#------------------------------------------------------------------------------
#$Date: 2016-02-21 11:56:54 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176809 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/05/2240553.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_2240553
loop_
_publ_author_name
'Shalini, Suresh'
'Girija, C. R.'
'Jotani, Mukesh M.'
'Sathish, C. D.'
'Venkatesha, T. V.'
_publ_section_title
;
 Crystal structure of
 2-{(E)-[(2-hydroxyphenyl)iminiumyl]methyl}-4-methylphenolate
;
_journal_coeditor_code           HB7370
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o288
_journal_paper_doi               10.1107/S2056989015006374
_journal_volume                  71
_journal_year                    2015
_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_melting_point          355
_chemical_name_common            N-(5-methylsalicylidene)aniline
_chemical_name_systematic
;
2-{(E)-[(2-Hydroxyphenyl)iminiumyl]methyl}-4-methylphenolate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.9474(18)
_cell_length_b                   9.0660(13)
_cell_length_c                   19.583(3)
_cell_measurement_reflns_used    500
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      50.0
_cell_measurement_theta_min      5.0
_cell_volume                     2298.7(6)
_computing_cell_refinement
;
SAINT (Bruker, 2009)
;
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_data_reduction
;
SAINT (Bruker, 2009)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       OMEGA-PHI
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            29481
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.550
_diffrn_reflns_theta_min         2.608
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2009)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.201
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2583
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0498
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0467P)²+1.0454P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1298
_reflns_number_gt                1810
_reflns_number_total             2583
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7370sup1.cf
_cod_data_source_block           I
_cod_database_code               2240553
_cod_database_fobs_code          2240553
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, 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_occupancy
H H1 0.6541(13) 0.138(3) 0.2650(11) 0.063(7) Uiso d 1
H H4 0.5002(18) 0.378(3) 0.1982(14) 0.099(9) Uiso d 1
N N1 0.71804(10) 0.16956(16) 0.25537(7) 0.0328(3) Uani d 1
C C8 0.78912(12) 0.1022(2) 0.29051(8) 0.0345(4) Uani d 1
H H8 0.8579 0.1254 0.2819 0.041 Uiso calc 1
O O1 0.58630(9) 0.00525(16) 0.31990(7) 0.0465(4) Uani d 1
C C9 0.73191(11) 0.2767(2) 0.20440(8) 0.0315(4) Uani d 1
O O2 0.55197(9) 0.31121(17) 0.20963(7) 0.0494(4) Uani d 1
C C14 0.64308(12) 0.3480(2) 0.18036(9) 0.0350(4) Uani d 1
C C5 0.66350(13) -0.0477(2) 0.35492(9) 0.0358(4) Uani d 1
C C10 0.82779(13) 0.3143(2) 0.17751(9) 0.0389(4) Uani d 1
H H10 0.8872 0.2685 0.1937 0.047 Uiso calc 1
C C4 0.76708(12) -0.0042(2) 0.34097(8) 0.0335(4) Uani d 1
C C2 0.83378(15) -0.1684(2) 0.42880(10) 0.0451(5) Uani d 1
