# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1560728'
_audit_update_record             
;
2017-07-06 deposited with the CCDC.
2017-07-31 downloaded from the CCDC.
;

_audit_creation_date             2017-03-20
_shelx_SHELXL_version_number     2014/7
_chemical_formula_moiety         'C26 H21 Br Mn N5 O3, 0.24(H2 O)'
_chemical_formula_sum            'C26 H21.48 Br Mn N5 O3.24'
_chemical_formula_weight         590.59

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

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

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

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

_cell_length_a                   10.671(4)
_cell_length_b                   11.165(4)
_cell_length_c                   11.549(5)
_cell_angle_alpha                84.587(11)
_cell_angle_beta                 65.074(11)
_cell_angle_gamma                79.68(2)
_cell_volume                     1227.4(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9992
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      30.62
_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 (Oxford Cryostream 700).
;
_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_F_000             597
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.332
_exptl_crystal_size_mid          0.296
_exptl_crystal_size_min          0.251
_exptl_absorpt_coefficient_mu    2.206
_shelx_estimated_absorpt_T_min   0.528
_shelx_estimated_absorpt_T_max   0.607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5029
_exptl_absorpt_correction_T_max  0.5881
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3.00 -2.00 -3.00 0.1270
-3.00 -2.00 0.00 0.0950
2.00 0.00 -1.00 0.1160
3.00 2.00 0.00 0.1200
-1.00 -1.00 0.00 0.0980
1.00 1.00 0.00 0.1290
3.00 0.00 -2.00 0.1200
-2.00 -3.00 0.00 0.1100
2.00 1.00 -1.00 0.1300
3.00 3.00 -1.00 0.1450
-1.00 3.00 2.00 0.1160
3.00 1.00 -2.00 0.1320
-2.00 -3.00 1.00 0.1160
3.00 2.00 -2.00 0.1440
3.00 -1.00 -3.00 0.1230
0.00 -1.00 0.00 0.1490
-1.00 3.00 1.00 0.1340
1.00 -3.00 0.00 0.1540
0.00 -2.00 1.00 0.1440
-2.00 3.00 1.00 0.1270
1.00 3.00 -3.00 0.1950
-1.00 1.00 -3.00 0.1890
1.00 -1.00 2.00 0.1240
-3.00 2.00 -1.00 0.1350
3.00 -2.00 0.00 0.1250
3.00 -2.00 3.00 0.1100
-2.00 1.00 -1.00 0.1330
1.00 0.00 3.00 0.0940
-1.00 0.00 -3.00 0.1650
-1.00 1.00 3.00 0.1030
-1.00 0.00 -1.00 0.1160
1.00 0.00 1.00 0.0700
0.00 1.00 3.00 0.0910
3.00 0.00 2.00 0.0850
2.00 1.00 3.00 0.0640
3.00 1.00 3.00 0.0620
2.00 1.00 2.00 0.0600
-3.00 2.00 0.00 0.1210

_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  'multi-layer mirror'
_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            30555
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.854
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_full        26.000
_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             4828
_reflns_number_gt                4426
_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       'APEX3 ver. 2016.1-0 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.37A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.37A (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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 the O-H bond distances of the 
water molecule were restrained to the value of 0.958, and the H-H distance to 
1.515.
The Uii displacement parameters of atom O4 of the disordered water molecule 
were restrained with ISOR keyword to approximate isotropic behavior.

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0372P)²+0.7200P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4828
_refine_ls_number_parameters     343
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0248
_refine_ls_wR_factor_ref         0.0665
_refine_ls_wR_factor_gt          0.0649
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.81586(3) 0.19081(2) 0.71274(2) 0.01576(8) Uani 1 1 d . . . . .
C1 C 0.92701(19) 0.24908(17) 0.55906(18) 0.0207(4) Uani 1 1 d . . . . .
O1 O 1.00639(14) 0.27878(14) 0.46295(14) 0.0299(3) Uani 1 1 d . . . . .
Br1 Br 0.84466(2) 0.37314(2) 0.81101(2) 0.02195(7) Uani 1 1 d . . . . .
N1 N 0.68802(16) 0.14008(14) 0.89099(14) 0.0175(3) Uani 1 1 d . . . . .
O2 O 1.07996(15) 0.06822(14) 0.72066(14) 0.0320(3) Uani 1 1 d . . . . .
C2 C 0.9763(2) 0.11352(18) 0.71971(18) 0.0218(4) Uani 1 1 d . . . . .
N2 N 0.48337(16) 0.17046(14) 1.06009(14) 0.0187(3) Uani 1 1 d . . . . .
C4 C 0.6924(2) 0.05380(17) 0.98428(17) 0.0183(4) Uani 1 1 d . . . . .
N4 N 0.76670(16) 0.43105(14) 0.43327(14) 0.0176(3) Uani 1 1 d . . . . .
N3 N 0.62203(15) 0.29685(14) 0.73717(14) 0.0163(3) Uani 1 1 d . . . . .
C3 C 0.80770(19) 0.06388(18) 0.63234(17) 0.0215(4) Uani 1 1 d . . . . .
O3 O 0.81227(16) -0.01674(13) 0.57671(14) 0.0315(3) Uani 1 1 d . . . . .
N5 N 0.66935(16) 0.26172(14) 0.46114(15) 0.0192(3) Uani 1 1 d . . . . .
C5 C 0.7978(2) -0.03996(17) 0.98566(19) 0.0219(4) Uani 1 1 d . . . . .
H5 H 0.8854 -0.0540 0.9142 0.026 Uiso 1 1 calc R U . . .
C7 C 0.6400(2) -0.09163(19) 1.20163(19) 0.0259(4) Uani 1 1 d . . . . .
H7 H 0.6243 -0.1432 1.2751 0.031 Uiso 1 1 calc R U . . .
C6 C 0.7690(2) -0.11138(18) 1.09536(19) 0.0249(4) Uani 1 1 d . . . . .
H6 H 0.8387 -0.1759 1.0990 0.030 Uiso 1 1 calc R U . . .
C9 C 0.5645(2) 0.07254(17) 1.09045(18) 0.0193(4) Uani 1 1 d . . . . .
C8 C 0.5359(2) 0.00087(18) 1.20147(18) 0.0234(4) Uani 1 1 d . . . . .
H8 H 0.4488 0.0152 1.2735 0.028 Uiso 1 1 calc R U . . .
C10 C 0.56344(19) 0.20780(16) 0.94027(17) 0.0171(4) Uani 1 1 d . . . . .
C11 C 0.52994(19) 0.30724(17) 0.86185(17) 0.0175(4) Uani 1 1 d . . . . .
C12 C 0.42258(19) 0.40513(17) 0.90570(18) 0.0205(4) Uani 1 1 d . . . . .
H12 H 0.3617 0.4110 0.9938 0.025 Uiso 1 1 calc R U . . .
C13 C 0.4056(2) 0.49359(18) 0.81970(18) 0.0218(4) Uani 1 1 d . . . . .
H13 H 0.3362 0.5635 0.8481 0.026 Uiso 1 1 calc R U . . .
C14 C 0.4916(2) 0.47871(18) 0.69118(18) 0.0211(4) Uani 1 1 d . . . . .
H14 H 0.4786 0.5362 0.6296 0.025 Uiso 1 1 calc R U . . .
C15 C 0.59690(19) 0.37898(17) 0.65329(17) 0.0177(4) Uani 1 1 d . . . . .
C16 C 0.68027(19) 0.35510(17) 0.51584(17) 0.0177(4) Uani 1 1 d . . . . .
C17 C 0.81999(19) 0.37947(16) 0.31428(17) 0.0181(4) Uani 1 1 d . . . . .
C18 C 0.9160(2) 0.41418(18) 0.19598(18) 0.0209(4) Uani 1 1 d . . . . .
H18 H 0.9608 0.4832 0.1855 0.025 Uiso 1 1 calc R U . . .
C20 C 0.8770(2) 0.24005(18) 0.11077(19) 0.0237(4) Uani 1 1 d . . . . .
H20 H 0.8968 0.1940 0.0383 0.028 Uiso 1 1 calc R U . . .
C19 C 0.9426(2) 0.34263(18) 0.09443(18) 0.0237(4) Uani 1 1 d . . . . .
H19 H 1.0069 0.3633 0.0115 0.028 Uiso 1 1 calc R U . . .
C24 C 0.7446(2) 0.65616(19) 0.4198(2) 0.0288(5) Uani 1 1 d . . . . .
H24A H 0.7738 0.6560 0.3272 0.043 Uiso 1 1 calc R U . . .
H24B H 0.7755 0.7249 0.4417 0.043 Uiso 1 1 calc R U . . .
H24C H 0.6424 0.6640 0.4630 0.043 Uiso 1 1 calc R U . . .
C21 C 0.7853(2) 0.20460(18) 0.22833(19) 0.0226(4) Uani 1 1 d . . . . .
H21 H 0.7425 0.1344 0.2387 0.027 Uiso 1 1 calc R U . . .
C25 C 0.3386(2) 0.21597(18) 1.14532(18) 0.0226(4) Uani 1 1 d . . . . .
H25A H 0.2916 0.1465 1.1926 0.027 Uiso 1 1 calc R U . . .
H25B H 0.2882 0.2564 1.0938 0.027 Uiso 1 1 calc R U . . .
C22 C 0.75687(19) 0.27569(17) 0.33290(18) 0.0192(4) Uani 1 1 d . . . . .
C26 C 0.3312(2) 0.3047(2) 1.2389(2) 0.0317(5) Uani 1 1 d . . . . .
H26A H 0.3734 0.3756 1.1925 0.048 Uiso 1 1 calc R U . . .
H26B H 0.3822 0.2653 1.2893 0.048 Uiso 1 1 calc R U . . .
H26C H 0.2332 0.3310 1.2960 0.048 Uiso 1 1 calc R U . . .
C23 C 0.8098(2) 0.53763(17) 0.46241(18) 0.0219(4) Uani 1 1 d . . . . .
H23A H 0.9129 0.5307 0.4193 0.026 Uiso 1 1 calc R U . . .
H23B H 0.7822 0.5393 0.5556 0.026 Uiso 1 1 calc R U . . .
