# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

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

data_Complex1
_database_code_depnum_ccdc_archive 'CCDC 1525977'
_audit_update_record             
;
2018-05-09 deposited with the CCDC.	2019-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H19 Cl2 Co N3 O3'
_chemical_formula_weight         467.20

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.0135(10)
_cell_length_b                   13.7499(12)
_cell_length_c                   13.7117(12)
_cell_angle_alpha                90
_cell_angle_beta                 102.969(2)
_cell_angle_gamma                90
_cell_volume                     2023.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      25.50

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_F_000             956
_exptl_transmission_factor_min   0.751
_exptl_transmission_factor_max   0.843
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.137
_shelx_estimated_absorpt_T_min   0.727
_shelx_estimated_absorpt_T_max   0.848
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER SMART APEX'
_diffrn_measurement_method       /w-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17578
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.963
_diffrn_reflns_theta_max         25.046
_diffrn_reflns_theta_full        25.047
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3576
_reflns_number_gt                2822
_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       'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45 ( Bruker, 2003)'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'DIAMOND 2.1e'
_computing_publication_material  SHELXL

_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)+(0.0358P)²+1.9740P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3576
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0952
_refine_ls_wR_factor_gt          0.0861
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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
Co1 Co 0.31385(4) 0.68907(3) 0.71663(3) 0.03190(13) Uani 1 1 d . . . . .
Cl1 Cl 0.36705(8) 0.80005(7) 0.85653(7) 0.0589(3) Uani 1 1 d . . . . .
Cl2 Cl 0.65527(9) 0.51664(8) 0.86483(7) 0.0634(3) Uani 1 1 d . . . . .
O1 O 0.1584(2) 0.77247(18) 0.63972(17) 0.0456(6) Uani 1 1 d . . . . .
O2 O 0.3856(2) 0.56134(18) 0.79629(18) 0.0468(6) Uani 1 1 d . . . . .
N2 N 0.4668(2) 0.73083(18) 0.65553(18) 0.0335(6) Uani 1 1 d . . . . .
N3 N 0.1658(2) 0.63445(18) 0.76943(18) 0.0350(6) Uani 1 1 d . . . . .
N1 N 0.2854(2) 0.60290(18) 0.58159(18) 0.0340(6) Uani 1 1 d . . . . .
O1W O 0.1365(3) 0.7762(2) 0.4485(2) 0.0732(8) Uani 1 1 d G . . . .
H1WA H 0.152708 0.833735 0.432445 0.110 Uiso 1 1 d G U . . .
H1WB H 0.059692 0.764274 0.425433 0.110 Uiso 1 1 d G U . . .
C12 C 0.3729(3) 0.6196(2) 0.5267(2) 0.0308(7) Uani 1 1 d . . . . .
C11 C 0.4710(3) 0.6862(2) 0.5673(2) 0.0307(6) Uani 1 1 d . . . . .
C14 C 0.0531(3) 0.6743(2) 0.7407(2) 0.0399(8) Uani 1 1 d . . . . .
C4 C 0.3696(3) 0.5738(2) 0.4347(2) 0.0375(7) Uani 1 1 d . . . . .
C7 C 0.5671(3) 0.7031(2) 0.5167(2) 0.0393(8) Uani 1 1 d . . . . .
C1 C 0.1950(3) 0.5412(2) 0.5453(3) 0.0436(8) Uani 1 1 d . . . . .
H1A H 0.136399 0.527956 0.582883 0.052 Uiso 1 1 calc R U . . .
C6 C 0.5625(3) 0.6529(3) 0.4242(3) 0.0466(9) Uani 1 1 d . . . . .
H6 H 0.626310 0.662394 0.390767 0.056 Uiso 1 1 calc R U . . .
C5 C 0.4687(3) 0.5929(3) 0.3848(2) 0.0470(9) Uani 1 1 d . . . . .
H5 H 0.467702 0.562817 0.323862 0.056 Uiso 1 1 calc R U . . .
