# 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 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 1841246'
_audit_update_record             
;
2018-07-24 deposited with the CCDC.
2018-07-27 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         'C26 H36 Cl Mn N4 O5, 2(H2 O)'
_chemical_formula_sum            'C26 H40 Cl Mn N4 O7'
_chemical_formula_weight         611.01

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 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 0.0059 0.0032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0105 0.0059 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3349 0.7109 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1460 0.1544 '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                   24.984(5)
_cell_length_b                   9.4500(19)
_cell_length_c                   12.221(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.64(3)
_cell_angle_gamma                90
_cell_volume                     2885.2(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3677
_cell_measurement_theta_min      1.98
_cell_measurement_theta_max      29.45

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             1288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.571
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_correction_T_min  0.822
_exptl_absorpt_correction_T_max  1.060
_exptl_absorpt_process_details   
;
 Parkin S,Moezzi B & Hope H, (1995) J. Appl. Cryst. 28, 53-56
 Cubic fit to sin(theta)/lambda - 24 parameters
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.700
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Elettra Synchrotron - XRD1 BL'
_diffrn_measurement_device_type  
;
Huber 4-circles Kappa Goniometer, Pilatus 2M detector
;
_diffrn_measurement_method       'Rotating crystal'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31391
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.606
_diffrn_reflns_theta_max         31.040
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4640
_reflns_number_gt                4385
_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       'Elettra XRD1 Data Collection SW'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS - CCP4'
_computing_structure_solution    'Sir2014 (Burla, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep3 for Windows'
_computing_publication_material  'Wingx 2013.3 (Farrugia, 1999)'

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1219P)²+15.7828P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0027(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4640
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0725
_refine_ls_wR_factor_ref         0.2311
_refine_ls_wR_factor_gt          0.2236
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_restrained_S_all      1.175
_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
Mn Mn 0.5000 0.33531(6) 0.7500 0.01286(18) Uani 1 2 d S T P . .
Cl1 Cl 0.5000 0.05977(11) 0.7500 0.0205(2) Uani 1 2 d S T P . .
N1 N 0.50351(11) 0.3284(3) 0.5831(2) 0.0147(4) Uani 1 1 d . . . . .
N2 N 0.38646(11) 0.1614(3) 0.4336(2) 0.0161(5) Uani 1 1 d . . . . .
O1 O 0.57458(9) 0.3513(3) 0.76087(19) 0.0174(4) Uani 1 1 d . . . . .
O2 O 0.27876(10) 0.0871(3) 0.3746(2) 0.0267(5) Uani 1 1 d . . . . .
O1W O 0.5000 0.5719(4) 0.7500 0.0194(6) Uani 1 2 d S T P . .
H11 H 0.524(2) 0.608(7) 0.751(5) 0.029 Uiso 1 1 d . U . . .
O2W O 0.57359(11) 0.7820(3) 0.7733(2) 0.0224(5) Uani 1 1 d . . . . .
H21 H 0.588(3) 0.791(7) 0.712(5) 0.034 Uiso 1 1 d . U . . .
H22 H 0.556(2) 0.861(7) 0.781(5) 0.034 Uiso 1 1 d . U . . .
C1 C 0.61206(12) 0.3609(3) 0.6858(3) 0.0157(5) Uani 1 1 d . . . . .
C2 C 0.66522(12) 0.3886(3) 0.7199(3) 0.0179(5) Uani 1 1 d . . . . .
H2 H 0.6731 0.4018 0.7938 0.021 Uiso 1 1 calc R U . . .
C3 C 0.70581(12) 0.3960(4) 0.6433(3) 0.0211(6) Uani 1 1 d . . . . .
H3 H 0.7407 0.4140 0.6668 0.025 Uiso 1 1 calc R U . . .
C4 C 0.69533(13) 0.3770(4) 0.5314(3) 0.0213(6) Uani 1 1 d . . . . .
H4 H 0.7230 0.3812 0.4812 0.026 Uiso 1 1 calc R U . . .
C5 C 0.64350(13) 0.3522(4) 0.4969(3) 0.0184(6) Uani 1 1 d . . . . .
H5 H 0.6363 0.3397 0.4228 0.022 Uiso 1 1 calc R U . . .
C6 C 0.60109(12) 0.3455(3) 0.5726(3) 0.0151(5) Uani 1 1 d . . . . .
C7 C 0.54777(12) 0.3291(3) 0.5288(3) 0.0153(5) Uani 1 1 d . . . . .
H7 H 0.5447 0.3178 0.4534 0.018 Uiso 1 1 calc R U . . .
C8 C 0.45384(12) 0.3209(3) 0.5164(2) 0.0150(5) Uani 1 1 d . . . . .
H8A H 0.4613 0.3515 0.4424 0.018 Uiso 1 1 calc R U . . .
H8B H 0.4274 0.3848 0.5466 0.018 Uiso 1 1 calc R U . . .
C9 C 0.43093(13) 0.1711(3) 0.5134(3) 0.0183(6) Uani 1 1 d . . . . .
H9A H 0.4589 0.1049 0.4935 0.022 Uiso 1 1 calc R U . . .
H9B H 0.4182 0.1457 0.5855 0.022 Uiso 1 1 calc R U . . .
C10 C 0.36934(13) 0.0130(4) 0.4249(3) 0.0221(6) Uani 1 1 d . . . . .
H10A H 0.3585 -0.0211 0.4961 0.027 Uiso 1 1 calc R U . . .
H10B H 0.3990 -0.0447 0.4006 0.027 Uiso 1 1 calc R U . . .
C11 C 0.32275(14) -0.0005(4) 0.3439(3) 0.0264(7) Uani 1 1 d . . . . .
H11A H 0.3346 0.0264 0.2715 0.032 Uiso 1 1 calc R U . . .
H11B H 0.3111 -0.0983 0.3409 0.032 Uiso 1 1 calc R U . . .
C12 C 0.29572(13) 0.2306(4) 0.3804(3) 0.0240(6) Uani 1 1 d . . . . .
H12A H 0.2657 0.2898 0.4004 0.029 Uiso 1 1 calc R U . . .
H12B H 0.3078 0.2607 0.3089 0.029 Uiso 1 1 calc R U . . .
C13 C 0.34078(13) 0.2499(4) 0.4637(3) 0.0214(6) Uani 1 1 d . . . . .
H13A H 0.3516 0.3485 0.4659 0.026 Uiso 1 1 calc R U . . .
H13B H 0.3284 0.2236 0.5359 0.026 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
Mn O1 1.873(2) 2_656 ?
Mn O1 1.873(2) . ?
Mn N1 2.043(3) 2_656 ?
Mn N1 2.043(3) . ?
Mn O1W 2.236(3) . ?
Mn Cl1 2.6038(13) . ?
N1 C7 1.296(4) . ?
N1 C8 1.479(4) . ?
N2 C13 1.465(4) . ?
N2 C10 1.470(4) . ?
N2 C9 1.473(4) . ?
O1 C1 1.321(4) . ?
O2 C12 1.422(5) . ?
O2 C11 1.430(5) . ?
O1W H11 0.68(5) . ?
O2W H21 0.84(7) . ?
O2W H22 0.87(7) . ?
C1 C2 1.412(4) . ?
C1 C6 1.414(4) . ?
C2 C3 1.390(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.401(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.416(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.439(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.527(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.524(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.521(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Mn O1 170.74(15) 2_656 . ?
O1 Mn N1 91.12(11) 2_656 2_656 ?
O1 Mn N1 89.17(11) . 2_656 ?
O1 Mn N1 89.17(11) 2_656 . ?
O1 Mn N1 91.12(11) . . ?
N1 Mn N1 176.35(14) 2_656 . ?
O1 Mn O1W 85.37(8) 2_656 . ?
O1 Mn O1W 85.37(8) . . ?
N1 Mn O1W 91.83(7) 2_656 . ?
N1 Mn O1W 91.83(7) . . ?
O1 Mn Cl1 94.63(8) 2_656 . ?
O1 Mn Cl1 94.63(8) . . ?
N1 Mn Cl1 88.17(7) 2_656 . ?
N1 Mn Cl1 88.17(7) . . ?
O1W Mn Cl1 180.0 . . ?
C7 N1 C8 115.7(3) . . ?
C7 N1 Mn 123.9(2) . . ?
C8 N1 Mn 120.5(2) . . ?
C13 N2 C10 109.6(3) . . ?
C13 N2 C9 112.5(3) . . ?
C10 N2 C9 108.9(2) . . ?
C1 O1 Mn 132.0(2) . . ?
C12 O2 C11 109.6(3) . . ?
Mn O1W H11 120(5) . . ?
H21 O2W H22 103(6) . . ?
O1 C1 C2 118.6(3) . . ?
O1 C1 C6 122.7(3) . . ?
C2 C1 C6 118.6(3) . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 121.4(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 119.0(3) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 119.7(3) . . ?
C1 C6 C7 122.9(3) . . ?
C5 C6 C7 117.3(3) . . ?
N1 C7 C6 127.0(3) . . ?
N1 C7 H7 116.5 . . ?
C6 C7 H7 116.5 . . ?
N1 C8 C9 111.7(2) . . ?
N1 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
N2 C9 C8 110.7(2) . . ?
N2 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
N2 C10 C11 110.3(3) . . ?
N2 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
N2 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
O2 C11 C10 111.4(3) . . ?
O2 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
O2 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
O2 C12 C13 111.5(3) . . ?
O2 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
O2 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
N2 C13 C12 109.7(3) . . ?
N2 C13 H13A 109.7 . . ?
C12 C13 H13A 109.7 . . ?
N2 C13 H13B 109.7 . . ?
C12 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?

_refine_diff_density_max         2.239
_refine_diff_density_min         -0.812
_refine_diff_density_rms         0.133

####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1841251'
_audit_update_record             
;
2018-07-24 deposited with the CCDC.
2018-07-27 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         'C28 H36 Mn N6 O2 S2, C N S, H2 O'
_chemical_formula_sum            'C29 H38 Mn N7 O3 S3'
_chemical_formula_weight         683.78

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'
Mn Mn 0.3368 0.7283 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   12.3979(5)
_cell_length_b                   18.3692(7)
_cell_length_c                   14.6907(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.363(2)
_cell_angle_gamma                90
_cell_volume                     3268.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    3452
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      27.64

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             1432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.28
_exptl_absorpt_coefficient_mu    0.637
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.738
_exptl_absorpt_correction_T_max  0.870
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_absorpt_special_details   
'Bruker (2009). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.'

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49725
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.664
_diffrn_reflns_theta_max         28.313
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             8104
_reflns_number_gt                6537
_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    'SHELX97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep3 for Windows (Farrugia,1997)'
_computing_publication_material  'Wingx 2013.3 (Farrugia, 1999)'

