# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_mait15
_database_code_depnum_ccdc_archive 'CCDC 1039217'
_audit_update_record             
;
2014-12-15 deposited with the CCDC.
2015-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H32 Cl2 Co N7 O3'
_chemical_formula_weight         596.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8871(11)
_cell_length_b                   11.2870(16)
_cell_length_c                   15.565(2)
_cell_angle_alpha                72.418(2)
_cell_angle_beta                 88.268(2)
_cell_angle_gamma                80.936(2)
_cell_volume                     1304.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9910
_cell_measurement_theta_min      2.672
_cell_measurement_theta_max      28.135

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_F_000             620
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.137
_exptl_crystal_size_mid          0.044
_exptl_crystal_size_min          0.028
_exptl_absorpt_coefficient_mu    0.904
_shelx_estimated_absorpt_T_min   0.886
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9749
_exptl_absorpt_correction_T_max  0.8853
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Apex II Quazar'
_diffrn_measurement_method       'combined omega- and phi-scan'
_diffrn_detector_area_resol_mean 66
_diffrn_reflns_number            22796
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.373
_diffrn_reflns_theta_max         28.445
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6070
_reflns_number_gt                5036
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX II (Bruker, 2007)'
_computing_cell_refinement       'APEX II (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XPMA (Zsolnai, 1996), ORTEP (Farrugia, 1997)'
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0276P)²+0.9233P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6070
_refine_ls_number_parameters     351
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0692
_refine_ls_wR_factor_gt          0.0645
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.30375(3) 0.37560(2) 0.18754(2) 0.01053(6) Uani 1 1 d . . . . .
Cl1 Cl 0.43157(5) 0.20182(4) 0.29251(3) 0.01559(9) Uani 1 1 d . . . . .
Cl2 Cl 0.19016(5) 0.54969(4) 0.07717(3) 0.01375(9) Uani 1 1 d . . . . .
O1 O -0.09432(15) 0.22612(11) 0.13837(8) 0.0172(3) Uani 1 1 d . . . . .
O2 O 0.32724(15) 0.54766(11) 0.37502(8) 0.0165(2) Uani 1 1 d . . . . .
N1 N 0.33939(18) 0.27954(13) 0.10045(9) 0.0142(3) Uani 1 1 d . . . . .
N3 N 0.09274(17) 0.31611(13) 0.20407(9) 0.0126(3) Uani 1 1 d . . . . .
N4 N 0.23206(17) 0.44665(13) 0.27994(9) 0.0119(3) Uani 1 1 d . . . . .
N5 N 0.50117(17) 0.46167(12) 0.18413(9) 0.0116(3) Uani 1 1 d . . . . .
N7 N 1.07739(18) 1.11118(13) -0.31240(10) 0.0161(3) Uani 1 1 d . . . . .
C1 C 0.4805(2) 0.24373(16) 0.05854(12) 0.0182(4) Uani 1 1 d . . . . .
H1 H 0.5860 0.2698 0.0670 0.020(3) Uiso 1 1 calc R U . . .
C2 C 0.4730(2) 0.16871(17) 0.00286(12) 0.0226(4) Uani 1 1 d . . . . .
H2 H 0.5754 0.1440 -0.0253 0.020(3) Uiso 1 1 calc R U . . .
N2 N 0.3294(2) 0.12963(15) -0.01302(11) 0.0237(3) Uani 1 1 d . . . . .
C3 C 0.1901(2) 0.16554(16) 0.02974(12) 0.0195(4) Uani 1 1 d . . . . .
H3 H 0.0845 0.1404 0.0202 0.020(3) Uiso 1 1 calc R U . . .
C4 C 0.1937(2) 0.23799(15) 0.08741(11) 0.0149(3) Uani 1 1 d . . . . .
C5 C 0.0439(2) 0.26208(15) 0.14545(11) 0.0138(3) Uani 1 1 d . . . . .
C6 C 0.0005(2) 0.33829(15) 0.27789(11) 0.0117(3) Uani 1 1 d . . . . .
C7 C -0.1518(2) 0.29455(15) 0.31113(11) 0.0136(3) Uani 1 1 d . . . . .
H7 H -0.2048 0.2460 0.2826 0.018(2) Uiso 1 1 calc R U . . .