C18 C 0.1870(3) 0.5629(2) 0.8369(2) 0.0426(8) Uani 1 1 d . . . . .
C10 C 0.5579(3) 0.7925(2) 0.6937(3) 0.0457(8) Uani 1 1 d . . . . .
H10 H 0.555655 0.823802 0.753367 0.055 Uiso 1 1 calc R U . . .
C2 C 0.1830(3) 0.4950(3) 0.4532(3) 0.0526(9) Uani 1 1 d . . . . .
H2A H 0.116701 0.453036 0.429726 0.063 Uiso 1 1 calc R U . . .
C3 C 0.2698(3) 0.5120(3) 0.3977(3) 0.0484(9) Uani 1 1 d . . . . .
H3 H 0.262200 0.482303 0.335655 0.058 Uiso 1 1 calc R U . . .
C8 C 0.6608(3) 0.7687(3) 0.5602(3) 0.0502(9) Uani 1 1 d . . . . .
H8 H 0.725462 0.782334 0.528853 0.060 Uiso 1 1 calc R U . . .
C13 C 0.0412(3) 0.7541(3) 0.6637(3) 0.0523(9) Uani 1 1 d . . . . .
H13A H -0.019106 0.735189 0.603702 0.063 Uiso 1 1 calc R U . . .
H13B H 0.011425 0.812952 0.689627 0.063 Uiso 1 1 calc R U . . .
C15 C -0.0451(3) 0.6433(3) 0.7813(3) 0.0552(10) Uani 1 1 d . . . . .
H15 H -0.123341 0.672003 0.762394 0.066 Uiso 1 1 calc R U . . .
C9 C 0.6570(3) 0.8125(3) 0.6484(3) 0.0535(9) Uani 1 1 d . . . . .
H9 H 0.719635 0.855369 0.678367 0.064 Uiso 1 1 calc R U . . .
C17 C 0.0924(4) 0.5279(3) 0.8794(3) 0.0580(10) Uani 1 1 d . . . . .
H17 H 0.107426 0.478089 0.926426 0.070 Uiso 1 1 calc R U . . .
C16 C -0.0233(4) 0.5687(3) 0.8505(3) 0.0642(12) Uani 1 1 d . . . . .
H16 H -0.088076 0.545865 0.877613 0.077 Uiso 1 1 calc R U . . .
C19 C 0.3183(4) 0.5255(3) 0.8651(3) 0.0590(10) Uani 1 1 d . . . . .
H19A H 0.357586 0.546700 0.932205 0.071 Uiso 1 1 calc R U . . .
H19B H 0.318091 0.454937 0.864056 0.071 Uiso 1 1 calc R U . . .
H1 H 0.148(5) 0.776(4) 0.584(3) 0.089 Uiso 1 1 d . U . . .
H2 H 0.459(4) 0.547(3) 0.814(3) 0.089 Uiso 1 1 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
Co1 N3 2.068(2) . ?
Co1 N2 2.122(2) . ?
Co1 O2 2.125(2) . ?
Co1 O1 2.132(2) . ?
Co1 N1 2.161(2) . ?
Co1 Cl1 2.4181(10) . ?
O1 C13 1.425(4) . ?
O1 H1 0.75(5) . ?
O2 C19 1.413(4) . ?
O2 H2 0.81(4) . ?
N2 C10 1.327(4) . ?
N2 C11 1.367(4) . ?
N3 C14 1.333(4) . ?
N3 C18 1.335(4) . ?
N1 C1 1.318(4) . ?
N1 C12 1.368(4) . ?
O1W H1WA 0.8500 . ?
O1W H1WB 0.8500 . ?
C12 C4 1.403(4) . ?
C12 C11 1.430(4) . ?
C11 C7 1.408(4) . ?
C14 C15 1.390(5) . ?
C14 C13 1.507(5) . ?
C4 C3 1.393(5) . ?
C4 C5 1.436(4) . ?
C7 C8 1.399(5) . ?
C7 C6 1.435(5) . ?
C1 C2 1.392(5) . ?
C1 H1A 0.9300 . ?
C6 C5 1.338(5) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?
C18 C17 1.388(5) . ?
C18 C19 1.502(5) . ?
C10 C9 1.399(5) . ?
C10 H10 0.9300 . ?
C2 C3 1.370(5) . ?
C2 H2A 0.9300 . ?
C3 H3 0.9300 . ?
C8 C9 1.361(5) . ?
C8 H8 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C15 C16 1.381(6) . ?
C15 H15 0.9300 . ?
C9 H9 0.9300 . ?
C17 C16 1.367(6) . ?
C17 H17 0.9300 . ?
C16 H16 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 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
N3 Co1 N2 174.07(10) . . ?
N3 Co1 O2 75.61(9) . . ?
N2 Co1 O2 100.94(9) . . ?
N3 Co1 O1 76.12(9) . . ?
N2 Co1 O1 106.23(9) . . ?
O2 Co1 O1 149.72(9) . . ?
N3 Co1 N1 97.29(9) . . ?
N2 Co1 N1 77.60(9) . . ?
O2 Co1 N1 87.30(9) . . ?
O1 Co1 N1 85.72(9) . . ?
N3 Co1 Cl1 91.21(7) . . ?
N2 Co1 Cl1 94.01(7) . . ?
O2 Co1 Cl1 96.77(8) . . ?
O1 Co1 Cl1 94.45(7) . . ?
N1 Co1 Cl1 171.27(7) . . ?
C13 O1 Co1 117.3(2) . . ?
C13 O1 H1 108(4) . . ?
Co1 O1 H1 117(4) . . ?
C19 O2 Co1 116.18(19) . . ?
C19 O2 H2 111(3) . . ?
Co1 O2 H2 126(3) . . ?
C10 N2 C11 117.6(3) . . ?
C10 N2 Co1 127.8(2) . . ?
C11 N2 Co1 114.54(18) . . ?
C14 N3 C18 120.9(3) . . ?
C14 N3 Co1 120.1(2) . . ?
C18 N3 Co1 118.8(2) . . ?
