#------------------------------------------------------------------------------
#$Date: 2018-09-12 13:44:06 +0300 (Wed, 12 Sep 2018) $
#$Revision: 210879 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/18/4101891.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_4101891
loop_
_publ_author_name
'Zheng, Huaiji'
'Zheng, Jiyue'
'Yu, Binxun'
'Chen, Qiang'
'Wang, Xiaolei'
'He, Yongping'
'Yang, Zhen'
'She, Xuegong'
_publ_section_title
;
 Pt-Catalyzed Tandem 1,2-Acyloxy Migration/Intramolecular [3 + 2]
 Cycloaddition of Enynyl Esters
;
_journal_coden_ASTM              JACSAT
_journal_issue                   6
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1788
_journal_page_last               1789
_journal_paper_doi               10.1021/ja910346m
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C19 H24 O4'
_chemical_formula_weight         316.38
_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_method           SHELXL-97
_cell_angle_alpha                91.863(2)
_cell_angle_beta                 101.511(2)
_cell_angle_gamma                100.929(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2627(4)
_cell_length_b                   9.2103(4)
_cell_length_c                   11.3983(4)
_cell_measurement_reflns_used    1499
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.46
_cell_measurement_theta_min      2.80
_cell_volume                     832.34(6)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.987
_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_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0141
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4694
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9768
_exptl_absorpt_correction_T_min  0.9659
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       0.050(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3226
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0446
_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)+(0.0480P)²+0.1729P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1239
_reflns_number_gt                2235
_reflns_number_total             3226
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja910346m_si_003.cif
_cod_data_source_block           p-1
_cod_database_code               4101891
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3126(3) 0.8548(2) -0.11529(17) 0.0630(5) Uani 1 1 d . . .
H1 H 0.3527 0.7676 -0.1212 0.076 Uiso 1 1 calc R . .
C2 C 0.2908(3) 0.9384(2) -0.21302(18) 0.0734(6) Uani 1 1 d . . .
H2 H 0.3183 0.9085 -0.2840 0.088 Uiso 1 1 calc R . .
C3 C 0.2291(3) 1.0651(2) -0.20613(19) 0.0714(6) Uani 1 1 d . . .
H3A H 0.2132 1.1206 -0.2727 0.086 Uiso 1 1 calc R . .
C4 C 0.1908(3) 1.1104(2) -0.1014(2) 0.0703(6) Uani 1 1 d . . .
H4 H 0.1489 1.1968 -0.0968 0.084 Uiso 1 1 calc R . .
C5 C 0.2142(2) 1.0283(2) -0.00265(17) 0.0593(5) Uani 1 1 d . . .
H5 H 0.1886 1.0600 0.0685 0.071 Uiso 1 1 calc R . .
C6 C 0.2755(2) 0.89909(18) -0.00856(15) 0.0493(4) Uani 1 1 d . . .
C7 C 0.3011(2) 0.8146(2) 0.10107(16) 0.0536(4) Uani 1 1 d . . .
C8 C 0.3654(2) 0.67315(19) 0.09359(15) 0.0517(4) Uani 1 1 d . . .
H8A H 0.4738 0.6959 0.0706 0.062 Uiso 1 1 calc R . .
H8B H 0.2886 0.6068 0.0301 0.062 Uiso 1 1 calc R . .
C9 C 0.3862(2) 0.59086(19) 0.20849(14) 0.0481(4) Uani 1 1 d . . .
H9 H 0.4134 0.6635 0.2778 0.058 Uiso 1 1 calc R . .
C10 C 0.5319(2) 0.5104(2) 0.21301(18) 0.0649(5) Uani 1 1 d . . .
H10A H 0.5068 0.4402 0.1434 0.078 Uiso 1 1 calc R . .
H10B H 0.6329 0.5819 0.2089 0.078 Uiso 1 1 calc R . .
C11 C 0.4219(3) 0.3210(2) 0.32465(15) 0.0587(5) Uani 1 1 d . . .
H11 H 0.3982 0.2505 0.2542 0.070 Uiso 1 1 calc R . .
C12 C 0.4673(3) 0.2407(2) 0.43678(17) 0.0763(7) Uani 1 1 d . . .
H12A H 0.4979 0.3111 0.5066 0.092 Uiso 1 1 calc R . .
