data_tz_ac
_audit_creation_date               2025-06-25
_audit_creation_method
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number       '2019/3'
_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         
 (5-(4-fluorophenyl)-3-hydroxy-1H-pyrrol-2-yl)(phenyl)methanone
_chemical_formula_moiety           'C17 H12 F N O2'
_chemical_formula_sum              'C17 H12 F N O2'
_chemical_formula_weight           281.28
_chemical_melting_point            ?
_chemical_oxdiff_formula           'C17 H12 F N O2'
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'

_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        'monoclinic'
_space_group_IT_number             14
_space_group_name_H-M_alt          'P 1 21/c 1'
_space_group_name_Hall             '-P 2ybc'
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                     13.0439(3)
_cell_length_b                     11.4099(3)
_cell_length_c                     8.9076(2)
_cell_angle_alpha                  90
_cell_angle_beta                   93.294(2)
_cell_angle_gamma                  90
_cell_volume                       1323.52(6)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      4207
_cell_measurement_temperature      100.01(10)
_cell_measurement_theta_max        76.0720
_cell_measurement_theta_min        4.9350
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      0.851
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.60577
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear yellow'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_modifier     .
_exptl_crystal_colour_primary      yellow
_exptl_crystal_density_diffrn      1.412
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         prism
_exptl_crystal_F_000               584
_exptl_crystal_preparation         'Recrystallization from toluene'
_exptl_crystal_recrystallization_method  ?
_exptl_crystal_size_max            0.34
_exptl_crystal_size_mid            0.28
_exptl_crystal_size_min            0.22
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0206
_diffrn_reflns_av_unetI/netI       0.0221
_diffrn_reflns_Laue_measured_fraction_full  1.000
_diffrn_reflns_Laue_measured_fraction_max  0.993
_diffrn_reflns_limit_h_max         11
_diffrn_reflns_limit_h_min         -16
_diffrn_reflns_limit_k_max         14
_diffrn_reflns_limit_k_min         -12
_diffrn_reflns_limit_l_max         10
_diffrn_reflns_limit_l_min         -11
_diffrn_reflns_number              4999
_diffrn_reflns_point_group_measured_fraction_full  1.000
_diffrn_reflns_point_group_measured_fraction_max  0.993
_diffrn_reflns_theta_full          67.684
_diffrn_reflns_theta_max           72.484
_diffrn_reflns_theta_min           3.394
_diffrn_ambient_environment        N~2~
_diffrn_ambient_temperature        100.01(10)
_diffrn_detector                   'CCD plate'
_diffrn_detector_area_resol_mean   10.3829
_diffrn_detector_type              Atlas
_diffrn_measured_fraction_theta_full  1.000
_diffrn_measured_fraction_theta_max  0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω   -120.00 -46.00   1.00    1.25    --  -41.44 178.00  90.00   74
  2  ω   -115.00 -13.00   1.00    1.25    --  -41.44 -57.00   0.00  102
  3  ω     62.00  98.00   1.00    1.25    --   41.44  19.00  90.00   36
  4  ω    115.00 174.00   1.00    5.00    --  112.00  77.00 150.00   59
  5  ω    100.00 144.00   1.00    5.00    --  112.00 -77.00  30.00   44
  6  ω     40.00  96.00   1.00    5.00    --  112.00-114.00  26.00   56
  7  ω     44.00  72.00   1.00    5.00    --  112.00 -77.00  30.00   28
  8  ω     67.00 134.00   1.00    5.00    --  112.00 -35.00 104.00   67
  9  ω     48.00 112.00   1.00    5.00    --  112.00-126.00 120.00   64
 10  ω    109.00 154.00   1.00    5.00    --  112.00 126.00  30.00   45
 11  ω     88.00 115.00   1.00    5.00    --  112.00  45.00-180.00   27
