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

In the mol-ecule of the title compound, C(15)H(12)BrNO(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 59.90 (13) and 68.01 (12)°. Inter-molecular N-H⋯O and C-H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For epoxide-containing compounds used as building blocks in synthesis, see: Flisak et al. (1993 ▶); Watanabe et al. (1998 ▶); Zhu & Espenson (1995 ▶). For related structures, see: He (2009 ▶); He & Chen (2009 ▶).

Experimental

Crystal data

C15H12BrNO2

M = 318.17

Orthorhombic,

a = 6.71700 (10) Å

b = 10.0370 (2) Å

c = 20.4287 (3) Å

V = 1377.27 (4) Å3

Z = 4

Cu Kα radiation

μ = 4.05 mm−1

T = 295 K

0.40 × 0.40 × 0.36 mm

Data collection

Oxford Diffraction Gemini S Ultra diffractometer

Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2009 ▶) T min = 0.294, T max = 0.324

17721 measured reflections

2701 independent reflections

2675 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.069

S = 1.01

2701 reflections

177 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.42 e Å−3

Absolute structure: Flack (1983 ▶), 1104 Friedel pairs

Flack parameter: −0.008 (18)

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/S1600536809045929/xu2664sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045929/xu2664Isup2.hkl

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

C15H12BrNO2	F(000) = 640
Mr = 318.17	Dx = 1.534 Mg m−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2ac 2ab	Cell parameters from 15647 reflections
a = 6.7170 (1) Å	θ = 2.2–72.1°
b = 10.0370 (2) Å	µ = 4.05 mm−1
c = 20.4287 (3) Å	T = 295 K
V = 1377.27 (4) Å3	Block, colorless
Z = 4	0.40 × 0.40 × 0.36 mm

Oxford Diffraction Gemini S Ultra diffractometer	2701 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	2675 reflections with I > 2σ(I)
mirror	Rint = 0.028
Detector resolution: 15.9149 pixels mm-1	θmax = 72.3°, θmin = 4.3°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −11→12
Tmin = 0.294, Tmax = 0.324	l = −24→25
17721 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.028	w = 1/[σ2(Fo2) + (0.035P)2 + 0.5235P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.069	(Δ/σ)max = 0.001
S = 1.00	Δρmax = 0.33 e Å−3
2701 reflections	Δρmin = −0.42 e Å−3
177 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0074 (5)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1104 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: −0.008 (18)

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
Br1	−0.14003 (5)	0.63054 (3)	0.557209 (16)	0.07563 (15)
O1	−0.1933 (3)	0.23595 (16)	0.66346 (9)	0.0567 (4)
O2	−0.0059 (3)	0.50889 (16)	0.76057 (10)	0.0637 (5)
N1	0.1077 (3)	0.29560 (18)	0.75313 (9)	0.0437 (4)
C5	0.1656 (4)	0.2794 (3)	0.59008 (13)	0.0582 (6)
H5	0.1480	0.2015	0.6140	0.070*
C6	0.0186 (3)	0.3772 (2)	0.59138 (10)	0.0470 (5)
C15	0.3410 (4)	0.4080 (2)	0.82806 (11)	0.0520 (5)
H15	0.2588	0.4823	0.8314	0.062*
C9	−0.0201 (3)	0.3947 (2)	0.74074 (11)	0.0440 (4)
C8	−0.1951 (3)	0.3600 (2)	0.69813 (11)	0.0467 (5)
H8	−0.3253	0.3893	0.7143	0.056*
C10	0.2882 (3)	0.3016 (2)	0.78857 (10)	0.0407 (4)
C7	−0.1724 (3)	0.3564 (2)	0.62606 (11)	0.0499 (5)
H7	−0.2912	0.3828	0.6014	0.060*
C11	0.4155 (3)	0.1931 (2)	0.78350 (11)	0.0494 (5)
H11	0.3828	0.1227	0.7559	0.059*
C1	0.0535 (4)	0.4931 (2)	0.55591 (11)	0.0502 (5)
C12	0.5905 (4)	0.1889 (3)	0.81914 (14)	0.0607 (6)
H12	0.6734	0.1149	0.8162	0.073*
C2	0.2261 (5)	0.5119 (3)	0.52052 (13)	0.0654 (7)
H2	0.2477	0.5908	0.4977	0.078*
C3	0.3657 (5)	0.4116 (3)	0.51958 (14)	0.0723 (7)
H3	0.4815	0.4227	0.4952	0.087*
C13	0.6420 (4)	0.2934 (3)	0.85879 (13)	0.0655 (7)
H13	0.7594	0.2905	0.8829	0.079*
C14	0.5199 (4)	0.4020 (3)	0.86281 (13)	0.0641 (7)
H14	0.5567	0.4734	0.8892	0.077*
C4	0.3375 (4)	0.2965 (3)	0.55369 (14)	0.0680 (7)
H4	0.4334	0.2297	0.5525	0.082*
H1	0.074 (3)	0.225 (3)	0.7406 (12)	0.037 (6)*

	U11	U22	U33	U12	U13	U23
Br1	0.0896 (2)	0.05464 (17)	0.0827 (2)	0.01486 (15)	0.01432 (17)	0.01807 (14)
O1	0.0611 (10)	0.0400 (8)	0.0689 (10)	−0.0133 (7)	−0.0136 (8)	0.0087 (7)
O2	0.0677 (10)	0.0342 (8)	0.0891 (12)	0.0036 (8)	−0.0200 (10)	−0.0011 (8)
N1	0.0487 (10)	0.0311 (8)	0.0515 (9)	−0.0032 (8)	−0.0056 (8)	−0.0002 (7)
C5	0.0618 (15)	0.0547 (13)	0.0581 (13)	0.0042 (12)	−0.0126 (12)	−0.0037 (11)
C6	0.0500 (11)	0.0458 (11)	0.0453 (10)	−0.0031 (11)	−0.0122 (8)	−0.0024 (9)
C15	0.0584 (13)	0.0455 (11)	0.0520 (11)	0.0046 (10)	−0.0047 (11)	−0.0052 (9)
C9	0.0473 (10)	0.0332 (10)	0.0515 (11)	−0.0039 (8)	−0.0011 (9)	0.0071 (8)
C8	0.0418 (10)	0.0375 (10)	0.0609 (12)	−0.0063 (9)	−0.0036 (8)	0.0089 (10)
C10	0.0442 (10)	0.0386 (10)	0.0392 (9)	−0.0030 (8)	0.0020 (8)	0.0079 (8)
C7	0.0459 (11)	0.0448 (11)	0.0589 (12)	−0.0055 (10)	−0.0150 (9)	0.0106 (10)
C11	0.0517 (12)	0.0425 (11)	0.0541 (12)	0.0011 (9)	0.0042 (9)	0.0029 (9)
C1	0.0604 (12)	0.0462 (11)	0.0441 (10)	−0.0012 (9)	−0.0009 (10)	−0.0020 (10)
C12	0.0477 (12)	0.0615 (14)	0.0730 (16)	0.0100 (11)	0.0029 (11)	0.0138 (12)
C2	0.0782 (17)	0.0652 (16)	0.0528 (13)	−0.0086 (14)	0.0095 (12)	−0.0001 (12)
C3	0.0631 (16)	0.091 (2)	0.0629 (15)	−0.0026 (16)	0.0099 (14)	−0.0143 (14)
C13	0.0525 (13)	0.0838 (19)	0.0602 (13)	0.0019 (15)	−0.0100 (12)	0.0111 (13)
C14	0.0696 (16)	0.0679 (16)	0.0548 (13)	−0.0056 (14)	−0.0149 (12)	−0.0083 (12)
C4	0.0624 (15)	0.0748 (17)	0.0669 (15)	0.0141 (13)	−0.0095 (15)	−0.0156 (14)