H12B H 0.5640 0.1969 0.4323 0.092 Uiso 1 1 calc R . .
C13 C 0.3207(4) 0.1203(3) 0.4505(2) 0.0969(9) Uani 1 1 d . . .
H13A H 0.3505 0.0741 0.5249 0.116 Uiso 1 1 calc R . .
H13B H 0.2974 0.0447 0.3848 0.116 Uiso 1 1 calc R . .
C14 C 0.1641(4) 0.1837(3) 0.4511(2) 0.0985(8) Uani 1 1 d . . .
H14A H 0.1834 0.2514 0.5217 0.118 Uiso 1 1 calc R . .
H14B H 0.0704 0.1039 0.4550 0.118 Uiso 1 1 calc R . .
C15 C 0.1194(3) 0.2656(2) 0.3388(2) 0.0789(6) Uani 1 1 d . . .
H15A H 0.0895 0.1959 0.2686 0.095 Uiso 1 1 calc R . .
H15B H 0.0226 0.3093 0.3431 0.095 Uiso 1 1 calc R . .
C16 C 0.2672(2) 0.38651(19) 0.32685(14) 0.0525(4) Uani 1 1 d . . .
H16 H 0.2934 0.4554 0.3985 0.063 Uiso 1 1 calc R . .
C17 C 0.2268(2) 0.47630(18) 0.21680(13) 0.0467(4) Uani 1 1 d . . .
C18 C 0.0802(2) 0.5535(2) 0.22368(16) 0.0562(5) Uani 1 1 d . . .
C19 C 0.0765(3) 0.6384(3) 0.33679(18) 0.0765(6) Uani 1 1 d . . .
H19A H 0.0177 0.7177 0.3175 0.115 Uiso 1 1 calc R . .
H19B H 0.1898 0.6785 0.3790 0.115 Uiso 1 1 calc R . .
H19C H 0.0198 0.5734 0.3865 0.115 Uiso 1 1 calc R . .
O1 O 0.2716(2) 0.86008(16) 0.19367(13) 0.0844(5) Uani 1 1 d . . .
O2 O 0.56359(17) 0.43358(16) 0.31871(12) 0.0698(4) Uani 1 1 d . . .
O3 O 0.18187(17) 0.37591(13) 0.11344(10) 0.0601(4) Uani 1 1 d . . .
H3 H 0.1052 0.3996 0.0653 0.090 Uiso 1 1 calc R . .
O4 O -0.03208(17) 0.54453(18) 0.13569(12) 0.0786(5) Uani 1 1 d . . .
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
_geom_angle_publ_flag
C2 C1 C6 120.60(18) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C3 C2 C1 120.27(19) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 119.98(18) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C3 C4 C5 120.14(19) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.53(18) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.48(16) . . ?
C1 C6 C7 122.73(16) . . ?
C5 C6 C7 118.78(16) . . ?
O1 C7 C6 120.40(16) . . ?
O1 C7 C8 121.07(16) . . ?
C6 C7 C8 118.53(15) . . ?
C7 C8 C9 115.84(14) . . ?
C7 C8 H8A 108.3 . . ?
C9 C8 H8A 108.3 . . ?
C7 C8 H8B 108.3 . . ?
C9 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
C10 C9 C8 108.75(14) . . ?
C10 C9 C17 108.56(14) . . ?
C8 C9 C17 113.19(13) . . ?
C10 C9 H9 108.8 . . ?
C8 C9 H9 108.8 . . ?
C17 C9 H9 108.8 . . ?
O2 C10 C9 112.78(15) . . ?
O2 C10 H10A 109.0 . . ?
C9 C10 H10A 109.0 . . ?
O2 C10 H10B 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
O2 C11 C12 107.88(16) . . ?
O2 C11 C16 111.11(14) . . ?
C12 C11 C16 110.77(16) . . ?
O2 C11 H11 109.0 . . ?
C12 C11 H11 109.0 . . ?
C16 C11 H11 109.0 . . ?
C11 C12 C13 110.96(19) . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C12 C13 C14 110.93(19) . . ?
C12 C13 H13A 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C15 110.97(19) . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 C14 110.72(19) . . ?
C16 C15 H15A 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C11 C16 C15 110.31(16) . . ?
C11 C16 C17 110.99(14) . . ?
C15 C16 C17 112.88(15) . . ?
C11 C16 H16 107.5 . . ?
C15 C16 H16 107.5 . . ?
C17 C16 H16 107.5 . . ?
O3 C17 C18 109.17(13) . . ?
O3 C17 C16 107.59(13) . . ?
C18 C17 C16 111.32(13) . . ?
O3 C17 C9 108.89(13) . . ?
C18 C17 C9 110.61(14) . . ?
C16 C17 C9 109.18(13) . . ?
O4 C18 C19 120.94(18) . . ?
O4 C18 C17 118.64(17) . . ?
C19 C18 C17 120.42(16) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C10 O2 C11 110.96(14) . . ?
C17 O3 H3 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.377(3) . ?
C1 C6 1.380(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.365(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.379(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.494(2) . ?
C7 O1 1.209(2) . ?
C7 C8 1.503(2) . ?
C8 C9 1.531(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.522(2) . ?
C9 C17 1.544(2) . ?
C9 H9 0.9800 . ?
C10 O2 1.422(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O2 1.423(2) . ?
C11 C12 1.515(2) . ?
C11 C16 1.518(3) . ?
C11 H11 0.9800 . ?
C12 C13 1.516(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.518(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.524(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.520(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.541(2) . ?
C16 H16 0.9800 . ?
C17 O3 1.4161(19) . ?
C17 C18 1.530(2) . ?
C18 O4 1.211(2) . ?
C18 C19 1.494(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
O3 H3 0.8200 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.2(3) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
C2 C1 C6 C7 -178.34(19) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C4 C5 C6 C7 179.18(17) . . . . ?
C1 C6 C7 O1 177.73(19) . . . . ?
C5 C6 C7 O1 -1.3(3) . . . . ?
C1 C6 C7 C8 -1.8(3) . . . . ?
C5 C6 C7 C8 179.16(16) . . . . ?
O1 C7 C8 C9 1.4(3) . . . . ?
C6 C7 C8 C9 -179.06(15) . . . . ?
C7 C8 C9 C10 -148.73(16) . . . . ?
C7 C8 C9 C17 90.53(19) . . . . ?
C8 C9 C10 O2 178.48(16) . . . . ?
C17 C9 C10 O2 -58.0(2) . . . . ?
O2 C11 C12 C13 179.01(17) . . . . ?
C16 C11 C12 C13 57.2(2) . . . . ?
C11 C12 C13 C14 -56.1(2) . . . . ?
C12 C13 C14 C15 55.6(3) . . . . ?
C13 C14 C15 C16 -56.3(3) . . . . ?
O2 C11 C16 C15 -177.47(14) . . . . ?
C12 C11 C16 C15 -57.6(2) . . . . ?
O2 C11 C16 C17 56.65(18) . . . . ?
C12 C11 C16 C17 176.55(15) . . . . ?
C14 C15 C16 C11 57.1(2) . . . . ?
C14 C15 C16 C17 -178.13(18) . . . . ?
C11 C16 C17 O3 65.23(18) . . . . ?
C15 C16 C17 O3 -59.2(2) . . . . ?
C11 C16 C17 C18 -175.20(15) . . . . ?
C15 C16 C17 C18 60.4(2) . . . . ?
C11 C16 C17 C9 -52.80(18) . . . . ?
C15 C16 C17 C9 -177.23(16) . . . . ?
C10 C9 C17 O3 -64.97(16) . . . . ?
C8 C9 C17 O3 55.87(17) . . . . ?
C10 C9 C17 C18 175.06(14) . . . . ?
C8 C9 C17 C18 -64.09(18) . . . . ?
C10 C9 C17 C16 52.23(17) . . . . ?
C8 C9 C17 C16 173.08(14) . . . . ?
O3 C17 C18 O4 -14.3(2) . . . . ?
C16 C17 C18 O4 -132.89(17) . . . . ?
C9 C17 C18 O4 105.53(19) . . . . ?
O3 C17 C18 C19 165.90(16) . . . . ?
C16 C17 C18 C19 47.3(2) . . . . ?
C9 C17 C18 C19 -74.3(2) . . . . ?
C9 C10 O2 C11 62.3(2) . . . . ?
C12 C11 O2 C10 177.98(15) . . . . ?
C16 C11 O2 C10 -60.42(19) . . . . ?
