N,N'-Diphenyl-but-2-enediamide.

In the title compound, C(16)H(14)N(2)O(2), the conformations of the N-H and C=O bonds in the C-NH-CO-CH =CH-CO-NH-C segment are anti to each other. The two C=O bonds are also anti to each other. The two phenyl rings make an inter-planar angle of 41.2 (1)°. An intra-molecular N-H⋯O hydrogen bond occurs. In the crystal, inter-molecular N-H⋯O hydrogen bonding links the mol-ecules into infinite chains along the a axis.

Related literature

For related structures, see: Gowda, Foro et al. (2010 ▶); Gowda, Tokarčík et al. (2010 ▶).

Experimental

Crystal data

C16H14N2O2

M = 266.29

Orthorhombic,

a = 6.604 (1) Å

b = 13.358 (2) Å

c = 15.474 (2) Å

V = 1365.1 (3) Å3

Z = 4

Cu Kα radiation

μ = 0.70 mm−1

T = 299 K

0.35 × 0.30 × 0.25 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

3656 measured reflections

1422 independent reflections

1339 reflections with I > 2σ(I)

R int = 0.117

3 standard reflections every 120 min intensity decay: 0.5%

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.100

S = 1.06

1422 reflections

188 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.11 e Å−3

Δρmin = −0.13 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810051330/ng5082sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051330/ng5082Isup2.hkl

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

C16H14N2O2	F(000) = 560
Mr = 266.29	Dx = 1.296 Mg m−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 6.604 (1) Å	θ = 8.0–20.1°
b = 13.358 (2) Å	µ = 0.70 mm−1
c = 15.474 (2) Å	T = 299 K
V = 1365.1 (3) Å3	Prism, orange
Z = 4	0.35 × 0.30 × 0.25 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.117
Radiation source: fine-focus sealed tube	θmax = 66.9°, θmin = 4.4°
graphite	h = 0→7
ω scans	k = −15→15
3656 measured reflections	l = −18→5
1422 independent reflections	3 standard reflections every 120 min
1339 reflections with I > 2σ(I)	intensity decay: 0.5%

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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.0279P)2 + 0.0657P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.025
1422 reflections	Δρmax = 0.11 e Å−3
188 parameters	Δρmin = −0.13 e Å−3
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0140 (9)

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	−0.0250 (3)	0.71987 (19)	0.85351 (17)	0.0547 (6)
C2	−0.0384 (3)	0.8224 (2)	0.8469 (2)	0.0678 (7)
H2	0.0653	0.8579	0.8202	0.081*
C3	−0.2036 (4)	0.8730 (2)	0.8794 (2)	0.0761 (8)
H3	−0.2105	0.9424	0.8747	0.091*
C4	−0.3580 (4)	0.8212 (3)	0.9186 (2)	0.0760 (8)
H4	−0.4702	0.8550	0.9402	0.091*
C5	−0.3449 (3)	0.7192 (3)	0.9256 (2)	0.0750 (9)
H5	−0.4490	0.6841	0.9525	0.090*
C6	−0.1793 (3)	0.6671 (2)	0.89343 (17)	0.0630 (7)
H6	−0.1722	0.5978	0.8986	0.076*
C7	0.2087 (3)	0.57754 (19)	0.82283 (19)	0.0610 (7)
C8	0.4088 (3)	0.5604 (2)	0.78135 (18)	0.0653 (7)
H8	0.4646	0.6163	0.7545	0.078*
C9	0.5210 (3)	0.4774 (2)	0.7765 (2)	0.0683 (8)
H9	0.6417	0.4879	0.7469	0.082*
C10	0.4997 (3)	0.3727 (2)	0.80698 (18)	0.0597 (6)
C11	0.2874 (3)	0.2512 (2)	0.88312 (16)	0.0581 (6)
C12	0.4328 (4)	0.1895 (2)	0.92070 (19)	0.0731 (8)
H12	0.5675	0.2098	0.9228	0.088*
C13	0.3764 (4)	0.0982 (3)	0.9549 (2)	0.0839 (9)
H13	0.4740	0.0570	0.9796	0.101*
C14	0.1789 (4)	0.0676 (3)	0.9529 (2)	0.0882 (9)
H14	0.1423	0.0059	0.9758	0.106*
C15	0.0352 (4)	0.1288 (2)	0.9168 (2)	0.0856 (9)
H15	−0.0994	0.1083	0.9158	0.103*
C16	0.0868 (3)	0.2196 (2)	0.8821 (2)	0.0687 (7)
H16	−0.0124	0.2603	0.8578	0.082*
N1	0.1514 (2)	0.67393 (16)	0.81901 (16)	0.0596 (6)
H1N	0.227 (3)	0.7171 (19)	0.7929 (15)	0.071*
N2	0.3325 (2)	0.34685 (16)	0.85126 (16)	0.0617 (6)
H2N	0.241 (3)	0.3975 (19)	0.8579 (19)	0.074*
O1	0.1061 (2)	0.51235 (14)	0.85749 (17)	0.0956 (8)
O2	0.6377 (2)	0.31390 (16)	0.79069 (14)	0.0769 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0536 (9)	0.0455 (12)	0.0648 (13)	0.0038 (9)	0.0018 (10)	0.0006 (15)
C2	0.0679 (10)	0.0500 (13)	0.0856 (18)	0.0021 (11)	0.0090 (13)	0.0060 (19)
C3	0.0837 (14)	0.0501 (14)	0.0944 (18)	0.0131 (12)	−0.0005 (16)	0.003 (2)
C4	0.0719 (12)	0.0706 (18)	0.0856 (19)	0.0169 (14)	0.0090 (14)	0.003 (2)
C5	0.0609 (11)	0.0733 (19)	0.091 (2)	0.0053 (11)	0.0134 (13)	0.009 (2)
C6	0.0547 (9)	0.0530 (14)	0.0812 (16)	0.0001 (10)	0.0045 (11)	0.0110 (18)
C7	0.0570 (9)	0.0424 (12)	0.0836 (17)	0.0014 (9)	0.0108 (12)	0.0025 (17)
C8	0.0576 (10)	0.0479 (12)	0.0903 (17)	−0.0045 (10)	0.0169 (12)	0.0066 (18)
C9	0.0561 (9)	0.0573 (15)	0.091 (2)	0.0007 (10)	0.0161 (13)	0.0009 (19)
C10	0.0553 (10)	0.0499 (13)	0.0740 (15)	0.0027 (9)	0.0055 (11)	−0.0068 (17)
C11	0.0680 (10)	0.0448 (12)	0.0616 (13)	0.0093 (10)	0.0031 (11)	−0.0048 (16)
C12	0.0715 (12)	0.0619 (15)	0.0860 (18)	0.0168 (13)	−0.0039 (13)	0.004 (2)
C13	0.0977 (17)	0.0612 (17)	0.093 (2)	0.0209 (16)	−0.0119 (17)	0.009 (2)
C14	0.1098 (18)	0.0530 (15)	0.102 (2)	−0.0005 (16)	0.0011 (18)	0.017 (2)
C15	0.0820 (14)	0.0579 (16)	0.117 (3)	−0.0023 (13)	−0.0005 (16)	0.003 (2)
C16	0.0657 (12)	0.0547 (14)	0.0856 (18)	0.0070 (11)	−0.0023 (13)	0.0048 (19)
N1	0.0511 (8)	0.0435 (10)	0.0841 (14)	−0.0005 (8)	0.0082 (9)	0.0044 (14)
N2	0.0568 (8)	0.0468 (11)	0.0816 (14)	0.0093 (8)	0.0079 (10)	0.0028 (14)
O1	0.0772 (9)	0.0461 (9)	0.164 (2)	0.0100 (8)	0.0493 (12)	0.0271 (16)
O2	0.0675 (8)	0.0636 (12)	0.0995 (13)	0.0182 (9)	0.0157 (9)	−0.0071 (14)

