#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/49/1504993.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_1504993
loop_
_publ_author_name
'Avetta, Jr, Christopher T'
'Konkol, Leah C.'
'Taylor, Carla N.'
'Dugan, Karen C.'
'Stern, Charlotte L.'
'Thomson, Regan J.'
_publ_section_title
;
 Diastereoselective oxidative carbon-carbon bond formation via silyl
 bis-enol ethers.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              5621
_journal_page_last               5624
_journal_paper_doi               10.1021/ol802516z
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration unk
_chemical_formula_sum            'C14 H20 O2'
_chemical_formula_weight         220.30
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 100.371(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.985(3)
_cell_length_b                   8.644(4)
_cell_length_c                   12.082(6)
_cell_measurement_reflns_used    6321
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.44
_cell_measurement_theta_min      2.91
_cell_volume                     614.8(5)
_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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10610
_diffrn_reflns_theta_full        30.53
_diffrn_reflns_theta_max         30.53
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9949
_exptl_absorpt_correction_T_min  0.9801
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   face-indexed
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.327
_exptl_crystal_size_mid          0.226
_exptl_crystal_size_min          0.076
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.219
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1990
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.219
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0304
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0546P)²+0.0517P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0800
_refine_ls_wR_factor_ref         0.0945
_reflns_number_gt                1906
_reflns_number_total             1990
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol802516z_si_006.cif
_cod_data_source_block           s40y
_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      P2(1)
_cod_database_code               1504993
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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 0.49840(16) 0.20898(13) 0.03434(8) 0.0184(2) Uani 1 1 d .
O2 O 0.72474(18) 0.59142(14) 0.31631(8) 0.0217(2) Uani 1 1 d .
C1 C 0.5493(2) 0.18029(16) 0.13473(11) 0.0146(2) Uani 1 1 d .
C2 C 0.4980(3) 0.02882(18) 0.17860(13) 0.0225(3) Uani 1 1 d .
H2 H 0.4217 -0.0459 0.1277 0.027 Uiso 1 1 calc R
C3 C 0.5543(3) -0.00820(19) 0.28748(13) 0.0224(3) Uani 1 1 d .
H3 H 0.5093 -0.1068 0.3105 0.027 Uiso 1 1 calc R
C4 C 0.6840(2) 0.09581(19) 0.37558(11) 0.0183(3) Uani 1 1 d .
C5 C 0.8096(2) 0.21833(17) 0.31869(11) 0.0159(3) Uani 1 1 d .
H5A H 0.8728 0.2971 0.3752 0.019 Uiso 1 1 calc R
H5B H 0.9385 0.1686 0.2914 0.019 Uiso 1 1 calc R
C6 C 0.6586(2) 0.29892(15) 0.21975(10) 0.0130(2) Uani 1 1 d .
H6 H 0.5329 0.3501 0.2505 0.016 Uiso 1 1 calc R
C7 C 0.5185(3) 0.1698(2) 0.44334(14) 0.0295(4) Uani 1 1 d .
H7A H 0.4092 0.2344 0.3935 0.044 Uiso 1 1 calc R
H7B H 0.6034 0.2339 0.5035 0.044 Uiso 1 1 calc R
H7C H 0.4372 0.0884 0.4763 0.044 Uiso 1 1 calc R
C8 C 0.8587(3) -0.0003(2) 0.45496(13) 0.0264(3) Uani 1 1 d .
H8A H 0.7801 -0.0793 0.4918 0.040 Uiso 1 1 calc R
H8B H 0.9456 0.0674 0.5121 0.040 Uiso 1 1 calc R
H8C H 0.9621 -0.0506 0.4118 0.040 Uiso 1 1 calc R
C9 C 0.7784(2) 0.42548(15) 0.16452(10) 0.0127(2) Uani 1 1 d .
H9 H 0.6744 0.4521 0.0926 0.015 Uiso 1 1 calc R
C10 C 0.8094(2) 0.57317(16) 0.23298(11) 0.0152(2) Uani 1 1 d .
C11 C 0.9433(2) 0.69950(17) 0.18881(12) 0.0192(3) Uani 1 1 d .
H11A H 0.9838 0.7792 0.2479 0.023 Uiso 1 1 calc R
H11B H 0.8467 0.7492 0.1233 0.023 Uiso 1 1 calc R
C12 C 1.1608(2) 0.63987(19) 0.15329(13) 0.0214(3) Uani 1 1 d .
H12A H 1.2303 0.7239 0.1153 0.026 Uiso 1 1 calc R
H12B H 1.2709 0.6089 0.2210 0.026 Uiso 1 1 calc R
C13 C 1.1115(2) 0.50243(18) 0.07429(12) 0.0191(3) Uani 1 1 d .
H13A H 1.2546 0.4650 0.0534 0.023 Uiso 1 1 calc R
H13B H 1.0080 0.5344 0.0047 0.023 Uiso 1 1 calc R
C14 C 1.0027(2) 0.37322(16) 0.13112(12) 0.0173(3) Uani 1 1 d .
