# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_KR1108_AhMa_a
_database_code_depnum_ccdc_archive 'CCDC 2180129'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Radacki'
;Institute of Inorganic Chemistry, Wuerzburg University, Am Hubland, Wuerzburg, Germany
Germany
;
_audit_update_record             
;
2022-06-18 deposited with the CCDC.	2022-09-02 downloaded from the CCDC.
;

_audit_creation_method           'CIF-fill 1.2z (K.Radacki, 2005-22)'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H8 Br Mn N2 O3'
_chemical_formula_sum            'C12 H8 Br Mn N2 O3'
_chemical_formula_weight         363.05

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'
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'
Mn Mn -0.5299 2.8052 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.39880(10)
_cell_length_b                   17.17570(10)
_cell_length_c                   12.32030(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.7500(10)
_cell_angle_gamma                90
_cell_volume                     2620.69(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9878
_cell_measurement_theta_min      4.3940
_cell_measurement_theta_max      72.8120


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide loop and transferred to stream of cold nitrogen (Oxford Cryostream 800).
;
_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.840
_exptl_crystal_F_000             1424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.289
_exptl_crystal_size_mid          0.241
_exptl_crystal_size_min          0.071
_exptl_absorpt_coefficient_mu    11.827
_shelx_estimated_absorpt_T_min   0.131
_shelx_estimated_absorpt_T_max   0.492
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.013
_exptl_absorpt_correction_T_max  0.454
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.55a (Rigaku Oxford Diffraction, 2022) Numerical 
absorption correction based on gaussian integration over a multifaceted 
crystal model Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 1 0 0.1196
1 -1 0 0.1257
1 1 0 0.1157
-1 -1 0 0.1248
-1 0 0 0.1393
0 -1 0 0.1299
1 0 0 0.1375
0 1 0 0.1535
0 0 -1 0.0408
0 0 1 0.0298

_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-R'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 
   # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
 --------------------------------------------------------------------------
   1  ω     41.00 110.00   0.50    0.05    --   58.61  18.00  96.00  138
   2  ω   -111.00 -43.00   0.50    0.05    --  -60.19 -18.00 -71.00  136
   3  ω   -121.00 -53.00   0.50    0.05    --  -69.72 -18.00 -71.00  136
   4  ω   -127.00 -59.00   0.50    0.05    --  -76.37 -18.00 -71.00  136
   5  ω     64.00 133.00   0.50    0.05    --   82.31  18.00  96.00  138
   6  ω     55.00  90.00   0.50    0.05    --   42.00  52.00 179.78   70
   7  ω     59.00  94.00   0.50    0.05    --   46.00  52.00 139.84   70
   8  ω     59.00  96.00   0.50    0.05    --   46.00  44.00-136.02   74
   9  ω     16.00  66.00   0.50    0.05    --   58.61 -95.00-120.00  100
  10  ω     53.00 122.00   0.50    0.05    --   71.30  18.00  96.00  138
  11  ω   -122.00 -87.00   0.50    0.05    --  -74.00 -54.00 -78.82   70
  12  ω    -97.00 -28.00   0.50    0.05    --  -76.37 112.00-150.00  138
  13  ω   -108.00 -38.00   0.50    0.05    --  -79.50 140.00 124.14  140
  14  ω   -131.00 -94.00   0.50    0.05    --  -79.50 -34.00 -74.94   74
  15  ω   -128.00-103.00   0.50    0.05    --  -79.50-116.00 -37.05   50
  16  ω   -118.00 -92.00   0.50    0.05    --  -79.50 -63.00  14.15   52
  17  ω   -124.00 -96.00   0.50    0.05    --  -79.50 -65.00-148.31   56
  18  ω   -120.00 -95.00   0.50    0.05    --  -79.50 -60.00-119.25   50
  19  ω   -127.00-102.00   0.50    0.05    --  -79.50 -50.00 -38.10   50
  20  ω   -114.00 -88.00   0.50    0.05    --  -79.50-135.00 -21.17   52
  21  ω   -121.00 -91.00   0.50    0.05    --  -79.50 -61.00  -7.71   60
  22  ω   -118.00 -92.00   0.50    0.05    --  -79.50 -53.00  89.10   52
  23  ω   -122.00 -97.00   0.50    0.05    --  -79.50 -63.00  58.52   50
  24  ω     44.00  94.00   0.50    0.05    --   82.31-112.00-180.00  100
  25  ω     54.00  88.00   0.50    0.05    --   82.31 -95.00-120.00   68
  26  ω     46.00  75.00   0.50    0.05    --   82.31 -95.00  60.00   58
  27  ω     47.00  73.00   0.50    0.05    --   82.31 -95.00 -90.00   52
  28  ω     34.00  95.00   0.50    0.05    --   82.31-112.00   0.00  122
  29  ω     44.00  97.00   0.50    0.05    --   82.31-112.00-120.00  106
  30  ω     40.00  66.00   0.50    0.05    --   82.31 -95.00 -60.00   52

