#------------------------------------------------------------------------------
#$Date: 2008-02-08 10:23:56 +0000 (Fri, 08 Feb 2008) $
#$Revision: 101 $
#$URL: svn://www.crystallography.net/cod/cif/2/2203694.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_2203694
loop_
_publ_author_name
'Abdelhak, Ettahiri'
'Mostafa, Abboudi'
'Merle, Daphne'
'Perrin, Monique'
'Thozet, Alain'
_publ_section_title
;
4-(2-Phenylisopropyl)phenol
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica, Section E'
_journal_page_first              o954
_journal_page_last               o955
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C15 H16 O'
_chemical_formula_moiety         'C15 H16 O'
_chemical_formula_sum            'C15 H16 O'
_chemical_formula_weight         212.28
_chemical_name_common            paracumylphenol
_chemical_name_systematic
;
4-(2-phenylisopropyl)phenol
;
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_H-M   'R -3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   30.989(4)
_cell_length_b                   30.989(4)
_cell_length_c                   6.5000(10)
_cell_measurement_reflns_used    8097
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.878
_cell_measurement_theta_min      1.018
_cell_volume                     5405.5(13)
_computing_cell_refinement       'HKL SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius BV, 1999)'
_computing_data_reduction
'HKL SCALEPACK and DENZO (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 1999)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0423
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2855
_diffrn_reflns_theta_full        27.85
_diffrn_reflns_theta_max         27.85
_diffrn_reflns_theta_min         3.48
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.9893
_exptl_absorpt_correction_T_min  0.9719
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2052
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.217
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2855
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.942
_refine_ls_R_factor_all          0.0872
_refine_ls_R_factor_gt           0.0493
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0636P)^2^+5.893P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1285
_reflns_number_gt                1948
_reflns_number_total             2855
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    ac6084.cif
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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_
_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_type_symbol
O1 0.34804(4) 0.03489(4) 0.01722(16) 0.0336(3) Uani d . 1 O
H1 0.3351 0.0193 -0.0902 0.050 Uiso calc R 1 H
C1 0.36952(5) 0.08549(6) -0.0195(2) 0.0268(3) Uani d . 1 C
C2 0.39345(6) 0.11810(6) 0.1415(2) 0.0287(4) Uani d . 1 C
H2 0.3958 0.1059 0.2708 0.034 Uiso calc R 1 H
C3 0.41382(6) 0.16878(6) 0.1110(2) 0.0283(4) Uani d . 1 C
H3 0.4296 0.1906 0.2218 0.034 Uiso calc R 1 H
C4 0.41168(5) 0.18850(6) -0.0795(2) 0.0268(3) Uani d . 1 C
C5 0.38846(6) 0.15488(6) -0.2388(2) 0.0311(4) Uani d . 1 C
H5 0.3868 0.1670 -0.3696 0.037 Uiso calc R 1 H
C6 0.36758(6) 0.10389(6) -0.2103(2) 0.0316(4) Uani d . 1 C
H6 0.3521 0.0819 -0.3210 0.038 Uiso calc R 1 H
C7 0.43124(6) 0.24464(6) -0.1009(2) 0.0290(4) Uani d . 1 C
C8 0.48275(6) 0.27424(6) -0.0007(2) 0.0261(3) Uani d . 1 C
C9 0.52031(6) 0.26461(6) -0.0604(2) 0.0281(3) Uani d . 1 C
H9 0.5130 0.2388 -0.1547 0.034 Uiso calc R 1 H
C10 0.56813(6) 0.29222(6) 0.0165(2) 0.0312(4) Uani d . 1 C
H10 0.5930 0.2852 -0.0262 0.037 Uiso calc R 1 H
C11 0.57953(6) 0.33019(6) 0.1564(2) 0.0338(4) Uani d . 1 C
H11 0.6122 0.3494 0.2067 0.041 Uiso calc R 1 H
C12 0.54276(7) 0.33956(6) 0.2211(2) 0.0363(4) Uani d . 1 C
H12 0.5501 0.3647 0.3185 0.044 Uiso calc R 1 H
C13 0.49467(7) 0.31187(6) 0.1426(2) 0.0338(4) Uani d . 1 C
H13 0.4699 0.3187 0.1873 0.041 Uiso calc R 1 H
C14 0.43700(7) 0.26118(6) -0.3281(2) 0.0365(4) Uani d . 1 C
H14A 0.4046 0.2446 -0.3946 0.055 Uiso calc R 1 H
H14B 0.4592 0.2523 -0.3978 0.055 Uiso calc R 1 H
H14C 0.4508 0.2970 -0.3347 0.055 Uiso calc R 1 H
C15 0.39263(7) 0.25528(7) 0.0002(3) 0.0393(4) Uani d . 1 C
H15A 0.3910 0.2485 0.1465 0.059 Uiso calc R 1 H
H15B 0.3602 0.2341 -0.0612 0.059 Uiso calc R 1 H
H15C 0.4023 0.2900 -0.0210 0.059 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0369(7) 0.0304(6) 0.0304(6) 0.0145(5) -0.0064(5) 0.0001(5)
C1 0.0223(8) 0.0298(8) 0.0289(7) 0.0136(7) -0.0001(6) 0.0020(6)
C2 0.0265(8) 0.0365(9) 0.0222(7) 0.0150(7) -0.0014(6) 0.0046(6)
C3 0.0253(8) 0.0332(9) 0.0229(7) 0.0121(7) -0.0019(6) -0.0011(6)
C4 0.0226(8) 0.0327(9) 0.0260(7) 0.0144(7) 0.0013(6) 0.0019(6)
C5 0.0357(9) 0.0363(9) 0.0226(7) 0.0189(8) -0.0029(6) 0.0027(6)
C6 0.0340(9) 0.0358(9) 0.0247(8) 0.0172(8) -0.0080(6) -0.0041(6)
C7 0.0315(9) 0.0320(9) 0.0264(8) 0.0181(7) -0.0003(6) 0.0016(6)
C8 0.0308(8) 0.0254(8) 0.0228(7) 0.0146(7) 0.0023(6) 0.0034(6)
C9 0.0319(8) 0.0262(8) 0.0242(7) 0.0131(7) 0.0009(6) -0.0012(6)
C10 0.0299(9) 0.0329(9) 0.0292(8) 0.0146(7) 0.0032(6) 0.0036(6)
C11 0.0350(9) 0.0278(9) 0.0305(8) 0.0096(7) -0.0051(7) 0.0022(7)
C12 0.0498(11) 0.0274(9) 0.0297(8) 0.0178(8) -0.0053(7) -0.0048(7)
C13 0.0435(10) 0.0348(9) 0.0293(8) 0.0242(8) 0.0017(7) -0.0015(7)
C14 0.0414(10) 0.0368(10) 0.0313(9) 0.0196(8) -0.0032(7) 0.0055(7)
C15 0.0364(10) 0.0468(11) 0.0431(10) 0.0271(9) 0.0009(7) 0.0010(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.3838(18)
O1 H1 0.8300
C1 C6 1.379(2)
C1 C2 1.385(2)
C2 C3 1.383(2)
C2 H2 0.9400
C3 C4 1.397(2)
C3 H3 0.9400
C4 C5 1.388(2)
C4 C7 1.536(2)
C5 C6 1.388(2)
C5 H5 0.9400
C6 H6 0.9400
C7 C8 1.533(2)
C7 C15 1.538(2)
C7 C14 1.544(2)
C8 C13 1.390(2)
C8 C9 1.394(2)
C9 C10 1.382(2)
C9 H9 0.9400
C10 C11 1.386(2)
C10 H10 0.9400
C11 C12 1.375(2)
C11 H11 0.9400
C12 C13 1.392(2)
C12 H12 0.9400
C13 H13 0.9400
C14 H14A 0.9700
C14 H14B 0.9700
C14 H14C 0.9700
C15 H15A 0.9700
C15 H15B 0.9700
C15 H15C 0.9700
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O1 H1 109.5
C6 C1 O1 121.89(14)
C6 C1 C2 119.75(15)
O1 C1 C2 118.36(13)
C3 C2 C1 119.62(13)
C3 C2 H2 120.2
C1 C2 H2 120.2
C2 C3 C4 121.95(14)
C2 C3 H3 119.0
C4 C3 H3 119.0
C5 C4 C3 116.94(14)
C5 C4 C7 123.08(13)
C3 C4 C7 119.83(13)
C4 C5 C6 121.78(13)
C4 C5 H5 119.1
C6 C5 H5 119.1
C1 C6 C5 119.92(14)
C1 C6 H6 120.0
C5 C6 H6 120.0
C8 C7 C4 110.03(12)
C8 C7 C15 112.26(13)
C4 C7 C15 107.18(13)
C8 C7 C14 107.16(13)
C4 C7 C14 112.16(13)
C15 C7 C14 108.10(13)
C13 C8 C9 117.78(15)
C13 C8 C7 123.17(14)
C9 C8 C7 119.00(13)
C10 C9 C8 121.25(14)
C10 C9 H9 119.4
C8 C9 H9 119.4
C9 C10 C11 120.13(15)
C9 C10 H10 119.9
C11 C10 H10 119.9
C12 C11 C10 119.59(15)
C12 C11 H11 120.2
C10 C11 H11 120.2
C11 C12 C13 120.16(15)
C11 C12 H12 119.9
C13 C12 H12 119.9
C8 C13 C12 121.06(15)
C8 C13 H13 119.5
C12 C13 H13 119.5
C7 C14 H14A 109.5
C7 C14 H14B 109.5
H14A C14 H14B 109.5
C7 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C7 C15 H15A 109.5
C7 C15 H15B 109.5
H15A C15 H15B 109.5
C7 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
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
C6 C1 C2 C3 2.0(2)
O1 C1 C2 C3 -177.87(13)
C1 C2 C3 C4 -0.9(2)
C2 C3 C4 C5 -0.6(2)
C2 C3 C4 C7 175.24(14)
C3 C4 C5 C6 1.0(2)
C7 C4 C5 C6 -174.70(15)
O1 C1 C6 C5 178.25(14)
C2 C1 C6 C5 -1.7(2)
C4 C5 C6 C1 0.1(2)
C5 C4 C7 C8 -136.75(15)
C3 C4 C7 C8 47.71(18)
C5 C4 C7 C15 100.92(17)
C3 C4 C7 C15 -74.61(17)
C5 C4 C7 C14 -17.6(2)
C3 C4 C7 C14 166.89(14)
C4 C7 C8 C13 -128.63(15)
C15 C7 C8 C13 -9.4(2)
C14 C7 C8 C13 109.18(16)
C4 C7 C8 C9 53.86(17)
C15 C7 C8 C9 173.13(14)
C14 C7 C8 C9 -68.33(17)
C13 C8 C9 C10 -1.4(2)
C7 C8 C9 C10 176.21(14)
C8 C9 C10 C11 0.3(2)
C9 C10 C11 C12 1.2(2)
C10 C11 C12 C13 -1.6(2)
C9 C8 C13 C12 1.1(2)
C7 C8 C13 C12 -176.45(14)
C11 C12 C13 C8 0.4(2)
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 O1 8_544 0.83 1.88 2.7100(10) 173 yes