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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): o2051.
Published online 2010 July 17. doi:  10.1107/S160053681002787X
PMCID: PMC3007309

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

Abstract

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 [triangle]); Banwell et al. (2006 [triangle]). For related structures, see: Zeng et al. (2007 [triangle]); Li et al. (2009 [triangle]).

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Object name is e-66-o2051-scheme1.jpg

Experimental

Crystal data

  • C13H14N2O
  • M r = 214.26
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2051-efi1.jpg
  • 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 [triangle]) T min = 0.965, T max = 0.968
  • 10728 measured reflections
  • 4879 independent reflections
  • 4388 reflections with I > 2σ(I)
  • R int = 0.033

Refinement

  • R[F 2 > 2σ(F 2)] = 0.055
  • wR(F 2) = 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

Data collection: SMART (Bruker, 1999 [triangle]); cell refinement: SAINT-Plus (Bruker, 1999 [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: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681002787X/cv2741sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002787X/cv2741Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

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).

Experimental

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

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.

Figures

Fig. 1.
Two independent molecules of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
Crystal packing of (I) showing the chains formed by hydrogen bonds (dashed lines).

Crystal data

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

Bruker SMART 1K CCD area-detector diffractometer4879 independent reflections
Radiation source: fine-focus sealed tube4388 reflections with I > 2σ(I)
graphiteRint = 0.033
[var phi] and ω scansθmax = 27.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −12→12
Tmin = 0.965, Tmax = 0.968k = −30→18
10728 measured reflectionsl = −8→12

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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157H atoms treated by a mixture of independent and constrained refinement
S = 1.02w = 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

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
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)
H6A0.89890.3534−0.01860.075*
H6B1.00270.4055−0.00900.075*
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)

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, °)

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—C9−163.65 (18)
C19—N4—C18—C17−168.55 (18)C14—N3—C20—C21−87.5 (2)
O1—C5—C4—N1−20.5 (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—N3−73.0 (3)
N2—C5—C4—C3−27.3 (3)C4—N1—C1—C2−1.4 (2)
C3—C4—N1—C11.2 (2)C7—N1—C1—C2−171.95 (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—C7−16.2 (3)C16—C15—C14—N3−0.9 (2)
N1—C4—C3—C2−0.6 (2)C26—C21—C22—C230.0 (3)
C5—C4—C3—C2−172.77 (19)C20—C21—C22—C23179.4 (2)
C14—N3—C17—C16−1.1 (2)C24—C25—C26—C210.2 (4)
C20—N3—C17—C16−170.53 (17)C22—C21—C26—C250.1 (3)
C14—N3—C17—C18−173.73 (17)C20—C21—C26—C25−179.3 (2)
C20—N3—C17—C1816.8 (3)C13—C8—C9—C100.3 (3)
O3—C18—C17—N318.7 (3)C7—C8—C9—C10−179.0 (2)
N4—C18—C17—N3−162.52 (17)N1—C1—C2—C31.0 (2)
O3—C18—C17—C16−152.4 (2)C4—C3—C2—C1−0.2 (2)
N4—C18—C17—C1626.4 (3)C9—C8—C13—C120.4 (4)
O1—C5—N2—C6−6.0 (3)C7—C8—C13—C12179.6 (2)
C4—C5—N2—C6171.8 (2)C21—C22—C23—C24−0.4 (4)
C1—N1—C7—C875.4 (2)C12—C11—C10—C90.3 (4)
C4—N1—C7—C8−93.1 (2)C8—C9—C10—C11−0.6 (4)
N3—C17—C16—C150.5 (2)C10—C11—C12—C130.4 (4)
C18—C17—C16—C15172.66 (19)C8—C13—C12—C11−0.7 (4)
C17—C16—C15—C140.3 (2)C26—C25—C24—C23−0.7 (4)
N1—C7—C8—C1317.1 (3)C22—C23—C24—C250.8 (4)

Hydrogen-bond geometry (Å, °)

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, z−1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2741).

References

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