# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_b
_database_code_depnum_ccdc_archive 'CCDC 1442331'
_audit_update_record             
;
2015-12-14 deposited with the CCDC.
2016-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H21 I2 Mn N3 O2'
_chemical_formula_weight         560.07

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

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

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

_cell_length_a                   14.6223(10)
_cell_length_b                   16.5304(12)
_cell_length_c                   15.2077(11)
_cell_angle_alpha                90
_cell_angle_beta                 98.7810(10)
_cell_angle_gamma                90
_cell_volume                     3632.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    30784
_cell_measurement_theta_min      1.4
_cell_measurement_theta_max      27.5

_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.048
_exptl_crystal_F_000             2136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    4.133
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.759
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'XDS (Kabsch, 1993)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device       
;
AFC11 (Right): Eulerian 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            27041
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.800
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_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             6390
_reflns_number_gt                6149
_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       
;
CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+50.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6390
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0641
_refine_ls_wR_factor_ref         0.1756
_refine_ls_wR_factor_gt          0.1746
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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
Mn1A Mn 0.47234(9) 0.67395(8) 0.19694(8) 0.0232(3) Uani 1 1 d . . . . .
Mn1B Mn 0.52486(9) 0.13265(8) 0.28938(8) 0.0240(3) Uani 1 1 d . . . . .
I1A I 0.59695(3) 0.60097(3) 0.08372(3) 0.02228(18) Uani 1 1 d . . . . .
O1A O 0.4402(4) 0.7637(4) 0.0814(4) 0.0311(14) Uani 1 1 d . . . . .
O1B O 0.5443(4) 0.0238(3) 0.3802(4) 0.0253(12) Uani 1 1 d . . . . .
O2A O 0.5625(4) 0.7869(4) 0.2233(4) 0.0333(14) Uani 1 1 d . . . . .
O2B O 0.4274(4) 0.0296(4) 0.2303(4) 0.0280(13) Uani 1 1 d . . . . .
N1A N 0.4374(5) 0.5547(4) 0.2499(5) 0.0272(16) Uani 1 1 d . . . . .
N1B N 0.5690(5) 0.2589(4) 0.2691(5) 0.0242(15) Uani 1 1 d . . . . .
N2A N 0.3408(5) 0.6305(5) 0.1105(5) 0.0250(15) Uani 1 1 d . . . . .
H2AA H 0.2877 0.6504 0.1389 0.030 Uiso 1 1 calc R U . . .
N2B N 0.6556(5) 0.1560(4) 0.3896(5) 0.0248(15) Uani 1 1 d . . . . .
H2BB H 0.7096 0.1411 0.3597 0.030 Uiso 1 1 calc R U . . .
N3A N 0.5841(6) 0.6432(5) 0.3149(5) 0.0327(17) Uani 1 1 d . . . . .
H3AA H 0.6329 0.6119 0.2903 0.039 Uiso 1 1 calc R U . . .
N3B N 0.4202(5) 0.1878(5) 0.1778(5) 0.0281(16) Uani 1 1 d . . . . .
H3BB H 0.3708 0.2131 0.2075 0.034 Uiso 1 1 calc R U . . .
I1B I 0.65526(5) 0.07055(4) 0.16751(5) 0.0389(2) Uani 1 1 d . . . . .
I2A I 0.34224(4) 0.74559(4) 0.31359(5) 0.0366(2) Uani 1 1 d . . . . .
C2 C 0.6280(7) 0.7177(7) 0.3525(7) 0.045(3) Uani 1 1 d . . . . .
H2A H 0.6858 0.7044 0.3929 0.054 Uiso 1 1 calc R U . . .
H2B H 0.5860 0.7460 0.3877 0.054 Uiso 1 1 calc R U . . .
I2B I 0.40398(3) 0.18874(3) 0.41452(3) 0.02330(18) Uani 1 1 d . . . . .
C3 C 0.6494(7) 0.7715(6) 0.2802(7) 0.038(2) Uani 1 1 d . . . . .
H3A H 0.6772 0.8227 0.3051 0.046 Uiso 1 1 calc R U . . .
H3B H 0.6936 0.7448 0.2462 0.046 Uiso 1 1 calc R U . . .
C5 C 0.5688(7) 0.8359(6) 0.1458(7) 0.040(2) Uani 1 1 d . . . . .
H5A H 0.6088 0.8093 0.1073 0.048 Uiso 1 1 calc R U . . .
H5B H 0.5952 0.8896 0.1636 0.048 Uiso 1 1 calc R U . . .
C6 C 0.4735(8) 0.8442(6) 0.0981(7) 0.040(2) Uani 1 1 d . . . . .
H6A H 0.4343 0.8738 0.1350 0.048 Uiso 1 1 calc R U . . .
H6B H 0.4731 0.8740 0.0415 0.048 Uiso 1 1 calc R U . . .
C8 C 0.3492(6) 0.7570(7) 0.0309(7) 0.039(3) Uani 1 1 d . . . . .
H8A H 0.3468 0.7831 -0.0280 0.047 Uiso 1 1 calc R U . . .
H8B H 0.3029 0.7829 0.0628 0.047 Uiso 1 1 calc R U . . .
C9 C 0.3310(6) 0.6679(7) 0.0206(6) 0.038(2) Uani 1 1 d . . . . .
H9A H 0.2678 0.6586 -0.0116 0.045 Uiso 1 1 calc R U . . .
H9B H 0.3757 0.6431 -0.0142 0.045 Uiso 1 1 calc R U . . .
C11 C 0.3362(6) 0.5429(6) 0.1106(7) 0.035(2) Uani 1 1 d . . . . .
H11A H 0.3733 0.5211 0.0667 0.042 Uiso 1 1 calc R U . . .
H11B H 0.2712 0.5255 0.0927 0.042 Uiso 1 1 calc R U . . .
C12 C 0.3717(6) 0.5099(5) 0.2000(7) 0.034(2) Uani 1 1 d . . . . .
C14 C 0.4782(7) 0.5312(6) 0.3298(7) 0.035(2) Uani 1 1 d . . . . .
C15 C 0.4539(8) 0.4577(7) 0.3641(8) 0.048(3) Uani 1 1 d . . . . .
H15 H 0.4843 0.4393 0.4202 0.058 Uiso 1 1 calc R U . . .
C16 C 0.3856(9) 0.4122(6) 0.3160(11) 0.060(4) Uani 1 1 d . . . . .
H16 H 0.3662 0.3635 0.3406 0.072 Uiso 1 1 calc R U . . .
C17 C 0.3443(8) 0.4362(6) 0.2319(9) 0.046(3) Uani 1 1 d . . . . .
H17 H 0.2989 0.4035 0.1973 0.055 Uiso 1 1 calc R U . . .
C18 C 0.5466(8) 0.5891(7) 0.3778(6) 0.044(3) Uani 1 1 d . . . . .
H18A H 0.5163 0.6218 0.4197 0.053 Uiso 1 1 calc R U . . .
H18B H 0.5979 0.5585 0.4129 0.053 Uiso 1 1 calc R U . . .
C102 C 0.6586(6) 0.1029(5) 0.4680(6) 0.0280(19) Uani 1 1 d . . . . .
H10A H 0.6144 0.1225 0.5065 0.034 Uiso 1 1 calc R U . . .
H10B H 0.7214 0.1034 0.5031 0.034 Uiso 1 1 calc R U . . .
C103 C 0.6330(6) 0.0173(6) 0.4361(6) 0.0300(19) Uani 1 1 d . . . . .
H10C H 0.6799 -0.0046 0.4020 0.036 Uiso 1 1 calc R U . . .
H10D H 0.6289 -0.0188 0.4872 0.036 Uiso 1 1 calc R U . . .
C105 C 0.5048(6) -0.0502(5) 0.3459(6) 0.0303(19) Uani 1 1 d . . . . .
H10E H 0.4988 -0.0882 0.3950 0.036 Uiso 1 1 calc R U . . .
H10F H 0.5441 -0.0756 0.3060 0.036 Uiso 1 1 calc R U . . .
C106 C 0.4114(6) -0.0300(6) 0.2954(6) 0.032(2) Uani 1 1 d . . . . .
H10G H 0.3819 -0.0789 0.2658 0.038 Uiso 1 1 calc R U . . .
H10H H 0.3706 -0.0080 0.3359 0.038 Uiso 1 1 calc R U . . .
C108 C 0.3458(6) 0.0574(6) 0.1755(7) 0.035(2) Uani 1 1 d . . . . .
H10I H 0.3005 0.0773 0.2127 0.042 Uiso 1 1 calc R U . . .
H10J H 0.3169 0.0129 0.1374 0.042 Uiso 1 1 calc R U . . .
C109 C 0.3744(7) 0.1254(6) 0.1185(6) 0.032(2) Uani 1 1 d . . . . .
H10K H 0.4172 0.1047 0.0793 0.039 Uiso 1 1 calc R U . . .
H10L H 0.3193 0.1483 0.0808 0.039 Uiso 1 1 calc R U . . .
C111 C 0.4619(7) 0.2540(6) 0.1324(6) 0.033(2) Uani 1 1 d . . . . .
H11C H 0.4127 0.2919 0.1062 0.039 Uiso 1 1 calc R U . . .
H11D H 0.4915 0.2315 0.0835 0.039 Uiso 1 1 calc R U . . .
C112 C 0.5326(6) 0.2990(5) 0.1958(6) 0.0267(18) Uani 1 1 d . . . . .
C114 C 0.6343(6) 0.2924(5) 0.3294(6) 0.0250(17) Uani 1 1 d . . . . .
C115 C 0.6674(6) 0.3694(6) 0.3164(6) 0.0298(19) Uani 1 1 d . . . . .
H115 H 0.7135 0.3931 0.3595 0.036 Uiso 1 1 calc R U . . .
C116 C 0.6322(6) 0.4114(5) 0.2393(6) 0.0294(19) Uani 1 1 d . . . . .
H116 H 0.6559 0.4633 0.2279 0.035 Uiso 1 1 calc R U . . .
C117 C 0.5622(6) 0.3767(5) 0.1793(6) 0.0282(19) Uani 1 1 d . . . . .
H117 H 0.5349 0.4056 0.1279 0.034 Uiso 1 1 calc R U . . .
C118 C 0.6649(6) 0.2411(5) 0.4120(6) 0.0287(19) Uani 1 1 d . . . . .
H11E H 0.7302 0.2534 0.4361 0.034 Uiso 1 1 calc R U . . .
H11F H 0.6265 0.2542 0.4583 0.034 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
Mn1A N1A 2.218(7) . ?
Mn1A N2A 2.274(7) . ?
Mn1A O2A 2.285(6) . ?
Mn1A N3A 2.292(8) . ?
Mn1A O1A 2.293(6) . ?
Mn1A I1A 2.9493(14) . ?
Mn1A I2A 3.0329(15) . ?
Mn1B N1B 2.220(7) . ?
Mn1B O1B 2.260(6) . ?
Mn1B N2B 2.288(7) . ?
Mn1B N3B 2.293(7) . ?
Mn1B O2B 2.313(6) . ?
Mn1B I2B 2.9380(14) . ?
Mn1B I1B 3.0337(14) . ?
O1A C6 1.427(12) . ?
O1A C8 1.435(11) . ?
O1B C105 1.417(11) . ?
O1B C103 1.442(10) . ?
O2A C5 1.445(12) . ?
O2A C3 1.447(12) . ?
O2B C108 1.423(11) . ?
O2B C106 1.442(11) . ?
N1A C14 1.328(12) . ?
N1A C12 1.351(13) . ?
N1B C112 1.336(11) . ?
N1B C114 1.338(12) . ?
N2A C11 1.450(12) . ?
N2A C9 1.487(11) . ?
N2A H2AA 1.0000 . ?
N2B C118 1.449(11) . ?
N2B C102 1.476(10) . ?
N2B H2BB 1.0000 . ?
N3A C2 1.464(13) . ?
N3A C18 1.476(13) . ?
N3A H3AA 1.0000 . ?
N3B C109 1.462(12) . ?
N3B C111 1.476(11) . ?
N3B H3BB 1.0000 . ?
C2 C3 1.484(16) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 C6 1.477(16) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 C9 1.501(16) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C11 C12 1.483(15) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C17 1.393(14) . ?
C14 C15 1.390(14) . ?
C14 C18 1.492(16) . ?
C15 C16 1.369(19) . ?
C15 H15 0.9500 . ?
C16 C17 1.39(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C102 C103 1.524(13) . ?
C102 H10A 0.9900 . ?
C102 H10B 0.9900 . ?
C103 H10C 0.9900 . ?
C103 H10D 0.9900 . ?
C105 C106 1.500(13) . ?
C105 H10E 0.9900 . ?
C105 H10F 0.9900 . ?
C106 H10G 0.9900 . ?
C106 H10H 0.9900 . ?
C108 C109 1.516(14) . ?
C108 H10I 0.9900 . ?
C108 H10J 0.9900 . ?
C109 H10K 0.9900 . ?
C109 H10L 0.9900 . ?
C111 C112 1.498(14) . ?
C111 H11C 0.9900 . ?
C111 H11D 0.9900 . ?
C112 C117 1.391(12) . ?
C114 C115 1.387(13) . ?
C114 C118 1.525(12) . ?
C115 C116 1.392(13) . ?
C115 H115 0.9500 . ?
C116 C117 1.388(14) . ?
C116 H116 0.9500 . ?
C117 H117 0.9500 . ?
C118 H11E 0.9900 . ?
C118 H11F 0.9900 . ?

