#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:19:27 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178430 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/51/4025118.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_4025118
loop_
_publ_author_name
'Liang-Feng Yao'
'Yin Wei'
'Min Shi'
_publ_section_title
;
Silver- and Gold-Catalyzed Intramolecular Rearrangement of Propargylic
Alcohols Tethered with Methylenecyclopropanes: Stereoselective Synthesis of
Allenylcyclobutanols and 1-Vinyl-3-oxabicyclo[3.2.1]octan-8-one Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9466
_journal_page_last               9469
_journal_paper_doi               10.1021/jo902261r
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C27 H24 O2'
_chemical_formula_weight         380.46
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2bc 2ac'
_symmetry_space_group_name_H-M   'P c a b'
_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            8
_cell_length_a                   11.3164(12)
_cell_length_b                   17.6548(19)
_cell_length_c                   20.537(2)
_cell_measurement_reflns_used    2367
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      47.675
_cell_measurement_theta_min      4.587
_cell_volume                     4103.0(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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  0.0681
_diffrn_reflns_av_sigmaI/netI    0.0541
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20449
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82477
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.412
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.0058(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3821
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.1231
_refine_ls_R_factor_gt           0.0777
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1084P)²+0.4630P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1888
_refine_ls_wR_factor_ref         0.2259
_reflns_number_gt                2253
_reflns_number_total             3821
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo902261r_si_001.cif
_cod_data_source_block           cd28455
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      Pcab
_cod_database_code               4025118
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'x+1/2, -y, -z+1/2'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'-x-1/2, 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
O1 O 0.0491(2) 0.32555(14) 0.18402(12) 0.0671(7) Uani 1 1 d . . .
O2 O 0.3126(2) 0.23201(12) 0.26558(10) 0.0527(6) Uani 1 1 d . . .
C1 C 0.0952(3) 0.42621(16) 0.34918(14) 0.0420(7) Uani 1 1 d . . .
C2 C 0.0607(3) 0.36319(16) 0.31867(15) 0.0486(8) Uani 1 1 d . . .
H2 H -0.0205 0.3612 0.3119 0.058 Uiso 1 1 calc R . .
C3 C 0.1239(3) 0.29508(16) 0.29305(15) 0.0421(8) Uani 1 1 d . . .
C4 C 0.0906(3) 0.28092(19) 0.22226(16) 0.0508(8) Uani 1 1 d . . .
C5 C 0.1307(3) 0.20101(19) 0.20924(17) 0.0559(9) Uani 1 1 d . . .
H5 H 0.0953 0.1793 0.1699 0.067 Uiso 1 1 calc R . .
C6 C 0.2662(3) 0.2100(2) 0.20408(17) 0.0575(9) Uani 1 1 d . . .
H6A H 0.3013 0.1624 0.1906 0.069 Uiso 1 1 calc R . .
H6B H 0.2852 0.2480 0.1716 0.069 Uiso 1 1 calc R . .
C7 C 0.2604(3) 0.29933(17) 0.29084(16) 0.0487(8) Uani 1 1 d . . .
H7A H 0.2837 0.3420 0.2640 0.058 Uiso 1 1 calc R . .
H7B H 0.2901 0.3082 0.3345 0.058 Uiso 1 1 calc R . .
C8 C 0.0966(3) 0.15851(18) 0.27110(17) 0.0587(10) Uani 1 1 d . . .
H8A H 0.1579 0.1227 0.2831 0.070 Uiso 1 1 calc R . .
H8B H 0.0233 0.1310 0.2647 0.070 Uiso 1 1 calc R . .
C9 C 0.0816(3) 0.21952(16) 0.32489(16) 0.0478(8) Uani 1 1 d . . .
H9 H -0.0038 0.2251 0.3311 0.057 Uiso 1 1 calc R . .
C10 C 0.1315(3) 0.20256(17) 0.39148(16) 0.0500(8) Uani 1 1 d . . .
C11 C 0.2340(3) 0.1609(2) 0.40042(18) 0.0684(11) Uani 1 1 d . . .
H11 H 0.2756 0.1436 0.3643 0.082 Uiso 1 1 calc R . .
C12 C 0.2751(4) 0.1446(3) 0.4621(2) 0.0907(15) Uani 1 1 d . . .
H12 H 0.3449 0.1175 0.4670 0.109 Uiso 1 1 calc R . .
C13 C 0.2147(5) 0.1679(3) 0.5160(2) 0.0924(15) Uani 1 1 d . . .
H13 H 0.2417 0.1554 0.5574 0.111 Uiso 1 1 calc R . .
C14 C 0.1144(5) 0.2097(2) 0.5085(2) 0.0841(14) Uani 1 1 d . . .
H14 H 0.0737 0.2268 0.5450 0.101 Uiso 1 1 calc R . .
C15 C 0.0721(4) 0.2270(2) 0.44639(18) 0.0666(11) Uani 1 1 d . . .
H15 H 0.0033 0.2553 0.4419 0.080 Uiso 1 1 calc R . .
C16 C 0.0078(3) 0.48589(16) 0.36501(15) 0.0461(8) Uani 1 1 d . . .
C17 C -0.0954(3) 0.49564(19) 0.32905(18) 0.0589(10) Uani 1 1 d . . .
H17 H -0.1077 0.4659 0.2923 0.071 Uiso 1 1 calc R . .
C18 C -0.1806(3) 0.5486(2) 0.34651(19) 0.0680(11) Uani 1 1 d . . .
H18 H -0.2500 0.5530 0.3225 0.082 Uiso 1 1 calc R . .
C19 C -0.1613(4) 0.5945(2) 0.3995(2) 0.0739(12) Uani 1 1 d . . .
H19 H -0.2177 0.6301 0.4117 0.089 Uiso 1 1 calc R . .
C20 C -0.0590(4) 0.5877(2) 0.4344(2) 0.0745(12) Uani 1 1 d . . .
H20 H -0.0457 0.6193 0.4699 0.089 Uiso 1 1 calc R . .
C21 C 0.0250(3) 0.53418(19) 0.41759(17) 0.0583(10) Uani 1 1 d . . .
H21 H 0.0942 0.5305 0.4419 0.070 Uiso 1 1 calc R . .
C22 C 0.2197(3) 0.44129(17) 0.37074(15) 0.0457(8) Uani 1 1 d . . .
C23 C 0.2890(3) 0.49426(19) 0.33892(19) 0.0615(10) Uani 1 1 d . . .
H23 H 0.2583 0.5198 0.3031 0.074 Uiso 1 1 calc R . .
C24 C 0.4022(4) 0.5100(2) 0.3591(2) 0.0775(12) Uani 1 1 d . . .
H24 H 0.4478 0.5449 0.3364 0.093 Uiso 1 1 calc R . .
C25 C 0.4474(4) 0.4745(3) 0.4124(2) 0.0788(13) Uani 1 1 d . . .
H25 H 0.5241 0.4849 0.4260 0.095 Uiso 1 1 calc R . .
C26 C 0.3799(4) 0.4236(2) 0.4456(2) 0.0744(12) Uani 1 1 d . . .
H26 H 0.4104 0.4001 0.4825 0.089 Uiso 1 1 calc R . .
C27 C 0.2666(3) 0.4063(2) 0.42528(16) 0.0576(9) Uani 1 1 d . . .
H27 H 0.2218 0.3712 0.4482 0.069 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
_geom_angle_publ_flag
C6 O2 C7 113.4(2) . . ?
C2 C1 C16 120.0(3) . . ?
C2 C1 C22 124.1(3) . . ?
C16 C1 C22 115.9(3) . . ?
C1 C2 C3 134.1(3) . . ?
C1 C2 H2 113.0 . . ?
C3 C2 H2 113.0 . . ?
C2 C3 C4 110.5(3) . . ?
C2 C3 C7 116.7(3) . . ?
C4 C3 C7 103.1(3) . . ?
C2 C3 C9 113.2(3) . . ?
C4 C3 C9 100.6(2) . . ?
