#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/97/2239759.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_2239759
loop_
_publ_author_name
'Jothi, L.'
'Anuradha, G.'
'Vasuki, G.'
'Babu, R. Ramesh'
'Ramamurthi, K.'
_publ_section_title
;
 4-Fluoro-N-(4-hydroxybenzylidene)aniline
;
_journal_coeditor_code           SJ5413
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o860
_journal_paper_doi               10.1107/S1600536814015153
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C13 H10 F N O'
_chemical_formula_moiety         'C13 H10 F N O'
_chemical_formula_sum            'C13 H10 F N O'
_chemical_formula_weight         215.22
_chemical_name_systematic
;
4-Fluoro-N-(4-hydroxybenzylidene)aniline
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 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                   11.0153(8)
_cell_length_b                   9.8596(7)
_cell_length_c                   9.5476(6)
_cell_measurement_reflns_used    7057
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.39
_cell_measurement_theta_min      1.85
_cell_volume                     1036.93(12)
_computing_cell_refinement       'APEX2 and SAINT-Plus (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2004)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material
;
WinGX (Farrugia, 2012) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scan'
_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  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6612
_diffrn_reflns_theta_full        23.39
_diffrn_reflns_theta_max         23.39
_diffrn_reflns_theta_min         2.77
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_correction_T_min  0.9706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1430
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0286
_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)+(0.0435P)²+0.1030P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0707
_refine_ls_wR_factor_ref         0.0779
_reflns_number_gt                1282
_reflns_number_total             1430
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5413sup1.cif
_cod_data_source_block           I
_cod_database_code               2239759
_cod_database_fobs_code          2239759
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -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
_atom_site_symmetry_multiplicity
C C1 0.43955(18) 0.3194(2) 0.3175(2) 0.0396(6) Uani d . 1 1
C C2 0.48448(17) 0.44366(19) 0.2735(3) 0.0385(5) Uani d . 1 1
H H2 0.5578 0.4754 0.3091 0.046 Uiso calc R 1 1
C C3 0.42173(17) 0.5198(2) 0.1781(3) 0.0385(5) Uani d . 1 1
H H3 0.4526 0.6034 0.1502 0.046 Uiso calc R 1 1
C C4 0.31198(18) 0.4740(2) 0.1219(2) 0.0366(5) Uani d . 1 1
C C5 0.26905(18) 0.3484(2) 0.1656(3) 0.0448(6) Uani d . 1 1
H H5 0.1963 0.3159 0.1295 0.054 Uiso calc R 1 1
C C6 0.33162(18) 0.2716(2) 0.2608(3) 0.0467(6) Uani d . 1 1
H H6 0.3018 0.1873 0.2875 0.056 Uiso calc R 1 1
C C7 0.23844(18) 0.5576(2) 0.0292(3) 0.0393(5) Uani d . 1 1
H H7 0.1598 0.5287 0.0100 0.047 Uiso calc R 1 1
C C8 0.18716(17) 0.7493(2) -0.1001(3) 0.0371(5) Uani d . 1 1
C C9 0.2246(2) 0.8203(2) -0.2169(3) 0.0462(6) Uani d . 1 1
H H9 0.3051 0.8148 -0.2457 0.055 Uiso calc R 1 1
C C10 0.1439(2) 0.8992(2) -0.2914(3) 0.0546(6) Uani d . 1 1
H H10 0.1687 0.9455 -0.3713 0.066 Uiso calc R 1 1
C C11 0.0271(2) 0.9080(2) -0.2453(3) 0.0561(7) Uani d . 1 1
C C12 -0.0118(2) 0.8445(3) -0.1267(3) 0.0554(7) Uani d . 1 1
H H12 -0.0913 0.8554 -0.0957 0.067 Uiso calc R 1 1
C C13 0.06838(18) 0.7641(2) -0.0534(3) 0.0470(6) Uani d . 1 1
H H13 0.0430 0.7196 0.0274 0.056 Uiso calc R 1 1
N N1 0.27379(14) 0.66729(17) -0.02753(19) 0.0379(4) Uani d . 1 1
O O1 0.49408(13) 0.24314(15) 0.41734(19) 0.0509(4) Uani d . 1 1
H H1 0.5637 0.2701 0.4294 0.076 Uiso calc R 1 1
F F1 -0.05262(16) 0.98467(18) -0.3178(2) 0.0888(6) Uani d . 1 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 C1 C2 123.07(19)
O1 C1 C6 117.74(19)
C2 C1 C6 119.2(2)
C3 C2 C1 120.44(19)
C3 C2 H2 119.8
C1 C2 H2 119.8
C2 C3 C4 121.00(19)
C2 C3 H3 119.5
C4 C3 H3 119.5
C5 C4 C3 117.9(2)
C5 C4 C7 119.87(18)
C3 C4 C7 122.09(18)
C6 C5 C4 121.40(19)
C6 C5 H5 119.3
C4 C5 H5 119.3
C5 C6 C1 120.1(2)
C5 C6 H6 119.9
C1 C6 H6 119.9
N1 C7 C4 124.80(18)
N1 C7 H7 117.6
C4 C7 H7 117.6
C9 C8 C13 119.2(2)
C9 C8 N1 118.62(18)
C13 C8 N1 122.1(2)
C10 C9 C8 120.7(2)
C10 C9 H9 119.7
C8 C9 H9 119.7
C11 C10 C9 118.6(2)
C11 C10 H10 120.7
C9 C10 H10 120.7
F1 C11 C10 119.0(3)
F1 C11 C12 118.6(2)
C10 C11 C12 122.4(2)
C11 C12 C13 119.0(2)
C11 C12 H12 120.5
C13 C12 H12 120.5
C12 C13 C8 120.1(2)
C12 C13 H13 120.0
C8 C13 H13 120.0
C7 N1 C8 118.89(16)
C1 O1 H1 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.355(3)
C1 C2 1.386(3)
C1 C6 1.389(3)
C2 C3 1.368(3)
C2 H2 0.9300
C3 C4 1.398(3)
C3 H3 0.9300
C4 C5 1.389(3)
C4 C7 1.456(3)
C5 C6 1.369(3)
C5 H5 0.9300
C6 H6 0.9300
C7 N1 1.270(3)
C7 H7 0.9300
C8 C9 1.379(3)
C8 C13 1.390(3)
C8 N1 1.430(3)
C9 C10 1.379(3)
C9 H9 0.9300
C10 C11 1.362(3)
C10 H10 0.9300
C11 F1 1.350(3)
C11 C12 1.363(4)
C12 C13 1.378(3)
C12 H12 0.9300
C13 H13 0.9300
O1 H1 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 H1 N1 2_665 0.82 1.94 2.756(2) 175.8
C9 H9 F1 4_575 0.93 2.614 3.263(3) 127.3
C13 H13 Cg 4_465 0.93 2.83 3.710(3) 157
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
O1 C1 C2 C3 -176.2(2)
C6 C1 C2 C3 1.7(3)
C1 C2 C3 C4 -0.7(3)
C2 C3 C4 C5 -0.3(3)
C2 C3 C4 C7 174.8(2)
C3 C4 C5 C6 0.1(3)
C7 C4 C5 C6 -175.1(2)
C4 C5 C6 C1 1.0(4)
O1 C1 C6 C5 176.2(2)
C2 C1 C6 C5 -1.9(3)
C5 C4 C7 N1 -172.8(2)
C3 C4 C7 N1 12.2(3)
C13 C8 C9 C10 -3.6(3)
N1 C8 C9 C10 179.1(2)
C8 C9 C10 C11 1.5(3)
C9 C10 C11 F1 -179.8(2)
C9 C10 C11 C12 1.7(4)
F1 C11 C12 C13 178.8(2)
C10 C11 C12 C13 -2.6(4)
C11 C12 C13 C8 0.4(4)
C9 C8 C13 C12 2.6(3)
N1 C8 C13 C12 179.8(2)
C4 C7 N1 C8 -171.2(2)
C9 C8 N1 C7 -145.9(2)
C13 C8 N1 C7 36.9(3)
