# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_cu_12hp_co6_0ma
_database_code_depnum_ccdc_archive 'CCDC 1062600'
_audit_update_record             
;
2015-04-30 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H19 Br2 Fe N3 Ni'
_chemical_formula_sum            'C19 H19 Br2 Fe N3 Ni'
_chemical_formula_weight         563.75

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'
Ni Ni -3.0029 0.5091 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   14.1412(4)
_cell_length_b                   9.6921(3)
_cell_length_c                   13.6154(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.2300(10)
_cell_angle_gamma                90.00
_cell_volume                     1863.13(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9846
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      65.78

_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    2.010
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1112
_exptl_absorpt_coefficient_mu    12.581
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1522
_exptl_absorpt_correction_T_max  0.5719
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'Incoatec Quazar Multilayer Mirror'
_diffrn_measurement_device_type  'Bruker APEX DUO 4K-CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.4
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            25575
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.13
_diffrn_reflns_theta_max         66.50
_reflns_number_total             3170
_reflns_number_gt                3088
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Apex2 (Bruker, 2011)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT and XPREP (Bruker, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0270P)²+1.8295P] 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_number_reflns         3170
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0214
_refine_ls_R_factor_gt           0.0208
_refine_ls_wR_factor_ref         0.0540
_refine_ls_wR_factor_gt          0.0535
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.484575(16) 0.90754(3) 0.669463(17) 0.02350(8) Uani 1 1 d . . .
Br2 Br 0.238853(16) 1.11408(2) 0.669336(17) 0.02126(8) Uani 1 1 d . . .
Fe1 Fe 0.05750(2) 0.74188(3) 0.59949(2) 0.01435(10) Uani 1 1 d . . .
Ni1 Ni 0.33430(2) 0.93351(4) 0.73624(3) 0.01586(10) Uani 1 1 d . . .
N1 N 0.35803(12) 0.98546(19) 0.87766(13) 0.0162(4) Uani 1 1 d . . .
N2 N 0.33277(12) 0.68313(18) 0.85281(13) 0.0154(4) Uani 1 1 d . . .
N3 N 0.29850(12) 0.73849(18) 0.76603(13) 0.0143(4) Uani 1 1 d . . .
C1 C 0.34240(16) 1.1155(2) 0.90709(17) 0.0201(5) Uani 1 1 d . . .
H1 H 0.3237 1.1825 0.8589 0.024 Uiso 1 1 calc R . .
C2 C 0.35229(16) 1.1557(2) 1.00399(17) 0.0226(5) Uani 1 1 d . . .
H2 H 0.3412 1.2487 1.0221 0.027 Uiso 1 1 calc R . .
C3 C 0.37862(15) 1.0584(2) 1.07463(17) 0.0209(5) Uani 1 1 d . . .
H3 H 0.3839 1.0829 1.1423 0.025 Uiso 1 1 calc R . .
C4 C 0.39708(15) 0.9252(2) 1.04535(16) 0.0181(5) Uani 1 1 d . . .
H4 H 0.4169 0.8575 1.0926 0.022 Uiso 1 1 calc R . .
C5 C 0.38640(14) 0.8911(2) 0.94631(16) 0.0157(4) Uani 1 1 d . . .
C6 C 0.41042(15) 0.7494(2) 0.90984(17) 0.0169(5) Uani 1 1 d . . .
H6A H 0.4656 0.7565 0.8686 0.020 Uiso 1 1 calc R . .
H6B H 0.4290 0.6903 0.9670 0.020 Uiso 1 1 calc R . .
C7 C 0.29596(15) 0.5574(2) 0.86673(17) 0.0177(5) Uani 1 1 d . . .
H7 H 0.3099 0.4989 0.9216 0.021 Uiso 1 1 calc R . .
C8 C 0.23498(15) 0.5284(2) 0.78801(16) 0.0180(4) Uani 1 1 d . . .
H8 H 0.1981 0.4473 0.7776 0.022 Uiso 1 1 calc R . .
C9 C 0.23823(14) 0.6437(2) 0.72553(16) 0.0153(4) Uani 1 1 d . . .
C10 C 0.18910(14) 0.6604(2) 0.62953(16) 0.0157(4) Uani 1 1 d . . .
C11 C 0.19378(15) 0.7727(2) 0.56164(16) 0.0176(5) Uani 1 1 d . . .
H11 H 0.2295 0.8550 0.5719 0.021 Uiso 1 1 calc R . .
C12 C 0.13557(15) 0.7397(2) 0.47610(17) 0.0189(5) Uani 1 1 d . . .
H12 H 0.1257 0.7961 0.4194 0.023 Uiso 1 1 calc R . .
C13 C 0.09489(16) 0.6080(2) 0.49037(17) 0.0199(5) Uani 1 1 d . . .
H13 H 0.0529 0.5611 0.4448 0.024 Uiso 1 1 calc R . .
C14 C 0.12756(15) 0.5582(2) 0.58434(17) 0.0183(5) Uani 1 1 d . . .
H14 H 0.1115 0.4722 0.6124 0.022 Uiso 1 1 calc R . .
C15 C -0.00688(17) 0.9280(2) 0.61855(19) 0.0254(5) Uani 1 1 d . . .
H15 H 0.0120 1.0132 0.5913 0.030 Uiso 1 1 calc R . .
C16 C -0.07256(17) 0.8330(3) 0.57380(18) 0.0288(6) Uani 1 1 d . . .
H16 H -0.1057 0.8430 0.5115 0.035 Uiso 1 1 calc R . .
C17 C -0.07950(17) 0.7202(3) 0.6398(2) 0.0284(6) Uani 1 1 d . . .
H17 H -0.1182 0.6408 0.6292 0.034 Uiso 1 1 calc R . .
C18 C -0.01894(17) 0.7464(2) 0.72343(18) 0.0230(5) Uani 1 1 d . . .
H18 H -0.0098 0.6877 0.7791 0.028 Uiso 1 1 calc R . .
C19 C 0.02542(17) 0.8736(2) 0.71059(17) 0.0227(5) Uani 1 1 d . . .
H19 H 0.0697 0.9161 0.7561 0.027 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Ni1 2.3715(4) . ?
Br2 Ni1 2.3614(4) . ?
Fe1 C10 2.041(2) . ?
Fe1 C15 2.044(2) . ?
Fe1 C11 2.045(2) . ?
Fe1 C19 2.050(2) . ?
Fe1 C16 2.053(2) . ?
Fe1 C14 2.053(2) . ?
Fe1 C17 2.054(2) . ?
Fe1 C18 2.055(2) . ?
Fe1 C12 2.062(2) . ?
Fe1 C13 2.064(2) . ?
Ni1 N1 2.0002(18) . ?
Ni1 N3 2.0041(18) . ?
N1 C1 1.345(3) . ?
N1 C5 1.352(3) . ?
N2 C7 1.343(3) . ?
N2 N3 1.362(3) . ?
N2 C6 1.458(3) . ?
N3 C9 1.350(3) . ?
C1 C2 1.375(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.383(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.381(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.506(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.366(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.406(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.454(3) . ?
C10 C11 1.432(3) . ?
C10 C14 1.434(3) . ?
C11 C12 1.424(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.418(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.420(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C19 1.412(4) . ?
C15 C16 1.420(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.422(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.409(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.398(3) . ?
C18 H18 0.9500 . ?
C19 H19 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
C10 Fe1 C15 136.34(10) . . ?
C10 Fe1 C11 41.03(9) . . ?
C15 Fe1 C11 109.62(10) . . ?
C10 Fe1 C19 109.28(9) . . ?
C15 Fe1 C19 40.35(10) . . ?
C11 Fe1 C19 110.23(9) . . ?
C10 Fe1 C16 176.86(10) . . ?
C15 Fe1 C16 40.57(11) . . ?
C11 Fe1 C16 137.93(10) . . ?
C19 Fe1 C16 67.93(10) . . ?
C10 Fe1 C14 41.01(8) . . ?
C15 Fe1 C14 177.31(10) . . ?
C11 Fe1 C14 68.57(9) . . ?
C19 Fe1 C14 137.92(10) . . ?
C16 Fe1 C14 142.08(10) . . ?
C10 Fe1 C17 140.34(10) . . ?
C15 Fe1 C17 67.85(10) . . ?
C11 Fe1 C17 177.35(9) . . ?
C19 Fe1 C17 67.38(10) . . ?
C16 Fe1 C17 40.53(11) . . ?
C14 Fe1 C17 113.93(10) . . ?
C10 Fe1 C18 111.06(9) . . ?
C15 Fe1 C18 67.56(10) . . ?
C11 Fe1 C18 138.64(10) . . ?
C19 Fe1 C18 39.84(10) . . ?
C16 Fe1 C18 67.85(10) . . ?
C14 Fe1 C18 112.34(9) . . ?
C17 Fe1 C18 40.12(10) . . ?
C10 Fe1 C12 68.62(9) . . ?
C15 Fe1 C12 112.04(10) . . ?
C11 Fe1 C12 40.59(9) . . ?
C19 Fe1 C12 139.35(10) . . ?
C16 Fe1 C12 112.42(10) . . ?
C14 Fe1 C12 68.02(9) . . ?
C17 Fe1 C12 140.62(10) . . ?
C18 Fe1 C12 179.10(10) . . ?
C10 Fe1 C13 68.50(9) . . ?
C15 Fe1 C13 141.29(10) . . ?
C11 Fe1 C13 68.11(9) . . ?
C19 Fe1 C13 177.77(9) . . ?
C16 Fe1 C13 114.30(10) . . ?
C14 Fe1 C13 40.36(9) . . ?
C17 Fe1 C13 114.31(10) . . ?
C18 Fe1 C13 140.59(9) . . ?
C12 Fe1 C13 40.20(9) . . ?
N1 Ni1 N3 94.20(7) . . ?
N1 Ni1 Br2 104.24(5) . . ?
N3 Ni1 Br2 129.17(5) . . ?
N1 Ni1 Br1 106.88(5) . . ?
N3 Ni1 Br1 102.68(5) . . ?
Br2 Ni1 Br1 115.837(17) . . ?
C1 N1 C5 118.37(19) . . ?
C1 N1 Ni1 120.09(15) . . ?
C5 N1 Ni1 121.49(15) . . ?
C7 N2 N3 110.99(17) . . ?
C7 N2 C6 127.66(18) . . ?
N3 N2 C6 120.61(17) . . ?
C9 N3 N2 105.77(17) . . ?
C9 N3 Ni1 136.09(15) . . ?
N2 N3 Ni1 117.75(13) . . ?
N1 C1 C2 122.8(2) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C1 C2 C3 118.9(2) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 119.0(2) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 119.4(2) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 121.5(2) . . ?
N1 C5 C6 116.91(19) . . ?
C4 C5 C6 121.5(2) . . ?
N2 C6 C5 113.59(18) . . ?
N2 C6 H6A 108.8 . . ?
C5 C6 H6A 108.8 . . ?
N2 C6 H6B 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
N2 C7 C8 108.0(2) . . ?
N2 C7 H7 126.0 . . ?
C8 C7 H7 126.0 . . ?
C7 C8 C9 105.69(19) . . ?
C7 C8 H8 127.2 . . ?
C9 C8 H8 127.2 . . ?
N3 C9 C8 109.58(19) . . ?
N3 C9 C10 123.34(19) . . ?
C8 C9 C10 127.0(2) . . ?
C11 C10 C14 107.30(19) . . ?
C11 C10 C9 128.90(19) . . ?
C14 C10 C9 123.8(2) . . ?
C11 C10 Fe1 69.61(12) . . ?
C14 C10 Fe1 69.94(12) . . ?
C9 C10 Fe1 127.39(15) . . ?
C12 C11 C10 108.13(19) . . ?
C12 C11 Fe1 70.34(12) . . ?
C10 C11 Fe1 69.36(12) . . ?
C12 C11 H11 125.9 . . ?
C10 C11 H11 125.9 . . ?
Fe1 C11 H11 125.9 . . ?
C13 C12 C11 108.1(2) . . ?
C13 C12 Fe1 69.97(13) . . ?
C11 C12 Fe1 69.07(13) . . ?
C13 C12 H12 125.9 . . ?
C11 C12 H12 125.9 . . ?
Fe1 C12 H12 126.6 . . ?
C12 C13 C14 108.4(2) . . ?
C12 C13 Fe1 69.82(13) . . ?
C14 C13 Fe1 69.44(12) . . ?
C12 C13 H13 125.8 . . ?
C14 C13 H13 125.8 . . ?
Fe1 C13 H13 126.5 . . ?
C13 C14 C10 108.1(2) . . ?
C13 C14 Fe1 70.20(13) . . ?
C10 C14 Fe1 69.05(12) . . ?
C13 C14 H14 126.0 . . ?
C10 C14 H14 126.0 . . ?
Fe1 C14 H14 126.4 . . ?
C19 C15 C16 108.0(2) . . ?
C19 C15 Fe1 70.05(13) . . ?
