#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/52/2235260.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_2235260
loop_
_publ_author_name
'Mohamed, Shaaban K.'
'Abdelhamid, Antar A.'
'Akkurt, Mehmet'
'Fanwick, Phillip E.'
'Maharramov, A. M.'
_publ_section_title
;
 2-((E)-{[4-(Hydroxymethyl)phenyl]imino}methyl)phenol
;
_journal_coeditor_code           TK5090
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1618
_journal_paper_doi               10.1107/S1600536812019368
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C14 H13 N O2'
_chemical_formula_moiety         'C14 H13 N O2'
_chemical_formula_sum            'C14 H13 N O2'
_chemical_formula_weight         227.25
_chemical_name_systematic
;
2-((E)-{[4-(Hydroxymethyl)phenyl]imino}methyl)phenol
;
_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
_cell_angle_alpha                90
_cell_angle_beta                 104.005(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.8172(14)
_cell_length_b                   4.72170(10)
_cell_length_c                   12.3106(2)
_cell_measurement_reflns_used    11657
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      66
_cell_measurement_theta_min      2
_cell_volume                     1117.67(9)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2001)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2001)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2001)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.0(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku RAPID II'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'confocal optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0212
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10711
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        66.58
_diffrn_reflns_theta_max         66.58
_diffrn_reflns_theta_min         4.60
_exptl_absorpt_coefficient_mu    0.733
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2001)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.182
_refine_ls_extinction_coef       0.0077(8)
_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   1.135
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0369
_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)+(0.0585P)²+0.1700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1073
_reflns_number_gt                1641
_reflns_number_total             1958
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk5090.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2235260
_cod_database_fobs_code          2235260
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.46733(5) 0.1618(2) 0.25819(8) 0.0330(3) Uani d . 1.000
O O2 0.19567(6) 1.2380(2) 0.56950(8) 0.0408(4) Uani d . 1.000
N N1 0.24780(5) 0.9636(2) 0.42590(9) 0.0258(3) Uani d . 1.000
C C1 0.44786(7) 0.1429(3) 0.36158(11) 0.0285(4) Uani d . 1.000
C C2 0.39457(6) 0.3581(3) 0.37420(11) 0.0252(4) Uani d . 1.000
C C3 0.34633(7) 0.4685(3) 0.28219(11) 0.0278(4) Uani d . 1.000
C C4 0.29742(7) 0.6676(3) 0.29556(11) 0.0279(4) Uani d . 1.000
C C5 0.29508(6) 0.7592(3) 0.40265(11) 0.0245(4) Uani d . 1.000
C C6 0.34194(7) 0.6431(3) 0.49448(11) 0.0279(4) Uani d . 1.000
C C7 0.39100(7) 0.4468(3) 0.48021(11) 0.0287(4) Uani d . 1.000
C C8 0.20820(6) 1.1083(3) 0.34759(11) 0.0257(4) Uani d . 1.000
C C9 0.15921(6) 1.3145(3) 0.37087(11) 0.0259(4) Uani d . 1.000
C C10 0.11604(6) 1.4634(3) 0.28242(11) 0.0296(4) Uani d . 1.000
C C11 0.06849(7) 1.6600(3) 0.30125(13) 0.0340(4) Uani d . 1.000
C C12 0.06377(7) 1.7098(3) 0.41032(13) 0.0371(5) Uani d . 1.000
C C13 0.10585(7) 1.5687(3) 0.49924(12) 0.0375(5) Uani d . 1.000
C C14 0.15422(7) 1.3713(3) 0.48079(11) 0.0299(4) Uani d . 1.000
H H1 0.4926(14) 0.330(5) 0.259(2) 0.099(8) Uiso d . 1.000
