# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1558844'
_audit_update_record             
;
2017-06-27 deposited with the CCDC.
2017-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H20 Mn N8 Ni O4'
_chemical_formula_weight         538.08

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

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

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

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

_cell_length_a                   9.856(2)
_cell_length_b                   19.543(5)
_cell_length_c                   11.990(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.105(9)
_cell_angle_gamma                90
_cell_volume                     2139.7(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9909
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      28.07

_exptl_crystal_description       cuboid
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.670
_exptl_crystal_F_000             1100
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    1.516
_shelx_estimated_absorpt_T_min   0.751
_shelx_estimated_absorpt_T_max   0.794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.751
_exptl_absorpt_correction_T_max  0.794
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31229
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.084
_diffrn_reflns_theta_max         28.158
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5195
_reflns_number_gt                4434
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0345P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5195
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_ref         0.0732
_refine_ls_wR_factor_gt          0.0666
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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 0.7397(2) 0.15802(8) 0.93854(17) 0.0372(4) Uani 1 1 d . . . . .
C2 C 0.8095(2) 0.15422(9) 1.06512(18) 0.0432(4) Uani 1 1 d . . . . .
C3 C 0.9493(2) 0.17875(12) 1.1246(2) 0.0563(5) Uani 1 1 d . . . . .
H3 H 0.9916 0.1770 1.2082 0.068 Uiso 1 1 calc R U . . .
C4 C 1.0267(2) 0.20615(13) 1.0595(3) 0.0668(6) Uani 1 1 d . . . . .
H4 H 1.1199 0.2241 1.0993 0.080 Uiso 1 1 calc R U . . .
C5 C 0.9654(2) 0.20669(12) 0.9365(2) 0.0619(6) Uani 1 1 d . . . . .
H5 H 1.0199 0.2232 0.8936 0.074 Uiso 1 1 calc R U . . .
C6 C 0.8215(2) 0.18291(10) 0.87282(19) 0.0456(4) Uani 1 1 d . . . . .
C7 C 0.7675(2) 0.18366(10) 0.7427(2) 0.0493(5) Uani 1 1 d . . . . .
H7 H 0.8357 0.1953 0.7093 0.059 Uiso 1 1 calc R U . . .
C8 C 0.6147(3) 0.17735(12) 0.5387(2) 0.0575(6) Uani 1 1 d . . . . .
H8A H 0.7055 0.1672 0.5282 0.069 Uiso 1 1 calc R U . . .
H8B H 0.5887 0.2244 0.5140 0.069 Uiso 1 1 calc R U . . .
C9 C 0.4967(3) 0.13106(11) 0.4589(2) 0.0622(6) Uani 1 1 d . . . . .
H9A H 0.5135 0.0852 0.4923 0.075 Uiso 1 1 calc R U . . .
H9B H 0.5034 0.1292 0.3803 0.075 Uiso 1 1 calc R U . . .
C10 C 0.3443(3) 0.15314(13) 0.44357(19) 0.0632(6) Uani 1 1 d . . . . .
H10A H 0.3347 0.2020 0.4285 0.076 Uiso 1 1 calc R U . . .
H10B H 0.2742 0.1302 0.3740 0.076 Uiso 1 1 calc R U . . .
C11 C 0.1810(3) 0.11508(12) 0.53122(18) 0.0549(5) Uani 1 1 d . . . . .
H11 H 0.1189 0.1119 0.4507 0.066 Uiso 1 1 calc R U . . .
C12 C 0.1188(2) 0.09401(11) 0.61752(18) 0.0478(4) Uani 1 1 d . . . . .
