# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_ax1527_sq
_database_code_depnum_ccdc_archive 'CCDC 1922221'
loop_
_audit_author_name
_audit_author_address
'Anke Spannenberg'
;LIKAT
Germany
;
_audit_update_record             
;
2019-06-11 deposited with the CCDC.	2019-10-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 Mn N3 O5'
_chemical_formula_weight         331.17

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'

_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                   7.5940(14)
_cell_length_b                   8.5623(16)
_cell_length_c                   13.088(3)
_cell_angle_alpha                97.266(3)
_cell_angle_beta                 95.849(3)
_cell_angle_gamma                95.577(3)
_cell_volume                     834.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9875
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      30.50

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.367
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.078
_exptl_absorpt_coefficient_mu    0.811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_T_max  0.79
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            33103
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.579
_diffrn_reflns_theta_max         28.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4438
_reflns_number_gt                4009
_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.
 
 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.
;

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0645P)²+0.3778P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4438
_refine_ls_number_parameters     194
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.1074
_refine_ls_wR_factor_gt          0.1035
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.002
_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
C1 C 0.8217(2) 0.83703(19) 1.00650(13) 0.0278(3) Uani 1 1 d . . . . .
H1 H 0.8730 0.7445 1.0217 0.033 Uiso 1 1 calc R U . . .
C2 C 0.8310(2) 0.9638(2) 1.08432(14) 0.0308(3) Uani 1 1 d . . . . .
H2 H 0.8870 0.9583 1.1519 0.037 Uiso 1 1 calc R U . . .
C3 C 0.7575(2) 1.0985(2) 1.06193(14) 0.0308(3) Uani 1 1 d . . . . .
H3B H 0.7634 1.1875 1.1140 0.037 Uiso 1 1 calc R U . . .
C4 C 0.6751(2) 1.10331(18) 0.96331(14) 0.0286(3) Uani 1 1 d . . . . .
H4 H 0.6236 1.1949 0.9465 0.034 Uiso 1 1 calc R U . . .
C5 C 0.6696(2) 0.97167(17) 0.88999(13) 0.0242(3) Uani 1 1 d . . . . .
C6 C 0.5780(2) 0.95527(19) 0.78450(13) 0.0265(3) Uani 1 1 d . . . . .
C7 C 0.4139(3) 0.9979(3) 0.63798(16) 0.0438(5) Uani 1 1 d . . . . .
H7A H 0.4638 1.0610 0.5872 0.053 Uiso 1 1 calc R U . . .
H7B H 0.2824 0.9941 0.6289 0.053 Uiso 1 1 calc R U . . .
C8 C 0.4735(3) 0.8284(2) 0.62648(14) 0.0382(4) Uani 1 1 d . . . . .
H8A H 0.3692 0.7468 0.6153 0.046 Uiso 1 1 calc R U . . .
H8B H 0.5453 0.8119 0.5678 0.046 Uiso 1 1 calc R U . . .
C9 C 0.9045(3) 0.7027(2) 0.73879(14) 0.0333(4) Uani 1 1 d . . . . .
C10 C 0.8079(2) 0.5089(2) 0.85792(14) 0.0295(3) Uani 1 1 d . . . . .
C11 C 0.6348(3) 0.4994(2) 0.68096(15) 0.0350(4) Uani 1 1 d . . . . .
C12 C 0.3899(2) 0.4884(2) 0.86686(15) 0.0330(4) Uani 1 1 d . . . . .
H12 H 0.2818 0.4922 0.8972 0.040 Uiso 1 1 calc R U . . .
Mn1 Mn 0.69936(3) 0.65259(3) 0.79030(2) 0.02378(8) Uani 1 1 d . . . . .
N1 N 0.74291(17) 0.83967(15) 0.91035(11) 0.0236(3) Uani 1 1 d . . . . .
N2 N 0.5809(2) 0.82257(17) 0.72527(11) 0.0290(3) Uani 1 1 d . . . . .
N3 N 0.4871(3) 1.0622(2) 0.74323(13) 0.0389(4) Uani 1 1 d D . . . .
O1 O 1.0353(2) 0.7314(2) 0.70471(13) 0.0507(4) Uani 1 1 d . . . . .
O2 O 0.8841(2) 0.41866(17) 0.89540(12) 0.0428(3) Uani 1 1 d . . . . .
O3 O 0.5988(3) 0.40341(19) 0.61116(13) 0.0543(4) Uani 1 1 d . . . . .
O4 O 0.46518(16) 0.61917(14) 0.85038(11) 0.0320(3) Uani 1 1 d . . . . .
O5 O 0.4393(3) 0.35803(17) 0.84851(16) 0.0560(4) Uani 1 1 d . . . . .
H3A H 0.473(4) 1.150(2) 0.775(2) 0.054(8) Uiso 1 1 d 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
C1 N1 1.341(2) . ?
C1 C2 1.383(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.381(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(3) . ?
C3 H3B 0.9500 . ?
C4 C5 1.379(2) . ?
C4 H4 0.9500 . ?
C5 N1 1.352(2) . ?
C5 C6 1.465(2) . ?
C6 N2 1.295(2) . ?
C6 N3 1.333(2) . ?
C7 N3 1.450(3) . ?
C7 C8 1.556(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N2 1.465(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 O1 1.147(2) . ?
C9 Mn1 1.7955(19) . ?
C10 O2 1.139(2) . ?
C10 Mn1 1.8165(18) . ?
C11 O3 1.140(2) . ?
C11 Mn1 1.8071(19) . ?
C12 O5 1.215(2) . ?
C12 O4 1.261(2) . ?
C12 H12 0.9500 . ?
Mn1 N2 2.0160(14) . ?
Mn1 O4 2.0262(13) . ?
Mn1 N1 2.0732(14) . ?
N3 H3A 0.835(17) . ?

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 C1 C2 122.48(16) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C3 C2 C1 118.70(17) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 119.66(16) . . ?
C2 C3 H3B 120.2 . . ?
C4 C3 H3B 120.2 . . ?
C5 C4 C3 118.31(15) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
N1 C5 C4 122.72(15) . . ?
N1 C5 C6 112.59(14) . . ?
C4 C5 C6 124.62(15) . . ?
N2 C6 N3 115.95(16) . . ?
N2 C6 C5 117.42(14) . . ?
N3 C6 C5 126.61(15) . . ?
N3 C7 C8 102.58(15) . . ?
N3 C7 H7A 111.3 . . ?
C8 C7 H7A 111.3 . . ?
N3 C7 H7B 111.3 . . ?
C8 C7 H7B 111.3 . . ?
H7A C7 H7B 109.2 . . ?
N2 C8 C7 104.05(15) . . ?
N2 C8 H8A 110.9 . . ?
C7 C8 H8A 110.9 . . ?
N2 C8 H8B 110.9 . . ?
C7 C8 H8B 110.9 . . ?
H8A C8 H8B 109.0 . . ?
O1 C9 Mn1 178.48(17) . . ?
O2 C10 Mn1 175.31(16) . . ?
O3 C11 Mn1 178.08(19) . . ?
O5 C12 O4 127.71(18) . . ?
O5 C12 H12 116.1 . . ?
O4 C12 H12 116.1 . . ?
C9 Mn1 C11 89.70(9) . . ?
C9 Mn1 C10 88.68(8) . . ?
C11 Mn1 C10 88.65(8) . . ?
C9 Mn1 N2 92.26(8) . . ?
C11 Mn1 N2 95.45(7) . . ?
C10 Mn1 N2 175.80(7) . . ?
C9 Mn1 O4 174.35(7) . . ?
C11 Mn1 O4 94.07(7) . . ?
C10 Mn1 O4 95.61(7) . . ?
N2 Mn1 O4 83.20(6) . . ?
C9 Mn1 N1 94.44(7) . . ?
C11 Mn1 N1 172.63(7) . . ?
C10 Mn1 N1 97.52(7) . . ?
N2 Mn1 N1 78.32(6) . . ?
O4 Mn1 N1 81.37(5) . . ?
C1 N1 C5 118.11(14) . . ?
C1 N1 Mn1 126.60(11) . . ?
C5 N1 Mn1 115.03(11) . . ?
C6 N2 C8 108.27(14) . . ?
C6 N2 Mn1 116.50(12) . . ?
C8 N2 Mn1 134.75(12) . . ?
C6 N3 C7 109.06(15) . . ?
C6 N3 H3A 125(2) . . ?
C7 N3 H3A 126(2) . . ?
C12 O4 Mn1 125.98(12) . . ?

