# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_cmpd5syn_p15288
_database_code_depnum_ccdc_archive 'CCDC 2005315'
loop_
_audit_author_name
_audit_author_address
'  Michael K. Takase and  Lawrence M. Henling  and Victor W. Day'
;California Institute of Technology and University of Kansas
United States of America
;
_audit_update_record             
;
2020-05-22 deposited with the CCDC.	2021-01-12 downloaded from the CCDC.
;
_audit_creation_date             2020-05-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H6 Br2 Mn2 N4 O6, 0.25(C12 O4)'
_chemical_formula_sum            'C17 H6 Br2 Mn2 N4 O7'
_chemical_formula_weight         647.96
_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 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn -0.5299 2.8052 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           63
_space_group_name_H-M_alt        'C m c m'
_space_group_name_Hall           '-C 2c 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z-1/2'
'x, -y, z-1/2'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, -z-1/2'
'x+1/2, -y+1/2, z-1/2'
'-x+1/2, y+1/2, z'

_cell_length_a                   17.597(3)
_cell_length_b                   10.830(2)
_cell_length_c                   11.8313(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2254.8(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1195
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      70.68
_cell_measurement_theta_min      4.79
_shelx_estimated_absorpt_T_max   0.684
_shelx_estimated_absorpt_T_min   0.341
_exptl_absorpt_coefficient_mu    13.687
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.909
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1087
_diffrn_reflns_av_unetI/netI     0.1018
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4267
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        66.000
_diffrn_reflns_theta_max         74.214
_diffrn_reflns_theta_min         4.794
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                798
_reflns_number_total             1178
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.973
_refine_diff_density_min         -1.134
_refine_diff_density_rms         0.182
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1178
_refine_ls_number_restraints     29
_refine_ls_R_factor_all          0.1106
_refine_ls_R_factor_gt           0.0616
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0632P)²+11.2199P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1538
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C1S-C2S = C1S-C3S
 1.51 with sigma of 0.02
3. Restrained planarity
 O1S, C1S, C2S, C3S
 with sigma of 0.1
4. Rigid bond restraints
 O1S, C1S, C2S, C3S
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
5. Uiso/Uaniso restraints and constraints
O1S \\sim C1S \\sim C2S \\sim C3S: within 2A with sigma of 0.02 and sigma for
terminal atoms of 0.04 within 2A
6. Same fragment restrains
{O1S, C1S, C3S, C2S} sigma for 1-2: 0.02, 1-3: 0.04
as in
{O1S, C1S, C2S, C3S}
7. Others
 Fixed Sof: C1S(0.25) C2S(0.25)
8.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Br1 Br 0.64197(6) 0.41957(12) 0.7500 0.0250(4) Uani 1 2 d S T P . .
Mn1 Mn 0.65839(9) 0.65084(18) 0.7500 0.0238(5) Uani 1 2 d S T P . .
N1 N 0.5684(3) 0.6555(6) 0.6386(5) 0.0211(15) Uani 1 1 d . . . . .
C1 C 0.5676(4) 0.6564(8) 0.5244(7) 0.0251(18) Uani 1 1 d . . . . .
H1 H 0.6143 0.6564 0.4841 0.030 Uiso 1 1 calc R U . . .
C2 C 0.5000 0.6573(11) 0.4655(10) 0.025(3) Uani 1 2 d S T P . .
H2 H 0.5000 0.6586 0.3853 0.030 Uiso 1 2 calc R U P . .
C3 C 0.5000 0.6556(10) 0.6885(9) 0.021(2) Uani 1 2 d S T P . .
C11 C 0.6647(6) 0.8172(13) 0.7500 0.032(3) Uani 1 2 d S T P . .
O1 O 0.6685(5) 0.9236(9) 0.7500 0.043(2) Uani 1 2 d S T P . .
C12 C 0.7320(4) 0.6428(9) 0.8561(7) 0.033(2) Uani 1 1 d . . . . .
O2 O 0.7796(3) 0.6364(6) 0.9237(5) 0.0385(16) Uani 1 1 d . . . . .
O1S O 0.5000 0.9042(17) 0.7500 0.092(6) Uani 1 4 d DS TU P A 1
C1S C 0.5000 1.001(3) 0.697(3) 0.100(8) Uani 0.5 2 d DS TU P A 1
C2S C 0.5000 1.005(4) 0.571(3) 0.124(12) Uani 0.5 2 d DS TU P A 1
C3S C 0.5000 1.125(2) 0.7500 0.119(11) Uani 1 4 d DS TU P A 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Mn1 2.521(2) . ?
Mn1 N1 2.062(6) . ?
Mn1 N1 2.062(6) 10_557 ?
Mn1 C11 1.805(14) . ?
Mn1 C12 1.806(9) . ?
Mn1 C12 1.806(9) 10_557 ?
N1 C1 1.351(10) . ?
N1 C3 1.340(7) . ?
C1 H1 0.9500 . ?
C1 C2 1.379(9) . ?
C2 C1 1.379(9) 12_655 ?
C2 H2 0.9500 . ?
C3 N1 1.340(7) 12_655 ?
C3 C3 1.46(2) 10_557 ?
C11 O1 1.154(15) . ?
C12 O2 1.160(10) . ?
O1S C1S 1.22(4) . ?
C1S C2S 1.494(16) . ?
C1S C3S 1.487(16) . ?

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 Br1 86.34(19) 10_557 . ?
N1 Mn1 Br1 86.34(19) . . ?
N1 Mn1 N1 79.5(3) 10_557 . ?
C11 Mn1 Br1 176.9(4) . . ?
C11 Mn1 N1 91.3(3) . 10_557 ?
C11 Mn1 N1 91.3(3) . . ?
C11 Mn1 C12 90.2(4) . 10_557 ?
C11 Mn1 C12 90.2(4) . . ?
C12 Mn1 Br1 92.0(3) 10_557 . ?
C12 Mn1 Br1 92.0(3) . . ?
C12 Mn1 N1 175.4(3) . . ?
C12 Mn1 N1 96.2(3) 10_557 . ?
C12 Mn1 N1 175.4(3) 10_557 10_557 ?
C12 Mn1 N1 96.2(3) . 10_557 ?
C12 Mn1 C12 88.1(5) 10_557 . ?
C1 N1 Mn1 130.3(5) . . ?
C3 N1 Mn1 114.1(5) . . ?
C3 N1 C1 115.6(7) . . ?
N1 C1 H1 119.6 . . ?
N1 C1 C2 120.9(8) . . ?
C2 C1 H1 119.6 . . ?
C1 C2 C1 119.3(10) . 12_655 ?
C1 C2 H2 120.3 12_655 . ?
C1 C2 H2 120.3 . . ?
N1 C3 N1 127.7(10) . 12_655 ?
N1 C3 C3 116.2(5) 12_655 10_557 ?
N1 C3 C3 116.2(5) . 10_557 ?
O1 C11 Mn1 179.8(10) . . ?
O2 C12 Mn1 179.2(9) . . ?
O1S C1S C2S 122(2) . . ?
O1S C1S C3S 124(2) . . ?
C3S C1S C2S 113(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Mn1 N1 C1 C2 178.8(7) . . . . ?
Mn1 N1 C3 N1 -178.4(8) . . . 12_655 ?
Mn1 N1 C3 C3 1.5(7) . . . 10_557 ?
N1 C1 C2 C1 -0.5(18) . . . 12_655 ?
C1 N1 C3 N1 0.6(17) . . . 12_655 ?
C1 N1 C3 C3 -179.5(5) . . . 10_557 ?
C3 N1 C1 C2 0.0(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Light-sensitive
####################################################################### 
# 
# 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_cmpd2anti_p15249
_database_code_depnum_ccdc_archive 'CCDC 2005317'
loop_
_audit_author_name
_audit_author_address
'Michael K. Takase'
;California Institute of Technology
United States of America
;
_audit_update_record             
;
2020-10-16 deposited with the CCDC.	2021-01-12 downloaded from the CCDC.
;
_audit_creation_date             2020-05-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H6 Cl2 N4 O6 Re2'
_chemical_formula_sum            'C14 H6 Cl2 N4 O6 Re2'
_chemical_formula_weight         769.53
_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'
Cl Cl 0.1484 0.1585 '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'
Re Re -1.0185 7.2310 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.3386(3)
_cell_length_b                   11.9351(6)
_cell_length_c                   12.3347(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.6407(17)
_cell_angle_gamma                90
_cell_volume                     924.86(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9915
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.967
_cell_measurement_theta_min      2.385
_shelx_estimated_absorpt_T_max   0.775
_shelx_estimated_absorpt_T_min   0.500
_exptl_absorpt_coefficient_mu    13.406
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8522
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.763
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             700
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2.00 -1.00 -1.00 0.0320
0.00 -1.00 1.00 0.0050
0.00 1.00 -1.00 0.0100
0.00 -1.00 -3.00 0.0190
0.00 1.00 3.00 0.0070
3.00 1.00 -1.00 0.0270
-2.00 -1.00 1.00 0.0160
-1.00 1.00 -1.00 0.0120

