#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/27/4022777.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_4022777
loop_
_publ_author_name
'Xiao-Ping Jiang'
'Ying Cheng'
'Gao-Feng Shi'
'Zhi-Mei Kang'
_publ_section_title
;
 A Versatile Strategy for Divergent and Diastereoselective
 Synthesis of Natural Product-Like Polyhydroxylated Indolizidines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2212
_journal_page_last               2215
_journal_paper_doi               10.1021/jo0624290
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C13 H19 N O6'
_chemical_formula_sum            'C13 H19 N O6'
_chemical_formula_weight         285.29
_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                   9.6256(19)
_cell_length_b                   9.795(2)
_cell_length_c                   14.391(3)
_cell_measurement_reflns_used    4032
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.5
_cell_volume                     1356.8(5)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_sigmaI/netI    0.0460
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17562
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.9890
_exptl_absorpt_correction_T_min  0.9760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'None, Friedel Pairs merged'
_refine_ls_extinction_coef       0.046(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         1926
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0364
_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)+(0.0611P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0876
_reflns_number_gt                1770
_reflns_number_total             1926
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0624290si20070116_102203.cif
_cod_data_source_block           shelxl
_cod_database_code               4022777
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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
O1 O 0.97027(15) -0.18696(12) -0.11464(9) 0.0215(3) Uani 1 1 d .
O2 O 1.03930(15) 0.28453(14) -0.19820(9) 0.0233(3) Uani 1 1 d .
H1 H 1.022(3) 0.285(2) -0.2613(18) 0.035 Uiso 1 1 d .
O3 O 1.01601(14) 0.45012(14) -0.00662(10) 0.0252(3) Uani 1 1 d .
O4 O 0.79336(13) 0.40290(12) -0.04096(9) 0.0195(3) Uani 1 1 d .
O5 O 0.96560(14) 0.15017(15) 0.14414(8) 0.0229(3) Uani 1 1 d .
O6 O 0.90069(16) -0.05564(14) 0.19798(9) 0.0283(3) Uani 1 1 d .
N1 N 0.88158(16) -0.01893(14) -0.02557(10) 0.0152(3) Uani 1 1 d .
C1 C 0.95047(19) -0.06353(18) -0.10043(12) 0.0171(4) Uani 1 1 d .
C2 C 1.0081(2) 0.04387(18) -0.16602(11) 0.0192(4) Uani 1 1 d .
H2A H 0.9871 0.0154 -0.2305 0.023 Uiso 1 1 calc R
H2B H 1.1104 0.0455 -0.1593 0.023 Uiso 1 1 calc R
C3 C 0.9538(2) 0.18871(17) -0.15234(11) 0.0174(4) Uani 1 1 d .
H3 H 0.8568 0.1955 -0.1768 0.021 Uiso 1 1 calc R
C4 C 0.95461(18) 0.21955(17) -0.04761(11) 0.0144(3) Uani 1 1 d .
H4 H 1.0480 0.1953 -0.0220 0.017 Uiso 1 1 calc R
C5 C 0.84677(18) 0.12524(18) -0.00467(12) 0.0154(4) Uani 1 1 d .
H5 H 0.7539 0.1467 -0.0321 0.018 Uiso 1 1 calc R
C6 C 0.83440(19) 0.12647(18) 0.10105(12) 0.0173(4) Uani 1 1 d .
H6 H 0.7624 0.1927 0.1228 0.021 Uiso 1 1 calc R
C7 C 0.7985(2) -0.02221(17) 0.12966(12) 0.0179(4) Uani 1 1 d .
H7 H 0.7022 -0.0292 0.1553 0.022 Uiso 1 1 calc R
C8 C 0.8167(2) -0.11055(18) 0.04277(12) 0.0178(4) Uani 1 1 d .
H8A H 0.8773 -0.1899 0.0558 0.021 Uiso 1 1 calc R
H8B H 0.7258 -0.1440 0.0200 0.021 Uiso 1 1 calc R
C9 C 0.9646(2) 0.0694(2) 0.22691(13) 0.0222(4) Uani 1 1 d .
C10 C 0.8811(2) 0.1372(2) 0.30331(12) 0.0252(4) Uani 1 1 d .
H10A H 0.9266 0.2225 0.3218 0.030 Uiso 1 1 calc R
H10B H 0.8753 0.0759 0.3570 0.030 Uiso 1 1 calc R
H10C H 0.7873 0.1571 0.2805 0.030 Uiso 1 1 calc R
C11 C 1.1125(2) 0.0408(3) 0.25679(15) 0.0382(6) Uani 1 1 d .
H11A H 1.1566 0.1261 0.2768 0.046 Uiso 1 1 calc R
H11B H 1.1645 0.0022 0.2045 0.046 Uiso 1 1 calc R
H11C H 1.1122 -0.0244 0.3085 0.046 Uiso 1 1 calc R
C12 C 0.92772(18) 0.36915(18) -0.02905(12) 0.0162(4) Uani 1 1 d .
C13 C 0.7623(2) 0.54692(18) -0.02818(13) 0.0216(4) Uani 1 1 d .
H13A H 0.6629 0.5625 -0.0382 0.026 Uiso 1 1 calc R
H13B H 0.8159 0.6010 -0.0729 0.026 Uiso 1 1 calc R
H13C H 0.7872 0.5743 0.0352 0.026 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 0.0033 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
C3 O2 H1 111.0(15)
C12 O4 C13 114.83(14)
C6 O5 C9 105.44(14)
C7 O6 C9 107.44(14)
C1 N1 C8 123.33(15)
C1 N1 C5 125.90(14)
C8 N1 C5 110.47(13)
O1 C1 N1 121.79(16)
O1 C1 C2 121.10(16)
N1 C1 C2 117.08(15)
C1 C2 C3 116.08(14)
C1 C2 H2A 108.3
C3 C2 H2A 108.3
C1 C2 H2B 108.3
C3 C2 H2B 108.3
H2A C2 H2B 107.4
O2 C3 C2 111.03(15)
O2 C3 C4 108.96(14)
C2 C3 C4 107.93(13)
O2 C3 H3 109.6
C2 C3 H3 109.6
C4 C3 H3 109.6
C12 C4 C5 113.58(14)
C12 C4 C3 111.28(13)
C5 C4 C3 106.01(14)
C12 C4 H4 108.6
C5 C4 H4 108.6
C3 C4 H4 108.6
N1 C5 C4 110.00(14)
N1 C5 C6 103.15(14)
C4 C5 C6 116.98(15)
N1 C5 H5 108.8
C4 C5 H5 108.8
C6 C5 H5 108.8
O5 C6 C5 111.45(14)
O5 C6 C7 103.55(15)
C5 C6 C7 105.92(14)
O5 C6 H6 111.8
C5 C6 H6 111.8
C7 C6 H6 111.8
O6 C7 C8 110.75(15)
O6 C7 C6 104.16(14)
C8 C7 C6 106.76(14)
O6 C7 H7 111.6
C8 C7 H7 111.6
C6 C7 H7 111.6
N1 C8 C7 104.46(13)
N1 C8 H8A 110.9
C7 C8 H8A 110.9
N1 C8 H8B 110.9
C7 C8 H8B 110.9
H8A C8 H8B 108.9
O5 C9 O6 103.53(14)
O5 C9 C11 109.44(17)
O6 C9 C11 109.17(18)
O5 C9 C10 111.42(15)
O6 C9 C10 110.98(16)
C11 C9 C10 111.96(16)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C9 C11 H11A 109.5
C9 C11 H11B 109.5
H11A C11 H11B 109.5
C9 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
O3 C12 O4 123.33(17)
O3 C12 C4 124.33(16)
O4 C12 C4 112.34(15)
O4 C13 H13A 109.5
O4 C13 H13B 109.5
H13A C13 H13B 109.5
O4 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.241(2)
O2 C3 1.412(2)
O2 H1 0.92(3)
O3 C12 1.206(2)
O4 C12 1.346(2)
O4 C13 1.454(2)
O5 C6 1.426(2)
O5 C9 1.430(2)
O6 C7 1.429(2)
O6 C9 1.432(2)
N1 C1 1.338(2)
N1 C8 1.471(2)
N1 C5 1.482(2)
C1 C2 1.518(2)
C2 C3 1.524(2)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.537(2)
C3 H3 1.0000
C4 C12 1.512(2)
C4 C5 1.521(2)
C4 H4 1.0000
C5 C6 1.526(2)
C5 H5 1.0000
C6 C7 1.552(2)
C6 H6 1.0000
C7 C8 1.531(2)
C7 H7 1.0000
C8 H8A 0.9900
C8 H8B 0.9900
C9 C11 1.513(3)
C9 C10 1.515(2)
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H1 O1 0.92(3) 1.81(3) 2.7094(19) 165(2) 3_754
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
C8 N1 C1 O1 -3.8(3)
C5 N1 C1 O1 -176.89(17)
C8 N1 C1 C2 178.27(15)
C5 N1 C1 C2 5.1(3)
O1 C1 C2 C3 168.45(17)
N1 C1 C2 C3 -13.6(2)
C1 C2 C3 O2 164.10(14)
C1 C2 C3 C4 44.7(2)
O2 C3 C4 C12 48.9(2)
C2 C3 C4 C12 169.51(14)
O2 C3 C4 C5 172.80(14)
C2 C3 C4 C5 -66.54(17)
C1 N1 C5 C4 -28.7(2)
C8 N1 C5 C4 157.40(14)
C1 N1 C5 C6 -154.22(17)
C8 N1 C5 C6 31.90(18)
C12 C4 C5 N1 -179.56(14)
C3 C4 C5 N1 57.94(17)
C12 C4 C5 C6 -62.4(2)
C3 C4 C5 C6 175.13(15)
C9 O5 C6 C5 -144.37(15)
C9 O5 C6 C7 -30.92(17)
N1 C5 C6 O5 87.47(17)
C4 C5 C6 O5 -33.4(2)
N1 C5 C6 C7 -24.49(17)
C4 C5 C6 C7 -145.35(15)
C9 O6 C7 C8 129.35(15)
C9 O6 C7 C6 14.92(18)
O5 C6 C7 O6 9.80(17)
C5 C6 C7 O6 127.19(15)
O5 C6 C7 C8 -107.42(16)
C5 C6 C7 C8 9.96(19)
C1 N1 C8 C7 160.25(16)
C5 N1 C8 C7 -25.68(19)
O6 C7 C8 N1 -104.02(16)
C6 C7 C8 N1 8.8(2)
C6 O5 C9 O6 40.91(18)
C6 O5 C9 C11 157.22(17)
C6 O5 C9 C10 -78.42(18)
C7 O6 C9 O5 -34.37(18)
C7 O6 C9 C11 -150.86(16)
C7 O6 C9 C10 85.27(18)
C13 O4 C12 O3 2.3(2)
C13 O4 C12 C4 -177.33(13)
C5 C4 C12 O3 136.15(18)
C3 C4 C12 O3 -104.3(2)
C5 C4 C12 O4 -44.3(2)
C3 C4 C12 O4 75.27(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21194128
