(4-Chloro-phen-yl)methanaminium chloride hemihydrate.

In the title hydrated salt, C(7)H(9)ClN(+)·Cl(-)·0.5H(2)O, the water O atom lies on a crystallographic twofold axis. In the crystal, the monoprotonated 4-chloro-benzyl-ammonium cation forms N-H⋯Cl and N-H⋯O hydrogen bonds and the water mol-ecule forms O-H⋯Cl hydrogen bonds, generating layers lying parallel to the bc plane.

Related literature

For the properties of benzyl­amines, see: Markwardt et al. (2005 ▶). For a related structure, see: Dhaouadi et al. (2008 ▶).

Experimental

Crystal data

C7H9ClN+·Cl−·0.5H2O

M = 187.06

Monoclinic,

a = 30.462 (2) Å

b = 4.890 (3) Å

c = 11.738 (2) Å

β = 99.97 (3)°

V = 1722.1 (11) Å3

Z = 8

Ag Kα radiation

λ = 0.56085 Å

μ = 0.35 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Enraf–Nonius TurboCAD-4 diffractometer

5908 measured reflections

4207 independent reflections

2217 reflections with I > 2σ(I)

R int = 0.031

2 standard reflections every 120 min intensity decay: 5%

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.130

S = 1.00

4207 reflections

101 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810021100/hb5481sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021100/hb5481Isup2.hkl

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

C7H9ClN+·Cl−·0.5H2O	F(000) = 776
Mr = 187.06	Dx = 1.443 Mg m−3
Monoclinic, C2/c	Ag Kα radiation, λ = 0.56085 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 30.462 (2) Å	θ = 9–11°
b = 4.890 (3) Å	µ = 0.35 mm−1
c = 11.738 (2) Å	T = 293 K
β = 99.97 (3)°	Block, colourless
V = 1722.1 (11) Å3	0.30 × 0.25 × 0.20 mm
Z = 8

Enraf–Nonius TurboCAD-4 diffractometer	Rint = 0.031
Radiation source: fine-focus sealed tube	θmax = 28.0°, θmin = 2.3°
graphite	h = −50→50
non–profiled ω scans	k = 0→8
5908 measured reflections	l = −5→19
4207 independent reflections	2 standard reflections every 120 min
2217 reflections with I > 2σ(I)	intensity decay: 5%

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)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.130	w = 1/[σ2(Fo2) + (0.0585P)2 + 0.2911P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
4207 reflections	Δρmax = 0.34 e Å−3
101 parameters	Δρmin = −0.32 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0080 (12)

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.

	x	y	z	Uiso*/Ueq
Cl1	0.049348 (13)	0.63727 (9)	0.11132 (4)	0.04257 (13)
O	0.0000	0.2285 (4)	0.2500	0.0494 (5)
H1	0.0151 (8)	0.323 (5)	0.210 (2)	0.089 (9)*
C1	0.12851 (4)	0.0280 (3)	0.40289 (14)	0.0313 (3)
C2	0.12629 (5)	0.1317 (3)	0.29253 (14)	0.0364 (3)
H2	0.1048	0.0661	0.2328	0.044*
C3	0.15582 (5)	0.3328 (3)	0.26977 (14)	0.0371 (3)
H3	0.1538	0.4046	0.1957	0.045*
C4	0.18814 (4)	0.4244 (3)	0.35851 (14)	0.0329 (3)
C5	0.19059 (5)	0.3278 (4)	0.46938 (15)	0.0386 (4)
H5	0.2121	0.3947	0.5289	0.046*
C6	0.16065 (5)	0.1293 (4)	0.49129 (14)	0.0380 (3)
H6	0.1621	0.0631	0.5661	0.046*
C7	0.09748 (5)	−0.1977 (3)	0.42512 (18)	0.0399 (4)
H7A	0.0966	−0.3362	0.3656	0.048*
H7B	0.1090	−0.2824	0.4990	0.048*
Cl2	0.225682 (14)	0.66901 (9)	0.32754 (5)	0.04948 (15)
N	0.05166 (4)	−0.0999 (3)	0.42641 (13)	0.0404 (3)
H0A	0.0347	−0.2400	0.4401	0.061*
H0B	0.0406	−0.0261	0.3582	0.061*
H0C	0.0521	0.0251	0.4817	0.061*

