# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_cmpd_6
_database_code_depnum_ccdc_archive 'CCDC 1999560'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich '
;Institute of Inorganic Chemistry, Wuerzburg University, Am Hubland, Wuerzburg, Germany
Germany
;
_audit_update_record             
;
2020-04-27 deposited with the CCDC.	2020-06-09 downloaded from the CCDC.
;

_audit_creation_date             2020-04-20
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.03.02 svn.r3394 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2018/3

_chemical_formula_moiety         'C19 H11 Br Mn N3 O5'
_chemical_formula_sum            'C19 H11 Br Mn N3 O5'
_chemical_formula_weight         496.16

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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8628(2)
_cell_length_b                   16.1907(4)
_cell_length_c                   34.5806(7)
_cell_angle_alpha                90.292(2)
_cell_angle_beta                 92.660(2)
_cell_angle_gamma                92.168(2)
_cell_volume                     3835.38(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    23184
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.0720
_cell_measurement_theta_min      2.7140
_shelx_estimated_absorpt_T_max   0.488
_shelx_estimated_absorpt_T_min   0.238
_exptl_absorpt_coefficient_mu    8.376
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.227
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.43a (Rigaku Oxford Diffraction, 2019) 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   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1968
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0595
2 1 2 0.1175
-2 2 -1 0.0947
1 -10 8 0.0948
3 6 7 0.1219
0 10 -6 0.0977
-4 4 -8 0.0965
4 -4 8 0.1012
0 -10 4 0.0990
0 7 -16 0.0697
0 0 -22 0.0729
-4 -3 8 0.0918
4 -4 -8 0.1029
-1 -4 21 0.0456
1 4 -20 0.0516
-3 -6 7 0.0822
0 -7 -16 0.0931
0 7 16 0.1029

_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.102
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0005 -0.0047 1.0008 -0.0433 -0.0066 0.0087
1.9970 0.6355 2.0171 0.0048 -0.3136 0.3478
-1.9982 2.3596 -1.0326 -0.0286 0.4841 -0.1159
0.9066 -9.6333 8.0513 -0.3682 -0.7731 -0.5164
3.2376 5.9586 6.8507 -0.1160 -0.2408 0.9636
-0.0029 10.1941 -5.5410 0.3031 0.6371 0.7087
-3.6864 4.3849 -8.3335 0.2251 0.9362 -0.2699
3.6797 -4.4225 8.3268 -0.2254 -0.9372 0.2661
0.1720 -10.3410 4.1112 -0.2348 -0.6652 -0.7088
0.1756 7.4347 -15.9283 0.7423 0.5106 0.4339
-0.0997 0.3088 -22.3883 0.9645 0.1785 -0.1947
-3.9266 -3.2664 8.2177 -0.5483 0.4197 -0.7233
3.8680 -4.4689 -7.6408 0.4723 -0.8696 0.1440
-0.9746 -3.5614 20.7267 -0.9604 -0.1777 -0.2145
1.1820 4.1749 -19.9309 0.9390 0.1736 0.2968
-3.3567 -6.0448 6.6932 -0.4748 0.1692 -0.8637
-0.1189 -7.2605 -16.0334 0.6417 -0.3053 -0.7036
0.1009 7.2403 16.0858 -0.6449 0.3068 0.7000

