#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:52:29 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179676 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/28/4512869.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_4512869
loop_
_publ_author_name
'Neogi, Ishita'
'Bajpai, Alankriti'
'Savitha, Govardhan'
'Moorthy, Jarugu Narasimha'
_publ_section_title
;
 Tetraarylbiphenyl as a New Lattice Inclusion Host by Structure
 Reductionism: Shape and Size Complementarity Based on Torsional
 Flexibility
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2129
_journal_paper_doi               10.1021/cg501711t
_journal_volume                  15
_journal_year                    2015
_chemical_compound_source        synthetic
_chemical_formula_moiety         'C48 H50 O4'
_chemical_formula_sum            'C48 H50 O4'
_chemical_formula_weight         690.88
_chemical_name_common            TB
_chemical_name_systematic
3,3,5,5-Tetrakis(2,6-dimethyl-4-methoxyphenyl)biphenyl
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      60
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.545(3)
_cell_length_b                   14.082(4)
_cell_length_c                   23.811(6)
_cell_measurement_reflns_used    1541
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      2.26
_cell_volume                     3871.1(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    SHELX-97
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0776
_diffrn_reflns_av_unetI/netI     0.0718
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            23897
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.347
_diffrn_reflns_theta_min         2.281
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       square
_exptl_crystal_F_000             1480
_exptl_crystal_recrystallization_method evaporation
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.129
_refine_ls_extinction_coef       0.0068(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         4780
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0945
_refine_ls_R_factor_gt           0.0618
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1031P)²+0.7334P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1550
_refine_ls_wR_factor_ref         0.1886
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3416
_reflns_number_total             4780
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg501711t_si_002.cif
_cod_data_source_block           TB-GF
_cod_depositor_comments
'Adding full bibliography for 4512869--4512878.cif.'
_cod_original_cell_volume        3871.1(17)
_cod_database_code               4512869
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2014-1
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.6007(2) 0.48582(17) 0.05068(9) 0.0483(6) Uani 1 1 d . .
H1A H 0.6497 0.4951 0.0186 0.072 Uiso 1 1 calc R U
H1B H 0.6450 0.4948 0.0844 0.072 Uiso 1 1 calc R U
H1C H 0.5383 0.5308 0.0497 0.072 Uiso 1 1 calc R U
O1 O 0.55482(11) 0.39202(10) 0.04978(6) 0.0364(4) Uani 1 1 d . .
C3 C 0.44117(15) 0.27366(12) 0.09098(8) 0.0263(4) Uani 1 1 d . .
H3 H 0.4606 0.2348 0.0608 0.032 Uiso 1 1 calc R U
O2 O 0.38953(11) 0.07155(9) 0.52795(5) 0.0273(3) Uani 1 1 d . .
C2 C 0.48583(14) 0.36549(13) 0.09382(8) 0.0276(4) Uani 1 1 d . .
C4 C 0.36805(14) 0.23958(12) 0.13258(7) 0.0252(4) Uani 1 1 d . .
C5 C 0.33904(14) 0.29783(12) 0.17839(7) 0.0237(4) Uani 1 1 d . .
C006 C 0.23874(15) 0.21843(12) 0.42227(7) 0.0255(4) Uani 1 1 d . .
C6 C 0.38372(15) 0.39070(13) 0.18093(7) 0.0271(4) Uani 1 1 d . .
C7 C 0.45696(15) 0.42371(12) 0.13850(7) 0.0287(4) Uani 1 1 d . .
H7 H 0.4865 0.4851 0.1403 0.034 Uiso 1 1 calc R U
C9 C 0.31779(17) 0.14056(13) 0.12686(9) 0.0344(4) Uani 1 1 d . .
H9A H 0.3274 0.1068 0.1616 0.052 Uiso 1 1 calc R U
H9B H 0.3573 0.1072 0.0973 0.052 Uiso 1 1 calc R U
H9C H 0.2368 0.1449 0.1180 0.052 Uiso 1 1 calc R U
C8 C 0.34968(18) 0.45692(14) 0.22776(8) 0.0356(4) Uani 1 1 d . .
