PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2966.
Published online 2010 October 30. doi:  10.1107/S1600536810042868
PMCID: PMC3008986

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

Abstract

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 [triangle]); Hu & Ding (2008 [triangle]). For related structures, see: Hu et al. (2010 [triangle]); Chen et al. (2008 [triangle]); Ma et al. (2009 [triangle]); Yang et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2966-scheme1.jpg

Experimental

Crystal data

  • C21H19N5O3
  • M r = 389.41
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2966-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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.

Refinement

All H-atoms were positioned with idealized geometry and refined isotropic (Uiso(H)= 1.5Ueq(C)for methyl H atoms and Uiso(H) =1.2Ueq(C) for all other H atoms) using a riding model with C—H = 0.93°, 0.97°, 0.96Å and N—H = 0.86°.

Figures

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

Crystal data

C21H19N5O3F(000) = 816
Mr = 389.41Dx = 1.355 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4199 reflections
a = 10.967 (1) Åθ = 2.2–25.7°
b = 9.9606 (9) ŵ = 0.09 mm1
c = 17.4807 (15) ÅT = 298 K
β = 91.439 (1)°Block, colorless
V = 1909.0 (3) Å30.30 × 0.20 × 0.10 mm
Z = 4

Data collection

Bruker SMART 4K CCD area-detector diffractometer4713 independent reflections
Radiation source: fine-focus sealed tube3715 reflections with I > 2σ(I)
graphiteRint = 0.031
[var phi] and ω scansθmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)h = −14→14
Tmin = 0.972, Tmax = 0.991k = −13→12
14116 measured reflectionsl = −23→22

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H atoms treated by a mixture of independent and constrained refinement
S = 1.07w = 1/[σ2(Fo2) + (0.0611P)2 + 0.263P] where P = (Fo2 + 2Fc2)/3
4713 reflections(Δ/σ)max = 0.001
267 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = −0.23 e Å3

Special details

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)

