#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:02:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178417 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/38/4023808.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_4023808
loop_
_publ_author_name
'Vincenzo Giulio Albano'
'Andrea Gualandi'
'Magda Monari'
'Diego Savoia'
_publ_section_title
;
 Asymmetric Synthesis of 8-Aminoindolizidine
 from Chiral 2-Pyrroleimines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8376
_journal_page_last               8381
_journal_paper_doi               10.1021/jo8014598
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C17 H28 N2 O2'
_chemical_formula_weight         292.41
_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                 106.953(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.5507(10)
_cell_length_b                   26.882(4)
_cell_length_c                   9.8409(14)
_cell_measurement_temperature    296(2)
_cell_volume                     1657.6(4)
_computing_cell_refinement       SMART
_computing_data_collection       SMART
_computing_data_reduction        SAINT+
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2004)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-97 (Giacovazzo, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART Apex II CCD'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0191
_diffrn_reflns_av_sigmaI/netI    0.0178
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13284
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.101
_refine_diff_density_rms         0.022
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.880
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         3681
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      0.879
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0365
_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)+(0.0465P)²+0.3157P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0900
_reflns_number_gt                3271
_reflns_number_total             3681
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8014598_si_002.cif
_cod_data_source_block           (S,R)-14b
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4023808
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
O10 O 1.4068(3) 0.67522(8) 0.5723(2) 0.0742(6) Uani 1 1 d . . .
O11 O 1.1170(3) 0.68394(7) 0.38543(18) 0.0649(5) Uani 1 1 d . . .
N4 N 1.0542(3) 0.67849(7) 0.96846(17) 0.0448(4) Uani 1 1 d . . .
N9 N 1.0823(3) 0.69707(7) 0.59934(18) 0.0439(4) Uani 1 1 d . . .
C1 C 0.8777(4) 0.62989(9) 0.7770(2) 0.0514(5) Uani 1 1 d . . .
H1A H 0.9866 0.6062 0.7714 0.062 Uiso 1 1 calc R . .
H1B H 0.7657 0.6302 0.6872 0.062 Uiso 1 1 calc R . .
C2 C 0.7881(5) 0.61748(12) 0.8999(3) 0.0743(8) Uani 1 1 d . . .
H2A H 0.6336 0.6195 0.8696 0.089 Uiso 1 1 calc R . .
H2B H 0.8300 0.5842 0.9354 0.089 Uiso 1 1 calc R . .
C3 C 0.8818(4) 0.65576(11) 1.0127(3) 0.0593(6) Uani 1 1 d . . .
H3A H 0.7757 0.6804 1.0171 0.071 Uiso 1 1 calc R . .
H3B H 0.9363 0.6402 1.1051 0.071 Uiso 1 1 calc R . .
C5 C 1.1326(5) 0.72546(10) 1.0347(3) 0.0600(6) Uani 1 1 d . . .
H5A H 1.1822 0.7214 1.1371 0.072 Uiso 1 1 calc R . .
H5B H 1.0184 0.7498 1.0124 0.072 Uiso 1 1 calc R . .
C6 C 1.3136(4) 0.74335(11) 0.9813(3) 0.0662(7) Uani 1 1 d . . .
H6A H 1.4338 0.7209 1.0138 0.079 Uiso 1 1 calc R . .
H6B H 1.3589 0.7760 1.0205 0.079 Uiso 1 1 calc R . .
C7 C 1.2476(4) 0.74615(10) 0.8196(3) 0.0605(6) Uani 1 1 d . . .
H7A H 1.3713 0.7539 0.7881 0.073 Uiso 1 1 calc R . .
H7B H 1.1439 0.7726 0.7875 0.073 Uiso 1 1 calc R . .
C8 C 1.1510(3) 0.69680(8) 0.7545(2) 0.0426(5) Uani 1 1 d D . .
H8 H 1.2632 0.6716 0.7843 0.051 Uiso 1 1 calc RD . .
C81 C 0.9717(3) 0.68129(8) 0.8141(2) 0.0395(4) Uani 1 1 d D . .
H81 H 0.8573 0.7061 0.7880 0.047 Uiso 1 1 calc RD . .
C10 C 1.2194(4) 0.68466(9) 0.5265(3) 0.0520(5) Uani 1 1 d . . .
C12 C 0.8920(4) 0.68862(11) 0.3667(3) 0.0623(6) Uani 1 1 d . . .
