#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:12:37 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178425 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/46/4024688.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_4024688
loop_
_publ_author_name
'Meryem Benohoud'
'Loïc Leman'
'Silvia H. Cardoso'
'Pascal Retailleau'
'Philippe Dauban'
'Josiane Thierry'
'Robert H. Dodd'
_publ_contact_author_address
;Institut de Chimie des Substances Naturelles, UPR 2301,
Centre National de la Recherche Scientifique,
 bât. 27, 1 av. de la Terrasse, F-91198 Gif-sur-Yvette, France

;
_publ_contact_author_email       dodd@icsn.cnrs-gif.fr
_publ_contact_author_fax         '33 1 69077247'
_publ_contact_author_name        'DODD, Robert H.'
_publ_contact_author_phone       '33 1 69824594'
_publ_section_title
;
Total Synthesis and Absolute Configuration of the Natural Amino Acid
Tetrahydrolathyrine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5331
_journal_page_last               5336
_journal_paper_doi               10.1021/jo900800x
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C16 H20 N4 O4'
_chemical_formula_sum            'C16 H20 N4 O4'
_chemical_formula_weight         332.36
_chemical_name_systematic
; 
 benzyl (S)-6-(((S)-2-oxooxazolidin-4-yl)methyl)-1,4,5,6-
 tetrahydropyrimidin-2-ylcarbamate 
;
_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_date             18-02-09
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.828(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.886(2)
_cell_length_b                   12.116(5)
_cell_length_c                   23.233(5)
_cell_measurement_reflns_used    1315
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.782
_cell_measurement_theta_min      0.998
_cell_volume                     1651.0(10)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_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     0.71069
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0786
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4204
_diffrn_reflns_theta_full        19.76
_diffrn_reflns_theta_max         19.76
_diffrn_reflns_theta_min         2.43
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'flat parallelepiped'
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         1515
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_gt           0.0524
_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)+(0.0705P)²+0.2030P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1406
_reflns_number_gt                1011
_reflns_number_total             1515
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900800x_si_002.cif
_cod_data_source_block           mb210-b
_cod_original_sg_symbol_H-M      P21
_cod_database_code               4024688
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
O1A O 0.3739(13) 0.4712(7) 0.2384(3) 0.065(2) Uani 1 1 d . . .
O2A O 0.6226(13) 0.5120(8) 0.3148(4) 0.074(3) Uani 1 1 d . . .
N1A N 0.5801(15) 0.3338(11) 0.2773(4) 0.059(3) Uani 1 1 d . . .
H1A H 0.5060 0.2951 0.2510 0.071 Uiso 1 1 calc R . .
N2A N 0.7422(17) 0.1759(11) 0.3111(4) 0.084(4) Uani 1 1 d . . .
N3A N 0.8622(15) 0.3378(9) 0.3543(4) 0.076(3) Uani 1 1 d . . .
H31 H 0.8479 0.4084 0.3558 0.091 Uiso 1 1 calc R . .
C14A C 1.228(2) 0.4668(12) 0.4274(5) 0.076(4) Uani 1 1 d . . .
H14A H 1.1072 0.5077 0.4049 0.091 Uiso 1 1 calc R . .
C15A C 1.195(2) 0.4705(15) 0.4914(6) 0.110(6) Uani 1 1 d . . .
H15A H 1.0429 0.4957 0.4977 0.132 Uiso 1 1 calc R . .
H15B H 1.2182 0.3980 0.5086 0.132 Uiso 1 1 calc R . .
O3A O 1.3655(18) 0.5478(11) 0.5162(4) 0.119(4) Uani 1 1 d . . .
N4A N 1.4422(18) 0.5244(11) 0.4290(5) 0.089(3) Uani 1 1 d . . .
H41 H 1.5211 0.5250 0.3995 0.107 Uiso 1 1 calc R . .
C16A C 1.514(3) 0.5765(16) 0.4774(6) 0.089(5) Uani 1 1 d . . .
O4A O 1.6757(17) 0.6323(10) 0.4877(4) 0.120(4) Uani 1 1 d . . .
C1A C 0.309(2) 0.5863(12) 0.2384(6) 0.087(4) Uani 1 1 d . . .
