#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/92/2229228.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2229228
loop_
_publ_author_name
'Gutierrez, Margarita'
'Astudillo, Luis'
'Quesada, Luisa'
'Brito, Iván'
'López-Rodríguez, Matías'
_publ_section_title
;
 1-[2-(4-Nitrophenyl)-5-(5-phenyl-1,2-oxazol-3-yl)-1,2,3,4-tetrahydroquinolin-4-yl]pyrrolidin-2-one
;
_journal_coeditor_code           SJ5084
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o308
_journal_page_last               o309
_journal_paper_doi               10.1107/S1600536810054048
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C28 H24 N4 O4'
_chemical_formula_moiety         'C28 H24 N4 O4'
_chemical_formula_sum            'C28 H24 N4 O4'
_chemical_formula_weight         480.51
_chemical_name_systematic
;
1-[2-(4-Nitrophenyl)-5-(5-phenyl-1,2-oxazol-3-yl)-1,2,3,4-tetrahydroquinolin-
4-yl]pyrrolidin-2-one
;
_space_group_IT_number           169
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 61'
_symmetry_space_group_name_H-M   'P 61'
_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                120.00
_cell_formula_units_Z            6
_cell_length_a                   20.753(3)
_cell_length_b                   20.753(3)
_cell_length_c                   10.446(2)
_cell_measurement_reflns_used    2728
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.77
_cell_volume                     3896.2(11)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) & PLATON (Spek, 2009)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Nonius KappaCCD area-detector diffractometer'
_diffrn_measurement_method       'φ scans, and ω scans with κ  offsets'
_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  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5951
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.77
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1512
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.237
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.215
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         3144
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.215
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0751
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0755P)²+0.8624P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1554
_refine_ls_wR_factor_ref         0.1618
_reflns_number_gt                2646
_reflns_number_total             3144
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5084.cif
_cod_data_source_block           I
_cod_database_code               2229228
_cod_database_fobs_code          2229228
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'x-y, x, z+1/6'
'y, -x+y, z+5/6'
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
O O1 0.2019(3) -0.0999(3) 0.6005(5) 0.1165(18) Uani d . 1 . .
O O2 0.1082(3) -0.1080(3) 0.5004(7) 0.147(3) Uani d . 1 . .
O O3 0.54683(17) 0.55998(14) 0.2252(3) 0.0485(7) Uani d . 1 . .
O O4 0.36115(17) 0.42435(19) 0.2789(3) 0.0607(8) Uani d . 1 . .
N N1 0.1743(3) -0.0784(3) 0.5205(5) 0.0880(15) Uani d . 1 . .
N N2 0.43438(18) 0.19821(17) 0.2011(4) 0.0456(8) Uani d . 1 . .
N N3 0.5569(2) 0.49764(18) 0.2257(4) 0.0492(8) Uani d . 1 . .
N N4 0.36641(16) 0.33963(17) 0.1463(3) 0.0388(7) Uani d . 1 . .
C C1 0.2234(3) -0.0115(2) 0.4445(5) 0.0631(12) Uani d . 1 . .
C C2 0.2982(3) 0.0205(3) 0.4559(5) 0.0637(12) Uani d . 1 . .
H H2 0.3186 -0.0002 0.5098 0.076 Uiso calc R 1 . .
C C3 0.3433(2) 0.0833(2) 0.3881(5) 0.0597(12) Uani d . 1 . .
H H3 0.3946 0.1050 0.3963 0.072 Uiso calc R 1 . .
C C4 0.3145(2) 0.1154(2) 0.3075(4) 0.0489(10) Uani d . 1 . .
C C5 0.2376(3) 0.0806(3) 0.2964(7) 0.0855(19) Uani d . 1 . .
H H5 0.2168 0.1006 0.2416 0.103 Uiso calc R 1 . .
C C6 0.1916(3) 0.0171(3) 0.3647(7) 0.091(2) Uani d . 1 . .
H H6 0.1401 -0.0057 0.3568 0.109 Uiso calc R 1 . .
C C7 0.3612(2) 0.1867(2) 0.2334(5) 0.0471(9) Uani d . 1 . .
H H7 0.3351 0.1839 0.1535 0.057 Uiso calc R 1 . .
C C8 0.3719(2) 0.25488(19) 0.3085(4) 0.0404(8) Uani d . 1 . .
