# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_L1
_database_code_depnum_ccdc_archive 'CCDC 2248092'
loop_
_audit_author_name
_audit_author_address
'Wen-Hua Sun '
;Institute of Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2023-03-13 deposited with the CCDC.	2023-07-11 downloaded from the CCDC.
;
_audit_creation_date             2023-03-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Br), 2(C12 H19 N2)'
_chemical_formula_sum            'C24 H38 Br2 N4'
_chemical_formula_weight         542.40
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     'C H N O Mn Br'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   17.4207(4)
_cell_length_b                   7.60980(10)
_cell_length_c                   19.8264(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.023(2)
_cell_angle_gamma                90
_cell_volume                     2618.25(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8875
_cell_measurement_temperature    169.98(10)
_cell_measurement_theta_max      73.2110
_cell_measurement_theta_min      3.5170
_shelx_estimated_absorpt_T_max   0.923
_shelx_estimated_absorpt_T_min   0.498
_exptl_absorpt_coefficient_mu    4.045
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            21032
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.285
_diffrn_reflns_theta_min         3.240
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  20.00   0.50    0.20    --  -47.57  44.00 121.00   96
  2  ω   -111.00 -37.00   0.50    0.20    --  -47.57 -44.00 -28.00  148
  3  ω     38.00 100.00   0.50    0.20    --   47.57  44.00 121.00  124
  4  ω    -11.00  34.00   0.50    0.20    --   47.57 -44.00 -28.00   90
  5  ω   -164.00 -97.00   0.50    1.00    --  -99.00 -44.00 -28.00  134
  6  ω     91.00 130.00   0.50    1.00    --  103.25  44.00 121.00   78
  7  ω    -20.00  26.00   0.50    0.20    --  -47.57  19.00 -90.00   92
  8  ω   -112.00 -77.00   0.50    0.20    --  -47.57-125.00  60.00   70
  9  ω   -130.00 -85.00   0.50    1.00    --  -99.00 -94.00  90.00   90
 10  ω    -64.00 -27.00   0.50    1.00    --  -99.00  61.00 -60.00   74
 11  ω    -63.00 -27.00   0.50    1.00    --  -99.00  61.00-150.00   72
 12  ω    -67.00 -27.00   0.50    1.00    --  -99.00  61.00 -90.00   80
 13  ω    -55.00 -26.00   0.50    1.00    --  -99.00  61.00  60.00   58
 14  ω   -163.00-133.00   0.50    1.00    --  -99.00 -94.00  90.00   60
 15  ω    -61.00 -26.00   0.50    1.00    --  -99.00  61.00 150.00   70
 16  ω    -68.00 -27.00   0.50    1.00    --  -99.00  61.00 -30.00   82
 17  ω    -66.00 -32.00   0.50    1.00    --  -99.00  61.00 120.00   68
 18  ω     67.00 111.00   0.50    1.00    --  103.25-125.00-120.00   88
 19  ω     32.00  74.00   0.50    1.00    --  103.25 -61.00  90.00   84
 20  ω     32.00  64.00   0.50    1.00    --  103.25 -61.00 -60.00   64
 21  ω     42.00  73.00   0.50    1.00    --  103.25 -61.00   0.00   62
 22  ω    140.00 168.00   0.50    1.00    --  103.25  15.00  60.00   56
 23  ω     31.00  71.00   0.50    1.00    --  103.25 -61.00 -30.00   80
 24  ω    111.00 167.00   0.50    1.00    --  103.25  30.00-180.00  112
 25  ω     89.00 165.00   0.50    1.00    --  103.25  61.00-150.00  152
 26  ω     96.00 122.00   0.50    1.00    --  103.25  15.00  60.00   52
 27  ω     70.00 108.00   0.50    1.00    --  103.25 -77.00  90.00   76
 28  ω     31.00  59.00   0.50    1.00    --  103.25 -77.00  90.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0167236000
_diffrn_orient_matrix_UB_12      -0.0775765000
_diffrn_orient_matrix_UB_13      0.0690201000
_diffrn_orient_matrix_UB_21      0.0811814000
_diffrn_orient_matrix_UB_22      -0.0817615000
_diffrn_orient_matrix_UB_23      0.0078355000
_diffrn_orient_matrix_UB_31      0.0318118000
_diffrn_orient_matrix_UB_32      0.1681519000
_diffrn_orient_matrix_UB_33      0.0354930000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4484
_reflns_number_total             5239
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         1.006
_refine_diff_density_min         -0.823
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         5239
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0511
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0528P)²+5.6904P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1299
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 Br1A
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Uiso/Uaniso restraints and constraints
Uanis(Br1A) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.005
4. Others
 Sof(Br1A)=1-FVAR(1)
 Sof(Br1)=FVAR(1)
 Sof(Br2A)=1-FVAR(2)
 Sof(Br2)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C8(H8), C20(H20), C10(H10), C22(H22)
5.b Secondary CH2 refined with riding coordinates:
 N2(H2a,H2b), N4(H4a,H4b), C7(H7a,H7b), C6(H6a,H6b), C5(H5a,H5b), C19(H19a,
 H19b), C18(H18a,H18b), C17(H17a,H17b)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C15(H15), C1(H1), C14(H14), C13(H13)
5.d Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C11(H11a,H11b,H11c), C23(H23a,H23b,H23c), C24(H24a,H24b,
 H24c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.68492(3) 0.33054(5) 0.10220(2) 0.03417(17) Uani 0.937(3) 1 d . . P A 1
Br2 Br 0.37392(6) 0.69069(6) 0.39488(3) 0.0502(3) Uani 0.929(3) 1 d . . P B 1
N2 N 0.62861(17) 0.7216(4) 0.05019(15) 0.0299(6) Uani 1 1 d . . . . .
