# 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 2017

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

data_MKD-723
_database_code_depnum_ccdc_archive 'CCDC 1522496'
_audit_update_record             
;
2017-08-05 deposited with the CCDC.
2017-08-15 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         'C18 H18 Cl Mn N2 O4'
_chemical_formula_sum            'C18 H18 Cl Mn N2 O4'
_chemical_formula_weight         416.73

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 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'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   17.786(8)
_cell_length_b                   10.318(5)
_cell_length_c                   19.201(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3524(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    211
_cell_measurement_theta_min      2.12
_cell_measurement_theta_max      25.60

_exptl_crystal_description       Rod-Shape
_exptl_crystal_colour            Dark-Green
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_F_000             1712.0
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.927
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.723
_exptl_absorpt_correction_T_max  0.793
_exptl_absorpt_process_details   SADABS
_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-II CCD'
_diffrn_reflns_number            21132
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_av_R_equivalents  0.0811
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.121
_diffrn_reflns_theta_max         25.598
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3324
_reflns_number_gt                2116
_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 APEX II CCD'
_computing_cell_refinement       'BRUKER SMART APEX II CCD'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury 3.2'
_computing_publication_material  'WINGX V1.80.01'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0357P)²+7.6591P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3324
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1328
_refine_ls_wR_factor_gt          0.1091
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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 0.86820(4) 0.26241(6) 0.66229(3) 0.0370(2) Uani 1 1 d . . . . .
Cl1 Cl 0.86735(7) 0.15407(11) 0.77196(6) 0.0499(3) Uani 1 1 d . . . . .
O1 O 1.18344(18) -0.0019(4) 0.57698(18) 0.0606(10) Uani 1 1 d . . . . .
O2 O 0.94383(16) 0.1718(3) 0.61672(16) 0.0471(8) Uani 1 1 d . . . . .
O3 O 0.57279(17) 0.0736(4) 0.49257(18) 0.0566(9) Uani 1 1 d . . . . .
O4 O 0.79613(16) 0.1738(3) 0.61082(16) 0.0421(8) Uani 1 1 d . . . . .
N1 N 0.7942(2) 0.3916(3) 0.68854(18) 0.0392(9) Uani 1 1 d . . . . .
N2 N 0.9379(2) 0.4002(3) 0.68825(19) 0.0413(9) Uani 1 1 d . . . . .
C19 C 0.6046(3) -0.0413(6) 0.4657(3) 0.0644(16) Uani 1 1 d . . . . .
H19A H 0.6505 -0.0209 0.4417 0.097 Uiso 1 1 calc R U . . .
H19B H 0.5700 -0.0811 0.4339 0.097 Uiso 1 1 calc R U . . .
H19C H 0.6152 -0.0999 0.5033 0.097 Uiso 1 1 calc R U . . .
C1 C 0.8253(3) 0.4846(5) 0.7382(3) 0.0536(13) Uani 1 1 d . . . . .
H1A H 0.8272 0.4467 0.7844 0.064 Uiso 1 1 calc R U . . .
H1B H 0.7940 0.5615 0.7400 0.064 Uiso 1 1 calc R U . . .
C2 C 0.9021(3) 0.5189(4) 0.7145(3) 0.0531(13) Uani 1 1 d . . . . .
H2A H 0.8996 0.5835 0.6778 0.064 Uiso 1 1 calc R U . . .
H2B H 0.9310 0.5543 0.7529 0.064 Uiso 1 1 calc R U . . .
C3 C 1.0093(3) 0.3927(5) 0.6848(2) 0.0469(12) Uani 1 1 d . . . . .
H3 H 1.0365 0.4630 0.7017 0.056 Uiso 1 1 calc R U . . .
C4 C 1.0508(2) 0.2883(4) 0.6578(2) 0.0419(11) Uani 1 1 d . . . . .
C5 C 1.0168(2) 0.1824(5) 0.6242(2) 0.0405(11) Uani 1 1 d . . . . .
C6 C 1.0604(2) 0.0844(5) 0.5968(2) 0.0439(12) Uani 1 1 d . . . . .
H6 H 1.0377 0.0138 0.5753 0.053 Uiso 1 1 calc R U . . .
C7 C 1.1371(3) 0.0910(5) 0.6013(2) 0.0481(12) Uani 1 1 d . . . . .
C8 C 1.1509(3) -0.1184(6) 0.5526(3) 0.0651(16) Uani 1 1 d . . . . .
H8A H 1.1184 -0.1534 0.5878 0.098 Uiso 1 1 calc R U . . .
