# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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 1811943'
_audit_update_record             
;
2018-01-23 deposited with the CCDC.
2018-01-26 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            'C36 H36 Cl4 Cu2 Mn2 N4 O4'
_chemical_formula_weight         967.45

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.946(3)
_cell_length_b                   11.530(7)
_cell_length_c                   11.732(4)
_cell_angle_alpha                108.443(6)
_cell_angle_beta                 113.238(4)
_cell_angle_gamma                96.187(6)
_cell_volume                     1130.1(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    360
_cell_measurement_theta_min      1.932
_cell_measurement_theta_max      25.150

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    1.748
_exptl_absorpt_correction_type   EMPIRICAL
_exptl_absorpt_correction_T_min  0.920
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_process_details   SADABS

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7720
_diffrn_reflns_av_unetI/netI     0.0900
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.932
_diffrn_reflns_theta_max         25.150
_diffrn_reflns_theta_full        25.150
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             3916
_reflns_number_gt                2328
_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.
 
 Structure factors included contributions from the .fab file.
 Squeeze calculations postulated the presence of electron density 
 equivalent to three methanol solvent molecules in the unitcell
 
 _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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_publication_material  'SHELXL-2016/6, PLATON, WINGX (Ferrugia, 2012)'

_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)+(0.0556P)²] 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         3916
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1210
_refine_ls_wR_factor_gt          0.1035
_refine_ls_goodness_of_fit_ref   0.931
_refine_ls_restrained_S_all      0.931
_refine_ls_shift/su_max          0.002
_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
Cu1 Cu 0.02734(6) 0.03190(6) 0.27266(6) 0.0433(2) Uani 1 1 d . . . . .
Mn1 Mn 0.38508(8) 0.06028(7) 0.37723(7) 0.0394(2) Uani 1 1 d . . . . .
Cl1 Cl 0.50000(14) 0.17042(13) 0.28711(13) 0.0522(4) Uani 1 1 d . . . . .
Cl2 Cl 0.43436(14) -0.14403(13) 0.37468(12) 0.0493(4) Uani 1 1 d . . . . .
O2 O 0.1609(3) -0.0359(3) 0.2023(3) 0.0435(9) Uani 1 1 d . . . . .
O1 O 0.2188(3) 0.1416(3) 0.4181(3) 0.0415(9) Uani 1 1 d . . . . .
N1 N -0.0719(4) 0.0896(4) 0.3907(4) 0.0462(11) Uani 1 1 d . . . . .
N2 N -0.1522(4) -0.0768(4) 0.1105(4) 0.0487(11) Uani 1 1 d . . . . .
C1 C 0.2297(6) 0.2622(5) 0.4874(5) 0.0438(13) Uani 1 1 d . . . . .
C2 C 0.3536(6) 0.3578(5) 0.5252(5) 0.0533(15) Uani 1 1 d . . . . .
H2 H 0.432049 0.336745 0.505769 0.064 Uiso 1 1 calc R U . . .
C3 C 0.3649(7) 0.4820(6) 0.5900(5) 0.0660(17) Uani 1 1 d . . . . .
H3 H 0.449670 0.544287 0.613360 0.079 Uiso 1 1 calc R U . . .
C4 C 0.2507(7) 0.5157(6) 0.6213(6) 0.0704(18) Uani 1 1 d . . . . .
H4 H 0.255419 0.600592 0.662118 0.085 Uiso 1 1 calc R U . . .
C5 C 0.1305(7) 0.4215(6) 0.5908(6) 0.0695(18) Uani 1 1 d . . . . .
H5 H 0.056460 0.443660 0.616440 0.083 Uiso 1 1 calc R U . . .
C6 C 0.1148(6) 0.2925(5) 0.5221(5) 0.0473(14) Uani 1 1 d . . . . .
C7 C -0.0197(6) 0.1981(6) 0.4903(5) 0.0526(15) Uani 1 1 d . . . . .
C8 C -0.0931(6) 0.2335(7) 0.5838(6) 0.082(2) Uani 1 1 d . . . . .
H8A H -0.187808 0.250409 0.537847 0.123 Uiso 1 1 calc R U . . .
H8B H -0.026728 0.307859 0.662779 0.123 Uiso 1 1 calc R U . . .
H8C H -0.110976 0.164606 0.609806 0.123 Uiso 1 1 calc R U . . .
C9 C -0.2105(6) 0.0012(6) 0.3663(6) 0.0622(17) Uani 1 1 d . . . . .
H9A H -0.286874 0.047176 0.365285 0.075 Uiso 1 1 calc R U . . .
H9B H -0.185395 -0.024947 0.441406 0.075 Uiso 1 1 calc R U . . .
C10 C -0.2784(6) -0.1155(6) 0.2379(6) 0.0699(19) Uani 1 1 d . . . . .
H10A H -0.376545 -0.158867 0.223282 0.084 Uiso 1 1 calc R U . . .
H10B H -0.213461 -0.172423 0.247242 0.084 Uiso 1 1 calc R U . . .
C11 C -0.2981(6) -0.0864(6) 0.1165(6) 0.0669(18) Uani 1 1 d . . . . .
H11A H -0.377667 -0.153371 0.034941 0.080 Uiso 1 1 calc R U . . .
H11B H -0.325979 -0.007136 0.124736 0.080 Uiso 1 1 calc R U . . .
C12 C -0.1517(6) -0.1458(5) 0.0016(5) 0.0506(14) Uani 1 1 d . . . . .
H12 H -0.246850 -0.190804 -0.070377 0.061 Uiso 1 1 calc R U . . .
C13 C -0.0254(6) -0.1638(5) -0.0255(5) 0.0477(14) Uani 1 1 d . . . . .
C14 C -0.0534(7) -0.2386(5) -0.1560(5) 0.0604(16) Uani 1 1 d . . . . .
H14 H -0.153261 -0.271080 -0.223446 0.072 Uiso 1 1 calc R U . . .
C15 C 0.0591(7) -0.2660(6) -0.1884(5) 0.0648(17) Uani 1 1 d . . . . .
H15 H 0.037631 -0.317274 -0.275942 0.078 Uiso 1 1 calc R U . . .
C16 C 0.2090(7) -0.2145(6) -0.0860(6) 0.0655(17) Uani 1 1 d . . . . .
H16 H 0.288086 -0.232866 -0.105702 0.079 Uiso 1 1 calc R U . . .
C17 C 0.2410(6) -0.1383(5) 0.0417(5) 0.0535(15) Uani 1 1 d . . . . .
H17 H 0.341723 -0.104227 0.107101 0.064 Uiso 1 1 calc R U . . .
C18 C 0.1266(6) -0.1100(5) 0.0770(5) 0.0421(13) 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
Cu1 O1 1.921(3) . ?
Cu1 O2 1.933(3) . ?
Cu1 N2 1.925(4) . ?
Cu1 N1 1.993(4) . ?
Mn1 O1 2.125(3) . ?
Mn1 O2 2.198(3) . ?
Mn1 Cl1 2.3510(16) . ?
Mn1 Cl2 2.451(2) . ?
Mn1 Cl2 2.5203(16) 2_656 ?
O2 C18 1.324(5) . ?
O1 C1 1.338(6) . ?
N1 C7 1.287(7) . ?
N1 C9 1.490(6) . ?
N2 C12 1.275(6) . ?
N2 C11 1.475(6) . ?
C1 C2 1.377(7) . ?
C1 C6 1.399(6) . ?
C2 C3 1.360(7) . ?
C3 C4 1.382(7) . ?
C4 C5 1.369(8) . ?
C5 C6 1.406(7) . ?
C6 C7 1.466(7) . ?
C7 C8 1.522(7) . ?
C9 C10 1.502(7) . ?
C10 C11 1.509(7) . ?
C12 C13 1.432(7) . ?
C13 C14 1.394(7) . ?
C13 C18 1.417(6) . ?
C14 C15 1.354(7) . ?
C15 C16 1.401(7) . ?
C16 C17 1.360(7) . ?
C17 C18 1.392(7) . ?

