#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/22/1502243.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_1502243
loop_
_publ_author_name
'Wu, Yen-Ku'
'McDonald, Robert'
'West, F. G.'
_publ_section_title
;
 Homologous Mukaiyama reactions via trapping of the Nazarov intermediate
 with silyloxyalkenes.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3584
_journal_page_last               3587
_journal_paper_doi               10.1021/ol201125h
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C22 H24 O3'
_chemical_formula_sum            'C22 H24 O3'
_chemical_formula_weight         336.41
_chemical_name_systematic
'methyl (1,3-dimethyl-2-oxo-4,5-diphenylcyclopentyl)acetate'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 98.5362(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6158(5)
_cell_length_b                   10.8562(4)
_cell_length_c                   14.9637(6)
_cell_measurement_reflns_used    7875
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.35
_cell_measurement_theta_min      2.33
_cell_volume                     1866.07(13)
_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    'SHELXD (Schneider & Sheldrick, 2002)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0158
_diffrn_reflns_av_sigmaI/netI    0.0128
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16238
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9827
_exptl_absorpt_correction_T_min  0.9696
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4289
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0371
_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)+(0.0472P)²+0.4804P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1012
_reflns_number_gt                3783
_reflns_number_total             4289
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ol201125h_si_002.cif
_cod_data_source_block           3a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1502243
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.25613(7) 0.04181(9) 0.19372(6) 0.0451(2) Uani 1 1 d .
O2 O -0.00713(9) -0.07088(8) 0.19984(6) 0.0474(2) Uani 1 1 d .
O3 O -0.14948(7) -0.02440(8) 0.08681(5) 0.03482(19) Uani 1 1 d .
C1 C 0.08823(8) 0.17732(9) 0.17318(7) 0.0250(2) Uani 1 1 d .
C2 C 0.18887(9) 0.10572(10) 0.22742(7) 0.0291(2) Uani 1 1 d .
C3 C 0.19417(9) 0.13180(10) 0.32763(7) 0.0273(2) Uani 1 1 d .
H3 H 0.1597 0.0593 0.3554 0.033 Uiso 1 1 calc R
C4 C 0.11092(8) 0.24180(9) 0.33123(6) 0.0227(2) Uani 1 1 d .
H4 H 0.1545 0.3192 0.3224 0.027 Uiso 1 1 calc R
C5 C 0.01737(8) 0.22250(9) 0.24730(6) 0.0222(2) Uani 1 1 d .
H5 H -0.0327 0.1522 0.2612 0.027 Uiso 1 1 calc R
C6 C 0.01876(10) 0.09768(10) 0.09985(7) 0.0293(2) Uani 1 1 d .
H6A H -0.0388 0.1504 0.0622 0.035 Uiso 1 1 calc R
H6B H 0.0726 0.0644 0.0604 0.035 Uiso 1 1 calc R
C7 C -0.04442(10) -0.00799(10) 0.13605(7) 0.0297(2) Uani 1 1 d .
C8 C -0.21690(13) -0.12695(13) 0.11211(10) 0.0489(3) Uani 1 1 d .
H8A H -0.2894 -0.1335 0.0696 0.059 Uiso 1 1 calc R
H8B H -0.2350 -0.1139 0.1733 0.059 Uiso 1 1 calc R
H8C H -0.1720 -0.2031 0.1106 0.059 Uiso 1 1 calc R
C9 C 0.14454(10) 0.28388(11) 0.12722(8) 0.0335(2) Uani 1 1 d .
H9A H 0.1896 0.3357 0.1734 0.040 Uiso 1 1 calc R
H9B H 0.0836 0.3335 0.0918 0.040 Uiso 1 1 calc R
H9C H 0.1963 0.2503 0.0872 0.040 Uiso 1 1 calc R
C10 C 0.31651(10) 0.15094(13) 0.37816(8) 0.0411(3) Uani 1 1 d .
