#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/79/2227948.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_2227948
loop_
_publ_author_name
'Souza, Bruno S.'
'Vitto, Ramon'
'Nome, Faruk'
'Kirby, Anthony J.'
'Bortoluzzi, Adailton J.'
_publ_section_title
;
 3-Acetoxy-2-naphthoic acid
;
_journal_coeditor_code           RK2238
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2848
_journal_paper_doi               10.1107/S1600536810040365
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H10 O4'
_chemical_formula_moiety         'C13 H10 O4'
_chemical_formula_sum            'C13 H10 O4'
_chemical_formula_weight         230.21
_chemical_name_systematic
;
3-Acetoxy-2-naphthoic acid
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.060(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.235(2)
_cell_length_b                   4.739(2)
_cell_length_c                   23.0873(16)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      18.45
_cell_measurement_theta_min      6.50
_cell_volume                     1099.0(5)
_computing_cell_refinement
'SET4 in CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'HELENA (Spek, 1996)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω-/2θ
_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  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            1999
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         1.80
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.256
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1950
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.1112
_refine_ls_R_factor_gt           0.0627
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1252P)²+0.1035P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1745
_refine_ls_wR_factor_ref         0.2039
_reflns_number_gt                1214
_reflns_number_total             1950
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rk2238.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2227948
_cod_database_fobs_code          2227948
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_disorder_assembly
_atom_site_disorder_group
C C1 0.5573(3) 0.3368(7) 0.18259(12) 0.0566(8) Uani d . 1 . .
H H1 0.6184 0.4763 0.1779 0.068 Uiso calc R 1 . .
C C2 0.4810(3) 0.2182(6) 0.13351(12) 0.0518(7) Uani d . 1 . .
C C3 0.3930(3) -0.0003(6) 0.14168(12) 0.0540(8) Uani d . 1 . .
C C4 0.3780(3) -0.0817(7) 0.19648(14) 0.0632(9) Uani d . 1 . .
H H4 0.3170 -0.2222 0.2006 0.076 Uiso calc R 1 . .
C C5 0.4544(3) 0.0454(7) 0.24728(13) 0.0599(8) Uani d . 1 . .
C C6 0.4428(3) -0.0331(9) 0.30541(14) 0.0737(10) Uani d . 1 . .
H H6 0.3804 -0.1680 0.3110 0.088 Uiso calc R 1 . .
C C7 0.5213(4) 0.0861(9) 0.35239(15) 0.0806(11) Uani d . 1 . .
H H7 0.5127 0.0308 0.3901 0.097 Uiso calc R 1 . .
C C8 0.6136(4) 0.2872(9) 0.34600(14) 0.0815(11) Uani d . 1 . .
H H8 0.6669 0.3659 0.3792 0.098 Uiso calc R 1 . .
C C9 0.6278(3) 0.3735(8) 0.29060(13) 0.0736(10) Uani d . 1 . .
H H9 0.6906 0.5097 0.2863 0.088 Uiso calc R 1 . .
C C10 0.5463(3) 0.2538(7) 0.24028(12) 0.0564(8) Uani d . 1 . .
C C11 0.4918(3) 0.3266(7) 0.07423(12) 0.0543(7) Uani d . 1 . .
C C12 0.2108(3) -0.0557(7) 0.06310(13) 0.0583(8) Uani d . 1 . .
C C13 0.1651(3) -0.2253(8) 0.00866(15) 0.0770(10) Uani d . 1 . .
H H13A 0.0772 -0.1662 -0.0098 0.115 Uiso calc R 1 . .
H H13B 0.1635 -0.4215 0.0188 0.115 Uiso calc R 1 . .
H H13C 0.2250 -0.1974 -0.0181 0.115 Uiso calc R 1 . .
O O1 0.4153(2) 0.2552(5) 0.02898(9) 0.0680(7) Uani d . 1 . .
O O2 0.5866(2) 0.5076(6) 0.07447(9) 0.0768(8) Uani d . 1 . .
H H2 0.5764 0.5907 0.0385 0.092 Uiso d R 1 . .
O O3 0.32733(19) -0.1555(4) 0.09356(9) 0.0623(6) Uani d . 1 . .
O O4 0.1549(2) 0.1389(6) 0.07911(10) 0.0802(8) Uani d . 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C10 . . 122.0(3) ?
C2 C1 H1 . . 119.0 ?
C10 C1 H1 . . 119.0 ?
C1 C2 C3 . . 118.0(3) ?
C1 C2 C11 . . 119.3(3) ?
C3 C2 C11 . . 122.7(3) ?
C4 C3 O3 . . 118.0(3) ?
