 calc R U . . .
C18A C 0.1578(4) 0.5172(4) -0.0554(3) 0.0512(12) Uani 1 1 d . . . . .
H18A H 0.087207 0.537878 -0.069278 0.061 Uiso 1 1 calc R U . . .
H18B H 0.153518 0.567196 -0.024511 0.061 Uiso 1 1 calc R U . . .
C19A C 0.2453(5) 0.5203(4) -0.1465(3) 0.0632(16) Uani 1 1 d . . . . .
H19A H 0.230429 0.492945 -0.187730 0.076 Uiso 1 1 calc R U . . .
H19B H 0.238784 0.591784 -0.175770 0.076 Uiso 1 1 calc R U . . .
C20A C 0.3616(5) 0.4622(4) -0.1386(3) 0.0534(13) Uani 1 1 d . . . . .
H20A H 0.386509 0.505317 -0.121051 0.064 Uiso 1 1 calc R U . . .
H20B H 0.407103 0.450754 -0.199914 0.064 Uiso 1 1 calc R U . . .
C21A C 0.3811(4) 0.3591(3) -0.0697(3) 0.0381(10) Uani 1 1 d . . . . .
H21A H 0.456156 0.335011 -0.062156 0.046 Uiso 1 1 calc R U . . .
C22A C 0.3685(4) 0.2784(4) -0.1023(3) 0.0462(11) Uani 1 1 d . . . . .
H22A H 0.416777 0.273674 -0.164146 0.055 Uiso 1 1 calc R U . . .
H22B H 0.392737 0.212081 -0.060584 0.055 Uiso 1 1 calc R U . . .
C23A C 0.2543(5) 0.2987(4) -0.1059(4) 0.0587(14) Uani 1 1 d . . . . .
H23A H 0.250407 0.236166 -0.112058 0.070 Uiso 1 1 calc R U . . .
H23B H 0.239396 0.351082 -0.161626 0.070 Uiso 1 1 calc R U . . .
C24A C 0.1656(4) 0.3333(4) -0.0227(4) 0.0489(12) Uani 1 1 d . . . . .
H24A H 0.164371 0.273423 0.028249 0.059 Uiso 1 1 calc R U . . .
H24B H 0.095073 0.361418 -0.038606 0.059 Uiso 1 1 calc R U . . .
Fe1B Fe 0.04836(5) 0.10728(4) 0.24258(4) 0.02625(15) Uani 1 1 d . . . . .
Br1B Br 0.07705(4) 0.24493(3) 0.26521(3) 0.03745(12) Uani 1 1 d . . . . .
Br2B Br 0.03139(5) 0.10721(4) 0.10106(3) 0.04937(15) Uani 1 1 d . . . . .
N1B N -0.0741(2) 0.0698(2) 0.3558(2) 0.0256(6) Uani 1 1 d . . . . .
N2B N 0.1335(2) -0.0301(2) 0.3141(2) 0.0251(6) Uani 1 1 d . . . . .
N3B N 0.2363(2) -0.0961(2) 0.3030(2) 0.0249(6) Uani 1 1 d . . . . .
B1B B 0.4912(3) 0.1178(3) 0.1407(3) 0.0265(8) Uani 1 1 d . . . . .
C1B C -0.2117(3) 0.2243(3) 0.3032(3) 0.0387(10) Uani 1 1 d . . . . .
H1BA H -0.189763 0.212658 0.241159 0.058 Uiso 1 1 calc R U . . .
H1BB H -0.176058 0.267984 0.305046 0.058 Uiso 1 1 calc R U . . .
H1BC H -0.290149 0.256963 0.320230 0.058 Uiso 1 1 calc R U . . .
C2B C -0.1800(3) 0.1253(3) 0.3693(3) 0.0312(8) Uani 1 1 d . . . . .
C3B C -0.2549(3) 0.0918(3) 0.4428(3) 0.0383(10) Uani 1 1 d . . . . .
H3B H -0.329306 0.131067 0.451690 0.046 Uiso 1 1 calc R U . . .
C4B C -0.2212(3) 0.0013(3) 0.5032(3) 0.0376(9) Uani 1 1 d . . . . .
H4B H -0.272291 -0.021851 0.553862 0.045 Uiso 1 1 calc R U . . .
C5B C -0.1124(3) -0.0556(3) 0.4895(3) 0.0342(9) Uani 1 1 d . . . . .
H5B H -0.087425 -0.117860 0.530480 0.041 Uiso 1 1 calc R U . . .
C6B C -0.0413(3) -0.0191(3) 0.4146(2) 0.0260(7) Uani 1 1 d . . . . .
C7B C 0.0748(3) -0.0741(3) 0.3905(2) 0.0237(7) Uani 1 1 d . . . . .
C8B C 0.1400(3) -0.1674(3) 0.4285(3) 0.0281(8) Uani 1 1 d . . . . .
H8B H 0.118518 -0.213207 0.482674 0.034 Uiso 1 1 calc R U . . .
C9B C 0.2432(3) -0.1804(3) 0.3711(3) 0.0288(8) Uani 1 1 d . . . . .
C10B C 0.3431(3) -0.2744(3) 0.3765(3) 0.0343(9) Uani 1 1 d . . . . .
C11B C 0.3197(4) -0.3473(3) 0.4688(3) 0.0447(11) Uani 1 1 d . . . . .
H11D H 0.260732 -0.368568 0.472088 0.067 Uiso 1 1 calc R U . . .
H11E H 0.299040 -0.313081 0.518789 0.067 Uiso 1 1 calc R U . . .
H11F H 0.384569 -0.406598 0.474552 0.067 Uiso 1 1 calc R U . . .
C12B C 0.3656(4) -0.3266(3) 0.2994(3) 0.0420(10) Uani 1 1 d . . . . .
H12D H 0.384058 -0.282370 0.239896 0.063 Uiso 1 1 calc R U . . .
H12E H 0.301172 -0.340513 0.303930 0.063 Uiso 1 1 calc R U . . .
H12F H 0.425916 -0.390259 0.305385 0.063 Uiso 1 1 calc R U . . .
C13B C 0.4426(3) -0.2511(3) 0.3705(3) 0.0377(9) Uani 1 1 d . . . . .
H13D H 0.503721 -0.314171 0.376176 0.057 Uiso 1 1 calc R U . . .
H13E H 0.427133 -0.218238 0.420216 0.057 Uiso 1 1 calc R U . . .
H13F H 0.460650 -0.206090 0.311383 0.057 Uiso 1 1 calc R U . . .
C14B C 0.3159(3) -0.0666(3) 0.2215(3) 0.0275(8) Uani 1 1 d . . . . .
H14C H 0.282975 -0.036951 0.168485 0.033 Uiso 1 1 calc R U . . .
H14D H 0.377880 -0.127949 0.208544 0.033 Uiso 1 1 calc R U . . .
C15B C 0.3575(3) 0.0089(3) 0.2303(3) 0.0285(8) Uani 1 1 d . . . . .
H15C H 0.394283 -0.021553 0.281062 0.034 Uiso 1 1 calc R U . . .
H15D H 0.295892 0.069576 0.245474 0.034 Uiso 1 1 calc R U . . .
C16B C 0.4364(3) 0.0399(3) 0.1415(2) 0.0275(8) Uani 1 1 d . . . . .
H16C H 0.397744 0.070714 0.091987 0.033 Uiso 1 1 calc R U . . .
H16D H 0.495116 -0.022271 0.125876 0.033 Uiso 1 1 calc R U . . .
C17B C 0.5479(3) 0.0854(3) 0.2247(3) 0.0313(8) Uani 1 1 d . . . . .
H17B H 0.494055 0.072059 0.283592 0.038 Uiso 1 1 calc R U . . .
C18B C 0.6425(3) -0.0141(3) 0.2145(3) 0.0370(9) Uani 1 1 d . . . . .
H18C H 0.680741 -0.032808 0.262880 0.044 Uiso 1 1 calc R U . . .
H18D H 0.612811 -0.068077 0.225142 0.044 Uiso 1 1 calc R U . . .
C19B C 0.7249(3) -0.0106(3) 0.1208(3) 0.0408(10) Uani 1 1 d . . . . .
H19C H 0.772804 0.024008 0.119494 0.049 Uiso 1 1 calc R U . . .
H19D H 0.770238 -0.080680 0.114867 0.049 Uiso 1 1 calc R U . . .
C20B C 0.6759(3) 0.0426(3) 0.0384(3) 0.0345(9) Uani 1 1 d . . . . .
H20C H 0.650818 -0.004322 0.026470 0.041 Uiso 1 1 calc R U . . .
H20D H 0.733217 0.057310 -0.015803 0.041 Uiso 1 1 calc R U . . .
C21B C 0.5802(3) 0.1425(3) 0.0483(3) 0.0317(8) Uani 1 1 d . . . . .
H21B H 0.547649 0.165422 -0.005106 0.038 Uiso 1 1 calc R U . . .
C22B C 0.6162(3) 0.2272(3) 0.0501(3) 0.0377(9) Uani 1 1 d . . . . .
H22C H 0.676358 0.233889 -0.004301 0.045 Uiso 1 1 calc R U . . .
H22D H 0.555450 0.291634 0.044358 0.045 Uiso 1 1 calc R U . . .
C23B C 0.6527(4) 0.2121(4) 0.1358(4) 0.0454(11) Uani 1 1 d . . . . .
H23C H 0.651959 0.277867 0.138818 0.055 Uiso 1 1 calc R U . . .
H23D H 0.728101 0.165465 0.129077 0.055 Uiso 1 1 calc R U . . .
C24B C 0.5833(4) 0.1700(3) 0.2268(3) 0.0369(9) Uani 1 1 d . . . . .
H24C H 0.517834 0.226337 0.245739 0.044 Uiso 1 1 calc R U . . .
H24D H 0.624472 0.143744 0.274258 0.044 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 Cl2 1.621(14) . ?
C1 Cl1 1.735(13) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
N1 N2 1.464(4) . ?
N1 B1A 1.688(5) . ?
N1 H1C 0.9100 . ?
N1 H1D 0.9100 . ?
N2 B1B 1.685(5) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
Fe1A N2A 2.086(3) . ?
Fe1A N1A 2.131(3) . ?
Fe1A Br2A 2.3618(7) . ?
Fe1A Br1A 2.3927(7) . ?
N1A C2A 1.346(5) . ?
N1A C6A 1.355(5) . ?
N2A C7A 1.337(4) . ?
N2A N3A 1.352(4) . ?
N3A C9A 1.363(5) . ?
N3A C14A 1.467(4) . ?
B1A C21A 1.615(6) . ?
B1A C16A 1.625(6) . ?
B1A C17A 1.627(6) . ?
C2A C3A 1.383(6) . ?
C2A C1A 1.506(6) . ?
C1A H1AA 0.9800 . ?
C1A H1AB 0.9800 . ?
C1A H1AC 0.9800 . ?
C3A C4A 1.362(6) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.385(5) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.381(5) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.463(5) . ?
C7A C8A 1.389(5) . ?
C8A C9A 1.393(5) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.521(5) . ?
C10A C13A 1.532(6) . ?
C10A C11A 1.535(6) . ?
C10A C12A 1.536(6) . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
C14A C15A 1.516(5) . ?
C14A H14A 0.9900 . ?
C14A H14B 0.9900 . ?
C15A C16A 1.534(5) . ?
C15A H15A 0.9900 . ?
C15A H15B 0.9900 . ?
C16A H16A 0.9900 . ?
C16A H16B 0.9900 . ?
C17A C24A 1.539(6) . ?
C17A C18A 1.545(6) . ?
C17A H17A 1.0000 . ?
C18A C19A 1.544(8) . ?
C18A H18A 0.9900 . ?
C18A H18B 0.9900 . ?
C19A C20A 1.528(8) . ?
C19A H19A 0.9900 . ?
C19A H19B 0.9900 . ?
C20A C21A 1.546(6) . ?
C20A H20A 0.9900 . ?
C20A H20B 0.9900 . ?
C21A C22A 1.544(6) . ?
C21A H21A 1.0000 . ?
C22A C23A 1.521(8) . ?
C22A H22A 0.9900 . ?
C22A H22B 0.9900 . ?
C23A C24A 1.534(7) . ?
C23A H23A 0.9900 . ?
C23A H23B 0.9900 . ?
C24A H24A 0.9900 . ?
C24A H24B 0.9900 . ?
Fe1B N2B 2.077(3) . ?
Fe1B N1B 2.120(3) . ?
Fe1B Br2B 2.3475(7) . ?
Fe1B Br1B 2.3944(7) . ?
N1B C2B 1.350(5) . ?
N1B C6B 1.351(5) . ?
N2B C7B 1.346(4) . ?
N2B N3B 1.360(4) . ?
N3B C9B 1.356(5) . ?
N3B C14B 1.467(5) . ?
B1B C21B 1.615(6) . ?
B1B C16B 1.625(6) . ?
B1B C17B 1.629(6) . ?
C1B C2B 1.498(6) . ?
C1B H1BA 0.9800 . ?
C1B H1BB 0.9800 . ?
C1B H1BC 0.9800 . ?
C2B C3B 1.385(6) . ?
C3B C4B 1.379(6) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.388(6) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.381(5) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.465(5) . ?
C7B C8B 1.386(5) . ?
C8B C9B 1.393(5) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.524(5) . ?
C10B C11B 1.535(6) . ?
C10B C13B 1.535(6) . ?
C10B C12B 1.538(6) . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 0.9800 . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?
C14B C15B 1.520(5) . ?
C14B H14C 0.9900 . ?
C14B H14D 0.9900 . ?
C15B C16B 1.531(5) . ?
C15B H15C 0.9900 . ?
C15B H15D 0.9900 . ?
C16B H16C 0.9900 . ?
C16B H16D 0.9900 . ?
C17B C18B 1.541(6) . ?
C17B C24B 1.542(6) . ?
C17B H17B 1.0000 . ?
C18B C19B 1.540(6) . ?
C18B H18C 0.9900 . ?
C18B H18D 0.9900 . ?
C19B C20B 1.522(6) . ?
C19B H19C 0.9900 . ?
C19B H19D 0.9900 . ?
C20B C21B 1.551(5) . ?
C20B H20C 0.9900 . ?
C20B H20D 0.9900 . ?
C21B C22B 1.546(6) . ?
C21B H21B 1.0000 . ?
C22B C23B 1.537(7) . ?
C22B H22C 0.9900 . ?
C22B H22D 0.9900 . ?
C23B C24B 1.539(6) . ?
C23B H23C 0.9900 . ?
C23B H23D 0.9900 . ?
C24B H24C 0.9900 . ?
C24B H24D 0.9900 . ?

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
Cl2 C1 Cl1 118.4(10) . . ?
Cl2 C1 H1A 107.7 . . ?
Cl1 C1 H1A 107.7 . . ?
Cl2 C1 H1B 107.7 . . ?
Cl1 C1 H1B 107.7 . . ?
H1A C1 H1B 107.1 . . ?
N2 N1 B1A 119.4(3) . . ?
N2 N1 H1C 107.5 . . ?
B1A N1 H1C 107.5 . . ?
N2 N1 H1D 107.5 . . ?
B1A N1 H1D 107.5 . . ?
H1C N1 H1D 107.0 . . ?
N1 N2 B1B 118.1(3) . . ?
N1 N2 H2A 107.8 . . ?
B1B N2 H2A 107.8 . . ?
N1 N2 H2B 107.8 . . ?
B1B N2 H2B 107.8 . . ?
H2A N2 H2B 107.1 . . ?
N2A Fe1A N1A 77.39(12) . . ?
N2A Fe1A Br2A 116.59(9) . . ?
N1A Fe1A Br2A 114.21(9) . . ?
N2A Fe1A Br1A 112.61(9) . . ?
N1A Fe1A Br1A 109.27(9) . . ?
Br2A Fe1A Br1A 119.25(3) . . ?
C2A N1A C6A 118.9(3) . . ?
C2A N1A Fe1A 125.8(3) . . ?
C6A N1A Fe1A 115.2(2) . . ?
C7A N2A N3A 106.5(3) . . ?
C7A N2A Fe1A 115.7(2) . . ?
N3A N2A Fe1A 137.8(2) . . ?
N2A N3A C9A 111.1(3) . . ?
N2A N3A C14A 117.1(3) . . ?
C9A N3A C14A 131.8(3) . . ?
C21A B1A C16A 115.0(4) . . ?
C21A B1A C17A 105.9(3) . . ?
C16A B1A C17A 115.3(3) . . ?
C21A B1A N1 109.4(3) . . ?
C16A B1A N1 107.0(3) . . ?
C17A B1A N1 103.6(3) . . ?
N1A C2A C3A 120.4(4) . . ?
N1A C2A C1A 116.9(4) . . ?
C3A C2A C1A 122.7(4) . . ?
C2A C1A H1AA 109.5 . . ?
C2A C1A H1AB 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
C2A C1A H1AC 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
C4A C3A C2A 120.9(4) . . ?
C4A C3A H3A 119.5 . . ?
C2A C3A H3A 119.5 . . ?
C3A C4A C5A 119.0(4) . . ?
C3A C4A H4A 120.5 . . ?
C5A C4A H4A 120.5 . . ?
C6A C5A C4A 118.4(4) . . ?
C6A C5A H5A 120.8 . . ?
C4A C5A H5A 120.8 . . ?
N1A C6A C5A 122.4(3) . . ?
N1A C6A C7A 114.3(3) . . ?
C5A C6A C7A 123.3(3) . . ?
N2A C7A C8A 110.2(3) . . ?
N2A C7A C6A 117.4(3) . . ?
C8A C7A C6A 132.3(3) . . ?
C7A C8A C9A 106.1(3) . . ?
C7A C8A H8A 126.9 . . ?
C9A C8A H8A 126.9 . . ?
N3A C9A C8A 106.0(3) . . ?
N3A C9A C10A 125.5(3) . . ?
C8A C9A C10A 128.2(3) . . ?
C9A C10A C13A 113.2(3) . . ?
C9A C10A C11A 108.3(3) . . ?
C13A C10A C11A 108.4(4) . . ?
C9A C10A C12A 108.9(3) . . ?
C13A C10A C12A 110.4(4) . . ?
C11A C10A C12A 107.5(4) . . ?
C10A C11A H11A 109.5 . . ?
C10A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C10A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C10A C12A H12A 109.5 . . ?
C10A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C10A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C10A C13A H13A 109.5 . . ?
C10A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
C10A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
N3A C14A C15A 113.6(3) . . ?
N3A C14A H14A 108.8 . . ?
C15A C14A H14A 108.8 . . ?
N3A C14A H14B 108.8 . . ?
C15A C14A H14B 108.8 . . ?
H14A C14A H14B 107.7 . . ?
C14A C15A C16A 111.0(3) . . ?
C14A C15A H15A 109.4 . . ?
C16A C15A H15A 109.4 . . ?
C14A C15A H15B 109.4 . . ?
C16A C15A H15B 109.4 . . ?
H15A C15A H15B 108.0 . . ?
C15A C16A B1A 117.5(3) . . ?
C15A C16A H16A 107.9 . . ?
B1A C16A H16A 107.9 . . ?
C15A C16A H16B 107.9 . . ?
B1A C16A H16B 107.9 . . ?
H16A C16A H16B 107.2 . . ?
C24A C17A C18A 113.1(4) . . ?
C24A C17A B1A 111.6(3) . . ?
C18A C17A B1A 107.4(4) . . ?
C24A C17A H17A 108.2 . . ?
C18A C17A H17A 108.2 . . ?
B1A C17A H17A 108.2 . . ?
C19A C18A C17A 114.3(4) . . ?
C19A C18A H18A 108.7 . . ?
C17A C18A H18A 108.7 . . ?
C19A C18A H18B 108.7 . . ?
C17A C18A H18B 108.7 . . ?
H18A C18A H18B 107.6 . . ?
C20A C19A C18A 115.7(4) . . ?
C20A C19A H19A 108.4 . . ?
C18A C19A H19A 108.4 . . ?
C20A C19A H19B 108.4 . . ?
C18A C19A H19B 108.4 . . ?
H19A C19A H19B 107.4 . . ?
C19A C20A C21A 116.3(4) . . ?
C19A C20A H20A 108.2 . . ?
C21A C20A H20A 108.2 . . ?
C19A C20A H20B 108.2 . . ?
C21A C20A H20B 108.2 . . ?
H20A C20A H20B 107.4 . . ?
C22A C21A C20A 112.4(4) . . ?
C22A C21A B1A 111.5(4) . . ?
C20A C21A B1A 107.4(3) . . ?
C22A C21A H21A 108.5 . . ?
C20A C21A H21A 108.5 . . ?
B1A C21A H21A 108.5 . . ?
C23A C22A C21A 114.5(4) . . ?
C23A C22A H22A 108.6 . . ?
C21A C22A H22A 108.6 . . ?
C23A C22A H22B 108.6 . . ?
C21A C22A H22B 108.6 . . ?
H22A C22A H22B 107.6 . . ?
C22A C23A C24A 115.1(4) . . ?
C22A C23A H23A 108.5 . . ?
C24A C23A H23A 108.5 . . ?
C22A C23A H23B 108.5 . . ?
C24A C23A H23B 108.5 . . ?
H23A C23A H23B 107.5 . . ?
C23A C24A C17A 115.1(4) . . ?
C23A C24A H24A 108.5 . . ?
C17A C24A H24A 108.5 . . ?
C23A C24A H24B 108.5 . . ?
C17A C24A H24B 108.5 . . ?
H24A C24A H24B 107.5 . . ?
N2B Fe1B N1B 77.39(12) . . ?
N2B Fe1B Br2B 116.37(9) . . ?
N1B Fe1B Br2B 113.76(9) . . ?
N2B Fe1B Br1B 111.20(9) . . ?
N1B Fe1B Br1B 107.49(9) . . ?
Br2B Fe1B Br1B 121.81(3) . . ?
C2B N1B C6B 119.6(3) . . ?
C2B N1B Fe1B 124.7(3) . . ?
C6B N1B Fe1B 115.6(2) . . ?
C7B N2B N3B 106.2(3) . . ?
C7B N2B Fe1B 116.1(2) . . ?
N3B N2B Fe1B 137.5(2) . . ?
C9B N3B N2B 110.9(3) . . ?
C9B N3B C14B 132.4(3) . . ?
N2B N3B C14B 116.7(3) . . ?
C21B B1B C16B 116.1(3) . . ?
C21B B1B C17B 105.8(3) . . ?
C16B B1B C17B 115.0(3) . . ?
C21B B1B N2 108.7(3) . . ?
C16B B1B N2 106.4(3) . . ?
C17B B1B N2 104.1(3) . . ?
C2B C1B H1BA 109.5 . . ?
C2B C1B H1BB 109.5 . . ?
H1BA C1B H1BB 109.5 . . ?
C2B C1B H1BC 109.5 . . ?
H1BA C1B H1BC 109.5 . . ?
H1BB C1B H1BC 109.5 . . ?
N1B C2B C3B 120.5(4) . . ?
N1B C2B C1B 117.4(3) . . ?
C3B C2B C1B 122.1(4) . . ?
C4B C3B C2B 119.9(4) . . ?
C4B C3B H3B 120.0 . . ?
C2B C3B H3B 120.0 . . ?
C3B C4B C5B 119.6(4) . . ?
C3B C4B H4B 120.2 . . ?
C5B C4B H4B 120.2 . . ?
C6B C5B C4B 118.1(4) . . ?
C6B C5B H5B 120.9 . . ?
C4B C5B H5B 120.9 . . ?
N1B C6B C5B 122.3(4) . . ?
N1B C6B C7B 114.3(3) . . ?
C5B C6B C7B 123.3(3) . . ?
N2B C7B C8B 110.2(3) . . ?
N2B C7B C6B 116.6(3) . . ?
C8B C7B C6B 133.2(3) . . ?
C7B C8B C9B 106.1(3) . . ?
C7B C8B H8B 127.0 . . ?
C9B C8B H8B 127.0 . . ?
N3B C9B C8B 106.6(3) . . ?
N3B C9B C10B 125.6(4) . . ?
C8B C9B C10B 127.5(4) . . ?
C9B C10B C11B 108.6(4) . . ?
C9B C10B C13B 112.8(3) . . ?
C11B C10B C13B 107.7(4) . . ?
C9B C10B C12B 108.7(3) . . ?
C11B C10B C12B 108.4(4) . . ?
C13B C10B C12B 110.5(4) . . ?
C10B C11B H11D 109.5 . . ?
C10B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C10B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C10B C12B H12D 109.5 . . ?
C10B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C10B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C10B C13B H13D 109.5 . . ?
C10B C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
C10B C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
N3B C14B C15B 114.2(3) . . ?
N3B C14B H14C 108.7 . . ?
C15B C14B H14C 108.7 . . ?
N3B C14B H14D 108.7 . . ?
C15B C14B H14D 108.7 . . ?
H14C C14B H14D 107.6 . . ?
C14B C15B C16B 111.4(3) . . ?
C14B C15B H15C 109.3 . . ?
C16B C15B H15C 109.3 . . ?
C14B C15B H15D 109.3 . . ?
C16B C15B H15D 109.3 . . ?
H15C C15B H15D 108.0 . . ?
C15B C16B B1B 117.5(3) . . ?
C15B C16B H16C 107.9 . . ?
B1B C16B H16C 107.9 . . ?
C15B C16B H16D 107.9 . . ?
B1B C16B H16D 107.9 . . ?
H16C C16B H16D 107.2 . . ?
C18B C17B C24B 112.8(3) . . ?
C18B C17B B1B 107.4(3) . . ?
