data_2203216
loop_
_publ_author_name
'Ko\;sar, Ba\;sak'
'Albayrak, \,Ci\<gdem'
'Odaba\;so\<glu, Mustafa'
'B\"uy\"ukg\"ung\"or, Orhan'
_publ_section_title
;
4-[(3-Chlorophenyl)diazenyl]-6-methoxy-
2-{[tris(hydroxymethyl)methyl]aminomethylene}cyclohexa-3,5-dien-1(2H)-one
;
_journal_issue                 2
_journal_name_full             'Acta Crystallographica, Section E'
_journal_page_first            o190
_journal_page_last             o192
_journal_volume                60
_journal_year                  2004
_chemical_formula_iupac        'C18 H20 Cl N3 O5'
_chemical_formula_moiety       'C18 H20 Cl N3 O5'
_chemical_formula_sum          'C18 H20 Cl N3 O5'
_chemical_formula_weight       393.82
_chemical_melting_point        496-498
_chemical_name_common          ?
_chemical_name_systematic
;
4-[(3-Chlorophenyl)diazenyl]-6-methoxy-
2-{[tris(hydroxymethyl)methyl]aminomethylene}cyclohexa-3,5-dien-1(2H)-one
;
_symmetry_cell_setting         monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 21/c'
_atom_sites_solution_hydrogens difmap
_atom_sites_solution_primary   direct
_atom_sites_solution_secondary difmap
_cell_angle_alpha              90
_cell_angle_beta               101.144(6)
_cell_angle_gamma              90
_cell_formula_units_Z          4
_cell_length_a                 10.6950(8)
_cell_length_b                 12.3204(10)
_cell_length_c                 14.8486(12)
_cell_measurement_reflns_used  12137
_cell_measurement_temperature  291
_cell_measurement_theta_max    28.32
_cell_measurement_theta_min    1.86
_cell_volume                   1919.7(3)
_computing_cell_refinement     X-AREA
_computing_data_collection     'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction      'X-RED (Stoe & Cie, 2002)'
_computing_molecular_graphics  'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material 'WinGX (Farrugia, 1998)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution  'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature    293(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type 'Stoe IPDS 2'
_diffrn_measurement_method     \w
_diffrn_radiation_monochromator 'plane graphite'
_diffrn_radiation_source       'fine-focus sealed tube'
_diffrn_radiation_type         MoK\a
_diffrn_radiation_wavelength   0.71073
_diffrn_reflns_av_R_equivalents 0.0746
_diffrn_reflns_av_sigmaI/netI  0.0499
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_l_max     18
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_number          13394
_diffrn_reflns_theta_full      26.00
_diffrn_reflns_theta_max       26.00
_diffrn_reflns_theta_min       1.94
_diffrn_standards_decay_%      <2
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_number       0
_exptl_absorpt_coefficient_mu  0.233
_exptl_absorpt_correction_T_max 0.963
_exptl_absorpt_correction_T_min 0.850
_exptl_absorpt_correction_type integration
_exptl_absorpt_process_details '(X-RED; Stoe & Cie, 2002)'
_exptl_crystal_colour          orange
_exptl_crystal_density_diffrn  1.363
_exptl_crystal_density_meas    'not measured'
_exptl_crystal_density_method  'not measured'
_exptl_crystal_description     plate
_exptl_crystal_F_000           824
_exptl_crystal_size_max        0.50
_exptl_crystal_size_mid        0.50
_exptl_crystal_size_min        0.16
_refine_diff_density_max       0.635
_refine_diff_density_min       -0.488
_refine_ls_extinction_coef     ?