H8B H 1.1899 -0.1797 0.5422 0.098 Uiso 1 1 calc R U . . .
H8C H 1.1224 -0.1012 0.5112 0.098 Uiso 1 1 calc R U . . .
C9 C 1.1719(3) 0.1968(5) 0.6329(3) 0.0542(14) Uani 1 1 d . . . . .
H9 H 1.2240 0.2019 0.6351 0.065 Uiso 1 1 calc R U . . .
C10 C 1.1293(3) 0.2908(5) 0.6600(3) 0.0527(13) Uani 1 1 d . . . . .
H10 H 1.1529 0.3609 0.6812 0.063 Uiso 1 1 calc R U . . .
C11 C 0.7257(3) 0.3988(4) 0.6692(2) 0.0419(11) Uani 1 1 d . . . . .
H11 H 0.6970 0.4667 0.6869 0.050 Uiso 1 1 calc R U . . .
C12 C 0.6900(2) 0.3122(4) 0.6232(2) 0.0394(11) Uani 1 1 d . . . . .
C13 C 0.6152(3) 0.3363(5) 0.6040(3) 0.0509(13) Uani 1 1 d . . . . .
H13 H 0.5907 0.4089 0.6216 0.061 Uiso 1 1 calc R U . . .
C14 C 0.5784(3) 0.2563(5) 0.5607(3) 0.0529(13) Uani 1 1 d . . . . .
H14 H 0.5290 0.2739 0.5481 0.063 Uiso 1 1 calc R U . . .
C15 C 0.6143(2) 0.1477(5) 0.5348(2) 0.0439(12) Uani 1 1 d . . . . .
C16 C 0.6876(2) 0.1219(4) 0.5518(2) 0.0378(10) Uani 1 1 d . . . . .
H16 H 0.7113 0.0494 0.5333 0.045 Uiso 1 1 calc R U . . .
C18 C 0.7260(2) 0.2028(4) 0.5960(2) 0.0368(11) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 O2 1.857(3) . ?
Mn1 O4 1.859(3) . ?
Mn1 N1 1.939(4) . ?
Mn1 N2 1.951(4) . ?
Mn1 Cl1 2.3841(16) . ?
O1 C7 1.347(6) . ?
O1 C8 1.414(6) . ?
O2 C5 1.310(5) . ?
O3 C15 1.337(5) . ?
O3 C19 1.411(6) . ?
O4 C18 1.313(5) . ?
N1 C11 1.277(5) . ?
N1 C1 1.461(5) . ?
N2 C3 1.273(6) . ?
N2 C2 1.470(6) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C1 C2 1.483(7) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.406(6) . ?
C3 H3 0.9300 . ?
C4 C10 1.396(6) . ?
C4 C5 1.406(6) . ?
C5 C6 1.378(6) . ?
C6 C7 1.370(6) . ?
C6 H6 0.9300 . ?
C7 C9 1.393(7) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.336(7) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.407(6) . ?
C11 H11 0.9300 . ?
C12 C18 1.398(6) . ?
C12 C13 1.404(6) . ?
C13 C14 1.342(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.382(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.369(6) . ?
C16 C18 1.374(6) . ?
C16 H16 0.9300 . ?

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 O4 90.08(13) . . ?
O2 Mn1 N1 163.69(16) . . ?
O4 Mn1 N1 90.47(14) . . ?
O2 Mn1 N2 91.52(15) . . ?
O4 Mn1 N2 158.81(15) . . ?
N1 Mn1 N2 82.21(16) . . ?
O2 Mn1 Cl1 100.65(11) . . ?
O4 Mn1 Cl1 103.57(11) . . ?
N1 Mn1 Cl1 95.07(12) . . ?
N2 Mn1 Cl1 96.89(12) . . ?
C7 O1 C8 118.0(4) . . ?
C5 O2 Mn1 128.6(3) . . ?
C15 O3 C19 118.7(4) . . ?
C18 O4 Mn1 131.1(3) . . ?
C11 N1 C1 120.8(4) . . ?
C11 N1 Mn1 127.8(3) . . ?
C1 N1 Mn1 111.4(3) . . ?
C3 N2 C2 120.0(4) . . ?
C3 N2 Mn1 125.2(3) . . ?
C2 N2 Mn1 114.7(3) . . ?
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 . . ?
N1 C1 C2 107.7(4) . . ?
N1 C1 H1A 110.2 . . ?
C2 C1 H1A 110.2 . . ?
N1 C1 H1B 110.2 . . ?
