#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/40/2234079.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_2234079
loop_
_publ_author_name
'Jothi, L.'
'Vasuki, G.'
'Babu, R. Ramesh'
'Ramamurthi, K.'
_publ_section_title
;
 4-[(E)-(4-Methylphenyl)iminomethyl]phenol
;
_journal_coeditor_code           ZS2179
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o897
_journal_paper_doi               10.1107/S1600536812007635
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C14 H13 N O'
_chemical_formula_moiety         'C14 H13 N O'
_chemical_formula_sum            'C14 H13 N O'
_chemical_formula_weight         211.25
_chemical_name_systematic
;
4-[(E)-(4-Methylphenyl)iminomethyl]phenol
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.6180(10)
_cell_length_b                   11.0561(6)
_cell_length_c                   9.3318(5)
_cell_measurement_reflns_used    2333
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.26
_cell_measurement_theta_min      2.5
_cell_volume                     2230.4(2)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT and XPREP (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  '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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'ω and φ'
_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  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11344
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.01
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9843
_exptl_absorpt_correction_T_min  0.9766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.139
_refine_ls_extinction_coef       0.0028(10)
_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   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         1961
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0356
_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)+(0.0452P)²+0.5906P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0999
_reflns_number_gt                1559
_reflns_number_total             1961
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zs2179.cif
_cod_data_source_block           I
_cod_database_code               2234079
_cod_database_fobs_code          2234079
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, 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_symmetry_multiplicity
C C1 0.98404(9) -0.3138(2) 0.5166(2) 0.0696(6) Uani d . 1 1
H H1A 1.0178 -0.2713 0.5605 0.104 Uiso calc R 1 1
H H1B 0.9999 -0.3738 0.4519 0.104 Uiso calc R 1 1
H H1C 0.9597 -0.3525 0.5894 0.104 Uiso calc R 1 1
C C2 0.94434(7) -0.22573(15) 0.43514(19) 0.0463(4) Uani d . 1 1
C C3 0.93867(8) -0.10700(16) 0.47974(19) 0.0480(4) Uani d . 1 1
H H3 0.9599 -0.0814 0.5610 0.058 Uiso calc R 1 1
C C4 0.90213(7) -0.02566(14) 0.40601(18) 0.0424(4) Uani d . 1 1
H H4 0.9001 0.0544 0.4363 0.051 Uiso calc R 1 1
C C5 0.86863(7) -0.06207(13) 0.28760(16) 0.0344(4) Uani d . 1 1
C C6 0.87510(8) -0.18013(14) 0.23975(18) 0.0425(4) Uani d . 1 1
H H6 0.8543 -0.2055 0.1578 0.051 Uiso calc R 1 1
