# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2007


data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Wonwoo Nam'
_publ_contact_author_address     
;
Deaprtment of Chemistry
Ewha Womans University
Seoul
120-750
SOUTH KOREA
;

_publ_contact_author_email       WWNAM@EWHA.AC.KR

_publ_section_title              
;
A Highly Efficient Non-Heme Manganese Complex in
Oxygenation Reactions
;
loop_
_publ_author_name
'Wonwoo Nam'
'Soo Jeong Kim'
'In Young Kim'
'Youngmee Kim'
'Sung-Jin Kim'
'Jinheung Kim'
'Kasi Nehru'
'Mi Sook Seo'

# Attachment 'Supp-X-ray-revised.cif'

data_yk457sadp212121
_database_code_depnum_ccdc_archive 'CCDC 650716'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H22 F6 Mn N4 O6 S2'
_chemical_formula_weight         695.52

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   9.677(6)
_cell_length_b                   13.617(10)
_cell_length_c                   21.660(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2854(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    1456
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      19.41

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1412
_exptl_absorpt_coefficient_mu    0.695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14719
_diffrn_reflns_av_R_equivalents  0.2424
_diffrn_reflns_av_sigmaI/netI    0.2628
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5588
_reflns_number_gt                2455
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0226P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.20(3)
_refine_ls_number_reflns         5588
_refine_ls_number_parameters     391
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1472
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.0966
_refine_ls_wR_factor_gt          0.0737
_refine_ls_goodness_of_fit_ref   0.807
_refine_ls_restrained_S_all      0.807
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.80677(9) 0.53355(6) 0.87650(4) 0.0349(2) Uani 1 1 d . . .
N1 N 0.6023(4) 0.4634(3) 0.8781(2) 0.0389(11) Uani 1 1 d . . .
N2 N 0.7051(5) 0.5771(3) 0.7831(2) 0.0346(12) Uani 1 1 d . . .
N3 N 0.7203(5) 0.6906(3) 0.9014(2) 0.0361(13) Uani 1 1 d . . .
N4 N 0.9846(5) 0.6322(3) 0.8644(2) 0.0368(13) Uani 1 1 d . . .
C1 C 0.5516(7) 0.4062(5) 0.9243(3) 0.054(2) Uani 1 1 d . . .
H1 H 0.6062 0.3990 0.9605 0.065 Uiso 1 1 calc R . .
C2 C 0.4266(8) 0.3578(6) 0.9223(4) 0.071(2) Uani 1 1 d . . .
H2 H 0.3942 0.3222 0.9572 0.085 Uiso 1 1 calc R . .
C3 C 0.3517(7) 0.3617(5) 0.8705(4) 0.070(2) Uani 1 1 d . . .
H3 H 0.2678 0.3257 0.8679 0.084 Uiso 1 1 calc R . .
C4 C 0.3957(7) 0.4190(5) 0.8194(3) 0.0449(17) Uani 1 1 d . . .
C5 C 0.3187(7) 0.4282(4) 0.7634(3) 0.0538(19) Uani 1 1 d . . .
H5 H 0.2327 0.3952 0.7591 0.065 Uiso 1 1 calc R . .
C6 C 0.3679(6) 0.4841(5) 0.7161(3) 0.056(2) Uani 1 1 d . . .
H6 H 0.3168 0.4905 0.6789 0.067 Uiso 1 1 calc R . .
C7 C 0.4971(6) 0.5330(5) 0.7232(3) 0.0489(17) Uani 1 1 d . . .
H7 H 0.5308 0.5721 0.6901 0.059 Uiso 1 1 calc R . .
C8 C 0.5738(6) 0.5258(4) 0.7753(2) 0.0363(14) Uani 1 1 d . . .
C9 C 0.5239(6) 0.4676(5) 0.8256(3) 0.0392(15) Uani 1 1 d . . .
C10 C 0.6789(7) 0.6854(4) 0.7884(2) 0.0416(16) Uani 1 1 d . . .
H10A H 0.6123 0.7059 0.7562 0.050 Uiso 1 1 calc R . .
H10B H 0.7663 0.7216 0.7815 0.050 Uiso 1 1 calc R . .
C11 C 0.6212(6) 0.7113(4) 0.8521(3) 0.0423(16) Uani 1 1 d . . .
H11A H 0.5966 0.7819 0.8530 0.051 Uiso 1 1 calc R . .
H11B H 0.5357 0.6730 0.8594 0.051 Uiso 1 1 calc R . .
C12 C 0.8347(6) 0.7613(4) 0.9005(2) 0.0353(16) Uani 1 1 d . . .
C13 C 0.8166(7) 0.8579(5) 0.9188(3) 0.0467(17) Uani 1 1 d . . .
H13 H 0.7290 0.8792 0.9334 0.056 Uiso 1 1 calc R . .
C14 C 0.9257(8) 0.9234(5) 0.9159(3) 0.057(2) Uani 1 1 d . . .
H14 H 0.9103 0.9898 0.9274 0.069 Uiso 1 1 calc R . .
C15 C 1.0529(8) 0.8963(5) 0.8975(3) 0.0477(19) Uani 1 1 d . . .
H15 H 1.1258 0.9429 0.8963 0.057 Uiso 1 1 calc R . .
C16 C 1.0775(6) 0.7965(4) 0.8797(3) 0.0367(15) Uani 1 1 d . . .
C17 C 1.2086(7) 0.7631(5) 0.8594(3) 0.0527(19) Uani 1 1 d . . .
H17 H 1.2854 0.8065 0.8580 0.063 Uiso 1 1 calc R . .
C18 C 1.2220(7) 0.6675(6) 0.8419(3) 0.062(2) Uani 1 1 d . . .
H18 H 1.3084 0.6434 0.8276 0.075 Uiso 1 1 calc R . .
C19 C 1.1098(6) 0.6066(5) 0.8450(3) 0.0496(18) Uani 1 1 d . . .
H19 H 1.1224 0.5404 0.8323 0.059 Uiso 1 1 calc R . .
C20 C 0.9670(6) 0.7289(4) 0.8820(3) 0.0341(15) Uani 1 1 d . . .
C21 C 0.7967(6) 0.5612(4) 0.7291(2) 0.0518(18) Uani 1 1 d . . .
H21A H 0.7974 0.4913 0.7184 0.078 Uiso 1 1 calc R . .
H21B H 0.8907 0.5824 0.7394 0.078 Uiso 1 1 calc R . .
H21C H 0.7624 0.5994 0.6940 0.078 Uiso 1 1 calc R . .
C22 C 0.6488(6) 0.6888(4) 0.9619(3) 0.053(2) Uani 1 1 d . . .
H22A H 0.7173 0.6830 0.9950 0.079 Uiso 1 1 calc R . .
H22B H 0.5858 0.6325 0.9634 0.079 Uiso 1 1 calc R . .
H22C H 0.5961 0.7496 0.9673 0.079 Uiso 1 1 calc R . .
S1 S 0.9053(2) 0.49130(14) 1.03098(8) 0.0556(5) Uani 1 1 d . . .
O11 O 0.8410(4) 0.4951(3) 0.97109(17) 0.0619(14) Uani 1 1 d . . .
O12 O 0.8370(6) 0.4237(5) 1.0722(2) 0.122(3) Uani 1 1 d . . .
O13 O 0.9459(6) 0.5830(4) 1.0554(3) 0.114(2) Uani 1 1 d . . .
C111 C 1.0654(9) 0.4300(7) 1.0189(4) 0.076(3) Uani 1 1 d . . .
F11 F 1.1420(5) 0.4810(4) 0.9773(2) 0.133(2) Uani 1 1 d . . .
F12 F 1.1400(5) 0.4223(4) 1.0682(2) 0.119(2) Uani 1 1 d . . .
F13 F 1.0496(5) 0.3417(3) 0.9947(2) 0.114(2) Uani 1 1 d . . .
S2 S 0.90238(19) 0.32262(14) 0.80837(8) 0.0474(5) Uani 1 1 d . . .
O21 O 0.9290(4) 0.4094(3) 0.84476(18) 0.0487(12) Uani 1 1 d . . .
O22 O 0.7651(4) 0.3186(3) 0.7836(2) 0.0733(15) Uani 1 1 d . . .
O23 O 1.0129(5) 0.2981(3) 0.76719(19) 0.0611(14) Uani 1 1 d . . .
C211 C 0.9061(10) 0.2262(5) 0.8653(3) 0.060(2) Uani 1 1 d . . .
F21 F 1.0316(5) 0.2135(3) 0.8885(2) 0.0994(16) Uani 1 1 d . . .
F22 F 0.8697(5) 0.1405(3) 0.8395(2) 0.1049(17) Uani 1 1 d . . .
F23 F 0.8193(6) 0.2428(3) 0.9109(2) 0.0979(16) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Mn1 0.0324(5) 0.0332(5) 0.0390(5) 0.0013(5) 0.0008(5) 0.0005(5)
N1 0.028(3) 0.035(3) 0.054(3) 0.009(3) 0.007(3) 0.002(3)
N2 0.033(3) 0.027(3) 0.043(3) -0.004(2) 0.005(3) -0.003(3)
N3 0.027(3) 0.039(3) 0.042(3) 0.007(2) 0.009(2) 0.001(3)
N4 0.033(3) 0.028(3) 0.049(3) 0.000(3) 0.005(3) 0.002(3)
C1 0.045(4) 0.057(5) 0.061(5) 0.013(4) 0.009(4) -0.001(4)
C2 0.049(5) 0.078(6) 0.085(6) 0.013(5) 0.014(5) -0.022(5)
C3 0.036(4) 0.054(5) 0.120(7) -0.012(5) 0.022(5) -0.015(4)
C4 0.031(4) 0.035(4) 0.069(5) -0.010(3) 0.008(4) 0.005(4)
C5 0.036(4) 0.045(5) 0.080(5) -0.019(4) -0.006(4) -0.009(4)
C6 0.042(4) 0.058(5) 0.067(4) -0.017(4) -0.020(4) -0.008(4)
C7 0.049(4) 0.057(5) 0.040(4) -0.012(4) -0.004(3) -0.015(4)
C8 0.033(3) 0.037(4) 0.039(3) 0.003(3) -0.003(3) -0.003(3)
C9 0.029(4) 0.040(4) 0.049(4) 0.003(4) 0.007(3) 0.011(4)
C10 0.042(4) 0.029(4) 0.054(4) 0.007(3) -0.011(3) -0.019(4)
C11 0.025(3) 0.029(4) 0.073(4) -0.001(3) -0.001(4) -0.002(3)
C12 0.031(4) 0.037(4) 0.038(3) 0.004(3) -0.001(3) -0.006(3)
C13 0.046(4) 0.041(4) 0.053(4) -0.009(3) 0.002(4) 0.006(4)
C14 0.066(5) 0.045(5) 0.061(5) -0.002(4) -0.012(4) 0.002(5)
C15 0.061(5) 0.038(5) 0.045(4) 0.007(3) -0.016(4) -0.011(4)
C16 0.032(4) 0.039(4) 0.039(3) 0.004(3) -0.007(3) -0.009(3)
C17 0.048(5) 0.045(5) 0.065(5) -0.004(4) -0.007(4) -0.017(4)
C18 0.029(4) 0.077(6) 0.080(5) -0.013(4) 0.007(4) -0.002(4)
C19 0.035(4) 0.036(5) 0.078(5) -0.009(3) 0.010(4) -0.005(4)
C20 0.040(4) 0.027(4) 0.035(3) 0.001(3) -0.005(3) -0.005(3)
C21 0.044(4) 0.066(5) 0.045(4) 0.010(3) 0.002(4) 0.000(4)
C22 0.051(5) 0.042(4) 0.065(5) 0.004(4) 0.022(4) 0.003(4)
S1 0.0556(12) 0.0612(14) 0.0500(11) -0.0067(10) -0.0098(10) 0.0121(11)
O11 0.070(3) 0.076(4) 0.040(2) 0.014(2) -0.005(2) 0.033(3)
O12 0.100(4) 0.197(7) 0.071(3) 0.067(4) 0.019(4) -0.023(5)
O13 0.093(5) 0.074(4) 0.174(6) -0.073(4) -0.042(4) 0.032(4)
C111 0.069(6) 0.092(8) 0.068(6) -0.026(5) -0.021(5) 0.019(6)
F11 0.082(4) 0.185(6) 0.133(5) 0.015(4) 0.035(4) 0.029(4)
F12 0.104(4) 0.125(5) 0.130(4) -0.029(3) -0.061(4) 0.049(4)
F13 0.119(4) 0.070(4) 0.153(5) -0.050(3) -0.048(4) 0.029(3)
S2 0.0453(11) 0.0409(12) 0.0560(10) -0.0070(9) 0.0078(10) -0.0012(10)
O21 0.050(3) 0.031(3) 0.065(3) -0.012(2) 0.006(2) 0.003(2)
O22 0.046(3) 0.077(4) 0.096(4) -0.025(3) -0.015(3) 0.006(3)
O23 0.055(3) 0.058(3) 0.071(3) -0.012(3) 0.020(3) -0.001(3)
C211 0.072(6) 0.041(5) 0.067(6) 0.001(4) 0.011(5) -0.002(5)
F21 0.109(4) 0.083(4) 0.106(4) 0.014(3) -0.015(3) 0.019(4)
F22 0.133(5) 0.040(3) 0.142(4) 0.001(3) 0.009(3) -0.035(3)
F23 0.123(4) 0.087(4) 0.084(3) 0.003(3) 0.043(3) -0.030(3)

_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 O11 2.141(4) . ?
Mn1 O21 2.175(4) . ?
Mn1 N1 2.198(5) . ?
Mn1 N4 2.199(5) . ?
Mn1 N2 2.327(5) . ?
Mn1 N3 2.359(5) . ?
N1 C1 1.360(7) . ?
N1 C9 1.368(6) . ?
N2 C8 1.460(7) . ?
N2 C21 1.482(6) . ?
N2 C10 1.502(6) . ?
N3 C11 1.463(7) . ?
N3 C12 1.467(7) . ?
N3 C22 1.483(6) . ?
N4 C19 1.328(7) . ?
N4 C20 1.380(7) . ?
C1 C2 1.379(8) . ?
C1 H1 0.9500 . ?
C2 C3 1.336(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.420(9) . ?
C3 H3 0.9500 . ?
C4 C9 1.412(8) . ?
C4 C5 1.430(8) . ?
C5 C6 1.363(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.425(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.353(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.431(7) . ?
C10 C11 1.529(7) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.384(8) . ?
C12 C20 1.413(8) . ?
C13 C14 1.384(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.346(9) . ?
C14 H14 0.9500 . ?
C15 C16 1.433(8) . ?
C15 H15 0.9500 . ?
C16 C20 1.412(7) . ?
C16 C17 1.418(8) . ?
C17 C18 1.362(8) . ?
C17 H17 0.9500 . ?
C18 C19 1.369(8) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
S1 O13 1.412(5) . ?
S1 O11 1.440(4) . ?
S1 O12 1.442(5) . ?
S1 C111 1.779(8) . ?
C111 F12 1.294(8) . ?
C111 F13 1.321(8) . ?
C111 F11 1.357(9) . ?
