# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_C13H19N5O3BrMn
_database_code_depnum_ccdc_archive 'CCDC 2248412'
loop_
_audit_author_name
_audit_author_address
'Yoshihito Kayaki'
;Tokyo Institute of Technology
Japan
;
_audit_update_record             
;
2023-09-20 deposited with the CCDC.	2023-09-21 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C13 H19 Br Mn N5 O3'
_chemical_formula_moiety         'C13 H19 Mn N5 O3, Br'
_chemical_formula_weight         428.17
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   10.695(2)
_cell_length_b                   16.189(3)
_cell_length_c                   9.9943(17)
_cell_angle_alpha                90.0000
_cell_angle_beta                 93.985(3)
_cell_angle_gamma                90.0000
_cell_volume                     1726.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5145
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      27.49
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864.00
_exptl_absorpt_coefficient_mu    3.106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.615
_exptl_absorpt_correction_T_max  0.940

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            14053
_diffrn_reflns_av_unetI/netI     0.0807
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         3.154
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3926
_reflns_number_gt                2825
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.0949
_refine_ls_wR_factor_gt          0.0927
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3926
_refine_ls_number_parameters     210
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0426P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         1.33
_refine_diff_density_min         -0.52
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Mn Mn 0.3368 0.7283
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.68128(3) 0.07804(2) 0.19634(3) 0.01788(11) Uani 1 1 d . . . . .
Mn1 Mn 0.28977(4) 0.12175(3) 0.33365(5) 0.01143(13) Uani 1 1 d . . . . .
O1 O 0.1343(2) 0.19115(15) 0.5385(2) 0.0234(6) Uani 1 1 d . . . . .
O2 O 0.3749(2) 0.29043(15) 0.2713(2) 0.0242(6) Uani 1 1 d . . . . .
O3 O 0.5056(2) 0.10707(16) 0.5354(2) 0.0253(6) Uani 1 1 d . . . . .
N1 N 0.3758(2) 0.06655(15) 0.1716(3) 0.0113(6) Uani 1 1 d . . . . .
H1 H 0.4657 0.0839 0.1767 0.014 Uiso 1 1 calc R U . . .
N2 N 0.2428(2) 0.00243(17) 0.3610(3) 0.0135(6) Uani 1 1 d . . . . .
N3 N 0.2402(2) -0.12963(16) 0.2919(3) 0.0166(6) Uani 1 1 d . . . . .
N4 N 0.1481(2) 0.12369(16) 0.1871(3) 0.0118(6) Uani 1 1 d . . . . .
N5 N 0.0828(2) 0.10516(18) -0.0281(3) 0.0172(6) Uani 1 1 d . . . . .
C1 C 0.3716(3) -0.02529(19) 0.1779(3) 0.0136(7) Uani 1 1 d . . . . .
H2 H 0.4562 -0.0471 0.2039 0.016 Uiso 1 1 calc R U . . .
H3 H 0.3442 -0.0478 0.0885 0.016 Uiso 1 1 calc R U . . .
C2 C 0.2822(3) -0.0516(2) 0.2782(3) 0.0135(7) Uani 1 1 d . . . . .
C3 C 0.1630(3) -0.0419(2) 0.4528(3) 0.0187(7) Uani 1 1 d . . . . .
H4 H 0.0736 -0.0276 0.4338 0.022 Uiso 1 1 calc R U . . .
H5 H 0.1880 -0.0286 0.5476 0.022 Uiso 1 1 calc R U . . .
C4 C 0.1865(3) -0.1334(2) 0.4230(4) 0.0208(8) Uani 1 1 d . . . . .
H6 H 0.2461 -0.1582 0.4918 0.025 Uiso 1 1 calc R U . . .
H7 H 0.1074 -0.1653 0.4182 0.025 Uiso 1 1 calc R U . . .
C5 C 0.2991(3) -0.2022(2) 0.2374(4) 0.0252(8) Uani 1 1 d . . . . .
H8 H 0.2392 -0.2481 0.2320 0.038 Uiso 1 1 calc R U . . .
H9 H 0.3727 -0.2176 0.2959 0.038 Uiso 1 1 calc R U . . .
H10 H 0.3251 -0.1896 0.1475 0.038 Uiso 1 1 calc R U . . .
C6 C 0.3144(3) 0.0991(2) 0.0444(3) 0.0129(7) Uani 1 1 d . . . . .
H11 H 0.3248 0.0597 -0.0299 0.016 Uiso 1 1 calc R U . . .
H12 H 0.3520 0.1526 0.0212 0.016 Uiso 1 1 calc R U . . .
C7 C 0.1784(3) 0.10988(19) 0.0667(3) 0.0118(7) Uani 1 1 d . . . . .
C8 C 0.0106(3) 0.1313(2) 0.1838(3) 0.0179(7) Uani 1 1 d . . . . .
H13 H -0.0140 0.1839 0.2254 0.022 Uiso 1 1 calc R U . . .
H14 H -0.0263 0.0848 0.2319 0.022 Uiso 1 1 calc R U . . .
C9 C -0.0326(3) 0.1295(2) 0.0335(3) 0.0183(7) Uani 1 1 d . . . . .
H15 H -0.1002 0.0885 0.0147 0.022 Uiso 1 1 calc R U . . .
H16 H -0.0622 0.1845 0.0016 0.022 Uiso 1 1 calc R U . . .
