(2R,3R)-3-(2-Chloro-phen-yl)-N-phenyl-oxirane-2-carboxamide.

In the title compound, C(15)H(12)ClNO(2), the two benzene rings adopt a syn configuration with respect to the ep-oxy ring; the dihedral angles between the ep-oxy ring and the two benzene rings are 59.71 (16) and 67.58 (15)°. There is a weak intra-molecular N-H⋯O bond, which may help to establish the conformation. In the crystal, the mol-ecules are linked into a chain parallel to the b axis through inter-molecular N-H⋯O hydrogen bonds.

Related literature

For the use of epoxide-containing compounds as building blocks in the n class="Gene">synthesis of biologically active compounds, see: Flisak et al. (1993 ▶); Porter & Skidmore (2000 ▶); Shing et al. (2006 ▶); Watanabe et al. (1998 ▶); Zhu & Espenson (1995 ▶). For the isostructuralbromo compound, 3-(2-bromo­phen­yl)-N-phenyl­oxirane-2-carboxamide, see: He et al. (2009 ▶). For related structures, see: He (2009 ▶); He & Chen (2009 ▶).

Experimental

Crystal data

C15H12ClNO2

M = 273.71

Orthorhombic,

a = 6.6610 (1) Å

b = 10.0343 (2) Å

c = 20.2433 (3) Å

V = 1353.03 (4) Å3

Z = 4

Cu Kα radiation

μ = 2.48 mm−1

T = 295 K

0.36 × 0.32 × 0.30 mm

Data collection

Oxford Diffraction Gemini S Ultra diffractometer

Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2009 ▶) T min = 0.469, T max = 0.524

9086 measured reflections

2373 independent reflections

2100 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.109

S = 1.20

2373 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.26 e Å−3

Absolute structure: Flack (1983 ▶), 864 Friedel pairs

Flack parameter: 0.01 (2)

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: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048442/dn2512sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048442/dn2512Isup2.hkl

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

C15H12ClNO2	F(000) = 568
Mr = 273.71	Dx = 1.344 Mg m−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9390 reflections
a = 6.6610 (1) Å	θ = 4.4–72.1°
b = 10.0343 (2) Å	µ = 2.48 mm−1
c = 20.2433 (3) Å	T = 295 K
V = 1353.03 (4) Å3	Block, colourless
Z = 4	0.36 × 0.32 × 0.30 mm

Oxford Diffraction Gemini S Ultra diffractometer	2373 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	2100 reflections with I > 2σ(I)
mirror	Rint = 0.026
Detector resolution: 15.9149 pixels mm-1	θmax = 70.0°, θmin = 4.4°
ω scans	h = −4→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −12→12
Tmin = 0.469, Tmax = 0.524	l = −24→24
9086 measured reflections

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)] = 0.031	H-atom parameters constrained
wR(F2) = 0.109	w = 1/[σ2(Fo2) + (0.0455P)2 + 0.2775P] where P = (Fo2 + 2Fc2)/3
S = 1.20	(Δ/σ)max < 0.001
2373 reflections	Δρmax = 0.15 e Å−3
172 parameters	Δρmin = −0.26 e Å−3
0 restraints	Absolute structure: Flack (1983), 864 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (2)

