# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ldf

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H30 Cl Co N4 O7'
_chemical_formula_weight         688.99

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   10.4178(12)
_cell_length_b                   12.0725(14)
_cell_length_c                   13.2955(16)
_cell_angle_alpha                90.683(2)
_cell_angle_beta                 110.550(2)
_cell_angle_gamma                96.916(2)
_cell_volume                     1551.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.11
_cell_measurement_theta_max      27.21

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.784
_exptl_absorpt_correction_T_max  0.870
_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_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8839
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0543
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.11
_diffrn_reflns_theta_max         27.21
_reflns_number_total             6387
_reflns_number_gt                4737
_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)+(0.1000P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6387
_refine_ls_number_parameters     417
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.1700
_refine_ls_wR_factor_gt          0.1486
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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
Co1 Co 0.51018(4) 0.18034(3) 0.58253(3) 0.03322(16) Uani 1 1 d . . .
Cl1 Cl 1.01952(13) -0.34585(10) 0.85206(10) 0.0773(4) Uani 1 1 d . . .
O1 O 0.5681(2) 0.05035(17) 0.66450(16) 0.0368(5) Uani 1 1 d . . .
O2 O 0.6174(2) 0.14443(17) 0.49957(18) 0.0401(5) Uani 1 1 d . . .
O3 O 0.7865(3) 0.0746(2) 0.4172(2) 0.0520(6) Uani 1 1 d . . .
O4 O 0.6103(3) 0.4297(2) 0.7111(2) 0.0577(7) Uani 1 1 d . . .
O5 O 0.6718(2) 0.26234(18) 0.68114(18) 0.0415(5) Uani 1 1 d . . .
O6 O 0.3531(2) 0.08136(18) 0.48015(18) 0.0394(5) Uani 1 1 d . . .
O7 O 0.9114(4) 0.1494(4) 0.6834(4) 0.1188(14) Uani 1 1 d . . .
N1 N 0.6738(3) 0.0087(3) 0.8420(2) 0.0487(7) Uani 1 1 d . . .
N2 N 0.6811(3) 0.0425(3) 0.9469(2) 0.0563(8) Uani 1 1 d . . .
N3 N 0.3976(3) 0.2176(2) 0.6631(2) 0.0343(6) Uani 1 1 d . . .
N4 N 0.4464(3) 0.3027(2) 0.5020(2) 0.0360(6) Uani 1 1 d . . .
C1 C 0.9162(4) -0.2406(3) 0.8391(3) 0.0531(9) Uani 1 1 d . . .
C2 C 0.7738(4) -0.2673(4) 0.8025(3) 0.0588(10) Uani 1 1 d . . .
H2B H 0.7327 -0.3404 0.7801 0.071 Uiso 1 1 calc R . .
C3 C 0.6939(4) -0.1830(3) 0.8000(3) 0.0567(10) Uani 1 1 d . . .
H3A H 0.5981 -0.1996 0.7756 0.068 Uiso 1 1 calc R . .
C4 C 0.7551(4) -0.0749(3) 0.8332(3) 0.0463(8) Uani 1 1 d . . .
C5 C 0.8959(4) -0.0507(3) 0.8661(4) 0.0655(11) Uani 1 1 d . . .
H5A H 0.9362 0.0231 0.8853 0.079 Uiso 1 1 calc R . .
C6 C 0.9791(4) -0.1310(4) 0.8716(4) 0.0666(12) Uani 1 1 d . . .
H6B H 1.0748 -0.1133 0.8962 0.080 Uiso 1 1 calc R . .
C7 C 0.5932(4) 0.1149(3) 0.9325(3) 0.0466(8) Uani 1 1 d . . .
C8 C 0.5276(3) 0.1328(3) 0.8196(3) 0.0391(7) Uani 1 1 d . . .
C9 C 0.5858(3) 0.0638(3) 0.7654(3) 0.0379(7) Uani 1 1 d . . .
C10 C 0.5826(5) 0.1694(4) 1.0309(3) 0.0663(12) Uani 1 1 d . . .
H10A H 0.6408 0.1380 1.0940 0.100 Uiso 1 1 calc R . .
H10B H 0.4884 0.1568 1.0277 0.100 Uiso 1 1 calc R . .
H10C H 0.6116 0.2483 1.0339 0.100 Uiso 1 1 calc R . .
C11 C 0.4259(3) 0.2026(3) 0.7658(3) 0.0373(7) Uani 1 1 d . . .
C12 C 0.3586(3) 0.2605(3) 0.8295(2) 0.0390(7) Uani 1 1 d . . .
C13 C 0.2668(4) 0.2012(3) 0.8715(3) 0.0532(9) Uani 1 1 d . . .
H13A H 0.2499 0.1237 0.8627 0.064 Uiso 1 1 calc R . .
C14 C 0.2009(4) 0.2583(4) 0.9265(3) 0.0658(12) Uani 1 1 d . . .
H14A H 0.1346 0.2194 0.9495 0.079 Uiso 1 1 calc R . .
C15 C 0.2329(5) 0.3706(4) 0.9466(4) 0.0724(13) Uani 1 1 d . . .
H15A H 0.1903 0.4075 0.9855 0.087 Uiso 1 1 calc R . .
C16 C 0.3280(5) 0.4315(4) 0.9102(3) 0.0685(12) Uani 1 1 d . . .
H16A H 0.3500 0.5083 0.9254 0.082 Uiso 1 1 calc R . .
C17 C 0.3901(4) 0.3767(3) 0.8508(3) 0.0513(9) Uani 1 1 d . . .
H17A H 0.4528 0.4171 0.8251 0.062 Uiso 1 1 calc R . .
C18 C 0.2940(3) 0.2810(3) 0.5999(3) 0.0372(7) Uani 1 1 d . . .
C19 C 0.1672(3) 0.2897(3) 0.6113(3) 0.0450(8) Uani 1 1 d . . .
H19A H 0.1441 0.2537 0.6653 0.054 Uiso 1 1 calc R . .
C20 C 0.0759(4) 0.3535(3) 0.5401(3) 0.0499(9) Uani 1 1 d . . .
H20A H -0.0090 0.3593 0.5467 0.060 Uiso 1 1 calc R . .
C21 C 0.1091(4) 0.4077(3) 0.4603(3) 0.0517(9) Uani 1 1 d . . .
H21A H 0.0490 0.4527 0.4159 0.062 Uiso 1 1 calc R . .
C22 C 0.2331(4) 0.3951(3) 0.4459(3) 0.0452(8) Uani 1 1 d . . .
H22A H 0.2545 0.4294 0.3905 0.054 Uiso 1 1 calc R . .
C23 C 0.3233(3) 0.3316(2) 0.5146(2) 0.0356(7) Uani 1 1 d . . .
C24 C 0.5024(3) 0.3543(3) 0.4395(2) 0.0372(7) Uani 1 1 d . . .
H24A H 0.4692 0.4198 0.4118 0.045 Uiso 1 1 calc R . .
C25 C 0.6100(3) 0.3190(3) 0.4099(2) 0.0370(7) Uani 1 1 d . . .
C26 C 0.6582(4) 0.3858(3) 0.3407(3) 0.0450(8) Uani 1 1 d . . .
H26A H 0.6286 0.4553 0.3242 0.054 Uiso 1 1 calc R . .
C27 C 0.7478(4) 0.3494(3) 0.2979(3) 0.0531(9) Uani 1 1 d . . .
H27A H 0.7794 0.3942 0.2527 0.064 Uiso 1 1 calc R . .
C28 C 0.7923(4) 0.2455(3) 0.3213(3) 0.0511(9) Uani 1 1 d . . .
H28A H 0.8530 0.2212 0.2912 0.061 Uiso 1 1 calc R . .
C29 C 0.7476(3) 0.1780(3) 0.3888(3) 0.0414(7) Uani 1 1 d . . .
C30 C 0.6568(3) 0.2133(3) 0.4366(2) 0.0358(7) Uani 1 1 d . . .
C31 C 0.8735(5) 0.0324(4) 0.3697(4) 0.0712(13) Uani 1 1 d . . .
H31A H 0.8932 -0.0398 0.3958 0.107 Uiso 1 1 calc R . .
