#------------------------------------------------------------------------------
#$Date: 2023-11-24 11:23:29 +0200 (Fri, 24 Nov 2023) $
#$Revision: 287776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/76/8107676.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_8107676
loop_
_publ_author_name
'Smith, Mark G.'
_publ_section_title
;
 The crystal structure of a new polymorph of 6-hydroxy-2-naphthoic acid,
 C11H8O3
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1113
_journal_page_last               1114
_journal_paper_doi               10.1515/ncrs-2023-0345
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C11  H8  O3'
_chemical_formula_sum            'C11 H8 O3'
_chemical_formula_weight         188.17
_chemical_name_common            '6-hydroxy-2-naphthoic acid'
_chemical_name_systematic
;
6-hydroxy-2-naphthoic acid
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_cell_angle_alpha                90
_cell_angle_beta                 94.518(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6478(8)
_cell_length_b                   5.2261(5)
_cell_length_c                   18.7921(18)
_cell_measurement_reflns_used    1837
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.99
_cell_measurement_theta_min      3.08
_cell_measurement_wavelength     0.71073
_cell_volume                     846.66(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type
'Bruker D8 Venture Microfocus with Photon III CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.044
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8668
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.989
_diffrn_reflns_theta_min         2.174
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016) [1]'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.284
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     133
_refine_ls_number_reflns         2042
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0419
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0521P)²+0.1489P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1181
_reflns_Friedel_coverage         0
_reflns_number_gt                1311
_reflns_number_total             2043
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2023-0345_suppl_001.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8107676
_shelx_shelxl_version_number     2018/3
_publcif_funding_html
;
;
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_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
C1 C 0.81899(18) 0.4941(3) 0.55233(9) 0.0315(4) Uani 1 1 d . . . . .
C2 C 0.67520(18) 0.4821(3) 0.58940(8) 0.0304(4) Uani 1 1 d . . . . .
C3 C 0.55872(19) 0.6568(3) 0.57537(8) 0.0314(4) Uani 1 1 d . . . . .
H3 H 0.571947 0.790471 0.542146 0.038 Uiso 1 1 calc R U . . .
C4 C 0.41878(18) 0.6413(3) 0.60963(8) 0.0296(4) Uani 1 1 d . . . . .
C5 C 0.29684(19) 0.8197(3) 0.59664(9) 0.0345(4) Uani 1 1 d . . . . .
H5 H 0.306845 0.95312 0.562967 0.041 Uiso 1 1 calc R U . . .
C6 C 0.1651(2) 0.8030(3) 0.63177(9) 0.0347(4) Uani 1 1 d . . . . .
H6 H 0.084072 0.924134 0.622707 0.042 Uiso 1 1 calc R U . . .
C7 C 0.15007(19) 0.6054(3) 0.68145(9) 0.0325(4) Uani 1 1 d . . . . .
C8 C 0.26281(19) 0.4266(3) 0.69461(9) 0.0327(4) Uani 1 1 d . . . . .
H8 H 0.248988 0.292491 0.727655 0.039 Uiso 1 1 calc R U . . .
C9 C 0.40051(18) 0.4403(3) 0.65907(8) 0.0294(4) Uani 1 1 d . . . . .
C10 C 0.52289(19) 0.2637(3) 0.67250(9) 0.0341(4) Uani 1 1 d . . . . .
H10 H 0.511929 0.128701 0.705574 0.041 Uiso 1 1 calc R U . . .
C11 C 0.65640(19) 0.2832(3) 0.63894(9) 0.0348(4) Uani 1 1 d . . . . .
H11 H 0.73732 0.162391 0.648883 0.042 Uiso 1 1 calc R U . . .
O1 O 0.83436(15) 0.6859(2) 0.51021(7) 0.0412(3) Uani 1 1 d . . . . .
H1 H 0.933(2) 0.680(4) 0.4850(10) 0.051 Uiso 1 1 d . U . . .
O2 O 0.01563(14) 0.6079(3) 0.71664(7) 0.0401(3) Uani 1 1 d . . . . .
H2 H 0.010(2) 0.470(4) 0.7381(11) 0.051 Uiso 1 1 d . U . . .
O3 O 0.91920(13) 0.3217(2) 0.56176(6) 0.0383(3) Uani 1 1 d . . . . .
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
C1 O1 H1 113.5(11) . .
C7 O2 H2 107.8(15) . .
C10 C9 C8 122.04(15) . .
C10 C9 C4 118.69(15) . .
C8 C9 C4 119.25(15) . .
O3 C1 O1 122.80(15) . .
O3 C1 C2 120.17(15) . .
O1 C1 C2 117.03(15) . .
C8 C7 O2 122.53(16) . .
C8 C7 C6 121.57(15) . .
O2 C7 C6 115.89(15) . .
C7 C8 C9 119.90(16) . .
C7 C8 H8 120.1 . .
C9 C8 H8 120.1 . .
C5 C4 C3 122.39(15) . .
C5 C4 C9 118.74(15) . .
C3 C4 C9 118.87(15) . .
C3 C2 C11 119.74(15) . .
C3 C2 C1 121.06(15) . .
C11 C2 C1 119.19(15) . .
C2 C3 C4 121.06(15) . .
C2 C3 H3 119.5 . .
C4 C3 H3 119.5 . .
C6 C5 C4 120.93(16) . .
C6 C5 H5 119.5 . .
C4 C5 H5 119.5 . .
C10 C11 C2 120.36(16) . .
C10 C11 H11 119.8 . .
C2 C11 H11 119.8 . .
C5 C6 C7 119.58(16) . .
C5 C6 H6 120.2 . .
C7 C6 H6 120.2 . .
C11 C10 C9 121.28(15) . .
C11 C10 H10 119.4 . .
C9 C10 H10 119.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O3 C1 1.2529(19) .
O1 C1 1.290(2) .
O1 H1 1.01(2) .
O2 C7 1.382(2) .
O2 H2 0.83(2) .
C9 C10 1.412(2) .
C9 C8 1.412(2) .
C9 C4 1.419(2) .
C1 C2 1.474(2) .
C7 C8 1.359(2) .
C7 C6 1.405(2) .
C8 H8 0.95 .
C4 C5 1.415(2) .
C4 C3 1.417(2) .
C2 C3 1.369(2) .
C2 C11 1.413(2) .
C3 H3 0.95 .
C5 C6 1.364(2) .
C5 H5 0.95 .
C11 C10 1.362(2) .
C11 H11 0.95 .
C6 H6 0.95 .
C10 H10 0.95 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O3 1.01(2) 1.61(2) 2.6128(17) 174.7(17) 3_766 yes
O2 H2 O2 0.83(2) 2.09(2) 2.9200(11) 175(2) 2_546 yes
O1 H1 O3 1.01(2) 1.61(2) 2.6128(17) 174.7(17) 3_766 yes
O2 H2 O2 0.83(2) 2.09(2) 2.9200(11) 175(2) 2_546 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O2 C7 C8 C9 -177.36(15) . . . .
C6 C7 C8 C9 1.4(2) . . . .
C10 C9 C8 C7 178.05(15) . . . .
C4 C9 C8 C7 -0.3(2) . . . .
C10 C9 C4 C5 -179.41(15) . . . .
C8 C9 C4 C5 -1.0(2) . . . .
C10 C9 C4 C3 0.2(2) . . . .
C8 C9 C4 C3 178.65(15) . . . .
O3 C1 C2 C3 -174.55(15) . . . .
O1 C1 C2 C3 4.8(2) . . . .
O3 C1 C2 C11 3.9(2) . . . .
O1 C1 C2 C11 -176.72(15) . . . .
C11 C2 C3 C4 -0.2(2) . . . .
C1 C2 C3 C4 178.31(15) . . . .
C5 C4 C3 C2 179.55(15) . . . .
C9 C4 C3 C2 -0.1(2) . . . .
C3 C4 C5 C6 -178.41(16) . . . .
C9 C4 C5 C6 1.2(2) . . . .
C3 C2 C11 C10 0.3(2) . . . .
C1 C2 C11 C10 -178.23(16) . . . .
C4 C5 C6 C7 -0.1(2) . . . .
C8 C7 C6 C5 -1.2(2) . . . .
O2 C7 C6 C5 177.65(15) . . . .
C2 C11 C10 C9 -0.1(3) . . . .
C8 C9 C10 C11 -178.49(16) . . . .
C4 C9 C10 C11 -0.1(2) . . . .
