1-Benzoyl-N-phenyl­cyclo­propane­carboxamide

Li, W.-L.; Zhu, Z.-G.

doi:10.1107/S1600536808034077

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2179

doi:10.1107/S1600536808034077

Open

access

1-Benzoyl-N-phenylcyclopropanecarboxamide

Wen-Liang Li ^a and Zhi-Guo Zhu ^a ^*

^aExperimental Center of Medicine, Jilin Medical College, Jilin 132013, People's Republic of China
^*Correspondence e-mail: wenliangli.chem@gmail.com

(Received 14 October 2008; accepted 18 October 2008; online 25 October 2008)

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 ).

Experimental

Crystal data

C₁₇H₁₅NO₂
M_r = 265.30
Triclinic, $[P \overline 1]$
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 ) 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[F² > 2σ(F²)] = 0.044
wR(F²) = 0.119
S = 1.04
2748 reflections
185 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.879 (14)	2.03 (1)	2.896 (1)	167.0 (1)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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.

Supporting information

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

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

checkCIF report

Comment top

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)°.

Related literature top

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

Experimental top

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.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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

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

1-Benzoyl-N-phenylcyclopropanecarboxamide top

Crystal data top

C₁₇H₁₅NO₂	Z = 2
M_r = 265.30	F(000) = 280
Triclinic, P1	D_x = 1.228 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 7.424 (1) Å	Cell parameters from 2748 reflections
b = 9.4730 (13) Å	θ = 1.9–26.0°
c = 10.8310 (15) Å	µ = 0.08 mm⁻¹
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 top

Bruker APEX CCD diffractometer	2748 independent reflections
Radiation source: fine-focus sealed tube	2213 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.012
ω scans	θ_max = 26.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→9
T_min = 0.981, T_max = 0.986	k = −11→11
4053 measured reflections	l = −13→13

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.119	w = 1/[σ²(F_o²) + (0.0561P)² + 0.1075P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2748 reflections	Δρ_max = 0.15 e Å⁻³
185 parameters	Δρ_min = −0.15 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.054 (6)

Crystal data top

C₁₇H₁₅NO₂	γ = 105.773 (2)°
M_r = 265.30	V = 717.72 (17) Å³
Triclinic, P1	Z = 2
a = 7.424 (1) Å	Mo Kα radiation
b = 9.4730 (13) Å	µ = 0.08 mm⁻¹
c = 10.8310 (15) Å	T = 293 K
α = 94.276 (2)°	0.32 × 0.24 × 0.21 mm
β = 99.313 (2)°

Data collection top

Bruker APEX CCD diffractometer	2748 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2213 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.986	R_int = 0.012
4053 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	1 restraint
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.15 e Å⁻³
2748 reflections	Δρ_min = −0.15 e Å⁻³
185 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