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
N1A Mn1A N2A 73.0(3) . . ?
N1A Mn1A O2A 145.2(3) . . ?
N2A Mn1A O2A 140.7(3) . . ?
N1A Mn1A N3A 72.3(3) . . ?
N2A Mn1A N3A 145.3(3) . . ?
O2A Mn1A N3A 73.8(3) . . ?
N1A Mn1A O1A 145.2(3) . . ?
N2A Mn1A O1A 72.8(3) . . ?
O2A Mn1A O1A 69.6(2) . . ?
N3A Mn1A O1A 141.4(3) . . ?
N1A Mn1A I1A 92.62(18) . . ?
N2A Mn1A I1A 94.40(18) . . ?
O2A Mn1A I1A 92.59(17) . . ?
N3A Mn1A I1A 86.3(2) . . ?
O1A Mn1A I1A 83.66(16) . . ?
N1A Mn1A I2A 86.25(18) . . ?
N2A Mn1A I2A 84.88(18) . . ?
O2A Mn1A I2A 88.58(16) . . ?
N3A Mn1A I2A 93.7(2) . . ?
O1A Mn1A I2A 97.03(16) . . ?
I1A Mn1A I2A 178.80(5) . . ?
N1B Mn1B O1B 145.2(3) . . ?
N1B Mn1B N2B 72.7(3) . . ?
O1B Mn1B N2B 73.3(2) . . ?
N1B Mn1B N3B 72.5(3) . . ?
O1B Mn1B N3B 140.9(3) . . ?
N2B Mn1B N3B 145.2(3) . . ?
N1B Mn1B O2B 144.4(2) . . ?
O1B Mn1B O2B 70.3(2) . . ?
N2B Mn1B O2B 141.8(2) . . ?
N3B Mn1B O2B 72.7(2) . . ?
N1B Mn1B I2B 90.54(18) . . ?
O1B Mn1B I2B 83.54(15) . . ?
N2B Mn1B I2B 92.26(18) . . ?
N3B Mn1B I2B 87.37(19) . . ?
O2B Mn1B I2B 95.07(16) . . ?
N1B Mn1B I1B 90.59(18) . . ?
O1B Mn1B I1B 94.11(15) . . ?
N2B Mn1B I1B 85.69(18) . . ?
N3B Mn1B I1B 95.36(19) . . ?
O2B Mn1B I1B 85.45(16) . . ?
I2B Mn1B I1B 177.25(5) . . ?
C6 O1A C8 115.4(8) . . ?
C6 O1A Mn1A 116.3(6) . . ?
C8 O1A Mn1A 115.1(5) . . ?
C105 O1B C103 115.6(6) . . ?
C105 O1B Mn1B 117.1(5) . . ?
C103 O1B Mn1B 115.9(5) . . ?
C5 O2A C3 115.3(7) . . ?
C5 O2A Mn1A 114.9(6) . . ?
C3 O2A Mn1A 113.0(5) . . ?
C108 O2B C106 114.4(7) . . ?
C108 O2B Mn1B 113.7(5) . . ?
C106 O2B Mn1B 113.1(5) . . ?
C14 N1A C12 122.3(8) . . ?
C14 N1A Mn1A 119.7(7) . . ?
C12 N1A Mn1A 117.9(6) . . ?
C112 N1B C114 121.3(8) . . ?
C112 N1B Mn1B 119.6(6) . . ?
C114 N1B Mn1B 119.1(6) . . ?
C11 N2A C9 114.7(8) . . ?
C11 N2A Mn1A 110.5(6) . . ?
C9 N2A Mn1A 110.8(6) . . ?
C11 N2A H2AA 106.8 . . ?
C9 N2A H2AA 106.8 . . ?
Mn1A N2A H2AA 106.8 . . ?
C118 N2B C102 113.4(7) . . ?
C118 N2B Mn1B 111.1(5) . . ?
C102 N2B Mn1B 110.9(5) . . ?
C118 N2B H2BB 107.0 . . ?
C102 N2B H2BB 107.0 . . ?
Mn1B N2B H2BB 107.0 . . ?
C2 N3A C18 116.2(8) . . ?
C2 N3A Mn1A 109.7(6) . . ?
C18 N3A Mn1A 110.5(6) . . ?
C2 N3A H3AA 106.6 . . ?
C18 N3A H3AA 106.6 . . ?
Mn1A N3A H3AA 106.6 . . ?
C109 N3B C111 114.7(7) . . ?
C109 N3B Mn1B 111.5(6) . . ?
C111 N3B Mn1B 111.4(6) . . ?
C109 N3B H3BB 106.2 . . ?
C111 N3B H3BB 106.2 . . ?
Mn1B N3B H3BB 106.2 . . ?
N3A C2 C3 110.1(8) . . ?
N3A C2 H2A 109.6 . . ?
C3 C2 H2A 109.6 . . ?
N3A C2 H2B 109.6 . . ?
C3 C2 H2B 109.6 . . ?
H2A C2 H2B 108.2 . . ?
O2A C3 C2 106.5(8) . . ?
O2A C3 H3A 110.4 . . ?
C2 C3 H3A 110.4 . . ?
O2A C3 H3B 110.4 . . ?
C2 C3 H3B 110.4 . . ?
H3A C3 H3B 108.6 . . ?
O2A C5 C6 106.3(8) . . ?
O2A C5 H5A 110.5 . . ?
C6 C5 H5A 110.5 . . ?
O2A C5 H5B 110.5 . . ?
C6 C5 H5B 110.5 . . ?
H5A C5 H5B 108.7 . . ?
O1A C6 C5 105.7(8) . . ?
O1A C6 H6A 110.6 . . ?
C5 C6 H6A 110.6 . . ?
O1A C6 H6B 110.6 . . ?
C5 C6 H6B 110.6 . . ?
H6A C6 H6B 108.7 . . ?
O1A C8 C9 105.5(7) . . ?
O1A C8 H8A 110.6 . . ?
C9 C8 H8A 110.6 . . ?
O1A C8 H8B 110.6 . . ?
C9 C8 H8B 110.6 . . ?
H8A C8 H8B 108.8 . . ?
N2A C9 C8 108.7(8) . . ?
N2A C9 H9A 109.9 . . ?
C8 C9 H9A 109.9 . . ?
N2A C9 H9B 109.9 . . ?
C8 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
N2A C11 C12 111.0(8) . . ?
N2A C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
N2A C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N1A C12 C17 120.1(11) . . ?
N1A C12 C11 115.6(8) . . ?
C17 C12 C11 124.2(10) . . ?
N1A C14 C15 119.7(11) . . ?
N1A C14 C18 115.8(8) . . ?
C15 C14 C18 124.6(10) . . ?
C16 C15 C14 119.1(11) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C17 121.0(10) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C16 C17 C12 117.6(12) . . ?
C16 C17 H17 121.2 . . ?
C12 C17 H17 121.2 . . ?
N3A C18 C14 111.0(8) . . ?
N3A C18 H18A 109.4 . . ?
C14 C18 H18A 109.4 . . ?
N3A C18 H18B 109.4 . . ?
C14 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
N2B C102 C103 108.6(7) . . ?
N2B C102 H10A 110.0 . . ?
C103 C102 H10A 110.0 . . ?
N2B C102 H10B 110.0 . . ?
C103 C102 H10B 110.0 . . ?
H10A C102 H10B 108.4 . . ?
O1B C103 C102 105.9(7) . . ?
O1B C103 H10C 110.5 . . ?
C102 C103 H10C 110.5 . . ?
O1B C103 H10D 110.5 . . ?
C102 C103 H10D 110.5 . . ?
H10C C103 H10D 108.7 . . ?
O1B C105 C106 106.6(7) . . ?
O1B C105 H10E 110.4 . . ?
C106 C105 H10E 110.4 . . ?
O1B C105 H10F 110.4 . . ?
C106 C105 H10F 110.4 . . ?
H10E C105 H10F 108.6 . . ?
O2B C106 C105 105.8(7) . . ?
O2B C106 H10G 110.6 . . ?
C105 C106 H10G 110.6 . . ?
O2B C106 H10H 110.6 . . ?
C105 C106 H10H 110.6 . . ?
H10G C106 H10H 108.7 . . ?
O2B C108 C109 107.1(7) . . ?
O2B C108 H10I 110.3 . . ?
C109 C108 H10I 110.3 . . ?
O2B C108 H10J 110.3 . . ?
C109 C108 H10J 110.3 . . ?
H10I C108 H10J 108.6 . . ?
N3B C109 C108 108.1(7) . . ?
N3B C109 H10K 110.1 . . ?
C108 C109 H10K 110.1 . . ?
N3B C109 H10L 110.1 . . ?
C108 C109 H10L 110.1 . . ?
H10K C109 H10L 108.4 . . ?
N3B C111 C112 111.2(7) . . ?
N3B C111 H11C 109.4 . . ?
C112 C111 H11C 109.4 . . ?
N3B C111 H11D 109.4 . . ?
C112 C111 H11D 109.4 . . ?
H11C C111 H11D 108.0 . . ?
N1B C112 C117 120.8(9) . . ?
N1B C112 C111 116.1(8) . . ?
C117 C112 C111 123.1(8) . . ?
N1B C114 C115 120.7(8) . . ?
N1B C114 C118 115.1(8) . . ?
C115 C114 C118 124.2(8) . . ?
C114 C115 C116 119.1(9) . . ?
C114 C115 H115 120.5 . . ?
C116 C115 H115 120.5 . . ?
C117 C116 C115 119.2(8) . . ?
C117 C116 H116 120.4 . . ?
C115 C116 H116 120.4 . . ?
C116 C117 C112 118.9(8) . . ?
C116 C117 H117 120.6 . . ?
C112 C117 H117 120.6 . . ?
N2B C118 C114 109.9(7) . . ?
N2B C118 H11E 109.7 . . ?
C114 C118 H11E 109.7 . . ?
N2B C118 H11F 109.7 . . ?
C114 C118 H11F 109.7 . . ?
H11E C118 H11F 108.2 . . ?

