(E)-2-[(2-Formyl-phen-oxy)meth-yl]-3-(4-iso-propyl-phen-yl)acrylo-nitrile.

In the title compound, C20H19NO2, the dihedral angle between the benzene rings is 77.12 (8)°. The terminal isopropyl group is disordered over two orientations, with site occupancies of 0.720 (14) and 0.280 (14). In the crystal, mol-ecules are linked through a weak C-H⋯O inter-action, forming a zigzag chain along the c-axis direction.

Related literature

For the biological activity of cyano­acrylates, see: Zhang et al. (2009 ▶); Obniska et al. (2005 ▶). For related structures, see: Ye et al. (2009 ▶); Suresh et al. (2012 ▶); Govindan et al. (2012 ▶).

Experimental

Crystal data

C20H19NO2

M = 305.36

Monoclinic,

a = 13.3276 (9) Å

b = 11.6435 (7) Å

c = 11.9965 (9) Å

β = 111.800 (3)°

V = 1728.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.977, T max = 0.985

16125 measured reflections

3532 independent reflections

2004 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.179

S = 1.09

3532 reflections

231 parameters

12 restraints

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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 datablock(s) I. DOI: 10.1107/S1600536813020618/is5291sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813020618/is5291Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813020618/is5291Isup3.cml

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

C20H19NO2	F(000) = 648
Mr = 305.36	Dx = 1.173 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3895 reflections
a = 13.3276 (9) Å	θ = 2.4–26.4°
b = 11.6435 (7) Å	µ = 0.08 mm−1
c = 11.9965 (9) Å	T = 295 K
β = 111.800 (3)°	Block, colourless
V = 1728.5 (2) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker APEXII CCD diffractometer	3532 independent reflections
Radiation source: fine-focus sealed tube	2004 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 0 pixels mm-1	θmax = 26.4°, θmin = 2.4°
ω and φ scans	h = −16→15
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −9→14
Tmin = 0.977, Tmax = 0.985	l = −15→14
16125 measured reflections