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 Cu1 O2 80.86(13) . . ?
O1 Cu1 N2 171.99(16) . . ?
O2 Cu1 N2 92.68(16) . . ?
O1 Cu1 N1 89.50(15) . . ?
O2 Cu1 N1 162.96(14) . . ?
N2 Cu1 N1 97.90(18) . . ?
O1 Mn1 O2 70.62(12) . . ?
O1 Mn1 Cl1 112.11(11) . . ?
O2 Mn1 Cl1 99.99(10) . . ?
O1 Mn1 Cl2 128.58(10) . . ?
O2 Mn1 Cl2 91.01(10) . . ?
Cl1 Mn1 Cl2 118.33(6) . . ?
O1 Mn1 Cl2 91.37(9) . 2_656 ?
O2 Mn1 Cl2 153.09(9) . 2_656 ?
Cl1 Mn1 Cl2 105.39(6) . 2_656 ?
Cl2 Mn1 Cl2 84.80(5) . 2_656 ?
Mn1 Cl2 Mn1 95.20(5) . 2_656 ?
C18 O2 Cu1 128.5(3) . . ?
C18 O2 Mn1 129.2(3) . . ?
Cu1 O2 Mn1 101.91(14) . . ?
C1 O1 Cu1 120.2(3) . . ?
C1 O1 Mn1 129.5(3) . . ?
Cu1 O1 Mn1 105.01(14) . . ?
C7 N1 C9 117.9(5) . . ?
C7 N1 Cu1 123.4(4) . . ?
C9 N1 Cu1 118.7(4) . . ?
C12 N2 C11 118.3(4) . . ?
C12 N2 Cu1 124.3(4) . . ?
C11 N2 Cu1 117.3(3) . . ?
O1 C1 C2 120.5(5) . . ?
O1 C1 C6 120.2(5) . . ?
C2 C1 C6 119.3(5) . . ?
C3 C2 C1 122.1(5) . . ?
C2 C3 C4 120.2(6) . . ?
C5 C4 C3 118.5(6) . . ?
C4 C5 C6 122.5(5) . . ?
C1 C6 C5 117.4(5) . . ?
C1 C6 C7 123.8(5) . . ?
C5 C6 C7 118.9(5) . . ?
N1 C7 C6 122.3(5) . . ?
N1 C7 C8 121.2(5) . . ?
C6 C7 C8 116.4(5) . . ?
N1 C9 C10 115.3(4) . . ?
C9 C10 C11 112.9(5) . . ?
N2 C11 C10 107.5(4) . . ?
N2 C12 C13 129.2(5) . . ?
C14 C13 C18 119.2(5) . . ?
C14 C13 C12 118.9(5) . . ?
C18 C13 C12 121.9(5) . . ?
C15 C14 C13 122.6(5) . . ?
C14 C15 C16 117.9(5) . . ?
C17 C16 C15 121.2(6) . . ?
C16 C17 C18 121.6(5) . . ?
O2 C18 C17 120.4(4) . . ?
O2 C18 C13 122.1(5) . . ?
C17 C18 C13 117.5(5) . . ?

_refine_diff_density_max         0.494
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.083


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

data_2
_database_code_depnum_ccdc_archive 'CCDC 1811944'
_audit_update_record             
;
2018-01-23 deposited with the CCDC.
2018-01-26 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         'C40 H42 Cl2 Cu2 Mn N6 O4,2(C2 H3 N)'
_chemical_formula_sum            'C44 H48 Cl2 Cu2 Mn N8 O4'
_chemical_formula_weight         1005.84
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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   27.370(5)
_cell_length_b                   10.066(5)
_cell_length_c                   19.407(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 118.944(5)
_cell_angle_gamma                90.00
_cell_volume                     4679(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    14988
_cell_measurement_theta_min      1.700
_cell_measurement_theta_max      24.789

_exptl_crystal_description       Prisamatic
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_F_000             2068
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    1.330
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   EMPIRICAL
_exptl_absorpt_correction_T_min  0.923
_exptl_absorpt_correction_T_max  0.961

