4-Meth­oxy­benzyl­ammonium nitrate

In the title salt, C₈H₁₂NO⁺·NO₃⁻, the 4-meth­oxy­benzyl­ammonium cation lies in the mirror plane m of space group Pnma and is thus planar by symmetry. The nitrate anion is also planar by symmetry, with an N[pdbond]O group in the mirror plane and one O atom in a general position. The dihedral angle between the benzene ring and the planar nitrate anion is constrained to be exactly 90°, because of the relative special positions for both ions. In the crystal, the cations are connected to the anions by C—H...O, C—H...N, N—H...N and N—H...O hydrogen bonds. Further, the crystal structure also features two C—H...π inter­actions involving the benzene ring of the cation, forming a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.040
• wR factor = 0.131
• Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         N2 Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1B    ..  N2      ..       2.67 Ang.
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -5.497 Report

Alert level G
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         57 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          6 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2015); software used to prepare material for publication: publCIF (Westrip, 2010).

4-Methoxybenzylammonium nitrate

Crystal data

C8H12NO^+·NO3^−	Dx = 1.413 Mg m^−3
Mr = 200.20	Melting point: 375 K
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
a = 15.8203 (17) Å	Cell parameters from 4546 reflections
b = 6.8156 (7) Å	θ = 2.6–29.6°
c = 8.7275 (8) Å	µ = 0.11 mm^−1
V = 941.04 (16) Å^3	T = 296 K
Z = 4	Block, colourless
F(000) = 424	0.25 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer	1126 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.038
ω and φ scan	θmax = 31.7°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −23→23
Tmin = 0.696, Tmax = 0.746	k = −9→9
18099 measured reflections	l = −12→12
1663 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.131	w = 1/[σ^2(Fo^2) + (0.0547P)^2 + 0.2894P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
1663 reflections	Δρmax = 0.30 e Å^−3
101 parameters	Δρmin = −0.19 e Å^−3
0 restraints	Extinction correction: SHELXL2017 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 constraints	Extinction coefficient: 0.021 (3)
Primary atom site location: structure-invariant direct methods

Special details

Refinement. The N-bound H atoms, CH₂ H atoms and CH₃ H atoms were located in a difference Fourier map and refined freely; N1—H1A = 0.92 (3) and N1—H1B = 0.96 (2) Å, C8—H8 = 0.971 (18), C1—H1C = 0.98 (3) and C1—H1D = 0.978 (19) Å. The remaining H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93 Å (aromatic); U_iso(H) = 1.2U_eq(C).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.45170 (15)	0.250000	0.6753 (2)	0.0419 (5)
C2	0.47135 (11)	0.250000	0.4038 (2)	0.0305 (4)
C3	0.55852 (11)	0.250000	0.4177 (2)	0.0341 (4)
H3	0.583441	0.250000	0.514185	0.041*
C4	0.60883 (11)	0.250000	0.2864 (2)	0.0334 (4)
H4	0.667343	0.250000	0.296668	0.040*
C5	0.57361 (11)	0.250000	0.14141 (19)	0.0291 (4)
C6	0.48549 (11)	0.250000	0.1299 (2)	0.0353 (4)
H6	0.460461	0.250000	0.033433	0.042*
C7	0.43498 (11)	0.250000	0.2584 (2)	0.0373 (4)
H7	0.376470	0.250000	0.248118	0.045*
C8	0.62382 (12)	0.250000	−0.0055 (2)	0.0388 (4)
N1	0.71654 (11)	0.250000	0.0170 (2)	0.0377 (4)
N2	0.74586 (10)	0.750000	0.12747 (17)	0.0354 (4)
O1	0.41614 (8)	0.250000	0.52492 (15)	0.0414 (4)
O2	0.76246 (8)	0.59369 (17)	0.19519 (14)	0.0569 (4)
O3	0.71238 (11)	0.750000	0.00086 (18)	0.0616 (5)
H1A	0.7431 (17)	0.250000	−0.076 (4)	0.059 (7)*
H1B	0.7340 (13)	0.134 (3)	0.071 (3)	0.077 (6)*
H1C	0.404 (2)	0.250000	0.747 (4)	0.077 (9)*
H1D	0.4873 (11)	0.135 (3)	0.692 (2)	0.058 (5)*
H8	0.6126 (11)	0.135 (3)	−0.067 (2)	0.061 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0487 (12)	0.0453 (12)	0.0317 (9)	0.000	0.0074 (8)	0.000
C2	0.0310 (8)	0.0295 (8)	0.0312 (8)	0.000	0.0025 (6)	0.000
C3	0.0326 (9)	0.0433 (10)	0.0264 (8)	0.000	−0.0036 (7)	0.000
C4	0.0255 (8)	0.0442 (10)	0.0306 (8)	0.000	−0.0017 (6)	0.000
C5	0.0291 (8)	0.0301 (8)	0.0280 (8)	0.000	−0.0007 (6)	0.000
C6	0.0338 (9)	0.0435 (10)	0.0287 (8)	0.000	−0.0067 (7)	0.000
C7	0.0257 (8)	0.0485 (11)	0.0377 (9)	0.000	−0.0045 (7)	0.000
C8	0.0352 (9)	0.0529 (13)	0.0284 (8)	0.000	−0.0003 (7)	0.000
N1	0.0357 (8)	0.0455 (10)	0.0319 (8)	0.000	0.0053 (6)	0.000
N2	0.0278 (7)	0.0464 (9)	0.0319 (7)	0.000	0.0016 (6)	0.000
O1	0.0337 (7)	0.0559 (9)	0.0347 (7)	0.000	0.0057 (5)	0.000
O2	0.0783 (8)	0.0383 (6)	0.0541 (7)	−0.0045 (5)	−0.0173 (6)	0.0043 (5)
O3	0.0567 (10)	0.0924 (14)	0.0357 (8)	0.000	−0.0140 (7)	0.000