_refine_ls_extinction_method   none
_refine_ls_goodness_of_fit_ref 0.940
_refine_ls_hydrogen_treatment  refall
_refine_ls_matrix_type         full
_refine_ls_number_parameters   324
_refine_ls_number_reflns       3776
_refine_ls_number_restraints   0
_refine_ls_restrained_S_all    0.940
_refine_ls_R_factor_all        0.0657
_refine_ls_R_factor_gt         0.0427
_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/[\s^2^(Fo^2^)+(0.0703P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_gt        0.1077
_refine_ls_wR_factor_ref       0.1161
_reflns_number_gt              2571
_reflns_number_total           3776
_reflns_threshold_expression   I>2\s(I)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_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
_atom_site_type_symbol
C1 0.13433(18) 0.72957(16) 0.65642(13) 0.0410(4) Uani d . 1 . . C
C2 0.16422(19) 0.83632(17) 0.64022(14) 0.0440(5) Uani d . 1 . . C
C3 0.1306(2) 0.91626(16) 0.69517(14) 0.0464(5) Uani d . 1 . . C
C4 0.0684(2) 0.89373(19) 0.76638(16) 0.0545(6) Uani d . 1 . . C
C5 0.0367(2) 0.7879(2) 0.78045(17) 0.0606(6) Uani d . 1 . . C
C6 0.0688(2) 0.70593(19) 0.72557(16) 0.0532(5) Uani d . 1 . . C
C7 0.2758(2) 0.58065(16) 0.49854(13) 0.0418(4) Uani d . 1 . . C
C8 0.3566(2) 0.60867(16) 0.44155(13) 0.0433(5) Uani d . 1 . . C
C9 0.40194(18) 0.53031(15) 0.38629(12) 0.0389(4) Uani d . 1 . . C
C10 0.36574(19) 0.41905(15) 0.39086(12) 0.0381(4) Uani d . 1 . . C
C11 0.27705(19) 0.39445(15) 0.45030(12) 0.0401(4) Uani d . 1 . . C
C12 0.2347(2) 0.47114(16) 0.50230(13) 0.0418(4) Uani d . 1 . . C
C13 0.47883(19) 0.56439(16) 0.32441(12) 0.0397(4) Uani d . 1 . . C
C14 0.59204(17) 0.52936(15) 0.19671(12) 0.0364(4) Uani d . 1 . . C
C15 0.6282(2) 0.42291(18) 0.15547(15) 0.0480(5) Uani d . 1 . . C
C16 0.5021(2) 0.59626(17) 0.12506(13) 0.0417(4) Uani d . 1 . . C
C17 0.7151(2) 0.58994(18) 0.23637(15) 0.0449(5) Uani d . 1 . . C
C18 0.1609(3) 0.2513(2) 0.50459(17) 0.0569(6) Uani d . 1 . . C
Cl1 0.17021(7) 1.05007(5) 0.67634(5) 0.0717(2) Uani d . 1 . . Cl
N1 0.16723(16) 0.63944(13) 0.60500(11) 0.0445(4) Uani d . 1 . . N
N2 0.23912(17) 0.66560(13) 0.55063(11) 0.0456(4) Uani d . 1 . . N
N3 0.52193(16) 0.49935(13) 0.26894(10) 0.0387(4) Uani d . 1 . . N
O1 0.40725(14) 0.34422(10) 0.34544(9) 0.0458(3) Uani d . 1 . . O
O2 0.52391(17) 0.35069(12) 0.13317(11) 0.0555(4) Uani d . 1 . . O
O3 0.56250(17) 0.63071(14) 0.05367(10) 0.0556(4) Uani d . 1 . . O
O4 0.69757(15) 0.68903(12) 0.27946(10) 0.0516(4) Uani d . 1 . . O
O5 0.24392(15) 0.28706(11) 0.44664(10) 0.0510(4) Uani d . 1 . . O
H1 0.498(3) 0.432(2) 0.2777(18) 0.081(9) Uiso d . 1 . . H
H2 0.207(2) 0.8569(19) 0.5927(16) 0.057(6) Uiso d . 1 . . H
H4 0.049(2) 0.949(2) 0.8062(17) 0.069(7) Uiso d . 1 . . H
H5 -0.004(3) 0.775(2) 0.835(2) 0.087(8) Uiso d . 1 . . H
H6 0.050(2) 0.632(2) 0.7372(16) 0.063(7) Uiso d . 1 . . H
H8 0.381(2) 0.680(2) 0.4389(15) 0.055(6) Uiso d . 1 . . H
H12 0.176(2) 0.4506(18) 0.5458(14) 0.051(6) Uiso d . 1 . . H
H13 0.5001(19) 0.6411(18) 0.3206(13) 0.044(5) Uiso d . 1 . . H
H15A 0.690(2) 0.386(2) 0.1993(17) 0.067(7) Uiso d . 1 . . H
H15B 0.663(2) 0.4365(19) 0.1003(16) 0.062(7) Uiso d . 1 . . H
H16A 0.427(2) 0.5507(18) 0.0979(14) 0.049(6) Uiso d . 1 . . H
H16B 0.4684(19) 0.6597(18) 0.1522(13) 0.044(5) Uiso d . 1 . . H
H17A 0.756(2) 0.5984(17) 0.1854(14) 0.045(5) Uiso d . 1 . . H
H17B 0.770(2) 0.5435(17) 0.2845(14) 0.047(5) Uiso d . 1 . . H
H18A 0.200(2) 0.2584(19) 0.5703(17) 0.060(6) Uiso d . 1 . . H
H18B 0.144(3) 0.178(3) 0.4868(18) 0.080(8) Uiso d . 1 . . H
H18C 0.077(3) 0.296(3) 0.4899(19) 0.088(9) Uiso d . 1 . . H
H22 0.492(3) 0.361(2) 0.0746(19) 0.074(8) Uiso d . 1 . . H
H33 0.598(3) 0.686(3) 0.069(2) 0.088(10) Uiso d . 1 . . H
H44 0.673(3) 0.737(2) 0.232(2) 0.081(9) Uiso d . 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0415(10) 0.0362(10) 0.0478(10) 0.0016(8) 0.0147(8) -0.0018(8)
C2 0.0476(11) 0.0401(11) 0.0480(11) 0.0024(9) 0.0181(9) -0.0004(9)
C3 0.0485(12) 0.0339(10) 0.0583(11) 0.0029(9) 0.0141(10) -0.0022(9)
C4 0.0616(14) 0.0469(13) 0.0610(13) 0.0081(11) 0.0264(11) -0.0085(10)
C5 0.0713(15) 0.0534(14) 0.0692(14) 0.0048(12) 0.0435(13) 0.0012(11)
C6 0.0584(13) 0.0397(12) 0.0694(14) 0.0010(10) 0.0321(11) 0.0019(10)
C7 0.0519(11) 0.0321(10) 0.0442(9) 0.0012(9) 0.0162(9) -0.0029(8)
C8 0.0595(13) 0.0289(10) 0.0451(10) -0.0033(9) 0.0193(9) -0.0027(8)
C9 0.0482(11) 0.0306(9) 0.0404(9) -0.0016(8) 0.0149(8) -0.0012(7)
C10 0.0485(11) 0.0297(9) 0.0375(9) 0.0011(8) 0.0114(8) -0.0008(7)
C11 0.0501(11) 0.0292(9) 0.0422(9) -0.0033(8) 0.0121(9) 0.0021(8)
C12 0.0510(11) 0.0360(10) 0.0419(9) -0.0018(9) 0.0174(9) 0.0005(8)
C13 0.0504(11) 0.0307(10) 0.0401(9) -0.0029(9) 0.0136(8) -0.0015(8)
C14 0.0423(10) 0.0330(9) 0.0364(9) 0.0005(8) 0.0139(8) 0.0019(7)
C15 0.0572(13) 0.0409(12) 0.0492(11) 0.0080(10) 0.0183(11) -0.0006(9)
C16 0.0487(12) 0.0342(10) 0.0422(10) -0.0013(9) 0.0089(9) 0.0023(8)
C17 0.0443(11) 0.0474(12) 0.0439(10) -0.0044(9) 0.0109(9) 0.0035(9)
C18 0.0727(16) 0.0478(14) 0.0546(13) -0.0202(12) 0.0236(12) 0.0003(11)
Cl1 0.0942(5) 0.0360(3) 0.0923(5) -0.0010(3) 0.0366(4) -0.0023(3)
N1 0.0514(10) 0.0371(9) 0.0499(9) 0.0030(8) 0.0222(8) -0.0021(7)
N2 0.0561(10) 0.0364(9) 0.0488(9) 0.0025(8) 0.0214(8) -0.0039(7)
N3 0.0501(10) 0.0299(9) 0.0396(8) -0.0014(7) 0.0169(7) 0.0015(7)
O1 0.0617(9) 0.0297(7) 0.0511(7) 0.0001(6) 0.0236(6) -0.0041(6)
O2 0.0852(11) 0.0348(8) 0.0492(8) -0.0057(8) 0.0192(8) -0.0052(7)
O3 0.0731(11) 0.0510(10) 0.0416(7) -0.0193(8) 0.0080(7) 0.0075(7)
O4 0.0620(9) 0.0417(8) 0.0480(8) -0.0097(7) 0.0032(7) -0.0011(7)
O5 0.0705(9) 0.0307(7) 0.0590(8) -0.0096(7) 0.0301(7) -0.0025(6)
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 119.77(19) y
C6 C1 N1 . . 116.47(18) y
C2 C1 N1 . . 123.76(17) y
C3 C2 C1 . . 118.88(19) ?
C3 C2 H2 . . 118.1(14) ?
C1 C2 H2 . . 123.0(14) ?
C2 C3 C4 . . 122.1(2) ?
C2 C3 Cl1 . . 119.07(17) ?
C4 C3 Cl1 . . 118.80(16) ?
C5 C4 C3 . . 118.5(2) ?
C5 C4 H4 . . 119.8(15) ?
C3 C4 H4 . . 121.7(15) ?
C4 C5 C6 . . 120.5(2) ?
C4 C5 H5 . . 115.5(16) ?
C6 C5 H5 . . 123.9(17) ?
C1 C6 C5 . . 120.3(2) ?
C1 C6 H6 . . 119.5(14) ?
C5 C6 H6 . . 120.2(14) ?
C8 C7 N2 . . 115.56(17) y
C8 C7 C12 . . 120.08(18) y
N2 C7 C12 . . 124.36(18) y
C7 C8 C9 . . 121.11(19) ?
C7 C8 H8 . . 119.1(14) ?
C9 C8 H8 . . 119.8(14) ?
C13 C9 C8 . . 118.94(18) ?
C13 C9 C10 . . 120.91(17) ?
C8 C9 C10 . . 120.10(17) ?
O1 C10 C9 . . 122.98(17) y
O1 C10 C11 . . 120.59(17) ?
C9 C10 C11 . . 116.44(16) ?
C12 C11 O5 . . 125.83(18) y
C12 C11 C10 . . 122.23(17) ?
O5 C11 C10 . . 111.94(16) ?
C11 C12 C7 . . 119.97(18) ?
C11 C12 H12 . . 120.4(12) ?
C7 C12 H12 . . 119.6(12) ?
N3 C13 C9 . . 123.63(18) y
N3 C13 H13 . . 116.5(12) ?
C9 C13 H13 . . 119.9(12) ?
N3 C14 C17 . . 111.37(15) y
N3 C14 C15 . . 106.31(15) ?
C17 C14 C15 . . 107.91(16) ?
N3 C14 C16 . . 107.59(15) ?
C17 C14 C16 . . 112.56(16) ?
C15 C14 C16 . . 110.95(16) ?
O2 C15 C14 . . 112.57(17) ?
O2 C15 H15A . . 105.9(16) ?
C14 C15 H15A . . 109.3(15) ?
O2 C15 H15B . . 108.9(14) ?
C14 C15 H15B . . 110.9(14) ?
H15A C15 H15B . . 109(2) ?
O3 C16 C14 . . 111.55(17) ?
O3 C16 H16A . . 108.2(12) ?
C14 C16 H16A . . 109.0(12) ?
O3 C16 H16B . . 109.1(12) ?
C14 C16 H16B . . 112.1(11) ?
H16A C16 H16B . . 106.7(17) ?
O4 C17 C14 . . 114.74(17) ?
O4 C17 H17A . . 112.9(13) ?
C14 C17 H17A . . 103.9(12) ?
O4 C17 H17B . . 106.3(12) ?
C14 C17 H17B . . 109.6(12) ?
H17A C17 H17B . . 109.4(17) ?
O5 C18 H18A . . 112.2(13) ?
O5 C18 H18B . . 103.4(16) ?
H18A C18 H18B . . 112(2) ?
O5 C18 H18C . . 108.9(16) ?
H18A C18 H18C . . 110(2) ?
H18B C18 H18C . . 110(2) ?
N2 N1 C1 . . 112.79(16) ?
N1 N2 C7 . . 115.68(17) ?
C13 N3 C14 . . 127.05(16) y
C13 N3 H1 . . 109.8(18) ?
C14 N3 H1 . . 123.0(18) ?
C15 O2 H22 . . 106.4(18) ?
C16 O3 H33 . . 108(2) ?
C17 O4 H44 . . 105.0(17) ?
C11 O5 C18 . . 117.58(17) ?
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 . 1.381(3) ?
C1 C2 . 1.385(3) ?
C1 N1 . 1.430(2) y
C2 C3 . 1.370(3) ?
C2 H2 . 0.94(2) ?
C3 C4 . 1.382(3) ?
C3 Cl1 . 1.738(2) y
C4 C5 . 1.373(3) ?
C4 H4 . 0.95(3) ?
C5 C6 . 1.382(3) ?
C5 H5 . 1.00(3) ?
C6 H6 . 0.96(3) ?
C7 C8 . 1.366(3) y
C7 N2 . 1.402(2) y
C7 C12 . 1.424(3) y
C8 C9 . 1.412(3) y
C8 H8 . 0.92(2) ?
C9 C13 . 1.410(3) y
C9 C10 . 1.430(3) y
C10 O1 . 1.272(2) y
C10 C11 . 1.447(3) ?
C11 C12 . 1.353(3) y
C11 O5 . 1.368(2) ?
C12 H12 . 1.02(2) ?
C13 N3 . 1.296(2) y
C13 H13 . 0.98(2) ?
