3-(3-Cyano-phen-yl)-N-phenyl-oxirane-2-carboxamide.

In the title compound, C(16)H(12)N(2)O(2), both terminal benzene rings are located at the same side of the central epoxide ring, showing a cis conformation. The epoxide ring makes dihedral angles of 76.59 (10) and 62.40 (11)° with the phenyl and cyano-phenyl rings, respectively. Inter-molecular N-H⋯O and weak C-H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For the use of epoxide-containing compounds as building blocks in synthesis, see: Meth-Cohn & Chen (1999 ▶); Porter & Skidmore (2000 ▶); Righi et al. (1996 ▶); Thijs et al. (1990 ▶). For related structures, see: Chen & Kang (2009a ▶,b ▶); He (2009 ▶); He et al. (2009 ▶).

Experimental

Crystal data

C16H12N2O2

M = 264.28

Orthorhombic,

a = 5.459 (2) Å

b = 11.141 (7) Å

c = 21.844 (5) Å

V = 1328.6 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 291 K

0.36 × 0.32 × 0.26 mm

Data collection

Oxford Diffraction Gemini S Ultra diffractometer

9766 measured reflections

2078 independent reflections

1378 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.072

S = 1.00

2078 reflections

181 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810037475/xu5025sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810037475/xu5025Isup2.hkl

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

C16H12N2O2	Dx = 1.321 Mg m−3
Mr = 264.28	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 3256 reflections
a = 5.459 (2) Å	θ = 3.3–29.0°
b = 11.141 (7) Å	µ = 0.09 mm−1
c = 21.844 (5) Å	T = 291 K
V = 1328.6 (10) Å3	Block, colorless
Z = 4	0.36 × 0.32 × 0.26 mm
F(000) = 552

Oxford Diffraction Gemini S Ultra diffractometer	1378 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.042
graphite	θmax = 29.2°, θmin = 3.3°
Detector resolution: 15.9149 pixels mm-1	h = −7→3
ω scans	k = −15→15
9766 measured reflections	l = −29→27
2078 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0322P)2] where P = (Fo2 + 2Fc2)/3
2078 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.14 e Å−3
1 restraint	Δρmin = −0.18 e Å−3

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
O2	0.2729 (2)	1.02915 (12)	0.76684 (6)	0.0522 (4)
O1	−0.2382 (2)	0.87594 (13)	0.69492 (6)	0.0540 (4)
N1	0.1739 (3)	0.86142 (13)	0.67637 (7)	0.0416 (4)
H4	0.3135	0.8914	0.6864	0.050*
C4	0.1740 (3)	0.76926 (15)	0.63124 (8)	0.0350 (4)
C3	0.3670 (3)	0.68860 (17)	0.63104 (9)	0.0430 (5)
H3	0.4906	0.6946	0.6602	0.052*
C6	−0.0019 (4)	0.67021 (17)	0.54450 (8)	0.0453 (5)
H6	−0.1252	0.6639	0.5153	0.054*
C10	0.1794 (3)	0.85668 (17)	0.83606 (8)	0.0389 (4)
C2	0.3746 (4)	0.59914 (18)	0.58733 (9)	0.0481 (5)
H2	0.5047	0.5453	0.5866	0.058*
C1	0.1884 (4)	0.58954 (18)	0.54452 (9)	0.0446 (5)
H1	0.1923	0.5282	0.5157	0.053*
C9	0.1163 (3)	0.97731 (17)	0.81328 (9)	0.0429 (5)
H9	0.0615	1.0337	0.8449	0.051*
C5	−0.0106 (3)	0.76092 (17)	0.58780 (8)	0.0423 (5)
H5	−0.1391	0.8157	0.5878	0.051*
C8	0.0212 (4)	1.00240 (16)	0.75099 (9)	0.0442 (4)
H8	−0.0867	1.0724	0.7479	0.053*
C15	0.0302 (3)	0.80528 (19)	0.88008 (9)	0.0470 (5)
H15	−0.1075	0.8466	0.8937	0.056*
C11	0.3875 (4)	0.79694 (18)	0.81664 (9)	0.0491 (5)
H11	0.4905	0.8318	0.7878	0.059*
C14	0.0830 (3)	0.6931 (2)	0.90422 (9)	0.0504 (5)
C7	−0.0260 (4)	0.90608 (17)	0.70496 (8)	0.0397 (4)
C12	0.4420 (4)	0.68306 (19)	0.84092 (10)	0.0567 (6)
H12	0.5803	0.6418	0.8277	0.068*
C16	−0.0707 (4)	0.6410 (2)	0.94879 (11)	0.0735 (7)
C13	0.2917 (4)	0.6330 (2)	0.88396 (10)	0.0552 (5)
H13	0.3292	0.5579	0.8999	0.066*
N2	−0.1971 (5)	0.5975 (2)	0.98491 (12)	0.1095 (10)

