# 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_12jana_0m
_database_code_depnum_ccdc_archive 'CCDC 1878549'
loop_
_audit_author_name
_audit_author_address
'Sujan Shee'
;IIT Kanpur
India
;
_audit_update_record             
;
2018-11-12 deposited with the CCDC.	2019-03-20 downloaded from the CCDC.
;
_audit_creation_date             2018-11-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H13 Br Mn N3 O3'
_chemical_formula_sum            'C17 H13 Br Mn N3 O3'
_chemical_formula_weight         442.15
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.740(5)
_cell_length_b                   10.095(5)
_cell_length_c                   12.203(5)
_cell_angle_alpha                108.914(5)
_cell_angle_beta                 102.309(5)
_cell_angle_gamma                100.172(5)
_cell_volume                     849.6(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8081
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.29
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.150
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5352
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0971 before and 0.0370 after correction.
The Ratio of minimum to maximum transmission is 0.7177.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.728
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13352
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.325
_diffrn_reflns_theta_min         2.794
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3798
_reflns_number_total             4206
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0212
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0210P)²+0.4900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0518
_refine_ls_wR_factor_ref         0.0541
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 N006(H006)
2.b Secondary CH2 refined with riding coordinates:
 C023(H02A,H02B)
2.c Aromatic/amide H refined with riding coordinates:
 N007(H007), C010(H010), C011(H011), C012(H012), C013(H013), C014(H014),
 C016(H016), C019(H019), C020(H020), C021(H021)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br01 Br 0.70912(2) 0.50508(2) 0.88446(2) 0.01528(5) Uani 1 1 d . . . . .
Mn02 Mn 0.71892(3) 0.28133(3) 0.71528(2) 0.01093(6) Uani 1 1 d . . . . .
O003 O 0.40449(17) 0.11351(14) 0.75834(12) 0.0208(3) Uani 1 1 d . . . . .
O004 O 0.72609(19) 0.01497(14) 0.52684(11) 0.0228(3) Uani 1 1 d . . . . .
O005 O 0.45705(18) 0.33562(15) 0.53107(12) 0.0248(3) Uani 1 1 d . . . . .
N006 N 0.92069(19) 0.25623(15) 0.84962(12) 0.0127(3) Uani 1 1 d . . . . .
H006 H 0.949456 0.345335 0.921329 0.015 Uiso 1 1 calc R . . . .
N007 N 1.25988(19) 0.46548(16) 0.76478(13) 0.0169(3) Uani 1 1 d . . . . .
H007 H 1.370872 0.464384 0.793776 0.020 Uiso 1 1 calc R . . . .
N008 N 0.95525(19) 0.40419(15) 0.71212(12) 0.0130(3) Uani 1 1 d . . . . .
C009 C 1.0135(2) 0.52028(18) 0.67847(14) 0.0142(3) Uani 1 1 d . . . . .
C010 C 1.2050(3) 0.7450(2) 0.63418(16) 0.0230(4) Uani 1 1 d . . . . .
H010 H 1.266669 0.821539 0.618611 0.028 Uiso 1 1 calc R . . . .
C011 C 0.9136(2) 0.59477(18) 0.62284(15) 0.0167(3) Uani 1 1 d . . . . .
H011 H 0.786071 0.570041 0.601070 0.020 Uiso 1 1 calc R . . . .
C012 C 0.7239(2) -0.0814(2) 0.96070(17) 0.0208(4) Uani 1 1 d . . . . .
H012 H 0.675843 -0.155601 0.983938 0.025 Uiso 1 1 calc R . . . .
C013 C 0.7894(2) -0.11264(19) 0.86080(17) 0.0200(4) Uani 1 1 d . . . . .
H013 H 0.788002 -0.207909 0.818206 0.024 Uiso 1 1 calc R . . . .
C014 C 0.8000(2) 0.17142(19) 0.99052(15) 0.0174(3) Uani 1 1 d . . . . .
H014 H 0.805066 0.267083 1.034717 0.021 Uiso 1 1 calc R . . . .
C015 C 0.5268(2) 0.17791(18) 0.74182(15) 0.0152(3) Uani 1 1 d . . . . .
C016 C 1.3050(3) 0.6716(2) 0.68878(16) 0.0211(4) Uani 1 1 d . . . . .
H016 H 1.432430 0.695907 0.709724 0.025 Uiso 1 1 calc R . . . .
C017 C 0.8622(2) 0.13889(18) 0.88895(15) 0.0135(3) Uani 1 1 d . . . . .
C018 C 0.7255(2) 0.12005(19) 0.60052(15) 0.0154(3) Uani 1 1 d . . . . .
C019 C 0.7302(3) 0.0611(2) 1.02604(16) 0.0207(4) Uani 1 1 d . . . . .
H019 H 0.687530 0.082687 1.093782 0.025 Uiso 1 1 calc R . . . .
C020 C 1.0126(3) 0.7075(2) 0.60132(16) 0.0220(4) Uani 1 1 d . . . . .
H020 H 0.950000 0.759505 0.564252 0.026 Uiso 1 1 calc R . . . .
C021 C 0.8572(2) -0.00342(19) 0.82365(16) 0.0171(3) Uani 1 1 d . . . . .
H021 H 0.898941 -0.025243 0.755541 0.021 Uiso 1 1 calc R . . . .
C022 C 1.2054(2) 0.55916(19) 0.71100(15) 0.0166(3) Uani 1 1 d . . . . .
C023 C 1.0920(2) 0.26036(19) 0.81302(15) 0.0152(3) Uani 1 1 d . . . . .
H02A H 1.084245 0.167741 0.752119 0.018 Uiso 1 1 calc R . . . .
H02B H 1.197047 0.283322 0.882151 0.018 Uiso 1 1 calc R . . . .
C024 C 1.1067(2) 0.37672(18) 0.76311(15) 0.0147(3) Uani 1 1 d . . . . .
C025 C 0.5607(2) 0.31742(19) 0.60282(16) 0.0161(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br01 Mn02 2.5444(9) . ?
Mn02 N006 2.1232(16) . ?
Mn02 N008 2.0360(17) . ?
Mn02 C015 1.812(2) . ?
Mn02 C018 1.7879(19) . ?
Mn02 C025 1.8113(18) . ?
O003 C015 1.144(2) . ?
O004 C018 1.148(2) . ?
O005 C025 1.141(2) . ?
N006 C017 1.453(2) . ?
N006 C023 1.485(2) . ?
N007 C022 1.388(2) . ?
N007 C024 1.346(2) . ?
N008 C009 1.396(2) . ?
N008 C024 1.324(2) . ?
C009 C011 1.392(2) . ?
C009 C022 1.400(2) . ?
C010 C016 1.376(3) . ?
C010 C020 1.404(3) . ?
C011 C020 1.387(3) . ?
C012 C013 1.383(3) . ?
C012 C019 1.386(3) . ?
C013 C021 1.385(3) . ?
C014 C017 1.386(2) . ?
C014 C019 1.385(3) . ?
C016 C022 1.391(3) . ?
C017 C021 1.388(2) . ?
C023 C024 1.487(2) . ?

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
N006 Mn02 Br01 86.01(5) . . ?
N008 Mn02 Br01 87.09(5) . . ?
N008 Mn02 N006 77.57(7) . . ?
C015 Mn02 Br01 88.46(6) . . ?
C015 Mn02 N006 94.65(8) . . ?
C015 Mn02 N008 171.29(7) . . ?
C018 Mn02 Br01 177.61(6) . . ?
C018 Mn02 N006 92.31(7) . . ?
C018 Mn02 N008 94.22(7) . . ?
C018 Mn02 C015 89.97(8) . . ?
C018 Mn02 C025 89.98(8) . . ?
C025 Mn02 Br01 91.82(6) . . ?
C025 Mn02 N006 175.01(7) . . ?
C025 Mn02 N008 97.84(8) . . ?
C025 Mn02 C015 89.78(9) . . ?
C017 N006 Mn02 116.02(10) . . ?
C017 N006 C023 115.86(13) . . ?
C023 N006 Mn02 108.54(10) . . ?
C024 N007 C022 107.27(15) . . ?
C009 N008 Mn02 139.45(11) . . ?
C024 N008 Mn02 114.60(12) . . ?
C024 N008 C009 105.79(14) . . ?
N008 C009 C022 108.52(15) . . ?
C011 C009 N008 130.71(16) . . ?
C011 C009 C022 120.77(16) . . ?
C016 C010 C020 121.86(17) . . ?
C020 C011 C009 117.04(17) . . ?
C013 C012 C019 119.74(17) . . ?
C012 C013 C021 120.61(17) . . ?
C019 C014 C017 119.87(16) . . ?
O003 C015 Mn02 179.32(16) . . ?
C010 C016 C022 116.50(17) . . ?
C014 C017 N006 117.93(15) . . ?
C014 C017 C021 120.29(16) . . ?
C021 C017 N006 121.66(15) . . ?
O004 C018 Mn02 178.50(16) . . ?
C014 C019 C012 120.07(17) . . ?
C011 C020 C010 121.53(18) . . ?
C013 C021 C017 119.41(17) . . ?
N007 C022 C009 105.80(15) . . ?
N007 C022 C016 131.91(17) . . ?
C016 C022 C009 122.29(17) . . ?
N006 C023 C024 104.63(13) . . ?
N007 C024 C023 128.07(15) . . ?
N008 C024 N007 112.61(16) . . ?
N008 C024 C023 119.29(15) . . ?
O005 C025 Mn02 177.64(16) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_27novf
_database_code_depnum_ccdc_archive 'CCDC 1883243'
loop_
_audit_author_name
_audit_author_address
'Sujan Shee'
;IIT Kanpur
India
;
_audit_update_record             
;
2018-12-05 deposited with the CCDC.	2019-03-20 downloaded from the CCDC.
;
_audit_creation_date             2018-12-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 Mn N4 O3, Br'
_chemical_formula_sum            'C20 H14 Br Mn N4 O3'
_chemical_formula_weight         493.19
_chemical_absolute_configuration unk
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   14.6520(13)
_cell_length_b                   29.737(3)
_cell_length_c                   10.2242(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4454.7(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9859
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.43
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    2.413
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5116
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1646 before and 0.0781 after correction.
The Ratio of minimum to maximum transmission is 0.6861.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1968
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1052
_diffrn_reflns_av_unetI/netI     0.0728
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            71212
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.261
_diffrn_reflns_theta_min         2.418
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.801
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                8222
_reflns_number_total             10992
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         1.367
_refine_diff_density_min         -0.857
_refine_diff_density_rms         0.105
_refine_ls_abs_structure_details 
;
 Flack x determined using 3046 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.048(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         10992
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0493
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0581P)²+3.7635P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1292
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 N011(H011), N3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C050(H05A,H05B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N012(H012), C1AA(H1AA), C2AA(H2AA), C17(H17), C027(H027), C030(H030),
 C031(H031), C036(H036), C038(H038), C15(H15), C14(H14), C16(H16), C049(H049),
 C6(H6), C8(H8), C7(H7), C060(H060), C0AA(H0AA), C4AA(H4AA), C3AA(H3AA),
 C5AA(H5AA)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 2.20066(7) -0.13607(3) 0.46987(9) 0.0206(2) Uani 1 1 d . . . . .
Mn04 Mn 1.68832(7) -0.14074(3) -0.16217(9) 0.0216(2) Uani 1 1 d . . . . .
N1 N 2.0704(4) -0.13432(18) 0.4014(5) 0.0209(11) Uani 1 1 d . . . . .
N4 N 2.1504(4) -0.10164(18) 0.6267(5) 0.0218(12) Uani 1 1 d . . . . .
N2 N 1.9654(4) -0.09984(19) 0.2816(5) 0.0255(13) Uani 1 1 d . . . . .
H2 H 1.940757 -0.080662 0.226346 0.031 Uiso 1 1 calc R . . . .
N011 N 1.6758(4) -0.07783(18) -0.0701(5) 0.0231(12) Uani 1 1 d . . . . .
H011 H 1.735131 -0.070233 -0.027031 0.028 Uiso 1 1 calc R . . . .
N012 N 1.4434(4) -0.11212(19) 0.0106(5) 0.0254(13) Uani 1 1 d . . . . .
H012 H 1.415355 -0.094237 0.066155 0.030 Uiso 1 1 calc R . . . .
O013 O 1.6912(4) -0.22842(16) -0.2991(5) 0.0355(12) Uani 1 1 d . . . . .
N014 N 1.5552(4) -0.14193(18) -0.1068(5) 0.0227(12) Uani 1 1 d . . . . .
N015 N 1.6432(4) -0.10393(17) -0.3186(5) 0.0204(11) Uani 1 1 d . . . . .
C017 C 1.4041(5) -0.1465(2) -0.0592(6) 0.0236(14) Uani 1 1 d . . . . .
O018 O 1.7501(4) -0.18861(19) 0.0753(6) 0.0442(14) Uani 1 1 d . . . . .
C019 C 1.4757(5) -0.1657(2) -0.1325(6) 0.0217(14) Uani 1 1 d . . . . .
C1AA C 2.0934(5) -0.0443(3) 0.8303(6) 0.0273(15) Uani 1 1 d . . . . .
H1AA H 2.075779 -0.025506 0.900955 0.033 Uiso 1 1 calc R . . . .
C2AA C 2.0942(5) -0.0904(2) 0.8436(7) 0.0310(17) Uani 1 1 d . . . . .
H2AA H 2.073686 -0.103729 0.922755 0.037 Uiso 1 1 calc R . . . .
C17 C 1.8297(5) -0.1467(2) 0.3515(7) 0.0303(17) Uani 1 1 d . . . . .
H17 H 1.784824 -0.131228 0.301595 0.036 Uiso 1 1 calc R . . . .
C5 C 2.1467(4) -0.0555(2) 0.6083(6) 0.0217(14) Uani 1 1 d . . . . .
N3 N 2.1963(4) -0.07186(18) 0.3851(5) 0.0230(12) Uani 1 1 d . . . . .
H3 H 2.258163 -0.064311 0.350303 0.028 Uiso 1 1 calc R . . . .
C027 C 1.4569(5) -0.2028(2) -0.2153(6) 0.0242(14) Uani 1 1 d . . . . .
H027 H 1.503428 -0.215735 -0.267969 0.029 Uiso 1 1 calc R . . . .
C4 C 2.1193(5) -0.0259(2) 0.7087(7) 0.0242(14) Uani 1 1 d . . . . .
C030 C 1.6340(5) 0.0330(2) -0.2386(8) 0.0321(16) Uani 1 1 d . . . . .
H030 H 1.633999 0.064255 -0.218891 0.038 Uiso 1 1 calc R . . . .
C031 C 1.3157(5) -0.1634(2) -0.0653(7) 0.0270(15) Uani 1 1 d . . . . .
H031 H 1.267617 -0.150087 -0.016443 0.032 Uiso 1 1 calc R . . . .
C032 C 1.6156(4) -0.0277(2) -0.3935(6) 0.0208(13) Uani 1 1 d . . . . .
C3 C 2.3168(5) -0.1310(2) 0.5288(6) 0.0242(14) Uani 1 1 d . . . . .
C11 C 2.0537(5) -0.1018(2) 0.3164(6) 0.0243(14) Uani 1 1 d . . . . .
C035 C 1.5319(5) -0.1106(2) -0.0206(6) 0.0242(15) Uani 1 1 d . . . . .
C036 C 1.6537(5) 0.0013(2) -0.1398(7) 0.0278(15) Uani 1 1 d . . . . .
H036 H 1.665745 0.011201 -0.053183 0.033 Uiso 1 1 calc R . . . .
C13 C 1.9872(5) -0.1557(2) 0.4249(6) 0.0245(14) Uani 1 1 d . . . . .
C038 C 1.3002(5) -0.1998(2) -0.1437(7) 0.0298(16) Uani 1 1 d . . . . .
H038 H 1.240376 -0.212108 -0.148270 0.036 Uiso 1 1 calc R . . . .
C10 C 2.1299(5) -0.0725(2) 0.2743(6) 0.0272(15) Uani 1 1 d . . . . .
H10A H 2.107568 -0.041764 0.255510 0.033 Uiso 1 1 calc R . . . .
H10B H 2.159013 -0.084689 0.194398 0.033 Uiso 1 1 calc R . . . .
C15 C 1.8728(5) -0.2043(2) 0.5063(7) 0.0284(15) Uani 1 1 d . . . . .
H15 H 1.854446 -0.228413 0.561316 0.034 Uiso 1 1 calc R . . . .
C041 C 1.6894(4) -0.1937(2) -0.2463(6) 0.0246(14) Uani 1 1 d . . . . .
C14 C 1.9631(5) -0.1912(2) 0.5039(6) 0.0246(15) Uani 1 1 d . . . . .
H14 H 2.007439 -0.206348 0.555474 0.030 Uiso 1 1 calc R . . . .
C043 C 1.6377(4) -0.0586(2) -0.2949(6) 0.0212(14) Uani 1 1 d . . . . .
C045 C 1.7248(5) -0.1694(2) -0.0147(7) 0.0278(15) Uani 1 1 d . . . . .
C12 C 1.9202(5) -0.1337(2) 0.3489(6) 0.0252(15) Uani 1 1 d . . . . .
C16 C 1.8073(5) -0.1823(2) 0.4280(8) 0.0331(17) Uani 1 1 d . . . . .
H16 H 1.745991 -0.192734 0.428807 0.040 Uiso 1 1 calc R . . . .
C048 C 1.6555(4) -0.0437(2) -0.1678(6) 0.0215(13) Uani 1 1 d . . . . .
C049 C 1.3696(5) -0.2194(2) -0.2171(7) 0.0285(16) Uani 1 1 d . . . . .
H049 H 1.356267 -0.244954 -0.269578 0.034 Uiso 1 1 calc R . . . .
C050 C 1.6028(5) -0.0802(2) 0.0326(7) 0.0287(16) Uani 1 1 d . . . . .
H05A H 1.627735 -0.092227 0.115424 0.034 Uiso 1 1 calc R . . . .
H05B H 1.576998 -0.049938 0.049407 0.034 Uiso 1 1 calc R . . . .
C051 C 2.1707(4) -0.0383(2) 0.4838(6) 0.0220(13) Uani 1 1 d . . . . .
C6 C 2.1188(5) 0.0212(2) 0.6811(7) 0.0278(16) Uani 1 1 d . . . . .
H6 H 2.100862 0.041938 0.746801 0.033 Uiso 1 1 calc R . . . .
C8 C 2.1687(5) 0.0064(2) 0.4599(7) 0.0267(15) Uani 1 1 d . . . . .
H8 H 2.183841 0.017506 0.375531 0.032 Uiso 1 1 calc R . . . .
C2 C 2.2463(5) -0.1619(2) 0.3254(7) 0.0261(15) Uani 1 1 d . . . . .
C7 C 2.1440(5) 0.0364(2) 0.5602(7) 0.0299(15) Uani 1 1 d . . . . .
H7 H 2.144866 0.067792 0.543632 0.036 Uiso 1 1 calc R . . . .
C058 C 1.8057(5) -0.1332(2) -0.2085(7) 0.0275(15) Uani 1 1 d . . . . .
C1 C 2.1921(4) -0.1907(2) 0.5426(6) 0.0231(14) Uani 1 1 d . . . . .
C060 C 1.6149(5) 0.0186(2) -0.3639(7) 0.0279(16) Uani 1 1 d . . . . .
H060 H 1.601186 0.039860 -0.430286 0.033 Uiso 1 1 calc R . . . .
O0AA O 1.8818(4) -0.12937(16) -0.2385(5) 0.0356(12) Uani 1 1 d . . . . .
O1AA O 2.3910(3) -0.12924(17) 0.5658(5) 0.0343(12) Uani 1 1 d . . . . .
O2AA O 2.2796(4) -0.17958(17) 0.2369(5) 0.0339(12) Uani 1 1 d . . . . .
O1 O 2.1863(3) -0.22644(15) 0.5849(5) 0.0281(11) Uani 1 1 d . . . . .
Br1 Br 2.38381(5) -0.04550(3) 0.23718(7) 0.0347(2) Uani 1 1 d . . . . .
Br2 Br 1.86046(5) -0.04099(3) 0.07405(7) 0.0366(2) Uani 1 1 d . . . . .
C0AA C 1.6208(5) -0.1185(2) -0.4366(6) 0.0251(14) Uani 1 1 d . . . . .
H0AA H 1.622209 -0.149957 -0.452708 0.030 Uiso 1 1 calc R . . . .
C4AA C 1.5941(4) -0.0447(2) -0.5182(6) 0.0255(14) Uani 1 1 d . . . . .
H4AA H 1.578775 -0.024796 -0.587440 0.031 Uiso 1 1 calc R . . . .
C3AA C 1.5952(5) -0.0898(2) -0.5391(7) 0.0275(15) Uani 1 1 d . . . . .
H3AA H 1.578937 -0.101817 -0.621990 0.033 Uiso 1 1 calc R . . . .
C5AA C 2.1248(5) -0.1176(2) 0.7421(6) 0.0271(15) Uani 1 1 d . . . . .
H5AA H 2.127569 -0.149140 0.756120 0.033 Uiso 1 1 calc R . . . .


_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 N1 2.033(5) . ?
Mn1 N4 2.040(6) . ?
Mn1 N3 2.098(5) . ?
Mn1 C3 1.811(7) . ?
Mn1 C2 1.794(7) . ?
Mn1 C1 1.792(7) . ?
Mn04 N011 2.102(5) . ?
Mn04 N014 2.031(6) . ?
Mn04 N015 2.048(5) . ?
Mn04 C041 1.796(7) . ?
Mn04 C045 1.812(8) . ?
Mn04 C058 1.799(8) . ?
N1 C11 1.324(8) . ?
N1 C13 1.396(8) . ?
N4 C5 1.387(8) . ?
N4 C5AA 1.326(8) . ?
N2 C11 1.343(8) . ?
N2 C12 1.387(9) . ?
N011 C048 1.456(8) . ?
N011 C050 1.501(8) . ?
N012 C017 1.374(8) . ?
N012 C035 1.335(9) . ?
O013 C041 1.164(8) . ?
N014 C019 1.388(8) . ?
N014 C035 1.326(8) . ?
N015 C043 1.373(8) . ?
N015 C0AA 1.323(8) . ?
C017 C019 1.410(9) . ?
C017 C031 1.391(10) . ?
O018 C045 1.145(9) . ?
C019 C027 1.418(9) . ?
C1AA C2AA 1.377(10) . ?