C24B C17B B1B 111.7(3) . . ?
C18B C17B H17B 108.3 . . ?
C24B C17B H17B 108.3 . . ?
B1B C17B H17B 108.3 . . ?
C19B C18B C17B 114.8(4) . . ?
C19B C18B H18C 108.6 . . ?
C17B C18B H18C 108.6 . . ?
C19B C18B H18D 108.6 . . ?
C17B C18B H18D 108.6 . . ?
H18C C18B H18D 107.5 . . ?
C20B C19B C18B 114.9(3) . . ?
C20B C19B H19C 108.5 . . ?
C18B C19B H19C 108.5 . . ?
C20B C19B H19D 108.5 . . ?
C18B C19B H19D 108.5 . . ?
H19C C19B H19D 107.5 . . ?
C19B C20B C21B 115.3(3) . . ?
C19B C20B H20C 108.4 . . ?
C21B C20B H20C 108.4 . . ?
C19B C20B H20D 108.4 . . ?
C21B C20B H20D 108.4 . . ?
H20C C20B H20D 107.5 . . ?
C22B C21B C20B 112.2(3) . . ?
C22B C21B B1B 111.6(3) . . ?
C20B C21B B1B 107.4(3) . . ?
C22B C21B H21B 108.5 . . ?
C20B C21B H21B 108.5 . . ?
B1B C21B H21B 108.5 . . ?
C23B C22B C21B 115.8(4) . . ?
C23B C22B H22C 108.3 . . ?
C21B C22B H22C 108.3 . . ?
C23B C22B H22D 108.3 . . ?
C21B C22B H22D 108.3 . . ?
H22C C22B H22D 107.4 . . ?
C22B C23B C24B 114.8(4) . . ?
C22B C23B H23C 108.6 . . ?
C24B C23B H23C 108.6 . . ?
C22B C23B H23D 108.6 . . ?
C24B C23B H23D 108.6 . . ?
H23C C23B H23D 107.5 . . ?
C23B C24B C17B 115.5(4) . . ?
C23B C24B H24C 108.4 . . ?
C17B C24B H24C 108.4 . . ?
C23B C24B H24D 108.4 . . ?
C17B C24B H24D 108.4 . . ?
H24C C24B H24D 107.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
B1A N1 N2 B1B -115.5(3) . . . . ?
C7A N2A N3A C9A -0.5(4) . . . . ?
Fe1A N2A N3A C9A -178.2(3) . . . . ?
C7A N2A N3A C14A 178.7(3) . . . . ?
Fe1A N2A N3A C14A 1.1(5) . . . . ?
N2 N1 B1A C21A 87.1(4) . . . . ?
N2 N1 B1A C16A -38.1(4) . . . . ?
N2 N1 B1A C17A -160.4(3) . . . . ?
C6A N1A C2A C3A -1.3(6) . . . . ?
Fe1A N1A C2A C3A 176.5(3) . . . . ?
C6A N1A C2A C1A 179.1(4) . . . . ?
Fe1A N1A C2A C1A -3.1(5) . . . . ?
N1A C2A C3A C4A 0.5(6) . . . . ?
C1A C2A C3A C4A -179.9(4) . . . . ?
C2A C3A C4A C5A 0.7(6) . . . . ?
C3A C4A C5A C6A -1.1(6) . . . . ?
C2A N1A C6A C5A 0.8(5) . . . . ?
Fe1A N1A C6A C5A -177.2(3) . . . . ?
C2A N1A C6A C7A 178.4(3) . . . . ?
Fe1A N1A C6A C7A 0.4(4) . . . . ?
C4A C5A C6A N1A 0.3(6) . . . . ?
C4A C5A C6A C7A -177.0(4) . . . . ?
N3A N2A C7A C8A 0.5(4) . . . . ?
Fe1A N2A C7A C8A 178.7(2) . . . . ?
N3A N2A C7A C6A -176.4(3) . . . . ?
Fe1A N2A C7A C6A 1.8(4) . . . . ?
N1A C6A C7A N2A -1.5(5) . . . . ?
C5A C6A C7A N2A 176.1(3) . . . . ?
N1A C6A C7A C8A -177.5(4) . . . . ?
C5A C6A C7A C8A 0.0(6) . . . . ?
N2A C7A C8A C9A -0.3(4) . . . . ?
C6A C7A C8A C9A 176.0(4) . . . . ?
N2A N3A C9A C8A 0.4(4) . . . . ?
C14A N3A C9A C8A -178.7(4) . . . . ?
N2A N3A C9A C10A 174.3(3) . . . . ?
C14A N3A C9A C10A -4.8(6) . . . . ?
C7A C8A C9A N3A -0.1(4) . . . . ?
C7A C8A C9A C10A -173.8(4) . . . . ?
N3A C9A C10A C13A 53.9(5) . . . . ?
C8A C9A C10A C13A -133.5(4) . . . . ?
N3A C9A C10A C11A 174.1(4) . . . . ?
C8A C9A C10A C11A -13.3(6) . . . . ?
N3A C9A C10A C12A -69.3(5) . . . . ?
C8A C9A C10A C12A 103.3(4) . . . . ?
N2A N3A C14A C15A 81.8(4) . . . . ?
C9A N3A C14A C15A -99.1(5) . . . . ?
N3A C14A C15A C16A 177.8(3) . . . . ?
C14A C15A C16A B1A -176.5(3) . . . . ?
C21A B1A C16A C15A 174.1(3) . . . . ?
C17A B1A C16A C15A 50.4(5) . . . . ?
N1 B1A C16A C15A -64.2(4) . . . . ?
C21A B1A C17A C24A 57.6(5) . . . . ?
C16A B1A C17A C24A -174.0(4) . . . . ?
N1 B1A C17A C24A -57.5(4) . . . . ?
C21A B1A C17A C18A -66.9(4) . . . . ?
C16A B1A C17A C18A 61.5(5) . . . . ?
N1 B1A C17A C18A 178.0(3) . . . . ?
C24A C17A C18A C19A -68.8(6) . . . . ?
B1A C17A C18A C19A 54.8(5) . . . . ?
C17A C18A C19A C20A -41.0(7) . . . . ?
C18A C19A C20A C21A 40.0(7) . . . . ?
C19A C20A C21A C22A 70.6(5) . . . . ?
C19A C20A C21A B1A -52.4(6) . . . . ?
C16A B1A C21A C22A 172.8(4) . . . . ?
C17A B1A C21A C22A -58.7(4) . . . . ?
N1 B1A C21A C22A 52.4(5) . . . . ?
C16A B1A C21A C20A -63.7(5) . . . . ?
C17A B1A C21A C20A 64.9(5) . . . . ?
N1 B1A C21A C20A 175.9(4) . . . . ?
C20A C21A C22A C23A -67.0(5) . . . . ?
B1A C21A C22A C23A 53.7(5) . . . . ?
C21A C22A C23A C24A -44.2(6) . . . . ?
C22A C23A C24A C17A 43.4(6) . . . . ?
C18A C17A C24A C23A 69.8(5) . . . . ?
B1A C17A C24A C23A -51.5(5) . . . . ?
C7B N2B N3B C9B -0.2(4) . . . . ?
Fe1B N2B N3B C9B -175.0(3) . . . . ?
C7B N2B N3B C14B 177.9(3) . . . . ?
Fe1B N2B N3B C14B 3.0(5) . . . . ?
N1 N2 B1B C21B 79.1(4) . . . . ?
N1 N2 B1B C16B -46.6(4) . . . . ?
N1 N2 B1B C17B -168.5(3) . . . . ?
C6B N1B C2B C3B 0.0(6) . . . . ?
Fe1B N1B C2B C3B 176.4(3) . . . . ?
C6B N1B C2B C1B 178.7(4) . . . . ?
Fe1B N1B C2B C1B -4.9(5) . . . . ?
N1B C2B C3B C4B 0.4(7) . . . . ?
C1B C2B C3B C4B -178.2(4) . . . . ?
C2B C3B C4B C5B -0.2(7) . . . . ?
C3B C4B C5B C6B -0.4(6) . . . . ?
C2B N1B C6B C5B -0.7(6) . . . . ?
Fe1B N1B C6B C5B -177.4(3) . . . . ?
C2B N1B C6B C7B 177.6(3) . . . . ?
Fe1B N1B C6B C7B 0.9(4) . . . . ?
C4B C5B C6B N1B 0.9(6) . . . . ?
C4B C5B C6B C7B -177.3(4) . . . . ?
N3B N2B C7B C8B 0.5(4) . . . . ?
Fe1B N2B C7B C8B 176.6(2) . . . . ?
N3B N2B C7B C6B -177.0(3) . . . . ?
Fe1B N2B C7B C6B -0.9(4) . . . . ?
N1B C6B C7B N2B 0.0(5) . . . . ?
C5B C6B C7B N2B 178.3(4) . . . . ?
N1B C6B C7B C8B -176.8(4) . . . . ?
C5B C6B C7B C8B 1.5(7) . . . . ?
N2B C7B C8B C9B -0.6(4) . . . . ?
C6B C7B C8B C9B 176.4(4) . . . . ?
N2B N3B C9B C8B -0.2(4) . . . . ?
C14B N3B C9B C8B -177.8(4) . . . . ?
N2B N3B C9B C10B 174.1(3) . . . . ?
C14B N3B C9B C10B -3.6(6) . . . . ?
C7B C8B C9B N3B 0.4(4) . . . . ?
C7B C8B C9B C10B -173.6(4) . . . . ?
N3B C9B C10B C11B 174.5(4) . . . . ?
C8B C9B C10B C11B -12.5(6) . . . . ?
N3B C9B C10B C13B 55.1(5) . . . . ?
C8B C9B C10B C13B -131.8(4) . . . . ?
N3B C9B C10B C12B -67.8(5) . . . . ?
C8B C9B C10B C12B 105.2(5) . . . . ?
C9B N3B C14B C15B -103.2(5) . . . . ?
N2B N3B C14B C15B 79.3(4) . . . . ?
N3B C14B C15B C16B -177.5(3) . . . . ?
C14B C15B C16B B1B -178.1(3) . . . . ?
C21B B1B C16B C15B 175.8(3) . . . . ?
C17B B1B C16B C15B 51.5(4) . . . . ?
N2 B1B C16B C15B -63.2(4) . . . . ?
C21B B1B C17B C18B -65.5(4) . . . . ?
C16B B1B C17B C18B 64.0(4) . . . . ?
N2 B1B C17B C18B 180.0(3) . . . . ?
C21B B1B C17B C24B 58.7(4) . . . . ?
C16B B1B C17B C24B -171.8(3) . . . . ?
N2 B1B C17B C24B -55.8(4) . . . . ?
C24B C17B C18B C19B -68.6(5) . . . . ?
B1B C17B C18B C19B 54.9(5) . . . . ?
C17B C18B C19B C20B -43.2(5) . . . . ?
C18B C19B C20B C21B 43.0(5) . . . . ?
C19B C20B C21B C22B 68.3(5) . . . . ?
C19B C20B C21B B1B -54.7(5) . . . . ?
C16B B1B C21B C22B 172.7(3) . . . . ?
C17B B1B C21B C22B -58.4(4) . . . . ?
N2 B1B C21B C22B 52.9(4) . . . . ?
C16B B1B C21B C20B -63.9(4) . . . . ?
C17B B1B C21B C20B 65.1(4) . . . . ?
N2 B1B C21B C20B 176.4(3) . . . . ?
C20B C21B C22B C23B -69.0(5) . . . . ?
B1B C21B C22B C23B 51.7(5) . . . . ?
C21B C22B C23B C24B -41.1(5) . . . . ?
C22B C23B C24B C17B 41.2(5) . . . . ?
C18B C17B C24B C23B 69.4(5) . . . . ?
B1B C17B C24B C23B -51.8(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1C Br1B 0.91 2.54 3.438(3) 167.7 . yes
N2 H2A Br1A 0.91 2.68 3.554(3) 160.8 . yes

_refine_diff_density_max         0.861
_refine_diff_density_min         -1.071
_refine_diff_density_rms         0.097


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_EN111_0m
_database_code_depnum_ccdc_archive 'CCDC 1941372'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller '
;Purdue University
United States of America
;
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C24 H36 B Cl2 Fe N3), C5 H12'
_chemical_formula_sum            'C53 H84 B2 Cl4 Fe2 N6'
_chemical_formula_weight         1080.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   15.5954(4)
_cell_length_b                   11.5756(3)
_cell_length_c                   16.2879(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.1056(12)
_cell_angle_gamma                90
_cell_volume                     2939.84(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9873
_cell_measurement_theta_min      4.6868
_cell_measurement_theta_max      80.4532

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_F_000             1148
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    5.912
_shelx_estimated_absorpt_T_min   0.343
_shelx_estimated_absorpt_T_max   0.537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3704
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24817
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.687
_diffrn_reflns_theta_max         80.712
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             6096
_reflns_number_gt                5357
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Apex3 v2017.3-0 (Bruker, 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev937 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
A pentane molecule is disordered around an inversion center. 
C-C distances were restrained to target values of 1.55(2) and 1.50(2)
Angstrom and 1.3 distances to at least 2.50(2) Angstrom. Uij components 
of ADPs for disordered atoms closer to each other than 2.0 Angstrom 
were restrained to be similar. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0432P)²+1.3084P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6096
_refine_ls_number_parameters     332
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0950
_refine_ls_wR_factor_gt          0.0920
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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 0.53692(14) 1.03864(18) 0.12601(12) 0.0309(4) Uani 1 1 d . . . . .
H1A H 0.588189 1.042283 0.092252 0.046 Uiso 1 1 calc R U . . .
H1B H 0.519927 1.117005 0.141619 0.046 Uiso 1 1 calc R U . . .
H1C H 0.490096 1.002031 0.094576 0.046 Uiso 1 1 calc R U . . .
C2 C 0.55606(11) 0.96930(16) 0.20170(11) 0.0219(4) Uani 1 1 d . . . . .
C3 C 0.54487(12) 1.01343(16) 0.28058(11) 0.0244(4) Uani 1 1 d . . . . .
H3 H 0.525429 1.090499 0.287650 0.029 Uiso 1 1 calc R U . . .
C4 C 0.56207(12) 0.94503(17) 0.34809(11) 0.0250(4) Uani 1 1 d . . . . .
H4 H 0.552345 0.973617 0.401780 0.030 Uiso 1 1 calc R U . . .
C5 C 0.59366(12) 0.83423(17) 0.33728(11) 0.0245(4) Uani 1 1 d . . . . .
H5 H 0.607059 0.786223 0.383068 0.029 Uiso 1 1 calc R U . . .
C6 C 0.60511(11) 0.79558(15) 0.25774(10) 0.0197(3) Uani 1 1 d . . . . .
C7 C 0.63842(11) 0.68097(15) 0.23876(10) 0.0198(3) Uani 1 1 d . . . . .
C8 C 0.66558(11) 0.58942(16) 0.28830(11) 0.0229(4) Uani 1 1 d . . . . .
H8 H 0.669750 0.588438 0.346565 0.027 Uiso 1 1 calc R U . . .
C9 C 0.68524(11) 0.50022(16) 0.23535(11) 0.0230(4) Uani 1 1 d . . . . .
C10 C 0.71649(12) 0.37970(17) 0.25699(12) 0.0288(4) Uani 1 1 d . . . . .
C11 C 0.80421(14) 0.3576(2) 0.21867(16) 0.0419(5) Uani 1 1 d . . . . .
H11A H 0.798118 0.358610 0.158679 0.063 Uiso 1 1 calc R U . . .
H11B H 0.825968 0.282133 0.236581 0.063 Uiso 1 1 calc R U . . .
H11C H 0.844503 0.418108 0.236308 0.063 Uiso 1 1 calc R U . . .
C12 C 0.65070(15) 0.28854(18) 0.23031(16) 0.0394(5) Uani 1 1 d . . . . .
H12A H 0.643818 0.289734 0.170380 0.059 Uiso 1 1 calc R U . . .
H12B H 0.595511 0.305447 0.255455 0.059 Uiso 1 1 calc R U . . .
H12C H 0.670593 0.212017 0.247985 0.059 Uiso 1 1 calc R U . . .
C13 C 0.72755(17) 0.3728(2) 0.35067(14) 0.0455(6) Uani 1 1 d . . . . .
H13A H 0.748986 0.296052 0.366088 0.068 Uiso 1 1 calc R U . . .
H13B H 0.672128 0.386183 0.376372 0.068 Uiso 1 1 calc R U . . .
H13C H 0.768610 0.431689 0.369389 0.068 Uiso 1 1 calc R U . . .
C14 C 0.68085(12) 0.48751(16) 0.07680(11) 0.0242(4) Uani 1 1 d . . . . .
H14A H 0.628214 0.500549 0.043126 0.029 Uiso 1 1 calc R U . . .
H14B H 0.687962 0.403102 0.083968 0.029 Uiso 1 1 calc R U . . .
C15 C 0.75748(12) 0.53484(17) 0.03125(11) 0.0258(4) Uani 1 1 d . . . . .
H15A H 0.809665 0.527576 0.066447 0.031 Uiso 1 1 calc R U . . .
H15B H 0.748276 0.617872 0.019482 0.031 Uiso 1 1 calc R U . . .
C16 C 0.77076(12) 0.46997(18) -0.04936(11) 0.0280(4) Uani 1 1 d . . . . .
H16A H 0.715802 0.471675 -0.080787 0.034 Uiso 1 1 calc R U . . .
H16B H 0.782752 0.388162 -0.035631 0.034 Uiso 1 1 calc R U . . .
C17 C 0.90700(14) 0.6133(2) -0.09066(14) 0.0383(5) Uani 1 1 d . . . . .
H17 H 0.904611 0.637274 -0.031764 0.046 Uiso 1 1 calc R U . . .
C18 C 0.99977(14) 0.5772(2) -0.11197(15) 0.0451(6) Uani 1 1 d . . . . .
H18A H 1.022203 0.631866 -0.153085 0.054 Uiso 1 1 calc R U . . .
H18B H 1.036467 0.583542 -0.061897 0.054 Uiso 1 1 calc R U . . .
C19 C 1.00645(15) 0.4563(2) -0.14527(16) 0.0475(6) Uani 1 1 d . . . . .
H19A H 0.994977 0.400766 -0.100569 0.057 Uiso 1 1 calc R U . . .
H19B H 1.065820 0.443060 -0.163568 0.057 Uiso 1 1 calc R U . . .
C20 C 0.94467(14) 0.4324(2) -0.21672(14) 0.0429(6) Uani 1 1 d . . . . .
H20A H 0.947493 0.349345 -0.230950 0.051 Uiso 1 1 calc R U . . .
H20B H 0.963097 0.477014 -0.265137 0.051 Uiso 1 1 calc R U . . .
C21 C 0.85031(13) 0.4645(2) -0.19761(12) 0.0365(5) Uani 1 1 d . . . . .
H21 H 0.812466 0.395407 -0.205262 0.044 Uiso 1 1 calc R U . . .
C22 C 0.81714(16) 0.5653(3) -0.25160(15) 0.0551(7) Uani 1 1 d . . . . .
H22A H 0.821605 0.543343 -0.310099 0.066 Uiso 1 1 calc R U . . .
H22B H 0.755769 0.578481 -0.240277 0.066 Uiso 1 1 calc R U . . .
C23 C 0.86613(19) 0.6772(3) -0.23703(18) 0.0621(8) Uani 1 1 d . . . . .
H23A H 0.837597 0.740007 -0.268461 0.074 Uiso 1 1 calc R U . . .
H23B H 0.924912 0.668509 -0.258076 0.074 Uiso 1 1 calc R U . . .
C24 C 0.87160(19) 0.7113(2) -0.14659(19) 0.0555(7) Uani 1 1 d . . . . .
H24A H 0.813719 0.733141 -0.128120 0.067 Uiso 1 1 calc R U . . .
H24B H 0.909122 0.779842 -0.140551 0.067 Uiso 1 1 calc R U . . .
C25 C 1.1382(9) 0.8624(10) -0.0434(7) 0.133(5) Uani 0.5 1 d D U P A -1
H25A H 1.122329 0.864592 -0.101907 0.199 Uiso 0.5 1 calc R U P A -1
H25B H 1.164818 0.787823 -0.030253 0.199 Uiso 0.5 1 calc R U P A -1
H25C H 1.178812 0.924777 -0.030861 0.199 Uiso 0.5 1 calc R U P A -1
C26 C 1.0555(13) 0.8784(19) 0.0092(17) 0.188(6) Uani 0.5 1 d D U P A -1
H26A H 1.012857 0.816999 -0.002720 0.225 Uiso 0.5 1 calc R U P A -1
H26B H 1.069737 0.878221 0.068733 0.225 Uiso 0.5 1 calc R U P A -1
C27 C 1.0216(13) 1.000(2) -0.020(2) 0.182(6) Uani 0.5 1 d D U P A -1
H27A H 1.062893 1.060353 -0.002163 0.218 Uiso 0.5 1 calc R U P A -1
H27B H 1.016675 1.001369 -0.080288 0.218 Uiso 0.5 1 calc R U P A -1
C28 C 0.9380(12) 1.023(2) 0.0155(19) 0.178(6) Uani 0.5 1 d D U P A -1
H28A H 0.939505 1.008479 0.075368 0.214 Uiso 0.5 1 calc R U P A -1
H28B H 0.893460 0.973765 -0.010320 0.214 Uiso 0.5 1 calc R U P A -1
C29 C 0.9178(11) 1.1569(17) -0.0024(15) 0.181(7) Uani 0.5 1 d D U P A -1
H29A H 0.943001 1.179379 -0.054671 0.272 Uiso 0.5 1 calc R U P A -1
H29B H 0.942483 1.204360 0.041954 0.272 Uiso 0.5 1 calc R U P A -1
H29C H 0.855596 1.168593 -0.005358 0.272 Uiso 0.5 1 calc R U P A -1
B1 B 0.84263(14) 0.5125(2) -0.10762(14) 0.0295(5) Uani 1 1 d . . . . .
N1 N 0.58480(9) 0.86115(13) 0.19119(9) 0.0203(3) Uani 1 1 d . . . . .
N2 N 0.64189(9) 0.65100(13) 0.15922(8) 0.0202(3) Uani 1 1 d . . . . .
N3 N 0.67023(9) 0.54118(13) 0.15771(9) 0.0215(3) Uani 1 1 d . . . . .
Cl1 Cl 0.70045(3) 0.86230(4) 0.00507(3) 0.03491(13) Uani 1 1 d . . . . .
Cl2 Cl 0.47168(3) 0.71613(4) 0.02518(3) 0.03269(12) Uani 1 1 d . . . . .
Fe1 Fe 0.59832(2) 0.77567(2) 0.07685(2) 0.02106(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.496(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 N1 1.342(2) . ?
C2 C3 1.397(2) . ?
C3 C4 1.377(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(2) . ?
C5 H5 0.9500 . ?
C6 N1 1.356(2) . ?
C6 C7 1.460(3) . ?
C7 N2 1.343(2) . ?
C7 C8 1.393(2) . ?
C8 C9 1.384(3) . ?
C8 H8 0.9500 . ?
C9 N3 1.367(2) . ?
C9 C10 1.517(3) . ?
C10 C12 1.529(3) . ?
C10 C13 1.534(3) . ?
C10 C11 1.536(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 N3 1.469(2) . ?
C14 C15 1.521(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.530(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 B1 1.562(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C24 1.549(4) . ?
C17 C18 1.552(3) . ?
C17 B1 1.561(3) . ?
C17 H17 1.0000 . ?
C18 C19 1.506(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.522(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.555(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.545(4) . ?
C21 B1 1.574(3) . ?
C21 H21 1.0000 . ?
C22 C23 1.520(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.526(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.573(17) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.570(17) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.460(14) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.602(16) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
N1 Fe1 2.1230(14) . ?
N2 N3 1.346(2) . ?
N2 Fe1 2.0759(15) . ?
Cl1 Fe1 2.2320(5) . ?
Cl2 Fe1 2.2404(5) . ?

