#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/47/2224782.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_2224782
loop_
_publ_author_name
'Guzei, Ilia A.'
'Annamalai, Senthilvelan'
'Zimmerman, Howard E.'
_publ_section_title
;
 2-Methoxy-3,4-diphenylphenol
;
_journal_coeditor_code           TK2575
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o72
_journal_paper_doi               10.1107/S1600536809050855
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C19 H16 O2'
_chemical_formula_moiety         'C19 H16 O2'
_chemical_formula_sum            'C19 H16 O2'
_chemical_formula_weight         276.32
_chemical_name_systematic
;
2-Methoxy-3,4-diphenylphenol
;
_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
_cell_angle_alpha                90
_cell_angle_beta                 102.930(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.312(3)
_cell_length_b                   6.2585(14)
_cell_length_c                   17.167(4)
_cell_measurement_reflns_used    999
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.4
_cell_volume                     1498.7(6)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'GIS (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'local programs (Guzei, 2007) and publCIF (Westrip, 2009)'
_computing_structure_refinement
'SHELXTL (Sheldrick, 2008) and OLEX2 (Dolomanov et al.,  2009)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'doubly curved silicon crystal'
_diffrn_radiation_source         'micro-focus sealed tube'
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.040
_diffrn_reflns_av_sigmaI/netI    0.029
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13658
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.4
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2007)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.19
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.01
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2645
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.01
_refine_ls_R_factor_all          0.063
_refine_ls_R_factor_gt           0.039
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0877P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.114
_refine_ls_wR_factor_ref         0.129
_reflns_number_gt                1897
_reflns_number_total             2645
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2575.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2224782
_cod_database_fobs_code          2224782
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 0.40221(7) 0.44465(18) 0.45356(6) 0.0466(3) Uani d . 1 . .
O O2 0.55156(8) 0.1831(2) 0.44401(8) 0.0630(4) Uani d . 1 . .
H H2 0.5431 0.2608 0.4803 0.095 Uiso calc R 1 . .
C C1 0.39866(10) 0.3357(2) 0.38259(9) 0.0388(4) Uani d . 1 . .
C C2 0.47494(10) 0.2000(3) 0.38019(10) 0.0443(4) Uani d . 1 . .
C C3 0.47283(12) 0.0780(3) 0.31276(11) 0.0501(5) Uani d . 1 . .
H H3 0.5228 -0.0155 0.3110 0.060 Uiso calc R 1 . .
C C4 0.39596(11) 0.0956(3) 0.24786(10) 0.0453(4) Uani d . 1 . .
H H4 0.3945 0.0107 0.2031 0.054 Uiso calc R 1 . .
C C5 0.32054(10) 0.2373(2) 0.24768(9) 0.0388(4) Uani d . 1 . .
C C6 0.32128(10) 0.3600(2) 0.31656(9) 0.0352(4) Uani d . 1 . .
C C7 0.35107(16) 0.3378(4) 0.50515(13) 0.0751(6) Uani d . 1 . .
H H7A 0.2843 0.3301 0.4795 0.113 Uiso calc R 1 . .
H H7C 0.3586 0.4158 0.5543 0.113 Uiso calc R 1 . .
H H7B 0.3761 0.1960 0.5162 0.113 Uiso calc R 1 . .
C C8 0.24411(10) 0.2612(3) 0.17289(10) 0.0413(4) Uani d . 1 . .
C C9 0.22906(13) 0.4551(3) 0.13291(11) 0.0532(5) Uani d . 1 . .
H H9 0.2650 0.5736 0.1542 0.064 Uiso calc R 1 . .
C C10 0.16117(15) 0.4750(4) 0.06154(12) 0.0648(6) Uani d . 1 . .
H H10 0.1522 0.6063 0.0355 0.078 Uiso calc R 1 . .
C C11 0.10739(14) 0.3023(4) 0.02930(12) 0.0668(6) Uani d . 1 . .
H H11 0.0620 0.3157 -0.0185 0.080 Uiso calc R 1 . .
C C12 0.12096(13) 0.1098(4) 0.06801(13) 0.0660(6) Uani d . 1 . .