_refine_diff_density_max         5.819
_refine_diff_density_min         -2.745
_refine_diff_density_rms         0.289


_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# 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_b
_database_code_depnum_ccdc_archive 'CCDC 1442332'
_audit_update_record             
;
2015-12-14 deposited with the CCDC.
2016-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H21 Mn N9 O2'
_chemical_formula_weight         390.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.8283(6)
_cell_length_b                   12.8416(7)
_cell_length_c                   13.4703(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.300(2)
_cell_angle_gamma                90
_cell_volume                     1672.70(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9510
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      27.1

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_F_000             812
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.819
_shelx_estimated_absorpt_T_min   0.887
_shelx_estimated_absorpt_T_max   0.923
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-III CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            116071
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.375
_diffrn_reflns_theta_max         27.173
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3720
_reflns_number_gt                3266
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0265P)²+0.8742P] 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         3720
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0608
_refine_ls_wR_factor_gt          0.0578
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.81284(2) 0.71267(2) 0.56123(2) 0.01074(6) Uani 1 1 d . . . . .
N1 N 0.87387(11) 0.84519(8) 0.47516(8) 0.0125(2) Uani 1 1 d . . . . .
N2 N 1.04888(11) 0.70495(9) 0.56997(8) 0.0137(2) Uani 1 1 d . . . . .
H2C H 1.0909 0.7529 0.6255 0.016 Uiso 1 1 calc R U . . .
N3 N 0.61837(12) 0.81254(9) 0.51394(8) 0.0135(2) Uani 1 1 d . . . . .
H3C H 0.5689 0.7842 0.4482 0.016 Uiso 1 1 calc R U . . .
N4 N 0.85768(13) 0.80126(10) 0.70613(9) 0.0191(3) Uani 1 1 d . . . . .
N5 N 0.86078(12) 0.75664(10) 0.78371(9) 0.0182(3) Uani 1 1 d . . . . .
N6 N 0.86390(14) 0.71280(13) 0.86040(10) 0.0311(3) Uani 1 1 d . . . . .
N7 N 0.74767(13) 0.62879(9) 0.41559(9) 0.0189(3) Uani 1 1 d . . . . .
N8 N 0.74848(12) 0.67075(9) 0.33686(9) 0.0161(2) Uani 1 1 d . . . . .
N9 N 0.75144(16) 0.71067(10) 0.25922(10) 0.0278(3) Uani 1 1 d . . . . .
O2 O 0.64080(9) 0.63965(7) 0.63752(7) 0.0145(2) Uani 1 1 d . . . . .
O1 O 0.88448(9) 0.55208(7) 0.62644(7) 0.0145(2) Uani 1 1 d . . . . .
C1 C 0.64887(15) 0.52853(11) 0.63375(11) 0.0173(3) Uani 1 1 d . . . . .
H1A H 0.6300 0.5039 0.5630 0.021 Uiso 1 1 calc R U . . .
H1B H 0.5808 0.4964 0.6704 0.021 Uiso 1 1 calc R U . . .
C2 C 0.79383(15) 0.50077(11) 0.68327(11) 0.0176(3) Uani 1 1 d . . . . .
H2A H 0.8122 0.5248 0.7543 0.021 Uiso 1 1 calc R U . . .
H2B H 0.8075 0.4244 0.6823 0.021 Uiso 1 1 calc R U . . .
C3 C 1.02843(14) 0.55127(11) 0.67203(10) 0.0170(3) Uani 1 1 d . . . . .
H3A H 1.0606 0.4790 0.6871 0.020 Uiso 1 1 calc R U . . .
H3B H 1.0433 0.5915 0.7357 0.020 Uiso 1 1 calc R U . . .
C4 C 1.10633(14) 0.60053(11) 0.59673(11) 0.0166(3) Uani 1 1 d . . . . .
H4A H 1.2057 0.6061 0.6265 0.020 Uiso 1 1 calc R U . . .
H4B H 1.0972 0.5567 0.5354 0.020 Uiso 1 1 calc R U . . .
C5 C 1.08332(14) 0.74727(12) 0.47599(11) 0.0179(3) Uani 1 1 d . . . . .
H5A H 1.0699 0.6927 0.4232 0.021 Uiso 1 1 calc R U . . .
H5B H 1.1817 0.7686 0.4876 0.021 Uiso 1 1 calc R U . . .
C6 C 0.99295(14) 0.84002(10) 0.44034(10) 0.0140(3) Uani 1 1 d . . . . .
C7 C 0.78376(14) 0.92208(10) 0.44646(10) 0.0138(3) Uani 1 1 d . . . . .
C8 C 0.65624(14) 0.92038(11) 0.49541(11) 0.0167(3) Uani 1 1 d . . . . .
H8A H 0.6750 0.9590 0.5600 0.020 Uiso 1 1 calc R U . . .
H8B H 0.5785 0.9550 0.4507 0.020 Uiso 1 1 calc R U . . .
C9 C 0.52549(14) 0.79887(11) 0.58755(10) 0.0153(3) Uani 1 1 d . . . . .
H9A H 0.4351 0.8322 0.5623 0.018 Uiso 1 1 calc R U . . .
H9B H 0.5663 0.8317 0.6526 0.018 Uiso 1 1 calc R U . . .
C10 C 0.50621(14) 0.68347(11) 0.60215(11) 0.0169(3) Uani 1 1 d . . . . .
H10A H 0.4453 0.6715 0.6521 0.020 Uiso 1 1 calc R U . . .
H10B H 0.4634 0.6507 0.5376 0.020 Uiso 1 1 calc R U . . .
C11 C 0.81066(15) 0.99932(11) 0.38091(10) 0.0169(3) Uani 1 1 d . . . . .
H11A H 0.7458 1.0535 0.3607 0.020 Uiso 1 1 calc R U . . .
C12 C 0.93490(15) 0.99565(11) 0.34536(11) 0.0193(3) Uani 1 1 d . . . . .
H12A H 0.9564 1.0482 0.3010 0.023 Uiso 1 1 calc R U . . .
C13 C 1.02749(15) 0.91509(11) 0.37473(10) 0.0180(3) Uani 1 1 d . . . . .
H13A H 1.1125 0.9113 0.3506 0.022 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
Mn1 N1 2.2020(11) . ?
Mn1 N7 2.2293(12) . ?
Mn1 N4 2.2339(12) . ?
Mn1 N3 2.2953(11) . ?
Mn1 O1 2.3019(9) . ?
Mn1 N2 2.3040(11) . ?
Mn1 O2 2.3271(10) . ?
N1 C7 1.3366(17) . ?
N1 C6 1.3381(17) . ?
N2 C5 1.4716(17) . ?
N2 C4 1.4744(17) . ?
N2 H2C 1.0000 . ?
N3 C8 1.4668(17) . ?
N3 C9 1.4734(17) . ?
N3 H3C 1.0000 . ?
N4 N5 1.1874(17) . ?
N5 N6 1.1720(18) . ?
N7 N8 1.1909(17) . ?
N8 N9 1.1697(18) . ?
O2 C1 1.4306(16) . ?
O2 C10 1.4381(16) . ?
O1 C2 1.4345(16) . ?
O1 C3 1.4381(16) . ?
C1 C2 1.504(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.514(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.512(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C13 1.3903(19) . ?
C7 C11 1.3845(19) . ?
C7 C8 1.5170(19) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5112(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.390(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.388(2) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?