_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14988
_diffrn_reflns_av_unetI/netI     0.0765
_diffrn_reflns_av_R_equivalents  0.0821
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.700
_diffrn_reflns_theta_max         24.789
_diffrn_reflns_theta_full        24.789
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             4023
_reflns_number_gt                2754
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0542P)²] 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         3977
_refine_ls_number_parameters     279
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1283
_refine_ls_wR_factor_gt          0.1132
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
Cu1 Cu 0.43194(2) 0.17605(5) 0.65204(3) 0.0443(2) Uani 1 1 d . . . . .
Mn1 Mn 0.5000 0.43630(9) 0.7500 0.0437(3) Uani 1 2 d S T P . .
Cl1 Cl 0.47653(5) 0.59774(12) 0.82422(8) 0.0626(4) Uani 1 1 d . . . . .
O1 O 0.41863(10) 0.3584(3) 0.66730(17) 0.0479(7) Uani 1 1 d . . . . .
O2 O 0.50469(11) 0.2457(3) 0.67741(18) 0.0531(8) Uani 1 1 d . . . . .
N2 N 0.44925(13) 0.0033(3) 0.6230(2) 0.0509(9) Uani 1 1 d . . . . .
N1 N 0.36216(13) 0.1218(3) 0.6531(2) 0.0456(9) Uani 1 1 d . . . . .
C13 C 0.53316(17) 0.0743(5) 0.6181(3) 0.0532(12) Uani 1 1 d . . . . .
C6 C 0.31903(16) 0.3385(4) 0.6091(3) 0.0460(11) Uani 1 1 d . . . . .
C1 C 0.36772(15) 0.4121(4) 0.6256(2) 0.0443(11) Uani 1 1 d . . . . .
C2 C 0.36296(18) 0.5430(4) 0.6008(3) 0.0593(13) Uani 1 1 d . . . . .
H2 H 0.3950 0.5919 0.6131 0.071 Uiso 1 1 calc R U . . .
C5 C 0.26675(17) 0.4039(5) 0.5649(3) 0.0657(15) Uani 1 1 d . . . . .
H5 H 0.2342 0.3579 0.5532 0.079 Uiso 1 1 calc R U . . .
C7 C 0.32054(16) 0.2014(4) 0.6365(3) 0.0490(12) Uani 1 1 d . . . . .
C18 C 0.53890(16) 0.2004(4) 0.6520(3) 0.0489(11) Uani 1 1 d . . . . .
C9 C 0.35870(18) -0.0148(5) 0.6808(3) 0.0591(13) Uani 1 1 d . . . . .
H9A H 0.3230 -0.0534 0.6441 0.071 Uiso 1 1 calc R U . . .
H9B H 0.3600 -0.0078 0.7315 0.071 Uiso 1 1 calc R U . . .
C17 C 0.58386(17) 0.2812(5) 0.6613(3) 0.0592(13) Uani 1 1 d . . . . .
H17 H 0.5885 0.3653 0.6836 0.071 Uiso 1 1 calc R U . . .
C8 C 0.2719(2) 0.1581(5) 0.6480(4) 0.0758(16) Uani 1 1 d . . . . .
H8A H 0.2474 0.1023 0.6050 0.114 Uiso 1 1 calc R U . . .
H8B H 0.2518 0.2350 0.6500 0.114 Uiso 1 1 calc R U . . .
H8C H 0.2857 0.1096 0.6965 0.114 Uiso 1 1 calc R U . . .
C11 C 0.41337(19) -0.1100(5) 0.6176(3) 0.0664(15) Uani 1 1 d . . . . .
H11A H 0.4310 -0.1928 0.6162 0.080 Uiso 1 1 calc R U . . .
H11B H 0.3777 -0.1035 0.5698 0.080 Uiso 1 1 calc R U . . .
C12 C 0.49029(17) -0.0191(5) 0.6098(3) 0.0559(12) Uani 1 1 d . . . . .
H12 H 0.4927 -0.1043 0.5932 0.067 Uiso 1 1 calc R U . . .
C14 C 0.5722(2) 0.0325(6) 0.5949(3) 0.0740(16) Uani 1 1 d . . . . .
H14 H 0.5683 -0.0511 0.5724 0.089 Uiso 1 1 calc R U . . .
C3 C 0.3109(2) 0.6016(5) 0.5576(3) 0.0789(17) Uani 1 1 d . . . . .
H3 H 0.3084 0.6891 0.5408 0.095 Uiso 1 1 calc R U . . .
C10 C 0.40462(19) -0.1074(4) 0.6887(3) 0.0644(14) Uani 1 1 d . . . . .
H10A H 0.4393 -0.0810 0.7343 0.077 Uiso 1 1 calc R U . . .
H10B H 0.3959 -0.1966 0.6982 0.077 Uiso 1 1 calc R U . . .
C16 C 0.6210(2) 0.2362(6) 0.6376(3) 0.0730(15) Uani 1 1 d . . . . .
H16 H 0.6502 0.2909 0.6439 0.088 Uiso 1 1 calc R U . . .
N5 N 0.3737(2) 0.2229(5) 0.4807(3) 0.0918(16) Uani 1 1 d . . . . .
C4 C 0.26281(19) 0.5319(5) 0.5393(3) 0.0805(18) Uani 1 1 d . . . . .
H4 H 0.2280 0.5715 0.5097 0.097 Uiso 1 1 calc R U . . .
C21 C 0.4006(2) 0.3088(6) 0.4830(3) 0.0713(16) Uani 1 1 d . . . . .
C15 C 0.6157(2) 0.1116(6) 0.6045(4) 0.0834(18) Uani 1 1 d . . . . .
H15 H 0.6413 0.0823 0.5892 0.100 Uiso 1 1 calc R U . . .
C23 C 0.2860(3) 0.2817(8) 0.2243(5) 0.105(2) Uani 1 1 d . . . . .
C24 C 0.3180(3) 0.4018(7) 0.2582(4) 0.110(2) Uani 1 1 d . . . . .
H24A H 0.3535 0.3947 0.2599 0.165 Uiso 1 1 calc R U . . .
H24B H 0.3237 0.4134 0.3107 0.165 Uiso 1 1 calc R U . . .
H24C H 0.2981 0.4769 0.2266 0.165 Uiso 1 1 calc R U . . .
N6 N 0.2613(3) 0.1907(7) 0.1975(6) 0.171(4) Uani 1 1 d . . . . .
C22 C 0.4361(3) 0.4180(7) 0.4882(4) 0.116(2) Uani 1 1 d . . . . .
H22A H 0.4142 0.4978 0.4703 0.174 Uiso 1 1 calc R U . . .
H22B H 0.4529 0.4002 0.4558 0.174 Uiso 1 1 calc R U . . .
H22C H 0.4647 0.4291 0.5418 0.174 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.922(3) . ?
Cu1 O2 1.936(3) . ?
Cu1 N2 1.955(4) . ?
Cu1 N1 1.996(3) . ?
Mn1 O1 2.166(3) 2_656 ?
Mn1 O1 2.166(3) . ?
Mn1 O2 2.420(3) . ?
Mn1 O2 2.420(3) 2_656 ?
Mn1 Cl1 2.4543(15) . ?
Mn1 Cl1 2.4543(15) 2_656 ?
O1 C1 1.340(4) . ?
O2 C18 1.332(5) . ?
N2 C12 1.287(5) . ?
N2 C11 1.476(5) . ?
N1 C7 1.300(5) . ?
N1 C9 1.496(5) . ?
C13 C18 1.403(6) . ?
C13 C14 1.410(6) . ?
C13 C12 1.450(6) . ?
C6 C1 1.419(5) . ?
C6 C5 1.424(6) . ?
C6 C7 1.472(6) . ?
C1 C2 1.388(6) . ?
C2 C3 1.388(6) . ?
C5 C4 1.367(7) . ?
C7 C8 1.517(6) . ?
C18 C17 1.412(6) . ?
C9 C10 1.512(6) . ?
C17 C16 1.379(6) . ?
C11 C10 1.510(7) . ?
C14 C15 1.368(7) . ?
C3 C4 1.377(7) . ?
C16 C15 1.384(7) . ?
N5 C21 1.123(7) . ?
C21 C22 1.437(8) . ?
C23 N6 1.108(8) . ?
C23 C24 1.451(10) . ?

