#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/58/2205820.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_2205820
loop_
_publ_author_name
'Jin, Long-Fei'
'Xiao, Feng-Ping'
_publ_section_title
;
 Methyl 1-hydroxy-2-naphthoate
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1520
_journal_page_last               o1522
_journal_paper_doi               10.1107/S1600536805012626
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C12 H10 O3'
_chemical_formula_moiety         'C12 H10 O3'
_chemical_formula_sum            'C12 H10 O3'
_chemical_formula_weight         202.20
_chemical_name_systematic
;
Methyl 1-hydroxy-2-naphthoate
;
_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                98.410(2)
_cell_angle_beta                 108.229(2)
_cell_angle_gamma                102.689(2)
_cell_formula_units_Z            4
_cell_length_a                   8.7325(11)
_cell_length_b                   9.0677(12)
_cell_length_c                   13.6287(17)
_cell_measurement_reflns_used    1216
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      24.4
_cell_measurement_theta_min      2.4
_cell_volume                     972.7(2)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics    'SHELXTL (Bruker, 2001)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.019
_diffrn_reflns_av_sigmaI/netI    0.043
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5729
_diffrn_reflns_theta_full        27.0
_diffrn_reflns_theta_max         27.0
_diffrn_reflns_theta_min         1.6
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.20
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4115
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.106
_refine_ls_R_factor_gt           0.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0941P)²+0.2807P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.179
_refine_ls_wR_factor_ref         0.216
_reflns_number_gt                2602
_reflns_number_total             4115
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk6222.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2205820
_cod_database_fobs_code          2205820
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
C1 0.6693(3) 0.4240(3) 0.3988(2) 0.0533(7) Uani d . 1 C
C2 0.7799(3) 0.4180(3) 0.4952(2) 0.0527(7) Uani d . 1 C
C3 0.8241(4) 0.5424(4) 0.5846(2) 0.0621(8) Uani d . 1 C
H3 0.8985 0.5397 0.6498 0.075 Uiso calc R 1 H
C4 0.7601(4) 0.6638(4) 0.5764(2) 0.0658(8) Uani d . 1 C
H4A 0.7903 0.7434 0.6362 0.079 Uiso calc R 1 H
C5 0.6472(4) 0.6729(3) 0.4780(2) 0.0579(7) Uani d . 1 C
C6 0.5791(4) 0.7991(4) 0.4655(3) 0.0713(9) Uani d . 1 C
H6 0.6087 0.8809 0.5238 0.086 Uiso calc R 1 H
C7 0.4713(4) 0.8040(4) 0.3701(3) 0.0766(10) Uani d . 1 C