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1281
_diffrn_reflns_av_unetI/netI     0.0946
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            55706
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.066
_diffrn_reflns_theta_max         67.066
_diffrn_reflns_theta_min         2.558
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -83.00  -2.00   0.50    0.31    --  -47.45 111.00  55.00  162
  2  ω    -51.00 -14.00   0.50    2.00    --  -86.25  45.00   0.00   74
  3  ω    -26.00  28.00   0.50    0.31    --  -47.45  19.00 -30.00  108
  4  ω    -42.00  26.00   0.50    0.31    --  -47.45  37.00 -90.00  136
  5  ω    -27.00  26.00   0.50    0.31    --   47.45 -19.00 -60.00  106
  6  ω     24.00  88.00   0.50    0.31    --   47.45-111.00 -38.00  128
  7  ω     34.00  95.00   0.50    0.31    --   47.45-125.00 -90.00  122
  8  ω     35.00 108.00   0.50    2.00    --  107.75-111.00 -38.00  146
  9  ω     97.00 128.00   0.50    2.00    --  107.75-147.00  -3.64   62
 10  ω     80.00 106.00   0.50    2.00    --  107.75-108.00-112.79   52
 11  ω     87.00 124.00   0.50    2.00    --  107.75-141.00-153.12   74
 12  ω     68.00 110.00   0.50    2.00    --  107.75-125.00-120.00   84
 13  ω     56.00 132.00   0.50    2.00    --  107.75-154.00 -24.74  152
 14  ω     76.00 107.00   0.50    2.00    --  107.75-108.00  72.79   62
 15  ω     86.00 119.00   0.50    2.00    --  107.75-143.00 114.18   66
 16  ω     70.00 108.00   0.50    2.00    --  107.75-111.00 132.13   76
 17  ω     60.00 112.00   0.50    2.00    --  107.75-125.00  30.00  104
 18  ω     68.00  96.00   0.50    2.00    --  107.75 -94.00  30.00   56
 19  ω     71.00  96.00   0.50    2.00    --  107.75 -94.00   0.00   50
 20  ω     63.00  90.00   0.50    2.00    --  107.75-147.00  -3.64   54
 21  ω     35.00 106.00   0.50    2.00    --  107.75 -77.00  60.00  142
 22  ω     56.00  82.00   0.50    2.00    --  107.75-143.00 114.18   52
 23  ω     42.00  71.00   0.50    2.00    --  107.75-108.00  72.79   58
 24  ω     42.00  67.00   0.50    2.00    --  107.75 -77.00   0.00   50
 25  ω     37.00 107.00   0.50    2.00    --  107.75-107.00 -11.62  140
 26  ω     53.00  89.00   0.50    2.00    --  107.75 -77.00-120.00   72
 27  ω     55.00 107.00   0.50    2.00    --  107.75-125.00-180.00  104
 28  ω     48.00  79.00   0.50    2.00    --  107.75-141.00-153.12   62
 29  ω     36.00 108.00   0.50    2.00    --  107.75-125.00 -90.00  144
 30  ω     38.00  67.00   0.50    2.00    --  107.75 -61.00-120.00   58
 31  ω     35.00  71.00   0.50    2.00    --  107.75 -61.00-180.00   72
 32  ω     36.00 111.00   0.50    2.00    --  107.75-125.00-150.00  150
 33  ω     37.00  65.00   0.50    2.00    --  107.75-125.00-120.00   56
 34  ω     36.00  70.00   0.50    2.00    --  107.75 -61.00 -30.00   68
 35  ω     39.00  69.00   0.50    2.00    --  107.75 -61.00   0.00   60
 36  ω     37.00  63.00   0.50    2.00    --  107.75 -94.00  30.00   52
 37  ω     38.00  71.00   0.50    2.00    --  107.75 -61.00  90.00   66
 38  ω     35.00  64.00   0.50    2.00    --  107.75-111.00 132.13   58
 39  ω     35.00 104.00   0.50    2.00    --  107.75-125.00 120.00  138
 40  ω     94.00 178.00   0.50    2.00    --  107.75  15.00  30.00  168
 41  ω    114.00 168.00   0.50    2.00    --  107.75  61.00  60.00  108
 42  ω    119.00 158.00   0.50    2.00    --  107.75 125.00   0.00   78
 43  ω    114.00 178.00   0.50    2.00    --  107.75 125.00 -60.00  128
 44  ω    142.00 169.00   0.50    2.00    --  107.75 125.00 -90.00   54
 45  ω    107.00 175.00   0.50    2.00    --  107.75  61.00  30.00  136
 46  ω    103.00 178.00   0.50    2.00    --  107.75 111.00  55.00  150
 47  ω     95.00 178.00   0.50    2.00    --  107.75  30.00 120.00  166
 48  ω     96.00 149.00   0.50    2.00    --  107.75  45.00 -30.00  106
 49  ω     94.00 178.00   0.50    2.00    --  107.75  15.00  60.00  168
 50  ω    102.00 128.00   0.50    2.00    --  107.75  30.00 150.00   52
 51  ω     92.00 175.00   0.50    2.00    --  107.75  61.00  90.00  166
 52  ω     95.00 142.00   0.50    2.00    --  107.75 125.00 -30.00   94
 53  ω     91.00 162.00   0.50    2.00    --  107.75  61.00 -30.00  142
 54  ω     96.00 134.00   0.50    2.00    --  107.75 125.00 -90.00   76
 55  ω    -24.00  62.00   0.50    0.31    --   47.45 -57.00  90.00  172
 56  ω    -82.00 -13.00   0.50    2.00    --  -86.25 111.00  55.00  138
 57  ω   -159.00 -65.00   0.50    2.00    --  -86.25 -72.00  39.85  188
 58  ω   -120.00 -73.00   0.50    0.31    --  -47.45-125.00   0.00   94
 59  ω   -120.00 -73.00   0.50    0.31    --  -47.45-125.00 -90.00   94
 60  ω   -120.00 -73.00   0.50    0.31    --  -47.45-125.00-120.00   94
 61  ω   -159.00 -81.00   0.50    2.00    --  -86.25-111.00 -38.00  156
 62  ω   -120.00 -73.00   0.50    0.31    --  -47.45-125.00 150.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0440237000
_diffrn_orient_matrix_UB_12      0.0062717000
_diffrn_orient_matrix_UB_13      -0.0431898000
_diffrn_orient_matrix_UB_21      -0.1693461000
_diffrn_orient_matrix_UB_22      0.0589647000
_diffrn_orient_matrix_UB_23      -0.0064034000
_diffrn_orient_matrix_UB_31      0.1412718000
_diffrn_orient_matrix_UB_32      0.0745048000
_diffrn_orient_matrix_UB_33      0.0090946000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                10089
_reflns_number_total             13158
_reflns_odcompleteness_completeness 92.07
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.962
_refine_diff_density_min         -1.293
_refine_diff_density_rms         0.210
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1046
_refine_ls_number_reflns         13158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1198
_refine_ls_R_factor_gt           0.0981
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1560P)²+28.5257P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2706
_refine_ls_wR_factor_ref         0.2852
_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and 
goodness of fit S are based on F², conventional R-factors R are based on F, 
with F set to zero for negative F². The threshold expression of F² > 
2sigma(F²) is used only for calculating R-factors(gt) etc. and is not 
relevant to the choice of reflections for refinement. R-factors based on F² 
are statistically about twice as large as those based on F, and R-factors 
based on ALL data will be even larger.
The single crystal showed a high mosaicity with the reflections spanning 
several frames. This led in combination with a long c lattice parameter to 
partly too high reflection intensities from data reduction, which is a result
of overlap with other reflections? tails. Further, the crystal was a 
non-merohedral twin with a small twin fraction of ca. 8%. Only the strong 
domain was considered during data reduction, while a minor twin fraction of
0.5% with a 180° twin rotation around reciprocal axis (0 1 0) was refined 
in the least-squares procedure. In summary, weak reflection intensities at 
high resolution, high crystal mosaicity, twinning, and a crystal jump during
data collection had a restricting effect on the data quality and, hence, 
tructure refinement results.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.9946(5)
 0.0054(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C15(H15),
 C16(H16), C18(H18), C19(H19), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10),
 C11(H11), C13(H13), C15(H15), C16(H16), C18(H18), C19(H19), C5(H5), C6(H6),
 C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C15(H15), C16(H16), C18(H18),
 C19(H19), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C15(H15), C16(H16), C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.28396(14) 0.27601(6) 0.45405(3) 0.0401(3) Uani 1 1 d . . . . .
Mn1 Mn 0.4955(2) 0.20559(8) 0.50487(5) 0.0327(4) Uani 1 1 d . . . . .
O1 O 0.7248(11) 0.1263(4) 0.5673(2) 0.0471(18) Uani 1 1 d . . . . .
O2 O 0.3490(11) 0.0443(4) 0.4720(2) 0.0442(17) Uani 1 1 d . . . . .
O4 O 0.9506(13) -0.0751(5) 0.3680(3) 0.063(2) Uani 1 1 d . . . . .
O5 O 0.9600(12) 0.0199(6) 0.3240(3) 0.063(2) Uani 1 1 d . . . . .
O3 O 0.1285(12) 0.1937(5) 0.5469(3) 0.058(2) Uani 1 1 d . . . . .
N1 N 0.5985(11) 0.3224(4) 0.5236(2) 0.0336(17) Uani 1 1 d . . . . .
N2 N 0.7161(11) 0.2285(5) 0.4676(3) 0.0362(18) Uani 1 1 d . . . . .
N3 N 0.9376(12) -0.0036(7) 0.3577(3) 0.053(3) Uani 1 1 d . . . . .
C1 C 0.6388(15) 0.1563(6) 0.5421(3) 0.039(2) Uani 1 1 d . . . . .
C2 C 0.4122(14) 0.1073(6) 0.4843(3) 0.037(2) Uani 1 1 d . . . . .
C3 C 0.2731(16) 0.2000(5) 0.5322(3) 0.044(3) Uani 1 1 d . . . . .
C4 C 0.5631(13) 0.3665(5) 0.5564(3) 0.033(2) Uani 1 1 d . . . . .
C5 C 0.4872(13) 0.3262(6) 0.5888(3) 0.035(2) Uani 1 1 d . . . . .
H5 H 0.450745 0.269022 0.587154 0.042 Uiso 1 1 calc R . . . .
C6 C 0.4656(15) 0.3687(6) 0.6226(3) 0.042(2) Uani 1 1 d . . . . .
H6 H 0.422459 0.340169 0.644757 0.051 Uiso 1 1 calc R . . . .
C7 C 0.5075(15) 0.4549(6) 0.6246(3) 0.041(2) Uani 1 1 d . . . . .
H7 H 0.488060 0.484764 0.647702 0.049 Uiso 1 1 calc R . . . .
C8 C 0.5761(15) 0.4948(6) 0.5930(3) 0.042(2) Uani 1 1 d . . . . .
H8 H 0.598987 0.553049 0.594038 0.051 Uiso 1 1 calc R . . . .
C9 C 0.6128(13) 0.4522(6) 0.5595(3) 0.037(2) Uani 1 1 d . . . . .
C10 C 0.7061(14) 0.4912(6) 0.5275(3) 0.040(2) Uani 1 1 d . . . . .
H10 H 0.730316 0.549318 0.527496 0.048 Uiso 1 1 calc R . . . .
C11 C 0.7589(15) 0.4443(6) 0.4975(3) 0.038(2) Uani 1 1 d . . . . .
H11 H 0.831734 0.468593 0.477545 0.046 Uiso 1 1 calc R . . . .
C12 C 0.7065(12) 0.3603(5) 0.4960(3) 0.033(2) Uani 1 1 d . . . . .
C13 C 0.7721(13) 0.3050(6) 0.4666(3) 0.036(2) Uani 1 1 d . . . . .
H13 H 0.854451 0.324831 0.447030 0.043 Uiso 1 1 calc R . . . .
C14 C 0.7807(13) 0.1718(6) 0.4403(3) 0.034(2) Uani 1 1 d . . . . .
C15 C 0.7957(14) 0.1950(6) 0.4013(3) 0.041(2) Uani 1 1 d . . . . .
H15 H 0.767344 0.249490 0.393423 0.050 Uiso 1 1 calc R . . . .
C16 C 0.8524(16) 0.1376(7) 0.3747(3) 0.047(3) Uani 1 1 d . . . . .
H16 H 0.865515 0.152631 0.348387 0.056 Uiso 1 1 calc R . . . .
C17 C 0.8890(14) 0.0593(7) 0.3865(3) 0.046(3) Uani 1 1 d . . . . .
C18 C 0.8805(14) 0.0351(6) 0.4249(3) 0.042(2) Uani 1 1 d . . . . .
H18 H 0.912846 -0.019053 0.432700 0.050 Uiso 1 1 calc R . . . .
C19 C 0.8235(14) 0.0926(6) 0.4512(3) 0.039(2) Uani 1 1 d . . . . .
H19 H 0.813464 0.077252 0.477555 0.047 Uiso 1 1 calc R . . . .
Br1_1 Br 0.39833(15) 0.20281(6) 0.71083(3) 0.0417(3) Uani 1 1 d . . . . .
Mn1_1 Mn 0.6350(2) 0.27903(9) 0.75800(5) 0.0345(4) Uani 1 1 d . . . . .
O1_1 O 0.8872(13) 0.3741(5) 0.8146(3) 0.059(2) Uani 1 1 d . . . . .
O2_1 O 0.4971(11) 0.4323(4) 0.7217(2) 0.0467(18) Uani 1 1 d . . . . .
O3_1 O 0.2795(12) 0.2881(6) 0.8032(3) 0.059(2) Uani 1 1 d . . . . .
O4_1 O 1.0695(11) 0.5265(5) 0.5992(3) 0.058(2) Uani 1 1 d . . . . .
O5_1 O 1.0863(11) 0.4153(5) 0.5633(2) 0.0518(19) Uani 1 1 d . . . . .
N1_1 N 0.7334(11) 0.1680(5) 0.7795(2) 0.0353(18) Uani 1 1 d . . . . .
N2_1 N 0.8378(11) 0.2510(5) 0.7194(2) 0.0341(17) Uani 1 1 d . . . . .
N3_1 N 1.0584(12) 0.4515(6) 0.5941(3) 0.048(2) Uani 1 1 d . . . . .
C1_1 C 0.7924(16) 0.3374(6) 0.7921(4) 0.045(3) Uani 1 1 d . . . . .
C2_1 C 0.5548(15) 0.3726(6) 0.7349(3) 0.042(2) Uani 1 1 d . . . . .
C3_1 C 0.4202(19) 0.2849(7) 0.7870(4) 0.052(3) Uani 1 1 d . . . . .
C4_1 C 0.7088(13) 0.1305(6) 0.8146(3) 0.035(2) Uani 1 1 d . . . . .
C5_1 C 0.6414(14) 0.1769(6) 0.8469(3) 0.037(2) Uani 1 1 d . . . . .
H5_1 H 0.605357 0.232565 0.843482 0.045 Uiso 1 1 calc R . . . .
C6_1 C 0.6295(14) 0.1414(6) 0.8819(3) 0.042(2) Uani 1 1 d . . . . .
H6_1 H 0.593652 0.173535 0.903311 0.050 Uiso 1 1 calc R . . . .
C7_1 C 0.6691(15) 0.0582(7) 0.8872(3) 0.047(3) Uani 1 1 d . . . . .
H7_1 H 0.653482 0.033990 0.911851 0.056 Uiso 1 1 calc R . . . .
C8_1 C 0.7300(14) 0.0109(6) 0.8575(3) 0.041(2) Uani 1 1 d . . . . .
H8_1 H 0.755468 -0.045753 0.861665 0.049 Uiso 1 1 calc R . . . .
C9_1 C 0.7554(13) 0.0465(6) 0.8201(3) 0.035(2) Uani 1 1 d . . . . .
C10_1 C 0.8394(14) 0.0033(6) 0.7908(3) 0.040(2) Uani 1 1 d . . . . .
H10_1 H 0.865477 -0.053640 0.793694 0.048 Uiso 1 1 calc R . . . .
C11_1 C 0.8838(14) 0.0444(6) 0.7576(3) 0.038(2) Uani 1 1 d . . . . .
H11_1 H 0.949919 0.017705 0.737829 0.045 Uiso 1 1 calc R . . . .
C12_1 C 0.8302(14) 0.1260(6) 0.7535(3) 0.038(2) Uani 1 1 d . . . . .
C13_1 C 0.8899(14) 0.1757(6) 0.7197(3) 0.037(2) Uani 1 1 d . . . . .
H13_1 H 0.962025 0.153164 0.699630 0.044 Uiso 1 1 calc R . . . .
C14_1 C 0.8966(13) 0.2999(6) 0.6874(3) 0.034(2) Uani 1 1 d . . . . .
C15_1 C 0.8980(14) 0.2669(6) 0.6500(3) 0.042(2) Uani 1 1 d . . . . .
H15_1 H 0.860040 0.210542 0.645407 0.050 Uiso 1 1 calc R . . . .
C16_1 C 0.9543(14) 0.3159(7) 0.6200(3) 0.047(3) Uani 1 1 d . . . . .
H16_1 H 0.959290 0.293426 0.594611 0.056 Uiso 1 1 calc R . . . .
C17_1 C 1.0036(14) 0.3979(7) 0.6269(4) 0.045(2) Uani 1 1 d . . . . .
C18_1 C 1.0035(14) 0.4328(6) 0.6635(3) 0.042(2) Uani 1 1 d . . . . .
H18_1 H 1.039092 0.489591 0.667628 0.051 Uiso 1 1 calc R . . . .
C19_1 C 0.9506(14) 0.3833(6) 0.6939(3) 0.041(2) Uani 1 1 d . . . . .
H19_1 H 0.950754 0.405788 0.719283 0.049 Uiso 1 1 calc R . . . .
Br1_2 Br 0.66616(16) 0.29348(7) 0.98382(4) 0.0527(3) Uani 1 1 d . . . . .
Mn1_2 Mn 0.9153(2) 0.21149(9) 1.02146(5) 0.0368(4) Uani 1 1 d . . . . .
O1_2 O 1.1866(12) 0.1113(5) 1.0675(3) 0.054(2) Uani 1 1 d . . . . .
O2_2 O 0.7193(12) 0.0602(4) 0.9881(2) 0.052(2) Uani 1 1 d . . . . .
O3_2 O 0.6111(12) 0.1969(6) 1.0798(3) 0.063(2) Uani 1 1 d . . . . .
O4_2 O 1.2230(14) -0.0515(6) 0.8577(3) 0.071(3) Uani 1 1 d . . . . .
O5_2 O 1.2551(12) 0.0556(6) 0.8200(3) 0.063(2) Uani 1 1 d . . . . .
N1_2 N 1.0553(12) 0.3228(5) 1.0394(3) 0.0382(18) Uani 1 1 d . . . . .
N2_2 N 1.0934(11) 0.2356(5) 0.9769(2) 0.0360(18) Uani 1 1 d . . . . .
N3_2 N 1.2232(13) 0.0231(7) 0.8517(3) 0.057(3) Uani 1 1 d . . . . .
C1_2 C 1.0828(16) 0.1504(6) 1.0496(3) 0.038(2) Uani 1 1 d . . . . .
C2_2 C 0.7949(17) 0.1189(6) 1.0001(3) 0.046(3) Uani 1 1 d . . . . .
C3_2 C 0.7350(17) 0.2036(7) 1.0582(4) 0.052(3) Uani 1 1 d . . . . .
C4_2 C 1.0511(14) 0.3655(6) 1.0738(3) 0.040(2) Uani 1 1 d . . . . .
C5_2 C 0.9982(14) 0.3233(6) 1.1077(3) 0.041(2) Uani 1 1 d . . . . .
H5_2 H 0.959962 0.266283 1.106175 0.049 Uiso 1 1 calc R . . . .
C6_2 C 1.0012(15) 0.3633(7) 1.1427(3) 0.046(3) Uani 1 1 d . . . . .
H6_2 H 0.969964 0.333673 1.165385 0.055 Uiso 1 1 calc R . . . .
C7_2 C 1.0513(15) 0.4491(7) 1.1450(4) 0.051(3) Uani 1 1 d . . . . .
H7_2 H 1.048174 0.477341 1.169104 0.061 Uiso 1 1 calc R . . . .
C8_2 C 1.1040(16) 0.4914(7) 1.1126(4) 0.051(3) Uani 1 1 d . . . . .
H8_2 H 1.136278 0.548902 1.114546 0.061 Uiso 1 1 calc R . . . .
C9_2 C 1.1110(14) 0.4512(6) 1.0769(3) 0.043(2) Uani 1 1 d . . . . .
C10_2 C 1.1872(15) 0.4901(6) 1.0448(4) 0.046(3) Uani 1 1 d . . . . .
H10_2 H 1.221491 0.547534 1.045731 0.055 Uiso 1 1 calc R . . . .
C11_2 C 1.2127(15) 0.4444(6) 1.0116(3) 0.044(2) Uani 1 1 d . . . . .
H11_2 H 1.276080 0.468468 0.990308 0.052 Uiso 1 1 calc R . . . .
C12_2 C 1.1428(13) 0.3614(6) 1.0100(3) 0.037(2) Uani 1 1 d . . . . .
C13_2 C 1.1671(14) 0.3097(6) 0.9771(3) 0.037(2) Uani 1 1 d . . . . .
H13_2 H 1.236488 0.329826 0.955701 0.045 Uiso 1 1 calc R . . . .
C14_2 C 1.1238(14) 0.1824(6) 0.9446(3) 0.041(2) Uani 1 1 d . . . . .
C15_2 C 1.1066(14) 0.2110(7) 0.9068(3) 0.045(3) Uani 1 1 d . . . . .
H15_2 H 1.072555 0.266453 0.901978 0.054 Uiso 1 1 calc R . . . .
C16_2 C 1.1389(14) 0.1590(7) 0.8764(3) 0.046(3) Uani 1 1 d . . . . .
H16_2 H 1.130602 0.178613 0.850540 0.055 Uiso 1 1 calc R . . . .
C17_2 C 1.1832(15) 0.0784(7) 0.8837(3) 0.044(3) Uani 1 1 d . . . . .
C18_2 C 1.1989(16) 0.0485(7) 0.9218(4) 0.053(3) Uani 1 1 d . . . . .
H18_2 H 1.229034 -0.007365 0.926703 0.064 Uiso 1 1 calc R . . . .
C19_2 C 1.1697(16) 0.1021(6) 0.9517(4) 0.047(3) Uani 1 1 d . . . . .
H19_2 H 1.181440 0.083296 0.977599 0.057 Uiso 1 1 calc R . . . .
Br1_3 Br 0.05091(16) 0.22143(7) 0.22835(4) 0.0544(4) Uani 1 1 d . . . . .
Mn1_3 Mn 0.3136(2) 0.30175(9) 0.26740(5) 0.0402(4) Uani 1 1 d . . . . .
O1_3 O 0.6162(14) 0.3898(5) 0.3168(3) 0.067(3) Uani 1 1 d . . . . .
O2_3 O 0.1283(12) 0.4564(5) 0.2438(3) 0.054(2) Uani 1 1 d . . . . .
O3_3 O 0.0220(16) 0.3090(7) 0.3277(4) 0.084(3) Uani 1 1 d . . . . .
O4_3 O 0.6433(17) 0.6064(6) 0.1184(3) 0.082(3) Uani 1 1 d . . . . .
O5_3 O 0.6296(14) 0.5092(7) 0.0739(3) 0.071(3) Uani 1 1 d . . . . .
N1_3 N 0.4395(12) 0.1875(5) 0.2774(3) 0.041(2) Uani 1 1 d . . . . .
N2_3 N 0.4845(11) 0.2921(5) 0.2206(2) 0.0358(18) Uani 1 1 d . . . . .
N3_3 N 0.6218(14) 0.5339(7) 0.1074(4) 0.060(3) Uani 1 1 d . . . . .
C1_3 C 0.4998(18) 0.3551(6) 0.2977(4) 0.050(3) Uani 1 1 d . . . . .
C2_3 C 0.2045(17) 0.3961(6) 0.2519(3) 0.046(3) Uani 1 1 d . . . . .
C3_3 C 0.1391(19) 0.3038(8) 0.3062(4) 0.058(3) Uani 1 1 d . . . . .
C4_3 C 0.4278(13) 0.1362(5) 0.3089(3) 0.035(2) Uani 1 1 d . . . . .
C5_3 C 0.3637(15) 0.1644(6) 0.3443(3) 0.042(2) Uani 1 1 d . . . . .
H5_3 H 0.329910 0.220490 0.346825 0.051 Uiso 1 1 calc R . . . .
C6_3 C 0.3486(15) 0.1133(7) 0.3752(3) 0.044(2) Uani 1 1 d . . . . .
H6_3 H 0.304100 0.133776 0.398871 0.053 Uiso 1 1 calc R . . . .
C7_3 C 0.3997(17) 0.0287(7) 0.3722(4) 0.050(3) Uani 1 1 d . . . . .
H7_3 H 0.388318 -0.006905 0.393781 0.060 Uiso 1 1 calc R . . . .
C8_3 C 0.4639(15) -0.0007(6) 0.3386(4) 0.044(3) Uani 1 1 d . . . . .
H8_3 H 0.494633 -0.057221 0.336597 0.053 Uiso 1 1 calc R . . . .
C9_3 C 0.4861(14) 0.0520(5) 0.3062(3) 0.037(2) Uani 1 1 d . . . . .
C10_3 C 0.5721(14) 0.0252(6) 0.2730(3) 0.040(2) Uani 1 1 d . . . . .
H10_3 H 0.612143 -0.030117 0.270870 0.048 Uiso 1 1 calc R . . . .
C11_3 C 0.5985(14) 0.0806(6) 0.2430(3) 0.040(2) Uani 1 1 d . . . . .
H11_3 H 0.661722 0.065096 0.220352 0.048 Uiso 1 1 calc R . . . .
C12_3 C 0.5295(14) 0.1594(6) 0.2473(3) 0.038(2) Uani 1 1 d . . . . .
C13_3 C 0.5536(14) 0.2196(6) 0.2166(3) 0.039(2) Uani 1 1 d . . . . .
H13_3 H 0.619152 0.205768 0.194001 0.047 Uiso 1 1 calc R . . . .
C14_3 C 0.5136(14) 0.3515(6) 0.1909(3) 0.040(2) Uani 1 1 d . . . . .
C15_3 C 0.4922(14) 0.3316(6) 0.1523(3) 0.042(2) Uani 1 1 d . . . . .
H15_3 H 0.454577 0.276654 0.144613 0.050 Uiso 1 1 calc R . . . .
C16_3 C 0.5252(14) 0.3913(8) 0.1243(4) 0.048(3) Uani 1 1 d . . . . .
H16_3 H 0.509138 0.378047 0.097498 0.057 Uiso 1 1 calc R . . . .
C17_3 C 0.5813(15) 0.4694(7) 0.1363(4) 0.050(3) Uani 1 1 d . . . . .
C18_3 C 0.6047(15) 0.4925(6) 0.1757(4) 0.047(3) Uani 1 1 d . . . . .
H18_3 H 0.644502 0.547325 0.183217 0.057 Uiso 1 1 calc R . . . .
C19_3 C 0.5675(15) 0.4325(6) 0.2028(4) 0.044(3) Uani 1 1 d . . . . .
H19_3 H 0.578388 0.446010 0.229562 0.053 Uiso 1 1 calc R . . . .


_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 2.531(2) . ?
Mn1 N1 2.082(7) . ?
Mn1 N2 2.057(9) . ?
Mn1 C1 1.792(12) . ?
Mn1 C2 1.801(9) . ?
Mn1 C3 1.831(11) . ?
O1 C1 1.150(13) . ?
O2 C2 1.165(11) . ?
O4 N3 1.219(15) . ?
O5 N3 1.240(14) . ?
O3 C3 1.139(13) . ?
N1 C4 1.375(12) . ?
N1 C12 1.370(12) . ?
N2 C13 1.285(12) . ?
N2 C14 1.412(13) . ?
N3 C17 1.477(14) . ?
C4 C5 1.410(14) . ?
C4 C9 1.418(13) . ?
C5 H5 0.9500 . ?
C5 C6 1.370(15) . ?
C6 H6 0.9500 . ?
C6 C7 1.415(14) . ?
C7 H7 0.9500 . ?
C7 C8 1.365(16) . ?
C8 H8 0.9500 . ?
C8 C9 1.384(15) . ?
C9 C10 1.439(15) . ?
C10 H10 0.9500 . ?
C10 C11 1.354(15) . ?
C11 H11 0.9500 . ?
C11 C12 1.392(13) . ?
C12 C13 1.450(14) . ?
C13 H13 0.9500 . ?
C14 C15 1.407(15) . ?
C14 C19 1.377(14) . ?
C15 H15 0.9500 . ?
C15 C16 1.385(15) . ?
C16 H16 0.9500 . ?
C16 C17 1.362(17) . ?
C17 C18 1.390(17) . ?
C18 H18 0.9500 . ?
C18 C19 1.379(15) . ?
C19 H19 0.9500 . ?
Br1_1 Mn1_1 2.5305(18) . ?
Mn1_1 N1_1 2.073(8) . ?
Mn1_1 N2_1 2.035(8) . ?
Mn1_1 C1_1 1.801(11) . ?
Mn1_1 C2_1 1.808(12) . ?
Mn1_1 C3_1 1.825(14) . ?
O1_1 C1_1 1.140(14) . ?
O2_1 C2_1 1.148(14) . ?
O3_1 C3_1 1.143(15) . ?
O4_1 N3_1 1.225(13) . ?
O5_1 N3_1 1.239(13) . ?
N1_1 C4_1 1.373(13) . ?
N1_1 C12_1 1.340(13) . ?
N2_1 C13_1 1.283(13) . ?
N2_1 C14_1 1.428(12) . ?
N3_1 C17_1 1.485(14) . ?
C4_1 C5_1 1.448(14) . ?
C4_1 C9_1 1.421(13) . ?
C5_1 H5_1 0.9500 . ?
C5_1 C6_1 1.345(15) . ?
C6_1 H6_1 0.9500 . ?
C6_1 C7_1 1.396(16) . ?
C7_1 H7_1 0.9500 . ?
C7_1 C8_1 1.368(16) . ?
C8_1 H8_1 0.9500 . ?
C8_1 C9_1 1.434(15) . ?
C9_1 C10_1 1.388(15) . ?
C10_1 H10_1 0.9500 . ?
C10_1 C11_1 1.370(15) . ?
C11_1 H11_1 0.9500 . ?
C11_1 C12_1 1.391(14) . ?
C12_1 C13_1 1.489(15) . ?
C13_1 H13_1 0.9500 . ?
C14_1 C15_1 1.397(15) . ?
C14_1 C19_1 1.401(14) . ?
C15_1 H15_1 0.9500 . ?
C15_1 C16_1 1.372(16) . ?
C16_1 H16_1 0.9500 . ?
C16_1 C17_1 1.375(16) . ?
C17_1 C18_1 1.383(17) . ?
C18_1 H18_1 0.9500 . ?
C18_1 C19_1 1.378(15) . ?
C19_1 H19_1 0.9500 . ?
Br1_2 Mn1_2 2.522(2) . ?
Mn1_2 N1_2 2.088(8) . ?
Mn1_2 N2_2 2.041(9) . ?
Mn1_2 C1_2 1.801(12) . ?
Mn1_2 C2_2 1.820(11) . ?
Mn1_2 C3_2 1.817(12) . ?
O1_2 C1_2 1.134(13) . ?
O2_2 C2_2 1.133(13) . ?
O3_2 C3_2 1.158(14) . ?
O4_2 N3_2 1.227(15) . ?
O5_2 N3_2 1.244(15) . ?
N1_2 C4_2 1.373(14) . ?
N1_2 C12_2 1.349(13) . ?
N2_2 C13_2 1.285(12) . ?
N2_2 C14_2 1.436(13) . ?
N3_2 C17_2 1.461(15) . ?
C4_2 C5_2 1.417(15) . ?
C4_2 C9_2 1.434(13) . ?
C5_2 H5_2 0.9500 . ?
C5_2 C6_2 1.368(15) . ?
C6_2 H6_2 0.9500 . ?
C6_2 C7_2 1.420(15) . ?
C7_2 H7_2 0.9500 . ?
C7_2 C8_2 1.371(19) . ?
C8_2 H8_2 0.9500 . ?
C8_2 C9_2 1.397(17) . ?
C9_2 C10_2 1.392(16) . ?
C10_2 H10_2 0.9500 . ?
C10_2 C11_2 1.386(17) . ?
C11_2 H11_2 0.9500 . ?
C11_2 C12_2 1.410(13) . ?
C12_2 C13_2 1.429(15) . ?
C13_2 H13_2 0.9500 . ?
C14_2 C15_2 1.390(17) . ?
C14_2 C19_2 1.369(16) . ?
C15_2 H15_2 0.9500 . ?
C15_2 C16_2 1.375(16) . ?
C16_2 H16_2 0.9500 . ?
C16_2 C17_2 1.373(17) . ?
C17_2 C18_2 1.406(18) . ?
C18_2 H18_2 0.9500 . ?
C18_2 C19_2 1.373(16) . ?
C19_2 H19_2 0.9500 . ?
Br1_3 Mn1_3 2.519(2) . ?
Mn1_3 N1_3 2.095(9) . ?
Mn1_3 N2_3 2.051(8) . ?
Mn1_3 C1_3 1.804(13) . ?
Mn1_3 C2_3 1.800(12) . ?
Mn1_3 C3_3 1.841(12) . ?
O1_3 C1_3 1.144(15) . ?
O2_3 C2_3 1.155(14) . ?
O3_3 C3_3 1.125(15) . ?
O4_3 N3_3 1.234(15) . ?
O5_3 N3_3 1.229(15) . ?
N1_3 C4_3 1.378(14) . ?
N1_3 C12_3 1.322(13) . ?
N2_3 C13_3 1.291(13) . ?
N2_3 C14_3 1.425(13) . ?
N3_3 C17_3 1.476(15) . ?
C4_3 C5_3 1.400(15) . ?
C4_3 C9_3 1.439(13) . ?
C5_3 H5_3 0.9500 . ?
C5_3 C6_3 1.360(16) . ?
C6_3 H6_3 0.9500 . ?
C6_3 C7_3 1.431(16) . ?
C7_3 H7_3 0.9500 . ?
C7_3 C8_3 1.351(17) . ?
C8_3 H8_3 0.9500 . ?
C8_3 C9_3 1.421(15) . ?
C9_3 C10_3 1.390(15) . ?
C10_3 H10_3 0.9500 . ?
C10_3 C11_3 1.389(15) . ?
C11_3 H11_3 0.9500 . ?
C11_3 C12_3 1.387(14) . ?
C12_3 C13_3 1.454(15) . ?
C13_3 H13_3 0.9500 . ?
C14_3 C15_3 1.373(16) . ?
C14_3 C19_3 1.403(14) . ?
C15_3 H15_3 0.9500 . ?
C15_3 C16_3 1.392(16) . ?
C16_3 H16_3 0.9500 . ?
C16_3 C17_3 1.366(17) . ?
C17_3 C18_3 1.409(18) . ?
C18_3 H18_3 0.9500 . ?
C18_3 C19_3 1.379(16) . ?
C19_3 H19_3 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
N1 Mn1 Br1 88.0(2) . . ?
N2 Mn1 Br1 84.6(2) . . ?
N2 Mn1 N1 78.9(3) . . ?
C1 Mn1 Br1 178.0(3) . . ?
C1 Mn1 N1 91.8(4) . . ?
C1 Mn1 N2 97.3(4) . . ?
C1 Mn1 C2 91.6(4) . . ?
C1 Mn1 C3 93.6(5) . . ?
C2 Mn1 Br1 88.8(3) . . ?
C2 Mn1 N1 174.8(4) . . ?
C2 Mn1 N2 96.7(4) . . ?
C2 Mn1 C3 85.9(4) . . ?
C3 Mn1 Br1 84.4(4) . . ?
C3 Mn1 N1 97.9(3) . . ?
C3 Mn1 N2 168.7(5) . . ?
C4 N1 Mn1 130.8(6) . . ?
C12 N1 Mn1 110.9(6) . . ?
C12 N1 C4 118.2(7) . . ?
C13 N2 Mn1 113.3(7) . . ?
C13 N2 C14 120.3(9) . . ?
C14 N2 Mn1 125.4(6) . . ?
O4 N3 O5 123.8(10) . . ?
O4 N3 C17 118.7(12) . . ?
O5 N3 C17 117.5(11) . . ?
O1 C1 Mn1 176.5(10) . . ?
O2 C2 Mn1 176.3(9) . . ?
O3 C3 Mn1 175.2(10) . . ?
N1 C4 C5 120.3(8) . . ?
N1 C4 C9 121.1(9) . . ?
C5 C4 C9 118.4(9) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.6(9) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.2(10) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 120.2 . . ?
C8 C7 C6 119.5(10) . . ?
C8 C7 H7 120.2 . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.3(9) . . ?
C9 C8 H8 119.4 . . ?
C4 C9 C10 117.9(9) . . ?
C8 C9 C4 119.8(10) . . ?
C8 C9 C10 122.3(9) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.4(8) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.0(9) . . ?
C12 C11 H11 120.0 . . ?
N1 C12 C11 122.5(9) . . ?
N1 C12 C13 114.4(8) . . ?
C11 C12 C13 123.0(9) . . ?
N2 C13 C12 118.3(8) . . ?
N2 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
C15 C14 N2 120.2(9) . . ?
C19 C14 N2 120.3(9) . . ?
C19 C14 C15 119.5(9) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 C14 119.3(10) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.5(11) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 N3 119.6(11) . . ?
C16 C17 C18 122.5(10) . . ?
C18 C17 N3 117.8(11) . . ?
C17 C18 H18 121.2 . . ?
C19 C18 C17 117.5(10) . . ?
C19 C18 H18 121.2 . . ?
C14 C19 C18 121.6(11) . . ?
C14 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
N1_1 Mn1_1 Br1_1 90.8(2) . . ?
N2_1 Mn1_1 Br1_1 84.3(2) . . ?
N2_1 Mn1_1 N1_1 78.4(3) . . ?
C1_1 Mn1_1 Br1_1 176.7(4) . . ?
C1_1 Mn1_1 N1_1 91.7(4) . . ?
C1_1 Mn1_1 N2_1 98.3(4) . . ?
C1_1 Mn1_1 C2_1 91.4(5) . . ?
C1_1 Mn1_1 C3_1 94.3(5) . . ?
C2_1 Mn1_1 Br1_1 86.2(3) . . ?
C2_1 Mn1_1 N1_1 174.8(4) . . ?
C2_1 Mn1_1 N2_1 97.0(4) . . ?
C2_1 Mn1_1 C3_1 86.4(5) . . ?
C3_1 Mn1_1 Br1_1 83.2(4) . . ?
C3_1 Mn1_1 N1_1 97.5(4) . . ?
C3_1 Mn1_1 N2_1 166.8(4) . . ?
C4_1 N1_1 Mn1_1 130.9(7) . . ?
C12_1 N1_1 Mn1_1 112.6(7) . . ?
C12_1 N1_1 C4_1 116.5(9) . . ?
C13_1 N2_1 Mn1_1 115.4(7) . . ?
C13_1 N2_1 C14_1 116.4(8) . . ?
C14_1 N2_1 Mn1_1 126.9(6) . . ?
O4_1 N3_1 O5_1 125.5(10) . . ?
O4_1 N3_1 C17_1 118.6(10) . . ?
O5_1 N3_1 C17_1 115.9(9) . . ?
O1_1 C1_1 Mn1_1 177.6(11) . . ?
O2_1 C2_1 Mn1_1 176.5(10) . . ?
O3_1 C3_1 Mn1_1 176.2(11) . . ?
N1_1 C4_1 C5_1 120.4(9) . . ?
N1_1 C4_1 C9_1 120.7(9) . . ?
C9_1 C4_1 C5_1 118.9(9) . . ?
C4_1 C5_1 H5_1 119.9 . . ?
C6_1 C5_1 C4_1 120.2(10) . . ?
C6_1 C5_1 H5_1 119.9 . . ?
C5_1 C6_1 H6_1 119.5 . . ?
C5_1 C6_1 C7_1 121.1(11) . . ?
C7_1 C6_1 H6_1 119.5 . . ?
C6_1 C7_1 H7_1 119.4 . . ?
C8_1 C7_1 C6_1 121.3(11) . . ?
C8_1 C7_1 H7_1 119.4 . . ?
C7_1 C8_1 H8_1 119.9 . . ?
C7_1 C8_1 C9_1 120.1(10) . . ?
C9_1 C8_1 H8_1 119.9 . . ?
C4_1 C9_1 C8_1 118.3(9) . . ?
C10_1 C9_1 C4_1 119.9(9) . . ?
C10_1 C9_1 C8_1 121.5(9) . . ?
C9_1 C10_1 H10_1 120.7 . . ?
C11_1 C10_1 C9_1 118.6(9) . . ?
C11_1 C10_1 H10_1 120.7 . . ?
C10_1 C11_1 H11_1 120.7 . . ?
C10_1 C11_1 C12_1 118.7(9) . . ?
C12_1 C11_1 H11_1 120.7 . . ?
N1_1 C12_1 C11_1 124.8(10) . . ?
N1_1 C12_1 C13_1 114.2(9) . . ?
C11_1 C12_1 C13_1 120.8(9) . . ?
N2_1 C13_1 C12_1 115.7(9) . . ?
N2_1 C13_1 H13_1 122.2 . . ?
C12_1 C13_1 H13_1 122.2 . . ?
C15_1 C14_1 N2_1 121.6(8) . . ?
C15_1 C14_1 C19_1 119.7(9) . . ?
C19_1 C14_1 N2_1 118.7(9) . . ?
C14_1 C15_1 H15_1 120.0 . . ?
C16_1 C15_1 C14_1 120.0(10) . . ?
C16_1 C15_1 H15_1 120.0 . . ?
C15_1 C16_1 H16_1 120.4 . . ?
C15_1 C16_1 C17_1 119.3(11) . . ?
C17_1 C16_1 H16_1 120.4 . . ?
C16_1 C17_1 N3_1 119.2(11) . . ?
C16_1 C17_1 C18_1 122.4(10) . . ?
C18_1 C17_1 N3_1 118.4(9) . . ?
C17_1 C18_1 H18_1 120.8 . . ?
C19_1 C18_1 C17_1 118.4(9) . . ?
C19_1 C18_1 H18_1 120.8 . . ?
C14_1 C19_1 H19_1 119.8 . . ?
C18_1 C19_1 C14_1 120.3(10) . . ?
C18_1 C19_1 H19_1 119.8 . . ?
N1_2 Mn1_2 Br1_2 88.6(3) . . ?
N2_2 Mn1_2 Br1_2 86.0(2) . . ?
N2_2 Mn1_2 N1_2 78.2(3) . . ?
C1_2 Mn1_2 Br1_2 177.0(3) . . ?
C1_2 Mn1_2 N1_2 93.0(4) . . ?
C1_2 Mn1_2 N2_2 96.8(4) . . ?
C1_2 Mn1_2 C2_2 91.3(5) . . ?
C1_2 Mn1_2 C3_2 91.8(5) . . ?
C2_2 Mn1_2 Br1_2 87.3(4) . . ?
C2_2 Mn1_2 N1_2 173.4(4) . . ?
C2_2 Mn1_2 N2_2 96.2(4) . . ?
C3_2 Mn1_2 Br1_2 85.5(4) . . ?
C3_2 Mn1_2 N1_2 98.7(4) . . ?
C3_2 Mn1_2 N2_2 171.0(5) . . ?
C3_2 Mn1_2 C2_2 86.2(5) . . ?
C4_2 N1_2 Mn1_2 130.6(7) . . ?
C12_2 N1_2 Mn1_2 111.7(6) . . ?
C12_2 N1_2 C4_2 117.1(8) . . ?
C13_2 N2_2 Mn1_2 113.8(7) . . ?
C13_2 N2_2 C14_2 119.1(9) . . ?
C14_2 N2_2 Mn1_2 126.7(6) . . ?
O4_2 N3_2 O5_2 124.3(11) . . ?
O4_2 N3_2 C17_2 118.5(12) . . ?
O5_2 N3_2 C17_2 117.1(11) . . ?
O1_2 C1_2 Mn1_2 179.2(9) . . ?
O2_2 C2_2 Mn1_2 177.6(10) . . ?
O3_2 C3_2 Mn1_2 175.5(10) . . ?
N1_2 C4_2 C5_2 119.6(8) . . ?
N1_2 C4_2 C9_2 121.8(10) . . ?
C5_2 C4_2 C9_2 118.5(10) . . ?
C4_2 C5_2 H5_2 119.5 . . ?
C6_2 C5_2 C4_2 121.0(9) . . ?
C6_2 C5_2 H5_2 119.5 . . ?
C5_2 C6_2 H6_2 120.1 . . ?
C5_2 C6_2 C7_2 119.8(11) . . ?
C7_2 C6_2 H6_2 120.1 . . ?
C6_2 C7_2 H7_2 119.8 . . ?
C8_2 C7_2 C6_2 120.3(11) . . ?
C8_2 C7_2 H7_2 119.8 . . ?
C7_2 C8_2 H8_2 119.5 . . ?
C7_2 C8_2 C9_2 121.0(10) . . ?
C9_2 C8_2 H8_2 119.5 . . ?
C8_2 C9_2 C4_2 119.2(11) . . ?
C10_2 C9_2 C4_2 118.6(10) . . ?
C10_2 C9_2 C8_2 122.0(10) . . ?
C9_2 C10_2 H10_2 120.3 . . ?
C11_2 C10_2 C9_2 119.4(9) . . ?
C11_2 C10_2 H10_2 120.3 . . ?
C10_2 C11_2 H11_2 120.7 . . ?
C10_2 C11_2 C12_2 118.6(10) . . ?
C12_2 C11_2 H11_2 120.7 . . ?
N1_2 C12_2 C11_2 123.8(10) . . ?
N1_2 C12_2 C13_2 114.2(8) . . ?
C11_2 C12_2 C13_2 122.0(9) . . ?
N2_2 C13_2 C12_2 118.8(9) . . ?
N2_2 C13_2 H13_2 120.6 . . ?
C12_2 C13_2 H13_2 120.6 . . ?
C15_2 C14_2 N2_2 121.2(10) . . ?
C19_2 C14_2 N2_2 118.5(10) . . ?
C19_2 C14_2 C15_2 120.3(10) . . ?
C14_2 C15_2 H15_2 120.0 . . ?
C16_2 C15_2 C14_2 119.9(11) . . ?
C16_2 C15_2 H15_2 120.0 . . ?
C15_2 C16_2 H16_2 120.3 . . ?
C17_2 C16_2 C15_2 119.4(11) . . ?
C17_2 C16_2 H16_2 120.3 . . ?
C16_2 C17_2 N3_2 120.0(11) . . ?
C16_2 C17_2 C18_2 121.1(10) . . ?
C18_2 C17_2 N3_2 118.9(11) . . ?
C17_2 C18_2 H18_2 120.8 . . ?
C19_2 C18_2 C17_2 118.3(12) . . ?
C19_2 C18_2 H18_2 120.8 . . ?
C14_2 C19_2 C18_2 120.9(12) . . ?
C14_2 C19_2 H19_2 119.6 . . ?
C18_2 C19_2 H19_2 119.6 . . ?
N1_3 Mn1_3 Br1_3 86.0(2) . . ?
N2_3 Mn1_3 Br1_3 87.2(2) . . ?
N2_3 Mn1_3 N1_3 78.4(3) . . ?
C1_3 Mn1_3 Br1_3 176.6(4) . . ?
C1_3 Mn1_3 N1_3 91.9(4) . . ?
C1_3 Mn1_3 N2_3 94.9(4) . . ?
C1_3 Mn1_3 C3_3 91.5(6) . . ?
C2_3 Mn1_3 Br1_3 89.1(3) . . ?
C2_3 Mn1_3 N1_3 172.1(5) . . ?
C2_3 Mn1_3 N2_3 95.2(4) . . ?
C2_3 Mn1_3 C1_3 93.3(5) . . ?
C2_3 Mn1_3 C3_3 84.7(6) . . ?
C3_3 Mn1_3 Br1_3 86.4(5) . . ?
C3_3 Mn1_3 N1_3 101.1(5) . . ?
C3_3 Mn1_3 N2_3 173.6(5) . . ?
C4_3 N1_3 Mn1_3 129.4(7) . . ?
C12_3 N1_3 Mn1_3 113.3(7) . . ?
C12_3 N1_3 C4_3 117.0(9) . . ?
C13_3 N2_3 Mn1_3 113.4(7) . . ?
C13_3 N2_3 C14_3 118.7(9) . . ?
C14_3 N2_3 Mn1_3 127.5(7) . . ?
O4_3 N3_3 C17_3 118.8(12) . . ?
O5_3 N3_3 O4_3 125.8(12) . . ?
O5_3 N3_3 C17_3 115.5(11) . . ?
O1_3 C1_3 Mn1_3 179.0(10) . . ?
O2_3 C2_3 Mn1_3 176.1(11) . . ?
O3_3 C3_3 Mn1_3 173.7(13) . . ?
N1_3 C4_3 C5_3 121.6(9) . . ?
N1_3 C4_3 C9_3 120.0(9) . . ?
C5_3 C4_3 C9_3 118.4(9) . . ?
C4_3 C5_3 H5_3 119.3 . . ?
C6_3 C5_3 C4_3 121.4(10) . . ?
C6_3 C5_3 H5_3 119.3 . . ?
C5_3 C6_3 H6_3 119.9 . . ?
C5_3 C6_3 C7_3 120.3(10) . . ?
C7_3 C6_3 H6_3 119.9 . . ?
C6_3 C7_3 H7_3 120.0 . . ?
C8_3 C7_3 C6_3 120.0(10) . . ?
C8_3 C7_3 H7_3 120.0 . . ?
C7_3 C8_3 H8_3 119.6 . . ?
C7_3 C8_3 C9_3 120.8(10) . . ?
C9_3 C8_3 H8_3 119.6 . . ?
C8_3 C9_3 C4_3 118.9(9) . . ?
C10_3 C9_3 C4_3 119.6(9) . . ?
C10_3 C9_3 C8_3 121.4(9) . . ?
C9_3 C10_3 H10_3 120.6 . . ?
C11_3 C10_3 C9_3 118.9(9) . . ?
C11_3 C10_3 H10_3 120.6 . . ?
C10_3 C11_3 H11_3 121.1 . . ?
C12_3 C11_3 C10_3 117.7(10) . . ?
C12_3 C11_3 H11_3 121.1 . . ?
N1_3 C12_3 C11_3 126.2(10) . . ?
N1_3 C12_3 C13_3 114.1(9) . . ?
C11_3 C12_3 C13_3 119.7(9) . . ?
N2_3 C13_3 C12_3 119.0(10) . . ?
N2_3 C13_3 H13_3 120.5 . . ?
C12_3 C13_3 H13_3 120.5 . . ?
C15_3 C14_3 N2_3 122.5(9) . . ?
C15_3 C14_3 C19_3 120.4(10) . . ?
C19_3 C14_3 N2_3 117.1(10) . . ?
C14_3 C15_3 H15_3 119.7 . . ?
C14_3 C15_3 C16_3 120.5(10) . . ?
C16_3 C15_3 H15_3 119.7 . . ?
C15_3 C16_3 H16_3 120.9 . . ?
C17_3 C16_3 C15_3 118.2(11) . . ?
C17_3 C16_3 H16_3 120.9 . . ?
C16_3 C17_3 N3_3 119.7(12) . . ?
C16_3 C17_3 C18_3 123.1(10) . . ?
C18_3 C17_3 N3_3 117.2(10) . . ?
C17_3 C18_3 H18_3 121.3 . . ?
C19_3 C18_3 C17_3 117.4(10) . . ?
C19_3 C18_3 H18_3 121.3 . . ?
C14_3 C19_3 H19_3 119.9 . . ?
C18_3 C19_3 C14_3 120.3(11) . . ?
C18_3 C19_3 H19_3 119.9 . . ?

_olex2_date_sample_data_collection 2020-02-20
_olex2_date_sample_submission    2019-12-01
_olex2_exptl_crystal_mounting_method 
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide microloop (MicroMounts of MiTeGen) and transferred to stream of cold 
nitrogen (Oxford Cryostream 800).
;
_olex2_submission_original_sample_id R/Q-NO2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_diffrn_reflns_filtered   17164
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.202
_oxdiff_exptl_absorpt_empirical_full_min 0.301
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9946(5)
2 0.0054(5)

_chemical_properties_physical    Moisture-sensitive,Light-sensitive
####################################################################### 
# 
# 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_cmpd_9
_database_code_depnum_ccdc_archive 'CCDC 1999562'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich '
;Institute of Inorganic Chemistry, Wuerzburg University, Am Hubland, Wuerzburg, Germany
Germany
;
_audit_update_record             
;
2020-04-27 deposited with the CCDC.	2020-06-09 downloaded from the CCDC.
;

_audit_creation_date             2020-02-27
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3


_chemical_formula_moiety         'C15 H9 Br Cl Mn N2 O3'
_chemical_formula_sum            'C15 H9 Br Cl Mn N2 O3'
_chemical_formula_weight         435.54

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'
Cl Cl 0.1484 0.1585 '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'

_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                   8.9142(19)
_cell_length_b                   26.172(7)
_cell_length_c                   6.8978(18)
_cell_angle_alpha                90
_cell_angle_beta                 109.071(7)
_cell_angle_gamma                90
_cell_volume                     1521.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9897
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      28.26
_cell_special_details            
;
To simulate systematic errors the final estimation of uncertainties
in unit cell parameters was based on 32 Monte-Carlo simulations.
;

_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide microloop (MicroMounts of MiTeGen) and transferred to stream of cold 
nitrogen (Bruker Kryoflex2).
;
_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.902
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.333
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.206
_exptl_absorpt_coefficient_mu    3.685
_shelx_estimated_absorpt_T_min   0.373
_shelx_estimated_absorpt_T_max   0.517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.500066
_exptl_absorpt_correction_T_max  0.745685
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2.00 -3.00 0.00 0.1130
-2.00 3.00 0.00 0.0470
-2.00 -2.00 3.00 0.1600
2.00 2.00 -3.00 0.1130
1.00 -1.00 -2.00 0.1250
0.00 -1.00 0.00 0.1470
0.00 1.00 0.00 0.1620
-2.00 3.00 3.00 0.1750
1.00 0.00 -1.00 0.1250
-1.00 -3.00 0.00 0.0800
1.00 3.00 0.00 0.1340
-1.00 1.00 3.00 0.1670
2.00 3.00 0.00 0.1120
-2.00 -3.00 0.00 0.0580
-1.00 -1.00 3.00 0.1600
3.00 2.00 0.00 0.1030
-3.00 -1.00 0.00 0.0370
-1.00 3.00 1.00 0.1700

_exptl_absorpt_process_details   'TwinAbs 2012/ (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_source                   'rotating-anode (Nonius FR-591)'
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'CCD area detector (Apex2)'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            3773
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.417
_diffrn_reflns_theta_max         28.280
_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             3773
_reflns_number_gt                3241
_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       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.40A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.40A (Bruker AXS)'
_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          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and 
goodness of fit S are based on F², conventional R-factors R are based on F, 
with F set to zero for negative F². The threshold expression of F² > 
2sigma(F²) is used only for calculating R-factors(gt) etc. and is not 
relevant to the choice of reflections for refinement.  R-factors based on F² 
are statistically about twice as large as those based on F, and R-factors 
based on ALL data will be even larger.
The crystal was a non-merohedral twin with component 2 rotated by 180.0°
around [-0.001 -0.001 1.000] (reciprocal) or [0.425 0.000 1.000] (direct) 
axis. Only reflections of the larger domain were used in the refinement.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0161P)²+1.9991P] 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         3773
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_ref         0.0560
_refine_ls_wR_factor_gt          0.0534
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.003
_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 0.26267(3) 0.58013(2) 0.25164(3) 0.01293(6) Uani 1 1 d . . . . .
Mn1 Mn 0.37649(4) 0.61287(2) 0.61517(5) 0.00863(8) Uani 1 1 d . . . . .
Cl1 Cl -0.16402(7) 0.83421(2) 0.38805(9) 0.01536(12) Uani 1 1 d . . . . .
O1 O 0.5083(2) 0.65960(6) 1.0250(3) 0.0174(4) Uani 1 1 d . . . . .
O2 O 0.4709(2) 0.70595(6) 0.4402(3) 0.0196(4) Uani 1 1 d . . . . .
O3 O 0.68836(19) 0.56983(6) 0.6434(3) 0.0182(4) Uani 1 1 d . . . . .
N1 N 0.2977(2) 0.54666(7) 0.7066(3) 0.0100(4) Uani 1 1 d . . . . .
N2 N 0.1506(2) 0.63343(7) 0.6023(3) 0.0085(4) Uani 1 1 d . . . . .
C1 C 0.4561(3) 0.64022(8) 0.8690(4) 0.0117(5) Uani 1 1 d . . . . .
C2 C 0.4303(3) 0.67060(8) 0.5066(4) 0.0124(4) Uani 1 1 d . . . . .
C3 C 0.5663(3) 0.58641(8) 0.6305(3) 0.0121(4) Uani 1 1 d . . . . .
C4 C 0.3744(3) 0.50207(8) 0.7547(3) 0.0130(5) Uani 1 1 d . . . . .
H4 H 0.479953 0.499700 0.751565 0.016 Uiso 1 1 calc R U . . .
C5 C 0.3057(3) 0.45912(8) 0.8092(4) 0.0161(5) Uani 1 1 d . . . . .
H5 H 0.363814 0.428097 0.842139 0.019 Uiso 1 1 calc R U . . .
C6 C 0.1527(3) 0.46166(9) 0.8153(4) 0.0154(5) Uani 1 1 d . . . . .
H6 H 0.104601 0.432700 0.853653 0.019 Uiso 1 1 calc R U . . .
C7 C 0.0709(3) 0.50736(8) 0.7644(3) 0.0127(5) Uani 1 1 d . . . . .
H7 H -0.034884 0.510357 0.766119 0.015 Uiso 1 1 calc R U . . .
C8 C 0.1466(3) 0.54861(8) 0.7108(3) 0.0103(4) Uani 1 1 d . . . . .
C9 C 0.0706(3) 0.59762(8) 0.6521(3) 0.0109(4) Uani 1 1 d . . . . .
H9 H -0.035068 0.603300 0.650352 0.013 Uiso 1 1 calc R U . . .
C10 C 0.0738(3) 0.68184(8) 0.5433(3) 0.0096(4) Uani 1 1 d . . . . .
C11 C -0.0845(3) 0.68433(8) 0.4219(3) 0.0112(4) Uani 1 1 d . . . . .
H11 H -0.142102 0.653837 0.372458 0.013 Uiso 1 1 calc R U . . .
C12 C -0.1584(3) 0.73146(8) 0.3730(3) 0.0121(4) Uani 1 1 d . . . . .
H12 H -0.266966 0.733584 0.290852 0.015 Uiso 1 1 calc R U . . .
C13 C -0.0718(3) 0.77525(8) 0.4455(3) 0.0111(4) Uani 1 1 d . . . . .
C14 C 0.0876(3) 0.77354(8) 0.5641(3) 0.0120(4) Uani 1 1 d . . . . .
H14 H 0.145637 0.804121 0.610672 0.014 Uiso 1 1 calc R U . . .
C15 C 0.1602(3) 0.72627(8) 0.6132(3) 0.0105(4) Uani 1 1 d . . . . .
H15 H 0.268955 0.724202 0.694614 0.013 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
Br1 Mn1 2.5276(7) . ?
Mn1 C3 1.799(2) . ?
Mn1 C1 1.808(2) . ?
Mn1 C2 1.819(2) . ?
Mn1 N1 2.0455(19) . ?
Mn1 N2 2.0582(18) . ?
Cl1 C13 1.733(2) . ?
O1 C1 1.142(3) . ?
O2 C2 1.143(3) . ?
O3 C3 1.147(3) . ?
N1 C4 1.338(3) . ?
N1 C8 1.358(3) . ?
N2 C9 1.290(3) . ?
N2 C10 1.434(3) . ?
C4 C5 1.390(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.379(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.385(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.386(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.445(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.387(3) . ?
C10 C15 1.391(3) . ?
C11 C12 1.387(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.381(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(3) . ?
C14 C15 1.386(3) . ?
C14 H14 0.9500 . ?
C15 H15 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 C1 91.81(10) . . ?
C3 Mn1 C2 88.54(10) . . ?
C1 Mn1 C2 89.83(10) . . ?
C3 Mn1 N1 93.84(9) . . ?
C1 Mn1 N1 95.88(9) . . ?
C2 Mn1 N1 173.73(9) . . ?
C3 Mn1 N2 172.45(9) . . ?
C1 Mn1 N2 90.41(8) . . ?
C2 Mn1 N2 98.68(8) . . ?
N1 Mn1 N2 78.76(7) . . ?
C3 Mn1 Br1 89.58(7) . . ?
C1 Mn1 Br1 176.50(7) . . ?
C2 Mn1 Br1 86.99(7) . . ?
N1 Mn1 Br1 87.23(5) . . ?
N2 Mn1 Br1 88.61(5) . . ?
C4 N1 C8 117.25(19) . . ?
C4 N1 Mn1 128.02(16) . . ?
C8 N1 Mn1 114.69(14) . . ?
C9 N2 C10 117.62(18) . . ?
C9 N2 Mn1 114.61(15) . . ?
C10 N2 Mn1 127.77(14) . . ?
O1 C1 Mn1 176.6(2) . . ?
O2 C2 Mn1 176.8(2) . . ?
O3 C3 Mn1 178.9(2) . . ?
N1 C4 C5 122.5(2) . . ?
N1 C4 H4 118.7 . . ?
C5 C4 H4 118.7 . . ?
C6 C5 C4 119.8(2) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 118.5(2) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
C6 C7 C8 118.6(2) . . ?
C6 C7 H7 120.7 . . ?
C8 C7 H7 120.7 . . ?
N1 C8 C7 123.3(2) . . ?
N1 C8 C9 113.88(19) . . ?
C7 C8 C9 122.8(2) . . ?
N2 C9 C8 118.1(2) . . ?
N2 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
C11 C10 C15 120.6(2) . . ?
C11 C10 N2 120.63(19) . . ?
C15 C10 N2 118.78(19) . . ?
C12 C11 C10 119.8(2) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C13 C12 C11 119.0(2) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C12 C13 C14 122.0(2) . . ?
C12 C13 Cl1 119.27(17) . . ?
C14 C13 Cl1 118.75(17) . . ?
C15 C14 C13 118.6(2) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C14 C15 C10 120.0(2) . . ?
C14 C15 H15 120.0 . . ?
C10 C15 H15 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
C8 N1 C4 C5 -0.6(3) . . . . ?
Mn1 N1 C4 C5 -178.03(17) . . . . ?
N1 C4 C5 C6 -0.1(4) . . . . ?
C4 C5 C6 C7 0.6(3) . . . . ?
C5 C6 C7 C8 -0.4(3) . . . . ?
C4 N1 C8 C7 0.9(3) . . . . ?
Mn1 N1 C8 C7 178.62(17) . . . . ?
C4 N1 C8 C9 -178.56(19) . . . . ?
Mn1 N1 C8 C9 -0.8(2) . . . . ?
C6 C7 C8 N1 -0.4(3) . . . . ?
C6 C7 C8 C9 179.0(2) . . . . ?
C10 N2 C9 C8 179.68(19) . . . . ?
Mn1 N2 C9 C8 0.3(3) . . . . ?
N1 C8 C9 N2 0.3(3) . . . . ?
C7 C8 C9 N2 -179.1(2) . . . . ?
C9 N2 C10 C11 -40.1(3) . . . . ?
Mn1 N2 C10 C11 139.13(18) . . . . ?
C9 N2 C10 C15 138.6(2) . . . . ?
Mn1 N2 C10 C15 -42.1(3) . . . . ?
C15 C10 C11 C12 -1.3(3) . . . . ?
N2 C10 C11 C12 177.5(2) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
C11 C12 C13 C14 0.7(3) . . . . ?
C11 C12 C13 Cl1 -179.08(17) . . . . ?
C12 C13 C14 C15 -1.0(3) . . . . ?
Cl1 C13 C14 C15 178.72(17) . . . . ?
C13 C14 C15 C10 0.2(3) . . . . ?
C11 C10 C15 C14 0.9(3) . . . . ?
N2 C10 C15 C14 -177.9(2) . . . . ?

_refine_diff_density_max         0.507
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.102


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Light-sensitive
####################################################################### 
# 
# 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_cmpd_7
_database_code_depnum_ccdc_archive 'CCDC 1999561'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich '
;Institute of Inorganic Chemistry, Wuerzburg University, Am Hubland, Wuerzburg, Germany
Germany
;
_audit_update_record             
;
2020-04-27 deposited with the CCDC.	2020-06-09 downloaded from the CCDC.
;

_audit_creation_date             2020-02-21
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3


_chemical_formula_moiety         'C15 H10 Br Mn N2 O4'
_chemical_formula_sum            'C15 H10 Br Mn N2 O4'
_chemical_formula_weight         417.10

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'

_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                   8.7327(17)
_cell_length_b                   26.447(10)
_cell_length_c                   7.0400(14)
_cell_angle_alpha                90
_cell_angle_beta                 113.752(17)
_cell_angle_gamma                90
_cell_volume                     1488.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7897
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      28.26


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide microloop (MicroMounts of MiTeGen) and transferred to stream of cold 
nitrogen (Oxford Cryostream 700).
;
_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.862
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.496
_exptl_crystal_size_mid          0.281
_exptl_crystal_size_min          0.228
_exptl_absorpt_coefficient_mu    3.593
_shelx_estimated_absorpt_T_min   0.269
_shelx_estimated_absorpt_T_max   0.495
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2887
_exptl_absorpt_correction_T_max  0.4311
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 3.00 0.00 0.1200
1.00 -3.00 0.00 0.1150
2.00 -1.00 -3.00 0.2300
-2.00 1.00 3.00 0.2100
1.00 0.00 0.00 0.1140
-1.00 0.00 0.00 0.0640
3.00 -1.00 1.00 0.2050
-1.00 -2.00 0.00 0.1190
-3.00 1.00 -1.00 0.2250
1.00 3.00 0.00 0.1550
3.00 2.00 1.00 0.2100
-3.00 -2.00 -1.00 0.1920
3.00 -3.00 2.00 0.2140
3.00 0.00 2.00 0.2150
-3.00 0.00 -2.00 0.2380
-3.00 -3.00 -2.00 0.2010
2.00 -3.00 -1.00 0.1610
-1.00 -3.00 2.00 0.2150
3.00 0.00 -2.00 0.2230
2.00 -3.00 0.00 0.1100
1.00 -1.00 0.00 0.1050
3.00 -1.00 0.00 0.1100