C2 C1 H1B 110.2 . . ?
H1A C1 H1B 108.5 . . ?
N2 C2 C1 107.8(4) . . ?
N2 C2 H2A 110.1 . . ?
C1 C2 H2A 110.1 . . ?
N2 C2 H2B 110.1 . . ?
C1 C2 H2B 110.1 . . ?
H2A C2 H2B 108.5 . . ?
N2 C3 C4 126.1(4) . . ?
N2 C3 H3 116.9 . . ?
C4 C3 H3 116.9 . . ?
C10 C4 C3 120.0(4) . . ?
C10 C4 C5 117.3(5) . . ?
C3 C4 C5 122.6(4) . . ?
O2 C5 C6 117.0(4) . . ?
O2 C5 C4 122.8(4) . . ?
C6 C5 C4 120.2(4) . . ?
C7 C6 C5 120.0(5) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
O1 C7 C6 123.5(5) . . ?
O1 C7 C9 115.9(4) . . ?
C6 C7 C9 120.5(5) . . ?
O1 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C7 119.2(5) . . ?
C10 C9 H9 120.4 . . ?
C7 C9 H9 120.4 . . ?
C9 C10 C4 122.8(5) . . ?
C9 C10 H10 118.6 . . ?
C4 C10 H10 118.6 . . ?
N1 C11 C12 125.1(4) . . ?
N1 C11 H11 117.4 . . ?
C12 C11 H11 117.4 . . ?
C18 C12 C13 118.7(4) . . ?
C18 C12 C11 122.7(4) . . ?
C13 C12 C11 118.6(4) . . ?
C14 C13 C12 121.0(5) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 119.8(4) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
O3 C15 C16 124.0(4) . . ?
O3 C15 C14 115.3(4) . . ?
C16 C15 C14 120.8(4) . . ?
C15 C16 C18 120.2(4) . . ?
C15 C16 H16 119.9 . . ?
C18 C16 H16 119.9 . . ?
O4 C18 C16 117.9(4) . . ?
O4 C18 C12 122.5(4) . . ?
C16 C18 C12 119.5(4) . . ?

_refine_diff_density_max         0.412
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_mkd-433
_database_code_depnum_ccdc_archive 'CCDC 900539'
_audit_update_record             
;
2017-08-05 deposited with the CCDC.
2017-08-15 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         'C18 H18 Mn N5 O4'
_chemical_formula_sum            'C18 H18 Mn N5 O4'
_chemical_formula_weight         423.31

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 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'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   18.1502(8)
_cell_length_b                   10.0629(4)
_cell_length_c                   20.4381(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3732.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    220
_cell_measurement_theta_min      1.99
_cell_measurement_theta_max      28.56

_exptl_crystal_description       'Block shaple'
_exptl_crystal_colour            Brown
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_F_000             1744
_exptl_absorpt_coefficient_mu    0.743
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.867
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_process_details   SADABS
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER SMART APEX-II CCD'
_diffrn_reflns_number            58033
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.993
_diffrn_reflns_theta_max         28.557
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4758
_reflns_number_gt                2591
_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 APEX II CCD'
_computing_cell_refinement       'BRUKER SMART APEX II CCD'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury 3.2'
_computing_publication_material  'WINGX V1.80.01'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0740P)²+2.6620P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4758
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1282
_refine_ls_R_factor_gt           0.0634
_refine_ls_wR_factor_ref         0.1800
_refine_ls_wR_factor_gt          0.1538
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 0.13167(3) 0.22291(5) 0.16353(3) 0.0540(2) Uani 1 1 d . . . . .
O1 O 0.42737(14) 0.4216(3) 0.00957(16) 0.0808(9) Uani 1 1 d . . . . .
O4 O -0.18010(16) 0.4710(3) 0.06603(16) 0.0879(9) Uani 1 1 d . . . . .
N2 N 0.0641(2) 0.0831(3) 0.19377(15) 0.0596(8) Uani 1 1 d . . . . .
N1 N 0.20553(19) 0.0966(3) 0.19517(14) 0.0564(8) Uani 1 1 d . . . . .
O2 O 0.20339(13) 0.3139(2) 0.11589(13) 0.0593(7) Uani 1 1 d . . . . .
O3 O 0.05766(14) 0.3070(3) 0.11624(15) 0.0716(8) Uani 1 1 d . . . . .
C1 C 0.0999(3) -0.0335(4) 0.2243(2) 0.0756(13) Uani 1 1 d . . . . .
