Literature DB >> 21203301

Methyl 2-[(E)-(4-nitro-phen-yl)hydrazono]-3-oxobutyrate.

Yong-Hong Liu, Gui-You Sun, Jian-Feng Liu, Jun Ye, Xiao-Lan Liu.

Abstract

The mol-ecule of the title compound, C(11)H(11)N(3)O(5), exists as the E isomer as it is stabilized by an intra-molecular hydrogen bond. Except for the methyl H atoms, all atoms lie in special positions on a mirror plane and form a large conjugated system; the methyl H atoms are disordered about the mirror plane. In the crystalline state, bifurcated intra- and inter-molecular N-H⋯O hydrogen bonds and four inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into large perfectly planar sheets. Along the c axis, the N-N bond center approaches the phenyl-ring centroids of its neighbouring mol-ecules above and below to give π-π overlap (at a distance of ca 3.57 Å), thus fusing the mol-ecules into a three-dimensional framework.

Entities: Chemical Disease Species

Year: 2008 PMID： 21203301 PMCID： PMC2962099 DOI： 10.1107/S160053680802312X

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

Related literature

For related literature, see: Bernstein et al. (1995 ▶); Lewis et al. (1999 ▶); Liu et al. (2007 ▶, 2008 ▶); Mague et al. (1997 ▶); Mahy et al. (1993 ▶); Serbutoviez et al. (1995 ▶); Thami et al. (1992 ▶); Wang et al. (2005 ▶).

Experimental

Crystal data

C11H11N3O5 M = 265.2 Orthorhombic, a = 12.880 (3) Å b = 14.299 (3) Å c = 6.6328 (14) Å V = 1221.6 (5) Å3 Z = 4 Mo Kα radiation μ = 0.12 mm−1 T = 296 (2) K 0.30 × 0.30 × 0.20 mm

Data collection

Bruker SMART 1000 CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.966, T max = 0.977 10245 measured reflections 1546 independent reflections 968 reflections with I > 2σ(I) R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.042 wR(F 2) = 0.121 S = 1.03 1546 reflections 118 parameters H-atom parameters constrained Δρmax = 0.20 e Å−3 Δρmin = −0.13 e Å−3 Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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, 2003 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680802312X/cs2083sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S160053680802312X/cs2083Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₁H₁₁N₃O₅	D_x = 1.442 Mg m⁻³
M_r = 265.2	Melting point: 400 K
Orthorhombic, Pbcm	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2c 2b	Cell parameters from 1996 reflections
a = 12.880 (3) Å	θ = 2.8–25.4º
b = 14.299 (3) Å	µ = 0.12 mm⁻¹
c = 6.6328 (14) Å	T = 296 (2) K
V = 1221.6 (5) Å³	Block, yellow
Z = 4	0.30 × 0.30 × 0.20 mm
F₀₀₀ = 552

Bruker SMART 1000 CCD diffractometer	1546 independent reflections
Radiation source: fine-focus sealed tube	968 reflections with I > 2σ(I)
Monochromator: graphite	R_int = 0.041
T = 296(2) K	θ_max = 27.6º
Thin–slice ω scans	θ_min = 1.6º
Absorption correction: multi-scan(SADABS; Bruker, 2002)	h = −16→16
T_min = 0.966, T_max = 0.977	k = −17→18
10245 measured reflections	l = −8→8

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.042	w = 1/[σ²(F_o²) + (0.0497P)² + 0.2977P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.121	(Δ/σ)_max < 0.001
S = 1.03	Δρ_max = 0.20 e Å⁻³
1546 reflections	Δρ_min = −0.13 e Å⁻³
118 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0036 (9)
Secondary atom site location: difference Fourier map

