Diisoprop­yl{2-[2-(2-oxopyrrolidin-1-yl)acetamido]eth­yl}ammonium hydrogen sulfate

Bambagiotti-Alberti, M.; Bartolucci, G.; Bruni, B.; Coran, S.A.; Di Vaira, M.

doi:10.1107/S1600536808015341

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1160

doi:10.1107/S1600536808015341

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Diisopropyl{2-[2-(2-oxopyrrolidin-1-yl)acetamido]ethyl}ammonium hydrogen sulfate

Massimo Bambagiotti-Alberti,^a Gianluca Bartolucci,^a Bruno Bruni,^a Silvia A. Coran ^a and Massimo Di Vaira ^b ^*

^aDipartimento di Scienze Farmaceutiche, Universitá di Firenze, Via U. Schiff 6, I-50019 Sesto Fiorentino, Firenze, Italy, and ^bDipartimento di Chimica, Universitá di Firenze, Via della Lastruccia 3, I-50019 Sesto Fiorentino, Firenze, Italy
^*Correspondence e-mail: massimo.divaira@unifi.it

(Received 12 May 2008; accepted 21 May 2008; online 30 May 2008)

The structure of the title compound, C₁₄H₂₈N₃O₂⁺·HSO₄⁻, a nootropic drug (pramiracetam) investigated for cognition-enhancing properties, is closely similar to that of the previously determined acetonitrile solvate, both structures being characterized by the presence of ribbons of hydrogen-bonded ions. The pyrrolidine ring adopts an envelope conformation.

Related literature

For related literature, see: Claus et al. (1991 ); Gouliaev & Senning (1994 ); Mondadori et al. (1991 ); Pugsley et al. (1983 ). For a related structure, see: Bandoli et al. (1987 ).

Experimental

Crystal data

C₁₄H₂₈N₃O₂⁺·HSO₄⁻
M_r = 367.46
Triclinic, $[P \overline 1]$
a = 6.7834 (3) Å
b = 11.1755 (4) Å
c = 12.9012 (6) Å
α = 72.165 (4)°
β = 89.394 (4)°
γ = 89.509 (3)°
V = 930.95 (7) Å³
Z = 2
Cu Kα radiation
μ = 1.85 mm⁻¹
T = 170 (2) K
0.50 × 0.25 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur PX Ultra CCD diffractometer
Absorption correction: multi-scan (ABSPACK in CrysAlisPro RED; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlisPro CCD and CrysAlisPro RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.762, T_max = 1.000 (expected range = 0.634–0.831)
7656 measured reflections
3356 independent reflections
3253 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.132
S = 1.06
3356 reflections
230 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.57 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3	0.86 (3)	2.10 (3)	2.948 (2)	172 (2)
N3—H3⋯O4ⁱ	0.97 (3)	1.79 (3)	2.764 (2)	175 (2)
O6—H6⋯O1ⁱⁱ	0.90 (4)	1.68 (4)	2.559 (2)	167 (3)
C12—H12⋯O2ⁱⁱⁱ	1.00	2.40	3.362 (3)	162
C13—H131⋯O4^iv	0.98	2.59	3.559 (2)	171
C14—H143⋯O5	0.98	2.56	3.530 (2)	172
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+1, -z+2; (iii) x-1, y, z; (iv) -x, -y+1, -z+1.

Data collection: CrysAlisPro CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlisPro CCD and CrysAlisPro RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlisPro CCD; data reduction: CrysAlisPro RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlisPro CCD and CrysAlisPro RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808015341/pv2084sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808015341/pv2084Isup2.hkl

checkCIF report

Comment top

Pramiracetam is a nootropic drug (Gouliaev & Senning, 1994) whose neurochemical properties have been investigated (Pugsley et al., 1983) also in view of possible applications as a memory aid (Mondadori et al., 1991) and for symptomatic treatment of Alzheimer's desease (Claus et al., 1991).

