#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:43:19 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178440 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/61/4026153.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_4026153
loop_
_publ_author_name
'Claudio Curti'
'Lucia Battistini'
'Beatrice Ranieri'
'Giorgio Pelosi'
'Gloria Rassu'
'Giovanni Casiraghi'
'Franca Zanardi'
_publ_section_title
;
 anti-Selective, Catalytic Asymmetric Vinylogous Mukaiyama Mannich
 Reactions of Pyrrole-Based Silyl Dienolates with N-Aryl Aldimines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2248
_journal_page_last               2252
_journal_paper_doi               10.1021/jo1021234
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C23 H26 N2 O4'
_chemical_formula_weight         394.46
_chemical_name_systematic
;
(R)-5-(N-tert-Butoxycarbonyl)-[(S)-(2-methoxyphenylamino)-
(phenyl)methyl]-1H-pirrol-2(5H)one
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   12.7109(7)
_cell_length_b                   17.8216(10)
_cell_length_c                   19.5965(11)
_cell_measurement_temperature    293(2)
_cell_volume                     4439.2(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0485
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            37759
_diffrn_reflns_theta_full        27.58
_diffrn_reflns_theta_max         27.58
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS (1999)'
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.822
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         5126
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.822
_refine_ls_R_factor_all          0.1137
_refine_ls_R_factor_gt           0.0510
_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)+(0.1226P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1518
_refine_ls_wR_factor_ref         0.1872
_reflns_number_gt                2232
_reflns_number_total             5126
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1021234_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               4026153
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
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 0.40884(15) -0.04831(13) 0.22156(10) 0.0663(5) Uani 1 1 d .
C2 C 0.31520(16) -0.00695(14) 0.23990(12) 0.0802(7) Uani 1 1 d .
H5 H 0.3151 0.0401 0.2605 0.096 Uiso 1 1 calc R
C3 C 0.23069(15) -0.04472(14) 0.22360(10) 0.0730(6) Uani 1 1 d .
H6 H 0.1624 -0.0284 0.2320 0.088 Uiso 1 1 calc R
C4 C 0.25723(14) -0.11652(12) 0.19012(10) 0.0573(5) Uani 1 1 d .
C5 C 0.21494(15) -0.12223(12) 0.11665(10) 0.0580(5) Uani 1 1 d .
C6 C 0.09551(15) -0.12639(11) 0.11594(10) 0.0616(5) Uani 1 1 d .
C7 C 0.04566(19) -0.18931(15) 0.13994(13) 0.0890(7) Uani 1 1 d .
H001 H 0.0854 -0.2295 0.1558 0.107 Uiso 1 1 calc R
C8 C -0.0642(3) -0.1938(2) 0.14094(16) 0.1193(11) Uani 1 1 d .
H017 H -0.0970 -0.2367 0.1576 0.143 Uiso 1 1 calc R
C9 C -0.1230(2) -0.1354(3) 0.11761(18) 0.1222(12) Uani 1 1 d .
H020 H -0.1960 -0.1384 0.1182 0.147 Uiso 1 1 calc R
C10 C -0.0753(2) -0.0732(2) 0.09356(15) 0.1060(9) Uani 1 1 d .
H021 H -0.1156 -0.0334 0.0776 0.127 Uiso 1 1 calc R
C11 C 0.03343(18) -0.06827(14) 0.09252(12) 0.0799(6) Uani 1 1 d .
H008 H 0.0652 -0.0250 0.0757 0.096 Uiso 1 1 calc R
C12 C 0.28082(15) -0.06583(13) 0.00919(11) 0.0696(6) Uani 1 1 d .
C13 C 0.25129(18) -0.12573(16) -0.03073(12) 0.0861(7) Uani 1 1 d .
H015 H 0.2114 -0.1646 -0.0124 0.103 Uiso 1 1 calc R
C14 C 0.2827(3) -0.1273(2) -0.10060(15) 0.1114(10) Uani 1 1 d .
H016 H 0.2639 -0.1674 -0.1285 0.134 Uiso 1 1 calc R
C15 C 0.3408(3) -0.0695(2) -0.12594(15) 0.1102(10) Uani 1 1 d .
H018 H 0.3629 -0.0715 -0.1711 0.132 Uiso 1 1 calc R
C16 C 0.3675(2) -0.0090(2) -0.08775(16) 0.1058(10) Uani 1 1 d .
H019 H 0.4048 0.0303 -0.1075 0.127 Uiso 1 1 calc R
C17 C 0.33960(16) -0.00549(15) -0.01965(12) 0.0784(7) Uani 1 1 d .
C18 C 0.4187(3) 0.11353(18) -0.0012(2) 0.1309(12) Uani 1 1 d .
H20A H 0.4287 0.1492 0.0349 0.196 Uiso 1 1 calc R
H20B H 0.3799 0.1365 -0.0377 0.196 Uiso 1 1 calc R
H20C H 0.4860 0.0973 -0.0179 0.196 Uiso 1 1 calc R
C19 C 0.43679(18) -0.17589(12) 0.17605(10) 0.0685(6) Uani 1 1 d .
C20 C 0.4213(2) -0.30639(14) 0.13582(18) 0.1073(9) Uani 1 1 d .
C21 C 0.4765(3) -0.29009(19) 0.06972(18) 0.1368(12) Uani 1 1 d .
H13A H 0.4280 -0.2674 0.0384 0.205 Uiso 1 1 calc R
H13B H 0.5028 -0.3360 0.0506 0.205 Uiso 1 1 calc R
H13C H 0.5341 -0.2564 0.0779 0.205 Uiso 1 1 calc R
C22 C 0.3224(3) -0.35231(18) 0.1261(3) 0.190(2) Uani 1 1 d .
H11A H 0.2771 -0.3276 0.0940 0.284 Uiso 1 1 calc R
H11B H 0.2867 -0.3573 0.1690 0.284 Uiso 1 1 calc R
H11C H 0.3407 -0.4011 0.1091 0.284 Uiso 1 1 calc R
C23 C 0.4936(3) -0.3415(2) 0.1881(2) 0.1628(17) Uani 1 1 d .
H12A H 0.4553 -0.3505 0.2295 0.244 Uiso 1 1 calc R
H12B H 0.5512 -0.3081 0.1972 0.244 Uiso 1 1 calc R
H12C H 0.5203 -0.3881 0.1708 0.244 Uiso 1 1 calc R
N1 N 0.37282(11) -0.11605(9) 0.19331(8) 0.0607(4) Uani 1 1 d .
N2 N 0.25625(15) -0.06051(12) 0.07696(10) 0.0735(5) Uani 1 1 d .
O1 O 0.49974(11) -0.03012(10) 0.22840(8) 0.0884(5) Uani 1 1 d .
O2 O 0.53061(12) -0.17338(10) 0.17305(9) 0.0928(5) Uani 1 1 d .
O3 O 0.37658(12) -0.23559(8) 0.16373(9) 0.0851(5) Uani 1 1 d .
O4 O 0.36151(14) 0.05030(11) 0.02412(10) 0.1026(6) Uani 1 1 d .
H1 H 0.2317(14) -0.1565(11) 0.2145(10) 0.060(5) Uiso 1 1 d .
H2 H 0.2409(15) -0.1695(11) 0.0984(10) 0.067(6) Uiso 1 1 d .
H3 H 0.2797(17) -0.0256(13) 0.0967(11) 0.076(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 0.0033 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'
N N 0.0061 0.0033 '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
O1 C1 N1 125.9(2)
O1 C1 C2 128.6(2)
N1 C1 C2 105.54(16)
C3 C2 C1 110.7(2)
C2 C3 C4 111.53(18)
N1 C4 C3 101.78(15)
N1 C4 C5 112.88(15)
C3 C4 C5 113.13(17)
N2 C5 C6 113.26(17)
N2 C5 C4 109.02(16)
C6 C5 C4 111.12(15)
C7 C6 C11 117.6(2)
C7 C6 C5 119.9(2)
C11 C6 C5 122.50(19)
C6 C7 C8 120.9(3)
C9 C8 C7 120.0(3)
C10 C9 C8 119.9(3)
C9 C10 C11 120.4(3)
C6 C11 C10 121.2(2)
N2 C12 C13 122.9(2)
N2 C12 C17 116.9(2)
C13 C12 C17 120.2(2)
C12 C13 C14 119.0(3)
C15 C14 C13 119.1(3)
C16 C15 C14 122.4(3)
C15 C16 C17 120.4(3)
O4 C17 C16 126.7(3)
O4 C17 C12 114.5(2)
C16 C17 C12 118.8(3)
O2 C19 O3 126.5(2)
O2 C19 N1 124.7(2)
O3 C19 N1 108.80(18)
O3 C20 C23 109.5(3)
O3 C20 C21 109.4(2)
C23 C20 C21 112.4(3)
O3 C20 C22 100.8(2)
C23 C20 C22 111.5(3)
C21 C20 C22 112.6(3)
C19 N1 C1 124.57(17)
C19 N1 C4 124.92(17)
C1 N1 C4 110.33(16)
C12 N2 C5 123.5(2)
C19 O3 C20 121.61(18)
C17 O4 C18 117.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.207(2)
C1 N1 1.405(3)
C1 C2 1.445(3)
C2 C3 1.307(3)
C3 C4 1.477(3)
C4 N1 1.471(2)
C4 C5 1.540(3)
C5 N2 1.446(3)
C5 C6 1.520(3)
C6 C7 1.371(3)
C6 C11 1.381(3)
C7 C8 1.398(4)
C8 C9 1.360(5)
C9 C10 1.349(4)
C10 C11 1.384(3)
C12 N2 1.368(3)
C12 C13 1.376(3)
C12 C17 1.426(3)
C13 C14 1.427(4)
C14 C15 1.361(4)
C15 C16 1.355(4)
C16 C17 1.382(4)
C17 O4 1.342(3)
C18 O4 1.430(3)
C19 O2 1.195(2)
C19 O3 1.333(3)
C19 N1 1.383(3)
C20 O3 1.488(3)
C20 C23 1.512(5)
C20 C21 1.502(4)
C20 C22 1.512(4)
