4-{2-[3-(2-Ammonioacetamido)propanamido]ethyl}-1H-imidazol-3-ium dichloride.

Mol-ecules of the title compound, Gly-β-Ala-Histamine dihydro-chloride, C(10)H(19)N(5)O(2) (2+)·2Cl(-), are linked by N-H⋯O and N-H⋯Cl hydrogen bonds into two-dimensional polymeric sheets parallel to the (011) plane, forming a stacked structure along the a axis. The parallel layers are also inter-linked alternately by different N-H⋯Cl hydrogen bonds, forming a three-dimensional framework.

Related literature

For the complexation abilities of oligopeptides towards different metals, see: Kozlowski et al. (1999 ▶); Gajda et al. (1996 ▶). For bond lengths and angles in other oligopeptides, see: Itoh et al. (1977 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related literature, see: Henry et al. (1993 ▶).

Experimental

Crystal data

C10H19N5O2 2+·2Cl−

M = 312.20

Triclinic,

a = 7.2923 (10) Å

b = 8.2215 (11) Å

c = 13.0767 (15) Å

α = 81.702 (11)°

β = 77.863 (11)°

γ = 69.543 (12)°

V = 715.98 (16) Å3

Z = 2

Mo Kα radiation

μ = 0.46 mm−1

T = 110 (2) K

0.30 × 0.20 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur-Saphire2 CCD diffractometer

Absorption correction: numerical (ABSORB; DeTitta, 1985 ▶) T min = 0.874, T max = 0.952

12727 measured reflections

3307 independent reflections

1798 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.111

S = 0.97

3307 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.35 e Å−3

Data collection: CryslisCCD (Oxford Diffraction, 2003 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2003 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808035952/cs2096sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035952/cs2096Isup2.hkl

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

C10H19N5O22+·2Cl–	Z = 2
Mr = 312.20	F000 = 328
Triclinic, P1	Dx = 1.448 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.2923 (10) Å	Cell parameters from 12727 reflections
b = 8.2215 (11) Å	θ = 2.7–29.2º
c = 13.0767 (15) Å	µ = 0.46 mm−1
α = 81.702 (11)º	T = 110 (2) K
β = 77.863 (11)º	Prism, colourless
γ = 69.543 (12)º	0.30 × 0.20 × 0.12 mm
V = 715.98 (16) Å3

Oxford Diffraction Xcalibur-Saphire2 CCD diffractometer	3307 independent reflections
Radiation source: fine-focus sealed tube	1798 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.061
T = 110(2) K	θmax = 29.2º
ω scan	θmin = 2.7º
Absorption correction: numerical(ABSORB; DeTitta, 1985)	h = −9→9
Tmin = 0.874, Tmax = 0.952	k = −11→11
12727 measured reflections	l = −17→16

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)] = 0.046	H-atom parameters constrained
wR(F2) = 0.111	w = 1/[σ2(Fo2) + (0.0489P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max < 0.001
3307 reflections	Δρmax = 0.51 e Å−3
172 parameters	Δρmin = −0.35 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

	x	y	z	Uiso*/Ueq
O1	0.7290 (4)	0.3622 (3)	0.54649 (15)	0.0302 (6)
O2	0.7180 (3)	−0.1826 (2)	0.77310 (14)	0.0255 (5)
N1	0.7705 (4)	1.0791 (3)	0.25403 (18)	0.0255 (6)
H1'	0.7720	1.0903	0.1859	0.031*
N2	0.7640 (4)	1.1387 (3)	0.40854 (18)	0.0230 (6)
H2'	0.7614	1.1961	0.4609	0.028*
N3	0.7314 (4)	0.5944 (3)	0.61436 (17)	0.0217 (6)
H3'	0.7289	0.6443	0.6701	0.026*
N4	0.7164 (4)	0.0643 (3)	0.83121 (17)	0.0205 (6)
H4'	0.7173	0.1161	0.8854	0.025*
N5	0.7507 (4)	−0.3688 (3)	0.95958 (18)	0.0223 (6)
H5C'	0.7717	−0.4211	1.0243	0.033*
H5B'	0.8438	−0.4329	0.9097	0.033*
H5A'	0.6275	−0.3610	0.9505	0.033*
C1	0.7671 (5)	1.2013 (4)	0.3094 (2)	0.0271 (7)
H1	0.7668	1.3152	0.2829	0.033*
C2	0.7655 (4)	0.9685 (3)	0.4167 (2)	0.0189 (7)
C3	0.7717 (5)	0.9304 (4)	0.3183 (2)	0.0222 (7)
H3	0.7759	0.8228	0.2977	0.027*
C4	0.7614 (5)	0.8637 (4)	0.5201 (2)	0.0217 (7)
H4B	0.6470	0.9288	0.5709	0.026*
H4A	0.8842	0.8465	0.5473	0.026*
C5	0.7448 (5)	0.6879 (3)	0.5113 (2)	0.0201 (7)
H5B	0.6251	0.7041	0.4814	0.024*
H5A	0.8626	0.6195	0.4638	0.024*
C6	0.7229 (4)	0.4335 (4)	0.6247 (2)	0.0217 (7)
C7	0.7099 (5)	0.3428 (3)	0.7336 (2)	0.0195 (7)
H7B	0.5899	0.4119	0.7796	0.023*
H7A	0.8276	0.3333	0.7634	0.023*
C8	0.7003 (5)	0.1626 (3)	0.7299 (2)	0.0203 (7)
H8B	0.5730	0.1730	0.7097	0.024*
H8A	0.8098	0.0998	0.6761	0.024*
C9	0.7297 (4)	−0.1029 (4)	0.8434 (2)	0.0190 (7)
C10	0.7655 (5)	−0.1917 (3)	0.9503 (2)	0.0202 (7)
H10B	0.8992	−0.1998	0.9607	0.024*
H10A	0.6660	−0.1223	1.0054	0.024*
Cl2	1.15091 (12)	−0.57052 (9)	0.81161 (5)	0.0251 (2)
Cl1	0.71393 (12)	1.24682 (9)	0.03128 (5)	0.0240 (2)

	U11	U22	U33	U12	U13	U23
O1	0.0512 (17)	0.0260 (12)	0.0199 (11)	−0.0198 (12)	−0.0059 (10)	−0.0041 (9)
O2	0.0408 (15)	0.0195 (11)	0.0184 (11)	−0.0124 (11)	−0.0042 (10)	−0.0036 (9)
N1	0.0291 (17)	0.0326 (15)	0.0148 (13)	−0.0124 (13)	−0.0004 (11)	−0.0010 (11)
N2	0.0277 (16)	0.0206 (14)	0.0224 (14)	−0.0095 (13)	−0.0025 (12)	−0.0060 (11)
N3	0.0330 (17)	0.0177 (13)	0.0162 (12)	−0.0125 (12)	0.0004 (11)	−0.0027 (10)
N4	0.0304 (16)	0.0170 (13)	0.0163 (12)	−0.0106 (12)	−0.0030 (11)	−0.0030 (10)
N5	0.0267 (16)	0.0202 (13)	0.0191 (13)	−0.0084 (12)	−0.0010 (11)	−0.0010 (10)
C1	0.0218 (19)	0.0225 (17)	0.0353 (19)	−0.0076 (15)	−0.0070 (15)	0.0070 (15)
C2	0.0193 (18)	0.0114 (15)	0.0254 (16)	−0.0051 (13)	−0.0008 (13)	−0.0032 (12)
C3	0.0227 (19)	0.0222 (17)	0.0223 (16)	−0.0085 (15)	−0.0035 (14)	−0.0018 (13)
C4	0.0229 (19)	0.0242 (16)	0.0186 (15)	−0.0093 (15)	−0.0029 (13)	−0.0009 (13)
C5	0.0232 (18)	0.0178 (15)	0.0180 (15)	−0.0053 (14)	−0.0033 (13)	−0.0019 (12)
C6	0.0210 (19)	0.0240 (17)	0.0202 (16)	−0.0080 (15)	−0.0023 (13)	−0.0023 (13)
C7	0.0255 (19)	0.0165 (15)	0.0151 (15)	−0.0070 (14)	−0.0011 (13)	−0.0008 (12)
C8	0.0228 (19)	0.0217 (16)	0.0186 (15)	−0.0100 (14)	−0.0031 (13)	−0.0026 (12)
C9	0.0128 (17)	0.0208 (16)	0.0230 (16)	−0.0062 (14)	0.0002 (13)	−0.0035 (13)
C10	0.0221 (18)	0.0154 (15)	0.0234 (16)	−0.0055 (14)	−0.0045 (14)	−0.0033 (12)
Cl2	0.0295 (5)	0.0243 (4)	0.0217 (4)	−0.0097 (4)	−0.0006 (3)	−0.0055 (3)
Cl1	0.0291 (5)	0.0241 (4)	0.0215 (4)	−0.0114 (4)	−0.0050 (3)	−0.0022 (3)

