Literature DB >> 22412510

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

Suresh Govindan, Sabari Vijayakumar, Srinivasan Jayakumar, Bakthadoss Mannickam, Aravindhan Sanmargam.

Abstract

In the title compound, C(17)H(14)N(2)O(2), the n class="Chemical">hy-droxy-ethanimine group adopts an anti-periplanar conformation. In the crystal, mol-ecules are linked by O-H⋯N hydrogen bonds, forming zigzag chains running along the c axis.

Entities: Chemical Disease Species

Year: 2012 PMID： 22412510 PMCID： PMC3297320 DOI： 10.1107/S1600536812003923

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

C17H14N2O2 M = 278.30 Monoclinic, a = 15.8867 (5) Å b = 6.2381 (2) Å c = 15.1874 (4) Å β = 107.199 (2)° V = 1437.81 (7) Å3 Z = 4 Mo Kα radiation μ = 0.09 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 19516 measured reflections 4490 independent reflections 2774 reflections with I > 2σ(I) R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.049 wR(F 2) = 0.131 S = 0.99 4490 reflections 191 parameters H-atom parameters constrained Δρmax = 0.19 e Å−3 Δρmin = −0.21 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/S1600536812003923/bt5765sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003923/bt5765Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812003923/bt5765Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₇H₁₄N₂O₂	F(000) = 584
M_r = 278.30	D_x = 1.286 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8725 reflections
a = 15.8867 (5) Å	θ = 2.8–29.1°
b = 6.2381 (2) Å	µ = 0.09 mm⁻¹
c = 15.1874 (4) Å	T = 293 K
β = 107.199 (2)°	Monoclinic, colourless
V = 1437.81 (7) Å³	0.2 × 0.2 × 0.2 mm
Z = 4

Oxford Diffraction Xcalibur-S diffractometer	4490 independent reflections
Radiation source: fine-focus sealed tube	2774 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 15.9948 pixels mm^-1	θ_max = 31.4°, θ_min = 2.7°
ω scans	h = −20→23
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −9→9
T_min = 0.980, T_max = 0.990	l = −22→22
19516 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0521P)² + 0.226P] where P = (F_o² + 2F_c²)/3
4490 reflections	(Δ/σ)_max < 0.001
191 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