H2A H 0.581779 0.727743 0.028436 0.036 Uiso 1 1 calc R U . . .
H2B H 0.635288 0.611635 0.064837 0.036 Uiso 1 1 calc R U . . .
N4 N 0.40671(19) 0.2896(4) 0.44184(15) 0.0340(7) Uani 1 1 d . . . . .
H4A H 0.396582 0.401061 0.430674 0.041 Uiso 1 1 calc R U . . .
H4B H 0.457308 0.281258 0.452292 0.041 Uiso 1 1 calc R U . . .
N3 N 0.51755(19) 0.2446(5) 0.35977(18) 0.0422(8) Uani 1 1 d . . . . .
N1 N 0.49539(18) 0.7718(5) 0.11610(18) 0.0395(8) Uani 1 1 d . . . . .
C9 C 0.5635(2) 0.7927(5) 0.15259(18) 0.0293(7) Uani 1 1 d . . . . .
C8 C 0.6300(2) 0.8399(5) 0.11121(17) 0.0281(7) Uani 1 1 d . . . . .
H8 H 0.622526 0.961104 0.095244 0.034 Uiso 1 1 calc R U . . .
C21 C 0.4458(2) 0.2140(5) 0.33111(19) 0.0317(8) Uani 1 1 d . . . . .
C4 C 0.5726(2) 0.7853(5) 0.22260(19) 0.0324(8) Uani 1 1 d . . . . .
C20 C 0.3861(2) 0.1780(5) 0.38056(18) 0.0302(7) Uani 1 1 d . . . . .
H20 H 0.390577 0.054452 0.394290 0.036 Uiso 1 1 calc R U . . .
C7 C 0.7085(2) 0.8285(5) 0.15138(18) 0.0318(8) Uani 1 1 d . . . . .
H7A H 0.746622 0.888871 0.127027 0.038 Uiso 1 1 calc R U . . .
H7B H 0.723864 0.706277 0.156357 0.038 Uiso 1 1 calc R U . . .
C16 C 0.4272(2) 0.2093(5) 0.2619(2) 0.0361(8) Uani 1 1 d . . . . .
C6 C 0.7056(2) 0.9114(5) 0.22130(18) 0.0349(8) Uani 1 1 d . . . . .
H6A H 0.756553 0.908901 0.245261 0.042 Uiso 1 1 calc R U . . .
H6B H 0.689660 1.033218 0.216291 0.042 Uiso 1 1 calc R U . . .
C5 C 0.6498(2) 0.8137(6) 0.26179(19) 0.0377(9) Uani 1 1 d . . . . .
H5A H 0.671790 0.700557 0.275256 0.045 Uiso 1 1 calc R U . . .
H5B H 0.642506 0.879542 0.302624 0.045 Uiso 1 1 calc R U . . .
C10 C 0.6867(2) 0.7568(5) -0.00046(18) 0.0339(8) Uani 1 1 d . . . . .
H10 H 0.738637 0.745808 0.022512 0.041 Uiso 1 1 calc R U . . .
C2 C 0.4374(2) 0.7245(6) 0.2195(3) 0.0481(11) Uani 1 1 d . . . . .
H2 H 0.393301 0.700196 0.241018 0.058 Uiso 1 1 calc R U . . .
C3 C 0.5078(2) 0.7496(6) 0.2563(2) 0.0423(9) Uani 1 1 d . . . . .
H3 H 0.511593 0.742652 0.303332 0.051 Uiso 1 1 calc R U . . .
C15 C 0.4864(3) 0.2392(6) 0.2202(2) 0.0465(10) Uani 1 1 d . . . . .