H31B H 0.9583 0.0824 0.3881 0.107 Uiso 1 1 calc R . .
H31C H 0.8282 0.0258 0.2930 0.107 Uiso 1 1 calc R . .
C32 C 0.8267(5) 0.3773(5) 0.8234(5) 0.113(2) Uani 1 1 d . . .
H32A H 0.8374 0.4497 0.8582 0.170 Uiso 1 1 calc R . .
H32B H 0.9004 0.3735 0.7963 0.170 Uiso 1 1 calc R . .
H32C H 0.8295 0.3209 0.8741 0.170 Uiso 1 1 calc R . .
C33 C 0.6903(4) 0.3581(3) 0.7316(3) 0.0495(9) Uani 1 1 d . . .
H6C H 0.3777 0.0590 0.4257 0.076(14) Uiso 1 1 d R . .
H6D H 0.2641 0.0702 0.4328 0.098(17) Uiso 1 1 d R . .
H7D H 0.8736 0.0751 0.6600 0.118 Uiso 1 1 d R . .
H7C H 0.8210 0.1625 0.6520 0.118 Uiso 1 1 d R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N4 1.883(3) . ?
Co1 O5 1.885(2) . ?
Co1 O2 1.904(2) . ?
Co1 N3 1.930(3) . ?
Co1 O1 1.955(2) . ?
Co1 O6 1.971(2) . ?
Cl1 C1 1.735(4) . ?
O1 C9 1.294(4) . ?
O2 C30 1.317(4) . ?
O3 C29 1.375(4) . ?
O3 C31 1.409(4) . ?
O4 C33 1.239(4) . ?
O5 C33 1.289(4) . ?
N1 C9 1.353(4) . ?
N1 C4 1.422(4) . ?
N1 N2 1.422(4) . ?
N2 C7 1.309(4) . ?
N3 C11 1.311(4) . ?
N3 C18 1.427(4) . ?
N4 C24 1.297(4) . ?
N4 C23 1.432(4) . ?
C1 C2 1.384(6) . ?
C1 C6 1.395(6) . ?
C2 C3 1.383(5) . ?
C3 C4 1.376(5) . ?
C4 C5 1.368(5) . ?
C5 C6 1.362(5) . ?
C7 C8 1.445(5) . ?
C7 C10 1.502(5) . ?
C8 C9 1.412(4) . ?
C8 C11 1.430(4) . ?
C11 C12 1.489(4) . ?
C12 C13 1.399(5) . ?
C12 C17 1.403(5) . ?
C13 C14 1.391(5) . ?
C14 C15 1.357(6) . ?
C15 C16 1.388(7) . ?
C16 C17 1.388(5) . ?
C18 C19 1.397(4) . ?
C18 C23 1.402(4) . ?
C19 C20 1.400(5) . ?
C20 C21 1.376(6) . ?
C21 C22 1.395(5) . ?
C22 C23 1.376(4) . ?
C24 C25 1.418(4) . ?
C25 C26 1.413(5) . ?
C25 C30 1.425(4) . ?
C26 C27 1.361(5) . ?
C27 C28 1.391(5) . ?
C28 C29 1.380(5) . ?
C29 C30 1.413(4) . ?
C32 C33 1.503(6) . ?

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
N4 Co1 O5 95.71(10) . . ?
N4 Co1 O2 94.14(10) . . ?
O5 Co1 O2 88.10(10) . . ?
N4 Co1 N3 84.69(10) . . ?
O5 Co1 N3 93.00(10) . . ?
O2 Co1 N3 178.46(10) . . ?
N4 Co1 O1 177.52(10) . . ?
O5 Co1 O1 86.46(9) . . ?
O2 Co1 O1 87.12(9) . . ?
N3 Co1 O1 94.02(10) . . ?
N4 Co1 O6 89.19(10) . . ?
O5 Co1 O6 173.83(9) . . ?
O2 Co1 O6 87.81(10) . . ?
N3 Co1 O6 91.18(10) . . ?
O1 Co1 O6 88.72(9) . . ?
C9 O1 Co1 113.52(18) . . ?
C30 O2 Co1 124.6(2) . . ?
C29 O3 C31 117.3(3) . . ?
C33 O5 Co1 130.6(2) . . ?
C9 N1 C4 130.7(3) . . ?
C9 N1 N2 111.6(3) . . ?
C4 N1 N2 117.6(3) . . ?
C7 N2 N1 105.5(3) . . ?
C11 N3 C18 124.7(3) . . ?
C11 N3 Co1 124.7(2) . . ?
C18 N3 Co1 109.74(19) . . ?
C24 N4 C23 122.7(3) . . ?
C24 N4 Co1 125.4(2) . . ?
C23 N4 Co1 111.83(19) . . ?
C2 C1 C6 121.2(4) . . ?
C2 C1 Cl1 119.7(3) . . ?
C6 C1 Cl1 119.0(3) . . ?
C3 C2 C1 118.7(4) . . ?
C4 C3 C2 120.5(4) . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 N1 120.3(3) . . ?
C3 C4 N1 120.1(3) . . ?
C6 C5 C4 122.3(4) . . ?
C5 C6 C1 117.9(4) . . ?
N2 C7 C8 111.2(3) . . ?
N2 C7 C10 117.6(3) . . ?
C8 C7 C10 131.0(3) . . ?
C9 C8 C11 123.4(3) . . ?
C9 C8 C7 105.3(3) . . ?
C11 C8 C7 131.3(3) . . ?
O1 C9 N1 122.3(3) . . ?
O1 C9 C8 131.4(3) . . ?
N1 C9 C8 106.3(3) . . ?
N3 C11 C8 119.7(3) . . ?
N3 C11 C12 121.6(3) . . ?
C8 C11 C12 118.7(3) . . ?
C13 C12 C17 118.8(3) . . ?
C13 C12 C11 121.5(3) . . ?
C17 C12 C11 119.7(3) . . ?
C14 C13 C12 120.0(4) . . ?
C15 C14 C13 120.2(4) . . ?
C14 C15 C16 121.2(4) . . ?
C15 C16 C17 119.4(4) . . ?
C16 C17 C12 120.2(4) . . ?
C19 C18 C23 119.3(3) . . ?
C19 C18 N3 126.3(3) . . ?
C23 C18 N3 114.2(3) . . ?
C18 C19 C20 118.7(3) . . ?
C21 C20 C19 121.3(3) . . ?
C20 C21 C22 119.9(3) . . ?
C23 C22 C21 119.4(3) . . ?
C22 C23 C18 121.2(3) . . ?
C22 C23 N4 124.8(3) . . ?
C18 C23 N4 113.8(3) . . ?
N4 C24 C25 125.5(3) . . ?
C26 C25 C24 117.7(3) . . ?
C26 C25 C30 119.9(3) . . ?
C24 C25 C30 122.0(3) . . ?
C27 C26 C25 120.5(3) . . ?
C26 C27 C28 120.4(3) . . ?
C29 C28 C27 120.8(3) . . ?
O3 C29 C28 125.0(3) . . ?
O3 C29 C30 114.2(3) . . ?
C28 C29 C30 120.8(3) . . ?
O2 C30 C29 117.6(3) . . ?
O2 C30 C25 124.7(3) . . ?
C29 C30 C25 117.6(3) . . ?
O4 C33 O5 127.1(3) . . ?
O4 C33 C32 121.0(4) . . ?
O5 C33 C32 111.9(4) . . ?

_diffrn_measured_fraction_theta_max 0.922
_diffrn_reflns_theta_full        27.21
_diffrn_measured_fraction_theta_full 0.922
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.076
_database_code_depnum_ccdc_archive 'CCDC 1013801'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ldf

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H33 Br Cl Co N4 O7'
_chemical_formula_weight         795.94

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   12.3260(15)
_cell_length_b                   12.7391(15)
_cell_length_c                   13.0205(16)
_cell_angle_alpha                62.534(2)
_cell_angle_beta                 82.794(2)
_cell_angle_gamma                79.008(2)
_cell_volume                     1779.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      1.82
_cell_measurement_theta_max      26.06

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             812
_exptl_absorpt_coefficient_mu    1.733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.599
_exptl_absorpt_correction_T_max  0.695
_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_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9352
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0701
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         26.06
_reflns_number_total             6701
_reflns_number_gt                4230
_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)+(0.1141P)²+0.8978P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0004(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6701
_refine_ls_number_parameters     443
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1834
_refine_ls_wR_factor_gt          0.1547
_refine_ls_goodness_of_fit_ref   0.878
_refine_ls_restrained_S_all      0.878
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.81973(5) 0.56265(5) 0.42203(5) 0.0390(2) Uani 1 1 d . . .
Br1 Br 0.71535(6) -0.05746(5) 0.71346(7) 0.0965(3) Uani 1 1 d . . .
Cl1 Cl 1.4205(2) 0.3698(3) 0.14580(19) 0.1600(13) Uani 1 1 d . . .
O2 O 0.8965(2) 0.4063(3) 0.4843(3) 0.0453(7) Uani 1 1 d . . .
O1 O 0.9568(2) 0.6055(3) 0.3367(2) 0.0430(7) Uani 1 1 d . . .
O6 O 0.8728(2) 0.5820(3) 0.5468(2) 0.0450(7) Uani 1 1 d . . .
H6A H 0.9222 0.5268 0.5794 0.067 Uiso 1 1 calc R . .
H6B H 0.9239 0.5243 0.5799 0.067 Uiso 1 1 d R . .
N3 N 0.7433(3) 0.7239(3) 0.3620(3) 0.0408(8) Uani 1 1 d . . .
N4 N 0.6888(3) 0.5195(3) 0.5113(3) 0.0396(8) Uani 1 1 d . . .
O3 O 0.7818(3) 0.5421(3) 0.2976(3) 0.0507(8) Uani 1 1 d . . .
C30 C 0.8520(4) 0.3088(4) 0.5414(3) 0.0416(10) Uani 1 1 d . . .
O5 O 1.0314(3) 0.2094(3) 0.5377(3) 0.0579(9) Uani 1 1 d . . .
O4 O 0.6010(3) 0.6204(3) 0.2778(3) 0.0604(9) Uani 1 1 d . . .
C24 C 0.6650(4) 0.4110(4) 0.5665(4) 0.0482(11) Uani 1 1 d . . .
H24A H 0.5945 0.4016 0.6013 0.058 Uiso 1 1 calc R . .
N1 N 1.0246(3) 0.7096(3) 0.1511(3) 0.0554(11) Uani 1 1 d . . .
C23 C 0.6187(4) 0.6218(4) 0.5138(4) 0.0443(10) Uani 1 1 d . . .
C29 C 0.9226(4) 0.1973(4) 0.5700(4) 0.0455(11) Uani 1 1 d . . .
N2 N 0.9929(4) 0.8126(4) 0.0483(3) 0.0633(12) Uani 1 1 d . . .
C27 C 0.7689(5) 0.0923(4) 0.6512(5) 0.0595(13) Uani 1 1 d . . .
C9 C 0.9464(4) 0.6960(4) 0.2365(4) 0.0444(10) Uani 1 1 d . . .
C26 C 0.6982(4) 0.1946(4) 0.6321(4) 0.0588(13) Uani 1 1 d . . .
H26A H 0.6238 0.1915 0.6546 0.071 Uiso 1 1 calc R . .
C11 C 0.7642(4) 0.8109(4) 0.2572(4) 0.0419(10) Uani 1 1 d . . .
C25 C 0.7380(4) 0.3067(4) 0.5776(4) 0.0459(11) Uani 1 1 d . . .
C18 C 0.6505(4) 0.7320(4) 0.4365(4) 0.0427(10) Uani 1 1 d . . .
C12 C 0.6856(4) 0.9234(4) 0.2026(4) 0.0491(11) Uani 1 1 d . . .
C8 C 0.8608(4) 0.7939(4) 0.1912(4) 0.0465(11) Uani 1 1 d . . .
C19 C 0.5950(4) 0.8359(4) 0.4430(4) 0.0529(12) Uani 1 1 d . . .
H19A H 0.6176 0.9097 0.3950 0.063 Uiso 1 1 calc R . .
C7 C 0.8963(4) 0.8620(4) 0.0725(4) 0.0554(13) Uani 1 1 d . . .
C4 C 1.1222(4) 0.6279(4) 0.1518(4) 0.0537(13) Uani 1 1 d . . .
C33 C 0.6881(5) 0.5788(4) 0.2463(4) 0.0526(12) Uani 1 1 d . . .
C28 C 0.8825(4) 0.0909(4) 0.6239(4) 0.0581(13) Uani 1 1 d . . .
H28A H 0.9298 0.0190 0.6421 0.070 Uiso 1 1 calc R . .
C10 C 0.8410(5) 0.9737(5) -0.0225(4) 0.0785(19) Uani 1 1 d . . .
H10A H 0.8880 0.9963 -0.0916 0.118 Uiso 1 1 calc R . .
H10B H 0.8274 1.0369 0.0004 0.118 Uiso 1 1 calc R . .
H10C H 0.7720 0.9597 -0.0372 0.118 Uiso 1 1 calc R . .
C13 C 0.7148(5) 1.0322(5) 0.1808(4) 0.0641(14) Uani 1 1 d . . .
H13A H 0.7827 1.0359 0.2021 0.077 Uiso 1 1 calc R . .
C17 C 0.5844(4) 0.9201(5) 0.1680(5) 0.0614(14) Uani 1 1 d . . .
H17A H 0.5640 0.8474 0.1838 0.074 Uiso 1 1 calc R . .
C16 C 0.5146(5) 1.0257(7) 0.1102(5) 0.085(2) Uani 1 1 d . . .
H16A H 0.4485 1.0239 0.0840 0.102 Uiso 1 1 calc R . .
C21 C 0.4722(5) 0.7194(5) 0.5918(5) 0.0646(14) Uani 1 1 d . . .
H21A H 0.4097 0.7159 0.6407 0.078 Uiso 1 1 calc R . .
C22 C 0.5292(4) 0.6150(5) 0.5910(4) 0.0538(12) Uani 1 1 d . . .
H22A H 0.5077 0.5414 0.6417 0.065 Uiso 1 1 calc R . .
C31 C 1.1063(5) 0.1057(5) 0.5480(6) 0.0715(16) Uani 1 1 d . . .
H31A H 1.1792 0.1263 0.5223 0.107 Uiso 1 1 calc R . .
H31B H 1.0833 0.0745 0.5011 0.107 Uiso 1 1 calc R . .
H31C H 1.1070 0.0463 0.6275 0.107 Uiso 1 1 calc R . .
C1 C 1.3056(7) 0.4693(8) 0.1498(5) 0.096(3) Uani 1 1 d . . .
C5 C 1.1118(6) 0.5185(6) 0.1647(6) 0.089(2) Uani 1 1 d . . .
H5A H 1.0416 0.4980 0.1735 0.107 Uiso 1 1 calc R . .
C20 C 0.5060(4) 0.8274(5) 0.5220(5) 0.0616(14) Uani 1 1 d . . .
H20A H 0.4693 0.8957 0.5273 0.074 Uiso 1 1 calc R . .
C3 C 1.2231(5) 0.6584(5) 0.1412(5) 0.083(2) Uani 1 1 d . . .
H3A H 1.2304 0.7320 0.1362 0.099 Uiso 1 1 calc R . .
C14 C 0.6384(7) 1.1365(5) 0.1257(5) 0.086(2) Uani 1 1 d . . .
H14A H 0.6547 1.2101 0.1126 0.103 Uiso 1 1 calc R . .
C32 C 0.7000(6) 0.5690(7) 0.1336(6) 0.109(3) Uani 1 1 d . . .
H32A H 0.6298 0.5964 0.0979 0.163 Uiso 1 1 calc R . .
H32B H 0.7241 0.4870 0.1491 0.163 Uiso 1 1 calc R . .
H32C H 0.7534 0.6173 0.0825 0.163 Uiso 1 1 calc R . .
C6 C 1.2014(8) 0.4384(7) 0.1649(7) 0.104(3) Uani 1 1 d . . .
H6B H 1.1929 0.3631 0.1752 0.125 Uiso 1 1 calc R . .
C2 C 1.3181(6) 0.5774(7) 0.1378(6) 0.101(3) Uani 1 1 d . . .
H2B H 1.3883 0.5984 0.1275 0.122 Uiso 1 1 calc R . .
C15 C 0.5404(7) 1.1304(7) 0.0911(6) 0.094(2) Uani 1 1 d . . .
H15A H 0.4912 1.2002 0.0538 0.113 Uiso 1 1 calc R . .
C34 C 0.0663(5) 0.8478(4) 0.8207(4) 0.0543(13) Uani 1 1 d . . .
H34A H 0.0395 0.8384 0.8965 0.081 Uiso 1 1 calc R . .
H34B H 0.0142 0.9045 0.7645 0.081 Uiso 1 1 calc R . .
H34C H 0.1363 0.8762 0.8028 0.081 Uiso 1 1 calc R . .
C35 C 0.0782(10) 0.7444(10) 0.8184(7) 0.156(4) Uani 1 1 d . . .
H35A H 0.0075 0.7155 0.8409 0.187 Uiso 1 1 calc R . .
H35B H 0.1298 0.6882 0.8769 0.187 Uiso 1 1 calc R . .
O7 O 0.1152(13) 0.7420(9) 0.7137(10) 0.291(7) Uani 1 1 d . . .
H7A H 0.1171 0.6744 0.7206 0.436 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O2 1.872(3) . ?
Co1 N4 1.880(3) . ?
Co1 O3 1.882(3) . ?
Co1 N3 1.920(4) . ?
Co1 O1 1.925(3) . ?
Co1 O6 1.956(3) . ?
Br1 C27 1.911(5) . ?
Cl1 C1 1.725(7) . ?
O2 C30 1.305(5) . ?
O1 C9 1.282(5) . ?
N3 C11 1.335(5) . ?
N3 C18 1.424(5) . ?
N4 C24 1.303(5) . ?
N4 C23 1.432(6) . ?
O3 C33 1.302(6) . ?
C30 C25 1.426(6) . ?
C30 C29 1.427(6) . ?
O5 C29 1.370(5) . ?
O5 C31 1.420(6) . ?
O4 C33 1.214(6) . ?
C24 C25 1.413(7) . ?
N1 C9 1.346(6) . ?
N1 N2 1.407(5) . ?
N1 C4 1.432(6) . ?
C23 C22 1.383(6) . ?
C23 C18 1.394(6) . ?
C29 C28 1.365(6) . ?
N2 C7 1.309(6) . ?
C27 C26 1.357(7) . ?
C27 C28 1.400(7) . ?
C9 C8 1.412(6) . ?
C26 C25 1.424(6) . ?
C11 C8 1.421(6) . ?
C11 C12 1.484(6) . ?
C18 C19 1.404(6) . ?
C12 C13 1.391(7) . ?
C12 C17 1.392(7) . ?
C8 C7 1.440(6) . ?
C19 C20 1.390(7) . ?
C7 C10 1.496(6) . ?
C4 C3 1.345(8) . ?
C4 C5 1.354(8) . ?
C33 C32 1.516(8) . ?
C13 C14 1.407(8) . ?
C17 C16 1.379(8) . ?
C16 C15 1.333(10) . ?
C21 C20 1.364(7) . ?
C21 C22 1.385(7) . ?
C1 C2 1.349(11) . ?
C1 C6 1.378(12) . ?
C5 C6 1.353(9) . ?
C3 C2 1.417(9) . ?
C14 C15 1.369(10) . ?
C34 C35 1.311(11) . ?
C35 O7 1.394(12) . ?

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
O2 Co1 N4 94.50(14) . . ?
O2 Co1 O3 89.25(13) . . ?
N4 Co1 O3 95.25(14) . . ?
O2 Co1 N3 178.00(14) . . ?
N4 Co1 N3 85.71(15) . . ?
O3 Co1 N3 92.71(14) . . ?
O2 Co1 O1 84.71(12) . . ?
N4 Co1 O1 177.50(14) . . ?
O3 Co1 O1 87.11(13) . . ?
N3 Co1 O1 95.00(13) . . ?
O2 Co1 O6 88.44(13) . . ?
N4 Co1 O6 89.38(14) . . ?
O3 Co1 O6 174.97(13) . . ?
N3 Co1 O6 89.57(14) . . ?
O1 Co1 O6 88.23(12) . . ?
C30 O2 Co1 125.7(3) . . ?
C9 O1 Co1 115.0(3) . . ?
C11 N3 C18 124.7(4) . . ?
C11 N3 Co1 124.3(3) . . ?
C18 N3 Co1 110.2(3) . . ?
C24 N4 C23 123.8(4) . . ?
C24 N4 Co1 125.3(3) . . ?
C23 N4 Co1 111.0(3) . . ?
C33 O3 Co1 128.4(3) . . ?
O2 C30 C25 124.3(4) . . ?
O2 C30 C29 117.5(4) . . ?
C25 C30 C29 118.1(4) . . ?
C29 O5 C31 117.8(4) . . ?
N4 C24 C25 125.0(4) . . ?
C9 N1 N2 111.1(4) . . ?
C9 N1 C4 127.9(4) . . ?
N2 N1 C4 120.6(4) . . ?
C22 C23 C18 120.8(4) . . ?
C22 C23 N4 123.8(4) . . ?
C18 C23 N4 115.2(4) . . ?
C28 C29 O5 124.9(4) . . ?
C28 C29 C30 121.8(4) . . ?
O5 C29 C30 113.3(4) . . ?
C7 N2 N1 106.1(4) . . ?
C26 C27 C28 122.5(5) . . ?
C26 C27 Br1 120.7(4) . . ?
C28 C27 Br1 116.8(4) . . ?
O1 C9 N1 121.4(4) . . ?
O1 C9 C8 131.4(4) . . ?
N1 C9 C8 107.2(4) . . ?
C27 C26 C25 120.0(5) . . ?
N3 C11 C8 119.9(4) . . ?
N3 C11 C12 122.1(4) . . ?
C8 C11 C12 117.9(4) . . ?
C24 C25 C26 119.1(4) . . ?
C24 C25 C30 122.1(4) . . ?
C26 C25 C30 118.7(4) . . ?
C23 C18 C19 119.1(4) . . ?
C23 C18 N3 114.0(4) . . ?
C19 C18 N3 126.8(4) . . ?
C13 C12 C17 120.1(5) . . ?
C13 C12 C11 120.3(4) . . ?
C17 C12 C11 119.5(5) . . ?
C9 C8 C11 123.4(4) . . ?
C9 C8 C7 104.5(4) . . ?
C11 C8 C7 132.1(4) . . ?
C20 C19 C18 119.3(5) . . ?
N2 C7 C8 111.1(4) . . ?
N2 C7 C10 118.0(4) . . ?
C8 C7 C10 130.8(5) . . ?
C3 C4 C5 120.3(6) . . ?
C3 C4 N1 120.6(5) . . ?
C5 C4 N1 119.1(5) . . ?
O4 C33 O3 127.2(5) . . ?
O4 C33 C32 121.5(5) . . ?
O3 C33 C32 111.3(5) . . ?
C29 C28 C27 118.6(5) . . ?
C12 C13 C14 117.9(6) . . ?
C16 C17 C12 119.4(6) . . ?
C15 C16 C17 121.1(6) . . ?
C20 C21 C22 121.2(5) . . ?
C23 C22 C21 119.0(5) . . ?
C2 C1 C6 120.3(6) . . ?
C2 C1 Cl1 119.7(8) . . ?
C6 C1 Cl1 120.0(7) . . ?
C6 C5 C4 121.4(7) . . ?
C21 C20 C19 120.4(5) . . ?
C4 C3 C2 119.3(7) . . ?
C15 C14 C13 120.5(6) . . ?
C5 C6 C1 119.4(7) . . ?
C1 C2 C3 119.3(7) . . ?
C16 C15 C14 120.9(6) . . ?
C34 C35 O7 117.2(9) . . ?

_diffrn_measured_fraction_theta_max 0.950
_diffrn_reflns_theta_full        26.06
_diffrn_measured_fraction_theta_full 0.950
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.074
_database_code_depnum_ccdc_archive 'CCDC 1013802'
