#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/42/2204256.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_2204256
loop_
_publ_author_name
'Xu, Jiyang'
'Côté, Adrien P.'
'Chen, Banglin'
_publ_section_title
;
 3,3',5,5'-Tetramethylterphenyl
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1697
_journal_page_last               o1698
_journal_paper_doi               10.1107/S1600536804021282
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C22 H22'
_chemical_formula_moiety         'C22 H22'
_chemical_formula_sum            'C22 H22'
_chemical_formula_weight         286.42
_chemical_name_common            'tetramethyl terphenyl'
_chemical_name_systematic
;
3,3',5,5'-tetramethylterphenyl
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.381(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.9264(13)
_cell_length_b                   9.2297(10)
_cell_length_c                   7.6075(8)
_cell_measurement_reflns_used    4518
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      2.2
_cell_volume                     807.42(15)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2003)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7844
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         1.77
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.159
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.743
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1854
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.743
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0469
_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)+(0.2P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1657
_refine_ls_wR_factor_ref         0.1766
_reflns_number_gt                1574
_reflns_number_total             1854
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ac6115.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2204256
_cod_database_fobs_code          2204256
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_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_type_symbol
C1 0.82181(10) 0.02648(11) 0.19561(15) 0.0227(3) Uani d . 1 C
C2 0.71838(9) 0.09919(12) 0.11479(15) 0.0258(3) Uani d . 1 C
H2 0.7092 0.1451 0.0001 0.031 Uiso calc R 1 H
C3 0.62783(10) 0.10549(12) 0.20013(16) 0.0273(3) Uani d . 1 C
C4 0.64374(10) 0.03779(12) 0.36792(15) 0.0268(3) Uani d . 1 C
H4 0.5827 0.0412 0.4265 0.032 Uiso calc R 1 H
C5 0.74577(10) -0.03483(12) 0.45331(14) 0.0247(3) Uani d . 1 C
C6 0.83499(9) -0.03869(12) 0.36554(15) 0.0238(3) Uani d . 1 C
H6 0.9058 -0.0865 0.4226 0.029 Uiso calc R 1 H
C7 0.91431(9) 0.01446(11) 0.09792(14) 0.0224(3) Uani d . 1 C
C8 0.98528(9) -0.10877(12) 0.11664(14) 0.0242(3) Uani d . 1 C
H8 0.9760 -0.1841 0.1968 0.029 Uiso calc R 1 H
C9 0.93132(9) 0.12317(12) -0.02080(14) 0.0242(3) Uani d . 1 C
H9 0.8849 0.2083 -0.0360 0.029 Uiso calc R 1 H
C10 0.51516(11) 0.18216(15) 0.11082(18) 0.0362(4) Uani d . 1 C
H10A 0.4510 0.1348 0.1464 0.054 Uiso calc R 1 H
H10B 0.5010 0.1778 -0.0220 0.054 Uiso calc R 1 H
