Literature DB >> 22058943

Ethyl (2E)-2-cyano-3-(1-methyl-1H-pyrrol-2-yl)prop-2-enoate.

Abdullah M Asiri, Abdulrahman O Al-Youbi, Khalid A Alamry, Hassan M Faidallah, Seik Weng Ng, Edward R T Tiekink.

Abstract

The 15 non-H atoms of the title compound, C(11)H(12)N(2)O(2), are approximately coplanar, the r.m.s. deviation being 0.145 Å. The major deviation from coplanarity is seen in a twist between the n class="Chemical">ethene (E configuration) and pyrrole rings [C-C-N-C torsion angle = -8.26 (18)°]. The carbonyl O and cyano N atoms are syn to each other. In the crystal, supra-molecular linear tapes linked by C-H⋯O and C-H⋯N inter-actions are further connected by C-H⋯π(pyrrole) inter-actions.

Entities: Chemical Disease Species

Year: 2011 PMID： 22058943 PMCID： PMC3200670 DOI： 10.1107/S1600536811031941

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

Related literature

For background to the biological activity of 2(1H)pyridone compounds, see: Aly et al. (1991 ▶); Al-Saadi et al. (2005 ▶); n class="Chemical">Rostom et al. (2011 ▶).

Experimental

Crystal data

C11H12N2O2 M = 204.23 Triclinic, a = 7.6145 (3) Å b = 8.4964 (6) Å c = 9.7023 (6) Å α = 64.898 (7)° β = 89.859 (4)° γ = 71.517 (5)° V = 532.69 (5) Å3 Z = 2 Mo Kα radiation μ = 0.09 mm−1 T = 100 K 0.30 × 0.25 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.955, T max = 1.000 4049 measured reflections 2336 independent reflections 1912 reflections with I > 2σ(I) R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 0.106 S = 1.04 2336 reflections 138 parameters H-atom parameters constrained Δρmax = 0.26 e Å−3 Δρmin = −0.21 e Å−3 Data collection: CrysAlis PRO (Agilent, 2010 ▶); 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 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811031941/hb6354sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031941/hb6354Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₁H₁₂N₂O₂	Z = 2
M_r = 204.23	F(000) = 216
Triclinic, P1	D_x = 1.273 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6145 (3) Å	Cell parameters from 2042 reflections
b = 8.4964 (6) Å	θ = 2.3–29.2°
c = 9.7023 (6) Å	µ = 0.09 mm⁻¹
α = 64.898 (7)°	T = 100 K
β = 89.859 (4)°	Block, yellow
γ = 71.517 (5)°	0.30 × 0.25 × 0.10 mm
V = 532.69 (5) Å³

Agilent SuperNova Dual diffractometer with an Atlas detector	2336 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1912 reflections with I > 2σ(I)
mirror	R_int = 0.030
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.4°
ω scans	h = −8→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −8→11
T_min = 0.955, T_max = 1.000	l = −12→11
4049 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.043P)² + 0.1378P] where P = (F_o² + 2F_c²)/3
2336 reflections	(Δ/σ)_max < 0.001
138 parameters	Δρ_max = 0.26 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
O1	0.76560 (13)	0.39008 (13)	0.75762 (10)	0.0210 (2)
O2	0.94151 (13)	0.24631 (13)	0.62962 (11)	0.0240 (2)
N2	0.31730 (15)	0.98384 (16)	0.40412 (13)	0.0195 (3)
C1	0.7806 (2)	0.2663 (2)	1.02981 (18)	0.0367 (4)
H1A	0.8394	0.1579	1.1287	0.055*
H1B	0.6452	0.2928	1.0165	0.055*
H1C	0.8049	0.3737	1.0280	0.055*
C2	0.8606 (2)	0.22752 (19)	0.90199 (16)	0.0239 (3)
H2A	0.9970	0.2036	0.9128	0.029*
H2B	0.8402	0.1170	0.9045	0.029*
C3	0.82056 (17)	0.37907 (18)	0.63059 (15)	0.0178 (3)
C4	0.71681 (17)	0.54814 (18)	0.48907 (15)	0.0177 (3)
C5	0.77316 (18)	0.54540 (18)	0.34926 (16)	0.0198 (3)
C6	0.57429 (17)	0.68970 (18)	0.49404 (15)	0.0176 (3)
H6	0.5455	0.6706	0.5940	0.021*
C7	0.46245 (17)	0.86137 (18)	0.37221 (15)	0.0185 (3)
C8	0.47051 (19)	0.95100 (19)	0.21554 (16)	0.0225 (3)
H8	0.5559	0.9015	0.1603	0.027*
C9	0.3314 (2)	1.1258 (2)	0.15416 (17)	0.0268 (3)
H9	0.3051	1.2171	0.0499	0.032*
C10	0.23870 (19)	1.14206 (19)	0.27246 (16)	0.0241 (3)
H10	0.1364	1.2471	0.2631	0.029*
C11	0.25065 (19)	0.9441 (2)	0.55193 (16)	0.0230 (3)
H11A	0.1556	1.0568	0.5462	0.034*
H11B	0.3559	0.9013	0.6323	0.034*
H11C	0.1956	0.8473	0.5767	0.034*
N1	0.81855 (17)	0.53952 (17)	0.23809 (14)	0.0273 (3)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0231 (5)	0.0179 (5)	0.0169 (5)	−0.0016 (4)	0.0022 (4)	−0.0073 (4)
O2	0.0218 (5)	0.0215 (5)	0.0278 (6)	−0.0014 (4)	0.0028 (4)	−0.0145 (4)
N2	0.0176 (5)	0.0198 (6)	0.0224 (6)	−0.0041 (5)	0.0011 (4)	−0.0122 (5)
C1	0.0394 (9)	0.0389 (10)	0.0209 (8)	−0.0062 (8)	0.0046 (7)	−0.0089 (7)
C2	0.0269 (7)	0.0183 (7)	0.0187 (7)	−0.0043 (6)	−0.0005 (6)	−0.0038 (6)
C3	0.0163 (6)	0.0193 (7)	0.0206 (7)	−0.0061 (5)	0.0036 (5)	−0.0116 (6)
C4	0.0167 (6)	0.0202 (7)	0.0194 (7)	−0.0076 (5)	0.0035 (5)	−0.0108 (6)
C5	0.0183 (6)	0.0179 (7)	0.0225 (7)	−0.0044 (5)	0.0019 (5)	−0.0098 (6)
C6	0.0169 (6)	0.0211 (7)	0.0190 (7)	−0.0084 (5)	0.0037 (5)	−0.0115 (5)
C7	0.0174 (6)	0.0190 (7)	0.0208 (7)	−0.0054 (5)	0.0019 (5)	−0.0111 (6)
C8	0.0254 (7)	0.0231 (7)	0.0204 (7)	−0.0069 (6)	0.0011 (5)	−0.0120 (6)
C9	0.0305 (8)	0.0234 (8)	0.0213 (7)	−0.0055 (6)	−0.0048 (6)	−0.0082 (6)
C10	0.0211 (7)	0.0194 (7)	0.0282 (8)	−0.0012 (6)	−0.0045 (6)	−0.0115 (6)
C11	0.0199 (7)	0.0251 (8)	0.0283 (8)	−0.0059 (6)	0.0061 (6)	−0.0172 (6)
N1	0.0325 (7)	0.0267 (7)	0.0234 (7)	−0.0074 (6)	0.0076 (5)	−0.0139 (5)