C7 C3 C9 111.1(2) . . ?
O1 C4 C5 127.8(3) . . ?
O1 C4 C3 127.6(3) . . ?
C5 C4 C3 104.4(3) . . ?
C4 C5 C8 103.7(3) . . ?
C4 C5 C6 102.5(3) . . ?
C8 C5 C6 111.0(3) . . ?
C4 C5 H5 112.9 . . ?
C8 C5 H5 112.9 . . ?
C6 C5 H5 112.9 . . ?
O2 C6 C5 109.5(3) . . ?
O2 C6 H6A 109.8 . . ?
C5 C6 H6A 109.8 . . ?
O2 C6 H6B 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
O2 C7 C3 112.6(3) . . ?
O2 C7 H7A 109.1 . . ?
C3 C7 H7A 109.1 . . ?
O2 C7 H7B 109.1 . . ?
C3 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C5 C8 C9 106.2(3) . . ?
C5 C8 H8A 110.5 . . ?
C9 C8 H8A 110.5 . . ?
C5 C8 H8B 110.5 . . ?
C9 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
C10 C9 C8 117.8(3) . . ?
C10 C9 C3 115.7(3) . . ?
C8 C9 C3 105.2(3) . . ?
C10 C9 H9 105.7 . . ?
C8 C9 H9 105.7 . . ?
C3 C9 H9 105.7 . . ?
C15 C10 C11 117.7(3) . . ?
C15 C10 C9 119.7(3) . . ?
C11 C10 C9 122.6(3) . . ?
C12 C11 C10 120.9(4) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C13 C12 C11 120.9(4) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 119.3(4) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 120.4(4) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C10 C15 C14 120.7(4) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C21 C16 C17 117.0(3) . . ?
C21 C16 C1 120.8(3) . . ?
C17 C16 C1 122.1(3) . . ?
C18 C17 C16 121.9(3) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C19 C18 C17 119.4(4) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C20 C19 C18 119.9(4) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 120.8(4) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C20 C21 C16 121.1(4) . . ?
C20 C21 H21 119.5 . . ?
C16 C21 H21 119.5 . . ?
C23 C22 C27 117.8(3) . . ?
C23 C22 C1 120.8(3) . . ?
C27 C22 C1 121.3(3) . . ?
C24 C23 C22 121.5(4) . . ?
C24 C23 H23 119.3 . . ?
C22 C23 H23 119.3 . . ?
C25 C24 C23 120.0(4) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 119.7(4) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C25 C26 C27 120.9(4) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 H26 119.6 . . ?
C26 C27 C22 120.1(4) . . ?
C26 C27 H27 119.9 . . ?
C22 C27 H27 119.9 . . ?
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
O1 C4 1.207(4) . ?
O2 C6 1.423(4) . ?
O2 C7 1.425(3) . ?
C1 C2 1.335(4) . ?
C1 C16 1.481(4) . ?
C1 C22 1.501(4) . ?
C2 C3 1.495(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.523(4) . ?
C3 C7 1.547(4) . ?
C3 C9 1.561(4) . ?
C4 C5 1.506(5) . ?
C5 C8 1.525(5) . ?
C5 C6 1.544(5) . ?
C5 H5 0.9800 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.552(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.510(4) . ?
C9 H9 0.9800 . ?
C10 C15 1.382(5) . ?
C10 C11 1.386(5) . ?
C11 C12 1.380(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.364(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.362(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.397(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C21 1.390(4) . ?
C16 C17 1.392(5) . ?
C17 C18 1.390(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.366(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.384(5) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.384(4) . ?
C22 C27 1.385(4) . ?
C23 C24 1.374(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.361(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.364(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.382(5) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
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
C16 C1 C2 C3 176.5(3) . . . . ?
C22 C1 C2 C3 -4.8(6) . . . . ?
C1 C2 C3 C4 -128.0(4) . . . . ?
C1 C2 C3 C7 -10.7(5) . . . . ?
C1 C2 C3 C9 120.1(4) . . . . ?
