# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_d:\determination\solution\c359\khc359-abs1
_database_code_depnum_ccdc_archive 'CCDC 1016022'
_audit_update_record             
;
2014-07-25 deposited with the CCDC.
2015-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 Cl2 I2 Mn1 N4 O2'
_chemical_formula_weight         774.06

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'
I I -0.4742 1.8119 '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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn

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

_cell_length_a                   13.3390(12)
_cell_length_b                   9.4207(7)
_cell_length_c                   20.8663(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2622.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    12193
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      26.00

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.961
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1484
_exptl_absorpt_coefficient_mu    3.092
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.4017
_exptl_absorpt_correction_T_max  0.5219
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12193
_diffrn_reflns_av_R_equivalents  0.0700
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2588
_reflns_number_gt                1977
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0334P)²+1.2975P] 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     SHELXL
_refine_ls_extinction_coef       0.00103(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2588
_refine_ls_number_parameters     160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.0827
_refine_ls_wR_factor_gt          0.0774
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001

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
C1 C 0.2110(3) 0.4761(5) 0.3211(2) 0.0344(10) Uani 1 1 d . . .
H1 H 0.1710 0.5377 0.3448 0.041 Uiso 1 1 calc R . .
C2 C 0.3122(3) 0.4762(5) 0.3321(3) 0.0434(12) Uani 1 1 d . . .
H2 H 0.3402 0.5367 0.3624 0.052 Uiso 1 1 calc R . .
C3 C 0.3712(4) 0.3852(6) 0.2975(3) 0.0528(14) Uani 1 1 d . . .
H3 H 0.4400 0.3818 0.3044 0.063 Uiso 1 1 calc R . .
C4 C 0.3274(4) 0.2986(4) 0.2520(3) 0.0422(12) Uani 1 1 d . . .
H4 H 0.3664 0.2371 0.2276 0.051 Uiso 1 1 calc R . .
C5 C 0.2256(3) 0.3044(4) 0.2435(2) 0.0272(9) Uani 1 1 d . . .
C6 C 0.1671(3) 0.2137(4) 0.1975(2) 0.0281(9) Uani 1 1 d . . .
C7 C 0.1812(3) 0.0288(4) 0.1130(2) 0.0312(10) Uani 1 1 d . . .
C8 C 0.0797(4) -0.0015(5) 0.1060(2) 0.0407(11) Uani 1 1 d . . .
H8 H 0.0322 0.0453 0.1310 0.049 Uiso 1 1 calc R . .
C9 C 0.0501(4) -0.1014(5) 0.0617(3) 0.0438(12) Uani 1 1 d . . .
H9 H -0.0177 -0.1231 0.0579 0.053 Uiso 1 1 calc R . .
C10 C 0.1174(4) -0.1690(5) 0.0234(2) 0.0393(11) Uani 1 1 d . . .
C11 C 0.2178(4) -0.1395(5) 0.0296(3) 0.0503(14) Uani 1 1 d . . .
H11 H 0.2644 -0.1862 0.0040 0.060 Uiso 1 1 calc R . .
C12 C 0.2495(4) -0.0394(5) 0.0744(3) 0.0462(12) Uani 1 1 d . . .
H12 H 0.3174 -0.0186 0.0782 0.055 Uiso 1 1 calc R . .
N1 N 0.1670(3) 0.3922(3) 0.27823(18) 0.0290(8) Uani 1 1 d . . .
N2 N 0.2188(3) 0.1259(3) 0.15914(18) 0.0312(8) Uani 1 1 d . . .
H2B H 0.2830 0.1288 0.1629 0.037 Uiso 1 1 calc R . .
O1 O 0.0747(2) 0.2209(3) 0.19764(17) 0.0375(7) Uani 1 1 d . . .
Mn1 Mn 0.0000 0.39839(9) 0.2500 0.0282(2) Uani 1 2 d S . .
I1 I 0.06748(3) -0.31948(3) -0.043535(18) 0.05515(15) Uani 1 1 d . . .
Cl1 Cl 0.03085(8) 0.56213(11) 0.15991(6) 0.0367(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
C1 N1 1.331(6) . ?
C1 C2 1.369(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.369(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(6) . ?
C4 H4 0.9300 . ?
C5 N1 1.349(5) . ?
C5 C6 1.505(6) . ?
C6 O1 1.234(5) . ?
C6 N2 1.342(5) . ?
C7 C12 1.376(6) . ?
C7 C8 1.392(7) . ?
C7 N2 1.420(5) . ?
C8 C9 1.378(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.360(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.375(7) . ?
C10 I1 2.099(4) . ?
C11 C12 1.395(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
N1 Mn1 2.304(3) . ?
N2 H2B 0.8600 . ?
O1 Mn1 2.230(3) . ?
Mn1 O1 2.233(3) 4 ?
Mn1 N1 2.305(3) 4 ?
Mn1 Cl1 2.4657(13) 4 ?
Mn1 Cl1 2.4669(13) . ?

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 C1 C2 123.4(4) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C1 C2 C3 118.4(5) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C2 C3 C4 119.3(5) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 119.0(4) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
N1 C5 C4 121.9(4) . . ?
N1 C5 C6 112.9(4) . . ?
C4 C5 C6 125.1(4) . . ?
O1 C6 N2 123.2(4) . . ?
O1 C6 C5 119.2(4) . . ?
N2 C6 C5 117.6(4) . . ?
C12 C7 C8 119.1(4) . . ?
C12 C7 N2 117.6(4) . . ?
C8 C7 N2 123.3(4) . . ?
C9 C8 C7 119.4(4) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C10 C9 C8 121.7(5) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C11 119.5(4) . . ?
C9 C10 I1 119.8(4) . . ?
C11 C10 I1 120.6(4) . . ?
C10 C11 C12 119.8(5) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C7 C12 C11 120.5(5) . . ?
C7 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C1 N1 C5 117.9(4) . . ?
C1 N1 Mn1 125.8(3) . . ?
C5 N1 Mn1 116.0(3) . . ?
C6 N2 C7 128.3(4) . . ?
C6 N2 H2B 115.9 . . ?
C7 N2 H2B 115.9 . . ?
C6 O1 Mn1 119.1(3) . . ?
O1 Mn1 O1 82.98(17) . 4 ?
O1 Mn1 N1 71.11(12) . . ?
O1 Mn1 N1 106.79(12) 4 . ?
O1 Mn1 N1 106.62(12) . 4 ?
O1 Mn1 N1 70.95(12) 4 4 ?
N1 Mn1 N1 177.12(16) . 4 ?
O1 Mn1 Cl1 156.37(9) . 4 ?
O1 Mn1 Cl1 91.22(9) 4 4 ?
N1 Mn1 Cl1 88.90(9) . 4 ?
N1 Mn1 Cl1 92.90(9) 4 4 ?
O1 Mn1 Cl1 91.18(9) . . ?
O1 Mn1 Cl1 156.37(9) 4 . ?
N1 Mn1 Cl1 92.75(9) . . ?
N1 Mn1 Cl1 89.05(9) 4 . ?
Cl1 Mn1 Cl1 102.57(6) 4 . ?

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
N1 C1 C2 C3 -0.2(8) . . . . ?
C1 C2 C3 C4 1.1(9) . . . . ?
C2 C3 C4 C5 -1.0(8) . . . . ?
C3 C4 C5 N1 0.0(7) . . . . ?
C3 C4 C5 C6 -178.1(5) . . . . ?
N1 C5 C6 O1 -3.8(6) . . . . ?
C4 C5 C6 O1 174.5(5) . . . . ?
N1 C5 C6 N2 177.8(4) . . . . ?
C4 C5 C6 N2 -4.0(7) . . . . ?
C12 C7 C8 C9 1.6(7) . . . . ?
N2 C7 C8 C9 -177.4(4) . . . . ?
C7 C8 C9 C10 -1.6(8) . . . . ?
C8 C9 C10 C11 1.3(8) . . . . ?
C8 C9 C10 I1 -179.7(4) . . . . ?
C9 C10 C11 C12 -0.8(8) . . . . ?
I1 C10 C11 C12 -179.9(4) . . . . ?
C8 C7 C12 C11 -1.2(8) . . . . ?
N2 C7 C12 C11 177.9(5) . . . . ?
C10 C11 C12 C7 0.8(8) . . . . ?
C2 C1 N1 C5 -0.8(7) . . . . ?
C2 C1 N1 Mn1 -174.2(4) . . . . ?
C4 C5 N1 C1 0.9(6) . . . . ?
C6 C5 N1 C1 179.2(4) . . . . ?
C4 C5 N1 Mn1 174.9(4) . . . . ?
C6 C5 N1 Mn1 -6.8(4) . . . . ?
O1 C6 N2 C7 0.3(7) . . . . ?
C5 C6 N2 C7 178.7(4) . . . . ?
C12 C7 N2 C6 173.2(4) . . . . ?
C8 C7 N2 C6 -7.8(7) . . . . ?
N2 C6 O1 Mn1 -168.6(3) . . . . ?
C5 C6 O1 Mn1 13.0(5) . . . . ?
C6 O1 Mn1 O1 -122.5(4) . . . 4 ?
C6 O1 Mn1 N1 -12.1(3) . . . . ?
C6 O1 Mn1 N1 169.8(3) . . . 4 ?
C6 O1 Mn1 Cl1 -45.7(5) . . . 4 ?
C6 O1 Mn1 Cl1 80.4(3) . . . . ?
C1 N1 Mn1 O1 -177.0(4) . . . . ?
C5 N1 Mn1 O1 9.5(3) . . . . ?
C1 N1 Mn1 O1 -100.7(4) . . . 4 ?
C5 N1 Mn1 O1 85.7(3) . . . 4 ?
C1 N1 Mn1 N1 -138.6(4) . . . 4 ?
C5 N1 Mn1 N1 47.9(3) . . . 4 ?
C1 N1 Mn1 Cl1 -9.8(4) . . . 4 ?
C5 N1 Mn1 Cl1 176.7(3) . . . 4 ?
C1 N1 Mn1 Cl1 92.7(4) . . . . ?
C5 N1 Mn1 Cl1 -80.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.815
_refine_diff_density_rms         0.092
####################################################################### 
# 
# 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_d:\determination\solution\b34\new
_database_code_depnum_ccdc_archive 'CCDC 1016023'
_audit_update_record             
;
2014-07-25 deposited with the CCDC.
2015-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 Br2 Cl2 Mn1 N4 O2'
_chemical_formula_weight         680.06

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   20.474(9)
_cell_length_b                   13.357(5)
_cell_length_c                   9.346(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.06(4)
_cell_angle_gamma                90.00
_cell_volume                     2555.3(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    11843
_cell_measurement_theta_min      1.82
_cell_measurement_theta_max      29.36

