5-Methyl-N′-[(3Z)-2-oxo-2,3-dihydro-1H-indol-3-yl­idene]-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide

Mohamed, H.A.; Abdel-Wahab, B.F.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536813007502

organic compounds

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ISSN: 2056-9890

Volume 69| Part 4| April 2013| Page o577

doi:10.1107/S1600536813007502

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5-Methyl-N′-[(3Z)-2-oxo-2,3-dihydro-1H-indol-3-ylidene]-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide

Hanan A. Mohamed,^a Bakr F. Abdel-Wahab,^a ‡ Seik Weng Ng ^b,^c and Edward R. T. Tiekink ^b ^*

^aApplied Organic Chemistry Department, National Research Centre, Dokki, 12622 Giza, Egypt, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 18 March 2013; accepted 18 March 2013; online 23 March 2013)

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 intramolecular bifurcated N—H⋯(O,N) hydrogen bond. The conformation about the N=C bond is Z. In the crystal, supramolecular chains along [101] are sustained by N—H⋯O hydrogen bonds and C—H⋯O interactions. These are consolidated into a three-dimensional architecture by C—H⋯π and π–π interactions; 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_r = 346.35
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.058
wR(F²) = 0.147
S = 1.03
3715 reflections
244 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.20 e Å⁻³

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) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813007502/hb7059sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536813007502/hb7059Isup3.cml

checkCIF report

Comment top

The title compound (I) was investigated in relation to the established biological activities exhibited by 1,2,3-triazoles (Abdel-Wahab et al., 2012; Jordão et al., 2011).

With respect to the 1,2,3-triazole ring (r.m.s. deviation = 0.010 Å) in (I), Fig. 1, both the benzene [dihedral angle = 26.20 (13)°] and to a lesser extent the amide residues are twisted [C10—C7—C8—C9 torsion angle = -8.8 (4)°]. The nine non-hydrogen ring atoms of the 3-imino-1H-indol-2-one residue are co-planar, having a r.m.s. deviation of 0.032 Å. The formation of intramolecular N4—H···O2 and N4—H···N3 hydrogen bonds, Table 1, confers stability to the co-planar arrangement in the central region of the molecule, i.e. the N4—N5—C12—C11 and N3—C7—C10—N4 torsion angles are -0.9 (3) and -6.3 (3)°, respectively. Finally, the conformation about the N5═C12 bond is Z.

Supramolecular chains propagating along [1 0 1] feature in the crystal packing. These are sustained by N6—H···O1 hydrogen bonds and supported by C14—H···O2 interactions, Table 1, and lead to 12-membered {···OCN₂C₃H···OCNH} synthons, Fig. 2. The chains assemble in layers parallel to (1 0 1) and are connected into the three-dimensional architecture by C—H···π interactions between a methyl-H and the C13–C18 benzene ring, Table 1, and π—π interactions between centrosymmetrically related 1,2,3-triazole rings [inter-centroid distance = 3.6056 (14) Å for symmetry operation 1 - x, 1 - y, 1 - z], Fig. 3.

Related literature top

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

Experimental top

A mixture of 5-methyl-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide (0.22 g, 0.001 M) and indoline-2,3-dione (0.15 g, 0.001 M) in anhydrous ethanol (30 ml) in the presence of a catalytic amount of glacial acetic acid was heated under reflux for about 4 h. The resultant solid was filtered and dried. Re-crystallization was by slow evaporation of its DMF solution which yielded yellow prisms in 73% yield; M.pt: 562–564 K.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); 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).

Figures top

	Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 35% probability level.
	Fig. 2. A view of the supramolecular chain along [1 0 1] sustained by N—H···O and C—H···O interactions, shown as blue and orange dashed lines, respectively.
	Fig. 3. A view of the crystal packing in projection down the b axis. The N—H···O, C—H···π and π—π interactions are shown as blue, brown and purple dashed lines, respectively.

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

Crystal data top

C₁₈H₁₄N₆O₂	F(000) = 720
M_r = 346.35	D_x = 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

Data collection top

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	R_int = 0.039
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 3.0°
ω scan	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −21→24
T_min = 0.971, T_max = 1.000	l = −15→16
8876 measured reflections

Refinement top

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(F_o²) + (0.0482P)² + 0.2228P] where P = (F_o² + 2F_c²)/3
3715 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.16 e Å⁻³
2 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₈H₁₄N₆O₂	V = 1610.5 (3) Å³
M_r = 346.35	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.1835 (8) Å	µ = 0.10 mm⁻¹
b = 18.620 (2) Å	T = 295 K
c = 12.2949 (11) Å	0.25 × 0.05 × 0.05 mm
β = 101.676 (11)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3715 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2131 reflections with I > 2σ(I)
T_min = 0.971, T_max = 1.000	R_int = 0.039
8876 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	2 restraints
wR(F²) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.16 e Å⁻³
3715 reflections	Δρ_min = −0.20 e Å⁻³
244 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1/2, −y+3/2, z+1/2; (ii) x−1/2, −y+3/2, z−1/2; (iii) −x+3/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₄N₆O₂
M_r	346.35
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	7.1835 (8), 18.620 (2), 12.2949 (11)
β (°)	101.676 (11)
V (Å³)	1610.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.25 × 0.05 × 0.05

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.971, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8876, 3715, 2131
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.147, 1.03
No. of reflections	3715
No. of parameters	244
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.20

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C13–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O2	0.893 (10)	1.951 (18)	2.685 (2)	138 (2)
N4—H4···N3	0.893 (10)	2.34 (2)	2.715 (3)	105.4 (18)
N6—H6···O1ⁱ	0.881 (10)	1.949 (15)	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) x+1/2, −y+3/2, z+1/2; (ii) x−1/2, −y+3/2, z−1/2; (iii) −x+3/2, y−1/2, −z+1/2.

Footnotes

‡Additional correspondence author, e-mail: bakrfatehy@yahoo.com.

Acknowledgements

We thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/03).

References

Abdel-Wahab, B. F., Abdel-Latif, E., Mohamed, H. A. & Awad, G. E. A. (2012). Eur. J. Med. Chem. 52, 263–268. Web of Science CAS PubMed Google Scholar
Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Jordão, A. K., Ferreira, V. F., Souza, T. M., Faria, G. G., Machado, V., Abrantes, J. L., de Souza, M. C. & Cunha, A. C. (2011). Bioorg. Med. Chem. 19, 1860–1865. Web of Science PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 69| Part 4| April 2013| Page o577

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

5-Methyl-N′-[(3Z)-2-oxo-2,3-di­hydro-1H-indol-3-yl­­idene]-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

5-Methyl-N′-[(3Z)-2-oxo-2,3-dihydro-1H-indol-3-ylidene]-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide