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#$Date: 2023-03-05 05:31:43 +0200 (Sun, 05 Mar 2023) $
#$Revision: 281629 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/85/1568592.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_1568592
loop_
_publ_author_name
'Baptista, Diogo S.'
'Piedade, M. Fátima M.'
'Esteves, Catarina V.'
_publ_section_title
;
 Solubility and Crystallization Studies of Picolinic Acid
;
_journal_issue                   3
_journal_name_full               Crystals
_journal_page_first              392
_journal_paper_doi               10.3390/cryst13030392
_journal_volume                  13
_journal_year                    2023
_chemical_formula_sum            'C6 H5 N O2'
_chemical_formula_weight         123.11
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 107.653(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.2110(17)
_cell_length_b                   3.7625(3)
_cell_length_c                   13.9555(11)
_cell_measurement_reflns_used    9968
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      36.32
_cell_measurement_theta_min      2.88
_cell_volume                     1061.29(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    Mercury
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18364
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.905
_diffrn_reflns_theta_min         2.015
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.7105
_exptl_absorpt_correction_type   psi-scans
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_description       Parallelepiped
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.695
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     107
_refine_ls_number_reflns         2478
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0632
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0755P)²+0.8518P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1481
_refine_ls_wR_factor_ref         0.1565
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1932
_reflns_number_total             2478
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            20210526_ds_150k_0m_a.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1568592
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.965
_shelx_estimated_absorpt_t_max   0.977
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.52172(5) 0.5977(3) 0.09054(7) 0.0226(2) Uani 1 1 d . . . . .
O1 O 0.62409(5) 0.4671(3) 0.08524(7) 0.0242(2) Uani 1 1 d . . . . .
N1 N 0.57019(5) 0.8517(3) 0.28053(7) 0.01430(19) Uani 1 1 d . . . . .
C3 C 0.68042(6) 0.7685(3) 0.27568(8) 0.0150(2) Uani 1 1 d . . . . .
C2 C 0.61263(5) 0.7412(3) 0.23152(8) 0.0134(2) Uani 1 1 d . . . . .
C1 C 0.58530(6) 0.5878(3) 0.12661(8) 0.0159(2) Uani 1 1 d . . . . .
C6 C 0.59360(6) 0.9899(3) 0.37328(9) 0.0175(2) Uani 1 1 d . . . . .
C4 C 0.70509(6) 0.9097(3) 0.37204(9) 0.0174(2) Uani 1 1 d . . . . .
C5 C 0.66090(6) 1.0227(3) 0.42156(9) 0.0184(2) Uani 1 1 d . . . . .
H5 H 0.6746(10) 1.120(6) 0.4879(14) 0.027(5) Uiso 1 1 d . . . . .
H3 H 0.7076(10) 0.702(5) 0.2380(14) 0.025(5) Uiso 1 1 d . . . . .
H4 H 0.7517(11) 0.927(6) 0.4023(15) 0.028(5) Uiso 1 1 d . . . . .
H6 H 0.5630(11) 1.059(6) 0.4034(17) 0.037(6) Uiso 1 1 d . . . . .
H2 H 0.514(2) 0.508(12) 0.033(3) 0.033(12) Uiso 0.54(3) 1 d . . P . .
H1 H 0.5284(18) 0.823(10) 0.256(3) 0.015(10) Uiso 0.46(3) 1 d . . P . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C2 119.93(10) . . ?
C2 C3 C4 119.56(11) . . ?
N1 C2 C3 120.86(10) . . ?
N1 C2 C1 119.20(10) . . ?
C3 C2 C1 119.94(10) . . ?
O1 C1 O2 126.76(11) . . ?
O1 C1 C2 118.75(10) . . ?
O2 C1 C2 114.49(10) . . ?
N1 C6 C5 121.89(11) . . ?
C5 C4 C3 118.99(11) . . ?
C6 C5 C4 118.77(10) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C1 1.2891(15) . ?
O1 C1 1.2265(15) . ?
N1 C6 1.3425(15) . ?
N1 C2 1.3507(15) . ?
C3 C2 1.3857(16) . ?
C3 C4 1.3920(16) . ?
C2 C1 1.5159(16) . ?
C6 C5 1.3869(17) . ?
C4 C5 1.3893(18) . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 C3 -0.04(17) . . . . ?
C6 N1 C2 C1 -179.66(11) . . . . ?
C4 C3 C2 N1 0.38(17) . . . . ?
C4 C3 C2 C1 180.00(11) . . . . ?
N1 C2 C1 O1 -175.35(11) . . . . ?
C3 C2 C1 O1 5.02(17) . . . . ?
N1 C2 C1 O2 4.13(16) . . . . ?
C3 C2 C1 O2 -175.50(11) . . . . ?
C2 N1 C6 C5 -0.22(18) . . . . ?
C2 C3 C4 C5 -0.45(18) . . . . ?
N1 C6 C5 C4 0.14(19) . . . . ?
C3 C4 C5 C6 0.20(18) . . . . ?
