# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_bzlse
_database_code_depnum_ccdc_archive 'CCDC 1894674'
loop_
_audit_author_name
_audit_author_address
'Renata da Silva Heying'
;Universidade Federal de Santa Catarina
Brazil
;
_audit_update_record             
;
2019-01-30 deposited with the CCDC.	2019-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H23 Br Mn N O3 Se2'
_chemical_formula_sum            'C21 H23 Br Mn N O3 Se2'
_chemical_formula_weight         630.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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      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                   7.5601(2)
_cell_length_b                   12.4079(4)
_cell_length_c                   13.3682(5)
_cell_angle_alpha                103.0160(10)
_cell_angle_beta                 97.6530(10)
_cell_angle_gamma                104.8100(10)
_cell_volume                     1156.72(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9945
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      30.52

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.809
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    5.466
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4438
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   
;
Bruker APEX2, SAINT and SADABS, version 2011.8-0; Bruker AXS Inc., 
Madison, Wisconsin, USA
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(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            21399
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.597
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5046
_reflns_number_gt                4234
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0001P)²+6.5682P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5046
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.0968
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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 0.04822(8) 0.24717(6) 0.36963(5) 0.02279(15) Uani 1 1 d . . . . .
C1 C -0.0773(6) 0.2314(4) 0.2389(4) 0.0284(10) Uani 1 1 d . . . . .
C2 C -0.0982(6) 0.3315(4) 0.4210(4) 0.0288(10) Uani 1 1 d . . . . .
C3 C 0.2231(6) 0.3737(4) 0.3665(4) 0.0305(10) Uani 1 1 d . . . . .
Br1 Br -0.18077(6) 0.06458(4) 0.38307(4) 0.03612(13) Uani 1 1 d . . . . .
O1 O -0.1593(5) 0.2241(3) 0.1584(3) 0.0423(9) Uani 1 1 d . . . . .
O2 O -0.1944(5) 0.3841(3) 0.4491(3) 0.0448(9) Uani 1 1 d . . . . .
O3 O 0.3336(5) 0.4552(3) 0.3659(3) 0.0393(8) Uani 1 1 d . . . . .
N1 N 0.1941(5) 0.2525(3) 0.5191(3) 0.0284(8) Uani 1 1 d . . . . .
H1 H 0.121825 0.196548 0.533807 0.034 Uiso 1 1 d R U . . .
Se2 Se 0.25871(8) 0.48069(5) 0.82120(4) 0.04820(17) Uani 1 1 d . . . . .
Se1 Se 0.21551(6) 0.11019(4) 0.29952(4) 0.02842(12) Uani 1 1 d . . . . .
C4 C 0.2158(7) 0.3576(4) 0.6055(4) 0.0330(11) Uani 1 1 d . . . . .
H4A H 0.098658 0.379549 0.597570 0.040 Uiso 1 1 calc R U . . .
H4B H 0.316812 0.422155 0.597869 0.040 Uiso 1 1 calc R U . . .
C5 C 0.2605(7) 0.3437(5) 0.7159(4) 0.0407(12) Uani 1 1 d . . . . .
H5A H 0.385030 0.331359 0.728039 0.049 Uiso 1 1 calc R U . . .
H5B H 0.166997 0.274835 0.722533 0.049 Uiso 1 1 calc R U . . .
C6 C 0.3770(7) 0.2295(5) 0.5155(4) 0.0374(12) Uani 1 1 d . . . . .
H6A H 0.433113 0.226067 0.585522 0.045 Uiso 1 1 calc R U . . .
H6B H 0.462773 0.293670 0.497251 0.045 Uiso 1 1 calc R U . . .
C7 C 0.3546(7) 0.1176(5) 0.4362(4) 0.0366(11) Uani 1 1 d . . . . .
H7A H 0.287964 0.052302 0.461225 0.044 Uiso 1 1 calc R U . . .
H7B H 0.479482 0.109483 0.428991 0.044 Uiso 1 1 calc R U . . .
C10 C -0.0052(8) 0.4740(4) 0.7851(4) 0.0412(12) Uani 1 1 d . . . . .
H10A H -0.023293 0.544593 0.828843 0.049 Uiso 1 1 calc R U . . .
H10B H -0.033525 0.475383 0.711019 0.049 Uiso 1 1 calc R U . . .
C11 C -0.1429(7) 0.3704(4) 0.7991(4) 0.0304(10) Uani 1 1 d . . . . .
C12 C -0.2068(8) 0.3747(5) 0.8920(4) 0.0464(14) Uani 1 1 d . . . . .
H12 H -0.162310 0.444291 0.947289 0.056 Uiso 1 1 calc R U . . .
C13 C -0.3340(9) 0.2798(6) 0.9057(5) 0.0576(17) Uani 1 1 d . . . . .
H13 H -0.375038 0.284117 0.970223 0.069 Uiso 1 1 calc R U . . .
C14 C -0.4010(8) 0.1789(5) 0.8257(6) 0.0559(17) Uani 1 1 d . . . . .
H14 H -0.488658 0.113413 0.834662 0.067 Uiso 1 1 calc R U . . .
C15 C -0.3404(8) 0.1737(5) 0.7335(5) 0.0493(15) Uani 1 1 d . . . . .
H15 H -0.386308 0.103871 0.678453 0.059 Uiso 1 1 calc R U . . .
C16 C -0.2133(7) 0.2681(4) 0.7185(4) 0.0387(12) Uani 1 1 d . . . . .
H16 H -0.174180 0.263172 0.653429 0.046 Uiso 1 1 calc R U . . .
C20 C 0.4212(6) 0.1861(5) 0.2374(4) 0.0368(11) Uani 1 1 d . . . . .
H20A H 0.480844 0.267456 0.279039 0.044 Uiso 1 1 calc R U . . .
H20B H 0.517296 0.144815 0.235938 0.044 Uiso 1 1 calc R U . . .
C21 C 0.3352(6) 0.1813(4) 0.1280(4) 0.0338(11) Uani 1 1 d . . . . .
C22 C 0.2916(8) 0.2763(5) 0.1057(4) 0.0426(13) Uani 1 1 d . . . . .
H22 H 0.323925 0.346996 0.159200 0.051 Uiso 1 1 calc R U . . .
C23 C 0.2014(9) 0.2694(6) 0.0063(5) 0.0545(16) Uani 1 1 d . . . . .
H23 H 0.173404 0.335475 -0.007948 0.065 Uiso 1 1 calc R U . . .
C24 C 0.1526(9) 0.1690(6) -0.0707(5) 0.0599(18) Uani 1 1 d . . . . .
H24 H 0.087502 0.163981 -0.138236 0.072 Uiso 1 1 calc R U . . .
C25 C 0.1977(11) 0.0746(6) -0.0507(5) 0.068(2) Uani 1 1 d . . . . .
H25 H 0.166989 0.004904 -0.105301 0.082 Uiso 1 1 calc R U . . .
C26 C 0.2868(10) 0.0801(5) 0.0476(4) 0.0513(15) Uani 1 1 d . . . . .
H26 H 0.315591 0.013741 0.060573 0.062 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 C3 1.788(5) . ?
Mn1 C2 1.806(5) . ?
Mn1 C1 1.817(5) . ?
Mn1 N1 2.129(4) . ?
Mn1 Se1 2.4625(8) . ?
Mn1 Br1 2.5344(8) . ?
C1 O1 1.140(6) . ?
C2 O2 1.141(6) . ?
C3 O3 1.138(6) . ?
N1 C6 1.486(6) . ?
N1 C4 1.491(6) . ?
N1 H1 0.8455 . ?
Se2 C5 1.952(6) . ?
Se2 C10 1.965(6) . ?
Se1 C7 1.954(5) . ?
Se1 C20 1.986(5) . ?
C4 C5 1.528(7) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.499(7) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C10 C11 1.498(7) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.386(7) . ?
C11 C16 1.393(7) . ?
C12 C13 1.383(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.377(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.366(9) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(8) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C20 C21 1.501(7) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.385(7) . ?
C21 C26 1.385(8) . ?
C22 C23 1.383(8) . ?
C22 H22 0.9500 . ?
C23 C24 1.354(9) . ?
C23 H23 0.9500 . ?
C24 C25 1.370(10) . ?
C24 H24 0.9500 . ?
C25 C26 1.373(9) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 Mn1 C2 92.1(2) . . ?
C3 Mn1 C1 92.2(2) . . ?
C2 Mn1 C1 88.0(2) . . ?
C3 Mn1 N1 90.56(19) . . ?
C2 Mn1 N1 95.13(18) . . ?
C1 Mn1 N1 175.76(18) . . ?
C3 Mn1 Se1 95.26(15) . . ?
C2 Mn1 Se1 172.65(15) . . ?
C1 Mn1 Se1 91.44(15) . . ?
N1 Mn1 Se1 85.11(11) . . ?
C3 Mn1 Br1 175.63(16) . . ?
C2 Mn1 Br1 90.21(15) . . ?
C1 Mn1 Br1 91.59(14) . . ?
N1 Mn1 Br1 85.54(11) . . ?
Se1 Mn1 Br1 82.47(3) . . ?
O1 C1 Mn1 177.6(4) . . ?
O2 C2 Mn1 177.1(4) . . ?
O3 C3 Mn1 178.9(5) . . ?
