# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_tw2005g
_database_code_depnum_ccdc_archive 'CCDC 2043588'
loop_
_audit_author_name
_audit_author_address
'Benson Kariuki'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2020-11-10 deposited with the CCDC.	2021-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 F2'
_chemical_formula_weight         218.24

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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'I a'
_space_group_name_Hall           'I -2ya'

_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+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'

_cell_length_a                   8.4950(7)
_cell_length_b                   5.4887(4)
_cell_length_c                   24.023(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.001(9)
_cell_angle_gamma                90
_cell_volume                     1109.20(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2156
_cell_measurement_theta_min      5.6550
_cell_measurement_theta_max      76.7500

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.113
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.816
_shelx_estimated_absorpt_T_min   0.913
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_T_min  0.767
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4429
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.716
_diffrn_reflns_theta_max         76.630
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.711
_diffrn_reflns_point_group_measured_fraction_full 0.729
_reflns_number_total             1668
_reflns_number_gt                1366
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.435
_reflns_Friedel_fraction_max     0.432
_reflns_Friedel_fraction_full    0.457

_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       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_structure_solution    SHELXS
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.1684P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 312 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1668
_refine_ls_number_parameters     145
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0772
_refine_ls_wR_factor_ref         0.2388
_refine_ls_wR_factor_gt          0.2231
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.090
_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
C1 C 0.4780(6) 0.7105(9) 0.4182(2) 0.0464(12) Uani 1 1 d . . . . .
C2 C 0.5257(8) 0.9094(10) 0.3880(3) 0.0553(14) Uani 1 1 d . . . . .
H2 H 0.601186 1.022525 0.405820 0.066 Uiso 1 1 calc R U . . .
C3 C 0.4624(10) 0.9403(12) 0.3322(3) 0.0653(17) Uani 1 1 d . . . . .
H3 H 0.494565 1.075193 0.311768 0.078 Uiso 1 1 calc R U . . .
C4 C 0.3528(8) 0.7764(13) 0.3061(3) 0.0602(15) Uani 1 1 d . . . . .
H4 H 0.310649 0.797384 0.267618 0.072 Uiso 1 1 calc R U . . .
C5 C 0.3042(9) 0.5798(12) 0.3364(3) 0.0650(17) Uani 1 1 d . . . . .
H5 H 0.227591 0.467736 0.318847 0.078 Uiso 1 1 calc R U . . .
C6 C 0.3674(7) 0.5499(11) 0.3913(3) 0.0555(14) Uani 1 1 d . . . . .
H6 H 0.334520 0.415000 0.411612 0.067 Uiso 1 1 calc R U . . .
C7 C 0.5434(6) 0.6827(10) 0.4796(2) 0.0463(12) Uani 1 1 d . . . . .
C8 C 0.4456(6) 0.8046(10) 0.5198(3) 0.0502(12) Uani 1 1 d . . . . .
H8A H 0.437039 0.980613 0.510900 0.060 Uiso 1 1 calc R U . . .
H8B H 0.336897 0.735446 0.513944 0.060 Uiso 1 1 calc R U . . .
C9 C 0.5147(6) 0.7742(9) 0.5808(2) 0.0464(11) Uani 1 1 d . . . . .
C10 C 0.4707(7) 0.5819(11) 0.6128(3) 0.0552(14) Uani 1 1 d . . . . .
H10 H 0.395611 0.465411 0.596342 0.066 Uiso 1 1 calc R U . . .
C11 C 0.5354(9) 0.5592(12) 0.6685(3) 0.0632(16) Uani 1 1 d . . . . .
H11 H 0.504603 0.427055 0.690135 0.076 Uiso 1 1 calc R U . . .
C12 C 0.6458(9) 0.7291(14) 0.6933(3) 0.0648(17) Uani 1 1 d . . . . .
H12 H 0.688703 0.714089 0.731829 0.078 Uiso 1 1 calc R U . . .
C13 C 0.6926(8) 0.9193(12) 0.6616(3) 0.0595(15) Uani 1 1 d . . . . .
H13 H 0.769825 1.032923 0.677951 0.071 Uiso 1 1 calc R U . . .
C14 C 0.6263(7) 0.9435(11) 0.6057(3) 0.0542(14) Uani 1 1 d . . . . .
H14 H 0.656936 1.076026 0.584131 0.065 Uiso 1 1 calc R U . . .
F1 F 0.6969(4) 0.7612(7) 0.48908(18) 0.0581(9) Uani 1 1 d . . . . .
F2 F 0.5538(4) 0.4339(5) 0.49152(18) 0.0576(9) 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
C1 C6 1.381(8) . ?
C1 C2 1.401(8) . ?
C1 C7 1.510(8) . ?
C2 C3 1.383(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.382(11) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(10) . ?
C4 H4 0.9500 . ?
C5 C6 1.364(10) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 F1 1.362(6) . ?
C7 F2 1.395(6) . ?
C7 C8 1.515(7) . ?
C8 C9 1.511(8) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.387(8) . ?
C9 C14 1.401(8) . ?
C10 C11 1.379(10) . ?
C10 H10 0.9500 . ?
C11 C12 1.396(11) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(11) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(9) . ?
C13 H13 0.9500 . ?
C14 H14 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
C6 C1 C2 118.8(6) . . ?
C6 C1 C7 121.8(5) . . ?
C2 C1 C7 119.4(5) . . ?
C3 C2 C1 119.7(6) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 120.5(6) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.7(7) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 119.5(6) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 121.8(6) . . ?
C5 C6 H6 119.1 . . ?
C1 C6 H6 119.1 . . ?
F1 C7 F2 104.1(4) . . ?
F1 C7 C1 110.2(4) . . ?
F2 C7 C1 107.7(4) . . ?
F1 C7 C8 110.6(4) . . ?
F2 C7 C8 109.0(4) . . ?
C1 C7 C8 114.7(4) . . ?
C9 C8 C7 113.4(4) . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C10 C9 C14 119.1(6) . . ?
C10 C9 C8 121.6(5) . . ?
C14 C9 C8 119.3(5) . . ?
C11 C10 C9 120.3(6) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 120.5(6) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 119.8(7) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 119.8(6) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C9 120.6(6) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?