_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)+(0.0442P)²+3.0386P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8104
_refine_ls_number_parameters     394
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1277
_refine_ls_wR_factor_gt          0.1157
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
Mn Mn 0.72335(2) 0.65987(2) 0.56274(2) 0.03288(10) Uani 1 1 d . . . . .
S1 S 0.71754(8) 0.93124(4) 0.55374(7) 0.0738(3) Uani 1 1 d . . . . .
N5 N 0.71891(17) 0.78125(12) 0.57490(17) 0.0536(5) Uani 1 1 d . . . . .
C15 C 0.71894(18) 0.84341(13) 0.56571(16) 0.0427(5) Uani 1 1 d . . . . .
S2 S 0.77724(6) 0.43058(5) 0.41757(6) 0.0665(2) Uani 1 1 d . . . . .
N6 N 0.73644(18) 0.53760(12) 0.54020(17) 0.0553(5) Uani 1 1 d . . . . .
C16 C 0.75302(18) 0.49347(13) 0.48902(18) 0.0437(5) Uani 1 1 d . . . . .
N1 N 0.88939(14) 0.66667(9) 0.56373(13) 0.0358(4) Uani 1 1 d . . . . .
N2 N 0.99565(15) 0.62783(10) 0.34782(13) 0.0363(4) Uani 1 1 d . . . . .
H2N H 1.058(2) 0.6532(14) 0.3708(18) 0.044 Uiso 1 1 d . U . . .
N3 N 0.55938(14) 0.65306(9) 0.56384(12) 0.0329(4) Uani 1 1 d . . . . .
N4 N 0.44950(14) 0.63105(9) 0.78244(12) 0.0317(3) Uani 1 1 d . . . . .
H4N H 0.390(2) 0.6525(13) 0.7564(17) 0.038 Uiso 1 1 d . U . . .
O1 O 0.75480(13) 0.65047(11) 0.69283(11) 0.0504(4) Uani 1 1 d . . . . .
O2 O 0.68694(12) 0.66827(9) 0.43234(10) 0.0410(3) Uani 1 1 d . . . . .
C1 C 0.84719(17) 0.63245(12) 0.75141(15) 0.0381(4) Uani 1 1 d . . . . .
C2 C 0.8436(2) 0.61434(16) 0.84350(17) 0.0535(6) Uani 1 1 d . . . . .
H2 H 0.7760 0.6137 0.8613 0.064 Uiso 1 1 calc R U . . .
C3 C 0.9377(2) 0.59758(18) 0.90759(18) 0.0596(7) Uani 1 1 d . . . . .
H3 H 0.9330 0.5862 0.9683 0.072 Uiso 1 1 calc R U . . .
C4 C 1.0402(2) 0.59718(18) 0.88381(19) 0.0611(7) Uani 1 1 d . . . . .
H4 H 1.1034 0.5845 0.9275 0.073 Uiso 1 1 calc R U . . .
C5 C 1.0465(2) 0.61580(15) 0.79493(19) 0.0527(6) Uani 1 1 d . . . . .
H5 H 1.1151 0.6169 0.7790 0.063 Uiso 1 1 calc R U . . .
C6 C 0.95089(17) 0.63342(12) 0.72670(16) 0.0384(4) Uani 1 1 d . . . . .
C7 C 0.96576(17) 0.65383(12) 0.63610(16) 0.0400(5) Uani 1 1 d . . . . .
H7 H 1.0382 0.6583 0.6289 0.048 Uiso 1 1 calc R U . . .
C8 C 0.92646(18) 0.68550(12) 0.47760(16) 0.0401(5) Uani 1 1 d . . . . .
H8A H 0.9965 0.7110 0.4929 0.048 Uiso 1 1 calc R U . . .
H8B H 0.8728 0.7171 0.4389 0.048 Uiso 1 1 calc R U . . .
C9 C 0.93892(19) 0.61563(12) 0.42573(16) 0.0408(5) Uani 1 1 d . . . . .
H9A H 0.9807 0.5807 0.4689 0.049 Uiso 1 1 calc R U . . .
H9B H 0.8664 0.5951 0.4013 0.049 Uiso 1 1 calc R U . . .
C10 C 0.9345(2) 0.67247(17) 0.26926(19) 0.0574(7) Uani 1 1 d . . . . .
H10A H 0.9373 0.7237 0.2858 0.069 Uiso 1 1 calc R U . . .
H10B H 0.8579 0.6574 0.2518 0.069 Uiso 1 1 calc R U . . .
C11 C 0.9934(2) 0.65863(18) 0.19097(19) 0.0601(7) Uani 1 1 d . . . . .
H11A H 1.0472 0.6966 0.1888 0.072 Uiso 1 1 calc R U . . .
H11B H 0.9411 0.6572 0.1315 0.072 Uiso 1 1 calc R U . . .
C12 C 1.0500(3) 0.58556(18) 0.2121(2) 0.0730(9) Uani 1 1 d . . . . .
H12A H 1.0234 0.5514 0.1620 0.088 Uiso 1 1 calc R U . . .
H12B H 1.1293 0.5907 0.2196 0.088 Uiso 1 1 calc R U . . .
C13 C 1.0219(3) 0.55929(14) 0.3018(2) 0.0569(7) Uani 1 1 d . . . . .
H13A H 0.9588 0.5268 0.2893 0.068 Uiso 1 1 calc R U . . .
H13B H 1.0841 0.5342 0.3404 0.068 Uiso 1 1 calc R U . . .
C21 C 0.60146(17) 0.63964(11) 0.37375(14) 0.0339(4) Uani 1 1 d . . . . .
C22 C 0.6042(2) 0.63494(14) 0.27926(16) 0.0450(5) Uani 1 1 d . . . . .
H15 H 0.6674 0.6493 0.2596 0.054 Uiso 1 1 calc R U . . .
C23 C 0.5155(2) 0.60959(14) 0.21552(17) 0.0489(6) Uani 1 1 d . . . . .
H16 H 0.5191 0.6078 0.1530 0.059 Uiso 1 1 calc R U . . .
C24 C 0.4197(2) 0.58641(15) 0.24164(18) 0.0517(6) Uani 1 1 d . . . . .
H17 H 0.3606 0.5683 0.1976 0.062 Uiso 1 1 calc R U . . .
C25 C 0.4143(2) 0.59085(14) 0.33368(17) 0.0475(5) Uani 1 1 d . . . . .
H18 H 0.3506 0.5757 0.3520 0.057 Uiso 1 1 calc R U . . .
C26 C 0.50390(17) 0.61799(12) 0.40118(15) 0.0363(4) Uani 1 1 d . . . . .
C27 C 0.48611(17) 0.63192(12) 0.49321(15) 0.0378(4) Uani 1 1 d . . . . .
H20 H 0.4149 0.6250 0.5024 0.045 Uiso 1 1 calc R U . . .
C28 C 0.51934(18) 0.67527(12) 0.64749(15) 0.0370(4) Uani 1 1 d . . . . .
H21A H 0.4482 0.6990 0.6286 0.044 Uiso 1 1 calc R U . . .
H21B H 0.5706 0.7099 0.6832 0.044 Uiso 1 1 calc R U . . .
C29 C 0.50829(18) 0.60979(11) 0.70790(15) 0.0358(4) Uani 1 1 d . . . . .
H22A H 0.4674 0.5716 0.6698 0.043 Uiso 1 1 calc R U . . .
H22B H 0.5810 0.5911 0.7359 0.043 Uiso 1 1 calc R U . . .
C30 C 0.4226(2) 0.56913(13) 0.83982(17) 0.0509(6) Uani 1 1 d . . . . .
H23A H 0.4859 0.5373 0.8587 0.061 Uiso 1 1 calc R U . . .
H23B H 0.3611 0.5409 0.8053 0.061 Uiso 1 1 calc R U . . .
C31 C 0.3928(3) 0.60514(15) 0.92316(19) 0.0611(7) Uani 1 1 d . . . . .
H24A H 0.4181 0.5760 0.9787 0.073 Uiso 1 1 calc R U . . .
H24B H 0.3134 0.6111 0.9136 0.073 Uiso 1 1 calc R U . . .
C32 C 0.4499(2) 0.67886(14) 0.93312(16) 0.0451(5) Uani 1 1 d . . . . .
H25A H 0.3964 0.7178 0.9301 0.054 Uiso 1 1 calc R U . . .
H25B H 0.5028 0.6820 0.9921 0.054 Uiso 1 1 calc R U . . .
C33 C 0.5082(2) 0.68436(14) 0.85240(17) 0.0473(6) Uani 1 1 d . . . . .
H26A H 0.5024 0.7332 0.8268 0.057 Uiso 1 1 calc R U . . .
H26B H 0.5857 0.6718 0.8722 0.057 Uiso 1 1 calc R U . . .
S3 S 0.21971(8) 0.80350(5) 0.56556(5) 0.0754(3) Uani 1 1 d . . . . .
N7 N 0.25928(19) 0.72327(13) 0.72907(16) 0.0543(5) Uani 1 1 d . . . . .
C17 C 0.24503(19) 0.75567(14) 0.66122(18) 0.0463(5) Uani 1 1 d . . . . .
O1W O 0.19538(19) 0.69820(14) 0.38595(15) 0.0753(7) Uani 1 1 d . . . . .
H1A H 0.2003 0.7237 0.4350 0.113 Uiso 1 1 d . U . . .
H1B H 0.2105 0.7246 0.3427 0.113 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn O1 1.8748(16) . ?
Mn O2 1.8781(15) . ?
Mn N3 2.0403(17) . ?
Mn N1 2.0593(17) . ?
Mn N5 2.238(2) . ?
Mn N6 2.281(2) . ?
S1 C15 1.623(3) . ?
N5 C15 1.150(3) . ?
S2 C16 1.631(3) . ?
N6 C16 1.154(3) . ?
N1 C7 1.285(3) . ?
N1 C8 1.477(3) . ?
N2 C9 1.483(3) . ?
N2 C10 1.485(3) . ?
N2 C13 1.498(3) . ?
N2 H2N 0.90(3) . ?
N3 C27 1.284(3) . ?
N3 C28 1.478(2) . ?
N4 C33 1.491(3) . ?
N4 C29 1.492(2) . ?
N4 C30 1.495(3) . ?
N4 H4N 0.86(3) . ?
O1 C1 1.319(3) . ?
O2 C21 1.323(3) . ?
C1 C2 1.403(3) . ?
C1 C6 1.409(3) . ?
C2 C3 1.369(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.416(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.432(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.517(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.510(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.516(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.512(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C21 C22 1.398(3) . ?
C21 C26 1.411(3) . ?
C22 C23 1.365(4) . ?
C22 H15 0.9300 . ?
C23 C24 1.390(4) . ?
C23 H16 0.9300 . ?
C24 C25 1.370(3) . ?
C24 H17 0.9300 . ?
C25 C26 1.412(3) . ?
C25 H18 0.9300 . ?
C26 C27 1.439(3) . ?
C27 H20 0.9300 . ?
C28 C29 1.518(3) . ?
C28 H21A 0.9700 . ?
C28 H21B 0.9700 . ?
C29 H22A 0.9700 . ?
C29 H22B 0.9700 . ?
C30 C31 1.506(3) . ?
C30 H23A 0.9700 . ?
C30 H23B 0.9700 . ?
C31 C32 1.521(4) . ?
C31 H24A 0.9700 . ?
C31 H24B 0.9700 . ?
C32 C33 1.518(3) . ?
C32 H25A 0.9700 . ?
C32 H25B 0.9700 . ?
C33 H26A 0.9700 . ?
C33 H26B 0.9700 . ?
S3 C17 1.630(3) . ?
N7 C17 1.142(3) . ?
O1W H1A 0.8501 . ?
O1W H1B 0.8512 . ?

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 Mn O2 178.06(7) . . ?
O1 Mn N3 88.65(7) . . ?
O2 Mn N3 89.47(7) . . ?
O1 Mn N1 90.52(7) . . ?
O2 Mn N1 91.36(7) . . ?
N3 Mn N1 179.16(7) . . ?
O1 Mn N5 90.78(9) . . ?
O2 Mn N5 89.71(8) . . ?
N3 Mn N5 91.08(7) . . ?
N1 Mn N5 88.89(7) . . ?
O1 Mn N6 92.96(9) . . ?
O2 Mn N6 86.67(8) . . ?
N3 Mn N6 92.45(7) . . ?
N1 Mn N6 87.63(7) . . ?
N5 Mn N6 174.92(8) . . ?
C15 N5 Mn 168.3(2) . . ?
N5 C15 S1 179.1(2) . . ?
C16 N6 Mn 144.6(2) . . ?
N6 C16 S2 179.4(3) . . ?
C7 N1 C8 116.27(18) . . ?
C7 N1 Mn 123.57(15) . . ?
C8 N1 Mn 120.14(14) . . ?
C9 N2 C10 115.84(18) . . ?
C9 N2 C13 113.97(18) . . ?
C10 N2 C13 103.7(2) . . ?
C9 N2 H2N 107.3(17) . . ?
C10 N2 H2N 105.0(16) . . ?
C13 N2 H2N 110.6(17) . . ?
C27 N3 C28 116.74(17) . . ?
C27 N3 Mn 123.08(14) . . ?
C28 N3 Mn 120.15(14) . . ?
C33 N4 C29 115.77(16) . . ?
C33 N4 C30 104.22(18) . . ?
C29 N4 C30 114.68(17) . . ?
C33 N4 H4N 104.8(16) . . ?
C29 N4 H4N 107.8(17) . . ?
C30 N4 H4N 109.0(17) . . ?
C1 O1 Mn 130.56(14) . . ?
C21 O2 Mn 127.96(13) . . ?
O1 C1 C2 119.1(2) . . ?
O1 C1 C6 122.8(2) . . ?
C2 C1 C6 118.1(2) . . ?
C3 C2 C1 121.2(2) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 121.3(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 118.8(2) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.5(2) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 119.1(2) . . ?
C1 C6 C7 123.3(2) . . ?
C5 C6 C7 117.6(2) . . ?
N1 C7 C6 126.75(19) . . ?
N1 C7 H7 116.6 . . ?
C6 C7 H7 116.6 . . ?
N1 C8 C9 108.42(17) . . ?
N1 C8 H8A 110.0 . . ?
C9 C8 H8A 110.0 . . ?
N1 C8 H8B 110.0 . . ?
C9 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
N2 C9 C8 112.08(17) . . ?
N2 C9 H9A 109.2 . . ?
C8 C9 H9A 109.2 . . ?
N2 C9 H9B 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
N2 C10 C11 104.5(2) . . ?
N2 C10 H10A 110.9 . . ?
C11 C10 H10A 110.9 . . ?
N2 C10 H10B 110.9 . . ?
C11 C10 H10B 110.9 . . ?
H10A C10 H10B 108.9 . . ?
C10 C11 C12 105.7(2) . . ?
C10 C11 H11A 110.6 . . ?
C12 C11 H11A 110.6 . . ?
C10 C11 H11B 110.6 . . ?
C12 C11 H11B 110.6 . . ?
H11A C11 H11B 108.7 . . ?
C13 C12 C11 106.2(2) . . ?
C13 C12 H12A 110.5 . . ?
C11 C12 H12A 110.5 . . ?
C13 C12 H12B 110.5 . . ?
C11 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
N2 C13 C12 103.8(2) . . ?
N2 C13 H13A 111.0 . . ?
C12 C13 H13A 111.0 . . ?
N2 C13 H13B 111.0 . . ?
C12 C13 H13B 111.0 . . ?
H13A C13 H13B 109.0 . . ?
O2 C21 C22 118.95(19) . . ?
O2 C21 C26 122.85(18) . . ?
C22 C21 C26 118.1(2) . . ?
C23 C22 C21 121.0(2) . . ?
C23 C22 H15 119.5 . . ?
C21 C22 H15 119.5 . . ?
C22 C23 C24 121.7(2) . . ?
C22 C23 H16 119.1 . . ?
C24 C23 H16 119.1 . . ?
C25 C24 C23 118.6(2) . . ?
C25 C24 H17 120.7 . . ?
C23 C24 H17 120.7 . . ?
C24 C25 C26 121.1(2) . . ?
C24 C25 H18 119.4 . . ?
C26 C25 H18 119.4 . . ?
C21 C26 C25 119.5(2) . . ?
C21 C26 C27 122.1(2) . . ?
C25 C26 C27 117.83(19) . . ?
N3 C27 C26 126.07(19) . . ?
N3 C27 H20 117.0 . . ?
C26 C27 H20 117.0 . . ?
N3 C28 C29 110.84(17) . . ?
N3 C28 H21A 109.5 . . ?
C29 C28 H21A 109.5 . . ?
N3 C28 H21B 109.5 . . ?
C29 C28 H21B 109.5 . . ?
H21A C28 H21B 108.1 . . ?
N4 C29 C28 109.94(16) . . ?
N4 C29 H22A 109.7 . . ?
C28 C29 H22A 109.7 . . ?
N4 C29 H22B 109.7 . . ?
C28 C29 H22B 109.7 . . ?
H22A C29 H22B 108.2 . . ?
N4 C30 C31 104.32(19) . . ?
N4 C30 H23A 110.9 . . ?
C31 C30 H23A 110.9 . . ?
N4 C30 H23B 110.9 . . ?
C31 C30 H23B 110.9 . . ?
H23A C30 H23B 108.9 . . ?
C30 C31 C32 106.19(19) . . ?
C30 C31 H24A 110.5 . . ?
C32 C31 H24A 110.5 . . ?
C30 C31 H24B 110.5 . . ?
C32 C31 H24B 110.5 . . ?
H24A C31 H24B 108.7 . . ?
C33 C32 C31 105.89(19) . . ?
C33 C32 H25A 110.6 . . ?
C31 C32 H25A 110.6 . . ?
C33 C32 H25B 110.6 . . ?
C31 C32 H25B 110.6 . . ?
H25A C32 H25B 108.7 . . ?
N4 C33 C32 104.54(17) . . ?
N4 C33 H26A 110.8 . . ?
C32 C33 H26A 110.8 . . ?
N4 C33 H26B 110.8 . . ?
C32 C33 H26B 110.8 . . ?
H26A C33 H26B 108.9 . . ?
N7 C17 S3 177.4(2) . . ?
H1A O1W H1B 109.3 . . ?