	x	y	z	U_iso*/U_eq	Occ. (<1)
O4	0.68298 (15)	0.51128 (12)	0.2500	0.0726 (6)
O3	1.00596 (16)	0.52888 (14)	0.2500	0.0896 (8)
O1	0.68240 (17)	−0.10594 (13)	0.2500	0.0887 (8)
O2	0.52310 (17)	−0.06963 (13)	0.2500	0.1081 (10)
N3	0.61352 (18)	−0.04820 (14)	0.2500	0.0582 (6)
N1	0.72021 (14)	0.33126 (12)	0.2500	0.0422 (5)
H1	0.6721	0.3730	0.2500	0.051*
N2	0.81817 (14)	0.35582 (13)	0.2500	0.0435 (5)
C10	0.7757 (2)	0.52229 (16)	0.2500	0.0489 (6)
C6	0.69506 (16)	0.23623 (15)	0.2500	0.0379 (5)
C8	0.9648 (2)	0.45339 (18)	0.2500	0.0597 (7)
C5	0.59053 (17)	0.21060 (14)	0.2500	0.0436 (6)
H5	0.5392	0.2563	0.2500	0.052*
C2	0.74469 (18)	0.07505 (15)	0.2500	0.0447 (6)
H2	0.7957	0.0290	0.2500	0.054*
C4	0.56352 (18)	0.11723 (15)	0.2500	0.0475 (6)
H4	0.4941	0.0993	0.2500	0.057*
O5	0.81917 (15)	0.60575 (12)	0.2500	0.0768 (7)
C3	0.64146 (18)	0.05094 (15)	0.2500	0.0423 (5)
C1	0.77167 (17)	0.16807 (15)	0.2500	0.0431 (6)
H1A	0.8413	0.1853	0.2500	0.052*
C9	0.84922 (18)	0.44293 (16)	0.2500	0.0453 (6)
C7	1.0288 (2)	0.3663 (2)	0.2500	0.0906 (12)
H7A	1.0318	0.3412	0.1158	0.136*	0.50
H7B	0.9980	0.3211	0.3387	0.136*	0.50
H7C	1.0978	0.3806	0.2954	0.136*	0.50
C11	0.7477 (3)	0.68338 (19)	0.2500	0.0908 (11)
H11A	0.7153	0.6882	0.1201	0.136*	0.50
H11B	0.7847	0.7401	0.2788	0.136*	0.50
H11C	0.6955	0.6735	0.3511	0.136*	0.50

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O4	0.0474 (12)	0.0424 (10)	0.1281 (19)	−0.0013 (8)	0.000	0.000
O3	0.0517 (12)	0.0553 (13)	0.162 (2)	−0.0184 (10)	0.000	0.000
O1	0.0783 (14)	0.0355 (10)	0.152 (2)	0.0124 (10)	0.000	0.000
O2	0.0591 (13)	0.0402 (11)	0.225 (3)	−0.0140 (10)	0.000	0.000
N3	0.0587 (14)	0.0335 (11)	0.0824 (16)	−0.0003 (11)	0.000	0.000
N1	0.0398 (10)	0.0318 (10)	0.0551 (12)	−0.0030 (8)	0.000	0.000
N2	0.0430 (11)	0.0392 (10)	0.0482 (12)	−0.0067 (9)	0.000	0.000
C10	0.0524 (16)	0.0355 (13)	0.0588 (16)	−0.0074 (11)	0.000	0.000
C6	0.0426 (12)	0.0333 (11)	0.0377 (12)	−0.0018 (10)	0.000	0.000
C8	0.0493 (15)	0.0478 (15)	0.0821 (19)	−0.0102 (13)	0.000	0.000
C5	0.0417 (12)	0.0317 (12)	0.0575 (14)	0.0039 (9)	0.000	0.000
C2	0.0434 (13)	0.0358 (12)	0.0547 (14)	0.0065 (10)	0.000	0.000
C4	0.0392 (12)	0.0369 (12)	0.0664 (16)	−0.0023 (10)	0.000	0.000
O5	0.0622 (12)	0.0348 (10)	0.1333 (19)	−0.0092 (9)	0.000	0.000
C3	0.0456 (13)	0.0283 (11)	0.0530 (14)	0.0000 (10)	0.000	0.000
C1	0.0381 (12)	0.0404 (13)	0.0507 (14)	−0.0020 (10)	0.000	0.000
C9	0.0460 (13)	0.0360 (12)	0.0537 (14)	−0.0081 (10)	0.000	0.000
C7	0.0511 (17)	0.0568 (17)	0.164 (4)	−0.0011 (14)	0.000	0.000
C11	0.088 (2)	0.0336 (14)	0.150 (3)	−0.0002 (16)	0.000	0.000

O4—C10	1.204 (3)	C5—C4	1.380 (3)
O3—C8	1.203 (3)	C5—H5	0.9300
O1—N3	1.212 (3)	C2—C3	1.374 (3)
O2—N3	1.204 (3)	C2—C1	1.375 (3)
N3—C3	1.463 (3)	C2—H2	0.9300
N1—N2	1.310 (2)	C4—C3	1.381 (3)
N1—C6	1.397 (3)	C4—H4	0.9300
N1—H1	0.8600	O5—C11	1.442 (3)
N2—C9	1.308 (3)	C1—H1A	0.9300
C10—O5	1.318 (3)	C7—H7A	0.9600
C10—C9	1.478 (3)	C7—H7B	0.9600
C6—C1	1.387 (3)	C7—H7C	0.9600
C6—C5	1.395 (3)	C11—H11A	0.9600
C8—C7	1.494 (4)	C11—H11B	0.9600
C8—C9	1.496 (3)	C11—H11C	0.9600

O2—N3—O1	122.3 (2)	C3—C4—H4	120.6
O2—N3—C3	119.0 (2)	C10—O5—C11	115.2 (2)
O1—N3—C3	118.7 (2)	C2—C3—C4	122.1 (2)
N2—N1—C6	118.96 (18)	C2—C3—N3	118.8 (2)
N2—N1—H1	120.5	C4—C3—N3	119.1 (2)
C6—N1—H1	120.5	C2—C1—C6	120.0 (2)
C9—N2—N1	123.4 (2)	C2—C1—H1A	120.0
O4—C10—O5	122.7 (2)	C6—C1—H1A	120.0
O4—C10—C9	122.3 (2)	N2—C9—C10	122.4 (2)
O5—C10—C9	115.0 (2)	N2—C9—C8	113.5 (2)
C1—C6—C5	120.1 (2)	C10—C9—C8	124.1 (2)
C1—C6—N1	121.24 (19)	C8—C7—H7A	109.5
C5—C6—N1	118.64 (19)	C8—C7—H7B	109.5
O3—C8—C7	120.3 (2)	H7A—C7—H7B	109.5
O3—C8—C9	121.9 (2)	C8—C7—H7C	109.5
C7—C8—C9	117.8 (2)	H7A—C7—H7C	109.5
C4—C5—C6	119.8 (2)	H7B—C7—H7C	109.5
C4—C5—H5	120.1	O5—C11—H11A	109.5
C6—C5—H5	120.1	O5—C11—H11B	109.5
C3—C2—C1	119.2 (2)	H11A—C11—H11B	109.5
C3—C2—H2	120.4	O5—C11—H11C	109.5
C1—C2—H2	120.4	H11A—C11—H11C	109.5
C5—C4—C3	118.8 (2)	H11B—C11—H11C	109.5
C5—C4—H4	120.6

C6—N1—N2—C9	180.0	O1—N3—C3—C4	180.0
N2—N1—C6—C1	0.0	C3—C2—C1—C6	0.0
N2—N1—C6—C5	180.0	C5—C6—C1—C2	0.0
C1—C6—C5—C4	0.0	N1—C6—C1—C2	180.0
N1—C6—C5—C4	180.0	N1—N2—C9—C10	0.0
C6—C5—C4—C3	0.0	N1—N2—C9—C8	180.0
O4—C10—O5—C11	0.0	O4—C10—C9—N2	0.0
C9—C10—O5—C11	180.0	O5—C10—C9—N2	180.0
C1—C2—C3—C4	0.0	O4—C10—C9—C8	180.0
C1—C2—C3—N3	180.0	O5—C10—C9—C8	0.0
C5—C4—C3—C2	0.0	O3—C8—C9—N2	180.0
C5—C4—C3—N3	180.0	C7—C8—C9—N2	0.0
O2—N3—C3—C2	180.0	O3—C8—C9—C10	0.0
O1—N3—C3—C2	0.0	C7—C8—C9—C10	180.0
O2—N3—C3—C4	0.0

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.86	1.98	2.618 (3)	130
C2—H2···O3ⁱ	0.93	2.55	3.279 (3)	135
C11—H11B···O1ⁱⁱ	0.96	2.57	3.128 (3)	117
N1—H1···O2ⁱⁱⁱ	0.86	2.64	3.439 (3)	154
C5—H5···O2ⁱⁱⁱ	0.93	2.62	3.467 (4)	153
C4ⁱⁱⁱ—H4ⁱⁱⁱ···O4	0.93	2.61	3.518 (3)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4	0.86	1.98	2.618 (3)	130
C2—H2⋯O3ⁱ	0.93	2.55	3.279 (3)	135
C11—H11B⋯O1ⁱⁱ	0.96	2.57	3.128 (3)	117
N1—H1⋯O2ⁱⁱⁱ	0.86	2.64	3.439 (3)	154
C5—H5⋯O2ⁱⁱⁱ	0.93	2.62	3.467 (4)	153
C4ⁱⁱⁱ—H4ⁱⁱⁱ⋯O4	0.93	2.61	3.518 (3)	167

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

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