4-Meth-oxy-anilinium nitrate.

The title compound, C(7)H(10)NO(+)·NO(3) (-), crystallized with two p-ansidinium cations and two nitrate anions in the asymmetric unit. As well as Columbic and van der Waals forces, moleucles inter-act via multiple bifurcated N-H⋯O hydrogen bonds that help consolidate the crystal packing, resulting in a three-dimensional network.

Related literature

For background to anisidine, see: Li et al. (2001 ▶). For applications of nitrates, see: Kapoor et al. (2008 ▶). Association of both entities could lead to new molecular salts with inter­esting physical and chemical properties, see: Wilkes et al. (1985 ▶). For related structures, see: Ben Amor et al. (1995 ▶); Liu et al. (2011 ▶).

Experimental

Crystal data

C7H10NO+·NO3 −

M = 186.17

Monoclinic,

a = 14.724 (2) Å

b = 7.304 (3) Å

c = 17.509 (2) Å

β = 112.84 (2)°

V = 1735.3 (8) Å3

Z = 8

Ag Kα radiation

λ = 0.56085 Å

μ = 0.07 mm−1

T = 293 K

0.35 × 0.25 × 0.20 mm

Data collection

Enraf–Nonius TurboCAD-4 diffractometer

12462 measured reflections

8244 independent reflections

2756 reflections with I > 2σ(I)

R int = 0.033

2 standard reflections every 120 min intensity decay: 5%

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.219

S = 0.93

8244 reflections

235 parameters

H-atom parameters not refined

Δρmax = 0.53 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811031862/fl2352sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031862/fl2352Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811031862/fl2352Isup3.cml

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

C7H10NO+·NO3−	F(000) = 784
Mr = 186.17	Dx = 1.425 Mg m−3
Monoclinic, P21/n	Ag Kα radiation, λ = 0.56085 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 14.724 (2) Å	θ = 9–11°
b = 7.304 (3) Å	µ = 0.07 mm−1
c = 17.509 (2) Å	T = 293 K
β = 112.84 (2)°	Block, brown
V = 1735.3 (8) Å3	0.35 × 0.25 × 0.20 mm
Z = 8

Enraf–Nonius TurboCAD-4 diffractometer	Rint = 0.033
Radiation source: fine-focus sealed tube	θmax = 28.0°, θmin = 2.4°
graphite	h = −24→23
non–profiled ω scans	k = −3→12
12462 measured reflections	l = −2→29
8244 independent reflections	2 standard reflections every 120 min
2756 reflections with I > 2σ(I)	intensity decay: 5%

