#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/01/2220183.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_2220183
loop_
_publ_author_name
'Song, Xiao-Qing'
_publ_section_title
;
 1-(3,4-Dihydroxyphenyl)-2-(4-fluorophenyl)ethanone
;
_journal_coeditor_code           HB2831
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2282
_journal_paper_doi               10.1107/S1600536808035733
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C14 H11 F O3'
_chemical_formula_moiety         'C14 H11 F O3'
_chemical_formula_sum            'C14 H11 F O3'
_chemical_formula_weight         246.23
_chemical_name_systematic
;
1-(3,4-Dihydroxyphenyl)-2-(4-fluorophenyl)ethanone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 105.33(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1640(16)
_cell_length_b                   5.9120(12)
_cell_length_c                   24.946(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     1161.2(5)
_computing_cell_refinement       'CAD4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            2229
_diffrn_reflns_theta_full        25.21
_diffrn_reflns_theta_max         25.21
_diffrn_reflns_theta_min         1.69
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.172
_refine_ls_extinction_coef       0.019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2072
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0497
_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)+(0.0627P)²+0.5485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1454
_reflns_number_gt                1452
_reflns_number_total             2072
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2831.cif
_cod_data_source_block           I
_cod_original_cell_volume        1161.2(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2220183
_cod_database_fobs_code          2220183
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
C C1 0.5159(3) 0.4835(4) 0.08518(10) 0.0502(6) Uani d . 1
C C2 0.4714(3) 0.2980(4) 0.04986(10) 0.0536(7) Uani d . 1
H H2A 0.5544 0.2229 0.0374 0.064 Uiso calc R 1
C C3 0.3067(3) 0.2257(4) 0.03341(11) 0.0533(6) Uani d . 1
C C4 0.1810(3) 0.3396(4) 0.05140(10) 0.0496(6) Uani d . 1
C C5 0.2243(3) 0.5232(5) 0.08571(11) 0.0609(7) Uani d . 1
H H5A 0.1406 0.5990 0.0977 0.073 Uiso calc R 1
C C6 0.3901(3) 0.5969(5) 0.10269(12) 0.0622(8) Uani d . 1
H H6A 0.4177 0.7224 0.1258 0.075 Uiso calc R 1
C C7 0.6960(3) 0.5566(4) 0.10307(10) 0.0502(6) Uani d . 1
C C8 0.7428(3) 0.7480(5) 0.14453(12) 0.0636(8) Uani d . 1
H H8A 0.6923 0.8862 0.1266 0.076 Uiso calc R 1
H H8B 0.6923 0.7179 0.1749 0.076 Uiso calc R 1
C C9 0.9297(3) 0.7876(4) 0.16843(10) 0.0496(6) Uani d . 1
C C10 1.0273(3) 0.6323(4) 0.20441(11) 0.0543(7) Uani d . 1
H H10A 0.9768 0.5008 0.2129 0.065 Uiso calc R 1
C C11 1.1974(3) 0.6678(5) 0.22796(12) 0.0614(7) Uani d . 1
H H11A 1.2620 0.5620 0.2522 0.074 Uiso calc R 1
C C12 1.2691(3) 0.8598(5) 0.21518(13) 0.0640(8) Uani d . 1
C C13 1.1793(4) 1.0184(5) 0.17977(13) 0.0693(8) Uani d . 1
H H13A 1.2317 1.1486 0.1715 0.083 Uiso calc R 1
C C14 1.0083(4) 0.9806(5) 0.15645(12) 0.0624(7) Uani d . 1
H H14A 0.9450 1.0872 0.1322 0.075 Uiso calc R 1
F F1 1.4375(2) 0.8958(4) 0.23816(10) 0.1039(7) Uani d . 1
O O1 0.2648(2) 0.0477(4) -0.00250(10) 0.0813(7) Uani d . 1
H H1A 0.1726 -0.0035 -0.0012 0.122 Uiso calc R 1
O O2 0.0199(2) 0.2558(3) 0.03311(8) 0.0615(5) Uani d . 1
H H2B -0.0421 0.3199 0.0493 0.092 Uiso calc R 1
O O3 0.8048(2) 0.4626(3) 0.08579(8) 0.0650(6) 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'
F F 0.0171 0.0103 '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'
H H 0.0000 0.0000 '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
C6 C1 C2 119.2(2)
C6 C1 C7 121.4(2)
C2 C1 C7 119.4(2)
C3 C2 C1 120.5(2)
C3 C2 H2A 119.8
C1 C2 H2A 119.8
O1 C3 C2 119.6(2)
O1 C3 C4 120.3(2)
C2 C3 C4 120.1(2)
O2 C4 C5 124.3(2)
O2 C4 C3 116.2(2)
C5 C4 C3 119.5(2)
C4 C5 C6 120.9(2)
C4 C5 H5A 119.6
C6 C5 H5A 119.6
C5 C6 C1 119.9(3)
C5 C6 H6A 120.1
C1 C6 H6A 120.1
O3 C7 C1 121.2(2)
O3 C7 C8 120.5(2)
C1 C7 C8 118.3(2)
C9 C8 C7 115.7(2)
C9 C8 H8A 108.3
C7 C8 H8A 108.3
C9 C8 H8B 108.3
C7 C8 H8B 108.3
H8A C8 H8B 107.4
C14 C9 C10 118.0(2)
C14 C9 C8 121.6(2)
C10 C9 C8 120.3(2)
C11 C10 C9 121.4(2)
C11 C10 H10A 119.3
C9 C10 H10A 119.3
C12 C11 C10 118.6(3)
C12 C11 H11A 120.7
C10 C11 H11A 120.7
C11 C12 F1 119.0(3)
C11 C12 C13 122.6(3)
F1 C12 C13 118.5(3)
C12 C13 C14 118.2(3)
C12 C13 H13A 120.9
C14 C13 H13A 120.9
C9 C14 C13 121.2(3)
C9 C14 H14A 119.4
C13 C14 H14A 119.4
C3 O1 H1A 109.5
C4 O2 H2B 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.391(3)
C1 C2 1.393(3)
C1 C7 1.483(3)
C2 C3 1.366(3)
C2 H2A 0.9300
C3 O1 1.365(3)
C3 C4 1.397(3)
C4 O2 1.366(3)
C4 C5 1.369(4)
C5 C6 1.378(3)
C5 H5A 0.9300
C6 H6A 0.9300
C7 O3 1.219(3)
C7 C8 1.512(4)
C8 C9 1.503(3)
C8 H8A 0.9700
C8 H8B 0.9700
C9 C14 1.380(4)
C9 C10 1.380(3)
C10 C11 1.374(3)
C10 H10A 0.9300
C11 C12 1.354(4)
C11 H11A 0.9300
C12 F1 1.359(3)
C12 C13 1.362(4)
C13 C14 1.381(4)
C13 H13A 0.9300
C14 H14A 0.9300
O1 H1A 0.8200
O2 H2B 0.8200
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 H1A O2 . 0.82 2.28 2.690(2) 111
O1 H1A O2 3 0.82 2.16 2.876(3) 146
O2 H2B O3 1_455 0.82 1.92 2.744(2) 178
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 -1.2(4)
C7 C1 C2 C3 179.1(2)
C1 C2 C3 O1 178.1(2)
C1 C2 C3 C4 0.9(4)
O1 C3 C4 O2 2.9(4)
C2 C3 C4 O2 -179.9(2)
O1 C3 C4 C5 -177.5(3)
C2 C3 C4 C5 -0.3(4)
O2 C4 C5 C6 179.6(3)
C3 C4 C5 C6 0.0(4)
C4 C5 C6 C1 -0.4(4)
C2 C1 C6 C5 1.0(4)
C7 C1 C6 C5 -179.4(3)
C6 C1 C7 O3 -176.9(3)
C2 C1 C7 O3 2.8(4)
C6 C1 C7 C8 4.5(4)
C2 C1 C7 C8 -175.8(2)
O3 C7 C8 C9 -8.8(4)
C1 C7 C8 C9 169.9(2)
C7 C8 C9 C14 112.3(3)
C7 C8 C9 C10 -69.3(3)
C14 C9 C10 C11 0.3(4)
C8 C9 C10 C11 -178.2(2)
C9 C10 C11 C12 -0.1(4)
C10 C11 C12 F1 -179.8(3)
C10 C11 C12 C13 -0.3(4)
C11 C12 C13 C14 0.3(5)
F1 C12 C13 C14 179.9(3)
C10 C9 C14 C13 -0.2(4)
C8 C9 C14 C13 178.3(2)
C12 C13 C14 C9 -0.1(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24685015
