# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# 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_vnu10-sr
_database_code_depnum_ccdc_archive 'CCDC 1063411'
_audit_update_record             
;
2015-05-06 deposited with the CCDC.
2015-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        VNU-10
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H10 Co N O4'
_chemical_formula_weight         279.13

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'
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'
Co Co -2.3653 3.6143 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Hexagonal
_symmetry_space_group_name_H-M   p6/mmm

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

_cell_length_a                   21.5645(7)
_cell_length_b                   21.5645(7)
_cell_length_c                   9.4379(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     3800.9(2)
_cell_formula_units_Z            6
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.732
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             852
_exptl_absorpt_coefficient_mu    5.333
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5341
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_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_reflns_number            25049
_diffrn_reflns_av_R_equivalents  0.1281
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         65.15
_reflns_number_total             1315
_reflns_number_gt                1123
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          SQUEEZE
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 -0.012 -0.010 -0.019 2476 725 ' '
_platon_squeeze_details          
;
;

_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)+(0.0660P)²+3.8740P] 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         1315
_refine_ls_number_parameters     55
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1456
_refine_ls_wR_factor_gt          0.1390
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_restrained_S_all      1.130
_refine_ls_shift/su_max          0.093
_refine_ls_shift/su_mean         0.009

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
H3 H -0.0850(12) 0.4167(11) 0.101(4) 0.049(11) Uiso 1 1 d D . .
C3 C -0.0761(6) 0.4620(3) 0.0809(10) 0.0530(18) Uani 0.50 2 d SPD . .
C6 C -0.0371(5) 0.4260(5) 0.0812(7) 0.0530(18) Uani 0.50 1 d PD . .
Co1 Co 0.0000 0.5000 0.35855(8) 0.0234(3) Uani 1 4 d S . .
H1 H 0.0000 0.418(2) 0.097(4) 0.021(11) Uiso 1 2 d S . .
N1 N 0.0000 0.5000 0.1372(4) 0.0262(11) Uani 1 4 d S . .
O1 O 0.07648(12) 0.47305(15) 0.3818(2) 0.0429(6) Uani 1 1 d . . .
C2 C 0.19836(18) 0.4603(2) 0.3739(3) 0.0434(9) Uani 1 1 d . . .
H2 H 0.1764 0.4599 0.2864 0.052 Uiso 1 1 calc R . .
C5 C 0.1016(2) 0.4690(2) 0.5000 0.0310(10) Uani 1 2 d S . .
C7 C 0.1659(2) 0.4608(3) 0.5000 0.0315(10) Uani 1 2 d S . .

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
C3 0.051(4) 0.080(4) 0.018(3) -0.0013(14) -0.003(3) 0.026(2)
C6 0.051(4) 0.080(4) 0.018(3) -0.0013(14) -0.003(3) 0.026(2)
Co1 0.0130(4) 0.0417(5) 0.0058(5) 0.000 0.000 0.0065(2)
N1 0.019(2) 0.043(2) 0.009(2) 0.000 0.000 0.0094(11)
O1 0.0364(12) 0.0892(18) 0.0139(10) 0.0006(11) -0.0003(9) 0.0395(13)
C2 0.0427(19) 0.086(3) 0.0120(16) -0.0033(16) -0.0039(13) 0.040(2)
C5 0.026(2) 0.047(3) 0.013(2) 0.000 0.000 0.013(2)
C7 0.032(2) 0.052(3) 0.0123(19) 0.000 0.000 0.022(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
C3 C6 1.401(11) . ?
C3 C6 1.401(11) 21_565 ?
C3 N1 1.517(11) . ?
C3 C3 1.526(19) 16 ?
C6 C6 1.384(18) 24 ?
C6 N1 1.480(9) . ?
C6 C6 1.532(13) 16 ?
C6 C6 2.065(16) 9 ?
Co1 O1 2.016(2) . ?
Co1 O1 2.016(2) 21_565 ?
Co1 O1 2.016(2) 24 ?
Co1 O1 2.016(2) 4_565 ?
Co1 N1 2.089(4) . ?
Co1 Co1 2.6700(15) 13_566 ?
N1 C6 1.480(9) 4_565 ?
N1 C6 1.480(9) 24 ?
N1 C6 1.480(9) 21_565 ?
N1 C3 1.517(11) 4_565 ?
O1 C5 1.261(3) . ?
C2 C2 1.370(6) 20 ?
C2 C7 1.384(4) . ?
C5 O1 1.261(3) 16_556 ?
C5 C7 1.484(6) . ?
C7 C2 1.384(4) 16_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
C6 C3 C6 117.3(11) . 21_565 ?
C6 C3 N1 60.8(5) . . ?
C6 C3 N1 60.8(5) 21_565 . ?
C6 C3 C3 90.1(5) . 16 ?
C6 C3 C3 90.1(5) 21_565 16 ?
N1 C3 C3 110.5(4) . 16 ?
C6 C6 C3 121.3(5) 24 . ?
C6 C6 N1 62.1(4) 24 . ?
C3 C6 N1 63.5(6) . . ?
C6 C6 C6 90.001(1) 24 16 ?
C3 C6 C6 89.9(5) . 16 ?
N1 C6 C6 110.9(3) . 16 ?
C6 C6 C6 47.9(4) 24 9 ?
C3 C6 C6 110.3(5) . 9 ?
N1 C6 C6 87.2(5) . 9 ?
C6 C6 C6 42.1(4) 16 9 ?
O1 Co1 O1 88.41(16) . 21_565 ?
O1 Co1 O1 90.22(16) . 24 ?
O1 Co1 O1 167.48(12) 21_565 24 ?
O1 Co1 O1 167.48(12) . 4_565 ?
O1 Co1 O1 90.22(15) 21_565 4_565 ?
O1 Co1 O1 88.41(16) 24 4_565 ?
O1 Co1 N1 96.26(6) . . ?
O1 Co1 N1 96.26(6) 21_565 . ?
O1 Co1 N1 96.26(6) 24 . ?
O1 Co1 N1 96.26(6) 4_565 . ?
O1 Co1 Co1 83.74(6) . 13_566 ?
O1 Co1 Co1 83.74(6) 21_565 13_566 ?
O1 Co1 Co1 83.74(6) 24 13_566 ?
O1 Co1 Co1 83.74(6) 4_565 13_566 ?
N1 Co1 Co1 180.000(1) . 13_566 ?
C6 N1 C6 138.1(6) 4_565 . ?
C6 N1 C6 107.9(7) 4_565 24 ?
C6 N1 C6 55.8(7) . 24 ?
C6 N1 C6 55.8(7) 4_565 21_565 ?
C6 N1 C6 107.9(7) . 21_565 ?
C6 N1 C6 138.1(6) 24 21_565 ?
C6 N1 C3 108.2(4) 4_565 . ?
C6 N1 C3 55.7(4) . . ?
C6 N1 C3 108.2(4) 24 . ?
C6 N1 C3 55.7(4) 21_565 . ?
C6 N1 C3 55.7(4) 4_565 4_565 ?
C6 N1 C3 108.2(4) . 4_565 ?
C6 N1 C3 55.7(4) 24 4_565 ?
C6 N1 C3 108.2(4) 21_565 4_565 ?
C3 N1 C3 139.0(8) . 4_565 ?
C6 N1 Co1 110.9(3) 4_565 . ?
C6 N1 Co1 110.9(3) . . ?
C6 N1 Co1 110.9(3) 24 . ?
C6 N1 Co1 110.9(3) 21_565 . ?
C3 N1 Co1 110.5(4) . . ?
C3 N1 Co1 110.5(4) 4_565 . ?
C5 O1 Co1 123.9(2) . . ?
C2 C2 C7 120.7(2) 20 . ?
O1 C5 O1 124.3(4) 16_556 . ?
O1 C5 C7 117.8(2) 16_556 . ?
O1 C5 C7 117.8(2) . . ?
C2 C7 C2 118.6(4) 16_556 . ?
C2 C7 C5 120.5(2) 16_556 . ?
C2 C7 C5 120.5(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        65.15
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.322
_refine_diff_density_min         -1.135
_refine_diff_density_rms         0.055
