# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_xsc1373
_database_code_depnum_ccdc_archive 'CCDC 1047275'
_audit_update_record             
;
2015-02-04 deposited with the CCDC.
2015-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H10 Br Cl Mn N O4'
_chemical_formula_weight         510.60

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.099(16)
_cell_length_b                   8.497(17)
_cell_length_c                   16.14(3)
_cell_angle_alpha                77.34(3)
_cell_angle_beta                 75.64(2)
_cell_angle_gamma                70.47(3)
_cell_volume                     1003(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    840
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      18.25

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.691
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    2.811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6516
_exptl_absorpt_correction_T_max  0.7450
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker ApexII'
_diffrn_measurement_method       /w
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            4082
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0745
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.64
_diffrn_reflns_theta_max         23.26
_reflns_number_total             2723
_reflns_number_gt                1499
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'ApexII (Bruker, 2012)'
_computing_cell_refinement       'ApexII (Bruker, 2012)'
_computing_data_reduction        'SAINT (Bruker, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXS (Sheldrick, 2008)'
_computing_publication_material  'SHELXS (Sheldrick, 2008)'

_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     
'calc w=1/[σ²(Fo²)+(0.0755P)²+0.0000P] 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         2723
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1229
_refine_ls_R_factor_gt           0.0593
_refine_ls_wR_factor_ref         0.1616
_refine_ls_wR_factor_gt          0.1295
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.34931(14) 0.54150(12) 0.27280(7) 0.0918(5) Uani 1 1 d . . .
Mn1 Mn 0.13228(17) 0.44674(16) 0.22343(9) 0.0712(5) Uani 1 1 d . . .
Cl1 Cl 0.8479(3) -0.1833(4) -0.00725(17) 0.1095(10) Uani 1 1 d . . .
N1 N 0.2939(8) 0.2040(8) 0.2495(4) 0.0529(16) Uani 1 1 d . . .
C16 C 0.4277(10) 0.1088(10) 0.1875(5) 0.051(2) Uani 1 1 d . . .
O4 O 0.0317(9) 0.3842(10) 0.3550(4) 0.089(2) Uani 1 1 d . . .
O1 O -0.1304(9) 0.3538(11) 0.1652(5) 0.116(3) Uani 1 1 d . . .
C19 C 0.6836(12) -0.0674(13) 0.0662(5) 0.068(2) Uani 1 1 d . . .
C12 C 0.3597(14) -0.0157(13) 0.3846(6) 0.070(3) Uani 1 1 d . . .
C13 C 0.2718(10) 0.1383(10) 0.3298(5) 0.054(2) Uani 1 1 d . . .
C3 C 0.2338(12) 0.4941(12) 0.1123(7) 0.075(3) Uani 1 1 d . . .
C17 C 0.4163(11) -0.0401(11) 0.1723(5) 0.060(2) Uani 1 1 d . . .
H17A H 0.3212 -0.0804 0.2024 0.073 Uiso 1 1 calc R . .
C4 C 0.1248(13) 0.2467(15) 0.3867(6) 0.073(3) Uani 1 1 d . . .
C21 C 0.5652(11) 0.1723(10) 0.1378(5) 0.062(2) Uani 1 1 d . . .
H21A H 0.5705 0.2761 0.1449 0.074 Uiso 1 1 calc R . .
O2 O -0.0975(13) 0.7975(11) 0.2116(6) 0.170(4) Uani 1 1 d . . .
C5 C 0.1224(16) 0.1583(18) 0.4742(7) 0.090(3) Uani 1 1 d . . .
C18 C 0.5467(12) -0.1297(11) 0.1121(6) 0.072(2) Uani 1 1 d . . .
H18A H 0.5412 -0.2320 0.1029 0.086 Uiso 1 1 calc R . .
C1 C -0.0342(14) 0.3870(13) 0.1899(6) 0.085(3) Uani 1 1 d . . .
