#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/34/1513441.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_1513441
loop_
_publ_author_name
'Kapras, Vojtěch'
'Pohl, Radek'
'Císařová, Ivana'
'Jahn, Ullrich'
_publ_section_title
;
 Asymmetric Domino Aza-Michael Addition/[3 + 2] Cycloaddition Reactions as
 a Versatile Approach to α,β,γ-Triamino Acid Derivatives.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              1088
_journal_page_last               1091
_journal_paper_doi               10.1021/ol403660w
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration syn
_chemical_compound_source        'synthesized by the authors'
_chemical_formula_moiety         'C20 H29 N3 O2'
_chemical_formula_sum            'C20 H29 N3 O2'
_chemical_formula_weight         343.46
_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   difmap
_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                   10.1265(2)
_cell_length_b                   10.6178(2)
_cell_length_c                   18.0640(3)
_cell_measurement_reflns_used    7754
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.22
_cell_volume                     1942.26(6)
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_collection       'Bruker Instrument Service v2012.12.0.0'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15309
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9813
_exptl_absorpt_correction_T_min  0.9496
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         4454
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0341
_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)+(0.0473P)²+0.1949P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0847
_reflns_number_gt                4057
_reflns_number_total             4454
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ol403660w_si_003.cif
_cod_data_source_block           vk_703_ii_jahn_uochb
_cod_database_code               1513441
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
N1 N 1.03509(10) 0.33954(9) -0.03913(6) 0.0252(2) Uani 1 1 d .
N2 N 0.98376(12) 0.27429(10) -0.08850(6) 0.0315(3) Uani 1 1 d .
N3 N 0.94673(9) 0.60020(9) -0.01100(5) 0.0203(2) Uani 1 1 d .
C1 C 0.93394(11) 0.37826(11) 0.01834(6) 0.0207(2) Uani 1 1 d .
C2 C 0.83933(15) 0.25752(12) -0.07587(8) 0.0330(3) Uani 1 1 d .
H2A H 0.8207 0.1751 -0.0525 0.040 Uiso 1 1 calc R
H2B H 0.7899 0.2632 -0.1230 0.040 Uiso 1 1 calc R
C3 C 0.80272(12) 0.36538(11) -0.02432(7) 0.0246(3) Uani 1 1 d .
H3 H 0.7282 0.3420 0.0093 0.029 Uiso 1 1 calc R
C4 C 0.77042(12) 0.48318(12) -0.06992(7) 0.0272(3) Uani 1 1 d .
H4A H 0.8189 0.4792 -0.1175 0.033 Uiso 1 1 calc R
H4B H 0.6748 0.4839 -0.0813 0.033 Uiso 1 1 calc R
C5 C 0.80612(11) 0.60379(11) -0.03056(7) 0.0237(3) Uani 1 1 d .
H5A H 0.7883 0.6768 -0.0632 0.028 Uiso 1 1 calc R
H5B H 0.7520 0.6129 0.0148 0.028 Uiso 1 1 calc R
C6 C 0.96734(11) 0.50977(11) 0.04930(6) 0.0211(2) Uani 1 1 d .
H6 H 0.9050 0.5298 0.0906 0.025 Uiso 1 1 calc R
C7 C 0.93894(12) 0.27492(11) 0.07809(7) 0.0229(2) Uani 1 1 d .
C8 C 1.10834(12) 0.51103(12) 0.07913(7) 0.0286(3) Uani 1 1 d .
H8A H 1.1707 0.5047 0.0378 0.043 Uiso 1 1 calc R
H8B H 1.1210 0.4394 0.1126 0.043 Uiso 1 1 calc R
H8C H 1.1239 0.5897 0.1061 0.043 Uiso 1 1 calc R
C9 C 1.00198(12) 0.72749(10) -0.00076(6) 0.0234(2) Uani 1 1 d .
H9 H 1.0934 0.7158 0.0191 0.028 Uiso 1 1 calc R
C10 C 0.92801(16) 0.80804(13) 0.05605(7) 0.0341(3) Uani 1 1 d .
H10A H 0.8421 0.8327 0.0358 0.051 Uiso 1 1 calc R
H10B H 0.9798 0.8836 0.0672 0.051 Uiso 1 1 calc R
H10C H 0.9148 0.7593 0.1015 0.051 Uiso 1 1 calc R
C11 C 1.01713(12) 0.78889(11) -0.07669(7) 0.0244(3) Uani 1 1 d .
C12 C 0.99849(15) 0.91705(12) -0.08782(8) 0.0328(3) Uani 1 1 d .
H12 H 0.9705 0.9686 -0.0478 0.039 Uiso 1 1 calc R
C13 C 1.02038(18) 0.97087(14) -0.15710(9) 0.0458(4) Uani 1 1 d .
H13 H 1.0086 1.0589 -0.1637 0.055 Uiso 1 1 calc R
C14 C 1.05883(19) 0.89769(15) -0.21570(9) 0.0488(4) Uani 1 1 d .
H14 H 1.0713 0.9343 -0.2632 0.059 Uiso 1 1 calc R
C15 C 1.07934(19) 0.76982(15) -0.20520(9) 0.0482(4) Uani 1 1 d .
H15 H 1.1076 0.7189 -0.2454 0.058 Uiso 1 1 calc R
C16 C 1.05870(15) 0.71609(13) -0.13621(8) 0.0353(3) Uani 1 1 d .
H16 H 1.0732 0.6284 -0.1296 0.042 Uiso 1 1 calc R
C17 C 0.87293(14) 0.22827(13) 0.20536(7) 0.0322(3) Uani 1 1 d .
C18 C 0.8029(2) 0.31061(18) 0.26142(9) 0.0600(5) Uani 1 1 d .
H18A H 0.8555 0.3865 0.2706 0.090 Uiso 1 1 calc R
H18B H 0.7918 0.2639 0.3078 0.090 Uiso 1 1 calc R
H18C H 0.7160 0.3347 0.2421 0.090 Uiso 1 1 calc R
C19 C 1.01066(17) 0.19374(17) 0.23177(8) 0.0458(4) Uani 1 1 d .
H19A H 1.0549 0.1430 0.1939 0.069 Uiso 1 1 calc R
H19B H 1.0043 0.1452 0.2778 0.069 Uiso 1 1 calc R
H19C H 1.0616 0.2708 0.2407 0.069 Uiso 1 1 calc R
C20 C 0.79086(17) 0.11368(15) 0.18592(9) 0.0457(4) Uani 1 1 d .
H20A H 0.7086 0.1407 0.1621 0.069 Uiso 1 1 calc R
H20B H 0.7702 0.0667 0.2311 0.069 Uiso 1 1 calc R
H20C H 0.8407 0.0596 0.1520 0.069 Uiso 1 1 calc R
O1 O 0.98434(10) 0.17182(8) 0.06698(5) 0.0337(2) Uani 1 1 d .
O2 O 0.88365(10) 0.31375(8) 0.14056(5) 0.0302(2) 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 0.0016 '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
N2 N1 C1 111.10(10)
N1 N2 C2 111.53(11)
C6 N3 C5 109.50(9)
C6 N3 C9 116.93(9)
C5 N3 C9 111.99(9)
N1 C1 C7 105.35(9)
N1 C1 C6 110.24(9)
C7 C1 C6 112.57(9)
N1 C1 C3 102.48(9)
C7 C1 C3 108.38(9)
C6 C1 C3 116.78(9)
N2 C2 C3 104.04(10)
N2 C2 H2A 110.9
C3 C2 H2A 110.9
N2 C2 H2B 110.9
C3 C2 H2B 110.9
H2A C2 H2B 109.0
C2 C3 C4 109.70(10)
C2 C3 C1 99.36(10)
C4 C3 C1 112.33(9)
C2 C3 H3 111.6
C4 C3 H3 111.6
C1 C3 H3 111.6
C5 C4 C3 112.85(10)
C5 C4 H4A 109.0
C3 C4 H4A 109.0
C5 C4 H4B 109.0
C3 C4 H4B 109.0
H4A C4 H4B 107.8
N3 C5 C4 108.90(9)
N3 C5 H5A 109.9
C4 C5 H5A 109.9
N3 C5 H5B 109.9
C4 C5 H5B 109.9
H5A C5 H5B 108.3
N3 C6 C8 112.92(9)
N3 C6 C1 106.99(9)
C8 C6 C1 109.95(9)
N3 C6 H6 109.0
C8 C6 H6 109.0
C1 C6 H6 109.0
O1 C7 O2 125.86(11)
O1 C7 C1 122.93(11)
O2 C7 C1 111.18(10)
C6 C8 H8A 109.5
C6 C8 H8B 109.5
H8A C8 H8B 109.5
C6 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
N3 C9 C11 108.48(9)
N3 C9 C10 114.23(10)
C11 C9 C10 114.38(10)
N3 C9 H9 106.4
C11 C9 H9 106.4
C10 C9 H9 106.4
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
C12 C11 C16 118.31(12)
C12 C11 C9 122.35(11)
C16 C11 C9 119.22(11)
C11 C12 C13 120.69(14)
C11 C12 H12 119.7
C13 C12 H12 119.7
C14 C13 C12 120.43(14)
C14 C13 H13 119.8
C12 C13 H13 119.8
C13 C14 C15 119.50(14)
C13 C14 H14 120.2
C15 C14 H14 120.2
C16 C15 C14 120.22(15)
C16 C15 H15 119.9
C14 C15 H15 119.9
C15 C16 C11 120.82(13)
C15 C16 H16 119.6
C11 C16 H16 119.6
O2 C17 C18 102.04(11)
O2 C17 C20 110.37(11)
C18 C17 C20 111.21(14)
O2 C17 C19 109.14(11)
C18 C17 C19 111.07(14)
C20 C17 C19 112.51(13)
C17 C18 H18A 109.5
C17 C18 H18B 109.5
H18A C18 H18B 109.5
C17 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C17 C19 H19A 109.5
C17 C19 H19B 109.5
H19A C19 H19B 109.5
C17 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C17 C20 H20A 109.5
C17 C20 H20B 109.5
H20A C20 H20B 109.5
C17 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
C7 O2 C17 120.79(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 N2 1.2432(15)
N1 C1 1.5152(15)
N2 C2 1.4910(19)
N3 C6 1.4670(14)
N3 C5 1.4676(14)
N3 C9 1.4744(14)
C1 C7 1.5399(16)
C1 C6 1.5418(16)
C1 C3 1.5421(16)
C2 C3 1.5220(18)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.5330(17)
C3 H3 1.0000
C4 C5 1.5087(18)
C4 H4A 0.9900
C4 H4B 0.9900
C5 H5A 0.9900
C5 H5B 0.9900
C6 C8 1.5262(16)
C6 H6 1.0000
C7 O1 1.2042(15)
C7 O2 1.3255(15)
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 C11 1.5264(16)
C9 C10 1.5315(18)
C9 H9 1.0000
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 C12 1.3884(17)
C11 C16 1.3895(18)
C12 C13 1.394(2)
C12 H12 0.9500
C13 C14 1.370(2)
C13 H13 0.9500
C14 C15 1.386(2)
C14 H14 0.9500
C15 C16 1.386(2)
C15 H15 0.9500
C16 H16 0.9500
C17 O2 1.4852(15)
C17 C18 1.514(2)
C17 C20 1.515(2)
C17 C19 1.519(2)
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 0.9800
