# 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_1
_database_code_depnum_ccdc_archive 'CCDC 972354'
_audit_update_record             
;
2013-11-17 deposited with the CCDC.
2015-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H104 Br5 Cl11 Co4 N8'
_chemical_formula_weight         1818.61

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'
Cl Cl 0.1484 0.1585 '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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P2(1)2(1)2(1) '

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

_cell_length_a                   10.0792(7)
_cell_length_b                   13.0655(9)
_cell_length_c                   13.5796(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1788.3(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8520
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      27.25

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             918
_exptl_absorpt_coefficient_mu    4.153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3688
_exptl_absorpt_correction_T_max  0.4905
_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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13624
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_sigmaI/netI    0.0164
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         25.67
_reflns_number_total             3389
_reflns_number_gt                3291
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0585P)²+9.1874P] 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   0.505(16)
_refine_ls_number_reflns         3389
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1119
_refine_ls_wR_factor_gt          0.1076
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1423(7) 0.5310(5) 0.4871(5) 0.0282(15) Uani 1 1 d . . .
H1A H 0.1587 0.4746 0.4434 0.042 Uiso 1 1 calc R . .
H1B H 0.0590 0.5623 0.4706 0.042 Uiso 1 1 calc R . .
H1C H 0.1393 0.5066 0.5538 0.042 Uiso 1 1 calc R . .
C2 C 0.3869(6) 0.5573(6) 0.4856(5) 0.0280(14) Uani 1 1 d . . .
H2A H 0.3966 0.5290 0.5504 0.042 Uiso 1 1 calc R . .
H2B H 0.4558 0.6068 0.4743 0.042 Uiso 1 1 calc R . .
H2C H 0.3935 0.5036 0.4376 0.042 Uiso 1 1 calc R . .
C3 C 0.2525(6) 0.6090(4) 0.4769(4) 0.0192(11) Uani 1 1 d . . .
H3 H 0.2442 0.6580 0.5312 0.023 Uiso 1 1 calc R . .
C4 C 0.2256(6) 0.6002(4) 0.2903(4) 0.0141(10) Uani 1 1 d . . .
H4A H 0.1381 0.5693 0.2898 0.017 Uiso 1 1 calc R . .
H4B H 0.2911 0.5459 0.2931 0.017 Uiso 1 1 calc R . .
C5 C 0.1206(5) 0.7387(4) 0.3813(4) 0.0139(11) Uani 1 1 d . . .
H5A H 0.1367 0.7948 0.4266 0.017 Uiso 1 1 calc R . .
H5B H 0.0439 0.7009 0.4046 0.017 Uiso 1 1 calc R . .
C6 C 0.3609(5) 0.7366(4) 0.3629(4) 0.0142(11) Uani 1 1 d . . .
H6A H 0.3844 0.7705 0.4240 0.017 Uiso 1 1 calc R . .
H6B H 0.4356 0.6952 0.3421 0.017 Uiso 1 1 calc R . .
C7 C 0.0929(5) 0.7811(4) 0.2783(4) 0.0150(11) Uani 1 1 d . . .
H7A H 0.0240 0.7411 0.2466 0.018 Uiso 1 1 calc R . .
H7B H 0.0627 0.8514 0.2829 0.018 Uiso 1 1 calc R . .
C8 C 0.2459(6) 0.6646(4) 0.1963(3) 0.0129(10) Uani 1 1 d . . .
H8A H 0.3362 0.6566 0.1728 0.016 Uiso 1 1 calc R . .
H8B H 0.1861 0.6411 0.1451 0.016 Uiso 1 1 calc R . .
C9 C 0.3291(6) 0.8158(4) 0.2846(4) 0.0172(11) Uani 1 1 d . . .
H9A H 0.3014 0.8791 0.3156 0.021 Uiso 1 1 calc R . .
H9B H 0.4076 0.8296 0.2456 0.021 Uiso 1 1 calc R . .
C10 C 0.2097(6) 0.8416(5) 0.1251(4) 0.0225(13) Uani 1 1 d . . .
H10 H 0.2080 0.9135 0.1456 0.027 Uiso 1 1 calc R . .
C11 C 0.3298(7) 0.8271(6) 0.0591(5) 0.0316(15) Uani 1 1 d . . .
H11A H 0.3279 0.7596 0.0310 0.047 Uiso 1 1 calc R . .
H11B H 0.4093 0.8353 0.0972 0.047 Uiso 1 1 calc R . .
H11C H 0.3281 0.8771 0.0073 0.047 Uiso 1 1 calc R . .
C12 C 0.0812(7) 0.8202(5) 0.0689(5) 0.0287(14) Uani 1 1 d . . .
H12A H 0.0763 0.8642 0.0124 0.043 Uiso 1 1 calc R . .
H12B H 0.0066 0.8330 0.1111 0.043 Uiso 1 1 calc R . .
H12C H 0.0799 0.7501 0.0479 0.043 Uiso 1 1 calc R . .
Cl1 Cl 0.05343(12) 0.94041(10) 0.79121(10) 0.0157(3) Uani 1 1 d . A .
Cl2 Cl 0.41355(10) 0.94227(8) 0.81903(8) 0.0049(2) Uani 1 1 d . A .
Br3 Br 0.22394(7) 0.67920(4) 0.76988(6) 0.0333(2) Uani 1 1 d . A .
Cl4 Cl 0.2784(10) 0.8853(8) 0.5741(8) 0.019(3) Uani 0.75 1 d P A 1
Br4 Br 0.2748(14) 0.8872(9) 0.5726(10) 0.019(3) Uani 0.25 1 d P A 2
Co1 Co 0.24122(7) 0.85935(5) 0.74103(5) 0.01280(18) Uani 1 1 d . . .
N1 N 0.2399(5) 0.6692(3) 0.3787(3) 0.0125(9) Uani 1 1 d . . .
N2 N 0.2191(4) 0.7759(3) 0.2188(3) 0.0124(8) 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 C3 1.514(8) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.519(8) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 N1 1.553(6) . ?
C3 H3 0.9800 . ?
C4 N1 1.508(6) . ?
C4 C8 1.542(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 N1 1.507(7) . ?
C5 C7 1.530(8) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C9 1.517(8) . ?
C6 N1 1.520(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N2 1.510(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N2 1.510(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N2 1.516(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.518(9) . ?
C10 C12 1.530(9) . ?
C10 N2 1.536(7) . ?
C10 H10 0.9800 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
Cl1 Co1 2.2734(14) . ?
Cl2 Co1 2.3048(12) . ?
Br3 Co1 2.3926(8) . ?
Cl4 Co1 2.323(12) . ?
Br4 Co1 2.341(14) . ?

