| Literature DB >> 21754812 |
Manickam Buvaneswari1, Doraisamyraja Kalaivani.
Abstract
In the title mol-ecular salt, C(6)H(16)NO(+)·C(10)H(4)N(5)O(9) (-)·2H(2)O, which crystallizes as a dihydrate, O-H⋯O hydrogen bonds link the barbiturate anion, the ethanaminium cation and the water mol-ecules of crystallization. The dihedral angle between the rings in the anion is 43.71 (8)°. In the crystal, an R(2) (2)(8) ring motif hydrogen-bonding pattern is also found involving inversion-related barbiturate rings with N-H⋯O hydrogen bonds. As a result of the various hydrogen bonds an infinite two-dimensional network, propagating in (10[Formula: see text]), is formed.Entities:
Year: 2011 PMID: 21754812 PMCID: PMC3120611 DOI: 10.1107/S1600536811017363
Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN: 1600-5368
| C6H16NO+·C10H4N5O9−·2H2O | |
| Monoclinic, | Mo |
| Hall symbol: -P 2yn | Cell parameters from 5467 reflections |
| θ = 2.6–24.8° | |
| µ = 0.13 mm−1 | |
| β = 96.118 (1)° | Block, red |
| 0.30 × 0.25 × 0.20 mm | |
| Bruker Kappa APEXII CCD diffractometer | 4686 independent reflections |
| Radiation source: fine-focus sealed tube | 3492 reflections with |
| graphite | |
| ω and φ scans | θmax = 26.8°, θmin = 1.9° |
| Absorption correction: multi-scan ( | |
| 23280 measured reflections |
| Refinement on | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| Hydrogen site location: inferred from neighbouring sites | |
| H atoms treated by a mixture of independent and constrained refinement | |
| 4686 reflections | (Δ/σ)max < 0.001 |
| 338 parameters | Δρmax = 0.36 e Å−3 |
| 6 restraints | Δρmin = −0.32 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 |
| C1 | 0.7186 (2) | 0.41169 (8) | 0.30054 (14) | 0.0306 (4) | |
| C2 | 0.5959 (2) | 0.43691 (8) | 0.11393 (15) | 0.0388 (4) | |
| C3 | 0.6102 (2) | 0.51490 (7) | 0.25866 (14) | 0.0300 (4) | |
| C4 | 0.6886 (2) | 0.47250 (7) | 0.33442 (14) | 0.0292 (4) | |
| C5 | 0.73603 (19) | 0.49194 (7) | 0.44825 (13) | 0.0266 (3) | |
| C6 | 0.81044 (19) | 0.54867 (8) | 0.47588 (14) | 0.0302 (4) | |
| C7 | 0.8515 (2) | 0.56930 (8) | 0.58266 (15) | 0.0356 (4) | |
| H7 | 0.8973 | 0.6079 | 0.5960 | 0.043* | |
| C8 | 0.8230 (2) | 0.53139 (8) | 0.66853 (15) | 0.0350 (4) | |
| C9 | 0.7534 (2) | 0.47444 (8) | 0.65025 (15) | 0.0327 (4) | |
| H9 | 0.7364 | 0.4487 | 0.7092 | 0.039* | |
| C10 | 0.70989 (19) | 0.45705 (7) | 0.54204 (14) | 0.0286 (4) | |
| C11 | 0.4444 (3) | 0.22119 (12) | 0.27523 (19) | 0.0554 (6) | |
| H11A | 0.5560 | 0.2339 | 0.2822 | 0.067* | |
| H11B | 0.4334 | 0.1863 | 0.2251 | 0.067* | |
| C12 | 0.3427 (4) | 0.27264 (14) | 0.2257 (2) | 0.0765 (8) | |
| H12A | 0.2315 | 0.2631 | 0.2295 | 0.115* | |
| H12B | 0.3616 | 0.2782 | 0.1494 | 0.115* | |
| H12C | 0.3695 | 0.3098 | 0.2664 | 0.115* | |
| C13 | 0.4327 (3) | 0.25114 (9) | 0.47133 (18) | 0.0488 (5) | |
| H13A | 0.3762 | 0.2878 | 0.4436 | 0.059* | |
| H13B | 0.5466 | 0.2604 | 0.4794 | 0.059* | |
| C14 | 0.3828 (3) | 0.23605 (10) | 0.58351 (17) | 0.0475 (5) | |
| H14A | 0.4519 | 0.2039 | 0.6172 | 0.057* | |
| H14B | 0.3969 | 0.2721 | 0.6307 | 0.057* | |
| C15 | 0.4762 (3) | 0.14050 (9) | 0.42105 (19) | 0.0504 (5) | |
| H15A | 0.4378 | 0.1276 | 0.4903 | 0.060* | |
| H15B | 0.4401 | 0.1103 | 0.3648 | 0.060* | |
| C16 | 0.6552 (3) | 0.14057 (14) | 0.4358 (2) | 0.0731 (8) | |
| H16A | 0.6949 | 0.1503 | 0.3663 | 0.110* | |
| H16B | 0.6933 | 0.1007 | 0.4602 | 0.110* | |
| H16C | 0.6926 | 0.1707 | 0.4905 | 0.110* | |
| N1 | 0.6672 (2) | 0.39757 (7) | 0.19009 (13) | 0.0372 (4) | |
| N2 | 0.5695 (2) | 0.49417 (7) | 0.15108 (13) | 0.0399 (4) | |
| N3 | 0.85714 (19) | 0.59043 (7) | 0.38903 (14) | 0.0390 (4) | |
| N4 | 0.8702 (2) | 0.55069 (9) | 0.78267 (15) | 0.0504 (4) | |
| N5 | 0.62095 (18) | 0.39864 (6) | 0.53118 (12) | 0.0323 (3) | |
| N6 | 0.4013 (2) | 0.20141 (7) | 0.38774 (14) | 0.0391 (4) | |
| O1 | 0.78610 (16) | 0.37089 (6) | 0.35927 (10) | 0.0405 (3) | |
| O2 | 0.5564 (2) | 0.42190 (6) | 0.01670 (11) | 0.0583 (4) | |
| O1W | 0.42307 (17) | 0.66131 (6) | 0.15158 (11) | 0.0433 (3) | |
| O3 | 0.57236 (15) | 0.56815 (5) | 0.28132 (10) | 0.0351 (3) | |
| O2W | 0.9751 (3) | 0.27123 (10) | 0.4379 (2) | 0.1173 (10) | |
| O4 | 0.8348 (2) | 0.64511 (6) | 0.40147 (14) | 0.0615 (4) | |
| O5 | 0.92002 (16) | 0.56847 (7) | 0.31178 (12) | 0.0482 (4) | |
| O6 | 0.9235 (3) | 0.60220 (9) | 0.79794 (14) | 0.0794 (6) | |
| O7 | 0.8528 (3) | 0.51453 (9) | 0.85712 (14) | 0.0882 (7) | |
| O8 | 0.66984 (18) | 0.35673 (6) | 0.59242 (12) | 0.0486 (4) | |
| O9 | 0.50041 (15) | 0.39638 (6) | 0.46545 (11) | 0.0408 (3) | |
| O10 | 0.22086 (17) | 0.21639 (6) | 0.57806 (12) | 0.0449 (3) | |
| H10 | 0.1618 | 0.2438 | 0.5511 | 0.071 (8)* | |
| H6 | 0.294 (3) | 0.1935 (11) | 0.377 (2) | 0.063 (7)* | |