H8A H 0.3822 0.5186 0.2210 0.053 Uiso 1 1 calc R U
H8B H 0.3783 0.4327 0.2628 0.053 Uiso 1 1 calc R U
H8C H 0.2668 0.4617 0.2294 0.053 Uiso 1 1 calc R U
C10 C 0.25913(14) 0.26258(11) 0.22311(7) 0.0234(4) Uani 1 1 d . .
C11 C 0.30215(14) 0.23625(12) 0.27562(7) 0.0251(4) Uani 1 1 d . .
H11 H 0.3811 0.2411 0.2827 0.030 Uiso 1 1 calc R U
C13 C 0.10960(14) 0.19745(12) 0.30648(7) 0.0240(4) Uani 1 1 d . .
H13 H 0.0601 0.1745 0.3341 0.029 Uiso 1 1 calc R U
C12 C 0.22862(14) 0.20278(12) 0.31765(7) 0.0235(4) Uani 1 1 d . .
C14 C 0.06380(14) 0.22558(12) 0.25519(7) 0.0230(4) Uani 1 1 d . .
C21 C 0.1618(2) 0.30571(15) 0.42109(9) 0.0400(5) Uani 1 1 d . .
H21A H 0.1789 0.3426 0.3882 0.060 Uiso 1 1 calc R U
H21B H 0.1758 0.3433 0.4540 0.060 Uiso 1 1 calc R U
H21C H 0.0821 0.2865 0.4203 0.060 Uiso 1 1 calc R U
C22 C 0.39625(17) 0.04331(14) 0.32632(7) 0.0322(4) Uani 1 1 d . .
H22A H 0.3336 0.0339 0.3004 0.048 Uiso 1 1 calc R U
H22B H 0.4272 -0.0172 0.3373 0.048 Uiso 1 1 calc R U
H22C H 0.4559 0.0803 0.3087 0.048 Uiso 1 1 calc R U
C23 C 0.34573(16) 0.11275(13) 0.57799(7) 0.0286(4) Uani 1 1 d . .
H23A H 0.3796 0.0817 0.6099 0.043 Uiso 1 1 calc R U
H23B H 0.2631 0.1053 0.5791 0.043 Uiso 1 1 calc R U
H23C H 0.3648 0.1791 0.5788 0.043 Uiso 1 1 calc R U
C20 C 0.27635(15) 0.18653(12) 0.47467(7) 0.0249(4) Uani 1 1 d . .
H20 H 0.2520 0.2173 0.5072 0.030 Uiso 1 1 calc R U
C19 C 0.34997(14) 0.10908(12) 0.47828(7) 0.0222(4) Uani 1 1 d . .
C18 C 0.38895(14) 0.06445(11) 0.42983(7) 0.0224(4) Uani 1 1 d . .
H18 H 0.4401 0.0136 0.4326 0.027 Uiso 1 1 calc R U
C17 C 0.35237(14) 0.09499(12) 0.37749(7) 0.0225(4) Uani 1 1 d . .
C16 C 0.27462(14) 0.17222(11) 0.37331(7) 0.0227(4) Uani 1 1 d . .
C15 C 0.13984(14) 0.25666(12) 0.21364(7) 0.0233(4) Uani 1 1 d . .
H15 H 0.1105 0.2739 0.1787 0.028 Uiso 1 1 calc R U
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'
O O 0.0106 0.0060 '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'
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_3
O1 C1 H1A 109.5 .
O1 C1 H1B 109.5 .
H1A C1 H1B 109.5 .
O1 C1 H1C 109.5 .
H1A C1 H1C 109.5 .
H1B C1 H1C 109.5 .
C2 O1 C1 117.29(16) .
C4 C3 C2 120.76(17) .
C4 C3 H3 119.6 .
C2 C3 H3 119.6 .
