#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/24/2102480.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_2102480
loop_
_publ_author_name
'Parkin, Sean'
'Hao, Xiang'
'Brock, Carolyn Pratt'
_publ_section_title
;
 2-Biphenylol revisited
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              197
_journal_page_last               203
_journal_paper_doi               10.1107/S0108768104003696
_journal_volume                  60
_journal_year                    2004
_chemical_formula_sum            'C12 H10 O'
_chemical_formula_weight         170.20
_chemical_name_common            2-biphenylol
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_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            8
_cell_length_a                   12.871(3)
_cell_length_b                   23.939(5)
_cell_length_c                   5.8870(12)
_cell_measurement_reflns_used    605
_cell_measurement_temperature    305(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1813.9(7)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material
;
SHELX97-2 (Sheldrick, 1997) and local procedures
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      305(2)
_diffrn_detector_area_resol_mean 18
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'ω scans at fixed χ = 55°'
_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  0.0500
_diffrn_reflns_av_sigmaI/netI    0.0526
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            1005
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.40
_diffrn_standards_decay_%        <1
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9846
_exptl_absorpt_correction_T_min  0.9695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.121
_refine_diff_density_min         -0.123
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   4(4)
_refine_ls_extinction_coef       0.011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     90
_refine_ls_number_reflns         1005
_refine_ls_number_restraints     57
_refine_ls_restrained_S_all      0.942
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0740P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1331
_reflns_number_gt                557
_reflns_number_total             1005
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            bs5004.cif
_cod_data_source_block           k03123
_cod_original_cell_volume        1813.9(6)
_cod_original_sg_symbol_H-M      Fdd2
_cod_database_code               2102480
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+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_disorder_group
_atom_site_type_symbol
C1 0.0477(9) 0.0182(6) 0.5298(14) 0.0546(7) Uani d PDU 0.797(9) 1 C
C2 0.0660(10) 0.0566(4) 0.7045(9) 0.0628(17) Uani d PDU 0.797(9) 1 C
C3 0.1531(10) 0.0900(4) 0.7001(11) 0.0750(17) Uani d PDU 0.797(9) 1 C
H3 0.1649 0.1151 0.8177 0.090 Uiso calc PR 0.797(9) 1 H
C4 0.2226(11) 0.0866(7) 0.524(2) 0.0799(15) Uani d PDU 0.797(9) 1 C
H4 0.2805 0.1098 0.5220 0.096 Uiso calc PR 0.797(9) 1 H
C5 0.2066(6) 0.0489(3) 0.3519(14) 0.0738(16) Uani d PDU 0.797(9) 1 C
H5 0.2546 0.0459 0.2345 0.089 Uiso calc PR 0.797(9) 1 H
C6 0.1190(7) 0.0155(4) 0.3531(12) 0.0631(16) Uani d PDU 0.797(9) 1 C
H6 0.1077 -0.0093 0.2337 0.076 Uiso calc PR 0.797(9) 1 H
O2 -0.0045(3) 0.06093(17) 0.8734(8) 0.0760(16) Uani d PDU 0.398(4) 1 O
H2 -0.0021 0.0924 0.9278 0.091 Uiso calc PR 0.398(4) 1 H
C1' 0.042(4) 0.017(2) 0.544(8) 0.0546(7) Uani d PDU 0.203(9) 2 C
C2' 0.107(3) 0.0217(19) 0.356(8) 0.0631(16) Uani d PDU 0.203(9) 2 C
C3' 0.192(3) 0.0570(15) 0.361(8) 0.0738(16) Uani d PDU 0.203(9) 2 C
H3' 0.2351 0.0599 0.2337 0.089 Uiso calc PR 0.203(9) 2 H
C4' 0.215(4) 0.088(3) 0.552(9) 0.0799(15) Uani d PDU 0.203(9) 2 C
H4' 0.2726 0.1108 0.5546 0.096 Uiso calc PR 0.203(9) 2 H
C5' 0.151(4) 0.084(2) 0.738(7) 0.0750(17) Uani d PDU 0.203(9) 2 C
H5' 0.1650 0.1057 0.8666 0.090 Uiso calc PR 0.203(9) 2 H
C6' 0.066(4) 0.049(2) 0.736(7) 0.0628(17) Uani d PDU 0.203(9) 2 C
H6' 0.0238 0.0465 0.8644 0.075 Uiso calc PR 0.203(9) 2 H
O2' 0.1016(11) -0.0178(6) 0.191(3) 0.058(5) Uiso d PDU 0.102(4) 2 O
H2' 0.1229 -0.0477 0.2419 0.088 Uiso calc PR 0.102(4) 2 H
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
C6 C1 C2 . . 118.1(3)
C6 C1 C1 . 2 120.8(8)
C2 C1 C1 . 2 121.2(8)
O2 C2 C3 . . 121.1(7)
O2 C2 C1 . . 118.6(7)
C3 C2 C1 . . 120.3(4)
C4 C3 C2 . . 120.7(4)
C4 C3 H3 . . 119.6
C2 C3 H3 . . 119.6
C3 C4 C5 . . 120.0(3)
C3 C4 H4 . . 120.0
C5 C4 H4 . . 120.0
C4 C5 C6 . . 119.9(4)
C4 C5 H5 . . 120.0
C6 C5 H5 . . 120.0
C5 C6 C1 . . 121.0(4)
C5 C6 H6 . . 119.5
C1 C6 H6 . . 119.5
C1' C1' C2' 2 . 121(2)
C1' C1' C6' 2 . 120(2)
C2' C1' C6' . . 118.4(10)
O2' C2' C1' . . 119.3(18)
O2' C2' C3' . . 118.4(19)
C1' C2' C3' . . 120.3(11)
C4' C3' C2' . . 120.4(12)
C4' C3' H3' . . 119.8
C2' C3' H3' . . 119.8
C3' C4' C5' . . 120.0(10)
C3' C4' H4' . . 120.0
C5' C4' H4' . . 120.0
C4' C5' C6' . . 120.1(12)
C4' C5' H5' . . 119.9
C6' C5' H5' . . 119.9
C5' C6' C1' . . 120.8(13)
C5' C6' H6' . . 119.6
C1' C6' H6' . . 119.6
C2' O2' H2' . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C6 . 1.389(6)
C1 C2 . 1.399(6)
C1 C1 2 1.507(15)
C2 O2 . 1.351(9)
C2 C3 . 1.377(6)
C3 C4 . 1.369(7)
C3 H3 . 0.9300
C4 C5 . 1.374(6)
C4 H4 . 0.9300
C5 C6 . 1.383(6)
C5 H5 . 0.9300
C6 H6 . 0.9300
O2 H2 . 0.8200
C1' C1' 2 1.37(6)
C1' C2' . 1.387(17)
C1' C6' . 1.396(17)
C2' O2' . 1.357(18)
C2' C3' . 1.391(16)
C3' C4' . 1.372(16)
C3' H3' . 0.9300
C4' C5' . 1.374(16)
C4' H4' . 0.9300
C5' C6' . 1.381(16)
C5' H5' . 0.9300
C6' H6' . 0.9300
O2' H2' . 0.8200
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
C6 C1 C2 O2 . 177.9(10)
C1 C1 C2 O2 2 -0.8(18)
C6 C1 C2 C3 . -0.6(10)
C1 C1 C2 C3 2 -179.2(18)
O2 C2 C3 C4 . -177.9(12)
C1 C2 C3 C4 . 0.5(13)
C2 C3 C4 C5 . -1.1(17)
C3 C4 C5 C6 . 1.6(15)
C4 C5 C6 C1 . -1.7(8)
C2 C1 C6 C5 . 1.2(7)
C1 C1 C6 C5 2 179.8(19)
C1' C1' C2' O2' 2 -16(7)
C6' C1' C2' O2' . 164(5)
C1' C1' C2' C3' 2 -179(9)
C6' C1' C2' C3' . 0(2)
O2' C2' C3' C4' . -164(6)
C1' C2' C3' C4' . 0(3)
C2' C3' C4' C5' . -1(6)
C3' C4' C5' C6' . 1(7)
C4' C5' C6' C1' . -1(6)
C1' C1' C6' C5' 2 180(8)
C2' C1' C6' C5' . 1(4)