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
C7 H7 S2 0.93 3.01 3.776(2) 141.2 3_766
C29 H22B O1 0.97 2.61 3.200(3) 119.3 .
O1W H1A S3 0.85 2.39 3.233(2) 175.0 .
O1W H1B N7 0.85 2.12 2.967(3) 171.6 4_575

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.560
_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_5
_database_code_depnum_ccdc_archive 'CCDC 1841250'
_audit_update_record             
;
2018-07-24 deposited with the CCDC.
2018-07-27 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         'C30 H40 Mn N6 O2 S3, C S N, H2 O'
_chemical_formula_sum            'C31 H42 Mn N7 O3 S3'
_chemical_formula_weight         711.83

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'I a'
_space_group_name_Hall           'I -2ya'

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

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

_cell_length_a                   12.4782(18)
_cell_length_b                   19.001(3)
_cell_length_c                   14.782(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.092(11)
_cell_angle_gamma                90
_cell_volume                     3460.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2286
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      21.21

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_F_000             1496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.605
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.785
_exptl_absorpt_correction_T_max  0.870
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_absorpt_special_details   
'Bruker (2009). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.'

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48619
_diffrn_reflns_av_unetI/netI     0.0944
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.791
_diffrn_reflns_theta_max         23.248
_diffrn_reflns_theta_full        23.248
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             28315
_reflns_number_gt                17560
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.985
_reflns_Friedel_fraction_max     0.981
_reflns_Friedel_fraction_full    0.981

_reflns_special_details          
;
 _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    'SHELX97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep3 for Windows (Farrugia,1997)'
_computing_publication_material  'Wingx 2013.3 (Farrugia, 1999)'

_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)+(0.0410P)²+22.7900P] 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_abs_structure_details 
;
 Flack x determined using 1191 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.49(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         28315
_refine_ls_number_parameters     407
_refine_ls_number_restraints     63
_refine_ls_R_factor_all          0.1261
_refine_ls_R_factor_gt           0.0722
_refine_ls_wR_factor_ref         0.2104
_refine_ls_wR_factor_gt          0.1793
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.035
_refine_ls_shift/su_mean         0.008

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
Mn Mn 0.6137(8) 0.17780(9) 0.5022(5) 0.0592(7) Uani 1 1 d . . . . .
S1 S 0.6177(17) -0.0828(2) 0.4993(14) 0.140(3) Uani 1 1 d . . . . .
S2 S 0.6144(18) 0.44008(19) 0.5004(14) 0.0958(15) Uani 1 1 d . . . . .
N1 N 0.777(2) 0.1748(11) 0.4984(13) 0.044(7) Uani 1 1 d . . . . .
N2 N 0.893(2) 0.1152(13) 0.2885(14) 0.064(9) Uani 1 1 d . . . . .
H2N H 0.9562 0.1457 0.3060 0.077 Uiso 1 1 calc R U . . .
N3 N 0.448(2) 0.1727(13) 0.5072(17) 0.068(9) Uani 1 1 d . . . . .
N4 N 0.335(2) 0.1159(11) 0.7173(15) 0.062(8) Uani 1 1 d . . . . .
H4N H 0.2726 0.1476 0.7004 0.075 Uiso 1 1 calc R U . . .
N5 N 0.615(4) 0.0603(7) 0.506(3) 0.077(4) Uani 1 1 d . . . . .
N6 N 0.607(4) 0.2927(6) 0.501(3) 0.078(4) Uani 1 1 d . U . . .
O1 O 0.6419(18) 0.1783(12) 0.6306(13) 0.068(7) Uani 1 1 d . . . . .
O2 O 0.588(2) 0.1779(12) 0.3735(13) 0.078(8) Uani 1 1 d . . . . .
C1 C 0.731(3) 0.1593(16) 0.6846(16) 0.058(9) Uani 1 1 d . U . . .
C2 C 0.727(3) 0.1482(19) 0.7821(19) 0.070(10) Uani 1 1 d . . . . .
H2 H 0.6605 0.1536 0.8026 0.084 Uiso 1 1 calc R U . . .
C3 C 0.814(4) 0.130(2) 0.844(2) 0.086(12) Uani 1 1 d . . . . .
H3 H 0.8078 0.1247 0.9050 0.103 Uiso 1 1 calc R U . . .
C4 C 0.913(3) 0.121(2) 0.814(2) 0.102(16) Uani 1 1 d . . . . .
H4 H 0.9731 0.1070 0.8564 0.123 Uiso 1 1 calc R U . . .
C5 C 0.924(3) 0.131(2) 0.725(2) 0.087(13) Uani 1 1 d . . . . .
H5 H 0.9913 0.1257 0.7059 0.104 Uiso 1 1 calc R U . . .
C6 C 0.834(3) 0.1495(18) 0.6628(17) 0.061(10) Uani 1 1 d . . . . .
C7 C 0.850(3) 0.1605(16) 0.571(2) 0.060(9) Uani 1 1 d . . . . .
H7 H 0.9213 0.1573 0.5601 0.071 Uiso 1 1 calc R U . . .
C8 C 0.818(3) 0.1827(12) 0.4088(18) 0.085(13) Uani 1 1 d . . . . .
H8A H 0.8859 0.2081 0.4178 0.102 Uiso 1 1 calc R U . . .
H8B H 0.7655 0.2094 0.3665 0.102 Uiso 1 1 calc R U . . .
C9 C 0.834(3) 0.1087(16) 0.3683(19) 0.072(10) Uani 1 1 d . U . . .
H9A H 0.8749 0.0791 0.4149 0.087 Uiso 1 1 calc R U . . .
H9B H 0.7637 0.0867 0.3489 0.087 Uiso 1 1 calc R U . . .
C10 C 0.932(4) 0.0442(17) 0.265(2) 0.088(13) Uani 1 1 d . . . . .
H10A H 0.8697 0.0135 0.2474 0.106 Uiso 1 1 calc R U . . .
H10B H 0.9761 0.0239 0.3185 0.106 Uiso 1 1 calc R U . . .
C11 C 1.000(4) 0.0494(19) 0.184(2) 0.098(13) Uani 1 1 d . . . . .
H11A H 1.0655 0.0760 0.2041 0.118 Uiso 1 1 calc R U . . .
H11B H 1.0204 0.0025 0.1674 0.118 Uiso 1 1 calc R U . . .
C12 C 0.937(4) 0.084(2) 0.104(2) 0.091(13) Uani 1 1 d . . . . .
H12A H 0.8801 0.0520 0.0762 0.109 Uiso 1 1 calc R U . . .
H12B H 0.9845 0.0923 0.0588 0.109 Uiso 1 1 calc R U . . .
C13 C 0.887(3) 0.151(2) 0.125(2) 0.099(13) Uani 1 1 d . U . . .
H13A H 0.8399 0.1668 0.0702 0.119 Uiso 1 1 calc R U . . .
H13B H 0.9444 0.1856 0.1392 0.119 Uiso 1 1 calc R U . . .
C14 C 0.820(3) 0.1481(18) 0.2059(16) 0.087(12) Uani 1 1 d . . . . .
H14A H 0.7987 0.1952 0.2209 0.105 Uiso 1 1 calc R U . . .
H14B H 0.7554 0.1200 0.1889 0.105 Uiso 1 1 calc R U . . .
C15 C 0.617(3) -0.0005(7) 0.505(3) 0.048(4) Uani 1 1 d . . . . .
C16 C 0.607(4) 0.3558(8) 0.498(3) 0.059(5) Uani 1 1 d . . . . .
C21 C 0.498(3) 0.1603(17) 0.314(2) 0.060(9) Uani 1 1 d . U . . .
C22 C 0.512(3) 0.1548(19) 0.2235(19) 0.071(10) Uani 1 1 d . U . . .
H22 H 0.5784 0.1633 0.2048 0.085 Uiso 1 1 calc R U . . .
C23 C 0.422(3) 0.136(2) 0.164(2) 0.078(11) Uani 1 1 d . U . . .
H23 H 0.4301 0.1313 0.1024 0.093 Uiso 1 1 calc R U . . .
C24 C 0.319(3) 0.1246(19) 0.187(2) 0.081(11) Uani 1 1 d . U . . .
H24 H 0.2599 0.1122 0.1435 0.097 Uiso 1 1 calc R U . . .
C25 C 0.311(3) 0.132(2) 0.277(2) 0.075(11) Uani 1 1 d . U . . .
H25 H 0.2440 0.1252 0.2956 0.090 Uiso 1 1 calc R U . . .
C26 C 0.402(3) 0.1506(19) 0.3461(18) 0.060(9) Uani 1 1 d . U . . .
C27 C 0.377(3) 0.1619(18) 0.4397(18) 0.074(11) Uani 1 1 d . . . . .
H27 H 0.3048 0.1608 0.4484 0.089 Uiso 1 1 calc R U . . .
C28 C 0.406(2) 0.1834(15) 0.5924(15) 0.053(8) Uani 1 1 d . . . . .
H28A H 0.3359 0.2065 0.5803 0.064 Uiso 1 1 calc R U . . .
H28B H 0.4552 0.2130 0.6332 0.064 Uiso 1 1 calc R U . . .
C29 C 0.395(3) 0.1138(15) 0.6355(18) 0.064(9) Uani 1 1 d . . . . .
H29A H 0.4672 0.0947 0.6554 0.077 Uiso 1 1 calc R U . . .
H29B H 0.3575 0.0821 0.5898 0.077 Uiso 1 1 calc R U . . .
C30 C 0.289(3) 0.0465(17) 0.738(2) 0.079(11) Uani 1 1 d . . . . .
H30A H 0.2428 0.0290 0.6835 0.094 Uiso 1 1 calc R U . . .
H30B H 0.3479 0.0131 0.7540 0.094 Uiso 1 1 calc R U . . .
C31 C 0.227(3) 0.0520(17) 0.813(2) 0.074(11) Uani 1 1 d . . . . .
H31A H 0.1963 0.0064 0.8239 0.089 Uiso 1 1 calc R U . . .
H31B H 0.1669 0.0846 0.7960 0.089 Uiso 1 1 calc R U . . .
C32 C 0.300(4) 0.078(2) 0.902(2) 0.106(15) Uani 1 1 d . . . . .
H32A H 0.3624 0.0478 0.9184 0.128 Uiso 1 1 calc R U . . .
H32B H 0.2597 0.0804 0.9529 0.128 Uiso 1 1 calc R U . . .
C33 C 0.337(4) 0.154(2) 0.8765(18) 0.112(16) Uani 1 1 d . . . . .
H33A H 0.2738 0.1839 0.8578 0.134 Uiso 1 1 calc R U . . .
H33B H 0.3813 0.1759 0.9289 0.134 Uiso 1 1 calc R U . . .
C34 C 0.400(3) 0.146(2) 0.800(2) 0.099(14) Uani 1 1 d . . . . .
H34A H 0.4274 0.1916 0.7849 0.119 Uiso 1 1 calc R U . . .
H34B H 0.4618 0.1156 0.8194 0.119 Uiso 1 1 calc R U . . .
S3 S 0.115(2) 0.2116(2) 1.0010(11) 0.132(2) Uani 1 1 d . . . . .
C17 C 0.1213(16) 0.2521(8) 1.1086(11) 0.060(5) Uani 1 1 d D . . . .
N7 N 0.164(2) 0.2923(14) 1.1805(15) 0.078(9) Uani 1 1 d D . . . .
O1W O 0.069(2) 0.2861(13) 0.8215(16) 0.113(10) Uani 1 1 d . . . . .
H1W H 0.1301 0.2754 0.7987 0.169 Uiso 1 1 d . U . . .
H2W H 0.0880 0.3214 0.8556 0.169 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn O1 1.87(2) . ?
Mn O2 1.88(2) . ?
Mn N1 2.05(3) . ?
Mn N3 2.08(3) . ?
Mn N6 2.185(13) . ?
Mn N5 2.233(13) . ?
S1 C15 1.565(15) . ?
S2 C16 1.604(16) . ?
N1 C7 1.32(4) . ?
N1 C8 1.50(3) . ?
N2 C9 1.49(4) . ?
N2 C10 1.49(4) . ?
N2 C14 1.53(3) . ?
N2 H2N 0.9800 . ?
N3 C27 1.24(4) . ?
N3 C28 1.45(3) . ?
N4 C34 1.47(4) . ?
N4 C30 1.49(4) . ?
N4 C29 1.52(3) . ?
N4 H4N 0.9800 . ?
N5 C15 1.156(16) . ?
N6 C16 1.200(16) . ?
O1 C1 1.31(4) . ?
O2 C21 1.36(4) . ?
C1 C6 1.40(5) . ?
C1 C2 1.46(4) . ?
C2 C3 1.35(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.39(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.37(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.37(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.42(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.55(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.58(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.47(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.47(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.57(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C21 C26 1.37(4) . ?
C21 C22 1.38(4) . ?
C22 C23 1.35(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.40(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.36(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.44(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.48(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.48(4) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.46(4) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C32 1.57(5) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.58(5) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.49(5) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
S3 C17 1.76(2) . ?
C17 N7 1.35(3) . ?
O1W H1W 0.9046 . ?
O1W H2W 0.8497 . ?

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 Mn O2 178.9(15) . . ?
O1 Mn N1 90.0(10) . . ?
O2 Mn N1 89.0(10) . . ?
O1 Mn N3 89.6(10) . . ?
O2 Mn N3 91.4(12) . . ?
N1 Mn N3 175.7(4) . . ?
O1 Mn N6 90.3(12) . . ?
O2 Mn N6 89.4(13) . . ?
N1 Mn N6 93.9(14) . . ?
N3 Mn N6 90.4(14) . . ?
O1 Mn N5 89.0(14) . . ?
O2 Mn N5 91.4(14) . . ?
N1 Mn N5 88.1(13) . . ?
N3 Mn N5 87.6(13) . . ?
N6 Mn N5 177.9(18) . . ?
C7 N1 C8 117(3) . . ?
C7 N1 Mn 123.0(19) . . ?
C8 N1 Mn 120(2) . . ?
C9 N2 C10 109(2) . . ?
C9 N2 C14 111(3) . . ?
C10 N2 C14 111(2) . . ?
C9 N2 H2N 108.7 . . ?
C10 N2 H2N 108.6 . . ?
C14 N2 H2N 108.6 . . ?
C27 N3 C28 114(3) . . ?
C27 N3 Mn 124(2) . . ?
C28 N3 Mn 121(2) . . ?
C34 N4 C30 111(2) . . ?
C34 N4 C29 113(3) . . ?
C30 N4 C29 113(2) . . ?
C34 N4 H4N 106.7 . . ?
C30 N4 H4N 106.6 . . ?
C29 N4 H4N 106.5 . . ?
C15 N5 Mn 178(4) . . ?
C16 N6 Mn 177(4) . . ?
C1 O1 Mn 128(2) . . ?
C21 O2 Mn 130(2) . . ?
O1 C1 C6 128(2) . . ?
O1 C1 C2 119(3) . . ?
C6 C1 C2 113(3) . . ?
C3 C2 C1 123(3) . . ?
C3 C2 H2 118.2 . . ?
C1 C2 H2 118.4 . . ?
C2 C3 C4 119(3) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 121(4) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 119(4) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 125(3) . . ?
C5 C6 C7 117(3) . . ?
C1 C6 C7 118(3) . . ?
N1 C7 C6 129(3) . . ?
N1 C7 H7 115.7 . . ?
C6 C7 H7 115.4 . . ?
N1 C8 C9 109(2) . . ?
N1 C8 H8A 109.6 . . ?
C9 C8 H8A 109.7 . . ?
N1 C8 H8B 109.9 . . ?
C9 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
N2 C9 C8 110(3) . . ?
N2 C9 H9A 109.6 . . ?
C8 C9 H9A 109.8 . . ?
N2 C9 H9B 109.8 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.2 . . ?
N2 C10 C11 111(3) . . ?
N2 C10 H10A 109.5 . . ?
C11 C10 H10A 109.4 . . ?
N2 C10 H10B 109.5 . . ?
C11 C10 H10B 109.7 . . ?
H10A C10 H10B 108.1 . . ?
C12 C11 C10 111(3) . . ?
C12 C11 H11A 109.6 . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11B 109.5 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C13 114(3) . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12A 108.7 . . ?
C11 C12 H12B 108.5 . . ?
C13 C12 H12B 109.0 . . ?
H12A C12 H12B 107.7 . . ?
C12 C13 C14 115(3) . . ?
C12 C13 H13A 108.6 . . ?
C14 C13 H13A 108.7 . . ?
C12 C13 H13B 108.4 . . ?
C14 C13 H13B 108.1 . . ?
H13A C13 H13B 107.5 . . ?
N2 C14 C13 108(3) . . ?
N2 C14 H14A 110.4 . . ?
C13 C14 H14A 110.5 . . ?
N2 C14 H14B 110.1 . . ?
C13 C14 H14B 109.8 . . ?
H14A C14 H14B 108.5 . . ?
N5 C15 S1 178(4) . . ?
N6 C16 S2 176(5) . . ?
O2 C21 C26 119(3) . . ?
O2 C21 C22 115(3) . . ?
C26 C21 C22 125(3) . . ?
C23 C22 C21 116(4) . . ?
C23 C22 H22 122.1 . . ?
C21 C22 H22 122.1 . . ?
C22 C23 C24 125(3) . . ?
C22 C23 H23 117.2 . . ?
C24 C23 H23 117.8 . . ?
C25 C24 C23 116(4) . . ?
C25 C24 H24 122.0 . . ?
C23 C24 H24 122.2 . . ?
C24 C25 C26 123(3) . . ?
C24 C25 H25 118.4 . . ?
C26 C25 H25 118.4 . . ?
C21 C26 C25 115(3) . . ?
C21 C26 C27 129(3) . . ?
C25 C26 C27 116(3) . . ?
N3 C27 C26 123(4) . . ?
N3 C27 H27 118.3 . . ?
C26 C27 H27 118.5 . . ?
N3 C28 C29 109(2) . . ?
N3 C28 H28A 110.1 . . ?
C29 C28 H28A 110.1 . . ?
N3 C28 H28B 109.9 . . ?
C29 C28 H28B 109.9 . . ?
H28A C28 H28B 108.3 . . ?
C28 C29 N4 114(2) . . ?
C28 C29 H29A 108.8 . . ?
N4 C29 H29A 108.6 . . ?
C28 C29 H29B 108.7 . . ?
N4 C29 H29B 108.8 . . ?
H29A C29 H29B 107.6 . . ?
C31 C30 N4 111(3) . . ?
C31 C30 H30A 109.4 . . ?
N4 C30 H30A 109.5 . . ?
C31 C30 H30B 109.5 . . ?
N4 C30 H30B 109.4 . . ?
H30A C30 H30B 108.0 . . ?
C30 C31 C32 111(3) . . ?
C30 C31 H31A 109.6 . . ?
C32 C31 H31A 109.5 . . ?
C30 C31 H31B 109.7 . . ?
C32 C31 H31B 109.4 . . ?
H31A C31 H31B 108.1 . . ?
C31 C32 C33 104(2) . . ?
C31 C32 H32A 110.7 . . ?
C33 C32 H32A 111.0 . . ?
C31 C32 H32B 111.2 . . ?
C33 C32 H32B 110.8 . . ?
H32A C32 H32B 108.9 . . ?
C34 C33 C32 107(3) . . ?
C34 C33 H33A 110.6 . . ?
C32 C33 H33A 110.3 . . ?
C34 C33 H33B 110.1 . . ?
C32 C33 H33B 110.2 . . ?
H33A C33 H33B 108.5 . . ?
N4 C34 C33 112(3) . . ?
N4 C34 H34A 108.9 . . ?
C33 C34 H34A 108.8 . . ?
N4 C34 H34B 109.2 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 107.8 . . ?
N7 C17 S3 156.5(19) . . ?
H1W O1W H2W 102.9 . . ?

_refine_diff_density_max         1.104
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.107

####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1841252'
_audit_update_record             
;
2018-07-24 deposited with the CCDC.
2018-07-27 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_THETM01_7                   
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
            Calculated sin(theta_max)/wavelength =    0.5505
RESPONSE: The crystal was low diffracting
;
_vrf_PLAT023_7                   
;
PROBLEM: Resolution (too) Low [sin(theta)/Lambda < 0.6]..      23.03 Degree
RESPONSE: The crystal was low diffracting
;
_vrf_PLAT420_7                   
;
PROBLEM:  D-H Without Acceptor       O2W      --H12D           Please Check
RESPONSE: Water molecule OW2 is at 3.2 ang from a symmetry related one. 
         It is likely that respective H atoms are disordered.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H36 Mn N5 O5 S, H2 O'
_chemical_formula_sum            'C27 H38 Mn N5 O6 S'
_chemical_formula_weight         615.62

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/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                   13.9084(9)
_cell_length_b                   17.6216(11)
_cell_length_c                   12.8571(8)
_cell_angle_alpha                90
_cell_angle_beta                 111.6890(10)
_cell_angle_gamma                90
_cell_volume                     2928.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    3409
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      22.69

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.803
_exptl_absorpt_correction_T_max  0.863
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_absorpt_special_details   
'Bruker (2009). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.'

_diffrn_ambient_temperature      299(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 CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            59460
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_av_R_equivalents  0.0845
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.177
_diffrn_reflns_theta_max         23.031
_diffrn_reflns_theta_full        23.031
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4081
_reflns_number_gt                3329
_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    'SHELX97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep3 for Windows (Farrugia,1997)'
_computing_publication_material  'Wingx 2013.3 (Farrugia, 1999)'

_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)+(0.0302P)²+1.8121P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00090(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4081
_refine_ls_number_parameters     375
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0865
_refine_ls_wR_factor_gt          0.0795
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      7.892
_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
Mn Mn 0.29230(3) 0.64244(2) 0.50687(3) 0.03051(14) Uani 1 1 d . . . . .
O1 O 0.43523(13) 0.63801(11) 0.58099(15) 0.0460(5) Uani 1 1 d . . . . .
O2 O 0.14873(13) 0.64131(11) 0.43097(14) 0.0410(5) Uani 1 1 d . . . . .
O3 O -0.13971(17) 0.71048(14) 0.7612(2) 0.0726(7) Uani 1 1 d . . . . .
O4 O 0.67769(17) 0.62844(12) 0.19803(19) 0.0594(6) Uani 1 1 d . . . . .
N1 N 0.27164(15) 0.63611(12) 0.65589(18) 0.0353(5) Uani 1 1 d . . . . .
N2 N 0.31129(15) 0.63527(11) 0.35668(17) 0.0296(5) Uani 1 1 d . . . . .
N3 N 0.00887(15) 0.67230(12) 0.66556(17) 0.0356(5) Uani 1 1 d . . . . .
N4 N 0.56784(15) 0.58379(12) 0.33585(17) 0.0322(5) Uani 1 1 d . . . . .
S1 S 0.27509(6) 0.92482(4) 0.49378(6) 0.0466(2) Uani 1 1 d . . . . .
C14 C 0.2859(2) 0.83327(19) 0.5023(2) 0.0389(7) Uani 1 1 d . . . . .
N5 N 0.2953(2) 0.76828(15) 0.5087(2) 0.0585(7) Uani 1 1 d . . . . .
C1 C 0.49479(19) 0.64106(14) 0.6881(2) 0.0336(6) Uani 1 1 d . . . . .
C2 C 0.6014(2) 0.63765(17) 0.7188(2) 0.0496(8) Uani 1 1 d . . . . .
H2 H 0.6298 0.6355 0.6637 0.059 Uiso 1 1 calc R U . . .
C3 C 0.6650(2) 0.63734(18) 0.8288(3) 0.0572(9) Uani 1 1 d . . . . .
H3 H 0.7362 0.6341 0.8473 0.069 Uiso 1 1 calc R U . . .
C4 C 0.6270(2) 0.64161(17) 0.9130(2) 0.0531(8) Uani 1 1 d . . . . .
H4 H 0.6716 0.6415 0.9876 0.064 Uiso 1 1 calc R U . . .
C5 C 0.5224(2) 0.64607(16) 0.8853(2) 0.0438(7) Uani 1 1 d . . . . .
H5 H 0.4959 0.6494 0.9418 0.053 Uiso 1 1 calc R U . . .
C6 C 0.45424(19) 0.64564(14) 0.7728(2) 0.0312(6) Uani 1 1 d . . . . .
C7 C 0.3459(2) 0.64105(15) 0.7512(2) 0.0370(6) Uani 1 1 d . . . . .
H7 H 0.3272 0.6417 0.8136 0.044 Uiso 1 1 calc R U . . .
C8 C 0.1676(2) 0.61929(15) 0.6587(2) 0.0394(7) Uani 1 1 d . . . . .
H8A H 0.1756 0.5947 0.7289 0.047 Uiso 1 1 calc R U . . .
H8B H 0.1311 0.5846 0.5984 0.047 Uiso 1 1 calc R U . . .
C9 C 0.1052(2) 0.69012(16) 0.6467(2) 0.0451(7) Uani 1 1 d . . . . .
H9A H 0.1450 0.7276 0.7007 0.054 Uiso 1 1 calc R U . . .
H9B H 0.0883 0.7111 0.5723 0.054 Uiso 1 1 calc R U . . .
C10 C 0.0292(2) 0.66453(19) 0.7851(2) 0.0506(8) Uani 1 1 d . . . . .
H10A H 0.0613 0.7106 0.8238 0.061 Uiso 1 1 calc R U . . .
H10B H 0.0768 0.6228 0.8157 0.061 Uiso 1 1 calc R U . . .
C11 C -0.0690(3) 0.6501(2) 0.8039(3) 0.0687(10) Uani 1 1 d . . . . .
H11A H -0.0998 0.6032 0.7673 0.082 Uiso 1 1 calc R U . . .
H11B H -0.0539 0.6446 0.8835 0.082 Uiso 1 1 calc DR U . . .
C12 C -0.1618(2) 0.7171(2) 0.6455(3) 0.0669(10) Uani 1 1 d . . . . .
H12A H -0.2113 0.7578 0.6155 0.080 Uiso 1 1 calc R U . . .
H12B H -0.1934 0.6704 0.6087 0.080 Uiso 1 1 calc DR U . . .
C13 C -0.0671(2) 0.73290(17) 0.6203(3) 0.0505(8) Uani 1 1 d . . . . .
H13A H -0.0854 0.7363 0.5399 0.061 Uiso 1 1 calc R U . . .
H14B H -0.0373 0.7811 0.6532 0.061 Uiso 1 1 calc R U . . .
C21 C 0.09236(19) 0.61273(14) 0.3326(2) 0.0319(6) Uani 1 1 d . . . . .
C22 C -0.0129(2) 0.59942(16) 0.3066(2) 0.0422(7) Uani 1 1 d . . . . .
H22 H -0.0422 0.6108 0.3591 0.051 Uiso 1 1 calc R U . . .
C23 C -0.0734(2) 0.57012(17) 0.2056(3) 0.0509(8) Uani 1 1 d . . . . .
H23 H -0.1429 0.5604 0.1911 0.061 Uiso 1 1 calc R U . . .
C24 C -0.0334(2) 0.55470(18) 0.1249(3) 0.0569(9) Uani 1 1 d . . . . .
H24 H -0.0754 0.5347 0.0562 0.068 Uiso 1 1 calc R U . . .
C25 C 0.0683(2) 0.56903(17) 0.1466(2) 0.0517(8) Uani 1 1 d . . . . .
H25 H 0.0950 0.5597 0.0914 0.062 Uiso 1 1 calc R U . . .
C26 C 0.13393(19) 0.59766(14) 0.2509(2) 0.0344(6) Uani 1 1 d . . . . .
C27 C 0.2395(2) 0.61373(15) 0.2664(2) 0.0352(6) Uani 1 1 d . . . . .
H27 H 0.2575 0.6079 0.2040 0.042 Uiso 1 1 calc R U . . .
C28 C 0.41265(19) 0.65188(14) 0.3485(2) 0.0352(6) Uani 1 1 d . . . . .
H28A H 0.4454 0.6936 0.3981 0.042 Uiso 1 1 calc R U . . .
H28B H 0.4020 0.6674 0.2726 0.042 Uiso 1 1 calc R U . . .
C29 C 0.4839(2) 0.58291(15) 0.3796(2) 0.0386(7) Uani 1 1 d . . . . .
H29A H 0.5143 0.5792 0.4605 0.046 Uiso 1 1 calc R U . . .
H29B H 0.4424 0.5377 0.3520 0.046 Uiso 1 1 calc R U . . .
C30 C 0.6238(2) 0.65557(16) 0.3524(2) 0.0428(7) Uani 1 1 d . . . . .
H30A H 0.6500 0.6687 0.4312 0.051 Uiso 1 1 calc R U . . .
H30B H 0.5770 0.6954 0.3115 0.051 Uiso 1 1 calc R U . . .
C31 C 0.7125(2) 0.64986(18) 0.3123(3) 0.0554(8) Uani 1 1 d . . . . .
H31A H 0.7475 0.6985 0.3220 0.067 Uiso 1 1 calc R U . . .
H31B H 0.7619 0.6127 0.3572 0.067 Uiso 1 1 calc R U . . .
C32 C 0.6241(3) 0.55863(18) 0.1825(3) 0.0570(9) Uani 1 1 d . . . . .
H32A H 0.6708 0.5195 0.2259 0.068 Uiso 1 1 calc R U . . .
H32B H 0.6006 0.5443 0.1042 0.068 Uiso 1 1 calc R U . . .
C33 C 0.5327(2) 0.56373(16) 0.2179(2) 0.0407(7) Uani 1 1 d . . . . .
H33A H 0.4847 0.6019 0.1735 0.049 Uiso 1 1 calc R U . . .
H33B H 0.4969 0.5154 0.2055 0.049 Uiso 1 1 calc R U . . .
O1W O 0.28620(15) 0.51084(11) 0.50379(17) 0.0436(5) Uani 1 1 d D . . . .
H11C H 0.2279(14) 0.4929(17) 0.488(2) 0.065 Uiso 1 1 d D U . . .
H11D H 0.3282(18) 0.4891(19) 0.547(3) 0.065 Uiso 1 1 d D U . . .
O2W O 0.08488(17) 0.45432(13) 0.4664(2) 0.0578(6) Uani 1 1 d D . . . .
H12C H 0.065(3) 0.4165(15) 0.423(3) 0.087 Uiso 1 1 d D U . . .
H12D H 0.051(5) 0.491(2) 0.428(6) 0.26(4) Uiso 1 1 d 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
Mn O1 1.8616(17) . ?
Mn O2 1.8708(17) . ?
Mn N1 2.043(2) . ?
Mn N2 2.047(2) . ?
Mn N5 2.218(3) . ?
Mn O1W 2.320(2) . ?
O1 C1 1.320(3) . ?
O2 C21 1.317(3) . ?
O3 C12 1.408(4) . ?
O3 C11 1.414(4) . ?
O4 C32 1.414(4) . ?
O4 C31 1.418(4) . ?
N1 C7 1.281(3) . ?
N1 C8 1.491(3) . ?
N2 C27 1.278(3) . ?
N2 C28 1.481(3) . ?
N3 C13 1.463(3) . ?
N3 C10 1.463(3) . ?
N3 C9 1.481(3) . ?
N4 C33 1.455(3) . ?
N4 C30 1.459(3) . ?
N4 C29 1.471(3) . ?
S1 C14 1.620(3) . ?
C14 N5 1.152(4) . ?
C1 C2 1.388(4) . ?
C1 C6 1.402(3) . ?
C2 C3 1.363(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.366(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.406(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.430(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.495(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.494(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.495(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H14B 0.9700 . ?
C21 C22 1.396(4) . ?
C21 C26 1.399(3) . ?
C22 C23 1.361(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.374(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.361(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.407(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.435(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.525(3) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.507(4) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.503(4) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
O1W H11C 0.824(17) . ?
O1W H11D 0.75(3) . ?
O2W H12C 0.846(18) . ?
O2W H12D 0.85(5) . ?

