# Electronic Supplementary Material (ESI) for ChemComm.
# 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_p-sr

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H7 Co N2 O4'
_chemical_formula_weight         302.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Co Co -2.3653 3.6143 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbam

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

_cell_length_a                   13.2606(15)
_cell_length_b                   17.5002(17)
_cell_length_c                   7.1051(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1648.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    473(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    8.259
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.4373
_exptl_absorpt_correction_T_max  0.4922
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      473(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4871
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         4.18
_diffrn_reflns_theta_max         67.02
_reflns_number_total             1601
_reflns_number_gt                1269
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] 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         1601
_refine_ls_number_parameters     106
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0768
_refine_ls_wR_factor_ref         0.2708
_refine_ls_wR_factor_gt          0.2564
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.004

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 0.04063(8) -0.11448(5) 0.5000 0.0288(6) Uani 1 2 d S . .
O1 O 0.1568(4) -0.0402(3) 0.5000 0.0433(16) Uani 1 2 d S . .
O2 O 0.1022(4) 0.0783(3) 0.5000 0.0447(16) Uani 1 2 d S . .
O3 O 0.3502(4) 0.2911(3) 0.5000 0.0367(15) Uani 1 2 d S . .
O4 O 0.5120(4) 0.2666(3) 0.5000 0.0339(14) Uani 1 2 d S . .
N1 N 0.0401(3) -0.1133(2) 0.1968(10) 0.0346(14) Uani 1 1 d . . .
C1 C 0.1694(5) 0.0290(4) 0.5000 0.0196(14) Uani 1 2 d S . .
C2 C 0.2785(5) 0.0584(4) 0.5000 0.0219(15) Uani 1 2 d S . .
C3 C 0.2983(5) 0.1367(4) 0.5000 0.0278(16) Uani 1 2 d S . .
H3 H 0.2462 0.1723 0.5000 0.033 Uiso 1 2 calc SR . .
C4 C 0.3986(5) 0.1597(4) 0.5000 0.0276(17) Uani 1 2 d S . .
C5 C 0.4763(6) 0.1063(4) 0.5000 0.0280(19) Uani 1 2 d S . .
H5 H 0.5425 0.1237 0.5000 0.034 Uiso 1 2 calc SR . .
C6 C 0.4589(5) 0.0294(4) 0.5000 0.0271(17) Uani 1 2 d S . .
C7 C 0.3550(5) 0.0049(4) 0.5000 0.0281(17) Uani 1 2 d S . .
H7 H 0.3396 -0.0470 0.5000 0.034 Uiso 1 2 calc SR . .
C8 C 0.4212(6) 0.2439(4) 0.5000 0.038(2) Uani 1 2 d S . .
C9 C -0.0422(4) -0.1255(5) 0.0957(14) 0.056(2) Uani 1 1 d . . .
H9 H -0.1027 -0.1346 0.1583 0.067 Uiso 1 1 calc R . .
C10 C 0.1247(5) -0.1005(4) 0.0966(12) 0.0506(18) Uani 1 1 d . . .
H10 H 0.1848 -0.0914 0.1602 0.061 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 0.0142(7) 0.0067(7) 0.0656(11) 0.000 0.000 0.0000(4)
O1 0.018(3) 0.015(3) 0.097(5) 0.000 0.000 0.003(2)
O2 0.017(2) 0.019(3) 0.098(5) 0.000 0.000 0.002(2)
O3 0.019(2) 0.010(2) 0.081(4) 0.000 0.000 -0.003(2)
O4 0.017(2) 0.013(2) 0.072(4) 0.000 0.000 -0.002(2)
N1 0.025(3) 0.017(3) 0.063(4) 0.001(2) -0.008(2) 0.0004(15)
C1 0.019(3) 0.014(3) 0.026(3) 0.000 0.000 -0.006(3)
C2 0.022(3) 0.014(3) 0.030(4) 0.000 0.000 -0.003(3)
C3 0.021(4) 0.019(3) 0.044(5) 0.000 0.000 -0.002(3)
C4 0.027(4) 0.013(3) 0.043(4) 0.000 0.000 -0.005(3)
C5 0.011(3) 0.015(3) 0.058(5) 0.000 0.000 -0.002(2)
C6 0.021(4) 0.012(3) 0.048(5) 0.000 0.000 0.002(3)
C7 0.021(4) 0.011(3) 0.053(5) 0.000 0.000 -0.007(3)
C8 0.023(4) 0.014(4) 0.078(6) 0.000 0.000 0.000(3)
C9 0.020(3) 0.070(5) 0.077(5) 0.009(4) 0.001(3) -0.011(3)
C10 0.019(3) 0.047(3) 0.085(5) 0.000(3) 0.003(3) -0.005(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 O2 1.997(5) 5_556 ?