H1A H 0.1024 -0.1062 0.1931 0.091 Uiso 1 1 calc R U . . .
H1B H 0.0716 -0.0628 0.2618 0.091 Uiso 1 1 calc R U . . .
C2 C 0.1752(3) 0.0052(4) 0.2449(2) 0.0746(12) Uani 1 1 d . . . . .
H2A H 0.1735 0.0489 0.2872 0.090 Uiso 1 1 calc R U . . .
H2B H 0.2062 -0.0730 0.2487 0.090 Uiso 1 1 calc R U . . .
C3 C 0.2736(2) 0.0899(3) 0.17797(18) 0.0579(10) Uani 1 1 d . . . . .
H3 H 0.3018 0.0224 0.1964 0.070 Uiso 1 1 calc R U . . .
C4 C 0.3098(2) 0.1767(3) 0.13330(18) 0.0528(9) Uani 1 1 d . . . . .
C5 C 0.2737(2) 0.2865(3) 0.10491(17) 0.0502(8) Uani 1 1 d . . . . .
C6 C 0.3128(2) 0.3704(4) 0.06374(17) 0.0536(9) Uani 1 1 d . . . . .
H6 H 0.2895 0.4441 0.0457 0.064 Uiso 1 1 calc R U . . .
C7 C 0.3853(2) 0.3463(4) 0.0493(2) 0.0606(10) Uani 1 1 d . . . . .
C8 C 0.4213(2) 0.2358(4) 0.0767(2) 0.0751(13) Uani 1 1 d . . . . .
H8 H 0.4703 0.2186 0.0666 0.090 Uiso 1 1 calc R U . . .
C9 C 0.3842(2) 0.1549(4) 0.1177(2) 0.0683(11) Uani 1 1 d . . . . .
H9 H 0.4085 0.0827 0.1362 0.082 Uiso 1 1 calc R U . . .
C10 C 0.3950(2) 0.5374(5) -0.0182(2) 0.0828(14) Uani 1 1 d . . . . .
H10A H 0.3505 0.5135 -0.0407 0.124 Uiso 1 1 calc R U . . .
H10B H 0.4288 0.5771 -0.0485 0.124 Uiso 1 1 calc R U . . .
H10C H 0.3837 0.5997 0.0159 0.124 Uiso 1 1 calc R U . . .
C11 C -0.0061(3) 0.0889(3) 0.18925(19) 0.0653(11) Uani 1 1 d . . . . .
H11 H -0.0324 0.0205 0.2089 0.078 Uiso 1 1 calc R U . . .
C12 C -0.0483(2) 0.1896(4) 0.15718(19) 0.0607(10) Uani 1 1 d . . . . .
C13 C -0.0148(2) 0.2949(4) 0.12181(19) 0.0575(10) Uani 1 1 d . . . . .
C14 C -0.0588(2) 0.3895(4) 0.09080(19) 0.0629(10) Uani 1 1 d . . . . .
H14 H -0.0368 0.4591 0.0681 0.075 Uiso 1 1 calc R U . . .
C15 C -0.1335(2) 0.3807(5) 0.0936(2) 0.0660(11) Uani 1 1 d . . . . .
C16 C -0.1681(2) 0.2757(5) 0.1280(2) 0.0784(13) Uani 1 1 d . . . . .
H16 H -0.2192 0.2699 0.1298 0.094 Uiso 1 1 calc R U . . .
C17 C -0.1255(2) 0.1842(5) 0.1582(2) 0.0748(13) Uani 1 1 d . . . . .
H17 H -0.1483 0.1149 0.1805 0.090 Uiso 1 1 calc R U . . .
C18 C -0.1483(3) 0.5826(6) 0.0327(3) 0.1005(18) Uani 1 1 d . . . . .
H18A H -0.1169 0.6305 0.0622 0.151 Uiso 1 1 calc R U . . .
H18B H -0.1868 0.6402 0.0175 0.151 Uiso 1 1 calc R U . . .
H18C H -0.1199 0.5518 -0.0039 0.151 Uiso 1 1 calc R U . . .
N3 N 0.1177(7) 0.3437(14) 0.2387(5) 0.062(4) Uani 0.5 1 d . . P . .
N4 N 0.1196(4) 0.3144(6) 0.2923(3) 0.083(2) Uani 1 1 d . . . . .
N5 N 0.0997(7) 0.2780(8) 0.3444(4) 0.262(6) Uani 1 1 d . . . . .
N3A N 0.1368(6) 0.3371(10) 0.2634(6) 0.037(3) Uani 0.5 1 d . . 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 O3 1.859(3) . ?