H10A H 0.3126 0.1664 0.4422 0.049 Uiso 1 1 calc R
H10B H 0.3525 0.2217 0.3525 0.049 Uiso 1 1 calc R
H10C H 0.3633 0.0770 0.3724 0.049 Uiso 1 1 calc R
C11 C 0.06271(8) 0.25203(9) 0.41927(6) 0.0233(2) Uani 1 1 d .
C12 C -0.01125(9) 0.16240(10) 0.44568(7) 0.0273(2) Uani 1 1 d .
H12 H -0.0315 0.0931 0.4078 0.033 Uiso 1 1 calc R
C13 C -0.05585(9) 0.17293(11) 0.52658(7) 0.0335(2) Uani 1 1 d .
H13 H -0.1071 0.1117 0.5432 0.040 Uiso 1 1 calc R
C14 C -0.02560(10) 0.27254(12) 0.58299(8) 0.0380(3) Uani 1 1 d .
H14 H -0.0561 0.2800 0.6382 0.046 Uiso 1 1 calc R
C15 C 0.04920(12) 0.36094(12) 0.55848(8) 0.0394(3) Uani 1 1 d .
H15 H 0.0710 0.4288 0.5974 0.047 Uiso 1 1 calc R
C16 C 0.09285(10) 0.35128(10) 0.47708(7) 0.0313(2) Uani 1 1 d .
H16 H 0.1438 0.4130 0.4607 0.038 Uiso 1 1 calc R
C17 C -0.06285(8) 0.32978(9) 0.21874(6) 0.0227(2) Uani 1 1 d .
C18 C -0.17317(9) 0.30691(10) 0.17002(7) 0.0304(2) Uani 1 1 d .
H18 H -0.1980 0.2243 0.1584 0.036 Uiso 1 1 calc R
C19 C -0.24672(10) 0.40300(12) 0.13849(9) 0.0387(3) Uani 1 1 d .
H19 H -0.3209 0.3860 0.1048 0.046 Uiso 1 1 calc R
C20 C -0.21222(10) 0.52379(11) 0.15604(9) 0.0383(3) Uani 1 1 d .
H20 H -0.2626 0.5897 0.1346 0.046 Uiso 1 1 calc R
C21 C -0.10399(10) 0.54785(10) 0.20497(8) 0.0335(2) Uani 1 1 d .
H21 H -0.0802 0.6306 0.2174 0.040 Uiso 1 1 calc R
C22 C -0.02984(9) 0.45186(10) 0.23606(7) 0.0271(2) Uani 1 1 d .
H22 H 0.0443 0.4696 0.2696 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
C7 O3 C8 116.32(10)
C6 C1 C2 111.90(9)
C6 C1 C9 108.54(8)
C2 C1 C9 106.04(8)
C6 C1 C5 114.27(8)
C2 C1 C5 103.01(8)
C9 C1 C5 112.72(8)
O1 C2 C3 125.78(10)
O1 C2 C1 124.02(10)
C3 C2 C1 110.15(8)
C2 C3 C10 114.47(9)
C2 C3 C4 104.19(8)
C10 C3 C4 114.90(9)
C11 C4 C3 113.76(8)
C11 C4 C5 114.28(8)
C3 C4 C5 103.60(8)
C17 C5 C4 116.98(8)
C17 C5 C1 114.22(8)
C4 C5 C1 103.83(7)
C7 C6 C1 113.97(9)
O2 C7 O3 123.57(11)
O2 C7 C6 125.56(10)
O3 C7 C6 110.87(9)
C16 C11 C12 118.20(9)
C16 C11 C4 120.46(9)
C12 C11 C4 121.34(9)
C13 C12 C11 120.97(10)
C14 C13 C12 120.08(11)
C15 C14 C13 119.60(10)
C14 C15 C16 120.39(11)
C15 C16 C11 120.74(11)