C1 N1 C12 117.8(3) . . ?
C1 N1 Co1 128.9(2) . . ?
C12 N1 Co1 113.25(19) . . ?
H1WA O1W H1WB 109.5 . . ?
N1 C12 C4 122.7(3) . . ?
N1 C12 C11 117.2(3) . . ?
C4 C12 C11 120.1(3) . . ?
N2 C11 C7 122.7(3) . . ?
N2 C11 C12 117.3(2) . . ?
C7 C11 C12 120.0(3) . . ?
N3 C14 C15 120.8(3) . . ?
N3 C14 C13 115.8(3) . . ?
C15 C14 C13 123.4(3) . . ?
C3 C4 C12 117.4(3) . . ?
C3 C4 C5 124.0(3) . . ?
C12 C4 C5 118.6(3) . . ?
C8 C7 C11 117.4(3) . . ?
C8 C7 C6 124.3(3) . . ?
C11 C7 C6 118.3(3) . . ?
N1 C1 C2 123.1(3) . . ?
N1 C1 H1A 118.5 . . ?
C2 C1 H1A 118.5 . . ?
C5 C6 C7 121.6(3) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
N3 C18 C17 121.0(3) . . ?
N3 C18 C19 116.0(3) . . ?
C17 C18 C19 122.9(3) . . ?
N2 C10 C9 123.1(3) . . ?
N2 C10 H10 118.4 . . ?
C9 C10 H10 118.4 . . ?
C3 C2 C1 119.4(3) . . ?
C3 C2 H2A 120.3 . . ?
C1 C2 H2A 120.3 . . ?
C2 C3 C4 119.6(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C9 C8 C7 119.8(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
O1 C13 C14 110.5(3) . . ?
O1 C13 H13A 109.6 . . ?
C14 C13 H13A 109.6 . . ?
O1 C13 H13B 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C16 C15 C14 118.1(3) . . ?
C16 C15 H15 120.9 . . ?
C14 C15 H15 120.9 . . ?
C8 C9 C10 119.3(3) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C16 C17 C18 118.3(4) . . ?
C16 C17 H17 120.8 . . ?
C18 C17 H17 120.8 . . ?
C17 C16 C15 120.7(3) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
O2 C19 C18 109.2(3) . . ?
O2 C19 H19A 109.8 . . ?
C18 C19 H19A 109.8 . . ?
O2 C19 H19B 109.8 . . ?
C18 C19 H19B 109.8 . . ?
H19A C19 H19B 108.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 C12 C4 -0.2(4) . . . . ?
Co1 N1 C12 C4 -177.8(2) . . . . ?
C1 N1 C12 C11 -179.6(3) . . . . ?
Co1 N1 C12 C11 2.8(3) . . . . ?
C10 N2 C11 C7 0.0(4) . . . . ?
Co1 N2 C11 C7 -178.7(2) . . . . ?
C10 N2 C11 C12 179.8(3) . . . . ?
Co1 N2 C11 C12 1.1(3) . . . . ?
N1 C12 C11 N2 -2.7(4) . . . . ?
C4 C12 C11 N2 177.9(3) . . . . ?
N1 C12 C11 C7 177.1(3) . . . . ?
C4 C12 C11 C7 -2.3(4) . . . . ?
C18 N3 C14 C15 0.9(5) . . . . ?
Co1 N3 C14 C15 -175.1(2) . . . . ?
C18 N3 C14 C13 -179.7(3) . . . . ?
Co1 N3 C14 C13 4.3(4) . . . . ?
N1 C12 C4 C3 2.4(5) . . . . ?
C11 C12 C4 C3 -178.2(3) . . . . ?
N1 C12 C4 C5 -177.3(3) . . . . ?
C11 C12 C4 C5 2.1(4) . . . . ?
N2 C11 C7 C8 0.0(4) . . . . ?
C12 C11 C7 C8 -179.8(3) . . . . ?
N2 C11 C7 C6 -179.7(3) . . . . ?
C12 C11 C7 C6 0.5(4) . . . . ?
C12 N1 C1 C2 -1.8(5) . . . . ?
Co1 N1 C1 C2 175.4(3) . . . . ?
C8 C7 C6 C5 -178.2(3) . . . . ?
C11 C7 C6 C5 1.4(5) . . . . ?
C7 C6 C5 C4 -1.6(5) . . . . ?
C3 C4 C5 C6 -179.8(3) . . . . ?
C12 C4 C5 C6 -0.2(5) . . . . ?
C14 N3 C18 C17 -0.2(5) . . . . ?
Co1 N3 C18 C17 175.9(3) . . . . ?
C14 N3 C18 C19 -178.6(3) . . . . ?
Co1 N3 C18 C19 -2.6(4) . . . . ?
C11 N2 C10 C9 -0.6(5) . . . . ?
Co1 N2 C10 C9 177.9(3) . . . . ?
N1 C1 C2 C3 1.4(6) . . . . ?
C1 C2 C3 C4 1.0(6) . . . . ?
C12 C4 C3 C2 -2.7(5) . . . . ?
C5 C4 C3 C2 176.9(3) . . . . ?
C11 C7 C8 C9 0.5(5) . . . . ?
C6 C7 C8 C9 -179.8(3) . . . . ?
Co1 O1 C13 C14 -1.1(4) . . . . ?
N3 C14 C13 O1 -1.9(4) . . . . ?
C15 C14 C13 O1 177.5(3) . . . . ?
N3 C14 C15 C16 -1.4(5) . . . . ?
C13 C14 C15 C16 179.2(3) . . . . ?
C7 C8 C9 C10 -1.1(6) . . . . ?
N2 C10 C9 C8 1.1(6) . . . . ?
N3 C18 C17 C16 0.0(6) . . . . ?
C19 C18 C17 C16 178.3(4) . . . . ?
C18 C17 C16 C15 -0.6(6) . . . . ?
C14 C15 C16 C17 1.3(6) . . . . ?
Co1 O2 C19 C18 22.0(4) . . . . ?
N3 C18 C19 O2 -12.7(5) . . . . ?
C17 C18 C19 O2 168.9(3) . . . . ?

