4-(2,3-Dimethyl-phen-yl)piperazin-1-ium chloride monohydrate.

The title compound, C(12)H(19)N(2) (+)·Cl(-)·H(2)O, contains a network of 4-(2,3-dimethyl-phen-yl)piperazin-1-ium cations, water mol-ecules and chloride anions. The crystal packing is influenced by O-H⋯Cl, N-H⋯Cl, N-H⋯O, C-H⋯O and C-H⋯Cl hydrogen bonds, resulting in structure with an open-framework architecture.

Related literature

For related literature, see: Ben Gharbia et al. (2005 ▶, 2007 ▶); Bernstein et al. (1995 ▶); Pajewski et al. (2004 ▶); Sessler et al. (2003 ▶); Schmidtchen & Berge (1997 ▶). For the refinement weighting scheme, see: Prince (1982 ▶); Watkin (1994 ▶).

Experimental

Crystal data

C12H19N2 +·Cl−·H2O

M = 244.76

Triclinic,

a = 7.5439 (3) Å

b = 9.4204 (3) Å

c = 10.4347 (4) Å

α = 72.733 (2)°

β = 74.152 (2)°

γ = 70.250 (2)°

V = 654.05 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.28 mm−1

T = 150 K

0.13 × 0.12 × 0.09 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: none

5719 measured reflections

3073 independent reflections

2601 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.035

S = 1.10

2491 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.20 e Å−3

Data collection: COLLECT (Nonius, 2001 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: CRYSTALS.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808019016/cf2207sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019016/cf2207Isup2.hkl

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

C12H19N2+·Cl–·H2O	Z = 2
Mr = 244.76	F000 = 264
Triclinic, P1	Dx = 1.243 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71069 Å
a = 7.5439 (3) Å	Cell parameters from 2750 reflections
b = 9.4204 (3) Å	θ = 0.4–27.9º
c = 10.4347 (4) Å	µ = 0.28 mm−1
α = 72.733 (2)º	T = 150 K
β = 74.152 (2)º	Block, colorless
γ = 70.250 (2)º	0.13 × 0.12 × 0.09 mm
V = 654.05 (4) Å3

Nonius KappaCCD diffractometer	2601 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.016
T = 150 K	θmax = 27.9º
φ and ω scans	θmin = 2.1º
Absorption correction: none	h = −9→9
5719 measured reflections	k = −12→12
3073 independent reflections	l = −13→13

Refinement on F	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.036	w = [1-(Fo-Fc)2/36σ2(F)]2/[0.443T0(x) + 0.129T1(x) + 0.131T2(x)] where Ti are Chebychev polynomials and x = Fc/Fmax (Prince, 1982; Watkin, 1994)
wR(F2) = 0.035	(Δ/σ)max = 0.0004
S = 1.10	Δρmax = 0.25 e Å−3
2491 reflections	Δρmin = −0.20 e Å−3
145 parameters	Extinction correction: None
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
C1	−0.09326 (17)	0.26100 (14)	0.53871 (13)	0.0211
C2	−0.08069 (18)	0.18226 (14)	0.67481 (13)	0.0224
C3	−0.24822 (19)	0.15986 (14)	0.76843 (13)	0.0243
C4	−0.42381 (18)	0.21709 (15)	0.72522 (14)	0.0270
C5	−0.43454 (18)	0.29399 (16)	0.59077 (14)	0.0285
C6	−0.26999 (18)	0.31526 (15)	0.49687 (13)	0.0255
C7	0.18840 (18)	0.14963 (15)	0.38467 (14)	0.0276
C8	0.38588 (19)	0.16564 (16)	0.30991 (15)	0.0313
C9	0.24578 (19)	0.45044 (15)	0.26085 (13)	0.0260
C10	0.05184 (17)	0.42554 (14)	0.33543 (13)	0.0230
C11	0.1080 (2)	0.12337 (17)	0.72288 (15)	0.0320
C12	−0.2398 (2)	0.07656 (18)	0.91485 (14)	0.0353
Cl1	0.77820 (5)	0.34324 (4)	0.11653 (4)	0.0340
O1	0.78625 (14)	0.68790 (12)	0.00994 (10)	0.0353
N1	0.07922 (14)	0.28419 (12)	0.44468 (11)	0.0216
N2	0.36750 (15)	0.31276 (13)	0.20308 (12)	0.0278
H1	0.7848	0.5995	0.0526	0.0528*
H2	0.9007	0.6873	−0.0182	0.0528*
H3	0.4845	0.3270	0.1661	0.0430*
H4	0.3144	0.3085	0.1358	0.0437*
H5	−0.5385	0.2058	0.7916	0.0322*
H6	−0.5565	0.3352	0.5610	0.0341*
H7	−0.2770	0.3659	0.4045	0.0295*
H8	0.1198	0.1410	0.3200	0.0321*
H9	0.2040	0.0561	0.4575	0.0315*
H10	0.4588	0.0790	0.2644	0.0369*
H11	0.4582	0.1695	0.3749	0.0356*
H12	0.3114	0.4642	0.3220	0.0314*
H13	0.2299	0.5429	0.1850	0.0309*
H14	−0.0266	0.5162	0.3773	0.0269*
H15	−0.0141	0.4180	0.2684	0.0273*
H16	0.2087	0.1594	0.6514	0.0467*
H17	0.1484	0.0098	0.7464	0.0473*
H18	0.0940	0.1606	0.8047	0.0484*
H19	−0.1476	−0.0282	0.9197	0.0537*
H20	−0.2011	0.1364	0.9587	0.0526*
H21	−0.3671	0.0679	0.9639	0.0532*

