#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:02:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178417 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/38/4023809.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_4023809
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            'C14 H24 N2 O2'
_chemical_formula_weight         252.35
_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            8
_cell_length_a                   5.8590(4)
_cell_length_b                   14.2547(9)
_cell_length_c                   33.866(2)
_cell_measurement_temperature    296(2)
_cell_volume                     2828.5(3)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0151
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            23702
_diffrn_reflns_theta_full        27.74
_diffrn_reflns_theta_max         27.74
_diffrn_reflns_theta_min         1.55
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.5(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         3803
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0401
_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)+(0.0561P)²+0.2279P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1098
_reflns_number_gt                3208
_reflns_number_total             3803
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8014598_si_003.cif
_cod_data_source_block           (S,S)-14a
_cod_database_code               4023809
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O11 O 0.8314(4) 0.27100(11) 0.83612(6) 0.0843(5) Uani 1 1 d . . .
O10 O 0.5183(4) 0.27597(16) 0.79766(7) 0.1133(8) Uani 1 1 d . . .
C1 C 0.8477(6) 0.3976(3) 0.72920(8) 0.1043(11) Uani 1 1 d . . .
H1A H 0.7436 0.3680 0.7108 0.125 Uiso 1 1 calc R . .
H1B H 0.8900 0.3524 0.7493 0.125 Uiso 1 1 calc R . .
C2 C 1.0602(7) 0.4350(3) 0.70770(9) 0.1194(13) Uani 1 1 d . . .
H2A H 1.1978 0.4059 0.7179 0.143 Uiso 1 1 calc R . .
H2B H 1.0503 0.4232 0.6795 0.143 Uiso 1 1 calc R . .
C3 C 1.0586(6) 0.5383(3) 0.71616(8) 0.1007(11) Uani 1 1 d . . .
H3A H 1.2127 0.5622 0.7191 0.121 Uiso 1 1 calc R . .
H3B H 0.9827 0.5726 0.6952 0.121 Uiso 1 1 calc R . .
C5 C 0.8599(7) 0.6403(2) 0.76221(9) 0.1015(10) Uani 1 1 d . . .
H5A H 0.7613 0.6637 0.7414 0.122 Uiso 1 1 calc R . .
H5B H 0.9915 0.6814 0.7640 0.122 Uiso 1 1 calc R . .
C6 C 0.7312(6) 0.64005(19) 0.80140(9) 0.0953(10) Uani 1 1 d . . .
H6A H 0.6696 0.7021 0.8063 0.114 Uiso 1 1 calc R . .
H6B H 0.8364 0.6252 0.8226 0.114 Uiso 1 1 calc R . .
C7 C 0.5366(5) 0.5686(2) 0.80121(8) 0.0885(9) Uani 1 1 d . . .
H7A H 0.4797 0.5617 0.8280 0.106 Uiso 1 1 calc R . .
H7B H 0.4129 0.5931 0.7852 0.106 Uiso 1 1 calc R . .
C8 C 0.6018(4) 0.47228(19) 0.78565(6) 0.0673(6) Uani 1 1 d D . .
H8 H 0.457(4) 0.4409(16) 0.7796(8) 0.081 Uiso 1 1 d D . .
C81 C 0.7401(4) 0.4831(2) 0.74752(6) 0.0767(8) Uani 1 1 d D . .
H81 H 0.630(4) 0.5114(19) 0.7295(7) 0.092 Uiso 1 1 d D . .
C10 C 0.6739(5) 0.3157(2) 0.81410(7) 0.0756(8) Uani 1 1 d . . .
C12 C 1.0104(5) 0.33567(15) 0.84499(8) 0.0700(6) Uani 1 1 d . . .
H12A H 1.1373 0.3275 0.8269 0.084 Uiso 1 1 calc R . .
H12B H 1.0647 0.3267 0.8718 0.084 Uiso 1 1 calc R . .
C13 C 0.9051(4) 0.43259(13) 0.84019(5) 0.0482(4) Uani 1 1 d D . .
H13 H 1.013(3) 0.4734(13) 0.8274(6) 0.058 Uiso 1 1 d D . .
C14 C 0.8315(4) 0.47686(15) 0.87940(6) 0.0573(5) Uani 1 1 d D . .
H14 H 0.758(4) 0.5363(12) 0.8735(7) 0.069 Uiso 1 1 d D . .
C15 C 1.0412(6) 0.5055(2) 0.90316(8) 0.0894(9) Uani 1 1 d . . .
H15A H 0.9949 0.5432 0.9253 0.134 Uiso 1 1 calc R . .
H15B H 1.1426 0.5411 0.8867 0.134 Uiso 1 1 calc R . .
H15C H 1.1182 0.4504 0.9125 0.134 Uiso 1 1 calc R . .
C16 C 0.6734(5) 0.4144(2) 0.90370(7) 0.0776(7) Uani 1 1 d . . .
H16A H 0.7561 0.3604 0.9128 0.116 Uiso 1 1 calc R . .
H16B H 0.5474 0.3946 0.8876 0.116 Uiso 1 1 calc R . .
H16C H 0.6171 0.4490 0.9260 0.116 Uiso 1 1 calc R . .
N4 N 0.9330(4) 0.54633(16) 0.75296(5) 0.0696(6) Uani 1 1 d . . .
N9 N 0.7132(3) 0.41010(12) 0.81426(5) 0.0549(4) Uani 1 1 d . . .
N4B N 0.2995(3) 1.11489(9) 0.92484(4) 0.0401(3) Uani 1 1 d . . .
N9B N 0.5627(3) 0.93143(10) 0.94931(4) 0.0490(4) Uani 1 1 d . . .
O10B O 0.7787(4) 0.92398(15) 1.00621(5) 0.0918(6) Uani 1 1 d . . .
O11B O 0.4654(4) 0.83547(13) 0.99790(5) 0.0903(7) Uani 1 1 d . . .
C1B C 0.4050(4) 1.10339(13) 0.99100(5) 0.0499(5) Uani 1 1 d . . .
H1C H 0.5131 1.1291 1.0098 0.060 Uiso 1 1 calc R . .
H1D H 0.3651 1.0401 0.9990 0.060 Uiso 1 1 calc R . .
C2B C 0.1924(4) 1.16516(15) 0.98811(6) 0.0604(5) Uani 1 1 d . . .
H2C H 0.0580 1.1313 0.9969 0.072 Uiso 1 1 calc R . .
H2D H 0.2095 1.2213 1.0040 0.072 Uiso 1 1 calc R . .
C3B C 0.1740(4) 1.18983(12) 0.94450(6) 0.0522(5) Uani 1 1 d . . .
H3C H 0.0159 1.1909 0.9360 0.063 Uiso 1 1 calc R . .
H3D H 0.2426 1.2504 0.9391 0.063 Uiso 1 1 calc R . .
C5B C 0.3577(4) 1.13424(12) 0.88386(5) 0.0515(5) Uani 1 1 d . . .
H5C H 0.4493 1.1908 0.8823 0.062 Uiso 1 1 calc R . .
H5D H 0.2196 1.1440 0.8686 0.062 Uiso 1 1 calc R . .
C6B C 0.4900(4) 1.05226(14) 0.86709(5) 0.0557(5) Uani 1 1 d . . .
H6C H 0.5378 1.0670 0.8404 0.067 Uiso 1 1 calc R . .
H6D H 0.3914 0.9977 0.8659 0.067 Uiso 1 1 calc R . .
C7B C 0.6986(4) 1.02947(14) 0.89193(6) 0.0543(5) Uani 1 1 d . . .
H7C H 0.8127 1.0777 0.8876 0.065 Uiso 1 1 calc R . .
H7D H 0.7622 0.9705 0.8829 0.065 Uiso 1 1 calc R . .
C8B C 0.6526(3) 1.02203(13) 0.93644(5) 0.0448(4) Uani 1 1 d D . .
H8B H 0.802(3) 1.0279(14) 0.9490(6) 0.054 Uiso 1 1 d D . .
C81B C 0.5038(3) 1.10423(11) 0.94929(5) 0.0405(4) Uani 1 1 d D . .
H81B H 0.598(3) 1.1611(12) 0.9447(6) 0.049 Uiso 1 1 d D . .
C10B C 0.6180(5) 0.90056(17) 0.98592(7) 0.0680(7) Uani 1 1 d . . .
C12B C 0.2764(5) 0.83526(18) 0.97114(9) 0.0831(9) Uani 1 1 d . . .
H12C H 0.1493 0.8705 0.9820 0.100 Uiso 1 1 calc R . .
H12D H 0.2264 0.7716 0.9658 0.100 Uiso 1 1 calc R . .
C13B C 0.3654(4) 0.88153(13) 0.93363(7) 0.0548(5) Uani 1 1 d D . .
H13B H 0.254(4) 0.9236(14) 0.9240(6) 0.066 Uiso 1 1 d D . .
C14B C 0.4285(4) 0.81148(14) 0.90092(7) 0.0646(6) Uani 1 1 d D . .
H14B H 0.514(4) 0.8483(16) 0.8814(6) 0.077 Uiso 1 1 d D . .
C15B C 0.2129(6) 0.7715(2) 0.88193(11) 0.1025(10) Uani 1 1 d . . .
H15D H 0.1297 0.7356 0.9011 0.154 Uiso 1 1 calc R . .
H15E H 0.2544 0.7317 0.8602 0.154 Uiso 1 1 calc R . .
H15F H 0.1191 0.8220 0.8725 0.154 Uiso 1 1 calc R . .
C16B C 0.5839(5) 0.73313(17) 0.91539(10) 0.0892(8) Uani 1 1 d . . .
H16D H 0.5027 0.6946 0.9339 0.134 Uiso 1 1 calc R . .
H16E H 0.7155 0.7598 0.9280 0.134 Uiso 1 1 calc R . .
H16F H 0.6317 0.6956 0.8934 0.134 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 108.33(17) . . ?
C81 C1 C2 104.7(3) . . ?
C3 C2 C1 104.1(3) . . ?
N4 C3 C2 104.1(2) . . ?
N4 C5 C6 109.5(2) . . ?
C5 C6 C7 111.5(3) . . ?
C8 C7 C6 114.6(2) . . ?
N9 C8 C7 115.39(19) . . ?
N9 C8 C81 112.4(2) . . ?
C7 C8 C81 109.6(2) . . ?
N4 C81 C1 103.2(2) . . ?
N4 C81 C8 111.5(2) . . ?
C1 C81 C8 119.2(2) . . ?
O10 C10 O11 123.4(3) . . ?
O10 C10 N9 126.2(3) . . ?
O11 C10 N9 110.4(2) . . ?
O11 C12 C13 105.43(19) . . ?
N9 C13 C12 100.18(17) . . ?
N9 C13 C14 113.23(18) . . ?
C12 C13 C14 113.28(17) . . ?
C15 C14 C16 111.16(19) . . ?
C15 C14 C13 109.9(2) . . ?
C16 C14 C13 113.47(19) . . ?
C5 N4 C3 114.2(2) . . ?
C5 N4 C81 111.9(2) . . ?
C3 N4 C81 103.6(2) . . ?
C10 N9 C13 110.4(2) . . ?
C10 N9 C8 121.2(2) . . ?
C13 N9 C8 127.34(17) . . ?
C5B N4B C3B 114.51(14) . . ?
C5B N4B C81B 111.56(15) . . ?
C3B N4B C81B 103.31(14) . . ?
C10B N9B C8B 118.27(19) . . ?
C10B N9B C13B 111.37(19) . . ?
C8B N9B C13B 127.50(16) . . ?
C10B O11B C12B 108.87(17) . . ?
C81B C1B C2B 104.19(15) . . ?
C3B C2B C1B 104.64(16) . . ?
N4B C3B C2B 103.79(15) . . ?
N4B C5B C6B 109.37(14) . . ?
C5B C6B C7B 111.68(16) . . ?
C6B C7B C8B 114.67(17) . . ?
N9B C8B C81B 112.84(14) . . ?
N9B C8B C7B 114.65(15) . . ?
C81B C8B C7B 109.13(16) . . ?
N4B C81B C1B 102.38(15) . . ?
N4B C81B C8B 112.72(13) . . ?
C1B C81B C8B 118.36(15) . . ?
O10B C10B O11B 122.2(2) . . ?
O10B C10B N9B 127.9(3) . . ?
O11B C10B N9B 109.9(2) . . ?
O11B C12B C13B 105.2(2) . . ?
N9B C13B C12B 100.3(2) . . ?
N9B C13B C14B 112.90(18) . . ?
C12B C13B C14B 113.71(18) . . ?
C16B C14B C15B 110.9(2) . . ?
C16B C14B C13B 112.9(2) . . ?
C15B C14B C13B 110.3(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
O11 C10 1.346(4) . ?
O11 C12 1.428(3) . ?
O10 C10 1.209(3) . ?
C1 C81 1.505(5) . ?
C1 C2 1.537(4) . ?
C2 C3 1.501(5) . ?
C3 N4 1.451(3) . ?
C5 N4 1.441(4) . ?
C5 C6 1.526(4) . ?
C6 C7 1.530(4) . ?
C7 C8 1.519(4) . ?
C8 N9 1.466(3) . ?
C8 C81 1.532(3) . ?
C81 N4 1.458(3) . ?
C10 N9 1.366(3) . ?
C12 C13 1.522(3) . ?
C13 N9 1.462(3) . ?
C13 C14 1.532(3) . ?
C14 C15 1.525(3) . ?
C14 C16 1.526(3) . ?
N4B C5B 1.456(2) . ?
N4B C3B 1.458(2) . ?
N4B C81B 1.463(2) . ?
N9B C10B 1.355(3) . ?
N9B C8B 1.461(2) . ?
N9B C13B 1.457(3) . ?
O10B C10B 1.213(3) . ?
O11B C10B 1.351(3) . ?
O11B C12B 1.431(4) . ?
C1B C81B 1.527(2) . ?
C1B C2B 1.529(3) . ?
C2B C3B 1.522(3) . ?
C5B C6B 1.513(3) . ?
C6B C7B 1.519(3) . ?
C7B C8B 1.535(2) . ?
C8B C81B 1.524(2) . ?
C12B C13B 1.523(3) . ?
C13B C14B 1.537(3) . ?
C14B C16B 1.522(4) . ?
C14B C15B 1.528(4) . ?