C16 C15 Fe1 70.05(14) . . ?
C19 C15 H15 126.0 . . ?
C16 C15 H15 126.0 . . ?
Fe1 C15 H15 125.5 . . ?
C15 C16 C17 107.1(2) . . ?
C15 C16 Fe1 69.38(13) . . ?
C17 C16 Fe1 69.78(13) . . ?
C15 C16 H16 126.4 . . ?
C17 C16 H16 126.4 . . ?
Fe1 C16 H16 126.0 . . ?
C18 C17 C16 108.1(2) . . ?
C18 C17 Fe1 70.00(14) . . ?
C16 C17 Fe1 69.69(14) . . ?
C18 C17 H17 125.9 . . ?
C16 C17 H17 125.9 . . ?
Fe1 C17 H17 125.9 . . ?
C19 C18 C17 108.3(2) . . ?
C19 C18 Fe1 69.87(13) . . ?
C17 C18 Fe1 69.88(14) . . ?
C19 C18 H18 125.8 . . ?
C17 C18 H18 125.8 . . ?
Fe1 C18 H18 126.0 . . ?
C18 C19 C15 108.4(2) . . ?
C18 C19 Fe1 70.30(14) . . ?
C15 C19 Fe1 69.60(13) . . ?
C18 C19 H19 125.8 . . ?
C15 C19 H19 125.8 . . ?
Fe1 C19 H19 125.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 Ni1 N1 C1 -148.96(17) . . . . ?
Br2 Ni1 N1 C1 -16.74(17) . . . . ?
Br1 Ni1 N1 C1 106.42(16) . . . . ?
N3 Ni1 N1 C5 28.50(17) . . . . ?
Br2 Ni1 N1 C5 160.73(15) . . . . ?
Br1 Ni1 N1 C5 -76.12(16) . . . . ?
C7 N2 N3 C9 0.3(2) . . . . ?
C6 N2 N3 C9 171.16(18) . . . . ?
C7 N2 N3 Ni1 174.21(14) . . . . ?
C6 N2 N3 Ni1 -14.9(2) . . . . ?
N1 Ni1 N3 C9 146.9(2) . . . . ?
Br2 Ni1 N3 C9 34.7(2) . . . . ?
Br1 Ni1 N3 C9 -104.7(2) . . . . ?
N1 Ni1 N3 N2 -24.62(15) . . . . ?
Br2 Ni1 N3 N2 -136.83(12) . . . . ?
Br1 Ni1 N3 N2 83.75(14) . . . . ?
C5 N1 C1 C2 -1.3(3) . . . . ?
Ni1 N1 C1 C2 176.27(17) . . . . ?
N1 C1 C2 C3 -0.6(3) . . . . ?
C1 C2 C3 C4 2.1(3) . . . . ?
C2 C3 C4 C5 -1.7(3) . . . . ?
C1 N1 C5 C4 1.6(3) . . . . ?
Ni1 N1 C5 C4 -175.86(15) . . . . ?
C1 N1 C5 C6 -175.45(19) . . . . ?
Ni1 N1 C5 C6 7.0(3) . . . . ?
C3 C4 C5 N1 -0.2(3) . . . . ?
C3 C4 C5 C6 176.8(2) . . . . ?
C7 N2 C6 C5 -127.4(2) . . . . ?
N3 N2 C6 C5 63.4(3) . . . . ?
N1 C5 C6 N2 -57.7(3) . . . . ?
C4 C5 C6 N2 125.2(2) . . . . ?
N3 N2 C7 C8 -0.6(2) . . . . ?
C6 N2 C7 C8 -170.7(2) . . . . ?
N2 C7 C8 C9 0.6(2) . . . . ?
N2 N3 C9 C8 0.1(2) . . . . ?
Ni1 N3 C9 C8 -172.11(16) . . . . ?
N2 N3 C9 C10 -177.35(18) . . . . ?
Ni1 N3 C9 C10 10.4(3) . . . . ?
C7 C8 C9 N3 -0.5(2) . . . . ?
C7 C8 C9 C10 176.9(2) . . . . ?
N3 C9 C10 C11 0.3(3) . . . . ?
C8 C9 C10 C11 -176.8(2) . . . . ?
N3 C9 C10 C14 177.7(2) . . . . ?
C8 C9 C10 C14 0.7(3) . . . . ?
N3 C9 C10 Fe1 -92.8(2) . . . . ?
C8 C9 C10 Fe1 90.2(3) . . . . ?
C15 Fe1 C10 C11 -62.40(18) . . . . ?
C19 Fe1 C10 C11 -98.99(14) . . . . ?
C16 Fe1 C10 C11 -72.3(18) . . . . ?
C14 Fe1 C10 C11 118.26(18) . . . . ?
C17 Fe1 C10 C11 -176.48(15) . . . . ?
C18 Fe1 C10 C11 -141.51(13) . . . . ?
C12 Fe1 C10 C11 37.59(13) . . . . ?
C13 Fe1 C10 C11 80.92(14) . . . . ?
C15 Fe1 C10 C14 179.34(14) . . . . ?
C11 Fe1 C10 C14 -118.26(18) . . . . ?
C19 Fe1 C10 C14 142.76(14) . . . . ?
C16 Fe1 C10 C14 169.5(18) . . . . ?
C17 Fe1 C10 C14 65.26(19) . . . . ?
C18 Fe1 C10 C14 100.24(14) . . . . ?
C12 Fe1 C10 C14 -80.67(14) . . . . ?
C13 Fe1 C10 C14 -37.33(13) . . . . ?
C15 Fe1 C10 C9 61.6(2) . . . . ?
C11 Fe1 C10 C9 124.0(2) . . . . ?
C19 Fe1 C10 C9 25.0(2) . . . . ?
C16 Fe1 C10 C9 51.7(19) . . . . ?
C14 Fe1 C10 C9 -117.7(2) . . . . ?
C17 Fe1 C10 C9 -52.5(3) . . . . ?
C18 Fe1 C10 C9 -17.5(2) . . . . ?
C12 Fe1 C10 C9 161.6(2) . . . . ?
C13 Fe1 C10 C9 -155.1(2) . . . . ?
C14 C10 C11 C12 0.2(2) . . . . ?
C9 C10 C11 C12 177.9(2) . . . . ?
Fe1 C10 C11 C12 -59.89(15) . . . . ?
C14 C10 C11 Fe1 60.07(14) . . . . ?
C9 C10 C11 Fe1 -122.2(2) . . . . ?
C10 Fe1 C11 C12 119.19(19) . . . . ?
C15 Fe1 C11 C12 -101.32(15) . . . . ?
