4-Meth-oxy-benzamidinium acetate.

The title compound, C8H11N2O(+)·CH3CO2(-), was synthesized by a reaction between 4-meth-oxy-benzamidine (4-amidino-anisole) and acetic acid. In the cation, the amidinium group forms a dihedral angle of 11.65 (17)° with the mean plane of the benzene ring. The ionic components are associated in the crystal via N-H(+)⋯O(-) hydrogen bonds, resulting in a one-dimensional structure consisting of dimers and catemers and orientated approximately along the c axis.

Related literature

For the biological and pharmacological relevance of benzamidine, see: Powers & Harper (1999 ▶). For structural analysis of proton-transfer adducts containing mol­ecules of biological inter­est, see: Portalone, (2011a ▶); Portalone & Irrera (2011 ▶). For the supra­molecular association in proton-transfer adducts containing benzamidinium cations, see; Portalone (2010 ▶, 2011b ▶, 2012 ▶); Irrera & Portalone (2012a ▶,b ▶); Irrera et al. (2012 ▶). For hydrogen-bond motifs, see Bernstein et al. (1995 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C8H11N2O+·C2H3O2 −

M = 210.23

Monoclinic,

a = 8.7591 (14) Å

b = 6.5478 (8) Å

c = 19.456 (3) Å

β = 102.580 (14)°

V = 1089.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.21 × 0.18 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur S CCD diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.980, T max = 0.986

14433 measured reflections

2365 independent reflections

1834 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.141

S = 1.08

2365 reflections

156 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); 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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812044911/tk5166sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812044911/tk5166Isup2.hkl

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

C8H11N2O+·C2H3O2−	F(000) = 448
Mr = 210.23	Dx = 1.282 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3220 reflections
a = 8.7591 (14) Å	θ = 2.8–28.9°
b = 6.5478 (8) Å	µ = 0.10 mm−1
c = 19.456 (3) Å	T = 298 K
β = 102.580 (14)°	Tablets, colourless
V = 1089.0 (3) Å3	0.21 × 0.18 × 0.15 mm
Z = 4

Oxford Diffraction Xcalibur S CCD diffractometer	2365 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1834 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
Detector resolution: 16.0696 pixels mm-1	θmax = 27.0°, θmin = 3.3°
ω and φ scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −8→8
Tmin = 0.980, Tmax = 0.986	l = −24→24
14433 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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0561P)2 + 0.3698P] where P = (Fo2 + 2Fc2)/3
2365 reflections	(Δ/σ)max < 0.001
156 parameters	Δρmax = 0.21 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
O3	0.2977 (2)	1.0070 (2)	0.35136 (8)	0.0624 (5)
N1	−0.0153 (2)	0.1780 (3)	0.42774 (8)	0.0453 (4)
H1A	−0.074 (3)	0.064 (4)	0.4296 (12)	0.063 (7)*
H1B	0.054 (3)	0.217 (4)	0.4677 (13)	0.063 (7)*
N2	−0.1170 (2)	0.2005 (3)	0.31128 (9)	0.0468 (4)
H2A	−0.175 (3)	0.081 (4)	0.3149 (12)	0.070 (7)*
H2B	−0.133 (3)	0.261 (3)	0.2696 (13)	0.055 (6)*
C1	0.0643 (2)	0.4636 (3)	0.36478 (9)	0.0343 (4)
C2	0.1370 (2)	0.5636 (3)	0.42564 (10)	0.0449 (5)
H2	0.1318	0.5077	0.4690	0.054*
C3	0.2173 (2)	0.7446 (3)	0.42381 (10)	0.0472 (5)
H3	0.2659	0.8088	0.4655	0.057*
C4	0.2248 (2)	0.8294 (3)	0.35969 (10)	0.0429 (5)
C5	0.1539 (3)	0.7298 (4)	0.29855 (10)	0.0584 (6)
H5	0.1594	0.7856	0.2552	0.070*
C6	0.0756 (3)	0.5502 (3)	0.30090 (10)	0.0510 (5)
H6	0.0293	0.4849	0.2591	0.061*
C7	−0.0247 (2)	0.2737 (3)	0.36775 (9)	0.0356 (4)
C8	0.3954 (3)	1.0997 (4)	0.41088 (13)	0.0624 (6)
H8A	0.3323 (10)	1.130 (2)	0.4474 (7)	0.094*
H8B	0.4395 (17)	1.231 (2)	0.3962 (3)	0.094*
H8C	0.4838 (17)	1.0040 (17)	0.4315 (6)	0.094*
O1	−0.20216 (18)	−0.1693 (2)	0.44118 (7)	0.0548 (4)
O2	−0.29092 (18)	−0.1444 (2)	0.32662 (7)	0.0550 (4)
C9	−0.2818 (2)	−0.2339 (3)	0.38404 (9)	0.0390 (4)
C10	−0.3743 (3)	−0.4258 (3)	0.38417 (12)	0.0606 (6)
H10A	−0.3120 (10)	−0.5337 (17)	0.3841 (9)	0.091*
H10B	−0.4519 (17)	−0.4292 (13)	0.3458 (7)	0.091*
H10C	−0.4143 (17)	−0.4291 (12)	0.4226 (7)	0.091*

