#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/43/2224352.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_2224352
loop_
_publ_author_name
'Lima, Carlos F. R. A. C.'
'Gomes, Ligia R.'
'Santos, Luís M. N. B. F.'
'Low, John Nicolson'
_publ_section_title
;
 4-(1-Naphthyl)benzoic acid
;
_journal_coeditor_code           LH2945
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3037
_journal_paper_doi               10.1107/S1600536809046339
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C17 H12 O2'
_chemical_formula_moiety         'C17 H12 O2'
_chemical_formula_sum            'C17 H12 O2'
_chemical_formula_weight         248.27
_chemical_melting_point          509
_chemical_name_systematic
;
4-(1-Naphthyl)benzoic acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 99.323(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.8972(6)
_cell_length_b                   40.511(6)
_cell_length_c                   7.6106(12)
_cell_measurement_reflns_used    1563
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.44
_cell_measurement_theta_min      6.33
_cell_volume                     1185.7(3)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) and PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       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  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_k_max       50
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4700
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.44
_diffrn_reflns_theta_min         2.89
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9982
_exptl_absorpt_correction_T_min  0.9734
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.169
_refine_ls_extinction_coef       0.008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2412
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0443
_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)+(0.0453P)²+0.4999P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1074
_reflns_number_gt                1954
_reflns_number_total             2412
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2945.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2224352
_cod_database_fobs_code          2224352
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_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
O O41 0.5693(4) 0.50335(3) 0.73150(17) 0.0320(3) Uani d . 1 . .
H H41 0.4832 0.4923 0.6419 0.048 Uiso d PR 0.62(3) A -1
O O42 0.7354(4) 0.53531(3) 0.52203(16) 0.0330(3) Uani d . 1 . .
H H42 0.6502 0.5202 0.4440 0.050 Uiso d PR 0.38(3) A -2
C C1 1.1807(4) 0.62769(4) 1.2149(2) 0.0187(4) Uani d . 1 . .
C C2 1.3777(4) 0.61873(4) 1.3748(2) 0.0214(4) Uani d . 1 . .
H H2 1.4358 0.5961 1.3961 0.026 Uiso calc R 1 . .
C C3 1.4950(4) 0.64219(5) 1.5074(2) 0.0248(4) Uani d . 1 . .
H H3 1.6296 0.6353 1.6166 0.030 Uiso calc R 1 . .
C C4 1.4159(5) 0.67478(5) 1.4795(2) 0.0260(4) Uani d . 1 . .
H H4 1.5015 0.6905 1.5683 0.031 Uiso calc R 1 . .
C C5 1.1179(5) 0.71913(4) 1.2917(2) 0.0266(4) Uani d . 1 . .
H H5 1.2060 0.7349 1.3797 0.032 Uiso calc R 1 . .
C C6 0.9075(5) 0.72919(4) 1.1408(2) 0.0288(4) Uani d . 1 . .
H H6 0.8491 0.7519 1.1242 0.035 Uiso calc R 1 . .
C C7 0.7765(5) 0.70599(4) 1.0094(2) 0.0267(4) Uani d . 1 . .
H H7 0.6281 0.7131 0.9047 0.032 Uiso calc R 1 . .
C C8 0.8613(4) 0.67326(4) 1.0313(2) 0.0224(4) Uani d . 1 . .
H H8 0.7689 0.6579 0.9414 0.027 Uiso calc R 1 . .
C C9 1.2078(4) 0.68535(4) 1.3196(2) 0.0216(4) Uani d . 1 . .
C C10 1.0846(4) 0.66168(4) 1.1855(2) 0.0190(4) Uani d . 1 . .
C C11 1.0745(4) 0.60175(4) 1.0782(2) 0.0180(4) Uani d . 1 . .
C C12 1.1205(4) 0.60601(4) 0.9008(2) 0.0197(4) Uani d . 1 . .
H H12 1.2256 0.6257 0.8670 0.024 Uiso calc R 1 . .
C C13 1.0158(4) 0.58211(4) 0.7744(2) 0.0196(4) Uani d . 1 . .
H H13 1.0497 0.5854 0.6548 0.024 Uiso calc R 1 . .
C C14 0.8601(4) 0.55312(4) 0.8215(2) 0.0192(4) Uani d . 1 . .
C C15 0.8267(4) 0.54788(4) 0.9991(2) 0.0209(4) Uani d . 1 . .
H H15 0.7294 0.5278 1.0334 0.025 Uiso calc R 1 . .
C C16 0.9353(4) 0.57188(4) 1.1253(2) 0.0203(4) Uani d . 1 . .
H H16 0.9147 0.5680 1.2462 0.024 Uiso calc R 1 . .
C C41 0.7169(4) 0.52934(4) 0.6815(2) 0.0215(4) 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
C41 O41 H41 . . 109.6 ?
C41 O42 H42 . . 116.4 ?
C2 C1 C10 . . 118.95(15) ?
C2 C1 C11 . . 118.87(15) ?
C10 C1 C11 . . 122.17(14) ?
C1 C2 C3 . . 121.67(16) ?
C1 C2 H2 . . 119.2 ?
C3 C2 H2 . . 119.2 ?
C4 C3 C2 . . 120.18(16) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
C3 C4 C9 . . 120.68(16) ?
C3 C4 H4 . . 119.7 ?
C9 C4 H4 . . 119.7 ?
C6 C5 C9 . . 121.00(17) ?
C6 C5 H5 . . 119.5 ?
