Literature DB >> 22412487

(E)-2-({2-[(E)-(Hy-droxy-imino)-meth-yl]phen-oxy}meth-yl)-3-p-tolyl-acrylonitrile.

G Suresh, V Sabari, J Srinivasan, Bakthadoss Mannickam, S Aravindhan.

Abstract

In the title compound, C(18)H(16)N(2)O(2), the hy-droxy-ethanimine group is essentially coplanar with the ring to which it is attached (C-C-N-O torsion angle = -176.9°). Mol-ecules are linked into cyclic centrosymmetric R(2) (2)(6) dimers via O-H⋯N hydrogen bonds.

Entities: Chemical Disease Gene

Year: 2012 PMID： 22412487 PMCID： PMC3297297 DOI： 10.1107/S160053681200270X

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For the structures of other acrylate derivatives, see: Zhang et al. (2009 ▶); Wang et al. (2011 ▶); SakthiMurugesan et al. (2011 ▶); Govindan et al. (2011 ▶). For the use of oxime ligands in coordination chemistry, see: Chaudhuri (2003 ▶). For the biological activity of caffeic acids, see: Hwang et al. (2001 ▶); Altug et al. (2008 ▶); Ates et al. (2006 ▶); Atik et al. (2006 ▶); Padinchare et al. (2001 ▶).

Experimental

Crystal data

C18H16N2O2 M = 292.33 Triclinic, a = 8.4851 (2) Å b = 9.3900 (3) Å c = 10.0779 (3) Å α = 100.208 (2)° β = 90.725 (1)° γ = 105.206 (1)° V = 761.10 (4) Å3 Z = 2 Mo Kα radiation μ = 0.08 mm−1 T = 293 K 0.2 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur-S diffractometer Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.980, T max = 0.990 18160 measured reflections 4229 independent reflections 3031 reflections with I > 2σ(I) R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.047 wR(F 2) = 0.151 S = 1.03 4229 reflections 201 parameters H-atom parameters constrained Δρmax = 0.24 e Å−3 Δρmin = −0.18 e Å−3 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 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681200270X/bt5756sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681200270X/bt5756Isup2.hkl Supplementary material file. DOI: 10.1107/S160053681200270X/bt5756Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₈H₁₆N₂O₂	Z = 2
M_r = 292.33	F(000) = 308
Triclinic, P1	D_x = 1.276 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4851 (2) Å	Cell parameters from 8725 reflections
b = 9.3900 (3) Å	θ = 2.8–29.1°
c = 10.0779 (3) Å	µ = 0.08 mm⁻¹
α = 100.208 (2)°	T = 293 K
β = 90.725 (1)°	Triclinic, colourless
γ = 105.206 (1)°	0.2 × 0.2 × 0.2 mm
V = 761.10 (4) Å³

Oxford Diffraction Xcalibur-S diffractometer	4229 independent reflections
Radiation source: fine-focus sealed tube	3031 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Detector resolution: 15.9948 pixels mm^-1	θ_max = 29.6°, θ_min = 2.1°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −12→12
T_min = 0.980, T_max = 0.990	l = −13→13
18160 measured reflections

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)] = 0.047	H-atom parameters constrained
wR(F²) = 0.151	w = 1/[σ²(F_o²) + (0.0732P)² + 0.135P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
4229 reflections	Δρ_max = 0.24 e Å⁻³
201 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0173 (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	U_iso*/U_eq
C1	0.2633 (2)	0.81093 (18)	1.11597 (16)	0.0584 (4)
H1	0.2024	0.8544	1.1791	0.070*
C2	0.22978 (17)	0.64825 (16)	1.09291 (13)	0.0453 (3)
C3	0.13864 (19)	0.57501 (19)	1.18740 (15)	0.0561 (4)
H3	0.1003	0.6318	1.2585	0.067*
C4	0.10362 (19)	0.42252 (19)	1.17926 (16)	0.0589 (4)
H4	0.0403	0.3767	1.2425	0.071*
C5	0.1631 (2)	0.33864 (18)	1.07685 (16)	0.0586 (4)
H5	0.1429	0.2356	1.0721	0.070*
C6	0.25320 (19)	0.40619 (16)	0.98021 (14)	0.0532 (3)
H6	0.2938	0.3482	0.9115	0.064*
C7	0.28343 (16)	0.55934 (15)	0.98496 (12)	0.0421 (3)
C8	0.3950 (2)	0.53835 (16)	0.76860 (13)	0.0522 (3)
H8A	0.3004	0.4535	0.7396	0.063*
H8B	0.4874	0.5003	0.7866	0.063*
C9	0.43216 (17)	0.63100 (15)	0.66042 (12)	0.0450 (3)
C10	0.29368 (19)	0.66178 (18)	0.60167 (15)	0.0559 (4)
C11	0.58348 (17)	0.67335 (15)	0.61876 (13)	0.0460 (3)
H11	0.6609	0.6433	0.6650	0.055*
C12	0.64990 (16)	0.75770 (15)	0.51448 (12)	0.0435 (3)
C13	0.81374 (17)	0.77192 (17)	0.48925 (14)	0.0495 (3)
H13	0.8746	0.7272	0.5380	0.059*
C14	0.88750 (18)	0.85082 (17)	0.39364 (15)	0.0549 (4)
H14	0.9974	0.8589	0.3795	0.066*
C15	0.80160 (19)	0.91823 (16)	0.31820 (14)	0.0536 (4)
C16	0.6389 (2)	0.9040 (2)	0.34270 (17)	0.0634 (4)
H16	0.5787	0.9487	0.2933	0.076*
C17	0.56333 (19)	0.8258 (2)	0.43805 (17)	0.0599 (4)
H17	0.4535	0.8182	0.4517	0.072*
C18	0.8817 (3)	1.0064 (2)	0.21478 (18)	0.0740 (5)
H18A	0.8424	0.9511	0.1258	0.111*
H18B	0.9982	1.0232	0.2247	0.111*
H18C	0.8558	1.1013	0.2278	0.111*
N1	0.36637 (16)	0.89828 (13)	1.05886 (12)	0.0535 (3)
N2	0.1784 (2)	0.6810 (2)	0.55663 (18)	0.0851 (5)
O1	0.37363 (18)	1.04895 (13)	1.10956 (14)	0.0795 (4)
H1A	0.4451	1.1035	1.0733	0.119*
O2	0.36281 (13)	0.63175 (10)	0.88863 (9)	0.0495 (3)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0724 (10)	0.0543 (9)	0.0521 (8)	0.0226 (7)	0.0238 (7)	0.0100 (7)
C2	0.0489 (7)	0.0495 (7)	0.0402 (6)	0.0151 (6)	0.0072 (5)	0.0123 (5)
C3	0.0607 (8)	0.0672 (10)	0.0479 (7)	0.0241 (7)	0.0193 (6)	0.0195 (7)
C4	0.0598 (9)	0.0687 (10)	0.0552 (8)	0.0151 (7)	0.0152 (7)	0.0322 (8)
C5	0.0720 (10)	0.0498 (8)	0.0534 (8)	0.0072 (7)	0.0059 (7)	0.0218 (7)
C6	0.0708 (9)	0.0444 (8)	0.0419 (7)	0.0102 (7)	0.0085 (6)	0.0091 (6)
C7	0.0475 (6)	0.0442 (7)	0.0330 (6)	0.0075 (5)	0.0036 (5)	0.0102 (5)
C8	0.0743 (9)	0.0423 (7)	0.0355 (6)	0.0098 (6)	0.0139 (6)	0.0035 (5)
C9	0.0583 (8)	0.0414 (7)	0.0322 (6)	0.0099 (6)	0.0098 (5)	0.0037 (5)
C10	0.0535 (8)	0.0653 (10)	0.0487 (8)	0.0125 (7)	0.0183 (6)	0.0147 (7)
C11	0.0536 (7)	0.0481 (7)	0.0361 (6)	0.0132 (6)	0.0034 (5)	0.0078 (5)
C12	0.0467 (7)	0.0444 (7)	0.0368 (6)	0.0085 (5)	0.0052 (5)	0.0059 (5)
C13	0.0479 (7)	0.0519 (8)	0.0467 (7)	0.0115 (6)	0.0030 (5)	0.0064 (6)
C14	0.0498 (7)	0.0533 (8)	0.0547 (8)	0.0060 (6)	0.0144 (6)	0.0031 (7)
C15	0.0655 (9)	0.0440 (7)	0.0430 (7)	0.0021 (6)	0.0115 (6)	0.0042 (6)
C16	0.0644 (9)	0.0693 (11)	0.0619 (9)	0.0150 (8)	0.0042 (7)	0.0307 (8)
C17	0.0475 (7)	0.0738 (11)	0.0657 (9)	0.0170 (7)	0.0114 (7)	0.0310 (8)
C18	0.0942 (13)	0.0603 (10)	0.0604 (10)	0.0033 (9)	0.0250 (9)	0.0171 (8)
N1	0.0721 (8)	0.0417 (6)	0.0470 (6)	0.0179 (6)	0.0113 (6)	0.0043 (5)
N2	0.0583 (9)	0.1209 (15)	0.0875 (11)	0.0292 (9)	0.0200 (8)	0.0404 (11)
O1	0.1108 (11)	0.0418 (6)	0.0846 (9)	0.0226 (6)	0.0388 (8)	0.0032 (6)
O2	0.0706 (6)	0.0383 (5)	0.0342 (4)	0.0058 (4)	0.0158 (4)	0.0051 (4)

