# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_ic19482_5
_database_code_depnum_ccdc_archive 'CCDC 2098717'
loop_
_audit_author_name
_audit_author_address
'Gene-Hsiang Lee'
;Instrumentation Center, National Taiwan University
Taiwan
;
_audit_update_record             
;
2021-07-23 deposited with the CCDC.	2021-07-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H18 Co N2 O9'
_chemical_formula_weight         417.23

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'

_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                   18.8828(7)
_cell_length_b                   11.3176(4)
_cell_length_c                   8.0387(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.0405(14)
_cell_angle_gamma                90
_cell_volume                     1713.66(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8918
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      30.01

_exptl_crystal_description       needle
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_F_000             860
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.196
_exptl_crystal_size_mid          0.056
_exptl_crystal_size_min          0.046
_exptl_absorpt_coefficient_mu    1.054
_shelx_estimated_absorpt_T_min   0.820
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6515
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4887
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.814
_diffrn_reflns_theta_max         29.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4887
_reflns_number_gt                4632
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 _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. Completness statistics refer to single and 
 composite reflections containing twin component 1 only. 
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0110P)²+6.6363P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4887
_refine_ls_number_parameters     269
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0710
_refine_ls_wR_factor_ref         0.1329
_refine_ls_wR_factor_gt          0.1311
_refine_ls_goodness_of_fit_ref   1.306
_refine_ls_restrained_S_all      1.304
_refine_ls_shift/su_max          0.002
_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 1.000000 1.500000 0.500000 0.00730(16) Uani 1 2 d S . P . .
Co2 Co 0.500000 1.000000 0.000000 0.00686(16) Uani 1 2 d S . P . .
O1 O 0.96477(15) 1.5512(3) 0.7316(3) 0.0095(5) Uani 1 1 d . . . . .
O2 O 0.93006(17) 1.6503(3) 1.0881(4) 0.0122(6) Uani 1 1 d . . . . .
O3 O 0.45511(15) 1.0339(3) 0.2306(3) 0.0087(5) Uani 1 1 d . . . . .
O4 O 0.42611(16) 1.1438(3) 0.5881(4) 0.0124(6) Uani 1 1 d . . . . .
O5 O 1.04466(17) 1.3468(3) 0.5888(4) 0.0124(6) Uani 1 1 d D . . . .
H5A H 1.057(3) 1.292(3) 0.530(4) 0.019 Uiso 1 1 d D U . . .
H5B H 1.058(3) 1.335(4) 0.687(2) 0.019 Uiso 1 1 d D U . . .
O6 O 0.54447(18) 0.8432(3) 0.0863(4) 0.0140(6) Uani 1 1 d D . . . .
H6A H 0.562(3) 0.787(3) 0.035(5) 0.021 Uiso 1 1 d D U . . .
H6B H 0.558(3) 0.838(4) 0.187(2) 0.021 Uiso 1 1 d D U . . .
O7 O 0.6826(2) 0.6350(4) 0.2476(5) 0.0270(8) Uani 1 1 d D . . . .
H7A H 0.6403(12) 0.617(6) 0.254(7) 0.041 Uiso 1 1 d D U . . .
H7B H 0.697(3) 0.675(5) 0.330(5) 0.041 Uiso 1 1 d D U . . .
O8 O 0.7528(2) 0.7249(3) -0.0144(5) 0.0285(8) Uani 1 1 d D . . . .
H8A H 0.781(3) 0.766(5) 0.045(6) 0.043 Uiso 1 1 d D U . . .
H8B H 0.729(3) 0.685(5) 0.047(6) 0.043 Uiso 1 1 d D U . . .
O9 O 0.82209(19) 0.8691(4) 0.2214(5) 0.0255(8) Uani 1 1 d D . . . .
H9A H 0.8647(10) 0.881(6) 0.209(7) 0.038 Uiso 1 1 d D U . . .
H9B H 0.817(3) 0.842(6) 0.316(4) 0.038 Uiso 1 1 d D U . . .
N1 N 0.89961(18) 1.4051(3) 0.4246(4) 0.0102(6) Uani 1 1 d . . . . .
N2 N 0.59336(18) 1.0898(3) 0.1062(4) 0.0091(6) Uani 1 1 d . . . . .
C1 C 0.9858(2) 1.5223(3) 0.8782(5) 0.0069(7) Uani 1 1 d . U . . .
C2 C 0.9682(2) 1.5675(4) 1.0409(5) 0.0114(8) Uani 1 1 d . . . . .
C3 C 0.4794(2) 1.0159(3) 0.3778(4) 0.0060(7) Uani 1 1 d . U . . .
C4 C 0.4663(2) 1.0651(3) 0.5407(4) 0.0061(7) Uani 1 1 d . . . . .
C5 C 0.8442(2) 1.4598(4) 0.3424(5) 0.0136(8) Uani 1 1 d . . . . .
H5 H 0.846854 1.542753 0.325396 0.016 Uiso 1 1 calc R U . . .
C6 C 0.7834(2) 1.4005(4) 0.2813(5) 0.0141(8) Uani 1 1 d . . . . .
H6 H 0.745228 1.442906 0.226011 0.017 Uiso 1 1 calc R U . . .
C7 C 0.7786(2) 1.2779(4) 0.3017(5) 0.0110(8) Uani 1 1 d . . . . .
C8 C 0.8362(2) 1.2220(3) 0.3824(6) 0.0153(8) Uani 1 1 d . . . . .
H8 H 0.835846 1.138748 0.397529 0.018 Uiso 1 1 calc R U . . .
C9 C 0.8944(2) 1.2875(4) 0.4411(6) 0.0164(8) Uani 1 1 d . . . . .
H9 H 0.933190 1.246703 0.496639 0.020 Uiso 1 1 calc R U . . .
C10 C 0.6587(2) 1.0411(4) 0.1099(5) 0.0101(7) Uani 1 1 d . . . . .
H10 H 0.663005 0.963687 0.066059 0.012 Uiso 1 1 calc R U . . .
C11 C 0.7192(2) 1.0970(4) 0.1733(5) 0.0133(8) Uani 1 1 d . . . . .
H11 H 0.763834 1.058002 0.175056 0.016 Uiso 1 1 calc R U . . .
C12 C 0.7146(2) 1.2124(4) 0.2356(5) 0.0094(7) Uani 1 1 d . . . . .
C13 C 0.6469(2) 1.2643(3) 0.2290(5) 0.0128(8) Uani 1 1 d . . . . .
H13 H 0.641046 1.342777 0.267682 0.015 Uiso 1 1 calc R U . . .
C14 C 0.5894(2) 1.2005(4) 0.1660(5) 0.0120(7) Uani 1 1 d . . . . .
H14 H 0.543897 1.236597 0.164572 0.014 Uiso 1 1 calc R U . . .


