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###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
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#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
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data_general
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-07-21
_journal_date_accepted     2010-07-23
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      8
_journal_page_first     o2136
_journal_page_last     o2136
_journal_paper_category     QO
_journal_coeditor_code     HB5570
_publ_contact_author_name     ' Edward RT Tiekink '
_publ_contact_author_address
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
_publ_contact_author_email
;
Edward.Tiekink@gmail.com
;
_publ_contact_author_fax     ' +60 3 7967 4193 '
_publ_contact_author_phone     ' +60 3 7967 6775 '
_publ_section_title
;
(2-Methylphenyl)(phenyl)methanol
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    ' Siddaraju, B. P. ' .
;
Department of Chemistry, V. V. Puram College of Science,
Bangalore 560 004, India
;
    ' Yathirajan, H. S. '
;
Additional correspondence author, e-mail: yathirajan@hotmail.com.
;
;
Department of Studies in Chemistry, University of Mysore, Manasagangotri,
Mysore 570 006, India
;
    ' Narayana, B. ' .
;
Department of Studies in Chemistry, Mangalore University, Mangalagangotri
574 199, India
;
    'Ng, Seik Weng' .
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
    'Tiekink, Edward R. T.' .
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
_publ_section_synopsis     .
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(2-Methylphenyl)(phenyl)methanol
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H14 O'
_chemical_formula_sum     'C14 H14 O'
_chemical_formula_iupac     'C14 H14 O'
_chemical_formula_weight     198.25
_chemical_melting_point     ?
_symmetry_cell_setting     trigonal
_symmetry_space_group_name_H-M     'R -3'
_symmetry_space_group_name_Hall     '-R 3'
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'
_cell_length_a     23.013(2)
_cell_length_b     23.013
_cell_length_c     10.6067(11)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     120
_cell_volume     4864.8(7)
_cell_formula_units_Z     18
_cell_measurement_reflns_used     2551
_cell_measurement_theta_min     2.8
_cell_measurement_theta_max     28.3
_cell_measurement_temperature     100(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.35
_exptl_crystal_size_min     0.30
_exptl_crystal_density_diffrn     1.218
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1908
_exptl_absorpt_coefficient_mu     0.075
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.971
_exptl_absorpt_correction_T_max     0.978
_exptl_special_details
;
;
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX CCD'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6286
_diffrn_reflns_av_R_equivalents     0.026
_diffrn_reflns_av_sigmaI/netI     0.034
_diffrn_reflns_theta_min     1.8
_diffrn_reflns_theta_max     27.5
_diffrn_reflns_theta_full     27.5
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -28
_diffrn_reflns_limit_h_max     28
_diffrn_reflns_limit_k_min     -29
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     2475
_reflns_number_gt     2022
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.057
_refine_ls_R_factor_gt     0.045
_refine_ls_wR_factor_gt     0.115
_refine_ls_wR_factor_ref     0.121
_refine_ls_goodness_of_fit_ref     1.08
_refine_ls_restrained_S_all     1.08
_refine_ls_number_reflns     2475
_refine_ls_number_parameters     141
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0533P)²+4.2609P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     ?
_refine_ls_shift/su_max_lt     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.43
_refine_diff_density_min     -0.30
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'APEX2 (Bruker, 2008)'
_computing_cell_refinement     'SAINT (Bruker, 2008)'
_computing_data_reduction     'SAINT (Bruker, 2008)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)
;
_computing_publication_material     'publCIF (Westrip, 2010)'
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 0.13170(5) 0.08915(5) 0.01453(9) 0.0229(2) Uani d D 1 . .
    H H1 0.1201(9) 0.0483(5) 0.0010(18) 0.043(5) Uiso d D 1 . .
    C C1 0.20865(7) 0.19098(7) 0.11187(14) 0.0237(3) Uani d . 1 . .
    C C2 0.18864(8) 0.21209(7) 0.21715(15) 0.0306(3) Uani d . 1 . .
    H H2 0.1637 0.1808 0.2816 0.037 Uiso calc R 1 . .
    C C3 0.20471(9) 0.27864(8) 0.22928(18) 0.0417(4) Uani d . 1 . .
    H H3 0.1911 0.2930 0.3018 0.050 Uiso calc R 1 . .
    C C4 0.24081(9) 0.32372(8) 0.1346(2) 0.0495(5) Uani d . 1 . .
    H H4 0.2523 0.3694 0.1423 0.059 Uiso calc R 1 . .
    C C5 0.26018(8) 0.30288(8) 0.0295(2) 0.0433(5) Uani d . 1 . .
    H H5 0.2847 0.3344 -0.0349 0.052 Uiso calc R 1 . .