Mn1 O2 1.866(2) . ?
Mn1 N1 1.957(3) . ?
Mn1 N2 1.966(3) . ?
Mn1 N3 1.975(13) . ?
Mn1 N3A 2.344(11) . ?
O1 C7 1.348(5) . ?
O1 C10 1.423(5) . ?
O4 C15 1.363(5) . ?
O4 C18 1.436(6) . ?
N2 C11 1.279(5) . ?
N2 C1 1.479(5) . ?
N1 C3 1.286(5) . ?
N1 C2 1.477(4) . ?
O2 C5 1.325(4) . ?
O3 C13 1.326(4) . ?
C1 C2 1.482(6) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.423(5) . ?
C3 H3 0.9300 . ?
C4 C9 1.405(5) . ?
C4 C5 1.409(5) . ?
C5 C6 1.388(5) . ?
C6 C7 1.370(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.406(6) . ?
C8 C9 1.349(6) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.429(6) . ?
C11 H11 0.9300 . ?
C12 C17 1.403(6) . ?
C12 C13 1.419(5) . ?
C13 C14 1.394(5) . ?
C14 C15 1.361(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.416(6) . ?
C16 C17 1.351(6) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
N3 N3A 0.617(12) . ?
N3 N4 1.136(12) . ?
N4 N3A 0.707(10) . ?
N4 N5 1.183(9) . ?
N5 N3A 1.885(13) . ?

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
O3 Mn1 O2 90.54(11) . . ?
O3 Mn1 N1 164.24(13) . . ?
O2 Mn1 N1 90.77(12) . . ?
O3 Mn1 N2 92.22(13) . . ?
O2 Mn1 N2 161.88(12) . . ?
N1 Mn1 N2 81.85(14) . . ?
O3 Mn1 N3 91.8(3) . . ?
O2 Mn1 N3 101.1(4) . . ?
N1 Mn1 N3 103.4(3) . . ?
N2 Mn1 N3 96.7(4) . . ?
O3 Mn1 N3A 105.0(3) . . ?
O2 Mn1 N3A 100.7(3) . . ?
N1 Mn1 N3A 90.2(3) . . ?
N2 Mn1 N3A 95.9(3) . . ?
N3 Mn1 N3A 13.2(5) . . ?
C7 O1 C10 117.8(3) . . ?
C15 O4 C18 117.9(3) . . ?
C11 N2 C1 120.3(3) . . ?
C11 N2 Mn1 124.4(3) . . ?
C1 N2 Mn1 115.3(3) . . ?
C3 N1 C2 120.9(3) . . ?
C3 N1 Mn1 127.0(3) . . ?
C2 N1 Mn1 112.1(3) . . ?
C5 O2 Mn1 131.2(2) . . ?
C13 O3 Mn1 129.1(2) . . ?
N2 C1 C2 108.4(3) . . ?
N2 C1 H1A 110.0 . . ?
C2 C1 H1A 110.0 . . ?
N2 C1 H1B 110.0 . . ?
C2 C1 H1B 110.0 . . ?
H1A C1 H1B 108.4 . . ?
N1 C2 C1 108.1(3) . . ?
N1 C2 H2A 110.1 . . ?
C1 C2 H2A 110.1 . . ?
N1 C2 H2B 110.1 . . ?
C1 C2 H2B 110.1 . . ?
H2A C2 H2B 108.4 . . ?
N1 C3 C4 125.9(3) . . ?
N1 C3 H3 117.1 . . ?
C4 C3 H3 117.1 . . ?
C9 C4 C5 118.4(3) . . ?
C9 C4 C3 119.5(3) . . ?
C5 C4 C3 122.1(4) . . ?
O2 C5 C6 118.0(3) . . ?
O2 C5 C4 122.7(3) . . ?
C6 C5 C4 119.3(3) . . ?
C7 C6 C5 120.9(3) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
O1 C7 C6 125.0(4) . . ?
O1 C7 C8 114.9(4) . . ?
C6 C7 C8 120.0(4) . . ?
C9 C8 C7 119.5(4) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C4 121.8(4) . . ?
C8 C9 H9 119.1 . . ?
C4 C9 H9 119.1 . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C12 126.8(3) . . ?
N2 C11 H11 116.6 . . ?
C12 C11 H11 116.6 . . ?
C17 C12 C13 117.6(4) . . ?
C17 C12 C11 120.1(4) . . ?
C13 C12 C11 122.2(4) . . ?
O3 C13 C14 117.8(3) . . ?