O3 O 0.2946(10) 0.5285(9) 0.0414(5) 0.115(3) Uani 1 1 d . . .
C20 C 0.6928(11) 0.0811(13) 0.0784(6) 0.071(2) Uani 1 1 d . . .
H20A H 0.7862 0.1222 0.0464 0.085 Uiso 1 1 calc R . .
C11 C 0.5008(15) -0.1576(13) 0.3714(6) 0.082(3) Uani 1 1 d . . .
H11A H 0.5652 -0.1747 0.3161 0.099 Uiso 1 1 calc R . .
C9 C 0.454(3) -0.258(2) 0.5269(11) 0.151(8) Uani 1 1 d . . .
H9A H 0.4877 -0.3409 0.5730 0.182 Uiso 1 1 calc R . .
C15 C 0.2610(17) 0.0068(17) 0.4710(6) 0.090(3) Uani 1 1 d . . .
C14 C 0.313(2) -0.117(2) 0.5418(8) 0.121(6) Uani 1 1 d . . .
C6 C 0.0172(17) 0.1938(19) 0.5550(8) 0.134(5) Uani 1 1 d . . .
H6A H -0.0749 0.2940 0.5609 0.160 Uiso 1 1 calc R . .
C2 C -0.0083(17) 0.6586(17) 0.2164(8) 0.124(5) Uani 1 1 d . . .
C10 C 0.5458(18) -0.2781(14) 0.4450(9) 0.118(4) Uani 1 1 d . . .
H10A H 0.6419 -0.3746 0.4369 0.142 Uiso 1 1 calc R . .
C7 C 0.060(3) 0.065(3) 0.6295(13) 0.177(13) Uani 1 1 d . . .
H7A H -0.0154 0.0789 0.6830 0.213 Uiso 1 1 calc R . .
C8 C 0.197(3) -0.066(3) 0.6237(13) 0.174(11) Uani 1 1 d . . .
H8A H 0.2259 -0.1335 0.6750 0.209 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
Br1 Mn1 2.509(4) . y
Mn1 C2 1.776(13) . y
Mn1 C3 1.797(11) . y
Mn1 C1 1.819(11) . y
Mn1 N1 2.057(7) . y
Mn1 O4 2.096(8) . y
Cl1 C19 1.731(9) . ?
N1 C13 1.288(9) . ?
N1 C16 1.435(9) . ?
C16 C17 1.377(10) . ?
C16 C21 1.394(10) . ?
O4 C4 1.239(11) . ?
O1 C1 1.094(10) . ?
C19 C20 1.347(12) . ?
C19 C18 1.369(11) . ?
C12 C11 1.369(12) . ?
C12 C15 1.444(13) . ?
C12 C13 1.478(12) . ?
C13 C4 1.486(12) . ?
C3 O3 1.144(10) . ?
C17 C18 1.384(10) . ?
C4 C5 1.444(14) . ?
C21 C20 1.374(11) . ?
O2 C2 1.157(11) . ?
C5 C15 1.398(14) . ?
C5 C6 1.404(14) . ?
C11 C10 1.423(13) . ?
C9 C10 1.360(19) . ?
C9 C14 1.37(2) . ?
C15 C14 1.414(16) . ?
C14 C8 1.48(2) . ?
C6 C7 1.46(2) . ?
C7 C8 1.29(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 Mn1 C3 88.2(5) . . y
C2 Mn1 C1 89.0(5) . . y
C3 Mn1 C1 90.4(4) . . y
C2 Mn1 N1 171.8(4) . . y
C3 Mn1 N1 98.5(4) . . y
C1 Mn1 N1 95.5(4) . . y
C2 Mn1 O4 94.4(5) . . y
C3 Mn1 O4 176.0(4) . . y
C1 Mn1 O4 92.7(4) . . y
N1 Mn1 O4 78.7(3) . . y
C2 Mn1 Br1 88.3(4) . . y
C3 Mn1 Br1 90.9(3) . . y
C1 Mn1 Br1 177.1(3) . . y
N1 Mn1 Br1 87.0(2) . . y
O4 Mn1 Br1 86.2(2) . . y
C13 N1 C16 119.4(7) . . ?