	U11	U22	U33	U12	U13	U23
Cl1	0.0390 (2)	0.0365 (2)	0.0527 (3)	0.00140 (16)	0.00925 (17)	0.00195 (19)
O	0.0523 (11)	0.0428 (10)	0.0574 (12)	0.000	0.0215 (9)	0.000
C1	0.0289 (6)	0.0260 (6)	0.0403 (8)	0.0011 (5)	0.0097 (6)	−0.0002 (6)
C2	0.0372 (7)	0.0376 (8)	0.0333 (8)	−0.0070 (6)	0.0033 (6)	−0.0044 (7)
C3	0.0441 (8)	0.0367 (8)	0.0314 (8)	−0.0060 (7)	0.0086 (6)	0.0008 (7)
C4	0.0281 (6)	0.0281 (6)	0.0444 (9)	−0.0017 (5)	0.0117 (6)	−0.0042 (6)
C5	0.0318 (7)	0.0436 (9)	0.0388 (9)	−0.0035 (6)	0.0011 (6)	−0.0064 (7)
C6	0.0388 (7)	0.0407 (8)	0.0342 (8)	0.0015 (7)	0.0057 (6)	0.0049 (7)
C7	0.0384 (7)	0.0263 (7)	0.0577 (11)	0.0010 (6)	0.0153 (7)	0.0043 (7)
Cl2	0.0432 (2)	0.0391 (2)	0.0709 (3)	−0.01276 (17)	0.0229 (2)	−0.0055 (2)
N	0.0339 (6)	0.0355 (7)	0.0529 (9)	−0.0069 (5)	0.0101 (6)	0.0005 (6)

O—H1	0.84 (2)	C5—C6	1.386 (2)
C1—C2	1.382 (2)	C5—H5	0.9300
C1—C6	1.389 (2)	C6—H6	0.9300
C1—C7	1.505 (2)	C7—N	1.4779 (19)
C2—C3	1.389 (2)	C7—H7A	0.9700
C2—H2	0.9300	C7—H7B	0.9700
C3—C4	1.379 (2)	N—H0A	0.8900
C3—H3	0.9300	N—H0B	0.8900
C4—C5	1.374 (2)	N—H0C	0.8900
C4—Cl2	1.7361 (15)
C2—C1—C6	118.89 (14)	C5—C6—C1	120.84 (15)
C2—C1—C7	120.10 (15)	C5—C6—H6	119.6
C6—C1—C7	120.98 (15)	C1—C6—H6	119.6
C1—C2—C3	120.78 (15)	N—C7—C1	112.77 (13)
C1—C2—H2	119.6	N—C7—H7A	109.0
C3—C2—H2	119.6	C1—C7—H7A	109.0
C4—C3—C2	119.10 (15)	N—C7—H7B	109.0
C4—C3—H3	120.5	C1—C7—H7B	109.0
C2—C3—H3	120.5	H7A—C7—H7B	107.8
C5—C4—C3	121.21 (14)	C7—N—H0A	109.5
C5—C4—Cl2	120.36 (12)	C7—N—H0B	109.5
C3—C4—Cl2	118.42 (13)	H0A—N—H0B	109.5
C4—C5—C6	119.14 (14)	C7—N—H0C	109.5
C4—C5—H5	120.4	H0A—N—H0C	109.5
C6—C5—H5	120.4	H0B—N—H0C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···Cl1i	0.89	2.60	3.2930 (19)	136
N—H0A···Cl1ii	0.89	2.78	3.417 (2)	130
N—H0B···O	0.89	2.04	2.866 (2)	155
N—H0C···Cl1iii	0.89	2.26	3.144 (2)	175
O—H1···Cl1	0.85 (3)	2.28 (3)	3.1230 (18)	171 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H0A⋯Cl1i	0.89	2.60	3.2930 (19)	136
N—H0A⋯Cl1ii	0.89	2.78	3.417 (2)	130
N—H0B⋯O	0.89	2.04	2.866 (2)	155
N—H0C⋯Cl1iii	0.89	2.26	3.144 (2)	175
O—H1⋯Cl1	0.85 (3)	2.28 (3)	3.1230 (18)	171 (3)

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