Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807007015/cf2086sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807007015/cf2086Isup2.hkl |
CCDC reference: 640294
Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2; data reduction: SAINT-Plus (Bruker, 2005); program(s) used to solve structure: SHELXTL (Bruker 2001); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXTL.
C12H13N3O2·H2O | F(000) = 1056 |
Mr = 249.27 | Dx = 1.315 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 9034 reflections |
a = 22.332 (2) Å | θ = 2.9–30.1° |
b = 4.7356 (5) Å | µ = 0.10 mm−1 |
c = 24.651 (3) Å | T = 100 K |
β = 104.929 (6)° | Needle, colourless |
V = 2519.0 (5) Å3 | 0.40 × 0.16 × 0.08 mm |
Z = 8 |
Bruker X8 APEXII diffractometer | 4387 independent reflections |
Radiation source: fine-focus sealed tube | 3182 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
ω and φ scans | θmax = 25.4°, θmin = 3.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1998) | h = −26→26 |
Tmin = 0.927, Tmax = 0.985 | k = −5→5 |
27588 measured reflections | l = −28→27 |
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)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.176 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0711P)2 + 4.6214P] where P = (Fo2 + 2Fc2)/3 |
4387 reflections | (Δ/σ)max = 0.003 |
345 parameters | Δρmax = 0.95 e Å−3 |
13 restraints | Δρmin = −0.77 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 | Occ. (<1) | |
N1 | 0.14974 (10) | −0.1946 (5) | 0.09385 (10) | 0.0260 (6) | |
N2 | 0.14440 (9) | 0.2986 (5) | 0.20435 (9) | 0.0202 (5) | |
N3 | 0.09557 (10) | 0.4700 (5) | 0.20315 (9) | 0.0216 (5) | |
O1 | 0.05648 (9) | 0.2543 (4) | 0.29203 (8) | 0.0305 (5) | |
O2 | 0.10854 (8) | 0.5945 (4) | 0.34809 (8) | 0.0261 (5) | |
C1 | 0.18800 (13) | −0.3854 (7) | 0.08040 (13) | 0.0323 (7) | |
H1 | 0.1741 | −0.4824 | 0.0457 | 0.039* | |
C2 | 0.24594 (13) | −0.4496 (6) | 0.11357 (13) | 0.0304 (7) | |
H2 | 0.2713 | −0.5860 | 0.1020 | 0.037* | |
C3 | 0.26606 (12) | −0.3103 (6) | 0.16403 (12) | 0.0256 (7) | |
H3 | 0.3057 | −0.3498 | 0.1882 | 0.031* | |
C4 | 0.22787 (11) | −0.1124 (6) | 0.17904 (11) | 0.0217 (6) | |
H4 | 0.2410 | −0.0135 | 0.2136 | 0.026* | |
C5 | 0.17003 (11) | −0.0597 (6) | 0.14304 (11) | 0.0192 (6) | |
C6 | 0.12735 (11) | 0.1496 (6) | 0.15679 (11) | 0.0198 (6) | |
C7 | 0.06734 (12) | 0.2240 (6) | 0.12577 (12) | 0.0267 (6) | |
H7 | 0.0447 | 0.1492 | 0.0907 | 0.032* | |
C8 | 0.04862 (12) | 0.4279 (6) | 0.15721 (12) | 0.0272 (7) | |
H8 | 0.0097 | 0.5220 | 0.1483 | 0.033* | |
C9 | 0.09717 (12) | 0.6474 (6) | 0.25111 (11) | 0.0226 (6) | |
H9A | 0.0656 | 0.7982 | 0.2404 | 0.027* | |
H9B | 0.1384 | 0.7379 | 0.2638 | 0.027* | |
C10 | 0.08445 (11) | 0.4738 (6) | 0.29833 (11) | 0.0221 (6) | |
C11 | 0.09967 (14) | 0.4351 (7) | 0.39598 (12) | 0.0317 (7) | |
H11A | 0.1185 | 0.2454 | 0.3969 | 0.038* | |
H11B | 0.0549 | 0.4116 | 0.3930 | 0.038* | |
C12 | 0.1295 (2) | 0.5929 (11) | 0.44772 (15) | 0.0821 (17) | |
H12A | 0.1744 | 0.5990 | 0.4522 | 0.123* | |
H12B | 0.1208 | 0.4984 | 0.4802 | 0.123* | |
H12C | 0.1131 | 0.7858 | 0.4450 | 0.123* | |
N4 | 0.13995 (10) | 0.7214 (5) | 0.59836 (10) | 0.0244 (5) | |
N5 | 0.14357 (9) | 0.2208 (5) | 0.70981 (9) | 0.0199 (5) | |
N6 | 0.09557 (10) | 0.0492 (4) | 0.71125 (9) | 0.0205 (5) | |
O3 | 0.05836 (10) | 0.2304 (5) | 0.80469 (10) | 0.0387 (6) | |
O4 | 0.11124 (10) | −0.1265 (6) | 0.85499 (9) | 0.0473 (7) | |
C13 | 0.17597 (13) | 0.9154 (6) | 0.58258 (12) | 0.0277 (7) | |
H13 | 0.1590 | 1.0183 | 0.5491 | 0.033* | |
C14 | 0.23591 (13) | 0.9747 (6) | 0.61188 (12) | 0.0266 (6) | |
H14 | 0.2599 | 1.1112 | 0.5986 | 0.032* | |
C15 | 0.26003 (12) | 0.8294 (6) | 0.66121 (12) | 0.0246 (6) | |
H15 | 0.3011 | 0.8659 | 0.6828 | 0.030* | |
C16 | 0.22401 (11) | 0.6307 (6) | 0.67883 (12) | 0.0218 (6) | |
H16 | 0.2399 | 0.5289 | 0.7127 | 0.026* | |
C17 | 0.16401 (11) | 0.5816 (5) | 0.64625 (11) | 0.0191 (6) | |
C18 | 0.12330 (11) | 0.3721 (5) | 0.66278 (11) | 0.0187 (6) | |
C19 | 0.06234 (12) | 0.2962 (6) | 0.63481 (12) | 0.0261 (6) | |
H19 | 0.0377 | 0.3711 | 0.6006 | 0.031* | |
C20 | 0.04619 (12) | 0.0914 (6) | 0.66742 (12) | 0.0254 (6) | |
H20 | 0.0074 | −0.0032 | 0.6605 | 0.031* | |
C21 | 0.10115 (13) | −0.1367 (6) | 0.75851 (11) | 0.0242 (6) | |
H21A | 0.1437 | −0.2143 | 0.7698 | 0.029* | |
H21B | 0.0720 | −0.2967 | 0.7474 | 0.029* | |
C22 | 0.08733 (12) | 0.0156 (6) | 0.80798 (13) | 0.0274 (7) | |
C23 | 0.09520 (17) | −0.0295 (14) | 0.90468 (15) | 0.103 (2) | |
H23A | 0.0731 | −0.1814 | 0.9192 | 0.123* | |
H23B | 0.0670 | 0.1346 | 0.8952 | 0.123* | |
C24 | 0.1508 (2) | 0.0518 (15) | 0.94815 (18) | 0.114 (3) | |
H24A | 0.1852 | −0.0729 | 0.9463 | 0.171* | |
H24B | 0.1425 | 0.0352 | 0.9852 | 0.171* | |
H24C | 0.1617 | 0.2475 | 0.9420 | 0.171* | |
O1W | 0.03239 (11) | 0.7511 (5) | 0.01011 (10) | 0.0507 (7) | |
H1A | 0.0699 (9) | 0.761 (7) | 0.0427 (8) | 0.076* | |
H1B | −0.0006 (11) | 0.626 (8) | 0.0178 (15) | 0.076* | 0.50 |
H1C | 0.0162 (15) | 0.942 (3) | −0.0035 (17) | 0.076* | 0.50 |
O2W | 0.01234 (11) | 0.7517 (5) | 0.52880 (10) | 0.0514 (7) | |
H2A | 0.0571 (4) | 0.768 (7) | 0.5492 (13) | 0.077* | |
H2B | −0.0065 (15) | 0.939 (3) | 0.515 (2) | 0.077* | 0.50 |
H2C | 0.0049 (16) | 0.607 (8) | 0.4983 (15) | 0.077* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0221 (12) | 0.0280 (13) | 0.0276 (14) | 0.0040 (10) | 0.0061 (11) | −0.0044 (10) |
N2 | 0.0159 (11) | 0.0224 (12) | 0.0233 (13) | 0.0005 (9) | 0.0070 (10) | −0.0008 (9) |
N3 | 0.0173 (11) | 0.0238 (12) | 0.0242 (13) | 0.0013 (9) | 0.0061 (10) | −0.0037 (10) |
O1 | 0.0319 (11) | 0.0267 (11) | 0.0377 (12) | −0.0087 (9) | 0.0177 (10) | −0.0071 (9) |
O2 | 0.0273 (10) | 0.0307 (11) | 0.0223 (11) | −0.0062 (8) | 0.0098 (9) | −0.0017 (8) |
C1 | 0.0287 (16) | 0.0364 (18) | 0.0320 (18) | 0.0053 (13) | 0.0081 (14) | −0.0095 (14) |
C2 | 0.0247 (15) | 0.0297 (17) | 0.0405 (18) | 0.0066 (12) | 0.0149 (14) | −0.0038 (13) |
C3 | 0.0148 (13) | 0.0277 (16) | 0.0348 (17) | 0.0015 (11) | 0.0072 (12) | 0.0056 (12) |
C4 | 0.0183 (13) | 0.0232 (14) | 0.0235 (15) | −0.0016 (11) | 0.0050 (12) | −0.0008 (11) |
C5 | 0.0154 (13) | 0.0229 (14) | 0.0206 (14) | 0.0000 (10) | 0.0069 (11) | 0.0005 (11) |
C6 | 0.0174 (13) | 0.0220 (14) | 0.0199 (14) | −0.0002 (10) | 0.0049 (11) | −0.0006 (11) |
C7 | 0.0194 (14) | 0.0346 (17) | 0.0242 (15) | 0.0053 (12) | 0.0021 (12) | −0.0057 (12) |
C8 | 0.0188 (14) | 0.0319 (16) | 0.0298 (16) | 0.0072 (11) | 0.0043 (13) | −0.0030 (13) |
C9 | 0.0244 (14) | 0.0194 (14) | 0.0261 (15) | −0.0017 (11) | 0.0104 (12) | −0.0040 (11) |
C10 | 0.0163 (13) | 0.0242 (15) | 0.0285 (16) | 0.0014 (11) | 0.0107 (12) | −0.0041 (12) |
C11 | 0.0327 (16) | 0.0353 (18) | 0.0312 (17) | −0.0044 (13) | 0.0158 (14) | 0.0024 (13) |
C12 | 0.124 (4) | 0.094 (4) | 0.028 (2) | −0.069 (3) | 0.020 (2) | −0.006 (2) |
N4 | 0.0244 (12) | 0.0214 (12) | 0.0264 (13) | −0.0028 (9) | 0.0049 (10) | −0.0017 (10) |
N5 | 0.0166 (11) | 0.0182 (11) | 0.0266 (13) | −0.0004 (9) | 0.0087 (10) | −0.0016 (9) |
N6 | 0.0186 (11) | 0.0170 (12) | 0.0272 (13) | 0.0004 (9) | 0.0080 (10) | −0.0007 (9) |
O3 | 0.0345 (12) | 0.0357 (13) | 0.0519 (14) | 0.0062 (10) | 0.0221 (11) | −0.0107 (11) |
O4 | 0.0374 (13) | 0.0805 (19) | 0.0242 (12) | 0.0218 (12) | 0.0086 (10) | −0.0043 (12) |
C13 | 0.0355 (16) | 0.0238 (15) | 0.0236 (15) | −0.0034 (12) | 0.0071 (13) | −0.0008 (12) |
C14 | 0.0289 (15) | 0.0217 (15) | 0.0333 (17) | −0.0066 (11) | 0.0156 (13) | −0.0043 (12) |
C15 | 0.0182 (13) | 0.0219 (15) | 0.0343 (17) | −0.0017 (11) | 0.0079 (12) | −0.0070 (12) |
C16 | 0.0171 (13) | 0.0216 (14) | 0.0263 (16) | 0.0028 (10) | 0.0046 (12) | −0.0031 (11) |
C17 | 0.0192 (13) | 0.0166 (13) | 0.0224 (15) | 0.0010 (10) | 0.0071 (12) | −0.0050 (11) |
C18 | 0.0168 (13) | 0.0158 (13) | 0.0240 (15) | 0.0014 (10) | 0.0063 (11) | −0.0030 (11) |
C19 | 0.0197 (14) | 0.0254 (15) | 0.0308 (16) | −0.0021 (11) | 0.0025 (12) | 0.0016 (12) |
C20 | 0.0159 (13) | 0.0259 (15) | 0.0326 (17) | −0.0031 (11) | 0.0029 (13) | −0.0012 (12) |
C21 | 0.0259 (14) | 0.0193 (14) | 0.0299 (16) | 0.0003 (11) | 0.0116 (13) | −0.0001 (11) |
C22 | 0.0194 (14) | 0.0311 (17) | 0.0342 (17) | −0.0028 (12) | 0.0116 (13) | −0.0065 (13) |
C23 | 0.071 (3) | 0.207 (7) | 0.029 (2) | 0.065 (4) | 0.010 (2) | −0.026 (3) |
C24 | 0.104 (4) | 0.189 (7) | 0.069 (3) | −0.085 (4) | 0.058 (3) | −0.075 (4) |
O1W | 0.0407 (13) | 0.0485 (15) | 0.0482 (15) | 0.0002 (11) | −0.0149 (12) | −0.0008 (12) |
O2W | 0.0410 (14) | 0.0463 (15) | 0.0530 (16) | −0.0080 (11) | −0.0132 (12) | 0.0070 (12) |
N1—C5 | 1.342 (3) | N5—N6 | 1.353 (3) |
N1—C1 | 1.343 (3) | N6—C20 | 1.345 (3) |
N2—C6 | 1.337 (3) | N6—C21 | 1.440 (3) |
N2—N3 | 1.354 (3) | O3—C22 | 1.197 (3) |
N3—C8 | 1.345 (4) | O4—C22 | 1.327 (4) |
N3—C9 | 1.443 (3) | O4—C23 | 1.437 (4) |
O1—C10 | 1.202 (3) | C13—C14 | 1.376 (4) |
O2—C10 | 1.334 (3) | C13—H13 | 0.950 |
O2—C11 | 1.457 (3) | C14—C15 | 1.380 (4) |
C1—C2 | 1.375 (4) | C14—H14 | 0.950 |
C1—H1 | 0.950 | C15—C16 | 1.379 (4) |
C2—C3 | 1.377 (4) | C15—H15 | 0.950 |
C2—H2 | 0.950 | C16—C17 | 1.393 (4) |
C3—C4 | 1.380 (4) | C16—H16 | 0.950 |
C3—H3 | 0.950 | C17—C18 | 1.472 (4) |
C4—C5 | 1.388 (4) | C18—C19 | 1.405 (4) |
C4—H4 | 0.950 | C19—C20 | 1.366 (4) |
C5—C6 | 1.474 (3) | C19—H19 | 0.950 |
C6—C7 | 1.406 (4) | C20—H20 | 0.950 |
C7—C8 | 1.369 (4) | C21—C22 | 1.515 (4) |
C7—H7 | 0.950 | C21—H21A | 0.990 |
C8—H8 | 0.950 | C21—H21B | 0.990 |
C9—C10 | 1.511 (4) | C23—C24 | 1.467 (6) |
C9—H9A | 0.990 | C23—H23A | 0.990 |
C9—H9B | 0.990 | C23—H23B | 0.990 |
C11—C12 | 1.481 (5) | C24—H24A | 0.980 |
C11—H11A | 0.990 | C24—H24B | 0.980 |
C11—H11B | 0.990 | C24—H24C | 0.980 |
C12—H12A | 0.980 | O1W—H1A | 1.00 (1) |
C12—H12B | 0.980 | O1W—H1B | 1.00 (1) |
C12—H12C | 0.980 | O1W—H1C | 1.00 (1) |
N4—C17 | 1.339 (3) | O2W—H2A | 1.00 (1) |
N4—C13 | 1.343 (3) | O2W—H2B | 1.00 (1) |
N5—C18 | 1.339 (3) | O2W—H2C | 1.00 (1) |
C5—N1—C1 | 117.1 (2) | C20—N6—C21 | 128.5 (2) |
C6—N2—N3 | 104.6 (2) | N5—N6—C21 | 119.0 (2) |
C8—N3—N2 | 112.2 (2) | C22—O4—C23 | 116.7 (3) |
C8—N3—C9 | 128.7 (2) | N4—C13—C14 | 124.2 (3) |
N2—N3—C9 | 118.8 (2) | N4—C13—H13 | 117.9 |
C10—O2—C11 | 114.6 (2) | C14—C13—H13 | 117.9 |
N1—C1—C2 | 124.3 (3) | C13—C14—C15 | 117.8 (3) |
N1—C1—H1 | 117.9 | C13—C14—H14 | 121.1 |
C2—C1—H1 | 117.9 | C15—C14—H14 | 121.1 |
C1—C2—C3 | 118.0 (3) | C16—C15—C14 | 119.4 (3) |
C1—C2—H2 | 121.0 | C16—C15—H15 | 120.3 |
C3—C2—H2 | 121.0 | C14—C15—H15 | 120.3 |
C2—C3—C4 | 119.2 (3) | C15—C16—C17 | 119.0 (3) |
C2—C3—H3 | 120.4 | C15—C16—H16 | 120.5 |
C4—C3—H3 | 120.4 | C17—C16—H16 | 120.5 |
C3—C4—C5 | 119.2 (3) | N4—C17—C16 | 122.2 (2) |
C3—C4—H4 | 120.4 | N4—C17—C18 | 116.2 (2) |
C5—C4—H4 | 120.4 | C16—C17—C18 | 121.6 (2) |
N1—C5—C4 | 122.3 (2) | N5—C18—C19 | 110.9 (2) |
N1—C5—C6 | 116.1 (2) | N5—C18—C17 | 120.3 (2) |
C4—C5—C6 | 121.6 (2) | C19—C18—C17 | 128.8 (2) |
N2—C6—C7 | 111.2 (2) | C20—C19—C18 | 105.2 (2) |
N2—C6—C5 | 120.1 (2) | C20—C19—H19 | 127.4 |
C7—C6—C5 | 128.7 (2) | C18—C19—H19 | 127.4 |
C8—C7—C6 | 104.8 (2) | N6—C20—C19 | 107.0 (2) |
C8—C7—H7 | 127.6 | N6—C20—H20 | 126.5 |
C6—C7—H7 | 127.6 | C19—C20—H20 | 126.5 |
N3—C8—C7 | 107.2 (2) | N6—C21—C22 | 111.5 (2) |
N3—C8—H8 | 126.4 | N6—C21—H21A | 109.3 |
C7—C8—H8 | 126.4 | C22—C21—H21A | 109.3 |
N3—C9—C10 | 110.2 (2) | N6—C21—H21B | 109.3 |
N3—C9—H9A | 109.6 | C22—C21—H21B | 109.3 |
C10—C9—H9A | 109.6 | H21A—C21—H21B | 108.0 |
N3—C9—H9B | 109.6 | O3—C22—O4 | 125.4 (3) |
C10—C9—H9B | 109.6 | O3—C22—C21 | 124.6 (3) |
H9A—C9—H9B | 108.1 | O4—C22—C21 | 110.0 (2) |
O1—C10—O2 | 124.2 (3) | O4—C23—C24 | 110.9 (3) |
O1—C10—C9 | 124.4 (3) | O4—C23—H23A | 109.5 |
O2—C10—C9 | 111.3 (2) | C24—C23—H23A | 109.5 |
O2—C11—C12 | 108.1 (3) | O4—C23—H23B | 109.5 |
O2—C11—H11A | 110.1 | C24—C23—H23B | 109.5 |
C12—C11—H11A | 110.1 | H23A—C23—H23B | 108.0 |
O2—C11—H11B | 110.1 | C23—C24—H24A | 109.5 |
C12—C11—H11B | 110.1 | C23—C24—H24B | 109.5 |
H11A—C11—H11B | 108.4 | H24A—C24—H24B | 109.5 |
C11—C12—H12A | 109.5 | C23—C24—H24C | 109.5 |
C11—C12—H12B | 109.5 | H24A—C24—H24C | 109.5 |
H12A—C12—H12B | 109.5 | H24B—C24—H24C | 109.5 |
C11—C12—H12C | 109.5 | H1A—O1W—H1B | 112.39 (17) |
H12A—C12—H12C | 109.5 | H1A—O1W—H1C | 112.40 (17) |
H12B—C12—H12C | 109.5 | H1B—O1W—H1C | 112.39 (17) |
C17—N4—C13 | 117.3 (2) | H2A—O2W—H2B | 112.39 (17) |
C18—N5—N6 | 104.5 (2) | H2A—O2W—H2C | 112.38 (17) |
C20—N6—N5 | 112.4 (2) | H2B—O2W—H2C | 112.38 (17) |
C6—N2—N3—C8 | 1.3 (3) | C18—N5—N6—C20 | −0.9 (3) |
C6—N2—N3—C9 | 175.6 (2) | C18—N5—N6—C21 | −177.5 (2) |
C5—N1—C1—C2 | 0.0 (4) | C17—N4—C13—C14 | 1.2 (4) |
N1—C1—C2—C3 | 0.3 (5) | N4—C13—C14—C15 | −1.4 (4) |
C1—C2—C3—C4 | −0.4 (4) | C13—C14—C15—C16 | 0.7 (4) |
C2—C3—C4—C5 | 0.3 (4) | C14—C15—C16—C17 | 0.0 (4) |
C1—N1—C5—C4 | −0.1 (4) | C13—N4—C17—C16 | −0.4 (4) |
C1—N1—C5—C6 | 179.7 (2) | C13—N4—C17—C18 | 179.5 (2) |
C3—C4—C5—N1 | 0.0 (4) | C15—C16—C17—N4 | −0.2 (4) |
C3—C4—C5—C6 | −179.8 (2) | C15—C16—C17—C18 | 179.9 (2) |
N3—N2—C6—C7 | −0.8 (3) | N6—N5—C18—C19 | 0.3 (3) |
N3—N2—C6—C5 | 179.1 (2) | N6—N5—C18—C17 | −178.8 (2) |
N1—C5—C6—N2 | −178.4 (2) | N4—C17—C18—N5 | 179.5 (2) |
C4—C5—C6—N2 | 1.4 (4) | C16—C17—C18—N5 | −0.6 (4) |
N1—C5—C6—C7 | 1.4 (4) | N4—C17—C18—C19 | 0.6 (4) |
C4—C5—C6—C7 | −178.7 (3) | C16—C17—C18—C19 | −179.6 (3) |
N2—C6—C7—C8 | 0.0 (3) | N5—C18—C19—C20 | 0.4 (3) |
C5—C6—C7—C8 | −179.9 (3) | C17—C18—C19—C20 | 179.4 (3) |
N2—N3—C8—C7 | −1.3 (3) | N5—N6—C20—C19 | 1.2 (3) |
C9—N3—C8—C7 | −174.9 (3) | C21—N6—C20—C19 | 177.3 (2) |
C6—C7—C8—N3 | 0.8 (3) | C18—C19—C20—N6 | −0.9 (3) |
C8—N3—C9—C10 | 97.2 (3) | C20—N6—C21—C22 | −94.1 (3) |
N2—N3—C9—C10 | −76.0 (3) | N5—N6—C21—C22 | 81.8 (3) |
C11—O2—C10—O1 | 1.3 (4) | C23—O4—C22—O3 | 7.0 (5) |
C11—O2—C10—C9 | −178.4 (2) | C23—O4—C22—C21 | −172.1 (3) |
N3—C9—C10—O1 | −24.1 (4) | N6—C21—C22—O3 | 20.7 (4) |
N3—C9—C10—O2 | 155.5 (2) | N6—C21—C22—O4 | −160.2 (2) |
C10—O2—C11—C12 | 179.2 (3) | C22—O4—C23—C24 | −120.1 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1A···N1i | 1.00 (1) | 1.91 (2) | 2.900 (3) | 168 (3) |
O1W—H1B···O1Wii | 1.00 (1) | 1.98 (3) | 2.762 (5) | 133 (4) |
O1W—H1C···O1Wiii | 1.00 (1) | 1.80 (2) | 2.743 (5) | 157 (4) |
O2W—H2A···N4 | 1.00 (1) | 1.95 (2) | 2.926 (3) | 166 (3) |
O2W—H2B···O2Wiv | 1.00 (1) | 1.81 (3) | 2.729 (5) | 152 (4) |
O2W—H2C···O2Wv | 1.00 (1) | 1.83 (2) | 2.757 (5) | 153 (5) |
C8—H8···O3v | 0.95 | 2.44 | 3.219 (3) | 140 |
C9—H9A···O1i | 0.99 | 2.54 | 3.252 (3) | 129 |
C19—H19···O2W | 0.95 | 2.49 | 3.351 (4) | 151 |
C20—H20···O1vi | 0.95 | 2.38 | 3.181 (3) | 141 |
Symmetry codes: (i) x, y+1, z; (ii) −x, −y+1, −z; (iii) −x, −y+2, −z; (iv) −x, −y+2, −z+1; (v) −x, −y+1, −z+1; (vi) −x, −y, −z+1. |