Energetics and structure of hydroxynicotinic acids. Crystal structures of 2-, 4-, 6-hydroxynicotinic and 5-chloro-6-hydroxynicotinic acids.
Santos, Rui C.; Figueira, Rita M. B. B. M.; Piedade, M Fátima M; Diogo, Hermínio P; Minas da Piedade, Manuel E.; The journal of physical chemistry. B 113 (2009) 14291–14309; doi:10.1021/jp906908n

data_1516411
_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           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                82.55(2)
_cell_angle_beta                 78.279(17)
_cell_angle_gamma                75.166(15)
_cell_formula_units_Z            8
_cell_length_a                   6.976(2)
_cell_length_b                   11.231(5)
_cell_length_c                   16.290(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      43.39
_cell_measurement_theta_min      14.54
_cell_volume                     1203.9(8)
_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 0.983
_diffrn_measured_fraction_theta_max 0.983
_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    0.0269
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4218
_diffrn_reflns_theta_full        66.94
_diffrn_reflns_theta_max         66.94
_diffrn_reflns_theta_min         4.09
_diffrn_standards_decay_%        -2
_diffrn_standards_interval_time  90
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          .07
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         4218
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0654
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1286P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1662
_refine_ls_wR_factor_ref         0.1904
_reflns_number_gt                2694
_reflns_number_total             4218
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jp906908n_si_004.cif
_cod_data_source_block           6manello
_cod_original_cell_volume        1204.0(8)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1516411