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.219	H-atom parameters not refined
S = 0.93	w = 1/[σ2(Fo2) + (0.0981P)2] where P = (Fo2 + 2Fc2)/3
8244 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.53 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
N4	0.45826 (13)	−0.1031 (3)	0.55952 (10)	0.0482 (4)
O7	0.42497 (16)	−0.2382 (2)	0.51123 (13)	0.0797 (6)
O8	0.53055 (17)	−0.0919 (6)	0.61993 (13)	0.1391 (13)
C8	0.32040 (12)	0.3581 (2)	0.13224 (11)	0.0384 (4)
N2	0.23464 (11)	0.4351 (2)	0.14327 (10)	0.0439 (4)
H2A	0.2350	0.4003	0.1921	0.066*
H2B	0.1798	0.3952	0.1030	0.066*
H2C	0.2369	0.5567	0.1414	0.066*
O2	0.56519 (10)	0.1375 (2)	0.10671 (9)	0.0554 (4)
C9	0.38580 (13)	0.2496 (3)	0.19357 (12)	0.0425 (4)
H9	0.3755	0.2252	0.2418	0.051*
C10	0.46634 (14)	0.1778 (3)	0.18263 (12)	0.0460 (4)
H10	0.5105	0.1038	0.2235	0.055*
C11	0.48208 (13)	0.2150 (3)	0.11122 (11)	0.0411 (4)
C12	0.41615 (15)	0.3222 (3)	0.04975 (12)	0.0518 (5)
H12	0.4260	0.3461	0.0014	0.062*
C13	0.33478 (15)	0.3940 (3)	0.06103 (12)	0.0503 (5)
H13	0.2900	0.4667	0.0200	0.060*
C14	0.58718 (17)	0.1818 (4)	0.03694 (15)	0.0594 (6)
H14A	0.6462	0.1195	0.0409	0.089*
H14B	0.5966	0.3116	0.0354	0.089*
H14C	0.5336	0.1444	−0.0127	0.089*
O1	0.67037 (11)	0.5777 (2)	0.15815 (8)	0.0509 (4)
C1	0.56621 (13)	0.5870 (2)	0.34540 (11)	0.0381 (4)
C4	0.63880 (13)	0.5719 (3)	0.22190 (11)	0.0396 (4)
C5	0.68716 (14)	0.4806 (3)	0.29573 (12)	0.0422 (4)
H5	0.7438	0.4135	0.3038	0.051*
N1	0.53081 (12)	0.6024 (3)	0.41235 (11)	0.0482 (4)
H1A	0.4758	0.6687	0.3952	0.072*
H1B	0.5766	0.6567	0.4558	0.072*
H1C	0.5185	0.4912	0.4268	0.072*
C2	0.51623 (14)	0.6757 (3)	0.27082 (12)	0.0459 (5)
H2	0.4588	0.7405	0.2625	0.055*
C6	0.65044 (14)	0.4896 (3)	0.35843 (12)	0.0426 (4)
H6	0.6831	0.4298	0.4086	0.051*
C3	0.55199 (14)	0.6674 (3)	0.20970 (12)	0.0467 (5)
H3	0.5182	0.7258	0.1594	0.056*
C7	0.76321 (18)	0.4981 (4)	0.17243 (15)	0.0588 (6)
H7A	0.7774	0.5105	0.1236	0.088*
H7B	0.7619	0.3706	0.1854	0.088*
H7C	0.8133	0.5591	0.2180	0.088*
N3	0.21447 (12)	0.9114 (2)	0.14231 (11)	0.0462 (4)
O3	0.27158 (11)	0.8115 (2)	0.19742 (10)	0.0577 (4)
O4	0.17418 (11)	1.0419 (2)	0.16528 (12)	0.0642 (5)
O5	0.19753 (18)	0.8822 (3)	0.07051 (12)	0.0925 (7)
O6	0.40423 (13)	0.0358 (3)	0.53394 (14)	0.0787 (5)