 12  ω    145.00 178.00   1.00    5.00    --  112.00  45.00-180.00   33
 13  ω    135.00 162.00   1.00    5.00    --  112.00 126.00 -30.00   27
;
_diffrn_measurement_device         'four-circle diffractometer'
_diffrn_measurement_device_type    'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method         'ω scans'
_diffrn_orient_matrix_type        
 'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11        -0.0524058000
_diffrn_orient_matrix_UB_12        -0.0412082000
_diffrn_orient_matrix_UB_13        -0.1502371000
_diffrn_orient_matrix_UB_21        -0.0030247000
_diffrn_orient_matrix_UB_22        -0.1264256000
_diffrn_orient_matrix_UB_23        0.0608247000
_diffrn_orient_matrix_UB_31        -0.1059116000
_diffrn_orient_matrix_UB_32        0.0237909000
_diffrn_orient_matrix_UB_33        0.0613369000
_diffrn_radiation_monochromator    mirror
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             'Cu K\a'
_diffrn_radiation_wavelength       1.54184
_diffrn_source                     'micro-focus sealed X-ray tube'
_diffrn_source_type                'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  2439
_reflns_number_total               2597
_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         'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection         'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction          'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_molecular_graphics      'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max           0.237
_refine_diff_density_min           -0.324
_refine_diff_density_rms           0.056
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.027
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       191
_refine_ls_number_reflns           2597
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0418
_refine_ls_R_factor_gt             0.0398
_refine_ls_restrained_S_all        1.027
_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)+(0.0629P)²+0.5914P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1050
_refine_ls_wR_factor_ref           0.1071
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C17(H17), C13(H13), C8(H8), C5(H5), C14(H14), C16(H16), C6(H6),
 C3(H3), C15(H15), C2(H2)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 1.07671(6) 0.53235(8) 0.28771(10) 0.0243(2) Uani 1 1 d . . . . .
 O2 O 0.40537(6) 0.44383(8) 0.41054(10) 0.0133(2) Uani 1 1 d . . . . .
 O1 O 0.49658(7) 0.10555(8) 0.24031(11) 0.0171(2) Uani 1 1 d . . . . .
 H1 H 0.529580 0.055997 0.192725 0.026 Uiso 1 1 calc R U . . .
 N1 N 0.60766(8) 0.37626(9) 0.35356(12) 0.0125(2) Uani 1 1 d . . . . .
 H1A H 0.607576 0.447487 0.391461 0.015 Uiso 1 1 calc R U . . .
 C10 C 0.52408(9) 0.30026(11) 0.34752(14) 0.0123(3) Uani 1 1 d . . . . .
 C11 C 0.42659(9) 0.33701(11) 0.39502(13) 0.0115(3) Uani 1 1 d . . . . .
 C9 C 0.55684(9) 0.19842(11) 0.27390(14) 0.0129(3) Uani 1 1 d . . . . .
 C17 C 0.37683(10) 0.14184(11) 0.49856(14) 0.0149(3) Uani 1 1 d . . . . .
 H17 H 0.447364 0.124664 0.520579 0.018 Uiso 1 1 calc R U . . .
 C7 C 0.68901(9) 0.32492(11) 0.29281(14) 0.0133(3) Uani 1 1 d . . . . .
 C4 C 0.79046(9) 0.38031(11) 0.29313(14) 0.0140(3) Uani 1 1 d . . . . .
 C12 C 0.34847(9) 0.24768(11) 0.42959(13) 0.0127(3) Uani 1 1 d . . . . .
 C13 C 0.24453(9) 0.27307(11) 0.39877(14) 0.0148(3) Uani 1 1 d . . . . .
 H13 H 0.224701 0.345362 0.352847 0.018 Uiso 1 1 calc R U . . .
 C8 C 0.65885(9) 0.21459(11) 0.23927(14) 0.0144(3) Uani 1 1 d . . . . .
 H8 H 0.700121 0.160482 0.188603 0.017 Uiso 1 1 calc R U . . .
 C5 C 0.80982(10) 0.48853(12) 0.36164(15) 0.0165(3) Uani 1 1 d . . . . .
 H5 H 0.756296 0.527662 0.409479 0.020 Uiso 1 1 calc R U . . .
 C1 C 0.98245(10) 0.48169(13) 0.29038(15) 0.0179(3) Uani 1 1 d . . . . .
 C14 C 0.17049(10) 0.19246(12) 0.43540(15) 0.0177(3) Uani 1 1 d . . . . .
 H14 H 0.099864 0.209447 0.413958 0.021 Uiso 1 1 calc R U . . .
 C16 C 0.30233(10) 0.06160(12) 0.53509(15) 0.0175(3) Uani 1 1 d . . . . .
 H16 H 0.321867 -0.010529 0.581710 0.021 Uiso 1 1 calc R U . . .
 C6 C 0.90625(10) 0.53985(12) 0.36090(15) 0.0178(3) Uani 1 1 d . . . . .
 H6 H 0.919365 0.613466 0.407990 0.021 Uiso 1 1 calc R U . . .
 C3 C 0.87010(10) 0.32381(12) 0.22291(16) 0.0193(3) Uani 1 1 d . . . . .
 H3 H 0.857840 0.250058 0.175732 0.023 Uiso 1 1 calc R U . . .
 C15 C 0.19920(10) 0.08677(12) 0.50347(15) 0.0189(3) Uani 1 1 d . . . . .
 H15 H 0.148193 0.031773 0.528331 0.023 Uiso 1 1 calc R U . . .
 C2 C 0.96695(10) 0.37455(12) 0.22154(17) 0.0209(3) Uani 1 1 d . . . . .
 H2 H 1.021147 0.336236 0.174250 0.025 Uiso 1 1 calc R U . . .


_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 C1 1.3601(15) . ?
 O2 C11 1.2592(15) . ?
 O1 H1 0.8400 . ?
 O1 C9 1.3428(15) . ?
 N1 H1A 0.8800 . ?
 N1 C10 1.3917(15) . ?
 N1 C7 1.3520(16) . ?
 C10 C11 1.4262(16) . ?
 C10 C9 1.4124(17) . ?
 C11 C12 1.4860(17) . ?
 C9 C8 1.3954(17) . ?
 C17 H17 0.9500 . ?
 C17 C12 1.3953(18) . ?
 C17 C16 1.3873(18) . ?
 C7 C4 1.4664(17) . ?
 C7 C8 1.3947(18) . ?
 C4 C5 1.3940(18) . ?
 C4 C3 1.4003(18) . ?
 C12 C13 1.3981(17) . ?
 C13 H13 0.9500 . ?
 C13 C14 1.3861(18) . ?
 C8 H8 0.9500 . ?
 C5 H5 0.9500 . ?
 C5 C6 1.3878(18) . ?
 C1 C6 1.3765(19) . ?
 C1 C2 1.377(2) . ?
 C14 H14 0.9500 . ?
 C14 C15 1.391(2) . ?
 C16 H16 0.9500 . ?
 C16 C15 1.388(2) . ?
 C6 H6 0.9500 . ?
 C3 H3 0.9500 . ?
 C3 C2 1.3903(19) . ?
 C15 H15 0.9500 . ?
 C2 H2 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
 C9 O1 H1 109.5 . . ?
 C10 N1 H1A 124.9 . . ?
 C7 N1 H1A 124.9 . . ?
 C7 N1 C10 110.22(10) . . ?
 N1 C10 C11 121.01(11) . . ?
 N1 C10 C9 105.87(10) . . ?
 C9 C10 C11 132.71(11) . . ?
 O2 C11 C10 121.51(11) . . ?
 O2 C11 C12 118.91(10) . . ?
 C10 C11 C12 119.58(11) . . ?
 O1 C9 C10 124.32(11) . . ?
 O1 C9 C8 127.48(11) . . ?
 C8 C9 C10 108.16(11) . . ?
 C12 C17 H17 119.9 . . ?
 C16 C17 H17 119.9 . . ?
 C16 C17 C12 120.19(12) . . ?
 N1 C7 C4 122.78(11) . . ?
 N1 C7 C8 108.40(11) . . ?
 C8 C7 C4 128.78(11) . . ?
 C5 C4 C7 121.56(11) . . ?
 C5 C4 C3 118.88(12) . . ?
 C3 C4 C7 119.56(12) . . ?
 C17 C12 C11 121.15(11) . . ?
 C17 C12 C13 119.70(11) . . ?
 C13 C12 C11 119.08(11) . . ?
 C12 C13 H13 120.1 . . ?
 C14 C13 C12 119.82(12) . . ?
 C14 C13 H13 120.1 . . ?
 C9 C8 H8 126.3 . . ?
 C7 C8 C9 107.31(11) . . ?
 C7 C8 H8 126.3 . . ?
 C4 C5 H5 119.6 . . ?
 C6 C5 C4 120.87(12) . . ?
 C6 C5 H5 119.6 . . ?
 F1 C1 C6 118.71(12) . . ?
 F1 C1 C2 118.63(12) . . ?
 C6 C1 C2 122.66(12) . . ?
 C13 C14 H14 119.9 . . ?
 C13 C14 C15 120.26(12) . . ?
 C15 C14 H14 119.9 . . ?
 C17 C16 H16 120.0 . . ?
 C17 C16 C15 119.96(12) . . ?
 C15 C16 H16 120.0 . . ?
 C5 C6 H6 120.7 . . ?
 C1 C6 C5 118.50(12) . . ?
 C1 C6 H6 120.7 . . ?
 C4 C3 H3 119.7 . . ?
 C2 C3 C4 120.66(13) . . ?
 C2 C3 H3 119.7 . . ?
 C14 C15 H15 120.0 . . ?
 C16 C15 C14 120.07(12) . . ?
 C16 C15 H15 120.0 . . ?
 C1 C2 C3 118.42(12) . . ?
 C1 C2 H2 120.8 . . ?
 C3 C2 H2 120.8 . . ?

loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 F1 C1 C6 C5 179.18(11) . . . . ?
 F1 C1 C2 C3 -179.20(12) . . . . ?
 O2 C11 C12 C17 -142.43(12) . . . . ?
 O2 C11 C12 C13 34.46(16) . . . . ?
 O1 C9 C8 C7 178.47(12) . . . . ?
 N1 C10 C11 O2 16.69(18) . . . . ?
 N1 C10 C11 C12 -162.31(11) . . . . ?
 N1 C10 C9 O1 -177.11(11) . . . . ?
 N1 C10 C9 C8 0.74(14) . . . . ?
 N1 C7 C4 C5 2.3(2) . . . . ?
 N1 C7 C4 C3 -177.54(12) . . . . ?
 N1 C7 C8 C9 -1.95(14) . . . . ?
 C10 N1 C7 C4 -175.40(11) . . . . ?
 C10 N1 C7 C8 2.48(14) . . . . ?
 C10 C11 C12 C17 36.59(16) . . . . ?
 C10 C11 C12 C13 -146.52(12) . . . . ?
 C10 C9 C8 C7 0.71(14) . . . . ?
 C11 C10 C9 O1 -4.6(2) . . . . ?
 C11 C10 C9 C8 173.20(13) . . . . ?
 C11 C12 C13 C14 -177.64(11) . . . . ?
 C9 C10 C11 O2 -154.84(13) . . . . ?
 C9 C10 C11 C12 26.2(2) . . . . ?
 C17 C12 C13 C14 -0.70(18) . . . . ?
 C17 C16 C15 C14 -0.1(2) . . . . ?
 C7 N1 C10 C11 -175.53(11) . . . . ?
 C7 N1 C10 C9 -1.99(14) . . . . ?
 C7 C4 C5 C6 -179.95(12) . . . . ?
 C7 C4 C3 C2 179.94(12) . . . . ?
 C4 C7 C8 C9 175.76(12) . . . . ?
 C4 C5 C6 C1 0.2(2) . . . . ?
 C4 C3 C2 C1 -0.2(2) . . . . ?
 C12 C17 C16 C15 -0.23(19) . . . . ?
 C12 C13 C14 C15 0.37(19) . . . . ?
 C13 C14 C15 C16 0.0(2) . . . . ?
 C8 C7 C4 C5 -175.09(12) . . . . ?
 C8 C7 C4 C3 5.0(2) . . . . ?
 C5 C4 C3 C2 0.1(2) . . . . ?
 C16 C17 C12 C11 177.50(11) . . . . ?
 C16 C17 C12 C13 0.64(18) . . . . ?
 C6 C1 C2 C3 0.4(2) . . . . ?
 C3 C4 C5 C6 -0.1(2) . . . . ?
 C2 C1 C6 C5 -0.4(2) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max  3.662
_oxdiff_exptl_absorpt_empirical_full_min  0.570