	U11	U22	U33	U12	U13	U23
O2	0.0630 (9)	0.0466 (8)	0.0469 (8)	−0.0178 (7)	0.0058 (7)	−0.0050 (6)
O1	0.0430 (7)	0.0614 (10)	0.0576 (9)	−0.0045 (7)	0.0059 (7)	−0.0130 (7)
N1	0.0377 (8)	0.0450 (9)	0.0421 (9)	−0.0068 (7)	0.0002 (7)	−0.0096 (8)
C4	0.0367 (9)	0.0361 (10)	0.0323 (10)	−0.0069 (8)	0.0031 (8)	0.0022 (8)
C3	0.0356 (9)	0.0477 (12)	0.0457 (11)	−0.0025 (9)	−0.0070 (9)	−0.0043 (10)
C6	0.0479 (11)	0.0535 (12)	0.0344 (10)	−0.0047 (10)	−0.0047 (9)	−0.0005 (10)
C10	0.0424 (10)	0.0417 (10)	0.0327 (10)	−0.0036 (9)	−0.0020 (8)	−0.0081 (9)
C2	0.0424 (10)	0.0458 (12)	0.0561 (13)	0.0033 (10)	0.0024 (10)	−0.0049 (10)
C1	0.0531 (12)	0.0429 (11)	0.0376 (11)	−0.0061 (10)	0.0074 (9)	−0.0057 (9)
C9	0.0511 (10)	0.0401 (11)	0.0375 (11)	−0.0015 (9)	0.0085 (9)	−0.0064 (9)
C5	0.0446 (10)	0.0454 (11)	0.0370 (11)	0.0053 (10)	−0.0027 (9)	0.0009 (9)
C8	0.0537 (11)	0.0371 (10)	0.0418 (11)	−0.0009 (9)	0.0034 (9)	−0.0023 (9)
C15	0.0455 (10)	0.0526 (12)	0.0429 (12)	0.0048 (10)	0.0038 (10)	−0.0010 (10)
C11	0.0448 (10)	0.0616 (14)	0.0408 (11)	0.0010 (10)	0.0056 (9)	−0.0048 (11)
C14	0.0535 (12)	0.0542 (13)	0.0435 (12)	0.0022 (11)	−0.0021 (10)	0.0068 (11)
C7	0.0475 (11)	0.0356 (10)	0.0359 (10)	−0.0027 (9)	0.0026 (9)	0.0031 (9)
C12	0.0561 (13)	0.0611 (15)	0.0529 (13)	0.0186 (11)	0.0003 (11)	−0.0095 (12)
C16	0.0719 (16)	0.0759 (16)	0.0726 (17)	0.0088 (14)	0.0115 (14)	0.0317 (15)
C13	0.0690 (14)	0.0470 (12)	0.0496 (12)	0.0069 (12)	−0.0081 (11)	−0.0007 (10)
N2	0.1022 (19)	0.111 (2)	0.115 (2)	0.0091 (16)	0.0281 (17)	0.0571 (17)

O2—C9	1.447 (2)	C2—H2	0.9300
O2—C8	1.448 (2)	C1—H1	0.9300
O1—C7	1.226 (2)	C9—C8	1.483 (3)
N1—C7	1.352 (2)	C9—H9	0.9800
N1—C4	1.423 (2)	C5—H5	0.9300
N1—H4	0.8600	C8—C7	1.493 (3)
C4—C3	1.384 (2)	C8—H8	0.9800
C4—C5	1.387 (2)	C15—C14	1.387 (3)
C3—C2	1.381 (3)	C15—H15	0.9300
C3—H3	0.9300	C11—C12	1.407 (2)
C6—C1	1.374 (3)	C11—H11	0.9300
C6—C5	1.385 (3)	C14—C13	1.394 (3)
C6—H6	0.9300	C14—C16	1.411 (2)
C10—C11	1.383 (3)	C12—C13	1.367 (3)
C10—C15	1.384 (2)	C12—H12	0.9300
C10—C9	1.474 (3)	C16—N2	1.155 (3)
C2—C1	1.385 (3)	C13—H13	0.9300
C9—O2—C8	61.64 (11)	C6—C5—C4	119.40 (18)
C7—N1—C4	125.86 (15)	C6—C5—H5	120.3
C7—N1—H4	117.1	C4—C5—H5	120.3
C4—N1—H4	117.1	O2—C8—C9	59.14 (12)
C3—C4—C5	120.47 (17)	O2—C8—C7	118.21 (15)
C3—C4—N1	118.09 (16)	C9—C8—C7	122.89 (16)
C5—C4—N1	121.43 (16)	O2—C8—H8	115.0
C2—C3—C4	119.58 (17)	C9—C8—H8	115.0
C2—C3—H3	120.2	C7—C8—H8	115.0
C4—C3—H3	120.2	C10—C15—C14	120.97 (18)
C1—C6—C5	120.21 (18)	C10—C15—H15	119.5
C1—C6—H6	119.9	C14—C15—H15	119.5
C5—C6—H6	119.9	C10—C11—C12	119.47 (18)
C11—C10—C15	119.82 (18)	C10—C11—H11	120.3
C11—C10—C9	121.80 (17)	C12—C11—H11	120.3
C15—C10—C9	118.31 (17)	C15—C14—C13	118.82 (19)
C3—C2—C1	120.03 (18)	C15—C14—C16	120.7 (2)
C3—C2—H2	120.0	C13—C14—C16	120.5 (2)
C1—C2—H2	120.0	O1—C7—N1	125.40 (18)
C6—C1—C2	120.31 (17)	O1—C7—C8	118.70 (17)
C6—C1—H1	119.8	N1—C7—C8	115.87 (16)
C2—C1—H1	119.8	C13—C12—C11	120.00 (19)
O2—C9—C10	117.57 (16)	C13—C12—H12	120.0
O2—C9—C8	59.22 (12)	C11—C12—H12	120.0
C10—C9—C8	124.29 (16)	N2—C16—C14	179.4 (3)
O2—C9—H9	114.7	C12—C13—C14	120.9 (2)
C10—C9—H9	114.7	C12—C13—H13	119.5
C8—C9—H9	114.7	C14—C13—H13	119.5
C7—N1—C4—C3	−143.99 (18)	C10—C9—C8—C7	1.4 (3)
C7—N1—C4—C5	37.1 (3)	C11—C10—C15—C14	−1.4 (3)
C5—C4—C3—C2	−0.2 (3)	C9—C10—C15—C14	−178.62 (18)
N1—C4—C3—C2	−179.08 (17)	C15—C10—C11—C12	1.5 (3)
C4—C3—C2—C1	−0.8 (3)	C9—C10—C11—C12	178.54 (18)
C5—C6—C1—C2	−0.8 (3)	C10—C15—C14—C13	0.8 (3)
C3—C2—C1—C6	1.3 (3)	C10—C15—C14—C16	−179.6 (2)
C8—O2—C9—C10	115.39 (18)	C4—N1—C7—O1	−2.2 (3)
C11—C10—C9—O2	3.5 (3)	C4—N1—C7—C8	179.70 (15)
C15—C10—C9—O2	−179.39 (15)	O2—C8—C7—O1	174.09 (18)
C11—C10—C9—C8	73.5 (3)	C9—C8—C7—O1	104.4 (2)
C15—C10—C9—C8	−109.4 (2)	O2—C8—C7—N1	−7.6 (2)
C1—C6—C5—C4	−0.2 (3)	C9—C8—C7—N1	−77.4 (2)
C3—C4—C5—C6	0.7 (3)	C10—C11—C12—C13	−0.9 (3)
N1—C4—C5—C6	179.55 (16)	C11—C12—C13—C14	0.3 (3)
C9—O2—C8—C7	−113.41 (19)	C15—C14—C13—C12	−0.2 (3)
C10—C9—C8—O2	−104.2 (2)	C16—C14—C13—C12	−179.8 (2)
O2—C9—C8—C7	105.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H4···O1i	0.86	2.46	3.239 (3)	151 (1)
C11—H11···O1i	0.93	2.56	3.467 (3)	165 (1)
C12—H12···O2ii	0.93	2.55	3.302 (3)	139 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H4⋯O1i	0.86	2.46	3.239 (3)	151 (1)
C11—H11⋯O1i	0.93	2.56	3.467 (3)	165 (1)
C12—H12⋯O2ii	0.93	2.55	3.302 (3)	139 (1)

Symmetry codes: (i) ; (ii) .