#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:58:33 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202018 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/25/8102546.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8102546
loop_
_publ_author_name
'Ai-Yun Wang'
'Lei Shi'
'Hai-Liang Zhu'
_publ_section_title
;
 Crystal structure of
 (E)-2-fluoro-6-((4-hydroxyphenethylimino)methyl)phenol, C15H14FNO2
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              531
_journal_volume                  224
_journal_year                    2009
_chemical_formula_moiety         'C15 H14 F N O2'
_chemical_formula_sum            'C15 H14 F N O2'
_chemical_formula_weight         259.27
_chemical_name_systematic
;        
(E)-2-fluoro-6-((4-hydroxyphenethylimino)methyl)phenol
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                68.52(3)
_cell_angle_beta                 74.05(3)
_cell_angle_gamma                83.07(3)
_cell_formula_units_Z            2
_cell_length_a                   7.5568(14)
_cell_length_b                   9.465(2)
_cell_length_c                   10.1088(19)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     646.8(3)
_computing_cell_refinement       'CAD4 software'
_computing_data_collection       'CAD4 software (Enraf-Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXL-97(Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'ω/2θ 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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0203
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2536
_diffrn_reflns_theta_full        25.97
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_min         2.24
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9759
_exptl_absorpt_correction_T_min  0.9712
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'North et al. (1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2536
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0464
_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)+(0.0612P)²+0.2647P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1162
_refine_ls_wR_factor_ref         0.1520
_reflns_number_gt                1931
_reflns_number_total             2536
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            1267-2759.cff
_cod_data_source_block           I
_cod_original_cell_volume        646.8(2)
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               8102546
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2620(3) 0.3647(2) 0.9962(2) 0.0433(5) Uani 1 2 i d . . .
C2 C 0.2105(3) 0.3052(2) 0.9013(2) 0.0452(5) Uani 1 2 i d . . .
C3 C 0.2207(3) 0.1448(3) 0.9436(3) 0.0556(6) Uani 1 2 i d . . .
C4 C 0.2731(4) 0.0522(3) 1.0647(3) 0.0635(7) Uani 1 2 i d . . .
H4 H 0.2772 -0.0524 1.0870 0.076 Uiso 1 2 i calc R . .
C5 C 0.3212(4) 0.1127(3) 1.1568(3) 0.0655(7) Uani 1 2 i d . . .
H5 H 0.3576 0.0489 1.2402 0.079 Uiso 1 2 i calc R . .
C6 C 0.3139(3) 0.2668(3) 1.1229(2) 0.0567(6) Uani 1 2 i d . . .
H6 H 0.3439 0.3073 1.1848 0.068 Uiso 1 2 i calc R . .
C7 C 0.2581(3) 0.5245(2) 0.9612(2) 0.0452(5) Uani 1 2 i d . . .
H7 H 0.2876 0.5626 1.0250 0.054 Uiso 1 2 i calc R . .
C8 C 0.2055(3) 0.7839(2) 0.8025(2) 0.0529(6) Uani 1 2 i d . . .
H8A H 0.2535 0.8137 0.8679 0.063 Uiso 1 2 i calc R . .
H8B H 0.0780 0.8184 0.8116 0.063 Uiso 1 2 i calc R . .
C9 C 0.3156(4) 0.8582(3) 0.6453(2) 0.0594(6) Uani 1 2 i d . . .
H9A H 0.2887 0.9665 0.6140 0.071 Uiso 1 2 i calc R . .
H9B H 0.4458 0.8435 0.6419 0.071 Uiso 1 2 i calc R . .
C10 C 0.2746(3) 0.7956(2) 0.5393(2) 0.0501(5) Uani 1 2 i d . . .
C11 C 0.4111(3) 0.7246(3) 0.4617(3) 0.0575(6) Uani 1 2 i d . . .
H11 H 0.5303 0.7183 0.4728 0.069 Uiso 1 2 i calc R . .
C12 C 0.3746(3) 0.6627(3) 0.3681(3) 0.0617(6) Uani 1 2 i d . . .
H12 H 0.4688 0.6152 0.3172 0.074 Uiso 1 2 i calc R . .
C13 C 0.1996(3) 0.6713(3) 0.3499(2) 0.0562(6) Uani 1 2 i d . . .
C14 C 0.0595(3) 0.7399(3) 0.4270(3) 0.0592(6) Uani 1 2 i d . . .
H14 H -0.0596 0.7451 0.4160 0.071 Uiso 1 2 i calc R . .
C15 C 0.0981(3) 0.8010(3) 0.5209(3) 0.0570(6) Uani 1 2 i d . . .
H15 H 0.0034 0.8470 0.5730 0.068 Uiso 1 2 i calc R . .
F1 F 0.1726(3) 0.08550(17) 0.85569(19) 0.0883(6) Uani 1 2 i d . . .
N1 N 0.2155(2) 0.61862(19) 0.84506(18) 0.0453(4) Uani 1 2 i d D . .
H2 H 0.181(3) 0.575(3) 0.788(2) 0.054 Uiso 1 2 i d D . .
O1 O 0.1720(3) 0.6108(3) 0.2538(2) 0.0834(6) Uani 1 2 i d D . .
H1 H 0.061(3) 0.616(5) 0.252(4) 0.125 Uiso 1 2 i d D . .
O2 O 0.1604(2) 0.38962(17) 0.78526(17) 0.0567(4) Uani 1 2 i d . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C7 120.48(19) . . ?
C6 C1 C2 120.58(19) . . ?
C7 C1 C2 118.94(18) . . ?
O2 C2 C3 121.9(2) . . ?
O2 C2 C1 122.97(18) . . ?
C3 C2 C1 115.1(2) . . ?
C4 C3 F1 120.0(2) . . ?
C4 C3 C2 123.6(2) . . ?
F1 C3 C2 116.3(2) . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 119.2(2) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 121.1(2) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
N1 C7 C1 122.76(19) . . ?
N1 C7 H7 118.6 . . ?
C1 C7 H7 118.6 . . ?
N1 C8 C9 110.71(18) . . ?
N1 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C10 C9 C8 113.12(18) . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C15 117.4(2) . . ?
C11 C10 C9 120.8(2) . . ?
C15 C10 C9 121.7(2) . . ?
C12 C11 C10 121.5(2) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C13 C12 C11 120.1(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
O1 C13 C12 117.7(2) . . ?
O1 C13 C14 122.4(2) . . ?
C12 C13 C14 119.9(2) . . ?
C13 C14 C15 119.3(2) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C14 C15 C10 121.8(2) . . ?
C14 C15 H15 119.1 . . ?
C10 C15 H15 119.1 . . ?
C7 N1 C8 126.07(18) . . ?
C7 N1 H2 115.3(15) . . ?
C8 N1 H2 118.5(15) . . ?
C13 O1 H1 112(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.405(3) . ?
C1 C7 1.420(3) . ?
C1 C2 1.430(3) . ?
C2 O2 1.282(3) . ?
C2 C3 1.417(3) . ?
C3 C4 1.349(4) . ?
C3 F1 1.353(3) . ?
C4 C5 1.398(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.369(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.283(3) . ?
C7 H7 0.9300 . ?
C8 N1 1.461(3) . ?
C8 C9 1.520(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.511(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.380(3) . ?
C10 C15 1.389(3) . ?
C11 C12 1.379(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.374(3) . ?
C12 H12 0.9300 . ?
C13 O1 1.364(3) . ?
C13 C14 1.379(3) . ?
C14 C15 1.384(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
N1 H2 0.920(16) . ?
O1 H1 0.842(18) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H2 O2 0.920(16) 1.79(2) 2.560(2) 139(2) .
O1 H1 O2 0.842(18) 1.82(2) 2.648(3) 167(4) 2_566
C7 H7 O1 0.93 2.43 3.229(3) 144.5 1_556
C8 H8A F1 0.97 2.54 3.063(3) 114.0 1_565
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 O2 179.3(2) . . . . ?
C7 C1 C2 O2 -0.1(3) . . . . ?
C6 C1 C2 C3 -1.4(3) . . . . ?
C7 C1 C2 C3 179.23(19) . . . . ?
O2 C2 C3 C4 179.9(2) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
O2 C2 C3 F1 -0.7(3) . . . . ?
C1 C2 C3 F1 179.96(19) . . . . ?
F1 C3 C4 C5 -179.3(2) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C1 -1.0(4) . . . . ?
C7 C1 C6 C5 -179.0(2) . . . . ?
C2 C1 C6 C5 1.7(3) . . . . ?
C6 C1 C7 N1 178.4(2) . . . . ?
C2 C1 C7 N1 -2.2(3) . . . . ?
N1 C8 C9 C10 48.3(3) . . . . ?
C8 C9 C10 C11 -118.5(2) . . . . ?
C8 C9 C10 C15 58.6(3) . . . . ?
C15 C10 C11 C12 0.7(3) . . . . ?
C9 C10 C11 C12 177.9(2) . . . . ?
C10 C11 C12 C13 0.2(4) . . . . ?
C11 C12 C13 O1 178.7(2) . . . . ?
C11 C12 C13 C14 -0.9(4) . . . . ?
O1 C13 C14 C15 -178.9(2) . . . . ?
C12 C13 C14 C15 0.7(4) . . . . ?
C13 C14 C15 C10 0.2(4) . . . . ?
C11 C10 C15 C14 -0.9(3) . . . . ?
C9 C10 C15 C14 -178.1(2) . . . . ?
C1 C7 N1 C8 179.0(2) . . . . ?
C9 C8 N1 C7 129.2(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653973
