# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_dan9182
_database_code_depnum_ccdc_archive 'CCDC 2346847'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut University of Muenster
Germany
;
_audit_update_record             
;
2024-04-09 deposited with the CCDC.	2024-06-24 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H9 Cl F3 N O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         235.59
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_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'

_cell_length_a                   5.4353(2)
_cell_length_b                   7.0050(3)
_cell_length_c                   23.8253(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     907.13(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2122
_cell_measurement_theta_min      6.5870
_cell_measurement_theta_max      66.6339
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480

_exptl_absorpt_coefficient_mu    4.129
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_T_max  0.92

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'fine-focus sealed tube'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Kappa CCD APEXII'
_diffrn_measurement_method       'phi / omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            7754
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_theta_min         6.59
_diffrn_reflns_theta_max         66.69
_diffrn_reflns_theta_full        66.69
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27

_refine_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_number_total             1612
_reflns_number_gt                1461
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_gt          0.0643
_refine_ls_wR_factor_ref         0.0661
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_number_reflns         1612
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0339P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.188
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 551 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.040(12)

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

_computing_data_collection       'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 -0.30935(14) 0.17038(11) 0.44169(3) 0.01851(19) Uani d . . . 1 . .
F F1 0.6070(4) 0.7632(3) 0.26757(8) 0.0294(5) Uani d . . . 1 . .
F F2 0.2595(4) 0.8877(3) 0.29082(8) 0.0308(5) Uani d . . . 1 . .
F F3 0.2694(4) 0.6658(3) 0.22928(7) 0.0293(5) Uani d . . . 1 . .
N N1 0.1828(6) 0.3868(4) 0.42441(10) 0.0156(6) Uani d . . . 1 . .
H H1A 0.337(8) 0.372(5) 0.4424(16) 0.022(9) Uiso d . . . 1 . .
H H1B 0.087(7) 0.309(6) 0.4449(14) 0.013(8) Uiso d . . . 1 . .
O O1 0.5165(4) 0.6529(3) 0.45445(8) 0.0185(5) Uani d . . . 1 . .
O O2 0.2823(5) 0.8959(4) 0.42417(9) 0.0211(5) Uani d . . . 1 . .
H H2A 0.397(9) 0.969(7) 0.4290(18) 0.031(12) Uiso d . . . 1 . .
O O3 0.3626(4) 0.5921(3) 0.31820(8) 0.0165(5) Uani d . . . 1 . .
C C2 0.0985(6) 0.5908(5) 0.42677(12) 0.0150(7) Uani d . . . 1 . .
H H2 -0.0224 0.6081 0.458 0.018 Uiso calc U . R 1 . .
C C3 -0.0270(6) 0.6219(5) 0.37046(12) 0.0163(7) Uani d . . . 1 . .
H H3A -0.1999 0.5777 0.3715 0.02 Uiso calc U . R 1 . .
H H3B -0.0236 0.7584 0.3597 0.02 Uiso calc U . R 1 . .
C C4 0.1252(6) 0.5021(5) 0.33013(13) 0.0171(7) Uani d . . . 1 . .
H H4 0.0325 0.4713 0.295 0.021 Uiso calc U . R 1 . .
