#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/82/2228296.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228296
loop_
_publ_author_name
'Tahir, M. Nawaz'
'Shad, Hazoor Ahmad'
_publ_section_title
;
 2-Hydroxy-5-[(E)-(1H-indol-3-ylmethylidene)azaniumyl]benzoate
;
_journal_coeditor_code           DN2627
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3314
_journal_paper_doi               10.1107/S1600536810048579
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H12 N2 O3'
_chemical_formula_moiety         'C16 H12 N2 O3'
_chemical_formula_sum            'C16 H12 N2 O3'
_chemical_formula_weight         280.28
_chemical_name_systematic
;
2-Hydroxy-5-[(E)-(1H-indol-3-ylmethylidene)azaniumyl]benzoate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 104.619(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3463(6)
_cell_length_b                   15.5496(12)
_cell_length_c                   11.5310(8)
_cell_measurement_reflns_used    1169
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.25
_cell_measurement_theta_min      2.25
_cell_volume                     1274.57(17)
_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, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.20
_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
_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  0.0804
_diffrn_reflns_av_sigmaI/netI    0.0949
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9888
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         2.25
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.222
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2313
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.1362
_refine_ls_R_factor_gt           0.0568
_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)+(0.0622P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1524
_reflns_number_gt                1169
_reflns_number_total             2313
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2627.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2228296
_cod_database_fobs_code          2228296
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+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_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 1.2830(3) 0.00635(16) 0.14061(19) 0.0527(10) Uani . . 1.000
O O2 1.3616(3) 0.01396(16) 0.34045(19) 0.0529(10) Uani . . 1.000
O O3 1.1429(3) 0.07152(17) 0.44973(17) 0.0486(9) Uani . . 1.000
N N1 0.6066(4) 0.10087(18) 0.0169(2) 0.0394(10) Uani . . 1.000
N N2 0.1653(4) 0.11644(18) -0.3115(2) 0.0408(10) Uani . . 1.000
C C1 1.2446(5) 0.0237(2) 0.2380(3) 0.0375(12) Uani . . 1.000
C C2 1.0566(4) 0.0584(2) 0.2369(3) 0.0334(11) Uani . . 1.000
C C3 1.0142(5) 0.0819(2) 0.3454(3) 0.0364(11) Uani . . 1.000
C C4 0.8368(5) 0.1138(2) 0.3417(3) 0.0459(13) Uani . . 1.000
C C5 0.7012(5) 0.1219(2) 0.2364(3) 0.0424(14) Uani . . 1.000
C C6 0.7423(4) 0.0983(2) 0.1288(3) 0.0338(11) Uani . . 1.000
C C7 0.9190(4) 0.0666(2) 0.1312(3) 0.0349(11) Uani . . 1.000
C C8 0.4406(5) 0.1355(2) -0.0070(3) 0.0387(11) Uani . . 1.000
C C9 0.3080(5) 0.1370(2) -0.1184(3) 0.0344(11) Uani . . 1.000
C C10 0.1205(4) 0.1715(2) -0.1405(3) 0.0324(11) Uani . . 1.000
C C11 0.0164(5) 0.2123(2) -0.0705(3) 0.0410(11) Uani . . 1.000
C C12 -0.1644(5) 0.2377(2) -0.1229(3) 0.0451(12) Uani . . 1.000
C C13 -0.2477(5) 0.2216(2) -0.2434(3) 0.0476(14) Uani . . 1.000
C C14 -0.1494(5) 0.1805(2) -0.3140(3) 0.0411(11) Uani . . 1.000
C C15 0.0346(5) 0.1569(2) -0.2617(3) 0.0350(11) Uani . . 1.000
C C16 0.3256(5) 0.1038(2) -0.2278(3) 0.0411(12) Uani . . 1.000
H H1 0.63809 0.07659 -0.04221 0.0472 Uiso . . 1.000
H H2 0.14581 0.10162 -0.38548 0.0489 Uiso . . 1.000
H H3 1.24072 0.05315 0.43705 0.0584 Uiso . . 1.000
H H4 0.80901 0.13014 0.41293 0.0551 Uiso . . 1.000
H H5 0.58271 0.14295 0.23633 0.0512 Uiso . . 1.000
H H7 0.94585 0.05043 0.05962 0.0420 Uiso . . 1.000
H H8 0.40583 0.16216 0.05637 0.0463 Uiso . . 1.000
H H11 0.06906 0.22218 0.01060 0.0494 Uiso . . 1.000
H H12 -0.23290 0.26623 -0.07704 0.0542 Uiso . . 1.000
H H13 -0.37122 0.23872 -0.27642 0.0567 Uiso . . 1.000
H H14 -0.20470 0.16904 -0.39435 0.0495 Uiso . . 1.000
H H16 0.43238 0.07717 -0.24027 0.0491 Uiso . . 1.000
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_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 O3 H3 . . . 109.00 no
C6 N1 C8 . . . 127.8(3) no
C15 N2 C16 . . . 110.1(3) no
C8 N1 H1 . . . 116.00 no
C6 N1 H1 . . . 116.00 no
C16 N2 H2 . . . 125.00 no
C15 N2 H2 . . . 125.00 no
O2 C1 C2 . . . 117.3(3) no
O1 C1 O2 . . . 123.3(3) no
O1 C1 C2 . . . 119.4(3) no
C3 C2 C7 . . . 118.9(3) no
C1 C2 C3 . . . 120.1(3) no
C1 C2 C7 . . . 121.0(3) no
O3 C3 C4 . . . 121.1(3) no
O3 C3 C2 . . . 120.1(3) no
C2 C3 C4 . . . 118.8(3) no
C3 C4 C5 . . . 121.9(3) no
C4 C5 C6 . . . 119.4(3) no
C5 C6 C7 . . . 119.2(3) no
N1 C6 C5 . . . 122.7(3) no
N1 C6 C7 . . . 118.0(3) no
C2 C7 C6 . . . 121.7(3) no
N1 C8 C9 . . . 126.8(3) no
C8 C9 C10 . . . 125.5(3) no
C8 C9 C16 . . . 128.2(3) no
C10 C9 C16 . . . 106.3(3) no
C11 C10 C15 . . . 118.4(3) no
C9 C10 C15 . . . 106.7(3) no
C9 C10 C11 . . . 134.9(3) no
C10 C11 C12 . . . 119.1(3) no
C11 C12 C13 . . . 121.4(3) no
C12 C13 C14 . . . 120.7(3) no
C13 C14 C15 . . . 117.8(3) no
C10 C15 C14 . . . 122.5(3) no
N2 C15 C10 . . . 107.6(3) no
N2 C15 C14 . . . 129.9(3) no
N2 C16 C9 . . . 109.4(3) no
C3 C4 H4 . . . 119.00 no
C5 C4 H4 . . . 119.00 no
C4 C5 H5 . . . 120.00 no
C6 C5 H5 . . . 120.00 no
C2 C7 H7 . . . 119.00 no
C6 C7 H7 . . . 119.00 no
N1 C8 H8 . . . 117.00 no
C9 C8 H8 . . . 117.00 no
C10 C11 H11 . . . 120.00 no
C12 C11 H11 . . . 120.00 no
C11 C12 H12 . . . 119.00 no
C13 C12 H12 . . . 119.00 no
C12 C13 H13 . . . 120.00 no
C14 C13 H13 . . . 120.00 no
C13 C14 H14 . . . 121.00 no
C15 C14 H14 . . . 121.00 no
N2 C16 H16 . . . 125.00 no
C9 C16 H16 . . . 125.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . . 1.254(4) no
O2 C1 . . 1.283(4) no
O3 C3 . . 1.339(4) no
O3 H3 . . 0.8200 no
N1 C6 . . 1.418(4) no
N1 C8 . . 1.298(5) no
N2 C16 . . 1.335(4) no
N2 C15 . . 1.388(5) no
N1 H1 . . 0.8600 no
N2 H2 . . 0.8600 no
C1 C2 . . 1.480(5) no
C2 C7 . . 1.379(5) no
C2 C3 . . 1.412(5) no
C3 C4 . . 1.385(5) no
C4 C5 . . 1.368(5) no
C5 C6 . . 1.398(5) no
C6 C7 . . 1.382(4) no
C8 C9 . . 1.403(5) no
C9 C10 . . 1.440(5) no
C9 C16 . . 1.399(5) no
C10 C15 . . 1.399(5) no
C10 C11 . . 1.397(5) no
C11 C12 . . 1.371(5) no
C12 C13 . . 1.392(5) no
C13 C14 . . 1.375(5) no
C14 C15 . . 1.384(5) no
C4 H4 . . 0.9300 no
C5 H5 . . 0.9300 no
C7 H7 . . 0.9300 no
C8 H8 . . 0.9300 no
C11 H11 . . 0.9300 no
C12 H12 . . 0.9300 no
C13 H13 . . 0.9300 no
C14 H14 . . 0.9300 no
C16 H16 . . 0.9300 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
N1 H1 O1 3_755 0.86 1.90 2.735(3) 162 yes
N2 H2 O3 1_454 0.86 1.95 2.805(3) 171 yes
O3 H3 O2 . 0.82 1.70 2.448(3) 150 yes
C16 H16 O1 3_755 0.93 2.48 3.279(4) 144 yes
C16 H16 O2 3_755 0.93 2.55 3.439(4) 160 yes
C5 H5 Cg3 4_555 0.93 2.92 3.643(4) 136 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656343