O3 C13 C12 122.5(4) . . ?
C14 C13 C12 119.8(4) . . ?
C15 C14 C13 120.5(4) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 O4 123.9(4) . . ?
C14 C15 C16 120.7(4) . . ?
O4 C15 C16 115.3(4) . . ?
C17 C16 C15 118.8(4) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C16 C17 C12 122.5(4) . . ?
C16 C17 H17 118.7 . . ?
C12 C17 H17 118.7 . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3A N3 N4 33.3(17) . . ?
N3A N3 Mn1 120(2) . . ?
N4 N3 Mn1 125.9(11) . . ?
N3A N4 N3 28.6(14) . . ?
N3A N4 N5 171.3(17) . . ?
N3 N4 N5 160.1(12) . . ?
N4 N5 N3A 3.3(6) . . ?
N3 N3A N4 118(3) . . ?
N3 N3A N5 124(2) . . ?
N4 N3A N5 5.5(11) . . ?
N3 N3A Mn1 46.9(19) . . ?
N4 N3A Mn1 123.4(12) . . ?
N5 N3A Mn1 126.6(6) . . ?

_refine_diff_density_max         0.756
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_MKD-785
_database_code_depnum_ccdc_archive 'CCDC 1522497'
_audit_update_record             
;
2017-08-05 deposited with the CCDC.
2017-08-15 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         'C18 H20 Cl Mn N2 O5'
_chemical_formula_sum            'C18 H20 Cl Mn N2 O5'
_chemical_formula_weight         434.75

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'
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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 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'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   11.9970(3)
_cell_length_b                   13.1590(4)
_cell_length_c                   22.9690(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3626.08(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    250
_cell_measurement_theta_min      1.77
_cell_measurement_theta_max      27.56

_exptl_crystal_description       Block-shape
_exptl_crystal_colour            Dark-Brown
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_F_000             1792.0
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.32
_exptl_absorpt_coefficient_mu    0.909
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.624
_exptl_absorpt_correction_T_max  0.748
_exptl_absorpt_process_details   SADABS
_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-II CCD'
_diffrn_reflns_number            55374
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.773
_diffrn_reflns_theta_max         27.561
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4189
_reflns_number_gt                3359
_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 APEX II CCD'
_computing_cell_refinement       'BRUKER SMART APEX II CCD'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury 3.2'
_computing_publication_material  'WINGX V1.80.01'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0555P)²+2.6289P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4189
_refine_ls_number_parameters     251
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1126
_refine_ls_wR_factor_gt          0.1035
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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 0.35240(3) 0.14801(3) 0.50034(2) 0.02741(12) Uani 1 1 d . . . . .
Cl1 Cl 0.33141(5) 0.33566(4) 0.47122(3) 0.03660(16) Uani 1 1 d . . . . .
O1 O 0.43852(12) 0.11152(13) 0.43450(7) 0.0335(4) Uani 1 1 d . . . . .
O2 O 0.2990(2) 0.0974(2) 0.20419(9) 0.0677(7) Uani 1 1 d . . . . .
O3 O 0.47653(12) 0.16660(13) 0.54860(7) 0.0328(4) Uani 1 1 d . . . . .
O4 O 0.51663(16) 0.14555(15) 0.78772(8) 0.0452(5) Uani 1 1 d . . . . .
N1 N 0.21084(15) 0.11612(14) 0.45896(9) 0.0297(4) Uani 1 1 d . . . . .
N2 N 0.24726(15) 0.17213(14) 0.56548(8) 0.0296(4) Uani 1 1 d . . . . .
C16 C 0.38432(19) 0.15952(18) 0.64205(10) 0.0314(5) Uani 1 1 d . . . . .
C17 C 0.47941(18) 0.16144(16) 0.60624(10) 0.0289(5) Uani 1 1 d . . . . .
C1 C 0.20073(19) 0.10576(18) 0.40417(11) 0.0350(5) Uani 1 1 d . . . . .
H1 H 0.1290 0.0973 0.3896 0.042 Uiso 1 1 calc R U . . .
C2 C 0.2906(2) 0.10605(18) 0.36297(11) 0.0346(5) Uani 1 1 d . . . . .
C3 C 0.40458(19) 0.10706(17) 0.37947(10) 0.0306(5) Uani 1 1 d . . . . .
C4 C 0.4827(2) 0.10169(19) 0.33458(11) 0.0388(6) Uani 1 1 d . . . . .
H4 H 0.5581 0.1007 0.3440 0.047 Uiso 1 1 calc R U . . .