    C C6 0.24463(7) 0.23669(7) 0.01529(16) 0.0321(4) Uani d . 1 . .
    C C7 0.26458(8) 0.21578(9) -0.10289(17) 0.0422(4) Uani d . 1 . .
    H H7A 0.2878 0.2545 -0.1591 0.063 Uiso calc R 1 . .
    H H7B 0.2244 0.1806 -0.1450 0.063 Uiso calc R 1 . .
    H H7C 0.2946 0.1984 -0.0819 0.063 Uiso calc R 1 . .
    C C8 0.18897(6) 0.11780(6) 0.09612(12) 0.0206(3) Uani d . 1 . .
    H H8 0.2264 0.1162 0.0515 0.025 Uiso calc R 1 . .
    C C9 0.17524(6) 0.07865(6) 0.21775(12) 0.0183(3) Uani d . 1 . .
    C C10 0.22851(7) 0.08429(7) 0.28925(13) 0.0247(3) Uani d . 1 . .
    H H10 0.2733 0.1148 0.2642 0.030 Uiso calc R 1 . .
    C C11 0.21660(7) 0.04561(7) 0.39708(14) 0.0276(3) Uani d . 1 . .
    H H11 0.2533 0.0500 0.4457 0.033 Uiso calc R 1 . .
    C C12 0.15144(7) 0.00071(7) 0.43395(13) 0.0247(3) Uani d . 1 . .
    H H12 0.1433 -0.0263 0.5069 0.030 Uiso calc R 1 . .
    C C13 0.09838(7) -0.00461(7) 0.36404(13) 0.0229(3) Uani d . 1 . .
    H H13 0.0536 -0.0350 0.3894 0.027 Uiso calc R 1 . .
    C C14 0.11032(7) 0.03426(6) 0.25682(13) 0.0207(3) Uani d . 1 . .
    H H14 0.0735 0.0304 0.2095 0.025 Uiso calc R 1 . .
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 0.0260(5) 0.0200(5) 0.0247(5) 0.0130(4) -0.0060(4) -0.0017(4)
    C1 0.0180(6) 0.0186(6) 0.0340(8) 0.0087(5) -0.0060(5) 0.0017(5)
    C2 0.0317(8) 0.0235(7) 0.0397(9) 0.0161(6) -0.0096(6) -0.0041(6)
    C3 0.0449(10) 0.0297(8) 0.0577(11) 0.0241(8) -0.0221(8) -0.0149(8)
    C4 0.0386(10) 0.0164(7) 0.0895(15) 0.0106(7) -0.0297(10) -0.0038(8)
    C5 0.0261(8) 0.0226(8) 0.0717(13) 0.0051(6) -0.0108(8) 0.0127(8)
    C6 0.0162(6) 0.0257(7) 0.0487(10) 0.0062(6) -0.0050(6) 0.0106(7)
    C7 0.0275(8) 0.0477(10) 0.0491(10) 0.0171(8) 0.0090(7) 0.0230(8)
    C8 0.0190(6) 0.0213(6) 0.0239(7) 0.0118(5) -0.0006(5) 0.0022(5)
    C9 0.0205(6) 0.0158(6) 0.0209(6) 0.0107(5) -0.0001(5) -0.0007(5)
    C10 0.0188(6) 0.0233(7) 0.0301(7) 0.0091(5) -0.0017(5) 0.0023(5)
    C11 0.0246(7) 0.0302(8) 0.0289(8) 0.0144(6) -0.0055(6) 0.0027(6)
    C12 0.0301(7) 0.0228(7) 0.0234(7) 0.0148(6) -0.0001(5) 0.0027(5)
    C13 0.0220(7) 0.0217(6) 0.0237(7) 0.0100(5) 0.0020(5) -0.0008(5)
    C14 0.0193(6) 0.0218(6) 0.0230(7) 0.0118(5) -0.0014(5) -0.0016(5)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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 C8 . 1.4323(16) ?
    O1 H1 . 0.852(9) ?
    C1 C2 . 1.385(2) ?
    C1 C6 . 1.404(2) ?
    C1 C8 . 1.5188(18) ?
    C2 C3 . 1.390(2) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.383(3) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.373(3) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.388(2) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.495(3) ?
    C7 H7A . 0.9800 ?
    C7 H7B . 0.9800 ?
    C7 H7C . 0.9800 ?
    C8 C9 . 1.5137(18) ?
    C8 H8 . 1.0000 ?
    C9 C14 . 1.3862(18) ?
    C9 C10 . 1.3911(18) ?
    C10 C11 . 1.390(2) ?
    C10 H10 . 0.9500 ?
