#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:58:49 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178831 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/85/4108556.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_4108556
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 unk
_chemical_formula_sum            'C12 H19 N O7'
_chemical_formula_weight         289.28
_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                   8.9755(4)
_cell_length_b                   10.0418(4)
_cell_length_c                   15.1088(7)
_cell_measurement_reflns_used    9157
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      35.04
_cell_measurement_theta_min      2.43
_cell_volume                     1361.76(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0163
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            41571
_diffrn_reflns_theta_full        33.14
_diffrn_reflns_theta_max         33.14
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.9733
_exptl_absorpt_correction_T_min  0.9170
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Sheldrick, 1997'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_description       irregular
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.76
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2931
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0292
_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)+(0.0492P)²+0.1423P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0766
_refine_ls_wR_factor_ref         0.0791
_reflns_number_gt                2727
_reflns_number_total             2931
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja805680z_si_002.cif
_cod_data_source_block           rovis33_0m
_cod_database_code               4108556
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
C1 C 0.92153(15) 0.94594(12) 0.19235(9) 0.0224(2) Uani 1 1 d .
H1A H 1.0009 0.9756 0.2312 0.027 Uiso 1 1 calc R
H1B H 0.9355 0.9880 0.1351 0.027 Uiso 1 1 calc R
C2 C 0.92931(13) 0.79543(11) 0.18190(7) 0.0174(2) Uani 1 1 d .
H2A H 1.0236 0.7706 0.1552 0.021 Uiso 1 1 calc R
H2B H 0.9228 0.7532 0.2395 0.021 Uiso 1 1 calc R
C3 C 0.66224(14) 0.94420(12) 0.17129(8) 0.0187(2) Uani 1 1 d .
H3A H 0.6739 0.9867 0.1140 0.022 Uiso 1 1 calc R
H3B H 0.5679 0.9729 0.1961 0.022 Uiso 1 1 calc R
C4 C 0.66027(12) 0.79415(11) 0.15929(7) 0.01609(19) Uani 1 1 d .
H4A H 0.6395 0.7512 0.2154 0.019 Uiso 1 1 calc R
H4B H 0.5826 0.7694 0.1178 0.019 Uiso 1 1 calc R
C5 C 0.83196(12) 0.66884(10) 0.05683(6) 0.01363(18) Uani 1 1 d .
C6 C 0.69979(12) 0.60657(10) 0.00798(6) 0.01400(18) Uani 1 1 d .
H6A H 0.6111 0.6629 0.0134 0.017 Uiso 1 1 calc R
C7 C 0.66674(12) 0.46336(10) 0.04080(7) 0.01331(17) Uani 1 1 d .
H7 H 0.5640 0.4411 0.0246 0.016 Uiso 1 1 calc R
C8 C 0.77195(12) 0.38031(10) -0.01724(6) 0.01285(17) Uani 1 1 d .
H8 H 0.8688 0.3701 0.0119 0.015 Uiso 1 1 calc R
C9 C 0.78767(13) 0.46530(11) -0.09937(7) 0.01523(18) Uani 1 1 d .
C10 C 0.68422(15) 0.44318(11) 0.14011(7) 0.0195(2) Uani 1 1 d .
H10A H 0.6138 0.5002 0.1708 0.023 Uiso 1 1 calc R
H10B H 0.7837 0.4703 0.1575 0.023 Uiso 1 1 calc R
C11 C 0.65896(17) 0.29945(12) 0.16906(8) 0.0251(3) Uani 1 1 d .
H11A H 0.7335 0.2434 0.1428 0.038 Uiso 1 1 calc R
H11B H 0.5620 0.2708 0.1502 0.038 Uiso 1 1 calc R
H11C H 0.6655 0.2937 0.2324 0.038 Uiso 1 1 calc R
C12 C 0.71201(12) 0.24523(10) -0.04520(6) 0.01441(18) Uani 1 1 d .
H1 H 0.646(3) -0.101(2) -0.0793(14) 0.048(6) Uiso 1 1 d .
H2 H 0.730(2) -0.056(2) -0.1549(14) 0.037(5) Uiso 1 1 d .
N1 N 0.80604(10) 0.75020(9) 0.12571(6) 0.01421(16) Uani 1 1 d .
O1 O 0.78086(10) 0.98502(9) 0.22839(6) 0.02214(18) Uani 1 1 d .
O2 O 0.95906(9) 0.63618(8) 0.03287(5) 0.01700(16) Uani 1 1 d .
O3 O 0.74144(10) 0.59121(8) -0.08362(5) 0.01697(16) Uani 1 1 d .
O4 O 0.82967(12) 0.43138(9) -0.17136(5) 0.02291(18) Uani 1 1 d .
O5 O 0.59033(10) 0.23171(9) -0.07874(6) 0.02119(17) Uani 1 1 d .
O6 O 0.80747(10) 0.14814(8) -0.03088(6) 0.02251(18) Uani 1 1 d .
H6 H 0.7763 0.0794 -0.0535 0.034 Uiso 1 1 calc R
O7 O 0.73741(11) -0.07885(8) -0.09853(6) 0.02008(17) 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 0.0000 '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'
N N 0.0061 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 110.66(10)
N1 C2 C1 109.46(10)
O1 C3 C4 111.42(10)
N1 C4 C3 109.19(10)
O2 C5 N1 123.09(10)
O2 C5 C6 117.64(9)
N1 C5 C6 119.19(9)
O3 C6 C5 107.79(9)
O3 C6 C7 104.92(8)
C5 C6 C7 111.90(8)
C10 C7 C8 115.30(9)
C10 C7 C6 114.78(8)
C8 C7 C6 101.75(8)
C9 C8 C12 107.99(8)
C9 C8 C7 102.68(8)
C12 C8 C7 115.22(8)
O4 C9 O3 121.42(10)
O4 C9 C8 127.77(10)
O3 C9 C8 110.77(8)
C7 C10 C11 113.16(9)
O5 C12 O6 124.94(10)
O5 C12 C8 122.38(10)
O6 C12 C8 112.66(9)
C5 N1 C2 120.40(9)
C5 N1 C4 127.14(9)
C2 N1 C4 112.23(8)
C1 O1 C3 110.42(9)
C9 O3 C6 110.40(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.4299(16)
C1 C2 1.5212(17)
C2 N1 1.4667(14)
C3 O1 1.4304(15)
C3 C4 1.5178(16)
C4 N1 1.4710(14)
C5 O2 1.2409(13)
C5 N1 1.3434(13)
C5 C6 1.5308(15)
C6 O3 1.4418(12)
C6 C7 1.5499(14)
C7 C10 1.5223(15)
C7 C8 1.5351(14)
C8 C9 1.5126(14)
C8 C12 1.5191(14)
C9 O4 1.2005(13)
C9 O3 1.3518(13)
C10 C11 1.5251(16)
C12 O5 1.2116(14)
C12 O6 1.3158(14)