C8 C -0.2251(2) 0.32281(16) 0.38641(11) 0.0149(3) Uani 1 1 d . . . . .
H8 H -0.3280 0.2924 0.4097 0.018(2) Uiso 1 1 calc R U . . .
C9 C -0.1493(2) 0.39515(16) 0.42792(11) 0.0164(3) Uani 1 1 d . . . . .
H9 H -0.2014 0.4142 0.4790 0.018(2) Uiso 1 1 calc R U . . .
C10 C 0.0020(2) 0.43971(16) 0.39532(11) 0.0144(3) Uani 1 1 d . . . . .
H10 H 0.0527 0.4896 0.4236 0.018(2) Uiso 1 1 calc R U . . .
C11 C 0.0787(2) 0.41067(15) 0.32087(11) 0.0120(3) Uani 1 1 d . . . . .
C12 C 0.3407(2) 0.50586(15) 0.30846(11) 0.0123(3) Uani 1 1 d . . . . .
C13 C 0.4917(2) 0.52130(15) 0.24777(11) 0.0124(3) Uani 1 1 d . . . . .
C14 C 0.6130(2) 0.59512(15) 0.25321(11) 0.0146(3) Uani 1 1 d . . . . .
H14 H 0.6032 0.6350 0.2992 0.016(3) Uiso 1 1 calc R U . . .
N6 N 0.74394(18) 0.61245(13) 0.19595(10) 0.0167(3) Uani 1 1 d . . . . .
C15 C 0.7519(2) 0.55271(16) 0.13359(11) 0.0155(3) Uani 1 1 d . . . . .
H15 H 0.8436 0.5614 0.0923 0.016(3) Uiso 1 1 calc R U . . .
C16 C 0.6315(2) 0.47824(15) 0.12650(11) 0.0140(3) Uani 1 1 d . . . . .
H16 H 0.6417 0.4386 0.0803 0.016(3) Uiso 1 1 calc R U . . .
C17 C 1.2252(2) 1.02320(16) -0.25475(13) 0.0189(4) Uani 1 1 d . . . . .
H17A H 1.1794 0.9784 -0.1960 0.027(2) Uiso 1 1 calc R U . . .
H17B H 1.2720 0.9594 -0.2846 0.027(2) Uiso 1 1 calc R U . . .
C18 C 1.3707(2) 1.08632(17) -0.23738(13) 0.0216(4) Uani 1 1 d . . . . .
H18A H 1.4107 1.1373 -0.2949 0.044(2) Uiso 1 1 calc R U . . .
H18B H 1.4656 1.0220 -0.2061 0.044(2) Uiso 1 1 calc R U . . .
H18C H 1.3302 1.1405 -0.1999 0.044(2) Uiso 1 1 calc R U . . .
C19 C 0.9434(2) 1.03037(16) -0.31754(12) 0.0190(4) Uani 1 1 d . . . . .
H19A H 0.9978 0.9626 -0.3422 0.027(2) Uiso 1 1 calc R U . . .
H19B H 0.9069 0.9899 -0.2556 0.027(2) Uiso 1 1 calc R U . . .
C20 C 0.7851(2) 1.09949(18) -0.37429(14) 0.0257(4) Uani 1 1 d . . . . .
H20A H 0.7290 1.1665 -0.3504 0.044(2) Uiso 1 1 calc R U . . .
H20B H 0.7054 1.0404 -0.3725 0.044(2) Uiso 1 1 calc R U . . .
H20C H 0.8184 1.1363 -0.4367 0.044(2) Uiso 1 1 calc R U . . .
C21 C 1.1380(3) 1.17666(19) -0.40577(13) 0.0276(4) Uani 1 1 d . . . . .
H21A H 1.0386 1.2333 -0.4410 0.027(2) Uiso 1 1 calc R U . . .
H21B H 1.2226 1.2298 -0.3995 0.027(2) Uiso 1 1 calc R U . . .
C22 C 1.2186(3) 1.0912(3) -0.45891(16) 0.0460(6) Uani 1 1 d . . . . .
H22A H 1.3208 1.0371 -0.4264 0.044(2) Uiso 1 1 calc R U . . .
H22B H 1.2516 1.1420 -0.5181 0.044(2) Uiso 1 1 calc R U . . .