O4 O 0.4945(17) -0.0738(13) 1.5162(17) 0.145(8) Uani 0.232(8) 1 d D U P A -1
H4A H 0.521(4) -0.1597(17) 1.525(7) 0.217 Uiso 0.232(8) 1 d D U P A -1
H4B H 0.408(2) -0.067(5) 1.507(4) 0.217 Uiso 0.232(8) 1 d D U P A -1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 C3 1.800(2) . ?
Mn1 C2 1.804(2) . ?
Mn1 C1 1.807(2) . ?
Mn1 N1 2.0272(17) . ?
Mn1 N3 2.1103(16) . ?
Mn1 Br1 2.5458(8) . ?
C1 O1 1.139(2) . ?
N1 C10 1.321(2) . ?
N1 C4 1.386(2) . ?
O2 C2 1.135(2) . ?
N2 C10 1.357(2) . ?
N2 C9 1.383(2) . ?
N2 C25 1.464(2) . ?
C4 C9 1.395(3) . ?
C4 C5 1.396(3) . ?
N4 C16 1.366(2) . ?
N4 C17 1.385(2) . ?
N4 C23 1.464(2) . ?
N3 C15 1.347(2) . ?
N3 C11 1.360(2) . ?
C3 O3 1.137(2) . ?
N5 C16 1.315(2) . ?
N5 C22 1.390(2) . ?
C5 C6 1.380(3) . ?
C5 H5 0.9500 . ?
C7 C8 1.375(3) . ?
C7 C6 1.403(3) . ?
C7 H7 0.9500 . ?
C6 H6 0.9500 . ?
C9 C8 1.393(3) . ?
C8 H8 0.9500 . ?
C10 C11 1.457(3) . ?
C11 C12 1.389(3) . ?
C12 C13 1.377(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.479(3) . ?
C17 C18 1.389(3) . ?
C17 C22 1.397(3) . ?
C18 C19 1.382(3) . ?
C18 H18 0.9500 . ?
C20 C21 1.369(3) . ?
C20 C19 1.405(3) . ?
C20 H20 0.9500 . ?
C19 H19 0.9500 . ?
C24 C23 1.521(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C21 C22 1.402(3) . ?
C21 H21 0.9500 . ?
C25 C26 1.502(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
O4 H4A 0.9584(11) . ?
O4 H4B 0.9584(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 Mn1 C2 90.53(9) . . ?
C3 Mn1 C1 88.36(9) . . ?
C2 Mn1 C1 85.58(9) . . ?
C3 Mn1 N1 96.33(8) . . ?
C2 Mn1 N1 95.91(8) . . ?
C1 Mn1 N1 175.05(8) . . ?
C3 Mn1 N3 99.02(8) . . ?
C2 Mn1 N3 169.00(7) . . ?
C1 Mn1 N3 100.06(7) . . ?
N1 Mn1 N3 77.71(6) . . ?
C3 Mn1 Br1 175.49(6) . . ?
C2 Mn1 Br1 87.63(7) . . ?
C1 Mn1 Br1 87.39(7) . . ?
N1 Mn1 Br1 87.95(5) . . ?
N3 Mn1 Br1 83.23(5) . . ?
O1 C1 Mn1 174.06(16) . . ?
C10 N1 C4 106.13(15) . . ?
C10 N1 Mn1 115.25(12) . . ?
C4 N1 Mn1 138.57(13) . . ?
O2 C2 Mn1 177.26(18) . . ?
C10 N2 C9 106.29(15) . . ?
C10 N2 C25 130.11(16) . . ?
C9 N2 C25 123.57(16) . . ?
N1 C4 C9 108.30(16) . . ?
N1 C4 C5 131.33(17) . . ?
C9 C4 C5 120.37(17) . . ?
C16 N4 C17 105.87(15) . . ?
C16 N4 C23 128.50(16) . . ?
C17 N4 C23 125.29(15) . . ?
C15 N3 C11 117.27(15) . . ?
C15 N3 Mn1 126.71(12) . . ?
C11 N3 Mn1 112.89(12) . . ?
O3 C3 Mn1 175.25(17) . . ?
C16 N5 C22 104.15(16) . . ?
C6 C5 C4 117.14(18) . . ?
C6 C5 H5 121.4 . . ?
C4 C5 H5 121.4 . . ?
C8 C7 C6 121.30(18) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C5 C6 C7 122.00(19) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
N2 C9 C8 130.86(18) . . ?
N2 C9 C4 106.71(16) . . ?
C8 C9 C4 122.43(18) . . ?
C7 C8 C9 116.75(18) . . ?
C7 C8 H8 121.6 . . ?
C9 C8 H8 121.6 . . ?
N1 C10 N2 112.56(16) . . ?
N1 C10 C11 117.98(16) . . ?
N2 C10 C11 129.45(16) . . ?
N3 C11 C12 122.47(17) . . ?
N3 C11 C10 111.55(15) . . ?
C12 C11 C10 125.92(16) . . ?
C13 C12 C11 119.12(17) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 118.80(18) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
C13 C14 C15 119.30(17) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
N3 C15 C14 122.58(17) . . ?
N3 C15 C16 117.41(16) . . ?
C14 C15 C16 119.89(16) . . ?
N5 C16 N4 114.14(16) . . ?
N5 C16 C15 121.97(17) . . ?
N4 C16 C15 123.74(17) . . ?
N4 C17 C18 131.48(18) . . ?
N4 C17 C22 105.60(16) . . ?
C18 C17 C22 122.91(17) . . ?
C19 C18 C17 116.18(18) . . ?
C19 C18 H18 121.9 . . ?
C17 C18 H18 121.9 . . ?
C21 C20 C19 121.78(18) . . ?
C21 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C18 C19 C20 121.64(19) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C20 C21 C22 117.60(18) . . ?
C20 C21 H21 121.2 . . ?
C22 C21 H21 121.2 . . ?
N2 C25 C26 111.77(17) . . ?
N2 C25 H25A 109.3 . . ?
C26 C25 H25A 109.3 . . ?
N2 C25 H25B 109.3 . . ?
C26 C25 H25B 109.3 . . ?
H25A C25 H25B 107.9 . . ?
N5 C22 C17 110.20(16) . . ?
N5 C22 C21 129.97(18) . . ?
C17 C22 C21 119.83(18) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N4 C23 C24 112.22(16) . . ?
N4 C23 H23A 109.2 . . ?
C24 C23 H23A 109.2 . . ?
N4 C23 H23B 109.2 . . ?
C24 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
H4A O4 H4B 104.44(16) . . ?