C1—N1	1.2541 (19)	C10—N2	1.143 (2)
C1—C2	1.454 (2)	C11—C12	1.4578 (18)
C1—H1	0.9300	C11—H11	0.9300
C2—C3	1.3963 (19)	C12—C13	1.3923 (19)
C2—C7	1.4063 (17)	C12—C17	1.396 (2)
C3—C4	1.371 (2)	C13—C14	1.376 (2)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.369 (2)	C14—C15	1.382 (2)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.385 (2)	C15—C16	1.382 (2)
C5—H5	0.9300	C15—C18	1.504 (2)
C6—C7	1.3850 (19)	C16—C17	1.376 (2)
C6—H6	0.9300	C16—H16	0.9300
C7—O2	1.3670 (15)	C17—H17	0.9300
C8—O2	1.4371 (15)	C18—H18A	0.9600
C8—C9	1.4985 (19)	C18—H18B	0.9600
C8—H8A	0.9700	C18—H18C	0.9600
C8—H8B	0.9700	N1—O1	1.4013 (15)
C9—C11	1.3371 (19)	O1—H1A	0.8200
C9—C10	1.427 (2)

N1—C1—C2	126.24 (13)	C9—C11—C12	132.12 (13)
N1—C1—H1	116.9	C9—C11—H11	113.9
C2—C1—H1	116.9	C12—C11—H11	113.9
C3—C2—C7	117.57 (13)	C13—C12—C17	117.22 (13)
C3—C2—C1	116.91 (12)	C13—C12—C11	117.23 (12)
C7—C2—C1	125.51 (12)	C17—C12—C11	125.54 (12)
C4—C3—C2	122.44 (14)	C14—C13—C12	121.36 (13)
C4—C3—H3	118.8	C14—C13—H13	119.3
C2—C3—H3	118.8	C12—C13—H13	119.3
C5—C4—C3	119.14 (13)	C13—C14—C15	121.31 (13)
C5—C4—H4	120.4	C13—C14—H14	119.3
C3—C4—H4	120.4	C15—C14—H14	119.3
C4—C5—C6	120.48 (14)	C16—C15—C14	117.50 (14)
C4—C5—H5	119.8	C16—C15—C18	120.80 (16)
C6—C5—H5	119.8	C14—C15—C18	121.69 (15)
C7—C6—C5	120.58 (13)	C17—C16—C15	121.93 (15)
C7—C6—H6	119.7	C17—C16—H16	119.0
C5—C6—H6	119.7	C15—C16—H16	119.0
O2—C7—C6	123.63 (12)	C16—C17—C12	120.67 (14)
O2—C7—C2	116.70 (11)	C16—C17—H17	119.7
C6—C7—C2	119.66 (12)	C12—C17—H17	119.7
O2—C8—C9	108.34 (11)	C15—C18—H18A	109.5
O2—C8—H8A	110.0	C15—C18—H18B	109.5
C9—C8—H8A	110.0	H18A—C18—H18B	109.5
O2—C8—H8B	110.0	C15—C18—H18C	109.5
C9—C8—H8B	110.0	H18A—C18—H18C	109.5
H8A—C8—H8B	108.4	H18B—C18—H18C	109.5
C11—C9—C10	123.51 (12)	C1—N1—O1	111.61 (12)
C11—C9—C8	121.38 (13)	N1—O1—H1A	109.5
C10—C9—C8	115.02 (12)	C7—O2—C8	116.51 (10)
N2—C10—C9	176.93 (17)

N1—C1—C2—C3	165.75 (16)	C8—C9—C11—C12	177.74 (13)
N1—C1—C2—C7	−13.2 (3)	C9—C11—C12—C13	−174.78 (14)
C7—C2—C3—C4	1.3 (2)	C9—C11—C12—C17	5.4 (2)
C1—C2—C3—C4	−177.81 (15)	C17—C12—C13—C14	0.5 (2)
C2—C3—C4—C5	1.6 (2)	C11—C12—C13—C14	−179.33 (12)
C3—C4—C5—C6	−2.0 (2)	C12—C13—C14—C15	−0.4 (2)
C4—C5—C6—C7	−0.5 (2)	C13—C14—C15—C16	0.3 (2)
C5—C6—C7—O2	−175.94 (13)	C13—C14—C15—C18	179.17 (14)
C5—C6—C7—C2	3.5 (2)	C14—C15—C16—C17	−0.2 (2)
C3—C2—C7—O2	175.69 (12)	C18—C15—C16—C17	−179.07 (16)
C1—C2—C7—O2	−5.3 (2)	C15—C16—C17—C12	0.2 (3)
C3—C2—C7—C6	−3.8 (2)	C13—C12—C17—C16	−0.4 (2)
C1—C2—C7—C6	175.23 (14)	C11—C12—C17—C16	179.43 (15)
O2—C8—C9—C11	108.86 (14)	C2—C1—N1—O1	−176.87 (15)
O2—C8—C9—C10	−74.60 (16)	C6—C7—O2—C8	8.7 (2)
C11—C9—C10—N2	156 (3)	C2—C7—O2—C8	−170.73 (12)
C8—C9—C10—N2	−21 (3)	C9—C8—O2—C7	162.41 (12)
C10—C9—C11—C12	1.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1ⁱ	0.82	2.10	2.795 (2)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1ⁱ	0.82	2.10	2.795 (2)	143

Symmetry code: (i) .

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