# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_cd21345
_database_code_depnum_ccdc_archive 'CCDC 929444'
_audit_update_record             
;
2013-03-15 deposited with the CCDC.	2021-06-17 downloaded from the CCDC.
;
#TrackingRef 'cd21345.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H10 Cl F O2'
_chemical_formula_weight         216.63

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'
O O 0.0106 0.0060 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

loop_
_symmetry_equiv_pos_as_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'
'-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                   11.0279(12)
_cell_length_b                   7.6848(9)
_cell_length_c                   24.244(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2054.6(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3186
_cell_measurement_theta_min      4.994
_cell_measurement_theta_max      50.129

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.147
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    0.357
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.44416
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10955
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.50
_diffrn_reflns_theta_max         25.49
_reflns_number_total             1917
_reflns_number_gt                1646
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1171P)²+2.8792P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1917
_refine_ls_number_parameters     147
_refine_ls_number_restraints     97
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0826
_refine_ls_wR_factor_ref         0.2415
_refine_ls_wR_factor_gt          0.2336
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.1074(13) 1.2015(17) 0.4748(6) 0.094(3) Uani 0.50 1 d PU A 1
F1 F 0.0464(19) 0.767(4) 0.4076(13) 0.068(4) Uani 0.50 1 d PU B 1
Cl1' Cl 0.1218(16) 1.2501(18) 0.4651(6) 0.103(3) Uani 0.50 1 d PU A 2
F1' F 0.085(2) 0.774(4) 0.4084(14) 0.080(5) Uani 0.50 1 d PU B 2
O1 O 0.1409(2) 0.4498(3) 0.29135(12) 0.0509(7) Uani 1 1 d U . .
H1 H 0.1418 0.3480 0.3015 0.076 Uiso 1 1 calc R . .
O2 O 0.1369(2) 1.0886(3) 0.30500(11) 0.0478(7) Uani 1 1 d U . .
H2 H 0.2042 1.0515 0.2967 0.072 Uiso 1 1 calc R . .
C1 C 0.0439(4) 0.5396(5) 0.3180(2) 0.0607(11) Uani 1 1 d U . .
H1A H 0.0387 0.5042 0.3564 0.073 Uiso 1 1 calc R . .
H1B H -0.0324 0.5120 0.3002 0.073 Uiso 1 1 calc R . .
C2 C 0.0681(3) 0.7317(4) 0.31438(17) 0.0469(9) Uani 1 1 d DU B .
H2A H 0.0763 0.7800 0.2794 0.056 Uiso 1 1 calc R . .
C3 C 0.0783(3) 0.8355(4) 0.35650(15) 0.0461(9) Uani 1 1 d DU . .
C4 C 0.1044(3) 1.0263(4) 0.35844(15) 0.0457(9) Uani 1 1 d U B .
H4 H 0.1717 1.0474 0.3840 0.055 Uiso 1 1 calc R . .
C5 C -0.0061(3) 1.1273(4) 0.37783(14) 0.0423(8) Uani 1 1 d U . .
C6 C -0.1079(3) 1.1331(5) 0.34478(19) 0.0540(10) Uani 1 1 d U B .
H6 H -0.1069 1.0725 0.3116 0.065 Uiso 1 1 calc R . .
C7 C -0.2101(4) 1.2238(6) 0.3586(2) 0.0731(14) Uani 1 1 d U . .
H7 H -0.2762 1.2292 0.3348 0.088 Uiso 1 1 calc R B .
C8 C -0.2118(5) 1.3084(7) 0.4099(2) 0.0776(15) Uani 1 1 d U B .
H8 H -0.2813 1.3672 0.4210 0.093 Uiso 1 1 calc R . .
C9 C -0.1138(5) 1.3054(8) 0.4433(2) 0.0818(15) Uani 1 1 d U . .
H9 H -0.1159 1.3625 0.4771 0.098 Uiso 1 1 calc R B .
C10 C -0.0103(4) 1.2176(6) 0.42726(18) 0.0630(11) Uani 1 1 d U A .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.104(3) 0.121(8) 0.058(3) -0.021(4) -0.028(3) 0.028(4)
F1 0.099(11) 0.048(4) 0.058(4) 0.016(3) 0.025(8) 0.003(7)
Cl1' 0.138(5) 0.102(6) 0.070(5) -0.026(4) -0.033(4) 0.024(4)
F1' 0.119(14) 0.058(5) 0.062(4) 0.008(4) 0.007(10) 0.012(9)
O1 0.0471(14) 0.0218(11) 0.0838(18) -0.0038(11) -0.0043(12) 0.0012(10)
O2 0.0434(13) 0.0273(12) 0.0728(17) 0.0094(11) 0.0133(11) 0.0041(10)
C1 0.056(2) 0.0256(17) 0.100(3) -0.0018(18) 0.007(2) -0.0032(15)
C2 0.055(2) 0.0260(16) 0.060(2) 0.0033(15) -0.0018(17) 0.0019(14)
C3 0.0513(19) 0.0265(16) 0.061(2) 0.0073(15) 0.0091(16) 0.0064(14)
C4 0.0456(19) 0.0323(17) 0.059(2) -0.0010(15) -0.0023(15) 0.0041(14)
C5 0.0460(19) 0.0265(15) 0.0544(19) 0.0009(14) 0.0019(15) 0.0006(13)
C6 0.049(2) 0.0403(19) 0.073(2) 0.0013(18) 0.0004(18) 0.0017(15)
C7 0.043(2) 0.066(3) 0.111(4) 0.029(3) 0.008(2) 0.0078(19)
C8 0.077(3) 0.072(3) 0.083(3) 0.018(3) 0.035(3) 0.026(3)
C9 0.103(4) 0.079(3) 0.064(3) 0.003(2) 0.027(3) 0.030(3)
C10 0.077(3) 0.058(2) 0.054(2) -0.0009(19) 0.002(2) 0.013(2)

_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 C10 1.740(14) . ?
F1 C3 1.39(3) . ?
Cl1' C10 1.739(18) . ?
F1' C3 1.34(3) . ?
O1 C1 1.429(5) . ?
O1 H1 0.8200 . ?
O2 C4 1.427(4) . ?
O2 H2 0.8200 . ?
C1 C2 1.503(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.301(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.495(5) . ?
C4 C5 1.519(5) . ?
C4 H4 0.9800 . ?
C5 C6 1.380(5) . ?
C5 C10 1.386(5) . ?
C6 C7 1.367(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.404(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.351(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.381(7) . ?
C9 H9 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
C1 O1 H1 109.5 . . ?
C4 O2 H2 109.5 . . ?
O1 C1 C2 108.3(3) . . ?
O1 C1 H1A 110.0 . . ?
C2 C1 H1A 110.0 . . ?
O1 C1 H1B 110.0 . . ?
C2 C1 H1B 110.0 . . ?
H1A C1 H1B 108.4 . . ?
C3 C2 C1 124.8(4) . . ?
C3 C2 H2A 117.6 . . ?
C1 C2 H2A 117.6 . . ?
C2 C3 F1' 121.6(15) . . ?
C2 C3 F1 116.4(14) . . ?
F1' C3 F1 17.9(18) . . ?
C2 C3 C4 130.0(3) . . ?
F1' C3 C4 107.7(15) . . ?
F1 C3 C4 113.1(14) . . ?
O2 C4 C3 110.4(3) . . ?
O2 C4 C5 108.1(3) . . ?
C3 C4 C5 110.9(3) . . ?
O2 C4 H4 109.1 . . ?
C3 C4 H4 109.1 . . ?
C5 C4 H4 109.1 . . ?
C6 C5 C10 117.3(4) . . ?
C6 C5 C4 119.3(3) . . ?
C10 C5 C4 123.4(3) . . ?
C7 C6 C5 123.1(4) . . ?
C7 C6 H6 118.5 . . ?
C5 C6 H6 118.5 . . ?
C6 C7 C8 117.6(5) . . ?
C6 C7 H7 121.2 . . ?
C8 C7 H7 121.2 . . ?
C9 C8 C7 120.8(4) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 120.1(5) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C5 121.0(4) . . ?
C9 C10 Cl1' 118.3(7) . . ?
C5 C10 Cl1' 120.0(7) . . ?
C9 C10 Cl1 117.7(6) . . ?
C5 C10 Cl1 120.8(6) . . ?
Cl1' C10 Cl1 15.5(8) . . ?

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 -121.5(4) . . . . ?
C1 C2 C3 F1' 9.6(13) . . . . ?
C1 C2 C3 F1 -10.0(12) . . . . ?
C1 C2 C3 C4 178.7(4) . . . . ?
C2 C3 C4 O2 -8.7(5) . . . . ?
F1' C3 C4 O2 161.6(11) . . . . ?
F1 C3 C4 O2 179.8(11) . . . . ?
C2 C3 C4 C5 111.1(4) . . . . ?
F1' C3 C4 C5 -78.6(11) . . . . ?
F1 C3 C4 C5 -60.4(11) . . . . ?
O2 C4 C5 C6 54.1(4) . . . . ?
C3 C4 C5 C6 -67.1(4) . . . . ?
O2 C4 C5 C10 -124.9(4) . . . . ?
C3 C4 C5 C10 113.9(4) . . . . ?
C10 C5 C6 C7 0.5(6) . . . . ?
C4 C5 C6 C7 -178.6(4) . . . . ?
C5 C6 C7 C8 -2.6(6) . . . . ?
C6 C7 C8 C9 2.5(7) . . . . ?
C7 C8 C9 C10 -0.4(8) . . . . ?
C8 C9 C10 C5 -1.9(8) . . . . ?
C8 C9 C10 Cl1' 168.3(6) . . . . ?
C8 C9 C10 Cl1 -174.1(6) . . . . ?
C6 C5 C10 C9 1.8(6) . . . . ?
C4 C5 C10 C9 -179.1(4) . . . . ?
C6 C5 C10 Cl1' -168.2(5) . . . . ?
C4 C5 C10 Cl1' 10.8(7) . . . . ?
C6 C5 C10 Cl1 173.8(6) . . . . ?
C4 C5 C10 Cl1 -7.2(7) . . . . ?

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
O1 H1 O2 0.82 2.00 2.796(3) 164.8 1_545
O2 H2 O1 0.82 1.88 2.693(3) 169.2 8_665

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.818
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.087