	x	y	z	U_iso*/U_eq
C1	0.4980 (2)	0.72180 (15)	0.70564 (13)	0.0477 (4)
C2	0.4788 (2)	0.72747 (17)	0.83128 (14)	0.0511 (4)
H2	0.5289	0.6680	0.8832	0.061*
C3	0.3862 (2)	0.82028 (18)	0.87980 (16)	0.0603 (4)
H3	0.3762	0.8246	0.9644	0.072*
C4	0.3088 (3)	0.9062 (2)	0.8034 (2)	0.0735 (5)
H4	0.2463	0.9689	0.8361	0.088*
C5	0.3235 (3)	0.8996 (2)	0.6782 (2)	0.0811 (6)
H5	0.2691	0.9569	0.6263	0.097*
C6	0.4180 (3)	0.8089 (2)	0.62925 (16)	0.0658 (5)
H6	0.4283	0.8059	0.5447	0.079*
C7	0.6119 (2)	0.63374 (16)	0.65224 (13)	0.0498 (4)
C8	0.6665 (2)	0.51699 (16)	0.72240 (13)	0.0488 (4)
C9	0.8739 (2)	0.5593 (2)	0.78679 (19)	0.0733 (5)
H9A	0.9546	0.6558	0.7773	0.088*
H9B	0.9038	0.5258	0.8680	0.088*
C10	0.8063 (3)	0.4471 (2)	0.67465 (19)	0.0736 (5)
H10A	0.7951	0.3450	0.6874	0.088*
H10B	0.8459	0.4749	0.5967	0.088*
C11	0.5257 (2)	0.41812 (16)	0.78762 (13)	0.0471 (4)
C12	0.1879 (2)	0.26815 (15)	0.74941 (13)	0.0455 (3)
C13	0.1551 (2)	0.27890 (19)	0.87138 (15)	0.0591 (4)
H13	0.2398	0.3500	0.9333	0.071*
C14	−0.0041 (3)	0.1833 (2)	0.90016 (17)	0.0742 (5)
H14	−0.0252	0.1893	0.9824	0.089*
C15	−0.1321 (3)	0.0793 (2)	0.80958 (19)	0.0748 (5)
H15	−0.2386	0.0148	0.8303	0.090*
C16	−0.1014 (3)	0.07135 (19)	0.68809 (17)	0.0661 (5)
H16	−0.1887	0.0021	0.6260	0.079*
C17	0.0577 (2)	0.16516 (16)	0.65724 (15)	0.0525 (4)
H17	0.0775	0.1592	0.5746	0.063*
O1	0.67064 (19)	0.66389 (14)	0.55579 (10)	0.0730 (4)
O2	0.56848 (17)	0.38898 (14)	0.89348 (11)	0.0682 (4)
N1	0.34958 (18)	0.36333 (14)	0.71454 (11)	0.0503 (3)
H1N	0.338 (3)	0.368 (2)	0.6331 (14)	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0472 (8)	0.0443 (8)	0.0446 (8)	0.0012 (6)	0.0084 (6)	0.0072 (6)
C2	0.0540 (9)	0.0509 (8)	0.0491 (8)	0.0119 (7)	0.0149 (7)	0.0123 (7)
C3	0.0634 (10)	0.0598 (10)	0.0608 (10)	0.0154 (8)	0.0239 (8)	0.0097 (8)
C4	0.0724 (12)	0.0700 (12)	0.0874 (14)	0.0306 (10)	0.0227 (10)	0.0127 (10)
C5	0.0869 (14)	0.0849 (14)	0.0832 (14)	0.0441 (12)	0.0096 (11)	0.0250 (11)
C6	0.0737 (12)	0.0677 (11)	0.0518 (9)	0.0153 (9)	0.0059 (8)	0.0150 (8)
C7	0.0493 (8)	0.0519 (8)	0.0394 (7)	−0.0013 (7)	0.0113 (6)	0.0034 (6)
C8	0.0442 (8)	0.0519 (8)	0.0472 (8)	0.0079 (6)	0.0127 (6)	0.0010 (6)
C9	0.0484 (10)	0.0856 (13)	0.0772 (12)	0.0084 (9)	0.0073 (9)	0.0070 (10)
C10	0.0663 (12)	0.0811 (13)	0.0827 (13)	0.0263 (10)	0.0321 (10)	0.0088 (10)
C11	0.0494 (9)	0.0471 (8)	0.0447 (8)	0.0116 (7)	0.0118 (6)	0.0066 (6)
C12	0.0470 (8)	0.0430 (7)	0.0479 (8)	0.0111 (6)	0.0141 (6)	0.0101 (6)
C13	0.0560 (10)	0.0667 (10)	0.0486 (9)	0.0058 (8)	0.0153 (7)	0.0028 (7)
C14	0.0724 (12)	0.0884 (13)	0.0582 (10)	0.0057 (10)	0.0307 (9)	0.0116 (9)
C15	0.0653 (11)	0.0684 (12)	0.0818 (13)	−0.0052 (9)	0.0304 (10)	0.0107 (10)
C16	0.0602 (10)	0.0549 (10)	0.0724 (11)	−0.0010 (8)	0.0165 (9)	−0.0017 (8)
C17	0.0556 (9)	0.0496 (8)	0.0514 (8)	0.0108 (7)	0.0156 (7)	0.0046 (7)
O1	0.0927 (9)	0.0769 (8)	0.0522 (7)	0.0144 (7)	0.0360 (6)	0.0146 (6)
O2	0.0616 (7)	0.0863 (9)	0.0541 (7)	0.0149 (6)	0.0070 (5)	0.0249 (6)
N1	0.0510 (7)	0.0538 (7)	0.0413 (7)	0.0039 (6)	0.0123 (6)	0.0091 (6)

Geometric parameters (Å, º) top

C1—C6	1.388 (2)	C9—H9B	0.970
C1—C2	1.390 (2)	C10—H10A	0.970
C1—C7	1.488 (2)	C10—H10B	0.970
C2—C3	1.378 (2)	C11—O2	1.2118 (17)
C2—H2	0.930	C11—N1	1.3566 (19)
C3—C4	1.370 (3)	C12—C13	1.383 (2)
C3—H3	0.930	C12—C17	1.383 (2)
C4—C5	1.376 (3)	C12—N1	1.4161 (18)
C4—H4	0.930	C13—C14	1.376 (2)
C5—C6	1.375 (3)	C13—H13	0.930
C5—H5	0.930	C14—C15	1.372 (3)
C6—H6	0.930	C14—H14	0.930
C7—O1	1.2196 (16)	C15—C16	1.371 (2)
C7—C8	1.495 (2)	C15—H15	0.930
C8—C11	1.5080 (19)	C16—C17	1.378 (2)
C8—C10	1.510 (2)	C16—H16	0.930
C8—C9	1.514 (2)	C17—H17	0.930
C9—C10	1.476 (3)	N1—H1N	0.879 (14)
C9—H9A	0.970