The contents of the asymmetric unit of the title compound (I) are shown in Fig 1. The atomic labelling is consistent with that previously adopted for the CH₃CN solvate (Bandoli et al., 1987) with which (I) is isomorphous and substantially isostructural, although the present conventional choice of labels for the axes does not match that of the previous report. There is a 3.8% reduction in the cell volume going from the solvated form to the present one, due to contraction of the two longest cell axes. The packing (Fig. 2) is controlled by a network of hydrogen bonds. The HSO₄^- anion behaves as a hydrogen bond donor towards a carbonylic oxygen and acts as acceptor of two hydrogen bonds from the aminic and ammonium N atoms (details of hydrogen-bonding geometry have been provided in Table 1). In this way two centrosymmetric and adjacent loops, consisting of 14 and 18 non-hydrogen atoms, respectively, are formed. Each loop has contributions from parts of two anions and two cations and each of these ions contributes to two contiguous loops which share the N2—H2···O3—S strand. Such arrangement, combined with the operation of the c translation, generates ribbons in the structure (these were parallel to the a direction in the previously reported structure of the solvated form, due to the different labelling of cell axes). In the case of the CH₃CN solvate the solvent molecules occupy large voids among the ribbons and are not involved in the network of hydrogen bonds. The largest difference in the conformation of the cation between the two structures is found for the C1—N1—C5—C6 torsion angle, whose value of -94.6 (2)° for (I) is significantly smaller than that, of -105.4(1.2)°, found for the structure of the solvate. The structure of (I) is stabilized by non-classical intermolecular and intramolecular hydrogen bonds of the type C—H···O (Table 1).

Related literature top

For related literature, see: Claus et al. (1991); Gouliaev & Senning (1994); Mondadori et al. (1991); Pugsley et al. (1983). For a related structure, see: Bandoli et al. (1987).

Experimental top

Samples of pramiracetam were kindly provided by SIMS (SIMS srl, Reggello Firenze, Italy). Crystals of (I), suitable for X-ray diffraction analysis, were obtained by slow evaporation from 1:3 2-propanol:acetone solutions.

Computing details top

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis PRO CCD (Oxford Diffraction, 2006); data reduction: CrysAlis PRO RED (Oxford Diffraction, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the content of the asymmetric unit of (I). Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view of the crystal packing in the structure of (I), showing the presence of ribbons formed by hydrogen–bonded ions. Hydrogen bonds are denoted by dashed lines. Only hydrogen atoms involved in the formation of hydrogen bonds are shown.

Diisopropyl{2-[2-(2-oxopyrrolidin-1-yl)acetamido]ethyl}ammonium hydrogen sulfate top

Crystal data top

C₁₄H₂₈N₃O₂⁺·HSO₄⁻	Z = 2
M_r = 367.46	F(000) = 396
Triclinic, P1	D_x = 1.311 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 6.7834 (3) Å	Cell parameters from 6722 reflections
b = 11.1755 (4) Å	θ = 4.6–72.4°
c = 12.9012 (6) Å	µ = 1.85 mm⁻¹
α = 72.165 (4)°	T = 170 K
β = 89.394 (4)°	Prism, pale yellow
γ = 89.509 (3)°	0.50 × 0.25 × 0.10 mm
V = 930.95 (7) Å³

Data collection top

Oxford Diffraction Xcalibur PX Ultra CCD diffractometer	3356 independent reflections
Radiation source: fine-focus sealed tube	3253 reflections with I > 2σ(I)
Oxford Diffraction Enhance ULTRA assembly monochromator	R_int = 0.018
Detector resolution: 8.1241 pixels mm^-1	θ_max = 72.7°, θ_min = 4.6°
ω scans	h = −8→8
Absorption correction: multi-scan (ABSPACK in CrysAlis PRO RED; Oxford Diffraction, 2006)	k = −13→13
T_min = 0.762, T_max = 1.000	l = −15→15
7656 measured reflections

Refinement top

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0779P)² + 0.7081P] where P = (F_o² + 2F_c²)/3
3356 reflections	(Δ/σ)_max < 0.001
230 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.57 e Å⁻³

Crystal data top

C₁₄H₂₈N₃O₂⁺·HSO₄⁻	γ = 89.509 (3)°
M_r = 367.46	V = 930.95 (7) Å³
Triclinic, P1	Z = 2
a = 6.7834 (3) Å	Cu Kα radiation
b = 11.1755 (4) Å	µ = 1.85 mm⁻¹
c = 12.9012 (6) Å	T = 170 K
α = 72.165 (4)°	0.50 × 0.25 × 0.10 mm
β = 89.394 (4)°

Data collection top

Oxford Diffraction Xcalibur PX Ultra CCD diffractometer	3356 independent reflections
Absorption correction: multi-scan (ABSPACK in CrysAlis PRO RED; Oxford Diffraction, 2006)	3253 reflections with I > 2σ(I)
T_min = 0.762, T_max = 1.000	R_int = 0.018
7656 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.45 e Å⁻³
3356 reflections	Δρ_min = −0.57 e Å⁻³
230 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S	0.38398 (7)	0.68601 (4)	0.65914 (4)	0.02428 (17)
O3	0.5651 (2)	0.65687 (14)	0.72078 (13)	0.0327 (4)
O4	0.4059 (2)	0.78663 (14)	0.55696 (12)	0.0308 (3)
O5	0.2944 (2)	0.57503 (15)	0.64603 (14)	0.0386 (4)
O6	0.2374 (3)	0.74531 (16)	0.72349 (14)	0.0384 (4)
H6	0.234 (5)	0.703 (3)	0.795 (3)	0.058*
N1	1.0351 (2)	0.37637 (16)	0.93852 (14)	0.0254 (4)
C1	0.9684 (3)	0.33125 (18)	1.04001 (16)	0.0243 (4)
O1	0.7977 (2)	0.34687 (14)	1.06959 (12)	0.0289 (3)
C2	1.1312 (3)	0.2564 (2)	1.11073 (17)	0.0287 (4)
H21	1.1096	0.1649	1.1271	0.034*
H22	1.1402	0.2768	1.1800	0.034*
C3	1.3171 (3)	0.2979 (2)	1.04077 (18)	0.0328 (5)
H31	1.3827	0.3679	1.0584	0.039*
H32	1.4116	0.2272	1.0515	0.039*
C4	1.2393 (3)	0.3403 (2)	0.92434 (18)	0.0310 (5)
H41	1.3151	0.4126	0.8779	0.037*
H42	1.2451	0.2710	0.8916	0.037*
C5	0.9126 (3)	0.44164 (18)	0.84733 (17)	0.0267 (4)
H51	0.9903	0.5092	0.7960	0.032*
H52	0.8002	0.4815	0.8740	0.032*
C6	0.8339 (3)	0.35436 (18)	0.78717 (16)	0.0254 (4)
O2	0.8971 (2)	0.24667 (13)	0.80310 (13)	0.0322 (4)
N2	0.6967 (3)	0.40757 (16)	0.71317 (14)	0.0268 (4)
H2	0.649 (4)	0.479 (3)	0.711 (2)	0.032*
C7	0.6169 (3)	0.34383 (19)	0.64051 (17)	0.0268 (4)
H71	0.7204	0.2906	0.6220	0.032*
H72	0.5733	0.4067	0.5722	0.032*
C8	0.4429 (3)	0.26239 (18)	0.69493 (16)	0.0254 (4)
H81	0.4831	0.2079	0.7678	0.031*
H82	0.3340	0.3173	0.7052	0.031*
N3	0.3696 (2)	0.18130 (15)	0.62949 (14)	0.0236 (4)
H3	0.449 (4)	0.197 (2)	0.564 (2)	0.028*
C9	0.3977 (3)	0.04104 (18)	0.69036 (18)	0.0289 (4)
H9	0.3453	−0.0071	0.6429	0.035*
C10	0.2806 (4)	0.0020 (2)	0.7957 (2)	0.0398 (5)
H101	0.1418	0.0254	0.7806	0.060*
H102	0.3327	0.0445	0.8456	0.060*
H103	0.2914	−0.0892	0.8291	0.060*
C11	0.6165 (3)	0.0111 (2)	0.70570 (19)	0.0342 (5)
H111	0.6351	−0.0801	0.7359	0.051*
H112	0.6708	0.0525	0.7559	0.051*
H113	0.6847	0.0415	0.6352	0.051*
C12	0.1589 (3)	0.21577 (18)	0.58962 (17)	0.0264 (4)
H12	0.0700	0.2061	0.6540	0.032*
C13	0.0884 (3)	0.1305 (2)	0.5264 (2)	0.0341 (5)
H131	−0.0412	0.1593	0.4953	0.051*
H132	0.0780	0.0443	0.5754	0.051*
H133	0.1825	0.1328	0.4677	0.051*
C14	0.1534 (3)	0.35207 (19)	0.51788 (18)	0.0297 (4)
H141	0.0187	0.3748	0.4923	0.045*
H142	0.2418	0.3626	0.4552	0.045*
H143	0.1963	0.4067	0.5599	0.045*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0230 (3)	0.0252 (3)	0.0239 (3)	0.00295 (18)	−0.0020 (2)	−0.00645 (19)
O3	0.0279 (8)	0.0345 (8)	0.0357 (8)	0.0053 (6)	−0.0098 (7)	−0.0106 (6)
O4	0.0319 (7)	0.0303 (7)	0.0256 (8)	0.0063 (6)	0.0024 (6)	−0.0022 (6)
O5	0.0385 (9)	0.0306 (8)	0.0474 (10)	−0.0018 (6)	−0.0117 (7)	−0.0125 (7)
O6	0.0424 (9)	0.0405 (9)	0.0283 (8)	0.0153 (7)	0.0044 (7)	−0.0053 (7)
N1	0.0230 (8)	0.0282 (8)	0.0241 (9)	0.0020 (6)	−0.0028 (7)	−0.0067 (7)
C1	0.0241 (9)	0.0234 (9)	0.0252 (10)	−0.0011 (7)	−0.0019 (8)	−0.0072 (7)
O1	0.0231 (7)	0.0332 (8)	0.0289 (8)	0.0015 (6)	0.0000 (6)	−0.0076 (6)
C2	0.0264 (10)	0.0312 (10)	0.0266 (10)	0.0037 (8)	−0.0050 (8)	−0.0062 (8)
C3	0.0243 (10)	0.0404 (12)	0.0331 (12)	0.0042 (8)	−0.0041 (9)	−0.0104 (9)
C4	0.0248 (10)	0.0379 (11)	0.0294 (11)	0.0019 (8)	0.0013 (9)	−0.0091 (9)
C5	0.0295 (10)	0.0252 (9)	0.0244 (10)	0.0024 (8)	−0.0043 (8)	−0.0063 (8)
C6	0.0258 (9)	0.0259 (9)	0.0232 (10)	0.0002 (7)	0.0007 (8)	−0.0057 (8)
O2	0.0353 (8)	0.0266 (7)	0.0358 (8)	0.0074 (6)	−0.0075 (7)	−0.0111 (6)
N2	0.0289 (9)	0.0230 (8)	0.0284 (9)	0.0009 (7)	−0.0062 (7)	−0.0073 (7)
C7	0.0274 (10)	0.0274 (10)	0.0254 (10)	−0.0018 (8)	−0.0034 (8)	−0.0076 (8)
C8	0.0256 (9)	0.0260 (9)	0.0246 (10)	0.0001 (7)	−0.0019 (8)	−0.0076 (8)
N3	0.0220 (8)	0.0221 (8)	0.0256 (9)	0.0010 (6)	−0.0015 (7)	−0.0057 (6)
C9	0.0315 (11)	0.0209 (9)	0.0314 (11)	0.0025 (8)	−0.0032 (9)	−0.0038 (8)
C10	0.0436 (13)	0.0301 (11)	0.0390 (13)	0.0002 (9)	0.0036 (11)	−0.0007 (9)
C11	0.0336 (11)	0.0307 (11)	0.0355 (12)	0.0085 (9)	−0.0063 (9)	−0.0062 (9)
C12	0.0213 (9)	0.0265 (10)	0.0304 (11)	0.0009 (7)	−0.0007 (8)	−0.0074 (8)
C13	0.0282 (10)	0.0330 (11)	0.0430 (13)	0.0013 (8)	−0.0073 (9)	−0.0145 (10)
C14	0.0262 (10)	0.0269 (10)	0.0335 (11)	0.0043 (8)	−0.0033 (9)	−0.0056 (8)

