#------------------------------------------------------------------------------
#$Date: 2016-02-25 04:34:29 +0200 (Thu, 25 Feb 2016) $
#$Revision: 176881 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/15/2241585.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_2241585
loop_
_publ_author_name
'Harrison, William T. A.'
'Plater, M. John'
'Yin, Lee J.'
_publ_section_title
;
 Investigations of new potential photo-acid generators: crystal structures
 of 2-[(E)-2-phenylethenyl]phenol (orthorhombic polymorph) and
 (2E)-3-(2-bromophenyl)-2-phenylprop-2-enoic acid
;
_journal_coeditor_code           SU5278
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              407
_journal_page_last               411
_journal_paper_doi               10.1107/S2056989016002942
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C14 H12 O'
_chemical_formula_moiety         'C14 H12 O'
_chemical_formula_sum            'C14 H12 O'
_chemical_formula_weight         196.24
_chemical_name_systematic
;
2-[(E)-2-Phenylethenyl]phenol
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6193(8)
_cell_length_b                   7.6800(5)
_cell_length_c                   11.3584(8)
_cell_measurement_reflns_used    7085
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.5
_cell_volume                     1013.58(12)
_computing_cell_refinement
;
CrystalClear (Rigaku, 2010)
;
_computing_data_collection
;
CrystalClear (Rigaku, 2010)
;
_computing_data_reduction
;
CrystalClear (Rigaku, 2010)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and ATOMS (Dowty, 1999)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6984
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.65
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       slab
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.147
_refine_ls_abs_structure_details none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2271
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0341
_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)+(0.0581P)²+0.0566P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0913
_reflns_number_gt                2132
_reflns_number_total             2271
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su5278sup1.cif
_cod_data_source_block           I
_cod_database_code               2241585
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.30887(12) 0.13815(16) 0.08810(11) 0.0230(3) Uani d . 1 1 . .
H H1 0.3652 0.0929 0.0386 0.028 Uiso d PR 0.205(3) 1 A 2
C C2 0.19331(12) 0.12759(16) 0.05641(11) 0.0258(3) Uani d . 1 1 A .
H H2 0.1721 0.0723 -0.0152 0.031 Uiso calc R 1 1 . .
C C3 0.10941(12) 0.19707(16) 0.12852(12) 0.0249(3) Uani d . 1 1 . .
H H3 0.0307 0.1890 0.1067 0.030 Uiso calc R 1 1 A .
C C4 0.14037(12) 0.27928(17) 0.23349(12) 0.0244(3) Uani d . 1 1 A .
H H4 0.0829 0.3280 0.2831 0.029 Uiso calc R 1 1 . .
C C5 0.25559(12) 0.28929(14) 0.26490(11) 0.0222(3) Uani d . 1 1 . .
H H5 0.2759 0.3456 0.3364 0.027 Uiso calc R 1 1 A .
C C6 0.34307(12) 0.21877(16) 0.19426(10) 0.0207(3) Uani d . 1 1 A .
C C7 0.46529(12) 0.22186(16) 0.22775(11) 0.0210(3) Uani d . 1 1 . .
H H7 0.5184 0.1701 0.1746 0.025 Uiso calc R 1 1 A .
C C8 0.50832(12) 0.29131(15) 0.32669(11) 0.0219(3) Uani d . 1 1 A .
H H8 0.4550 0.3453 0.3786 0.026 Uiso calc R 1 1 . .
C C9 0.62995(11) 0.29221(15) 0.36292(11) 0.0203(3) Uani d . 1 1 . .
C C10 0.71722(12) 0.21042(16) 0.29798(11) 0.0229(3) Uani d . 1 1 A .
H H10 0.6982 0.1498 0.2277 0.027 Uiso calc R 1 1 . .
C C11 0.83100(13) 0.21675(16) 0.33495(12) 0.0259(3) Uani d . 1 1 . .
H H11 0.8892 0.1621 0.2893 0.031 Uiso calc R 1 1 A .
C C12 0.86041(12) 0.30333(17) 0.43927(13) 0.0273(3) Uani d . 1 1 A .
H H12 0.9383 0.3073 0.4646 0.033 Uiso calc R 1 1 . .
C C13 0.77504(12) 0.38320(16) 0.50516(11) 0.0265(3) Uani d . 1 1 . .
H H13 0.7943 0.4413 0.5763 0.032 Uiso calc R 1 1 A .
C C14 0.66125(13) 0.37858(16) 0.46739(11) 0.0241(3) Uani d . 1 1 A .
H H14 0.6045 0.4340 0.5121 0.029 Uiso d PR 0.795(3) 1 A 1
O O1 0.39106(10) 0.07105(15) 0.01715(10) 0.0261(3) Uani d P 0.795(3) 1 A 1
H H1O 0.3492 0.0078 -0.0443 0.031 Uiso d PR 0.795(3) 1 A 1
O O2 0.5932(4) 0.4523(7) 0.5351(5) 0.0305(15) Uani d P 0.205(3) 1 A 2
H H2O 0.6381 0.5365 0.5670 0.037 Uiso d PR 0.205(3) 1 A 2
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
O1 C1 C2 120.33(12)
O1 C1 C6 118.51(12)
C2 C1 C6 121.17(12)
O1 C1 H1 0.7
C2 C1 H1 120.0
C6 C1 H1 118.8
C3 C2 C1 120.33(11)
C3 C2 H2 119.8
C1 C2 H2 119.8
C2 C3 C4 119.97(13)
C2 C3 H3 120.0
C4 C3 H3 120.0
C5 C4 C3 119.55(13)
C5 C4 H4 120.2
C3 C4 H4 120.2
C4 C5 C6 122.03(12)
C4 C5 H5 119.0
C6 C5 H5 119.0
C5 C6 C1 116.96(12)
C5 C6 C7 123.05(11)
C1 C6 C7 119.98(11)
C8 C7 C6 125.69(12)
C8 C7 H7 117.2
C6 C7 H7 117.2
C7 C8 C9 126.46(12)
C7 C8 H8 116.8
C9 C8 H8 116.8
C10 C9 C14 117.89(12)
C10 C9 C8 123.03(11)
C14 C9 C8 119.08(12)
C11 C10 C9 120.92(12)
C11 C10 H10 119.5
C9 C10 H10 119.5
C10 C11 C12 120.32(13)
C10 C11 H11 119.8
C12 C11 H11 119.8
C13 C12 C11 119.49(13)
C13 C12 H12 120.3
C11 C12 H12 120.3
C12 C13 C14 120.18(12)
C12 C13 H13 119.9
C14 C13 H13 119.9
O2 C14 C13 113.8(3)
O2 C14 C9 125.0(3)
C13 C14 C9 121.19(13)
C13 C14 H14 119.4
C9 C14 H14 119.4
C1 O1 H1O 105.2
C14 O2 H2O 101.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.3517(17)
C1 C2 1.3925(18)
C1 C6 1.4126(18)
C1 H1 0.9300
C2 C3 1.381(2)
C2 H2 0.9500
C3 C4 1.3963(19)
C3 H3 0.9500
C4 C5 1.388(2)
C4 H4 0.9500
C5 C6 1.4036(18)
C5 H5 0.9500
C6 C7 1.4703(19)
C7 C8 1.3407(16)
C7 H7 0.9500
C8 C9 1.4720(18)
C8 H8 0.9500
C9 C10 1.4024(17)
C9 C14 1.4073(18)
C10 C11 1.388(2)
C10 H10 0.9500
C11 C12 1.401(2)
C11 H11 0.9500
C12 C13 1.386(2)
C12 H12 0.9500
C13 C14 1.390(2)
C13 H13 0.9500
C14 O2 1.240(5)
C14 H14 0.9340
O1 H1O 0.9794
O2 H2O 0.9057
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 H1o Cg2 2_654 0.98 2.66 3.5028(13) 144
O2 H2o Cg1 1_555 0.91 2.74 3.646(2) 179
C5 H5 Cg2 4_465 0.95 2.86 3.5337(12) 129
C10 H10 Cg1 4_555 0.95 2.87 3.5742(14) 132
C13 H13 Cg1 2_665 0.95 2.87 3.6015(14) 135
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
O1 C1 C2 C3 -179.60(12)
C6 C1 C2 C3 0.32(18)
C1 C2 C3 C4 0.36(19)
C2 C3 C4 C5 -0.47(19)
C3 C4 C5 C6 -0.10(19)
C4 C5 C6 C1 0.74(17)
C4 C5 C6 C7 -177.62(12)
O1 C1 C6 C5 179.07(11)
C2 C1 C6 C5 -0.85(17)
O1 C1 C6 C7 -2.52(17)
C2 C1 C6 C7 177.56(11)
C5 C6 C7 C8 -0.48(19)
C1 C6 C7 C8 -178.79(11)
C6 C7 C8 C9 178.55(12)
C7 C8 C9 C10 -3.09(18)
C7 C8 C9 C14 176.96(11)
C14 C9 C10 C11 -0.88(17)
C8 C9 C10 C11 179.16(12)
C9 C10 C11 C12 0.94(19)
C10 C11 C12 C13 -0.22(19)
C11 C12 C13 C14 -0.54(19)
C12 C13 C14 O2 178.9(3)
C12 C13 C14 C9 0.59(19)
C10 C9 C14 O2 -178.0(3)
C8 C9 C14 O2 2.0(4)
C10 C9 C14 C13 0.12(18)
C8 C9 C14 C13 -179.92(11)
