# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_xb1542_0m
_database_code_depnum_ccdc_archive 'CCDC 1864071'
_audit_update_record             
;
2018-08-27 deposited with the CCDC.	2020-06-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H3 Co N18'
_chemical_formula_sum            'C6 H3 Co N18'
_chemical_formula_weight         386.19

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.616(4)
_cell_length_b                   8.888(4)
_cell_length_c                   17.715(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.499(9)
_cell_angle_gamma                90
_cell_volume                     1347.9(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    631
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      21.87

_exptl_crystal_description       bulk
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.903
_exptl_crystal_F_000             1131
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    1.316
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6854
_diffrn_reflns_av_unetI/netI     0.0937
_diffrn_reflns_av_R_equivalents  0.0747
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.314
_diffrn_reflns_theta_max         25.604
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2530
_reflns_number_gt                1564
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0699P)²+0.0629P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2530
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1496
_refine_ls_wR_factor_gt          0.1249
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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_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 0.24353(9) 0.50738(8) 0.23901(4) 0.0201(2) Uani 1 1 d . . . . .
N1 N 0.2532(5) 0.6285(5) 0.3534(2) 0.0205(10) Uani 1 1 d . . . . .
N2 N 0.2901(6) 0.8631(5) 0.4203(2) 0.0295(12) Uani 1 1 d . . . . .
N3 N 0.1430(6) 0.6669(5) 0.4703(2) 0.0316(13) Uani 1 1 d . . . . .
N4 N 0.0928(7) 0.4512(5) 0.4069(3) 0.0360(14) Uani 1 1 d . . . . .
H4 H 0.0680 0.4206 0.4500 0.043 Uiso 1 1 calc R U . . .
N5 N -0.0398(7) 0.2389(5) 0.3561(3) 0.0352(14) Uani 1 1 d . . . . .
N6 N -0.0628(6) 0.1735(5) 0.2878(2) 0.0279(12) Uani 1 1 d . . . . .
N7 N 0.0136(6) 0.2473(5) 0.2392(2) 0.0271(11) Uani 1 1 d . . . . .
N8 N 0.0877(5) 0.3645(5) 0.2766(2) 0.0212(10) Uani 1 1 d . . . . .
N9 N 0.3967(6) 0.8349(5) 0.3127(2) 0.0281(12) Uani 1 1 d . . . . .
H9 H 0.4168 0.9285 0.3215 0.034 Uiso 1 1 calc R U . . .
N10 N 0.4080(5) 0.6571(5) 0.2116(2) 0.0225(11) Uani 1 1 d . . . . .
N11 N 0.5010(6) 0.6451(5) 0.1546(3) 0.0269(11) Uani 1 1 d . . . . .
N12 N 0.6007(6) 0.7559(5) 0.1606(3) 0.0289(12) Uani 1 1 d . . . . .
N13 N 0.5775(6) 0.8422(5) 0.2213(2) 0.0245(11) Uani 1 1 d . . . . .
N14 N 0.1897(7) 0.8872(5) 0.5353(3) 0.0381(14) Uani 1 1 d . . . . .
H14 H 0.1403 0.8435 0.5687 0.046 Uiso 1 1 calc R U . . .
N15 N 0.2896(7) 1.1292(5) 0.5036(3) 0.0395(14) Uani 1 1 d . . . . .
N16 N 0.3138(8) 1.2614(6) 0.5441(3) 0.0492(16) Uani 1 1 d . . . . .
N17 N 0.2807(7) 1.2371(5) 0.6128(3) 0.0396(14) Uani 1 1 d . . . . .
N18 N 0.2331(6) 1.0916(5) 0.6205(2) 0.0260(12) Uani 1 1 d . . . . .
C1 C 0.1688(7) 0.5884(6) 0.4089(3) 0.0263(14) Uani 1 1 d . . . . .
C2 C 0.3077(7) 0.7693(6) 0.3630(3) 0.0209(12) Uani 1 1 d . . . . .
C3 C 0.2096(8) 0.8040(6) 0.4722(3) 0.0306(15) Uani 1 1 d . . . . .
C4 C 0.0507(7) 0.3561(6) 0.3470(3) 0.0254(13) Uani 1 1 d . . . . .
C5 C 0.4600(7) 0.7779(6) 0.2507(3) 0.0225(13) Uani 1 1 d . . . . .
C6 C 0.2382(7) 1.0306(6) 0.5520(3) 0.0297(14) Uani 1 1 d . . . . .


