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#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/64/1516414.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_1516414
loop_
_publ_author_name
'Santos, Rui C.'
'Figueira, Rita M. B. B. M.'
'Piedade, M Fátima M'
'Diogo, Hermínio P'
'Minas da Piedade, Manuel E.'
_publ_section_title
;
 Energetics and structure of hydroxynicotinic acids. Crystal structures of
 2-, 4-, 6-hydroxynicotinic and 5-chloro-6-hydroxynicotinic acids.
;
_journal_issue                   43
_journal_name_full               'The journal of physical chemistry. B'
_journal_page_first              14291
_journal_page_last               14309
_journal_paper_doi               10.1021/jp906908n
_journal_volume                  113
_journal_year                    2009
_chemical_formula_sum            'C6 H5 N O3'
_chemical_formula_weight         139.11
_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                 94.254(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.804(3)
_cell_length_b                   14.582(7)
_cell_length_c                   10.673(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      46.16
_cell_measurement_theta_min      14.84
_cell_volume                     590.4(6)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.949
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0154
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            999
_diffrn_reflns_theta_full        66.95
_diffrn_reflns_theta_max         66.95
_diffrn_reflns_theta_min         5.14
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  80
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.103
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.015(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         999
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0364
_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)+(0.0698P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0984
_reflns_number_gt                812
_reflns_number_total             999
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jp906908n_si_003.cif
_cod_data_source_block           4manelno
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1516414
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
O3 O 0.7409(5) 0.53618(8) 0.15231(12) 0.0662(5) Uani 1 1 d
O2 O 0.9968(4) 0.49459(8) 0.33547(12) 0.0616(5) Uani 1 1 d
O1 O 1.0494(4) 0.32670(7) 0.39080(10) 0.0463(4) Uani 1 1 d
N1 N 0.4706(4) 0.26656(9) 0.06721(12) 0.0397(4) Uani 1 1 d
C1 C 0.5504(4) 0.35452(10) 0.09337(13) 0.0377(4) Uani 1 1 d
C2 C 0.7455(4) 0.37753(9) 0.20154(13) 0.0343(4) Uani 1 1 d
C4 C 0.7727(5) 0.21574(10) 0.25468(14) 0.0409(4) Uani 1 1 d
C3 C 0.8666(4) 0.30730(10) 0.28886(13) 0.0343(4) Uani 1 1 d
C5 C 0.5786(5) 0.19841(10) 0.14677(15) 0.0416(4) Uani 1 1 d
C6 C 0.8261(5) 0.47611(10) 0.22630(14) 0.0446(4) Uani 1 1 d
H1 H 0.469(5) 0.3974(13) 0.0306(16) 0.047(5) Uiso 1 1 d
H4 H 0.846(6) 0.1679(15) 0.3112(18) 0.052(5) Uiso 1 1 d
H5 H 0.510(6) 0.1401(15) 0.1182(18) 0.054(5) Uiso 1 1 d
H1N H 0.331(7) 0.2493(16) -0.006(2) 0.080(7) Uiso 1 1 d
H2 H 1.036(6) 0.4370(18) 0.374(2) 0.075(7) Uiso 1 1 d
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O3 0.1072(13) 0.0261(6) 0.0605(7) 0.0091(5) -0.0256(7) -0.0038(7)
O2 0.0976(12) 0.0300(6) 0.0524(7) -0.0013(5) -0.0263(7) -0.0067(6)
O1 0.0647(8) 0.0344(6) 0.0374(6) 0.0036(4) -0.0135(5) 0.0010(5)
N1 0.0519(8) 0.0316(7) 0.0347(6) -0.0049(5) -0.0036(6) -0.0017(6)
C1 0.0519(10) 0.0277(7) 0.0329(7) 0.0016(6) -0.0017(7) 0.0027(6)
C2 0.0460(9) 0.0240(7) 0.0324(7) 0.0005(5) -0.0005(6) -0.0001(6)
C4 0.0571(10) 0.0231(7) 0.0419(8) 0.0046(6) -0.0001(7) 0.0029(6)
C3 0.0434(9) 0.0296(7) 0.0297(7) 0.0015(5) 0.0002(6) 0.0030(6)
C5 0.0551(10) 0.0254(7) 0.0439(8) -0.0030(6) 0.0020(7) -0.0008(7)
C6 0.0646(11) 0.0254(7) 0.0419(8) 0.0012(6) -0.0083(7) -0.0017(7)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C6 O2 H2 105.0(14)
C1 N1 C5 121.23(14)
C1 N1 H1N 121.9(14)
C5 N1 H1N 116.8(14)
N1 C1 C2 120.68(14)
N1 C1 H1 115.2(11)
C2 C1 H1 124.1(11)
C1 C2 C3 120.03(14)
C1 C2 C6 118.59(13)
C3 C2 C6 121.38(14)
C5 C4 C3 120.48(14)
C5 C4 H4 121.4(12)
C3 C4 H4 118.1(12)
O1 C3 C4 122.42(13)
O1 C3 C2 121.47(14)
C4 C3 C2 116.11(14)
C4 C5 N1 121.46(15)
C4 C5 H5 125.0(12)
N1 C5 H5 113.6(12)
O3 C6 O2 121.35(15)
O3 C6 C2 122.84(15)
O2 C6 C2 115.81(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 C6 1.208(2)
O2 C6 1.319(2)
O2 H2 0.94(3)
O1 C3 1.2787(19)
N1 C1 1.343(2)
N1 C5 1.351(2)
N1 H1N 0.95(2)
C1 C2 1.367(2)
C1 H1 0.951(19)
C2 C3 1.437(2)
C2 C6 1.489(2)
C4 C5 1.345(2)
C4 C3 1.423(2)
C4 H4 0.95(2)
C5 H5 0.93(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
C5 N1 C1 C2 0.3(2)
N1 C1 C2 C3 -0.2(2)
N1 C1 C2 C6 -179.86(15)
C5 C4 C3 O1 179.69(16)
C5 C4 C3 C2 -0.6(2)
C1 C2 C3 O1 -179.97(15)
C6 C2 C3 O1 -0.3(2)
C1 C2 C3 C4 0.4(2)
C6 C2 C3 C4 180.00(15)
C3 C4 C5 N1 0.8(3)
C1 N1 C5 C4 -0.6(3)
C1 C2 C6 O3 -3.6(3)
C3 C2 C6 O3 176.76(18)
C1 C2 C6 O2 176.07(16)
C3 C2 C6 O2 -3.6(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 69113
