# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_OMe-Mn-CO

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H14 Br Mn N2 O4 S'
_chemical_formula_sum            'C17 H14 Br Mn N2 O4 S'
_chemical_formula_weight         477.21

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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5300(3)
_cell_length_b                   7.6723(3)
_cell_length_c                   17.7327(6)
_cell_angle_alpha                87.250(2)
_cell_angle_beta                 79.371(2)
_cell_angle_gamma                66.350(2)
_cell_volume                     921.93(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    163(2)
_cell_measurement_reflns_used    9956
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      27.51

_exptl_crystal_description       Block
_exptl_crystal_colour            Orange
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      1.719
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             476
_exptl_absorpt_coefficient_mu    3.021
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4093
_exptl_absorpt_correction_T_max  0.7727
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      163(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            33162
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0202
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.17
_diffrn_reflns_theta_max         27.49
_reflns_number_total             4223
_reflns_number_gt                3887
_reflns_threshold_expression     >2sigma(I)

_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          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0370P)²+0.5339P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4223
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0232
_refine_ls_wR_factor_ref         0.0700
_refine_ls_wR_factor_gt          0.0676
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2758(3) 0.3268(3) 0.01277(11) 0.0226(4) Uani 1 1 d . . .
H1A H 0.3510 0.3587 -0.0330 0.034 Uiso 1 1 calc R . .
H1B H 0.1393 0.3643 0.0059 0.034 Uiso 1 1 calc R . .
H1C H 0.3352 0.1893 0.0204 0.034 Uiso 1 1 calc R . .
C2 C 0.4521(3) 0.3864(3) 0.09965(10) 0.0163(3) Uani 1 1 d . . .
C3 C 0.6317(3) 0.2514(3) 0.06130(11) 0.0219(4) Uani 1 1 d . . .
H3 H 0.6363 0.1836 0.0171 0.026 Uiso 1 1 calc R . .
C4 C 0.8011(3) 0.2191(3) 0.08888(12) 0.0257(4) Uani 1 1 d . . .
H4 H 0.9242 0.1287 0.0635 0.031 Uiso 1 1 calc R . .
C5 C 0.7918(3) 0.3186(3) 0.15373(12) 0.0241(4) Uani 1 1 d . . .
H5 H 0.9068 0.2964 0.1742 0.029 Uiso 1 1 calc R . .
C6 C 0.6103(3) 0.4510(3) 0.18753(10) 0.0183(4) Uani 1 1 d . . .
C7 C 0.5838(3) 0.5671(3) 0.25441(11) 0.0197(4) Uani 1 1 d . . .
H7 H 0.6929 0.5567 0.2767 0.024 Uiso 1 1 calc R . .
C8 C 0.3851(3) 0.8160(3) 0.34208(11) 0.0186(4) Uani 1 1 d . . .
C9 C 0.4493(3) 0.9616(3) 0.32240(12) 0.0258(4) Uani 1 1 d . . .
H9 H 0.5139 0.9672 0.2716 0.031 Uiso 1 1 calc R . .
C10 C 0.4182(3) 1.0990(3) 0.37758(14) 0.0320(5) Uani 1 1 d . . .
H10 H 0.4604 1.1997 0.3647 0.038 Uiso 1 1 calc R . .
C11 C 0.3254(3) 1.0870(3) 0.45117(14) 0.0316(5) Uani 1 1 d . . .
H11 H 0.3022 1.1814 0.4888 0.038 Uiso 1 1 calc R . .
C12 C 0.2656(3) 0.9404(3) 0.47109(12) 0.0273(4) Uani 1 1 d . . .
H12 H 0.2039 0.9339 0.5223 0.033 Uiso 1 1 calc R . .
C13 C 0.2946(3) 0.8019(3) 0.41684(11) 0.0209(4) Uani 1 1 d . . .
C14 C 0.1926(4) 0.6031(4) 0.54053(12) 0.0358(5) Uani 1 1 d . . .
H14A H 0.3134 0.5931 0.5571 0.054 Uiso 1 1 calc R . .
H14B H 0.1626 0.4933 0.5583 0.054 Uiso 1 1 calc R . .
H14C H 0.0831 0.7205 0.5623 0.054 Uiso 1 1 calc R . .
C15 C 0.0073(3) 0.9034(3) 0.28130(11) 0.0232(4) Uani 1 1 d . . .
C16 C 0.0202(3) 0.7391(3) 0.15866(11) 0.0212(4) Uani 1 1 d . . .
C17 C 0.1099(3) 0.5371(3) 0.27209(11) 0.0224(4) Uani 1 1 d . . .
N1 N 0.4402(2) 0.4880(2) 0.16112(8) 0.0153(3) Uani 1 1 d . . .
N2 N 0.4092(2) 0.6837(2) 0.28219(8) 0.0169(3) Uani 1 1 d . . .
O1 O 0.2789(2) 0.4267(2) 0.07881(8) 0.0219(3) Uani 1 1 d . . .
O2 O -0.1114(2) 1.0286(3) 0.31793(10) 0.0376(4) Uani 1 1 d . . .
O3 O -0.0980(2) 0.7663(2) 0.12237(10) 0.0344(4) Uani 1 1 d . . .
O4 O 0.0490(2) 0.4314(2) 0.29837(9) 0.0330(4) Uani 1 1 d . . .
S1 S 0.22675(9) 0.60753(8) 0.43741(3) 0.02881(13) Uani 1 1 d . . .
Br1 Br 0.29994(3) 0.94109(3) 0.142109(10) 0.02166(7) Uani 1 1 d . . .
Mn Mn 0.19448(4) 0.70652(4) 0.221886(15) 0.01498(8) 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
C1 O1 1.439(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O1 1.333(2) . ?
C2 N1 1.340(2) . ?
C2 C3 1.403(3) . ?
C3 C4 1.375(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.378(3) . ?
C5 H5 0.9500 . ?
C6 N1 1.363(2) . ?
C6 C7 1.453(3) . ?
C7 N2 1.277(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.391(3) . ?
C8 C13 1.395(3) . ?
C8 N2 1.441(2) . ?
C9 C10 1.393(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.392(3) . ?
C12 H12 0.9500 . ?
C13 S1 1.763(2) . ?
C14 S1 1.800(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 O2 1.140(3) . ?
C15 Mn 1.810(2) . ?
C16 O3 1.140(2) . ?
C16 Mn 1.815(2) . ?
C17 O4 1.126(3) . ?
C17 Mn 1.798(2) . ?
N1 Mn 2.0844(15) . ?
N2 Mn 2.0446(15) . ?
Br1 Mn 2.5216(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 N1 113.71(16) . . ?
O1 C2 C3 123.95(17) . . ?
N1 C2 C3 122.34(17) . . ?
C4 C3 C2 118.85(18) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 119.86(18) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 117.88(18) . . ?
C6 C5 H5 121.1 . . ?
C4 C5 H5 121.1 . . ?
N1 C6 C5 123.70(18) . . ?
N1 C6 C7 113.63(16) . . ?
C5 C6 C7 122.66(18) . . ?
N2 C7 C6 117.88(17) . . ?
N2 C7 H7 121.1 . . ?
C6 C7 H7 121.1 . . ?
C9 C8 C13 121.19(18) . . ?
C9 C8 N2 117.89(17) . . ?
C13 C8 N2 120.89(17) . . ?
C8 C9 C10 119.7(2) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 119.1(2) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C12 C11 C10 121.2(2) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 120.7(2) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C8 118.15(19) . . ?
C12 C13 S1 123.80(16) . . ?
C8 C13 S1 118.05(15) . . ?
S1 C14 H14A 109.5 . . ?
S1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
S1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C15 Mn 179.1(2) . . ?
O3 C16 Mn 175.87(18) . . ?
O4 C17 Mn 174.03(18) . . ?
C2 N1 C6 117.32(16) . . ?
C2 N1 Mn 128.71(12) . . ?
C6 N1 Mn 113.93(12) . . ?
C7 N2 C8 117.99(16) . . ?
C7 N2 Mn 116.24(13) . . ?
C8 N2 Mn 124.30(12) . . ?
C2 O1 C1 118.09(15) . . ?
C13 S1 C14 102.54(11) . . ?
C17 Mn C15 92.38(9) . . ?
C17 Mn C16 87.71(9) . . ?
C15 Mn C16 88.65(9) . . ?
C17 Mn N2 99.11(8) . . ?
C15 Mn N2 93.61(8) . . ?
C16 Mn N2 172.70(8) . . ?
C17 Mn N1 91.06(8) . . ?
C15 Mn N1 171.39(8) . . ?
C16 Mn N1 99.38(7) . . ?
N2 Mn N1 78.04(6) . . ?
C17 Mn Br1 175.11(6) . . ?
C15 Mn Br1 88.96(7) . . ?
C16 Mn Br1 87.62(7) . . ?
N2 Mn Br1 85.49(4) . . ?
N1 Mn Br1 88.26(4) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.667
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.081
_database_code_depnum_ccdc_archive 'CCDC 988783'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Me-MnCO

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 Br Cl2 Mn N2 O3 S'
_chemical_formula_sum            'C18 H16 Br Cl2 Mn N2 O3 S'
_chemical_formula_weight         546.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7613(3)
_cell_length_b                   10.8921(4)
_cell_length_c                   13.0888(5)
_cell_angle_alpha                66.319(2)
_cell_angle_beta                 79.790(2)
_cell_angle_gamma                69.483(2)
_cell_volume                     1070.35(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    163(2)
_cell_measurement_reflns_used    9895
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      27.88

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    2.852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2598
_exptl_absorpt_correction_T_max  0.7369
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      163(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            39161
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4903
_reflns_number_gt                4419
_reflns_threshold_expression     >2sigma(I)

_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          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0264P)²+3.6398P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4903
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0842
_refine_ls_wR_factor_gt          0.0792
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4125(4) 0.6408(4) 0.3244(3) 0.0284(7) Uani 1 1 d . . .
H1A H 0.3186 0.7213 0.2894 0.043 Uiso 1 1 calc R . .
H1B H 0.4954 0.6750 0.3356 0.043 Uiso 1 1 calc R . .
H1C H 0.3773 0.5806 0.3967 0.043 Uiso 1 1 calc R . .
C2 C 0.4828(3) 0.5578(3) 0.2503(2) 0.0171(5) Uani 1 1 d . . .
C3 C 0.6294(3) 0.5677(3) 0.1896(3) 0.0212(6) Uani 1 1 d . . .
H3 H 0.6819 0.6272 0.1958 0.025 Uiso 1 1 calc R . .
C4 C 0.6986(4) 0.4923(3) 0.1211(3) 0.0241(6) Uani 1 1 d . . .
H4 H 0.7967 0.5009 0.0786 0.029 Uiso 1 1 calc R . .
C5 C 0.6217(3) 0.4034(3) 0.1155(2) 0.0203(6) Uani 1 1 d . . .
H5 H 0.6665 0.3489 0.0698 0.024 Uiso 1 1 calc R . .
C6 C 0.4782(3) 0.3963(3) 0.1781(2) 0.0145(5) Uani 1 1 d . . .
C7 C 0.3982(3) 0.2981(3) 0.1830(2) 0.0156(5) Uani 1 1 d . . .
H7 H 0.4371 0.2426 0.1378 0.019 Uiso 1 1 calc R . .
C8 C 0.1910(3) 0.1939(3) 0.2517(2) 0.0142(5) Uani 1 1 d . . .
C9 C 0.1067(4) 0.2265(3) 0.1595(2) 0.0197(6) Uani 1 1 d . . .
H9 H 0.1071 0.3083 0.0951 0.024 Uiso 1 1 calc R . .
C10 C 0.0212(4) 0.1392(3) 0.1610(3) 0.0243(6) Uani 1 1 d . . .
H10 H -0.0372 0.1613 0.0981 0.029 Uiso 1 1 calc R . .
C11 C 0.0226(4) 0.0201(3) 0.2551(3) 0.0235(6) Uani 1 1 d . . .
H11 H -0.0365 -0.0391 0.2568 0.028 Uiso 1 1 calc R . .
C12 C 0.1087(4) -0.0142(3) 0.3470(3) 0.0215(6) Uani 1 1 d . . .
H12 H 0.1095 -0.0972 0.4105 0.026 Uiso 1 1 calc R . .
C13 C 0.1943(3) 0.0724(3) 0.3471(2) 0.0167(5) Uani 1 1 d . . .
C14 C 0.3087(4) -0.1343(3) 0.5512(3) 0.0271(7) Uani 1 1 d . . .
H14A H 0.1971 -0.1308 0.5809 0.041 Uiso 1 1 calc R . .
H14B H 0.3799 -0.1666 0.6128 0.041 Uiso 1 1 calc R . .
H14C H 0.3477 -0.1998 0.5114 0.041 Uiso 1 1 calc R . .
C15 C -0.0060(3) 0.3993(3) 0.3667(2) 0.0169(5) Uani 1 1 d . . .
C16 C 0.2663(3) 0.3509(3) 0.4506(2) 0.0173(5) Uani 1 1 d . . .
C17 C 0.0843(3) 0.6009(3) 0.3468(2) 0.0170(5) Uani 1 1 d . . .
C18 C 0.2704(6) 1.0553(4) -0.0610(4) 0.0553(12) Uani 1 1 d . . .
H18A H 0.3183 1.0899 -0.0190 0.066 Uiso 1 1 calc R . .
H18B H 0.1570 1.1179 -0.0771 0.066 Uiso 1 1 calc R . .
N1 N 0.4055(3) 0.4738(2) 0.24323(18) 0.0129(4) Uani 1 1 d . . .
N2 N 0.2735(3) 0.2882(2) 0.24980(18) 0.0135(4) Uani 1 1 d . . .
O1 O -0.1254(3) 0.3744(3) 0.40080(19) 0.0298(5) Uani 1 1 d . . .
O2 O 0.3204(3) 0.3026(3) 0.53659(18) 0.0283(5) Uani 1 1 d . . .
O3 O 0.0140(3) 0.6982(2) 0.3680(2) 0.0282(5) Uani 1 1 d . . .
S1 S 0.31141(11) 0.03813(8) 0.45674(7) 0.0310(2) Uani 1 1 d . . .
Mn1 Mn 0.18119(5) 0.44359(4) 0.31439(3) 0.01127(9) Uani 1 1 d . . .
Br1 Br 0.06291(3) 0.59853(3) 0.12468(2) 0.01596(8) Uani 1 1 d . . .
Cl1 Cl 0.2679(2) 0.88405(11) 0.02120(9) 0.0634(4) Uani 1 1 d . . .
Cl2 Cl 0.3825(2) 1.06391(14) -0.18669(14) 0.0925(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
C1 C2 1.496(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 N1 1.352(3) . ?
C2 C3 1.400(4) . ?
C3 C4 1.376(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(4) . ?
C5 H5 0.9500 . ?
C6 N1 1.361(4) . ?
C6 C7 1.447(4) . ?
C7 N2 1.280(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(4) . ?
C8 C13 1.403(4) . ?
C8 N2 1.439(3) . ?
C9 C10 1.394(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.396(4) . ?
C12 H12 0.9500 . ?
C13 S1 1.753(3) . ?
C14 S1 1.792(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 O1 1.142(4) . ?
C15 Mn1 1.811(3) . ?
C16 O2 1.143(3) . ?
C16 Mn1 1.803(3) . ?
C17 O3 1.139(4) . ?
C17 Mn1 1.809(3) . ?
C18 Cl1 1.745(4) . ?
C18 Cl2 1.746(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
N1 Mn1 2.097(2) . ?
N2 Mn1 2.045(2) . ?
Mn1 Br1 2.5314(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 120.8(3) . . ?
N1 C2 C1 120.1(2) . . ?
C3 C2 C1 119.1(3) . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 118.5(3) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C6 C5 C4 118.3(3) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
N1 C6 C5 123.8(3) . . ?
N1 C6 C7 114.9(2) . . ?
C5 C6 C7 121.2(3) . . ?
N2 C7 C6 118.2(2) . . ?
N2 C7 H7 120.9 . . ?
C6 C7 H7 120.9 . . ?
C9 C8 C13 121.0(2) . . ?
C9 C8 N2 119.1(2) . . ?
C13 C8 N2 119.9(2) . . ?
C8 C9 C10 120.0(3) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 119.3(3) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C12 121.0(3) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C11 C12 C13 120.5(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C8 118.2(2) . . ?
C12 C13 S1 124.7(2) . . ?
C8 C13 S1 117.1(2) . . ?
S1 C14 H14A 109.5 . . ?
S1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
S1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 C15 Mn1 178.0(3) . . ?
O2 C16 Mn1 174.4(3) . . ?
O3 C17 Mn1 175.6(2) . . ?
Cl1 C18 Cl2 112.0(2) . . ?
Cl1 C18 H18A 109.2 . . ?
Cl2 C18 H18A 109.2 . . ?
Cl1 C18 H18B 109.2 . . ?
Cl2 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C2 N1 C6 117.6(2) . . ?
C2 N1 Mn1 130.57(19) . . ?
C6 N1 Mn1 111.78(17) . . ?
C7 N2 C8 118.0(2) . . ?
C7 N2 Mn1 114.60(18) . . ?
C8 N2 Mn1 125.62(17) . . ?
C13 S1 C14 103.40(14) . . ?
C16 Mn1 C17 90.25(13) . . ?
C16 Mn1 C15 91.96(12) . . ?
C17 Mn1 C15 86.91(12) . . ?
C16 Mn1 N2 100.16(11) . . ?
C17 Mn1 N2 169.58(11) . . ?
C15 Mn1 N2 93.24(11) . . ?
C16 Mn1 N1 90.39(10) . . ?
C17 Mn1 N1 100.84(10) . . ?
C15 Mn1 N1 171.89(11) . . ?
N2 Mn1 N1 78.71(9) . . ?
C16 Mn1 Br1 173.59(9) . . ?
C17 Mn1 Br1 84.14(9) . . ?
C15 Mn1 Br1 90.85(9) . . ?
N2 Mn1 Br1 85.43(6) . . ?
N1 Mn1 Br1 87.62(6) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         2.097
_refine_diff_density_min         -1.790
_refine_diff_density_rms         0.097
_database_code_depnum_ccdc_archive 'CCDC 988784'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Me-Br2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 Br2 Mn N2 S'
_chemical_formula_sum            'C14 H14 Br2 Mn N2 S'
_chemical_formula_weight         457.09

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'
Br Br -0.2901 2.4595 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_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                   11.838(3)
_cell_length_b                   10.124(3)
_cell_length_c                   13.654(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.610(7)
_cell_angle_gamma                90.00
_cell_volume                     1596.9(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2709
_cell_measurement_theta_min      1.9815
_cell_measurement_theta_max      30.4947

_exptl_crystal_description       Prism
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.297
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.092
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.901
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             892
_exptl_absorpt_coefficient_mu    5.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5169
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(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  'Rigaku SCX-Mini with Mercury 2 CCD'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13328
_diffrn_reflns_av_R_equivalents  0.2481
_diffrn_reflns_av_sigmaI/netI    0.1891
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2808
_reflns_number_gt                1876
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² 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/[σ²(Fo²)+(0.0973P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2808
_refine_ls_number_parameters     183
_refine_ls_number_restraints     120
_refine_ls_R_factor_all          0.1217
_refine_ls_R_factor_gt           0.0872
_refine_ls_wR_factor_ref         0.2242
_refine_ls_wR_factor_gt          0.2012
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.989
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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
C1 C 0.6968(9) 0.4615(9) 0.1591(8) 0.040(3) Uani 1 1 d U . .
H1A H 0.6303 0.4252 0.1110 0.061 Uiso 1 1 calc R . .
H1B H 0.6707 0.4989 0.2166 0.061 Uiso 1 1 calc R . .
H1C H 0.7531 0.3911 0.1822 0.061 Uiso 1 1 calc R . .
C2 C 0.7512(8) 0.5655(9) 0.1103(7) 0.031(2) Uani 1 1 d U . .
C3 C 0.7546(9) 0.6994(9) 0.1428(8) 0.040(3) Uani 1 1 d U . .
H3 H 0.7191 0.7242 0.1961 0.048 Uiso 1 1 calc R . .
C4 C 0.8100(9) 0.7933(9) 0.0962(8) 0.039(3) Uani 1 1 d U . .
H4 H 0.8168 0.8821 0.1192 0.047 Uiso 1 1 calc R . .
C5 C 0.8550(9) 0.7544(9) 0.0156(7) 0.037(3) Uani 1 1 d U . .
H5 H 0.8915 0.8171 -0.0190 0.044 Uiso 1 1 calc R . .
C6 C 0.8469(8) 0.6254(9) -0.0140(7) 0.027(2) Uani 1 1 d U . .
C7 C 0.8917(8) 0.5836(9) -0.0998(7) 0.032(2) Uani 1 1 d U . .
H7 H 0.9295 0.6460 -0.1336 0.038 Uiso 1 1 calc R . .
C8 C 0.9232(8) 0.4245(9) -0.2161(7) 0.029(2) Uani 1 1 d U . .
C9 C 0.9876(9) 0.5087(10) -0.2660(8) 0.042(3) Uani 1 1 d U . .
H9 H 1.0042 0.5967 -0.2431 0.051 Uiso 1 1 calc R . .
C10 C 1.0260(10) 0.4626(11) -0.3476(8) 0.049(3) Uani 1 1 d U . .
H10 H 1.0712 0.5191 -0.3793 0.059 Uiso 1 1 calc R . .
C11 C 1.0010(10) 0.3376(10) -0.3845(9) 0.049(3) Uani 1 1 d U . .
H11 H 1.0290 0.3077 -0.4408 0.059 Uiso 1 1 calc R . .
C12 C 0.9346(9) 0.2555(10) -0.3392(8) 0.039(3) Uani 1 1 d U . .
H12 H 0.9151 0.1697 -0.3657 0.047 Uiso 1 1 calc R . .
C13 C 0.8961(8) 0.2970(9) -0.2551(7) 0.031(2) Uani 1 1 d U . .
C14 C 0.8819(10) 0.0491(9) -0.1699(9) 0.052(3) Uani 1 1 d U . .
H14A H 0.9061 0.0122 -0.2285 0.078 Uiso 1 1 calc R . .
H14B H 0.8342 -0.0156 -0.1440 0.078 Uiso 1 1 calc R . .
H14C H 0.9505 0.0701 -0.1177 0.078 Uiso 1 1 calc R . .
Br1 Br 0.86417(9) 0.17343(9) 0.08341(8) 0.0379(4) Uani 1 1 d U . .
Br2 Br 0.56517(9) 0.34515(10) -0.10926(8) 0.0415(4) Uani 1 1 d U . .
Mn1 Mn 0.77807(13) 0.33709(13) -0.04762(11) 0.0280(4) Uani 1 1 d U . .
N1 N 0.7972(7) 0.5330(7) 0.0315(6) 0.0324(19) Uani 1 1 d U . .
N2 N 0.8811(6) 0.4648(7) -0.1304(6) 0.0277(18) Uani 1 1 d U . .
S1 S 0.7995(2) 0.1965(2) -0.2058(2) 0.0369(7) Uani 1 1 d U . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.467(12) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 N1 1.348(11) . ?
C2 C3 1.424(12) . ?
C3 C4 1.385(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(14) . ?
C4 H4 0.9500 . ?
C5 C6 1.364(12) . ?
C5 H5 0.9500 . ?
C6 N1 1.329(11) . ?
C6 C7 1.450(13) . ?
C7 N2 1.271(11) . ?
C7 H7 0.9500 . ?
C8 C13 1.406(12) . ?
C8 C9 1.414(13) . ?
C8 N2 1.428(11) . ?
C9 C10 1.374(14) . ?
C9 H9 0.9500 . ?
C10 C11 1.371(14) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(15) . ?
C11 H11 0.9500 . ?
C12 C13 1.390(13) . ?
C12 H12 0.9500 . ?
C13 S1 1.769(10) . ?
C14 S1 1.792(10) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
Br1 Mn1 2.4877(18) . ?
Br2 Mn1 2.4781(19) . ?
Mn1 N2 2.245(8) . ?
Mn1 N1 2.246(8) . ?
Mn1 S1 2.645(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 119.4(9) . . ?
N1 C2 C1 118.7(8) . . ?
C3 C2 C1 121.8(9) . . ?
C4 C3 C2 119.6(9) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 118.3(9) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C6 C5 C4 119.6(9) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
N1 C6 C5 123.0(9) . . ?
N1 C6 C7 116.7(8) . . ?
C5 C6 C7 120.3(9) . . ?
N2 C7 C6 121.0(9) . . ?
N2 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C13 C8 C9 118.2(9) . . ?
C13 C8 N2 118.8(8) . . ?
C9 C8 N2 122.9(8) . . ?
C10 C9 C8 119.7(10) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C11 C10 C9 121.9(11) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C12 119.3(11) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C11 C12 C13 120.7(9) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C8 120.1(9) . . ?
C12 C13 S1 119.8(7) . . ?
C8 C13 S1 119.8(7) . . ?
S1 C14 H14A 109.5 . . ?
S1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
S1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 Mn1 N1 74.0(3) . . ?
N2 Mn1 Br2 115.72(19) . . ?
N1 Mn1 Br2 97.0(2) . . ?
N2 Mn1 Br1 124.30(19) . . ?
N1 Mn1 Br1 105.1(2) . . ?
Br2 Mn1 Br1 119.53(7) . . ?
N2 Mn1 S1 74.9(2) . . ?
N1 Mn1 S1 148.3(2) . . ?
Br2 Mn1 S1 90.70(8) . . ?
Br1 Mn1 S1 97.57(8) . . ?
C6 N1 C2 119.9(8) . . ?
C6 N1 Mn1 113.9(6) . . ?
C2 N1 Mn1 125.7(6) . . ?
C7 N2 C8 120.9(8) . . ?
C7 N2 Mn1 113.9(6) . . ?
C8 N2 Mn1 125.0(6) . . ?
C13 S1 C14 103.0(5) . . ?
C13 S1 Mn1 100.7(3) . . ?
C14 S1 Mn1 111.6(4) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.741
_refine_diff_density_min         -2.045
_refine_diff_density_rms         0.246
_database_code_depnum_ccdc_archive 'CCDC 988785'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_SB-Me_Mn-CO

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 Br Mn N2 O2 S'
_chemical_formula_sum            'C16 H14 Br Mn N2 O2 S'
_chemical_formula_weight         433.20

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   ' P 21/n '
_symmetry_space_group_name_Hall  ' -P 2yn '

loop_
_symmetry_equiv_pos_as_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                   8.7752(19)
_cell_length_b                   12.659(3)
_cell_length_c                   14.644(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.798(5)
_cell_angle_gamma                90.00
_cell_volume                     1624.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    4391
_cell_measurement_theta_min      2.1251
_cell_measurement_theta_max      27.4891

_exptl_crystal_description       Block
_exptl_crystal_colour            Orange
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.771
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    3.409
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4596
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
Abscor. T. Higashi (2001). The Rigaku Corporation, Tokyo, Japan.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      153(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  'Rigaku SCX-Mini with Mercury 2 CCD'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16808
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.10
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3713
_reflns_number_gt                3328
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² 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/[σ²(Fo²)+(0.0297P)²+1.3861P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3713
_refine_ls_number_parameters     210
_refine_ls_number_restraints     138
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0759
_refine_ls_wR_factor_gt          0.0735
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001

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
C1 C 0.8967(3) -0.00800(19) 0.16821(16) 0.0211(5) Uani 1 1 d U . .
H1 H 0.9330 0.0114 0.2266 0.025 Uiso 1 1 calc R . .
C2 C 0.9036(3) -0.1131(2) 0.14387(18) 0.0253(5) Uani 1 1 d U . .
H2 H 0.9449 -0.1629 0.1846 0.030 Uiso 1 1 calc R . .
C3 C 0.8479(3) -0.1430(2) 0.05763(17) 0.0259(5) Uani 1 1 d U . .
H3 H 0.8502 -0.2135 0.0397 0.031 Uiso 1 1 calc R . .
C4 C 0.7884(3) -0.0663(2) -0.00160(17) 0.0227(5) Uani 1 1 d U . .
H4 H 0.7498 -0.0848 -0.0597 0.027 Uiso 1 1 calc R . .
C5 C 0.7872(3) 0.03807(19) 0.02653(15) 0.0178(5) Uani 1 1 d U . .
C6 C 0.7362(3) 0.12660(19) -0.03205(16) 0.0186(5) Uani 1 1 d U . .
C7 C 0.6491(3) 0.1034(2) -0.12065(17) 0.0276(6) Uani 1 1 d U . .
H7A H 0.5841 0.1622 -0.1369 0.041 Uiso 1 1 calc R . .
H7B H 0.5880 0.0413 -0.1138 0.041 Uiso 1 1 calc R . .
H7C H 0.7194 0.0919 -0.1678 0.041 Uiso 1 1 calc R . .
C8 C 0.7426(3) 0.31573(18) -0.04517(16) 0.0183(5) Uani 1 1 d U . .
C9 C 0.7505(3) 0.3280(2) -0.13988(17) 0.0226(5) Uani 1 1 d U . .
H9 H 0.7759 0.2707 -0.1758 0.027 Uiso 1 1 calc R . .
C10 C 0.7207(3) 0.4250(2) -0.17996(17) 0.0258(5) Uani 1 1 d U . .
H10 H 0.7263 0.4324 -0.2429 0.031 Uiso 1 1 calc R . .
C11 C 0.6825(3) 0.5115(2) -0.12754(18) 0.0253(5) Uani 1 1 d U . .
H11 H 0.6562 0.5754 -0.1556 0.030 Uiso 1 1 calc R . .
C12 C 0.6837(3) 0.5022(2) -0.03314(18) 0.0239(5) Uani 1 1 d U . .
H12 H 0.6617 0.5604 0.0027 0.029 Uiso 1 1 calc R . .
C13 C 0.7180(3) 0.40514(19) 0.00768(16) 0.0192(5) Uani 1 1 d U . .
C14 C 0.8939(3) 0.4847(2) 0.1517(2) 0.0305(6) Uani 1 1 d U . .
H14A H 0.9782 0.4646 0.1162 0.046 Uiso 1 1 calc R . .
H14B H 0.9246 0.4828 0.2155 0.046 Uiso 1 1 calc R . .
H14C H 0.8619 0.5550 0.1352 0.046 Uiso 1 1 calc R . .
C15 C 0.8377(3) 0.20909(19) 0.26101(17) 0.0206(5) Uani 1 1 d U . .
C16 C 1.0135(3) 0.24970(19) 0.13939(16) 0.0197(5) Uani 1 1 d U . .
Mn1 Mn 0.81404(4) 0.22018(3) 0.13936(2) 0.01609(9) Uani 1 1 d U . .
N1 N 0.8404(2) 0.06774(16) 0.11193(13) 0.0176(4) Uani 1 1 d U . .
N2 N 0.7684(2) 0.21894(15) 0.00219(13) 0.0169(4) Uani 1 1 d U . .
O1 O 0.8578(2) 0.19731(15) 0.33887(12) 0.0296(4) Uani 1 1 d U . .
O2 O 1.1396(2) 0.26837(16) 0.14532(14) 0.0312(4) Uani 1 1 d U . .
S1 S 0.73648(7) 0.39354(5) 0.12950(4) 0.01976(13) Uani 1 1 d U . .
Br1 Br 0.52900(3) 0.18580(2) 0.153027(17) 0.02422(8) Uani 1 1 d U . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.343(3) . ?
C1 C2 1.379(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.385(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9300 . ?
C5 N1 1.366(3) . ?
C5 C6 1.468(3) . ?
C6 N2 1.298(3) . ?
C6 C7 1.502(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C13 1.394(3) . ?
C8 C9 1.401(3) . ?
C8 N2 1.421(3) . ?
C9 C10 1.380(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.389(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.393(3) . ?
C12 H12 0.9300 . ?
C13 S1 1.789(2) . ?
C14 S1 1.817(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 O1 1.155(3) . ?
C15 Mn1 1.789(3) . ?
C16 O2 1.131(3) . ?
C16 Mn1 1.789(3) . ?
Mn1 N1 1.987(2) . ?
Mn1 N2 2.029(2) . ?
Mn1 S1 2.3001(8) . ?
Mn1 Br1 2.5564(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
N1 C1 C2 123.3(2) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C1 C2 C3 118.8(2) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C2 C3 C4 118.9(2) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 119.4(2) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
N1 C5 C4 121.8(2) . . ?
N1 C5 C6 114.0(2) . . ?
C4 C5 C6 124.2(2) . . ?
N2 C6 C5 114.0(2) . . ?
N2 C6 C7 127.0(2) . . ?
C5 C6 C7 118.9(2) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 118.4(2) . . ?
C13 C8 N2 117.0(2) . . ?
C9 C8 N2 124.4(2) . . ?
C10 C9 C8 120.2(2) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 120.8(2) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 119.6(2) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 119.6(2) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C8 C13 C12 120.9(2) . . ?
C8 C13 S1 118.54(18) . . ?
C12 C13 S1 120.49(19) . . ?
S1 C14 H14A 109.5 . . ?
S1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
S1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 C15 Mn1 176.4(2) . . ?
O2 C16 Mn1 175.6(2) . . ?
C15 Mn1 C16 87.15(11) . . ?
C15 Mn1 N1 96.67(10) . . ?
C16 Mn1 N1 94.56(9) . . ?
C15 Mn1 N2 173.18(10) . . ?
C16 Mn1 N2 98.49(9) . . ?
N1 Mn1 N2 79.14(8) . . ?
C15 Mn1 S1 99.03(8) . . ?
C16 Mn1 S1 95.00(8) . . ?
N1 Mn1 S1 161.98(6) . . ?
N2 Mn1 S1 84.36(6) . . ?
C15 Mn1 Br1 88.57(8) . . ?
C16 Mn1 Br1 174.98(8) . . ?
N1 Mn1 Br1 88.53(6) . . ?
N2 Mn1 Br1 85.96(6) . . ?
S1 Mn1 Br1 83.09(2) . . ?
C1 N1 C5 117.7(2) . . ?
C1 N1 Mn1 127.76(16) . . ?
C5 N1 Mn1 114.47(15) . . ?
C6 N2 C8 124.2(2) . . ?
C6 N2 Mn1 114.72(16) . . ?
C8 N2 Mn1 119.71(15) . . ?
C13 S1 C14 99.06(12) . . ?
C13 S1 Mn1 98.80(8) . . ?
C14 S1 Mn1 112.02(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -0.9(4) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C3 C4 C5 N1 -1.3(4) . . . . ?
C3 C4 C5 C6 176.0(2) . . . . ?
N1 C5 C6 N2 8.7(3) . . . . ?
C4 C5 C6 N2 -168.8(2) . . . . ?
N1 C5 C6 C7 -168.8(2) . . . . ?
C4 C5 C6 C7 13.7(4) . . . . ?
C13 C8 C9 C10 -5.7(4) . . . . ?
N2 C8 C9 C10 178.7(2) . . . . ?
C8 C9 C10 C11 -0.1(4) . . . . ?
C9 C10 C11 C12 4.1(4) . . . . ?
C10 C11 C12 C13 -2.2(4) . . . . ?
C9 C8 C13 C12 7.6(3) . . . . ?
N2 C8 C13 C12 -176.5(2) . . . . ?
C9 C8 C13 S1 -170.70(18) . . . . ?
N2 C8 C13 S1 5.2(3) . . . . ?
C11 C12 C13 C8 -3.7(4) . . . . ?
C11 C12 C13 S1 174.61(18) . . . . ?
O1 C15 Mn1 C16 -66(4) . . . . ?
O1 C15 Mn1 N1 28(4) . . . . ?
O1 C15 Mn1 N2 80(4) . . . . ?
O1 C15 Mn1 S1 -160(4) . . . . ?
O1 C15 Mn1 Br1 117(4) . . . . ?
O2 C16 Mn1 C15 -6(3) . . . . ?
O2 C16 Mn1 N1 -102(3) . . . . ?
O2 C16 Mn1 N2 178(100) . . . . ?
O2 C16 Mn1 S1 93(3) . . . . ?
O2 C16 Mn1 Br1 26(4) . . . . ?
C2 C1 N1 C5 0.1(3) . . . . ?
C2 C1 N1 Mn1 176.76(18) . . . . ?
C4 C5 N1 C1 1.0(3) . . . . ?
C6 C5 N1 C1 -176.6(2) . . . . ?
C4 C5 N1 Mn1 -176.07(18) . . . . ?
C6 C5 N1 Mn1 6.3(2) . . . . ?
C15 Mn1 N1 C1 -14.7(2) . . . . ?
C16 Mn1 N1 C1 73.0(2) . . . . ?
N2 Mn1 N1 C1 170.8(2) . . . . ?
S1 Mn1 N1 C1 -165.15(15) . . . . ?
Br1 Mn1 N1 C1 -103.06(19) . . . . ?
C15 Mn1 N1 C5 162.03(17) . . . . ?
C16 Mn1 N1 C5 -110.31(17) . . . . ?
N2 Mn1 N1 C5 -12.52(16) . . . . ?
S1 Mn1 N1 C5 11.6(3) . . . . ?
Br1 Mn1 N1 C5 73.65(15) . . . . ?
C5 C6 N2 C8 174.2(2) . . . . ?
C7 C6 N2 C8 -8.5(4) . . . . ?
C5 C6 N2 Mn1 -19.3(3) . . . . ?
C7 C6 N2 Mn1 157.9(2) . . . . ?
C13 C8 N2 C6 152.5(2) . . . . ?
C9 C8 N2 C6 -31.9(4) . . . . ?
C13 C8 N2 Mn1 -13.3(3) . . . . ?
C9 C8 N2 Mn1 162.25(18) . . . . ?
C15 Mn1 N2 C6 -34.6(9) . . . . ?
C16 Mn1 N2 C6 110.96(18) . . . . ?
N1 Mn1 N2 C6 17.91(17) . . . . ?
S1 Mn1 N2 C6 -154.81(17) . . . . ?
Br1 Mn1 N2 C6 -71.37(16) . . . . ?
C15 Mn1 N2 C8 132.5(8) . . . . ?
C16 Mn1 N2 C8 -81.91(18) . . . . ?
N1 Mn1 N2 C8 -174.96(18) . . . . ?
S1 Mn1 N2 C8 12.32(16) . . . . ?
Br1 Mn1 N2 C8 95.76(16) . . . . ?
C8 C13 S1 C14 117.7(2) . . . . ?
C12 C13 S1 C14 -60.7(2) . . . . ?
C8 C13 S1 Mn1 3.54(19) . . . . ?
C12 C13 S1 Mn1 -174.80(18) . . . . ?
C15 Mn1 S1 C13 178.52(11) . . . . ?
C16 Mn1 S1 C13 90.63(11) . . . . ?
N1 Mn1 S1 C13 -31.2(2) . . . . ?
N2 Mn1 S1 C13 -7.44(9) . . . . ?
Br1 Mn1 S1 C13 -94.04(8) . . . . ?
C15 Mn1 S1 C14 74.97(13) . . . . ?
C16 Mn1 S1 C14 -12.93(13) . . . . ?
N1 Mn1 S1 C14 -134.7(2) . . . . ?
N2 Mn1 S1 C14 -111.00(12) . . . . ?
Br1 Mn1 S1 C14 162.40(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.086
_database_code_depnum_ccdc_archive 'CCDC 988786'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_FPh-MnCO-a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H15 N2 F S 1-, Mn 2+, 3 CO, Br 1-'
_chemical_formula_sum            'C22 H15 Br F Mn N2 O3 S'
_chemical_formula_weight         541.27

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'
F F 0.0171 0.0103 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_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                   7.9074(5)
_cell_length_b                   21.6449(14)
_cell_length_c                   12.5018(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.094(2)
_cell_angle_gamma                90.00
_cell_volume                     2127.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    9960
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plates
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080
_exptl_absorpt_coefficient_mu    2.632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.769
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
SADABS.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(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  
'Nonius Kappa CCD with a Bruker Apex II detector'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49859
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_av_sigmaI/netI    0.0320
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         27.49
_reflns_number_total             4888
_reflns_number_gt                4060
_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Apex II release 2010, Bruker AXS, Inc.'
_computing_cell_refinement       'Apex II release 2010, Bruker AXS, Inc.'
_computing_data_reduction        'Apex II release 2010, Bruker AXS, Inc.'

_computing_structure_solution    
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'XL SHELXTL/PC, Siemens Analytical'







_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0367P)²+0.1867P] 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         4888
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0710
_refine_ls_wR_factor_gt          0.0661
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_restrained_S_all      1.121
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8122(2) 0.70949(9) 0.11608(15) 0.0155(4) Uani 1 1 d . . .
C2 C 0.9044(3) 0.76381(10) 0.13842(16) 0.0203(4) Uani 1 1 d . . .
H2 H 0.9768 0.7787 0.0882 0.024 Uiso 1 1 calc R . .
C3 C 0.8921(3) 0.79617(10) 0.23184(17) 0.0227(5) Uani 1 1 d . . .
H3 H 0.9542 0.8334 0.2464 0.027 Uiso 1 1 calc R . .
C4 C 0.7873(3) 0.77317(10) 0.30387(16) 0.0192(4) Uani 1 1 d . . .
H4 H 0.7774 0.7936 0.3702 0.023 Uiso 1 1 calc R . .
C5 C 0.6972(3) 0.71983(9) 0.27726(15) 0.0156(4) Uani 1 1 d . . .
C6 C 0.5780(3) 0.69494(10) 0.34675(15) 0.0166(4) Uani 1 1 d . . .
H6 H 0.5706 0.7118 0.4163 0.020 Uiso 1 1 calc R . .
C7 C 0.3569(3) 0.62822(10) 0.37871(15) 0.0167(4) Uani 1 1 d . . .
C8 C 0.4036(3) 0.60156(10) 0.47970(16) 0.0183(4) Uani 1 1 d . . .
C9 C 0.2739(3) 0.58150(11) 0.53919(17) 0.0242(5) Uani 1 1 d . . .
H9 H 0.3023 0.5636 0.6081 0.029 Uiso 1 1 calc R . .
C10 C 0.1052(3) 0.58742(12) 0.49913(18) 0.0284(5) Uani 1 1 d . . .
H10 H 0.0187 0.5731 0.5402 0.034 Uiso 1 1 calc R . .
C11 C 0.0613(3) 0.61413(12) 0.39949(18) 0.0285(5) Uani 1 1 d . . .
H11 H -0.0550 0.6186 0.3727 0.034 Uiso 1 1 calc R . .
C12 C 0.1864(3) 0.63409(10) 0.33943(16) 0.0204(5) Uani 1 1 d . . .
H12 H 0.1563 0.6520 0.2707 0.025 Uiso 1 1 calc R . .
C13 C 0.6221(3) 0.54355(11) 0.63912(17) 0.0269(5) Uani 1 1 d . . .
H13A H 0.5837 0.5666 0.6995 0.040 Uiso 1 1 calc R . .
H13B H 0.7373 0.5279 0.6593 0.040 Uiso 1 1 calc R . .
H13C H 0.5449 0.5088 0.6210 0.040 Uiso 1 1 calc R . .
C14 C 0.8406(2) 0.67467(10) 0.01747(15) 0.0149(4) Uani 1 1 d . . .
C15 C 0.9284(3) 0.61918(10) 0.02562(16) 0.0194(4) Uani 1 1 d . . .
H15 H 0.9560 0.6009 0.0943 0.023 Uiso 1 1 calc R . .
C16 C 0.9766(3) 0.58997(11) -0.06513(17) 0.0223(5) Uani 1 1 d . . .
H16 H 1.0370 0.5520 -0.0598 0.027 Uiso 1 1 calc R . .
C17 C 0.9340(3) 0.61787(11) -0.16316(17) 0.0249(5) Uani 1 1 d . . .
C18 C 0.8442(3) 0.67172(11) -0.17542(17) 0.0250(5) Uani 1 1 d . . .
H18 H 0.8141 0.6890 -0.2447 0.030 Uiso 1 1 calc R . .
C19 C 0.7982(3) 0.70051(10) -0.08363(16) 0.0201(4) Uani 1 1 d . . .
H19 H 0.7370 0.7383 -0.0900 0.024 Uiso 1 1 calc R . .
C20 C 0.5282(3) 0.60059(10) 0.01927(17) 0.0202(5) Uani 1 1 d . . .
C21 C 0.6573(3) 0.55750(10) 0.20318(17) 0.0214(5) Uani 1 1 d . . .
C22 C 0.3401(3) 0.56673(10) 0.15187(16) 0.0181(4) Uani 1 1 d . . .
N1 N 0.7048(2) 0.68792(8) 0.18413(12) 0.0133(3) Uani 1 1 d . . .
N2 N 0.4832(2) 0.64982(8) 0.31223(12) 0.0150(4) Uani 1 1 d . . .
O1 O 0.5208(2) 0.58510(8) -0.06856(12) 0.0312(4) Uani 1 1 d . . .
O2 O 0.7438(2) 0.51705(8) 0.22703(14) 0.0354(4) Uani 1 1 d . . .
O3 O 0.23225(19) 0.53106(7) 0.14433(12) 0.0270(4) Uani 1 1 d . . .
F1 F 0.98628(18) 0.59042(7) -0.25154(10) 0.0390(4) Uani 1 1 d . . .
S1 S 0.62242(7) 0.59378(3) 0.52423(4) 0.02558(14) Uani 1 1 d . . .
Mn1 Mn 0.51561(4) 0.620047(14) 0.16019(2) 0.01365(8) Uani 1 1 d . . .
Br1 Br 0.32594(3) 0.708932(10) 0.093800(16) 0.02063(7) 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
C1 N1 1.348(2) . ?
C1 C2 1.396(3) . ?
C1 C14 1.482(3) . ?
C2 C3 1.374(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.378(3) . ?
C4 H4 0.9500 . ?
C5 N1 1.361(2) . ?
C5 C6 1.452(3) . ?
C6 N2 1.278(3) . ?
C6 H6 0.9500 . ?
C7 C12 1.391(3) . ?
C7 C8 1.402(3) . ?
C7 N2 1.443(2) . ?
C8 C9 1.398(3) . ?
C8 S1 1.768(2) . ?
C9 C10 1.380(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.384(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.374(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 S1 1.802(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.386(3) . ?
C14 C19 1.390(3) . ?
C15 C16 1.387(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.376(3) . ?
C16 H16 0.9500 . ?
C17 F1 1.357(2) . ?
C17 C18 1.365(3) . ?
C18 C19 1.388(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 O1 1.144(2) . ?
C20 Mn1 1.824(2) . ?
C21 O2 1.132(3) . ?
C21 Mn1 1.802(2) . ?
C22 O3 1.147(2) . ?
C22 Mn1 1.799(2) . ?
N1 Mn1 2.0954(16) . ?
N2 Mn1 2.0488(16) . ?
Mn1 Br1 2.5250(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 121.08(18) . . ?
N1 C1 C14 120.67(18) . . ?
C2 C1 C14 118.21(18) . . ?
C3 C2 C1 121.13(19) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 118.2(2) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C5 C4 C3 118.38(19) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
N1 C5 C4 124.28(18) . . ?
N1 C5 C6 114.46(17) . . ?
C4 C5 C6 121.19(18) . . ?
N2 C6 C5 118.45(18) . . ?
N2 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
C12 C7 C8 120.56(19) . . ?
C12 C7 N2 118.11(17) . . ?
C8 C7 N2 121.32(18) . . ?
C9 C8 C7 118.0(2) . . ?
C9 C8 S1 123.46(16) . . ?
C7 C8 S1 118.57(16) . . ?
C10 C9 C8 120.9(2) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 120.4(2) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 119.8(2) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C7 120.4(2) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
S1 C13 H13A 109.5 . . ?
S1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
S1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 119.08(19) . . ?
C15 C14 C1 119.91(17) . . ?
C19 C14 C1 120.56(19) . . ?
C14 C15 C16 120.9(2) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C15 117.8(2) . . ?
C17 C16 H16 121.1 . . ?
C15 C16 H16 121.1 . . ?
F1 C17 C18 118.8(2) . . ?
F1 C17 C16 117.8(2) . . ?
C18 C17 C16 123.4(2) . . ?
C17 C18 C19 118.0(2) . . ?
C17 C18 H18 121.0 . . ?
C19 C18 H18 121.0 . . ?
C18 C19 C14 120.8(2) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
O1 C20 Mn1 172.95(19) . . ?
O2 C21 Mn1 177.5(2) . . ?
O3 C22 Mn1 177.12(19) . . ?
C1 N1 C5 116.88(17) . . ?
C1 N1 Mn1 129.86(13) . . ?
C5 N1 Mn1 112.50(13) . . ?
C6 N2 C7 118.03(16) . . ?
C6 N2 Mn1 115.28(13) . . ?
C7 N2 Mn1 126.49(13) . . ?
C8 S1 C13 102.94(10) . . ?
C22 Mn1 C21 89.24(9) . . ?
C22 Mn1 C20 85.23(9) . . ?
C21 Mn1 C20 91.08(10) . . ?
C22 Mn1 N2 94.80(8) . . ?
C21 Mn1 N2 95.42(8) . . ?
C20 Mn1 N2 173.50(8) . . ?
C22 Mn1 N1 172.95(8) . . ?
C21 Mn1 N1 94.15(8) . . ?
C20 Mn1 N1 100.87(8) . . ?
N2 Mn1 N1 78.73(6) . . ?
C22 Mn1 Br1 92.41(7) . . ?
C21 Mn1 Br1 177.45(7) . . ?
C20 Mn1 Br1 87.12(7) . . ?
N2 Mn1 Br1 86.38(5) . . ?
N1 Mn1 Br1 84.43(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 1.8(3) . . . . ?
C14 C1 C2 C3 -175.8(2) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C2 C3 C4 C5 -1.5(3) . . . . ?
C3 C4 C5 N1 0.1(3) . . . . ?
C3 C4 C5 C6 -176.7(2) . . . . ?
N1 C5 C6 N2 -5.5(3) . . . . ?
C4 C5 C6 N2 171.69(19) . . . . ?
C12 C7 C8 C9 -0.3(3) . . . . ?
N2 C7 C8 C9 -179.73(19) . . . . ?
C12 C7 C8 S1 178.65(16) . . . . ?
N2 C7 C8 S1 -0.8(3) . . . . ?
C7 C8 C9 C10 0.5(3) . . . . ?
S1 C8 C9 C10 -178.39(18) . . . . ?
C8 C9 C10 C11 -0.8(4) . . . . ?
C9 C10 C11 C12 0.9(4) . . . . ?
C10 C11 C12 C7 -0.7(4) . . . . ?
C8 C7 C12 C11 0.4(3) . . . . ?
N2 C7 C12 C11 179.9(2) . . . . ?
N1 C1 C14 C15 -69.9(3) . . . . ?
C2 C1 C14 C15 107.7(2) . . . . ?
N1 C1 C14 C19 117.9(2) . . . . ?
C2 C1 C14 C19 -64.5(3) . . . . ?
C19 C14 C15 C16 1.1(3) . . . . ?
C1 C14 C15 C16 -171.20(19) . . . . ?
C14 C15 C16 C17 -0.1(3) . . . . ?
C15 C16 C17 F1 177.75(19) . . . . ?
C15 C16 C17 C18 -1.5(3) . . . . ?
F1 C17 C18 C19 -177.26(19) . . . . ?
C16 C17 C18 C19 1.9(3) . . . . ?
C17 C18 C19 C14 -0.8(3) . . . . ?
C15 C14 C19 C18 -0.6(3) . . . . ?
C1 C14 C19 C18 171.65(19) . . . . ?
C2 C1 N1 C5 -3.1(3) . . . . ?
C14 C1 N1 C5 174.43(17) . . . . ?
C2 C1 N1 Mn1 166.04(15) . . . . ?
C14 C1 N1 Mn1 -16.4(3) . . . . ?
C4 C5 N1 C1 2.2(3) . . . . ?
C6 C5 N1 C1 179.27(17) . . . . ?
C4 C5 N1 Mn1 -168.77(16) . . . . ?
C6 C5 N1 Mn1 8.3(2) . . . . ?
C5 C6 N2 C7 -175.74(17) . . . . ?
C5 C6 N2 Mn1 -0.5(2) . . . . ?
C12 C7 N2 C6 115.9(2) . . . . ?
C8 C7 N2 C6 -64.7(3) . . . . ?
C12 C7 N2 Mn1 -58.8(2) . . . . ?
C8 C7 N2 Mn1 120.65(18) . . . . ?
C9 C8 S1 C13 11.0(2) . . . . ?
C7 C8 S1 C13 -167.89(17) . . . . ?
C6 N2 Mn1 C22 -173.34(15) . . . . ?
C7 N2 Mn1 C22 1.49(17) . . . . ?
C6 N2 Mn1 C21 96.97(16) . . . . ?
C7 N2 Mn1 C21 -88.20(17) . . . . ?
C6 N2 Mn1 N1 3.81(14) . . . . ?
C7 N2 Mn1 N1 178.64(16) . . . . ?
C6 N2 Mn1 Br1 -81.22(14) . . . . ?
C7 N2 Mn1 Br1 93.61(15) . . . . ?
C1 N1 Mn1 C21 89.16(18) . . . . ?
C5 N1 Mn1 C21 -101.31(14) . . . . ?
C1 N1 Mn1 C20 -2.73(19) . . . . ?
C5 N1 Mn1 C20 166.79(14) . . . . ?
C1 N1 Mn1 N2 -176.12(18) . . . . ?
C5 N1 Mn1 N2 -6.60(13) . . . . ?
C1 N1 Mn1 Br1 -88.72(17) . . . . ?
C5 N1 Mn1 Br1 80.81(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.072
_database_code_depnum_ccdc_archive 'CCDC 988787'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_FPh-MnCO-b

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
; 
0.96 (C19 H15 N2 F S 1-, Mn 2+, Br 1-, 2 C O), 
 0.04 (C19 H15 N2 F S 1-, Mn 2+, Br 1-, C O)
;
_chemical_formula_sum            'C20.96 H15 Br F Mn N2 O1.96 S'
_chemical_formula_weight         512.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   13.942(5)
_cell_length_b                   11.412(5)
_cell_length_c                   14.573(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.66(3)
_cell_angle_gamma                90.00
_cell_volume                     2053.7(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4914
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       prisms
_exptl_crystal_colour            black
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1022
_exptl_absorpt_coefficient_mu    2.718
_exptl_absorpt_correction_type   multi-scans
_exptl_absorpt_correction_T_min  0.716
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
Abscor. T. Higashi (2001). The Rigaku Corporation, Tokyo, Japan.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Rigaku SCX-Mini with Mercury 2 CCD'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14241
_diffrn_reflns_av_R_equivalents  0.0861
_diffrn_reflns_av_sigmaI/netI    0.0882
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.16
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4679
_reflns_number_gt                3767
_reflns_threshold_expression     >2sigma(I)




_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'

_computing_structure_solution    
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'XP SHELXTL/PC, Siemens Analytical'





_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
	A large peak persisted in the difference electron density map 2.4 
Α from Mn.  Additional but much smaller peaks were observed near Br1.  These 
peaks were interpreted to be from a five coordinate Mn complex with one 
Br atom and one carbonyl group present in small quantities within the 
crystal.  As such, the structure was modeled as a disordered species where 
the lone carbonyl group resides near the Br atom of the six coordinate 
species.  The Br atom of the five coordinate species resides between the two 
carbonyl groups of the six coordinate complex.  The relative occupancies of 
the two species were estimated by assigning the variable x to the site 
occupancy for Br1 and (1-x) to the site occupancy for Br1a.  A common 
isotropic displacement parameter was refined for the two Br atoms while 
refining the variable x.  In this way, the site occupancy for Br1 refined 
to 96(1)%.  The ratio of the six coordinate species in the crystal to the 
five coordinate species is 24:1. 
	After an initial refinement, the coordinates for O1a and C2a were 
fixed along with their displacement parameters in the final refinement 
model.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0280P)²+3.6116P] 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         4679
_refine_ls_number_parameters     268
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1280
_refine_ls_wR_factor_gt          0.1205
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.76345(5) 0.53523(5) 0.52124(5) 0.02031(17) Uani 1 1 d D . .
Br1 Br 0.68240(3) 0.71800(4) 0.56190(3) 0.01991(13) Uani 0.96 1 d P A 1
Br1A Br 0.9467(9) 0.5387(10) 0.5668(9) 0.029(2) Uiso 0.04 1 d P A 2
O1A O 0.6920 0.7580 0.5682 0.020 Uiso 0.04 1 d PD A 2
C2A C 0.7345 0.6807 0.5520 0.020 Uiso 0.04 1 d PD A 2
S1 S 0.72445(9) 0.62931(9) 0.36776(9) 0.0242(2) Uani 1 1 d . A .
F1 F 1.2155(2) 0.6573(3) 0.9329(3) 0.0529(9) Uani 1 1 d . . .
O1 O 0.9858(3) 0.6282(3) 0.6161(3) 0.0400(9) Uani 0.96 1 d P . .
O2 O 0.8677(3) 0.3395(3) 0.4716(3) 0.0349(8) Uani 0.96 1 d PD . .
N1 N 0.7453(3) 0.4442(3) 0.6375(3) 0.0224(8) Uani 1 1 d . A .
N2 N 0.6149(3) 0.4653(3) 0.4376(3) 0.0201(7) Uani 1 1 d . A .
C1 C 0.9254(4) 0.6133(4) 0.7963(4) 0.0329(11) Uani 1 1 d . . .
H1A H 0.8609 0.6586 0.7669 0.039 Uiso 1 1 calc R . .
C2 C 1.0254(4) 0.6692(4) 0.8447(4) 0.0376(12) Uani 1 1 d . . .
H2A H 1.0299 0.7523 0.8474 0.045 Uiso 1 1 calc R . .
C3 C 1.1166(4) 0.6025(5) 0.8881(4) 0.0361(12) Uani 1 1 d . . .
C4 C 1.1151(4) 0.4821(4) 0.8873(4) 0.0375(12) Uani 1 1 d . . .
H4A H 1.1804 0.4383 0.9194 0.045 Uiso 1 1 calc R . .
C5 C 1.0154(4) 0.4266(4) 0.8382(4) 0.0339(11) Uani 1 1 d . . .
H5A H 1.0121 0.3434 0.8368 0.041 Uiso 1 1 calc R . .
C6 C 0.9192(4) 0.4921(4) 0.7906(3) 0.0272(10) Uani 1 1 d . A .
C7 C 0.8136(4) 0.4296(4) 0.7396(3) 0.0267(10) Uani 1 1 d . . .
C8 C 0.7874(4) 0.3554(4) 0.8017(4) 0.0382(12) Uani 1 1 d . A .
H8A H 0.8376 0.3455 0.8728 0.046 Uiso 1 1 calc R . .
C9 C 0.6898(4) 0.2967(4) 0.7610(4) 0.0403(13) Uani 1 1 d . . .
H9A H 0.6720 0.2466 0.8029 0.048 Uiso 1 1 calc R A .
C10 C 0.6187(4) 0.3131(4) 0.6574(4) 0.0305(10) Uani 1 1 d . A .
H10A H 0.5501 0.2754 0.6267 0.037 Uiso 1 1 calc R . .
C11 C 0.6492(3) 0.3861(4) 0.5986(3) 0.0235(9) Uani 1 1 d . . .
C12 C 0.5793(3) 0.4010(4) 0.4891(3) 0.0230(9) Uani 1 1 d . A .
H12A H 0.5099 0.3652 0.4559 0.028 Uiso 1 1 calc R . .
C13 C 0.5549(3) 0.4814(3) 0.3290(3) 0.0215(9) Uani 1 1 d . . .
C14 C 0.4574(3) 0.4244(4) 0.2652(3) 0.0255(9) Uani 1 1 d . A .
H14A H 0.4263 0.3724 0.2950 0.031 Uiso 1 1 calc R . .
C15 C 0.4059(4) 0.4430(4) 0.1596(4) 0.0339(11) Uani 1 1 d . . .
H15A H 0.3395 0.4043 0.1173 0.041 Uiso 1 1 calc R A .
C16 C 0.4514(4) 0.5193(4) 0.1146(4) 0.0384(12) Uani 1 1 d . A .
H16A H 0.4161 0.5316 0.0418 0.046 Uiso 1 1 calc R . .
C17 C 0.5489(4) 0.5771(4) 0.1770(3) 0.0297(10) Uani 1 1 d . . .
H17A H 0.5800 0.6291 0.1472 0.036 Uiso 1 1 calc R A .
C18 C 0.5993(3) 0.5572(4) 0.2829(3) 0.0244(9) Uani 1 1 d . A .
C19 C 0.8109(4) 0.5796(4) 0.3127(4) 0.0327(11) Uani 1 1 d . . .
H19A H 0.7918 0.6216 0.2478 0.049 Uiso 1 1 calc R A .
H19B H 0.8007 0.4953 0.2988 0.049 Uiso 1 1 calc R . .
H19C H 0.8868 0.5952 0.3617 0.049 Uiso 1 1 calc R . .
C20 C 0.8990(4) 0.5943(4) 0.5855(4) 0.0263(10) Uani 0.96 1 d P A .
C21 C 0.8245(3) 0.4125(4) 0.4907(3) 0.0232(10) Uani 0.96 1 d PD A .


_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 C21 1.799(4) . ?
Mn1 C20 1.805(5) . ?
Mn1 C2A 1.8134(9) . ?
Mn1 N2 2.016(4) . ?
Mn1 N1 2.100(4) . ?
Mn1 S1 2.3069(14) . ?
Mn1 Br1A 2.323(12) . ?
Mn1 Br1 2.5690(10) . ?
Br1A C20 1.044(12) . ?
Br1A O1 1.221(12) . ?
Br1A C21 2.111(12) . ?
O1A C2A 1.1463(3) . ?
S1 C18 1.802(4) . ?
S1 C19 1.822(5) . ?
F1 C3 1.372(6) . ?
O1 C20 1.145(5) . ?
O2 C21 1.135(5) . ?
N1 C7 1.354(5) . ?
N1 C11 1.360(5) . ?
N2 C12 1.303(5) . ?
N2 C13 1.417(5) . ?
C1 C6 1.386(6) . ?
C1 C2 1.391(7) . ?
C1 H1A 0.9500 . ?
C2 C3 1.360(7) . ?
C2 H2A 0.9500 . ?
C3 C4 1.374(7) . ?
C4 C5 1.387(7) . ?
C4 H4A 0.9500 . ?
C5 C6 1.406(6) . ?
C5 H5A 0.9500 . ?
C6 C7 1.487(6) . ?
C7 C8 1.407(7) . ?
C8 C9 1.379(7) . ?
C8 H8A 0.9500 . ?
C9 C10 1.381(7) . ?
C9 H9A 0.9500 . ?
C10 C11 1.396(6) . ?
C10 H10A 0.9500 . ?
C11 C12 1.442(6) . ?
C12 H12A 0.9500 . ?
C13 C14 1.401(6) . ?
C13 C18 1.403(6) . ?
C14 C15 1.379(6) . ?
C14 H14A 0.9500 . ?
C15 C16 1.407(7) . ?
C15 H15A 0.9500 . ?
C16 C17 1.401(7) . ?
C16 H16A 0.9500 . ?
C17 C18 1.386(6) . ?
C17 H17A 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C21 Mn1 C20 85.3(2) . . ?
C21 Mn1 N2 90.76(17) . . ?
C20 Mn1 N2 174.32(19) . . ?
C2A Mn1 N2 103.17(10) . . ?
C21 Mn1 N1 93.58(17) . . ?
C20 Mn1 N1 104.80(18) . . ?
C2A Mn1 N1 97.47(10) . . ?
N2 Mn1 N1 79.48(14) . . ?
C21 Mn1 S1 92.74(14) . . ?
C20 Mn1 S1 92.74(16) . . ?
C2A Mn1 S1 80.44(4) . . ?
N2 Mn1 S1 83.36(11) . . ?
N1 Mn1 S1 161.77(10) . . ?
C2A Mn1 Br1A 104.8(3) . . ?
N2 Mn1 Br1A 149.8(3) . . ?
N1 Mn1 Br1A 107.8(3) . . ?
S1 Mn1 Br1A 90.1(3) . . ?
C21 Mn1 Br1 176.85(14) . . ?
C20 Mn1 Br1 92.49(15) . . ?
C2A Mn1 Br1 13.462(12) . . ?
N2 Mn1 Br1 91.29(10) . . ?
N1 Mn1 Br1 89.15(10) . . ?
S1 Mn1 Br1 85.11(4) . . ?
O1A C2A Mn1 161.93(2) . . ?
C18 S1 C19 100.6(2) . . ?
C18 S1 Mn1 99.78(15) . . ?
C19 S1 Mn1 112.09(16) . . ?
C7 N1 C11 116.9(4) . . ?
C7 N1 Mn1 131.4(3) . . ?
C11 N1 Mn1 111.7(3) . . ?
C12 N2 C13 122.1(4) . . ?
C12 N2 Mn1 115.7(3) . . ?
C13 N2 Mn1 122.1(3) . . ?
C6 C1 C2 120.5(4) . . ?
C6 C1 H1A 119.7 . . ?
C2 C1 H1A 119.7 . . ?
C3 C2 C1 118.7(5) . . ?
C3 C2 H2A 120.7 . . ?
C1 C2 H2A 120.7 . . ?
C2 C3 F1 118.8(5) . . ?
C2 C3 C4 123.3(5) . . ?
F1 C3 C4 117.9(4) . . ?
C3 C4 C5 118.0(4) . . ?
C3 C4 H4A 121.0 . . ?
C5 C4 H4A 121.0 . . ?
C4 C5 C6 120.6(4) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 H5A 119.7 . . ?
C1 C6 C5 118.9(4) . . ?
C1 C6 C7 121.9(4) . . ?
C5 C6 C7 119.2(4) . . ?
N1 C7 C8 121.4(4) . . ?
N1 C7 C6 121.2(4) . . ?
C8 C7 C6 117.4(4) . . ?
C9 C8 C7 121.0(5) . . ?
C9 C8 H8A 119.5 . . ?
C7 C8 H8A 119.5 . . ?
C8 C9 C10 117.9(5) . . ?
C8 C9 H9A 121.0 . . ?
C10 C9 H9A 121.0 . . ?
C9 C10 C11 118.9(4) . . ?
C9 C10 H10A 120.5 . . ?
C11 C10 H10A 120.5 . . ?
N1 C11 C10 123.8(4) . . ?
N1 C11 C12 115.7(4) . . ?
C10 C11 C12 120.5(4) . . ?
N2 C12 C11 117.4(4) . . ?
N2 C12 H12A 121.3 . . ?
C11 C12 H12A 121.3 . . ?
C14 C13 C18 118.5(4) . . ?
C14 C13 N2 124.7(4) . . ?
C18 C13 N2 116.8(4) . . ?
C15 C14 C13 120.7(4) . . ?
C15 C14 H14A 119.6 . . ?
C13 C14 H14A 119.6 . . ?
C14 C15 C16 120.1(4) . . ?
C14 C15 H15A 119.9 . . ?
C16 C15 H15A 119.9 . . ?
C17 C16 C15 120.0(4) . . ?
C17 C16 H16A 120.0 . . ?
C15 C16 H16A 120.0 . . ?
C18 C17 C16 118.9(4) . . ?
C18 C17 H17A 120.5 . . ?
C16 C17 H17A 120.5 . . ?
C17 C18 C13 121.7(4) . . ?
C17 C18 S1 121.2(3) . . ?
C13 C18 S1 117.1(3) . . ?
S1 C19 H19A 109.5 . . ?
S1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
S1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1 C20 Mn1 172.0(4) . . ?
O2 C21 Mn1 175.9(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C21 Mn1 Br1A C20 -170.8(8) . . . . ?
C2A Mn1 Br1A C20 16.0(7) . . . . ?
N2 Mn1 Br1A C20 173.0(4) . . . . ?
N1 Mn1 Br1A C20 -87.1(7) . . . . ?
S1 Mn1 Br1A C20 96.1(7) . . . . ?
Br1 Mn1 Br1A C20 11.6(8) . . . . ?
C21 Mn1 Br1A O1 -175.6(9) . . . . ?
C20 Mn1 Br1A O1 -4.9(4) . . . . ?
C2A Mn1 Br1A O1 11.1(8) . . . . ?
N2 Mn1 Br1A O1 168.2(3) . . . . ?
N1 Mn1 Br1A O1 -92.0(7) . . . . ?
S1 Mn1 Br1A O1 91.2(7) . . . . ?
Br1 Mn1 Br1A O1 6.7(8) . . . . ?
C20 Mn1 Br1A C21 170.8(8) . . . . ?
C2A Mn1 Br1A C21 -173.25(19) . . . . ?
N2 Mn1 Br1A C21 -16.2(7) . . . . ?
N1 Mn1 Br1A C21 83.7(3) . . . . ?
S1 Mn1 Br1A C21 -93.1(2) . . . . ?
Br1 Mn1 Br1A C21 -177.65(16) . . . . ?
C21 Mn1 C2A O1A 173.3(5) . . . . ?
C20 Mn1 C2A O1A -158.65(16) . . . . ?
N2 Mn1 C2A O1A 26.05(13) . . . . ?
N1 Mn1 C2A O1A -54.84(12) . . . . ?
S1 Mn1 C2A O1A 106.85(7) . . . . ?
Br1A Mn1 C2A O1A -165.6(3) . . . . ?
Br1 Mn1 C2A O1A -2.55(5) . . . . ?
C21 Mn1 S1 C18 83.3(2) . . . . ?
C20 Mn1 S1 C18 168.7(2) . . . . ?
C2A Mn1 S1 C18 -111.76(15) . . . . ?
N2 Mn1 S1 C18 -7.16(17) . . . . ?
N1 Mn1 S1 C18 -26.9(4) . . . . ?
Br1A Mn1 S1 C18 143.3(3) . . . . ?
Br1 Mn1 S1 C18 -99.03(15) . . . . ?
C21 Mn1 S1 C19 -22.4(2) . . . . ?
C20 Mn1 S1 C19 63.0(2) . . . . ?
C2A Mn1 S1 C19 142.52(18) . . . . ?
N2 Mn1 S1 C19 -112.9(2) . . . . ?
N1 Mn1 S1 C19 -132.6(4) . . . . ?
Br1A Mn1 S1 C19 37.6(3) . . . . ?
Br1 Mn1 S1 C19 155.25(18) . . . . ?
C21 Br1A O1 C20 -3.6(16) . . . . ?
Mn1 Br1A O1 C20 4.2(4) . . . . ?
C21 Mn1 N1 C7 87.2(4) . . . . ?
C20 Mn1 N1 C7 1.1(4) . . . . ?
C2A Mn1 N1 C7 -80.6(4) . . . . ?
N2 Mn1 N1 C7 177.3(4) . . . . ?
S1 Mn1 N1 C7 -162.7(3) . . . . ?
Br1A Mn1 N1 C7 27.6(5) . . . . ?
Br1 Mn1 N1 C7 -91.2(4) . . . . ?
C21 Mn1 N1 C11 -88.9(3) . . . . ?
C20 Mn1 N1 C11 -174.9(3) . . . . ?
C2A Mn1 N1 C11 103.3(3) . . . . ?
N2 Mn1 N1 C11 1.2(3) . . . . ?
S1 Mn1 N1 C11 21.2(5) . . . . ?
Br1A Mn1 N1 C11 -148.5(4) . . . . ?
Br1 Mn1 N1 C11 92.7(3) . . . . ?
C21 Mn1 N2 C12 93.1(3) . . . . ?
C2A Mn1 N2 C12 -95.7(3) . . . . ?
N1 Mn1 N2 C12 -0.4(3) . . . . ?
S1 Mn1 N2 C12 -174.2(3) . . . . ?
Br1A Mn1 N2 C12 107.1(6) . . . . ?
Br1 Mn1 N2 C12 -89.3(3) . . . . ?
C21 Mn1 N2 C13 -84.5(3) . . . . ?
C2A Mn1 N2 C13 86.7(3) . . . . ?
N1 Mn1 N2 C13 -178.0(3) . . . . ?
S1 Mn1 N2 C13 8.2(3) . . . . ?
Br1A Mn1 N2 C13 -70.5(7) . . . . ?
Br1 Mn1 N2 C13 93.1(3) . . . . ?
C6 C1 C2 C3 -1.3(8) . . . . ?
C1 C2 C3 F1 177.9(5) . . . . ?
C1 C2 C3 C4 -0.5(8) . . . . ?
C2 C3 C4 C5 1.0(8) . . . . ?
F1 C3 C4 C5 -177.4(4) . . . . ?
C3 C4 C5 C6 0.2(7) . . . . ?
C2 C1 C6 C5 2.5(7) . . . . ?
C2 C1 C6 C7 179.9(5) . . . . ?
C4 C5 C6 C1 -2.0(7) . . . . ?
C4 C5 C6 C7 -179.4(4) . . . . ?
C11 N1 C7 C8 1.6(6) . . . . ?
Mn1 N1 C7 C8 -174.3(3) . . . . ?
C11 N1 C7 C6 -178.0(4) . . . . ?
Mn1 N1 C7 C6 6.0(6) . . . . ?
C1 C6 C7 N1 62.3(6) . . . . ?
C5 C6 C7 N1 -120.4(5) . . . . ?
C1 C6 C7 C8 -117.4(5) . . . . ?
C5 C6 C7 C8 59.9(6) . . . . ?
N1 C7 C8 C9 -1.5(7) . . . . ?
C6 C7 C8 C9 178.3(5) . . . . ?
C7 C8 C9 C10 0.0(8) . . . . ?
C8 C9 C10 C11 1.1(7) . . . . ?
C7 N1 C11 C10 -0.5(6) . . . . ?
Mn1 N1 C11 C10 176.2(4) . . . . ?
C7 N1 C11 C12 -178.6(4) . . . . ?
Mn1 N1 C11 C12 -1.9(5) . . . . ?
C9 C10 C11 N1 -0.9(7) . . . . ?
C9 C10 C11 C12 177.1(4) . . . . ?
C13 N2 C12 C11 177.1(4) . . . . ?
Mn1 N2 C12 C11 -0.5(5) . . . . ?
N1 C11 C12 N2 1.7(6) . . . . ?
C10 C11 C12 N2 -176.5(4) . . . . ?
C12 N2 C13 C14 -5.1(6) . . . . ?
Mn1 N2 C13 C14 172.3(3) . . . . ?
C12 N2 C13 C18 177.0(4) . . . . ?
Mn1 N2 C13 C18 -5.5(5) . . . . ?
C18 C13 C14 C15 -0.4(6) . . . . ?
N2 C13 C14 C15 -178.2(4) . . . . ?
C13 C14 C15 C16 0.4(7) . . . . ?
C14 C15 C16 C17 -0.4(8) . . . . ?
C15 C16 C17 C18 0.4(7) . . . . ?
C16 C17 C18 C13 -0.4(7) . . . . ?
C16 C17 C18 S1 -179.7(4) . . . . ?
C14 C13 C18 C17 0.4(6) . . . . ?
N2 C13 C18 C17 178.4(4) . . . . ?
C14 C13 C18 S1 179.7(3) . . . . ?
N2 C13 C18 S1 -2.3(5) . . . . ?
C19 S1 C18 C17 -58.6(4) . . . . ?
Mn1 S1 C18 C17 -173.5(4) . . . . ?
C19 S1 C18 C13 122.1(4) . . . . ?
Mn1 S1 C18 C13 7.2(3) . . . . ?
C21 Br1A C20 O1 178.5(7) . . . . ?
Mn1 Br1A C20 O1 -174.7(5) . . . . ?
O1 Br1A C20 Mn1 174.7(5) . . . . ?
C21 Br1A C20 Mn1 -6.8(6) . . . . ?
C20 Mn1 C21 Br1A -4.0(4) . . . . ?
C2A Mn1 C21 Br1A 23.7(6) . . . . ?
N2 Mn1 C21 Br1A 171.9(3) . . . . ?
N1 Mn1 C21 Br1A -108.6(3) . . . . ?
S1 Mn1 C21 Br1A 88.5(3) . . . . ?
C20 Br1A C21 O2 -174.8(7) . . . . ?
Mn1 Br1A C21 O2 178.3(4) . . . . ?
C20 Br1A C21 Mn1 6.9(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.843
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.121


#==============================================================================
_database_code_depnum_ccdc_archive 'CCDC 988788'