C9 C5 H5 . . 119.5 ?
C5 C6 C7 . . 119.97(17) ?
C5 C6 H6 . . 120.0 ?
C7 C6 H6 . . 120.0 ?
C8 C7 C6 . . 120.50(17) ?
C8 C7 H7 . . 119.8 ?
C6 C7 H7 . . 119.8 ?
C7 C8 C10 . . 121.51(16) ?
C7 C8 H8 . . 119.2 ?
C10 C8 H8 . . 119.2 ?
C4 C9 C5 . . 120.89(16) ?
C4 C9 C10 . . 119.45(16) ?
C5 C9 C10 . . 119.66(16) ?
C8 C10 C9 . . 117.32(15) ?
C8 C10 C1 . . 123.64(15) ?
C9 C10 C1 . . 119.00(15) ?
C16 C11 C12 . . 118.02(15) ?
C16 C11 C1 . . 120.51(14) ?
C12 C11 C1 . . 121.44(14) ?
C13 C12 C11 . . 121.06(15) ?
C13 C12 H12 . . 119.5 ?
C11 C12 H12 . . 119.5 ?
C12 C13 C14 . . 120.24(15) ?
C12 C13 H13 . . 119.9 ?
C14 C13 H13 . . 119.9 ?
C13 C14 C15 . . 119.33(15) ?
C13 C14 C41 . . 119.53(14) ?
C15 C14 C41 . . 121.06(15) ?
C16 C15 C14 . . 119.96(15) ?
C16 C15 H15 . . 120.0 ?
C14 C15 H15 . . 120.0 ?
C15 C16 C11 . . 121.24(14) ?
C15 C16 H16 . . 119.4 ?
C11 C16 H16 . . 119.4 ?
O42 C41 O41 . . 122.96(15) ?
O42 C41 C14 . . 119.94(15) ?
O41 C41 C14 . . 117.08(14) ?
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
O41 C41 . 1.286(2) ?
O41 H41 . 0.8400 ?
O42 C41 . 1.251(2) ?
O42 H42 . 0.8806 ?
C1 C2 . 1.379(2) ?
C1 C10 . 1.435(2) ?
C1 C11 . 1.489(2) ?
C2 C3 . 1.407(2) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.365(3) ?
C3 H3 . 0.9500 ?
C4 C9 . 1.415(2) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.361(3) ?
C5 C9 . 1.420(2) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.407(3) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.370(2) ?
C7 H7 . 0.9500 ?
C8 C10 . 1.423(2) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.426(2) ?
C11 C16 . 1.396(2) ?
C11 C12 . 1.401(2) ?
C12 C13 . 1.379(2) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.395(2) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.395(2) ?
C14 C41 . 1.477(2) ?
C15 C16 . 1.384(2) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
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
O41 H41 O42 3_666 0.84 1.79 2.6161(18) 170 y
O42 H42 O41 3_666 0.88 1.75 2.6161(18) 168 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 . . . . -1.9(2) ?
C11 C1 C2 C3 . . . . 178.11(14) ?
C1 C2 C3 C4 . . . . -0.3(3) ?
C2 C3 C4 C9 . . . . 1.7(3) ?
C9 C5 C6 C7 . . . . -0.2(3) ?
C5 C6 C7 C8 . . . . -0.5(3) ?
C6 C7 C8 C10 . . . . -0.5(3) ?
C3 C4 C9 C5 . . . . 178.49(16) ?
C3 C4 C9 C10 . . . . -1.0(2) ?
C6 C5 C9 C4 . . . . -177.62(16) ?
C6 C5 C9 C10 . . . . 1.9(2) ?
C7 C8 C10 C9 . . . . 2.1(2) ?
C7 C8 C10 C1 . . . . 179.89(15) ?
C4 C9 C10 C8 . . . . 176.77(15) ?
C5 C9 C10 C8 . . . . -2.7(2) ?
C4 C9 C10 C1 . . . . -1.2(2) ?
C5 C9 C10 C1 . . . . 179.34(15) ?
C2 C1 C10 C8 . . . . -175.23(15) ?
C11 C1 C10 C8 . . . . 4.8(2) ?
C2 C1 C10 C9 . . . . 2.6(2) ?
C11 C1 C10 C9 . . . . -177.44(14) ?
C2 C1 C11 C16 . . . . 46.9(2) ?
C10 C1 C11 C16 . . . . -133.14(16) ?
C2 C1 C11 C12 . . . . -131.12(17) ?
C10 C1 C11 C12 . . . . 48.9(2) ?
C16 C11 C12 C13 . . . . 3.1(2) ?
C1 C11 C12 C13 . . . . -178.82(15) ?
C11 C12 C13 C14 . . . . 0.2(2) ?
C12 C13 C14 C15 . . . . -3.0(2) ?
C12 C13 C14 C41 . . . . 173.74(15) ?
C13 C14 C15 C16 . . . . 2.5(2) ?
C41 C14 C15 C16 . . . . -174.24(15) ?
C14 C15 C16 C11 . . . . 0.9(2) ?
C12 C11 C16 C15 . . . . -3.7(2) ?
C1 C11 C16 C15 . . . . 178.25(15) ?
C13 C14 C41 O42 . . . . -0.1(2) ?
C15 C14 C41 O42 . . . . 176.61(17) ?
C13 C14 C41 O41 . . . . -178.49(15) ?
C15 C14 C41 O41 . . . . -1.8(2) ?
