# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2025

####################################################################### 
# 
# 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_161102_zhouyb_1
_database_code_depnum_ccdc_archive 'CCDC 2182610'
_audit_update_record             
;
2022-06-28 deposited with the CCDC.	2024-12-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H10 Cl0.33 N2 O8'
_chemical_formula_weight         298.02

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           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.5878(8)
_cell_length_b                   13.936(3)
_cell_length_c                   16.303(3)
_cell_angle_alpha                111.653(19)
_cell_angle_beta                 95.183(16)
_cell_angle_gamma                99.427(16)
_cell_volume                     942.7(3)
_cell_formula_units_Z            3
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             461
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6851
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0690
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         29.59
_reflns_number_total             4371
_reflns_number_gt                1771
_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)+(0.2000P)²+0.0000P] 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         4371
_refine_ls_number_parameters     299
_refine_ls_number_restraints     396
_refine_ls_R_factor_all          0.2947
_refine_ls_R_factor_gt           0.2030
_refine_ls_wR_factor_ref         0.5710
_refine_ls_wR_factor_gt          0.5234
_refine_ls_goodness_of_fit_ref   1.729
_refine_ls_restrained_S_all      1.654
_refine_ls_shift/su_max          1.836
_refine_ls_shift/su_mean         0.215

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
N1 N 0.7355(12) 0.7225(5) 0.1155(4) 0.0738(17) Uani 1 1 d . . .
O2 O 0.5910(13) 0.9155(4) 0.0332(3) 0.0855(16) Uani 1 1 d . . .
C5 C 0.9534(13) 0.6972(6) -0.0691(4) 0.0638(18) Uani 1 1 d . . .
C10 C 0.8067(14) 0.7688(5) -0.0105(4) 0.0622(17) Uani 1 1 d . . .
C9 C 0.7345(16) 0.8509(6) -0.0307(5) 0.079(2) Uani 1 1 d . . .
C6 C 1.0147(15) 0.7140(6) -0.1470(4) 0.073(2) Uani 1 1 d . . .
C13 C 0.6715(16) 0.7499(6) 0.2051(4) 0.073(2) Uani 1 1 d . A .
C3 C 1.1718(17) 0.5434(6) -0.1139(5) 0.085(2) Uani 1 1 d . . .
C11 C 0.7162(14) 0.7822(5) 0.0740(4) 0.0659(19) Uani 1 1 d . . .
C16 C 0.5796(17) 0.7915(5) 0.3810(4) 0.077(2) Uani 1 1 d . . .
C4 C 1.0359(15) 0.6124(6) -0.0520(4) 0.074(2) Uani 1 1 d . . .
C1 C 1.1568(18) 0.6407(7) -0.2078(5) 0.088(2) Uani 1 1 d . . .
O1 O 0.4396(14) 0.9151(4) 0.1597(4) 0.1011(19) Uani 1 1 d . . .
C18 C 0.4567(16) 0.6826(6) 0.2227(4) 0.080(2) Uani 1 1 d . . .
C7 C 0.9332(17) 0.8001(7) -0.1624(5) 0.083(2) Uani 1 1 d . . .
C17 C 0.4092(19) 0.7031(6) 0.3080(5) 0.089(2) Uani 1 1 d . A .
C19 C 0.529(19) 0.813(5) 0.473(2) 0.101(3) Uani 0.564(7) 1 d PU A 1
C2 C 1.2393(18) 0.5586(8) -0.1908(5) 0.092(3) Uani 1 1 d . . .
C14 C 0.844(2) 0.8343(7) 0.2746(5) 0.105(3) Uani 1 1 d . . .
C12 C 0.5726(18) 0.8762(6) 0.0989(5) 0.080(2) Uani 1 1 d . . .
C8 C 0.7975(18) 0.8707(7) -0.1064(5) 0.084(2) Uani 1 1 d . . .
C15 C 0.799(2) 0.8557(7) 0.3615(5) 0.108(3) Uani 1 1 d . A .
C22 C 0.484(7) 0.8742(14) 0.6555(16) 0.104(3) Uani 0.564(7) 1 d PU A 1
C24 C 0.470(4) 0.7310(12) 0.5043(9) 0.105(3) Uani 0.564(7) 1 d PU A 1
C20 C 0.550(4) 0.9182(12) 0.5354(9) 0.105(3) Uani 0.564(7) 1 d PU A 1
C21 C 0.537(5) 0.9409(13) 0.6248(10) 0.108(3) Uani 0.564(7) 1 d PU A 1
C23 C 0.440(4) 0.7514(13) 0.5947(10) 0.106(3) Uani 0.564(7) 1 d PU A 1
C19A C 0.54(2) 0.813(7) 0.473(3) 0.103(3) Uani 0.436(7) 1 d PU A 2
C22A C 0.455(8) 0.8437(19) 0.651(2) 0.104(3) Uani 0.436(7) 1 d PU A 2
C24A C 0.787(6) 0.8586(15) 0.5459(12) 0.103(3) Uani 0.436(7) 1 d PU A 2
C20A C 0.255(6) 0.8042(16) 0.4950(13) 0.106(3) Uani 0.436(7) 1 d PU A 2
C21A C 0.221(6) 0.8263(15) 0.5853(13) 0.108(3) Uani 0.436(7) 1 d PU A 2
C23A C 0.746(6) 0.8762(16) 0.6293(12) 0.105(3) Uani 0.436(7) 1 d PU A 2


_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
N1 C11 1.259(9) . ?
N1 C13 1.439(9) . ?
O2 C12 1.374(9) . ?
O2 C9 1.399(9) . ?
C5 C4 1.410(10) . ?
C5 C10 1.412(10) . ?
C5 C6 1.418(9) . ?
C10 C9 1.381(10) . ?
C10 C11 1.431(9) . ?
C9 C8 1.404(10) . ?
C6 C7 1.412(12) . ?
C6 C1 1.427(12) . ?
C13 C14 1.357(10) . ?
C13 C18 1.371(9) . ?
C3 C4 1.388(10) . ?
C3 C2 1.399(11) . ?
C11 C12 1.501(12) . ?
C16 C15 1.374(11) . ?
C16 C17 1.407(10) . ?
C16 C19A 1.46(5) . ?
C16 C19 1.46(4) . ?
C1 C2 1.372(12) . ?
O1 C12 1.212(9) . ?
C18 C17 1.357(9) . ?
C7 C8 1.353(12) . ?
C19 C20 1.42(6) . ?
C19 C24 1.42(7) . ?
C14 C15 1.379(11) . ?
C22 C21 1.21(2) . ?
C22 C23 1.60(3) . ?
C24 C23 1.420(19) . ?
C20 C21 1.38(2) . ?
C19A C24A 1.45(9) . ?
C19A C20A 1.37(11) . ?
C22A C21A 1.37(4) . ?
C22A C23A 1.45(4) . ?
C24A C23A 1.33(3) . ?
C20A C21A 1.42(3) . ?

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
C11 N1 C13 121.9(6) . . ?
C12 O2 C9 106.8(6) . . ?
C4 C5 C10 122.2(6) . . ?
C4 C5 C6 120.9(7) . . ?
C10 C5 C6 116.9(7) . . ?
C9 C10 C5 119.4(6) . . ?
C9 C10 C11 106.0(6) . . ?
C5 C10 C11 134.5(6) . . ?
C10 C9 O2 113.1(6) . . ?
C10 C9 C8 125.0(8) . . ?
O2 C9 C8 121.9(8) . . ?
C7 C6 C5 120.0(7) . . ?
C7 C6 C1 122.6(7) . . ?
C5 C6 C1 117.4(8) . . ?
C14 C13 C18 118.9(6) . . ?
C14 C13 N1 121.2(6) . . ?
C18 C13 N1 119.4(6) . . ?
C4 C3 C2 121.5(8) . . ?
N1 C11 C10 126.5(7) . . ?
N1 C11 C12 127.4(7) . . ?
C10 C11 C12 105.9(6) . . ?
C15 C16 C17 116.3(7) . . ?
C15 C16 C19A 121(4) . . ?
C17 C16 C19A 122(4) . . ?
C15 C16 C19 122(3) . . ?
C17 C16 C19 122(3) . . ?
C19A C16 C19 1(8) . . ?
C3 C4 C5 119.0(7) . . ?
C2 C1 C6 121.7(8) . . ?
C17 C18 C13 120.3(6) . . ?
C8 C7 C6 124.1(7) . . ?
C18 C17 C16 122.0(7) . . ?
C20 C19 C24 117(3) . . ?
C20 C19 C16 122(5) . . ?
C24 C19 C16 121(4) . . ?
C1 C2 C3 119.4(9) . . ?
C13 C14 C15 121.4(7) . . ?
O1 C12 O2 119.5(8) . . ?
O1 C12 C11 132.3(7) . . ?
O2 C12 C11 108.1(7) . . ?
C7 C8 C9 114.7(8) . . ?
C16 C15 C14 121.1(7) . . ?
C21 C22 C23 121(2) . . ?
C23 C24 C19 122(2) . . ?
C19 C20 C21 122(3) . . ?
C22 C21 C20 123.8(17) . . ?
C24 C23 C22 113.4(14) . . ?
C24A C19A C16 121(7) . . ?
C24A C19A C20A 118(4) . . ?
C16 C19A C20A 121(7) . . ?
C21A C22A C23A 114(2) . . ?
C23A C24A C19A 120(4) . . ?
C21A C20A C19A 119(4) . . ?
C22A C21A C20A 123(3) . . ?
C24A C23A C22A 122(2) . . ?

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 C5 C10 C9 179.4(5) . . . . ?
C6 C5 C10 C9 -0.8(8) . . . . ?
C4 C5 C10 C11 2.8(10) . . . . ?
C6 C5 C10 C11 -177.3(6) . . . . ?
C5 C10 C9 O2 -179.9(5) . . . . ?
C11 C10 C9 O2 -2.4(7) . . . . ?
C5 C10 C9 C8 -0.5(10) . . . . ?
C11 C10 C9 C8 177.0(6) . . . . ?
C12 O2 C9 C10 1.2(8) . . . . ?
C12 O2 C9 C8 -178.2(6) . . . . ?
C4 C5 C6 C7 -179.3(6) . . . . ?
C10 C5 C6 C7 0.9(8) . . . . ?
C4 C5 C6 C1 1.2(9) . . . . ?
C10 C5 C6 C1 -178.6(6) . . . . ?
C11 N1 C13 C14 -65.1(10) . . . . ?
C11 N1 C13 C18 123.1(8) . . . . ?
C13 N1 C11 C10 172.3(6) . . . . ?
C13 N1 C11 C12 -13.0(10) . . . . ?
C9 C10 C11 N1 178.1(6) . . . . ?
C5 C10 C11 N1 -5.0(11) . . . . ?
C9 C10 C11 C12 2.5(6) . . . . ?
C5 C10 C11 C12 179.4(7) . . . . ?
C2 C3 C4 C5 2.6(10) . . . . ?
C10 C5 C4 C3 178.2(6) . . . . ?
C6 C5 C4 C3 -1.7(9) . . . . ?
C7 C6 C1 C2 178.8(7) . . . . ?
C5 C6 C1 C2 -1.8(10) . . . . ?
C14 C13 C18 C17 3.0(14) . . . . ?
N1 C13 C18 C17 175.0(8) . . . . ?
C5 C6 C7 C8 0.3(11) . . . . ?
C1 C6 C7 C8 179.8(7) . . . . ?
C13 C18 C17 C16 -1.4(14) . . . . ?
C15 C16 C17 C18 -0.4(14) . . . . ?
C19A C16 C17 C18 -178(5) . . . . ?
C19 C16 C17 C18 -180(4) . . . . ?
C15 C16 C19 C20 39(8) . . . . ?
C17 C16 C19 C20 -142(5) . . . . ?
C19A C16 C19 C20 110(100) . . . . ?
C15 C16 C19 C24 -139(5) . . . . ?
C17 C16 C19 C24 41(8) . . . . ?
C19A C16 C19 C24 -67(100) . . . . ?
C6 C1 C2 C3 2.7(11) . . . . ?
C4 C3 C2 C1 -3.1(11) . . . . ?
C18 C13 C14 C15 -2.7(15) . . . . ?
N1 C13 C14 C15 -174.5(9) . . . . ?
C9 O2 C12 O1 -175.5(6) . . . . ?
C9 O2 C12 C11 0.5(7) . . . . ?
N1 C11 C12 O1 -2.2(12) . . . . ?
C10 C11 C12 O1 173.3(8) . . . . ?
N1 C11 C12 O2 -177.5(6) . . . . ?
C10 C11 C12 O2 -1.9(7) . . . . ?
C6 C7 C8 C9 -1.5(11) . . . . ?
C10 C9 C8 C7 1.6(10) . . . . ?
O2 C9 C8 C7 -179.1(6) . . . . ?
C17 C16 C15 C14 0.8(15) . . . . ?
C19A C16 C15 C14 179(5) . . . . ?
C19 C16 C15 C14 -180(4) . . . . ?
C13 C14 C15 C16 0.8(17) . . . . ?
C20 C19 C24 C23 -1(8) . . . . ?
C16 C19 C24 C23 176(4) . . . . ?
C24 C19 C20 C21 5(8) . . . . ?
C16 C19 C20 C21 -172(4) . . . . ?
C23 C22 C21 C20 3(4) . . . . ?
C19 C20 C21 C22 -6(5) . . . . ?
C19 C24 C23 C22 -1(5) . . . . ?
C21 C22 C23 C24 0(4) . . . . ?
C15 C16 C19A C24A -33(10) . . . . ?
C17 C16 C19A C24A 144(5) . . . . ?
C19 C16 C19A C24A -143(100) . . . . ?
C15 C16 C19A C20A 137(5) . . . . ?
C17 C16 C19A C20A -45(9) . . . . ?
C19 C16 C19A C20A 28(100) . . . . ?
C16 C19A C24A C23A -179(5) . . . . ?
C20A C19A C24A C23A 10(9) . . . . ?
C24A C19A C20A C21A -9(9) . . . . ?
C16 C19A C20A C21A -179(5) . . . . ?
C23A C22A C21A C20A 22(3) . . . . ?
C19A C20A C21A C22A -8(5) . . . . ?
C19A C24A C23A C22A 5(6) . . . . ?
C21A C22A C23A C24A -20(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.822
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         2.120
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.150