C19 Fe1 C11 C12 -144.36(14) . . . . ?
C16 Fe1 C11 C12 -65.28(19) . . . . ?
C14 Fe1 C11 C12 80.81(14) . . . . ?
C17 Fe1 C11 C12 -119(2) . . . . ?
C18 Fe1 C11 C12 -179.29(14) . . . . ?
C13 Fe1 C11 C12 37.23(14) . . . . ?
C15 Fe1 C11 C10 139.49(13) . . . . ?
C19 Fe1 C11 C10 96.45(14) . . . . ?
C16 Fe1 C11 C10 175.53(14) . . . . ?
C14 Fe1 C11 C10 -38.38(13) . . . . ?
C17 Fe1 C11 C10 122(2) . . . . ?
C18 Fe1 C11 C10 61.52(18) . . . . ?
C12 Fe1 C11 C10 -119.19(19) . . . . ?
C13 Fe1 C11 C10 -81.96(14) . . . . ?
C10 C11 C12 C13 0.0(2) . . . . ?
Fe1 C11 C12 C13 -59.29(15) . . . . ?
C10 C11 C12 Fe1 59.28(15) . . . . ?
C10 Fe1 C12 C13 81.58(14) . . . . ?
C15 Fe1 C12 C13 -145.61(14) . . . . ?
C11 Fe1 C12 C13 119.57(19) . . . . ?
C19 Fe1 C12 C13 176.64(14) . . . . ?
C16 Fe1 C12 C13 -101.61(15) . . . . ?
C14 Fe1 C12 C13 37.30(13) . . . . ?
C17 Fe1 C12 C13 -64.1(2) . . . . ?
C18 Fe1 C12 C13 151(6) . . . . ?
C10 Fe1 C12 C11 -37.99(13) . . . . ?
C15 Fe1 C12 C11 94.83(15) . . . . ?
C19 Fe1 C12 C11 57.1(2) . . . . ?
C16 Fe1 C12 C11 138.82(15) . . . . ?
C14 Fe1 C12 C11 -82.27(14) . . . . ?
C17 Fe1 C12 C11 176.32(15) . . . . ?
C18 Fe1 C12 C11 31(6) . . . . ?
C13 Fe1 C12 C11 -119.57(19) . . . . ?
C11 C12 C13 C14 -0.2(2) . . . . ?
Fe1 C12 C13 C14 -58.89(15) . . . . ?
C11 C12 C13 Fe1 58.73(15) . . . . ?
C10 Fe1 C13 C12 -81.89(14) . . . . ?
C15 Fe1 C13 C12 56.9(2) . . . . ?
C11 Fe1 C13 C12 -37.58(13) . . . . ?
C19 Fe1 C13 C12 -80(3) . . . . ?
C16 Fe1 C13 C12 96.56(15) . . . . ?
C14 Fe1 C13 C12 -119.81(19) . . . . ?
C17 Fe1 C13 C12 141.23(14) . . . . ?
C18 Fe1 C13 C12 -179.31(14) . . . . ?
C10 Fe1 C13 C14 37.91(13) . . . . ?
C15 Fe1 C13 C14 176.66(15) . . . . ?
C11 Fe1 C13 C14 82.23(14) . . . . ?
C19 Fe1 C13 C14 40(3) . . . . ?
C16 Fe1 C13 C14 -143.64(14) . . . . ?
C17 Fe1 C13 C14 -98.97(15) . . . . ?
C18 Fe1 C13 C14 -59.50(19) . . . . ?
C12 Fe1 C13 C14 119.81(19) . . . . ?
C12 C13 C14 C10 0.3(2) . . . . ?
Fe1 C13 C14 C10 -58.86(15) . . . . ?
C12 C13 C14 Fe1 59.13(15) . . . . ?
C11 C10 C14 C13 -0.3(2) . . . . ?
C9 C10 C14 C13 -178.18(19) . . . . ?
Fe1 C10 C14 C13 59.58(15) . . . . ?
C11 C10 C14 Fe1 -59.86(14) . . . . ?
C9 C10 C14 Fe1 122.2(2) . . . . ?
C10 Fe1 C14 C13 -119.39(19) . . . . ?
C15 Fe1 C14 C13 -129(2) . . . . ?
C11 Fe1 C14 C13 -80.99(14) . . . . ?
C19 Fe1 C14 C13 -177.86(14) . . . . ?
C16 Fe1 C14 C13 61.5(2) . . . . ?
C17 Fe1 C14 C13 99.97(15) . . . . ?
C18 Fe1 C14 C13 143.74(14) . . . . ?
C12 Fe1 C14 C13 -37.15(13) . . . . ?
C15 Fe1 C14 C10 -10(2) . . . . ?
C11 Fe1 C14 C10 38.40(13) . . . . ?
C19 Fe1 C14 C10 -58.47(19) . . . . ?
C16 Fe1 C14 C10 -179.07(15) . . . . ?
C17 Fe1 C14 C10 -140.64(14) . . . . ?
C18 Fe1 C14 C10 -96.87(14) . . . . ?
C12 Fe1 C14 C10 82.23(14) . . . . ?
C13 Fe1 C14 C10 119.39(19) . . . . ?
C10 Fe1 C15 C19 -60.34(19) . . . . ?
C11 Fe1 C15 C19 -98.48(15) . . . . ?
C16 Fe1 C15 C19 118.8(2) . . . . ?
C14 Fe1 C15 C19 -51(2) . . . . ?
C17 Fe1 C15 C19 80.67(16) . . . . ?
C18 Fe1 C15 C19 37.16(14) . . . . ?
C12 Fe1 C15 C19 -141.97(14) . . . . ?
C13 Fe1 C15 C19 -177.64(15) . . . . ?
C10 Fe1 C15 C16 -179.17(14) . . . . ?
C11 Fe1 C15 C16 142.69(14) . . . . ?
C19 Fe1 C15 C16 -118.8(2) . . . . ?
C14 Fe1 C15 C16 -170(2) . . . . ?
C17 Fe1 C15 C16 -38.16(15) . . . . ?
C18 Fe1 C15 C16 -81.68(16) . . . . ?
C12 Fe1 C15 C16 99.20(15) . . . . ?
C13 Fe1 C15 C16 63.5(2) . . . . ?
C19 C15 C16 C17 -0.2(3) . . . . ?
Fe1 C15 C16 C17 59.84(16) . . . . ?
C19 C15 C16 Fe1 -60.00(16) . . . . ?
C10 Fe1 C16 C15 10.5(19) . . . . ?
C11 Fe1 C16 C15 -58.4(2) . . . . ?