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 Mn O2 176.93(9) . . ?
O1 Mn N1 90.65(8) . . ?
O2 Mn N1 89.75(8) . . ?
O1 Mn N2 89.70(8) . . ?
O2 Mn N2 89.55(8) . . ?
N1 Mn N2 173.30(8) . . ?
O1 Mn N5 91.38(10) . . ?
O2 Mn N5 91.64(9) . . ?
N1 Mn N5 93.07(9) . . ?
N2 Mn N5 93.61(9) . . ?
O1 Mn O1W 89.56(8) . . ?
O2 Mn O1W 87.43(8) . . ?
N1 Mn O1W 86.82(8) . . ?
N2 Mn O1W 86.49(8) . . ?
N5 Mn O1W 179.06(9) . . ?
C1 O1 Mn 132.22(16) . . ?
C21 O2 Mn 130.30(15) . . ?
C12 O3 C11 108.7(2) . . ?
C32 O4 C31 109.8(2) . . ?
C7 N1 C8 115.9(2) . . ?
C7 N1 Mn 123.41(17) . . ?
C8 N1 Mn 120.51(16) . . ?
C27 N2 C28 116.1(2) . . ?
C27 N2 Mn 123.04(17) . . ?
C28 N2 Mn 120.84(16) . . ?
C13 N3 C10 108.5(2) . . ?
C13 N3 C9 110.1(2) . . ?
C10 N3 C9 110.9(2) . . ?
C33 N4 C30 108.5(2) . . ?
C33 N4 C29 112.8(2) . . ?
C30 N4 C29 114.2(2) . . ?
N5 C14 S1 178.9(3) . . ?
C14 N5 Mn 172.7(3) . . ?
O1 C1 C2 119.2(2) . . ?
O1 C1 C6 122.4(2) . . ?
C2 C1 C6 118.4(2) . . ?
C3 C2 C1 120.7(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 121.8(3) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 118.8(3) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.1(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 119.2(2) . . ?
C1 C6 C7 122.9(2) . . ?
C5 C6 C7 117.5(2) . . ?
N1 C7 C6 127.5(2) . . ?
N1 C7 H7 116.3 . . ?
C6 C7 H7 116.3 . . ?
N1 C8 C9 111.3(2) . . ?
N1 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
N3 C9 C8 109.4(2) . . ?
N3 C9 H9A 109.8 . . ?
C8 C9 H9A 109.8 . . ?
N3 C9 H9B 109.8 . . ?
C8 C9 H9B 109.8 . . ?
H9A C9 H9B 108.2 . . ?
N3 C10 C11 110.6(2) . . ?
N3 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
O3 C11 C10 110.8(3) . . ?
O3 C11 H11A 109.5 . . ?
C10 C11 H11A 109.5 . . ?
O3 C11 H11B 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
O3 C12 C13 112.3(3) . . ?
O3 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
O3 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
N3 C13 C12 110.0(2) . . ?
N3 C13 H13A 109.7 . . ?
C12 C13 H13A 109.7 . . ?
N3 C13 H14B 109.7 . . ?
C12 C13 H14B 109.7 . . ?
H13A C13 H14B 108.2 . . ?
O2 C21 C22 119.6(2) . . ?
O2 C21 C26 121.9(2) . . ?
C22 C21 C26 118.4(2) . . ?
C23 C22 C21 121.1(3) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C22 C23 C24 121.0(3) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C25 C24 C23 119.3(3) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C24 C25 C26 121.4(3) . . ?
C24 C25 H25 119.3 . . ?
C26 C25 H25 119.3 . . ?
C21 C26 C25 118.7(2) . . ?
C21 C26 C27 122.9(2) . . ?
C25 C26 C27 118.2(2) . . ?
N2 C27 C26 126.9(2) . . ?
N2 C27 H27 116.5 . . ?
C26 C27 H27 116.5 . . ?
N2 C28 C29 111.5(2) . . ?
N2 C28 H28A 109.3 . . ?
C29 C28 H28A 109.3 . . ?
N2 C28 H28B 109.3 . . ?
C29 C28 H28B 109.3 . . ?
H28A C28 H28B 108.0 . . ?
N4 C29 C28 115.0(2) . . ?
N4 C29 H29A 108.5 . . ?
C28 C29 H29A 108.5 . . ?
N4 C29 H29B 108.5 . . ?
C28 C29 H29B 108.5 . . ?
H29A C29 H29B 107.5 . . ?
N4 C30 C31 110.7(2) . . ?
N4 C30 H30A 109.5 . . ?
C31 C30 H30A 109.5 . . ?
N4 C30 H30B 109.5 . . ?
C31 C30 H30B 109.5 . . ?
H30A C30 H30B 108.1 . . ?
O4 C31 C30 111.2(2) . . ?
O4 C31 H31A 109.4 . . ?
C30 C31 H31A 109.4 . . ?
O4 C31 H31B 109.4 . . ?
C30 C31 H31B 109.4 . . ?
H31A C31 H31B 108.0 . . ?
O4 C32 C33 111.5(2) . . ?
O4 C32 H32A 109.3 . . ?
C33 C32 H32A 109.3 . . ?
O4 C32 H32B 109.3 . . ?
C33 C32 H32B 109.3 . . ?
H32A C32 H32B 108.0 . . ?
N4 C33 C32 109.5(2) . . ?
N4 C33 H33A 109.8 . . ?
C32 C33 H33A 109.8 . . ?
N4 C33 H33B 109.8 . . ?
C32 C33 H33B 109.8 . . ?
H33A C33 H33B 108.2 . . ?
Mn O1W H11C 115(2) . . ?
Mn O1W H11D 119(3) . . ?
H11C O1W H11D 114(3) . . ?
H12C O2W H12D 104(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Mn O1 C1 -8.5(2) . . . . ?
N2 Mn O1 C1 178.2(2) . . . . ?
N5 Mn O1 C1 84.6(2) . . . . ?
O1W Mn O1 C1 -95.3(2) . . . . ?
N1 Mn O2 C21 -147.4(2) . . . . ?
N2 Mn O2 C21 26.0(2) . . . . ?
N5 Mn O2 C21 119.6(2) . . . . ?
O1W Mn O2 C21 -60.6(2) . . . . ?
Mn O1 C1 C2 -178.8(2) . . . . ?
Mn O1 C1 C6 2.9(4) . . . . ?
O1 C1 C2 C3 -177.1(3) . . . . ?
C6 C1 C2 C3 1.2(4) . . . . ?
C1 C2 C3 C4 -1.1(5) . . . . ?
C2 C3 C4 C5 0.2(5) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
O1 C1 C6 C5 177.8(2) . . . . ?
C2 C1 C6 C5 -0.5(4) . . . . ?
O1 C1 C6 C7 5.3(4) . . . . ?
C2 C1 C6 C7 -172.9(3) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
C4 C5 C6 C7 172.5(3) . . . . ?
C8 N1 C7 C6 170.2(2) . . . . ?
Mn N1 C7 C6 -5.2(4) . . . . ?
C1 C6 C7 N1 -3.6(4) . . . . ?
C5 C6 C7 N1 -176.2(3) . . . . ?
C7 N1 C8 C9 97.9(3) . . . . ?
Mn N1 C8 C9 -86.5(2) . . . . ?
C13 N3 C9 C8 -162.0(2) . . . . ?
C10 N3 C9 C8 77.9(3) . . . . ?
N1 C8 C9 N3 -172.2(2) . . . . ?
C13 N3 C10 C11 56.3(3) . . . . ?
C9 N3 C10 C11 177.4(2) . . . . ?
C12 O3 C11 C10 59.9(4) . . . . ?
N3 C10 C11 O3 -59.8(4) . . . . ?
C11 O3 C12 C13 -59.9(4) . . . . ?
C10 N3 C13 C12 -55.1(3) . . . . ?
C9 N3 C13 C12 -176.6(3) . . . . ?
O3 C12 C13 N3 58.5(4) . . . . ?
Mn O2 C21 C22 161.86(19) . . . . ?
Mn O2 C21 C26 -20.5(4) . . . . ?
O2 C21 C22 C23 179.8(3) . . . . ?
C26 C21 C22 C23 2.2(4) . . . . ?
C21 C22 C23 C24 -1.9(4) . . . . ?
C22 C23 C24 C25 0.0(5) . . . . ?
C23 C24 C25 C26 1.5(5) . . . . ?
O2 C21 C26 C25 -178.3(2) . . . . ?
C22 C21 C26 C25 -0.7(4) . . . . ?
O2 C21 C26 C27 -1.6(4) . . . . ?
C22 C21 C26 C27 176.0(2) . . . . ?
C24 C25 C26 C21 -1.1(4) . . . . ?
C24 C25 C26 C27 -178.0(3) . . . . ?
C28 N2 C27 C26 -176.9(2) . . . . ?
Mn N2 C27 C26 5.8(4) . . . . ?
C21 C26 C27 N2 8.0(4) . . . . ?
C25 C26 C27 N2 -175.3(3) . . . . ?
C27 N2 C28 C29 -93.7(3) . . . . ?
Mn N2 C28 C29 83.7(2) . . . . ?
C33 N4 C29 C28 -77.7(3) . . . . ?
C30 N4 C29 C28 46.9(3) . . . . ?
N2 C28 C29 N4 158.5(2) . . . . ?
C33 N4 C30 C31 -57.0(3) . . . . ?
C29 N4 C30 C31 176.2(2) . . . . ?
C32 O4 C31 C30 -57.4(3) . . . . ?
N4 C30 C31 O4 57.4(3) . . . . ?
C31 O4 C32 C33 59.1(3) . . . . ?
C30 N4 C33 C32 57.8(3) . . . . ?
C29 N4 C33 C32 -174.6(2) . . . . ?
O4 C32 C33 N4 -60.1(3) . . . . ?

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.043

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1841249'
_audit_update_record             
;
2018-07-24 deposited with the CCDC.
2018-07-27 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         
'C28 H38 Cl1.12 Mn N6.88 O2 S0.88, 1.12(C H4 O), C28 H38 Mn N8 O2 S2, 2(C N S)'
_chemical_formula_sum            'C58 H80.48 Cl1.12 Mn2 N16.88 O5.12 S4.88'
_chemical_formula_weight         1402.14

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'
S S 0.1246 0.1234 '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      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                   10.5565(4)
_cell_length_b                   11.1309(4)
_cell_length_c                   16.0329(6)
_cell_angle_alpha                69.9980(10)
_cell_angle_beta                 79.391(2)
_cell_angle_gamma                81.774(2)
_cell_volume                     1733.47(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2033
_cell_measurement_theta_min      3.38
_cell_measurement_theta_max      26.78

_exptl_crystal_description       cube
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             735
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_absorpt_coefficient_mu    0.612
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.756
_exptl_absorpt_correction_T_max  0.825
_exptl_absorpt_process_detail    'Bruker SADABS'

_exptl_absorpt_special_details   
'Bruker (2009). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.'