H15 H 0.476324 0.236503 0.173396 0.056 Uiso 1 1 calc R U . . .
C19 C 0.3047(2) 0.2086(6) 0.3489(2) 0.0385(9) Uani 1 1 d . . . . .
H19A H 0.296389 0.332965 0.340348 0.046 Uiso 1 1 calc R U . . .
H19B H 0.267720 0.169223 0.379556 0.046 Uiso 1 1 calc R U . . .
C1 C 0.4347(2) 0.7364(6) 0.1499(3) 0.0479(10) Uani 1 1 d . . . . .
H1 H 0.387518 0.718640 0.125088 0.057 Uiso 1 1 calc R U . . .
C18 C 0.2938(2) 0.1063(6) 0.2828(2) 0.0445(10) Uani 1 1 d . . . . .
H18A H 0.305670 -0.016627 0.291285 0.053 Uiso 1 1 calc R U . . .
H18B H 0.240460 0.114549 0.264341 0.053 Uiso 1 1 calc R U . . .
C14 C 0.5597(3) 0.2727(6) 0.2488(3) 0.0522(12) Uani 1 1 d . . . . .
H14 H 0.599905 0.293519 0.221887 0.063 Uiso 1 1 calc R U . . .
C13 C 0.5719(2) 0.2744(6) 0.3175(3) 0.0520(12) Uani 1 1 d . . . . .
H13 H 0.621585 0.298023 0.336418 0.062 Uiso 1 1 calc R U . . .
C22 C 0.3670(3) 0.2481(6) 0.5044(2) 0.0399(9) Uani 1 1 d . . . . .
H22 H 0.311324 0.243526 0.492274 0.048 Uiso 1 1 calc R U . . .
C12 C 0.6759(3) 0.6161(6) -0.0544(2) 0.0454(10) Uani 1 1 d . . . . .
H12A H 0.684751 0.502680 -0.034017 0.068 Uiso 1 1 calc R U . . .
H12B H 0.711763 0.634909 -0.087772 0.068 Uiso 1 1 calc R U . . .
H12C H 0.624239 0.621567 -0.075611 0.068 Uiso 1 1 calc R U . . .
C11 C 0.6772(3) 0.9415(6) -0.0297(2) 0.0437(10) Uani 1 1 d . . . . .
H11A H 0.625469 0.956302 -0.049811 0.066 Uiso 1 1 calc R U . . .
H11B H 0.712736 0.958246 -0.063519 0.066 Uiso 1 1 calc R U . . .
H11C H 0.687464 1.026198 0.005829 0.066 Uiso 1 1 calc R U . . .
C17 C 0.3457(3) 0.1784(6) 0.2319(2) 0.0468(10) Uani 1 1 d . . . . .
H17A H 0.346491 0.096391 0.194541 0.056 Uiso 1 1 calc R U . . .
H17B H 0.324452 0.288347 0.214010 0.056 Uiso 1 1 calc R U . . .
C23 C 0.3842(3) 0.3956(6) 0.5550(2) 0.0503(11) Uani 1 1 d . . . . .
H23A H 0.438297 0.396239 0.569430 0.075 Uiso 1 1 calc R U . . .
H23B H 0.355283 0.377747 0.593408 0.075 Uiso 1 1 calc R U . . .
H23C H 0.370050 0.505992 0.534029 0.075 Uiso 1 1 calc R U . . .
C24 C 0.3934(3) 0.0717(6) 0.5331(2) 0.0620(14) Uani 1 1 d . . . . .
H24A H 0.383640 -0.017393 0.499113 0.093 Uiso 1 1 calc R U . . .
H24B H 0.365715 0.044371 0.571517 0.093 Uiso 1 1 calc R U . . .
H24C H 0.447617 0.076179 0.546770 0.093 Uiso 1 1 calc R U . . .
Br1A Br 0.6328(8) 0.3170(11) 0.1083(5) 0.069(4) Uani 0.063(3) 1 d . U P A 2
Br2A Br 0.3206(8) 0.6766(9) 0.3920(4) 0.050(4) Uani 0.071(3) 1 d . . P B 2


_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
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 C8 1.507(4) . ?
N2 C10 1.511(5) . ?
N4 H4A 0.8900 . ?
N4 H4B 0.8900 . ?
N4 C20 1.500(5) . ?
N4 C22 1.505(5) . ?
N3 C21 1.348(5) . ?
N3 C13 1.338(6) . ?
N1 C9 1.344(5) . ?
N1 C1 1.327(6) . ?
C9 C8 1.520(5) . ?
C9 C4 1.384(5) . ?
C8 H8 0.9800 . ?
C8 C7 1.524(5) . ?
C21 C20 1.515(5) . ?
C21 C16 1.383(6) . ?
C4 C5 1.509(5) . ?
C4 C3 1.389(5) . ?
C20 H20 0.9800 . ?
C20 C19 1.518(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C6 1.528(5) . ?
C16 C15 1.394(6) . ?
C16 C17 1.509(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C5 1.509(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C10 H10 0.9800 . ?
C10 C12 1.513(6) . ?
C10 C11 1.523(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(6) . ?
C2 C1 1.380(7) . ?
C3 H3 0.9300 . ?
C15 H15 0.9300 . ?
C15 C14 1.375(7) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C18 1.523(6) . ?
C1 H1 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C17 1.514(6) . ?
C14 H14 0.9300 . ?
C14 C13 1.360(7) . ?
C13 H13 0.9300 . ?
C22 H22 0.9800 . ?
C22 C23 1.517(6) . ?
C22 C24 1.514(6) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

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
H2A N2 H2B 107.2 . . ?
C8 N2 H2A 107.9 . . ?
C8 N2 H2B 107.9 . . ?
C8 N2 C10 117.6(3) . . ?
C10 N2 H2A 107.9 . . ?
C10 N2 H2B 107.9 . . ?
H4A N4 H4B 107.3 . . ?
C20 N4 H4A 108.1 . . ?
C20 N4 H4B 108.1 . . ?
C20 N4 C22 117.0(3) . . ?
C22 N4 H4A 108.1 . . ?
C22 N4 H4B 108.1 . . ?
C13 N3 C21 116.5(4) . . ?
C1 N1 C9 117.2(4) . . ?
N1 C9 C8 114.6(3) . . ?
N1 C9 C4 123.6(3) . . ?
C4 C9 C8 121.6(3) . . ?
N2 C8 C9 109.4(3) . . ?
N2 C8 H8 108.1 . . ?
N2 C8 C7 109.6(3) . . ?
C9 C8 H8 108.1 . . ?
C9 C8 C7 113.3(3) . . ?
C7 C8 H8 108.1 . . ?
N3 C21 C20 115.0(3) . . ?
N3 C21 C16 123.4(4) . . ?
C16 C21 C20 121.6(3) . . ?
C9 C4 C5 122.0(3) . . ?
C9 C4 C3 117.6(4) . . ?
C3 C4 C5 120.4(4) . . ?
N4 C20 C21 107.0(3) . . ?
N4 C20 H20 108.1 . . ?
N4 C20 C19 113.3(3) . . ?
C21 C20 H20 108.1 . . ?
C21 C20 C19 112.0(3) . . ?
C19 C20 H20 108.1 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C8 C7 C6 110.5(3) . . ?
H7A C7 H7B 108.1 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C21 C16 C15 117.6(4) . . ?
C21 C16 C17 121.6(3) . . ?
C15 C16 C17 120.8(4) . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C5 C6 C7 110.7(3) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C4 C5 C6 112.5(3) . . ?
C4 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
C6 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
N2 C10 H10 108.7 . . ?
N2 C10 C12 107.1(3) . . ?
N2 C10 C11 111.1(3) . . ?
C12 C10 H10 108.7 . . ?
C12 C10 C11 112.4(3) . . ?
C11 C10 H10 108.7 . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C1 C2 C3 118.0(4) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 C4 119.5(4) . . ?
C2 C3 H3 120.2 . . ?
C16 C15 H15 120.2 . . ?
C14 C15 C16 119.7(4) . . ?
C14 C15 H15 120.2 . . ?
C20 C19 H19A 110.0 . . ?
C20 C19 H19B 110.0 . . ?
C20 C19 C18 108.6(3) . . ?
H19A C19 H19B 108.4 . . ?
C18 C19 H19A 110.0 . . ?
C18 C19 H19B 110.0 . . ?
N1 C1 C2 124.0(4) . . ?
N1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
C17 C18 C19 110.6(4) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C15 C14 H14 120.9 . . ?
C13 C14 C15 118.2(4) . . ?
C13 C14 H14 120.9 . . ?
N3 C13 C14 124.7(4) . . ?
N3 C13 H13 117.7 . . ?
C14 C13 H13 117.7 . . ?
N4 C22 H22 108.8 . . ?
N4 C22 C23 108.1(3) . . ?
N4 C22 C24 110.5(3) . . ?
C23 C22 H22 108.8 . . ?
C24 C22 H22 108.8 . . ?
C24 C22 C23 111.8(4) . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C16 C17 C18 113.0(3) . . ?
C16 C17 H17A 109.0 . . ?
C16 C17 H17B 109.0 . . ?