H H8A 0.3237 0.2483 0.3310 0.048 Uiso calc R 1 . .
H H8B 0.3985 0.2591 0.3873 0.048 Uiso calc R 1 . .
C C9 0.41529(18) 0.32633(18) 0.2308(4) 0.0337(7) Uani d . 1 . .
H H9 0.4378 0.3677 0.2918 0.040 Uiso calc R 1 . .
C C10 0.47821(18) 0.32842(19) 0.1526(4) 0.0335(7) Uani d . 1 . .
C C11 0.4825(2) 0.26296(19) 0.1383(4) 0.0379(8) Uani d . 1 . .
C C12 0.5384(2) 0.2653(2) 0.0586(4) 0.0451(10) Uani d . 1 . .
H H12 0.5428 0.2231 0.0502 0.054 Uiso calc R 1 . .
C C13 0.5865(2) 0.3290(2) -0.0069(4) 0.0499(10) Uani d . 1 . .
H H13 0.6217 0.3289 -0.0618 0.060 Uiso calc R 1 . .
C C14 0.5826(2) 0.3935(2) 0.0088(4) 0.0439(9) Uani d . 1 . .
H H14 0.6151 0.4365 -0.0357 0.053 Uiso calc R 1 . .
C C15 0.53053(19) 0.39350(19) 0.0906(4) 0.0345(8) Uani d . 1 . .
C C16 0.53036(18) 0.46432(19) 0.1164(4) 0.0355(8) Uani d . 1 . .
C C17 0.5044(2) 0.5032(2) 0.0404(4) 0.0393(8) Uani d . 1 . .
H H17 0.4844 0.4914 -0.0417 0.047 Uiso calc R 1 . .
C C18 0.51507(19) 0.56076(19) 0.1134(4) 0.0374(8) Uani d . 1 . .
C C19 0.4969(2) 0.6206(2) 0.0963(4) 0.0401(8) Uani d . 1 . .
C C20 0.4578(2) 0.6207(2) -0.0102(4) 0.0456(9) Uani d . 1 . .
H H20 0.4425 0.5828 -0.0704 0.055 Uiso calc R 1 . .
C C21 0.4409(2) 0.6770(3) -0.0284(5) 0.0552(11) Uani d . 1 . .
H H21 0.4141 0.6767 -0.0999 0.066 Uiso calc R 1 . .
C C22 0.4643(3) 0.7329(3) 0.0603(6) 0.0655(14) Uani d . 1 . .
H H22 0.4544 0.7714 0.0476 0.079 Uiso calc R 1 . .
C C23 0.5015(4) 0.7325(3) 0.1657(6) 0.0790(17) Uani d . 1 . .
H H23 0.5157 0.7701 0.2262 0.095 Uiso calc R 1 . .
C C24 0.5191(3) 0.6767(3) 0.1855(5) 0.0671(14) Uani d . 1 . .
H H24 0.5454 0.6773 0.2579 0.080 Uiso calc R 1 . .
C C25 0.3392(3) 0.3060(3) 0.0210(5) 0.0674(14) Uani d . 1 . .
H H25A 0.3053 0.2529 0.0290 0.081 Uiso calc R 1 . .
H H25B 0.3802 0.3141 -0.0341 0.081 Uiso calc R 1 . .
C C26 0.2998(3) 0.3441(4) -0.0316(6) 0.0799(16) Uani d . 1 . .
H H26A 0.3271 0.3753 -0.1038 0.096 Uiso calc R 1 . .
H H26B 0.2503 0.3076 -0.0602 0.096 Uiso calc R 1 . .
C C27 0.2955(3) 0.3900(3) 0.0734(5) 0.0704(14) Uani d . 1 . .
H H27A 0.2446 0.3694 0.1028 0.085 Uiso calc R 1 . .
H H27B 0.3135 0.4407 0.0446 0.085 Uiso calc R 1 . .
C C28 0.3444(2) 0.3884(2) 0.1797(4) 0.0474(10) Uani d . 1 . .
H H2N 0.4315(16) 0.1573(18) 0.174(3) 0.017(8) Uiso 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'
O O 0.0106 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'
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
C18 O3 N3 . . 108.2(3) ?
O2 N1 O1 . . 123.8(5) ?
O2 N1 C1 . . 117.2(5) ?
O1 N1 C1 . . 119.0(5) ?
C11 N2 C7 . . 117.3(3) ?