_refine_diff_density_max         0.342
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_MF21
_database_code_depnum_ccdc_archive 'CCDC 1842255'
_audit_update_record             
;
2018-05-09 deposited with the CCDC.	2019-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 Co N4 O2 S2'
_chemical_formula_weight         393.34

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

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

_cell_length_a                   11.4021(3)
_cell_length_b                   8.2603(2)
_cell_length_c                   17.7971(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1676.22(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      26.00

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_F_000             804
_exptl_transmission_factor_min   0.730
_exptl_transmission_factor_max   0.825
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.286
_shelx_estimated_absorpt_T_min   0.699
_shelx_estimated_absorpt_T_max   0.831
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER SMART APEX'
_diffrn_measurement_method       /w-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16677
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.045
_diffrn_reflns_theta_max         25.048
_diffrn_reflns_theta_full        25.048
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1477
_reflns_number_gt                1242
_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       'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45 ( Bruker, 2003)'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'DIAMOND 2.1e'
_computing_publication_material  SHELXL
_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)+(0.0274P)²+0.6449P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1477
_refine_ls_number_parameters     108
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0242
_refine_ls_wR_factor_ref         0.0617
_refine_ls_wR_factor_gt          0.0579
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
N1 N 0.35148(14) 0.27464(19) 0.18603(9) 0.0420(4) Uani 1 1 d . . . . .
C5 C 0.36709(17) 0.3577(2) 0.12219(10) 0.0452(5) Uani 1 1 d . . . . .
C1 C 0.24178(19) 0.2341(3) 0.20586(12) 0.0503(5) Uani 1 1 d . . . . .
H1 H 0.230526 0.176514 0.250170 0.060 Uiso 1 1 calc R U . . .
C2 C 0.14540(19) 0.2743(3) 0.16343(13) 0.0593(6) Uani 1 1 d . . . . .
H2 H 0.070424 0.244690 0.178760 0.071 Uiso 1 1 calc R U . . .
C4 C 0.2740(2) 0.4017(3) 0.07703(12) 0.0571(6) Uani 1 1 d . . . . .
H4 H 0.287045 0.459692 0.033019 0.069 Uiso 1 1 calc R U . . .
C3 C 0.1622(2) 0.3595(3) 0.09745(13) 0.0619(6) Uani 1 1 d . . . . .
H3 H 0.098727 0.387756 0.067403 0.074 Uiso 1 1 calc R U . . .
N2 N 0.42186(14) 0.0530(2) 0.32026(10) 0.0504(4) Uani 1 1 d . . . . .
C7 C 0.37715(16) -0.0400(2) 0.35902(10) 0.0403(4) Uani 1 1 d . . . . .
O1 O 0.56093(13) 0.40298(18) 0.16769(8) 0.0513(4) Uani 1 1 d . . . . .
C6 C 0.49138(18) 0.3994(3) 0.10164(12) 0.0537(5) Uani 1 1 d . . . . .
H6A H 0.522117 0.319255 0.066995 0.064 Uiso 1 1 calc R U . . .
H6B H 0.493673 0.504199 0.077115 0.064 Uiso 1 1 calc R U . . .
Co1 Co 0.500000 0.21568(4) 0.250000 0.03840(13) Uani 1 2 d S T P . .
S1 S 0.31572(5) -0.17418(7) 0.41370(3) 0.05871(18) Uani 1 1 d . . . . .
H1A H 0.625(2) 0.386(4) 0.1549(15) 0.088 Uiso 1 1 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
N1 C5 1.339(2) . ?
N1 C1 1.342(3) . ?
N1 Co1 2.0978(16) . ?
C5 C4 1.380(3) . ?
C5 C6 1.504(3) . ?
C1 C2 1.374(3) . ?
C2 C3 1.383(3) . ?
C4 C3 1.370(3) . ?
N2 C7 1.151(2) . ?
N2 Co1 2.0402(18) . ?
C7 S1 1.633(2) . ?
O1 C6 1.418(2) . ?
O1 Co1 2.2410(14) . ?

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
C5 N1 C1 118.34(17) . . ?
C5 N1 Co1 118.17(13) . . ?
C1 N1 Co1 123.49(14) . . ?
N1 C5 C4 121.8(2) . . ?
N1 C5 C6 116.67(17) . . ?
C4 C5 C6 121.53(19) . . ?
N1 C1 C2 122.7(2) . . ?
C1 C2 C3 118.6(2) . . ?
C3 C4 C5 119.6(2) . . ?
C4 C3 C2 119.0(2) . . ?
C7 N2 Co1 179.01(17) . . ?
N2 C7 S1 178.95(18) . . ?
C6 O1 Co1 110.73(12) . . ?
O1 C6 C5 109.28(16) . . ?
N2 Co1 N2 97.62(10) 3_655 . ?
N2 Co1 N1 99.95(6) 3_655 . ?
N2 Co1 N1 97.64(6) . . ?
N2 Co1 N1 97.64(6) 3_655 3_655 ?
N2 Co1 N1 99.95(6) . 3_655 ?
N1 Co1 N1 153.15(9) . 3_655 ?
N2 Co1 O1 85.33(6) 3_655 . ?
N2 Co1 O1 172.15(6) . . ?
N1 Co1 O1 74.65(6) . . ?
N1 Co1 O1 86.80(6) 3_655 . ?
N2 Co1 O1 172.15(6) 3_655 3_655 ?
N2 Co1 O1 85.33(6) . 3_655 ?
N1 Co1 O1 86.80(6) . 3_655 ?
N1 Co1 O1 74.65(6) 3_655 3_655 ?
O1 Co1 O1 92.68(8) . 3_655 ?

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
C1 N1 C5 C4 -0.1(3) . . . . ?
Co1 N1 C5 C4 -179.78(15) . . . . ?
C1 N1 C5 C6 -179.45(18) . . . . ?
Co1 N1 C5 C6 0.8(2) . . . . ?
C5 N1 C1 C2 0.1(3) . . . . ?
Co1 N1 C1 C2 179.75(16) . . . . ?
N1 C1 C2 C3 0.2(3) . . . . ?
N1 C5 C4 C3 -0.2(3) . . . . ?
C6 C5 C4 C3 179.2(2) . . . . ?
C5 C4 C3 C2 0.4(3) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
Co1 O1 C6 C5 34.7(2) . . . . ?
N1 C5 C6 O1 -24.7(3) . . . . ?
C4 C5 C6 O1 155.91(19) . . . . ?

