data_y
_audit_creation_date               2022-06-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2014/7'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C9 H6 Cl F3 O'
_chemical_formula_sum              'C9 H6 Cl F3 O'
_chemical_formula_weight           222.59
_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'
 '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             61
_space_group_name_H-M_alt          'P b c a'
_space_group_name_Hall             '-P 2ac 2ab'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 'x+1/2, -y+1/2, -z'
 '-x, y+1/2, -z+1/2'
 '-x+1/2, -y, z+1/2'
 '-x, -y, -z'
 '-x-1/2, y-1/2, z'
 'x, -y-1/2, z-1/2'
 'x-1/2, y, -z-1/2'

_cell_length_a                     15.120(3)
_cell_length_b                     5.9966(13)
_cell_length_c                     20.980(4)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       1902.3(7)
_cell_formula_units_Z              8
_cell_measurement_reflns_used      6587
_cell_measurement_temperature      296(2)
_cell_measurement_theta_max        31.29
_cell_measurement_theta_min        2.36
_shelx_estimated_absorpt_T_max     0.960
_shelx_estimated_absorpt_T_min     0.941
_exptl_absorpt_coefficient_mu      0.409
_exptl_absorpt_correction_T_max    0.7463
_exptl_absorpt_correction_T_min    0.5605
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details    
 'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1292 before and 0.0663 after correction. The Ratio of minimum to maximum transmission is 0.7510. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              ?
_exptl_crystal_density_diffrn      1.554
_exptl_crystal_density_meas        .
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               896
_exptl_crystal_size_max            0.15
_exptl_crystal_size_mid            0.12
_exptl_crystal_size_min            0.1
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0379
_diffrn_reflns_av_unetI/netI       0.0281
_diffrn_reflns_Laue_measured_fraction_full  0.996
_diffrn_reflns_Laue_measured_fraction_max  0.996
_diffrn_reflns_limit_h_max         18
_diffrn_reflns_limit_h_min         -18
_diffrn_reflns_limit_k_max         7
_diffrn_reflns_limit_k_min         -7
_diffrn_reflns_limit_l_max         23
_diffrn_reflns_limit_l_min         -25
_diffrn_reflns_number              12735
_diffrn_reflns_point_group_measured_fraction_full  0.996
_diffrn_reflns_point_group_measured_fraction_max  0.996
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           25.991
_diffrn_reflns_theta_min           1.941
_diffrn_ambient_temperature        296.15
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.996
_diffrn_measured_fraction_theta_max  0.996
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_monochromator    'graphite'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  1527
_reflns_number_total               1861
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'XL (Sheldrick, 2008)'
_computing_structure_solution      'XM (Sheldrick, 2008)'
_refine_diff_density_max           0.325
_refine_diff_density_min           -0.242
_refine_diff_density_rms           0.073
_refine_ls_extinction_coef         0.057(4)
_refine_ls_extinction_expression  
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_extinction_method       'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref     1.067
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       128
_refine_ls_number_reflns           1861
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0638
_refine_ls_R_factor_gt             0.0534
_refine_ls_restrained_S_all        1.067
_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)+(0.0594P)²+1.1406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1325
_refine_ls_wR_factor_ref           0.1467
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
_atom_sites_special_details
;
The structure was solved using Direct Methods (ShelXS). RE = 0.3, Nqual =  -1, Ralpha = 0.055
;
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 0.63437(13) 0.6052(4) 0.42515(11) 0.0490(5) Uani 1 1 d . . . . .
 C2 C 0.59472(15) 0.3979(4) 0.42314(13) 0.0582(6) Uani 1 1 d . . . . .
 H2 H 0.5751 0.3414 0.3844 0.070 Uiso 1 1 calc R . . . .
 C3 C 0.58394(17) 0.2741(5) 0.47774(14) 0.0664(7) Uani 1 1 d . . . . .
 H3 H 0.5571 0.1346 0.4760 0.080 Uiso 1 1 calc R . . . .
 C4 C 0.61317(17) 0.3585(5) 0.53478(13) 0.0644(7) Uani 1 1 d . . . . .
 C5 C 0.65294(17) 0.5645(5) 0.53873(12) 0.0674(7) Uani 1 1 d . . . . .
 H5 H 0.6723 0.6197 0.5778 0.081 Uiso 1 1 calc R . . . .
 C6 C 0.66357(15) 0.6876(4) 0.48372(12) 0.0587(6) Uani 1 1 d . . . . .
 H6 H 0.6905 0.8269 0.4857 0.070 Uiso 1 1 calc R . . . .
 C7 C 0.64894(14) 0.7439(4) 0.36714(12) 0.0534(6) Uani 1 1 d . . . . .
 C8 C 0.61765(18) 0.6535(5) 0.30410(12) 0.0658(7) Uani 1 1 d . . . . .
 H8A H 0.6512 0.5199 0.2943 0.079 Uiso 1 1 calc R . . . .
 H8B H 0.5561 0.6106 0.3082 0.079 Uiso 1 1 calc R . . . .
 C9 C 0.6260(2) 0.8119(6) 0.24946(14) 0.0795(8) Uani 1 1 d . . . . .
 Cl1 Cl 0.60134(7) 0.19845(18) 0.60321(4) 0.1006(4) Uani 1 1 d . . . . .
 F1 F 0.70890(14) 0.8608(4) 0.23556(10) 0.1083(7) Uani 1 1 d . . . . .
 F2 F 0.59102(19) 0.7270(5) 0.19654(9) 0.1333(10) Uani 1 1 d . . . . .
 F3 F 0.58461(16) 1.0024(4) 0.25895(11) 0.1238(9) Uani 1 1 d . . . . .
 O1 O 0.68487(14) 0.9244(3) 0.37013(10) 0.0778(6) 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 C2 1.381(3) . ?
 C1 C6 1.396(3) . ?
 C1 C7 1.490(3) . ?
 C2 H2 0.9300 . ?
 C2 C3 1.375(4) . ?
 C3 H3 0.9300 . ?
 C3 C4 1.372(4) . ?
 C4 C5 1.377(4) . ?
 C4 Cl1 1.736(3) . ?
 C5 H5 0.9300 . ?
 C5 C6 1.379(4) . ?
 C6 H6 0.9300 . ?
 C7 C8 1.506(3) . ?
 C7 O1 1.212(3) . ?
 C8 H8A 0.9700 . ?
 C8 H8B 0.9700 . ?
 C8 C9 1.494(4) . ?
 C9 F1 1.319(4) . ?
 C9 F2 1.331(4) . ?
 C9 F3 1.318(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
 C2 C1 C6 118.9(2) . . ?
 C2 C1 C7 122.8(2) . . ?
 C6 C1 C7 118.3(2) . . ?
 C1 C2 H2 119.6 . . ?
 C3 C2 C1 120.8(2) . . ?
 C3 C2 H2 119.6 . . ?
 C2 C3 H3 120.4 . . ?
 C4 C3 C2 119.3(2) . . ?
 C4 C3 H3 120.4 . . ?
 C3 C4 C5 121.6(3) . . ?
 C3 C4 Cl1 119.0(2) . . ?
 C5 C4 Cl1 119.4(2) . . ?
 C4 C5 H5 120.6 . . ?
 C4 C5 C6 118.7(2) . . ?
 C6 C5 H5 120.6 . . ?
 C1 C6 H6 119.7 . . ?
 C5 C6 C1 120.7(2) . . ?
 C5 C6 H6 119.7 . . ?
 C1 C7 C8 118.0(2) . . ?
 O1 C7 C1 121.5(2) . . ?
 O1 C7 C8 120.5(2) . . ?
 C7 C8 H8A 108.6 . . ?
 C7 C8 H8B 108.6 . . ?
 H8A C8 H8B 107.6 . . ?
 C9 C8 C7 114.7(2) . . ?
 C9 C8 H8A 108.6 . . ?
 C9 C8 H8B 108.6 . . ?
 F1 C9 C8 113.0(3) . . ?
 F1 C9 F2 106.1(3) . . ?
 F2 C9 C8 111.3(3) . . ?
 F3 C9 C8 113.3(3) . . ?
 F3 C9 F1 107.0(3) . . ?
 F3 C9 F2 105.6(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
 C1 C2 C3 C4 -0.1(4) . . . . ?
 C1 C7 C8 C9 173.9(2) . . . . ?
 C2 C1 C6 C5 -0.1(3) . . . . ?
 C2 C1 C7 C8 0.9(3) . . . . ?
 C2 C1 C7 O1 -179.1(2) . . . . ?
 C2 C3 C4 C5 0.1(4) . . . . ?
 C2 C3 C4 Cl1 -178.68(18) . . . . ?
 C3 C4 C5 C6 -0.2(4) . . . . ?
 C4 C5 C6 C1 0.2(4) . . . . ?
 C6 C1 C2 C3 0.1(3) . . . . ?
 C6 C1 C7 C8 179.7(2) . . . . ?
 C6 C1 C7 O1 -0.3(3) . . . . ?
 C7 C1 C2 C3 178.9(2) . . . . ?
 C7 C1 C6 C5 -179.0(2) . . . . ?
 C7 C8 C9 F1 65.4(3) . . . . ?
 C7 C8 C9 F2 -175.3(3) . . . . ?
 C7 C8 C9 F3 -56.5(4) . . . . ?
 Cl1 C4 C5 C6 178.61(18) . . . . ?
 O1 C7 C8 C9 -6.1(4) . . . . ?


_olex2_submission_special_instructions  'No special instructions were received'
