# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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. 
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data_230608ych_0ma
_database_code_depnum_ccdc_archive 'CCDC 2330507'
loop_
_audit_author_name
_audit_author_address
'Chunhao Yuan'
;Shandong First Medical University
China
;
_audit_update_record             
;
2024-02-02 deposited with the CCDC.	2024-03-25 downloaded from the CCDC.
;
_audit_creation_date             2023-06-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H15 Cl O5'
_chemical_formula_sum            'C17 H15 Cl O5'
_chemical_formula_weight         334.74
_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'
Cl Cl 0.1484 0.1585 '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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.4419(16)
_cell_length_b                   7.0128(6)
_cell_length_c                   12.0067(11)
_cell_angle_alpha                90
_cell_angle_beta                 93.703(2)
_cell_angle_gamma                90
_cell_volume                     1549.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2869
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.23
_cell_measurement_theta_min      3.11
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.948
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7023
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0524 before and 0.0339 after correction.
The Ratio of minimum to maximum transmission is 0.9419.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8964
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.434
_diffrn_reflns_theta_min         1.106
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_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                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2536
_reflns_number_total             3460
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3460
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0492P)²+0.4599P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1096
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C009(H009)
2.b Secondary CH2 refined with riding coordinates:
 C00C(H00B,H00C), C00H(H00D,H00F)
2.c Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00E(H00E), C00G(H00G), C00I(H00I), C00J(H00J), C00L(H00L),
 C00M(H00M)
2.d Idealised Me refined as rotating group:
 C00N(H00H,H00K,H00N)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Cl01 Cl 1.02527(3) 0.58782(9) 0.31453(6) 0.0693(2) Uani 1 1 d . . . . .
O002 O 0.74739(6) 0.30842(17) 0.12040(9) 0.0372(3) Uani 1 1 d . . . . .
O003 O 0.81846(6) 0.17644(18) 0.26824(9) 0.0387(3) Uani 1 1 d . . . . .
O004 O 0.54062(6) 0.2261(2) 0.07337(11) 0.0489(3) Uani 1 1 d . . . . .
O005 O 0.66239(7) 0.52491(19) 0.09766(12) 0.0520(4) Uani 1 1 d . . . . .
O006 O 0.51211(7) 0.3802(3) 0.22759(13) 0.0674(5) Uani 1 1 d . . . . .
C007 C 0.68140(8) 0.3751(2) 0.13841(13) 0.0335(4) Uani 1 1 d . . . . .
C008 C 0.63432(8) 0.2597(2) 0.21367(13) 0.0329(4) Uani 1 1 d . . . . .
C009 C 0.77564(9) 0.1322(2) 0.17227(14) 0.0358(4) Uani 1 1 d . . . . .
H009 H 0.807839 0.074520 0.119869 0.043 Uiso 1 1 calc R U . . .
C00A C 0.65065(9) 0.0500(3) 0.20706(14) 0.0379(4) Uani 1 1 d . . . . .
H00A H 0.614108 -0.038905 0.216274 0.046 Uiso 1 1 calc R U . . .
C00B C 0.72964(9) 0.3791(3) 0.36261(13) 0.0349(4) Uani 1 1 d . . . . .
C00C C 0.78208(9) 0.2137(3) 0.36917(13) 0.0372(4) Uani 1 1 d . . . . .
H00B H 0.818645 0.237880 0.429244 0.045 Uiso 1 1 calc R U . . .
H00C H 0.755799 0.099812 0.388428 0.045 Uiso 1 1 calc R U . . .
C00D C 0.82339(9) 0.6324(2) 0.41478(14) 0.0377(4) Uani 1 1 d . . . . .
C00E C 0.74994(9) 0.5581(3) 0.38613(14) 0.0386(4) Uani 1 1 d . . . . .
H00E H 0.712713 0.647710 0.384144 0.046 Uiso 1 1 calc R U . . .
C00F C 0.55489(9) 0.2982(3) 0.17478(16) 0.0398(4) Uani 1 1 d . . . . .
C00G C 0.71667(9) -0.0076(3) 0.18824(14) 0.0394(4) Uani 1 1 d . . . . .
H00G H 0.726540 -0.137447 0.184898 0.047 Uiso 1 1 calc R U . . .
C00H C 0.65023(9) 0.3360(3) 0.33436(14) 0.0406(4) Uani 1 1 d . . . . .
H00D H 0.622196 0.451320 0.343554 0.049 Uiso 1 1 calc R U . . .
H00F H 0.634105 0.242137 0.386722 0.049 Uiso 1 1 calc R U . . .
C00I C 0.88370(9) 0.5745(3) 0.35840(15) 0.0419(4) Uani 1 1 d . . . . .
H00I H 0.878521 0.485776 0.300846 0.050 Uiso 1 1 calc R U . . .
C00J C 0.83311(11) 0.7686(2) 0.49919(16) 0.0464(4) Uani 1 1 d . . . . .
H00J H 0.793091 0.813677 0.534503 0.056 Uiso 1 1 calc R U . . .
C00K C 0.95114(10) 0.6509(3) 0.38944(17) 0.0477(5) Uani 1 1 d . . . . .
C00L C 0.96096(12) 0.7763(3) 0.4762(2) 0.0586(6) Uani 1 1 d . . . . .
H00L H 1.007213 0.820329 0.498450 0.070 Uiso 1 1 calc R U . . .
C00M C 0.90130(13) 0.8367(3) 0.53062(19) 0.0594(6) Uani 1 1 d . . . . .
H00M H 0.907293 0.923968 0.588806 0.071 Uiso 1 1 calc R U . . .
C00N C 0.46818(11) 0.2528(3) 0.0226(2) 0.0627(6) Uani 1 1 d . . . . .
H00H H 0.468889 0.237503 -0.056819 0.094 Uiso 1 1 calc R U . . .
H00K H 0.451415 0.378655 0.039087 0.094 Uiso 1 1 calc R U . . .
H00N H 0.436109 0.160071 0.051634 0.094 Uiso 1 1 calc R U . . .


_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
Cl01 C00K 1.741(2) . ?
O002 C007 1.3345(19) . ?
O002 C009 1.464(2) . ?
O003 C009 1.389(2) . ?
O003 C00C 1.4463(19) . ?
O004 C00F 1.329(2) . ?
O004 C00N 1.444(2) . ?
O005 C007 1.201(2) . ?
O006 C00F 1.191(2) . ?
C007 C008 1.526(2) . ?
C008 C00A 1.504(2) . ?
C008 C00F 1.533(2) . ?
C008 C00H 1.555(2) . ?
C009 H009 0.9800 . ?
C009 C00G 1.486(2) . ?
C00A H00A 0.9300 . ?
C00A C00G 1.316(2) . ?
C00B C00C 1.509(2) . ?
C00B C00E 1.335(2) . ?
C00B C00H 1.512(2) . ?
C00C H00B 0.9700 . ?
C00C H00C 0.9700 . ?
C00D C00E 1.471(2) . ?
C00D C00I 1.399(2) . ?
C00D C00J 1.396(3) . ?
C00E H00E 0.9300 . ?
C00G H00G 0.9300 . ?
C00H H00D 0.9700 . ?
C00H H00F 0.9700 . ?
C00I H00I 0.9300 . ?
C00I C00K 1.383(3) . ?
C00J H00J 0.9300 . ?
C00J C00M 1.375(3) . ?
C00K C00L 1.367(3) . ?
C00L H00L 0.9300 . ?
C00L C00M 1.382(3) . ?
C00M H00M 0.9300 . ?
C00N H00H 0.9600 . ?
C00N H00K 0.9600 . ?
C00N H00N 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
C007 O002 C009 122.02(12) . . ?
C009 O003 C00C 117.76(12) . . ?
C00F O004 C00N 117.43(16) . . ?
O002 C007 C008 118.01(14) . . ?
O005 C007 O002 119.06(15) . . ?
O005 C007 C008 122.89(15) . . ?
C007 C008 C00F 107.17(13) . . ?
C007 C008 C00H 106.80(13) . . ?
C00A C008 C007 111.35(13) . . ?
C00A C008 C00F 110.30(14) . . ?
C00A C008 C00H 111.06(14) . . ?
C00F C008 C00H 110.02(13) . . ?
O002 C009 H009 106.8 . . ?
O002 C009 C00G 111.62(13) . . ?
O003 C009 O002 109.39(13) . . ?
O003 C009 H009 106.8 . . ?
O003 C009 C00G 114.94(14) . . ?
C00G C009 H009 106.8 . . ?
C008 C00A H00A 120.0 . . ?
C00G C00A C008 119.98(15) . . ?
C00G C00A H00A 120.0 . . ?
C00C C00B C00H 117.78(15) . . ?
C00E C00B C00C 122.79(15) . . ?
C00E C00B C00H 119.33(16) . . ?
O003 C00C C00B 115.19(13) . . ?
O003 C00C H00B 108.5 . . ?
O003 C00C H00C 108.5 . . ?
C00B C00C H00B 108.5 . . ?
C00B C00C H00C 108.5 . . ?
H00B C00C H00C 107.5 . . ?
C00I C00D C00E 122.19(16) . . ?
C00J C00D C00E 119.03(16) . . ?
C00J C00D C00I 118.75(17) . . ?
C00B C00E C00D 128.61(16) . . ?
C00B C00E H00E 115.7 . . ?
C00D C00E H00E 115.7 . . ?
O004 C00F C008 109.93(14) . . ?
O006 C00F O004 124.92(16) . . ?
O006 C00F C008 125.15(17) . . ?
C009 C00G H00G 119.6 . . ?
C00A C00G C009 120.83(16) . . ?
C00A C00G H00G 119.6 . . ?
C008 C00H H00D 108.9 . . ?
C008 C00H H00F 108.9 . . ?
C00B C00H C008 113.55(13) . . ?
C00B C00H H00D 108.9 . . ?
C00B C00H H00F 108.9 . . ?
H00D C00H H00F 107.7 . . ?
C00D C00I H00I 120.5 . . ?
C00K C00I C00D 119.09(18) . . ?
C00K C00I H00I 120.5 . . ?
C00D C00J H00J 119.7 . . ?
C00M C00J C00D 120.62(19) . . ?
C00M C00J H00J 119.7 . . ?
C00I C00K Cl01 118.99(16) . . ?
C00L C00K Cl01 119.18(15) . . ?
C00L C00K C00I 121.83(18) . . ?
C00K C00L H00L 120.4 . . ?
C00K C00L C00M 119.17(19) . . ?
C00M C00L H00L 120.4 . . ?
C00J C00M C00L 120.4(2) . . ?
C00J C00M H00M 119.8 . . ?
C00L C00M H00M 119.8 . . ?
O004 C00N H00H 109.5 . . ?
O004 C00N H00K 109.5 . . ?
O004 C00N H00N 109.5 . . ?
H00H C00N H00K 109.5 . . ?
H00H C00N H00N 109.5 . . ?
H00K C00N H00N 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
Cl01 C00K C00L C00M 175.46(17) . . . . ?
O002 C007 C008 C00A -30.3(2) . . . . ?
O002 C007 C008 C00F -150.98(14) . . . . ?
O002 C007 C008 C00H 91.14(17) . . . . ?
O002 C009 C00G C00A -31.2(2) . . . . ?
O003 C009 C00G C00A 94.1(2) . . . . ?
O005 C007 C008 C00A 151.86(16) . . . . ?
O005 C007 C008 C00F 31.1(2) . . . . ?
O005 C007 C008 C00H -86.74(19) . . . . ?
C007 O002 C009 O003 -96.23(16) . . . . ?
C007 O002 C009 C00G 32.1(2) . . . . ?
C007 C008 C00A C00G 31.4(2) . . . . ?
C007 C008 C00F O004 66.72(17) . . . . ?
C007 C008 C00F O006 -113.4(2) . . . . ?
C007 C008 C00H C00B -40.37(19) . . . . ?
C008 C00A C00G C009 -0.6(3) . . . . ?
C009 O002 C007 O005 176.65(15) . . . . ?
C009 O002 C007 C008 -1.3(2) . . . . ?
C009 O003 C00C C00B -60.2(2) . . . . ?
C00A C008 C00F O004 -54.66(18) . . . . ?
C00A C008 C00F O006 125.2(2) . . . . ?
C00A C008 C00H C00B 81.22(18) . . . . ?
C00C O003 C009 O002 81.57(16) . . . . ?
C00C O003 C009 C00G -44.9(2) . . . . ?
C00C C00B C00E C00D 4.0(3) . . . . ?
C00C C00B C00H C008 -66.7(2) . . . . ?
C00D C00I C00K Cl01 -176.77(13) . . . . ?
C00D C00I C00K C00L 2.4(3) . . . . ?
C00D C00J C00M C00L 2.3(3) . . . . ?
C00E C00B C00C O003 -88.32(19) . . . . ?
C00E C00B C00H C008 116.66(18) . . . . ?
C00E C00D C00I C00K 179.71(16) . . . . ?
C00E C00D C00J C00M 177.91(18) . . . . ?
C00F C008 C00A C00G 150.22(16) . . . . ?
C00F C008 C00H C00B -156.36(15) . . . . ?
C00H C008 C00A C00G -87.53(19) . . . . ?
C00H C008 C00F O004 -177.52(14) . . . . ?
C00H C008 C00F O006 2.3(3) . . . . ?
C00H C00B C00C O003 95.19(17) . . . . ?
C00H C00B C00E C00D -179.52(15) . . . . ?
C00I C00D C00E C00B 42.6(3) . . . . ?
C00I C00D C00J C00M -3.6(3) . . . . ?
C00I C00K C00L C00M -3.7(3) . . . . ?
C00J C00D C00E C00B -138.97(19) . . . . ?
C00J C00D C00I C00K 1.3(3) . . . . ?
C00K C00L C00M C00J 1.3(3) . . . . ?
C00N O004 C00F O006 1.4(3) . . . . ?
C00N O004 C00F C008 -178.80(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
