# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_ja
_database_code_depnum_ccdc_archive 'CCDC 1558121'
loop_
_audit_author_name
_audit_author_address
'Jun-An Xiao' 'Central Souty University'
_audit_update_record             
;
2018-02-07 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3.65 H3.30 Cl0.17 N0 O0.35'
_chemical_formula_weight         58.92

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   10.7240(10)
_cell_length_b                   10.8370(10)
_cell_length_c                   15.1156(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1756.7(3)
_cell_formula_units_Z            23
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3083
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      25.01

_exptl_crystal_description       cube
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            7524
_diffrn_reflns_av_R_equivalents  0.0674
_diffrn_reflns_av_sigmaI/netI    0.1034
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3083
_reflns_number_gt                1547
_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)+(0.0387P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3083
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1307
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1089
_refine_ls_wR_factor_gt          0.0893
_refine_ls_goodness_of_fit_ref   0.894
_refine_ls_restrained_S_all      0.894
_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 0.82643(9) 0.21416(11) 0.14747(8) 0.0825(4) Uani 1 1 d . . .
C21 C 0.5986(3) 0.2389(3) 0.3545(3) 0.0583(11) Uani 1 1 d . . .
H21A H 0.5923 0.2880 0.4047 0.070 Uiso 1 1 calc R . .
C20 C 0.5251(4) 0.0749(4) 0.2660(3) 0.0576(12) Uani 1 1 d . . .
H20A H 0.4674 0.0126 0.2552 0.069 Uiso 1 1 calc R . .
O2 O 0.3000(3) 0.0425(3) 0.5663(2) 0.0956(11) Uani 1 1 d . . .
C19 C 0.3468(4) -0.0424(4) 0.5257(3) 0.0639(12) Uani 1 1 d . . .
C18 C 0.3271(4) -0.1712(4) 0.5531(3) 0.0556(10) Uani 1 1 d . . .
C17 C 0.2856(4) 0.1500(4) 0.3804(3) 0.0584(12) Uani 1 1 d . . .
O1 O 0.3173(3) 0.3516(3) 0.4314(3) 0.1037(12) Uani 1 1 d . . .
C16 C 0.7030(3) 0.1898(4) 0.2206(3) 0.0571(11) Uani 1 1 d . . .
C15 C 0.4153(3) 0.1164(3) 0.4116(3) 0.0538(10) Uani 1 1 d . . .
H15A H 0.4336 0.1700 0.4622 0.065 Uiso 1 1 calc R . .
C14 C 0.2316(4) -0.1984(5) 0.6120(3) 0.0704(13) Uani 1 1 d . . .
H14A H 0.1819 -0.1349 0.6337 0.084 Uiso 1 1 calc R . .
C13 C 0.6924(3) 0.2623(4) 0.2939(3) 0.0618(11) Uani 1 1 d . . .
H13A H 0.7478 0.3270 0.3031 0.074 Uiso 1 1 calc R . .
C12 C 0.5140(3) 0.1439(4) 0.3420(3) 0.0507(10) Uani 1 1 d . . .
C11 C 0.2094(4) -0.3161(5) 0.6384(3) 0.0858(15) Uani 1 1 d . . .
H11A H 0.1447 -0.3321 0.6776 0.103 Uiso 1 1 calc R . .
C10 C 0.6192(4) 0.0948(4) 0.2050(3) 0.0601(11) Uani 1 1 d . . .
H10A H 0.6260 0.0458 0.1547 0.072 Uiso 1 1 calc R . .
C9 C 0.0302(5) 0.2087(7) 0.3589(4) 0.137(3) Uani 1 1 d . . .
H9A H 0.0118 0.1809 0.4185 0.164 Uiso 1 1 calc R . .
H9B H -0.0472 0.2363 0.3322 0.164 Uiso 1 1 calc R . .
C8 C 0.2809(6) -0.4113(5) 0.6080(4) 0.0897(17) Uani 1 1 d . . .
H8A H 0.2649 -0.4918 0.6262 0.108 Uiso 1 1 calc R . .
C7 C 0.4258(4) -0.0156(3) 0.4448(3) 0.0627(12) Uani 1 1 d . . .
H7A H 0.4011 -0.0712 0.3977 0.075 Uiso 1 1 calc R . .
H7B H 0.5123 -0.0326 0.4589 0.075 Uiso 1 1 calc R . .
C6 C 0.4005(4) -0.2675(4) 0.5233(3) 0.0652(12) Uani 1 1 d . . .
H6A H 0.4662 -0.2517 0.4847 0.078 Uiso 1 1 calc R . .
C5 C 0.3769(5) -0.3869(5) 0.5503(3) 0.0817(15) Uani 1 1 d . . .
H5A H 0.4262 -0.4511 0.5293 0.098 Uiso 1 1 calc R . .
C4 C 0.1197(5) 0.3145(5) 0.3629(4) 0.115(2) Uani 1 1 d . . .
H4A H 0.0857 0.3773 0.4018 0.138 Uiso 1 1 calc R . .
H4B H 0.1273 0.3502 0.3044 0.138 Uiso 1 1 calc R . .
C3 C 0.2485(4) 0.2791(5) 0.3957(3) 0.0737(13) Uani 1 1 d . . .
C2 C 0.0805(4) 0.1045(6) 0.3071(4) 0.1109(18) Uani 1 1 d . . .
H2A H 0.0830 0.1264 0.2449 0.133 Uiso 1 1 calc R . .
H2B H 0.0266 0.0332 0.3138 0.133 Uiso 1 1 calc R . .
C1 C 0.2096(4) 0.0733(5) 0.3387(3) 0.0846(14) Uani 1 1 d . . .
H1A H 0.2385 -0.0062 0.3280 0.102 Uiso 1 1 calc 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
Cl1 C16 1.745(4) . ?
C21 C13 1.384(5) . ?
C21 C12 1.385(5) . ?
C21 H21A 0.9300 . ?
C20 C12 1.377(5) . ?
C20 C10 1.383(5) . ?
C20 H20A 0.9300 . ?
O2 C19 1.215(4) . ?
C19 C18 1.471(5) . ?
C19 C7 1.515(5) . ?
C18 C6 1.383(5) . ?
C18 C14 1.388(5) . ?
C17 C1 1.324(5) . ?
C17 C3 1.473(6) . ?
C17 C15 1.513(5) . ?
O1 C3 1.206(5) . ?
C16 C13 1.362(5) . ?
C16 C10 1.387(5) . ?
C15 C7 1.520(4) . ?
C15 C12 1.522(5) . ?
C15 H15A 0.9800 . ?
C14 C11 1.357(6) . ?
C14 H14A 0.9300 . ?
C13 H13A 0.9300 . ?
C11 C8 1.365(6) . ?
C11 H11A 0.9300 . ?
C10 H10A 0.9300 . ?
C9 C2 1.476(7) . ?
C9 C4 1.496(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C8 C5 1.376(6) . ?
C8 H8A 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C6 C5 1.380(6) . ?
C6 H6A 0.9300 . ?
C5 H5A 0.9300 . ?
C4 C3 1.517(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C2 C1 1.503(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C1 H1A 0.9300 . ?

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
C13 C21 C12 121.5(4) . . ?
C13 C21 H21A 119.3 . . ?
C12 C21 H21A 119.3 . . ?
C12 C20 C10 122.3(4) . . ?
C12 C20 H20A 118.8 . . ?
C10 C20 H20A 118.8 . . ?
O2 C19 C18 121.1(4) . . ?
O2 C19 C7 119.5(4) . . ?
C18 C19 C7 119.3(4) . . ?
C6 C18 C14 117.9(4) . . ?
C6 C18 C19 122.8(4) . . ?
C14 C18 C19 119.2(4) . . ?
C1 C17 C3 120.3(4) . . ?
C1 C17 C15 124.3(4) . . ?
C3 C17 C15 115.3(4) . . ?
C13 C16 C10 120.8(4) . . ?
C13 C16 Cl1 119.4(3) . . ?
C10 C16 Cl1 119.7(4) . . ?
C17 C15 C7 113.4(3) . . ?
C17 C15 C12 112.2(3) . . ?
C7 C15 C12 111.2(3) . . ?
C17 C15 H15A 106.5 . . ?
C7 C15 H15A 106.5 . . ?
C12 C15 H15A 106.5 . . ?
C11 C14 C18 121.1(5) . . ?
C11 C14 H14A 119.4 . . ?
C18 C14 H14A 119.4 . . ?
C16 C13 C21 119.5(4) . . ?
C16 C13 H13A 120.2 . . ?
C21 C13 H13A 120.2 . . ?
C20 C12 C21 117.4(4) . . ?
C20 C12 C15 122.1(4) . . ?
C21 C12 C15 120.5(4) . . ?
C14 C11 C8 120.9(5) . . ?
C14 C11 H11A 119.5 . . ?
C8 C11 H11A 119.5 . . ?
C20 C10 C16 118.3(4) . . ?
C20 C10 H10A 120.8 . . ?
C16 C10 H10A 120.8 . . ?
C2 C9 C4 111.9(5) . . ?
C2 C9 H9A 109.2 . . ?
C4 C9 H9A 109.2 . . ?
C2 C9 H9B 109.2 . . ?
C4 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C11 C8 C5 119.2(5) . . ?
C11 C8 H8A 120.4 . . ?
C5 C8 H8A 120.4 . . ?
C19 C7 C15 113.9(3) . . ?
C19 C7 H7A 108.8 . . ?
C15 C7 H7A 108.8 . . ?
C19 C7 H7B 108.8 . . ?
C15 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C5 C6 C18 120.5(4) . . ?
C5 C6 H6A 119.8 . . ?
C18 C6 H6A 119.8 . . ?
C8 C5 C6 120.4(5) . . ?
C8 C5 H5A 119.8 . . ?
C6 C5 H5A 119.8 . . ?
C9 C4 C3 113.8(4) . . ?
C9 C4 H4A 108.8 . . ?
C3 C4 H4A 108.8 . . ?
C9 C4 H4B 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
O1 C3 C17 121.6(4) . . ?
O1 C3 C4 122.6(5) . . ?
C17 C3 C4 115.8(5) . . ?
C9 C2 C1 109.9(4) . . ?
C9 C2 H2A 109.7 . . ?
C1 C2 H2A 109.7 . . ?
C9 C2 H2B 109.7 . . ?
C1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C17 C1 C2 125.3(5) . . ?
C17 C1 H1A 117.4 . . ?
C2 C1 H1A 117.4 . . ?

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
O2 C19 C18 C6 -164.1(4) . . . . ?
C7 C19 C18 C6 16.6(6) . . . . ?
O2 C19 C18 C14 15.5(6) . . . . ?
C7 C19 C18 C14 -163.9(4) . . . . ?
C1 C17 C15 C7 -36.3(5) . . . . ?
C3 C17 C15 C7 146.6(4) . . . . ?
C1 C17 C15 C12 90.6(5) . . . . ?
C3 C17 C15 C12 -86.5(4) . . . . ?
C6 C18 C14 C11 -1.1(6) . . . . ?
C19 C18 C14 C11 179.3(4) . . . . ?
C10 C16 C13 C21 1.6(5) . . . . ?
Cl1 C16 C13 C21 -176.5(3) . . . . ?
C12 C21 C13 C16 -0.7(5) . . . . ?
C10 C20 C12 C21 2.3(5) . . . . ?
C10 C20 C12 C15 -176.1(3) . . . . ?
C13 C21 C12 C20 -1.2(5) . . . . ?
C13 C21 C12 C15 177.3(3) . . . . ?
C17 C15 C12 C20 -71.4(5) . . . . ?
C7 C15 C12 C20 56.7(5) . . . . ?
C17 C15 C12 C21 110.2(4) . . . . ?
C7 C15 C12 C21 -121.7(4) . . . . ?
C18 C14 C11 C8 0.3(6) . . . . ?
C12 C20 C10 C16 -1.5(5) . . . . ?
C13 C16 C10 C20 -0.6(5) . . . . ?
Cl1 C16 C10 C20 177.6(3) . . . . ?
C14 C11 C8 C5 0.3(7) . . . . ?
O2 C19 C7 C15 -12.3(6) . . . . ?
C18 C19 C7 C15 167.0(4) . . . . ?
C17 C15 C7 C19 -63.3(5) . . . . ?
C12 C15 C7 C19 169.3(3) . . . . ?
C14 C18 C6 C5 1.3(6) . . . . ?
C19 C18 C6 C5 -179.2(4) . . . . ?
C11 C8 C5 C6 -0.1(7) . . . . ?
C18 C6 C5 C8 -0.7(6) . . . . ?
C2 C9 C4 C3 -53.5(7) . . . . ?
C1 C17 C3 O1 -178.0(4) . . . . ?
C15 C17 C3 O1 -0.7(6) . . . . ?
C1 C17 C3 C4 1.5(6) . . . . ?
C15 C17 C3 C4 178.8(4) . . . . ?
C9 C4 C3 O1 -154.0(5) . . . . ?
C9 C4 C3 C17 26.5(7) . . . . ?
C4 C9 C2 C1 50.1(6) . . . . ?
C3 C17 C1 C2 -3.0(7) . . . . ?
C15 C17 C1 C2 -180.0(4) . . . . ?
C9 C2 C1 C17 -23.4(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.033