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27093
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.129
_diffrn_reflns_theta_max         27.875
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             8237
_reflns_number_gt                6225
_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    'SHELX97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep3 for Windows (Farrugia,1997)'
_computing_publication_material  'Wingx 2013.3 (Farrugia, 1999)'

_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)+(0.0410P)²+1.0450P] 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         8237
_refine_ls_number_parameters     449
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1196
_refine_ls_wR_factor_gt          0.1069
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.005
_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 0.5000 0.5000 0.5000 0.03998(12) Uani 1 2 d S . P . .
N4 N 0.3156(15) 0.3974(19) 0.5976(13) 0.084(6) Uani 0.440(5) 1 d . . P A 1
C14 C 0.2592(6) 0.3114(7) 0.6257(3) 0.0483(15) Uani 0.440(5) 1 d . . P A 1
S1 S 0.1732(2) 0.1859(3) 0.66654(14) 0.0801(10) Uani 0.440(5) 1 d . . P A 1
Cl1 Cl 0.2908(4) 0.4074(3) 0.6067(3) 0.0546(6) Uani 0.560(5) 1 d . . P A 2
O3 O 0.2294(5) 0.1278(4) 0.7079(3) 0.0842(13) Uani 0.560(5) 1 d . . P A 2
H3M H 0.2640 0.1905 0.6720 0.126 Uiso 0.560(5) 1 calc R U P A 2
C3M C 0.1174(10) 0.1170(9) 0.6808(6) 0.134(4) Uani 0.560(5) 1 d . . P A 2
H3M1 H 0.0696 0.0531 0.7275 0.202 Uiso 0.560(5) 1 calc R U P A 2
H3M2 H 0.1376 0.0924 0.6276 0.202 Uiso 0.560(5) 1 calc R U P A 2
H3M3 H 0.0663 0.1980 0.6681 0.202 Uiso 0.560(5) 1 calc R U P A 2
O1 O 0.56251(16) 0.34252(15) 0.48569(11) 0.0527(4) Uani 1 1 d . . . . .
N1 N 0.58684(15) 0.45296(16) 0.61261(11) 0.0368(4) Uani 1 1 d . . . . .
N2 N 0.79107(15) 0.58968(16) 0.63819(11) 0.0381(4) Uani 1 1 d . . . . .
N3 N 1.05382(19) 0.5691(2) 0.66464(16) 0.0653(6) Uani 1 1 d . . . . .
H3A H 1.0623 0.6385 0.6782 0.078 Uiso 1 1 calc R U . . .
H3B H 1.1301 0.5232 0.6649 0.078 Uiso 1 1 calc R U . . .
C1 C 0.6577(2) 0.25928(19) 0.51833(14) 0.0425(5) Uani 1 1 d . . . . .
C2 C 0.7082(3) 0.1661(2) 0.47810(18) 0.0606(6) Uani 1 1 d . . . . .
H2 H 0.6764 0.1658 0.4278 0.073 Uiso 1 1 calc R U . . .
C3 C 0.8046(3) 0.0744(3) 0.5120(2) 0.0721(8) Uani 1 1 d . . . . .
H3 H 0.8368 0.0129 0.4844 0.087 Uiso 1 1 calc R U . . .
C4 C 0.8542(3) 0.0724(3) 0.5862(2) 0.0721(8) Uani 1 1 d . . . . .
H4 H 0.9189 0.0100 0.6087 0.086 Uiso 1 1 calc R U . . .
C5 C 0.8071(2) 0.1632(2) 0.62631(18) 0.0572(6) Uani 1 1 d . . . . .
H5 H 0.8401 0.1617 0.6766 0.069 Uiso 1 1 calc R U . . .
C6 C 0.70944(19) 0.25924(19) 0.59286(14) 0.0409(4) Uani 1 1 d . . . . .
C7 C 0.66582(19) 0.35265(19) 0.63793(13) 0.0401(4) Uani 1 1 d . . . . .
H7 H 0.6981 0.3391 0.6909 0.048 Uiso 1 1 calc R U . . .
C8 C 0.56405(19) 0.5377(2) 0.66802(14) 0.0427(5) Uani 1 1 d . . . . .
H8A H 0.5760 0.4879 0.7293 0.051 Uiso 1 1 calc R U . . .
H8B H 0.4757 0.5766 0.6685 0.051 Uiso 1 1 calc R U . . .
C9 C 0.65690(19) 0.6418(2) 0.63100(14) 0.0425(5) Uani 1 1 d . . . . .
H9A H 0.6487 0.6874 0.5685 0.051 Uiso 1 1 calc R U . . .
H9B H 0.6339 0.7028 0.6635 0.051 Uiso 1 1 calc R U . . .
C10 C 0.8240(2) 0.5625(3) 0.72720(15) 0.0526(6) Uani 1 1 d . . . . .
H10A H 0.7608 0.5105 0.7716 0.063 Uiso 1 1 calc R U . . .
H10B H 0.8222 0.6422 0.7396 0.063 Uiso 1 1 calc R U . . .
C11 C 0.9572(3) 0.4921(3) 0.7332(2) 0.0701(7) Uani 1 1 d . . . . .
H11A H 0.9795 0.4757 0.7924 0.084 Uiso 1 1 calc R U . . .
H11B H 0.9574 0.4102 0.7243 0.084 Uiso 1 1 calc R U . . .
C12 C 1.0163(3) 0.6090(4) 0.57444(19) 0.0788(9) Uani 1 1 d . . . . .
H12A H 1.0213 0.5344 0.5554 0.095 Uiso 1 1 calc R U . . .
H12B H 1.0762 0.6677 0.5323 0.095 Uiso 1 1 calc R U . . .
C13 C 0.8815(2) 0.6734(3) 0.57378(16) 0.0616(7) Uani 1 1 d . . . . .
H13A H 0.8780 0.7518 0.5881 0.074 Uiso 1 1 calc R U . . .
H13B H 0.8577 0.6959 0.5143 0.074 Uiso 1 1 calc R U . . .
Mn2 Mn 0.5000 0.5000 1.0000 0.04572(13) Uani 1 2 d S . P . .
O2 O 0.53910(18) 0.40073(16) 1.11384(11) 0.0625(5) Uani 1 1 d . . . . .
N5 N 0.33750(17) 0.40353(17) 1.02385(12) 0.0448(4) Uani 1 1 d . . . . .
N6 N 0.27978(18) 0.26317(18) 0.90686(12) 0.0492(4) Uani 1 1 d . . . . .
N7 N 0.2470(2) 0.0255(2) 0.88713(16) 0.0651(6) Uani 1 1 d . . . . .
H7A H 0.2459 0.0476 0.8284 0.078 Uiso 1 1 calc R U . . .
H7B H 0.2382 -0.0582 0.9113 0.078 Uiso 1 1 calc R U . . .
S2 S 0.78429(9) 0.18107(8) 0.87444(6) 0.0830(3) Uani 1 1 d . . . . .
C15 C 0.6890(2) 0.2816(2) 0.91635(15) 0.0499(5) Uani 1 1 d . . . . .
N8 N 0.6196(2) 0.3524(2) 0.94396(18) 0.0736(7) Uani 1 1 d . . . . .
C21 C 0.5095(2) 0.2840(2) 1.16307(14) 0.0467(5) Uani 1 1 d . . . . .
C22 C 0.5864(2) 0.2120(2) 1.22829(16) 0.0552(6) Uani 1 1 d . . . . .
H22 H 0.6607 0.2442 1.2324 0.066 Uiso 1 1 calc R U . . .
C23 C 0.5536(3) 0.0946(3) 1.28626(18) 0.0645(7) Uani 1 1 d . . . . .
H23 H 0.6056 0.0479 1.3295 0.077 Uiso 1 1 calc R U . . .
C24 C 0.4433(3) 0.0447(3) 1.2809(2) 0.0723(8) Uani 1 1 d . . . . .
H24 H 0.4208 -0.0347 1.3209 0.087 Uiso 1 1 calc R U . . .
C25 C 0.3676(3) 0.1130(2) 1.21637(18) 0.0614(6) Uani 1 1 d . . . . .
H25 H 0.2934 0.0796 1.2132 0.074 Uiso 1 1 calc R U . . .
C26 C 0.4000(2) 0.2323(2) 1.15516(14) 0.0454(5) Uani 1 1 d . . . . .
C27 C 0.3168(2) 0.2987(2) 1.08879(15) 0.0469(5) Uani 1 1 d . . . . .
H27 H 0.2407 0.2623 1.0933 0.056 Uiso 1 1 calc R U . . .
C28 C 0.2441(2) 0.4505(2) 0.95994(18) 0.0571(6) Uani 1 1 d . . . . .
H28A H 0.2354 0.5436 0.9387 0.068 Uiso 1 1 calc R U . . .
H28B H 0.1601 0.4209 0.9892 0.068 Uiso 1 1 calc R U . . .
C29 C 0.2913(3) 0.4007(3) 0.88116(17) 0.0646(7) Uani 1 1 d . . . . .
H29A H 0.2410 0.4462 0.8330 0.078 Uiso 1 1 calc R U . . .
H29B H 0.3810 0.4177 0.8590 0.078 Uiso 1 1 calc R U . . .
C30 C 0.3851(2) 0.1945(3) 0.86445(18) 0.0631(7) Uani 1 1 d . . . . .
H30A H 0.4673 0.2129 0.8742 0.076 Uiso 1 1 calc R U . . .
H30B H 0.3833 0.2230 0.8003 0.076 Uiso 1 1 calc R U . . .
C31 C 0.3725(3) 0.0528(3) 0.9028(2) 0.0692(7) Uani 1 1 d . . . . .
H31A H 0.4430 0.0074 0.8745 0.083 Uiso 1 1 calc R U . . .
H31B H 0.3768 0.0234 0.9667 0.083 Uiso 1 1 calc R U . . .
C32 C 0.1378(2) 0.0976(2) 0.92701(18) 0.0566(6) Uani 1 1 d . . . . .
H32A H 0.1334 0.0674 0.9918 0.068 Uiso 1 1 calc R U . . .
H32B H 0.0571 0.0829 0.9128 0.068 Uiso 1 1 calc R U . . .
C33 C 0.1560(2) 0.2385(2) 0.89090(17) 0.0506(5) Uani 1 1 d . . . . .
H33A H 0.1521 0.2699 0.8270 0.061 Uiso 1 1 calc R U . . .
H34B H 0.0865 0.2844 0.9196 0.061 Uiso 1 1 calc R U . . .
S3 S 1.0482(2) 0.8049(3) 0.89610(14) 0.0970(9) Uani 0.720(6) 1 d . U P . .
C16 C 1.0552(3) 0.7835(4) 0.7981(3) 0.0813(10) Uani 1 1 d . . . . .
N9 N 1.0711(11) 0.7641(11) 0.7315(5) 0.107(3) Uani 0.720(6) 1 d . . P . .
S3A S 1.0014(5) 0.8950(10) 0.8437(7) 0.131(3) Uani 0.280(6) 1 d . U P . .
N9A N 1.069(4) 0.714(3) 0.7693(16) 0.132(9) Uani 0.280(6) 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 O1 1.8571(14) 2_666 ?
Mn1 O1 1.8572(14) . ?
Mn1 N1 2.0494(16) . ?
Mn1 N1 2.0494(16) 2_666 ?
Mn1 N4 2.415(16) 2_666 ?
Mn1 N4 2.415(16) . ?
Mn1 Cl1 2.630(4) . ?
Mn1 Cl1 2.630(4) 2_666 ?
N4 C14 1.115(17) . ?
C14 S1 1.651(9) . ?
O3 C3M 1.367(9) . ?
O3 H3M 0.8200 . ?
C3M H3M1 0.9600 . ?
C3M H3M2 0.9600 . ?
C3M H3M3 0.9600 . ?
O1 C1 1.318(2) . ?
N1 C7 1.286(3) . ?
N1 C8 1.472(3) . ?
N2 C13 1.442(3) . ?
N2 C10 1.451(3) . ?
N2 C9 1.461(2) . ?
N3 C12 1.472(3) . ?
N3 C11 1.475(4) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
C1 C2 1.396(3) . ?
C1 C6 1.402(3) . ?
C2 C3 1.379(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.366(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.410(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.439(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.515(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.511(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.499(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
Mn2 O2 1.8682(17) . ?
Mn2 O2 1.8682(17) 2_667 ?
Mn2 N5 2.0607(17) 2_667 ?
Mn2 N5 2.0607(17) . ?
Mn2 N8 2.258(2) . ?
Mn2 N8 2.258(2) 2_667 ?
O2 C21 1.316(3) . ?
N5 C27 1.285(3) . ?
N5 C28 1.467(3) . ?
N6 C30 1.455(3) . ?
N6 C33 1.457(3) . ?
N6 C29 1.460(3) . ?
N7 C32 1.482(3) . ?
N7 C31 1.483(3) . ?
N7 H7A 0.8900 . ?
N7 H7B 0.8900 . ?
S2 C15 1.631(3) . ?
C15 N8 1.143(3) . ?
C21 C22 1.395(3) . ?
C21 C26 1.407(3) . ?
C22 C23 1.368(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.388(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.371(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.399(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.439(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.523(4) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.500(4) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.502(3) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H34B 0.9700 . ?
S3 S3A 1.179(10) . ?
S3 C16 1.655(4) . ?
C16 N9A 1.01(3) . ?
C16 N9 1.139(10) . ?
C16 S3A 1.632(6) . ?
N9 N9A 0.67(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Mn1 O1 180.0 2_666 . ?
O1 Mn1 N1 89.53(6) 2_666 . ?
O1 Mn1 N1 90.47(6) . . ?
O1 Mn1 N1 90.47(6) 2_666 2_666 ?
O1 Mn1 N1 89.52(6) . 2_666 ?
N1 Mn1 N1 180.0 . 2_666 ?
O1 Mn1 N4 87.9(5) 2_666 2_666 ?
O1 Mn1 N4 92.1(5) . 2_666 ?
N1 Mn1 N4 93.1(5) . 2_666 ?
N1 Mn1 N4 86.9(5) 2_666 2_666 ?
O1 Mn1 N4 92.1(5) 2_666 . ?
O1 Mn1 N4 87.9(5) . . ?
N1 Mn1 N4 86.9(5) . . ?
N1 Mn1 N4 93.1(5) 2_666 . ?
N4 Mn1 N4 180.0 2_666 . ?
O1 Mn1 Cl1 87.29(9) 2_666 . ?
O1 Mn1 Cl1 92.71(9) . . ?
N1 Mn1 Cl1 87.39(11) . . ?
N1 Mn1 Cl1 92.61(11) 2_666 . ?
O1 Mn1 Cl1 92.71(9) 2_666 2_666 ?
O1 Mn1 Cl1 87.29(9) . 2_666 ?
N1 Mn1 Cl1 92.61(11) . 2_666 ?
N1 Mn1 Cl1 87.39(11) 2_666 2_666 ?
Cl1 Mn1 Cl1 180.0 . 2_666 ?
C14 N4 Mn1 148.7(13) . . ?
N4 C14 S1 178.9(11) . . ?
C3M O3 H3M 109.5 . . ?
O3 C3M H3M1 109.5 . . ?
O3 C3M H3M2 109.5 . . ?
H3M1 C3M H3M2 109.5 . . ?
O3 C3M H3M3 109.5 . . ?
H3M1 C3M H3M3 109.5 . . ?
H3M2 C3M H3M3 109.5 . . ?
C1 O1 Mn1 131.05(14) . . ?
C7 N1 C8 116.08(17) . . ?
C7 N1 Mn1 123.54(14) . . ?
C8 N1 Mn1 120.35(13) . . ?
C13 N2 C10 108.75(18) . . ?
C13 N2 C9 112.15(17) . . ?
C10 N2 C9 112.93(16) . . ?
C12 N3 C11 111.6(2) . . ?
C12 N3 H3A 109.3 . . ?
C11 N3 H3A 109.3 . . ?
C12 N3 H3B 109.3 . . ?
C11 N3 H3B 109.3 . . ?
H3A N3 H3B 108.0 . . ?
O1 C1 C2 118.9(2) . . ?
O1 C1 C6 122.64(19) . . ?
C2 C1 C6 118.4(2) . . ?
C3 C2 C1 120.8(3) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C4 C3 C2 121.0(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 119.3(2) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 121.2(2) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 119.2(2) . . ?
C1 C6 C7 122.68(18) . . ?
C5 C6 C7 118.1(2) . . ?
N1 C7 C6 126.82(19) . . ?
N1 C7 H7 116.6 . . ?
C6 C7 H7 116.6 . . ?
N1 C8 C9 110.18(16) . . ?
N1 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
N1 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
N2 C9 C8 112.02(17) . . ?
N2 C9 H9A 109.2 . . ?
C8 C9 H9A 109.2 . . ?
N2 C9 H9B 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
N2 C10 C11 109.9(2) . . ?
N2 C10 H10A 109.7 . . ?
C11 C10 H10A 109.7 . . ?
N2 C10 H10B 109.7 . . ?
C11 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
N3 C11 C10 110.2(2) . . ?
N3 C11 H11A 109.6 . . ?
C10 C11 H11A 109.6 . . ?
N3 C11 H11B 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
N3 C12 C13 111.0(2) . . ?
N3 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
N3 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
N2 C13 C12 110.6(2) . . ?
N2 C13 H13A 109.5 . . ?
C12 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
O2 Mn2 O2 180.00(11) . 2_667 ?
O2 Mn2 N5 90.32(7) . 2_667 ?
O2 Mn2 N5 89.67(7) 2_667 2_667 ?
O2 Mn2 N5 89.68(7) . . ?
O2 Mn2 N5 90.32(7) 2_667 . ?
N5 Mn2 N5 180.0 2_667 . ?
O2 Mn2 N8 89.05(9) . . ?
O2 Mn2 N8 90.95(9) 2_667 . ?
N5 Mn2 N8 89.41(8) 2_667 . ?
N5 Mn2 N8 90.59(8) . . ?
O2 Mn2 N8 90.95(9) . 2_667 ?
O2 Mn2 N8 89.06(9) 2_667 2_667 ?
N5 Mn2 N8 90.59(8) 2_667 2_667 ?
N5 Mn2 N8 89.41(8) . 2_667 ?
N8 Mn2 N8 180.0 . 2_667 ?
C21 O2 Mn2 129.54(15) . . ?
C27 N5 C28 117.34(19) . . ?
C27 N5 Mn2 123.64(16) . . ?
C28 N5 Mn2 118.86(14) . . ?
C30 N6 C33 110.06(18) . . ?
C30 N6 C29 114.3(2) . . ?
C33 N6 C29 111.15(19) . . ?
C32 N7 C31 110.9(2) . . ?
C32 N7 H7A 109.5 . . ?
C31 N7 H7A 109.5 . . ?
C32 N7 H7B 109.5 . . ?
C31 N7 H7B 109.5 . . ?
H7A N7 H7B 108.0 . . ?
N8 C15 S2 177.9(2) . . ?
C15 N8 Mn2 174.3(2) . . ?
O2 C21 C22 118.5(2) . . ?
O2 C21 C26 122.3(2) . . ?
C22 C21 C26 119.1(2) . . ?
C23 C22 C21 120.8(2) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 120.4(3) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C25 C24 C23 119.7(3) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 121.1(2) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 H25 119.4 . . ?
C25 C26 C21 118.8(2) . . ?
C25 C26 C27 118.3(2) . . ?
C21 C26 C27 122.9(2) . . ?
N5 C27 C26 126.2(2) . . ?
N5 C27 H27 116.9 . . ?
C26 C27 H27 116.9 . . ?
N5 C28 C29 109.1(2) . . ?
N5 C28 H28A 109.9 . . ?
C29 C28 H28A 109.9 . . ?
N5 C28 H28B 109.9 . . ?
C29 C28 H28B 109.9 . . ?
H28A C28 H28B 108.3 . . ?
N6 C29 C28 111.6(2) . . ?
N6 C29 H29A 109.3 . . ?
C28 C29 H29A 109.3 . . ?
N6 C29 H29B 109.3 . . ?
C28 C29 H29B 109.3 . . ?
H29A C29 H29B 108.0 . . ?
N6 C30 C31 110.2(2) . . ?
N6 C30 H30A 109.6 . . ?
C31 C30 H30A 109.6 . . ?
N6 C30 H30B 109.6 . . ?
C31 C30 H30B 109.6 . . ?
H30A C30 H30B 108.1 . . ?
N7 C31 C30 109.2(2) . . ?
N7 C31 H31A 109.8 . . ?
C30 C31 H31A 109.8 . . ?
N7 C31 H31B 109.8 . . ?
C30 C31 H31B 109.8 . . ?
H31A C31 H31B 108.3 . . ?
N7 C32 C33 109.9(2) . . ?
N7 C32 H32A 109.7 . . ?
C33 C32 H32A 109.7 . . ?
N7 C32 H32B 109.7 . . ?
C33 C32 H32B 109.7 . . ?
H32A C32 H32B 108.2 . . ?
N6 C33 C32 111.10(19) . . ?
N6 C33 H33A 109.4 . . ?
C32 C33 H33A 109.4 . . ?
N6 C33 H34B 109.4 . . ?
C32 C33 H34B 109.4 . . ?
H33A C33 H34B 108.0 . . ?
S3A S3 C16 67.9(3) . . ?
N9A C16 N9 35.5(15) . . ?
N9A C16 S3A 168(2) . . ?
N9 C16 S3A 142.3(7) . . ?
N9A C16 S3 141.9(15) . . ?
N9 C16 S3 173.9(7) . . ?
S3A C16 S3 42.0(4) . . ?
N9A N9 C16 61(3) . . ?
S3 S3A C16 70.0(4) . . ?
N9 N9A C16 83(4) . . ?

