Literature DB >> 22412509

3-Meth-oxy-3-oxopropanaminium chloride.

Tobias Gruber, Christopher J Schofield, Amber L Thompson.

Abstract

In the title compound, C(4)H(10)NO(2) (+)·Cl(-), the central ethyl-ene bond of the cation adopts a gauche conformation. The three H atoms of the -NH(3) (+) group are engaged in strong and highly directional inter-molecular N-H⋯Cl hydrogen bonds, which result in a tape-like arrangement along [010] of the respective ion pairs. In addition, weak inter-molecular C-H⋯Cl and C-H⋯O inter-actions are present.

Entities: Chemical Disease Species

Year: 2012 PMID： 22412509 PMCID： PMC3297319 DOI： 10.1107/S1600536812003297

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

Related literature

For the synthesis of the title compound, see: Hansen (1963 ▶). For related structures, see: Akkerman et al. (2003 ▶); Robinson et al. (2004 ▶); Vilela et al. (2009 ▶); Tarafdar & Swamy (2010 ▶); Gossage et al. (2010 ▶); He et al. (2010 ▶). For information on the gauche effect, see: Amos et al. (1992 ▶). For details of the H-atom treatment, see: Cooper et al. (2010 ▶). For the weighting scheme used in the refinement, see: Watkin (1994 ▶); Prince (1982 ▶).

Experimental

Crystal data

C4H10NO2 +·Cl− M = 139.58 Monoclinic, a = 9.8469 (2) Å b = 5.3263 (1) Å c = 13.2804 (2) Å β = 99.4638 (10)° V = 687.04 (2) Å3 Z = 4 Mo Kα radiation μ = 0.47 mm−1 T = 150 K 0.28 × 0.13 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer Absorption correction: multi-scan DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶) T min = 0.94, T max = 0.96 14336 measured reflections 1563 independent reflections 1413 reflections with I > 2σ(I) R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.032 wR(F 2) = 0.080 S = 0.93 1563 reflections 73 parameters H-atom parameters constrained Δρmax = 0.25 e Å−3 Δρmin = −0.28 e Å−3 Data collection: COLLECT (Nonius, 2001 ▶).; cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: CAMERON (Watkin et al., 1996 ▶); software used to prepare material for publication: CRYSTALS and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812003297/lh5384sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003297/lh5384Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812003297/lh5384Isup3.cdx Supplementary material file. DOI: 10.1107/S1600536812003297/lh5384Isup4.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₄H₁₀NO₂⁺·Cl⁻	F(000) = 296
M_r = 139.58	D_x = 1.349 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1729 reflections
a = 9.8469 (2) Å	θ = 5–27°
b = 5.3263 (1) Å	µ = 0.47 mm⁻¹
c = 13.2804 (2) Å	T = 150 K
β = 99.4638 (10)°	Block, clear_pale_colourless
V = 687.04 (2) Å³	0.28 × 0.13 × 0.08 mm
Z = 4

Nonius KappaCCD diffractometer	1413 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
ω scans	θ_max = 27.5°, θ_min = 5.2°
Absorption correction: multi-scan DENZO/SCALEPACK (Otwinowski & Minor, 1997)	h = −12→12
T_min = 0.94, T_max = 0.96	k = −6→6
14336 measured reflections	l = −17→17
1563 independent reflections

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.080	Method, part 1, Chebychev polynomial, (Watkin, 1994; Prince, 1982) [weight] = 1.0/[A₀T₀(x) + A₁T₁(x) ··· + A_n-1]T_n-1(x)] where A_i are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] [1-(deltaF/6*sigmaF)²]² A_i are: 37.6 62.5 38.0 16.9 4.31
S = 0.93	(Δ/σ)_max = 0.001
1563 reflections	Δρ_max = 0.25 e Å⁻³
73 parameters	Δρ_min = −0.28 e Å⁻³
0 restraints

