#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:52:38 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301791 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/12/2001225.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_2001225
loop_
_publ_author_name
'Fitzgerald, L. J.'
'Gerkin, R. E.'
_publ_section_title
;
 Redetermination of the structures of 1-naphthoic acid and 2-naphthoic
 acid
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1952
_journal_page_last               1958
_journal_paper_doi               10.1107/S0108270193002641
_journal_volume                  49
_journal_year                    1993
_chemical_formula_sum            'C11 H8 O2'
_chemical_formula_weight         172.18
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_type_scat_source
; from Cromer & Waber (1974) for C and O atoms and from
Stewart, Davidson & Simpson (1965) for H atoms
;
_cell_angle_alpha                90.
_cell_angle_beta                 92.04(2)
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   6.906(3)
_cell_length_b                   3.842(5)
_cell_length_c                   30.958(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      15
_cell_measurement_theta_min      14
_cell_volume                     820.9(11)
_diffrn_measurement_device       'Rigaku AFC5S'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.013
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            2316
_diffrn_reflns_theta_max         27.5
_diffrn_standards_decay_%        +-2.0
_diffrn_standards_interval_count 150
_diffrn_standards_number         6
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.39
_exptl_crystal_description       plate
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.17
_refine_ls_extinction_coef       1.66E-6(64)
_refine_ls_extinction_method     'Zachariasen (1963, 1968)'
_refine_ls_goodness_of_fit_obs   1.93
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     151
_refine_ls_number_reflns         1050
_refine_ls_R_factor_obs          0.046
_refine_ls_shift/esd_max         <0.01
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      \s~F~^-2^
_refine_ls_wR_factor_obs         0.055
_reflns_number_observed          1050
_reflns_number_total             2148
_reflns_observed_criterion       I>3\s(I)
_cod_data_source_file            st1051.cif
_cod_data_source_block           st1051_structure_1_of_2
_cod_original_cell_volume        821.0(10)
_cod_database_code               2001225
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
O(1) .2289(3) .2164(7) .49220(6)
O(2) .0233(2) -.0576(6) .44819(5)
C(1) .3122(3) .1814(6) .41931(7)
C(2) .4883(4) .3222(8) .43165(8)
C(3) .6294(4) .3971(8) .40157(10)
C(4) .5921(4) .3300(8) .35948(9)
C(5) .3772(4) .1144(8) .29991(8)
C(6) .2056(4) -.0199(8) .28563(8)
C(7) .0613(4) -.0868(8) .31447(8)
C(8) .0899(4) -.0259(7) .35791(8)
C(9) .2675(3) .1107(6) .37461(7)
C(10) .4140(3) .1847(6) .34454(7)
C(11) .1739(3) .1022(7) .45374(7)
H(1) .122(4) .147(9) .5135(10)
H(2) .515(4) .363(7) .4598(8)
H(3) .756(4) .496(7) .4101(8)
H(4) .697(3) .381(7) .3351(8)
H(5) .483(3) .169(6) .2804(7)
H(6) .192(4) -.075(7) .2540(9)
H(7) -.064(4) -.182(7) .3032(8)
H(8) -.011(3) -.075(7) .3760(8)
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
C(1) C(2) C(3) 121.7(2) no
C(1) C(2) H(2) 119(2) no
C(1) C(9) C(8) 125.2(2) no
C(1) C(9) C(10) 117.3(2) no
C(1) C(11) O(1) 114.1(2) no
C(1) C(11) O(2) 124.8(2) no
C(2) C(3) C(4) 119.4(3) no
C(2) C(3) H(3) 122(2) no
H(2) C(2) C(3) 119(2) no
C(3) C(4) C(10) 121.8(2) no
C(3) C(4) H(4) 122.0(10) no
H(3) C(3) C(4) 118(2) no
C(4) C(10) C(9) 119.6(2) no
C(4) C(10) C(5) 121.1(2) no
H(4) C(4) C(10) 116.0(10) no
C(10) C(9) C(8) 117.4(2) no
C(10) C(5) C(6) 121.0(3) no
C(10) C(5) H(5) 116.0(10) no
C(15) C(6) C(7) 120.1(2) no
C(5) C(6) H(6) 117(2) no
H(5) C(5) C(6) 123.0(10) no
C(6) C(7) C(8) 121.2(3) no
C(6) C(7) H(7) 119(2) no
H(6) C(6) C(7) 123(2) no
C(7) C(8) C(9) 120.9(2) no
C(7) C(8) H(8) 118.0(10) no
H(7) C(7) C(8) 120(2) no
H(8) C(8) C(9) 121.0(10) no
C(9) C(1) C(11) 122.1(2) no
C(9) C(1) C(2) 120.1(2) no
C(9) C(10) C(5) 119.3(2) no
C(2) C(1) C(11) 117.8(2) no
O(2) C(11) O(1) 121.1(2) no
C(11) O(1) H(1) 108(2) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C(1) C(2) 1.373(3) no
C(2) C(3) 1.402(4) no
C(3) C(4) 1.344(4) no
C(4) C(10) 1.414(4) no
C(5) C(10) 1.422(3) no
C(5) C(6) 1.353(4) no
C(6) C(7) 1.386(4) no
C(7) C(8) 1.372(3) no
C(8) C(9) 1.415(3) no
C(9) C(10) 1.428(3) no
C(1) C(11) 1.488(3) no
C(11) O(1) 1.312(3) no
C(11) O(2) 1.214(3) no
O(1) H(2) 2.32(3) no
O(1) H(1) 1.04(3) no
O(2) H(8) 2.24(2) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 6847