	U11	U22	U33	U12	U13	U23
N4	0.0599 (10)	0.0482 (10)	0.0424 (9)	0.0005 (9)	0.0262 (8)	0.0083 (8)
O7	0.1130 (15)	0.0479 (10)	0.0942 (14)	−0.0030 (10)	0.0575 (12)	−0.0063 (10)
O8	0.0827 (14)	0.259 (4)	0.0518 (11)	0.0282 (18)	0.0007 (11)	0.0389 (16)
C8	0.0372 (8)	0.0337 (9)	0.0392 (9)	−0.0009 (7)	0.0092 (7)	−0.0012 (7)
N2	0.0417 (8)	0.0402 (9)	0.0448 (8)	0.0024 (7)	0.0112 (7)	0.0001 (7)
O2	0.0528 (8)	0.0581 (10)	0.0563 (9)	0.0137 (7)	0.0223 (7)	0.0056 (7)
C9	0.0422 (9)	0.0421 (10)	0.0370 (9)	−0.0007 (8)	0.0085 (7)	0.0054 (8)
C10	0.0465 (10)	0.0422 (10)	0.0438 (10)	0.0081 (8)	0.0116 (8)	0.0084 (9)
C11	0.0403 (9)	0.0370 (10)	0.0427 (9)	0.0024 (7)	0.0124 (8)	0.0001 (8)
C12	0.0546 (11)	0.0610 (13)	0.0405 (10)	0.0101 (10)	0.0191 (9)	0.0117 (10)
C13	0.0478 (10)	0.0547 (12)	0.0419 (10)	0.0105 (9)	0.0104 (8)	0.0142 (9)
C14	0.0585 (12)	0.0624 (14)	0.0642 (13)	0.0047 (11)	0.0312 (11)	−0.0008 (12)
O1	0.0584 (8)	0.0552 (9)	0.0418 (7)	0.0062 (7)	0.0221 (6)	0.0036 (6)
C1	0.0399 (8)	0.0334 (9)	0.0393 (8)	−0.0047 (7)	0.0136 (7)	−0.0037 (7)
C4	0.0445 (9)	0.0329 (9)	0.0389 (9)	−0.0022 (7)	0.0134 (7)	−0.0021 (7)
C5	0.0430 (9)	0.0385 (10)	0.0444 (10)	0.0074 (8)	0.0161 (8)	0.0035 (8)
N1	0.0446 (8)	0.0523 (10)	0.0484 (9)	−0.0010 (7)	0.0189 (7)	−0.0013 (8)
C2	0.0388 (9)	0.0430 (10)	0.0501 (10)	0.0058 (8)	0.0107 (8)	0.0016 (9)
C6	0.0457 (9)	0.0372 (9)	0.0411 (9)	0.0049 (8)	0.0125 (8)	0.0055 (8)
C3	0.0475 (10)	0.0457 (11)	0.0400 (9)	0.0037 (9)	0.0095 (8)	0.0046 (8)
C7	0.0598 (12)	0.0687 (15)	0.0520 (12)	0.0045 (11)	0.0261 (10)	−0.0026 (11)
N3	0.0418 (8)	0.0362 (8)	0.0506 (9)	−0.0026 (7)	0.0070 (7)	0.0007 (7)
O3	0.0564 (8)	0.0490 (8)	0.0568 (9)	0.0122 (7)	0.0100 (7)	0.0069 (7)
O4	0.0537 (8)	0.0401 (8)	0.0936 (12)	0.0076 (7)	0.0230 (8)	−0.0016 (8)
O5	0.1142 (16)	0.0904 (15)	0.0516 (10)	−0.0027 (13)	0.0089 (10)	−0.0085 (10)
O6	0.0653 (10)	0.0539 (10)	0.1067 (14)	0.0002 (8)	0.0223 (10)	−0.0067 (10)

