1-Benzoyl-N-phenyl-cyclo-propane-carboxamide.

The title compound, C(17)H(15)NO(2), was synthesized by reaction of 1,2-dibromo-ethane with 1-benzoyl-N-phenyl-cyclo-propane-carboxamide and K(2)CO(3) in dimethyl-formamide. The mol-ecule 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 mol-ecules into dimers about centres of inversion.

Related literature

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

Experimental

Crystal data

C17H15NO2

M = 265.30

Triclinic,

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[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 ▶); 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.

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

C17H15NO2	Z = 2
Mr = 265.30	F(000) = 280
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0561P)2 + 0.1075P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2748 reflections	Δρmax = 0.15 e Å−3
185 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)

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) .