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 Cu1 O2 82.15(11) . . ?
O1 Cu1 N2 169.72(15) . . ?
O2 Cu1 N2 91.84(13) . . ?
O1 Cu1 N1 90.36(13) . . ?
O2 Cu1 N1 165.42(14) . . ?
N2 Cu1 N1 97.25(15) . . ?
O1 Mn1 O1 137.56(15) 2_656 . ?
O1 Mn1 O2 79.58(11) 2_656 . ?
O1 Mn1 O2 66.85(10) . . ?
O1 Mn1 O2 66.85(10) 2_656 2_656 ?
O1 Mn1 O2 79.58(11) . 2_656 ?
O2 Mn1 O2 75.10(15) . 2_656 ?
O1 Mn1 Cl1 105.79(8) 2_656 . ?
O1 Mn1 Cl1 101.96(8) . . ?
O2 Mn1 Cl1 165.74(7) . . ?
O2 Mn1 Cl1 94.63(8) 2_656 . ?
O1 Mn1 Cl1 101.96(8) 2_656 2_656 ?
O1 Mn1 Cl1 105.79(8) . 2_656 ?
O2 Mn1 Cl1 94.63(8) . 2_656 ?
O2 Mn1 Cl1 165.74(7) 2_656 2_656 ?
Cl1 Mn1 Cl1 97.07(7) . 2_656 ?
C1 O1 Cu1 120.7(2) . . ?
C1 O1 Mn1 134.2(3) . . ?
Cu1 O1 Mn1 104.85(11) . . ?
C18 O2 Cu1 127.0(3) . . ?
C18 O2 Mn1 137.0(3) . . ?
Cu1 O2 Mn1 95.58(11) . . ?
C12 N2 C11 117.7(4) . . ?
C12 N2 Cu1 124.7(3) . . ?
C11 N2 Cu1 117.5(3) . . ?
C7 N1 C9 117.1(4) . . ?
C7 N1 Cu1 123.9(3) . . ?
C9 N1 Cu1 118.9(3) . . ?
C18 C13 C14 119.3(4) . . ?
C18 C13 C12 122.6(4) . . ?
C14 C13 C12 118.0(4) . . ?
C1 C6 C5 117.0(4) . . ?
C1 C6 C7 123.3(4) . . ?
C5 C6 C7 119.7(4) . . ?
O1 C1 C2 119.2(4) . . ?
O1 C1 C6 121.0(4) . . ?
C2 C1 C6 119.8(4) . . ?
C3 C2 C1 120.6(4) . . ?
C4 C5 C6 122.3(4) . . ?
N1 C7 C6 122.4(4) . . ?
N1 C7 C8 120.9(4) . . ?
C6 C7 C8 116.7(4) . . ?
O2 C18 C13 123.0(4) . . ?
O2 C18 C17 118.7(4) . . ?
C13 C18 C17 118.3(4) . . ?
N1 C9 C10 114.1(4) . . ?
C16 C17 C18 120.3(5) . . ?
N2 C11 C10 108.4(4) . . ?
N2 C12 C13 127.0(4) . . ?
C15 C14 C13 121.8(5) . . ?
C4 C3 C2 120.9(5) . . ?
C11 C10 C9 114.2(4) . . ?
C17 C16 C15 121.6(5) . . ?
C5 C4 C3 119.3(4) . . ?
N5 C21 C22 178.5(7) . . ?
C14 C15 C16 118.6(5) . . ?
N6 C23 C24 179.1(10) . . ?

_refine_diff_density_max         0.604
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.071

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1811945'
_audit_update_record             
;
2018-01-23 deposited with the CCDC.
2018-01-26 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            'C18 H18.70 Cl2 Cu Mn N2 O3.35'
_chemical_formula_weight         506.03

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'
Cu Cu 0.3201 1.2651 '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                   8.481(5)
_cell_length_b                   11.101(5)
_cell_length_c                   20.649(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.972(5)
_cell_angle_gamma                90.00
_cell_volume                     1936.7(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8680
_cell_measurement_theta_min      1.980
_cell_measurement_theta_max      24.770