C11 N2 H2N . . 117(2) ?
C7 N2 H2N . . 111.2(19) ?
C16 N3 O3 . . 105.4(3) ?
C28 N4 C25 . . 113.3(3) ?
C28 N4 C9 . . 120.7(3) ?
C25 N4 C9 . . 126.0(3) ?
C2 C1 C6 . . 121.6(4) ?
C2 C1 N1 . . 119.8(5) ?
C6 C1 N1 . . 118.6(5) ?
C1 C2 C3 . . 119.6(5) ?
C1 C2 H2 . . 120.2 ?
C3 C2 H2 . . 120.2 ?
C2 C3 C4 . . 121.5(4) ?
C2 C3 H3 . . 119.3 ?
C4 C3 H3 . . 119.3 ?
C3 C4 C5 . . 117.5(4) ?
C3 C4 C7 . . 124.3(4) ?
C5 C4 C7 . . 118.2(4) ?
C6 C5 C4 . . 121.4(5) ?
C6 C5 H5 . . 119.3 ?
C4 C5 H5 . . 119.3 ?
C1 C6 C5 . . 118.4(5) ?
C1 C6 H6 . . 120.8 ?
C5 C6 H6 . . 120.8 ?
N2 C7 C4 . . 112.6(3) ?
N2 C7 C8 . . 108.0(3) ?
C4 C7 C8 . . 111.5(4) ?
N2 C7 H7 . . 108.2 ?
C4 C7 H7 . . 108.2 ?
C8 C7 H7 . . 108.2 ?
C9 C8 C7 . . 111.5(3) ?
C9 C8 H8A . . 109.3 ?
C7 C8 H8A . . 109.3 ?
C9 C8 H8B . . 109.3 ?
C7 C8 H8B . . 109.3 ?
H8A C8 H8B . . 108.0 ?
N4 C9 C10 . . 109.5(3) ?
N4 C9 C8 . . 112.0(3) ?
C10 C9 C8 . . 113.2(3) ?
N4 C9 H9 . . 107.3 ?
C10 C9 H9 . . 107.3 ?
C8 C9 H9 . . 107.3 ?
C15 C10 C11 . . 119.2(3) ?
C15 C10 C9 . . 121.1(3) ?
C11 C10 C9 . . 119.6(3) ?
N2 C11 C12 . . 119.9(3) ?
N2 C11 C10 . . 121.7(3) ?
C12 C11 C10 . . 118.4(3) ?
C13 C12 C11 . . 121.2(3) ?
C13 C12 H12 . . 119.4 ?
C11 C12 H12 . . 119.4 ?
C12 C13 C14 . . 120.2(3) ?
C12 C13 H13 . . 119.9 ?
C14 C13 H13 . . 119.9 ?
C15 C14 C13 . . 119.8(4) ?
C15 C14 H14 . . 120.1 ?
C13 C14 H14 . . 120.1 ?
C14 C15 C10 . . 121.1(3) ?
C14 C15 C16 . . 119.9(3) ?
C10 C15 C16 . . 118.9(3) ?
N3 C16 C17 . . 111.6(3) ?
N3 C16 C15 . . 118.0(3) ?
C17 C16 C15 . . 130.4(3) ?
C18 C17 C16 . . 104.4(3) ?
C18 C17 H17 . . 127.8 ?
C16 C17 H17 . . 127.8 ?
C17 C18 O3 . . 110.3(3) ?
C17 C18 C19 . . 133.0(4) ?
O3 C18 C19 . . 116.6(3) ?
C20 C19 C24 . . 119.5(4) ?
C20 C19 C18 . . 119.9(4) ?
C24 C19 C18 . . 120.7(4) ?
C19 C20 C21 . . 120.5(4) ?
C19 C20 H20 . . 119.7 ?
C21 C20 H20 . . 119.7 ?
C22 C21 C20 . . 119.2(4) ?
C22 C21 H21 . . 120.4 ?
C20 C21 H21 . . 120.4 ?
C23 C22 C21 . . 120.6(4) ?
C23 C22 H22 . . 119.7 ?
C21 C22 H22 . . 119.7 ?
C22 C23 C24 . . 121.0(5) ?
C22 C23 H23 . . 119.5 ?
C24 C23 H23 . . 119.5 ?
C19 C24 C23 . . 119.1(5) ?