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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 120.44(16) . . ?
N1 C2 C1 117.20(16) . . ?
C3 C2 C1 122.36(17) . . ?
C4 C3 C2 119.89(17) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 119.66(16) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 118.03(17) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
N1 C6 C5 122.32(17) . . ?
N1 C6 C7 114.71(15) . . ?
C5 C6 C7 122.97(16) . . ?
N2 C7 C8 110.17(16) . . ?
N2 C7 C6 117.39(15) . . ?
C8 C7 C6 132.38(16) . . ?
C9 C8 C7 105.98(15) . . ?
C9 C8 H8 127.0 . . ?
C7 C8 H8 127.0 . . ?
N3 C9 C8 106.37(16) . . ?
N3 C9 C10 125.63(16) . . ?
C8 C9 C10 128.00(17) . . ?
C9 C10 C12 110.97(16) . . ?
C9 C10 C13 107.96(17) . . ?
C12 C10 C13 107.98(18) . . ?
C9 C10 C11 110.07(16) . . ?
C12 C10 C11 111.58(18) . . ?
C13 C10 C11 108.15(18) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C15 112.86(15) . . ?
N3 C14 H14A 109.0 . . ?
C15 C14 H14A 109.0 . . ?
N3 C14 H14B 109.0 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 C16 111.25(15) . . ?
C14 C15 H15A 109.4 . . ?
C16 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
C16 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C15 C16 B1 118.51(17) . . ?
C15 C16 H16A 107.7 . . ?
B1 C16 H16A 107.7 . . ?
C15 C16 H16B 107.7 . . ?
B1 C16 H16B 107.7 . . ?
H16A C16 H16B 107.1 . . ?
C24 C17 C18 112.9(2) . . ?
C24 C17 B1 102.9(2) . . ?
C18 C17 B1 111.00(19) . . ?
C24 C17 H17 110.0 . . ?
C18 C17 H17 110.0 . . ?
B1 C17 H17 110.0 . . ?
C19 C18 C17 113.72(19) . . ?
C19 C18 H18A 108.8 . . ?
C17 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C17 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
C18 C19 C20 113.4(2) . . ?
C18 C19 H19A 108.9 . . ?
C20 C19 H19A 108.9 . . ?
C18 C19 H19B 108.9 . . ?
C20 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C19 C20 C21 113.03(17) . . ?
C19 C20 H20A 109.0 . . ?
C21 C20 H20A 109.0 . . ?
C19 C20 H20B 109.0 . . ?
C21 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C22 C21 C20 111.99(19) . . ?
C22 C21 B1 103.45(19) . . ?
C20 C21 B1 111.10(17) . . ?
C22 C21 H21 110.0 . . ?
C20 C21 H21 110.0 . . ?
B1 C21 H21 110.0 . . ?
C23 C22 C21 113.2(2) . . ?
C23 C22 H22A 108.9 . . ?
C21 C22 H22A 108.9 . . ?
C23 C22 H22B 108.9 . . ?
C21 C22 H22B 108.9 . . ?
H22A C22 H22B 107.8 . . ?
C22 C23 C24 112.9(2) . . ?
C22 C23 H23A 109.0 . . ?
C24 C23 H23A 109.0 . . ?
C22 C23 H23B 109.0 . . ?
C24 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C23 C24 C17 113.0(2) . . ?
C23 C24 H24A 109.0 . . ?
C17 C24 H24A 109.0 . . ?
C23 C24 H24B 109.0 . . ?
C17 C24 H24B 109.0 . . ?
H24A C24 H24B 107.8 . . ?
C26 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C26 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 C25 102.5(13) . . ?
C27 C26 H26A 111.3 . . ?
C25 C26 H26A 111.3 . . ?
C27 C26 H26B 111.3 . . ?
C25 C26 H26B 111.3 . . ?
H26A C26 H26B 109.2 . . ?
C28 C27 C26 110.4(13) . . ?
C28 C27 H27A 109.6 . . ?
C26 C27 H27A 109.6 . . ?
C28 C27 H27B 109.6 . . ?
C26 C27 H27B 109.6 . . ?
H27A C27 H27B 108.1 . . ?
C27 C28 C29 106.5(13) . . ?
C27 C28 H28A 110.4 . . ?
C29 C28 H28A 110.4 . . ?
C27 C28 H28B 110.4 . . ?
C29 C28 H28B 110.4 . . ?
H28A C28 H28B 108.6 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C17 B1 C16 126.49(18) . . ?
C17 B1 C21 111.62(17) . . ?
C16 B1 C21 121.52(18) . . ?
C2 N1 C6 119.58(15) . . ?
C2 N1 Fe1 125.87(12) . . ?
C6 N1 Fe1 114.51(11) . . ?
C7 N2 N3 106.31(14) . . ?
C7 N2 Fe1 115.15(12) . . ?
N3 N2 Fe1 138.42(11) . . ?
N2 N3 C9 111.17(14) . . ?
N2 N3 C14 117.29(14) . . ?
C9 N3 C14 131.54(16) . . ?
N2 Fe1 N1 78.10(6) . . ?
N2 Fe1 Cl1 115.02(4) . . ?
N1 Fe1 Cl1 109.51(4) . . ?
N2 Fe1 Cl2 107.70(4) . . ?
N1 Fe1 Cl2 111.79(4) . . ?
Cl1 Fe1 Cl2 125.05(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 -1.1(3) . . . . ?
C1 C2 C3 C4 178.85(18) . . . . ?
C2 C3 C4 C5 2.6(3) . . . . ?
C3 C4 C5 C6 -1.3(3) . . . . ?
C4 C5 C6 N1 -1.5(3) . . . . ?
C4 C5 C6 C7 179.60(16) . . . . ?
N1 C6 C7 N2 -2.8(2) . . . . ?
C5 C6 C7 N2 176.19(16) . . . . ?
N1 C6 C7 C8 -179.60(18) . . . . ?
C5 C6 C7 C8 -0.6(3) . . . . ?
N2 C7 C8 C9 -0.7(2) . . . . ?
C6 C7 C8 C9 176.29(18) . . . . ?
C7 C8 C9 N3 0.6(2) . . . . ?
C7 C8 C9 C10 -178.88(17) . . . . ?
N3 C9 C10 C12 -63.9(2) . . . . ?
C8 C9 C10 C12 115.5(2) . . . . ?
N3 C9 C10 C13 177.97(18) . . . . ?
C8 C9 C10 C13 -2.7(3) . . . . ?
N3 C9 C10 C11 60.1(3) . . . . ?
C8 C9 C10 C11 -120.5(2) . . . . ?
N3 C14 C15 C16 175.28(16) . . . . ?
C14 C15 C16 B1 175.67(18) . . . . ?
C24 C17 C18 C19 -113.7(3) . . . . ?
B1 C17 C18 C19 1.2(3) . . . . ?
C17 C18 C19 C20 51.8(3) . . . . ?
C18 C19 C20 C21 -51.8(3) . . . . ?
C19 C20 C21 C22 114.3(2) . . . . ?
C19 C20 C21 B1 -0.8(3) . . . . ?
C20 C21 C22 C23 -63.0(3) . . . . ?
B1 C21 C22 C23 56.7(2) . . . . ?
C21 C22 C23 C24 -52.2(3) . . . . ?
C22 C23 C24 C17 52.9(3) . . . . ?
C18 C17 C24 C23 61.7(3) . . . . ?
B1 C17 C24 C23 -58.0(3) . . . . ?
C25 C26 C27 C28 172.8(14) . . . . ?
C26 C27 C28 C29 169(2) . . . . ?
C24 C17 B1 C16 -105.1(2) . . . . ?
C18 C17 B1 C16 134.0(2) . . . . ?
C24 C17 B1 C21 68.1(2) . . . . ?
C18 C17 B1 C21 -52.9(3) . . . . ?
C15 C16 B1 C17 3.0(3) . . . . ?
C15 C16 B1 C21 -169.54(19) . . . . ?
C22 C21 B1 C17 -67.7(2) . . . . ?
C20 C21 B1 C17 52.6(3) . . . . ?
C22 C21 B1 C16 105.8(2) . . . . ?
C20 C21 B1 C16 -133.9(2) . . . . ?
C3 C2 N1 C6 -1.7(3) . . . . ?
C1 C2 N1 C6 178.40(16) . . . . ?
C3 C2 N1 Fe1 175.87(13) . . . . ?
C1 C2 N1 Fe1 -4.0(2) . . . . ?
C5 C6 N1 C2 3.0(3) . . . . ?
C7 C6 N1 C2 -178.00(15) . . . . ?
C5 C6 N1 Fe1 -174.83(13) . . . . ?
C7 C6 N1 Fe1 4.18(19) . . . . ?
C8 C7 N2 N3 0.51(19) . . . . ?
C6 C7 N2 N3 -176.97(14) . . . . ?
C8 C7 N2 Fe1 177.43(12) . . . . ?
C6 C7 N2 Fe1 0.0(2) . . . . ?
C7 N2 N3 C9 -0.14(19) . . . . ?
Fe1 N2 N3 C9 -175.95(13) . . . . ?
C7 N2 N3 C14 -179.30(14) . . . . ?
Fe1 N2 N3 C14 4.9(2) . . . . ?
C8 C9 N3 N2 -0.3(2) . . . . ?
C10 C9 N3 N2 179.19(16) . . . . ?
C8 C9 N3 C14 178.72(17) . . . . ?
C10 C9 N3 C14 -1.8(3) . . . . ?
C15 C14 N3 N2 72.4(2) . . . . ?
C15 C14 N3 C9 -106.6(2) . . . . ?

_refine_diff_density_max         0.439
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.051


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_JK4288_0m
_database_code_depnum_ccdc_archive 'CCDC 1941379'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller '
;Purdue University
United States of America
;
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C48 H76 B2 Br4 N8 Zn2, 0.374(C H2 Cl2)'
_chemical_formula_sum            'C48.37 H76.75 B2 Br4 Cl0.75 N8 Zn2'
_chemical_formula_weight         1268.96

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   14.0158(5)
_cell_length_b                   14.8791(6)
_cell_length_c                   15.8974(6)
_cell_angle_alpha                70.5598(17)
_cell_angle_beta                 69.5099(18)
_cell_angle_gamma                65.6987(17)
_cell_volume                     2760.31(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9883
_cell_measurement_theta_min      3.0429
_cell_measurement_theta_max      74.3179

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_F_000             1291
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    5.095
_shelx_estimated_absorpt_T_min   0.213
_shelx_estimated_absorpt_T_max   0.905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.508514
_exptl_absorpt_correction_T_max  0.753816
_exptl_absorpt_process_details   
;
TWINABS 2012/1: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.
(2015). J. Appl. Cryst. 48 3-10.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            54688
_diffrn_reflns_av_unetI/netI     0.1012
_diffrn_reflns_av_R_equivalents  0.0926
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.043
_diffrn_reflns_theta_max         74.825
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             21498
_reflns_number_gt                16450
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Apex3 v2017.3-0 (Bruker, 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev937 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
The crystal under investigation was found to be non-merohedrally 
twinned. The orientation matrices for the two components were 
identified using the program Cell_Now, with the two components 
being related by a 180 degree rotation around the real 
axis (-1 0 1). The two components were integrated using Saint and 
corrected for absorption using twinabs, resulting in the 
following statistics:

25979 data (9946 unique) involve domain 1 only, mean I/sigma 11.5
25959 data (9943 unique) involve domain 2 only, mean I/sigma 11.8
 2816 data (1612 unique) involve 2 domains, mean I/sigma 15.7

The exact twin matrix identified by the integration program was 
found to be: 

-0.27464 -0.00916 -0.76365
-0.00020 -0.99981 -0.00030
-1.21103  0.01618  0.27446

The structure was solved using direct methods with only the 
non-overlapping reflections of component 1. The structure was 
refined using the hklf 5 routine with all reflections of component 
1 (including the overlapping ones), resulting in a BASF value of 
0.492(1).

The Rint value given is for all reflections and is based on 
agreement between observed single and composite intensities 
and those calculated from refined unique intensities and twin 
fractions (TWINABS (Sheldrick, 2012)).

A partially occupied methylene chloride molecule is disordered 
around an inversion center over four positions (each two related 
to each other by inversion symmetry). All C-Cl distances were 
restrained to be similar to each other. Uij components of ADPs 
for disordered atoms closer to each other than 2.0 Angstrom were 
restrained to be similar. Subject to these conditions the 
occupancy rates refined to two times 0.179(12) and two times 
0.195(12), for a total occupancy of the site of 74.8%. No other 
solvate molecules are resolved for the site. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1016P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         21498
_refine_ls_number_parameters     642
_refine_ls_number_restraints     66
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0592
_refine_ls_wR_factor_ref         0.1907
_refine_ls_wR_factor_gt          0.1760
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.2163(5) 0.7190(4) -0.1246(4) 0.0418(13) Uani 1 1 d . . . . .
H1A H 0.215669 0.746913 -0.189672 0.063 Uiso 1 1 calc R U . . .
H1B H 0.228733 0.765483 -0.101353 0.063 Uiso 1 1 calc R U . . .
H1C H 0.146615 0.710061 -0.089172 0.063 Uiso 1 1 calc R U . . .
C2 C 0.3056(4) 0.6179(4) -0.1147(4) 0.0332(11) Uani 1 1 d . . . . .
C3 C 0.3760(5) 0.5783(4) -0.1893(4) 0.0374(12) Uani 1 1 d . . . . .
H3 H 0.368555 0.614299 -0.249689 0.045 Uiso 1 1 calc R U . . .
C4 C 0.4568(5) 0.4872(4) -0.1767(4) 0.0358(12) Uani 1 1 d . . . . .
H4 H 0.505664 0.459918 -0.228174 0.043 Uiso 1 1 calc R U . . .
C5 C 0.4667(4) 0.4348(4) -0.0878(4) 0.0305(11) Uani 1 1 d . . . . .
H5 H 0.522165 0.371495 -0.077129 0.037 Uiso 1 1 calc R U . . .
C6 C 0.3938(4) 0.4776(3) -0.0159(3) 0.0248(9) Uani 1 1 d . . . . .
C7 C 0.3927(4) 0.4273(3) 0.0811(3) 0.0244(9) Uani 1 1 d . . . . .
C8 C 0.4564(4) 0.3352(3) 0.1227(3) 0.0263(10) Uani 1 1 d . . . . .
H8 H 0.518327 0.288242 0.092641 0.032 Uiso 1 1 calc R U . . .
C9 C 0.4119(4) 0.3248(3) 0.2170(4) 0.0253(10) Uani 1 1 d . . . . .
C10 C 0.4443(5) 0.2334(4) 0.2934(4) 0.0340(12) Uani 1 1 d . . . . .
C11 C 0.3600(5) 0.1808(4) 0.3288(4) 0.0387(13) Uani 1 1 d . . . . .
H11A H 0.355202 0.160811 0.278013 0.058 Uiso 1 1 calc R U . . .
H11B H 0.289519 0.227326 0.354194 0.058 Uiso 1 1 calc R U . . .
H11C H 0.380950 0.120672 0.377068 0.058 Uiso 1 1 calc R U . . .
C12 C 0.5524(5) 0.1596(4) 0.2531(4) 0.0438(14) Uani 1 1 d . . . . .
H12A H 0.546383 0.142284 0.201209 0.066 Uiso 1 1 calc R U . . .
H12B H 0.571810 0.098042 0.300502 0.066 Uiso 1 1 calc R U . . .
H12C H 0.608391 0.191073 0.231558 0.066 Uiso 1 1 calc R U . . .
C13 C 0.4562(6) 0.2613(5) 0.3731(4) 0.0456(15) Uani 1 1 d . . . . .
H13A H 0.509134 0.296512 0.349343 0.068 Uiso 1 1 calc R U . . .
H13B H 0.480711 0.199640 0.418825 0.068 Uiso 1 1 calc R U . . .
H13C H 0.386192 0.305597 0.401899 0.068 Uiso 1 1 calc R U . . .
C14 C 0.2456(4) 0.4442(4) 0.3101(4) 0.0309(11) Uani 1 1 d . . . . .
H14A H 0.243909 0.384119 0.361280 0.037 Uiso 1 1 calc R U . . .
H14B H 0.173058 0.476759 0.297665 0.037 Uiso 1 1 calc R U . . .
C15 C 0.2699(4) 0.5178(4) 0.3401(4) 0.0306(11) Uani 1 1 d . . . . .
H15A H 0.270030 0.578857 0.289911 0.037 Uiso 1 1 calc R U . . .
H15B H 0.342447 0.485938 0.352527 0.037 Uiso 1 1 calc R U . . .
C16 C 0.1853(5) 0.5481(4) 0.4268(4) 0.0345(12) Uani 1 1 d . . . . .
H16A H 0.182063 0.485569 0.474180 0.041 Uiso 1 1 calc R U . . .
H16B H 0.113992 0.582314 0.411985 0.041 Uiso 1 1 calc R U . . .
C17 C 0.3230(5) 0.5855(4) 0.4885(4) 0.0416(13) Uani 1 1 d . . . . .
H17 H 0.377718 0.576401 0.428706 0.050 Uiso 1 1 calc R U . . .
C18 C 0.3408(6) 0.4822(5) 0.5570(5) 0.0570(18) Uani 1 1 d . . . . .
H18A H 0.344682 0.431913 0.526885 0.068 Uiso 1 1 calc R U . . .
H18B H 0.411513 0.461019 0.570935 0.068 Uiso 1 1 calc R U . . .
C19 C 0.2535(8) 0.4801(5) 0.6481(5) 0.070(2) Uani 1 1 d . . . . .
H19A H 0.268265 0.508100 0.688858 0.084 Uiso 1 1 calc R U . . .
H19B H 0.259762 0.408724 0.678508 0.084 Uiso 1 1 calc R U . . .
C20 C 0.1366(7) 0.5387(5) 0.6398(5) 0.061(2) Uani 1 1 d . . . . .
H20A H 0.090580 0.550663 0.701163 0.073 Uiso 1 1 calc R U . . .
H20B H 0.111707 0.495318 0.622699 0.073 Uiso 1 1 calc R U . . .
C21 C 0.1181(6) 0.6415(4) 0.5695(4) 0.0423(14) Uani 1 1 d . . . . .
H21 H 0.043182 0.666166 0.561441 0.051 Uiso 1 1 calc R U . . .
C22 C 0.1315(6) 0.7223(5) 0.6013(5) 0.0516(17) Uani 1 1 d . . . . .
H22A H 0.108026 0.788527 0.558849 0.062 Uiso 1 1 calc R U . . .
H22B H 0.082741 0.727783 0.663265 0.062 Uiso 1 1 calc R U . . .
C23 C 0.2452(7) 0.7016(6) 0.6053(6) 0.064(2) Uani 1 1 d . . . . .
H23A H 0.259217 0.649639 0.661819 0.077 Uiso 1 1 calc R U . . .
H23B H 0.249386 0.764202 0.610589 0.077 Uiso 1 1 calc R U . . .
C24 C 0.3351(6) 0.6654(5) 0.5224(5) 0.0534(17) Uani 1 1 d . . . . .
H24A H 0.405173 0.636855 0.539107 0.064 Uiso 1 1 calc R U . . .
H24B H 0.337483 0.724897 0.470724 0.064 Uiso 1 1 calc R U . . .
C25 C 0.7130(5) 0.7762(4) 0.1985(4) 0.0424(13) Uani 1 1 d . . . . .
H25A H 0.673728 0.734325 0.199510 0.064 Uiso 1 1 calc R U . . .
H25B H 0.693842 0.788922 0.259969 0.064 Uiso 1 1 calc R U . . .
H25C H 0.790934 0.740783 0.180388 0.064 Uiso 1 1 calc R U . . .
C26 C 0.6834(4) 0.8743(4) 0.1311(4) 0.0328(11) Uani 1 1 d . . . . .
C27 C 0.7581(5) 0.9095(4) 0.0574(4) 0.0392(13) Uani 1 1 d . . . . .
H27 H 0.832876 0.871147 0.048552 0.047 Uiso 1 1 calc R U . . .
C28 C 0.7241(5) 0.9992(4) -0.0022(4) 0.0387(12) Uani 1 1 d . . . . .
H28 H 0.775710 1.023035 -0.052198 0.046 Uiso 1 1 calc R U . . .
C29 C 0.6154(5) 1.0561(4) 0.0089(4) 0.0332(11) Uani 1 1 d . . . . .
H29 H 0.591212 1.118041 -0.033190 0.040 Uiso 1 1 calc R U . . .
C30 C 0.5433(4) 1.0192(4) 0.0839(4) 0.0272(10) Uani 1 1 d . . . . .
C31 C 0.4272(4) 1.0738(4) 0.1073(3) 0.0276(10) Uani 1 1 d . . . . .
C32 C 0.3620(4) 1.1668(4) 0.0691(4) 0.0290(10) Uani 1 1 d . . . . .
H32 H 0.383814 1.212376 0.014280 0.035 Uiso 1 1 calc R U . . .
C33 C 0.2584(4) 1.1810(4) 0.1262(4) 0.0300(11) Uani 1 1 d . . . . .
C34 C 0.1587(5) 1.2747(4) 0.1209(4) 0.0360(12) Uani 1 1 d . . . . .
C35 C 0.0588(5) 1.2519(4) 0.1271(5) 0.0410(13) Uani 1 1 d . . . . .
H35A H -0.003868 1.314196 0.127470 0.061 Uiso 1 1 calc R U . . .
H35B H 0.044727 1.201659 0.183869 0.061 Uiso 1 1 calc R U . . .
H35C H 0.071834 1.225367 0.073875 0.061 Uiso 1 1 calc R U . . .
C36 C 0.1360(5) 1.3267(4) 0.1981(5) 0.0463(15) Uani 1 1 d . . . . .
H36A H 0.201131 1.338839 0.194427 0.069 Uiso 1 1 calc R U . . .
H36B H 0.115482 1.283133 0.257962 0.069 Uiso 1 1 calc R U . . .
H36C H 0.076939 1.391325 0.191068 0.069 Uiso 1 1 calc R U . . .
C37 C 0.1825(5) 1.3477(4) 0.0280(5) 0.0454(15) Uani 1 1 d . . . . .
H37A H 0.199067 1.314995 -0.022112 0.068 Uiso 1 1 calc R U . . .
H37B H 0.244469 1.365605 0.023036 0.068 Uiso 1 1 calc R U . . .
H37C H 0.119121 1.409039 0.023721 0.068 Uiso 1 1 calc R U . . .
C38 C 0.1855(4) 1.0664(4) 0.2771(4) 0.0311(11) Uani 1 1 d . . . . .
H38A H 0.123370 1.127727 0.290323 0.037 Uiso 1 1 calc R U . . .
H38B H 0.218568 1.036418 0.330192 0.037 Uiso 1 1 calc R U . . .
C39 C 0.1441(4) 0.9911(4) 0.2682(4) 0.0290(10) Uani 1 1 d . . . . .
H39A H 0.205857 0.930279 0.253124 0.035 Uiso 1 1 calc R U . . .
H39B H 0.107657 1.021705 0.217062 0.035 Uiso 1 1 calc R U . . .
C40 C 0.0642(4) 0.9599(4) 0.3578(4) 0.0317(11) Uani 1 1 d . . . . .
H40A H 0.005071 1.022030 0.373296 0.038 Uiso 1 1 calc R U . . .
H40B H 0.102352 0.928877 0.407783 0.038 Uiso 1 1 calc R U . . .
C41 C -0.0797(5) 0.8570(4) 0.4512(4) 0.0361(12) Uani 1 1 d . . . . .
H41 H -0.047074 0.833248 0.504770 0.043 Uiso 1 1 calc R U . . .
C42 C -0.1162(5) 0.7735(4) 0.4488(5) 0.0442(14) Uani 1 1 d . . . . .
H42A H -0.055833 0.708641 0.455018 0.053 Uiso 1 1 calc R U . . .
H42B H -0.177019 0.767159 0.503176 0.053 Uiso 1 1 calc R U . . .
C43 C -0.1518(6) 0.7890(5) 0.3623(5) 0.0510(16) Uani 1 1 d . . . . .
H43A H -0.150836 0.723190 0.359290 0.061 Uiso 1 1 calc R U . . .
H43B H -0.227365 0.835592 0.368913 0.061 Uiso 1 1 calc R U . . .
C44 C -0.0825(5) 0.8312(5) 0.2712(5) 0.0422(13) Uani 1 1 d . . . . .
H44A H -0.123977 0.858456 0.223797 0.051 Uiso 1 1 calc R U . . .
H44B H -0.017328 0.774668 0.251775 0.051 Uiso 1 1 calc R U . . .
C45 C -0.0461(5) 0.9149(4) 0.2738(4) 0.0360(12) Uani 1 1 d . . . . .
H45 H 0.008066 0.928186 0.214628 0.043 Uiso 1 1 calc R U . . .
C46 C -0.1409(5) 1.0148(4) 0.2837(5) 0.0433(14) Uani 1 1 d . . . . .
H46A H -0.111087 1.068642 0.272801 0.052 Uiso 1 1 calc R U . . .
H46B H -0.179005 1.033580 0.235187 0.052 Uiso 1 1 calc R U . . .
C47 C -0.2234(5) 1.0115(5) 0.3773(5) 0.0461(15) Uani 1 1 d . . . . .
H47A H -0.271555 0.977251 0.378809 0.055 Uiso 1 1 calc R U . . .
H47B H -0.268496 1.081711 0.383136 0.055 Uiso 1 1 calc R U . . .
C48 C -0.1745(5) 0.9574(5) 0.4608(4) 0.0421(13) Uani 1 1 d . . . . .
H48A H -0.232297 0.943360 0.515445 0.050 Uiso 1 1 calc R U . . .
H48B H -0.148664 1.003870 0.472478 0.050 Uiso 1 1 calc R U . . .
C49 C 0.067(3) 0.983(2) -0.030(3) 0.052(6) Uani 0.179(12) 1 d D U P A -1
H49A H 0.121538 1.005021 -0.083495 0.062 Uiso 0.179(12) 1 calc R U P A -1
H49B H 0.104472 0.933949 0.017299 0.062 Uiso 0.179(12) 1 calc R U P A -1
Cl1 Cl 0.012(4) 0.926(4) -0.064(3) 0.048(5) Uani 0.179(12) 1 d D U P A -1
Cl2 Cl -0.021(2) 1.0830(18) 0.0121(16) 0.059(5) Uani 0.179(12) 1 d D U P A -1
C50 C 0.007(3) 1.047(2) -0.044(2) 0.052(5) Uani 0.195(12) 1 d D U P B -2
H50A H -0.056313 1.090582 -0.070380 0.062 Uiso 0.195(12) 1 calc R U P B -2
H50B H 0.070196 1.062738 -0.089039 0.062 Uiso 0.195(12) 1 calc R U P B -2
Cl3 Cl 0.024(3) 0.930(3) -0.044(3) 0.055(6) Uani 0.195(12) 1 d D U P B -2
Cl4 Cl -0.013(4) 1.086(4) 0.048(3) 0.051(7) Uani 0.195(12) 1 d D U P B -2
B1 B 0.2036(5) 0.6218(4) 0.4719(4) 0.0338(13) Uani 1 1 d . . . . .
B2 B 0.0101(5) 0.8814(4) 0.3575(4) 0.0313(12) Uani 1 1 d . . . . .
N1 N 0.3134(3) 0.5679(3) -0.0290(3) 0.0261(8) Uani 1 1 d . . . . .
N2 N 0.3135(3) 0.4735(3) 0.1454(3) 0.0244(8) Uani 1 1 d . . . . .
N3 N 0.3251(3) 0.4109(3) 0.2275(3) 0.0267(8) Uani 1 1 d . . . . .
N4 N 0.5772(3) 0.9297(3) 0.1436(3) 0.0269(8) Uani 1 1 d . . . . .
N5 N 0.3672(3) 1.0302(3) 0.1844(3) 0.0263(8) Uani 1 1 d . . . . .
N6 N 0.2649(4) 1.0962(3) 0.1951(3) 0.0283(9) Uani 1 1 d . . . . .
N7 N 0.1927(4) 0.7331(3) 0.3944(3) 0.0316(9) Uani 1 1 d . . . . .
H7A H 0.179891 0.780415 0.425055 0.038 Uiso 1 1 calc R U . . .
H7B H 0.258382 0.726969 0.353655 0.038 Uiso 1 1 calc R U . . .
N8 N 0.1121(3) 0.7739(3) 0.3410(3) 0.0296(9) Uani 1 1 d . . . . .
H8A H 0.082796 0.725451 0.352134 0.036 Uiso 1 1 calc R U . . .
H8B H 0.147516 0.783737 0.280362 0.036 Uiso 1 1 calc R U . . .
Zn1 Zn 0.21014(5) 0.61151(5) 0.09231(5) 0.02722(17) Uani 1 1 d . . . . .
Zn2 Zn 0.45486(6) 0.89329(5) 0.25297(5) 0.02773(17) Uani 1 1 d . . . . .
Br1 Br 0.03200(5) 0.62208(4) 0.11990(5) 0.04290(18) Uani 1 1 d . . . . .
Br2 Br 0.24045(5) 0.74826(4) 0.10989(4) 0.03599(16) Uani 1 1 d . . . . .
Br3 Br 0.46253(6) 0.88946(5) 0.39699(4) 0.0488(2) Uani 1 1 d . . . . .
Br4 Br 0.42536(5) 0.75834(4) 0.23073(4) 0.03714(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 1.511(8) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 N1 1.336(7) . ?
C2 C3 1.376(8) . ?
C3 C4 1.369(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.374(7) . ?
C5 H5 0.9500 . ?
C6 N1 1.360(6) . ?
C6 C7 1.471(7) . ?
C7 N2 1.340(6) . ?
C7 C8 1.384(7) . ?
C8 C9 1.389(7) . ?
C8 H8 0.9500 . ?
C9 N3 1.366(6) . ?
C9 C10 1.520(7) . ?
C10 C11 1.525(8) . ?
C10 C12 1.527(8) . ?
C10 C13 1.536(8) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 N3 1.471(6) . ?
C14 C15 1.520(7) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.529(7) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 B1 1.633(8) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.539(9) . ?
C17 C24 1.546(9) . ?
C17 B1 1.622(9) . ?
C17 H17 1.0000 . ?
C18 C19 1.536(12) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.536(12) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.548(9) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.547(9) . ?
C21 B1 1.625(9) . ?
C21 H21 1.0000 . ?
C22 C23 1.514(11) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.537(11) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.491(8) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 N4 1.351(7) . ?
C26 C27 1.388(8) . ?
C27 C28 1.363(9) . ?
C27 H27 0.9500 . ?
C28 C29 1.385(8) . ?
C28 H28 0.9500 . ?
C29 C30 1.386(8) . ?
C29 H29 0.9500 . ?
C30 N4 1.362(6) . ?
C30 C31 1.461(7) . ?
C31 N5 1.352(7) . ?
C31 C32 1.381(7) . ?
C32 C33 1.390(8) . ?
C32 H32 0.9500 . ?
C33 N6 1.362(7) . ?
C33 C34 1.518(7) . ?
C34 C37 1.536(9) . ?
C34 C35 1.536(8) . ?
C34 C36 1.536(9) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 N6 1.463(7) . ?
C38 C39 1.521(7) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 C40 1.539(7) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 B2 1.636(8) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 C42 1.540(8) . ?
C41 C48 1.548(8) . ?
C41 B2 1.624(8) . ?
C41 H41 1.0000 . ?
C42 C43 1.539(10) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 C44 1.532(10) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 C45 1.544(8) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 C46 1.544(8) . ?
C45 B2 1.616(9) . ?
C45 H45 1.0000 . ?
C46 C47 1.532(9) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 C48 1.533(9) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C49 Cl1 1.65(3) . ?
C49 Cl2 1.66(2) . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C50 Cl3 1.65(3) . ?
C50 Cl4 1.66(3) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
B1 N7 1.688(7) . ?
B2 N8 1.676(7) . ?
N1 Zn1 2.083(4) . ?
N2 N3 1.346(6) . ?
N2 Zn1 2.069(4) . ?
N4 Zn2 2.075(4) . ?
N5 N6 1.353(6) . ?
N5 Zn2 2.061(4) . ?
N7 N8 1.459(6) . ?
N7 H7A 0.9100 . ?
N7 H7B 0.9100 . ?
N8 H8A 0.9100 . ?
N8 H8B 0.9100 . ?
Zn1 Br1 2.3253(9) . ?
Zn1 Br2 2.3604(8) . ?
Zn2 Br3 2.3101(9) . ?
Zn2 Br4 2.3635(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 121.0(5) . . ?
N1 C2 C1 116.5(5) . . ?
C3 C2 C1 122.5(5) . . ?
C4 C3 C2 120.3(5) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.4(5) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 117.8(5) . . ?
C6 C5 H5 121.1 . . ?
C4 C5 H5 121.1 . . ?
N1 C6 C5 122.4(5) . . ?
N1 C6 C7 114.7(4) . . ?
C5 C6 C7 122.8(4) . . ?
N2 C7 C8 109.9(4) . . ?
N2 C7 C6 117.5(4) . . ?
C8 C7 C6 132.5(4) . . ?
C7 C8 C9 106.5(4) . . ?
C7 C8 H8 126.7 . . ?
C9 C8 H8 126.7 . . ?
N3 C9 C8 105.8(4) . . ?
N3 C9 C10 125.9(5) . . ?
C8 C9 C10 128.0(4) . . ?
C9 C10 C11 108.7(4) . . ?
C9 C10 C12 108.5(5) . . ?
C11 C10 C12 108.1(5) . . ?
C9 C10 C13 112.7(4) . . ?
C11 C10 C13 110.1(5) . . ?
C12 C10 C13 108.6(5) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C15 113.3(4) . . ?
N3 C14 H14A 108.9 . . ?
C15 C14 H14A 108.9 . . ?
N3 C14 H14B 108.9 . . ?
C15 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 C16 110.6(4) . . ?
C14 C15 H15A 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C15 C16 B1 116.9(5) . . ?
C15 C16 H16A 108.1 . . ?
B1 C16 H16A 108.1 . . ?
C15 C16 H16B 108.1 . . ?
B1 C16 H16B 108.1 . . ?
H16A C16 H16B 107.3 . . ?
C18 C17 C24 112.7(5) . . ?
C18 C17 B1 107.5(5) . . ?
C24 C17 B1 111.1(5) . . ?
C18 C17 H17 108.5 . . ?
C24 C17 H17 108.5 . . ?
B1 C17 H17 108.5 . . ?
C19 C18 C17 115.0(6) . . ?
C19 C18 H18A 108.5 . . ?
C17 C18 H18A 108.5 . . ?
C19 C18 H18B 108.5 . . ?
C17 C18 H18B 108.5 . . ?
H18A C18 H18B 107.5 . . ?
C18 C19 C20 115.5(6) . . ?
C18 C19 H19A 108.4 . . ?
C20 C19 H19A 108.4 . . ?
C18 C19 H19B 108.4 . . ?
C20 C19 H19B 108.4 . . ?
H19A C19 H19B 107.5 . . ?
C19 C20 C21 116.0(7) . . ?
C19 C20 H20A 108.3 . . ?
C21 C20 H20A 108.3 . . ?
C19 C20 H20B 108.3 . . ?
C21 C20 H20B 108.3 . . ?
H20A C20 H20B 107.4 . . ?
C22 C21 C20 112.3(5) . . ?
C22 C21 B1 111.0(5) . . ?
C20 C21 B1 107.4(5) . . ?
C22 C21 H21 108.7 . . ?
C20 C21 H21 108.7 . . ?
B1 C21 H21 108.7 . . ?
C23 C22 C21 114.8(6) . . ?
C23 C22 H22A 108.6 . . ?
C21 C22 H22A 108.6 . . ?
C23 C22 H22B 108.6 . . ?
C21 C22 H22B 108.6 . . ?
H22A C22 H22B 107.5 . . ?
C22 C23 C24 115.3(5) . . ?
C22 C23 H23A 108.4 . . ?
C24 C23 H23A 108.4 . . ?
C22 C23 H23B 108.4 . . ?
C24 C23 H23B 108.4 . . ?
H23A C23 H23B 107.5 . . ?
C23 C24 C17 115.3(6) . . ?
C23 C24 H24A 108.5 . . ?
C17 C24 H24A 108.5 . . ?
C23 C24 H24B 108.5 . . ?
C17 C24 H24B 108.5 . . ?
H24A C24 H24B 107.5 . . ?
C26 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C26 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N4 C26 C27 119.7(5) . . ?
N4 C26 C25 116.7(5) . . ?
C27 C26 C25 123.6(5) . . ?
C28 C27 C26 120.0(5) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C27 C28 C29 121.1(5) . . ?
C27 C28 H28 119.5 . . ?
C29 C28 H28 119.5 . . ?
C28 C29 C30 117.3(5) . . ?
C28 C29 H29 121.3 . . ?
C30 C29 H29 121.3 . . ?
N4 C30 C29 121.7(5) . . ?
N4 C30 C31 114.9(4) . . ?
C29 C30 C31 123.4(5) . . ?
N5 C31 C32 109.6(5) . . ?
N5 C31 C30 116.9(4) . . ?
C32 C31 C30 133.4(5) . . ?
C31 C32 C33 106.8(5) . . ?
C31 C32 H32 126.6 . . ?
C33 C32 H32 126.6 . . ?
N6 C33 C32 106.1(4) . . ?
N6 C33 C34 125.4(5) . . ?
C32 C33 C34 128.2(5) . . ?
C33 C34 C37 108.4(5) . . ?
C33 C34 C35 113.1(4) . . ?
C37 C34 C35 107.6(5) . . ?
C33 C34 C36 108.8(5) . . ?
C37 C34 C36 108.4(5) . . ?
C35 C34 C36 110.4(5) . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C34 C37 H37A 109.5 . . ?
C34 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C34 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