C19 O2 C23 116.57(13) .
O1 C2 C7 124.57(16) .
O1 C2 C3 115.56(16) .
C7 C2 C3 119.86(16) .
C3 C4 C5 119.83(16) .
C3 C4 C9 119.13(16) .
C5 C4 C9 121.02(15) .
C4 C5 C6 119.25(15) .
C4 C5 C10 120.43(15) .
C6 C5 C10 120.30(15) .
C20 C006 C16 120.24(15) .
C20 C006 C21 117.37(15) .
C16 C006 C21 122.37(15) .
C7 C6 C5 120.00(16) .
C7 C6 C8 119.17(16) .
C5 C6 C8 120.78(16) .
C2 C7 C6 120.30(16) .
C2 C7 H7 119.8 .
C6 C7 H7 119.8 .
C4 C9 H9A 109.5 .
C4 C9 H9B 109.5 .
H9A C9 H9B 109.5 .
C4 C9 H9C 109.5 .
H9A C9 H9C 109.5 .
H9B C9 H9C 109.5 .
C6 C8 H8A 109.5 .
C6 C8 H8B 109.5 .
H8A C8 H8B 109.5 .
C6 C8 H8C 109.5 .
H8A C8 H8C 109.5 .
H8B C8 H8C 109.5 .
C11 C10 C15 118.64(15) .
C11 C10 C5 120.48(15) .
C15 C10 C5 120.87(15) .
C12 C11 C10 121.07(15) .
C12 C11 H11 119.5 .
C10 C11 H11 119.5 .
C14 C13 C12 121.66(15) .
C14 C13 H13 119.2 .
C12 C13 H13 119.2 .
C11 C12 C13 118.61(15) .
C11 C12 C16 121.24(15) .
C13 C12 C16 120.15(15) .
C13 C14 C15 118.31(15) .
C13 C14 C14 121.40(18) 4
C15 C14 C14 120.26(17) 4
C006 C21 H21A 109.5 .
C006 C21 H21B 109.5 .
H21A C21 H21B 109.5 .
C006 C21 H21C 109.5 .
H21A C21 H21C 109.5 .
H21B C21 H21C 109.5 .
C17 C22 H22A 109.5 .
C17 C22 H22B 109.5 .
H22A C22 H22B 109.5 .
C17 C22 H22C 109.5 .
H22A C22 H22C 109.5 .
H22B C22 H22C 109.5 .
O2 C23 H23A 109.5 .
O2 C23 H23B 109.5 .
H23A C23 H23B 109.5 .
O2 C23 H23C 109.5 .
H23A C23 H23C 109.5 .
H23B C23 H23C 109.5 .
C19 C20 C006 119.99(15) .
C19 C20 H20 120.0 .
C006 C20 H20 120.0 .
O2 C19 C20 124.09(15) .
O2 C19 C18 115.68(14) .
C20 C19 C18 120.23(15) .
C17 C18 C19 120.56(15) .
C17 C18 H18 119.7 .
C19 C18 H18 119.7 .
C18 C17 C16 119.73(15) .
C18 C17 C22 118.38(15) .
C16 C17 C22 121.89(15) .
C006 C16 C17 119.19(15) .
C006 C16 C12 120.08(14) .
C17 C16 C12 120.70(15) .
C14 C15 C10 121.66(15) .
C14 C15 H15 119.2 .
C10 C15 H15 119.2 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.423(2) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
O1 C2 1.369(2) .
C3 C4 1.387(2) .
C3 C2 1.394(3) .
C3 H3 0.9300 .
O2 C19 1.3735(19) .
O2 C23 1.419(2) .
C2 C7 1.384(3) .
C4 C5 1.405(2) .
C4 C9 1.517(2) .
C5 C6 1.407(2) .
C5 C10 1.494(2) .
C006 C20 1.395(2) .
C006 C16 1.398(2) .
C006 C21 1.517(3) .
C6 C7 1.397(2) .
C6 C8 1.506(3) .