H10C 0.5204 0.2836 0.1501 0.054 Uiso calc R 1 H
C11 0.75836(11) -0.11035(14) 0.63288(17) 0.0334(3) Uani d . 1 C
H11A 0.7087 -0.0627 0.6995 0.050 Uiso calc R 1 H
H11B 0.8396 -0.1055 0.7051 0.050 Uiso calc R 1 H
H11C 0.7350 -0.2120 0.6110 0.050 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0253(6) 0.0212(5) 0.0236(6) -0.0028(4) 0.0100(4) -0.0029(4)
C2 0.0287(6) 0.0265(6) 0.0243(6) 0.0014(4) 0.0109(5) 0.0020(4)
C3 0.0271(6) 0.0259(6) 0.0306(7) 0.0011(4) 0.0107(5) -0.0007(4)
C4 0.0285(6) 0.0256(6) 0.0305(6) -0.0023(4) 0.0154(5) -0.0026(4)
C5 0.0294(6) 0.0239(6) 0.0232(6) -0.0039(4) 0.0111(4) -0.0027(4)
C6 0.0251(6) 0.0238(6) 0.0235(6) -0.0008(4) 0.0084(4) -0.0016(4)
C7 0.0238(6) 0.0234(6) 0.0211(6) -0.0019(4) 0.0078(4) -0.0010(4)
C8 0.0281(6) 0.0225(6) 0.0240(6) -0.0012(4) 0.0103(5) 0.0026(4)
C9 0.0273(6) 0.0221(6) 0.0248(6) 0.0012(4) 0.0095(5) 0.0007(4)
C10 0.0314(7) 0.0420(8) 0.0380(7) 0.0091(5) 0.0140(5) 0.0100(5)
C11 0.0343(7) 0.0407(7) 0.0284(7) 0.0004(5) 0.0139(5) 0.0048(5)
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'
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
C2 C1 C6 . 118.97(10)
C2 C1 C7 . 120.08(10)
C6 C1 C7 . 120.91(10)
C1 C2 C3 . 121.04(10)
C1 C2 H2 . 119.5
C3 C2 H2 . 119.5
C4 C3 C2 . 118.24(10)
C4 C3 C10 . 120.83(10)
C2 C3 C10 . 120.92(10)
C3 C4 C5 . 122.41(10)
C3 C4 H4 . 118.8
C5 C4 H4 . 118.8
C4 C5 C6 . 118.14(10)
C4 C5 C11 . 120.77(10)
C6 C5 C11 . 121.07(10)
C1 C6 C5 . 121.19(10)
C1 C6 H6 . 119.4
C5 C6 H6 . 119.4
C9 C7 C8 . 117.37(10)
C9 C7 C1 . 121.46(9)
C8 C7 C1 . 121.13(9)
C9 C8 C7 3_755 121.48(10)
C9 C8 H8 3_755 119.3
C7 C8 H8 . 119.3
C8 C9 C7 3_755 121.15(10)
C8 C9 H9 3_755 119.4
C7 C9 H9 . 119.4
C3 C10 H10A . 109.5
C3 C10 H10B . 109.5
H10A C10 H10B . 109.5
C3 C10 H10C . 109.5
H10A C10 H10C . 109.5
H10B C10 H10C . 109.5
C5 C11 H11A . 109.5
C5 C11 H11B . 109.5
H11A C11 H11B . 109.5
C5 C11 H11C . 109.5
H11A C11 H11C . 109.5
H11B C11 H11C . 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 . 1.3964(15)
C1 C2 . 1.3956(15)
C1 C7 . 1.4888(15)
C2 C3 . 1.4011(15)
C2 H2 . 0.9500
C3 C4 . 1.3883(16)
C3 C10 . 1.5113(16)
C4 C5 . 1.3901(16)
C4 H4 . 0.9500
C5 C6 . 1.3987(14)
C5 C11 . 1.5053(16)
C6 H6 . 0.9500
C7 C8 . 1.4023(15)
C7 C9 . 1.4003(15)
C8 C9 3_755 1.3868(15)
C8 H8 . 0.9500
C9 C8 3_755 1.3869(15)
C9 H9 . 0.9500
C10 H10A . 0.9800
C10 H10B . 0.9800
C10 H10C . 0.9800
C11 H11A . 0.9800
C11 H11B . 0.9800
C11 H11C . 0.9800
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_4
_geom_torsion
C6 C1 C2 C3 . -1.00(16)
C7 C1 C2 C3 . 176.73(9)
C1 C2 C3 C4 . 0.21(16)
C1 C2 C3 C10 . -178.97(11)
C2 C3 C4 C5 . 0.23(17)
C10 C3 C4 C5 . 179.41(11)
C3 C4 C5 C6 . 0.13(17)
C3 C4 C5 C11 . -178.31(10)
C2 C1 C6 C5 . 1.38(16)
C7 C1 C6 C5 . -176.33(9)
C4 C5 C6 C1 . -0.95(16)
C11 C5 C6 C1 . 177.49(10)
C6 C1 C7 C8 . 31.59(15)
C2 C1 C7 C8 . -146.10(11)
C6 C1 C7 C9 . -150.61(11)
C2 C1 C7 C9 . 31.70(15)
C9 C7 C8 C9 3_755 -0.35(17)
C1 C7 C8 C9 3_755 177.53(9)
C8 C7 C9 C8 3_755 0.35(17)
C1 C7 C9 C8 3_755 -177.53(9)
