# 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 2015

####################################################################### 
# 
# 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_c:\cz416\cz416
_database_code_depnum_ccdc_archive 'CCDC 967021'
_audit_update_record             
;
2015-03-13 deposited with the CCDC.
2015-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_common            
(iron(II)-benzenedisulfonate)(N-methylpyrrolidone)
_chemical_formula_moiety         'C21 H31 Fe N3 O9 S2'
_chemical_formula_sum            'C21 H31 Fe N3 O9 S2'
_chemical_formula_weight         589.46


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'
Fe Fe 0.3463 0.8444 '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      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                   9.1198(5)
_cell_length_b                   9.6075(5)
_cell_length_c                   14.3241(8)
_cell_angle_alpha                94.951(2)
_cell_angle_beta                 98.050(3)
_cell_angle_gamma                92.029(2)
_cell_volume                     1236.62(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9878
_cell_measurement_theta_min      3.70
_cell_measurement_theta_max      40.26

_exptl_crystal_description       blocks
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.248
_exptl_crystal_size_min          0.152
_exptl_absorpt_coefficient_mu    0.836
_shelx_estimated_absorpt_T_min   0.794
_shelx_estimated_absorpt_T_max   0.884
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7937
_exptl_absorpt_correction_T_max  0.8835
_exptl_absorpt_process_details   'Bruker SAINT'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            90529
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.885
_diffrn_reflns_theta_max         37.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             13013
_reflns_number_gt                11455
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0394P)²+0.1595P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         13013
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0238
_refine_ls_wR_factor_ref         0.0705
_refine_ls_wR_factor_gt          0.0689
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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
Fe1 Fe 0.98961(2) 0.51642(2) 0.17686(2) 0.00851(2) Uani 1 1 d . . . . .
S1 S 0.20734(2) 0.65387(2) 0.03062(2) 0.00843(3) Uani 1 1 d . . . . .
O11 O 0.90821(5) 0.39076(5) 0.04813(3) 0.01232(8) Uani 1 1 d . . . . .
O13 O 0.24975(6) 0.80134(5) 0.03392(4) 0.01609(9) Uani 1 1 d . . . . .
O12 O 0.17018(6) 0.61332(6) 0.12102(4) 0.01385(8) Uani 1 1 d . . . . .
C1 C 0.37011(7) 0.56436(6) 0.01321(4) 0.00938(9) Uani 1 1 d . . . . .
C2 C 0.43728(7) 0.58739(7) 0.93388(5) 0.01242(10) Uani 1 1 d . . . . .
H2 H 0.3942 0.6471 0.8892 0.015 Uiso 1 1 calc R U . . .
C3 C 0.43219(7) 0.47757(7) 0.07952(5) 0.01242(10) Uani 1 1 d . . . . .
H3 H 0.3859 0.4628 0.1335 0.015 Uiso 1 1 calc R U . . .
S2 S 0.76549(2) 0.37521(2) 0.32711(2) 0.01220(3) Uani 1 1 d . . . . .
O14 O 0.82174(6) 0.42139(6) 0.24324(4) 0.01576(9) Uani 1 1 d . . . . .
O15 O 0.76513(8) 0.22428(6) 0.32788(4) 0.02261(11) Uani 1 1 d . . . . .
O16 O 0.62617(6) 0.43579(7) 0.34084(4) 0.02116(11) Uani 1 1 d . . . . .
C4 C 0.89630(7) 0.44434(7) 0.42498(5) 0.01233(10) Uani 1 1 d . . . . .
C5 C 0.85967(8) 0.55423(7) 0.48573(5) 0.01487(11) Uani 1 1 d . . . . .
H5 H 0.7639 0.5909 0.4758 0.018 Uiso 1 1 calc R U . . .
C6 C 0.03612(8) 0.38978(7) 0.43881(5) 0.01522(11) Uani 1 1 d . . . . .
H6 H 0.0604 0.3147 0.3970 0.018 Uiso 1 1 calc R U . . .
O1 O 0.05974(6) 0.65623(5) 0.30327(4) 0.01353(8) Uani 1 1 d . . . . .
C11 C 0.18342(7) 0.68833(6) 0.35026(5) 0.01139(9) Uani 1 1 d . . . . .
C12 C 0.32811(8) 0.62323(8) 0.33892(6) 0.01946(13) Uani 1 1 d . . . . .
H12A H 0.3643 0.6495 0.2805 0.023 Uiso 1 1 calc R U . . .
H12B H 0.3172 0.5200 0.3361 0.023 Uiso 1 1 calc R U . . .
C13 C 0.43430(8) 0.68205(8) 0.42691(6) 0.01889(12) Uani 1 1 d . . . . .
H13A H 0.5341 0.7038 0.4107 0.023 Uiso 1 1 calc R U . . .
H13B H 0.4430 0.6147 0.4757 0.023 Uiso 1 1 calc R U . . .
C14 C 0.36335(8) 0.81555(8) 0.46188(5) 0.01666(11) Uani 1 1 d . . . . .
H14A H 0.3739 0.8270 0.5319 0.020 Uiso 1 1 calc R U . . .
H14B H 0.4084 0.8993 0.4393 0.020 Uiso 1 1 calc R U . . .
N1 N 0.20818(7) 0.79203(6) 0.42024(4) 0.01339(9) Uani 1 1 d . . . . .
C15 C 0.09726(9) 0.88339(8) 0.44871(6) 0.01968(13) Uani 1 1 d . . . . .
H15A H 0.1009 0.8881 0.5176 0.024 Uiso 1 1 calc R U . . .
H15B H -0.0011 0.8470 0.4180 0.024 Uiso 1 1 calc R U . . .
H15C H 0.1166 0.9772 0.4299 0.024 Uiso 1 1 calc R U . . .
O2 O 0.85323(6) 0.66609(5) 0.12351(4) 0.01372(8) Uani 1 1 d . . . . .
C21 C 0.76032(7) 0.74537(6) 0.15104(5) 0.01216(10) Uani 1 1 d . . . . .