C C13 0.65167(14) 0.4516(2) 0.12897(9) 0.0415(5) Uani d 1
H H13 0.5928 0.4982 0.1124 0.050 Uiso calc 1
C C6 0.64951(14) -0.1513(2) 0.40786(9) 0.0441(5) Uani d 1
H H6 0.5830 -0.1815 0.4191 0.053 Uiso calc 1
C C11 0.83474(14) 0.4189(2) 0.12694(10) 0.0462(5) Uani d 1
H H11 0.8990 0.4445 0.1094 0.055 Uiso calc 1
C C3 0.84905(13) -0.0673(2) 0.37804(9) 0.0418(5) Uani d 1
H H3 0.9163 -0.0390 0.3676 0.050 Uiso calc 1
C C7 0.73159(15) -0.2085(2) 0.44311(9) 0.0461(5) Uani d 1
H H7 0.7190 -0.2763 0.4778 0.055 Uiso calc 1
C C12 0.74692(16) 0.4864(2) 0.10209(9) 0.0457(5) Uani d 1
H H12 0.7520 0.5554 0.0671 0.055 Uiso calc 1
C C1 0.92146(18) -0.2371(3) 0.46830(12) 0.0691(7) Uani d 1
H H1A 0.9742 -0.2687 0.4372 0.104 Uiso calc 1
H H1B 0.8963 -0.3205 0.4935 0.104 Uiso calc 1
H H1C 0.9497 -0.1658 0.4994 0.104 Uiso calc 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
C8 N1 C9 127.59(14)
C8 N1 H1 113.3(15)
C9 N1 H1 119.1(15)
N1 C8 C4 123.26(15)
N1 C8 H8 118.4
C4 C8 H8 118.4
C10 C9 C14 119.50(16)
C10 C9 N1 123.55(15)
C14 C9 N1 116.95(14)
C14 O2 H4 111.4(18)
O2 C14 C13 123.12(15)
O2 C14 C9 117.36(16)
C13 C14 C9 119.52(15)
O1 C5 C6 122.24(16)
O1 C5 C4 121.25(16)
C6 C5 C4 116.51(16)
C11 C10 C9 120.02(16)
C11 C10 H10 120.0
C9 C10 H10 120.0
C3 C4 C8 119.13(15)
C3 C4 C5 119.91(16)
C8 C4 C5 120.96(15)
C3 C2 C7 117.15(17)
C3 C2 C1 122.77(18)
C7 C2 C1 120.08(18)
C12 C13 C14 120.40(17)
C12 C13 H13 119.8
C14 C13 H13 119.8
C7 C6 C5 121.52(17)
C7 C6 H6 119.2
C5 C6 H6 119.2
C10 C11 C12 120.41(17)
C10 C11 H11 119.8
C12 C11 H11 119.8
C2 C3 C4 122.59(17)
C2 C3 H3 118.7
C4 C3 H3 118.7
C6 C7 C2 122.30(18)
C6 C7 H7 118.9
C2 C7 H7 118.9
C13 C12 C11 120.12(18)
C13 C12 H12 119.9
C11 C12 H12 119.9
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
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C8 1.301(2)
N1 C9 1.404(2)
N1 H1 0.895(16)
C8 C4 1.410(2)
C8 H8 0.9300
O1 C5 1.304(2)
C9 C10 1.391(2)
C9 C14 1.401(2)
O2 C14 1.353(2)
O2 H4 0.932(17)
C14 C13 1.381(3)
C5 C6 1.410(3)
C5 C4 1.424(2)
C10 C11 1.374(3)
C10 H10 0.9300
C4 C3 1.407(2)
C2 C3 1.367(3)
C2 C7 1.400(3)
C2 C1 1.508(3)
C13 C12 1.377(3)
C13 H13 0.9300
C6 C7 1.369(3)
C6 H6 0.9300
C11 C12 1.380(3)
C11 H11 0.9300
C3 H3 0.9300
C7 H7 0.9300
C12 H12 0.9300
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
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 H4 O1 3_655 0.932(17) 1.645(17) 2.5756(18) 176(3)
N1 H1 O2 . 0.896(18) 2.32(2) 2.6598(19) 102.2(19)
N1 H1 O1 . 0.896(18) 1.84(2) 2.5933(19) 141(2)
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
C9 N1 C8 C4 179.90(16)
C8 N1 C9 C10 8.4(3)
C8 N1 C9 C14 -171.45(17)
C10 C9 C14 O2 -177.89(16)
N1 C9 C14 O2 2.0(2)
C10 C9 C14 C13 1.8(3)
N1 C9 C14 C13 -178.31(16)
C14 C9 C10 C11 -1.1(3)
N1 C9 C10 C11 179.06(17)
N1 C8 C4 C3 -177.72(17)
N1 C8 C4 C5 2.0(3)
O1 C5 C4 C3 -177.76(17)
C6 C5 C4 C3 1.7(3)
O1 C5 C4 C8 2.5(3)
C6 C5 C4 C8 -177.99(17)
O2 C14 C13 C12 178.77(18)
C9 C14 C13 C12 -0.9(3)
O1 C5 C6 C7 178.47(18)
C4 C5 C6 C7 -1.0(3)
C9 C10 C11 C12 -0.6(3)
C7 C2 C3 C4 0.1(3)
C1 C2 C3 C4 179.5(2)
C8 C4 C3 C2 178.41(19)
C5 C4 C3 C2 -1.3(3)
C5 C6 C7 C2 -0.2(3)
C3 C2 C7 C6 0.7(3)
C1 C2 C7 C6 -178.8(2)
C14 C13 C12 C11 -0.8(3)
C10 C11 C12 C13 1.5(3)
