4-Meth-oxy-benzamidinium chloride monohydrate.

In the cation of the title compound, C(8)H(11)N(2)O(+)·Cl(-)·H(2)O, the C-N bonds of the amidinium group are identical within experiemental error [1.305 (2) and 1.304 (2) Å], and its plane forms a dihedral angle of 25.83 (8)° with the phenyl ring. The ionic components are associated in the crystal into polymeric hydrogen-bonded supra-molecular tapes stabilized by N-H(+)⋯Cl(-) and N-H(+)⋯Ow inter-molecular hydrogen bonds, and by Ow-H⋯Cl(-) inter-actions.

Related literature

For the biological and pharmacological relevance of benzamid­ine, see: Marquart et al. (1983 ▶); Sprang et al. (1987 ▶); Bode et al. (1990 ▶); Powers & Harper (1999 ▶); Grzesiak et al. (2000 ▶). For structural analysis of proton-transfer adducts containing mol­ecules of biological inter­est, see: Portalone (2011a ▶); n class="Chemical">Portalone & Irrera (2011 ▶). For the supra­molecular association in proton-transfer adducts containing benzamidinium cations, see; Portalone (2010 ▶, 2011b ▶, 2012 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C8H11N2O+·Cl−·H2O

M = 204.65

Monoclinic,

a = 11.3029 (7) Å

b = 9.3142 (5) Å

c = 9.9983 (6) Å

β = 99.820 (6)°

V = 1037.17 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 298 K

0.30 × 0.27 × 0.25 mm

Data collection

Oxford Diffraction Xcalibur S CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 ▶) T min = 0.905, T max = 0.968

7158 measured reflections

2989 independent reflections

1947 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.113

S = 0.97

2989 reflections

144 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis n class="Disease">CCD; data reduction: CrysAlis 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 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812041219/qm2085sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812041219/qm2085Isup2.hkl

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

C8H11N2O+·Cl−·H2O	F(000) = 432
Mr = 204.65	Dx = 1.311 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 3182 reflections
a = 11.3029 (7) Å	θ = 2.8–32.2°
b = 9.3142 (5) Å	µ = 0.34 mm−1
c = 9.9983 (6) Å	T = 298 K
β = 99.820 (6)°	Tablets, colourless
V = 1037.17 (11) Å3	0.30 × 0.27 × 0.25 mm
Z = 4

Oxford Diffraction Xcalibur S CCD diffractometer	2989 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1947 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
Detector resolution: 16.0696 pixels mm-1	θmax = 30.0°, θmin = 2.9°
ω and φ scans	h = −15→13
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −13→13
Tmin = 0.905, Tmax = 0.968	l = −14→14
7158 measured reflections

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ2(Fo2) + (0.0667P)2] where P = (Fo2 + 2Fc2)/3
2989 reflections	(Δ/σ)max < 0.001
144 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.59874 (3)	0.29686 (5)	0.19860 (4)	0.06143 (17)
O1	0.02187 (9)	0.02872 (12)	0.72746 (11)	0.0585 (3)
N1	0.37553 (14)	0.36637 (18)	0.40096 (17)	0.0577 (4)
H1A	0.4215 (18)	0.391 (3)	0.351 (2)	0.087 (7)*
H1B	0.3457 (16)	0.424 (2)	0.4357 (19)	0.070 (7)*
N2	0.40806 (13)	0.1372 (2)	0.34687 (16)	0.0609 (4)
H2A	0.4716 (18)	0.167 (2)	0.300 (2)	0.082 (6)*
H2B	0.3898 (16)	0.052 (3)	0.3475 (19)	0.077 (7)*
C1	0.26509 (11)	0.18152 (15)	0.49586 (13)	0.0400 (3)
C2	0.17291 (12)	0.26955 (17)	0.52024 (16)	0.0499 (4)
H2	0.1669	0.3620	0.4847	0.060*
C3	0.08913 (12)	0.22277 (17)	0.59666 (16)	0.0497 (4)
H3	0.0273	0.2832	0.6120	0.060*
C4	0.09816 (11)	0.08562 (16)	0.64994 (14)	0.0425 (3)
C5	0.19078 (12)	−0.00346 (17)	0.62752 (15)	0.0489 (4)
H5	0.1974	−0.0953	0.6645	0.059*
C6	0.27322 (12)	0.04365 (16)	0.55054 (14)	0.0460 (3)
H6	0.3348	−0.0171	0.5350	0.055*
C7	0.35238 (11)	0.22994 (17)	0.41160 (14)	0.0460 (4)
C8	−0.07725 (14)	0.1140 (2)	0.75071 (19)	0.0684 (5)
H8A	−0.0482 (3)	0.2006 (11)	0.7969 (13)	0.103*
H8B	−0.1241 (9)	0.0612 (8)	0.8055 (12)	0.103*
H8C	−0.1263 (8)	0.1375 (12)	0.6654 (9)	0.103*
O2W	0.27853 (14)	0.61140 (16)	0.50438 (18)	0.0783 (4)
HWA	0.319 (3)	0.631 (4)	0.579 (3)	0.155 (14)*
HWB	0.3124 (17)	0.667 (2)	0.452 (2)	0.077 (6)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0604 (3)	0.0699 (3)	0.0594 (3)	−0.00364 (19)	0.02536 (19)	0.0085 (2)
O1	0.0518 (6)	0.0581 (7)	0.0737 (7)	0.0039 (5)	0.0337 (5)	0.0110 (6)
N1	0.0595 (8)	0.0550 (9)	0.0642 (9)	−0.0047 (7)	0.0267 (7)	0.0125 (8)
N2	0.0583 (8)	0.0688 (11)	0.0628 (9)	−0.0090 (8)	0.0311 (7)	−0.0027 (8)
C1	0.0358 (6)	0.0472 (8)	0.0373 (7)	−0.0039 (6)	0.0072 (5)	0.0001 (6)
C2	0.0510 (8)	0.0403 (8)	0.0604 (9)	0.0036 (6)	0.0156 (7)	0.0089 (7)
C3	0.0437 (7)	0.0463 (9)	0.0629 (9)	0.0077 (6)	0.0195 (6)	0.0020 (7)
C4	0.0384 (6)	0.0464 (8)	0.0443 (7)	−0.0017 (6)	0.0117 (5)	0.0002 (6)
C5	0.0496 (7)	0.0421 (8)	0.0584 (9)	0.0047 (7)	0.0191 (6)	0.0082 (7)
C6	0.0420 (7)	0.0449 (8)	0.0541 (8)	0.0078 (6)	0.0167 (6)	0.0032 (7)
C7	0.0405 (7)	0.0559 (10)	0.0420 (7)	−0.0040 (6)	0.0084 (6)	0.0045 (7)
C8	0.0503 (8)	0.0838 (13)	0.0787 (12)	0.0101 (8)	0.0329 (8)	0.0039 (10)
O2W	0.1035 (11)	0.0605 (8)	0.0747 (10)	−0.0175 (8)	0.0258 (9)	0.0015 (7)