_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21581
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.992
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_min         2.385
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1535
_reflns_number_total             1634
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         1.570
_refine_diff_density_min         -1.787
_refine_diff_density_rms         0.164
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.401
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1634
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0267
_refine_ls_restrained_S_all      1.401
_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)+5.6995P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0478
_refine_ls_wR_factor_ref         0.0485
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Sof(Cl1A)=Sof(O3A)=Sof(C7A)=1-FVAR(1)
 Sof(Cl1)=Sof(O3)=Sof(C7)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3)
;
_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
Re1 Re 0.47317(4) 0.73689(2) 0.55662(2) 0.01519(9) Uani 1 1 d . . . . .
Cl1 Cl 0.1769(4) 0.6686(3) 0.6481(2) 0.0220(11) Uani 0.795(16) 1 d . . P A 1
Cl1A Cl 0.771(2) 0.7574(19) 0.4522(11) 0.029(5) Uani 0.205(16) 1 d . . P A 2
O1 O 0.2452(8) 0.9472(4) 0.4571(5) 0.0356(13) Uani 1 1 d . . . . .
O2 O 0.6708(8) 0.8832(4) 0.7480(4) 0.0324(13) Uani 1 1 d . . . . .
O3 O 0.8467(14) 0.8044(8) 0.4346(6) 0.0218(18) Uani 0.795(16) 1 d . . P A 1
O3A O 0.103(6) 0.692(3) 0.684(3) 0.042(9) Uiso 0.205(16) 1 d . . P A 2
N1 N 0.3511(8) 0.6131(4) 0.4326(4) 0.0147(12) Uani 1 1 d . . . . .
N2 N 0.3781(8) 0.4214(4) 0.3852(4) 0.0142(11) Uani 1 1 d . . . . .
C1 C 0.2124(10) 0.6295(6) 0.3409(5) 0.0182(15) Uani 1 1 d . . . . .
H1 H 0.1504 0.7014 0.3268 0.022 Uiso 1 1 calc R U . . .
C2 C 0.1596(10) 0.5442(6) 0.2680(5) 0.0204(15) Uani 1 1 d . . . . .
H2 H 0.0664 0.5567 0.2023 0.024 Uiso 1 1 calc R U . . .
C3 C 0.2456(10) 0.4396(6) 0.2928(5) 0.0200(15) Uani 1 1 d . . . . .
H3 H 0.2102 0.3793 0.2434 0.024 Uiso 1 1 calc R U . . .
C4 C 0.4260(10) 0.5095(5) 0.4504(5) 0.0136(13) Uani 1 1 d . . . . .
C5 C 0.3258(10) 0.8682(6) 0.4935(6) 0.0215(15) Uani 1 1 d . . . . .
C6 C 0.5942(10) 0.8287(6) 0.6758(6) 0.0216(15) Uani 1 1 d . . . . .
C7 C 0.705(2) 0.7780(12) 0.4827(11) 0.020(3) Uani 0.795(16) 1 d . . P A 1
C7A C 0.223(6) 0.705(3) 0.629(3) 0.005(9) Uiso 0.205(16) 1 d . . 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
Re1 Cl1 2.455(3) . ?
Re1 Cl1A 2.434(15) . ?
Re1 N1 2.192(5) . ?
Re1 N2 2.189(5) 3_666 ?
Re1 C5 1.934(7) . ?
Re1 C6 1.911(7) . ?
Re1 C7 1.894(15) . ?
Re1 C7A 1.96(4) . ?
O1 C5 1.136(8) . ?
O2 C6 1.156(8) . ?
O3 C7 1.18(2) . ?
O3A C7A 1.09(7) . ?
N1 C1 1.352(8) . ?
N1 C4 1.333(8) . ?
N2 Re1 2.189(5) 3_666 ?
N2 C3 1.340(8) . ?
N2 C4 1.334(8) . ?
C1 H1 0.9500 . ?
C1 C2 1.370(9) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(10) . ?
C3 H3 0.9500 . ?
C4 C4 1.456(12) 3_666 ?

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 Re1 Cl1 82.90(14) . . ?
N1 Re1 Cl1A 85.7(5) . . ?
N2 Re1 Cl1 83.40(15) 3_666 . ?
N2 Re1 Cl1A 86.0(5) 3_666 . ?
N2 Re1 N1 75.15(19) 3_666 . ?
C5 Re1 Cl1 95.5(2) . . ?
C5 Re1 Cl1A 94.2(5) . . ?
C5 Re1 N1 99.1(2) . . ?
C5 Re1 N2 174.3(2) . 3_666 ?
C5 Re1 C7A 88.0(11) . . ?
C6 Re1 Cl1 95.2(2) . . ?
C6 Re1 Cl1A 95.1(5) . . ?
C6 Re1 N1 172.6(3) . . ?
C6 Re1 N2 97.6(2) . 3_666 ?
C6 Re1 C5 88.2(3) . . ?
C6 Re1 C7A 91.5(10) . . ?
C7 Re1 Cl1 175.6(4) . . ?
C7 Re1 N1 93.6(4) . . ?
C7 Re1 N2 93.1(4) . 3_666 ?
C7 Re1 C5 87.7(4) . . ?
C7 Re1 C6 87.9(4) . . ?
C7A Re1 Cl1A 173.1(11) . . ?
C7A Re1 N1 87.5(10) . . ?
C7A Re1 N2 91.2(11) . 3_666 ?
C1 N1 Re1 128.1(4) . . ?
C4 N1 Re1 115.2(4) . . ?
C4 N1 C1 116.8(6) . . ?
C3 N2 Re1 127.7(4) . 3_666 ?
C4 N2 Re1 115.4(4) . 3_666 ?
C4 N2 C3 116.9(6) . . ?
N1 C1 H1 119.5 . . ?
N1 C1 C2 121.1(6) . . ?
C2 C1 H1 119.5 . . ?
C1 C2 H2 120.9 . . ?
C1 C2 C3 118.2(6) . . ?
C3 C2 H2 120.9 . . ?
N2 C3 C2 121.2(6) . . ?
N2 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
N1 C4 N2 125.8(6) . . ?
N1 C4 C4 117.2(7) . 3_666 ?
N2 C4 C4 117.0(7) . 3_666 ?
O1 C5 Re1 177.8(6) . . ?
O2 C6 Re1 178.8(6) . . ?
O3 C7 Re1 178.6(11) . . ?
O3A C7A Re1 169(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Re1 N1 C1 C2 176.5(4) . . . . ?
Re1 N1 C4 N2 -178.5(5) . . . . ?
Re1 N1 C4 C4 1.2(9) . . . 3_666 ?
Re1 N2 C3 C2 178.4(4) 3_666 . . . ?
Re1 N2 C4 N1 -178.7(5) 3_666 . . . ?
Re1 N2 C4 C4 1.6(9) 3_666 . . 3_666 ?
N1 C1 C2 C3 2.5(9) . . . . ?
C1 N1 C4 N2 0.9(9) . . . . ?
C1 N1 C4 C4 -179.4(6) . . . 3_666 ?
C1 C2 C3 N2 -0.3(9) . . . . ?
C3 N2 C4 N1 1.1(9) . . . . ?
C3 N2 C4 C4 -178.6(7) . . . 3_666 ?
C4 N1 C1 C2 -2.7(9) . . . . ?
C4 N2 C3 C2 -1.4(9) . . . . ?

_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_cmpd3_p15315
_database_code_depnum_ccdc_archive 'CCDC 2005320'
loop_
_audit_author_name
_audit_author_address
'  Michael K. Takase and  Lawrence M. Henling  and Victor W. Day'
;California Institute of Technology and University of Kansas
United States of America
;
_audit_update_record             
;
2020-05-22 deposited with the CCDC.	2021-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H6 Br Mn N4 O3'
_chemical_formula_weight         377.05

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                   6.6093(3)
_cell_length_b                   6.6618(3)
_cell_length_c                   14.8504(8)
_cell_angle_alpha                102.3575(17)
_cell_angle_beta                 93.1195(18)
_cell_angle_gamma                102.3828(17)
_cell_volume                     620.40(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9855
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      36.35

_exptl_crystal_description       Block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.018
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    4.296
_shelx_estimated_absorpt_T_min   0.359
_shelx_estimated_absorpt_T_max   0.673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5920
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_process_details   'SADABS-2014/5 (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS HB micro-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            31855
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.173
_diffrn_reflns_theta_max         36.362
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5964
_reflns_number_gt                5046
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX2 v2014.11-0 (Bruker-AXS, 2014)'
_computing_cell_refinement       'SAINT v8.34A (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT v8.34A (Bruker-AXS, 2007)'
_computing_structure_solution    'SHELXS-2013/1 (She ldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0247P)²+0.3776P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5964
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0605
_refine_ls_wR_factor_gt          0.0572
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.75418(2) -0.10899(2) 0.24308(2) 0.01139(4) Uani 1 1 d . . . . .
Mn1 Mn 0.66495(3) 0.22880(3) 0.32549(2) 0.00725(4) Uani 1 1 d . . . . .
N1 N 0.47957(16) 0.19435(17) 0.20721(8) 0.00813(18) Uani 1 1 d . . . . .
C1 C 0.27812(19) 0.0943(2) 0.18835(9) 0.0101(2) Uani 1 1 d . . . . .
H1 H 0.2056 0.0439 0.2356 0.012 Uiso 1 1 calc R U . . .
C2 C 0.1731(2) 0.0628(2) 0.10092(10) 0.0123(2) Uani 1 1 d . . . . .
H2 H 0.0308 -0.0107 0.0898 0.015 Uiso 1 1 calc R U . . .
N3 N 0.26607(19) 0.1327(2) 0.03195(8) 0.0142(2) Uani 1 1 d . . . . .
C3 C 0.4662(2) 0.2351(2) 0.05120(9) 0.0121(2) Uani 1 1 d . . . . .
H3 H 0.5368 0.2885 0.0042 0.015 Uiso 1 1 calc R U . . .
C4 C 0.57503(19) 0.2662(2) 0.13809(9) 0.0084(2) Uani 1 1 d . . . . .
C5 C 0.79405(19) 0.3743(2) 0.16316(9) 0.0086(2) Uani 1 1 d . . . . .
C6 C 0.9210(2) 0.4652(2) 0.10363(9) 0.0117(2) Uani 1 1 d . . . . .
H6 H 0.8638 0.4547 0.0423 0.014 Uiso 1 1 calc R U . . .
N4 N 1.11997(18) 0.56647(19) 0.12946(8) 0.0126(2) Uani 1 1 d . . . . .
C7 C 1.1905(2) 0.5804(2) 0.21765(10) 0.0115(2) Uani 1 1 d . . . . .
H7 H 1.3302 0.6537 0.2395 0.014 Uiso 1 1 calc R U . . .
C8 C 1.0660(2) 0.4912(2) 0.27813(9) 0.0108(2) Uani 1 1 d . . . . .
H8 H 1.1225 0.5065 0.3401 0.013 Uiso 1 1 calc R U . . .
N2 N 0.86821(17) 0.38420(17) 0.25106(8) 0.00818(18) Uani 1 1 d . . . . .
C11 C 0.5930(2) 0.4676(2) 0.38384(9) 0.0114(2) Uani 1 1 d . . . . .
O1 O 0.54033(18) 0.61222(18) 0.42110(8) 0.0184(2) Uani 1 1 d . . . . .
C12 C 0.4658(2) 0.0746(2) 0.37988(9) 0.0105(2) Uani 1 1 d . . . . .
O2 O 0.33855(16) -0.02108(17) 0.41312(8) 0.0164(2) Uani 1 1 d . . . . .
C13 C 0.8577(2) 0.2471(2) 0.42167(10) 0.0126(2) Uani 1 1 d . . . . .
O3 O 0.97877(18) 0.25707(19) 0.48131(8) 0.0203(2) 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
Br1 Mn1 2.5255(2) . ?
Mn1 C11 1.8132(14) . ?
Mn1 C12 1.8253(14) . ?
Mn1 C13 1.8272(14) . ?
Mn1 N1 2.0277(11) . ?
Mn1 N2 2.0379(11) . ?
N1 C1 1.3396(16) . ?
N1 C4 1.3537(16) . ?
C1 C2 1.3908(19) . ?
C1 H1 0.9500 . ?
C2 N3 1.3391(19) . ?
C2 H2 0.9500 . ?
N3 C3 1.3364(18) . ?
C3 C4 1.3948(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.4602(18) . ?
C5 N2 1.3522(16) . ?
C5 C6 1.3943(18) . ?
C6 N4 1.3361(17) . ?
C6 H6 0.9500 . ?
N4 C7 1.3432(18) . ?
C7 C8 1.3912(19) . ?
C7 H7 0.9500 . ?
C8 N2 1.3414(16) . ?
C8 H8 0.9500 . ?
C11 O1 1.1365(17) . ?
C12 O2 1.1431(17) . ?
C13 O3 1.1420(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 Mn1 C12 89.42(6) . . ?
C11 Mn1 C13 92.22(6) . . ?
C12 Mn1 C13 89.89(6) . . ?
C11 Mn1 N1 94.01(5) . . ?
C12 Mn1 N1 95.01(5) . . ?
C13 Mn1 N1 172.11(5) . . ?
C11 Mn1 N2 93.25(5) . . ?
C12 Mn1 N2 173.63(5) . . ?
C13 Mn1 N2 95.78(5) . . ?
N1 Mn1 N2 79.04(4) . . ?
C11 Mn1 Br1 178.36(4) . . ?
C12 Mn1 Br1 89.40(4) . . ?
C13 Mn1 Br1 88.92(4) . . ?
N1 Mn1 Br1 84.96(3) . . ?
N2 Mn1 Br1 87.81(3) . . ?
C1 N1 C4 117.15(11) . . ?
C1 N1 Mn1 126.75(9) . . ?
C4 N1 Mn1 115.89(8) . . ?
N1 C1 C2 121.23(12) . . ?
N1 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
N3 C2 C1 122.14(12) . . ?
N3 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
C3 N3 C2 116.59(12) . . ?
N3 C3 C4 122.17(13) . . ?
N3 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
N1 C4 C3 120.71(12) . . ?
N1 C4 C5 114.44(11) . . ?
C3 C4 C5 124.84(12) . . ?
N2 C5 C6 121.00(12) . . ?
N2 C5 C4 114.78(11) . . ?
C6 C5 C4 124.20(12) . . ?
N4 C6 C5 122.62(13) . . ?
N4 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
C6 N4 C7 115.91(12) . . ?
N4 C7 C8 122.28(12) . . ?
N4 C7 H7 118.9 . . ?
C8 C7 H7 118.9 . . ?
N2 C8 C7 121.59(12) . . ?
N2 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 N2 C5 116.54(11) . . ?
C8 N2 Mn1 128.01(9) . . ?
C5 N2 Mn1 115.44(8) . . ?
O1 C11 Mn1 177.12(12) . . ?
O2 C12 Mn1 178.86(12) . . ?
O3 C13 Mn1 179.38(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 C2 1.07(18) . . . . ?
Mn1 N1 C1 C2 -173.38(9) . . . . ?
N1 C1 C2 N3 -0.9(2) . . . . ?
C1 C2 N3 C3 0.0(2) . . . . ?
C2 N3 C3 C4 0.8(2) . . . . ?
C1 N1 C4 C3 -0.33(18) . . . . ?
Mn1 N1 C4 C3 174.73(10) . . . . ?
C1 N1 C4 C5 179.80(11) . . . . ?
Mn1 N1 C4 C5 -5.13(14) . . . . ?
N3 C3 C4 N1 -0.6(2) . . . . ?
N3 C3 C4 C5 179.22(13) . . . . ?
N1 C4 C5 N2 0.61(16) . . . . ?
C3 C4 C5 N2 -179.25(12) . . . . ?
N1 C4 C5 C6 -178.42(12) . . . . ?
C3 C4 C5 C6 1.7(2) . . . . ?
N2 C5 C6 N4 -0.3(2) . . . . ?
C4 C5 C6 N4 178.71(12) . . . . ?
C5 C6 N4 C7 -1.51(19) . . . . ?
C6 N4 C7 C8 1.35(19) . . . . ?
N4 C7 C8 N2 0.6(2) . . . . ?
C7 C8 N2 C5 -2.36(18) . . . . ?
C7 C8 N2 Mn1 176.45(10) . . . . ?
C6 C5 N2 C8 2.19(17) . . . . ?
C4 C5 N2 C8 -176.87(11) . . . . ?
C6 C5 N2 Mn1 -176.78(10) . . . . ?
C4 C5 N2 Mn1 4.16(14) . . . . ?

_refine_diff_density_max         0.778
_refine_diff_density_min         -0.708
_refine_diff_density_rms         0.110


_chemical_properties_physical    Light-sensitive
####################################################################### 
# 
# 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_cmpd5anti_p15287
_database_code_depnum_ccdc_archive 'CCDC 2005321'
loop_
_audit_author_name
_audit_author_address
'  Michael K. Takase and  Lawrence M. Henling  and Victor W. Day'
;California Institute of Technology and University of Kansas
United States of America
;
_audit_update_record             
;
2020-05-22 deposited with the CCDC.	2021-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H6 Br2 Mn2 N4 O6'
_chemical_formula_weight         595.93

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn -0.5299 2.8052 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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                   6.4380(6)
_cell_length_b                   8.3336(7)
_cell_length_c                   9.4980(9)
_cell_angle_alpha                98.880(7)
_cell_angle_beta                 100.604(7)
_cell_angle_gamma                96.117(7)
_cell_volume                     490.08(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2120
_cell_measurement_theta_min      4.81
_cell_measurement_theta_max      74.57

_exptl_crystal_description       Block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.019
_exptl_crystal_F_000             286
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    15.626
_shelx_estimated_absorpt_T_min   0.408
_shelx_estimated_absorpt_T_max   0.651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5580
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_process_details   'SADABS-2014/5 (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I\mS HB micro-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            5479
_diffrn_reflns_av_unetI/netI     0.0967
_diffrn_reflns_av_R_equivalents  0.0917
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.814
_diffrn_reflns_theta_max         72.057
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1911
_reflns_number_gt                1392
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX2 v2014.11-0 (Bruker-AXS, 2014)'
_computing_cell_refinement       'SAINT v8.34A (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT v8.34A (Bruker-AXS, 2007)'
_computing_structure_solution    'SHELXS-2013/1 (She ldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0823P)²+2.2627P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1911
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1034
_refine_ls_R_factor_gt           0.0702
_refine_ls_wR_factor_ref         0.1759
_refine_ls_wR_factor_gt          0.1569
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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
Br1 Br 0.10970(17) 0.16807(12) 0.35440(11) 0.0239(3) Uani 1 1 d . . . . .
Mn1 Mn 0.4096(2) 0.27149(16) 0.24326(14) 0.0146(4) Uani 1 1 d . . . . .
N1 N 0.3479(11) 0.5020(8) 0.3235(7) 0.0135(14) Uani 1 1 d . . . . .
C1 C 0.2278(16) 0.6009(12) 0.2604(10) 0.025(2) Uani 1 1 d . . . . .
H1 H 0.1629 0.5699 0.1602 0.030 Uiso 1 1 calc R U . . .
C2 C 0.1942(16) 0.7479(10) 0.3363(10) 0.022(2) Uani 1 1 d . . . . .
H2 H 0.1070 0.8171 0.2894 0.026 Uiso 1 1 calc R U . . .
C3 C 0.2895(14) 0.7920(11) 0.4811(9) 0.0164(17) Uani 1 1 d . . . . .
H3 H 0.2686 0.8929 0.5348 0.020 Uiso 1 1 calc R U . . .
N2 N 0.4125(11) 0.6932(9) 0.5478(7) 0.0148(15) Uani 1 1 d . . . . .
C4 C 0.4334(14) 0.5532(11) 0.4667(9) 0.0170(18) Uani 1 1 d . . . . .
C11 C 0.6248(15) 0.3568(12) 0.1609(10) 0.024(2) Uani 1 1 d . . . . .
O1 O 0.7458(13) 0.4045(9) 0.1031(8) 0.0331(17) Uani 1 1 d . . . . .
C12 C 0.2205(18) 0.2454(12) 0.0710(11) 0.027(2) Uani 1 1 d . . . . .
O2 O 0.1004(13) 0.2263(9) -0.0366(7) 0.0356(18) Uani 1 1 d . . . . .
C13 C 0.4671(15) 0.0651(11) 0.1906(9) 0.0206(19) Uani 1 1 d . . . . .
O3 O 0.5027(12) -0.0654(8) 0.1547(7) 0.0269(15) 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
Br1 Mn1 2.5025(17) . ?
Mn1 C13 1.812(10) . ?
Mn1 C12 1.818(11) . ?
Mn1 C11 1.843(10) . ?
Mn1 N2 2.061(7) 2_666 ?
Mn1 N1 2.061(7) . ?
N1 C1 1.325(12) . ?
N1 C4 1.353(11) . ?
C1 C2 1.381(13) . ?
C1 H1 0.9500 . ?
C2 C3 1.375(13) . ?
C2 H2 0.9500 . ?
C3 N2 1.349(11) . ?
C3 H3 0.9500 . ?
N2 C4 1.330(11) . ?
N2 Mn1 2.061(7) 2_666 ?
C4 C4 1.435(17) 2_666 ?
C11 O1 1.107(12) . ?
C12 O2 1.141(13) . ?
C13 O3 1.148(12) . ?

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 C12 88.7(4) . . ?
C13 Mn1 C11 91.1(4) . . ?
C12 Mn1 C11 90.7(4) . . ?
C13 Mn1 N2 95.5(3) . 2_666 ?
C12 Mn1 N2 171.8(4) . 2_666 ?
C11 Mn1 N2 96.2(3) . 2_666 ?
C13 Mn1 N1 174.5(3) . . ?
C12 Mn1 N1 95.8(4) . . ?
C11 Mn1 N1 92.1(4) . . ?
N2 Mn1 N1 79.7(3) 2_666 . ?
C13 Mn1 Br1 91.4(3) . . ?
C12 Mn1 Br1 88.4(3) . . ?
C11 Mn1 Br1 177.2(3) . . ?
N2 Mn1 Br1 84.50(19) 2_666 . ?
N1 Mn1 Br1 85.43(19) . . ?
C1 N1 C4 115.8(7) . . ?
C1 N1 Mn1 130.5(6) . . ?
C4 N1 Mn1 113.5(5) . . ?
N1 C1 C2 121.9(9) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C3 C2 C1 118.6(8) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
N2 C3 C2 120.6(8) . . ?
N2 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C4 N2 C3 116.6(7) . . ?
C4 N2 Mn1 113.1(6) . 2_666 ?
C3 N2 Mn1 130.3(6) . 2_666 ?
N2 C4 N1 126.5(8) . . ?
N2 C4 C4 118.0(10) . 2_666 ?
N1 C4 C4 115.4(9) . 2_666 ?
O1 C11 Mn1 175.6(8) . . ?
O2 C12 Mn1 178.8(10) . . ?
O3 C13 Mn1 178.8(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 C2 0.7(14) . . . . ?
Mn1 N1 C1 C2 175.3(7) . . . . ?
N1 C1 C2 C3 0.3(15) . . . . ?
C1 C2 C3 N2 -0.3(14) . . . . ?
C2 C3 N2 C4 -0.6(13) . . . . ?
C2 C3 N2 Mn1 175.8(6) . . . 2_666 ?
C3 N2 C4 N1 1.7(13) . . . . ?
Mn1 N2 C4 N1 -175.3(7) 2_666 . . . ?
C3 N2 C4 C4 178.7(10) . . . 2_666 ?
Mn1 N2 C4 C4 1.7(13) 2_666 . . 2_666 ?
C1 N1 C4 N2 -1.7(13) . . . . ?
Mn1 N1 C4 N2 -177.3(7) . . . . ?
C1 N1 C4 C4 -178.8(10) . . . 2_666 ?
Mn1 N1 C4 C4 5.6(13) . . . 2_666 ?

_refine_diff_density_max         1.451
_refine_diff_density_min         -0.966
_refine_diff_density_rms         0.218


_chemical_properties_physical    Light-sensitive
####################################################################### 
# 
# 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_cmpd4_p15260
_database_code_depnum_ccdc_archive 'CCDC 2005318'
loop_
_audit_author_name
_audit_author_address
'  Michael K. Takase and  Lawrence M. Henling  and Victor W. Day'
;California Institute of Technology and University of Kansas
United States of America
;
_audit_update_record             
;
2020-05-22 deposited with the CCDC.	2021-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H6 Br Mn N4 O3'
_chemical_formula_weight         377.05

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                   6.4216(2)
_cell_length_b                   14.7565(6)
_cell_length_c                   13.5124(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.0331(12)
_cell_angle_gamma                90
_cell_volume                     1252.30(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9954
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      37.42

_exptl_crystal_description       Block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.000
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    4.257
_shelx_estimated_absorpt_T_min   0.416
_shelx_estimated_absorpt_T_max   0.815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5901
_exptl_absorpt_correction_T_max  0.7474
_exptl_absorpt_process_details   'SADABS-2014/5 (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS HB micro-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            28709
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.083
_diffrn_reflns_theta_max         36.307
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6048
_reflns_number_gt                4910
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX2 v2014.11-0 (Bruker-AXS, 2014)'
_computing_cell_refinement       'SAINT v8.34A (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT v8.34A (Bruker-AXS, 2007)'
_computing_structure_solution    'SHELXS-2013/1 (She ldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0275P)²+0.9326P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6048
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0687
_refine_ls_wR_factor_gt          0.0638
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.26853(2) 0.70326(2) 0.77820(2) 0.01269(4) Uani 1 1 d . . . . .
Mn1 Mn 0.38131(3) 0.65874(2) 0.61607(2) 0.00951(5) Uani 1 1 d . . . . .
O1 O 0.5096(2) 0.59824(9) 0.43054(10) 0.0215(2) Uani 1 1 d . . . . .
O2 O 0.0900(2) 0.50234(8) 0.60767(9) 0.0189(2) Uani 1 1 d . . . . .
O3 O 0.73171(19) 0.54481(9) 0.72924(9) 0.0201(2) Uani 1 1 d . . . . .
N1 N 0.15780(19) 0.74610(8) 0.53908(9) 0.0102(2) Uani 1 1 d . . . . .
N2 N 0.54568(19) 0.77858(8) 0.63322(9) 0.0103(2) Uani 1 1 d . . . . .
N3 N 0.0883(2) 0.90330(9) 0.50500(10) 0.0137(2) Uani 1 1 d . . . . .
N4 N 0.5011(2) 0.93821(9) 0.60817(10) 0.0142(2) Uani 1 1 d . . . . .
C1 C -0.0375(2) 0.72561(10) 0.48472(12) 0.0128(2) Uani 1 1 d . . . . .
H1 H -0.0804 0.6640 0.4769 0.015 Uiso 1 1 calc R U . . .
C2 C -0.1767(2) 0.79275(10) 0.44003(11) 0.0135(3) Uani 1 1 d . . . . .
H2 H -0.3136 0.7783 0.4011 0.016 Uiso 1 1 calc R U . . .
C3 C -0.1085(2) 0.88195(11) 0.45427(12) 0.0145(3) Uani 1 1 d . . . . .
H3 H -0.2038 0.9293 0.4273 0.017 Uiso 1 1 calc R U . . .
C4 C 0.2119(2) 0.83462(10) 0.54380(11) 0.0109(2) Uani 1 1 d . . . . .
C5 C 0.4327(2) 0.85321(9) 0.59829(11) 0.0107(2) Uani 1 1 d . . . . .
C6 C 0.7029(3) 0.95046(11) 0.65774(12) 0.0155(3) Uani 1 1 d . . . . .
H6 H 0.7585 1.0103 0.6661 0.019 Uiso 1 1 calc R U . . .
C7 C 0.8336(2) 0.87821(11) 0.69738(12) 0.0145(3) Uani 1 1 d . . . . .
H7 H 0.9762 0.8877 0.7326 0.017 Uiso 1 1 calc R U . . .
C8 C 0.7478(2) 0.79216(10) 0.68343(11) 0.0127(2) Uani 1 1 d . . . . .
H8 H 0.8329 0.7415 0.7097 0.015 Uiso 1 1 calc R U . . .
C11 C 0.4595(2) 0.62345(10) 0.49951(13) 0.0144(3) Uani 1 1 d . . . . .
C12 C 0.2030(2) 0.56279(10) 0.60946(11) 0.0133(3) Uani 1 1 d . . . . .
C13 C 0.5962(2) 0.58979(10) 0.68728(11) 0.0130(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
Br1 Mn1 2.5332(3) . ?
Mn1 C12 1.8115(16) . ?
Mn1 C13 1.8197(15) . ?
Mn1 C11 1.8257(17) . ?
Mn1 N1 2.0450(12) . ?
Mn1 N2 2.0478(12) . ?
O1 C11 1.112(2) . ?
O2 C12 1.1470(19) . ?
O3 C13 1.1462(19) . ?
N1 C1 1.3489(19) . ?
N1 C4 1.3497(19) . ?
N2 C8 1.3484(19) . ?
N2 C5 1.3488(18) . ?
N3 C4 1.3262(19) . ?
N3 C3 1.343(2) . ?
N4 C5 1.3265(19) . ?
N4 C6 1.342(2) . ?
C1 C2 1.386(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.388(2) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 C5 1.481(2) . ?
C6 C7 1.393(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.381(2) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?

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 89.48(7) . . ?
C12 Mn1 C11 91.10(7) . . ?
C13 Mn1 C11 88.98(7) . . ?
C12 Mn1 N1 95.64(6) . . ?
C13 Mn1 N1 174.81(6) . . ?
C11 Mn1 N1 91.77(6) . . ?
C12 Mn1 N2 170.48(6) . . ?
C13 Mn1 N2 96.14(6) . . ?
C11 Mn1 N2 96.66(6) . . ?
N1 Mn1 N2 78.68(5) . . ?
C12 Mn1 Br1 87.34(5) . . ?
C13 Mn1 Br1 90.56(5) . . ?
C11 Mn1 Br1 178.37(5) . . ?
N1 Mn1 Br1 88.83(3) . . ?
N2 Mn1 Br1 84.93(4) . . ?
C1 N1 C4 116.34(12) . . ?
C1 N1 Mn1 127.58(10) . . ?
C4 N1 Mn1 116.08(9) . . ?
C8 N2 C5 116.49(13) . . ?
C8 N2 Mn1 127.20(10) . . ?
C5 N2 Mn1 116.01(10) . . ?
C4 N3 C3 116.38(13) . . ?
C5 N4 C6 116.29(13) . . ?
N1 C1 C2 121.26(14) . . ?
N1 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
C1 C2 C3 117.49(14) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
N3 C3 C2 121.95(14) . . ?
N3 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
N3 C4 N1 126.44(14) . . ?
N3 C4 C5 119.17(13) . . ?
N1 C4 C5 114.40(12) . . ?
N4 C5 N2 126.45(14) . . ?
N4 C5 C4 119.19(13) . . ?
N2 C5 C4 114.36(12) . . ?
N4 C6 C7 122.06(14) . . ?
N4 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C8 C7 C6 117.38(14) . . ?
C8 C7 H7 121.3 . . ?
C6 C7 H7 121.3 . . ?
N2 C8 C7 121.33(14) . . ?
N2 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
O1 C11 Mn1 176.81(14) . . ?
O2 C12 Mn1 178.36(14) . . ?
O3 C13 Mn1 177.73(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 C2 -2.5(2) . . . . ?
Mn1 N1 C1 C2 177.03(11) . . . . ?
N1 C1 C2 C3 -0.7(2) . . . . ?
C4 N3 C3 C2 -2.2(2) . . . . ?
C1 C2 C3 N3 3.2(2) . . . . ?
C3 N3 C4 N1 -1.5(2) . . . . ?
C3 N3 C4 C5 178.38(13) . . . . ?
C1 N1 C4 N3 3.9(2) . . . . ?
Mn1 N1 C4 N3 -175.76(12) . . . . ?
C1 N1 C4 C5 -176.03(13) . . . . ?
Mn1 N1 C4 C5 4.35(16) . . . . ?
C6 N4 C5 N2 0.1(2) . . . . ?
C6 N4 C5 C4 -179.59(13) . . . . ?
C8 N2 C5 N4 0.3(2) . . . . ?
Mn1 N2 C5 N4 174.46(12) . . . . ?
C8 N2 C5 C4 -179.99(13) . . . . ?
Mn1 N2 C5 C4 -5.81(16) . . . . ?
N3 C4 C5 N4 0.8(2) . . . . ?
N1 C4 C5 N4 -179.28(13) . . . . ?
N3 C4 C5 N2 -178.94(13) . . . . ?
N1 C4 C5 N2 0.96(18) . . . . ?
C5 N4 C6 C7 -0.4(2) . . . . ?
N4 C6 C7 C8 0.3(2) . . . . ?
C5 N2 C8 C7 -0.4(2) . . . . ?
Mn1 N2 C8 C7 -173.84(11) . . . . ?
C6 C7 C8 N2 0.2(2) . . . . ?

_refine_diff_density_max         0.969
_refine_diff_density_min         -0.693
_refine_diff_density_rms         0.121


_chemical_properties_physical    Light-sensitive
####################################################################### 
# 
# 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_cmpd6syn_p15317
_database_code_depnum_ccdc_archive 'CCDC 2005319'
loop_
_audit_author_name
_audit_author_address
'Michael K. Takase'
;California Institute of Technology
United States of America
;
_audit_update_record             
;
2020-10-16 deposited with the CCDC.	2021-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H12 Br2 Mn N4 O7 Re'
_chemical_formula_weight         785.27

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 '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      orthorhombic
_space_group_IT_number           63
_space_group_name_H-M_alt        'C m c m'
_space_group_name_Hall           '-C 2c 2'

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

_cell_length_a                   17.6165(8)
_cell_length_b                   10.9052(5)
_cell_length_c                   11.8240(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2271.53(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6464
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      31.82

_exptl_crystal_description       Needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.296
_exptl_crystal_F_000             1472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    9.444
_shelx_estimated_absorpt_T_min   0.452
_shelx_estimated_absorpt_T_max   0.765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5762
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_process_details   'SADABS-2014/5 (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS HB micro-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            15274
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.196
_diffrn_reflns_theta_max         30.501
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1811
_reflns_number_gt                1497
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX2 v2014.11-0 (Bruker-AXS, 2014)'
_computing_cell_refinement       'SAINT v8.34A (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT v8.34A (Bruker-AXS, 2007)'
_computing_structure_solution    'SHELXS-2013/1 (She ldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0180P)²+6.7143P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1811
_refine_ls_number_parameters     126
_refine_ls_number_restraints     199
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0286
_refine_ls_wR_factor_ref         0.0519
_refine_ls_wR_factor_gt          0.0489
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.64110(2) 0.41820(4) 0.7500 0.01458(10) Uani 1 2 d S T P . .
Re1 Re 0.66460(14) 0.6548(2) 0.7500 0.01155(17) Uani 0.5 2 d DS TU P A 1
Mn1 Mn 0.6593(5) 0.6453(9) 0.7500 0.01155(17) Uani 0.5 2 d DS TU P A 2
C11 C 0.6708(17) 0.8318(13) 0.7500 0.013(3) Uani 0.5 2 d DS TU P A 1
O1 O 0.6716(15) 0.9371(14) 0.7500 0.022(3) Uani 0.5 2 d DS TU P A 1
C12 C 0.7451(9) 0.651(2) 0.8596(18) 0.013(3) Uani 0.5 1 d D U P A 1
O2 O 0.7918(11) 0.648(2) 0.926(2) 0.020(2) Uani 0.5 1 d D U P A 1
C11A C 0.6650(18) 0.8124(15) 0.7500 0.018(3) Uani 0.5 2 d DS TU P A 2
O1A O 0.6675(19) 0.9173(16) 0.7500 0.040(5) Uani 0.5 2 d DS TU P A 2
C12A C 0.7310(10) 0.636(2) 0.8603(19) 0.016(3) Uani 0.5 1 d D U P A 2
O2A O 0.7782(11) 0.631(2) 0.927(2) 0.028(3) Uani 0.5 1 d D U P A 2
N1 N 0.56789(13) 0.6552(2) 0.63755(19) 0.0127(5) Uani 1 1 d . . . . .
C1 C 0.56750(16) 0.6568(2) 0.5240(2) 0.0155(6) Uani 1 1 d . . . . .
H1 H 0.6143 0.6578 0.4840 0.019 Uiso 1 1 calc R U . . .
C2 C 0.5000 0.6570(4) 0.4643(3) 0.0169(8) Uani 1 2 d S T P . .
H2 H 0.5000 0.6573 0.3840 0.020 Uiso 1 2 calc R U P . .
C3 C 0.5000 0.6538(3) 0.6887(3) 0.0120(7) Uani 1 2 d S T P A .
O1S O 0.5000 0.8982(5) 0.7500 0.0549(17) Uani 1 4 d DS TU P B 1
C1S C 0.5000 0.9919(9) 0.7080(10) 0.049(3) Uani 0.5 2 d DS TU P B 1
C2S C 0.5000 0.9980(13) 0.5850(12) 0.090(5) Uani 0.5 2 d DS TU P B 1
H2S1 H 0.5000 1.0840 0.5609 0.135 Uiso 0.5 2 calc R U P B 1
H2S2 H 0.5454 0.9570 0.5556 0.135 Uiso 0.25 1 calc R U P B 1
H2S3 H 0.4546 0.9570 0.5556 0.135 Uiso 0.25 1 calc R U P B 1
C3S C 0.5000 1.1123(8) 0.7500 0.115(5) Uani 1 4 d DS TU P B 1
H3S1 H 0.5000 1.1703 0.6867 0.173 Uiso 0.5 2 calc R U P B 1
H3S2 H 0.4546 1.1253 0.7963 0.173 Uiso 0.25 1 calc R U P B 1
H3S3 H 0.5454 1.1253 0.7963 0.173 Uiso 0.25 1 calc R U P B 1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Mn1 2.497(9) . ?
Br1 Re1 2.614(2) . ?
Re1 C12 1.921(12) . ?
Re1 C12 1.921(12) 10_557 ?
Re1 C11 1.933(14) . ?
Re1 N1 2.161(3) 10_557 ?
Re1 N1 2.161(3) . ?
Mn1 C12A 1.818(15) 10_557 ?
Mn1 C12A 1.818(15) . ?
Mn1 C11A 1.825(16) . ?
Mn1 N1 2.092(8) 10_557 ?
Mn1 N1 2.092(8) . ?
C11 O1 1.148(11) . ?
C12 O2 1.141(10) . ?
C11A O1A 1.145(12) . ?
C12A O2A 1.151(10) . ?
N1 C3 1.340(3) . ?
N1 C1 1.343(3) . ?
C1 C2 1.382(3) . ?
C1 H1 0.9500 . ?
C2 C1 1.382(3) 12_655 ?
C2 H2 0.9500 . ?
C3 N1 1.340(3) 12_655 ?
C3 C3 1.451(7) 10_557 ?
O1S C1S 1.136(11) . ?
C1S C3S 1.404(10) . ?
C1S C2S 1.456(12) . ?
C2S H2S1 0.9800 . ?
C2S H2S2 0.9800 . ?
C2S H2S3 0.9800 . ?
C3S H3S1 0.9800 . ?
C3S H3S2 0.9800 . ?
C3S H3S3 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 Re1 C12 84.9(14) . 10_557 ?
C12 Re1 C11 88.7(9) . . ?
C12 Re1 C11 88.7(9) 10_557 . ?
C12 Re1 N1 99.6(7) . 10_557 ?
C12 Re1 N1 175.4(7) 10_557 10_557 ?
C11 Re1 N1 92.5(7) . 10_557 ?
C12 Re1 N1 175.4(7) . . ?
C12 Re1 N1 99.6(7) 10_557 . ?
C11 Re1 N1 92.5(7) . . ?
N1 Re1 N1 75.94(14) 10_557 . ?
C12 Re1 Br1 95.6(7) . . ?
C12 Re1 Br1 95.6(7) 10_557 . ?
C11 Re1 Br1 174.1(9) . . ?
N1 Re1 Br1 82.94(8) 10_557 . ?
N1 Re1 Br1 82.94(8) . . ?
C12A Mn1 C12A 91.7(16) 10_557 . ?
C12A Mn1 C11A 90.9(11) 10_557 . ?
C12A Mn1 C11A 90.9(11) . . ?
C12A Mn1 N1 173.6(8) 10_557 10_557 ?
C12A Mn1 N1 94.7(8) . 10_557 ?
C11A Mn1 N1 89.4(9) . 10_557 ?
C12A Mn1 N1 94.7(8) 10_557 . ?
C12A Mn1 N1 173.6(8) . . ?
C11A Mn1 N1 89.4(9) . . ?
N1 Mn1 N1 78.9(4) 10_557 . ?
C12A Mn1 Br1 92.0(8) 10_557 . ?
C12A Mn1 Br1 92.0(8) . . ?
C11A Mn1 Br1 175.7(11) . . ?
N1 Mn1 Br1 87.3(3) 10_557 . ?
N1 Mn1 Br1 87.3(3) . . ?
O1 C11 Re1 177(2) . . ?
O2 C12 Re1 178.3(17) . . ?
O1A C11A Mn1 179(2) . . ?
O2A C12A Mn1 177.7(18) . . ?
C3 N1 C1 116.5(3) . . ?
C3 N1 Mn1 113.6(2) . . ?
C1 N1 Mn1 129.8(3) . . ?
C3 N1 Re1 115.23(19) . . ?
C1 N1 Re1 128.3(2) . . ?
N1 C1 C2 121.0(3) . . ?
N1 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
C1 C2 C1 118.7(4) . 12_655 ?
C1 C2 H2 120.7 . . ?
C1 C2 H2 120.7 12_655 . ?
N1 C3 N1 126.4(3) . 12_655 ?
N1 C3 C3 116.80(17) . 10_557 ?
N1 C3 C3 116.80(17) 12_655 10_557 ?
O1S C1S C3S 133.3(10) . . ?
O1S C1S C2S 118.6(9) . . ?
C3S C1S C2S 108.1(9) . . ?
C1S C2S H2S1 109.5 . . ?
C1S C2S H2S2 109.5 . . ?
H2S1 C2S H2S2 109.5 . . ?
C1S C2S H2S3 109.5 . . ?
H2S1 C2S H2S3 109.5 . . ?
H2S2 C2S H2S3 109.5 . . ?
C1S C3S H3S1 109.5 . . ?
C1S C3S H3S2 109.5 . . ?
H3S1 C3S H3S2 109.5 . . ?
C1S C3S H3S3 109.5 . . ?
H3S1 C3S H3S3 109.5 . . ?
H3S2 C3S H3S3 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 C2 0.1(4) . . . . ?
Mn1 N1 C1 C2 176.4(4) . . . . ?
Re1 N1 C1 C2 -179.9(2) . . . . ?
N1 C1 C2 C1 0.6(6) . . . 12_655 ?
C1 N1 C3 N1 -0.8(5) . . . 12_655 ?
Mn1 N1 C3 N1 -177.8(4) . . . 12_655 ?
Re1 N1 C3 N1 179.1(3) . . . 12_655 ?
C1 N1 C3 C3 -179.18(17) . . . 10_557 ?
Mn1 N1 C3 C3 3.9(4) . . . 10_557 ?
Re1 N1 C3 C3 0.8(2) . . . 10_557 ?