S2 O23 1.432(4) . ?
S2 O22 1.434(4) . ?
S2 O21 1.444(4) . ?
S2 C211 1.802(7) . ?
C211 F23 1.315(8) . ?
C211 F21 1.326(8) . ?
C211 F22 1.342(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 Mn1 O21 91.61(15) . . ?
O11 Mn1 N1 91.02(18) . . ?
O21 Mn1 N1 99.03(17) . . ?
O11 Mn1 N4 98.19(18) . . ?
O21 Mn1 N4 90.67(17) . . ?
N1 Mn1 N4 166.45(18) . . ?
O11 Mn1 N2 163.77(17) . . ?
O21 Mn1 N2 98.81(16) . . ?
N1 Mn1 N2 75.14(17) . . ?
N4 Mn1 N2 94.12(18) . . ?
O11 Mn1 N3 93.34(16) . . ?
O21 Mn1 N3 165.90(16) . . ?
N1 Mn1 N3 94.08(17) . . ?
N4 Mn1 N3 75.56(18) . . ?
N2 Mn1 N3 79.49(16) . . ?
C1 N1 C9 115.8(5) . . ?
C1 N1 Mn1 125.8(4) . . ?
C9 N1 Mn1 117.9(4) . . ?
C8 N2 C21 111.0(4) . . ?
C8 N2 C10 109.4(5) . . ?
C21 N2 C10 107.7(4) . . ?
C8 N2 Mn1 110.3(3) . . ?
C21 N2 Mn1 113.3(3) . . ?
C10 N2 Mn1 104.8(3) . . ?
C11 N3 C12 111.0(4) . . ?
C11 N3 C22 110.1(5) . . ?
C12 N3 C22 112.0(4) . . ?
C11 N3 Mn1 103.9(3) . . ?
C12 N3 Mn1 108.9(3) . . ?
C22 N3 Mn1 110.6(3) . . ?
C19 N4 C20 116.8(5) . . ?
C19 N4 Mn1 126.2(4) . . ?
C20 N4 Mn1 116.9(4) . . ?
N1 C1 C2 124.6(7) . . ?
N1 C1 H1 117.7 . . ?
C2 C1 H1 117.7 . . ?
C3 C2 C1 118.9(7) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 120.9(7) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C9 C4 C3 116.6(6) . . ?
C9 C4 C5 119.8(6) . . ?
C3 C4 C5 123.6(7) . . ?
C6 C5 C4 120.3(6) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 119.1(6) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C8 C7 C6 122.5(6) . . ?
C8 C7 H7 118.8 . . ?
C6 C7 H7 118.8 . . ?
C7 C8 C9 119.3(6) . . ?
C7 C8 N2 122.6(5) . . ?
C9 C8 N2 118.0(5) . . ?
N1 C9 C4 123.1(6) . . ?
N1 C9 C8 118.0(5) . . ?
C4 C9 C8 118.9(6) . . ?
N2 C10 C11 110.9(4) . . ?
N2 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.0 . . ?
N3 C11 C10 112.0(5) . . ?
N3 C11 H11A 109.2 . . ?
C10 C11 H11A 109.2 . . ?
N3 C11 H11B 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C20 119.5(6) . . ?
C13 C12 N3 121.6(6) . . ?
C20 C12 N3 118.8(5) . . ?
C14 C13 C12 120.2(7) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 122.3(7) . . ?
C15 C14 H14 118.9 . . ?
C13 C14 H14 118.9 . . ?
C14 C15 C16 119.5(7) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C20 C16 C17 118.7(6) . . ?
C20 C16 C15 118.9(6) . . ?
C17 C16 C15 122.4(6) . . ?
C18 C17 C16 118.5(6) . . ?
C18 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
C17 C18 C19 119.4(7) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
N4 C19 C18 125.4(6) . . ?
N4 C19 H19 117.3 . . ?
C18 C19 H19 117.3 . . ?
N4 C20 C16 121.2(5) . . ?
N4 C20 C12 119.2(5) . . ?
C16 C20 C12 119.5(6) . . ?
N2 C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N3 C22 H22A 109.5 . . ?
N3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O13 S1 O11 115.2(3) . . ?
O13 S1 O12 117.4(4) . . ?
O11 S1 O12 112.4(3) . . ?
O13 S1 C111 103.2(4) . . ?
O11 S1 C111 105.1(3) . . ?
O12 S1 C111 101.0(4) . . ?
S1 O11 Mn1 159.7(3) . . ?
F12 C111 F13 108.6(7) . . ?
F12 C111 F11 106.5(7) . . ?
F13 C111 F11 105.5(7) . . ?
F12 C111 S1 113.7(6) . . ?
F13 C111 S1 112.7(6) . . ?
F11 C111 S1 109.5(6) . . ?
O23 S2 O22 116.8(3) . . ?
O23 S2 O21 113.4(3) . . ?
O22 S2 O21 113.7(3) . . ?
O23 S2 C211 104.0(4) . . ?
O22 S2 C211 104.3(4) . . ?
O21 S2 C211 102.6(3) . . ?
S2 O21 Mn1 135.4(3) . . ?
F23 C211 F21 108.9(7) . . ?
F23 C211 F22 107.2(7) . . ?
F21 C211 F22 106.5(7) . . ?
F23 C211 S2 112.1(6) . . ?
F21 C211 S2 111.9(6) . . ?
F22 C211 S2 110.0(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
O11 Mn1 N1 C1 -9.6(5) . . . . ?
O21 Mn1 N1 C1 82.2(5) . . . . ?
N4 Mn1 N1 C1 -142.6(7) . . . . ?
N2 Mn1 N1 C1 179.0(5) . . . . ?
N3 Mn1 N1 C1 -103.0(5) . . . . ?
O11 Mn1 N1 C9 178.4(4) . . . . ?
O21 Mn1 N1 C9 -89.8(4) . . . . ?
N4 Mn1 N1 C9 45.4(10) . . . . ?
N2 Mn1 N1 C9 7.0(4) . . . . ?
N3 Mn1 N1 C9 85.0(4) . . . . ?
O11 Mn1 N2 C8 -38.6(7) . . . . ?
O21 Mn1 N2 C8 90.7(3) . . . . ?
N1 Mn1 N2 C8 -6.3(3) . . . . ?
N4 Mn1 N2 C8 -177.9(3) . . . . ?
N3 Mn1 N2 C8 -103.5(4) . . . . ?
O11 Mn1 N2 C21 -163.8(5) . . . . ?
O21 Mn1 N2 C21 -34.4(4) . . . . ?
N1 Mn1 N2 C21 -131.5(4) . . . . ?
N4 Mn1 N2 C21 56.9(4) . . . . ?
N3 Mn1 N2 C21 131.3(4) . . . . ?
O11 Mn1 N2 C10 79.0(7) . . . . ?
O21 Mn1 N2 C10 -151.6(4) . . . . ?
N1 Mn1 N2 C10 111.3(4) . . . . ?
N4 Mn1 N2 C10 -60.3(4) . . . . ?
N3 Mn1 N2 C10 14.2(4) . . . . ?
O11 Mn1 N3 C11 -149.3(3) . . . . ?
O21 Mn1 N3 C11 100.3(7) . . . . ?
N1 Mn1 N3 C11 -58.0(3) . . . . ?
N4 Mn1 N3 C11 113.1(3) . . . . ?
N2 Mn1 N3 C11 16.0(3) . . . . ?
O11 Mn1 N3 C12 92.3(3) . . . . ?
O21 Mn1 N3 C12 -18.1(9) . . . . ?
N1 Mn1 N3 C12 -176.4(3) . . . . ?
N4 Mn1 N3 C12 -5.3(3) . . . . ?
N2 Mn1 N3 C12 -102.4(3) . . . . ?
O11 Mn1 N3 C22 -31.2(4) . . . . ?
O21 Mn1 N3 C22 -141.6(6) . . . . ?
N1 Mn1 N3 C22 60.0(4) . . . . ?
N4 Mn1 N3 C22 -128.8(4) . . . . ?
N2 Mn1 N3 C22 134.1(4) . . . . ?
O11 Mn1 N4 C19 90.9(5) . . . . ?
O21 Mn1 N4 C19 -0.8(5) . . . . ?
N1 Mn1 N4 C19 -136.7(7) . . . . ?
N2 Mn1 N4 C19 -99.7(5) . . . . ?
N3 Mn1 N4 C19 -177.7(5) . . . . ?
O11 Mn1 N4 C20 -85.1(4) . . . . ?
O21 Mn1 N4 C20 -176.8(4) . . . . ?
N1 Mn1 N4 C20 47.3(10) . . . . ?
N2 Mn1 N4 C20 84.3(4) . . . . ?
N3 Mn1 N4 C20 6.3(4) . . . . ?
C9 N1 C1 C2 -3.3(9) . . . . ?
Mn1 N1 C1 C2 -175.5(5) . . . . ?
N1 C1 C2 C3 4.0(12) . . . . ?
C1 C2 C3 C4 -3.4(12) . . . . ?
C2 C3 C4 C9 2.4(10) . . . . ?
C2 C3 C4 C5 -178.4(7) . . . . ?
C9 C4 C5 C6 -0.4(9) . . . . ?
C3 C4 C5 C6 -179.7(6) . . . . ?
C4 C5 C6 C7 0.1(9) . . . . ?
C5 C6 C7 C8 0.2(9) . . . . ?
C6 C7 C8 C9 -0.3(9) . . . . ?
C6 C7 C8 N2 -179.0(5) . . . . ?
C21 N2 C8 C7 -49.3(7) . . . . ?
C10 N2 C8 C7 69.5(7) . . . . ?
Mn1 N2 C8 C7 -175.8(5) . . . . ?
C21 N2 C8 C9 132.0(5) . . . . ?
C10 N2 C8 C9 -109.2(6) . . . . ?
Mn1 N2 C8 C9 5.6(6) . . . . ?
C1 N1 C9 C4 2.2(9) . . . . ?
Mn1 N1 C9 C4 175.0(4) . . . . ?
C1 N1 C9 C8 -179.2(5) . . . . ?
Mn1 N1 C9 C8 -6.4(7) . . . . ?
C3 C4 C9 N1 -1.8(9) . . . . ?
C5 C4 C9 N1 178.9(6) . . . . ?
C3 C4 C9 C8 179.6(6) . . . . ?
C5 C4 C9 C8 0.3(9) . . . . ?
C7 C8 C9 N1 -178.6(6) . . . . ?
N2 C8 C9 N1 0.1(8) . . . . ?
C7 C8 C9 C4 0.0(9) . . . . ?
N2 C8 C9 C4 178.7(5) . . . . ?
C8 N2 C10 C11 75.4(6) . . . . ?
C21 N2 C10 C11 -163.8(5) . . . . ?
Mn1 N2 C10 C11 -42.8(5) . . . . ?
C12 N3 C11 C10 71.8(6) . . . . ?
C22 N3 C11 C10 -163.6(5) . . . . ?
Mn1 N3 C11 C10 -45.2(5) . . . . ?
N2 C10 C11 N3 64.2(6) . . . . ?
C11 N3 C12 C13 72.1(7) . . . . ?
C22 N3 C12 C13 -51.4(7) . . . . ?
Mn1 N3 C12 C13 -174.1(5) . . . . ?
C11 N3 C12 C20 -109.6(6) . . . . ?
C22 N3 C12 C20 126.9(5) . . . . ?
Mn1 N3 C12 C20 4.2(6) . . . . ?
C20 C12 C13 C14 3.3(9) . . . . ?
N3 C12 C13 C14 -178.4(5) . . . . ?
C12 C13 C14 C15 -2.1(10) . . . . ?
C13 C14 C15 C16 0.4(10) . . . . ?
C14 C15 C16 C20 0.0(9) . . . . ?
C14 C15 C16 C17 179.5(6) . . . . ?
C20 C16 C17 C18 1.0(9) . . . . ?
C15 C16 C17 C18 -178.4(6) . . . . ?
C16 C17 C18 C19 -0.7(10) . . . . ?
C20 N4 C19 C18 0.9(10) . . . . ?
Mn1 N4 C19 C18 -175.2(5) . . . . ?
C17 C18 C19 N4 -0.3(11) . . . . ?
C19 N4 C20 C16 -0.5(9) . . . . ?
Mn1 N4 C20 C16 175.9(4) . . . . ?
C19 N4 C20 C12 177.3(5) . . . . ?
Mn1 N4 C20 C12 -6.3(7) . . . . ?
C17 C16 C20 N4 -0.5(9) . . . . ?
C15 C16 C20 N4 179.0(5) . . . . ?
C17 C16 C20 C12 -178.3(6) . . . . ?
C15 C16 C20 C12 1.2(9) . . . . ?
C13 C12 C20 N4 179.3(6) . . . . ?
N3 C12 C20 N4 0.9(8) . . . . ?
C13 C12 C20 C16 -2.9(9) . . . . ?
N3 C12 C20 C16 178.8(5) . . . . ?
O13 S1 O11 Mn1 46.8(9) . . . . ?
O12 S1 O11 Mn1 -175.0(7) . . . . ?
C111 S1 O11 Mn1 -66.1(9) . . . . ?
O21 Mn1 O11 S1 89.2(8) . . . . ?
N1 Mn1 O11 S1 -171.7(8) . . . . ?
N4 Mn1 O11 S1 -1.7(8) . . . . ?
N2 Mn1 O11 S1 -140.6(7) . . . . ?
N3 Mn1 O11 S1 -77.6(8) . . . . ?
O13 S1 C111 F12 57.1(8) . . . . ?
O11 S1 C111 F12 178.2(6) . . . . ?
O12 S1 C111 F12 -64.8(8) . . . . ?
O13 S1 C111 F13 -178.8(7) . . . . ?
O11 S1 C111 F13 -57.8(7) . . . . ?
O12 S1 C111 F13 59.3(7) . . . . ?
O13 S1 C111 F11 -61.8(6) . . . . ?
O11 S1 C111 F11 59.2(6) . . . . ?
O12 S1 C111 F11 176.3(6) . . . . ?
O23 S2 O21 Mn1 141.1(3) . . . . ?
O22 S2 O21 Mn1 4.6(5) . . . . ?
C211 S2 O21 Mn1 -107.4(4) . . . . ?
O11 Mn1 O21 S2 118.0(4) . . . . ?
N1 Mn1 O21 S2 26.7(4) . . . . ?
N4 Mn1 O21 S2 -143.8(4) . . . . ?
N2 Mn1 O21 S2 -49.5(4) . . . . ?
N3 Mn1 O21 S2 -131.4(6) . . . . ?
O23 S2 C211 F23 173.4(5) . . . . ?
O22 S2 C211 F23 -63.7(6) . . . . ?
O21 S2 C211 F23 55.0(7) . . . . ?
O23 S2 C211 F21 50.8(6) . . . . ?
O22 S2 C211 F21 173.6(5) . . . . ?
O21 S2 C211 F21 -67.6(6) . . . . ?
O23 S2 C211 F22 -67.4(7) . . . . ?
O22 S2 C211 F22 55.4(7) . . . . ?
O21 S2 C211 F22 174.2(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.616
_refine_diff_density_min         -0.705
_refine_diff_density_rms         0.123