_refine_diff_density_max         0.385
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.080



####################################################################### 
# 
# 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_tw2007c
_database_code_depnum_ccdc_archive 'CCDC 2043555'
loop_
_audit_author_name
_audit_author_address
'Benson Kariuki'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2020-11-10 deposited with the CCDC.	2021-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H7 F O'
_chemical_formula_weight         150.15

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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                   7.8286(3)
_cell_length_b                   5.5513(2)
_cell_length_c                   16.0794(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.759(4)
_cell_angle_gamma                90
_cell_volume                     696.38(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2156
_cell_measurement_theta_min      5.6550
_cell_measurement_theta_max      76.7500

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.239
_exptl_crystal_size_mid          0.169
_exptl_crystal_size_min          0.101
_exptl_absorpt_coefficient_mu    0.928
_shelx_estimated_absorpt_T_min   0.809
_shelx_estimated_absorpt_T_max   0.912
_exptl_absorpt_correction_T_min  0.767
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5288
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         5.522
_diffrn_reflns_theta_max         76.705
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1445
_reflns_number_gt                1259
_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       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_structure_solution    shelxs
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0496P)²+0.1888P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1445
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1019
_refine_ls_wR_factor_gt          0.0958
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_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
C1 C 0.20802(16) -0.0604(2) 1.02690(8) 0.0335(3) Uani 1 1 d . . . . .
C2 C 0.27958(18) 0.1894(2) 1.00897(8) 0.0371(3) Uani 1 1 d . . . . .
H2 H 0.182061 0.303263 0.995871 0.045 Uiso 1 1 calc R U . . .
C3 C 0.37959(17) 0.2685(2) 1.08946(9) 0.0361(3) Uani 1 1 d . . . . .
H3A H 0.503801 0.238070 1.087495 0.043 Uiso 1 1 calc R U . . .
H3B H 0.361420 0.441647 1.100498 0.043 Uiso 1 1 calc R U . . .
C4 C 0.30517(15) 0.1130(2) 1.15453(8) 0.0303(3) Uani 1 1 d . . . . .
C5 C 0.21025(16) -0.0782(2) 1.11812(8) 0.0300(3) Uani 1 1 d . . . . .
C6 C 0.32389(17) 0.1353(2) 1.24076(8) 0.0351(3) Uani 1 1 d . . . . .
H6 H 0.386326 0.265895 1.266543 0.042 Uiso 1 1 calc R U . . .
C7 C 0.24913(17) -0.0378(3) 1.28848(8) 0.0364(3) Uani 1 1 d . . . . .
H7 H 0.261198 -0.024502 1.347581 0.044 Uiso 1 1 calc R U . . .
C8 C 0.15677(18) -0.2309(3) 1.25185(9) 0.0370(3) Uani 1 1 d . . . . .
H8 H 0.108286 -0.347869 1.286035 0.044 Uiso 1 1 calc R U . . .
C9 C 0.13562(17) -0.2524(2) 1.16600(9) 0.0344(3) Uani 1 1 d . . . . .
H9 H 0.072074 -0.382141 1.140335 0.041 Uiso 1 1 calc R U . . .
O1 O 0.16018(14) -0.2088(2) 0.97467(6) 0.0449(3) Uani 1 1 d . . . . .
F1 F 0.38067(12) 0.18196(17) 0.94146(5) 0.0498(3) 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
C1 O1 1.2131(17) . ?
C1 C5 1.4689(17) . ?
C1 C2 1.5319(19) . ?
C2 F1 1.3961(15) . ?
C2 C3 1.521(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.5099(18) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C6 1.3876(18) . ?
C4 C5 1.3962(18) . ?
C5 C9 1.3942(18) . ?
C6 C7 1.389(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.396(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.382(2) . ?
C8 H8 0.9500 . ?
C9 H9 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
O1 C1 C5 128.55(13) . . ?
O1 C1 C2 125.52(12) . . ?
C5 C1 C2 105.93(11) . . ?
F1 C2 C3 112.66(12) . . ?
F1 C2 C1 111.05(11) . . ?
C3 C2 C1 105.76(10) . . ?
F1 C2 H2 109.1 . . ?
C3 C2 H2 109.1 . . ?
C1 C2 H2 109.1 . . ?
C4 C3 C2 102.93(11) . . ?
C4 C3 H3A 111.2 . . ?
C2 C3 H3A 111.2 . . ?
C4 C3 H3B 111.2 . . ?
C2 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
C6 C4 C5 119.68(12) . . ?
C6 C4 C3 128.80(12) . . ?
C5 C4 C3 111.50(11) . . ?
C9 C5 C4 121.92(12) . . ?
C9 C5 C1 128.84(12) . . ?
C4 C5 C1 109.24(11) . . ?
C4 C6 C7 118.41(12) . . ?
C4 C6 H6 120.8 . . ?
C7 C6 H6 120.8 . . ?
C6 C7 C8 121.70(12) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C9 C8 C7 120.19(12) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C5 118.08(12) . . ?
C8 C9 H9 121.0 . . ?
C5 C9 H9 121.0 . . ?