C1AA C4 1.411(9) . ?
C2AA C5AA 1.389(10) . ?
C17 C12 1.382(10) . ?
C17 C16 1.359(11) . ?
C5 C4 1.411(9) . ?
C5 C051 1.415(9) . ?
N3 C10 1.493(9) . ?
N3 C051 1.467(8) . ?
C027 C049 1.371(10) . ?
C4 C6 1.426(9) . ?
C030 C036 1.413(10) . ?
C030 C060 1.380(10) . ?
C031 C038 1.366(10) . ?
C032 C043 1.401(9) . ?
C032 C060 1.409(9) . ?
C032 C4AA 1.408(9) . ?
C3 O1AA 1.152(8) . ?
C11 C10 1.480(9) . ?
C035 C050 1.482(9) . ?
C036 C048 1.366(9) . ?
C13 C14 1.377(9) . ?
C13 C12 1.412(9) . ?
C038 C049 1.392(10) . ?
C15 C14 1.379(9) . ?
C15 C16 1.410(10) . ?
C043 C048 1.398(9) . ?
C051 C8 1.353(9) . ?
C6 C7 1.367(10) . ?
C8 C7 1.406(9) . ?
C2 O2AA 1.155(8) . ?
C058 O0AA 1.161(9) . ?
C1 O1 1.150(8) . ?
C0AA C3AA 1.401(9) . ?
C4AA C3AA 1.358(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Mn1 N4 85.4(2) . . ?
N1 Mn1 N3 78.8(2) . . ?
N4 Mn1 N3 81.8(2) . . ?
C3 Mn1 N1 173.7(3) . . ?
C3 Mn1 N4 92.0(3) . . ?
C3 Mn1 N3 95.2(3) . . ?
C2 Mn1 N1 94.4(3) . . ?
C2 Mn1 N4 175.2(3) . . ?
C2 Mn1 N3 93.5(3) . . ?
C2 Mn1 C3 87.7(3) . . ?
C1 Mn1 N1 95.8(3) . . ?
C1 Mn1 N4 96.0(3) . . ?
C1 Mn1 N3 174.2(3) . . ?
C1 Mn1 C3 90.2(3) . . ?
C1 Mn1 C2 88.8(3) . . ?
N014 Mn04 N011 78.9(2) . . ?
N014 Mn04 N015 85.2(2) . . ?
N015 Mn04 N011 81.1(2) . . ?
C041 Mn04 N011 175.1(3) . . ?
C041 Mn04 N014 97.3(3) . . ?
C041 Mn04 N015 95.6(3) . . ?
C041 Mn04 C045 89.0(3) . . ?
C041 Mn04 C058 88.6(3) . . ?
C045 Mn04 N011 94.1(3) . . ?
C045 Mn04 N014 92.5(3) . . ?
C045 Mn04 N015 175.1(3) . . ?
C058 Mn04 N011 95.2(3) . . ?
C058 Mn04 N014 173.8(3) . . ?
C058 Mn04 N015 92.1(3) . . ?
C058 Mn04 C045 89.7(3) . . ?
C11 N1 Mn1 114.8(4) . . ?
C11 N1 C13 106.5(5) . . ?
C13 N1 Mn1 138.5(4) . . ?
C5 N4 Mn1 113.8(4) . . ?
C5AA N4 Mn1 128.5(5) . . ?
C5AA N4 C5 117.6(6) . . ?
C11 N2 C12 107.3(6) . . ?
C048 N011 Mn04 109.4(4) . . ?
C048 N011 C050 111.5(5) . . ?
C050 N011 Mn04 109.5(4) . . ?
C035 N012 C017 107.9(6) . . ?
C019 N014 Mn04 139.7(4) . . ?
C035 N014 Mn04 114.9(5) . . ?
C035 N014 C019 105.4(6) . . ?
C043 N015 Mn04 114.0(4) . . ?
C0AA N015 Mn04 128.1(4) . . ?
C0AA N015 C043 117.9(5) . . ?
N012 C017 C019 105.3(6) . . ?
N012 C017 C031 133.1(6) . . ?
C031 C017 C019 121.5(6) . . ?
N014 C019 C017 108.6(6) . . ?
N014 C019 C027 132.2(6) . . ?
C017 C019 C027 119.2(6) . . ?
C2AA C1AA C4 118.2(6) . . ?
C1AA C2AA C5AA 120.5(7) . . ?
C16 C17 C12 117.5(7) . . ?
N4 C5 C4 122.0(6) . . ?
N4 C5 C051 117.9(6) . . ?
C4 C5 C051 120.0(6) . . ?
C10 N3 Mn1 108.8(4) . . ?
C051 N3 Mn1 110.0(4) . . ?
C051 N3 C10 111.4(5) . . ?
C049 C027 C019 118.0(6) . . ?
C1AA C4 C6 123.7(6) . . ?
C5 C4 C1AA 118.3(6) . . ?
C5 C4 C6 118.0(6) . . ?
C060 C030 C036 119.8(6) . . ?
C038 C031 C017 117.9(7) . . ?
C043 C032 C060 119.1(6) . . ?
C043 C032 C4AA 117.9(6) . . ?
C4AA C032 C060 123.0(6) . . ?
O1AA C3 Mn1 177.7(6) . . ?
N1 C11 N2 112.6(6) . . ?
N1 C11 C10 118.7(6) . . ?
N2 C11 C10 128.7(6) . . ?
N012 C035 C050 127.8(6) . . ?
N014 C035 N012 112.7(6) . . ?
N014 C035 C050 119.5(6) . . ?
C048 C036 C030 120.5(6) . . ?
N1 C13 C12 107.5(6) . . ?
C14 C13 N1 132.4(6) . . ?
C14 C13 C12 120.1(6) . . ?
C031 C038 C049 121.7(7) . . ?
C11 C10 N3 106.2(5) . . ?
C14 C15 C16 120.8(7) . . ?
O013 C041 Mn04 178.7(6) . . ?
C13 C14 C15 118.2(7) . . ?
N015 C043 C032 122.0(6) . . ?
N015 C043 C048 117.7(6) . . ?
C048 C043 C032 120.3(6) . . ?
O018 C045 Mn04 177.2(7) . . ?
N2 C12 C13 106.1(6) . . ?
C17 C12 N2 132.1(7) . . ?
C17 C12 C13 121.8(7) . . ?
C17 C16 C15 121.6(7) . . ?
C036 C048 N011 122.8(6) . . ?
C036 C048 C043 120.1(6) . . ?
C043 C048 N011 117.0(6) . . ?
C027 C049 C038 121.6(7) . . ?
C035 C050 N011 105.7(5) . . ?
C5 C051 N3 115.9(5) . . ?
C8 C051 C5 120.7(6) . . ?
C8 C051 N3 123.3(6) . . ?
C7 C6 C4 120.1(7) . . ?
C051 C8 C7 119.8(7) . . ?
O2AA C2 Mn1 176.0(6) . . ?
C6 C7 C8 121.3(6) . . ?
O0AA C058 Mn04 178.5(6) . . ?
O1 C1 Mn1 177.6(6) . . ?
C030 C060 C032 120.2(7) . . ?
N015 C0AA C3AA 123.3(6) . . ?
C3AA C4AA C032 119.6(6) . . ?
C4AA C3AA C0AA 119.1(6) . . ?
N4 C5AA C2AA 123.2(6) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.014 0.246 -0.131 185.5 56.4 ?
2 0.014 0.754 0.869 185.5 56.1 ?
3 0.486 0.254 0.131 185.5 55.6 ?
4 0.514 0.746 0.131 185.5 55.8 ?

_olex2_submission_special_instructions 'No special instructions were received'