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.074P)2 + 0.3076P] where P = (Fo2 + 2Fc2)/3
3532 reflections	(Δ/σ)max = 0.013
231 parameters	Δρmax = 0.32 e Å−3
12 restraints	Δρmin = −0.18 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.55620 (17)	−0.06955 (16)	0.3043 (2)	0.0650 (6)
C2	0.5111 (2)	−0.16986 (18)	0.3262 (2)	0.0789 (7)
H2	0.4677	−0.2142	0.2619	0.095*
C3	0.5290 (2)	−0.2047 (2)	0.4401 (3)	0.0913 (8)
H3	0.4977	−0.2720	0.4536	0.110*
C4	0.5937 (2)	−0.1397 (2)	0.5349 (2)	0.0878 (7)
H4	0.6065	−0.1642	0.6128	0.105*
C5	0.64009 (19)	−0.0388 (2)	0.5171 (2)	0.0777 (6)
H5	0.6837	0.0046	0.5822	0.093*
C6	0.62042 (17)	−0.00323 (17)	0.40049 (19)	0.0635 (5)
C7	0.7365 (2)	0.16085 (19)	0.4660 (2)	0.0791 (7)
H7A	0.7974	0.1128	0.5116	0.095*
H7B	0.7036	0.1903	0.5200	0.095*
C8	0.77323 (18)	0.25785 (18)	0.4086 (2)	0.0725 (6)
C9	0.76564 (19)	0.36663 (19)	0.4379 (2)	0.0759 (6)
H9	0.7331	0.3771	0.4935	0.091*
C10	0.79995 (19)	0.47258 (18)	0.3971 (2)	0.0716 (6)
C11	0.8839 (2)	0.4797 (2)	0.3558 (3)	0.0899 (8)
H11	0.9195	0.4132	0.3482	0.108*
C12	0.9151 (2)	0.5837 (2)	0.3258 (3)	0.0987 (9)
H12	0.9723	0.5859	0.2991	0.118*
C13	0.8652 (2)	0.6843 (2)	0.3339 (2)	0.0886 (8)
C14	0.7801 (2)	0.6776 (2)	0.3723 (2)	0.0923 (8)
H14	0.7429	0.7441	0.3760	0.111*
C15	0.7491 (2)	0.5741 (2)	0.4052 (2)	0.0852 (7)
H15	0.6929	0.5725	0.4335	0.102*
C16	0.9055 (3)	0.7981 (2)	0.3044 (3)	0.1238 (10)
H16A	0.9825	0.7830	0.3239	0.149*	0.280 (14)
H16B	0.9563	0.7792	0.2653	0.149*	0.720 (14)
C17	0.8674 (13)	0.8319 (18)	0.1750 (6)	0.168 (8)	0.280 (14)
H17A	0.9165	0.8870	0.1640	0.252*	0.280 (14)
H17B	0.7967	0.8652	0.1512	0.252*	0.280 (14)
H17C	0.8646	0.7652	0.1269	0.252*	0.280 (14)
C18	0.9075 (17)	0.8975 (11)	0.3860 (14)	0.158 (7)	0.280 (14)
H18A	0.9376	0.8725	0.4681	0.237*	0.280 (14)
H18B	0.8351	0.9247	0.3680	0.237*	0.280 (14)
H18C	0.9509	0.9584	0.3738	0.237*	0.280 (14)
C18A	0.9463 (8)	0.8730 (6)	0.4109 (6)	0.222 (5)	0.720 (14)
H18D	0.9905	0.9324	0.3975	0.333*	0.720 (14)
H18E	0.9886	0.8283	0.4796	0.333*	0.720 (14)
H18F	0.8865	0.9069	0.4250	0.333*	0.720 (14)
C17A	0.8161 (7)	0.8571 (7)	0.2060 (7)	0.230 (6)	0.720 (14)
H17D	0.7543	0.8641	0.2284	0.344*	0.720 (14)
H17E	0.7971	0.8129	0.1335	0.344*	0.720 (14)
H17F	0.8396	0.9321	0.1931	0.344*	0.720 (14)
C19	0.5360 (2)	−0.0363 (2)	0.1806 (2)	0.0807 (7)
H19	0.5687	0.0304	0.1678	0.097*
N1	0.8430 (3)	0.1946 (2)	0.2453 (3)	0.1215 (9)
C20	0.8136 (2)	0.2253 (2)	0.3180 (3)	0.0851 (7)
O1	0.65982 (13)	0.09621 (12)	0.37184 (13)	0.0776 (5)
O2	0.47952 (17)	−0.08980 (16)	0.09395 (17)	0.1076 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0713 (13)	0.0488 (11)	0.0771 (14)	0.0039 (10)	0.0303 (11)	0.0005 (10)
C2	0.0840 (16)	0.0558 (13)	0.0971 (18)	−0.0030 (11)	0.0340 (13)	0.0002 (12)
C3	0.0973 (19)	0.0639 (15)	0.117 (2)	−0.0050 (14)	0.0445 (17)	0.0178 (15)
C4	0.0975 (18)	0.0803 (17)	0.0898 (18)	0.0110 (15)	0.0396 (15)	0.0307 (14)
C5	0.0841 (16)	0.0692 (15)	0.0744 (15)	0.0010 (12)	0.0231 (12)	0.0090 (11)
C6	0.0716 (13)	0.0481 (11)	0.0716 (14)	0.0064 (10)	0.0274 (11)	0.0078 (10)
C7	0.0967 (17)	0.0662 (14)	0.0671 (14)	−0.0158 (12)	0.0218 (12)	−0.0022 (11)
C8	0.0844 (15)	0.0597 (13)	0.0679 (13)	−0.0100 (11)	0.0219 (12)	−0.0026 (10)
C9	0.0844 (15)	0.0643 (14)	0.0776 (15)	−0.0101 (12)	0.0286 (12)	−0.0049 (11)
C10	0.0784 (15)	0.0560 (13)	0.0769 (14)	−0.0072 (11)	0.0250 (12)	−0.0054 (10)
C11	0.0912 (18)	0.0581 (14)	0.128 (2)	−0.0027 (12)	0.0492 (17)	−0.0043 (13)
C12	0.105 (2)	0.0661 (16)	0.146 (3)	−0.0101 (14)	0.071 (2)	−0.0057 (15)
C13	0.0998 (19)	0.0587 (15)	0.115 (2)	−0.0108 (13)	0.0488 (16)	−0.0037 (13)
C14	0.1020 (19)	0.0552 (14)	0.124 (2)	0.0000 (13)	0.0466 (17)	−0.0065 (13)
C15	0.0939 (17)	0.0669 (15)	0.1036 (19)	−0.0067 (13)	0.0468 (15)	−0.0088 (13)
C16	0.161 (3)	0.0624 (16)	0.180 (3)	−0.0003 (17)	0.101 (2)	0.0119 (16)
C17	0.130 (12)	0.218 (19)	0.161 (5)	−0.096 (12)	0.060 (8)	0.002 (8)
C18	0.25 (2)	0.081 (7)	0.209 (13)	0.058 (11)	0.160 (16)	0.023 (7)
C18A	0.260 (9)	0.100 (4)	0.178 (4)	−0.115 (6)	−0.066 (6)	0.022 (3)
C17A	0.268 (9)	0.191 (7)	0.136 (5)	−0.145 (6)	−0.034 (5)	0.096 (5)
C19	0.0988 (18)	0.0642 (14)	0.0810 (17)	−0.0059 (13)	0.0354 (14)	−0.0101 (12)
N1	0.174 (3)	0.0914 (17)	0.124 (2)	−0.0213 (17)	0.084 (2)	−0.0193 (15)
C20	0.111 (2)	0.0588 (14)	0.0874 (17)	−0.0155 (13)	0.0386 (16)	−0.0045 (13)
O1	0.0981 (11)	0.0565 (9)	0.0699 (9)	−0.0167 (8)	0.0214 (8)	0.0037 (7)
O2	0.1335 (17)	0.1036 (14)	0.0868 (13)	−0.0221 (12)	0.0422 (12)	−0.0279 (10)

