1-[(1-Benzyl-1H-1,2,3-triazol-4-yl)meth-yl]indoline-2,3-dione.

In the title compound, C18H14N4O2, the triazole ring makes dihedral angles of 77.32 (8) and 75.56 (9)°, respectively, with the indoline residue and the terminal phenyl group. In the crystal, mol-ecules are linked by C-H⋯N hydrogen bonds into tapes parallel to the b axis. The tapes are linked together by π-π inter-actions between triazole rings [inter--centroid distance = 3.4945 (9) Å].

Related literature

For the biological activity of indoline derivatives, see: Bhrigu et al. (2010 ▶); Da Silva et al. (2001 ▶); Ramachandran (2011 ▶); Smitha et al. (2008 ▶). For structures of indoline-2,3-dione derivatives, see: Qachchachi et al. (2013 ▶, 2014 ▶).

Experimental

Crystal data

C18H14N4O2

M = 318.33

Monoclinic,

a = 11.53860 (18) Å

b = 5.38700 (9) Å

c = 23.2433 (4) Å

β = 92.1048 (16)°

V = 1443.79 (4) Å3

Z = 4

Cu Kα radiation

μ = 0.81 mm−1

T = 123 K

0.20 × 0.04 × 0.02 mm

Data collection

Agilent SuperNova, Single source at offset, Atlas diffractometer

Absorption correction: multi-scan [CrysAlis PRO (Agilent, 2013 ▶), using expressions derived from Clark & Reid (1995 ▶)] T min = 0.722, T max = 1.000

11043 measured reflections

2882 independent reflections

2480 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.123

S = 1.04

2882 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis PRO (Agilent, 2013 ▶); 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 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814008423/bt6975sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814008423/bt6975Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814008423/bt6975Isup3.cml

CCDC reference: 997252

Additional supporting information: crystallographic information; 3D view; checkCIF report

C18H14N4O2	F(000) = 664
Mr = 318.33	Dx = 1.464 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 4927 reflections
a = 11.53860 (18) Å	θ = 3.8–73.3°
b = 5.38700 (9) Å	µ = 0.81 mm−1
c = 23.2433 (4) Å	T = 123 K
β = 92.1048 (16)°	Rod, clear intense yellow
V = 1443.79 (4) Å3	0.20 × 0.04 × 0.02 mm
Z = 4

Agilent SuperNova, Single source at offset, Atlas diffractometer	2882 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2480 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.032
Detector resolution: 10.3546 pixels mm-1	θmax = 73.5°, θmin = 3.8°
ω scans	h = −14→11
Absorption correction: multi-scan [CrysAlis PRO (Agilent, 2013), using expressions derived from Clark & Reid (1995)]	k = −6→6
Tmin = 0.722, Tmax = 1.000	l = −28→27
11043 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0677P)2 + 0.6175P] where P = (Fo2 + 2Fc2)/3
2882 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.22 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 > 2σ(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	0.65655 (11)	−0.1406 (2)	1.29231 (5)	0.0327 (3)
O2	0.48639 (10)	−0.1470 (2)	1.19284 (6)	0.0333 (3)
N1	0.59263 (12)	0.1979 (3)	1.16704 (6)	0.0258 (3)
N3	0.66397 (12)	−0.0542 (2)	0.99818 (6)	0.0267 (3)
N4	0.67538 (12)	0.1811 (3)	0.98001 (6)	0.0255 (3)
N2	0.61294 (12)	−0.0461 (3)	1.04795 (6)	0.0264 (3)
C9	0.52982 (14)	0.2675 (3)	1.11417 (7)	0.0269 (4)
H9A	0.5179	0.4457	1.1140	0.032*
H9B	0.4541	0.1888	1.1133	0.032*
C1	0.69237 (13)	0.3209 (3)	1.18873 (7)	0.0235 (3)
C2	0.74712 (14)	0.5253 (3)	1.16601 (7)	0.0253 (3)
H2	0.7192	0.6016	1.1324	0.030*
C4	0.88894 (14)	0.5000 (3)	1.24613 (7)	0.0287 (4)
H4	0.9552	0.5625	1.2649	0.034*
C10	0.59134 (13)	0.1956 (3)	1.06114 (7)	0.0242 (3)
C18	0.94153 (15)	0.2600 (3)	0.94699 (7)	0.0287 (4)
H18	0.9284	0.4072	0.9666	0.034*
C6	0.73451 (14)	0.2077 (3)	1.23951 (7)	0.0250 (3)
C5	0.83290 (14)	0.2949 (3)	1.26844 (7)	0.0276 (4)
H5	0.8610	0.2184	1.3020	0.033*
C13	0.84837 (15)	0.1331 (3)	0.92142 (7)	0.0267 (4)
C3	0.84634 (14)	0.6118 (3)	1.19591 (7)	0.0274 (4)
H3	0.8851	0.7488	1.1817	0.033*
C7	0.65586 (14)	0.0030 (3)	1.25238 (7)	0.0264 (4)
C12	0.72714 (15)	0.2352 (3)	0.92448 (7)	0.0293 (4)
H12A	0.7291	0.4135	0.9188	0.035*
H12B	0.6789	0.1639	0.8937	0.035*
C17	1.05397 (15)	0.1708 (4)	0.94380 (8)	0.0332 (4)
H17	1.1155	0.2578	0.9611	0.040*
C16	1.07402 (17)	−0.0482 (4)	0.91471 (8)	0.0356 (4)
H16	1.1491	−0.1094	0.9125	0.043*
C11	0.63147 (13)	0.3411 (3)	1.01791 (7)	0.0258 (3)
H11	0.6289	0.5133	1.0153	0.031*
C14	0.86952 (17)	−0.0866 (3)	0.89222 (7)	0.0327 (4)
H14	0.8082	−0.1740	0.8748	0.039*
C15	0.98220 (18)	−0.1757 (4)	0.88899 (8)	0.0376 (4)
H15	0.9958	−0.3225	0.8693	0.045*
C8	0.56440 (14)	0.0017 (3)	1.20128 (7)	0.0268 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0334 (6)	0.0294 (6)	0.0359 (7)	0.0032 (5)	0.0104 (5)	0.0061 (5)
O2	0.0274 (6)	0.0285 (6)	0.0444 (7)	−0.0058 (5)	0.0064 (5)	−0.0018 (5)
N1	0.0235 (6)	0.0253 (7)	0.0286 (7)	−0.0017 (5)	0.0023 (5)	−0.0016 (5)
N3	0.0303 (7)	0.0193 (7)	0.0307 (7)	−0.0013 (5)	0.0024 (6)	0.0006 (5)
N4	0.0250 (7)	0.0215 (7)	0.0300 (7)	−0.0017 (5)	−0.0001 (5)	0.0026 (5)
N2	0.0275 (7)	0.0220 (7)	0.0299 (7)	−0.0005 (5)	0.0026 (5)	0.0003 (5)
C9	0.0239 (7)	0.0259 (8)	0.0307 (8)	0.0012 (6)	0.0000 (6)	−0.0031 (6)
C1	0.0223 (7)	0.0236 (8)	0.0250 (7)	0.0021 (6)	0.0054 (6)	−0.0039 (6)
C2	0.0269 (8)	0.0234 (8)	0.0259 (8)	0.0001 (6)	0.0040 (6)	−0.0015 (6)
C4	0.0254 (8)	0.0318 (9)	0.0288 (8)	−0.0024 (7)	0.0018 (6)	−0.0049 (7)
C10	0.0201 (7)	0.0225 (8)	0.0298 (8)	0.0008 (6)	−0.0027 (6)	−0.0019 (6)
C18	0.0337 (9)	0.0257 (8)	0.0267 (8)	−0.0003 (7)	0.0032 (7)	−0.0006 (6)
C6	0.0256 (7)	0.0242 (8)	0.0256 (8)	0.0027 (6)	0.0076 (6)	−0.0017 (6)
C5	0.0270 (8)	0.0306 (8)	0.0255 (8)	0.0032 (6)	0.0039 (6)	−0.0014 (6)
C13	0.0323 (8)	0.0242 (8)	0.0238 (7)	−0.0008 (6)	0.0033 (6)	0.0061 (6)
C3	0.0267 (8)	0.0256 (8)	0.0303 (8)	−0.0030 (6)	0.0075 (6)	−0.0025 (6)
C7	0.0267 (8)	0.0219 (8)	0.0310 (8)	0.0030 (6)	0.0090 (6)	−0.0011 (6)
C12	0.0320 (8)	0.0292 (9)	0.0268 (8)	−0.0017 (7)	0.0010 (6)	0.0056 (7)
C17	0.0304 (9)	0.0377 (10)	0.0315 (9)	−0.0009 (7)	0.0032 (7)	0.0051 (7)
C16	0.0377 (9)	0.0379 (10)	0.0318 (9)	0.0098 (8)	0.0108 (7)	0.0092 (8)
C11	0.0239 (8)	0.0190 (7)	0.0343 (9)	0.0004 (6)	−0.0029 (6)	−0.0008 (6)
C14	0.0430 (10)	0.0266 (9)	0.0284 (8)	−0.0052 (7)	0.0022 (7)	0.0005 (7)
C15	0.0555 (12)	0.0277 (9)	0.0305 (9)	0.0063 (8)	0.0130 (8)	0.0023 (7)
C8	0.0238 (8)	0.0227 (8)	0.0343 (9)	0.0001 (6)	0.0081 (6)	−0.0024 (6)

O1—C7	1.208 (2)	C18—C17	1.388 (3)
O2—C8	1.216 (2)	C18—C13	1.389 (2)
N1—C8	1.370 (2)	C18—H18	0.9300
N1—C1	1.406 (2)	C6—C5	1.380 (2)
N1—C9	1.453 (2)	C6—C7	1.466 (2)
N3—N2	1.318 (2)	C5—H5	0.9300
N3—N4	1.3436 (19)	C13—C14	1.390 (2)
N4—C11	1.345 (2)	C13—C12	1.507 (2)
N4—C12	1.471 (2)	C3—H3	0.9300
N2—C10	1.362 (2)	C7—C8	1.560 (2)
C9—C10	1.496 (2)	C12—H12A	0.9700
C9—H9A	0.9700	C12—H12B	0.9700
C9—H9B	0.9700	C17—C16	1.383 (3)
C1—C2	1.384 (2)	C17—H17	0.9300
C1—C6	1.400 (2)	C16—C15	1.380 (3)
C2—C3	1.397 (2)	C16—H16	0.9300
C2—H2	0.9300	C11—H11	0.9300
C4—C3	1.387 (2)	C14—C15	1.391 (3)
C4—C5	1.390 (2)	C14—H14	0.9300
C4—H4	0.9300	C15—H15	0.9300
C10—C11	1.369 (2)
C8—N1—C1	111.37 (14)	C4—C5—H5	120.8
C8—N1—C9	124.67 (14)	C18—C13—C14	118.74 (16)
C1—N1—C9	123.94 (14)	C18—C13—C12	120.34 (16)
N2—N3—N4	107.26 (13)	C14—C13—C12	120.91 (16)
N3—N4—C11	110.80 (13)	C4—C3—C2	122.16 (16)
N3—N4—C12	120.69 (14)	C4—C3—H3	118.9
C11—N4—C12	128.48 (14)	C2—C3—H3	118.9
N3—N2—C10	108.69 (13)	O1—C7—C6	130.68 (17)
N1—C9—C10	113.14 (13)	O1—C7—C8	124.58 (15)
N1—C9—H9A	109.0	C6—C7—C8	104.74 (13)
C10—C9—H9A	109.0	N4—C12—C13	112.11 (13)
N1—C9—H9B	109.0	N4—C12—H12A	109.2
C10—C9—H9B	109.0	C13—C12—H12A	109.2
H9A—C9—H9B	107.8	N4—C12—H12B	109.2
C2—C1—C6	121.28 (15)	C13—C12—H12B	109.2
C2—C1—N1	128.14 (15)	H12A—C12—H12B	107.9
C6—C1—N1	110.58 (14)	C16—C17—C18	119.66 (18)
C1—C2—C3	116.92 (15)	C16—C17—H17	120.2
C1—C2—H2	121.5	C18—C17—H17	120.2
C3—C2—H2	121.5	C15—C16—C17	119.75 (17)
C3—C4—C5	120.24 (16)	C15—C16—H16	120.1
C3—C4—H4	119.9	C17—C16—H16	120.1
C5—C4—H4	119.9	N4—C11—C10	105.03 (14)
N2—C10—C11	108.21 (14)	N4—C11—H11	127.5
N2—C10—C9	121.95 (15)	C10—C11—H11	127.5
C11—C10—C9	129.80 (15)	C13—C14—C15	120.10 (17)
C17—C18—C13	121.12 (17)	C13—C14—H14	120.0
C17—C18—H18	119.4	C15—C14—H14	120.0
C13—C18—H18	119.4	C16—C15—C14	120.62 (17)
C5—C6—C1	121.09 (16)	C16—C15—H15	119.7
C5—C6—C7	131.36 (16)	C14—C15—H15	119.7
C1—C6—C7	107.54 (15)	O2—C8—N1	127.25 (16)
C6—C5—C4	118.32 (16)	O2—C8—C7	127.03 (16)
C6—C5—H5	120.8	N1—C8—C7	105.70 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···N2i	0.93	2.50	3.383 (2)	158
C11—H11···N3i	0.93	2.40	3.313 (2)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯N2i	0.93	2.50	3.383 (2)	158
C11—H11⋯N3i	0.93	2.40	3.313 (2)	167

Symmetry code: (i) .