_refine_diff_density_max         0.174
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1842257'
_audit_update_record             
;
2018-05-09 deposited with the CCDC.	2019-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 N4 Ni O2 S2'
_chemical_formula_weight         393.12

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/n'
_space_group_name_Hall           '-P 2yac'

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

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

_cell_length_a                   14.0162(6)
_cell_length_b                   8.1198(4)
_cell_length_c                   14.9569(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.8380(10)
_cell_angle_gamma                90
_cell_volume                     1652.82(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    1.439
_shelx_estimated_absorpt_T_min   0.715
_shelx_estimated_absorpt_T_max   0.824
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19143
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.283
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_full        24.994
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2914
_reflns_number_gt                2522
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0153P)²+1.5055P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2914
_refine_ls_number_parameters     224
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0608
_refine_ls_wR_factor_gt          0.0574
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.132
_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 -0.10139(16) 0.1503(3) 0.39113(16) 0.0221(5) Uani 1 1 d D . . . .
H1A H -0.089243 0.078734 0.446274 0.027 Uiso 1 1 calc R U . . .
H1B H -0.076060 0.261755 0.410615 0.027 Uiso 1 1 calc R U . . .
C2 C -0.04926(16) 0.0823(3) 0.32251(16) 0.0192(5) Uani 1 1 d . . . . .
C3 C 0.05058(16) 0.1046(3) 0.33313(17) 0.0250(6) Uani 1 1 d . . . . .
H3 H 0.087624 0.165279 0.384026 0.030 Uiso 1 1 calc R U . . .
C4 C 0.09585(17) 0.0383(3) 0.26930(18) 0.0284(6) Uani 1 1 d . . . . .
H4 H 0.164354 0.053010 0.275420 0.034 Uiso 1 1 calc R U . . .
C5 C 0.04013(17) -0.0503(3) 0.19598(17) 0.0253(6) Uani 1 1 d . . . . .
H5 H 0.069495 -0.096738 0.150743 0.030 Uiso 1 1 calc R U . . .
C6 C -0.05872(16) -0.0696(3) 0.19019(16) 0.0188(5) Uani 1 1 d . . . . .
H6 H -0.096671 -0.132411 0.140716 0.023 Uiso 1 1 calc R U . . .
C7 C -0.20174(15) -0.2961(3) 0.41091(15) 0.0153(5) Uani 1 1 d . . . . .
C8 C 0.11953(16) 0.3394(3) 0.09589(15) 0.0201(5) Uani 1 1 d D . . . .
H8A H 0.097972 0.227441 0.073725 0.024 Uiso 1 1 calc R U . . .
H8B H 0.113478 0.412027 0.041646 0.024 Uiso 1 1 calc R U . . .
C9 C 0.05588(16) 0.4029(3) 0.15581(15) 0.0175(5) Uani 1 1 d . . . . .
C10 C -0.04450(16) 0.3732(3) 0.13482(17) 0.0233(6) Uani 1 1 d . . . . .
H10 H -0.074479 0.310054 0.082120 0.028 Uiso 1 1 calc R U . . .
C11 C -0.10044(17) 0.4364(3) 0.19132(18) 0.0273(6) Uani 1 1 d . . . . .
H11 H -0.169280 0.417427 0.178015 0.033 Uiso 1 1 calc R U . . .
C12 C -0.05478(17) 0.5276(3) 0.26735(18) 0.0260(6) Uani 1 1 d . . . . .
H12 H -0.091561 0.571949 0.307414 0.031 Uiso 1 1 calc R U . . .
C13 C 0.04530(16) 0.5533(3) 0.28421(16) 0.0194(5) Uani 1 1 d . . . . .
H13 H 0.076373 0.617129 0.336258 0.023 Uiso 1 1 calc R U . . .
C14 C 0.22653(15) 0.7944(3) 0.09423(15) 0.0146(5) Uani 1 1 d . . . . .
N1 N -0.10381(13) -0.0036(2) 0.25122(12) 0.0152(4) Uani 1 1 d . . . . .
N2 N -0.27789(13) -0.1992(2) 0.14684(13) 0.0185(4) Uani 1 1 d . . . . .
N3 N 0.10045(13) 0.4919(2) 0.23027(12) 0.0143(4) Uani 1 1 d . . . . .
N4 N 0.23690(13) 0.6912(2) 0.14895(13) 0.0160(4) Uani 1 1 d . . . . .
O1 O -0.20510(10) 0.1584(2) 0.34987(10) 0.0170(3) Uani 1 1 d D . . . .
O2 O 0.22016(11) 0.33488(19) 0.14782(10) 0.0171(3) Uani 1 1 d D . . . .
Ni1 Ni -0.250000 -0.02977(5) 0.250000 0.01174(11) Uani 1 2 d DS T P . .
Ni2 Ni 0.250000 0.52131(5) 0.250000 0.01127(11) Uani 1 2 d DS T P . .
S1 S -0.17285(16) -0.4384(3) 0.49135(16) 0.0231(3) Uani 0.9 1 d . . P . .
S2 S -0.28974(5) 0.05508(8) 0.51866(4) 0.02222(15) Uani 1 1 d . . . . .
S1A S -0.160(2) -0.420(4) 0.489(2) 0.072(10) Uani 0.1 1 d . . P . .
H1 H -0.2324(14) 0.178(4) 0.3966(13) 0.108 Uiso 1 1 d D U . . .
H2 H 0.2550(13) 0.319(4) 0.1063(14) 0.108 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 O1 1.438(3) . ?
C1 C2 1.500(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N1 1.348(3) . ?
C2 C3 1.382(3) . ?
C3 C4 1.376(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.376(3) . ?
C5 H5 0.9500 . ?
C6 N1 1.340(3) . ?
C6 H6 0.9500 . ?
C7 N2 1.153(3) 2_455 ?
C7 S1A 1.55(3) . ?
C7 S1 1.647(3) . ?
C8 O2 1.439(3) . ?
C8 C9 1.499(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N3 1.349(3) . ?
C9 C10 1.387(3) . ?
C10 C11 1.382(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(3) . ?
C12 H12 0.9500 . ?
C13 N3 1.340(3) . ?
C13 H13 0.9500 . ?
C14 N4 1.156(3) . ?
C14 S2 1.643(2) 4_665 ?
N1 Ni1 2.0558(17) . ?
N2 Ni1 2.034(2) . ?
N3 Ni2 2.0595(17) . ?
N4 Ni2 2.0220(19) . ?
O1 Ni1 2.1243(16) . ?
O1 H1 0.888(9) . ?
O2 Ni2 2.1204(15) . ?
O2 H2 0.887(9) . ?

