#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/56/2235627.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_2235627
loop_
_publ_author_name
'Ortegon-Reyna, David'
'Garcias-Morales, Cesar'
'García-Báez, Efren V.'
'Ariza-Castolo, Armando'
'Martínez-Martínez, Francisco J.'
_publ_section_title
;
 (E)-4-Hydroxy-2-{[(2-phenylethyl)iminiumyl]methyl}phenolate
;
_journal_coeditor_code           SU2447
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2075
_journal_paper_doi               10.1107/S1600536812025408
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C15 H15 N O2'
_chemical_formula_moiety         'C15 H15 N O2'
_chemical_formula_sum            'C15 H15 N O2'
_chemical_formula_weight         241.28
_chemical_name_systematic
;
(E)-4-Hydroxy-2-{[(2-phenylethyl)iminiumyl]methyl}phenolate
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 124.81(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5010(19)
_cell_length_b                   12.936(3)
_cell_length_c                   12.551(4)
_cell_measurement_reflns_used    14042
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.91
_cell_volume                     1266.5(6)
_computing_cell_refinement       'HKL SCALEPACK (Otwinowski & Minor 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction
'HKL DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      170(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15718
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         4.13
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.8623
_exptl_absorpt_correction_T_min  0.8614
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
(Dwiggins, 1975)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.224
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2773
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0412
_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)+(0.0502P)²+0.3688P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1066
_reflns_number_gt                2367
_reflns_number_total             2773
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            su2447.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2235627
_cod_database_fobs_code          2235627
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_occupancy
_atom_site_disorder_group
O O1 0.88467(11) 0.43206(6) 0.61806(8) 0.0320(3) Uani 1.000 -16
O O4 0.99566(15) 0.00918(7) 0.64559(9) 0.0460(3) Uani 1.000 -16
N N8 0.75925(13) 0.42202(8) 0.37321(9) 0.0284(3) Uani 1.000 -16
C C1 0.90916(14) 0.33115(8) 0.62390(11) 0.0245(3) Uani 1.000 -16
C C2 0.85954(14) 0.27185(8) 0.51050(10) 0.0241(3) Uani 1.000 -16
C C3 0.88858(15) 0.16354(9) 0.51983(11) 0.0272(3) Uani 1.000 -16
C C4 0.96636(16) 0.11344(9) 0.63837(11) 0.0290(3) Uani 1.000 -16
C C5 1.01496(15) 0.17148(9) 0.75028(11) 0.0288(3) Uani 1.000 -16
C C6 0.98611(15) 0.27637(9) 0.74326(11) 0.0276(3) Uani 1.000 -16
C C7 0.78312(14) 0.32274(9) 0.38709(11) 0.0256(3) Uani 1.000 -16
C C9 0.68816(16) 0.47659(9) 0.24949(12) 0.0325(4) Uani 1.000 -16
C C10 0.52322(16) 0.53653(10) 0.20739(13) 0.0364(4) Uani 1.000 -16
C C11 0.55332(15) 0.62068(9) 0.30222(11) 0.0314(3) Uani 1.000 -16
C C12 0.48187(17) 0.61459(12) 0.37397(13) 0.0408(4) Uani 1.000 -16
C C13 0.51032(18) 0.69276(14) 0.46060(14) 0.0495(5) Uani 1.000 -16
C C14 0.60966(18) 0.77808(13) 0.47683(14) 0.0470(5) Uani 1.000 -16
C C15 0.68349(17) 0.78487(10) 0.40787(13) 0.0399(4) Uani 1.000 -16
C C16 0.65511(16) 0.70707(10) 0.32130(12) 0.0332(4) Uani 1.000 -16
H H3 0.85445 0.12504 0.44421 0.0326 Uiso 1.000 -16
H H4 1.03190 -0.01141 0.71879 0.0689 Uiso 1.000 -16
H H5 1.06841 0.13740 0.83162 0.0345 Uiso 1.000 -16
H H6 1.01819 0.31299 0.81963 0.0332 Uiso 1.000 -16
H H7 0.74885 0.28207 0.31297 0.0307 Uiso 1.000 -16
H H8 0.78653 0.45796 0.44009 0.0341 Uiso 1.000 -16
H H9A 0.66198 0.42590 0.18137 0.0389 Uiso 1.000 -16
H H9B 0.77472 0.52552 0.25890 0.0389 Uiso 1.000 -16
H H10A 0.47519 0.56802 0.12123 0.0437 Uiso 1.000 -16
H H10B 0.43734 0.48727 0.19847 0.0437 Uiso 1.000 -16
H H12 0.41353 0.55663 0.36330 0.0490 Uiso 1.000 -16
H H13 0.46162 0.68769 0.50873 0.0594 Uiso 1.000 -16
H H14 0.62724 0.83176 0.53491 0.0565 Uiso 1.000 -16
H H15 0.75308 0.84257 0.42000 0.0479 Uiso 1.000 -16
H H16 0.70530 0.71235 0.27424 0.0398 Uiso 1.000 -16
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
_geom_angle_publ_flag
C4 O4 H4 109.00 no
C7 N8 C9 123.74(10) no
C9 N8 H8 118.00 no
C7 N8 H8 118.00 no
O1 C1 C2 121.62(10) no
O1 C1 C6 121.22(10) no
C2 C1 C6 117.17(10) no
C1 C2 C7 119.95(10) no
C1 C2 C3 120.40(10) no
C3 C2 C7 119.64(10) no
C2 C3 C4 120.59(11) no
O4 C4 C3 119.65(11) no
C3 C4 C5 119.21(11) no
O4 C4 C5 121.14(10) no
C4 C5 C6 121.21(11) no
C1 C6 C5 121.41(11) no
N8 C7 C2 122.58(11) no
N8 C9 C10 111.47(13) no
C9 C10 C11 113.07(12) no
C10 C11 C12 121.30(13) no
C10 C11 C16 120.53(14) no
C12 C11 C16 118.18(12) no
C11 C12 C13 120.64(15) no
C12 C13 C14 120.24(17) no
C13 C14 C15 119.97(15) no
C14 C15 C16 119.87(15) no
C11 C16 C15 121.08(15) no
C2 C3 H3 120.00 no
C4 C3 H3 120.00 no
C4 C5 H5 119.00 no
C6 C5 H5 119.00 no
C1 C6 H6 119.00 no
C5 C6 H6 119.00 no
N8 C7 H7 119.00 no
C2 C7 H7 119.00 no
N8 C9 H9A 109.00 no
N8 C9 H9B 109.00 no
C10 C9 H9A 109.00 no
C10 C9 H9B 109.00 no
H9A C9 H9B 108.00 no
C9 C10 H10A 109.00 no
C9 C10 H10B 109.00 no
C11 C10 H10A 109.00 no
C11 C10 H10B 109.00 no
H10A C10 H10B 108.00 no
C11 C12 H12 120.00 no
C13 C12 H12 120.00 no
C12 C13 H13 120.00 no
C14 C13 H13 120.00 no
C13 C14 H14 120.00 no
C15 C14 H14 120.00 no
C14 C15 H15 120.00 no
C16 C15 H15 120.00 no
C11 C16 H16 119.00 no
C15 C16 H16 119.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.3206(14) no
O4 C4 1.3696(16) no
O4 H4 0.8200 no
N8 C7 1.2985(16) no
N8 C9 1.4725(16) no
N8 H8 0.8600 no
C1 C6 1.4250(17) no
C1 C2 1.4389(16) no
C2 C7 1.4407(16) no
C2 C3 1.4199(16) no
C3 C4 1.3872(17) no
C4 C5 1.4175(17) no
C5 C6 1.3771(17) no
C9 C10 1.546(2) no
C10 C11 1.5148(19) no
C11 C16 1.406(2) no
C11 C12 1.406(2) no
C12 C13 1.394(2) no
C13 C14 1.390(3) no
C14 C15 1.394(3) no
C15 C16 1.3898(19) no
C3 H3 0.9500 no
C5 H5 0.9500 no
C6 H6 0.9500 no
C7 H7 0.9500 no
C9 H9A 0.9900 no
C9 H9B 0.9900 no
C10 H10A 0.9900 no
C10 H10B 0.9900 no
C12 H12 0.9500 no
C13 H13 0.9500 no
C14 H14 0.9500 no
C15 H15 0.9500 no
C16 H16 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
N8 H8 O1 . 0.86 1.90 2.5884(15) 137 yes
O4 H4 O1 2_746 0.82 1.87 2.6902(15) 176 yes
C6 H6 O4 2_756 0.95 2.59 3.2818(18) 130 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
C9 N8 C7 C2 177.35(15) no
C7 N8 C9 C10 121.46(15) no
C6 C1 C2 C3 -0.5(2) no
C6 C1 C2 C7 -179.18(14) no
O1 C1 C6 C5 -178.71(15) no
C2 C1 C6 C5 1.3(2) no
O1 C1 C2 C7 0.8(2) no
O1 C1 C2 C3 179.54(14) no
C7 C2 C3 C4 178.19(15) no
C1 C2 C3 C4 -0.5(2) no
C3 C2 C7 N8 -177.33(15) no
C1 C2 C7 N8 1.4(2) no
C2 C3 C4 C5 0.7(2) no
C2 C3 C4 O4 -178.96(15) no
O4 C4 C5 C6 179.78(16) no
C3 C4 C5 C6 0.1(3) no
C4 C5 C6 C1 -1.1(2) no
N8 C9 C10 C11 62.54(15) no
C9 C10 C11 C12 -113.64(16) no
C9 C10 C11 C16 65.94(16) no
C10 C11 C12 C13 -179.82(14) no
C16 C11 C12 C13 0.6(2) no
C10 C11 C16 C15 179.90(13) no
C12 C11 C16 C15 -0.5(2) no
C11 C12 C13 C14 0.2(2) no
C12 C13 C14 C15 -1.0(2) no
C13 C14 C15 C16 1.1(2) no
C14 C15 C16 C11 -0.3(2) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657916
