# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2026

####################################################################### 
# 
# 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_fr1ac1695
_database_code_depnum_ccdc_archive 'CCDC 2497816'
loop_
_audit_author_name
_audit_author_address
'Antonio L. Llamas-Saiz'
;Universidade de Santiago de Compostela
Spain
;
_audit_update_record             
;
2025-10-24 deposited with the CCDC.	2026-02-23 downloaded from the CCDC.
;

_audit_creation_date             2024-04-04T10:21:40-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C8 H13 Cl O2'
_chemical_formula_sum            'C8 H13 Cl O2'
_chemical_formula_weight         176.63
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   5.80950(10)
_cell_length_b                   7.8048(2)
_cell_length_c                   19.3744(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     878.47(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9160
_cell_measurement_theta_min      4.56
_cell_measurement_theta_max      74.34
_cell_measurement_wavelength     1.54178

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS-2016/2'
_exptl_absorpt_correction_T_min  0.6291
_exptl_absorpt_correction_T_max  0.7955
_shelx_estimated_absorpt_T_min   0.644
_shelx_estimated_absorpt_T_max   0.846

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  'Incoatec multilayer mirror'
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON III-14'
_diffrn_measurement_method       'omega and phi'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_number            13087
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.564
_diffrn_reflns_theta_max         74.604
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     1
_reflns_Friedel_coverage         0.666
_reflns_number_total             1793
_reflns_number_gt                1741
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'APPEX5v2023.9-2 (BRUKER AXS, 2021-2023)'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2019/1
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0222P)²+0.4114P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1793
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.027
_refine_ls_wR_factor_ref         0.0656
_refine_ls_wR_factor_gt          0.0646
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 691 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.009(9)
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.04

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.4958(5) 0.2741(3) 0.64667(13) 0.0259(5) Uani 1 1 d . . . . .
H1A H 0.625683 0.198605 0.65969 0.031 Uiso 1 1 calc R U . . .
H1B H 0.384656 0.275289 0.685406 0.031 Uiso 1 1 calc R U . . .
C2 C 0.5849(4) 0.4549(3) 0.63424(14) 0.0257(5) Uani 1 1 d . . . . .
H2A H 0.705974 0.451756 0.598309 0.031 Uiso 1 1 calc R U . . .
H2B H 0.655069 0.499108 0.677258 0.031 Uiso 1 1 calc R U . . .
C3 C 0.3929(4) 0.5760(3) 0.61132(11) 0.0169(4) Uani 1 1 d . . . . .
H3 H 0.284889 0.593398 0.650894 0.02 Uiso 1 1 calc R U . . .
C4 C 0.2596(4) 0.4940(3) 0.55155(11) 0.0199(5) Uani 1 1 d . . . . .
H4A H 0.120068 0.562578 0.541743 0.024 Uiso 1 1 calc R U . . .
H4B H 0.356812 0.493939 0.509575 0.024 Uiso 1 1 calc R U . . .
C5 C 0.1901(4) 0.3108(3) 0.56898(13) 0.0231(5) Uani 1 1 d . . . . .
H5A H 0.081537 0.311994 0.608364 0.028 Uiso 1 1 calc R U . . .
H5B H 0.109878 0.259468 0.528913 0.028 Uiso 1 1 calc R U . . .
C6 C 0.4936(4) 0.7498(2) 0.59085(11) 0.0160(4) Uani 1 1 d . . . . .
H6 H 0.606(5) 0.731(3) 0.5523(13) 0.019 Uiso 1 1 d . U . . .
C7 C 0.6120(4) 0.8357(3) 0.65072(12) 0.0179(4) Uani 1 1 d . . . . .
H7 H 0.515(5) 0.861(3) 0.6884(13) 0.021 Uiso 1 1 d . U . . .
C8 C 0.8354(4) 0.8672(3) 0.65070(12) 0.0199(5) Uani 1 1 d . . . . .
H8 H 0.924021 0.833573 0.611788 0.024 Uiso 1 1 calc R U . . .
O1 O 0.3861(3) 0.20772(19) 0.58632(9) 0.0217(4) Uani 1 1 d . . . . .
O2 O 0.3095(3) 0.85529(19) 0.56568(8) 0.0188(4) Uani 1 1 d . . . . .
H2 H 0.347(5) 0.957(4) 0.5714(14) 0.028 Uiso 1 1 d . U . . .
Cl1 Cl 0.97363(9) 0.96824(7) 0.71938(3) 0.02672(16) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 O1 1.429(3) . ?
C1 C2 1.522(3) . ?
C1 H1A 0.99 . ?
C1 H1B 0.99 . ?
C2 C3 1.528(3) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 C6 1.529(3) . ?
C3 C4 1.533(3) . ?
C3 H3 1 . ?
C4 C5 1.524(3) . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C5 O1 1.434(3) . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?
C6 O2 1.436(2) . ?
C6 C7 1.506(3) . ?
C6 H6 1.00(3) . ?
C7 C8 1.321(3) . ?
C7 H7 0.94(3) . ?
C8 Cl1 1.743(2) . ?
C8 H8 0.95 . ?
O2 H2 0.83(3) . ?

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
O1 C1 C2 110.99(19) . . ?
O1 C1 H1A 109.4 . . ?
C2 C1 H1A 109.4 . . ?
O1 C1 H1B 109.4 . . ?
C2 C1 H1B 109.4 . . ?
H1A C1 H1B 108 . . ?
C1 C2 C3 111.81(19) . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
C2 C3 C6 110.16(19) . . ?
C2 C3 C4 109.25(17) . . ?
C6 C3 C4 111.58(18) . . ?
C2 C3 H3 108.6 . . ?
C6 C3 H3 108.6 . . ?
C4 C3 H3 108.6 . . ?
C5 C4 C3 111.01(18) . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108 . . ?
O1 C5 C4 111.58(19) . . ?
O1 C5 H5A 109.3 . . ?
C4 C5 H5A 109.3 . . ?
O1 C5 H5B 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 108 . . ?
O2 C6 C7 110.28(17) . . ?
O2 C6 C3 108.14(18) . . ?
C7 C6 C3 111.69(17) . . ?
O2 C6 H6 108.2(15) . . ?
C7 C6 H6 110.0(16) . . ?
C3 C6 H6 108.4(15) . . ?
C8 C7 C6 122.1(2) . . ?
C8 C7 H7 123.3(16) . . ?
C6 C7 H7 114.6(17) . . ?
C7 C8 Cl1 122.47(19) . . ?
C7 C8 H8 118.8 . . ?
Cl1 C8 H8 118.8 . . ?
C1 O1 C5 110.04(17) . . ?
C6 O2 H2 108(2) . . ?

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
O1 C1 C2 C3 57.0(3) . . . . ?
C1 C2 C3 C6 -173.04(19) . . . . ?
C1 C2 C3 C4 -50.1(3) . . . . ?
C2 C3 C4 C5 49.7(3) . . . . ?
C6 C3 C4 C5 171.78(19) . . . . ?
C3 C4 C5 O1 -56.8(3) . . . . ?
C2 C3 C6 O2 176.44(18) . . . . ?
C4 C3 C6 O2 54.9(2) . . . . ?
C2 C3 C6 C7 -62.0(2) . . . . ?
C4 C3 C6 C7 176.45(18) . . . . ?
O2 C6 C7 C8 -123.7(2) . . . . ?
C3 C6 C7 C8 116.0(2) . . . . ?
C6 C7 C8 Cl1 179.41(15) . . . . ?
C2 C1 O1 C5 -62.1(3) . . . . ?
C4 C5 O1 C1 62.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C5 H5B O1 0.99 2.6 3.492(3) 150.5 2_456 yes
C8 H8 O2 0.95 2.42 3.210(3) 140.9 1_655 yes
O2 H2 O1 0.83(3) 1.99(3) 2.815(2) 171(3) 1_565 yes



# END of CIF