Geometric parameters (Å, º) top

S—O5	1.4422 (16)	C7—H71	0.9900
S—O3	1.4504 (14)	C7—H72	0.9900
S—O4	1.4543 (15)	C8—N3	1.505 (2)
S—O6	1.5574 (16)	C8—H81	0.9900
O6—H6	0.90 (4)	C8—H82	0.9900
N1—C1	1.327 (3)	N3—C12	1.530 (2)
N1—C5	1.446 (2)	N3—C9	1.534 (2)
N1—C4	1.465 (3)	N3—H3	0.97 (3)
C1—O1	1.243 (2)	C9—C10	1.512 (3)
C1—C2	1.514 (3)	C9—C11	1.521 (3)
C2—C3	1.533 (3)	C9—H9	1.0000
C2—H21	0.9900	C10—H101	0.9800
C2—H22	0.9900	C10—H102	0.9800
C3—C4	1.528 (3)	C10—H103	0.9800
C3—H31	0.9900	C11—H111	0.9800
C3—H32	0.9900	C11—H112	0.9800
C4—H41	0.9900	C11—H113	0.9800
C4—H42	0.9900	C12—C13	1.514 (3)
C5—C6	1.523 (3)	C12—C14	1.521 (3)
C5—H51	0.9900	C12—H12	1.0000
C5—H52	0.9900	C13—H131	0.9800
C6—O2	1.231 (2)	C13—H132	0.9800
C6—N2	1.339 (3)	C13—H133	0.9800
N2—C7	1.451 (2)	C14—H141	0.9800
N2—H2	0.86 (3)	C14—H142	0.9800
C7—C8	1.525 (3)	C14—H143	0.9800

