#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/85/4108557.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_4108557
loop_
_publ_author_name
'Qin Liu'
'Stéphane Perreault'
'Tomislav Rovis'
_publ_section_title
;
 Catalytic Asymmetric Intermolecular Stetter Reaction of Glyoxamides with
 Alkylidenemalonates
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14066
_journal_page_last               14067
_journal_paper_doi               10.1021/ja805680z
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration ab
_chemical_formula_sum            'C13 H19 O7'
_chemical_formula_weight         287.28
_chemical_name_systematic
;                                                                              
 ?                                                                             
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9730(14)
_cell_length_b                   10.0535(15)
_cell_length_c                   15.128(2)
_cell_measurement_reflns_used    1024
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      60.42
_cell_measurement_theta_min      5.28
_cell_volume                     1364.7(3)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_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    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.931
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_device_type  'MWPC area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19862
_diffrn_reflns_theta_full        60.02
_diffrn_reflns_theta_max         60.02
_diffrn_reflns_theta_min         7.23
_exptl_absorpt_coefficient_mu    0.970
_exptl_absorpt_correction_T_max  0.8525
_exptl_absorpt_correction_T_min  0.8149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       'plate     '
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         1905
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0307
_refine_ls_shift/su_max          0.065
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0600P)²+0.1951P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0796
_reflns_number_gt                1848
_reflns_number_total             1905
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja805680z_si_003.cif
_cod_data_source_block           csu
_cod_original_cell_volume        1364.7(4)
_cod_database_code               4108557
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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
O1WA O 0.73703(15) -0.07816(12) 0.40092(9) 0.0269(3) Uani 1 1 d .
H1WA H 0.7263 -0.0510 0.3483 0.032 Uiso 1 1 d R
H2WA H 0.7911 -0.1459 0.3915 0.032 Uiso 1 1 d R
O1 O 0.74207(15) 0.59127(12) 0.41686(8) 0.0239(3) Uani 1 1 d .
C1 C 0.7872(2) 0.46599(18) 0.40106(11) 0.0212(4) Uani 1 1 d .
O2 O 0.82966(17) 0.43215(14) 0.32881(9) 0.0312(4) Uani 1 1 d .
C2 C 0.7723(2) 0.38044(18) 0.48238(11) 0.0194(4) Uani 1 1 d .
H2A H 0.8714 0.3698 0.5118 0.023 Uiso 1 1 calc R
O3 O 0.59084(14) 0.23198(13) 0.42125(9) 0.0291(3) Uani 1 1 d .
C3 C 0.6675(2) 0.46318(18) 0.54109(12) 0.0200(4) Uani 1 1 d .
H3A H 0.5625 0.4404 0.5249 0.024 Uiso 1 1 calc R
O4 O 0.80744(15) 0.14905(12) 0.46852(9) 0.0299(3) Uani 1 1 d .
H4 H 0.7752 0.0742 0.4512 0.036 Uiso 1 1 d R
C4 C 0.6999(2) 0.60609(18) 0.50829(11) 0.0209(4) Uani 1 1 d .
H4A H 0.6092 0.6634 0.5139 0.025 Uiso 1 1 calc R
O5 O 0.95889(14) 0.63627(12) 0.53305(8) 0.0244(3) Uani 1 1 d .
C5 C 0.71201(19) 0.24567(18) 0.45454(11) 0.0204(4) Uani 1 1 d .
O6 O 0.78065(16) 0.98425(13) 0.72820(8) 0.0303(4) Uani 1 1 d .
C6 C 0.6859(3) 0.44173(18) 0.64018(13) 0.0280(4) Uani 1 1 d .
H6A H 0.7880 0.4683 0.6575 0.034 Uiso 1 1 calc R
H6B H 0.6152 0.5003 0.6719 0.034 Uiso 1 1 calc R
C7 C 0.6598(3) 0.3002(2) 0.66882(13) 0.0347(5) Uani 1 1 d .
H7A H 0.6763 0.2927 0.7327 0.052 Uiso 1 1 calc R
H7B H 0.7290 0.2413 0.6375 0.052 Uiso 1 1 calc R
H7C H 0.5571 0.2746 0.6549 0.052 Uiso 1 1 calc R
C8 C 0.8323(2) 0.66840(17) 0.55675(11) 0.0201(4) Uani 1 1 d .
C9 C 0.80643(16) 0.74958(14) 0.62579(10) 0.0104(3) Uani 1 1 d .
C10 C 0.9301(2) 0.79603(19) 0.68199(12) 0.0254(4) Uani 1 1 d .
H10A H 1.0265 0.7712 0.6548 0.030 Uiso 1 1 calc R
H10B H 0.9239 0.7531 0.7408 0.030 Uiso 1 1 calc R
C11 C 0.9214(2) 0.9454(2) 0.69220(14) 0.0300(5) Uani 1 1 d .
H11A H 1.0024 0.9761 0.7317 0.036 Uiso 1 1 calc R
H11B H 0.9354 0.9881 0.6338 0.036 Uiso 1 1 calc R
C12 C 0.6620(2) 0.94326(19) 0.67147(13) 0.0252(4) Uani 1 1 d .
H12A H 0.6734 0.9867 0.6131 0.030 Uiso 1 1 calc R
H12B H 0.5657 0.9722 0.6970 0.030 Uiso 1 1 calc R
C13 C 0.6606(2) 0.79433(18) 0.65946(12) 0.0227(4) Uani 1 1 d .
H13A H 0.6394 0.7505 0.7167 0.027 Uiso 1 1 calc R
H13B H 0.5812 0.7691 0.6172 0.027 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 0.0181 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
C1 O1 C4 110.28(13)
O2 C1 O1 121.36(16)
O2 C1 C2 127.35(17)
O1 C1 C2 111.27(15)
C1 C2 C5 108.33(14)
C1 C2 C3 102.54(14)
C5 C2 C3 115.14(14)
C6 C3 C2 115.17(16)
C6 C3 C4 115.25(15)
C2 C3 C4 101.66(14)
O1 C4 C8 107.33(14)
O1 C4 C3 105.13(13)
C8 C4 C3 111.86(15)
O3 C5 O4 124.83(17)
O3 C5 C2 122.59(16)
O4 C5 C2 112.55(15)
C12 O6 C11 110.54(14)
C7 C6 C3 113.58(16)
O5 C8 C9 122.87(16)
O5 C8 C4 117.93(16)
C9 C8 C4 119.10(15)
C8 C9 C13 127.31(14)
C8 C9 C10 120.67(15)
C13 C9 C10 111.86(14)
C9 C10 C11 109.56(16)
O6 C11 C10 110.85(16)
O6 C12 C13 111.39(16)
C9 C13 C12 109.72(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.344(2)
O1 C4 1.442(2)
C1 O2 1.206(2)
C1 C2 1.507(2)
C2 C5 1.519(2)
C2 C3 1.538(3)
O3 C5 1.206(2)
C3 C6 1.523(3)
C3 C4 1.548(3)
O4 C5 1.312(2)
C4 C8 1.530(3)
O5 C8 1.234(2)
O6 C12 1.428(3)
O6 C11 1.430(3)
C6 C7 1.506(3)
C8 C9 1.346(2)
C9 C13 1.474(2)
C9 C10 1.474(2)
C10 C11 1.512(3)
C12 C13 1.508(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
C4 O1 C1 O2 -178.94(16)
C4 O1 C1 C2 2.7(2)
O2 C1 C2 C5 -39.6(2)
O1 C1 C2 C5 138.63(15)
O2 C1 C2 C3 -161.78(18)
O1 C1 C2 C3 16.47(19)
C1 C2 C3 C6 -152.28(15)
C5 C2 C3 C6 90.31(19)
C1 C2 C3 C4 -26.95(17)
C5 C2 C3 C4 -144.36(15)
C1 O1 C4 C8 98.45(16)
C1 O1 C4 C3 -20.78(19)
C6 C3 C4 O1 154.71(16)
C2 C3 C4 O1 29.44(17)
C6 C3 C4 C8 38.6(2)
C2 C3 C4 C8 -86.72(16)
C1 C2 C5 O3 -62.8(2)
C3 C2 C5 O3 51.3(2)
C1 C2 C5 O4 115.36(17)
C3 C2 C5 O4 -130.55(16)
C2 C3 C6 C7 -59.6(2)
C4 C3 C6 C7 -177.53(17)
O1 C4 C8 O5 -35.5(2)
C3 C4 C8 O5 79.36(19)
O1 C4 C8 C9 148.05(14)
C3 C4 C8 C9 -97.14(18)
O5 C8 C9 C13 179.87(16)
C4 C8 C9 C13 -3.8(2)
O5 C8 C9 C10 -5.2(2)
C4 C8 C9 C10 171.14(15)
C8 C9 C10 C11 129.91(17)
C13 C9 C10 C11 -54.4(2)
C12 O6 C11 C10 -60.2(2)
C9 C10 C11 O6 57.1(2)
C11 O6 C12 C13 59.9(2)
C8 C9 C13 C12 -130.85(18)
C10 C9 C13 C12 53.83(19)
O6 C12 C13 C9 -56.1(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660340
