5-Methyl-N'-[(3Z)-2-oxo-2,3-dihydro-1H-indol-3-yl-idene]-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide.

In the title compound, C18H14N6O2, the benzene ring is slightly twisted out of the plane of the 1,2,3-triazole ring (r.m.s. deviation = 0.010 Å), forming a dihedral angle of 6.20 (13)°. The nine non-H ring atoms of the fused five- and six-membered ring system are almost coplanar (r.m.s. deviation = 0.032 Å). The near coplanarity in the central residue is consolidated by an intra-molecular bifurcated N-H⋯(O,N) hydrogen bond. The conformation about the N=C bond is Z. In the crystal, supra-molecular chains along [101] are sustained by N-H⋯O hydrogen bonds and C-H⋯O inter-actions. These are consolidated into a three-dimensional architecture by C-H⋯π and π-π inter-actions; the latter occur between centrosymmetrically related 1,2,3-triazole rings [centroid-centroid distance = 3.6056 (14) Å].

Related literature

For the biological activity of 1,2,3-triazoles, see: Abdel-Wahab et al. (2012 ▶); Jordão et al. (2011 ▶).

Experimental

Crystal data

C18H14N6O2

M = 346.35

Monoclinic,

a = 7.1835 (8) Å

b = 18.620 (2) Å

c = 12.2949 (11) Å

β = 101.676 (11)°

V = 1610.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 295 K

0.25 × 0.05 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.971, T max = 1.000

8876 measured reflections

3715 independent reflections

2131 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.147

S = 1.03

3715 reflections

244 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813007502/hb7059sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007502/hb7059Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813007502/hb7059Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H14N6O2	F(000) = 720
Mr = 346.35	Dx = 1.428 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1697 reflections
a = 7.1835 (8) Å	θ = 2.9–27.5°
b = 18.620 (2) Å	µ = 0.10 mm−1
c = 12.2949 (11) Å	T = 295 K
β = 101.676 (11)°	Prism, yellow
V = 1610.5 (3) Å3	0.25 × 0.05 × 0.05 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	3715 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2131 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.039
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 3.0°
ω scan	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −21→24
Tmin = 0.971, Tmax = 1.000	l = −15→16
8876 measured reflections

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0482P)2 + 0.2228P] where P = (Fo2 + 2Fc2)/3
3715 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 0.16 e Å−3
2 restraints	Δρmin = −0.20 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
O1	0.5195 (3)	0.58729 (9)	0.26022 (12)	0.0597 (5)
O2	0.8162 (3)	0.71122 (10)	0.60828 (12)	0.0613 (5)
N1	0.7254 (2)	0.41347 (10)	0.47664 (13)	0.0418 (5)
N2	0.8247 (3)	0.45889 (11)	0.55553 (14)	0.0485 (5)
N3	0.7912 (3)	0.52406 (11)	0.52030 (14)	0.0461 (5)
N4	0.6750 (3)	0.64843 (10)	0.41239 (14)	0.0446 (5)
N5	0.6338 (3)	0.71428 (10)	0.36535 (14)	0.0429 (5)
N6	0.8130 (3)	0.83398 (12)	0.58399 (15)	0.0517 (5)
C1	0.7454 (3)	0.33768 (13)	0.49580 (18)	0.0430 (6)
C2	0.7219 (4)	0.28982 (14)	0.4094 (2)	0.0553 (7)
H2	0.6931	0.3062	0.3365	0.066*
C3	0.7413 (4)	0.21701 (15)	0.4314 (2)	0.0655 (8)
H3	0.7229	0.1844	0.3729	0.079*
C4	0.7873 (4)	0.19263 (16)	0.5383 (3)	0.0670 (8)
H4A	0.8008	0.1437	0.5527	0.080*
C5	0.8131 (4)	0.24064 (16)	0.6236 (2)	0.0669 (8)
H5	0.8457	0.2240	0.6962	0.080*
C6	0.7917 (4)	0.31390 (15)	0.60440 (19)	0.0558 (7)
H6A	0.8081	0.3462	0.6632	0.067*
C7	0.6714 (3)	0.52181 (12)	0.41830 (16)	0.0390 (5)
C8	0.6253 (3)	0.45209 (13)	0.39001 (16)	0.0397 (5)
C9	0.4854 (3)	0.42228 (13)	0.29457 (18)	0.0509 (6)
H9A	0.3960	0.4590	0.2642	0.076*
H9B	0.4190	0.3828	0.3195	0.076*
H9C	0.5509	0.4059	0.2385	0.076*
C10	0.6140 (3)	0.58757 (12)	0.35507 (17)	0.0416 (6)
C11	0.7793 (3)	0.76558 (13)	0.55151 (18)	0.0466 (6)
C12	0.6838 (3)	0.76850 (12)	0.43033 (16)	0.0395 (5)
C13	0.6616 (3)	0.84409 (12)	0.40176 (16)	0.0392 (5)
C14	0.5752 (3)	0.88056 (13)	0.30717 (17)	0.0464 (6)
H14	0.5144	0.8557	0.2443	0.056*
C15	0.5807 (3)	0.95496 (14)	0.30778 (19)	0.0531 (7)
H15	0.5234	0.9804	0.2447	0.064*
C16	0.6707 (4)	0.99165 (14)	0.4013 (2)	0.0595 (7)
H16	0.6748	1.0416	0.3997	0.071*
C17	0.7551 (4)	0.95587 (14)	0.49753 (19)	0.0565 (7)
H17	0.8150	0.9809	0.5604	0.068*
C18	0.7469 (3)	0.88237 (14)	0.49662 (17)	0.0438 (6)
H4	0.739 (3)	0.6463 (14)	0.4827 (10)	0.063 (8)*
H6	0.876 (4)	0.8480 (15)	0.6497 (13)	0.087 (10)*

	U11	U22	U33	U12	U13	U23
O1	0.0920 (12)	0.0383 (11)	0.0371 (8)	0.0049 (9)	−0.0148 (8)	−0.0004 (7)
O2	0.0829 (12)	0.0428 (11)	0.0470 (9)	−0.0027 (10)	−0.0136 (8)	0.0080 (8)
N1	0.0514 (11)	0.0315 (11)	0.0394 (9)	0.0026 (9)	0.0015 (8)	0.0026 (8)
N2	0.0584 (12)	0.0370 (12)	0.0436 (10)	0.0009 (10)	−0.0049 (9)	0.0016 (9)
N3	0.0559 (11)	0.0359 (12)	0.0417 (10)	0.0019 (10)	−0.0020 (9)	0.0023 (8)
N4	0.0587 (11)	0.0312 (12)	0.0382 (10)	0.0008 (10)	−0.0041 (9)	0.0025 (8)
N5	0.0538 (11)	0.0290 (11)	0.0416 (10)	0.0017 (9)	−0.0004 (8)	0.0019 (8)
N6	0.0685 (13)	0.0405 (13)	0.0380 (10)	−0.0032 (11)	−0.0087 (9)	−0.0057 (9)
C1	0.0489 (12)	0.0282 (13)	0.0512 (13)	0.0054 (11)	0.0087 (10)	0.0081 (10)
C2	0.0716 (16)	0.0370 (16)	0.0564 (14)	0.0058 (14)	0.0105 (12)	0.0031 (12)
C3	0.0800 (19)	0.0370 (16)	0.0777 (18)	0.0060 (15)	0.0119 (15)	−0.0003 (14)
C4	0.0746 (18)	0.0349 (16)	0.090 (2)	0.0088 (14)	0.0119 (16)	0.0152 (15)
C5	0.0797 (19)	0.0528 (19)	0.0660 (16)	0.0160 (16)	0.0095 (14)	0.0251 (15)
C6	0.0688 (16)	0.0438 (16)	0.0517 (14)	0.0122 (14)	0.0051 (12)	0.0096 (12)
C7	0.0468 (12)	0.0318 (13)	0.0350 (10)	0.0039 (10)	0.0005 (9)	−0.0010 (9)
C8	0.0458 (12)	0.0350 (14)	0.0364 (11)	0.0028 (11)	0.0041 (9)	0.0036 (10)
C9	0.0614 (14)	0.0355 (14)	0.0495 (13)	−0.0020 (12)	−0.0038 (11)	−0.0025 (11)
C10	0.0505 (12)	0.0317 (13)	0.0395 (11)	0.0029 (11)	0.0018 (10)	−0.0014 (10)
C11	0.0546 (13)	0.0393 (15)	0.0399 (12)	−0.0006 (12)	−0.0047 (10)	0.0005 (11)
C12	0.0438 (12)	0.0315 (13)	0.0387 (11)	−0.0017 (10)	−0.0021 (9)	−0.0024 (10)
C13	0.0440 (11)	0.0333 (13)	0.0379 (11)	−0.0030 (11)	0.0026 (9)	−0.0032 (9)
C14	0.0548 (13)	0.0380 (14)	0.0422 (12)	−0.0026 (12)	0.0003 (10)	−0.0018 (11)
C15	0.0683 (16)	0.0372 (15)	0.0491 (13)	0.0008 (13)	0.0003 (12)	0.0063 (11)
C16	0.0813 (18)	0.0311 (14)	0.0621 (16)	−0.0035 (14)	0.0051 (14)	−0.0005 (12)
C17	0.0749 (17)	0.0382 (15)	0.0510 (14)	−0.0083 (14)	−0.0004 (12)	−0.0101 (12)
C18	0.0532 (13)	0.0348 (14)	0.0402 (11)	−0.0026 (11)	0.0022 (10)	−0.0019 (10)

O1—C10	1.225 (2)	C5—C6	1.388 (4)
O2—C11	1.228 (3)	C5—H5	0.9300
N1—C8	1.363 (2)	C6—H6A	0.9300
N1—N2	1.373 (2)	C7—C8	1.367 (3)
N1—C1	1.433 (3)	C7—C10	1.464 (3)
N2—N3	1.294 (3)	C8—C9	1.490 (3)
N3—C7	1.370 (2)	C9—H9A	0.9600
N4—C10	1.359 (3)	C9—H9B	0.9600
N4—N5	1.363 (2)	C9—H9C	0.9600
N4—H4	0.893 (10)	C11—C12	1.510 (3)
N5—C12	1.292 (3)	C12—C13	1.452 (3)
N6—C11	1.342 (3)	C13—C14	1.381 (3)
N6—C18	1.409 (3)	C13—C18	1.398 (3)
N6—H6	0.881 (10)	C14—C15	1.386 (3)
C1—C2	1.370 (3)	C14—H14	0.9300
C1—C6	1.382 (3)	C15—C16	1.381 (3)
C2—C3	1.384 (3)	C15—H15	0.9300
C2—H2	0.9300	C16—C17	1.386 (3)
C3—C4	1.366 (4)	C16—H16	0.9300
C3—H3	0.9300	C17—C18	1.370 (4)
C4—C5	1.362 (4)	C17—H17	0.9300
C4—H4A	0.9300
C8—N1—N2	110.09 (18)	C7—C8—C9	130.12 (19)
C8—N1—C1	131.86 (18)	C8—C9—H9A	109.5
N2—N1—C1	118.04 (16)	C8—C9—H9B	109.5
N3—N2—N1	107.84 (15)	H9A—C9—H9B	109.5
N2—N3—C7	108.50 (18)	C8—C9—H9C	109.5
C10—N4—N5	120.71 (17)	H9A—C9—H9C	109.5
C10—N4—H4	120.9 (17)	H9B—C9—H9C	109.5
N5—N4—H4	118.4 (17)	O1—C10—N4	123.7 (2)
C12—N5—N4	115.54 (17)	O1—C10—C7	123.0 (2)
C11—N6—C18	111.56 (17)	N4—C10—C7	113.29 (17)
C11—N6—H6	126 (2)	O2—C11—N6	127.5 (2)
C18—N6—H6	123 (2)	O2—C11—C12	126.4 (2)
C2—C1—C6	120.5 (2)	N6—C11—C12	106.15 (19)
C2—C1—N1	121.36 (19)	N5—C12—C13	127.19 (18)
C6—C1—N1	118.1 (2)	N5—C12—C11	126.6 (2)
C1—C2—C3	119.6 (2)	C13—C12—C11	106.22 (18)
C1—C2—H2	120.2	C14—C13—C18	119.9 (2)
C3—C2—H2	120.2	C14—C13—C12	133.57 (19)
C4—C3—C2	120.6 (3)	C18—C13—C12	106.52 (17)
C4—C3—H3	119.7	C13—C14—C15	118.6 (2)
C2—C3—H3	119.7	C13—C14—H14	120.7
C5—C4—C3	119.4 (3)	C15—C14—H14	120.7
C5—C4—H4A	120.3	C16—C15—C14	120.5 (2)
C3—C4—H4A	120.3	C16—C15—H15	119.8
C4—C5—C6	121.4 (2)	C14—C15—H15	119.8
C4—C5—H5	119.3	C15—C16—C17	121.6 (2)
C6—C5—H5	119.3	C15—C16—H16	119.2
C1—C6—C5	118.4 (3)	C17—C16—H16	119.2
C1—C6—H6A	120.8	C18—C17—C16	117.6 (2)
C5—C6—H6A	120.8	C18—C17—H17	121.2
C8—C7—N3	109.67 (19)	C16—C17—H17	121.2
C8—C7—C10	129.15 (18)	C17—C18—C13	121.8 (2)
N3—C7—C10	121.2 (2)	C17—C18—N6	128.7 (2)
N1—C8—C7	103.88 (17)	C13—C18—N6	109.5 (2)
N1—C8—C9	125.7 (2)
C8—N1—N2—N3	−0.7 (3)	N3—C7—C10—O1	174.1 (2)
C1—N1—N2—N3	178.00 (19)	C8—C7—C10—N4	175.3 (2)
N1—N2—N3—C7	−0.4 (2)	N3—C7—C10—N4	−6.3 (3)
C10—N4—N5—C12	174.1 (2)	C18—N6—C11—O2	−178.5 (2)
C8—N1—C1—C2	25.8 (4)	C18—N6—C11—C12	0.8 (3)
N2—N1—C1—C2	−152.5 (2)	N4—N5—C12—C13	178.4 (2)
C8—N1—C1—C6	−155.0 (2)	N4—N5—C12—C11	−0.9 (3)
N2—N1—C1—C6	26.7 (3)	O2—C11—C12—N5	−3.6 (4)
C6—C1—C2—C3	1.2 (4)	N6—C11—C12—N5	177.0 (2)
N1—C1—C2—C3	−179.6 (2)	O2—C11—C12—C13	176.9 (2)
C1—C2—C3—C4	−1.3 (4)	N6—C11—C12—C13	−2.4 (3)
C2—C3—C4—C5	0.3 (4)	N5—C12—C13—C14	5.4 (4)
C3—C4—C5—C6	0.7 (4)	C11—C12—C13—C14	−175.2 (2)
C2—C1—C6—C5	−0.2 (4)	N5—C12—C13—C18	−176.4 (2)
N1—C1—C6—C5	−179.4 (2)	C11—C12—C13—C18	3.1 (2)
C4—C5—C6—C1	−0.8 (4)	C18—C13—C14—C15	2.1 (3)
N2—N3—C7—C8	1.3 (3)	C12—C13—C14—C15	−179.9 (2)
N2—N3—C7—C10	−177.4 (2)	C13—C14—C15—C16	−0.1 (4)
N2—N1—C8—C7	1.4 (2)	C14—C15—C16—C17	−1.1 (4)
C1—N1—C8—C7	−177.0 (2)	C15—C16—C17—C18	0.3 (4)
N2—N1—C8—C9	−173.2 (2)	C16—C17—C18—C13	1.7 (4)
C1—N1—C8—C9	8.4 (4)	C16—C17—C18—N6	−176.8 (2)
N3—C7—C8—N1	−1.6 (2)	C14—C13—C18—C17	−2.9 (4)
C10—C7—C8—N1	176.9 (2)	C12—C13—C18—C17	178.5 (2)
N3—C7—C8—C9	172.6 (2)	C14—C13—C18—N6	175.9 (2)
C10—C7—C8—C9	−8.8 (4)	C12—C13—C18—N6	−2.7 (3)
N5—N4—C10—O1	−0.5 (4)	C11—N6—C18—C17	179.9 (3)
N5—N4—C10—C7	179.92 (19)	C11—N6—C18—C13	1.2 (3)
C8—C7—C10—O1	−4.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O2	0.89 (1)	1.95 (2)	2.685 (2)	138 (2)
N4—H4···N3	0.89 (1)	2.34 (2)	2.715 (3)	105 (2)
N6—H6···O1i	0.88 (1)	1.95 (2)	2.783 (2)	157 (3)
C14—H14···O2ii	0.93	2.33	3.244 (3)	168
C9—H9C···Cg1iii	0.96	2.94	3.822 (2)	154

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C13–C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯O2	0.89 (1)	1.95 (2)	2.685 (2)	138 (2)
N4—H4⋯N3	0.89 (1)	2.34 (2)	2.715 (3)	105 (2)
N6—H6⋯O1i	0.88 (1)	1.95 (2)	2.783 (2)	157 (3)
C14—H14⋯O2ii	0.93	2.33	3.244 (3)	168
C9—H9C⋯Cg1iii	0.96	2.94	3.822 (2)	154

Symmetry codes: (i) ; (ii) ; (iii) .