H H12 0.0843 -0.0074 0.0463 0.079 Uiso calc R 1 . .
C C13 0.18878(12) 0.0874(3) 0.13916(11) 0.0532(5) Uani d . 1 . .
H H13 0.1974 -0.0447 0.1646 0.064 Uiso calc R 1 . .
C C14 0.24119(10) 0.5068(2) 0.32365(9) 0.0368(4) Uani d . 1 . .
C C15 0.25989(12) 0.7172(3) 0.34987(10) 0.0464(4) Uani d . 1 . .
H H15 0.3223 0.7691 0.3600 0.056 Uiso calc R 1 . .
C C16 0.18630(14) 0.8488(3) 0.36086(11) 0.0580(5) Uani d . 1 . .
H H16 0.1996 0.9883 0.3785 0.070 Uiso calc R 1 . .
C C17 0.09338(14) 0.7743(3) 0.34579(12) 0.0634(5) Uani d . 1 . .
H H17 0.0441 0.8626 0.3538 0.076 Uiso calc R 1 . .
C C18 0.07375(12) 0.5682(3) 0.31880(12) 0.0577(5) Uani d . 1 . .
H H18 0.0110 0.5179 0.3081 0.069 Uiso calc R 1 . .
C C19 0.14693(11) 0.4360(3) 0.30755(10) 0.0456(4) Uani d . 1 . .
H H19 0.1328 0.2975 0.2889 0.055 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
C1 O1 C7 . . 112.95(13) ?
C2 O2 H2 . . 109.5 ?
O1 C1 C2 . . 116.83(13) ?
O1 C1 C6 . . 121.54(13) ?
C2 C1 C6 . . 121.63(14) ?
O2 C2 C3 . . 119.41(14) ?
O2 C2 C1 . . 121.10(15) ?
C3 C2 C1 . . 119.49(15) ?
C2 C3 C4 . . 119.66(15) ?
C2 C3 H3 . . 120.2 ?
C4 C3 H3 . . 120.2 ?
C3 C4 C5 . . 121.82(16) ?
C3 C4 H4 . . 119.1 ?
C5 C4 H4 . . 119.1 ?
C4 C5 C6 . . 118.94(14) ?
C4 C5 C8 . . 118.79(14) ?
C6 C5 C8 . . 122.20(13) ?
C1 C6 C5 . . 118.38(13) ?
C1 C6 C14 . . 118.76(13) ?
C5 C6 C14 . . 122.79(13) ?
O1 C7 H7A . . 109.5 ?
O1 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
O1 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
H7C C7 H7B . . 109.5 ?
C9 C8 C13 . . 117.81(16) ?
C9 C8 C5 . . 120.99(15) ?
C13 C8 C5 . . 121.14(15) ?
C8 C9 C10 . . 121.06(18) ?
C8 C9 H9 . . 119.5 ?
C10 C9 H9 . . 119.5 ?
C11 C10 C9 . . 120.29(19) ?
C11 C10 H10 . . 119.9 ?
C9 C10 H10 . . 119.9 ?
C12 C11 C10 . . 119.52(18) ?
C12 C11 H11 . . 120.2 ?
C10 C11 H11 . . 120.2 ?
C11 C12 C13 . . 120.80(19) ?
C11 C12 H12 . . 119.6 ?
C13 C12 H12 . . 119.6 ?
C12 C13 C8 . . 120.53(17) ?
C12 C13 H13 . . 119.7 ?
C8 C13 H13 . . 119.7 ?
C19 C14 C15 . . 118.20(14) ?
C19 C14 C6 . . 121.10(14) ?
C15 C14 C6 . . 120.66(13) ?
C16 C15 C14 . . 120.53(16) ?
C16 C15 H15 . . 119.7 ?
C14 C15 H15 . . 119.7 ?
C17 C16 C15 . . 120.36(17) ?
C17 C16 H16 . . 119.8 ?
C15 C16 H16 . . 119.8 ?
C18 C17 C16 . . 119.70(16) ?
C18 C17 H17 . . 120.2 ?
C16 C17 H17 . . 120.2 ?
C17 C18 C19 . . 120.23(17) ?
C17 C18 H18 . . 119.9 ?
C19 C18 H18 . . 119.9 ?
C18 C19 C14 . . 120.97(16) ?
C18 C19 H19 . . 119.5 ?
C14 C19 H19 . . 119.5 ?
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 C1 . 1.3871(18) ?
O1 C7 . 1.434(2) ?
O2 C2 . 1.3698(19) ?
O2 H2 . 0.8200 ?
C1 C2 . 1.391(2) ?
C1 C6 . 1.405(2) ?
C2 C3 . 1.382(2) ?
C3 C4 . 1.384(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.397(2) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.408(2) ?
C5 C8 . 1.496(2) ?
C6 C14 . 1.495(2) ?
C7 H7A . 0.9600 ?
C7 H7C . 0.9600 ?
C7 H7B . 0.9600 ?
C8 C9 . 1.387(2) ?
C8 C13 . 1.393(2) ?
C9 C10 . 1.389(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.370(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.368(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.387(3) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C14 C19 . 1.388(2) ?
C14 C15 . 1.398(2) ?
C15 C16 . 1.383(2) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.378(3) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.378(3) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.382(2) ?
C18 H18 . 0.9300 ?
C19 H19 . 0.9300 ?
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
O2 H2 O1 3_666 0.82 2.21 2.9043(18) 142
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
C7 O1 C1 C2 . . . . -94.89(18) ?
C7 O1 C1 C6 . . . . 84.55(18) ?
O1 C1 C2 O2 . . . . -2.8(2) ?
C6 C1 C2 O2 . . . . 177.77(14) ?
O1 C1 C2 C3 . . . . 176.31(14) ?
C6 C1 C2 C3 . . . . -3.1(2) ?
O2 C2 C3 C4 . . . . -179.50(15) ?
C1 C2 C3 C4 . . . . 1.4(2) ?
C2 C3 C4 C5 . . . . 1.3(3) ?
C3 C4 C5 C6 . . . . -2.3(2) ?
C3 C4 C5 C8 . . . . 174.84(15) ?
O1 C1 C6 C5 . . . . -177.28(13) ?
C2 C1 C6 C5 . . . . 2.1(2) ?
O1 C1 C6 C14 . . . . -0.1(2) ?
C2 C1 C6 C14 . . . . 179.32(14) ?
C4 C5 C6 C1 . . . . 0.6(2) ?
C8 C5 C6 C1 . . . . -176.46(13) ?
C4 C5 C6 C14 . . . . -176.52(13) ?
C8 C5 C6 C14 . . . . 6.5(2) ?
C4 C5 C8 C9 . . . . -117.18(18) ?
C6 C5 C8 C9 . . . . 59.8(2) ?
C4 C5 C8 C13 . . . . 59.8(2) ?
C6 C5 C8 C13 . . . . -123.15(17) ?
C13 C8 C9 C10 . . . . -0.1(3) ?
C5 C8 C9 C10 . . . . 177.00(16) ?
C8 C9 C10 C11 . . . . 0.1(3) ?
C9 C10 C11 C12 . . . . 0.1(3) ?
C10 C11 C12 C13 . . . . -0.3(3) ?
C11 C12 C13 C8 . . . . 0.4(3) ?
C9 C8 C13 C12 . . . . -0.2(2) ?
C5 C8 C13 C12 . . . . -177.25(16) ?
C1 C6 C14 C19 . . . . -125.28(16) ?
C5 C6 C14 C19 . . . . 51.8(2) ?
C1 C6 C14 C15 . . . . 52.1(2) ?
C5 C6 C14 C15 . . . . -130.82(16) ?
C19 C14 C15 C16 . . . . 1.3(2) ?
C6 C14 C15 C16 . . . . -176.18(15) ?
C14 C15 C16 C17 . . . . -0.2(3) ?
C15 C16 C17 C18 . . . . -0.7(3) ?
C16 C17 C18 C19 . . . . 0.6(3) ?
C17 C18 C19 C14 . . . . 0.5(3) ?
C15 C14 C19 C18 . . . . -1.4(2) ?
C6 C14 C19 C18 . . . . 176.05(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743995