C C7 0.91231(8) -0.25992(15) 0.31352(19) 0.0484(5) Uani d . 1 1
H H7 0.9160 -0.3390 0.2805 0.058 Uiso calc R 1 1
C C8 0.78057(7) -0.01218(13) 0.15734(16) 0.0364(4) Uani d . 1 1
H H8 0.7683 -0.0915 0.1744 0.044 Uiso calc R 1 1
C C9 0.74169(7) 0.06129(13) 0.06518(16) 0.0343(4) Uani d . 1 1
C C10 0.76120(7) 0.17174(13) 0.00844(16) 0.0348(4) Uani d . 1 1
H H10 0.7993 0.2033 0.0359 0.042 Uiso calc R 1 1
C C11 0.72512(7) 0.23468(12) -0.08724(16) 0.0350(4) Uani d . 1 1
H H11 0.7389 0.3083 -0.1234 0.042 Uiso calc R 1 1
C C12 0.66836(7) 0.18910(13) -0.13011(16) 0.0344(4) Uani d . 1 1
C C13 0.64808(7) 0.07966(13) -0.07395(18) 0.0407(4) Uani d . 1 1
H H13 0.6099 0.0486 -0.1011 0.049 Uiso calc R 1 1
C C14 0.68428(7) 0.01724(13) 0.02146(18) 0.0402(4) Uani d . 1 1
H H14 0.6702 -0.0561 0.0578 0.048 Uiso calc R 1 1
N N1 0.83053(6) 0.02412(11) 0.21682(13) 0.0350(3) Uani d . 1 1
O O1 0.63156(5) 0.24423(10) -0.22698(13) 0.0457(3) Uani d . 1 1
H H1 0.6475 0.3149 -0.2500 0.055 Uiso calc R 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C7 C2 C3 117.54(15)
C7 C2 C1 121.59(17)
C3 C2 C1 120.87(17)
C4 C3 C2 121.28(16)
C4 C3 H3 119.4
C2 C3 H3 119.4
C3 C4 C5 120.58(15)
C3 C4 H4 119.7
C5 C4 H4 119.7
C4 C5 C6 118.63(14)
C4 C5 N1 118.68(13)
C6 C5 N1 122.66(14)
C7 C6 C5 120.04(16)
C7 C6 H6 120.0
C5 C6 H6 120.0
C6 C7 C2 121.84(16)
C6 C7 H7 119.1
C2 C7 H7 119.1
N1 C8 C9 124.80(14)
N1 C8 H8 117.6
C9 C8 H8 117.6
C14 C9 C10 117.61(14)
C14 C9 C8 119.57(13)
C10 C9 C8 122.63(13)
C11 C10 C9 121.17(13)
C11 C10 H10 119.4
C9 C10 H10 119.4
C10 C11 C12 120.39(14)
C10 C11 H11 119.8
C12 C11 H11 119.8
O1 C12 C11 123.45(14)
O1 C12 C13 117.38(13)
C11 C12 C13 119.16(14)
C14 C13 C12 120.19(14)
C14 C13 H13 119.9
C12 C13 H13 119.9
C13 C14 C9 121.47(14)
C13 C14 H14 119.3
C9 C14 H14 119.3
C8 N1 C5 118.71(13)
C12 O1 H1 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.504(2)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 C7 1.382(2)
C2 C3 1.383(2)
C3 C4 1.381(2)
C3 H3 0.9300
C4 C5 1.381(2)
C4 H4 0.9300
C5 C6 1.387(2)
C5 N1 1.4221(19)
C6 C7 1.378(2)
C6 H6 0.9300
C7 H7 0.9300
C8 N1 1.279(2)
C8 C9 1.451(2)
C8 H8 0.9300
C9 C14 1.394(2)
C9 C10 1.396(2)
C10 C11 1.375(2)
C10 H10 0.9300
C11 C12 1.386(2)
C11 H11 0.9300
C12 O1 1.3496(18)
C12 C13 1.390(2)
C13 C14 1.372(2)
C13 H13 0.9300
C14 H14 0.9300
O1 H1 0.8811
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_654 0.88 1.87 2.7397(17) 170
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
C7 C2 C3 C4 0.3(3)
C1 C2 C3 C4 -179.72(16)
C2 C3 C4 C5 2.0(2)
C3 C4 C5 C6 -3.5(2)
C3 C4 C5 N1 178.62(14)
C4 C5 C6 C7 2.7(2)
N1 C5 C6 C7 -179.48(14)
C5 C6 C7 C2 -0.4(3)
C3 C2 C7 C6 -1.1(3)
C1 C2 C7 C6 178.95(17)
N1 C8 C9 C14 -171.69(15)
N1 C8 C9 C10 13.4(2)
C14 C9 C10 C11 -0.1(2)
C8 C9 C10 C11 174.95(14)
C9 C10 C11 C12 -0.3(2)
C10 C11 C12 O1 -177.82(13)
C10 C11 C12 C13 0.7(2)
O1 C12 C13 C14 177.90(14)
C11 C12 C13 C14 -0.7(2)
C12 C13 C14 C9 0.3(2)
C10 C9 C14 C13 0.1(2)
C8 C9 C14 C13 -175.12(14)
C9 C8 N1 C5 -171.11(13)
C4 C5 N1 C8 -147.79(14)
C6 C5 N1 C8 34.4(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12624759
