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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/4/02/25/4022510.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_4022510
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            'C30 H34 O2'
_chemical_formula_weight         426.57
_chemical_name_systematic
;
 1,4-bis-(mesitoyl)-2,3,5,6-tetramethylbenzene
;
_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             27/05/2003
_audit_creation_method           SHELXL-97
_cell_angle_alpha                66.8740(10)
_cell_angle_beta                 84.1620(10)
_cell_angle_gamma                76.7850(10)
_cell_formula_units_Z            1
_cell_length_a                   8.4917(4)
_cell_length_b                   8.6147(4)
_cell_length_c                   9.2869(5)
_cell_measurement_temperature    293(2)
_cell_volume                     608.18(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0108
_diffrn_reflns_av_sigmaI/netI    0.0115
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7900
_diffrn_reflns_theta_full        30.01
_diffrn_reflns_theta_max         30.01
_diffrn_reflns_theta_min         2.38
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.9455
_exptl_absorpt_correction_T_min  0.9011
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colouless
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             230
_exptl_crystal_size_max          1.50
_exptl_crystal_size_mid          1.50
_exptl_crystal_size_min          0.80
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.078(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         3530
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0586
_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)+(0.1128P)²+0.0583P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1715
_refine_ls_wR_factor_ref         0.1813
_reflns_number_gt                2983
_reflns_number_total             3530
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo034737tsi20030604_012816.cif
_cod_data_source_block           p-1
_cod_database_code               4022510
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
O1 O 0.11832(13) 0.65199(13) 0.15773(13) 0.0762(4) Uani 1 1 d .
C1 C 0.40007(12) 0.37840(12) 0.03801(11) 0.0386(2) Uani 1 1 d .
C2 C 0.36938(12) 0.50563(12) 0.10113(11) 0.0378(2) Uani 1 1 d .
C3 C 0.46701(13) 0.62783(12) 0.06403(11) 0.0404(2) Uani 1 1 d .
C4 C 0.22073(14) 0.52027(14) 0.20375(13) 0.0449(3) Uani 1 1 d .
C5 C 0.19747(12) 0.37526(13) 0.35477(11) 0.0401(2) Uani 1 1 d .
C6 C 0.32679(13) 0.26987(14) 0.45516(12) 0.0421(2) Uani 1 1 d .
C7 C 0.29451(16) 0.13830(15) 0.59413(13) 0.0502(3) Uani 1 1 d .
H7 H 0.3796 0.0695 0.6610 0.060 Uiso 1 1 calc R
C8 C 0.14036(18) 0.10654(17) 0.63596(15) 0.0564(3) Uani 1 1 d .
C9 C 0.01619(16) 0.20993(18) 0.53557(16) 0.0584(3) Uani 1 1 d .
H9 H -0.0875 0.1884 0.5616 0.070 Uiso 1 1 calc R
C10 C 0.03946(13) 0.34549(16) 0.39658(14) 0.0493(3) Uani 1 1 d .
C11 C 0.29204(16) 0.24938(16) 0.07751(15) 0.0526(3) Uani 1 1 d .
H11A H 0.3405 0.1435 0.1587 0.079 Uiso 1 1 calc R
H11B H 0.2787 0.2279 -0.0140 0.079 Uiso 1 1 calc R
H11C H 0.1883 0.2949 0.1129 0.079 Uiso 1 1 calc R
C12 C 0.4350(2) 0.76096(18) 0.13682(18) 0.0645(4) Uani 1 1 d .
H12A H 0.5343 0.7642 0.1755 0.097 Uiso 1 1 calc R
H12B H 0.3587 0.7312 0.2218 0.097 Uiso 1 1 calc R
H12C H 0.3917 0.8722 0.0595 0.097 Uiso 1 1 calc R
C13 C 0.49923(14) 0.29446(18) 0.42500(16) 0.0552(3) Uani 1 1 d .
H13A H 0.5631 0.2196 0.5153 0.083 Uiso 1 1 calc R
H13B H 0.5017 0.4122 0.4043 0.083 Uiso 1 1 calc R
H13C H 0.5425 0.2673 0.3362 0.083 Uiso 1 1 calc R
C14 C 0.1078(3) -0.0339(2) 0.7890(2) 0.0859(5) Uani 1 1 d .
H14A H 0.0609 0.0166 0.8631 0.129 Uiso 1 1 calc R
H14B H 0.2076 -0.1130 0.8292 0.129 Uiso 1 1 calc R
H14C H 0.0343 -0.0946 0.7720 0.129 Uiso 1 1 calc R
C15 C -0.10625(16) 0.4492(2) 0.2967(2) 0.0739(4) Uani 1 1 d .
H15A H -0.1966 0.3943 0.3376 0.111 Uiso 1 1 calc R
H15B H -0.0832 0.4561 0.1913 0.111 Uiso 1 1 calc R
H15C H -0.1319 0.5632 0.2976 0.111 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
C2 C1 C3 118.96(8) . 2_665
C2 C1 C11 121.02(9) . .
C3 C1 C11 120.03(9) 2_665 .
C1 C2 C3 121.77(9) . .
C1 C2 C4 119.43(9) . .
C3 C2 C4 118.68(9) . .
C1 C3 C2 119.27(9) 2_665 .
C1 C3 C12 119.63(9) 2_665 .
C2 C3 C12 121.05(9) . .
O1 C4 C5 120.73(9) . .
O1 C4 C2 117.75(9) . .
C5 C4 C2 121.48(9) . .
C6 C5 C10 119.55(9) . .
C6 C5 C4 122.42(9) . .
C10 C5 C4 118.03(9) . .
C7 C6 C5 118.77(10) . .
C7 C6 C13 117.22(10) . .
C5 C6 C13 123.96(10) . .
C8 C7 C6 122.31(11) . .
C9 C8 C7 117.94(10) . .
C9 C8 C14 120.73(13) . .
C7 C8 C14 121.31(14) . .
C8 C9 C10 122.69(11) . .
C9 C10 C5 118.71(11) . .
C9 C10 C15 117.60(11) . .
C5 C10 C15 123.66(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C4 1.2125(14) .
C1 C2 1.3985(14) .
C1 C3 1.4034(14) 2_665
C1 C11 1.5129(14) .
C2 C3 1.4037(13) .
C2 C4 1.5148(13) .
C3 C1 1.4034(14) 2_665
C3 C12 1.5084(14) .
C4 C5 1.4990(14) .
C5 C6 1.4096(15) .
C5 C10 1.4107(14) .
C6 C7 1.3952(15) .
C6 C13 1.5098(16) .
C7 C8 1.3843(18) .
C8 C9 1.376(2) .
C8 C14 1.5108(17) .
C9 C10 1.3923(16) .
C10 C15 1.5054(18) .
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
C3 C1 C2 C3 0.57(17) 2_665 .
C11 C1 C2 C3 -179.10(10) . .
C3 C1 C2 C4 176.42(9) 2_665 .
C11 C1 C2 C4 -3.25(15) . .
C1 C2 C3 C1 -0.58(17) . 2_665
C4 C2 C3 C1 -176.45(9) . 2_665
C1 C2 C3 C12 -178.21(11) . .
C4 C2 C3 C12 5.91(16) . .
C1 C2 C4 O1 -116.49(14) . .
C3 C2 C4 O1 59.48(16) . .
C1 C2 C4 C5 61.57(14) . .
C3 C2 C4 C5 -122.46(11) . .
O1 C4 C5 C6 -144.73(14) . .
C2 C4 C5 C6 37.27(16) . .
O1 C4 C5 C10 34.94(18) . .
C2 C4 C5 C10 -143.06(11) . .
C10 C5 C6 C7 -0.08(17) . .
C4 C5 C6 C7 179.58(10) . .
C10 C5 C6 C13 -177.59(11) . .
C4 C5 C6 C13 2.07(17) . .
C5 C6 C7 C8 0.72(18) . .
C13 C6 C7 C8 178.39(12) . .
C6 C7 C8 C9 -0.1(2) . .
C6 C7 C8 C14 -178.47(13) . .
C7 C8 C9 C10 -1.2(2) . .
C14 C8 C9 C10 177.21(14) . .
C8 C9 C10 C5 1.8(2) . .
C8 C9 C10 C15 179.99(14) . .
C6 C5 C10 C9 -1.10(18) . .
C4 C5 C10 C9 179.22(11) . .
C6 C5 C10 C15 -179.21(13) . .
C4 C5 C10 C15 1.1(2) . .
