# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1902803'
loop_
_audit_author_name
_audit_author_address
'Philip Jeffrey'
;Princeton University
United States of America
;
_audit_update_record             
;
2019-03-12 deposited with the CCDC.	2019-07-23 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            4-OH
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H12 Br Mn N2 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         467.15

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.0073(9)
_cell_length_b                   9.6629(7)
_cell_length_c                   14.7314(10)
_cell_angle_alpha                90
_cell_angle_beta                 117.874(2)
_cell_angle_gamma                90
_cell_volume                     1762.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9305
_cell_measurement_theta_min      2.6248
_cell_measurement_theta_max      36.6793
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       'rectangular prism'
_exptl_crystal_colour            'translucent intense orange-yellow'
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.131
_exptl_crystal_size_min          0.122
_exptl_crystal_density_diffrn    1.760
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928

_exptl_absorpt_coefficient_mu    3.044
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.52
_exptl_absorpt_correction_T_max  0.71

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            98356
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_theta_min         2.63
_diffrn_reflns_theta_max         34.97
_diffrn_reflns_theta_full        34.97
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22

_refine_special_details          
;
;

_reflns_number_total             7721
_reflns_number_gt                6900
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0220
_refine_ls_wR_factor_gt          0.0546
_refine_ls_wR_factor_ref         0.0566
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_number_reflns         7721
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0288P)²+0.6725P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.384
_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 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'

_computing_data_collection       'Bruker Instrument Service v4.2.4'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.28339(2) 0.34323(2) 1.03812(2) 0.01500(3) Uani d . . . 1 . .
N N1 0.23971(6) 0.54543(8) 0.85566(6) 0.01291(13) Uani d . . . 1 . .
O O1 0.59145(6) -0.04485(8) 0.89517(7) 0.02181(15) Uani d . . . 1 . .
C C1 0.20200(8) 0.66995(10) 0.86448(7) 0.01562(16) Uani d . . . 1 . .
H H1 0.131 0.6757 0.8571 0.019 Uiso calc U . R 1 . .
Mn Mn1 0.16542(2) 0.35973(2) 0.84412(2) 0.01253(3) Uani d . . . 1 . .
C C2 0.26230(8) 0.79021(9) 0.88389(7) 0.01664(16) Uani d . . . 1 . .
H H2 0.233 0.8766 0.8894 0.02 Uiso calc U . R 1 . .
C C6 0.37388(7) 0.39779(9) 0.85203(6) 0.01156(14) Uani d . . . 1 . .
O O3 0.08470(7) 0.08102(9) 0.85330(7) 0.02876(18) Uani d . . . 1 . .
C C3 0.36613(8) 0.78244(9) 0.89508(7) 0.01625(16) Uani d . . . 1 . .
H H3 0.4096 0.8631 0.9096 0.02 Uiso calc U . R 1 . .
N N2 0.29694(6) 0.29977(8) 0.83062(6) 0.01268(13) Uani d . . . 1 . .
O O2 -0.01515(7) 0.47439(10) 0.87241(8) 0.0322(2) Uani d . . . 1 . .
H H2A 0.6263(17) -0.120(2) 0.9095(16) 0.051(6) Uiso d . . . 1 . .
C C8 0.49945(7) 0.23007(9) 0.84572(6) 0.01214(14) Uani d . . . 1 . .
C C4 0.40558(8) 0.65473(9) 0.88465(7) 0.01391(15) Uani d . . . 1 . .
H H4 0.476 0.6472 0.8909 0.017 Uiso calc U . R 1 . .
O O4 0.03563(7) 0.34708(9) 0.61929(7) 0.02550(17) Uani d . . . 1 . .
C C12 0.67626(8) 0.29888(10) 0.85764(7) 0.01543(15) Uani d . . . 1 . .
H H12 0.6493 0.3908 0.8424 0.019 Uiso calc U . R 1 . .
C C9 0.41562(8) 0.13335(9) 0.81559(7) 0.01446(15) Uani d . . . 1 . .
H H9 0.4259 0.0415 0.7989 0.017 Uiso calc U . R 1 . .
C C11 0.60859(7) 0.19410(9) 0.86085(7) 0.01277(14) Uani d . . . 1 . .
C C5 0.34061(7) 0.53789(9) 0.86497(6) 0.01188(14) Uani d . . . 1 . .
C C13 0.78102(8) 0.27325(11) 0.87583(8) 0.01837(17) Uani d . . . 1 . .
H H13 0.8252 0.3468 0.8743 0.022 Uiso calc U . R 1 . .
C C14 0.82084(8) 0.13868(11) 0.89635(8) 0.01809(17) Uani d . . . 1 . .
H H14 0.8922 0.1197 0.9078 0.022 Uiso calc U . R 1 . .
C C10 0.31799(8) 0.17140(9) 0.81011(7) 0.01496(15) Uani d . . . 1 . .
H H10 0.263 0.1033 0.7909 0.018 Uiso calc U . R 1 . .
C C7 0.47463(7) 0.36592(9) 0.86129(7) 0.01249(14) Uani d . . . 1 . .
H H7 0.5273 0.4367 0.8783 0.015 Uiso calc U . R 1 . .
C C18 0.11703(8) 0.18870(11) 0.84946(8) 0.01834(17) Uani d . . . 1 . .
C C17 0.05532(8) 0.43088(11) 0.86229(8) 0.01990(18) Uani d . . . 1 . .
C C16 0.65151(8) 0.05907(9) 0.88411(7) 0.01459(15) Uani d . . . 1 . .
C C15 0.75633(8) 0.03214(10) 0.90009(7) 0.01699(16) Uani d . . . 1 . .
H H15 0.7836 -0.0597 0.9136 0.02 Uiso calc U . R 1 . .
C C19 0.08541(8) 0.35815(10) 0.70633(8) 0.01733(17) Uani d . . . 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 Mn1 . 2.5510(2) ?
N1 C1 . 1.3446(12) ?
N1 C5 . 1.3566(12) ?
N1 Mn1 . 2.0411(8) ?
O1 C16 . 1.3678(12) ?
O1 H2A . 0.85(2) ?
C1 C2 . 1.3855(14) ?
C1 H1 . 0.95 ?
Mn1 C18 . 1.8019(10) ?
Mn1 C19 . 1.8026(11) ?
Mn1 C17 . 1.8189(11) ?
Mn1 N2 . 2.0278(8) ?
C2 C3 . 1.3871(14) ?
C2 H2 . 0.95 ?
C6 N2 . 1.3566(11) ?
C6 C7 . 1.3873(12) ?
C6 C5 . 1.4729(12) ?
O3 C18 . 1.1467(13) ?
C3 C4 . 1.3896(13) ?
C3 H3 . 0.95 ?
N2 C10 . 1.3417(12) ?
O2 C17 . 1.1450(13) ?
C8 C9 . 1.4007(13) ?
C8 C7 . 1.4041(12) ?
C8 C11 . 1.4794(13) ?
C4 C5 . 1.3929(12) ?
C4 H4 . 0.95 ?
O4 C19 . 1.1427(13) ?
C12 C13 . 1.3853(14) ?
C12 C11 . 1.4027(13) ?
C12 H12 . 0.95 ?
C9 C10 . 1.3816(13) ?
C9 H9 . 0.95 ?
C11 C16 . 1.4102(13) ?
C13 C14 . 1.3913(15) ?
C13 H13 . 0.95 ?
C14 C15 . 1.3878(14) ?