H1A1 H 0.4397 0.6329 0.2338 0.105 Uiso 1 1 calc R . .
H1A2 H 0.2466 0.6052 0.2745 0.105 Uiso 1 1 calc R . .
C2A C 0.1324(19) 0.6020(11) 0.1890(6) 0.059(3) Uani 1 1 d . . .
C3A C 0.158(2) 0.6745(11) 0.1446(7) 0.074(4) Uani 1 1 d . . .
H3A H 0.2908 0.7163 0.1444 0.088 Uiso 1 1 calc R . .
C4A C -0.013(3) 0.6854(13) 0.1001(6) 0.087(5) Uani 1 1 d . . .
H4A H 0.0075 0.7336 0.0698 0.104 Uiso 1 1 calc R . .
C5A C -0.211(2) 0.6269(15) 0.0999(6) 0.091(5) Uani 1 1 d . . .
H5A H -0.3271 0.6367 0.0706 0.109 Uiso 1 1 calc R . .
C6A C -0.236(2) 0.5536(14) 0.1438(7) 0.087(4) Uani 1 1 d . . .
H6A H -0.3678 0.5111 0.1436 0.104 Uiso 1 1 calc R . .
C7A C -0.069(2) 0.5425(12) 0.1879(5) 0.073(4) Uani 1 1 d . . .
H7A H -0.0910 0.4939 0.2179 0.088 Uiso 1 1 calc R . .
C8A C 0.539(2) 0.4421(16) 0.2802(6) 0.062(4) Uani 1 1 d . . .
C9A C 0.7320(19) 0.2846(15) 0.3140(5) 0.060(4) Uani 1 1 d . . .
C10A C 0.886(3) 0.1072(15) 0.3535(6) 0.122(6) Uani 1 1 d . . .
H10A H 0.7983 0.0867 0.3854 0.146 Uiso 1 1 calc R . .
H10B H 0.9327 0.0402 0.3350 0.146 Uiso 1 1 calc R . .
C11A C 1.083(2) 0.1700(14) 0.3745(7) 0.108(5) Uani 1 1 d . . .
H11A H 1.1827 0.1774 0.3436 0.129 Uiso 1 1 calc R . .
H11B H 1.1652 0.1289 0.4055 0.129 Uiso 1 1 calc R . .
C12A C 1.031(2) 0.2852(13) 0.3969(6) 0.080(4) Uani 1 1 d . . .
H12A H 0.9653 0.2787 0.4342 0.097 Uiso 1 1 calc R . .
C13A C 1.249(2) 0.3506(13) 0.4047(5) 0.087(4) Uani 1 1 d . . .
H13A H 1.3137 0.3544 0.3677 0.104 Uiso 1 1 calc R . .
H13B H 1.3559 0.3105 0.4310 0.104 Uiso 1 1 calc R . .
O1B O 0.7540(14) -0.0614(8) 0.2494(4) 0.084(3) Uani 1 1 d U . .
O2B O 0.5355(13) -0.1050(8) 0.1693(4) 0.079(3) Uani 1 1 d . . .
O3B O -0.4171(16) -0.1229(9) -0.0456(4) 0.099(3) Uani 1 1 d . . .
O4B O -0.6319(16) -0.2120(9) 0.0132(4) 0.095(3) Uani 1 1 d . . .
N1B N 0.5035(17) 0.0606(10) 0.2151(3) 0.062(3) Uani 1 1 d . . .
H1B H 0.5689 0.1020 0.2417 0.075 Uiso 1 1 calc R . .
N2B N 0.2640(16) 0.2039(9) 0.1929(4) 0.071(3) Uani 1 1 d U . .
N3B N 0.2005(15) 0.0376(9) 0.1449(4) 0.067(3) Uani 1 1 d . . .
H32 H 0.2464 -0.0288 0.1397 0.080 Uiso 1 1 calc R . .
N4B N -0.3893(17) -0.0742(10) 0.0442(4) 0.082(4) Uani 1 1 d . . .
H42 H -0.4053 -0.0778 0.0806 0.098 Uiso 1 1 calc R . .