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	0.30906 (9)	0.0194 (2)	0.29768 (9)	0.0471 (3)
H1	0.2662	0.0231	0.2407	0.057*
C2	0.37843 (8)	0.1812 (2)	0.31995 (8)	0.0405 (3)
C3	0.44575 (9)	0.1763 (2)	0.40269 (9)	0.0500 (3)
H3	0.4456	0.0697	0.4455	0.060*
C4	0.51256 (9)	0.3247 (2)	0.42297 (9)	0.0525 (3)
H4	0.5574	0.3176	0.4784	0.063*
C5	0.51234 (9)	0.4837 (2)	0.36050 (10)	0.0542 (4)
H5	0.5574	0.5849	0.3740	0.065*
C6	0.44610 (9)	0.4954 (2)	0.27781 (9)	0.0488 (3)
H6	0.4464	0.6041	0.2360	0.059*
C7	0.37943 (8)	0.3449 (2)	0.25758 (8)	0.0399 (3)
C8	0.30879 (9)	0.5024 (2)	0.11052 (9)	0.0474 (3)
H8A	0.3612	0.4952	0.0904	0.057*
H8B	0.3058	0.6435	0.1363	0.057*
C9	0.22813 (8)	0.4609 (2)	0.03129 (8)	0.0411 (3)
C10	0.22894 (9)	0.2607 (2)	−0.01427 (9)	0.0486 (3)
C11	0.16197 (9)	0.6014 (2)	0.00727 (8)	0.0444 (3)
H11	0.1718	0.7251	0.0431	0.053*
C12	0.07740 (9)	0.5990 (2)	−0.06398 (8)	0.0435 (3)
C13	0.04331 (10)	0.4260 (2)	−0.12169 (10)	0.0577 (4)
H13	0.0768	0.3021	−0.1177	0.069*
C14	−0.03912 (10)	0.4363 (3)	−0.18424 (10)	0.0629 (4)
H14	−0.0607	0.3196	−0.2223	0.075*
C15	−0.08983 (10)	0.6164 (3)	−0.19123 (11)	0.0633 (4)
H15	−0.1460	0.6212	−0.2330	0.076*
C16	−0.05728 (11)	0.7892 (3)	−0.13634 (12)	0.0694 (5)
H16	−0.0911	0.9128	−0.1414	0.083*
C17	0.02527 (10)	0.7807 (2)	−0.07360 (10)	0.0577 (4)
H17	0.0466	0.8996	−0.0368	0.069*
N1	0.30657 (8)	−0.12586 (19)	0.35497 (8)	0.0527 (3)
N2	0.23413 (9)	0.0992 (2)	−0.04726 (10)	0.0728 (4)
O1	0.23639 (8)	−0.26430 (19)	0.31926 (8)	0.0716 (3)
H1A	0.2369	−0.3587	0.3570	0.107*
O2	0.31108 (6)	0.34087 (15)	0.17729 (6)	0.0487 (2)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0432 (7)	0.0502 (8)	0.0433 (7)	0.0001 (6)	0.0055 (6)	0.0077 (6)
C2	0.0369 (6)	0.0437 (7)	0.0396 (6)	0.0029 (5)	0.0093 (5)	0.0023 (5)
C3	0.0488 (8)	0.0581 (8)	0.0397 (7)	0.0044 (7)	0.0079 (6)	0.0084 (6)
C4	0.0455 (8)	0.0654 (9)	0.0387 (7)	0.0008 (7)	0.0004 (6)	−0.0043 (6)
C5	0.0488 (8)	0.0567 (9)	0.0514 (8)	−0.0101 (7)	0.0061 (6)	−0.0076 (7)
C6	0.0479 (8)	0.0474 (8)	0.0470 (7)	−0.0046 (6)	0.0075 (6)	0.0040 (6)
C7	0.0359 (6)	0.0441 (7)	0.0372 (6)	0.0032 (5)	0.0070 (5)	0.0013 (5)
C8	0.0481 (8)	0.0434 (7)	0.0456 (7)	−0.0020 (6)	0.0060 (6)	0.0092 (6)
C9	0.0460 (7)	0.0386 (6)	0.0367 (6)	−0.0009 (5)	0.0090 (5)	0.0048 (5)
C10	0.0443 (8)	0.0476 (8)	0.0497 (7)	0.0045 (6)	0.0076 (6)	0.0034 (6)
C11	0.0524 (8)	0.0397 (7)	0.0387 (6)	0.0005 (6)	0.0096 (6)	−0.0009 (5)
C12	0.0453 (7)	0.0462 (7)	0.0377 (6)	0.0033 (6)	0.0104 (5)	0.0028 (5)
C13	0.0551 (9)	0.0542 (9)	0.0547 (8)	0.0079 (7)	0.0023 (7)	−0.0070 (7)
C14	0.0565 (10)	0.0695 (10)	0.0541 (9)	−0.0032 (8)	0.0030 (7)	−0.0095 (7)
C15	0.0449 (8)	0.0833 (12)	0.0551 (9)	0.0031 (8)	0.0048 (7)	0.0054 (8)
C16	0.0536 (10)	0.0700 (11)	0.0773 (11)	0.0192 (8)	0.0080 (8)	0.0012 (9)
C17	0.0551 (9)	0.0527 (9)	0.0602 (9)	0.0091 (7)	0.0093 (7)	−0.0048 (7)
N1	0.0521 (7)	0.0517 (7)	0.0522 (7)	−0.0081 (5)	0.0119 (5)	0.0032 (5)
N2	0.0731 (10)	0.0553 (8)	0.0837 (10)	0.0116 (7)	0.0136 (8)	−0.0131 (7)
O1	0.0701 (8)	0.0631 (7)	0.0727 (7)	−0.0239 (6)	0.0074 (6)	0.0106 (6)
O2	0.0427 (5)	0.0525 (5)	0.0421 (5)	−0.0062 (4)	−0.0009 (4)	0.0133 (4)

C1—N1	1.2649 (16)	C9—C11	1.3339 (18)
C1—C2	1.4583 (18)	C9—C10	1.4296 (19)
C1—H1	0.9300	C10—N2	1.1392 (17)
C2—C3	1.3889 (18)	C11—C12	1.4548 (18)
C2—C7	1.3962 (17)	C11—H11	0.9300
C3—C4	1.373 (2)	C12—C17	1.3857 (19)
C3—H3	0.9300	C12—C13	1.3951 (19)
C4—C5	1.372 (2)	C13—C14	1.373 (2)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.3814 (19)	C14—C15	1.368 (2)
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.3804 (18)	C15—C16	1.367 (2)
C6—H6	0.9300	C15—H15	0.9300
C7—O2	1.3725 (14)	C16—C17	1.375 (2)
C8—O2	1.4225 (14)	C16—H16	0.9300
C8—C9	1.4983 (18)	C17—H17	0.9300
C8—H8A	0.9700	N1—O1	1.3876 (15)
C8—H8B	0.9700	O1—H1A	0.8200