;
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 HPA
_diffrn_detector_type            'HyPix Arc150'
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            13105
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.401
_diffrn_reflns_theta_max         73.603
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2596
_reflns_number_gt                2519
_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       'CrysAlisPro 1.171.42.55a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.55a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.55a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (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)+(0.1044P)²+1.4749P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2596
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1282
_refine_ls_wR_factor_gt          0.1275
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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
Br1 Br 0.10922(2) 0.46058(2) 0.37839(2) 0.02702(17) Uani 1 1 d . . . . .
O1 O 0.3945(2) 0.57935(16) 0.68826(19) 0.0375(5) Uani 1 1 d . . . . .
C1 C 0.3381(3) 0.55199(19) 0.6238(3) 0.0294(7) Uani 1 1 d . . . . .
Mn1 Mn 0.24576(4) 0.51377(3) 0.51967(4) 0.02474(18) Uani 1 1 d . . . . .
C3 C 0.1738(3) 0.6049(2) 0.5188(2) 0.0305(7) Uani 1 1 d . . . . .
O3 O 0.1308(2) 0.66446(14) 0.5174(2) 0.0381(6) Uani 1 1 d . . . . .
C2 C 0.3312(3) 0.55094(19) 0.4153(3) 0.0296(6) Uani 1 1 d . . . . .
O2 O 0.3861(2) 0.57520(16) 0.3513(2) 0.0378(5) Uani 1 1 d . . . . .
N1_1 N 0.1493(2) 0.46065(15) 0.6315(2) 0.0284(6) Uani 1 1 d . . . . .
H1A_1 H 0.146968 0.491042 0.691874 0.034 Uiso 1 1 calc R U . . .
H1B_1 H 0.080788 0.456001 0.602256 0.034 Uiso 1 1 calc R U . . .
C2_1 C 0.1901(2) 0.38429(19) 0.6621(2) 0.0280(6) Uani 1 1 d . . . . .
C3_1 C 0.1519(3) 0.34080(19) 0.7450(3) 0.0298(6) Uani 1 1 d . . . . .
H3_1 H 0.094370 0.359905 0.785732 0.036 Uiso 1 1 calc R U . . .
C4_1 C 0.1982(3) 0.2673(2) 0.7697(3) 0.0357(7) Uani 1 1 d . . . . .
H4_1 H 0.171445 0.237383 0.827424 0.043 Uiso 1 1 calc R U . . .
C5_1 C 0.2809(3) 0.2387(2) 0.7121(3) 0.0357(7) Uani 1 1 d . . . . .
H5_1 H 0.310660 0.189032 0.729224 0.043 Uiso 1 1 calc R U . . .
C6_1 C 0.3220(3) 0.28319(19) 0.6269(3) 0.0298(6) Uani 1 1 d . . . . .
C7_1 C 0.4077(3) 0.25769(19) 0.5624(3) 0.0325(7) Uani 1 1 d . . . . .
H7_1 H 0.440554 0.208349 0.575088 0.039 Uiso 1 1 calc R U . . .
C8_1 C 0.4418(3) 0.3051(2) 0.4823(3) 0.0332(7) Uani 1 1 d . . . . .
H8_1 H 0.497755 0.288333 0.437682 0.040 Uiso 1 1 calc R U . . .
C9_1 C 0.3945(3) 0.37864(19) 0.4657(2) 0.0297(6) Uani 1 1 d . . . . .
H9_1 H 0.420280 0.411043 0.410029 0.036 Uiso 1 1 calc R U . . .
N10_1 N 0.3151(2) 0.40476(15) 0.52462(19) 0.0260(5) Uani 1 1 d . . . . .
C11_1 C 0.2772(2) 0.35684(18) 0.6031(2) 0.0259(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Mn1 2.5392(5) . ?
O1 C1 1.135(4) . ?
C1 Mn1 1.802(3) . ?
Mn1 C3 1.801(3) . ?
Mn1 C2 1.820(4) . ?
Mn1 N10_1 2.060(3) . ?
Mn1 N1_1 2.079(3) . ?
C3 O3 1.154(4) . ?
C2 O2 1.145(4) . ?
N1_1 C2_1 1.449(4) . ?
C2_1 C3_1 1.369(4) . ?
C2_1 C11_1 1.411(4) . ?
C3_1 C4_1 1.414(5) . ?
C4_1 C5_1 1.366(5) . ?
C5_1 C6_1 1.412(5) . ?
C6_1 C11_1 1.407(4) . ?
C6_1 C7_1 1.426(4) . ?
C7_1 C8_1 1.362(5) . ?
C8_1 C9_1 1.404(5) . ?
C9_1 N10_1 1.330(4) . ?
N10_1 C11_1 1.370(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 Mn1 176.9(3) . . ?
C3 Mn1 C1 89.15(14) . . ?
C3 Mn1 C2 89.74(14) . . ?
C1 Mn1 C2 90.25(15) . . ?
C3 Mn1 N10_1 174.75(12) . . ?
C1 Mn1 N10_1 93.45(12) . . ?
C2 Mn1 N10_1 94.80(13) . . ?
C3 Mn1 N1_1 94.87(12) . . ?
C1 Mn1 N1_1 93.08(13) . . ?
C2 Mn1 N1_1 174.34(13) . . ?
N10_1 Mn1 N1_1 80.45(10) . . ?
C3 Mn1 Br1 89.70(10) . . ?
C1 Mn1 Br1 177.56(10) . . ?
C2 Mn1 Br1 91.89(10) . . ?
N10_1 Mn1 Br1 87.52(7) . . ?
N1_1 Mn1 Br1 84.87(8) . . ?
O3 C3 Mn1 177.8(3) . . ?
O2 C2 Mn1 178.5(3) . . ?
C2_1 N1_1 Mn1 111.4(2) . . ?
C3_1 C2_1 C11_1 120.2(3) . . ?
C3_1 C2_1 N1_1 123.9(3) . . ?
C11_1 C2_1 N1_1 115.8(3) . . ?
C2_1 C3_1 C4_1 119.8(3) . . ?
C5_1 C4_1 C3_1 121.1(3) . . ?
C4_1 C5_1 C6_1 119.9(3) . . ?
C11_1 C6_1 C5_1 119.2(3) . . ?
C11_1 C6_1 C7_1 117.2(3) . . ?
C5_1 C6_1 C7_1 123.6(3) . . ?
C8_1 C7_1 C6_1 119.1(3) . . ?
C7_1 C8_1 C9_1 120.1(3) . . ?
N10_1 C9_1 C8_1 122.6(3) . . ?
C9_1 N10_1 C11_1 118.1(3) . . ?
C9_1 N10_1 Mn1 127.6(2) . . ?
C11_1 N10_1 Mn1 114.23(19) . . ?
N10_1 C11_1 C6_1 122.8(3) . . ?
N10_1 C11_1 C2_1 117.3(3) . . ?
C6_1 C11_1 C2_1 119.8(3) . . ?

_refine_diff_density_max         1.503
_refine_diff_density_min         -1.268
_refine_diff_density_rms         0.157


_chemical_properties_physical    Light-sensitive