C14 N3 . 1.470(2) y
C14 C17 . 1.528(3) ?
C14 C15 . 1.529(3) ?
C14 C16 . 1.530(3) ?
C15 O2 . 1.415(3) ?
C15 H15A . 0.95(3) ?
C15 H15B . 0.98(2) ?
C16 O3 . 1.409(2) ?
C16 H16A . 1.00(2) ?
C16 H16B . 0.98(2) ?
C17 O4 . 1.408(3) ?
C17 H17A . 0.95(2) ?
C17 H17B . 1.01(2) ?
C18 O5 . 1.421(3) ?
C18 H18A . 0.99(2) ?
C18 H18B . 0.94(3) ?
C18 H18C . 1.04(3) ?
N1 N2 . 1.260(2) y
N3 H1 . 0.88(3) ?
O2 H22 . 0.88(3) ?
O3 H33 . 0.80(3) ?
O4 H44 . 0.91(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
N3 H1 O1 . 0.88(3) 1.88(3) 2.643(2) 145(3)
O2 H22 O3 3_665 0.88(3) 1.88(3) 2.759(2) 173(3)
O3 H33 O1 2_655 0.80(3) 2.33(3) 3.014(2) 144(3)
O3 H33 O5 2_655 0.80(3) 2.14(3) 2.829(2) 144(3)
O4 H44 O1 2_655 0.91(3) 1.85(3) 2.747(2) 165(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 . . . . 1.7(3) ?
N1 C1 C2 C3 . . . . -178.48(19) ?
C1 C2 C3 C4 . . . . 0.2(3) ?
C1 C2 C3 Cl1 . . . . 178.96(16) ?
C2 C3 C4 C5 . . . . -1.7(4) ?
Cl1 C3 C4 C5 . . . . 179.58(19) ?
C3 C4 C5 C6 . . . . 1.3(4) ?
C2 C1 C6 C5 . . . . -2.1(3) ?
N1 C1 C6 C5 . . . . 178.0(2) ?
C4 C5 C6 C1 . . . . 0.6(4) ?
N2 C7 C8 C9 . . . . 179.20(18) ?
C12 C7 C8 C9 . . . . -0.7(3) ?
C7 C8 C9 C13 . . . . 176.11(19) ?
C7 C8 C9 C10 . . . . -1.4(3) ?
C13 C9 C10 O1 . . . . 5.3(3) ?
C8 C9 C10 O1 . . . . -177.26(18) ?
C13 C9 C10 C11 . . . . -174.34(18) ?
C8 C9 C10 C11 . . . . 3.1(3) ?
O1 C10 C11 C12 . . . . 177.41(18) ?
C9 C10 C11 C12 . . . . -3.0(3) ?
O1 C10 C11 O5 . . . . -2.4(3) ?
C9 C10 C11 O5 . . . . 177.16(16) ?
O5 C11 C12 C7 . . . . -179.17(19) ?
C10 C11 C12 C7 . . . . 1.0(3) ?
C8 C7 C12 C11 . . . . 0.9(3) ?
N2 C7 C12 C11 . . . . -178.96(19) ?
C8 C9 C13 N3 . . . . -177.91(18) ?
C10 C9 C13 N3 . . . . -0.4(3) y
N3 C14 C15 O2 . . . . 48.7(2) ?
C17 C14 C15 O2 . . . . 168.23(17) ?
C16 C14 C15 O2 . . . . -68.0(2) ?
N3 C14 C16 O3 . . . . 178.78(15) ?
C17 C14 C16 O3 . . . . 55.7(2) ?
C15 C14 C16 O3 . . . . -65.3(2) ?
N3 C14 C17 O4 . . . . -62.0(2) ?
C15 C14 C17 O4 . . . . -178.30(17) ?
C16 C14 C17 O4 . . . . 58.9(2) ?
C6 C1 N1 N2 . . . . -172.28(18) ?
C2 C1 N1 N2 . . . . 7.8(3) ?
C1 N1 N2 C7 . . . . 179.53(16) y
C8 C7 N2 N1 . . . . -178.24(18) ?
C12 C7 N2 N1 . . . . 1.6(3) ?
C9 C13 N3 C14 . . . . 173.79(18) ?
C17 C14 N3 C13 . . . . 59.2(2) ?
C15 C14 N3 C13 . . . . 176.47(19) ?
C16 C14 N3 C13 . . . . -64.6(2) ?
C12 C11 O5 C18 . . . . -2.2(3) ?
C10 C11 O5 C18 . . . . 177.67(19) ?