N4—O8	1.177 (3)	O1—C4	1.366 (2)
N4—O6	1.259 (3)	O1—C7	1.416 (3)
N4—O7	1.268 (2)	C1—C6	1.370 (3)
C8—C13	1.369 (3)	C1—C2	1.386 (3)
C8—C9	1.381 (2)	C1—N1	1.460 (3)
C8—N2	1.462 (2)	C4—C5	1.381 (3)
N2—H2A	0.8900	C4—C3	1.398 (3)
N2—H2B	0.8900	C5—C6	1.401 (3)
N2—H2C	0.8900	C5—H5	0.9300
O2—C11	1.378 (2)	N1—H1A	0.8900
O2—C14	1.417 (3)	N1—H1B	0.8900
C9—C10	1.376 (3)	N1—H1C	0.8900
C9—H9	0.9300	C2—C3	1.365 (3)
C10—C11	1.384 (3)	C2—H2	0.9300
C10—H10	0.9300	C6—H6	0.9300
C11—C12	1.379 (3)	C3—H3	0.9300
C12—C13	1.390 (3)	C7—H7A	0.9600
C12—H12	0.9300	C7—H7B	0.9600
C13—H13	0.9300	C7—H7C	0.9600
C14—H14A	0.9600	N3—O5	1.202 (3)
C14—H14B	0.9600	N3—O3	1.241 (2)
C14—H14C	0.9600	N3—O4	1.268 (2)
O8—N4—O6	119.3 (3)	C4—O1—C7	117.01 (16)
O8—N4—O7	129.4 (3)	C6—C1—C2	121.00 (18)
O6—N4—O7	111.25 (18)	C6—C1—N1	119.25 (16)
C13—C8—C9	120.71 (18)	C2—C1—N1	119.72 (17)
C13—C8—N2	119.57 (16)	O1—C4—C5	124.37 (17)
C9—C8—N2	119.72 (17)	O1—C4—C3	116.13 (17)
C8—N2—H2A	109.5	C5—C4—C3	119.50 (18)
C8—N2—H2B	109.5	C4—C5—C6	119.69 (17)
H2A—N2—H2B	109.5	C4—C5—H5	120.2
C8—N2—H2C	109.5	C6—C5—H5	120.2
H2A—N2—H2C	109.5	C1—N1—H1A	109.5
H2B—N2—H2C	109.5	C1—N1—H1B	109.5
C11—O2—C14	117.42 (16)	H1A—N1—H1B	109.5
C10—C9—C8	119.27 (18)	C1—N1—H1C	109.5
C10—C9—H9	120.4	H1A—N1—H1C	109.5
C8—C9—H9	120.4	H1B—N1—H1C	109.5
C9—C10—C11	120.42 (17)	C3—C2—C1	119.49 (17)
C9—C10—H10	119.8	C3—C2—H2	120.3
C11—C10—H10	119.8	C1—C2—H2	120.3
O2—C11—C12	124.06 (18)	C1—C6—C5	119.58 (17)
O2—C11—C10	115.76 (17)	C1—C6—H6	120.2
C12—C11—C10	120.17 (18)	C5—C6—H6	120.2
C11—C12—C13	119.17 (18)	C2—C3—C4	120.71 (18)
C11—C12—H12	120.4	C2—C3—H3	119.6
C13—C12—H12	120.4	C4—C3—H3	119.6
C8—C13—C12	120.25 (18)	O1—C7—H7A	109.5
C8—C13—H13	119.9	O1—C7—H7B	109.5
C12—C13—H13	119.9	H7A—C7—H7B	109.5
O2—C14—H14A	109.5	O1—C7—H7C	109.5
O2—C14—H14B	109.5	H7A—C7—H7C	109.5
H14A—C14—H14B	109.5	H7B—C7—H7C	109.5
O2—C14—H14C	109.5	O5—N3—O3	120.8 (2)
H14A—C14—H14C	109.5	O5—N3—O4	122.17 (19)
H14B—C14—H14C	109.5	O3—N3—O4	117.03 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4i	0.89	2.25	2.823 (3)	122
N1—H1A···O7ii	0.89	2.52	2.979 (3)	113
N1—H1B···O6iii	0.89	2.26	2.843 (3)	123
N1—H1B···O5iv	0.89	2.12	2.903 (3)	146
N1—H1C···O7v	0.89	2.14	2.935 (3)	148
N2—H2A···O3i	0.89	2.08	2.967 (3)	177
N2—H2A···O4i	0.89	2.55	3.187 (3)	129
N2—H2B···O6vi	0.89	2.46	3.070 (3)	127
N2—H2B···O7vi	0.89	2.22	3.083 (3)	163
N2—H2C···O3	0.89	2.07	2.891 (2)	152
C9—H9···O8v	0.93	2.48	3.223 (3)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4i	0.89	2.25	2.823 (3)	122
N1—H1A⋯O7ii	0.89	2.52	2.979 (3)	113
N1—H1B⋯O6iii	0.89	2.26	2.843 (3)	123
N1—H1B⋯O5iv	0.89	2.12	2.903 (3)	146
N1—H1C⋯O7v	0.89	2.14	2.935 (3)	148
N2—H2A⋯O3i	0.89	2.08	2.967 (3)	177
N2—H2A⋯O4i	0.89	2.55	3.187 (3)	129
N2—H2B⋯O6vi	0.89	2.46	3.070 (3)	127
N2—H2B⋯O7vi	0.89	2.22	3.083 (3)	163
N2—H2C⋯O3	0.89	2.07	2.891 (2)	152
C9—H9⋯O8v	0.93	2.48	3.223 (3)	137

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