#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/65/2226525.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_2226525
loop_
_publ_author_name
'Zheng, Mei'
'Wang, Jianfeng'
'Zhang, Jixu'
'Luo, Shuping'
_publ_section_title
;
 3-Fluoro-4-(4-hydroxyphenoxy)benzonitrile
;
_journal_coeditor_code           IM2202
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1856
_journal_paper_doi               10.1107/S1600536810024360
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H8 F N O2'
_chemical_formula_moiety         'C13 H8 F N O2'
_chemical_formula_sum            'C13 H8 F N O2'
_chemical_formula_weight         229.20
_chemical_name_systematic
;
3-Fluoro-4-(4-hydroxyphenoxy)benzonitrile
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1932(4)
_cell_length_b                   8.8109(5)
_cell_length_c                   20.5269(12)
_cell_measurement_reflns_used    6842
_cell_measurement_temperature    295.0(10)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.0
_cell_volume                     1120.11(12)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 2006)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 2006)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2007)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia,1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295.0(10)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rolling anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10999
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9755
_exptl_absorpt_correction_T_min  0.9586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.147
_refine_ls_extinction_coef       0.031(5)
_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   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         1498
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0374
_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)+(0.0487P)²+0.2503P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.1170
_reflns_number_gt                928
_reflns_number_total             1498
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            im2202.cif
_cod_data_source_block           I
_cod_database_code               2226525
_cod_database_fobs_code          2226525
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.8260(4) 0.8262(3) 0.91021(10) 0.0842(7) Uani d . 1 . .
F F1 0.7477(4) 0.5751(2) 0.84401(10) 0.0994(7) Uani d . 1 . .
C C3 0.2965(5) 0.7967(4) 0.78841(13) 0.0647(8) Uani d . 1 . .
C C13 0.1155(6) 0.7849(4) 0.74589(16) 0.0797(10) Uani d . 1 . .
C C7 0.8277(5) 0.9255(4) 0.96363(13) 0.0662(8) Uani d . 1 . .
O O2 0.8846(4) 1.2010(3) 1.12504(11) 0.0890(8) Uani d . 1 . .
H H201 0.7775 1.1944 1.1484 0.134 Uiso calc R 1 . .
C C4 0.3341(5) 0.9302(4) 0.82157(14) 0.0706(8) Uani d . 1 . .
H H4 0.2411 1.0120 0.8158 0.085 Uiso calc R 1 . .
C C10 0.8605(5) 1.1076(3) 1.07184(13) 0.0647(8) Uani d . 1 . .
C C1 0.6082(5) 0.6918(4) 0.83712(14) 0.0689(8) Uani d . 1 . .
C C8 0.6707(5) 0.9204(4) 1.01045(14) 0.0720(8) Uani d . 1 . .
H H8 0.5543 0.8546 1.0059 0.086 Uiso calc R 1 . .
C C6 0.6460(5) 0.8233(4) 0.87182(13) 0.0648(8) Uani d . 1 . .
C C2 0.4369(5) 0.6748(4) 0.79642(14) 0.0712(8) Uani d . 1 . .
H H2 0.4141 0.5839 0.7744 0.085 Uiso calc R 1 . .
C C9 0.6853(5) 1.0130(4) 1.06440(14) 0.0718(9) Uani d . 1 . .
H H9 0.5769 1.0115 1.0958 0.086 Uiso calc R 1 . .
C C11 1.0188(6) 1.1111(4) 1.02514(15) 0.0789(10) Uani d . 1 . .
H H11 1.1376 1.1745 1.0301 0.095 Uiso calc R 1 . .
C C12 1.0011(6) 1.0202(4) 0.97087(15) 0.0805(10) Uani d . 1 . .
H H12 1.1076 1.0231 0.9390 0.097 Uiso calc R 1 . .
C C5 0.5080(6) 0.9438(4) 0.86314(14) 0.0710(9) Uani d . 1 . .
H H5 0.5319 1.0344 0.8853 0.085 Uiso calc R 1 . .
N N1 -0.0310(6) 0.7800(4) 0.71268(15) 0.1078(12) 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'
F F 0.0171 0.0103 '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'
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
C6 O1 C7 . . 118.0(2) ?
C4 C3 C2 . . 119.7(3) ?
C4 C3 C13 . . 119.8(3) ?
C2 C3 C13 . . 120.5(3) ?
N1 C13 C3 . . 177.8(5) ?
C12 C7 C8 . . 120.1(3) ?
C12 C7 O1 . . 118.1(3) ?
C8 C7 O1 . . 121.6(3) ?
C10 O2 H201 . . 109.5 ?
C5 C4 C3 . . 120.7(3) ?
C5 C4 H4 . . 119.6 ?
C3 C4 H4 . . 119.6 ?
C11 C10 O2 . . 117.7(3) ?
C11 C10 C9 . . 119.9(3) ?
O2 C10 C9 . . 122.4(3) ?
F1 C1 C2 . . 118.7(3) ?
F1 C1 C6 . . 118.5(3) ?
C2 C1 C6 . . 122.8(3) ?
C7 C8 C9 . . 119.9(3) ?
C7 C8 H8 . . 120.0 ?
C9 C8 H8 . . 120.0 ?
O1 C6 C5 . . 124.6(3) ?
O1 C6 C1 . . 116.9(3) ?
C5 C6 C1 . . 118.4(3) ?
C1 C2 C3 . . 118.4(3) ?
C1 C2 H2 . . 120.8 ?
C3 C2 H2 . . 120.8 ?
C10 C9 C8 . . 119.9(3) ?
C10 C9 H9 . . 120.0 ?
C8 C9 H9 . . 120.0 ?
C10 C11 C12 . . 119.7(3) ?
C10 C11 H11 . . 120.1 ?
C12 C11 H11 . . 120.1 ?
C7 C12 C11 . . 120.3(3) ?
C7 C12 H12 . . 119.8 ?
C11 C12 H12 . . 119.8 ?
C6 C5 C4 . . 119.9(3) ?
C6 C5 H5 . . 120.0 ?
C4 C5 H5 . . 120.0 ?
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
O1 C6 . 1.365(4) ?
O1 C7 . 1.403(4) ?
F1 C1 . 1.350(3) ?
C3 C4 . 1.379(5) ?
C3 C2 . 1.391(4) ?
C3 C13 . 1.425(4) ?
C13 N1 . 1.135(4) ?
C7 C12 . 1.368(5) ?
C7 C8 . 1.368(4) ?
O2 C10 . 1.375(3) ?
O2 H201 . 0.8200 ?
C4 C5 . 1.379(4) ?
C4 H4 . 0.9300 ?
C10 C11 . 1.371(4) ?
C10 C9 . 1.377(4) ?
C1 C2 . 1.359(4) ?
C1 C6 . 1.380(4) ?
C8 C9 . 1.378(4) ?
C8 H8 . 0.9300 ?
C6 C5 . 1.375(4) ?
C2 H2 . 0.9300 ?
C9 H9 . 0.9300 ?
C11 C12 . 1.376(4) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C5 H5 . 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
O2 H201 N1 2_575 0.82 2.03 2.839(4) 168
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 O1 C7 C12 . . . . -129.3(3) ?
C6 O1 C7 C8 . . . . 56.0(4) ?
C2 C3 C4 C5 . . . . -0.7(5) ?
C13 C3 C4 C5 . . . . 179.8(3) ?
C12 C7 C8 C9 . . . . 1.2(5) ?
O1 C7 C8 C9 . . . . 175.8(3) ?
C7 O1 C6 C5 . . . . 27.9(4) ?
C7 O1 C6 C1 . . . . -155.4(3) ?
F1 C1 C6 O1 . . . . 1.0(4) ?
C2 C1 C6 O1 . . . . -179.0(3) ?
F1 C1 C6 C5 . . . . 177.9(3) ?
C2 C1 C6 C5 . . . . -2.1(5) ?
F1 C1 C2 C3 . . . . -178.6(3) ?
C6 C1 C2 C3 . . . . 1.4(5) ?
C4 C3 C2 C1 . . . . 0.0(5) ?
C13 C3 C2 C1 . . . . 179.5(3) ?
C11 C10 C9 C8 . . . . 0.8(5) ?
O2 C10 C9 C8 . . . . -179.2(3) ?
C7 C8 C9 C10 . . . . -1.6(5) ?
O2 C10 C11 C12 . . . . -179.7(3) ?
C9 C10 C11 C12 . . . . 0.3(5) ?
C8 C7 C12 C11 . . . . -0.1(5) ?
O1 C7 C12 C11 . . . . -174.8(3) ?
C10 C11 C12 C7 . . . . -0.7(5) ?
O1 C6 C5 C4 . . . . 178.0(3) ?
C1 C6 C5 C4 . . . . 1.4(5) ?
C3 C4 C5 C6 . . . . 0.0(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 14578717