H7 0.4279 0.8885 0.3637 0.092 Uiso calc R 1 H
C8 0.4258(4) 0.6815(4) 0.2816(3) 0.0700(9) Uani d . 1 C
H8 0.3516 0.6851 0.2165 0.084 Uiso calc R 1 H
C9 0.4880(4) 0.5590(4) 0.2894(2) 0.0612(8) Uani d . 1 C
H9 0.4562 0.4786 0.2298 0.073 Uiso calc R 1 H
C10 0.6012(3) 0.5508(3) 0.3873(2) 0.0519(7) Uani d . 1 C
C11 0.8444(4) 0.2824(4) 0.5027(2) 0.0605(8) Uani d . 1 C
C12 1.0149(5) 0.1567(4) 0.6133(3) 0.0802(10) Uani d . 1 C
H12A 0.9237 0.0632 0.5906 0.120 Uiso calc R 1 H
H12B 1.0805 0.1702 0.6868 0.120 Uiso calc R 1 H
H12C 1.0845 0.1496 0.5715 0.120 Uiso calc R 1 H
C13 0.0459(3) 0.7925(3) -0.0588(2) 0.0519(7) Uani d . 1 C
C14 0.0306(3) 0.7756(3) 0.0374(2) 0.0497(6) Uani d . 1 C
C15 0.1403(3) 0.8888(3) 0.1310(2) 0.0545(7) Uani d . 1 C
H15 0.1300 0.8791 0.1958 0.065 Uiso calc R 1 H
C16 0.2594(4) 1.0105(3) 0.1284(2) 0.0558(7) Uani d . 1 C
H16 0.3295 1.0826 0.1910 0.067 Uiso calc R 1 H
C17 0.2782(3) 1.0289(3) 0.0308(2) 0.0499(7) Uani d . 1 C
C18 0.4012(4) 1.1525(3) 0.0250(2) 0.0613(8) Uani d . 1 C
H18 0.4718 1.2266 0.0866 0.074 Uiso calc R 1 H
C19 0.4187(4) 1.1658(4) -0.0692(3) 0.0674(8) Uani d . 1 C
H19 0.5011 1.2486 -0.0713 0.081 Uiso calc R 1 H
C20 0.3137(4) 1.0558(4) -0.1632(2) 0.0662(8) Uani d . 1 C
H20 0.3270 1.0653 -0.2273 0.079 Uiso calc R 1 H
C21 0.1929(4) 0.9358(4) -0.1605(2) 0.0613(8) Uani d . 1 C
H21 0.1230 0.8639 -0.2233 0.074 Uiso calc R 1 H
C22 0.1709(3) 0.9176(3) -0.0643(2) 0.0499(7) Uani d . 1 C
C23 -0.0972(4) 0.6446(3) 0.0394(2) 0.0579(7) Uani d . 1 C
C24 -0.2277(4) 0.5154(4) 0.1440(3) 0.0798(10) Uani d . 1 C
H24A -0.3361 0.5284 0.1087 0.120 Uiso calc R 1 H
H24B -0.2113 0.5188 0.2174 0.120 Uiso calc R 1 H
H24C -0.2215 0.4170 0.1109 0.120 Uiso calc R 1 H
H1 0.649(4) 0.239(4) 0.332(3) 0.070(11) Uiso d . 1 H
H4 -0.118(4) 0.611(4) -0.133(3) 0.080(11) Uiso d . 1 H
O1 0.6205(3) 0.3106(3) 0.30983(16) 0.0746(7) Uani d . 1 O
O2 0.8082(3) 0.1719(2) 0.42887(17) 0.0792(7) Uani d . 1 O
O3 0.9481(3) 0.2890(3) 0.59974(15) 0.0706(6) Uani d . 1 O
O4 -0.0550(3) 0.6922(3) -0.15189(15) 0.0684(6) Uani d . 1 O
O5 -0.1979(3) 0.5465(2) -0.03919(17) 0.0748(7) Uani d . 1 O
O6 -0.0991(3) 0.6385(2) 0.13637(16) 0.0683(6) Uani d . 1 O
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
_geom_angle_publ_flag
O1 C1 C2 122.6(3) yes
O1 C1 C10 115.8(2) ?
C2 C1 C10 121.6(2) ?
C1 C2 C3 118.7(3) ?
C1 C2 C11 119.2(2) ?
C3 C2 C11 122.1(3) ?
C4 C3 C2 121.1(3) ?
C4 C3 H3 119.5 ?
C2 C3 H3 119.5 ?
C3 C4 C5 121.2(3) ?
C3 C4 H4A 119.4 ?
C5 C4 H4A 119.4 ?
C6 C5 C10 117.8(3) ?
C6 C5 C4 123.1(3) ?
C10 C5 C4 119.1(3) ?
C7 C6 C5 121.6(3) ?
C7 C6 H6 119.2 ?
C5 C6 H6 119.2 ?
C6 C7 C8 119.8(3) ?
C6 C7 H7 120.1 ?
C8 C7 H7 120.1 ?
C9 C8 C7 120.8(3) ?
C9 C8 H8 119.6 ?
C7 C8 H8 119.6 ?
C8 C9 C10 120.7(3) ?