C19 C24 H24 . . 120.4 ?
C23 C24 H24 . . 120.4 ?
N4 C25 C26 . . 105.1(4) ?
N4 C25 H25A . . 110.7 ?
C26 C25 H25A . . 110.7 ?
N4 C25 H25B . . 110.7 ?
C26 C25 H25B . . 110.7 ?
H25A C25 H25B . . 108.8 ?
C27 C26 C25 . . 107.0(4) ?
C27 C26 H26A . . 110.3 ?
C25 C26 H26A . . 110.3 ?
C27 C26 H26B . . 110.3 ?
C25 C26 H26B . . 110.3 ?
H26A C26 H26B . . 108.6 ?
C26 C27 C28 . . 105.7(4) ?
C26 C27 H27A . . 110.6 ?
C28 C27 H27A . . 110.6 ?
C26 C27 H27B . . 110.6 ?
C28 C27 H27B . . 110.6 ?
H27A C27 H27B . . 108.7 ?
O4 C28 N4 . . 125.3(4) ?
O4 C28 C27 . . 126.7(4) ?
N4 C28 C27 . . 108.0(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
O1 N1 . 1.217(6) ?
O2 N1 . 1.209(7) ?
O3 C18 . 1.344(5) ?
O3 N3 . 1.410(4) ?
O4 C28 . 1.221(5) ?
N1 C1 . 1.477(6) ?
N2 C11 . 1.375(5) ?
N2 C7 . 1.454(5) ?
N2 H2N . 0.87(3) ?
N3 C16 . 1.306(5) ?
N4 C28 . 1.349(5) ?
N4 C25 . 1.457(6) ?
N4 C9 . 1.472(4) ?
C1 C2 . 1.353(7) ?
C1 C6 . 1.370(7) ?
C2 C3 . 1.362(6) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.381(6) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.389(6) ?
C4 C7 . 1.514(6) ?
C5 C6 . 1.378(8) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.534(5) ?
C7 H7 . 0.9800 ?
C8 C9 . 1.527(5) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.523(5) ?
C9 H9 . 0.9800 ?
C10 C15 . 1.398(5) ?
C10 C11 . 1.413(5) ?
C11 C12 . 1.409(6) ?
C12 C13 . 1.375(6) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.390(6) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.378(5) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.496(5) ?
C16 C17 . 1.416(5) ?
C17 C18 . 1.339(5) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.477(5) ?
C19 C20 . 1.378(6) ?
C19 C24 . 1.379(6) ?
C20 C21 . 1.390(6) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.370(7) ?
C21 H21 . 0.9300 ?
C22 C23 . 1.346(8) ?
C22 H22 . 0.9300 ?
C23 C24 . 1.394(7) ?
C23 H23 . 0.9300 ?
C24 H24 . 0.9300 ?
C25 C26 . 1.497(7) ?
C25 H25A . 0.9700 ?
C25 H25B . 0.9700 ?
C26 C27 . 1.486(8) ?
C26 H26A . 0.9700 ?
C26 H26B . 0.9700 ?
C27 C28 . 1.515(7) ?
C27 H27A . 0.9700 ?
C27 H27B . 0.9700 ?
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
N2 H2N O4 6_554 0.87(3) 1.99(3) 2.859(6) 180(5)
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
C18 O3 N3 C16 . . . . -0.6(4) ?
O2 N1 C1 C2 . . . . -174.9(7) ?
O1 N1 C1 C2 . . . . 6.3(8) ?
O2 N1 C1 C6 . . . . 5.8(9) ?
O1 N1 C1 C6 . . . . -173.0(6) ?
C6 C1 C2 C3 . . . . 0.9(8) ?
N1 C1 C2 C3 . . . . -178.4(5) ?
C1 C2 C3 C4 . . . . 0.1(8) ?
C2 C3 C4 C5 . . . . -1.0(8) ?
C2 C3 C4 C7 . . . . 177.5(5) ?
C3 C4 C5 C6 . . . . 1.1(10) ?
C7 C4 C5 C6 . . . . -177.5(6) ?
C2 C1 C6 C5 . . . . -0.8(10) ?
N1 C1 C6 C5 . . . . 178.5(6) ?
C4 C5 C6 C1 . . . . -0.2(11) ?
C11 N2 C7 C4 . . . . -177.3(4) ?
C11 N2 C7 C8 . . . . -53.8(5) ?
