#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/33/1513394.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_1513394
loop_
_publ_author_name
'Alcoberro, Sandra'
'Gómez-Palomino, Alejandro'
'Solà, Ricard'
'Romea, Pedro'
'Urpí, Fèlix'
'Font-Bardia, Mercè'
_publ_section_title
;
 Stereoselective titanium-mediated aldol reactions of a chiral
 lactate-derived ethyl ketone with ketones.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              584
_journal_page_last               587
_journal_paper_doi               10.1021/ol403461b
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C8 H12 O4'
_chemical_formula_sum            'C8 H12 O4'
_chemical_formula_weight         172.18
_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                 104.486(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.4523(8)
_cell_length_b                   5.5812(5)
_cell_length_c                   10.7250(10)
_cell_measurement_reflns_used    1341
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.93
_cell_measurement_theta_min      3.01
_cell_volume                     431.90(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP (Brueggermann and Smith, 1990)'
_computing_publication_material  'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'high brilliance Incoatec Microfocus Source '
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0793
_diffrn_reflns_av_sigmaI/netI    0.0949
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5433
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.82
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             184
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         1976
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0982
_refine_ls_R_factor_gt           0.0542
_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)+(0.0513P)²+0.0241P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1284
_reflns_number_gt                1364
_reflns_number_total             1976
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol403461b_si_002.cif
_cod_data_source_block           mo_o31rb48_0m
_cod_original_sg_symbol_H-M      P21
_cod_database_code               1513394
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 0.4139(3) 0.2394(3) 0.68939(16) 0.0260(5) Uani 1 1 d .
O2 O 0.2499(3) -0.0344(3) 0.87860(18) 0.0278(5) Uani 1 1 d .
H3 H 0.323(5) -0.037(6) 0.956(3) 0.042 Uiso 1 1 d .
O3 O 0.5222(3) 0.4123(3) 0.87546(17) 0.0331(5) Uani 1 1 d .
O4 O -0.0090(3) -0.0917(4) 0.57944(18) 0.0411(6) Uani 1 1 d .
C1 C 0.3877(5) -0.1716(5) 0.6174(3) 0.0368(8) Uani 1 1 d .
H8 H 0.5040 -0.1527 0.5914 0.055 Uiso 1 1 calc R
H9 H 0.3078 -0.2863 0.5599 0.055 Uiso 1 1 calc R
H1 H 0.4144 -0.2311 0.7061 0.055 Uiso 1 1 calc R
C2 C 0.2905(4) 0.0677(5) 0.6092(2) 0.0256(6) Uani 1 1 d .
H10 H 0.2714 0.1241 0.5184 0.031 Uiso 1 1 calc R
C3 C 0.3987(4) 0.2954(4) 0.8080(2) 0.0242(7) Uani 1 1 d .
C4 C 0.2268(4) 0.2153(5) 0.8489(2) 0.0238(6) Uani 1 1 d .
C5 C 0.2035(4) 0.3604(5) 0.9622(3) 0.0322(7) Uani 1 1 d .
H11 H 0.0977 0.2989 0.9914 0.048 Uiso 1 1 calc R
H12 H 0.1815 0.5285 0.9366 0.048 Uiso 1 1 calc R
H2 H 0.3162 0.3481 1.0325 0.048 Uiso 1 1 calc R
C6 C 0.1025(4) 0.0544(5) 0.6349(2) 0.0281(7) Uani 1 1 d .
C7 C 0.0619(4) 0.2318(5) 0.7293(2) 0.0285(7) Uani 1 1 d .
H7 H 0.0637 0.3953 0.6916 0.034 Uiso 1 1 calc R
C8 C -0.1237(5) 0.1964(8) 0.7553(3) 0.0478(10) Uani 1 1 d .
H6 H -0.2194 0.1994 0.6738 0.072 Uiso 1 1 calc R
H5 H -0.1472 0.3251 0.8113 0.072 Uiso 1 1 calc R
H4 H -0.1267 0.0415 0.7977 0.072 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0301(11) 0.0231(9) 0.0223(9) -0.0029(8) 0.0017(8) -0.0050(9)
O2 0.0349(12) 0.0190(9) 0.0247(10) 0.0026(8) -0.0017(9) -0.0025(9)
O3 0.0348(12) 0.0283(11) 0.0291(10) 0.0003(9) -0.0051(9) -0.0080(10)
O4 0.0439(14) 0.0407(12) 0.0320(11) -0.0066(10) -0.0028(10) -0.0157(12)
C1 0.050(2) 0.0252(15) 0.0301(16) -0.0012(12) 0.0001(14) 0.0081(15)
C2 0.0324(17) 0.0210(12) 0.0188(14) -0.0015(11) -0.0022(12) -0.0030(13)
C3 0.0236(16) 0.0174(12) 0.0253(14) 0.0040(11) -0.0055(12) 0.0032(12)
C4 0.0266(16) 0.0195(12) 0.0218(13) -0.0031(11) -0.0008(11) -0.0006(13)
C5 0.0368(18) 0.0259(15) 0.0325(17) -0.0028(12) 0.0061(13) -0.0003(14)
C6 0.0319(17) 0.0255(14) 0.0196(14) 0.0035(12) -0.0072(12) -0.0037(14)
C7 0.0203(16) 0.0330(15) 0.0284(14) 0.0011(14) -0.0012(12) 0.0031(14)
C8 0.033(2) 0.074(3) 0.0357(17) 0.0027(18) 0.0061(14) -0.0025(19)
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
C3 O1 C2 121.6(2)
C4 O2 H3 104(2)
C2 C1 H8 109.5
C2 C1 H9 109.5
H8 C1 H9 109.5
C2 C1 H1 109.5
H8 C1 H1 109.5
H9 C1 H1 109.5
O1 C2 C6 114.0(2)
O1 C2 C1 109.0(2)
C6 C2 C1 113.8(3)
O1 C2 H10 106.5
C6 C2 H10 106.5
C1 C2 H10 106.5
O3 C3 O1 117.4(3)
O3 C3 C4 123.7(3)
O1 C3 C4 118.8(2)
O2 C4 C5 112.1(2)
O2 C4 C3 106.7(2)
C5 C4 C3 110.5(2)
O2 C4 C7 105.7(2)
C5 C4 C7 114.3(2)
C3 C4 C7 107.2(2)
C4 C5 H11 109.5
C4 C5 H12 109.5
H11 C5 H12 109.5
C4 C5 H2 109.5
H11 C5 H2 109.5
H12 C5 H2 109.5
O4 C6 C2 120.2(3)
O4 C6 C7 123.2(3)
C2 C6 C7 116.6(2)
C8 C7 C6 113.1(3)
C8 C7 C4 114.9(2)
C6 C7 C4 105.6(2)
C8 C7 H7 107.6
C6 C7 H7 107.6
C4 C7 H7 107.6
C7 C8 H6 109.5
C7 C8 H5 109.5
H6 C8 H5 109.5
C7 C8 H4 109.5
H6 C8 H4 109.5
H5 C8 H4 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.342(3)
O1 C2 1.452(3)
O2 C4 1.430(3)
O2 H3 0.87(3)
O3 C3 1.210(3)
O4 C6 1.209(3)
C1 C2 1.512(4)
C1 H8 0.9800
C1 H9 0.9800
C1 H1 0.9800
C2 C6 1.496(4)
C2 H10 1.0000
C3 C4 1.522(4)
C4 C5 1.506(4)
C4 C7 1.541(3)
C5 H11 0.9800
C5 H12 0.9800
C5 H2 0.9800
C6 C7 1.500(4)
C7 C8 1.491(4)
C7 H7 1.0000
C8 H6 0.9800
C8 H5 0.9800
C8 H4 0.9800
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
C3 O1 C2 C6 28.8(3)
C3 O1 C2 C1 -99.5(3)
C2 O1 C3 O3 169.5(2)
C2 O1 C3 C4 -12.1(3)
O3 C3 C4 O2 -104.7(3)
O1 C3 C4 O2 77.0(3)
O3 C3 C4 C5 17.4(4)
O1 C3 C4 C5 -160.9(2)
O3 C3 C4 C7 142.5(3)
O1 C3 C4 C7 -35.8(3)
O1 C2 C6 O4 -175.8(2)
C1 C2 C6 O4 -49.9(3)
O1 C2 C6 C7 5.2(3)
C1 C2 C6 C7 131.1(3)
O4 C6 C7 C8 4.5(4)
C2 C6 C7 C8 -176.5(2)
O4 C6 C7 C4 131.0(3)
C2 C6 C7 C4 -50.0(3)
O2 C4 C7 C8 75.5(3)
C5 C4 C7 C8 -48.2(4)
C3 C4 C7 C8 -171.0(3)
O2 C4 C7 C6 -49.8(3)
C5 C4 C7 C6 -173.5(2)
C3 C4 C7 C6 63.7(3)