    C11 C12 . 1.386(2) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.3806(19) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.3868(19) ?
    C13 H13 . 0.9500 ?
    C14 H14 . 0.9500 ?
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
    C8 O1 H1 . . 108.5(13) ?
    C2 C1 C6 . . 120.03(13) ?
    C2 C1 C8 . . 120.69(13) ?
    C6 C1 C8 . . 119.20(13) ?
    C1 C2 C3 . . 120.59(16) ?
    C1 C2 H2 . . 119.7 ?
    C3 C2 H2 . . 119.7 ?
    C4 C3 C2 . . 119.23(18) ?
    C4 C3 H3 . . 120.4 ?
    C2 C3 H3 . . 120.4 ?
    C5 C4 C3 . . 120.38(15) ?
    C5 C4 H4 . . 119.8 ?
    C3 C4 H4 . . 119.8 ?
    C4 C5 C6 . . 121.39(17) ?
    C4 C5 H5 . . 119.3 ?
    C6 C5 H5 . . 119.3 ?
    C5 C6 C1 . . 118.37(16) ?
    C5 C6 C7 . . 119.48(15) ?
    C1 C6 C7 . . 122.12(14) ?
    C6 C7 H7A . . 109.5 ?
    C6 C7 H7B . . 109.5 ?
    H7A C7 H7B . . 109.5 ?
    C6 C7 H7C . . 109.5 ?
    H7A C7 H7C . . 109.5 ?
    H7B C7 H7C . . 109.5 ?
    O1 C8 C9 . . 111.77(10) ?
    O1 C8 C1 . . 105.81(10) ?
    C9 C8 C1 . . 115.10(11) ?
    O1 C8 H8 . . 108.0 ?
    C9 C8 H8 . . 108.0 ?
    C1 C8 H8 . . 108.0 ?
    C14 C9 C10 . . 118.73(12) ?
    C14 C9 C8 . . 121.37(12) ?
    C10 C9 C8 . . 119.81(11) ?
    C11 C10 C9 . . 120.43(13) ?
    C11 C10 H10 . . 119.8 ?
    C9 C10 H10 . . 119.8 ?
    C12 C11 C10 . . 120.20(13) ?
    C12 C11 H11 . . 119.9 ?
    C10 C11 H11 . . 119.9 ?
    C13 C12 C11 . . 119.60(13) ?
    C13 C12 H12 . . 120.2 ?
    C11 C12 H12 . . 120.2 ?
    C12 C13 C14 . . 120.14(13) ?
    C12 C13 H13 . . 119.9 ?
    C14 C13 H13 . . 119.9 ?
    C9 C14 C13 . . 120.89(12) ?
    C9 C14 H14 . . 119.6 ?
    C13 C14 H14 . . 119.6 ?
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 . . . . -1.0(2) ?
    C8 C1 C2 C3 . . . . -177.73(13) ?
    C1 C2 C3 C4 . . . . 0.3(2) ?
    C2 C3 C4 C5 . . . . 0.4(2) ?
    C3 C4 C5 C6 . . . . -0.3(2) ?
    C4 C5 C6 C1 . . . . -0.4(2) ?
    C4 C5 C6 C7 . . . . 177.76(15) ?
    C2 C1 C6 C5 . . . . 1.0(2) ?
    C8 C1 C6 C5 . . . . 177.84(13) ?
    C2 C1 C6 C7 . . . . -177.07(14) ?
    C8 C1 C6 C7 . . . . -0.3(2) ?
    C2 C1 C8 O1 . . . . 98.25(14) ?
    C6 C1 C8 O1 . . . . -78.54(14) ?
    C2 C1 C8 C9 . . . . -25.70(17) ?
    C6 C1 C8 C9 . . . . 157.52(12) ?
    O1 C8 C9 C14 . . . . -17.47(17) ?
    C1 C8 C9 C14 . . . . 103.27(14) ?
    O1 C8 C9 C10 . . . . 159.14(12) ?
    C1 C8 C9 C10 . . . . -80.12(15) ?
    C14 C9 C10 C11 . . . . 0.6(2) ?
    C8 C9 C10 C11 . . . . -176.11(12) ?
    C9 C10 C11 C12 . . . . 0.4(2) ?
    C10 C11 C12 C13 . . . . -1.0(2) ?
    C11 C12 C13 C14 . . . . 0.7(2) ?
    C10 C9 C14 C13 . . . . -0.92(19) ?
    C8 C9 C14 C13 . . . . 175.72(12) ?
    C12 C13 C14 C9 . . . . 0.3(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
    O1 H1 O1 11 0.852(9) 1.848(9) 2.6967(10) 174.1(19)
