#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/72/2227211.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_2227211
loop_
_publ_author_name
'Li, Qing'
'Wang, Xian-Yu'
'Qin, Cheng-Ming'
'Wang, Yan-Lin'
_publ_section_title
;
 Ethyl
 2-isopropylamino-6-methyl-8-oxo-3-phenyl-3H,8H-furo[2,3-d][1,2,4]triazolo[1,5-a]pyrimidine-7-carboxylate
;
_journal_coeditor_code           BT5323
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2384
_journal_paper_doi               10.1107/S1600536810032654
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C20 H21 N5 O4'
_chemical_formula_moiety         'C20 H21 N5 O4'
_chemical_formula_sum            'C20 H21 N5 O4'
_chemical_formula_weight         395.42
_chemical_name_systematic
;
Ethyl 2-isopropylamino-6-methyl-8-oxo-3-phenyl-3H,8H-
furo[2,3-d][1,2,4]triazolo[1,5-a]pyrimidine-7-carboxylate
;
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_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            16
_cell_length_a                   19.9810(11)
_cell_length_b                   37.3673(19)
_cell_length_c                   10.7181(6)
_cell_measurement_reflns_used    3861
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      20.84
_cell_measurement_theta_min      2.22
_cell_volume                     8002.5(7)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART 4K CCD area-detector'
_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  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       47
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21970
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9906
_exptl_absorpt_correction_T_min  0.9814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3328
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         2074
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0434
_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)+(0.0601P)²+2.4148P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1093
_reflns_number_gt                1883
_reflns_number_total             2074
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5323.cif
_cod_data_source_block           I
_cod_database_code               2227211
_cod_database_fobs_code          2227211
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.25088(16) 0.07862(8) 0.2745(4) 0.0618(8) Uani d . 1 . .
H H1 0.2634 0.0694 0.1974 0.074 Uiso calc R 1 . .
C C2 0.29491(17) 0.07774(9) 0.3748(4) 0.0743(11) Uani d . 1 . .
H H2 0.3378 0.0685 0.3640 0.089 Uiso calc R 1 . .
C C3 0.2759(2) 0.09026(10) 0.4890(4) 0.0829(12) Uani d . 1 . .
H H3 0.3052 0.0889 0.5562 0.099 Uiso calc R 1 . .
C C4 0.2140(2) 0.10476(12) 0.5044(4) 0.0831(11) Uani d . 1 . .
H H4 0.2011 0.1133 0.5822 0.100 Uiso calc R 1 . .
C C5 0.17048(18) 0.10680(10) 0.4059(3) 0.0678(9) Uani d . 1 . .
H H5 0.1287 0.1173 0.4167 0.081 Uiso calc R 1 . .
C C6 0.18834(15) 0.09340(8) 0.2912(3) 0.0520(7) Uani d . 1 . .
C C7 0.07894(14) 0.07677(7) 0.1978(3) 0.0487(6) Uani d . 1 . .
C C8 0.14928(15) 0.10258(7) 0.0675(3) 0.0517(7) Uani d . 1 . .
C C9 0.21415(19) 0.12881(12) -0.1012(4) 0.0790(11) Uani d D 1 . .
H H9A 0.1973 0.1093 -0.1537 0.095 Uiso calc PR 0.76 A 1
H H9B 0.1720 0.1295 -0.1479 0.095 Uiso d PR 0.24 A 2
C C10 0.1741(3) 0.16260(18) -0.1310(7) 0.107(2) Uani d PD 0.76 B 1
H H10A 0.1276 0.1584 -0.1149 0.160 Uiso calc PR 0.76 B 1
H H10B 0.1801 0.1687 -0.2173 0.160 Uiso calc PR 0.76 B 1
H H10C 0.1896 0.1819 -0.0796 0.160 Uiso calc PR 0.76 B 1
C C11 0.2851(3) 0.1340(3) -0.1290(7) 0.137(3) Uani d PD 0.76 B 1
H H11A 0.3032 0.1519 -0.0745 0.205 Uiso calc PR 0.76 B 1
H H11B 0.2901 0.1416 -0.2141 0.205 Uiso calc PR 0.76 B 1
H H11C 0.3086 0.1118 -0.1168 0.205 Uiso calc PR 0.76 B 1
C C11' 0.2599(11) 0.1007(4) -0.153(2) 0.125(8) Uani d PD 0.24 B 2
H H11D 0.2996 0.0995 -0.1023 0.188 Uiso calc PR 0.24 B 2
H H11E 0.2718 0.1067 -0.2367 0.188 Uiso calc PR 0.24 B 2
H H11F 0.2376 0.0780 -0.1514 0.188 Uiso calc PR 0.24 B 2
C C10' 0.2513(12) 0.1649(3) -0.110(3) 0.187(17) Uani d PD 0.24 B 2
H H10D 0.2212 0.1840 -0.0881 0.281 Uiso calc PR 0.24 B 2
H H10E 0.2674 0.1684 -0.1932 0.281 Uiso calc PR 0.24 B 2
H H10F 0.2885 0.1649 -0.0528 0.281 Uiso calc PR 0.24 B 2
C C12 -0.00778(15) 0.06210(8) 0.0432(3) 0.0575(8) Uani d . 1 . .