	U11	U22	U33	U12	U13	U23
O3	0.0827 (11)	0.0586 (9)	0.0449 (9)	−0.0302 (8)	0.0113 (8)	0.0040 (7)
N1	0.0564 (11)	0.0443 (10)	0.0298 (8)	−0.0120 (8)	−0.0020 (7)	0.0052 (7)
N2	0.0613 (11)	0.0439 (10)	0.0293 (9)	−0.0095 (8)	−0.0034 (8)	0.0040 (7)
C1	0.0389 (10)	0.0354 (9)	0.0271 (9)	0.0018 (7)	0.0039 (7)	0.0009 (7)
C2	0.0616 (13)	0.0460 (11)	0.0263 (9)	−0.0063 (9)	0.0076 (8)	0.0021 (8)
C3	0.0616 (13)	0.0474 (11)	0.0302 (10)	−0.0119 (9)	0.0049 (9)	−0.0056 (8)
C4	0.0485 (11)	0.0423 (10)	0.0379 (10)	−0.0043 (8)	0.0092 (8)	0.0012 (8)
C5	0.0798 (16)	0.0647 (14)	0.0292 (10)	−0.0221 (12)	0.0083 (10)	0.0075 (9)
C6	0.0686 (14)	0.0545 (12)	0.0270 (10)	−0.0158 (10)	0.0037 (9)	−0.0019 (8)
C7	0.0411 (10)	0.0358 (9)	0.0279 (9)	0.0021 (7)	0.0030 (7)	0.0007 (7)
C8	0.0673 (15)	0.0587 (14)	0.0587 (14)	−0.0234 (11)	0.0086 (12)	−0.0064 (11)
O1	0.0657 (10)	0.0627 (9)	0.0293 (7)	−0.0192 (7)	−0.0045 (6)	0.0027 (6)
O2	0.0742 (10)	0.0551 (9)	0.0281 (7)	−0.0154 (7)	−0.0053 (7)	0.0019 (6)
C9	0.0376 (10)	0.0436 (10)	0.0330 (10)	−0.0009 (8)	0.0014 (8)	−0.0003 (8)
C10	0.0608 (14)	0.0558 (13)	0.0603 (15)	−0.0123 (11)	0.0023 (12)	0.0026 (11)