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
C10 N1 C4 C9 0.6(2) . . . . ?
Mn1 N1 C4 C9 177.98(14) . . . . ?
C10 N1 C4 C5 -179.3(2) . . . . ?
Mn1 N1 C4 C5 -2.0(3) . . . . ?
N1 C4 C5 C6 179.90(19) . . . . ?
C9 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 C7 0.0(3) . . . . ?
C8 C7 C6 C5 -0.3(3) . . . . ?
C10 N2 C9 C8 178.8(2) . . . . ?
C25 N2 C9 C8 -3.0(3) . . . . ?
C10 N2 C9 C4 -0.75(19) . . . . ?
C25 N2 C9 C4 177.51(17) . . . . ?
N1 C4 C9 N2 0.1(2) . . . . ?
C5 C4 C9 N2 -179.96(16) . . . . ?
N1 C4 C9 C8 -179.48(17) . . . . ?
C5 C4 C9 C8 0.5(3) . . . . ?
C6 C7 C8 C9 0.7(3) . . . . ?
N2 C9 C8 C7 179.74(19) . . . . ?
C4 C9 C8 C7 -0.8(3) . . . . ?
C4 N1 C10 N2 -1.2(2) . . . . ?
Mn1 N1 C10 N2 -179.22(12) . . . . ?
C4 N1 C10 C11 179.89(16) . . . . ?
Mn1 N1 C10 C11 1.8(2) . . . . ?
C9 N2 C10 N1 1.2(2) . . . . ?
C25 N2 C10 N1 -176.88(17) . . . . ?
C9 N2 C10 C11 -179.98(18) . . . . ?
C25 N2 C10 C11 1.9(3) . . . . ?
C15 N3 C11 C12 -7.0(3) . . . . ?
Mn1 N3 C11 C12 154.35(15) . . . . ?
C15 N3 C11 C10 175.71(15) . . . . ?
Mn1 N3 C11 C10 -22.92(18) . . . . ?
N1 C10 C11 N3 14.5(2) . . . . ?
N2 C10 C11 N3 -164.20(18) . . . . ?
N1 C10 C11 C12 -162.62(18) . . . . ?
N2 C10 C11 C12 18.6(3) . . . . ?
N3 C11 C12 C13 1.9(3) . . . . ?
C10 C11 C12 C13 178.76(18) . . . . ?
C11 C12 C13 C14 3.4(3) . . . . ?
C12 C13 C14 C15 -3.5(3) . . . . ?
C11 N3 C15 C14 7.0(3) . . . . ?
Mn1 N3 C15 C14 -151.46(15) . . . . ?
C11 N3 C15 C16 -168.86(16) . . . . ?
Mn1 N3 C15 C16 32.7(2) . . . . ?
C13 C14 C15 N3 -1.9(3) . . . . ?
C13 C14 C15 C16 173.88(18) . . . . ?
C22 N5 C16 N4 1.0(2) . . . . ?
C22 N5 C16 C15 176.60(16) . . . . ?
C17 N4 C16 N5 -2.0(2) . . . . ?
C23 N4 C16 N5 -175.42(16) . . . . ?
C17 N4 C16 C15 -177.48(16) . . . . ?
C23 N4 C16 C15 9.1(3) . . . . ?
N3 C15 C16 N5 65.5(2) . . . . ?
C14 C15 C16 N5 -110.5(2) . . . . ?
N3 C15 C16 N4 -119.35(19) . . . . ?
C14 C15 C16 N4 64.7(3) . . . . ?
C16 N4 C17 C18 -177.53(19) . . . . ?
C23 N4 C17 C18 -3.8(3) . . . . ?
C16 N4 C17 C22 2.01(19) . . . . ?
C23 N4 C17 C22 175.74(16) . . . . ?
N4 C17 C18 C19 -177.95(18) . . . . ?
C22 C17 C18 C19 2.6(3) . . . . ?
C17 C18 C19 C20 -0.6(3) . . . . ?
C21 C20 C19 C18 -1.1(3) . . . . ?
C19 C20 C21 C22 1.0(3) . . . . ?
C10 N2 C25 C26 -96.7(2) . . . . ?
C9 N2 C25 C26 85.5(2) . . . . ?
C16 N5 C22 C17 0.4(2) . . . . ?
C16 N5 C22 C21 -178.65(19) . . . . ?
N4 C17 C22 N5 -1.5(2) . . . . ?
C18 C17 C22 N5 178.07(16) . . . . ?
N4 C17 C22 C21 177.61(16) . . . . ?
C18 C17 C22 C21 -2.8(3) . . . . ?
C20 C21 C22 N5 179.87(18) . . . . ?
C20 C21 C22 C17 0.9(3) . . . . ?
C16 N4 C23 C24 -109.5(2) . . . . ?
C17 N4 C23 C24 78.2(2) . . . . ?