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 C2 109.33(18) . . ?
O1 C1 H1A 109.8 . . ?
C2 C1 H1A 109.8 . . ?
O1 C1 H1B 109.8 . . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.3 . . ?
N1 C2 C3 121.7(2) . . ?
N1 C2 C1 117.04(19) . . ?
C3 C2 C1 121.2(2) . . ?
C4 C3 C2 119.4(2) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 119.1(2) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 118.5(2) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
N1 C6 C5 122.9(2) . . ?
N1 C6 H6 118.5 . . ?
C5 C6 H6 118.5 . . ?
N2 C7 S1A 172.6(12) 2_455 . ?
N2 C7 S1 178.5(2) 2_455 . ?
S1A C7 S1 7.7(13) . . ?
O2 C8 C9 109.44(18) . . ?
O2 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
O2 C8 H8B 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
N3 C9 C10 121.6(2) . . ?
N3 C9 C8 116.96(19) . . ?
C10 C9 C8 121.4(2) . . ?
C11 C10 C9 119.3(2) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C12 C11 C10 119.0(2) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C13 118.9(2) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
N3 C13 C12 122.8(2) . . ?
N3 C13 H13 118.6 . . ?
C12 C13 H13 118.6 . . ?
N4 C14 S2 178.1(2) . 4_665 ?
C6 N1 C2 118.35(19) . . ?
C6 N1 Ni1 125.74(15) . . ?
C2 N1 Ni1 115.85(15) . . ?
C7 N2 Ni1 176.63(18) 2_455 . ?
C13 N3 C9 118.44(19) . . ?
C13 N3 Ni2 125.78(15) . . ?
C9 N3 Ni2 115.78(14) . . ?
C14 N4 Ni2 175.85(18) . . ?
C1 O1 Ni1 111.58(13) . . ?
C1 O1 H1 104.6(15) . . ?
Ni1 O1 H1 124.9(16) . . ?
C8 O2 Ni2 111.69(13) . . ?
C8 O2 H2 105.0(15) . . ?
Ni2 O2 H2 124.1(16) . . ?
N2 Ni1 N2 94.88(11) . 2_455 ?
N2 Ni1 N1 94.99(7) . . ?
N2 Ni1 N1 93.03(7) 2_455 . ?
N2 Ni1 N1 93.03(7) . 2_455 ?
N2 Ni1 N1 94.99(7) 2_455 2_455 ?
N1 Ni1 N1 168.14(10) . 2_455 ?
N2 Ni1 O1 172.20(7) . . ?
N2 Ni1 O1 88.98(7) 2_455 . ?
N1 Ni1 O1 78.02(6) . . ?
N1 Ni1 O1 93.38(6) 2_455 . ?
N2 Ni1 O1 88.98(7) . 2_455 ?
N2 Ni1 O1 172.20(7) 2_455 2_455 ?
N1 Ni1 O1 93.38(6) . 2_455 ?
N1 Ni1 O1 78.02(6) 2_455 2_455 ?
O1 Ni1 O1 88.00(9) . 2_455 ?
N4 Ni2 N4 93.95(11) 2 . ?
N4 Ni2 N3 95.37(7) 2 . ?
N4 Ni2 N3 93.70(7) . . ?
N4 Ni2 N3 93.70(7) 2 2 ?
N4 Ni2 N3 95.37(7) . 2 ?
N3 Ni2 N3 166.69(10) . 2 ?
N4 Ni2 O2 88.94(7) 2 2 ?
N4 Ni2 O2 173.12(6) . 2 ?
N3 Ni2 O2 92.24(6) . 2 ?
N3 Ni2 O2 78.20(6) 2 2 ?
N4 Ni2 O2 173.12(6) 2 . ?
N4 Ni2 O2 88.94(7) . . ?
N3 Ni2 O2 78.20(6) . . ?
N3 Ni2 O2 92.24(6) 2 . ?
O2 Ni2 O2 88.89(9) 2 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 N1 -20.0(3) . . . . ?
O1 C1 C2 C3 161.1(2) . . . . ?
N1 C2 C3 C4 0.2(4) . . . . ?
C1 C2 C3 C4 179.1(2) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 -0.5(4) . . . . ?
C4 C5 C6 N1 1.4(4) . . . . ?
O2 C8 C9 N3 21.2(3) . . . . ?
O2 C8 C9 C10 -159.6(2) . . . . ?
N3 C9 C10 C11 0.1(4) . . . . ?
C8 C9 C10 C11 -179.0(2) . . . . ?
C9 C10 C11 C12 0.0(4) . . . . ?
C10 C11 C12 C13 0.3(4) . . . . ?
C11 C12 C13 N3 -0.7(4) . . . . ?
C5 C6 N1 C2 -1.5(3) . . . . ?
C5 C6 N1 Ni1 -178.54(17) . . . . ?
C3 C2 N1 C6 0.7(3) . . . . ?
C1 C2 N1 C6 -178.2(2) . . . . ?
C3 C2 N1 Ni1 177.98(18) . . . . ?
C1 C2 N1 Ni1 -0.9(3) . . . . ?
C12 C13 N3 C9 0.8(3) . . . . ?
C12 C13 N3 Ni2 -179.44(17) . . . . ?
C10 C9 N3 C13 -0.5(3) . . . . ?
C8 C9 N3 C13 178.7(2) . . . . ?
C10 C9 N3 Ni2 179.70(17) . . . . ?
C8 C9 N3 Ni2 -1.1(3) . . . . ?
C2 C1 O1 Ni1 30.4(2) . . . . ?
C9 C8 O2 Ni2 -30.3(2) . . . . ?

