Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805003491/tk6206sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805003491/tk6206Isup2.hkl |
CCDC reference: 269874
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.009 Å
- R factor = 0.062
- wR factor = 0.188
- Data-to-parameter ratio = 13.0
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.28 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.30 Ratio PLAT430_ALERT_2_B Short Inter D...A Contact O3 .. O4 .. 2.82 Ang.
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 41 Perc. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293 PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.81 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C26 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C27 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C24 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.06 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.69 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C24 H25 N5 O11 Atom count from _chemical_formula_moiety:C0.135 H0.117 N.036 O.099
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.
C9H11NO2·C9H12NO2+·C6H2N3O7− | Z = 2 |
Mr = 559.49 | F(000) = 584 |
Triclinic, P1 | Dx = 1.382 Mg m−3 Dm = 1.38 Mg m−3 Dm measured by flotation, using a mixture of carbon tetrachloride and xylene |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.333 (3) Å | Cell parameters from 25 reflections |
b = 13.737 (3) Å | θ = 8.4–13.9° |
c = 15.381 (6) Å | µ = 0.11 mm−1 |
α = 113.04 (2)° | T = 293 K |
β = 94.93 (4)° | Needle, yellow |
γ = 105.23 (3)° | 0.3 × 0.2 × 0.12 mm |
V = 1344.2 (9) Å3 |
Enraf-Nonius MACH3 diffractometer | 1945 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.048 |
Graphite monochromator | θmax = 25.0°, θmin = 2.7° |
ω/2θ scans | h = −1→8 |
Absorption correction: ψ scan (North et al., 1968) | k = −16→16 |
Tmin = 0.974, Tmax = 0.987 | l = −18→18 |
6021 measured reflections | 3 standard reflections every 60 min |
4724 independent reflections | intensity decay: none |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.188 | H-atom parameters constrained |
S = 0.93 | w = 1/[σ2(Fo2) + (0.0907P)2 + 0.223P] where P = (Fo2 + 2Fc2)/3 |
4724 reflections | (Δ/σ)max < 0.001 |
362 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
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. |
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 | ||
C11 | 0.4139 (6) | 0.3356 (4) | 0.4255 (3) | 0.0445 (12) | |
C12 | 0.2714 (6) | 0.3364 (4) | 0.3477 (3) | 0.0396 (11) | |
