Ethyl 3-{[(3-methyl­anilino)(1H-1,2,4-triazol-1-yl)methyl­idene]amino}-1-benzofuran-2-carboxyl­ate

Gao, H.-T.; Li, L.; Ma, J.-K.

doi:10.1107/S1600536810042868

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2966

https://doi.org/10.1107/S1600536810042868

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Ethyl 3-{[(3-methylanilino)(1H-1,2,4-triazol-1-yl)methylidene]amino}-1-benzofuran-2-carboxylate

Hai-Tao Gao,^a Li Li ^b and Jun-Kai Ma ^a ^*

^aInstitute of Medicinal Chemistry, Hubei Medical University, Shiyan Hubei 442000, People's Republic of China, and ^bHubei Medical University Library, Shiyan Hubei 442000, People's Republic of China
^*Correspondence e-mail: jkma6686@yahoo.com.cn

(Received 13 October 2010; accepted 21 October 2010; online 30 October 2010)

The crystal structure of the title compound, C₂₁H₁₉N₅O₃, is stabilized by intermolecular N—H⋯N and C—H⋯O hydrogen bonds. The molecule 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_r = 389.41
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.054
wR(F²) = 0.135
S = 1.07
4713 reflections
267 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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

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).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810042868/jh2221Isup2.hkl

checkCIF report

Comment top

As a part of our ongoing investigations on the preparation of derivatives of heterocyclic compounds (Hu et al., 2007, 2008, 2010; Chen et al., 2008; Ma et al., 2009; Yang et al., 2009), we have synthesized and structurally characterized characterized the title compound. Here we wish to report an x-ray crystal structure of it(Fig. 1). In the molecule, the mean plane of the benzofuran system make dihedral angle of 78.75 (8)°, 39.78 (7)°, with the phenyl(C2—C7) ring and the triazole ring, respectively. The crystal structure is mainly stabilized by weak intermolecular N—H···N and C—H···O hydrogen bonding interactions (Table. 1). There are no π-π interactions.

Related literature top

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

Experimental top

The title compound was obtained in excellent yield via aza-WIttig reaction. Crystals suitable for single-crystal X-ray diffraction were obtained by recrystallization from a mixed solvent of ethanol and dichloromethane (1:1 v/v) at room temperature.

Structure description top

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

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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).

Figures top

Fig. 1. The molecular structure of the title compound, showing the atom-labeling scheme.

Ethyl 3-{[(3-methylanilino)(1H-1,2,4-triazol-1-yl)methylidene]amino}- 1-benzofuran-2-carboxylate top

Crystal data top

C₂₁H₁₉N₅O₃	F(000) = 816
M_r = 389.41	D_x = 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

Data collection top

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

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)] = 0.054	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(F_o²) + (0.0611P)² + 0.263P] where P = (F_o² + 2F_c²)/3
4713 reflections	(Δ/σ)_max = 0.001
267 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₁H₁₉N₅O₃	V = 1909.0 (3) Å³
M_r = 389.41	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.967 (1) Å	µ = 0.09 mm⁻¹
b = 9.9606 (9) Å	T = 298 K
c = 17.4807 (15) Å	0.30 × 0.20 × 0.10 mm
β = 91.439 (1)°

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	4713 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	3715 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.991	R_int = 0.031
14116 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.26 e Å⁻³
4713 reflections	Δρ_min = −0.23 e Å⁻³
267 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
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₉N₅O₃
M_r	389.41
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	10.967 (1), 9.9606 (9), 17.4807 (15)
β (°)	91.439 (1)
V (Å³)	1909.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART 4K CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.972, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	14116, 4713, 3715
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.135, 1.07
No. of reflections	4713
No. of parameters	267
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.23

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2ⁱ	0.93	2.43	3.271 (2)	150.3
N1—H1···N5ⁱⁱ	0.862 (17)	2.250 (17)	3.0755 (19)	160.3 (15)

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) −x+1/2, y−1/2, −z+3/2.

Acknowledgements

We gratefully acknowledge financial support of this work by the Science Research Project of Hubei Medical University (Nos. 2008CXG01 and 2009QDJ22).

References

Bruker (2001). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, X.-B., Sun, F.-M., Gao, H.-T., Xu, J. & Zheng, A.-H. (2008). Acta Cryst. E64, o2352. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hu, Y. G. & Ding, M. W. (2008). Chin. J. Struct. Chem. 27, 21–24. Google Scholar
Hu, Y.-G., Hu, J. & Gao, H.-T. (2007). Acta Cryst. E63, o4735. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hu, Y.-G., Wang, Y., Du, S.-M., Chen, X.-B. & Ding, M.-W. (2010). Bioorg. Med. Chem. Lett. 20, 6188–6190. Web of Science CSD CrossRef CAS PubMed Google Scholar
Ma, J.-K., He, M. & Hu, Y.-G. (2009). Acta Cryst. E65, o2629. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, H.-Z., Gao, H.-T. & Ynag, X.-H. (2009). Acta Cryst. E65, o59–o60. Web of Science CSD CrossRef IUCr Journals Google Scholar

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

Ethyl 3-{[(3-methyl­anilino)(1H-1,2,4-triazol-1-yl)methyl­­idene]amino}-1-benzo­furan-2-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Ethyl 3-{[(3-methylanilino)(1H-1,2,4-triazol-1-yl)methylidene]amino}-1-benzofuran-2-carboxylate