H22C H 1.1358 1.0388 -0.4667 0.044(2) Uiso 1 1 calc R U . . .
C23 C 1.0026(2) 1.21461(17) -0.27196(14) 0.0254(4) Uani 1 1 d . . . . .
H23A H 1.0938 1.2643 -0.2690 0.027(2) Uiso 1 1 calc R U . . .
H23B H 0.9109 1.2716 -0.3131 0.027(2) Uiso 1 1 calc R U . . .
C24 C 0.9288(3) 1.1702(2) -0.17899(16) 0.0408(6) Uani 1 1 d . . . . .
H24A H 0.8308 1.1278 -0.1819 0.044(2) Uiso 1 1 calc R U . . .
H24B H 0.8908 1.2427 -0.1571 0.044(2) Uiso 1 1 calc R U . . .
H24C H 1.0169 1.1114 -0.1378 0.044(2) Uiso 1 1 calc R U . . .
O10 O 0.54956(18) 0.65956(13) 0.45683(10) 0.0255(3) Uani 1 1 d . . . . .
H101 H 0.475(5) 0.608(3) 0.433(3) 0.104(13) Uiso 1 1 d . . . . .
H102 H 0.600(4) 0.596(3) 0.513(2) 0.079(10) Uiso 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
Co1 N3 1.8731(14) . ?
Co1 N4 1.8804(14) . ?
Co1 N5 1.9523(14) . ?
Co1 N1 1.9649(14) . ?
Co1 Cl1 2.2525(5) . ?
Co1 Cl2 2.2614(5) . ?
O1 C5 1.241(2) . ?
O2 C12 1.257(2) . ?
N1 C1 1.342(2) . ?
N1 C4 1.350(2) . ?
N3 C5 1.336(2) . ?
N3 C6 1.406(2) . ?
N4 C12 1.327(2) . ?
N4 C11 1.409(2) . ?
N5 C16 1.341(2) . ?
N5 C13 1.350(2) . ?
N7 C21 1.519(2) . ?
N7 C17 1.520(2) . ?
N7 C19 1.519(2) . ?
N7 C23 1.520(2) . ?
C1 C2 1.391(2) . ?
C2 N2 1.334(3) . ?
N2 C3 1.339(2) . ?
C3 C4 1.388(2) . ?
C4 C5 1.506(2) . ?
C6 C7 1.396(2) . ?
C6 C11 1.417(2) . ?
C7 C8 1.391(2) . ?
C8 C9 1.392(2) . ?
C9 C10 1.390(2) . ?
C10 C11 1.393(2) . ?
C12 C13 1.497(2) . ?
C13 C14 1.384(2) . ?
C14 N6 1.342(2) . ?
N6 C15 1.334(2) . ?
C15 C16 1.391(2) . ?
C17 C18 1.514(2) . ?
C19 C20 1.514(2) . ?
C21 C22 1.509(3) . ?
C23 C24 1.512(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Co1 N4 84.85(6) . . ?
N3 Co1 N5 167.90(6) . . ?
N4 Co1 N5 83.58(6) . . ?
N3 Co1 N1 83.34(6) . . ?
N4 Co1 N1 167.69(6) . . ?
N5 Co1 N1 108.41(6) . . ?
N3 Co1 Cl1 91.23(4) . . ?
N4 Co1 Cl1 89.07(4) . . ?
N5 Co1 Cl1 92.12(4) . . ?
N1 Co1 Cl1 87.71(4) . . ?
N3 Co1 Cl2 91.49(4) . . ?
N4 Co1 Cl2 93.35(4) . . ?
N5 Co1 Cl2 85.65(4) . . ?
N1 Co1 Cl2 90.43(4) . . ?
Cl1 Co1 Cl2 176.504(18) . . ?
C1 N1 C4 117.36(15) . . ?
C1 N1 Co1 131.74(12) . . ?
C4 N1 Co1 110.75(11) . . ?
C5 N3 C6 127.37(14) . . ?
C5 N3 Co1 118.58(11) . . ?
C6 N3 Co1 114.02(11) . . ?
C12 N4 C11 127.29(14) . . ?
C12 N4 Co1 117.87(11) . . ?
C11 N4 Co1 113.87(11) . . ?
C16 N5 C13 117.14(14) . . ?
C16 N5 Co1 131.13(12) . . ?
C13 N5 Co1 111.49(10) . . ?
C21 N7 C17 110.85(14) . . ?
C21 N7 C19 111.00(14) . . ?
C17 N7 C19 106.47(13) . . ?
C21 N7 C23 106.40(14) . . ?
C17 N7 C23 111.36(14) . . ?
C19 N7 C23 110.83(13) . . ?
N1 C1 C2 120.32(17) . . ?
N2 C2 C1 123.29(17) . . ?
C2 N2 C3 115.60(16) . . ?
N2 C3 C4 122.66(17) . . ?
N1 C4 C3 120.71(16) . . ?
N1 C4 C5 116.76(15) . . ?
C3 C4 C5 122.20(16) . . ?
O1 C5 N3 129.80(16) . . ?
O1 C5 C4 120.96(15) . . ?
N3 C5 C4 109.08(14) . . ?
C7 C6 N3 126.52(15) . . ?
C7 C6 C11 119.93(15) . . ?
N3 C6 C11 113.54(14) . . ?
C8 C7 C6 119.32(15) . . ?
C7 C8 C9 120.70(15) . . ?
C10 C9 C8 120.57(16) . . ?
C9 C10 C11 119.52(16) . . ?
C10 C11 N4 126.94(15) . . ?
C10 C11 C6 119.94(15) . . ?
N4 C11 C6 113.11(14) . . ?
O2 C12 N4 128.35(15) . . ?
O2 C12 C13 121.28(15) . . ?
N4 C12 C13 110.36(14) . . ?
N5 C13 C14 120.92(15) . . ?
N5 C13 C12 115.98(14) . . ?
C14 C13 C12 123.07(15) . . ?
N6 C14 C13 122.50(16) . . ?
C15 N6 C14 115.92(15) . . ?
N6 C15 C16 122.74(15) . . ?
N5 C16 C15 120.77(16) . . ?
C18 C17 N7 115.13(14) . . ?
C20 C19 N7 115.33(14) . . ?
C22 C21 N7 115.68(17) . . ?
C24 C23 N7 115.44(16) . . ?

_refine_diff_density_max         0.361
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.060

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_mait16
_database_code_depnum_ccdc_archive 'CCDC 1039218'
_audit_update_record             
;
2014-12-15 deposited with the CCDC.
2015-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H32 Br2 Co N7 O3'
_chemical_formula_weight         685.31

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'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0125(4)
_cell_length_b                   11.3000(6)
_cell_length_c                   15.6292(8)
_cell_angle_alpha                73.0570(10)
_cell_angle_beta                 88.9330(10)
_cell_angle_gamma                81.3510(10)
_cell_volume                     1337.80(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8854
_cell_measurement_theta_min      2.647
_cell_measurement_theta_max      28.22

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_F_000             692
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.044
_exptl_absorpt_coefficient_mu    3.669
_shelx_estimated_absorpt_T_min   0.468
_shelx_estimated_absorpt_T_max   0.855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Apex II Quazar'
_diffrn_measurement_method       'combined omega- and phi-scan'
_diffrn_detector_area_resol_mean 66
_diffrn_reflns_number            24585
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.362
_diffrn_reflns_theta_max         28.529
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.925
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6296
_reflns_number_gt                5341
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX II (Bruker, 2007)'
_computing_cell_refinement       'APEX II (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XPMA (Zsolnai, 1996), ORTEP (Farrugia, 1997)'
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0259P)²+0.8661P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6296
_refine_ls_number_parameters     351
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_ref         0.0611
_refine_ls_wR_factor_gt          0.0579
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.29880(3) 0.37759(2) 0.18926(2) 0.00903(6) Uani 1 1 d . . . . .
Br1 Br 0.42950(2) 0.19435(2) 0.30109(2) 0.01400(6) Uani 1 1 d . . . . .
Br2 Br 0.18295(2) 0.56110(2) 0.07191(2) 0.01200(6) Uani 1 1 d . . . . .
O1 O -0.09235(19) 0.22385(14) 0.14038(10) 0.0162(3) Uani 1 1 d . . . . .
O2 O 0.32292(18) 0.55130(14) 0.37601(10) 0.0154(3) Uani 1 1 d . . . . .
