#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:45:11 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178822 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/76/4107660.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_4107660
loop_
_publ_author_name
'Petteri Elsner'
'Luca Bernardi'
'Giorgio Dela Salla'
'Jacob Overgaard'
'Karl Anker Jørgensen'
_publ_contact_author             'Overgaard, Jacob'
_publ_contact_author_email       jacobo@chem.au.dk
_publ_section_title
;
 Organocatalytic Asymmetric Conjugate Addition to Allenic Esters and
 Ketones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4897
_journal_page_last               4905
_journal_paper_doi               10.1021/ja710689c
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration rm
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C15 H22 O4'
_chemical_formula_sum            'C15 H22 O4'
_chemical_formula_weight         266.33
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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_date             2007-08-20T11:10:39-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 94.280(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.4832(4)
_cell_length_b                   10.6951(7)
_cell_length_c                   10.6979(5)
_cell_measurement_reflns_used    3722
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.98
_cell_measurement_theta_min      2.69
_cell_measurement_wavelength     0.71073
_cell_volume                     739.71(8)
_computing_cell_refinement       'Saint+ (Bruker-Nonius, 2006)'
_computing_data_collection       'Apex2 (Bruker-Nonius, 2006)'
_computing_data_reduction        'Saint+ (Bruker-Nonius, 2006)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 0.0833
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker X8 APEX-II diffractometer'
_diffrn_measurement_method       'φ-scans and ω-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9362
_diffrn_reflns_theta_full        23.22
_diffrn_reflns_theta_max         23.22
_diffrn_reflns_theta_min         1.91
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         1086
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.08
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0245
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0345P)²+0.0806P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0586
_refine_ls_wR_factor_ref         0.06
_reflns_number_gt                1020
_reflns_number_total             1086
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja710689c-file003.cif
_cod_data_source_block           07jo0039_0m
_cod_original_cell_volume        739.71(7)
_cod_database_code               4107660
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
C1 C 0.5651(3) 0.5848(3) 1.00059(17) 0.0189(5) Uani 1 1 d .
C2 C 0.6051(3) 0.4703(2) 0.9322(2) 0.0199(6) Uani 1 1 d .
H2 H 0.5364 0.3956 0.9536 0.024 Uiso 1 1 calc R
C3 C 0.7344(3) 0.4663(2) 0.84084(19) 0.0178(6) Uani 1 1 d .
C4 C 0.8246(3) 0.5878(2) 0.79678(16) 0.0166(5) Uani 1 1 d .
C5 C 1.0364(3) 0.6148(2) 0.86824(19) 0.0196(6) Uani 1 1 d .
H5A H 1.0228 0.6065 0.9594 0.024 Uiso 1 1 calc R
H5B H 1.1382 0.5519 0.8441 0.024 Uiso 1 1 calc R
C6 C 1.1159(3) 0.7451(2) 0.8406(2) 0.0229(6) Uani 1 1 d .
H6A H 1.1476 0.7495 0.7516 0.027 Uiso 1 1 calc R
H6B H 1.2459 0.7604 0.8929 0.027 Uiso 1 1 calc R
C7 C 0.9599(3) 0.8467(2) 0.8664(2) 0.0218(5) Uani 1 1 d .
H7A H 1.0139 0.929 0.8419 0.026 Uiso 1 1 calc R
H7B H 0.94 0.8492 0.9572 0.026 Uiso 1 1 calc R
C8 C 0.7532(4) 0.8219(2) 0.7933(2) 0.0190(6) Uani 1 1 d .
H8A H 0.6516 0.8855 0.8162 0.023 Uiso 1 1 calc R
H8B H 0.7702 0.8299 0.7025 0.023 Uiso 1 1 calc R
C9 C 0.6712(3) 0.6935(2) 0.81975(19) 0.0165(5) Uani 1 1 d .
H9 H 0.5402 0.6792 0.7663 0.02 Uiso 1 1 calc R
C10 C 0.8513(3) 0.5784(2) 0.65541(17) 0.0181(5) Uani 1 1 d .
C11 C 0.8008(4) 0.3454(2) 0.7854(2) 0.0265(6) Uani 1 1 d .
H11A H 0.7386 0.2755 0.8283 0.04 Uiso 1 1 calc R
H11B H 0.9519 0.3387 0.7957 0.04 Uiso 1 1 calc R
H11C H 0.7553 0.3432 0.696 0.04 Uiso 1 1 calc R
C12 C 0.6434(3) 0.5814(3) 0.45179(15) 0.0200(5) Uani 1 1 d .
C13 C 0.4111(3) 0.5893(3) 0.42598(18) 0.0239(5) Uani 1 1 d .
H13A H 0.3604 0.6665 0.4624 0.036 Uiso 1 1 calc R
H13B H 0.3462 0.5171 0.4636 0.036 Uiso 1 1 calc R
H13C H 0.3763 0.5894 0.3353 0.036 Uiso 1 1 calc R
C14 C 0.7255(4) 0.4594(2) 0.4038(2) 0.0282(6) Uani 1 1 d .
H14A H 0.6568 0.3893 0.4426 0.042 Uiso 1 1 calc R
H14B H 0.8749 0.4546 0.425 0.042 Uiso 1 1 calc R
H14C H 0.6978 0.4554 0.3125 0.042 Uiso 1 1 calc R
C15 C 0.7498(4) 0.6950(3) 0.4009(2) 0.0344(7) Uani 1 1 d .
H15A H 0.9 0.6862 0.4166 0.052 Uiso 1 1 calc R
H15B H 0.7038 0.7705 0.4427 0.052 Uiso 1 1 calc R
H15C H 0.7143 0.7018 0.3105 0.052 Uiso 1 1 calc R
O1 O 0.4905(2) 0.58759(18) 1.10132(12) 0.0278(4) Uani 1 1 d .
O2 O 0.6258(2) 0.69405(14) 0.95121(13) 0.0174(4) Uani 1 1 d .
O3 O 1.0144(2) 0.56427(17) 0.61087(12) 0.0286(4) Uani 1 1 d .
O4 O 0.66647(18) 0.58431(16) 0.59109(11) 0.0186(3) 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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 O2 118.2(2)
O1 C1 C2 124.3(2)
O2 C1 C2 117.48(16)
C3 C2 C1 122.6(2)
C3 C2 H2 118.7
C1 C2 H2 118.7
C2 C3 C11 122.1(2)
C2 C3 C4 118.6(2)
C11 C3 C4 119.21(18)
C3 C4 C9 108.19(15)
C3 C4 C10 108.91(19)
C9 C4 C10 109.09(17)
C3 C4 C5 110.78(17)
C9 C4 C5 110.17(19)
C10 C4 C5 109.67(15)
C6 C5 C4 112.03(17)
C6 C5 H5A 109.2
C4 C5 H5A 109.2
C6 C5 H5B 109.2
C4 C5 H5B 109.2
H5A C5 H5B 107.9
C5 C6 C7 112.26(17)
C5 C6 H6A 109.2
C7 C6 H6A 109.2
C5 C6 H6B 109.2
C7 C6 H6B 109.2
H6A C6 H6B 107.9
C6 C7 C8 110.72(18)
C6 C7 H7A 109.5
C8 C7 H7A 109.5
C6 C7 H7B 109.5
C8 C7 H7B 109.5
H7A C7 H7B 108.1
C9 C8 C7 111.78(19)
C9 C8 H8A 109.3
C7 C8 H8A 109.3
C9 C8 H8B 109.3
C7 C8 H8B 109.3
H8A C8 H8B 107.9
O2 C9 C8 106.07(17)
O2 C9 C4 109.68(16)
C8 C9 C4 113.52(18)
O2 C9 H9 109.2
C8 C9 H9 109.2
C4 C9 H9 109.2
O3 C10 O4 125.65(17)
O3 C10 C4 124.43(16)
O4 C10 C4 109.89(15)
C3 C11 H11A 109.5
C3 C11 H11B 109.5
H11A C11 H11B 109.5
C3 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
O4 C12 C14 110.31(18)
O4 C12 C13 101.87(13)
C14 C12 C13 110.9(2)
O4 C12 C15 109.16(19)
C14 C12 C15 112.81(17)
C13 C12 C15 111.2(2)
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C12 C14 H14A 109.5
C12 C14 H14B 109.5
H14A C14 H14B 109.5
C12 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C12 C15 H15A 109.5
C12 C15 H15B 109.5
H15A C15 H15B 109.5
C12 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C1 O2 C9 117.31(16)
C10 O4 C12 122.24(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.214(2)
C1 O2 1.353(3)
C1 C2 1.460(4)
C2 C3 1.335(3)
C2 H2 0.95
C3 C11 1.499(4)
C3 C4 1.515(4)
C4 C9 1.537(3)
C4 C10 1.538(3)
C4 C5 1.548(3)
C5 C6 1.522(3)
C5 H5A 0.99
C5 H5B 0.99
C6 C7 1.524(3)
C6 H6A 0.99
C6 H6B 0.99
C7 C8 1.523(3)
C7 H7A 0.99
C7 H7B 0.99
C8 C9 1.507(3)
C8 H8A 0.99
C8 H8B 0.99
C9 O2 1.458(3)
C9 H9 1
C10 O3 1.201(2)
C10 O4 1.338(2)
C11 H11A 0.98
C11 H11B 0.98
C11 H11C 0.98
C12 O4 1.487(2)
C12 C14 1.512(4)
C12 C13 1.513(3)
C12 C15 1.518(4)
C13 H13A 0.98
C13 H13B 0.98
C13 H13C 0.98
C14 H14A 0.98
C14 H14B 0.98
C14 H14C 0.98
C15 H15A 0.98
C15 H15B 0.98
C15 H15C 0.98
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 -161.7(2)
O2 C1 C2 C3 14.6(3)
C1 C2 C3 C11 169.96(19)
C1 C2 C3 C4 -6.9(3)
C2 C3 C4 C9 -27.7(3)
C11 C3 C4 C9 155.33(18)
C2 C3 C4 C10 -146.15(19)
C11 C3 C4 C10 36.9(2)
C2 C3 C4 C5 93.2(2)
C11 C3 C4 C5 -83.8(2)
C3 C4 C5 C6 -171.38(17)
C9 C4 C5 C6 -51.7(2)
C10 C4 C5 C6 68.4(2)
C4 C5 C6 C7 54.6(2)
C5 C6 C7 C8 -55.4(2)
C6 C7 C8 C9 54.9(2)
C7 C8 C9 O2 65.9(2)
C7 C8 C9 C4 -54.6(2)
C3 C4 C9 O2 55.1(2)
C10 C4 C9 O2 173.40(16)
C5 C4 C9 O2 -66.2(2)
C3 C4 C9 C8 173.50(17)
C10 C4 C9 C8 -68.2(2)
C5 C4 C9 C8 52.3(2)
C3 C4 C10 O3 -105.1(3)
C9 C4 C10 O3 137.0(2)
C5 C4 C10 O3 16.3(3)
C3 C4 C10 O4 72.9(2)
C9 C4 C10 O4 -45.0(3)
C5 C4 C10 O4 -165.7(2)
O1 C1 O2 C9 -166.67(16)
C2 C1 O2 C9 16.9(2)
C8 C9 O2 C1 -174.81(16)
C4 C9 O2 C1 -51.8(2)
O3 C10 O4 C12 -3.8(4)
C4 C10 O4 C12 178.2(2)
C14 C12 O4 C10 61.8(3)
C13 C12 O4 C10 179.6(2)
C15 C12 O4 C10 -62.7(3)
