# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1851327'
_audit_update_record             
;
2018-08-02 deposited with the CCDC.
2018-08-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 Co N O5, 1.5H2O'
_chemical_formula_sum            'C14 H12 Co N O6.50'
_chemical_formula_weight         357.18

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'
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           trigonal
_symmetry_space_group_name_H-M   'R -3 c :H'
_space_group_name_Hall           '-R 3 2"c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'

_cell_length_a                   18.1126(9)
_cell_length_b                   18.1126(9)
_cell_length_c                   46.624(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     13246.5(14)
_cell_formula_units_Z            36
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1552
_cell_measurement_theta_min      3.3161
_cell_measurement_theta_max      29.0662

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             6552
_exptl_absorpt_coefficient_mu    1.198
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.826
_exptl_absorpt_correction_T_max  0.866
_exptl_absorpt_process_details   ?

_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  'Oxford Diffraction Gemini R Ultra'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 10.0
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8301
_diffrn_reflns_av_R_equivalents  0.0716
_diffrn_reflns_av_sigmaI/netI    0.0795
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_theta_min         3.45
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2606
_reflns_number_gt                1822
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2006)'
_computing_cell_refinement       CrysAlis
_computing_data_reduction        CrysAlis
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 2σ(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.

For C4, C10, and C12 atoms, some anisotropic displacement ellipsoids were rather 
elongated which led us to use the ISOR restraint.
For c5 atom, SIMU restraint was used to make them behave similar anisotropic displacement parameters.
;

_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)+(0.0815P)²+39.3485P] 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         2606
_refine_ls_number_parameters     227
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.0945
_refine_ls_R_factor_gt           0.0661
_refine_ls_wR_factor_ref         0.1737
_refine_ls_wR_factor_gt          0.1577
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.000
_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
Co1 Co 0.19821(5) 0.11269(5) 0.017202(15) 0.0306(3) Uani 1 1 d . . .
C1 C 0.1452(4) 0.0775(3) -0.04356(11) 0.0317(13) Uani 1 1 d . . .
C2 C 0.1818(5) 0.0598(4) -0.07026(13) 0.0555(19) Uani 1 1 d . . .
C3 C 0.2102(8) 0.1206(5) -0.09144(16) 0.124(5) Uani 1 1 d . . .
H3 H 0.2015 0.1669 -0.0900 0.149 Uiso 1 1 calc R . .
C4 C 0.2524(8) 0.1120(6) -0.1154(2) 0.124(4) Uani 1 1 d U . .
H4 H 0.2736 0.1538 -0.1295 0.149 Uiso 1 1 calc R . .
C5 C 0.2620(8) 0.0449(6) -0.1177(2) 0.130(4) Uani 1 1 d U A .
H5 H 0.2908 0.0405 -0.1336 0.156 Uiso 1 1 calc R . .
C6 C 0.1964(4) -0.0104(3) -0.07250(12) 0.0438(16) Uani 1 1 d D A .
C7 C 0.2423(4) -0.0904(5) -0.10279(16) 0.073(3) Uani 1 1 d . A .
H7A H 0.2552 -0.1070 -0.0845 0.088 Uiso 1 1 calc R . .
H7B H 0.2903 -0.0748 -0.1155 0.088 Uiso 1 1 calc R . .
C8 C 0.1646(4) -0.1650(4) -0.11530(18) 0.059(2) Uani 1 1 d . . .
C11 C 0.0256(4) -0.3105(4) -0.13907(15) 0.0462(16) Uani 1 1 d . . .
C9 C 0.1271(16) -0.1631(13) -0.1381(6) 0.058(6) Uani 0.453(14) 1 d P A 1
H9 H 0.1497 -0.1119 -0.1481 0.069 Uiso 0.453(14) 1 calc PR A 1
C10 C 0.0575(16) -0.2302(19) -0.1486(6) 0.044(6) Uani 0.453(14) 1 d PU A 1
H10 H 0.0291 -0.2209 -0.1635 0.053 Uiso 0.453(14) 1 calc PR A 1
C12 C 0.0559(11) -0.3149(9) -0.1102(4) 0.055(5) Uani 0.453(14) 1 d PU A 1
H12 H 0.0281 -0.3650 -0.0996 0.066 Uiso 0.453(14) 1 calc PR A 1
C13 C 0.1262(9) -0.2438(9) -0.0989(3) 0.052(5) Uani 0.453(14) 1 d P A 1
H13 H 0.1484 -0.2464 -0.0812 0.062 Uiso 0.453(14) 1 calc PR A 1
C9' C 0.0989(13) -0.1592(13) -0.1300(5) 0.071(6) Uani 0.547(14) 1 d P A 2
H9' H 0.1006 -0.1071 -0.1314 0.085 Uiso 0.547(14) 1 calc PR A 2
C10' C 0.0304(13) -0.2339(15) -0.1426(6) 0.062(7) Uani 0.547(14) 1 d P A 2
H10' H -0.0111 -0.2300 -0.1532 0.075 Uiso 0.547(14) 1 calc PR A 2
C12' C 0.0992(10) -0.3114(9) -0.1318(3) 0.068(5) Uani 0.547(14) 1 d P A 2
H12' H 0.1036 -0.3600 -0.1344 0.082 Uiso 0.547(14) 1 calc PR A 2
C13' C 0.1673(9) -0.2361(9) -0.1201(4) 0.077(5) Uani 0.547(14) 1 d P A 2
H13' H 0.2172 -0.2361 -0.1155 0.092 Uiso 0.547(14) 1 calc PR A 2
C14 C -0.0486(4) -0.3900(4) -0.15065(14) 0.0393(14) Uani 1 1 d . A .
N1 N 0.2321(4) -0.0160(3) -0.09842(13) 0.077(2) Uani 1 1 d U . .
O1 O 0.1471(2) 0.0415(2) -0.02040(7) 0.0314(9) Uani 1 1 d . . .
O2 O 0.1184(3) 0.1275(3) -0.04565(8) 0.0427(10) Uani 1 1 d . . .
O3 O -0.1098(3) -0.3847(2) -0.16044(9) 0.0408(10) Uani 1 1 d . . .
O4 O -0.0421(2) -0.4562(2) -0.14944(10) 0.0502(11) Uani 1 1 d . . .
O5 O 0.1792(3) -0.0666(3) -0.05515(9) 0.0456(11) Uani 1 1 d D . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 O4 2.037(4) 36_545 ?
Co1 O1 2.066(4) 21 ?
Co1 O5 2.070(4) 21 ?
Co1 O1 2.098(3) . ?
Co1 O3 2.116(4) 10_554 ?
Co1 O2 2.126(4) 20 ?
C1 O2 1.227(7) . ?
C1 O1 1.271(6) . ?
C1 C2 1.518(8) . ?
C2 C3 1.374(10) . ?
C2 C6 1.426(9) . ?
C3 C4 1.404(13) . ?
C3 H3 0.9300 . ?
C4 C5 1.316(14) . ?
C4 H4 0.9300 . ?
C5 N1 1.313(11) . ?
C5 H5 0.9300 . ?
C6 O5 1.213(6) . ?
C6 N1 1.398(7) . ?
C7 N1 1.462(10) . ?
C7 C8 1.498(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.27(3) . ?
C8 C13' 1.332(16) . ?
C8 C9' 1.42(3) . ?
C8 C13 1.454(17) . ?
C11 C10 1.34(3) . ?
C11 C10' 1.36(3) . ?
C11 C12' 1.384(16) . ?
C11 C12 1.472(17) . ?
C11 C14 1.495(8) . ?
C9 C10 1.33(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C12 C13 1.384(19) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C9' C10' 1.43(3) . ?
C9' H9' 0.9300 . ?
C10' H10' 0.9300 . ?
C12' C13' 1.413(18) . ?
C12' H12' 0.9300 . ?
C13' H13' 0.9300 . ?
C14 O3 1.246(7) . ?
C14 O4 1.264(7) . ?
O1 Co1 2.066(4) 20 ?
O2 Co1 2.126(4) 21 ?
O3 Co1 2.116(4) 10_444 ?
O4 Co1 2.037(4) 30_445 ?
O5 Co1 2.070(4) 20 ?