C1B C 0.854(2) -0.1669(13) 0.2484(6) 0.111(5) Uani 1 1 d U . .
H1B1 H 0.9447 -0.1737 0.2156 0.133 Uiso 1 1 calc R . .
H1B2 H 0.7372 -0.2236 0.2455 0.133 Uiso 1 1 calc R . .
C2B C 0.999(2) -0.1781(11) 0.3029(5) 0.072(3) Uani 1 1 d U . .
C3B C 1.206(2) -0.1299(14) 0.3122(6) 0.093(4) Uani 1 1 d U . .
H3B H 1.2647 -0.0919 0.2820 0.112 Uiso 1 1 calc R . .
C4B C 1.334(2) -0.1348(16) 0.3644(8) 0.117(6) Uani 1 1 d U . .
H4B H 1.4754 -0.1008 0.3694 0.141 Uiso 1 1 calc R . .
C5B C 1.249(4) -0.1900(17) 0.4083(8) 0.132(7) Uani 1 1 d U . .
H5B H 1.3315 -0.1920 0.4442 0.159 Uiso 1 1 calc R . .
C6B C 1.046(3) -0.2423(16) 0.4007(8) 0.119(6) Uani 1 1 d U . .
H6B H 0.9883 -0.2807 0.4309 0.143 Uiso 1 1 calc R . .
C7B C 0.924(2) -0.2377(12) 0.3470(7) 0.089(4) Uani 1 1 d U . .
H7B H 0.7883 -0.2766 0.3410 0.107 Uiso 1 1 calc R . .
C8B C 0.591(2) -0.0416(14) 0.2076(6) 0.066(4) Uani 1 1 d . . .
C9B C 0.3214(19) 0.1006(12) 0.1836(5) 0.059(3) Uani 1 1 d U . .
C10B C 0.059(2) 0.2522(12) 0.1626(5) 0.087(4) Uani 1 1 d . . .
H10C H 0.0823 0.3307 0.1572 0.104 Uiso 1 1 calc R . .
H10D H -0.0694 0.2426 0.1855 0.104 Uiso 1 1 calc R . .
C11B C 0.010(2) 0.1973(13) 0.1047(5) 0.084(4) Uani 1 1 d . . .
H11C H -0.1324 0.2254 0.0864 0.101 Uiso 1 1 calc R . .
H11D H 0.1302 0.2151 0.0801 0.101 Uiso 1 1 calc R . .
C12B C -0.0058(19) 0.0754(13) 0.1108(5) 0.069(4) Uani 1 1 d . . .
H12B H -0.1410 0.0561 0.1306 0.083 Uiso 1 1 calc R . .
C13B C -0.0107(17) 0.0141(11) 0.0527(4) 0.068(3) Uani 1 1 d . . .
H13C H 0.0936 0.0505 0.0286 0.081 Uiso 1 1 calc R . .
H13D H 0.0446 -0.0605 0.0597 0.081 Uiso 1 1 calc R . .
C14B C -0.2426(18) 0.0083(12) 0.0198(6) 0.076(4) Uani 1 1 d . . .
H14B H -0.3160 0.0809 0.0176 0.091 Uiso 1 1 calc R . .
C15B C -0.238(2) -0.0427(13) -0.0401(5) 0.094(5) Uani 1 1 d . . .
H15C H -0.2623 0.0135 -0.0697 0.112 Uiso 1 1 calc R . .
H15D H -0.0916 -0.0777 -0.0441 0.112 Uiso 1 1 calc R . .
C16B C -0.493(2) -0.1412(15) 0.0074(6) 0.075(4) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8A O1A C1A 115.1(12) . . ?
C9A N1A C8A 121.6(12) . . ?
C9A N1A H1A 119.2 . . ?
C8A N1A H1A 119.2 . . ?
C9A N2A C10A 123.2(12) . . ?
C9A N3A C12A 125.2(12) . . ?
C9A N3A H31 117.4 . . ?
C12A N3A H31 117.4 . . ?
N4A C14A C13A 111.3(11) . . ?
N4A C14A C15A 98.2(10) . . ?
C13A C14A C15A 113.0(13) . . ?
N4A C14A H14A 111.2 . . ?
C13A C14A H14A 111.2 . . ?
C15A C14A H14A 111.2 . . ?
O3A C15A C14A 105.6(11) . . ?
O3A C15A H15A 110.6 . . ?
C14A C15A H15A 110.6 . . ?
O3A C15A H15B 110.6 . . ?
C14A C15A H15B 110.6 . . ?
H15A C15A H15B 108.8 . . ?
C16A O3A C15A 111.3(11) . . ?
C16A N4A C14A 118.0(12) . . ?
C16A N4A H41 121.0 . . ?
C14A N4A H41 121.0 . . ?
O4A C16A N4A 129.9(15) . . ?
O4A C16A O3A 124.7(15) . . ?
N4A C16A O3A 105.3(14) . . ?
O1A C1A C2A 106.8(10) . . ?
O1A C1A H1A1 110.4 . . ?
C2A C1A H1A1 110.4 . . ?
O1A C1A H1A2 110.4 . . ?
C2A C1A H1A2 110.4 . . ?
H1A1 C1A H1A2 108.6 . . ?
C3A C2A C7A 117.9(12) . . ?
C3A C2A C1A 123.0(13) . . ?
C7A C2A C1A 119.0(14) . . ?
C2A C3A C4A 120.0(12) . . ?
C2A C3A H3A 120.0 . . ?
C4A C3A H3A 120.0 . . ?
C5A C4A C3A 121.3(13) . . ?
C5A C4A H4A 119.4 . . ?
C3A C4A H4A 119.4 . . ?
C4A C5A C6A 118.7(13) . . ?
C4A C5A H5A 120.6 . . ?
C6A C5A H5A 120.6 . . ?
C7A C6A C5A 120.4(13) . . ?
C7A C6A H6A 119.8 . . ?
C5A C6A H6A 119.8 . . ?
C6A C7A C2A 121.6(13) . . ?
C6A C7A H7A 119.2 . . ?
C2A C7A H7A 119.2 . . ?
O2A C8A N1A 129.8(13) . . ?
O2A C8A O1A 120.3(16) . . ?
N1A C8A O1A 109.8(14) . . ?
N2A C9A N1A 116.6(13) . . ?
N2A C9A N3A 119.7(13) . . ?
N1A C9A N3A 123.7(15) . . ?
C11A C10A N2A 108.9(15) . . ?
C11A C10A H10A 109.9 . . ?
N2A C10A H10A 109.9 . . ?
C11A C10A H10B 109.9 . . ?
N2A C10A H10B 109.9 . . ?
H10A C10A H10B 108.3 . . ?
C10A C11A C12A 114.8(13) . . ?
C10A C11A H11A 108.6 . . ?
C12A C11A H11A 108.6 . . ?
C10A C11A H11B 108.6 . . ?
C12A C11A H11B 108.6 . . ?
H11A C11A H11B 107.6 . . ?
N3A C12A C13A 111.7(12) . . ?
N3A C12A C11A 107.9(11) . . ?
C13A C12A C11A 109.1(11) . . ?
N3A C12A H12A 109.4 . . ?
C13A C12A H12A 109.4 . . ?
C11A C12A H12A 109.4 . . ?
C12A C13A C14A 115.9(11) . . ?
C12A C13A H13A 108.3 . . ?
C14A C13A H13A 108.3 . . ?
C12A C13A H13B 108.3 . . ?
C14A C13A H13B 108.3 . . ?
H13A C13A H13B 107.4 . . ?
C8B O1B C1B 115.3(11) . . ?
C16B O3B C15B 109.1(11) . . ?
C9B N1B C8B 123.7(12) . . ?
C9B N1B H1B 118.2 . . ?
C8B N1B H1B 118.2 . . ?
C9B N2B C10B 120.8(11) . . ?
C9B N3B C12B 123.7(11) . . ?
C9B N3B H32 118.2 . . ?
C12B N3B H32 118.2 . . ?
C16B N4B C14B 115.7(11) . . ?
C16B N4B H42 122.1 . . ?
C14B N4B H42 122.1 . . ?
O1B C1B C2B 106.4(11) . . ?
O1B C1B H1B1 110.5 . . ?
C2B C1B H1B1 110.5 . . ?
O1B C1B H1B2 110.5 . . ?
C2B C1B H1B2 110.5 . . ?
H1B1 C1B H1B2 108.6 . . ?
C3B C2B C7B 117.0(13) . . ?
C3B C2B C1B 123.1(14) . . ?
C7B C2B C1B 119.8(14) . . ?
C2B C3B C4B 122.7(14) . . ?
C2B C3B H3B 118.7 . . ?
C4B C3B H3B 118.7 . . ?
C5B C4B C3B 118.7(16) . . ?
C5B C4B H4B 120.6 . . ?
C3B C4B H4B 120.6 . . ?
C4B C5B C6B 120.8(17) . . ?
C4B C5B H5B 119.6 . . ?
C6B C5B H5B 119.6 . . ?
C5B C6B C7B 118.8(17) . . ?
C5B C6B H6B 120.6 . . ?
C7B C6B H6B 120.6 . . ?
C2B C7B C6B 121.8(14) . . ?
C2B C7B H7B 119.1 . . ?
C6B C7B H7B 119.1 . . ?
O2B C8B O1B 124.2(14) . . ?
O2B C8B N1B 126.7(13) . . ?
O1B C8B N1B 109.2(13) . . ?
N2B C9B N1B 117.3(12) . . ?
N2B C9B N3B 121.5(12) . . ?
N1B C9B N3B 121.2(13) . . ?
N2B C10B C11B 110.0(10) . . ?
N2B C10B H10C 109.7 . . ?
C11B C10B H10C 109.7 . . ?
N2B C10B H10D 109.7 . . ?
C11B C10B H10D 109.7 . . ?
H10C C10B H10D 108.2 . . ?
C12B C11B C10B 111.3(12) . . ?
C12B C11B H11C 109.4 . . ?
C10B C11B H11C 109.4 . . ?
C12B C11B H11D 109.4 . . ?
C10B C11B H11D 109.4 . . ?
H11C C11B H11D 108.0 . . ?
N3B C12B C11B 107.8(10) . . ?
N3B C12B C13B 106.1(10) . . ?
C11B C12B C13B 113.1(12) . . ?
N3B C12B H12B 109.9 . . ?
C11B C12B H12B 109.9 . . ?
C13B C12B H12B 109.9 . . ?
C14B C13B C12B 114.6(10) . . ?
C14B C13B H13C 108.6 . . ?
C12B C13B H13C 108.6 . . ?
C14B C13B H13D 108.6 . . ?
C12B C13B H13D 108.6 . . ?
H13C C13B H13D 107.6 . . ?
N4B C14B C13B 111.9(10) . . ?
N4B C14B C15B 97.7(10) . . ?
C13B C14B C15B 113.3(11) . . ?
N4B C14B H14B 111.1 . . ?
C13B C14B H14B 111.1 . . ?
C15B C14B H14B 111.1 . . ?
O3B C15B C14B 106.6(10) . . ?
O3B C15B H15C 110.4 . . ?
C14B C15B H15C 110.4 . . ?
O3B C15B H15D 110.4 . . ?
C14B C15B H15D 110.4 . . ?
H15C C15B H15D 108.6 . . ?
O4B C16B N4B 131.5(14) . . ?
O4B C16B O3B 119.8(15) . . ?
N4B C16B O3B 108.7(14) . . ?
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
O1A C8A 1.362(13) . ?
O1A C1A 1.446(15) . ?
O2A C8A 1.241(16) . ?
N1A C9A 1.325(14) . ?
N1A C8A 1.337(16) . ?
N1A H1A 0.8600 . ?
N2A C9A 1.320(16) . ?
N2A C10A 1.495(16) . ?
N3A C9A 1.325(14) . ?
N3A C12A 1.486(15) . ?
N3A H31 0.8600 . ?
C14A N4A 1.440(15) . ?
C14A C13A 1.512(17) . ?
C14A C15A 1.517(16) . ?
C14A H14A 0.9800 . ?
C15A O3A 1.455(16) . ?
C15A H15A 0.9700 . ?
C15A H15B 0.9700 . ?
O3A C16A 1.355(15) . ?
N4A C16A 1.328(15) . ?
N4A H41 0.8600 . ?
C16A O4A 1.174(17) . ?
C1A C2A 1.494(15) . ?
C1A H1A1 0.9700 . ?
C1A H1A2 0.9700 . ?
C2A C3A 1.372(16) . ?
C2A C7A 1.386(15) . ?
C3A C4A 1.390(15) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.364(18) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.370(18) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.365(15) . ?
C6A H6A 0.9300 . ?
C7A H7A 0.9300 . ?
C10A C11A 1.439(18) . ?
C10A H10A 0.9700 . ?
C10A H10B 0.9700 . ?
C11A C12A 1.529(19) . ?
C11A H11A 0.9700 . ?
C11A H11B 0.9700 . ?
C12A C13A 1.505(17) . ?
C12A H12A 0.9800 . ?
C13A H13A 0.9700 . ?
C13A H13B 0.9700 . ?
O1B C8B 1.329(14) . ?
O1B C1B 1.408(16) . ?
O2B C8B 1.200(15) . ?
O3B C16B 1.363(14) . ?
O3B C15B 1.432(14) . ?
O4B C16B 1.200(16) . ?
N1B C9B 1.337(13) . ?
N1B C8B 1.358(16) . ?
N1B H1B 0.8600 . ?
N2B C9B 1.319(16) . ?
N2B C10B 1.465(14) . ?
N3B C9B 1.338(14) . ?
N3B C12B 1.467(13) . ?
N3B H32 0.8600 . ?
N4B C16B 1.293(16) . ?
N4B C14B 1.466(15) . ?
N4B H42 0.8600 . ?
C1B C2B 1.474(15) . ?
C1B H1B1 0.9700 . ?
C1B H1B2 0.9700 . ?
C2B C3B 1.353(17) . ?
C2B C7B 1.356(17) . ?
C3B C4B 1.373(17) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.35(2) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.35(2) . ?
C5B H5B 0.9300 . ?
C6B C7B 1.384(18) . ?
C6B H6B 0.9300 . ?
C7B H7B 0.9300 . ?
C10B C11B 1.507(15) . ?
C10B H10C 0.9700 . ?
C10B H10D 0.9700 . ?
C11B C12B 1.488(18) . ?
C11B H11C 0.9700 . ?
C11B H11D 0.9700 . ?
C12B C13B 1.539(15) . ?
C12B H12B 0.9800 . ?
C13B C14B 1.509(13) . ?
C13B H13C 0.9700 . ?
C13B H13D 0.9700 . ?
C14B C15B 1.525(16) . ?
C14B H14B 0.9800 . ?
C15B H15C 0.9700 . ?
C15B H15D 0.9700 . ?
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
N1A H1A N2B 0.86 2.18 3.027(13) 169.5 .
N1B H1B N2A 0.86 2.04 2.894(14) 170.4 .
N3A H31 O2A 0.86 2.01 2.659(14) 131.7 .
N3B H32 O2B 0.86 2.01 2.647(13) 130.5 .
N4A H41 O2A 0.86 2.11 2.943(13) 163.2 1_655
N4B H42 O2B 0.86 2.14 3.000(12) 173.3 1_455
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
N4A C14A C15A O3A 11.7(14) . . . . ?
C13A C14A C15A O3A 129.1(13) . . . . ?
C14A C15A O3A C16A -9.4(16) . . . . ?
C13A C14A N4A C16A -130.8(13) . . . . ?
C15A C14A N4A C16A -12.2(16) . . . . ?
C14A N4A C16A O4A -176.0(16) . . . . ?
C14A N4A C16A O3A 7.1(17) . . . . ?
C15A O3A C16A O4A -175.0(15) . . . . ?
C15A O3A C16A N4A 2.1(16) . . . . ?
C8A O1A C1A C2A 178.4(9) . . . . ?
O1A C1A C2A C3A -120.9(13) . . . . ?
O1A C1A C2A C7A 60.3(13) . . . . ?
C7A C2A C3A C4A -0.9(17) . . . . ?
C1A C2A C3A C4A -179.6(11) . . . . ?
C2A C3A C4A C5A 1(2) . . . . ?
C3A C4A C5A C6A -2(2) . . . . ?