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.745
_exptl_crystal_F_000             1022
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    2.050
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   EMPIRICAL
_exptl_absorpt_correction_T_min  0.906
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8680
_diffrn_reflns_av_unetI/netI     0.1202
_diffrn_reflns_av_R_equivalents  0.0920
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.980
_diffrn_reflns_theta_max         24.770
_diffrn_reflns_theta_full        24.770
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             3190
_reflns_number_gt                1431
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_publication_material  'SHELXL-2016/6, PLATON, WINGX (Ferrugia, 2012)'
_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)+(0.0528P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3190
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1453
_refine_ls_R_factor_gt           0.0539
_refine_ls_wR_factor_ref         0.1345
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   0.843
_refine_ls_restrained_S_all      0.843
_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
Mn1 Mn 0.71811(13) 0.23942(9) 0.37588(5) 0.0571(4) Uani 1 1 d . . . . .
Cu1 Cu 0.80932(10) 0.23392(7) 0.53116(4) 0.0553(3) Uani 1 1 d . . . . .
Cl1 Cl 0.8362(3) 0.39382(19) 0.32038(10) 0.0868(7) Uani 1 1 d . . . . .
Cl2 Cl 0.6582(2) 0.05937(17) 0.32120(9) 0.0726(6) Uani 1 1 d . . . . .
N1 N 1.0042(8) 0.1936(5) 0.5837(3) 0.0633(18) Uani 1 1 d . . . . .
N2 N 0.6849(9) 0.2880(6) 0.6010(3) 0.072(2) Uani 1 1 d . . . . .
O1 O 0.8976(6) 0.1942(4) 0.4510(2) 0.0546(13) Uani 1 1 d . . . . .
O2 O 0.6379(6) 0.2699(4) 0.4677(2) 0.0575(13) Uani 1 1 d . . . . .
O3 O 0.4646(6) 0.3099(5) 0.3625(3) 0.0755(16) Uani 1 1 d . . . . .
C1 C 1.0311(9) 0.1403(6) 0.4412(4) 0.0529(19) Uani 1 1 d . . . . .
C2 C 1.0715(9) 0.1154(6) 0.3784(4) 0.063(2) Uani 1 1 d . . . . .
H2 H 1.002754 0.137033 0.342766 0.075 Uiso 1 1 calc R U . . .
C3 C 1.2104(11) 0.0598(7) 0.3690(4) 0.072(2) Uani 1 1 d . . . . .
H3 H 1.235804 0.044188 0.326858 0.087 Uiso 1 1 calc R U . . .
C4 C 1.3143(10) 0.0263(7) 0.4209(5) 0.082(3) Uani 1 1 d . . . . .
H4 H 1.408137 -0.012795 0.413548 0.098 Uiso 1 1 calc R U . . .
C5 C 1.2805(10) 0.0498(7) 0.4820(5) 0.082(3) Uani 1 1 d . . . . .
H5 H 1.350628 0.025757 0.516708 0.099 Uiso 1 1 calc R U . . .
C6 C 1.1410(9) 0.1099(6) 0.4940(4) 0.0539(19) Uani 1 1 d . . . . .
C7 C 1.1205(10) 0.1395(7) 0.5599(4) 0.068(2) Uani 1 1 d . . . . .
H7 H 1.202899 0.116570 0.590002 0.081 Uiso 1 1 calc R U . . .
C8 C 1.0283(11) 0.2139(8) 0.6534(4) 0.090(3) Uani 1 1 d . . . . .
H8A H 1.138076 0.235574 0.664560 0.108 Uiso 1 1 calc R U . . .
H8B H 1.008050 0.139361 0.675768 0.108 Uiso 1 1 calc R U . . .
C9 C 0.9246(13) 0.3105(8) 0.6770(4) 0.105(4) Uani 1 1 d . . . . .
H9A H 0.955907 0.326464 0.722480 0.126 Uiso 1 1 calc R U . . .
H9B H 0.940018 0.384000 0.652874 0.126 Uiso 1 1 calc R U . . .
C10 C 0.7537(12) 0.2774(8) 0.6695(4) 0.107(3) Uani 1 1 d . . . . .
H10A H 0.741577 0.195141 0.684171 0.129 Uiso 1 1 calc R U . . .
H10B H 0.695855 0.329482 0.696783 0.129 Uiso 1 1 calc R U . . .
C12 C 0.5464(12) 0.3362(7) 0.5917(5) 0.075(3) Uani 1 1 d . . . . .
H12 H 0.503859 0.362501 0.629218 0.089 Uiso 1 1 calc R U . . .
C13 C 0.4485(11) 0.3554(7) 0.5334(5) 0.070(2) Uani 1 1 d . . . . .
C14 C 0.3001(13) 0.4101(8) 0.5362(6) 0.095(4) Uani 1 1 d . . . . .
H14 H 0.265896 0.434744 0.575727 0.114 Uiso 1 1 calc R U . . .
C15 C 0.2101(12) 0.4259(9) 0.4811(7) 0.106(4) Uani 1 1 d . . . . .
H15 H 0.110754 0.460474 0.483162 0.127 Uiso 1 1 calc R U . . .
C16 C 0.2549(10) 0.3942(7) 0.4213(5) 0.081(3) Uani 1 1 d . . . . .
H16 H 0.187636 0.406424 0.383903 0.097 Uiso 1 1 calc R U . . .
C17 C 0.4015(10) 0.3439(6) 0.4181(5) 0.065(2) Uani 1 1 d . . . . .
C18 C 0.4999(10) 0.3222(6) 0.4738(4) 0.060(2) Uani 1 1 d . . . . .
C19 C 0.3758(10) 0.3343(8) 0.3011(4) 0.111(3) Uani 1 1 d . . . . .
H19A H 0.273778 0.296683 0.300408 0.166 Uiso 1 1 calc R U . . .
H19B H 0.431857 0.302677 0.266416 0.166 Uiso 1 1 calc R U . . .
H19C H 0.362841 0.419702 0.295714 0.166 Uiso 1 1 calc R U . . .
O1W O 0.6415(17) 0.6052(13) 0.2814(7) 0.093(5) Uani 0.35 1 d . . P . .
H1WA H 0.556402 0.590093 0.257114 0.140 Uiso 0.35 1 d R U P . .
H1WB H 0.680008 0.536080 0.294002 0.140 Uiso 0.35 1 d R U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 O2 2.096(4) . ?
Mn1 O1 2.137(5) . ?
Mn1 O3 2.282(5) . ?
Mn1 Cl2 2.330(2) . ?
Mn1 Cl1 2.335(2) . ?
Cu1 O2 1.913(5) . ?
Cu1 O1 1.926(4) . ?
Cu1 N1 1.949(6) . ?
Cu1 N2 1.954(7) . ?
N1 C7 1.288(9) . ?
N1 C8 1.454(9) . ?
N2 C12 1.290(10) . ?
N2 C10 1.487(10) . ?
O1 C1 1.312(8) . ?
O2 C18 1.323(8) . ?
O3 C17 1.361(9) . ?
O3 C19 1.443(8) . ?
C1 C2 1.398(9) . ?
C1 C6 1.411(9) . ?
C2 C3 1.359(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.344(11) . ?
C4 H4 0.9300 . ?
C5 C6 1.399(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.425(10) . ?
C7 H7 0.9300 . ?
C8 C9 1.495(11) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.491(11) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C12 C13 1.418(11) . ?
C12 H12 0.9300 . ?
C13 C18 1.389(10) . ?
C13 C14 1.403(11) . ?
C14 C15 1.327(12) . ?
C14 H14 0.9300 . ?
C15 C16 1.369(12) . ?
C15 H15 0.9300 . ?
C16 C17 1.369(10) . ?
C16 H16 0.9300 . ?
C17 C18 1.384(10) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
O1W H1WA 0.8587 . ?
O1W H1WB 0.8657 . ?