C C5 0.1857(6) 0.3241(5) 0.36382(11) 0.0168(6) Uani d . . . 1 . .
H H5A 0.0613 0.2233 0.3572 0.02 Uiso calc U . R 1 . .
H H5B 0.3497 0.274 0.3534 0.02 Uiso calc U . R 1 . .
C C6 0.3255(6) 0.7159(4) 0.43673(12) 0.0151(6) Uani d . . . 1 . .
C C7 0.3712(6) 0.7237(5) 0.27766(13) 0.0201(8) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C7 . 1.333(4) ?
F2 C7 . 1.336(4) ?
F3 C7 . 1.341(4) ?
N1 C2 . 1.502(4) ?
N1 C5 . 1.509(4) ?
N1 H1A . 0.95(4) ?
N1 H1B . 0.90(4) ?
O1 C6 . 1.205(4) ?
O2 C6 . 1.317(4) ?
O2 H2A . 0.82(5) ?
O3 C7 . 1.336(4) ?
O3 C4 . 1.464(4) ?
C2 C3 . 1.521(4) ?
C2 C6 . 1.532(4) ?
C2 H2 . 1.0 ?
C3 C4 . 1.520(5) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C5 . 1.519(5) ?
C4 H4 . 1.0 ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C5 . . 108.4(2) ?
C2 N1 H1A . . 111.(2) ?
C5 N1 H1A . . 113.(2) ?
C2 N1 H1B . . 112.(2) ?
C5 N1 H1B . . 110.(2) ?
H1A N1 H1B . . 102.(3) ?
C6 O2 H2A . . 116.(3) ?
C7 O3 C4 . . 117.9(2) ?
N1 C2 C3 . . 103.9(3) ?
N1 C2 C6 . . 107.7(3) ?
C3 C2 C6 . . 114.6(3) ?
N1 C2 H2 . . 110.1 ?
C3 C2 H2 . . 110.1 ?
C6 C2 H2 . . 110.1 ?
C4 C3 C2 . . 103.6(3) ?
C4 C3 H3A . . 111.0 ?
C2 C3 H3A . . 111.0 ?
C4 C3 H3B . . 111.0 ?
C2 C3 H3B . . 111.0 ?
H3A C3 H3B . . 109.0 ?
O3 C4 C5 . . 105.4(3) ?
O3 C4 C3 . . 111.4(3) ?
C5 C4 C3 . . 103.7(3) ?
O3 C4 H4 . . 112.0 ?
C5 C4 H4 . . 112.0 ?
C3 C4 H4 . . 112.0 ?
N1 C5 C4 . . 105.3(3) ?
N1 C5 H5A . . 110.7 ?
C4 C5 H5A . . 110.7 ?
N1 C5 H5B . . 110.7 ?
C4 C5 H5B . . 110.7 ?
H5A C5 H5B . . 108.8 ?
O1 C6 O2 . . 125.7(3) ?
O1 C6 C2 . . 122.6(3) ?
O2 C6 C2 . . 111.7(3) ?
F1 C7 F2 . . 107.5(3) ?
F1 C7 O3 . . 107.9(3) ?
F2 C7 O3 . . 114.1(3) ?
F1 C7 F3 . . 107.7(3) ?
F2 C7 F3 . . 105.9(3) ?
O3 C7 F3 . . 113.5(3) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C2 C3 . . . . 18.5(3) ?
C5 N1 C2 C6 . . . . -103.5(3) ?
N1 C2 C3 C4 . . . . -35.2(3) ?
C6 C2 C3 C4 . . . . 82.1(3) ?
C7 O3 C4 C5 . . . . 163.5(3) ?
C7 O3 C4 C3 . . . . -84.7(3) ?
C2 C3 C4 O3 . . . . -74.1(3) ?
C2 C3 C4 C5 . . . . 38.7(3) ?
C2 N1 C5 C4 . . . . 5.4(3) ?
O3 C4 C5 N1 . . . . 89.9(3) ?
C3 C4 C5 N1 . . . . -27.2(3) ?
N1 C2 C6 O1 . . . . -18.1(4) ?
C3 C2 C6 O1 . . . . -133.2(3) ?
N1 C2 C6 O2 . . . . 162.5(2) ?
C3 C2 C6 O2 . . . . 47.5(4) ?
C4 O3 C7 F1 . . . . -170.0(3) ?
C4 O3 C7 F2 . . . . 70.7(4) ?
C4 O3 C7 F3 . . . . -50.7(4) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1A Cl1 1_655 0.95(4) 2.39(4) 3.176(3) 141.(3) ?
N1 H1B Cl1 . 0.90(4) 2.36(4) 3.102(3) 140.(3) ?
O2 H2A Cl1 1_665 0.82(5) 2.15(5) 2.966(3) 178.(4) ?

####################################################################### 
# 
# 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_vd388
_database_code_depnum_ccdc_archive 'CCDC 2358277'
loop_
_audit_author_name
_audit_author_address
'Svitlana Shishkina'
;SSI Institute for Single Crystals
Ukraine
;
_audit_update_record             
;
2024-05-26 deposited with the CCDC.	2024-06-24 downloaded from the CCDC.
;
_audit_creation_date             2024-05-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl, C6 H9 F3 N O3'
_chemical_formula_sum            'C6 H9 Cl F3 N O3'
_chemical_formula_weight         235.59
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
N N 0.0061 0.0033 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_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'