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.768
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1340
_exptl_absorpt_coefficient_mu    3.883
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.5142
_exptl_absorpt_correction_T_max  0.6521
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(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  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11843
_diffrn_reflns_av_R_equivalents  0.0914
_diffrn_reflns_av_sigmaI/netI    0.0845
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         29.36
_reflns_number_total             6064
_reflns_number_gt                5750
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.1000P)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         6064
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0790
_refine_ls_wR_factor_ref         0.1941
_refine_ls_wR_factor_gt          0.1754
_refine_ls_goodness_of_fit_ref   0.863
_refine_ls_restrained_S_all      0.863
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8245(6) 0.2102(8) 0.0232(13) 0.044(3) Uani 1 1 d . . .
H1 H 0.8465 0.1708 -0.0423 0.053 Uiso 1 1 calc R . .
C2 C 0.8359(6) 0.3099(8) 0.0289(13) 0.047(3) Uani 1 1 d . . .
H2 H 0.8688 0.3375 -0.0259 0.056 Uiso 1 1 calc R . .
C3 C 0.8006(7) 0.3687(8) 0.1120(14) 0.053(3) Uani 1 1 d . . .
H3 H 0.8083 0.4373 0.1125 0.064 Uiso 1 1 calc R . .
C4 C 0.7505(7) 0.3280(8) 0.2014(12) 0.046(3) Uani 1 1 d . . .
H4 H 0.7243 0.3681 0.2582 0.055 Uiso 1 1 calc R . .
C5 C 0.7441(5) 0.2241(8) 0.1967(11) 0.035(3) Uani 1 1 d . . .
C6 C 0.6952(5) 0.1673(8) 0.2959(11) 0.035(2) Uani 1 1 d . . .
C7 C 0.6078(5) 0.1806(7) 0.4779(12) 0.038(2) Uani 1 1 d . . .
C8 C 0.6006(6) 0.0808(8) 0.5135(14) 0.050(3) Uani 1 1 d . . .
H8 H 0.6283 0.0340 0.4727 0.060 Uiso 1 1 calc R . .
C9 C 0.5561(6) 0.0494(10) 0.6034(18) 0.063(4) Uani 1 1 d . . .
H9 H 0.5504 -0.0189 0.6183 0.075 Uiso 1 1 calc R . .
C10 C 0.5182(5) 0.1168(10) 0.6749(12) 0.045(3) Uani 1 1 d . . .
C11 C 0.5231(7) 0.2179(11) 0.6444(17) 0.068(4) Uani 1 1 d . . .
H11 H 0.4960 0.2643 0.6877 0.081 Uiso 1 1 calc R . .
C12 C 0.5692(8) 0.2475(10) 0.5481(13) 0.058(4) Uani 1 1 d . . .
H12 H 0.5744 0.3155 0.5300 0.070 Uiso 1 1 calc R . .
C13 C 0.6768(6) -0.2098(8) 0.0237(13) 0.042(3) Uani 1 1 d . . .
H13 H 0.6549 -0.1699 -0.0430 0.051 Uiso 1 1 calc R . .
C14 C 0.6639(6) -0.3108(7) 0.0253(13) 0.048(3) Uani 1 1 d . . .
H14 H 0.6314 -0.3385 -0.0332 0.058 Uiso 1 1 calc R . .
C15 C 0.7013(8) -0.3699(9) 0.1179(16) 0.066(5) Uani 1 1 d . . .
H15 H 0.6941 -0.4385 0.1235 0.080 Uiso 1 1 calc R . .
C16 C 0.7487(6) -0.3258(9) 0.2000(13) 0.052(3) Uani 1 1 d . . .
H16 H 0.7762 -0.3649 0.2571 0.062 Uiso 1 1 calc R . .
C17 C 0.7557(5) -0.2261(7) 0.1991(11) 0.032(2) Uani 1 1 d . . .
C18 C 0.8041(5) -0.1674(7) 0.2911(11) 0.033(2) Uani 1 1 d . . .
C19 C 0.8907(5) -0.1801(8) 0.4721(12) 0.040(3) Uani 1 1 d . . .
C20 C 0.8981(6) -0.0804(8) 0.5010(15) 0.055(4) Uani 1 1 d . . .
H20 H 0.8744 -0.0333 0.4481 0.066 Uiso 1 1 calc R . .
C21 C 0.9418(6) -0.0488(8) 0.6117(13) 0.049(3) Uani 1 1 d . . .
H21 H 0.9433 0.0182 0.6388 0.059 Uiso 1 1 calc R . .
C22 C 0.9804(6) -0.1148(9) 0.6762(11) 0.043(3) Uani 1 1 d . . .
C23 C 0.9768(6) -0.2163(10) 0.6414(14) 0.052(3) Uani 1 1 d . . .
H23 H 1.0057 -0.2615 0.6841 0.063 Uiso 1 1 calc R . .
C24 C 0.9307(6) -0.2494(8) 0.5441(12) 0.041(3) Uani 1 1 d . . .
H24 H 0.9260 -0.3175 0.5261 0.049 Uiso 1 1 calc R . .
N1 N 0.7808(4) 0.1671(6) 0.1133(8) 0.034(2) Uani 1 1 d . . .
N2 N 0.6561(4) 0.2182(6) 0.3741(8) 0.033(2) Uani 1 1 d . . .
H2B H 0.6582 0.2822 0.3650 0.039 Uiso 1 1 calc R . .
N3 N 0.7203(4) -0.1661(6) 0.1155(10) 0.038(2) Uani 1 1 d . . .
N4 N 0.8448(5) -0.2183(6) 0.3741(11) 0.047(3) Uani 1 1 d . . .
H4B H 0.8428 -0.2825 0.3673 0.056 Uiso 1 1 calc R . .
O1 O 0.6963(4) 0.0748(5) 0.2845(8) 0.0451(19) Uani 1 1 d . . .
O2 O 0.8030(4) -0.0738(5) 0.2829(8) 0.048(2) Uani 1 1 d . . .
Mn1 Mn 0.75017(8) -0.00022(12) 0.10342(16) 0.0336(4) Uani 1 1 d . . .
Br1 Br 0.45746(7) 0.07114(12) 0.81542(16) 0.0708(5) Uani 1 1 d . . .
Br2 Br 1.04253(7) -0.07124(12) 0.81518(16) 0.0730(5) Uani 1 1 d . . .
Cl1 Cl 0.65783(13) 0.03243(19) -0.0609(3) 0.0416(7) Uani 1 1 d . . .
Cl2 Cl 0.84222(13) -0.03194(19) -0.0625(3) 0.0434(7) 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
C1 C2 1.353(15) . ?
C1 N1 1.367(15) . ?
C1 H1 0.9300 . ?
C2 C3 1.328(19) . ?
C2 H2 0.9300 . ?
C3 C4 1.442(19) . ?
C3 H3 0.9300 . ?
C4 C5 1.395(14) . ?
C4 H4 0.9300 . ?
C5 N1 1.332(14) . ?
C5 C6 1.572(16) . ?
C6 O1 1.241(12) . ?
C6 N2 1.287(13) . ?
C7 C12 1.367(18) . ?
C7 C8 1.383(15) . ?
C7 N2 1.486(14) . ?
C8 C9 1.32(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.37(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.384(19) . ?
C10 Br1 1.925(12) . ?
C11 C12 1.38(2) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 N3 1.357(12) . ?
C13 C14 1.374(14) . ?
C13 H13 0.9300 . ?
C14 C15 1.391(15) . ?
C14 H14 0.9300 . ?
C15 C16 1.359(15) . ?
C15 H15 0.9300 . ?
C16 C17 1.339(15) . ?
C16 H16 0.9300 . ?
C17 N3 1.326(11) . ?
C17 C18 1.519(13) . ?
C18 O2 1.253(11) . ?
C18 N4 1.316(11) . ?
C19 C20 1.367(15) . ?
C19 N4 1.397(12) . ?
C19 C24 1.398(14) . ?
C20 C21 1.420(13) . ?
C20 H20 0.9300 . ?
C21 C22 1.321(15) . ?
C21 H21 0.9300 . ?
C22 C23 1.396(17) . ?
C22 Br2 1.892(9) . ?
C23 C24 1.372(15) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
N1 Mn1 2.323(8) . ?
N2 H2B 0.8600 . ?
N3 Mn1 2.302(9) . ?
N4 H4B 0.8600 . ?
O1 Mn1 2.270(9) . ?
O2 Mn1 2.209(6) . ?
Mn1 Cl1 2.452(3) . ?
Mn1 Cl2 2.499(4) . ?