C18 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C8 C7 C6 -166.6(3) . . . . ?
N4 C20 C19 C18 173.0(3) . . . . ?
N3 C21 C20 N4 35.0(4) . . . . ?
N3 C21 C20 C19 159.8(3) . . . . ?
N3 C21 C16 C15 -0.4(6) . . . . ?
N3 C21 C16 C17 -178.7(4) . . . . ?
N1 C9 C8 N2 -46.3(4) . . . . ?
N1 C9 C8 C7 -169.0(3) . . . . ?
N1 C9 C4 C5 -178.5(3) . . . . ?
N1 C9 C4 C3 1.8(6) . . . . ?
C9 N1 C1 C2 1.7(6) . . . . ?
C9 C8 C7 C6 -44.0(4) . . . . ?
C9 C4 C5 C6 20.7(5) . . . . ?
C9 C4 C3 C2 -0.5(6) . . . . ?
C8 N2 C10 C12 177.3(3) . . . . ?
C8 N2 C10 C11 -59.6(4) . . . . ?
C8 C9 C4 C5 -3.5(5) . . . . ?
C8 C9 C4 C3 176.9(3) . . . . ?
C8 C7 C6 C5 62.3(4) . . . . ?
C21 N3 C13 C14 -1.2(7) . . . . ?
C21 C20 C19 C18 51.8(4) . . . . ?
C21 C16 C15 C14 -0.4(6) . . . . ?
C21 C16 C17 C18 -15.5(6) . . . . ?
C4 C9 C8 N2 138.2(3) . . . . ?
C4 C9 C8 C7 15.5(5) . . . . ?
C20 N4 C22 C23 -169.4(3) . . . . ?
C20 N4 C22 C24 67.9(5) . . . . ?
C20 C21 C16 C15 -178.2(3) . . . . ?
C20 C21 C16 C17 3.5(6) . . . . ?
C20 C19 C18 C17 -65.2(4) . . . . ?
C7 C6 C5 C4 -49.4(4) . . . . ?
C16 C21 C20 N4 -147.1(3) . . . . ?
C16 C21 C20 C19 -22.3(5) . . . . ?
C16 C15 C14 C13 0.3(7) . . . . ?
C5 C4 C3 C2 179.8(4) . . . . ?
C10 N2 C8 C9 175.4(3) . . . . ?
C10 N2 C8 C7 -59.7(4) . . . . ?
C3 C4 C5 C6 -159.7(4) . . . . ?
C3 C2 C1 N1 -0.5(7) . . . . ?
C15 C16 C17 C18 166.3(4) . . . . ?
C15 C14 C13 N3 0.5(7) . . . . ?
C19 C18 C17 C16 46.0(5) . . . . ?
C1 N1 C9 C8 -177.7(3) . . . . ?
C1 N1 C9 C4 -2.3(6) . . . . ?
C1 C2 C3 C4 -0.1(6) . . . . ?
C13 N3 C21 C20 179.1(4) . . . . ?
C13 N3 C21 C16 1.2(6) . . . . ?
C22 N4 C20 C21 -166.6(3) . . . . ?
C22 N4 C20 C19 69.5(4) . . . . ?
C17 C16 C15 C14 177.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.491
_oxdiff_exptl_absorpt_empirical_full_min 0.711
####################################################################### 
# 
# 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_Mn1
_database_code_depnum_ccdc_archive 'CCDC 2248093'
loop_
_audit_author_name
_audit_author_address
'Wen-Hua Sun '
;Institute of Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2023-03-13 deposited with the CCDC.	2023-07-11 downloaded from the CCDC.
