#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/19/2221996.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_2221996
loop_
_publ_author_name
'Jumpathong, Juangjun'
'Retailleau, Pascal'
'Abdalla, Muna Ali'
'Ouazzani, Jamal'
'Lumyong, Saisamorn'
_publ_section_title
;
 2-Butyl-5-pentylbenzene-1,3-diol
;
_journal_coeditor_code           DN2455
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1366
_journal_paper_doi               10.1107/S1600536809018820
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H24 O2'
_chemical_formula_moiety         'C15 H24 O2'
_chemical_formula_sum            'C15 H24 O2'
_chemical_formula_weight         236.34
_chemical_melting_point          364
_chemical_name_common            stemphol
_chemical_name_systematic
;
2-Butyl-5-pentylbenzene-1,3-diol
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.120(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.654(2)
_cell_length_b                   25.450(5)
_cell_length_c                   12.790(4)
_cell_measurement_reflns_used    2700
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.350
_cell_measurement_theta_min      0.407
_cell_volume                     1439.8(8)
_computing_cell_refinement       'DENZO  (Otwinowski & Minor, 1997)'
_computing_data_collection
;
DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1999)
;
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
;
PLATON (Spek, 2009) and Mercury (Macrae et al.,  2006)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2009)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008) and CrystalBuilder (Welter, 2006)
;
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD'
_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     0.71069
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0413
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15852
_diffrn_reflns_theta_full        25.33
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_min         2.32
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.090
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.155
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2631
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0478
_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)+(0.0625P)²+0.1805P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1313
_reflns_number_gt                1703
_reflns_number_total             2631
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2455.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2221996
_cod_database_fobs_code          2221996
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 O1 0.0951(3) 0.27129(5) 0.28490(10) 0.0555(4) Uani d . 1 . .
H H1 0.2648 0.2719 0.3299 0.083 Uiso calc R 1 . .
O O2 -0.2986(2) 0.22721(5) -0.09324(9) 0.0517(4) Uani d . 1 . .
H H2 -0.2074 0.2253 -0.1386 0.077 Uiso calc R 1 . .
C C1 -0.1145(3) 0.24879(6) 0.09661(13) 0.0358(4) Uani d . 1 . .
C C2 -0.1012(3) 0.21631(7) 0.01107(13) 0.0383(4) Uani d . 1 . .
C C3 0.0994(4) 0.17495(7) 0.02531(14) 0.0428(4) Uani d . 1 . .
H H3 0.1000 0.1542 -0.0345 0.051 Uiso calc R 1 . .
C C4 0.3006(3) 0.16426(7) 0.12888(14) 0.0414(4) Uani d . 1 . .
C C5 0.2925(3) 0.19620(7) 0.21530(14) 0.0432(5) Uani d . 1 . .
H H5 0.4233 0.1896 0.2855 0.052 Uiso calc R 1 . .
C C6 0.0935(3) 0.23774(7) 0.19898(13) 0.0394(4) Uani d . 1 . .
C C7 -0.3211(4) 0.29564(7) 0.07705(15) 0.0454(5) Uani d . 1 . .
H H7A -0.3674 0.3038 0.1441 0.054 Uiso calc R 1 . .
H H7B -0.5092 0.2871 0.0207 0.054 Uiso calc R 1 . .
C C8 -0.1801(4) 0.34346(7) 0.04135(17) 0.0557(5) Uani d . 1 . .
H H8A 0.0020 0.3528 0.0999 0.067 Uiso calc R 1 . .
H H8B -0.1210 0.3341 -0.0226 0.067 Uiso calc R 1 . .
C C9 -0.3832(5) 0.39095(8) 0.0136(2) 0.0756(7) Uani d . 1 . .
H H9A -0.5625 0.3822 -0.0468 0.091 Uiso calc R 1 . .
H H9B -0.4472 0.3999 0.0766 0.091 Uiso calc R 1 . .
C C10 -0.2332(6) 0.43810(9) -0.0182(3) 0.1069(10) Uani d . 1 . .
H H10A -0.0721 0.4500 0.0445 0.160 Uiso calc R 1 . .
H H10B -0.3790 0.4657 -0.0430 0.160 Uiso calc R 1 . .
H H10C -0.1529 0.4286 -0.0762 0.160 Uiso calc R 1 . .
C C11 0.5085(4) 0.11754(7) 0.14655(16) 0.0523(5) Uani d . 1 . .
H H11A 0.6758 0.1228 0.2134 0.063 Uiso calc R 1 . .
H H11B 0.5910 0.1151 0.0858 0.063 Uiso calc R 1 . .
C C12 0.3515(4) 0.06650(7) 0.15543(18) 0.0604(6) Uani d . 1 . .
H H12A 0.1767 0.0628 0.0905 0.073 Uiso calc R 1 . .
H H12B 0.2783 0.0687 0.2185 0.073 Uiso calc R 1 . .
C C13 0.5435(4) 0.01760(7) 0.16697(17) 0.0594(5) Uani d . 1 . .
H H13A 0.6171 0.0153 0.1040 0.071 Uiso calc R 1 . .
H H13B 0.7178 0.0211 0.2322 0.071 Uiso calc R 1 . .
C C14 0.3833(5) -0.03251(8) 0.1752(2) 0.0848(8) Uani d . 1 . .
H H14A 0.3137 -0.0304 0.2391 0.102 Uiso calc R 1 . .
H H14B 0.2060 -0.0354 0.1109 0.102 Uiso calc R 1 . .
C C15 0.5672(6) -0.08146(9) 0.1840(2) 0.0970(9) Uani d . 1 . .
H H15A 0.6319 -0.0848 0.1200 0.145 Uiso calc R 1 . .
H H15B 0.4468 -0.1114 0.1892 0.145 Uiso calc R 1 . .
H H15C 0.7409 -0.0796 0.2485 0.145 Uiso calc R 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
C6 O1 H1 . . 109.5 ?
C2 O2 H2 . . 109.5 ?
C2 C1 C6 . . 115.59(15) ?
C2 C1 C7 . . 121.63(14) ?
C6 C1 C7 . . 122.55(15) ?
C3 C2 C1 . . 122.97(15) ?
C3 C2 O2 . . 119.73(15) ?
C1 C2 O2 . . 117.29(14) ?
C2 C3 C4 . . 120.13(16) ?
C2 C3 H3 . . 119.9 ?
C4 C3 H3 . . 119.9 ?
C5 C4 C3 . . 117.98(15) ?
C5 C4 C11 . . 121.38(16) ?
C3 C4 C11 . . 120.57(17) ?
C6 C5 C4 . . 120.95(15) ?
C6 C5 H5 . . 119.5 ?
C4 C5 H5 . . 119.5 ?
C5 C6 O1 . . 120.90(14) ?
C5 C6 C1 . . 122.35(16) ?
O1 C6 C1 . . 116.74(14) ?
C1 C7 C8 . . 111.85(14) ?
C1 C7 H7A . . 109.2 ?
C8 C7 H7A . . 109.2 ?
C1 C7 H7B . . 109.2 ?
C8 C7 H7B . . 109.2 ?
H7A C7 H7B . . 107.9 ?
C9 C8 C7 . . 114.57(16) ?
C9 C8 H8A . . 108.6 ?
C7 C8 H8A . . 108.6 ?
C9 C8 H8B . . 108.6 ?
C7 C8 H8B . . 108.6 ?
H8A C8 H8B . . 107.6 ?
C10 C9 C8 . . 113.16(18) ?
C10 C9 H9A . . 108.9 ?
C8 C9 H9A . . 108.9 ?
C10 C9 H9B . . 108.9 ?
C8 C9 H9B . . 108.9 ?
H9A C9 H9B . . 107.8 ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C4 C11 C12 . . 112.77(14) ?
C4 C11 H11A . . 109.0 ?
C12 C11 H11A . . 109.0 ?
C4 C11 H11B . . 109.0 ?
C12 C11 H11B . . 109.0 ?
H11A C11 H11B . . 107.8 ?
C11 C12 C13 . . 115.46(16) ?
C11 C12 H12A . . 108.4 ?
C13 C12 H12A . . 108.4 ?
C11 C12 H12B . . 108.4 ?
C13 C12 H12B . . 108.4 ?
H12A C12 H12B . . 107.5 ?
C14 C13 C12 . . 114.58(17) ?
C14 C13 H13A . . 108.6 ?
C12 C13 H13A . . 108.6 ?
C14 C13 H13B . . 108.6 ?
C12 C13 H13B . . 108.6 ?
H13A C13 H13B . . 107.6 ?
C15 C14 C13 . . 115.4(2) ?
C15 C14 H14A . . 108.4 ?
C13 C14 H14A . . 108.4 ?
C15 C14 H14B . . 108.4 ?
C13 C14 H14B . . 108.4 ?
H14A C14 H14B . . 107.5 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
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
O1 C6 . 1.3899(19) ?
O1 H1 . 0.8200 ?
O2 C2 . 1.3924(18) ?
O2 H2 . 0.8200 ?
C1 C2 . 1.388(2) ?
C1 C6 . 1.394(2) ?
C1 C7 . 1.503(2) ?
C2 C3 . 1.381(2) ?
C3 C4 . 1.391(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.382(2) ?
C4 C11 . 1.505(2) ?
C5 C6 . 1.378(2) ?
C5 H5 . 0.9300 ?
C7 C8 . 1.519(3) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.507(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.506(3) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 C12 . 1.512(3) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C13 . 1.512(3) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C14 . 1.497(3) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C15 . 1.496(3) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
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
O1 H1 O2 4_666 0.82 1.963 2.767(2) 166.63 y
O2 H2 O1 4_565 0.82 1.951 2.750(2) 164.82 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
C6 C1 C2 C3 . . . . 1.2(2) ?
C7 C1 C2 C3 . . . . 175.85(15) ?
C6 C1 C2 O2 . . . . -177.88(13) ?
C7 C1 C2 O2 . . . . -3.2(2) ?
C1 C2 C3 C4 . . . . -0.1(2) ?
O2 C2 C3 C4 . . . . 179.01(14) ?
C2 C3 C4 C5 . . . . -0.2(2) ?
C2 C3 C4 C11 . . . . 176.65(15) ?
C3 C4 C5 C6 . . . . -0.8(2) ?
C11 C4 C5 C6 . . . . -177.58(15) ?
C4 C5 C6 O1 . . . . -177.00(15) ?
C4 C5 C6 C1 . . . . 2.0(2) ?
C2 C1 C6 C5 . . . . -2.2(2) ?
C7 C1 C6 C5 . . . . -176.77(15) ?
C2 C1 C6 O1 . . . . 176.89(14) ?
C7 C1 C6 O1 . . . . 2.3(2) ?
C2 C1 C7 C8 . . . . -83.9(2) ?
C6 C1 C7 C8 . . . . 90.4(2) ?
C1 C7 C8 C9 . . . . 176.41(17) ?
C7 C8 C9 C10 . . . . 178.26(19) ?
C5 C4 C11 C12 . . . . 98.0(2) ?
C3 C4 C11 C12 . . . . -78.7(2) ?
C4 C11 C12 C13 . . . . 176.76(17) ?
C11 C12 C13 C14 . . . . -179.8(2) ?
C12 C13 C14 C15 . . . . 178.6(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 149454