C6—C1—C2	118.62 (15)	H9A—C9—H9B	114.8
C6—C1—C7	118.78 (14)	C9—C10—C8	60.95 (11)
C2—C1—C7	122.46 (13)	C9—C10—H10A	117.7
C3—C2—C1	120.68 (15)	C8—C10—H10A	117.7
C3—C2—H2	119.7	C9—C10—H10B	117.7
C1—C2—H2	119.7	C8—C10—H10B	117.7
C4—C3—C2	120.01 (16)	H10A—C10—H10B	114.8
C4—C3—H3	120.0	O2—C11—N1	124.09 (13)
C2—C3—H3	120.0	O2—C11—C8	122.85 (14)
C3—C4—C5	119.93 (18)	N1—C11—C8	113.04 (12)
C3—C4—H4	120.0	C13—C12—C17	119.77 (14)
C5—C4—H4	120.0	C13—C12—N1	121.74 (14)
C6—C5—C4	120.52 (17)	C17—C12—N1	118.46 (13)
C6—C5—H5	119.7	C14—C13—C12	119.32 (16)
C4—C5—H5	119.7	C14—C13—H13	120.3
C5—C6—C1	120.21 (17)	C12—C13—H13	120.3
C5—C6—H6	119.9	C15—C14—C13	121.14 (16)
C1—C6—H6	119.9	C15—C14—H14	119.4
O1—C7—C1	119.69 (14)	C13—C14—H14	119.4
O1—C7—C8	120.33 (14)	C14—C15—C16	119.35 (16)
C1—C7—C8	119.80 (12)	C14—C15—H15	120.3
C7—C8—C11	120.13 (13)	C16—C15—H15	120.3
C7—C8—C10	117.63 (13)	C15—C16—C17	120.55 (16)
C11—C8—C10	114.96 (13)	C15—C16—H16	119.7
C7—C8—C9	114.24 (13)	C17—C16—H16	119.7
C11—C8—C9	116.43 (14)	C16—C17—C12	119.85 (15)
C10—C8—C9	58.41 (12)	C16—C17—H17	120.1
C10—C9—C8	60.64 (11)	C12—C17—H17	120.1
C10—C9—H9A	117.7	C11—N1—C12	126.26 (12)
C8—C9—H9A	117.7	C11—N1—H1N	118.1 (12)
C10—C9—H9B	117.7	C12—N1—H1N	114.0 (12)
C8—C9—H9B	117.7

C6—C1—C2—C3	−1.6 (2)	C7—C8—C10—C9	102.84 (16)
C7—C1—C2—C3	174.30 (14)	C11—C8—C10—C9	−106.87 (16)
C1—C2—C3—C4	1.2 (3)	C7—C8—C11—O2	−135.19 (16)
C2—C3—C4—C5	0.1 (3)	C10—C8—C11—O2	75.3 (2)
C3—C4—C5—C6	−1.0 (3)	C9—C8—C11—O2	9.8 (2)
C4—C5—C6—C1	0.6 (3)	C7—C8—C11—N1	46.30 (18)
C2—C1—C6—C5	0.6 (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—O1	17.1 (2)	C17—C12—C13—C14	2.1 (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—C8	16.4 (2)	C13—C14—C15—C16	−0.5 (3)
O1—C7—C8—C11	−144.49 (15)	C14—C15—C16—C17	1.0 (3)
C1—C7—C8—C11	40.38 (19)	C15—C16—C17—C12	0.1 (3)
O1—C7—C8—C10	4.2 (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—C9	69.84 (19)	O2—C11—N1—C12	1.7 (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—C11	34.8 (2)
C11—C8—C9—C10	104.33 (16)	C17—C12—N1—C11	−147.15 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.88 (1)	2.03 (1)	2.896 (1)	167 (1)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅NO₂
M_r	265.30
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.424 (1), 9.4730 (13), 10.8310 (15)
α, β, γ (°)	94.276 (2), 99.313 (2), 105.773 (2)
V (Å³)	717.72 (17)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.32 × 0.24 × 0.21

Data collection
Diffractometer	Bruker APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.981, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	4053, 2748, 2213
R_int	0.012
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.119, 1.04
No. of reflections	2748
No. of parameters	185
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.15

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.879 (14)	2.03 (1)	2.896 (1)	167.0 (1)

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

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

References

Bruker (1997). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, Z., Zhang, Q., Sun, S., Xiong, T. & Liu, Q. (2007). Angew. Chem. Int. Ed. 46, 1726–1729. Web of Science CSD CrossRef CAS Google Scholar