# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2012


data_global
#TrackingRef '- revised crystal structure data.cif'

_journal_name_full               'Dalton Trans.'
_journal_coden_cambridge         0222
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       qhzhao@ynu.edu.cn
_publ_contact_author_name        'Qi-Hua Zhao'
loop_
_publ_author_name
'Zong-Ze Li'
'Lin Du'
'Jie Zhou'
'Ming-Rong Zhu'
'Fen-Hua Qian'
;
Jing Liu
;
'Peng Chen'
'Qi-Hua Zhao'

data_1
#TrackingRef '- revised crystal structure data.cif'

_database_code_depnum_ccdc_archive 'CCDC 872198'
#TrackingRef '- 872198.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 Co N2 O4'
_chemical_formula_weight         396.28

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'

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   I4(1)/a

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   29.1220(15)
_cell_length_b                   29.1220(15)
_cell_length_c                   8.7975(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     7461.1(9)
_cell_formula_units_Z            16
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3264
_exptl_absorpt_coefficient_mu    0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7711
_exptl_absorpt_correction_T_max  0.8483
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  '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            20883
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.40
_diffrn_reflns_theta_max         25.25
_reflns_number_total             3370
_reflns_number_gt                2273
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond 3.1'
_computing_publication_material  'Diamond 3.1'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.1546P)^2^+9.3531P] where P=(Fo^2^+2Fc^2^)/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         3370
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1047
_refine_ls_R_factor_gt           0.0718
_refine_ls_wR_factor_ref         0.2434
_refine_ls_wR_factor_gt          0.2166
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.86215(18) 0.10486(17) 0.2648(6) 0.0570(13) Uani 1 1 d . . .
C2 C 0.8427(2) 0.0592(2) 0.2430(8) 0.0783(19) Uani 1 1 d . . .
H2 H 0.8361 0.0489 0.1454 0.094 Uiso 1 1 calc R . .
C3 C 0.8342(2) 0.0319(2) 0.3631(7) 0.0711(17) Uani 1 1 d . . .
H3 H 0.8217 0.0030 0.3452 0.085 Uiso 1 1 calc R . .
C4 C 0.84338(18) 0.04484(17) 0.5162(7) 0.0572(14) Uani 1 1 d . . .
C5 C 0.8353(2) 0.0147(2) 0.6369(8) 0.0678(16) Uani 1 1 d . . .
H5 H 0.8224 -0.0139 0.6175 0.081 Uiso 1 1 calc R . .
C6 C 0.8460(2) 0.0266(2) 0.7834(8) 0.0743(18) Uani 1 1 d . . .
H6 H 0.8415 0.0062 0.8633 0.089 Uiso 1 1 calc R . .
C7 C 0.8638(2) 0.0699(2) 0.8087(7) 0.0776(17) Uani 1 1 d . . .
H7 H 0.8706 0.0785 0.9079 0.093 Uiso 1 1 calc R . .
C8 C 0.8717(2) 0.10039(19) 0.6956(6) 0.0641(15) Uani 1 1 d . . .
H8 H 0.8837 0.1291 0.7191 0.077 Uiso 1 1 calc R . .
C9 C 0.86192(16) 0.08926(17) 0.5413(6) 0.0510(12) Uani 1 1 d . . .
C10 C 0.87081(17) 0.11962(16) 0.4153(6) 0.0467(11) Uani 1 1 d . . .
C11 C 0.88636(18) 0.16513(17) 0.4446(6) 0.0560(13) Uani 1 1 d . . .
H11A H 0.8631 0.1786 0.5096 0.067 Uiso 1 1 d R . .
C12 C 0.9133(4) 0.2400(2) 0.4085(8) 0.105(3) Uani 1 1 d . . .
H12A H 0.9425 0.2344 0.4554 0.126 Uiso 0.50 1 d PR A .
H12B H 0.8838 0.2516 0.4385 0.126 Uiso 0.50 1 d PR . .
C13 C 0.9369(12) 0.2495(9) 0.557(3) 0.140(15) Uani 0.359(19) 1 d P A 1
H13A H 0.9196 0.2361 0.6381 0.210 Uiso 0.359(19) 1 calc PR A 1
H13B H 0.9390 0.2821 0.5716 0.210 Uiso 0.359(19) 1 calc PR A 1
H13C H 0.9672 0.2365 0.5548 0.210 Uiso 0.359(19) 1 calc PR A 1
C13' C 0.8811(8) 0.2600(4) 0.5313(12) 0.140(10) Uani 0.641(19) 1 d P A 2
H13D H 0.8806 0.2398 0.6175 0.210 Uiso 0.641(19) 1 calc PR A 2
H13E H 0.8507 0.2629 0.4906 0.210 Uiso 0.641(19) 1 calc PR A 2
H13F H 0.8921 0.2896 0.5620 0.210 Uiso 0.641(19) 1 calc PR A 2
C14 C 0.92085(18) 0.27384(18) 0.2782(8) 0.0613(15) Uani 1 1 d . A .
C15 C 0.8377(2) 0.2561(2) -0.0675(10) 0.102(3) Uani 1 1 d . . .
H15 H 0.8609 0.2768 -0.0434 0.122 Uiso 1 1 calc R . .
C16 C 0.8035(3) 0.2710(3) -0.1599(12) 0.124(4) Uani 1 1 d . . .
H16 H 0.8035 0.3012 -0.1945 0.149 Uiso 1 1 calc R . .
C17 C 0.7693(2) 0.2422(3) -0.2018(9) 0.089(2) Uani 1 1 d . . .
C18 C 0.7727(3) 0.1992(2) -0.1444(11) 0.112(3) Uani 1 1 d . . .
H18 H 0.7500 0.1777 -0.1662 0.135 Uiso 1 1 calc R . .
C19 C 0.8085(2) 0.1871(2) -0.0562(10) 0.099(3) Uani 1 1 d . . .
H19 H 0.8103 0.1565 -0.0261 0.119 Uiso 1 1 calc R . .
Co1 Co 0.89579(2) 0.19064(2) 0.11949(7) 0.0510(3) Uani 1 1 d . . .
N1 N 0.89653(16) 0.19644(14) 0.3487(5) 0.0566(11) Uani 1 1 d . A .
N2 N 0.84068(13) 0.21469(14) -0.0096(5) 0.0560(11) Uani 1 1 d . A .
O1 O 0.87073(16) 0.12835(13) 0.1434(4) 0.0690(11) Uani 1 1 d . A .
O2 O 0.91710(13) 0.26010(13) 0.1462(5) 0.0618(10) Uani 1 1 d . A .
O3 O 0.93220(16) 0.31390(13) 0.3169(5) 0.0757(12) Uani 1 1 d . . .
O4 O 0.720(2) 0.258(2) 0.184(6) 0.47(5) Uani 0.50 1 d P B 1
H4A H 0.7010 0.2360 0.1783 0.706 Uiso 0.50 1 d PR B 1
H4B H 0.7176 0.2709 0.2705 0.706 Uiso 0.50 1 d PR B 1
O5 O 0.7455(17) 0.3065(16) 0.181(5) 0.49(5) Uani 0.50 1 d P C 2
H5A H 0.7208 0.2909 0.1776 0.732 Uiso 0.50 1 d PR C 2
H5C H 0.7453 0.3263 0.1099 0.732 Uiso 0.50 1 d PR C 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.062(3) 0.047(3) 0.062(3) -0.001(3) -0.006(3) 0.002(2)
C2 0.102(5) 0.058(3) 0.075(4) -0.003(3) -0.019(4) -0.020(3)
C3 0.087(4) 0.044(3) 0.082(5) -0.003(3) -0.001(3) -0.018(3)
C4 0.058(3) 0.043(3) 0.071(4) 0.007(3) 0.007(3) 0.000(2)
C5 0.064(4) 0.048(3) 0.092(5) 0.000(3) 0.017(3) 0.000(3)
C6 0.092(5) 0.063(4) 0.068(4) 0.018(3) 0.028(3) 0.005(3)
C7 0.093(5) 0.083(4) 0.057(4) 0.002(3) 0.015(3) -0.010(4)
C8 0.084(4) 0.054(3) 0.055(3) 0.002(3) 0.015(3) -0.008(3)
C9 0.049(3) 0.049(3) 0.055(3) -0.004(2) 0.003(2) 0.005(2)
C10 0.050(3) 0.040(2) 0.050(3) 0.001(2) 0.001(2) 0.001(2)
C11 0.061(3) 0.049(3) 0.058(3) -0.003(3) 0.004(3) -0.001(2)
C12 0.209(10) 0.056(4) 0.051(4) -0.005(3) 0.006(5) -0.063(5)
C13 0.20(3) 0.13(2) 0.088(17) 0.044(15) 0.09(2) 0.09(2)
C13' 0.31(3) 0.051(7) 0.054(7) -0.005(5) 0.006(10) -0.067(11)
C14 0.064(3) 0.051(3) 0.069(4) 0.009(3) -0.002(3) -0.011(3)
C15 0.084(4) 0.062(4) 0.159(7) 0.059(4) -0.060(5) -0.046(3)
C16 0.087(5) 0.077(5) 0.209(10) 0.064(6) -0.085(6) -0.041(4)
C17 0.070(4) 0.099(5) 0.099(6) 0.005(4) -0.006(4) -0.001(4)
C18 0.097(5) 0.049(3) 0.190(9) 0.032(4) -0.099(6) -0.025(3)
C19 0.092(5) 0.041(3) 0.164(7) 0.019(4) -0.064(5) -0.005(3)
Co1 0.0557(5) 0.0471(5) 0.0501(5) 0.0025(3) -0.0066(3) 0.0025(3)
N1 0.073(3) 0.041(2) 0.055(3) -0.0017(19) -0.004(2) -0.006(2)
N2 0.042(2) 0.052(2) 0.074(3) 0.008(2) -0.007(2) -0.0006(18)
O1 0.103(3) 0.048(2) 0.056(2) 0.0046(18) -0.016(2) -0.009(2)
O2 0.066(2) 0.057(2) 0.062(3) 0.0103(18) -0.0052(18) -0.0091(18)
O3 0.097(3) 0.044(2) 0.086(3) 0.003(2) -0.003(2) -0.024(2)
O4 0.68(13) 0.38(5) 0.35(7) -0.02(5) 0.37(8) 0.11(7)
O5 0.65(9) 0.48(7) 0.34(5) -0.21(5) 0.10(5) -0.36(7)

_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 O1 1.292(6) . ?
C1 C10 1.415(8) . ?
C1 C2 1.457(7) . ?
C2 C3 1.347(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.424(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.397(8) . ?
C4 C9 1.419(7) . ?
C5 C6 1.371(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.380(9) . ?
C6 H6 0.9300 . ?
C7 C8 1.353(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.425(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.441(7) . ?
C10 C11 1.424(7) . ?
C11 N1 1.277(7) . ?
C11 H11A 0.9700 . ?
C12 N1 1.458(7) . ?
C12 C13 1.50(4) . ?
C12 C14 1.527(8) . ?
C12 C13' 1.544(19) . ?
C12 H12A 0.9597 . ?
C12 H12B 0.9603 . ?
C13 H12A 1.0064 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C13' H12B 0.8546 . ?
C13' H13D 0.9600 . ?
C13' H13E 0.9600 . ?
C13' H13F 0.9600 . ?
C14 O2 1.233(7) . ?
C14 O3 1.260(6) . ?
C15 N2 1.311(7) . ?
C15 C16 1.359(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.352(9) . ?
C16 H16 0.9300 . ?
C17 C18 1.356(9) . ?
C17 C17 1.477(14) 13_654 ?
C18 C19 1.346(8) . ?
C18 H18 0.9300 . ?
C19 N2 1.302(7) . ?
C19 H19 0.9300 . ?
Co1 O1 1.967(4) . ?
Co1 N1 2.024(5) . ?
Co1 O3 2.032(4) 12_756 ?
Co1 N2 2.087(4) . ?
Co1 O2 2.129(4) . ?
O3 Co1 2.032(4) 15_665 ?
O4 H4A 0.8500 . ?
O4 H4B 0.8500 . ?
O4 H5A 0.9628 . ?
O5 H5A 0.8499 . ?
O5 H5C 0.8500 . ?

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
O1 C1 C10 125.3(5) . . ?
O1 C1 C2 116.7(5) . . ?
C10 C1 C2 118.0(5) . . ?
C3 C2 C1 120.6(6) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 123.4(5) . . ?
C2 C3 H3 118.3 . . ?
C4 C3 H3 118.3 . . ?
C5 C4 C9 121.2(6) . . ?
C5 C4 C3 121.4(5) . . ?
C9 C4 C3 117.4(5) . . ?
C6 C5 C4 121.2(6) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 117.9(6) . . ?
C5 C6 H6 121.1 . . ?
C7 C6 H6 121.1 . . ?
C8 C7 C6 123.0(6) . . ?
C8 C7 H7 118.5 . . ?
C6 C7 H7 118.5 . . ?
C7 C8 C9 121.2(6) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C4 C9 C8 115.6(5) . . ?
C4 C9 C10 120.5(5) . . ?
C8 C9 C10 123.9(5) . . ?
C1 C10 C11 120.6(5) . . ?
C1 C10 C9 120.1(4) . . ?
C11 C10 C9 119.3(5) . . ?
N1 C11 C10 128.2(5) . . ?
N1 C11 H11A 105.2 . . ?
C10 C11 H11A 105.2 . . ?
N1 C12 C13 128.9(11) . . ?
N1 C12 C14 109.8(5) . . ?
C13 C12 C14 117.8(12) . . ?
N1 C12 C13' 112.1(7) . . ?
C13 C12 C13' 66.4(10) . . ?
C14 C12 C13' 111.7(7) . . ?
N1 C12 H12A 107.8 . . ?
C13 C12 H12A 41.5 . . ?
C14 C12 H12A 107.8 . . ?
C13' C12 H12A 107.5 . . ?
N1 C12 H12B 96.1 . . ?
C13 C12 H12B 96.0 . . ?
C14 C12 H12B 96.1 . . ?
C13' C12 H12B 29.7 . . ?
H12A C12 H12B 137.2 . . ?
C12 C13 H12A 39.2 . . ?
C12 C13 H13A 109.5 . . ?
H12A C13 H13A 124.6 . . ?
C12 C13 H13B 109.5 . . ?
H12A C13 H13B 123.0 . . ?
C12 C13 H13C 109.5 . . ?
H12A C13 H13C 70.3 . . ?
C12 C13' H12B 33.8 . . ?
C12 C13' H13D 109.5 . . ?
H12B C13' H13D 125.7 . . ?
C12 C13' H13E 109.5 . . ?
H12B C13' H13E 75.8 . . ?
H13D C13' H13E 109.5 . . ?
C12 C13' H13F 109.5 . . ?
H12B C13' H13F 119.6 . . ?
H13D C13' H13F 109.5 . . ?
H13E C13' H13F 109.5 . . ?
O2 C14 O3 125.3(5) . . ?
O2 C14 C12 119.0(5) . . ?
O3 C14 C12 115.6(6) . . ?
N2 C15 C16 125.0(5) . . ?
N2 C15 H15 117.5 . . ?
C16 C15 H15 117.5 . . ?
C17 C16 C15 120.5(6) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 114.7(6) . . ?
C16 C17 C17 121.8(9) . 13_654 ?
C18 C17 C17 123.5(8) . 13_654 ?
C19 C18 C17 120.9(6) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
N2 C19 C18 125.3(6) . . ?
N2 C19 H19 117.3 . . ?
C18 C19 H19 117.3 . . ?
O1 Co1 N1 88.53(16) . . ?
O1 Co1 O3 100.91(19) . 12_756 ?
N1 Co1 O3 143.93(18) . 12_756 ?
O1 Co1 N2 94.72(16) . . ?
N1 Co1 N2 121.47(19) . . ?
O3 Co1 N2 92.63(17) 12_756 . ?
O1 Co1 O2 166.61(17) . . ?
N1 Co1 O2 78.91(16) . . ?
O3 Co1 O2 92.03(17) 12_756 . ?
N2 Co1 O2 88.00(16) . . ?
C11 N1 C12 117.4(5) . . ?
C11 N1 Co1 126.6(4) . . ?
C12 N1 Co1 115.8(4) . . ?
C19 N2 C15 113.5(5) . . ?
C19 N2 Co1 121.2(4) . . ?
C15 N2 Co1 124.7(4) . . ?
C1 O1 Co1 130.4(3) . . ?
C14 O2 Co1 116.0(3) . . ?
C14 O3 Co1 110.4(4) . 15_665 ?
H4A O4 H4B 109.5 . . ?
H4A O4 H5A 139.5 . . ?
H4B O4 H5A 67.3 . . ?
H5A O5 H5C 109.5 . . ?

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
O1 C1 C2 C3 177.7(6) . . . . ?
C10 C1 C2 C3 -1.3(9) . . . . ?
C1 C2 C3 C4 -0.2(11) . . . . ?
C2 C3 C4 C5 -178.0(6) . . . . ?
C2 C3 C4 C9 0.8(10) . . . . ?
C9 C4 C5 C6 -1.7(9) . . . . ?
C3 C4 C5 C6 177.1(6) . . . . ?
C4 C5 C6 C7 2.0(9) . . . . ?
C5 C6 C7 C8 -1.2(10) . . . . ?
C6 C7 C8 C9 0.0(10) . . . . ?
C5 C4 C9 C8 0.4(7) . . . . ?
C3 C4 C9 C8 -178.5(5) . . . . ?
C5 C4 C9 C10 178.9(5) . . . . ?
C3 C4 C9 C10 0.1(8) . . . . ?
C7 C8 C9 C4 0.4(8) . . . . ?
C7 C8 C9 C10 -178.1(6) . . . . ?
O1 C1 C10 C11 6.1(8) . . . . ?
C2 C1 C10 C11 -175.0(5) . . . . ?
O1 C1 C10 C9 -176.8(5) . . . . ?
C2 C1 C10 C9 2.1(8) . . . . ?
C4 C9 C10 C1 -1.6(7) . . . . ?
C8 C9 C10 C1 176.8(5) . . . . ?
C4 C9 C10 C11 175.6(4) . . . . ?
C8 C9 C10 C11 -6.0(8) . . . . ?
C1 C10 C11 N1 -3.9(9) . . . . ?
C9 C10 C11 N1 179.0(5) . . . . ?
N1 C12 C14 O2 -7.4(10) . . . . ?
C13 C12 C14 O2 153.7(12) . . . . ?
C13' C12 C14 O2 -132.4(9) . . . . ?
N1 C12 C14 O3 175.0(6) . . . . ?
C13 C12 C14 O3 -23.9(14) . . . . ?
C13' C12 C14 O3 50.0(11) . . . . ?
N2 C15 C16 C17 -1.4(18) . . . . ?
C15 C16 C17 C18 0.1(15) . . . . ?
C15 C16 C17 C17 178.1(11) . . . 13_654 ?
C16 C17 C18 C19 -1.6(15) . . . . ?
C17 C17 C18 C19 -179.5(11) 13_654 . . . ?
C17 C18 C19 N2 4.7(17) . . . . ?
C10 C11 N1 C12 -177.8(7) . . . . ?
C10 C11 N1 Co1 -2.2(8) . . . . ?
C13 C12 N1 C11 25.0(17) . . . . ?
C14 C12 N1 C11 -176.6(6) . . . . ?
C13' C12 N1 C11 -51.9(11) . . . . ?
C13 C12 N1 Co1 -151.1(14) . . . . ?
C14 C12 N1 Co1 7.3(9) . . . . ?
C13' C12 N1 Co1 132.0(8) . . . . ?
O1 Co1 N1 C11 4.6(5) . . . . ?
O3 Co1 N1 C11 -102.1(5) 12_756 . . . ?
N2 Co1 N1 C11 99.2(5) . . . . ?
O2 Co1 N1 C11 179.9(5) . . . . ?
O1 Co1 N1 C12 -179.8(5) . . . . ?
O3 Co1 N1 C12 73.6(6) 12_756 . . . ?
N2 Co1 N1 C12 -85.1(6) . . . . ?
O2 Co1 N1 C12 -4.4(5) . . . . ?
C18 C19 N2 C15 -5.6(14) . . . . ?
C18 C19 N2 Co1 -177.4(8) . . . . ?
C16 C15 N2 C19 3.9(14) . . . . ?
C16 C15 N2 Co1 175.4(9) . . . . ?
O1 Co1 N2 C19 -6.9(6) . . . . ?
N1 Co1 N2 C19 -98.1(6) . . . . ?
O3 Co1 N2 C19 94.3(6) 12_756 . . . ?
O2 Co1 N2 C19 -173.8(6) . . . . ?
O1 Co1 N2 C15 -177.7(6) . . . . ?
N1 Co1 N2 C15 91.1(7) . . . . ?
O3 Co1 N2 C15 -76.6(7) 12_756 . . . ?
O2 Co1 N2 C15 15.4(7) . . . . ?
C10 C1 O1 Co1 -2.0(8) . . . . ?
C2 C1 O1 Co1 179.1(4) . . . . ?
N1 Co1 O1 C1 -2.6(5) . . . . ?
O3 Co1 O1 C1 142.3(5) 12_756 . . . ?
N2 Co1 O1 C1 -124.1(5) . . . . ?
O2 Co1 O1 C1 -22.7(11) . . . . ?
O3 C14 O2 Co1 -178.7(4) . . . . ?
C12 C14 O2 Co1 4.0(8) . . . . ?
O1 Co1 O2 C14 20.7(9) . . . . ?
N1 Co1 O2 C14 0.2(4) . . . . ?
O3 Co1 O2 C14 -144.6(4) 12_756 . . . ?
N2 Co1 O2 C14 122.8(4) . . . . ?
O2 C14 O3 Co1 2.7(7) . . . 15_665 ?
C12 C14 O3 Co1 -179.9(5) . . . 15_665 ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.060
_refine_diff_density_min         -0.853
_refine_diff_density_rms         0.087

_publ_section_exptl_refinement   
;
H atoms bonded to water molecules atom were located in a difference map. H atoms
were calculated geometrically and allowed to ride on the C atoms to which they are bonded.
In complex 1, the CCH3 (C13) group and water molecules displayed elongated displacement
ellipsoids. We attempted to split the C13 atom and water molecules and re-refined the related
data. The disordered system model improved the quality of the refinement. The disordered
atoms are realistic and need not to severely be restrained using other
commands (SHELXL 97; Sheldrick, 2008).
;

data_2
#TrackingRef '- revised crystal structure data.cif'

_database_code_depnum_ccdc_archive 'CCDC 872199'
#TrackingRef '- 872199.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 Co N2 O3'
_chemical_formula_weight         364.23

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   12.173(2)
_cell_length_b                   6.6055(12)
_cell_length_c                   19.308(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.017(3)
_cell_angle_gamma                90.00
_cell_volume                     1551.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    1.124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7663
_exptl_absorpt_correction_T_max  0.8769
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  '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            10142
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_av_sigmaI/netI    0.0913
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         28.40
_reflns_number_total             3661
_reflns_number_gt                2078
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond 3.1'
_computing_publication_material  'Diamond 3.1'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0360P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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         3661
_refine_ls_number_parameters     217
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1105
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1128
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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 -0.10877(4) 0.97630(7) 0.21805(2) 0.03559(17) Uani 1 1 d . . .
O1 O 0.0070(2) 0.7758(3) 0.20673(11) 0.0411(6) Uani 1 1 d . . .
O2 O -0.2258(2) 1.1936(3) 0.25532(11) 0.0389(6) Uani 1 1 d . . .
O3 O -0.2688(2) 1.3738(4) 0.34760(12) 0.0416(7) Uani 1 1 d . . .
N1 N -0.0575(2) 1.0093(4) 0.31768(14) 0.0377(7) Uani 1 1 d . . .
N2 N -0.0596(2) 1.1819(4) 0.14276(14) 0.0354(7) Uani 1 1 d . . .
C1 C 0.0555(3) 0.6651(5) 0.25374(18) 0.0358(9) Uani 1 1 d . . .
C2 C 0.1112(3) 0.4867(5) 0.23220(19) 0.0409(9) Uani 1 1 d . . .
H2A H 0.1129 0.4579 0.1851 0.049 Uiso 1 1 calc R . .
C3 C 0.1610(3) 0.3593(6) 0.2771(2) 0.0484(10) Uani 1 1 d . . .
H3A H 0.1945 0.2437 0.2603 0.058 Uiso 1 1 calc R . .
C4 C 0.1643(3) 0.3953(6) 0.3496(2) 0.0451(10) Uani 1 1 d . . .
C5 C 0.2138(4) 0.2560(7) 0.3962(2) 0.0684(14) Uani 1 1 d . . .
H5A H 0.2441 0.1375 0.3792 0.082 Uiso 1 1 calc R . .
C6 C 0.2182(4) 0.2917(8) 0.4655(2) 0.0803(16) Uani 1 1 d . . .
H6A H 0.2524 0.1996 0.4956 0.096 Uiso 1 1 calc R . .
C7 C 0.1716(4) 0.4651(8) 0.4909(2) 0.0808(17) Uani 1 1 d . . .
H7A H 0.1742 0.4889 0.5384 0.097 Uiso 1 1 calc R . .
C8 C 0.1212(4) 0.6041(7) 0.4470(2) 0.0678(14) Uani 1 1 d . . .
H8A H 0.0909 0.7204 0.4656 0.081 Uiso 1 1 calc R . .
C9 C 0.1145(3) 0.5740(6) 0.37429(19) 0.0429(10) Uani 1 1 d . . .
C10 C 0.0578(3) 0.7090(5) 0.32613(18) 0.0366(9) Uani 1 1 d D . .
C11 C 0.0025(3) 0.8830(5) 0.35211(18) 0.0413(9) Uani 1 1 d D . .
H11A H 0.0111 0.9069 0.3995 0.050 Uiso 1 1 calc R . .
C12 C -0.1066(3) 1.1767(5) 0.35524(19) 0.0454(10) Uani 1 1 d . . .
H12A H -0.0537 1.2859 0.3607 0.054 Uiso 1 1 calc R . .
H12B H -0.1259 1.1315 0.4010 0.054 Uiso 1 1 calc R . .
C13 C -0.2076(3) 1.2524(5) 0.31648(18) 0.0357(9) Uani 1 1 d . . .
C14 C -0.1094(3) 1.3607(5) 0.13252(18) 0.0383(9) Uani 1 1 d . . .
H14A H -0.1616 1.4009 0.1638 0.046 Uiso 1 1 calc R . .
C15 C -0.0876(3) 1.4883(5) 0.07853(17) 0.0373(9) Uani 1 1 d . . .
H15A H -0.1243 1.6115 0.0743 0.045 Uiso 1 1 calc R . .
C16 C -0.0114(3) 1.4342(5) 0.03038(17) 0.0336(8) Uani 1 1 d . . .
C17 C 0.0414(3) 1.2510(6) 0.0419(2) 0.0538(12) Uani 1 1 d . . .
H17A H 0.0948 1.2084 0.0118 0.065 Uiso 1 1 calc R . .
C18 C 0.0158(3) 1.1317(6) 0.0972(2) 0.0497(11) Uani 1 1 d . . .
H18A H 0.0528 1.0095 0.1033 0.060 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Co1 0.0433(3) 0.0354(3) 0.0281(3) -0.0002(2) 0.0016(2) 0.0002(3)
O1 0.0530(17) 0.0372(14) 0.0332(14) 0.0003(11) 0.0019(12) 0.0088(13)
O2 0.0436(16) 0.0427(15) 0.0302(13) -0.0030(12) 0.0004(12) 0.0019(12)
O3 0.0462(17) 0.0430(15) 0.0362(14) -0.0030(12) 0.0070(12) 0.0132(13)
N1 0.0423(19) 0.0360(18) 0.0345(16) -0.0055(14) -0.0022(14) 0.0066(15)
N2 0.0417(19) 0.0289(16) 0.0362(17) -0.0017(13) 0.0076(14) -0.0017(14)
C1 0.033(2) 0.036(2) 0.039(2) -0.0010(17) 0.0081(17) -0.0041(17)
C2 0.039(2) 0.040(2) 0.045(2) -0.0066(19) 0.0066(18) 0.0010(19)
C3 0.044(3) 0.039(2) 0.062(3) -0.005(2) 0.002(2) 0.011(2)
C4 0.043(2) 0.051(2) 0.041(2) -0.001(2) -0.0010(19) 0.009(2)
C5 0.076(4) 0.064(3) 0.065(3) 0.004(3) -0.006(3) 0.034(3)
C6 0.085(4) 0.094(4) 0.061(3) 0.013(3) -0.014(3) 0.042(3)
C7 0.102(4) 0.097(4) 0.042(3) -0.006(3) -0.015(3) 0.044(3)
C8 0.092(4) 0.067(3) 0.043(3) -0.008(2) -0.014(2) 0.034(3)
C9 0.042(2) 0.045(2) 0.041(2) -0.0044(18) -0.0037(19) 0.0102(19)
C10 0.034(2) 0.037(2) 0.039(2) -0.0064(17) -0.0007(17) 0.0057(17)
C11 0.047(2) 0.048(2) 0.029(2) -0.0063(18) -0.0056(18) 0.007(2)
C12 0.045(3) 0.046(2) 0.045(2) -0.0111(19) -0.0057(19) 0.012(2)
C13 0.043(2) 0.028(2) 0.037(2) -0.0003(17) 0.0058(18) -0.0043(18)
C14 0.040(2) 0.040(2) 0.036(2) -0.0021(17) 0.0116(18) 0.0023(18)
C15 0.047(2) 0.030(2) 0.0353(19) 0.0013(17) 0.0101(17) 0.0058(18)
C16 0.040(2) 0.032(2) 0.0294(19) -0.0014(15) 0.0056(17) -0.0025(17)
C17 0.070(3) 0.043(2) 0.051(3) 0.009(2) 0.036(2) 0.015(2)
C18 0.061(3) 0.040(2) 0.049(2) 0.005(2) 0.024(2) 0.012(2)

_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 O1 1.952(2) . ?
Co1 N1 2.013(3) . ?
Co1 O3 2.038(2) 2_445 ?
Co1 N2 2.092(3) . ?
Co1 O2 2.164(2) . ?
O1 C1 1.292(4) . ?
O2 C13 1.255(4) . ?
O3 C13 1.262(4) . ?
O3 Co1 2.038(2) 2_455 ?
N1 C11 1.280(4) . ?
N1 C12 1.462(4) . ?
N2 C18 1.335(4) . ?
N2 C14 1.339(4) . ?
C1 C2 1.429(5) . ?
C1 C10 1.427(5) . ?
C2 C3 1.338(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.419(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.407(5) . ?
C4 C9 1.418(5) . ?
C5 C6 1.358(5) . ?
C5 H5A 0.9300 . ?
C6 C7 1.376(6) . ?
C6 H6A 0.9300 . ?
C7 C8 1.378(5) . ?
C7 H7A 0.9300 . ?
C8 C9 1.418(5) . ?
C8 H8A 0.9300 . ?
C9 C10 1.446(5) . ?
C10 C11 1.431(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.502(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C14 C15 1.373(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.384(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.385(5) . ?
C16 C16 1.493(6) 3_585 ?
C17 C18 1.372(5) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Co1 N1 88.84(11) . . ?
O1 Co1 O3 102.70(10) . 2_445 ?
N1 Co1 O3 145.67(11) . 2_445 ?
O1 Co1 N2 97.90(11) . . ?
N1 Co1 N2 120.47(11) . . ?
O3 Co1 N2 90.22(10) 2_445 . ?
O1 Co1 O2 166.92(9) . . ?
N1 Co1 O2 78.23(10) . . ?
O3 Co1 O2 87.23(9) 2_445 . ?
N2 Co1 O2 90.47(10) . . ?
C1 O1 Co1 128.3(2) . . ?
C13 O2 Co1 114.9(2) . . ?
C13 O3 Co1 110.3(2) . 2_455 ?
C11 N1 C12 118.1(3) . . ?
C11 N1 Co1 125.3(2) . . ?
C12 N1 Co1 116.0(2) . . ?
C18 N2 C14 116.1(3) . . ?
C18 N2 Co1 121.1(2) . . ?
C14 N2 Co1 122.4(2) . . ?
O1 C1 C2 118.2(3) . . ?
O1 C1 C10 124.4(3) . . ?
C2 C1 C10 117.4(3) . . ?
C3 C2 C1 122.6(4) . . ?
C3 C2 H2A 118.7 . . ?
C1 C2 H2A 118.7 . . ?
C2 C3 C4 122.0(4) . . ?
C2 C3 H3A 119.0 . . ?
C4 C3 H3A 119.0 . . ?
C5 C4 C9 120.5(4) . . ?
C5 C4 C3 121.2(4) . . ?
C9 C4 C3 118.3(3) . . ?
C6 C5 C4 121.2(4) . . ?
C6 C5 H5A 119.4 . . ?
C4 C5 H5A 119.4 . . ?
C5 C6 C7 119.5(4) . . ?
C5 C6 H6A 120.2 . . ?
C7 C6 H6A 120.2 . . ?
C6 C7 C8 121.0(4) . . ?
C6 C7 H7A 119.5 . . ?
C8 C7 H7A 119.5 . . ?
C7 C8 C9 121.6(4) . . ?
C7 C8 H8A 119.2 . . ?
C9 C8 H8A 119.2 . . ?
C4 C9 C8 116.1(3) . . ?
C4 C9 C10 119.8(3) . . ?
C8 C9 C10 124.1(3) . . ?
C1 C10 C11 120.9(3) . . ?
C1 C10 C9 119.8(3) . . ?
C11 C10 C9 119.3(3) . . ?
N1 C11 C10 127.5(3) . . ?
N1 C11 H11A 116.3 . . ?
C10 C11 H11A 116.3 . . ?
N1 C12 C13 110.3(3) . . ?
N1 C12 H12A 109.6 . . ?
C13 C12 H12A 109.6 . . ?
N1 C12 H12B 109.6 . . ?
C13 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
O2 C13 O3 123.8(3) . . ?
O2 C13 C12 118.7(3) . . ?
O3 C13 C12 117.5(3) . . ?
N2 C14 C15 123.7(3) . . ?
N2 C14 H14A 118.1 . . ?
C15 C14 H14A 118.1 . . ?
C14 C15 C16 120.2(3) . . ?
C14 C15 H15A 119.9 . . ?
C16 C15 H15A 119.9 . . ?
C15 C16 C17 115.9(3) . . ?
C15 C16 C16 121.7(4) . 3_585 ?
C17 C16 C16 122.5(4) . 3_585 ?
C18 C17 C16 120.7(3) . . ?
C18 C17 H17A 119.7 . . ?
C16 C17 H17A 119.7 . . ?
N2 C18 C17 123.4(4) . . ?
N2 C18 H18A 118.3 . . ?
C17 C18 H18A 118.3 . . ?

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 Co1 O1 C1 24.2(3) . . . . ?
O3 Co1 O1 C1 -123.2(3) 2_445 . . . ?
N2 Co1 O1 C1 144.8(3) . . . . ?
O2 Co1 O1 C1 15.5(6) . . . . ?
O1 Co1 O2 C13 13.5(6) . . . . ?
N1 Co1 O2 C13 4.6(2) . . . . ?
O3 Co1 O2 C13 153.3(2) 2_445 . . . ?
N2 Co1 O2 C13 -116.5(2) . . . . ?
O1 Co1 N1 C11 -18.5(3) . . . . ?
O3 Co1 N1 C11 92.6(4) 2_445 . . . ?
N2 Co1 N1 C11 -117.0(3) . . . . ?
O2 Co1 N1 C11 159.5(3) . . . . ?
O1 Co1 N1 C12 170.7(3) . . . . ?
O3 Co1 N1 C12 -78.1(3) 2_445 . . . ?
N2 Co1 N1 C12 72.3(3) . . . . ?
O2 Co1 N1 C12 -11.3(2) . . . . ?
O1 Co1 N2 C18 12.2(3) . . . . ?
N1 Co1 N2 C18 105.5(3) . . . . ?
O3 Co1 N2 C18 -90.7(3) 2_445 . . . ?
O2 Co1 N2 C18 -177.9(3) . . . . ?
O1 Co1 N2 C14 -175.2(3) . . . . ?
N1 Co1 N2 C14 -81.8(3) . . . . ?
O3 Co1 N2 C14 82.0(3) 2_445 . . . ?
O2 Co1 N2 C14 -5.2(3) . . . . ?
Co1 O1 C1 C2 160.3(2) . . . . ?
Co1 O1 C1 C10 -19.9(5) . . . . ?
O1 C1 C2 C3 -178.0(3) . . . . ?
C10 C1 C2 C3 2.3(5) . . . . ?
C1 C2 C3 C4 -1.5(6) . . . . ?
C2 C3 C4 C5 177.8(4) . . . . ?
C2 C3 C4 C9 -1.1(6) . . . . ?
C9 C4 C5 C6 -2.0(7) . . . . ?
C3 C4 C5 C6 179.2(5) . . . . ?
C4 C5 C6 C7 1.3(8) . . . . ?
C5 C6 C7 C8 -0.5(8) . . . . ?
C6 C7 C8 C9 0.4(8) . . . . ?
C5 C4 C9 C8 1.9(6) . . . . ?
C3 C4 C9 C8 -179.3(4) . . . . ?
C5 C4 C9 C10 -176.0(4) . . . . ?
C3 C4 C9 C10 2.9(6) . . . . ?
C7 C8 C9 C4 -1.1(7) . . . . ?
C7 C8 C9 C10 176.7(4) . . . . ?
O1 C1 C10 C11 1.3(6) . . . . ?
C2 C1 C10 C11 -178.9(3) . . . . ?
O1 C1 C10 C9 179.9(3) . . . . ?
C2 C1 C10 C9 -0.4(5) . . . . ?
C4 C9 C10 C1 -2.1(5) . . . . ?
C8 C9 C10 C1 -179.8(4) . . . . ?
C4 C9 C10 C11 176.5(4) . . . . ?
C8 C9 C10 C11 -1.2(6) . . . . ?
C12 N1 C11 C10 179.8(4) . . . . ?
Co1 N1 C11 C10 9.2(6) . . . . ?
C1 C10 C11 N1 3.8(6) . . . . ?
C9 C10 C11 N1 -174.8(4) . . . . ?
C11 N1 C12 C13 -155.8(3) . . . . ?
Co1 N1 C12 C13 15.6(4) . . . . ?
Co1 O2 C13 O3 -177.8(3) . . . . ?
Co1 O2 C13 C12 3.0(4) . . . . ?
Co1 O3 C13 O2 -4.9(4) 2_455 . . . ?
Co1 O3 C13 C12 174.4(3) 2_455 . . . ?
N1 C12 C13 O2 -12.0(5) . . . . ?
N1 C12 C13 O3 168.7(3) . . . . ?
C18 N2 C14 C15 0.9(5) . . . . ?
Co1 N2 C14 C15 -172.2(3) . . . . ?
N2 C14 C15 C16 0.6(6) . . . . ?
C14 C15 C16 C17 -1.8(5) . . . . ?
C14 C15 C16 C16 177.8(4) . . . 3_585 ?
C15 C16 C17 C18 1.5(6) . . . . ?
C16 C16 C17 C18 -178.0(4) 3_585 . . . ?
C14 N2 C18 C17 -1.1(6) . . . . ?
Co1 N2 C18 C17 172.0(3) . . . . ?
C16 C17 C18 N2 -0.1(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.942
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.083