# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_p
_database_code_depnum_ccdc_archive 'CCDC 1483259'
_audit_update_record             
;
2016-06-02 deposited with the CCDC.
2016-07-27 downloaded from the CCDC.
;
_audit_creation_date             2016-06-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H11 Co N7 O6'
_chemical_formula_sum            'C18 H11 Co N7 O6'
_chemical_formula_weight         480.27
_chemical_melting_point          ?
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'
Co Co 0.3494 0.9721 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.131(2)
_cell_length_b                   19.071(4)
_cell_length_c                   20.791(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4017.1(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3738
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.387
_cell_measurement_theta_min      2.478
_shelx_estimated_absorpt_T_max   0.931
_shelx_estimated_absorpt_T_min   0.923
_exptl_absorpt_coefficient_mu    0.907
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1944
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            21881
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.476
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2687
_reflns_number_total             3530
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3530
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0340P)²+2.6120P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0933
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C9(H9), C10(H10), C11(H11), C13(H13), C15(H15),
 C16(H16), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.58046(3) 0.55103(2) 0.43992(2) 0.02595(13) Uani 1 1 d . . . . .
O1 O 0.40685(17) 0.50216(9) 0.44990(10) 0.0318(5) Uani 1 1 d . . . . .
O2 O 0.29218(19) 0.59749(10) 0.42064(11) 0.0398(5) Uani 1 1 d . . . . .
O3 O -0.19916(19) 0.57263(11) 0.43054(11) 0.0426(6) Uani 1 1 d . . . . .
O4 O -0.28772(18) 0.46841(10) 0.42397(10) 0.0358(5) Uani 1 1 d . . . . .
O5 O 0.0006(3) 0.27476(13) 0.3548(2) 0.1087(13) Uani 1 1 d . . . . .
O6 O 0.2094(3) 0.28552(14) 0.35708(17) 0.0915(11) Uani 1 1 d . . . . .
N1 N 0.5683(2) 0.57356(12) 0.34109(12) 0.0352(6) Uani 1 1 d . . . . .
N2 N 0.5246(2) 0.62679(12) 0.24983(12) 0.0341(6) Uani 1 1 d . . . . .
N3 N 0.3534(3) 0.70272(14) 0.22784(13) 0.0468(7) Uani 1 1 d . . . . .
N4 N 0.3525(3) 0.77697(14) 0.13568(13) 0.0445(7) Uani 1 1 d . . . . .
N5 N 0.5214(2) 0.77630(11) 0.06105(11) 0.0330(6) Uani 1 1 d . . . . .
N6 N 0.5672(2) 0.85489(11) -0.01281(11) 0.0296(5) Uani 1 1 d . . . . .
N7 N 0.0998(3) 0.30820(15) 0.36596(16) 0.0580(9) Uani 1 1 d . . . . .
C1 C 0.0846(3) 0.38075(14) 0.38813(15) 0.0369(7) Uani 1 1 d . . . . .
C2 C -0.0409(3) 0.40688(14) 0.39528(14) 0.0329(7) Uani 1 1 d . . . . .
H2 H -0.1145 0.3788 0.3880 0.040 Uiso 1 1 calc R . . . .
C3 C -0.0543(2) 0.47661(14) 0.41377(13) 0.0263(6) Uani 1 1 d . . . . .
C4 C 0.0571(2) 0.51694(14) 0.42435(13) 0.0265(6) Uani 1 1 d . . . . .
H4 H 0.0474 0.5640 0.4353 0.032 Uiso 1 1 calc R . . . .
C5 C 0.1829(3) 0.48883(14) 0.41901(13) 0.0261(6) Uani 1 1 d . . . . .
C6 C 0.1967(3) 0.41924(15) 0.40077(14) 0.0341(7) Uani 1 1 d . . . . .
H6 H 0.2799 0.3990 0.3971 0.041 Uiso 1 1 calc R . . . .
C7 C 0.3015(3) 0.53425(15) 0.43059(13) 0.0290(6) Uani 1 1 d . . . . .
C8 C -0.1883(3) 0.50791(15) 0.42290(13) 0.0293(7) Uani 1 1 d . . . . .
C9 C 0.4949(3) 0.62028(14) 0.31356(14) 0.0333(7) Uani 1 1 d . . . . .
H9 H 0.4301 0.6462 0.3346 0.040 Uiso 1 1 calc R . . . .
C10 C 0.6503(4) 0.54758(17) 0.29248(16) 0.0494(9) Uani 1 1 d . . . . .
H10 H 0.7133 0.5126 0.2980 0.059 Uiso 1 1 calc R . . . .
C11 C 0.6252(4) 0.58015(17) 0.23721(16) 0.0475(9) Uani 1 1 d . . . . .
H11 H 0.6670 0.5729 0.1980 0.057 Uiso 1 1 calc R . . . .
C12 C 0.4674(3) 0.67659(14) 0.20789(14) 0.0331(7) Uani 1 1 d . . . . .
C13 C 0.5303(3) 0.69690(14) 0.15237(14) 0.0334(7) Uani 1 1 d . . . . .
H13 H 0.6099 0.6774 0.1391 0.040 Uiso 1 1 calc R . . . .
C14 C 0.4665(3) 0.74839(14) 0.11795(14) 0.0319(7) Uani 1 1 d . . . . .
C15 C 0.3030(3) 0.75180(19) 0.19005(18) 0.0535(9) Uani 1 1 d . . . . .
H15 H 0.2231 0.7710 0.2033 0.064 Uiso 1 1 calc R . . . .
C16 C 0.4900(3) 0.84002(13) 0.03536(14) 0.0303(6) Uani 1 1 d . . . . .
H16 H 0.4226 0.8689 0.0502 0.036 Uiso 1 1 calc R . . . .
C17 C 0.6250(3) 0.74994(15) 0.02542(16) 0.0442(8) Uani 1 1 d . . . . .
H17 H 0.6680 0.7073 0.0314 0.053 Uiso 1 1 calc R . . . .
C18 C 0.6509(3) 0.79836(15) -0.01943(16) 0.0432(8) Uani 1 1 d . . . . .
H18 H 0.7162 0.7944 -0.0507 0.052 Uiso 1 1 calc R . . . .


_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 2.0013(18) . ?
Co1 O3 2.279(2) 1_655 ?
Co1 O4 2.092(2) 1_655 ?
Co1 N1 2.103(2) . ?
Co1 N6 2.050(2) 8_576 ?
Co1 C8 2.508(3) 1_655 ?
O1 C7 1.294(3) . ?
O2 C7 1.227(3) . ?
O3 Co1 2.279(2) 1_455 ?
O3 C8 1.249(3) . ?
O4 Co1 2.092(2) 1_455 ?
O4 C8 1.258(3) . ?
O5 N7 1.212(4) . ?
O6 N7 1.206(3) . ?
N1 C9 1.294(3) . ?
N1 C10 1.399(4) . ?
N2 C9 1.364(4) . ?
N2 C11 1.377(4) . ?
N2 C12 1.414(4) . ?
N3 C12 1.325(4) . ?
N3 C15 1.324(4) . ?
N4 C14 1.330(4) . ?
N4 C15 1.326(4) . ?
N5 C14 1.411(4) . ?
N5 C16 1.365(3) . ?
N5 C17 1.380(4) . ?
N6 Co1 2.050(2) 8_575 ?
N6 C16 1.302(3) . ?
N6 C18 1.378(3) . ?
N7 C1 1.466(4) . ?
C1 C2 1.374(4) . ?
C1 C6 1.377(4) . ?
C2 C3 1.391(4) . ?
C3 C4 1.383(4) . ?
C3 C8 1.495(4) . ?
C4 C5 1.387(4) . ?
C5 C6 1.387(4) . ?
C5 C7 1.501(4) . ?