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
N1 C1 C2 C3 -0.4(3) . . . . ?
C1 C2 C3 C4 0.6(2) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C3 C4 C5 N1 -0.8(2) . . . . ?
C3 C4 C5 C6 176.11(15) . . . . ?
N1 C5 C6 N2 -1.1(2) . . . . ?
C4 C5 C6 N2 -178.30(15) . . . . ?
N1 C5 C6 N3 177.10(17) . . . . ?
C4 C5 C6 N3 -0.1(3) . . . . ?
N3 C7 C8 N2 -2.9(2) . . . . ?
C2 C1 N1 C5 -0.4(2) . . . . ?
C2 C1 N1 Mn1 -174.17(12) . . . . ?
C4 C5 N1 C1 1.0(2) . . . . ?
C6 C5 N1 C1 -176.23(13) . . . . ?
C4 C5 N1 Mn1 175.51(12) . . . . ?
C6 C5 N1 Mn1 -1.73(16) . . . . ?
N3 C6 N2 C8 -1.7(2) . . . . ?
C5 C6 N2 C8 176.75(15) . . . . ?
N3 C6 N2 Mn1 -174.89(13) . . . . ?
C5 C6 N2 Mn1 3.5(2) . . . . ?
C7 C8 N2 C6 2.8(2) . . . . ?
C7 C8 N2 Mn1 174.26(14) . . . . ?
N2 C6 N3 C7 -0.4(2) . . . . ?
C5 C6 N3 C7 -178.64(17) . . . . ?
C8 C7 N3 C6 2.1(2) . . . . ?
O5 C12 O4 Mn1 -1.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3A O5 0.835(17) 1.966(17) 2.801(2) 180(3) 1_565

_refine_diff_density_max         0.605
_refine_diff_density_min         -0.850
_refine_diff_density_rms         0.070



####################################################################### 
# 
# 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_AX1625
_database_code_depnum_ccdc_archive 'CCDC 1922222'
loop_
_audit_author_name
_audit_author_address
'Anke Spannenberg'
;LIKAT
Germany
;
_audit_update_record             
;
2019-06-11 deposited with the CCDC.	2019-10-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H9 Br Mn N3 O3'
_chemical_formula_weight         366.06

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   7.9845(13)
_cell_length_b                   12.118(2)
_cell_length_c                   14.112(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.181(3)
_cell_angle_gamma                90
_cell_volume                     1344.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9968
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      30.37

_exptl_crystal_description       prism
_exptl_crystal_colour            orange-red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.809
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.287
_exptl_crystal_size_mid          0.193
_exptl_crystal_size_min          0.148
_exptl_absorpt_coefficient_mu    3.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.50
_exptl_absorpt_correction_T_max  0.59
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            34275
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.230
_diffrn_reflns_theta_max         27.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3248
_reflns_number_gt                2922
_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 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0289P)²+0.5027P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3248
_refine_ls_number_parameters     176
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0239
_refine_ls_R_factor_gt           0.0201
_refine_ls_wR_factor_ref         0.0525
_refine_ls_wR_factor_gt          0.0507
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.20749(2) -0.04865(2) 0.16114(2) 0.02695(6) Uani 1 1 d . . . . .
C1 C 0.6511(2) -0.18396(13) 0.16251(11) 0.0223(3) Uani 1 1 d . . . . .
H1A H 0.5460 -0.2258 0.1377 0.027 Uiso 1 1 calc R U . . .
H1B H 0.7148 -0.2228 0.2194 0.027 Uiso 1 1 calc R U . . .
C2 C 0.7619(2) -0.17043(13) 0.08362(11) 0.0234(3) Uani 1 1 d . . . . .
H2B H 0.8841 -0.1818 0.1099 0.028 Uiso 1 1 calc R U . . .
H2C H 0.7263 -0.2220 0.0294 0.028 Uiso 1 1 calc R U . . .
C3 C 0.65212(18) -0.00595(12) 0.12087(11) 0.0188(3) Uani 1 1 d . . . . .
C4 C 0.60544(18) 0.11110(12) 0.12336(10) 0.0182(3) Uani 1 1 d . . . . .
C5 C 0.64814(19) 0.19164(13) 0.06271(11) 0.0216(3) Uani 1 1 d . . . . .
H5 H 0.7162 0.1746 0.0159 0.026 Uiso 1 1 calc R U . . .
C6 C 0.5890(2) 0.29856(13) 0.07184(11) 0.0237(3) Uani 1 1 d . . . . .
H6 H 0.6162 0.3559 0.0312 0.028 Uiso 1 1 calc R U . . .
C7 C 0.4902(2) 0.32006(13) 0.14085(11) 0.0233(3) Uani 1 1 d . . . . .
H7 H 0.4482 0.3923 0.1481 0.028 Uiso 1 1 calc R U . . .
C8 C 0.45313(19) 0.23467(13) 0.19936(11) 0.0216(3) Uani 1 1 d . . . . .
H8 H 0.3845 0.2500 0.2463 0.026 Uiso 1 1 calc R U . . .
C9 C 0.4582(2) -0.12567(14) 0.34815(12) 0.0270(3) Uani 1 1 d . . . . .
C10 C 0.3426(3) 0.07191(15) 0.34975(13) 0.0318(4) Uani 1 1 d . . . . .
C11 C 0.6625(2) 0.03709(13) 0.36546(12) 0.0266(3) Uani 1 1 d . . . . .
Mn1 Mn 0.47727(3) -0.00028(2) 0.28017(2) 0.01957(6) Uani 1 1 d . . . . .
N1 N 0.61089(16) -0.06971(10) 0.18710(9) 0.0200(3) Uani 1 1 d . . . . .
N2 N 0.72648(18) -0.05540(11) 0.05423(10) 0.0248(3) Uani 1 1 d D . . . .
N3 N 0.51004(15) 0.13166(10) 0.19235(9) 0.0182(2) Uani 1 1 d . . . . .
O1 O 0.44913(18) -0.20287(12) 0.39340(10) 0.0417(3) Uani 1 1 d . . . . .
O2 O 0.2573(2) 0.11701(14) 0.39439(12) 0.0557(4) Uani 1 1 d . . . . .
O3 O 0.77863(19) 0.06104(11) 0.42168(11) 0.0418(3) Uani 1 1 d . . . . .
H2A H 0.762(2) -0.0246(15) 0.0072(11) 0.029(5) Uiso 1 1 d 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 2.5546(4) . ?
C1 N1 1.4764(19) . ?
C1 C2 1.548(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N2 1.468(2) . ?
C2 H2B 0.9900 . ?
C2 H2C 0.9900 . ?
C3 N1 1.299(2) . ?
C3 N2 1.339(2) . ?
C3 C4 1.469(2) . ?
C4 N3 1.3611(18) . ?
C4 C5 1.380(2) . ?
C5 C6 1.393(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.382(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.388(2) . ?
C7 H7 0.9500 . ?
C8 N3 1.338(2) . ?
C8 H8 0.9500 . ?
C9 O1 1.142(2) . ?
C9 Mn1 1.8177(17) . ?
C10 O2 1.145(2) . ?
C10 Mn1 1.8051(18) . ?
C11 O3 1.146(2) . ?
C11 Mn1 1.7921(18) . ?
Mn1 N1 2.0167(13) . ?
Mn1 N3 2.0676(13) . ?
N2 H2A 0.851(9) . ?

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 C1 C2 104.21(12) . . ?
N1 C1 H1A 110.9 . . ?
C2 C1 H1A 110.9 . . ?
N1 C1 H1B 110.9 . . ?
C2 C1 H1B 110.9 . . ?
H1A C1 H1B 108.9 . . ?
N2 C2 C1 101.39(12) . . ?
N2 C2 H2B 111.5 . . ?
C1 C2 H2B 111.5 . . ?
N2 C2 H2C 111.5 . . ?
C1 C2 H2C 111.5 . . ?
H2B C2 H2C 109.3 . . ?
N1 C3 N2 116.05(14) . . ?
N1 C3 C4 117.36(13) . . ?
N2 C3 C4 126.50(14) . . ?
N3 C4 C5 123.03(14) . . ?
N3 C4 C3 111.74(13) . . ?
C5 C4 C3 125.22(13) . . ?
C4 C5 C6 118.40(14) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C7 C6 C5 119.05(14) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6 C7 C8 119.14(14) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
N3 C8 C7 122.73(14) . . ?
N3 C8 H8 118.6 . . ?
C7 C8 H8 118.6 . . ?
O1 C9 Mn1 177.82(16) . . ?
O2 C10 Mn1 179.46(17) . . ?
O3 C11 Mn1 178.38(17) . . ?
C11 Mn1 C10 90.70(9) . . ?
C11 Mn1 C9 89.59(7) . . ?
C10 Mn1 C9 90.27(8) . . ?
C11 Mn1 N1 94.25(7) . . ?
C10 Mn1 N1 172.32(7) . . ?
C9 Mn1 N1 95.63(7) . . ?
C11 Mn1 N3 91.74(6) . . ?
C10 Mn1 N3 95.85(7) . . ?
C9 Mn1 N3 173.72(6) . . ?
N1 Mn1 N3 78.15(5) . . ?
C11 Mn1 Br1 178.06(6) . . ?
C10 Mn1 Br1 87.42(7) . . ?
C9 Mn1 Br1 90.91(5) . . ?
N1 Mn1 Br1 87.58(4) . . ?
N3 Mn1 Br1 87.98(4) . . ?
C3 N1 C1 107.18(12) . . ?
C3 N1 Mn1 116.80(10) . . ?
C1 N1 Mn1 134.95(10) . . ?
C3 N2 C2 108.29(13) . . ?
C3 N2 H2A 126.9(14) . . ?
C2 N2 H2A 124.2(14) . . ?
C8 N3 C4 117.64(13) . . ?
C8 N3 Mn1 126.62(10) . . ?
C4 N3 Mn1 115.68(10) . . ?

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
N1 C1 C2 N2 -16.34(15) . . . . ?
N1 C3 C4 N3 -5.58(19) . . . . ?
N2 C3 C4 N3 171.07(14) . . . . ?
N1 C3 C4 C5 175.75(14) . . . . ?
N2 C3 C4 C5 -7.6(2) . . . . ?
N3 C4 C5 C6 -0.8(2) . . . . ?
C3 C4 C5 C6 177.71(14) . . . . ?
C4 C5 C6 C7 0.0(2) . . . . ?
C5 C6 C7 C8 0.2(2) . . . . ?
C6 C7 C8 N3 0.4(2) . . . . ?
N2 C3 N1 C1 -3.94(18) . . . . ?
C4 C3 N1 C1 173.06(12) . . . . ?
N2 C3 N1 Mn1 -173.88(11) . . . . ?
C4 C3 N1 Mn1 3.12(17) . . . . ?
C2 C1 N1 C3 13.00(16) . . . . ?
C2 C1 N1 Mn1 -179.72(11) . . . . ?
N1 C3 N2 C2 -7.64(19) . . . . ?
C4 C3 N2 C2 175.68(14) . . . . ?
C1 C2 N2 C3 14.72(16) . . . . ?
C7 C8 N3 C4 -1.2(2) . . . . ?
C7 C8 N3 Mn1 175.84(11) . . . . ?
C5 C4 N3 C8 1.4(2) . . . . ?
C3 C4 N3 C8 -177.28(13) . . . . ?
C5 C4 N3 Mn1 -175.95(11) . . . . ?
C3 C4 N3 Mn1 5.34(15) . . . . ?

_refine_diff_density_max         0.447
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.058