Geometric parameters (Å, º)

C1—O1	1.428 (2)	C5—C8	1.508 (2)
C1—H1C	0.98 (3)	C6—C7	1.377 (3)
C1—H1D	0.978 (19)	C6—H6	0.9300
C1—H1D^i	0.978 (19)	C7—H7	0.9300
C2—O1	1.371 (2)	C8—N1	1.480 (3)
C2—C3	1.384 (2)	C8—H8	0.971 (18)
C2—C7	1.393 (2)	C8—H8^i	0.971 (18)
C3—C4	1.395 (2)	N1—H1A	0.92 (3)
C3—H3	0.9300	N1—H1B	0.96 (2)
C4—C5	1.383 (2)	N2—O3	1.225 (2)
C4—H4	0.9300	N2—O2^ii	1.2463 (14)
C5—C6	1.398 (2)	N2—O2	1.2463 (14)
O1—C1—H1C	106.1 (18)	C7—C6—H6	119.3
O1—C1—H1D	111.3 (11)	C5—C6—H6	119.3
H1C—C1—H1D	110.5 (14)	C6—C7—C2	120.15 (16)
O1—C1—H1D^i	111.3 (11)	C6—C7—H7	119.9
H1C—C1—H1D^i	110.5 (14)	C2—C7—H7	119.9
H1D—C1—H1D^i	107 (2)	N1—C8—C5	114.15 (15)
O1—C2—C3	124.53 (15)	N1—C8—H8	104.8 (10)
O1—C2—C7	116.05 (15)	C5—C8—H8	112.1 (11)
C3—C2—C7	119.43 (16)	N1—C8—H8^i	104.8 (10)
C2—C3—C4	119.76 (16)	C5—C8—H8^i	112.1 (11)
C2—C3—H3	120.1	H8—C8—H8^i	108 (2)
C4—C3—H3	120.1	C8—N1—H1A	109.6 (17)
C5—C4—C3	121.44 (15)	C8—N1—H1B	110.5 (12)
C5—C4—H4	119.3	H1A—N1—H1B	107.8 (15)
C3—C4—H4	119.3	O3—N2—O2^ii	121.25 (8)
C4—C5—C6	117.90 (15)	O3—N2—O2	121.25 (8)
C4—C5—C8	124.46 (15)	O2^ii—N2—O2	117.48 (16)
C6—C5—C8	117.64 (15)	C2—O1—C1	117.24 (14)
C7—C6—C5	121.32 (16)
O1—C2—C3—C4	180.000 (1)	C5—C6—C7—C2	0.000 (1)
C7—C2—C3—C4	0.000 (1)	O1—C2—C7—C6	180.000 (1)
C2—C3—C4—C5	0.000 (1)	C3—C2—C7—C6	0.000 (1)
C3—C4—C5—C6	0.000 (1)	C4—C5—C8—N1	0.0
C3—C4—C5—C8	180.000 (1)	C6—C5—C8—N1	180.0
C4—C5—C6—C7	0.000 (1)	C3—C2—O1—C1	0.000 (1)
C8—C5—C6—C7	180.000 (1)	C7—C2—O1—C1	180.000 (1)

Symmetry codes: (i) x, −y+1/2, z; (ii) x, −y+3/2, z.

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O3^iii	0.93	2.59	3.249 (2)	128
C1—H1C···N2^iv	0.98 (3)	2.61 (3)	3.568 (3)	166 (3)
N1—H1A···N2^v	0.92 (3)	2.59 (3)	3.452 (2)	157 (2)
N1—H1A···O2^v	0.92 (3)	2.26 (3)	3.022 (2)	140 (2)
N1—H1A···O2^vi	0.92 (3)	2.26 (3)	3.022 (2)	140 (2)
N1—H1B···N2^vii	0.96 (2)	2.67 (2)	3.5717 (8)	156.4 (18)
N1—H1B···O2^i	0.96 (2)	1.94 (2)	2.9039 (16)	175.0 (19)
C1—H1D···Cg1^viii	0.978 (19)	2.65 (2)	3.4625 (5)	141.4 (14)
C1—H1D···Cg1^ix	0.978 (19)	2.65 (2)	3.4625 (5)	141.4 (14)

Symmetry codes: (i) x, −y+1/2, z; (iii) −x+1, −y+1, −z; (iv) −x+1, −y+1, −z+1; (v) −x+3/2, −y+1, z−1/2; (vi) −x+3/2, y−1/2, z−1/2; (vii) x, y−1, z; (viii) x+3/2, −y−1/2, −z+3/2; (ix) −x+1, −y, −z+1.