C C13 -0.03791(14) 0.04496(8) 0.1483(3) 0.0592(8) Uani d . 1 . .
C C14 -0.00908(14) 0.04888(8) 0.2641(3) 0.0549(7) Uani d . 1 . .
C C15 -0.09993(16) 0.02527(8) 0.1723(4) 0.0680(10) Uani d . 1 . .
C C16 -0.10362(17) 0.02052(9) 0.2962(4) 0.0715(10) Uani d . 1 . .
C C17 -0.1520(2) 0.00305(13) 0.3833(5) 0.0982(14) Uani d . 1 . .
H H17A -0.1864 -0.0087 0.3360 0.147 Uiso calc R 1 . .
H H17B -0.1719 0.0209 0.4361 0.147 Uiso calc R 1 . .
H H17C -0.1289 -0.0142 0.4336 0.147 Uiso calc R 1 . .
C C18 -0.1456(2) 0.00781(11) 0.0816(5) 0.0832(12) Uani d . 1 . .
C C19 -0.1552(3) -0.01350(12) -0.1254(6) 0.1117(18) Uani d . 1 . .
H H19A -0.1946 0.0006 -0.1452 0.134 Uiso calc R 1 . .
H H19B -0.1697 -0.0370 -0.0976 0.134 Uiso calc R 1 . .
C C20 -0.1128(4) -0.0169(2) -0.2349(7) 0.158(3) Uani d . 1 . .
H H20A -0.0985 0.0064 -0.2614 0.237 Uiso calc R 1 . .
H H20B -0.1375 -0.0282 -0.3009 0.237 Uiso calc R 1 . .
H H20C -0.0743 -0.0312 -0.2147 0.237 Uiso calc R 1 . .
N N1 0.14054(11) 0.09293(6) 0.1915(2) 0.0506(6) Uani d . 1 . .
N N2 0.05524(11) 0.07635(6) 0.0793(2) 0.0511(6) Uani d . 1 . .
N N3 0.09879(12) 0.09351(6) -0.0029(2) 0.0538(6) Uani d . 1 . .
N N4 0.20563(14) 0.11862(8) 0.0286(3) 0.0636(7) Uani d D 1 B .
H H4A 0.2249(17) 0.1327(8) 0.081(3) 0.076 Uiso d D 1 . .
N N5 0.04897(13) 0.06436(7) 0.2978(2) 0.0568(6) Uani d . 1 . .
O O1 -0.02832(11) 0.06660(6) -0.0623(2) 0.0728(7) Uani d . 1 . .
O O2 -0.04849(11) 0.03475(6) 0.3546(2) 0.0695(6) Uani d . 1 . .
O O3 -0.20042(15) -0.00291(9) 0.1061(4) 0.1254(13) Uani d . 1 . .
O O4 -0.11678(14) 0.00387(7) -0.0285(3) 0.0887(9) Uani d . 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 118.9(3) ?
C6 C1 H1 . . 120.6 ?
C2 C1 H1 . . 120.6 ?
C3 C2 C1 . . 120.7(3) ?
C3 C2 H2 . . 119.7 ?
C1 C2 H2 . . 119.7 ?
C4 C3 C2 . . 119.9(4) ?
C4 C3 H3 . . 120.1 ?
C2 C3 H3 . . 120.1 ?
C3 C4 C5 . . 120.4(4) ?
C3 C4 H4 . . 119.8 ?
C5 C4 H4 . . 119.8 ?
C4 C5 C6 . . 120.3(4) ?
C4 C5 H5 . . 119.9 ?
C6 C5 H5 . . 119.9 ?
C5 C6 C1 . . 119.9(3) ?
C5 C6 N1 . . 119.9(3) ?
C1 C6 N1 . . 120.1(3) ?
N5 C7 N2 . . 127.0(3) ?
N5 C7 N1 . . 127.2(3) ?
N2 C7 N1 . . 105.8(2) ?
N3 C8 N4 . . 125.8(3) ?
N3 C8 N1 . . 112.9(2) ?
N4 C8 N1 . . 121.3(3) ?
N4 C9 C11 . . 110.1(4) ?
N4 C9 C11' . . 103.9(10) ?
N4 C9 C10 . . 110.8(4) ?
C11 C9 C10 . . 110.8(6) ?
C11' C9 C10 . . 145.3(10) ?
N4 C9 C10' . . 110.0(11) ?
C11' C9 C10' . . 107.3(9) ?
N4 C9 H9A . . 108.3 ?
C11 C9 H9A . . 108.3 ?
C10 C9 H9A . . 108.3 ?
C10' C9 H9A . . 141.5 ?
N4 C9 H9B . . 113.3 ?
C11 C9 H9B . . 136.6 ?
C11' C9 H9B . . 110.9 ?
C10' C9 H9B . . 111.1 ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H9B C10 H10B . . 95.8 ?
C9 C10 H10C . . 109.5 ?
H9B C10 H10C . . 147.0 ?
C9 C11 H11A . . 109.5 ?
C9 C11 H11B . . 109.5 ?
C9 C11 H11C . . 109.5 ?
C9 C11' H11D . . 109.5 ?
C9 C11' H11E . . 109.5 ?
H11D C11' H11E . . 109.5 ?
C9 C11' H11F . . 109.5 ?
H11D C11' H11F . . 109.5 ?
H11E C11' H11F . . 109.5 ?
C9 C10' H10D . . 109.5 ?
C9 C10' H10E . . 109.5 ?
H10D C10' H10E . . 109.5 ?
C9 C10' H10F . . 109.5 ?
H10D C10' H10F . . 109.5 ?
H10E C10' H10F . . 109.5 ?
O1 C12 N2 . . 120.1(3) ?
O1 C12 C13 . . 130.8(3) ?
N2 C12 C13 . . 109.1(3) ?
C14 C13 C12 . . 119.1(3) ?
C14 C13 C15 . . 104.5(3) ?
C12 C13 C15 . . 136.1(3) ?
N5 C14 O2 . . 118.4(3) ?
N5 C14 C13 . . 130.4(3) ?
O2 C14 C13 . . 111.1(3) ?
C16 C15 C13 . . 106.7(3) ?
C16 C15 C18 . . 123.8(4) ?
C13 C15 C18 . . 128.8(4) ?
C15 C16 O2 . . 110.9(3) ?
C15 C16 C17 . . 135.3(4) ?
O2 C16 C17 . . 113.8(4) ?
C16 C17 H17A . . 109.5 ?
C16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C16 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
O3 C18 O4 . . 123.9(5) ?
O3 C18 C15 . . 124.5(5) ?
O4 C18 C15 . . 111.5(3) ?
O4 C19 C20 . . 108.0(5) ?
O4 C19 H19A . . 110.1 ?
C20 C19 H19A . . 110.1 ?
O4 C19 H19B . . 110.1 ?
C20 C19 H19B . . 110.1 ?
H19A C19 H19B . . 108.4 ?
C19 C20 H20A . . 109.5 ?
C19 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C19 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C7 N1 C8 . . 105.9(2) ?
C7 N1 C6 . . 124.5(2) ?
C8 N1 C6 . . 128.8(2) ?
C7 N2 N3 . . 111.6(2) ?
C7 N2 C12 . . 124.7(3) ?
N3 N2 C12 . . 123.6(2) ?
C8 N3 N2 . . 103.7(2) ?
C8 N4 C9 . . 120.9(3) ?
C8 N4 H4A . . 116(3) ?
C9 N4 H4A . . 114(3) ?
C7 N5 C14 . . 109.0(3) ?
C14 O2 C16 . . 106.8(3) ?
C18 O4 C19 . . 117.4(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 . 1.378(4) ?
C1 C2 . 1.389(5) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.364(7) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.361(6) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.370(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.374(5) ?
C5 H5 . 0.9300 ?
C6 N1 . 1.434(4) ?
C7 N5 . 1.312(4) ?
C7 N2 . 1.355(4) ?
C7 N1 . 1.373(3) ?
C8 N3 . 1.305(4) ?
C8 N4 . 1.342(4) ?
C8 N1 . 1.387(4) ?
C9 N4 . 1.452(5) ?
C9 C11 . 1.461(7) ?
C9 C11' . 1.496(11) ?
C9 C10 . 1.528(7) ?
C9 C10' . 1.543(11) ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C10 H9B . 1.2497 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C11' H11D . 0.9600 ?
C11' H11E . 0.9600 ?
C11' H11F . 0.9600 ?
C10' H10D . 0.9600 ?
C10' H10E . 0.9600 ?
C10' H10F . 0.9600 ?
C12 O1 . 1.215(4) ?
C12 N2 . 1.421(4) ?
C12 C13 . 1.429(5) ?
C13 C14 . 1.376(5) ?
C13 C15 . 1.464(5) ?
C14 N5 . 1.345(4) ?
C14 O2 . 1.357(4) ?
C15 C16 . 1.342(6) ?
C15 C18 . 1.483(6) ?
C16 O2 . 1.374(4) ?
C16 C17 . 1.494(6) ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C18 O3 . 1.196(5) ?
C18 O4 . 1.321(6) ?