C14 H14 . 0.95 ?
C10 H10 . 0.95 ?
C7 H7 . 0.95 ?
C16 C15 . 1.3984(13) ?
C15 H15 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C5 . . 118.43(8) ?
C1 N1 Mn1 . . 125.93(7) ?
C5 N1 Mn1 . . 115.32(6) ?
C16 O1 H2A . . 110.2(14) ?
N1 C1 C2 . . 122.78(9) ?
N1 C1 H1 . . 118.6 ?
C2 C1 H1 . . 118.6 ?
C18 Mn1 C19 . . 89.59(5) ?
C18 Mn1 C17 . . 88.75(5) ?
C19 Mn1 C17 . . 92.60(5) ?
C18 Mn1 N2 . . 96.88(4) ?
C19 Mn1 N2 . . 90.12(4) ?
C17 Mn1 N2 . . 173.77(4) ?
C18 Mn1 N1 . . 171.98(4) ?
C19 Mn1 N1 . . 97.22(4) ?
C17 Mn1 N1 . . 95.15(4) ?
N2 Mn1 N1 . . 78.94(3) ?
C18 Mn1 Br1 . . 87.34(3) ?
C19 Mn1 Br1 . . 175.60(3) ?
C17 Mn1 Br1 . . 90.49(4) ?
N2 Mn1 Br1 . . 87.11(2) ?
N1 Mn1 Br1 . . 85.62(2) ?
C1 C2 C3 . . 118.90(9) ?
C1 C2 H2 . . 120.6 ?
C3 C2 H2 . . 120.6 ?
N2 C6 C7 . . 121.93(8) ?
N2 C6 C5 . . 114.00(8) ?
C7 C6 C5 . . 124.06(8) ?
C2 C3 C4 . . 118.95(9) ?
C2 C3 H3 . . 120.5 ?
C4 C3 H3 . . 120.5 ?
C10 N2 C6 . . 117.61(8) ?
C10 N2 Mn1 . . 126.27(6) ?
C6 N2 Mn1 . . 115.92(6) ?
C9 C8 C7 . . 116.14(8) ?
C9 C8 C11 . . 123.03(8) ?
C7 C8 C11 . . 120.83(8) ?
C3 C4 C5 . . 119.21(9) ?
C3 C4 H4 . . 120.4 ?
C5 C4 H4 . . 120.4 ?
C13 C12 C11 . . 122.40(9) ?
C13 C12 H12 . . 118.8 ?
C11 C12 H12 . . 118.8 ?
C10 C9 C8 . . 120.08(8) ?
C10 C9 H9 . . 120.0 ?
C8 C9 H9 . . 120.0 ?
C12 C11 C16 . . 117.25(8) ?
C12 C11 C8 . . 119.49(8) ?
C16 C11 C8 . . 123.17(8) ?
N1 C5 C4 . . 121.73(8) ?
N1 C5 C6 . . 114.46(7) ?
C4 C5 C6 . . 123.81(8) ?
C12 C13 C14 . . 119.33(9) ?
C12 C13 H13 . . 120.3 ?
C14 C13 H13 . . 120.3 ?
C15 C14 C13 . . 119.97(9) ?
C15 C14 H14 . . 120.0 ?
C13 C14 H14 . . 120.0 ?
N2 C10 C9 . . 123.27(8) ?
N2 C10 H10 . . 118.4 ?
C9 C10 H10 . . 118.4 ?
C6 C7 C8 . . 120.64(8) ?
C6 C7 H7 . . 119.7 ?
C8 C7 H7 . . 119.7 ?
O3 C18 Mn1 . . 178.62(10) ?
O2 C17 Mn1 . . 178.88(11) ?
O1 C16 C15 . . 119.94(8) ?
O1 C16 C11 . . 119.47(8) ?
C15 C16 C11 . . 120.53(9) ?
C14 C15 C16 . . 120.47(9) ?
C14 C15 H15 . . 119.8 ?
C16 C15 H15 . . 119.8 ?
O4 C19 Mn1 . . 175.08(9) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C1 C2 . . . . -0.83(14) ?
Mn1 N1 C1 C2 . . . . 172.31(7) ?
N1 C1 C2 C3 . . . . -0.19(15) ?
C1 C2 C3 C4 . . . . 1.13(14) ?
C7 C6 N2 C10 . . . . -5.38(13) ?
C5 C6 N2 C10 . . . . 175.10(8) ?
C7 C6 N2 Mn1 . . . . 169.93(7) ?
C5 C6 N2 Mn1 . . . . -9.59(9) ?
C2 C3 C4 C5 . . . . -1.05(14) ?
C7 C8 C9 C10 . . . . -4.73(13) ?
C11 C8 C9 C10 . . . . 175.26(8) ?
C13 C12 C11 C16 . . . . 0.29(14) ?
C13 C12 C11 C8 . . . . 176.99(9) ?
C9 C8 C11 C12 . . . . 159.20(9) ?
C7 C8 C11 C12 . . . . -20.82(13) ?
C9 C8 C11 C16 . . . . -24.31(14) ?
C7 C8 C11 C16 . . . . 155.68(9) ?
C1 N1 C5 C4 . . . . 0.90(13) ?
Mn1 N1 C5 C4 . . . . -172.95(7) ?
C1 N1 C5 C6 . . . . -178.78(8) ?
Mn1 N1 C5 C6 . . . . 7.36(9) ?
C3 C4 C5 N1 . . . . 0.03(13) ?
C3 C4 C5 C6 . . . . 179.68(8) ?
N2 C6 C5 N1 . . . . 1.39(11) ?
C7 C6 C5 N1 . . . . -178.12(8) ?
N2 C6 C5 C4 . . . . -178.29(8) ?
C7 C6 C5 C4 . . . . 2.20(14) ?
C11 C12 C13 C14 . . . . 1.14(15) ?
C12 C13 C14 C15 . . . . -1.05(15) ?
C6 N2 C10 C9 . . . . 3.83(14) ?
Mn1 N2 C10 C9 . . . . -170.93(7) ?
C8 C9 C10 N2 . . . . 1.30(15) ?
N2 C6 C7 C8 . . . . 1.85(13) ?
C5 C6 C7 C8 . . . . -178.68(8) ?
C9 C8 C7 C6 . . . . 3.23(13) ?
C11 C8 C7 C6 . . . . -176.76(8) ?
C12 C11 C16 O1 . . . . 175.49(9) ?
C8 C11 C16 O1 . . . . -1.08(14) ?
C12 C11 C16 C15 . . . . -1.82(13) ?
C8 C11 C16 C15 . . . . -178.39(8) ?
C13 C14 C15 C16 . . . . -0.47(15) ?
O1 C16 C15 C14 . . . . -175.36(9) ?
C11 C16 C15 C14 . . . . 1.94(14) ?




_publcif_funding_html            
;
;
####################################################################### 
# 
# 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_I_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1902804'
loop_
_audit_author_name
_audit_author_address
'Philip Jeffrey'
;Princeton University
United States of America
;
_audit_update_record             
;
2019-03-12 deposited with the CCDC.	2019-07-23 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            5-OH
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H12 Br Mn N2 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         467.16

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   26.7689(16)
_cell_length_b                   8.7144(6)
_cell_length_c                   18.1821(11)
_cell_angle_alpha                90
_cell_angle_beta                 120.8861(18)
_cell_angle_gamma                90
_cell_volume                     3639.9(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9518
_cell_measurement_theta_min      2.6107
_cell_measurement_theta_max      37.8296
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       'rectangular prism'
_exptl_crystal_colour            'translucent intense orange'
_exptl_crystal_size_max          0.362
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.162
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1856

_exptl_absorpt_coefficient_mu    2.948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.40
_exptl_absorpt_correction_T_max  0.65

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            98623
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         36.32
_diffrn_reflns_theta_full        36.32
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30

_refine_special_details          
;
;

_reflns_number_total             8837
_reflns_number_gt                7968
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0225
_refine_ls_wR_factor_gt          0.0569
_refine_ls_wR_factor_ref         0.0587
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_number_reflns         8837
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0285P)²+2.9554P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.912
_refine_diff_density_min         -0.362
_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 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'

_computing_data_collection       'Bruker Instrument Service v4.2.4'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.30966(2) 0.42990(2) 0.78760(2) 0.01316(2) Uani d . . . 1 . .
Mn Mn1 0.40704(2) 0.51360(2) 0.80920(2) 0.00923(3) Uani d . . . 1 . .
O O1 0.26540(3) 0.17026(9) 0.41210(5) 0.01672(13) Uani d . . . 1 . .
H H1A 0.2473(8) 0.135(2) 0.3652(12) 0.029(4) Uiso d . . . 1 . .
N N1 0.36958(3) 0.72048(9) 0.75551(5) 0.01116(12) Uani d . . . 1 . .
C C1 0.36662(4) 0.84478(11) 0.79715(6) 0.01476(15) Uani d . . . 1 . .
H H1 0.3834 0.8391 0.8575 0.018 Uiso calc U . R 1 . .
O O2 0.44409(4) 0.59604(10) 0.98788(5) 0.02131(15) Uani d . . . 1 . .
N N2 0.37528(3) 0.46944(8) 0.68209(5) 0.00963(11) Uani d . . . 1 . .
C C2 0.34019(4) 0.98077(11) 0.75579(6) 0.01550(15) Uani d . . . 1 . .
H H2 0.3385 1.0657 0.7872 0.019 Uiso calc U . R 1 . .
O O3 0.45289(4) 0.20132(9) 0.87054(5) 0.02122(14) Uani d . . . 1 . .
C C3 0.31631(4) 0.99094(10) 0.66787(6) 0.01461(15) Uani d . . . 1 . .
H H3 0.2982 1.083 0.6381 0.018 Uiso calc U . R 1 . .
O O4 0.52391(4) 0.60196(11) 0.84643(5) 0.02239(15) Uani d . . . 1 . .
C C4 0.31943(4) 0.86410(10) 0.62436(6) 0.01307(14) Uani d . . . 1 . .
H H4 0.3038 0.8686 0.5642 0.016 Uiso calc U . R 1 . .
C C5 0.34566(4) 0.73016(10) 0.66944(5) 0.01034(13) Uani d . . . 1 . .
C C6 0.34880(4) 0.58864(9) 0.62835(5) 0.00967(12) Uani d . . . 1 . .
C C7 0.32611(4) 0.57495(10) 0.54043(5) 0.01160(13) Uani d . . . 1 . .
H H7 0.3081 0.6606 0.5039 0.014 Uiso calc U . R 1 . .
C C8 0.32984(4) 0.43630(10) 0.50658(5) 0.01161(13) Uani d . . . 1 . .
H H8 0.3146 0.4261 0.4467 0.014 Uiso calc U . R 1 . .
C C9 0.35623(4) 0.31149(9) 0.56114(5) 0.01028(13) Uani d . . . 1 . .
C C10 0.37854(4) 0.33517(10) 0.64848(5) 0.01034(12) Uani d . . . 1 . .
H H10 0.3971 0.2515 0.6864 0.012 Uiso calc U . R 1 . .
C C11 0.36256(4) 0.15988(10) 0.53027(5) 0.01116(13) Uani d . . . 1 . .
C C12 0.41506(4) 0.07989(11) 0.57529(6) 0.01572(15) Uani d . . . 1 . .
H H12 0.4462 0.1236 0.626 0.019 Uiso calc U . R 1 . .
C C13 0.42289(5) -0.06208(12) 0.54780(7) 0.01968(18) Uani d . . . 1 . .
H H13 0.4592 -0.1138 0.5788 0.024 Uiso calc U . R 1 . .
C C14 0.37698(5) -0.12741(11) 0.47433(7) 0.01791(17) Uani d . . . 1 . .
H H14 0.3818 -0.2247 0.4552 0.021 Uiso calc U . R 1 . .
C C15 0.32408(5) -0.05141(10) 0.42877(6) 0.01493(15) Uani d . . . 1 . .
H H15 0.2927 -0.0976 0.3792 0.018 Uiso calc U . R 1 . .
C C16 0.31682(4) 0.09295(10) 0.45560(6) 0.01195(13) Uani d . . . 1 . .
C C17 0.42913(4) 0.56549(11) 0.91813(6) 0.01357(14) Uani d . . . 1 . .
C C18 0.43474(4) 0.32212(11) 0.84635(6) 0.01339(14) Uani d . . . 1 . .
C C19 0.47777(4) 0.56978(11) 0.82951(6) 0.01377(14) Uani d . . . 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 Mn1 . 2.5359(2) ?
Mn1 C19 . 1.8008(10) ?
Mn1 C17 . 1.8096(9) ?
Mn1 C18 . 1.8100(10) ?
Mn1 N2 . 2.0481(7) ?
Mn1 N1 . 2.0503(8) ?
O1 C16 . 1.3625(12) ?
O1 H1A . 0.796(18) ?
N1 C1 . 1.3471(11) ?
N1 C5 . 1.3554(11) ?
C1 C2 . 1.3872(14) ?
C1 H1 . 0.95 ?
O2 C17 . 1.1480(11) ?
N2 C10 . 1.3435(11) ?
N2 C6 . 1.3510(11) ?
C2 C3 . 1.3865(14) ?
C2 H2 . 0.95 ?
O3 C18 . 1.1482(12) ?
C3 C4 . 1.3866(13) ?
C3 H3 . 0.95 ?
O4 C19 . 1.1440(12) ?
C4 C5 . 1.3915(12) ?
C4 H4 . 0.95 ?
C5 C6 . 1.4665(12) ?
C6 C7 . 1.3934(12) ?
C7 C8 . 1.3827(12) ?
C7 H7 . 0.95 ?
C8 C9 . 1.3952(12) ?
C8 H8 . 0.95 ?
C9 C10 . 1.3954(12) ?
C9 C11 . 1.4788(12) ?
C10 H10 . 0.95 ?
C11 C12 . 1.3964(13) ?
C11 C16 . 1.4056(12) ?
C12 C13 . 1.3900(14) ?
C12 H12 . 0.95 ?
C13 C14 . 1.3906(16) ?
C13 H13 . 0.95 ?
C14 C15 . 1.3876(15) ?
C14 H14 . 0.95 ?
C15 C16 . 1.3985(12) ?
C15 H15 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C19 Mn1 C17 . . 89.38(4) ?
C19 Mn1 C18 . . 89.31(4) ?
C17 Mn1 C18 . . 88.90(4) ?
C19 Mn1 N2 . . 93.80(4) ?
C17 Mn1 N2 . . 174.35(4) ?
C18 Mn1 N2 . . 95.81(4) ?
C19 Mn1 N1 . . 93.69(4) ?
C17 Mn1 N1 . . 96.12(4) ?
C18 Mn1 N1 . . 174.18(4) ?
N2 Mn1 N1 . . 79.03(3) ?
C19 Mn1 Br1 . . 177.37(3) ?
C17 Mn1 Br1 . . 88.49(3) ?
C18 Mn1 Br1 . . 89.09(3) ?
N2 Mn1 Br1 . . 88.45(2) ?
N1 Mn1 Br1 . . 88.08(2) ?
C16 O1 H1A . . 107.9(13) ?
C1 N1 C5 . . 118.01(8) ?
C1 N1 Mn1 . . 126.51(6) ?
C5 N1 Mn1 . . 115.48(6) ?
N1 C1 C2 . . 122.89(8) ?
N1 C1 H1 . . 118.6 ?
C2 C1 H1 . . 118.6 ?
C10 N2 C6 . . 118.24(7) ?
C10 N2 Mn1 . . 126.20(6) ?
C6 N2 Mn1 . . 115.56(6) ?
C3 C2 C1 . . 118.99(8) ?
C3 C2 H2 . . 120.5 ?
C1 C2 H2 . . 120.5 ?
C2 C3 C4 . . 118.67(9) ?
C2 C3 H3 . . 120.7 ?
C4 C3 H3 . . 120.7 ?
C3 C4 C5 . . 119.51(8) ?
C3 C4 H4 . . 120.2 ?
C5 C4 H4 . . 120.2 ?
N1 C5 C4 . . 121.92(8) ?
N1 C5 C6 . . 114.78(7) ?
C4 C5 C6 . . 123.29(8) ?
N2 C6 C7 . . 121.45(8) ?
N2 C6 C5 . . 115.10(7) ?
C7 C6 C5 . . 123.45(8) ?
C8 C7 C6 . . 119.80(8) ?
C8 C7 H7 . . 120.1 ?
C6 C7 H7 . . 120.1 ?
C7 C8 C9 . . 119.38(8) ?
C7 C8 H8 . . 120.3 ?
C9 C8 H8 . . 120.3 ?
C8 C9 C10 . . 117.29(8) ?
C8 C9 C11 . . 122.78(7) ?
C10 C9 C11 . . 119.91(7) ?
N2 C10 C9 . . 123.82(8) ?
N2 C10 H10 . . 118.1 ?
C9 C10 H10 . . 118.1 ?
C12 C11 C16 . . 118.33(8) ?
C12 C11 C9 . . 120.03(8) ?
C16 C11 C9 . . 121.64(8) ?
C13 C12 C11 . . 121.72(9) ?
C13 C12 H12 . . 119.1 ?
C11 C12 H12 . . 119.1 ?
C12 C13 C14 . . 119.19(10) ?
C12 C13 H13 . . 120.4 ?
C14 C13 H13 . . 120.4 ?
C15 C14 C13 . . 120.40(9) ?
C15 C14 H14 . . 119.8 ?
C13 C14 H14 . . 119.8 ?
C14 C15 C16 . . 120.20(9) ?
C14 C15 H15 . . 119.9 ?
C16 C15 H15 . . 119.9 ?
O1 C16 C15 . . 121.48(8) ?
O1 C16 C11 . . 118.37(8) ?
C15 C16 C11 . . 120.13(9) ?
O2 C17 Mn1 . . 178.50(9) ?
O3 C18 Mn1 . . 179.25(11) ?
O4 C19 Mn1 . . 176.50(9) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C1 C2 . . . . 0.14(14) ?
Mn1 N1 C1 C2 . . . . -179.76(7) ?
N1 C1 C2 C3 . . . . -0.84(15) ?
C1 C2 C3 C4 . . . . 0.38(14) ?
C2 C3 C4 C5 . . . . 0.72(14) ?
C1 N1 C5 C4 . . . . 1.02(13) ?
Mn1 N1 C5 C4 . . . . -179.07(7) ?
C1 N1 C5 C6 . . . . -177.94(8) ?
Mn1 N1 C5 C6 . . . . 1.97(9) ?
C3 C4 C5 N1 . . . . -1.46(14) ?
C3 C4 C5 C6 . . . . 177.41(8) ?
C10 N2 C6 C7 . . . . -1.00(12) ?
Mn1 N2 C6 C7 . . . . 178.93(7) ?
C10 N2 C6 C5 . . . . 178.57(7) ?
Mn1 N2 C6 C5 . . . . -1.51(9) ?
N1 C5 C6 N2 . . . . -0.31(11) ?
C4 C5 C6 N2 . . . . -179.25(8) ?
N1 C5 C6 C7 . . . . 179.25(8) ?
C4 C5 C6 C7 . . . . 0.31(14) ?
N2 C6 C7 C8 . . . . 0.86(13) ?
C5 C6 C7 C8 . . . . -178.67(8) ?
C6 C7 C8 C9 . . . . 0.19(13) ?
C7 C8 C9 C10 . . . . -1.02(13) ?
C7 C8 C9 C11 . . . . -179.31(8) ?
C6 N2 C10 C9 . . . . 0.10(13) ?
Mn1 N2 C10 C9 . . . . -179.82(6) ?
C8 C9 C10 N2 . . . . 0.91(13) ?
C11 C9 C10 N2 . . . . 179.26(8) ?
C8 C9 C11 C12 . . . . 136.14(9) ?
C10 C9 C11 C12 . . . . -42.11(12) ?
C8 C9 C11 C16 . . . . -43.49(12) ?
C10 C9 C11 C16 . . . . 138.25(9) ?
C16 C11 C12 C13 . . . . 0.35(14) ?
C9 C11 C12 C13 . . . . -179.30(9) ?
C11 C12 C13 C14 . . . . -1.06(16) ?
C12 C13 C14 C15 . . . . 0.34(16) ?
C13 C14 C15 C16 . . . . 1.09(15) ?
C14 C15 C16 O1 . . . . 179.96(9) ?
C14 C15 C16 C11 . . . . -1.80(14) ?
C12 C11 C16 O1 . . . . 179.38(8) ?
C9 C11 C16 O1 . . . . -0.98(12) ?
C12 C11 C16 C15 . . . . 1.08(13) ?
C9 C11 C16 C15 . . . . -179.28(8) ?




_publcif_funding_html            
;
;