H H1A 0.48990 0.16730 0.42350 0.0340 Uiso c R 1.000
H H1B 0.42910 -0.04890 0.36840 0.0340 Uiso c R 1.000
H H2 0.2230(10) 1.115(5) 0.5393(17) 0.071(6) Uiso d . 1.000
H H3 0.34690 0.40630 0.20900 0.0330 Uiso c R 1.000
H H4 0.26540 0.74190 0.23170 0.0330 Uiso c R 1.000
H H6 0.34030 0.69910 0.56790 0.0340 Uiso c R 1.000
H H7 0.42280 0.37140 0.54410 0.0340 Uiso c R 1.000
H H8 0.21100 1.07970 0.27240 0.0310 Uiso c R 1.000
H H10 0.11950 1.42860 0.20800 0.0360 Uiso c R 1.000
H H11 0.03950 1.75950 0.24050 0.0410 Uiso c R 1.000
H H12 0.03090 1.84360 0.42380 0.0440 Uiso c R 1.000
H H13 0.10190 1.60590 0.57330 0.0450 Uiso c R 1.000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 ' 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 0.0311 0.0180 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 ' 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
C1 O1 H1 107.7(15) no
C14 O2 H2 105.4(13) no
C5 N1 C8 121.56(11) no
O1 C1 C2 113.65(11) no
C1 C2 C7 119.92(12) no
C3 C2 C7 118.02(12) no
C1 C2 C3 122.03(12) no
C2 C3 C4 121.19(12) no
C3 C4 C5 120.29(12) no
N1 C5 C4 124.99(12) no
C4 C5 C6 118.46(12) no
N1 C5 C6 116.56(12) no
C5 C6 C7 120.80(12) no
C2 C7 C6 121.20(12) no
N1 C8 C9 121.70(12) no
C10 C9 C14 118.72(12) no
C8 C9 C10 119.68(12) no
C8 C9 C14 121.60(12) no
C9 C10 C11 121.33(13) no
C10 C11 C12 118.97(13) no
C11 C12 C13 121.15(13) no
C12 C13 C14 120.12(13) no
C9 C14 C13 119.70(13) no
O2 C14 C9 121.19(12) no
O2 C14 C13 119.12(12) no
O1 C1 H1A 109.00 no
O1 C1 H1B 109.00 no
C2 C1 H1A 109.00 no
C2 C1 H1B 109.00 no
H1A C1 H1B 108.00 no
C2 C3 H3 119.00 no
C4 C3 H3 119.00 no
C3 C4 H4 120.00 no
C5 C4 H4 120.00 no
C5 C6 H6 120.00 no
C7 C6 H6 120.00 no
C2 C7 H7 119.00 no
C6 C7 H7 119.00 no
N1 C8 H8 119.00 no
C9 C8 H8 119.00 no
C9 C10 H10 119.00 no
C11 C10 H10 119.00 no
C10 C11 H11 120.00 no
C12 C11 H11 121.00 no
C11 C12 H12 119.00 no
C13 C12 H12 119.00 no
C12 C13 H13 120.00 no
C14 C13 H13 120.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.4193(17) no
O2 C14 1.3525(17) no
O1 H1 0.94(3) no
O2 H2 0.93(2) no
N1 C5 1.4216(17) no
N1 C8 1.2829(17) no
C1 C2 1.5004(19) no
C2 C7 1.3886(19) no
C2 C3 1.3945(19) no
C3 C4 1.388(2) no
C4 C5 1.3989(19) no
C5 C6 1.3902(19) no
C6 C7 1.385(2) no
C8 C9 1.4516(19) no
C9 C14 1.4063(19) no
C9 C10 1.4003(19) no
C10 C11 1.382(2) no
C11 C12 1.388(2) no
C12 C13 1.377(2) no
C13 C14 1.395(2) no
C1 H1A 0.9900 no
C1 H1B 0.9900 no
C3 H3 0.9500 no
C4 H4 0.9500 no
C6 H6 0.9500 no
C7 H7 0.9500 no
C8 H8 0.9500 no
C10 H10 0.9500 no
C11 H11 0.9500 no
C12 H12 0.9500 no
C13 H13 0.9500 no
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
_geom_hbond_publ_flag
O1 H1 O1 2_655 0.94(3) 1.79(2) 2.7235(14) 172(2) yes
O2 H2 N1 . 0.93(2) 1.74(2) 2.5990(15) 151.7(19) yes
C7 H7 O1 4_555 0.95 2.57 3.4288(16) 150 yes
C8 H8 O2 4_574 0.95 2.59 3.4492(16) 151 yes
C1 H1B Cg1 1_545 0.99 2.56 3.5050(15) 160 yes
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
C5 N1 C8 C9 179.17(12) no
C8 N1 C5 C4 -8.8(2) no
C8 N1 C5 C6 171.49(12) no
O1 C1 C2 C7 -153.49(12) no
O1 C1 C2 C3 28.42(18) no
C3 C2 C7 C6 -1.2(2) no
C1 C2 C3 C4 -179.98(14) no
C1 C2 C7 C6 -179.38(13) no
C7 C2 C3 C4 1.9(2) no
C2 C3 C4 C5 -0.8(2) no
C3 C4 C5 C6 -1.0(2) no
C3 C4 C5 N1 179.32(13) no
C4 C5 C6 C7 1.7(2) no
N1 C5 C6 C7 -178.61(12) no
C5 C6 C7 C2 -0.6(2) no
N1 C8 C9 C10 -178.71(12) no
N1 C8 C9 C14 1.8(2) no
C8 C9 C10 C11 179.61(13) no
C14 C9 C10 C11 -0.9(2) no
C8 C9 C14 O2 0.9(2) no
C8 C9 C14 C13 -179.25(13) no
C10 C9 C14 O2 -178.60(12) no
C10 C9 C14 C13 1.3(2) no
C9 C10 C11 C12 0.0(2) no
C10 C11 C12 C13 0.5(2) no
C11 C12 C13 C14 -0.1(2) no
C12 C13 C14 O2 179.11(13) no
C12 C13 C14 C9 -0.8(2) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657826