_exptl_absorpt_process_details   'SadAbs 2016/2 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_source                   'rotating-anode (Nonius FR-591)'
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'CCD area detector (Apex2)'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            23510
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.540
_diffrn_reflns_theta_max         28.283
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3705
_reflns_number_gt                3298
_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       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.40A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.40A (Bruker AXS)'
_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          
;

 Refinement of F² against ALL reflections. The weighted R-factor wR and 
goodness of fit S are based on F², conventional R-factors R are based on F, 
with F set to zero for negative F². The threshold expression of F² > 
2sigma(F²) is used only for calculating R-factors(gt) etc. and is not 
relevant to the choice of reflections for refinement. R-factors based on F² 
are statistically about twice as large as those based on F, and R-factors 
based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0202P)²+1.2350P] 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         3705
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0241
_refine_ls_wR_factor_ref         0.0528
_refine_ls_wR_factor_gt          0.0512
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 0.74476(2) 0.41465(2) -0.00506(3) 0.01325(5) Uani 1 1 d . . . . .
C1 C 0.4875(2) 0.35987(7) 0.3724(3) 0.0141(4) Uani 1 1 d . . . . .
N1 N 0.67474(18) 0.45012(6) 0.3784(2) 0.0113(3) Uani 1 1 d . . . . .
O1 O 0.42292(18) 0.34225(5) 0.4670(2) 0.0206(3) Uani 1 1 d . . . . .
Mn1 Mn 0.58942(3) 0.38506(2) 0.21401(4) 0.00980(7) Uani 1 1 d . . . . .
O2 O 0.47298(17) 0.29497(5) -0.0567(2) 0.0200(3) Uani 1 1 d . . . . .
C2 C 0.5253(2) 0.32870(7) 0.0521(3) 0.0135(4) Uani 1 1 d . . . . .
N2 N 0.81755(18) 0.36183(6) 0.4330(2) 0.0104(3) Uani 1 1 d . . . . .
O4 O 1.08217(18) 0.16706(5) 0.5154(2) 0.0204(3) Uani 1 1 d . . . . .
HO4 H 1.010353 0.145954 0.515626 0.031 Uiso 1 1 calc R U . . .
C4 C 0.6006(2) 0.49538(7) 0.3390(3) 0.0150(4) Uani 1 1 d . . . . .
H4 H 0.494114 0.498495 0.226890 0.018 Uiso 1 1 calc R U . . .
O3 O 0.26431(17) 0.42903(6) -0.0586(2) 0.0222(3) Uani 1 1 d . . . . .
C3 C 0.3934(2) 0.41250(7) 0.0443(3) 0.0149(4) Uani 1 1 d . . . . .
C9 C 0.9013(2) 0.39632(7) 0.5623(3) 0.0124(4) Uani 1 1 d . . . . .
H9 H 1.007466 0.389192 0.669713 0.015 Uiso 1 1 calc R U . . .
C8 C 0.8281(2) 0.44643(7) 0.5385(3) 0.0121(4) Uani 1 1 d . . . . .
C7 C 0.9064(2) 0.48745(7) 0.6637(3) 0.0153(4) Uani 1 1 d . . . . .
H7 H 1.012392 0.483608 0.775959 0.018 Uiso 1 1 calc R U . . .
C6 C 0.8270(2) 0.53400(7) 0.6215(3) 0.0163(4) Uani 1 1 d . . . . .
H6 H 0.877171 0.562614 0.704915 0.020 Uiso 1 1 calc R U . . .
C5 C 0.6731(2) 0.53809(7) 0.4556(3) 0.0161(4) Uani 1 1 d . . . . .
H5 H 0.617600 0.569810 0.421747 0.019 Uiso 1 1 calc R U . . .
C10 C 0.8876(2) 0.31229(7) 0.4509(3) 0.0111(3) Uani 1 1 d . . . . .
C11 C 1.0569(2) 0.30475(7) 0.4952(3) 0.0137(4) Uani 1 1 d . . . . .
H11 H 1.128420 0.332983 0.511823 0.016 Uiso 1 1 calc R U . . .
C12 C 1.1206(2) 0.25606(8) 0.5148(3) 0.0159(4) Uani 1 1 d . . . . .
H12 H 1.235555 0.250865 0.544032 0.019 Uiso 1 1 calc R U . . .
C13 C 1.0156(2) 0.21496(7) 0.4915(3) 0.0148(4) Uani 1 1 d . . . . .
C14 C 0.8470(2) 0.22233(7) 0.4445(3) 0.0144(4) Uani 1 1 d . . . . .
H14 H 0.775391 0.194057 0.426352 0.017 Uiso 1 1 calc R U . . .
C15 C 0.7833(2) 0.27072(7) 0.4240(3) 0.0128(4) Uani 1 1 d . . . . .
H15 H 0.667665 0.275666 0.391423 0.015 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
Br1 Mn1 2.5527(5) . ?
C1 O1 1.132(2) . ?
C1 Mn1 1.811(2) . ?
N1 C4 1.336(2) . ?
N1 C8 1.363(2) . ?
N1 Mn1 2.0397(17) . ?
Mn1 C3 1.799(2) . ?
Mn1 C2 1.822(2) . ?
Mn1 N2 2.0612(16) . ?
O2 C2 1.144(2) . ?
N2 C9 1.288(2) . ?
N2 C10 1.430(2) . ?
O4 C13 1.376(2) . ?
O4 HO4 0.8400 . ?
C4 C5 1.390(3) . ?
C4 H4 0.9500 . ?
O3 C3 1.153(2) . ?
C9 C8 1.451(3) . ?
C9 H9 0.9500 . ?
C8 C7 1.391(3) . ?
C7 C6 1.385(3) . ?
C7 H7 0.9500 . ?
C6 C5 1.384(3) . ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?
C10 C15 1.391(3) . ?
C10 C11 1.397(3) . ?
C11 C12 1.387(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(3) . ?
C14 C15 1.380(3) . ?
C14 H14 0.9500 . ?
C15 H15 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
O1 C1 Mn1 177.09(17) . . ?
C4 N1 C8 117.95(16) . . ?
C4 N1 Mn1 127.02(13) . . ?
C8 N1 Mn1 114.94(12) . . ?
C3 Mn1 C1 89.17(9) . . ?
C3 Mn1 C2 86.80(9) . . ?
C1 Mn1 C2 88.91(8) . . ?
C3 Mn1 N1 93.95(8) . . ?
C1 Mn1 N1 96.81(7) . . ?
C2 Mn1 N1 174.23(7) . . ?
C3 Mn1 N2 172.46(8) . . ?
C1 Mn1 N2 89.80(7) . . ?
C2 Mn1 N2 100.65(8) . . ?
N1 Mn1 N2 78.75(6) . . ?
C3 Mn1 Br1 94.01(6) . . ?
C1 Mn1 Br1 175.90(6) . . ?
C2 Mn1 Br1 88.68(6) . . ?
N1 Mn1 Br1 85.57(4) . . ?
N2 Mn1 Br1 87.39(4) . . ?
O2 C2 Mn1 174.67(17) . . ?
C9 N2 C10 119.05(16) . . ?
C9 N2 Mn1 114.84(13) . . ?
C10 N2 Mn1 126.11(12) . . ?
C13 O4 HO4 109.5 . . ?
N1 C4 C5 122.53(18) . . ?
N1 C4 H4 118.7 . . ?
C5 C4 H4 118.7 . . ?
O3 C3 Mn1 176.66(17) . . ?
N2 C9 C8 117.83(17) . . ?
N2 C9 H9 121.1 . . ?
C8 C9 H9 121.1 . . ?
N1 C8 C7 122.45(17) . . ?
N1 C8 C9 113.64(16) . . ?
C7 C8 C9 123.90(17) . . ?
C6 C7 C8 118.77(18) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
C5 C6 C7 118.83(18) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C6 C5 C4 119.43(18) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C15 C10 C11 119.58(17) . . ?
C15 C10 N2 118.62(16) . . ?
C11 C10 N2 121.80(16) . . ?
C12 C11 C10 120.04(18) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 119.71(17) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
O4 C13 C14 120.95(18) . . ?
O4 C13 C12 118.70(17) . . ?
C14 C13 C12 120.35(18) . . ?
C15 C14 C13 120.02(18) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C10 120.29(17) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?

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
C8 N1 C4 C5 -0.6(3) . . . . ?
Mn1 N1 C4 C5 -176.98(13) . . . . ?
C10 N2 C9 C8 179.18(15) . . . . ?
Mn1 N2 C9 C8 -0.6(2) . . . . ?
C4 N1 C8 C7 1.8(3) . . . . ?
Mn1 N1 C8 C7 178.59(13) . . . . ?
C4 N1 C8 C9 -177.24(15) . . . . ?
Mn1 N1 C8 C9 -0.44(18) . . . . ?
N2 C9 C8 N1 0.7(2) . . . . ?
N2 C9 C8 C7 -178.34(17) . . . . ?
N1 C8 C7 C6 -1.3(3) . . . . ?
C9 C8 C7 C6 177.65(17) . . . . ?
C8 C7 C6 C5 -0.4(3) . . . . ?
C7 C6 C5 C4 1.5(3) . . . . ?
N1 C4 C5 C6 -1.0(3) . . . . ?
C9 N2 C10 C15 138.81(17) . . . . ?
Mn1 N2 C10 C15 -41.5(2) . . . . ?
C9 N2 C10 C11 -41.0(2) . . . . ?
Mn1 N2 C10 C11 138.72(15) . . . . ?
C15 C10 C11 C12 -0.9(3) . . . . ?
N2 C10 C11 C12 178.93(16) . . . . ?
C10 C11 C12 C13 -0.4(3) . . . . ?
C11 C12 C13 O4 -178.78(16) . . . . ?
C11 C12 C13 C14 1.3(3) . . . . ?
O4 C13 C14 C15 179.06(16) . . . . ?
C12 C13 C14 C15 -1.1(3) . . . . ?
C13 C14 C15 C10 -0.2(3) . . . . ?
C11 C10 C15 C14 1.2(3) . . . . ?
N2 C10 C15 C14 -178.65(16) . . . . ?

_refine_diff_density_max         0.472
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.072


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_chemical_compound_source        Methanol
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Light-sensitive
