# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2025

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

data_emcmh240228
_database_code_depnum_ccdc_archive 'CCDC 2406903'
loop_
_audit_author_name
_audit_author_address
'Nathalie GRUBER'
;University of Strasbourg
France
;
_audit_update_record             
;
2024-12-02 deposited with the CCDC.	2025-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H24 Br Mn N2 O3 S, C7 H8'
_chemical_formula_sum            'C31 H32 Br Mn N2 O3 S'
_chemical_formula_weight         647.49

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'
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'
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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   7.999(2)
_cell_length_b                   14.802(5)
_cell_length_c                   12.675(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.389(11)
_cell_angle_gamma                90
_cell_volume                     1500.2(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1509
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      18.22

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.875
_shelx_estimated_absorpt_T_min   0.779
_shelx_estimated_absorpt_T_max   0.835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5628
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  triumph
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20413
_diffrn_reflns_av_unetI/netI     0.2212
_diffrn_reflns_av_R_equivalents  0.1450
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.607
_diffrn_reflns_theta_max         28.001
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7121
_reflns_number_gt                3558
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.906
_reflns_Friedel_fraction_max     0.969
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/3(Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0301P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1031 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(19)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         7121
_refine_ls_number_parameters     356
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1687
_refine_ls_R_factor_gt           0.0794
_refine_ls_wR_factor_ref         0.2173
_refine_ls_wR_factor_gt          0.1682
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_restrained_S_all      0.956
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.56574(19) 0.47990(16) 0.14232(12) 0.0327(4) Uani 1 1 d . . . . .
Br1 Br 0.40302(14) 0.48084(10) -0.03242(9) 0.0421(4) Uani 1 1 d . . . . .
C1 C 0.6770(16) 0.3599(9) 0.0965(11) 0.038(3) Uani 1 1 d . . . . .
N1 N 0.7589(13) 0.3399(8) 0.0075(9) 0.039(3) Uani 1 1 d . . . . .
C2 C 0.8131(18) 0.2520(9) 0.0052(13) 0.050(4) Uani 1 1 d . . . . .
H2 H 0.873088 0.224445 -0.050017 0.060 Uiso 1 1 calc R U . . .
C3 C 0.7665(18) 0.2120(10) 0.0946(12) 0.050(4) Uani 1 1 d . . . . .
H3 H 0.785121 0.150971 0.114985 0.060 Uiso 1 1 calc R U . . .
N2 N 0.6864(14) 0.2776(7) 0.1503(9) 0.041(3) Uani 1 1 d . . . . .
C4 C 0.7988(17) 0.4042(9) -0.0774(11) 0.042(3) Uani 1 1 d . . . . .
H4A H 0.708451 0.449652 -0.084430 0.051 Uiso 1 1 calc R U . . .
H4B H 0.805621 0.371399 -0.145210 0.051 Uiso 1 1 calc R U . . .
C5 C 0.9646(16) 0.4517(10) -0.0533(11) 0.050(4) Uani 1 1 d . . . . .
H5A H 1.055858 0.406641 -0.055948 0.061 Uiso 1 1 calc R U . . .
H5B H 0.984129 0.496982 -0.109168 0.061 Uiso 1 1 calc R U . . .
C6 C 0.9732(14) 0.4980(10) 0.0515(10) 0.043(4) Uani 1 1 d . . . . .
H6A H 1.073939 0.536796 0.056391 0.052 Uiso 1 1 calc R U . . .
H6B H 0.980534 0.452593 0.108798 0.052 Uiso 1 1 calc R U . . .
S1 S 0.7854(4) 0.5667(2) 0.0655(3) 0.0375(8) Uani 1 1 d . . . . .
C7 C 0.8552(16) 0.6471(10) 0.1615(11) 0.041(3) Uani 1 1 d . . . . .
C8 C 0.9738(16) 0.6328(9) 0.2374(11) 0.039(3) Uani 1 1 d . . . . .
H8 H 1.026791 0.575440 0.241337 0.047 Uiso 1 1 calc R U . . .
C9 C 1.021(2) 0.6988(11) 0.3095(14) 0.063(5) Uani 1 1 d . . . . .
H9 H 1.102138 0.686246 0.363442 0.076 Uiso 1 1 calc R U . . .
C10 C 0.946(2) 0.7851(12) 0.3015(14) 0.060(4) Uani 1 1 d . . . . .
H10 H 0.980697 0.832234 0.347937 0.072 Uiso 1 1 calc R U . . .
C11 C 0.824(2) 0.8001(10) 0.2263(13) 0.058(5) Uani 1 1 d . . . . .
H11 H 0.768631 0.856950 0.223887 0.070 Uiso 1 1 calc R U . . .
C12 C 0.7787(18) 0.7338(9) 0.1531(13) 0.044(4) Uani 1 1 d . . . . .
H12 H 0.698281 0.746069 0.098642 0.053 Uiso 1 1 calc R U . . .
C13 C 0.6194(17) 0.2603(8) 0.2530(11) 0.038(3) Uani 1 1 d . . . . .
C14 C 0.4578(17) 0.2271(9) 0.2581(11) 0.041(3) Uani 1 1 d . . . . .
C15 C 0.4009(19) 0.2076(10) 0.3585(13) 0.051(4) Uani 1 1 d . . . . .
H15 H 0.291535 0.183518 0.364919 0.061 Uiso 1 1 calc R U . . .
C16 C 0.4961(19) 0.2217(11) 0.4488(12) 0.046(4) Uani 1 1 d . . . . .
C17 C 0.657(2) 0.2509(10) 0.4366(12) 0.050(4) Uani 1 1 d . . . . .
H17 H 0.725917 0.257413 0.498157 0.060 Uiso 1 1 calc R U . . .
C18 C 0.7242(18) 0.2714(9) 0.3418(12) 0.043(4) Uani 1 1 d . . . . .
C19 C 0.3544(19) 0.2043(11) 0.1639(13) 0.058(4) Uani 1 1 d . . . . .
H19A H 0.352354 0.255701 0.115119 0.087 Uiso 1 1 calc R U . . .
H19B H 0.240224 0.190481 0.185074 0.087 Uiso 1 1 calc R U . . .
H19C H 0.402024 0.151550 0.128767 0.087 Uiso 1 1 calc R U . . .
C20 C 0.426(3) 0.1990(13) 0.5548(14) 0.080(6) Uani 1 1 d . . . . .
H20A H 0.304999 0.188746 0.547006 0.120 Uiso 1 1 calc R U . . .
H20B H 0.446529 0.249288 0.603675 0.120 Uiso 1 1 calc R U . . .
H20C H 0.479819 0.144293 0.582590 0.120 Uiso 1 1 calc R U . . .
C21 C 0.9024(16) 0.2987(11) 0.3311(14) 0.055(4) Uani 1 1 d . . . . .
H21A H 0.947254 0.319261 0.399606 0.083 Uiso 1 1 calc R U . . .
H21B H 0.909556 0.347942 0.279638 0.083 Uiso 1 1 calc R U . . .
H21C H 0.967653 0.246977 0.306911 0.083 Uiso 1 1 calc R U . . .
C22 C 0.3844(16) 0.4268(9) 0.1949(11) 0.037(3) Uani 1 1 d . . . . .
O1 O 0.2577(12) 0.4044(7) 0.2308(8) 0.052(3) Uani 1 1 d . . . . .
C23 C 0.6640(14) 0.4827(12) 0.2706(9) 0.035(3) Uani 1 1 d . . . . .
O2 O 0.7222(10) 0.4878(8) 0.3528(7) 0.046(2) Uani 1 1 d . . . . .
C24 C 0.4622(17) 0.5868(10) 0.1698(11) 0.042(3) Uani 1 1 d . . . . .
O3 O 0.3922(12) 0.6511(7) 0.1909(9) 0.055(3) Uani 1 1 d . . . . .
C25 C 0.3724(18) 0.4832(14) 0.6079(11) 0.054(3) Uani 1 1 d . . . . .
C26 C 0.313(2) 0.4666(15) 0.5062(13) 0.070(5) Uani 1 1 d . . . . .
H26 H 0.386367 0.441442 0.456022 0.084 Uiso 1 1 calc R U . . .
C27 C 0.154(2) 0.4855(15) 0.4770(12) 0.068(4) Uani 1 1 d . . . . .
H27 H 0.114748 0.469594 0.408161 0.082 Uiso 1 1 calc R U . . .
C28 C 0.048(2) 0.5268(12) 0.5438(15) 0.071(5) Uani 1 1 d . . . . .
H28 H -0.061843 0.543239 0.521025 0.086 Uiso 1 1 calc R U . . .
C29 C 0.104(2) 0.5443(10) 0.6460(14) 0.063(5) Uani 1 1 d . . . . .
H29 H 0.030228 0.570056 0.695157 0.075 Uiso 1 1 calc R U . . .
C30 C 0.265(2) 0.5251(9) 0.6770(13) 0.059(5) Uani 1 1 d . . . . .
H30 H 0.302911 0.540385 0.746208 0.071 Uiso 1 1 calc R U . . .
C31 C 0.550(2) 0.4593(16) 0.6401(14) 0.088(7) Uani 1 1 d . . . . .
H31A H 0.553678 0.438019 0.713359 0.132 Uiso 1 1 calc R U . . .
H31B H 0.621616 0.512863 0.633991 0.132 Uiso 1 1 calc R U . . .
H31C H 0.591427 0.411523 0.593864 0.132 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 C23 1.790(12) . ?
Mn1 C22 1.793(14) . ?
Mn1 C24 1.823(15) . ?
Mn1 C1 2.077(13) . ?
Mn1 S1 2.402(4) . ?
Mn1 Br1 2.542(2) . ?
C1 N1 1.351(16) . ?
C1 N2 1.397(17) . ?
N1 C2 1.371(17) . ?
N1 C4 1.477(17) . ?
C2 C3 1.34(2) . ?
C2 H2 0.9500 . ?
C3 N2 1.370(17) . ?
C3 H3 0.9500 . ?
N2 C13 1.442(16) . ?
C4 C5 1.525(18) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.495(18) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 S1 1.826(12) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
S1 C7 1.782(15) . ?
C7 C8 1.351(19) . ?
C7 C12 1.424(19) . ?
C8 C9 1.38(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.41(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.37(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.39(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.386(18) . ?
C13 C18 1.40(2) . ?
C14 C15 1.39(2) . ?
C14 C19 1.475(19) . ?
C15 C16 1.37(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.37(2) . ?
C16 C20 1.507(19) . ?
C17 C18 1.363(19) . ?
C17 H17 0.9500 . ?
C18 C21 1.491(19) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 O1 1.169(15) . ?
C23 O2 1.133(13) . ?
C24 O3 1.139(16) . ?
C25 C26 1.38(2) . ?
C25 C30 1.39(2) . ?
C25 C31 1.51(2) . ?
C26 C27 1.35(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.36(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.39(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.36(2) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 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
C23 Mn1 C22 90.8(6) . . ?
C23 Mn1 C24 89.9(7) . . ?
C22 Mn1 C24 86.2(6) . . ?
C23 Mn1 C1 95.3(6) . . ?
C22 Mn1 C1 94.9(5) . . ?
C24 Mn1 C1 174.7(6) . . ?
C23 Mn1 S1 92.7(4) . . ?
C22 Mn1 S1 172.7(4) . . ?
C24 Mn1 S1 87.3(4) . . ?
C1 Mn1 S1 91.2(4) . . ?
C23 Mn1 Br1 175.0(3) . . ?
C22 Mn1 Br1 85.7(5) . . ?
C24 Mn1 Br1 86.4(4) . . ?
C1 Mn1 Br1 88.6(4) . . ?
S1 Mn1 Br1 90.44(11) . . ?
N1 C1 N2 101.3(11) . . ?
N1 C1 Mn1 129.9(10) . . ?
N2 C1 Mn1 128.9(10) . . ?
C1 N1 C2 112.7(11) . . ?
C1 N1 C4 125.8(11) . . ?
C2 N1 C4 121.5(11) . . ?
C3 C2 N1 107.9(12) . . ?
C3 C2 H2 126.1 . . ?
N1 C2 H2 126.1 . . ?
C2 C3 N2 105.4(13) . . ?
C2 C3 H3 127.3 . . ?
N2 C3 H3 127.3 . . ?
C3 N2 C1 112.7(12) . . ?
C3 N2 C13 121.9(12) . . ?
C1 N2 C13 125.4(11) . . ?
N1 C4 C5 110.7(12) . . ?
N1 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C6 C5 C4 114.2(10) . . ?
C6 C5 H5A 108.7 . . ?
C4 C5 H5A 108.7 . . ?
C6 C5 H5B 108.7 . . ?
C4 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C5 C6 S1 108.7(9) . . ?
C5 C6 H6A 109.9 . . ?
S1 C6 H6A 109.9 . . ?
C5 C6 H6B 109.9 . . ?
S1 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
C7 S1 C6 101.1(7) . . ?
C7 S1 Mn1 107.5(4) . . ?
C6 S1 Mn1 110.7(5) . . ?
C8 C7 C12 119.1(14) . . ?
C8 C7 S1 125.8(11) . . ?
C12 C7 S1 115.1(12) . . ?
C7 C8 C9 122.4(14) . . ?
C7 C8 H8 118.8 . . ?
C9 C8 H8 118.8 . . ?
C8 C9 C10 118.9(16) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C11 C10 C9 119.5(16) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 121.2(15) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C7 118.8(15) . . ?
C11 C12 H12 120.6 . . ?
C7 C12 H12 120.6 . . ?
C14 C13 C18 123.2(13) . . ?
C14 C13 N2 118.1(12) . . ?
C18 C13 N2 118.5(12) . . ?
C13 C14 C15 116.2(13) . . ?
C13 C14 C19 123.3(13) . . ?
C15 C14 C19 120.2(13) . . ?
C16 C15 C14 122.9(14) . . ?
C16 C15 H15 118.6 . . ?
C14 C15 H15 118.6 . . ?
C17 C16 C15 117.2(13) . . ?
C17 C16 C20 122.9(16) . . ?
C15 C16 C20 119.8(15) . . ?
C18 C17 C16 124.2(15) . . ?
C18 C17 H17 117.9 . . ?
C16 C17 H17 117.9 . . ?
C17 C18 C13 116.2(13) . . ?
C17 C18 C21 122.7(14) . . ?
C13 C18 C21 121.0(14) . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O1 C22 Mn1 170.4(11) . . ?
O2 C23 Mn1 177.0(15) . . ?
O3 C24 Mn1 176.2(12) . . ?
C26 C25 C30 117.6(16) . . ?
C26 C25 C31 120.5(16) . . ?
C30 C25 C31 121.9(15) . . ?
C27 C26 C25 121.2(17) . . ?
C27 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C26 C27 C28 121.5(17) . . ?
C26 C27 H27 119.2 . . ?
C28 C27 H27 119.2 . . ?
C27 C28 C29 118.3(18) . . ?
C27 C28 H28 120.9 . . ?
C29 C28 H28 120.9 . . ?
C30 C29 C28 120.8(17) . . ?
C30 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
C29 C30 C25 120.4(16) . . ?
C29 C30 H30 119.8 . . ?
C25 C30 H30 119.8 . . ?
C25 C31 H31A 109.5 . . ?
C25 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C25 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C1 N1 C2 0.8(15) . . . . ?
Mn1 C1 N1 C2 -179.1(10) . . . . ?
N2 C1 N1 C4 -175.4(12) . . . . ?
Mn1 C1 N1 C4 5(2) . . . . ?
C1 N1 C2 C3 0.1(17) . . . . ?
C4 N1 C2 C3 176.5(13) . . . . ?
N1 C2 C3 N2 -0.9(17) . . . . ?
C2 C3 N2 C1 1.4(18) . . . . ?
C2 C3 N2 C13 -179.1(13) . . . . ?
N1 C1 N2 C3 -1.4(16) . . . . ?
Mn1 C1 N2 C3 178.5(10) . . . . ?
N1 C1 N2 C13 179.2(12) . . . . ?
Mn1 C1 N2 C13 -1(2) . . . . ?
C1 N1 C4 C5 87.1(16) . . . . ?
C2 N1 C4 C5 -88.8(16) . . . . ?
N1 C4 C5 C6 -54.9(16) . . . . ?
C4 C5 C6 S1 -48.8(15) . . . . ?
C5 C6 S1 C7 -157.4(10) . . . . ?
C5 C6 S1 Mn1 88.9(9) . . . . ?
C6 S1 C7 C8 -29.0(13) . . . . ?
Mn1 S1 C7 C8 87.0(12) . . . . ?
C6 S1 C7 C12 149.5(10) . . . . ?
Mn1 S1 C7 C12 -94.5(10) . . . . ?
C12 C7 C8 C9 2(2) . . . . ?
S1 C7 C8 C9 -179.8(11) . . . . ?
C7 C8 C9 C10 -2(2) . . . . ?
C8 C9 C10 C11 3(2) . . . . ?
C9 C10 C11 C12 -4(2) . . . . ?
C10 C11 C12 C7 4(2) . . . . ?
C8 C7 C12 C11 -3(2) . . . . ?
S1 C7 C12 C11 178.9(10) . . . . ?
C3 N2 C13 C14 -87.8(16) . . . . ?
C1 N2 C13 C14 91.6(16) . . . . ?
C3 N2 C13 C18 87.5(16) . . . . ?
C1 N2 C13 C18 -93.2(16) . . . . ?
C18 C13 C14 C15 2.2(19) . . . . ?
N2 C13 C14 C15 177.2(11) . . . . ?
C18 C13 C14 C19 -171.9(13) . . . . ?
N2 C13 C14 C19 3(2) . . . . ?
C13 C14 C15 C16 1(2) . . . . ?
C19 C14 C15 C16 175.5(14) . . . . ?
C14 C15 C16 C17 -4(2) . . . . ?
C14 C15 C16 C20 179.9(14) . . . . ?
C15 C16 C17 C18 4(2) . . . . ?
C20 C16 C17 C18 179.6(16) . . . . ?
C16 C17 C18 C13 -1(2) . . . . ?
C16 C17 C18 C21 -176.9(14) . . . . ?
C14 C13 C18 C17 -2.6(19) . . . . ?
N2 C13 C18 C17 -177.6(12) . . . . ?
C14 C13 C18 C21 173.9(13) . . . . ?
N2 C13 C18 C21 -1.1(18) . . . . ?
C30 C25 C26 C27 -4(3) . . . . ?
C31 C25 C26 C27 178.4(19) . . . . ?
C25 C26 C27 C28 4(4) . . . . ?
C26 C27 C28 C29 -4(3) . . . . ?
C27 C28 C29 C30 4(3) . . . . ?
C28 C29 C30 C25 -3(2) . . . . ?
C26 C25 C30 C29 3(3) . . . . ?
C31 C25 C30 C29 -178.9(17) . . . . ?

_refine_diff_density_max         1.431
_refine_diff_density_min         -0.838
_refine_diff_density_rms         0.135



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

data_emcmh231011-02
_database_code_depnum_ccdc_archive 'CCDC 2406906'
loop_
_audit_author_name
_audit_author_address
'Nathalie GRUBER'
;University of Strasbourg
France
;
_audit_update_record             
;
2024-12-02 deposited with the CCDC.	2025-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H26 Br Mn N2 O3 S'
_chemical_formula_sum            'C21 H26 Br Mn N2 O3 S'
_chemical_formula_weight         521.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn -0.5299 2.8052 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   15.7798(7)
_cell_length_b                   8.0924(3)
_cell_length_c                   18.2707(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.904(2)
_cell_angle_gamma                90
_cell_volume                     2282.93(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9976
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      66.68

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    7.803
_shelx_estimated_absorpt_T_min   0.304
_shelx_estimated_absorpt_T_max   0.454
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4878
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Mo-ImuS 3.0 microfocus tube'
_diffrn_measurement_device_type  'Bruker PHOTON-III CPAD'
_diffrn_measurement_method       'φ and ω shuterless scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24271
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_av_R_equivalents  0.0733
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.862
_diffrn_reflns_theta_max         66.759
_diffrn_reflns_theta_full        66.759
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4019
_reflns_number_gt                3561
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/3(Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1487P)²+3.7043P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4019
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0657
_refine_ls_wR_factor_ref         0.2010
_refine_ls_wR_factor_gt          0.1925
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.23997(4) 0.63492(8) 0.27384(4) 0.0136(3) Uani 1 1 d . . . . .
Br1 Br 0.14904(3) 0.54448(7) 0.36582(3) 0.0281(2) Uani 1 1 d . . . . .
S1 S 0.10808(7) 0.72198(14) 0.19179(6) 0.0180(3) Uani 1 1 d . . . . .
C1 C 0.1100(3) 0.7525(7) 0.0910(3) 0.0255(11) Uani 1 1 d . . . . .
C2 C 0.1653(4) 0.8999(8) 0.0784(3) 0.0343(13) Uani 1 1 d . . . . .
H2A H 0.175364 0.896619 0.027273 0.051 Uiso 1 1 calc R U . . .
H2B H 0.220970 0.895370 0.114050 0.051 Uiso 1 1 calc R U . . .
H2C H 0.135222 1.002553 0.085846 0.051 Uiso 1 1 calc R U . . .
C3 C 0.0159(4) 0.7753(8) 0.0494(3) 0.0340(13) Uani 1 1 d . . . . .
H3A H -0.010643 0.865915 0.072390 0.051 Uiso 1 1 calc R U . . .
H3B H -0.016543 0.673126 0.052477 0.051 Uiso 1 1 calc R U . . .
H3C H 0.014631 0.801583 -0.003132 0.051 Uiso 1 1 calc R U . . .
C4 C 0.1470(4) 0.5934(8) 0.0643(3) 0.0329(12) Uani 1 1 d . . . . .
H4A H 0.136836 0.593236 0.009552 0.049 Uiso 1 1 calc R U . . .
H4B H 0.118357 0.497478 0.081289 0.049 Uiso 1 1 calc R U . . .
H4C H 0.209345 0.587888 0.085012 0.049 Uiso 1 1 calc R U . . .
C5 C 0.0788(3) 0.9281(7) 0.2179(3) 0.0256(11) Uani 1 1 d . . . . .
H5A H 0.114017 1.011588 0.198102 0.031 Uiso 1 1 calc R U . . .
H5B H 0.017003 0.949625 0.195965 0.031 Uiso 1 1 calc R U . . .
C6 C 0.0942(3) 0.9422(6) 0.3024(3) 0.0246(11) Uani 1 1 d . . . . .
H6A H 0.060934 1.037083 0.316043 0.030 Uiso 1 1 calc R U . . .
H6B H 0.073175 0.840806 0.323233 0.030 Uiso 1 1 calc R U . . .
N1 N 0.1866(3) 0.9653(5) 0.3350(2) 0.0172(8) Uani 1 1 d . . . . .
C7 C 0.2510(3) 0.8591(5) 0.3289(2) 0.0145(9) Uani 1 1 d . . . . .
N2 N 0.3233(3) 0.9370(5) 0.3683(2) 0.0153(8) Uani 1 1 d . . . . .
C8 C 0.3024(3) 1.0854(6) 0.3976(3) 0.0223(10) Uani 1 1 d . . . . .
H8 H 0.341783 1.160245 0.426857 0.027 Uiso 1 1 calc R U . . .
C9 C 0.2170(3) 1.1042(6) 0.3774(3) 0.0240(11) Uani 1 1 d . . . . .
H9 H 0.183533 1.193958 0.389501 0.029 Uiso 1 1 calc R U . . .
C10 C 0.4113(3) 0.8764(5) 0.3832(3) 0.0149(9) Uani 1 1 d . . . . .
C11 C 0.4664(3) 0.9236(6) 0.3358(3) 0.0173(9) Uani 1 1 d . . . . .
C12 C 0.5509(3) 0.8624(6) 0.3533(3) 0.0188(10) Uani 1 1 d . . . . .
H12 H 0.589755 0.891021 0.322005 0.023 Uiso 1 1 calc R U . . .
C13 C 0.5804(3) 0.7616(6) 0.4148(3) 0.0175(9) Uani 1 1 d . . . . .
C14 C 0.5241(3) 0.7239(6) 0.4617(2) 0.0169(9) Uani 1 1 d . . . . .
H14 H 0.543834 0.657091 0.504565 0.020 Uiso 1 1 calc R U . . .
C15 C 0.4389(3) 0.7826(5) 0.4470(2) 0.0152(9) Uani 1 1 d . . . . .
C16 C 0.4393(4) 1.0434(6) 0.2731(3) 0.0255(11) Uani 1 1 d . . . . .
H16A H 0.458309 1.154760 0.290154 0.038 Uiso 1 1 calc R U . . .
H16B H 0.376115 1.041749 0.257026 0.038 Uiso 1 1 calc R U . . .
H16C H 0.465800 1.012260 0.231087 0.038 Uiso 1 1 calc R U . . .
C17 C 0.6718(3) 0.6939(7) 0.4298(3) 0.0275(11) Uani 1 1 d . . . . .
H17A H 0.682543 0.639971 0.384526 0.041 Uiso 1 1 calc R U . . .
H17B H 0.678850 0.613273 0.470600 0.041 Uiso 1 1 calc R U . . .
H17C H 0.713041 0.784603 0.443849 0.041 Uiso 1 1 calc R U . . .
C18 C 0.3800(3) 0.7437(7) 0.5007(3) 0.0228(10) Uani 1 1 d . . . . .
H18A H 0.367536 0.845572 0.525555 0.034 Uiso 1 1 calc R U . . .
H18B H 0.408690 0.664491 0.538348 0.034 Uiso 1 1 calc R U . . .
H18C H 0.325736 0.696060 0.472954 0.034 Uiso 1 1 calc R U . . .
C19 C 0.3318(3) 0.5348(6) 0.3333(3) 0.0188(10) Uani 1 1 d . . . . .
O1 O 0.3878(2) 0.4576(4) 0.3645(2) 0.0265(8) Uani 1 1 d . . . . .
C20 C 0.3109(3) 0.6979(6) 0.2144(3) 0.0199(10) Uani 1 1 d . . . . .
O2 O 0.3600(2) 0.7308(5) 0.17784(19) 0.0263(8) Uani 1 1 d . . . . .
C21 C 0.2189(3) 0.4319(6) 0.2303(3) 0.0217(10) Uani 1 1 d . . . . .
O3 O 0.2073(3) 0.3017(5) 0.2062(2) 0.0342(9) 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
Mn1 C20 1.788(5) . ?
Mn1 C19 1.813(5) . ?
Mn1 C21 1.825(5) . ?
Mn1 C7 2.064(4) . ?
Mn1 S1 2.4059(13) . ?
Mn1 Br1 2.5325(8) . ?
S1 C5 1.821(5) . ?
S1 C1 1.864(5) . ?
C1 C2 1.524(8) . ?
C1 C3 1.533(7) . ?
C1 C4 1.534(8) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.516(7) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N1 1.470(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
N1 C7 1.352(6) . ?
N1 C9 1.393(6) . ?
C7 N2 1.372(6) . ?
N2 C8 1.382(6) . ?
N2 C10 1.444(6) . ?
C8 C9 1.331(8) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C15 1.384(6) . ?
C10 C11 1.401(6) . ?
C11 C12 1.396(7) . ?
C11 C16 1.494(7) . ?
C12 C13 1.388(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(7) . ?
C13 C17 1.514(6) . ?
C14 C15 1.398(7) . ?
C14 H14 0.9500 . ?
C15 C18 1.517(6) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 O1 1.135(6) . ?
C20 O2 1.153(6) . ?
C21 O3 1.143(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
C20 Mn1 C19 88.2(2) . . ?
C20 Mn1 C21 94.2(2) . . ?
C19 Mn1 C21 84.8(2) . . ?
C20 Mn1 C7 92.59(19) . . ?
C19 Mn1 C7 97.14(19) . . ?
C21 Mn1 C7 173.0(2) . . ?
C20 Mn1 S1 96.18(16) . . ?
C19 Mn1 S1 170.41(15) . . ?
C21 Mn1 S1 86.32(17) . . ?
C7 Mn1 S1 91.22(13) . . ?
C20 Mn1 Br1 175.81(16) . . ?
C19 Mn1 Br1 88.03(15) . . ?
C21 Mn1 Br1 87.23(15) . . ?
C7 Mn1 Br1 86.16(12) . . ?
S1 Mn1 Br1 87.84(4) . . ?
C5 S1 C1 101.2(2) . . ?
C5 S1 Mn1 109.79(17) . . ?
C1 S1 Mn1 117.80(17) . . ?
C2 C1 C3 110.9(5) . . ?
C2 C1 C4 109.9(4) . . ?
C3 C1 C4 109.7(5) . . ?
C2 C1 S1 112.3(4) . . ?
C3 C1 S1 107.1(4) . . ?
C4 C1 S1 106.7(4) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 S1 109.9(4) . . ?
C6 C5 H5A 109.7 . . ?
S1 C5 H5A 109.7 . . ?
C6 C5 H5B 109.7 . . ?
S1 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
N1 C6 C5 111.0(4) . . ?
N1 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
N1 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C7 N1 C9 112.4(4) . . ?
C7 N1 C6 125.8(4) . . ?
C9 N1 C6 121.8(4) . . ?
N1 C7 N2 102.8(4) . . ?
N1 C7 Mn1 127.6(3) . . ?
N2 C7 Mn1 129.6(3) . . ?
C7 N2 C8 111.3(4) . . ?
C7 N2 C10 127.3(4) . . ?
C8 N2 C10 121.3(4) . . ?
C9 C8 N2 107.6(4) . . ?
C9 C8 H8 126.2 . . ?
N2 C8 H8 126.2 . . ?
C8 C9 N1 105.9(4) . . ?
C8 C9 H9 127.1 . . ?
N1 C9 H9 127.1 . . ?
C15 C10 C11 122.8(4) . . ?
C15 C10 N2 118.0(4) . . ?
C11 C10 N2 119.1(4) . . ?
C12 C11 C10 116.5(4) . . ?
C12 C11 C16 120.9(4) . . ?
C10 C11 C16 122.4(4) . . ?
C13 C12 C11 122.6(4) . . ?
C13 C12 H12 118.7 . . ?
C11 C12 H12 118.7 . . ?
C12 C13 C14 118.5(4) . . ?
C12 C13 C17 120.4(4) . . ?
C14 C13 C17 121.0(4) . . ?
C13 C14 C15 121.2(4) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C10 C15 C14 118.1(4) . . ?
C10 C15 C18 122.0(4) . . ?
C14 C15 C18 119.9(4) . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O1 C19 Mn1 171.9(4) . . ?
O2 C20 Mn1 175.8(4) . . ?
O3 C21 Mn1 176.9(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
C5 S1 C1 C2 51.4(4) . . . . ?
Mn1 S1 C1 C2 -68.3(4) . . . . ?
C5 S1 C1 C3 -70.7(4) . . . . ?
Mn1 S1 C1 C3 169.7(3) . . . . ?
C5 S1 C1 C4 171.9(4) . . . . ?
Mn1 S1 C1 C4 52.2(4) . . . . ?
C1 S1 C5 C6 -166.6(4) . . . . ?
Mn1 S1 C5 C6 -41.4(4) . . . . ?
S1 C5 C6 N1 77.9(5) . . . . ?
C5 C6 N1 C7 -60.2(6) . . . . ?
C5 C6 N1 C9 120.5(5) . . . . ?
C9 N1 C7 N2 -0.7(5) . . . . ?
C6 N1 C7 N2 179.9(4) . . . . ?
C9 N1 C7 Mn1 178.8(3) . . . . ?
C6 N1 C7 Mn1 -0.5(7) . . . . ?
N1 C7 N2 C8 0.5(5) . . . . ?
Mn1 C7 N2 C8 -179.1(3) . . . . ?
N1 C7 N2 C10 177.3(4) . . . . ?
Mn1 C7 N2 C10 -2.3(7) . . . . ?
C7 N2 C8 C9 0.0(6) . . . . ?
C10 N2 C8 C9 -177.1(4) . . . . ?
N2 C8 C9 N1 -0.4(6) . . . . ?
C7 N1 C9 C8 0.7(6) . . . . ?
C6 N1 C9 C8 -179.9(4) . . . . ?
C7 N2 C10 C15 -89.2(6) . . . . ?
C8 N2 C10 C15 87.3(5) . . . . ?
C7 N2 C10 C11 95.1(5) . . . . ?
C8 N2 C10 C11 -88.4(5) . . . . ?
C15 C10 C11 C12 3.9(7) . . . . ?
N2 C10 C11 C12 179.4(4) . . . . ?
C15 C10 C11 C16 -171.4(4) . . . . ?
N2 C10 C11 C16 4.1(7) . . . . ?
C10 C11 C12 C13 -0.7(7) . . . . ?
C16 C11 C12 C13 174.7(4) . . . . ?
C11 C12 C13 C14 -1.8(7) . . . . ?
C11 C12 C13 C17 177.9(4) . . . . ?
C12 C13 C14 C15 1.4(7) . . . . ?
C17 C13 C14 C15 -178.3(4) . . . . ?
C11 C10 C15 C14 -4.3(7) . . . . ?
N2 C10 C15 C14 -179.9(4) . . . . ?
C11 C10 C15 C18 175.3(4) . . . . ?
N2 C10 C15 C18 -0.3(6) . . . . ?
C13 C14 C15 C10 1.5(7) . . . . ?
C13 C14 C15 C18 -178.1(4) . . . . ?

_refine_diff_density_max         1.299
_refine_diff_density_min         -1.710
_refine_diff_density_rms         0.204



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

data_emcmh231121sq
_database_code_depnum_ccdc_archive 'CCDC 2406904'
loop_
_audit_author_name
_audit_author_address
'Nathalie GRUBER'
;University of Strasbourg
France
;
_audit_update_record             
;
2024-12-02 deposited with the CCDC.	2025-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H18 Br Mn N2 O3 S, solvent'
_chemical_formula_sum            'C21 H18 Br Mn N2 O3 S, solvent'
_chemical_formula_weight         513.28

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1743(9)
_cell_length_b                   10.9691(11)
_cell_length_c                   12.8226(14)
_cell_angle_alpha                91.696(3)
_cell_angle_beta                 100.136(3)
_cell_angle_gamma                91.504(3)
_cell_volume                     1130.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5341
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      21.60

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_F_000             516
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.466
_shelx_estimated_absorpt_T_min   0.694
_shelx_estimated_absorpt_T_max   0.791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6597
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  triumph
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43287
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_av_R_equivalents  0.0878
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.614
_diffrn_reflns_theta_max         28.082
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5471
_reflns_number_gt                3739
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/3(Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1188P)²+3.2018P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5471
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0654
_refine_ls_wR_factor_ref         0.2108
_refine_ls_wR_factor_gt          0.1816
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.30841(9) 0.70523(7) 0.38346(6) 0.0213(2) Uani 1 1 d . . . . .
Br1 Br 0.08271(7) 0.85048(6) 0.40801(5) 0.0436(2) Uani 1 1 d . . . . .
C1 C 0.4182(6) 0.7393(5) 0.5383(4) 0.0232(10) Uani 1 1 d . . . . .
N1 N 0.5806(5) 0.7739(4) 0.5727(4) 0.0275(9) Uani 1 1 d . . . . .
C2 C 0.6175(7) 0.7840(6) 0.6818(4) 0.0335(13) Uani 1 1 d . . . . .
H2 H 0.722436 0.806603 0.723483 0.040 Uiso 1 1 calc R U . . .
C3 C 0.4764(7) 0.7557(5) 0.7182(4) 0.0317(12) Uani 1 1 d . . . . .
H3 H 0.462851 0.754209 0.790246 0.038 Uiso 1 1 calc R U . . .
N2 N 0.3553(5) 0.7291(4) 0.6298(3) 0.0235(9) Uani 1 1 d . . . . .
C4 C 0.7013(6) 0.8018(5) 0.5040(4) 0.0284(11) Uani 1 1 d . . . . .
H4A H 0.713302 0.728733 0.459125 0.034 Uiso 1 1 calc R U . . .
H4B H 0.810940 0.822131 0.548395 0.034 Uiso 1 1 calc R U . . .
C5 C 0.6491(7) 0.9071(5) 0.4338(4) 0.0313(12) Uani 1 1 d . . . . .
H5A H 0.738842 0.925964 0.393485 0.038 Uiso 1 1 calc R U . . .
H5B H 0.638216 0.979661 0.479553 0.038 Uiso 1 1 calc R U . . .
S1 S 0.45431(16) 0.88256(12) 0.33953(11) 0.0280(3) Uani 1 1 d . . . . .
C6 C 0.5237(7) 0.8519(6) 0.2173(4) 0.0320(12) Uani 1 1 d . . . . .
C7 C 0.6745(7) 0.8028(6) 0.2091(5) 0.0369(13) Uani 1 1 d . . . . .
H7 H 0.749725 0.782790 0.271064 0.044 Uiso 1 1 calc R U . . .
C8 C 0.7151(8) 0.7829(8) 0.1107(5) 0.0512(18) Uani 1 1 d . . . . .
H8 H 0.818665 0.748543 0.104766 0.061 Uiso 1 1 calc R U . . .
C9 C 0.6061(9) 0.8126(8) 0.0196(5) 0.057(2) Uani 1 1 d . . . . .
H9 H 0.636636 0.800071 -0.047977 0.068 Uiso 1 1 calc R U . . .
C10 C 0.4555(9) 0.8596(9) 0.0271(6) 0.063(2) Uani 1 1 d . . . . .
H10 H 0.379954 0.878281 -0.035120 0.075 Uiso 1 1 calc R U . . .
C11 C 0.4138(8) 0.8797(7) 0.1257(5) 0.0465(17) Uani 1 1 d . . . . .
H11 H 0.309340 0.912853 0.131252 0.056 Uiso 1 1 calc R U . . .
C12 C 0.1862(6) 0.6832(5) 0.6371(4) 0.0258(10) Uani 1 1 d . . . . .
H12A H 0.187832 0.593825 0.645612 0.031 Uiso 1 1 calc R U . . .
H12B H 0.109832 0.699189 0.570326 0.031 Uiso 1 1 calc R U . . .
C13 C 0.1214(6) 0.7427(5) 0.7291(4) 0.0245(10) Uani 1 1 d . . . . .
C14 C 0.0922(7) 0.8661(5) 0.7305(5) 0.0332(12) Uani 1 1 d . . . . .
H14 H 0.114432 0.914217 0.673916 0.040 Uiso 1 1 calc R U . . .
C15 C 0.0295(7) 0.9212(6) 0.8156(5) 0.0415(15) Uani 1 1 d . . . . .
H15 H 0.008815 1.006056 0.816419 0.050 Uiso 1 1 calc R U . . .
C16 C -0.0012(8) 0.8506(7) 0.8971(5) 0.0462(17) Uani 1 1 d . . . . .
H16 H -0.041934 0.887314 0.955138 0.055 Uiso 1 1 calc R U . . .
C17 C 0.0264(8) 0.7274(8) 0.8959(5) 0.0514(19) Uani 1 1 d . . . . .
H17 H 0.004041 0.679475 0.952552 0.062 Uiso 1 1 calc R U . . .
C18 C 0.0866(8) 0.6734(6) 0.8122(5) 0.0398(14) Uani 1 1 d . . . . .
H18 H 0.104332 0.588166 0.811399 0.048 Uiso 1 1 calc R U . . .
C19 C 0.4666(7) 0.6072(5) 0.3565(5) 0.0304(12) Uani 1 1 d . . . . .
O1 O 0.5639(6) 0.5414(4) 0.3366(4) 0.0521(12) Uani 1 1 d . . . . .
C20 C 0.1940(7) 0.6837(6) 0.2479(5) 0.0375(13) Uani 1 1 d . . . . .
O2 O 0.1168(7) 0.6657(6) 0.1657(4) 0.0633(15) Uani 1 1 d . . . . .
C21 C 0.2018(7) 0.5701(5) 0.4167(4) 0.0301(12) Uani 1 1 d . . . . .
O3 O 0.1406(6) 0.4776(4) 0.4335(4) 0.0458(11) 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
Mn1 C19 1.777(6) . ?
Mn1 C21 1.800(6) . ?
Mn1 C20 1.829(6) . ?
Mn1 C1 2.049(5) . ?
Mn1 S1 2.3881(15) . ?
Mn1 Br1 2.5240(10) . ?
C1 N1 1.364(6) . ?
C1 N2 1.367(6) . ?
N1 C2 1.378(7) . ?
N1 C4 1.466(6) . ?
C2 C3 1.351(7) . ?
C2 H2 0.9500 . ?
C3 N2 1.386(7) . ?
C3 H3 0.9500 . ?
N2 C12 1.478(6) . ?
C4 C5 1.509(8) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 S1 1.830(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
S1 C6 1.784(6) . ?
C6 C7 1.377(8) . ?
C6 C11 1.394(8) . ?
C7 C8 1.373(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.391(10) . ?
C8 H8 0.9500 . ?
C9 C10 1.365(11) . ?
C9 H9 0.9500 . ?
C10 C11 1.379(10) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.513(7) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.382(8) . ?
C13 C18 1.392(8) . ?
C14 C15 1.411(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.373(10) . ?
C15 H15 0.9500 . ?
C16 C17 1.376(11) . ?
C16 H16 0.9500 . ?
C17 C18 1.380(9) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 O1 1.144(7) . ?
C20 O2 1.138(7) . ?
C21 O3 1.162(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
C19 Mn1 C21 86.5(3) . . ?
C19 Mn1 C20 91.6(3) . . ?
C21 Mn1 C20 88.0(3) . . ?
C19 Mn1 C1 93.9(2) . . ?
C21 Mn1 C1 92.0(2) . . ?
C20 Mn1 C1 174.5(2) . . ?
C19 Mn1 S1 92.50(18) . . ?
C21 Mn1 S1 178.97(19) . . ?
C20 Mn1 S1 92.3(2) . . ?
C1 Mn1 S1 87.84(14) . . ?
C19 Mn1 Br1 175.70(19) . . ?
C21 Mn1 Br1 96.01(18) . . ?
C20 Mn1 Br1 85.00(19) . . ?
C1 Mn1 Br1 89.52(14) . . ?
S1 Mn1 Br1 85.00(4) . . ?
N1 C1 N2 103.8(4) . . ?
N1 C1 Mn1 125.6(4) . . ?
N2 C1 Mn1 130.6(4) . . ?
C1 N1 C2 111.4(4) . . ?
C1 N1 C4 125.2(4) . . ?
C2 N1 C4 123.4(4) . . ?
C3 C2 N1 107.1(4) . . ?
C3 C2 H2 126.5 . . ?
N1 C2 H2 126.5 . . ?
C2 C3 N2 106.5(5) . . ?
C2 C3 H3 126.8 . . ?
N2 C3 H3 126.8 . . ?
C1 N2 C3 111.3(4) . . ?
C1 N2 C12 125.6(4) . . ?
C3 N2 C12 122.8(4) . . ?
N1 C4 C5 112.0(4) . . ?
N1 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
N1 C4 H4B 109.2 . . ?
C5 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C4 C5 S1 115.6(4) . . ?
C4 C5 H5A 108.4 . . ?
S1 C5 H5A 108.4 . . ?
C4 C5 H5B 108.4 . . ?
S1 C5 H5B 108.4 . . ?
H5A C5 H5B 107.4 . . ?
C6 S1 C5 102.9(3) . . ?
C6 S1 Mn1 108.6(2) . . ?
C5 S1 Mn1 109.95(19) . . ?
C7 C6 C11 119.7(6) . . ?
C7 C6 S1 124.4(4) . . ?
C11 C6 S1 115.9(4) . . ?
C8 C7 C6 119.4(6) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C9 120.7(6) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 120.1(6) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 119.5(6) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C10 C11 C6 120.6(6) . . ?
C10 C11 H11 119.7 . . ?
C6 C11 H11 119.7 . . ?
N2 C12 C13 112.1(4) . . ?
N2 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
N2 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C18 119.0(5) . . ?
C14 C13 C12 120.4(5) . . ?
C18 C13 C12 120.6(5) . . ?
C13 C14 C15 120.4(6) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 119.1(6) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C17 120.8(6) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C16 C17 C18 120.0(6) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C13 120.6(6) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
O1 C19 Mn1 177.4(5) . . ?
O2 C20 Mn1 176.1(6) . . ?
O3 C21 Mn1 174.6(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
N2 C1 N1 C2 0.5(6) . . . . ?
Mn1 C1 N1 C2 -177.2(4) . . . . ?
N2 C1 N1 C4 -177.4(5) . . . . ?
Mn1 C1 N1 C4 5.0(7) . . . . ?
C1 N1 C2 C3 -0.2(7) . . . . ?
C4 N1 C2 C3 177.7(5) . . . . ?
N1 C2 C3 N2 -0.2(7) . . . . ?
N1 C1 N2 C3 -0.6(6) . . . . ?
Mn1 C1 N2 C3 176.8(4) . . . . ?
N1 C1 N2 C12 -174.3(5) . . . . ?
Mn1 C1 N2 C12 3.1(8) . . . . ?
C2 C3 N2 C1 0.5(7) . . . . ?
C2 C3 N2 C12 174.5(5) . . . . ?
C1 N1 C4 C5 60.6(7) . . . . ?
C2 N1 C4 C5 -117.0(6) . . . . ?
N1 C4 C5 S1 -62.6(5) . . . . ?
C4 C5 S1 C6 -102.6(4) . . . . ?
C4 C5 S1 Mn1 12.9(4) . . . . ?
C5 S1 C6 C7 26.8(6) . . . . ?
Mn1 S1 C6 C7 -89.7(5) . . . . ?
C5 S1 C6 C11 -153.8(5) . . . . ?
Mn1 S1 C6 C11 89.8(5) . . . . ?
C11 C6 C7 C8 0.6(10) . . . . ?
S1 C6 C7 C8 180.0(5) . . . . ?
C6 C7 C8 C9 0.4(11) . . . . ?
C7 C8 C9 C10 -1.4(13) . . . . ?
C8 C9 C10 C11 1.3(13) . . . . ?
C9 C10 C11 C6 -0.3(13) . . . . ?
C7 C6 C11 C10 -0.6(11) . . . . ?
S1 C6 C11 C10 179.9(6) . . . . ?
C1 N2 C12 C13 -148.9(5) . . . . ?
C3 N2 C12 C13 38.1(7) . . . . ?
N2 C12 C13 C14 65.0(6) . . . . ?
N2 C12 C13 C18 -116.5(5) . . . . ?
C18 C13 C14 C15 0.6(8) . . . . ?
C12 C13 C14 C15 179.1(5) . . . . ?
C13 C14 C15 C16 0.3(9) . . . . ?
C14 C15 C16 C17 -0.9(10) . . . . ?
C15 C16 C17 C18 0.4(10) . . . . ?
C16 C17 C18 C13 0.6(10) . . . . ?
C14 C13 C18 C17 -1.1(9) . . . . ?
C12 C13 C18 C17 -179.6(5) . . . . ?

_refine_diff_density_max         1.796
_refine_diff_density_min         -1.243
_refine_diff_density_rms         0.152




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

data_mcmh230615
_database_code_depnum_ccdc_archive 'CCDC 2406905'
loop_
_audit_author_name
_audit_author_address
'Nathalie GRUBER'
;University of Strasbourg
France
;
_audit_update_record             
;
2024-12-02 deposited with the CCDC.	2025-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H22 Br Mn N2 O3 S'
_chemical_formula_sum            'C23 H22 Br Mn N2 O3 S'
_chemical_formula_weight         541.33

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   8.4010(3)
_cell_length_b                   15.8222(7)
_cell_length_c                   16.6388(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2211.67(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9926
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      27.94

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_F_000             1096
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    2.526
_shelx_estimated_absorpt_T_min   0.719
_shelx_estimated_absorpt_T_max   0.823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6924
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Mo-ImuS 3.0 microfocus tube'
_diffrn_measurement_device_type  'Bruker PHOTON-III CPAD'
_diffrn_measurement_method       'φ and ω shuterless scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39013
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.448
_diffrn_reflns_theta_max         28.036
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5340
_reflns_number_gt                4743
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.997

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/3(Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0295P)²+0.7612P] 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_abs_structure_details 
;
 Flack x determined using 1897 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.027(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5340
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0693
_refine_ls_wR_factor_gt          0.0661
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5755(4) 0.4918(2) 0.4450(2) 0.0174(7) Uani 1 1 d . . . . .
C2 C 0.8071(5) 0.4733(3) 0.3768(3) 0.0274(9) Uani 1 1 d . . . . .
H2 H 0.887198 0.479704 0.336986 0.033 Uiso 1 1 calc R U . . .
C3 C 0.8125(5) 0.4220(3) 0.4403(3) 0.0291(9) Uani 1 1 d . . . . .
H3 H 0.897388 0.385371 0.454757 0.035 Uiso 1 1 calc R U . . .
C4 C 0.6155(4) 0.5737(2) 0.3182(2) 0.0179(7) Uani 1 1 d . . . . .
C5 C 0.6671(5) 0.6581(2) 0.3225(2) 0.0215(8) Uani 1 1 d . . . . .
C6 C 0.6172(5) 0.7121(2) 0.2615(2) 0.0222(8) Uani 1 1 d . . . . .
H6 H 0.648132 0.769805 0.263760 0.027 Uiso 1 1 calc R U . . .
C7 C 0.5244(5) 0.6852(2) 0.1978(2) 0.0207(8) Uani 1 1 d . . . . .
C8 C 0.4814(5) 0.6002(2) 0.1944(2) 0.0198(8) Uani 1 1 d . . . . .
H8 H 0.419634 0.580647 0.150294 0.024 Uiso 1 1 calc R U . . .
C9 C 0.5268(4) 0.5433(2) 0.2541(2) 0.0178(7) Uani 1 1 d . . . . .
C10 C 0.7767(5) 0.6885(3) 0.3877(3) 0.0321(10) Uani 1 1 d . . . . .
H10A H 0.887058 0.675830 0.373013 0.048 Uiso 1 1 calc R U . . .
H10B H 0.750343 0.659911 0.438256 0.048 Uiso 1 1 calc R U . . .
H10C H 0.764125 0.749704 0.394536 0.048 Uiso 1 1 calc R U . . .
C11 C 0.4718(6) 0.7464(2) 0.1338(3) 0.0279(9) Uani 1 1 d . . . . .
H11A H 0.393091 0.785499 0.156242 0.042 Uiso 1 1 calc R U . . .
H11B H 0.424125 0.715095 0.088989 0.042 Uiso 1 1 calc R U . . .
H11C H 0.564026 0.778354 0.114338 0.042 Uiso 1 1 calc R U . . .
C12 C 0.4826(5) 0.4514(2) 0.2485(2) 0.0229(8) Uani 1 1 d . . . . .
H12A H 0.578833 0.417632 0.239639 0.034 Uiso 1 1 calc R U . . .
H12B H 0.408955 0.443106 0.203485 0.034 Uiso 1 1 calc R U . . .
H12C H 0.431346 0.433650 0.298574 0.034 Uiso 1 1 calc R U . . .
C13 C 0.6330(5) 0.3873(3) 0.5555(2) 0.0266(8) Uani 1 1 d . . . . .
H13A H 0.716143 0.344211 0.565655 0.032 Uiso 1 1 calc R U . . .
H13B H 0.529996 0.357599 0.549275 0.032 Uiso 1 1 calc R U . . .
C14 C 0.6236(6) 0.4463(3) 0.6263(3) 0.0324(10) Uani 1 1 d . . . . .
H14A H 0.718669 0.483241 0.626974 0.039 Uiso 1 1 calc R U . . .
H14B H 0.623065 0.412947 0.676708 0.039 Uiso 1 1 calc R U . . .
C15 C 0.5154(4) 0.6051(2) 0.6703(2) 0.0208(8) Uani 1 1 d . . . . .
C16 C 0.4415(5) 0.6300(2) 0.7407(2) 0.0232(8) Uani 1 1 d . . . . .
H16 H 0.355565 0.597867 0.761688 0.028 Uiso 1 1 calc R U . . .
C17 C 0.4932(5) 0.7025(3) 0.7811(3) 0.0272(9) Uani 1 1 d . . . . .
H17 H 0.442539 0.719670 0.829420 0.033 Uiso 1 1 calc R U . . .
C18 C 0.6177(5) 0.7488(3) 0.7504(3) 0.0311(10) Uani 1 1 d . . . . .
H18 H 0.652053 0.798393 0.777465 0.037 Uiso 1 1 calc R U . . .
C19 C 0.6934(5) 0.7239(3) 0.6806(3) 0.0276(9) Uani 1 1 d . . . . .
H19 H 0.780031 0.756099 0.660345 0.033 Uiso 1 1 calc R U . . .
C20 C 0.6434(5) 0.6520(3) 0.6400(3) 0.0272(9) Uani 1 1 d . . . . .
H20 H 0.695570 0.634757 0.592105 0.033 Uiso 1 1 calc R U . . .
C21 C 0.2656(5) 0.5488(2) 0.3887(2) 0.0191(7) Uani 1 1 d . . . . .
C22 C 0.4236(5) 0.6448(2) 0.4815(3) 0.0229(7) Uani 1 1 d . . . . .
C23 C 0.1656(5) 0.5698(2) 0.5266(2) 0.0255(8) Uani 1 1 d . . . . .
N1 N 0.6632(4) 0.51523(19) 0.3798(2) 0.0186(6) Uani 1 1 d . . . . .
N2 N 0.6702(4) 0.43267(19) 0.4813(2) 0.0223(6) Uani 1 1 d . . . . .
O1 O 0.1923(3) 0.55775(17) 0.33133(17) 0.0242(6) Uani 1 1 d . . . . .
O2 O 0.4560(4) 0.71484(17) 0.47611(19) 0.0292(6) Uani 1 1 d . . . . .
O3 O 0.0439(4) 0.5899(2) 0.54797(19) 0.0354(8) Uani 1 1 d . . . . .
S1 S 0.44388(12) 0.51148(6) 0.62161(6) 0.0215(2) Uani 1 1 d . . . . .
Mn1 Mn 0.35949(6) 0.53686(3) 0.48559(4) 0.01744(12) Uani 1 1 d . . . . .
Br1 Br 0.24660(5) 0.38770(2) 0.48258(3) 0.02750(10) 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 1.362(5) . ?
C1 N2 1.369(5) . ?
C1 Mn1 2.064(4) . ?
C2 C3 1.333(6) . ?
C2 N1 1.380(4) . ?
C2 H2 0.9500 . ?
C3 N2 1.386(5) . ?
C3 H3 0.9500 . ?
C4 C9 1.388(5) . ?
C4 C5 1.407(5) . ?
C4 N1 1.438(5) . ?
C5 C6 1.390(6) . ?
C5 C10 1.502(6) . ?
C6 C7 1.383(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.394(5) . ?
C7 C11 1.506(5) . ?
C8 C9 1.395(5) . ?
C8 H8 0.9500 . ?
C9 C12 1.503(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 N2 1.463(5) . ?
C13 C14 1.505(6) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 S1 1.831(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.383(6) . ?
C15 C20 1.401(6) . ?
C15 S1 1.791(4) . ?
C16 C17 1.397(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.376(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.381(7) . ?
C18 H18 0.9500 . ?
C19 C20 1.388(6) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 O1 1.146(5) . ?
C21 Mn1 1.804(4) . ?
C22 O2 1.145(5) . ?
C22 Mn1 1.792(4) . ?
C23 O3 1.129(5) . ?
C23 Mn1 1.841(4) . ?
S1 Mn1 2.4054(11) . ?
Mn1 Br1 2.5440(6) . ?

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 N2 102.9(3) . . ?
N1 C1 Mn1 130.0(3) . . ?
N2 C1 Mn1 127.1(3) . . ?
C3 C2 N1 107.1(4) . . ?
C3 C2 H2 126.5 . . ?
N1 C2 H2 126.5 . . ?
C2 C3 N2 106.7(4) . . ?
C2 C3 H3 126.7 . . ?
N2 C3 H3 126.7 . . ?
C9 C4 C5 122.3(4) . . ?
C9 C4 N1 118.4(3) . . ?
C5 C4 N1 119.2(3) . . ?
C6 C5 C4 116.9(4) . . ?
C6 C5 C10 121.0(3) . . ?
C4 C5 C10 122.0(4) . . ?
C7 C6 C5 122.7(3) . . ?
C7 C6 H6 118.6 . . ?
C5 C6 H6 118.6 . . ?
C6 C7 C8 118.3(4) . . ?
C6 C7 C11 120.7(3) . . ?
C8 C7 C11 121.0(4) . . ?
C7 C8 C9 121.5(4) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C4 C9 C8 118.1(3) . . ?
C4 C9 C12 121.0(3) . . ?
C8 C9 C12 120.9(3) . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C14 111.6(3) . . ?
N2 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
N2 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 S1 111.0(3) . . ?
C13 C14 H14A 109.4 . . ?
S1 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
S1 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 C20 119.8(4) . . ?
C16 C15 S1 118.0(3) . . ?
C20 C15 S1 122.2(3) . . ?
C15 C16 C17 120.1(4) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 119.6(4) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 120.7(4) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C18 C19 C20 120.2(4) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C15 119.5(4) . . ?
C19 C20 H20 120.3 . . ?
C15 C20 H20 120.3 . . ?
O1 C21 Mn1 173.2(3) . . ?
O2 C22 Mn1 175.6(4) . . ?
O3 C23 Mn1 176.5(4) . . ?
C1 N1 C2 111.8(3) . . ?
C1 N1 C4 126.3(3) . . ?
C2 N1 C4 121.9(3) . . ?
C1 N2 C3 111.5(3) . . ?
C1 N2 C13 125.8(3) . . ?
C3 N2 C13 122.7(3) . . ?
C15 S1 C14 99.79(19) . . ?
C15 S1 Mn1 112.71(13) . . ?
C14 S1 Mn1 112.19(14) . . ?
C22 Mn1 C21 89.88(17) . . ?
C22 Mn1 C23 90.59(17) . . ?
C21 Mn1 C23 85.14(18) . . ?
C22 Mn1 C1 93.02(16) . . ?
C21 Mn1 C1 97.35(16) . . ?
C23 Mn1 C1 175.62(16) . . ?
C22 Mn1 S1 96.08(14) . . ?
C21 Mn1 S1 170.69(13) . . ?
C23 Mn1 S1 87.64(13) . . ?
C1 Mn1 S1 89.50(11) . . ?
C22 Mn1 Br1 174.52(13) . . ?
C21 Mn1 Br1 85.23(11) . . ?
C23 Mn1 Br1 86.56(12) . . ?
C1 Mn1 Br1 90.04(10) . . ?
S1 Mn1 Br1 88.48(3) . . ?

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 C2 C3 N2 0.6(5) . . . . ?
C9 C4 C5 C6 3.8(6) . . . . ?
N1 C4 C5 C6 -179.8(3) . . . . ?
C9 C4 C5 C10 -173.7(4) . . . . ?
N1 C4 C5 C10 2.7(6) . . . . ?
C4 C5 C6 C7 -1.6(6) . . . . ?
C10 C5 C6 C7 175.9(4) . . . . ?
C5 C6 C7 C8 -0.9(6) . . . . ?
C5 C6 C7 C11 179.3(4) . . . . ?
C6 C7 C8 C9 1.4(6) . . . . ?
C11 C7 C8 C9 -178.8(4) . . . . ?
C5 C4 C9 C8 -3.4(5) . . . . ?
N1 C4 C9 C8 -179.8(3) . . . . ?
C5 C4 C9 C12 175.9(4) . . . . ?
N1 C4 C9 C12 -0.5(5) . . . . ?
C7 C8 C9 C4 0.7(5) . . . . ?
C7 C8 C9 C12 -178.6(4) . . . . ?
N2 C13 C14 S1 72.0(4) . . . . ?
C20 C15 C16 C17 0.8(6) . . . . ?
S1 C15 C16 C17 179.8(3) . . . . ?
C15 C16 C17 C18 0.0(6) . . . . ?
C16 C17 C18 C19 -0.7(6) . . . . ?
C17 C18 C19 C20 0.7(6) . . . . ?
C18 C19 C20 C15 0.2(6) . . . . ?
C16 C15 C20 C19 -0.9(6) . . . . ?
S1 C15 C20 C19 -179.9(3) . . . . ?
N2 C1 N1 C2 -0.9(4) . . . . ?
Mn1 C1 N1 C2 175.8(3) . . . . ?
N2 C1 N1 C4 176.8(3) . . . . ?
Mn1 C1 N1 C4 -6.5(5) . . . . ?
C3 C2 N1 C1 0.2(5) . . . . ?
C3 C2 N1 C4 -177.6(4) . . . . ?
C9 C4 N1 C1 -85.6(5) . . . . ?
C5 C4 N1 C1 97.9(4) . . . . ?
C9 C4 N1 C2 91.9(4) . . . . ?
C5 C4 N1 C2 -84.6(5) . . . . ?
N1 C1 N2 C3 1.3(4) . . . . ?
Mn1 C1 N2 C3 -175.5(3) . . . . ?
N1 C1 N2 C13 179.2(3) . . . . ?
Mn1 C1 N2 C13 2.4(5) . . . . ?
C2 C3 N2 C1 -1.2(5) . . . . ?
C2 C3 N2 C13 -179.2(4) . . . . ?
C14 C13 N2 C1 -64.6(5) . . . . ?
C14 C13 N2 C3 113.1(4) . . . . ?
C16 C15 S1 C14 -118.5(3) . . . . ?
C20 C15 S1 C14 60.6(4) . . . . ?
C16 C15 S1 Mn1 122.4(3) . . . . ?
C20 C15 S1 Mn1 -58.6(4) . . . . ?
C13 C14 S1 C15 -148.9(3) . . . . ?
C13 C14 S1 Mn1 -29.4(4) . . . . ?

_refine_diff_density_max         0.361
_refine_diff_density_min         -0.621
_refine_diff_density_rms         0.070