Br1—C1	1.896 (2)	C8—H8	0.9800
O1—C8	1.433 (3)	C10—C11	1.388 (3)
O1—C7	1.437 (3)	C7—H7	0.9800
O2—C9	1.219 (3)	C11—C12	1.384 (4)
N1—C9	1.338 (3)	C11—H11	0.9300
N1—C10	1.414 (3)	C1—C2	1.380 (4)
N1—H1	0.78 (3)	C12—C13	1.370 (4)
C5—C4	1.384 (4)	C12—H12	0.9300
C5—C6	1.392 (3)	C2—C3	1.375 (5)
C5—H5	0.9300	C2—H2	0.9300
C6—C1	1.390 (3)	C3—C4	1.363 (5)
C6—C7	1.481 (3)	C3—H3	0.9300
C15—C10	1.385 (3)	C13—C14	1.366 (4)
C15—C14	1.397 (4)	C13—H13	0.9300
C15—H15	0.9300	C14—H14	0.9300
C9—C8	1.503 (3)	C4—H4	0.9300
C8—C7	1.481 (3)
C8—O1—C7	62.11 (14)	O1—C7—H7	114.9
C9—N1—C10	127.97 (19)	C6—C7—H7	114.9
C9—N1—H1	115.1 (18)	C8—C7—H7	114.9
C10—N1—H1	116.8 (18)	C12—C11—C10	120.6 (2)
C4—C5—C6	121.0 (3)	C12—C11—H11	119.7
C4—C5—H5	119.5	C10—C11—H11	119.7
C6—C5—H5	119.5	C2—C1—C6	121.9 (2)
C1—C6—C5	117.4 (2)	C2—C1—Br1	118.96 (19)
C1—C6—C7	120.9 (2)	C6—C1—Br1	119.09 (17)
C5—C6—C7	121.7 (2)	C13—C12—C11	120.1 (2)
C10—C15—C14	118.9 (2)	C13—C12—H12	119.9
C10—C15—H15	120.6	C11—C12—H12	119.9
C14—C15—H15	120.6	C3—C2—C1	118.7 (3)
O2—C9—N1	125.9 (2)	C3—C2—H2	120.6
O2—C9—C8	118.1 (2)	C1—C2—H2	120.6
N1—C9—C8	116.05 (19)	C4—C3—C2	121.2 (3)
O1—C8—C7	59.09 (14)	C4—C3—H3	119.4
O1—C8—C9	118.74 (18)	C2—C3—H3	119.4
C7—C8—C9	120.07 (19)	C14—C13—C12	119.7 (2)
O1—C8—H8	115.7	C14—C13—H13	120.2
C7—C8—H8	115.7	C12—C13—H13	120.2
C9—C8—H8	115.7	C13—C14—C15	121.3 (2)
C15—C10—C11	119.4 (2)	C13—C14—H14	119.3
C15—C10—N1	123.5 (2)	C15—C14—H14	119.3
C11—C10—N1	117.1 (2)	C3—C4—C5	119.7 (3)
O1—C7—C6	117.2 (2)	C3—C4—H4	120.1
O1—C7—C8	58.80 (14)	C5—C4—H4	120.1
C6—C7—C8	124.15 (18)
C4—C5—C6—C1	−1.3 (3)	C9—C8—C7—O1	107.5 (2)
C4—C5—C6—C7	175.4 (2)	O1—C8—C7—C6	−103.6 (2)
C10—N1—C9—O2	−3.1 (4)	C9—C8—C7—C6	3.9 (4)
C10—N1—C9—C8	176.5 (2)	C15—C10—C11—C12	2.1 (3)
C7—O1—C8—C9	−109.7 (2)	N1—C10—C11—C12	−176.9 (2)
O2—C9—C8—O1	167.2 (2)	C5—C6—C1—C2	0.1 (3)
N1—C9—C8—O1	−12.5 (3)	C7—C6—C1—C2	−176.7 (2)
O2—C9—C8—C7	98.3 (3)	C5—C6—C1—Br1	−178.98 (16)
N1—C9—C8—C7	−81.4 (3)	C7—C6—C1—Br1	4.2 (3)
C14—C15—C10—C11	−1.2 (3)	C10—C11—C12—C13	−1.4 (4)
C14—C15—C10—N1	177.8 (2)	C6—C1—C2—C3	1.1 (4)
C9—N1—C10—C15	14.1 (3)	Br1—C1—C2—C3	−179.8 (2)
C9—N1—C10—C11	−166.9 (2)	C1—C2—C3—C4	−1.2 (4)
C8—O1—C7—C6	115.3 (2)	C11—C12—C13—C14	−0.2 (4)
C1—C6—C7—O1	−177.83 (19)	C12—C13—C14—C15	1.1 (4)
C5—C6—C7—O1	5.5 (3)	C10—C15—C14—C13	−0.4 (4)
C1—C6—C7—C8	−108.6 (2)	C2—C3—C4—C5	0.0 (4)
C5—C6—C7—C8	74.7 (3)	C6—C5—C4—C3	1.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.79 (3)	2.22 (3)	2.971 (2)	161 (2)
C15—H15···O1ii	0.93	2.59	3.442 (3)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.79 (3)	2.22 (3)	2.971 (2)	161 (2)
C15—H15⋯O1ii	0.93	2.59	3.442 (3)	153

Symmetry codes: (i) ; (ii) .