Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805039887/ci6717sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805039887/ci6717Isup2.hkl |
CCDC reference: 296538
Compound (I) was prepared by the reaction of 4-methoxybenzaldehyde (1 mmol) with malononitrile (2 mmol) and ammonium acetate (1 mmol) under microwave irradiation for 4 min (yield 95%; m.p. 573 K). Single crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of an ethanol and N,N-dimethylformamide solution (Ratio of solvents?).
The H atoms of the amino group were located in a difference Fourier map and refined isotropically [N—H = 0.79 (3)–1.00 (3) Å]. All other H atoms were placed in idealized positions and allowed to ride on their parent atoms, with C—H distances of 0.93 or 0.96 Å, and with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for other H atoms.
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.
C14H11N5O·C3H7NO | Z = 2 |
Mr = 338.37 | F(000) = 356 |
Triclinic, P1 | Dx = 1.272 Mg m−3 |
Hall symbol: -P 1 | Melting point: 573 K |
a = 6.9580 (13) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.5297 (18) Å | Cell parameters from 1237 reflections |
c = 14.695 (3) Å | θ = 2.3–25.6° |
α = 99.900 (3)° | µ = 0.09 mm−1 |
β = 102.505 (3)° | T = 294 K |
γ = 106.527 (3)° | Plate, colourless |
V = 883.1 (3) Å3 | 0.22 × 0.18 × 0.06 mm |
Bruker SMART CCD area-detector diffractometer | 3087 independent reflections |
Radiation source: fine-focus sealed tube | 1774 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
ϕ and ω scans | θmax = 25.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −6→8 |
Tmin = 0.976, Tmax = 0.995 | k = −11→11 |
4506 measured reflections | l = −14→17 |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0527P)2 + 0.1375P] where P = (Fo2 + 2Fc2)/3 |
3087 reflections | (Δ/σ)max = 0.001 |
245 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C14H11N5O·C3H7NO | γ = 106.527 (3)° |
Mr = 338.37 | V = 883.1 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.9580 (13) Å | Mo Kα radiation |
b = 9.5297 (18) Å | µ = 0.09 mm−1 |
c = 14.695 (3) Å | T = 294 K |
α = 99.900 (3)° | 0.22 × 0.18 × 0.06 mm |
β = 102.505 (3)° |
Bruker SMART CCD area-detector diffractometer | 3087 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1774 reflections with I > 2σ(I) |
Tmin = 0.976, Tmax = 0.995 | Rint = 0.026 |
4506 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.127 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.18 e Å−3 |
3087 reflections | Δρmin = −0.20 e Å−3 |
245 parameters |
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 | ||
O1 | 0.3300 (3) | 0.6323 (2) | 0.02945 (13) | 0.0636 (6) | |
N1 | 0.7128 (4) | 0.1842 (3) | 0.20947 (17) | 0.0634 (7) | |
N2 | 0.0778 (4) | 0.5285 (3) | 0.40879 (17) | 0.0658 (7) | |
N3 | 0.6437 (4) | 0.0727 (3) | 0.41777 (19) | 0.0555 (7) | |
H3A | 0.720 (4) | 0.060 (3) | 0.3788 (18) | 0.058 (8)* | |
H3B | 0.625 (4) | 0.004 (3) | 0.462 (2) | 0.076 (9)* | |
N4 | 0.4111 (3) | 0.1686 (2) | 0.47051 (14) | 0.0412 (5) | |
N5 | 0.1843 (4) | 0.2641 (3) | 0.52935 (17) | 0.0502 (6) | |
H5A | 0.105 (4) | 0.309 (3) | 0.5283 (18) | 0.051 (9)* | |
H5B | 0.177 (4) | 0.196 (3) | 0.572 (2) | 0.086 (10)* | |
C1 | 0.5031 (5) | 0.7464 (4) | 0.0204 (2) | 0.0716 (9) | |
H1A | 0.4579 | 0.7857 | −0.0333 | 0.107* | |
H1B | 0.6086 | 0.7039 | 0.0100 | 0.107* | |
H1C | 0.5596 | 0.8265 | 0.0782 | 0.107* | |
C2 | 0.3621 (4) | 0.5651 (3) | 0.10424 (17) | 0.0454 (7) | |
C3 | 0.5542 (4) | 0.5881 (3) | 0.16546 (18) | 0.0486 (7) | |
H3 | 0.6744 | 0.6534 | 0.1580 | 0.058* | |
C4 | 0.5676 (4) | 0.5134 (3) | 0.23843 (18) | 0.0466 (7) | |
H4A | 0.6981 | 0.5273 | 0.2788 | 0.056* | |
C5 | 0.3914 (4) | 0.4189 (3) | 0.25239 (16) | 0.0378 (6) | |
C6 | 0.1973 (4) | 0.3956 (3) | 0.18910 (17) | 0.0441 (6) | |
H6A | 0.0767 | 0.3314 | 0.1969 | 0.053* | |
C7 | 0.1833 (4) | 0.4669 (3) | 0.11536 (18) | 0.0484 (7) | |
H7A | 0.0538 | 0.4493 | 0.0728 | 0.058* | |
C8 | 0.4045 (4) | 0.3381 (3) | 0.33046 (17) | 0.0383 (6) | |
C9 | 0.5266 (4) | 0.2443 (3) | 0.33681 (17) | 0.0386 (6) | |
C10 | 0.6311 (4) | 0.2156 (3) | 0.26592 (19) | 0.0462 (7) | |
C11 | 0.5274 (4) | 0.1622 (3) | 0.40903 (18) | 0.0411 (6) | |
C12 | 0.2956 (4) | 0.2603 (3) | 0.46574 (17) | 0.0387 (6) | |
C13 | 0.2917 (4) | 0.3494 (3) | 0.39772 (16) | 0.0374 (6) | |
C14 | 0.1733 (4) | 0.4497 (3) | 0.40111 (17) | 0.0445 (7) | |
O2 | −0.0935 (3) | 0.9432 (2) | 0.33440 (16) | 0.0722 (6) | |
N6 | 0.0956 (4) | 0.8865 (3) | 0.23461 (17) | 0.0619 (7) | |
C15 | 0.1577 (7) | 0.9060 (5) | 0.1486 (3) | 0.1095 (14) | |
H15A | 0.1242 | 0.9896 | 0.1294 | 0.164* | |
H15B | 0.0846 | 0.8157 | 0.0978 | 0.164* | |
H15C | 0.3054 | 0.9258 | 0.1614 | 0.164* | |
C16 | 0.1581 (6) | 0.7810 (4) | 0.2847 (3) | 0.0931 (12) | |
H16A | 0.1450 | 0.8022 | 0.3489 | 0.140* | |
H16B | 0.3007 | 0.7914 | 0.2873 | 0.140* | |
H16C | 0.0699 | 0.6797 | 0.2509 | 0.140* | |
C17 | −0.0247 (5) | 0.9590 (3) | 0.2657 (2) | 0.0638 (8) | |
H17A | −0.0589 | 1.0273 | 0.2325 | 0.077* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0692 (13) | 0.0796 (15) | 0.0541 (12) | 0.0275 (12) | 0.0198 (10) | 0.0398 (11) |
N1 | 0.0709 (17) | 0.0822 (19) | 0.0698 (17) | 0.0452 (15) | 0.0436 (14) | 0.0390 (14) |
N2 | 0.0864 (19) | 0.0753 (18) | 0.0699 (17) | 0.0553 (16) | 0.0404 (14) | 0.0336 (14) |
N3 | 0.0611 (16) | 0.0737 (17) | 0.0714 (17) | 0.0478 (14) | 0.0438 (14) | 0.0441 (15) |
N4 | 0.0435 (12) | 0.0515 (13) | 0.0445 (13) | 0.0262 (11) | 0.0231 (10) | 0.0218 (10) |
N5 | 0.0625 (16) | 0.0641 (17) | 0.0515 (15) | 0.0417 (14) | 0.0343 (13) | 0.0264 (13) |
C1 | 0.089 (2) | 0.072 (2) | 0.070 (2) | 0.029 (2) | 0.0369 (19) | 0.0409 (18) |
C2 | 0.0569 (18) | 0.0525 (17) | 0.0365 (15) | 0.0260 (14) | 0.0155 (13) | 0.0198 (13) |
C3 | 0.0495 (17) | 0.0528 (17) | 0.0491 (16) | 0.0163 (14) | 0.0164 (14) | 0.0248 (14) |
C4 | 0.0412 (15) | 0.0525 (17) | 0.0469 (16) | 0.0147 (13) | 0.0108 (12) | 0.0177 (14) |
C5 | 0.0406 (15) | 0.0420 (15) | 0.0366 (15) | 0.0190 (12) | 0.0134 (12) | 0.0124 (12) |
C6 | 0.0402 (15) | 0.0515 (16) | 0.0467 (16) | 0.0184 (13) | 0.0161 (13) | 0.0178 (13) |
C7 | 0.0435 (16) | 0.0608 (18) | 0.0447 (16) | 0.0219 (14) | 0.0098 (13) | 0.0189 (14) |
C8 | 0.0369 (14) | 0.0397 (14) | 0.0399 (15) | 0.0141 (12) | 0.0102 (12) | 0.0126 (12) |
C9 | 0.0392 (14) | 0.0463 (15) | 0.0414 (15) | 0.0196 (12) | 0.0206 (12) | 0.0181 (12) |
C10 | 0.0470 (16) | 0.0540 (17) | 0.0534 (17) | 0.0259 (14) | 0.0235 (14) | 0.0267 (14) |
C11 | 0.0388 (14) | 0.0473 (16) | 0.0456 (16) | 0.0193 (13) | 0.0179 (12) | 0.0169 (13) |
C12 | 0.0413 (14) | 0.0439 (15) | 0.0366 (14) | 0.0198 (12) | 0.0144 (12) | 0.0107 (12) |
C13 | 0.0423 (15) | 0.0410 (15) | 0.0378 (14) | 0.0230 (12) | 0.0142 (12) | 0.0134 (12) |
C14 | 0.0546 (16) | 0.0502 (17) | 0.0407 (16) | 0.0250 (14) | 0.0201 (13) | 0.0203 (13) |
O2 | 0.0830 (16) | 0.0788 (15) | 0.0797 (15) | 0.0409 (13) | 0.0504 (13) | 0.0251 (12) |
N6 | 0.0653 (16) | 0.0543 (15) | 0.0770 (18) | 0.0257 (13) | 0.0393 (14) | 0.0102 (13) |
C15 | 0.125 (3) | 0.110 (3) | 0.104 (3) | 0.028 (3) | 0.079 (3) | 0.015 (2) |
C16 | 0.088 (3) | 0.083 (3) | 0.122 (3) | 0.052 (2) | 0.031 (2) | 0.020 (2) |
C17 | 0.065 (2) | 0.0528 (19) | 0.078 (2) | 0.0242 (16) | 0.0261 (18) | 0.0128 (17) |
O1—C2 | 1.373 (3) | C5—C8 | 1.488 (3) |
O1—C1 | 1.423 (3) | C6—C7 | 1.375 (3) |
N1—C10 | 1.147 (3) | C6—H6A | 0.93 |
N2—C14 | 1.143 (3) | C7—H7A | 0.93 |
N3—C11 | 1.336 (3) | C8—C13 | 1.397 (3) |
N3—H3A | 0.88 (3) | C8—C9 | 1.398 (3) |
N3—H3B | 1.00 (3) | C9—C11 | 1.423 (3) |
N4—C11 | 1.341 (3) | C9—C10 | 1.426 (3) |
N4—C12 | 1.345 (3) | C12—C13 | 1.419 (3) |
N5—C12 | 1.339 (3) | C13—C14 | 1.429 (3) |
N5—H5A | 0.79 (3) | O2—C17 | 1.221 (3) |
N5—H5B | 0.98 (3) | N6—C17 | 1.332 (3) |
C1—H1A | 0.96 | N6—C15 | 1.446 (4) |
C1—H1B | 0.96 | N6—C16 | 1.451 (4) |
C1—H1C | 0.96 | C15—H15A | 0.96 |
C2—C3 | 1.374 (3) | C15—H15B | 0.96 |
C2—C7 | 1.389 (3) | C15—H15C | 0.96 |
C3—C4 | 1.387 (3) | C16—H16A | 0.96 |
C3—H3 | 0.93 | C16—H16B | 0.96 |
C4—C5 | 1.378 (3) | C16—H16C | 0.96 |
C4—H4A | 0.93 | C17—H17A | 0.93 |
C5—C6 | 1.397 (3) | ||
C2—O1—C1 | 118.2 (2) | C9—C8—C5 | 120.5 (2) |
C11—N3—H3A | 121.8 (17) | C8—C9—C11 | 119.3 (2) |
C11—N3—H3B | 119.3 (16) | C8—C9—C10 | 121.4 (2) |
H3A—N3—H3B | 118 (2) | C11—C9—C10 | 118.9 (2) |
C11—N4—C12 | 118.6 (2) | N1—C10—C9 | 176.1 (3) |
C12—N5—H5A | 122.4 (19) | N3—C11—N4 | 116.7 (2) |
C12—N5—H5B | 121.0 (17) | N3—C11—C9 | 120.9 (2) |
H5A—N5—H5B | 116 (3) | N4—C11—C9 | 122.4 (2) |
O1—C1—H1A | 109.5 | N5—C12—N4 | 116.4 (2) |
O1—C1—H1B | 109.5 | N5—C12—C13 | 121.3 (2) |
H1A—C1—H1B | 109.5 | N4—C12—C13 | 122.3 (2) |
O1—C1—H1C | 109.5 | C8—C13—C12 | 119.4 (2) |
H1A—C1—H1C | 109.5 | C8—C13—C14 | 122.0 (2) |
H1B—C1—H1C | 109.5 | C12—C13—C14 | 118.6 (2) |
O1—C2—C3 | 124.6 (3) | N2—C14—C13 | 176.1 (3) |
O1—C2—C7 | 115.4 (2) | C17—N6—C15 | 120.8 (3) |
C3—C2—C7 | 120.0 (2) | C17—N6—C16 | 120.0 (3) |
C2—C3—C4 | 119.5 (3) | C15—N6—C16 | 119.1 (3) |
C2—C3—H3 | 120.2 | N6—C15—H15A | 109.5 |
C4—C3—H3 | 120.2 | N6—C15—H15B | 109.5 |
C5—C4—C3 | 121.4 (2) | H15A—C15—H15B | 109.5 |
C5—C4—H4A | 119.3 | N6—C15—H15C | 109.5 |
C3—C4—H4A | 119.3 | H15A—C15—H15C | 109.5 |
C4—C5—C6 | 118.5 (2) | H15B—C15—H15C | 109.5 |
C4—C5—C8 | 121.7 (2) | N6—C16—H16A | 109.5 |
C6—C5—C8 | 119.8 (2) | N6—C16—H16B | 109.5 |
C7—C6—C5 | 120.5 (2) | H16A—C16—H16B | 109.5 |
C7—C6—H6A | 119.8 | N6—C16—H16C | 109.5 |
C5—C6—H6A | 119.8 | H16A—C16—H16C | 109.5 |
C6—C7—C2 | 120.2 (2) | H16B—C16—H16C | 109.5 |
C6—C7—H7A | 119.9 | O2—C17—N6 | 125.2 (3) |
C2—C7—H7A | 119.9 | O2—C17—H17A | 117.4 |
C13—C8—C9 | 117.8 (2) | N6—C17—H17A | 117.4 |
C13—C8—C5 | 121.6 (2) | ||
C1—O1—C2—C3 | −7.3 (4) | C5—C8—C9—C10 | −4.0 (4) |
C1—O1—C2—C7 | 173.3 (2) | C12—N4—C11—N3 | 178.4 (2) |
O1—C2—C3—C4 | −179.7 (2) | C12—N4—C11—C9 | −2.4 (4) |
C7—C2—C3—C4 | −0.4 (4) | C8—C9—C11—N3 | −179.3 (2) |
C2—C3—C4—C5 | −1.5 (4) | C10—C9—C11—N3 | 7.8 (4) |
C3—C4—C5—C6 | 2.1 (4) | C8—C9—C11—N4 | 1.5 (4) |
C3—C4—C5—C8 | 179.9 (2) | C10—C9—C11—N4 | −171.3 (2) |
C4—C5—C6—C7 | −0.7 (4) | C11—N4—C12—N5 | −179.2 (2) |
C8—C5—C6—C7 | −178.6 (2) | C11—N4—C12—C13 | 0.4 (4) |
C5—C6—C7—C2 | −1.2 (4) | C9—C8—C13—C12 | −3.4 (3) |
O1—C2—C7—C6 | −178.9 (2) | C5—C8—C13—C12 | 174.7 (2) |
C3—C2—C7—C6 | 1.7 (4) | C9—C8—C13—C14 | 175.9 (2) |
C4—C5—C8—C13 | 126.0 (3) | C5—C8—C13—C14 | −6.0 (4) |
C6—C5—C8—C13 | −56.1 (3) | N5—C12—C13—C8 | −177.8 (2) |
C4—C5—C8—C9 | −55.9 (3) | N4—C12—C13—C8 | 2.6 (4) |
C6—C5—C8—C9 | 121.9 (3) | N5—C12—C13—C14 | 2.9 (4) |
C13—C8—C9—C11 | 1.5 (4) | N4—C12—C13—C14 | −176.7 (2) |
C5—C8—C9—C11 | −176.7 (2) | C15—N6—C17—O2 | 175.9 (3) |
C13—C8—C9—C10 | 174.2 (2) | C16—N6—C17—O2 | −1.3 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O2i | 0.88 (3) | 2.07 (3) | 2.846 (3) | 147 (2) |
N3—H3B···N4ii | 1.00 (3) | 2.04 (3) | 3.033 (3) | 168 (2) |
N5—H5A···N2iii | 0.79 (3) | 2.45 (3) | 3.195 (3) | 158 (2) |
N5—H5B···O2iii | 0.98 (3) | 2.13 (3) | 3.083 (3) | 166 (2) |
C6—H6A···N1iv | 0.93 | 2.59 | 3.506 (4) | 171 |
C7—H7A···O1v | 0.93 | 2.58 | 3.503 (4) | 170 |
C17—H17A···N1vi | 0.93 | 2.48 | 3.288 (4) | 145 |
Symmetry codes: (i) x+1, y−1, z; (ii) −x+1, −y, −z+1; (iii) −x, −y+1, −z+1; (iv) x−1, y, z; (v) −x, −y+1, −z; (vi) x−1, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C14H11N5O·C3H7NO |
Mr | 338.37 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 294 |
a, b, c (Å) | 6.9580 (13), 9.5297 (18), 14.695 (3) |
α, β, γ (°) | 99.900 (3), 102.505 (3), 106.527 (3) |
V (Å3) | 883.1 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.22 × 0.18 × 0.06 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.976, 0.995 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4506, 3087, 1774 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.127, 1.00 |
No. of reflections | 3087 |
No. of parameters | 245 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.18, −0.20 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O2i | 0.88 (3) | 2.07 (3) | 2.846 (3) | 147 (2) |
N3—H3B···N4ii | 1.00 (3) | 2.04 (3) | 3.033 (3) | 168 (2) |
N5—H5A···N2iii | 0.79 (3) | 2.45 (3) | 3.195 (3) | 158 (2) |
N5—H5B···O2iii | 0.98 (3) | 2.13 (3) | 3.083 (3) | 166 (2) |
C6—H6A···N1iv | 0.93 | 2.59 | 3.506 (4) | 171 |
C7—H7A···O1v | 0.93 | 2.58 | 3.503 (4) | 170 |
C17—H17A···N1vi | 0.93 | 2.48 | 3.288 (4) | 145 |
Symmetry codes: (i) x+1, y−1, z; (ii) −x+1, −y, −z+1; (iii) −x, −y+1, −z+1; (iv) x−1, y, z; (v) −x, −y+1, −z; (vi) x−1, y+1, z. |
3,5-Dicyanopyridine derivatives exhibit a wide range of bioactivities, such as antifungal, insecticidal, herbicidal, miticidal, nematocidal and antimicrobial activity (Gante & Lust, 1971). Some substituted 3,5-dicyanopyridines have recently been reported to exhibit a high conductance-type calcium-activated K-channel opening effect (Hirochika et al., 2003) and to be adenosine receptor-selective ligands (Rosentreter et al., 2002), which are useful in the treatment of many diseases. More importantly, they are also versatile intermediates in organic synthesis (Castedo et al., 1984). As a consequence, much attention has been paid to the synthesis of these derivatives during the past 50 years. We report here the crystal structure of the title compound, (I).
The 2,6-diamino-1,4-dihydropyridine-3,5-dicarbonitrile fragment of (I) (atoms C8–C14/N1–N5) is almost planar, with an r.m.s. deviation of 0.076 Å (Fig. 1). The dihedral angle between the pyridine and benzene planes is 56.07 (8)°.
The crystal packing shows that intermolecular N—H···O, N—H···N, C—H···O and C—H···N hydrogen bonds (Table 1) form a three-dimensional network (Fig. 2).