C1—C2	1.376 (4)	C9—H9	0.9300
C1—C6	1.385 (3)	C10—O2	1.230 (3)
C1—N1	1.421 (3)	C10—N2	1.345 (3)
C2—C3	1.379 (4)	C11—C16	1.390 (3)
C2—H2	0.9300	C11—C12	1.392 (3)
C3—C4	1.374 (4)	C11—N2	1.402 (3)
C3—H3	0.9300	C12—C13	1.381 (5)
C4—C5	1.370 (5)	C12—H12	0.9300
C4—H4	0.9300	C13—C14	1.367 (4)
C5—C6	1.388 (3)	C13—H13	0.9300
C5—H5	0.9300	C14—C15	1.372 (4)
C6—H6	0.9300	C14—H14	0.9300
C7—O1	1.227 (3)	C15—C16	1.370 (4)
C7—N1	1.344 (3)	C15—H15	0.9300
C7—C8	1.487 (3)	C16—H16	0.9300
C8—C9	1.335 (4)	N1—H1N	0.862 (18)
C8—H8	0.9300	N2—H2N	0.912 (18)
C9—C10	1.482 (4)
C2—C1—C6	119.5 (2)	O2—C10—N2	123.3 (3)
C2—C1—N1	117.0 (2)	O2—C10—C9	117.9 (2)
C6—C1—N1	123.4 (2)	N2—C10—C9	118.8 (2)
C1—C2—C3	120.8 (3)	C16—C11—C12	118.9 (3)
C1—C2—H2	119.6	C16—C11—N2	118.3 (2)
C3—C2—H2	119.6	C12—C11—N2	122.7 (2)
C4—C3—C2	120.1 (3)	C13—C12—C11	119.8 (2)
C4—C3—H3	120.0	C13—C12—H12	120.1
C2—C3—H3	120.0	C11—C12—H12	120.1
C5—C4—C3	119.3 (3)	C14—C13—C12	120.8 (3)
C5—C4—H4	120.3	C14—C13—H13	119.6
C3—C4—H4	120.3	C12—C13—H13	119.6
C4—C5—C6	121.3 (3)	C13—C14—C15	119.4 (3)
C4—C5—H5	119.3	C13—C14—H14	120.3
C6—C5—H5	119.3	C15—C14—H14	120.3
C1—C6—C5	119.0 (3)	C16—C15—C14	121.0 (3)
C1—C6—H6	120.5	C16—C15—H15	119.5
C5—C6—H6	120.5	C14—C15—H15	119.5
O1—C7—N1	122.9 (2)	C15—C16—C11	120.1 (3)
O1—C7—C8	124.8 (2)	C15—C16—H16	120.0
N1—C7—C8	112.3 (2)	C11—C16—H16	120.0
C9—C8—C7	130.1 (3)	C7—N1—C1	129.0 (2)
C9—C8—H8	114.9	C7—N1—H1N	119.9 (18)
C7—C8—H8	114.9	C1—N1—H1N	111.1 (18)
C8—C9—C10	135.5 (2)	C10—N2—C11	126.0 (2)
C8—C9—H9	112.3	C10—N2—H2N	114.2 (19)
C10—C9—H9	112.3	C11—N2—H2N	119.8 (18)
C6—C1—C2—C3	−0.1 (5)	C11—C12—C13—C14	−0.5 (5)
N1—C1—C2—C3	−179.4 (2)	C12—C13—C14—C15	−0.3 (5)
C1—C2—C3—C4	−0.3 (5)	C13—C14—C15—C16	0.5 (5)
C2—C3—C4—C5	0.5 (5)	C14—C15—C16—C11	0.0 (5)
C3—C4—C5—C6	−0.4 (6)	C12—C11—C16—C15	−0.7 (4)
C2—C1—C6—C5	0.2 (4)	N2—C11—C16—C15	−176.6 (3)
N1—C1—C6—C5	179.5 (2)	O1—C7—N1—C1	1.8 (5)
C4—C5—C6—C1	0.0 (5)	C8—C7—N1—C1	−177.7 (2)
O1—C7—C8—C9	−3.9 (5)	C2—C1—N1—C7	174.4 (3)
N1—C7—C8—C9	175.6 (3)	C6—C1—N1—C7	−4.9 (4)
C7—C8—C9—C10	0.5 (6)	O2—C10—N2—C11	−1.7 (4)
C8—C9—C10—O2	−179.8 (3)	C9—C10—N2—C11	178.8 (3)
C8—C9—C10—N2	−0.3 (6)	C16—C11—N2—C10	−143.9 (3)
C16—C11—C12—C13	1.0 (4)	C12—C11—N2—C10	40.4 (4)
N2—C11—C12—C13	176.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.86 (2)	2.04 (2)	2.884 (3)	167 (2)
N2—H2N···O1	0.91 (2)	1.77 (2)	2.671 (3)	167 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.86 (2)	2.04 (2)	2.884 (3)	167 (2)
N2—H2N⋯O1	0.91 (2)	1.77 (2)	2.671 (3)	167 (3)

Symmetry code: (i) .