#------------------------------------------------------------------------------
#$Date: 2018-12-18 05:19:41 +0200 (Tue, 18 Dec 2018) $
#$Revision: 212634 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/27/2242785.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_2242785
loop_
_publ_author_name
'Wong, Qin Ai'
'Chia, Tze Shyang'
'Kwong, Huey Chong'
'Chidan Kumar, C. S.'
'Quah, Ching Kheng'
'Arafath, Md. Azharul'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of a chalcone
 derivative:
 (E)-3-(4-fluorophenyl)-1-(4-nitrophenyl)prop-2-en-1-one
;
_journal_coeditor_code           IS5506
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              53
_journal_page_last               57
_journal_paper_doi               10.1107/S2056989018017450
_journal_volume                  75
_journal_year                    2019
_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-(4-nitrophenyl)prop-2-en-1-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 91.963(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.8860(5)
_cell_length_b                   13.2324(16)
_cell_length_c                   24.199(3)
_cell_measurement_reflns_used    4607
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.40
_cell_measurement_theta_min      2.28
_cell_volume                     1243.6(3)
_computing_cell_refinement
;
SAINT (Bruker, 2009)
;
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_data_reduction
;
SAINT (Bruker, 2009)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material
;
PLATON (Spek, 2009) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS2013 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART APEXII DUO CCD area-detector'
_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  0.0255
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            10823
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         1.754
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.9261
_exptl_absorpt_correction_T_min  0.7937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2009)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.488
_exptl_crystal_size_mid          0.353
_exptl_crystal_size_min          0.310
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.171
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2418
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0425
_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)+(0.0720P)²+0.3042P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1375
_reflns_number_gt                1922
_reflns_number_total             2418
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            is5506sup1.cif
_cod_data_source_block           I
_cod_database_code               2242785
_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.
;
_shelx_estimated_absorpt_t_min   0.947
_shelx_estimated_absorpt_t_max   0.966
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'
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_occupancy
F F1 0.7362(4) -0.01394(9) 0.57883(5) 0.0899(5) Uani d 1
O O1 -0.1032(4) 0.85915(12) 0.77829(6) 0.0784(5) Uani d 1
O O2 0.0898(6) 0.97163(12) 0.72386(8) 0.1026(7) Uani d 1
O O3 0.7296(4) 0.61266(9) 0.55381(5) 0.0665(4) Uani d 1
N N1 0.0476(4) 0.88363(12) 0.73723(6) 0.0578(4) Uani d 1
C C1 0.3037(4) 0.63109(12) 0.68456(6) 0.0460(4) Uani d 1
H H1A 0.2995 0.5638 0.6955 0.055 Uiso calc 1
C C2 0.1758(4) 0.70499(13) 0.71878(6) 0.0479(4) Uani d 1
H H2A 0.0857 0.6880 0.7527 0.057 Uiso calc 1
C C3 0.1848(4) 0.80391(12) 0.70162(6) 0.0443(4) Uani d 1
C C4 0.3144(5) 0.83206(12) 0.65149(7) 0.0502(4) Uani d 1
H H4A 0.3157 0.8995 0.6407 0.060 Uiso calc 1
C C5 0.4418(4) 0.75795(12) 0.61790(6) 0.0474(4) Uani d 1
H H5A 0.5311 0.7757 0.5841 0.057 Uiso calc 1
C C6 0.4388(4) 0.65682(11) 0.63385(6) 0.0397(4) Uani d 1
C C7 0.5886(4) 0.58109(12) 0.59466(6) 0.0437(4) Uani d 1
C C8 0.5671(4) 0.47246(12) 0.60636(7) 0.0465(4) Uani d 1
H H8A 0.4609 0.4501 0.6380 0.056 Uiso calc 1
C C9 0.6995(4) 0.40594(13) 0.57171(6) 0.0461(4) Uani d 1
H H9A 0.8020 0.4332 0.5409 0.055 Uiso calc 1
C C10 0.7052(4) 0.29630(12) 0.57557(6) 0.0441(4) Uani d 1
C C11 0.8374(4) 0.24150(13) 0.53176(7) 0.0498(4) Uani d 1
H H11A 0.9211 0.2760 0.5015 0.060 Uiso calc 1
C C12 0.8463(5) 0.13763(14) 0.53240(8) 0.0573(5) Uani d 1
H H12A 0.9314 0.1015 0.5029 0.069 Uiso calc 1
C C13 0.7264(5) 0.08894(13) 0.57778(7) 0.0571(5) Uani d 1
C C14 0.5966(5) 0.13871(13) 0.62234(7) 0.0571(5) Uani d 1
H H14A 0.5188 0.1032 0.6526 0.069 Uiso calc 1
C C15 0.5851(4) 0.24251(13) 0.62076(7) 0.0504(4) Uani d 1
H H15A 0.4958 0.2776 0.6503 0.061 Uiso calc 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
O1 N1 O2 122.95(16)
O1 N1 C3 118.80(16)
O2 N1 C3 118.24(15)
C2 C1 C6 120.53(14)
C2 C1 H1A 119.7
C6 C1 H1A 119.7
C3 C2 C1 118.60(14)
C3 C2 H2A 120.7
C1 C2 H2A 120.7
C2 C3 C4 122.43(15)
C2 C3 N1 119.47(14)
C4 C3 N1 118.09(15)
C5 C4 C3 118.43(15)
C5 C4 H4A 120.8
C3 C4 H4A 120.8
C4 C5 C6 120.95(14)
C4 C5 H5A 119.5
C6 C5 H5A 119.5
C5 C6 C1 119.06(14)
C5 C6 C7 117.17(13)
C1 C6 C7 123.78(14)
O3 C7 C8 121.43(15)
O3 C7 C6 118.36(14)
C8 C7 C6 120.20(13)
C9 C8 C7 120.02(14)
C9 C8 H8A 120.0
C7 C8 H8A 120.0
C8 C9 C10 128.67(15)
C8 C9 H9A 115.7
C10 C9 H9A 115.7
C11 C10 C15 118.08(15)
C11 C10 C9 118.33(14)
C15 C10 C9 123.59(14)
C12 C11 C10 121.34(15)
C12 C11 H11A 119.3
C10 C11 H11A 119.3
C13 C12 C11 118.06(16)
C13 C12 H12A 121.0
C11 C12 H12A 121.0
F1 C13 C12 118.38(16)
F1 C13 C14 118.37(16)
C12 C13 C14 123.25(17)
C13 C14 C15 118.00(15)
C13 C14 H14A 121.0
C15 C14 H14A 121.0
C14 C15 C10 121.26(15)
C14 C15 H15A 119.4
C10 C15 H15A 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C13 1.362(2)
O1 N1 1.2147(19)
O2 N1 1.221(2)
O3 C7 1.2204(19)
N1 C3 1.473(2)
C1 C2 1.385(2)
C1 C6 1.393(2)
C1 H1A 0.9300
C2 C3 1.374(2)
C2 H2A 0.9300
C3 C4 1.381(2)
C4 C5 1.377(2)
C4 H4A 0.9300
C5 C6 1.393(2)
C5 H5A 0.9300
C6 C7 1.510(2)
C7 C8 1.468(2)
C8 C9 1.331(2)
C8 H8A 0.9300
C9 C10 1.454(2)
C9 H9A 0.9300
C10 C11 1.397(2)
C10 C15 1.398(2)
C11 C12 1.375(2)
C11 H11A 0.9300
C12 C13 1.369(3)
C12 H12A 0.9300
C13 C14 1.374(2)
C14 C15 1.375(2)
C14 H14A 0.9300
C15 H15A 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 F1 1_565 0.93 2.53 3.183(2) 128 yes
C11 H11A O3 3_766 0.93 2.43 3.329(2) 161 yes
C15 H15A O1 2_546 0.93 2.58 3.489(2) 166 yes
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 0.0(3)
C1 C2 C3 C4 0.4(3)
C1 C2 C3 N1 179.54(15)
O1 N1 C3 C2 -7.6(2)
O2 N1 C3 C2 172.67(18)
O1 N1 C3 C4 171.54(17)
O2 N1 C3 C4 -8.2(3)
C2 C3 C4 C5 -0.6(3)
N1 C3 C4 C5 -179.74(15)
C3 C4 C5 C6 0.3(3)
C4 C5 C6 C1 0.1(3)
C4 C5 C6 C7 -179.16(15)
C2 C1 C6 C5 -0.3(2)
C2 C1 C6 C7 178.91(15)
C5 C6 C7 O3 6.1(2)
C1 C6 C7 O3 -173.10(16)
C5 C6 C7 C8 -174.65(15)
C1 C6 C7 C8 6.1(2)
O3 C7 C8 C9 -0.8(3)
C6 C7 C8 C9 -179.99(15)
C7 C8 C9 C10 -179.96(15)
C8 C9 C10 C11 175.31(17)
C8 C9 C10 C15 -4.6(3)
C15 C10 C11 C12 0.8(3)
C9 C10 C11 C12 -179.15(16)
C10 C11 C12 C13 -1.0(3)
C11 C12 C13 F1 -179.66(17)
C11 C12 C13 C14 0.4(3)
F1 C13 C14 C15 -179.50(17)
C12 C13 C14 C15 0.5(3)
C13 C14 C15 C10 -0.7(3)
C11 C10 C15 C14 0.1(3)
C9 C10 C15 C14 -179.98(16)

_cod_database_fobs_code 2242785
