# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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 1948700'
loop_
_audit_author_name
_audit_author_address
'yu zheng'
;central south university
China
;
_audit_update_record             
;
2019-08-22 deposited with the CCDC.	2020-10-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2.50 H2 Cl0.33 O0.67'
_chemical_formula_weight         54.52

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'
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                   11.3742(4)
_cell_length_b                   18.0280(7)
_cell_length_c                   7.5166(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.736(2)
_cell_angle_gamma                90.00
_cell_volume                     1476.02(10)
_cell_formula_units_Z            24
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3386
_cell_measurement_theta_min      1.87
_cell_measurement_theta_max      27.73

_exptl_crystal_description       BAR
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.451
_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            12862
_diffrn_reflns_av_R_equivalents  0.0146
_diffrn_reflns_av_sigmaI/netI    0.0119
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         27.73
_reflns_number_total             3386
_reflns_number_gt                2894
_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)+(0.0728P)²+0.6017P] 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         3386
_refine_ls_number_parameters     198
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1359
_refine_ls_wR_factor_gt          0.1268
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.051
_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
Cl2 Cl 0.63406(6) 0.17057(3) 0.29545(8) 0.0663(2) Uani 1 1 d . . .
Cl1 Cl 0.91126(5) 0.41522(5) 0.32195(10) 0.0791(2) Uani 1 1 d . . .
O3 O 0.43981(12) 0.27499(7) 0.28066(19) 0.0457(3) Uani 1 1 d . . .
C16 C 0.32648(14) 0.39254(9) 0.2248(2) 0.0325(3) Uani 1 1 d . . .
O2 O 0.45458(13) 0.50125(8) 0.2625(3) 0.0625(4) Uani 1 1 d . . .
O1 O 0.22696(14) 0.42532(9) 0.45212(19) 0.0588(4) Uani 1 1 d . . .
C15 C 0.54638(16) 0.30969(10) 0.2889(2) 0.0389(4) Uani 1 1 d . . .
C14 C 0.55791(15) 0.38678(9) 0.2890(2) 0.0366(4) Uani 1 1 d . . .
C13 C 0.44849(15) 0.43443(9) 0.2618(2) 0.0377(4) Uani 1 1 d . . .
C12 C 0.67133(16) 0.41950(11) 0.3003(2) 0.0431(4) Uani 1 1 d . . .
H12A H 0.6791 0.4709 0.3009 0.052 Uiso 1 1 calc R . .
C11 C 0.23867(15) 0.43977(10) 0.3019(2) 0.0395(4) Uani 1 1 d . . .
O4 O 0.09362(15) 0.33631(11) 0.0735(2) 0.0704(5) Uani 1 1 d . . .
C9 C 0.76085(19) 0.29833(13) 0.3088(3) 0.0547(5) Uani 1 1 d . . .
H9A H 0.8290 0.2689 0.3145 0.066 Uiso 1 1 calc R . .
C8 C 0.27401(16) 0.37777(9) 0.0168(2) 0.0362(3) Uani 1 1 d . . .
C7 C 0.77094(17) 0.37507(13) 0.3105(3) 0.0500(5) Uani 1 1 d . . .
C6 C 0.14555(18) 0.34894(11) -0.0426(3) 0.0467(4) Uani 1 1 d . . .
C5 C 0.35405(17) 0.32068(10) 0.3377(3) 0.0422(4) Uani 1 1 d . . .
H5A H 0.3873 0.3327 0.4684 0.051 Uiso 1 1 calc R . .
H5B H 0.2783 0.2934 0.3224 0.051 Uiso 1 1 calc R . .
C4 C 0.64951(19) 0.26612(11) 0.2985(2) 0.0468(4) Uani 1 1 d . . .
C18 C 0.3368(2) 0.38801(13) -0.1049(3) 0.0544(5) Uani 1 1 d D . .
C2 C 0.1744(2) 0.50414(11) 0.1909(3) 0.0540(5) Uani 1 1 d . . .
H2A H 0.1240 0.5282 0.2564 0.081 Uiso 1 1 calc R . .
H2B H 0.1239 0.4870 0.0726 0.081 Uiso 1 1 calc R . .
H2C H 0.2340 0.5387 0.1723 0.081 Uiso 1 1 calc R . .
C1 C 0.0803(3) 0.33857(17) -0.2439(3) 0.0757(7) Uani 1 1 d . . .
H1A H -0.0010 0.3202 -0.2574 0.114 Uiso 1 1 calc R . .
H1B H 0.1246 0.3037 -0.2966 0.114 Uiso 1 1 calc R . .
H1C H 0.0753 0.3852 -0.3071 0.114 Uiso 1 1 calc R . .
H18B H 0.4172(17) 0.4088(13) -0.068(4) 0.070(7) Uiso 1 1 d D . .
H18A H 0.306(2) 0.3770(13) -0.233(2) 0.066(7) Uiso 1 1 d 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
Cl2 C4 1.731(2) . ?
Cl1 C7 1.732(2) . ?
O3 C15 1.349(2) . ?
O3 C5 1.434(2) . ?
C16 C8 1.528(2) . ?
C16 C5 1.531(2) . ?
C16 C13 1.533(2) . ?
C16 C11 1.546(2) . ?
O2 C13 1.207(2) . ?
O1 C11 1.203(2) . ?
C15 C14 1.396(2) . ?
C15 C4 1.396(2) . ?
C14 C12 1.399(2) . ?
C14 C13 1.477(2) . ?
C12 C7 1.371(3) . ?
C12 H12A 0.9300 . ?
C11 C2 1.492(3) . ?
O4 C6 1.208(3) . ?
C9 C4 1.375(3) . ?
C9 C7 1.388(3) . ?
C9 H9A 0.9300 . ?
C8 C18 1.325(3) . ?
C8 C6 1.493(3) . ?
C6 C1 1.493(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C18 H18B 0.954(17) . ?
C18 H18A 0.949(16) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

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
C15 O3 C5 113.55(14) . . ?
C8 C16 C5 112.17(14) . . ?
C8 C16 C13 109.73(13) . . ?
C5 C16 C13 106.63(13) . . ?
C8 C16 C11 112.03(13) . . ?
C5 C16 C11 108.03(13) . . ?
C13 C16 C11 108.03(13) . . ?
O3 C15 C14 122.99(15) . . ?
O3 C15 C4 118.15(17) . . ?
C14 C15 C4 118.85(17) . . ?
C15 C14 C12 120.32(16) . . ?
C15 C14 C13 120.24(15) . . ?
C12 C14 C13 119.26(16) . . ?
O2 C13 C14 122.34(16) . . ?
O2 C13 C16 122.71(16) . . ?
C14 C13 C16 114.91(14) . . ?
C7 C12 C14 119.32(19) . . ?
C7 C12 H12A 120.3 . . ?
C14 C12 H12A 120.3 . . ?
O1 C11 C2 121.62(17) . . ?
O1 C11 C16 119.37(16) . . ?
C2 C11 C16 118.96(15) . . ?
C4 C9 C7 119.59(17) . . ?
C4 C9 H9A 120.2 . . ?
C7 C9 H9A 120.2 . . ?
C18 C8 C6 121.18(17) . . ?
C18 C8 C16 123.56(17) . . ?
C6 C8 C16 115.26(14) . . ?
C12 C7 C9 121.13(18) . . ?
C12 C7 Cl1 119.55(18) . . ?
C9 C7 Cl1 119.31(15) . . ?
O4 C6 C1 120.3(2) . . ?
O4 C6 C8 119.34(17) . . ?
C1 C6 C8 120.30(19) . . ?
O3 C5 C16 111.63(14) . . ?
O3 C5 H5A 109.3 . . ?
C16 C5 H5A 109.3 . . ?
O3 C5 H5B 109.3 . . ?
C16 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C9 C4 C15 120.79(19) . . ?
C9 C4 Cl2 120.62(15) . . ?
C15 C4 Cl2 118.59(16) . . ?
C8 C18 H18B 121.0(17) . . ?
C8 C18 H18A 123.8(15) . . ?
H18B C18 H18A 115(2) . . ?
C11 C2 H2A 109.5 . . ?
C11 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C11 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C6 C1 H1A 109.5 . . ?
C6 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C6 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

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
C5 O3 C15 C14 -21.0(2) . . . . ?
C5 O3 C15 C4 158.73(15) . . . . ?
O3 C15 C14 C12 179.13(15) . . . . ?
C4 C15 C14 C12 -0.6(2) . . . . ?
O3 C15 C14 C13 -5.8(2) . . . . ?
C4 C15 C14 C13 174.41(15) . . . . ?
C15 C14 C13 O2 179.34(18) . . . . ?
C12 C14 C13 O2 -5.6(3) . . . . ?
C15 C14 C13 C16 -3.0(2) . . . . ?
C12 C14 C13 C16 172.06(15) . . . . ?
C8 C16 C13 O2 90.1(2) . . . . ?
C5 C16 C13 O2 -148.23(19) . . . . ?
C11 C16 C13 O2 -32.3(2) . . . . ?
C8 C16 C13 C14 -87.55(17) . . . . ?
C5 C16 C13 C14 34.15(19) . . . . ?
C11 C16 C13 C14 150.05(14) . . . . ?
C15 C14 C12 C7 0.3(3) . . . . ?
C13 C14 C12 C7 -174.78(16) . . . . ?
C8 C16 C11 O1 140.43(17) . . . . ?
C5 C16 C11 O1 16.4(2) . . . . ?
C13 C16 C11 O1 -98.59(19) . . . . ?
C8 C16 C11 C2 -42.0(2) . . . . ?
C5 C16 C11 C2 -166.08(16) . . . . ?
C13 C16 C11 C2 78.93(19) . . . . ?
C5 C16 C8 C18 -107.1(2) . . . . ?
C13 C16 C8 C18 11.2(2) . . . . ?
C11 C16 C8 C18 131.20(19) . . . . ?
C5 C16 C8 C6 71.67(18) . . . . ?
C13 C16 C8 C6 -170.01(14) . . . . ?
C11 C16 C8 C6 -50.02(19) . . . . ?
C14 C12 C7 C9 0.3(3) . . . . ?
C14 C12 C7 Cl1 179.28(14) . . . . ?
C4 C9 C7 C12 -0.7(3) . . . . ?
C4 C9 C7 Cl1 -179.59(15) . . . . ?
C18 C8 C6 O4 175.8(2) . . . . ?
C16 C8 C6 O4 -3.0(3) . . . . ?
C18 C8 C6 C1 -6.5(3) . . . . ?
C16 C8 C6 C1 174.69(18) . . . . ?
C15 O3 C5 C16 56.04(19) . . . . ?
C8 C16 C5 O3 58.75(19) . . . . ?
C13 C16 C5 O3 -61.38(18) . . . . ?
C11 C16 C5 O3 -177.29(14) . . . . ?
C7 C9 C4 C15 0.3(3) . . . . ?
C7 C9 C4 Cl2 179.82(14) . . . . ?
O3 C15 C4 C9 -179.46(16) . . . . ?
C14 C15 C4 C9 0.3(3) . . . . ?
O3 C15 C4 Cl2 1.0(2) . . . . ?
C14 C15 C4 Cl2 -179.20(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        27.73
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.063
