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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

1-Benzyl-N-methyl-1H-pyrrole-2-carboxamide

aDepartment of Chemistry, Jinan University, Guangzhou, Guangdong 510632, People's Republic of China
*Correspondence e-mail: xczeng@126.com

(Received 2 July 2010; accepted 13 July 2010; online 17 July 2010)

The asymmetric unit of the title compound, C13H14N2O, contains two independent mol­ecules, which differ in the twist of the phenyl ring: the Npyrrole—C(H2)—C—C torsion angles are −73.0 (3) and 17.1 (3)°. In the crystal structure, mol­ecules are linked through N—H⋯O hydrogen bonds into chains extending along the a axis.

Related literature

For the bioactivity of pyrrole derivatives, see: Fabio et al. (2007[Fabio, R. D., Micheli, F., Alvaro, G., Cavanni, P., Donati, D., Gagliardi, T., Fontana, G., Giovannini, R., Maffeis, M., Mingardi, A., Tranquillini, M. E. & Vitulli, G. (2007). Bioorg. Med. Chem. Lett. 17, 2254-2259.]); Banwell et al. (2006[Banwell, M. G., Hamel, E., Hockless, D. C. R., Verdier-Pinard, P., Willis, A. C. & Wong, D. J. (2006). Bioorg. Med. Chem. 14, 4627-4638.]). For related structures, see: Zeng et al. (2007[Zeng, X.-C., Zeng, J., Li, X. & Ling, X. (2007). Acta Cryst. E63, o3424.]); Li et al. (2009[Li, D. D., Tang, G. H., Zeng, X. C., Huang, G. & Xu, X. Y. (2009). Acta Cryst. E65, o1865.]).

[Scheme 1]

Experimental

Crystal data
  • C13H14N2O

  • Mr = 214.26

  • Monoclinic, P 21 /c

  • a = 9.8285 (18) Å

  • b = 23.588 (4) Å

  • c = 9.9230 (17) Å

  • β = 90.107 (3)°

  • V = 2300.5 (7) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 110 K

  • 0.45 × 0.43 × 0.41 mm

Data collection
  • Bruker SMART 1K CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.965, Tmax = 0.968

  • 10728 measured reflections

  • 4879 independent reflections

  • 4388 reflections with I > 2σ(I)

  • Rint = 0.033

Refinement
  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 0.157

  • S = 1.03

  • 4879 reflections

  • 300 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.24 e Å−3

  • Δρmin = −0.32 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N4—H4⋯O1i 0.87 (3) 2.04 (3) 2.869 (2) 161 (3)
N2—H2A⋯O3ii 0.86 (4) 2.10 (4) 2.902 (2) 154 (3)
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z-1.

Data collection: SMART (Bruker, 1999[Bruker (1999). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 1999[Bruker (1999). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Many pyrrole derivatives show important bioactivities, such as metabotropic receptor antagonists (Fabio et al., 2007) and antitumor activity (Banwell et al., 2006). This is the reason they have attracted our interest. This study is related to our previous structural investigations of methyl 2-(4,5-dibromo-1H-pyrrole-2-carboxamido)propionate (Zeng et al., 2007) and 3-(1-ethyl-1H-pyrrole-2-carboxamido) propionic acid monohydrate (Li et al., 2009).

In the molecule of the title compound(Fig.1), bond lengths and angles are unexceptional. In the crystal structure, molecules are linked through N—H···O hydrogen bonds, forming chains extending to the a axis (Fig. 2).

Related literature top

For the bioactivity of pyrrole derivatives, see: Fabio et al. (2007); Banwell et al. (2006). For related structures, see: Zeng et al. (2007); Li et al. (2009).

Experimental top

A suspension of potassium carbonate (4.21 g, 30 mmol), chloromethylbenzene (1.7 ml, 15 mmol), Pyrrole-2-carboxylic acid methylamide (1.24 g, 10 mmol) and Tetrabutylammoniumbromide (0.1 g) in acetonitrile (25 ml) magnetically stirred at 353 K for 18 h. After filtration, the filtrate was evaporated in vacuo, and the crude compound (I) was obtained. The impure product was dissolved in EtOH, colourless crystals suitable for X-ray analysis, m.p. 365 K, 92.1%, were obtained over a period of one week by slow evaporation at room temperature of the solution.

Refinement top

The H atoms bonded to N2 and N4 were found on a difference Fourier map and refined isotropically with N—H = 0.86 (4)Å and 0.87 (3)Å respectively. Remaining H atoms were positioned geometrically [C—H = 0.99Å for CH2, 0.98Å for CH3 and 0.95Å for CH(aromatic)] and refined using a riding model, with Uiso = 1.2Ueq (1.5Ueq for the methyl group) of the parent atom.

Structure description top

Many pyrrole derivatives show important bioactivities, such as metabotropic receptor antagonists (Fabio et al., 2007) and antitumor activity (Banwell et al., 2006). This is the reason they have attracted our interest. This study is related to our previous structural investigations of methyl 2-(4,5-dibromo-1H-pyrrole-2-carboxamido)propionate (Zeng et al., 2007) and 3-(1-ethyl-1H-pyrrole-2-carboxamido) propionic acid monohydrate (Li et al., 2009).

In the molecule of the title compound(Fig.1), bond lengths and angles are unexceptional. In the crystal structure, molecules are linked through N—H···O hydrogen bonds, forming chains extending to the a axis (Fig. 2).

For the bioactivity of pyrrole derivatives, see: Fabio et al. (2007); Banwell et al. (2006). For related structures, see: Zeng et al. (2007); Li et al. (2009).