O5—S—O3	111.94 (9)	N3—C8—C7	112.54 (16)
O5—S—O4	112.97 (10)	N3—C8—H81	109.1
O3—S—O4	113.20 (9)	C7—C8—H81	109.1
O5—S—O6	108.27 (10)	N3—C8—H82	109.1
O3—S—O6	107.71 (9)	C7—C8—H82	109.1
O4—S—O6	102.03 (9)	H81—C8—H82	107.8
S—O6—H6	113 (2)	C8—N3—C12	112.04 (15)
C1—N1—C5	123.65 (17)	C8—N3—C9	111.57 (15)
C1—N1—C4	113.69 (16)	C12—N3—C9	113.44 (15)
C5—N1—C4	122.23 (17)	C8—N3—H3	108.8 (14)
O1—C1—N1	124.46 (18)	C12—N3—H3	104.9 (14)
O1—C1—C2	126.64 (18)	C9—N3—H3	105.5 (15)
N1—C1—C2	108.87 (17)	C10—C9—C11	113.40 (19)
C1—C2—C3	103.44 (17)	C10—C9—N3	111.46 (18)
C1—C2—H21	111.1	C11—C9—N3	109.53 (16)
C3—C2—H21	111.1	C10—C9—H9	107.4
C1—C2—H22	111.1	C11—C9—H9	107.4
C3—C2—H22	111.1	N3—C9—H9	107.4
H21—C2—H22	109.0	C9—C10—H101	109.5
C4—C3—C2	103.68 (16)	C9—C10—H102	109.5
C4—C3—H31	111.0	H101—C10—H102	109.5
C2—C3—H31	111.0	C9—C10—H103	109.5
C4—C3—H32	111.0	H101—C10—H103	109.5
C2—C3—H32	111.0	H102—C10—H103	109.5
H31—C3—H32	109.0	C9—C11—H111	109.5
N1—C4—C3	102.97 (17)	C9—C11—H112	109.5
N1—C4—H41	111.2	H111—C11—H112	109.5
C3—C4—H41	111.2	C9—C11—H113	109.5
N1—C4—H42	111.2	H111—C11—H113	109.5
C3—C4—H42	111.2	H112—C11—H113	109.5
H41—C4—H42	109.1	C13—C12—C14	110.05 (18)
N1—C5—C6	112.43 (16)	C13—C12—N3	110.61 (16)
N1—C5—H51	109.1	C14—C12—N3	109.11 (16)
C6—C5—H51	109.1	C13—C12—H12	109.0
N1—C5—H52	109.1	C14—C12—H12	109.0
C6—C5—H52	109.1	N3—C12—H12	109.0
H51—C5—H52	107.9	C12—C13—H131	109.5
O2—C6—N2	123.75 (18)	C12—C13—H132	109.5
O2—C6—C5	122.51 (18)	H131—C13—H132	109.5
N2—C6—C5	113.70 (17)	C12—C13—H133	109.5
C6—N2—C7	122.02 (17)	H131—C13—H133	109.5
C6—N2—H2	119.3 (17)	H132—C13—H133	109.5
C7—N2—H2	118.6 (17)	C12—C14—H141	109.5
N2—C7—C8	109.99 (17)	C12—C14—H142	109.5
N2—C7—H71	109.7	H141—C14—H142	109.5
C8—C7—H71	109.7	C12—C14—H143	109.5
N2—C7—H72	109.7	H141—C14—H143	109.5
C8—C7—H72	109.7	H142—C14—H143	109.5
H71—C7—H72	108.2