_refine_diff_density_max         0.403
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_Complex2
_database_code_depnum_ccdc_archive 'CCDC 1525979'
_audit_update_record             
;
2018-05-09 deposited with the CCDC.	2019-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 Cl2 Mn N3 O2'
_chemical_formula_weight         445.19

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'
Cl Cl 0.1484 0.1585 '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'

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

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

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

_cell_length_a                   11.345(3)
_cell_length_b                   13.870(4)
_cell_length_c                   12.108(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.824(7)
_cell_angle_gamma                90
_cell_volume                     1857.8(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      26.00

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_F_000             908
_exptl_transmission_factor_min   0.783
_exptl_transmission_factor_max   0.850
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    1.018
_shelx_estimated_absorpt_T_min   0.750
_shelx_estimated_absorpt_T_max   0.854
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER SMART APEX'
_diffrn_measurement_method       /w-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20988
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.667
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_full        25.047
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3291
_reflns_number_gt                2711
_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       'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45 ( Bruker, 2003)'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'DIAMOND 2.1e'
_computing_publication_material  SHELXL

_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)+(0.0354P)²+1.0679P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3291
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0796
_refine_ls_wR_factor_gt          0.0737
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
Mn1 Mn 0.32169(3) 0.73892(2) 0.70051(3) 0.02835(12) Uani 1 1 d . . . . .
Cl1 Cl 0.38703(6) 0.86300(5) 0.84044(6) 0.04403(18) Uani 1 1 d . . . . .
Cl2 Cl 0.66583(6) 0.60103(6) 0.89781(6) 0.0574(2) Uani 1 1 d . . . . .
O1 O 0.14808(15) 0.81092(13) 0.61950(15) 0.0381(4) Uani 1 1 d . . . . .
N3 N 0.17165(17) 0.66398(13) 0.75635(15) 0.0277(4) Uani 1 1 d . . . . .
O2 O 0.39766(17) 0.61756(15) 0.80945(18) 0.0511(5) Uani 1 1 d . . . . .
N1 N 0.28867(17) 0.63967(14) 0.54463(16) 0.0311(4) Uani 1 1 d . . . . .
N2 N 0.48460(17) 0.75017(13) 0.62468(16) 0.0310(5) Uani 1 1 d . . . . .
C12 C 0.3828(2) 0.63233(16) 0.49286(18) 0.0261(5) Uani 1 1 d . . . . .
C11 C 0.4880(2) 0.69020(16) 0.53697(18) 0.0257(5) Uani 1 1 d . . . . .
C7 C 0.5895(2) 0.68191(16) 0.48896(19) 0.0296(5) Uani 1 1 d . . . . .
C4 C 0.3819(2) 0.57051(16) 0.40134(19) 0.0301(5) Uani 1 1 d . . . . .
C14 C 0.0582(2) 0.69640(17) 0.72276(19) 0.0306(5) Uani 1 1 d . . . . .
C18 C 0.1971(2) 0.59307(17) 0.8325(2) 0.0341(6) Uani 1 1 d . . . . .
C5 C 0.4871(2) 0.56425(18) 0.3548(2) 0.0368(6) Uani 1 1 d . . . . .
H5 H 0.486776 0.522972 0.294244 0.044 Uiso 1 1 calc R U . . .
C6 C 0.5863(2) 0.61675(17) 0.3969(2) 0.0359(6) Uani 1 1 d . . . . .
H6 H 0.653878 0.610637 0.365729 0.043 Uiso 1 1 calc R U . . .
C8 C 0.6899(2) 0.73980(18) 0.5351(2) 0.0384(6) Uani 1 1 d . . . . .
H8 H 0.759186 0.736670 0.506145 0.046 Uiso 1 1 calc R U . . .
C1 C 0.1924(2) 0.58543(18) 0.5054(2) 0.0377(6) Uani 1 1 d . . . . .
H1A H 0.127864 0.589134 0.541006 0.045 Uiso 1 1 calc R U . . .
C3 C 0.2771(2) 0.51562(18) 0.3620(2) 0.0368(6) Uani 1 1 d . . . . .
H3 H 0.272228 0.474216 0.300745 0.044 Uiso 1 1 calc R U . . .
C13 C 0.0366(2) 0.77046(18) 0.6306(2) 0.0368(6) Uani 1 1 d . . . . .
H13A H -0.003517 0.740820 0.559629 0.044 Uiso 1 1 calc R U . . .
H13B H -0.015575 0.820847 0.648304 0.044 Uiso 1 1 calc R U . . .
C2 C 0.1830(2) 0.52321(19) 0.4138(2) 0.0402(6) Uani 1 1 d . . . . .
H2A H 0.113044 0.487248 0.388350 0.048 Uiso 1 1 calc R U . . .
C9 C 0.6853(2) 0.8004(2) 0.6221(2) 0.0435(7) Uani 1 1 d . . . . .
H9 H 0.750868 0.839722 0.652563 0.052 Uiso 1 1 calc R U . . .