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
N1 Mn1 N7 88.42(4) . . ?
N1 Mn1 N4 92.10(4) . . ?
N7 Mn1 N4 174.68(5) . . ?
N1 Mn1 N3 73.37(4) . . ?
N7 Mn1 N3 86.09(4) . . ?
N4 Mn1 N3 88.99(4) . . ?
N1 Mn1 O1 143.10(4) . . ?
N7 Mn1 O1 85.59(4) . . ?
N4 Mn1 O1 97.11(4) . . ?
N3 Mn1 O1 142.11(4) . . ?
N1 Mn1 N2 72.15(4) . . ?
N7 Mn1 N2 98.76(4) . . ?
N4 Mn1 N2 86.43(4) . . ?
N3 Mn1 N2 144.99(4) . . ?
O1 Mn1 N2 72.87(4) . . ?
N1 Mn1 O2 146.28(4) . . ?
N7 Mn1 O2 94.41(4) . . ?
N4 Mn1 O2 82.23(4) . . ?
N3 Mn1 O2 73.32(4) . . ?
O1 Mn1 O2 70.57(3) . . ?
N2 Mn1 O2 139.87(4) . . ?
C7 N1 C6 120.74(12) . . ?
C7 N1 Mn1 119.63(9) . . ?
C6 N1 Mn1 118.94(9) . . ?
C5 N2 C4 114.16(11) . . ?
C5 N2 Mn1 108.94(8) . . ?
C4 N2 Mn1 112.93(8) . . ?
C5 N2 H2C 106.8 . . ?
C4 N2 H2C 106.8 . . ?
Mn1 N2 H2C 106.8 . . ?
C8 N3 C9 115.70(11) . . ?
C8 N3 Mn1 110.53(8) . . ?
C9 N3 Mn1 109.38(8) . . ?
C8 N3 H3C 106.9 . . ?
C9 N3 H3C 106.9 . . ?
Mn1 N3 H3C 106.9 . . ?
N5 N4 Mn1 119.55(10) . . ?
N6 N5 N4 179.85(18) . . ?
N8 N7 Mn1 121.23(10) . . ?
N9 N8 N7 178.64(15) . . ?
C1 O2 C10 115.60(10) . . ?
C1 O2 Mn1 109.69(8) . . ?
C10 O2 Mn1 113.20(8) . . ?
C2 O1 C3 115.23(10) . . ?
C2 O1 Mn1 115.99(8) . . ?
C3 O1 Mn1 112.33(8) . . ?
O2 C1 C2 105.95(11) . . ?
O2 C1 H1A 110.5 . . ?
C2 C1 H1A 110.5 . . ?
O2 C1 H1B 110.5 . . ?
C2 C1 H1B 110.5 . . ?
H1A C1 H1B 108.7 . . ?
O1 C2 C1 106.49(11) . . ?
O1 C2 H2A 110.4 . . ?
C1 C2 H2A 110.4 . . ?
O1 C2 H2B 110.4 . . ?
C1 C2 H2B 110.4 . . ?
H2A C2 H2B 108.6 . . ?
O1 C3 C4 106.71(10) . . ?
O1 C3 H3A 110.4 . . ?
C4 C3 H3A 110.4 . . ?
O1 C3 H3B 110.4 . . ?
C4 C3 H3B 110.4 . . ?
H3A C3 H3B 108.6 . . ?
N2 C4 C3 109.05(11) . . ?
N2 C4 H4A 109.9 . . ?
C3 C4 H4A 109.9 . . ?
N2 C4 H4B 109.9 . . ?
C3 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
N2 C5 C6 110.60(11) . . ?
N2 C5 H5A 109.5 . . ?
C6 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
N1 C6 C13 121.11(13) . . ?
N1 C6 C5 115.39(12) . . ?
C13 C6 C5 123.49(12) . . ?
N1 C7 C11 121.43(13) . . ?
N1 C7 C8 114.83(12) . . ?
C11 C7 C8 123.67(12) . . ?
N3 C8 C7 110.00(11) . . ?
N3 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
N3 C8 H8B 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
N3 C9 C10 108.16(11) . . ?
N3 C9 H9A 110.1 . . ?
C10 C9 H9A 110.1 . . ?
N3 C9 H9B 110.1 . . ?
C10 C9 H9B 110.1 . . ?
H9A C9 H9B 108.4 . . ?
O2 C10 C9 107.31(11) . . ?
O2 C10 H10A 110.3 . . ?
C9 C10 H10A 110.3 . . ?
O2 C10 H10B 110.3 . . ?
C9 C10 H10B 110.3 . . ?
H10A C10 H10B 108.5 . . ?
C7 C11 C12 118.37(13) . . ?
C7 C11 H11A 120.8 . . ?
C12 C11 H11A 120.8 . . ?
C13 C12 C11 119.92(13) . . ?
C13 C12 H12A 120.0 . . ?
C11 C12 H12A 120.0 . . ?
C12 C13 C6 118.42(13) . . ?
C12 C13 H13A 120.8 . . ?
C6 C13 H13A 120.8 . . ?

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
C10 O2 C1 C2 -174.58(11) . . . . ?
Mn1 O2 C1 C2 55.97(11) . . . . ?
C3 O1 C2 C1 169.08(11) . . . . ?
Mn1 O1 C2 C1 34.90(13) . . . . ?
O2 C1 C2 O1 -59.10(13) . . . . ?
C2 O1 C3 C4 175.26(11) . . . . ?
Mn1 O1 C3 C4 -48.91(12) . . . . ?
C5 N2 C4 C3 -161.64(11) . . . . ?
Mn1 N2 C4 C3 -36.47(13) . . . . ?
O1 C3 C4 N2 55.77(14) . . . . ?
C4 N2 C5 C6 165.72(11) . . . . ?
Mn1 N2 C5 C6 38.47(13) . . . . ?
C7 N1 C6 C13 1.02(19) . . . . ?
Mn1 N1 C6 C13 171.49(10) . . . . ?
C7 N1 C6 C5 -178.05(12) . . . . ?
Mn1 N1 C6 C5 -7.57(15) . . . . ?
N2 C5 C6 N1 -22.00(16) . . . . ?
N2 C5 C6 C13 158.96(12) . . . . ?
C6 N1 C7 C11 -0.66(19) . . . . ?
Mn1 N1 C7 C11 -171.07(10) . . . . ?
C6 N1 C7 C8 -177.56(12) . . . . ?
Mn1 N1 C7 C8 12.03(15) . . . . ?
C9 N3 C8 C7 161.98(11) . . . . ?
Mn1 N3 C8 C7 36.99(13) . . . . ?
N1 C7 C8 N3 -33.02(16) . . . . ?
C11 C7 C8 N3 150.16(13) . . . . ?
C8 N3 C9 C10 -176.11(11) . . . . ?
Mn1 N3 C9 C10 -50.52(12) . . . . ?
C1 O2 C10 C9 -166.12(11) . . . . ?
Mn1 O2 C10 C9 -38.40(12) . . . . ?
N3 C9 C10 O2 59.02(14) . . . . ?
N1 C7 C11 C12 -0.3(2) . . . . ?
C8 C7 C11 C12 176.35(13) . . . . ?
C7 C11 C12 C13 0.8(2) . . . . ?
C11 C12 C13 C6 -0.5(2) . . . . ?
N1 C6 C13 C12 -0.4(2) . . . . ?
C5 C6 C13 C12 178.56(13) . . . . ?

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
N3 H3C N6 1.00 2.15 2.9646(18) 137.8 4_575
C11 H11A N9 0.95 2.59 3.2999(19) 131.9 2_655

_refine_diff_density_max         0.236
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_b
_database_code_depnum_ccdc_archive 'CCDC 1442333'
_audit_update_record             
;
2015-12-14 deposited with the CCDC.
2016-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H21 Mn N5 O2 S2'
_chemical_formula_weight         422.43

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      triclinic
_space_group_IT_number           1
_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'

_cell_length_a                   10.1382(7)
_cell_length_b                   11.3567(8)
_cell_length_c                   14.0782(10)
_cell_angle_alpha                103.348(2)
_cell_angle_beta                 110.850(2)
_cell_angle_gamma                101.570(2)
_cell_volume                     1400.79(17)
_cell_formula_units_Z            3
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    16416
_cell_measurement_theta_min      1.6
_cell_measurement_theta_max      27.5

_exptl_crystal_description       cube
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_F_000             657
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.949
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.834
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'XDS (Kabsch, 1993)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14537
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.640
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             8526
_reflns_number_gt                8501
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_max     0.981
_reflns_Friedel_fraction_full    0.981

