(1S,2S)-2-Carboxy-1-(3-pyridiniometh-yl)pyrrolidin-1-ium dichloride hemihydrate.

In the title mol-ecule, C(11)H(16)N(2)O(2) (2+)·2Cl(-)·0.5H(2)O, all N atoms are protonated. In the crystal structure, the organic cation and Cl(-) ions are linked by N-H⋯Cl and O-H⋯Cl hydrogen bonds, forming a one-dimensional infinite ribbon extending parallel to the (110) plane.

Related literature

For the chemistry of amino acid derivatives, see: Fu et al. (2007 ▶); Dai & Fu (2008 ▶); Wen (2008 ▶).

Experimental

Crystal data

C11H16N2O2 2+·2Cl−·0.5H2O

M = 288.17

Monoclinic,

a = 13.070 (5) Å

b = 6.9215 (15) Å

c = 15.027 (5) Å

β = 97.90 (2)°

V = 1346.5 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.48 mm−1

T = 298 (2) K

0.24 × 0.20 × 0.18 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.892, T max = 0.918

6833 measured reflections

3154 independent reflections

2893 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.085

S = 1.07

3154 reflections

172 parameters

4 restraints

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 1420 Friedel pairs

Flack parameter: 0.02 (5)

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶), ORTEPIII (Burnett & Johnson, 1996 ▶) and ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S160053680802922X/dn2371sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802922X/dn2371Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H16N2O22+·2Cl−·0.5H2O	F(000) = 604
Mr = 288.17	Dx = 1.416 Mg m−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 3101 reflections
a = 13.070 (5) Å	θ = 3.2–27.5°
b = 6.9215 (15) Å	µ = 0.48 mm−1
c = 15.027 (5) Å	T = 298 K
β = 97.90 (2)°	Block, colorless
V = 1346.5 (7) Å3	0.24 × 0.20 × 0.18 mm
Z = 4

Rigaku Mercury2 diffractometer	3154 independent reflections
Radiation source: fine-focus sealed tube	2893 reflections with I > 2σ(I)
graphite	Rint = 0.020
Detector resolution: 13.6612 pixels mm-1	θmax = 27.9°, θmin = 2.7°
ω scans	h = −17→17
Absorption correction: multi-scan (CrystalClea; Rigaku, 2005)	k = −9→9
Tmin = 0.892, Tmax = 0.918	l = −19→19
6833 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033	H-atom parameters constrained
wR(F2) = 0.085	w = 1/[σ2(Fo2) + (0.0472P)2 + 0.0829P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
3154 reflections	Δρmax = 0.16 e Å−3
172 parameters	Δρmin = −0.21 e Å−3
4 restraints	Absolute structure: Flack (1983), 1420 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.02 (5)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Uiso*/Ueq	Occ. (<1)
C1	0.49977 (16)	0.5154 (3)	0.12620 (12)	0.0360 (4)
H1	0.4894	0.6481	0.1286	0.043*
C2	0.43049 (14)	0.3904 (3)	0.15703 (11)	0.0314 (4)
C3	0.44775 (16)	0.1940 (3)	0.15117 (15)	0.0438 (5)
H3	0.4014	0.1066	0.1704	0.053*
C4	0.5344 (2)	0.1274 (3)	0.11651 (17)	0.0515 (6)
H4	0.5471	−0.0045	0.1136	0.062*
C5	0.60084 (15)	0.2572 (4)	0.08674 (13)	0.0421 (5)
H5	0.6585	0.2142	0.0626	0.051*
C6	0.33723 (16)	0.4708 (4)	0.19263 (13)	0.0404 (5)
H6A	0.3133	0.5847	0.1583	0.049*
H6B	0.2822	0.3757	0.1849	0.049*
C7	0.40028 (17)	0.3566 (3)	0.35056 (14)	0.0421 (5)	0.50
H71	0.3900	0.2356	0.3180	0.051*	0.50
H72	0.4736	0.3723	0.3707	0.051*	0.50
C8	0.3426 (3)	0.3553 (7)	0.4284 (3)	0.0439 (10)	0.50
H81	0.3887	0.3327	0.4837	0.053*	0.50
H82	0.2899	0.2556	0.4217	0.053*	0.50
C9	0.29262 (18)	0.5601 (4)	0.42867 (14)	0.0474 (5)	0.50
H91	0.2306	0.5587	0.4574	0.057*	0.50
H92	0.3407	0.6544	0.4582	0.057*	0.50
C7'	0.40028 (17)	0.3566 (3)	0.35056 (14)	0.0421 (5)	0.50
H71'	0.4718	0.3271	0.3455	0.051*	0.50
H72'	0.3586	0.2415	0.3376	0.051*	0.50
C8'	0.3884 (4)	0.4405 (8)	0.4435 (3)	0.0474 (11)	0.50
H81'	0.3816	0.3379	0.4862	0.057*	0.50
H82'	0.4477	0.5194	0.4661	0.057*	0.50
C9'	0.29262 (18)	0.5601 (4)	0.42867 (14)	0.0474 (5)	0.50
H91'	0.3031	0.6808	0.4614	0.057*	0.50
H92'	0.2358	0.4916	0.4498	0.057*	0.50
C10	0.26803 (14)	0.5995 (3)	0.32803 (12)	0.0313 (4)
H10	0.2075	0.5229	0.3038	0.038*
C11	0.24701 (14)	0.8082 (3)	0.30450 (12)	0.0346 (4)
Cl1	0.67434 (4)	0.78893 (6)	0.01140 (3)	0.04105 (13)
Cl2	0.06792 (4)	1.25793 (8)	0.32514 (4)	0.04764 (15)
N1	0.58244 (13)	0.4454 (3)	0.09258 (11)	0.0382 (4)
H1A	0.6252	0.5256	0.0741	0.046*
N2	0.36060 (11)	0.5234 (2)	0.29028 (9)	0.0285 (3)
H2	0.4098	0.6173	0.2959	0.034*
O1	0.16413 (12)	0.8657 (3)	0.33754 (12)	0.0583 (5)
H1B	0.1530	0.9797	0.3249	0.088*
O2	0.29780 (12)	0.9077 (2)	0.26191 (11)	0.0534 (4)
O1W	0.4711 (9)	−0.0105 (7)	0.4873 (10)	0.123 (5)	0.50
H1W	0.4729	−0.0753	0.5396	0.185*

	U11	U22	U33	U12	U13	U23
C1	0.0464 (12)	0.0296 (10)	0.0320 (9)	−0.0014 (8)	0.0055 (8)	−0.0005 (7)
C2	0.0344 (9)	0.0324 (10)	0.0279 (9)	0.0017 (8)	0.0065 (7)	−0.0020 (7)
C3	0.0482 (13)	0.0338 (11)	0.0545 (13)	−0.0074 (9)	0.0249 (10)	−0.0030 (9)
C4	0.0657 (16)	0.0318 (11)	0.0635 (14)	0.0076 (10)	0.0314 (12)	0.0003 (10)
C5	0.0372 (9)	0.0516 (13)	0.0401 (10)	0.0091 (10)	0.0140 (8)	0.0024 (9)
C6	0.0343 (10)	0.0552 (14)	0.0321 (9)	0.0065 (9)	0.0059 (8)	−0.0093 (8)
C7	0.0484 (12)	0.0362 (11)	0.0434 (11)	0.0035 (9)	0.0125 (9)	0.0089 (9)
C8	0.038 (2)	0.050 (3)	0.044 (2)	−0.004 (2)	0.0081 (19)	0.010 (2)
C9	0.0525 (13)	0.0551 (15)	0.0377 (11)	0.0030 (11)	0.0174 (9)	0.0035 (10)
C7'	0.0484 (12)	0.0362 (11)	0.0434 (11)	0.0035 (9)	0.0125 (9)	0.0089 (9)
C8'	0.057 (3)	0.050 (3)	0.037 (2)	0.002 (2)	0.013 (2)	0.007 (2)
C9'	0.0525 (13)	0.0551 (15)	0.0377 (11)	0.0030 (11)	0.0174 (9)	0.0035 (10)
C10	0.0264 (9)	0.0338 (10)	0.0355 (9)	−0.0026 (7)	0.0110 (7)	−0.0032 (7)
C11	0.0337 (9)	0.0380 (11)	0.0340 (9)	−0.0001 (8)	0.0111 (7)	−0.0036 (8)
Cl1	0.0415 (2)	0.0343 (3)	0.0504 (3)	−0.0046 (2)	0.01712 (19)	−0.0065 (2)
Cl2	0.0374 (2)	0.0372 (3)	0.0681 (3)	−0.0070 (2)	0.0062 (2)	−0.0065 (2)
N1	0.0363 (8)	0.0447 (10)	0.0351 (8)	−0.0105 (7)	0.0098 (7)	0.0028 (7)
N2	0.0252 (7)	0.0299 (8)	0.0315 (7)	−0.0032 (6)	0.0077 (6)	−0.0023 (6)
O1	0.0527 (9)	0.0428 (9)	0.0882 (12)	0.0126 (8)	0.0411 (9)	0.0056 (9)
O2	0.0530 (9)	0.0414 (9)	0.0724 (10)	0.0029 (8)	0.0320 (8)	0.0112 (8)
O1W	0.201 (15)	0.071 (3)	0.112 (8)	0.044 (5)	0.077 (9)	0.033 (5)