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 C1 N1 120.3(11) . . ?
C2 C1 H1 119.8 . . ?
N1 C1 H1 119.8 . . ?
C3 C2 C1 120.6(12) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 121.1(10) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 115.1(11) . . ?
C5 C4 H4 122.4 . . ?
C3 C4 H4 122.4 . . ?
N1 C5 C4 122.2(11) . . ?
N1 C5 C6 116.3(9) . . ?
C4 C5 C6 121.4(10) . . ?
O1 C6 N2 126.0(11) . . ?
O1 C6 C5 114.6(10) . . ?
N2 C6 C5 119.3(9) . . ?
C12 C7 C8 116.7(13) . . ?
C12 C7 N2 119.3(10) . . ?
C8 C7 N2 123.9(10) . . ?
C9 C8 C7 122.5(13) . . ?
C9 C8 H8 118.7 . . ?
C7 C8 H8 118.7 . . ?
C8 C9 C10 120.4(12) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C11 119.8(12) . . ?
C9 C10 Br1 120.2(10) . . ?
C11 C10 Br1 120.0(10) . . ?
C12 C11 C10 118.0(13) . . ?
C12 C11 H11 121.0 . . ?
C10 C11 H11 121.0 . . ?
C7 C12 C11 122.4(13) . . ?
C7 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
N3 C13 C14 122.6(9) . . ?
N3 C13 H13 118.7 . . ?
C14 C13 H13 118.7 . . ?
C13 C14 C15 117.4(9) . . ?
C13 C14 H14 121.3 . . ?
C15 C14 H14 121.3 . . ?
C16 C15 C14 119.0(11) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C17 C16 C15 120.2(10) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
N3 C17 C16 123.2(9) . . ?
N3 C17 C18 111.5(8) . . ?
C16 C17 C18 125.4(8) . . ?
O2 C18 N4 124.3(8) . . ?
O2 C18 C17 118.0(7) . . ?
N4 C18 C17 117.7(8) . . ?
C20 C19 N4 123.7(9) . . ?
C20 C19 C24 119.3(9) . . ?
N4 C19 C24 117.0(9) . . ?
C19 C20 C21 119.9(9) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C22 C21 C20 119.9(10) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C21 C22 C23 120.8(9) . . ?
C21 C22 Br2 119.8(9) . . ?
C23 C22 Br2 119.3(8) . . ?
C24 C23 C22 120.0(9) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C19 119.7(10) . . ?
C23 C24 H24 120.2 . . ?
C19 C24 H24 120.2 . . ?
C5 N1 C1 120.2(9) . . ?
C5 N1 Mn1 114.7(7) . . ?
C1 N1 Mn1 124.0(7) . . ?
C6 N2 C7 128.4(9) . . ?
C6 N2 H2B 115.8 . . ?
C7 N2 H2B 115.8 . . ?
C17 N3 C13 117.2(9) . . ?
C17 N3 Mn1 117.9(6) . . ?
C13 N3 Mn1 123.7(6) . . ?
C18 N4 C19 127.4(9) . . ?
C18 N4 H4B 116.3 . . ?
C19 N4 H4B 116.3 . . ?
C6 O1 Mn1 120.9(7) . . ?
C18 O2 Mn1 119.9(5) . . ?
O2 Mn1 O1 82.4(3) . . ?
O2 Mn1 N3 70.2(3) . . ?
O1 Mn1 N3 104.8(3) . . ?
O2 Mn1 N1 105.6(3) . . ?
O1 Mn1 N1 71.3(3) . . ?
N3 Mn1 N1 174.9(3) . . ?
O2 Mn1 Cl1 156.2(2) . . ?
O1 Mn1 Cl1 90.5(2) . . ?
N3 Mn1 Cl1 89.95(19) . . ?
N1 Mn1 Cl1 93.35(19) . . ?
O2 Mn1 Cl2 91.8(3) . . ?
O1 Mn1 Cl2 156.9(2) . . ?
N3 Mn1 Cl2 94.1(3) . . ?
N1 Mn1 Cl2 89.0(3) . . ?
Cl1 Mn1 Cl2 102.89(11) . . ?

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
N1 C1 C2 C3 -6.4(17) . . . . ?
C1 C2 C3 C4 1.8(18) . . . . ?
C2 C3 C4 C5 2.0(16) . . . . ?
C3 C4 C5 N1 -1.2(14) . . . . ?
C3 C4 C5 C6 175.6(8) . . . . ?
N1 C5 C6 O1 -0.3(10) . . . . ?
C4 C5 C6 O1 -177.3(9) . . . . ?
N1 C5 C6 N2 -176.7(7) . . . . ?
C4 C5 C6 N2 6.2(12) . . . . ?
C12 C7 C8 C9 4.5(16) . . . . ?
N2 C7 C8 C9 -178.2(10) . . . . ?
C7 C8 C9 C10 -5.5(18) . . . . ?
C8 C9 C10 C11 5.1(17) . . . . ?
C8 C9 C10 Br1 -175.7(9) . . . . ?
C9 C10 C11 C12 -3.7(18) . . . . ?
Br1 C10 C11 C12 177.1(9) . . . . ?
C8 C7 C12 C11 -3.2(16) . . . . ?
N2 C7 C12 C11 179.3(10) . . . . ?
C10 C11 C12 C7 3.0(19) . . . . ?
N3 C13 C14 C15 -5(2) . . . . ?
C13 C14 C15 C16 -1(2) . . . . ?
C14 C15 C16 C17 5(2) . . . . ?
C15 C16 C17 N3 -3(2) . . . . ?
C15 C16 C17 C18 176.7(13) . . . . ?
N3 C17 C18 O2 3.2(15) . . . . ?
C16 C17 C18 O2 -176.8(13) . . . . ?
N3 C17 C18 N4 -176.7(11) . . . . ?
C16 C17 C18 N4 3.3(18) . . . . ?
N4 C19 C20 C21 174.1(13) . . . . ?
C24 C19 C20 C21 -5(2) . . . . ?
C19 C20 C21 C22 7(2) . . . . ?
C20 C21 C22 C23 -2.8(19) . . . . ?
C20 C21 C22 Br2 176.0(11) . . . . ?
C21 C22 C23 C24 -3.2(19) . . . . ?
Br2 C22 C23 C24 178.0(10) . . . . ?
C22 C23 C24 C19 4.9(19) . . . . ?
C20 C19 C24 C23 -0.5(19) . . . . ?
N4 C19 C24 C23 179.9(12) . . . . ?
C4 C5 N1 C1 -3.2(13) . . . . ?
C6 C5 N1 C1 179.8(8) . . . . ?
C4 C5 N1 Mn1 -172.0(7) . . . . ?
C6 C5 N1 Mn1 11.0(8) . . . . ?
C2 C1 N1 C5 7.2(14) . . . . ?
C2 C1 N1 Mn1 174.9(8) . . . . ?
O1 C6 N2 C7 6.0(14) . . . . ?
C5 C6 N2 C7 -178.0(7) . . . . ?
C12 C7 N2 C6 -178.2(9) . . . . ?
C8 C7 N2 C6 4.6(14) . . . . ?
C16 C17 N3 C13 -2.5(17) . . . . ?
C18 C17 N3 C13 177.5(11) . . . . ?
C16 C17 N3 Mn1 -170.7(11) . . . . ?
C18 C17 N3 Mn1 9.3(12) . . . . ?
C14 C13 N3 C17 6.9(18) . . . . ?
C14 C13 N3 Mn1 174.3(11) . . . . ?
O2 C18 N4 C19 3.7(19) . . . . ?
C17 C18 N4 C19 -176.5(12) . . . . ?
C20 C19 N4 C18 3(2) . . . . ?
C24 C19 N4 C18 -177.2(13) . . . . ?
N2 C6 O1 Mn1 164.7(7) . . . . ?
C5 C6 O1 Mn1 -11.4(10) . . . . ?
N4 C18 O2 Mn1 164.9(9) . . . . ?
C17 C18 O2 Mn1 -14.9(14) . . . . ?
C18 O2 Mn1 O1 123.1(9) . . . . ?
C18 O2 Mn1 N3 14.4(9) . . . . ?
C18 O2 Mn1 N1 -168.7(9) . . . . ?
C18 O2 Mn1 Cl1 49.5(12) . . . . ?
C18 O2 Mn1 Cl2 -79.3(9) . . . . ?
C6 O1 Mn1 O2 122.4(7) . . . . ?
C6 O1 Mn1 N3 -170.5(7) . . . . ?
C6 O1 Mn1 N1 13.0(7) . . . . ?
C6 O1 Mn1 Cl1 -80.4(7) . . . . ?
C6 O1 Mn1 Cl2 45.7(10) . . . . ?
C17 N3 Mn1 O2 -12.3(8) . . . . ?
C13 N3 Mn1 O2 -179.7(10) . . . . ?
C17 N3 Mn1 O1 -88.4(8) . . . . ?
C13 N3 Mn1 O1 104.2(9) . . . . ?
C17 N3 Mn1 N1 -49(4) . . . . ?
C13 N3 Mn1 N1 144(3) . . . . ?
C17 N3 Mn1 Cl1 -178.9(8) . . . . ?
C13 N3 Mn1 Cl1 13.7(9) . . . . ?
C17 N3 Mn1 Cl2 78.2(8) . . . . ?
C13 N3 Mn1 Cl2 -89.2(9) . . . . ?
C5 N1 Mn1 O2 -88.1(6) . . . . ?
C1 N1 Mn1 O2 103.6(7) . . . . ?
C5 N1 Mn1 O1 -12.0(5) . . . . ?
C1 N1 Mn1 O1 179.7(8) . . . . ?
C5 N1 Mn1 N3 -53(4) . . . . ?
C1 N1 Mn1 N3 139(4) . . . . ?
C5 N1 Mn1 Cl1 77.4(6) . . . . ?
C1 N1 Mn1 Cl1 -90.9(7) . . . . ?
C5 N1 Mn1 Cl2 -179.7(6) . . . . ?
C1 N1 Mn1 Cl2 12.0(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        29.36
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.691
_refine_diff_density_min         -0.641
_refine_diff_density_rms         0.166
####################################################################### 
# 
# 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_d:\determination\solution\c575\khc575
_database_code_depnum_ccdc_archive 'CCDC 1016026'
_audit_update_record             
;
2014-07-25 deposited with the CCDC.
2015-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H9 Cl3 Mn1 N2 O1'
_chemical_formula_weight         358.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/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                   6.8043(8)
_cell_length_b                   12.7288(13)
_cell_length_c                   15.384(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.851(11)
_cell_angle_gamma                90.00
_cell_volume                     1327.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7099
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      27.00