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
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 C2 110.4(5) . . ?
C1 C3 N1 111.1(5) . . ?
C2 C3 N1 111.4(5) . . ?
C1 C3 H3 107.9 . . ?
C2 C3 H3 107.9 . . ?
N1 C3 H3 107.9 . . ?
N1 C4 C8 108.7(4) . . ?
N1 C4 H4A 110.0 . . ?
C8 C4 H4A 110.0 . . ?
N1 C4 H4B 110.0 . . ?
C8 C4 H4B 110.0 . . ?
H4A C4 H4B 108.3 . . ?
N1 C5 C7 110.0(4) . . ?
N1 C5 H5A 109.7 . . ?
C7 C5 H5A 109.7 . . ?
N1 C5 H5B 109.7 . . ?
C7 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
C9 C6 N1 108.9(4) . . ?
C9 C6 H6A 109.9 . . ?
N1 C6 H6A 109.9 . . ?
C9 C6 H6B 109.9 . . ?
N1 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
N2 C7 C5 108.7(4) . . ?
N2 C7 H7A 110.0 . . ?
C5 C7 H7A 110.0 . . ?
N2 C7 H7B 110.0 . . ?
C5 C7 H7B 110.0 . . ?
H7A C7 H7B 108.3 . . ?
N2 C8 C4 109.5(4) . . ?
N2 C8 H8A 109.8 . . ?
C4 C8 H8A 109.8 . . ?
N2 C8 H8B 109.8 . . ?
C4 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
N2 C9 C6 109.5(4) . . ?
N2 C9 H9A 109.8 . . ?
C6 C9 H9A 109.8 . . ?
N2 C9 H9B 109.8 . . ?
C6 C9 H9B 109.8 . . ?
H9A C9 H9B 108.2 . . ?
C11 C10 C12 110.9(5) . . ?
C11 C10 N2 111.7(5) . . ?
C12 C10 N2 111.3(5) . . ?
C11 C10 H10 107.5 . . ?
C12 C10 H10 107.5 . . ?
N2 C10 H10 107.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
Cl1 Co1 Cl2 105.71(5) . . ?
Cl1 Co1 Cl4 111.0(3) . . ?
Cl2 Co1 Cl4 105.0(3) . . ?
Cl1 Co1 Br4 109.9(3) . . ?
Cl2 Co1 Br4 105.5(3) . . ?
Cl4 Co1 Br4 1.1(6) . . ?
Cl1 Co1 Br3 110.40(5) . . ?
Cl2 Co1 Br3 116.23(4) . . ?
Cl4 Co1 Br3 108.4(3) . . ?
Br4 Co1 Br3 108.9(3) . . ?
C5 N1 C4 107.6(4) . . ?
C5 N1 C6 107.1(4) . . ?
C4 N1 C6 108.1(4) . . ?
C5 N1 C3 110.5(4) . . ?
C4 N1 C3 112.9(4) . . ?
C6 N1 C3 110.4(4) . . ?
C8 N2 C7 107.6(4) . . ?
C8 N2 C9 108.6(4) . . ?
C7 N2 C9 106.5(4) . . ?
C8 N2 C10 112.4(4) . . ?
C7 N2 C10 111.5(4) . . ?
C9 N2 C10 110.0(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 C5 C7 N2 -22.7(6) . . . . ?
N1 C4 C8 N2 -22.2(6) . . . . ?
N1 C6 C9 N2 -24.6(6) . . . . ?
C7 C5 N1 C4 -45.0(5) . . . . ?
C7 C5 N1 C6 71.0(5) . . . . ?
C7 C5 N1 C3 -168.7(4) . . . . ?
C8 C4 N1 C5 70.5(5) . . . . ?
C8 C4 N1 C6 -44.8(5) . . . . ?
C8 C4 N1 C3 -167.2(4) . . . . ?
C9 C6 N1 C5 -43.3(5) . . . . ?
C9 C6 N1 C4 72.4(5) . . . . ?
C9 C6 N1 C3 -163.7(4) . . . . ?
C1 C3 N1 C5 69.4(6) . . . . ?
C2 C3 N1 C5 -167.1(5) . . . . ?
C1 C3 N1 C4 -51.2(6) . . . . ?
C2 C3 N1 C4 72.3(6) . . . . ?
C1 C3 N1 C6 -172.3(5) . . . . ?
C2 C3 N1 C6 -48.8(6) . . . . ?
C4 C8 N2 C7 -45.3(5) . . . . ?
C4 C8 N2 C9 69.6(5) . . . . ?
C4 C8 N2 C10 -168.4(4) . . . . ?
C5 C7 N2 C8 71.1(5) . . . . ?
C5 C7 N2 C9 -45.2(5) . . . . ?
C5 C7 N2 C10 -165.2(4) . . . . ?
C6 C9 N2 C8 -42.5(6) . . . . ?
C6 C9 N2 C7 73.1(5) . . . . ?
C6 C9 N2 C10 -165.9(4) . . . . ?
C11 C10 N2 C8 -52.5(7) . . . . ?
C12 C10 N2 C8 72.2(6) . . . . ?
C11 C10 N2 C7 -173.4(5) . . . . ?
C12 C10 N2 C7 -48.7(6) . . . . ?
C11 C10 N2 C9 68.7(6) . . . . ?
C12 C10 N2 C9 -166.7(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.67
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.276
_refine_diff_density_min         -1.406
_refine_diff_density_rms         0.132
####################################################################### 
# 
# 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_111
_database_code_depnum_ccdc_archive 'CCDC 972355'
_audit_update_record             
;
2013-11-17 deposited with the CCDC.
2015-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H104 Br5 Cl11 Co4 N8'
_chemical_formula_weight         1818.61