_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 N8 2.016(4) . ?
Co1 N10 2.042(4) . ?
Co1 N6 2.160(5) 2 ?
Co1 N13 2.187(5) 2_645 ?
Co1 N18 2.268(4) 4_575 ?
Co1 N1 2.288(4) . ?
N1 C1 1.336(6) . ?
N1 C2 1.341(7) . ?
N2 C3 1.321(7) . ?
N2 C2 1.336(6) . ?
N3 C1 1.332(6) . ?
N3 C3 1.346(7) . ?
N4 C4 1.374(7) . ?
N4 C1 1.382(7) . ?
N5 C4 1.323(7) . ?
N5 N6 1.336(6) . ?
N6 N7 1.317(6) . ?
N6 Co1 2.160(5) 2_545 ?
N7 N8 1.354(6) . ?
N8 C4 1.324(6) . ?
N9 C2 1.369(6) . ?
N9 C5 1.378(6) . ?
N10 C5 1.327(6) . ?
N10 N11 1.362(6) . ?
N11 N12 1.304(6) . ?
N12 N13 1.354(6) . ?
N13 C5 1.320(6) . ?
N13 Co1 2.187(5) 2_655 ?
N14 C6 1.363(7) . ?
N14 C3 1.367(6) . ?
N15 C6 1.336(7) . ?
N15 N16 1.380(7) . ?
N16 N17 1.298(6) . ?
N17 N18 1.368(6) . ?
N18 C6 1.336(7) . ?
N18 Co1 2.268(4) 4_576 ?

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
N8 Co1 N10 174.49(17) . . ?
N8 Co1 N6 90.73(18) . 2 ?
N10 Co1 N6 90.26(18) . 2 ?
N8 Co1 N13 86.73(17) . 2_645 ?
N10 Co1 N13 91.76(18) . 2_645 ?
N6 Co1 N13 173.98(15) 2 2_645 ?
N8 Co1 N18 95.90(16) . 4_575 ?
N10 Co1 N18 89.38(16) . 4_575 ?
N6 Co1 N18 96.27(17) 2 4_575 ?
N13 Co1 N18 89.42(16) 2_645 4_575 ?
N8 Co1 N1 87.88(16) . . ?
N10 Co1 N1 86.96(16) . . ?
N6 Co1 N1 80.01(16) 2 . ?
N13 Co1 N1 94.44(16) 2_645 . ?
N18 Co1 N1 174.76(15) 4_575 . ?
C1 N1 C2 111.6(4) . . ?
C1 N1 Co1 123.9(4) . . ?
C2 N1 Co1 121.9(3) . . ?
C3 N2 C2 113.2(5) . . ?
C1 N3 C3 112.6(5) . . ?
C4 N4 C1 130.2(5) . . ?
C4 N5 N6 105.1(4) . . ?
N7 N6 N5 110.0(4) . . ?
N7 N6 Co1 126.7(3) . 2_545 ?
N5 N6 Co1 121.7(3) . 2_545 ?
N6 N7 N8 107.8(4) . . ?
C4 N8 N7 105.5(4) . . ?
C4 N8 Co1 125.9(4) . . ?
N7 N8 Co1 128.2(3) . . ?
C2 N9 C5 131.6(5) . . ?
C5 N10 N11 104.9(4) . . ?
C5 N10 Co1 127.3(3) . . ?
N11 N10 Co1 127.4(3) . . ?
N12 N11 N10 108.5(4) . . ?
N11 N12 N13 109.7(4) . . ?
C5 N13 N12 104.9(4) . . ?
C5 N13 Co1 135.1(4) . 2_655 ?
N12 N13 Co1 118.2(3) . 2_655 ?
C6 N14 C3 128.3(5) . . ?
C6 N15 N16 105.5(5) . . ?
N17 N16 N15 108.0(5) . . ?
N16 N17 N18 110.6(5) . . ?
C6 N18 N17 104.6(4) . . ?
C6 N18 Co1 133.0(4) . 4_576 ?
N17 N18 Co1 118.6(3) . 4_576 ?
N3 C1 N1 128.0(5) . . ?
N3 C1 N4 111.1(5) . . ?
N1 C1 N4 120.8(5) . . ?
N2 C2 N1 127.6(5) . . ?
N2 C2 N9 110.4(5) . . ?
N1 C2 N9 122.0(5) . . ?
N2 C3 N3 126.8(5) . . ?
N2 C3 N14 118.5(5) . . ?
N3 C3 N14 114.6(5) . . ?
N5 C4 N8 111.6(5) . . ?
N5 C4 N4 119.9(5) . . ?
N8 C4 N4 128.5(5) . . ?
N13 C5 N10 112.0(5) . . ?
N13 C5 N9 123.1(5) . . ?
N10 C5 N9 124.9(5) . . ?
N18 C6 N15 111.4(5) . . ?
N18 C6 N14 122.4(5) . . ?
N15 C6 N14 126.1(5) . . ?

_refine_diff_density_max         0.855
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.113