C22 C 0.70106(9) 0.75014(8) 0.24399(6) 0.01792(12) Uani 1 1 d . . . . .
H22A H 0.7828 0.7517 0.2975 0.022 Uiso 1 1 calc R U . . .
H22B H 0.6328 0.6683 0.2459 0.022 Uiso 1 1 calc R U . . .
C23 C 0.61897(14) 0.88542(11) 0.24821(9) 0.0353(2) Uani 1 1 d . . . . .
H23A H 0.6789 0.9595 0.2907 0.042 Uiso 1 1 calc R U . . .
H23B H 0.5229 0.8706 0.2715 0.042 Uiso 1 1 calc R U . . .
C24 C 0.59465(9) 0.92601(8) 0.14559(7) 0.02329(15) Uani 1 1 d . . . . .
H24A H 0.4911 0.9032 0.1155 0.028 Uiso 1 1 calc R U . . .
H24B H 0.6176 1.0271 0.1435 0.028 Uiso 1 1 calc R U . . .
N2 N 0.69772(7) 0.84183(6) 0.09908(5) 0.01647(10) Uani 1 1 d . . . . .
C25 C 0.72564(10) 0.86127(8) 0.00383(6) 0.02290(15) Uani 1 1 d . . . . .
H25A H 0.7678 0.9561 0.0021 0.027 Uiso 1 1 calc R U . . .
H25B H 0.6323 0.8479 -0.0398 0.027 Uiso 1 1 calc R U . . .
H25C H 0.7957 0.7930 -0.0152 0.027 Uiso 1 1 calc R U . . .
O3 O 0.13309(6) 0.35931(5) 0.21561(4) 0.01440(9) Uani 1 1 d . . . . .
C31 C 0.12270(7) 0.22871(6) 0.20932(5) 0.01085(9) Uani 1 1 d . . . . .
C32 C 0.99286(8) 0.13385(7) 0.16311(6) 0.01597(11) Uani 1 1 d . . . . .
H32A H 0.9791 0.1361 0.0935 0.019 Uiso 1 1 calc R U . . .
H32B H 0.9005 0.1618 0.1870 0.019 Uiso 1 1 calc R U . . .
C33 C 0.03393(8) 0.98813(7) 0.19074(6) 0.01909(13) Uani 1 1 d . . . . .
H33A H -0.0192 0.9614 0.2427 0.023 Uiso 1 1 calc R U . . .
H33B H 0.0091 0.9172 0.1359 0.023 Uiso 1 1 calc R U . . .
C34 C 0.20148(8) 0.00103(7) 0.22303(5) 0.01572(11) Uani 1 1 d . . . . .
H34A H 0.2288 -0.0487 0.2802 0.019 Uiso 1 1 calc R U . . .
H34B H 0.2562 -0.0373 0.1723 0.019 Uiso 1 1 calc R U . . .
N3 N 0.23264(7) 0.15151(6) 0.24365(5) 0.01456(10) Uani 1 1 d . . . . .
C35 C 0.37887(9) 0.20837(8) 0.28473(8) 0.02636(18) Uani 1 1 d . . . . .
H35A H 0.3996 0.1863 0.3507 0.032 Uiso 1 1 calc R U . . .
H35B H 0.3829 0.3101 0.2826 0.032 Uiso 1 1 calc R U . . .
H35C H 0.4530 0.1672 0.2487 0.032 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
Fe1 O2 2.0613(5) . ?
Fe1 O3 2.0927(5) 1_655 ?
Fe1 O14 2.1307(5) . ?
Fe1 O11 2.1396(5) . ?
Fe1 O12 2.1465(5) 1_655 ?
Fe1 O1 2.1649(5) 1_655 ?
S1 O13 1.4505(5) . ?
S1 O11 1.4553(5) 2_665 ?
S1 O12 1.4642(5) . ?
S1 C1 1.7783(6) . ?
O11 S1 1.4553(5) 2_665 ?
O12 Fe1 2.1465(5) 1_455 ?
C1 C3 1.3919(9) . ?
C1 C2 1.3942(9) 1_554 ?
C2 C3 1.3926(9) 2_666 ?
C2 C1 1.3942(9) 1_556 ?
C2 H2 0.9500 . ?
C3 C2 1.3926(9) 2_666 ?
C3 H3 0.9500 . ?
S2 O16 1.4473(6) . ?
S2 O15 1.4510(6) . ?
S2 O14 1.4669(5) . ?
S2 C4 1.7732(7) . ?
C4 C5 1.3898(10) . ?
C4 C6 1.3908(10) 1_655 ?
C5 C6 1.3916(10) 2_666 ?
C5 H5 0.9500 . ?
C6 C4 1.3908(10) 1_455 ?
C6 C5 1.3916(10) 2_666 ?
C6 H6 0.9500 . ?
O1 C11 1.2440(8) . ?
O1 Fe1 2.1649(5) 1_455 ?
C11 N1 1.3404(8) . ?
C11 C12 1.5032(10) . ?
C12 C13 1.5305(11) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.5340(11) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N1 1.4585(9) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
N1 C15 1.4410(9) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O2 C21 1.2414(8) . ?
C21 N2 1.3327(9) . ?
C21 C22 1.5032(10) . ?
C22 C23 1.5236(12) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.5414(15) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 N2 1.4553(10) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
N2 C25 1.4488(11) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
O3 C31 1.2495(8) . ?
O3 Fe1 2.0927(5) 1_455 ?
C31 N3 1.3321(8) . ?
C31 C32 1.5068(9) 1_455 ?
C32 C31 1.5069(9) 1_655 ?
C32 C33 1.5324(10) 1_645 ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.5307(10) 1_565 ?
C33 C32 1.5324(10) 1_465 ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 N3 1.4601(9) . ?
C34 C33 1.5307(10) 1_545 ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
N3 C35 1.4479(10) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Fe1 O3 173.60(2) . 1_655 ?
O2 Fe1 O14 93.58(2) . . ?
O3 Fe1 O14 90.32(2) 1_655 . ?
O2 Fe1 O11 85.71(2) . . ?
O3 Fe1 O11 89.27(2) 1_655 . ?
O14 Fe1 O11 89.33(2) . . ?
O2 Fe1 O12 89.26(2) . 1_655 ?
O3 Fe1 O12 87.19(2) 1_655 1_655 ?
O14 Fe1 O12 175.303(19) . 1_655 ?
O11 Fe1 O12 94.61(2) . 1_655 ?
O2 Fe1 O1 89.66(2) . 1_655 ?
O3 Fe1 O1 95.37(2) 1_655 1_655 ?
O14 Fe1 O1 90.68(2) . 1_655 ?
O11 Fe1 O1 175.360(19) . 1_655 ?
O12 Fe1 O1 85.59(2) 1_655 1_655 ?
O13 S1 O11 112.33(3) . 2_665 ?
O13 S1 O12 112.83(3) . . ?
O11 S1 O12 112.30(3) 2_665 . ?
O13 S1 C1 105.31(3) . . ?
O11 S1 C1 108.45(3) 2_665 . ?
O12 S1 C1 105.00(3) . . ?
S1 O11 Fe1 151.96(3) 2_665 . ?
S1 O12 Fe1 139.51(3) . 1_455 ?
C3 C1 C2 120.83(6) . 1_554 ?
C3 C1 S1 120.51(5) . . ?
C2 C1 S1 118.61(5) 1_554 . ?
C3 C2 C1 119.69(6) 2_666 1_556 ?
C3 C2 H2 120.2 2_666 . ?
C1 C2 H2 120.2 1_556 . ?
C1 C3 C2 119.47(6) . 2_666 ?
C1 C3 H3 120.3 . . ?
C2 C3 H3 120.3 2_666 . ?
O16 S2 O15 114.68(4) . . ?
O16 S2 O14 112.01(4) . . ?