;
_audit_creation_date             2023-03-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H18 Br Mn N2 O3'
_chemical_formula_sum            'C15 H18 Br Mn N2 O3'
_chemical_formula_weight         409.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O Mn Br'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn -0.5299 2.8052 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   21.7602(3)
_cell_length_b                   12.71564(11)
_cell_length_c                   16.6797(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.0588(14)
_cell_angle_gamma                90
_cell_volume                     4306.96(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    10508
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      76.2840
_cell_measurement_theta_min      4.0770
_shelx_estimated_absorpt_T_max   0.409
_shelx_estimated_absorpt_T_min   0.220
_exptl_absorpt_coefficient_mu    7.247
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15658
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.773
_diffrn_reflns_theta_min         4.102
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     48.00 117.00   0.50    0.10    --   47.70  51.00 -15.00  138
  2  ω    123.00 169.00   0.50    0.25    --  107.36  57.00-120.00   92
  3  ω    107.00 155.00   0.50    0.25    --  107.36  51.00 -15.00   96
  4  ω     35.00 102.00   0.50    0.25    --  107.36 -77.00 120.00  134
  5  ω    -15.00  58.00   0.50    0.10    --   47.70 -51.00-161.00  146
  6  ω     35.00  61.00   0.50    0.25    --  107.36 -51.00-161.00   52
  7  ω     55.00 102.00   0.50    0.25    --  107.36 -77.00 -90.00   94
  8  ω     73.00 102.00   0.50    0.25    --  107.36 -99.00-150.00   58
  9  ω     35.00  70.00   0.50    0.25    --  107.36 -99.00-150.00   70
 10  ω    -47.00  24.00   0.50    0.10    --  -47.70  51.00 -15.00  142
 11  ω    -99.00 -58.00   0.50    0.25    -- -104.50  77.00 120.00   82
 12  ω    -62.00 -37.00   0.50    0.25    -- -104.50  57.00 150.00   50
 13  ω    -62.00 -33.00   0.50    0.25    -- -104.50  57.00 120.00   58
 14  ω    -60.00 -32.00   0.50    0.25    -- -104.50  57.00  90.00   56
 15  ω   -101.00 -33.00   0.50    0.25    -- -104.50  77.00 -30.00  136
 16  ω    -62.00 -35.00   0.50    0.25    -- -104.50  57.00 -90.00   54
 17  ω    -61.00 -33.00   0.50    0.25    -- -104.50  57.00-150.00   56
 18  ω    -62.00 -32.00   0.50    0.25    -- -104.50  57.00-180.00   60
 19  ω    -61.00 -32.00   0.50    0.25    -- -104.50  57.00-120.00   58
 20  ω   -106.00 -33.00   0.50    0.25    -- -104.50 125.00 -30.00  146
 21  ω   -169.00-104.00   0.50    0.25    -- -104.50 -57.00 -60.00  130
 22  ω   -116.00 -91.00   0.50    0.10    --  -47.70-125.00 -30.00   50
 23  ω   -119.00 -75.00   0.50    0.10    --  -47.70-125.00 -60.00   88
 24  ω   -174.00-138.00   0.50    0.25    -- -104.50 -51.00-161.00   72
 25  ω    -83.00 -36.00   0.50    0.10    --  -47.70 -51.00-161.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0245643000
_diffrn_orient_matrix_UB_12      0.0014551000
_diffrn_orient_matrix_UB_13      0.0988893000
_diffrn_orient_matrix_UB_21      -0.0558356000
_diffrn_orient_matrix_UB_22      -0.0756871000
_diffrn_orient_matrix_UB_23      -0.0021533000
_diffrn_orient_matrix_UB_31      0.0451030000
_diffrn_orient_matrix_UB_32      -0.0945987000
_diffrn_orient_matrix_UB_33      0.0032868000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4156
_reflns_number_total             4369
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.816
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       0.000073(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         4369
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0337
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0522P)²+8.6056P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.0962
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), N2(H2), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5a,H5b), C7(H7a,H7b), C6(H6a,H6b)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C2(H2a)
2.d Idealised Me refined as rotating group:
 C11(H11a,H11b,H11c), C12(H12a,H12b,H12c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.34446(2) 0.10789(2) 0.23954(2) 0.03579(10) Uani 1 1 d . . . . .
Mn1 Mn 0.33971(2) 0.28975(3) 0.29820(2) 0.02534(11) Uani 1 1 d . . . . .
N1 N 0.31212(10) 0.34106(15) 0.17396(13) 0.0275(4) Uani 1 1 d . . . . .
O1 O 0.33904(10) 0.50261(16) 0.36554(14) 0.0449(5) Uani 1 1 d . . . . .
C13 C 0.33743(12) 0.4201(2) 0.33867(16) 0.0324(5) Uani 1 1 d . . . . .
C1 C 0.35334(14) 0.3518(2) 0.13060(17) 0.0339(5) Uani 1 1 d . . . . .
H1 H 0.398961 0.338378 0.159397 0.041 Uiso 1 1 calc R U . . .
C5 C 0.14873(16) 0.4059(2) 0.00061(19) 0.0447(7) Uani 1 1 d . . . . .
H5A H 0.130829 0.347441 -0.040416 0.054 Uiso 1 1 calc R U . . .
H5B H 0.142181 0.471844 -0.032925 0.054 Uiso 1 1 calc R U . . .
C14 C 0.42738(14) 0.3011(2) 0.32202(17) 0.0375(6) Uani 1 1 d . . . . .
C10 C 0.19922(13) 0.2476(2) 0.31327(17) 0.0339(5) Uani 1 1 d . . . . .
H10 H 0.151205 0.249429 0.277499 0.041 Uiso 1 1 calc R U . . .
