4-Meth-oxy-benzamidinium nitrate.

The title salt, C8H11N2O(+)·NO3(-), was synthesized by a reaction between 4-meth-oxy-benzamidine (4-amidino-anisole) and nitric acid. The asymmetric unit comprises a non-planar 4-meth-oxy-benzamidinium cation and a nitrate anion. In the cation, the amidinium group has two similar C-N bond lengths [1.302 (3) and 1.313 (3) Å] and its plane forms a dihedral angle of 32.66 (5)° with the mean plane of the benzene ring. The nitrate-amidinium ion pair is not planar, as the dihedral angle between the planes defined by the CN2(+) and NO3(-) units is 19.28 (6)°. The ionic components are associated in the crystal via N-H⋯O hydrogen bonds, resulting in a three-dimensional network.

Related literature

For the biological and pharmacological relevance of benzamidine, see: Powers & Harper (1999 ▶); Grzesiak et al. (2000 ▶). 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 (2012 ▶); Irrera et al. (2012 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C8H11N2O+·NO3 −

M = 213.20

Orthorhombic,

a = 7.1049 (7) Å

b = 10.3558 (8) Å

c = 13.4325 (9) Å

V = 988.32 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 298 K

0.20 × 0.10 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur S CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 ▶) T min = 0.977, T max = 0.991

6206 measured reflections

1253 independent reflections

989 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.083

S = 0.98

1253 reflections

154 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.12 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis 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 (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812045874/fi2127sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812045874/fi2127Isup2.hkl

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

C8H11N2O+·NO3−	F(000) = 448
Mr = 213.20	Dx = 1.433 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2927 reflections
a = 7.1049 (7) Å	θ = 3.0–29.0°
b = 10.3558 (8) Å	µ = 0.12 mm−1
c = 13.4325 (9) Å	T = 298 K
V = 988.32 (14) Å3	Tablets, colourless
Z = 4	0.20 × 0.10 × 0.08 mm

Oxford Diffraction Xcalibur S CCD diffractometer	1253 independent reflections
Radiation source: Enhance (Mo) X-ray Source	989 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 16.0696 pixels mm-1	θmax = 27.0°, θmin = 3.0°
ω and φ scans	h = −8→8
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −13→12
Tmin = 0.977, Tmax = 0.991	l = −17→17
6206 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ2(Fo2) + (0.0527P)2 + 0.0001P] where P = (Fo2 + 2Fc2)/3
1253 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.20 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
O4	0.3500 (3)	0.10530 (16)	0.33730 (12)	0.0565 (5)
N1	0.3218 (3)	0.3966 (2)	−0.07851 (16)	0.0441 (5)
H1A	0.325 (3)	0.426 (2)	−0.1390 (18)	0.041 (6)*
H1B	0.268 (3)	0.448 (2)	−0.0308 (18)	0.044 (7)*
N2	0.4153 (3)	0.1984 (2)	−0.12938 (16)	0.0454 (5)
H2A	0.408 (3)	0.222 (3)	−0.1914 (18)	0.046 (7)*
H2B	0.463 (3)	0.127 (3)	−0.1138 (17)	0.045 (8)*
C1	0.3682 (3)	0.2331 (2)	0.04594 (15)	0.0359 (5)
C2	0.4110 (3)	0.3182 (2)	0.12224 (14)	0.0377 (5)
H2	0.4426	0.4032	0.1072	0.045*
C3	0.4073 (3)	0.2785 (2)	0.22025 (16)	0.0419 (5)
H3	0.4372	0.3363	0.2708	0.050*
C4	0.3588 (3)	0.1520 (2)	0.24330 (16)	0.0397 (5)
C5	0.3158 (3)	0.0660 (2)	0.16755 (17)	0.0432 (5)
H5	0.2832	−0.0188	0.1827	0.052*
C6	0.3215 (3)	0.1061 (2)	0.07021 (17)	0.0401 (5)
H6	0.2937	0.0478	0.0197	0.048*
C7	0.3686 (3)	0.2769 (2)	−0.05791 (15)	0.0347 (5)
C8	0.3767 (4)	0.1947 (3)	0.41712 (18)	0.0639 (8)
H8A	0.498 (3)	0.2338 (16)	0.4114 (9)	0.096*
H8B	0.368 (3)	0.1501 (8)	0.4793 (11)	0.096*
H8C	0.282 (2)	0.2602 (17)	0.4141 (9)	0.096*
N3	0.3829 (3)	0.3901 (2)	−0.35182 (15)	0.0471 (5)
O1	0.3880 (3)	0.46641 (18)	−0.28077 (14)	0.0669 (5)
O2	0.3696 (3)	0.27255 (18)	−0.33771 (13)	0.0735 (6)
O3	0.3962 (3)	0.43439 (17)	−0.43752 (12)	0.0611 (5)