_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 O5 2.035(3) . ?
Co1 O5 2.035(3) 3_786 ?
Co1 O1 2.102(3) 3_786 ?
Co1 O1 2.102(3) . ?
Co1 N1 2.225(3) 3_786 ?
Co1 N1 2.225(3) . ?
Co2 O6 2.062(3) 3_675 ?
Co2 O6 2.063(3) . ?
Co2 O3 2.126(3) 3_675 ?
Co2 O3 2.126(3) . ?
Co2 N2 2.158(3) 3_675 ?
Co2 N2 2.158(3) . ?
O1 C1 1.260(5) . ?
O2 C2 1.257(5) . ?
O3 C3 1.255(5) . ?
O4 C4 1.247(5) . ?
N1 C9 1.343(5) . ?
N1 C5 1.348(6) . ?
N2 C14 1.345(5) . ?
N2 C10 1.349(5) . ?
C1 C2 1.460(6) 3_787 ?
C1 C2 1.464(5) . ?
C3 C4 1.460(5) . ?
C3 C4 1.492(5) 3_676 ?
C5 C6 1.390(6) . ?
C6 C7 1.401(6) . ?
C7 C8 1.381(6) . ?
C7 C12 1.483(5) . ?
C8 C9 1.380(6) . ?
C10 C11 1.374(6) . ?
C11 C12 1.403(6) . ?
C12 C13 1.405(5) . ?
C13 C14 1.372(5) . ?

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
O5 Co1 O5 180.0 . 3_786 ?
O5 Co1 O1 85.80(12) . 3_786 ?
O5 Co1 O1 94.20(12) 3_786 3_786 ?
O5 Co1 O1 94.20(12) . . ?
O5 Co1 O1 85.80(12) 3_786 . ?
O1 Co1 O1 180.00(6) 3_786 . ?
O5 Co1 N1 89.51(13) . 3_786 ?
O5 Co1 N1 90.48(13) 3_786 3_786 ?
O1 Co1 N1 93.30(12) 3_786 3_786 ?
O1 Co1 N1 86.70(12) . 3_786 ?
O5 Co1 N1 90.49(13) . . ?
O5 Co1 N1 89.51(13) 3_786 . ?
O1 Co1 N1 86.70(12) 3_786 . ?
O1 Co1 N1 93.30(12) . . ?
N1 Co1 N1 180.00(9) 3_786 . ?
O6 Co2 O6 180.0 3_675 . ?
O6 Co2 O3 92.28(12) 3_675 3_675 ?
O6 Co2 O3 87.73(12) . 3_675 ?
O6 Co2 O3 87.73(12) 3_675 . ?
O6 Co2 O3 92.27(12) . . ?
O3 Co2 O3 180.0 3_675 . ?
O6 Co2 N2 88.31(13) 3_675 3_675 ?
O6 Co2 N2 91.69(13) . 3_675 ?
O3 Co2 N2 86.27(12) 3_675 3_675 ?
O3 Co2 N2 93.73(12) . 3_675 ?
O6 Co2 N2 91.69(13) 3_675 . ?
O6 Co2 N2 88.31(13) . . ?
O3 Co2 N2 93.73(12) 3_675 . ?
O3 Co2 N2 86.27(12) . . ?
N2 Co2 N2 180.0 3_675 . ?
C1 O1 Co1 131.2(3) . . ?
C3 O3 Co2 130.6(3) . . ?
C9 N1 C5 116.4(4) . . ?
C9 N1 Co1 121.2(3) . . ?
C5 N1 Co1 121.9(3) . . ?
C14 N2 C10 116.5(3) . . ?
C14 N2 Co2 121.0(3) . . ?
C10 N2 Co2 122.4(3) . . ?
O1 C1 C2 137.4(4) . 3_787 ?
O1 C1 C2 132.0(4) . . ?
C2 C1 C2 90.6(3) 3_787 . ?
O2 C2 C1 136.1(4) . 3_787 ?
O2 C2 C1 134.5(4) . . ?
C1 C2 C1 89.4(3) 3_787 . ?
O3 C3 C4 135.2(3) . . ?
O3 C3 C4 135.1(4) . 3_676 ?
C4 C3 C4 89.7(3) . 3_676 ?
O4 C4 C3 133.8(3) . . ?
O4 C4 C3 135.9(4) . 3_676 ?
C3 C4 C3 90.3(3) . 3_676 ?
N1 C5 C6 123.0(4) . . ?
C5 C6 C7 119.8(4) . . ?
C8 C7 C6 116.9(4) . . ?
C8 C7 C12 122.3(3) . . ?
C6 C7 C12 120.7(4) . . ?
C9 C8 C7 119.8(4) . . ?
N1 C9 C8 124.1(4) . . ?
N2 C10 C11 123.8(4) . . ?
C10 C11 C12 119.3(4) . . ?
C11 C12 C13 117.1(4) . . ?
C11 C12 C7 121.5(3) . . ?
C13 C12 C7 121.4(3) . . ?
C14 C13 C12 119.3(4) . . ?
N2 C14 C13 124.0(4) . . ?

_refine_diff_density_max         0.652
_refine_diff_density_min         -0.618
_refine_diff_density_rms         0.103