C10 C 0.0916(3) 0.1115(2) -0.1714(3) 0.0206(8) Uani 1 1 d . . . . .
H17 H 0.1713 0.0877 -0.1955 0.031 Uiso 1 1 calc R U . . .
H18 H 0.0877 0.1697 -0.1981 0.031 Uiso 1 1 calc R U . . .
H19 H 0.0219 0.0814 -0.2178 0.031 Uiso 1 1 calc R U . . .
C11 C 0.1950(3) 0.1631(2) 0.4600(3) 0.0153(7) Uani 1 1 d . . . . .
C12 C 0.3408(3) 0.2248(2) 0.2935(3) 0.0159(7) Uani 1 1 d . . . . .
C13 C 0.4234(3) 0.1114(2) 0.4555(3) 0.0170(7) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C11 1.801(3) . ?
Mn1 C12 1.809(4) . ?
Mn1 C13 1.820(3) . ?
Mn1 N2 2.019(3) . ?
Mn1 N4 2.034(3) . ?
Mn1 N1 2.115(3) . ?
O1 C11 1.147(4) . ?
O2 C12 1.150(4) . ?
O3 C13 1.148(4) . ?
N1 C6 1.487(4) . ?
N1 C1 1.489(4) . ?
N1 H1 1.0000 . ?
N2 C2 1.294(4) . ?
N2 C3 1.481(4) . ?
N3 C2 1.351(4) . ?
N3 C5 1.456(4) . ?
N3 C4 1.468(4) . ?
N4 C7 1.287(4) . ?
N4 C8 1.474(4) . ?
N5 C7 1.348(4) . ?
N5 C10 1.445(4) . ?
N5 C9 1.471(4) . ?
C1 C2 1.494(4) . ?
C1 H2 0.9900 . ?
C1 H3 0.9900 . ?
C3 C4 1.534(5) . ?
C3 H4 0.9900 . ?
C3 H5 0.9900 . ?
C4 H6 0.9900 . ?
C4 H7 0.9900 . ?
C5 H8 0.9800 . ?
C5 H9 0.9800 . ?
C5 H10 0.9800 . ?
C6 C7 1.497(4) . ?
C6 H11 0.9900 . ?
C6 H12 0.9900 . ?
C8 C9 1.541(4) . ?
C8 H13 0.9900 . ?
C8 H14 0.9900 . ?
C9 H15 0.9900 . ?
C9 H16 0.9900 . ?
C10 H17 0.9800 . ?
C10 H18 0.9800 . ?
C10 H19 0.9800 . ?

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
C11 Mn1 C12 90.35(14) . . ?
C11 Mn1 C13 91.09(14) . . ?
C12 Mn1 C13 89.92(15) . . ?
C11 Mn1 N2 95.91(13) . . ?
C12 Mn1 N2 173.70(13) . . ?
C13 Mn1 N2 90.69(13) . . ?
C11 Mn1 N4 94.12(12) . . ?
C12 Mn1 N4 92.70(12) . . ?
C13 Mn1 N4 174.15(13) . . ?
N2 Mn1 N4 86.13(10) . . ?
C11 Mn1 N1 171.51(12) . . ?
C12 Mn1 N1 93.78(12) . . ?
C13 Mn1 N1 96.33(12) . . ?
N2 Mn1 N1 79.92(10) . . ?
N4 Mn1 N1 78.29(10) . . ?
C6 N1 C1 112.1(2) . . ?
C6 N1 Mn1 108.39(18) . . ?
C1 N1 Mn1 111.93(19) . . ?
C6 N1 H1 108.1 . . ?
C1 N1 H1 108.1 . . ?
Mn1 N1 H1 108.1 . . ?
C2 N2 C3 107.2(3) . . ?
C2 N2 Mn1 117.7(2) . . ?
C3 N2 Mn1 135.0(2) . . ?
C2 N3 C5 124.1(3) . . ?
C2 N3 C4 106.4(3) . . ?
C5 N3 C4 120.5(3) . . ?
C7 N4 C8 108.1(3) . . ?
C7 N4 Mn1 116.5(2) . . ?
C8 N4 Mn1 135.2(2) . . ?
C7 N5 C10 126.5(3) . . ?
C7 N5 C9 107.9(3) . . ?
C10 N5 C9 120.7(3) . . ?
N1 C1 C2 109.6(3) . . ?
N1 C1 H2 109.7 . . ?
C2 C1 H2 109.7 . . ?
N1 C1 H3 109.7 . . ?
C2 C1 H3 109.7 . . ?
H2 C1 H3 108.2 . . ?
N2 C2 N3 116.2(3) . . ?
N2 C2 C1 119.2(3) . . ?
N3 C2 C1 124.5(3) . . ?
N2 C3 C4 103.8(3) . . ?
N2 C3 H4 111.0 . . ?
C4 C3 H4 111.0 . . ?
N2 C3 H5 111.0 . . ?
C4 C3 H5 111.0 . . ?
H4 C3 H5 109.0 . . ?
N3 C4 C3 102.3(3) . . ?
N3 C4 H6 111.3 . . ?
C3 C4 H6 111.3 . . ?
N3 C4 H7 111.3 . . ?
C3 C4 H7 111.3 . . ?
H6 C4 H7 109.2 . . ?
N3 C5 H8 109.5 . . ?
N3 C5 H9 109.5 . . ?
H8 C5 H9 109.5 . . ?