C13 N1 Mn1 114.7(5) . . ?
C16 N1 Mn1 125.9(5) . . ?
C17 C16 C21 119.1(7) . . ?
C17 C16 N1 120.9(7) . . ?
C21 C16 N1 119.9(7) . . ?
C4 O4 Mn1 111.9(6) . . ?
C20 C19 C18 120.8(8) . . ?
C20 C19 Cl1 120.0(8) . . ?
C18 C19 Cl1 119.2(8) . . ?
C11 C12 C15 119.9(10) . . ?
C11 C12 C13 136.0(9) . . ?
C15 C12 C13 104.1(9) . . ?
N1 C13 C12 137.6(8) . . ?
N1 C13 C4 114.2(8) . . ?
C12 C13 C4 108.1(8) . . ?
O3 C3 Mn1 178.0(9) . . ?
C16 C17 C18 119.9(8) . . ?
O4 C4 C5 132.9(11) . . ?
O4 C4 C13 119.9(9) . . ?
C5 C4 C13 107.2(10) . . ?
C20 C21 C16 119.8(8) . . ?
C15 C5 C6 118.2(13) . . ?
C15 C5 C4 107.4(9) . . ?
C6 C5 C4 134.3(14) . . ?
C19 C18 C17 119.8(8) . . ?
O1 C1 Mn1 176.1(10) . . ?
C19 C20 C21 120.5(8) . . ?
C12 C11 C10 117.8(11) . . ?
C10 C9 C14 120.4(13) . . ?
C5 C15 C14 127.2(13) . . ?
C5 C15 C12 113.2(10) . . ?
C14 C15 C12 119.6(13) . . ?
C9 C14 C15 119.4(14) . . ?
C9 C14 C8 130.3(18) . . ?
C15 C14 C8 110.3(17) . . ?
C5 C6 C7 116.6(15) . . ?
O2 C2 Mn1 178.9(12) . . ?
C9 C10 C11 122.8(13) . . ?
C8 C7 C6 122(2) . . ?
C7 C8 C14 125(2) . . ?

_diffrn_measured_fraction_theta_max 0.951
_diffrn_reflns_theta_full        23.26
_diffrn_measured_fraction_theta_full 0.951
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.073



_chemical_properties_physical    'Light-sensitive, Photo-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_xsc1395
_database_code_depnum_ccdc_archive 'CCDC 1047276'
_audit_update_record             
;
2015-02-04 deposited with the CCDC.
2015-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H14 Br Cl2 Mn N2 O3'
_chemical_formula_weight         620.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.4714(8)
_cell_length_b                   13.0857(10)
_cell_length_c                   16.9748(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.5820(10)
_cell_angle_gamma                90.00
_cell_volume                     2545.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8836
_cell_measurement_theta_min      2.363
_cell_measurement_theta_max      23.996

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    2.331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5642
_exptl_absorpt_correction_T_max  0.7450
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker ApexII'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            19738
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         24.11
_reflns_number_total             4033
_reflns_number_gt                3695
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEXII (Bruker 2012)'
_computing_cell_refinement       'APEXII (Bruker 2012)'
_computing_data_reduction        'SAINT (Bruker 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 2008)'
_computing_publication_material  'SHELXS (sHLEDRICK, 2008)'

_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     
'calc w=1/[σ²(Fo²)+(0.0584P)²+17.2183P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4033
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0744
_refine_ls_wR_factor_ref         0.1858
_refine_ls_wR_factor_gt          0.1835
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_restrained_S_all      1.193
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.50420(8) 0.73950(7) 0.25303(5) 0.0557(3) Uani 1 1 d . . .
Mn1 Mn 0.59408(9) 0.58741(8) 0.31972(6) 0.0346(3) Uani 1 1 d . . .
Cl1 Cl -0.0251(2) 0.4751(3) 0.39749(18) 0.0880(9) Uani 1 1 d . . .
Cl2 Cl 1.1062(2) 0.6111(3) 0.0755(2) 0.0944(10) Uani 1 1 d . . .
O1 O 0.6877(9) 0.4204(5) 0.3881(7) 0.066(3) Uani 1 1 d . . .
O2 O 0.4992(6) 0.6477(6) 0.4710(4) 0.075(2) Uani 1 1 d . . .
O3 O 0.8043(6) 0.7102(5) 0.3600(5) 0.086(2) Uani 1 1 d . . .
N1 N 0.6485(5) 0.5378(4) 0.2120(3) 0.0327(12) Uani 1 1 d . . .
N2 N 0.4497(5) 0.5072(4) 0.2787(3) 0.0351(13) Uani 1 1 d . . .
C1 C 0.6667(15) 0.4686(9) 0.3727(11) 0.066(3) Uani 1 1 d . . .
C2 C 0.5343(7) 0.6249(6) 0.4122(4) 0.0441(18) Uani 1 1 d . . .
C3 C 0.7236(7) 0.6623(6) 0.3435(5) 0.0493(19) Uani 1 1 d . . .
C4 C 0.5739(5) 0.4812(5) 0.1728(4) 0.0310(14) Uani 1 1 d . . .
C5 C 0.5675(6) 0.4280(5) 0.0968(4) 0.0335(15) Uani 1 1 d . . .
C6 C 0.6376(7) 0.4186(6) 0.0338(4) 0.0428(17) Uani 1 1 d . . .
H6A H 0.7091 0.4521 0.0334 0.051 Uiso 1 1 calc R . .
C7 C 0.5987(7) 0.3569(6) -0.0306(4) 0.0481(19) Uani 1 1 d . . .
H7A H 0.6457 0.3508 -0.0736 0.058 Uiso 1 1 calc R . .
C8 C 0.4949(8) 0.3059(7) -0.0322(5) 0.053(2) Uani 1 1 d . . .
H8A H 0.4732 0.2650 -0.0752 0.064 Uiso 1 1 calc R . .
C9 C 0.3088(8) 0.2698(7) 0.0382(5) 0.056(2) Uani 1 1 d . . .
H9A H 0.2798 0.2262 -0.0013 0.067 Uiso 1 1 calc R . .
C10 C 0.2433(7) 0.2892(7) 0.1014(5) 0.058(2) Uani 1 1 d . . .
H10A H 0.1703 0.2588 0.1035 0.070 Uiso 1 1 calc R . .
C11 C 0.2818(7) 0.3533(6) 0.1637(5) 0.0474(19) Uani 1 1 d . . .
H11A H 0.2353 0.3656 0.2062 0.057 Uiso 1 1 calc R . .
C12 C 0.3893(6) 0.3970(5) 0.1600(4) 0.0358(15) Uani 1 1 d . . .
C13 C 0.4624(6) 0.4632(5) 0.2115(4) 0.0327(15) Uani 1 1 d . . .
C14 C 0.4207(7) 0.3150(6) 0.0313(4) 0.0429(17) Uani 1 1 d . . .
C15 C 0.4584(6) 0.3770(5) 0.0935(4) 0.0345(15) Uani 1 1 d . . .
C16 C 0.7611(6) 0.5554(5) 0.1808(4) 0.0330(15) Uani 1 1 d . . .
C17 C 0.7899(7) 0.6524(6) 0.1560(5) 0.051(2) Uani 1 1 d . . .
H17A H 0.7373 0.7058 0.1608 0.061 Uiso 1 1 calc R . .
C18 C 0.8963(7) 0.6701(7) 0.1240(6) 0.060(2) Uani 1 1 d . . .
H18A H 0.9163 0.7353 0.1074 0.072 Uiso 1 1 calc R . .
C19 C 0.9727(6) 0.5893(7) 0.1172(5) 0.051(2) Uani 1 1 d . . .
C20 C 0.9461(7) 0.4931(7) 0.1440(5) 0.055(2) Uani 1 1 d . . .
H20A H 0.9995 0.4400 0.1407 0.066 Uiso 1 1 calc R . .
C21 C 0.8399(6) 0.4766(6) 0.1757(5) 0.0459(18) Uani 1 1 d . . .
H21A H 0.8210 0.4119 0.1938 0.055 Uiso 1 1 calc R . .
C22 C 0.3372(6) 0.5016(6) 0.3118(4) 0.0359(16) Uani 1 1 d . . .
C23 C 0.3157(7) 0.4348(8) 0.3714(5) 0.062(2) Uani 1 1 d . . .
H23A H 0.3757 0.3950 0.3937 0.074 Uiso 1 1 calc R . .
C24 C 0.2033(8) 0.4269(9) 0.3986(6) 0.076(3) Uani 1 1 d . . .
H24A H 0.1873 0.3805 0.4382 0.091 Uiso 1 1 calc R . .
C25 C 0.1163(7) 0.4878(8) 0.3666(5) 0.055(2) Uani 1 1 d . . .
C26 C 0.1384(7) 0.5584(8) 0.3100(6) 0.061(2) Uani 1 1 d . . .
H26A H 0.0797 0.6021 0.2910 0.073 Uiso 1 1 calc R . .
C27 C 0.2497(7) 0.5642(7) 0.2811(5) 0.052(2) Uani 1 1 d . . .
H27A H 0.2651 0.6102 0.2412 0.062 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
Br1 Mn1 2.4900(14) . y
Mn1 C2 1.808(8) . y
Mn1 C3 1.810(8) . y
Mn1 C1 1.963(15) . y
Mn1 N2 2.056(6) . y
Mn1 N1 2.063(6) . y
Cl1 C25 1.736(8) . ?
Cl2 C19 1.738(8) . ?
O1 C1 0.719(17) . ?
O2 C2 1.134(9) . ?
O3 C3 1.143(9) . ?
N1 C4 1.293(8) . ?
N1 C16 1.436(8) . ?
N2 C13 1.292(9) . ?
N2 C22 1.432(9) . ?
C4 C5 1.464(9) . ?
C4 C13 1.484(9) . ?
C5 C6 1.373(10) . ?
C5 C15 1.418(9) . ?
C6 C7 1.415(10) . ?
C6 H6A 0.9300 . ?
C7 C8 1.364(12) . ?
C7 H7A 0.9300 . ?
C8 C14 1.408(11) . ?
C8 H8A 0.9300 . ?
C9 C10 1.361(12) . ?
C9 C14 1.423(11) . ?
C9 H9A 0.9300 . ?
C10 C11 1.406(11) . ?
C10 H10A 0.9300 . ?
C11 C12 1.364(10) . ?
C11 H11A 0.9300 . ?
C12 C15 1.432(10) . ?
C12 C13 1.467(9) . ?
C14 C15 1.385(10) . ?
C16 C21 1.376(10) . ?
C16 C17 1.382(10) . ?
C17 C18 1.377(11) . ?
C17 H17A 0.9300 . ?
C18 C19 1.382(12) . ?
C18 H18A 0.9300 . ?
C19 C20 1.378(12) . ?
C20 C21 1.371(11) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?
C22 C23 1.369(11) . ?
C22 C27 1.379(11) . ?
C23 C24 1.393(12) . ?
C23 H23A 0.9300 . ?
C24 C25 1.370(13) . ?
C24 H24A 0.9300 . ?
C25 C26 1.365(13) . ?
C26 C27 1.391(11) . ?
C26 H26A 0.9300 . ?
C27 H27A 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
C2 Mn1 C3 90.0(4) . . y
C2 Mn1 C1 89.3(6) . . y
C3 Mn1 C1 90.0(5) . . y
C2 Mn1 N2 95.8(3) . . y
C3 Mn1 N2 173.1(3) . . y
C1 Mn1 N2 94.0(5) . . y
C2 Mn1 N1 174.9(3) . . y
C3 Mn1 N1 95.2(3) . . y
C1 Mn1 N1 91.0(5) . . y
N2 Mn1 N1 79.1(2) . . y
C2 Mn1 Br1 90.7(2) . . y
C3 Mn1 Br1 89.3(3) . . y
C1 Mn1 Br1 179.3(5) . . y
N2 Mn1 Br1 86.74(16) . . y
N1 Mn1 Br1 89.11(15) . . y
C4 N1 C16 119.1(6) . . ?
C4 N1 Mn1 114.6(4) . . ?
C16 N1 Mn1 126.1(4) . . ?
C13 N2 C22 117.6(6) . . ?
C13 N2 Mn1 113.9(4) . . ?
C22 N2 Mn1 128.3(4) . . ?
O1 C1 Mn1 171(3) . . ?
O2 C2 Mn1 178.4(7) . . ?
O3 C3 Mn1 178.5(8) . . ?
N1 C4 C5 137.0(6) . . ?
N1 C4 C13 115.3(6) . . ?
C5 C4 C13 107.7(5) . . ?
C6 C5 C15 118.2(6) . . ?
C6 C5 C4 136.2(6) . . ?
C15 C5 C4 105.6(6) . . ?
C5 C6 C7 118.6(7) . . ?
C5 C6 H6A 120.7 . . ?
C7 C6 H6A 120.7 . . ?
C8 C7 C6 122.6(7) . . ?
C8 C7 H7A 118.7 . . ?
C6 C7 H7A 118.7 . . ?
C7 C8 C14 120.1(7) . . ?
C7 C8 H8A 120.0 . . ?
C14 C8 H8A 120.0 . . ?
C10 C9 C14 121.3(7) . . ?
C10 C9 H9A 119.4 . . ?
C14 C9 H9A 119.4 . . ?
C9 C10 C11 122.6(7) . . ?
C9 C10 H10A 118.7 . . ?
C11 C10 H10A 118.7 . . ?
C12 C11 C10 118.0(7) . . ?
C12 C11 H11A 121.0 . . ?
C10 C11 H11A 121.0 . . ?
C11 C12 C15 119.6(6) . . ?
C11 C12 C13 135.5(7) . . ?
C15 C12 C13 104.9(6) . . ?
N2 C13 C12 134.8(6) . . ?
N2 C13 C4 117.0(6) . . ?
C12 C13 C4 108.1(5) . . ?
C15 C14 C8 117.0(7) . . ?
C15 C14 C9 115.6(7) . . ?
C8 C14 C9 127.3(7) . . ?
C14 C15 C5 123.4(7) . . ?
C14 C15 C12 122.9(6) . . ?
C5 C15 C12 113.6(6) . . ?
C21 C16 C17 120.1(7) . . ?
C21 C16 N1 120.4(6) . . ?
C17 C16 N1 119.5(6) . . ?
C18 C17 C16 120.3(8) . . ?
C18 C17 H17A 119.9 . . ?
C16 C17 H17A 119.9 . . ?
C17 C18 C19 118.7(8) . . ?
C17 C18 H18A 120.6 . . ?
C19 C18 H18A 120.6 . . ?
C20 C19 C18 121.3(7) . . ?
C20 C19 Cl2 119.8(6) . . ?
C18 C19 Cl2 118.9(7) . . ?
C21 C20 C19 119.2(7) . . ?
C21 C20 H20A 120.4 . . ?
C19 C20 H20A 120.4 . . ?
C20 C21 C16 120.3(7) . . ?
C20 C21 H21A 119.9 . . ?
C16 C21 H21A 119.9 . . ?
C23 C22 C27 120.4(7) . . ?
C23 C22 N2 121.2(7) . . ?
C27 C22 N2 118.3(6) . . ?
C22 C23 C24 119.5(8) . . ?
C22 C23 H23A 120.2 . . ?
C24 C23 H23A 120.2 . . ?
C25 C24 C23 119.6(9) . . ?
C25 C24 H24A 120.2 . . ?
C23 C24 H24A 120.2 . . ?
C26 C25 C24 121.2(8) . . ?
C26 C25 Cl1 118.9(7) . . ?
C24 C25 Cl1 119.9(7) . . ?
C25 C26 C27 119.2(8) . . ?
C25 C26 H26A 120.4 . . ?
C27 C26 H26A 120.4 . . ?
C22 C27 C26 119.9(8) . . ?
C22 C27 H27A 120.0 . . ?
C26 C27 H27A 120.0 . . ?

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
C2 Mn1 N1 C4 -1(3) . . . . ?
C3 Mn1 N1 C4 -177.9(5) . . . . ?
C1 Mn1 N1 C4 92.1(6) . . . . ?
N2 Mn1 N1 C4 -1.8(5) . . . . ?
Br1 Mn1 N1 C4 -88.6(5) . . . . ?
C2 Mn1 N1 C16 -177(3) . . . . ?
C3 Mn1 N1 C16 6.0(6) . . . . ?
C1 Mn1 N1 C16 -84.0(7) . . . . ?
N2 Mn1 N1 C16 -177.9(5) . . . . ?
Br1 Mn1 N1 C16 95.2(5) . . . . ?
C2 Mn1 N2 C13 -177.1(5) . . . . ?
C3 Mn1 N2 C13 37(3) . . . . ?
C1 Mn1 N2 C13 -87.5(7) . . . . ?
N1 Mn1 N2 C13 2.8(5) . . . . ?
Br1 Mn1 N2 C13 92.5(5) . . . . ?
C2 Mn1 N2 C22 8.3(6) . . . . ?
C3 Mn1 N2 C22 -137(2) . . . . ?
C1 Mn1 N2 C22 97.9(7) . . . . ?
N1 Mn1 N2 C22 -171.8(6) . . . . ?
Br1 Mn1 N2 C22 -82.1(6) . . . . ?
C2 Mn1 C1 O1 116(16) . . . . ?
C3 Mn1 C1 O1 -154(16) . . . . ?
N2 Mn1 C1 O1 21(16) . . . . ?
N1 Mn1 C1 O1 -59(16) . . . . ?
Br1 Mn1 C1 O1 -156(26) . . . . ?
C3 Mn1 C2 O2 -51(30) . . . . ?
C1 Mn1 C2 O2 39(30) . . . . ?
N2 Mn1 C2 O2 133(30) . . . . ?
N1 Mn1 C2 O2 132(28) . . . . ?
Br1 Mn1 C2 O2 -140(30) . . . . ?
C2 Mn1 C3 O3 -3(33) . . . . ?
C1 Mn1 C3 O3 -92(33) . . . . ?
N2 Mn1 C3 O3 143(32) . . . . ?
N1 Mn1 C3 O3 177(100) . . . . ?
Br1 Mn1 C3 O3 88(33) . . . . ?
C16 N1 C4 C5 -3.6(12) . . . . ?
Mn1 N1 C4 C5 180.0(7) . . . . ?
C16 N1 C4 C13 177.1(6) . . . . ?
Mn1 N1 C4 C13 0.7(7) . . . . ?
N1 C4 C5 C6 -2.6(15) . . . . ?
C13 C4 C5 C6 176.8(8) . . . . ?
N1 C4 C5 C15 178.0(8) . . . . ?
C13 C4 C5 C15 -2.6(7) . . . . ?
C15 C5 C6 C7 -1.3(10) . . . . ?
C4 C5 C6 C7 179.4(8) . . . . ?
C5 C6 C7 C8 -0.5(12) . . . . ?
C6 C7 C8 C14 1.2(13) . . . . ?
C14 C9 C10 C11 -0.7(15) . . . . ?
C9 C10 C11 C12 -0.3(14) . . . . ?
C10 C11 C12 C15 0.4(11) . . . . ?
C10 C11 C12 C13 -177.2(8) . . . . ?
C22 N2 C13 C12 -6.7(12) . . . . ?
Mn1 N2 C13 C12 178.1(7) . . . . ?
C22 N2 C13 C4 171.9(6) . . . . ?
Mn1 N2 C13 C4 -3.3(8) . . . . ?
C11 C12 C13 N2 -2.8(15) . . . . ?
C15 C12 C13 N2 179.3(8) . . . . ?
C11 C12 C13 C4 178.4(8) . . . . ?
C15 C12 C13 C4 0.6(7) . . . . ?
N1 C4 C13 N2 1.8(9) . . . . ?
C5 C4 C13 N2 -177.7(6) . . . . ?
N1 C4 C13 C12 -179.2(6) . . . . ?
C5 C4 C13 C12 1.3(7) . . . . ?
C7 C8 C14 C15 0.0(12) . . . . ?
C7 C8 C14 C9 178.1(8) . . . . ?
C10 C9 C14 C15 1.5(12) . . . . ?
C10 C9 C14 C8 -176.6(9) . . . . ?
C8 C14 C15 C5 -1.8(11) . . . . ?
C9 C14 C15 C5 179.8(7) . . . . ?
C8 C14 C15 C12 176.9(7) . . . . ?
C9 C14 C15 C12 -1.4(11) . . . . ?
C6 C5 C15 C14 2.5(10) . . . . ?
C4 C5 C15 C14 -178.0(6) . . . . ?
C6 C5 C15 C12 -176.3(6) . . . . ?
C4 C5 C15 C12 3.2(8) . . . . ?
C11 C12 C15 C14 0.5(11) . . . . ?
C13 C12 C15 C14 178.8(6) . . . . ?
C11 C12 C15 C5 179.4(7) . . . . ?
C13 C12 C15 C5 -2.4(8) . . . . ?
C4 N1 C16 C21 -67.6(9) . . . . ?
Mn1 N1 C16 C21 108.3(7) . . . . ?
C4 N1 C16 C17 112.5(8) . . . . ?
Mn1 N1 C16 C17 -71.6(8) . . . . ?
C21 C16 C17 C18 1.8(12) . . . . ?
N1 C16 C17 C18 -178.3(7) . . . . ?
C16 C17 C18 C19 0.2(14) . . . . ?
C17 C18 C19 C20 -2.3(14) . . . . ?
C17 C18 C19 Cl2 179.1(7) . . . . ?
C18 C19 C20 C21 2.3(14) . . . . ?
Cl2 C19 C20 C21 -179.1(7) . . . . ?
C19 C20 C21 C16 -0.2(13) . . . . ?
C17 C16 C21 C20 -1.8(12) . . . . ?
N1 C16 C21 C20 178.3(7) . . . . ?
C13 N2 C22 C23 102.1(9) . . . . ?
Mn1 N2 C22 C23 -83.4(9) . . . . ?
C13 N2 C22 C27 -76.8(9) . . . . ?
Mn1 N2 C22 C27 97.6(7) . . . . ?
C27 C22 C23 C24 3.0(14) . . . . ?
N2 C22 C23 C24 -175.9(9) . . . . ?
C22 C23 C24 C25 -1.6(16) . . . . ?
C23 C24 C25 C26 -1.9(16) . . . . ?
C23 C24 C25 Cl1 177.6(8) . . . . ?
C24 C25 C26 C27 3.8(14) . . . . ?
Cl1 C25 C26 C27 -175.6(7) . . . . ?
C23 C22 C27 C26 -1.0(13) . . . . ?
N2 C22 C27 C26 177.9(7) . . . . ?
C25 C26 C27 C22 -2.4(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        24.11
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.545
_refine_diff_density_min         -1.073
_refine_diff_density_rms         0.114


_chemical_properties_physical    'Light-sensitive, Photo-sensitive'
