#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/30/1503020.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_1503020
loop_
_publ_author_name
'Phillips, Eric M.'
'Roberts, John M.'
'Scheidt, Karl A.'
_publ_section_title
;
 Catalytic enantioselective total syntheses of bakkenolides I, J, and S:
 application of a carbene-catalyzed desymmetrization.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2830
_journal_page_last               2833
_journal_paper_doi               10.1021/ol100938j
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C15 H22 O3'
_chemical_formula_weight         250.33
_chemical_name_common
(1'R,2'S,3a'R,4'S,7a'S)-1'-hydroxy-3a',4'-dimethyl-4-methylenedecahydro-2H-spiro[furan-3,2'-inden]-2-one
_chemical_name_systematic        ?
_space_group_IT_number           19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2009-09-11 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.33740(10)
_cell_length_b                   7.47950(10)
_cell_length_c                   25.3435(5)
_cell_measurement_temperature    100(2)
_cell_volume                     1390.85(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0587
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            30953
_diffrn_reflns_theta_full        30.17
_diffrn_reflns_theta_max         30.17
_diffrn_reflns_theta_min         1.61
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9840
_exptl_absorpt_correction_T_min  0.9499
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.142
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         4107
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0544P)²+0.1934P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.0975
_reflns_number_gt                3858
_reflns_number_total             4107
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol100938j_si_001.cif
_cod_data_source_block           n0146_0m
_cod_database_code               1503020
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -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
O1 O -0.12604(11) 0.50846(11) 0.92387(3) 0.02011(16) Uani 1 1 d .
H1 H -0.1700 0.5552 0.9512 0.030 Uiso 1 1 calc R
O2 O 0.30604(13) 0.79428(11) 0.98611(3) 0.02667(19) Uani 1 1 d .
O3 O 0.23589(13) 0.55687(11) 1.03447(3) 0.02428(18) Uani 1 1 d .
C1 C 0.03988(13) 0.59343(14) 0.91106(4) 0.01601(19) Uani 1 1 d .
H1A H 0.0279 0.7247 0.9178 0.019 Uiso 1 1 calc R
C2 C 0.25632(15) 0.64027(15) 0.98805(4) 0.0193(2) Uani 1 1 d .
C3 C 0.08714(14) 0.56354(16) 0.85297(4) 0.0193(2) Uani 1 1 d .
H3 H 0.0734 0.4331 0.8453 0.023 Uiso 1 1 calc R
C4 C 0.31693(15) 0.81676(16) 0.85041(4) 0.0218(2) Uani 1 1 d .
H4 H 0.2774 0.8576 0.8862 0.026 Uiso 1 1 calc R
C5 C 0.37982(18) 0.5268(2) 0.80011(5) 0.0307(3) Uani 1 1 d .
H5A H 0.3477 0.3998 0.7982 0.046 Uiso 1 1 calc R
H5B H 0.5125 0.5392 0.8024 0.046 Uiso 1 1 calc R
H5C H 0.3357 0.5882 0.7684 0.046 Uiso 1 1 calc R
C6 C 0.36701(15) 0.52165(16) 0.89968(4) 0.0223(2) Uani 1 1 d .
H6A H 0.4731 0.5899 0.9130 0.027 Uiso 1 1 calc R
H6B H 0.4070 0.3980 0.8920 0.027 Uiso 1 1 calc R
C7 C 0.21230(14) 0.51988(14) 0.94177(4) 0.0178(2) Uani 1 1 d .
C8 C 0.29148(14) 0.61026(16) 0.84914(4) 0.0206(2) Uani 1 1 d .
C9 C 0.51470(16) 0.8770(2) 0.84364(5) 0.0286(3) Uani 1 1 d .
H9A H 0.5565 0.8470 0.8080 0.043 Uiso 1 1 calc R
H9B H 0.5915 0.8161 0.8697 0.043 Uiso 1 1 calc R
H9C H 0.5228 1.0066 0.8489 0.043 Uiso 1 1 calc R
C10 C -0.03663(16) 0.66599(19) 0.81504(4) 0.0255(2) Uani 1 1 d .
H10A H -0.0125 0.6254 0.7785 0.031 Uiso 1 1 calc R
H10B H -0.1654 0.6384 0.8234 0.031 Uiso 1 1 calc R
C11 C 0.17796(16) 0.34283(15) 0.96841(5) 0.0225(2) Uani 1 1 d .
C12 C 0.16469(19) 0.37706(16) 1.02692(5) 0.0275(2) Uani 1 1 d .
H12A H 0.0365 0.3695 1.0389 0.033 Uiso 1 1 calc R
H12B H 0.2381 0.2889 1.0468 0.033 Uiso 1 1 calc R
C13 C 0.19437(16) 0.91203(19) 0.81052(5) 0.0285(3) Uani 1 1 d .
H13A H 0.2316 0.8774 0.7744 0.034 Uiso 1 1 calc R
H13B H 0.2114 1.0428 0.8140 0.034 Uiso 1 1 calc R
C14 C 0.1597(2) 0.18447(17) 0.94614(6) 0.0345(3) Uani 1 1 d .
H14A H 0.1680 0.1730 0.9089 0.041 Uiso 1 1 calc R
H14B H 0.1382 0.0819 0.9674 0.041 Uiso 1 1 calc R
C15 C -0.00771(17) 0.86720(19) 0.81820(5) 0.0275(3) Uani 1 1 d .
H15A H -0.0490 0.9116 0.8530 0.033 Uiso 1 1 calc R
H15B H -0.0809 0.9273 0.7906 0.033 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
C2 O3 C12 110.78(9)
O1 C1 C3 110.56(8)
O1 C1 C7 114.81(8)
C3 C1 C7 103.96(8)
O2 C2 O3 120.86(10)
O2 C2 C7 126.84(10)
O3 C2 C7 112.30(9)
C10 C3 C1 113.42(9)
C10 C3 C8 115.11(10)
C1 C3 C8 104.35(8)
C13 C4 C9 110.27(10)
C13 C4 C8 112.22(10)
C9 C4 C8 113.83(10)
C8 C6 C7 108.06(8)
C11 C7 C2 102.20(9)
C11 C7 C6 115.84(9)
C2 C7 C6 111.72(9)
C11 C7 C1 113.05(9)
C2 C7 C1 110.16(8)
C6 C7 C1 104.04(8)
C5 C8 C3 111.68(9)
C5 C8 C6 110.21(9)
C3 C8 C6 101.49(9)
C5 C8 C4 111.71(10)
C3 C8 C4 109.89(9)
C6 C8 C4 111.44(9)
C15 C10 C3 112.32(10)
C14 C11 C7 127.90(12)
C14 C11 C12 124.52(12)
C7 C11 C12 107.57(9)
O3 C12 C11 105.26(9)
C4 C13 C15 112.52(10)
C10 C15 C13 110.15(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.4112(13)
O2 C2 1.2093(14)
O3 C2 1.3401(14)
O3 C12 1.4554(15)
C1 C3 1.5290(14)
C1 C7 1.5840(14)
C2 C7 1.5135(15)
C3 C10 1.5283(16)
C3 C8 1.5425(15)
C4 C13 1.5292(16)
C4 C9 1.5291(16)
C4 C8 1.5561(16)
C5 C8 1.5342(15)
C6 C8 1.5451(16)
C6 C7 1.5578(16)
C7 C11 1.5075(16)
C10 C15 1.5219(19)
C11 C14 1.3188(17)
C11 C12 1.5079(17)
C13 C15 1.5326(17)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 10006497 ChemSpider