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 '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           Orthorhombic
_symmetry_space_group_name_H-M   'Pnma '

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

_cell_length_a                   13.7347(15)
_cell_length_b                   10.1454(11)
_cell_length_c                   13.1412(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1831.1(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             918
_exptl_absorpt_coefficient_mu    4.056
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3758
_exptl_absorpt_correction_T_max  0.4976
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13326
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0146
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         25.67
_reflns_number_total             1840
_reflns_number_gt                1516
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.2000P)²+0.4116P] 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         1840
_refine_ls_number_parameters     110
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0687
_refine_ls_wR_factor_ref         0.2653
_refine_ls_wR_factor_gt          0.2379
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_restrained_S_all      1.168
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5134(6) 0.1281(8) 0.2059(8) 0.090(3) Uani 1 1 d . . .
H1A H 0.5727 0.1119 0.2424 0.135 Uiso 1 1 calc R . .
H1B H 0.4992 0.0541 0.1629 0.135 Uiso 1 1 calc R . .
H1C H 0.4610 0.1407 0.2533 0.135 Uiso 1 1 calc R . .
C2 C 0.5249(6) 0.2500 0.1415(7) 0.055(2) Uani 1 2 d S . .
H2 H 0.4718 0.2500 0.0917 0.067 Uiso 1 2 calc SR . .
C3 C 0.6268(4) 0.1307(5) 0.0150(4) 0.0479(13) Uani 1 1 d . . .
H3A H 0.6238 0.0522 0.0569 0.057 Uiso 1 1 calc R . .
H3B H 0.5714 0.1297 -0.0307 0.057 Uiso 1 1 calc R . .
C4 C 0.7099(6) 0.2500 0.1477(5) 0.0475(19) Uani 1 2 d S . .
H4A H 0.7090 0.1726 0.1910 0.057 Uiso 0.50 1 calc PR . .
H4B H 0.7090 0.3274 0.1910 0.057 Uiso 0.50 1 calc PR . .
C5 C 0.7187(6) 0.1297(9) -0.0455(7) 0.077(2) Uani 1 1 d U . .
H5A H 0.7029 0.1260 -0.1175 0.092 Uiso 1 1 calc R . .
H5B H 0.7561 0.0516 -0.0287 0.092 Uiso 1 1 calc R . .
C6 C 0.8011(5) 0.2500 0.0847(5) 0.0422(16) Uani 1 2 d S . .
H6A H 0.8395 0.3273 0.1011 0.051 Uiso 0.50 1 calc PR . .
H6B H 0.8395 0.1727 0.1011 0.051 Uiso 0.50 1 calc PR . .
C7 C 0.8707(9) 0.2500 -0.0927(7) 0.075(3) Uani 1 2 d S . .
H7 H 0.8490 0.2500 -0.1638 0.090 Uiso 1 2 calc SR . .
C8 C 0.9306(6) 0.1283(10) -0.0765(8) 0.099(3) Uani 1 1 d . . .
H8A H 0.9904 0.1356 -0.1138 0.148 Uiso 1 1 calc R . .
H8B H 0.8950 0.0527 -0.1000 0.148 Uiso 1 1 calc R . .
H8C H 0.9446 0.1185 -0.0053 0.148 Uiso 1 1 calc R . .
Cl1 Cl 0.19101(11) 0.07182(11) 0.81344(10) 0.0499(5) Uani 1 1 d . A .
Br2 Br 0.23255(13) 0.2500 1.07308(9) 0.1002(6) Uani 1 2 d S A .
Cl3 Cl 0.4202(16) 0.2500 0.8737(16) 0.084(6) Uani 0.75 2 d SP A 1
Br3 Br 0.427(2) 0.2500 0.8576(19) 0.062(2) Uani 0.25 2 d SP A 2
Co1 Co 0.25718(8) 0.2500 0.89433(8) 0.0413(5) Uani 1 2 d S . .
N1 N 0.6217(5) 0.2500 0.0812(4) 0.0406(13) Uani 1 2 d S . .
N2 N 0.7788(5) 0.2500 -0.0248(5) 0.0467(15) Uani 1 2 d S . .


_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 1.506(9) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C1 1.506(9) 7_565 ?
C2 N1 1.548(10) . ?
C2 H2 0.9800 . ?
C3 C5 1.491(10) . ?
C3 N1 1.492(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N1 1.493(9) . ?
C4 C6 1.502(11) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 N2 1.498(9) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 N2 1.471(9) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.499(11) . ?
C7 C8 1.499(11) 7_565 ?
C7 N2 1.546(11) . ?
C7 H7 0.9800 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
Cl1 Co1 2.2855(13) . ?
Br2 Co1 2.3733(15) . ?
Cl3 Co1 2.26(2) . ?
Br3 Co1 2.39(3) . ?
Co1 Cl1 2.2855(13) 7_565 ?
N1 C3 1.492(6) 7_565 ?
N2 C5 1.498(9) 7_565 ?

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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 C1 110.4(9) 7_565 . ?
C1 C2 N1 112.2(5) 7_565 . ?
C1 C2 N1 112.2(5) . . ?
C1 C2 H2 107.3 7_565 . ?
C1 C2 H2 107.3 . . ?
N1 C2 H2 107.3 . . ?
C5 C3 N1 110.9(5) . . ?
C5 C3 H3A 109.5 . . ?
N1 C3 H3A 109.5 . . ?
C5 C3 H3B 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 108.0 . . ?
N1 C4 C6 110.8(6) . . ?
N1 C4 H4A 109.5 . . ?
C6 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
C6 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C3 C5 N2 111.3(6) . . ?
C3 C5 H5A 109.4 . . ?
N2 C5 H5A 109.4 . . ?
C3 C5 H5B 109.4 . . ?
N2 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
N2 C6 C4 111.4(6) . . ?
N2 C6 H6A 109.3 . . ?
C4 C6 H6A 109.3 . . ?
N2 C6 H6B 109.3 . . ?
C4 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C8 110.9(11) . 7_565 ?
C8 C7 N2 111.5(5) . . ?
C8 C7 N2 111.5(5) 7_565 . ?
C8 C7 H7 107.6 . . ?
C8 C7 H7 107.6 7_565 . ?
N2 C7 H7 107.6 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
Cl3 Co1 Cl1 109.8(3) . . ?
Cl3 Co1 Cl1 109.8(3) . 7_565 ?
Cl1 Co1 Cl1 104.55(8) . 7_565 ?
Cl3 Co1 Br2 105.1(5) . . ?
Cl1 Co1 Br2 113.81(5) . . ?
Cl1 Co1 Br2 113.81(5) 7_565 . ?
Cl3 Co1 Br3 4.8(11) . . ?
Cl1 Co1 Br3 107.2(3) . . ?
Cl1 Co1 Br3 107.2(3) 7_565 . ?
Br2 Co1 Br3 109.9(6) . . ?
C3 N1 C3 108.4(6) . 7_565 ?
C3 N1 C4 107.6(4) . . ?
C3 N1 C4 107.6(4) 7_565 . ?
C3 N1 C2 109.8(4) . . ?
C3 N1 C2 109.8(4) 7_565 . ?
C4 N1 C2 113.4(5) . . ?
C6 N2 C5 107.0(5) . . ?
C6 N2 C5 107.0(5) . 7_565 ?
C5 N2 C5 109.1(8) . 7_565 ?
C6 N2 C7 113.2(7) . . ?
C5 N2 C7 110.2(5) . . ?
C5 N2 C7 110.2(5) 7_565 . ?

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 C3 C5 N2 -1.3(8) . . . . ?
N1 C4 C6 N2 0.0 . . . . ?
C5 C3 N1 C3 58.9(8) . . . 7_565 ?
C5 C3 N1 C4 -57.2(7) . . . . ?
C5 C3 N1 C2 178.9(6) . . . . ?
C6 C4 N1 C3 58.3(4) . . . . ?
C6 C4 N1 C3 -58.3(4) . . . 7_565 ?
C6 C4 N1 C2 180.0 . . . . ?
C1 C2 N1 C3 -177.1(7) 7_565 . . . ?
C1 C2 N1 C3 58.0(9) . . . . ?
C1 C2 N1 C3 -58.0(9) 7_565 . . 7_565 ?
C1 C2 N1 C3 177.1(7) . . . 7_565 ?
C1 C2 N1 C4 62.4(7) 7_565 . . . ?
C1 C2 N1 C4 -62.4(7) . . . . ?
C4 C6 N2 C5 -58.4(5) . . . . ?
C4 C6 N2 C5 58.4(5) . . . 7_565 ?
C4 C6 N2 C7 180.0 . . . . ?
C3 C5 N2 C6 59.5(8) . . . . ?
C3 C5 N2 C5 -56.0(10) . . . 7_565 ?
C3 C5 N2 C7 -177.0(6) . . . . ?
C8 C7 N2 C6 62.3(7) . . . . ?
C8 C7 N2 C6 -62.3(7) 7_565 . . . ?
C8 C7 N2 C5 -57.5(10) . . . . ?
C8 C7 N2 C5 177.9(7) 7_565 . . . ?
C8 C7 N2 C5 -177.9(7) . . . 7_565 ?
C8 C7 N2 C5 57.5(10) 7_565 . . 7_565 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.67
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.573
_refine_diff_density_min         -2.674
_refine_diff_density_rms         0.164
####################################################################### 
# 
# 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_w290
_database_code_depnum_ccdc_archive 'CCDC 1026402'
_audit_update_record             
;
2014-09-26 deposited with the CCDC.
2015-01-13 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 H26 Br Cl3 Mn N2'
_chemical_formula_weight         439.55