N1 N 0.3331(2) 0.28050(16) 0.10295(11) 0.0123(3) Uani 1 1 d . . . . .
N3 N 0.0902(2) 0.31866(16) 0.20438(11) 0.0114(3) Uani 1 1 d . . . . .
N4 N 0.2286(2) 0.45014(15) 0.28065(11) 0.0101(3) Uani 1 1 d . . . . .
N5 N 0.4942(2) 0.46269(15) 0.18757(11) 0.0097(3) Uani 1 1 d . . . . .
N7 N 1.0706(2) 1.11464(16) -0.31324(12) 0.0155(4) Uani 1 1 d . . . . .
C1 C 0.4714(3) 0.2445(2) 0.06133(14) 0.0173(4) Uani 1 1 d . . . . .
H1 H 0.5754 0.2707 0.0700 0.021(4) Uiso 1 1 calc R U . . .
C2 C 0.4632(3) 0.1695(2) 0.00589(15) 0.0213(5) Uani 1 1 d . . . . .
H2 H 0.5636 0.1449 -0.0219 0.021(4) Uiso 1 1 calc R U . . .
N2 N 0.3215(3) 0.13014(18) -0.01049(13) 0.0235(4) Uani 1 1 d . . . . .
C3 C 0.1850(3) 0.1655(2) 0.03190(14) 0.0186(5) Uani 1 1 d . . . . .
H3 H 0.0811 0.1399 0.0222 0.021(4) Uiso 1 1 calc R U . . .
C4 C 0.1892(3) 0.23824(19) 0.08954(13) 0.0138(4) Uani 1 1 d . . . . .
C5 C 0.0430(3) 0.26194(18) 0.14693(13) 0.0120(4) Uani 1 1 d . . . . .
C6 C 0.0001(2) 0.34247(18) 0.27696(13) 0.0109(4) Uani 1 1 d . . . . .
C7 C -0.1495(2) 0.29805(19) 0.30964(13) 0.0116(4) Uani 1 1 d . . . . .
H7 H -0.2011 0.2482 0.2815 0.015(3) Uiso 1 1 calc R U . . .
C8 C -0.2218(2) 0.32789(19) 0.38391(13) 0.0135(4) Uani 1 1 d . . . . .
H8 H -0.3230 0.2977 0.4068 0.015(3) Uiso 1 1 calc R U . . .
C9 C -0.1472(3) 0.4013(2) 0.42481(14) 0.0142(4) Uani 1 1 d . . . . .
H9 H -0.1985 0.4214 0.4751 0.015(3) Uiso 1 1 calc R U . . .
C10 C 0.0015(2) 0.44567(19) 0.39320(13) 0.0119(4) Uani 1 1 d . . . . .
H10 H 0.0513 0.4964 0.4213 0.015(3) Uiso 1 1 calc R U . . .
C11 C 0.0771(2) 0.41498(18) 0.31976(13) 0.0106(4) Uani 1 1 d . . . . .
C12 C 0.3359(2) 0.50901(18) 0.31004(13) 0.0108(4) Uani 1 1 d . . . . .
C13 C 0.4848(2) 0.52304(18) 0.25084(13) 0.0108(4) Uani 1 1 d . . . . .
C14 C 0.6046(3) 0.59720(19) 0.25681(14) 0.0136(4) Uani 1 1 d . . . . .
H14 H 0.5954 0.6373 0.3027 0.014(3) Uiso 1 1 calc R U . . .
N6 N 0.7330(2) 0.61464(17) 0.20036(12) 0.0156(4) Uani 1 1 d . . . . .
C15 C 0.7404(3) 0.55359(19) 0.13848(14) 0.0141(4) Uani 1 1 d . . . . .
H15 H 0.8302 0.5621 0.0976 0.014(3) Uiso 1 1 calc R U . . .
C16 C 0.6227(2) 0.47843(19) 0.13144(13) 0.0122(4) Uani 1 1 d . . . . .
H16 H 0.6333 0.4375 0.0860 0.014(3) Uiso 1 1 calc R U . . .
C17 C 1.2174(3) 1.0251(2) -0.25839(15) 0.0182(5) Uani 1 1 d . . . . .
H17A H 1.1738 0.9767 -0.2012 0.024(2) Uiso 1 1 calc R U . . .