N3 C5 H10 109.5 . . ?
H8 C5 H10 109.5 . . ?
H9 C5 H10 109.5 . . ?
N1 C6 C7 106.8(2) . . ?
N1 C6 H11 110.4 . . ?
C7 C6 H11 110.4 . . ?
N1 C6 H12 110.4 . . ?
C7 C6 H12 110.4 . . ?
H11 C6 H12 108.6 . . ?
N4 C7 N5 116.0(3) . . ?
N4 C7 C6 118.1(3) . . ?
N5 C7 C6 125.9(3) . . ?
N4 C8 C9 104.5(3) . . ?
N4 C8 H13 110.8 . . ?
C9 C8 H13 110.8 . . ?
N4 C8 H14 110.8 . . ?
C9 C8 H14 110.8 . . ?
H13 C8 H14 108.9 . . ?
N5 C9 C8 102.1(2) . . ?
N5 C9 H15 111.3 . . ?
C8 C9 H15 111.3 . . ?
N5 C9 H16 111.3 . . ?
C8 C9 H16 111.3 . . ?
H15 C9 H16 109.2 . . ?
N5 C10 H17 109.5 . . ?
N5 C10 H18 109.5 . . ?
H17 C10 H18 109.5 . . ?
N5 C10 H19 109.5 . . ?
H17 C10 H19 109.5 . . ?
H18 C10 H19 109.5 . . ?
O1 C11 Mn1 178.3(3) . . ?
O2 C12 Mn1 178.2(3) . . ?
O3 C13 Mn1 177.4(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C1 C2 -109.0(3) . . . . ?
Mn1 N1 C1 C2 13.1(3) . . . . ?
C3 N2 C2 N3 2.1(4) . . . . ?
Mn1 N2 C2 N3 -174.4(2) . . . . ?
C3 N2 C2 C1 -176.5(3) . . . . ?
Mn1 N2 C2 C1 7.1(4) . . . . ?
C5 N3 C2 N2 -161.6(3) . . . . ?
C4 N3 C2 N2 -14.7(4) . . . . ?
C5 N3 C2 C1 16.9(5) . . . . ?
C4 N3 C2 C1 163.8(3) . . . . ?
N1 C1 C2 N2 -13.5(4) . . . . ?
N1 C1 C2 N3 168.0(3) . . . . ?
C2 N2 C3 C4 10.8(3) . . . . ?
Mn1 N2 C3 C4 -173.7(2) . . . . ?
C2 N3 C4 C3 19.7(3) . . . . ?
C5 N3 C4 C3 168.0(3) . . . . ?
N2 C3 C4 N3 -18.2(3) . . . . ?
C1 N1 C6 C7 88.0(3) . . . . ?
Mn1 N1 C6 C7 -36.1(3) . . . . ?
C8 N4 C7 N5 -0.6(4) . . . . ?
Mn1 N4 C7 N5 175.2(2) . . . . ?
C8 N4 C7 C6 -179.5(3) . . . . ?
Mn1 N4 C7 C6 -3.7(4) . . . . ?
C10 N5 C7 N4 163.0(3) . . . . ?
C9 N5 C7 N4 7.9(4) . . . . ?
C10 N5 C7 C6 -18.2(5) . . . . ?
C9 N5 C7 C6 -173.2(3) . . . . ?
N1 C6 C7 N4 27.5(4) . . . . ?
N1 C6 C7 N5 -151.4(3) . . . . ?
C7 N4 C8 C9 -6.6(3) . . . . ?
Mn1 N4 C8 C9 178.8(2) . . . . ?
C7 N5 C9 C8 -11.0(3) . . . . ?
C10 N5 C9 C8 -167.7(3) . . . . ?
N4 C8 C9 N5 10.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 Br1 . . . 3.265(3) 1.000 2.302 161.2 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_C15H23N5O3BrMn
_database_code_depnum_ccdc_archive 'CCDC 2248414'
loop_
_audit_author_name
_audit_author_address
'Yoshihito Kayaki'
;Tokyo Institute of Technology
Japan
;
_audit_update_record             
;
2023-09-20 deposited with the CCDC.	2023-09-21 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C15 H23 Br Mn N5 O3'
_chemical_formula_moiety         'C15 H23 Mn N5 O3, Br'
_chemical_formula_weight         456.22
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'C m c 21'
_space_group_name_Hall           'C 2c -2'
_space_group_IT_number           36
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,+Y,+Z
3 -X,-Y,1/2+Z
4 +X,-Y,1/2+Z
5 1/2+X,1/2+Y,+Z
6 1/2-X,1/2+Y,+Z
7 1/2-X,1/2-Y,1/2+Z
8 1/2+X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   16.301(3)
_cell_length_b                   14.358(2)
_cell_length_c                   7.9184(11)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1853.3(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3323
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      27.49
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928.00
_exptl_absorpt_coefficient_mu    2.899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.599
_exptl_absorpt_correction_T_max  0.865

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            7474
_diffrn_reflns_av_unetI/netI     0.0984
_diffrn_reflns_av_R_equivalents  0.0700
_diffrn_reflns_theta_max         27.449
_diffrn_reflns_theta_min         3.193
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2181
_reflns_number_gt                1864
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.859
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.999

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1000
_refine_ls_wR_factor_gt          0.0996
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2181
_refine_ls_number_parameters     122
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0364P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         1.67
_refine_diff_density_min         -0.53
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 734 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.006(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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Mn Mn 0.3368 0.7283
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 1.0000 0.61776(6) 0.94806(11) 0.0196(3) Uani 1 2 d S T P . .
Mn1 Mn 1.0000 0.81794(10) 0.37502(18) 0.0127(3) Uani 1 2 d S T P . .
O1 O 1.0000 1.0186(4) 0.4469(11) 0.0255(15) Uani 1 2 d S T P . .
O2 O 0.8737(3) 0.8564(4) 0.1180(6) 0.0258(13) Uani 1 1 d . . . . .
N1 N 1.0000 0.6758(5) 0.3472(10) 0.0134(17) Uani 1 2 d S T P . .
H1 H 1.0000 0.6619 0.2234 0.016 Uiso 1 2 calc R U P . .
N2 N 0.9134(3) 0.7830(4) 0.5525(6) 0.0133(12) Uani 1 1 d . . . . .
N3 N 0.8298(4) 0.6618(4) 0.6555(7) 0.0170(13) Uani 1 1 d . . . . .
C1 C 0.9244(4) 0.6350(4) 0.4203(9) 0.0148(16) Uani 1 1 d . . . . .
H2 H 0.9374 0.5737 0.4710 0.018 Uiso 1 1 calc R U . . .
H3 H 0.8836 0.6250 0.3295 0.018 Uiso 1 1 calc R U . . .
C2 C 0.8886(4) 0.6976(5) 0.5527(8) 0.0126(14) Uani 1 1 d . . . . .
C3 C 0.8805(4) 0.8487(5) 0.6770(10) 0.0193(16) Uani 1 1 d . . . . .
H4 H 0.8759 0.9111 0.6245 0.023 Uiso 1 1 calc R U . . .
H5 H 0.9192 0.8535 0.7729 0.023 Uiso 1 1 calc R U . . .
C4 C 0.7969(4) 0.8193(5) 0.7429(9) 0.0186(16) Uani 1 1 d . . . . .
H6 H 0.7814 0.8588 0.8403 0.022 Uiso 1 1 calc R U . . .
H7 H 0.7551 0.8275 0.6534 0.022 Uiso 1 1 calc R U . . .
C5 C 0.8002(4) 0.7187(5) 0.7965(8) 0.0199(16) Uani 1 1 d . . . . .
H8 H 0.8374 0.7118 0.8944 0.024 Uiso 1 1 calc R U . . .
H9 H 0.7448 0.6976 0.8308 0.024 Uiso 1 1 calc R U . . .
C6 C 0.8169(5) 0.5624(5) 0.6710(9) 0.0238(17) Uani 1 1 d . . . . .
H10 H 0.8613 0.5350 0.7381 0.036 Uiso 1 1 calc R U . . .
H11 H 0.8164 0.5340 0.5584 0.036 Uiso 1 1 calc R U . . .
H12 H 0.7642 0.5507 0.7269 0.036 Uiso 1 1 calc R U . . .
C7 C 1.0000 0.9412(6) 0.4177(11) 0.011(2) Uani 1 2 d S T P . .
C8 C 0.9229(4) 0.8384(5) 0.2171(9) 0.0149(15) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C8 1.797(7) 2_755 ?
Mn1 C8 1.797(7) . ?
Mn1 C7 1.802(9) . ?
Mn1 N1 2.052(7) . ?
Mn1 N2 2.054(5) 2_755 ?
Mn1 N2 2.054(5) . ?
O1 C7 1.135(10) . ?
O2 C8 1.151(8) . ?
N1 C1 1.482(7) . ?
N1 C1 1.483(7) 2_755 ?
N1 H1 1.0000 . ?
N2 C2 1.291(8) . ?
N2 C3 1.466(9) . ?
N3 C2 1.359(8) . ?
N3 C6 1.449(9) . ?
N3 C5 1.464(8) . ?
C1 C2 1.500(9) . ?
C1 H2 0.9900 . ?
C1 H3 0.9900 . ?
C3 C4 1.519(9) . ?
C3 H4 0.9900 . ?
C3 H5 0.9900 . ?
C4 C5 1.507(9) . ?
C4 H6 0.9900 . ?
C4 H7 0.9900 . ?
C5 H8 0.9900 . ?
C5 H9 0.9900 . ?
C6 H10 0.9800 . ?
C6 H11 0.9800 . ?
C6 H12 0.9800 . ?

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
C8 Mn1 C8 88.8(4) 2_755 . ?
C8 Mn1 C7 88.3(3) 2_755 . ?
C8 Mn1 C7 88.3(3) . . ?
C8 Mn1 N1 95.0(3) 2_755 . ?
C8 Mn1 N1 95.0(3) . . ?
C7 Mn1 N1 175.4(4) . . ?
C8 Mn1 N2 92.0(2) 2_755 2_755 ?
C8 Mn1 N2 175.3(3) . 2_755 ?
C7 Mn1 N2 96.4(3) . 2_755 ?
N1 Mn1 N2 80.3(2) . 2_755 ?
C8 Mn1 N2 175.3(3) 2_755 . ?
C8 Mn1 N2 92.0(2) . . ?
C7 Mn1 N2 96.4(3) . . ?
N1 Mn1 N2 80.3(2) . . ?
N2 Mn1 N2 86.8(3) 2_755 . ?
C1 N1 C1 112.5(7) . 2_755 ?
C1 N1 Mn1 110.6(4) . . ?
C1 N1 Mn1 110.6(4) 2_755 . ?
C1 N1 H1 107.7 . . ?
C1 N1 H1 107.7 2_755 . ?
Mn1 N1 H1 107.7 . . ?
C2 N2 C3 119.7(6) . . ?
C2 N2 Mn1 116.6(4) . . ?
C3 N2 Mn1 123.7(5) . . ?
C2 N3 C6 121.7(6) . . ?
C2 N3 C5 118.6(6) . . ?
C6 N3 C5 116.0(5) . . ?
N1 C1 C2 111.1(5) . . ?
N1 C1 H2 109.4 . . ?
C2 C1 H2 109.4 . . ?
N1 C1 H3 109.4 . . ?
C2 C1 H3 109.4 . . ?
H2 C1 H3 108.0 . . ?
N2 C2 N3 125.5(6) . . ?
N2 C2 C1 116.5(6) . . ?
N3 C2 C1 117.8(6) . . ?
N2 C3 C4 112.4(6) . . ?
N2 C3 H4 109.1 . . ?
C4 C3 H4 109.1 . . ?
N2 C3 H5 109.1 . . ?
C4 C3 H5 109.1 . . ?
H4 C3 H5 107.9 . . ?
C5 C4 C3 109.4(5) . . ?
C5 C4 H6 109.8 . . ?
C3 C4 H6 109.8 . . ?
C5 C4 H7 109.8 . . ?
C3 C4 H7 109.8 . . ?
H6 C4 H7 108.3 . . ?
N3 C5 C4 109.4(5) . . ?
N3 C5 H8 109.8 . . ?
C4 C5 H8 109.8 . . ?
N3 C5 H9 109.8 . . ?
C4 C5 H9 109.8 . . ?
H8 C5 H9 108.2 . . ?
N3 C6 H10 109.5 . . ?
N3 C6 H11 109.5 . . ?
H10 C6 H11 109.5 . . ?
N3 C6 H12 109.5 . . ?
H10 C6 H12 109.5 . . ?
H11 C6 H12 109.5 . . ?
O1 C7 Mn1 179.1(9) . . ?
O2 C8 Mn1 176.4(7) . . ?

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
C1 N1 C1 C2 100.0(7) 2_755 . . . ?
Mn1 N1 C1 C2 -24.1(7) . . . . ?
C3 N2 C2 N3 3.5(9) . . . . ?
Mn1 N2 C2 N3 -177.4(5) . . . . ?
C3 N2 C2 C1 179.3(6) . . . . ?
Mn1 N2 C2 C1 -1.6(7) . . . . ?
C6 N3 C2 N2 -167.7(6) . . . . ?
C5 N3 C2 N2 -10.4(9) . . . . ?
C6 N3 C2 C1 16.6(9) . . . . ?
C5 N3 C2 C1 173.8(6) . . . . ?
N1 C1 C2 N2 17.3(8) . . . . ?
N1 C1 C2 N3 -166.5(5) . . . . ?
C2 N2 C3 C4 -24.0(8) . . . . ?
Mn1 N2 C3 C4 157.0(4) . . . . ?
N2 C3 C4 C5 49.5(8) . . . . ?
C2 N3 C5 C4 36.6(8) . . . . ?
C6 N3 C5 C4 -164.9(5) . . . . ?
C3 C4 C5 N3 -54.8(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 Br1 . . 1_554 3.269(8) 1.000 2.271 175.3 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_C17H27N5O3BrMn
_database_code_depnum_ccdc_archive 'CCDC 2248413'
loop_
_audit_author_name
_audit_author_address
'Yoshihito Kayaki'
;Tokyo Institute of Technology
Japan
;
_audit_update_record             
;
2023-09-20 deposited with the CCDC.	2023-09-21 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C17 H27 Br Mn N5 O3'
_chemical_formula_moiety         'C17 H27 Mn N5 O3, Br'
_chemical_formula_weight         484.27
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   10.835(2)
_cell_length_b                   18.242(3)
_cell_length_c                   10.958(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 103.653(3)
_cell_angle_gamma                90.0000
_cell_volume                     2104.6(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5809
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      27.49
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992.00
_exptl_absorpt_coefficient_mu    2.558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.625
_exptl_absorpt_correction_T_max  0.858

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            17194
_diffrn_reflns_av_unetI/netI     0.0874
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_min         3.025
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4813
_reflns_number_gt                3075
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0901
_refine_ls_wR_factor_gt          0.0859
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4813
_refine_ls_number_parameters     248
_refine_ls_goodness_of_fit_ref   0.892
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0402P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         1.09
_refine_diff_density_min         -0.46
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Mn Mn 0.3368 0.7283
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.33068(3) -0.09839(2) 0.60642(3) 0.01971(10) Uani 1 1 d . . . . .
Mn1 Mn 0.33654(4) 0.22998(2) 0.46275(4) 0.01219(12) Uani 1 1 d . . . . .
O1 O 0.1903(2) 0.36740(12) 0.4111(2) 0.0259(6) Uani 1 1 d . . . . .
O2 O 0.5750(2) 0.31209(12) 0.5618(2) 0.0240(6) Uani 1 1 d . . . . .
O3 O 0.3922(2) 0.25248(12) 0.2138(2) 0.0258(6) Uani 1 1 d . . . . .
N1 N 0.4187(2) 0.12534(12) 0.5006(2) 0.0109(5) Uani 1 1 d . . . . .
H1 H 0.5025 0.1263 0.4772 0.013 Uiso 1 1 calc R U . . .
N2 N 0.1830(2) 0.16586(13) 0.3937(2) 0.0135(6) Uani 1 1 d . . . . .
N3 N 0.1003(2) 0.05393(13) 0.3476(2) 0.0134(6) Uani 1 1 d . . . . .
N4 N 0.3032(2) 0.20913(13) 0.6331(2) 0.0133(6) Uani 1 1 d . . . . .
N5 N 0.3444(3) 0.14598(13) 0.8129(2) 0.0183(6) Uani 1 1 d . . . . .
C1 C 0.3375(3) 0.06967(16) 0.4190(3) 0.0124(6) Uani 1 1 d . . . . .
H2 H 0.3682 0.0619 0.3418 0.015 Uiso 1 1 calc R U . . .
H3 H 0.3422 0.0224 0.4642 0.015 Uiso 1 1 calc R U . . .
C2 C 0.2038(3) 0.09627(16) 0.3855(3) 0.0108(6) Uani 1 1 d . . . . .
C3 C 0.0447(3) 0.17674(16) 0.3620(3) 0.0158(7) Uani 1 1 d . . . . .
H4 H 0.0201 0.2168 0.3001 0.019 Uiso 1 1 calc R U . . .
H5 H 0.0141 0.1887 0.4380 0.019 Uiso 1 1 calc R U . . .
C4 C -0.0099(3) 0.10285(16) 0.3057(3) 0.0153(7) Uani 1 1 d . . . . .
H6 H -0.0827 0.0872 0.3397 0.018 Uiso 1 1 calc R U . . .
H7 H -0.0369 0.1052 0.2130 0.018 Uiso 1 1 calc R U . . .
C5 C 0.4436(3) 0.10748(16) 0.6369(3) 0.0135(6) Uani 1 1 d . . . . .
H8 H 0.5340 0.1166 0.6775 0.016 Uiso 1 1 calc R U . . .
H9 H 0.4252 0.0551 0.6479 0.016 Uiso 1 1 calc R U . . .
C6 C 0.3608(3) 0.15433(16) 0.6963(3) 0.0119(6) Uani 1 1 d . . . . .
C7 C 0.2286(3) 0.24662(17) 0.7118(3) 0.0182(7) Uani 1 1 d . . . . .
H10 H 0.1371 0.2465 0.6699 0.022 Uiso 1 1 calc R U . . .
H11 H 0.2572 0.2980 0.7284 0.022 Uiso 1 1 calc R U . . .
C8 C 0.2537(3) 0.20233(16) 0.8342(3) 0.0178(7) Uani 1 1 d . . . . .
H12 H 0.2915 0.2334 0.9076 0.021 Uiso 1 1 calc R U . . .
H13 H 0.1746 0.1798 0.8470 0.021 Uiso 1 1 calc R U . . .
C9 C 0.1012(3) -0.02264(16) 0.3062(3) 0.0156(7) Uani 1 1 d . . . . .
H14 H 0.1866 -0.0437 0.3450 0.019 Uiso 1 1 calc R U . . .
C10 C 0.0813(4) -0.02719(19) 0.1635(3) 0.0253(8) Uani 1 1 d . . . . .
H15 H -0.0005 -0.0049 0.1231 0.038 Uiso 1 1 calc R U . . .
H16 H 0.0817 -0.0787 0.1381 0.038 Uiso 1 1 calc R U . . .
H17 H 0.1498 -0.0009 0.1378 0.038 Uiso 1 1 calc R U . . .
C11 C 0.0023(3) -0.06650(17) 0.3538(3) 0.0211(7) Uani 1 1 d . . . . .
H18 H -0.0827 -0.0483 0.3140 0.032 Uiso 1 1 calc R U . . .
H19 H 0.0175 -0.0610 0.4451 0.032 Uiso 1 1 calc R U . . .
H20 H 0.0086 -0.1184 0.3328 0.032 Uiso 1 1 calc R U . . .
C12 C 0.3927(3) 0.08729(16) 0.9024(3) 0.0146(7) Uani 1 1 d . . . . .
H21 H 0.4686 0.0655 0.8788 0.018 Uiso 1 1 calc R U . . .
C13 C 0.4362(4) 0.11771(19) 1.0338(3) 0.0270(8) Uani 1 1 d . . . . .
H22 H 0.4822 0.0797 1.0897 0.041 Uiso 1 1 calc R U . . .
H23 H 0.3621 0.1334 1.0640 0.041 Uiso 1 1 calc R U . . .
H24 H 0.4923 0.1597 1.0331 0.041 Uiso 1 1 calc R U . . .
C14 C 0.2953(3) 0.02614(18) 0.8968(3) 0.0248(8) Uani 1 1 d . . . . .
H25 H 0.3297 -0.0111 0.9601 0.037 Uiso 1 1 calc R U . . .
H26 H 0.2763 0.0037 0.8132 0.037 Uiso 1 1 calc R U . . .
H27 H 0.2172 0.0466 0.9135 0.037 Uiso 1 1 calc R U . . .
C15 C 0.2485(3) 0.31385(17) 0.4345(3) 0.0165(7) Uani 1 1 d . . . . .
C16 C 0.4822(3) 0.27901(16) 0.5267(3) 0.0162(7) Uani 1 1 d . . . . .
C17 C 0.3704(3) 0.24056(16) 0.3098(3) 0.0160(7) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C15 1.791(3) . ?
Mn1 C16 1.805(3) . ?
Mn1 C17 1.808(3) . ?
Mn1 N4 2.020(3) . ?
Mn1 N2 2.028(3) . ?
Mn1 N1 2.106(2) . ?
O1 C15 1.158(4) . ?
O2 C16 1.157(4) . ?
O3 C17 1.153(4) . ?
N1 C5 1.489(4) . ?
N1 C1 1.494(4) . ?
N1 H1 1.0000 . ?
N2 C2 1.296(4) . ?
N2 C3 1.470(4) . ?
N3 C2 1.344(4) . ?
N3 C9 1.469(4) . ?
N3 C4 1.475(4) . ?
N4 C6 1.290(4) . ?
N4 C7 1.480(4) . ?
N5 C6 1.340(4) . ?
N5 C12 1.463(4) . ?
N5 C8 1.478(4) . ?
C1 C2 1.489(4) . ?
C1 H2 0.9900 . ?
C1 H3 0.9900 . ?
C3 C4 1.541(4) . ?
C3 H4 0.9900 . ?
C3 H5 0.9900 . ?
C4 H6 0.9900 . ?
C4 H7 0.9900 . ?
C5 C6 1.495(4) . ?
C5 H8 0.9900 . ?
C5 H9 0.9900 . ?
C7 C8 1.534(4) . ?
C7 H10 0.9900 . ?
C7 H11 0.9900 . ?
C8 H12 0.9900 . ?
C8 H13 0.9900 . ?
C9 C11 1.524(4) . ?
C9 C10 1.530(4) . ?
C9 H14 1.0000 . ?
C10 H15 0.9800 . ?
C10 H16 0.9800 . ?
C10 H17 0.9800 . ?
C11 H18 0.9800 . ?
C11 H19 0.9800 . ?
C11 H20 0.9800 . ?
C12 C13 1.511(4) . ?
C12 C14 1.527(4) . ?
C12 H21 1.0000 . ?
C13 H22 0.9800 . ?
C13 H23 0.9800 . ?
C13 H24 0.9800 . ?
C14 H25 0.9800 . ?
C14 H26 0.9800 . ?
C14 H27 0.9800 . ?

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
C15 Mn1 C16 91.43(14) . . ?
C15 Mn1 C17 87.99(14) . . ?
C16 Mn1 C17 87.54(14) . . ?
C15 Mn1 N4 96.68(12) . . ?
C16 Mn1 N4 93.74(12) . . ?
C17 Mn1 N4 175.12(12) . . ?
C15 Mn1 N2 94.12(12) . . ?
C16 Mn1 N2 174.45(12) . . ?
C17 Mn1 N2 92.52(12) . . ?
N4 Mn1 N2 85.76(10) . . ?
C15 Mn1 N1 172.61(12) . . ?
C16 Mn1 N1 94.72(12) . . ?
C17 Mn1 N1 96.35(11) . . ?
N4 Mn1 N1 78.86(10) . . ?
N2 Mn1 N1 79.76(10) . . ?
C5 N1 C1 113.1(2) . . ?
C5 N1 Mn1 111.34(17) . . ?
C1 N1 Mn1 109.65(18) . . ?
C5 N1 H1 107.5 . . ?
C1 N1 H1 107.5 . . ?
Mn1 N1 H1 107.5 . . ?
C2 N2 C3 107.5(2) . . ?
C2 N2 Mn1 116.7(2) . . ?
C3 N2 Mn1 135.32(19) . . ?
C2 N3 C9 125.2(3) . . ?
C2 N3 C4 107.7(2) . . ?
C9 N3 C4 122.9(2) . . ?
C6 N4 C7 107.8(2) . . ?
C6 N4 Mn1 118.2(2) . . ?
C7 N4 Mn1 133.8(2) . . ?
C6 N5 C12 128.0(2) . . ?
C6 N5 C8 108.3(2) . . ?
C12 N5 C8 123.3(2) . . ?
C2 C1 N1 109.1(2) . . ?
C2 C1 H2 109.9 . . ?
N1 C1 H2 109.9 . . ?
C2 C1 H3 109.9 . . ?
N1 C1 H3 109.9 . . ?
H2 C1 H3 108.3 . . ?
N2 C2 N3 116.0(3) . . ?
N2 C2 C1 118.5(3) . . ?
N3 C2 C1 125.5(3) . . ?
N2 C3 C4 104.5(2) . . ?
N2 C3 H4 110.9 . . ?
C4 C3 H4 110.9 . . ?
N2 C3 H5 110.9 . . ?
C4 C3 H5 110.9 . . ?
H4 C3 H5 108.9 . . ?
N3 C4 C3 101.4(2) . . ?
N3 C4 H6 111.5 . . ?
C3 C4 H6 111.5 . . ?
N3 C4 H7 111.5 . . ?
C3 C4 H7 111.5 . . ?
H6 C4 H7 109.3 . . ?
N1 C5 C6 109.1(2) . . ?
N1 C5 H8 109.9 . . ?
C6 C5 H8 109.9 . . ?
N1 C5 H9 109.9 . . ?
C6 C5 H9 109.9 . . ?