_refine_diff_density_max         0.486
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.062



_chemical_properties_physical    ', 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_1
_database_code_depnum_ccdc_archive 'CCDC 1560724'
_audit_update_record             
;
2017-07-06 deposited with the CCDC.
2017-07-31 downloaded from the CCDC.
;

_audit_creation_date             2016-12-19
_shelx_SHELXL_version_number     2014/7
_chemical_formula_moiety         'C22 H13 Br Mn N5 O3, C3 H6 O'
_chemical_formula_sum            'C25 H19 Br Mn N5 O4'
_chemical_formula_weight         588.30

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

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

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

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

_cell_length_a                   28.855(11)
_cell_length_b                   6.950(3)
_cell_length_c                   25.152(9)
_cell_angle_alpha                90
_cell_angle_beta                 106.66(3)
_cell_angle_gamma                90
_cell_volume                     4832(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9265
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      28.00
_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       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_F_000             2368
_exptl_crystal_recrystallization_method 
'recrystallised from acetone by evaporation'
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.659
_exptl_crystal_size_mid          0.244
_exptl_crystal_size_min          0.074
_exptl_absorpt_coefficient_mu    2.243
_shelx_estimated_absorpt_T_min   0.320
_shelx_estimated_absorpt_T_max   0.852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5700
_exptl_absorpt_correction_T_max  0.7457
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 1.00 0.2590
-1.00 0.00 0.00 0.1060
-1.00 2.00 0.00 0.2610
-3.00 0.00 -1.00 0.0970
-2.00 -3.00 0.00 0.3240
0.00 0.00 1.00 0.0280
0.00 0.00 -1.00 0.0370
3.00 0.00 1.00 0.0790
-1.00 -1.00 1.00 0.3040
1.00 -1.00 3.00 0.2150
2.00 -1.00 2.00 0.2350

_exptl_absorpt_process_details   'SadAbs 2014/5 (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            29317
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.947
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4772
_reflns_number_gt                4150
_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. V8.34A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.34A (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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 anisotropic displacement parameters
of atom C3, which is part of a terminally bound carbonyl group, were 
affected by bonding electron density deformation showing the ?sliding effect?
(D. Braga and T.F. Koetzle,  Acta Cryst., 1988, B44, 151-155). Hence, the 
atomic displacement parameters of atom C3 were restrained using DELU keyword
in ShelXL input ('rigid bond' restraint for the bonds in the connectivity 
list). In addition, the Uii displacement parameters of atom C3 were 
restrained with ISOR keyword to approximate isotropic behavior.