C2 C3 C4 O1 20.5(5) . . . . ?
C7 C3 C4 O1 -104.9(4) . . . . ?
C9 C3 C4 O1 140.2(4) . . . . ?
C2 C3 C4 C5 -164.3(3) . . . . ?
C7 C3 C4 C5 70.3(3) . . . . ?
C9 C3 C4 C5 -44.5(3) . . . . ?
O1 C4 C5 C8 -143.8(4) . . . . ?
C3 C4 C5 C8 41.0(3) . . . . ?
O1 C4 C5 C6 100.6(4) . . . . ?
C3 C4 C5 C6 -74.6(3) . . . . ?
C7 O2 C6 C5 -55.9(4) . . . . ?
C4 C5 C6 O2 66.0(3) . . . . ?
C8 C5 C6 O2 -44.2(4) . . . . ?
C6 O2 C7 C3 53.0(4) . . . . ?
C2 C3 C7 O2 -179.8(3) . . . . ?
C4 C3 C7 O2 -58.6(3) . . . . ?
C9 C3 C7 O2 48.4(3) . . . . ?
C4 C5 C8 C9 -20.2(3) . . . . ?
C6 C5 C8 C9 89.1(3) . . . . ?
C5 C8 C9 C10 -137.6(3) . . . . ?
C5 C8 C9 C3 -7.0(3) . . . . ?
C2 C3 C9 C10 -79.5(4) . . . . ?
C4 C3 C9 C10 162.7(3) . . . . ?
C7 C3 C9 C10 54.0(4) . . . . ?
C2 C3 C9 C8 148.7(3) . . . . ?
C4 C3 C9 C8 30.9(3) . . . . ?
C7 C3 C9 C8 -77.8(3) . . . . ?
C8 C9 C10 C15 -143.8(3) . . . . ?
C3 C9 C10 C15 90.7(4) . . . . ?
C8 C9 C10 C11 34.1(5) . . . . ?
C3 C9 C10 C11 -91.4(4) . . . . ?
C15 C10 C11 C12 -0.2(6) . . . . ?
C9 C10 C11 C12 -178.1(4) . . . . ?
C10 C11 C12 C13 1.3(7) . . . . ?
C11 C12 C13 C14 -2.0(8) . . . . ?
C12 C13 C14 C15 1.5(7) . . . . ?
C11 C10 C15 C14 -0.3(6) . . . . ?
C9 C10 C15 C14 177.7(3) . . . . ?
C13 C14 C15 C10 -0.4(6) . . . . ?
C2 C1 C16 C21 152.7(3) . . . . ?
C22 C1 C16 C21 -26.1(4) . . . . ?
C2 C1 C16 C17 -26.3(5) . . . . ?
C22 C1 C16 C17 154.9(3) . . . . ?
C21 C16 C17 C18 -3.1(5) . . . . ?
C1 C16 C17 C18 176.0(3) . . . . ?
C16 C17 C18 C19 2.1(6) . . . . ?
C17 C18 C19 C20 0.0(6) . . . . ?
C18 C19 C20 C21 -0.9(6) . . . . ?
C19 C20 C21 C16 -0.2(6) . . . . ?
C17 C16 C21 C20 2.2(5) . . . . ?
C1 C16 C21 C20 -176.9(3) . . . . ?
C2 C1 C22 C23 108.0(4) . . . . ?
C16 C1 C22 C23 -73.3(4) . . . . ?
C2 C1 C22 C27 -76.0(4) . . . . ?
C16 C1 C22 C27 102.7(3) . . . . ?
C27 C22 C23 C24 2.2(5) . . . . ?
C1 C22 C23 C24 178.4(3) . . . . ?
C22 C23 C24 C25 -1.5(6) . . . . ?
C23 C24 C25 C26 -0.3(6) . . . . ?
C24 C25 C26 C27 1.3(6) . . . . ?
C25 C26 C27 C22 -0.6(6) . . . . ?
C23 C22 C27 C26 -1.2(5) . . . . ?
C1 C22 C27 C26 -177.3(3) . . . . ?