O3—C4	1.353 (2)	C3—H3	0.9300
O3—C8	1.418 (3)	C4—C5	1.380 (3)
N1—C7	1.312 (2)	C5—C6	1.367 (3)
N1—H1A	0.91 (3)	C5—H5	0.9300
N1—H1B	0.91 (2)	C6—H6	0.9300
N2—C7	1.306 (2)	C8—H8A	1.0093
N2—H2A	0.94 (3)	C8—H8B	1.0093
N2—H2B	0.88 (2)	C8—H8C	1.0093
C1—C2	1.381 (2)	O1—C9	1.250 (2)
C1—C6	1.389 (3)	O2—C9	1.249 (2)
C1—C7	1.475 (2)	C9—C10	1.495 (3)
C2—C3	1.383 (3)	C10—H10A	0.8930
C2—H2	0.9300	C10—H10B	0.8930
C3—C4	1.380 (3)	C10—H10C	0.8930
C4—O3—C8	119.11 (16)	C5—C6—C1	121.01 (18)
C7—N1—H1A	120.0 (14)	C5—C6—H6	119.5
C7—N1—H1B	121.9 (15)	C1—C6—H6	119.5
H1A—N1—H1B	118 (2)	N2—C7—N1	118.69 (18)
C7—N2—H2A	119.1 (14)	N2—C7—C1	120.84 (16)
C7—N2—H2B	123.6 (14)	N1—C7—C1	120.45 (16)
H2A—N2—H2B	117 (2)	O3—C8—H8A	109.5
C2—C1—C6	117.64 (17)	O3—C8—H8B	109.5
C2—C1—C7	120.99 (16)	H8A—C8—H8B	109.5
C6—C1—C7	121.36 (16)	O3—C8—H8C	109.5
C1—C2—C3	121.77 (17)	H8A—C8—H8C	109.5
C1—C2—H2	119.1	H8B—C8—H8C	109.5
C3—C2—H2	119.1	O2—C9—O1	123.45 (18)
C4—C3—C2	119.52 (17)	O2—C9—C10	117.82 (16)
C4—C3—H3	120.2	O1—C9—C10	118.71 (17)
C2—C3—H3	120.2	C9—C10—H10A	109.5
O3—C4—C5	116.00 (17)	C9—C10—H10B	109.5
O3—C4—C3	124.78 (17)	H10A—C10—H10B	109.5
C5—C4—C3	119.22 (18)	C9—C10—H10C	109.5
C6—C5—C4	120.83 (18)	H10A—C10—H10C	109.5
C6—C5—H5	119.6	H10B—C10—H10C	109.5
C4—C5—H5	119.6
C6—C1—C2—C3	0.6 (3)	C3—C4—C5—C6	0.6 (4)
C7—C1—C2—C3	−178.24 (18)	C4—C5—C6—C1	0.5 (4)
C1—C2—C3—C4	0.4 (3)	C2—C1—C6—C5	−1.1 (3)
C8—O3—C4—C5	−169.3 (2)	C7—C1—C6—C5	177.8 (2)
C8—O3—C4—C3	10.9 (3)	C2—C1—C7—N2	167.00 (19)
C2—C3—C4—O3	178.89 (19)	C6—C1—C7—N2	−11.9 (3)
C2—C3—C4—C5	−1.0 (3)	C2—C1—C7—N1	−11.3 (3)
O3—C4—C5—C6	−179.3 (2)	C6—C1—C7—N1	169.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.91 (3)	1.94 (3)	2.847 (2)	175 (2)
N1—H1B···O1i	0.91 (2)	1.98 (2)	2.832 (2)	155 (2)
N2—H2A···O2	0.94 (3)	1.83 (3)	2.776 (2)	176 (2)
N2—H2B···O2ii	0.88 (2)	1.95 (2)	2.817 (2)	168 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.91 (3)	1.94 (3)	2.847 (2)	175 (2)
N1—H1B⋯O1i	0.91 (2)	1.98 (2)	2.832 (2)	155 (2)
N2—H2A⋯O2	0.94 (3)	1.83 (3)	2.776 (2)	176 (2)
N2—H2B⋯O2ii	0.88 (2)	1.95 (2)	2.817 (2)	168 (2)

Symmetry codes: (i) ; (ii) .