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0414P)²+14.2008P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_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         4772
_refine_ls_number_parameters     328
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0866
_refine_ls_wR_factor_gt          0.0825
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.61174(2) 0.75571(5) 0.40393(2) 0.01332(11) Uani 1 1 d . . . . .
C1 C 0.65346(10) 0.7877(4) 0.36294(11) 0.0176(6) Uani 1 1 d . . . . .
O1 O 0.67774(7) 0.8281(3) 0.33537(8) 0.0247(5) Uani 1 1 d . . . . .
Br1 Br 0.57718(2) 0.43782(4) 0.36111(2) 0.01926(9) Uani 1 1 d . . . . .
N1 N 0.56759(8) 0.7265(3) 0.45328(9) 0.0139(4) Uani 1 1 d . . . . .
C2 C 0.56799(10) 0.8734(4) 0.34734(12) 0.0197(6) Uani 1 1 d . . . . .
O2 O 0.54165(8) 0.9449(3) 0.31004(8) 0.0278(5) Uani 1 1 d . . . . .
N2 N 0.55993(8) 0.6802(3) 0.53763(9) 0.0157(5) Uani 1 1 d . . . . .
H2A H 0.5679 0.6534 0.5733 0.019 Uiso 1 1 calc R U . . .
C3 C 0.63493(9) 0.9877(4) 0.43678(10) 0.0102(5) Uani 1 1 d . U . . .
O3 O 0.64870(7) 1.1225(3) 0.45501(8) 0.0224(4) Uani 1 1 d . . . . .
N3 N 0.65699(8) 0.6069(3) 0.47365(9) 0.0130(4) Uani 1 1 d . . . . .
O4 O 0.59561(9) 0.6115(5) 0.65204(9) 0.0499(7) Uani 1 1 d . . . . .
C4 C 0.52005(9) 0.7638(4) 0.45155(11) 0.0160(5) Uani 1 1 d . . . . .
N4 N 0.76601(8) 0.5510(3) 0.43484(10) 0.0183(5) Uani 1 1 d . . . . .
C5 C 0.48042(10) 0.8160(4) 0.40758(12) 0.0204(6) Uani 1 1 d . . . . .
H5 H 0.4834 0.8358 0.3714 0.024 Uiso 1 1 calc R U . . .
N5 N 0.69571(8) 0.4173(3) 0.38654(9) 0.0169(5) Uani 1 1 d . . . . .
H5N H 0.6658 0.3745 0.3790 0.020 Uiso 1 1 calc R U . . .
C7 C 0.43183(11) 0.8101(4) 0.47205(13) 0.0250(7) Uani 1 1 d . . . . .
H7 H 0.4010 0.8267 0.4779 0.030 Uiso 1 1 calc R U . . .
C6 C 0.43659(10) 0.8378(4) 0.41863(13) 0.0250(6) Uani 1 1 d . . . . .
H6 H 0.4089 0.8725 0.3893 0.030 Uiso 1 1 calc R U . . .
C9 C 0.51498(10) 0.7351(4) 0.50494(12) 0.0168(6) Uani 1 1 d . . . . .
C8 C 0.47056(11) 0.7596(4) 0.51616(13) 0.0215(6) Uani 1 1 d . . . . .
H8 H 0.4673 0.7422 0.5524 0.026 Uiso 1 1 calc R U . . .
C23 C 0.58004(12) 0.5926(5) 0.69146(12) 0.0322(7) Uani 1 1 d . . . . .
C22 C 0.72554(10) 0.4067(4) 0.35271(12) 0.0184(6) Uani 1 1 d . . . . .
C21 C 0.71928(11) 0.3299(4) 0.29982(12) 0.0243(6) Uani 1 1 d . . . . .
H21 H 0.6896 0.2727 0.2795 0.029 Uiso 1 1 calc R U . . .
C20 C 0.75802(12) 0.3412(4) 0.27860(13) 0.0288(7) Uani 1 1 d . . . . .
H20 H 0.7551 0.2899 0.2428 0.035 Uiso 1 1 calc R U . . .
C24 C 0.5864(2) 0.4104(6) 0.72321(17) 0.0711(16) Uani 1 1 d . . . . .
H24A H 0.5547 0.3622 0.7241 0.107 Uiso 1 1 calc R U . . .
H24B H 0.6067 0.4334 0.7612 0.107 Uiso 1 1 calc R U . . .
H24C H 0.6020 0.3150 0.7053 0.107 Uiso 1 1 calc R U . . .
C25 C 0.55413(16) 0.7491(6) 0.70974(18) 0.0533(11) Uani 1 1 d . . . . .
H25A H 0.5692 0.7744 0.7493 0.080 Uiso 1 1 calc R U . . .
H25B H 0.5203 0.7121 0.7038 0.080 Uiso 1 1 calc R U . . .
H25C H 0.5556 0.8656 0.6883 0.080 Uiso 1 1 calc R U . . .
C19 C 0.80176(12) 0.4264(4) 0.30848(14) 0.0287(7) Uani 1 1 d . . . . .
H19 H 0.8277 0.4318 0.2923 0.034 Uiso 1 1 calc R U . . .
C18 C 0.80810(11) 0.5023(4) 0.36055(13) 0.0249(6) Uani 1 1 d . . . . .
H18 H 0.8378 0.5603 0.3804 0.030 Uiso 1 1 calc R U . . .