C19 O4 . 1.446(5) ?
C19 C20 . 1.454(9) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 0.9600 ?
N2 N3 . 1.394(3) ?
N4 H4A . 0.86(3) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N4 H4A O1 3 0.86(3) 2.21(2) 2.978(4) 148(3)
C17 H17A O3 . 0.96 2.49 3.132(7) 124.3
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 2.1(5) ?
C1 C2 C3 C4 . . . . -2.0(5) ?
C2 C3 C4 C5 . . . . 0.2(6) ?
C3 C4 C5 C6 . . . . 1.6(6) ?
C4 C5 C6 C1 . . . . -1.5(5) ?
C4 C5 C6 N1 . . . . 174.8(3) ?
C2 C1 C6 C5 . . . . -0.3(5) ?
C2 C1 C6 N1 . . . . -176.6(3) ?
O1 C12 C13 C14 . . . . -168.6(3) ?
N2 C12 C13 C14 . . . . 8.9(4) ?
O1 C12 C13 C15 . . . . 3.6(6) ?
N2 C12 C13 C15 . . . . -178.8(3) ?
C12 C13 C14 N5 . . . . -6.7(5) ?
C15 C13 C14 N5 . . . . 178.9(3) ?
C12 C13 C14 O2 . . . . 172.3(3) ?
C15 C13 C14 O2 . . . . -2.2(3) ?
C14 C13 C15 C16 . . . . 2.1(4) ?
C12 C13 C15 C16 . . . . -170.9(4) ?
C14 C13 C15 C18 . . . . -168.0(3) ?
C12 C13 C15 C18 . . . . 19.0(6) ?
C13 C15 C16 O2 . . . . -1.3(4) ?
C18 C15 C16 O2 . . . . 169.4(3) ?
C13 C15 C16 C17 . . . . -179.8(4) ?
C18 C15 C16 C17 . . . . -9.1(7) ?
C16 C15 C18 O3 . . . . 23.7(6) ?
C13 C15 C18 O3 . . . . -167.7(4) ?
C16 C15 C18 O4 . . . . -153.1(4) ?
C13 C15 C18 O4 . . . . 15.5(5) ?
N5 C7 N1 C8 . . . . -177.7(3) ?
N2 C7 N1 C8 . . . . 2.1(3) ?
N5 C7 N1 C6 . . . . 11.6(5) ?
N2 C7 N1 C6 . . . . -168.6(2) ?
N3 C8 N1 C7 . . . . -0.5(3) ?
N4 C8 N1 C7 . . . . -178.8(3) ?
N3 C8 N1 C6 . . . . 169.5(3) ?
N4 C8 N1 C6 . . . . -8.7(5) ?
C5 C6 N1 C7 . . . . -56.1(4) ?
C1 C6 N1 C7 . . . . 120.2(3) ?
C5 C6 N1 C8 . . . . 135.5(3) ?
C1 C6 N1 C8 . . . . -48.2(4) ?
N5 C7 N2 N3 . . . . 176.9(3) ?
N1 C7 N2 N3 . . . . -3.0(3) ?
N5 C7 N2 C12 . . . . 0.2(5) ?
N1 C7 N2 C12 . . . . -179.6(2) ?
O1 C12 N2 C7 . . . . 171.4(3) ?
C13 C12 N2 C7 . . . . -6.5(4) ?
O1 C12 N2 N3 . . . . -4.9(4) ?
C13 C12 N2 N3 . . . . 177.2(2) ?
N4 C8 N3 N2 . . . . 177.0(3) ?
N1 C8 N3 N2 . . . . -1.2(3) ?
C7 N2 N3 C8 . . . . 2.6(3) ?
C12 N2 N3 C8 . . . . 179.3(2) ?
N3 C8 N4 C9 . . . . 2.3(5) ?
N1 C8 N4 C9 . . . . -179.6(3) ?
C11 C9 N4 C8 . . . . -160.5(6) ?
C11' C9 N4 C8 . . . . -103.2(11) ?
C10 C9 N4 C8 . . . . 76.5(5) ?
C10' C9 N4 C8 . . . . 142.2(10) ?
N2 C7 N5 C14 . . . . 3.4(4) ?
N1 C7 N5 C14 . . . . -176.8(3) ?
O2 C14 N5 C7 . . . . -179.0(3) ?
C13 C14 N5 C7 . . . . -0.1(5) ?
N5 C14 O2 C16 . . . . -179.5(3) ?
C13 C14 O2 C16 . . . . 1.4(3) ?
C15 C16 O2 C14 . . . . 0.0(4) ?
C17 C16 O2 C14 . . . . 178.9(3) ?
O3 C18 O4 C19 . . . . 2.0(6) ?
C15 C18 O4 C19 . . . . 178.8(3) ?
C20 C19 O4 C18 . . . . -176.6(4) ?