C19 Fe1 C16 C15 37.74(14) . . . . ?
C14 Fe1 C16 C15 179.23(15) . . . . ?
C17 Fe1 C16 C15 118.3(2) . . . . ?
C18 Fe1 C16 C15 80.89(15) . . . . ?
C12 Fe1 C16 C15 -98.18(15) . . . . ?
C13 Fe1 C16 C15 -142.11(14) . . . . ?
C10 Fe1 C16 C17 -107.8(18) . . . . ?
C15 Fe1 C16 C17 -118.3(2) . . . . ?
C11 Fe1 C16 C17 -176.73(14) . . . . ?
C19 Fe1 C16 C17 -80.55(16) . . . . ?
C14 Fe1 C16 C17 61.0(2) . . . . ?
C18 Fe1 C16 C17 -37.40(15) . . . . ?
C12 Fe1 C16 C17 143.53(14) . . . . ?
C13 Fe1 C16 C17 99.61(16) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
Fe1 C16 C17 C18 59.67(16) . . . . ?
C15 C16 C17 Fe1 -59.59(16) . . . . ?
C10 Fe1 C17 C18 56.1(2) . . . . ?
C15 Fe1 C17 C18 -80.99(15) . . . . ?
C11 Fe1 C17 C18 -64(2) . . . . ?
C19 Fe1 C17 C18 -37.20(14) . . . . ?
C16 Fe1 C17 C18 -119.2(2) . . . . ?
C14 Fe1 C17 C18 96.81(15) . . . . ?
C12 Fe1 C17 C18 -179.20(14) . . . . ?
C13 Fe1 C17 C18 141.22(14) . . . . ?
C10 Fe1 C17 C16 175.31(14) . . . . ?
C15 Fe1 C17 C16 38.20(15) . . . . ?
C11 Fe1 C17 C16 56(2) . . . . ?
C19 Fe1 C17 C16 82.00(16) . . . . ?
C14 Fe1 C17 C16 -144.00(15) . . . . ?
C18 Fe1 C17 C16 119.2(2) . . . . ?
C12 Fe1 C17 C16 -60.0(2) . . . . ?
C13 Fe1 C17 C16 -99.58(16) . . . . ?
C16 C17 C18 C19 0.0(3) . . . . ?
Fe1 C17 C18 C19 59.50(16) . . . . ?
C16 C17 C18 Fe1 -59.48(16) . . . . ?
C10 Fe1 C18 C19 95.19(15) . . . . ?
C15 Fe1 C18 C19 -37.62(15) . . . . ?
C11 Fe1 C18 C19 57.0(2) . . . . ?
C16 Fe1 C18 C19 -81.64(16) . . . . ?
C14 Fe1 C18 C19 139.47(14) . . . . ?
C17 Fe1 C18 C19 -119.4(2) . . . . ?
C12 Fe1 C18 C19 26(6) . . . . ?
C13 Fe1 C18 C19 176.57(15) . . . . ?
C10 Fe1 C18 C17 -145.40(14) . . . . ?
C15 Fe1 C18 C17 81.78(16) . . . . ?
C11 Fe1 C18 C17 176.40(15) . . . . ?
C19 Fe1 C18 C17 119.4(2) . . . . ?
C16 Fe1 C18 C17 37.77(16) . . . . ?
C14 Fe1 C18 C17 -101.13(15) . . . . ?
C12 Fe1 C18 C17 146(6) . . . . ?
C13 Fe1 C18 C17 -64.0(2) . . . . ?
C17 C18 C19 C15 -0.1(3) . . . . ?
Fe1 C18 C19 C15 59.40(16) . . . . ?
C17 C18 C19 Fe1 -59.51(16) . . . . ?
C16 C15 C19 C18 0.2(3) . . . . ?
Fe1 C15 C19 C18 -59.83(16) . . . . ?
C16 C15 C19 Fe1 60.00(16) . . . . ?
C10 Fe1 C19 C18 -100.09(15) . . . . ?
C15 Fe1 C19 C18 119.4(2) . . . . ?
C11 Fe1 C19 C18 -143.80(14) . . . . ?
C16 Fe1 C19 C18 81.43(16) . . . . ?
C14 Fe1 C19 C18 -63.75(19) . . . . ?
C17 Fe1 C19 C18 37.45(15) . . . . ?
C12 Fe1 C19 C18 -179.39(14) . . . . ?
C13 Fe1 C19 C18 -102(2) . . . . ?
C10 Fe1 C19 C15 140.54(14) . . . . ?
C11 Fe1 C19 C15 96.83(15) . . . . ?
C16 Fe1 C19 C15 -37.94(15) . . . . ?
C14 Fe1 C19 C15 176.87(14) . . . . ?
C17 Fe1 C19 C15 -81.92(16) . . . . ?
C18 Fe1 C19 C15 -119.4(2) . . . . ?
C12 Fe1 C19 C15 61.2(2) . . . . ?
C13 Fe1 C19 C15 138(2) . . . . ?

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
C2 H2 Br2 0.95 2.87 3.609(2) 136.0 4_586
C4 H4 Br1 0.95 2.91 3.815(2) 158.5 4_576

_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_theta_full        66.50
_diffrn_measured_fraction_theta_full 0.964
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.070
####################################################################### 
# 
# 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_obuah07
_database_code_depnum_ccdc_archive 'CCDC 1062601'
_audit_update_record             
;
2015-04-30 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;
_audit_creation_date             2015-04-30
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.11.03 svn.r3071 for OlexSys, GUI svn.r4932)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H19 Br2 Fe N3 Ni'
_chemical_formula_sum            'C20 H19 Br2 Fe N3 Ni'
_chemical_formula_weight         575.76
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
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'
Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   14.2482(3)
_cell_length_b                   9.8031(2)
_cell_length_c                   14.1378(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.7930(10)
_cell_angle_gamma                90
_cell_volume                     1960.86(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   0.250
_shelx_estimated_absorpt_T_min   0.082
_exptl_absorpt_coefficient_mu    11.972
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.950
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.923
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12245
_diffrn_reflns_point_group_measured_fraction_full 0.923
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        66.290
_diffrn_reflns_theta_max         66.290
_diffrn_reflns_theta_min         5.490
_diffrn_ambient_temperature      100.03
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.923
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3110
_reflns_number_total             3182
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         1.284
_refine_diff_density_min         -0.665
_refine_diff_density_rms         0.166
_refine_ls_extinction_coef       0.0002(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0502
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0933P)²+1.5892P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1290
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C15(H15), C14(H14),
 C13(H13), C12(H12), C9(H9), C4(H4), C3(H3), C2(H2), C1(H1)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br2 Br 0.23388(3) 0.13084(4) 0.18240(3) 0.0307(2) Uani 1 1 d . . . . .
