# 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. 
# 
#######################################################################

data_mo_20231142_0m
_database_code_depnum_ccdc_archive 'CCDC 2333546'
loop_
_audit_author_name
_audit_author_address
'Ruowen Li'
;Shanghai University of Technology
China
;
_audit_update_record             
;
2024-02-18 deposited with the CCDC.	2024-05-19 downloaded from the CCDC.
;
_audit_creation_date             2023-07-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H11 Cl F2 O3'
_chemical_formula_sum            'C13 H11 Cl F2 O3'
_chemical_formula_weight         288.67
_chemical_melting_point          88.8
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'
F F 0.0171 0.0103 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3033(4)
_cell_length_b                   7.5694(4)
_cell_length_c                   12.9533(7)
_cell_angle_alpha                75.029(2)
_cell_angle_beta                 74.131(2)
_cell_angle_gamma                65.035(2)
_cell_volume                     615.99(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4678
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.403
_cell_measurement_theta_min      3.009
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.912
_exptl_absorpt_coefficient_mu    0.336
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1264 before and 0.0692 after correction.
The Ratio of minimum to maximum transmission is 0.7384.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yello
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7027
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.403
_diffrn_reflns_theta_min         3.009
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_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                2207
_reflns_number_total             2489
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2489
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0411
_refine_ls_restrained_S_all      1.055
_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)+(0.0510P)²+0.2244P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1124
_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:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C3(H3)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_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 0.29125(7) 0.35135(6) 0.34718(3) 0.03451(17) Uani 1 1 d . . . . .
F2 F 0.56109(16) 0.30494(15) 0.83493(8) 0.0336(3) Uani 1 1 d . . . . .
F1 F 0.78385(16) 0.01396(17) 0.88630(8) 0.0355(3) Uani 1 1 d . . . . .
O2 O 0.05831(17) 0.24509(17) 0.89517(9) 0.0255(3) Uani 1 1 d . . . . .
O1 O 0.95509(19) 0.0854(2) 0.68077(11) 0.0371(3) Uani 1 1 d . . . . .
O3 O -0.1720(2) 0.55485(19) 0.89307(11) 0.0395(4) Uani 1 1 d . . . . .
C5 C 0.3405(3) 0.2317(2) 0.55592(13) 0.0243(4) Uani 1 1 d . . . . .
H5 H 0.205078 0.233030 0.571451 0.029 Uiso 1 1 calc R U . . .
C1 C 0.6496(2) 0.1756(2) 0.61382(13) 0.0225(3) Uani 1 1 d . . . . .
C10 C 0.7728(3) 0.1200(2) 0.69889(14) 0.0246(4) Uani 1 1 d . . . . .
C4 C 0.4311(3) 0.2822(2) 0.44998(13) 0.0257(4) Uani 1 1 d . . . . .
C7 C 0.3451(2) 0.1242(2) 0.75537(12) 0.0215(3) Uani 1 1 d . . . . .
H7 H 0.285806 0.027834 0.753594 0.026 Uiso 1 1 calc R U . . .
C8 C 0.4936(2) 0.0235(2) 0.83631(13) 0.0232(4) Uani 1 1 d . . . . .
H8A H 0.413704 0.034886 0.911189 0.028 Uiso 1 1 calc R U . . .
H8B H 0.564198 -0.118761 0.830996 0.028 Uiso 1 1 calc R U . . .
C9 C 0.6516(3) 0.1121(3) 0.81588(13) 0.0246(4) Uani 1 1 d . . . . .
C12 C -0.1125(2) 0.3862(2) 0.93811(13) 0.0249(4) Uani 1 1 d . . . . .
C6 C 0.4487(2) 0.1787(2) 0.63983(13) 0.0211(3) Uani 1 1 d . . . . .
C11 C 0.1657(3) 0.3086(2) 0.79050(13) 0.0253(4) Uani 1 1 d . . . . .
H11A H 0.216895 0.407100 0.796245 0.030 Uiso 1 1 calc R U . . .
H11B H 0.072938 0.369201 0.736992 0.030 Uiso 1 1 calc R U . . .
C2 C 0.7390(3) 0.2233(3) 0.50514(14) 0.0275(4) Uani 1 1 d . . . . .
H2 H 0.876091 0.217971 0.488100 0.033 Uiso 1 1 calc R U . . .
C13 C -0.2099(3) 0.3057(3) 1.04644(14) 0.0308(4) Uani 1 1 d . . . . .
H13A H -0.189641 0.169017 1.047014 0.046 Uiso 1 1 calc R U . . .
H13B H -0.357402 0.386016 1.060355 0.046 Uiso 1 1 calc R U . . .
H13C H -0.146560 0.309303 1.103138 0.046 Uiso 1 1 calc R U . . .
C3 C 0.6301(3) 0.2777(3) 0.42325(14) 0.0290(4) Uani 1 1 d . . . . .
H3 H 0.689946 0.311563 0.349822 0.035 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 C4 1.7384(17) . ?
F2 C9 1.382(2) . ?
F1 C9 1.3572(18) . ?
O2 C12 1.345(2) . ?
O2 C11 1.4439(19) . ?
O1 C10 1.210(2) . ?
O3 C12 1.202(2) . ?
C5 H5 0.9500 . ?
C5 C4 1.383(2) . ?
C5 C6 1.394(2) . ?
C1 C10 1.478(2) . ?
C1 C6 1.404(2) . ?
C1 C2 1.404(2) . ?
C10 C9 1.532(2) . ?
C4 C3 1.387(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.539(2) . ?
C7 C6 1.519(2) . ?
C7 C11 1.527(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.499(2) . ?
C12 C13 1.491(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C2 H2 0.9500 . ?
C2 C3 1.373(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C3 H3 0.9500 . ?