C7 C 0.13372(14) 0.3291(3) 0.13115(19) 0.0426(6) Uani 1 1 d . . . . .
H7A H 0.105997 0.331132 0.166957 0.051 Uiso 1 1 calc R U . . .
H7B H 0.129280 0.258496 0.104618 0.051 Uiso 1 1 calc R U . . .
C6 C 0.11010(16) 0.4125(3) 0.0609(2) 0.0479(7) Uani 1 1 d . . . . .
H6A H 0.115852 0.483182 0.087448 0.057 Uiso 1 1 calc R U . . .
H6B H 0.062635 0.402147 0.027614 0.057 Uiso 1 1 calc R U . . .
C3 C 0.26517(16) 0.3993(2) 0.00293(18) 0.0401(6) Uani 1 1 d . . . . .
H3 H 0.249229 0.418555 -0.056033 0.048 Uiso 1 1 calc R U . . .
N2 N 0.23663(10) 0.26597(16) 0.25406(13) 0.0270(4) Uani 1 1 d . . . . .
H2 H 0.230015 0.199305 0.220192 0.032 Uiso 1 1 calc R U . . .
C2 C 0.33110(16) 0.3817(2) 0.04556(18) 0.0395(6) Uani 1 1 d . . . . .
H2A H 0.361247 0.390188 0.016624 0.047 Uiso 1 1 calc R U . . .
C11 C 0.21467(15) 0.1384(2) 0.3525(2) 0.0432(6) Uani 1 1 d . . . . .
H11A H 0.205648 0.086023 0.306533 0.065 Uiso 1 1 calc R U . . .
H11B H 0.187129 0.123952 0.386514 0.065 Uiso 1 1 calc R U . . .
H11C H 0.261212 0.134761 0.389578 0.065 Uiso 1 1 calc R U . . .
O3 O 0.38034(12) 0.2022(2) 0.47360(13) 0.0530(6) Uani 1 1 d . . . . .
C12 C 0.21207(15) 0.3334(2) 0.38101(19) 0.0417(6) Uani 1 1 d . . . . .
H12A H 0.258172 0.330343 0.419836 0.063 Uiso 1 1 calc R U . . .
H12B H 0.183256 0.322808 0.413935 0.063 Uiso 1 1 calc R U . . .
H12C H 0.203057 0.402315 0.352858 0.063 Uiso 1 1 calc R U . . .
C15 C 0.36191(13) 0.2354(2) 0.40490(17) 0.0353(5) Uani 1 1 d . . . . .
C4 C 0.22163(14) 0.38852(19) 0.04680(16) 0.0343(6) Uani 1 1 d . . . . .
O2 O 0.48316(10) 0.3060(2) 0.34011(16) 0.0585(6) Uani 1 1 d . . . . .
C8 C 0.20522(12) 0.34829(19) 0.18728(15) 0.0293(5) Uani 1 1 d . . . . .
H8 H 0.207181 0.416503 0.217948 0.035 Uiso 1 1 calc R U . . .
C9 C 0.24735(12) 0.35974(18) 0.13266(15) 0.0281(5) 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 2.5275(4) . ?
Mn1 N1 2.046(2) . ?
Mn1 C13 1.797(3) . ?
Mn1 C14 1.809(3) . ?
Mn1 N2 2.116(2) . ?
Mn1 C15 1.806(3) . ?
N1 C1 1.346(3) . ?
N1 C9 1.349(3) . ?
O1 C13 1.137(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.378(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.527(4) . ?
C5 C4 1.510(4) . ?
C14 O2 1.142(4) . ?
C10 H10 1.0000 . ?
C10 N2 1.507(3) . ?
C10 C11 1.520(4) . ?
C10 C12 1.523(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C6 1.526(4) . ?
C7 C8 1.520(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C3 H3 0.9500 . ?
C3 C2 1.371(5) . ?
C3 C4 1.396(4) . ?
N2 H2 1.0000 . ?
N2 C8 1.502(3) . ?
C2 H2A 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
O3 C15 1.150(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C4 C9 1.386(3) . ?
C8 H8 1.0000 . ?
C8 C9 1.514(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Mn1 Br1 86.42(6) . . ?
N1 Mn1 N2 78.74(8) . . ?
C13 Mn1 Br1 178.75(8) . . ?
C13 Mn1 N1 92.79(10) . . ?
C13 Mn1 C14 90.76(12) . . ?
C13 Mn1 N2 95.38(10) . . ?
C13 Mn1 C15 90.96(12) . . ?
C14 Mn1 Br1 88.35(9) . . ?
C14 Mn1 N1 95.71(10) . . ?
C14 Mn1 N2 171.89(10) . . ?