O15 S2 O14 111.62(4) . . ?
O16 S2 C4 106.14(3) . . ?
O15 S2 C4 106.17(3) . . ?
O14 S2 C4 105.45(3) . . ?
S2 O14 Fe1 151.59(3) . . ?
C5 C4 C6 120.66(6) . 1_655 ?
C5 C4 S2 119.90(5) . . ?
C6 C4 S2 119.43(5) 1_655 . ?
C4 C5 C6 119.68(6) . 2_666 ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 2_666 . ?
C4 C6 C5 119.66(6) 1_455 2_666 ?
C4 C6 H6 120.2 1_455 . ?
C5 C6 H6 120.2 2_666 . ?
C11 O1 Fe1 132.55(5) . 1_455 ?
O1 C11 N1 123.91(6) . . ?
O1 C11 C12 127.51(6) . . ?
N1 C11 C12 108.57(6) . . ?
C11 C12 C13 104.60(6) . . ?
C11 C12 H12A 110.8 . . ?
C13 C12 H12A 110.8 . . ?
C11 C12 H12B 110.8 . . ?
C13 C12 H12B 110.8 . . ?
H12A C12 H12B 108.9 . . ?
C12 C13 C14 104.32(6) . . ?
C12 C13 H13A 110.9 . . ?
C14 C13 H13A 110.9 . . ?
C12 C13 H13B 110.9 . . ?
C14 C13 H13B 110.9 . . ?
H13A C13 H13B 108.9 . . ?
N1 C14 C13 103.11(6) . . ?
N1 C14 H14A 111.1 . . ?
C13 C14 H14A 111.1 . . ?
N1 C14 H14B 111.1 . . ?
C13 C14 H14B 111.1 . . ?
H14A C14 H14B 109.1 . . ?
C11 N1 C15 124.77(6) . . ?
C11 N1 C14 114.23(6) . . ?
C15 N1 C14 120.77(6) . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 O2 Fe1 138.07(5) . . ?
O2 C21 N2 122.95(7) . . ?
O2 C21 C22 127.37(6) . . ?
N2 C21 C22 109.69(6) . . ?
C21 C22 C23 104.29(7) . . ?
C21 C22 H22A 110.9 . . ?
C23 C22 H22A 110.9 . . ?
C21 C22 H22B 110.9 . . ?
C23 C22 H22B 110.9 . . ?
H22A C22 H22B 108.9 . . ?
C22 C23 C24 105.18(7) . . ?
C22 C23 H23A 110.7 . . ?
C24 C23 H23A 110.7 . . ?
C22 C23 H23B 110.7 . . ?
C24 C23 H23B 110.7 . . ?
H23A C23 H23B 108.8 . . ?
N2 C24 C23 103.63(6) . . ?
N2 C24 H24A 111.0 . . ?
C23 C24 H24A 111.0 . . ?
N2 C24 H24B 111.0 . . ?
C23 C24 H24B 111.0 . . ?
H24A C24 H24B 109.0 . . ?
C21 N2 C25 123.91(6) . . ?
C21 N2 C24 114.08(7) . . ?
C25 N2 C24 121.99(6) . . ?
N2 C25 H25A 109.5 . . ?
N2 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N2 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C31 O3 Fe1 134.89(4) . 1_455 ?
O3 C31 N3 122.73(6) . . ?
O3 C31 C32 127.92(6) . 1_455 ?
N3 C31 C32 109.34(5) . 1_455 ?
C31 C32 C33 104.43(5) 1_655 1_645 ?
C31 C32 H32A 110.9 1_655 . ?
C33 C32 H32A 110.9 1_645 . ?
C31 C32 H32B 110.9 1_655 . ?
C33 C32 H32B 110.9 1_645 . ?
H32A C32 H32B 108.9 . . ?
C34 C33 C32 104.79(5) 1_565 1_465 ?
C34 C33 H33A 110.8 1_565 . ?
C32 C33 H33A 110.8 1_465 . ?
C34 C33 H33B 110.8 1_565 . ?
C32 C33 H33B 110.8 1_465 . ?
H33A C33 H33B 108.9 . . ?
N3 C34 C33 103.66(5) . 1_545 ?
N3 C34 H34A 111.0 . . ?
C33 C34 H34A 111.0 1_545 . ?
N3 C34 H34B 111.0 . . ?
C33 C34 H34B 111.0 1_545 . ?
H34A C34 H34B 109.0 . . ?
C31 N3 C35 123.94(6) . . ?
C31 N3 C34 113.95(6) . . ?
C35 N3 C34 121.44(6) . . ?
N3 C35 H35A 109.5 . . ?
N3 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
N3 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 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
O13 S1 O12 Fe1 123.59(5) . . . 1_455 ?
O11 S1 O12 Fe1 -4.60(6) 2_665 . . 1_455 ?
C1 S1 O12 Fe1 -122.25(5) . . . 1_455 ?
O13 S1 C1 C3 119.72(6) . . . . ?
O11 S1 C1 C3 -119.84(5) 2_665 . . . ?
O12 S1 C1 C3 0.40(6) . . . . ?
O13 S1 C1 C2 -57.73(6) . . . 1_554 ?
O11 S1 C1 C2 62.70(6) 2_665 . . 1_554 ?
O12 S1 C1 C2 -177.06(5) . . . 1_554 ?
C2 C1 C3 C2 -0.25(11) 1_554 . . 2_666 ?
S1 C1 C3 C2 -177.65(5) . . . 2_666 ?
O16 S2 O14 Fe1 123.67(8) . . . . ?
O15 S2 O14 Fe1 -106.20(8) . . . . ?
C4 S2 O14 Fe1 8.66(9) . . . . ?
O16 S2 C4 C5 -10.72(7) . . . . ?
O15 S2 C4 C5 -133.16(6) . . . . ?
O14 S2 C4 C5 108.27(6) . . . . ?
O16 S2 C4 C6 170.74(6) . . . 1_655 ?
O15 S2 C4 C6 48.30(7) . . . 1_655 ?
O14 S2 C4 C6 -70.27(6) . . . 1_655 ?
C6 C4 C5 C6 -0.02(12) 1_655 . . 2_666 ?
S2 C4 C5 C6 -178.55(5) . . . 2_666 ?
Fe1 O1 C11 N1 170.68(5) 1_455 . . . ?
Fe1 O1 C11 C12 -8.09(11) 1_455 . . . ?
O1 C11 C12 C13 -168.69(7) . . . . ?
N1 C11 C12 C13 12.40(8) . . . . ?
C11 C12 C13 C14 -21.07(8) . . . . ?
C12 C13 C14 N1 21.88(8) . . . . ?
O1 C11 N1 C15 -2.19(11) . . . . ?
C12 C11 N1 C15 176.77(7) . . . . ?
O1 C11 N1 C14 -176.81(6) . . . . ?
C12 C11 N1 C14 2.16(8) . . . . ?
C13 C14 N1 C11 -15.63(8) . . . . ?
C13 C14 N1 C15 169.52(7) . . . . ?
Fe1 O2 C21 N2 174.18(5) . . . . ?
Fe1 O2 C21 C22 -5.77(11) . . . . ?
O2 C21 C22 C23 167.90(8) . . . . ?
N2 C21 C22 C23 -12.06(9) . . . . ?
C21 C22 C23 C24 17.18(10) . . . . ?
C22 C23 C24 N2 -16.33(10) . . . . ?
O2 C21 N2 C25 2.73(11) . . . . ?
C22 C21 N2 C25 -177.32(7) . . . . ?
O2 C21 N2 C24 -178.50(7) . . . . ?
C22 C21 N2 C24 1.46(8) . . . . ?
C23 C24 N2 C21 9.64(9) . . . . ?
C23 C24 N2 C25 -171.56(8) . . . . ?
Fe1 O3 C31 N3 -177.51(5) 1_455 . . . ?
Fe1 O3 C31 C32 3.50(12) 1_455 . . 1_455 ?
O3 C31 N3 C35 -5.17(12) . . . . ?
C32 C31 N3 C35 173.98(8) 1_455 . . . ?
O3 C31 N3 C34 -175.92(7) . . . . ?
C32 C31 N3 C34 3.23(9) 1_455 . . . ?
C33 C34 N3 C31 -14.51(9) 1_545 . . . ?
C33 C34 N3 C35 174.49(8) 1_545 . . . ?

_refine_diff_density_max         1.661
_refine_diff_density_min         -0.737
_refine_diff_density_rms         0.062

_shelxl_version_number           2013-4


_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_c:\cz426\cz426
_database_code_depnum_ccdc_archive 'CCDC 967023'
_audit_update_record             
;
2015-03-13 deposited with the CCDC.
2015-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_common            
(cobalt(II)-benzenedisulfonate)(N-methylpyrrolidone)
_chemical_formula_moiety         'C21 H31 Co N3 O9 S2'
_chemical_formula_sum            'C21 H31 Co N3 O9 S2'
_chemical_formula_weight         592.54

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'
Co Co 0.3494 0.9721 '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      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                   9.1132(11)
_cell_length_b                   9.5953(12)
_cell_length_c                   14.2855(17)
_cell_angle_alpha                94.791(5)
_cell_angle_beta                 98.229(5)
_cell_angle_gamma                91.873(6)
_cell_volume                     1230.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9563
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      40.02

_exptl_crystal_description       plates
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_F_000             618
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.264
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.078
_exptl_absorpt_coefficient_mu    0.924
_shelx_estimated_absorpt_T_min   0.792
_shelx_estimated_absorpt_T_max   0.931
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7925
_exptl_absorpt_correction_T_max  0.9314
_exptl_absorpt_process_details   'Bruker SAINT'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            63891
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.132
_diffrn_reflns_theta_max         37.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             12950
_reflns_number_gt                11020
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0353P)²+0.3169P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         12950
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0720
_refine_ls_wR_factor_gt          0.0684
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.98800(2) 0.51556(2) 0.17603(2) 0.00780(2) Uani 1 1 d . . . . .
S1 S 0.20461(2) 0.65069(2) 0.03101(2) 0.00785(3) Uani 1 1 d . . . . .
O11 O 0.90977(6) 0.39072(6) 0.04969(4) 0.01143(9) Uani 1 1 d . . . . .
O13 O 0.24561(7) 0.79873(6) 0.03770(5) 0.01560(11) Uani 1 1 d . . . . .
O12 O 0.16649(6) 0.60509(7) 0.12003(4) 0.01309(10) Uani 1 1 d . . . . .
C1 C 0.36890(8) 0.56309(8) 0.01324(5) 0.00880(10) Uani 1 1 d . . . . .
C2 C 0.43824(8) 0.59112(8) 0.93550(5) 0.01151(12) Uani 1 1 d . . . . .
H2 H 0.3959 0.6533 0.8918 0.014 Uiso 1 1 calc R U . . .
C3 C 0.43004(8) 0.47246(8) 0.07779(5) 0.01133(12) Uani 1 1 d . . . . .
H3 H 0.3823 0.4540 0.1306 0.014 Uiso 1 1 calc R U . . .
S2 S 0.76617(2) 0.37704(2) 0.32517(2) 0.01137(3) Uani 1 1 d . . . . .
O14 O 0.82048(7) 0.42665(7) 0.24140(4) 0.01442(10) Uani 1 1 d . . . . .
O15 O 0.76839(9) 0.22589(7) 0.32421(5) 0.02124(13) Uani 1 1 d . . . . .
O16 O 0.62587(7) 0.43551(8) 0.33987(5) 0.01998(13) Uani 1 1 d . . . . .
C4 C 0.89684(9) 0.44527(8) 0.42402(5) 0.01140(12) Uani 1 1 d . . . . .
C5 C 0.85913(9) 0.55423(9) 0.48572(5) 0.01398(13) Uani 1 1 d . . . . .
H5 H 0.7631 0.5908 0.4757 0.017 Uiso 1 1 calc R U . . .
C6 C 0.03719(9) 0.39076(9) 0.43795(5) 0.01441(13) Uani 1 1 d . . . . .
H6 H 0.0620 0.3165 0.3956 0.017 Uiso 1 1 calc R U . . .
O1 O 0.05780(6) 0.65300(6) 0.30030(4) 0.01216(9) Uani 1 1 d . . . . .
C11 C 0.18142(8) 0.68572(8) 0.34776(5) 0.01042(11) Uani 1 1 d . . . . .
C12 C 0.32780(9) 0.62378(10) 0.33547(6) 0.01818(15) Uani 1 1 d . . . . .
H12A H 0.3636 0.6539 0.2778 0.022 Uiso 1 1 calc R U . . .
H12B H 0.3190 0.5202 0.3306 0.022 Uiso 1 1 calc R U . . .
C13 C 0.43276(10) 0.68065(10) 0.42516(6) 0.01769(14) Uani 1 1 d . . . . .
H13A H 0.5327 0.7045 0.4099 0.021 Uiso 1 1 calc R U . . .
H13B H 0.4419 0.6112 0.4730 0.021 Uiso 1 1 calc R U . . .
C14 C 0.35927(9) 0.81219(9) 0.46164(6) 0.01554(13) Uani 1 1 d . . . . .
H14A H 0.3694 0.8212 0.5318 0.019 Uiso 1 1 calc R U . . .
H14B H 0.4031 0.8977 0.4403 0.019 Uiso 1 1 calc R U . . .
N1 N 0.20427(8) 0.78804(7) 0.41915(5) 0.01232(11) Uani 1 1 d . . . . .
C15 C 0.09194(10) 0.87840(10) 0.44794(6) 0.01823(15) Uani 1 1 d . . . . .
H15A H 0.0943 0.8806 0.5168 0.022 Uiso 1 1 calc R U . . .
H15B H -0.0060 0.8427 0.4159 0.022 Uiso 1 1 calc R U . . .
H15C H 0.1113 0.9733 0.4306 0.022 Uiso 1 1 calc R U . . .
O2 O 0.85359(6) 0.66471(6) 0.12148(4) 0.01222(9) Uani 1 1 d . . . . .
C21 C 0.76102(8) 0.74402(8) 0.15013(5) 0.01119(11) Uani 1 1 d . . . . .
C22 C 0.70097(10) 0.74680(9) 0.24325(6) 0.01648(14) Uani 1 1 d . . . . .
H22A H 0.7823 0.7445 0.2969 0.020 Uiso 1 1 calc R U . . .
H22B H 0.6304 0.6662 0.2436 0.020 Uiso 1 1 calc R U . . .
C23 C 0.62236(13) 0.88494(11) 0.24952(9) 0.0283(2) Uani 1 1 d . . . . .
H23A H 0.6858 0.9576 0.2911 0.034 Uiso 1 1 calc R U . . .
H23B H 0.5276 0.8726 0.2748 0.034 Uiso 1 1 calc R U . . .
C24 C 0.59435(10) 0.92550(10) 0.14650(8) 0.02231(17) Uani 1 1 d . . . . .
H24A H 0.4906 0.9011 0.1171 0.027 Uiso 1 1 calc R U . . .
H24B H 0.6151 1.0269 0.1440 0.027 Uiso 1 1 calc R U . . .
N2 N 0.69858(8) 0.84260(8) 0.09926(5) 0.01553(12) Uani 1 1 d . . . . .
C25 C 0.72591(11) 0.86395(10) 0.00389(7) 0.02173(17) Uani 1 1 d . . . . .
H25A H 0.7659 0.9597 0.0025 0.026 Uiso 1 1 calc R U . . .
H25B H 0.6327 0.8493 -0.0401 0.026 Uiso 1 1 calc R U . . .
H25C H 0.7976 0.7973 -0.0152 0.026 Uiso 1 1 calc R U . . .
O3 O 0.13218(7) 0.36112(6) 0.21736(4) 0.01333(10) Uani 1 1 d . . . . .
C31 C 0.12165(8) 0.23057(8) 0.21057(5) 0.01018(11) Uani 1 1 d . . . . .
C32 C 0.99302(9) 0.13571(8) 0.16193(6) 0.01431(13) Uani 1 1 d . . . . .
H32A H 0.9829 0.1372 0.0921 0.017 Uiso 1 1 calc R U . . .
H32B H 0.8990 0.1641 0.1834 0.017 Uiso 1 1 calc R U . . .
C33 C 0.03303(10) 0.99028(9) 0.19173(7) 0.01739(14) Uani 1 1 d . . . . .
H33A H -0.0210 0.9653 0.2438 0.021 Uiso 1 1 calc R U . . .
H33B H 0.0083 0.9183 0.1374 0.021 Uiso 1 1 calc R U . . .
C34 C 0.20040(9) 0.00222(8) 0.22503(6) 0.01458(13) Uani 1 1 d . . . . .
H34A H 0.2271 -0.0486 0.2822 0.017 Uiso 1 1 calc R U . . .
H34B H 0.2557 -0.0354 0.1744 0.017 Uiso 1 1 calc R U . . .
N3 N 0.23113(8) 0.15251(7) 0.24660(5) 0.01375(11) Uani 1 1 d . . . . .
C35 C 0.37682(11) 0.20861(10) 0.28953(9) 0.0260(2) Uani 1 1 d . . . . .
H35A H 0.3953 0.1870 0.3559 0.031 Uiso 1 1 calc R U . . .
H35B H 0.3817 0.3103 0.2868 0.031 Uiso 1 1 calc R U . . .
H35C H 0.4521 0.1665 0.2550 0.031 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
Co1 O2 2.0453(6) . ?
Co1 O3 2.0790(6) 1_655 ?
Co1 O14 2.0944(6) . ?
Co1 O11 2.1013(6) . ?
Co1 O12 2.1023(6) 1_655 ?
Co1 O1 2.1275(6) 1_655 ?
S1 O13 1.4487(6) . ?
S1 O11 1.4580(6) 2_665 ?
S1 O12 1.4625(6) . ?
S1 C1 1.7799(7) . ?
O11 S1 1.4580(6) 2_665 ?
O12 Co1 2.1024(6) 1_455 ?
C1 C3 1.3913(10) . ?
C1 C2 1.3944(10) 1_554 ?
C2 C3 1.3939(11) 2_666 ?
C2 C1 1.3945(10) 1_556 ?
C2 H2 0.9500 . ?
C3 C2 1.3939(11) 2_666 ?