_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       
;
CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion 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)+(0.1250P)²+2.3000P] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.54(3)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         8526
_refine_ls_number_parameters     677
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0680
_refine_ls_wR_factor_ref         0.1757
_refine_ls_wR_factor_gt          0.1756
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.113
_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
Mn1A Mn 0.55462(11) 0.40173(10) 0.77031(9) 0.0216(3) Uani 1 1 d . . . . .
Mn1C Mn 0.89664(10) 0.67590(9) 0.49311(8) 0.0174(3) Uani 1 1 d . . . . .
Mn1B Mn 0.21660(12) 0.02944(10) 0.14916(9) 0.0215(3) Uani 1 1 d . . . . .
N1A N 0.5621(7) 0.3765(6) 0.9219(5) 0.0218(14) Uani 1 1 d . . . . .
N1C N 0.8719(7) 0.6846(6) 0.3310(5) 0.0210(13) Uani 1 1 d . . . . .
N1B N 0.2541(7) 0.0452(6) 0.0066(5) 0.0215(13) Uani 1 1 d . . . . .
O1A O 0.4648(7) 0.5022(6) 0.6488(5) 0.0355(15) Uani 1 1 d . . . . .
O1C O 0.9937(6) 0.5886(6) 0.6217(4) 0.0278(13) Uani 1 1 d . . . . .
O1B O 0.2647(7) -0.0626(6) 0.2822(5) 0.0304(14) Uani 1 1 d . . . . .
N2A N 0.4848(7) 0.5633(6) 0.8524(6) 0.0243(14) Uani 1 1 d . . . . .
H2AA H 0.5780 0.6353 0.9009 0.029 Uiso 1 1 calc R U . . .
N2C N 0.9511(7) 0.5035(7) 0.4105(5) 0.0221(13) Uani 1 1 d . . . . .
H2CA H 0.8553 0.4327 0.3676 0.026 Uiso 1 1 calc R U . . .
N2B N 0.3051(7) -0.1336(6) 0.0972(6) 0.0234(14) Uani 1 1 d . . . . .
H2BA H 0.2176 -0.2089 0.0451 0.028 Uiso 1 1 calc R U . . .
O2A O 0.6264(7) 0.3443(6) 0.6324(5) 0.0324(14) Uani 1 1 d . . . . .
O2C O 0.8423(6) 0.7498(6) 0.6372(4) 0.0279(13) Uani 1 1 d . . . . .
O2B O 0.0993(7) 0.0925(6) 0.2569(5) 0.0299(13) Uani 1 1 d . . . . .
N3A N 0.6342(7) 0.2250(6) 0.7856(5) 0.0233(14) Uani 1 1 d . . . . .
H3AA H 0.5440 0.1482 0.7492 0.028 Uiso 1 1 calc R U . . .
N3C N 0.8194(7) 0.8479(6) 0.4743(5) 0.0232(14) Uani 1 1 d . . . . .
H3CA H 0.9101 0.9236 0.5046 0.028 Uiso 1 1 calc R U . . .
N3B N 0.1473(7) 0.2007(6) 0.1122(6) 0.0258(15) Uani 1 1 d . . . . .
H3BA H 0.2370 0.2777 0.1543 0.031 Uiso 1 1 calc R U . . .
N4A N 0.7906(7) 0.5276(7) 0.8619(5) 0.0247(15) Uani 1 1 d . . . . .
N4C N 1.1267(8) 0.8024(7) 0.5641(7) 0.0314(17) Uani 1 1 d . . . . .
N4B N 0.4387(8) 0.1633(7) 0.2569(6) 0.0319(17) Uani 1 1 d . . . . .
N5A N 0.3264(8) 0.2681(8) 0.6788(7) 0.0356(18) Uani 1 1 d . . . . .
N5C N 0.6605(7) 0.5513(6) 0.4075(5) 0.0233(15) Uani 1 1 d . . . . .
N5B N -0.0068(8) -0.1030(7) 0.0396(7) 0.0340(18) Uani 1 1 d . . . . .
C102 C 0.7242(10) 0.2129(9) 0.7238(8) 0.034(2) Uani 1 1 d . . . . .
H10A H 0.7438 0.1300 0.7160 0.040 Uiso 1 1 calc R U . . .
H10B H 0.8209 0.2813 0.7632 0.040 Uiso 1 1 calc R U . . .
C103 C 0.6452(11) 0.2219(9) 0.6144(7) 0.037(2) Uani 1 1 d . . . . .
H10C H 0.7049 0.2120 0.5724 0.044 Uiso 1 1 calc R U . . .
H10D H 0.5476 0.1547 0.5743 0.044 Uiso 1 1 calc R U . . .
C105 C 0.5336(12) 0.3641(10) 0.5354(7) 0.042(2) Uani 1 1 d . . . . .
H10E H 0.4343 0.2992 0.5008 0.050 Uiso 1 1 calc R U . . .
H10F H 0.5792 0.3564 0.4836 0.050 Uiso 1 1 calc R U . . .
C106 C 0.5196(12) 0.4938(10) 0.5666(8) 0.041(2) Uani 1 1 d . . . . .
H10G H 0.6173 0.5592 0.5947 0.049 Uiso 1 1 calc R U . . .
H10H H 0.4496 0.5078 0.5035 0.049 Uiso 1 1 calc R U . . .
C108 C 0.4570(10) 0.6249(9) 0.6946(7) 0.035(2) Uani 1 1 d . . . . .
H10I H 0.3927 0.6522 0.6381 0.042 Uiso 1 1 calc R U . . .
H10J H 0.5572 0.6885 0.7314 0.042 Uiso 1 1 calc R U . . .
C109 C 0.3921(10) 0.6114(8) 0.7746(8) 0.033(2) Uani 1 1 d . . . . .
H10K H 0.3884 0.6950 0.8122 0.039 Uiso 1 1 calc R U . . .
H10L H 0.2896 0.5516 0.7364 0.039 Uiso 1 1 calc R U . . .
C111 C 0.4182(10) 0.5234(9) 0.9215(8) 0.032(2) Uani 1 1 d . . . . .
H11D H 0.3114 0.4758 0.8778 0.039 Uiso 1 1 calc R U . . .
H11E H 0.4271 0.5992 0.9777 0.039 Uiso 1 1 calc R U . . .
C112 C 0.4966(9) 0.4400(8) 0.9734(7) 0.0266(18) Uani 1 1 d . . . . .
C114 C 0.6275(9) 0.2969(7) 0.9615(6) 0.0226(16) Uani 1 1 d . . . . .
C115 C 0.6338(11) 0.2782(9) 1.0571(8) 0.038(2) Uani 1 1 d . . . . .
H11A H 0.6836 0.2229 1.0849 0.046 Uiso 1 1 calc R U . . .
C116 C 0.5649(13) 0.3432(11) 1.1101(8) 0.046(3) Uani 1 1 d . . . . .
H11B H 0.5633 0.3304 1.1741 0.056 Uiso 1 1 calc R U . . .
C117 C 0.4970(11) 0.4286(10) 1.0690(8) 0.038(2) Uani 1 1 d . . . . .
H11C H 0.4529 0.4767 1.1060 0.045 Uiso 1 1 calc R U . . .
C118 C 0.7041(9) 0.2356(8) 0.8993(7) 0.0297(18) Uani 1 1 d . . . . .
H11F H 0.8099 0.2872 0.9309 0.036 Uiso 1 1 calc R U . . .
H11G H 0.6995 0.1498 0.9050 0.036 Uiso 1 1 calc R U . . .
C120 C 0.2010(9) 0.2217(7) 0.6408(7) 0.0261(17) Uani 1 1 d . . . . .
S121 S 0.0195(2) 0.1599(2) 0.58527(19) 0.0333(5) Uani 1 1 d . . . . .
C123 C 0.9113(8) 0.5334(7) 0.9119(6) 0.0200(16) Uani 1 1 d . . . . .
S124 S 1.0835(2) 0.5380(2) 0.97998(16) 0.0267(4) Uani 1 1 d . . . . .
C202 C 0.3843(9) -0.1696(8) 0.1897(7) 0.0277(18) Uani 1 1 d . . . . .
H20A H 0.4816 -0.1038 0.2365 0.033 Uiso 1 1 calc R U . . .
H20B H 0.4019 -0.2515 0.1648 0.033 Uiso 1 1 calc R U . . .
C203 C 0.2897(10) -0.1824(9) 0.2521(8) 0.036(2) Uani 1 1 d . . . . .
H20C H 0.1940 -0.2507 0.2066 0.043 Uiso 1 1 calc R U . . .
H20D H 0.3419 -0.2035 0.3169 0.043 Uiso 1 1 calc R U . . .
C205 C 0.1668(11) -0.0608(10) 0.3342(7) 0.040(2) Uani 1 1 d . . . . .
H20E H 0.2089 -0.0795 0.4021 0.048 Uiso 1 1 calc R U . . .
H20F H 0.0693 -0.1261 0.2869 0.048 Uiso 1 1 calc R U . . .
C206 C 0.1484(11) 0.0711(10) 0.3576(7) 0.040(2) Uani 1 1 d . . . . .
H20G H 0.0742 0.0744 0.3878 0.048 Uiso 1 1 calc R U . . .
H20H H 0.2440 0.1363 0.4097 0.048 Uiso 1 1 calc R U . . .
C208 C 0.0778(11) 0.2132(10) 0.2583(9) 0.040(2) Uani 1 1 d . . . . .
H20I H 0.1710 0.2823 0.3087 0.048 Uiso 1 1 calc R U . . .
H20J H -0.0002 0.2232 0.2834 0.048 Uiso 1 1 calc R U . . .
C209 C 0.0336(10) 0.2222(9) 0.1499(8) 0.034(2) Uani 1 1 d . . . . .
H20K H 0.0238 0.3074 0.1512 0.041 Uiso 1 1 calc R U . . .
H20L H -0.0636 0.1575 0.1005 0.041 Uiso 1 1 calc R U . . .
C211 C 0.1021(10) 0.1869(9) -0.0035(7) 0.0326(19) Uani 1 1 d . . . . .
H21D H 0.1166 0.2720 -0.0121 0.039 Uiso 1 1 calc R U . . .
H21E H -0.0045 0.1375 -0.0450 0.039 Uiso 1 1 calc R U . . .
C212 C 0.1925(9) 0.1204(7) -0.0454(7) 0.0225(16) Uani 1 1 d . . . . .
C214 C 0.3324(8) -0.0221(7) -0.0272(7) 0.0227(16) Uani 1 1 d . . . . .
C215 C 0.3499(9) -0.0197(8) -0.1225(7) 0.0259(17) Uani 1 1 d . . . . .
H21A H 0.4026 -0.0694 -0.1485 0.031 Uiso 1 1 calc R U . . .