N2 Mn1 Br1 85.43(6) . . ?
C15 Mn1 Br1 89.85(9) . . ?
C15 Mn1 N1 175.94(11) . . ?
C15 Mn1 C14 85.78(12) . . ?
C15 Mn1 N2 99.37(10) . . ?
C1 N1 Mn1 124.52(18) . . ?
C1 N1 C9 118.9(2) . . ?
C9 N1 Mn1 116.48(15) . . ?
O1 C13 Mn1 176.9(2) . . ?
N1 C1 H1 119.1 . . ?
N1 C1 C2 121.7(3) . . ?
C2 C1 H1 119.1 . . ?
H5A C5 H5B 107.7 . . ?
C6 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C4 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
C4 C5 C6 113.5(2) . . ?
O2 C14 Mn1 177.2(3) . . ?
N2 C10 H10 107.5 . . ?
N2 C10 C11 109.6(2) . . ?
N2 C10 C12 112.1(2) . . ?
C11 C10 H10 107.5 . . ?
C11 C10 C12 112.5(2) . . ?
C12 C10 H10 107.5 . . ?
H7A C7 H7B 108.1 . . ?
C6 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
C8 C7 H7A 109.6 . . ?
C8 C7 H7B 109.6 . . ?
C8 C7 C6 110.4(3) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C7 C6 C5 110.7(2) . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.5(2) . . ?
C4 C3 H3 120.2 . . ?
Mn1 N2 H2 103.7 . . ?
C10 N2 Mn1 123.29(16) . . ?
C10 N2 H2 103.7 . . ?
C8 N2 Mn1 107.54(14) . . ?
C8 N2 C10 112.64(18) . . ?
C8 N2 H2 103.7 . . ?
C1 C2 H2A 120.2 . . ?
C3 C2 C1 119.6(3) . . ?
C3 C2 H2A 120.2 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C15 Mn1 175.4(2) . . ?
C3 C4 C5 120.3(2) . . ?
C9 C4 C5 121.7(3) . . ?
C9 C4 C3 118.0(3) . . ?
C7 C8 H8 107.5 . . ?
N2 C8 C7 115.9(2) . . ?
N2 C8 H8 107.5 . . ?
N2 C8 C9 107.50(19) . . ?
C9 C8 C7 110.6(2) . . ?
C9 C8 H8 107.5 . . ?
N1 C9 C4 122.3(2) . . ?
N1 C9 C8 115.0(2) . . ?
C4 C9 C8 122.7(2) . . ?

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
Mn1 N1 C1 C2 176.68(19) . . . . ?
Mn1 N1 C9 C4 -175.95(18) . . . . ?
Mn1 N1 C9 C8 4.8(3) . . . . ?
Mn1 N2 C8 C7 164.91(18) . . . . ?
Mn1 N2 C8 C9 40.6(2) . . . . ?
N1 C1 C2 C3 -1.3(4) . . . . ?
C1 N1 C9 C4 0.7(3) . . . . ?
C1 N1 C9 C8 -178.5(2) . . . . ?
C5 C4 C9 N1 178.0(2) . . . . ?
C5 C4 C9 C8 -2.8(4) . . . . ?
C10 N2 C8 C7 -56.0(3) . . . . ?
C10 N2 C8 C9 179.69(19) . . . . ?
C7 C8 C9 N1 -158.3(2) . . . . ?
C7 C8 C9 C4 22.5(3) . . . . ?
C6 C5 C4 C3 -168.6(3) . . . . ?
C6 C5 C4 C9 12.7(4) . . . . ?
C6 C7 C8 N2 -174.5(2) . . . . ?
C6 C7 C8 C9 -51.8(3) . . . . ?
C3 C4 C9 N1 -0.7(4) . . . . ?
C3 C4 C9 C8 178.5(2) . . . . ?
N2 C8 C9 N1 -30.8(3) . . . . ?
N2 C8 C9 C4 149.9(2) . . . . ?
C2 C3 C4 C5 -179.1(2) . . . . ?
C2 C3 C4 C9 -0.3(4) . . . . ?
C11 C10 N2 Mn1 -71.8(3) . . . . ?
C11 C10 N2 C8 156.6(2) . . . . ?
C12 C10 N2 Mn1 53.9(3) . . . . ?
C12 C10 N2 C8 -77.8(3) . . . . ?
C4 C5 C6 C7 -42.1(4) . . . . ?
C4 C3 C2 C1 1.3(4) . . . . ?
C8 C7 C6 C5 63.4(3) . . . . ?
C9 N1 C1 C2 0.3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.702
_oxdiff_exptl_absorpt_empirical_full_min 0.781
#==END
