Ethyl 3-{[(3-methyl-anilino)(1H-1,2,4-triazol-1-yl)methyl-idene]amino}-1-benzofuran-2-carboxyl-ate.

The crystal structure of the title compound, C(21)H(19)N(5)O(3), is stabilized by inter-molecular N-H⋯N and C-H⋯O hydrogen bonds. The mol-ecule contains a planar [maximum deviations = -0.026 (1) and 0.027 (2) Å] benzofuran ring system, which forms dihedral angles of 78.75 (8) and 39.78 (7)° with the benzene and triazole rings, respectively.

Related literature

For the synthesis of heterocyclic compounds, see: Hu et al. (2007 ▶); Hu & Ding (2008 ▶). For related structures, see: Hu et al. (2010 ▶); Chen et al. (2008 ▶); Ma et al. (2009 ▶); Yang et al. (2009 ▶).

Experimental

Crystal data

C21H19N5O3

M = 389.41

Monoclinic,

a = 10.967 (1) Å

b = 9.9606 (9) Å

c = 17.4807 (15) Å

β = 91.439 (1)°

V = 1909.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.972, T max = 0.991

14116 measured reflections

4713 independent reflections

3715 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.135

S = 1.07

4713 reflections

267 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810042868/jh2221sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042868/jh2221Isup2.hkl

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

C21H19N5O3	F(000) = 816
Mr = 389.41	Dx = 1.355 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4199 reflections
a = 10.967 (1) Å	θ = 2.2–25.7°
b = 9.9606 (9) Å	µ = 0.09 mm−1
c = 17.4807 (15) Å	T = 298 K
β = 91.439 (1)°	Block, colorless
V = 1909.0 (3) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Bruker SMART 4K CCD area-detector diffractometer	4713 independent reflections
Radiation source: fine-focus sealed tube	3715 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −14→14
Tmin = 0.972, Tmax = 0.991	k = −13→12
14116 measured reflections	l = −23→22

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0611P)2 + 0.263P] where P = (Fo2 + 2Fc2)/3
4713 reflections	(Δ/σ)max = 0.001
267 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.23 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
C1	−0.0436 (2)	0.3180 (2)	1.13054 (12)	0.0700 (6)
H1A	−0.0632	0.2688	1.1758	0.105*
H1B	−0.1172	0.3376	1.1018	0.105*
H1C	−0.0036	0.4003	1.1447	0.105*
C2	0.03957 (14)	0.23527 (18)	1.08246 (9)	0.0430 (4)
C3	0.09144 (14)	0.29052 (16)	1.01810 (8)	0.0365 (3)
H3	0.0738	0.3790	1.0049	0.044*
C4	0.16873 (13)	0.21673 (15)	0.97313 (8)	0.0322 (3)
C5	0.19517 (16)	0.08510 (16)	0.99188 (9)	0.0448 (4)
H5	0.2485	0.0354	0.9626	0.054*
C6	0.14145 (18)	0.02809 (19)	1.05469 (11)	0.0558 (5)
H6	0.1573	−0.0612	1.0670	0.067*
C7	0.06476 (16)	0.10228 (19)	1.09921 (10)	0.0517 (5)
H7	0.0293	0.0624	1.1413	0.062*
C8	0.26228 (13)	0.39756 (14)	0.89881 (8)	0.0305 (3)
C9	0.32102 (15)	0.54488 (16)	0.78959 (9)	0.0404 (4)
H9	0.3687	0.6067	0.8167	0.048*
C10	0.22640 (19)	0.44048 (17)	0.70420 (9)	0.0514 (5)
H10	0.1958	0.4171	0.6559	0.062*
C11	0.32117 (14)	0.45550 (15)	1.02485 (8)	0.0338 (3)
C12	0.39857 (14)	0.36751 (16)	1.06072 (8)	0.0390 (4)
C13	0.30913 (16)	0.47691 (17)	1.15284 (9)	0.0441 (4)
C14	0.26388 (15)	0.53020 (16)	1.08480 (8)	0.0387 (4)
C15	0.17586 (17)	0.63069 (17)	1.08694 (10)	0.0483 (4)
H15	0.1442	0.6684	1.0420	0.058*
C16	0.1368 (2)	0.6728 (2)	1.15721 (12)	0.0628 (5)
H16	0.0776	0.7394	1.1596	0.075*
C17	0.1844 (2)	0.6175 (2)	1.22463 (12)	0.0690 (6)
H17	0.1569	0.6487	1.2713	0.083*
C18	0.2710 (2)	0.5180 (2)	1.22393 (10)	0.0611 (5)
H18	0.3024	0.4802	1.2689	0.073*
C19	0.48201 (16)	0.26505 (17)	1.03424 (10)	0.0455 (4)
C20	0.55170 (19)	0.1573 (2)	0.92310 (13)	0.0646 (6)
H20A	0.5239	0.0695	0.9391	0.077*
H20B	0.6372	0.1666	0.9377	0.077*
C21	0.5346 (2)	0.1731 (2)	0.83896 (14)	0.0776 (7)
H21A	0.4493	0.1680	0.8256	0.116*
H21B	0.5774	0.1028	0.8133	0.116*
H21C	0.5660	0.2587	0.8236	0.116*
N1	0.21649 (12)	0.27264 (13)	0.90558 (7)	0.0353 (3)
H1	0.2075 (15)	0.2264 (16)	0.8641 (10)	0.042*
N2	0.30167 (12)	0.48370 (12)	0.94727 (7)	0.0344 (3)
N3	0.26523 (11)	0.43926 (12)	0.82068 (7)	0.0333 (3)
N4	0.20199 (15)	0.37086 (14)	0.76506 (7)	0.0493 (4)
N5	0.29902 (14)	0.54902 (14)	0.71559 (7)	0.0480 (4)
O1	0.48087 (11)	0.26108 (12)	0.95828 (7)	0.0489 (3)
O2	0.54273 (14)	0.19350 (14)	1.07513 (8)	0.0728 (4)
O3	0.39307 (11)	0.37876 (12)	1.13978 (6)	0.0483 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0739 (14)	0.0835 (15)	0.0539 (12)	0.0117 (12)	0.0255 (11)	0.0014 (11)
C2	0.0384 (8)	0.0575 (10)	0.0330 (8)	−0.0004 (7)	0.0014 (7)	0.0014 (7)
C3	0.0376 (8)	0.0376 (8)	0.0342 (8)	0.0000 (6)	−0.0007 (6)	0.0019 (6)
C4	0.0355 (7)	0.0366 (8)	0.0244 (7)	−0.0050 (6)	−0.0027 (6)	0.0015 (6)
C5	0.0550 (10)	0.0399 (9)	0.0396 (9)	0.0056 (8)	0.0063 (7)	0.0032 (7)
C6	0.0690 (12)	0.0441 (10)	0.0545 (11)	0.0053 (9)	0.0079 (9)	0.0184 (8)
C7	0.0506 (10)	0.0657 (12)	0.0391 (9)	−0.0011 (9)	0.0075 (8)	0.0184 (9)
C8	0.0350 (7)	0.0313 (7)	0.0251 (7)	0.0066 (6)	0.0005 (5)	0.0022 (6)
C9	0.0506 (9)	0.0391 (8)	0.0315 (8)	−0.0036 (7)	0.0015 (7)	0.0032 (6)
C10	0.0851 (13)	0.0421 (9)	0.0266 (8)	−0.0038 (9)	−0.0074 (8)	0.0010 (7)
C11	0.0397 (8)	0.0327 (7)	0.0288 (7)	−0.0079 (6)	−0.0026 (6)	0.0006 (6)
C12	0.0433 (8)	0.0432 (9)	0.0299 (8)	−0.0055 (7)	−0.0073 (6)	0.0053 (6)
C13	0.0548 (10)	0.0458 (9)	0.0314 (8)	−0.0127 (8)	−0.0031 (7)	−0.0007 (7)
C14	0.0484 (9)	0.0384 (8)	0.0293 (8)	−0.0109 (7)	−0.0002 (6)	−0.0039 (6)
C15	0.0562 (10)	0.0441 (9)	0.0446 (10)	−0.0039 (8)	0.0026 (8)	−0.0078 (8)
C16	0.0748 (14)	0.0521 (11)	0.0622 (13)	−0.0078 (10)	0.0193 (11)	−0.0165 (10)
C17	0.1013 (17)	0.0632 (13)	0.0436 (11)	−0.0217 (13)	0.0244 (11)	−0.0197 (10)
C18	0.0886 (15)	0.0665 (13)	0.0284 (9)	−0.0230 (12)	0.0022 (9)	−0.0039 (8)
C19	0.0460 (9)	0.0422 (9)	0.0476 (10)	−0.0026 (7)	−0.0100 (7)	0.0091 (8)
C20	0.0551 (11)	0.0507 (11)	0.0885 (16)	0.0111 (9)	0.0140 (11)	−0.0061 (11)
C21	0.0790 (15)	0.0770 (15)	0.0782 (16)	−0.0006 (12)	0.0305 (12)	−0.0226 (13)
N1	0.0470 (7)	0.0353 (7)	0.0236 (6)	−0.0040 (6)	0.0019 (5)	−0.0024 (5)
N2	0.0454 (7)	0.0323 (6)	0.0254 (6)	0.0009 (5)	−0.0027 (5)	0.0007 (5)
N3	0.0436 (7)	0.0317 (6)	0.0245 (6)	0.0020 (5)	−0.0015 (5)	0.0006 (5)
N4	0.0785 (10)	0.0414 (8)	0.0276 (7)	−0.0099 (7)	−0.0090 (7)	0.0008 (6)
N5	0.0713 (10)	0.0438 (8)	0.0289 (7)	−0.0030 (7)	0.0017 (6)	0.0047 (6)
O1	0.0483 (7)	0.0495 (7)	0.0489 (7)	0.0125 (5)	0.0013 (5)	0.0001 (6)
O2	0.0816 (10)	0.0638 (9)	0.0719 (10)	0.0232 (8)	−0.0223 (8)	0.0150 (7)
O3	0.0609 (7)	0.0542 (7)	0.0291 (6)	−0.0065 (6)	−0.0107 (5)	0.0067 (5)

C1—C2	1.502 (3)	C11—C14	1.442 (2)
C1—H1A	0.9600	C12—O3	1.3895 (18)
C1—H1B	0.9600	C12—C19	1.454 (2)
C1—H1C	0.9600	C13—O3	1.366 (2)
C2—C7	1.383 (2)	C13—C14	1.383 (2)
C2—C3	1.387 (2)	C13—C18	1.383 (2)
C3—C4	1.382 (2)	C14—C15	1.392 (2)
C3—H3	0.9300	C15—C16	1.377 (2)
C4—C5	1.381 (2)	C15—H15	0.9300
C4—N1	1.4177 (18)	C16—C17	1.391 (3)
C5—C6	1.381 (2)	C16—H16	0.9300
C5—H5	0.9300	C17—C18	1.373 (3)
C6—C7	1.376 (3)	C17—H17	0.9300
C6—H6	0.9300	C18—H18	0.9300
C7—H7	0.9300	C19—O2	1.1993 (19)
C8—N2	1.2735 (18)	C19—O1	1.328 (2)
C8—N1	1.3481 (19)	C20—O1	1.440 (2)
C8—N3	1.4287 (17)	C20—C21	1.486 (3)
C9—N5	1.3105 (19)	C20—H20A	0.9700
C9—N3	1.3391 (19)	C20—H20B	0.9700
C9—H9	0.9300	C21—H21A	0.9600
C10—N4	1.303 (2)	C21—H21B	0.9600
C10—N5	1.354 (2)	C21—H21C	0.9600
C10—H10	0.9300	N1—H1	0.862 (17)
C11—C12	1.362 (2)	N3—N4	1.3626 (17)
C11—N2	1.3962 (18)
C2—C1—H1A	109.5	C13—C14—C15	119.15 (15)
C2—C1—H1B	109.5	C13—C14—C11	105.87 (15)
H1A—C1—H1B	109.5	C15—C14—C11	134.89 (15)
C2—C1—H1C	109.5	C16—C15—C14	118.35 (18)
H1A—C1—H1C	109.5	C16—C15—H15	120.8
H1B—C1—H1C	109.5	C14—C15—H15	120.8
C7—C2—C3	117.90 (16)	C15—C16—C17	121.1 (2)
C7—C2—C1	121.85 (16)	C15—C16—H16	119.4
C3—C2—C1	120.23 (16)	C17—C16—H16	119.4
C4—C3—C2	121.35 (15)	C18—C17—C16	121.55 (18)
C4—C3—H3	119.3	C18—C17—H17	119.2
C2—C3—H3	119.3	C16—C17—H17	119.2
C5—C4—C3	119.88 (14)	C17—C18—C13	116.53 (18)
C5—C4—N1	119.40 (14)	C17—C18—H18	121.7
C3—C4—N1	120.64 (13)	C13—C18—H18	121.7
C4—C5—C6	119.21 (16)	O2—C19—O1	124.70 (18)
C4—C5—H5	120.4	O2—C19—C12	124.88 (17)
C6—C5—H5	120.4	O1—C19—C12	110.42 (13)
C7—C6—C5	120.53 (17)	O1—C20—C21	106.89 (16)
C7—C6—H6	119.7	O1—C20—H20A	110.3
C5—C6—H6	119.7	C21—C20—H20A	110.3
C6—C7—C2	121.10 (16)	O1—C20—H20B	110.3
C6—C7—H7	119.5	C21—C20—H20B	110.3
C2—C7—H7	119.5	H20A—C20—H20B	108.6
N2—C8—N1	133.19 (13)	C20—C21—H21A	109.5
N2—C8—N3	115.11 (13)	C20—C21—H21B	109.5
N1—C8—N3	111.70 (12)	H21A—C21—H21B	109.5
N5—C9—N3	110.52 (14)	C20—C21—H21C	109.5
N5—C9—H9	124.7	H21A—C21—H21C	109.5
N3—C9—H9	124.7	H21B—C21—H21C	109.5
N4—C10—N5	115.89 (15)	C8—N1—C4	125.58 (12)
N4—C10—H10	122.1	C8—N1—H1	117.1 (11)
N5—C10—H10	122.1	C4—N1—H1	116.9 (11)
C12—C11—N2	130.93 (14)	C8—N2—C11	123.48 (12)
C12—C11—C14	105.98 (13)	C9—N3—N4	109.44 (12)
N2—C11—C14	122.90 (14)	C9—N3—C8	129.64 (13)
C11—C12—O3	111.34 (14)	N4—N3—C8	120.89 (12)
C11—C12—C19	134.03 (15)	C10—N4—N3	101.83 (13)
O3—C12—C19	114.62 (13)	C9—N5—C10	102.30 (13)
O3—C13—C14	111.09 (14)	C19—O1—C20	117.17 (14)
O3—C13—C18	125.62 (16)	C13—O3—C12	105.68 (12)
C14—C13—C18	123.29 (18)
C7—C2—C3—C4	−1.8 (2)	O3—C12—C19—O2	0.2 (2)
C1—C2—C3—C4	179.70 (16)	C11—C12—C19—O1	1.1 (3)
C2—C3—C4—C5	0.3 (2)	O3—C12—C19—O1	179.71 (13)
C2—C3—C4—N1	177.05 (13)	N2—C8—N1—C4	18.8 (3)
C3—C4—C5—C6	1.4 (2)	N3—C8—N1—C4	−160.66 (13)
N1—C4—C5—C6	−175.39 (15)	C5—C4—N1—C8	−139.07 (16)
C4—C5—C6—C7	−1.5 (3)	C3—C4—N1—C8	44.1 (2)
C5—C6—C7—C2	−0.1 (3)	N1—C8—N2—C11	9.3 (3)
C3—C2—C7—C6	1.7 (3)	N3—C8—N2—C11	−171.20 (13)
C1—C2—C7—C6	−179.82 (18)	C12—C11—N2—C8	62.4 (2)
N2—C11—C12—O3	176.20 (14)	C14—C11—N2—C8	−123.30 (16)
C14—C11—C12—O3	1.20 (17)	N5—C9—N3—N4	−0.78 (19)
N2—C11—C12—C19	−5.2 (3)	N5—C9—N3—C8	−178.69 (14)
C14—C11—C12—C19	179.85 (17)	N2—C8—N3—C9	12.4 (2)
O3—C13—C14—C15	179.20 (14)	N1—C8—N3—C9	−168.00 (15)
C18—C13—C14—C15	0.3 (3)	N2—C8—N3—N4	−165.31 (14)
O3—C13—C14—C11	2.24 (18)	N1—C8—N3—N4	14.28 (19)
C18—C13—C14—C11	−176.69 (16)	N5—C10—N4—N3	−0.7 (2)
C12—C11—C14—C13	−2.05 (17)	C9—N3—N4—C10	0.83 (18)
N2—C11—C14—C13	−177.55 (14)	C8—N3—N4—C10	178.97 (14)
C12—C11—C14—C15	−178.31 (18)	N3—C9—N5—C10	0.34 (19)
N2—C11—C14—C15	6.2 (3)	N4—C10—N5—C9	0.2 (2)
C13—C14—C15—C16	−0.3 (2)	O2—C19—O1—C20	4.3 (3)
C11—C14—C15—C16	175.60 (17)	C12—C19—O1—C20	−175.22 (14)
C14—C15—C16—C17	0.5 (3)	C21—C20—O1—C19	179.39 (16)
C15—C16—C17—C18	−0.7 (3)	C14—C13—O3—C12	−1.52 (17)
C16—C17—C18—C13	0.7 (3)	C18—C13—O3—C12	177.38 (16)
O3—C13—C18—C17	−179.23 (16)	C11—C12—O3—C13	0.14 (17)
C14—C13—C18—C17	−0.5 (3)	C19—C12—O3—C13	−178.79 (13)
C11—C12—C19—O2	−178.42 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2i	0.93	2.43	3.271 (2)	150
N1—H1···N5ii	0.862 (17)	2.250 (17)	3.0755 (19)	160.3 (15)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O2i	0.93	2.43	3.271 (2)	150
N1—H1⋯N5ii	0.862 (17)	2.250 (17)	3.0755 (19)	160.3 (15)

Symmetry codes: (i) ; (ii) .