#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/11/7151129.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_7151129
loop_
_publ_author_name
'Hosseini, Masood'
'Grau, Jakob S.'
'Sørensen, Kasper K'
'Søtofte, Inger'
'Tanner, David'
'Murray, Anthony'
'Tønder, Janne E'
_publ_section_title
;
 Short and efficient diastereoselective synthesis of
 pyrrolidinone-containing dipeptide analogues.
;
_journal_issue                   14
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2207
_journal_page_last               2210
_journal_paper_doi               10.1039/b705093c
_journal_volume                  5
_journal_year                    2007
_chemical_formula_moiety         C12H21N3O2,1.5H2O
_chemical_formula_sum            'C12 H24 N3 O3.5'
_chemical_formula_weight         266.34
_chemical_name_systematic
;
?
;
_space_group_IT_number           77
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4c'
_symmetry_space_group_name_H-M   'P 42'
_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                   12.9386(8)
_cell_length_b                   12.9386(8)
_cell_length_c                   8.5628(7)
_cell_measurement_reflns_used    20006
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.04
_cell_measurement_theta_min      1.57
_cell_volume                     1433.48(17)
_computing_cell_refinement       'SAINT (Bruker AXS,1998)'
_computing_data_collection       'SMART (Bruker AXS,1998)'
_computing_data_reduction        'SAINT (Bruker AXS,1998)'
_computing_molecular_graphics    'SHELXTL,ver.6.12 (Sheldrick,2001)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXTL,ver.6.12 (Sheldrick,2001)'
_computing_structure_solution    'SHELXTL,ver.6.12 (Sheldrick,2001)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART 1K CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0753
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            20006
_diffrn_reflns_theta_full        28.04
_diffrn_reflns_theta_max         28.04
_diffrn_reflns_theta_min         1.57
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8487
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.230
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         1858
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.228
_refine_ls_R_factor_all          0.1077
_refine_ls_R_factor_gt           0.1025
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0487P)²+2.5178P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2067
_refine_ls_wR_factor_ref         0.2087
_reflns_number_gt                1779
_reflns_number_total             1858
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b705093c.txt
_cod_data_source_block           mah4
_cod_original_formula_sum        'C12 H24 N3 O3.50'
_cod_database_code               7151129
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-y, x, z+1/2'
'y, -x, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2412(2) 0.3060(3) 0.2742(4) 0.0262(8) Uani 1 1 d . . .
C1 C 0.3212(4) 0.2661(4) 0.3196(7) 0.0307(13) Uani 1 1 d . . .
N1 N 0.3360(6) 0.2426(6) 0.4674(7) 0.085(3) Uani 1 1 d . . .
H11 H 0.2875 0.2556 0.5367 0.102 Uiso 1 1 calc R . .
H12 H 0.3945 0.2138 0.4970 0.102 Uiso 1 1 calc R . .
C2 C 0.4102(4) 0.2464(5) 0.2107(10) 0.053(2) Uani 1 1 d . . .
H2 H 0.4598 0.1970 0.2603 0.063 Uiso 1 1 calc R . .
C3 C 0.4662(7) 0.3476(8) 0.1717(18) 0.102(5) Uani 1 1 d . . .
H31 H 0.4375 0.4054 0.2337 0.122 Uiso 1 1 calc R . .
H32 H 0.5410 0.3415 0.1944 0.122 Uiso 1 1 calc R . .
C4 C 0.4488(7) 0.3648(6) 0.003(2) 0.102(5) Uani 1 1 d . . .
H41 H 0.5091 0.3991 -0.0460 0.122 Uiso 1 1 calc R . .
H42 H 0.3865 0.4077 -0.0151 0.122 Uiso 1 1 calc R . .
C5 C 0.4339(7) 0.2555(4) -0.0624(11) 0.066(3) Uani 1 1 d . . .
H51 H 0.3952 0.2568 -0.1621 0.079 Uiso 1 1 calc R . .
H52 H 0.5011 0.2207 -0.0791 0.079 Uiso 1 1 calc R . .
N2 N 0.3738(4) 0.2039(3) 0.0617(7) 0.0402(13) Uani 1 1 d . . .
C6 C 0.3839(4) 0.0916(4) 0.0545(7) 0.0336(13) Uani 1 1 d . . .
H6 H 0.4596 0.0761 0.0528 0.040 Uiso 1 1 calc R . .
C7 C 0.3376(6) 0.0428(4) -0.0926(7) 0.0422(17) Uani 1 1 d . . .
H7 H 0.3912 0.0423 -0.1767 0.051 Uiso 1 1 calc R . .
C8 C 0.2370(7) 0.0896(5) -0.1587(10) 0.065(3) Uani 1 1 d . . .
H8 H 0.2532 0.1623 -0.1902 0.078 Uiso 1 1 calc R . .
C9 C 0.1495(7) 0.0949(7) -0.0440(13) 0.079(3) Uani 1 1 d . . .
H91 H 0.0863 0.1164 -0.0981 0.119 Uiso 1 1 calc R . .
H92 H 0.1661 0.1452 0.0379 0.119 Uiso 1 1 calc R . .
H93 H 0.1389 0.0267 0.0031 0.119 Uiso 1 1 calc R . .
C10 C 0.2060(11) 0.0323(7) -0.3056(12) 0.121(6) Uani 1 1 d . . .
H101 H 0.2635 0.0333 -0.3801 0.182 Uiso 1 1 calc R . .
H102 H 0.1456 0.0659 -0.3524 0.182 Uiso 1 1 calc R . .
H103 H 0.1889 -0.0394 -0.2794 0.182 Uiso 1 1 calc R . .
N3 N 0.3218(4) -0.0631(3) -0.0373(5) 0.0342(11) Uani 1 1 d . . .
H3 H 0.3124 -0.1151 -0.1021 0.041 Uiso 1 1 calc R . .
C11 C 0.3223(5) -0.0759(5) 0.1170(6) 0.0345(14) Uani 1 1 d . . .
O2 O 0.3104(4) -0.1571(4) 0.1866(5) 0.0549(15) Uani 1 1 d . . .
C12 C 0.3382(5) 0.0306(5) 0.1889(7) 0.0378(15) Uani 1 1 d . . .
H121 H 0.2718 0.0608 0.2238 0.045 Uiso 1 1 calc R . .
H122 H 0.3864 0.0276 0.2785 0.045 Uiso 1 1 calc R . .
O3 O 0.1678(4) 0.3976(7) -0.0066(6) 0.078(2) Uani 1 1 d D . .
H3A H 0.201(7) 0.354(7) 0.057(11) 0.118 Uiso 1 1 d D . .
H3B H 0.156(9) 0.367(8) -0.098(7) 0.118 Uiso 1 1 d D . .
O4 O 0.0517(5) 0.5394(5) 0.0735(9) 0.0281(16) Uani 0.50 1 d PD . .
H4A H 0.075(9) 0.474(4) 0.054(18) 0.042 Uiso 0.50 1 d PD . .
H4B H 0.0000 0.5000 0.110(7) 0.042 Uiso 0.50 2 d SPD . .
H4C H 0.0000 0.5000 0.035(7) 0.042 Uiso 0.50 2 d SPD . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 121.9(6) . . ?
O1 C1 C2 121.6(6) . . ?
N1 C1 C2 116.5(6) . . ?
C1 N1 H11 120.0 . . ?
C1 N1 H12 120.0 . . ?
H11 N1 H12 120.0 . . ?
N2 C2 C1 110.9(5) . . ?
N2 C2 C3 106.4(8) . . ?
C1 C2 C3 110.7(5) . . ?
N2 C2 H2 109.6 . . ?
C1 C2 H2 109.6 . . ?
C3 C2 H2 109.6 . . ?
C4 C3 C2 105.6(9) . . ?
C4 C3 H31 110.6 . . ?
C2 C3 H31 110.6 . . ?
C4 C3 H32 110.6 . . ?
C2 C3 H32 110.6 . . ?
H31 C3 H32 108.7 . . ?
C3 C4 C5 103.6(10) . . ?
C3 C4 H41 111.0 . . ?
C5 C4 H41 111.0 . . ?
C3 C4 H42 111.0 . . ?
C5 C4 H42 111.0 . . ?
H41 C4 H42 109.0 . . ?
N2 C5 C4 102.8(8) . . ?
N2 C5 H51 111.2 . . ?
C4 C5 H51 111.2 . . ?
N2 C5 H52 111.2 . . ?
C4 C5 H52 111.2 . . ?
H51 C5 H52 109.1 . . ?
C6 N2 C2 112.4(6) . . ?
C6 N2 C5 111.8(4) . . ?
C2 N2 C5 106.7(5) . . ?
N2 C6 C12 116.8(5) . . ?
N2 C6 C7 114.2(5) . . ?
C12 C6 C7 104.9(4) . . ?
N2 C6 H6 106.8 . . ?
C12 C6 H6 106.8 . . ?
C7 C6 H6 106.8 . . ?
N3 C7 C6 100.1(5) . . ?
N3 C7 C8 111.6(6) . . ?
C6 C7 C8 118.0(5) . . ?
N3 C7 H7 108.9 . . ?
C6 C7 H7 108.9 . . ?
C8 C7 H7 108.9 . . ?
C9 C8 C10 111.5(9) . . ?
C9 C8 C7 114.5(7) . . ?
C10 C8 C7 109.6(6) . . ?
C9 C8 H8 107.0 . . ?
C10 C8 H8 107.0 . . ?
C7 C8 H8 107.0 . . ?
C8 C9 H91 109.5 . . ?
C8 C9 H92 109.5 . . ?
H91 C9 H92 109.5 . . ?
C8 C9 H93 109.5 . . ?
H91 C9 H93 109.5 . . ?
H92 C9 H93 109.5 . . ?
C8 C10 H101 109.5 . . ?
C8 C10 H102 109.5 . . ?
H101 C10 H102 109.5 . . ?