C4A C5A C6A C7A 2(2) . . . . ?
C5A C6A C7A C2A -2(2) . . . . ?
C3A C2A C7A C6A 1.1(18) . . . . ?
C1A C2A C7A C6A 179.9(12) . . . . ?
C9A N1A C8A O2A -1.4(19) . . . . ?
C9A N1A C8A O1A -178.9(9) . . . . ?
C1A O1A C8A O2A 0.1(14) . . . . ?
C1A O1A C8A N1A 177.8(10) . . . . ?
C10A N2A C9A N1A -173.2(10) . . . . ?
C10A N2A C9A N3A 3.6(19) . . . . ?
C8A N1A C9A N2A 173.3(11) . . . . ?
C8A N1A C9A N3A -3.3(17) . . . . ?
C12A N3A C9A N2A 2.2(17) . . . . ?
C12A N3A C9A N1A 178.8(10) . . . . ?
C9A N2A C10A C11A -30.4(19) . . . . ?
N2A C10A C11A C12A 51.2(18) . . . . ?
C9A N3A C12A C13A 138.0(12) . . . . ?
C9A N3A C12A C11A 18.0(16) . . . . ?
C10A C11A C12A N3A -45.7(18) . . . . ?
C10A C11A C12A C13A -167.2(13) . . . . ?
N3A C12A C13A C14A 61.5(14) . . . . ?
C11A C12A C13A C14A -179.3(11) . . . . ?
N4A C14A C13A C12A -175.6(11) . . . . ?
C15A C14A C13A C12A 75.0(15) . . . . ?
C8B O1B C1B C2B -170.6(10) . . . . ?
O1B C1B C2B C3B -77.3(16) . . . . ?
O1B C1B C2B C7B 101.7(16) . . . . ?
C7B C2B C3B C4B -3(2) . . . . ?
C1B C2B C3B C4B 175.6(14) . . . . ?
C2B C3B C4B C5B 0(2) . . . . ?
C3B C4B C5B C6B 2(3) . . . . ?
C4B C5B C6B C7B 0(3) . . . . ?
C3B C2B C7B C6B 5(2) . . . . ?
C1B C2B C7B C6B -174.1(13) . . . . ?
C5B C6B C7B C2B -3(2) . . . . ?
C1B O1B C8B O2B -3.6(18) . . . . ?
C1B O1B C8B N1B 177.5(12) . . . . ?
C9B N1B C8B O2B 8(2) . . . . ?
C9B N1B C8B O1B -173.1(9) . . . . ?
C10B N2B C9B N1B -176.6(10) . . . . ?
C10B N2B C9B N3B 2.4(18) . . . . ?
C8B N1B C9B N2B -175.5(11) . . . . ?
C8B N1B C9B N3B 5.5(17) . . . . ?
C12B N3B C9B N2B -1.5(17) . . . . ?
C12B N3B C9B N1B 177.4(10) . . . . ?
C9B N2B C10B C11B -28.8(17) . . . . ?
N2B C10B C11B C12B 54.3(14) . . . . ?
C9B N3B C12B C11B 27.0(15) . . . . ?
C9B N3B C12B C13B 148.4(11) . . . . ?
C10B C11B C12B N3B -52.2(14) . . . . ?
C10B C11B C12B C13B -169.1(9) . . . . ?
N3B C12B C13B C14B 159.2(10) . . . . ?
C11B C12B C13B C14B -82.9(14) . . . . ?
C16B N4B C14B C13B -132.0(12) . . . . ?
C16B N4B C14B C15B -13.0(14) . . . . ?
C12B C13B C14B N4B -76.5(14) . . . . ?
C12B C13B C14B C15B 174.3(12) . . . . ?
C16B O3B C15B C14B -12.7(14) . . . . ?
N4B C14B C15B O3B 14.4(12) . . . . ?
C13B C14B C15B O3B 132.3(11) . . . . ?
C14B N4B C16B O4B -175.2(14) . . . . ?
C14B N4B C16B O3B 6.2(15) . . . . ?
C15B O3B C16B O4B -174.2(13) . . . . ?
C15B O3B C16B N4B 4.6(14) . . . . ?