	U11	U22	U33	U12	U13	U23
C1	0.0204 (5)	0.0193 (5)	0.0239 (6)	−0.0065 (4)	−0.0025 (4)	−0.0057 (5)
C2	0.0250 (6)	0.0184 (5)	0.0251 (6)	−0.0079 (5)	−0.0054 (5)	−0.0040 (5)
C3	0.0289 (6)	0.0211 (6)	0.0243 (6)	−0.0104 (5)	−0.0022 (5)	−0.0059 (5)
C4	0.0243 (6)	0.0269 (6)	0.0298 (7)	−0.0099 (5)	0.0020 (5)	−0.0098 (5)
C5	0.0213 (6)	0.0308 (7)	0.0331 (7)	−0.0073 (5)	−0.0039 (5)	−0.0081 (6)
C6	0.0231 (6)	0.0273 (6)	0.0250 (6)	−0.0079 (5)	−0.0040 (5)	−0.0040 (5)
C7	0.0241 (6)	0.0215 (6)	0.0347 (7)	−0.0077 (5)	0.0025 (5)	−0.0088 (5)
C8	0.0229 (6)	0.0274 (7)	0.0392 (8)	−0.0073 (5)	0.0025 (5)	−0.0088 (6)
C9	0.0289 (6)	0.0260 (6)	0.0255 (6)	−0.0128 (5)	−0.0024 (5)	−0.0061 (5)
C10	0.0236 (6)	0.0224 (6)	0.0220 (6)	−0.0081 (5)	−0.0026 (5)	−0.0034 (5)
C11	0.0286 (7)	0.0337 (7)	0.0317 (7)	−0.0115 (6)	−0.0113 (5)	0.0038 (6)
C12	0.0452 (8)	0.0378 (8)	0.0246 (7)	−0.0210 (7)	−0.0034 (6)	−0.0016 (6)
Cl1	0.02788 (17)	0.0430 (2)	0.03519 (18)	−0.01831 (14)	−0.00224 (13)	−0.00861 (14)
O1	0.0303 (5)	0.0377 (6)	0.0367 (5)	−0.0128 (4)	0.0007 (4)	−0.0094 (4)
N1	0.0205 (5)	0.0191 (5)	0.0234 (5)	−0.0059 (4)	−0.0013 (4)	−0.0044 (4)
N2	0.0229 (5)	0.0332 (6)	0.0291 (6)	−0.0136 (4)	0.0028 (4)	−0.0101 (5)