Computing details top

Data collection: SMART (Bruker,1999); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Two independent molecules of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Crystal packing of (I) showing the chains formed by hydrogen bonds (dashed lines).
1-Benzyl-N-methyl-1H-pyrrole-2-carboxamide top
Crystal data top
C13H14N2ODx = 1.237 Mg m3
Mr = 214.26Melting point: 365 K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.8285 (18) ÅCell parameters from 7113 reflections
b = 23.588 (4) Åθ = 2.2–27.0°
c = 9.9230 (17) ŵ = 0.08 mm1
β = 90.107 (3)°T = 110 K
V = 2300.5 (7) Å3Prism, colourless
Z = 80.45 × 0.43 × 0.41 mm
F(000) = 912
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer
4879 independent reflections
Radiation source: fine-focus sealed tube4388 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
φ and ω scansθmax = 27.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1212
Tmin = 0.965, Tmax = 0.968k = 3018
10728 measured reflectionsl = 812
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.1044P)2 + 0.2726P]
where P = (Fo2 + 2Fc2)/3
4879 reflections(Δ/σ)max = 0.001
300 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.32 e Å3
Crystal data top
C13H14N2OV = 2300.5 (7) Å3
Mr = 214.26Z = 8
Monoclinic, P21/cMo Kα radiation
a = 9.8285 (18) ŵ = 0.08 mm1
b = 23.588 (4) ÅT = 110 K
c = 9.9230 (17) Å0.45 × 0.43 × 0.41 mm
β = 90.107 (3)°
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer
4879 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4388 reflections with I > 2σ(I)
Tmin = 0.965, Tmax = 0.968Rint = 0.033
10728 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0550 restraints
wR(F2) = 0.157H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.24 e Å3
4879 reflectionsΔρmin = 0.32 e Å3
300 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
xyzUiso*/Ueq
O30.26038 (14)0.34460 (7)1.12858 (15)0.0345 (4)
N40.46989 (19)0.36072 (8)1.21438 (18)0.0298 (4)
O10.75946 (15)0.35421 (7)0.24801 (16)0.0351 (4)
C180.38669 (19)0.34269 (8)1.11684 (19)0.0248 (4)
N30.38660 (18)0.31280 (7)0.87447 (16)0.0278 (4)
C50.8847 (2)0.34954 (8)0.2623 (2)0.0261 (4)
C40.94580 (19)0.32331 (7)0.3830 (2)0.0251 (4)
N10.87834 (18)0.31770 (7)0.50486 (17)0.0284 (4)
C31.0677 (2)0.29404 (8)0.3945 (2)0.0299 (4)
H31.13470.29030.32620.036*
C210.2777 (2)0.39956 (8)0.7816 (2)0.0276 (4)
C170.4525 (2)0.31943 (8)0.9961 (2)0.0254 (4)
N20.97245 (19)0.36613 (8)0.16790 (19)0.0325 (4)
C70.7549 (2)0.34689 (9)0.5492 (2)0.0318 (4)
H7A0.70100.32070.60580.038*
H7B0.69940.35640.46900.038*
C160.5796 (2)0.29413 (8)0.9852 (2)0.0305 (4)
H160.64690.29201.05390.037*
C250.3206 (3)0.49865 (10)0.8254 (3)0.0427 (5)
H250.33900.52840.88730.051*
C150.5903 (3)0.27231 (9)0.8536 (2)0.0378 (5)
H150.66590.25250.81700.045*
C80.7817 (2)0.40061 (8)0.6283 (2)0.0289 (4)
C200.2580 (2)0.33927 (9)0.8305 (2)0.0305 (4)
H20A0.19310.33930.90670.037*
H20B0.21780.31630.75690.037*
C190.4191 (2)0.37479 (11)1.3473 (2)0.0387 (5)
H19A0.32380.38671.34040.058*
H19B0.47350.40571.38550.058*
H19C0.42560.34141.40580.058*
C110.8202 (3)0.50016 (11)0.7752 (3)0.0442 (5)
H110.83340.53410.82510.053*
C10.9583 (3)0.28673 (8)0.5899 (2)0.0355 (5)
H10.93660.27750.68050.043*
C140.4714 (3)0.28490 (8)0.7884 (2)0.0345 (5)
H140.45110.27570.69740.041*
C220.2682 (2)0.41183 (9)0.6454 (2)0.0338 (5)
H220.25010.38220.58300.041*
C260.3042 (2)0.44347 (9)0.8715 (2)0.0371 (5)
H260.31110.43570.96520.044*
C60.9276 (3)0.38588 (13)0.0361 (3)0.0497 (6)
H6A0.89890.35340.01860.075*
H6B1.00270.40550.00900.075*