_refine_diff_density_max         0.892
_refine_diff_density_min         -1.442
_refine_diff_density_rms         0.161

####################################################################### 
# 
# 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_cmpd1_a15100
_database_code_depnum_ccdc_archive 'CCDC 2005316'
loop_
_audit_author_name
_audit_author_address
'  Michael K. Takase and  Lawrence M. Henling  and Victor W. Day'
;California Institute of Technology and University of Kansas
United States of America
;
_audit_update_record             
;
2020-05-22 deposited with the CCDC.	2021-01-12 downloaded from the CCDC.
;
_audit_creation_date             2020-05-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H6 Cl N4 O3 Re'
_chemical_formula_sum            'C11 H6 Cl N4 O3 Re'
_chemical_formula_weight         463.85
_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'
Cl Cl 0.1484 0.1585 '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'
Re Re -1.0185 7.2310 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.2872(3)
_cell_length_b                   14.9679(7)
_cell_length_c                   13.4775(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.408(2)
_cell_angle_gamma                90
_cell_volume                     1238.69(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9989
_cell_measurement_temperature    100
_cell_measurement_theta_max      49.15
_cell_measurement_theta_min      2.72
_shelx_estimated_absorpt_T_max   0.824
_shelx_estimated_absorpt_T_min   0.108
_exptl_absorpt_coefficient_mu    10.038
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1152 before and 0.0658 after correction. The Ratio of minimum to maximum transmission is 0.6301. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.487
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       blade
_exptl_crystal_F_000             864
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 0.00 1.00 0.1880
1.00 0.00 -1.00 0.1790
0.00 0.00 1.00 0.0160
0.00 0.00 -1.00 0.0270
0.00 -1.00 0.00 0.0070
0.00 1.00 0.00 0.0080
1.00 1.00 -5.00 0.0760

_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            32945
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.992
_diffrn_reflns_theta_min         2.060
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3459
_reflns_number_total             3602
_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 V8.34A (Bruker-AXS, 2007)'
_computing_data_collection       'APEX2 2014.11-0 (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT V8.34A (Bruker-AXS, 2007)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         1.185
_refine_diff_density_min         -0.905
_refine_diff_density_rms         0.126
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.252
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3602
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0226
_refine_ls_R_factor_gt           0.0212
_refine_ls_restrained_S_all      1.252
_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)+3.5069P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0453
_refine_ls_wR_factor_ref         0.0457
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C11A) = Uanis(Cl1)
3. Others
 Sof(Cl1A)=Sof(O3A)=Sof(C11A)=1-FVAR(1)
 Sof(Cl1)=Sof(O3)=Sof(C11)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C7(H7), C8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Re1 Re 0.61838(2) 0.34643(2) 0.37847(2) 0.01147(4) Uani 1 1 d . . . . .
Cl1 Cl 0.73492(13) 0.29884(6) 0.22178(7) 0.0144(3) Uani 0.944(6) 1 d . . P A 1
Cl1A Cl 0.534(4) 0.3804(18) 0.5330(19) 0.019(6) Uiso 0.056(6) 1 d . . P A 2
O1 O 0.9161(4) 0.51031(16) 0.39549(18) 0.0194(5) Uani 1 1 d . . . . .
O2 O 0.2390(4) 0.46228(18) 0.26640(19) 0.0220(5) Uani 1 1 d . . . . .
O3 O 0.4983(5) 0.39777(19) 0.5797(3) 0.0221(6) Uani 0.944(6) 1 d . . P A 1
O3A O 0.763(9) 0.303(4) 0.174(5) 0.029(12) Uiso 0.056(6) 1 d . . P A 2
N1 N 0.8539(4) 0.25057(17) 0.45785(19) 0.0115(4) Uani 1 1 d . . . . .
N2 N 0.4501(4) 0.21884(17) 0.36027(19) 0.0116(4) Uani 1 1 d . . . . .
N3 N 0.9158(4) 0.09581(18) 0.4928(2) 0.0147(5) Uani 1 1 d . . . . .
N4 N 0.4970(4) 0.06218(18) 0.3881(2) 0.0156(5) Uani 1 1 d . . . . .
C1 C 1.0532(5) 0.2694(2) 0.5130(2) 0.0138(5) Uani 1 1 d . . . . .
H1 H 1.0997 0.3299 0.5208 0.017 Uiso 1 1 calc R U . . .
C2 C 1.1917(5) 0.2028(2) 0.5586(2) 0.0142(5) Uani 1 1 d . . . . .
H2 H 1.3324 0.2162 0.5980 0.017 Uiso 1 1 calc R U . . .
C3 C 1.1179(5) 0.1153(2) 0.5448(2) 0.0160(6) Uani 1 1 d . . . . .
H3 H 1.2126 0.0680 0.5728 0.019 Uiso 1 1 calc R U . . .
C4 C 0.7936(5) 0.1639(2) 0.4529(2) 0.0126(5) Uani 1 1 d . . . . .
C5 C 0.5674(5) 0.1459(2) 0.3969(2) 0.0125(5) Uani 1 1 d . . . . .
C6 C 0.2905(5) 0.0498(2) 0.3384(2) 0.0172(6) Uani 1 1 d . . . . .
H6 H 0.2335 -0.0092 0.3314 0.021 Uiso 1 1 calc R U . . .
C7 C 0.1578(5) 0.1198(2) 0.2968(2) 0.0163(6) Uani 1 1 d . . . . .
H7 H 0.0126 0.1097 0.2607 0.020 Uiso 1 1 calc R U . . .
C8 C 0.2436(5) 0.2050(2) 0.3098(2) 0.0139(5) Uani 1 1 d . . . . .
H8 H 0.1556 0.2545 0.2827 0.017 Uiso 1 1 calc R U . . .
C9 C 0.8034(5) 0.4497(2) 0.3905(2) 0.0154(6) Uani 1 1 d . . . . .
C10 C 0.3832(5) 0.4197(2) 0.3067(2) 0.0147(5) Uani 1 1 d . . . . .
C11 C 0.5416(7) 0.3777(3) 0.5024(5) 0.0160(9) Uani 0.944(6) 1 d . . P A 1
C11A C 0.713(10) 0.319(5) 0.256(6) 0.0144(3) Uani 0.056(6) 1 d . . 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
Re1 Cl1 2.4837(10) . ?
Re1 Cl1A 2.31(3) . ?
Re1 N1 2.171(2) . ?
Re1 N2 2.172(3) . ?
Re1 C9 1.920(3) . ?
Re1 C10 1.926(3) . ?
Re1 C11 1.894(6) . ?
Re1 C11A 1.92(8) . ?
O1 C9 1.145(4) . ?
O2 C10 1.146(4) . ?
O3 C11 1.171(7) . ?
O3A C11A 1.23(11) . ?
N1 C1 1.342(4) . ?
N1 C4 1.349(4) . ?
N2 C5 1.351(4) . ?
N2 C8 1.346(4) . ?
N3 C3 1.345(4) . ?
N3 C4 1.320(4) . ?
N4 C5 1.326(4) . ?
N4 C6 1.340(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.379(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.389(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.484(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.381(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.381(4) . ?
C8 H8 0.9500 . ?

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 Re1 Cl1 86.27(7) . . ?
N1 Re1 Cl1A 88.0(6) . . ?
N1 Re1 N2 74.85(9) . . ?
N2 Re1 Cl1 82.96(7) . . ?
N2 Re1 Cl1A 95.4(6) . . ?
C9 Re1 Cl1 91.06(10) . . ?
C9 Re1 Cl1A 90.0(6) . . ?
C9 Re1 N1 98.84(11) . . ?
C9 Re1 N2 171.52(11) . . ?
C9 Re1 C10 88.28(13) . . ?
C9 Re1 C11A 87(2) . . ?
C10 Re1 Cl1 94.09(10) . . ?
C10 Re1 Cl1A 91.6(6) . . ?
C10 Re1 N1 172.86(11) . . ?
C10 Re1 N2 98.10(11) . . ?
C11 Re1 Cl1 176.54(13) . . ?
C11 Re1 N1 90.27(15) . . ?
C11 Re1 N2 96.12(14) . . ?
C11 Re1 C9 89.50(16) . . ?
C11 Re1 C10 89.34(16) . . ?
C11A Re1 Cl1A 175.3(19) . . ?
C11A Re1 N1 88.8(19) . . ?
C11A Re1 N2 87(2) . . ?
C11A Re1 C10 92.1(18) . . ?
C1 N1 Re1 126.2(2) . . ?
C1 N1 C4 116.7(3) . . ?
C4 N1 Re1 117.14(19) . . ?
C5 N2 Re1 117.06(19) . . ?
C8 N2 Re1 125.9(2) . . ?
C8 N2 C5 116.9(3) . . ?
C4 N3 C3 116.6(3) . . ?
C5 N4 C6 116.4(3) . . ?
N1 C1 H1 119.3 . . ?
N1 C1 C2 121.3(3) . . ?
C2 C1 H1 119.3 . . ?
C1 C2 H2 121.3 . . ?
C1 C2 C3 117.5(3) . . ?
C3 C2 H2 121.3 . . ?
N3 C3 C2 121.7(3) . . ?
N3 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
N1 C4 C5 115.4(3) . . ?
N3 C4 N1 126.1(3) . . ?
N3 C4 C5 118.5(3) . . ?
N2 C5 C4 115.3(3) . . ?
N4 C5 N2 125.8(3) . . ?
N4 C5 C4 118.8(3) . . ?
N4 C6 H6 118.9 . . ?
N4 C6 C7 122.2(3) . . ?
C7 C6 H6 118.9 . . ?
C6 C7 H7 121.2 . . ?
C8 C7 C6 117.7(3) . . ?
C8 C7 H7 121.2 . . ?
N2 C8 C7 120.9(3) . . ?
N2 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
O1 C9 Re1 178.1(3) . . ?
O2 C10 Re1 177.6(3) . . ?
O3 C11 Re1 178.6(4) . . ?
O3A C11A Re1 177(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Re1 N1 C1 C2 -178.6(2) . . . . ?
Re1 N1 C4 N3 177.5(2) . . . . ?
Re1 N1 C4 C5 -2.7(3) . . . . ?
Re1 N2 C5 N4 -176.1(2) . . . . ?
Re1 N2 C5 C4 4.9(3) . . . . ?
Re1 N2 C8 C7 175.3(2) . . . . ?
N1 C1 C2 C3 0.4(5) . . . . ?
N1 C4 C5 N2 -1.4(4) . . . . ?
N1 C4 C5 N4 179.5(3) . . . . ?
N3 C4 C5 N2 178.4(3) . . . . ?
N3 C4 C5 N4 -0.7(4) . . . . ?
N4 C6 C7 C8 -1.2(5) . . . . ?
C1 N1 C4 N3 -3.6(5) . . . . ?
C1 N1 C4 C5 176.2(3) . . . . ?
C1 C2 C3 N3 -2.8(5) . . . . ?
C3 N3 C4 N1 1.2(5) . . . . ?
C3 N3 C4 C5 -178.6(3) . . . . ?
C4 N1 C1 C2 2.6(4) . . . . ?
C4 N3 C3 C2 2.1(5) . . . . ?
C5 N2 C8 C7 0.2(4) . . . . ?
C5 N4 C6 C7 0.9(5) . . . . ?
C6 N4 C5 N2 0.0(5) . . . . ?
C6 N4 C5 C4 178.9(3) . . . . ?
C6 C7 C8 N2 0.7(5) . . . . ?
C8 N2 C5 N4 -0.5(5) . . . . ?
C8 N2 C5 C4 -179.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT430_cmpd1_a15100        
;
PROBLEM: Short Inter D...A Contact  O1       ..O1       .       2.81 Ang.  
RESPONSE: An O---O contact of 2.80 angstroms is neither unusual nor 
problematic since this value is twice the van der Waals radius of oxygen.
;
# end Validation Reply Form