N6 C38 C39 114.0(4) . . ?
N6 C38 H38A 108.8 . . ?
C39 C38 H38A 108.8 . . ?
N6 C38 H38B 108.8 . . ?
C39 C38 H38B 108.8 . . ?
H38A C38 H38B 107.7 . . ?
C38 C39 C40 111.3(4) . . ?
C38 C39 H39A 109.4 . . ?
C40 C39 H39A 109.4 . . ?
C38 C39 H39B 109.4 . . ?
C40 C39 H39B 109.4 . . ?
H39A C39 H39B 108.0 . . ?
C39 C40 B2 116.8(4) . . ?
C39 C40 H40A 108.1 . . ?
B2 C40 H40A 108.1 . . ?
C39 C40 H40B 108.1 . . ?
B2 C40 H40B 108.1 . . ?
H40A C40 H40B 107.3 . . ?
C42 C41 C48 112.5(5) . . ?
C42 C41 B2 111.0(5) . . ?
C48 C41 B2 107.2(4) . . ?
C42 C41 H41 108.7 . . ?
C48 C41 H41 108.7 . . ?
B2 C41 H41 108.7 . . ?
C43 C42 C41 116.2(5) . . ?
C43 C42 H42A 108.2 . . ?
C41 C42 H42A 108.2 . . ?
C43 C42 H42B 108.2 . . ?
C41 C42 H42B 108.2 . . ?
H42A C42 H42B 107.4 . . ?
C44 C43 C42 115.1(5) . . ?
C44 C43 H43A 108.5 . . ?
C42 C43 H43A 108.5 . . ?
C44 C43 H43B 108.5 . . ?
C42 C43 H43B 108.5 . . ?
H43A C43 H43B 107.5 . . ?
C43 C44 C45 115.3(5) . . ?
C43 C44 H44A 108.4 . . ?
C45 C44 H44A 108.4 . . ?
C43 C44 H44B 108.4 . . ?
C45 C44 H44B 108.4 . . ?
H44A C44 H44B 107.5 . . ?
C46 C45 C44 112.3(5) . . ?
C46 C45 B2 107.9(4) . . ?
C44 C45 B2 111.8(5) . . ?
C46 C45 H45 108.2 . . ?
C44 C45 H45 108.2 . . ?
B2 C45 H45 108.2 . . ?
C47 C46 C45 114.9(5) . . ?
C47 C46 H46A 108.5 . . ?
C45 C46 H46A 108.5 . . ?
C47 C46 H46B 108.5 . . ?
C45 C46 H46B 108.5 . . ?
H46A C46 H46B 107.5 . . ?
C46 C47 C48 115.0(5) . . ?
C46 C47 H47A 108.5 . . ?
C48 C47 H47A 108.5 . . ?
C46 C47 H47B 108.5 . . ?
C48 C47 H47B 108.5 . . ?
H47A C47 H47B 107.5 . . ?
C47 C48 C41 115.1(5) . . ?
C47 C48 H48A 108.5 . . ?
C41 C48 H48A 108.5 . . ?
C47 C48 H48B 108.5 . . ?
C41 C48 H48B 108.5 . . ?
H48A C48 H48B 107.5 . . ?
Cl1 C49 Cl2 114(3) . . ?
Cl1 C49 H49A 108.8 . . ?
Cl2 C49 H49A 108.8 . . ?
Cl1 C49 H49B 108.8 . . ?
Cl2 C49 H49B 108.8 . . ?
H49A C49 H49B 107.7 . . ?
Cl3 C50 Cl4 125(3) . . ?
Cl3 C50 H50A 106.2 . . ?
Cl4 C50 H50A 106.2 . . ?
Cl3 C50 H50B 106.2 . . ?
Cl4 C50 H50B 106.2 . . ?
H50A C50 H50B 106.4 . . ?
C17 B1 C21 106.3(5) . . ?
C17 B1 C16 115.4(5) . . ?
C21 B1 C16 114.3(5) . . ?
C17 B1 N7 104.2(5) . . ?
C21 B1 N7 109.3(4) . . ?
C16 B1 N7 106.8(4) . . ?
C45 B2 C41 106.1(5) . . ?
C45 B2 C40 115.0(5) . . ?
C41 B2 C40 114.9(4) . . ?
C45 B2 N8 104.8(4) . . ?
C41 B2 N8 109.2(4) . . ?
C40 B2 N8 106.3(4) . . ?
C2 N1 C6 119.1(4) . . ?
C2 N1 Zn1 126.6(3) . . ?
C6 N1 Zn1 114.2(3) . . ?
C7 N2 N3 106.7(4) . . ?
C7 N2 Zn1 113.9(3) . . ?
N3 N2 Zn1 139.4(3) . . ?
N2 N3 C9 111.1(4) . . ?
N2 N3 C14 117.2(4) . . ?
C9 N3 C14 131.7(4) . . ?
C26 N4 C30 120.3(4) . . ?
C26 N4 Zn2 125.3(3) . . ?
C30 N4 Zn2 114.4(3) . . ?
C31 N5 N6 106.5(4) . . ?
C31 N5 Zn2 114.2(3) . . ?
N6 N5 Zn2 139.2(3) . . ?
N5 N6 C33 111.0(4) . . ?
N5 N6 C38 116.2(4) . . ?
C33 N6 C38 132.7(4) . . ?
N8 N7 B1 120.0(4) . . ?
N8 N7 H7A 107.3 . . ?
B1 N7 H7A 107.3 . . ?
N8 N7 H7B 107.3 . . ?
B1 N7 H7B 107.3 . . ?
H7A N7 H7B 106.9 . . ?
N7 N8 B2 119.0(4) . . ?
N7 N8 H8A 107.6 . . ?
B2 N8 H8A 107.6 . . ?
N7 N8 H8B 107.6 . . ?
B2 N8 H8B 107.6 . . ?
H8A N8 H8B 107.0 . . ?
N2 Zn1 N1 79.64(16) . . ?
N2 Zn1 Br1 116.35(11) . . ?
N1 Zn1 Br1 115.57(11) . . ?
N2 Zn1 Br2 111.95(11) . . ?
N1 Zn1 Br2 109.67(11) . . ?
Br1 Zn1 Br2 117.67(3) . . ?
N5 Zn2 N4 79.58(16) . . ?
N5 Zn2 Br3 115.89(12) . . ?
N4 Zn2 Br3 115.82(12) . . ?
N5 Zn2 Br4 110.79(11) . . ?
N4 Zn2 Br4 108.46(11) . . ?
Br3 Zn2 Br4 119.48(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 -1.0(8) . . . . ?
C1 C2 C3 C4 178.8(5) . . . . ?
C2 C3 C4 C5 0.3(8) . . . . ?
C3 C4 C5 C6 0.1(8) . . . . ?
C4 C5 C6 N1 0.2(7) . . . . ?
C4 C5 C6 C7 176.9(4) . . . . ?
N1 C6 C7 N2 1.1(6) . . . . ?
C5 C6 C7 N2 -175.8(4) . . . . ?
N1 C6 C7 C8 177.3(5) . . . . ?
C5 C6 C7 C8 0.4(8) . . . . ?
N2 C7 C8 C9 1.0(5) . . . . ?
C6 C7 C8 C9 -175.4(5) . . . . ?
C7 C8 C9 N3 -0.6(5) . . . . ?
C7 C8 C9 C10 173.7(5) . . . . ?
N3 C9 C10 C11 68.7(6) . . . . ?
C8 C9 C10 C11 -104.5(6) . . . . ?
N3 C9 C10 C12 -174.0(5) . . . . ?
C8 C9 C10 C12 12.8(7) . . . . ?
N3 C9 C10 C13 -53.6(7) . . . . ?
C8 C9 C10 C13 133.1(6) . . . . ?
N3 C14 C15 C16 -179.2(4) . . . . ?
C14 C15 C16 B1 176.4(5) . . . . ?
C24 C17 C18 C19 68.0(8) . . . . ?
B1 C17 C18 C19 -54.7(8) . . . . ?
C17 C18 C19 C20 41.5(10) . . . . ?
C18 C19 C20 C21 -40.3(9) . . . . ?
C19 C20 C21 C22 -70.2(8) . . . . ?
C19 C20 C21 B1 52.1(8) . . . . ?
C20 C21 C22 C23 66.8(8) . . . . ?
B1 C21 C22 C23 -53.4(8) . . . . ?
C21 C22 C23 C24 44.0(9) . . . . ?
C22 C23 C24 C17 -43.1(9) . . . . ?
C18 C17 C24 C23 -69.5(8) . . . . ?
B1 C17 C24 C23 51.2(7) . . . . ?
N4 C26 C27 C28 -0.5(8) . . . . ?
C25 C26 C27 C28 178.7(6) . . . . ?
C26 C27 C28 C29 -0.4(9) . . . . ?
C27 C28 C29 C30 1.2(8) . . . . ?
C28 C29 C30 N4 -1.1(7) . . . . ?
C28 C29 C30 C31 176.3(5) . . . . ?
N4 C30 C31 N5 0.0(6) . . . . ?
C29 C30 C31 N5 -177.6(5) . . . . ?
N4 C30 C31 C32 176.2(5) . . . . ?
C29 C30 C31 C32 -1.4(9) . . . . ?
N5 C31 C32 C33 1.0(6) . . . . ?
C30 C31 C32 C33 -175.5(5) . . . . ?
C31 C32 C33 N6 -0.8(5) . . . . ?
C31 C32 C33 C34 173.4(5) . . . . ?
N6 C33 C34 C37 -174.4(5) . . . . ?
C32 C33 C34 C37 12.4(7) . . . . ?
N6 C33 C34 C35 -55.2(7) . . . . ?
C32 C33 C34 C35 131.6(6) . . . . ?
N6 C33 C34 C36 67.9(6) . . . . ?
C32 C33 C34 C36 -105.3(6) . . . . ?
N6 C38 C39 C40 177.8(4) . . . . ?
C38 C39 C40 B2 178.3(4) . . . . ?
C48 C41 C42 C43 69.1(7) . . . . ?
B2 C41 C42 C43 -51.0(7) . . . . ?
C41 C42 C43 C44 40.6(8) . . . . ?
C42 C43 C44 C45 -40.3(7) . . . . ?
C43 C44 C45 C46 -70.0(7) . . . . ?
C43 C44 C45 B2 51.5(7) . . . . ?
C44 C45 C46 C47 69.2(7) . . . . ?
B2 C45 C46 C47 -54.5(7) . . . . ?
C45 C46 C47 C48 43.0(7) . . . . ?
C46 C47 C48 C41 -43.4(7) . . . . ?
C42 C41 C48 C47 -67.6(7) . . . . ?
B2 C41 C48 C47 54.6(6) . . . . ?
C18 C17 B1 C21 66.0(6) . . . . ?
C24 C17 B1 C21 -57.7(6) . . . . ?
C18 C17 B1 C16 -61.8(7) . . . . ?
C24 C17 B1 C16 174.5(5) . . . . ?
C18 C17 B1 N7 -178.5(5) . . . . ?
C24 C17 B1 N7 57.8(6) . . . . ?
C22 C21 B1 C17 58.8(6) . . . . ?
C20 C21 B1 C17 -64.3(6) . . . . ?
C22 C21 B1 C16 -172.7(5) . . . . ?
C20 C21 B1 C16 64.2(7) . . . . ?
C22 C21 B1 N7 -53.2(6) . . . . ?
C20 C21 B1 N7 -176.2(5) . . . . ?
C15 C16 B1 C17 -50.2(7) . . . . ?
C15 C16 B1 C21 -173.9(5) . . . . ?
C15 C16 B1 N7 65.0(6) . . . . ?
C46 C45 B2 C41 65.1(6) . . . . ?
C44 C45 B2 C41 -58.9(6) . . . . ?
C46 C45 B2 C40 -63.1(6) . . . . ?
C44 C45 B2 C40 172.9(5) . . . . ?
C46 C45 B2 N8 -179.4(4) . . . . ?
C44 C45 B2 N8 56.6(6) . . . . ?
C42 C41 B2 C45 58.3(6) . . . . ?
C48 C41 B2 C45 -64.9(5) . . . . ?
C42 C41 B2 C40 -173.4(5) . . . . ?
C48 C41 B2 C40 63.4(6) . . . . ?
C42 C41 B2 N8 -54.2(6) . . . . ?
C48 C41 B2 N8 -177.4(4) . . . . ?
C39 C40 B2 C45 -52.3(6) . . . . ?
C39 C40 B2 C41 -175.9(4) . . . . ?
C39 C40 B2 N8 63.2(6) . . . . ?
C3 C2 N1 C6 1.3(7) . . . . ?
C1 C2 N1 C6 -178.5(4) . . . . ?
C3 C2 N1 Zn1 -176.5(4) . . . . ?
C1 C2 N1 Zn1 3.7(7) . . . . ?
C5 C6 N1 C2 -0.9(7) . . . . ?
C7 C6 N1 C2 -177.9(4) . . . . ?
C5 C6 N1 Zn1 177.2(4) . . . . ?
C7 C6 N1 Zn1 0.2(5) . . . . ?
C8 C7 N2 N3 -0.9(5) . . . . ?
C6 C7 N2 N3 176.1(4) . . . . ?
C8 C7 N2 Zn1 -178.9(3) . . . . ?
C6 C7 N2 Zn1 -1.9(5) . . . . ?
C7 N2 N3 C9 0.6(5) . . . . ?
Zn1 N2 N3 C9 177.7(4) . . . . ?
C7 N2 N3 C14 -179.0(4) . . . . ?
Zn1 N2 N3 C14 -1.8(7) . . . . ?
C8 C9 N3 N2 0.0(5) . . . . ?
C10 C9 N3 N2 -174.4(4) . . . . ?
C8 C9 N3 C14 179.5(5) . . . . ?
C10 C9 N3 C14 5.0(8) . . . . ?
C15 C14 N3 N2 -81.1(6) . . . . ?
C15 C14 N3 C9 99.5(6) . . . . ?
C27 C26 N4 C30 0.7(7) . . . . ?
C25 C26 N4 C30 -178.6(5) . . . . ?
C27 C26 N4 Zn2 -176.7(4) . . . . ?
C25 C26 N4 Zn2 4.0(7) . . . . ?
C29 C30 N4 C26 0.1(7) . . . . ?
C31 C30 N4 C26 -177.5(4) . . . . ?
C29 C30 N4 Zn2 177.8(4) . . . . ?
C31 C30 N4 Zn2 0.2(5) . . . . ?
C32 C31 N5 N6 -0.7(5) . . . . ?
C30 C31 N5 N6 176.4(4) . . . . ?
C32 C31 N5 Zn2 -177.2(3) . . . . ?
C30 C31 N5 Zn2 -0.1(5) . . . . ?
C31 N5 N6 C33 0.2(5) . . . . ?
Zn2 N5 N6 C33 175.3(4) . . . . ?
C31 N5 N6 C38 -177.7(4) . . . . ?
Zn2 N5 N6 C38 -2.7(7) . . . . ?
C32 C33 N6 N5 0.4(5) . . . . ?
C34 C33 N6 N5 -174.0(4) . . . . ?
C32 C33 N6 C38 177.9(5) . . . . ?
C34 C33 N6 C38 3.5(8) . . . . ?
C39 C38 N6 N5 -79.4(5) . . . . ?
C39 C38 N6 C33 103.2(6) . . . . ?
C17 B1 N7 N8 161.0(4) . . . . ?
C21 B1 N7 N8 -85.7(6) . . . . ?
C16 B1 N7 N8 38.4(6) . . . . ?
B1 N7 N8 B2 114.1(5) . . . . ?
C45 B2 N8 N7 168.4(4) . . . . ?
C41 B2 N8 N7 -78.3(5) . . . . ?
C40 B2 N8 N7 46.2(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N7 H7B Br4 0.91 2.57 3.459(5) 165.6 . yes
N8 H8B Br2 0.91 2.69 3.553(4) 158.7 . yes

_refine_diff_density_max         1.404
_refine_diff_density_min         -1.399
_refine_diff_density_rms         0.136


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
