#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/04/2230464.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_2230464
loop_
_publ_author_name
'Bahron, Hadariah'
'Fadzel, Fatimatuzzahraa Mohd'
'Kassim, Karimah'
'Hemamalini, Madhukar'
'Fun, Hoong-Kun'
_publ_section_title
;
 2-[(E)-(2,4-Dihydroxybenzylidene)azaniumyl]-3-phenylpropanoate
;
_journal_coeditor_code           RZ2592
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1331
_journal_page_last               o1332
_journal_paper_doi               10.1107/S1600536811016655
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H15 N O4'
_chemical_formula_moiety         'C16 H15 N O4'
_chemical_formula_sum            'C16 H15 N O4'
_chemical_formula_weight         285.29
_chemical_name_systematic
;
2-[(E)-(2,4-Dihydroxybenzylidene)azaniumyl]-3-phenylpropanoate
;
_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                90.00
_cell_angle_beta                 92.0650(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.39430(10)
_cell_length_b                   6.89460(10)
_cell_length_c                   20.7251(3)
_cell_measurement_reflns_used    9091
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      35.26
_cell_measurement_theta_min      2.98
_cell_volume                     1341.49(3)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(10)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and 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  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            22479
_diffrn_reflns_theta_full        35.32
_diffrn_reflns_theta_max         35.32
_diffrn_reflns_theta_min         1.97
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9824
_exptl_absorpt_correction_T_min  0.9659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.239
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         6007
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0674P)²+0.2835P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1248
_reflns_number_gt                4783
_reflns_number_total             6007
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2592.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2230464
_cod_database_fobs_code          2230464
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.60361(6) 0.80079(9) 0.04375(3) 0.01400(12) Uani d . 1 1 . .
O O2 0.97519(6) 0.33854(10) 0.05402(3) 0.01685(13) Uani d . 1 1 . .
O O3 0.03702(7) 0.98745(10) 0.07713(4) 0.01988(14) Uani d . 1 1 . .
O O4 0.26610(7) 1.04016(9) 0.05323(3) 0.01783(13) Uani d . 1 1 . .
N N1 0.34885(7) 0.69321(10) 0.08580(3) 0.01219(12) Uani d . 1 1 . .
C C1 0.33058(10) 0.53563(14) 0.25232(4) 0.01942(16) Uani d . 1 1 . .
H H1A 0.3954 0.6401 0.2590 0.023 Uiso calc R 1 1 . .
C C2 0.35367(11) 0.36077(15) 0.28493(5) 0.02434(19) Uani d . 1 1 . .
H H2A 0.4337 0.3473 0.3139 0.029 Uiso calc R 1 1 . .
C C3 0.26067(12) 0.20648(14) 0.27537(5) 0.02416(19) Uani d . 1 1 . .
H H3A 0.2770 0.0875 0.2975 0.029 Uiso calc R 1 1 . .
C C4 0.14316(11) 0.22715(13) 0.23307(5) 0.02018(17) Uani d . 1 1 . .
H H4A 0.0792 0.1219 0.2262 0.024 Uiso calc R 1 1 . .
C C5 0.11937(9) 0.40174(13) 0.20089(4) 0.01695(15) Uani d . 1 1 . .
H H5A 0.0386 0.4150 0.1723 0.020 Uiso calc R 1 1 . .
C C6 0.21269(9) 0.55797(12) 0.20999(4) 0.01422(14) Uani d . 1 1 . .
C C7 0.18457(9) 0.74664(12) 0.17511(4) 0.01563(15) Uani d . 1 1 . .
H H7A 0.2505 0.8462 0.1933 0.019 Uiso calc R 1 1 . .
H H7B 0.0863 0.7891 0.1836 0.019 Uiso calc R 1 1 . .
C C8 0.20180(8) 0.73766(12) 0.10126(4) 0.01250(13) Uani d . 1 1 . .
H H8A 0.1359 0.6381 0.0817 0.015 Uiso calc R 1 1 . .
C C9 0.40809(8) 0.52254(11) 0.09102(4) 0.01214(13) Uani d . 1 1 . .
H H9A 0.3492 0.4173 0.1029 0.015 Uiso calc R 1 1 . .
C C10 0.55370(8) 0.48144(11) 0.08037(4) 0.01121(13) Uani d . 1 1 . .
C C11 0.65246(8) 0.61982(11) 0.05775(4) 0.01132(13) Uani d . 1 1 . .
C C12 0.79342(8) 0.56952(12) 0.04987(4) 0.01286(14) Uani d . 1 1 . .
H H12A 0.8591 0.6634 0.0354 0.015 Uiso calc R 1 1 . .
C C13 0.83916(8) 0.37933(12) 0.06334(4) 0.01261(14) Uani d . 1 1 . .
C C14 0.74286(8) 0.23932(12) 0.08580(4) 0.01396(14) Uani d . 1 1 . .
H H14A 0.7742 0.1113 0.0955 0.017 Uiso calc R 1 1 . .
C C15 0.60318(8) 0.29109(12) 0.09343(4) 0.01367(14) Uani d . 1 1 . .
H H15A 0.5381 0.1965 0.1079 0.016 Uiso calc R 1 1 . .
C C16 0.16518(8) 0.93989(12) 0.07349(4) 0.01381(14) Uani d . 1 1 . .
H H1O1 0.6599(16) 0.855(2) 0.0171(7) 0.030(4) Uiso d . 1 1 . .
H H1N1 0.3969(16) 0.791(2) 0.0723(7) 0.033(4) Uiso d . 1 1 . .
H H1O2 0.999(2) 0.196(3) 0.0635(8) 0.052(5) Uiso d . 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 O1 H1O1 . . 108.9(10) ?
C13 O2 H1O2 . . 112.1(10) ?
C9 N1 C8 . . 125.08(7) ?
C9 N1 H1N1 . . 120.3(10) ?
C8 N1 H1N1 . . 114.6(10) ?
C2 C1 C6 . . 120.37(9) ?
C2 C1 H1A . . 119.8 ?
C6 C1 H1A . . 119.8 ?
C3 C2 C1 . . 120.51(9) ?
C3 C2 H2A . . 119.7 ?
C1 C2 H2A . . 119.7 ?
C2 C3 C4 . . 119.53(9) ?
C2 C3 H3A . . 120.2 ?
C4 C3 H3A . . 120.2 ?
C5 C4 C3 . . 120.06(9) ?
C5 C4 H4A . . 120.0 ?
C3 C4 H4A . . 120.0 ?
C4 C5 C6 . . 120.90(8) ?
C4 C5 H5A . . 119.6 ?
C6 C5 H5A . . 119.6 ?
C1 C6 C5 . . 118.64(8) ?
C1 C6 C7 . . 121.20(8) ?
C5 C6 C7 . . 120.17(8) ?
C6 C7 C8 . . 114.68(7) ?
C6 C7 H7A . . 108.6 ?
C8 C7 H7A . . 108.6 ?
C6 C7 H7B . . 108.6 ?
C8 C7 H7B . . 108.6 ?
H7A C7 H7B . . 107.6 ?
N1 C8 C16 . . 107.91(6) ?
N1 C8 C7 . . 111.03(6) ?
C16 C8 C7 . . 107.65(6) ?
N1 C8 H8A . . 110.1 ?
C16 C8 H8A . . 110.1 ?
C7 C8 H8A . . 110.1 ?
N1 C9 C10 . . 125.23(7) ?
N1 C9 H9A . . 117.4 ?
C10 C9 H9A . . 117.4 ?
C15 C10 C9 . . 117.79(7) ?
C15 C10 C11 . . 118.13(7) ?
C9 C10 C11 . . 124.07(7) ?
O1 C11 C12 . . 121.51(7) ?
O1 C11 C10 . . 117.88(7) ?
C12 C11 C10 . . 120.60(7) ?
C11 C12 C13 . . 119.84(7) ?
C11 C12 H12A . . 120.1 ?
C13 C12 H12A . . 120.1 ?
O2 C13 C12 . . 117.22(7) ?
O2 C13 C14 . . 122.24(7) ?
C12 C13 C14 . . 120.54(7) ?
C15 C14 C13 . . 119.06(7) ?
C15 C14 H14A . . 120.5 ?
C13 C14 H14A . . 120.5 ?
C14 C15 C10 . . 121.81(7) ?
C14 C15 H15A . . 119.1 ?
C10 C15 H15A . . 119.1 ?
O3 C16 O4 . . 127.87(8) ?
O3 C16 C8 . . 114.59(7) ?
O4 C16 C8 . . 117.43(7) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C11 . 1.3572(9) ?
O1 H1O1 . 0.863(15) ?
O2 C13 . 1.3293(10) ?
O2 H1O2 . 1.025(19) ?
O3 C16 . 1.2527(10) ?
O4 C16 . 1.2577(10) ?
N1 C9 . 1.3045(10) ?
N1 C8 . 1.4617(10) ?
N1 H1N1 . 0.864(16) ?
C1 C2 . 1.3952(13) ?
C1 C6 . 1.3965(12) ?
C1 H1A . 0.9500 ?
C2 C3 . 1.3863(16) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.3921(15) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.3903(13) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.3973(12) ?
C5 H5A . 0.9500 ?
C6 C7 . 1.5068(12) ?
C7 C8 . 1.5461(12) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 C16 . 1.5425(11) ?
C8 H8A . 1.0000 ?
C9 C10 . 1.4220(11) ?
C9 H9A . 0.9500 ?
C10 C15 . 1.4152(11) ?
C10 C11 . 1.4220(11) ?
C11 C12 . 1.3842(11) ?
C12 C13 . 1.4048(11) ?
C12 H12A . 0.9500 ?
C13 C14 . 1.4133(11) ?
C14 C15 . 1.3745(11) ?
C14 H14A . 0.9500 ?
C15 H15A . 0.9500 ?
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 H1O1 O4 3_675 0.863(15) 1.790(14) 2.6302(9) 163.9(15) yes
N1 H1N1 O1 . 0.864(14) 2.051(15) 2.6810(9) 129.1(12) yes
O2 H1O2 O3 1_645 1.03(2) 1.51(2) 2.5310(10) 179(2) yes
C5 H5A O2 1_455 0.95 2.56 3.3155(10) 137 yes
C12 H12A O2 3_765 0.95 2.46 3.1781(10) 132 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 0.53(15) ?
C1 C2 C3 C4 . . . . -0.27(15) ?
C2 C3 C4 C5 . . . . -0.22(15) ?
C3 C4 C5 C6 . . . . 0.45(14) ?
C2 C1 C6 C5 . . . . -0.29(13) ?
C2 C1 C6 C7 . . . . 179.02(8) ?
C4 C5 C6 C1 . . . . -0.19(13) ?
C4 C5 C6 C7 . . . . -179.51(8) ?
C1 C6 C7 C8 . . . . 112.09(9) ?
C5 C6 C7 C8 . . . . -68.61(10) ?
C9 N1 C8 C16 . . . . -166.85(7) ?
C9 N1 C8 C7 . . . . 75.39(10) ?
C6 C7 C8 N1 . . . . -63.66(9) ?
C6 C7 C8 C16 . . . . 178.43(7) ?
C8 N1 C9 C10 . . . . -175.36(7) ?
N1 C9 C10 C15 . . . . 174.78(8) ?
N1 C9 C10 C11 . . . . -4.90(13) ?
C15 C10 C11 O1 . . . . 178.38(7) ?
C9 C10 C11 O1 . . . . -1.95(12) ?
C15 C10 C11 C12 . . . . -1.04(11) ?
C9 C10 C11 C12 . . . . 178.63(8) ?
O1 C11 C12 C13 . . . . -178.40(7) ?
C10 C11 C12 C13 . . . . 1.00(12) ?
C11 C12 C13 O2 . . . . 179.06(7) ?
C11 C12 C13 C14 . . . . -0.93(12) ?
O2 C13 C14 C15 . . . . -179.07(8) ?
C12 C13 C14 C15 . . . . 0.92(12) ?
C13 C14 C15 C10 . . . . -0.99(13) ?
C9 C10 C15 C14 . . . . -178.64(8) ?
C11 C10 C15 C14 . . . . 1.05(12) ?
N1 C8 C16 O3 . . . . 172.58(7) ?
C7 C8 C16 O3 . . . . -67.51(9) ?
N1 C8 C16 O4 . . . . -10.87(10) ?
C7 C8 C16 O4 . . . . 109.04(8) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10483563