	U11	U22	U33	U12	U13	U23
O4	0.0789 (12)	0.0439 (10)	0.0466 (9)	−0.0041 (10)	0.0002 (8)	0.0075 (9)
N1	0.0525 (12)	0.0399 (12)	0.0401 (11)	0.0049 (10)	0.0049 (9)	0.0023 (10)
N2	0.0481 (12)	0.0456 (14)	0.0425 (12)	0.0050 (11)	0.0003 (9)	−0.0013 (10)
C1	0.0272 (10)	0.0357 (12)	0.0448 (11)	0.0026 (9)	0.0010 (9)	−0.0008 (10)
C2	0.0386 (12)	0.0279 (12)	0.0466 (12)	−0.0024 (9)	−0.0005 (9)	−0.0001 (10)
C3	0.0477 (13)	0.0346 (11)	0.0433 (11)	−0.0016 (11)	−0.0055 (10)	−0.0071 (11)
C4	0.0403 (12)	0.0363 (12)	0.0426 (11)	0.0034 (10)	0.0002 (9)	0.0048 (11)
C5	0.0460 (13)	0.0297 (12)	0.0537 (13)	−0.0028 (11)	0.0043 (11)	0.0007 (11)
C6	0.0370 (11)	0.0345 (12)	0.0488 (12)	−0.0006 (10)	−0.0001 (10)	−0.0055 (11)
C7	0.0264 (10)	0.0359 (12)	0.0416 (11)	0.0001 (9)	0.0020 (9)	−0.0032 (11)
C8	0.0867 (19)	0.0635 (18)	0.0415 (12)	−0.0123 (17)	−0.0007 (13)	0.0001 (13)
N3	0.0480 (11)	0.0489 (12)	0.0446 (10)	0.0027 (10)	−0.0002 (10)	0.0090 (11)
O1	0.0978 (14)	0.0531 (11)	0.0498 (9)	0.0019 (11)	0.0058 (10)	0.0028 (9)
O2	0.1182 (17)	0.0438 (11)	0.0586 (10)	−0.0156 (12)	−0.0060 (12)	0.0124 (9)
O3	0.0836 (12)	0.0565 (11)	0.0434 (9)	0.0070 (10)	0.0062 (9)	0.0164 (9)

O4—C4	1.354 (3)	C3—C4	1.390 (3)
O4—C8	1.429 (3)	C3—H3	0.9300
N1—C7	1.313 (3)	C4—C5	1.387 (3)
N1—H1A	0.87 (2)	C5—C6	1.373 (3)
N1—H1B	0.91 (2)	C5—H5	0.9300
N2—C7	1.302 (3)	C6—H6	0.9300
N2—H2A	0.87 (2)	C8—H8A	0.9572
N2—H2B	0.84 (3)	C8—H8B	0.9572
C1—C2	1.386 (3)	C8—H8C	0.9572
C1—C6	1.395 (3)	N3—O2	1.235 (3)
C1—C7	1.467 (3)	N3—O1	1.240 (3)
C2—C3	1.379 (3)	N3—O3	1.243 (2)
C2—H2	0.9300
C4—O4—C8	117.53 (18)	C6—C5—C4	119.9 (2)
C7—N1—H1A	121.4 (16)	C6—C5—H5	120.1
C7—N1—H1B	120.3 (14)	C4—C5—H5	120.1
H1A—N1—H1B	118 (2)	C5—C6—C1	121.0 (2)
C7—N2—H2A	120.8 (17)	C5—C6—H6	119.5
C7—N2—H2B	118.0 (16)	C1—C6—H6	119.5
H2A—N2—H2B	121 (2)	N2—C7—N1	120.0 (2)
C2—C1—C6	118.62 (19)	N2—C7—C1	120.6 (2)
C2—C1—C7	120.41 (18)	N1—C7—C1	119.49 (19)
C6—C1—C7	120.95 (19)	O4—C8—H8A	109.5
C3—C2—C1	120.8 (2)	O4—C8—H8B	109.5
C3—C2—H2	119.6	H8A—C8—H8B	109.5
C1—C2—H2	119.6	O4—C8—H8C	109.5
C2—C3—C4	119.9 (2)	H8A—C8—H8C	109.5
C2—C3—H3	120.1	H8B—C8—H8C	109.5
C4—C3—H3	120.1	O2—N3—O1	120.82 (19)
O4—C4—C5	116.40 (19)	O2—N3—O3	120.8 (2)
O4—C4—C3	123.8 (2)	O1—N3—O3	118.4 (2)
C5—C4—C3	119.8 (2)
C6—C1—C2—C3	−0.1 (3)	C3—C4—C5—C6	0.1 (3)
C7—C1—C2—C3	178.67 (18)	C4—C5—C6—C1	−0.6 (3)
C1—C2—C3—C4	−0.5 (3)	C2—C1—C6—C5	0.6 (3)
C8—O4—C4—C5	−174.4 (2)	C7—C1—C6—C5	−178.10 (19)
C8—O4—C4—C3	5.5 (3)	C2—C1—C7—N2	148.0 (2)
C2—C3—C4—O4	−179.38 (19)	C6—C1—C7—N2	−33.3 (3)
C2—C3—C4—C5	0.5 (3)	C2—C1—C7—N1	−31.7 (3)
O4—C4—C5—C6	179.9 (2)	C6—C1—C7—N1	147.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.87 (2)	2.00 (2)	2.850 (3)	166 (2)
N1—H1B···O3i	0.91 (2)	2.10 (2)	3.008 (3)	170 (2)
N2—H2A···O2	0.87 (2)	2.05 (2)	2.920 (3)	175 (2)
N2—H2B···O1ii	0.84 (3)	2.43 (3)	3.030 (3)	129 (2)
N2—H2B···O3ii	0.84 (3)	2.33 (3)	3.174 (3)	177 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.87 (2)	2.00 (2)	2.850 (3)	166 (2)
N1—H1B⋯O3i	0.91 (2)	2.10 (2)	3.008 (3)	170 (2)
N2—H2A⋯O2	0.87 (2)	2.05 (2)	2.920 (3)	175 (2)
N2—H2B⋯O1ii	0.84 (3)	2.43 (3)	3.030 (3)	129 (2)
N2—H2B⋯O3ii	0.84 (3)	2.33 (3)	3.174 (3)	177 (2)

Symmetry codes: (i) ; (ii) .