C1—N1	1.344 (3)	C8—C9	1.561 (5)
C1—C2	1.378 (3)	C8—H81	0.9700
C1—H1	0.9300	C8—H82	0.9700
C2—C3	1.383 (3)	C9—C10	1.527 (3)
C2—C6	1.504 (3)	C9—H91	0.9700
C3—C4	1.389 (3)	C9—H92	0.9700
C3—H3	0.9300	C8'—H81'	0.9700
C4—C5	1.366 (3)	C8'—H82'	0.9700
C4—H4	0.9300	C10—N2	1.501 (2)
C5—N1	1.330 (3)	C10—C11	1.503 (3)
C5—H5	0.9300	C10—H10	0.9800
C6—N2	1.502 (2)	C11—O2	1.201 (2)
C6—H6A	0.9700	C11—O1	1.314 (2)
C6—H6B	0.9700	N1—H1A	0.8600
C7—C8	1.476 (5)	N2—H2	0.9100
C7—N2	1.514 (3)	O1—H1B	0.8200
C7—H71	0.9700	O1W—H1W	0.9015
C7—H72	0.9700
N1—C1—C2	119.96 (19)	C7—C8—H82	110.8
N1—C1—H1	120.0	C9—C8—H82	110.8
C2—C1—H1	120.0	H81—C8—H82	108.9
C1—C2—C3	118.38 (18)	C10—C9—C8	101.0 (2)
C1—C2—C6	119.32 (19)	C10—C9—H91	111.6
C3—C2—C6	122.27 (18)	C8—C9—H91	111.6
C2—C3—C4	119.93 (19)	C10—C9—H92	111.6
C2—C3—H3	120.0	C8—C9—H92	111.6
C4—C3—H3	120.0	H91—C9—H92	109.4
C5—C4—C3	119.5 (2)	H81'—C8'—H82'	108.8
C5—C4—H4	120.3	N2—C10—C11	112.30 (15)
C3—C4—H4	120.3	N2—C10—C9	103.93 (16)
N1—C5—C4	119.58 (19)	C11—C10—C9	114.30 (16)
N1—C5—H5	120.2	N2—C10—H10	108.7
C4—C5—H5	120.2	C11—C10—H10	108.7
N2—C6—C2	111.79 (16)	C9—C10—H10	108.7
N2—C6—H6A	109.3	O2—C11—O1	124.9 (2)
C2—C6—H6A	109.3	O2—C11—C10	125.44 (18)
N2—C6—H6B	109.3	O1—C11—C10	109.62 (16)
C2—C6—H6B	109.3	C5—N1—C1	122.67 (18)
H6A—C6—H6B	107.9	C5—N1—H1A	118.7
C8—C7—N2	108.0 (2)	C1—N1—H1A	118.7
C8—C7—H71	110.1	C10—N2—C6	112.84 (14)
N2—C7—H71	110.1	C10—N2—C7	105.62 (14)
C8—C7—H72	110.1	C6—N2—C7	114.01 (16)
N2—C7—H72	110.1	C10—N2—H2	108.0
H71—C7—H72	108.4	C6—N2—H2	108.0
C7—C8—C9	104.8 (3)	C7—N2—H2	108.0
C7—C8—H81	110.8	C11—O1—H1B	109.5
C9—C8—H81	110.8

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···Cl2	0.82	2.22	2.9869 (19)	155.
N1—H1A···Cl1	0.86	2.19	2.9980 (19)	157.
N2—H2···Cl2i	0.91	2.27	3.1405 (18)	159.
O1W—H1W···Cl2ii	0.90	2.46	3.342 (15)	166.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1B⋯Cl2	0.82	2.22	2.9869 (19)	155
N1—H1A⋯Cl1	0.86	2.19	2.9980 (19)	157
N2—H2⋯Cl2i	0.91	2.27	3.1405 (18)	159
O1W—H1W⋯Cl2ii	0.90	2.46	3.342 (15)	166

Symmetry codes: (i) ; (ii) .