Co1 O1 2.016(5) . ?
Co1 N1 2.154(7) . ?
Co1 N1 2.154(7) 6_556 ?
Co1 O4 2.195(5) 7_655 ?
Co1 O3 2.196(5) 7_655 ?
O1 C1 1.221(8) . ?
O2 C1 1.241(8) . ?
O2 Co1 1.997(5) 5_556 ?
O3 C8 1.252(9) . ?
O3 Co1 2.196(5) 7_665 ?
O4 C8 1.268(10) . ?
O4 Co1 2.195(5) 7_665 ?
N1 C9 1.325(9) . ?
N1 C10 1.347(8) . ?
C1 C2 1.536(9) . ?
C2 C7 1.380(9) . ?
C2 C3 1.396(9) . ?
C3 C4 1.389(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(11) . ?
C4 C8 1.505(10) . ?
C5 C6 1.366(11) . ?
C5 H5 0.9300 . ?
C6 C7 1.442(9) . ?
C6 C6 1.499(14) 5_656 ?
C7 H7 0.9300 . ?
C9 C9 1.36(2) 6 ?
C9 H9 0.9300 . ?
C10 C10 1.373(17) 6 ?
C10 H10 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
O2 Co1 O1 121.4(2) 5_556 . ?
O2 Co1 N1 89.64(11) 5_556 . ?
O1 Co1 N1 89.77(11) . . ?
O2 Co1 N1 89.64(11) 5_556 6_556 ?
O1 Co1 N1 89.77(11) . 6_556 ?
N1 Co1 N1 178.8(2) . 6_556 ?
O2 Co1 O4 89.9(2) 5_556 7_655 ?
O1 Co1 O4 148.7(2) . 7_655 ?
N1 Co1 O4 90.48(11) . 7_655 ?
N1 Co1 O4 90.48(11) 6_556 7_655 ?
O2 Co1 O3 149.7(2) 5_556 7_655 ?
O1 Co1 O3 88.9(2) . 7_655 ?
N1 Co1 O3 90.55(11) . 7_655 ?
N1 Co1 O3 90.55(11) 6_556 7_655 ?
O4 Co1 O3 59.77(18) 7_655 7_655 ?
C1 O1 Co1 138.0(5) . . ?
C1 O2 Co1 154.3(5) . 5_556 ?
C8 O3 Co1 90.1(4) . 7_665 ?
C8 O4 Co1 89.7(4) . 7_665 ?
C9 N1 C10 115.3(7) . . ?
C9 N1 Co1 122.9(5) . . ?
C10 N1 Co1 121.8(5) . . ?
O1 C1 O2 126.3(7) . . ?
O1 C1 C2 117.4(6) . . ?
O2 C1 C2 116.3(6) . . ?
C7 C2 C3 121.8(6) . . ?
C7 C2 C1 117.7(6) . . ?
C3 C2 C1 120.4(6) . . ?
C2 C3 C4 117.7(7) . . ?
C2 C3 H3 121.2 . . ?
C4 C3 H3 121.2 . . ?
C5 C4 C3 121.0(7) . . ?
C5 C4 C8 120.7(7) . . ?
C3 C4 C8 118.3(7) . . ?
C6 C5 C4 122.5(7) . . ?
C6 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
C5 C6 C7 117.0(7) . . ?
C5 C6 C6 123.6(8) . 5_656 ?
C7 C6 C6 119.4(8) . 5_656 ?
C2 C7 C6 120.0(6) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
O4 C8 O3 120.5(7) . . ?
O4 C8 C4 119.7(7) . . ?
O3 C8 C4 119.8(7) . . ?
N1 C9 C9 122.8(5) . 6 ?
N1 C9 H9 118.6 . . ?
C9 C9 H9 118.6 6 . ?
N1 C10 C10 121.9(4) . 6 ?
N1 C10 H10 119.0 . . ?
C10 C10 H10 119.0 6 . ?

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
O2 Co1 O1 C1 0.0 5_556 . . . ?
N1 Co1 O1 C1 89.45(11) . . . . ?
N1 Co1 O1 C1 -89.45(11) 6_556 . . . ?
O4 Co1 O1 C1 180.0 7_655 . . . ?
O3 Co1 O1 C1 180.0 7_655 . . . ?
O2 Co1 N1 C9 -30.0(5) 5_556 . . . ?
O1 Co1 N1 C9 -151.4(5) . . . . ?
N1 Co1 N1 C9 -84(11) 6_556 . . . ?
O4 Co1 N1 C9 59.9(5) 7_655 . . . ?
O3 Co1 N1 C9 119.7(5) 7_655 . . . ?
O2 Co1 N1 C10 150.6(4) 5_556 . . . ?
O1 Co1 N1 C10 29.2(4) . . . . ?
N1 Co1 N1 C10 97(11) 6_556 . . . ?
O4 Co1 N1 C10 -119.5(4) 7_655 . . . ?
O3 Co1 N1 C10 -59.7(4) 7_655 . . . ?
Co1 O1 C1 O2 0.0 . . . . ?
Co1 O1 C1 C2 180.0 . . . . ?
Co1 O2 C1 O1 0.0 5_556 . . . ?
Co1 O2 C1 C2 180.0 5_556 . . . ?
O1 C1 C2 C7 0.0 . . . . ?
O2 C1 C2 C7 180.0 . . . . ?
O1 C1 C2 C3 180.0 . . . . ?
O2 C1 C2 C3 0.0 . . . . ?
C7 C2 C3 C4 0.0 . . . . ?
C1 C2 C3 C4 180.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C2 C3 C4 C8 180.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C8 C4 C5 C6 180.0 . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C4 C5 C6 C6 180.0 . . . 5_656 ?
C3 C2 C7 C6 0.0 . . . . ?
C1 C2 C7 C6 180.0 . . . . ?
C5 C6 C7 C2 0.0 . . . . ?
C6 C6 C7 C2 180.0 5_656 . . . ?
Co1 O4 C8 O3 0.0 7_665 . . . ?
Co1 O4 C8 C4 180.0 7_665 . . . ?
Co1 O3 C8 O4 0.0 7_665 . . . ?
Co1 O3 C8 C4 180.0 7_665 . . . ?
C5 C4 C8 O4 0.0 . . . . ?
C3 C4 C8 O4 180.0 . . . . ?
C5 C4 C8 O3 180.0 . . . . ?
C3 C4 C8 O3 0.0 . . . . ?
C10 N1 C9 C9 0.1(6) . . . 6 ?
Co1 N1 C9 C9 -179.29(13) . . . 6 ?
C9 N1 C10 C10 -0.1(6) . . . 6 ?
Co1 N1 C10 C10 179.30(13) . . . 6 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        67.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.852
_refine_diff_density_rms         0.107
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.006 0.374 0.000 655 257 ' '
_platon_squeeze_details          
;
;
_database_code_depnum_ccdc_archive 'CCDC 981845'
#######################################################################
#
#                 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_p

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H11 Co N2 O4'
_chemical_formula_weight         378.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Co Co -2.3653 3.6143 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   p21/c

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

_cell_length_a                   11.3988(2)
_cell_length_b                   17.3695(2)
_cell_length_c                   13.24337(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.4376(15)
_cell_angle_gamma                90.00
_cell_volume                     2619.71(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    473(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.959
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    5.281
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.5698
_exptl_absorpt_correction_T_max  0.6202
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      473(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18500
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.88
_diffrn_reflns_theta_max         67.07
_reflns_number_total             4680
_reflns_number_gt                4086
_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)+(0.1079P)²+8.0903P] 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         4680
_refine_ls_number_parameters     226
_refine_ls_number_restraints     342
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0725
_refine_ls_wR_factor_ref         0.2087
_refine_ls_wR_factor_gt          0.2031
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.052
_refine_ls_shift/su_mean         0.004

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 0.52981(5) 0.61206(3) 0.46144(4) 0.0148(2) Uani 1 1 d . . .
O1 O 0.4590(3) 0.42334(17) 0.3945(2) 0.0253(7) Uani 1 1 d . . .
O2 O 0.5266(3) 0.53733(16) 0.3452(2) 0.0240(6) Uani 1 1 d . . .
O3 O 0.4724(3) 0.23306(17) -0.0142(2) 0.0304(7) Uani 1 1 d . . .
O4 O 0.4723(3) 0.20646(16) 0.1465(2) 0.0284(7) Uani 1 1 d . . .
N1 N 0.7180(3) 0.60959(19) 0.4629(3) 0.0239(8) Uani 1 1 d . . .
N2 N 1.3414(3) 0.6109(2) 0.4612(3) 0.0240(8) Uani 1 1 d . . .
C1 C 0.4920(4) 0.4697(2) 0.3288(3) 0.0198(7) Uani 1 1 d U . .
C2 C 0.4885(4) 0.4427(2) 0.2214(3) 0.0214(7) Uani 1 1 d U . .
C3 C 0.4772(4) 0.3645(2) 0.2004(3) 0.0231(7) Uani 1 1 d U . .
H3 H 0.4689 0.3292 0.2523 0.028 Uiso 1 1 calc R . .
C4 C 0.4785(4) 0.3401(2) 0.1006(3) 0.0241(7) Uani 1 1 d U . .
C5 C 0.4739(4) 0.2554(2) 0.0765(3) 0.0237(8) Uani 1 1 d U . .
C6 C 0.4867(4) 0.3928(2) 0.0233(3) 0.0260(8) Uani 1 1 d U . .
H6 H 0.4862 0.3752 -0.0431 0.031 Uiso 1 1 calc R . .
C7 C 0.4957(4) 0.4719(2) 0.0418(3) 0.0236(7) Uani 1 1 d U . .
C8 C 0.4978(4) 0.4957(2) 0.1434(3) 0.0226(7) Uani 1 1 d U . .
H8 H 0.5055 0.5477 0.1587 0.027 Uiso 1 1 calc R . .
C9 C 0.7845(5) 0.6249(5) 0.5417(5) 0.0655(12) Uani 1 1 d U . .
H9 H 0.7476 0.6361 0.6012 0.079 Uiso 1 1 calc R . .
C10 C 0.9052(5) 0.6261(5) 0.5449(5) 0.0647(11) Uani 1 1 d U . .
H10 H 0.9461 0.6392 0.6047 0.078 Uiso 1 1 calc R . .
C11 C 0.9650(5) 0.6083(4) 0.4621(4) 0.0535(10) Uani 1 1 d U . .
C12 C 1.0947(5) 0.6090(4) 0.4608(4) 0.0531(10) Uani 1 1 d U . .
C13 C 1.1637(5) 0.6237(4) 0.5473(4) 0.0578(10) Uani 1 1 d U . .
H13 H 1.1284 0.6323 0.6084 0.069 Uiso 1 1 calc R . .
C14 C 1.2838(5) 0.6259(4) 0.5436(4) 0.0543(11) Uani 1 1 d U . .
H14 H 1.3272 0.6385 0.6024 0.065 Uiso 1 1 calc R . .
C15 C 1.2753(5) 0.5961(4) 0.3780(4) 0.0497(10) Uani 1 1 d U . .
H15 H 1.3129 0.5867 0.3183 0.060 Uiso 1 1 calc R . .
C16 C 1.1537(5) 0.5940(4) 0.3754(4) 0.0536(10) Uani 1 1 d U . .
H16 H 1.1122 0.5823 0.3153 0.064 Uiso 1 1 calc R . .
C17 C 0.8954(5) 0.5929(5) 0.3808(5) 0.0669(11) Uani 1 1 d U . .
H17 H 0.9298 0.5832 0.3196 0.080 Uiso 1 1 calc R . .
C18 C 0.7759(5) 0.5908(5) 0.3840(5) 0.0678(12) Uani 1 1 d U . .
H18 H 0.7333 0.5750 0.3262 0.081 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 0.0236(4) 0.0111(3) 0.0096(3) -0.0004(2) 0.0005(2) -0.0002(2)
O1 0.0368(17) 0.0270(16) 0.0122(13) 0.0033(12) 0.0007(12) -0.0013(13)
O2 0.0384(17) 0.0187(14) 0.0147(13) -0.0047(11) 0.0006(12) -0.0034(12)
O3 0.059(2) 0.0154(15) 0.0170(15) -0.0029(11) 0.0025(14) -0.0031(14)
O4 0.056(2) 0.0118(14) 0.0172(14) 0.0021(11) -0.0002(13) -0.0006(13)
N1 0.030(2) 0.0213(18) 0.0209(18) 0.0004(13) 0.0002(15) -0.0003(14)
N2 0.0290(19) 0.0227(19) 0.0203(18) -0.0032(13) 0.0015(15) 0.0000(14)
C1 0.0284(17) 0.0161(16) 0.0148(16) 0.0007(13) 0.0009(13) 0.0008(13)
C2 0.0336(16) 0.0163(14) 0.0142(14) -0.0011(12) -0.0001(13) -0.0009(13)
C3 0.0371(16) 0.0168(15) 0.0154(14) 0.0020(13) 0.0013(13) -0.0008(13)
C4 0.0396(16) 0.0159(15) 0.0165(14) -0.0019(13) -0.0007(13) -0.0018(13)
C5 0.0369(18) 0.0170(16) 0.0171(15) -0.0008(13) 0.0000(14) -0.0018(14)
C6 0.0434(17) 0.0194(16) 0.0153(15) -0.0018(13) 0.0000(14) -0.0010(14)
C7 0.0392(17) 0.0167(16) 0.0150(15) -0.0024(13) 0.0006(13) -0.0013(13)
C8 0.0366(16) 0.0152(15) 0.0159(15) -0.0014(13) 0.0002(13) -0.0010(13)
C9 0.035(2) 0.127(3) 0.035(2) -0.030(2) 0.0035(17) -0.001(2)
C10 0.0348(18) 0.123(3) 0.0359(18) -0.0255(19) -0.0005(16) -0.0013(19)
C11 0.0278(17) 0.106(2) 0.0268(17) -0.0161(16) 0.0017(14) 0.0010(16)
C12 0.0276(17) 0.105(2) 0.0261(16) -0.0163(16) 0.0001(14) 0.0014(16)
C13 0.0322(18) 0.112(3) 0.0289(18) -0.0203(18) 0.0012(15) 0.0033(18)
C14 0.0287(19) 0.107(3) 0.0274(19) -0.0203(19) -0.0009(16) 0.0039(19)
C15 0.0273(18) 0.099(3) 0.0229(18) -0.0154(19) -0.0004(15) 0.0034(19)
C16 0.0278(17) 0.107(2) 0.0265(17) -0.0184(18) -0.0002(15) 0.0037(18)
C17 0.0368(18) 0.129(3) 0.0349(18) -0.0214(19) 0.0030(16) -0.0001(19)
C18 0.035(2) 0.133(3) 0.035(2) -0.021(2) 0.0010(17) -0.002(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 2.003(3) 3_666 ?
Co1 O2 2.012(3) . ?
Co1 N1 2.145(4) . ?
Co1 N2 2.147(4) 1_455 ?
Co1 O4 2.175(3) 2_655 ?
Co1 O3 2.215(3) 2_655 ?
O1 C1 1.255(5) . ?
O1 Co1 2.003(3) 3_666 ?
O2 C1 1.255(5) . ?
O3 C5 1.262(5) . ?
O3 Co1 2.215(3) 2_645 ?
O4 C5 1.259(5) . ?
O4 Co1 2.175(3) 2_645 ?
N1 C9 1.290(7) . ?
N1 C18 1.301(7) . ?
N2 C14 1.324(6) . ?
N2 C15 1.333(6) . ?
N2 Co1 2.147(4) 1_655 ?
C1 C2 1.497(5) . ?
C2 C3 1.390(6) . ?
C2 C8 1.391(6) . ?
C3 C4 1.388(6) . ?
C3 H3 0.9300 . ?
C4 C6 1.379(6) . ?
C4 C5 1.505(6) . ?
C6 C7 1.399(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.407(5) . ?
C7 C7 1.484(8) 3_665 ?
C8 H8 0.9300 . ?
C9 C10 1.375(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.352(8) . ?
C10 H10 0.9300 . ?
C11 C17 1.337(8) . ?
C11 C12 1.479(8) . ?
C12 C16 1.366(7) . ?
C12 C13 1.386(8) . ?
C13 C14 1.373(8) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.385(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.365(9) . ?
C17 H17 0.9300 . ?
C18 H18 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 O2 121.91(12) 3_666 . ?
O1 Co1 N1 87.84(13) 3_666 . ?
O2 Co1 N1 88.83(13) . . ?
O1 Co1 N2 91.24(13) 3_666 1_455 ?
O2 Co1 N2 90.42(13) . 1_455 ?
N1 Co1 N2 178.27(14) . 1_455 ?
O1 Co1 O4 148.85(12) 3_666 2_655 ?
O2 Co1 O4 89.11(11) . 2_655 ?
N1 Co1 O4 90.24(13) . 2_655 ?
N2 Co1 O4 91.30(13) 1_455 2_655 ?
O1 Co1 O3 89.53(12) 3_666 2_655 ?
O2 Co1 O3 148.56(11) . 2_655 ?
N1 Co1 O3 92.33(13) . 2_655 ?
N2 Co1 O3 89.12(13) 1_455 2_655 ?
O4 Co1 O3 59.48(10) 2_655 2_655 ?
C1 O1 Co1 148.0(3) . 3_666 ?
C1 O2 Co1 137.0(3) . . ?
C5 O3 Co1 89.5(2) . 2_645 ?
C5 O4 Co1 91.5(2) . 2_645 ?
C9 N1 C18 113.6(5) . . ?
C9 N1 Co1 123.8(4) . . ?
C18 N1 Co1 122.6(4) . . ?
C14 N2 C15 115.9(4) . . ?
C14 N2 Co1 121.9(3) . 1_655 ?
C15 N2 Co1 122.3(3) . 1_655 ?
O1 C1 O2 125.6(4) . . ?
O1 C1 C2 117.4(3) . . ?
O2 C1 C2 117.0(3) . . ?
C3 C2 C8 120.4(4) . . ?
C3 C2 C1 119.7(4) . . ?
C8 C2 C1 119.9(4) . . ?
C4 C3 C2 119.0(4) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C6 C4 C3 120.5(4) . . ?
C6 C4 C5 119.6(4) . . ?
C3 C4 C5 119.9(4) . . ?
O4 C5 O3 119.5(4) . . ?
O4 C5 C4 120.4(4) . . ?
O3 C5 C4 120.1(4) . . ?
C4 C6 C7 121.9(4) . . ?
C4 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C6 C7 C8 117.0(4) . . ?
C6 C7 C7 121.5(4) . 3_665 ?
C8 C7 C7 121.4(5) . 3_665 ?
C2 C8 C7 121.1(4) . . ?
C2 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
N1 C9 C10 125.5(5) . . ?
N1 C9 H9 117.3 . . ?
C10 C9 H9 117.3 . . ?
C11 C10 C9 120.7(6) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C17 C11 C10 113.4(6) . . ?
C17 C11 C12 123.5(5) . . ?
C10 C11 C12 123.1(5) . . ?
C16 C12 C13 115.9(5) . . ?
C16 C12 C11 122.4(5) . . ?
C13 C12 C11 121.7(5) . . ?
C14 C13 C12 120.5(5) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
N2 C14 C13 123.7(5) . . ?
N2 C14 H14 118.2 . . ?
C13 C14 H14 118.2 . . ?
N2 C15 C16 123.8(5) . . ?
N2 C15 H15 118.1 . . ?
C16 C15 H15 118.1 . . ?
C12 C16 C15 120.1(5) . . ?
C12 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C11 C17 C18 122.6(6) . . ?
C11 C17 H17 118.7 . . ?
C18 C17 H17 118.7 . . ?
N1 C18 C17 124.0(6) . . ?
N1 C18 H18 118.0 . . ?
C17 C18 H18 118.0 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        67.07
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.659
_refine_diff_density_min         -1.202
_refine_diff_density_rms         0.100
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.351 -0.011 1373 379 ' '
_platon_squeeze_details          
;
;
_database_code_depnum_ccdc_archive 'CCDC 981846'
