3-(4-Nitro-phen-yl)-N-phenyl-oxirane-2-carboxamide.

The mol-ecule of the title compound, C(15)H(12)N(2)O(4), adopts a syn conformation with the terminal benzene rings located on the same sides of the central epoxide ring. The epoxide ring makes dihedral angles of 71.08 (18) and 60.83 (17)° with the two benzene rings. Weak inter-molecular C-H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For epoxide-containing compounds used as building blocks in synthesis, see: Righi et al. (1996 ▶); Bhatia et al. (1999 ▶); Meth-Cohn et al. (1999 ▶); Thijs et al. (1990 ▶).

Experimental

Crystal data

C15H12N2O4

M = 284.27

Monoclinic,

a = 5.9800 (3) Å

b = 5.1960 (4) Å

c = 21.503 (5) Å

β = 96.105 (5)°

V = 664.35 (17) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.36 × 0.30 × 0.10 mm

Data collection

Oxford Diffraction Gemini S Ultra diffractometer

Absorption correction: none

6118 measured reflections

1515 independent reflections

821 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.042

S = 1.13

1515 reflections

194 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.12 e Å−3

Δρmin = −0.13 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; 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 (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809029699/xu2566sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809029699/xu2566Isup2.hkl

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

C15H12N2O4	F(000) = 296
Mr = 284.27	Dx = 1.421 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1633 reflections
a = 5.9800 (3) Å	θ = 2.9–29.0°
b = 5.1960 (4) Å	µ = 0.11 mm−1
c = 21.503 (5) Å	T = 293 K
β = 96.105 (5)°	Block, colorless
V = 664.35 (17) Å3	0.36 × 0.30 × 0.10 mm
Z = 2

Oxford Diffraction Gemini S Ultra diffractometer	821 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.054
graphite	θmax = 26.4°, θmin = 2.9°
ω scans	h = −7→7
6118 measured reflections	k = −6→5
1515 independent reflections	l = −26→26

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.042	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ2(Fo2) + (0.0006P)2] where P = (Fo2 + 2Fc2)/3
1515 reflections	(Δ/σ)max < 0.001
194 parameters	Δρmax = 0.12 e Å−3
2 restraints	Δρmin = −0.13 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
O4	0.6579 (3)	0.2311 (5)	0.48448 (11)	0.0686 (8)
O2	0.7928 (4)	1.2561 (5)	0.25607 (9)	0.0691 (7)
N1	0.8102 (5)	0.8270 (6)	0.17913 (12)	0.0573 (8)
O3	0.3472 (3)	0.2679 (5)	0.42342 (10)	0.0766 (8)
N2	0.5421 (5)	0.3314 (6)	0.44030 (13)	0.0566 (9)
C10	0.8251 (5)	0.9283 (6)	0.34170 (14)	0.0437 (9)
C14	0.8515 (4)	0.6302 (6)	0.42748 (13)	0.0459 (9)
H14	0.9301	0.5606	0.4632	0.055*
C4	0.7716 (6)	0.6203 (7)	0.13644 (14)	0.0511 (10)
C15	0.9424 (4)	0.8237 (7)	0.39512 (14)	0.0491 (9)
H15	1.0848	0.8861	0.4090	0.059*
O1	1.1883 (4)	0.7951 (6)	0.20507 (10)	0.0919 (9)
C13	0.6412 (5)	0.5415 (7)	0.40592 (15)	0.0398 (9)
C11	0.6126 (5)	0.8330 (7)	0.32131 (13)	0.0524 (10)
H11	0.5323	0.9008	0.2856	0.063*
C8	1.0022 (6)	1.1420 (7)	0.24713 (14)	0.0596 (10)
H8	1.1214	1.2660	0.2410	0.071*
C12	0.5216 (5)	0.6395 (7)	0.35375 (14)	0.0530 (10)
H12	0.3794	0.5755	0.3403	0.064*
C9	0.9241 (5)	1.1506 (7)	0.30983 (14)	0.0527 (10)
H9	0.9999	1.2786	0.3382	0.063*
C5	0.9264 (5)	0.5501 (8)	0.09757 (14)	0.0604 (11)
H5	1.0639	0.6348	0.0996	0.072*
C7	1.0093 (7)	0.9023 (7)	0.20860 (15)	0.0618 (11)
C6	0.8787 (6)	0.3529 (8)	0.05514 (15)	0.0726 (12)
H6	0.9847	0.3064	0.0285	0.087*
C3	0.5675 (5)	0.4925 (8)	0.13414 (15)	0.0646 (11)
H3	0.4623	0.5382	0.1611	0.078*
C1	0.6773 (6)	0.2246 (7)	0.05169 (15)	0.0703 (12)
H1	0.6462	0.0918	0.0231	0.084*
C2	0.5224 (5)	0.2959 (9)	0.09128 (17)	0.0710 (11)
H2	0.3850	0.2107	0.0892	0.085*
H4	0.678 (3)	0.890 (6)	0.1938 (12)	0.087 (13)*

	U11	U22	U33	U12	U13	U23
O4	0.0732 (16)	0.057 (2)	0.0750 (16)	−0.0043 (14)	0.0071 (12)	0.0141 (15)
O2	0.1047 (18)	0.0473 (19)	0.0558 (15)	0.0221 (16)	0.0106 (14)	−0.0014 (16)
N1	0.066 (2)	0.061 (3)	0.0451 (18)	0.019 (2)	0.0055 (17)	−0.004 (2)
O3	0.0612 (15)	0.070 (2)	0.0974 (17)	−0.0300 (15)	0.0046 (12)	−0.0074 (17)
N2	0.062 (2)	0.048 (3)	0.061 (2)	−0.0070 (19)	0.0153 (17)	−0.012 (2)
C10	0.054 (2)	0.040 (3)	0.038 (2)	−0.0007 (18)	0.0097 (17)	−0.0077 (19)
C14	0.047 (2)	0.045 (3)	0.044 (2)	−0.0014 (19)	−0.0018 (16)	−0.003 (2)
C4	0.070 (2)	0.047 (3)	0.036 (2)	0.022 (2)	0.0045 (19)	0.000 (2)
C15	0.0508 (19)	0.055 (3)	0.0412 (19)	−0.003 (2)	0.0016 (17)	−0.005 (2)
O1	0.0763 (16)	0.104 (2)	0.0930 (19)	0.0260 (17)	−0.0025 (14)	−0.047 (2)
C13	0.047 (2)	0.034 (3)	0.040 (2)	−0.0027 (17)	0.0094 (17)	−0.0042 (17)
C11	0.054 (2)	0.056 (3)	0.046 (2)	0.012 (2)	−0.0023 (17)	−0.001 (2)
C8	0.091 (3)	0.039 (3)	0.050 (2)	−0.005 (2)	0.0143 (19)	0.000 (2)
C12	0.046 (2)	0.061 (3)	0.051 (2)	−0.005 (2)	0.0018 (18)	−0.009 (2)
C9	0.074 (2)	0.040 (3)	0.044 (2)	0.003 (2)	0.0054 (19)	−0.007 (2)
C5	0.074 (2)	0.065 (3)	0.044 (2)	0.004 (2)	0.014 (2)	−0.009 (2)
C7	0.084 (3)	0.056 (3)	0.046 (2)	0.007 (2)	0.012 (2)	0.004 (2)
C6	0.085 (3)	0.075 (4)	0.058 (2)	0.004 (3)	0.009 (2)	−0.012 (3)
C3	0.061 (2)	0.069 (3)	0.064 (3)	0.015 (2)	0.008 (2)	0.008 (2)
C1	0.093 (3)	0.052 (3)	0.062 (3)	0.012 (3)	−0.008 (2)	−0.004 (2)
C2	0.068 (3)	0.065 (3)	0.077 (3)	−0.006 (2)	−0.008 (2)	0.004 (3)

O4—N2	1.230 (3)	C13—C12	1.364 (3)
O2—C8	1.417 (3)	C11—C12	1.369 (4)
O2—C9	1.435 (3)	C11—H11	0.9300
N1—C7	1.346 (4)	C8—C9	1.474 (4)
N1—C4	1.416 (4)	C8—C7	1.499 (4)
N1—H4	0.940 (10)	C8—H8	0.9800
O3—N2	1.229 (2)	C12—H12	0.9300
N2—C13	1.477 (4)	C9—H9	0.9800
C10—C11	1.391 (3)	C5—C6	1.381 (4)
C10—C15	1.391 (4)	C5—H5	0.9300
C10—C9	1.497 (4)	C6—C1	1.371 (4)
C14—C15	1.368 (4)	C6—H6	0.9300
C14—C13	1.373 (3)	C3—C2	1.383 (5)
C14—H14	0.9300	C3—H3	0.9300
C4—C5	1.361 (4)	C1—C2	1.374 (4)
C4—C3	1.386 (4)	C1—H1	0.9300
C15—H15	0.9300	C2—H2	0.9300
O1—C7	1.216 (3)
C8—O2—C9	62.22 (18)	C9—C8—H8	114.1
C7—N1—C4	126.9 (3)	C7—C8—H8	114.1
C7—N1—H4	118.2 (19)	C13—C12—C11	119.4 (3)
C4—N1—H4	113.5 (19)	C13—C12—H12	120.3
O3—N2—O4	123.5 (3)	C11—C12—H12	120.3
O3—N2—C13	118.0 (3)	O2—C9—C8	58.28 (18)
O4—N2—C13	118.5 (3)	O2—C9—C10	117.0 (3)
C11—C10—C15	119.0 (3)	C8—C9—C10	125.1 (3)
C11—C10—C9	121.5 (3)	O2—C9—H9	114.7
C15—C10—C9	119.4 (3)	C8—C9—H9	114.7
C15—C14—C13	118.3 (3)	C10—C9—H9	114.7
C15—C14—H14	120.8	C4—C5—C6	119.9 (3)
C13—C14—H14	120.8	C4—C5—H5	120.1
C5—C4—C3	120.2 (3)	C6—C5—H5	120.1
C5—C4—N1	121.8 (4)	O1—C7—N1	125.3 (4)
C3—C4—N1	118.0 (3)	O1—C7—C8	119.5 (4)
C14—C15—C10	120.9 (3)	N1—C7—C8	115.2 (3)
C14—C15—H15	119.5	C1—C6—C5	121.0 (3)
C10—C15—H15	119.5	C1—C6—H6	119.5
C12—C13—C14	122.3 (3)	C5—C6—H6	119.5
C12—C13—N2	119.0 (3)	C2—C3—C4	119.1 (3)
C14—C13—N2	118.7 (3)	C2—C3—H3	120.4
C12—C11—C10	120.0 (3)	C4—C3—H3	120.4
C12—C11—H11	120.0	C6—C1—C2	118.8 (4)
C10—C11—H11	120.0	C6—C1—H1	120.6
O2—C8—C9	59.50 (19)	C2—C1—H1	120.6
O2—C8—C7	120.0 (3)	C1—C2—C3	121.0 (4)
C9—C8—C7	124.1 (3)	C1—C2—H2	119.5
O2—C8—H8	114.1	C3—C2—H2	119.5
C7—N1—C4—C5	−32.3 (5)	C7—C8—C9—C10	−4.9 (6)
C7—N1—C4—C3	149.1 (3)	C11—C10—C9—O2	−1.9 (4)
C13—C14—C15—C10	0.0 (4)	C15—C10—C9—O2	−178.1 (3)
C11—C10—C15—C14	−0.1 (4)	C11—C10—C9—C8	−70.6 (4)
C9—C10—C15—C14	176.2 (3)	C15—C10—C9—C8	113.2 (4)
C15—C14—C13—C12	0.0 (4)	C3—C4—C5—C6	0.8 (5)
C15—C14—C13—N2	179.6 (3)	N1—C4—C5—C6	−177.8 (3)
O3—N2—C13—C12	−6.0 (4)	C4—N1—C7—O1	−3.5 (5)
O4—N2—C13—C12	174.6 (3)	C4—N1—C7—C8	175.0 (3)
O3—N2—C13—C14	174.4 (3)	O2—C8—C7—O1	−174.5 (3)
O4—N2—C13—C14	−5.1 (4)	C9—C8—C7—O1	−103.0 (4)
C15—C10—C11—C12	0.1 (4)	O2—C8—C7—N1	6.9 (4)
C9—C10—C11—C12	−176.1 (3)	C9—C8—C7—N1	78.4 (4)
C9—O2—C8—C7	114.3 (4)	C4—C5—C6—C1	−0.4 (5)
C14—C13—C12—C11	0.1 (4)	C5—C4—C3—C2	−1.0 (5)
N2—C13—C12—C11	−179.6 (3)	N1—C4—C3—C2	177.7 (3)
C10—C11—C12—C13	−0.1 (4)	C5—C6—C1—C2	0.1 (5)
C8—O2—C9—C10	−116.3 (3)	C6—C1—C2—C3	−0.3 (5)
C7—C8—C9—O2	−107.6 (4)	C4—C3—C2—C1	0.7 (5)
O2—C8—C9—C10	102.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1i	0.93	2.39	3.267 (4)	158
C15—H15···O3ii	0.93	2.53	3.353 (4)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1i	0.93	2.39	3.267 (4)	158
C15—H15⋯O3ii	0.93	2.53	3.353 (4)	148

Symmetry codes: (i) ; (ii) .