H6C0.85100.41200.04700.075*
C90.6769 (2)0.42377 (10)0.7042 (2)0.0379 (5)
H90.59090.40540.70660.045*
C21.0749 (2)0.27108 (8)0.5242 (2)0.0347 (5)
H21.14690.24880.56010.042*
C130.9061 (2)0.42821 (10)0.6273 (2)0.0378 (5)
H130.97900.41320.57560.045*
C230.2847 (3)0.46671 (10)0.5993 (2)0.0423 (5)
H230.27850.47460.50560.051*
C100.6962 (3)0.47337 (11)0.7765 (3)0.0447 (6)
H100.62330.48890.82720.054*
C120.9253 (3)0.47759 (11)0.7011 (3)0.0469 (6)
H121.01140.49590.70040.056*
C240.3101 (3)0.51017 (10)0.6894 (3)0.0426 (5)
H240.32030.54790.65770.051*
H2A1.058 (4)0.3631 (12)0.183 (3)0.051 (8)*
H40.557 (3)0.3597 (11)1.204 (3)0.044 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0196 (6)0.0549 (9)0.0290 (7)0.0027 (6)0.0040 (6)0.0056 (7)
N40.0200 (8)0.0428 (9)0.0267 (8)0.0019 (7)0.0021 (7)0.0066 (7)
O10.0200 (7)0.0510 (9)0.0342 (7)0.0021 (6)0.0005 (6)0.0048 (7)
C180.0228 (8)0.0286 (8)0.0231 (8)0.0006 (7)0.0033 (8)0.0014 (7)
N30.0334 (9)0.0271 (7)0.0230 (7)0.0028 (6)0.0040 (7)0.0011 (6)
C50.0221 (9)0.0259 (8)0.0301 (9)0.0001 (7)0.0010 (8)0.0020 (8)
C40.0235 (9)0.0258 (8)0.0261 (9)0.0012 (7)0.0017 (8)0.0031 (7)
N10.0292 (8)0.0297 (8)0.0263 (8)0.0001 (7)0.0027 (7)0.0007 (7)
C30.0288 (9)0.0297 (9)0.0311 (10)0.0050 (7)0.0019 (9)0.0038 (8)
C210.0216 (8)0.0337 (10)0.0276 (9)0.0015 (7)0.0028 (8)0.0002 (8)
C170.0246 (9)0.0269 (8)0.0249 (9)0.0021 (7)0.0063 (8)0.0023 (7)
N20.0220 (8)0.0439 (10)0.0315 (9)0.0032 (7)0.0047 (7)0.0066 (8)
C70.0251 (10)0.0390 (11)0.0313 (9)0.0027 (8)0.0067 (9)0.0027 (8)
C160.0296 (10)0.0313 (9)0.0307 (10)0.0058 (8)0.0091 (9)0.0047 (8)
C250.0439 (12)0.0329 (10)0.0512 (13)0.0004 (9)0.0023 (12)0.0046 (10)
C150.0473 (13)0.0321 (9)0.0339 (11)0.0097 (9)0.0157 (10)0.0006 (9)
C80.0275 (9)0.0339 (9)0.0251 (8)0.0022 (8)0.0007 (8)0.0024 (8)
C200.0309 (10)0.0345 (10)0.0260 (8)0.0067 (8)0.0001 (8)0.0001 (8)
C190.0307 (11)0.0574 (13)0.0280 (10)0.0063 (10)0.0003 (9)0.0112 (9)
C110.0467 (13)0.0429 (12)0.0431 (12)0.0042 (10)0.0025 (11)0.0125 (10)
C10.0455 (13)0.0323 (10)0.0287 (10)0.0005 (9)0.0043 (10)0.0017 (8)
C140.0493 (13)0.0276 (10)0.0265 (9)0.0036 (9)0.0080 (10)0.0031 (8)
C220.0370 (11)0.0386 (11)0.0260 (9)0.0064 (9)0.0037 (8)0.0001 (9)
C260.0419 (12)0.0367 (10)0.0325 (10)0.0014 (9)0.0046 (10)0.0030 (9)
C60.0376 (12)0.0753 (17)0.0362 (11)0.0101 (12)0.0077 (11)0.0211 (12)
C90.0288 (10)0.0461 (12)0.0387 (11)0.0016 (9)0.0055 (10)0.0029 (10)
C20.0395 (11)0.0315 (10)0.0329 (10)0.0082 (9)0.0063 (9)0.0026 (8)
C130.0272 (10)0.0441 (11)0.0421 (11)0.0009 (9)0.0057 (10)0.0089 (10)
C230.0497 (14)0.0452 (12)0.0320 (10)0.0104 (10)0.0063 (11)0.0113 (10)
C100.0369 (12)0.0518 (14)0.0454 (13)0.0097 (10)0.0050 (11)0.0117 (11)
C120.0347 (12)0.0497 (13)0.0563 (15)0.0080 (10)0.0001 (12)0.0131 (12)
C240.0402 (12)0.0340 (11)0.0536 (13)0.0057 (9)0.0065 (11)0.0103 (10)
Geometric parameters (Å, º) top
O3—C181.248 (2)C15—C141.367 (4)
N4—C181.335 (3)C15—H150.9500
N4—C191.450 (3)C8—C131.386 (3)
N4—H40.87 (3)C8—C91.390 (3)
O1—C51.243 (2)C20—H20A0.9900
C18—C171.469 (3)C20—H20B0.9900
N3—C141.364 (3)C19—H19A0.9800
N3—C171.378 (3)C19—H19B0.9800
N3—C201.475 (3)C19—H19C0.9800
C5—N21.334 (3)C11—C101.373 (4)
C5—C41.475 (3)C11—C121.376 (4)
C4—N11.386 (3)C11—H110.9500
C4—C31.388 (3)C1—C21.369 (3)
N1—C11.364 (3)C1—H10.9500
N1—C71.463 (3)C14—H140.9500
C3—C21.398 (3)C22—C231.383 (3)
C3—H30.9500C22—H220.9500
C21—C221.385 (3)C26—H260.9500
C21—C261.391 (3)C6—H6A0.9800
C21—C201.515 (3)C6—H6B0.9800
C17—C161.389 (3)C6—H6C0.9800
N2—C61.456 (3)C9—C101.385 (3)