N1—C1—C2	120.76 (12)	C11—C9—C8	121.58 (12)
N1—C1—H1	119.6	C10—C9—C8	114.31 (11)
C2—C1—H1	119.6	N2—C10—C9	176.18 (16)
C3—C2—C7	118.02 (12)	C9—C11—C12	132.56 (12)
C3—C2—C1	121.43 (12)	C9—C11—H11	113.7
C7—C2—C1	120.55 (11)	C12—C11—H11	113.7
C4—C3—C2	121.70 (13)	C17—C12—C13	117.24 (13)
C4—C3—H3	119.2	C17—C12—C11	117.49 (12)
C2—C3—H3	119.2	C13—C12—C11	125.23 (12)
C5—C4—C3	119.26 (12)	C14—C13—C12	120.79 (14)
C5—C4—H4	120.4	C14—C13—H13	119.6
C3—C4—H4	120.4	C12—C13—H13	119.6
C4—C5—C6	120.82 (13)	C15—C14—C13	120.76 (15)
C4—C5—H5	119.6	C15—C14—H14	119.6
C6—C5—H5	119.6	C13—C14—H14	119.6
C7—C6—C5	119.64 (12)	C16—C15—C14	119.48 (14)
C7—C6—H6	120.2	C16—C15—H15	120.3
C5—C6—H6	120.2	C14—C15—H15	120.3
O2—C7—C6	124.30 (11)	C15—C16—C17	120.22 (15)
O2—C7—C2	115.14 (11)	C15—C16—H16	119.9
C6—C7—C2	120.56 (11)	C17—C16—H16	119.9
O2—C8—C9	106.60 (10)	C16—C17—C12	121.48 (15)
O2—C8—H8A	110.4	C16—C17—H17	119.3
C9—C8—H8A	110.4	C12—C17—H17	119.3
O2—C8—H8B	110.4	C1—N1—O1	111.22 (11)
C9—C8—H8B	110.4	N1—O1—H1A	109.5
H8A—C8—H8B	108.6	C7—O2—C8	117.86 (9)
C11—C9—C10	124.11 (12)

N1—C1—C2—C3	2.7 (2)	C8—C9—C11—C12	−178.61 (12)
N1—C1—C2—C7	−178.10 (13)	C9—C11—C12—C17	−176.32 (13)
C7—C2—C3—C4	−1.05 (19)	C9—C11—C12—C13	5.7 (2)
C1—C2—C3—C4	178.19 (12)	C17—C12—C13—C14	−0.9 (2)
C2—C3—C4—C5	0.8 (2)	C11—C12—C13—C14	177.09 (14)
C3—C4—C5—C6	−0.2 (2)	C12—C13—C14—C15	−0.2 (2)
C4—C5—C6—C7	−0.2 (2)	C13—C14—C15—C16	1.1 (3)
C5—C6—C7—O2	−179.43 (12)	C14—C15—C16—C17	−1.0 (3)
C5—C6—C7—C2	0.0 (2)	C15—C16—C17—C12	−0.1 (3)
C3—C2—C7—O2	−179.90 (11)	C13—C12—C17—C16	1.1 (2)
C1—C2—C7—O2	0.86 (16)	C11—C12—C17—C16	−177.09 (14)
C3—C2—C7—C6	0.63 (18)	C2—C1—N1—O1	−178.97 (12)
C1—C2—C7—C6	−178.62 (12)	C6—C7—O2—C8	0.00 (18)
O2—C8—C9—C11	116.39 (13)	C2—C7—O2—C8	−179.45 (11)
O2—C8—C9—C10	−63.22 (14)	C9—C8—O2—C7	−179.66 (10)
C10—C9—C11—C12	1.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N2ⁱ	0.82	2.10	2.9187 (17)	178

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N2ⁱ	0.82	2.10	2.9187 (17)	178

Symmetry code: (i) .

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