C5 C 0.4518(2) 0.0979(2) 0.27664(12) 0.0445(6) Uani 1 1 d . . . . .
H5 H 0.5064 0.0948 0.2480 0.053 Uiso 1 1 calc R U . . .
C6 C 0.3399(2) 0.0986(2) 0.26076(12) 0.0456(7) Uani 1 1 d . . . . .
C7 C 0.2618(2) 0.1026(2) 0.30385(12) 0.0426(6) Uani 1 1 d . . . . .
H7 H 0.1867 0.1030 0.2936 0.051 Uiso 1 1 calc R U . . .
C8 C 0.11253(19) 0.1105(2) 0.49717(11) 0.0369(6) Uani 1 1 d . . . . .
H8A H 0.1041 0.0423 0.5127 0.044 Uiso 1 1 calc R U . . .
H8B H 0.0456 0.1279 0.4757 0.044 Uiso 1 1 calc R U . . .
C9 C 0.13170(18) 0.1856(2) 0.54599(11) 0.0355(5) Uani 1 1 d . . . . .
H9A H 0.1201 0.2545 0.5322 0.043 Uiso 1 1 calc R U . . .
H9B H 0.0805 0.1727 0.5778 0.043 Uiso 1 1 calc R U . . .
C10 C 0.27252(19) 0.16943(18) 0.61939(10) 0.0332(5) Uani 1 1 d . . . . .
H10 H 0.2146 0.1742 0.6461 0.040 Uiso 1 1 calc R U . . .
C11 C 0.58398(19) 0.16034(19) 0.63388(11) 0.0345(5) Uani 1 1 d . . . . .
H11 H 0.6485 0.1621 0.6114 0.041 Uiso 1 1 calc R U . . .
C12 C 0.5925(2) 0.1568(2) 0.69327(11) 0.0381(6) Uani 1 1 d . . . . .
H12 H 0.6627 0.1575 0.7104 0.046 Uiso 1 1 calc R U . . .
C13 C 0.4978(2) 0.15219(18) 0.72873(11) 0.0349(5) Uani 1 1 d . . . . .
C14 C 0.3950(2) 0.15432(19) 0.70305(11) 0.0355(5) Uani 1 1 d . . . . .
H14 H 0.3314 0.1523 0.7261 0.043 Uiso 1 1 calc R U . . .
C15 C 0.4196(2) 0.1381(2) 0.82332(11) 0.0471(7) Uani 1 1 d . . . . .
H15A H 0.3760 0.1988 0.8194 0.071 Uiso 1 1 calc R U . . .
H15B H 0.4414 0.1298 0.8632 0.071 Uiso 1 1 calc R U . . .
H15C H 0.3761 0.0805 0.8113 0.071 Uiso 1 1 calc R U . . .
C18 C 0.3734(3) 0.0792(3) 0.15856(13) 0.0650(9) Uani 1 1 d . . . . .
H10A H 0.4295 0.1312 0.1582 0.098 Uiso 1 1 calc R U . . .
H10B H 0.3337 0.0799 0.1223 0.098 Uiso 1 1 calc R U . . .
H10C H 0.4079 0.0141 0.1639 0.098 Uiso 1 1 calc R U . . .
O5 O 0.35048(15) -0.02123(14) 0.53322(9) 0.0416(4) Uani 1 1 d . . . . .
H5A H 0.4147 -0.0412 0.5375 0.062 Uiso 1 1 calc R U . . .
H65 H 0.318(3) -0.056(3) 0.5126(16) 0.078(14) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 O3 1.8725(16) . ?
Mn1 O1 1.8934(16) . ?
Mn1 N2 1.9825(18) . ?
Mn1 N1 1.9910(19) . ?
Mn1 O5 2.3518(19) . ?
Mn1 Cl1 2.5706(7) . ?
O1 C3 1.329(3) . ?
O2 C6 1.389(3) . ?
O2 C18 1.397(4) . ?
O3 C17 1.326(3) . ?
O4 C13 1.377(3) . ?
O4 C15 1.426(3) . ?
N1 C1 1.272(3) . ?
N1 C8 1.472(3) . ?
N2 C10 1.275(3) . ?
N2 C9 1.468(3) . ?
C16 C17 1.407(3) . ?
C16 C14 1.409(3) . ?
C16 C10 1.445(3) . ?
C17 C11 1.406(3) . ?
C1 C2 1.434(3) . ?
C1 H1 0.9300 . ?
C2 C7 1.402(4) . ?
