#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/31/2213109.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_2213109
loop_
_publ_author_name
'Farias, Adriano de P.'
'Visentin, Lorenzo do C.'
'Bordinhao, Jairo'
'Sobrinho, Dari C.'
'Ferreira, Jose C. N.'
_publ_section_title
;
 3-(3,5-Difluorophenyl)-1-phenylprop-2-en-1-one
;
_journal_coeditor_code           AV3072
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2770
_journal_page_last               o2771
_journal_paper_doi               10.1107/S1600536807012950
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C15 H10 F2 O'
_chemical_formula_moiety         'C15 H10 F2 O'
_chemical_formula_sum            'C15 H10 F2 O'
_chemical_formula_weight         244.24
_chemical_melting_point          382
_chemical_name_systematic
;
3-(3,5-Difluorophenyl)-1-phenylprop-2-en-1-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                92.80(3)
_cell_angle_beta                 96.10(3)
_cell_angle_gamma                99.82(3)
_cell_formula_units_Z            2
_cell_length_a                   6.0359(12)
_cell_length_b                   7.5002(15)
_cell_length_c                   13.637(3)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     603.4(2)
_computing_cell_refinement       'NDIRAX [Please provide reference]'
_computing_data_collection       'Nonius SUPERGUI [Please provide reference]'
_computing_data_reduction        NDIRAX
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ scans, and ω scans with κ offset'
_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  0.0791
_diffrn_reflns_av_sigmaI/netI    0.0983
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5771
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         5.14
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.112
_refine_diff_density_min         -0.146
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2222
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.938
_refine_ls_R_factor_all          0.1757
_refine_ls_R_factor_gt           0.0561
_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)+(0.0495P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1217
_reflns_number_gt                910
_reflns_number_total             2222
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            av3072.cif
_cod_data_source_block           I
_cod_original_cell_volume        603.5(2)
_cod_database_code               2213109
_cod_database_fobs_code          2213109
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C C1 0.8182(4) 0.3177(3) 0.65539(19) 0.0572(7) Uani d . 1
C C2 0.6251(4) 0.2694(3) 0.57814(18) 0.0568(7) Uani d . 1
H H2 0.4892 0.2080 0.5955 0.068 Uiso calc R 1
C C3 0.6350(4) 0.3090(3) 0.48527(19) 0.0550(7) Uani d . 1
H H3 0.7725 0.3731 0.4711 0.066 Uiso calc R 1
C C11 0.4568(4) 0.2648(3) 0.40177(18) 0.0504(7) Uani d . 1
C C12 0.5074(5) 0.3125(4) 0.3071(2) 0.0595(7) Uani d . 1
C C13 0.3427(5) 0.2671(4) 0.22886(19) 0.0690(8) Uani d . 1
C C14 0.1287(5) 0.1773(4) 0.2376(2) 0.0725(8) Uani d . 1
H H14 0.0196 0.1467 0.1832 0.087 Uiso calc R 1
C C15 0.0844(5) 0.1350(4) 0.3311(2) 0.0669(8) Uani d . 1
C C16 0.2397(4) 0.1765(3) 0.41326(19) 0.0581(7) Uani d . 1
H H16 0.2011 0.1464 0.4754 0.070 Uiso calc R 1
C C21 0.7903(4) 0.2839(3) 0.76174(18) 0.0507(6) Uani d . 1
C C22 0.5845(5) 0.2177(4) 0.7937(2) 0.0702(8) Uani d . 1
H H22 0.4550 0.1920 0.7483 0.084 Uiso calc R 1
C C23 0.5680(5) 0.1890(5) 0.8924(2) 0.0914(10) Uani d . 1
H H23 0.4281 0.1451 0.9130 0.110 Uiso calc R 1
C C24 0.7562(6) 0.2250(5) 0.9591(2) 0.0945(11) Uani d . 1
H H24 0.7446 0.2057 1.0254 0.113 Uiso calc R 1
C C25 0.9635(6) 0.2896(5) 0.9293(2) 0.0915(10) Uani d . 1
H H25 1.0924 0.3129 0.9751 0.110 Uiso calc R 1
C C26 0.9796(4) 0.3201(4) 0.8306(2) 0.0707(8) Uani d . 1
H H26 1.1197 0.3655 0.8107 0.085 Uiso calc R 1
F F1 0.3947(3) 0.3115(3) 0.13626(12) 0.1083(7) Uani d . 1
F F2 -0.1259(3) 0.0443(2) 0.34343(13) 0.0987(6) Uani d . 1
O O1 1.0039(3) 0.3846(3) 0.63268(13) 0.0946(7) Uani d . 1
H H12 0.660(4) 0.372(3) 0.2958(17) 0.073(8) Uiso 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 0.0030 0.0020 '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 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 '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_3
_geom_angle
O1 C1 C2 . 119.5(2)
O1 C1 C21 . 119.9(2)
C2 C1 C21 . 120.6(2)
C3 C2 C1 . 123.3(2)
C3 C2 H2 . 118.4
C1 C2 H2 . 118.4
C2 C3 C11 . 128.2(2)
C2 C3 H3 . 115.9
C11 C3 H3 . 115.9
C16 C11 C12 . 119.1(2)
C16 C11 C3 . 122.0(2)
C12 C11 C3 . 118.9(2)
C13 C12 C11 . 118.8(3)
C13 C12 O1 2_766 138.4(2)
C11 C12 O1 2_766 100.35(18)
C13 C12 H12 . 119.7(14)
C11 C12 H12 . 121.4(14)
C12 C13 C14 . 123.3(3)
C12 C13 F1 . 118.5(3)
C14 C13 F1 . 118.2(3)
C15 C14 C13 . 116.3(3)
C15 C14 H14 . 121.9
C13 C14 H14 . 121.9
F2 C15 C16 . 117.7(3)
F2 C15 C14 . 118.4(3)
C16 C15 C14 . 123.9(3)
C15 C16 C11 . 118.5(3)
C15 C16 H16 . 120.7
C11 C16 H16 . 120.7
C26 C21 C22 . 118.3(3)
C26 C21 C1 . 118.5(2)
C22 C21 C1 . 123.2(2)
C21 C22 C23 . 120.9(3)
C21 C22 H22 . 119.5
C23 C22 H22 . 119.5
C24 C23 C22 . 120.0(3)
C24 C23 H23 . 120.0
C22 C23 H23 . 120.0
C23 C24 C25 . 120.4(3)
C23 C24 H24 . 119.8
C25 C24 H24 . 119.8
C24 C25 C26 . 119.7(3)
C24 C25 H25 . 120.2
C26 C25 H25 . 120.2
C21 C26 C25 . 120.8(3)
C21 C26 H26 . 119.6
C25 C26 H26 . 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 O1 . 1.225(3)
C1 C2 . 1.469(3)
C1 C21 . 1.506(3)
C2 C3 . 1.320(3)
C2 H2 . 0.9300
C3 C11 . 1.464(3)
C3 H3 . 0.9300
C11 C16 . 1.392(3)
C11 C12 . 1.407(3)
C12 C13 . 1.366(4)
C12 O1 2_766 3.400(4)
C12 H12 . 0.98(2)
C13 C14 . 1.372(4)
C13 F1 . 1.376(3)
C14 C15 . 1.372(4)
C14 H14 . 0.9300
C15 F2 . 1.365(3)
C15 C16 . 1.369(3)
C16 H16 . 0.9300
C21 C26 . 1.380(3)
C21 C22 . 1.381(3)
C22 C23 . 1.384(4)
C22 H22 . 0.9300
C23 C24 . 1.357(4)
C23 H23 . 0.9300
C24 C25 . 1.374(4)
C24 H24 . 0.9300
C25 C26 . 1.387(4)
C25 H25 . 0.9300
C26 H26 . 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
C12 H12 O1 2_766 0.98(2) 2.56(2) 3.400(4) 143(2) 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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
O1 C1 C2 C3 . . -6.2(4)
C21 C1 C2 C3 . . 174.4(3)
C1 C2 C3 C11 . . 178.5(2)
C2 C3 C11 C16 . . 2.9(4)
C2 C3 C11 C12 . . -176.8(3)
C16 C11 C12 C13 . . -1.3(4)
C3 C11 C12 C13 . . 178.4(2)
C16 C11 C12 O1 . 2_766 164.17(19)
C3 C11 C12 O1 . 2_766 -16.1(2)
C11 C12 C13 C14 . . 0.2(4)
O1 C12 C13 C14 2_766 . -158.1(2)
C11 C12 C13 F1 . . -178.9(2)
O1 C12 C13 F1 2_766 . 22.9(4)
C12 C13 C14 C15 . . 0.7(4)
F1 C13 C14 C15 . . 179.7(2)
C13 C14 C15 F2 . . -179.5(2)
C13 C14 C15 C16 . . -0.3(4)
F2 C15 C16 C11 . . 178.4(2)
C14 C15 C16 C11 . . -0.9(4)
C12 C11 C16 C15 . . 1.7(4)
C3 C11 C16 C15 . . -178.0(2)
O1 C1 C21 C26 . . -3.7(4)
C2 C1 C21 C26 . . 175.7(2)
O1 C1 C21 C22 . . 176.6(3)
C2 C1 C21 C22 . . -4.0(4)
C26 C21 C22 C23 . . 0.3(4)
C1 C21 C22 C23 . . 180.0(3)
C21 C22 C23 C24 . . -0.4(5)
C22 C23 C24 C25 . . -0.1(5)
C23 C24 C25 C26 . . 0.7(5)
C22 C21 C26 C25 . . 0.4(4)
C1 C21 C26 C25 . . -179.3(3)
C24 C25 C26 C21 . . -0.9(5)
