#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/05/2210538.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_2210538
loop_
_publ_author_name
'Temel, Ersin'
'Albayrak, Çiĝdem'
'Büyükgüngör, Orhan'
'Odabaşoğlu, Mustafa'
_publ_section_title
;
 Zwitterionic
 (E)-2-hydroxy-6-[(o-tolyliminio)methyl]phenolate
 0.07-hydrate
;
_journal_coeditor_code           CI2154
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4484
_journal_page_last               o4486
_journal_paper_doi               10.1107/S1600536806036774
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C14 H13 N O2, 0.07H2 O'
_chemical_formula_moiety         'C14 H13 N O2, 0.07H2 O'
_chemical_formula_sum            'C14 H13.14 N O2.07'
_chemical_formula_weight         228.52
_chemical_melting_point          384.5(5)
_chemical_name_systematic
;
(E)-2-hydroxy-6-[(o-tolyliminio)methyl]phenolate 0.07-hydrate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 107.135(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.9334(14)
_cell_length_b                   7.2265(5)
_cell_length_c                   13.9798(10)
_cell_measurement_reflns_used    16009
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.29
_cell_measurement_theta_min      2.66
_cell_volume                     2310.6(3)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Stoe IPDS-2'
_diffrn_measurement_method       ω
_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  0.0910
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17777
_diffrn_reflns_theta_full        27.26
_diffrn_reflns_theta_max         27.26
_diffrn_reflns_theta_min         2.96
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9753
_exptl_absorpt_correction_T_min  0.9451
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             966
_exptl_crystal_size_max          0.74
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.174
_refine_ls_extinction_coef       0.0019(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2571
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0515
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.12P)²+0.2796P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1365
_refine_ls_wR_factor_ref         0.1474
_reflns_number_gt                1917
_reflns_number_total             2571
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2154.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '384-385' was changed to '384.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '384-385' was changed to '384.5(5)' -
the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2210538
_cod_database_fobs_code          2210538
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
C C1 0.49961(6) 0.4542(2) 0.12132(9) 0.0564(4) Uani d . 1
C C2 0.51704(6) 0.2776(2) 0.09788(10) 0.0584(4) Uani d . 1
C C3 0.57502(7) 0.2563(3) 0.09266(11) 0.0700(5) Uani d . 1
C C4 0.61333(7) 0.4015(3) 0.11587(12) 0.0775(5) Uani d . 1
H H4 0.6518 0.3841 0.1156 0.093 Uiso calc R 1
C C5 0.59593(8) 0.5740(3) 0.13977(12) 0.0772(5) Uani d . 1
H H5 0.6226 0.6710 0.1548 0.093 Uiso calc R 1
C C6 0.53988(7) 0.6022(3) 0.14133(11) 0.0673(4) Uani d . 1
H H6 0.5282 0.7191 0.1556 0.081 Uiso calc R 1
C C7 0.44178(6) 0.4820(2) 0.12575(9) 0.0549(4) Uani d . 1
H H7 0.4306 0.6001 0.1392 0.066 Uiso calc R 1
C C8 0.34574(6) 0.3702(2) 0.11492(9) 0.0512(3) Uani d . 1
C C9 0.31695(7) 0.5377(2) 0.09384(11) 0.0618(4) Uani d . 1
H H9 0.3356 0.6389 0.0756 0.074 Uiso calc R 1
C C10 0.26080(8) 0.5555(3) 0.09968(13) 0.0737(5) Uani d . 1
H H10 0.2417 0.6689 0.0864 0.088 Uiso calc R 1
C C11 0.23302(8) 0.4056(3) 0.12511(14) 0.0767(5) Uani d . 1
H H11 0.1951 0.4172 0.1294 0.092 Uiso calc R 1
C C12 0.26123(8) 0.2389(3) 0.14413(13) 0.0723(5) Uani d . 1
H H12 0.2417 0.1379 0.1605 0.087 Uiso calc R 1
C C13 0.31800(7) 0.2156(2) 0.13976(10) 0.0584(4) Uani d . 1
C C14 0.34870(9) 0.0330(2) 0.16143(15) 0.0791(5) Uani d . 1
H H14A 0.3234 -0.0560 0.1785 0.119 Uiso calc R 1
H H14B 0.3837 0.0465 0.2164 0.119 Uiso calc R 1
H H14C 0.3587 -0.0084 0.1033 0.119 Uiso calc R 1
N N1 0.40398(5) 0.34905(17) 0.11179(8) 0.0538(3) Uani d D 1
H H1 0.4212(11) 0.243(2) 0.0977(19) 0.142(10) Uiso d D 1
O O1 0.48180(5) 0.13363(16) 0.07991(9) 0.0681(3) Uani d . 1
O O2 0.59204(6) 0.0894(3) 0.06620(12) 0.0950(5) Uani d . 1
H H2 0.5634(14) 0.016(5) 0.032(2) 0.148(12) Uiso d . 1
O O3 0.5000 0.9181(18) 0.2500 0.083(4) Uani d SP 0.14
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0536(8) 0.0719(9) 0.0444(6) -0.0061(7) 0.0154(5) 0.0025(6)
C2 0.0503(8) 0.0769(10) 0.0491(7) -0.0004(7) 0.0163(6) 0.0051(6)
C3 0.0528(9) 0.0978(13) 0.0599(8) 0.0073(8) 0.0175(7) 0.0043(8)
C4 0.0464(9) 0.1247(17) 0.0609(9) -0.0053(9) 0.0151(7) 0.0064(9)
C5 0.0621(10) 0.1081(15) 0.0602(8) -0.0267(10) 0.0161(7) 0.0011(9)
C6 0.0653(10) 0.0817(11) 0.0549(8) -0.0150(8) 0.0176(7) 0.0002(7)
C7 0.0593(9) 0.0581(8) 0.0491(7) -0.0014(7) 0.0189(6) -0.0019(6)
C8 0.0511(8) 0.0570(8) 0.0472(6) -0.0031(6) 0.0170(5) -0.0060(5)
C9 0.0615(9) 0.0583(9) 0.0692(9) 0.0003(7) 0.0250(7) -0.0011(7)
C10 0.0635(10) 0.0788(11) 0.0808(10) 0.0127(8) 0.0243(8) -0.0039(8)
C11 0.0564(9) 0.0979(14) 0.0812(11) -0.0009(9) 0.0284(8) -0.0056(9)
C12 0.0638(10) 0.0823(12) 0.0765(10) -0.0182(9) 0.0293(8) -0.0033(8)
C13 0.0616(9) 0.0619(9) 0.0536(7) -0.0083(7) 0.0201(6) -0.0056(6)
C14 0.0898(13) 0.0602(10) 0.0929(12) -0.0083(9) 0.0358(10) 0.0041(8)
N1 0.0544(7) 0.0573(7) 0.0532(6) -0.0003(6) 0.0213(5) -0.0020(5)
O1 0.0618(7) 0.0667(7) 0.0808(7) 0.0019(5) 0.0289(5) -0.0032(5)
O2 0.0580(8) 0.1184(12) 0.1093(10) 0.0143(8) 0.0260(7) -0.0173(9)
O3 0.125(13) 0.052(7) 0.081(8) 0.000 0.043(8) 0.000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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 C6 120.01(14)
C2 C1 C7 119.87(13)
C6 C1 C7 120.12(15)
O1 C2 C1 122.86(13)
O1 C2 C3 119.08(15)
C1 C2 C3 118.06(14)
O2 C3 C4 120.75(16)
O2 C3 C2 119.08(16)
C4 C3 C2 120.15(17)
C3 C4 C5 121.24(16)
C3 C4 H4 119.4
C5 C4 H4 119.4
C6 C5 C4 120.36(17)
C6 C5 H5 119.8
C4 C5 H5 119.8
C5 C6 C1 120.05(18)
C5 C6 H6 120.0
C1 C6 H6 120.0
N1 C7 C1 122.39(14)
N1 C7 H7 118.8
C1 C7 H7 118.8
C9 C8 C13 120.74(14)
C9 C8 N1 121.45(13)
C13 C8 N1 117.81(13)
C10 C9 C8 120.24(16)
C10 C9 H9 119.9
C8 C9 H9 119.9
C11 C10 C9 119.87(17)
C11 C10 H10 120.1
C9 C10 H10 120.1
C12 C11 C10 119.78(16)
C12 C11 H11 120.1
C10 C11 H11 120.1
C11 C12 C13 122.11(16)
C11 C12 H12 118.9
C13 C12 H12 118.9
C12 C13 C8 117.23(15)
C12 C13 C14 121.77(15)
C8 C13 C14 121.00(14)
C13 C14 H14A 109.5
C13 C14 H14B 109.5
H14A C14 H14B 109.5
C13 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C7 N1 C8 124.48(13)
C7 N1 H1 108.2(18)
C8 N1 H1 127.3(18)
C3 O2 H2 115(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.411(2)
C1 C6 1.412(2)
C1 C7 1.418(2)
C2 O1 1.3160(19)
C2 C3 1.419(2)
C3 O2 1.359(2)
C3 C4 1.368(3)
C4 C5 1.386(3)
C4 H4 0.93
C5 C6 1.363(3)
C5 H5 0.93
C6 H6 0.93
C7 N1 1.2946(19)
C7 H7 0.93
C8 C9 1.381(2)
C8 C13 1.395(2)
C8 N1 1.4157(19)
C9 C10 1.376(2)
C9 H9 0.93
C10 C11 1.372(3)
C10 H10 0.93
C11 C12 1.368(3)
C11 H11 0.93
C12 C13 1.388(2)
C12 H12 0.93
C13 C14 1.497(2)
C14 H14A 0.96
C14 H14B 0.96
C14 H14C 0.96
N1 H1 0.918(10)
O2 H2 0.89(3)
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 H2 O1 5_655 0.89(3) 1.95(3) 2.787(2) 157(3)
N1 H1 O1 . 0.918(10) 1.733(17) 2.5651(16) 149(3)
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
C6 C1 C2 O1 179.02(13)
C7 C1 C2 O1 -0.3(2)
C6 C1 C2 C3 -1.6(2)
C7 C1 C2 C3 179.02(12)
O1 C2 C3 O2 2.0(2)
C1 C2 C3 O2 -177.33(14)
O1 C2 C3 C4 -176.75(14)
C1 C2 C3 C4 3.9(2)
O2 C3 C4 C5 177.86(16)
C2 C3 C4 C5 -3.4(2)
C3 C4 C5 C6 0.5(3)
C4 C5 C6 C1 1.8(2)
C2 C1 C6 C5 -1.2(2)
C7 C1 C6 C5 178.18(13)
C2 C1 C7 N1 2.0(2)
C6 C1 C7 N1 -177.29(13)
C13 C8 C9 C10 1.7(2)
N1 C8 C9 C10 -178.50(14)
C8 C9 C10 C11 -1.0(3)
C9 C10 C11 C12 -0.3(3)
C10 C11 C12 C13 0.8(3)
C11 C12 C13 C8 0.0(2)
C11 C12 C13 C14 179.54(16)
C9 C8 C13 C12 -1.2(2)
N1 C8 C13 C12 179.00(12)
C9 C8 C13 C14 179.23(14)
N1 C8 C13 C14 -0.6(2)
C1 C7 N1 C8 -179.65(12)
C9 C8 N1 C7 26.2(2)
C13 C8 N1 C7 -154.06(13)