H14A H 1.1091 0.3392 0.1992 0.021 Uiso 1 1 calc R
H14B H 0.9733 0.2838 0.0793 0.021 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 0.0000 '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 0.0000 '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
O1 C1 C2 120.63(12)
O1 C1 C6 122.41(13)
C2 C1 C6 116.91(11)
C3 C2 C1 122.52(13)
C3 C2 H2 118.7
C1 C2 H2 118.7
C2 C3 C4 124.19(14)
C2 C3 H3 117.9
C4 C3 H3 117.9
C3 C4 C8 109.11(14)
C3 C4 C5 109.23(11)
C8 C4 C5 108.75(12)
C3 C4 C7 109.14(13)
C8 C4 C7 109.01(12)
C5 C4 C7 111.57(14)
C6 C5 C4 113.37(11)
C6 C5 H5A 108.9
C4 C5 H5A 108.9
C6 C5 H5B 108.9
C4 C5 H5B 108.9
H5A C5 H5B 107.7
C1 C6 C5 110.12(12)
C1 C6 C9 111.63(10)
C5 C6 C9 114.21(11)
C1 C6 H6 106.8
C5 C6 H6 106.8
C9 C6 H6 106.8
C4 C7 H7A 109.5
C4 C7 H7B 109.5
H7A C7 H7B 109.5
C4 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C4 C8 H8A 109.5
C4 C8 H8B 109.5
H8A C8 H8B 109.5
C4 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C10 C9 C6 112.74(10)
C10 C9 C14 111.35(10)
C6 C9 C14 113.91(11)
C10 C9 H9 106.0
C6 C9 H9 106.0
C14 C9 H9 106.0
O2 C10 C11 121.75(13)
O2 C10 C9 122.21(13)
C11 C10 C9 115.98(11)
C10 C11 C12 112.84(12)
C10 C11 H11A 109.0
C12 C11 H11A 109.0
C10 C11 H11B 109.0
C12 C11 H11B 109.0
H11A C11 H11B 107.8
C13 C12 C11 111.11(11)
C13 C12 H12A 109.4
C11 C12 H12A 109.4
C13 C12 H12B 109.4
C11 C12 H12B 109.4
H12A C12 H12B 108.0
C12 C13 C14 110.00(11)
C12 C13 H13A 109.7
C14 C13 H13A 109.7
C12 C13 H13B 109.7
C14 C13 H13B 109.7
H13A C13 H13B 108.2
C13 C14 C9 111.61(11)
C13 C14 H14A 109.3
C9 C14 H14A 109.3
C13 C14 H14B 109.3
C9 C14 H14B 109.3
H14A C14 H14B 108.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2216(17)
O2 C10 1.2163(17)
C1 C2 1.466(2)
C1 C6 1.5144(18)
C2 C3 1.337(2)
C2 H2 0.9500
C3 C4 1.499(2)
C3 H3 0.9500
C4 C8 1.530(2)
C4 C5 1.532(2)
C4 C7 1.533(2)
C5 C6 1.5303(18)
C5 H5A 0.9900
C5 H5B 0.9900
C6 C9 1.5259(18)
C6 H6 1.0000
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 C10 1.5143(19)
C9 C14 1.5376(18)
C9 H9 1.0000
C10 C11 1.5077(19)
C11 C12 1.532(2)
C11 H11A 0.9900
C11 H11B 0.9900
C12 C13 1.519(2)
C12 H12A 0.9900
C12 H12B 0.9900
C13 C14 1.5177(19)
C13 H13A 0.9900
C13 H13B 0.9900
C14 H14A 0.9900
C14 H14B 0.9900
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
O1 C1 C2 C3 178.77(15)
C6 C1 C2 C3 -3.4(2)
C1 C2 C3 C4 -2.9(3)
C2 C3 C4 C8 -138.53(17)
C2 C3 C4 C5 -19.8(2)
C2 C3 C4 C7 102.45(18)
C3 C4 C5 C6 48.90(16)
C8 C4 C5 C6 167.88(12)
C7 C4 C5 C6 -71.85(15)
O1 C1 C6 C5 -150.53(12)
C2 C1 C6 C5 31.72(16)
O1 C1 C6 C9 -22.58(17)
C2 C1 C6 C9 159.67(11)
C4 C5 C6 C1 -55.56(15)
C4 C5 C6 C9 177.93(11)
C1 C6 C9 C10 157.92(10)
C5 C6 C9 C10 -76.35(14)
C1 C6 C9 C14 -73.94(14)
C5 C6 C9 C14 51.79(14)
C6 C9 C10 O2 -7.39(18)
C14 C9 C10 O2 -136.86(13)
C6 C9 C10 C11 175.22(11)
C14 C9 C10 C11 45.75(15)
O2 C10 C11 C12 137.02(14)
C9 C10 C11 C12 -45.57(16)
C10 C11 C12 C13 51.14(16)
C11 C12 C13 C14 -58.53(16)
C12 C13 C14 C9 59.74(15)
C10 C9 C14 C13 -52.45(14)
C6 C9 C14 C13 178.70(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30651532