C4 C3 C2 . . 121.5(3) ?
O3 C3 C2 . . 120.3(2) ?
C3 C4 C5 . . 120.6(3) ?
C3 C4 H4 . . 119.7 ?
C5 C4 H4 . . 119.7 ?
C10 C5 C4 . . 118.9(3) ?
C10 C5 C6 . . 118.4(3) ?
C4 C5 C6 . . 122.7(3) ?
C7 C6 C5 . . 120.5(4) ?
C7 C6 H6 . . 119.8 ?
C5 C6 H6 . . 119.8 ?
C6 C7 C8 . . 121.6(3) ?
C6 C7 H7 . . 119.2 ?
C8 C7 H7 . . 119.2 ?
C7 C8 C9 . . 120.3(3) ?
C7 C8 H8 . . 119.9 ?
C9 C8 H8 . . 119.9 ?
C8 C9 C10 . . 119.6(4) ?
C8 C9 H9 . . 120.2 ?
C10 C9 H9 . . 120.2 ?
C5 C10 C9 . . 119.6(3) ?
C5 C10 C1 . . 118.9(3) ?
C9 C10 C1 . . 121.5(3) ?
O1 C11 O2 . . 122.8(3) ?
O1 C11 C2 . . 122.8(3) ?
O2 C11 C2 . . 114.4(2) ?
O4 C12 O3 . . 122.9(3) ?
O4 C12 C13 . . 126.3(3) ?
O3 C12 C13 . . 110.7(3) ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C11 O2 H2 . . 109.2 ?
C12 O3 C3 . . 118.3(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.368(4) ?
C1 C10 . 1.414(4) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.409(4) ?
C2 C11 . 1.486(4) ?
C3 C4 . 1.359(4) ?
C3 O3 . 1.393(3) ?
C4 C5 . 1.413(4) ?
C4 H4 . 0.9300 ?
C5 C10 . 1.395(4) ?
C5 C6 . 1.419(4) ?
C6 C7 . 1.344(5) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.370(5) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.377(5) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.412(4) ?
C9 H9 . 0.9300 ?
C11 O1 . 1.227(3) ?
C11 O2 . 1.295(3) ?
C12 O4 . 1.181(4) ?
C12 O3 . 1.349(3) ?
C12 C13 . 1.490(4) ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
O2 H2 . 0.9071 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H2 O1 3_665 0.91 1.74 2.636(3) 170.7 y
C7 H7 O4 2_545 0.93 2.71 3.368(5) 128 y
C13 H13B O4 1_545 0.96 2.52 3.435(5) 160 y
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C10 C1 C2 C3 . . . . -2.4(4) ?
C10 C1 C2 C11 . . . . 176.4(3) ?
C1 C2 C3 C4 . . . . 3.6(4) ?
C11 C2 C3 C4 . . . . -175.2(3) ?
C1 C2 C3 O3 . . . . -170.7(2) ?
C11 C2 C3 O3 . . . . 10.5(4) ?
O3 C3 C4 C5 . . . . 172.3(2) ?
C2 C3 C4 C5 . . . . -2.1(5) ?
C3 C4 C5 C10 . . . . -0.6(5) ?
C3 C4 C5 C6 . . . . -179.7(3) ?
C10 C5 C6 C7 . . . . -1.7(5) ?
C4 C5 C6 C7 . . . . 177.4(3) ?
C5 C6 C7 C8 . . . . 0.5(6) ?
C6 C7 C8 C9 . . . . 0.3(6) ?
C7 C8 C9 C10 . . . . 0.1(5) ?
C4 C5 C10 C9 . . . . -177.1(3) ?
C6 C5 C10 C9 . . . . 2.1(4) ?
C4 C5 C10 C1 . . . . 1.8(4) ?
C6 C5 C10 C1 . . . . -179.1(3) ?
C8 C9 C10 C5 . . . . -1.3(5) ?
C8 C9 C10 C1 . . . . 179.8(3) ?
C2 C1 C10 C5 . . . . -0.3(4) ?
C2 C1 C10 C9 . . . . 178.6(3) ?
C1 C2 C11 O1 . . . . -170.7(3) ?
C3 C2 C11 O1 . . . . 8.0(5) ?
C1 C2 C11 O2 . . . . 7.7(4) ?
C3 C2 C11 O2 . . . . -173.5(2) ?
O4 C12 O3 C3 . . . . -8.7(4) ?
C13 C12 O3 C3 . . . . 171.9(3) ?
C4 C3 O3 C12 . . . . 98.6(3) ?
C2 C3 O3 C12 . . . . -86.8(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 202217