C2 C3 1.419(3) . ?
C3 C4 1.395(3) . ?
C4 C5 1.382(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.364(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.513(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10 0.9300 . ?
C11 C12 1.369(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.400(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.367(3) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C18 H10A 0.9600 . ?
C18 H10B 0.9600 . ?
C18 H10C 0.9600 . ?
O5 H5A 0.8200 . ?
O5 H65 0.77(4) . ?

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
O3 Mn1 O1 94.13(7) . . ?
O3 Mn1 N2 92.20(7) . . ?
O1 Mn1 N2 172.12(8) . . ?
O3 Mn1 N1 171.33(8) . . ?
O1 Mn1 N1 91.76(7) . . ?
N2 Mn1 N1 81.45(8) . . ?
O3 Mn1 O5 86.64(7) . . ?
O1 Mn1 O5 91.24(7) . . ?
N2 Mn1 O5 84.44(7) . . ?
N1 Mn1 O5 86.86(7) . . ?
O3 Mn1 Cl1 96.12(5) . . ?
O1 Mn1 Cl1 95.12(5) . . ?
N2 Mn1 Cl1 88.87(6) . . ?
N1 Mn1 Cl1 89.69(6) . . ?
O5 Mn1 Cl1 172.86(5) . . ?
C3 O1 Mn1 127.12(14) . . ?
C6 O2 C18 118.6(3) . . ?
C17 O3 Mn1 127.23(14) . . ?
C13 O4 C15 115.8(2) . . ?
C1 N1 C8 120.5(2) . . ?
C1 N1 Mn1 125.20(16) . . ?
C8 N1 Mn1 114.17(15) . . ?
C10 N2 C9 121.6(2) . . ?
C10 N2 Mn1 125.25(16) . . ?
C9 N2 Mn1 112.97(15) . . ?
C17 C16 C14 120.6(2) . . ?
C17 C16 C10 122.7(2) . . ?
C14 C16 C10 116.6(2) . . ?
O3 C17 C11 118.3(2) . . ?
O3 C17 C16 124.3(2) . . ?
C11 C17 C16 117.3(2) . . ?
N1 C1 C2 125.5(2) . . ?
N1 C1 H1 117.2 . . ?
C2 C1 H1 117.2 . . ?
C7 C2 C3 119.8(2) . . ?
C7 C2 C1 117.0(2) . . ?
C3 C2 C1 123.2(2) . . ?
O1 C3 C4 120.0(2) . . ?
O1 C3 C2 123.3(2) . . ?
C4 C3 C2 116.7(2) . . ?
C5 C4 C3 122.2(2) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 118.2(2) . . ?
C7 C6 O2 115.9(3) . . ?
C5 C6 O2 125.9(3) . . ?
C6 C7 C2 122.3(2) . . ?
C6 C7 H7 118.8 . . ?
C2 C7 H7 118.8 . . ?
N1 C8 C9 106.70(19) . . ?
N1 C8 H8A 110.4 . . ?
C9 C8 H8A 110.4 . . ?
N1 C8 H8B 110.4 . . ?
C9 C8 H8B 110.4 . . ?
H8A C8 H8B 108.6 . . ?
N2 C9 C8 106.90(19) . . ?
N2 C9 H9A 110.3 . . ?
C8 C9 H9A 110.3 . . ?
N2 C9 H9B 110.3 . . ?
C8 C9 H9B 110.3 . . ?
H9A C9 H9B 108.6 . . ?
N2 C10 C16 125.0(2) . . ?
N2 C10 H10 117.5 . . ?
C16 C10 H10 117.5 . . ?
C12 C11 C17 121.1(2) . . ?
C12 C11 H11 119.4 . . ?
C17 C11 H11 119.4 . . ?
C11 C12 C13 121.4(2) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C14 C13 O4 125.1(2) . . ?
C14 C13 C12 118.7(2) . . ?
O4 C13 C12 116.2(2) . . ?
C13 C14 C16 120.8(2) . . ?
C13 C14 H14 119.6 . . ?
C16 C14 H14 119.6 . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C18 H10A 109.5 . . ?
O2 C18 H10B 109.5 . . ?
H10A C18 H10B 109.5 . . ?
O2 C18 H10C 109.5 . . ?
H10A C18 H10C 109.5 . . ?
H10B C18 H10C 109.5 . . ?
Mn1 O5 H5A 109.5 . . ?
Mn1 O5 H65 112(3) . . ?
H5A O5 H65 111.1 . . ?

_refine_diff_density_max         0.521
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.064

