#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/42/4024208.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_4024208
loop_
_publ_author_name
'Daniele Casarini'
'Lodovico Lunazzi'
'Michele Mancinelli'
'Andrea Mazzanti'
'Carlo Rosini'
_publ_contact_author
;
Dr. Andrea Mazzanti
University of Bologna
Department of Organic Chemistry A.Mangini
Viale Risorgimento 4
40136 Bologna
Italy
;
_publ_contact_author_email       mazzand@ms.fci.unibo.it
_publ_contact_author_fax         '[039]051 209 3654'
_publ_contact_author_phone       '[039]051 209 3633'
_publ_section_title
;
 Structure, Conformation, Stereodynamics, Dimer Formation, and
 Absolute Configuration of Axially Chiral Atropisomers of
 Hindered Biphenyl Carbinols
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7667
_journal_page_last               7676
_journal_paper_doi               10.1021/jo701481m
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C18 H22 O2'
_chemical_formula_sum            'C18 H22 O2'
_chemical_formula_weight         270.36
_chemical_name_systematic
; 
 2,2'-(biphenyl-2,2'-diyl)dipropan-2-ol  
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             30/03/2007
_audit_creation_method           SHELXL-97
_audit_update_record             30/06/2007
_cell_angle_alpha                118.0260(10)
_cell_angle_beta                 95.944(2)
_cell_angle_gamma                101.472(2)
_cell_formula_units_Z            2
_cell_length_a                   8.9963(13)
_cell_length_b                   9.9418(14)
_cell_length_c                   10.2139(14)
_cell_measurement_reflns_used    357
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.55
_cell_measurement_theta_min      2.32
_cell_volume                     769.52(19)
_computing_cell_refinement       'Bruker APEX 2 V1.0-27'
_computing_data_collection       'Bruker APEX 2 V1.0-27'
_computing_data_reduction        'Bruker APEX 2 V1.0-27'
_computing_molecular_graphics    'mercury 1.4.1'
_computing_publication_material  'mercury 1.4.1'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX 2'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0156
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7332
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.9926
_exptl_absorpt_correction_T_min  0.9709
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       brick
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2701
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0413
_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)+(0.0719P)²+0.1103P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1316
_reflns_number_gt                2296
_reflns_number_total             2701
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo701481m_data1_0824.cif
_cod_data_source_block           p-1
_cod_database_code               4024208
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.15382(16) 0.95565(16) 0.19557(15) 0.0396(3) Uani 1 1 d . . .
C2 C 0.23283(16) 1.11378(16) 0.24639(15) 0.0402(3) Uani 1 1 d . . .
C3 C 0.1751(2) 1.23153(19) 0.35021(17) 0.0530(4) Uani 1 1 d . . .
H3 H 0.2268 1.3374 0.3863 0.064 Uiso 1 1 calc R . .
C4 C 0.0452(2) 1.1973(2) 0.40111(18) 0.0591(4) Uani 1 1 d . . .
H4 H 0.0104 1.2791 0.4702 0.071 Uiso 1 1 calc R . .
C5 C -0.0331(2) 1.0423(2) 0.34987(19) 0.0588(4) Uani 1 1 d . . .
H5 H -0.1213 1.0177 0.3834 0.071 Uiso 1 1 calc R . .
C6 C 0.02117(18) 0.9238(2) 0.24783(17) 0.0508(4) Uani 1 1 d . . .
H6 H -0.0324 0.8186 0.2124 0.061 Uiso 1 1 calc R . .
C7 C 0.37387(17) 1.16442(16) 0.19047(16) 0.0433(3) Uani 1 1 d . . .
C8 C 0.18820(15) 0.81060(16) 0.07595(15) 0.0393(3) Uani 1 1 d . . .
C9 C 0.27588(16) 0.72123(15) 0.10547(15) 0.0401(3) Uani 1 1 d . . .
C10 C 0.27621(19) 0.57668(17) -0.01695(17) 0.0500(4) Uani 1 1 d . . .