_refine_diff_density_max         0.263
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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 1841247'
_audit_update_record             
;
2018-07-24 deposited with the CCDC.
2018-07-27 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         'C26 H38 Mn N4 O6, Br'
_chemical_formula_sum            'C26 H38 Br Mn N4 O6'
_chemical_formula_weight         637.45

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

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

_cell_length_a                   18.0383(6)
_cell_length_b                   6.8439(2)
_cell_length_c                   23.7518(8)
_cell_angle_alpha                90
_cell_angle_beta                 100.353(2)
_cell_angle_gamma                90
_cell_volume                     2884.48(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2313
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      24.10

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_F_000             1320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.33
_exptl_absorpt_coefficient_mu    1.888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.433
_exptl_absorpt_correction_T_max  0.603
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_absorpt_special_details   
'Bruker (2009). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.'

_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  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30615
_diffrn_reflns_av_unetI/netI     0.0103
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.295
_diffrn_reflns_theta_max         25.055
_diffrn_reflns_theta_full        25.055
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000

_reflns_number_total             2556
_reflns_number_gt                2315
_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    'SHELX97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep3 for Windows (Farrugia,1997)'
_computing_publication_material  'Wingx 2013.3 (Farrugia, 1999)'

_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)+(0.0327P)²+2.9605P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2556
_refine_ls_number_parameters     180
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0241
_refine_ls_wR_factor_ref         0.0651
_refine_ls_wR_factor_gt          0.0625
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
Mn Mn 0.5000 0.0000 0.5000 0.02759(11) Uani 1 2 d S . P . .
O1W O 0.42255(8) -0.16991(18) 0.54295(6) 0.0351(3) Uani 1 1 d . . . . .
H11 H 0.3800(14) -0.197(3) 0.5231(10) 0.053 Uiso 1 1 d . U . . .
H12 H 0.4122(13) -0.106(4) 0.5668(10) 0.053 Uiso 1 1 d . U . . .
Br1 Br 0.2500 0.67066(5) 0.5000 0.05406(12) Uani 1 2 d S T P . .
N1 N 0.44252(8) 0.2493(2) 0.51310(6) 0.0316(3) Uani 1 1 d . . . . .
N2 N 0.38148(8) 0.0746(2) 0.62154(6) 0.0353(3) Uani 1 1 d . . . . .
O1 O 0.43634(7) -0.03833(18) 0.42924(5) 0.0385(3) Uani 1 1 d . . . . .
O2 O 0.36474(12) -0.1986(3) 0.70968(8) 0.0750(5) Uani 1 1 d . . . . .
C1 C 0.40315(9) 0.0976(3) 0.39386(8) 0.0358(4) Uani 1 1 d . . . . .
C2 C 0.37798(10) 0.0490(4) 0.33606(8) 0.0465(5) Uani 1 1 d . . . . .
H2 H 0.3832 -0.0783 0.3237 0.056 Uiso 1 1 calc R U . . .
C3 C 0.34572(12) 0.1884(4) 0.29790(9) 0.0609(7) Uani 1 1 d . . . . .
H3 H 0.3303 0.1545 0.2597 0.073 Uiso 1 1 calc R U . . .
C4 C 0.33564(14) 0.3781(5) 0.31493(11) 0.0682(7) Uani 1 1 d . . . . .
H4 H 0.3152 0.4720 0.2883 0.082 Uiso 1 1 calc R U . . .
C5 C 0.35604(13) 0.4255(4) 0.37129(10) 0.0584(6) Uani 1 1 d . . . . .
H5 H 0.3472 0.5514 0.3832 0.070 Uiso 1 1 calc R U . . .
C6 C 0.39036(10) 0.2877(3) 0.41190(8) 0.0402(4) Uani 1 1 d . . . . .
C7 C 0.40561(10) 0.3459(3) 0.47090(8) 0.0393(4) Uani 1 1 d . . . . .
H7 H 0.3867 0.4666 0.4795 0.047 Uiso 1 1 calc R U . . .
C8 C 0.44363(12) 0.3337(3) 0.57091(8) 0.0404(4) Uani 1 1 d . . . . .
H8A H 0.4444 0.4750 0.5682 0.049 Uiso 1 1 calc R U . . .
H8B H 0.4895 0.2931 0.5960 0.049 Uiso 1 1 calc R U . . .
C9 C 0.37626(12) 0.2718(3) 0.59707(9) 0.0457(5) Uani 1 1 d . . . . .
H9A H 0.3703 0.3642 0.6269 0.055 Uiso 1 1 calc R U . . .
H9B H 0.3313 0.2793 0.5678 0.055 Uiso 1 1 calc R U . . .
C10 C 0.30716(12) 0.0091(3) 0.63163(10) 0.0506(5) Uani 1 1 d . . . . .
H10A H 0.2718 0.0072 0.5957 0.061 Uiso 1 1 calc R U . . .
H10B H 0.2885 0.1002 0.6571 0.061 Uiso 1 1 calc R U . . .
C11 C 0.31242(15) -0.1902(4) 0.65757(11) 0.0639(7) Uani 1 1 d . . . . .
H11A H 0.2631 -0.2289 0.6645 0.077 Uiso 1 1 calc R U . . .
H11B H 0.3274 -0.2824 0.6307 0.077 Uiso 1 1 calc R U . . .
C12 C 0.43650(16) -0.1366(4) 0.70044(12) 0.0740(8) Uani 1 1 d . . . . .
H12A H 0.4545 -0.2264 0.6743 0.089 Uiso 1 1 calc R U . . .
H12B H 0.4718 -0.1396 0.7364 0.089 Uiso 1 1 calc R U . . .
C13 C 0.43389(12) 0.0675(4) 0.67590(9) 0.0502(5) Uani 1 1 d . . . . .
H13A H 0.4180 0.1589 0.7026 0.060 Uiso 1 1 calc R U . . .
H13B H 0.4838 0.1054 0.6701 0.060 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
Mn O1 1.8757(12) 5_656 ?
Mn O1 1.8757(12) . ?
Mn N1 2.0490(14) . ?
Mn N1 2.0490(14) 5_656 ?
Mn O1W 2.2037(13) 5_656 ?
Mn O1W 2.2038(13) . ?
O1W H11 0.85(3) . ?
O1W H12 0.76(2) . ?
N1 C7 1.283(2) . ?
N1 C8 1.486(2) . ?
N2 C13 1.458(2) . ?
N2 C9 1.466(3) . ?
N2 C10 1.473(2) . ?
O1 C1 1.323(2) . ?
O2 C11 1.416(3) . ?
O2 C12 1.416(3) . ?
C1 C6 1.402(3) . ?
C1 C2 1.406(3) . ?
C2 C3 1.371(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.362(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.410(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.435(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.521(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.493(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.511(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Mn O1 180.0 5_656 . ?
O1 Mn N1 89.57(6) 5_656 . ?
O1 Mn N1 90.43(6) . . ?
O1 Mn N1 90.43(6) 5_656 5_656 ?
O1 Mn N1 89.57(6) . 5_656 ?
N1 Mn N1 180.00(4) . 5_656 ?
O1 Mn O1W 90.23(6) 5_656 5_656 ?
O1 Mn O1W 89.77(6) . 5_656 ?
N1 Mn O1W 90.64(5) . 5_656 ?
N1 Mn O1W 89.36(5) 5_656 5_656 ?
O1 Mn O1W 89.77(6) 5_656 . ?
O1 Mn O1W 90.23(6) . . ?
N1 Mn O1W 89.36(5) . . ?
N1 Mn O1W 90.64(5) 5_656 . ?
O1W Mn O1W 180.0 5_656 . ?
Mn O1W H11 116.4(16) . . ?
Mn O1W H12 107.6(18) . . ?
H11 O1W H12 103(2) . . ?
C7 N1 C8 116.14(15) . . ?
C7 N1 Mn 121.09(12) . . ?
C8 N1 Mn 122.72(11) . . ?
C13 N2 C9 111.52(16) . . ?
C13 N2 C10 108.06(15) . . ?
C9 N2 C10 110.43(15) . . ?
C1 O1 Mn 127.24(12) . . ?
C11 O2 C12 109.65(18) . . ?
O1 C1 C6 122.64(17) . . ?
O1 C1 C2 118.92(18) . . ?
C6 C1 C2 118.42(18) . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 121.5(2) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 119.0(2) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.4(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 119.2(2) . . ?
C1 C6 C7 122.86(17) . . ?
C5 C6 C7 117.8(2) . . ?
N1 C7 C6 126.98(17) . . ?
N1 C7 H7 116.5 . . ?
C6 C7 H7 116.5 . . ?
N1 C8 C9 112.97(16) . . ?
N1 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
N1 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
N2 C9 C8 114.77(15) . . ?
N2 C9 H9A 108.6 . . ?
C8 C9 H9A 108.6 . . ?
N2 C9 H9B 108.6 . . ?
C8 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
N2 C10 C11 110.66(19) . . ?
N2 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
O2 C11 C10 112.4(2) . . ?
O2 C11 H11A 109.1 . . ?
C10 C11 H11A 109.1 . . ?
O2 C11 H11B 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
O2 C12 C13 111.8(2) . . ?
O2 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
O2 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
N2 C13 C12 110.0(2) . . ?
N2 C13 H13A 109.7 . . ?
C12 C13 H13A 109.7 . . ?
N2 C13 H13B 109.7 . . ?
C12 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Mn O1 C1 31.69(14) . . . . ?
N1 Mn O1 C1 -148.31(14) 5_656 . . . ?
O1W Mn O1 C1 -58.95(14) 5_656 . . . ?
O1W Mn O1 C1 121.05(14) . . . . ?
Mn O1 C1 C6 -21.9(2) . . . . ?
Mn O1 C1 C2 159.66(13) . . . . ?
O1 C1 C2 C3 -177.73(17) . . . . ?
C6 C1 C2 C3 3.7(3) . . . . ?
C1 C2 C3 C4 -1.3(3) . . . . ?
C2 C3 C4 C5 -2.2(4) . . . . ?
C3 C4 C5 C6 3.0(4) . . . . ?
O1 C1 C6 C5 178.67(18) . . . . ?
C2 C1 C6 C5 -2.9(3) . . . . ?
O1 C1 C6 C7 -6.0(3) . . . . ?
C2 C1 C6 C7 172.43(17) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
C4 C5 C6 C7 -176.0(2) . . . . ?
C8 N1 C7 C6 -174.04(18) . . . . ?
Mn N1 C7 C6 8.6(3) . . . . ?
C1 C6 C7 N1 11.8(3) . . . . ?
C5 C6 C7 N1 -172.9(2) . . . . ?
C7 N1 C8 C9 86.5(2) . . . . ?
Mn N1 C8 C9 -96.13(17) . . . . ?
C13 N2 C9 C8 74.8(2) . . . . ?
C10 N2 C9 C8 -165.02(17) . . . . ?
N1 C8 C9 N2 78.6(2) . . . . ?
C13 N2 C10 C11 -56.7(2) . . . . ?
C9 N2 C10 C11 -178.92(18) . . . . ?
C12 O2 C11 C10 -57.0(3) . . . . ?
N2 C10 C11 O2 57.7(2) . . . . ?
C11 O2 C12 C13 57.5(3) . . . . ?
C9 N2 C13 C12 178.75(18) . . . . ?
C10 N2 C13 C12 57.2(2) . . . . ?
O2 C12 C13 N2 -59.3(3) . . . . ?

_refine_diff_density_max         0.314
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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 1841248'
_audit_update_record             
;
2018-07-24 deposited with the CCDC.
2018-07-27 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         'C28 H42 Mn N4 O6, I3'
_chemical_formula_sum            'C28 H42 I3 Mn N4 O6'
_chemical_formula_weight         966.29

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'
I I -0.4742 1.8119 '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                   9.487(1)
_cell_length_b                   10.508(2)
_cell_length_c                   10.717(1)
_cell_angle_alpha                89.830(5)
_cell_angle_beta                 69.668(4)
_cell_angle_gamma                63.170(4)
_cell_volume                     878.7(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    268(2)
_cell_measurement_reflns_used    3580
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      27.81


_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.826
_exptl_crystal_F_000             470
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    3.054
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.423
_exptl_absorpt_correction_T_max  0.512
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_absorpt_special_details   
'Bruker (2009). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.'

_diffrn_ambient_temperature      268(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23930
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_av_R_equivalents  0.0681
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.210
_diffrn_reflns_theta_max         28.847
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4555
_reflns_number_gt                3252
_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    'SHELX97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep3 for Windows (Farrugia,1997)'
_computing_publication_material  'Wingx 2013.3 (Farrugia, 1999)'

_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)+(0.0830P)²+2.2665P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4555
_refine_ls_number_parameters     197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1725
_refine_ls_wR_factor_gt          0.1486
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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
Mn Mn 0.5000 1.0000 0.5000 0.0317(2) Uani 1 2 d S . P . .
I1 I 0.23629(7) 0.61966(5) 0.92328(4) 0.0709(2) Uani 1 1 d . . . . .
I2 I 0.0000 0.5000 1.0000 0.0560(2) Uani 1 2 d S . P . .
N1 N 0.5954(5) 0.8015(4) 0.3890(4) 0.0321(8) Uani 1 1 d . . . . .
N2 N 0.7003(5) 0.4680(4) 0.5515(4) 0.0354(8) Uani 1 1 d . . . . .
O1 O 0.4184(5) 1.0896(4) 0.3710(3) 0.0398(8) Uani 1 1 d . . . . .
O2 O 0.9764(5) 0.2235(4) 0.5781(4) 0.0518(10) Uani 1 1 d . . . . .
H20 H 0.835(10) 0.930(9) 0.402(9) 0.078 Uiso 1 1 d . U . . .
O3 O 0.7548(5) 0.9917(4) 0.3872(4) 0.0434(8) Uani 1 1 d . . . . .
C1 C 0.3865(6) 1.0401(5) 0.2761(4) 0.0345(10) Uani 1 1 d . . . . .
C2 C 0.2896(7) 1.1389(6) 0.2132(5) 0.0436(11) Uani 1 1 d . . . . .
H2 H 0.2491 1.2376 0.2384 0.052 Uiso 1 1 calc R U . . .
C3 C 0.2530(8) 1.0925(7) 0.1142(6) 0.0523(14) Uani 1 1 d . . . . .
H3 H 0.1870 1.1599 0.0740 0.063 Uiso 1 1 calc R U . . .
C4 C 0.3136(9) 0.9464(8) 0.0743(6) 0.0573(15) Uani 1 1 d . . . . .
H4 H 0.2876 0.9156 0.0081 0.069 Uiso 1 1 calc R U . . .
C5 C 0.4119(8) 0.8474(7) 0.1324(5) 0.0486(13) Uani 1 1 d . . . . .
H5 H 0.4547 0.7489 0.1037 0.058 Uiso 1 1 calc R U . . .
C6 C 0.4493(6) 0.8921(6) 0.2351(5) 0.0356(10) Uani 1 1 d . . . . .
C7 C 0.5561(6) 0.7817(5) 0.2898(5) 0.0360(10) Uani 1 1 d . . . . .
H7 H 0.6015 0.6861 0.2494 0.043 Uiso 1 1 calc R U . . .
C8 C 0.7112(6) 0.6676(5) 0.4221(5) 0.0339(9) Uani 1 1 d . . . . .
H8A H 0.7707 0.6897 0.4689 0.041 Uiso 1 1 calc R U . . .
H8B H 0.7960 0.5983 0.3396 0.041 Uiso 1 1 calc R U . . .
C9 C 0.6059(6) 0.6029(5) 0.5120(5) 0.0376(10) Uani 1 1 d . . . . .
H9A H 0.5224 0.6742 0.5936 0.045 Uiso 1 1 calc R U . . .
H9B H 0.5429 0.5868 0.4649 0.045 Uiso 1 1 calc R U . . .
C10 C 0.8271(7) 0.3495(5) 0.4380(5) 0.0399(10) Uani 1 1 d . . . . .
H10A H 0.9188 0.3701 0.3869 0.048 Uiso 1 1 calc R U . . .
H10B H 0.7743 0.3398 0.3782 0.048 Uiso 1 1 calc R U . . .
C11 C 0.8994(7) 0.2096(6) 0.4898(6) 0.0453(12) Uani 1 1 d . . . . .
H11A H 0.8084 0.1872 0.5380 0.054 Uiso 1 1 calc R U . . .
H11B H 0.9842 0.1307 0.4142 0.054 Uiso 1 1 calc R U . . .
C12 C 0.8523(8) 0.3402(7) 0.6912(6) 0.0514(13) Uani 1 1 d . . . . .
H12A H 0.9069 0.3488 0.7499 0.062 Uiso 1 1 calc R U . . .
H12B H 0.7617 0.3187 0.7431 0.062 Uiso 1 1 calc R U . . .
C13 C 0.7766(7) 0.4810(6) 0.6442(5) 0.0424(11) Uani 1 1 d . . . . .
H13A H 0.6898 0.5572 0.7215 0.051 Uiso 1 1 calc R U . . .
H13B H 0.8653 0.5069 0.5989 0.051 Uiso 1 1 calc R U . . .
C14 C 0.8178(9) 1.0031(9) 0.2487(7) 0.0656(18) Uani 1 1 d . . . . .
H14A H 0.8421 0.9187 0.1927 0.098 Uiso 1 1 calc R U . . .
H14B H 0.9208 1.0101 0.2272 0.098 Uiso 1 1 calc R U . . .
H14C H 0.7331 1.0882 0.2326 0.098 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
Mn O1 1.864(3) . ?
Mn O1 1.864(3) 2_676 ?
Mn N1 2.036(4) 2_676 ?
Mn N1 2.036(4) . ?
Mn O3 2.256(4) . ?
Mn O3 2.256(4) 2_676 ?
I1 I2 2.9221(6) . ?
I2 I1 2.9221(6) 2_567 ?
N1 C7 1.288(6) . ?
N1 C8 1.478(6) . ?
N2 C9 1.451(6) . ?
N2 C10 1.455(6) . ?
N2 C13 1.456(6) . ?
O1 C1 1.325(5) . ?
O2 C11 1.424(7) . ?
O2 C12 1.440(7) . ?
O3 C14 1.422(7) . ?
O3 H20 0.82(8) . ?
C1 C2 1.394(7) . ?
C1 C6 1.397(7) . ?
C2 C3 1.377(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.408(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.436(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.526(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.513(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.499(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
O1 Mn O1 180.0 . 2_676 ?
O1 Mn N1 89.76(15) . 2_676 ?
O1 Mn N1 90.24(15) 2_676 2_676 ?
O1 Mn N1 90.24(15) . . ?
O1 Mn N1 89.76(15) 2_676 . ?
N1 Mn N1 180.0(2) 2_676 . ?
O1 Mn O3 90.86(15) . . ?
O1 Mn O3 89.14(15) 2_676 . ?
N1 Mn O3 91.58(14) 2_676 . ?
N1 Mn O3 88.42(14) . . ?
O1 Mn O3 89.14(15) . 2_676 ?
O1 Mn O3 90.86(15) 2_676 2_676 ?
N1 Mn O3 88.42(14) 2_676 2_676 ?
N1 Mn O3 91.58(14) . 2_676 ?
O3 Mn O3 180.0 . 2_676 ?
I1 I2 I1 180.0 2_567 . ?
C7 N1 C8 115.1(4) . . ?
C7 N1 Mn 123.7(3) . . ?
C8 N1 Mn 121.2(3) . . ?
C9 N2 C10 113.9(4) . . ?
C9 N2 C13 114.6(4) . . ?
C10 N2 C13 110.3(4) . . ?
C1 O1 Mn 131.0(3) . . ?
C11 O2 C12 110.5(4) . . ?
C14 O3 Mn 125.0(4) . . ?
C14 O3 H20 108(6) . . ?
Mn O3 H20 115(6) . . ?
O1 C1 C2 118.8(5) . . ?
O1 C1 C6 122.3(4) . . ?
C2 C1 C6 118.8(4) . . ?
C3 C2 C1 120.9(5) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 120.4(5) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 119.8(5) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.9(5) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 119.1(5) . . ?
C1 C6 C7 123.0(4) . . ?
C5 C6 C7 117.9(5) . . ?
N1 C7 C6 126.7(4) . . ?
N1 C7 H7 116.6 . . ?
C6 C7 H7 116.6 . . ?
N1 C8 C9 109.1(4) . . ?
N1 C8 H8A 109.9 . . ?
C9 C8 H8A 109.9 . . ?
N1 C8 H8B 109.9 . . ?
C9 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
N2 C9 C8 116.6(4) . . ?
N2 C9 H9A 108.1 . . ?
C8 C9 H9A 108.1 . . ?
N2 C9 H9B 108.1 . . ?
C8 C9 H9B 108.1 . . ?
H9A C9 H9B 107.3 . . ?
N2 C10 C11 109.7(4) . . ?
N2 C10 H10A 109.7 . . ?
C11 C10 H10A 109.7 . . ?
N2 C10 H10B 109.7 . . ?
C11 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
O2 C11 C10 110.0(4) . . ?
O2 C11 H11A 109.7 . . ?
C10 C11 H11A 109.7 . . ?
O2 C11 H11B 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
O2 C12 C13 111.0(5) . . ?
O2 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
O2 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
N2 C13 C12 110.1(4) . . ?
N2 C13 H13A 109.6 . . ?
C12 C13 H13A 109.6 . . ?
N2 C13 H13B 109.6 . . ?
C12 C13 H13B 109.6 . . ?
H13A C13 H13B 108.2 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Mn O1 C1 -160.1(4) 2_676 . . . ?
N1 Mn O1 C1 19.9(4) . . . . ?
O3 Mn O1 C1 108.3(4) . . . . ?
O3 Mn O1 C1 -71.7(4) 2_676 . . . ?
Mn O1 C1 C2 165.5(4) . . . . ?
Mn O1 C1 C6 -15.8(7) . . . . ?
O1 C1 C2 C3 -179.9(5) . . . . ?
C6 C1 C2 C3 1.3(8) . . . . ?
C1 C2 C3 C4 -0.8(9) . . . . ?
C2 C3 C4 C5 -0.7(10) . . . . ?
C3 C4 C5 C6 1.5(10) . . . . ?
O1 C1 C6 C5 -179.2(5) . . . . ?
C2 C1 C6 C5 -0.5(7) . . . . ?
O1 C1 C6 C7 -1.4(7) . . . . ?
C2 C1 C6 C7 177.4(5) . . . . ?
C4 C5 C6 C1 -0.9(8) . . . . ?
C4 C5 C6 C7 -178.9(6) . . . . ?
C8 N1 C7 C6 -178.8(4) . . . . ?
Mn N1 C7 C6 3.8(7) . . . . ?
C1 C6 C7 N1 6.6(8) . . . . ?
C5 C6 C7 N1 -175.5(5) . . . . ?
C7 N1 C8 C9 -82.5(5) . . . . ?
Mn N1 C8 C9 94.9(4) . . . . ?
C10 N2 C9 C8 -59.8(6) . . . . ?
C13 N2 C9 C8 68.5(6) . . . . ?
N1 C8 C9 N2 178.4(4) . . . . ?
C9 N2 C10 C11 -171.8(4) . . . . ?
C13 N2 C10 C11 57.7(5) . . . . ?
C12 O2 C11 C10 59.4(6) . . . . ?
N2 C10 C11 O2 -59.1(6) . . . . ?
C11 O2 C12 C13 -58.6(6) . . . . ?
C9 N2 C13 C12 173.2(4) . . . . ?
C10 N2 C13 C12 -56.6(6) . . . . ?
O2 C12 C13 N2 56.8(6) . . . . ?

_refine_diff_density_max         1.906
_refine_diff_density_min         -1.757
_refine_diff_density_rms         0.192