C22 C17 C18 118.11(9)
C22 C17 C5 122.60(8)
C18 C17 C5 119.25(9)
C19 C18 C17 120.96(10)
C20 C19 C18 120.11(10)
C21 C20 C19 119.62(10)
C20 C21 C22 120.40(10)
C21 C22 C17 120.80(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.2095(13)
O2 C7 1.2010(14)
O3 C7 1.3405(13)
O3 C8 1.4436(15)
C1 C6 1.5296(14)
C1 C2 1.5323(14)
C1 C9 1.5403(15)
C1 C5 1.5555(13)
C2 C3 1.5183(15)
C3 C10 1.5216(15)
C3 C4 1.5426(13)
C4 C11 1.5102(13)
C4 C5 1.5481(13)
C5 C17 1.5129(13)
C6 C7 1.5054(15)
C11 C16 1.3935(14)
C11 C12 1.3935(14)
C12 C13 1.3904(15)
C13 C14 1.3847(18)
C14 C15 1.3801(19)
C15 C16 1.3911(16)
C17 C22 1.3932(14)
C17 C18 1.3993(13)
C18 C19 1.3860(16)
C19 C20 1.3848(18)
C20 C21 1.3826(16)
C21 C22 1.3876(15)
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
C6 C1 C2 O1 46.72(15)
C9 C1 C2 O1 -71.46(13)
C5 C1 C2 O1 169.92(11)
C6 C1 C2 C3 -135.86(9)
C9 C1 C2 C3 105.96(10)
C5 C1 C2 C3 -12.66(11)
O1 C2 C3 C10 39.46(16)
C1 C2 C3 C10 -137.90(10)
O1 C2 C3 C4 165.77(11)
C1 C2 C3 C4 -11.59(11)
C2 C3 C4 C11 156.01(8)
C10 C3 C4 C11 -77.95(12)
C2 C3 C4 C5 31.35(10)
C10 C3 C4 C5 157.39(9)
C11 C4 C5 C17 69.14(11)
C3 C4 C5 C17 -166.54(8)
C11 C4 C5 C1 -164.03(8)
C3 C4 C5 C1 -39.71(9)
C6 C1 C5 C17 -77.97(11)
C2 C1 C5 C17 160.43(8)
C9 C1 C5 C17 46.58(11)
C6 C1 C5 C4 153.49(9)
C2 C1 C5 C4 31.89(10)
C9 C1 C5 C4 -81.96(10)
C2 C1 C6 C7 65.30(11)
C9 C1 C6 C7 -178.02(9)
C5 C1 C6 C7 -51.28(12)
C8 O3 C7 O2 -2.28(16)
C8 O3 C7 C6 177.22(10)
C1 C6 C7 O2 -39.36(16)
C1 C6 C7 O3 141.15(9)
C3 C4 C11 C16 113.53(10)
C5 C4 C11 C16 -127.76(10)
C3 C4 C11 C12 -65.51(12)
C5 C4 C11 C12 53.21(12)
C16 C11 C12 C13 1.36(15)
C4 C11 C12 C13 -179.58(9)
C11 C12 C13 C14 -0.99(16)
C12 C13 C14 C15 -0.16(17)
C13 C14 C15 C16 0.89(18)
C14 C15 C16 C11 -0.50(18)
C12 C11 C16 C15 -0.62(15)
C4 C11 C16 C15 -179.68(10)
C4 C5 C17 C22 27.71(13)
C1 C5 C17 C22 -93.83(11)
C4 C5 C17 C18 -154.75(9)
C1 C5 C17 C18 83.70(11)
C22 C17 C18 C19 1.13(16)
C5 C17 C18 C19 -176.52(10)
C17 C18 C19 C20 -0.89(19)
C18 C19 C20 C21 0.2(2)
C19 C20 C21 C22 0.32(19)
C20 C21 C22 C17 -0.06(17)
C18 C17 C22 C21 -0.65(15)
C5 C17 C22 C21 176.91(10)
