# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_20171012zqn2_0m_b
_database_code_depnum_ccdc_archive 'CCDC 1949664'
loop_
_audit_author_name
_audit_author_address
'Jie Zhang'
;North University of China
China
;
_audit_update_record             
;
2019-09-02 deposited with the CCDC.	2019-09-09 downloaded from the CCDC.
;
_audit_creation_date             2019-09-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H14 Co2 N4 O8, O4 S, 2(H2 O)'
_chemical_formula_sum            'C10 H18 Co2 N4 O14 S'
_chemical_formula_weight         568.20
_chemical_absolute_configuration .
_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'
S S 0.1246 0.1234 '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      tetragonal
_space_group_IT_number           114
_space_group_name_H-M_alt        'P -4 21 c'
_space_group_name_Hall           'P -4 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'y, -x, -z'
'-x, -y, z'
'-y, x, -z'
'x+1/2, -y+1/2, -z+1/2'
'-y+1/2, -x+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'y+1/2, x+1/2, z+1/2'

_cell_length_a                   9.5941(13)
_cell_length_b                   9.5941(13)
_cell_length_c                   20.329(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1871.2(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3740
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.94
_cell_measurement_theta_min      2.35
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.969
_exptl_absorpt_correction_T_max  0.9805
_exptl_absorpt_correction_T_min  0.7174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SABABS
_exptl_absorpt_special_details   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.017
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            13936
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.419
_diffrn_reflns_theta_min         2.347
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                1926
_reflns_number_total             2098
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SAINT (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.844
_refine_diff_density_min         -0.639
_refine_diff_density_rms         0.110
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.20(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.194
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         2098
_refine_ls_number_restraints     131
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0557
_refine_ls_restrained_S_all      1.162
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0158P)²+9.1256P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1205
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.80(5)
 0.20(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H,H) groups
3. Restrained distances
 H2A-H2B
 1.38 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(N4) \\sim Ueq, Uanis(C2) \\sim
Ueq, Uanis(N3) \\sim Ueq, Uanis(C4) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 Co1, Co2, O2, O5, O6, N3, N4, C1, C2, C3, C4, C5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6.a Riding coordinates:
 O1(H1A,H1B), O2(H2A,H2B), O10(H10A,H10B)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.500000 0.000000 -0.01199(6) 0.0193(3) Uani 1 2 d S TU P . .
Co2 Co 0.500000 0.500000 0.13137(6) 0.0222(3) Uani 1 2 d S TU P . .
S1 S 0.500000 0.000000 0.23779(12) 0.0365(6) Uani 1 2 d S T P . .
O1 O 0.6139(6) -0.0986(6) -0.0855(3) 0.0279(12) Uani 1 1 d . . . . .
H1A H 0.625623 -0.185677 -0.081419 0.033 Uiso 1 1 d R . . . .
H1B H 0.602013 -0.079827 -0.125949 0.033 Uiso 1 1 d R . . . .
O2 O 0.3898(9) 0.6020(9) 0.2042(3) 0.060(2) Uani 1 1 d . U . . .
H2A H 0.392579 0.692475 0.206686 0.072 Uiso 1 1 d DR . . . .
H2B H 0.412219 0.561595 0.233326 0.072 Uiso 1 1 d DR . . . .
O3 O 0.5780(8) 0.0966(8) 0.1952(3) 0.0472(18) Uani 1 1 d . . . . .
O4 O 0.4079(8) 0.0791(10) 0.2811(3) 0.053(2) Uani 1 1 d . . . . .
O5 O 0.6198(5) 0.1789(5) 0.0086(3) 0.0180(10) Uani 1 1 d . U . . .
O6 O 0.6147(5) 0.3830(5) 0.0615(2) 0.0198(11) Uani 1 1 d . U . . .
N3 N 0.3673(6) 0.1089(6) 0.0567(3) 0.0145(11) Uani 1 1 d . U . . .
N4 N 0.3683(6) 0.3222(6) 0.1176(3) 0.0135(12) Uani 1 1 d . U . . .
C1 C 0.5637(7) 0.2666(7) 0.0459(3) 0.0130(12) Uani 1 1 d . U . . .
C2 C 0.2435(8) 0.0758(7) 0.0828(4) 0.0217(15) Uani 1 1 d . U . . .
H2 H 0.202552 -0.009236 0.072282 0.026 Uiso 1 1 calc R . . . .
C3 C 0.2427(8) 0.2890(8) 0.1423(4) 0.0213(15) Uani 1 1 d . U . . .
H3 H 0.200080 0.350094 0.171548 0.026 Uiso 1 1 calc R . . . .
C4 C 0.1746(9) 0.1665(8) 0.1256(4) 0.0249(16) Uani 1 1 d . U . . .
H4 H 0.086738 0.145643 0.142180 0.030 Uiso 1 1 calc R . . . .
C5 C 0.4223(7) 0.2299(7) 0.0748(3) 0.0126(13) Uani 1 1 d . U . . .
O10 O 0.8549(8) 0.1315(13) 0.2021(5) 0.089(4) Uani 1 1 d . . . . .
H10A H 0.911929 0.199518 0.200493 0.107 Uiso 1 1 d R . . . .
H10B H 0.807739 0.139108 0.237623 0.107 Uiso 1 1 d 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 2.079(6) 3_655 ?
Co1 O1 2.079(6) . ?
Co1 O5 2.108(5) . ?
Co1 O5 2.108(5) 3_655 ?
Co1 N3 2.159(6) 3_655 ?
Co1 N3 2.159(6) . ?
Co2 O2 2.065(7) 3_665 ?
Co2 O2 2.065(7) . ?
Co2 O6 2.119(5) . ?
Co2 O6 2.119(5) 3_665 ?
Co2 N4 2.142(6) . ?
Co2 N4 2.142(6) 3_665 ?
S1 O3 1.472(7) . ?
S1 O3 1.473(7) 3_655 ?
S1 O4 1.460(7) 3_655 ?
S1 O4 1.460(7) . ?
O1 H1A 0.8466 . ?
O1 H1B 0.8498 . ?
O2 H2A 0.8703 . ?
O2 H2B 0.7397 . ?
O5 C1 1.254(8) . ?
O6 C1 1.260(9) . ?
N3 C2 1.340(9) . ?
N3 C5 1.327(9) . ?
N4 C3 1.344(9) . ?
N4 C5 1.345(9) . ?
C1 C5 1.519(9) . ?
C2 H2 0.9300 . ?
C2 C4 1.396(11) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(10) . ?
C4 H4 0.9300 . ?
O10 H10A 0.8520 . ?
O10 H10B 0.8547 . ?

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 O1 88.1(3) 3_655 . ?
O1 Co1 O5 93.4(2) . 3_655 ?
O1 Co1 O5 93.4(2) 3_655 . ?
O1 Co1 O5 103.1(2) . . ?
O1 Co1 O5 103.1(2) 3_655 3_655 ?
O1 Co1 N3 86.3(2) . 3_655 ?
O1 Co1 N3 86.3(2) 3_655 . ?
O1 Co1 N3 174.3(2) 3_655 3_655 ?
O1 Co1 N3 174.3(2) . . ?
O5 Co1 O5 157.0(3) . 3_655 ?
O5 Co1 N3 86.8(2) . 3_655 ?
O5 Co1 N3 78.4(2) . . ?
O5 Co1 N3 78.4(2) 3_655 3_655 ?
O5 Co1 N3 86.8(2) 3_655 . ?
N3 Co1 N3 99.4(3) 3_655 . ?
O2 Co2 O2 88.4(5) 3_665 . ?
O2 Co2 O6 175.8(3) . . ?
O2 Co2 O6 87.9(3) 3_665 . ?
O2 Co2 O6 175.8(3) 3_665 3_665 ?
O2 Co2 O6 87.9(3) . 3_665 ?
O2 Co2 N4 91.1(2) 3_665 . ?
O2 Co2 N4 99.7(2) . . ?
O2 Co2 N4 99.7(2) 3_665 3_665 ?
O2 Co2 N4 91.1(2) . 3_665 ?
O6 Co2 O6 95.8(3) . 3_665 ?
O6 Co2 N4 91.6(2) . 3_665 ?
O6 Co2 N4 78.3(2) 3_665 3_665 ?
O6 Co2 N4 78.3(2) . . ?
O6 Co2 N4 91.6(2) 3_665 . ?
N4 Co2 N4 165.0(3) . 3_665 ?
O3 S1 O3 108.0(6) . 3_655 ?
O4 S1 O3 109.5(5) . . ?
O4 S1 O3 109.5(5) 3_655 3_655 ?
O4 S1 O3 112.0(5) . 3_655 ?
O4 S1 O3 112.0(5) 3_655 . ?
O4 S1 O4 105.9(6) 3_655 . ?
Co1 O1 H1A 116.6 . . ?
Co1 O1 H1B 121.9 . . ?
H1A O1 H1B 108.8 . . ?
Co2 O2 H2A 119.9 . . ?
Co2 O2 H2B 100.2 . . ?
H2A O2 H2B 117.8 . . ?
C1 O5 Co1 115.6(4) . . ?
C1 O6 Co2 115.8(4) . . ?
C2 N3 Co1 131.7(5) . . ?
C5 N3 Co1 111.6(5) . . ?
C5 N3 C2 116.8(6) . . ?
C3 N4 Co2 132.0(5) . . ?
C3 N4 C5 115.6(6) . . ?
C5 N4 Co2 112.4(5) . . ?
O5 C1 O6 125.4(6) . . ?
O5 C1 C5 117.5(6) . . ?
O6 C1 C5 117.1(6) . . ?
N3 C2 H2 119.4 . . ?
N3 C2 C4 121.2(7) . . ?
C4 C2 H2 119.4 . . ?
N4 C3 H3 118.9 . . ?
N4 C3 C4 122.1(7) . . ?
C4 C3 H3 118.9 . . ?
C2 C4 H4 121.4 . . ?
C3 C4 C2 117.3(7) . . ?
C3 C4 H4 121.4 . . ?
N3 C5 N4 127.0(6) . . ?
N3 C5 C1 116.8(6) . . ?
N4 C5 C1 116.2(6) . . ?
H10A O10 H10B 107.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1A O6 0.85 1.96 2.793(8) 168.1 4_645 yes
O1 H1B O4 0.85 1.91 2.734(9) 164.2 8_544 yes
O2 H2A O3 0.87 2.06 2.914(11) 168.4 3_665 yes
O2 H2B O2 0.74 2.53 2.88(2) 110.8 3_665 yes
O2 H2B O10 0.74 2.34 2.959(13) 142.8 5_455 yes
C3 H3 S1 0.93 3.02 3.932(8) 165.6 5_455 yes
C3 H3 O4 0.93 2.61 3.502(11) 160.1 7 yes
C4 H4 O10 0.93 2.54 3.456(12) 168.4 1_455 yes
O10 H10A O4 0.85 2.16 2.843(15) 137.3 5 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Co1 O5 C1 O6 -176.1(5) . . . . ?
Co1 O5 C1 C5 3.7(7) . . . . ?
Co1 N3 C2 C4 -178.1(6) . . . . ?
Co1 N3 C5 N4 -178.8(5) . . . . ?
Co1 N3 C5 C1 -1.1(6) . . . . ?
Co2 O6 C1 O5 -175.5(5) . . . . ?
Co2 O6 C1 C5 4.7(7) . . . . ?
Co2 N4 C3 C4 179.1(6) . . . . ?
Co2 N4 C5 N3 178.8(5) . . . . ?
Co2 N4 C5 C1 1.1(6) . . . . ?
O5 C1 C5 N3 -1.7(8) . . . . ?
O5 C1 C5 N4 176.2(6) . . . . ?
O6 C1 C5 N3 178.1(6) . . . . ?
O6 C1 C5 N4 -4.0(8) . . . . ?
N3 C2 C4 C3 -3.0(13) . . . . ?
N4 C3 C4 C2 1.6(12) . . . . ?
C2 N3 C5 N4 1.5(10) . . . . ?
C2 N3 C5 C1 179.1(6) . . . . ?
C3 N4 C5 N3 -2.8(10) . . . . ?
C3 N4 C5 C1 179.5(5) . . . . ?
C5 N3 C2 C4 1.6(11) . . . . ?
C5 N4 C3 C4 1.1(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.80(5)
2 0.20(5)