C1—C2	1.383 (3)	C13—C14	1.376 (4)
C1—C6	1.388 (3)	C13—C16	1.520 (3)
C1—C19	1.459 (3)	C14—C15	1.379 (3)
C2—C3	1.359 (3)	C14—H14	0.9300
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.371 (4)	C16—C18A	1.474 (4)
C3—H3	0.9300	C16—C17	1.495 (5)
C4—C5	1.381 (3)	C16—C17A	1.497 (4)
C4—H4	0.9300	C16—C18	1.510 (5)
C5—C6	1.388 (3)	C16—H16A	0.9800
C5—H5	0.9300	C16—H16B	0.9800
C6—O1	1.367 (2)	C17—H17A	0.9600
C7—O1	1.425 (3)	C17—H17B	0.9600
C7—C8	1.496 (3)	C17—H17C	0.9600
C7—H7A	0.9700	C18—H18A	0.9600
C7—H7B	0.9700	C18—H18B	0.9600
C8—C9	1.328 (3)	C18—H18C	0.9600
C8—C20	1.432 (4)	C18A—H18D	0.9600
C9—C10	1.462 (3)	C18A—H18E	0.9600
C9—H9	0.9300	C18A—H18F	0.9600
C10—C15	1.384 (3)	C17A—H17D	0.9600
C10—C11	1.384 (3)	C17A—H17E	0.9600
C11—C12	1.371 (3)	C17A—H17F	0.9600
C11—H11	0.9300	C19—O2	1.206 (3)
C12—C13	1.368 (3)	C19—H19	0.9300
C12—H12	0.9300	N1—C20	1.138 (3)
C2—C1—C6	119.3 (2)	C13—C14—H14	119.4
C2—C1—C19	119.3 (2)	C15—C14—H14	119.4
C6—C1—C19	121.45 (19)	C14—C15—C10	121.3 (2)
C3—C2—C1	121.1 (2)	C14—C15—H15	119.3
C3—C2—H2	119.5	C10—C15—H15	119.3
C1—C2—H2	119.5	C18A—C16—C17A	109.9 (4)
C2—C3—C4	119.4 (2)	C17—C16—C18	112.9 (7)
C2—C3—H3	120.3	C18A—C16—C13	111.2 (4)
C4—C3—H3	120.3	C17—C16—C13	117.3 (8)
C3—C4—C5	121.4 (2)	C17A—C16—C13	109.7 (3)
C3—C4—H4	119.3	C18—C16—C13	116.1 (7)
C5—C4—H4	119.3	C18A—C16—H16A	83.2
C4—C5—C6	118.8 (2)	C17—C16—H16A	102.6
C4—C5—H5	120.6	C17A—C16—H16A	136.7
C6—C5—H5	120.6	C18—C16—H16A	102.6
O1—C6—C5	124.0 (2)	C13—C16—H16A	102.6
O1—C6—C1	115.98 (18)	C18A—C16—H16B	116.7
C5—C6—C1	120.0 (2)	C17A—C16—H16B	102.4
O1—C7—C8	107.17 (18)	C13—C16—H16B	106.4
O1—C7—H7A	110.3	C16—C17—H17A	109.5
C8—C7—H7A	110.3	C16—C17—H17B	109.5
O1—C7—H7B	110.3	C16—C17—H17C	109.5
C8—C7—H7B	110.3	C16—C18—H18A	109.5
H7A—C7—H7B	108.5	C16—C18—H18B	109.5
C9—C8—C20	122.7 (2)	C16—C18—H18C	109.5
C9—C8—C7	121.9 (2)	C16—C18A—H18D	109.5
C20—C8—C7	115.40 (19)	C16—C18A—H18E	109.5
C8—C9—C10	130.7 (2)	H18D—C18A—H18E	109.5
C8—C9—H9	114.6	C16—C18A—H18F	109.5
C10—C9—H9	114.6	H18D—C18A—H18F	109.5
C15—C10—C11	117.1 (2)	H18E—C18A—H18F	109.5
C15—C10—C9	118.4 (2)	C16—C17A—H17D	109.5
C11—C10—C9	124.4 (2)	C16—C17A—H17E	109.5
C12—C11—C10	120.7 (2)	H17D—C17A—H17E	109.5
C12—C11—H11	119.6	C16—C17A—H17F	109.5
C10—C11—H11	119.6	H17D—C17A—H17F	109.5
C13—C12—C11	122.4 (2)	H17E—C17A—H17F	109.5
C13—C12—H12	118.8	O2—C19—C1	124.0 (2)
C11—C12—H12	118.8	O2—C19—H19	118.0
C12—C13—C14	117.2 (2)	C1—C19—H19	118.0
C12—C13—C16	120.5 (2)	N1—C20—C8	176.6 (3)
C14—C13—C16	122.3 (2)	C6—O1—C7	118.54 (16)
C13—C14—C15	121.2 (2)
C6—C1—C2—C3	−0.3 (3)	C11—C12—C13—C14	−0.8 (5)
C19—C1—C2—C3	179.2 (2)	C11—C12—C13—C16	177.6 (3)
C1—C2—C3—C4	−0.5 (4)	C12—C13—C14—C15	2.2 (4)
C2—C3—C4—C5	0.8 (4)	C16—C13—C14—C15	−176.1 (3)
C3—C4—C5—C6	−0.1 (4)	C13—C14—C15—C10	−2.2 (4)
C4—C5—C6—O1	178.4 (2)	C11—C10—C15—C14	0.7 (4)
C4—C5—C6—C1	−0.8 (3)	C9—C10—C15—C14	177.7 (2)
C2—C1—C6—O1	−178.29 (18)	C12—C13—C16—C18A	−115.9 (6)
C19—C1—C6—O1	2.2 (3)	C14—C13—C16—C18A	62.4 (7)
C2—C1—C6—C5	1.0 (3)	C12—C13—C16—C17	83.0 (9)
C19—C1—C6—C5	−178.5 (2)	C14—C13—C16—C17	−98.7 (9)
O1—C7—C8—C9	124.1 (2)	C12—C13—C16—C17A	122.2 (6)
O1—C7—C8—C20	−54.1 (3)	C14—C13—C16—C17A	−59.5 (7)
C20—C8—C9—C10	−4.7 (4)	C12—C13—C16—C18	−139.3 (10)
C7—C8—C9—C10	177.3 (2)	C14—C13—C16—C18	39.0 (10)
C8—C9—C10—C15	156.3 (3)	C2—C1—C19—O2	1.7 (4)
C8—C9—C10—C11	−26.9 (4)	C6—C1—C19—O2	−178.8 (2)
C15—C10—C11—C12	0.7 (4)	C5—C6—O1—C7	8.2 (3)
C9—C10—C11—C12	−176.1 (2)	C1—C6—O1—C7	−172.53 (19)
C10—C11—C12—C13	−0.7 (5)	C8—C7—O1—C6	174.72 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2i	0.93	2.41	3.236 (3)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2i	0.93	2.41	3.236 (3)	149

Symmetry code: (i) .