#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/51/2205197.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_2205197
loop_
_publ_author_name
'Wei Zhou'
'Weixiao Hu'
'Luping Lv'
'Chunnian Xia'
_publ_section_title
;
 10-(4-Fluorobenzylidene)anthrone
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o592
_journal_page_last               o593
_journal_paper_doi               10.1107/S1600536805002655
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C21 H13 F O'
_chemical_formula_moiety         'C21 H13 F O'
_chemical_formula_sum            'C21 H13 F O'
_chemical_formula_weight         300.31
_chemical_name_systematic
;
10-(4-Fluorobenzylidene)anthrone
;
_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
_cell_angle_beta                 109.79(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.044(6)
_cell_length_b                   11.398(3)
_cell_length_c                   13.820(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      12.67
_cell_measurement_theta_min      11.14
_cell_volume                     1488.7(11)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo 1995)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Version 1.05; Farrugia, 1999)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0115
_diffrn_reflns_av_sigmaI/netI    0.0148
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3137
_diffrn_reflns_theta_full        25.17
_diffrn_reflns_theta_max         25.17
_diffrn_reflns_theta_min         2.15
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.139
_refine_ls_extinction_coef       0.0058(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2673
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0333
_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)+(0.0525P)²+0.247P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.1032
_reflns_number_gt                2026
_reflns_number_total             2673
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ac6156.cif
_cod_data_source_block           I
_cod_original_cell_volume        1488.7(10)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2205197
_cod_database_fobs_code          2205197
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_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_type_symbol
F1 0.46323(12) 1.13505(10) 0.22408(10) 0.0977(4) Uani d . 1 F
O1 0.04833(13) 0.33472(9) 0.13091(9) 0.0663(3) Uani d . 1 O
C1 -0.21168(17) 0.43485(14) 0.01400(11) 0.0580(4) Uani d . 1 C
H1 -0.2023 0.3541 0.0092 0.070 Uiso calc R 1 H
C2 -0.33601(18) 0.48835(17) -0.04179(13) 0.0685(5) Uani d . 1 C
H2 -0.4111 0.4442 -0.0841 0.082 Uiso calc R 1 H
C3 -0.34915(17) 0.60847(17) -0.03479(13) 0.0670(5) Uani d . 1 C
H3 -0.4344 0.6447 -0.0711 0.080 Uiso calc R 1 H
C4 -0.23743(15) 0.67491(15) 0.02528(11) 0.0569(4) Uani d . 1 C
H4 -0.2474 0.7559 0.0278 0.068 Uiso calc R 1 H
C5 0.01670(14) 0.69201(12) 0.14295(10) 0.0440(3) Uani d . 1 C
C6 0.20273(15) 0.68760(14) 0.31943(10) 0.0522(4) Uani d . 1 C
H6 0.1967 0.7688 0.3236 0.063 Uiso calc R 1 H
C7 0.29415(16) 0.62594(16) 0.40089(11) 0.0614(4) Uani d . 1 C
H7 0.3481 0.6658 0.4598 0.074 Uiso calc R 1 H
C8 0.30632(17) 0.50583(16) 0.39572(12) 0.0637(4) Uani d . 1 C
H8 0.3696 0.4651 0.4504 0.076 Uiso calc R 1 H
C9 0.22484(16) 0.44651(14) 0.30976(12) 0.0555(4) Uani d . 1 C
H9 0.2334 0.3655 0.3061 0.067 Uiso calc R 1 H
C10 0.03015(15) 0.43892(13) 0.14268(10) 0.0481(3) Uani d . 1 C
C11 -0.09878(15) 0.50051(13) 0.07809(10) 0.0469(3) Uani d . 1 C
C12 0.12921(14) 0.50705(13) 0.22794(10) 0.0464(3) Uani d . 1 C
C13 0.11917(14) 0.62930(12) 0.23078(10) 0.0440(3) Uani d . 1 C
C14 -0.10890(14) 0.62261(13) 0.08273(10) 0.0458(3) Uani d . 1 C
C15 0.03268(14) 0.80040(13) 0.11125(10) 0.0484(3) Uani d . 1 C
H15 -0.0457 0.8274 0.0579 0.058 Uiso calc R 1 H
C16 0.14984(15) 0.88502(12) 0.14427(10) 0.0465(3) Uani d . 1 C
C17 0.11758(15) 1.00391(13) 0.13936(11) 0.0518(4) Uani d . 1 C
H17 0.0232 1.0269 0.1168 0.062 Uiso calc R 1 H
C18 0.22135(18) 1.08850(14) 0.16698(12) 0.0610(4) Uani d . 1 C
H18 0.1984 1.1677 0.1651 0.073 Uiso calc R 1 H
C19 0.35952(18) 1.05237(15) 0.19737(13) 0.0632(4) Uani d . 1 C
C20 0.39741(17) 0.93670(15) 0.20095(13) 0.0620(4) Uani d . 1 C
H20 0.4921 0.9150 0.2209 0.074 Uiso calc R 1 H
C21 0.29226(15) 0.85320(13) 0.17435(11) 0.0528(4) Uani d . 1 C
H21 0.3165 0.7743 0.1765 0.063 Uiso calc R 1 H
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
_geom_angle_publ_flag
C2 C1 C11 120.56(16) ?
C2 C1 H1 119.7 ?
C11 C1 H1 119.7 ?
C1 C2 C3 119.50(15) ?
C1 C2 H2 120.2 ?
C3 C2 H2 120.2 ?
C4 C3 C2 120.67(16) ?
C4 C3 H3 119.7 ?
C2 C3 H3 119.7 ?
C3 C4 C14 121.03(16) ?
C3 C4 H4 119.5 ?
C14 C4 H4 119.5 ?
C15 C5 C13 125.88(13) yes
C15 C5 C14 118.82(12) yes
C13 C5 C14 115.17(12) ?
C7 C6 C13 120.63(15) ?
C7 C6 H6 119.7 ?
C13 C6 H6 119.7 ?
C8 C7 C6 120.64(15) ?
C8 C7 H7 119.7 ?
C6 C7 H7 119.7 ?
C9 C8 C7 119.82(15) ?
C9 C8 H8 120.1 ?
C7 C8 H8 120.1 ?
C8 C9 C12 120.27(15) ?
C8 C9 H9 119.9 ?
C12 C9 H9 119.9 ?
O1 C10 C11 121.44(14) yes
O1 C10 C12 121.76(14) yes
C11 C10 C12 116.57(13) ?
C1 C11 C14 120.42(14) ?
C1 C11 C10 119.07(14) ?
C14 C11 C10 120.50(13) ?
C9 C12 C13 120.47(14) ?
C9 C12 C10 118.65(13) ?
C13 C12 C10 120.66(13) ?
C6 C13 C12 118.10(13) ?
C6 C13 C5 122.23(13) ?
C12 C13 C5 119.61(12) ?
C11 C14 C4 117.73(13) ?
C11 C14 C5 119.69(13) ?
C4 C14 C5 122.51(14) ?
C5 C15 C16 132.55(13) ?
C5 C15 H15 113.7 ?
C16 C15 H15 113.7 ?
C17 C16 C21 117.81(14) ?
C17 C16 C15 118.41(13) yes
C21 C16 C15 123.65(13) yes
C18 C17 C16 121.85(14) ?
C18 C17 H17 119.1 ?
C16 C17 H17 119.1 ?
C19 C18 C17 117.91(15) ?
C19 C18 H18 121.0 ?
C17 C18 H18 121.0 ?
F1 C19 C20 118.67(16) ?
F1 C19 C18 118.57(16) ?
C20 C19 C18 122.76(15) ?
C19 C20 C21 118.54(15) ?
C19 C20 H20 120.7 ?
C21 C20 H20 120.7 ?
C20 C21 C16 121.09(15) ?
C20 C21 H21 119.5 ?
C16 C21 H21 119.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C19 1.3598(19) yes
O1 C10 1.2209(17) yes
C1 C2 1.369(2) ?
C1 C11 1.397(2) ?
C1 H1 0.9300 ?
C2 C3 1.382(3) ?
C2 H2 0.9300 ?
C3 C4 1.375(2) ?
C3 H3 0.9300 ?
C4 C14 1.399(2) ?
C4 H4 0.9300 ?
C5 C15 1.338(2) yes
C5 C13 1.4824(19) ?
C5 C14 1.483(2) ?
C6 C7 1.380(2) ?
C6 C13 1.397(2) ?
C6 H6 0.9300 ?
C7 C8 1.378(2) ?
C7 H7 0.9300 ?
C8 C9 1.371(2) ?
C8 H8 0.9300 ?
C9 C12 1.394(2) ?
C9 H9 0.9300 ?
C10 C11 1.478(2) ?
C10 C12 1.479(2) ?
C11 C14 1.398(2) ?
C12 C13 1.399(2) ?
C15 C16 1.470(2) yes
C15 H15 0.9300 ?
C16 C17 1.390(2) ?
C16 C21 1.396(2) ?
C17 C18 1.376(2) ?
C17 H17 0.9300 ?
C18 C19 1.370(3) ?
C18 H18 0.9300 ?
C19 C20 1.368(2) ?
C20 C21 1.376(2) ?
C20 H20 0.9300 ?
C21 H21 0.9300 ?
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
_geom_torsion_publ_flag
C11 C1 C2 C3 0.3(3) ?
C1 C2 C3 C4 1.9(3) ?
C2 C3 C4 C14 -1.6(3) ?
C13 C6 C7 C8 1.0(2) ?
C6 C7 C8 C9 -1.4(3) ?
C7 C8 C9 C12 -0.4(2) ?
C2 C1 C11 C14 -2.9(2) ?
C2 C1 C11 C10 175.75(14) ?
O1 C10 C11 C1 10.5(2) ?
C12 C10 C11 C1 -164.17(13) ?
O1 C10 C11 C14 -170.94(13) ?
C12 C10 C11 C14 14.44(19) ?
C8 C9 C12 C13 2.5(2) ?
C8 C9 C12 C10 -172.10(14) ?
O1 C10 C12 C9 -15.5(2) ?
C11 C10 C12 C9 159.09(13) ?
O1 C10 C12 C13 169.87(13) ?
C11 C10 C12 C13 -15.52(19) ?
C7 C6 C13 C12 1.1(2) ?
C7 C6 C13 C5 178.16(13) ?
C9 C12 C13 C6 -2.8(2) ?
C10 C12 C13 C6 171.68(13) ?
C9 C12 C13 C5 -179.97(13) ?
C10 C12 C13 C5 -5.46(19) ?
C15 C5 C13 C6 34.1(2) ?
C14 C5 C13 C6 -150.10(13) ?
C15 C5 C13 C12 -148.89(14) ?
C14 C5 C13 C12 26.92(18) ?
C1 C11 C14 C4 3.1(2) ?
C10 C11 C14 C4 -175.50(13) ?
C1 C11 C14 C5 -173.86(13) ?
C10 C11 C14 C5 7.55(19) ?
C3 C4 C14 C11 -0.9(2) ?
C3 C4 C14 C5 175.94(14) ?
C15 C5 C14 C11 148.10(14) ?
C13 C5 C14 C11 -28.02(18) ?
C15 C5 C14 C4 -28.7(2) ?
C13 C5 C14 C4 155.18(13) ?
C13 C5 C15 C16 4.4(2) yes
C14 C5 C15 C16 -171.30(14) yes
C5 C15 C16 C17 -146.85(16) yes
C5 C15 C16 C21 37.3(2) yes
C21 C16 C17 C18 -2.6(2) ?
C15 C16 C17 C18 -178.71(14) ?
C16 C17 C18 C19 1.7(2) ?
C17 C18 C19 F1 179.46(14) ?
C17 C18 C19 C20 0.1(3) ?
F1 C19 C20 C21 179.70(14) ?
C18 C19 C20 C21 -1.0(3) ?
C19 C20 C21 C16 0.0(2) ?
C17 C16 C21 C20 1.7(2) ?
C15 C16 C21 C20 177.59(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21129902