C216 C 0.2875(10) 0.0574(8) -0.1768(7) 0.0299(18) Uani 1 1 d . . . . .
H21B H 0.2980 0.0611 -0.2406 0.036 Uiso 1 1 calc R U . . .
C217 C 0.2111(10) 0.1278(8) -0.1387(6) 0.0278(17) Uani 1 1 d . . . . .
H21C H 0.1705 0.1817 -0.1752 0.033 Uiso 1 1 calc R U . . .
C218 C 0.3957(9) -0.0978(8) 0.0400(7) 0.0248(16) Uani 1 1 d . . . . .
H21F H 0.3997 -0.1758 -0.0064 0.030 Uiso 1 1 calc R U . . .
H21G H 0.4984 -0.0473 0.0931 0.030 Uiso 1 1 calc R U . . .
C220 C -0.1295(9) -0.1076(7) -0.0044(7) 0.0241(17) Uani 1 1 d . . . . .
S221 S -0.3012(2) -0.1079(2) -0.0572(2) 0.0428(6) Uani 1 1 d . . . . .
C223 C 0.5610(9) 0.1700(7) 0.2854(6) 0.0252(18) Uani 1 1 d . . . . .
S224 S 0.7358(2) 0.1793(2) 0.3309(2) 0.0402(6) Uani 1 1 d . . . . .
C302 C 0.7331(10) 0.8731(8) 0.5379(8) 0.0309(19) Uani 1 1 d . . . . .
H30A H 0.6351 0.8066 0.5039 0.037 Uiso 1 1 calc R U . . .
H30B H 0.7167 0.9568 0.5413 0.037 Uiso 1 1 calc R U . . .
C303 C 0.8209(11) 0.8726(8) 0.6506(8) 0.035(2) Uani 1 1 d . . . . .
H30C H 0.9177 0.9407 0.6860 0.042 Uiso 1 1 calc R U . . .
H30D H 0.7651 0.8861 0.6952 0.042 Uiso 1 1 calc R U . . .
C305 C 0.9404(11) 0.7380(10) 0.7354(7) 0.039(2) Uani 1 1 d . . . . .
H30E H 0.9002 0.7520 0.7902 0.047 Uiso 1 1 calc R U . . .
H30F H 1.0397 0.8015 0.7646 0.047 Uiso 1 1 calc R U . . .
C306 C 0.9508(10) 0.6062(9) 0.7074(7) 0.032(2) Uani 1 1 d . . . . .
H30G H 1.0250 0.5952 0.7703 0.039 Uiso 1 1 calc R U . . .
H30H H 0.8535 0.5431 0.6855 0.039 Uiso 1 1 calc R U . . .
C308 C 0.9918(10) 0.4606(8) 0.5783(7) 0.0300(19) Uani 1 1 d . . . . .
H30I H 0.8895 0.4012 0.5465 0.036 Uiso 1 1 calc R U . . .
H30J H 1.0560 0.4342 0.6356 0.036 Uiso 1 1 calc R U . . .
C309 C 1.0487(10) 0.4595(9) 0.4934(8) 0.0321(19) Uani 1 1 d . . . . .
H30K H 1.1522 0.5168 0.5261 0.039 Uiso 1 1 calc R U . . .
H30L H 1.0475 0.3724 0.4596 0.039 Uiso 1 1 calc R U . . .
C311 C 1.0075(10) 0.5352(9) 0.3339(8) 0.033(2) Uani 1 1 d . . . . .
H31D H 0.9995 0.4559 0.2818 0.039 Uiso 1 1 calc R U . . .
H31E H 1.1137 0.5866 0.3732 0.039 Uiso 1 1 calc R U . . .
C312 C 0.9216(10) 0.6086(8) 0.2744(7) 0.0258(17) Uani 1 1 d . . . . .
C314 C 0.7947(8) 0.7588(7) 0.2884(6) 0.0225(16) Uani 1 1 d . . . . .
C315 C 0.7719(11) 0.7598(9) 0.1855(7) 0.034(2) Uani 1 1 d . . . . .
H31A H 0.7230 0.8151 0.1567 0.041 Uiso 1 1 calc R U . . .
C316 C 0.8197(12) 0.6813(10) 0.1259(8) 0.042(2) Uani 1 1 d . . . . .
H31B H 0.8013 0.6801 0.0545 0.050 Uiso 1 1 calc R U . . .
C317 C 0.8953(10) 0.6027(9) 0.1684(7) 0.035(2) Uani 1 1 d . . . . .
H31C H 0.9280 0.5468 0.1270 0.042 Uiso 1 1 calc R U . . .
C318 C 0.7363(9) 0.8319(8) 0.3592(7) 0.0251(16) Uani 1 1 d . . . . .
H31F H 0.7436 0.9169 0.3508 0.030 Uiso 1 1 calc R U . . .
H31G H 0.6301 0.7864 0.3357 0.030 Uiso 1 1 calc R U . . .
C320 C 0.5368(9) 0.5366(7) 0.3529(6) 0.0205(16) Uani 1 1 d . . . . .
S321 S 0.3610(2) 0.5193(2) 0.27865(17) 0.0255(4) Uani 1 1 d . . . . .
C323 C 1.2530(9) 0.8484(7) 0.5868(7) 0.0253(17) Uani 1 1 d . . . . .
S324 S 1.4288(2) 0.9119(2) 0.6200(2) 0.0404(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1A N1A 2.196(6) . ?
Mn1A N5A 2.210(7) . ?
Mn1A N4A 2.238(7) . ?
Mn1A O1A 2.294(6) . ?
Mn1A N2A 2.308(7) . ?
Mn1A O2A 2.310(6) . ?
Mn1A N3A 2.334(7) . ?
Mn1C N4C 2.199(7) . ?
Mn1C N5C 2.233(7) . ?
Mn1C N1C 2.233(6) . ?
Mn1C O1C 2.276(6) . ?
Mn1C N3C 2.282(7) . ?
Mn1C O2C 2.306(5) . ?
Mn1C N2C 2.309(7) . ?
Mn1B N4B 2.194(7) . ?
Mn1B N5B 2.201(8) . ?
Mn1B N1B 2.210(6) . ?
Mn1B N2B 2.297(7) . ?
Mn1B O1B 2.301(6) . ?
Mn1B N3B 2.303(7) . ?
Mn1B O2B 2.314(5) . ?
N1A C114 1.333(11) . ?
N1A C112 1.334(11) . ?
N1C C312 1.333(11) . ?
N1C C314 1.358(10) . ?
N1B C214 1.336(11) . ?
N1B C212 1.354(10) . ?
O1A C108 1.425(12) . ?
O1A C106 1.443(12) . ?
O1C C306 1.408(11) . ?
O1C C308 1.435(10) . ?
O1B C205 1.428(11) . ?
O1B C203 1.429(12) . ?
N2A C109 1.460(10) . ?
N2A C111 1.468(10) . ?
N2A H2AA 1.0000 . ?
N2C C311 1.468(10) . ?
N2C C309 1.495(10) . ?
N2C H2CA 1.0000 . ?
N2B C202 1.463(10) . ?
N2B C218 1.478(10) . ?
N2B H2BA 1.0000 . ?
O2A C103 1.418(12) . ?
O2A C105 1.453(11) . ?
O2C C303 1.434(11) . ?
O2C C305 1.442(11) . ?
O2B C206 1.422(12) . ?
O2B C208 1.428(12) . ?
N3A C118 1.466(11) . ?
N3A C102 1.474(10) . ?
N3A H3AA 1.0000 . ?
N3C C302 1.480(11) . ?
N3C C318 1.483(10) . ?
N3C H3CA 1.0000 . ?
N3B C209 1.469(10) . ?
N3B C211 1.486(11) . ?
N3B H3BA 1.0000 . ?
N4A C123 1.153(11) . ?
N4C C323 1.174(11) . ?
N4B C223 1.140(12) . ?
N5A C120 1.139(11) . ?
N5C C320 1.167(11) . ?
N5B C220 1.160(11) . ?
C102 C103 1.500(15) . ?
C102 H10A 0.9900 . ?
C102 H10B 0.9900 . ?
C103 H10C 0.9900 . ?
C103 H10D 0.9900 . ?
C105 C106 1.488(16) . ?
C105 H10E 0.9900 . ?
C105 H10F 0.9900 . ?
C106 H10G 0.9900 . ?
C106 H10H 0.9900 . ?
C108 C109 1.513(13) . ?
C108 H10I 0.9900 . ?
C108 H10J 0.9900 . ?
C109 H10K 0.9900 . ?
C109 H10L 0.9900 . ?
C111 C112 1.507(12) . ?
C111 H11D 0.9900 . ?
C111 H11E 0.9900 . ?
C112 C117 1.381(13) . ?
C114 C115 1.391(12) . ?
C114 C118 1.508(12) . ?
C115 C116 1.383(15) . ?
C115 H11A 0.9500 . ?
C116 C117 1.411(15) . ?
C116 H11B 0.9500 . ?
C117 H11C 0.9500 . ?
C118 H11F 0.9900 . ?
C118 H11G 0.9900 . ?
C120 S121 1.641(8) . ?
C123 S124 1.649(8) . ?
C202 C203 1.521(12) . ?
C202 H20A 0.9900 . ?
C202 H20B 0.9900 . ?
C203 H20C 0.9900 . ?
C203 H20D 0.9900 . ?
C205 C206 1.522(16) . ?
C205 H20E 0.9900 . ?
C205 H20F 0.9900 . ?
C206 H20G 0.9900 . ?
C206 H20H 0.9900 . ?
C208 C209 1.464(15) . ?
C208 H20I 0.9900 . ?
C208 H20J 0.9900 . ?
C209 H20K 0.9900 . ?
C209 H20L 0.9900 . ?
C211 C212 1.489(12) . ?
C211 H21D 0.9900 . ?
C211 H21E 0.9900 . ?
C212 C217 1.410(12) . ?
C214 C215 1.421(12) . ?
C214 C218 1.487(11) . ?
C215 C216 1.392(12) . ?
C215 H21A 0.9500 . ?
C216 C217 1.369(12) . ?
C216 H21B 0.9500 . ?
C217 H21C 0.9500 . ?
C218 H21F 0.9900 . ?
C218 H21G 0.9900 . ?
C220 S221 1.630(8) . ?
C223 S224 1.627(8) . ?
C302 C303 1.520(14) . ?
C302 H30A 0.9900 . ?
C302 H30B 0.9900 . ?
C303 H30C 0.9900 . ?
C303 H30D 0.9900 . ?
C305 C306 1.493(15) . ?
C305 H30E 0.9900 . ?
C305 H30F 0.9900 . ?
C306 H30G 0.9900 . ?
C306 H30H 0.9900 . ?
C308 C309 1.499(13) . ?
C308 H30I 0.9900 . ?
C308 H30J 0.9900 . ?
C309 H30K 0.9900 . ?
C309 H30L 0.9900 . ?
C311 C312 1.500(13) . ?
C311 H31D 0.9900 . ?
C311 H31E 0.9900 . ?
C312 C317 1.402(12) . ?
C314 C315 1.387(11) . ?
C314 C318 1.506(11) . ?
C315 C316 1.361(14) . ?
C315 H31A 0.9500 . ?
C316 C317 1.392(15) . ?
C316 H31B 0.9500 . ?
C317 H31C 0.9500 . ?
C318 H31F 0.9900 . ?
C318 H31G 0.9900 . ?
C320 S321 1.658(8) . ?
C323 S324 1.628(8) . ?

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
N1A Mn1A N5A 91.7(3) . . ?
N1A Mn1A N4A 88.0(2) . . ?
N5A Mn1A N4A 176.7(3) . . ?
N1A Mn1A O1A 143.6(3) . . ?
N5A Mn1A O1A 81.6(3) . . ?
N4A Mn1A O1A 100.6(2) . . ?
N1A Mn1A N2A 72.8(2) . . ?
N5A Mn1A N2A 94.8(3) . . ?
N4A Mn1A N2A 88.3(2) . . ?
O1A Mn1A N2A 72.2(2) . . ?
N1A Mn1A O2A 145.1(3) . . ?
N5A Mn1A O2A 94.6(3) . . ?
N4A Mn1A O2A 83.7(2) . . ?
O1A Mn1A O2A 71.3(2) . . ?
N2A Mn1A O2A 140.4(2) . . ?
N1A Mn1A N3A 72.3(2) . . ?
N5A Mn1A N3A 87.3(3) . . ?
N4A Mn1A N3A 89.5(3) . . ?
O1A Mn1A N3A 142.2(2) . . ?
N2A Mn1A N3A 145.1(2) . . ?
O2A Mn1A N3A 73.8(2) . . ?
N4C Mn1C N5C 174.9(3) . . ?
N4C Mn1C N1C 89.8(3) . . ?
N5C Mn1C N1C 85.2(2) . . ?
N4C Mn1C O1C 82.7(3) . . ?
N5C Mn1C O1C 101.9(2) . . ?
N1C Mn1C O1C 144.7(2) . . ?
N4C Mn1C N3C 88.1(3) . . ?
N5C Mn1C N3C 89.6(2) . . ?
N1C Mn1C N3C 73.1(2) . . ?
O1C Mn1C N3C 140.5(2) . . ?
N4C Mn1C O2C 97.2(3) . . ?
N5C Mn1C O2C 86.4(2) . . ?
N1C Mn1C O2C 145.1(3) . . ?
O1C Mn1C O2C 70.2(2) . . ?
N3C Mn1C O2C 73.1(2) . . ?
N4C Mn1C N2C 93.7(3) . . ?
N5C Mn1C N2C 85.7(2) . . ?
N1C Mn1C N2C 72.5(2) . . ?
O1C Mn1C N2C 73.6(2) . . ?
N3C Mn1C N2C 145.5(2) . . ?
O2C Mn1C N2C 140.4(2) . . ?
N4B Mn1B N5B 179.2(3) . . ?
N4B Mn1B N1B 90.8(3) . . ?
N5B Mn1B N1B 88.6(3) . . ?
N4B Mn1B N2B 93.8(3) . . ?
N5B Mn1B N2B 86.6(3) . . ?
N1B Mn1B N2B 72.8(2) . . ?
N4B Mn1B O1B 83.0(2) . . ?
N5B Mn1B O1B 97.9(3) . . ?
N1B Mn1B O1B 145.0(3) . . ?
N2B Mn1B O1B 73.2(2) . . ?
N4B Mn1B N3B 87.5(3) . . ?
N5B Mn1B N3B 91.7(3) . . ?
N1B Mn1B N3B 72.9(3) . . ?
N2B Mn1B N3B 145.7(2) . . ?
O1B Mn1B N3B 140.6(3) . . ?
N4B Mn1B O2B 96.8(3) . . ?
N5B Mn1B O2B 83.3(3) . . ?
N1B Mn1B O2B 144.6(2) . . ?
N2B Mn1B O2B 140.4(2) . . ?
O1B Mn1B O2B 70.5(2) . . ?
N3B Mn1B O2B 72.9(2) . . ?
C114 N1A C112 119.9(7) . . ?
C114 N1A Mn1A 121.2(5) . . ?
C112 N1A Mn1A 118.9(6) . . ?
C312 N1C C314 121.4(7) . . ?
C312 N1C Mn1C 119.3(5) . . ?
C314 N1C Mn1C 119.1(5) . . ?
C214 N1B C212 122.3(7) . . ?
C214 N1B Mn1B 119.3(5) . . ?
C212 N1B Mn1B 118.4(5) . . ?
C108 O1A C106 114.5(7) . . ?
C108 O1A Mn1A 114.8(5) . . ?
C106 O1A Mn1A 116.0(6) . . ?
C306 O1C C308 113.3(6) . . ?
C306 O1C Mn1C 117.5(5) . . ?
C308 O1C Mn1C 113.4(4) . . ?
C205 O1B C203 114.5(7) . . ?
C205 O1B Mn1B 114.4(5) . . ?
C203 O1B Mn1B 113.8(5) . . ?
C109 N2A C111 113.8(7) . . ?
C109 N2A Mn1A 111.8(6) . . ?
C111 N2A Mn1A 110.5(5) . . ?
C109 N2A H2AA 106.8 . . ?
C111 N2A H2AA 106.8 . . ?
Mn1A N2A H2AA 106.8 . . ?
C311 N2C C309 116.1(7) . . ?
C311 N2C Mn1C 109.0(5) . . ?
C309 N2C Mn1C 110.1(5) . . ?
C311 N2C H2CA 107.1 . . ?
C309 N2C H2CA 107.1 . . ?
Mn1C N2C H2CA 107.1 . . ?
C202 N2B C218 113.4(6) . . ?
C202 N2B Mn1B 110.5(5) . . ?
C218 N2B Mn1B 109.8(5) . . ?
C202 N2B H2BA 107.6 . . ?
C218 N2B H2BA 107.6 . . ?
Mn1B N2B H2BA 107.6 . . ?
C103 O2A C105 113.9(7) . . ?
C103 O2A Mn1A 113.4(5) . . ?
C105 O2A Mn1A 112.1(6) . . ?
C303 O2C C305 113.5(7) . . ?
C303 O2C Mn1C 114.4(5) . . ?
C305 O2C Mn1C 113.2(5) . . ?
C206 O2B C208 116.4(7) . . ?
C206 O2B Mn1B 115.9(6) . . ?
C208 O2B Mn1B 112.6(5) . . ?
C118 N3A C102 117.3(7) . . ?
C118 N3A Mn1A 109.9(5) . . ?
C102 N3A Mn1A 106.9(5) . . ?
C118 N3A H3AA 107.5 . . ?
C102 N3A H3AA 107.5 . . ?
Mn1A N3A H3AA 107.5 . . ?
C302 N3C C318 112.5(7) . . ?
C302 N3C Mn1C 110.4(5) . . ?
C318 N3C Mn1C 111.2(5) . . ?
C302 N3C H3CA 107.5 . . ?
C318 N3C H3CA 107.5 . . ?
Mn1C N3C H3CA 107.5 . . ?
C209 N3B C211 113.1(7) . . ?
C209 N3B Mn1B 110.8(6) . . ?
C211 N3B Mn1B 111.3(5) . . ?
C209 N3B H3BA 107.1 . . ?
C211 N3B H3BA 107.1 . . ?
Mn1B N3B H3BA 107.1 . . ?
C123 N4A Mn1A 145.7(6) . . ?
C323 N4C Mn1C 165.2(7) . . ?
C223 N4B Mn1B 141.1(7) . . ?
C120 N5A Mn1A 165.0(8) . . ?
C320 N5C Mn1C 149.2(6) . . ?
C220 N5B Mn1B 142.9(7) . . ?
N3A C102 C103 110.6(8) . . ?
N3A C102 H10A 109.5 . . ?
C103 C102 H10A 109.5 . . ?
N3A C102 H10B 109.5 . . ?
C103 C102 H10B 109.5 . . ?
H10A C102 H10B 108.1 . . ?
O2A C103 C102 106.1(7) . . ?
O2A C103 H10C 110.5 . . ?
C102 C103 H10C 110.5 . . ?
O2A C103 H10D 110.5 . . ?
C102 C103 H10D 110.5 . . ?
H10C C103 H10D 108.7 . . ?
O2A C105 C106 108.0(7) . . ?
O2A C105 H10E 110.1 . . ?
C106 C105 H10E 110.1 . . ?
O2A C105 H10F 110.1 . . ?
C106 C105 H10F 110.1 . . ?
H10E C105 H10F 108.4 . . ?
O1A C106 C105 107.2(7) . . ?
O1A C106 H10G 110.3 . . ?
C105 C106 H10G 110.3 . . ?
O1A C106 H10H 110.3 . . ?
C105 C106 H10H 110.3 . . ?
H10G C106 H10H 108.5 . . ?
O1A C108 C109 105.9(7) . . ?
O1A C108 H10I 110.6 . . ?
C109 C108 H10I 110.6 . . ?
O1A C108 H10J 110.6 . . ?
C109 C108 H10J 110.6 . . ?
H10I C108 H10J 108.7 . . ?
N2A C109 C108 108.9(7) . . ?
N2A C109 H10K 109.9 . . ?
C108 C109 H10K 109.9 . . ?
N2A C109 H10L 109.9 . . ?
C108 C109 H10L 109.9 . . ?
H10K C109 H10L 108.3 . . ?
N2A C111 C112 109.4(7) . . ?
N2A C111 H11D 109.8 . . ?
C112 C111 H11D 109.8 . . ?
N2A C111 H11E 109.8 . . ?
C112 C111 H11E 109.8 . . ?
H11D C111 H11E 108.2 . . ?
N1A C112 C117 122.0(8) . . ?
N1A C112 C111 117.2(7) . . ?
C117 C112 C111 120.8(8) . . ?
N1A C114 C115 122.7(8) . . ?
N1A C114 C118 114.9(6) . . ?
C115 C114 C118 122.2(8) . . ?
C116 C115 C114 117.5(9) . . ?
C116 C115 H11A 121.3 . . ?
C114 C115 H11A 121.3 . . ?
C115 C116 C117 119.9(8) . . ?
C115 C116 H11B 120.0 . . ?
C117 C116 H11B 120.0 . . ?
C112 C117 C116 118.0(9) . . ?
C112 C117 H11C 121.0 . . ?
C116 C117 H11C 121.0 . . ?
N3A C118 C114 111.1(7) . . ?
N3A C118 H11F 109.4 . . ?
C114 C118 H11F 109.4 . . ?
N3A C118 H11G 109.4 . . ?
C114 C118 H11G 109.4 . . ?
H11F C118 H11G 108.0 . . ?
N5A C120 S121 177.8(8) . . ?
N4A C123 S124 178.1(7) . . ?
N2B C202 C203 108.2(7) . . ?
N2B C202 H20A 110.0 . . ?
C203 C202 H20A 110.0 . . ?
N2B C202 H20B 110.0 . . ?
C203 C202 H20B 110.0 . . ?
H20A C202 H20B 108.4 . . ?
O1B C203 C202 107.0(7) . . ?
O1B C203 H20C 110.3 . . ?
C202 C203 H20C 110.3 . . ?
O1B C203 H20D 110.3 . . ?
C202 C203 H20D 110.3 . . ?
H20C C203 H20D 108.6 . . ?
O1B C205 C206 107.9(7) . . ?
O1B C205 H20E 110.1 . . ?
C206 C205 H20E 110.1 . . ?
O1B C205 H20F 110.1 . . ?
C206 C205 H20F 110.1 . . ?
H20E C205 H20F 108.4 . . ?
O2B C206 C205 105.6(7) . . ?
O2B C206 H20G 110.6 . . ?
C205 C206 H20G 110.6 . . ?
O2B C206 H20H 110.6 . . ?
C205 C206 H20H 110.6 . . ?
H20G C206 H20H 108.7 . . ?
O2B C208 C209 109.6(8) . . ?
O2B C208 H20I 109.7 . . ?
C209 C208 H20I 109.7 . . ?
O2B C208 H20J 109.7 . . ?
C209 C208 H20J 109.7 . . ?
H20I C208 H20J 108.2 . . ?
C208 C209 N3B 108.8(8) . . ?
C208 C209 H20K 109.9 . . ?
N3B C209 H20K 109.9 . . ?
C208 C209 H20L 109.9 . . ?
N3B C209 H20L 109.9 . . ?
H20K C209 H20L 108.3 . . ?
N3B C211 C212 109.8(7) . . ?
N3B C211 H21D 109.7 . . ?
C212 C211 H21D 109.7 . . ?
N3B C211 H21E 109.7 . . ?
C212 C211 H21E 109.7 . . ?
H21D C211 H21E 108.2 . . ?
N1B C212 C217 119.0(7) . . ?
N1B C212 C211 117.8(7) . . ?
C217 C212 C211 123.2(7) . . ?
N1B C214 C215 120.3(7) . . ?
N1B C214 C218 115.8(7) . . ?
C215 C214 C218 123.9(7) . . ?
C216 C215 C214 118.1(7) . . ?
C216 C215 H21A 120.9 . . ?
C214 C215 H21A 120.9 . . ?
C217 C216 C215 120.3(8) . . ?
C217 C216 H21B 119.9 . . ?
C215 C216 H21B 119.9 . . ?
C216 C217 C212 120.0(7) . . ?
C216 C217 H21C 120.0 . . ?
C212 C217 H21C 120.0 . . ?
N2B C218 C214 111.0(6) . . ?
N2B C218 H21F 109.4 . . ?
C214 C218 H21F 109.4 . . ?
N2B C218 H21G 109.4 . . ?
C214 C218 H21G 109.4 . . ?
H21F C218 H21G 108.0 . . ?
N5B C220 S221 175.6(8) . . ?
N4B C223 S224 177.6(8) . . ?
N3C C302 C303 108.0(7) . . ?
N3C C302 H30A 110.1 . . ?
C303 C302 H30A 110.1 . . ?
N3C C302 H30B 110.1 . . ?
C303 C302 H30B 110.1 . . ?
H30A C302 H30B 108.4 . . ?
O2C C303 C302 106.0(7) . . ?
O2C C303 H30C 110.5 . . ?
C302 C303 H30C 110.5 . . ?
O2C C303 H30D 110.5 . . ?
C302 C303 H30D 110.5 . . ?
H30C C303 H30D 108.7 . . ?
O2C C305 C306 106.6(7) . . ?
O2C C305 H30E 110.4 . . ?
C306 C305 H30E 110.4 . . ?
O2C C305 H30F 110.4 . . ?
C306 C305 H30F 110.4 . . ?
H30E C305 H30F 108.6 . . ?
O1C C306 C305 107.4(7) . . ?
O1C C306 H30G 110.2 . . ?
C305 C306 H30G 110.2 . . ?
O1C C306 H30H 110.2 . . ?
C305 C306 H30H 110.2 . . ?
H30G C306 H30H 108.5 . . ?
O1C C308 C309 106.7(6) . . ?
O1C C308 H30I 110.4 . . ?
C309 C308 H30I 110.4 . . ?
O1C C308 H30J 110.4 . . ?
C309 C308 H30J 110.4 . . ?
H30I C308 H30J 108.6 . . ?
N2C C309 C308 108.5(7) . . ?
N2C C309 H30K 110.0 . . ?
C308 C309 H30K 110.0 . . ?
N2C C309 H30L 110.0 . . ?
C308 C309 H30L 110.0 . . ?
H30K C309 H30L 108.4 . . ?
N2C C311 C312 110.9(6) . . ?
N2C C311 H31D 109.5 . . ?
C312 C311 H31D 109.5 . . ?
N2C C311 H31E 109.5 . . ?
C312 C311 H31E 109.5 . . ?
H31D C311 H31E 108.0 . . ?
N1C C312 C317 120.8(8) . . ?
N1C C312 C311 114.7(7) . . ?
C317 C312 C311 124.5(8) . . ?
N1C C314 C315 119.6(8) . . ?
N1C C314 C318 115.1(7) . . ?
C315 C314 C318 125.2(7) . . ?
C316 C315 C314 119.7(8) . . ?
C316 C315 H31A 120.1 . . ?
C314 C315 H31A 120.1 . . ?
C315 C316 C317 120.6(8) . . ?
C315 C316 H31B 119.7 . . ?
C317 C316 H31B 119.7 . . ?
C316 C317 C312 117.8(9) . . ?
C316 C317 H31C 121.1 . . ?
C312 C317 H31C 121.1 . . ?
N3C C318 C314 112.0(7) . . ?
N3C C318 H31F 109.2 . . ?
C314 C318 H31F 109.2 . . ?
N3C C318 H31G 109.2 . . ?
C314 C318 H31G 109.2 . . ?
H31F C318 H31G 107.9 . . ?
N5C C320 S321 178.1(7) . . ?
N4C C323 S324 179.2(8) . . ?

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
N2A H2AA S221 1.00 2.76 3.586(7) 140.4 1_666
N2C H2CA S224 1.00 2.74 3.565(7) 140.5 .
N2B H2BA S124 1.00 2.70 3.583(7) 147.8 1_444
N3A H3AA S324 1.00 2.62 3.488(7) 145.5 1_445
N3C H3CA S121 1.00 2.50 3.378(7) 147.1 1_665
N3B H3BA S321 1.00 2.65 3.550(7) 150.2 .
C106 H10G O2C 0.99 2.59 3.561(11) 167.6 .
C106 H10H S321 0.99 3.01 3.898(9) 149.9 .
C108 H10I S324 0.99 2.98 3.681(9) 128.8 1_455
C108 H10J S221 0.99 2.95 3.667(9) 129.9 1_666
C117 H11C S321 0.95 2.87 3.706(9) 146.9 1_556
C206 H20G S121 0.99 3.01 3.874(10) 146.9 .
C208 H20J S224 0.99 2.96 3.922(9) 164.8 1_455
C215 H21A S221 0.95 2.98 3.728(9) 136.2 1_655
C306 H30H O2A 0.99 2.62 3.596(10) 168.6 .
C308 H30J S121 0.99 2.94 3.502(8) 116.6 1_655
C317 H31C S124 0.95 3.01 3.806(9) 142.0 1_554

_refine_diff_density_max         4.061
_refine_diff_density_min         -1.033
_refine_diff_density_rms         0.147