C10 C 0.5814(2) 0.80322(19) 0.6654(2) 0.0391(6) Uani 1 1 d . . . . .
H10 H 0.579939 0.844338 0.725721 0.047 Uiso 1 1 calc R U . . .
C15 C -0.0334(2) 0.66047(19) 0.7702(2) 0.0410(6) Uani 1 1 d . . . . .
H15 H -0.111341 0.685264 0.749176 0.049 Uiso 1 1 calc R U . . .
C16 C -0.0071(2) 0.5876(2) 0.8486(2) 0.0472(7) Uani 1 1 d . . . . .
H16 H -0.067603 0.562476 0.880898 0.057 Uiso 1 1 calc R U . . .
C17 C 0.1083(3) 0.55203(19) 0.8793(2) 0.0448(7) Uani 1 1 d . . . . .
H17 H 0.126479 0.501329 0.930539 0.054 Uiso 1 1 calc R U . . .
C19 C 0.3259(2) 0.5597(2) 0.8632(3) 0.0484(7) Uani 1 1 d . . . . .
H19A H 0.355659 0.563269 0.944641 0.058 Uiso 1 1 calc R U . . .
H19B H 0.330696 0.493122 0.840160 0.058 Uiso 1 1 calc R U . . .
H1 H 0.144(3) 0.833(2) 0.559(3) 0.073 Uiso 1 1 d . U . . .
H2 H 0.466(3) 0.614(2) 0.836(3) 0.073 Uiso 1 1 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
Mn1 O2 2.1936(19) . ?
Mn1 N3 2.2238(19) . ?
Mn1 O1 2.2318(18) . ?
Mn1 N2 2.2443(19) . ?
Mn1 N1 2.2987(19) . ?
Mn1 Cl1 2.4134(8) . ?
O1 C13 1.417(3) . ?
O1 H1 0.79(3) . ?
N3 C18 1.335(3) . ?
N3 C14 1.339(3) . ?
O2 C19 1.402(3) . ?
O2 H2 0.77(3) . ?
N1 C1 1.324(3) . ?
N1 C12 1.357(3) . ?
N2 C10 1.323(3) . ?
N2 C11 1.356(3) . ?
C12 C4 1.399(3) . ?
C12 C11 1.439(3) . ?
C11 C7 1.406(3) . ?
C7 C8 1.403(3) . ?
C7 C6 1.429(3) . ?
C4 C3 1.403(3) . ?
C4 C5 1.431(3) . ?
C14 C15 1.386(3) . ?
C14 C13 1.496(3) . ?
C18 C17 1.383(3) . ?
C18 C19 1.499(4) . ?
C5 C6 1.342(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 C9 1.359(4) . ?
C8 H8 0.9300 . ?
C1 C2 1.391(3) . ?
C1 H1A 0.9300 . ?
C3 C2 1.358(4) . ?
C3 H3 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C2 H2A 0.9300 . ?
C9 C10 1.392(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C15 C16 1.373(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.371(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 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
O2 Mn1 N3 71.55(7) . . ?
O2 Mn1 O1 142.97(7) . . ?
N3 Mn1 O1 71.48(7) . . ?
O2 Mn1 N2 92.87(7) . . ?
N3 Mn1 N2 155.82(7) . . ?
O1 Mn1 N2 121.04(7) . . ?
O2 Mn1 N1 90.28(8) . . ?
N3 Mn1 N1 88.48(7) . . ?
O1 Mn1 N1 86.56(7) . . ?
N2 Mn1 N1 72.82(7) . . ?
O2 Mn1 Cl1 96.12(7) . . ?
N3 Mn1 Cl1 104.86(5) . . ?
O1 Mn1 Cl1 95.34(5) . . ?
N2 Mn1 Cl1 94.88(5) . . ?
N1 Mn1 Cl1 166.45(5) . . ?
C13 O1 Mn1 120.02(14) . . ?
C13 O1 H1 112(3) . . ?
Mn1 O1 H1 117(3) . . ?
C18 N3 C14 120.2(2) . . ?
C18 N3 Mn1 119.46(15) . . ?
C14 N3 Mn1 120.00(15) . . ?
C19 O2 Mn1 121.82(15) . . ?
C19 O2 H2 114(3) . . ?
Mn1 O2 H2 121(3) . . ?
C1 N1 C12 117.6(2) . . ?
C1 N1 Mn1 127.28(16) . . ?
C12 N1 Mn1 115.00(14) . . ?
C10 N2 C11 117.9(2) . . ?
C10 N2 Mn1 125.25(16) . . ?
C11 N2 Mn1 116.54(14) . . ?
N1 C12 C4 122.9(2) . . ?
N1 C12 C11 117.36(19) . . ?
C4 C12 C11 119.7(2) . . ?
N2 C11 C7 122.8(2) . . ?
N2 C11 C12 117.87(19) . . ?
C7 C11 C12 119.3(2) . . ?
C8 C7 C11 117.1(2) . . ?
C8 C7 C6 123.4(2) . . ?
C11 C7 C6 119.5(2) . . ?
C12 C4 C3 117.3(2) . . ?
C12 C4 C5 119.2(2) . . ?
C3 C4 C5 123.5(2) . . ?
N3 C14 C15 120.8(2) . . ?
N3 C14 C13 116.4(2) . . ?
C15 C14 C13 122.8(2) . . ?
N3 C18 C17 121.4(2) . . ?
N3 C18 C19 116.6(2) . . ?
C17 C18 C19 122.0(2) . . ?
C6 C5 C4 121.4(2) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 120.9(2) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C9 C8 C7 119.7(2) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
N1 C1 C2 123.4(2) . . ?
N1 C1 H1A 118.3 . . ?
C2 C1 H1A 118.3 . . ?
C2 C3 C4 119.7(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
O1 C13 C14 109.93(19) . . ?
O1 C13 H13A 109.7 . . ?
C14 C13 H13A 109.7 . . ?
O1 C13 H13B 109.7 . . ?
C14 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C3 C2 C1 119.2(2) . . ?
C3 C2 H2A 120.4 . . ?
C1 C2 H2A 120.4 . . ?
C8 C9 C10 119.4(2) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
N2 C10 C9 123.1(2) . . ?
N2 C10 H10 118.4 . . ?
C9 C10 H10 118.4 . . ?
C16 C15 C14 118.9(2) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C17 C16 C15 120.0(2) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 118.6(3) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
O2 C19 C18 110.1(2) . . ?
O2 C19 H19A 109.6 . . ?
C18 C19 H19A 109.6 . . ?
O2 C19 H19B 109.6 . . ?
C18 C19 H19B 109.6 . . ?
H19A C19 H19B 108.2 . . ?

_refine_diff_density_max         0.256
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.053