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. CrysAlisPro (Oxford Diffraction, 2009)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.4506 (5)	1.0038 (3)	0.44438 (13)	0.0628 (7)
C2	0.2775 (5)	1.0218 (3)	0.48079 (15)	0.0783 (9)
H2	0.2568	1.1009	0.5038	0.094*
C3	0.1355 (6)	0.9220 (4)	0.48286 (16)	0.0815 (9)
H3	0.0200	0.9334	0.5080	0.098*
C4	0.1626 (5)	0.8067 (3)	0.44834 (16)	0.0785 (8)
H4	0.0656	0.7401	0.4495	0.094*
C5	0.3367 (5)	0.7894 (3)	0.41138 (14)	0.0673 (7)
H5	0.3547	0.7109	0.3877	0.081*
C6	0.4835 (4)	0.8867 (2)	0.40921 (12)	0.0559 (6)
C7	0.6754 (4)	0.8661 (3)	0.37349 (13)	0.0602 (6)
H7	0.7957	0.8931	0.3979	0.072*
C8	0.6969 (4)	0.8680 (2)	0.30113 (13)	0.0571 (6)
H8	0.8281	0.8969	0.2845	0.069*
C9	0.5200 (4)	0.9026 (2)	0.25827 (12)	0.0519 (5)
C10	0.2091 (4)	0.8095 (2)	0.20952 (11)	0.0485 (5)
C11	0.0848 (4)	0.7002 (2)	0.21366 (14)	0.0591 (6)
H11	0.1203	0.6288	0.2405	0.071*
C12	−0.0942 (5)	0.6958 (3)	0.17779 (15)	0.0719 (8)
H12	−0.1769	0.6213	0.1803	0.086*
C13	−0.1475 (5)	0.8020 (3)	0.13874 (14)	0.0737 (8)
H13	−0.2655	0.7993	0.1142	0.088*
C14	−0.0262 (5)	0.9114 (3)	0.13617 (14)	0.0734 (8)
H14	−0.0652	0.9840	0.1106	0.088*
C15	0.1546 (5)	0.9176 (3)	0.17082 (13)	0.0618 (6)
H15	0.2366	0.9924	0.1680	0.074*
Cl1	0.63034 (15)	1.12873 (8)	0.44179 (4)	0.0905 (3)
N1	0.3914 (3)	0.80345 (18)	0.24575 (10)	0.0524 (5)
H1	0.4229	0.7267	0.2616	0.063*
O1	0.6959 (3)	0.74497 (17)	0.33669 (10)	0.0666 (5)
O2	0.5063 (3)	1.01692 (16)	0.23815 (11)	0.0732 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0775 (18)	0.0568 (13)	0.0540 (12)	0.0057 (14)	−0.0038 (13)	0.0006 (12)
C2	0.100 (2)	0.0729 (19)	0.0619 (15)	0.0152 (19)	0.0041 (16)	−0.0041 (14)
C3	0.074 (2)	0.098 (2)	0.0730 (17)	0.004 (2)	0.0099 (16)	0.0101 (17)
C4	0.076 (2)	0.082 (2)	0.0773 (18)	−0.0094 (18)	−0.0062 (17)	0.0141 (17)
C5	0.0738 (19)	0.0615 (15)	0.0667 (15)	−0.0019 (15)	−0.0138 (15)	0.0035 (13)
C6	0.0609 (15)	0.0507 (12)	0.0561 (12)	0.0041 (13)	−0.0142 (11)	0.0003 (11)
C7	0.0592 (16)	0.0489 (12)	0.0725 (14)	0.0062 (13)	−0.0135 (12)	−0.0100 (12)
C8	0.0577 (15)	0.0389 (11)	0.0748 (15)	0.0054 (12)	−0.0031 (12)	−0.0085 (11)
C9	0.0551 (14)	0.0364 (10)	0.0640 (13)	−0.0004 (11)	−0.0007 (11)	−0.0090 (10)
C10	0.0525 (14)	0.0422 (11)	0.0508 (11)	−0.0012 (11)	0.0024 (10)	−0.0061 (10)
C11	0.0620 (16)	0.0448 (12)	0.0704 (14)	−0.0027 (12)	0.0007 (12)	−0.0039 (11)
C12	0.0711 (19)	0.0627 (16)	0.0817 (18)	−0.0081 (15)	0.0004 (15)	−0.0113 (14)
C13	0.0618 (17)	0.089 (2)	0.0700 (16)	−0.0041 (18)	−0.0101 (14)	−0.0109 (15)
C14	0.0758 (19)	0.0778 (18)	0.0666 (15)	0.0019 (17)	−0.0127 (14)	0.0110 (14)
C15	0.0706 (17)	0.0517 (13)	0.0630 (13)	−0.0048 (13)	−0.0055 (13)	0.0068 (12)
Cl1	0.1070 (7)	0.0629 (4)	0.1016 (5)	−0.0142 (5)	0.0117 (5)	−0.0220 (4)
N1	0.0576 (12)	0.0362 (8)	0.0632 (11)	0.0002 (9)	−0.0047 (9)	0.0007 (8)
O1	0.0723 (12)	0.0446 (9)	0.0830 (12)	0.0140 (9)	−0.0153 (10)	−0.0070 (9)
O2	0.0799 (13)	0.0359 (8)	0.1039 (14)	−0.0044 (9)	−0.0200 (11)	0.0020 (9)

