Crystal structure of olivetolic acid: a natural product from <i>Cetrelia sanguinea</i> (Schaer.)
Ismed, Friardi; Farhan, Aulia; Bakhtiar, Amri; Zaini, Erizal; Nugraha, Yuda Prasetya; Dwichandra Putra, Okky; Uekusa, Hidehiro; Acta Crystallographica Section E 72 (2016) 1587–1589; doi:10.1107/S2056989016016273

data_2241887
_publ_section_title
;
 Crystal structure of olivetolic acid: a natural product from <i>Cetrelia
 sanguinea</i> (Schaer.)
;
_journal_coeditor_code           HB7614
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1587
_journal_page_last               1589
_journal_paper_doi               10.1107/S2056989016016273
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C12 H16 O4'
_chemical_formula_moiety         'C12 H16 O4'
_chemical_formula_sum            'C12 H16 O4'
_chemical_formula_weight         224.25
_chemical_name_common            'olivetolic acid'
_chemical_name_systematic
;
2,4-Dihydroxy-6-pentylbenzoic acid
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   none
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 103.538(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2527(8)
_cell_length_b                   4.7524(3)
_cell_length_c                   17.6489(11)
_cell_measurement_reflns_used    12628
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      3.6
_cell_volume                     1162.22(12)
_computing_cell_refinement
;
PROCESS-AUTO (Rigaku, 1998)
;
_computing_data_collection
;
PROCESS-AUTO (Rigaku, 1998)
;
_computing_data_reduction
;
PROCESS-AUTO (Rigaku, 1998)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS2014 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID II'
_diffrn_measurement_method       \w-scan
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12627
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         68.231
_diffrn_reflns_theta_min         3.600
_exptl_absorpt_coefficient_mu    0.793
_exptl_absorpt_correction_T_max  0.924
_exptl_absorpt_correction_T_min  0.789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(ABSCOR; Higashi, 1995)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.121
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.183
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2087
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0446
_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/[\s^2^(Fo^2^)+(0.0808P)^2^+0.1676P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1293
_refine_ls_wR_factor_ref         0.1359
_reflns_number_gt                1762
_reflns_number_total             2087
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb7614sup1.cif
_cod_data_source_block           I
_cod_database_code               2241887
_cod_database_fobs_code          2241887
_shelx_estimated_absorpt_t_min   0.910
_shelx_estimated_absorpt_t_max   0.925
_shelx_hkl_checksum              43872
_shelx_res_checksum              39073