Br1 Br 0.47143(3) -0.06912(4) 0.18212(3) 0.0326(2) Uani 1 1 d . . . . .
Ni1 Ni 0.32446(5) -0.05748(6) 0.24503(5) 0.0265(2) Uani 1 1 d . . . . .
Fe1 Fe 0.04955(4) -0.25421(6) 0.08452(5) 0.0270(2) Uani 1 1 d . . . . .
N3 N 0.2959(2) -0.2552(3) 0.2608(3) 0.0270(7) Uani 1 1 d . . . . .
N2 N 0.3325(2) -0.3169(3) 0.3442(2) 0.0271(7) Uani 1 1 d . . . . .
N1 N 0.3518(2) -0.0241(3) 0.3862(3) 0.0271(7) Uani 1 1 d . . . . .
C16 C -0.0011(3) -0.1969(5) 0.2083(4) 0.0397(10) Uani 1 1 d . . . . .
H16 H 0.0325 -0.1997 0.2705 0.048 Uiso 1 1 calc R . . . .
C17 C -0.0041(3) -0.0836(5) 0.1431(3) 0.0337(9) Uani 1 1 d . . . . .
H17 H 0.0275 0.0012 0.1544 0.040 Uiso 1 1 calc R . . . .
C18 C -0.0624(3) -0.1217(4) 0.0592(3) 0.0326(9) Uani 1 1 d . . . . .
H18 H -0.0770 -0.0664 0.0043 0.039 Uiso 1 1 calc R . . . .
C19 C -0.0956(3) -0.2566(5) 0.0709(4) 0.0362(10) Uani 1 1 d . . . . .
H19 H -0.1362 -0.3070 0.0255 0.043 Uiso 1 1 calc R . . . .
C20 C -0.0568(3) -0.3030(5) 0.1636(3) 0.0378(10) Uani 1 1 d . . . . .
H20 H -0.0669 -0.3900 0.1902 0.045 Uiso 1 1 calc R . . . .
C15 C 0.1841(3) -0.2075(4) 0.0603(3) 0.0282(8) Uani 1 1 d . . . . .
H15 H 0.2157 -0.1235 0.0754 0.034 Uiso 1 1 calc R . . . .
C14 C 0.1290(3) -0.2399(4) -0.0278(3) 0.0311(9) Uani 1 1 d . . . . .
H14 H 0.1175 -0.1815 -0.0815 0.037 Uiso 1 1 calc R . . . .
C13 C 0.0944(3) -0.3748(4) -0.0210(3) 0.0325(9) Uani 1 1 d . . . . .
H13 H 0.0556 -0.4222 -0.0695 0.039 Uiso 1 1 calc R . . . .
C12 C 0.1275(3) -0.4268(4) 0.0705(3) 0.0310(9) Uani 1 1 d . . . . .
H12 H 0.1146 -0.5150 0.0937 0.037 Uiso 1 1 calc R . . . .
C11 C 0.1835(3) -0.3236(4) 0.1221(3) 0.0277(8) Uani 1 1 d . . . . .
C10 C 0.2335(3) -0.3443(4) 0.2176(3) 0.0272(8) Uani 1 1 d . . . . .
C9 C 0.2295(3) -0.4615(4) 0.2733(3) 0.0292(8) Uani 1 1 d . . . . .
H9 H 0.1907 -0.5394 0.2588 0.035 Uiso 1 1 calc R . . . .
C8 C 0.2934(3) -0.4414(4) 0.3539(3) 0.0273(8) Uani 1 1 d . . . . .
C7 C 0.3194(3) -0.5322(4) 0.4364(3) 0.0310(9) Uani 1 1 d . . . . .
H7A H 0.3733 -0.5890 0.4244 0.046 Uiso 1 1 calc GR . . . .
H7B H 0.2656 -0.5908 0.4460 0.046 Uiso 1 1 calc GR . . . .
H7C H 0.3366 -0.4770 0.4936 0.046 Uiso 1 1 calc GR . . . .
C6 C 0.4128(3) -0.2558(4) 0.4017(3) 0.0290(9) Uani 1 1 d . . . . .
H6A H 0.4638 -0.2392 0.3612 0.035 Uiso 1 1 calc R . . . .
H6B H 0.4371 -0.3204 0.4525 0.035 Uiso 1 1 calc R . . . .
C5 C 0.3875(3) -0.1223(4) 0.4467(3) 0.0274(8) Uani 1 1 d . . . . .
C4 C 0.4035(3) -0.1018(4) 0.5434(3) 0.0301(9) Uani 1 1 d . . . . .
H4 H 0.4292 -0.1729 0.5842 0.036 Uiso 1 1 calc R . . . .
C3 C 0.3818(3) 0.0231(4) 0.5810(3) 0.0302(8) Uani 1 1 d . . . . .
H3 H 0.3915 0.0386 0.6478 0.036 Uiso 1 1 calc R . . . .
C2 C 0.3455(3) 0.1255(4) 0.5187(3) 0.0326(9) Uani 1 1 d . . . . .
H2 H 0.3312 0.2131 0.5420 0.039 Uiso 1 1 calc R . . . .
C1 C 0.3310(3) 0.0973(4) 0.4233(3) 0.0300(8) Uani 1 1 d . . . . .
H1 H 0.3049 0.1666 0.3811 0.036 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br2 Ni1 2.3637(8) . ?
Br1 Ni1 2.3728(8) . ?
Ni1 N3 1.999(3) . ?
Ni1 N1 2.015(4) . ?
Fe1 C16 2.049(5) . ?
Fe1 C17 2.053(4) . ?
Fe1 C18 2.055(4) . ?
Fe1 C19 2.054(5) . ?
Fe1 C20 2.043(4) . ?
Fe1 C15 2.039(4) . ?
Fe1 C14 2.061(4) . ?
Fe1 C13 2.063(5) . ?
Fe1 C12 2.046(4) . ?
Fe1 C11 2.037(4) . ?
N3 N2 1.372(5) . ?
N3 C10 1.341(5) . ?
N2 C8 1.356(5) . ?
N2 C6 1.452(5) . ?
N1 C5 1.347(5) . ?
N1 C1 1.347(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.440(7) . ?
C16 C20 1.412(8) . ?
C17 H17 0.9500 . ?
C17 C18 1.416(7) . ?
C18 H18 0.9500 . ?
C18 C19 1.420(6) . ?
