#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/62/2226218.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_2226218
loop_
_publ_author_name
'Pan, Zhi-fang'
_publ_section_title
;
 (E)-3-(4-Fluorophenyl)-1-(2-nitrophenyl)prop-2-en-1-one
;
_journal_coeditor_code           LH5041
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1414
_journal_paper_doi               10.1107/S160053681001809X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H10 F N O3'
_chemical_formula_moiety         'C15 H10 F N O3'
_chemical_formula_sum            'C15 H10 F N O3'
_chemical_formula_weight         271.24
_chemical_name_systematic
;
(E)-3-(4-Fluorophenyl)-1-(2-nitrophenyl)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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.72(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7698(16)
_cell_length_b                   17.072(3)
_cell_length_c                   9.759(2)
_cell_measurement_reflns_used    2218
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.18
_cell_volume                     1285.6(4)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0163
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12293
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.18
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       bar
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.192
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2921
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0695P)²+0.2079P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1406
_reflns_number_gt                2218
_reflns_number_total             2921
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5041.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        1285.6(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2226218
_cod_database_fobs_code          2226218
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O3 0.08601(15) 0.10025(8) 0.43283(13) 0.0659(4) Uani d . 1 . .
C C7 0.22626(19) 0.11601(9) 0.49650(15) 0.0449(3) Uani d . 1 . .
C C9 0.18075(19) 0.04525(9) 0.70546(15) 0.0469(3) Uani d . 1 . .
H H9A 0.0871 0.0226 0.6517 0.056 Uiso calc R 1 . .
C C6 0.36095(18) 0.15551(8) 0.42269(14) 0.0418(3) Uani d . 1 . .
C C8 0.27359(19) 0.09685(9) 0.64309(15) 0.0472(4) Uani d . 1 . .
H H8A 0.3689 0.1209 0.6924 0.057 Uiso calc R 1 . .
C C15 0.1386(2) -0.05036(9) 0.88492(16) 0.0495(4) Uani d . 1 . .
H H15A 0.0725 -0.0794 0.8173 0.059 Uiso calc R 1 . .
F F1 0.27941(18) -0.06060(9) 1.24775(11) 0.0933(4) Uani d . 1 . .
N N1 0.13799(19) 0.23833(8) 0.29207(17) 0.0589(4) Uani d . 1 . .
C C10 0.21056(19) 0.02052(9) 0.84967(15) 0.0449(3) Uani d . 1 . .
C C11 0.3057(2) 0.06445(10) 0.95326(16) 0.0522(4) Uani d . 1 . .
H H11A 0.3536 0.1122 0.9317 0.063 Uiso calc R 1 . .
C C1 0.31757(19) 0.20928(9) 0.31805(16) 0.0471(4) Uani d . 1 . .
C C5 0.5339(2) 0.13342(10) 0.44662(16) 0.0521(4) Uani d . 1 . .
H H5A 0.5685 0.0977 0.5165 0.063 Uiso calc R 1 . .
C C14 0.1637(2) -0.07817(11) 1.01808(18) 0.0569(4) Uani d . 1 . .
H H14A 0.1179 -0.1261 1.0408 0.068 Uiso calc R 1 . .
C C12 0.3287(2) 0.03713(12) 1.08766(17) 0.0595(5) Uani d . 1 . .
H H12A 0.3911 0.0661 1.1574 0.071 Uiso calc R 1 . .
C C13 0.2572(2) -0.03371(12) 1.11546(16) 0.0593(5) Uani d . 1 . .
C C4 0.6559(2) 0.16380(12) 0.36778(19) 0.0634(5) Uani d . 1 . .
H H4A 0.7714 0.1487 0.3857 0.076 Uiso calc R 1 . .
O O2 0.07277(18) 0.26603(9) 0.38907(18) 0.0830(5) Uani d . 1 . .
C C2 0.4367(2) 0.23925(11) 0.2374(2) 0.0643(5) Uani d . 1 . .
H H2A 0.4026 0.2745 0.1667 0.077 Uiso calc R 1 . .
C C3 0.6067(3) 0.21593(13) 0.2637(2) 0.0702(5) Uani d . 1 . .
H H3A 0.6888 0.2356 0.2106 0.084 Uiso calc R 1 . .
O O1 0.0655(2) 0.23414(11) 0.17437(17) 0.0930(5) Uani d . 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'
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O3 C7 C8 . . 123.58(14) ?
O3 C7 C6 . . 119.14(13) ?
C8 C7 C6 . . 117.27(12) ?
C8 C9 C10 . . 126.77(14) ?
C8 C9 H9A . . 116.6 ?
C10 C9 H9A . . 116.6 ?
C1 C6 C5 . . 116.81(14) ?
C1 C6 C7 . . 121.96(13) ?
C5 C6 C7 . . 120.89(14) ?
C9 C8 C7 . . 120.32(14) ?
C9 C8 H8A . . 119.8 ?
C7 C8 H8A . . 119.8 ?
C14 C15 C10 . . 121.09(16) ?
C14 C15 H15A . . 119.5 ?
C10 C15 H15A . . 119.5 ?
O2 N1 O1 . . 124.40(16) ?
O2 N1 C1 . . 117.87(15) ?
O1 N1 C1 . . 117.71(16) ?
C15 C10 C11 . . 118.74(14) ?
C15 C10 C9 . . 117.76(14) ?
C11 C10 C9 . . 123.49(15) ?
C12 C11 C10 . . 120.21(16) ?
C12 C11 H11A . . 119.9 ?
C10 C11 H11A . . 119.9 ?
C2 C1 C6 . . 122.96(15) ?
C2 C1 N1 . . 117.45(15) ?
C6 C1 N1 . . 119.56(13) ?
C6 C5 C4 . . 121.00(16) ?
C6 C5 H5A . . 119.5 ?
C4 C5 H5A . . 119.5 ?
C13 C14 C15 . . 118.23(17) ?
C13 C14 H14A . . 120.9 ?
C15 C14 H14A . . 120.9 ?
C13 C12 C11 . . 118.32(16) ?
C13 C12 H12A . . 120.8 ?
C11 C12 H12A . . 120.8 ?
C14 C13 F1 . . 118.22(18) ?
C14 C13 C12 . . 123.39(15) ?
F1 C13 C12 . . 118.40(17) ?
C3 C4 C5 . . 120.24(16) ?
C3 C4 H4A . . 119.9 ?
C5 C4 H4A . . 119.9 ?
C3 C2 C1 . . 118.66(17) ?
C3 C2 H2A . . 120.7 ?
C1 C2 H2A . . 120.7 ?
C4 C3 C2 . . 120.31(16) ?
C4 C3 H3A . . 119.8 ?
C2 C3 H3A . . 119.8 ?
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
O3 C7 . 1.2195(18) ?
C7 C8 . 1.472(2) ?
C7 C6 . 1.498(2) ?
C9 C8 . 1.330(2) ?
C9 C10 . 1.462(2) ?
C9 H9A . 0.9300 ?
C6 C1 . 1.385(2) ?
C6 C5 . 1.389(2) ?
C8 H8A . 0.9300 ?
C15 C14 . 1.376(2) ?
C15 C10 . 1.393(2) ?
C15 H15A . 0.9300 ?
F1 C13 . 1.3619(18) ?
N1 O2 . 1.220(2) ?
N1 O1 . 1.221(2) ?
N1 C1 . 1.475(2) ?
C10 C11 . 1.399(2) ?
C11 C12 . 1.384(2) ?
C11 H11A . 0.9300 ?
C1 C2 . 1.382(2) ?
C5 C4 . 1.390(2) ?
C5 H5A . 0.9300 ?
C14 C13 . 1.359(3) ?
C14 H14A . 0.9300 ?
C12 C13 . 1.371(3) ?
C12 H12A . 0.9300 ?
C4 C3 . 1.371(3) ?
C4 H4A . 0.9300 ?
C2 C3 . 1.375(3) ?
C2 H2A . 0.9300 ?
C3 H3A . 0.9300 ?
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
C4 H4A O3 1_655 0.93 2.57 3.500(2) 177.3 y
C5 H5A F1 3_657 0.93 2.54 3.396(2) 153.0 y
C9 H9A O3 . 0.93 2.51 2.836(2) 100.6 n
C9 H9A O3 3_556 0.93 2.57 3.411(2) 149.9 y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7730240
2 PubChem 9447932