C8 C10 H103 109.5 . . ?
H101 C10 H103 109.5 . . ?
H102 C10 H103 109.5 . . ?
C11 N3 C7 115.9(5) . . ?
C11 N3 H3 122.1 . . ?
C7 N3 H3 122.1 . . ?
O2 C11 N3 126.3(5) . . ?
O2 C11 C12 126.9(5) . . ?
N3 C11 C12 106.8(6) . . ?
C6 C12 C11 102.6(4) . . ?
C6 C12 H121 111.3 . . ?
C11 C12 H121 111.3 . . ?
C6 C12 H122 111.3 . . ?
C11 C12 H122 111.3 . . ?
H121 C12 H122 109.2 . . ?
H3A O3 H3B 109(10) . . ?
O4 O4 H4A 73(8) 2_565 . ?
O4 O4 H4B 21(4) 2_565 . ?
H4A O4 H4B 78(8) . . ?
O4 O4 H4C 21(4) 2_565 . ?
H4A O4 H4C 70(8) . . ?
H4B O4 H4C 42(5) . . ?
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
O1 C1 1.220(6) . ?
C1 N1 1.315(9) . ?
C1 C2 1.504(9) . ?
N1 H11 0.8800 . ?
N1 H12 0.8800 . ?
C2 N2 1.467(9) . ?
C2 C3 1.533(12) . ?
C2 H2 1.0000 . ?
C3 C4 1.482(19) . ?
C3 H31 0.9900 . ?
C3 H32 0.9900 . ?
C4 C5 1.533(11) . ?
C4 H41 0.9900 . ?
C4 H42 0.9900 . ?
C5 N2 1.476(9) . ?
C5 H51 0.9900 . ?
C5 H52 0.9900 . ?
N2 C6 1.460(6) . ?
C6 C12 1.516(8) . ?
C6 C7 1.531(9) . ?
C6 H6 1.0000 . ?
C7 N3 1.464(7) . ?
C7 C8 1.543(11) . ?
C7 H7 1.0000 . ?
C8 C9 1.501(14) . ?
C8 C10 1.515(11) . ?
C8 H8 1.0000 . ?
C9 H91 0.9800 . ?
C9 H92 0.9800 . ?
C9 H93 0.9800 . ?
C10 H101 0.9800 . ?
C10 H102 0.9800 . ?
C10 H103 0.9800 . ?
N3 C11 1.332(7) . ?
N3 H3 0.8800 . ?
C11 O2 1.217(8) . ?
C11 C12 1.524(8) . ?
C12 H121 0.9900 . ?
C12 H122 0.9900 . ?
O3 H3A 0.90(2) . ?
O3 H3B 0.90(2) . ?
O4 O4 1.683(14) 2_565 ?
O4 H4A 0.91(2) . ?
O4 H4B 0.90(2) . ?
O4 H4C 0.90(2) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 N2 -43.4(8) . . . . ?
N1 C1 C2 N2 139.7(7) . . . . ?
O1 C1 C2 C3 74.4(9) . . . . ?
N1 C1 C2 C3 -102.4(10) . . . . ?
N2 C2 C3 C4 6.4(9) . . . . ?
C1 C2 C3 C4 -114.1(8) . . . . ?
C2 C3 C4 C5 -27.3(10) . . . . ?
C3 C4 C5 N2 38.4(9) . . . . ?
C1 C2 N2 C6 -98.5(6) . . . . ?
C3 C2 N2 C6 141.1(6) . . . . ?
C1 C2 N2 C5 138.6(6) . . . . ?
C3 C2 N2 C5 18.2(6) . . . . ?
C4 C5 N2 C6 -158.1(7) . . . . ?
C4 C5 N2 C2 -34.9(8) . . . . ?
C2 N2 C6 C12 51.7(7) . . . . ?
C5 N2 C6 C12 171.7(6) . . . . ?
C2 N2 C6 C7 174.6(5) . . . . ?
C5 N2 C6 C7 -65.4(7) . . . . ?
N2 C6 C7 N3 -158.1(5) . . . . ?
C12 C6 C7 N3 -29.0(6) . . . . ?
N2 C6 C7 C8 -36.9(8) . . . . ?
C12 C6 C7 C8 92.3(7) . . . . ?
N3 C7 C8 C9 59.7(7) . . . . ?
C6 C7 C8 C9 -55.4(8) . . . . ?
N3 C7 C8 C10 -66.4(9) . . . . ?
C6 C7 C8 C10 178.5(8) . . . . ?
C6 C7 N3 C11 17.8(7) . . . . ?
C8 C7 N3 C11 -107.9(7) . . . . ?
C7 N3 C11 O2 179.8(6) . . . . ?
C7 N3 C11 C12 1.1(8) . . . . ?
N2 C6 C12 C11 158.0(5) . . . . ?
C7 C6 C12 C11 30.4(6) . . . . ?
O2 C11 C12 C6 161.4(7) . . . . ?
N3 C11 C12 C6 -19.9(7) . . . . ?
