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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2782.
Published online 2010 October 9. doi:  10.1107/S160053681003847X
PMCID: PMC3009276

5-(3-Chloro­phen­yl)-2-phenyl-3,4-dihydro-2H-pyrrole

Abstract

In the title compound, C16H14ClN, the conformation of the five-membered ring approximates to an envelope with a C atom as the flap. The dihedral angle between the aromatic rings is 78.71 (9)°.

Related literature

For chemical background to pyrrolines, see: Tsuge et al. (1987 [triangle]).

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Object name is e-66-o2782-scheme1.jpg

Experimental

Crystal data

  • C16H14ClN
  • M r = 255.73
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2782-efi1.jpg
  • a = 18.2543 (18) Å
  • b = 5.6398 (5) Å
  • c = 13.0095 (13) Å
  • β = 97.129 (2)°
  • V = 1329.0 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.27 mm−1
  • T = 296 K
  • 0.38 × 0.32 × 0.20 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.905, T max = 0.948
  • 6409 measured reflections
  • 2344 independent reflections
  • 1856 reflections with I > 2σ(I)
  • R int = 0.017

Refinement

  • R[F 2 > 2σ(F 2)] = 0.033
  • wR(F 2) = 0.091
  • S = 1.06
  • 2344 reflections
  • 163 parameters
  • H-atom parameters constrained
  • Δρmax = 0.13 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [triangle]); data reduction: SAINT; 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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681003847X/hb5651sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681003847X/hb5651Isup2.hkl

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

supplementary crystallographic information

Experimental

To a 500 ml flask N-(4-(3-chlorophenyl)-4-oxo-1-phenylbutyl)acetamide (6.25 g, 19.79 mmol), 40 mL 6M Hydrochloric acid aqueous solution and 120 ml e thanol were added sequentially. The reaction mixture was heated to reflux and reacted for 20 h. After separation through silica gel column chromatography (fluent: ethyl acetate/petroleum ether=1/20), The title product compound was gained as a pale yellow solid (3.50 g, 69%) and recrystallised from methylene chloride to yield colourless blocks of (I).

Anal. Calcd for C16H14Cl1N1: C, 75.14; H, 5.52; Cl, 13.86; N, 5.48. Found: C, 75.22; H, 5.50; N, 5.45. 1H NMR(CDCl3): 1.94(m,1H, N—CH—CH1),2.83 (m,1H, N—CH—CH1), 3.02(m, 1H, N=C—CH1), 3.15 (m, 1H, N=C—CH1), 5.33 (t, 1H,C=N—CH1),7.28–7.88(m, 9H, Ph—H).

Refinement

Although all H atoms were visible in difference maps, they were finally placed in geometrically calculated positions, with C—H distances in the range 0.93–0.98 Å, and included in the final refinement in the riding model approximation,with Uiso(H) = 1.1Ueq(C, N) and Uiso(H) = 1.1Ueq(C).

Figures

Fig. 1.
The molecular structure of (I), with 30% probability displacement ellipsoids.
Fig. 2.
Crystal packing of (I).

Crystal data

C16H14ClNF(000) = 536
Mr = 255.73Dx = 1.278 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2445 reflections
a = 18.2543 (18) Åθ = 3.2–25.0°
b = 5.6398 (5) ŵ = 0.27 mm1
c = 13.0095 (13) ÅT = 296 K
β = 97.129 (2)°Block, colourless
V = 1329.0 (2) Å30.38 × 0.32 × 0.20 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer2344 independent reflections
Radiation source: fine-focus sealed tube1856 reflections with I > 2σ(I)
graphiteRint = 0.017
phi and ω scansθmax = 25.0°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −21→21
Tmin = 0.905, Tmax = 0.948k = −6→4
6409 measured reflectionsl = −14→15

