#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/34/7103471.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_7103471
loop_
_publ_author_name
'Fabra, María J'
'Fraile, José M'
'Herrerías, Clara I'
'Lahoz, Fernando J'
'Mayoral, José A'
'Pérez, Ignacio'
_publ_section_title
;
 Surface-enhanced stereoselectivity in Mukaiyama aldol reactions
 catalyzed by clay-supported bis(oxazoline)-copper complexes.
;
_journal_issue                   42
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              5402
_journal_page_last               5404
_journal_paper_doi               10.1039/b809956a
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H12 O5'
_chemical_formula_sum            'C13 H12 O5'
_chemical_formula_weight         248.23
_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                 102.73(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.5836(15)
_cell_length_b                   5.7612(12)
_cell_length_c                   13.331(3)
_cell_measurement_reflns_used    4998
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.4687
_cell_measurement_theta_min      3.3908
_cell_volume                     568.1(2)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May 8 2007,13:10:02)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May 8 2007,13:10:02)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May 8 2007,13:10:02)
;
_computing_molecular_graphics    'XP program, SHELXTL v6.12, Bruker2000'
_computing_publication_material  'XCIF program, SHELXTLv6.12, BrukerAXS'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.2640
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Oxford diffraction Xcalibur Nova'
_diffrn_measurement_method       'ω rotations with narrow frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Nova micro-focus (Cu) X-ray source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0184
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5624
_diffrn_reflns_theta_full        72
_diffrn_reflns_theta_max         73.78
_diffrn_reflns_theta_min         3.40
_diffrn_standards_decay_%        'no decay'
_exptl_absorpt_coefficient_mu    0.949
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_correction_T_min  0.812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May 8 2007,13:10:02)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular block'
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.124
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.074
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2199
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0316
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0384P)²+0.2259P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0841
_reflns_number_gt                2088
_reflns_number_total             2199
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b809956a.txt
_cod_data_source_block           compound_11
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7103471
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9224(2) 0.3169(3) 0.71185(14) 0.0195(4) Uani 1 1 d . . .
C2 C 0.8490(2) 0.5160(3) 0.63675(14) 0.0199(4) Uani 1 1 d . . .
C3 C 0.9014(3) 0.5063(3) 0.53483(14) 0.0243(4) Uani 1 1 d . . .
C4 C 0.7543(3) 0.4944(4) 0.46060(15) 0.0289(4) Uani 1 1 d . . .
C5 C 0.5962(3) 0.4910(4) 0.50655(15) 0.0271(4) Uani 1 1 d . . .
C6 C 1.1302(2) 0.3302(4) 0.74532(13) 0.0205(4) Uani 1 1 d . . .
C7 C 1.3812(3) 0.5843(4) 0.77496(17) 0.0280(4) Uani 1 1 d . . .
C8 C 0.8503(2) 0.3403(3) 0.81035(14) 0.0203(4) Uani 1 1 d . . .
C9 C 0.8860(2) 0.5406(3) 0.87055(14) 0.0219(4) Uani 1 1 d . . .
C10 C 0.8294(2) 0.5578(4) 0.96249(15) 0.0254(4) Uani 1 1 d . . .
C11 C 0.7347(3) 0.3767(4) 0.99495(15) 0.0263(4) Uani 1 1 d . . .
C12 C 0.6960(3) 0.1803(4) 0.93428(16) 0.0270(4) Uani 1 1 d . . .
C13 C 0.7542(2) 0.1603(3) 0.84278(14) 0.0229(4) Uani 1 1 d . . .
O1 O 0.88505(18) 0.0996(2) 0.66426(10) 0.0224(3) Uani 1 1 d . . .
O2 O 0.43650(19) 0.4854(3) 0.46746(12) 0.0355(4) Uani 1 1 d . . .
O3 O 0.65417(16) 0.4947(2) 0.61037(9) 0.0229(3) Uani 1 1 d . . .
O4 O 1.22555(17) 0.1665(2) 0.77340(10) 0.0264(3) Uani 1 1 d . . .
O5 O 1.18713(16) 0.5487(2) 0.74095(10) 0.0241(3) Uani 1 1 d . . .
H9 H 0.955(3) 0.668(5) 0.8483(18) 0.031(6) Uiso 1 1 d . . .
H13 H 0.733(3) 0.019(4) 0.8010(17) 0.021(5) Uiso 1 1 d . . .
H12 H 0.633(3) 0.054(5) 0.9548(19) 0.034(6) Uiso 1 1 d . . .
H4 H 0.749(3) 0.489(5) 0.390(2) 0.041(7) Uiso 1 1 d . . .
H7A H 1.440(3) 0.503(5) 0.7252(19) 0.035(6) Uiso 1 1 d . . .
H10 H 0.859(3) 0.697(5) 1.0055(19) 0.033(6) Uiso 1 1 d . . .
H2 H 0.883(3) 0.668(4) 0.6686(15) 0.014(5) Uiso 1 1 d . . .
H7B H 1.424(3) 0.520(5) 0.8443(19) 0.029(6) Uiso 1 1 d . . .
H11 H 0.697(3) 0.392(4) 1.0627(18) 0.023(5) Uiso 1 1 d . . .
H3 H 1.026(3) 0.514(5) 0.5284(17) 0.028(6) Uiso 1 1 d . . .
H7C H 1.395(3) 0.759(5) 0.7749(18) 0.031(6) Uiso 1 1 d . . .
H1 H 0.775(4) 0.091(5) 0.633(2) 0.048(8) Uiso 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 0.0181 0.0091 '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 0.0492 0.0322 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C8 112.96(15) . . ?
O1 C1 C6 105.44(15) . . ?
C8 C1 C6 106.39(14) . . ?
O1 C1 C2 111.20(14) . . ?
C8 C1 C2 110.14(14) . . ?
C6 C1 C2 110.50(15) . . ?
O3 C2 C3 103.71(14) . . ?
O3 C2 C1 107.32(14) . . ?
C3 C2 C1 115.52(16) . . ?
O3 C2 H2 109.9(12) . . ?
C3 C2 H2 109.1(12) . . ?
C1 C2 H2 111.0(12) . . ?
C4 C3 C2 109.43(17) . . ?
C4 C3 H3 128.1(13) . . ?
C2 C3 H3 122.5(13) . . ?
C3 C4 C5 108.80(18) . . ?
C3 C4 H4 127.0(16) . . ?
C5 C4 H4 124.2(16) . . ?
O2 C5 O3 120.6(2) . . ?
O2 C5 C4 131.01(19) . . ?
O3 C5 C4 108.43(16) . . ?
O4 C6 O5 125.24(16) . . ?
O4 C6 C1 124.05(18) . . ?
O5 C6 C1 110.69(15) . . ?
O5 C7 H7A 107.3(14) . . ?
O5 C7 H7B 110.0(14) . . ?
H7A C7 H7B 110(2) . . ?
O5 C7 H7C 103.6(14) . . ?
H7A C7 H7C 114(2) . . ?
H7B C7 H7C 111(2) . . ?
C13 C8 C9 119.05(18) . . ?
C13 C8 C1 120.72(17) . . ?
C9 C8 C1 120.19(17) . . ?
C10 C9 C8 120.49(18) . . ?
C10 C9 H9 120.1(15) . . ?
C8 C9 H9 119.4(14) . . ?
C11 C10 C9 120.21(19) . . ?
C11 C10 H10 119.8(15) . . ?
C9 C10 H10 120.0(15) . . ?
C12 C11 C10 119.3(2) . . ?
C12 C11 H11 122.0(14) . . ?
C10 C11 H11 118.7(14) . . ?
C11 C12 C13 120.8(2) . . ?
C11 C12 H12 121.1(15) . . ?
C13 C12 H12 118.0(16) . . ?
C8 C13 C12 120.07(18) . . ?
C8 C13 H13 118.3(13) . . ?
C12 C13 H13 121.6(13) . . ?
C1 O1 H1 111(2) . . ?
C5 O3 C2 109.45(14) . . ?
C6 O5 C7 115.68(15) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.404(2) . ?
C1 C8 1.535(3) . ?
C1 C6 1.542(2) . ?
C1 C2 1.543(3) . ?
C2 O3 1.447(2) . ?
C2 C3 1.498(3) . ?
C2 H2 0.98(2) . ?
C3 C4 1.320(3) . ?
C3 H3 0.97(2) . ?
C4 C5 1.462(3) . ?
C4 H4 0.94(3) . ?
C5 O2 1.209(2) . ?
C5 O3 1.357(2) . ?
C6 O4 1.197(2) . ?
C6 O5 1.336(2) . ?
C7 O5 1.456(2) . ?
C7 H7A 1.00(3) . ?
C7 H7B 0.98(2) . ?
C7 H7C 1.01(3) . ?
C8 C13 1.390(3) . ?
C8 C9 1.397(3) . ?
C9 C10 1.389(3) . ?
C9 H9 0.98(3) . ?
C10 C11 1.388(3) . ?
C10 H10 0.98(3) . ?
C11 C12 1.384(3) . ?
C11 H11 1.01(2) . ?
C12 C13 1.390(3) . ?
C12 H12 0.94(3) . ?
C13 H13 0.98(2) . ?
O1 H1 0.85(3) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 O3 64.26(18) . . . . ?
C8 C1 C2 O3 -61.74(18) . . . . ?
C6 C1 C2 O3 -178.99(14) . . . . ?
O1 C1 C2 C3 -50.8(2) . . . . ?
C8 C1 C2 C3 -176.83(15) . . . . ?
C6 C1 C2 C3 65.9(2) . . . . ?
O3 C2 C3 C4 3.1(2) . . . . ?
C1 C2 C3 C4 120.26(18) . . . . ?
C2 C3 C4 C5 -1.0(2) . . . . ?
C3 C4 C5 O2 178.5(2) . . . . ?
C3 C4 C5 O3 -1.7(2) . . . . ?
O1 C1 C6 O4 -33.9(2) . . . . ?
C8 C1 C6 O4 86.2(2) . . . . ?
C2 C1 C6 O4 -154.21(17) . . . . ?
O1 C1 C6 O5 147.60(15) . . . . ?
C8 C1 C6 O5 -92.20(17) . . . . ?
C2 C1 C6 O5 27.3(2) . . . . ?
O1 C1 C8 C13 -1.9(2) . . . . ?
C6 C1 C8 C13 -117.08(18) . . . . ?
C2 C1 C8 C13 123.14(18) . . . . ?
O1 C1 C8 C9 175.97(15) . . . . ?
C6 C1 C8 C9 60.8(2) . . . . ?
C2 C1 C8 C9 -59.0(2) . . . . ?
C13 C8 C9 C10 1.3(2) . . . . ?
C1 C8 C9 C10 -176.59(16) . . . . ?
C8 C9 C10 C11 -0.8(3) . . . . ?
C9 C10 C11 C12 -0.6(3) . . . . ?
C10 C11 C12 C13 1.5(3) . . . . ?
C9 C8 C13 C12 -0.4(3) . . . . ?
C1 C8 C13 C12 177.42(16) . . . . ?
C11 C12 C13 C8 -0.9(3) . . . . ?
O2 C5 O3 C2 -176.39(18) . . . . ?
C4 C5 O3 C2 3.7(2) . . . . ?
C3 C2 O3 C5 -4.15(19) . . . . ?
C1 C2 O3 C5 -126.87(16) . . . . ?
O4 C6 O5 C7 -0.9(3) . . . . ?
C1 C6 O5 C7 177.57(15) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653070