C13 C -0.0268(2) 0.06885(14) 0.5725(2) 0.0626(6) Uani 1 1 d . . . . .
H13 H -0.0803 0.0697 0.4900 0.075 Uiso 1 1 calc R U . . .
C14 C -0.0902(2) 0.04356(14) 0.6467(2) 0.0653(6) Uani 1 1 d . . . . .
H14 H -0.1860 0.0275 0.6148 0.078 Uiso 1 1 calc R U . . .
C15 C -0.0120(2) 0.04172(12) 0.7697(2) 0.0565(5) Uani 1 1 d . . . . .
H15 H -0.0546 0.0238 0.8207 0.068 Uiso 1 1 calc R U . . .
C16 C 0.1295(2) 0.06655(10) 0.81660(18) 0.0442(4) Uani 1 1 d . . . . .
C17 C 0.1981(2) 0.09424(9) 0.74186(16) 0.0387(4) Uani 1 1 d . . . . .
C18 C 0.7794(3) 0.11770(14) 1.24578(19) 0.0668(6) Uani 1 1 d . . . . .
H18A H 0.8632 0.0880 1.2697 0.100 Uiso 1 1 calc R U . . .
H18B H 0.7058 0.0983 1.2707 0.100 Uiso 1 1 calc R U . . .
H18C H 0.8080 0.1617 1.2829 0.100 Uiso 1 1 calc R U . . .
C19 C 0.1640(3) 0.04256(13) 1.0222(2) 0.0615(6) Uani 1 1 d . . . . .
H19A H 0.0695 0.0623 1.0072 0.092 Uiso 1 1 calc R U . . .
H19B H 0.2302 0.0550 1.1015 0.092 Uiso 1 1 calc R U . . .
H19C H 0.1554 -0.0064 1.0163 0.092 Uiso 1 1 calc R U . . .
Mn1 Mn 0.47094(3) 0.09197(2) 0.97948(2) 0.03393(8) Uani 1 1 d . . . . .
N1 N 0.63858(19) 0.17045(8) 0.66761(15) 0.0441(4) Uani 1 1 d . . . . .
N2 N 0.3097(2) 0.13744(9) 0.55071(14) 0.0481(4) Uani 1 1 d . . . . .
N3 N 0.4169(3) 0.16927(10) 1.0835(2) 0.0757(6) Uani 1 1 d . . . . .
N4 N 0.42497(17) 0.20848(7) 1.15703(14) 0.0388(3) Uani 1 1 d . . . . .
N5 N 0.4260(2) 0.24739(9) 1.23004(16) 0.0580(5) Uani 1 1 d . . . . .
N6 N 0.5052(2) 0.01069(8) 1.11480(15) 0.0519(4) Uani 1 1 d . . . . .
N7 N 0.4932(2) -0.00110(8) 1.20821(15) 0.0560(5) Uani 1 1 d . . . . .
N8 N 0.4828(4) -0.01781(13) 1.29680(19) 0.0914(8) Uani 1 1 d . . . . .
Ni1 Ni 0.46755(3) 0.14931(2) 0.71688(2) 0.03536(7) Uani 1 1 d . . . . .
O1 O 0.60345(13) 0.13689(6) 0.88887(11) 0.0384(3) Uani 1 1 d . . . . .
O2 O 0.33197(13) 0.11780(6) 0.79422(10) 0.0385(3) Uani 1 1 d . . . . .
O3 O 0.72205(17) 0.12526(9) 1.11829(12) 0.0583(4) Uani 1 1 d . . . . .
O4 O 0.21886(16) 0.06749(8) 0.93548(13) 0.0536(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.314(2) . ?
C1 C6 1.409(3) . ?
C1 C2 1.413(3) . ?
C2 O3 1.372(2) . ?
C2 C3 1.377(3) . ?
C3 C4 1.389(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.412(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.447(3) . ?
C7 N1 1.277(3) . ?
C7 H7 0.9300 . ?
C8 N1 1.479(3) . ?
C8 C9 1.500(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.506(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N2 1.480(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N2 1.277(3) . ?
C11 C12 1.447(3) . ?
C11 H11 0.9300 . ?
C12 C17 1.399(3) . ?
C12 C13 1.417(3) . ?
C13 C14 1.358(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.385(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.380(3) . ?
C15 H15 0.9300 . ?
C16 O4 1.365(2) . ?
C16 C17 1.417(3) . ?
C17 O2 1.313(2) . ?
C18 O3 1.424(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 O4 1.427(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
Mn1 N3 2.1498(19) . ?
Mn1 O1 2.1735(13) . ?
Mn1 O2 2.1852(13) . ?
Mn1 N6 2.2040(16) . ?
Mn1 N6 2.3576(17) 3_657 ?
Mn1 O4 2.3861(15) . ?
Mn1 O3 2.4937(16) . ?
N1 Ni1 2.0274(16) . ?
N2 Ni1 2.0275(17) . ?
N3 N4 1.148(2) . ?
N4 N5 1.157(2) . ?
N5 Ni1 2.0775(18) 4_566 ?
N6 N7 1.192(2) . ?
N6 Mn1 2.3576(17) 3_657 ?
N7 N8 1.152(3) . ?
Ni1 O2 1.9892(12) . ?
Ni1 O1 2.0067(13) . ?
Ni1 N5 2.0776(18) 4_565 ?

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 C1 C6 123.87(17) . . ?
O1 C1 C2 118.12(16) . . ?
C6 C1 C2 118.00(17) . . ?
O3 C2 C3 125.69(19) . . ?
O3 C2 C1 112.59(16) . . ?
C3 C2 C1 121.7(2) . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 119.8(2) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 121.8(2) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C5 118.7(2) . . ?
C1 C6 C7 123.45(18) . . ?
C5 C6 C7 117.80(19) . . ?
N1 C7 C6 128.49(18) . . ?
N1 C7 H7 115.8 . . ?
C6 C7 H7 115.8 . . ?
N1 C8 C9 113.08(17) . . ?
N1 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
N1 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C8 C9 C10 113.78(19) . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9B 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
N2 C10 C9 112.33(18) . . ?
N2 C10 H10A 109.1 . . ?
C9 C10 H10A 109.1 . . ?
N2 C10 H10B 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
N2 C11 C12 128.71(18) . . ?
N2 C11 H11 115.6 . . ?
C12 C11 H11 115.6 . . ?
C17 C12 C13 119.1(2) . . ?
C17 C12 C11 122.97(18) . . ?
C13 C12 C11 117.83(19) . . ?
C14 C13 C12 121.7(2) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C13 C14 C15 119.9(2) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C16 C15 C14 119.8(2) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
O4 C16 C15 125.88(19) . . ?
O4 C16 C17 112.39(16) . . ?
C15 C16 C17 121.72(19) . . ?
O2 C17 C12 124.65(17) . . ?
O2 C17 C16 117.66(16) . . ?
C12 C17 C16 117.68(17) . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C19 H19A 109.5 . . ?
O4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N3 Mn1 O1 109.44(7) . . ?
N3 Mn1 O2 103.31(8) . . ?
O1 Mn1 O2 70.32(5) . . ?
N3 Mn1 N6 94.71(8) . . ?
O1 Mn1 N6 134.80(6) . . ?
O2 Mn1 N6 141.14(6) . . ?
N3 Mn1 N6 165.32(8) . 3_657 ?
O1 Mn1 N6 85.23(6) . 3_657 ?
O2 Mn1 N6 81.17(6) . 3_657 ?
N6 Mn1 N6 74.00(7) . 3_657 ?
N3 Mn1 O4 78.73(8) . . ?
O1 Mn1 O4 137.90(5) . . ?
O2 Mn1 O4 67.63(5) . . ?
N6 Mn1 O4 82.92(6) . . ?
N6 Mn1 O4 90.39(6) 3_657 . ?
N3 Mn1 O3 80.19(8) . . ?
O1 Mn1 O3 66.18(5) . . ?
O2 Mn1 O3 134.68(5) . . ?
N6 Mn1 O3 81.84(6) . . ?
N6 Mn1 O3 106.80(7) 3_657 . ?
O4 Mn1 O3 152.77(5) . . ?
C7 N1 C8 116.28(17) . . ?
C7 N1 Ni1 123.50(14) . . ?
C8 N1 Ni1 120.00(14) . . ?
C11 N2 C10 116.71(18) . . ?
C11 N2 Ni1 124.12(14) . . ?
C10 N2 Ni1 119.14(15) . . ?
N4 N3 Mn1 162.6(2) . . ?
N3 N4 N5 176.7(2) . . ?
N4 N5 Ni1 121.83(14) . 4_566 ?
N7 N6 Mn1 142.09(14) . . ?
N7 N6 Mn1 110.43(12) . 3_657 ?
Mn1 N6 Mn1 106.00(7) . 3_657 ?
N8 N7 N6 174.7(2) . . ?
O2 Ni1 O1 77.83(5) . . ?
O2 Ni1 N1 167.65(6) . . ?
O1 Ni1 N1 91.00(6) . . ?
O2 Ni1 N2 91.21(6) . . ?
O1 Ni1 N2 164.71(6) . . ?
N1 Ni1 N2 98.72(7) . . ?
O2 Ni1 N5 94.56(6) . 4_565 ?
O1 Ni1 N5 96.54(7) . 4_565 ?
N1 Ni1 N5 91.91(7) . 4_565 ?
N2 Ni1 N5 94.91(7) . 4_565 ?
C1 O1 Ni1 126.92(11) . . ?
C1 O1 Mn1 127.18(11) . . ?
Ni1 O1 Mn1 105.56(6) . . ?
C17 O2 Ni1 128.04(11) . . ?
C17 O2 Mn1 122.53(11) . . ?
Ni1 O2 Mn1 105.75(6) . . ?
C2 O3 C18 118.46(17) . . ?
C2 O3 Mn1 115.88(11) . . ?
C18 O3 Mn1 125.65(14) . . ?
C16 O4 C19 118.94(17) . . ?
C16 O4 Mn1 116.29(11) . . ?
C19 O4 Mn1 123.78(13) . . ?

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.049