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
C12 O2 C11 115.69(13) . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.75(16) . . ?
C6 C5 H5 120.1 . . ?
C6 C1 C10 121.30(15) . . ?
C6 C1 C2 120.24(15) . . ?
C2 C1 C10 118.46(15) . . ?
O1 C10 C1 124.32(16) . . ?
O1 C10 C9 120.63(15) . . ?
C1 C10 C9 115.04(14) . . ?
C5 C4 Cl1 118.81(14) . . ?
C5 C4 C3 122.07(16) . . ?
C3 C4 Cl1 119.12(13) . . ?
C8 C7 H7 107.3 . . ?
C6 C7 H7 107.3 . . ?
C6 C7 C8 113.63(13) . . ?
C6 C7 C11 108.59(13) . . ?
C11 C7 H7 107.3 . . ?
C11 C7 C8 112.51(13) . . ?
C7 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 C7 112.58(13) . . ?
C9 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
F2 C9 C10 105.81(13) . . ?
F2 C9 C8 111.02(13) . . ?
F1 C9 F2 105.42(13) . . ?
F1 C9 C10 109.68(13) . . ?
F1 C9 C8 110.52(14) . . ?
C8 C9 C10 113.96(14) . . ?
O2 C12 C13 111.35(14) . . ?
O3 C12 O2 122.50(16) . . ?
O3 C12 C13 126.15(16) . . ?
C5 C6 C1 118.63(15) . . ?
C5 C6 C7 118.53(14) . . ?
C1 C6 C7 122.83(14) . . ?
O2 C11 C7 106.50(13) . . ?
O2 C11 H11A 110.4 . . ?
O2 C11 H11B 110.4 . . ?
C7 C11 H11A 110.4 . . ?
C7 C11 H11B 110.4 . . ?
H11A C11 H11B 108.6 . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.66(16) . . ?
C3 C2 H2 119.7 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C4 C3 H3 120.7 . . ?
C2 C3 C4 118.63(16) . . ?
C2 C3 H3 120.7 . . ?

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 C4 C3 C2 179.85(13) . . . . ?
O1 C10 C9 F2 97.00(18) . . . . ?
O1 C10 C9 F1 -16.3(2) . . . . ?
O1 C10 C9 C8 -140.74(17) . . . . ?
C5 C4 C3 C2 -0.7(3) . . . . ?
C1 C10 C9 F2 -81.89(16) . . . . ?
C1 C10 C9 F1 164.86(13) . . . . ?
C1 C10 C9 C8 40.4(2) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C10 C1 C6 C5 -179.76(14) . . . . ?
C10 C1 C6 C7 -0.6(2) . . . . ?
C10 C1 C2 C3 -179.38(15) . . . . ?
C4 C5 C6 C1 -0.9(2) . . . . ?
C4 C5 C6 C7 179.92(14) . . . . ?
C7 C8 C9 F2 65.76(17) . . . . ?
C7 C8 C9 F1 -177.62(13) . . . . ?
C7 C8 C9 C10 -53.58(18) . . . . ?
C8 C7 C6 C5 166.66(14) . . . . ?
C8 C7 C6 C1 -12.5(2) . . . . ?
C8 C7 C11 O2 -59.78(17) . . . . ?
C12 O2 C11 C7 -176.94(13) . . . . ?
C6 C5 C4 Cl1 -179.03(12) . . . . ?
C6 C5 C4 C3 1.6(3) . . . . ?
C6 C1 C10 O1 168.21(16) . . . . ?
C6 C1 C10 C9 -12.9(2) . . . . ?
C6 C1 C2 C3 1.4(3) . . . . ?
C6 C7 C8 C9 38.97(19) . . . . ?
C6 C7 C11 O2 173.56(12) . . . . ?
C11 O2 C12 O3 -0.5(2) . . . . ?
C11 O2 C12 C13 -179.33(13) . . . . ?
C11 C7 C8 C9 -84.95(17) . . . . ?
C11 C7 C6 C5 -67.32(19) . . . . ?
C11 C7 C6 C1 113.50(17) . . . . ?
C2 C1 C10 O1 -11.0(3) . . . . ?
C2 C1 C10 C9 167.88(14) . . . . ?
C2 C1 C6 C5 -0.6(2) . . . . ?
C2 C1 C6 C7 178.59(15) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CDCl3'
