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#$Date: 2016-03-21 03:41:24 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178438 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/59/4025925.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_4025925
loop_
_publ_author_name
'Curtis J. Rieder'
'Karl J. Winberg'
'F. G. West'
_publ_contact_author_address
; Department of Chemistry
  University of Alberta
  Edmonton, Alberta T6G 2G2
  Canada
;
_publ_contact_author_email       frederick.west@ualberta.ca
_publ_contact_author_fax         1(780)4928231
_publ_contact_author_name        'Dr. Frederick G. West'
_publ_section_title
;
 Olefination of α,α'-Divinyl Ketones through Catalytic Meyer-Schuster
 Rearrangement
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              50
_journal_page_last               56
_journal_paper_doi               10.1021/jo101497f
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C27 H22'
_chemical_formula_sum            'C27 H22'
_chemical_formula_weight         346.45
_chemical_name_systematic
3,4-diphenyl-2-methyl-5-methylidene-1-phenylethynylcyclopent-1-ene
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.8798(11)
_cell_length_b                   15.0260(11)
_cell_length_c                   8.5564(6)
_cell_measurement_reflns_used    5565
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.29
_cell_measurement_theta_min      2.57
_cell_volume                     2041.6(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω 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  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13849
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  0.9895
_exptl_absorpt_correction_T_min  0.9818
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.127
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.025
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         1905
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0337
_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)+(0.0334P)²+0.4303P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0869
_reflns_number_gt                1544
_reflns_number_total             1905
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo101497f_si_001.cif
_cod_data_source_block           10b
_cod_database_code               4025925
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, 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 0.0000 0.01592(11) 0.2500 0.0390(4) Uani 1 2 d S . .
C2 C 0.0611(11) 0.0734(10) 0.3274(16) 0.034(3) Uani 0.50 1 d P A 1
C3 C 0.03409(7) 0.16523(7) 0.31555(12) 0.0322(3) Uani 1 1 d . . .
H3 H 0.0056 0.1812 0.4159 0.039 Uiso 1 1 calc R A 1
C4 C -0.0589(11) 0.0640(10) 0.1734(18) 0.035(3) Uani 0.50 1 d P . 2
C5 C 0.0000 -0.07893(11) 0.2500 0.0446(4) Uani 1 2 d S . .
C6 C 0.0000 -0.15865(11) 0.2500 0.0410(4) Uani 1 2 d S . .
C7 C 0.0000 -0.25418(10) 0.2500 0.0386(4) Uani 1 2 d S . .
C8 C 0.06884(9) -0.30071(8) 0.30692(16) 0.0519(4) Uani 1 1 d . . .
H8 H 0.1163 -0.2694 0.3462 0.062 Uiso 1 1 calc R A .
C9 C 0.06825(11) -0.39241(10) 0.3064(2) 0.0758(5) Uani 1 1 d . A .
H9 H 0.1155 -0.4241 0.3455 0.091 Uiso 1 1 calc R . .
C10 C 0.0000 -0.43834(14) 0.2500 0.0867(8) Uani 1 2 d S . .
H10 H 0.0000 -0.5016 0.2500 0.104 Uiso 1 2 calc PR A .
C11 C 0.1280(9) 0.0371(11) 0.3983(16) 0.054(3) Uani 0.50 1 d P A 1
H11A H 0.1670 0.0739 0.4522 0.065 Uiso 0.50 1 calc PR A 1
H11B H 0.1365 -0.0254 0.3945 0.065 Uiso 0.50 1 calc PR A 1
C12 C 0.10361(7) 0.23222(7) 0.28832(13) 0.0334(3) Uani 1 1 d . A .
C13 C 0.16568(7) 0.21780(8) 0.17674(15) 0.0447(3) Uani 1 1 d . . .
H13 H 0.1657 0.1639 0.1187 0.054 Uiso 1 1 calc R A .
C14 C 0.22738(8) 0.28060(9) 0.14882(17) 0.0541(4) Uani 1 1 d . A .
H14 H 0.2690 0.2699 0.0712 0.065 Uiso 1 1 calc R . .
C15 C 0.22883(9) 0.35870(9) 0.23317(17) 0.0556(4) Uani 1 1 d . . .
H15 H 0.2714 0.4018 0.2141 0.067 Uiso 1 1 calc R A .
C16 C 0.16838(9) 0.37391(8) 0.34505(17) 0.0524(3) Uani 1 1 d . A .
H16 H 0.1696 0.4274 0.4043 0.063 Uiso 1 1 calc R . .
C17 C 0.10552(8) 0.31142(7) 0.37185(14) 0.0409(3) Uani 1 1 d . . .
H17 H 0.0634 0.3230 0.4481 0.049 Uiso 1 1 calc R A .
C18 C -0.1329(7) 0.0396(10) 0.0769(17) 0.043(2) Uani 0.50 1 d P B 2
H18A H -0.1375 -0.0254 0.0712 0.052 Uiso 0.50 1 calc PR B 2
H18B H -0.1261 0.0639 -0.0286 0.052 Uiso 0.50 1 calc PR B 2
H18C H -0.1841 0.0641 0.1244 0.052 Uiso 0.50 1 calc PR B 2
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
_geom_angle_site_symmetry_3
C4 C1 C5 122.3(6) . .
C4 C1 C2 111.33(19) . .
C5 C1 C2 126.3(6) . .
C11 C2 C3 130.9(13) . .
C11 C2 C1 119.5(13) . .
C3 C2 C1 109.6(10) . .
C2 C3 C12 115.4(7) . .
C2 C3 C3 104.8(6) . 3
C12 C3 C3 113.34(9) . 3
C12 C3 C4 118.0(7) . 3
C3 C3 C4 102.5(6) 3 3
C1 C4 C18 133.4(13) . .
C1 C4 C3 108.3(10) . 3
C18 C4 C3 118.1(11) . 3
C6 C5 C1 180.0 . .
C5 C6 C7 180.0 . .
C8 C7 C8 119.41(16) 3 .
C8 C7 C6 120.29(8) 3 .
C8 C7 C6 120.29(8) . .
C9 C8 C7 119.87(14) . .
C10 C9 C8 120.62(16) . .
C9 C10 C9 119.6(2) . 3
C17 C12 C13 118.16(11) . .
C17 C12 C3 120.48(10) . .
C13 C12 C3 121.33(10) . .
C14 C13 C12 121.04(12) . .
C15 C14 C13 120.21(13) . .
C16 C15 C14 119.65(12) . .
C15 C16 C17 120.28(12) . .
C12 C17 C16 120.66(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C4 1.351(16) .
C1 C5 1.425(2) .
C1 C2 1.459(15) .
C2 C11 1.34(2) .
C2 C3 1.448(15) .
C3 C12 1.5121(15) .
C3 C3 1.559(2) 3
C3 C4 1.574(14) 3
C4 C18 1.48(2) .
C4 C3 1.574(14) 3
C5 C6 1.198(2) .
C6 C7 1.435(2) .
C7 C8 1.3860(15) 3
C7 C8 1.3860(15) .
C8 C9 1.3779(18) .
C9 C10 1.373(2) .
C10 C9 1.373(2) 3
C12 C17 1.3885(15) .
C12 C13 1.3893(16) .
C13 C14 1.3811(17) .
C14 C15 1.3778(19) .
C15 C16 1.375(2) .
C16 C17 1.3895(17) .
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
C4 C1 C2 C11 -174.5(6) . .
C5 C1 C2 C11 4.8(16) . .
C4 C1 C2 C3 7.3(19) . .
C5 C1 C2 C3 -173.3(4) . .
C11 C2 C3 C12 40.6(17) . .
C1 C2 C3 C12 -141.6(7) . .
C11 C2 C3 C3 166.0(14) . 3
C1 C2 C3 C3 -16.2(11) . 3
C11 C2 C3 C4 -159(24) . 3
C1 C2 C3 C4 19(22) . 3
C5 C1 C4 C18 0(2) . .
C2 C1 C4 C18 179.3(8) . .
C5 C1 C4 C3 -174.3(4) . 3
C2 C1 C4 C3 5.1(18) . 3
C4 C1 C5 C6 0(24) . .
C2 C1 C5 C6 0(91) . .
C1 C5 C6 C7 0.0 . .
C5 C6 C7 C8 0(15) . 3
C5 C6 C7 C8 0(96) . .
C8 C7 C8 C9 0.01(11) 3 .
C6 C7 C8 C9 -179.99(11) . .
C7 C8 C9 C10 0.0(2) . .
C8 C9 C10 C9 0.01(12) . 3
C2 C3 C12 C17 -135.6(6) . .
C3 C3 C12 C17 103.49(12) 3 .
C4 C3 C12 C17 -136.7(6) 3 .
C2 C3 C12 C13 46.2(6) . .
C3 C3 C12 C13 -74.63(13) 3 .
C4 C3 C12 C13 45.2(7) 3 .
C17 C12 C13 C14 -0.35(18) . .
C3 C12 C13 C14 177.82(11) . .
C12 C13 C14 C15 0.7(2) . .
C13 C14 C15 C16 -0.2(2) . .
C14 C15 C16 C17 -0.8(2) . .
C13 C12 C17 C16 -0.58(17) . .
C3 C12 C17 C16 -178.76(11) . .
C15 C16 C17 C12 1.14(19) . .