H17B H 1.2630 0.9649 -0.2912 0.024(2) Uiso 1 1 calc R U . . .
C18 C 1.3607(3) 1.0864(2) -0.23755(16) 0.0221(5) Uani 1 1 d . . . . .
H18A H 1.4017 1.1381 -0.2934 0.041(2) Uiso 1 1 calc R U . . .
H18B H 1.4530 1.0217 -0.2065 0.041(2) Uiso 1 1 calc R U . . .
H18C H 1.3204 1.1392 -0.1993 0.041(2) Uiso 1 1 calc R U . . .
C19 C 0.9406(3) 1.0349(2) -0.32402(15) 0.0180(5) Uani 1 1 d . . . . .
H19A H 0.9050 0.9897 -0.2639 0.024(2) Uiso 1 1 calc R U . . .
H19B H 0.9950 0.9714 -0.3521 0.024(2) Uiso 1 1 calc R U . . .
C20 C 0.7842(3) 1.1068(2) -0.37958(17) 0.0263(5) Uani 1 1 d . . . . .
H20A H 0.7288 1.1699 -0.3524 0.041(2) Uiso 1 1 calc R U . . .
H20B H 0.7060 1.0487 -0.3817 0.041(2) Uiso 1 1 calc R U . . .
H20C H 0.8168 1.1481 -0.4405 0.041(2) Uiso 1 1 calc R U . . .
C21 C 1.1296(3) 1.1865(2) -0.40357(16) 0.0263(6) Uani 1 1 d . . . . .
H21A H 1.0318 1.2453 -0.4366 0.024(2) Uiso 1 1 calc R U . . .
H21B H 1.2137 1.2373 -0.3935 0.024(2) Uiso 1 1 calc R U . . .
C22 C 1.2068(4) 1.1087(3) -0.46193(19) 0.0453(8) Uani 1 1 d . . . . .
H22A H 1.3073 1.0528 -0.4315 0.041(2) Uiso 1 1 calc R U . . .
H22B H 1.2388 1.1639 -0.5188 0.041(2) Uiso 1 1 calc R U . . .
H22C H 1.1245 1.0589 -0.4735 0.041(2) Uiso 1 1 calc R U . . .
C23 C 0.9966(3) 1.2108(2) -0.26738(17) 0.0247(5) Uani 1 1 d . . . . .
H23A H 0.9053 1.2692 -0.3065 0.024(2) Uiso 1 1 calc R U . . .
H23B H 1.0855 1.2600 -0.2610 0.024(2) Uiso 1 1 calc R U . . .
C24 C 0.9258(4) 1.1577(3) -0.1760(2) 0.0415(7) Uani 1 1 d . . . . .
H24A H 0.8313 1.1145 -0.1819 0.041(2) Uiso 1 1 calc R U . . .
H24B H 0.8860 1.2259 -0.1502 0.041(2) Uiso 1 1 calc R U . . .
H24C H 1.0142 1.0984 -0.1368 0.041(2) Uiso 1 1 calc R U . . .
O10 O 0.5487(2) 0.65946(17) 0.45948(12) 0.0278(4) Uani 1 1 d . . . . .
H101 H 0.467(6) 0.609(4) 0.432(3) 0.119(17) Uiso 1 1 d . . . . .
H102 H 0.605(7) 0.587(6) 0.518(4) 0.16(2) Uiso 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
Co1 N3 1.8764(16) . ?
Co1 N4 1.8822(17) . ?
Co1 N5 1.9527(17) . ?
Co1 N1 1.9640(17) . ?
Co1 Br1 2.3970(3) . ?
Co1 Br2 2.4070(3) . ?
O1 C5 1.242(2) . ?
O2 C12 1.253(2) . ?
N1 C1 1.345(3) . ?
N1 C4 1.354(3) . ?
N3 C5 1.335(3) . ?
N3 C6 1.404(3) . ?
N4 C12 1.326(3) . ?
N4 C11 1.407(2) . ?
N5 C16 1.338(2) . ?
N5 C13 1.350(3) . ?
N7 C23 1.514(3) . ?
N7 C21 1.516(3) . ?
N7 C19 1.518(3) . ?
N7 C17 1.522(3) . ?
C1 C2 1.386(3) . ?
C2 N2 1.335(3) . ?
N2 C3 1.339(3) . ?
C3 C4 1.389(3) . ?
C4 C5 1.501(3) . ?
C6 C7 1.399(3) . ?
C6 C11 1.410(3) . ?
C7 C8 1.393(3) . ?
C8 C9 1.388(3) . ?
C9 C10 1.389(3) . ?
C10 C11 1.396(3) . ?
C12 C13 1.495(3) . ?
C13 C14 1.387(3) . ?
C14 N6 1.342(3) . ?
N6 C15 1.338(3) . ?
C15 C16 1.387(3) . ?
C17 C18 1.514(3) . ?
C19 C20 1.519(3) . ?
C21 C22 1.507(4) . ?
C23 C24 1.514(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
N3 Co1 N4 84.88(7) . . ?
N3 Co1 N5 167.90(7) . . ?
N4 Co1 N5 83.49(7) . . ?
N3 Co1 N1 83.29(7) . . ?
N4 Co1 N1 167.69(7) . . ?
N5 Co1 N1 108.50(7) . . ?
N3 Co1 Br1 90.95(5) . . ?
N4 Co1 Br1 89.00(5) . . ?
N5 Co1 Br1 92.18(5) . . ?
N1 Co1 Br1 87.80(5) . . ?
N3 Co1 Br2 91.77(5) . . ?
N4 Co1 Br2 93.39(5) . . ?
N5 Co1 Br2 85.60(5) . . ?
N1 Co1 Br2 90.38(5) . . ?
Br1 Co1 Br2 176.534(14) . . ?
C1 N1 C4 117.15(18) . . ?
C1 N1 Co1 131.95(15) . . ?
C4 N1 Co1 110.77(14) . . ?
C5 N3 C6 127.56(17) . . ?
C5 N3 Co1 118.69(14) . . ?
C6 N3 Co1 113.75(13) . . ?
C12 N4 C11 127.48(17) . . ?
C12 N4 Co1 118.00(13) . . ?
C11 N4 Co1 113.51(13) . . ?
C16 N5 C13 117.10(17) . . ?
C16 N5 Co1 131.25(15) . . ?
C13 N5 Co1 111.39(13) . . ?
C23 N7 C21 106.71(17) . . ?
C23 N7 C19 111.09(17) . . ?
C21 N7 C19 110.91(17) . . ?
C23 N7 C17 111.23(17) . . ?
C21 N7 C17 110.50(17) . . ?
C19 N7 C17 106.45(16) . . ?
N1 C1 C2 120.5(2) . . ?
N2 C2 C1 123.3(2) . . ?
C2 N2 C3 115.7(2) . . ?
N2 C3 C4 122.6(2) . . ?
N1 C4 C3 120.7(2) . . ?
N1 C4 C5 116.79(18) . . ?
C3 C4 C5 122.20(19) . . ?
O1 C5 N3 129.6(2) . . ?
O1 C5 C4 120.95(18) . . ?
N3 C5 C4 109.25(17) . . ?
C7 C6 N3 126.13(19) . . ?
C7 C6 C11 120.10(18) . . ?
N3 C6 C11 113.73(17) . . ?
C8 C7 C6 119.15(19) . . ?
C9 C8 C7 120.55(19) . . ?
C8 C9 C10 120.87(19) . . ?
C9 C10 C11 119.35(19) . . ?
C10 C11 N4 126.50(19) . . ?
C10 C11 C6 119.96(18) . . ?
N4 C11 C6 113.54(17) . . ?
O2 C12 N4 128.42(18) . . ?
O2 C12 C13 121.40(17) . . ?
N4 C12 C13 110.17(17) . . ?
N5 C13 C14 120.76(18) . . ?
N5 C13 C12 116.21(17) . . ?
C14 C13 C12 122.98(19) . . ?
N6 C14 C13 122.7(2) . . ?
C15 N6 C14 115.60(18) . . ?
N6 C15 C16 122.80(19) . . ?
N5 C16 C15 121.1(2) . . ?
C18 C17 N7 115.14(17) . . ?
N7 C19 C20 114.90(18) . . ?
C22 C21 N7 116.0(2) . . ?
N7 C23 C24 115.1(2) . . ?

_refine_diff_density_max         0.382
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.079

_shelxl_version_number           2013-2