H8 C5 H9 108.3 . . ?
N4 C6 N5 116.4(3) . . ?
N4 C6 C5 118.2(3) . . ?
N5 C6 C5 125.4(3) . . ?
N4 C7 C8 104.9(2) . . ?
N4 C7 H10 110.8 . . ?
C8 C7 H10 110.8 . . ?
N4 C7 H11 110.8 . . ?
C8 C7 H11 110.8 . . ?
H10 C7 H11 108.8 . . ?
N5 C8 C7 102.4(2) . . ?
N5 C8 H12 111.3 . . ?
C7 C8 H12 111.3 . . ?
N5 C8 H13 111.3 . . ?
C7 C8 H13 111.3 . . ?
H12 C8 H13 109.2 . . ?
N3 C9 C11 109.7(2) . . ?
N3 C9 C10 110.9(2) . . ?
C11 C9 C10 112.3(3) . . ?
N3 C9 H14 107.9 . . ?
C11 C9 H14 107.9 . . ?
C10 C9 H14 107.9 . . ?
C9 C10 H15 109.5 . . ?
C9 C10 H16 109.5 . . ?
H15 C10 H16 109.5 . . ?
C9 C10 H17 109.5 . . ?
H15 C10 H17 109.5 . . ?
H16 C10 H17 109.5 . . ?
C9 C11 H18 109.5 . . ?
C9 C11 H19 109.5 . . ?
H18 C11 H19 109.5 . . ?
C9 C11 H20 109.5 . . ?
H18 C11 H20 109.5 . . ?
H19 C11 H20 109.5 . . ?
N5 C12 C13 110.6(3) . . ?
N5 C12 C14 111.9(3) . . ?
C13 C12 C14 111.3(3) . . ?
N5 C12 H21 107.6 . . ?
C13 C12 H21 107.6 . . ?
C14 C12 H21 107.6 . . ?
C12 C13 H22 109.5 . . ?
C12 C13 H23 109.5 . . ?
H22 C13 H23 109.5 . . ?
C12 C13 H24 109.5 . . ?
H22 C13 H24 109.5 . . ?
H23 C13 H24 109.5 . . ?
C12 C14 H25 109.5 . . ?
C12 C14 H26 109.5 . . ?
H25 C14 H26 109.5 . . ?
C12 C14 H27 109.5 . . ?
H25 C14 H27 109.5 . . ?
H26 C14 H27 109.5 . . ?
O1 C15 Mn1 177.2(3) . . ?
O2 C16 Mn1 176.5(3) . . ?
O3 C17 Mn1 175.3(3) . . ?

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
C5 N1 C1 C2 98.3(3) . . . . ?
Mn1 N1 C1 C2 -26.6(3) . . . . ?
C3 N2 C2 N3 2.4(4) . . . . ?
Mn1 N2 C2 N3 175.72(19) . . . . ?
C3 N2 C2 C1 -177.2(2) . . . . ?
Mn1 N2 C2 C1 -3.8(4) . . . . ?
C9 N3 C2 N2 166.4(3) . . . . ?
C4 N3 C2 N2 9.1(3) . . . . ?
C9 N3 C2 C1 -14.1(4) . . . . ?
C4 N3 C2 C1 -171.4(3) . . . . ?
N1 C1 C2 N2 20.9(4) . . . . ?
N1 C1 C2 N3 -158.5(3) . . . . ?
C2 N2 C3 C4 -12.1(3) . . . . ?
Mn1 N2 C3 C4 176.3(2) . . . . ?
C2 N3 C4 C3 -15.4(3) . . . . ?
C9 N3 C4 C3 -173.3(2) . . . . ?
N2 C3 C4 N3 16.3(3) . . . . ?
C1 N1 C5 C6 -102.7(3) . . . . ?
Mn1 N1 C5 C6 21.3(3) . . . . ?
C7 N4 C6 N5 -2.1(4) . . . . ?
Mn1 N4 C6 N5 174.6(2) . . . . ?
C7 N4 C6 C5 -179.7(3) . . . . ?
Mn1 N4 C6 C5 -3.0(4) . . . . ?
C12 N5 C6 N4 176.7(3) . . . . ?
C8 N5 C6 N4 3.7(4) . . . . ?
C12 N5 C6 C5 -5.8(5) . . . . ?
C8 N5 C6 C5 -178.9(3) . . . . ?
N1 C5 C6 N4 -12.7(4) . . . . ?
N1 C5 C6 N5 169.9(3) . . . . ?
C6 N4 C7 C8 -0.3(3) . . . . ?
Mn1 N4 C7 C8 -176.3(2) . . . . ?
C6 N5 C8 C7 -3.4(3) . . . . ?
C12 N5 C8 C7 -176.8(3) . . . . ?
N4 C7 C8 N5 2.2(3) . . . . ?
C2 N3 C9 C11 141.7(3) . . . . ?
C4 N3 C9 C11 -64.3(4) . . . . ?
C2 N3 C9 C10 -93.6(3) . . . . ?
C4 N3 C9 C10 60.4(4) . . . . ?
C6 N5 C12 C13 140.5(3) . . . . ?
C8 N5 C12 C13 -47.3(4) . . . . ?
C6 N5 C12 C14 -94.8(4) . . . . ?
C8 N5 C12 C14 77.3(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 Br1 . . 3_656 3.239(3) 1.000 2.269 163.2 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