| H1A | 0.686 (3) | 0.3612 (11) | 0.1685 (19) | 0.052 (6)* | |
| H2A | 0.526 (3) | 0.5191 (10) | 0.1057 (18) | 0.044 (6)* | |
| H1W | 0.467 (3) | 0.6368 (9) | 0.2074 (13) | 0.071 (8)* | |
| H2W | 0.424 (4) | 0.6446 (11) | 0.0830 (10) | 0.091 (10)* | |
| H4W | 0.978 (5) | 0.2365 (12) | 0.393 (3) | 0.162 (18)* | |
| H3W | 0.895 (4) | 0.2983 (15) | 0.411 (3) | 0.160 (17)* |
| C1 | 0.0348 (9) | 0.0271 (8) | 0.0296 (9) | 0.0051 (7) | 0.0016 (7) | −0.0002 (7) |
| C2 | 0.0517 (11) | 0.0312 (9) | 0.0317 (9) | 0.0083 (8) | −0.0043 (8) | −0.0032 (8) |
| C3 | 0.0314 (8) | 0.0280 (8) | 0.0301 (9) | 0.0034 (7) | 0.0004 (7) | −0.0016 (7) |
| C4 | 0.0326 (9) | 0.0261 (8) | 0.0279 (8) | 0.0042 (7) | −0.0011 (7) | −0.0002 (7) |
| C5 | 0.0244 (8) | 0.0238 (8) | 0.0306 (8) | 0.0049 (6) | −0.0014 (6) | −0.0006 (6) |
| C6 | 0.0292 (8) | 0.0260 (8) | 0.0347 (9) | 0.0010 (6) | −0.0005 (7) | 0.0006 (7) |
| C7 | 0.0334 (9) | 0.0296 (9) | 0.0425 (10) | −0.0024 (7) | −0.0016 (7) | −0.0068 (8) |
| C8 | 0.0330 (9) | 0.0385 (10) | 0.0318 (9) | 0.0007 (7) | −0.0046 (7) | −0.0087 (8) |
| C9 | 0.0334 (9) | 0.0329 (9) | 0.0306 (9) | 0.0022 (7) | −0.0021 (7) | 0.0028 (7) |
| C10 | 0.0282 (8) | 0.0234 (8) | 0.0332 (9) | 0.0010 (6) | −0.0017 (6) | −0.0008 (7) |
| C11 | 0.0560 (13) | 0.0660 (15) | 0.0457 (12) | −0.0002 (11) | 0.0114 (10) | 0.0030 (11) |
| C12 | 0.0832 (19) | 0.085 (2) | 0.0612 (16) | 0.0084 (15) | 0.0074 (14) | 0.0235 (14) |
| C13 | 0.0556 (13) | 0.0366 (10) | 0.0552 (13) | −0.0108 (9) | 0.0103 (10) | −0.0117 (9) |
| C14 | 0.0560 (13) | 0.0404 (11) | 0.0445 (11) | −0.0031 (9) | −0.0013 (9) | −0.0096 (9) |
| C15 | 0.0569 (13) | 0.0376 (11) | 0.0558 (13) | 0.0069 (9) | 0.0021 (10) | −0.0051 (9) |
| C16 | 0.0578 (15) | 0.0869 (19) | 0.0718 (17) | 0.0213 (14) | −0.0061 (12) | −0.0082 (15) |
| N1 | 0.0529 (10) | 0.0254 (8) | 0.0319 (8) | 0.0097 (7) | −0.0019 (7) | −0.0048 (6) |
| N2 | 0.0599 (11) | 0.0290 (8) | 0.0278 (8) | 0.0144 (7) | −0.0094 (7) | −0.0010 (6) |
| N3 | 0.0379 (8) | 0.0326 (8) | 0.0460 (9) | −0.0053 (6) | 0.0016 (7) | 0.0030 (7) |
| N4 | 0.0570 (11) | 0.0543 (11) | 0.0378 (9) | −0.0070 (9) | −0.0040 (8) | −0.0117 (8) |
| N5 | 0.0382 (8) | 0.0256 (7) | 0.0328 (8) | −0.0008 (6) | 0.0016 (6) | 0.0000 (6) |
| N6 | 0.0398 (9) | 0.0343 (8) | 0.0432 (9) | −0.0031 (7) | 0.0049 (7) | −0.0058 (7) |
| O1 | 0.0522 (8) | 0.0303 (6) | 0.0374 (7) | 0.0153 (6) | −0.0020 (6) | 0.0024 (5) |