O1—C3	1.3316 (16)	C4—C5	1.4290 (19)
O1—C2	1.4570 (16)	C5—N1	1.1482 (17)
O2—C3	1.2128 (15)	C6—C7	1.4158 (18)
N2—C10	1.3542 (18)	C6—H6	0.9500
N2—C7	1.3938 (17)	C7—C8	1.3933 (19)
N2—C11	1.4568 (18)	C8—C9	1.392 (2)
C1—C2	1.494 (2)	C8—H8	0.9500
C1—H1A	0.9800	C9—C10	1.380 (2)
C1—H1B	0.9800	C9—H9	0.9500
C1—H1C	0.9800	C10—H10	0.9500
C2—H2A	0.9900	C11—H11A	0.9800
C2—H2B	0.9900	C11—H11B	0.9800
C3—C4	1.4783 (18)	C11—H11C	0.9800
C4—C6	1.3594 (18)

C3—O1—C2	115.44 (10)	N1—C5—C4	178.60 (15)
C10—N2—C7	108.92 (11)	C4—C6—C7	129.52 (13)
C10—N2—C11	125.09 (11)	C4—C6—H6	115.2
C7—N2—C11	125.83 (11)	C7—C6—H6	115.2
C2—C1—H1A	109.5	C8—C7—N2	106.74 (11)
C2—C1—H1B	109.5	C8—C7—C6	133.53 (12)
H1A—C1—H1B	109.5	N2—C7—C6	119.56 (12)
C2—C1—H1C	109.5	C9—C8—C7	107.97 (13)
H1A—C1—H1C	109.5	C9—C8—H8	126.0
H1B—C1—H1C	109.5	C7—C8—H8	126.0
O1—C2—C1	107.45 (11)	C10—C9—C8	107.48 (13)
O1—C2—H2A	110.2	C10—C9—H9	126.3
C1—C2—H2A	110.2	C8—C9—H9	126.3
O1—C2—H2B	110.2	N2—C10—C9	108.89 (12)
C1—C2—H2B	110.2	N2—C10—H10	125.6
H2A—C2—H2B	108.5	C9—C10—H10	125.6
O2—C3—O1	124.42 (12)	N2—C11—H11A	109.5
O2—C3—C4	123.32 (12)	N2—C11—H11B	109.5
O1—C3—C4	112.26 (11)	H11A—C11—H11B	109.5
C6—C4—C5	123.65 (12)	N2—C11—H11C	109.5
C6—C4—C3	121.69 (12)	H11A—C11—H11C	109.5
C5—C4—C3	114.60 (11)	H11B—C11—H11C	109.5

C3—O1—C2—C1	179.92 (11)	C10—N2—C7—C6	176.08 (11)
C2—O1—C3—O2	−0.45 (18)	C11—N2—C7—C6	−8.26 (18)
C2—O1—C3—C4	179.47 (10)	C4—C6—C7—C8	−8.2 (2)
O2—C3—C4—C6	175.93 (12)	C4—C6—C7—N2	177.34 (12)
O1—C3—C4—C6	−3.99 (17)	N2—C7—C8—C9	0.03 (15)
O2—C3—C4—C5	−1.38 (18)	C6—C7—C8—C9	−174.98 (14)
O1—C3—C4—C5	178.70 (10)	C7—C8—C9—C10	−0.29 (16)
C5—C4—C6—C7	−4.1 (2)	C7—N2—C10—C9	−0.43 (15)
C3—C4—C6—C7	178.85 (12)	C11—N2—C10—C9	−176.13 (12)
C10—N2—C7—C8	0.24 (14)	C8—C9—C10—N2	0.44 (16)
C11—N2—C7—C8	175.90 (11)

Cg1 is the centroid of the N2,C7—C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11a···O2ⁱ	0.98	2.31	3.241 (2)	158
C9—H9···N1ⁱⁱ	0.95	2.62	3.557 (2)	171
C11—H11b···Cg1ⁱⁱⁱ	0.98	2.69	3.5332 (17)	144

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N2,C7—C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11a⋯O2ⁱ	0.98	2.31	3.241 (2)	158
C9—H9⋯N1ⁱⁱ	0.95	2.62	3.557 (2)	171
C11—H11b⋯Cg1ⁱⁱⁱ	0.98	2.69	3.5332 (17)	144

Symmetry codes: (i) ; (ii) ; (iii) .

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