C6 N1 C4 110.5(4) . . ?
C6 N1 Mn1 112.9(3) . . ?
C4 N1 Mn1 115.9(3) . . ?
C6 N1 H1 108.4 . . ?
C4 N1 H1 106.3 . . ?
Mn1 N1 H1 102.0 . . ?
C5 Se2 C10 99.9(2) . . ?
C7 Se1 C20 100.7(2) . . ?
C7 Se1 Mn1 95.12(15) . . ?
C20 Se1 Mn1 110.73(16) . . ?
N1 C4 C5 114.8(4) . . ?
N1 C4 H4A 108.6 . . ?
C5 C4 H4A 108.6 . . ?
N1 C4 H4B 108.6 . . ?
C5 C4 H4B 108.6 . . ?
H4A C4 H4B 107.5 . . ?
C4 C5 Se2 110.8(4) . . ?
C4 C5 H5A 109.5 . . ?
Se2 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
Se2 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
N1 C6 C7 111.1(4) . . ?
N1 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
N1 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 Se1 111.7(3) . . ?
C6 C7 H7A 109.3 . . ?
Se1 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
Se1 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C11 C10 Se2 115.4(4) . . ?
C11 C10 H10A 108.4 . . ?
Se2 C10 H10A 108.4 . . ?
C11 C10 H10B 108.4 . . ?
Se2 C10 H10B 108.4 . . ?
H10A C10 H10B 107.5 . . ?
C12 C11 C16 118.1(5) . . ?
C12 C11 C10 120.8(5) . . ?
C16 C11 C10 121.1(5) . . ?
C13 C12 C11 121.3(6) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C14 C13 C12 119.9(6) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 119.4(6) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 121.3(6) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C11 119.9(5) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
C21 C20 Se1 106.8(3) . . ?
C21 C20 H20A 110.4 . . ?
Se1 C20 H20A 110.4 . . ?
C21 C20 H20B 110.4 . . ?
Se1 C20 H20B 110.4 . . ?
H20A C20 H20B 108.6 . . ?
C22 C21 C26 117.8(5) . . ?
C22 C21 C20 120.8(5) . . ?
C26 C21 C20 121.2(5) . . ?
C23 C22 C21 120.7(6) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C24 C23 C22 120.4(6) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 119.7(6) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C24 C25 C26 120.5(6) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 120.8(6) . . ?
C25 C26 H26 119.6 . . ?
C21 C26 H26 119.6 . . ?

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
C6 N1 C4 C5 -69.2(5) . . . . ?
Mn1 N1 C4 C5 160.8(3) . . . . ?
N1 C4 C5 Se2 -173.9(3) . . . . ?
C4 N1 C6 C7 174.3(4) . . . . ?
Mn1 N1 C6 C7 -54.1(5) . . . . ?
N1 C6 C7 Se1 51.8(5) . . . . ?
Se2 C10 C11 C12 92.9(5) . . . . ?
Se2 C10 C11 C16 -88.5(5) . . . . ?
C16 C11 C12 C13 1.3(8) . . . . ?
C10 C11 C12 C13 179.9(5) . . . . ?
C11 C12 C13 C14 -0.7(10) . . . . ?
C12 C13 C14 C15 0.2(10) . . . . ?
C13 C14 C15 C16 -0.3(9) . . . . ?
C14 C15 C16 C11 0.9(8) . . . . ?
C12 C11 C16 C15 -1.4(7) . . . . ?
C10 C11 C16 C15 180.0(5) . . . . ?
Se1 C20 C21 C22 99.1(5) . . . . ?
Se1 C20 C21 C26 -77.0(5) . . . . ?
C26 C21 C22 C23 0.4(8) . . . . ?
C20 C21 C22 C23 -175.8(5) . . . . ?
C21 C22 C23 C24 0.6(9) . . . . ?
C22 C23 C24 C25 -1.8(10) . . . . ?
C23 C24 C25 C26 2.0(11) . . . . ?
C24 C25 C26 C21 -0.9(11) . . . . ?
C22 C21 C26 C25 -0.3(9) . . . . ?
C20 C21 C26 C25 175.9(6) . . . . ?