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 O1 69.38(18) . . ?
O2 Mn1 O3 71.2(2) . . ?
O1 Mn1 O3 140.6(2) . . ?
O2 Mn1 Cl2 120.17(14) . . ?
O1 Mn1 Cl2 105.17(14) . . ?
O3 Mn1 Cl2 94.14(15) . . ?
O2 Mn1 Cl1 120.79(14) . . ?
O1 Mn1 Cl1 102.71(14) . . ?
O3 Mn1 Cl1 97.39(15) . . ?
Cl2 Mn1 Cl1 118.47(9) . . ?
O2 Cu1 O1 77.8(2) . . ?
O2 Cu1 N1 170.6(3) . . ?
O1 Cu1 N1 93.0(3) . . ?
O2 Cu1 N2 90.8(3) . . ?
O1 Cu1 N2 168.4(3) . . ?
N1 Cu1 N2 98.4(3) . . ?
C7 N1 C8 113.8(7) . . ?
C7 N1 Cu1 122.3(6) . . ?
C8 N1 Cu1 123.7(6) . . ?
C12 N2 C10 116.9(7) . . ?
C12 N2 Cu1 124.1(6) . . ?
C10 N2 Cu1 119.0(6) . . ?
C1 O1 Cu1 129.9(4) . . ?
C1 O1 Mn1 124.4(4) . . ?
Cu1 O1 Mn1 105.3(2) . . ?
C18 O2 Cu1 130.7(5) . . ?
C18 O2 Mn1 121.1(5) . . ?
Cu1 O2 Mn1 107.4(2) . . ?
C17 O3 C19 118.4(7) . . ?
C17 O3 Mn1 115.4(5) . . ?
C19 O3 Mn1 125.8(5) . . ?
O1 C1 C2 121.2(7) . . ?
O1 C1 C6 120.7(7) . . ?
C2 C1 C6 118.1(7) . . ?
C3 C2 C1 120.5(8) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 121.0(8) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 120.3(9) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.7(9) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 119.3(8) . . ?
C5 C6 C7 117.0(8) . . ?
C1 C6 C7 123.7(7) . . ?
N1 C7 C6 129.3(8) . . ?
N1 C7 H7 115.4 . . ?
C6 C7 H7 115.4 . . ?
N1 C8 C9 113.4(7) . . ?
N1 C8 H8A 108.9 . . ?
C9 C8 H8A 108.9 . . ?
N1 C8 H8B 108.9 . . ?
C9 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C10 C9 C8 112.5(8) . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
N2 C10 C9 112.2(7) . . ?
N2 C10 H10A 109.2 . . ?
C9 C10 H10A 109.2 . . ?
N2 C10 H10B 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
N2 C12 C13 130.4(8) . . ?
N2 C12 H12 114.8 . . ?
C13 C12 H12 114.8 . . ?
C18 C13 C14 120.3(9) . . ?
C18 C13 C12 120.4(9) . . ?
C14 C13 C12 119.4(9) . . ?
C15 C14 C13 118.2(11) . . ?
C15 C14 H14 120.9 . . ?
C13 C14 H14 120.9 . . ?
C14 C15 C16 123.8(11) . . ?
C14 C15 H15 118.1 . . ?
C16 C15 H15 118.1 . . ?
C15 C16 C17 118.3(10) . . ?
C15 C16 H16 120.9 . . ?
C17 C16 H16 120.9 . . ?
O3 C17 C16 125.4(9) . . ?
O3 C17 C18 113.6(7) . . ?
C16 C17 C18 121.0(9) . . ?
O2 C18 C17 118.1(8) . . ?
O2 C18 C13 123.4(8) . . ?
C17 C18 C13 118.5(9) . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
H1WA O1W H1WB 106.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1WB Cl1 0.87 2.10 2.942(14) 163.1 .
O1W H1WA Cl2 0.86 2.35 3.205(14) 172.1 2_655

_refine_diff_density_max         0.328
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.086

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1811946'
_audit_update_record             
;
2018-01-23 deposited with the CCDC.
2018-01-26 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 H20 Cl2 Cu Mn N2 O3'
_chemical_formula_weight         513.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Cu Cu 0.3201 1.2651 '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'

_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                   11.2555(13)
_cell_length_b                   12.524(3)
_cell_length_c                   14.510(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.073(14)
_cell_angle_gamma                90
_cell_volume                     2007.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    15738
_cell_measurement_theta_min      3.49
_cell_measurement_theta_max      30.00

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20

_exptl_crystal_density_diffrn    1.700
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_coefficient_mu    1.978
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'ABSPACK, Oxford Diffraction Ltd'
_exptl_absorpt_correction_T_min  0.897
_exptl_absorpt_correction_T_max  1.000

_diffrn_ambient_temperature      150(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  'Oxford Diffaction X-Calibor System'
_diffrn_measurement_method       '321 frames, counting time 10 s.'
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  n/a
_diffrn_standards_decay_%        n/a
_diffrn_reflns_number            15738
_diffrn_reflns_av_unetI/netI     0.1211
_diffrn_reflns_av_R_equivalents  0.1153
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.494
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             5760
_reflns_number_gt                3273
_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       'Crysalis, Oxford Diffraction'
_computing_cell_refinement       'Crysalis, Oxford Diffraction'
_computing_data_reduction        'Crysalis, Oxford Diffraction'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_publication_material  'SHELXL, PLATON, WINGX (Ferrugia, 2012)'

