#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:01:59 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301802 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/60/2106007.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2106007
loop_
_publ_author_name
'Zhang, Qi'
'Li, Meiqi'
'Mei, Xuefeng'
_publ_section_title
;
 A new polymorph of 1-hydroxy-2-naphthoic acid obtained during failed
 co-crystallization experiments
;
_journal_coeditor_code           RY5063
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052520614026134
_journal_volume                  71
_journal_year                    2015
_chemical_formula_moiety         'C11 H8 O3'
_chemical_formula_sum            'C11 H8 O3'
_chemical_formula_weight         188.17
_chemical_name_common            HNA
_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                90.00
_cell_angle_beta                 93.901(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9798(9)
_cell_length_b                   3.8107(6)
_cell_length_c                   32.790(5)
_cell_measurement_reflns_used    1909
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.21
_cell_measurement_theta_min      2.49
_cell_volume                     870.1(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            6187
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.49
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       columnar
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.163
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         1491
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.961
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0538P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0969
_reflns_number_gt                1020
_reflns_number_total             1491
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ry5063sup1.cif
_cod_data_source_block           mo_I
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               2106007
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O3 0.25506(17) 0.8378(3) 0.99359(4) 0.0618(4) Uani d . 1 1
H H2 0.346(3) 0.937(5) 1.0124(7) 0.093 Uiso d . 1 1
O O2 0.48854(16) 0.8996(3) 0.95134(3) 0.0557(4) Uani d . 1 1
O O1 0.42771(17) 0.6877(3) 0.87621(4) 0.0566(4) Uani d . 1 1
H H1 0.493(3) 0.780(5) 0.8993(7) 0.085 Uiso d . 1 1
C C11 0.3227(2) 0.8048(4) 0.95749(5) 0.0418(4) Uani d . 1 1
C C2 0.1919(2) 0.6527(3) 0.92614(5) 0.0379(4) Uani d . 1 1
C C3 0.0036(2) 0.5550(4) 0.93476(5) 0.0441(4) Uani d . 1 1
H H3 -0.0371 0.5907 0.9609 0.053 Uiso calc R 1 1
C C4 -0.1183(2) 0.4107(4) 0.90569(5) 0.0475(4) Uani d . 1 1
H H4 -0.2414 0.3479 0.9121 0.057 Uiso calc R 1 1
C C5 -0.0614(2) 0.3540(3) 0.86576(5) 0.0421(4) Uani d . 1 1
C C6 -0.1863(3) 0.2058(4) 0.83462(6) 0.0541(5) Uani d . 1 1
H H5 -0.3104 0.1427 0.8403 0.065 Uiso calc R 1 1
C C7 -0.1271(3) 0.1547(4) 0.79662(6) 0.0632(6) Uani d . 1 1
H H6 -0.2113 0.0571 0.7765 0.076 Uiso calc R 1 1
C C10 0.1249(2) 0.4484(3) 0.85586(5) 0.0397(4) Uani d . 1 1
C C9 0.1826(3) 0.3905(4) 0.81634(5) 0.0545(5) Uani d . 1 1
H H8 0.3062 0.4504 0.8099 0.065 Uiso calc R 1 1
C C8 0.0574(3) 0.2457(5) 0.78713(5) 0.0632(5) Uani d . 1 1
H H7 0.0958 0.2083 0.7609 0.076 Uiso calc R 1 1
C C1 0.2516(2) 0.6003(3) 0.88710(5) 0.0392(4) Uani d . 1 1
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'
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
C11 O3 H2 111.4(13)
C1 O1 H1 106.4(13)
O2 C11 O3 121.08(15)
O2 C11 C2 123.41(14)
O3 C11 C2 115.51(14)
C1 C2 C3 119.26(14)
C1 C2 C11 119.84(14)
C3 C2 C11 120.90(14)
C4 C3 C2 121.05(15)
C4 C3 H3 119.5
C2 C3 H3 119.5
C3 C4 C5 120.94(15)
C3 C4 H4 119.5
C5 C4 H4 119.5
C10 C5 C4 119.83(14)
C10 C5 C6 117.98(15)
C4 C5 C6 122.19(16)
C7 C6 C5 120.68(18)
C7 C6 H5 119.7
C5 C6 H5 119.7
C6 C7 C8 121.08(17)
C6 C7 H6 119.5
C8 C7 H6 119.5
C9 C10 C5 120.07(15)
C9 C10 C1 121.61(15)
C5 C10 C1 118.32(14)
C8 C9 C10 120.07(18)
C8 C9 H8 120.0
C10 C9 H8 120.0
C9 C8 C7 120.11(18)
C9 C8 H7 119.9
C7 C8 H7 119.9
O1 C1 C2 123.15(14)
O1 C1 C10 116.24(14)
C2 C1 C10 120.61(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 C11 1.3102(19)
O3 H2 0.93(2)
O2 C11 1.2417(17)
O1 C1 1.3447(18)
O1 H1 0.92(2)
C11 C2 1.449(2)
C2 C1 1.388(2)
C2 C3 1.413(2)
C3 C4 1.351(2)
C3 H3 0.9300
C4 C5 1.410(2)
C4 H4 0.9300
C5 C10 1.408(2)
C5 C6 1.414(2)
C6 C7 1.353(3)
C6 H5 0.9300
C7 C8 1.389(3)
C7 H6 0.9300
C10 C9 1.400(2)
C10 C1 1.430(2)
C9 C8 1.368(3)
C9 H8 0.9300
C8 H7 0.9300
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
O2 C11 C2 C1 1.3(2)
O3 C11 C2 C1 -178.66(13)
O2 C11 C2 C3 -178.95(14)
O3 C11 C2 C3 1.1(2)
C1 C2 C3 C4 0.2(2)
C11 C2 C3 C4 -179.49(13)
C2 C3 C4 C5 -0.2(2)
C3 C4 C5 C10 0.0(2)
C3 C4 C5 C6 -179.54(13)
C10 C5 C6 C7 0.5(2)
C4 C5 C6 C7 -179.97(14)
C5 C6 C7 C8 0.1(2)
C4 C5 C10 C9 179.55(13)
C6 C5 C10 C9 -0.9(2)
C4 C5 C10 C1 0.1(2)
C6 C5 C10 C1 179.64(12)
C5 C10 C9 C8 0.8(2)
C1 C10 C9 C8 -179.76(14)
C10 C9 C8 C7 -0.2(2)
C6 C7 C8 C9 -0.2(3)
C3 C2 C1 O1 179.56(12)
C11 C2 C1 O1 -0.7(2)
C3 C2 C1 C10 -0.2(2)
C11 C2 C1 C10 179.58(12)
C9 C10 C1 O1 0.8(2)
C5 C10 C1 O1 -179.73(11)
C9 C10 C1 C2 -179.47(13)
C5 C10 C1 C2 0.0(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 6844