xyzUiso*/Ueq
C1−0.0436 (2)0.3180 (2)1.13054 (12)0.0700 (6)
H1A−0.06320.26881.17580.105*
H1B−0.11720.33761.10180.105*
H1C−0.00360.40031.14470.105*
C20.03957 (14)0.23527 (18)1.08246 (9)0.0430 (4)
C30.09144 (14)0.29052 (16)1.01810 (8)0.0365 (3)
H30.07380.37901.00490.044*
C40.16873 (13)0.21673 (15)0.97313 (8)0.0322 (3)
C50.19517 (16)0.08510 (16)0.99188 (9)0.0448 (4)
H50.24850.03540.96260.054*
C60.14145 (18)0.02809 (19)1.05469 (11)0.0558 (5)
H60.1573−0.06121.06700.067*
C70.06476 (16)0.10228 (19)1.09921 (10)0.0517 (5)
H70.02930.06241.14130.062*
C80.26228 (13)0.39756 (14)0.89881 (8)0.0305 (3)
C90.32102 (15)0.54488 (16)0.78959 (9)0.0404 (4)
H90.36870.60670.81670.048*
C100.22640 (19)0.44048 (17)0.70420 (9)0.0514 (5)
H100.19580.41710.65590.062*
C110.32117 (14)0.45550 (15)1.02485 (8)0.0338 (3)
C120.39857 (14)0.36751 (16)1.06072 (8)0.0390 (4)
C130.30913 (16)0.47691 (17)1.15284 (9)0.0441 (4)
C140.26388 (15)0.53020 (16)1.08480 (8)0.0387 (4)
C150.17586 (17)0.63069 (17)1.08694 (10)0.0483 (4)
H150.14420.66841.04200.058*
C160.1368 (2)0.6728 (2)1.15721 (12)0.0628 (5)
H160.07760.73941.15960.075*
C170.1844 (2)0.6175 (2)1.22463 (12)0.0690 (6)
H170.15690.64871.27130.083*
C180.2710 (2)0.5180 (2)1.22393 (10)0.0611 (5)
H180.30240.48021.26890.073*
C190.48201 (16)0.26505 (17)1.03424 (10)0.0455 (4)
C200.55170 (19)0.1573 (2)0.92310 (13)0.0646 (6)
H20A0.52390.06950.93910.077*
H20B0.63720.16660.93770.077*
C210.5346 (2)0.1731 (2)0.83896 (14)0.0776 (7)
H21A0.44930.16800.82560.116*
H21B0.57740.10280.81330.116*
H21C0.56600.25870.82360.116*
N10.21649 (12)0.27264 (13)0.90558 (7)0.0353 (3)
H10.2075 (15)0.2264 (16)0.8641 (10)0.042*
N20.30167 (12)0.48370 (12)0.94727 (7)0.0344 (3)
N30.26523 (11)0.43926 (12)0.82068 (7)0.0333 (3)
N40.20199 (15)0.37086 (14)0.76506 (7)0.0493 (4)
N50.29902 (14)0.54902 (14)0.71559 (7)0.0480 (4)
O10.48087 (11)0.26108 (12)0.95828 (7)0.0489 (3)
O20.54273 (14)0.19350 (14)1.07513 (8)0.0728 (4)
O30.39307 (11)0.37876 (12)1.13978 (6)0.0483 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0739 (14)0.0835 (15)0.0539 (12)0.0117 (12)0.0255 (11)0.0014 (11)
C20.0384 (8)0.0575 (10)0.0330 (8)−0.0004 (7)0.0014 (7)0.0014 (7)
C30.0376 (8)0.0376 (8)0.0342 (8)0.0000 (6)−0.0007 (6)0.0019 (6)
C40.0355 (7)0.0366 (8)0.0244 (7)−0.0050 (6)−0.0027 (6)0.0015 (6)
C50.0550 (10)0.0399 (9)0.0396 (9)0.0056 (8)0.0063 (7)0.0032 (7)
C60.0690 (12)0.0441 (10)0.0545 (11)0.0053 (9)0.0079 (9)0.0184 (8)
C70.0506 (10)0.0657 (12)0.0391 (9)−0.0011 (9)0.0075 (8)0.0184 (9)
C80.0350 (7)0.0313 (7)0.0251 (7)0.0066 (6)0.0005 (5)0.0022 (6)
C90.0506 (9)0.0391 (8)0.0315 (8)−0.0036 (7)0.0015 (7)0.0032 (6)
C100.0851 (13)0.0421 (9)0.0266 (8)−0.0038 (9)−0.0074 (8)0.0010 (7)
C110.0397 (8)0.0327 (7)0.0288 (7)−0.0079 (6)−0.0026 (6)0.0006 (6)
C120.0433 (8)0.0432 (9)0.0299 (8)−0.0055 (7)−0.0073 (6)0.0053 (6)
C130.0548 (10)0.0458 (9)0.0314 (8)−0.0127 (8)−0.0031 (7)−0.0007 (7)
C140.0484 (9)0.0384 (8)0.0293 (8)−0.0109 (7)−0.0002 (6)−0.0039 (6)
C150.0562 (10)0.0441 (9)0.0446 (10)−0.0039 (8)0.0026 (8)−0.0078 (8)
C160.0748 (14)0.0521 (11)0.0622 (13)−0.0078 (10)0.0193 (11)−0.0165 (10)
C170.1013 (17)0.0632 (13)0.0436 (11)−0.0217 (13)0.0244 (11)−0.0197 (10)
C180.0886 (15)0.0665 (13)0.0284 (9)−0.0230 (12)0.0022 (9)−0.0039 (8)
C190.0460 (9)0.0422 (9)0.0476 (10)−0.0026 (7)−0.0100 (7)0.0091 (8)
C200.0551 (11)0.0507 (11)0.0885 (16)0.0111 (9)0.0140 (11)−0.0061 (11)
C210.0790 (15)0.0770 (15)0.0782 (16)−0.0006 (12)0.0305 (12)−0.0226 (13)
N10.0470 (7)0.0353 (7)0.0236 (6)−0.0040 (6)0.0019 (5)−0.0024 (5)
N20.0454 (7)0.0323 (6)0.0254 (6)0.0009 (5)−0.0027 (5)0.0007 (5)
N30.0436 (7)0.0317 (6)0.0245 (6)0.0020 (5)−0.0015 (5)0.0006 (5)
N40.0785 (10)0.0414 (8)0.0276 (7)−0.0099 (7)−0.0090 (7)0.0008 (6)
N50.0713 (10)0.0438 (8)0.0289 (7)−0.0030 (7)0.0017 (6)0.0047 (6)
O10.0483 (7)0.0495 (7)0.0489 (7)0.0125 (5)0.0013 (5)0.0001 (6)
O20.0816 (10)0.0638 (9)0.0719 (10)0.0232 (8)−0.0223 (8)0.0150 (7)
O30.0609 (7)0.0542 (7)0.0291 (6)−0.0065 (6)−0.0107 (5)0.0067 (5)

Geometric parameters (Å, °)

C1—C21.502 (3)C11—C141.442 (2)
C1—H1A0.9600C12—O31.3895 (18)
C1—H1B0.9600C12—C191.454 (2)
C1—H1C0.9600C13—O31.366 (2)
C2—C71.383 (2)C13—C141.383 (2)
C2—C31.387 (2)C13—C181.383 (2)
C3—C41.382 (2)C14—C151.392 (2)
C3—H30.9300C15—C161.377 (2)
C4—C51.381 (2)C15—H150.9300
C4—N11.4177 (18)C16—C171.391 (3)
C5—C61.381 (2)C16—H160.9300
C5—H50.9300C17—C181.373 (3)
C6—C71.376 (3)C17—H170.9300
C6—H60.9300C18—H180.9300
C7—H70.9300C19—O21.1993 (19)
C8—N21.2735 (18)C19—O11.328 (2)
C8—N11.3481 (19)C20—O11.440 (2)
C8—N31.4287 (17)C20—C211.486 (3)
C9—N51.3105 (19)C20—H20A0.9700
C9—N31.3391 (19)C20—H20B0.9700
C9—H90.9300C21—H21A0.9600
C10—N41.303 (2)C21—H21B0.9600
C10—N51.354 (2)C21—H21C0.9600
C10—H100.9300N1—H10.862 (17)
C11—C121.362 (2)N3—N41.3626 (17)
C11—N21.3962 (18)
C2—C1—H1A109.5C13—C14—C15119.15 (15)
C2—C1—H1B109.5C13—C14—C11105.87 (15)
H1A—C1—H1B109.5C15—C14—C11134.89 (15)
C2—C1—H1C109.5C16—C15—C14118.35 (18)
H1A—C1—H1C109.5C16—C15—H15120.8
H1B—C1—H1C109.5C14—C15—H15120.8
C7—C2—C3117.90 (16)C15—C16—C17121.1 (2)
C7—C2—C1121.85 (16)C15—C16—H16119.4
C3—C2—C1120.23 (16)C17—C16—H16119.4
C4—C3—C2121.35 (15)C18—C17—C16121.55 (18)
C4—C3—H3119.3C18—C17—H17119.2
C2—C3—H3119.3C16—C17—H17119.2
C5—C4—C3119.88 (14)C17—C18—C13116.53 (18)
C5—C4—N1119.40 (14)C17—C18—H18121.7
C3—C4—N1120.64 (13)C13—C18—H18121.7
C4—C5—C6119.21 (16)O2—C19—O1124.70 (18)
C4—C5—H5120.4O2—C19—C12124.88 (17)
C6—C5—H5120.4O1—C19—C12110.42 (13)
C7—C6—C5120.53 (17)O1—C20—C21106.89 (16)
C7—C6—H6119.7O1—C20—H20A110.3
C5—C6—H6119.7C21—C20—H20A110.3
C6—C7—C2121.10 (16)O1—C20—H20B110.3
C6—C7—H7119.5C21—C20—H20B110.3
C2—C7—H7119.5H20A—C20—H20B108.6
N2—C8—N1133.19 (13)C20—C21—H21A109.5
N2—C8—N3115.11 (13)C20—C21—H21B109.5
N1—C8—N3111.70 (12)H21A—C21—H21B109.5
N5—C9—N3110.52 (14)C20—C21—H21C109.5
N5—C9—H9124.7H21A—C21—H21C109.5
N3—C9—H9124.7H21B—C21—H21C109.5
N4—C10—N5115.89 (15)C8—N1—C4125.58 (12)
N4—C10—H10122.1C8—N1—H1117.1 (11)
N5—C10—H10122.1C4—N1—H1116.9 (11)
C12—C11—N2130.93 (14)C8—N2—C11123.48 (12)
C12—C11—C14105.98 (13)C9—N3—N4109.44 (12)
N2—C11—C14122.90 (14)C9—N3—C8129.64 (13)
C11—C12—O3111.34 (14)N4—N3—C8120.89 (12)
C11—C12—C19134.03 (15)C10—N4—N3101.83 (13)
O3—C12—C19114.62 (13)C9—N5—C10102.30 (13)
O3—C13—C14111.09 (14)C19—O1—C20117.17 (14)
O3—C13—C18125.62 (16)C13—O3—C12105.68 (12)
C14—C13—C18123.29 (18)
C7—C2—C3—C4−1.8 (2)O3—C12—C19—O20.2 (2)
C1—C2—C3—C4179.70 (16)C11—C12—C19—O11.1 (3)
C2—C3—C4—C50.3 (2)O3—C12—C19—O1179.71 (13)
C2—C3—C4—N1177.05 (13)N2—C8—N1—C418.8 (3)
C3—C4—C5—C61.4 (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—C844.1 (2)
C5—C6—C7—C2−0.1 (3)N1—C8—N2—C119.3 (3)
C3—C2—C7—C61.7 (3)N3—C8—N2—C11−171.20 (13)
C1—C2—C7—C6−179.82 (18)C12—C11—N2—C862.4 (2)
N2—C11—C12—O3176.20 (14)C14—C11—N2—C8−123.30 (16)
C14—C11—C12—O31.20 (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—C19179.85 (17)N2—C8—N3—C912.4 (2)
O3—C13—C14—C15179.20 (14)N1—C8—N3—C9−168.00 (15)
C18—C13—C14—C150.3 (3)N2—C8—N3—N4−165.31 (14)
O3—C13—C14—C112.24 (18)N1—C8—N3—N414.28 (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—C100.83 (18)
N2—C11—C14—C13−177.55 (14)C8—N3—N4—C10178.97 (14)
C12—C11—C14—C15−178.31 (18)N3—C9—N5—C100.34 (19)
N2—C11—C14—C156.2 (3)N4—C10—N5—C90.2 (2)
C13—C14—C15—C16−0.3 (2)O2—C19—O1—C204.3 (3)
C11—C14—C15—C16175.60 (17)C12—C19—O1—C20−175.22 (14)
C14—C15—C16—C170.5 (3)C21—C20—O1—C19179.39 (16)
C15—C16—C17—C18−0.7 (3)C14—C13—O3—C12−1.52 (17)
C16—C17—C18—C130.7 (3)C18—C13—O3—C12177.38 (16)
O3—C13—C18—C17−179.23 (16)C11—C12—O3—C130.14 (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, °)

D—H···AD—HH···AD···AD—H···A
C10—H10···O2i0.932.433.271 (2)150
N1—H1···N5ii0.862 (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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JH2221).

References

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography