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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_bi10
_database_code_depnum_ccdc_archive 'CCDC 1981492'
loop_
_audit_author_name
_audit_author_address
'George Kostakis'
;University of Sussex
United Kingdom
;
_audit_update_record             
;
2020-02-03 deposited with the CCDC.	2020-08-19 downloaded from the CCDC.
;
_audit_creation_date             2020-02-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H28 Mn2 N16 O2'
_chemical_formula_sum            'C20 H28 Mn2 N16 O2'
_chemical_formula_weight         634.46
_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'
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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.7803(13)
_cell_length_b                   11.4870(12)
_cell_length_c                   11.5255(15)
_cell_angle_alpha                90
_cell_angle_beta                 103.371(10)
_cell_angle_gamma                90
_cell_volume                     1388.6(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7347
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      26.19
_cell_measurement_theta_min      1.94
_shelx_estimated_absorpt_T_max   0.846
_shelx_estimated_absorpt_T_min   0.736
_exptl_absorpt_coefficient_mu    0.960
_exptl_absorpt_correction_T_max  0.8462
_exptl_absorpt_correction_T_min  0.7361
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'XPREP in SHELXTL 6.14 (BrukerAXS Inc., 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7258
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.613
_diffrn_reflns_theta_min         2.332
_diffrn_ambient_temperature      180.15
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2173
_reflns_number_total             2584
_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       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2584
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0252
_refine_ls_restrained_S_all      1.028
_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)+(0.0476P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0679
_refine_ls_wR_factor_ref         0.0703
_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, All O(H) groups
2. Restrained distances
 O1-H1
 0.88 with sigma of 0.04
3.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
3.b Me refined with riding coordinates:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C6(H6)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.16549(2) -0.00248(2) 0.02670(2) 0.03815(10) Uani 1 1 d . . . . .
O1 O 0.23238(12) 0.03784(11) 0.22133(10) 0.0445(3) Uani 1 1 d D . . . .
H1 H 0.195(2) 0.0836(18) 0.2550(18) 0.067 Uiso 1 1 d DR . . . .
C1 C 0.13402(18) -0.01362(14) -0.26016(15) 0.0486(4) Uani 1 1 d . . . . .
H1A H 0.0638 -0.0630 -0.2586 0.058 Uiso 1 1 calc R . . . .
C2 C 0.1683(2) 0.00425(15) -0.36808(15) 0.0534(4) Uani 1 1 d . . . . .
H2 H 0.1220 -0.0326 -0.4387 0.064 Uiso 1 1 calc R . . . .
C3 C 0.26960(18) 0.07563(16) -0.37148(15) 0.0535(4) Uani 1 1 d . . . . .
H3 H 0.2948 0.0884 -0.4442 0.064 Uiso 1 1 calc R . . . .
C4 C 0.33457(17) 0.12876(15) -0.26680(15) 0.0476(4) Uani 1 1 d . . . . .
H4 H 0.4045 0.1791 -0.2665 0.057 Uiso 1 1 calc R . . . .
C5 C 0.29519(15) 0.10673(13) -0.16304(13) 0.0400(3) Uani 1 1 d . . . . .
C6 C 0.36450(16) 0.15417(13) -0.04704(13) 0.0420(3) Uani 1 1 d . . . . .
H6 H 0.4349 0.2051 -0.0424 0.050 Uiso 1 1 calc R . . . .
C7 C 0.39334(15) 0.16575(13) 0.16679(13) 0.0411(3) Uani 1 1 d . . . . .
C8 C 0.36429(16) 0.06992(15) 0.25001(14) 0.0458(4) Uani 1 1 d . . . . .
H8A H 0.4167 0.0005 0.2437 0.055 Uiso 1 1 calc R . . . .
H8B H 0.3882 0.0979 0.3335 0.055 Uiso 1 1 calc R . . . .
C9 C 0.33363(18) 0.28165(14) 0.19023(15) 0.0484(4) Uani 1 1 d . . . . .
H9A H 0.2412 0.2721 0.1784 0.073 Uiso 1 1 calc R . . . .
H9B H 0.3515 0.3407 0.1349 0.073 Uiso 1 1 calc R . . . .
H9C H 0.3700 0.3065 0.2724 0.073 Uiso 1 1 calc R . . . .
C10 C 0.53704(17) 0.17831(16) 0.18466(16) 0.0522(4) Uani 1 1 d . . . . .
H10A H 0.5737 0.1035 0.1691 0.078 Uiso 1 1 calc R . . . .
H10B H 0.5742 0.2025 0.2669 0.078 Uiso 1 1 calc R . . . .
H10C H 0.5557 0.2371 0.1294 0.078 Uiso 1 1 calc R . . . .
N1 N 0.19622(13) 0.03610(11) -0.15904(11) 0.0408(3) Uani 1 1 d . . . . .
N2 N 0.32854(12) 0.12585(11) 0.04591(11) 0.0387(3) Uani 1 1 d . . . . .
N3 N 0.29265(16) -0.14974(13) 0.04421(14) 0.0545(4) Uani 1 1 d . . . . .
N4 N 0.33735(12) -0.23226(12) 0.09499(11) 0.0399(3) Uani 1 1 d . . . . .
N5 N 0.38574(15) -0.31648(14) 0.14247(14) 0.0554(4) Uani 1 1 d . . . . .
N6 N 0.00277(12) 0.11819(13) 0.01576(12) 0.0457(3) Uani 1 1 d . . . . .
N7 N 0.00733(13) 0.22040(13) 0.02303(11) 0.0444(3) Uani 1 1 d . . . . .
N8 N 0.01288(17) 0.32109(14) 0.03067(16) 0.0631(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 O1 2.2402(12) . ?
Mn1 N1 2.2841(13) . ?
Mn1 N2 2.2654(13) . ?
Mn1 N3 2.1571(15) . ?
Mn1 N6 2.2164(14) . ?
Mn1 N6 2.2103(14) 3 ?
O1 H1 0.812(19) . ?
O1 C8 1.432(2) . ?
C1 H1A 0.9500 . ?
C1 C2 1.392(3) . ?
C1 N1 1.331(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.374(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.382(2) . ?
C5 C6 1.477(2) . ?
C5 N1 1.350(2) . ?
C6 H6 0.9500 . ?
C6 N2 1.263(2) . ?
C7 C8 1.539(2) . ?
C7 C9 1.530(2) . ?
C7 C10 1.522(2) . ?
C7 N2 1.4795(19) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
N3 N4 1.1588(19) . ?
N4 N5 1.1728(19) . ?
N6 Mn1 2.2103(14) 3 ?
N6 N7 1.177(2) . ?
N7 N8 1.161(2) . ?

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
O1 Mn1 N1 144.64(5) . . ?
O1 Mn1 N2 72.83(4) . . ?
N2 Mn1 N1 71.81(5) . . ?
N3 Mn1 O1 91.03(5) . . ?
N3 Mn1 N1 90.75(5) . . ?
N3 Mn1 N2 92.25(6) . . ?
N3 Mn1 N6 166.72(6) . . ?
N3 Mn1 N6 91.17(6) . 3 ?
N6 Mn1 O1 89.71(5) . . ?
N6 Mn1 O1 113.81(5) 3 . ?
N6 Mn1 N1 96.30(5) . . ?
N6 Mn1 N1 101.46(5) 3 . ?
N6 Mn1 N2 172.49(5) 3 . ?
N6 Mn1 N2 100.64(5) . . ?
N6 Mn1 N6 76.43(6) 3 . ?
Mn1 O1 H1 122.2(15) . . ?
C8 O1 Mn1 110.91(9) . . ?
C8 O1 H1 107.3(16) . . ?
C2 C1 H1A 118.8 . . ?
N1 C1 H1A 118.8 . . ?
N1 C1 C2 122.34(17) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.37(16) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.83(16) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.51(16) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 C6 121.57(15) . . ?
N1 C5 C4 122.90(15) . . ?
N1 C5 C6 115.43(13) . . ?
C5 C6 H6 120.6 . . ?
N2 C6 C5 118.84(15) . . ?
N2 C6 H6 120.6 . . ?
C9 C7 C8 110.96(13) . . ?
C10 C7 C8 109.33(14) . . ?
C10 C7 C9 110.51(14) . . ?