C5—N1—C1—O1	−5.0 (3)	O2—C6—N2—C7	−3.3 (3)
C4—N1—C1—O1	−177.65 (18)	C5—C6—N2—C7	174.22 (18)
C5—N1—C1—C2	173.48 (17)	C6—N2—C7—C8	87.1 (2)
C4—N1—C1—C2	0.8 (2)	N2—C7—C8—N3	−172.82 (15)
O1—C1—C2—C3	−165.6 (2)	C7—C8—N3—C12	−115.80 (18)
N1—C1—C2—C3	16.0 (2)	C7—C8—N3—C9	115.77 (18)
C1—C2—C3—C4	−25.4 (2)	C8—N3—C9—C10	62.2 (2)
C1—N1—C4—C3	−17.3 (2)	C12—N3—C9—C10	−65.5 (2)
C5—N1—C4—C3	169.93 (18)	C8—N3—C9—C11	−64.1 (2)
C2—C3—C4—N1	25.7 (2)	C12—N3—C9—C11	168.21 (18)
C1—N1—C5—C6	−94.6 (2)	C8—N3—C12—C13	−178.70 (17)
C4—N1—C5—C6	77.4 (2)	C9—N3—C12—C13	−51.3 (2)
N1—C5—C6—O2	−12.1 (3)	C8—N3—C12—C14	60.1 (2)
N1—C5—C6—N2	170.35 (18)	C9—N3—C12—C14	−172.46 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3	0.86 (3)	2.10 (3)	2.948 (2)	172 (2)
N3—H3···O4ⁱ	0.97 (3)	1.79 (3)	2.764 (2)	175 (2)
O6—H6···O1ⁱⁱ	0.90 (4)	1.68 (4)	2.559 (2)	167 (3)
C12—H12···O2ⁱⁱⁱ	1.00	2.40	3.362 (3)	162
C13—H131···O4^iv	0.98	2.59	3.559 (2)	171
C14—H143···O5	0.98	2.56	3.530 (2)	172

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z+2; (iii) x−1, y, z; (iv) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₄H₂₈N₃O₂⁺·HSO₄⁻
M_r	367.46
Crystal system, space group	Triclinic, P1
Temperature (K)	170
a, b, c (Å)	6.7834 (3), 11.1755 (4), 12.9012 (6)
α, β, γ (°)	72.165 (4), 89.394 (4), 89.509 (3)
V (Å³)	930.95 (7)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	1.85
Crystal size (mm)	0.50 × 0.25 × 0.10

Data collection
Diffractometer	Oxford Diffraction Xcalibur PX Ultra CCD diffractometer
Absorption correction	Multi-scan (ABSPACK in CrysAlis PRO RED; Oxford Diffraction, 2006)
T_min, T_max	0.762, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7656, 3356, 3253
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.619

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.132, 1.06
No. of reflections	3356
No. of parameters	230
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.57

Computer programs: CrysAlis PRO CCD (Oxford Diffraction, 2006), CrysAlis PRO RED (Oxford Diffraction, 2006), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3	0.86 (3)	2.10 (3)	2.948 (2)	172 (2)
N3—H3···O4ⁱ	0.97 (3)	1.79 (3)	2.764 (2)	175 (2)
O6—H6···O1ⁱⁱ	0.90 (4)	1.68 (4)	2.559 (2)	167 (3)
C12—H12···O2ⁱⁱⁱ	1.00	2.40	3.362 (3)	162
C13—H131···O4^iv	0.98	2.59	3.559 (2)	171
C14—H143···O5	0.98	2.56	3.530 (2)	172

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z+2; (iii) x−1, y, z; (iv) −x, −y+1, −z+1.

Acknowledgements

The authors acknowledge financial support from the Italian Ministero dell'Istruzione, dell'Universitá e della Ricerca.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bandoli, G., Nicolini, M., Pappalardo, G. C. & Grassi, A. (1987). J. Mol. Struct. 157, 311–320. CSD CrossRef CAS Web of Science Google Scholar
Claus, J. J., Ludwig, C., Mohr, E., Giuffra, M., Blin, J. & Chase, T. N. (1991). Neurology. 41, 570–574. CrossRef CAS PubMed Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
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Mondadori, C., Ducret, T. & Borkowski, J. (1991). Brain Res. 555, 107–111. CrossRef PubMed CAS Web of Science Google Scholar
Oxford Diffraction (2006). CrysAlisPro CCD and CrysAlisPro RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England. Google Scholar
Pugsley, T. A., Shih, Y. H., Coughenour, L. & Stewart, S. F. (1983). Drug Develop. Res. 3, 407–420. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 6| June 2008| Page o1160

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Diisoprop­yl{2-[2-(2-oxopyrrolidin-1-yl)acetamido]eth­yl}ammonium hydrogen sulfate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Diisopropyl{2-[2-(2-oxopyrrolidin-1-yl)acetamido]ethyl}ammonium hydrogen sulfate