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Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): o2179.
Published online 2008 October 25. doi:  10.1107/S1600536808034077
PMCID: PMC2959514

1-Benzoyl-N-phenyl­cyclo­propane­carboxamide

Abstract

The title compound, C17H15NO2, was synthesized by reaction of 1,2-dibromo­ethane with 1-benzoyl-N-phenyl­cyclo­propane­carboxamide and K2CO3 in dimethyl­formamide. The mol­ecule exhibits a V-shaped conformation in the crystal with a dihedral angle of 88.7 (3)° between the two benzene rings. Pairs of N—H(...)O hydrogen bonds link the mol­ecules into dimers about centres of inversion.

Related literature

For further synthesis details, see: Zhang et al. (2007 [triangle]).

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Object name is e-64-o2179-scheme1.jpg

Experimental

Crystal data

  • C17H15NO2
  • M r = 265.30
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2179-efi1.jpg
  • a = 7.424 (1) Å
  • b = 9.473 (1) Å
  • c = 10.831 (2) Å
  • α = 94.276 (2)°
  • β = 99.313 (2)°
  • γ = 105.773 (2)°
  • V = 717.72 (17) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 293 (2) K
  • 0.32 × 0.24 × 0.21 mm

Data collection

  • Bruker APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.981, T max = 0.986
  • 4053 measured reflections
  • 2748 independent reflections
  • 2213 reflections with I > 2σ(I)
  • R int = 0.012

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.119
  • S = 1.04
  • 2748 reflections
  • 185 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.15 e Å−3
  • Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [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.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808034077/bi2312sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034077/bi2312Isup2.hkl

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

Acknowledgments

We thank the Analysis and Testing Foundation of Northeast Normal University for support.

supplementary crystallographic information

Comment

Derivatives of 1-benzoyl-N-phenylcyclopropanecarboxamide have been long known for their diverse pharmacological and biological properties. The method for the synthesis of similar compounds has been reported previously (Zhang et al., 2007). In the crystal, the title compound exhibits a "V-shaped" conformation with interplanar angle of 91.3 (3)° between the two benzene rings (C1–C6 and C12–C17). The C8–C10 cyclopropane ring makes dihedral angles of 120.8 (3)° and 125.9 (2)° with the C1–C6 and C12–C17 benzene rings, respectively. The value of the dihedral angle between the planes defined by C7—O1—C8 and the C1–C6 ring is 18.8 (3)°.

Experimental

1,2-Dibromoethane (0.95 ml, 11 mmol) was added to a solution of 1-benzoyl-N-phenylcyclopropanecarboxamide (2393 mg, 10 mmol) and K2CO3 (2950 mg, 23 mmol) in DMF (25 ml) and the mixture was stirred for 10 h (monitored by TLC) before being slowly poured into ice-water (200 ml). The precipitated white solid was filtered and purified by flash silica gel column chromatography (eluent: ether/ethyl acetate (1/3)) to give the title compound as colourless crystals.

Refinement

H atoms bound to C atoms were placed geometrically and refined using a riding model with C—H = 0.93 Å for aromatic H or 0.97 Å for CH2 groups, and with Uiso = 1.2Ueq(C). The H atom of the NH group was located in a difference Fourier map and refined with the N—H distance restrained to be 0.88 (1) Å and with Uiso(H) = 1.5Ueq(N).

Figures

Fig. 1.
Molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level for non-H atoms.

Crystal data

C17H15NO2Z = 2
Mr = 265.30F(000) = 280
Triclinic, P1Dx = 1.228 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 7.424 (1) ÅCell parameters from 2748 reflections
b = 9.4730 (13) Åθ = 1.9–26.0°
c = 10.8310 (15) ŵ = 0.08 mm1
α = 94.276 (2)°T = 293 K
β = 99.313 (2)°Block, colourless
γ = 105.773 (2)°0.32 × 0.24 × 0.21 mm
V = 717.72 (17) Å3

Data collection

Bruker APEX CCD diffractometer2748 independent reflections
Radiation source: fine-focus sealed tube2213 reflections with I > 2σ(I)
graphiteRint = 0.012
ω scansθmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −6→9
Tmin = 0.981, Tmax = 0.986k = −11→11
4053 measured reflectionsl = −13→13

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.119w = 1/[σ2(Fo2) + (0.0561P)2 + 0.1075P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2748 reflectionsΔρmax = 0.15 e Å3
185 parametersΔρmin = −0.15 e Å3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.054 (6)