C7 H7 0.9300 .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C10 C11 1.396(2) .
C10 C15 1.398(2) .
C11 C12 1.394(2) .
C11 H11 0.9300 .
C13 C14 1.389(2) .
C13 C12 1.401(2) .
C13 H13 0.9300 .
C12 C16 1.491(2) .
C14 C15 1.393(2) .
C14 C14 1.494(3) 4
C21 H21A 0.9600 .
C21 H21B 0.9600 .
C21 H21C 0.9600 .
C22 C17 1.507(2) .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 0.9600 .
C23 H23A 0.9600 .
C23 H23B 0.9600 .
C23 H23C 0.9600 .
C20 C19 1.385(2) .
C20 H20 0.9300 .
C19 C18 1.389(2) .
C18 C17 1.384(2) .
C18 H18 0.9300 .
C17 C16 1.414(2) .
C15 H15 0.9300 .
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_4
C1 O1 C2 C7 0.7(3) . .
C1 O1 C2 C3 179.06(16) . .
C4 C3 C2 O1 -178.57(15) . .
C4 C3 C2 C7 -0.1(3) . .
C2 C3 C4 C5 -0.4(3) . .
C2 C3 C4 C9 177.77(16) . .
C3 C4 C5 C6 0.8(2) . .
C9 C4 C5 C6 -177.36(16) . .
C3 C4 C5 C10 179.17(15) . .
C9 C4 C5 C10 1.0(2) . .
C4 C5 C6 C7 -0.6(2) . .
C10 C5 C6 C7 -179.00(15) . .
C4 C5 C6 C8 176.81(16) . .
C10 C5 C6 C8 -1.6(2) . .
O1 C2 C7 C6 178.61(16) . .
C3 C2 C7 C6 0.3(3) . .
C5 C6 C7 C2 0.1(3) . .
C8 C6 C7 C2 -177.41(16) . .
C4 C5 C10 C11 105.50(19) . .
C6 C5 C10 C11 -76.2(2) . .
C4 C5 C10 C15 -75.5(2) . .
C6 C5 C10 C15 102.8(2) . .
C15 C10 C11 C12 1.3(2) . .
C5 C10 C11 C12 -179.68(15) . .
C10 C11 C12 C13 -1.0(2) . .
C10 C11 C12 C16 178.40(15) . .
C14 C13 C12 C11 -0.8(2) . .
C14 C13 C12 C16 179.79(15) . .
C12 C13 C14 C15 2.2(2) . .
C12 C13 C14 C14 -176.04(12) . 4
C16 C006 C20 C19 0.3(3) . .
C21 C006 C20 C19 -177.82(17) . .
C23 O2 C19 C20 3.6(2) . .
C23 O2 C19 C18 -176.63(15) . .
C006 C20 C19 O2 -178.64(15) . .
C006 C20 C19 C18 1.7(3) . .
O2 C19 C18 C17 178.48(14) . .
C20 C19 C18 C17 -1.8(3) . .
C19 C18 C17 C16 0.0(2) . .
C19 C18 C17 C22 -179.29(15) . .
C20 C006 C16 C17 -2.1(3) . .
C21 C006 C16 C17 175.92(17) . .
C20 C006 C16 C12 176.28(16) . .
C21 C006 C16 C12 -5.7(3) . .
C18 C17 C16 C006 2.0(2) . .
C22 C17 C16 C006 -178.80(16) . .
C18 C17 C16 C12 -176.40(15) . .
C22 C17 C16 C12 2.8(2) . .
C11 C12 C16 C006 119.26(18) . .
C13 C12 C16 C006 -61.3(2) . .
C11 C12 C16 C17 -62.4(2) . .
C13 C12 C16 C17 117.05(18) . .
C13 C14 C15 C10 -1.9(3) . .
C14 C14 C15 C10 176.35(13) 4 .
C11 C10 C15 C14 0.2(2) . .
C5 C10 C15 C14 -178.82(15) . .
