(E)-2-[(2-Formyl­phen­oxy)meth­yl]-3-(4-iso­propyl­phen­yl)acrylo­nitrile

Kanchanadevi, J.; Anbalagan, G.; Selvakumar, R.; Bakthadoss, M.; Gunasekaran, B.; Manivannan, V.

doi:10.1107/S1600536813020618

organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1354

doi:10.1107/S1600536813020618

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(E)-2-[(2-Formylphenoxy)methyl]-3-(4-isopropylphenyl)acrylonitrile

J. Kanchanadevi,^a G. Anbalagan,^b R. Selvakumar,^c M. Bakthadoss,^c B. Gunasekaran ^d and V. Manivannan ^e ^*

^aDepartment of Physics, Velammal Institute of Technology, Panchetty, Chennai 601 204, India, ^bDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, ^cDepartment of Organic Chemistry, University of Madras, Guindy campus, Chennai 600 025, India, ^dDepartment of Physics & Nano Technology, SRM University, SRM Nagar, Kattankulathur, Kancheepuram Dist, Chennai 603 203, Tamil Nadu, India, and ^eDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
^*Correspondence e-mail: phdguna@gmail.com, crystallography2010@gmail.com

(Received 13 July 2013; accepted 24 July 2013; online 31 July 2013)

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, molecules are linked through a weak C—H⋯O interaction, 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_r = 305.36
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.056
wR(F²) = 0.179
S = 1.09
3532 reflections
231 parameters
12 restraints
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.18 e Å⁻³

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) $[x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S1600536813020618/is5291sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536813020618/is5291Isup3.cml

checkCIF report

Comment top

Cyanoacrylates and its derivatives have been widely used as agrochemicals (Zhang et al., 2009) and an important intermediate in drugs synthesis (Obniska et al., 2005).

The geometric parameters of the title molecule (Fig. 1) agree well with reported similar structure(Ye et al., 2009; Suresh et al., 2012; Govindan et al., 2012). The dihedral angle between the two benzene rings (C1—C6 & C10—C15) is 77.12 (8)°. The terminal methyl groups are disordered over two positions with the site occupancies of C17 = 0.280 (14) and C17A = 0.720 (14), C18 = 0.280 (14) and C18A = 0.720 (14). The crystal packing is through a weak intermolecular C—H···O interaction.

Related literature top

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 top

A solution of salicylaldehyde (1 equivalent) and potassium carbonate (1 equivalent) in acetonitrile solvent was stirred for 15 minutes at room temperature. To this solution, (Z)-methyl 2-(bromomethyl)-3-(4-isopropylphenyl)acrylate (1 equivalent) was added dropwise. After the completion of the reaction as indicated by TLC, acetonitrile was evaporated. Ethylacetate (15 ml) and water (15 ml) were added to the crude mass and extracted. The organic layer was dried over anhydrous sodium sulfate. Removal of solvent led to the crude product which was purified through pad of silica gel (100–200 mesh) using ethylacetate and hexane (1:9) as solvents. The pure title compound was obtained as colorless solid (94%). Recrystallization was carried out using ethylacetate as solvent.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. A packing diagram of the title compound, viewed down the b axis. Hydrogen bonds are shown as dashed lines.

(E)-2-[(2-Formylphenoxy)methyl]-3-(4-isopropylphenyl)acrylonitrile top

Crystal data top

C₂₀H₁₉NO₂	F(000) = 648
M_r = 305.36	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.074P)² + 0.3076P] where P = (F_o² + 2F_c²)/3
3532 reflections	(Δ/σ)_max = 0.013
231 parameters	Δρ_max = 0.32 e Å⁻³
12 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₀H₁₉NO₂	V = 1728.5 (2) Å³
M_r = 305.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.3276 (9) Å	µ = 0.08 mm⁻¹
b = 11.6435 (7) Å	T = 295 K
c = 11.9965 (9) Å	0.30 × 0.25 × 0.20 mm
β = 111.800 (3)°

Data collection top

Bruker APEXII CCD diffractometer	3532 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2004 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.985	R_int = 0.025
16125 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	12 restraints
wR(F²) = 0.179	H-atom parameters constrained
S = 1.09	Δρ_max = 0.32 e Å⁻³
3532 reflections	Δρ_min = −0.18 e Å⁻³
231 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, −y−1/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

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) x, −y−1/2, z+1/2.

References

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Volume 69| Part 8| August 2013| Page o1354

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