N2—H2A0.86 (4)C9—H90.9500
C7—C81.513 (3)C2—H20.9500
C7—H7A0.9900C13—C121.388 (3)
C7—H7B0.9900C13—H130.9500
C16—C151.408 (3)C23—C241.383 (4)
C16—H160.9500C23—H230.9500
C25—C241.381 (4)C10—H100.9500
C25—C261.389 (3)C12—H120.9500
C25—H250.9500C24—H240.9500
C18—N4—C19121.39 (18)N3—C20—H20B109.1
C18—N4—H4120.7 (19)C21—C20—H20B109.1
C19—N4—H4117.3 (19)H20A—C20—H20B107.8
O3—C18—N4121.92 (18)N4—C19—H19A109.5
O3—C18—C17121.96 (18)N4—C19—H19B109.5
N4—C18—C17116.10 (17)H19A—C19—H19B109.5
C14—N3—C17108.44 (18)N4—C19—H19C109.5
C14—N3—C20122.93 (18)H19A—C19—H19C109.5
C17—N3—C20127.76 (16)H19B—C19—H19C109.5
O1—C5—N2122.4 (2)C10—C11—C12119.6 (2)
O1—C5—C4122.11 (19)C10—C11—H11120.2
N2—C5—C4115.51 (18)C12—C11—H11120.2
N1—C4—C3107.17 (18)N1—C1—C2109.37 (19)
N1—C4—C5123.61 (17)N1—C1—H1125.3
C3—C4—C5128.74 (19)C2—C1—H1125.3
C1—N1—C4108.33 (18)N3—C14—C15109.37 (19)
C1—N1—C7122.91 (18)N3—C14—H14125.3
C4—N1—C7127.97 (17)C15—C14—H14125.3
C4—C3—C2108.07 (19)C23—C22—C21120.7 (2)
C4—C3—H3126.0C23—C22—H22119.6
C2—C3—H3126.0C21—C22—H22119.6
C22—C21—C26118.8 (2)C25—C26—C21120.5 (2)
C22—C21—C20120.01 (18)C25—C26—H26119.7
C26—C21—C20121.14 (18)C21—C26—H26119.7
N3—C17—C16107.72 (18)N2—C6—H6A109.5
N3—C17—C18123.36 (17)N2—C6—H6B109.5
C16—C17—C18128.44 (19)H6A—C6—H6B109.5
C5—N2—C6122.00 (19)N2—C6—H6C109.5
C5—N2—H2A119 (2)H6A—C6—H6C109.5
C6—N2—H2A118 (2)H6B—C6—H6C109.5
N1—C7—C8113.97 (17)C10—C9—C8120.8 (2)
N1—C7—H7A108.8C10—C9—H9119.6
C8—C7—H7A108.8C8—C9—H9119.6
N1—C7—H7B108.8C1—C2—C3107.04 (19)
C8—C7—H7B108.8C1—C2—H2126.5
H7A—C7—H7B107.7C3—C2—H2126.5
C17—C16—C15107.3 (2)C8—C13—C12120.6 (2)
C17—C16—H16126.3C8—C13—H13119.7
C15—C16—H16126.3C12—C13—H13119.7
C24—C25—C26119.9 (2)C24—C23—C22120.1 (2)
C24—C25—H25120.1C24—C23—H23120.0
C26—C25—H25120.1C22—C23—H23120.0
C14—C15—C16107.11 (19)C11—C10—C9120.3 (2)
C14—C15—H15126.4C11—C10—H10119.8
C16—C15—H15126.4C9—C10—H10119.8
C13—C8—C9118.3 (2)C11—C12—C13120.4 (2)
C13—C8—C7122.84 (19)C11—C12—H12119.8
C9—C8—C7118.81 (19)C13—C12—H12119.8
N3—C20—C21112.46 (16)C25—C24—C23119.9 (2)
N3—C20—H20A109.1C25—C24—H24120.0
C21—C20—H20A109.1C23—C24—H24120.0
C19—N4—C18—O310.3 (3)N1—C7—C8—C9163.65 (18)
C19—N4—C18—C17168.55 (18)C14—N3—C20—C2187.5 (2)
O1—C5—C4—N120.5 (3)C17—N3—C20—C2180.6 (2)
N2—C5—C4—N1161.67 (17)C22—C21—C20—N3107.6 (2)
O1—C5—C4—C3150.5 (2)C26—C21—C20—N373.0 (3)
N2—C5—C4—C327.3 (3)C4—N1—C1—C21.4 (2)
C3—C4—N1—C11.2 (2)C7—N1—C1—C2171.95 (18)
C5—C4—N1—C1173.90 (17)C17—N3—C14—C151.3 (2)
C3—C4—N1—C7171.15 (18)C20—N3—C14—C15171.34 (17)
C5—C4—N1—C716.2 (3)C16—C15—C14—N30.9 (2)
N1—C4—C3—C20.6 (2)C26—C21—C22—C230.0 (3)
C5—C4—C3—C2172.77 (19)C20—C21—C22—C23179.4 (2)
C14—N3—C17—C161.1 (2)C24—C25—C26—C210.2 (4)
C20—N3—C17—C16170.53 (17)C22—C21—C26—C250.1 (3)
C14—N3—C17—C18173.73 (17)C20—C21—C26—C25179.3 (2)
C20—N3—C17—C1816.8 (3)C13—C8—C9—C100.3 (3)
O3—C18—C17—N318.7 (3)C7—C8—C9—C10179.0 (2)
N4—C18—C17—N3162.52 (17)N1—C1—C2—C31.0 (2)
O3—C18—C17—C16152.4 (2)C4—C3—C2—C10.2 (2)
N4—C18—C17—C1626.4 (3)C9—C8—C13—C120.4 (4)
O1—C5—N2—C66.0 (3)C7—C8—C13—C12179.6 (2)
C4—C5—N2—C6171.8 (2)C21—C22—C23—C240.4 (4)
C1—N1—C7—C875.4 (2)C12—C11—C10—C90.3 (4)
C4—N1—C7—C893.1 (2)C8—C9—C10—C110.6 (4)
N3—C17—C16—C150.5 (2)C10—C11—C12—C130.4 (4)
C18—C17—C16—C15172.66 (19)C8—C13—C12—C110.7 (4)
C17—C16—C15—C140.3 (2)C26—C25—C24—C230.7 (4)
N1—C7—C8—C1317.1 (3)C22—C23—C24—C250.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···O1i0.87 (3)2.04 (3)2.869 (2)161 (3)
N2—H2A···O3ii0.86 (4)2.10 (4)2.902 (2)154 (3)
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z1.

Experimental details

Crystal data
Chemical formulaC13H14N2O
Mr214.26
Crystal system, space groupMonoclinic, P21/c
Temperature (K)110
a, b, c (Å)9.8285 (18), 23.588 (4), 9.9230 (17)
β (°) 90.107 (3)
V3)2300.5 (7)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.45 × 0.43 × 0.41
Data collection
DiffractometerBruker SMART 1K CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.965, 0.968
No. of measured, independent and
observed [I > 2σ(I)] reflections
10728, 4879, 4388
Rint0.033
(sin θ/λ)max1)0.640
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.157, 1.03
No. of reflections4879
No. of parameters300
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.24, 0.32

Computer programs: SMART (Bruker,1999), SAINT-Plus (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···O1i0.87 (3)2.04 (3)2.869 (2)161 (3)
N2—H2A···O3ii0.86 (4)2.10 (4)2.902 (2)154 (3)
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z1.
 

Acknowledgements

We thank the Natural Science Foundation of Guangdong Province, China (grant No. 06300581) for generous support of this study.

References

First citationBanwell, M. G., Hamel, E., Hockless, D. C. R., Verdier-Pinard, P., Willis, A. C. & Wong, D. J. (2006). Bioorg. Med. Chem. 14, 4627–4638.  Web of Science CrossRef PubMed CAS Google Scholar
First citationBruker (1999). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFabio, R. D., Micheli, F., Alvaro, G., Cavanni, P., Donati, D., Gagliardi, T., Fontana, G., Giovannini, R., Maffeis, M., Mingardi, A., Tranquillini, M. E. & Vitulli, G. (2007). Bioorg. Med. Chem. Lett. 17, 2254–2259.  Web of Science CrossRef PubMed Google Scholar
First citationLi, D. D., Tang, G. H., Zeng, X. C., Huang, G. & Xu, X. Y. (2009). Acta Cryst. E65, o1865.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationZeng, X.-C., Zeng, J., Li, X. & Ling, X. (2007). Acta Cryst. E63, o3424.  Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds