# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 2190850'
loop_
_audit_author_name
_audit_author_address
'Miao Wang'
;Luoyang Normal University
China
;
_audit_update_record             
;
2022-07-17 deposited with the CCDC.	2023-07-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H7 Cl O'
_chemical_formula_weight         166.60

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   15.423(3)
_cell_length_b                   4.9337(9)
_cell_length_c                   11.308(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.313(2)
_cell_angle_gamma                90
_cell_volume                     806.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    8110
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      30.73

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.406
_shelx_estimated_absorpt_T_min   0.916
_shelx_estimated_absorpt_T_max   0.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16540
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.408
_diffrn_reflns_theta_max         32.035
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2632
_reflns_number_gt                2363
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0919P)²+0.8931P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2632
_refine_ls_number_parameters     125
_refine_ls_number_restraints     61
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0625
_refine_ls_wR_factor_ref         0.2021
_refine_ls_wR_factor_gt          0.1976
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.062
_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_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
C9A C 0.5750(8) -0.284(3) 0.4120(12) 0.065(2) Uani 0.562(11) 1 d D U P A 1
H9A1 H 0.5466 -0.3897 0.3360 0.078 Uiso 0.562(11) 1 calc R U P A 1
H9A2 H 0.6155 -0.4038 0.4754 0.078 Uiso 0.562(11) 1 calc R U P A 1
O1A O 0.5075(4) -0.1900(12) 0.4538(7) 0.0829(19) Uani 0.562(11) 1 d D U P A 1
H1A H 0.520(4) -0.16(2) 0.532(3) 0.099 Uiso 0.562(11) 1 d D U P A 1
C9B C 0.5578(10) -0.274(4) 0.3782(11) 0.054(2) Uani 0.438(11) 1 d D U P A 2
H9B1 H 0.4980 -0.2097 0.3227 0.065 Uiso 0.438(11) 1 calc R U P A 2
H9B2 H 0.5716 -0.4427 0.3447 0.065 Uiso 0.438(11) 1 calc R U P A 2
O1B O 0.5558(6) -0.3148(15) 0.5010(7) 0.072(2) Uani 0.438(11) 1 d D U P A 2
H1B H 0.609(2) -0.34(2) 0.557(3) 0.086 Uiso 0.438(11) 1 d D U P A 2
C1 C 0.86679(15) 0.6827(4) 0.3259(2) 0.0358(4) Uani 1 1 d . . . . .
C2 C 0.79583(18) 0.5901(5) 0.2214(2) 0.0441(5) Uani 1 1 d . . . . .
H2 H 0.7885 0.6562 0.1415 0.053 Uiso 1 1 calc R U . . .
C3 C 0.73554(18) 0.3966(6) 0.2376(2) 0.0452(5) Uani 1 1 d . . . . .
H3 H 0.6875 0.3329 0.1678 0.054 Uiso 1 1 calc R U . . .
C4 C 0.74600(15) 0.2961(5) 0.3573(2) 0.0369(4) Uani 1 1 d . . . . .
C5 C 0.81845(17) 0.3945(5) 0.4615(2) 0.0421(5) Uani 1 1 d . . . . .
H5 H 0.8262 0.3295 0.5418 0.051 Uiso 1 1 calc R U . . .
C6 C 0.87858(16) 0.5879(5) 0.4459(2) 0.0411(5) Uani 1 1 d . . . . .
H6 H 0.9265 0.6537 0.5153 0.049 Uiso 1 1 calc R U . . .
C7 C 0.68390(17) 0.0982(5) 0.3733(3) 0.0425(5) Uani 1 1 d . . . . .
C8 C 0.63060(19) -0.0679(5) 0.3851(3) 0.0503(6) Uani 1 1 d D U . . .
Cl1 Cl 0.94238(4) 0.92349(13) 0.30566(6) 0.0482(2) Uani 1 1 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
C9A O1A 1.366(12) . ?
C9A C8 1.465(16) . ?
C9A H9A1 0.9700 . ?
C9A H9A2 0.9700 . ?
O1A H1A 0.848(19) . ?
C9B O1B 1.415(13) . ?
C9B C8 1.495(19) . ?
C9B H9B1 0.9700 . ?
C9B H9B2 0.9700 . ?
O1B H1B 0.86(2) . ?
C1 C2 1.380(3) . ?
C1 C6 1.386(3) . ?
C1 Cl1 1.734(2) . ?
C2 C3 1.389(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.397(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.399(3) . ?
C4 C7 1.422(3) . ?
C5 C6 1.384(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.201(4) . ?

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
O1A C9A C8 113.3(11) . . ?
O1A C9A H9A1 108.9 . . ?
C8 C9A H9A1 108.9 . . ?
O1A C9A H9A2 108.9 . . ?
C8 C9A H9A2 108.9 . . ?
H9A1 C9A H9A2 107.7 . . ?
C9A O1A H1A 119(3) . . ?
O1B C9B C8 108.6(10) . . ?
O1B C9B H9B1 110.0 . . ?
C8 C9B H9B1 110.0 . . ?
O1B C9B H9B2 110.0 . . ?
C8 C9B H9B2 110.0 . . ?
H9B1 C9B H9B2 108.4 . . ?
C9B O1B H1B 114(3) . . ?
C2 C1 C6 121.4(2) . . ?
C2 C1 Cl1 118.91(18) . . ?
C6 C1 Cl1 119.64(17) . . ?
C1 C2 C3 118.9(2) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C2 C3 C4 121.0(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 118.8(2) . . ?
C5 C4 C7 120.5(2) . . ?
C3 C4 C7 120.7(2) . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 119.5(2) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C8 C7 C4 179.1(3) . . ?
C7 C8 C9A 173.0(6) . . ?
C7 C8 C9B 171.2(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
C6 C1 C2 C3 -0.4(4) . . . . ?
Cl1 C1 C2 C3 179.8(2) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C2 C3 C4 C7 179.9(3) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C7 C4 C5 C6 -179.7(2) . . . . ?
C4 C5 C6 C1 -0.3(4) . . . . ?
C2 C1 C6 C5 0.5(4) . . . . ?
Cl1 C1 C6 C5 -179.60(19) . . . . ?

_refine_diff_density_max         0.277
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.095