C17 C 0.76915(10) 0.4911(4) 0.38338(12) 0.0188(6) Uani 1 1 d . . . . .
C16 C 0.72144(10) 0.5070(4) 0.43419(11) 0.0159(5) Uani 1 1 d . . . . .
C15 C 0.70204(9) 0.5352(3) 0.48174(11) 0.0151(5) Uani 1 1 d . . . . .
C14 C 0.73065(10) 0.4773(4) 0.53395(11) 0.0182(6) Uani 1 1 d . . . . .
H14 H 0.7626 0.4322 0.5385 0.022 Uiso 1 1 calc R U . . .
C13 C 0.71240(10) 0.4858(4) 0.57881(11) 0.0200(6) Uani 1 1 d . . . . .
H13 H 0.7318 0.4495 0.6147 0.024 Uiso 1 1 calc R U . . .
C12 C 0.66547(10) 0.5480(4) 0.57078(11) 0.0176(6) Uani 1 1 d . . . . .
H12 H 0.6514 0.5489 0.6006 0.021 Uiso 1 1 calc R U . . .
C11 C 0.63942(9) 0.6089(4) 0.51838(11) 0.0144(5) Uani 1 1 d . . . . .
C10 C 0.58964(9) 0.6750(4) 0.50472(10) 0.0140(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
Mn1 C2 1.805(3) . ?
Mn1 C1 1.809(3) . ?
Mn1 C3 1.847(3) . ?
Mn1 N1 2.028(2) . ?
Mn1 N3 2.130(2) . ?
Mn1 Br1 2.5336(10) . ?
C1 O1 1.153(3) . ?
N1 C10 1.317(3) . ?
N1 C4 1.384(3) . ?
C2 O2 1.138(3) . ?
N2 C10 1.352(3) . ?
N2 C9 1.376(4) . ?
N2 H2A 0.8800 . ?
C3 O3 1.068(3) . ?
N3 C15 1.352(3) . ?
N3 C11 1.360(3) . ?
O4 C23 1.208(4) . ?
C4 C5 1.392(4) . ?
C4 C9 1.406(4) . ?
N4 C16 1.317(4) . ?
N4 C17 1.387(4) . ?
C5 C6 1.379(4) . ?
C5 H5 0.9500 . ?
N5 C16 1.366(3) . ?
N5 C22 1.375(4) . ?
N5 H5N 0.8800 . ?
C7 C8 1.375(4) . ?
C7 C6 1.403(4) . ?
C7 H7 0.9500 . ?
C6 H6 0.9500 . ?
C9 C8 1.400(4) . ?
C8 H8 0.9500 . ?
C23 C25 1.467(5) . ?
C23 C24 1.480(5) . ?
C22 C21 1.396(4) . ?
C22 C17 1.402(4) . ?
C21 C20 1.372(4) . ?
C21 H21 0.9500 . ?
C20 C19 1.402(5) . ?
C20 H20 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C19 C18 1.375(4) . ?
C19 H19 0.9500 . ?
C18 C17 1.403(4) . ?
C18 H18 0.9500 . ?
C16 C15 1.472(4) . ?
C15 C14 1.395(4) . ?
C14 C13 1.376(4) . ?
C14 H14 0.9500 . ?
C13 C12 1.380(4) . ?
C13 H13 0.9500 . ?
C12 C11 1.383(4) . ?
C12 H12 0.9500 . ?
C11 C10 1.452(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 Mn1 C1 85.66(12) . . ?
C2 Mn1 C3 92.23(12) . . ?
C1 Mn1 C3 86.15(11) . . ?
C2 Mn1 N1 96.20(11) . . ?
C1 Mn1 N1 176.98(11) . . ?
C3 Mn1 N1 91.39(10) . . ?
C2 Mn1 N3 173.87(11) . . ?
C1 Mn1 N3 100.24(11) . . ?
C3 Mn1 N3 89.86(10) . . ?
N1 Mn1 N3 77.98(9) . . ?
C2 Mn1 Br1 87.65(10) . . ?
C1 Mn1 Br1 96.32(9) . . ?
C3 Mn1 Br1 177.51(8) . . ?
N1 Mn1 Br1 86.16(6) . . ?
N3 Mn1 Br1 90.01(7) . . ?
O1 C1 Mn1 172.3(2) . . ?
C10 N1 C4 106.1(2) . . ?
C10 N1 Mn1 114.64(17) . . ?
C4 N1 Mn1 138.83(18) . . ?
O2 C2 Mn1 176.8(3) . . ?
C10 N2 C9 107.2(2) . . ?
C10 N2 H2A 126.4 . . ?
C9 N2 H2A 126.4 . . ?
O3 C3 Mn1 178.7(2) . . ?
C15 N3 C11 116.7(2) . . ?
C15 N3 Mn1 129.71(18) . . ?
C11 N3 Mn1 112.97(17) . . ?
N1 C4 C5 130.9(3) . . ?
N1 C4 C9 108.5(2) . . ?
C5 C4 C9 120.6(2) . . ?
C16 N4 C17 104.1(2) . . ?
C6 C5 C4 117.4(3) . . ?
C6 C5 H5 121.3 . . ?
C4 C5 H5 121.3 . . ?
C16 N5 C22 106.7(2) . . ?
C16 N5 H5N 126.6 . . ?
C22 N5 H5N 126.6 . . ?
C8 C7 C6 121.9(3) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C5 C6 C7 121.7(3) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
N2 C9 C8 132.4(3) . . ?
N2 C9 C4 105.8(2) . . ?
C8 C9 C4 121.8(3) . . ?
C7 C8 C9 116.6(3) . . ?
C7 C8 H8 121.7 . . ?
C9 C8 H8 121.7 . . ?
O4 C23 C25 121.3(3) . . ?
O4 C23 C24 121.2(4) . . ?
C25 C23 C24 117.4(3) . . ?
N5 C22 C21 132.6(3) . . ?
N5 C22 C17 105.0(2) . . ?
