# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_j1
_database_code_depnum_ccdc_archive 'CCDC 1008412'
_audit_update_record             
;
2014-06-14 deposited with the CCDC.
2014-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H11 Br Mn N3 O3'
_chemical_formula_weight         392.10

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 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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   14.3770(9)
_cell_length_b                   10.7747(7)
_cell_length_c                   9.6613(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.8260(10)
_cell_angle_gamma                90
_cell_volume                     1459.27(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9953
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      32.56

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.785
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    3.655
_shelx_estimated_absorpt_T_min   0.309
_shelx_estimated_absorpt_T_max   0.811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3754
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX-II CCD'
_diffrn_measurement_method       'OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23397
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.384
_diffrn_reflns_theta_max         32.031
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5066
_reflns_number_gt                4427
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0447P)²+1.0927P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5066
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0838
_refine_ls_wR_factor_gt          0.0810
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.79843(2) -0.05411(2) 0.50328(3) 0.01312(7) Uani 1 1 d . . . . .
Br1 Br 0.65885(2) -0.02752(2) 0.29151(2) 0.01606(6) Uani 1 1 d . . . . .
N1 N 0.64825(12) -0.01496(14) 0.69394(17) 0.0150(3) Uani 1 1 d . . . . .
N2 N 0.71620(11) 0.14591(13) 0.62996(16) 0.0134(3) Uani 1 1 d . . . . .
N3 N 0.82528(11) 0.13476(14) 0.49115(16) 0.0139(3) Uani 1 1 d . . . . .
C1 C 0.71306(13) 0.01869(16) 0.61954(19) 0.0138(3) Uani 1 1 d . . . . .
C2 C 0.61067(14) 0.08885(17) 0.7488(2) 0.0174(3) Uani 1 1 d . . . . .
H2A H 0.5636 0.0880 0.8040 0.021 Uiso 1 1 calc R U . . .
C3 C 0.65324(13) 0.19042(17) 0.7096(2) 0.0166(3) Uani 1 1 d . . . . .
H3A H 0.6426 0.2745 0.7314 0.020 Uiso 1 1 calc R U . . .
C4 C 0.77756(13) 0.21027(16) 0.56137(19) 0.0135(3) Uani 1 1 d . . . . .
C5 C 0.78723(14) 0.33881(16) 0.5654(2) 0.0164(3) Uani 1 1 d . . . . .
H5A H 0.7513 0.3888 0.6156 0.020 Uiso 1 1 calc R U . . .
C6 C 0.85095(14) 0.39142(18) 0.4940(2) 0.0188(3) Uani 1 1 d . . . . .
H6A H 0.8599 0.4788 0.4948 0.023 Uiso 1 1 calc R U . . .
C7 C 0.90189(14) 0.31507(18) 0.4208(2) 0.0188(3) Uani 1 1 d . . . . .
H7A H 0.9460 0.3494 0.3713 0.023 Uiso 1 1 calc R U . . .
C8 C 0.88681(14) 0.18842(17) 0.4217(2) 0.0166(3) Uani 1 1 d . . . . .
H8A H 0.9213 0.1366 0.3712 0.020 Uiso 1 1 calc R U . . .
C9 C 0.61500(15) -0.14234(17) 0.7065(2) 0.0181(3) Uani 1 1 d . . . . .
H9A H 0.5901 -0.1497 0.7938 0.022 Uiso 1 1 calc R U . . .
H9B H 0.6693 -0.2004 0.7147 0.022 Uiso 1 1 calc R U . . .
C10 C 0.53698(15) -0.17773(19) 0.5783(2) 0.0214(4) Uani 1 1 d . . . . .
H10A H 0.5161 -0.2630 0.5895 0.032 Uiso 1 1 calc R U . . .
H10B H 0.5619 -0.1719 0.4920 0.032 Uiso 1 1 calc R U . . .
H10C H 0.4828 -0.1211 0.5709 0.032 Uiso 1 1 calc R U . . .
C11 C 0.89274(14) -0.07459(16) 0.6667(2) 0.0180(4) Uani 1 1 d . . . . .
O1 O 0.94521(12) -0.08887(15) 0.76260(18) 0.0257(3) Uani 1 1 d . . . . .
C12 C 0.76772(14) -0.21592(17) 0.5124(2) 0.0171(3) Uani 1 1 d . . . . .
O2 O 0.75252(12) -0.32033(13) 0.51610(16) 0.0240(3) Uani 1 1 d . . . . .
C13 C 0.87469(14) -0.09782(17) 0.3812(2) 0.0179(3) Uani 1 1 d . . . . .
O3 O 0.92189(12) -0.12794(15) 0.30604(18) 0.0274(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
Mn1 C12 1.8055(19) . ?
Mn1 C13 1.8407(19) . ?
Mn1 C11 1.852(2) . ?
Mn1 C1 1.9989(18) . ?
Mn1 N3 2.0795(15) . ?
Mn1 Br1 2.5441(4) . ?
N1 C1 1.347(2) . ?
N1 C2 1.397(2) . ?
N1 C9 1.467(2) . ?
N2 C1 1.374(2) . ?
N2 C4 1.399(2) . ?
N2 C3 1.396(2) . ?
N3 C4 1.341(2) . ?
N3 C8 1.353(2) . ?
C2 C3 1.349(3) . ?
C4 C5 1.392(2) . ?
C5 C6 1.385(3) . ?
C6 C7 1.394(3) . ?
C7 C8 1.382(3) . ?
C9 C10 1.524(3) . ?
C11 O1 1.068(3) . ?
C12 O2 1.148(2) . ?
C13 O3 1.146(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
C12 Mn1 C13 88.35(8) . . ?
C12 Mn1 C11 89.08(8) . . ?
C13 Mn1 C11 95.05(8) . . ?
C12 Mn1 C1 99.44(8) . . ?
C13 Mn1 C1 171.02(8) . . ?
C11 Mn1 C1 89.57(7) . . ?
C12 Mn1 N3 176.61(8) . . ?
C13 Mn1 N3 94.01(7) . . ?
C11 Mn1 N3 93.14(7) . . ?
C1 Mn1 N3 78.02(7) . . ?
C12 Mn1 Br1 89.44(6) . . ?
C13 Mn1 Br1 89.39(6) . . ?
C11 Mn1 Br1 175.28(6) . . ?
C1 Mn1 Br1 86.25(5) . . ?
N3 Mn1 Br1 88.14(4) . . ?
C1 N1 C2 111.03(16) . . ?
C1 N1 C9 124.95(16) . . ?
C2 N1 C9 123.83(16) . . ?
C1 N2 C4 118.26(15) . . ?
C1 N2 C3 111.60(15) . . ?
C4 N2 C3 130.13(15) . . ?
C4 N3 C8 117.12(15) . . ?
C4 N3 Mn1 116.29(12) . . ?
C8 N3 Mn1 126.59(12) . . ?
N1 C1 N2 104.17(15) . . ?
N1 C1 Mn1 141.09(13) . . ?
N2 C1 Mn1 114.73(13) . . ?
C3 C2 N1 107.74(16) . . ?
C2 C3 N2 105.45(15) . . ?
N3 C4 C5 123.97(17) . . ?
N3 C4 N2 112.70(15) . . ?
C5 C4 N2 123.33(16) . . ?
C6 C5 C4 117.79(17) . . ?
C5 C6 C7 119.44(17) . . ?
C8 C7 C6 118.60(18) . . ?
N3 C8 C7 123.08(17) . . ?
N1 C9 C10 111.18(15) . . ?
O1 C11 Mn1 177.64(18) . . ?
O2 C12 Mn1 176.42(18) . . ?
O3 C13 Mn1 178.37(17) . . ?

_refine_diff_density_max         0.857
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.103

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_j3
_database_code_depnum_ccdc_archive 'CCDC 1008413'
_audit_update_record             
;
2014-06-14 deposited with the CCDC.
2014-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 Mn N4 O3 S'
_chemical_formula_weight         370.27

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'
S S 0.1246 0.1234 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   16.1045(7)
_cell_length_b                   11.0234(5)
_cell_length_c                   8.8519(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.9660(10)
_cell_angle_gamma                90
_cell_volume                     1556.28(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9969
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      33.05

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    1.001
_shelx_estimated_absorpt_T_min   0.690
_shelx_estimated_absorpt_T_max   0.915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6168
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX-II CCD'
_diffrn_measurement_method       'OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25984
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.246
_diffrn_reflns_theta_max         31.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5165
_reflns_number_gt                4784
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0379P)²+0.5696P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5165
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0235
_refine_ls_wR_factor_ref         0.0668
_refine_ls_wR_factor_gt          0.0650
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.81533(2) -0.05942(2) 0.51687(2) 0.01241(5) Uani 1 1 d . . . . .
N1 N 0.66146(5) -0.01801(8) 0.70266(10) 0.01626(15) Uani 1 1 d . . . . .
N2 N 0.72682(5) 0.13694(7) 0.63389(9) 0.01453(14) Uani 1 1 d . . . . .
N3 N 0.83886(5) 0.12615(7) 0.50148(9) 0.01350(14) Uani 1 1 d . . . . .
C1 C 0.72844(6) 0.01237(9) 0.63561(10) 0.01416(16) Uani 1 1 d . . . . .
C2 C 0.61792(7) 0.08458(10) 0.74055(12) 0.01942(18) Uani 1 1 d . . . . .
H2A H 0.5685 0.0851 0.7879 0.023 Uiso 1 1 calc R U . . .
C3 C 0.65873(6) 0.18262(9) 0.69771(12) 0.01845(18) Uani 1 1 d . . . . .
H3A H 0.6442 0.2654 0.7086 0.022 Uiso 1 1 calc R U . . .
C4 C 0.78660(6) 0.19975(9) 0.56417(10) 0.01389(16) Uani 1 1 d . . . . .
C5 C 0.79092(6) 0.32566(9) 0.56106(12) 0.01824(18) Uani 1 1 d . . . . .
H5A H 0.7519 0.3742 0.6052 0.022 Uiso 1 1 calc R U . . .
C6 C 0.85408(7) 0.37797(9) 0.49145(12) 0.01988(19) Uani 1 1 d . . . . .
H6A H 0.8596 0.4637 0.4883 0.024 Uiso 1 1 calc R U . . .
C7 C 0.90925(6) 0.30377(10) 0.42624(12) 0.01915(18) Uani 1 1 d . . . . .
H7A H 0.9529 0.3379 0.3779 0.023 Uiso 1 1 calc R U . . .
C8 C 0.89941(6) 0.17937(9) 0.43305(11) 0.01672(17) Uani 1 1 d . . . . .
H8A H 0.9369 0.1290 0.3875 0.020 Uiso 1 1 calc R U . . .
C9 C 0.62795(7) -0.14087(9) 0.71574(13) 0.02087(19) Uani 1 1 d . . . . .
H9A H 0.6074 -0.1499 0.8155 0.025 Uiso 1 1 calc R U . . .
H9B H 0.6731 -0.2011 0.7107 0.025 Uiso 1 1 calc R U . . .
C10 C 0.55663(8) -0.16445(11) 0.58787(15) 0.0286(2) Uani 1 1 d . . . . .
H10A H 0.5348 -0.2466 0.5981 0.043 Uiso 1 1 calc R U . . .
H10B H 0.5773 -0.1567 0.4893 0.043 Uiso 1 1 calc R U . . .
H10C H 0.5118 -0.1053 0.5938 0.043 Uiso 1 1 calc R U . . .
C11 C 0.89188(6) -0.07645(9) 0.68433(11) 0.01600(17) Uani 1 1 d . . . . .
O1 O 0.94032(5) -0.08957(8) 0.79168(9) 0.02332(16) Uani 1 1 d . . . . .
C12 C 0.78891(6) -0.21861(10) 0.52811(11) 0.01788(17) Uani 1 1 d . . . . .
O2 O 0.77578(6) -0.32092(7) 0.53138(10) 0.02651(17) Uani 1 1 d . . . . .
C13 C 0.89052(6) -0.10030(9) 0.38754(11) 0.01713(17) Uani 1 1 d . . . . .
O3 O 0.93701(5) -0.12720(8) 0.30657(10) 0.02681(17) Uani 1 1 d . . . . .
N4 N 0.72452(5) -0.03524(8) 0.34044(10) 0.01691(15) Uani 1 1 d . . . . .
C14 C 0.66503(6) -0.02056(9) 0.25188(11) 0.01479(16) Uani 1 1 d . . . . .
S1 S 0.58334(2) 0.00565(2) 0.12472(3) 0.01999(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 C11 1.8016(10) . ?
Mn1 C12 1.8116(11) . ?
Mn1 C13 1.8342(10) . ?
Mn1 N4 2.0039(9) . ?
Mn1 C1 2.0241(9) . ?
Mn1 N3 2.0883(8) . ?
N1 C1 1.3436(12) . ?
N1 C2 1.3959(13) . ?
N1 C9 1.4683(13) . ?
N2 C1 1.3735(12) . ?
N2 C4 1.3971(12) . ?
N2 C3 1.3953(12) . ?
N3 C4 1.3431(12) . ?
N3 C8 1.3511(12) . ?
C2 C3 1.3464(14) . ?
C4 C5 1.3901(13) . ?
C5 C6 1.3859(14) . ?
C6 C7 1.3906(14) . ?
C7 C8 1.3827(14) . ?
C9 C10 1.5191(17) . ?
C11 O1 1.1520(13) . ?
C12 O2 1.1486(13) . ?
C13 O3 1.1450(13) . ?
N4 C14 1.1621(13) . ?
C14 S1 1.6342(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
C11 Mn1 C12 89.60(4) . . ?
C11 Mn1 C13 93.00(4) . . ?
C12 Mn1 C13 88.66(5) . . ?
C11 Mn1 N4 175.82(4) . . ?
C12 Mn1 N4 91.15(4) . . ?
C13 Mn1 N4 91.14(4) . . ?
C11 Mn1 C1 93.27(4) . . ?
C12 Mn1 C1 99.54(4) . . ?
C13 Mn1 C1 169.71(4) . . ?
N4 Mn1 C1 82.55(4) . . ?
C11 Mn1 N3 92.64(4) . . ?
C12 Mn1 N3 176.90(4) . . ?
C13 Mn1 N3 93.35(4) . . ?
N4 Mn1 N3 86.46(3) . . ?
C1 Mn1 N3 78.21(3) . . ?
C1 N1 C2 111.41(8) . . ?
C1 N1 C9 126.23(9) . . ?
C2 N1 C9 121.73(8) . . ?
C1 N2 C4 119.16(8) . . ?
C1 N2 C3 111.78(8) . . ?
C4 N2 C3 128.93(8) . . ?
C4 N3 C8 117.09(8) . . ?
C4 N3 Mn1 115.79(6) . . ?
C8 N3 Mn1 127.11(7) . . ?
N1 C1 N2 103.83(8) . . ?
N1 C1 Mn1 141.91(7) . . ?
N2 C1 Mn1 113.49(6) . . ?
C3 C2 N1 107.55(8) . . ?
C2 C3 N2 105.43(9) . . ?
N3 C4 C5 123.99(9) . . ?
N3 C4 N2 113.13(8) . . ?
C5 C4 N2 122.88(9) . . ?
C4 C5 C6 117.78(9) . . ?
C7 C6 C5 119.36(10) . . ?
C8 C7 C6 118.79(9) . . ?
N3 C8 C7 122.98(9) . . ?
N1 C9 C10 110.32(9) . . ?
O1 C11 Mn1 178.70(9) . . ?
O2 C12 Mn1 176.35(10) . . ?
O3 C13 Mn1 179.16(10) . . ?
C14 N4 Mn1 171.35(8) . . ?
N4 C14 S1 177.40(9) . . ?

_refine_diff_density_max         0.492
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.057

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_j2
_database_code_depnum_ccdc_archive 'CCDC 1008414'
_audit_update_record             
;
2014-06-14 deposited with the CCDC.
2014-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 Mn N4 O3'
_chemical_formula_weight         338.21

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   14.4018(15)
_cell_length_b                   10.6199(11)
_cell_length_c                   9.3898(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.9552(17)
_cell_angle_gamma                90
_cell_volume                     1410.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3241
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      25.39

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.954
_shelx_estimated_absorpt_T_min   0.832
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6084
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX-II CCD'
_diffrn_measurement_method       'OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22382
_diffrn_reflns_av_unetI/netI     0.0581
_diffrn_reflns_av_R_equivalents  0.0770
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.399
_diffrn_reflns_theta_max         30.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4299
_reflns_number_gt                3118
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0593P)²+0.1286P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4299
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1196
_refine_ls_wR_factor_gt          0.1063
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.29710(3) 0.94481(3) 0.00661(4) 0.01503(11) Uani 1 1 d . . . . .
N1 N 0.14298(14) 0.98369(19) 0.2010(2) 0.0167(4) Uani 1 1 d . . . . .
N2 N 0.21101(13) 1.14691(17) 0.1364(2) 0.0155(4) Uani 1 1 d . . . . .
N3 N 0.32479(14) 1.13644(18) -0.0029(2) 0.0156(4) Uani 1 1 d . . . . .
C1 C 0.20984(16) 1.0181(2) 0.1265(2) 0.0156(4) Uani 1 1 d . . . . .
C2 C 0.10271(17) 1.0884(2) 0.2561(3) 0.0196(5) Uani 1 1 d . . . . .
H2A H 0.0539 1.0871 0.3114 0.024 Uiso 1 1 calc R U . . .
C3 C 0.14572(16) 1.1909(2) 0.2164(2) 0.0193(5) Uani 1 1 d . . . . .
H3A H 0.1340 1.2761 0.2384 0.023 Uiso 1 1 calc R U . . .
C4 C 0.27375(16) 1.2129(2) 0.0670(2) 0.0151(4) Uani 1 1 d . . . . .
C5 C 0.28191(17) 1.3431(2) 0.0695(3) 0.0191(5) Uani 1 1 d . . . . .
H5A H 0.2436 1.3938 0.1184 0.023 Uiso 1 1 calc R U . . .
C6 C 0.34811(17) 1.3965(2) -0.0021(3) 0.0201(5) Uani 1 1 d . . . . .
H6A H 0.3563 1.4853 -0.0021 0.024 Uiso 1 1 calc R U . . .
C7 C 0.40247(17) 1.3192(2) -0.0739(3) 0.0207(5) Uani 1 1 d . . . . .
H7A H 0.4482 1.3541 -0.1233 0.025 Uiso 1 1 calc R U . . .
C8 C 0.38825(17) 1.1912(2) -0.0717(3) 0.0182(5) Uani 1 1 d . . . . .
H8A H 0.4251 1.1387 -0.1212 0.022 Uiso 1 1 calc R U . . .
C9 C 0.10856(18) 0.8539(2) 0.2102(3) 0.0209(5) Uani 1 1 d . . . . .
H9A H 0.0801 0.8451 0.2977 0.025 Uiso 1 1 calc R U . . .
H9B H 0.1623 0.7945 0.2191 0.025 Uiso 1 1 calc R U . . .
C10 C 0.03562(18) 0.8218(2) 0.0766(3) 0.0237(5) Uani 1 1 d . . . . .
H10A H 0.0135 0.7353 0.0844 0.035 Uiso 1 1 calc R U . . .
H10B H 0.0641 0.8296 -0.0098 0.035 Uiso 1 1 calc R U . . .
H10C H -0.0180 0.8799 0.0688 0.035 Uiso 1 1 calc R U . . .
C11 C 0.38789(17) 0.9237(2) 0.1690(3) 0.0178(5) Uani 1 1 d . . . . .
O1 O 0.44250(13) 0.90672(17) 0.27267(19) 0.0247(4) Uani 1 1 d . . . . .
C12 C 0.26561(17) 0.7815(2) 0.0163(3) 0.0189(5) Uani 1 1 d . . . . .
O2 O 0.24835(13) 0.67577(16) 0.0204(2) 0.0256(4) Uani 1 1 d . . . . .
C13 C 0.37432(17) 0.9031(2) -0.1200(3) 0.0195(5) Uani 1 1 d . . . . .
O3 O 0.42185(13) 0.87594(17) -0.1995(2) 0.0276(4) Uani 1 1 d . . . . .
C14 C 0.18928(17) 0.9703(2) -0.1599(3) 0.0167(4) Uani 1 1 d . . . . .
N4 N 0.12581(15) 0.9877(2) -0.2533(2) 0.0209(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 C12 1.799(2) . ?
Mn1 C11 1.824(3) . ?
Mn1 C13 1.830(2) . ?
Mn1 C1 1.998(2) . ?
Mn1 C14 2.002(3) . ?
Mn1 N3 2.0790(19) . ?
N1 C1 1.344(3) . ?
N1 C2 1.398(3) . ?
N1 C9 1.472(3) . ?
N2 C1 1.371(3) . ?
N2 C4 1.399(3) . ?
N2 C3 1.391(3) . ?
N3 C8 1.347(3) . ?
N3 C4 1.347(3) . ?
C2 C3 1.340(3) . ?
C4 C5 1.387(3) . ?
C5 C6 1.388(3) . ?
C6 C7 1.394(3) . ?
C7 C8 1.376(3) . ?
C9 C10 1.514(3) . ?
C11 O1 1.144(3) . ?
C12 O2 1.153(3) . ?
C13 O3 1.142(3) . ?
C14 N4 1.155(3) . ?

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
C12 Mn1 C11 89.25(10) . . ?
C12 Mn1 C13 89.43(11) . . ?
C11 Mn1 C13 94.92(11) . . ?
C12 Mn1 C1 98.93(10) . . ?
C11 Mn1 C1 90.26(10) . . ?
C13 Mn1 C1 170.23(10) . . ?
C12 Mn1 C14 90.25(10) . . ?
C11 Mn1 C14 174.93(10) . . ?
C13 Mn1 C14 90.12(10) . . ?
C1 Mn1 C14 84.83(9) . . ?
C12 Mn1 N3 176.33(9) . . ?
C11 Mn1 N3 92.47(9) . . ?
C13 Mn1 N3 93.66(9) . . ?
C1 Mn1 N3 77.82(8) . . ?
C14 Mn1 N3 87.75(8) . . ?
C1 N1 C2 111.4(2) . . ?
C1 N1 C9 124.6(2) . . ?
C2 N1 C9 123.7(2) . . ?
C1 N2 C4 118.00(19) . . ?
C1 N2 C3 111.74(19) . . ?
C4 N2 C3 130.26(19) . . ?
C8 N3 C4 117.12(19) . . ?
C8 N3 Mn1 126.60(16) . . ?
C4 N3 Mn1 116.28(15) . . ?
N1 C1 N2 103.72(19) . . ?
N1 C1 Mn1 141.00(18) . . ?
N2 C1 Mn1 115.19(16) . . ?
C3 C2 N1 107.3(2) . . ?
C2 C3 N2 105.9(2) . . ?
N3 C4 N2 112.66(19) . . ?
N3 C4 C5 123.9(2) . . ?
N2 C4 C5 123.5(2) . . ?
C6 C5 C4 117.6(2) . . ?
C5 C6 C7 119.6(2) . . ?
C8 C7 C6 118.4(2) . . ?
N3 C8 C7 123.4(2) . . ?
N1 C9 C10 110.51(19) . . ?
O1 C11 Mn1 177.1(2) . . ?
O2 C12 Mn1 177.4(2) . . ?
O3 C13 Mn1 179.2(2) . . ?
N4 C14 Mn1 177.8(2) . . ?

_refine_diff_density_max         0.727
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.094

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_j4
_database_code_depnum_ccdc_archive 'CCDC 1008415'
_audit_update_record             
;
2014-06-14 deposited with the CCDC.
2014-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 Br Mn N3 O3'
_chemical_formula_weight         442.15

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

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

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

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

_cell_length_a                   7.9754(9)
_cell_length_b                   8.7199(10)
_cell_length_c                   12.8037(15)
_cell_angle_alpha                83.171(2)
_cell_angle_beta                 84.768(2)
_cell_angle_gamma                79.192(2)
_cell_volume                     866.26(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6954
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      30.99

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    3.089
_shelx_estimated_absorpt_T_min   0.394
_shelx_estimated_absorpt_T_max   0.537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5549
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX-II CCD'
_diffrn_measurement_method       'OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13441
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.391
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5022
_reflns_number_gt                4374
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0338P)²+0.3932P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5022
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0746
_refine_ls_wR_factor_gt          0.0723
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.63027(3) 0.28403(3) 0.83953(2) 0.03031(7) Uani 1 1 d . . . . .
Br1 Br 0.75544(2) 0.39035(2) 0.66233(2) 0.03930(7) Uani 1 1 d . . . . .
N1 N 0.3455(2) 0.19190(18) 0.71883(13) 0.0338(3) Uani 1 1 d . . . . .
N2 N 0.5833(2) 0.02602(17) 0.73244(12) 0.0323(3) Uani 1 1 d . . . . .
N3 N 0.7978(2) 0.07527(19) 0.82273(12) 0.0343(3) Uani 1 1 d . . . . .
C1 C 0.4972(2) 0.1702(2) 0.76007(14) 0.0302(3) Uani 1 1 d . . . . .
C2 C 0.3332(2) 0.0689(2) 0.66087(15) 0.0352(4) Uani 1 1 d . . . . .
C3 C 0.2038(3) 0.0483(3) 0.60152(18) 0.0476(5) Uani 1 1 d . . . . .
H3A H 0.1021 0.1204 0.5974 0.057 Uiso 1 1 calc R U . . .
C4 C 0.2331(3) -0.0843(3) 0.5488(2) 0.0555(6) Uani 1 1 d . . . . .
H4A H 0.1495 -0.1021 0.5079 0.067 Uiso 1 1 calc R U . . .
C5 C 0.3847(4) -0.1914(3) 0.55563(19) 0.0537(6) Uani 1 1 d . . . . .
H5A H 0.4006 -0.2787 0.5182 0.064 Uiso 1 1 calc R U . . .
C6 C 0.5127(3) -0.1733(2) 0.61582(17) 0.0446(5) Uani 1 1 d . . . . .
H6A H 0.6130 -0.2471 0.6208 0.053 Uiso 1 1 calc R U . . .
C7 C 0.4853(3) -0.0394(2) 0.66894(15) 0.0345(4) Uani 1 1 d . . . . .
C8 C 0.7447(2) -0.0294(2) 0.77004(14) 0.0343(4) Uani 1 1 d . . . . .
C9 C 0.8383(3) -0.1782(3) 0.75828(19) 0.0496(5) Uani 1 1 d . . . . .
H9A H 0.7965 -0.2487 0.7229 0.060 Uiso 1 1 calc R U . . .
C10 C 0.9955(3) -0.2181(3) 0.8008(2) 0.0597(6) Uani 1 1 d . . . . .
H10A H 1.0613 -0.3170 0.7948 0.072 Uiso 1 1 calc R U . . .
C11 C 0.5351(3) 0.2104(3) 0.96472(18) 0.0484(5) Uani 1 1 d . . . . .
O1 O 0.4745(4) 0.1685(3) 1.04059(17) 0.0845(7) Uani 1 1 d . . . . .
C12 C 0.7798(3) 0.3757(3) 0.90178(17) 0.0435(4) Uani 1 1 d . . . . .
O2 O 0.8690(3) 0.4374(3) 0.93926(17) 0.0755(6) Uani 1 1 d . . . . .
C13 C 0.4817(3) 0.4669(2) 0.84152(17) 0.0422(4) Uani 1 1 d . . . . .
O3 O 0.3913(2) 0.5853(2) 0.84460(18) 0.0678(5) Uani 1 1 d . . . . .
C14 C 1.0547(3) -0.1108(3) 0.8521(2) 0.0541(6) Uani 1 1 d . . . . .
H14A H 1.1617 -0.1355 0.8795 0.065 Uiso 1 1 calc R U . . .
C15 C 0.9536(3) 0.0330(3) 0.86228(17) 0.0442(5) Uani 1 1 d . . . . .
H15A H 0.9935 0.1044 0.8978 0.053 Uiso 1 1 calc R U . . .
C16 C 0.2113(2) 0.3318(2) 0.72281(18) 0.0405(4) Uani 1 1 d . . . . .
H16A H 0.2185 0.3810 0.7859 0.049 Uiso 1 1 calc R U . . .
H16B H 0.1000 0.3009 0.7266 0.049 Uiso 1 1 calc R U . . .
C17 C 0.2280(4) 0.4479(3) 0.6276(2) 0.0596(6) Uani 1 1 d . . . . .
H17A H 0.1386 0.5379 0.6325 0.089 Uiso 1 1 calc R U . . .
H17B H 0.2188 0.4000 0.5651 0.089 Uiso 1 1 calc R U . . .
H17C H 0.3372 0.4801 0.6243 0.089 Uiso 1 1 calc R U . . .


_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 C13 1.801(2) . ?
Mn1 C11 1.810(2) . ?
Mn1 C12 1.838(2) . ?
Mn1 C1 1.9946(18) . ?
Mn1 N3 2.0673(16) . ?
Mn1 Br1 2.5372(4) . ?
N1 C1 1.336(2) . ?
N1 C2 1.398(2) . ?
N1 C16 1.467(2) . ?
N2 C1 1.384(2) . ?
N2 C8 1.395(2) . ?
N2 C7 1.411(2) . ?
N3 C8 1.345(3) . ?
N3 C15 1.354(3) . ?
C2 C3 1.385(3) . ?
C2 C7 1.394(3) . ?
C3 C4 1.379(3) . ?
C4 C5 1.385(4) . ?
C5 C6 1.376(3) . ?
C6 C7 1.392(3) . ?
C8 C9 1.388(3) . ?
C9 C10 1.380(3) . ?
C10 C14 1.378(4) . ?
C11 O1 1.098(3) . ?
C12 O2 1.137(3) . ?
C13 O3 1.146(3) . ?
C14 C15 1.371(3) . ?
C16 C17 1.502(3) . ?

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
C13 Mn1 C11 90.72(11) . . ?
C13 Mn1 C12 87.74(10) . . ?
C11 Mn1 C12 93.24(10) . . ?
C13 Mn1 C1 98.58(8) . . ?
C11 Mn1 C1 91.82(9) . . ?
C12 Mn1 C1 171.85(9) . . ?
C13 Mn1 N3 174.77(8) . . ?
C11 Mn1 N3 93.25(9) . . ?
C12 Mn1 N3 95.42(8) . . ?
C1 Mn1 N3 77.91(7) . . ?
C13 Mn1 Br1 88.12(7) . . ?
C11 Mn1 Br1 178.40(8) . . ?
C12 Mn1 Br1 87.81(7) . . ?
C1 Mn1 Br1 87.27(5) . . ?
N3 Mn1 Br1 87.85(4) . . ?
C1 N1 C2 111.52(15) . . ?
C1 N1 C16 126.11(15) . . ?
C2 N1 C16 122.12(16) . . ?
C1 N2 C8 117.52(15) . . ?
C1 N2 C7 110.96(15) . . ?
C8 N2 C7 131.52(16) . . ?
C8 N3 C15 117.31(17) . . ?
C8 N3 Mn1 116.73(12) . . ?
C15 N3 Mn1 125.93(14) . . ?
N1 C1 N2 105.55(15) . . ?
N1 C1 Mn1 139.40(13) . . ?
N2 C1 Mn1 114.98(12) . . ?
C3 C2 C7 122.22(19) . . ?
C3 C2 N1 130.53(19) . . ?
C7 C2 N1 107.23(16) . . ?
C4 C3 C2 116.8(2) . . ?
C3 C4 C5 121.3(2) . . ?
C6 C5 C4 122.4(2) . . ?
C5 C6 C7 117.0(2) . . ?
C6 C7 C2 120.39(19) . . ?
C6 C7 N2 134.89(19) . . ?
C2 C7 N2 104.67(15) . . ?
N3 C8 C9 123.29(19) . . ?
N3 C8 N2 112.64(15) . . ?
C9 C8 N2 124.03(19) . . ?
C10 C9 C8 117.8(2) . . ?
C14 C10 C9 119.8(2) . . ?
O1 C11 Mn1 178.5(3) . . ?
O2 C12 Mn1 177.6(2) . . ?
O3 C13 Mn1 177.5(2) . . ?
C15 C14 C10 119.0(2) . . ?
N3 C15 C14 122.7(2) . . ?
N1 C16 C17 111.47(18) . . ?

_refine_diff_density_max         0.848
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.058

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_j5
_database_code_depnum_ccdc_archive 'CCDC 1008416'
_audit_update_record             
;
2014-06-14 deposited with the CCDC.
2014-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H15 Cl2 Mn N4 O3'
_chemical_formula_weight         473.19

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'
Cl Cl 0.1484 0.1585 '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                   9.2310(9)
_cell_length_b                   9.9773(9)
_cell_length_c                   12.0386(11)
_cell_angle_alpha                85.5287(13)
_cell_angle_beta                 74.4239(13)
_cell_angle_gamma                69.7291(13)
_cell_volume                     1001.75(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7729
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      33.00

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.954
_shelx_estimated_absorpt_T_min   0.731
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6541
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX-II CCD'
_diffrn_measurement_method       'OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14745
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.176
_diffrn_reflns_theta_max         28.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5311
_reflns_number_gt                4627
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0359P)²+0.5830P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5311
_refine_ls_number_parameters     292
_refine_ls_number_restraints     75
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0779
_refine_ls_wR_factor_gt          0.0741
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.31635(3) 0.80563(2) 0.26993(2) 0.01303(7) Uani 1 1 d . . . . .
N1 N 0.19922(15) 0.54212(13) 0.28724(10) 0.0138(2) Uani 1 1 d . . . . .
N2 N 0.26732(14) 0.59043(13) 0.43451(10) 0.0128(2) Uani 1 1 d . . . . .
N3 N 0.33837(14) 0.78839(13) 0.43793(10) 0.0135(2) Uani 1 1 d . . . . .
C1 C 0.25193(17) 0.63514(15) 0.32514(12) 0.0135(3) Uani 1 1 d . . . . .
C2 C 0.18361(17) 0.43647(15) 0.36851(12) 0.0140(3) Uani 1 1 d . . . . .
C3 C 0.13300(18) 0.32118(16) 0.36453(13) 0.0166(3) Uani 1 1 d . . . . .
H3A H 0.1042 0.3018 0.2990 0.020 Uiso 1 1 calc R U . . .
C4 C 0.12669(18) 0.23575(15) 0.46153(13) 0.0177(3) Uani 1 1 d . . . . .
H4A H 0.0920 0.1563 0.4627 0.021 Uiso 1 1 calc R U . . .
C5 C 0.17015(18) 0.26440(15) 0.55701(13) 0.0172(3) Uani 1 1 d . . . . .
H5A H 0.1653 0.2032 0.6214 0.021 Uiso 1 1 calc R U . . .
C6 C 0.22048(18) 0.38016(15) 0.56096(13) 0.0158(3) Uani 1 1 d . . . . .
H6 H 0.2489(6) 0.3989(4) 0.6250(14) 0.019 Uiso 1 1 calc R U . . .
C7 C 0.22605(17) 0.46652(15) 0.46409(12) 0.0133(3) Uani 1 1 d . . . . .
C8 C 0.31110(17) 0.67528(15) 0.49778(12) 0.0133(3) Uani 1 1 d . . . . .
C9 C 0.32330(19) 0.64840(16) 0.61055(13) 0.0174(3) Uani 1 1 d . . . . .
H9 H 0.3046(5) 0.5703(17) 0.6484(9) 0.021 Uiso 1 1 calc R U . . .
C10 C 0.36449(19) 0.74254(17) 0.66453(13) 0.0190(3) Uani 1 1 d . . . . .
H10A H 0.3735 0.7272 0.7416 0.023 Uiso 1 1 calc R U . . .
C11 C 0.11153(19) 0.92902(16) 0.31328(13) 0.0171(3) Uani 1 1 d . . . . .
O1 O -0.01552(14) 1.00984(13) 0.33936(11) 0.0248(3) Uani 1 1 d . . . . .
C12 C 0.31048(18) 0.79936(16) 0.12143(14) 0.0177(3) Uani 1 1 d . . . . .
O2 O 0.31451(15) 0.79835(13) 0.02531(10) 0.0256(3) Uani 1 1 d . . . . .
C13 C 0.39245(18) 0.95415(16) 0.23020(13) 0.0171(3) Uani 1 1 d . . . . .
O3 O 0.43936(15) 1.04665(13) 0.19829(11) 0.0262(3) Uani 1 1 d . . . . .
C14 C 0.54143(18) 0.67123(16) 0.22403(12) 0.0158(3) Uani 1 1 d . . . . .
N4 N 0.67294(16) 0.59690(15) 0.19763(11) 0.0207(3) Uani 1 1 d . . . . .
C15 C 0.37843(18) 0.87823(16) 0.49246(13) 0.0162(3) Uani 1 1 d . . . . .
H15A H 0.3981 0.9583 0.4518 0.019 Uiso 1 1 calc R U . . .
C16 C 0.1685(2) 0.54300(17) 0.17377(13) 0.0193(3) Uani 1 1 d . . . . .
H16A H 0.1441 0.6411 0.1432 0.023 Uiso 1 1 calc R U . . .
H16B H 0.0743 0.5135 0.1817 0.023 Uiso 1 1 calc R U . . .
C17 C 0.3118(2) 0.4425(2) 0.08996(15) 0.0296(4) Uani 1 1 d . . . . .
H17A H 0.2886 0.4451 0.0149 0.044 Uiso 1 1 calc R U . . .
H17B H 0.3347 0.3451 0.1195 0.044 Uiso 1 1 calc R U . . .
H17C H 0.4047 0.4724 0.0813 0.044 Uiso 1 1 calc R U . . .
C18 C 0.39223(18) 0.85920(17) 0.60453(13) 0.0182(3) Uani 1 1 d . . . . .
H18A H 0.4203 0.9251 0.6399 0.022 Uiso 1 1 calc R U . . .
C19 C -0.1641(14) 0.8301(15) 0.0218(11) 0.028(2) Uani 0.52(2) 1 d D U P A 1
H19A H -0.2197 0.9070 -0.0247 0.033 Uiso 0.52(2) 1 calc R U P A 1
H19B H -0.2374 0.7772 0.0580 0.033 Uiso 0.52(2) 1 calc R U P A 1
Cl1 Cl -0.1242(11) 0.9086(12) 0.1316(7) 0.0300(12) Uani 0.52(2) 1 d D U P A 1
Cl2 Cl 0.0077(4) 0.7123(5) -0.0711(3) 0.0335(7) Uani 0.52(2) 1 d D U P A 1
C19' C -0.1811(17) 0.8247(19) 0.0323(12) 0.029(3) Uani 0.48(2) 1 d D U P A 2
H19C H -0.2126 0.7449 0.0728 0.035 Uiso 0.48(2) 1 calc R U P A 2
H19D H -0.2728 0.8905 0.0055 0.035 Uiso 0.48(2) 1 calc R U P A 2
Cl1' Cl -0.1296(12) 0.9172(14) 0.1284(9) 0.0301(12) Uani 0.48(2) 1 d D U P A 2
Cl2' Cl -0.0148(12) 0.7577(17) -0.0870(7) 0.0577(19) Uani 0.48(2) 1 d D U P A 2


_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 C12 1.8096(16) . ?
Mn1 C11 1.8221(16) . ?
Mn1 C13 1.8299(16) . ?
Mn1 C14 1.9972(16) . ?
Mn1 C1 2.0003(15) . ?
Mn1 N3 2.0745(12) . ?
N1 C1 1.3433(18) . ?
N1 C2 1.3992(18) . ?
N1 C16 1.4666(18) . ?
N2 C1 1.3847(18) . ?
N2 C8 1.4012(18) . ?
N2 C7 1.4089(18) . ?
N3 C8 1.3523(18) . ?
N3 C15 1.3503(19) . ?
C2 C7 1.395(2) . ?
C2 C3 1.392(2) . ?
C3 C4 1.392(2) . ?
C4 C5 1.394(2) . ?
C5 C6 1.394(2) . ?
C6 C7 1.395(2) . ?
C8 C9 1.390(2) . ?
C9 C10 1.387(2) . ?
C10 C18 1.385(2) . ?
C11 O1 1.145(2) . ?
C12 O2 1.1484(19) . ?
C13 O3 1.1485(19) . ?
C14 N4 1.153(2) . ?
C15 C18 1.381(2) . ?
C16 C17 1.515(2) . ?
C19 Cl1 1.767(9) . ?
C19 Cl2 1.762(9) . ?
C19' Cl2' 1.767(11) . ?
C19' Cl1' 1.783(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
C12 Mn1 C11 92.85(7) . . ?
C12 Mn1 C13 87.46(7) . . ?
C11 Mn1 C13 91.18(7) . . ?
C12 Mn1 C14 87.79(6) . . ?
C11 Mn1 C14 179.30(7) . . ?
C13 Mn1 C14 88.55(6) . . ?
C12 Mn1 C1 97.87(6) . . ?
C11 Mn1 C1 92.97(6) . . ?
C13 Mn1 C1 173.07(6) . . ?
C14 Mn1 C1 87.23(6) . . ?
C12 Mn1 N3 173.51(6) . . ?
C11 Mn1 N3 92.31(6) . . ?
C13 Mn1 N3 96.38(6) . . ?
C14 Mn1 N3 87.08(5) . . ?
C1 Mn1 N3 77.93(5) . . ?
C1 N1 C2 111.29(12) . . ?
C1 N1 C16 125.88(12) . . ?
C2 N1 C16 122.76(12) . . ?
C1 N2 C8 117.44(12) . . ?
C1 N2 C7 111.15(12) . . ?
C8 N2 C7 131.31(12) . . ?
C8 N3 C15 117.20(13) . . ?
C8 N3 Mn1 116.48(10) . . ?
C15 N3 Mn1 126.32(10) . . ?
N1 C1 N2 105.44(12) . . ?
N1 C1 Mn1 139.43(11) . . ?
N2 C1 Mn1 115.10(10) . . ?
C7 C2 C3 122.45(13) . . ?
C7 C2 N1 107.35(12) . . ?
C3 C2 N1 130.18(14) . . ?
C2 C3 C4 116.55(14) . . ?
C3 C4 C5 121.33(14) . . ?
C6 C5 C4 122.04(14) . . ?
C5 C6 C7 116.77(14) . . ?
C2 C7 C6 120.85(13) . . ?
C2 C7 N2 104.75(12) . . ?
C6 C7 N2 134.40(13) . . ?
N3 C8 C9 123.13(13) . . ?
N3 C8 N2 112.75(12) . . ?
C9 C8 N2 124.11(13) . . ?
C10 C9 C8 118.45(14) . . ?
C18 C10 C9 119.11(14) . . ?
O1 C11 Mn1 177.96(14) . . ?
O2 C12 Mn1 175.83(14) . . ?
O3 C13 Mn1 175.64(14) . . ?
N4 C14 Mn1 178.01(14) . . ?
N3 C15 C18 123.11(14) . . ?
N1 C16 C17 110.96(14) . . ?
C15 C18 C10 118.99(14) . . ?
Cl1 C19 Cl2 114.1(7) . . ?
Cl2' C19' Cl1' 109.2(8) . . ?

_refine_diff_density_max         0.433
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.063

_shelxl_version_number           2013-3