C19 H19 0.9500 . ?
C19 C20 1.434(7) . ?
C20 H20 0.9500 . ?
C15 H15 0.9500 . ?
C15 C14 1.427(6) . ?
C15 C11 1.436(6) . ?
C14 H14 0.9500 . ?
C14 C13 1.418(6) . ?
C13 H13 0.9500 . ?
C13 C12 1.418(7) . ?
C12 H12 0.9500 . ?
C12 C11 1.434(6) . ?
C11 C10 1.464(6) . ?
C10 C9 1.398(6) . ?
C9 H9 0.9500 . ?
C9 C8 1.385(6) . ?
C8 C7 1.479(6) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C5 1.516(6) . ?
C5 C4 1.374(7) . ?
C4 H4 0.9500 . ?
C4 C3 1.384(7) . ?
C3 H3 0.9500 . ?
C3 C2 1.394(6) . ?
C2 H2 0.9500 . ?
C2 C1 1.370(7) . ?
C1 H1 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
Br2 Ni1 Br1 111.35(3) . . ?
N3 Ni1 Br2 133.62(10) . . ?
N3 Ni1 Br1 101.29(10) . . ?
N3 Ni1 N1 93.72(14) . . ?
N1 Ni1 Br2 106.09(10) . . ?
N1 Ni1 Br1 107.68(10) . . ?
C16 Fe1 C17 41.12(19) . . ?
C16 Fe1 C18 68.33(19) . . ?
C16 Fe1 C19 68.3(2) . . ?
C16 Fe1 C14 157.0(2) . . ?
C16 Fe1 C13 160.9(2) . . ?
C17 Fe1 C18 40.31(18) . . ?
C17 Fe1 C19 68.20(18) . . ?
C17 Fe1 C14 121.33(18) . . ?
C17 Fe1 C13 156.96(19) . . ?
C18 Fe1 C14 107.99(18) . . ?
C18 Fe1 C13 122.46(18) . . ?
C19 Fe1 C18 40.43(18) . . ?
C19 Fe1 C14 124.6(2) . . ?
C19 Fe1 C13 108.67(18) . . ?
C20 Fe1 C16 40.4(2) . . ?
C20 Fe1 C17 68.57(19) . . ?
C20 Fe1 C18 68.44(19) . . ?
C20 Fe1 C19 41.0(2) . . ?
C20 Fe1 C14 161.4(2) . . ?
C20 Fe1 C13 125.06(19) . . ?
C20 Fe1 C12 107.77(18) . . ?
C15 Fe1 C16 120.99(19) . . ?
C15 Fe1 C17 106.66(17) . . ?
C15 Fe1 C18 123.69(18) . . ?
C15 Fe1 C19 160.55(19) . . ?
C15 Fe1 C20 156.52(19) . . ?
C15 Fe1 C14 40.75(18) . . ?
C15 Fe1 C13 68.27(17) . . ?
C15 Fe1 C12 68.77(17) . . ?
C14 Fe1 C13 40.24(18) . . ?
C12 Fe1 C16 124.00(19) . . ?
C12 Fe1 C17 160.82(18) . . ?
C12 Fe1 C18 157.60(18) . . ?
C12 Fe1 C19 122.22(18) . . ?
C12 Fe1 C14 68.16(18) . . ?
C12 Fe1 C13 40.38(18) . . ?
C11 Fe1 C16 106.42(18) . . ?
C11 Fe1 C17 123.27(17) . . ?
C11 Fe1 C18 160.15(17) . . ?
C11 Fe1 C19 157.31(18) . . ?
C11 Fe1 C20 120.79(18) . . ?
C11 Fe1 C15 41.24(17) . . ?
C11 Fe1 C14 68.92(17) . . ?
C11 Fe1 C13 68.68(17) . . ?
C11 Fe1 C12 41.11(16) . . ?
N2 N3 Ni1 117.5(3) . . ?
C10 N3 Ni1 135.6(3) . . ?
C10 N3 N2 105.6(3) . . ?
N3 N2 C6 119.5(3) . . ?
C8 N2 N3 111.4(3) . . ?
C8 N2 C6 128.4(3) . . ?
C5 N1 Ni1 121.8(3) . . ?
C1 N1 Ni1 120.2(3) . . ?
C1 N1 C5 118.0(4) . . ?
Fe1 C16 H16 126.3 . . ?
C17 C16 Fe1 69.6(3) . . ?
C17 C16 H16 126.0 . . ?
C20 C16 Fe1 69.6(3) . . ?
C20 C16 H16 126.0 . . ?
C20 C16 C17 108.0(4) . . ?
Fe1 C17 H17 126.2 . . ?
C16 C17 Fe1 69.3(3) . . ?
C16 C17 H17 126.2 . . ?
C18 C17 Fe1 69.9(2) . . ?
C18 C17 C16 107.6(4) . . ?
C18 C17 H17 126.2 . . ?
Fe1 C18 H18 126.4 . . ?
C17 C18 Fe1 69.8(2) . . ?
C17 C18 H18 125.7 . . ?
C17 C18 C19 108.6(4) . . ?
C19 C18 Fe1 69.7(2) . . ?
C19 C18 H18 125.7 . . ?
Fe1 C19 H19 126.5 . . ?
C18 C19 Fe1 69.8(2) . . ?
C18 C19 H19 126.2 . . ?
C18 C19 C20 107.7(4) . . ?
C20 C19 Fe1 69.1(3) . . ?
C20 C19 H19 126.2 . . ?
Fe1 C20 H20 125.7 . . ?
C16 C20 Fe1 70.0(3) . . ?
C16 C20 C19 108.1(4) . . ?
C16 C20 H20 125.9 . . ?
C19 C20 Fe1 69.9(2) . . ?
C19 C20 H20 125.9 . . ?
Fe1 C15 H15 125.9 . . ?
C14 C15 Fe1 70.4(2) . . ?
C14 C15 H15 125.9 . . ?
C14 C15 C11 108.2(4) . . ?
C11 C15 Fe1 69.3(2) . . ?
C11 C15 H15 125.9 . . ?
Fe1 C14 H14 126.8 . . ?
C15 C14 Fe1 68.8(2) . . ?
C15 C14 H14 126.0 . . ?
C13 C14 Fe1 70.0(3) . . ?
C13 C14 C15 108.0(4) . . ?
C13 C14 H14 126.0 . . ?
Fe1 C13 H13 126.8 . . ?
C14 C13 Fe1 69.8(2) . . ?
C14 C13 H13 125.8 . . ?
C12 C13 Fe1 69.2(2) . . ?
C12 C13 C14 108.4(4) . . ?
C12 C13 H13 125.8 . . ?
Fe1 C12 H12 126.2 . . ?
C13 C12 Fe1 70.4(2) . . ?
C13 C12 H12 125.8 . . ?
C13 C12 C11 108.4(4) . . ?
C11 C12 Fe1 69.1(2) . . ?
C11 C12 H12 125.8 . . ?
C15 C11 Fe1 69.5(2) . . ?
C15 C11 C10 129.3(4) . . ?
C12 C11 Fe1 69.8(2) . . ?
C12 C11 C15 107.0(4) . . ?
C12 C11 C10 123.5(4) . . ?
C10 C11 Fe1 128.7(3) . . ?
N3 C10 C11 123.6(4) . . ?
N3 C10 C9 110.4(4) . . ?
C9 C10 C11 125.9(4) . . ?
C10 C9 H9 126.9 . . ?
C8 C9 C10 106.3(4) . . ?
C8 C9 H9 126.9 . . ?
N2 C8 C9 106.4(4) . . ?
N2 C8 C7 123.6(4) . . ?
C9 C8 C7 130.0(4) . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C6 H6A 109.1 . . ?
N2 C6 H6B 109.1 . . ?
N2 C6 C5 112.4(3) . . ?
H6A C6 H6B 107.9 . . ?
C5 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
N1 C5 C6 116.2(4) . . ?
N1 C5 C4 122.1(4) . . ?
C4 C5 C6 121.6(4) . . ?
C5 C4 H4 120.2 . . ?
C5 C4 C3 119.6(4) . . ?
C3 C4 H4 120.2 . . ?
C4 C3 H3 120.8 . . ?
C4 C3 C2 118.5(4) . . ?
C2 C3 H3 120.8 . . ?
C3 C2 H2 120.7 . . ?
C1 C2 C3 118.6(4) . . ?
C1 C2 H2 120.7 . . ?
N1 C1 C2 123.2(4) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ni1 N3 N2 C8 168.0(3) . . . . ?
Ni1 N3 N2 C6 -20.5(4) . . . . ?
Ni1 N3 C10 C11 19.6(6) . . . . ?
Ni1 N3 C10 C9 -165.0(3) . . . . ?
Ni1 N1 C5 C6 4.4(5) . . . . ?
Ni1 N1 C5 C4 -177.8(3) . . . . ?
Ni1 N1 C1 C2 178.4(3) . . . . ?
Fe1 C16 C17 C18 59.7(3) . . . . ?
Fe1 C16 C20 C19 -59.8(3) . . . . ?
Fe1 C17 C18 C19 59.1(3) . . . . ?
Fe1 C18 C19 C20 58.9(3) . . . . ?
Fe1 C19 C20 C16 59.8(3) . . . . ?
Fe1 C15 C14 C13 -59.2(3) . . . . ?
Fe1 C15 C11 C12 59.9(3) . . . . ?
Fe1 C15 C11 C10 -123.8(4) . . . . ?
Fe1 C14 C13 C12 -58.5(3) . . . . ?
Fe1 C13 C12 C11 -58.9(3) . . . . ?
Fe1 C12 C11 C15 -59.7(3) . . . . ?
Fe1 C12 C11 C10 123.7(4) . . . . ?
Fe1 C11 C10 N3 -99.3(4) . . . . ?
Fe1 C11 C10 C9 86.0(5) . . . . ?
N3 N2 C8 C9 0.5(4) . . . . ?
N3 N2 C8 C7 179.6(4) . . . . ?
N3 N2 C6 C5 68.7(5) . . . . ?
N3 C10 C9 C8 -0.3(5) . . . . ?
N2 N3 C10 C11 -174.8(3) . . . . ?
N2 N3 C10 C9 0.6(4) . . . . ?
N2 C6 C5 N1 -57.8(5) . . . . ?
N2 C6 C5 C4 124.3(4) . . . . ?
N1 C5 C4 C3 0.4(6) . . . . ?
C16 C17 C18 Fe1 -59.3(3) . . . . ?
C16 C17 C18 C19 -0.2(5) . . . . ?
C17 C16 C20 Fe1 59.2(3) . . . . ?
C17 C16 C20 C19 -0.6(5) . . . . ?
C17 C18 C19 Fe1 -59.1(3) . . . . ?
C17 C18 C19 C20 -0.2(5) . . . . ?
C18 C19 C20 Fe1 -59.4(3) . . . . ?
C18 C19 C20 C16 0.5(5) . . . . ?
C20 C16 C17 Fe1 -59.2(3) . . . . ?
C20 C16 C17 C18 0.4(5) . . . . ?
C15 C14 C13 Fe1 58.5(3) . . . . ?
C15 C14 C13 C12 0.0(5) . . . . ?
C15 C11 C10 N3 -4.9(6) . . . . ?
C15 C11 C10 C9 -179.7(4) . . . . ?
C14 C15 C11 Fe1 -59.9(3) . . . . ?
C14 C15 C11 C12 0.0(5) . . . . ?
C14 C15 C11 C10 176.2(4) . . . . ?
C14 C13 C12 Fe1 58.9(3) . . . . ?
C14 C13 C12 C11 0.0(5) . . . . ?
C13 C12 C11 Fe1 59.7(3) . . . . ?
C13 C12 C11 C15 0.0(5) . . . . ?
C13 C12 C11 C10 -176.5(4) . . . . ?
C12 C11 C10 N3 170.7(4) . . . . ?
C12 C11 C10 C9 -4.0(6) . . . . ?
C11 C15 C14 Fe1 59.2(3) . . . . ?
C11 C15 C14 C13 0.0(5) . . . . ?
C11 C10 C9 C8 175.0(4) . . . . ?
C10 N3 N2 C8 -0.7(4) . . . . ?
C10 N3 N2 C6 170.9(3) . . . . ?
C10 C9 C8 N2 -0.1(4) . . . . ?
C10 C9 C8 C7 -179.1(4) . . . . ?
C8 N2 C6 C5 -121.4(4) . . . . ?
C6 N2 C8 C9 -170.1(4) . . . . ?
C6 N2 C8 C7 9.0(6) . . . . ?
C6 C5 C4 C3 178.1(4) . . . . ?
C5 N1 C1 C2 0.8(6) . . . . ?
C5 C4 C3 C2 -1.0(6) . . . . ?
C4 C3 C2 C1 1.4(6) . . . . ?
C3 C2 C1 N1 -1.4(7) . . . . ?
C1 N1 C5 C6 -178.2(4) . . . . ?
C1 N1 C5 C4 -0.3(6) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