| O2 | 0.0989 (13) | 0.0384 (8) | 0.0327 (7) | 0.0199 (8) | −0.0160 (7) | −0.0091 (6) |
| O1W | 0.0544 (8) | 0.0367 (7) | 0.0372 (8) | 0.0126 (6) | −0.0024 (6) | 0.0005 (6) |
| O3 | 0.0445 (7) | 0.0252 (6) | 0.0340 (6) | 0.0100 (5) | −0.0029 (5) | −0.0019 (5) |
| O2W | 0.142 (2) | 0.0625 (13) | 0.128 (2) | 0.0511 (14) | −0.0737 (17) | −0.0340 (13) |
| O4 | 0.0903 (13) | 0.0250 (7) | 0.0697 (11) | −0.0070 (7) | 0.0110 (9) | 0.0037 (7) |
| O5 | 0.0441 (8) | 0.0523 (8) | 0.0502 (8) | 0.0017 (6) | 0.0148 (7) | 0.0066 (7) |
| O6 | 0.1110 (16) | 0.0719 (12) | 0.0536 (10) | −0.0391 (11) | 0.0006 (10) | −0.0260 (9) |
| O7 | 0.150 (2) | 0.0752 (13) | 0.0342 (9) | −0.0199 (13) | −0.0119 (10) | −0.0011 (9) |
| O8 | 0.0660 (10) | 0.0280 (7) | 0.0497 (8) | −0.0008 (6) | −0.0039 (7) | 0.0100 (6) |
| O9 | 0.0360 (7) | 0.0376 (7) | 0.0469 (8) | −0.0067 (5) | −0.0036 (6) | −0.0036 (6) |
| O10 | 0.0520 (8) | 0.0322 (7) | 0.0504 (8) | −0.0001 (6) | 0.0049 (6) | 0.0069 (6) |
| C1—O1 | 1.236 (2) | C13—N6 | 1.485 (2) |
| C1—N1 | 1.393 (2) | C13—C14 | 1.497 (3) |
| C1—C4 | 1.416 (2) | C13—H13A | 0.9700 |
| C2—O2 | 1.231 (2) | C13—H13B | 0.9700 |
| C2—N1 | 1.350 (2) | C14—O10 | 1.418 (3) |
| C2—N2 | 1.351 (2) | C14—H14A | 0.9700 |
| C3—O3 | 1.240 (2) | C14—H14B | 0.9700 |
| C3—N2 | 1.385 (2) | C15—C16 | 1.492 (3) |
| C3—C4 | 1.412 (2) | C15—N6 | 1.503 (3) |
| C4—C5 | 1.454 (2) | C15—H15A | 0.9700 |
| C5—C10 | 1.401 (2) | C15—H15B | 0.9700 |
| C5—C6 | 1.407 (2) | C16—H16A | 0.9600 |
| C6—C7 | 1.376 (2) | C16—H16B | 0.9600 |
| C6—N3 | 1.473 (2) | C16—H16C | 0.9600 |
| C7—C8 | 1.367 (3) | N1—H1A | 0.85 (2) |
| C7—H7 | 0.9300 | N2—H2A | 0.83 (2) |
| C8—C9 | 1.378 (2) | N3—O4 | 1.217 (2) |
| C8—N4 | 1.456 (2) | N3—O5 | 1.218 (2) |
| C9—C10 | 1.373 (2) | N4—O6 | 1.214 (2) |
| C9—H9 | 0.9300 | N4—O7 | 1.216 (2) |
| C10—N5 | 1.472 (2) | N5—O9 | 1.2177 (19) |
| C11—C12 | 1.493 (3) | N5—O8 | 1.2180 (18) |
| C11—N6 | 1.507 (3) | N6—H6 | 0.91 (3) |
| C11—H11A | 0.9700 | O1W—H1W | 0.908 (9) |
| C11—H11B | 0.9700 | O1W—H2W | 0.907 (9) |
| C12—H12A | 0.9600 | O2W—H4W | 0.933 (10) |
| C12—H12B | 0.9600 | O2W—H3W | 0.929 (10) |
| C12—H12C | 0.9600 | O10—H10 | 0.8200 |
| O1—C1—N1 | 117.90 (15) | N6—C13—H13B | 108.7 |
| O1—C1—C4 | 126.17 (15) | C14—C13—H13B | 108.7 |
| N1—C1—C4 | 115.93 (14) | H13A—C13—H13B | 107.6 |
| O2—C2—N1 | 122.52 (17) | O10—C14—C13 | 112.47 (17) |
| O2—C2—N2 | 121.69 (17) | O10—C14—H14A | 109.1 |
| N1—C2—N2 | 115.79 (16) | C13—C14—H14A | 109.1 |
| O3—C3—N2 | 117.98 (15) | O10—C14—H14B | 109.1 |
| O3—C3—C4 | 125.44 (15) | C13—C14—H14B | 109.1 |
| N2—C3—C4 | 116.56 (15) | H14A—C14—H14B | 107.8 |
| C3—C4—C1 | 120.54 (15) | C16—C15—N6 | 114.6 (2) |
| C3—C4—C5 | 119.01 (14) | C16—C15—H15A | 108.6 |
| C1—C4—C5 | 120.44 (14) | N6—C15—H15A | 108.6 |
| C10—C5—C6 | 112.77 (14) | C16—C15—H15B | 108.6 |
| C10—C5—C4 | 123.89 (15) | N6—C15—H15B | 108.6 |
| C6—C5—C4 | 123.33 (15) | H15A—C15—H15B | 107.6 |
| C7—C6—C5 | 124.70 (16) | C15—C16—H16A | 109.5 |
| C7—C6—N3 | 114.12 (15) | C15—C16—H16B | 109.5 |
| C5—C6—N3 | 121.13 (15) | H16A—C16—H16B | 109.5 |
| C8—C7—C6 | 117.98 (16) | C15—C16—H16C | 109.5 |
| C8—C7—H7 | 121.0 | H16A—C16—H16C | 109.5 |
| C6—C7—H7 | 121.0 | H16B—C16—H16C | 109.5 |
| C7—C8—C9 | 121.78 (16) | C2—N1—C1 | 125.68 (15) |
| C7—C8—N4 | 119.59 (16) | C2—N1—H1A | 117.5 (15) |
| C9—C8—N4 | 118.62 (17) | C1—N1—H1A | 116.8 (15) |
| C10—C9—C8 | 117.76 (16) | C2—N2—C3 | 125.47 (16) |
| C10—C9—H9 | 121.1 | C2—N2—H2A | 117.4 (15) |
| C8—C9—H9 | 121.1 | C3—N2—H2A | 117.1 (15) |
| C9—C10—C5 | 124.95 (15) | O4—N3—O5 | 124.29 (17) |
| C9—C10—N5 | 113.79 (15) | O4—N3—C6 | 117.36 (16) |
| C5—C10—N5 | 121.14 (14) | O5—N3—C6 | 118.30 (15) |
| C12—C11—N6 | 113.3 (2) | O6—N4—O7 | 123.81 (18) |
| C12—C11—H11A | 108.9 | O6—N4—C8 | 117.96 (19) |
| N6—C11—H11A | 108.9 | O7—N4—C8 | 118.22 (17) |
| C12—C11—H11B | 108.9 | O9—N5—O8 | 124.63 (15) |
| N6—C11—H11B | 108.9 | O9—N5—C10 | 118.02 (14) |
| H11A—C11—H11B | 107.7 | O8—N5—C10 | 117.27 (14) |
| C11—C12—H12A | 109.5 | C13—N6—C15 | 114.97 (17) |
| C11—C12—H12B | 109.5 | C13—N6—C11 | 111.34 (16) |
| H12A—C12—H12B | 109.5 | C15—N6—C11 | 111.13 (17) |
| C11—C12—H12C | 109.5 | C13—N6—H6 | 109.8 (16) |
| H12A—C12—H12C | 109.5 | C15—N6—H6 | 104.4 (16) |
| H12B—C12—H12C | 109.5 | C11—N6—H6 | 104.5 (16) |
| N6—C13—C14 | 114.21 (16) | H1W—O1W—H2W | 113.6 (14) |
| N6—C13—H13A | 108.7 | H4W—O2W—H3W | 111.6 (16) |
| C14—C13—H13A | 108.7 | C14—O10—H10 | 109.5 |
| O3—C3—C4—C1 | 176.75 (17) | N6—C13—C14—O10 | −53.0 (2) |
| N2—C3—C4—C1 | −1.6 (2) | O2—C2—N1—C1 | 178.4 (2) |
| O3—C3—C4—C5 | −2.4 (3) | N2—C2—N1—C1 | −2.0 (3) |
| N2—C3—C4—C5 | 179.24 (16) | O1—C1—N1—C2 | −178.03 (18) |
| O1—C1—C4—C3 | 179.91 (17) | C4—C1—N1—C2 | 1.6 (3) |
| N1—C1—C4—C3 | 0.3 (2) | O2—C2—N2—C3 | −179.9 (2) |
| O1—C1—C4—C5 | −1.0 (3) | N1—C2—N2—C3 | 0.4 (3) |
| N1—C1—C4—C5 | 179.45 (15) | O3—C3—N2—C2 | −177.22 (18) |
| C3—C4—C5—C10 | 134.25 (17) | C4—C3—N2—C2 | 1.3 (3) |
| C1—C4—C5—C10 | −44.9 (2) | C7—C6—N3—O4 | −42.6 (2) |
| C3—C4—C5—C6 | −44.4 (2) | C5—C6—N3—O4 | 139.73 (18) |
| C1—C4—C5—C6 | 136.50 (17) | C7—C6—N3—O5 | 135.05 (17) |
| C10—C5—C6—C7 | −1.2 (2) | C5—C6—N3—O5 | −42.6 (2) |
| C4—C5—C6—C7 | 177.56 (16) | C7—C8—N4—O6 | 5.1 (3) |
| C10—C5—C6—N3 | 176.24 (15) | C9—C8—N4—O6 | −176.2 (2) |
| C4—C5—C6—N3 | −5.0 (2) | C7—C8—N4—O7 | −175.4 (2) |
| C5—C6—C7—C8 | 2.2 (3) | C9—C8—N4—O7 | 3.3 (3) |
| N3—C6—C7—C8 | −175.40 (16) | C9—C10—N5—O9 | 133.96 (16) |
| C6—C7—C8—C9 | −0.9 (3) | C5—C10—N5—O9 | −42.3 (2) |
| C6—C7—C8—N4 | 177.78 (16) | C9—C10—N5—O8 | −42.9 (2) |
| C7—C8—C9—C10 | −1.3 (3) | C5—C10—N5—O8 | 140.79 (16) |
| N4—C8—C9—C10 | −179.93 (16) | C14—C13—N6—C15 | −56.2 (2) |
| C8—C9—C10—C5 | 2.4 (3) | C14—C13—N6—C11 | 176.34 (19) |
| C8—C9—C10—N5 | −173.72 (15) | C16—C15—N6—C13 | −64.0 (3) |
| C6—C5—C10—C9 | −1.2 (2) | C16—C15—N6—C11 | 63.6 (2) |
| C4—C5—C10—C9 | −179.92 (16) | C12—C11—N6—C13 | −64.7 (3) |
| C6—C5—C10—N5 | 174.67 (14) | C12—C11—N6—C15 | 165.7 (2) |
| C4—C5—C10—N5 | −4.1 (2) |
| H··· | ||||
| O10—H10···O2Wi | 0.82 | 2.05 | 2.792 (2) | 150 |
| O10—H10···O4ii | 0.82 | 2.49 | 3.0648 (19) | 129 |
| N6—H6···O1Wiii | 0.91 (3) | 1.95 (3) | 2.846 (2) | 170 (2) |
| N1—H1A···O10iv | 0.85 (2) | 2.05 (3) | 2.884 (2) | 166 (2) |
| N2—H2A···O2v | 0.83 (2) | 2.03 (2) | 2.847 (2) | 173 (2) |
| O1W—H2W···O2v | 0.91 (1) | 1.90 (2) | 2.7431 (19) | 154 (2) |
| O2W—H4W···O1Wvi | 0.93 (1) | 1.94 (2) | 2.796 (3) | 152 (3) |
| O1W—H1W···O3 | 0.91 (1) | 1.91 (1) | 2.7783 (17) | 160 (2) |
| O2W—H3W···O1 | 0.93 (1) | 1.89 (2) | 2.792 (2) | 162 (4) |
Hydrogen-bond geometry (Å, °)
| H⋯ | ||||
|---|---|---|---|---|
| O10—H10⋯O2 | 0.82 | 2.05 | 2.792 (2) | 150 |
| O10—H10⋯O4ii | 0.82 | 2.49 | 3.0648 (19) | 129 |
| N6—H6⋯O1 | 0.91 (3) | 1.95 (3) | 2.846 (2) | 170 (2) |
| N1—H1 | 0.85 (2) | 2.05 (3) | 2.884 (2) | 166 (2) |
| N2—H2 | 0.83 (2) | 2.03 (2) | 2.847 (2) | 173 (2) |
| O1 | 0.91 (1) | 1.90 (2) | 2.7431 (19) | 154 (2) |
| O2 | 0.93 (1) | 1.94 (2) | 2.796 (3) | 152 (3) |
| O1 | 0.91 (1) | 1.91 (1) | 2.7783 (17) | 160 (2) |
| O2 | 0.93 (1) | 1.89 (2) | 2.792 (2) | 162 (4) |
Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .