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organic compounds
(5-Hydroxy-3-methyl-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl)(pyridin-4-yl)methanone monohydrate
aDepartment of Chemistry, School of Science, Payame Noor University (PNU), Ardakan, Yazd, Iran, bDepartment of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran, cX-ray Crystallography Lab., Plasma Physics Research Center, Science and Research Branch, Islamic Azad University, Tehran, Iran, dDepartment of Chemistry, Azarbaijan University of Tarbiat Moallem, Tabriz, Iran, and eDepartment of Physics, University of Sargodha, Punjab, Pakistan
*Correspondence e-mail: rkia@srbiau.ac.ir, zsrkk@yahoo.com, dmntahir_uos@yahoo.com
In the title compound, C16H15N3O2·H2O, the mean plane of the approximately planar pyrazole ring [maximum deviation = 0.0474 (18) Å] makes dihedral angles of 86.32 (11) and 45.04 (10)° with the phenyl and pyridine rings, respectively. The dihedral angle between the phenyl and pyridine rings is 69.62 (11)°. In the crystal, intermolecular O—H⋯O and O—H⋯N hydrogen bonds connect the components into chains along [010]. The is further stabilized by π–π stacking interactions with centroid–centroid distances of 3.7730 (12) Å.
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2005); cell SAINT (Bruker, 2005
); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008
); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and PLATON (Spek, 2009
); software used to prepare material for publication: SHELXTL and PLATON.
Supporting information
https://doi.org/10.1107/S160053681005275X/lh5187sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681005275X/lh5187Isup2.hkl
The title compound was synthesized by adding isoniazide (2 mmol) to a solution of benzoylacetone (2 mmol) in ethanol (20 ml). The mixture was refluxed with stirring for half an hour. The resultant solution was filtered and the white single crystals suitable for X-ray
were recrystallized from ethanol by slow evaporation of the solvents at room temperature over several days.The H atoms of the water and hydroxy groups were located in a difference Fourier map and constraied to refine on the parent atom with Uiso(H) = 1.5 Ueq(O), see Table 1. The remaining H atoms were positioned geometrically with C—H = 0.93-0.97 Å and included in a riding-model approximation with Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating group model was used for the methyl group.
The
of the title compound, Fig. 1, comprises a substituted pyrazole molecule and a solvent water molecule. The bond lengths (Allen et al., 1987) and angles are within the normal ranges. The dihedral angle the mean plane of the pyrazole ring makes with the phenyl and pyridine rings are 86.32 (11) and 45.04 (10)°, respectively. The dihedral angle between the phenyl ring and the pyridine ring is 69.62 (11)Å.In the π–π stacking interactions [Cg1···Cg1iv = 3.7730 (11)Å, (iv) -x, 1 - y, -z, Cg1 is the centroid of the C12-C16/N3 ring].
intermolecular O—H···O and O—H···N hydrogen bonds connect the components of the structure to form one-dimensional chains along [0 1 0]. The is further stabilized by intermolecularFor standard values of bond lengths, see: Allen et al. (1987).
Data collection: APEX2 (Bruker, 2005); cell
SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).C16H15N3O2·H2O | F(000) = 632 |
Mr = 299.33 | Dx = 1.324 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2540 reflections |
a = 16.9676 (10) Å | θ = 2.5–27.5° |
b = 7.0266 (5) Å | µ = 0.09 mm−1 |
c = 12.6135 (6) Å | T = 296 K |
β = 93.004 (3)° | Prism, white |
V = 1501.77 (16) Å3 | 0.32 × 0.24 × 0.18 mm |
Z = 4 |
Bruker SMART APEXII CCD area-detector diffractometer | 3059 independent reflections |
Radiation source: fine-focus sealed tube | 1916 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
φ and ω scans | θmax = 26.5°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −18→21 |
Tmin = 0.971, Tmax = 0.983 | k = −7→8 |
8525 measured reflections | l = −15→14 |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0554P)2] where P = (Fo2 + 2Fc2)/3 |
3059 reflections | (Δ/σ)max < 0.001 |
200 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C16H15N3O2·H2O | V = 1501.77 (16) Å3 |
Mr = 299.33 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.9676 (10) Å | µ = 0.09 mm−1 |
b = 7.0266 (5) Å | T = 296 K |
c = 12.6135 (6) Å | 0.32 × 0.24 × 0.18 mm |
β = 93.004 (3)° |
Bruker SMART APEXII CCD area-detector diffractometer | 3059 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 1916 reflections with I > 2σ(I) |
Tmin = 0.971, Tmax = 0.983 | Rint = 0.038 |
8525 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.15 e Å−3 |
3059 reflections | Δρmin = −0.18 e Å−3 |
200 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | 0.32045 (8) | 0.3424 (2) | −0.01490 (10) | 0.0461 (4) | |
H1 | 0.2849 | 0.2478 | −0.0322 | 0.069* | |
O2 | 0.22503 (8) | 0.70361 (19) | 0.00147 (10) | 0.0455 (4) | |
O1W | 0.21323 (8) | 0.4293 (2) | 0.41563 (10) | 0.0522 (4) | |
H1W1 | 0.2123 | 0.5449 | 0.4498 | 0.078* | |
H2W1 | 0.1656 | 0.3911 | 0.4143 | 0.078* | |
N1 | 0.17899 (8) | 0.3038 (2) | 0.15669 (11) | 0.0339 (4) | |
N2 | 0.22186 (8) | 0.4400 (2) | 0.10150 (11) | 0.0347 (4) | |
N3 | −0.05005 (9) | 0.7733 (2) | 0.10396 (13) | 0.0431 (4) | |
C1 | 0.36077 (10) | 0.5444 (3) | 0.12956 (14) | 0.0370 (5) | |
C2 | 0.35148 (13) | 0.6223 (3) | 0.22873 (16) | 0.0544 (6) | |
H2 | 0.3115 | 0.5788 | 0.2703 | 0.065* | |
C3 | 0.40176 (17) | 0.7653 (4) | 0.2661 (2) | 0.0726 (8) | |
H3A | 0.3947 | 0.8188 | 0.3323 | 0.087* | |
C4 | 0.46131 (16) | 0.8286 (4) | 0.2071 (3) | 0.0770 (8) | |
H4 | 0.4951 | 0.9238 | 0.2333 | 0.092* | |
C5 | 0.47118 (14) | 0.7520 (4) | 0.1099 (2) | 0.0726 (8) | |
H5 | 0.5119 | 0.7947 | 0.0694 | 0.087* | |
C6 | 0.42080 (12) | 0.6104 (3) | 0.07061 (17) | 0.0521 (6) | |
H6 | 0.4277 | 0.5596 | 0.0036 | 0.062* | |
C7 | 0.30659 (10) | 0.3854 (3) | 0.09099 (13) | 0.0359 (5) | |
C8 | 0.31075 (11) | 0.2087 (3) | 0.16286 (16) | 0.0449 (5) | |
H8A | 0.3310 | 0.1000 | 0.1255 | 0.054* | |
H8B | 0.3443 | 0.2320 | 0.2262 | 0.054* | |
C9 | 0.22789 (11) | 0.1762 (3) | 0.19037 (13) | 0.0339 (4) | |
C10 | 0.20331 (12) | 0.0106 (3) | 0.25333 (15) | 0.0469 (5) | |
H10A | 0.1476 | 0.0176 | 0.2628 | 0.070* | |
H10B | 0.2314 | 0.0116 | 0.3214 | 0.070* | |
H10C | 0.2150 | −0.1048 | 0.2166 | 0.070* | |
C11 | 0.18790 (11) | 0.5957 (3) | 0.05705 (13) | 0.0334 (4) | |
C12 | 0.10340 (10) | 0.6415 (2) | 0.07655 (13) | 0.0297 (4) | |
C13 | 0.07060 (11) | 0.6357 (3) | 0.17484 (14) | 0.0375 (5) | |
H13 | 0.0990 | 0.5858 | 0.2335 | 0.045* | |
C14 | −0.00432 (12) | 0.7045 (3) | 0.18447 (15) | 0.0430 (5) | |
H14 | −0.0247 | 0.7031 | 0.2515 | 0.052* | |
C15 | −0.01844 (11) | 0.7738 (3) | 0.00927 (15) | 0.0407 (5) | |
H15 | −0.0493 | 0.8176 | −0.0488 | 0.049* | |
C16 | 0.05681 (11) | 0.7135 (3) | −0.00760 (14) | 0.0361 (5) | |
H16 | 0.0764 | 0.7210 | −0.0750 | 0.043* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0399 (8) | 0.0500 (9) | 0.0490 (8) | −0.0025 (7) | 0.0074 (6) | −0.0062 (7) |
O2 | 0.0370 (8) | 0.0445 (9) | 0.0556 (8) | 0.0018 (7) | 0.0082 (6) | 0.0166 (7) |
O1W | 0.0428 (8) | 0.0447 (9) | 0.0690 (9) | −0.0001 (7) | 0.0023 (6) | −0.0063 (7) |
N1 | 0.0297 (9) | 0.0353 (9) | 0.0368 (8) | −0.0024 (8) | 0.0008 (7) | 0.0024 (7) |
N2 | 0.0240 (8) | 0.0362 (9) | 0.0438 (8) | 0.0016 (7) | 0.0022 (6) | 0.0106 (7) |
N3 | 0.0319 (9) | 0.0421 (10) | 0.0553 (11) | 0.0033 (8) | 0.0027 (8) | −0.0013 (8) |
C1 | 0.0274 (10) | 0.0373 (11) | 0.0457 (11) | 0.0028 (9) | −0.0031 (8) | 0.0043 (9) |
C2 | 0.0458 (13) | 0.0606 (16) | 0.0564 (13) | 0.0085 (12) | −0.0017 (10) | −0.0066 (11) |
C3 | 0.0676 (18) | 0.0689 (19) | 0.0786 (17) | 0.0129 (16) | −0.0232 (14) | −0.0247 (14) |
C4 | 0.0537 (17) | 0.0506 (17) | 0.123 (2) | −0.0011 (14) | −0.0303 (16) | −0.0094 (16) |
C5 | 0.0484 (15) | 0.0663 (19) | 0.102 (2) | −0.0183 (14) | −0.0027 (14) | 0.0144 (16) |
C6 | 0.0413 (12) | 0.0551 (15) | 0.0598 (13) | −0.0080 (11) | 0.0028 (10) | 0.0046 (11) |
C7 | 0.0253 (10) | 0.0393 (12) | 0.0434 (11) | 0.0041 (9) | 0.0048 (8) | 0.0036 (9) |
C8 | 0.0352 (11) | 0.0387 (12) | 0.0605 (12) | 0.0049 (10) | 0.0006 (9) | 0.0118 (10) |
C9 | 0.0355 (11) | 0.0314 (11) | 0.0345 (9) | 0.0005 (9) | 0.0000 (8) | −0.0005 (8) |
C10 | 0.0472 (12) | 0.0370 (12) | 0.0567 (12) | 0.0009 (11) | 0.0055 (9) | 0.0069 (10) |
C11 | 0.0294 (10) | 0.0355 (11) | 0.0349 (10) | 0.0017 (9) | −0.0009 (8) | 0.0008 (9) |
C12 | 0.0289 (10) | 0.0249 (10) | 0.0351 (10) | −0.0014 (8) | 0.0004 (8) | −0.0009 (8) |
C13 | 0.0348 (11) | 0.0420 (12) | 0.0355 (10) | 0.0022 (10) | −0.0015 (8) | 0.0012 (9) |
C14 | 0.0381 (12) | 0.0480 (13) | 0.0431 (11) | −0.0005 (10) | 0.0053 (9) | −0.0035 (9) |
C15 | 0.0343 (11) | 0.0386 (12) | 0.0480 (12) | 0.0020 (10) | −0.0095 (9) | 0.0048 (9) |
C16 | 0.0363 (11) | 0.0358 (11) | 0.0360 (10) | 0.0017 (9) | −0.0013 (8) | 0.0013 (8) |
O1—C7 | 1.401 (2) | C5—C6 | 1.386 (3) |
O1—H1 | 0.9166 | C5—H5 | 0.9300 |
O2—C11 | 1.229 (2) | C6—H6 | 0.9300 |
O1W—H1W1 | 0.9200 | C7—C8 | 1.536 (3) |
O1W—H2W1 | 0.8517 | C8—C9 | 1.483 (3) |
N1—C9 | 1.279 (2) | C8—H8A | 0.9700 |
N1—N2 | 1.408 (2) | C8—H8B | 0.9700 |
N2—C11 | 1.345 (2) | C9—C10 | 1.481 (3) |
N2—C7 | 1.501 (2) | C10—H10A | 0.9600 |
N3—C15 | 1.334 (2) | C10—H10B | 0.9600 |
N3—C14 | 1.336 (2) | C10—H10C | 0.9600 |
C1—C6 | 1.373 (3) | C11—C12 | 1.502 (2) |
C1—C2 | 1.382 (3) | C12—C16 | 1.386 (2) |
C1—C7 | 1.511 (3) | C12—C13 | 1.386 (2) |
C2—C3 | 1.384 (3) | C13—C14 | 1.371 (3) |
C2—H2 | 0.9300 | C13—H13 | 0.9300 |
C3—C4 | 1.360 (4) | C14—H14 | 0.9300 |
C3—H3A | 0.9300 | C15—C16 | 1.372 (3) |
C4—C5 | 1.358 (4) | C15—H15 | 0.9300 |
C4—H4 | 0.9300 | C16—H16 | 0.9300 |
C7—O1—H1 | 104.0 | C9—C8—H8A | 110.9 |
H1W1—O1W—H2W1 | 104.4 | C7—C8—H8A | 110.9 |
C9—N1—N2 | 107.33 (14) | C9—C8—H8B | 110.9 |
C11—N2—N1 | 122.54 (15) | C7—C8—H8B | 110.9 |
C11—N2—C7 | 124.25 (15) | H8A—C8—H8B | 108.9 |
N1—N2—C7 | 113.06 (13) | N1—C9—C10 | 122.21 (17) |
C15—N3—C14 | 115.90 (17) | N1—C9—C8 | 114.87 (16) |
C6—C1—C2 | 118.6 (2) | C10—C9—C8 | 122.91 (17) |
C6—C1—C7 | 122.12 (17) | C9—C10—H10A | 109.5 |
C2—C1—C7 | 119.22 (17) | C9—C10—H10B | 109.5 |
C1—C2—C3 | 119.9 (2) | H10A—C10—H10B | 109.5 |
C1—C2—H2 | 120.1 | C9—C10—H10C | 109.5 |
C3—C2—H2 | 120.1 | H10A—C10—H10C | 109.5 |
C4—C3—C2 | 120.9 (2) | H10B—C10—H10C | 109.5 |
C4—C3—H3A | 119.5 | O2—C11—N2 | 121.24 (17) |
C2—C3—H3A | 119.5 | O2—C11—C12 | 118.90 (16) |
C5—C4—C3 | 119.6 (2) | N2—C11—C12 | 119.85 (16) |
C5—C4—H4 | 120.2 | C16—C12—C13 | 117.15 (17) |
C3—C4—H4 | 120.2 | C16—C12—C11 | 117.65 (15) |
C4—C5—C6 | 120.3 (2) | C13—C12—C11 | 124.86 (16) |
C4—C5—H5 | 119.9 | C14—C13—C12 | 119.10 (17) |
C6—C5—H5 | 119.9 | C14—C13—H13 | 120.4 |
C1—C6—C5 | 120.7 (2) | C12—C13—H13 | 120.4 |
C1—C6—H6 | 119.7 | N3—C14—C13 | 124.36 (18) |
C5—C6—H6 | 119.7 | N3—C14—H14 | 117.8 |
O1—C7—N2 | 110.42 (13) | C13—C14—H14 | 117.8 |
O1—C7—C1 | 109.67 (14) | N3—C15—C16 | 123.97 (17) |
N2—C7—C1 | 110.60 (15) | N3—C15—H15 | 118.0 |
O1—C7—C8 | 112.56 (16) | C16—C15—H15 | 118.0 |
N2—C7—C8 | 99.74 (14) | C15—C16—C12 | 119.47 (17) |
C1—C7—C8 | 113.51 (15) | C15—C16—H16 | 120.3 |
C9—C8—C7 | 104.34 (15) | C12—C16—H16 | 120.3 |
C9—N1—N2—C11 | −179.02 (16) | N2—C7—C8—C9 | 7.23 (18) |
C9—N1—N2—C7 | 5.31 (18) | C1—C7—C8—C9 | 124.87 (16) |
C6—C1—C2—C3 | 0.6 (3) | N2—N1—C9—C10 | 179.31 (16) |
C7—C1—C2—C3 | 178.63 (19) | N2—N1—C9—C8 | 0.2 (2) |
C1—C2—C3—C4 | −1.1 (4) | C7—C8—C9—N1 | −5.2 (2) |
C2—C3—C4—C5 | 0.7 (4) | C7—C8—C9—C10 | 175.69 (17) |
C3—C4—C5—C6 | 0.2 (4) | N1—N2—C11—O2 | −173.53 (15) |
C2—C1—C6—C5 | 0.2 (3) | C7—N2—C11—O2 | 1.7 (3) |
C7—C1—C6—C5 | −177.7 (2) | N1—N2—C11—C12 | 7.4 (2) |
C4—C5—C6—C1 | −0.6 (4) | C7—N2—C11—C12 | −177.38 (15) |
C11—N2—C7—O1 | −64.9 (2) | O2—C11—C12—C16 | 39.6 (2) |
N1—N2—C7—O1 | 110.71 (15) | N2—C11—C12—C16 | −141.39 (18) |
C11—N2—C7—C1 | 56.7 (2) | O2—C11—C12—C13 | −133.48 (19) |
N1—N2—C7—C1 | −127.72 (15) | N2—C11—C12—C13 | 45.6 (3) |
C11—N2—C7—C8 | 176.49 (17) | C16—C12—C13—C14 | −1.5 (3) |
N1—N2—C7—C8 | −7.92 (18) | C11—C12—C13—C14 | 171.52 (18) |
C6—C1—C7—O1 | −8.6 (2) | C15—N3—C14—C13 | −0.4 (3) |
C2—C1—C7—O1 | 173.52 (17) | C12—C13—C14—N3 | 2.0 (3) |
C6—C1—C7—N2 | −130.57 (19) | C14—N3—C15—C16 | −1.7 (3) |
C2—C1—C7—N2 | 51.5 (2) | N3—C15—C16—C12 | 2.1 (3) |
C6—C1—C7—C8 | 118.3 (2) | C13—C12—C16—C15 | −0.4 (3) |
C2—C1—C7—C8 | −59.6 (2) | C11—C12—C16—C15 | −173.97 (17) |
O1—C7—C8—C9 | −109.82 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O1Wi | 0.92 | 1.84 | 2.7490 (19) | 173 |
O1W—H1W1···O2ii | 0.92 | 1.89 | 2.8003 (19) | 169 |
O1W—H2W1···N3iii | 0.85 | 2.13 | 2.976 (2) | 173 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+3/2, z+1/2; (iii) −x, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C16H15N3O2·H2O |
Mr | 299.33 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 16.9676 (10), 7.0266 (5), 12.6135 (6) |
β (°) | 93.004 (3) |
V (Å3) | 1501.77 (16) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.32 × 0.24 × 0.18 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.971, 0.983 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8525, 3059, 1916 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.121, 1.03 |
No. of reflections | 3059 |
No. of parameters | 200 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.15, −0.18 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O1Wi | 0.92 | 1.84 | 2.7490 (19) | 172.6 |
O1W—H1W1···O2ii | 0.92 | 1.89 | 2.8003 (19) | 169.0 |
O1W—H2W1···N3iii | 0.85 | 2.13 | 2.976 (2) | 173.2 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+3/2, z+1/2; (iii) −x, y−1/2, −z+1/2. |
Acknowledgements
HK and FF thank the PNU for the financial support. RK thanks the Science and Research Branch, Islamic Azad University. MNT thanks the University of Sargodha, Pakistan, for the research facilities.
References
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The asymmetric unit of the title compound, Fig. 1, comprises a substituted pyrazole molecule and a solvent water molecule. The bond lengths (Allen et al., 1987) and angles are within the normal ranges. The dihedral angle the mean plane of the pyrazole ring makes with the phenyl and pyridine rings are 86.32 (11) and 45.04 (10)°, respectively. The dihedral angle between the phenyl ring and the pyridine ring is 69.62 (11)Å.
In the crystal structure, intermolecular O—H···O and O—H···N hydrogen bonds connect the components of the structure to form one-dimensional chains along [0 1 0]. The crystal structure is further stabilized by intermolecular π–π stacking interactions [Cg1···Cg1iv = 3.7730 (11)Å, (iv) -x, 1 - y, -z, Cg1 is the centroid of the C12-C16/N3 ring].