# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_210819d
_database_code_depnum_ccdc_archive 'CCDC 2264741'
loop_
_audit_author_name
_audit_author_address
'Jianguo Zhang'
;BIT
China
;
_audit_update_record             
;
2023-05-23 deposited with the CCDC.	2023-07-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H12 Cl2 N12 O12'
_chemical_formula_weight         539.20

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   10.4353(9)
_cell_length_b                   17.0537(16)
_cell_length_c                   10.9355(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.693(2)
_cell_angle_gamma                90.00
_cell_volume                     1942.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1369
_cell_measurement_theta_min      2.389
_cell_measurement_theta_max      28.288

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      1.844
_exptl_crystal_density_diffrn    1.844
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1096
_exptl_absorpt_coefficient_mu    0.429
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9079
_exptl_absorpt_correction_T_max  0.9665
_exptl_absorpt_process_details   sadabs

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9375
_diffrn_reflns_av_R_equivalents  0.1022
_diffrn_reflns_av_sigmaI/netI    0.1030
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3420
_reflns_number_gt                1863
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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 > 2sigma(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. 
;

_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)+(0.1719P)²+4.2937P] 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         3420
_refine_ls_number_parameters     316
_refine_ls_number_restraints     124
_refine_ls_R_factor_all          0.1884
_refine_ls_R_factor_gt           0.1143
_refine_ls_wR_factor_ref         0.3396
_refine_ls_wR_factor_gt          0.2997
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.001
_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
Cl1 Cl 0.7540(2) 0.48093(13) 0.0345(2) 0.0555(7) Uani 1 1 d DU . .
Cl2 Cl 0.2771(2) 0.19369(14) 0.0586(2) 0.0617(8) Uani 1 1 d DU . .
N1 N 0.8178(7) 0.3803(4) 0.4979(6) 0.0508(18) Uani 1 1 d . . .
H1 H 0.8053 0.4302 0.4945 0.061 Uiso 1 1 calc R . .
N2 N 0.7582(6) 0.3368(4) 0.5808(6) 0.0484(18) Uani 1 1 d . . .
H2 H 0.7759 0.2878 0.5890 0.058 Uiso 1 1 calc R . .
N3 N 0.8998(6) 0.2679(4) 0.4300(6) 0.0430(16) Uani 1 1 d . . .
N4 N 1.0388(7) 0.2699(4) 0.2713(6) 0.0501(18) Uani 1 1 d . . .
H4 H 1.0814 0.2428 0.2214 0.060 Uiso 1 1 calc R . .
N5 N 0.9765(7) 0.1561(4) 0.3561(7) 0.065(2) Uani 1 1 d . . .
H5A H 0.9343 0.1301 0.4076 0.078 Uiso 1 1 calc R . .
H5B H 1.0228 0.1317 0.3061 0.078 Uiso 1 1 calc R . .
N6 N 1.1196(8) 0.3773(5) 0.1864(7) 0.071(2) Uani 1 1 d . . .
H6A H 1.1636 0.3464 0.1433 0.085 Uiso 1 1 calc R . .
H6B H 1.1263 0.4273 0.1780 0.085 Uiso 1 1 calc R . .
N7 N 0.9675(8) 0.4724(4) 0.3427(7) 0.058(2) Uani 1 1 d . . .
N8 N 0.6508(7) 0.4456(4) 0.6286(6) 0.0477(18) Uani 1 1 d . . .
N9 N 0.5031(6) 0.4433(4) 0.7793(6) 0.0491(18) Uani 1 1 d . . .
H9 H 0.4490 0.4697 0.8190 0.059 Uiso 1 1 calc R . .
N10 N 0.5403(8) 0.5549(4) 0.6750(8) 0.074(3) Uani 1 1 d . . .
H10A H 0.5794 0.5808 0.6211 0.088 Uiso 1 1 calc R . .
H10B H 0.4845 0.5779 0.7171 0.088 Uiso 1 1 calc R . .
N11 N 0.4545(7) 0.3381(4) 0.8917(7) 0.062(2) Uani 1 1 d . . .
H11A H 0.4015 0.3672 0.9281 0.074 Uiso 1 1 calc R . .
H11B H 0.4635 0.2896 0.9117 0.074 Uiso 1 1 calc R . .
N12 N 0.6319(7) 0.2471(4) 0.7576(7) 0.0539(19) Uani 1 1 d . . .
O1 O 0.7589(10) 0.4690(7) -0.0926(7) 0.101(4) Uani 0.689(6) 1 d PDU A 1
O2 O 0.6335(8) 0.4555(5) 0.0715(10) 0.077(3) Uani 0.689(6) 1 d PDU A 1
O3 O 0.8513(10) 0.4350(7) 0.0891(11) 0.117(4) Uani 0.689(6) 1 d PDU A 1
O4 O 0.7700(11) 0.5597(5) 0.0611(13) 0.113(4) Uani 0.689(6) 1 d PDU A 1
O5 O 0.2311(11) 0.1699(7) 0.1710(9) 0.082(3) Uani 0.583(6) 1 d PDU B 1
O6 O 0.2573(15) 0.1327(6) -0.0281(11) 0.115(5) Uani 0.583(6) 1 d PDU B 1
O7 O 0.4066(9) 0.2091(11) 0.0702(14) 0.139(6) Uani 0.583(6) 1 d PDU B 1
O8 O 0.2097(14) 0.2591(7) 0.0138(12) 0.120(4) Uani 0.583(6) 1 d PDU B 1
O9 O 1.0456(8) 0.5077(4) 0.2841(6) 0.076(2) Uani 1 1 d . . .
O10 O 0.8927(8) 0.5073(4) 0.4045(7) 0.082(2) Uani 1 1 d . . .
O11 O 0.7079(7) 0.2124(4) 0.6948(6) 0.071(2) Uani 1 1 d . . .
O12 O 0.5789(7) 0.2123(4) 0.8391(6) 0.072(2) Uani 1 1 d . . .
O1' O 0.6908(18) 0.5425(10) -0.0281(16) 0.101(4) Uani 0.311(6) 1 d PD A 2
O2' O 0.7429(18) 0.4110(8) -0.0315(18) 0.077(3) Uani 0.311(6) 1 d PD A 2
O3' O 0.712(2) 0.4716(14) 0.1518(12) 0.117(4) Uani 0.311(6) 1 d PD A 2
O4' O 0.8867(10) 0.5000(12) 0.046(2) 0.113(4) Uani 0.311(6) 1 d PD A 2
O5' O 0.1540(10) 0.1832(10) 0.0946(15) 0.082(3) Uani 0.417(6) 1 d PD B 2
O6' O 0.3364(17) 0.2598(8) 0.1137(16) 0.115(5) Uani 0.417(6) 1 d PD B 2
O7' O 0.3546(15) 0.1277(8) 0.0761(18) 0.139(6) Uani 0.417(6) 1 d PD B 2
O8' O 0.2692(18) 0.2069(12) -0.0706(9) 0.120(4) Uani 0.417(6) 1 d PD B 2
C1 C 0.9704(5) 0.2312(3) 0.3537(5) 0.044(2) Uani 1 1 d G . .
C2 C 1.0433(5) 0.3487(3) 0.2640(4) 0.048(2) Uani 1 1 d G . .
C3 C 0.9690(4) 0.3899(2) 0.3428(4) 0.046(2) Uani 1 1 d G . .
C4 C 0.8944(3) 0.34714(19) 0.4226(3) 0.0417(19) Uani 1 1 d G . .
C5 C 0.5657(6) 0.4807(3) 0.6928(5) 0.050(2) Uani 1 1 d G . .
C6 C 0.5203(5) 0.3672(3) 0.8075(4) 0.046(2) Uani 1 1 d G . .
C7 C 0.6109(4) 0.3270(2) 0.7399(4) 0.044(2) Uani 1 1 d G . .
C8 C 0.6719(3) 0.36990(19) 0.6501(3) 0.0431(19) Uani 1 1 d G . .


_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
Cl1 O4 1.383(7) . ?
Cl1 O3 1.387(8) . ?
Cl1 O3' 1.393(10) . ?
Cl1 O1' 1.395(10) . ?
Cl1 O2' 1.395(9) . ?
Cl1 O1 1.408(7) . ?
Cl1 O2 1.415(7) . ?
Cl1 O4' 1.421(9) . ?
Cl2 O7 1.375(8) . ?
Cl2 O5' 1.380(9) . ?
Cl2 O8 1.391(8) . ?
Cl2 O7' 1.392(9) . ?
Cl2 O6' 1.403(9) . ?
Cl2 O5 1.408(8) . ?
Cl2 O6 1.414(8) . ?
Cl2 O8' 1.427(9) . ?
N1 C4 1.313(7) . ?
N1 N2 1.353(9) . ?
N1 H1 0.8600 . ?
N2 C8 1.338(7) . ?
N2 H2 0.8600 . ?
N3 C1 1.307(7) . ?
N3 C4 1.355(7) . ?
N4 C2 1.347(8) . ?
N4 C1 1.356(7) . ?
N4 H4 0.8600 . ?
N5 C1 1.284(8) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N6 C2 1.297(8) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N7 O10 1.220(9) . ?
N7 O9 1.226(9) . ?
N7 C3 1.406(8) . ?
N8 C5 1.311(7) . ?
N8 C8 1.328(7) . ?
N9 C5 1.344(7) . ?
N9 C6 1.344(8) . ?
N9 H9 0.8600 . ?
N10 C5 1.306(8) . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?
N11 C6 1.282(8) . ?
N11 H11A 0.8600 . ?
N11 H11B 0.8600 . ?
N12 O12 1.231(8) . ?
N12 O11 1.232(8) . ?
N12 C7 1.392(8) . ?
C2 C3 1.3872(12) . ?
C3 C4 1.4095(12) . ?
C6 C7 1.4142(12) . ?
C7 C8 1.4095(12) . ?

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 Cl1 O3 112.5(7) . . ?
O4 Cl1 O3' 87.6(11) . . ?
O3 Cl1 O3' 78.8(10) . . ?
O4 Cl1 O1' 54.5(9) . . ?
O3 Cl1 O1' 161.1(9) . . ?
O3' Cl1 O1' 111.7(9) . . ?
O4 Cl1 O2' 160.9(10) . . ?
O3 Cl1 O2' 76.9(10) . . ?
O3' Cl1 O2' 111.0(9) . . ?
O1' Cl1 O2' 111.7(9) . . ?
O4 Cl1 O1 109.7(7) . . ?
O3 Cl1 O1 105.8(6) . . ?
O3' Cl1 O1 157.8(11) . . ?
O1' Cl1 O1 70.8(9) . . ?
O2' Cl1 O1 51.2(9) . . ?
O4 Cl1 O2 109.6(5) . . ?
O3 Cl1 O2 110.1(6) . . ?
O3' Cl1 O2 50.2(10) . . ?
O1' Cl1 O2 88.3(9) . . ?
O2' Cl1 O2 80.8(8) . . ?
O1 Cl1 O2 109.2(6) . . ?
O4 Cl1 O4' 69.8(9) . . ?
O3 Cl1 O4' 53.7(10) . . ?
O3' Cl1 O4' 108.1(10) . . ?
O1' Cl1 O4' 107.3(9) . . ?
O2' Cl1 O4' 106.8(8) . . ?
O1 Cl1 O4' 91.3(11) . . ?
O2 Cl1 O4' 157.7(11) . . ?
O7 Cl2 O5' 157.9(10) . . ?
O7 Cl2 O8 110.5(8) . . ?
O5' Cl2 O8 75.2(9) . . ?
O7 Cl2 O7' 65.3(9) . . ?
O5' Cl2 O7' 113.6(9) . . ?
O8 Cl2 O7' 166.7(10) . . ?
O7 Cl2 O6' 53.3(9) . . ?
O5' Cl2 O6' 112.0(8) . . ?
O8 Cl2 O6' 72.9(10) . . ?
O7' Cl2 O6' 110.8(9) . . ?
O7 Cl2 O5 111.3(7) . . ?
O5' Cl2 O5 48.5(8) . . ?
O8 Cl2 O5 110.2(7) . . ?
O7' Cl2 O5 82.8(9) . . ?
O6' Cl2 O5 91.3(9) . . ?
O7 Cl2 O6 107.7(8) . . ?
O5' Cl2 O6 89.9(9) . . ?
O8 Cl2 O6 107.8(7) . . ?
O7' Cl2 O6 63.6(9) . . ?
O6' Cl2 O6 157.0(9) . . ?
O5 Cl2 O6 109.3(7) . . ?
O7 Cl2 O8' 93.2(10) . . ?
O5' Cl2 O8' 107.9(8) . . ?
O8 Cl2 O8' 62.0(9) . . ?
O7' Cl2 O8' 105.0(9) . . ?
O6' Cl2 O8' 107.1(9) . . ?
O5 Cl2 O8' 155.3(9) . . ?
O6 Cl2 O8' 57.0(9) . . ?
C4 N1 N2 120.6(6) . . ?
C4 N1 H1 119.7 . . ?
N2 N1 H1 119.7 . . ?
C8 N2 N1 120.2(6) . . ?
C8 N2 H2 119.9 . . ?
N1 N2 H2 119.9 . . ?
C1 N3 C4 117.5(5) . . ?
C2 N4 C1 123.1(6) . . ?
C2 N4 H4 118.5 . . ?
C1 N4 H4 118.5 . . ?
C1 N5 H5A 120.0 . . ?
C1 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C2 N6 H6A 120.0 . . ?
C2 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
O10 N7 O9 121.4(8) . . ?
O10 N7 C3 119.6(7) . . ?
O9 N7 C3 118.9(7) . . ?
C5 N8 C8 117.3(5) . . ?
C5 N9 C6 123.7(6) . . ?
C5 N9 H9 118.1 . . ?
C6 N9 H9 118.1 . . ?
C5 N10 H10A 120.0 . . ?
C5 N10 H10B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
C6 N11 H11A 120.0 . . ?
C6 N11 H11B 120.0 . . ?
H11A N11 H11B 120.0 . . ?
O12 N12 O11 120.5(7) . . ?
O12 N12 C7 119.9(6) . . ?
O11 N12 C7 119.6(6) . . ?
N5 C1 N3 119.6(5) . . ?
N5 C1 N4 118.1(5) . . ?
N3 C1 N4 122.3(5) . . ?
N6 C2 N4 116.1(6) . . ?
N6 C2 C3 127.4(4) . . ?
N4 C2 C3 116.5(3) . . ?
C2 C3 N7 120.9(3) . . ?
C2 C3 C4 118.3 . . ?
N7 C3 C4 120.8(3) . . ?
N1 C4 N3 114.7(4) . . ?
N1 C4 C3 123.2(3) . . ?
N3 C4 C3 122.1(3) . . ?
N10 C5 N8 120.0(5) . . ?
N10 C5 N9 117.5(5) . . ?
N8 C5 N9 122.5(5) . . ?
N11 C6 N9 117.9(6) . . ?
N11 C6 C7 126.5(4) . . ?
N9 C6 C7 115.6(3) . . ?
N12 C7 C8 122.1(3) . . ?
N12 C7 C6 120.4(3) . . ?
C8 C7 C6 117.4 . . ?
N8 C8 N2 114.8(5) . . ?
N8 C8 C7 123.4(3) . . ?
N2 C8 C7 121.8(3) . . ?

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
C4 N1 N2 C8 -174.3(6) . . . . ?
C4 N3 C1 N5 -178.8(6) . . . . ?
C4 N3 C1 N4 1.5(11) . . . . ?
C2 N4 C1 N5 -177.4(7) . . . . ?
C2 N4 C1 N3 2.3(12) . . . . ?
C1 N4 C2 N6 175.5(7) . . . . ?
C1 N4 C2 C3 -2.7(9) . . . . ?
N6 C2 C3 N7 1.8(7) . . . . ?
N4 C2 C3 N7 179.7(7) . . . . ?
N6 C2 C3 C4 -178.5(6) . . . . ?
N4 C2 C3 C4 -0.6(4) . . . . ?
O10 N7 C3 C2 173.3(7) . . . . ?
O9 N7 C3 C2 -9.6(10) . . . . ?
O10 N7 C3 C4 -6.5(10) . . . . ?
O9 N7 C3 C4 170.6(6) . . . . ?
N2 N1 C4 N3 4.5(9) . . . . ?
N2 N1 C4 C3 -173.5(5) . . . . ?
C1 N3 C4 N1 177.2(6) . . . . ?
C1 N3 C4 C3 -4.8(8) . . . . ?
C2 C3 C4 N1 -177.8(4) . . . . ?
N7 C3 C4 N1 1.9(6) . . . . ?
C2 C3 C4 N3 4.4(4) . . . . ?
N7 C3 C4 N3 -175.9(6) . . . . ?
C8 N8 C5 N10 -179.5(7) . . . . ?
C8 N8 C5 N9 1.5(12) . . . . ?
C6 N9 C5 N10 -179.7(7) . . . . ?
C6 N9 C5 N8 -0.7(12) . . . . ?
C5 N9 C6 N11 -179.8(7) . . . . ?
C5 N9 C6 C7 0.4(9) . . . . ?
O12 N12 C7 C8 178.3(6) . . . . ?
O11 N12 C7 C8 1.4(10) . . . . ?
O12 N12 C7 C6 -5.7(9) . . . . ?
O11 N12 C7 C6 177.5(6) . . . . ?
N11 C6 C7 N12 3.1(6) . . . . ?
N9 C6 C7 N12 -177.0(7) . . . . ?
N11 C6 C7 C8 179.3(6) . . . . ?
N9 C6 C7 C8 -0.8(4) . . . . ?
C5 N8 C8 N2 179.0(6) . . . . ?
C5 N8 C8 C7 -2.0(9) . . . . ?
N1 N2 C8 N8 0.9(9) . . . . ?
N1 N2 C8 C7 -178.0(5) . . . . ?
N12 C7 C8 N8 177.9(7) . . . . ?
C6 C7 C8 N8 1.7(5) . . . . ?
N12 C7 C8 N2 -3.3(6) . . . . ?
C6 C7 C8 N2 -179.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.813
_refine_diff_density_min         -0.735
_refine_diff_density_rms         0.109
####################################################################### 
# 
# 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_210828d
_database_code_depnum_ccdc_archive 'CCDC 2264743'
loop_
_audit_author_name
_audit_author_address
'Jianguo Zhang'
;BIT
China
;
_audit_update_record             
;
2023-05-23 deposited with the CCDC.	2023-07-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H16 Cl2 N12 O14'
_chemical_formula_weight         575.23

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   15.3440(13)
_cell_length_b                   5.2963(5)
_cell_length_c                   14.1981(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.175(5)
_cell_angle_gamma                90.00
_cell_volume                     1035.50(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1378
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      27.584

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      1.845
_exptl_crystal_density_diffrn    1.845
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             588
_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9179
_exptl_absorpt_correction_T_max  0.9877
_exptl_absorpt_process_details   sadabs

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4954
_diffrn_reflns_av_R_equivalents  0.1068
_diffrn_reflns_av_sigmaI/netI    0.0853
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         25.02
_reflns_number_total             1832
_reflns_number_gt                1244
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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 > 2sigma(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. 
;

_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)+(0.0896P)²+0.0686P] 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         1832
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1155
_refine_ls_R_factor_gt           0.0735
_refine_ls_wR_factor_ref         0.1841
_refine_ls_wR_factor_gt          0.1663
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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
Cl1 Cl 0.63200(8) 0.0668(2) 0.19178(9) 0.0398(4) Uani 1 1 d . . .
N1 N 0.8379(2) 0.0426(7) -0.0362(3) 0.0322(9) Uani 1 1 d . . .
N2 N 0.7419(3) 0.3101(7) 0.0128(3) 0.0380(10) Uani 1 1 d . . .
H2 H 0.6848 0.3453 0.0063 0.046 Uiso 1 1 calc R . .
N3 N 0.9997(2) 0.1058(6) 0.0279(3) 0.0313(9) Uani 1 1 d . . .
H3 H 1.0523 0.1885 0.0638 0.038 Uiso 1 1 calc R . .
N4 N 0.6747(3) -0.0180(8) -0.1023(3) 0.0443(10) Uani 1 1 d . . .
H4A H 0.6794 -0.1461 -0.1370 0.053 Uiso 1 1 calc R . .
H4B H 0.6190 0.0254 -0.1067 0.053 Uiso 1 1 calc R . .
N5 N 0.7988(3) 0.6343(7) 0.1291(3) 0.0423(10) Uani 1 1 d . . .
H5A H 0.7404 0.6565 0.1212 0.051 Uiso 1 1 calc R . .
H5B H 0.8448 0.7301 0.1710 0.051 Uiso 1 1 calc R . .
N6 N 0.9916(3) 0.5378(7) 0.1453(3) 0.0322(9) Uani 1 1 d . . .
O1 O 0.9829(2) 0.7326(6) 0.1896(2) 0.0443(9) Uani 1 1 d . . .
O2 O 1.0734(2) 0.4706(6) 0.1566(2) 0.0423(8) Uani 1 1 d . . .
O3 O 0.6634(3) 0.3112(7) 0.1828(3) 0.0711(12) Uani 1 1 d . . .
O4 O 0.7023(3) -0.0493(8) 0.2832(3) 0.0776(13) Uani 1 1 d . . .
O5 O 0.5432(3) 0.0845(9) 0.2002(3) 0.0800(14) Uani 1 1 d . . .
O6 O 0.6177(3) -0.0824(8) 0.1021(3) 0.0637(11) Uani 1 1 d . . .
O7 O 0.4488(2) 0.5716(7) 0.0665(3) 0.0599(11) Uani 1 1 d . . .
H7A H 0.4895 0.6915 0.0910 0.072 Uiso 1 1 d R . .
H7B H 0.4618 0.4917 0.0224 0.072 Uiso 0.50 1 d PR A 1
H7C H 0.4558 0.4723 0.1164 0.072 Uiso 0.50 1 d PR B 2
C1 C 0.7522(3) 0.1106(9) -0.0427(3) 0.0330(10) Uani 1 1 d . . .
C2 C 0.8175(3) 0.4549(8) 0.0776(3) 0.0325(10) Uani 1 1 d . . .
C3 C 0.9092(3) 0.3952(8) 0.0822(3) 0.0322(10) Uani 1 1 d . . .
C4 C 0.9152(3) 0.1796(8) 0.0248(3) 0.0274(9) 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
Cl1 O3 1.407(4) . ?
Cl1 O4 1.411(4) . ?
Cl1 O5 1.422(4) . ?
Cl1 O6 1.431(4) . ?
N1 C1 1.327(5) . ?
N1 C4 1.333(5) . ?
N2 C2 1.356(6) . ?
N2 C1 1.368(5) . ?
N2 H2 0.8600 . ?
N3 C4 1.335(5) . ?
N3 N3 1.375(6) 3_755 ?
N3 H3 0.8600 . ?
N4 C1 1.307(6) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N5 C2 1.307(5) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N6 O2 1.245(4) . ?
N6 O1 1.246(4) . ?
N6 C3 1.404(6) . ?
O7 H7A 0.8500 . ?
O7 H7B 0.8500 . ?
O7 H7C 0.8500 . ?
C2 C3 1.415(6) . ?
C3 C4 1.430(6) . ?

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
O3 Cl1 O4 109.3(3) . . ?
O3 Cl1 O5 109.0(3) . . ?
O4 Cl1 O5 108.9(3) . . ?
O3 Cl1 O6 110.6(2) . . ?
O4 Cl1 O6 109.4(3) . . ?
O5 Cl1 O6 109.6(2) . . ?
C1 N1 C4 117.9(4) . . ?
C2 N2 C1 123.1(4) . . ?
C2 N2 H2 118.5 . . ?
C1 N2 H2 118.5 . . ?
C4 N3 N3 118.2(4) . 3_755 ?
C4 N3 H3 120.9 . . ?
N3 N3 H3 120.9 3_755 . ?
C1 N4 H4A 120.0 . . ?
C1 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C2 N5 H5A 120.0 . . ?
C2 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
O2 N6 O1 119.9(4) . . ?
O2 N6 C3 120.1(4) . . ?
O1 N6 C3 120.0(4) . . ?
H7A O7 H7B 107.7 . . ?
H7A O7 H7C 108.8 . . ?
H7B O7 H7C 108.8 . . ?
N4 C1 N1 119.7(4) . . ?
N4 C1 N2 118.2(4) . . ?
N1 C1 N2 122.2(4) . . ?
N5 C2 N2 117.2(4) . . ?
N5 C2 C3 126.6(4) . . ?
N2 C2 C3 116.2(4) . . ?
N6 C3 C2 120.5(4) . . ?
N6 C3 C4 121.8(4) . . ?
C2 C3 C4 117.7(4) . . ?
N1 C4 N3 115.8(4) . . ?
N1 C4 C3 122.8(4) . . ?
N3 C4 C3 121.4(4) . . ?

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
C4 N1 C1 N4 179.5(4) . . . . ?
C4 N1 C1 N2 -1.8(6) . . . . ?
C2 N2 C1 N4 179.4(4) . . . . ?
C2 N2 C1 N1 0.7(6) . . . . ?
C1 N2 C2 N5 -177.6(4) . . . . ?
C1 N2 C2 C3 2.4(6) . . . . ?
O2 N6 C3 C2 173.5(4) . . . . ?
O1 N6 C3 C2 -7.0(6) . . . . ?
O2 N6 C3 C4 -3.5(6) . . . . ?
O1 N6 C3 C4 176.0(4) . . . . ?
N5 C2 C3 N6 -1.4(7) . . . . ?
N2 C2 C3 N6 178.6(4) . . . . ?
N5 C2 C3 C4 175.8(4) . . . . ?
N2 C2 C3 C4 -4.3(6) . . . . ?
C1 N1 C4 N3 -179.2(4) . . . . ?
C1 N1 C4 C3 -0.4(6) . . . . ?
N3 N3 C4 N1 -2.2(6) 3_755 . . . ?
N3 N3 C4 C3 178.9(4) 3_755 . . . ?
N6 C3 C4 N1 -179.5(4) . . . . ?
C2 C3 C4 N1 3.4(6) . . . . ?
N6 C3 C4 N3 -0.7(6) . . . . ?
C2 C3 C4 N3 -177.8(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.679
_refine_diff_density_rms         0.093