H12A H 0.8233 0.6563 0.3507 0.075 Uiso 1 1 calc R . .
H12B H 0.8261 0.7099 0.2863 0.075 Uiso 1 1 calc R . .
C13 C 0.8733(3) 0.71166(9) 0.5047(2) 0.0456(5) Uani 1 1 d D . .
H13 H 0.7604 0.6947 0.5338 0.055 Uiso 1 1 calc RD . .
C14 C 0.8306(3) 0.76767(9) 0.4962(2) 0.0470(5) Uani 1 1 d D . .
H14 H 0.8343 0.7783 0.5921 0.056 Uiso 1 1 calc RD . .
C15 C 0.9948(4) 0.79858(10) 0.4543(3) 0.0603(6) Uani 1 1 d . . .
H15A H 1.0010 0.7883 0.3612 0.072 Uiso 1 1 calc R . .
H15B H 1.1340 0.7929 0.5215 0.072 Uiso 1 1 calc R . .
C16 C 0.9426(6) 0.85348(12) 0.4510(4) 0.0848(10) Uani 1 1 d . . .
H16A H 1.0466 0.8720 0.4186 0.102 Uiso 1 1 calc R . .
H16B H 0.9517 0.8646 0.5464 0.102 Uiso 1 1 calc R . .
C17 C 0.7202(6) 0.86402(13) 0.3533(5) 0.0972(12) Uani 1 1 d . . .
H17A H 0.7153 0.8562 0.2562 0.117 Uiso 1 1 calc R . .
H17B H 0.6881 0.8991 0.3576 0.117 Uiso 1 1 calc R . .
C18 C 0.5545(5) 0.83351(14) 0.3957(4) 0.0870(10) Uani 1 1 d . . .
H18A H 0.5474 0.8443 0.4882 0.104 Uiso 1 1 calc R . .
H18B H 0.4157 0.8391 0.3278 0.104 Uiso 1 1 calc R . .
C19 C 0.6062(4) 0.77869(12) 0.4012(3) 0.0672(7) Uani 1 1 d . . .
H19A H 0.5930 0.7669 0.3058 0.081 Uiso 1 1 calc R . .
H19B H 0.5037 0.7607 0.4364 0.081 Uiso 1 1 calc R . .
O10B O 0.7487(3) 0.52009(8) 0.1079(2) 0.0734(6) Uani 1 1 d . . .
O11B O 0.5829(3) 0.58242(7) 0.1849(2) 0.0669(5) Uani 1 1 d . . .
N4B N 0.1884(3) 0.38543(7) 0.0238(2) 0.0573(5) Uani 1 1 d . . .
N9B N 0.4297(3) 0.50850(7) 0.1552(2) 0.0494(4) Uani 1 1 d . . .
C1B C 0.0473(4) 0.46108(10) -0.0694(3) 0.0618(6) Uani 1 1 d . . .
H1C H 0.1284 0.4686 -0.1350 0.074 Uiso 1 1 calc R . .
H1D H -0.0181 0.4914 -0.0487 0.074 Uiso 1 1 calc R . .
C2B C -0.1207(5) 0.42121(13) -0.1298(4) 0.0787(8) Uani 1 1 d . . .
H2C H -0.2561 0.4302 -0.1152 0.094 Uiso 1 1 calc R . .
H2D H -0.1413 0.4168 -0.2308 0.094 Uiso 1 1 calc R . .
C3B C -0.0329(5) 0.37401(12) -0.0490(4) 0.0764(8) Uani 1 1 d . . .
H3C H -0.1100 0.3658 0.0185 0.092 Uiso 1 1 calc R . .
H3D H -0.0432 0.3463 -0.1137 0.092 Uiso 1 1 calc R . .
C5B C 0.2925(5) 0.35282(10) 0.1405(3) 0.0725(8) Uani 1 1 d . . .
H5C H 0.2844 0.3187 0.1072 0.087 Uiso 1 1 calc R . .
H5D H 0.2209 0.3548 0.2138 0.087 Uiso 1 1 calc R . .
C6B C 0.5226(5) 0.36796(11) 0.2007(4) 0.0785(9) Uani 1 1 d . . .
H6C H 0.5975 0.3621 0.1305 0.094 Uiso 1 1 calc R . .
H6D H 0.5892 0.3477 0.2833 0.094 Uiso 1 1 calc R . .
C7B C 0.5418(4) 0.42275(10) 0.2431(3) 0.0674(7) Uani 1 1 d . . .
H7C H 0.4884 0.4276 0.3243 0.081 Uiso 1 1 calc R . .
H7D H 0.6908 0.4325 0.2704 0.081 Uiso 1 1 calc R . .
C8B C 0.4155(4) 0.45527(9) 0.1202(3) 0.0514(5) Uani 1 1 d D . .
H8B H 0.4800 0.4508 0.0428 0.062 Uiso 1 1 calc RD . .
C81B C 0.1875(4) 0.43765(8) 0.0652(2) 0.0463(5) Uani 1 1 d D . .
H81B H 0.1182 0.4407 0.1406 0.056 Uiso 1 1 calc RD . .
C10B C 0.5985(4) 0.53482(10) 0.1444(3) 0.0545(6) Uani 1 1 d . . .
C12B C 0.3746(4) 0.58936(10) 0.2025(3) 0.0636(7) Uani 1 1 d . . .
H12C H 0.2800 0.6054 0.1195 0.076 Uiso 1 1 calc R . .
H12D H 0.3828 0.6097 0.2853 0.076 Uiso 1 1 calc R . .
C13B C 0.2940(3) 0.53710(8) 0.2215(3) 0.0492(5) Uani 1 1 d D . .
H13B H 0.1448 0.5339 0.1640 0.059 Uiso 1 1 calc RD . .
C14B C 0.3137(3) 0.52243(9) 0.3740(3) 0.0487(5) Uani 1 1 d D . .
H14B H 0.2872 0.4865 0.3720 0.058 Uiso 1 1 calc RD . .
C15B C 0.1434(4) 0.54575(12) 0.4281(3) 0.0701(8) Uani 1 1 d . . .
H15C H 0.1604 0.5816 0.4300 0.084 Uiso 1 1 calc R . .
H15D H 0.0044 0.5380 0.3633 0.084 Uiso 1 1 calc R . .
C16B C 0.1521(5) 0.52782(15) 0.5746(3) 0.0834(9) Uani 1 1 d . . .
H16C H 0.1180 0.4926 0.5709 0.100 Uiso 1 1 calc R . .
H16D H 0.0463 0.5454 0.6075 0.100 Uiso 1 1 calc R . .
C17B C 0.3706(5) 0.53612(16) 0.6781(3) 0.0889(10) Uani 1 1 d . . .
H17C H 0.3965 0.5716 0.6916 0.107 Uiso 1 1 calc R . .
H17D H 0.3749 0.5217 0.7693 0.107 Uiso 1 1 calc R . .
C18B C 0.5428(5) 0.51328(13) 0.6262(3) 0.0745(8) Uani 1 1 d . . .
H18C H 0.5297 0.4774 0.6273 0.089 Uiso 1 1 calc R . .
H18D H 0.6807 0.5222 0.6906 0.089 Uiso 1 1 calc R . .
C19B C 0.5335(4) 0.52991(10) 0.4775(3) 0.0572(6) Uani 1 1 d . . .
H19C H 0.5716 0.5648 0.4794 0.069 Uiso 1 1 calc R . .
H19D H 0.6371 0.5112 0.4451 0.069 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 0.0016 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O11 C12 108.25(17) . . ?
C5 N4 C81 113.58(18) . . ?
C5 N4 C3 115.84(19) . . ?
C81 N4 C3 104.38(17) . . ?
C10 N9 C8 120.40(18) . . ?
C10 N9 C13 111.86(18) . . ?
C8 N9 C13 127.69(17) . . ?
C81 C1 C2 103.4(2) . . ?
C3 C2 C1 105.4(2) . . ?
N4 C3 C2 104.55(19) . . ?
N4 C5 C6 109.5(2) . . ?
C5 C6 C7 111.5(2) . . ?
C6 C7 C8 110.6(2) . . ?
N9 C8 C81 111.64(16) . . ?
N9 C8 C7 113.43(18) . . ?
C81 C8 C7 110.44(18) . . ?
N4 C81 C8 108.90(16) . . ?
N4 C81 C1 101.86(17) . . ?
C8 C81 C1 117.65(18) . . ?
O10 C10 N9 128.2(2) . . ?
O10 C10 O11 121.8(2) . . ?
N9 C10 O11 110.0(2) . . ?
O11 C12 C13 105.45(19) . . ?
N9 C13 C12 98.85(18) . . ?
N9 C13 C14 114.81(18) . . ?
C12 C13 C14 114.27(19) . . ?
C15 C14 C19 111.2(2) . . ?
C15 C14 C13 115.07(19) . . ?
C19 C14 C13 110.7(2) . . ?
C14 C15 C16 111.6(2) . . ?
C15 C16 C17 111.4(3) . . ?
C16 C17 C18 110.9(3) . . ?
C19 C18 C17 111.6(3) . . ?
C18 C19 C14 112.2(3) . . ?
C10B O11B C12B 108.30(18) . . ?
C3B N4B C5B 115.8(2) . . ?
C3B N4B C81B 104.9(2) . . ?
C5B N4B C81B 113.5(2) . . ?
C10B N9B C13B 112.3(2) . . ?
C10B N9B C8B 119.5(2) . . ?
C13B N9B C8B 127.66(18) . . ?
C81B C1B C2B 103.5(2) . . ?
C3B C2B C1B 105.2(2) . . ?
N4B C3B C2B 104.7(2) . . ?
N4B C5B C6B 109.5(2) . . ?
C5B C6B C7B 111.2(2) . . ?
C8B C7B C6B 110.7(2) . . ?
N9B C8B C81B 112.24(18) . . ?
N9B C8B C7B 112.9(2) . . ?
C81B C8B C7B 110.8(2) . . ?
N4B C81B C8B 108.52(18) . . ?
N4B C81B C1B 101.9(2) . . ?
C8B C81B C1B 117.9(2) . . ?
O10B C10B O11B 122.4(2) . . ?
O10B C10B N9B 127.7(3) . . ?
O11B C10B N9B 109.9(2) . . ?
O11B C12B C13B 105.59(19) . . ?
N9B C13B C14B 114.59(18) . . ?
N9B C13B C12B 98.74(19) . . ?
C14B C13B C12B 115.2(2) . . ?
C15B C14B C19B 111.4(2) . . ?
C15B C14B C13B 112.5(2) . . ?
C19B C14B C13B 114.76(19) . . ?
C16B C15B C14B 112.3(3) . . ?
C15B C16B C17B 111.2(3) . . ?
C18B C17B C16B 111.6(3) . . ?
C17B C18B C19B 112.7(3) . . ?
C14B C19B C18B 111.9(2) . . ?
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
O10 C10 1.205(3) . ?
O11 C10 1.354(3) . ?
O11 C12 1.437(3) . ?
N4 C5 1.445(3) . ?
N4 C81 1.458(2) . ?
N4 C3 1.457(3) . ?
N9 C10 1.345(3) . ?
N9 C8 1.460(3) . ?
N9 C13 1.467(3) . ?
C1 C81 1.513(3) . ?
C1 C2 1.527(3) . ?
C2 C3 1.507(4) . ?
C5 C6 1.509(4) . ?
C6 C7 1.525(3) . ?
C7 C8 1.528(3) . ?
C8 C81 1.516(3) . ?
C12 C13 1.530(3) . ?
C13 C14 1.529(3) . ?
C14 C15 1.508(3) . ?
C14 C19 1.524(3) . ?
C15 C16 1.513(4) . ?
C16 C17 1.520(5) . ?
C17 C18 1.513(5) . ?
C18 C19 1.509(5) . ?
O10B C10B 1.208(3) . ?
O11B C10B 1.353(3) . ?
O11B C12B 1.437(3) . ?
N4B C3B 1.450(4) . ?
N4B C5B 1.448(4) . ?
N4B C81B 1.462(3) . ?
N9B C10B 1.343(3) . ?
N9B C13B 1.464(3) . ?
N9B C8B 1.468(3) . ?
C1B C81B 1.512(3) . ?
C1B C2B 1.527(4) . ?
C2B C3B 1.519(5) . ?
C5B C6B 1.506(4) . ?
C6B C7B 1.526(4) . ?
C7B C8B 1.526(4) . ?
C8B C81B 1.508(3) . ?
C12B C13B 1.531(3) . ?
C13B C14B 1.521(3) . ?
C14B C15B 1.506(3) . ?
C14B C19B 1.515(3) . ?
C15B C16B 1.505(5) . ?
C16B C17B 1.512(4) . ?
C17B C18B 1.499(5) . ?
C18B C19B 1.514(4) . ?
