# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20111129b_0m-sr-sr
_database_code_depnum_ccdc_archive 'CCDC 1020952'
_audit_update_record             
;
2014-08-24 deposited with the CCDC.
2015-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H6 Co N2 O4'
_chemical_formula_sum            'C12 H6 Co N2 O4'
_chemical_formula_weight         301.12

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           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   10.8161(13)
_cell_length_b                   12.6809(15)
_cell_length_c                   13.4170(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.147(2)
_cell_angle_gamma                90.00
_cell_volume                     1716.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5467
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      28.27

_exptl_crystal_description       block
_exptl_crystal_colour            violet
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             604
_exptl_absorpt_coefficient_mu    1.007
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.824
_exptl_absorpt_correction_T_max  0.886
_exptl_absorpt_process_details   'SADABA, (Bruker, 2000)'

_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            9234
_diffrn_reflns_av_R_equivalents  0.1117
_diffrn_reflns_av_sigmaI/netI    0.0680
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3018
_reflns_number_gt                2637
_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)+(0.0537P)²+0.6829P] where P=(Fo²+2Fc²)/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         3012
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1096
_refine_ls_wR_factor_gt          0.1075
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 -0.009 -0.003 -0.005 751 217 ' '
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 0.1361(2) 0.6259(2) 0.92923(19) 0.0274(5) Uani 1 1 d . . .
C2 C 0.2116(2) 0.7037(2) 0.88813(19) 0.0263(5) Uani 1 1 d . . .
C3 C 0.1433(2) 0.7781(2) 0.81261(19) 0.0280(5) Uani 1 1 d . . .
H3 H 0.0511 0.7778 0.7854 0.034 Uiso 1 1 calc R . .
C4 C 0.2117(2) 0.8528(2) 0.77752(19) 0.0273(5) Uani 1 1 d . . .
C5 C 0.1391(3) 0.9251(2) 0.6869(2) 0.0302(6) Uani 1 1 d . . .
C6 C 0.3502(2) 0.8563(2) 0.8212(2) 0.0307(6) Uani 1 1 d . . .
H6 H 0.3959 0.9095 0.8014 0.037 Uiso 1 1 calc R . .
C7 C 0.4195(2) 0.7795(2) 0.8948(2) 0.0283(5) Uani 1 1 d . . .
C8 C 0.3498(2) 0.7029(2) 0.9267(2) 0.0300(6) Uani 1 1 d . . .
H8 H 0.3958 0.6506 0.9743 0.036 Uiso 1 1 calc R . .
C9 C 0.5670(2) 0.7810(2) 0.9373(2) 0.0296(6) Uani 1 1 d . . .
C10 C 0.6375(3) 0.8717(2) 0.9804(3) 0.0491(8) Uani 1 1 d . . .
H10 H 0.5903 0.9326 0.9819 0.059 Uiso 1 1 calc R . .
C11 C 0.8318(3) 0.7871(2) 1.0145(3) 0.0409(7) Uani 1 1 d . . .
H11 H 0.9240 0.7884 1.0420 0.049 Uiso 1 1 calc R . .
C12 C 0.6419(2) 0.6941(2) 0.93495(19) 0.0280(5) Uani 1 1 d . . .
H12 H 0.5990 0.6316 0.9057 0.034 Uiso 1 1 calc R . .
Co1 Co -0.10608(3) 0.57001(2) 0.97097(2) 0.02323(14) Uani 1 1 d . . .
N1 N 0.7753(2) 0.69646(16) 0.97360(16) 0.0267(4) Uani 1 1 d . . .
N2 N 0.7702(3) 0.8760(2) 1.0200(3) 0.0585(8) Uani 1 1 d . . .
O1 O 0.02108(18) 0.65268(15) 0.92128(15) 0.0350(4) Uani 1 1 d . . .
O2 O 0.19307(18) 0.54109(15) 0.96745(15) 0.0351(4) Uani 1 1 d . . .
O3 O 0.02500(19) 0.89737(18) 0.62754(14) 0.0393(5) Uani 1 1 d . . .
O4 O 0.19807(19) 1.00621(16) 0.67368(15) 0.0404(5) Uani 1 1 d . . .

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 0.0236(12) 0.0345(14) 0.0257(12) 0.0001(10) 0.0108(10) -0.0037(11)
C2 0.0219(12) 0.0310(13) 0.0302(12) 0.0020(10) 0.0142(10) -0.0012(10)
C3 0.0189(11) 0.0369(14) 0.0288(12) 0.0030(10) 0.0093(9) 0.0032(10)
C4 0.0224(12) 0.0343(14) 0.0273(12) 0.0056(10) 0.0117(10) 0.0050(10)
C5 0.0297(14) 0.0386(16) 0.0272(12) 0.0065(11) 0.0160(11) 0.0076(11)
C6 0.0230(12) 0.0352(14) 0.0375(14) 0.0091(11) 0.0155(11) 0.0025(11)
C7 0.0205(12) 0.0321(14) 0.0338(13) 0.0061(10) 0.0117(10) 0.0048(10)
C8 0.0217(12) 0.0339(14) 0.0342(13) 0.0097(11) 0.0099(10) 0.0063(10)
C9 0.0221(12) 0.0331(14) 0.0350(13) 0.0081(11) 0.0122(10) 0.0041(10)
C10 0.0291(15) 0.0318(16) 0.088(2) -0.0049(15) 0.0229(15) 0.0040(12)
C11 0.0221(13) 0.0329(15) 0.0648(18) -0.0038(13) 0.0124(13) -0.0003(11)
C12 0.0210(12) 0.0326(14) 0.0306(12) 0.0035(10) 0.0097(10) 0.0012(10)
Co1 0.0166(2) 0.0251(2) 0.0298(2) -0.00061(13) 0.01048(14) 0.00083(12)
N1 0.0196(10) 0.0286(11) 0.0322(11) 0.0012(9) 0.0097(8) 0.0017(8)
N2 0.0262(13) 0.0373(15) 0.107(2) -0.0151(15) 0.0180(14) -0.0022(11)
O1 0.0263(9) 0.0388(11) 0.0475(11) 0.0068(8) 0.0225(8) 0.0006(8)
O2 0.0286(10) 0.0333(10) 0.0449(10) 0.0109(8) 0.0151(8) -0.0002(8)
O3 0.0300(10) 0.0545(12) 0.0282(9) 0.0076(9) 0.0044(8) 0.0065(9)
O4 0.0366(11) 0.0435(12) 0.0408(10) 0.0187(9) 0.0138(9) 0.0048(9)

_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 1.253(3) . ?
C1 O1 1.256(3) . ?
C1 C2 1.507(3) . ?
C2 C3 1.387(4) . ?
C2 C8 1.394(3) . ?
C3 C4 1.385(4) . ?
C3 H3 0.9300 . ?
C4 C6 1.398(3) . ?
C4 C5 1.499(3) . ?
C5 O3 1.254(3) . ?
C5 O4 1.256(3) . ?
C6 C7 1.397(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.388(4) . ?
C7 C9 1.488(3) . ?
C8 H8 0.9300 . ?
C9 C12 1.376(4) . ?
C9 C10 1.385(4) . ?
C10 N2 1.340(4) . ?
C10 H10 0.9300 . ?
C11 N1 1.324(4) . ?
C11 N2 1.326(4) . ?
C11 H11 0.9300 . ?
C12 N1 1.346(3) . ?
C12 H12 0.9300 . ?
Co1 O4 2.0045(18) 2_546 ?
Co1 O1 2.0240(18) . ?
Co1 O2 2.0282(19) 3_567 ?
Co1 N1 2.062(2) 1_455 ?
Co1 O3 2.1084(18) 4_576 ?
Co1 Co1 2.7813(6) 3_567 ?
N1 Co1 2.062(2) 1_655 ?
O2 Co1 2.0282(19) 3_567 ?
O3 Co1 2.1084(18) 4_575 ?
O4 Co1 2.0045(18) 2_556 ?

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 126.4(2) . . ?
O2 C1 C2 117.4(2) . . ?
O1 C1 C2 116.3(2) . . ?
C3 C2 C8 119.6(2) . . ?
C3 C2 C1 119.8(2) . . ?
C8 C2 C1 120.6(2) . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C6 120.1(2) . . ?
C3 C4 C5 120.4(2) . . ?
C6 C4 C5 119.3(2) . . ?
O3 C5 O4 125.0(2) . . ?
O3 C5 C4 116.8(2) . . ?
O4 C5 C4 118.1(2) . . ?
C7 C6 C4 119.7(2) . . ?
C7 C6 H6 120.2 . . ?
C4 C6 H6 120.2 . . ?
C8 C7 C6 119.5(2) . . ?
C8 C7 C9 121.2(2) . . ?
C6 C7 C9 119.3(2) . . ?
C7 C8 C2 120.6(2) . . ?
C7 C8 H8 119.7 . . ?
C2 C8 H8 119.7 . . ?
C12 C9 C10 115.8(2) . . ?
C12 C9 C7 122.7(2) . . ?
C10 C9 C7 121.6(2) . . ?
N2 C10 C9 123.3(3) . . ?
N2 C10 H10 118.3 . . ?
C9 C10 H10 118.3 . . ?
N1 C11 N2 126.5(3) . . ?
N1 C11 H11 116.8 . . ?
N2 C11 H11 116.8 . . ?
N1 C12 C9 122.1(2) . . ?
N1 C12 H12 119.0 . . ?
C9 C12 H12 119.0 . . ?
O4 Co1 O1 92.81(8) 2_546 . ?
O4 Co1 O2 88.44(9) 2_546 3_567 ?
O1 Co1 O2 164.62(8) . 3_567 ?
O4 Co1 N1 103.64(8) 2_546 1_455 ?
O1 Co1 N1 95.97(8) . 1_455 ?
O2 Co1 N1 98.63(8) 3_567 1_455 ?
O4 Co1 O3 164.66(9) 2_546 4_576 ?
O1 Co1 O3 86.21(8) . 4_576 ?
O2 Co1 O3 88.53(8) 3_567 4_576 ?
N1 Co1 O3 91.68(8) 1_455 4_576 ?
O4 Co1 Co1 94.86(6) 2_546 3_567 ?
O1 Co1 Co1 80.38(6) . 3_567 ?
O2 Co1 Co1 84.24(6) 3_567 3_567 ?
N1 Co1 Co1 161.32(6) 1_455 3_567 ?
O3 Co1 Co1 69.87(6) 4_576 3_567 ?
C11 N1 C12 116.8(2) . . ?
C11 N1 Co1 118.97(17) . 1_655 ?
C12 N1 Co1 124.26(17) . 1_655 ?
C11 N2 C10 115.5(3) . . ?
C1 O1 Co1 126.97(17) . . ?
C1 O2 Co1 122.03(17) . 3_567 ?
C5 O3 Co1 137.04(18) . 4_575 ?
C5 O4 Co1 111.54(17) . 2_556 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.068