H12 | 0.3387 | 0.3442 | 0.2973 | 0.047* | |
C13 | 0.1045 (7) | 0.2256 (4) | 0.3024 (3) | 0.0528 (13) | |
H13A | 0.1567 | 0.1667 | 0.2996 | 0.063* | |
H13B | 0.0150 | 0.2293 | 0.3456 | 0.063* | |
C14 | −0.0078 (7) | 0.1922 (4) | 0.2040 (3) | 0.0471 (12) | |
C15 | −0.2067 (8) | 0.1684 (4) | 0.1856 (5) | 0.0715 (17) | |
H15 | −0.2711 | 0.1800 | 0.2364 | 0.086* | |
C16 | −0.3104 (10) | 0.1274 (5) | 0.0918 (7) | 0.102 (3) | |
H16 | −0.4442 | 0.1103 | 0.0795 | 0.122* | |
C17 | −0.2133 (16) | 0.1120 (6) | 0.0164 (6) | 0.112 (3) | |
H17 | −0.2825 | 0.0845 | −0.0465 | 0.134* | |
C18 | −0.0213 (13) | 0.1364 (5) | 0.0335 (5) | 0.096 (2) | |
H18 | 0.0428 | 0.1263 | −0.0173 | 0.115* | |
C19 | 0.0818 (8) | 0.1767 (4) | 0.1266 (4) | 0.0648 (15) | |
H19 | 0.2155 | 0.1940 | 0.1375 | 0.078* | |
N11 | 0.2005 (5) | 0.4331 (3) | 0.3902 (2) | 0.0415 (9) | |
H11A | 0.1181 | 0.4335 | 0.3444 | 0.062* | |
H11B | 0.3001 | 0.4963 | 0.4147 | 0.062* | |
H11C | 0.1408 | 0.4276 | 0.4369 | 0.062* | |
O1A | 0.4255 (4) | 0.3925 (3) | 0.5116 (2) | 0.0459 (8) | |
O1B | 0.5107 (5) | 0.2705 (3) | 0.3912 (2) | 0.0756 (11) | |
C21 | −0.1004 (6) | 0.3086 (4) | 0.5383 (3) | 0.0378 (11) | |
C22 | 0.0165 (6) | 0.2786 (3) | 0.6027 (3) | 0.0367 (11) | |
H22 | −0.0551 | 0.2711 | 0.6520 | 0.044* | |
C23 | 0.0475 (7) | 0.1673 (4) | 0.5456 (3) | 0.0482 (12) | |
H23A | −0.0777 | 0.1104 | 0.5134 | 0.058* | |
H23B | 0.1163 | 0.1737 | 0.4960 | 0.058* | |
C24 | 0.1573 (7) | 0.1298 (4) | 0.6052 (4) | 0.0520 (13) | |
C25 | 0.3428 (9) | 0.1278 (5) | 0.5949 (6) | 0.095 (2) | |
H25 | 0.3993 | 0.1510 | 0.5514 | 0.115* | |
C26 | 0.4429 (12) | 0.0916 (7) | 0.6491 (9) | 0.151 (4) | |
H26 | 0.5659 | 0.0888 | 0.6409 | 0.181* | |
C27 | 0.3641 (18) | 0.0599 (8) | 0.7146 (9) | 0.157 (5) | |
H27 | 0.4355 | 0.0380 | 0.7521 | 0.189* | |
C28 | 0.1835 (16) | 0.0598 (6) | 0.7258 (5) | 0.117 (3) | |
H28 | 0.1294 | 0.0366 | 0.7698 | 0.141* | |
C29 | 0.0792 (9) | 0.0950 (4) | 0.6706 (4) | 0.0719 (17) | |
H29 | −0.0453 | 0.0950 | 0.6780 | 0.086* | |
N22 | 0.2025 (5) | 0.3708 (3) | 0.6524 (2) | 0.0391 (9) | |
H22A | 0.2727 | 0.3535 | 0.6907 | 0.059* | |
H22B | 0.1792 | 0.4335 | 0.6876 | 0.059* | |
H22C | 0.2672 | 0.3808 | 0.6085 | 0.059* | |
O2A | −0.0340 (4) | 0.3870 (3) | 0.5198 (2) | 0.0490 (8) | |
O2B | −0.2769 (5) | 0.2407 (3) | 0.5056 (3) | 0.0639 (10) | |
H2B | −0.3378 | 0.2606 | 0.4722 | 0.096* | |
C1 | 0.1535 (6) | 0.4625 (4) | 0.1287 (3) | 0.0362 (10) | |
C2 | 0.1551 (6) | 0.4239 (4) | 0.0324 (3) | 0.0390 (11) | |
H2 | 0.2718 | 0.4400 | 0.0130 | 0.047* | |
C3 | −0.0131 (6) | 0.3617 (4) | −0.0360 (3) | 0.0367 (10) | |
C4 | −0.1903 (6) | 0.3415 (3) | −0.0081 (3) | 0.0381 (11) | |
H4 | −0.3053 | 0.3014 | −0.0542 | 0.046* | |
C5 | −0.1915 (6) | 0.3817 (4) | 0.0882 (3) | 0.0357 (10) | |
C6 | −0.0228 (6) | 0.4410 (3) | 0.1654 (3) | 0.0355 (10) | |
N2 | −0.0100 (6) | 0.3220 (3) | −0.1370 (3) | 0.0519 (11) | |
N3 | −0.3853 (6) | 0.3565 (3) | 0.1103 (3) | 0.0519 (11) | |
N1 | 0.3360 (5) | 0.5323 (3) | 0.1964 (3) | 0.0457 (10) | |
O4 | 0.1435 (5) | 0.3507 (3) | −0.1600 (2) | 0.0651 (10) | |
O5 | −0.1613 (5) | 0.2660 (4) | −0.1961 (2) | 0.0846 (13) | |
O6 | −0.5226 (5) | 0.2978 (4) | 0.0431 (3) | 0.0888 (14) | |
O7 | −0.4014 (5) | 0.3921 (3) | 0.1936 (3) | 0.0766 (12) | |
O3 | 0.4633 (5) | 0.5818 (3) | 0.1678 (3) | 0.0723 (11) | |
O2 | 0.3608 (5) | 0.5411 (3) | 0.2786 (2) | 0.0698 (11) | |
O1 | −0.0221 (4) | 0.4752 (3) | 0.2537 (2) | 0.0477 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C11 | 0.030 (3) | 0.057 (3) | 0.039 (3) | 0.006 (2) | 0.003 (2) | 0.018 (2) |
C12 | 0.036 (3) | 0.053 (3) | 0.035 (2) | 0.017 (2) | 0.011 (2) | 0.021 (2) |
C13 | 0.046 (3) | 0.056 (3) | 0.048 (3) | 0.006 (3) | 0.006 (2) | 0.022 (3) |
C14 | 0.041 (3) | 0.050 (3) | 0.044 (3) | 0.011 (2) | 0.002 (2) | 0.017 (2) |
C15 | 0.046 (4) | 0.065 (4) | 0.096 (5) | 0.007 (3) | −0.003 (3) | 0.038 (3) |
C16 | 0.059 (4) | 0.068 (5) | 0.157 (8) | −0.012 (4) | −0.043 (5) | 0.062 (5) |
C17 | 0.140 (8) | 0.059 (4) | 0.093 (6) | −0.008 (5) | −0.056 (6) | 0.032 (4) |
C18 | 0.145 (7) | 0.071 (4) | 0.057 (4) | 0.033 (5) | 0.007 (5) | 0.017 (3) |
C19 | 0.070 (4) | 0.066 (4) | 0.047 (3) | 0.024 (3) | 0.003 (3) | 0.014 (3) |
N11 | 0.035 (2) | 0.058 (2) | 0.038 (2) | 0.0190 (19) | 0.0124 (17) | 0.0241 (19) |
O1A | 0.0347 (17) | 0.069 (2) | 0.0337 (18) | 0.0146 (16) | 0.0057 (14) | 0.0239 (16) |
O1B | 0.075 (3) | 0.105 (3) | 0.053 (2) | 0.060 (2) | 0.0075 (19) | 0.022 (2) |
C21 | 0.034 (3) | 0.048 (3) | 0.036 (2) | 0.019 (2) | 0.017 (2) | 0.017 (2) |
C22 | 0.029 (2) | 0.046 (3) | 0.032 (2) | 0.010 (2) | 0.0116 (19) | 0.014 (2) |
C23 | 0.048 (3) | 0.048 (3) | 0.046 (3) | 0.013 (2) | 0.006 (2) | 0.019 (2) |
C24 | 0.050 (3) | 0.041 (3) | 0.065 (3) | 0.016 (3) | 0.008 (3) | 0.023 (3) |
C25 | 0.054 (4) | 0.087 (5) | 0.159 (7) | 0.017 (4) | 0.009 (4) | 0.073 (5) |
C26 | 0.071 (6) | 0.128 (7) | 0.260 (13) | 0.029 (5) | −0.026 (7) | 0.103 (8) |
C27 | 0.142 (10) | 0.118 (8) | 0.189 (11) | 0.011 (7) | −0.083 (9) | 0.087 (7) |
C28 | 0.173 (9) | 0.081 (5) | 0.096 (6) | 0.034 (6) | −0.015 (6) | 0.050 (4) |
C29 | 0.099 (5) | 0.063 (4) | 0.065 (4) | 0.034 (4) | 0.018 (3) | 0.034 (3) |
N22 | 0.036 (2) | 0.050 (2) | 0.036 (2) | 0.0181 (19) | 0.0154 (17) | 0.0190 (18) |
O2A | 0.044 (2) | 0.067 (2) | 0.058 (2) | 0.0255 (17) | 0.0257 (16) | 0.0406 (18) |
O2B | 0.034 (2) | 0.077 (3) | 0.086 (3) | 0.0129 (19) | 0.0013 (18) | 0.046 (2) |
C1 | 0.029 (2) | 0.046 (3) | 0.037 (2) | 0.013 (2) | 0.008 (2) | 0.022 (2) |
C2 | 0.034 (3) | 0.052 (3) | 0.046 (3) | 0.019 (2) | 0.019 (2) | 0.031 (2) |
C3 | 0.035 (3) | 0.050 (3) | 0.031 (2) | 0.020 (2) | 0.011 (2) | 0.019 (2) |
C4 | 0.027 (2) | 0.047 (3) | 0.043 (3) | 0.014 (2) | 0.008 (2) | 0.020 (2) |
C5 | 0.026 (2) | 0.051 (3) | 0.040 (3) | 0.017 (2) | 0.016 (2) | 0.024 (2) |
C6 | 0.036 (3) | 0.049 (3) | 0.038 (3) | 0.025 (2) | 0.017 (2) | 0.026 (2) |
N2 | 0.051 (3) | 0.066 (3) | 0.036 (2) | 0.017 (2) | 0.014 (2) | 0.020 (2) |
N3 | 0.035 (3) | 0.066 (3) | 0.056 (3) | 0.020 (2) | 0.021 (2) | 0.024 (2) |
N1 | 0.027 (2) | 0.068 (3) | 0.049 (2) | 0.018 (2) | 0.0122 (18) | 0.030 (2) |
O4 | 0.053 (2) | 0.093 (3) | 0.051 (2) | 0.016 (2) | 0.0305 (18) | 0.0339 (19) |
O5 | 0.048 (2) | 0.134 (4) | 0.039 (2) | 0.014 (2) | 0.0097 (18) | 0.014 (2) |
O6 | 0.027 (2) | 0.143 (4) | 0.070 (3) | 0.012 (2) | 0.011 (2) | 0.030 (3) |
O7 | 0.044 (2) | 0.102 (3) | 0.061 (2) | 0.011 (2) | 0.0336 (18) | 0.016 (2) |
O3 | 0.033 (2) | 0.110 (3) | 0.072 (2) | 0.000 (2) | 0.0127 (18) | 0.052 (2) |
O2 | 0.039 (2) | 0.123 (3) | 0.044 (2) | 0.012 (2) | 0.0046 (16) | 0.042 (2) |
O1 | 0.0377 (18) | 0.079 (2) | 0.0388 (19) | 0.0296 (17) | 0.0180 (14) | 0.0282 (17) |
C11—O1A | 1.227 (5) | C24—C25 | 1.389 (8) |
C11—O1B | 1.269 (6) | C25—C26 | 1.376 (10) |
C11—C12 | 1.525 (6) | C25—H25 | 0.9300 |
C12—N11 | 1.485 (5) | C26—C27 | 1.360 (14) |
C12—C13 | 1.531 (6) | C26—H26 | 0.9300 |
C12—H12 | 0.9800 | C27—C28 | 1.350 (13) |
C13—C14 | 1.492 (6) | C27—H27 | 0.9300 |
C13—H13A | 0.9700 | C28—C29 | 1.394 (9) |
C13—H13B | 0.9700 | C28—H28 | 0.9300 |
C14—C19 | 1.379 (7) | C29—H29 | 0.9300 |
C14—C15 | 1.386 (7) | N22—H22A | 0.8900 |
C15—C16 | 1.389 (9) | N22—H22B | 0.8900 |
C15—H15 | 0.9300 | N22—H22C | 0.8900 |
C16—C17 | 1.387 (11) | O2B—H2B | 0.8200 |
C16—H16 | 0.9300 | C1—C2 | 1.366 (5) |
C17—C18 | 1.335 (11) | C1—N1 | 1.449 (5) |
C17—H17 | 0.9300 | C1—C6 | 1.461 (5) |
C18—C19 | 1.378 (8) | C2—C3 | 1.370 (6) |
C18—H18 | 0.9300 | C2—H2 | 0.9300 |
C19—H19 | 0.9300 | C3—C4 | 1.396 (6) |
N11—H11A | 0.8900 | C3—N2 | 1.435 (5) |
N11—H11B | 0.8900 | C4—C5 | 1.365 (5) |
N11—H11C | 0.8900 | C4—H4 | 0.9300 |
C21—O2A | 1.211 (5) | C5—C6 | 1.437 (6) |
C21—O2B | 1.298 (5) | C5—N3 | 1.474 (5) |
C21—C22 | 1.499 (6) | C6—O1 | 1.250 (4) |
C22—N22 | 1.484 (5) | N2—O5 | 1.217 (5) |
C22—C23 | 1.526 (6) | N2—O4 | 1.221 (5) |
C22—H22 | 0.9800 | N3—O7 | 1.209 (4) |
C23—C24 | 1.488 (6) | N3—O6 | 1.214 (5) |
C23—H23A | 0.9700 | N1—O2 | 1.216 (4) |
C23—H23B | 0.9700 | N1—O3 | 1.224 (4) |
C24—C29 | 1.377 (7) | ||
O1A—C11—O1B | 126.0 (4) | H23A—C23—H23B | 107.6 |
O1A—C11—C12 | 120.9 (5) | C29—C24—C25 | 118.2 (5) |
O1B—C11—C12 | 113.1 (4) | C29—C24—C23 | 121.8 (5) |
N11—C12—C11 | 109.8 (4) | C25—C24—C23 | 120.0 (5) |
N11—C12—C13 | 111.5 (4) | C26—C25—C24 | 119.9 (8) |
C11—C12—C13 | 109.6 (4) | C26—C25—H25 | 120.0 |
N11—C12—H12 | 108.6 | C24—C25—H25 | 120.0 |
C11—C12—H12 | 108.6 | C27—C26—C25 | 120.7 (9) |
C13—C12—H12 | 108.6 | C27—C26—H26 | 119.6 |
C14—C13—C12 | 117.4 (4) | C25—C26—H26 | 119.6 |
C14—C13—H13A | 108.0 | C28—C27—C26 | 120.8 (9) |
C12—C13—H13A | 108.0 | C28—C27—H27 | 119.6 |
C14—C13—H13B | 108.0 | C26—C27—H27 | 119.6 |
C12—C13—H13B | 108.0 | C27—C28—C29 | 119.1 (9) |
H13A—C13—H13B | 107.2 | C27—C28—H28 | 120.4 |
C19—C14—C15 | 117.6 (5) | C29—C28—H28 | 120.4 |
C19—C14—C13 | 120.8 (4) | C24—C29—C28 | 121.2 (7) |
C15—C14—C13 | 121.4 (5) | C24—C29—H29 | 119.4 |
C14—C15—C16 | 120.4 (6) | C28—C29—H29 | 119.4 |
C14—C15—H15 | 119.8 | C22—N22—H22A | 109.5 |
C16—C15—H15 | 119.8 | C22—N22—H22B | 109.5 |
C17—C16—C15 | 119.6 (7) | H22A—N22—H22B | 109.5 |
C17—C16—H16 | 120.2 | C22—N22—H22C | 109.5 |
C15—C16—H16 | 120.2 | H22A—N22—H22C | 109.5 |
C18—C17—C16 | 120.5 (7) | H22B—N22—H22C | 109.5 |
C18—C17—H17 | 119.7 | C21—O2B—H2B | 109.5 |
C16—C17—H17 | 119.7 | C2—C1—N1 | 117.4 (4) |
C17—C18—C19 | 120.0 (7) | C2—C1—C6 | 123.2 (4) |
C17—C18—H18 | 120.0 | N1—C1—C6 | 119.3 (4) |
C19—C18—H18 | 120.0 | C1—C2—C3 | 120.8 (4) |
C18—C19—C14 | 121.9 (6) | C1—C2—H2 | 119.6 |
C18—C19—H19 | 119.1 | C3—C2—H2 | 119.6 |
C14—C19—H19 | 119.1 | C2—C3—C4 | 120.3 (4) |
C12—N11—H11A | 109.5 | C2—C3—N2 | 120.3 (4) |
C12—N11—H11B | 109.5 | C4—C3—N2 | 119.3 (4) |
H11A—N11—H11B | 109.5 | C5—C4—C3 | 118.7 (4) |
C12—N11—H11C | 109.5 | C5—C4—H4 | 120.6 |
H11A—N11—H11C | 109.5 | C3—C4—H4 | 120.6 |
H11B—N11—H11C | 109.5 | C4—C5—C6 | 125.4 (4) |
O2A—C21—O2B | 125.3 (4) | C4—C5—N3 | 114.7 (4) |
O2A—C21—C22 | 122.8 (4) | C6—C5—N3 | 120.0 (4) |
O2B—C21—C22 | 111.9 (4) | O1—C6—C5 | 125.9 (4) |
N22—C22—C21 | 109.1 (3) | O1—C6—C1 | 122.6 (4) |
N22—C22—C23 | 111.9 (3) | C5—C6—C1 | 111.4 (4) |
C21—C22—C23 | 111.0 (3) | O5—N2—O4 | 122.6 (4) |
N22—C22—H22 | 108.3 | O5—N2—C3 | 118.9 (4) |
C21—C22—H22 | 108.3 | O4—N2—C3 | 118.4 (4) |
C23—C22—H22 | 108.3 | O7—N3—O6 | 122.7 (4) |
C24—C23—C22 | 114.3 (4) | O7—N3—C5 | 119.4 (4) |
C24—C23—H23A | 108.7 | O6—N3—C5 | 117.8 (4) |
C22—C23—H23A | 108.7 | O2—N1—O3 | 121.5 (4) |
C24—C23—H23B | 108.7 | O2—N1—C1 | 120.8 (4) |
C22—C23—H23B | 108.7 | O3—N1—C1 | 117.7 (4) |
O1A—C11—C12—N11 | 15.2 (6) | C23—C24—C29—C28 | 179.8 (5) |
O1B—C11—C12—N11 | −166.0 (4) | C27—C28—C29—C24 | −0.1 (11) |
O1A—C11—C12—C13 | −107.6 (5) | N1—C1—C2—C3 | −177.0 (4) |
O1B—C11—C12—C13 | 71.2 (5) | C6—C1—C2—C3 | 0.2 (6) |
N11—C12—C13—C14 | 80.3 (5) | C1—C2—C3—C4 | 3.1 (6) |
C11—C12—C13—C14 | −157.9 (4) | C1—C2—C3—N2 | 179.7 (4) |
C12—C13—C14—C19 | 59.9 (6) | C2—C3—C4—C5 | −2.1 (6) |
C12—C13—C14—C15 | −124.4 (5) | N2—C3—C4—C5 | −178.7 (4) |
C19—C14—C15—C16 | 1.9 (8) | C3—C4—C5—C6 | −2.4 (7) |
C13—C14—C15—C16 | −173.9 (5) | C3—C4—C5—N3 | 179.7 (4) |
C14—C15—C16—C17 | −1.1 (9) | C4—C5—C6—O1 | −177.8 (4) |
C15—C16—C17—C18 | −0.1 (11) | N3—C5—C6—O1 | 0.0 (6) |
C16—C17—C18—C19 | 0.3 (11) | C4—C5—C6—C1 | 5.1 (6) |
C17—C18—C19—C14 | 0.5 (9) | N3—C5—C6—C1 | −177.1 (4) |
C15—C14—C19—C18 | −1.6 (8) | C2—C1—C6—O1 | 178.8 (4) |
C13—C14—C19—C18 | 174.2 (5) | N1—C1—C6—O1 | −4.1 (6) |
O2A—C21—C22—N22 | 11.3 (6) | C2—C1—C6—C5 | −4.0 (6) |
O2B—C21—C22—N22 | −169.1 (3) | N1—C1—C6—C5 | 173.1 (4) |
O2A—C21—C22—C23 | −112.5 (5) | C2—C3—N2—O5 | 179.2 (4) |
O2B—C21—C22—C23 | 67.2 (5) | C4—C3—N2—O5 | −4.3 (6) |
N22—C22—C23—C24 | 59.8 (5) | C2—C3—N2—O4 | −4.4 (6) |
C21—C22—C23—C24 | −178.1 (4) | C4—C3—N2—O4 | 172.2 (4) |
C22—C23—C24—C29 | 69.7 (6) | C4—C5—N3—O7 | −177.4 (4) |
C22—C23—C24—C25 | −111.1 (6) | C6—C5—N3—O7 | 4.6 (6) |
C29—C24—C25—C26 | 0.1 (10) | C4—C5—N3—O6 | 4.4 (6) |
C23—C24—C25—C26 | −179.1 (7) | C6—C5—N3—O6 | −173.6 (4) |
C24—C25—C26—C27 | −1.5 (14) | C2—C1—N1—O2 | −156.9 (4) |
C25—C26—C27—C28 | 2.1 (17) | C6—C1—N1—O2 | 25.9 (6) |
C26—C27—C28—C29 | −1.3 (15) | C2—C1—N1—O3 | 23.1 (6) |
C25—C24—C29—C28 | 0.6 (8) | C6—C1—N1—O3 | −154.2 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11A···O1 | 0.89 | 2.01 | 2.875 (4) | 165 |
N11—H11B···O1Ai | 0.89 | 2.07 | 2.923 (4) | 159 |
N11—H11C···O2A | 0.89 | 2.01 | 2.888 (4) | 168 |
N22—H22A···O2i | 0.89 | 2.60 | 3.037 (4) | 111 |
N22—H22A···O3i | 0.89 | 2.48 | 3.266 (5) | 148 |
N22—H22A···O4ii | 0.89 | 2.57 | 3.061 (4) | 116 |
N22—H22C···O1A | 0.89 | 2.00 | 2.883 (4) | 174 |
N22—H22B···O1iii | 0.89 | 1.94 | 2.778 (5) | 156 |
N22—H22B···O7iii | 0.89 | 2.40 | 3.036 (5) | 129 |
O2B—H2B···O1Biv | 0.82 | 1.67 | 2.473 (5) | 167 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y, z+1; (iii) −x, −y+1, −z+1; (iv) x−1, y, z. |
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