N2 C7 C8 104.21(12) . . ?
N2 C7 C9 108.03(13) . . ?
N2 C7 C10 113.64(13) . . ?
O1 C8 C7 112.00(13) . . ?
O1 C8 H8A 109.2 . . ?
O1 C8 H8B 109.2 . . ?
C7 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C1 N1 Mn1 125.76(11) . . ?
C1 N1 C5 118.04(14) . . ?
C5 N1 Mn1 115.83(10) . . ?
C6 N2 Mn1 117.91(10) . . ?
C6 N2 C7 123.24(14) . . ?
C7 N2 Mn1 118.71(9) . . ?
N4 N3 Mn1 150.43(13) . . ?
N3 N4 N5 176.93(16) . . ?
Mn1 N6 Mn1 103.57(6) 3 . ?
N7 N6 Mn1 126.88(11) . . ?
N7 N6 Mn1 129.36(11) . 3 ?
N8 N7 N6 179.44(19) . . ?

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
O1 H1 N5 0.812(19) 1.99(2) 2.7948(19) 172(2) 2

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

data_bi43fin
_database_code_depnum_ccdc_archive 'CCDC 1981493'
loop_
_audit_author_name
_audit_author_address
'George Kostakis'
;University of Sussex
United Kingdom
;
_audit_update_record             
;
2020-02-03 deposited with the CCDC.	2020-08-19 downloaded from the CCDC.
;
_audit_creation_date             2020-02-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H28 N16 Ni2 O2, 2(C3 H7 N O)'
_chemical_formula_sum            'C26 H42 N18 Ni2 O4'
_chemical_formula_weight         788.19
_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'
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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.6224(9)
_cell_length_b                   16.354(2)
_cell_length_c                   10.1679(10)
_cell_angle_alpha                90
_cell_angle_beta                 104.008(7)
_cell_angle_gamma                90
_cell_volume                     1875.2(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2772
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.07
_cell_measurement_theta_min      1.80
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.866
_exptl_absorpt_coefficient_mu    1.061
_exptl_absorpt_correction_T_max  0.9489
_exptl_absorpt_correction_T_min  0.8657
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'XPREP in SHELXTL 6.14 (BrukerAXS Inc., 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0663
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9067
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.645
_diffrn_reflns_theta_min         2.491
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2100
_reflns_number_total             3513
_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       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.881
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3513
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0378
_refine_ls_restrained_S_all      0.881
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0212P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0562
_refine_ls_wR_factor_ref         0.0664
_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, All O(H) groups
2. Restrained distances
 O1-H1
 0.88 with sigma of 0.04
3.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
3.b Me refined with riding coordinates:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C6(H6), C11(H11)
;
_atom_sites_solution_hydrogens   mixed
_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
Ni1 Ni 0.62049(3) 0.05100(2) 0.50425(4) 0.05772(13) Uani 1 1 d . . . . .
O1 O 0.72637(17) -0.05099(15) 0.4669(2) 0.0711(6) Uani 1 1 d D . . . .
H1 H 0.739(3) -0.085(2) 0.530(3) 0.107 Uiso 1 1 d DR . . . .
O2 O 0.7873(2) -0.15175(18) 0.6697(3) 0.1048(9) Uani 1 1 d . . . . .
N1 N 0.5565(2) 0.17081(16) 0.4883(3) 0.0615(7) Uani 1 1 d . . . . .
N2 N 0.70832(19) 0.09943(16) 0.3737(2) 0.0585(6) Uani 1 1 d . . . . .
N3 N 0.7589(2) 0.08189(19) 0.6713(3) 0.0793(9) Uani 1 1 d . . . . .
N4 N 0.8112(2) 0.1423(2) 0.6720(3) 0.0759(8) Uani 1 1 d . . . . .
N5 N 0.8605(3) 0.2044(2) 0.6720(4) 0.1228(13) Uani 1 1 d . . . . .
N6 N 0.5293(2) -0.00168(16) 0.6321(2) 0.0631(7) Uani 1 1 d . . . . .
N7 N 0.5700(2) -0.01668(15) 0.7497(3) 0.0599(6) Uani 1 1 d . . . . .
N8 N 0.6091(2) -0.02866(19) 0.8624(3) 0.0890(10) Uani 1 1 d . . . . .
N9 N 0.8719(3) -0.1695(3) 0.8899(4) 0.1079(11) Uani 1 1 d . . . . .
C1 C 0.4771(3) 0.2044(2) 0.5460(3) 0.0706(9) Uani 1 1 d . . . . .
H1A H 0.4367 0.1711 0.5940 0.085 Uiso 1 1 calc R . . . .
C2 C 0.4524(3) 0.2875(2) 0.5369(4) 0.0789(10) Uani 1 1 d . . . . .
H2 H 0.3970 0.3095 0.5794 0.095 Uiso 1 1 calc R . . . .
C3 C 0.5104(3) 0.3367(2) 0.4647(4) 0.0777(10) Uani 1 1 d . . . . .
H3 H 0.4945 0.3925 0.4572 0.093 Uiso 1 1 calc R . . . .
C4 C 0.5926(3) 0.3024(2) 0.4035(4) 0.0743(9) Uani 1 1 d . . . . .
H4 H 0.6333 0.3347 0.3545 0.089 Uiso 1 1 calc R . . . .
C5 C 0.6133(3) 0.2193(2) 0.4163(3) 0.0621(8) Uani 1 1 d . . . . .
C6 C 0.6986(3) 0.1760(2) 0.3560(3) 0.0656(8) Uani 1 1 d . . . . .
H6 H 0.7440 0.2038 0.3067 0.079 Uiso 1 1 calc R . . . .
C7 C 0.7898(2) 0.0460(2) 0.3225(3) 0.0645(8) Uani 1 1 d . . . . .
C8 C 0.7180(3) 0.0063(2) 0.1920(3) 0.0914(11) Uani 1 1 d . . . . .
H8A H 0.6934 0.0475 0.1238 0.137 Uiso 1 1 calc R . . . .
H8B H 0.6494 -0.0201 0.2094 0.137 Uiso 1 1 calc R . . . .
H8C H 0.7662 -0.0334 0.1610 0.137 Uiso 1 1 calc R . . . .
C9 C 0.8987(3) 0.0905(2) 0.2984(4) 0.0903(11) Uani 1 1 d . . . . .
H9A H 0.8740 0.1307 0.2285 0.135 Uiso 1 1 calc R . . . .
H9B H 0.9504 0.0518 0.2710 0.135 Uiso 1 1 calc R . . . .
H9C H 0.9400 0.1169 0.3806 0.135 Uiso 1 1 calc R . . . .
C10 C 0.8297(3) -0.0176(2) 0.4331(3) 0.0719(9) Uani 1 1 d . . . . .
H10A H 0.8737 -0.0607 0.4015 0.086 Uiso 1 1 calc R . . . .
H10B H 0.8809 0.0074 0.5125 0.086 Uiso 1 1 calc R . . . .
C11 C 0.8314(3) -0.1247(3) 0.7827(5) 0.0946(12) Uani 1 1 d . . . . .
H11 H 0.8364 -0.0682 0.7930 0.114 Uiso 1 1 calc R . . . .
C12 C 0.8602(5) -0.2582(4) 0.8794(6) 0.156(2) Uani 1 1 d . . . . .
H12A H 0.8180 -0.2727 0.7892 0.234 Uiso 1 1 calc R . . . .
H12B H 0.8173 -0.2775 0.9430 0.234 Uiso 1 1 calc R . . . .
H12C H 0.9376 -0.2826 0.8992 0.234 Uiso 1 1 calc R . . . .
C13 C 0.9322(6) -0.1339(5) 1.0181(6) 0.203(3) Uani 1 1 d . . . . .
H13A H 0.9320 -0.0754 1.0100 0.304 Uiso 1 1 calc R . . . .
H13B H 1.0125 -0.1533 1.0430 0.304 Uiso 1 1 calc R . . . .
H13C H 0.8921 -0.1494 1.0865 0.304 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
Ni1 O1 2.160(2) . ?
Ni1 N1 2.088(3) . ?
Ni1 N2 2.022(3) . ?
Ni1 N3 2.099(3) . ?
Ni1 N6 2.105(2) 3_656 ?
Ni1 N6 2.055(3) . ?
O1 H1 0.84(3) . ?
O1 C10 1.434(4) . ?
O2 C11 1.223(5) . ?
N1 C1 1.327(4) . ?
N1 C5 1.354(4) . ?
N2 C6 1.266(4) . ?
N2 C7 1.473(4) . ?
N3 N4 1.158(4) . ?
N4 N5 1.166(4) . ?
N6 Ni1 2.105(2) 3_656 ?
N6 N7 1.200(3) . ?
N7 N8 1.143(3) . ?
N9 C11 1.303(5) . ?
N9 C12 1.458(6) . ?
N9 C13 1.445(6) . ?
C1 H1A 0.9300 . ?
C1 C2 1.387(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.372(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(4) . ?
C5 C6 1.468(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.531(4) . ?
C7 C9 1.530(4) . ?
C7 C10 1.520(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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 Ni1 O1 156.65(10) . . ?
N1 Ni1 N3 91.47(10) . . ?
N1 Ni1 N6 94.95(9) . 3_656 ?
N2 Ni1 O1 77.72(10) . . ?
N2 Ni1 N1 78.95(11) . . ?
N2 Ni1 N3 91.55(10) . . ?
N2 Ni1 N6 100.72(9) . 3_656 ?
N2 Ni1 N6 177.91(10) . . ?
N3 Ni1 O1 88.31(10) . . ?
N3 Ni1 N6 167.04(11) . 3_656 ?
N6 Ni1 O1 100.99(10) . . ?
N6 Ni1 O1 90.21(9) 3_656 . ?
N6 Ni1 N1 102.36(11) . . ?
N6 Ni1 N3 90.06(10) . . ?
N6 Ni1 N6 77.58(10) . 3_656 ?
Ni1 O1 H1 113(3) . . ?
C10 O1 Ni1 107.10(19) . . ?
C10 O1 H1 116(3) . . ?
C1 N1 Ni1 128.8(2) . . ?
C1 N1 C5 118.7(3) . . ?
C5 N1 Ni1 112.4(2) . . ?
C6 N2 Ni1 116.0(2) . . ?
C6 N2 C7 125.4(3) . . ?
C7 N2 Ni1 118.0(2) . . ?
N4 N3 Ni1 120.5(2) . . ?
N3 N4 N5 177.9(4) . . ?
Ni1 N6 Ni1 102.42(10) . 3_656 ?
N7 N6 Ni1 129.9(2) . 3_656 ?
N7 N6 Ni1 125.21(19) . . ?
N8 N7 N6 178.1(3) . . ?
C11 N9 C12 119.4(5) . . ?
C11 N9 C13 121.7(5) . . ?
C13 N9 C12 118.9(5) . . ?
N1 C1 H1A 119.0 . . ?
N1 C1 C2 122.0(3) . . ?
C2 C1 H1A 119.0 . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.4(4) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.1(3) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.8(4) . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 122.0(3) . . ?
N1 C5 C6 114.2(3) . . ?
C4 C5 C6 123.8(3) . . ?
N2 C6 C5 117.7(3) . . ?
N2 C6 H6 121.2 . . ?
C5 C6 H6 121.2 . . ?
N2 C7 C8 107.2(2) . . ?
N2 C7 C9 113.7(3) . . ?
N2 C7 C10 104.6(2) . . ?
C9 C7 C8 111.2(3) . . ?
C10 C7 C8 110.8(3) . . ?
C10 C7 C9 109.2(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 C7 108.4(2) . . ?
O1 C10 H10A 110.0 . . ?
O1 C10 H10B 110.0 . . ?
C7 C10 H10A 110.0 . . ?
C7 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
O2 C11 N9 124.5(5) . . ?
O2 C11 H11 117.7 . . ?
N9 C11 H11 117.7 . . ?
N9 C12 H12A 109.5 . . ?
N9 C12 H12B 109.5 . . ?
N9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N9 C13 H13A 109.5 . . ?
N9 C13 H13B 109.5 . . ?
N9 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.84(3) 1.77(3) 2.600(3) 172(4) .

_olex2_submission_special_instructions 'No special instructions were received'