_exptl_crystal_description       Needle
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.794
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             716
_exptl_absorpt_coefficient_mu    1.588
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8521
_exptl_absorpt_correction_T_max  0.9001
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(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  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7099
_diffrn_reflns_av_R_equivalents  0.0965
_diffrn_reflns_av_sigmaI/netI    0.1010
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.66
_diffrn_reflns_theta_max         27.00
_reflns_number_total             2889
_reflns_number_gt                2515
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0000P)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         2889
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0712
_refine_ls_wR_factor_ref         0.1009
_refine_ls_wR_factor_gt          0.0923
_refine_ls_goodness_of_fit_ref   0.914
_refine_ls_restrained_S_all      0.914
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5295(14) 0.7347(7) 0.9059(5) 0.034(2) Uani 1 1 d . . .
H1 H 0.5921 0.7211 0.9608 0.041 Uiso 1 1 calc R . .
C2 C 0.6169(14) 0.8056(7) 0.8550(5) 0.041(2) Uani 1 1 d . . .
H2 H 0.7341 0.8389 0.8745 0.049 Uiso 1 1 calc R . .
C3 C 0.5237(14) 0.8261(7) 0.7727(5) 0.041(2) Uani 1 1 d . . .
H3 H 0.5788 0.8731 0.7353 0.050 Uiso 1 1 calc R . .
C4 C 0.3492(12) 0.7762(7) 0.7474(5) 0.032(2) Uani 1 1 d . . .
H4 H 0.2831 0.7893 0.6931 0.039 Uiso 1 1 calc R . .
C5 C 0.2739(12) 0.7057(6) 0.8049(4) 0.0203(19) Uani 1 1 d . . .
C6 C 0.0915(13) 0.6407(6) 0.7825(4) 0.026(2) Uani 1 1 d . . .
C7 C -0.2163(11) 0.6281(7) 0.6865(4) 0.0233(18) Uani 1 1 d . . .
C8 C -0.3198(12) 0.5596(6) 0.7336(4) 0.028(2) Uani 1 1 d . . .
H8 H -0.2692 0.5396 0.7892 0.034 Uiso 1 1 calc R . .
C9 C -0.4958(12) 0.5204(7) 0.7001(4) 0.030(2) Uani 1 1 d . . .
H9 H -0.5638 0.4730 0.7325 0.036 Uiso 1 1 calc R . .
C10 C -0.5740(12) 0.5505(7) 0.6183(4) 0.034(2) Uani 1 1 d . . .
C11 C -0.4715(13) 0.6195(7) 0.5698(5) 0.035(2) Uani 1 1 d . . .
H11 H -0.5235 0.6399 0.5146 0.043 Uiso 1 1 calc R . .
C12 C -0.2926(12) 0.6579(7) 0.6034(5) 0.032(2) Uani 1 1 d . . .
H12 H -0.2223 0.7039 0.5706 0.039 Uiso 1 1 calc R . .
N1 N 0.3643(10) 0.6838(5) 0.8841(3) 0.0240(16) Uani 1 1 d . . .
N2 N -0.0352(10) 0.6749(5) 0.7186(4) 0.0309(18) Uani 1 1 d . . .
H2A H -0.0040 0.7322 0.6936 0.037 Uiso 1 1 calc R . .
O1 O 0.0716(8) 0.5596(4) 0.8232(3) 0.0316(14) Uani 1 1 d . . .
Mn1 Mn 0.23740(19) 0.54042(10) 0.95436(7) 0.0249(3) Uani 1 1 d . . .
Cl1 Cl -0.8069(3) 0.5092(2) 0.57689(13) 0.0538(8) Uani 1 1 d . . .
Cl2 Cl 0.0490(3) 0.37480(17) 0.98048(14) 0.0365(5) Uani 1 1 d . . .
Cl3 Cl 0.4747(3) 0.57906(16) 1.08875(11) 0.0270(5) 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
C1 N1 1.316(10) . ?
C1 C2 1.364(11) . ?
C1 H1 0.9300 . ?
C2 C3 1.392(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(10) . ?
C4 H4 0.9300 . ?
C5 N1 1.346(9) . ?
C5 C6 1.507(11) . ?
C6 O1 1.221(8) . ?
C6 N2 1.325(9) . ?
C7 C8 1.367(10) . ?
C7 C12 1.391(10) . ?
C7 N2 1.419(10) . ?
C8 C9 1.358(11) . ?
C8 H8 0.9300 . ?
C9 C10 1.379(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.379(10) . ?
C10 Cl1 1.738(8) . ?
C11 C12 1.372(11) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
N1 Mn1 2.324(7) . ?
N2 H2A 0.8600 . ?
O1 Mn1 2.241(5) . ?
Mn1 Cl2 2.509(3) 3_567 ?
Mn1 Cl2 2.517(3) . ?
Mn1 Cl3 2.561(2) . ?
Mn1 Cl3 2.610(2) 3_667 ?
Cl2 Mn1 2.510(3) 3_567 ?
Cl3 Mn1 2.610(2) 3_667 ?

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 C1 C2 125.8(8) . . ?
N1 C1 H1 117.1 . . ?
C2 C1 H1 117.1 . . ?
C1 C2 C3 117.3(9) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
C4 C3 C2 119.1(8) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 118.4(7) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
N1 C5 C4 123.1(8) . . ?
N1 C5 C6 113.5(7) . . ?
C4 C5 C6 123.3(7) . . ?
O1 C6 N2 124.4(8) . . ?
O1 C6 C5 118.2(7) . . ?
N2 C6 C5 117.5(7) . . ?
C8 C7 C12 119.5(8) . . ?
C8 C7 N2 123.7(7) . . ?
C12 C7 N2 116.8(7) . . ?
C9 C8 C7 120.7(7) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 120.2(7) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 119.8(8) . . ?
C11 C10 Cl1 118.8(6) . . ?
C9 C10 Cl1 121.3(7) . . ?
C12 C11 C10 119.8(7) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C7 119.9(7) . . ?
C11 C12 H12 120.0 . . ?
C7 C12 H12 120.0 . . ?
C1 N1 C5 116.3(7) . . ?
C1 N1 Mn1 127.7(5) . . ?
C5 N1 Mn1 115.1(5) . . ?
C6 N2 C7 127.7(7) . . ?
C6 N2 H2A 116.1 . . ?
C7 N2 H2A 116.1 . . ?
C6 O1 Mn1 119.0(5) . . ?
O1 Mn1 N1 71.0(2) . . ?
O1 Mn1 Cl2 87.94(14) . 3_567 ?
N1 Mn1 Cl2 100.36(17) . 3_567 ?
O1 Mn1 Cl2 90.59(15) . . ?
N1 Mn1 Cl2 161.09(16) . . ?
Cl2 Mn1 Cl2 82.72(8) 3_567 . ?
O1 Mn1 Cl3 160.28(15) . . ?
N1 Mn1 Cl3 89.49(16) . . ?
Cl2 Mn1 Cl3 93.02(8) 3_567 . ?
Cl2 Mn1 Cl3 109.07(8) . . ?
O1 Mn1 Cl3 99.56(14) . 3_667 ?
N1 Mn1 Cl3 91.31(17) . 3_667 ?
Cl2 Mn1 Cl3 167.72(7) 3_567 3_667 ?
Cl2 Mn1 Cl3 87.47(8) . 3_667 ?
Cl3 Mn1 Cl3 83.20(7) . 3_667 ?
Mn1 Cl2 Mn1 97.28(8) 3_567 . ?
Mn1 Cl3 Mn1 96.80(7) . 3_667 ?

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
N1 C1 C2 C3 0.0(14) . . . . ?
C1 C2 C3 C4 1.0(14) . . . . ?
C2 C3 C4 C5 -0.9(13) . . . . ?
C3 C4 C5 N1 -0.3(13) . . . . ?
C3 C4 C5 C6 -175.7(8) . . . . ?
N1 C5 C6 O1 -19.0(10) . . . . ?
C4 C5 C6 O1 156.8(8) . . . . ?
N1 C5 C6 N2 162.1(7) . . . . ?
C4 C5 C6 N2 -22.1(11) . . . . ?
C12 C7 C8 C9 0.1(12) . . . . ?
N2 C7 C8 C9 177.7(8) . . . . ?
C7 C8 C9 C10 -1.0(12) . . . . ?
C8 C9 C10 C11 1.1(12) . . . . ?
C8 C9 C10 Cl1 -175.3(6) . . . . ?
C9 C10 C11 C12 -0.2(12) . . . . ?
Cl1 C10 C11 C12 176.2(7) . . . . ?
C10 C11 C12 C7 -0.7(12) . . . . ?
C8 C7 C12 C11 0.8(12) . . . . ?
N2 C7 C12 C11 -177.0(8) . . . . ?
C2 C1 N1 C5 -1.1(13) . . . . ?
C2 C1 N1 Mn1 167.3(7) . . . . ?
C4 C5 N1 C1 1.2(12) . . . . ?
C6 C5 N1 C1 177.0(7) . . . . ?
C4 C5 N1 Mn1 -168.7(6) . . . . ?
C6 C5 N1 Mn1 7.1(8) . . . . ?
O1 C6 N2 C7 1.7(12) . . . . ?
C5 C6 N2 C7 -179.4(6) . . . . ?
C8 C7 N2 C6 22.1(12) . . . . ?
C12 C7 N2 C6 -160.2(8) . . . . ?
N2 C6 O1 Mn1 -159.6(5) . . . . ?
C5 C6 O1 Mn1 21.5(9) . . . . ?
C6 O1 Mn1 N1 -12.8(6) . . . . ?
C6 O1 Mn1 Cl2 88.9(6) . . . 3_567 ?
C6 O1 Mn1 Cl2 171.5(6) . . . . ?
C6 O1 Mn1 Cl3 -4.4(9) . . . . ?
C6 O1 Mn1 Cl3 -100.9(6) . . . 3_667 ?
C1 N1 Mn1 O1 -166.9(7) . . . . ?
C5 N1 Mn1 O1 1.6(5) . . . . ?
C1 N1 Mn1 Cl2 108.9(7) . . . 3_567 ?
C5 N1 Mn1 Cl2 -82.6(5) . . . 3_567 ?
C1 N1 Mn1 Cl2 -153.3(5) . . . . ?
C5 N1 Mn1 Cl2 15.2(10) . . . . ?
C1 N1 Mn1 Cl3 15.9(7) . . . . ?
C5 N1 Mn1 Cl3 -175.6(5) . . . . ?
C1 N1 Mn1 Cl3 -67.3(7) . . . 3_667 ?
C5 N1 Mn1 Cl3 101.3(5) . . . 3_667 ?
O1 Mn1 Cl2 Mn1 -87.85(15) . . . 3_567 ?
N1 Mn1 Cl2 Mn1 -100.7(5) . . . 3_567 ?
Cl2 Mn1 Cl2 Mn1 0.0 3_567 . . 3_567 ?
Cl3 Mn1 Cl2 Mn1 90.69(9) . . . 3_567 ?
Cl3 Mn1 Cl2 Mn1 172.60(8) 3_667 . . 3_567 ?
O1 Mn1 Cl3 Mn1 -99.4(4) . . . 3_667 ?
N1 Mn1 Cl3 Mn1 -91.38(17) . . . 3_667 ?
Cl2 Mn1 Cl3 Mn1 168.27(8) 3_567 . . 3_667 ?
Cl2 Mn1 Cl3 Mn1 84.93(9) . . . 3_667 ?
Cl3 Mn1 Cl3 Mn1 0.0 3_667 . . 3_667 ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.115
####################################################################### 
# 
# 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_d:\determination\solution\d146\new
_database_code_depnum_ccdc_archive 'CCDC 1016027'
_audit_update_record             
;
2014-07-25 deposited with the CCDC.
2015-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 Cl2 F2 Mn1 N4 O2'
_chemical_formula_weight         558.26

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Aba2

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

_cell_length_a                   13.476(4)
_cell_length_b                   19.011(4)
_cell_length_c                   9.349(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2394.9(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7297
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      28.00

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1132
_exptl_absorpt_coefficient_mu    0.820
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7301
_exptl_absorpt_correction_T_max  0.7852
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7297
_diffrn_reflns_av_R_equivalents  0.0985
_diffrn_reflns_av_sigmaI/netI    0.1131
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         27.99
_reflns_number_total             2885
_reflns_number_gt                1739
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0340P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_number_reflns         2885
_refine_ls_number_parameters     159
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.0894
_refine_ls_wR_factor_gt          0.0746
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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
C1 C 0.7954(3) -0.0853(2) 0.0224(5) 0.0478(9) Uani 1 1 d . . .
H1 H 0.8359 -0.1114 -0.0376 0.057 Uiso 1 1 calc R . .
C2 C 0.6945(3) -0.0983(2) 0.0215(5) 0.0550(11) Uani 1 1 d . . .
H2 H 0.6683 -0.1338 -0.0359 0.066 Uiso 1 1 calc R . .
C3 C 0.6338(3) -0.0590(2) 0.1051(5) 0.0595(12) Uani 1 1 d . . .
H3 H 0.5655 -0.0657 0.1031 0.071 Uiso 1 1 calc R . .
C4 C 0.6756(3) -0.0095(2) 0.1921(4) 0.0534(11) Uani 1 1 d . . .
H4 H 0.6360 0.0173 0.2524 0.064 Uiso 1 1 calc R . .
C5 C 0.7767(2) 0.0008(2) 0.1903(4) 0.0370(8) Uani 1 1 d . . .
C6 C 0.8333(2) 0.05307(19) 0.2791(4) 0.0374(8) Uani 1 1 d . . .
C7 C 0.8170(3) 0.14715(19) 0.4621(4) 0.0391(9) Uani 1 1 d . . .
C8 C 0.9149(3) 0.1702(2) 0.4637(5) 0.0625(13) Uani 1 1 d . . .
H8 H 0.9613 0.1502 0.4029 0.075 Uiso 1 1 calc R . .
C9 C 0.9421(3) 0.2228(3) 0.5562(5) 0.0749(16) Uani 1 1 d . . .
H9 H 1.0071 0.2392 0.5578 0.090 Uiso 1 1 calc R . .
C10 C 0.8744(4) 0.2507(2) 0.6447(5) 0.0639(12) Uani 1 1 d . . .
C11 C 0.7776(4) 0.2298(2) 0.6462(5) 0.0622(13) Uani 1 1 d . . .
H11 H 0.7325 0.2500 0.7088 0.075 Uiso 1 1 calc R . .
C12 C 0.7491(3) 0.17806(19) 0.5524(4) 0.0534(12) Uani 1 1 d . . .
H12 H 0.6832 0.1636 0.5495 0.064 Uiso 1 1 calc R . .
N1 N 0.83661(19) -0.03676(15) 0.1057(4) 0.0391(7) Uani 1 1 d . . .
N2 N 0.7810(2) 0.09363(15) 0.3696(3) 0.0415(8) Uani 1 1 d . . .
H2A H 0.7181 0.0862 0.3716 0.050 Uiso 1 1 calc R . .
O1 O 0.92455(18) 0.05730(14) 0.2670(3) 0.0503(7) Uani 1 1 d . . .
F1 F 0.9026(2) 0.30182(16) 0.7385(4) 0.0987(10) Uani 1 1 d . . .
Mn1 Mn 1.0000 0.0000 0.09039(9) 0.03940(19) Uani 1 2 d S . .
Cl1 Cl 0.96484(7) 0.09555(5) -0.08011(11) 0.0498(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
C1 N1 1.326(5) . ?
C1 C2 1.382(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.359(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.363(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(5) . ?
C4 H4 0.9300 . ?
C5 N1 1.340(4) . ?
C5 C6 1.500(5) . ?
C6 O1 1.239(4) . ?
C6 N2 1.347(4) . ?
C7 C12 1.381(5) . ?
C7 C8 1.389(5) . ?
C7 N2 1.419(4) . ?
C8 C9 1.371(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.344(6) . ?
C9 H9 0.9300 . ?
C10 F1 1.361(5) . ?
C10 C11 1.364(7) . ?
C11 C12 1.372(6) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
N1 Mn1 2.315(3) . ?
N2 H2A 0.8600 . ?
O1 Mn1 2.224(3) . ?
Mn1 O1 2.224(3) 2_755 ?
Mn1 N1 2.314(3) 2_755 ?
Mn1 Cl1 2.4627(14) . ?
Mn1 Cl1 2.4627(14) 2_755 ?

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 C1 C2 122.5(4) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C3 C2 C1 119.6(4) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 118.4(3) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C3 C4 C5 119.7(4) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 122.2(3) . . ?
N1 C5 C6 111.9(3) . . ?
C4 C5 C6 125.9(3) . . ?
O1 C6 N2 123.0(3) . . ?
O1 C6 C5 119.6(3) . . ?
N2 C6 C5 117.5(3) . . ?
C12 C7 C8 119.5(4) . . ?
C12 C7 N2 116.9(3) . . ?
C8 C7 N2 123.6(3) . . ?
C9 C8 C7 119.1(4) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C10 C9 C8 119.7(4) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 F1 119.4(4) . . ?
C9 C10 C11 123.0(4) . . ?
F1 C10 C11 117.6(5) . . ?
C10 C11 C12 117.8(4) . . ?
C10 C11 H11 121.1 . . ?
C12 C11 H11 121.1 . . ?
C11 C12 C7 120.8(4) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C1 N1 C5 117.7(3) . . ?
C1 N1 Mn1 124.6(3) . . ?
C5 N1 Mn1 116.9(2) . . ?
C6 N2 C7 128.0(3) . . ?
C6 N2 H2A 116.0 . . ?
C7 N2 H2A 116.0 . . ?
C6 O1 Mn1 119.6(2) . . ?
O1 Mn1 O1 84.12(15) 2_755 . ?
O1 Mn1 N1 70.55(11) 2_755 2_755 ?
O1 Mn1 N1 103.95(11) . 2_755 ?
O1 Mn1 N1 103.95(11) 2_755 . ?
O1 Mn1 N1 70.55(11) . . ?
N1 Mn1 N1 172.93(17) 2_755 . ?
O1 Mn1 Cl1 158.38(7) 2_755 . ?
O1 Mn1 Cl1 91.86(8) . . ?
N1 Mn1 Cl1 90.02(8) 2_755 . ?
N1 Mn1 Cl1 94.57(8) . . ?
O1 Mn1 Cl1 91.74(8) 2_755 2_755 ?
O1 Mn1 Cl1 158.40(7) . 2_755 ?
N1 Mn1 Cl1 94.57(8) 2_755 2_755 ?
N1 Mn1 Cl1 90.02(8) . 2_755 ?
Cl1 Mn1 Cl1 99.33(6) . 2_755 ?

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
N1 C1 C2 C3 2.1(7) . . . . ?
C1 C2 C3 C4 -2.7(7) . . . . ?
C2 C3 C4 C5 1.8(7) . . . . ?
C3 C4 C5 N1 -0.3(7) . . . . ?
C3 C4 C5 C6 179.9(4) . . . . ?
N1 C5 C6 O1 0.5(5) . . . . ?
C4 C5 C6 O1 -179.7(4) . . . . ?
N1 C5 C6 N2 -179.4(3) . . . . ?
C4 C5 C6 N2 0.3(6) . . . . ?
C12 C7 C8 C9 0.6(6) . . . . ?
N2 C7 C8 C9 179.3(4) . . . . ?
C7 C8 C9 C10 0.7(7) . . . . ?
C8 C9 C10 F1 178.5(4) . . . . ?
C8 C9 C10 C11 -1.0(8) . . . . ?
C9 C10 C11 C12 -0.1(7) . . . . ?
F1 C10 C11 C12 -179.6(4) . . . . ?
C10 C11 C12 C7 1.5(6) . . . . ?
C8 C7 C12 C11 -1.8(6) . . . . ?
N2 C7 C12 C11 179.4(3) . . . . ?
C2 C1 N1 C5 -0.6(6) . . . . ?
C2 C1 N1 Mn1 -170.5(3) . . . . ?
C4 C5 N1 C1 -0.3(6) . . . . ?
C6 C5 N1 C1 179.5(3) . . . . ?
C4 C5 N1 Mn1 170.4(3) . . . . ?
C6 C5 N1 Mn1 -9.9(4) . . . . ?
O1 C6 N2 C7 1.2(6) . . . . ?
C5 C6 N2 C7 -178.8(3) . . . . ?
C12 C7 N2 C6 -175.6(4) . . . . ?
C8 C7 N2 C6 5.7(6) . . . . ?
N2 C6 O1 Mn1 -170.3(2) . . . . ?
C5 C6 O1 Mn1 9.7(4) . . . . ?
C6 O1 Mn1 O1 -117.6(3) . . . 2_755 ?
C6 O1 Mn1 N1 173.9(3) . . . 2_755 ?
C6 O1 Mn1 N1 -10.8(3) . . . . ?
C6 O1 Mn1 Cl1 83.7(3) . . . . ?
C6 O1 Mn1 Cl1 -37.8(4) . . . 2_755 ?
C1 N1 Mn1 O1 -100.7(3) . . . 2_755 ?
C5 N1 Mn1 O1 89.3(3) . . . 2_755 ?
C1 N1 Mn1 O1 -179.2(3) . . . . ?
C5 N1 Mn1 O1 10.8(3) . . . . ?
C1 N1 Mn1 Cl1 90.5(3) . . . . ?
C5 N1 Mn1 Cl1 -79.4(3) . . . . ?
C1 N1 Mn1 Cl1 -8.9(3) . . . 2_755 ?
C5 N1 Mn1 Cl1 -178.8(3) . . . 2_755 ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.052