C3 C4 C7 N2 . . . . 29.5(6) ?
C5 C4 C7 N2 . . . . -152.0(5) ?
C3 C4 C7 C8 . . . . -92.1(5) ?
C5 C4 C7 C8 . . . . 86.4(6) ?
N2 C7 C8 C9 . . . . 59.0(4) ?
C4 C7 C8 C9 . . . . -176.8(3) ?
C28 N4 C9 C10 . . . . -133.2(3) ?
C25 N4 C9 C10 . . . . 44.6(5) ?
C28 N4 C9 C8 . . . . 100.4(4) ?
C25 N4 C9 C8 . . . . -81.8(5) ?
C7 C8 C9 N4 . . . . 85.5(4) ?
C7 C8 C9 C10 . . . . -38.9(4) ?
N4 C9 C10 C15 . . . . 63.8(4) ?
C8 C9 C10 C15 . . . . -170.5(3) ?
N4 C9 C10 C11 . . . . -114.0(4) ?
C8 C9 C10 C11 . . . . 11.8(5) ?
C7 N2 C11 C12 . . . . -153.3(4) ?
C7 N2 C11 C10 . . . . 27.5(6) ?
C15 C10 C11 N2 . . . . 177.3(3) ?
C9 C10 C11 N2 . . . . -4.9(5) ?
C15 C10 C11 C12 . . . . -1.9(5) ?
C9 C10 C11 C12 . . . . 175.9(3) ?
N2 C11 C12 C13 . . . . 179.0(4) ?
C10 C11 C12 C13 . . . . -1.8(6) ?
C11 C12 C13 C14 . . . . 2.7(6) ?
C12 C13 C14 C15 . . . . 0.2(6) ?
C13 C14 C15 C10 . . . . -4.0(6) ?
C13 C14 C15 C16 . . . . 174.8(4) ?
C11 C10 C15 C14 . . . . 4.8(5) ?
C9 C10 C15 C14 . . . . -173.0(3) ?
C11 C10 C15 C16 . . . . -174.0(3) ?
C9 C10 C15 C16 . . . . 8.2(5) ?
O3 N3 C16 C17 . . . . 1.5(4) ?
O3 N3 C16 C15 . . . . -177.6(3) ?
C14 C15 C16 N3 . . . . -103.9(4) ?
C10 C15 C16 N3 . . . . 74.9(4) ?
C14 C15 C16 C17 . . . . 77.0(5) ?
C10 C15 C16 C17 . . . . -104.2(5) ?
N3 C16 C17 C18 . . . . -1.9(4) ?
C15 C16 C17 C18 . . . . 177.2(4) ?
C16 C17 C18 O3 . . . . 1.4(4) ?
C16 C17 C18 C19 . . . . -176.3(4) ?
N3 O3 C18 C17 . . . . -0.6(4) ?
N3 O3 C18 C19 . . . . 177.6(3) ?
C17 C18 C19 C20 . . . . 4.0(6) ?
O3 C18 C19 C20 . . . . -173.6(3) ?
C17 C18 C19 C24 . . . . -175.8(5) ?
O3 C18 C19 C24 . . . . 6.6(6) ?
C24 C19 C20 C21 . . . . 0.4(6) ?
C18 C19 C20 C21 . . . . -179.4(4) ?
C19 C20 C21 C22 . . . . 0.6(6) ?
C20 C21 C22 C23 . . . . -1.7(8) ?
C21 C22 C23 C24 . . . . 1.9(9) ?
C20 C19 C24 C23 . . . . -0.2(8) ?
C18 C19 C24 C23 . . . . 179.5(5) ?
C22 C23 C24 C19 . . . . -0.9(9) ?
C28 N4 C25 C26 . . . . 4.4(6) ?
C9 N4 C25 C26 . . . . -173.5(4) ?
N4 C25 C26 C27 . . . . -8.6(7) ?
C25 C26 C27 C28 . . . . 9.5(7) ?
C25 N4 C28 O4 . . . . -178.7(4) ?
C9 N4 C28 O4 . . . . -0.7(6) ?
C25 N4 C28 C27 . . . . 1.6(5) ?
C9 N4 C28 C27 . . . . 179.6(4) ?
C26 C27 C28 O4 . . . . 173.3(5) ?
C26 C27 C28 N4 . . . . -7.0(6) ?