C8 Co1 2.508(3) 1_455 ?
C10 C11 1.331(4) . ?
C12 C13 1.374(4) . ?
C13 C14 1.376(4) . ?
C17 C18 1.338(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
O1 Co1 O3 162.58(7) . 1_655 ?
O1 Co1 O4 103.10(7) . 1_655 ?
O1 Co1 N1 98.35(9) . . ?
O1 Co1 N6 107.48(8) . 8_576 ?
O1 Co1 C8 133.07(9) . 1_655 ?
O3 Co1 C8 29.76(8) 1_655 1_655 ?
O4 Co1 O3 59.81(7) 1_655 1_655 ?
O4 Co1 N1 92.08(8) 1_655 . ?
O4 Co1 C8 30.04(8) 1_655 1_655 ?
N1 Co1 O3 86.37(9) . 1_655 ?
N1 Co1 C8 89.06(9) . 1_655 ?
N6 Co1 O3 86.96(8) 8_576 1_655 ?
N6 Co1 O4 140.98(8) 8_576 1_655 ?
N6 Co1 N1 106.61(9) 8_576 . ?
N6 Co1 C8 114.56(9) 8_576 1_655 ?
C7 O1 Co1 118.18(17) . . ?
C8 O3 Co1 85.35(16) . 1_455 ?
C8 O4 Co1 93.61(17) . 1_455 ?
C9 N1 Co1 127.3(2) . . ?
C9 N1 C10 105.4(3) . . ?
C10 N1 Co1 126.8(2) . . ?
C9 N2 C11 106.8(2) . . ?
C9 N2 C12 124.7(2) . . ?
C11 N2 C12 128.3(3) . . ?
C15 N3 C12 114.6(3) . . ?
C15 N4 C14 114.6(3) . . ?
C16 N5 C14 124.9(2) . . ?
C16 N5 C17 107.0(2) . . ?
C17 N5 C14 127.7(2) . . ?
C16 N6 Co1 126.76(18) . 8_575 ?
C16 N6 C18 106.0(2) . . ?
C18 N6 Co1 126.61(19) . 8_575 ?
O5 N7 C1 118.0(3) . . ?
O6 N7 O5 123.0(3) . . ?
O6 N7 C1 118.9(3) . . ?
C2 C1 N7 118.2(3) . . ?
C2 C1 C6 123.3(3) . . ?
C6 C1 N7 118.5(3) . . ?
C1 C2 C3 117.8(2) . . ?
C2 C3 C8 120.4(2) . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 C8 119.9(2) . . ?
C3 C4 C5 121.5(2) . . ?
C4 C5 C6 119.0(2) . . ?
C4 C5 C7 120.0(2) . . ?
C6 C5 C7 121.0(2) . . ?
C1 C6 C5 118.6(2) . . ?
O1 C7 C5 115.9(2) . . ?
O2 C7 O1 125.5(2) . . ?
O2 C7 C5 118.6(2) . . ?
O3 C8 Co1 64.89(14) . 1_455 ?
O3 C8 O4 121.2(2) . . ?
O3 C8 C3 119.4(2) . . ?
O4 C8 Co1 56.35(14) . 1_455 ?
O4 C8 C3 119.4(2) . . ?
C3 C8 Co1 175.6(2) . 1_455 ?
N1 C9 N2 111.4(3) . . ?
C11 C10 N1 110.2(3) . . ?
C10 C11 N2 106.2(3) . . ?
N3 C12 N2 114.7(3) . . ?
N3 C12 C13 124.1(3) . . ?
C13 C12 N2 121.2(3) . . ?
C12 C13 C14 114.8(3) . . ?
N4 C14 N5 114.8(2) . . ?
N4 C14 C13 123.8(3) . . ?
C13 C14 N5 121.3(3) . . ?
N3 C15 N4 128.1(3) . . ?
N6 C16 N5 110.8(2) . . ?
C18 C17 N5 105.8(2) . . ?
C17 C18 N6 110.5(3) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