C8 C9 H9 119.7 ?
C10 C9 H9 119.7 ?
C1 C10 C9 122.4(3) ?
C1 C10 C5 118.4(3) ?
C9 C10 C5 119.2(3) ?
O2 C11 O3 121.8(3) yes
O2 C11 C2 124.5(3) yes
O3 C11 C2 113.7(3) ?
O3 C12 H12A 109.5 ?
O3 C12 H12B 109.5 ?
H12A C12 H12B 109.5 ?
O3 C12 H12C 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 109.5 ?
O4 C13 C14 122.6(3) yes
O4 C13 C22 116.2(3) ?
C14 C13 C22 121.2(2) ?
C13 C14 C15 118.6(3) ?
C13 C14 C23 119.3(2) ?
C15 C14 C23 122.2(3) ?
C16 C15 C14 121.7(3) ?
C16 C15 H15 119.1 ?
C14 C15 H15 119.1 ?
C15 C16 C17 120.5(2) ?
C15 C16 H16 119.7 ?
C17 C16 H16 119.7 ?
C18 C17 C16 122.2(3) ?
C18 C17 C22 118.6(3) ?
C16 C17 C22 119.2(3) ?
C19 C18 C17 121.0(3) ?
C19 C18 H18 119.5 ?
C17 C18 H18 119.5 ?
C18 C19 C20 120.6(3) ?
C18 C19 H19 119.7 ?
C20 C19 H19 119.7 ?
C21 C20 C19 119.9(3) ?
C21 C20 H20 120.1 ?
C19 C20 H20 120.1 ?
C20 C21 C22 121.3(3) ?
C20 C21 H21 119.4 ?
C22 C21 H21 119.4 ?
C21 C22 C13 122.6(2) ?
C21 C22 C17 118.7(3) ?
C13 C22 C17 118.7(2) ?
O5 C23 O6 121.1(3) yes
O5 C23 C14 124.8(3) yes
O6 C23 C14 114.2(2) ?
O6 C24 H24A 109.5 ?
O6 C24 H24B 109.5 ?
H24A C24 H24B 109.5 ?
O6 C24 H24C 109.5 ?
H24A C24 H24C 109.5 ?
H24B C24 H24C 109.5 ?
C1 O1 H1 103(2) ?
C11 O3 C12 116.6(2) yes
C13 O4 H4 105(2) ?
C23 O6 C24 117.2(2) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.352(3) yes
C1 C2 1.383(4) ?
C1 C10 1.413(4) ?
C2 C3 1.420(4) ?
C2 C11 1.465(4) yes
C3 C4 1.343(4) ?
C3 H3 0.9300 ?
C4 C5 1.420(4) ?
C4 H4A 0.9300 ?
C5 C6 1.408(4) ?
C5 C10 1.417(4) ?
C6 C7 1.359(4) ?
C6 H6 0.9300 ?
C7 C8 1.401(4) ?
C7 H7 0.9300 ?
C8 C9 1.344(4) ?
C8 H8 0.9300 ?
C9 C10 1.414(4) ?
C9 H9 0.9300 ?
C11 O2 1.218(3) yes
C11 O3 1.333(3) yes
C12 O3 1.455(4) yes
C12 H12A 0.9600 ?
C12 H12B 0.9600 ?
C12 H12C 0.9600 ?
C13 O4 1.351(3) yes
C13 C14 1.385(4) ?
C13 C22 1.420(4) ?
C14 C15 1.422(4) ?
C14 C23 1.450(4) yes
C15 C16 1.353(4) ?
C15 H15 0.9300 ?
C16 C17 1.418(4) ?
C16 H16 0.9300 ?
C17 C18 1.403(4) ?
C17 C22 1.421(3) ?
C18 C19 1.359(4) ?
C18 H18 0.9300 ?
C19 C20 1.403(4) ?
C19 H19 0.9300 ?
C20 C21 1.352(4) ?
C20 H20 0.9300 ?
C21 C22 1.412(4) ?
C21 H21 0.9300 ?
C23 O5 1.225(3) yes
C23 O6 1.336(3) yes
C24 O6 1.440(4) yes
C24 H24A 0.9600 ?
C24 H24B 0.9600 ?
C24 H24C 0.9600 ?
O1 H1 0.81(3) ?
O4 H4 0.94(3) ?
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_publ_flag
O1 H1 O2 0.81(3) 1.87(3) 2.596(3) 149(3) yes
O4 H4 O5 0.94(3) 1.74(3) 2.594(3) 149(3) 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_publ_flag
O1 C1 C2 C3 -179.9(3) ?
C10 C1 C2 C3 0.5(4) ?
O1 C1 C2 C11 -1.4(4) ?
C10 C1 C2 C11 179.0(2) ?
C1 C2 C3 C4 0.1(4) ?
C11 C2 C3 C4 -178.3(3) ?
C2 C3 C4 C5 -0.5(5) ?
C3 C4 C5 C6 -179.0(3) ?
C3 C4 C5 C10 0.3(5) ?
C10 C5 C6 C7 0.7(5) ?
C4 C5 C6 C7 180.0(3) ?
C5 C6 C7 C8 0.0(5) ?
C6 C7 C8 C9 -0.3(5) ?
C7 C8 C9 C10 -0.1(5) ?
O1 C1 C10 C9 0.4(4) ?
C2 C1 C10 C9 -180.0(3) ?
O1 C1 C10 C5 179.7(2) yes
C2 C1 C10 C5 -0.8(4) ?
C8 C9 C10 C1 -180.0(3) ?
C8 C9 C10 C5 0.8(4) ?
C6 C5 C10 C1 179.7(3) ?
C4 C5 C10 C1 0.4(4) ?
C6 C5 C10 C9 -1.1(4) ?
C4 C5 C10 C9 179.6(3) ?
C1 C2 C11 O2 0.4(5) ?
C3 C2 C11 O2 178.8(3) yes
C1 C2 C11 O3 -179.2(2) ?
C3 C2 C11 O3 -0.8(4) ?
O4 C13 C14 C15 -178.7(2) ?
C22 C13 C14 C15 1.6(4) ?
O4 C13 C14 C23 0.7(4) ?
C22 C13 C14 C23 -179.0(2) ?
C13 C14 C15 C16 -0.7(4) ?
C23 C14 C15 C16 179.8(2) ?
C14 C15 C16 C17 0.1(4) ?
C15 C16 C17 C18 -179.4(3) ?
C15 C16 C17 C22 -0.3(4) ?
C16 C17 C18 C19 178.7(3) ?
C22 C17 C18 C19 -0.4(4) ?
C17 C18 C19 C20 0.1(4) ?
C18 C19 C20 C21 0.5(5) ?
C19 C20 C21 C22 -0.6(4) ?
C20 C21 C22 C13 -179.7(3) ?
C20 C21 C22 C17 0.3(4) ?
O4 C13 C22 C21 -1.5(4) ?
C14 C13 C22 C21 178.2(2) ?
O4 C13 C22 C17 178.5(2) yes
C14 C13 C22 C17 -1.7(4) ?
C18 C17 C22 C21 0.2(4) ?
C16 C17 C22 C21 -178.9(2) ?
C18 C17 C22 C13 -179.8(2) ?
C16 C17 C22 C13 1.1(4) ?
C13 C14 C23 O5 -1.6(4) ?
C15 C14 C23 O5 177.8(3) yes
C13 C14 C23 O6 179.0(2) ?
C15 C14 C23 O6 -1.6(4) ?
O2 C11 O3 C12 -0.6(4) ?
C2 C11 O3 C12 179.0(3) yes
O5 C23 O6 C24 -2.1(4) ?
C14 C23 O6 C24 177.2(2) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 63539
