N-Benzyl-N-(4-chloro-phen-yl)acrylamide.

In the mol-ecular structure of the title compound, C(16)H(14)ClNO, the acrylamide unit is essentially planar and makes dihedral angles of 80.06 (12) and 68.91 (13)°, respectively, with the benzene and phenyl rings. The dihedral angle between the two rings is 49.79 (11)°. In the crystal structure, mol-ecules are connected via weak C-H⋯O and C-H⋯π inter-actions, forming a mol-ecular tape running along the b axis.

Related literature

For related literature, see: Fairlamb (2004 ▶); Hu et al. (2003 ▶); Park & Hoffmann (1990 ▶); Otero & Cantero (1995 ▶); Riggi et al. (1992 ▶).

Experimental

Crystal data

C16H14ClNO

M = 271.73

Monoclinic,

a = 9.215 (4) Å

b = 9.210 (4) Å

c = 17.090 (8) Å

β = 102.842 (6)°

V = 1414.2 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 291 (2) K

0.30 × 0.26 × 0.24 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2000 ▶) T min = 0.93, T max = 0.94

11395 measured reflections

3172 independent reflections

1666 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.158

S = 1.06

3172 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT-Plus (Bruker, 2000 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 2000 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680706432X/is2254sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680706432X/is2254Isup2.hkl

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

C16H14ClNO	F000 = 568
Mr = 271.73	Dx = 1.276 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3741 reflections
a = 9.215 (4) Å	θ = 2.1–25.4º
b = 9.210 (4) Å	µ = 0.26 mm−1
c = 17.090 (8) Å	T = 291 (2) K
β = 102.842 (6)º	Block, colourless
V = 1414.2 (12) Å3	0.30 × 0.26 × 0.24 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	3172 independent reflections
Radiation source: sealed tube	1666 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.057
T = 291(2) K	θmax = 27.5º
φ and ω scans	θmin = 2.3º
Absorption correction: multi-scan(SADABS; Bruker, 2000)	h = −11→11
Tmin = 0.93, Tmax = 0.94	k = −11→11
11395 measured reflections	l = −20→22

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.064	w = 1/[σ2(Fo2) + (0.05P)2 + 0.55P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.158	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.30 e Å−3
3172 reflections	Δρmin = −0.28 e Å−3
173 parameters	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.008 (2)
Secondary atom site location: difference Fourier map

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.Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)9.0764 (0.0047) x - 0.6878 (0.0111) y - 1.1393 (0.0196) z = 0.3034 (0.0082)* -0.0078 (0.0020) C1 * 0.0033 (0.0020) C2 * 0.0052 (0.0021) C3 * -0.0091 (0.0020) C4 * 0.0045 (0.0020) C5 * 0.0039 (0.0020) C6Rms deviation of fitted atoms = 0.00604.7161 (0.0105) x - 5.4299 (0.0094) y + 8.4686 (0.0192) z = 4.7812 (0.0131)Angle to previous plane (with approximate e.s.d.) = 49.79 (0.11)* 0.0026 (0.0019) C8 * 0.0023 (0.0020) C9 * -0.0059 (0.0022) C10 * 0.0046 (0.0023) C11 * 0.0004 (0.0023) C12 * -0.0040 (0.0021) C13Rms deviation of fitted atoms = 0.0037

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	0.1090 (3)	0.2996 (3)	0.42821 (14)	0.0487 (7)
C2	0.0953 (3)	0.2145 (3)	0.36048 (15)	0.0586 (8)
H2	0.0888	0.1141	0.3641	0.070*
C3	0.0913 (3)	0.2801 (3)	0.28706 (15)	0.0623 (8)
H3	0.0824	0.2240	0.2410	0.075*
C4	0.1004 (3)	0.4277 (3)	0.28296 (15)	0.0561 (7)
C5	0.1168 (3)	0.5138 (3)	0.35022 (16)	0.0586 (7)
H5	0.1250	0.6141	0.3466	0.070*
C6	0.1209 (3)	0.4476 (3)	0.42326 (16)	0.0565 (7)
H6	0.1318	0.5039	0.4694	0.068*
C7	0.2646 (3)	0.2115 (3)	0.55720 (15)	0.0607 (8)
H7A	0.3338	0.1858	0.5242	0.073*
H7B	0.2612	0.1311	0.5934	0.073*
C8	0.3224 (3)	0.3442 (3)	0.60604 (15)	0.0524 (7)
C9	0.4397 (3)	0.4235 (3)	0.59152 (16)	0.0606 (8)
H9	0.4840	0.3961	0.5499	0.073*
C10	0.4933 (4)	0.5435 (4)	0.63763 (19)	0.0716 (9)
H10	0.5720	0.5966	0.6264	0.086*
C11	0.4310 (4)	0.5840 (4)	0.69955 (19)	0.0747 (9)
H11	0.4680	0.6637	0.7312	0.090*
C12	0.3137 (4)	0.5065 (4)	0.71468 (19)	0.0776 (10)
H12	0.2704	0.5342	0.7566	0.093*
C13	0.2590 (3)	0.3874 (3)	0.66831 (16)	0.0641 (8)
H13	0.1788	0.3360	0.6791	0.077*
C14	−0.0055 (3)	0.1827 (3)	0.52919 (16)	0.0569 (7)
C15	−0.1547 (4)	0.2031 (3)	0.47419 (17)	0.0622 (8)
H15	−0.1607	0.2433	0.4237	0.075*
C16	−0.2751 (4)	0.1660 (4)	0.4955 (2)	0.0807 (10)
H16A	−0.2702	0.1258	0.5459	0.097*
H16B	−0.3669	0.1796	0.4604	0.097*
Cl1	0.09117 (12)	0.51004 (11)	0.18992 (5)	0.0938 (4)
N1	0.1152 (3)	0.2311 (2)	0.50484 (12)	0.0537 (6)
O1	0.0044 (3)	0.1269 (2)	0.59589 (12)	0.0769 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0522 (16)	0.0546 (17)	0.0341 (13)	−0.0008 (13)	−0.0014 (12)	−0.0025 (11)
C2	0.074 (2)	0.0544 (17)	0.0410 (15)	−0.0033 (15)	−0.0019 (14)	−0.0061 (12)
C3	0.073 (2)	0.073 (2)	0.0352 (15)	−0.0065 (16)	0.0005 (14)	−0.0101 (13)
C4	0.0506 (17)	0.074 (2)	0.0385 (15)	−0.0049 (14)	−0.0020 (13)	0.0064 (13)
C5	0.0630 (19)	0.0550 (17)	0.0540 (17)	−0.0017 (14)	0.0053 (14)	0.0020 (13)
C6	0.0683 (19)	0.0553 (18)	0.0420 (15)	0.0004 (14)	0.0036 (14)	−0.0072 (13)
C7	0.0650 (19)	0.0652 (19)	0.0442 (15)	0.0101 (15)	−0.0045 (14)	0.0000 (13)
C8	0.0536 (17)	0.0630 (18)	0.0326 (13)	0.0028 (14)	−0.0074 (12)	0.0008 (12)
C9	0.0597 (19)	0.077 (2)	0.0411 (15)	0.0046 (17)	0.0035 (14)	0.0050 (14)
C10	0.060 (2)	0.081 (2)	0.066 (2)	−0.0098 (17)	−0.0038 (17)	0.0063 (17)
C11	0.069 (2)	0.085 (2)	0.060 (2)	−0.0075 (19)	−0.0065 (17)	−0.0151 (17)
C12	0.079 (2)	0.099 (3)	0.0520 (18)	−0.004 (2)	0.0088 (17)	−0.0219 (17)
C13	0.0554 (18)	0.085 (2)	0.0488 (17)	−0.0074 (16)	0.0057 (14)	−0.0068 (15)
C14	0.074 (2)	0.0511 (17)	0.0410 (15)	−0.0084 (15)	0.0031 (15)	−0.0050 (12)
C15	0.068 (2)	0.0663 (19)	0.0489 (17)	−0.0113 (16)	0.0054 (15)	−0.0012 (14)
C16	0.061 (2)	0.0653 (2)	0.053 (2)	−0.009 (2)	0.0097 (19)	−0.0015 (18)
Cl1	0.1158 (8)	0.1115 (8)	0.0498 (5)	−0.0131 (6)	0.0093 (5)	0.0202 (5)
N1	0.0605 (15)	0.0593 (15)	0.0345 (11)	−0.0032 (12)	−0.0044 (11)	−0.0001 (10)
O1	0.0958 (17)	0.0819 (15)	0.0480 (12)	−0.0129 (12)	0.0052 (11)	0.0133 (11)

C1—C6	1.372 (4)	C8—C13	1.382 (4)
C1—C2	1.380 (3)	C9—C10	1.383 (4)
C1—N1	1.443 (3)	C9—H9	0.9300
C2—C3	1.386 (4)	C10—C11	1.363 (4)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.365 (4)	C11—C12	1.367 (5)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.376 (4)	C12—C13	1.381 (4)
C4—Cl1	1.747 (3)	C12—H12	0.9300
C5—C6	1.382 (4)	C13—H13	0.9300
C5—H5	0.9300	C14—O1	1.235 (3)
C6—H6	0.9300	C14—N1	1.347 (4)
C7—N1	1.476 (3)	C14—C15	1.495 (4)
C7—C8	1.509 (4)	C15—C16	1.288 (4)
C7—H7A	0.9700	C15—H15	0.9300
C7—H7B	0.9700	C16—H16A	0.9300
C8—C9	1.371 (4)	C16—H16B	0.9300
C6—C1—C2	120.4 (2)	C8—C9—C10	121.2 (3)
C6—C1—N1	120.2 (2)	C8—C9—H9	119.4
C2—C1—N1	119.4 (2)	C10—C9—H9	119.4
C1—C2—C3	119.4 (3)	C11—C10—C9	120.1 (3)
C1—C2—H2	120.3	C11—C10—H10	119.9
C3—C2—H2	120.3	C9—C10—H10	119.9
C4—C3—C2	119.4 (3)	C10—C11—C12	119.4 (3)
C4—C3—H3	120.3	C10—C11—H11	120.3
C2—C3—H3	120.3	C12—C11—H11	120.3
C3—C4—C5	121.8 (3)	C11—C12—C13	120.6 (3)
C3—C4—Cl1	119.2 (2)	C11—C12—H12	119.7
C5—C4—Cl1	119.0 (2)	C13—C12—H12	119.7
C4—C5—C6	118.4 (3)	C12—C13—C8	120.5 (3)
C4—C5—H5	120.8	C12—C13—H13	119.8
C6—C5—H5	120.8	C8—C13—H13	119.8
C1—C6—C5	120.5 (3)	O1—C14—N1	121.7 (3)
C1—C6—H6	119.8	O1—C14—C15	120.1 (3)
C5—C6—H6	119.8	N1—C14—C15	118.1 (2)
N1—C7—C8	113.8 (2)	C16—C15—C14	121.3 (3)
N1—C7—H7A	108.8	C16—C15—H15	119.4
C8—C7—H7A	108.8	C14—C15—H15	119.4
N1—C7—H7B	108.8	C15—C16—H16A	120.0
C8—C7—H7B	108.8	C15—C16—H16B	120.0
H7A—C7—H7B	107.7	H16A—C16—H16B	120.0
C9—C8—C13	118.1 (3)	C14—N1—C1	123.8 (2)
C9—C8—C7	121.8 (3)	C14—N1—C7	119.7 (2)
C13—C8—C7	120.1 (3)	C1—N1—C7	116.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.93	2.53	3.405 (4)	157
C6—H6···Cg1ii	0.93	3.02	3.75 (2)	136

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the mid-point of atoms C15 and C16.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.93	2.53	3.405 (4)	157
C6—H6⋯Cg1ii	0.93	3.02	3.75 (2)	136

Symmetry codes: (i) ; (ii) . Cg1 is the mid-point of atoms C15 and C16.