C1—C2	1.381 (4)	C8—H8	0.9800
C1—C6	1.391 (3)	C9—O2	1.221 (3)
C1—Cl1	1.734 (3)	C9—N1	1.337 (3)
C2—C3	1.378 (5)	C10—C11	1.377 (3)
C2—H2	0.9300	C10—C15	1.387 (4)
C3—C4	1.364 (5)	C10—N1	1.420 (3)
C3—H3	0.9300	C11—C12	1.397 (4)
C4—C5	1.391 (5)	C11—H11	0.9300
C4—H4	0.9300	C12—C13	1.374 (4)
C5—C6	1.383 (4)	C12—H12	0.9300
C5—H5	0.9300	C13—C14	1.364 (4)
C6—C7	1.483 (4)	C13—H13	0.9300
C7—O1	1.432 (3)	C14—C15	1.395 (4)
C7—C8	1.472 (4)	C14—H14	0.9300
C7—H7	0.9800	C15—H15	0.9300
C8—O1	1.429 (3)	N1—H1	0.8600
C8—C9	1.504 (4)
C2—C1—C6	121.0 (3)	C7—C8—H8	115.6
C2—C1—Cl1	119.9 (2)	C9—C8—H8	115.6
C6—C1—Cl1	119.1 (2)	O2—C9—N1	126.0 (2)
C3—C2—C1	119.6 (3)	O2—C9—C8	117.9 (2)
C3—C2—H2	120.2	N1—C9—C8	116.1 (2)
C1—C2—H2	120.2	C11—C10—C15	120.0 (2)
C4—C3—C2	120.7 (3)	C11—C10—N1	116.7 (2)
C4—C3—H3	119.7	C15—C10—N1	123.3 (2)
C2—C3—H3	119.7	C10—C11—C12	120.5 (3)
C3—C4—C5	119.5 (3)	C10—C11—H11	119.8
C3—C4—H4	120.3	C12—C11—H11	119.8
C5—C4—H4	120.3	C13—C12—C11	119.7 (3)
C6—C5—C4	121.2 (3)	C13—C12—H12	120.1
C6—C5—H5	119.4	C11—C12—H12	120.1
C4—C5—H5	119.4	C14—C13—C12	119.6 (3)
C5—C6—C1	118.0 (3)	C14—C13—H13	120.2
C5—C6—C7	121.7 (2)	C12—C13—H13	120.2
C1—C6—C7	120.2 (2)	C13—C14—C15	121.9 (3)
O1—C7—C8	58.96 (16)	C13—C14—H14	119.1
O1—C7—C6	117.0 (2)	C15—C14—H14	119.1
C8—C7—C6	124.5 (2)	C10—C15—C14	118.4 (3)
O1—C7—H7	114.8	C10—C15—H15	120.8
C8—C7—H7	114.8	C14—C15—H15	120.8
C6—C7—H7	114.8	C9—N1—C10	127.89 (19)
O1—C8—C7	59.12 (16)	C9—N1—H1	116.1
O1—C8—C9	119.1 (2)	C10—N1—H1	116.1
C7—C8—C9	120.1 (2)	C8—O1—C7	61.92 (15)
O1—C8—H8	115.6

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	2.38	2.801 (3)	111
N1—H1···O2i	0.86	2.16	2.973 (2)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86	2.38	2.801 (3)	111
N1—H1⋯O2i	0.86	2.16	2.973 (2)	158

Symmetry code: (i) .