# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_1_150K
_database_code_depnum_ccdc_archive 'CCDC 1414293'
_audit_update_record             
;
2015-10-25 deposited with the CCDC.
2015-10-28 downloaded from the CCDC.
;
#*************************************************************************

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H24 B2 Fe N6'
_chemical_formula_sum            'C16 H24 B2 Fe N6'
_chemical_formula_weight         377.88

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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           41
_space_group_name_H-M_alt        'A b a 2'
_space_group_name_Hall           'A 2 -2ac'

_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'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z+1/2'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z+1'
'x+1/2, -y+1/2, z+1'

_cell_length_a                   14.3553(8)
_cell_length_b                   15.2389(11)
_cell_length_c                   8.8543(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1937.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2286
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      25.13

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.789
_shelx_estimated_absorpt_T_min   0.852
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6695
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2013)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6315
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.016
_diffrn_reflns_theta_max         25.243
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             1510
_reflns_number_gt                1283
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.874
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.994

_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       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       APEX2
_computing_data_reduction        APEX2
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    
;
OLEX2 (Dolomanov et al., 2009) and DIAMOND (Brandenburg & Putz, 2005)'
;
_computing_publication_material  OLEX2

_refine_special_details          
;
1. Refined as a 2-component inversion twin.
 Scales: 0.96(4) 0.04(4)
2. Fixed Uiso
 At 1.5 times of:
  B(H,H,H) group
 At 1.2 times of:
  All C(H) groups, all C(H,H) groups, N(H) group
3.a Riding coordinates:
 B1(H1A,H1B,H1C)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C6(H6A,H6B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C2(H2A), C3(H3)
4. H2 attached to N2 was located in a difference Fourier map,
 and the N-H distance was restrainted to 0.86(2) ANG.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0290P)²+0.6335P] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.04(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1510
_refine_ls_number_parameters     118
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_ref         0.0630
_refine_ls_wR_factor_gt          0.0591
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
Fe1 Fe 0.5000 0.0000 0.73891(12) 0.01861(17) Uani 1 2 d S T P . .
N3 N 0.4689(3) 0.0868(3) 0.5871(4) 0.0226(9) Uani 1 1 d . . . . .
N2 N 0.4646(3) 0.0833(3) 0.9050(4) 0.0260(9) Uani 1 1 d D . . . .
H2 H 0.490(3) 0.1322(18) 0.899(5) 0.031 Uiso 1 1 d D U . . .
N1 N 0.36868(17) -0.03777(17) 0.7566(5) 0.0219(6) Uani 1 1 d . . . . .
C8 C 0.4507(3) 0.1399(2) 0.5001(5) 0.0230(8) Uani 1 1 d . . . . .
C1 C 0.3303(2) -0.1110(2) 0.6993(4) 0.0303(11) Uani 1 1 d . . . . .
H1 H 0.3681 -0.1485 0.6393 0.036 Uiso 1 1 calc R U . . .
C7 C 0.5025(3) 0.0489(2) 1.0483(5) 0.0319(9) Uani 1 1 d . . . . .
H7A H 0.4663 0.0726 1.1343 0.038 Uiso 1 1 calc R U . . .
H7B H 0.5681 0.0679 1.0601 0.038 Uiso 1 1 calc R U . . .
C5 C 0.3145(3) 0.0145(3) 0.8437(4) 0.0303(10) Uani 1 1 d . . . . .
C6 C 0.3621(3) 0.0955(3) 0.9026(5) 0.0368(11) Uani 1 1 d . . . . .
H6A H 0.3462 0.1461 0.8375 0.044 Uiso 1 1 calc R U . . .
H6B H 0.3396 0.1083 1.0060 0.044 Uiso 1 1 calc R U . . .
C4 C 0.2232(3) -0.0056(3) 0.8748(5) 0.0403(11) Uani 1 1 d . . . . .
H4 H 0.1871 0.0317 0.9379 0.048 Uiso 1 1 calc R U . . .
C2 C 0.2384(2) -0.1343(3) 0.7237(6) 0.0399(11) Uani 1 1 d . . . . .
H2A H 0.2132 -0.1860 0.6798 0.048 Uiso 1 1 calc R U . . .
C3 C 0.1842(3) -0.0804(3) 0.8138(5) 0.0459(12) Uani 1 1 d . . . . .
H3 H 0.1210 -0.0947 0.8333 0.055 Uiso 1 1 calc R U . . .
B1 B 0.4244(4) 0.2130(3) 0.3807(6) 0.0339(11) Uani 1 1 d . . . . .
H1A H 0.3765 0.1903 0.3123 0.051 Uiso 1 1 d R U . . .
H1B H 0.4006 0.2648 0.4334 0.051 Uiso 1 1 d R U . . .
H1C H 0.4799 0.2290 0.3225 0.051 Uiso 1 1 d 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
Fe1 N3 1.938(4) . ?
Fe1 N3 1.938(4) 2_655 ?
Fe1 N1 1.977(2) . ?
Fe1 N1 1.977(2) 2_655 ?
Fe1 N2 2.009(4) . ?
Fe1 N2 2.009(4) 2_655 ?
N3 C8 1.147(5) . ?
N2 C7 1.477(6) . ?
N2 C6 1.484(6) . ?
N2 H2 0.83(2) . ?
N1 C1 1.344(4) . ?
N1 C5 1.354(5) . ?
C8 B1 1.581(6) . ?
C1 C2 1.383(5) . ?
C1 H1 0.9500 . ?
C7 C7 1.494(7) 2_655 ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C5 C4 1.374(6) . ?
C5 C6 1.504(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C4 C3 1.379(6) . ?
C4 H4 0.9500 . ?
C2 C3 1.384(7) . ?
C2 H2A 0.9500 . ?
C3 H3 0.9500 . ?
B1 H1A 0.9799 . ?
B1 H1B 0.9800 . ?
B1 H1C 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
N3 Fe1 N3 92.2(2) . 2_655 ?
N3 Fe1 N1 91.95(15) . . ?
N3 Fe1 N1 94.36(15) 2_655 . ?
N3 Fe1 N1 94.36(15) . 2_655 ?
N3 Fe1 N1 91.95(15) 2_655 2_655 ?
N1 Fe1 N1 170.9(2) . 2_655 ?
N3 Fe1 N2 91.03(11) . . ?
N3 Fe1 N2 176.1(2) 2_655 . ?
N1 Fe1 N2 83.38(16) . . ?
N1 Fe1 N2 89.94(16) 2_655 . ?
N3 Fe1 N2 176.1(2) . 2_655 ?
N3 Fe1 N2 91.03(11) 2_655 2_655 ?
N1 Fe1 N2 89.94(16) . 2_655 ?
N1 Fe1 N2 83.38(16) 2_655 2_655 ?
N2 Fe1 N2 85.8(2) . 2_655 ?
C8 N3 Fe1 178.2(4) . . ?
C7 N2 C6 115.0(4) . . ?
C7 N2 Fe1 108.2(3) . . ?
C6 N2 Fe1 108.6(3) . . ?
C7 N2 H2 102(3) . . ?
C6 N2 H2 109(3) . . ?
Fe1 N2 H2 114(3) . . ?
C1 N1 C5 117.9(3) . . ?
C1 N1 Fe1 127.0(3) . . ?
C5 N1 Fe1 115.0(3) . . ?
N3 C8 B1 179.4(4) . . ?
N1 C1 C2 123.0(4) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
N2 C7 C7 109.7(3) . 2_655 ?
N2 C7 H7A 109.7 . . ?
C7 C7 H7A 109.7 2_655 . ?
N2 C7 H7B 109.7 . . ?
C7 C7 H7B 109.7 2_655 . ?
H7A C7 H7B 108.2 . . ?
N1 C5 C4 122.1(4) . . ?
N1 C5 C6 114.8(3) . . ?
C4 C5 C6 123.2(4) . . ?
N2 C6 C5 110.7(3) . . ?
N2 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C5 C4 C3 119.5(4) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C1 C2 C3 118.3(4) . . ?
C1 C2 H2A 120.9 . . ?
C3 C2 H2A 120.9 . . ?
C4 C3 C2 119.2(4) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C8 B1 H1A 109.4 . . ?
C8 B1 H1B 109.5 . . ?
H1A B1 H1B 109.5 . . ?
C8 B1 H1C 109.5 . . ?
H1A B1 H1C 109.5 . . ?
H1B B1 H1C 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
C5 N1 C1 C2 0.9(6) . . . . ?
Fe1 N1 C1 C2 176.7(3) . . . . ?
C6 N2 C7 C7 85.6(5) . . . 2_655 ?
Fe1 N2 C7 C7 -36.0(5) . . . 2_655 ?
C1 N1 C5 C4 0.4(6) . . . . ?
Fe1 N1 C5 C4 -176.0(3) . . . . ?
C1 N1 C5 C6 -179.5(3) . . . . ?
Fe1 N1 C5 C6 4.1(4) . . . . ?
C7 N2 C6 C5 -91.7(4) . . . . ?
Fe1 N2 C6 C5 29.7(4) . . . . ?
N1 C5 C6 N2 -22.8(5) . . . . ?
C4 C5 C6 N2 157.3(4) . . . . ?
N1 C5 C4 C3 -1.2(6) . . . . ?
C6 C5 C4 C3 178.7(4) . . . . ?
N1 C1 C2 C3 -1.3(6) . . . . ?
C5 C4 C3 C2 0.8(6) . . . . ?
C1 C2 C3 C4 0.4(6) . . . . ?

_refine_diff_density_max         0.181
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.045

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_1_373K
_database_code_depnum_ccdc_archive 'CCDC 1414294'
_audit_update_record             
;
2015-10-25 deposited with the CCDC.
2015-10-28 downloaded from the CCDC.
;
#*************************************************************************
_audit_creation_method           SHELXL-2013
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H24 B2 Fe N6'
_chemical_formula_sum            'C16 H24 B2 Fe N6'
_chemical_formula_weight         377.88
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      orthorhombic
_space_group_IT_number           41
_space_group_name_H-M_alt        'A e a 2'
_space_group_name_Hall           'A 2 -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z+1/2'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z+1'
'x+1/2, -y+1/2, z+1'

_cell_length_a                   14.3196(18)
_cell_length_b                   15.4416(14)
_cell_length_c                   9.4510(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2089.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4064
_cell_measurement_temperature    373(2)
_cell_measurement_theta_max      55.05
_cell_measurement_theta_min      5.99
_shelx_estimated_absorpt_T_max   0.951
_shelx_estimated_absorpt_T_min   0.930
_exptl_absorpt_coefficient_mu    0.731
_exptl_absorpt_correction_T_max  0.7269
_exptl_absorpt_correction_T_min  0.6268
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.070
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6699
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.463
_diffrn_reflns_theta_min         2.997
_diffrn_ambient_temperature      373(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'large-area curved image plate detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.839
_reflns_Friedel_fraction_full    0.963
_reflns_Friedel_fraction_max     0.948
_reflns_number_gt                1174
_reflns_number_total             2319
_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       'Rigaku R-Axis SPIDER'
_computing_data_reduction        ?
_computing_molecular_graphics    
;
OLEX2 (Dolomanov et al., 2009) and DIAMOND (Brandenburg & Putz, 2005)'
;
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 422 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2319
_refine_ls_number_restraints     340
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0395
_refine_ls_restrained_S_all      1.035
_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)+(0.0324P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0728
_refine_ls_wR_factor_ref         0.1001
_refine_special_details          
;
1. The chelate ligand was refined with a two-fold disorder model.
 Restraints:
  C-C bond lengths within the pyridyl group: 1.38(2) ANG;
  C-N bond lengths within the pyridyl group: equal(0.02 ANG);
  The distances of C1 to C3, C2 to C4 and C3 to C5 within the pyridyl 
group: equal(0.04 ANG);
  The distances of N1 to C2 and N1 to C4 within the pyridyl 
group: equal(0.04 ANG);
  The distances of C1 to C5 within the pyridyl group of two parts: 
equal(0.04 ANG);
  The pyridyl group together with C6: lying within a plane(0.1 ANG³).
  Bond lengths of C6-C1 of two parts: 1.50(2) ANG;
  Bond lengths of N2-C6 and N2-C7: 1.48(1) ANG;
  Bond lengths of C7-C7(symmetry code: 1-x,-y,z) of two parts: 1.53(1) ANG;
  The distances of C6 to N1 of two parts: equal(0.04 ANG);
  The distances of C6 to C2 of two parts: equal(0.04 ANG);
  The distances of N2 to C1 of two parts: equal(0.04 ANG);
  The distances of C7 to C6 of two parts: equal(0.04 ANG);
  The distances of N2 to C7(symmetry code: 1-x,-y,z) of two parts: 
equal(0.04 ANG);
  The Uij components of all the atoms within the chelate ligand: 
equal(0.02 ANG²).
2. All the H atoms were positioned geometrically and refined as a riding 
model with the isotropic displacement parameters related to which they are 
bonded: Uiso(H) = 1.2 Ueq(parent) for C(H) and N(H); Uiso(H) = 1.5 Ueq
(parent) for B(H).
;
_olex2_refinement_description    
;
1. Others
 Fixed U13: Fe1(0)
 Fixed U23: Fe1(0)
 Fixed Uiso: H1A(0.21) H1B(0.21) H1C(0.21) H2A(0.135) H3A(0.126) H4A(0.109)
 H5A(0.101) H6A1(0.132) H6A2(0.132) H2A1(0.118) H7A1(0.138) H7A2(0.138)
 H2B(0.128) H3B(0.121) H4B(0.107) H5B(0.098) H6B1(0.136) H6B2(0.136)
 H2B1(0.131) H7B1(0.138) H7B2(0.138)
 Fixed X: H1A(0.6) H1B(0.6178) H1C(0.5177) Fe1(0.5) H2A(0.82) H3A(0.8901)
 H4A(0.8069) H5A(0.6528) H6A1(0.6466) H6A2(0.6801) H2A1(0.5121) H7A1(0.5959)
 H7A2(0.5592) H2B(0.8284) H3B(0.8784) H4B(0.7801) H5B(0.628) H6B1(0.677)
 H6B2(0.6717) H2B1(0.5299) H7B1(0.5345) H7B2(0.4376)
 Fixed Y: H1A(0.2658) H1B(0.1934) H1C(0.233) Fe1(0) H2A(0.0376) H3A(-0.0833)
 H4A(-0.1792) H5A(-0.147) H6A1(0.1404) H6A2(0.129) H2A1(0.1313) H7A1(-0.0246)
 H7A2(0.0521) H2B(0.0038) H3B(-0.12) H4B(-0.2023) H5B(-0.154) H6B1(0.1261)
 H6B2(0.0752) H2B1(0.1349) H7B1(0.0706) H7B2(0.0718)
 Fixed Z: H1A(0.5451) H1B(0.6581) H1C(0.6405) H2A(0.0468) H3A(0.1419)
 H4A(0.2782) H5A(0.3313) H6A1(0.1888) H6A2(0.0314) H2A1(0.0509) H7A1(-0.052)
 H7A2(-0.1472) H2B(0.082) H3B(0.1864) H4B(0.3254) H5B(0.3535) H6B1(0.1273)
 H6B2(-0.0161) H2B1(0.1109) H7B1(-0.1253) H7B2(-0.0461)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
B1 B 0.5736(8) 0.2162(5) 0.5916(10) 0.140(4) Uani 1 1 d . . . . .
H1A H 0.6000 0.2658 0.5451 0.210 Uiso 1 1 calc R U . . .
H1B H 0.6178 0.1934 0.6581 0.210 Uiso 1 1 calc R U . . .
H1C H 0.5177 0.2330 0.6405 0.210 Uiso 1 1 calc R U . . .
C8 C 0.5494(5) 0.1448(4) 0.4781(7) 0.0854(16) Uani 1 1 d . . . . .
Fe1 Fe 0.5000 0.0000 0.2509(2) 0.0703(3) Uani 1 2 d S T P . .
N3 N 0.5328(5) 0.0931(4) 0.3963(6) 0.0906(19) Uani 1 1 d . . . . .
N1A N 0.6469(16) -0.0343(15) 0.233(4) 0.082(5) Uani 0.458(18) 1 d D U P A 1
C1A C 0.6976(16) 0.0185(14) 0.149(3) 0.100(5) Uani 0.458(18) 1 d D U P A 1
C2A C 0.7878(16) 0.0012(15) 0.108(3) 0.113(6) Uani 0.458(18) 1 d D U P A 1
H2A H 0.8200 0.0376 0.0468 0.135 Uiso 0.458(18) 1 calc R U P A 1
C3A C 0.8278(16) -0.0719(15) 0.162(3) 0.105(6) Uani 0.458(18) 1 d D U P A 1
H3A H 0.8901 -0.0833 0.1419 0.126 Uiso 0.458(18) 1 calc R U P A 1
C4A C 0.7793(16) -0.1286(13) 0.245(3) 0.091(5) Uani 0.458(18) 1 d D U P A 1
H4A H 0.8069 -0.1792 0.2782 0.109 Uiso 0.458(18) 1 calc R U P A 1
C5A C 0.6875(18) -0.1083(17) 0.277(4) 0.084(5) Uani 0.458(18) 1 d D U P A 1
H5A H 0.6528 -0.1470 0.3313 0.101 Uiso 0.458(18) 1 calc R U P A 1
C6A C 0.6476(14) 0.1009(11) 0.109(2) 0.110(5) Uani 0.458(18) 1 d D U P A 1
H6A1 H 0.6466 0.1404 0.1888 0.132 Uiso 0.458(18) 1 calc R U P A 1
H6A2 H 0.6801 0.1290 0.0314 0.132 Uiso 0.458(18) 1 calc R U P A 1
N2A N 0.5502(14) 0.0794(14) 0.066(2) 0.098(5) Uani 0.458(18) 1 d D U P A 1
H2A1 H 0.5121 0.1313 0.0509 0.118 Uiso 0.458(18) 1 calc R U P A 1
C7A C 0.5484(8) 0.0199(11) -0.0606(19) 0.115(6) Uani 0.458(18) 1 d D U P A 1
H7A1 H 0.5959 -0.0246 -0.0520 0.138 Uiso 0.458(18) 1 calc R U P A 1
H7A2 H 0.5592 0.0521 -0.1472 0.138 Uiso 0.458(18) 1 calc R U P A 1
N1B N 0.6354(13) -0.0510(12) 0.232(3) 0.075(4) Uani 0.542(18) 1 d D U P A 2
C1B C 0.6943(14) -0.0038(11) 0.153(2) 0.096(4) Uani 0.542(18) 1 d D U P A 2
C2B C 0.7875(14) -0.0293(12) 0.136(2) 0.107(5) Uani 0.542(18) 1 d D U P A 2
H2B H 0.8284 0.0038 0.0820 0.128 Uiso 0.542(18) 1 calc R U P A 2
C3B C 0.8168(13) -0.1024(11) 0.199(2) 0.101(5) Uani 0.542(18) 1 d D U P A 2
H3B H 0.8784 -0.1200 0.1864 0.121 Uiso 0.542(18) 1 calc R U P A 2
C4B C 0.7594(14) -0.1519(11) 0.282(2) 0.089(5) Uani 0.542(18) 1 d D U P A 2
H4B H 0.7801 -0.2023 0.3254 0.107 Uiso 0.542(18) 1 calc R U P A 2
C5B C 0.6684(15) -0.1225(15) 0.296(3) 0.082(4) Uani 0.542(18) 1 d D U P A 2
H5B H 0.6280 -0.1540 0.3535 0.098 Uiso 0.542(18) 1 calc R U P A 2
C6B C 0.6527(13) 0.0742(11) 0.082(2) 0.113(5) Uani 0.542(18) 1 d D U P A 2
H6B1 H 0.6770 0.1261 0.1273 0.136 Uiso 0.542(18) 1 calc R U P A 2
H6B2 H 0.6717 0.0752 -0.0161 0.136 Uiso 0.542(18) 1 calc R U P A 2
N2B N 0.5488(13) 0.0752(13) 0.090(2) 0.109(5) Uani 0.542(18) 1 d D U P A 2
H2B1 H 0.5299 0.1349 0.1109 0.131 Uiso 0.542(18) 1 calc R U P A 2
C7B C 0.5007(13) 0.0490(4) -0.0436(17) 0.115(5) Uani 0.542(18) 1 d D U P A 2
H7B1 H 0.5345 0.0706 -0.1253 0.138 Uiso 0.542(18) 1 calc R U P A 2
H7B2 H 0.4376 0.0718 -0.0461 0.138 Uiso 0.542(18) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 H1A 0.9600 . ?