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
O4 Co1 O1 175.72(17) 36_545 21 ?
O4 Co1 O5 90.10(17) 36_545 21 ?
O1 Co1 O5 85.83(15) 21 21 ?
O4 Co1 O1 89.94(16) 36_545 . ?
O1 Co1 O1 94.08(17) 21 . ?
O5 Co1 O1 177.97(16) 21 . ?
O4 Co1 O3 88.13(16) 36_545 10_554 ?
O1 Co1 O3 93.21(15) 21 10_554 ?
O5 Co1 O3 89.82(16) 21 10_554 ?
O1 Co1 O3 92.21(15) . 10_554 ?
O4 Co1 O2 88.14(17) 36_545 20 ?
O1 Co1 O2 90.00(15) 21 20 ?
O5 Co1 O2 82.65(16) 21 20 ?
O1 Co1 O2 95.32(15) . 20 ?
O3 Co1 O2 171.59(15) 10_554 20 ?
O2 C1 O1 124.7(5) . . ?
O2 C1 C2 117.8(5) . . ?
O1 C1 C2 117.5(5) . . ?
C3 C2 C6 120.0(6) . . ?
C3 C2 C1 116.6(6) . . ?
C6 C2 C1 123.0(5) . . ?
C2 C3 C4 119.2(9) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 120.0(9) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
N1 C5 C4 121.9(8) . . ?
N1 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
O5 C6 N1 116.8(6) . . ?
O5 C6 C2 127.9(5) . . ?
N1 C6 C2 115.2(6) . . ?
N1 C7 C8 113.0(7) . . ?
N1 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
N1 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C13' 99.3(13) . . ?
C9 C8 C9' 28.0(9) . . ?
C13' C8 C9' 115.2(11) . . ?
C9 C8 C13 117.8(12) . . ?
C13' C8 C13 50.9(9) . . ?
C9' C8 C13 108.6(11) . . ?
C9 C8 C7 125.1(12) . . ?
C13' C8 C7 117.8(9) . . ?
C9' C8 C7 124.3(10) . . ?
C13 C8 C7 117.0(9) . . ?
C10 C11 C10' 23.1(13) . . ?
C10 C11 C12' 101.5(13) . . ?
C10' C11 C12' 118.2(11) . . ?
C10 C11 C12 113.0(14) . . ?
C10' C11 C12 109.3(13) . . ?
C12' C11 C12 52.1(8) . . ?
C10 C11 C14 128.0(13) . . ?
C10' C11 C14 120.6(11) . . ?
C12' C11 C14 118.9(7) . . ?
C12 C11 C14 117.3(8) . . ?
C8 C9 C10 124(2) . . ?
C8 C9 H9 118.1 . . ?
C10 C9 H9 118.1 . . ?
C9 C10 C11 124(2) . . ?
C9 C10 H10 117.8 . . ?
C11 C10 H10 117.8 . . ?
C13 C12 C11 119.5(13) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C8 118.7(12) . . ?
C12 C13 H13 120.7 . . ?
C8 C13 H13 120.7 . . ?
C8 C9' C10' 119.4(18) . . ?
C8 C9' H9' 120.3 . . ?
C10' C9' H9' 120.3 . . ?
C11 C10' C9' 120(2) . . ?
C11 C10' H10' 120.0 . . ?
C9' C10' H10' 120.0 . . ?
C11 C12' C13' 117.6(12) . . ?
C11 C12' H12' 121.2 . . ?
C13' C12' H12' 121.2 . . ?
C8 C13' C12' 124.2(14) . . ?
C8 C13' H13' 117.9 . . ?
C12' C13' H13' 117.9 . . ?
O3 C14 O4 126.7(5) . . ?
O3 C14 C11 117.6(5) . . ?
O4 C14 C11 115.7(5) . . ?
C5 N1 C6 122.9(7) . . ?
C5 N1 C7 119.3(6) . . ?
C6 N1 C7 117.6(6) . . ?
C1 O1 Co1 124.2(3) . 20 ?
C1 O1 Co1 120.8(3) . . ?
Co1 O1 Co1 114.78(16) 20 . ?
C1 O2 Co1 136.8(4) . 21 ?
C14 O3 Co1 134.1(4) . 10_444 ?
C14 O4 Co1 129.6(4) . 30_445 ?
C6 O5 Co1 126.4(4) . 20 ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.881
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.098

# 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 0.000 0.250 424 78 ' '
2 0.000 0.000 0.750 424 78 ' '
3 0.333 0.667 0.417 424 78 ' '
4 0.333 0.667 0.917 424 78 ' '
5 0.667 0.333 0.083 424 78 ' '
6 0.667 0.333 0.583 424 78 ' '
_platon_squeeze_details          
;
;