_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1072P)²] 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         5760
_refine_ls_number_parameters     259
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1486
_refine_ls_R_factor_gt           0.0805
_refine_ls_wR_factor_ref         0.2278
_refine_ls_wR_factor_gt          0.1918
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.033
_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
Mn2 Mn -0.05456(7) 0.65871(6) 0.23733(6) 0.0392(2) Uani 1 1 d . . . . .
Cu1 Cu 0.18160(5) 0.57961(5) 0.16185(5) 0.0394(2) Uani 1 1 d . . . . .
Cl1 Cl -0.03213(16) 0.79816(12) 0.34489(13) 0.0618(5) Uani 1 1 d . . . . .
Cl2 Cl -0.21381(13) 0.54229(13) 0.24517(13) 0.0577(4) Uani 1 1 d . . . . .
N1 N 0.3457(4) 0.5548(4) 0.2257(4) 0.0502(12) Uani 1 1 d D . . . .
N2 N 0.2148(4) 0.5653(3) 0.0377(3) 0.0403(10) Uani 1 1 d D . . . .
O1 O 0.1203(3) 0.5759(3) 0.2751(3) 0.0396(8) Uani 1 1 d . . . . .
O2 O 0.0293(3) 0.6466(3) 0.1191(3) 0.0424(9) Uani 1 1 d . . . . .
O3 O -0.1700(3) 0.7475(3) 0.1012(3) 0.0514(10) Uani 1 1 d . . . . .
C1 C 0.1624(5) 0.5045(4) 0.3419(4) 0.0389(12) Uani 1 1 d . . . . .
C2 C 0.0844(5) 0.4672(5) 0.3997(4) 0.0467(14) Uani 1 1 d . . . . .
H2 H 0.005206 0.492369 0.389795 0.056 Uiso 1 1 calc R U . . .
C3 C 0.1214(6) 0.3948(4) 0.4700(5) 0.0523(15) Uani 1 1 d . . . . .
H3 H 0.067886 0.371690 0.507312 0.063 Uiso 1 1 calc R U . . .
C4 C 0.2383(6) 0.3562(5) 0.4854(5) 0.0580(17) Uani 1 1 d . . . . .
H4 H 0.263999 0.306105 0.532297 0.070 Uiso 1 1 calc R U . . .
C5 C 0.3162(6) 0.3927(5) 0.4304(5) 0.0542(16) Uani 1 1 d . . . . .
H5 H 0.394986 0.366433 0.441685 0.065 Uiso 1 1 calc R U . . .
C6 C 0.2839(5) 0.4669(4) 0.3586(4) 0.0425(13) Uani 1 1 d . . . . .
C7 C 0.3746(5) 0.5097(5) 0.3067(5) 0.0502(15) Uani 1 1 d . . . . .
C8 C 0.5063(5) 0.4991(7) 0.3544(6) 0.077(2) Uani 1 1 d . . . . .
H8A H 0.510963 0.481327 0.419398 0.116 Uiso 1 1 calc DR U . . .
H8B H 0.547339 0.565540 0.349832 0.116 Uiso 1 1 calc DR U . . .
H8C H 0.543947 0.443789 0.324351 0.116 Uiso 1 1 calc DR U . . .
C9A C 0.4186(12) 0.6300(12) 0.1772(9) 0.049(2) Uani 0.467(12) 1 d D . P A 1
H9A1 H 0.379625 0.699456 0.171096 0.058 Uiso 0.467(12) 1 calc R U P A 1
H9A2 H 0.498424 0.638640 0.215920 0.058 Uiso 0.467(12) 1 calc R U P A 1
C10A C 0.4313(5) 0.5925(7) 0.0840(5) 0.068(2) Uani 0.467(12) 1 d D . P A 1
H10A H 0.507250 0.553894 0.091059 0.082 Uiso 0.467(12) 1 calc R U P A 1
H10B H 0.438324 0.654778 0.045744 0.082 Uiso 0.467(12) 1 calc R U P A 1
C9B C 0.4568(10) 0.5763(11) 0.1867(8) 0.049(2) Uani 0.533(12) 1 d D . P A 2
H9B1 H 0.496571 0.639498 0.216703 0.058 Uiso 0.533(12) 1 calc R U P A 2
H9B2 H 0.512206 0.516745 0.201766 0.058 Uiso 0.533(12) 1 calc DR U P A 2
C10B C 0.4313(5) 0.5925(7) 0.0840(5) 0.068(2) Uani 0.533(12) 1 d D . P A 2
H10C H 0.505381 0.580290 0.060746 0.082 Uiso 0.533(12) 1 calc R U P A 2
H10D H 0.408185 0.666400 0.071271 0.082 Uiso 0.533(12) 1 calc R U P A 2
C11 C 0.3326(5) 0.5213(5) 0.0294(5) 0.0608(18) Uani 1 1 d D . . . .
H11A H 0.339692 0.518632 -0.036172 0.073 Uiso 1 1 calc R U . A 1
H11B H 0.340720 0.449318 0.054380 0.073 Uiso 1 1 calc R U . A 1
C12 C 0.1418(5) 0.5881(4) -0.0391(4) 0.0448(13) Uani 1 1 d . . . . .
H12 H 0.167561 0.572042 -0.094726 0.054 Uiso 1 1 calc R U . . .
C13 C 0.0220(5) 0.6368(4) -0.0477(4) 0.0400(12) Uani 1 1 d . . . . .
C14 C -0.0445(6) 0.6549(5) -0.1386(5) 0.0536(15) Uani 1 1 d . . . . .
H14 H -0.014499 0.633401 -0.191101 0.064 Uiso 1 1 calc R U . . .
C15 C -0.1567(6) 0.7058(5) -0.1485(5) 0.0596(18) Uani 1 1 d . . . . .
H15 H -0.201933 0.717817 -0.208324 0.072 Uiso 1 1 calc R U . . .
C16 C -0.2023(5) 0.7391(4) -0.0700(5) 0.0522(16) Uani 1 1 d . . . . .
H16 H -0.276800 0.773498 -0.077535 0.063 Uiso 1 1 calc R U . . .
C17 C -0.1365(5) 0.7205(4) 0.0178(4) 0.0434(13) Uani 1 1 d . . . . .
C18 C -0.0246(4) 0.6654(4) 0.0315(4) 0.0360(11) Uani 1 1 d . . . . .
C19 C -0.2835(6) 0.8050(6) 0.0983(6) 0.072(2) Uani 1 1 d . . . . .
H19A H -0.279768 0.872627 0.067764 0.108 Uiso 1 1 calc R U . . .
H19B H -0.295997 0.816459 0.161104 0.108 Uiso 1 1 calc R U . . .
H19C H -0.349279 0.763755 0.063958 0.108 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn2 O2 2.116(4) . ?
Mn2 O1 2.199(3) . ?
Mn2 Cl1 2.3233(18) . ?
Mn2 Cl2 2.3302(17) . ?
Mn2 O3 2.417(4) . ?
Cu1 O1 1.902(4) . ?
Cu1 O2 1.902(3) . ?
Cu1 N2 1.917(5) . ?
Cu1 N1 1.926(5) . ?
N1 C7 1.288(8) . ?
N1 C9B 1.492(11) . ?
N1 C9A 1.508(12) . ?
N2 C12 1.283(7) . ?
N2 C11 1.462(7) . ?
O1 C1 1.336(6) . ?
O2 C18 1.321(6) . ?
O3 C17 1.377(8) . ?
O3 C19 1.459(7) . ?
C1 C2 1.406(8) . ?
C1 C6 1.421(7) . ?
C2 C3 1.369(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.481(9) . ?
C7 C8 1.517(8) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9A C10A 1.465(13) . ?
C9A H9A1 0.9700 . ?
C9A H9A2 0.9700 . ?
C10A C11 1.523(8) . ?
C10A H10A 0.9700 . ?
C10A H10B 0.9700 . ?
C9B C10B 1.476(12) . ?
C9B H9B1 0.9700 . ?
C9B H9B2 0.9700 . ?
C10B C11 1.523(8) . ?
C10B H10C 0.9700 . ?
C10B H10D 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.464(8) . ?
C12 H12 0.9300 . ?
C13 C18 1.399(8) . ?
C13 C14 1.404(8) . ?
C14 C15 1.398(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.400(10) . ?
C15 H15 0.9300 . ?
C16 C17 1.365(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.416(7) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
O2 Mn2 O1 69.58(14) . . ?
O2 Mn2 Cl1 126.20(12) . . ?
O1 Mn2 Cl1 102.15(11) . . ?
O2 Mn2 Cl2 117.50(12) . . ?
O1 Mn2 Cl2 110.65(11) . . ?
Cl1 Mn2 Cl2 115.02(7) . . ?
O2 Mn2 O3 67.93(14) . . ?
O1 Mn2 O3 137.39(15) . . ?
Cl1 Mn2 O3 100.08(11) . . ?
Cl2 Mn2 O3 91.72(11) . . ?
O1 Cu1 O2 80.72(16) . . ?
O1 Cu1 N2 168.11(17) . . ?
O2 Cu1 N2 93.51(18) . . ?
O1 Cu1 N1 93.10(19) . . ?
O2 Cu1 N1 161.61(19) . . ?
N2 Cu1 N1 95.4(2) . . ?
C7 N1 C9B 110.0(6) . . ?
C7 N1 C9A 129.4(7) . . ?
C7 N1 Cu1 124.0(4) . . ?
C9B N1 Cu1 125.8(6) . . ?
C9A N1 Cu1 103.4(7) . . ?
C12 N2 C11 116.8(5) . . ?
C12 N2 Cu1 126.0(4) . . ?
C11 N2 Cu1 117.2(4) . . ?
C1 O1 Cu1 120.4(3) . . ?
C1 O1 Mn2 132.2(3) . . ?
Cu1 O1 Mn2 103.21(16) . . ?
C18 O2 Cu1 127.7(4) . . ?
C18 O2 Mn2 125.0(3) . . ?
Cu1 O2 Mn2 106.39(18) . . ?
C17 O3 C19 118.8(5) . . ?
C17 O3 Mn2 114.2(3) . . ?
C19 O3 Mn2 125.5(5) . . ?
O1 C1 C2 118.6(5) . . ?
O1 C1 C6 122.7(5) . . ?
C2 C1 C6 118.6(5) . . ?
C3 C2 C1 121.9(5) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C2 C3 C4 119.8(6) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 119.0(6) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 123.6(6) . . ?
C4 C5 H5 118.2 . . ?
C6 C5 H5 118.2 . . ?
C5 C6 C1 117.0(6) . . ?
C5 C6 C7 121.0(5) . . ?
C1 C6 C7 121.8(5) . . ?
N1 C7 C6 123.1(5) . . ?
N1 C7 C8 120.5(6) . . ?
C6 C7 C8 116.4(6) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10A C9A N1 112.8(9) . . ?
C10A C9A H9A1 109.0 . . ?
N1 C9A H9A1 109.0 . . ?
C10A C9A H9A2 109.0 . . ?
N1 C9A H9A2 109.0 . . ?
H9A1 C9A H9A2 107.8 . . ?
C9A C10A C11 118.5(7) . . ?
C9A C10A H10A 107.7 . . ?
C11 C10A H10A 107.7 . . ?
C9A C10A H10B 107.7 . . ?
C11 C10A H10B 107.7 . . ?
H10A C10A H10B 107.1 . . ?
C10B C9B N1 113.1(8) . . ?
C10B C9B H9B1 109.0 . . ?
N1 C9B H9B1 109.0 . . ?
C10B C9B H9B2 109.0 . . ?
N1 C9B H9B2 109.0 . . ?
H9B1 C9B H9B2 107.8 . . ?
C9B C10B C11 115.3(7) . . ?
C9B C10B H10C 108.5 . . ?
C11 C10B H10C 108.5 . . ?
C9B C10B H10D 108.5 . . ?
C11 C10B H10D 108.5 . . ?
H10C C10B H10D 107.5 . . ?
N2 C11 C10B 108.6(5) . . ?
N2 C11 C10A 108.6(5) . . ?
N2 C11 H11A 110.0 . . ?
C10A C11 H11A 110.0 . . ?
N2 C11 H11B 110.0 . . ?
C10A C11 H11B 110.0 . . ?
H11A C11 H11B 108.4 . . ?
N2 C12 C13 126.3(6) . . ?
N2 C12 H12 116.8 . . ?
C13 C12 H12 116.8 . . ?
C18 C13 C14 121.0(5) . . ?
C18 C13 C12 121.4(5) . . ?
C14 C13 C12 117.6(6) . . ?
C15 C14 C13 118.5(6) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C14 C15 C16 121.2(6) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C17 C16 C15 119.4(6) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 O3 125.9(5) . . ?
C16 C17 C18 121.6(6) . . ?
O3 C17 C18 112.5(5) . . ?
O2 C18 C13 124.8(5) . . ?
O2 C18 C17 117.0(5) . . ?
C13 C18 C17 118.2(5) . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_refine_diff_density_max         0.786
_refine_diff_density_min         -0.946
_refine_diff_density_rms         0.180