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
C10.4980 (2)0.72180 (15)0.70564 (13)0.0477 (4)
C20.4788 (2)0.72747 (17)0.83128 (14)0.0511 (4)
H20.52890.66800.88320.061*
C30.3862 (2)0.82028 (18)0.87980 (16)0.0603 (4)
H30.37620.82460.96440.072*
C40.3088 (3)0.9062 (2)0.8034 (2)0.0735 (5)
H40.24630.96890.83610.088*
C50.3235 (3)0.8996 (2)0.6782 (2)0.0811 (6)
H50.26910.95690.62630.097*
C60.4180 (3)0.8089 (2)0.62925 (16)0.0658 (5)
H60.42830.80590.54470.079*
C70.6119 (2)0.63374 (16)0.65224 (13)0.0498 (4)
C80.6665 (2)0.51699 (16)0.72240 (13)0.0488 (4)
C90.8739 (2)0.5593 (2)0.78679 (19)0.0733 (5)
H9A0.95460.65580.77730.088*
H9B0.90380.52580.86800.088*
C100.8063 (3)0.4471 (2)0.67465 (19)0.0736 (5)
H10A0.79510.34500.68740.088*
H10B0.84590.47490.59670.088*
C110.5257 (2)0.41812 (16)0.78762 (13)0.0471 (4)
C120.1879 (2)0.26815 (15)0.74941 (13)0.0455 (3)
C130.1551 (2)0.27890 (19)0.87138 (15)0.0591 (4)
H130.23980.35000.93330.071*
C14−0.0041 (3)0.1833 (2)0.90016 (17)0.0742 (5)
H14−0.02520.18930.98240.089*
C15−0.1321 (3)0.0793 (2)0.80958 (19)0.0748 (5)
H15−0.23860.01480.83030.090*
C16−0.1014 (3)0.07135 (19)0.68809 (17)0.0661 (5)
H16−0.18870.00210.62600.079*
C170.0577 (2)0.16516 (16)0.65724 (15)0.0525 (4)
H170.07750.15920.57460.063*
O10.67064 (19)0.66389 (14)0.55579 (10)0.0730 (4)
O20.56848 (17)0.38898 (14)0.89348 (11)0.0682 (4)
N10.34958 (18)0.36333 (14)0.71454 (11)0.0503 (3)
H1N0.338 (3)0.368 (2)0.6331 (14)0.076*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0472 (8)0.0443 (8)0.0446 (8)0.0012 (6)0.0084 (6)0.0072 (6)
C20.0540 (9)0.0509 (8)0.0491 (8)0.0119 (7)0.0149 (7)0.0123 (7)
C30.0634 (10)0.0598 (10)0.0608 (10)0.0154 (8)0.0239 (8)0.0097 (8)
C40.0724 (12)0.0700 (12)0.0874 (14)0.0306 (10)0.0227 (10)0.0127 (10)
C50.0869 (14)0.0849 (14)0.0832 (14)0.0441 (12)0.0096 (11)0.0250 (11)
C60.0737 (12)0.0677 (11)0.0518 (9)0.0153 (9)0.0059 (8)0.0150 (8)
C70.0493 (8)0.0519 (8)0.0394 (7)−0.0013 (7)0.0113 (6)0.0034 (6)
C80.0442 (8)0.0519 (8)0.0472 (8)0.0079 (6)0.0127 (6)0.0010 (6)
C90.0484 (10)0.0856 (13)0.0772 (12)0.0084 (9)0.0073 (9)0.0070 (10)
C100.0663 (12)0.0811 (13)0.0827 (13)0.0263 (10)0.0321 (10)0.0088 (10)
C110.0494 (9)0.0471 (8)0.0447 (8)0.0116 (7)0.0118 (6)0.0066 (6)
C120.0470 (8)0.0430 (7)0.0479 (8)0.0111 (6)0.0141 (6)0.0101 (6)
C130.0560 (10)0.0667 (10)0.0486 (9)0.0058 (8)0.0153 (7)0.0028 (7)
C140.0724 (12)0.0884 (13)0.0582 (10)0.0057 (10)0.0307 (9)0.0116 (9)
C150.0653 (11)0.0684 (12)0.0818 (13)−0.0052 (9)0.0304 (10)0.0107 (10)
C160.0602 (10)0.0549 (10)0.0724 (11)−0.0010 (8)0.0165 (9)−0.0017 (8)
C170.0556 (9)0.0496 (8)0.0514 (8)0.0108 (7)0.0156 (7)0.0046 (7)
O10.0927 (9)0.0769 (8)0.0522 (7)0.0144 (7)0.0360 (6)0.0146 (6)
O20.0616 (7)0.0863 (9)0.0541 (7)0.0149 (6)0.0070 (5)0.0249 (6)
N10.0510 (7)0.0538 (7)0.0413 (7)0.0039 (6)0.0123 (6)0.0091 (6)

Geometric parameters (Å, °)

C1—C61.388 (2)C9—H9B0.970
C1—C21.390 (2)C10—H10A0.970
C1—C71.488 (2)C10—H10B0.970
C2—C31.378 (2)C11—O21.2118 (17)
C2—H20.930C11—N11.3566 (19)
C3—C41.370 (3)C12—C131.383 (2)
C3—H30.930C12—C171.383 (2)
C4—C51.376 (3)C12—N11.4161 (18)
C4—H40.930C13—C141.376 (2)
C5—C61.375 (3)C13—H130.930
C5—H50.930C14—C151.372 (3)
C6—H60.930C14—H140.930
C7—O11.2196 (16)C15—C161.371 (2)
C7—C81.495 (2)C15—H150.930
C8—C111.5080 (19)C16—C171.378 (2)
C8—C101.510 (2)C16—H160.930
C8—C91.514 (2)C17—H170.930
C9—C101.476 (3)N1—H1N0.879 (14)
C9—H9A0.970
C6—C1—C2118.62 (15)H9A—C9—H9B114.8
C6—C1—C7118.78 (14)C9—C10—C860.95 (11)
C2—C1—C7122.46 (13)C9—C10—H10A117.7
C3—C2—C1120.68 (15)C8—C10—H10A117.7
C3—C2—H2119.7C9—C10—H10B117.7
C1—C2—H2119.7C8—C10—H10B117.7
C4—C3—C2120.01 (16)H10A—C10—H10B114.8
C4—C3—H3120.0O2—C11—N1124.09 (13)
C2—C3—H3120.0O2—C11—C8122.85 (14)
C3—C4—C5119.93 (18)N1—C11—C8113.04 (12)
C3—C4—H4120.0C13—C12—C17119.77 (14)
C5—C4—H4120.0C13—C12—N1121.74 (14)
C6—C5—C4120.52 (17)C17—C12—N1118.46 (13)
C6—C5—H5119.7C14—C13—C12119.32 (16)
C4—C5—H5119.7C14—C13—H13120.3
C5—C6—C1120.21 (17)C12—C13—H13120.3
C5—C6—H6119.9C15—C14—C13121.14 (16)
C1—C6—H6119.9C15—C14—H14119.4
O1—C7—C1119.69 (14)C13—C14—H14119.4
O1—C7—C8120.33 (14)C14—C15—C16119.35 (16)
C1—C7—C8119.80 (12)C14—C15—H15120.3
C7—C8—C11120.13 (13)C16—C15—H15120.3
C7—C8—C10117.63 (13)C15—C16—C17120.55 (16)
C11—C8—C10114.96 (13)C15—C16—H16119.7
C7—C8—C9114.24 (13)C17—C16—H16119.7
C11—C8—C9116.43 (14)C16—C17—C12119.85 (15)
C10—C8—C958.41 (12)C16—C17—H17120.1
C10—C9—C860.64 (11)C12—C17—H17120.1
C10—C9—H9A117.7C11—N1—C12126.26 (12)
C8—C9—H9A117.7C11—N1—H1N118.1 (12)
C10—C9—H9B117.7C12—N1—H1N114.0 (12)
C8—C9—H9B117.7
C6—C1—C2—C3−1.6 (2)C7—C8—C10—C9102.84 (16)
C7—C1—C2—C3174.30 (14)C11—C8—C10—C9−106.87 (16)
C1—C2—C3—C41.2 (3)C7—C8—C11—O2−135.19 (16)
C2—C3—C4—C50.1 (3)C10—C8—C11—O275.3 (2)
C3—C4—C5—C6−1.0 (3)C9—C8—C11—O29.8 (2)
C4—C5—C6—C10.6 (3)C7—C8—C11—N146.30 (18)
C2—C1—C6—C50.6 (3)C10—C8—C11—N1−103.20 (16)
C7—C1—C6—C5−175.38 (16)C9—C8—C11—N1−168.75 (14)
C6—C1—C7—O117.1 (2)C17—C12—C13—C142.1 (3)
C2—C1—C7—O1−158.80 (15)N1—C12—C13—C14−179.83 (16)
C6—C1—C7—C8−167.79 (14)C12—C13—C14—C15−1.1 (3)
C2—C1—C7—C816.4 (2)C13—C14—C15—C16−0.5 (3)
O1—C7—C8—C11−144.49 (15)C14—C15—C16—C171.0 (3)
C1—C7—C8—C1140.38 (19)C15—C16—C17—C120.1 (3)
O1—C7—C8—C104.2 (2)C13—C12—C17—C16−1.7 (2)
C1—C7—C8—C10−170.91 (14)N1—C12—C17—C16−179.76 (14)
O1—C7—C8—C969.84 (19)O2—C11—N1—C121.7 (2)
C1—C7—C8—C9−105.29 (16)C8—C11—N1—C12−179.78 (13)
C7—C8—C9—C10−108.67 (15)C13—C12—N1—C1134.8 (2)
C11—C8—C9—C10104.33 (16)C17—C12—N1—C11−147.15 (15)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.88 (1)2.03 (1)2.896 (1)167 (1)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BI2312).

References

  • Bruker (1997). SAINT and SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zhang, Z., Zhang, Q., Sun, S., Xiong, T. & Liu, Q. (2007). Angew. Chem. Int. Ed.46, 1726–1729. [PubMed]

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