# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2013


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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  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. 
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#  fide research purposes only. It may contain copyright material 
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data_100315d_0m
_database_code_depnum_ccdc_archive 'CCDC 833060'
#TrackingRef '15799_web_deposit_cif_file_0_Hao-LingSun_1354233741.revised.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H12 Co O6.50'
_chemical_formula_weight         355.18

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'
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           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                   8.3499(2)
_cell_length_b                   12.4558(3)
_cell_length_c                   13.7987(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1435.13(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2021
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      27.62

_exptl_crystal_description       neddle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             724
_exptl_absorpt_coefficient_mu    1.227
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7098
_exptl_absorpt_correction_T_max  0.9300
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4651
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         27.62
_reflns_number_total             1737
_reflns_number_gt                1491
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0539P)^2^+1.1878P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1737
_refine_ls_number_parameters     127
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.1061
_refine_ls_wR_factor_gt          0.1022
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3335(3) 0.79928(18) 0.85631(15) 0.0242(5) Uani 1 1 d . . .
C2 C 0.2602(3) 0.84060(19) 0.76410(16) 0.0254(5) Uani 1 1 d . . .
C3 C 0.2935(4) 0.9435(2) 0.7316(2) 0.0444(7) Uani 1 1 d . . .
H3 H 0.3611 0.9877 0.7673 0.053 Uiso 1 1 calc R . .
C4 C 0.2264(4) 0.9805(2) 0.6463(2) 0.0457(8) Uani 1 1 d . . .
H4 H 0.2505 1.0495 0.6250 0.055 Uiso 1 1 calc R . .
C5 C 0.1246(3) 0.91754(19) 0.59227(16) 0.0250(5) Uani 1 1 d . . .
C6 C 0.0550(4) 0.9607(3) 0.5000 0.0239(6) Uani 1 2 d S . .
C7 C 0.0896(3) 0.8152(2) 0.62567(19) 0.0346(6) Uani 1 1 d . . .
H7 H 0.0205 0.7716 0.5904 0.042 Uiso 1 1 calc R . .
C8 C 0.1564(3) 0.7771(2) 0.71091(17) 0.0320(5) Uani 1 1 d . . .
H8 H 0.1312 0.7085 0.7326 0.038 Uiso 1 1 calc R . .
Co1 Co 0.10972(5) 0.68883(3) 1.0000 0.02263(16) Uani 1 2 d S . .
O1 O 0.2810(2) 0.71208(14) 0.89049(12) 0.0330(4) Uani 1 1 d . A .
O2 O 0.4454(2) 0.85373(14) 0.89270(12) 0.0298(4) Uani 1 1 d . . .
O4 O 0.1882(3) 0.52873(19) 1.0000 0.0340(6) Uani 1 2 d SD A .
H4C H 0.193(12) 0.472(5) 0.955(5) 0.13(2) Uiso 0.50 1 d PD . .
O5 O 0.0000 1.0000 1.1338(7) 0.107(4) Uani 0.50 2 d SP . .
O3 O 0.053(2) 0.8537(13) 1.0000 0.029(3) Uani 0.50 2 d SPDU A 1
H3C H 0.074(6) 0.921(2) 1.031(3) 0.13(2) Uiso 1 1 d D B 1
O3' O 0.055(2) 0.8554(14) 1.0287(14) 0.029(3) Uani 0.25 1 d PU . 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 0.0238(10) 0.0292(11) 0.0197(10) 0.0002(9) 0.0004(9) 0.0030(9)
C2 0.0245(11) 0.0292(11) 0.0224(10) 0.0026(9) -0.0024(9) 0.0022(9)
C3 0.0518(17) 0.0354(14) 0.0462(16) 0.0107(12) -0.0270(14) -0.0142(13)
C4 0.0555(18) 0.0322(14) 0.0494(16) 0.0164(13) -0.0239(15) -0.0123(13)
C5 0.0260(11) 0.0301(11) 0.0190(10) 0.0009(9) -0.0005(8) 0.0060(9)
C6 0.0274(16) 0.0274(16) 0.0171(13) 0.000 0.000 0.0019(13)
C7 0.0468(16) 0.0336(13) 0.0235(11) 0.0001(10) -0.0099(11) -0.0080(12)
C8 0.0433(14) 0.0279(12) 0.0249(11) 0.0057(9) -0.0051(11) -0.0054(11)
Co1 0.0238(3) 0.0217(2) 0.0224(2) 0.000 0.000 -0.00247(17)
O1 0.0373(10) 0.0377(10) 0.0240(8) 0.0068(7) -0.0009(7) -0.0068(8)
O2 0.0308(9) 0.0301(9) 0.0286(8) 0.0026(7) -0.0101(7) -0.0007(7)
O4 0.0354(14) 0.0250(12) 0.0417(14) 0.000 0.000 0.0020(11)
O5 0.122(8) 0.119(8) 0.079(6) 0.000 0.000 0.061(7)
O3 0.029(4) 0.025(3) 0.031(10) 0.000 0.000 -0.003(3)
O3' 0.032(4) 0.027(4) 0.028(7) 0.001(4) -0.003(4) -0.003(3)

_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 O2 1.259(3) . ?
C1 O1 1.263(3) . ?
C1 C2 1.503(3) . ?
C2 C8 1.384(3) . ?
C2 C3 1.386(4) . ?
C3 C4 1.383(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(4) . ?
C4 H4 0.9300 . ?
C5 C7 1.387(3) . ?
C5 C6 1.500(3) . ?
C6 C6 1.342(7) 5_576 ?
C6 C5 1.500(3) 6_556 ?
C7 C8 1.385(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
Co1 O2 2.0869(16) 7_575 ?
Co1 O2 2.0869(16) 4_467 ?
Co1 O4 2.099(2) . ?
Co1 O1 2.1006(18) 6_557 ?
Co1 O1 2.1006(18) . ?
Co1 O3 2.108(17) . ?
Co1 O3' 2.161(17) 6_557 ?
Co1 O3' 2.161(17) . ?
O2 Co1 2.0869(16) 7_675 ?
O4 H4C 0.94(2) . ?
O3 H3C 0.965(19) . ?
O3' O3' 0.79(4) 6_557 ?
O3' H3C 0.84(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 124.9(2) . . ?
O2 C1 C2 117.1(2) . . ?
O1 C1 C2 118.0(2) . . ?
C8 C2 C3 118.8(2) . . ?
C8 C2 C1 120.6(2) . . ?
C3 C2 C1 120.6(2) . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 121.4(2) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C7 118.3(2) . . ?
C4 C5 C6 119.6(2) . . ?
C7 C5 C6 122.0(2) . . ?
C6 C6 C5 121.80(13) 5_576 . ?
C6 C6 C5 121.80(13) 5_576 6_556 ?
C5 C6 C5 116.2(3) . 6_556 ?
C8 C7 C5 120.8(2) . . ?
C8 C7 H7 119.6 . . ?
C5 C7 H7 119.6 . . ?
C2 C8 C7 120.5(2) . . ?
C2 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
O2 Co1 O2 90.39(10) 7_575 4_467 ?
O2 Co1 O4 87.93(7) 7_575 . ?
O2 Co1 O4 87.93(7) 4_467 . ?
O2 Co1 O1 173.18(7) 7_575 6_557 ?
O2 Co1 O1 88.41(7) 4_467 6_557 ?
O4 Co1 O1 85.31(8) . 6_557 ?
O2 Co1 O1 88.41(7) 7_575 . ?
O2 Co1 O1 173.18(7) 4_467 . ?
O4 Co1 O1 85.31(7) . . ?
O1 Co1 O1 92.00(10) 6_557 . ?
O2 Co1 O3 95.7(3) 7_575 . ?
O2 Co1 O3 95.7(3) 4_467 . ?
O4 Co1 O3 174.9(5) . . ?
O1 Co1 O3 91.1(3) 6_557 . ?
O1 Co1 O3 91.1(3) . . ?
O2 Co1 O3' 88.5(5) 7_575 6_557 ?
O2 Co1 O3' 103.6(5) 4_467 6_557 ?
O4 Co1 O3' 168.0(5) . 6_557 ?
O1 Co1 O3' 98.3(5) 6_557 6_557 ?
O1 Co1 O3' 83.1(5) . 6_557 ?
O3 Co1 O3' 10.6(5) . 6_557 ?
O2 Co1 O3' 103.6(5) 7_575 . ?
O2 Co1 O3' 88.5(5) 4_467 . ?
O4 Co1 O3' 168.0(5) . . ?
O1 Co1 O3' 83.1(5) 6_557 . ?
O1 Co1 O3' 98.3(5) . . ?
O3 Co1 O3' 10.6(5) . . ?
O3' Co1 O3' 21.2(10) 6_557 . ?
C1 O1 Co1 128.58(16) . . ?
C1 O2 Co1 129.34(15) . 7_675 ?
Co1 O4 H4C 136(6) . . ?
Co1 O3 H3C 144(3) . . ?
O3' O3' Co1 79.4(5) 6_557 . ?
O3' O3' H3C 93(4) 6_557 . ?
Co1 O3' H3C 155(4) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.62
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.085