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 F1 -37.23(18) . . . . ?
C5 C1 C2 F1 142.87(11) . . . . ?
O1 C1 C2 C3 -159.75(13) . . . . ?
C5 C1 C2 C3 20.34(13) . . . . ?
F1 C2 C3 C4 -142.33(11) . . . . ?
C1 C2 C3 C4 -20.84(13) . . . . ?
C2 C3 C4 C6 -167.01(13) . . . . ?
C2 C3 C4 C5 14.79(14) . . . . ?
C6 C4 C5 C9 -1.35(19) . . . . ?
C3 C4 C5 C9 177.03(11) . . . . ?
C6 C4 C5 C1 179.41(11) . . . . ?
C3 C4 C5 C1 -2.21(14) . . . . ?
O1 C1 C5 C9 -10.5(2) . . . . ?
C2 C1 C5 C9 169.41(13) . . . . ?
O1 C1 C5 C4 168.69(13) . . . . ?
C2 C1 C5 C4 -11.41(13) . . . . ?
C5 C4 C6 C7 1.12(18) . . . . ?
C3 C4 C6 C7 -176.95(12) . . . . ?
C4 C6 C7 C8 -0.06(19) . . . . ?
C6 C7 C8 C9 -0.8(2) . . . . ?
C7 C8 C9 C5 0.6(2) . . . . ?
C4 C5 C9 C8 0.46(19) . . . . ?
C1 C5 C9 C8 179.54(12) . . . . ?

_refine_diff_density_max         0.189
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.039



####################################################################### 
# 
# 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_tw2111
_database_code_depnum_ccdc_archive 'CCDC 2072599'
loop_
_audit_author_name
_audit_author_address
'Benson Kariuki'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2021-03-23 deposited with the CCDC.	2021-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H9 F N2 O3'
_chemical_formula_weight         224.19

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'
N N 0.0311 0.0180 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   10.1310(6)
_cell_length_b                   6.6921(5)
_cell_length_c                   15.4050(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1044.42(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1145
_cell_measurement_theta_min      5.2020
_cell_measurement_theta_max      73.9810

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.076
_exptl_absorpt_coefficient_mu    1.019
_shelx_estimated_absorpt_T_min   0.646
_shelx_estimated_absorpt_T_max   0.927
_exptl_absorpt_correction_T_min  0.620
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4270
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         5.226
_diffrn_reflns_theta_max         76.960
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1187
_reflns_number_gt                905
_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       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    SHELXS
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0832P)²+0.0257P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1187
_refine_ls_number_parameters     112
_refine_ls_number_restraints     86
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1433
_refine_ls_wR_factor_gt          0.1260
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.092
_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
C1 C 0.43846(19) 0.250000 0.61304(12) 0.0599(5) Uani 1 2 d S T P . .
C2 C 0.3970(2) 0.250000 0.52770(13) 0.0601(4) Uani 1 2 d S T P . .
H2 H 0.307656 0.250000 0.513936 0.072 Uiso 1 2 calc R U P . .
C3 C 0.49157(19) 0.250000 0.46348(12) 0.0581(4) Uani 1 2 d S T P . .
H3 H 0.465998 0.250000 0.405498 0.070 Uiso 1 2 calc R U P . .
C4 C 0.62495(18) 0.250000 0.48467(12) 0.0569(4) Uani 1 2 d S T P . .
C5 C 0.6639(2) 0.250000 0.57118(13) 0.0644(5) Uani 1 2 d S T P . .
H5 H 0.753148 0.250000 0.585282 0.077 Uiso 1 2 calc R U P . .
C6 C 0.5701(2) 0.250000 0.63622(12) 0.0649(5) Uani 1 2 d S T P . .
H6 H 0.594975 0.250000 0.694325 0.078 Uiso 1 2 calc R U P . .
C7 C 0.7237(2) 0.250000 0.41437(13) 0.0654(5) Uani 1 2 d S TU P . .
C8 C 0.8270(3) 0.250000 0.28934(17) 0.0859(7) Uani 1 2 d S TU P . .
H8A H 0.852474 0.371066 0.259036 0.103 Uiso 0.5 1 calc R U P . .
H8B H 0.820575 0.141926 0.247596 0.103 Uiso 0.5 1 calc R U P . .
C9 C 0.9288(3) 0.1985(5) 0.3613(2) 0.0852(12) Uani 0.5 1 d . U P . .
H9 H 0.968507 0.066781 0.351644 0.102 Uiso 0.5 1 calc R U P . .
C10 C 1.0314(4) 0.3577(8) 0.3656(3) 0.1090(13) Uani 0.5 1 d . U P . .
H10A H 1.069956 0.375481 0.308479 0.131 Uiso 0.5 1 calc R U P . .
H10B H 0.990110 0.482791 0.382181 0.131 Uiso 0.5 1 calc R U P . .
N1 N 0.3392(2) 0.250000 0.68222(14) 0.0775(5) Uani 1 2 d S T P . .
N2 N 0.6997(2) 0.2785(4) 0.33499(14) 0.0625(7) Uani 0.5 1 d . U P . .
O1 O 0.22260(17) 0.250000 0.66115(14) 0.0946(6) Uani 1 2 d S T P . .
O2 O 0.3755(2) 0.250000 0.75673(13) 0.1151(8) Uani 1 2 d S T P . .
O3 O 0.84961(19) 0.2010(3) 0.43945(14) 0.0788(9) Uani 0.5 1 d . U P . .
F1 F 1.1271(3) 0.3143(7) 0.4224(3) 0.161(2) Uani 0.5 1 d . U P . .


_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 C2 1.380(3) . ?
C1 C6 1.380(3) . ?
C1 N1 1.465(3) . ?
C2 C3 1.377(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(3) . ?
C4 C7 1.475(3) . ?
C5 C6 1.381(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N2 1.261(3) . ?
C7 O3 1.372(3) . ?
C8 N2 1.482(3) . ?
C8 C9 1.553(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8A 0.9700 7_565 ?
C8 H8B 0.9700 7_565 ?
C9 O3 1.447(4) . ?
C9 C10 1.490(5) . ?
C9 H9 0.9800 . ?
C10 F1 1.337(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
N1 O2 1.205(3) . ?
N1 O1 1.225(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
C2 C1 C6 122.70(18) . . ?
C2 C1 N1 118.96(19) . . ?
C6 C1 N1 118.34(19) . . ?
C3 C2 C1 118.23(18) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 120.49(17) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 120.07(18) . . ?
C5 C4 C7 120.78(18) . . ?
C3 C4 C7 119.15(17) . . ?
C6 C5 C4 120.02(18) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C1 C6 C5 118.50(18) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
N2 C7 O3 119.2(2) . . ?
N2 C7 C4 125.5(2) . . ?
O3 C7 C4 115.08(18) . . ?
N2 C8 C9 105.6(2) . . ?
N2 C8 H8A 110.6 . . ?
C9 C8 H8A 110.6 . . ?
N2 C8 H8B 110.6 . . ?
C9 C8 H8B 110.6 . . ?
H8A C8 H8B 108.8 . . ?
N2 C8 H8A 124.59(10) . 7_565 ?
C9 C8 H8A 88.94(13) . 7_565 ?
H8A C8 H8A 113.3 . 7_565 ?
H8B C8 H8A 22.5 . 7_565 ?
N2 C8 H8B 99.21(13) . 7_565 ?
C9 C8 H8B 133.11(13) . 7_565 ?
H8A C8 H8B 22.5 . 7_565 ?
H8B C8 H8B 96.4 . 7_565 ?
H8A C8 H8B 108.8 7_565 7_565 ?
O3 C9 C10 110.0(3) . . ?
O3 C9 C8 102.9(2) . . ?
C10 C9 C8 109.7(3) . . ?
O3 C9 H9 111.3 . . ?
C10 C9 H9 111.3 . . ?
C8 C9 H9 111.3 . . ?
F1 C10 C9 112.3(4) . . ?
F1 C10 H10A 109.1 . . ?
C9 C10 H10A 109.1 . . ?
F1 C10 H10B 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
F1 C10 H9 147.8(7) . 7_565 ?
C9 C10 H9 83.7(5) . 7_565 ?
H10A C10 H9 90.0 . 7_565 ?
H10B C10 H9 38.9 . 7_565 ?
O2 N1 O1 123.1(2) . . ?
O2 N1 C1 118.9(2) . . ?
O1 N1 C1 118.0(2) . . ?
C7 N2 C8 105.8(2) . . ?
C7 O3 C9 106.5(2) . . ?

_refine_diff_density_max         0.160
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.038