C3 H3 0.9500 . ?
S2 O16 1.4483(7) . ?
S2 O15 1.4501(7) . ?
S2 O14 1.4672(6) . ?
S2 C4 1.7760(8) . ?
C4 C6 1.3918(12) 1_655 ?
C4 C5 1.3944(11) . ?
C5 C6 1.3917(11) 2_666 ?
C5 H5 0.9500 . ?
C6 C5 1.3917(11) 2_666 ?
C6 C4 1.3918(12) 1_455 ?
C6 H6 0.9500 . ?
O1 C11 1.2450(9) . ?
O1 Co1 2.1274(6) 1_455 ?
C11 N1 1.3439(10) . ?
C11 C12 1.5050(11) . ?
C12 C13 1.5338(12) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.5358(13) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N1 1.4584(11) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
N1 C15 1.4449(11) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O2 C21 1.2438(9) . ?
C21 N2 1.3335(10) . ?
C21 C22 1.5077(11) . ?
C22 C23 1.5293(13) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.5418(16) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 N2 1.4606(12) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
N2 C25 1.4493(12) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
O3 C31 1.2478(9) . ?
O3 Co1 2.0791(6) 1_455 ?
C31 N3 1.3371(10) . ?
C31 C32 1.5090(11) 1_455 ?
C32 C31 1.5090(11) 1_655 ?
C32 C33 1.5328(12) 1_645 ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.5290(12) 1_565 ?
C33 C32 1.5329(12) 1_465 ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 N3 1.4587(10) . ?
C34 C33 1.5290(12) 1_545 ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
N3 C35 1.4470(12) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Co1 O3 173.87(2) . 1_655 ?
O2 Co1 O14 92.88(3) . . ?
O3 Co1 O14 91.54(3) 1_655 . ?
O2 Co1 O11 86.09(2) . . ?
O3 Co1 O11 89.67(2) 1_655 . ?
O14 Co1 O11 89.86(2) . . ?
O2 Co1 O12 89.85(3) . 1_655 ?
O3 Co1 O12 85.99(3) 1_655 1_655 ?
O14 Co1 O12 175.78(2) . 1_655 ?
O11 Co1 O12 93.54(2) . 1_655 ?
O2 Co1 O1 89.95(2) . 1_655 ?
O3 Co1 O1 94.27(2) 1_655 1_655 ?
O14 Co1 O1 90.36(2) . 1_655 ?
O11 Co1 O1 176.05(2) . 1_655 ?
O12 Co1 O1 86.42(2) 1_655 1_655 ?
O13 S1 O11 112.11(4) . 2_665 ?
O13 S1 O12 112.74(4) . . ?
O11 S1 O12 112.53(4) 2_665 . ?
O13 S1 C1 105.48(4) . . ?
O11 S1 C1 108.50(3) 2_665 . ?
O12 S1 C1 104.88(3) . . ?
S1 O11 Co1 151.31(4) 2_665 . ?
S1 O12 Co1 140.77(4) . 1_455 ?
C3 C1 C2 120.65(7) . 1_554 ?
C3 C1 S1 120.53(5) . . ?
C2 C1 S1 118.78(5) 1_554 . ?
C3 C2 C1 119.70(7) 2_666 1_556 ?
C3 C2 H2 120.1 2_666 . ?
C1 C2 H2 120.1 1_556 . ?
C1 C3 C2 119.65(7) . 2_666 ?
C1 C3 H3 120.2 . . ?
C2 C3 H3 120.2 2_666 . ?
O16 S2 O15 114.78(4) . . ?
O16 S2 O14 111.89(4) . . ?
O15 S2 O14 111.53(4) . . ?
O16 S2 C4 105.98(4) . . ?
O15 S2 C4 106.20(4) . . ?
O14 S2 C4 105.70(4) . . ?
S2 O14 Co1 151.15(4) . . ?
C6 C4 C5 120.71(7) 1_655 . ?
C6 C4 S2 119.39(6) 1_655 . ?
C5 C4 S2 119.89(6) . . ?
C6 C5 C4 119.72(8) 2_666 . ?
C6 C5 H5 120.1 2_666 . ?
C4 C5 H5 120.1 . . ?
C5 C6 C4 119.57(7) 2_666 1_455 ?
C5 C6 H6 120.2 2_666 . ?
C4 C6 H6 120.2 1_455 . ?
C11 O1 Co1 133.10(5) . 1_455 ?
O1 C11 N1 123.73(7) . . ?
O1 C11 C12 127.57(7) . . ?
N1 C11 C12 108.69(7) . . ?
C11 C12 C13 104.36(7) . . ?
C11 C12 H12A 110.9 . . ?
C13 C12 H12A 110.9 . . ?
C11 C12 H12B 110.9 . . ?
C13 C12 H12B 110.9 . . ?
H12A C12 H12B 108.9 . . ?
C12 C13 C14 104.27(7) . . ?
C12 C13 H13A 110.9 . . ?
C14 C13 H13A 110.9 . . ?
C12 C13 H13B 110.9 . . ?
C14 C13 H13B 110.9 . . ?
H13A C13 H13B 108.9 . . ?
N1 C14 C13 103.21(7) . . ?
N1 C14 H14A 111.1 . . ?
C13 C14 H14A 111.1 . . ?
N1 C14 H14B 111.1 . . ?
C13 C14 H14B 111.1 . . ?
H14A C14 H14B 109.1 . . ?
C11 N1 C15 125.01(7) . . ?
C11 N1 C14 114.09(7) . . ?
C15 N1 C14 120.64(7) . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 O2 Co1 136.71(5) . . ?
O2 C21 N2 122.96(7) . . ?
O2 C21 C22 127.74(7) . . ?
N2 C21 C22 109.30(7) . . ?
C21 C22 C23 104.23(7) . . ?
C21 C22 H22A 110.9 . . ?
C23 C22 H22A 110.9 . . ?
C21 C22 H22B 110.9 . . ?
C23 C22 H22B 110.9 . . ?
H22A C22 H22B 108.9 . . ?
C22 C23 C24 104.73(8) . . ?
C22 C23 H23A 110.8 . . ?
C24 C23 H23A 110.8 . . ?
C22 C23 H23B 110.8 . . ?
C24 C23 H23B 110.8 . . ?
H23A C23 H23B 108.9 . . ?
N2 C24 C23 103.40(7) . . ?
N2 C24 H24A 111.1 . . ?
C23 C24 H24A 111.1 . . ?
N2 C24 H24B 111.1 . . ?
C23 C24 H24B 111.1 . . ?
H24A C24 H24B 109.0 . . ?
C21 N2 C25 123.73(7) . . ?
C21 N2 C24 114.19(7) . . ?
C25 N2 C24 122.05(7) . . ?
N2 C25 H25A 109.5 . . ?
N2 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N2 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C31 O3 Co1 133.88(5) . 1_455 ?
O3 C31 N3 122.64(7) . . ?
O3 C31 C32 128.16(7) . 1_455 ?
N3 C31 C32 109.19(7) . 1_455 ?
C31 C32 C33 104.10(6) 1_655 1_645 ?
C31 C32 H32A 110.9 1_655 . ?
C33 C32 H32A 110.9 1_645 . ?
C31 C32 H32B 110.9 1_655 . ?
C33 C32 H32B 110.9 1_645 . ?
H32A C32 H32B 109.0 . . ?
C34 C33 C32 104.85(6) 1_565 1_465 ?
C34 C33 H33A 110.8 1_565 . ?
C32 C33 H33A 110.8 1_465 . ?
C34 C33 H33B 110.8 1_565 . ?
C32 C33 H33B 110.8 1_465 . ?
H33A C33 H33B 108.9 . . ?
N3 C34 C33 103.47(6) . 1_545 ?
N3 C34 H34A 111.1 . . ?
C33 C34 H34A 111.1 1_545 . ?
N3 C34 H34B 111.1 . . ?
C33 C34 H34B 111.1 1_545 . ?
H34A C34 H34B 109.0 . . ?
C31 N3 C35 124.00(7) . . ?
C31 N3 C34 113.88(7) . . ?
C35 N3 C34 121.37(7) . . ?
N3 C35 H35A 109.5 . . ?
N3 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
N3 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 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
O13 S1 O12 Co1 119.03(6) . . . 1_455 ?
O11 S1 O12 Co1 -8.97(7) 2_665 . . 1_455 ?
C1 S1 O12 Co1 -126.72(6) . . . 1_455 ?
O13 S1 C1 C3 120.15(7) . . . . ?
O11 S1 C1 C3 -119.56(6) 2_665 . . . ?
O12 S1 C1 C3 0.90(7) . . . . ?
O13 S1 C1 C2 -57.41(7) . . . 1_554 ?
O11 S1 C1 C2 62.89(7) 2_665 . . 1_554 ?
O12 S1 C1 C2 -176.65(6) . . . 1_554 ?
C2 C1 C3 C2 -0.11(13) 1_554 . . 2_666 ?
S1 C1 C3 C2 -177.62(6) . . . 2_666 ?
O16 S2 O14 Co1 129.24(9) . . . . ?
O15 S2 O14 Co1 -100.66(9) . . . . ?
C4 S2 O14 Co1 14.33(10) . . . . ?
O16 S2 C4 C6 169.84(7) . . . 1_655 ?
O15 S2 C4 C6 47.34(7) . . . 1_655 ?
O14 S2 C4 C6 -71.26(7) . . . 1_655 ?
O16 S2 C4 C5 -11.36(7) . . . . ?
O15 S2 C4 C5 -133.86(7) . . . . ?
O14 S2 C4 C5 107.54(7) . . . . ?
C6 C4 C5 C6 0.03(13) 1_655 . . 2_666 ?
S2 C4 C5 C6 -178.76(6) . . . 2_666 ?
Co1 O1 C11 N1 172.17(5) 1_455 . . . ?
Co1 O1 C11 C12 -6.31(12) 1_455 . . . ?
O1 C11 C12 C13 -168.14(8) . . . . ?
N1 C11 C12 C13 13.20(9) . . . . ?
C11 C12 C13 C14 -21.68(9) . . . . ?
C12 C13 C14 N1 22.19(9) . . . . ?
O1 C11 N1 C15 -3.16(12) . . . . ?
C12 C11 N1 C15 175.57(8) . . . . ?
O1 C11 N1 C14 -177.26(7) . . . . ?
C12 C11 N1 C14 1.47(9) . . . . ?
C13 C14 N1 C11 -15.38(9) . . . . ?
C13 C14 N1 C15 170.23(7) . . . . ?
Co1 O2 C21 N2 173.47(6) . . . . ?
Co1 O2 C21 C22 -6.76(13) . . . . ?
O2 C21 C22 C23 166.83(9) . . . . ?
N2 C21 C22 C23 -13.37(10) . . . . ?
C21 C22 C23 C24 19.64(10) . . . . ?
C22 C23 C24 N2 -18.97(10) . . . . ?
O2 C21 N2 C25 3.02(13) . . . . ?
C22 C21 N2 C25 -176.80(8) . . . . ?
O2 C21 N2 C24 -179.20(8) . . . . ?
C22 C21 N2 C24 0.98(10) . . . . ?
C23 C24 N2 C21 11.70(10) . . . . ?
C23 C24 N2 C25 -170.48(8) . . . . ?
Co1 O3 C31 N3 -177.52(6) 1_455 . . . ?
Co1 O3 C31 C32 3.64(13) 1_455 . . 1_455 ?
O3 C31 N3 C35 -5.62(13) . . . . ?
C32 C31 N3 C35 173.42(9) 1_455 . . . ?
O3 C31 N3 C34 -175.84(7) . . . . ?
C32 C31 N3 C34 3.20(9) 1_455 . . . ?
C33 C34 N3 C31 -15.49(9) 1_545 . . . ?
C33 C34 N3 C35 174.01(9) 1_545 . . . ?

_refine_diff_density_max         1.032
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.068

_shelxl_version_number           2013-4


_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_c:\cz466\cz466
_database_code_depnum_ccdc_archive 'CCDC 967024'
_audit_update_record             
;
2015-03-13 deposited with the CCDC.
2015-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_common            
(manganese(II)-benzenedisulfonate)(N-methylpyrrolidone)
_chemical_formula_moiety         'C21 H31 Mn N3 O9 S2'
_chemical_formula_sum            'C21 H31 Mn N3 O9 S2'
_chemical_formula_weight         588.55

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      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                   9.1684(3)
_cell_length_b                   9.6557(3)
_cell_length_c                   14.3787(5)
_cell_angle_alpha                95.2967(17)
_cell_angle_beta                 97.8338(17)
_cell_angle_gamma                92.5755(17)
_cell_volume                     1253.51(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9875
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      36.30

_exptl_crystal_description       plates
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_F_000             614
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.749
_shelx_estimated_absorpt_T_min   0.841
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8406
_exptl_absorpt_correction_T_max  0.9706
_exptl_absorpt_process_details   'Bruker SAINT'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            67956
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.437
_diffrn_reflns_theta_max         36.331
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             12143
_reflns_number_gt                8927
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0375P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         12143
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0745
_refine_ls_wR_factor_gt          0.0701
_refine_ls_goodness_of_fit_ref   0.936
_refine_ls_restrained_S_all      0.936
_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 0.98927(2) 0.51799(2) 0.17601(2) 0.00924(3) Uani 1 1 d . . . . .
S1 S 0.21228(2) 0.65654(2) 0.03108(2) 0.00906(4) Uani 1 1 d . . . . .
O11 O 0.90285(7) 0.38998(7) 0.04699(5) 0.01329(13) Uani 1 1 d . . . . .
O13 O 0.25585(8) 0.80271(7) 0.03323(6) 0.01712(14) Uani 1 1 d . . . . .
O12 O 0.17395(7) 0.61875(8) 0.12130(5) 0.01424(13) Uani 1 1 d . . . . .
C1 C 0.37259(10) 0.56561(10) 0.01374(6) 0.00979(15) Uani 1 1 d . . . . .
C2 C 0.43837(10) 0.58514(10) 0.93358(7) 0.01307(17) Uani 1 1 d . . . . .
H2 H 0.3960 0.6433 0.8886 0.016 Uiso 1 1 calc R U . . .
C3 C 0.43349(10) 0.48120(10) 0.08006(7) 0.01259(17) Uani 1 1 d . . . . .
H3 H 0.3880 0.4688 0.1345 0.015 Uiso 1 1 calc R U . . .
S2 S 0.76373(3) 0.37627(3) 0.32847(2) 0.01323(5) Uani 1 1 d . . . . .
O14 O 0.82109(8) 0.42232(8) 0.24541(5) 0.01747(15) Uani 1 1 d . . . . .
O15 O 0.76114(10) 0.22600(8) 0.32817(6) 0.02392(17) Uani 1 1 d . . . . .
O16 O 0.62635(8) 0.43723(9) 0.34293(6) 0.02276(17) Uani 1 1 d . . . . .
C4 C 0.89526(11) 0.44474(10) 0.42577(7) 0.01297(17) Uani 1 1 d . . . . .
C5 C 0.86119(11) 0.55398(11) 0.48747(7) 0.01580(18) Uani 1 1 d . . . . .
H5 H 0.7664 0.5906 0.4787 0.019 Uiso 1 1 calc R U . . .
C6 C 0.03394(11) 0.39061(11) 0.43807(7) 0.01610(18) Uani 1 1 d . . . . .
H6 H 0.0567 0.3160 0.3956 0.019 Uiso 1 1 calc R U . . .
O1 O 0.06328(8) 0.65847(7) 0.30552(5) 0.01423(13) Uani 1 1 d . . . . .
C11 C 0.18612(11) 0.69048(10) 0.35275(7) 0.01268(17) Uani 1 1 d . . . . .
C12 C 0.32952(11) 0.62459(12) 0.34124(8) 0.0204(2) Uani 1 1 d . . . . .
H12A H 0.3662 0.6499 0.2831 0.024 Uiso 1 1 calc R U . . .
H12B H 0.3172 0.5218 0.3385 0.024 Uiso 1 1 calc R U . . .
C13 C 0.43516(12) 0.68398(12) 0.42896(8) 0.0203(2) Uani 1 1 d . . . . .
H13A H 0.5349 0.7050 0.4129 0.024 Uiso 1 1 calc R U . . .
H13B H 0.4425 0.6175 0.4776 0.024 Uiso 1 1 calc R U . . .
C14 C 0.36628(11) 0.81793(11) 0.46386(7) 0.01796(19) Uani 1 1 d . . . . .
H14A H 0.3767 0.8304 0.5336 0.022 Uiso 1 1 calc R U . . .
H14B H 0.4120 0.9009 0.4411 0.022 Uiso 1 1 calc R U . . .
N1 N 0.21168(9) 0.79383(9) 0.42243(6) 0.01479(16) Uani 1 1 d . . . . .
C15 C 0.10165(13) 0.88505(12) 0.45095(8) 0.0219(2) Uani 1 1 d . . . . .
H15A H 0.1044 0.8897 0.5195 0.026 Uiso 1 1 calc R U . . .
H15B H 0.0038 0.8488 0.4199 0.026 Uiso 1 1 calc R U . . .
H15C H 0.1222 0.9785 0.4327 0.026 Uiso 1 1 calc R U . . .
O2 O 0.84638(8) 0.66839(7) 0.12254(5) 0.01491(14) Uani 1 1 d . . . . .
C21 C 0.75615(10) 0.74866(10) 0.15075(7) 0.01307(17) Uani 1 1 d . . . . .
C22 C 0.70035(12) 0.75532(12) 0.24462(8) 0.0196(2) Uani 1 1 d . . . . .
H22A H 0.7833 0.7628 0.2970 0.024 Uiso 1 1 calc R U . . .
H22B H 0.6364 0.6715 0.2491 0.024 Uiso 1 1 calc R U . . .
C23 C 0.6133(2) 0.88534(16) 0.24760(12) 0.0492(5) Uani 1 1 d . . . . .
H23A H 0.6670 0.9597 0.2931 0.059 Uiso 1 1 calc R U . . .
H23B H 0.5157 0.8648 0.2669 0.059 Uiso 1 1 calc R U . . .
C24 C 0.59545(12) 0.93072(12) 0.14819(9) 0.0253(2) Uani 1 1 d . . . . .
H24A H 0.4922 0.9136 0.1171 0.030 Uiso 1 1 calc R U . . .
H24B H 0.6247 1.0309 0.1492 0.030 Uiso 1 1 calc R U . . .
N2 N 0.69412(10) 0.84434(9) 0.10003(7) 0.01786(17) Uani 1 1 d . . . . .
C25 C 0.72020(14) 0.86287(12) 0.00462(8) 0.0249(2) Uani 1 1 d . . . . .
H25A H 0.7636 0.9570 0.0027 0.030 Uiso 1 1 calc R U . . .
H25B H 0.6266 0.8499 -0.0379 0.030 Uiso 1 1 calc R U . . .
H25C H 0.7881 0.7942 -0.0154 0.030 Uiso 1 1 calc R U . . .
O3 O 0.13733(8) 0.35724(7) 0.21369(5) 0.01597(14) Uani 1 1 d . . . . .
C31 C 0.12540(10) 0.22765(10) 0.20846(7) 0.01147(16) Uani 1 1 d . . . . .
C32 C 0.99505(11) 0.13331(11) 0.16329(8) 0.01762(19) Uani 1 1 d . . . . .
H32A H 0.9810 0.1345 0.0939 0.021 Uiso 1 1 calc R U . . .
H32B H 0.9038 0.1621 0.1875 0.021 Uiso 1 1 calc R U . . .
C33 C 0.03339(12) 0.98866(11) 0.19077(9) 0.0214(2) Uani 1 1 d . . . . .
H33A H 0.0080 0.9176 0.1361 0.026 Uiso 1 1 calc R U . . .
H33B H -0.0205 0.9629 0.2424 0.026 Uiso 1 1 calc R U . . .
C34 C 0.20009(11) 0.00056(10) 0.22331(8) 0.01695(19) Uani 1 1 d . . . . .
H34A H 0.2256 -0.0477 0.2807 0.020 Uiso 1 1 calc R U . . .
H34B H 0.2544 -0.0393 0.1731 0.020 Uiso 1 1 calc R U . . .
N3 N 0.23340(9) 0.15056(9) 0.24300(6) 0.01519(16) Uani 1 1 d . . . . .
C35 C 0.37938(12) 0.20709(12) 0.28382(10) 0.0279(3) Uani 1 1 d . . . . .
H35A H 0.4006 0.1835 0.3489 0.033 Uiso 1 1 calc R U . . .
H35B H 0.3840 0.3086 0.2833 0.033 Uiso 1 1 calc R U . . .
H35C H 0.4524 0.1674 0.2468 0.033 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 O2 2.1257(7) . ?
Mn1 O11 2.1645(7) . ?
Mn1 O14 2.1653(7) . ?
Mn1 O3 2.1656(7) 1_655 ?
Mn1 O12 2.1883(7) 1_655 ?
Mn1 O1 2.2078(7) 1_655 ?
S1 O13 1.4458(7) . ?
S1 O11 1.4551(7) 2_665 ?
S1 O12 1.4627(7) . ?
S1 C1 1.7801(9) . ?
O11 S1 1.4551(7) 2_665 ?
O12 Mn1 2.1883(7) 1_455 ?
C1 C3 1.3873(13) . ?
C1 C2 1.3953(12) 1_554 ?
C2 C3 1.3915(13) 2_666 ?
C2 C1 1.3953(12) 1_556 ?
C2 H2 0.9500 . ?
C3 C2 1.3915(13) 2_666 ?
C3 H3 0.9500 . ?
S2 O16 1.4462(8) . ?
S2 O15 1.4498(8) . ?
S2 O14 1.4659(7) . ?
S2 C4 1.7737(10) . ?
C4 C5 1.3891(14) . ?
C4 C6 1.3917(14) 1_655 ?
C5 C6 1.3871(15) 2_666 ?
C5 H5 0.9500 . ?
C6 C5 1.3871(15) 2_666 ?
C6 C4 1.3916(14) 1_455 ?
C6 H6 0.9500 . ?
O1 C11 1.2436(12) . ?
O1 Mn1 2.2078(7) 1_455 ?
C11 N1 1.3361(13) . ?
C11 C12 1.5085(14) . ?
C12 C13 1.5302(16) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.5374(15) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N1 1.4604(13) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
N1 C15 1.4448(13) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O2 C21 1.2412(11) . ?
C21 N2 1.3294(13) . ?
C21 C22 1.5042(14) . ?
C22 C23 1.5179(17) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.523(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 N2 1.4579(14) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
N2 C25 1.4500(15) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
O3 C31 1.2456(11) . ?
O3 Mn1 2.1655(7) 1_455 ?
C31 N3 1.3348(12) . ?
C31 C32 1.5037(14) 1_455 ?
C32 C31 1.5037(14) 1_655 ?
C32 C33 1.5292(15) 1_645 ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C32 1.5292(15) 1_465 ?
C33 C34 1.5322(15) 1_565 ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 N3 1.4601(13) . ?
C34 C33 1.5322(15) 1_545 ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
N3 C35 1.4473(14) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Mn1 O11 85.08(3) . . ?
O2 Mn1 O14 92.80(3) . . ?
O11 Mn1 O14 89.18(3) . . ?
O2 Mn1 O3 173.39(3) . 1_655 ?
O11 Mn1 O3 89.32(3) . 1_655 ?
O14 Mn1 O3 90.62(3) . 1_655 ?
O2 Mn1 O12 90.52(3) . 1_655 ?
O11 Mn1 O12 96.50(3) . 1_655 ?
O14 Mn1 O12 173.65(3) . 1_655 ?
O3 Mn1 O12 86.61(3) 1_655 1_655 ?
O2 Mn1 O1 90.79(3) . 1_655 ?
O11 Mn1 O1 175.70(3) . 1_655 ?
O14 Mn1 O1 89.83(3) . 1_655 ?
O3 Mn1 O1 94.87(3) 1_655 1_655 ?
O12 Mn1 O1 84.72(3) 1_655 1_655 ?
O13 S1 O11 112.41(4) . 2_665 ?
O13 S1 O12 112.92(4) . . ?
O11 S1 O12 111.99(4) 2_665 . ?
O13 S1 C1 105.66(4) . . ?
O11 S1 C1 108.03(4) 2_665 . ?
O12 S1 C1 105.24(4) . . ?
S1 O11 Mn1 153.00(4) 2_665 . ?
S1 O12 Mn1 138.78(5) . 1_455 ?
C3 C1 C2 120.85(8) . 1_554 ?
C3 C1 S1 120.70(7) . . ?
C2 C1 S1 118.41(7) 1_554 . ?
C3 C2 C1 119.54(9) 2_666 1_556 ?
C3 C2 H2 120.2 2_666 . ?
C1 C2 H2 120.2 1_556 . ?
C1 C3 C2 119.61(8) . 2_666 ?
C1 C3 H3 120.2 . . ?
C2 C3 H3 120.2 2_666 . ?
O16 S2 O15 114.77(5) . . ?
O16 S2 O14 112.21(5) . . ?
O15 S2 O14 111.56(5) . . ?
O16 S2 C4 106.21(5) . . ?
O15 S2 C4 106.30(5) . . ?
O14 S2 C4 104.95(4) . . ?
S2 O14 Mn1 152.92(5) . . ?
C5 C4 C6 120.45(9) . 1_655 ?
C5 C4 S2 120.15(8) . . ?
C6 C4 S2 119.38(8) 1_655 . ?
C6 C5 C4 119.78(9) 2_666 . ?
C6 C5 H5 120.1 2_666 . ?
C4 C5 H5 120.1 . . ?
C5 C6 C4 119.77(9) 2_666 1_455 ?
C5 C6 H6 120.1 2_666 . ?
C4 C6 H6 120.1 1_455 . ?
C11 O1 Mn1 133.30(6) . 1_455 ?
O1 C11 N1 124.13(9) . . ?
O1 C11 C12 127.19(9) . . ?
N1 C11 C12 108.67(9) . . ?
C11 C12 C13 104.36(8) . . ?
C11 C12 H12A 110.9 . . ?
C13 C12 H12A 110.9 . . ?
C11 C12 H12B 110.9 . . ?
C13 C12 H12B 110.9 . . ?
H12A C12 H12B 108.9 . . ?
C12 C13 C14 104.47(9) . . ?
C12 C13 H13A 110.9 . . ?
C14 C13 H13A 110.9 . . ?
C12 C13 H13B 110.9 . . ?
C14 C13 H13B 110.9 . . ?
H13A C13 H13B 108.9 . . ?
N1 C14 C13 102.83(8) . . ?
N1 C14 H14A 111.2 . . ?
C13 C14 H14A 111.2 . . ?
N1 C14 H14B 111.2 . . ?
C13 C14 H14B 111.2 . . ?
H14A C14 H14B 109.1 . . ?
C11 N1 C15 124.55(9) . . ?
C11 N1 C14 114.40(8) . . ?
C15 N1 C14 120.81(9) . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 O2 Mn1 138.74(7) . . ?
O2 C21 N2 123.54(9) . . ?
O2 C21 C22 126.95(9) . . ?
N2 C21 C22 109.52(8) . . ?
C21 C22 C23 104.49(9) . . ?
C21 C22 H22A 110.9 . . ?
C23 C22 H22A 110.9 . . ?
C21 C22 H22B 110.9 . . ?
C23 C22 H22B 110.9 . . ?
H22A C22 H22B 108.9 . . ?
C22 C23 C24 106.42(10) . . ?
C22 C23 H23A 110.4 . . ?
C24 C23 H23A 110.4 . . ?
C22 C23 H23B 110.4 . . ?
C24 C23 H23B 110.4 . . ?
H23A C23 H23B 108.6 . . ?
N2 C24 C23 103.83(9) . . ?
N2 C24 H24A 111.0 . . ?
C23 C24 H24A 111.0 . . ?
N2 C24 H24B 111.0 . . ?
C23 C24 H24B 111.0 . . ?
H24A C24 H24B 109.0 . . ?
C21 N2 C25 123.75(9) . . ?
C21 N2 C24 114.37(9) . . ?
C25 N2 C24 121.88(9) . . ?
N2 C25 H25A 109.5 . . ?
N2 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N2 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C31 O3 Mn1 134.65(7) . 1_455 ?
O3 C31 N3 123.09(9) . . ?
O3 C31 C32 127.66(9) . 1_455 ?
N3 C31 C32 109.25(8) . 1_455 ?
C31 C32 C33 104.61(8) 1_655 1_645 ?
C31 C32 H32A 110.8 1_655 . ?
C33 C32 H32A 110.8 1_645 . ?
C31 C32 H32B 110.8 1_655 . ?
C33 C32 H32B 110.8 1_645 . ?
H32A C32 H32B 108.9 . . ?
C32 C33 C34 105.02(8) 1_465 1_565 ?
C32 C33 H33A 110.7 1_465 . ?
C34 C33 H33A 110.7 1_565 . ?
C32 C33 H33B 110.7 1_465 . ?
C34 C33 H33B 110.7 1_565 . ?
H33A C33 H33B 108.8 . . ?
N3 C34 C33 103.46(8) . 1_545 ?
N3 C34 H34A 111.1 . . ?
C33 C34 H34A 111.1 1_545 . ?
N3 C34 H34B 111.1 . . ?
C33 C34 H34B 111.1 1_545 . ?
H34A C34 H34B 109.0 . . ?
C31 N3 C35 123.86(9) . . ?
C31 N3 C34 114.08(8) . . ?
C35 N3 C34 121.43(8) . . ?
N3 C35 H35A 109.5 . . ?
N3 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
N3 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 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
O13 S1 O12 Mn1 125.27(7) . . . 1_455 ?
O11 S1 O12 Mn1 -2.83(8) 2_665 . . 1_455 ?
C1 S1 O12 Mn1 -119.95(7) . . . 1_455 ?
O13 S1 C1 C3 119.52(8) . . . . ?
O11 S1 C1 C3 -119.97(8) 2_665 . . . ?
O12 S1 C1 C3 -0.19(9) . . . . ?
O13 S1 C1 C2 -58.26(9) . . . 1_554 ?
O11 S1 C1 C2 62.26(9) 2_665 . . 1_554 ?
O12 S1 C1 C2 -177.96(8) . . . 1_554 ?
C2 C1 C3 C2 -0.16(16) 1_554 . . 2_666 ?
S1 C1 C3 C2 -177.88(8) . . . 2_666 ?
O16 S2 O14 Mn1 123.01(11) . . . . ?
O15 S2 O14 Mn1 -106.60(11) . . . . ?
C4 S2 O14 Mn1 8.10(12) . . . . ?
O16 S2 C4 C5 -10.36(9) . . . . ?
O15 S2 C4 C5 -133.02(8) . . . . ?
O14 S2 C4 C5 108.66(8) . . . . ?
O16 S2 C4 C6 171.42(8) . . . 1_655 ?
O15 S2 C4 C6 48.76(9) . . . 1_655 ?
O14 S2 C4 C6 -69.56(9) . . . 1_655 ?
C6 C4 C5 C6 -0.07(16) 1_655 . . 2_666 ?
S2 C4 C5 C6 -178.28(8) . . . 2_666 ?
Mn1 O1 C11 N1 169.90(7) 1_455 . . . ?
Mn1 O1 C11 C12 -8.69(15) 1_455 . . . ?
O1 C11 C12 C13 -169.02(10) . . . . ?
N1 C11 C12 C13 12.21(11) . . . . ?
C11 C12 C13 C14 -21.12(11) . . . . ?
C12 C13 C14 N1 22.14(11) . . . . ?
O1 C11 N1 C15 -1.77(16) . . . . ?
C12 C11 N1 C15 177.04(9) . . . . ?
O1 C11 N1 C14 -176.27(9) . . . . ?
C12 C11 N1 C14 2.55(12) . . . . ?
C13 C14 N1 C11 -16.01(11) . . . . ?
C13 C14 N1 C15 169.27(9) . . . . ?
Mn1 O2 C21 N2 172.10(7) . . . . ?
Mn1 O2 C21 C22 -7.58(17) . . . . ?
O2 C21 C22 C23 171.16(12) . . . . ?
N2 C21 C22 C23 -8.55(13) . . . . ?
C21 C22 C23 C24 11.60(15) . . . . ?
C22 C23 C24 N2 -10.55(15) . . . . ?
O2 C21 N2 C25 2.38(16) . . . . ?
C22 C21 N2 C25 -177.89(10) . . . . ?
O2 C21 N2 C24 -177.86(10) . . . . ?
C22 C21 N2 C24 1.86(12) . . . . ?
C23 C24 N2 C21 5.62(14) . . . . ?
C23 C24 N2 C25 -174.62(12) . . . . ?
Mn1 O3 C31 N3 -175.45(7) 1_455 . . . ?
Mn1 O3 C31 C32 5.56(16) 1_455 . . 1_455 ?
O3 C31 N3 C35 -4.82(16) . . . . ?
C32 C31 N3 C35 174.34(10) 1_455 . . . ?
O3 C31 N3 C34 -175.81(9) . . . . ?
C32 C31 N3 C34 3.35(12) 1_455 . . . ?
C33 C34 N3 C31 -14.17(12) 1_545 . . . ?
C33 C34 N3 C35 174.60(10) 1_545 . . . ?

_refine_diff_density_max         1.095
_refine_diff_density_min         -0.743
_refine_diff_density_rms         0.068

_shelxl_version_number           2013-4