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'
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           Orthorhombic
_symmetry_space_group_name_H-M   'Pnma '

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

_cell_length_a                   13.778(3)
_cell_length_b                   10.235(2)
_cell_length_c                   13.238(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1866.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5020
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      26.23
_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             892
_exptl_absorpt_coefficient_mu    3.267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3548
_exptl_absorpt_correction_T_max  0.5611
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13530
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0142
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         25.68
_reflns_number_total             1879
_reflns_number_gt                1554
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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         1879
_refine_ls_number_parameters     118
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1835
_refine_ls_wR_factor_gt          0.1677
_refine_ls_goodness_of_fit_ref   1.490
_refine_ls_restrained_S_all      1.521
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.24474(6) 0.7500 0.60550(6) 0.0452(3) Uani 1 2 d S . .
Cl2 Cl 0.31089(8) 0.93383(8) 0.68993(7) 0.0562(4) Uani 1 1 d . A .
Br1 Br 0.2729(2) 0.7500 0.42265(18) 0.1120(11) Uani 0.75 2 d SP A 1
Br3 Br 0.0690(8) 0.7500 0.6394(5) 0.068(2) Uani 0.25 2 d SP A 1
Cl1 Cl 0.2549(8) 0.7500 0.4200(13) 0.061(3) Uani 0.25 2 d SPU A 2
Cl3 Cl 0.0771(8) 0.7500 0.6300(6) 0.114(4) Uani 0.75 2 d SP A 2
C1 C 0.4306(4) 0.1294(7) 0.4229(5) 0.112(2) Uani 1 1 d . . .
H1A H 0.4592 0.1319 0.4890 0.168 Uiso 1 1 calc R . .
H1B H 0.4810 0.1250 0.3729 0.168 Uiso 1 1 calc R . .
H1C H 0.3897 0.0539 0.4173 0.168 Uiso 1 1 calc R . .
C2 C 0.3715(6) 0.2500 0.4067(5) 0.076(2) Uani 1 2 d S . .
H2 H 0.3504 0.2500 0.3360 0.091 Uiso 1 2 calc SR . .
C3 C 0.3022(4) 0.2500 0.5825(4) 0.0462(12) Uani 1 2 d S . .
H3A H 0.3406 0.3266 0.5987 0.055 Uiso 0.50 1 calc PR . .
H3B H 0.3406 0.1734 0.5987 0.055 Uiso 0.50 1 calc PR . .
C4 C 0.2112(4) 0.2500 0.6459(4) 0.0486(13) Uani 1 2 d S . .
H4A H 0.2105 0.1733 0.6890 0.058 Uiso 0.50 1 calc PR . .
H4B H 0.2105 0.3267 0.6890 0.058 Uiso 0.50 1 calc PR . .
C5 C 0.2192(4) 0.1332(7) 0.4540(5) 0.096(2) Uani 1 1 d U . .
H5A H 0.2029 0.1296 0.3827 0.115 Uiso 1 1 calc R . .
H5B H 0.2566 0.0556 0.4701 0.115 Uiso 1 1 calc R . .
C6 C 0.1285(3) 0.1320(3) 0.5137(3) 0.0512(9) Uani 1 1 d . . .
H6A H 0.1262 0.0536 0.5549 0.061 Uiso 1 1 calc R . .
H6B H 0.0731 0.1310 0.4685 0.061 Uiso 1 1 calc R . .
C7 C 0.0256(4) 0.2500 0.6414(5) 0.0607(16) Uani 1 2 d S . .
H7 H -0.0278 0.2500 0.5925 0.073 Uiso 1 2 calc SR . .
C8 C 0.0161(4) 0.3697(5) 0.7043(5) 0.097(2) Uani 1 1 d . . .
H8A H -0.0478 0.3732 0.7331 0.146 Uiso 1 1 calc R . .
H8B H 0.0265 0.4455 0.6630 0.146 Uiso 1 1 calc R . .
H8C H 0.0635 0.3678 0.7574 0.146 Uiso 1 1 calc R . .
N1 N 0.2796(3) 0.2500 0.4729(3) 0.0492(11) Uani 1 2 d S . .
N2 N 0.1235(3) 0.2500 0.5803(3) 0.0437(10) Uani 1 2 d S . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 Cl3 2.332(12) . ?
Mn1 Cl2 2.3706(10) 8_575 ?
Mn1 Cl2 2.3706(10) . ?
Mn1 Br1 2.452(3) . ?
Mn1 Cl1 2.459(18) . ?
Mn1 Br3 2.462(12) . ?
C1 C2 1.494(8) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C1 1.494(8) 8_565 ?
C2 N1 1.539(8) . ?
C2 H2 0.9800 . ?
C3 N1 1.485(6) . ?
C3 C4 1.509(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N2 1.488(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.478(6) . ?
C5 N1 1.479(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 N2 1.497(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.487(6) 8_565 ?
C7 C8 1.487(6) . ?
C7 N2 1.573(7) . ?
C7 H7 0.9800 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
N1 C5 1.479(6) 8_565 ?
N2 C6 1.497(4) 8_565 ?

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
Cl3 Mn1 Cl2 108.37(11) . 8_575 ?
Cl3 Mn1 Cl2 108.37(11) . . ?
Cl2 Mn1 Cl2 105.05(6) 8_575 . ?
Cl3 Mn1 Br1 107.1(2) . . ?
Cl2 Mn1 Br1 113.87(5) 8_575 . ?
Cl2 Mn1 Br1 113.87(5) . . ?
Cl3 Mn1 Cl1 101.3(3) . . ?
Cl2 Mn1 Cl1 116.67(12) 8_575 . ?
Cl2 Mn1 Cl1 116.67(12) . . ?
Br1 Mn1 Cl1 5.8(3) . . ?
Cl3 Mn1 Br3 2.5(3) . . ?
Cl2 Mn1 Br3 106.99(10) 8_575 . ?
Cl2 Mn1 Br3 106.99(10) . . ?
Br1 Mn1 Br3 109.60(18) . . ?
Cl1 Mn1 Br3 103.8(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 C1 111.4(7) 8_565 . ?
C1 C2 N1 111.5(4) 8_565 . ?
C1 C2 N1 111.5(4) . . ?
C1 C2 H2 107.4 8_565 . ?
C1 C2 H2 107.4 . . ?
N1 C2 H2 107.4 . . ?
N1 C3 C4 111.7(4) . . ?
N1 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
N1 C3 H3B 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
N2 C4 C3 110.5(4) . . ?
N2 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
N2 C4 H4B 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C6 C5 N1 113.1(4) . . ?
C6 C5 H5A 109.0 . . ?
N1 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
N1 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C5 C6 N2 110.4(4) . . ?
C5 C6 H6A 109.6 . . ?
N2 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
N2 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 C8 111.0(6) 8_565 . ?
C8 C7 N2 111.3(3) 8_565 . ?
C8 C7 N2 111.3(3) . . ?
C8 C7 H7 107.7 8_565 . ?
C8 C7 H7 107.7 . . ?
N2 C7 H7 107.7 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 N1 C5 107.9(6) . 8_565 ?
C5 N1 C3 106.5(4) . . ?
C5 N1 C3 106.5(4) 8_565 . ?
C5 N1 C2 111.5(3) . . ?
C5 N1 C2 111.5(3) 8_565 . ?
C3 N1 C2 112.6(5) . . ?
C4 N2 C6 107.8(3) . . ?
C4 N2 C6 107.8(3) . 8_565 ?
C6 N2 C6 107.6(4) . 8_565 ?
C4 N2 C7 113.3(4) . . ?
C6 N2 C7 110.1(3) . . ?
C6 N2 C7 110.1(3) 8_565 . ?

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 C3 C4 N2 0.0 . . . . ?
N1 C5 C6 N2 -1.4(7) . . . . ?
C6 C5 N1 C5 -55.2(8) . . . 8_565 ?
C6 C5 N1 C3 58.8(6) . . . . ?
C6 C5 N1 C2 -178.0(5) . . . . ?
C4 C3 N1 C5 -57.5(3) . . . . ?
C4 C3 N1 C5 57.5(3) . . . 8_565 ?
C4 C3 N1 C2 180.0 . . . . ?
C1 C2 N1 C5 177.8(5) 8_565 . . . ?
C1 C2 N1 C5 -57.1(7) . . . . ?
C1 C2 N1 C5 57.1(7) 8_565 . . 8_565 ?
C1 C2 N1 C5 -177.8(5) . . . 8_565 ?
C1 C2 N1 C3 -62.6(5) 8_565 . . . ?
C1 C2 N1 C3 62.6(5) . . . . ?
C3 C4 N2 C6 58.0(3) . . . . ?
C3 C4 N2 C6 -58.0(3) . . . 8_565 ?
C3 C4 N2 C7 180.0 . . . . ?
C5 C6 N2 C4 -57.5(5) . . . . ?
C5 C6 N2 C6 58.6(6) . . . 8_565 ?
C5 C6 N2 C7 178.5(5) . . . . ?
C8 C7 N2 C4 -62.2(5) 8_565 . . . ?
C8 C7 N2 C4 62.2(5) . . . . ?
C8 C7 N2 C6 58.6(6) 8_565 . . . ?
C8 C7 N2 C6 -177.0(4) . . . . ?
C8 C7 N2 C6 177.0(4) 8_565 . . 8_565 ?
C8 C7 N2 C6 -58.6(6) . . . 8_565 ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.68
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.213
_refine_diff_density_min         -1.073
_refine_diff_density_rms         0.147
####################################################################### 
# 
# 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_w1
_database_code_depnum_ccdc_archive 'CCDC 1026403'
_audit_update_record             
;
2014-09-26 deposited with the CCDC.
2015-01-13 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 H26 Br Cl3 Mn N2'
_chemical_formula_weight         439.55

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'
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           Orthorhombic
_symmetry_space_group_name_H-M   'P2(1)2(1)2(1) '

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

_cell_length_a                   10.1863(8)
_cell_length_b                   13.1566(11)
_cell_length_c                   13.6378(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1827.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    9916
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      27.32
_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             892
_exptl_absorpt_coefficient_mu    3.337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3487
_exptl_absorpt_correction_T_max  0.5550
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      153(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13842
_diffrn_reflns_av_R_equivalents  0.0151
_diffrn_reflns_av_sigmaI/netI    0.0135
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         25.67
_reflns_number_total             3461
_reflns_number_gt                3372
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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+0.6990P] 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   0.487(13)
_refine_ls_number_reflns         3461
_refine_ls_number_parameters     198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.1118
_refine_ls_wR_factor_gt          0.1068
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.24058(5) 0.35866(4) 0.74296(4) 0.02224(16) Uani 1 1 d . . .
Br4 Br 0.2231(2) 0.17384(16) 0.77456(14) 0.0466(5) Uani 0.75 1 d P A 1
Cl4 Cl 0.2287(16) 0.1735(10) 0.7584(7) 0.0207(18) Uani 0.25 1 d P A 2
C1 C 0.6437(4) 0.4664(3) 0.5147(4) 0.0392(10) Uani 1 1 d . . .
H1A H 0.6590 0.5229 0.5601 0.059 Uiso 1 1 calc R . .
H1B H 0.5590 0.4346 0.5295 0.059 Uiso 1 1 calc R . .
H1C H 0.6429 0.4921 0.4472 0.059 Uiso 1 1 calc R . .
C2 C 0.7525(4) 0.3884(3) 0.5258(3) 0.0294(8) Uani 1 1 d . . .
H2 H 0.7441 0.3386 0.4707 0.035 Uiso 1 1 calc R . .
C3 C 0.8860(4) 0.4391(4) 0.5169(4) 0.0438(11) Uani 1 1 d . . .
H3A H 0.8916 0.4750 0.4541 0.066 Uiso 1 1 calc R . .
H3B H 0.9551 0.3874 0.5202 0.066 Uiso 1 1 calc R . .
H3C H 0.8974 0.4877 0.5707 0.066 Uiso 1 1 calc R . .
C4 C 0.6210(4) 0.2598(3) 0.6204(3) 0.0252(8) Uani 1 1 d . . .
H4A H 0.6377 0.2026 0.5749 0.030 Uiso 1 1 calc R . .
H4B H 0.5436 0.2978 0.5962 0.030 Uiso 1 1 calc R . .
C5 C 0.5934(3) 0.2189(3) 0.7228(3) 0.0239(7) Uani 1 1 d . . .
H5A H 0.5242 0.2601 0.7546 0.029 Uiso 1 1 calc R . .
H5B H 0.5622 0.1478 0.7186 0.029 Uiso 1 1 calc R . .
C6 C 0.7250(3) 0.3970(2) 0.7113(3) 0.0206(7) Uani 1 1 d . . .
H6A H 0.6366 0.4284 0.7122 0.025 Uiso 1 1 calc R . .
H6B H 0.7911 0.4521 0.7085 0.025 Uiso 1 1 calc R . .
C7 C 0.7452(4) 0.3335(2) 0.8040(2) 0.0218(7) Uani 1 1 d . . .
H7A H 0.8366 0.3412 0.8274 0.026 Uiso 1 1 calc R . .
H7B H 0.6855 0.3577 0.8563 0.026 Uiso 1 1 calc R . .
C8 C 0.8581(3) 0.2625(3) 0.6395(3) 0.0234(7) Uani 1 1 d . . .
H8A H 0.9330 0.3049 0.6611 0.028 Uiso 1 1 calc R . .
H8B H 0.8828 0.2283 0.5776 0.028 Uiso 1 1 calc R . .
C9 C 0.8265(4) 0.1830(3) 0.7180(3) 0.0257(8) Uani 1 1 d . . .
H9A H 0.7986 0.1187 0.6865 0.031 Uiso 1 1 calc R . .
H9B H 0.9055 0.1690 0.7581 0.031 Uiso 1 1 calc R . .
C10 C 0.7072(4) 0.1577(3) 0.8755(3) 0.0326(9) Uani 1 1 d . . .
H10 H 0.7050 0.0849 0.8546 0.039 Uiso 1 1 calc R . .
C11 C 0.5812(5) 0.1796(4) 0.9308(3) 0.0444(11) Uani 1 1 d . . .
H11A H 0.5767 0.1363 0.9891 0.067 Uiso 1 1 calc R . .
H11B H 0.5058 0.1655 0.8883 0.067 Uiso 1 1 calc R . .
H11C H 0.5797 0.2512 0.9507 0.067 Uiso 1 1 calc R . .
C12 C 0.8268(5) 0.1722(4) 0.9406(4) 0.0497(12) Uani 1 1 d . . .
H12A H 0.8194 0.2369 0.9758 0.075 Uiso 1 1 calc R . .
H12B H 0.9062 0.1729 0.9000 0.075 Uiso 1 1 calc R . .
H12C H 0.8320 0.1163 0.9879 0.075 Uiso 1 1 calc R . .
Cl1 Cl 0.2793(6) 0.3852(4) 0.5720(4) 0.0573(17) Uani 0.75 1 d P A 1
Br1 Br 0.2810(4) 0.3873(2) 0.5691(3) 0.0168(9) Uani 0.25 1 d P A 2
Cl2 Cl 0.41863(7) 0.44481(6) 0.82134(5) 0.01483(18) Uani 1 1 d . A .
Cl3 Cl 0.04788(8) 0.44268(7) 0.79293(7) 0.0282(2) Uani 1 1 d . A .
N1 N 0.7386(3) 0.3288(2) 0.6230(2) 0.0212(6) Uani 1 1 d . . .
N2 N 0.7176(3) 0.2236(2) 0.7822(2) 0.0205(6) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 Cl3 2.3536(10) . ?
Mn1 Cl1 2.390(5) . ?
Mn1 Cl2 2.3909(8) . ?
Mn1 Br1 2.436(4) . ?
Mn1 Cl4 2.448(13) . ?
Mn1 Br4 2.476(2) . ?
C1 C2 1.519(6) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.519(6) . ?
C2 N1 1.546(4) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 N1 1.504(4) . ?
C4 C5 1.522(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N2 1.504(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N1 1.508(4) . ?
C6 C7 1.529(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.503(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N1 1.514(4) . ?
C8 C9 1.530(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N2 1.511(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.516(6) . ?
C10 C12 1.519(6) . ?
C10 N2 1.544(4) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl3 Mn1 Cl1 110.57(15) . . ?
Cl3 Mn1 Cl2 106.29(3) . . ?
Cl1 Mn1 Cl2 103.99(14) . . ?
Cl3 Mn1 Br1 110.49(9) . . ?
Cl1 Mn1 Br1 0.57(18) . . ?
Cl2 Mn1 Br1 103.51(9) . . ?
Cl3 Mn1 Cl4 113.7(4) . . ?
Cl1 Mn1 Cl4 103.7(2) . . ?
Cl2 Mn1 Cl4 118.1(4) . . ?
Br1 Mn1 Cl4 104.2(2) . . ?
Cl3 Mn1 Br4 110.53(6) . . ?
Cl1 Mn1 Br4 108.98(12) . . ?
Cl2 Mn1 Br4 116.26(6) . . ?
Br1 Mn1 Br4 109.50(8) . . ?
Cl4 Mn1 Br4 5.3(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 C3 110.4(4) . . ?
C1 C2 N1 111.2(3) . . ?
C3 C2 N1 111.9(3) . . ?
C1 C2 H2 107.7 . . ?
C3 C2 H2 107.7 . . ?
N1 C2 H2 107.7 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 C5 109.8(3) . . ?
N1 C4 H4A 109.7 . . ?
C5 C4 H4A 109.7 . . ?
N1 C4 H4B 109.7 . . ?
C5 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
N2 C5 C4 109.0(3) . . ?
N2 C5 H5A 109.9 . . ?
C4 C5 H5A 109.9 . . ?
N2 C5 H5B 109.9 . . ?
C4 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
N1 C6 C7 108.8(3) . . ?
N1 C6 H6A 109.9 . . ?
C7 C6 H6A 109.9 . . ?
N1 C6 H6B 109.9 . . ?
C7 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
N2 C7 C6 109.7(3) . . ?
N2 C7 H7A 109.7 . . ?
C6 C7 H7A 109.7 . . ?
N2 C7 H7B 109.7 . . ?
C6 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
N1 C8 C9 109.2(3) . . ?
N1 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
N1 C8 H8B 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
N2 C9 C8 108.5(3) . . ?
N2 C9 H9A 110.0 . . ?
C8 C9 H9A 110.0 . . ?
N2 C9 H9B 110.0 . . ?
C8 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
C11 C10 C12 111.4(4) . . ?
C11 C10 N2 111.2(3) . . ?
C12 C10 N2 110.8(3) . . ?
C11 C10 H10 107.7 . . ?
C12 C10 H10 107.7 . . ?
N2 C10 H10 107.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C4 N1 C6 107.8(3) . . ?
C4 N1 C8 107.2(2) . . ?
C6 N1 C8 107.4(3) . . ?
C4 N1 C2 111.0(3) . . ?
C6 N1 C2 113.1(3) . . ?
C8 N1 C2 110.2(3) . . ?
C7 N2 C5 107.6(3) . . ?
C7 N2 C9 108.6(3) . . ?
C5 N2 C9 106.9(3) . . ?
C7 N2 C10 112.9(3) . . ?
C5 N2 C10 111.3(3) . . ?
C9 N2 C10 109.3(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C4 C5 N2 -23.3(4) . . . . ?
N1 C6 C7 N2 -22.7(4) . . . . ?
N1 C8 C9 N2 -24.9(4) . . . . ?
C5 C4 N1 C6 -44.2(4) . . . . ?
C5 C4 N1 C8 71.1(3) . . . . ?
C5 C4 N1 C2 -168.5(3) . . . . ?
C7 C6 N1 C4 70.5(3) . . . . ?
C7 C6 N1 C8 -44.7(3) . . . . ?
C7 C6 N1 C2 -166.5(3) . . . . ?
C9 C8 N1 C4 -42.9(4) . . . . ?
C9 C8 N1 C6 72.6(3) . . . . ?
C9 C8 N1 C2 -163.8(3) . . . . ?
C1 C2 N1 C4 69.5(4) . . . . ?
C3 C2 N1 C4 -166.6(3) . . . . ?
C1 C2 N1 C6 -51.8(4) . . . . ?
C3 C2 N1 C6 72.2(4) . . . . ?
C1 C2 N1 C8 -171.9(3) . . . . ?
C3 C2 N1 C8 -48.0(4) . . . . ?
C6 C7 N2 C5 -44.6(4) . . . . ?
C6 C7 N2 C9 70.7(3) . . . . ?
C6 C7 N2 C10 -167.9(3) . . . . ?
C4 C5 N2 C7 71.2(3) . . . . ?
C4 C5 N2 C9 -45.3(4) . . . . ?
C4 C5 N2 C10 -164.6(3) . . . . ?
C8 C9 N2 C7 -42.8(4) . . . . ?
C8 C9 N2 C5 73.1(3) . . . . ?
C8 C9 N2 C10 -166.4(3) . . . . ?
C11 C10 N2 C7 72.1(4) . . . . ?
C12 C10 N2 C7 -52.4(5) . . . . ?
C11 C10 N2 C5 -49.2(4) . . . . ?
C12 C10 N2 C5 -173.7(4) . . . . ?
C11 C10 N2 C9 -167.0(3) . . . . ?
C12 C10 N2 C9 68.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.67
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.649
_refine_diff_density_min         -0.786
_refine_diff_density_rms         0.106