C9—C10	1.5176 (17)	C6—H7	0.947
C9—N2	1.4986 (17)	C5—C4	1.3851 (19)
C9—H12	0.966	C5—H6	0.968
C9—H13	0.985	C4—C3	1.3957 (19)
C10—N1	1.4686 (16)	C4—H5	0.965
C10—H14	1.005	C3—C2	1.4070 (17)
C10—H15	0.993	C3—C12	1.5038 (19)
C7—C8	1.5159 (17)	C2—C11	1.5090 (17)
C7—N1	1.4701 (16)	C12—H21	0.975
C7—H9	0.974	C12—H20	0.974
C7—H8	0.991	C12—H19	0.993
C8—N2	1.4900 (18)	C11—H18	0.983
C8—H11	0.995	C11—H16	0.981
C8—H10	0.989	C11—H17	0.981
C1—C6	1.3979 (17)	O1—H1	0.822
C1—C2	1.4060 (17)	O1—H2	0.831
C1—N1	1.4391 (15)	N2—H3	0.900
C6—C5	1.3886 (18)	N2—H4	0.914
C10—C9—N2	109.56 (10)	C4—C5—H6	120.8
C10—C9—H12	111.0	C5—C4—C3	120.72 (12)
N2—C9—H12	108.8	C5—C4—H5	120.5
C10—C9—H13	110.3	C3—C4—H5	118.7
N2—C9—H13	108.5	C4—C3—C2	119.63 (12)
H12—C9—H13	108.6	C4—C3—C12	119.84 (12)
C9—C10—N1	109.41 (10)	C2—C3—C12	120.53 (12)
C9—C10—H14	109.0	C3—C2—C1	119.20 (11)
N1—C10—H14	108.9	C3—C2—C11	119.40 (12)
C9—C10—H15	108.6	C1—C2—C11	121.39 (11)
N1—C10—H15	111.3	C3—C12—H21	109.5
H14—C10—H15	109.6	C3—C12—H20	109.5
C8—C7—N1	110.04 (10)	H21—C12—H20	107.6
C8—C7—H9	108.4	C3—C12—H19	110.4
N1—C7—H9	109.2	H21—C12—H19	109.8
C8—C7—H8	109.4	H20—C12—H19	109.9
N1—C7—H8	110.2	C2—C11—H18	109.7
H9—C7—H8	109.5	C2—C11—H16	110.8
C7—C8—N2	109.88 (11)	H18—C11—H16	109.0
C7—C8—H11	110.1	C2—C11—H17	110.4
N2—C8—H11	107.8	H18—C11—H17	108.5
C7—C8—H10	111.2	H16—C11—H17	108.4
N2—C8—H10	108.0	H1—O1—H2	107.1
H11—C8—H10	109.9	C7—N1—C10	109.62 (10)
C6—C1—C2	120.31 (11)	C7—N1—C1	112.16 (9)
C6—C1—N1	121.24 (11)	C10—N1—C1	115.19 (10)
C2—C1—N1	118.45 (11)	C9—N2—C8	112.04 (10)
C1—C6—C5	119.86 (12)	C9—N2—H3	107.5
C1—C6—H7	119.9	C8—N2—H3	109.3
C5—C6—H7	120.2	C9—N2—H4	108.6
C6—C5—C4	120.27 (12)	C8—N2—H4	110.2
C6—C5—H6	118.9	H3—N2—H4	109.1

D—H···A	D—H	H···A	D···A	D—H···A
N2—H3···Cl1	0.90	2.18	3.069 (1)	169
N2—H4···O1i	0.91	1.86	2.776 (2)	175
O1—H1···Cl1	0.82	2.32	3.120 (1)	165
O1—H2···Cl1ii	0.83	2.31	3.136 (1)	171
C10—H15···Cl1iii	0.99	2.87	3.846 (1)	168
C12—H20···Cl1iv	0.97	2.84	3.779 (3)	161
C12—H19···O1v	0.99	2.73	3.448 (2)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H3⋯Cl1	0.90	2.18	3.069 (1)	169
N2—H4⋯O1i	0.91	1.86	2.776 (2)	175
O1—H1⋯Cl1	0.82	2.32	3.120 (1)	165
O1—H2⋯Cl1ii	0.83	2.31	3.136 (1)	171
C10—H15⋯Cl1iii	0.99	2.87	3.846 (1)	168
C12—H20⋯Cl1iv	0.97	2.84	3.779 (3)	161
C12—H19⋯O1v	0.99	2.73	3.448 (2)	130

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