B1 H1B 0.9600 . ?
B1 H1C 0.9600 . ?
B1 C8 1.577(10) . ?
C8 N3 1.137(7) . ?
Fe1 N3 2.043(6) . ?
Fe1 N3 2.043(6) 2_655 ?
Fe1 N1A 2.18(2) . ?
Fe1 N1A 2.18(2) 2_655 ?
Fe1 N2A 2.25(3) 2_655 ?
Fe1 N2A 2.25(3) . ?
Fe1 N1B 2.099(17) . ?
Fe1 N1B 2.099(17) 2_655 ?
Fe1 N2B 2.03(2) . ?
Fe1 N2B 2.03(2) 2_655 ?
N1A C1A 1.348(15) . ?
N1A C5A 1.348(15) . ?
C1A C2A 1.375(18) . ?
C1A C6A 1.509(17) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.364(18) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.364(17) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.386(18) . ?
C5A H5A 0.9300 . ?
C6A H6A1 0.9700 . ?
C6A H6A2 0.9700 . ?
C6A N2A 1.491(13) . ?
N2A H2A1 0.9800 . ?
N2A C7A 1.505(13) . ?
C7A C7A 1.518(14) 2_655 ?
C7A H7A1 0.9700 . ?
C7A H7A2 0.9700 . ?
N1B C1B 1.345(14) . ?
N1B C5B 1.344(13) . ?
C1B C2B 1.401(17) . ?
C1B C6B 1.499(15) . ?
C2B H2B 0.9300 . ?
C2B C3B 1.345(16) . ?
C3B H3B 0.9300 . ?
C3B C4B 1.366(15) . ?
C4B H4B 0.9300 . ?
C4B C5B 1.387(16) . ?
C5B H5B 0.9300 . ?
C6B H6B1 0.9700 . ?
C6B H6B2 0.9700 . ?
C6B N2B 1.490(13) . ?
N2B H2B1 0.9800 . ?
N2B C7B 1.497(12) . ?
C7B C7B 1.512(13) 2_655 ?
C7B H7B1 0.9700 . ?
C7B H7B2 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A B1 H1B 109.5 . . ?
H1A B1 H1C 109.5 . . ?
H1B B1 H1C 109.5 . . ?
C8 B1 H1A 109.5 . . ?
C8 B1 H1B 109.5 . . ?
C8 B1 H1C 109.5 . . ?
N3 C8 B1 179.3(8) . . ?
N3 Fe1 N3 95.5(3) . 2_655 ?
N3 Fe1 N1A 95.9(6) . 2_655 ?
N3 Fe1 N1A 95.9(6) 2_655 . ?
N3 Fe1 N1A 90.1(9) . . ?
N3 Fe1 N1A 90.0(9) 2_655 2_655 ?
N3 Fe1 N2A 167.9(5) 2_655 . ?
N3 Fe1 N2A 93.8(4) . . ?
N3 Fe1 N2A 167.9(5) . 2_655 ?
N3 Fe1 N2A 93.8(4) 2_655 2_655 ?
N3 Fe1 N1B 96.1(8) 2_655 2_655 ?
N3 Fe1 N1B 96.1(8) . . ?
N3 Fe1 N1B 90.3(5) . 2_655 ?
N3 Fe1 N1B 90.3(5) 2_655 . ?
N1A Fe1 N1A 171.1(19) 2_655 . ?
N1A Fe1 N2A 96.6(12) 2_655 . ?
N1A Fe1 N2A 96.6(12) . 2_655 ?
N1A Fe1 N2A 76.4(8) 2_655 2_655 ?
N1A Fe1 N2A 76.4(8) . . ?
N2A Fe1 N2A 78.1(8) . 2_655 ?
N1B Fe1 N1B 170.5(15) . 2_655 ?
N2B Fe1 N3 91.2(5) 2_655 2_655 ?
N2B Fe1 N3 169.1(6) 2_655 . ?
N2B Fe1 N3 91.2(5) . . ?
N2B Fe1 N3 169.1(6) . 2_655 ?
N2B Fe1 N1B 92.4(10) 2_655 . ?
N2B Fe1 N1B 80.5(8) 2_655 2_655 ?
N2B Fe1 N1B 80.5(8) . . ?
N2B Fe1 N1B 92.4(10) . 2_655 ?
N2B Fe1 N2B 83.6(9) . 2_655 ?
C8 N3 Fe1 178.7(7) . . ?
C1A N1A Fe1 114.7(13) . . ?
C5A N1A Fe1 126.8(13) . . ?
C5A N1A C1A 117.6(14) . . ?
N1A C1A C2A 123.6(13) . . ?
N1A C1A C6A 113.8(14) . . ?
C2A C1A C6A 122.5(15) . . ?
C1A C2A H2A 121.6 . . ?
C3A C2A C1A 116.7(13) . . ?
C3A C2A H2A 121.6 . . ?
C2A C3A H3A 118.9 . . ?
C2A C3A C4A 122.2(14) . . ?
C4A C3A H3A 118.9 . . ?
C3A C4A H4A 121.2 . . ?
C3A C4A C5A 117.6(13) . . ?
C5A C4A H4A 121.2 . . ?
N1A C5A C4A 122.2(13) . . ?
N1A C5A H5A 118.9 . . ?
C4A C5A H5A 118.9 . . ?
C1A C6A H6A1 109.9 . . ?
C1A C6A H6A2 109.9 . . ?
H6A1 C6A H6A2 108.3 . . ?
N2A C6A C1A 109.0(12) . . ?
N2A C6A H6A1 109.9 . . ?
N2A C6A H6A2 109.9 . . ?
Fe1 N2A H2A1 112.2 . . ?
C6A N2A Fe1 101.9(14) . . ?
C6A N2A H2A1 112.2 . . ?
C6A N2A C7A 111.7(14) . . ?
C7A N2A Fe1 106.2(15) . . ?
C7A N2A H2A1 112.2 . . ?
N2A C7A C7A 105.2(12) . 2_655 ?
N2A C7A H7A1 110.7 . . ?
N2A C7A H7A2 110.7 . . ?
C7A C7A H7A1 110.7 2_655 . ?
C7A C7A H7A2 110.7 2_655 . ?
H7A1 C7A H7A2 108.8 . . ?
C1B N1B Fe1 115.0(11) . . ?
C5B N1B Fe1 126.6(11) . . ?
C5B N1B C1B 118.4(12) . . ?
N1B C1B C2B 120.6(11) . . ?
N1B C1B C6B 115.7(12) . . ?
C2B C1B C6B 123.7(14) . . ?
C1B C2B H2B 120.6 . . ?
C3B C2B C1B 118.9(12) . . ?
C3B C2B H2B 120.6 . . ?
C2B C3B H3B 118.8 . . ?
C2B C3B C4B 122.4(13) . . ?
C4B C3B H3B 118.8 . . ?
C3B C4B H4B 122.0 . . ?
C3B C4B C5B 116.0(11) . . ?
C5B C4B H4B 122.0 . . ?
N1B C5B C4B 123.8(12) . . ?
N1B C5B H5B 118.1 . . ?
C4B C5B H5B 118.1 . . ?
C1B C6B H6B1 109.1 . . ?
C1B C6B H6B2 109.1 . . ?
H6B1 C6B H6B2 107.8 . . ?
N2B C6B C1B 112.5(13) . . ?
N2B C6B H6B1 109.1 . . ?
N2B C6B H6B2 109.1 . . ?
Fe1 N2B H2B1 107.1 . . ?
C6B N2B Fe1 112.0(13) . . ?
C6B N2B H2B1 107.1 . . ?
C6B N2B C7B 114.5(15) . . ?
C7B N2B Fe1 108.6(13) . . ?
C7B N2B H2B1 107.1 . . ?
N2B C7B C7B 106.0(11) . 2_655 ?
N2B C7B H7B1 110.5 . . ?
N2B C7B H7B2 110.5 . . ?
C7B C7B H7B1 110.5 2_655 . ?
C7B C7B H7B2 110.5 2_655 . ?
H7B1 C7B H7B2 108.7 . . ?

####################################################################### 
# 
# 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_2_298K
_database_code_depnum_ccdc_archive 'CCDC 1414295'
_audit_update_record             
;
2015-10-25 deposited with the CCDC.
2015-10-28 downloaded from the CCDC.
;
#*************************************************************************

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H20 Fe N6 O3'
_chemical_formula_sum            'C16 H20 Fe N6 O3'
_chemical_formula_weight         400.23

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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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                   7.3852(12)
_cell_length_b                   11.0858(18)
_cell_length_c                   11.912(2)
_cell_angle_alpha                105.378(2)
_cell_angle_beta                 91.266(3)
_cell_angle_gamma                101.044(3)
_cell_volume                     920.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3619
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      28.32

_exptl_crystal_description       column
_exptl_crystal_colour            'dark violet'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.848
_shelx_estimated_absorpt_T_min   0.750
_shelx_estimated_absorpt_T_max   0.842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6400
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Bruker, 2013)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'APEX2 CCD detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6665
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.778
_diffrn_reflns_theta_max         28.460
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4556
_reflns_number_gt                3996
_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       'APEX2 (Bruker, 2011)'
_computing_cell_refinement       APEX2
_computing_data_reduction        APEX2
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    
;
OLEX2 (Dolomanov et al., 2009) and DIAMOND (Brandenburg & Putz, 2005)'
;
_computing_publication_material  OLEX2

_refine_special_details          
;
1. H atoms attached to O and N atoms were located in a difference Fourier 
map. The N-H bond length was restrainted to 0.86(2) ANG with Uiso(H2a) 
= 1.2 Ueq(N2). The O-H bond lengths were restrainted to 0.85(2) ANG 
with Uiso(H) = 1.2 Ueq(parent) and the distances of two H atoms 
within lattice water molecule: equal(0.04 ANG).

2. H atoms attached to C atoms were positioned geometrically and refined 
as a riding model with the isotropic displacement parameters related to 
which they are bonded: Uiso(H) = 1.2 Ueq(parent)
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0486P)²+0.3190P] 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         4556
_refine_ls_number_parameters     256
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0963
_refine_ls_wR_factor_gt          0.0918
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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 0.1633(3) 0.73789(18) 0.76414(17) 0.0396(4) Uani 1 1 d . . . . .
H1 H 0.1067 0.7313 0.6916 0.048 Uiso 1 1 calc R U . . .
C2 C 0.0617(3) 0.6825(2) 0.8401(2) 0.0558(5) Uani 1 1 d . . . . .
H2 H -0.0607 0.6402 0.8191 0.067 Uiso 1 1 calc R U . . .
C3 C 0.1448(4) 0.6908(3) 0.9481(2) 0.0664(7) Uani 1 1 d . . . . .
H3 H 0.0794 0.6534 1.0003 0.080 Uiso 1 1 calc R U . . .
C4 C 0.3252(4) 0.7551(2) 0.97700(19) 0.0562(6) Uani 1 1 d . . . . .
H4 H 0.3835 0.7617 1.0490 0.067 Uiso 1 1 calc R U . . .
C5 C 0.4189(3) 0.80987(18) 0.89777(16) 0.0415(4) Uani 1 1 d . . . . .
C6 C 0.6095(3) 0.8801(2) 0.91621(17) 0.0474(5) Uani 1 1 d . . . . .
H6 H 0.6830 0.8941 0.9847 0.057 Uiso 1 1 calc R U . . .
C7 C 0.8525(3) 0.9924(4) 0.8240(2) 0.0878(11) Uani 1 1 d . . . . .
H7 H 0.9406 1.0232 0.8873 0.105 Uiso 1 1 calc R U . . .
C8 C 0.8840(4) 1.0094(4) 0.7134(3) 0.1036(14) Uani 1 1 d . . . . .
H8 H 0.9980 1.0513 0.6976 0.124 Uiso 1 1 calc R U . . .
C9 C 0.7696(3) 0.8600(2) 0.5209(2) 0.0500(5) Uani 1 1 d . . . . .
H9A H 0.8981 0.8822 0.5048 0.060 Uiso 1 1 calc R U . . .
H9B H 0.6924 0.8559 0.4525 0.060 Uiso 1 1 calc R U . . .
C10 C 0.7326(2) 0.73271(17) 0.54761(18) 0.0391(4) Uani 1 1 d . . . . .
C11 C 0.8136(3) 0.6320(2) 0.4936(2) 0.0509(5) Uani 1 1 d . . . . .
H11 H 0.8948 0.6398 0.4361 0.061 Uiso 1 1 calc R U . . .
C12 C 0.7725(3) 0.51910(19) 0.5260(2) 0.0490(5) Uani 1 1 d . . . . .
H12 H 0.8247 0.4501 0.4900 0.059 Uiso 1 1 calc R U . . .
C13 C 0.6543(3) 0.51048(17) 0.61166(18) 0.0428(4) Uani 1 1 d . . . . .
H13 H 0.6272 0.4364 0.6361 0.051 Uiso 1 1 calc R U . . .
C14 C 0.5762(3) 0.61395(16) 0.66110(16) 0.0372(4) Uani 1 1 d . . . . .
H14 H 0.4954 0.6076 0.7190 0.045 Uiso 1 1 calc R U . . .
C15 C 0.4176(3) 1.03529(17) 0.74257(16) 0.0390(4) Uani 1 1 d . . . . .
C16 C 0.3415(2) 0.83250(15) 0.55288(15) 0.0304(3) Uani 1 1 d . . . . .
Fe1 Fe 0.50655(3) 0.87926(2) 0.69288(2) 0.02989(9) Uani 1 1 d . . . . .
N1 N 0.3391(2) 0.80056(14) 0.78989(12) 0.0337(3) Uani 1 1 d . . . . .
N2 N 0.6675(2) 0.92134(15) 0.82951(14) 0.0396(3) Uani 1 1 d . . . . .
N3 N 0.7283(2) 0.95773(15) 0.62278(15) 0.0403(3) Uani 1 1 d D . . . .
H3A H 0.710(3) 1.0196(18) 0.599(2) 0.048 Uiso 1 1 d D U . . .
N4 N 0.61151(19) 0.72318(13) 0.62956(12) 0.0311(3) Uani 1 1 d . . . . .
N5 N 0.3621(3) 1.12774(17) 0.77518(18) 0.0585(5) Uani 1 1 d . . . . .
N6 N 0.2459(2) 0.80436(15) 0.46776(14) 0.0405(3) Uani 1 1 d . . . . .
O1 O 0.3350(3) 0.4952(2) 0.10659(17) 0.0669(5) Uani 1 1 d D . . . .
H1A H 0.320(4) 0.453(3) 0.0357(16) 0.080 Uiso 1 1 d D U . . .
H2A H 0.182(3) 0.374(3) 0.824(2) 0.080 Uiso 1 1 d D U . . .
O2 O 0.2796(3) 0.37223(18) 0.85919(19) 0.0743(6) Uani 1 1 d D . . . .
H1B H 0.446(3) 0.527(3) 0.119(3) 0.089 Uiso 1 1 d D U . . .
H2B H 0.298(4) 0.298(2) 0.833(3) 0.089 Uiso 1 1 d D U . . .
O3 O 0.9098(3) 0.3499(2) 0.76821(16) 0.0682(5) Uani 1 1 d D . . . .
H3B H 0.862(4) 0.308(3) 0.7021(17) 0.082 Uiso 1 1 d D U . . .
H3C H 0.834(4) 0.387(3) 0.801(2) 0.082 Uiso 1 1 d D 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 N1 1.337(2) . ?
C1 C2 1.381(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.386(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9300 . ?
C5 N1 1.372(2) . ?
C5 C6 1.453(3) . ?
C6 N2 1.286(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.397(4) . ?
C7 N2 1.453(3) . ?
C7 H7 0.9300 . ?
C8 N3 1.477(3) . ?
C8 H8 0.9300 . ?
C9 N3 1.479(3) . ?
C9 C10 1.504(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N4 1.349(2) . ?
C10 C11 1.383(3) . ?
C11 C12 1.387(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.368(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.380(3) . ?
C13 H13 0.9300 . ?
C14 N4 1.342(2) . ?
C14 H14 0.9300 . ?
C15 N5 1.152(3) . ?
C15 Fe1 1.9193(19) . ?
C16 N6 1.158(2) . ?
C16 Fe1 1.9354(17) . ?
Fe1 N2 1.8917(16) . ?
Fe1 N1 1.9521(15) . ?
Fe1 N4 2.0028(14) . ?
Fe1 N3 2.0088(17) . ?
N3 H3A 0.840(16) . ?
O1 H1A 0.843(17) . ?
O1 H1B 0.824(17) . ?
O2 H2A 0.829(17) . ?
O2 H2B 0.835(17) . ?
O3 H3B 0.832(17) . ?
O3 H3C 0.809(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 123.10(18) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C1 C2 C3 119.1(2) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C3 C2 119.0(2) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 119.2(2) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 122.28(19) . . ?
N1 C5 C6 112.49(17) . . ?
C4 C5 C6 125.22(19) . . ?
N2 C6 C5 114.04(17) . . ?
N2 C6 H6 123.0 . . ?
C5 C6 H6 123.0 . . ?
C8 C7 N2 112.8(2) . . ?
C8 C7 H7 123.6 . . ?
N2 C7 H7 123.6 . . ?
C7 C8 N3 117.1(2) . . ?
C7 C8 H8 121.4 . . ?
N3 C8 H8 121.4 . . ?
N3 C9 C10 108.66(16) . . ?
N3 C9 H9A 110.0 . . ?
C10 C9 H9A 110.0 . . ?
N3 C9 H9B 110.0 . . ?
C10 C9 H9B 110.0 . . ?
H9A C9 H9B 108.3 . . ?
N4 C10 C11 121.67(18) . . ?
N4 C10 C9 114.57(15) . . ?
C11 C10 C9 123.76(18) . . ?
C10 C11 C12 119.2(2) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C13 C12 C11 119.25(18) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 118.64(18) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 H13 120.7 . . ?
N4 C14 C13 123.08(18) . . ?
N4 C14 H14 118.5 . . ?
C13 C14 H14 118.5 . . ?
N5 C15 Fe1 177.9(2) . . ?
N6 C16 Fe1 178.58(15) . . ?
N2 Fe1 C15 92.49(7) . . ?
N2 Fe1 C16 178.81(7) . . ?
C15 Fe1 C16 88.55(7) . . ?
N2 Fe1 N1 81.26(7) . . ?
C15 Fe1 N1 91.11(8) . . ?
C16 Fe1 N1 98.15(7) . . ?
N2 Fe1 N4 89.35(6) . . ?
C15 Fe1 N4 174.60(7) . . ?
C16 Fe1 N4 89.67(6) . . ?
N1 Fe1 N4 94.19(6) . . ?
N2 Fe1 N3 84.88(7) . . ?
C15 Fe1 N3 94.25(8) . . ?
C16 Fe1 N3 95.62(7) . . ?
N1 Fe1 N3 165.34(7) . . ?
N4 Fe1 N3 80.85(6) . . ?
C1 N1 C5 117.31(16) . . ?
C1 N1 Fe1 129.01(13) . . ?
C5 N1 Fe1 113.65(13) . . ?
C6 N2 C7 125.46(19) . . ?
C6 N2 Fe1 118.45(14) . . ?
C7 N2 Fe1 115.99(15) . . ?
C8 N3 C9 113.1(2) . . ?
C8 N3 Fe1 109.03(15) . . ?
C9 N3 Fe1 108.66(11) . . ?
C8 N3 H3A 106.2(17) . . ?
C9 N3 H3A 107.1(16) . . ?
Fe1 N3 H3A 112.7(16) . . ?
C14 N4 C10 118.07(15) . . ?
C14 N4 Fe1 127.15(13) . . ?
C10 N4 Fe1 114.77(12) . . ?
H1A O1 H1B 105(2) . . ?
H2A O2 H2B 106(2) . . ?
H3B O3 H3C 107(3) . . ?

_refine_diff_density_max         0.471
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.059

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_Ni_298K
_database_code_depnum_ccdc_archive 'CCDC 1414296'
_audit_update_record             
;
2015-10-25 deposited with the CCDC.
2015-10-28 downloaded from the CCDC.
;
#*************************************************************************


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H24 B2 N6 Ni'
_chemical_formula_sum            'C16 H24 B2 N6 Ni'
_chemical_formula_weight         380.74

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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           41
_space_group_name_H-M_alt        'A b a 2'
_space_group_name_Hall           'A 2 -2ac'

_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'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, z+1/2'

_cell_length_a                   14.329(4)
_cell_length_b                   15.405(4)
_cell_length_c                   9.2136(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2033.8(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1137
_cell_measurement_theta_min      3.88
_cell_measurement_theta_max      21.36

_exptl_crystal_description       block
_exptl_crystal_colour            'light violet'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.964
_shelx_estimated_absorpt_T_min   0.809
_shelx_estimated_absorpt_T_max   0.861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6513
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2013)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5662
_diffrn_reflns_av_unetI/netI     0.0637
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.838
_diffrn_reflns_theta_max         25.356
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             1840
_reflns_number_gt                1244
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.860
_reflns_Friedel_fraction_max     0.979
_reflns_Friedel_fraction_full    0.981

_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       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       APEX2
_computing_data_reduction        APEX2
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    
;
OLEX2 (Dolomanov et al., 2009) and DIAMOND (Brandenburg & Putz, 2005)'
;
_computing_publication_material  OLEX2

_refine_special_details          
;
H2a attached to N2 was located in a difference Fourier map,
and the N-H distance was restrainted to 0.86(2) ANG with Uiso(H2a) = 
1.2 Ueq(N2). The rest H atoms were positioned geometrically and refined 
as a riding model with the isotropic displacement parameters related to 
which they are bonded: Uiso(H) = 1.2 Ueq(parent) for C(H); Uiso(H) = 1.5 
Ueq(parent) for B(H).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0207P)²] 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_abs_structure_details 
;
 Flack x determined using 488 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.03(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1840
_refine_ls_number_parameters     118
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0657
_refine_ls_wR_factor_gt          0.0580
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
B1 B 0.9254(6) 0.2158(4) 0.3123(9) 0.097(3) Uani 1 1 d . . . . .
H1A H 0.9807 0.2303 0.2587 0.146 Uiso 1 1 calc R U . . .
H1B H 0.9023 0.2667 0.3606 0.146 Uiso 1 1 calc R U . . .
H1C H 0.8786 0.1943 0.2469 0.146 Uiso 1 1 calc R U . . .
C1 C 0.8075(4) 0.0074(4) 0.7650(6) 0.0687(15) Uani 1 1 d . . . . .
C2 C 0.7161(5) -0.0133(5) 0.7932(8) 0.095(2) Uani 1 1 d . . . . .
H2 H 0.6799 0.0221 0.8524 0.115 Uiso 1 1 calc R U . . .
C3 C 0.6795(6) -0.0865(6) 0.7329(8) 0.109(3) Uani 1 1 d . . . . .
H3 H 0.6176 -0.1015 0.7502 0.131 Uiso 1 1 calc R U . . .
C4 C 0.7340(4) -0.1374(4) 0.6473(9) 0.0832(19) Uani 1 1 d . . . . .
H4 H 0.7101 -0.1874 0.6047 0.100 Uiso 1 1 calc R U . . .
C5 C 0.8244(4) -0.1134(3) 0.6254(5) 0.0619(17) Uani 1 1 d . . . . .
H5 H 0.8619 -0.1490 0.5686 0.074 Uiso 1 1 calc R U . . .
C6 C 0.8528(5) 0.0884(4) 0.8234(8) 0.094(2) Uani 1 1 d . . . . .
H6A H 0.8375 0.1369 0.7604 0.113 Uiso 1 1 calc R U . . .
H6B H 0.8276 0.1008 0.9188 0.113 Uiso 1 1 calc R U . . .
C7 C 0.9909(6) 0.0428(4) 0.9662(6) 0.116(3) Uani 1 1 d . . . . .
H7A H 1.0481 0.0731 0.9906 0.139 Uiso 1 1 calc R U . . .
H7B H 0.9465 0.0543 1.0434 0.139 Uiso 1 1 calc R U . . .
C8 C 0.9492(4) 0.1438(3) 0.4287(6) 0.0529(13) Uani 1 1 d . . . . .
N1 N 0.8616(3) -0.0419(2) 0.6809(6) 0.0511(10) Uani 1 1 d . . . . .
N2 N 0.9543(6) 0.0806(4) 0.8337(6) 0.0663(17) Uani 1 1 d D . . . .
H2A H 0.978(4) 0.130(2) 0.825(8) 0.080 Uiso 1 1 d D U . . .
N3 N 0.9668(4) 0.0912(4) 0.5110(5) 0.0571(17) Uani 1 1 d . . . . .
Ni1 Ni 1.0000 0.0000 0.6624(2) 0.0446(2) Uani 1 2 d S T P . .


_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
B1 C8 1.580(8) . ?
B1 H1A 0.9600 . ?
B1 H1B 0.9600 . ?
B1 H1C 0.9600 . ?
C1 N1 1.332(7) . ?
C1 C2 1.372(9) . ?
C1 C6 1.506(9) . ?
C2 C3 1.363(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.359(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.362(7) . ?
C4 H4 0.9300 . ?
C5 N1 1.326(5) . ?
C5 H5 0.9300 . ?
C6 N2 1.463(11) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C7 1.345(11) 2_755 ?
C7 N2 1.450(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N3 1.138(7) . ?
N1 Ni1 2.093(4) . ?
N2 Ni1 2.112(6) . ?
N2 H2A 0.83(3) . ?
N3 Ni1 2.037(6) . ?
Ni1 N3 2.037(6) 2_755 ?
Ni1 N1 2.093(4) 2_755 ?
Ni1 N2 2.112(6) 2_755 ?

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
C8 B1 H1A 109.5 . . ?
C8 B1 H1B 109.5 . . ?
H1A B1 H1B 109.5 . . ?
C8 B1 H1C 109.5 . . ?
H1A B1 H1C 109.5 . . ?
H1B B1 H1C 109.5 . . ?
N1 C1 C2 122.2(7) . . ?
N1 C1 C6 115.4(5) . . ?
C2 C1 C6 122.4(7) . . ?
C3 C2 C1 118.9(8) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C4 C3 C2 119.5(7) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 118.4(7) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
N1 C5 C4 123.4(6) . . ?
N1 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
N2 C6 C1 112.5(5) . . ?
N2 C6 H6A 109.1 . . ?
C1 C6 H6A 109.1 . . ?
N2 C6 H6B 109.1 . . ?
C1 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C7 C7 N2 117.6(4) 2_755 . ?
C7 C7 H7A 107.9 2_755 . ?
N2 C7 H7A 107.9 . . ?
C7 C7 H7B 107.9 2_755 . ?
N2 C7 H7B 107.9 . . ?
H7A C7 H7B 107.2 . . ?
N3 C8 B1 179.0(7) . . ?
C5 N1 C1 117.6(5) . . ?
C5 N1 Ni1 127.3(4) . . ?
C1 N1 Ni1 115.0(4) . . ?
C7 N2 C6 116.6(7) . . ?
C7 N2 Ni1 106.3(4) . . ?
C6 N2 Ni1 107.9(4) . . ?
C7 N2 H2A 107(5) . . ?
C6 N2 H2A 109(5) . . ?
Ni1 N2 H2A 110(5) . . ?
C8 N3 Ni1 178.2(5) . . ?
N3 Ni1 N3 93.5(3) . 2_755 ?
N3 Ni1 N1 93.7(2) . 2_755 ?
N3 Ni1 N1 92.7(2) 2_755 2_755 ?
N3 Ni1 N1 92.7(2) . . ?
N3 Ni1 N1 93.7(2) 2_755 . ?
N1 Ni1 N1 170.6(3) 2_755 . ?
N3 Ni1 N2 91.96(16) . . ?
N3 Ni1 N2 171.9(3) 2_755 . ?
N1 Ni1 N2 93.0(3) 2_755 . ?
N1 Ni1 N2 80.0(2) . . ?
N3 Ni1 N2 171.9(3) . 2_755 ?
N3 Ni1 N2 91.96(16) 2_755 2_755 ?
N1 Ni1 N2 80.0(2) 2_755 2_755 ?
N1 Ni1 N2 93.0(3) . 2_755 ?
N2 Ni1 N2 83.3(4) . 2_755 ?

_refine_diff_density_max         0.264
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.043

_shelxl_version_number           2013-4