_cell_length_a                   5.4474(2)
_cell_length_b                   7.0132(3)
_cell_length_c                   23.9996(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     916.87(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5334
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      24.50
_cell_measurement_theta_min      3.03
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.916
_exptl_absorpt_coefficient_mu    0.447
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            12961
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.990
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_min         3.026
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.641
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1557
_reflns_number_total             1625
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 589 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1625
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0277
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0332P)²+0.2123P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0637
_refine_ls_wR_factor_ref         0.0645
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C1(H1C,H1D), C3(H3A,H3B)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.68889(12) 0.83005(9) 0.44186(3) 0.02751(19) Uani 1 1 d . . . . .
F1 F 0.2641(4) 0.3356(3) 0.23075(7) 0.0481(5) Uani 1 1 d . . . . .
F2 F 0.6008(4) 0.2391(3) 0.26759(8) 0.0496(6) Uani 1 1 d . . . . .
F3 F 0.2553(4) 0.1143(3) 0.29108(8) 0.0511(6) Uani 1 1 d . . . . .
O1 O 0.5147(4) 0.3466(3) 0.45419(8) 0.0271(4) Uani 1 1 d . . . . .
O2 O 0.2815(4) 0.1040(3) 0.42481(9) 0.0305(5) Uani 1 1 d . . . . .
H2 H 0.408910 0.039725 0.430772 0.046 Uiso 1 1 calc R U . . .
O3 O 0.3599(3) 0.4078(3) 0.31868(7) 0.0244(5) Uani 1 1 d . . . . .
N1 N 0.1800(4) 0.6122(3) 0.42465(8) 0.0216(5) Uani 1 1 d . . . . .
H1A H 0.332292 0.624265 0.439822 0.026 Uiso 1 1 calc R U . . .
H1B H 0.074296 0.686656 0.444368 0.026 Uiso 1 1 calc R U . . .
C1 C 0.1842(5) 0.6740(4) 0.36457(10) 0.0252(6) Uani 1 1 d . . . . .
H1C H 0.348381 0.723388 0.354324 0.030 Uiso 1 1 calc R U . . .
H1D H 0.060933 0.775125 0.357826 0.030 Uiso 1 1 calc R U . . .
C2 C 0.1236(5) 0.4972(4) 0.33118(11) 0.0237(6) Uani 1 1 d . . . . .
H2A H 0.030208 0.528628 0.296503 0.028 Uiso 1 1 calc R U . . .
C3 C -0.0276(5) 0.3774(4) 0.37109(11) 0.0252(6) Uani 1 1 d . . . . .
H3A H -0.024849 0.241273 0.360212 0.030 Uiso 1 1 calc R U . . .
H3B H -0.200040 0.421884 0.372306 0.030 Uiso 1 1 calc R U . . .
C4 C 0.0988(5) 0.4076(4) 0.42697(11) 0.0212(6) Uani 1 1 d . . . . .
H4 H -0.021507 0.389413 0.457996 0.025 Uiso 1 1 calc R U . . .
C5 C 0.3240(5) 0.2841(3) 0.43669(11) 0.0214(6) Uani 1 1 d . . . . .
C6 C 0.3667(6) 0.2776(4) 0.27829(13) 0.0329(7) 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
F1 C6 1.334(4) . ?
F2 C6 1.329(3) . ?
F3 C6 1.332(4) . ?
O1 C5 1.203(3) . ?
O2 H2 0.8400 . ?
O2 C5 1.315(3) . ?
O3 C2 1.463(3) . ?
O3 C6 1.332(3) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 C1 1.506(3) . ?
N1 C4 1.503(3) . ?
C1 H1C 0.9900 . ?
C1 H1D 0.9900 . ?
C1 C2 1.513(4) . ?
C2 H2A 1.0000 . ?
C2 C3 1.517(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.522(4) . ?
C4 H4 1.0000 . ?
C4 C5 1.520(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
C5 O2 H2 109.5 . . ?
C6 O3 C2 117.9(2) . . ?
H1A N1 H1B 108.4 . . ?
C1 N1 H1A 110.0 . . ?
C1 N1 H1B 110.0 . . ?
C4 N1 H1A 110.0 . . ?
C4 N1 H1B 110.0 . . ?
C4 N1 C1 108.4(2) . . ?
N1 C1 H1C 110.6 . . ?
N1 C1 H1D 110.6 . . ?
N1 C1 C2 105.5(2) . . ?
H1C C1 H1D 108.8 . . ?
C2 C1 H1C 110.6 . . ?
C2 C1 H1D 110.6 . . ?
O3 C2 C1 105.5(2) . . ?
O3 C2 H2A 111.8 . . ?
O3 C2 C3 111.7(2) . . ?
C1 C2 H2A 111.8 . . ?
C1 C2 C3 103.8(2) . . ?
C3 C2 H2A 111.8 . . ?
C2 C3 H3A 111.1 . . ?
C2 C3 H3B 111.1 . . ?
C2 C3 C4 103.5(2) . . ?
H3A C3 H3B 109.0 . . ?
C4 C3 H3A 111.1 . . ?
C4 C3 H3B 111.1 . . ?
N1 C4 C3 103.5(2) . . ?
N1 C4 H4 110.0 . . ?
N1 C4 C5 108.2(2) . . ?
C3 C4 H4 110.0 . . ?
C5 C4 C3 114.9(2) . . ?
C5 C4 H4 110.0 . . ?
O1 C5 O2 125.3(3) . . ?
O1 C5 C4 122.9(2) . . ?
O2 C5 C4 111.8(2) . . ?
F2 C6 F1 107.4(3) . . ?
F2 C6 F3 107.9(3) . . ?
F2 C6 O3 107.8(2) . . ?
F3 C6 F1 105.6(3) . . ?
F3 C6 O3 114.1(2) . . ?
O3 C6 F1 113.7(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
O3 C2 C3 C4 74.3(3) . . . . ?
N1 C1 C2 O3 -90.9(2) . . . . ?
N1 C1 C2 C3 26.7(3) . . . . ?
N1 C4 C5 O1 18.0(3) . . . . ?
N1 C4 C5 O2 -163.3(2) . . . . ?
C1 N1 C4 C3 -19.5(3) . . . . ?
C1 N1 C4 C5 102.8(2) . . . . ?
C1 C2 C3 C4 -38.9(3) . . . . ?
C2 O3 C6 F1 50.8(3) . . . . ?
C2 O3 C6 F2 169.8(2) . . . . ?
C2 O3 C6 F3 -70.4(3) . . . . ?
C2 C3 C4 N1 35.8(3) . . . . ?
C2 C3 C4 C5 -81.9(3) . . . . ?
C3 C4 C5 O1 133.1(3) . . . . ?
C3 C4 C5 O2 -48.3(3) . . . . ?
C4 N1 C1 C2 -4.4(3) . . . . ?
C6 O3 C2 C1 -163.3(2) . . . . ?
C6 O3 C2 C3 84.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_vd404
_database_code_depnum_ccdc_archive 'CCDC 2361466'
loop_
_audit_author_name
_audit_author_address
'Svitlana Shishkina'
;SSI Institute for Single Crystals
Ukraine
;
_audit_update_record             
;
2024-06-09 deposited with the CCDC.	2024-06-24 downloaded from the CCDC.
;
_audit_creation_date             2024-06-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl, C6 H9 F3 N O3'
_chemical_formula_sum            'C6 H9 Cl F3 N O3'
_chemical_formula_weight         235.59
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
N N 0.0061 0.0033 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_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'

_cell_length_a                   8.3057(10)
_cell_length_b                   8.6418(8)
_cell_length_c                   13.3140(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     955.63(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1948
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      26.31
_cell_measurement_theta_min      2.89
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.919
_exptl_absorpt_coefficient_mu    0.429
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6475
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.989
_diffrn_reflns_theta_max         24.989
_diffrn_reflns_theta_min         2.810
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.684
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                1432
_reflns_number_total             1677
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Flack x determined using 465 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1677
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0485
_refine_ls_restrained_S_all      1.131
_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)+(0.0310P)²+0.0573P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0814
_refine_ls_wR_factor_ref         0.0848
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C3(H3A,H3B), C5(H5A,H5B)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.76272(13) 0.76357(11) 0.62758(7) 0.0265(3) Uani 1 1 d . . . . .
F1 F 0.5432(4) 0.2315(3) 0.4200(2) 0.0582(9) Uani 1 1 d . . . . .
F2 F 0.4228(4) 0.3780(3) 0.5263(2) 0.0576(9) Uani 1 1 d . . . . .
F3 F 0.6674(4) 0.3114(3) 0.54935(19) 0.0539(9) Uani 1 1 d . . . . .
O1 O 0.9279(4) 0.9291(4) 0.2723(2) 0.0448(9) Uani 1 1 d . . . . .
O2 O 0.6661(4) 0.9455(4) 0.2394(3) 0.0477(10) Uani 1 1 d . . . . .
H2 H 0.691698 1.028650 0.210837 0.072 Uiso 1 1 calc R U . . .
O3 O 0.6006(4) 0.4822(3) 0.4311(2) 0.0293(8) Uani 1 1 d . . . . .
N1 N 0.8849(4) 0.7083(3) 0.4157(2) 0.0227(9) Uani 1 1 d . . . . .
H1A H 0.979314 0.743419 0.389540 0.027 Uiso 1 1 calc R U . . .
H1B H 0.870337 0.752708 0.476950 0.027 Uiso 1 1 calc R U . . .
C2 C 0.7471(5) 0.7493(4) 0.3470(3) 0.0223(9) Uani 1 1 d . . . . .
H2A H 0.649530 0.774941 0.387692 0.027 Uiso 1 1 calc R U . . .
C3 C 0.7187(6) 0.5993(5) 0.2885(3) 0.0289(12) Uani 1 1 d . . . . .
H3A H 0.608000 0.595045 0.261056 0.035 Uiso 1 1 calc R U . . .
H3B H 0.796840 0.588017 0.232886 0.035 Uiso 1 1 calc R U . . .
C4 C 0.7441(6) 0.4777(4) 0.3676(3) 0.0264(10) Uani 1 1 d . . . . .
H4 H 0.762348 0.372922 0.337857 0.032 Uiso 1 1 calc R U . . .
C5 C 0.8896(6) 0.5351(4) 0.4257(3) 0.0265(11) Uani 1 1 d . . . . .
H5A H 0.882627 0.504036 0.497110 0.032 Uiso 1 1 calc R U . . .
H5B H 0.990242 0.492938 0.396773 0.032 Uiso 1 1 calc R U . . .
C6 C 0.7926(6) 0.8859(6) 0.2825(3) 0.0269(11) Uani 1 1 d . . . . .
C7 C 0.5615(7) 0.3543(6) 0.4793(4) 0.0374(12) 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
F1 C7 1.332(5) . ?
F2 C7 1.327(6) . ?
F3 C7 1.335(6) . ?
O1 C6 1.192(6) . ?
O2 H2 0.8400 . ?
O2 C6 1.304(5) . ?
O3 C4 1.461(5) . ?
O3 C7 1.318(5) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 C2 1.507(5) . ?
N1 C5 1.503(5) . ?
C2 H2A 1.0000 . ?
C2 C3 1.530(5) . ?
C2 C6 1.508(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.503(5) . ?
C4 H4 1.0000 . ?
C4 C5 1.518(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?

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 O2 H2 109.5 . . ?
C7 O3 C4 117.4(3) . . ?
H1A N1 H1B 108.4 . . ?
C2 N1 H1A 110.1 . . ?
C2 N1 H1B 110.1 . . ?
C5 N1 H1A 110.1 . . ?
C5 N1 H1B 110.1 . . ?
C5 N1 C2 107.9(3) . . ?
N1 C2 H2A 109.8 . . ?
N1 C2 C3 103.1(3) . . ?
N1 C2 C6 109.8(3) . . ?
C3 C2 H2A 109.8 . . ?
C6 C2 H2A 109.8 . . ?
C6 C2 C3 114.4(3) . . ?
C2 C3 H3A 111.3 . . ?
C2 C3 H3B 111.3 . . ?
H3A C3 H3B 109.2 . . ?
C4 C3 C2 102.4(3) . . ?
C4 C3 H3A 111.3 . . ?
C4 C3 H3B 111.3 . . ?
O3 C4 C3 105.8(4) . . ?
O3 C4 H4 112.2 . . ?
O3 C4 C5 110.2(3) . . ?
C3 C4 H4 112.2 . . ?
C3 C4 C5 103.9(3) . . ?
C5 C4 H4 112.2 . . ?
N1 C5 C4 105.1(3) . . ?
N1 C5 H5A 110.7 . . ?
N1 C5 H5B 110.7 . . ?
C4 C5 H5A 110.7 . . ?
C4 C5 H5B 110.7 . . ?
H5A C5 H5B 108.8 . . ?
O1 C6 O2 125.9(4) . . ?
O1 C6 C2 123.1(4) . . ?
O2 C6 C2 111.0(4) . . ?
F1 C7 F3 105.6(4) . . ?
F2 C7 F1 107.6(4) . . ?
F2 C7 F3 106.6(4) . . ?
O3 C7 F1 114.1(4) . . ?
O3 C7 F2 108.3(4) . . ?
O3 C7 F3 114.3(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
O3 C4 C5 N1 -84.5(3) . . . . ?
N1 C2 C3 C4 38.5(4) . . . . ?
N1 C2 C6 O1 15.7(6) . . . . ?
N1 C2 C6 O2 -165.6(3) . . . . ?
C2 N1 C5 C4 -4.1(4) . . . . ?
C2 C3 C4 O3 74.6(4) . . . . ?
C2 C3 C4 C5 -41.5(4) . . . . ?
C3 C2 C6 O1 -99.6(5) . . . . ?
C3 C2 C6 O2 79.1(5) . . . . ?
C3 C4 C5 N1 28.4(4) . . . . ?
C4 O3 C7 F1 -55.5(6) . . . . ?
C4 O3 C7 F2 -175.4(4) . . . . ?
C4 O3 C7 F3 66.0(5) . . . . ?
C5 N1 C2 C3 -21.2(4) . . . . ?
C5 N1 C2 C6 -143.5(3) . . . . ?
C6 C2 C3 C4 157.6(4) . . . . ?
C7 O3 C4 C3 153.9(4) . . . . ?
C7 O3 C4 C5 -94.4(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_v387
_database_code_depnum_ccdc_archive 'CCDC 2358276'
loop_
_audit_author_name
_audit_author_address
'Svitlana Shishkina'
;SSI Institute for Single Crystals
Ukraine
;
_audit_update_record             
;
2024-05-26 deposited with the CCDC.	2024-06-24 downloaded from the CCDC.
;
_audit_creation_date             2024-05-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl, C6 H9 F3 N O3'
_chemical_formula_sum            'C6 H9 Cl F3 N O3'
_chemical_formula_weight         235.59
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
N N 0.0061 0.0033 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_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'

_cell_length_a                   8.3231(7)
_cell_length_b                   8.6507(7)
_cell_length_c                   13.3347(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     960.11(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2125
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      24.24
_cell_measurement_theta_min      2.88
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.920
_exptl_absorpt_coefficient_mu    0.427
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6951
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.807
_diffrn_ambient_temperature      172.65
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1518
_reflns_number_total             1691
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 576 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1691
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0316
_refine_ls_restrained_S_all      1.080
_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)+(0.0361P)²+0.0815P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0700
_refine_ls_wR_factor_ref         0.0730
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C3(H3A,H3B), C5(H5A,H5B)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.76281(8) 0.76334(9) 0.37240(6) 0.0281(2) Uani 1 1 d . . . . .
F1 F 0.4231(3) 0.3776(3) 0.47417(19) 0.0605(7) Uani 1 1 d . . . . .
F2 F 0.5432(3) 0.2310(3) 0.57995(18) 0.0608(7) Uani 1 1 d . . . . .
F3 F 0.6678(3) 0.3117(3) 0.45071(17) 0.0566(7) Uani 1 1 d . . . . .
O1 O 0.9285(3) 0.9294(3) 0.7278(2) 0.0473(7) Uani 1 1 d . . . . .
O2 O 0.6661(3) 0.9457(3) 0.7612(2) 0.0496(8) Uani 1 1 d . . . . .
H2 H 0.692237 1.028483 0.789819 0.074 Uiso 1 1 calc R U . . .
O3 O 0.6007(2) 0.4816(2) 0.56898(18) 0.0325(6) Uani 1 1 d . . . . .
N1 N 0.8845(3) 0.7082(3) 0.58448(19) 0.0260(6) Uani 1 1 d . . . . .
H1A H 0.978881 0.743185 0.610410 0.031 Uiso 1 1 calc R U . . .
H1B H 0.869599 0.753005 0.523438 0.031 Uiso 1 1 calc R U . . .
C2 C 0.7480(3) 0.7488(3) 0.6533(2) 0.0251(7) Uani 1 1 d . . . . .
H2A H 0.650414 0.774153 0.612672 0.030 Uiso 1 1 calc R U . . .
C3 C 0.7193(4) 0.5994(4) 0.7119(3) 0.0330(9) Uani 1 1 d . . . . .
H3A H 0.797345 0.588090 0.767381 0.040 Uiso 1 1 calc R U . . .
H3B H 0.608856 0.595478 0.739360 0.040 Uiso 1 1 calc R U . . .
C4 C 0.7443(4) 0.4772(3) 0.6326(2) 0.0292(7) Uani 1 1 d . . . . .
H4 H 0.762840 0.372545 0.662297 0.035 Uiso 1 1 calc R U . . .
C5 C 0.8893(4) 0.5349(3) 0.5739(3) 0.0294(8) Uani 1 1 d . . . . .
H5A H 0.990155 0.492609 0.602159 0.035 Uiso 1 1 calc R U . . .
H5B H 0.881534 0.504291 0.502504 0.035 Uiso 1 1 calc R U . . .
C6 C 0.7920(4) 0.8853(4) 0.7179(3) 0.0295(8) Uani 1 1 d . . . . .
C7 C 0.5610(5) 0.3543(4) 0.5203(3) 0.0383(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
F1 C7 1.318(5) . ?
F2 C7 1.338(4) . ?
F3 C7 1.337(4) . ?
O1 C6 1.206(4) . ?
O2 H2 0.8400 . ?
O2 C6 1.306(4) . ?
O3 C4 1.466(4) . ?
O3 C7 1.320(4) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 C2 1.502(4) . ?
N1 C5 1.506(4) . ?
C2 H2A 1.0000 . ?
C2 C3 1.529(4) . ?
C2 C6 1.508(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.509(4) . ?
C4 H4 1.0000 . ?
C4 C5 1.523(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?

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 O2 H2 109.5 . . ?
C7 O3 C4 117.8(2) . . ?
H1A N1 H1B 108.4 . . ?
C2 N1 H1A 110.1 . . ?
C2 N1 H1B 110.1 . . ?
C2 N1 C5 108.1(2) . . ?
C5 N1 H1A 110.1 . . ?
C5 N1 H1B 110.1 . . ?
N1 C2 H2A 109.6 . . ?
N1 C2 C3 103.5(2) . . ?
N1 C2 C6 110.4(2) . . ?
C3 C2 H2A 109.6 . . ?
C6 C2 H2A 109.6 . . ?
C6 C2 C3 114.1(3) . . ?
C2 C3 H3A 111.3 . . ?
C2 C3 H3B 111.3 . . ?
H3A C3 H3B 109.2 . . ?
C4 C3 C2 102.3(2) . . ?
C4 C3 H3A 111.3 . . ?
C4 C3 H3B 111.3 . . ?
O3 C4 C3 105.9(3) . . ?
O3 C4 H4 112.2 . . ?
O3 C4 C5 109.9(3) . . ?
C3 C4 H4 112.2 . . ?
C3 C4 C5 103.9(3) . . ?
C5 C4 H4 112.2 . . ?
N1 C5 C4 104.9(2) . . ?
N1 C5 H5A 110.8 . . ?
N1 C5 H5B 110.8 . . ?
C4 C5 H5A 110.8 . . ?
C4 C5 H5B 110.8 . . ?
H5A C5 H5B 108.8 . . ?
O1 C6 O2 125.6(3) . . ?
O1 C6 C2 122.6(3) . . ?
O2 C6 C2 111.8(3) . . ?
F1 C7 F2 107.6(3) . . ?
F1 C7 F3 107.3(3) . . ?
F1 C7 O3 108.7(3) . . ?
F3 C7 F2 105.4(3) . . ?
O3 C7 F2 113.6(3) . . ?
O3 C7 F3 113.9(3) . . ?

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
O3 C4 C5 N1 84.9(3) . . . . ?
N1 C2 C3 C4 -38.3(3) . . . . ?
N1 C2 C6 O1 -15.5(5) . . . . ?
N1 C2 C6 O2 165.2(3) . . . . ?
C2 N1 C5 C4 3.9(3) . . . . ?
C2 C3 C4 O3 -74.6(3) . . . . ?
C2 C3 C4 C5 41.1(3) . . . . ?
C3 C2 C6 O1 100.4(4) . . . . ?
C3 C2 C6 O2 -78.8(4) . . . . ?
C3 C4 C5 N1 -28.0(3) . . . . ?
C4 O3 C7 F1 175.1(3) . . . . ?
C4 O3 C7 F2 55.3(4) . . . . ?
C4 O3 C7 F3 -65.4(4) . . . . ?
C5 N1 C2 C3 21.3(3) . . . . ?
C5 N1 C2 C6 143.8(3) . . . . ?
C6 C2 C3 C4 -158.3(3) . . . . ?
C7 O3 C4 C3 -154.2(3) . . . . ?
C7 O3 C4 C5 94.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
