# Electronic Supplementary Material (ESI) for Faraday Discussions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_test_a
_database_code_depnum_ccdc_archive 'CCDC 1061485'
_audit_update_record             
;
2015-04-23 deposited with the CCDC.
2015-06-11 downloaded from the CCDC.
;
_audit_creation_date             2015-04-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H8 Br Mn N2 O5'
_chemical_formula_sum            'C13 H8 Br Mn N2 O5'
_chemical_formula_weight         407.06
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_symmetry_space_group_name_H-M_alt 'P 1 21/c 1'
_cell_length_a                   15.1341(2)
_cell_length_b                   13.1528(2)
_cell_length_c                   7.05370(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.591(2)
_cell_angle_gamma                90
_cell_volume                     1388.33(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_cell_oxdiff_angle_alpha         89.982(2)
_cell_oxdiff_angle_beta          98.561(2)
_cell_oxdiff_angle_gamma         90.004(3)
_cell_oxdiff_length_a            15.1282(5)
_cell_oxdiff_length_b            13.1529(4)
_cell_oxdiff_length_c            7.05592(19)
_cell_oxdiff_measurement_reflns_used 12996
_cell_oxdiff_volume              1388.33(7)
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.854
_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            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.948
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            20916
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.994
_diffrn_reflns_theta_min         2.061
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -110.00   15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.0000  -68.0000    0.0000 125

#__ type_ start__ end____ width___ exp.time_
  2 omega -110.00   15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.0000  -68.0000  120.0000 125

#__ type_ start__ end____ width___ exp.time_
  3 omega -110.00   15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.0000  -68.0000  240.0000 125

#__ type_ start__ end____ width___ exp.time_
  4 omega -110.00   15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.0000  -30.0000   90.0000 125
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_UB_11      -0.0182223000
_diffrn_orient_matrix_UB_12      0.0494488000
_diffrn_orient_matrix_UB_13      0.0049290000
_diffrn_orient_matrix_UB_21      -0.0411009000
_diffrn_orient_matrix_UB_22      -0.0171755000
_diffrn_orient_matrix_UB_23      -0.0516713000
_diffrn_orient_matrix_UB_31      -0.0150597000
_diffrn_orient_matrix_UB_32      -0.0129608000
_diffrn_orient_matrix_UB_33      0.0874083000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_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                3815
_reflns_number_total             4417
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.93
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.700
_refine_diff_density_min         -0.990
_refine_diff_density_rms         0.121
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         4417
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0359
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0504P)²+1.3888P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0962
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00G(H00G), C00H(H00H), C00I(H00I), C00M(H00M)
2.b Idealised tetrahedral OH refined as rotating group:
 O003(H003), O006(H006)
;
_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
Br01 Br 0.29905(2) 0.49142(2) 0.07291(3) 0.01604(8) Uani 1 1 d . . . . .
Mn02 Mn 0.21894(2) 0.43829(3) 0.35190(5) 0.01221(9) Uani 1 1 d . . . . .
O003 O 0.13014(12) 0.89496(13) 0.3175(3) 0.0190(4) Uani 1 1 d . . . . .
H003 H 0.1734 0.9274 0.3690 0.028 Uiso 1 1 calc GR . . . .
O004 O 0.30123(13) 0.23528(14) 0.3394(3) 0.0233(4) Uani 1 1 d . . . . .
O005 O 0.06952(12) 0.36610(15) 0.0663(3) 0.0230(4) Uani 1 1 d . . . . .
O006 O 0.52988(12) 0.66208(14) 0.8452(3) 0.0229(4) Uani 1 1 d . . . . .
H006 H 0.5737 0.6259 0.8770 0.034 Uiso 1 1 calc GR . . . .
O007 O 0.11864(13) 0.37280(15) 0.6573(3) 0.0256(4) Uani 1 1 d . . . . .
N008 N 0.32372(14) 0.50187(14) 0.5281(3) 0.0130(4) Uani 1 1 d . . . . .
N009 N 0.17877(13) 0.58577(15) 0.3572(3) 0.0135(4) Uani 1 1 d . . . . .
C00A C 0.32266(15) 0.60430(17) 0.5412(3) 0.0136(4) Uani 1 1 d . . . . .
C00B C 0.14745(16) 0.79506(18) 0.3370(3) 0.0151(4) Uani 1 1 d . . . . .
C00C C 0.39481(16) 0.45268(18) 0.6243(3) 0.0152(4) Uani 1 1 d . . . . .
H00C H 0.3959 0.3821 0.6177 0.018 Uiso 1 1 calc R . . . .
C00D C 0.22811(16) 0.75646(17) 0.4293(3) 0.0140(4) Uani 1 1 d . . . . .
H00D H 0.2729 0.8002 0.4848 0.017 Uiso 1 1 calc R . . . .
C00E C 0.26921(16) 0.31362(18) 0.3459(3) 0.0162(4) Uani 1 1 d . . . . .
C00F C 0.46459(16) 0.60689(19) 0.7424(3) 0.0168(4) Uani 1 1 d . . . . .
C00G C 0.08123(16) 0.72649(18) 0.2606(3) 0.0157(4) Uani 1 1 d . . . . .
H00G H 0.0257 0.7495 0.2022 0.019 Uiso 1 1 calc R . . . .
C00H C 0.39185(16) 0.65908(18) 0.6464(4) 0.0164(4) Uani 1 1 d . . . . .
H00H H 0.3893 0.7296 0.6521 0.020 Uiso 1 1 calc R . . . .
C00I C 0.46582(16) 0.50114(17) 0.7315(4) 0.0155(4) Uani 1 1 d . . . . .
H00I H 0.5136 0.4642 0.7954 0.019 Uiso 1 1 calc R . . . .
C00J C 0.24102(15) 0.65256(17) 0.4378(3) 0.0130(4) Uani 1 1 d . . . . .
C00K C 0.15906(16) 0.39981(18) 0.5418(4) 0.0176(5) Uani 1 1 d . . . . .
C00L C 0.12699(16) 0.39486(18) 0.1769(4) 0.0163(4) Uani 1 1 d . . . . .
C00M C 0.09981(16) 0.62416(18) 0.2733(3) 0.0154(4) Uani 1 1 d . . . . .
H00M H 0.0555 0.5789 0.2212 0.018 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br01 Mn02 2.5582(4) . ?
Mn02 N008 2.042(2) . ?
Mn02 N009 2.035(2) . ?
Mn02 C00E 1.811(3) . ?
Mn02 C00K 1.798(3) . ?
Mn02 C00L 1.809(2) . ?
O003 H003 0.8200 . ?
O003 C00B 1.343(3) . ?
O004 C00E 1.143(3) . ?
O005 C00L 1.143(3) . ?
O006 H006 0.8200 . ?
O006 C00F 1.347(3) . ?
O007 C00K 1.146(3) . ?
N008 C00A 1.351(3) . ?
N008 C00C 1.348(3) . ?
N009 C00J 1.350(3) . ?
N009 C00M 1.350(3) . ?
C00A C00H 1.390(3) . ?
C00A C00J 1.481(3) . ?
C00B C00D 1.391(3) . ?
C00B C00G 1.395(3) . ?
C00C H00C 0.9300 . ?
C00C C00I 1.375(3) . ?
C00D H00D 0.9300 . ?
C00D C00J 1.380(3) . ?
C00F C00H 1.386(3) . ?
C00F C00I 1.393(3) . ?
C00G H00G 0.9300 . ?
C00G C00M 1.375(3) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00M H00M 0.9300 . ?

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
N008 Mn02 Br01 86.69(6) . . ?
N009 Mn02 Br01 86.03(6) . . ?
N009 Mn02 N008 78.78(8) . . ?
C00E Mn02 Br01 88.88(8) . . ?
C00E Mn02 N008 95.41(9) . . ?
C00E Mn02 N009 172.47(10) . . ?
C00K Mn02 Br01 177.90(8) . . ?
C00K Mn02 N008 95.38(10) . . ?
C00K Mn02 N009 93.99(10) . . ?
C00K Mn02 C00E 91.31(11) . . ?
C00K Mn02 C00L 89.86(11) . . ?
C00L Mn02 Br01 88.06(8) . . ?
C00L Mn02 N008 173.12(9) . . ?
C00L Mn02 N009 96.43(9) . . ?
C00L Mn02 C00E 88.93(11) . . ?
C00B O003 H003 109.5 . . ?
C00F O006 H006 109.5 . . ?
C00A N008 Mn02 115.72(16) . . ?
C00C N008 Mn02 126.75(16) . . ?
C00C N008 C00A 117.4(2) . . ?
C00J N009 Mn02 115.88(15) . . ?
C00M N009 Mn02 126.58(16) . . ?
C00M N009 C00J 117.2(2) . . ?
N008 C00A C00H 122.5(2) . . ?
N008 C00A C00J 114.3(2) . . ?
C00H C00A C00J 123.2(2) . . ?
O003 C00B C00D 123.3(2) . . ?
O003 C00B C00G 118.4(2) . . ?
C00D C00B C00G 118.3(2) . . ?
N008 C00C H00C 118.2 . . ?
N008 C00C C00I 123.6(2) . . ?
C00I C00C H00C 118.2 . . ?
C00B C00D H00D 120.3 . . ?
C00J C00D C00B 119.4(2) . . ?
C00J C00D H00D 120.3 . . ?
O004 C00E Mn02 178.9(2) . . ?
O006 C00F C00H 117.5(2) . . ?
O006 C00F C00I 123.6(2) . . ?
C00H C00F C00I 118.9(2) . . ?
C00B C00G H00G 120.7 . . ?
C00M C00G C00B 118.6(2) . . ?
C00M C00G H00G 120.7 . . ?
C00A C00H H00H 120.5 . . ?
C00F C00H C00A 119.0(2) . . ?
C00F C00H H00H 120.5 . . ?
C00C C00I C00F 118.5(2) . . ?
C00C C00I H00I 120.7 . . ?
C00F C00I H00I 120.7 . . ?
N009 C00J C00A 114.0(2) . . ?
N009 C00J C00D 122.7(2) . . ?
C00D C00J C00A 123.2(2) . . ?
O007 C00K Mn02 177.1(2) . . ?
O005 C00L Mn02 179.0(2) . . ?
N009 C00M C00G 123.6(2) . . ?
N009 C00M H00M 118.2 . . ?
C00G C00M H00M 118.2 . . ?

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
Mn02 N008 C00A C00H -176.14(18) . . . . ?
Mn02 N008 C00A C00J 5.1(3) . . . . ?
Mn02 N008 C00C C00I 175.86(18) . . . . ?
Mn02 N009 C00J C00A -10.9(2) . . . . ?
Mn02 N009 C00J C00D 171.04(18) . . . . ?
Mn02 N009 C00M C00G -171.08(18) . . . . ?
O003 C00B C00D C00J -178.1(2) . . . . ?
O003 C00B C00G C00M 177.4(2) . . . . ?
O006 C00F C00H C00A -179.1(2) . . . . ?
O006 C00F C00I C00C 179.1(2) . . . . ?
N008 C00A C00H C00F -0.3(4) . . . . ?
N008 C00A C00J N009 3.8(3) . . . . ?
N008 C00A C00J C00D -178.2(2) . . . . ?
N008 C00C C00I C00F 0.2(4) . . . . ?
C00A N008 C00C C00I -0.9(4) . . . . ?
C00B C00D C00J N009 1.0(3) . . . . ?
C00B C00D C00J C00A -176.8(2) . . . . ?
C00B C00G C00M N009 0.4(4) . . . . ?
C00C N008 C00A C00H 0.9(3) . . . . ?
C00C N008 C00A C00J -177.8(2) . . . . ?
C00D C00B C00G C00M -2.5(3) . . . . ?
C00G C00B C00D C00J 1.8(3) . . . . ?
C00H C00A C00J N009 -175.0(2) . . . . ?
C00H C00A C00J C00D 3.0(4) . . . . ?
C00H C00F C00I C00C 0.5(4) . . . . ?
C00I C00F C00H C00A -0.4(4) . . . . ?
C00J N009 C00M C00G 2.3(3) . . . . ?
C00J C00A C00H C00F 178.3(2) . . . . ?
C00M N009 C00J C00A 175.0(2) . . . . ?
C00M N009 C00J C00D -3.0(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Light-sensitive