_refine_diff_density_max         1.696
_refine_diff_density_min         -0.763
_refine_diff_density_rms         0.122

####################################################################### 
# 
# 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_phse
_database_code_depnum_ccdc_archive 'CCDC 1894677'
loop_
_audit_author_name
_audit_author_address
'Renata da Silva Heying'
;Universidade Federal de Santa Catarina
Brazil
;
_audit_update_record             
;
2019-01-30 deposited with the CCDC.	2019-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H19 Br Mn N O3 Se2'
_chemical_formula_sum            'C19 H19 Br Mn N O3 Se2'
_chemical_formula_weight         602.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.0565(2)
_cell_length_b                   20.5626(5)
_cell_length_c                   12.9929(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.4920(10)
_cell_angle_gamma                90
_cell_volume                     2145.83(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    8912
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      30.52

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.864
_exptl_crystal_F_000             1168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    5.888
_shelx_estimated_absorpt_T_min   0.226
_shelx_estimated_absorpt_T_max   0.799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3812
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
Bruker APEX2, SAINT and SADABS, version 2011.8-0; Bruker AXS Inc., 
Madison, Wisconsin, USA
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(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            18943
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.858
_diffrn_reflns_theta_max         27.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5183
_reflns_number_gt                4133
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0280P)²+4.3978P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5183
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.0881
_refine_ls_wR_factor_gt          0.0812
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.002
_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 0.42019(7) 0.67721(3) 0.59328(4) 0.02467(13) Uani 1 1 d . . . . .
C1 C 0.4557(5) 0.6106(2) 0.6826(3) 0.0400(10) Uani 1 1 d . . . . .
C2 C 0.6284(5) 0.7050(2) 0.6302(3) 0.0344(9) Uani 1 1 d . . . . .
C3 C 0.4947(5) 0.6293(2) 0.4915(3) 0.0317(8) Uani 1 1 d . . . . .
Br1 Br 0.31903(5) 0.74822(2) 0.73438(3) 0.03560(11) Uani 1 1 d . . . . .
O1 O 0.4817(5) 0.5679(2) 0.7381(3) 0.0681(11) Uani 1 1 d . . . . .
O2 O 0.7618(4) 0.72047(19) 0.6572(2) 0.0513(8) Uani 1 1 d . . . . .
O3 O 0.5490(4) 0.59841(16) 0.4287(2) 0.0482(8) Uani 1 1 d . . . . .
N1 N 0.3596(4) 0.75685(14) 0.4923(2) 0.0249(6) Uani 1 1 d . . . . .
H1 H 0.352984 0.787546 0.533611 0.030 Uiso 1 1 d R U . . .
Se2 Se 0.12144(4) 0.64833(2) 0.56806(3) 0.02499(9) Uani 1 1 d . . . . .
Se1 Se 0.46508(5) 0.91277(2) 0.47645(3) 0.03454(11) Uani 1 1 d . . . . .
C4 C 0.4896(5) 0.77569(19) 0.4227(3) 0.0296(8) Uani 1 1 d . . . . .
H4A H 0.490480 0.743174 0.366510 0.036 Uiso 1 1 calc R U . . .
H4B H 0.599582 0.773913 0.462324 0.036 Uiso 1 1 calc R U . . .
C5 C 0.4677(5) 0.84298(19) 0.3744(3) 0.0334(9) Uani 1 1 d . . . . .
H5A H 0.361980 0.843972 0.330185 0.040 Uiso 1 1 calc R U . . .
H5B H 0.559615 0.850983 0.329737 0.040 Uiso 1 1 calc R U . . .
C6 C 0.1942(5) 0.75158(19) 0.4323(3) 0.0291(8) Uani 1 1 d . . . . .
H6A H 0.201495 0.719662 0.375750 0.035 Uiso 1 1 calc R U . . .
H6B H 0.163782 0.794247 0.400876 0.035 Uiso 1 1 calc R U . . .
C7 C 0.0613(5) 0.73057(17) 0.5004(3) 0.0279(8) Uani 1 1 d . . . . .
H7A H -0.045824 0.725595 0.458355 0.033 Uiso 1 1 calc R U . . .
H7B H 0.046859 0.764345 0.553266 0.033 Uiso 1 1 calc R U . . .
C11 C 0.6922(5) 0.90496(18) 0.5301(3) 0.0320(8) Uani 1 1 d . . . . .
C12 C 0.7317(8) 0.8851(3) 0.6299(4) 0.0619(15) Uani 1 1 d . . . . .
H12 H 0.647279 0.873862 0.673801 0.074 Uiso 1 1 calc R U . . .
C13 C 0.9040(10) 0.8818(3) 0.6656(5) 0.084(2) Uani 1 1 d . . . . .
H13 H 0.935376 0.869050 0.734618 0.100 Uiso 1 1 calc R U . . .
C14 C 1.0232(8) 0.8970(3) 0.6008(6) 0.0711(18) Uani 1 1 d . . . . .
H14 H 1.137315 0.893949 0.625016 0.085 Uiso 1 1 calc R U . . .
C15 C 0.9825(7) 0.9163(3) 0.5035(5) 0.0659(15) Uani 1 1 d . . . . .
H15 H 1.067254 0.926754 0.459349 0.079 Uiso 1 1 calc R U . . .
C16 C 0.8187(6) 0.9208(3) 0.4679(4) 0.0520(12) Uani 1 1 d . . . . .
H16 H 0.790792 0.935057 0.399221 0.062 Uiso 1 1 calc R U . . .
C21 C 0.0856(5) 0.58900(17) 0.4531(3) 0.0267(7) Uani 1 1 d . . . . .
C22 C 0.1825(5) 0.53346(19) 0.4524(4) 0.0384(9) Uani 1 1 d . . . . .
H22 H 0.270007 0.526957 0.504697 0.046 Uiso 1 1 calc R U . . .
C23 C 0.1523(6) 0.4877(2) 0.3761(4) 0.0502(12) Uani 1 1 d . . . . .
H23 H 0.219124 0.449606 0.375843 0.060 Uiso 1 1 calc R U . . .
C24 C 0.0264(8) 0.4968(2) 0.3007(4) 0.0581(15) Uani 1 1 d . . . . .
H24 H 0.006770 0.465435 0.247482 0.070 Uiso 1 1 calc R U . . .
C25 C -0.0703(9) 0.5507(3) 0.3019(4) 0.0652(17) Uani 1 1 d . . . . .
H25 H -0.157743 0.556482 0.249358 0.078 Uiso 1 1 calc R U . . .
C26 C -0.0442(6) 0.5977(2) 0.3787(3) 0.0457(11) Uani 1 1 d . . . . .
H26 H -0.114032 0.634920 0.379702 0.055 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 C3 1.790(4) . ?
Mn1 C2 1.801(4) . ?
Mn1 C1 1.803(4) . ?
Mn1 N1 2.131(3) . ?
Mn1 Se2 2.4758(7) . ?
Mn1 Br1 2.5280(6) . ?
C1 O1 1.145(5) . ?
C2 O2 1.149(5) . ?
C3 O3 1.148(5) . ?
N1 C4 1.488(4) . ?
N1 C6 1.494(5) . ?
N1 H1 0.8334 . ?
Se2 C21 1.932(4) . ?
Se2 C7 1.949(4) . ?
Se1 C11 1.913(4) . ?
Se1 C5 1.955(4) . ?
C4 C5 1.523(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.505(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C11 C12 1.372(6) . ?
C11 C16 1.388(6) . ?
C12 C13 1.431(9) . ?
C12 H12 0.9500 . ?
C13 C14 1.362(10) . ?
C13 H13 0.9500 . ?
C14 C15 1.341(9) . ?
C14 H14 0.9500 . ?
C15 C16 1.367(7) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C26 1.379(6) . ?
C21 C22 1.384(5) . ?
C22 C23 1.374(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.367(8) . ?
C23 H23 0.9500 . ?
C24 C25 1.355(8) . ?
C24 H24 0.9500 . ?
C25 C26 1.394(6) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 Mn1 C2 90.70(18) . . ?
C3 Mn1 C1 90.73(18) . . ?
C2 Mn1 C1 88.39(19) . . ?
C3 Mn1 N1 92.36(14) . . ?
C2 Mn1 N1 94.81(15) . . ?
C1 Mn1 N1 175.52(16) . . ?
C3 Mn1 Se2 98.58(13) . . ?
C2 Mn1 Se2 170.66(12) . . ?
C1 Mn1 Se2 90.38(14) . . ?
N1 Mn1 Se2 85.96(8) . . ?
C3 Mn1 Br1 178.05(13) . . ?
C2 Mn1 Br1 88.27(13) . . ?
C1 Mn1 Br1 90.89(14) . . ?
N1 Mn1 Br1 86.08(8) . . ?
Se2 Mn1 Br1 82.49(2) . . ?
O1 C1 Mn1 178.3(4) . . ?
O2 C2 Mn1 176.8(4) . . ?
O3 C3 Mn1 177.0(4) . . ?
C4 N1 C6 110.1(3) . . ?
C4 N1 Mn1 115.9(2) . . ?
C6 N1 Mn1 114.7(2) . . ?
C4 N1 H1 106.2 . . ?
C6 N1 H1 107.0 . . ?
Mn1 N1 H1 102.0 . . ?
C21 Se2 C7 100.51(16) . . ?
C21 Se2 Mn1 109.80(11) . . ?
C7 Se2 Mn1 93.23(11) . . ?
C11 Se1 C5 97.16(17) . . ?
N1 C4 C5 115.0(3) . . ?
N1 C4 H4A 108.5 . . ?
C5 C4 H4A 108.5 . . ?
N1 C4 H4B 108.5 . . ?
C5 C4 H4B 108.5 . . ?
H4A C4 H4B 107.5 . . ?
C4 C5 Se1 113.3(2) . . ?
C4 C5 H5A 108.9 . . ?
Se1 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
Se1 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
N1 C6 C7 111.1(3) . . ?
N1 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
N1 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 Se2 110.6(2) . . ?
C6 C7 H7A 109.5 . . ?
Se2 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
Se2 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C12 C11 C16 119.5(5) . . ?
C12 C11 Se1 120.9(4) . . ?
C16 C11 Se1 119.5(3) . . ?
C11 C12 C13 117.9(6) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 H12 121.1 . . ?
C14 C13 C12 120.2(5) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 121.2(6) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 119.8(6) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C11 121.4(5) . . ?
C15 C16 H16 119.3 . . ?
C11 C16 H16 119.3 . . ?
C26 C21 C22 120.0(4) . . ?
C26 C21 Se2 121.3(3) . . ?
C22 C21 Se2 118.4(3) . . ?
C23 C22 C21 120.2(4) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C24 C23 C22 120.1(5) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C25 C24 C23 119.9(4) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 121.4(5) . . ?
C24 C25 H25 119.3 . . ?
C26 C25 H25 119.3 . . ?
C21 C26 C25 118.3(5) . . ?
C21 C26 H26 120.8 . . ?
C25 C26 H26 120.8 . . ?

_refine_diff_density_max         0.891
_refine_diff_density_min         -0.857
_refine_diff_density_rms         0.111

####################################################################### 
# 
# 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_phs
_database_code_depnum_ccdc_archive 'CCDC 1894675'
loop_
_audit_author_name
_audit_author_address
'Renata da Silva Heying'
;Universidade Federal de Santa Catarina
Brazil
;
_audit_update_record             
;
2019-01-30 deposited with the CCDC.	2019-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H19 Br Mn N O3 S2'
_chemical_formula_sum            'C19 H19 Br Mn N O3 S2'
_chemical_formula_weight         508.32

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

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

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

_cell_length_a                   7.9129(3)
_cell_length_b                   20.3755(8)
_cell_length_c                   13.0456(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.8700(10)
_cell_angle_gamma                90
_cell_volume                     2095.74(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    6051
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      27.34

_exptl_crystal_description       irregular
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.754
_shelx_estimated_absorpt_T_min   0.513
_shelx_estimated_absorpt_T_max   0.875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6390
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   
;
Bruker APEX2, SAINT and SADABS, version 2011.8-0; Bruker AXS Inc., 
Madison, Wisconsin, USA
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(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            27132
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.858
_diffrn_reflns_theta_max         31.163
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6757
_reflns_number_gt                4850
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0346P)²+1.2928P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6757
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.0884
_refine_ls_wR_factor_gt          0.0788
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.42001(4) 0.67521(2) 0.58591(3) 0.02345(8) Uani 1 1 d . . . . .
C1 C 0.4520(3) 0.60649(14) 0.6733(2) 0.0366(6) Uani 1 1 d . . . . .
C2 C 0.6327(3) 0.70193(13) 0.62625(19) 0.0329(5) Uani 1 1 d . . . . .
C3 C 0.4969(3) 0.62832(13) 0.48304(19) 0.0306(5) Uani 1 1 d . . . . .
O1 O 0.4748(3) 0.56275(12) 0.72751(18) 0.0626(7) Uani 1 1 d . . . . .
O2 O 0.7676(2) 0.71623(12) 0.65576(16) 0.0498(5) Uani 1 1 d . . . . .
O3 O 0.5542(3) 0.59834(11) 0.42052(15) 0.0474(5) Uani 1 1 d . . . . .
Br1 Br 0.31898(3) 0.74518(2) 0.72871(2) 0.03479(8) Uani 1 1 d . . . . .
N1 N 0.3618(2) 0.75694(9) 0.48800(14) 0.0235(4) Uani 1 1 d . . . . .
H1 H 0.354016 0.789212 0.531828 0.028 Uiso 1 1 d R U . . .
S2 S 0.12803(7) 0.64877(3) 0.55381(4) 0.02452(12) Uani 1 1 d . . . . .
S1 S 0.47964(8) 0.90908(3) 0.47093(6) 0.03742(16) Uani 1 1 d . . . . .
C4 C 0.4933(3) 0.77645(12) 0.41892(19) 0.0288(5) Uani 1 1 d . . . . .
H4A H 0.491834 0.744566 0.361582 0.035 Uiso 1 1 calc R U . . .
H4B H 0.605971 0.773528 0.457933 0.035 Uiso 1 1 calc R U . . .
C5 C 0.4722(3) 0.84495(12) 0.37406(19) 0.0330(5) Uani 1 1 d . . . . .
H5A H 0.362209 0.847439 0.332026 0.040 Uiso 1 1 calc R U . . .
H5B H 0.563097 0.852905 0.327870 0.040 Uiso 1 1 calc R U . . .
C6 C 0.1931(3) 0.75171(12) 0.42831(19) 0.0273(5) Uani 1 1 d . . . . .
H6A H 0.201201 0.721438 0.369569 0.033 Uiso 1 1 calc R U . . .
H6B H 0.158367 0.795348 0.400602 0.033 Uiso 1 1 calc R U . . .
C7 C 0.0621(3) 0.72658(11) 0.49616(19) 0.0272(5) Uani 1 1 d . . . . .
H7A H -0.047745 0.720991 0.454760 0.033 Uiso 1 1 calc R U . . .
H7B H 0.046001 0.759018 0.550997 0.033 Uiso 1 1 calc R U . . .
C11 C 0.6960(3) 0.90326(12) 0.5200(2) 0.0343(6) Uani 1 1 d . . . . .
C12 C 0.8220(4) 0.92004(16) 0.4583(3) 0.0517(8) Uani 1 1 d . . . . .
H12 H 0.792024 0.933838 0.389597 0.062 Uiso 1 1 calc R U . . .
C13 C 0.9902(4) 0.91724(19) 0.4941(4) 0.0701(11) Uani 1 1 d . . . . .
H13 H 1.075067 0.929136 0.450163 0.084 Uiso 1 1 calc R U . . .
C14 C 1.0345(5) 0.89798(19) 0.5896(4) 0.0758(13) Uani 1 1 d . . . . .
H14 H 1.151305 0.895709 0.613136 0.091 Uiso 1 1 calc R U . . .
C15 C 0.9157(6) 0.8814(2) 0.6546(3) 0.0873(14) Uani 1 1 d . . . . .
H15 H 0.949720 0.868483 0.723249 0.105 Uiso 1 1 calc R U . . .
C16 C 0.7399(5) 0.8834(2) 0.6195(3) 0.0666(10) Uani 1 1 d . . . . .
H16 H 0.655529 0.871317 0.663676 0.080 Uiso 1 1 calc R U . . .
C21 C 0.0946(3) 0.59130(11) 0.45018(18) 0.0263(5) Uani 1 1 d . . . . .
C22 C -0.0262(4) 0.60045(14) 0.3689(2) 0.0449(7) Uani 1 1 d . . . . .
H22 H -0.090403 0.639867 0.363176 0.054 Uiso 1 1 calc R U . . .
C23 C -0.0527(5) 0.55142(16) 0.2958(2) 0.0617(10) Uani 1 1 d . . . . .
H23 H -0.134875 0.557744 0.239282 0.074 Uiso 1 1 calc R U . . .
C24 C 0.0377(4) 0.49377(15) 0.3036(2) 0.0539(8) Uani 1 1 d . . . . .
H24 H 0.019462 0.460816 0.252308 0.065 Uiso 1 1 calc R U . . .
C25 C 0.1544(4) 0.48433(14) 0.3860(2) 0.0438(7) Uani 1 1 d . . . . .
H25 H 0.215476 0.444203 0.392571 0.053 Uiso 1 1 calc R U . . .
C26 C 0.1838(3) 0.53248(12) 0.4594(2) 0.0347(6) Uani 1 1 d . . . . .
H26 H 0.265037 0.525536 0.516269 0.042 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 C3 1.795(3) . ?
Mn1 C2 1.804(3) . ?
Mn1 C1 1.810(3) . ?
Mn1 N1 2.1255(19) . ?
Mn1 S2 2.3748(6) . ?
Mn1 Br1 2.5288(4) . ?
C1 O1 1.142(3) . ?
C2 O2 1.141(3) . ?
C3 O3 1.143(3) . ?
N1 C4 1.488(3) . ?
N1 C6 1.490(3) . ?
N1 H1 0.8770 . ?
S2 C21 1.791(2) . ?
S2 C7 1.812(2) . ?
S1 C11 1.780(3) . ?
S1 C5 1.815(3) . ?
C4 C5 1.517(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.509(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C11 C16 1.376(4) . ?
C11 C12 1.377(4) . ?
C12 C13 1.374(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.325(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.361(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.428(6) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C22 1.378(4) . ?
C21 C26 1.391(3) . ?
C22 C23 1.385(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.374(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.370(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.377(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 Mn1 C2 90.67(11) . . ?
C3 Mn1 C1 91.21(12) . . ?
C2 Mn1 C1 88.43(12) . . ?
C3 Mn1 N1 92.16(9) . . ?
C2 Mn1 N1 95.06(10) . . ?
C1 Mn1 N1 175.13(9) . . ?
C3 Mn1 S2 97.70(8) . . ?
C2 Mn1 S2 171.63(9) . . ?
C1 Mn1 S2 91.01(9) . . ?
N1 Mn1 S2 85.05(5) . . ?
C3 Mn1 Br1 177.65(8) . . ?
C2 Mn1 Br1 87.73(8) . . ?
C1 Mn1 Br1 90.47(9) . . ?
N1 Mn1 Br1 86.27(5) . . ?
S2 Mn1 Br1 83.918(18) . . ?
O1 C1 Mn1 178.7(2) . . ?
O2 C2 Mn1 176.3(2) . . ?
O3 C3 Mn1 176.3(2) . . ?
C4 N1 C6 110.13(18) . . ?
C4 N1 Mn1 116.50(14) . . ?
C6 N1 Mn1 113.38(13) . . ?
C4 N1 H1 106.6 . . ?
C6 N1 H1 106.6 . . ?
Mn1 N1 H1 102.7 . . ?
C21 S2 C7 103.88(11) . . ?
C21 S2 Mn1 111.12(8) . . ?
C7 S2 Mn1 96.68(7) . . ?
C11 S1 C5 100.12(12) . . ?
N1 C4 C5 114.8(2) . . ?
N1 C4 H4A 108.6 . . ?
C5 C4 H4A 108.6 . . ?
N1 C4 H4B 108.6 . . ?
C5 C4 H4B 108.6 . . ?
H4A C4 H4B 107.5 . . ?
C4 C5 S1 113.44(18) . . ?
C4 C5 H5A 108.9 . . ?
S1 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
S1 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
N1 C6 C7 110.32(19) . . ?
N1 C6 H6A 109.6 . . ?
C7 C6 H6A 109.6 . . ?
N1 C6 H6B 109.6 . . ?
C7 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C6 C7 S2 110.62(15) . . ?
C6 C7 H7A 109.5 . . ?
S2 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
S2 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C16 C11 C12 119.2(3) . . ?
C16 C11 S1 121.1(3) . . ?
C12 C11 S1 119.7(2) . . ?
C13 C12 C11 121.3(4) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C14 C13 C12 120.2(4) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 121.2(4) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C14 C15 C16 119.9(4) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C11 C16 C15 118.1(4) . . ?
C11 C16 H16 120.9 . . ?
C15 C16 H16 120.9 . . ?
C22 C21 C26 119.8(2) . . ?
C22 C21 S2 122.70(19) . . ?
C26 C21 S2 117.19(19) . . ?
C21 C22 C23 119.1(3) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C24 C23 C22 121.2(3) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C25 C24 C23 119.3(3) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C24 C25 C26 120.6(3) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C25 C26 C21 119.9(3) . . ?
C25 C26 H26 120.0 . . ?
C21 C26 H26 120.0 . . ?

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
C6 N1 C4 C5 66.2(3) . . . . ?
Mn1 N1 C4 C5 -162.93(16) . . . . ?
N1 C4 C5 S1 60.2(2) . . . . ?
C11 S1 C5 C4 67.8(2) . . . . ?
C4 N1 C6 C7 175.37(19) . . . . ?
Mn1 N1 C6 C7 42.8(2) . . . . ?
N1 C6 C7 S2 -56.1(2) . . . . ?
C21 S2 C7 C6 -74.64(18) . . . . ?
Mn1 S2 C7 C6 39.11(17) . . . . ?
C5 S1 C11 C16 -114.1(3) . . . . ?
C5 S1 C11 C12 67.1(2) . . . . ?
C16 C11 C12 C13 0.1(5) . . . . ?
S1 C11 C12 C13 178.9(3) . . . . ?
C11 C12 C13 C14 0.1(6) . . . . ?
C12 C13 C14 C15 -0.8(6) . . . . ?
C13 C14 C15 C16 1.2(7) . . . . ?
C12 C11 C16 C15 0.3(5) . . . . ?
S1 C11 C16 C15 -178.5(3) . . . . ?
C14 C15 C16 C11 -0.9(6) . . . . ?
C7 S2 C21 C22 -27.7(3) . . . . ?
Mn1 S2 C21 C22 -130.6(2) . . . . ?
C7 S2 C21 C26 158.99(19) . . . . ?
Mn1 S2 C21 C26 56.0(2) . . . . ?
C26 C21 C22 C23 -2.1(4) . . . . ?
S2 C21 C22 C23 -175.2(3) . . . . ?
C21 C22 C23 C24 0.8(5) . . . . ?
C22 C23 C24 C25 1.0(5) . . . . ?
C23 C24 C25 C26 -1.4(5) . . . . ?
C24 C25 C26 C21 0.0(4) . . . . ?
C22 C21 C26 C25 1.7(4) . . . . ?
S2 C21 C26 C25 175.2(2) . . . . ?

_refine_diff_density_max         0.584
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.086

