# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_zhangxiaoyan_0623-2_auto
_database_code_depnum_ccdc_archive 'CCDC 2092879'
loop_
_audit_author_name
_audit_author_address
zhangxy
;LanZhou University
China
;
_audit_update_record             
;
2021-06-28 deposited with the CCDC.	2021-10-01 downloaded from the CCDC.
;
_audit_creation_date             2021-06-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H11 Cl O2'
_chemical_formula_sum            'C13 H11 Cl O2'
_chemical_formula_weight         234.67
_chemical_absolute_configuration ad
_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 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_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                   6.90260(14)
_cell_length_b                   6.93126(15)
_cell_length_c                   23.3243(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1115.92(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5980
_cell_measurement_temperature    293.0(7)
_cell_measurement_theta_max      76.0770
_cell_measurement_theta_min      3.7720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.876
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8732
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.180
_diffrn_reflns_theta_min         3.790
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.0(7)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     33.00  66.00   0.50    0.30    --  104.25 -61.00  90.00   66
  2  ω     32.00  57.00   0.50    0.30    --  104.25 -61.00 -60.00   50
  3  ω     36.00  96.00   0.50    0.30    --  104.25 -77.00 -90.00  120
  4  ω     44.00  69.00   0.50    0.30    --  104.25 -61.00-150.00   50
  5  ω     64.00 171.00   0.50    0.30    --  104.25   7.00 -79.00  214
  6  ω    -16.00  18.00   0.50    0.10    --  -46.32  19.00-120.00   68
  7  ω    -24.00   8.00   0.50    0.10    --  -46.32  19.00 -30.00   64
  8  ω    -22.00  22.00   0.50    0.10    --  -46.32  19.00  60.00   88
  9  ω    -56.00 -30.00   0.50    0.30    -- -102.00  61.00 150.00   52
 10  ω    -64.00 -38.00   0.50    0.30    -- -102.00  61.00 120.00   52
 11  ω    -68.00 -43.00   0.50    0.30    -- -102.00  61.00   0.00   50
 12  ω   -114.00 -89.00   0.50    0.30    -- -102.00 -30.00-150.00   50
 13  ω   -117.00 -92.00   0.50    0.10    --  -46.32-138.00-123.00   50
 14  ω   -115.00 -71.00   0.50    0.30    -- -102.00-131.00  52.00   88
 15  ω   -156.00-120.00   0.50    0.30    -- -102.00-131.00  52.00   72
 16  ω   -174.00-136.00   0.50    0.30    -- -102.00 -30.00-150.00   76
 17  ω    -87.00 -49.00   0.50    0.30    -- -102.00 123.00  38.00   76
 18  ω     31.00  72.00   0.50    0.10    --   46.32-149.00 154.00   82
 19  ω     77.00 109.00   0.50    0.10    --   46.32-149.00 154.00   64
 20  ω     33.00  58.00   0.50    0.30    --  104.25 -94.00-120.00   50
 21  ω     76.00 106.00   0.50    0.30    --  104.25 -94.00-120.00   60
 22  ω   -120.00 -87.00   0.50    0.30    -- -102.00 138.00 -60.00   66
 23  ω    -35.00   7.00   0.50    0.10    --  -46.32  37.00 -30.00   84
 24  ω    -13.00  28.00   0.50    0.10    --  -46.32   7.00 -79.00   82
 25  ω   -100.00 -50.00   0.50    0.10    --  -46.32  -7.00 104.00  100
 26  ω    -19.00   7.00   0.50    0.10    --  -46.32  19.00 -60.00   52
 27  ω     58.00  97.00   0.50    0.30    --  104.25-125.00-120.00   78
 28  ω    149.00 176.00   0.50    0.30    --  104.25  45.00 150.00   54
 29  ω     97.00 123.00   0.50    0.30    --  104.25 125.00  90.00   52
 30  ω     73.00  99.00   0.50    0.30    --  104.25 -94.00 -90.00   52
 31  ω    100.00 125.00   0.50    0.30    --  104.25  45.00 150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0081287000
_diffrn_orient_matrix_UB_12      0.0208962000
_diffrn_orient_matrix_UB_13      0.0657141000
_diffrn_orient_matrix_UB_21      0.2229002000
_diffrn_orient_matrix_UB_22      0.0053192000
_diffrn_orient_matrix_UB_23      -0.0025746000
_diffrn_orient_matrix_UB_31      -0.0060850000
_diffrn_orient_matrix_UB_32      0.2212591000
_diffrn_orient_matrix_UB_33      -0.0061627000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.650
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.932
_reflns_number_gt                2080
_reflns_number_total             2262
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 763 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0335
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0481P)²+0.1060P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0884
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12)
;
_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
Cl1 Cl 0.32120(12) 0.26367(12) 0.59342(3) 0.0771(3) Uani 1 1 d . . . . .
O1 O 0.2855(4) 0.9859(2) 0.39496(9) 0.0729(6) Uani 1 1 d . . . . .
O2 O 0.6037(3) 0.7433(4) 0.31068(9) 0.0811(6) Uani 1 1 d . . . . .
C1 C 0.2954(3) 0.6981(3) 0.45243(9) 0.0416(4) Uani 1 1 d . . . . .
C13 C 0.4328(4) 0.7260(4) 0.30278(10) 0.0502(5) Uani 1 1 d . . . . .
C2 C 0.3298(5) 0.7460(5) 0.24628(10) 0.0707(7) Uani 1 1 d . . . . .
H2A H 0.404285 0.687316 0.215639 0.085 Uiso 1 1 calc R U . . .
H2B H 0.307768 0.880748 0.237100 0.085 Uiso 1 1 calc R U . . .
C3 C 0.1409(5) 0.6417(5) 0.25493(11) 0.0672(7) Uani 1 1 d . . . . .
H3A H 0.155723 0.504440 0.248111 0.081 Uiso 1 1 calc R U . . .
H3B H 0.041661 0.691796 0.229532 0.081 Uiso 1 1 calc R U . . .
C4 C 0.0909(4) 0.6811(4) 0.31695(11) 0.0579(6) Uani 1 1 d . . . . .
H4A H 0.001706 0.584701 0.331498 0.070 Uiso 1 1 calc R U . . .
H4B H 0.032406 0.807604 0.321150 0.070 Uiso 1 1 calc R U . . .
C5 C 0.2855(3) 0.6713(3) 0.34881(9) 0.0426(5) Uani 1 1 d . . . . .
C6 C 0.2902(3) 0.8117(3) 0.39958(9) 0.0455(5) Uani 1 1 d . . . . .
C7 C 0.3295(4) 0.4720(3) 0.37534(9) 0.0519(5) Uani 1 1 d . . . . .
H7A H 0.235600 0.376858 0.362822 0.062 Uiso 1 1 calc R U . . .
H7B H 0.458220 0.428537 0.364743 0.062 Uiso 1 1 calc R U . . .
C8 C 0.3156(3) 0.5046(3) 0.43913(8) 0.0421(4) Uani 1 1 d . . . . .
C9 C 0.2813(3) 0.7599(4) 0.50915(9) 0.0506(5) Uani 1 1 d . . . . .
H9 H 0.267397 0.890248 0.517683 0.061 Uiso 1 1 calc R U . . .
C10 C 0.2883(4) 0.6249(4) 0.55223(10) 0.0535(5) Uani 1 1 d . . . . .
H10 H 0.277264 0.662268 0.590388 0.064 Uiso 1 1 calc R U . . .
C11 C 0.3121(4) 0.4322(4) 0.53801(9) 0.0515(5) Uani 1 1 d . . . . .
C12 C 0.3263(4) 0.3679(3) 0.48237(10) 0.0524(5) Uani 1 1 d . . . . .
H12 H 0.342479 0.237602 0.474097 0.063 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
Cl1 C11 1.743(2) . ?
O1 C6 1.213(3) . ?
O2 C13 1.200(3) . ?
C1 C6 1.463(3) . ?
C1 C8 1.384(3) . ?
C1 C9 1.394(3) . ?
C13 C2 1.504(3) . ?
C13 C5 1.526(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.504(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.512(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.537(3) . ?
C5 C6 1.533(3) . ?
C5 C7 1.544(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.508(3) . ?
C8 C12 1.386(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.374(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(4) . ?
C11 C12 1.376(3) . ?
C12 H12 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
C8 C1 C6 109.60(18) . . ?
C8 C1 C9 121.2(2) . . ?
C9 C1 C6 129.2(2) . . ?
O2 C13 C2 126.2(2) . . ?
O2 C13 C5 124.9(2) . . ?
C2 C13 C5 108.9(2) . . ?
C13 C2 H2A 110.9 . . ?
C13 C2 H2B 110.9 . . ?
C13 C2 C3 104.3(2) . . ?
H2A C2 H2B 108.9 . . ?
C3 C2 H2A 110.9 . . ?
C3 C2 H2B 110.9 . . ?
C2 C3 H3A 111.0 . . ?
C2 C3 H3B 111.0 . . ?
C2 C3 C4 103.8(2) . . ?
H3A C3 H3B 109.0 . . ?
C4 C3 H3A 111.0 . . ?
C4 C3 H3B 111.0 . . ?
C3 C4 H4A 110.8 . . ?
C3 C4 H4B 110.8 . . ?
C3 C4 C5 104.8(2) . . ?
H4A C4 H4B 108.9 . . ?
C5 C4 H4A 110.8 . . ?
C5 C4 H4B 110.8 . . ?
C13 C5 C4 103.35(18) . . ?
C13 C5 C6 111.81(18) . . ?
C13 C5 C7 111.90(19) . . ?
C4 C5 C7 113.9(2) . . ?
C6 C5 C4 111.33(18) . . ?
C6 C5 C7 104.74(16) . . ?
O1 C6 C1 127.7(2) . . ?
O1 C6 C5 124.3(2) . . ?
C1 C6 C5 108.03(17) . . ?
C5 C7 H7A 110.9 . . ?
C5 C7 H7B 110.9 . . ?
H7A C7 H7B 108.9 . . ?
C8 C7 C5 104.42(17) . . ?
C8 C7 H7A 110.9 . . ?
C8 C7 H7B 110.9 . . ?
C1 C8 C7 111.87(18) . . ?
C1 C8 C12 120.33(19) . . ?
C12 C8 C7 127.77(19) . . ?
C1 C9 H9 120.6 . . ?
C10 C9 C1 118.8(2) . . ?
C10 C9 H9 120.6 . . ?
C9 C10 H10 120.5 . . ?
C9 C10 C11 119.0(2) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 Cl1 118.20(17) . . ?
C12 C11 Cl1 118.64(19) . . ?
C12 C11 C10 123.2(2) . . ?
C8 C12 H12 121.3 . . ?
C11 C12 C8 117.4(2) . . ?
C11 C12 H12 121.3 . . ?

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
Cl1 C11 C12 C8 179.0(2) . . . . ?
O2 C13 C2 C3 159.6(3) . . . . ?
O2 C13 C5 C4 176.8(3) . . . . ?
O2 C13 C5 C6 57.0(3) . . . . ?
O2 C13 C5 C7 -60.2(3) . . . . ?
C1 C8 C12 C11 1.3(4) . . . . ?
C1 C9 C10 C11 1.0(3) . . . . ?
C13 C2 C3 C4 34.7(3) . . . . ?
C13 C5 C6 O1 49.2(3) . . . . ?
C13 C5 C6 C1 -132.36(19) . . . . ?
C13 C5 C7 C8 132.4(2) . . . . ?
C2 C13 C5 C4 -5.5(2) . . . . ?
C2 C13 C5 C6 -125.3(2) . . . . ?
C2 C13 C5 C7 117.5(2) . . . . ?
C2 C3 C4 C5 -38.7(3) . . . . ?
C3 C4 C5 C13 26.9(2) . . . . ?
C3 C4 C5 C6 147.1(2) . . . . ?
C3 C4 C5 C7 -94.8(2) . . . . ?
C4 C5 C6 O1 -65.8(3) . . . . ?
C4 C5 C6 C1 112.6(2) . . . . ?
C4 C5 C7 C8 -110.8(2) . . . . ?
C5 C13 C2 C3 -18.1(3) . . . . ?
C5 C7 C8 C1 -7.9(3) . . . . ?
C5 C7 C8 C12 174.0(2) . . . . ?
C6 C1 C8 C7 1.1(3) . . . . ?
C6 C1 C8 C12 179.3(2) . . . . ?
C6 C1 C9 C10 179.4(2) . . . . ?
C6 C5 C7 C8 11.1(3) . . . . ?
C7 C5 C6 O1 170.6(3) . . . . ?
C7 C5 C6 C1 -11.0(2) . . . . ?
C7 C8 C12 C11 179.2(3) . . . . ?
C8 C1 C6 O1 -175.2(3) . . . . ?
C8 C1 C6 C5 6.4(2) . . . . ?
C8 C1 C9 C10 0.2(3) . . . . ?
C9 C1 C6 O1 5.5(4) . . . . ?
C9 C1 C6 C5 -172.9(2) . . . . ?
C9 C1 C8 C7 -179.6(2) . . . . ?
C9 C1 C8 C12 -1.3(4) . . . . ?
C9 C10 C11 Cl1 179.83(18) . . . . ?
C9 C10 C11 C12 -1.0(4) . . . . ?
C10 C11 C12 C8 -0.1(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.377
_oxdiff_exptl_absorpt_empirical_full_min 0.646
####################################################################### 
# 
# 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_zhangxy_0604
_database_code_depnum_ccdc_archive 'CCDC 2099870'
loop_
_audit_author_name
_audit_author_address
Zhxy-YL
;Lan Zhou University
China
;
_audit_update_record             
;
2021-07-28 deposited with the CCDC.	2021-10-01 downloaded from the CCDC.
;
_audit_creation_date             2020-06-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H11 Cl O2'
_chemical_formula_sum            'C13 H11 Cl O2'
_chemical_formula_weight         234.67
_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 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.6872(8)
_cell_length_b                   6.0620(3)
_cell_length_c                   14.0247(9)
_cell_angle_alpha                90
_cell_angle_beta                 105.577(7)
_cell_angle_gamma                90
_cell_volume                     1120.91(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1150
_cell_measurement_temperature    292.69(10)
_cell_measurement_theta_max      68.4680
_cell_measurement_theta_min      6.7020
_shelx_estimated_absorpt_T_max   0.894
_shelx_estimated_absorpt_T_min   0.763
_exptl_absorpt_coefficient_mu    2.863
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3650
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         4.007
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.69(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     49.00 142.00   1.00    1.00    --  108.00 -25.00   0.00   93
  2  ω     74.00 167.00   1.00    1.00    --  108.00  25.00  30.00   93
  3  ω     68.00 116.00   1.00    1.00    --  108.00-111.00 -30.00   48
  4  ω     77.00 108.00   1.00    1.00    --  108.00-111.00-180.00   31
  5  ω     41.00  66.00   1.00    1.00    --  108.00-111.00-180.00   25
  6  ω     41.00 138.00   1.00    1.00    --  108.00 -77.00   0.00   97
  7  ω     55.00 123.00   1.00    1.00    --   54.00  57.00  60.00   68
  8  ω     66.00 106.00   1.00    1.00    --  108.00 178.00 -90.00   40
  9  ω    138.00 163.00   1.00    1.00    --  108.00 111.00-180.00   25
 10  ω     28.00  95.00   1.00    1.00    --   54.00 -99.00  30.00   67
 11  ω    -21.00  51.00   1.00    1.00    --    0.00  57.00  30.00   72
 12  ω     29.00 124.00   1.00    1.00    --   54.00  77.00 150.00   95
 13  ω    -12.00  47.00   1.00    1.00    --    0.00  57.00 120.00   59
 14  ω    -18.00  23.00   1.00    1.00    --   54.00 -38.00  90.00   41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0441732000
_diffrn_orient_matrix_UB_12      0.0425527000
_diffrn_orient_matrix_UB_13      -0.1116023000
_diffrn_orient_matrix_UB_21      0.1081517000
_diffrn_orient_matrix_UB_22      0.0257227000
_diffrn_orient_matrix_UB_23      -0.0117448000
_diffrn_orient_matrix_UB_31      0.0036035000
_diffrn_orient_matrix_UB_32      -0.2492048000
_diffrn_orient_matrix_UB_33      -0.0202420000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1492
_reflns_number_total             1975
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1975
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0460
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0686P)²+0.1047P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1323
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Cl1 Cl 0.85949(5) 0.08855(13) 0.98568(5) 0.0811(3) Uani 1 1 d . . . . .
O1 O 0.34574(15) -0.4816(4) 1.17047(17) 0.0920(7) Uani 1 1 d . . . . .
O2 O 0.47707(11) -0.2858(3) 1.16653(13) 0.0615(5) Uani 1 1 d . . . . .
C1 C 0.53754(15) -0.0981(3) 1.18255(17) 0.0479(5) Uani 1 1 d . . . . .
C2 C 0.60691(15) -0.0781(3) 1.12072(16) 0.0469(5) Uani 1 1 d . . . . .
C3 C 0.66393(16) 0.1135(3) 1.14935(16) 0.0492(5) Uani 1 1 d . . . . .
C4 C 0.62872(18) 0.2204(4) 1.23163(19) 0.0608(6) Uani 1 1 d . . . . .
H4A H 0.684334 0.234926 1.291047 0.073 Uiso 1 1 calc R U . . .
H4B H 0.600272 0.365272 1.211963 0.073 Uiso 1 1 calc R U . . .
C5 C 0.54922(17) 0.0657(4) 1.24827(17) 0.0531(6) Uani 1 1 d . . . . .
C6 C 0.4991(2) 0.1102(4) 1.3292(2) 0.0703(7) Uani 1 1 d . . . . .
H6A H 0.464540 0.251235 1.316605 0.084 Uiso 1 1 calc R U . . .
H6B H 0.551166 0.122245 1.391479 0.084 Uiso 1 1 calc R U . . .
C7 C 0.4236(2) -0.0641(4) 1.3397(2) 0.0698(7) Uani 1 1 d . . . . .
H7A H 0.385604 -0.010681 1.384310 0.084 Uiso 1 1 calc R U . . .
H7B H 0.459974 -0.195638 1.368805 0.084 Uiso 1 1 calc R U . . .
C8 C 0.35025(18) -0.1232(5) 1.2411(2) 0.0700(7) Uani 1 1 d . . . . .
H8A H 0.285480 -0.163925 1.251847 0.084 Uiso 1 1 calc R U . . .
H8B H 0.339462 0.005286 1.198360 0.084 Uiso 1 1 calc R U . . .
C9 C 0.38782(17) -0.3089(4) 1.19068(19) 0.0615(6) Uani 1 1 d . . . . .
C10 C 0.73995(16) 0.1709(4) 1.10735(17) 0.0562(6) Uani 1 1 d . . . . .
H10 H 0.777291 0.299477 1.125837 0.067 Uiso 1 1 calc R U . . .
C11 C 0.75936(18) 0.0306(4) 1.03624(18) 0.0564(6) Uani 1 1 d . . . . .
C12 C 0.70290(17) -0.1589(4) 1.00616(17) 0.0589(6) Uani 1 1 d . . . . .
H12 H 0.717073 -0.249227 0.957971 0.071 Uiso 1 1 calc R U . . .
C13 C 0.62534(17) -0.2132(4) 1.04801(17) 0.0554(6) Uani 1 1 d . . . . .
H13 H 0.586222 -0.338674 1.027560 0.067 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
Cl1 C11 1.740(2) . ?
O1 C9 1.192(3) . ?
O2 C1 1.389(2) . ?
O2 C9 1.360(3) . ?
C1 C2 1.453(3) . ?
C1 C5 1.335(3) . ?
C2 C3 1.397(3) . ?
C2 C13 1.383(3) . ?
C3 C4 1.511(3) . ?
C3 C10 1.371(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.502(3) . ?
C5 C6 1.500(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.513(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.518(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.493(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.390(3) . ?
C11 C12 1.385(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.384(3) . ?
C13 H13 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
C9 O2 C1 125.46(19) . . ?
O2 C1 C2 115.36(18) . . ?
C5 C1 O2 132.6(2) . . ?
C5 C1 C2 111.9(2) . . ?
C3 C2 C1 107.60(19) . . ?
C13 C2 C1 132.0(2) . . ?
C13 C2 C3 120.4(2) . . ?
C2 C3 C4 107.9(2) . . ?
C10 C3 C2 121.2(2) . . ?
C10 C3 C4 130.8(2) . . ?
C3 C4 H4A 110.9 . . ?
C3 C4 H4B 110.9 . . ?
H4A C4 H4B 109.0 . . ?
C5 C4 C3 104.11(18) . . ?
C5 C4 H4A 110.9 . . ?
C5 C4 H4B 110.9 . . ?
C1 C5 C4 108.3(2) . . ?
C1 C5 C6 131.5(2) . . ?
C6 C5 C4 120.2(2) . . ?
C5 C6 H6A 108.7 . . ?
C5 C6 H6B 108.7 . . ?
C5 C6 C7 114.3(2) . . ?
H6A C6 H6B 107.6 . . ?
C7 C6 H6A 108.7 . . ?
C7 C6 H6B 108.7 . . ?
C6 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
C6 C7 C8 112.2(2) . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C7 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 C7 112.5(2) . . ?
C9 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
O1 C9 O2 116.1(2) . . ?
O1 C9 C8 124.7(2) . . ?
O2 C9 C8 119.2(2) . . ?
C3 C10 H10 121.1 . . ?
C3 C10 C11 117.8(2) . . ?
C11 C10 H10 121.1 . . ?
C10 C11 Cl1 119.49(19) . . ?
C12 C11 Cl1 118.7(2) . . ?
C12 C11 C10 121.8(2) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.8(2) . . ?
C13 C12 H12 120.1 . . ?
C2 C13 C12 119.0(2) . . ?
C2 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?

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
Cl1 C11 C12 C13 177.53(18) . . . . ?
O2 C1 C2 C3 -177.64(17) . . . . ?
O2 C1 C2 C13 -0.6(4) . . . . ?
O2 C1 C5 C4 178.1(2) . . . . ?
O2 C1 C5 C6 -1.3(4) . . . . ?
C1 O2 C9 O1 179.3(2) . . . . ?
C1 O2 C9 C8 -1.7(4) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
C1 C2 C3 C10 176.7(2) . . . . ?
C1 C2 C13 C12 -175.0(2) . . . . ?
C1 C5 C6 C7 1.6(4) . . . . ?
C2 C1 C5 C4 2.3(3) . . . . ?
C2 C1 C5 C6 -177.1(2) . . . . ?
C2 C3 C4 C5 1.9(3) . . . . ?
C2 C3 C10 C11 -0.9(3) . . . . ?
C3 C2 C13 C12 1.8(3) . . . . ?
C3 C4 C5 C1 -2.6(3) . . . . ?
C3 C4 C5 C6 176.9(2) . . . . ?
C3 C10 C11 Cl1 -176.55(17) . . . . ?
C3 C10 C11 C12 1.6(4) . . . . ?
C4 C3 C10 C11 175.8(2) . . . . ?
C4 C5 C6 C7 -177.8(2) . . . . ?
C5 C1 C2 C3 -1.1(3) . . . . ?
C5 C1 C2 C13 176.0(2) . . . . ?
C5 C6 C7 C8 -48.2(3) . . . . ?
C6 C7 C8 C9 90.3(3) . . . . ?
C7 C8 C9 O1 118.8(3) . . . . ?
C7 C8 C9 O2 -60.1(3) . . . . ?
C9 O2 C1 C2 -158.3(2) . . . . ?
C9 O2 C1 C5 26.1(4) . . . . ?
C10 C3 C4 C5 -175.1(2) . . . . ?
C10 C11 C12 C13 -0.6(4) . . . . ?
C11 C12 C13 C2 -1.1(4) . . . . ?
C13 C2 C3 C4 -178.1(2) . . . . ?
C13 C2 C3 C10 -0.8(3) . . . . ?

_olex2_date_sample_data_collection 2020-06-04
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.400
_oxdiff_exptl_absorpt_empirical_full_min 0.680