O1—C4	1.3613 (16)	C2—H2	0.9300
O1—C8	1.4243 (18)	C3—C4	1.381 (2)
N1—C7	1.305 (2)	C3—H3	0.9300
N1—H1A	0.81 (2)	C4—C5	1.3837 (19)
N1—H1B	0.75 (2)	C5—C6	1.3776 (19)
N2—C7	1.304 (2)	C5—H5	0.9300
N2—H2A	0.96 (2)	C6—H6	0.9300
N2—H2B	0.82 (2)	C8—H8A	0.9596
C1—C2	1.3798 (19)	C8—H8B	0.9596
C1—C6	1.3926 (19)	C8—H8C	0.9596
C1—C7	1.4731 (18)	O2W—HWA	0.82 (3)
C2—C3	1.385 (2)	O2W—HWB	0.87 (2)
C4—O1—C8	117.92 (13)	C3—C4—C5	120.02 (12)
C7—N1—H1A	119.0 (17)	C6—C5—C4	120.14 (14)
C7—N1—H1B	123.3 (15)	C6—C5—H5	119.9
H1A—N1—H1B	118 (2)	C4—C5—H5	119.9
C7—N2—H2A	120.7 (11)	C5—C6—C1	120.49 (12)
C7—N2—H2B	119.6 (14)	C5—C6—H6	119.8
H2A—N2—H2B	119.7 (18)	C1—C6—H6	119.8
C2—C1—C6	118.68 (12)	N2—C7—N1	118.95 (15)
C2—C1—C7	121.24 (13)	N2—C7—C1	120.53 (15)
C6—C1—C7	120.07 (12)	N1—C7—C1	120.52 (15)
C1—C2—C3	121.24 (14)	O1—C8—H8A	109.5
C1—C2—H2	119.4	O1—C8—H8B	109.5
C3—C2—H2	119.4	H8A—C8—H8B	109.5
C4—C3—C2	119.43 (13)	O1—C8—H8C	109.5
C4—C3—H3	120.3	H8A—C8—H8C	109.5
C2—C3—H3	120.3	H8B—C8—H8C	109.5
O1—C4—C3	124.57 (12)	HWA—O2W—HWB	100 (3)
O1—C4—C5	115.41 (13)
C6—C1—C2—C3	−0.4 (2)	C3—C4—C5—C6	−0.9 (2)
C7—C1—C2—C3	178.39 (14)	C4—C5—C6—C1	0.7 (2)
C1—C2—C3—C4	0.2 (2)	C2—C1—C6—C5	−0.1 (2)
C8—O1—C4—C3	2.8 (2)	C7—C1—C6—C5	−178.88 (14)
C8—O1—C4—C5	−178.22 (14)	C2—C1—C7—N2	−153.81 (15)
C2—C3—C4—O1	179.33 (14)	C6—C1—C7—N2	25.0 (2)
C2—C3—C4—C5	0.4 (2)	C2—C1—C7—N1	26.4 (2)
O1—C4—C5—C6	−179.90 (14)	C6—C1—C7—N1	−154.78 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1	0.81 (2)	2.85 (2)	3.5523 (18)	145 (2)
N1—H1B···O2W	0.75 (2)	2.06 (2)	2.805 (2)	168 (2)
N2—H2A···Cl1	0.96 (2)	2.25 (2)	3.1850 (16)	164.4 (16)
N2—H2B···Cl1i	0.82 (2)	2.43 (2)	3.201 (2)	157.5 (18)
O2W—HWA···Cl1ii	0.82 (3)	2.36 (3)	3.1731 (18)	170 (3)
O2W—HWB···Cl1iii	0.87 (2)	2.29 (2)	3.1603 (17)	174.8 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl1	0.81 (2)	2.85 (2)	3.5523 (18)	145 (2)
N1—H1B⋯O2W	0.75 (2)	2.06 (2)	2.805 (2)	168 (2)
N2—H2A⋯Cl1	0.96 (2)	2.25 (2)	3.1850 (16)	164.4 (16)
N2—H2B⋯Cl1i	0.82 (2)	2.43 (2)	3.201 (2)	157.5 (18)
O2W—HWA⋯Cl1ii	0.82 (3)	2.36 (3)	3.1731 (18)	170 (3)
O2W—HWB⋯Cl1iii	0.87 (2)	2.29 (2)	3.1603 (17)	174.8 (19)

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