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#$Date: 2016-03-21 02:44:46 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178404 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/25/4022508.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_4022508
loop_
_publ_author_name
'Carmine Coluccini'
'Stefano Grilli'
'Lodovico Lunazzi'
'Andrea Mazzanti'
_publ_contact_author
;
Dr. Andrea Mazzanti
Universita di Bologna
Dipartimento di Chimica Organica 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
;
 Conformational Studies by Dynamic NMR. 94.
 Cogwheel Pathway for the Stereomutations of Durene
 Derivatives Containing the Mesityl Ring
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7266
_journal_page_last               7273
_journal_paper_doi               10.1021/jo034737t
_journal_volume                  68
_journal_year                    2003
_chemical_formula_sum            'C32 H38'
_chemical_formula_weight         422.62
_chemical_melting_point          190
_chemical_name_systematic
;
 1,4-bis-(mesitylethenyl)-2,3,5,6-tetramethylbenzene
;
_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_date             03/04/2003
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.9630(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.6705(6)
_cell_length_b                   6.4311(3)
_cell_length_c                   14.8119(6)
_cell_measurement_temperature    293(2)
_cell_volume                     1269.02(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0205
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15727
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         1.53
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  0.9757
_exptl_absorpt_correction_T_min  0.9523
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.106
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cubic
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         3694
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0582
_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)+(0.1124P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1849
_refine_ls_wR_factor_ref         0.1994
_reflns_number_gt                2362
_reflns_number_total             3694
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo034737tsi20030604_012649.cif
_cod_data_source_block           mono
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4022508
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_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
C1 C 0.92026(8) 0.13790(18) 0.46518(8) 0.0480(3) Uani 1 1 d .
C2 C 1.00226(9) 0.12496(19) 0.42276(8) 0.0504(3) Uani 1 1 d .
C3 C 0.91863(9) 0.01235(18) 0.54306(8) 0.0489(3) Uani 1 1 d .
C4 C 0.72964(9) 0.20202(19) 0.40085(8) 0.0512(3) Uani 1 1 d .
C5 C 0.83474(9) 0.28553(19) 0.42938(9) 0.0537(3) Uani 1 1 d .
C6 C 0.70725(10) 0.0388(2) 0.33594(9) 0.0548(3) Uani 1 1 d .
C7 C 0.65149(10) 0.2827(2) 0.43844(9) 0.0608(4) Uani 1 1 d .
C8 C 0.53435(11) 0.0268(3) 0.35389(11) 0.0675(4) Uani 1 1 d .
C9 C 0.78231(12) -0.0385(3) 0.28298(11) 0.0675(4) Uani 1 1 d .
H9A H 0.7519 -0.1445 0.2401 0.101 Uiso 1 1 calc R
H9B H 0.8396 -0.0951 0.3255 0.101 Uiso 1 1 calc R
H9C H 0.8032 0.0749 0.2496 0.101 Uiso 1 1 calc R
C10 C 0.83343(10) 0.0280(3) 0.59234(10) 0.0665(4) Uani 1 1 d .
H10A H 0.7883 -0.0868 0.5745 0.100 Uiso 1 1 calc R
H10B H 0.7980 0.1562 0.5758 0.100 Uiso 1 1 calc R
H10C H 0.8599 0.0244 0.6581 0.100 Uiso 1 1 calc R
C11 C 0.55671(11) 0.1916(3) 0.41431(10) 0.0685(4) Uani 1 1 d .
H11 H 0.5060 0.2447 0.4403 0.082 Uiso 1 1 calc R
C12 C 0.61085(11) -0.0448(2) 0.31453(10) 0.0648(4) Uani 1 1 d .
H12 H 0.5973 -0.1532 0.2720 0.078 Uiso 1 1 calc R
C13 C 1.00744(11) 0.2542(3) 0.33811(10) 0.0729(4) Uani 1 1 d .
H13A H 1.0626 0.3499 0.3536 0.109 Uiso 1 1 calc R
H13B H 0.9460 0.3303 0.3181 0.109 Uiso 1 1 calc R
H13C H 1.0171 0.1642 0.2891 0.109 Uiso 1 1 calc R
C14 C 0.66420(14) 0.4636(3) 0.50502(13) 0.0816(5) Uani 1 1 d .
H14A H 0.6495 0.5909 0.4709 0.122 Uiso 1 1 calc R
H14B H 0.7321 0.4671 0.5407 0.122 Uiso 1 1 calc R
H14C H 0.6191 0.4478 0.5458 0.122 Uiso 1 1 calc R
C15 C 0.43094(13) -0.0685(4) 0.32998(14) 0.0934(6) Uani 1 1 d .
H15A H 0.3883 0.0018 0.3635 0.140 Uiso 1 1 calc R
H15B H 0.4352 -0.2130 0.3465 0.140 Uiso 1 1 calc R
H15C H 0.4035 -0.0548 0.2647 0.140 Uiso 1 1 calc R
C16 C 0.85147(12) 0.4868(2) 0.42473(13) 0.0789(5) Uani 1 1 d .
H16A H 0.7982 0.5773 0.4038 0.095 Uiso 1 1 calc R
H16B H 0.9166 0.5381 0.4424 0.095 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'
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
C2 C1 C3 119.46(10) .
C2 C1 C5 120.91(10) .
C3 C1 C5 119.63(11) .
C3 C2 C1 120.31(10) 3_756
C3 C2 C13 117.92(11) 3_756
C1 C2 C13 121.76(11) .
C2 C3 C1 120.23(11) 3_756
C2 C3 C10 118.95(11) 3_756
C1 C3 C10 120.79(11) .
C6 C4 C7 118.38(12) .
C6 C4 C5 120.36(11) .
C7 C4 C5 121.25(12) .
C16 C5 C4 120.14(12) .
C16 C5 C1 120.44(12) .
C4 C5 C1 119.41(10) .
C12 C6 C4 119.50(13) .
C12 C6 C9 118.27(13) .
C4 C6 C9 122.07(12) .
C11 C7 C4 119.17(13) .
C11 C7 C14 117.11(13) .
C4 C7 C14 123.72(13) .
C11 C8 C12 116.80(13) .
C11 C8 C15 121.69(16) .
C12 C8 C15 121.50(16) .
C8 C11 C7 123.27(14) .
C8 C12 C6 122.76(14) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.4051(17) .
C1 C3 1.4123(16) .
C1 C5 1.5071(16) .
C2 C3 1.4000(16) 3_756
C2 C13 1.5192(17) .
C3 C2 1.4000(16) 3_756
C3 C10 1.5102(17) .
C4 C6 1.4099(18) .
C4 C7 1.4098(19) .
C4 C5 1.5029(17) .
C5 C16 1.319(2) .
C6 C12 1.3924(19) .
C6 C9 1.509(2) .
C7 C11 1.394(2) .
C7 C14 1.510(2) .
C8 C11 1.376(2) .
C8 C12 1.385(2) .
C8 C15 1.508(2) .
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_4
C3 C1 C2 C3 0.47(18) 3_756
C5 C1 C2 C3 179.78(10) 3_756
C3 C1 C2 C13 179.22(12) .
C5 C1 C2 C13 -1.47(18) .
C2 C1 C3 C2 -0.47(18) 3_756
C5 C1 C3 C2 -179.78(10) 3_756
C2 C1 C3 C10 177.82(12) .
C5 C1 C3 C10 -1.50(17) .
C6 C4 C5 C16 127.57(16) .
C7 C4 C5 C16 -53.0(2) .
C6 C4 C5 C1 -53.74(16) .
C7 C4 C5 C1 125.73(14) .
C2 C1 C5 C16 -58.13(19) .
C3 C1 C5 C16 121.18(16) .
C2 C1 C5 C4 123.18(13) .
C3 C1 C5 C4 -57.52(15) .
C7 C4 C6 C12 -3.29(19) .
C5 C4 C6 C12 176.19(12) .
C7 C4 C6 C9 171.96(13) .
C5 C4 C6 C9 -8.56(18) .
C6 C4 C7 C11 3.5(2) .
C5 C4 C7 C11 -175.98(11) .
C6 C4 C7 C14 -177.05(13) .
C5 C4 C7 C14 3.5(2) .
C12 C8 C11 C7 -1.7(2) .
C15 C8 C11 C7 179.60(15) .
C4 C7 C11 C8 -1.0(2) .
C14 C7 C11 C8 179.50(14) .
C11 C8 C12 C6 1.9(2) .
C15 C8 C12 C6 -179.38(15) .
C4 C6 C12 C8 0.6(2) .
C9 C6 C12 C8 -174.86(14) .
