#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/45/2214594.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2214594
loop_
_publ_author_name
'Butcher, Ray J.'
'Jasinski, Jerry P.'
'Narayana, B.'
'Lakshmana, K.'
'Yathirajan, H. S.'
_publ_section_title
;
 (2E)-3-(4-Fluorophenyl)-1-(3-hydroxyphenyl)prop-2-en-1-one
;
_journal_coeditor_code           CI2418
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3586
_journal_page_last               o3586
_journal_paper_doi               10.1107/S1600536807034964
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C15 H11 F O2'
_chemical_formula_moiety         'C15 H11 F O2'
_chemical_formula_sum            'C15 H11 F O2'
_chemical_formula_weight         242.24
_chemical_name_systematic
;
(2E)-3-(4-Fluorophenyl)-1-(3-hydroxyphenyl)prop-2-en-1-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 104.311(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4149(4)
_cell_length_b                   11.3162(6)
_cell_length_c                   14.7472(8)
_cell_measurement_reflns_used    5107
_cell_measurement_temperature    203
_cell_measurement_theta_max      32.5187
_cell_measurement_theta_min      4.8403
_cell_volume                     1199.02(12)
_computing_cell_refinement       CrysAlisPro
_computing_data_collection       'CrysAlisPro (Oxford Diffraction, 2007)'
_computing_data_reduction        CrysAlisPro
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      203
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_sigmaI/netI    0.0654
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16754
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.46
_diffrn_reflns_theta_min         4.84
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64338
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.166
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         4038
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.1053
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0687P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1449
_reflns_number_gt                1916
_reflns_number_total             4038
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2418.cif
_cod_data_source_block           I
_cod_original_cell_volume        1199.01(11)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2214594
_cod_database_fobs_code          2214594
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
_atom_site_occupancy
F F 0.53494(15) 0.34667(10) -0.46126(6) 0.0827(4) Uani d . 1
O O1 0.71674(13) 0.81902(9) 0.33109(6) 0.0491(3) Uani d . 1
H H1 0.6731 0.8786 0.3507 0.059 Uiso d . 1
O O2 0.83919(12) 0.53556(8) 0.10376(6) 0.0449(3) Uani d . 1
C C1 0.65119(16) 0.70409(10) 0.09520(8) 0.0318(3) Uani d . 1
C C2 0.71346(16) 0.71937(11) 0.19185(8) 0.0339(3) Uani d . 1
H H2A 0.7999 0.6658 0.2270 0.041 Uiso calc R 1
C C3 0.65035(17) 0.81164(12) 0.23650(8) 0.0360(3) Uani d . 1
C C4 0.52401(19) 0.89189(12) 0.18486(9) 0.0436(3) Uani d . 1
H H4A 0.4812 0.9555 0.2148 0.052 Uiso calc R 1
C C5 0.4616(2) 0.87745(13) 0.08907(10) 0.0488(4) Uani d . 1
H H5A 0.3759 0.9317 0.0543 0.059 Uiso calc R 1
C C6 0.52293(19) 0.78494(12) 0.04362(9) 0.0426(3) Uani d . 1
H H6A 0.4790 0.7762 -0.0215 0.051 Uiso calc R 1
C C7 0.72278(15) 0.60043(10) 0.05300(8) 0.0321(3) Uani d . 1
C C8 0.65602(16) 0.57558(11) -0.04758(8) 0.0327(3) Uani d . 1
H H8A 0.5600 0.6220 -0.0841 0.039 Uiso calc R 1
C C9 0.72904(16) 0.48853(11) -0.08792(9) 0.0347(3) Uani d . 1
H H9A 0.8244 0.4445 -0.0485 0.042 Uiso calc R 1
C C10 0.67813(16) 0.45384(11) -0.18606(9) 0.0344(3) Uani d . 1
C C11 0.54868(19) 0.51720(12) -0.25370(9) 0.0427(3) Uani d . 1
H H11A 0.4933 0.5852 -0.2358 0.051 Uiso calc R 1
C C12 0.5007(2) 0.48226(14) -0.34577(10) 0.0523(4) Uani d . 1
H H12A 0.4133 0.5252 -0.3908 0.063 Uiso calc R 1
C C13 0.5838(2) 0.38287(15) -0.37027(10) 0.0522(4) Uani d . 1
C C14 0.7107(2) 0.31840(14) -0.30732(11) 0.0514(4) Uani d . 1
H H14A 0.7654 0.2508 -0.3263 0.062 Uiso calc R 1
C C15 0.75793(18) 0.35409(12) -0.21479(10) 0.0418(3) Uani d . 1
H H15A 0.8454 0.3101 -0.1706 0.050 Uiso calc R 1
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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 O1 H1 109.5
C2 C1 C6 118.83(11)
C2 C1 C7 117.59(11)
C6 C1 C7 123.58(11)
C3 C2 C1 121.10(11)
C3 C2 H2A 119.4
C1 C2 H2A 119.4
O1 C3 C2 117.18(11)
O1 C3 C4 123.05(12)
C2 C3 C4 119.77(12)
C5 C4 C3 119.51(13)
C5 C4 H4A 120.2
C3 C4 H4A 120.2
C6 C5 C4 121.25(13)
C6 C5 H5A 119.4
C4 C5 H5A 119.4
C5 C6 C1 119.53(12)
C5 C6 H6A 120.2
C1 C6 H6A 120.2
O2 C7 C8 120.57(11)
O2 C7 C1 118.94(11)
C8 C7 C1 120.49(10)
C9 C8 C7 121.27(11)
C9 C8 H8A 119.4
C7 C8 H8A 119.4
C8 C9 C10 127.49(12)
C8 C9 H9A 116.3
C10 C9 H9A 116.3
C15 C10 C11 117.91(12)
C15 C10 C9 119.80(12)
C11 C10 C9 122.28(12)
C12 C11 C10 121.45(13)
C12 C11 H11A 119.3
C10 C11 H11A 119.3
C13 C12 C11 118.18(14)
C13 C12 H12A 120.9
C11 C12 H12A 120.9
C14 C13 F 118.79(14)
C14 C13 C12 122.68(13)
F C13 C12 118.53(14)
C13 C14 C15 118.74(14)
C13 C14 H14A 120.6
C15 C14 H14A 120.6
C14 C15 C10 121.04(13)
C14 C15 H15A 119.5
C10 C15 H15A 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F C13 1.3635(16)
O1 C3 1.3622(15)
O1 H1 0.83
O2 C7 1.2348(14)
C1 C2 1.3962(16)
C1 C6 1.4009(17)
C1 C7 1.4861(17)
C2 C3 1.3766(18)
C2 H2A 0.94
C3 C4 1.3890(18)
C4 C5 1.3832(18)
C4 H4A 0.94
C5 C6 1.379(2)
C5 H5A 0.94
C6 H6A 0.94
C7 C8 1.4700(17)
C8 C9 1.3330(17)
C8 H8A 0.94
C9 C10 1.4564(17)
C9 H9A 0.94
C10 C15 1.3884(18)
C10 C11 1.3989(18)
C11 C12 1.3739(19)
C11 H11A 0.94
C12 C13 1.373(2)
C12 H12A 0.94
C13 C14 1.359(2)
C14 C15 1.3825(19)
C14 H14A 0.94
C15 H15A 0.94
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
O1 H1 O2 2_655 0.83 1.91 2.7013(13) 159
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
C6 C1 C2 C3 0.27(18)
C7 C1 C2 C3 -178.49(11)
C1 C2 C3 O1 179.23(10)
C1 C2 C3 C4 -0.65(19)
O1 C3 C4 C5 -179.26(12)
C2 C3 C4 C5 0.6(2)
C3 C4 C5 C6 -0.2(2)
C4 C5 C6 C1 -0.2(2)
C2 C1 C6 C5 0.15(19)
C7 C1 C6 C5 178.82(13)
C2 C1 C7 O2 -3.07(16)
C6 C1 C7 O2 178.24(11)
C2 C1 C7 C8 176.94(10)
C6 C1 C7 C8 -1.75(18)
O2 C7 C8 C9 -5.25(18)
C1 C7 C8 C9 174.75(11)
C7 C8 C9 C10 -179.81(10)
C8 C9 C10 C15 -174.46(12)
C8 C9 C10 C11 4.9(2)
C15 C10 C11 C12 0.2(2)
C9 C10 C11 C12 -179.18(12)
C10 C11 C12 C13 -0.2(2)
C11 C12 C13 C14 0.0(2)
C11 C12 C13 F 179.08(13)
F C13 C14 C15 -178.96(12)
C12 C13 C14 C15 0.1(2)
C13 C14 C15 C10 -0.1(2)
C11 C10 C15 C14 -0.10(19)
C9 C10 C15 C14 179.32(12)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655289
2 PubChem 6258426