O1—C6	1.235 (3)	C1—H1	0.9500
O2—C9	1.237 (3)	C2—C3	1.356 (4)
N1—C1	1.311 (4)	C2—C4	1.495 (4)
N1—C3	1.378 (3)	C3—H3	0.9500
N1—H1'	0.8800	C4—C5	1.514 (4)
N2—C1	1.322 (4)	C4—H4B	0.9900
N2—C2	1.384 (3)	C4—H4A	0.9900
N2—H2'	0.8800	C5—H5B	0.9900
N3—C6	1.333 (3)	C5—H5A	0.9900
N3—C5	1.454 (3)	C6—C7	1.510 (4)
N3—H3'	0.8800	C7—C8	1.515 (3)
N4—C9	1.332 (3)	C7—H7B	0.9900
N4—C8	1.453 (3)	C7—H7A	0.9900
N4—H4'	0.8800	C8—H8B	0.9900
N5—C10	1.483 (3)	C8—H8A	0.9900
N5—H5C'	0.9100	C9—C10	1.510 (4)
N5—H5B'	0.9100	C10—H10B	0.9900
N5—H5A'	0.9100	C10—H10A	0.9900
C1—N1—C3	109.9 (2)	H4B—C4—H4A	107.9
C1—N1—H1'	125.0	N3—C5—C4	109.9 (2)
C3—N1—H1'	125.0	N3—C5—H5B	109.7
C1—N2—C2	109.1 (2)	C4—C5—H5B	109.7
C1—N2—H2'	125.4	N3—C5—H5A	109.7
C2—N2—H2'	125.4	C4—C5—H5A	109.7
C6—N3—C5	120.2 (2)	H5B—C5—H5A	108.2
C6—N3—H3'	119.9	O1—C6—N3	120.1 (3)
C5—N3—H3'	119.9	O1—C6—C7	122.2 (2)
C9—N4—C8	121.1 (2)	N3—C6—C7	117.8 (2)
C9—N4—H4'	119.4	C6—C7—C8	110.2 (2)
C8—N4—H4'	119.4	C6—C7—H7B	109.6
C10—N5—H5C'	109.5	C8—C7—H7B	109.6
C10—N5—H5B'	109.5	C6—C7—H7A	109.6
H5C'—N5—H5B'	109.5	C8—C7—H7A	109.6
C10—N5—H5A'	109.5	H7B—C7—H7A	108.1
H5C'—N5—H5A'	109.5	N4—C8—C7	110.9 (2)
H5B'—N5—H5A'	109.5	N4—C8—H8B	109.5
N1—C1—N2	108.3 (2)	C7—C8—H8B	109.5
N1—C1—H1	125.9	N4—C8—H8A	109.5
N2—C1—H1	125.9	C7—C8—H8A	109.5
C3—C2—N2	106.4 (2)	H8B—C8—H8A	108.0
C3—C2—C4	132.2 (2)	O2—C9—N4	123.5 (2)
N2—C2—C4	121.4 (2)	O2—C9—C10	121.6 (2)
C2—C3—N1	106.3 (2)	N4—C9—C10	114.9 (2)
C2—C3—H3	126.9	N5—C10—C9	110.0 (2)
N1—C3—H3	126.9	N5—C10—H10B	109.7
C2—C4—C5	111.9 (2)	C9—C10—H10B	109.7
C2—C4—H4B	109.2	N5—C10—H10A	109.7
C5—C4—H4B	109.2	C9—C10—H10A	109.7
C2—C4—H4A	109.2	H10B—C10—H10A	108.2
C5—C4—H4A	109.2

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1'···Cl1	0.88	2.27	3.083 (4)	153
N2—H2'···O1i	0.88	1.81	2.670 (4)	165
N3—H3'···O2i	0.88	2.07	2.927 (4)	165
N4—H4'···Cl1ii	0.88	2.31	3.192 (4)	178
N5—H5C'···Cl2iii	0.91	2.32	3.152 (4)	152
N5—H5B'···Cl2	0.91	2.32	3.191 (4)	160
N5—H5A'···Cl1iv	0.91	2.31	3.161 (4)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1′⋯Cl1	0.88	2.27	3.083 (4)	153
N2—H2′⋯O1i	0.88	1.81	2.670 (4)	165
N3—H3′⋯O2i	0.88	2.07	2.927 (4)	165
N4—H4′⋯Cl1ii	0.88	2.31	3.192 (4)	178
N5—H5C’⋯Cl2iii	0.91	2.32	3.152 (4)	152
N5—H5B′⋯Cl2	0.91	2.32	3.191 (4)	160
N5—H5A′⋯Cl1iv	0.91	2.31	3.161 (4)	156

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