	x	y	z	U_iso*/U_eq
Cl1	0.92411 (3)	0.72604 (6)	0.59816 (2)	0.0244
O2	0.72167 (10)	1.11170 (19)	0.75243 (7)	0.0236
C3	0.62577 (14)	1.0662 (3)	0.66935 (11)	0.0241
O4	0.53381 (11)	0.9165 (2)	0.66871 (8)	0.0335
C5	0.64993 (16)	1.2257 (3)	0.58178 (12)	0.0307
C6	0.70489 (15)	0.9789 (3)	0.84455 (10)	0.0257
C7	0.76188 (14)	0.7166 (3)	0.84666 (10)	0.0240
N8	0.91018 (12)	0.7208 (2)	0.83652 (9)	0.0235
H51	0.7403	1.1944	0.5697	0.0451*
H52	0.6422	1.3972	0.6003	0.0448*
H53	0.5842	1.1883	0.5224	0.0448*
H61	0.7569	1.0756	0.8995	0.0291*
H62	0.6067	0.9749	0.8523	0.0288*
H71	0.7136	0.6156	0.7909	0.0287*
H72	0.7551	0.6399	0.9112	0.0286*
H81	0.9506	0.5763	0.8594	0.0342*
H82	0.9161	0.7420	0.7690	0.0341*
H83	0.9517	0.8494	0.8726	0.0346*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.02820 (19)	0.02258 (18)	0.02136 (18)	−0.00083 (12)	0.00108 (12)	−0.00105 (12)
O2	0.0248 (5)	0.0223 (5)	0.0222 (5)	−0.0002 (4)	−0.0009 (4)	0.0002 (4)
C3	0.0238 (6)	0.0228 (6)	0.0243 (6)	0.0016 (5)	−0.0005 (5)	−0.0012 (5)
O4	0.0303 (5)	0.0348 (6)	0.0329 (6)	−0.0080 (5)	−0.0025 (4)	0.0039 (5)
C5	0.0332 (8)	0.0305 (8)	0.0268 (7)	−0.0027 (6)	0.0000 (6)	0.0047 (6)
C6	0.0292 (7)	0.0278 (7)	0.0200 (6)	0.0021 (6)	0.0041 (5)	−0.0010 (5)
C7	0.0268 (7)	0.0229 (6)	0.0215 (6)	−0.0016 (5)	0.0017 (5)	0.0021 (5)
N8	0.0287 (6)	0.0202 (5)	0.0208 (5)	0.0032 (4)	0.0015 (4)	0.0012 (4)

O2—C3	1.3509 (16)	C6—H61	0.968
O2—C6	1.4459 (17)	C6—H62	0.989
C3—O4	1.2057 (18)	C7—N8	1.4886 (18)
C3—C5	1.490 (2)	C7—H71	0.973
C5—H51	0.945	C7—H72	0.961
C5—H52	0.952	N8—H81	0.896
C5—H53	0.955	N8—H82	0.915
C6—C7	1.504 (2)	N8—H83	0.895

C3—O2—C6	116.20 (11)	C7—C6—H62	110.2
O2—C3—O4	123.21 (13)	H61—C6—H62	109.8
O2—C3—C5	110.81 (12)	C6—C7—N8	110.65 (11)
O4—C3—C5	125.98 (13)	C6—C7—H71	111.4
C3—C5—H51	107.9	N8—C7—H71	107.7
C3—C5—H52	108.4	C6—C7—H72	109.3
H51—C5—H52	109.3	N8—C7—H72	107.5
C3—C5—H53	110.6	H71—C7—H72	110.2
H51—C5—H53	110.7	C7—N8—H81	110.1
H52—C5—H53	109.9	C7—N8—H82	108.2
O2—C6—C7	112.08 (11)	H81—N8—H82	110.0
O2—C6—H61	104.9	C7—N8—H83	109.3
C7—C6—H61	109.3	H81—N8—H83	109.7
O2—C6—H62	110.3	H82—N8—H83	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N8—H81···Cl1ⁱ	0.90	2.26	3.1456 (12)	171 (1)
N8—H82···Cl1	0.92	2.29	3.1910 (12)	171 (1)
N8—H83···Cl1ⁱⁱ	0.90	2.35	3.1923 (12)	157 (1)
C5—H53···O4ⁱⁱⁱ	0.96	2.67	3.5965 (18)	163 (1)
C7—H72···Cl1^iv	0.96	2.84	3.4708 (14)	124 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N8—H81⋯Cl1ⁱ	0.90	2.26	3.1456 (12)	171 (1)
N8—H82⋯Cl1	0.92	2.29	3.1910 (12)	171 (1)
N8—H83⋯Cl1ⁱⁱ	0.90	2.35	3.1923 (12)	157 (1)
C5—H53⋯O4ⁱⁱⁱ	0.96	2.67	3.5965 (18)	163 (1)
C7—H72⋯Cl1^iv	0.96	2.84	3.4708 (14)	124 (1)

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

4 in total

1. Structure and phase behavior of O-stearoylethanolamine: a combined calorimetric, spectroscopic and X-ray diffraction study.

Authors: Pradip K Tarafdar; Musti J Swamy
Journal: Biochim Biophys Acta Date: 2010-01-28