data_cxy3230_0m_4
_audit_creation_date               2021-03-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number       '2018/3'
_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. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C11 H10 F N O3'
_chemical_formula_sum              'C11 H10 F N O3'
_chemical_formula_weight           223.20
_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' 0.0181 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'
 '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'

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

_cell_length_a                     4.9616(4)
_cell_length_b                     8.3141(7)
_cell_length_c                     25.024(2)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       1032.27(15)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      9528
_cell_measurement_temperature      100.0
_cell_measurement_theta_max        72.03
_cell_measurement_theta_min        3.53
_shelx_estimated_absorpt_T_max     0.810
_shelx_estimated_absorpt_T_min     0.747
_exptl_absorpt_coefficient_mu      0.999
_exptl_absorpt_correction_T_max    ?
_exptl_absorpt_correction_T_min    ?
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 43270 reflections, Rint = 0.1126
 (35202 with I > 3sig(I), Rint = 0.1093)
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.436
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               464
_exptl_crystal_size_max            0.31
_exptl_crystal_size_mid            0.25
_exptl_crystal_size_min            0.22
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.087
_diffrn_reflns_av_unetI/netI       0.0282
_diffrn_reflns_Laue_measured_fraction_full  1.000
_diffrn_reflns_Laue_measured_fraction_max  0.999
_diffrn_reflns_limit_h_max         ?
_diffrn_reflns_limit_h_min         ?
_diffrn_reflns_limit_k_max         ?
_diffrn_reflns_limit_k_min         ?
_diffrn_reflns_limit_l_max         ?
_diffrn_reflns_limit_l_min         ?
_diffrn_reflns_number              2020
_diffrn_reflns_point_group_measured_fraction_full  0.999
_diffrn_reflns_point_group_measured_fraction_max  0.999
_diffrn_reflns_theta_full          67.679
_diffrn_reflns_theta_max           72.119
_diffrn_reflns_theta_min           3.532
_diffrn_ambient_temperature        100.0
_diffrn_detector                   'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean   7.9
_diffrn_detector_type              'CMOS area detector'
_diffrn_measured_fraction_theta_full  1.000
_diffrn_measured_fraction_theta_max  0.999
_diffrn_measurement_device         'three-circle diffractometer'
_diffrn_measurement_device_type    'Bruker D8 VENTURE'
_diffrn_measurement_method         'ω and φ scans'
_diffrn_radiation_monochromator    'mirror optics'
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54178
_diffrn_source                     'microfocus sealed X-ray tube'
_diffrn_source_current             1.1
_diffrn_source_power               0.055
_diffrn_source_type                'Incoatec I\ms'
_diffrn_source_voltage             50.0
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.653
_reflns_Friedel_fraction_full      0.999
_reflns_Friedel_fraction_max       0.999
_reflns_number_gt                  1990
_reflns_number_total               2020
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics      'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max           0.306
_refine_diff_density_min           -0.243
_refine_diff_density_rms           0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 778 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     0.11(17)
_refine_ls_extinction_coef         0.014(3)
_refine_ls_extinction_expression  
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_extinction_method       'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref     1.185
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       152
_refine_ls_number_reflns           2020
_refine_ls_number_restraints       1
_refine_ls_R_factor_all            0.0527
_refine_ls_R_factor_gt             0.0524
_refine_ls_restrained_S_all        1.192
_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)+(0.0917P)²+0.4887P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1579
_refine_ls_wR_factor_ref           0.1582
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 F1A-C11 \\sim F1-C3
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F1) = Uanis(F1A)
4. Others
 Sof(H3)=Sof(F1A)=1-FVAR(1)
 Sof(F1)=Sof(H11)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C5(H5), C9(H9)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3), C10(H10), C11(H11)
5.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
5.d 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
 F1 F 0.5263(5) 0.2981(3) 0.69280(8) 0.0394(7) Uani 0.953(5) 1 d D . P A 1
 O1 O 0.3214(5) 0.4959(3) 0.51780(9) 0.0358(6) Uani 1 1 d . . . . .
 O2 O 0.4167(5) 0.1534(3) 0.53523(9) 0.0320(6) Uani 1 1 d . . . . .
 H2 H 0.548994 0.127326 0.516152 0.048 Uiso 1 1 calc R U . . .
 O3 O 1.0307(5) 0.4917(3) 0.63320(9) 0.0350(6) Uani 1 1 d . . . . .
 N1 N 0.6753(7) 0.5319(3) 0.57530(11) 0.0321(7) Uani 1 1 d . . . . .