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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0407P)2 + 0.239P] where P = (Fo2 + 2Fc2)/3
2344 reflections(Δ/σ)max < 0.001
163 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = −0.18 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Cl10.46600 (3)−0.37904 (9)0.67127 (4)0.07239 (19)
N10.26607 (7)0.2985 (3)0.70282 (10)0.0606 (4)
C10.36885 (8)−0.0215 (3)0.63059 (11)0.0477 (4)
H10.3644−0.02420.70100.057*
C20.41540 (8)−0.1765 (3)0.59008 (12)0.0514 (4)
C30.42310 (9)−0.1765 (4)0.48568 (13)0.0625 (5)
H30.4547−0.28340.45910.075*
C40.38333 (9)−0.0163 (4)0.42214 (13)0.0669 (5)
H40.3883−0.01400.35180.080*
C50.33616 (9)0.1414 (3)0.46108 (12)0.0573 (4)
H50.30960.24920.41700.069*
C60.32813 (8)0.1401 (3)0.56578 (11)0.0462 (4)
C70.27682 (8)0.3056 (3)0.60801 (11)0.0480 (4)
C80.23478 (9)0.4944 (3)0.54365 (13)0.0548 (4)
H8A0.26770.61610.52330.066*
H8B0.20700.42740.48200.066*
C90.18419 (12)0.5915 (4)0.61625 (14)0.0760 (6)
H9A0.13370.54080.59570.091*
H9B0.18570.76350.61740.091*
C100.21413 (9)0.4885 (3)0.72331 (13)0.0589 (4)
H100.24200.61310.76360.071*
C110.15575 (8)0.3978 (3)0.78499 (12)0.0505 (4)
C120.13832 (10)0.5176 (3)0.87106 (13)0.0601 (5)
H120.16350.65650.89160.072*
C130.08427 (11)0.4353 (4)0.92721 (16)0.0761 (6)
H130.07350.51840.98520.091*
C140.04680 (11)0.2338 (4)0.89818 (18)0.0795 (6)
H140.01020.17930.93600.095*
C150.06289 (12)0.1112 (4)0.8137 (2)0.0839 (6)
H150.0373−0.02720.79370.101*
C160.11725 (11)0.1926 (4)0.75748 (16)0.0719 (5)
H160.12810.10730.70010.086*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0734 (3)0.0730 (3)0.0733 (3)0.0237 (2)0.0194 (2)0.0061 (2)
N10.0599 (8)0.0775 (10)0.0437 (8)0.0241 (8)0.0038 (6)−0.0048 (7)
C10.0469 (8)0.0571 (10)0.0401 (8)−0.0006 (7)0.0087 (6)−0.0050 (7)
C20.0442 (8)0.0575 (10)0.0536 (9)−0.0003 (7)0.0105 (7)−0.0047 (8)
C30.0532 (9)0.0790 (13)0.0581 (10)0.0053 (9)0.0177 (8)−0.0161 (10)
C40.0605 (10)0.1011 (15)0.0413 (9)0.0014 (10)0.0155 (8)−0.0081 (10)
C50.0534 (9)0.0760 (12)0.0425 (9)0.0009 (9)0.0064 (7)0.0010 (8)
C60.0426 (8)0.0557 (10)0.0402 (8)−0.0028 (7)0.0046 (6)−0.0057 (7)
C70.0467 (8)0.0550 (10)0.0415 (8)0.0014 (7)0.0019 (6)−0.0047 (7)
C80.0580 (9)0.0512 (10)0.0542 (9)−0.0003 (8)0.0031 (8)0.0030 (8)
C90.0848 (13)0.0769 (14)0.0667 (12)0.0310 (11)0.0118 (10)0.0077 (10)
C100.0606 (10)0.0617 (11)0.0543 (10)0.0154 (9)0.0061 (8)−0.0110 (9)
C110.0526 (9)0.0463 (9)0.0503 (9)0.0123 (7)−0.0026 (7)−0.0103 (7)
C120.0645 (10)0.0562 (11)0.0597 (10)0.0026 (9)0.0080 (8)−0.0168 (9)
C130.0760 (13)0.0863 (15)0.0690 (12)0.0065 (11)0.0213 (10)−0.0087 (11)
C140.0666 (12)0.0777 (15)0.0946 (16)0.0033 (11)0.0111 (11)0.0177 (13)
C150.0753 (13)0.0512 (12)0.1202 (19)−0.0043 (10)−0.0082 (13)−0.0044 (12)
C160.0749 (12)0.0584 (12)0.0803 (13)0.0084 (10)0.0011 (10)−0.0247 (10)

Geometric parameters (Å, °)

Cl1—C21.7410 (17)C8—H8B0.9700
N1—C71.2733 (19)C9—C101.545 (2)
N1—C101.477 (2)C9—H9A0.9700
C1—C21.369 (2)C9—H9B0.9700
C1—C61.392 (2)C10—C111.501 (2)
C1—H10.9300C10—H100.9800
C2—C31.383 (2)C11—C161.378 (2)
C3—C41.370 (3)C11—C121.378 (2)
C3—H30.9300C12—C131.379 (3)
C4—C51.377 (2)C12—H120.9300
C4—H40.9300C13—C141.356 (3)
C5—C61.388 (2)C13—H130.9300
C5—H50.9300C14—C151.361 (3)
C6—C71.476 (2)C14—H140.9300
C7—C81.505 (2)C15—C161.382 (3)
C8—C91.504 (2)C15—H150.9300
C8—H8A0.9700C16—H160.9300
C7—N1—C10109.37 (14)C8—C9—H9A110.8
C2—C1—C6119.66 (14)C10—C9—H9A110.8
C2—C1—H1120.2C8—C9—H9B110.8
C6—C1—H1120.2C10—C9—H9B110.8
C1—C2—C3121.45 (16)H9A—C9—H9B108.9
C1—C2—Cl1119.55 (12)N1—C10—C11111.31 (15)
C3—C2—Cl1119.01 (13)N1—C10—C9105.86 (13)
C4—C3—C2118.80 (16)C11—C10—C9114.51 (14)
C4—C3—H3120.6N1—C10—H10108.3
C2—C3—H3120.6C11—C10—H10108.3
C3—C4—C5120.82 (15)C9—C10—H10108.3
C3—C4—H4119.6C16—C11—C12117.45 (17)
C5—C4—H4119.6C16—C11—C10121.35 (15)
C4—C5—C6120.29 (16)C12—C11—C10121.19 (16)
C4—C5—H5119.9C11—C12—C13121.18 (18)
C6—C5—H5119.9C11—C12—H12119.4
C5—C6—C1118.98 (15)C13—C12—H12119.4
C5—C6—C7120.74 (15)C14—C13—C12120.27 (19)
C1—C6—C7120.28 (13)C14—C13—H13119.9
N1—C7—C6121.47 (14)C12—C13—H13119.9
N1—C7—C8115.58 (14)C13—C14—C15119.9 (2)
C6—C7—C8122.94 (13)C13—C14—H14120.0
C9—C8—C7102.64 (14)C15—C14—H14120.0
C9—C8—H8A111.2C14—C15—C16120.0 (2)
C7—C8—H8A111.2C14—C15—H15120.0
C9—C8—H8B111.2C16—C15—H15120.0
C7—C8—H8B111.2C11—C16—C15121.21 (18)
H8A—C8—H8B109.2C11—C16—H16119.4
C8—C9—C10104.67 (14)C15—C16—H16119.4
C6—C1—C2—C30.0 (2)C7—C8—C9—C1012.4 (2)
C6—C1—C2—Cl1−179.78 (12)C7—N1—C10—C11134.21 (15)
C1—C2—C3—C40.4 (3)C7—N1—C10—C99.2 (2)
Cl1—C2—C3—C4−179.80 (14)C8—C9—C10—N1−13.5 (2)
C2—C3—C4—C5−0.4 (3)C8—C9—C10—C11−136.50 (16)
C3—C4—C5—C6−0.1 (3)N1—C10—C11—C16−48.5 (2)
C4—C5—C6—C10.5 (2)C9—C10—C11—C1671.5 (2)
C4—C5—C6—C7−178.99 (16)N1—C10—C11—C12131.90 (16)
C2—C1—C6—C5−0.5 (2)C9—C10—C11—C12−108.09 (19)
C2—C1—C6—C7179.01 (14)C16—C11—C12—C13−0.2 (3)
C10—N1—C7—C6178.25 (14)C10—C11—C12—C13179.46 (17)
C10—N1—C7—C8−1.0 (2)C11—C12—C13—C14−0.3 (3)
C5—C6—C7—N1176.41 (16)C12—C13—C14—C150.4 (3)
C1—C6—C7—N1−3.0 (2)C13—C14—C15—C16−0.1 (3)
C5—C6—C7—C8−4.4 (2)C12—C11—C16—C150.5 (3)
C1—C6—C7—C8176.10 (14)C10—C11—C16—C15−179.16 (17)
N1—C7—C8—C9−7.8 (2)C14—C15—C16—C11−0.3 (3)
C6—C7—C8—C9173.00 (15)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5651).

References

  • Bruker (2001). SMART, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Tsuge, O., Ueno, K., Kanemasa, S. & Yorozu, K. (1987). Bull. Chem. Soc. Jpn, 60, 3347–3358.

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