H10 H 0.3320 0.5153 0.0009 0.060 Uiso 1 1 calc R . .
C11 C 0.19700(19) 0.52125(18) -0.16340(18) 0.0556(4) Uani 1 1 d . . .
H11 H 0.1987 0.4236 -0.2422 0.067 Uiso 1 1 calc R . .
C12 C 0.11561(19) 0.61104(19) -0.19221(17) 0.0546(4) Uani 1 1 d . . .
H12 H 0.0641 0.5762 -0.2911 0.066 Uiso 1 1 calc R . .
C13 C 0.11093(17) 0.75338(18) -0.07317(16) 0.0486(4) Uani 1 1 d . . .
H13 H 0.0544 0.8130 -0.0932 0.058 Uiso 1 1 calc R . .
C16 C 0.4898(2) 1.3194(2) 0.3150(2) 0.0645(5) Uani 1 1 d . . .
H16A H 0.5147 1.3123 0.4048 0.097 Uiso 1 1 calc R . .
H16B H 0.4446 1.4055 0.3380 0.097 Uiso 1 1 calc R . .
H16C H 0.5830 1.3379 0.2805 0.097 Uiso 1 1 calc R . .
C15 C 0.3199(2) 1.1797(2) 0.0539(2) 0.0635(5) Uani 1 1 d . . .
H15A H 0.4088 1.2140 0.0212 0.095 Uiso 1 1 calc R . .
H15B H 0.2615 1.2562 0.0814 0.095 Uiso 1 1 calc R . .
H15C H 0.2552 1.0786 -0.0275 0.095 Uiso 1 1 calc R . .
C17 C 0.5069(2) 0.7082(2) 0.2624(2) 0.0594(4) Uani 1 1 d . . .
H17A H 0.5723 0.7363 0.2054 0.089 Uiso 1 1 calc R . .
H17B H 0.4719 0.5946 0.2153 0.089 Uiso 1 1 calc R . .
H17C H 0.5649 0.7527 0.3648 0.089 Uiso 1 1 calc R . .
C18 C 0.2587(2) 0.7238(2) 0.3497(2) 0.0676(5) Uani 1 1 d . . .
H18A H 0.3151 0.7614 0.4511 0.101 Uiso 1 1 calc R . .
H18B H 0.2198 0.6101 0.2969 0.101 Uiso 1 1 calc R . .
H18C H 0.1730 0.7689 0.3545 0.101 Uiso 1 1 calc R . .
C14 C 0.36660(17) 0.77306(16) 0.26509(16) 0.0431(3) Uani 1 1 d . . .
O1 O 0.45614(13) 1.04664(13) 0.14253(14) 0.0599(3) Uani 1 1 d . . .
H1 H 0.4868 1.0356 0.2143 0.090 Uiso 1 1 calc R . .
O2 O 0.42729(14) 0.94228(12) 0.34707(12) 0.0605(3) Uani 1 1 d . . .
H2 H 0.3918 0.9796 0.4233 0.091 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 118.88(13) . . ?
C6 C1 C8 114.59(12) . . ?
C2 C1 C8 126.27(12) . . ?
C1 C2 C3 117.37(13) . . ?
C1 C2 C7 124.03(12) . . ?
C3 C2 C7 118.56(13) . . ?
C4 C3 C2 122.70(15) . . ?
C4 C3 H3 118.6 . . ?
C2 C3 H3 118.6 . . ?
C5 C4 C3 119.85(14) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 118.77(15) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 122.41(15) . . ?
C5 C6 H6 118.8 . . ?
C1 C6 H6 118.8 . . ?
O1 C7 C15 107.21(12) . . ?
O1 C7 C16 106.80(13) . . ?
C15 C7 C16 110.17(13) . . ?
O1 C7 C2 110.29(11) . . ?
C15 C7 C2 109.94(12) . . ?
C16 C7 C2 112.26(12) . . ?
C13 C8 C9 118.82(13) . . ?
C13 C8 C1 115.56(12) . . ?
C9 C8 C1 125.18(12) . . ?
C10 C9 C8 117.67(13) . . ?
C10 C9 C14 118.92(12) . . ?
C8 C9 C14 123.38(12) . . ?
C11 C10 C9 122.49(14) . . ?
C11 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
C12 C11 C10 119.57(14) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 119.34(14) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C12 C13 C8 122.07(14) . . ?
C12 C13 H13 119.0 . . ?
C8 C13 H13 119.0 . . ?
C7 C16 H16A 109.5 . . ?
C7 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C7 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O2 C14 C18 108.98(13) . . ?
O2 C14 C17 106.08(12) . . ?
C18 C14 C17 110.06(13) . . ?
O2 C14 C9 108.43(10) . . ?
C18 C14 C9 110.04(12) . . ?
C17 C14 C9 113.10(12) . . ?
C7 O1 H1 109.5 . . ?
C14 O2 H2 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.396(2) . ?
C1 C2 1.399(2) . ?
C1 C8 1.5060(19) . ?
C2 C3 1.398(2) . ?
C2 C7 1.535(2) . ?
C3 C4 1.373(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.4282(17) . ?
C7 C15 1.514(2) . ?
C7 C16 1.524(2) . ?
C8 C13 1.391(2) . ?
C8 C9 1.409(2) . ?
C9 C10 1.394(2) . ?
C9 C14 1.5353(19) . ?
C10 C11 1.377(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.372(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C17 C14 1.525(2) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C14 1.520(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C14 O2 1.4303(17) . ?
O1 H1 0.8200 . ?
O2 H2 0.8200 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.82 2.03 2.7479(17) 146.0 .
O2 H2 O2 0.82 2.40 2.824(2) 113.3 2_676
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.4(2) . . . . ?
C8 C1 C2 C3 175.17(12) . . . . ?
C6 C1 C2 C7 -176.18(12) . . . . ?
C8 C1 C2 C7 -2.4(2) . . . . ?
C1 C2 C3 C4 -0.8(2) . . . . ?
C7 C2 C3 C4 176.88(14) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
C4 C5 C6 C1 0.5(2) . . . . ?
C2 C1 C6 C5 -1.3(2) . . . . ?
C8 C1 C6 C5 -175.80(14) . . . . ?
C1 C2 C7 O1 -27.41(18) . . . . ?
C3 C2 C7 O1 155.08(13) . . . . ?
C1 C2 C7 C15 90.61(16) . . . . ?
C3 C2 C7 C15 -86.90(16) . . . . ?
C1 C2 C7 C16 -146.38(14) . . . . ?
C3 C2 C7 C16 36.11(18) . . . . ?
C6 C1 C8 C13 85.22(16) . . . . ?
C2 C1 C8 C13 -88.83(17) . . . . ?
C6 C1 C8 C9 -87.13(17) . . . . ?
C2 C1 C8 C9 98.83(17) . . . . ?
C13 C8 C9 C10 -2.0(2) . . . . ?
C1 C8 C9 C10 170.12(13) . . . . ?
C13 C8 C9 C14 179.63(12) . . . . ?
C1 C8 C9 C14 -8.3(2) . . . . ?
C8 C9 C10 C11 1.1(2) . . . . ?
C14 C9 C10 C11 179.58(13) . . . . ?
C9 C10 C11 C12 0.8(2) . . . . ?
C10 C11 C12 C13 -1.8(2) . . . . ?
C11 C12 C13 C8 0.9(2) . . . . ?
C9 C8 C13 C12 1.0(2) . . . . ?
C1 C8 C13 C12 -171.83(14) . . . . ?
C10 C9 C14 O2 146.42(13) . . . . ?
C8 C9 C14 O2 -35.22(17) . . . . ?
C10 C9 C14 C18 -94.48(16) . . . . ?
C8 C9 C14 C18 83.88(17) . . . . ?
C10 C9 C14 C17 29.06(18) . . . . ?
C8 C9 C14 C17 -152.58(13) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9197147
