Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806030546/cf2052sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806030546/cf2052Isup2.hkl |
CCDC reference: 620729
Data collection: CAD-4-PC Software (Enraf–Nonius, 1992); cell refinement: CELDIM in CAD-4-PC Software; data reduction: XCAD4 (McArdle & Higgins, 1995); program(s) used to solve structure: OSCAIL (McArdle, 2005) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1993) and ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: OSCAIL.
C13H11N3O4 | Z = 4 |
Mr = 273.25 | F(000) = 568 |
Triclinic, P1 | Dx = 1.427 Mg m−3 |
a = 9.990 (2) Å | Mo Kα radiation, λ = 0.71069 Å |
b = 10.913 (3) Å | Cell parameters from 25 reflections |
c = 12.6758 (19) Å | θ = 12–19° |
α = 81.055 (17)° | µ = 0.11 mm−1 |
β = 78.137 (16)° | T = 293 K |
γ = 70.86 (2)° | Block, light yellow |
V = 1271.8 (5) Å3 | 0.50 × 0.40 × 0.30 mm |
Enraf–Nonius CAD-4 diffractometer | 2078 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.018 |
Graphite monochromator | θmax = 25.0°, θmin = 1.7° |
ω–2θ scans | h = 0→11 |
Absorption correction: ψ scan (ABSCALC in OSCAIL; McArdle & Daly, 1999; North et al., 1968) | k = −12→12 |
Tmin = 0.948, Tmax = 0.968 | l = −14→15 |
4900 measured reflections | 3 standard reflections every 120 min |
4452 independent reflections | intensity decay: 1% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.116 | w = 1/[σ2(Fo2) + (0.0576P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.95 | (Δ/σ)max = 0.021 |
4452 reflections | Δρmax = 0.19 e Å−3 |
364 parameters | Δρmin = −0.17 e Å−3 |
116 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0074 (14) |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) - 4.0650 (0.0068) x + 4.6026 (0.0116) y + 8.2697 (0.0097) z = 3.2735 (0.0022) * 0.0174 (0.0015) N11 * -0.0048 (0.0021) C11 * -0.0114 (0.0024) C12 * -0.0033 (0.0024) C13 * 0.0150 (0.0025) C14 * 0.0049 (0.0021) C15 * -0.0178 (0.0020) C16 Rms deviation of fitted atoms = 0.0122 - 5.0479 (0.0052) x + 2.4594 (0.0056) y + 8.5223 (0.0072) z = 2.9476 (0.0025) Angle to previous plane (with approximate e.s.d.) = 11.93 (0.12) * 0.0364 (0.0015) N11 * 0.0005 (0.0020) C17 * -0.0223 (0.0018) N12 * -0.0174 (0.0020) C18 * -0.0005 (0.0021) C19 * -0.0128 (0.0021) C110 * -0.0157 (0.0021) C111 * -0.0035 (0.0016) C112 * 0.0351 (0.0017) N13 0.0771 (0.0029) O13 0.0202 (0.0034) O14 0.9985 (0.0027) O11 - 1.2198 (0.0026) O12 - 1.3399 (0.0044) C113 Rms deviation of fitted atoms = 0.0205 - 4.6913 (0.0096) x + 1.9681 (0.0113) y + 9.1824 (0.0084) z = 4.9261 (0.0113) Angle to previous plane (with approximate e.s.d.) = 4.98 (0.13) * -0.0099 (0.0014) N21 * 0.0090 (0.0020) C21 * 0.0030 (0.0021) C22 * -0.0001 (0.0021) C23 * -0.0041 (0.0023) C24 * -0.0043 (0.0020) C25 * 0.0064 (0.0020) C26 Rms deviation of fitted atoms = 0.0061 - 6.1184 (0.0066) x + 2.1039 (0.0061) y + 7.1916 (0.0084) z = 3.6755 (0.0084) Angle to previous plane (with approximate e.s.d.) = 11.92 (0.14) * -0.0639 (0.0016) N21 * 0.0139 (0.0021) C27 * -0.0013 (0.0018) N22 * 0.0028 (0.0022) C28 * 0.0127 (0.0023) C29 * 0.0488 (0.0022) C210 * 0.0727 (0.0021) C211 * -0.0581 (0.0017) C212 * -0.0278 (0.0020) N23 0.1325 (0.0035) O23 - 0.2007 (0.0045) O24 0.8574 (0.0030) O21 - 1.3191 (0.0026) O22 - 1.6175 (0.0043) C213 Rms deviation of fitted atoms = 0.0425 |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O11 | 0.08162 (17) | 0.46752 (18) | 0.37646 (14) | 0.0597 (5) | |
N21 | 0.2247 (2) | 0.55210 (19) | 0.53186 (15) | 0.0496 (5) | |
H21 | 0.1646 | 0.5331 | 0.5025 | 0.064* | |
N11 | −0.1946 (2) | 0.25156 (19) | 0.16230 (15) | 0.0488 (5) | |
H11 | −0.1499 | 0.1849 | 0.2013 | 0.063* | |
N22 | 0.3036 (2) | 0.7224 (2) | 0.55787 (15) | 0.0516 (6) | |
O12 | 0.24138 (19) | 0.40186 (19) | 0.22975 (15) | 0.0701 (6) | |
O22 | 0.1838 (2) | 0.93528 (17) | 0.21040 (14) | 0.0650 (5) | |
O14 | −0.0727 (3) | 0.7773 (2) | 0.08089 (19) | 0.0969 (8) | |
O13 | 0.0670 (2) | 0.6852 (2) | 0.19687 (17) | 0.0853 (7) | |
N12 | −0.2027 (2) | 0.46247 (19) | 0.08975 (15) | 0.0500 (5) | |
N13 | −0.0189 (3) | 0.6835 (2) | 0.14154 (19) | 0.0636 (6) | |
O21 | −0.0380 (2) | 1.00928 (19) | 0.30268 (14) | 0.0717 (6) | |
N23 | 0.2540 (3) | 1.0500 (2) | 0.4162 (2) | 0.0794 (8) | |
O23 | 0.1810 (3) | 1.1247 (2) | 0.3545 (2) | 0.1065 (9) | |
O24 | 0.3384 (4) | 1.0803 (2) | 0.4550 (2) | 0.1475 (13) | |
C113 | 0.3565 (3) | 0.3827 (4) | 0.2894 (3) | 0.0894 (11) | |
H13A | 0.3469 | 0.4630 | 0.3167 | 0.125* | |
H13B | 0.4472 | 0.3552 | 0.2423 | 0.125* | |
H13C | 0.3520 | 0.3171 | 0.3488 | 0.125* | |
C16 | −0.3703 (3) | 0.3148 (2) | 0.0365 (2) | 0.0545 (7) | |
H16 | −0.3429 | 0.3881 | 0.0063 | 0.071* | |
C26 | 0.4097 (3) | 0.4549 (3) | 0.64898 (19) | 0.0549 (7) | |
H26 | 0.4309 | 0.5327 | 0.6437 | 0.071* | |
C19 | −0.0578 (3) | 0.5664 (2) | 0.14810 (19) | 0.0476 (6) | |
C210 | 0.1558 (3) | 0.8766 (2) | 0.39393 (19) | 0.0474 (6) | |
C28 | 0.3073 (3) | 0.8432 (3) | 0.5263 (2) | 0.0609 (8) | |
H28 | 0.3598 | 0.8764 | 0.5607 | 0.079* | |
C11 | −0.3026 (2) | 0.2321 (2) | 0.11732 (18) | 0.0444 (6) | |
C12 | −0.3422 (3) | 0.1230 (3) | 0.1578 (2) | 0.0686 (8) | |
H12 | −0.2964 | 0.0657 | 0.2110 | 0.089* | |
C111 | −0.0437 (3) | 0.3503 (2) | 0.21705 (19) | 0.0469 (6) | |
H111 | −0.0061 | 0.2741 | 0.2598 | 0.061* | |
C212 | 0.0870 (3) | 0.9510 (2) | 0.2988 (2) | 0.0517 (7) | |
C110 | 0.0026 (2) | 0.4550 (2) | 0.21460 (18) | 0.0434 (6) | |
C17 | −0.1483 (2) | 0.3567 (2) | 0.15515 (18) | 0.0428 (6) | |
C213 | 0.1345 (3) | 0.9955 (3) | 0.1094 (2) | 0.0802 (10) | |
H23A | 0.0536 | 0.9700 | 0.1026 | 0.112* | |
H23B | 0.2107 | 0.9679 | 0.0500 | 0.112* | |
H23C | 0.1067 | 1.0886 | 0.1087 | 0.112* | |
C23 | 0.3488 (4) | 0.2245 (3) | 0.6666 (2) | 0.0779 (9) | |
H23 | 0.3281 | 0.1463 | 0.6728 | 0.101* | |
C24 | 0.4539 (3) | 0.2324 (3) | 0.7181 (2) | 0.0779 (9) | |
H24 | 0.5041 | 0.1600 | 0.7590 | 0.101* | |
C14 | −0.5187 (3) | 0.1805 (3) | 0.0423 (3) | 0.0761 (9) | |
H14 | −0.5920 | 0.1637 | 0.0179 | 0.099* | |
C211 | 0.1481 (2) | 0.7538 (2) | 0.42669 (19) | 0.0480 (6) | |
H211 | 0.0917 | 0.7208 | 0.3960 | 0.062* | |
C112 | 0.1117 (3) | 0.4448 (2) | 0.2832 (2) | 0.0476 (6) | |
C22 | 0.2742 (3) | 0.3316 (3) | 0.6058 (2) | 0.0598 (7) | |
H22 | 0.2037 | 0.3255 | 0.5709 | 0.078* | |
C25 | 0.4834 (3) | 0.3462 (3) | 0.7088 (2) | 0.0659 (8) | |
H25 | 0.5547 | 0.3513 | 0.7433 | 0.086* | |
C27 | 0.2262 (2) | 0.6769 (2) | 0.50743 (18) | 0.0437 (6) | |
C21 | 0.3041 (2) | 0.4476 (2) | 0.59690 (18) | 0.0456 (6) | |
C15 | −0.4786 (3) | 0.2881 (3) | 0.0008 (2) | 0.0651 (8) | |
H15 | −0.5249 | 0.3448 | −0.0525 | 0.085* | |
C18 | −0.1571 (3) | 0.5642 (2) | 0.08795 (19) | 0.0527 (7) | |
H18 | −0.1946 | 0.6386 | 0.0433 | 0.069* | |
C13 | −0.4497 (4) | 0.0973 (3) | 0.1203 (3) | 0.0884 (11) | |
H13 | −0.4753 | 0.0226 | 0.1483 | 0.115* | |
C29 | 0.2385 (3) | 0.9216 (2) | 0.4461 (2) | 0.0535 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O11 | 0.0492 (11) | 0.0863 (14) | 0.0488 (11) | −0.0202 (9) | −0.0119 (9) | −0.0180 (10) |
N21 | 0.0477 (13) | 0.0548 (14) | 0.0513 (13) | −0.0182 (10) | −0.0235 (10) | 0.0060 (10) |
N11 | 0.0546 (13) | 0.0428 (12) | 0.0516 (13) | −0.0104 (10) | −0.0264 (11) | 0.0016 (10) |
N22 | 0.0650 (14) | 0.0503 (14) | 0.0428 (12) | −0.0142 (11) | −0.0228 (11) | −0.0033 (10) |
O12 | 0.0427 (11) | 0.1039 (16) | 0.0643 (12) | −0.0141 (10) | −0.0081 (10) | −0.0292 (11) |
O22 | 0.0663 (12) | 0.0661 (12) | 0.0480 (11) | 0.0009 (10) | −0.0178 (10) | 0.0020 (9) |
O14 | 0.139 (2) | 0.0701 (15) | 0.1004 (17) | −0.0513 (14) | −0.0586 (16) | 0.0294 (13) |
O13 | 0.1049 (17) | 0.0816 (15) | 0.0930 (16) | −0.0490 (13) | −0.0438 (14) | 0.0036 (12) |
N12 | 0.0563 (14) | 0.0479 (13) | 0.0477 (13) | −0.0143 (11) | −0.0218 (11) | 0.0040 (10) |
N13 | 0.0788 (17) | 0.0636 (16) | 0.0554 (15) | −0.0294 (14) | −0.0179 (13) | −0.0001 (12) |
O21 | 0.0580 (12) | 0.0760 (13) | 0.0618 (13) | 0.0088 (10) | −0.0234 (10) | 0.0036 (10) |
N23 | 0.117 (2) | 0.0459 (15) | 0.0875 (19) | −0.0184 (15) | −0.0579 (17) | −0.0034 (13) |
O23 | 0.156 (2) | 0.0534 (13) | 0.130 (2) | −0.0294 (14) | −0.0943 (18) | 0.0243 (13) |
O24 | 0.233 (3) | 0.0732 (16) | 0.195 (3) | −0.0706 (19) | −0.154 (3) | 0.0266 (17) |
C113 | 0.0438 (17) | 0.136 (3) | 0.096 (2) | −0.0203 (18) | −0.0167 (17) | −0.041 (2) |
C16 | 0.0614 (17) | 0.0549 (16) | 0.0526 (16) | −0.0189 (14) | −0.0231 (14) | −0.0008 (13) |
C26 | 0.0531 (16) | 0.0578 (17) | 0.0510 (16) | −0.0144 (13) | −0.0173 (14) | 0.0090 (13) |
C19 | 0.0536 (16) | 0.0476 (16) | 0.0440 (15) | −0.0174 (12) | −0.0085 (13) | −0.0067 (12) |
C210 | 0.0491 (15) | 0.0448 (15) | 0.0425 (14) | −0.0027 (12) | −0.0135 (12) | −0.0045 (12) |
C28 | 0.079 (2) | 0.0521 (18) | 0.0596 (18) | −0.0159 (15) | −0.0317 (16) | −0.0105 (14) |
C11 | 0.0452 (15) | 0.0461 (15) | 0.0418 (14) | −0.0105 (12) | −0.0105 (12) | −0.0071 (12) |
C12 | 0.090 (2) | 0.0588 (19) | 0.0685 (19) | −0.0305 (17) | −0.0368 (17) | 0.0093 (15) |
C111 | 0.0492 (15) | 0.0448 (14) | 0.0439 (14) | −0.0039 (12) | −0.0181 (12) | −0.0047 (11) |
C212 | 0.0590 (18) | 0.0435 (15) | 0.0496 (17) | −0.0055 (13) | −0.0194 (15) | −0.0045 (12) |
C110 | 0.0420 (14) | 0.0481 (15) | 0.0393 (14) | −0.0100 (12) | −0.0075 (12) | −0.0090 (12) |
C17 | 0.0441 (14) | 0.0443 (15) | 0.0364 (13) | −0.0053 (12) | −0.0103 (12) | −0.0068 (11) |
C213 | 0.099 (2) | 0.077 (2) | 0.0460 (17) | 0.0011 (18) | −0.0223 (17) | 0.0030 (15) |
C23 | 0.104 (3) | 0.0462 (18) | 0.079 (2) | −0.0214 (17) | −0.019 (2) | 0.0088 (16) |
C24 | 0.089 (2) | 0.063 (2) | 0.064 (2) | −0.0042 (18) | −0.0214 (18) | 0.0141 (16) |
C14 | 0.076 (2) | 0.076 (2) | 0.094 (2) | −0.0334 (18) | −0.0380 (19) | −0.0070 (19) |
C211 | 0.0452 (15) | 0.0522 (16) | 0.0480 (15) | −0.0126 (12) | −0.0164 (13) | −0.0026 (12) |
C112 | 0.0473 (17) | 0.0481 (16) | 0.0489 (17) | −0.0129 (13) | −0.0103 (13) | −0.0093 (13) |
C22 | 0.0695 (19) | 0.0517 (17) | 0.0594 (18) | −0.0193 (14) | −0.0149 (15) | −0.0011 (14) |
C25 | 0.0635 (19) | 0.069 (2) | 0.0570 (18) | −0.0088 (16) | −0.0209 (15) | 0.0085 (15) |
C27 | 0.0455 (14) | 0.0448 (15) | 0.0402 (14) | −0.0114 (11) | −0.0123 (12) | −0.0005 (11) |
C21 | 0.0437 (15) | 0.0473 (15) | 0.0401 (14) | −0.0089 (12) | −0.0070 (12) | 0.0011 (11) |
C15 | 0.0661 (19) | 0.0653 (19) | 0.072 (2) | −0.0180 (15) | −0.0363 (16) | −0.0013 (15) |
C18 | 0.0585 (17) | 0.0497 (16) | 0.0490 (16) | −0.0133 (13) | −0.0200 (14) | 0.0058 (12) |
C13 | 0.116 (3) | 0.073 (2) | 0.100 (3) | −0.058 (2) | −0.042 (2) | 0.0162 (19) |
C29 | 0.0710 (18) | 0.0374 (15) | 0.0527 (16) | −0.0073 (13) | −0.0251 (14) | −0.0069 (12) |
O11—C112 | 1.202 (3) | C210—C211 | 1.362 (3) |
N21—C27 | 1.353 (3) | C210—C29 | 1.398 (3) |
N21—C21 | 1.412 (3) | C210—C212 | 1.501 (3) |
N21—H21 | 0.860 | C28—C29 | 1.367 (3) |
N11—C17 | 1.355 (3) | C28—H28 | 0.930 |
N11—C11 | 1.406 (3) | C11—C12 | 1.369 (3) |
N11—H11 | 0.860 | C12—C13 | 1.380 (4) |
N22—C28 | 1.327 (3) | C12—H12 | 0.930 |
N22—C27 | 1.345 (3) | C111—C110 | 1.361 (3) |
O12—C112 | 1.303 (3) | C111—C17 | 1.409 (3) |
O12—C113 | 1.445 (3) | C111—H111 | 0.930 |
O22—C212 | 1.314 (3) | C110—C112 | 1.495 (3) |
O22—C213 | 1.449 (3) | C213—H23A | 0.960 |
O14—N13 | 1.221 (3) | C213—H23B | 0.960 |
O13—N13 | 1.221 (3) | C213—H23C | 0.960 |
N12—C18 | 1.326 (3) | C23—C24 | 1.376 (4) |
N12—C17 | 1.338 (3) | C23—C22 | 1.378 (4) |
N13—C19 | 1.439 (3) | C23—H23 | 0.930 |
O21—C212 | 1.196 (3) | C24—C25 | 1.350 (4) |
N23—O23 | 1.206 (3) | C24—H24 | 0.930 |
N23—O24 | 1.211 (3) | C14—C15 | 1.359 (4) |
N23—C29 | 1.443 (3) | C14—C13 | 1.367 (4) |
C113—H13A | 0.960 | C14—H14 | 0.930 |
C113—H13B | 0.960 | C211—C27 | 1.411 (3) |
C113—H13C | 0.960 | C211—H211 | 0.930 |
C16—C15 | 1.381 (3) | C112—O11 | 1.202 (3) |
C16—C11 | 1.385 (3) | C22—C21 | 1.377 (3) |
C16—H16 | 0.930 | C22—H22 | 0.930 |
C26—C25 | 1.379 (3) | C25—H25 | 0.930 |
C26—C21 | 1.383 (3) | C15—H15 | 0.930 |
C26—H26 | 0.930 | C18—H18 | 0.930 |
C19—C18 | 1.378 (3) | C13—H13 | 0.930 |
C19—C110 | 1.401 (3) | ||
C27—N21—C21 | 131.5 (2) | C19—C110—C112 | 124.5 (2) |
C27—N21—H21 | 114.2 | N12—C17—N11 | 119.3 (2) |
C21—N21—H21 | 114.2 | N12—C17—C111 | 122.3 (2) |
C17—N11—C11 | 131.49 (19) | N11—C17—C111 | 118.5 (2) |
C17—N11—H11 | 114.3 | O22—C213—H23A | 109.5 |
C11—N11—H11 | 114.3 | O22—C213—H23B | 109.5 |
C28—N22—C27 | 117.0 (2) | H23A—C213—H23B | 109.5 |
C112—O12—C113 | 115.8 (2) | O22—C213—H23C | 109.5 |
C212—O22—C213 | 116.9 (2) | H23A—C213—H23C | 109.5 |
C18—N12—C17 | 117.0 (2) | H23B—C213—H23C | 109.5 |
O13—N13—O14 | 122.5 (3) | C24—C23—C22 | 120.4 (3) |
O13—N13—C19 | 118.6 (2) | C24—C23—H23 | 119.8 |
O14—N13—C19 | 118.9 (2) | C22—C23—H23 | 119.8 |
O23—N23—O24 | 121.8 (3) | C25—C24—C23 | 119.5 (3) |
O23—N23—C29 | 119.1 (2) | C25—C24—H24 | 120.3 |
O24—N23—C29 | 119.0 (2) | C23—C24—H24 | 120.3 |
O12—C113—H13A | 109.5 | C15—C14—C13 | 119.1 (3) |
O12—C113—H13B | 109.5 | C15—C14—H14 | 120.5 |
H13A—C113—H13B | 109.5 | C13—C14—H14 | 120.5 |
O12—C113—H13C | 109.5 | C210—C211—C27 | 119.7 (2) |
H13A—C113—H13C | 109.5 | C210—C211—H211 | 120.2 |
H13B—C113—H13C | 109.5 | C27—C211—H211 | 120.2 |
C15—C16—C11 | 119.7 (3) | O11—C112—O12 | 125.5 (2) |
C15—C16—H16 | 120.1 | O11—C112—O12 | 125.5 (2) |
C11—C16—H16 | 120.1 | O11—C112—C110 | 123.7 (2) |
C25—C26—C21 | 119.6 (3) | O11—C112—C110 | 123.7 (2) |
C25—C26—H26 | 120.2 | O12—C112—C110 | 110.7 (2) |
C21—C26—H26 | 120.2 | C21—C22—C23 | 119.9 (3) |
C18—C19—C110 | 119.4 (2) | C21—C22—H22 | 120.0 |
C18—C19—N13 | 119.2 (2) | C23—C22—H22 | 120.0 |
C110—C19—N13 | 121.4 (2) | C24—C25—C26 | 121.2 (3) |
C211—C210—C29 | 117.1 (2) | C24—C25—H25 | 119.4 |
C211—C210—C212 | 119.0 (2) | C26—C25—H25 | 119.4 |
C29—C210—C212 | 123.7 (2) | N22—C27—N21 | 119.7 (2) |
N22—C28—C29 | 123.9 (2) | N22—C27—C211 | 122.4 (2) |
N22—C28—H28 | 118.1 | N21—C27—C211 | 117.9 (2) |
C29—C28—H28 | 118.1 | C22—C21—C26 | 119.3 (2) |
C12—C11—C16 | 118.8 (2) | C22—C21—N21 | 116.5 (2) |
C12—C11—N11 | 116.5 (2) | C26—C21—N21 | 124.1 (2) |
C16—C11—N11 | 124.7 (2) | C14—C15—C16 | 121.2 (3) |
C11—C12—C13 | 120.6 (3) | C14—C15—H15 | 119.4 |
C11—C12—H12 | 119.7 | C16—C15—H15 | 119.4 |
C13—C12—H12 | 119.7 | N12—C18—C19 | 124.1 (2) |
C110—C111—C17 | 120.3 (2) | N12—C18—H18 | 118.0 |
C110—C111—H111 | 119.8 | C19—C18—H18 | 118.0 |
C17—C111—H111 | 119.8 | C14—C13—C12 | 120.6 (3) |
O21—C212—O22 | 125.6 (2) | C14—C13—H13 | 119.7 |
O21—C212—C210 | 125.0 (3) | C12—C13—H13 | 119.7 |
O22—C212—C210 | 109.4 (2) | C28—C29—C210 | 120.0 (2) |
C111—C110—C19 | 116.9 (2) | C28—C29—N23 | 119.0 (2) |
C111—C110—C112 | 118.5 (2) | C210—C29—N23 | 121.1 (2) |
O13—N13—C19—C18 | 178.5 (2) | C111—C110—C112—O11 | −86.3 (3) |
O14—N13—C19—C18 | −1.6 (4) | C19—C110—C112—O11 | 92.8 (3) |
O13—N13—C19—C110 | −1.2 (4) | C111—C110—C112—O12 | 90.4 (3) |
O14—N13—C19—C110 | 178.7 (2) | C19—C110—C112—O12 | −90.6 (3) |
C27—N22—C28—C29 | −0.4 (4) | C24—C23—C22—C21 | −0.3 (4) |
C15—C16—C11—C12 | 2.0 (4) | C23—C24—C25—C26 | 0.3 (5) |
C15—C16—C11—N11 | −177.9 (2) | C21—C26—C25—C24 | −0.4 (4) |
C17—N11—C11—C12 | −167.2 (3) | C28—N22—C27—N21 | 176.4 (2) |
C17—N11—C11—C16 | 12.7 (4) | C28—N22—C27—C211 | −1.9 (4) |
C16—C11—C12—C13 | −1.3 (4) | C21—N21—C27—N22 | −7.4 (4) |
N11—C11—C12—C13 | 178.6 (3) | C21—N21—C27—C211 | 170.9 (2) |
C213—O22—C212—O21 | 1.0 (4) | C210—C211—C27—N22 | 3.3 (4) |
C213—O22—C212—C210 | 177.1 (2) | C210—C211—C27—N21 | −175.0 (2) |
C211—C210—C212—O21 | 81.5 (3) | C23—C22—C21—C26 | 0.3 (4) |
C29—C210—C212—O21 | −104.1 (3) | C23—C22—C21—N21 | 179.0 (2) |
C211—C210—C212—O22 | −94.7 (3) | C25—C26—C21—C22 | 0.1 (4) |
C29—C210—C212—O22 | 79.7 (3) | C25—C26—C21—N21 | −178.5 (2) |
C17—C111—C110—C19 | −0.3 (3) | C27—N21—C21—C22 | 179.2 (2) |
C17—C111—C110—C112 | 178.8 (2) | C27—N21—C21—C26 | −2.1 (4) |
C18—C19—C110—C111 | −1.2 (3) | C13—C14—C15—C16 | −0.3 (5) |
N13—C19—C110—C111 | 178.5 (2) | C11—C16—C15—C14 | −1.2 (4) |
C18—C19—C110—C112 | 179.7 (2) | C17—N12—C18—C19 | 0.5 (4) |
N13—C19—C110—C112 | −0.6 (4) | C110—C19—C18—N12 | 1.2 (4) |
C18—N12—C17—N11 | 178.1 (2) | N13—C19—C18—N12 | −178.6 (2) |
C18—N12—C17—C111 | −2.1 (3) | C15—C14—C13—C12 | 1.0 (5) |
C11—N11—C17—N12 | −5.2 (4) | C11—C12—C13—C14 | −0.2 (5) |
C11—N11—C17—C111 | 175.0 (2) | N22—C28—C29—C210 | 1.4 (4) |
C110—C111—C17—N12 | 2.1 (4) | N22—C28—C29—N23 | −178.0 (3) |
C110—C111—C17—N11 | −178.1 (2) | C211—C210—C29—C28 | 0.0 (4) |
C22—C23—C24—C25 | 0.0 (5) | C212—C210—C29—C28 | −174.5 (2) |
C29—C210—C211—C27 | −2.2 (3) | C211—C210—C29—N23 | 179.4 (2) |
C212—C210—C211—C27 | 172.6 (2) | C212—C210—C29—N23 | 4.9 (4) |
C113—O12—C112—O11 | −1.0 (4) | O23—N23—C29—C28 | −171.7 (3) |
C113—O12—C112—O11 | −1.0 (4) | O24—N23—C29—C28 | 7.1 (4) |
C113—O12—C112—C110 | −177.5 (2) | O23—N23—C29—C210 | 8.9 (4) |
C111—C110—C112—O11 | −86.3 (3) | O24—N23—C29—C210 | −172.3 (3) |
C19—C110—C112—O11 | 92.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N21—H21···O11 | 0.86 | 2.25 | 3.060 (3) | 158 |
N21—H21···O11i | 0.86 | 2.62 | 3.107 (3) | 117 |
N11—H11···O21ii | 0.86 | 2.23 | 3.094 (3) | 179 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, y−1, z. |