Benzyl­ammonium nitrate

The crystal structure of benzyl­ammonium nitrate, C₇H₁₀N⁺·NO₃⁻, exhibits ionic layers separated by hydro­carbon layers. The hydro­carbon layer contains the interdigitated benzyl groups, but no π–π interactions are observed. In the inorganic layer, the ammonium groups and nitrate ions interact via hydrogen-bonding.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.068
• wR factor = 0.172
• Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor ....       2.67
PLAT738_ALERT_1_C D-H..A  Calc   178.4(12), Rep      178(3) ......       2.50 su-Rat
              N1   -H1C  -O3      1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Bruno et al., 2002); software used to prepare material for publication: WinGX (Farrugia, 1999).

Benzylammonium nitrate

Crystal data

C7H10N^+·NO3^−	F(000) = 720
Mr = 170.17	Dx = 1.318 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 944 reflections
a = 9.817 (2) Å	θ = 2–32°
b = 11.043 (3) Å	µ = 0.10 mm^−1
c = 15.819 (4) Å	T = 120 K
V = 1714.9 (7) Å^3	Block, colourless
Z = 8	0.2 × 0.2 × 0.15 mm

Data collection

Oxford Excalibur2 diffractometer	1792 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.037
Graphite monochromator	θmax = 28.0°, θmin = 3.9°
ω–2θ scans	h = −12→11
13426 measured reflections	k = −14→14
2060 independent reflections	l = −20→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.172	H atoms treated by a mixture of independent and constrained refinement
S = 1.29	w = 1/[σ^2(Fo^2) + (0.085P)^2] where P = (Fo^2 + 2Fc^2)/3
2060 reflections	(Δ/σ)max = 0.026
121 parameters	Δρmax = 0.29 e Å^−3
15 restraints	Δρmin = −0.31 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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.

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

	x	y	z	Uiso*/Ueq
O2	0.52714 (14)	1.08618 (16)	0.29904 (10)	0.0265 (4)
C1	0.89985 (19)	0.8805 (2)	0.46285 (13)	0.0185 (5)
C6	0.9542 (2)	0.7694 (2)	0.50094 (14)	0.0238 (5)
H6	1.0275	0.7330	0.4737	0.029*
C7	0.9544 (2)	0.9432 (2)	0.38432 (13)	0.0234 (5)
H7A	0.9225	1.0264	0.3830	0.028*
H7B	1.0532	0.9444	0.3860	0.028*
C2	0.79586 (19)	0.9372 (2)	0.49952 (13)	0.0205 (5)
H2	0.7582	1.0082	0.4782	0.025*
C3	0.7481 (2)	0.8806 (2)	0.57320 (13)	0.0253 (5)
H3	0.6755	0.9172	0.6010	0.030*
C5	0.9062 (2)	0.7130 (2)	0.57448 (15)	0.0263 (5)
H5	0.9441	0.6423	0.5961	0.032*
N1	0.90714 (18)	0.8778 (2)	0.30571 (11)	0.0189 (4)
O1	0.72202 (14)	1.10996 (16)	0.31419 (10)	0.0274 (4)
O3	0.64631 (15)	0.91142 (15)	0.28442 (11)	0.0264 (4)
N2	0.63336 (17)	1.03605 (19)	0.29935 (11)	0.0209 (4)
C4	0.8026 (2)	0.7688 (2)	0.61023 (14)	0.0267 (6)
H4	0.7638	0.7373	0.6592	0.032*
H1A	0.922 (2)	0.792 (3)	0.3060 (16)	0.026 (7)*
H1B	0.947 (3)	0.924 (3)	0.259 (2)	0.055 (9)*
H1C	0.819 (3)	0.889 (2)	0.2975 (16)	0.031 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0087 (7)	0.0446 (11)	0.0263 (9)	0.0052 (6)	−0.0016 (6)	−0.0070 (7)
C1	0.0120 (9)	0.0293 (12)	0.0143 (10)	−0.0061 (8)	−0.0017 (7)	−0.0033 (9)
C6	0.0138 (9)	0.0356 (14)	0.0221 (11)	0.0007 (9)	−0.0006 (8)	−0.0060 (10)
C7	0.0143 (9)	0.0405 (14)	0.0153 (10)	−0.0081 (9)	−0.0001 (7)	−0.0045 (10)
C2	0.0142 (10)	0.0291 (13)	0.0183 (10)	−0.0016 (8)	−0.0021 (7)	−0.0005 (9)
C3	0.0118 (9)	0.0449 (15)	0.0192 (11)	−0.0047 (9)	0.0012 (8)	−0.0059 (10)
C5	0.0234 (11)	0.0298 (13)	0.0257 (12)	0.0000 (9)	−0.0073 (8)	0.0042 (10)
N1	0.0119 (9)	0.0303 (12)	0.0145 (9)	−0.0038 (7)	−0.0002 (6)	−0.0006 (8)
O1	0.0118 (7)	0.0357 (10)	0.0346 (10)	−0.0050 (6)	−0.0067 (6)	0.0005 (7)
O3	0.0158 (7)	0.0300 (10)	0.0333 (10)	−0.0003 (6)	−0.0033 (6)	−0.0022 (7)
N2	0.0137 (9)	0.0330 (11)	0.0161 (9)	0.0001 (7)	−0.0017 (6)	0.0011 (8)
C4	0.0214 (10)	0.0427 (15)	0.0160 (10)	−0.0129 (10)	−0.0013 (8)	0.0038 (10)

Geometric parameters (Å, º)

O2—N2	1.181 (2)	C3—C4	1.468 (3)
C1—C2	1.331 (3)	C3—H3	0.9300
C1—C6	1.467 (3)	C5—C4	1.317 (3)
C1—C7	1.520 (3)	C5—H5	0.9300
C6—C5	1.402 (3)	N1—H1A	0.96 (3)
C6—H6	0.9300	N1—H1B	0.99 (4)
C7—N1	1.511 (3)	N1—H1C	0.89 (3)
C7—H7A	0.9700	O1—N2	1.216 (2)
C7—H7B	0.9700	O3—N2	1.402 (3)
C2—C3	1.403 (3)	C4—H4	0.9300
C2—H2	0.9300
C2—C1—C6	119.6 (2)	C4—C3—H3	117.1
C2—C1—C7	114.3 (2)	C4—C5—C6	114.1 (2)
C6—C1—C7	126.06 (19)	C4—C5—H5	123.0
C5—C6—C1	126.2 (2)	C6—C5—H5	123.0
C5—C6—H6	116.9	C7—N1—H1A	115.0 (16)
C1—C6—H6	116.9	C7—N1—H1B	105 (2)
N1—C7—C1	110.24 (17)	H1A—N1—H1B	117 (2)
N1—C7—H7A	109.6	C7—N1—H1C	111.0 (17)
C1—C7—H7A	109.6	H1A—N1—H1C	106 (2)
N1—C7—H7B	109.6	H1B—N1—H1C	102 (3)
C1—C7—H7B	109.6	O2—N2—O1	108.6 (2)
H7A—C7—H7B	108.1	O2—N2—O3	122.66 (18)
C1—C2—C3	114.1 (2)	O1—N2—O3	128.78 (17)
C1—C2—H2	122.9	C5—C4—C3	120.3 (2)
C3—C2—H2	122.9	C5—C4—H4	119.9
C2—C3—C4	125.7 (2)	C3—C4—H4	119.9
C2—C3—H3	117.1

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O2^i	0.99 (4)	2.15 (3)	3.071 (3)	154 (3)
N1—H1C···O3	0.89 (3)	1.72 (3)	2.609 (2)	178 (3)
N1—H1A···O2^ii	0.96 (3)	2.33 (3)	3.286 (3)	175 (2)
N1—H1A···O1^ii	0.96 (3)	2.46 (3)	3.221 (3)	136 (2)
N1—H1B···O3^i	0.99 (4)	2.08 (3)	2.772 (2)	126 (3)

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