C21 C22 C17 122.3(3) . . ?
C20 C21 C22 116.9(3) . . ?
C20 C21 H21 121.6 . . ?
C22 C21 H21 121.6 . . ?
C21 C20 C19 121.6(3) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C18 C19 C20 121.8(3) . . ?
C18 C19 H19 119.1 . . ?
C20 C19 H19 119.1 . . ?
C19 C18 C17 117.7(3) . . ?
C19 C18 H18 121.1 . . ?
C17 C18 H18 121.1 . . ?
N4 C17 C22 110.5(2) . . ?
N4 C17 C18 129.7(3) . . ?
C22 C17 C18 119.7(3) . . ?
N4 C16 N5 113.6(2) . . ?
N4 C16 C15 123.8(2) . . ?
N5 C16 C15 122.4(2) . . ?
N3 C15 C14 122.1(2) . . ?
N3 C15 C16 120.0(2) . . ?
C14 C15 C16 117.8(2) . . ?
C13 C14 C15 119.8(3) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C13 C12 118.9(3) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C12 C11 118.5(3) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
N3 C11 C12 123.7(2) . . ?
N3 C11 C10 112.7(2) . . ?
C12 C11 C10 123.6(2) . . ?
N1 C10 N2 112.4(2) . . ?
N1 C10 C11 119.0(2) . . ?
N2 C10 C11 128.4(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
C10 N1 C4 C5 -177.3(3) . . . . ?
Mn1 N1 C4 C5 11.2(5) . . . . ?
C10 N1 C4 C9 1.0(3) . . . . ?
Mn1 N1 C4 C9 -170.57(19) . . . . ?
N1 C4 C5 C6 178.0(3) . . . . ?
C9 C4 C5 C6 0.0(4) . . . . ?
C4 C5 C6 C7 0.4(4) . . . . ?
C8 C7 C6 C5 -0.1(4) . . . . ?
C10 N2 C9 C8 178.2(3) . . . . ?
C10 N2 C9 C4 -0.6(3) . . . . ?
N1 C4 C9 N2 -0.2(3) . . . . ?
C5 C4 C9 N2 178.3(2) . . . . ?
N1 C4 C9 C8 -179.2(2) . . . . ?
C5 C4 C9 C8 -0.7(4) . . . . ?
C6 C7 C8 C9 -0.7(4) . . . . ?
N2 C9 C8 C7 -177.6(3) . . . . ?
C4 C9 C8 C7 1.1(4) . . . . ?
C16 N5 C22 C21 179.4(3) . . . . ?
C16 N5 C22 C17 0.8(3) . . . . ?
N5 C22 C21 C20 -178.6(3) . . . . ?
C17 C22 C21 C20 -0.3(4) . . . . ?
C22 C21 C20 C19 -0.3(4) . . . . ?
C21 C20 C19 C18 0.2(5) . . . . ?
C20 C19 C18 C17 0.3(4) . . . . ?
C16 N4 C17 C22 -1.2(3) . . . . ?
C16 N4 C17 C18 179.6(3) . . . . ?
N5 C22 C17 N4 0.2(3) . . . . ?
C21 C22 C17 N4 -178.5(2) . . . . ?
N5 C22 C17 C18 179.5(2) . . . . ?
C21 C22 C17 C18 0.8(4) . . . . ?
C19 C18 C17 N4 178.3(3) . . . . ?
C19 C18 C17 C22 -0.8(4) . . . . ?
C17 N4 C16 N5 1.8(3) . . . . ?
C17 N4 C16 C15 176.7(2) . . . . ?
C22 N5 C16 N4 -1.8(3) . . . . ?
C22 N5 C16 C15 -176.7(2) . . . . ?
C11 N3 C15 C14 -4.1(4) . . . . ?
Mn1 N3 C15 C14 166.25(19) . . . . ?
C11 N3 C15 C16 172.9(2) . . . . ?
Mn1 N3 C15 C16 -16.8(3) . . . . ?
N4 C16 C15 N3 137.6(3) . . . . ?
N5 C16 C15 N3 -48.0(3) . . . . ?
N4 C16 C15 C14 -45.4(4) . . . . ?
N5 C16 C15 C14 129.1(3) . . . . ?
N3 C15 C14 C13 2.5(4) . . . . ?
C16 C15 C14 C13 -174.5(2) . . . . ?
C15 C14 C13 C12 1.4(4) . . . . ?
C14 C13 C12 C11 -3.3(4) . . . . ?
C15 N3 C11 C12 2.0(4) . . . . ?
Mn1 N3 C11 C12 -169.9(2) . . . . ?
C15 N3 C11 C10 -175.7(2) . . . . ?
Mn1 N3 C11 C10 12.3(3) . . . . ?
C13 C12 C11 N3 1.7(4) . . . . ?
C13 C12 C11 C10 179.2(2) . . . . ?
C4 N1 C10 N2 -1.5(3) . . . . ?
Mn1 N1 C10 N2 172.44(16) . . . . ?
C4 N1 C10 C11 174.3(2) . . . . ?
Mn1 N1 C10 C11 -11.8(3) . . . . ?
C9 N2 C10 N1 1.3(3) . . . . ?
C9 N2 C10 C11 -173.9(2) . . . . ?
N3 C11 C10 N1 -0.9(3) . . . . ?
C12 C11 C10 N1 -178.6(2) . . . . ?
N3 C11 C10 N2 174.1(2) . . . . ?
C12 C11 C10 N2 -3.7(4) . . . . ?

_refine_diff_density_max         0.929
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.084



_chemical_properties_physical    ', Light-sensitive'
