2-Carb-oxy-1-phenyl-ethanaminium nitrate.

In the title salt, C(9)H(12)NO(2) (+)·NO(3) (-), the cation and anion are linked by a bifurcated N-H⋯(O,O) hydrogen bond. The crystal packing is stabilized by inter-molecular N-H⋯O, O-H⋯O and C-H⋯O hydrogen bonds, which connect neighbouring cations and anions, resulting in a two-dimensional network.

Related literature

For details of the preparation of β-amino acids, see: Cohen et al. (2002 ▶); Qu et al. (2004 ▶).

Experimental

Crystal data

C9H12NO2 +·NO3 −

M = 228.21

Monoclinic,

a = 6.2017 (12) Å

b = 10.313 (2) Å

c = 18.077 (4) Å

β = 105.36 (3)°

V = 1114.9 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.50 × 0.30 × 0.15 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.960, T max = 0.982

11050 measured reflections

2549 independent reflections

1652 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.080

wR(F 2) = 0.231

S = 1.11

2549 reflections

149 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.59 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrystalClear (Rigaku 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: PRPKAPPA (Ferguson, 1999 ▶).

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536809042792/sj2656sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042792/sj2656Isup2.hkl

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

C9H12NO2+·NO3−	F(000) = 480
Mr = 228.21	Dx = 1.360 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1797 reflections
a = 6.2017 (12) Å	θ = 3.1–27.5°
b = 10.313 (2) Å	µ = 0.11 mm−1
c = 18.077 (4) Å	T = 293 K
β = 105.36 (3)°	Prism, colorless
V = 1114.9 (4) Å3	0.50 × 0.30 × 0.15 mm
Z = 4

Rigaku SCXmini diffractometer	2549 independent reflections
Radiation source: fine-focus sealed tube	1652 reflections with I > 2σ(I)
graphite	Rint = 0.061
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.1°
CCD_Profile_fitting scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −13→13
Tmin = 0.960, Tmax = 0.982	l = −23→23
11050 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)] = 0.080	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.231	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0829P)2 + 1.0943P] where P = (Fo2 + 2Fc2)/3
2549 reflections	(Δ/σ)max < 0.001
149 parameters	Δρmax = 0.59 e Å−3
1 restraint	Δρmin = −0.23 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	1.1549 (5)	0.1241 (2)	0.30410 (14)	0.0613 (8)
O2	0.8967 (5)	0.2333 (3)	0.34151 (16)	0.0631 (8)
H2	0.9252	0.1813	0.3771	0.095*
N1	0.7398 (5)	0.3900 (2)	0.11238 (14)	0.0382 (6)
H1A	0.6020	0.3868	0.0823	0.066 (12)*
H1B	0.7688	0.4697	0.1305	0.050 (10)*
H1C	0.8352	0.3690	0.0856	0.050 (11)*
C3	1.0254 (6)	0.2102 (3)	0.29593 (19)	0.0466 (8)
C4	0.6953 (6)	0.1620 (3)	0.14746 (19)	0.0442 (8)
C1	0.7597 (6)	0.2980 (3)	0.17750 (18)	0.0434 (8)
H1	0.6540	0.3255	0.2063	0.052*
C2	0.9930 (6)	0.3062 (3)	0.23070 (19)	0.0505 (9)
H2A	1.1015	0.2890	0.2019	0.061*
H2B	1.0190	0.3933	0.2514	0.061*
C7	0.5759 (11)	−0.0891 (4)	0.0971 (3)	0.0857 (17)
H7	0.5361	−0.1733	0.0805	0.103*
C8	0.4647 (9)	−0.0261 (5)	0.1410 (4)	0.0903 (18)
H8	0.3468	−0.0675	0.1541	0.108*
C5	0.8088 (8)	0.0973 (4)	0.1026 (2)	0.0620 (11)
H5	0.9274	0.1374	0.0892	0.074*
C9	0.5224 (7)	0.1002 (4)	0.1675 (3)	0.0649 (11)
H9	0.4448	0.1417	0.1982	0.078*
C6	0.7458 (10)	−0.0285 (5)	0.0774 (3)	0.0817 (16)
H6	0.8219	−0.0711	0.0466	0.098*
O3	0.3218 (4)	0.3769 (3)	−0.01018 (15)	0.0562 (7)
O4	0.2293 (5)	0.3826 (3)	0.09586 (15)	0.0706 (9)
O5	−0.0245 (4)	0.3499 (3)	−0.00958 (16)	0.0597 (7)
N2	0.1772 (5)	0.3697 (3)	0.02545 (17)	0.0457 (7)

	U11	U22	U33	U12	U13	U23
O1	0.094 (2)	0.0400 (14)	0.0476 (15)	0.0168 (14)	0.0138 (14)	0.0082 (11)
O2	0.0649 (18)	0.0546 (16)	0.0658 (18)	0.0237 (13)	0.0100 (14)	0.0187 (13)
N1	0.0436 (15)	0.0318 (14)	0.0352 (14)	−0.0020 (11)	0.0035 (12)	0.0044 (11)
C3	0.060 (2)	0.0397 (18)	0.0345 (17)	0.0015 (16)	0.0034 (15)	−0.0028 (14)
C4	0.053 (2)	0.0337 (16)	0.0381 (17)	−0.0049 (14)	−0.0023 (15)	0.0075 (14)
C1	0.0523 (19)	0.0366 (17)	0.0377 (17)	−0.0064 (14)	0.0055 (14)	0.0062 (13)
C2	0.059 (2)	0.0430 (19)	0.043 (2)	−0.0033 (16)	0.0017 (17)	0.0061 (15)
C7	0.110 (4)	0.037 (2)	0.079 (3)	−0.010 (3)	−0.028 (3)	0.002 (2)
C8	0.081 (3)	0.058 (3)	0.110 (4)	−0.032 (3)	−0.012 (3)	0.022 (3)
C5	0.078 (3)	0.046 (2)	0.056 (2)	0.0012 (19)	0.009 (2)	0.0072 (18)
C9	0.058 (2)	0.051 (2)	0.082 (3)	−0.0113 (18)	0.012 (2)	0.011 (2)
C6	0.125 (5)	0.052 (3)	0.054 (3)	0.017 (3)	−0.001 (3)	−0.002 (2)
O3	0.0519 (15)	0.0685 (17)	0.0521 (15)	−0.0016 (12)	0.0203 (12)	0.0067 (13)
O4	0.0683 (18)	0.105 (2)	0.0385 (15)	0.0053 (16)	0.0137 (13)	0.0178 (15)
O5	0.0421 (14)	0.0672 (17)	0.0668 (18)	−0.0069 (12)	0.0093 (12)	−0.0081 (14)
N2	0.0524 (17)	0.0380 (15)	0.0472 (17)	0.0036 (12)	0.0142 (14)	0.0113 (13)

O1—C3	1.180 (4)	C2—H2B	0.9700
O2—C3	1.312 (4)	C7—C8	1.349 (8)
O2—H2	0.8200	C7—C6	1.352 (8)
N1—C1	1.492 (4)	C7—H7	0.9300
N1—H1A	0.8837	C8—C9	1.401 (7)
N1—H1B	0.8848	C8—H8	0.9300
N1—H1C	0.8849	C5—C6	1.396 (6)
C3—C2	1.512 (5)	C5—H5	0.9300
C4—C9	1.375 (5)	C9—H9	0.9300
C4—C5	1.378 (5)	C6—H6	0.9300
C4—C1	1.519 (5)	O3—N2	1.237 (4)
C1—C2	1.513 (5)	O4—N2	1.235 (4)
C1—H1	0.9800	O5—N2	1.260 (4)
C2—H2A	0.9700
C3—O2—H2	109.5	C3—C2—H2B	109.3
C1—N1—H1A	109.0	C1—C2—H2B	109.3
C1—N1—H1B	109.4	H2A—C2—H2B	108.0
H1A—N1—H1B	109.4	C8—C7—C6	119.2 (4)
C1—N1—H1C	110.4	C8—C7—H7	120.4
H1A—N1—H1C	109.4	C6—C7—H7	120.4
H1B—N1—H1C	109.3	C7—C8—C9	121.7 (5)
O1—C3—O2	124.4 (3)	C7—C8—H8	119.2
O1—C3—C2	122.4 (3)	C9—C8—H8	119.2
O2—C3—C2	113.2 (3)	C4—C5—C6	120.0 (5)
C9—C4—C5	119.1 (4)	C4—C5—H5	120.0
C9—C4—C1	118.9 (4)	C6—C5—H5	120.0
C5—C4—C1	122.0 (3)	C4—C9—C8	119.2 (5)
N1—C1—C2	109.3 (3)	C4—C9—H9	120.4
N1—C1—C4	110.3 (3)	C8—C9—H9	120.4
C2—C1—C4	113.3 (3)	C7—C6—C5	121.0 (5)
N1—C1—H1	107.9	C7—C6—H6	119.5
C2—C1—H1	107.9	C5—C6—H6	119.5
C4—C1—H1	107.9	O4—N2—O3	120.2 (3)
C3—C2—C1	111.5 (3)	O4—N2—O5	119.3 (3)
C3—C2—H2A	109.3	O3—N2—O5	120.5 (3)
C1—C2—H2A	109.3

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2i	0.93	2.56	3.414 (5)	152
C2—H2A···O4ii	0.97	2.46	3.256 (5)	140
O2—H2···O5iii	0.82	2.01	2.743 (4)	148
N1—H1C···O5ii	0.88	2.13	2.979 (4)	160
N1—H1C···O4ii	0.88	2.41	3.129 (4)	139
N1—H1B···O1iv	0.88	1.97	2.830 (4)	166
N1—H1A···O4	0.88	2.39	3.101 (4)	138
N1—H1A···O3	0.88	2.07	2.933 (4)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O2i	0.93	2.56	3.414 (5)	152
C2—H2A⋯O4ii	0.97	2.46	3.256 (5)	140
O2—H2⋯O5iii	0.82	2.01	2.743 (4)	148
N1—H1C⋯O5ii	0.88	2.13	2.979 (4)	160
N1—H1C⋯O4ii	0.88	2.41	3.129 (4)	139
N1—H1B⋯O1iv	0.88	1.97	2.830 (4)	166
N1—H1A⋯O4	0.88	2.39	3.101 (4)	138
N1—H1A⋯O3	0.88	2.07	2.933 (4)	165

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