 C1 C 0.9084(8) -0.0544(5) 0.72818(15) 0.0415(9) Uani 1 1 d . . . . .
 H1 H 0.933643 -0.125259 0.757541 0.050 Uiso 1 1 calc R U . . .
 C2 C 0.7282(9) 0.0722(5) 0.73240(13) 0.0397(9) Uani 1 1 d . . . . .
 H2A H 0.630024 0.089869 0.764453 0.048 Uiso 1 1 calc R U . . .
 C3 C 0.6951(8) 0.1719(4) 0.68895(13) 0.0330(8) Uani 1 1 d D . . . .
 H3 H 0.572986 0.259418 0.691975 0.040 Uiso 0.047(5) 1 calc R U P A 2
 C4 C 0.8309(7) 0.1512(4) 0.64099(12) 0.0293(7) Uani 1 1 d . . . . .
 C5 C 0.7856(7) 0.2621(4) 0.59429(12) 0.0287(7) Uani 1 1 d . . . . .
 H5 H 0.905654 0.225317 0.564597 0.034 Uiso 1 1 calc R U . . .
 C6 C 0.8513(7) 0.4386(4) 0.60527(12) 0.0303(7) Uani 1 1 d . . . . .
 C7 C 0.6957(10) 0.7067(5) 0.57118(17) 0.0474(10) Uani 1 1 d . . . . .
 H7A H 0.521826 0.751024 0.559859 0.071 Uiso 1 1 calc R U . . .
 H7B H 0.834191 0.734812 0.544857 0.071 Uiso 1 1 calc R U . . .
 H7C H 0.744872 0.751613 0.606054 0.071 Uiso 1 1 calc R U . . .
 C8 C 0.4811(7) 0.4430(4) 0.55012(12) 0.0311(7) Uani 1 1 d . . . . .
 C9 C 0.4961(7) 0.2720(4) 0.57187(13) 0.0305(8) Uani 1 1 d . . . . .
 H9 H 0.370017 0.265705 0.602983 0.037 Uiso 1 1 calc R U . . .
 C10 C 1.0515(8) -0.0782(5) 0.68151(15) 0.0411(9) Uani 1 1 d . . . . .
 H10 H 1.176915 -0.164202 0.679069 0.049 Uiso 1 1 calc R U . . .
 C11 C 1.0125(8) 0.0233(4) 0.63816(13) 0.0341(8) Uani 1 1 d D . . . .
 H11 H 1.110748 0.005445 0.606126 0.041 Uiso 0.953(5) 1 calc R U P A 1
 F1A F 1.200(7) -0.005(6) 0.6063(15) 0.0394(7) Uani 0.047(5) 1 d D . P A 2


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 F1 C3 1.346(4) . ?
 O1 C8 1.215(4) . ?
 O2 H2 0.8400 . ?
 O2 C9 1.403(4) . ?
 O3 C6 1.215(4) . ?
 N1 C6 1.388(5) . ?
 N1 C7 1.460(5) . ?
 N1 C8 1.369(5) . ?
 C1 H1 0.9500 . ?
 C1 C2 1.385(6) . ?
 C1 C10 1.381(6) . ?
 C2 H2A 0.9500 . ?
 C2 C3 1.377(5) . ?
 C3 H3 0.9500 . ?
 C3 C4 1.387(5) . ?
 C4 C5 1.506(4) . ?
 C4 C11 1.395(5) . ?
 C5 H5 1.0000 . ?
 C5 C6 1.528(5) . ?
 C5 C9 1.544(5) . ?
 C7 H7A 0.9800 . ?
 C7 H7B 0.9800 . ?
 C7 H7C 0.9800 . ?
 C8 C9 1.524(5) . ?
 C9 H9 1.0000 . ?
 C10 H10 0.9500 . ?
 C10 C11 1.388(5) . ?
 C11 H11 0.9500 . ?
 C11 F1A 1.25(2) . ?

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
 C9 O2 H2 109.5 . . ?
 C6 N1 C7 123.4(3) . . ?
 C8 N1 C6 112.9(3) . . ?
 C8 N1 C7 123.6(3) . . ?
 C2 C1 H1 119.8 . . ?
 C10 C1 H1 119.8 . . ?
 C10 C1 C2 120.3(3) . . ?
 C1 C2 H2A 120.8 . . ?
 C3 C2 C1 118.3(3) . . ?
 C3 C2 H2A 120.8 . . ?
 F1 C3 C2 119.1(3) . . ?
 F1 C3 C4 117.5(3) . . ?
 C2 C3 H3 118.3 . . ?
 C2 C3 C4 123.4(3) . . ?
 C4 C3 H3 118.3 . . ?
 C3 C4 C5 121.5(3) . . ?
 C3 C4 C11 116.9(3) . . ?
 C11 C4 C5 121.6(3) . . ?
 C4 C5 H5 107.5 . . ?
 C4 C5 C6 114.6(3) . . ?
 C4 C5 C9 116.9(3) . . ?
 C6 C5 H5 107.5 . . ?
 C6 C5 C9 102.3(3) . . ?
 C9 C5 H5 107.5 . . ?
 O3 C6 N1 124.6(3) . . ?
 O3 C6 C5 127.5(3) . . ?
 N1 C6 C5 107.8(3) . . ?
 N1 C7 H7A 109.5 . . ?
 N1 C7 H7B 109.5 . . ?
 N1 C7 H7C 109.5 . . ?
 H7A C7 H7B 109.5 . . ?
 H7A C7 H7C 109.5 . . ?
 H7B C7 H7C 109.5 . . ?
 O1 C8 N1 124.8(3) . . ?
 O1 C8 C9 127.4(3) . . ?
 N1 C8 C9 107.8(3) . . ?
 O2 C9 C5 117.4(3) . . ?
 O2 C9 C8 114.1(3) . . ?
 O2 C9 H9 107.2 . . ?
 C5 C9 H9 107.2 . . ?
 C8 C9 C5 103.0(3) . . ?
 C8 C9 H9 107.2 . . ?
 C1 C10 H10 119.9 . . ?
 C1 C10 C11 120.2(4) . . ?
 C11 C10 H10 119.9 . . ?
 C4 C11 H11 119.5 . . ?
 C10 C11 C4 120.9(3) . . ?
 C10 C11 H11 119.5 . . ?
 F1A C11 C4 131(2) . . ?
 F1A C11 C10 106(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
 F1 C3 C4 C5 -1.8(5) . . . . ?
 F1 C3 C4 C11 177.8(3) . . . . ?
 O1 C8 C9 O2 32.4(5) . . . . ?
 O1 C8 C9 C5 160.9(3) . . . . ?
 N1 C8 C9 O2 -150.1(3) . . . . ?
 N1 C8 C9 C5 -21.7(3) . . . . ?
 C1 C2 C3 F1 -178.2(3) . . . . ?
 C1 C2 C3 C4 0.7(6) . . . . ?
 C1 C10 C11 C4 0.5(6) . . . . ?
 C1 C10 C11 F1A 167(2) . . . . ?
 C2 C1 C10 C11 -1.0(6) . . . . ?
 C2 C3 C4 C5 179.2(3) . . . . ?
 C2 C3 C4 C11 -1.1(5) . . . . ?
 C3 C4 C5 C6 59.8(4) . . . . ?
 C3 C4 C5 C9 -59.9(4) . . . . ?
 C3 C4 C11 C10 0.5(5) . . . . ?
 C3 C4 C11 F1A -163(3) . . . . ?
 C4 C5 C6 O3 35.5(5) . . . . ?
 C4 C5 C6 N1 -147.3(3) . . . . ?
 C4 C5 C9 O2 -83.4(4) . . . . ?
 C4 C5 C9 C8 150.2(3) . . . . ?
 C5 C4 C11 C10 -179.8(3) . . . . ?
 C5 C4 C11 F1A 17(3) . . . . ?
 C6 N1 C8 O1 -172.6(3) . . . . ?
 C6 N1 C8 C9 9.9(4) . . . . ?
 C6 C5 C9 O2 150.5(3) . . . . ?
 C6 C5 C9 C8 24.2(3) . . . . ?
 C7 N1 C6 O3 4.0(5) . . . . ?
 C7 N1 C6 C5 -173.3(3) . . . . ?
 C7 N1 C8 O1 7.4(6) . . . . ?
 C7 N1 C8 C9 -170.1(3) . . . . ?
 C8 N1 C6 O3 -176.0(3) . . . . ?
 C8 N1 C6 C5 6.7(4) . . . . ?
 C9 C5 C6 O3 163.1(3) . . . . ?
 C9 C5 C6 N1 -19.7(3) . . . . ?
 C10 C1 C2 C3 0.5(6) . . . . ?
 C11 C4 C5 C6 -119.8(4) . . . . ?
 C11 C4 C5 C9 120.5(4) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
