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

In the title compound, C(9)H(12)NO(2) (+)·ClO(4) (-), an intra-molecular N-H⋯O inter-action results in the formation of a six-membered ring having a twisted chair conformation. In the crystal structure, inter-molecular O-H⋯O, N-H⋯O and C-H⋯O inter-actions link the mol-ecules into a network. A weak C-H⋯π inter-action is also found.

Related literature

There has been an increased inter­est in the enanti­omeric preparation of β-amino acids as precursors for the synthesis of novel biologically active compounds, see: Arki et al. (2004 ▶); Cohen et al. (2002 ▶); Zeller et al. (1965 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C9H12NO2 +·n class="Chemical">ClO4 −

M = 265.65

Orthorhombic,

a = 6.6583 (13) Å

b = 13.826 (3) Å

c = 24.300 (5) Å

V = 2237.0 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.36 mm−1

T = 294 K

0.45 × 0.35 × 0.12 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.863, T max = 0.957

21012 measured reflections

2560 independent reflections

1966 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.110

S = 1.10

2560 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.37 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809016171/hk2675sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016171/hk2675Isup2.hkl

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

C9H12NO2+·ClO4−	F(000) = 1104
Mr = 265.65	Dx = 1.578 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1979 reflections
a = 6.6583 (13) Å	θ = 3.1–27.5°
b = 13.826 (3) Å	µ = 0.36 mm−1
c = 24.300 (5) Å	T = 294 K
V = 2237.0 (8) Å3	Prism, colorless
Z = 8	0.45 × 0.35 × 0.12 mm

Rigaku SCXmini diffractometer	2560 independent reflections
Radiation source: fine-focus sealed tube	1966 reflections with I > 2σ(I)
graphite	Rint = 0.058
CCD_Profile_fitting scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (Blessing, 1995)	h = −8→8
Tmin = 0.863, Tmax = 0.957	k = −17→17
21012 measured reflections	l = −31→31

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0351P)2 + 1.6729P] where P = (Fo2 + 2Fc2)/3
2560 reflections	(Δ/σ)max < 0.001
156 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.37 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
Cl1	0.99041 (8)	0.97917 (4)	0.32015 (2)	0.03337 (17)
O1	0.9660 (3)	0.30715 (14)	0.32107 (7)	0.0428 (5)
H1	1.0262	0.3182	0.2923	0.064*
O2	0.7570 (2)	0.22973 (13)	0.26501 (6)	0.0365 (4)
O3	1.0688 (3)	1.07288 (12)	0.30762 (7)	0.0439 (5)
O4	0.9012 (3)	0.94103 (16)	0.27168 (8)	0.0630 (6)
O5	1.1483 (3)	0.91952 (15)	0.33824 (10)	0.0649 (6)
O6	0.8413 (3)	0.98786 (15)	0.36203 (8)	0.0584 (6)
N1	0.4988 (3)	0.09957 (16)	0.31532 (7)	0.0349 (5)
H1A	0.5772	0.0550	0.3307	0.052*
H1B	0.5491	0.1165	0.2828	0.052*
H1C	0.3759	0.0756	0.3107	0.052*
C1	0.8076 (3)	0.25365 (17)	0.31064 (9)	0.0289 (5)
C2	0.6999 (3)	0.22487 (17)	0.36217 (9)	0.0306 (5)
H2A	0.6911	0.2806	0.3863	0.037*
H2B	0.7778	0.1756	0.3810	0.037*
C3	0.4889 (3)	0.18613 (17)	0.35177 (9)	0.0289 (5)
H3	0.4139	0.2364	0.3321	0.035*
C4	0.3749 (3)	0.16333 (17)	0.40392 (9)	0.0310 (5)
C5	0.3897 (4)	0.0760 (2)	0.43014 (10)	0.0464 (7)
H5	0.4766	0.0289	0.4167	0.056*
C6	0.2752 (5)	0.0576 (2)	0.47670 (12)	0.0565 (8)
H6	0.2840	−0.0023	0.4940	0.068*
C7	0.1499 (4)	0.1267 (2)	0.49722 (11)	0.0537 (8)
H7	0.0739	0.1143	0.5286	0.064*
C8	0.1367 (4)	0.2138 (2)	0.47155 (11)	0.0493 (7)
H8	0.0524	0.2613	0.4857	0.059*
C9	0.2472 (4)	0.2322 (2)	0.42480 (9)	0.0390 (6)
H9	0.2352	0.2916	0.4072	0.047*

	U11	U22	U33	U12	U13	U23
Cl1	0.0277 (3)	0.0306 (3)	0.0418 (3)	−0.0002 (2)	0.0000 (2)	0.0054 (3)
O1	0.0336 (10)	0.0582 (12)	0.0365 (9)	−0.0188 (8)	0.0033 (8)	−0.0024 (9)
O2	0.0335 (9)	0.0489 (10)	0.0270 (8)	−0.0081 (8)	0.0018 (7)	−0.0040 (7)
O3	0.0422 (10)	0.0332 (10)	0.0564 (11)	−0.0080 (8)	−0.0014 (9)	0.0095 (8)
O4	0.0594 (13)	0.0684 (14)	0.0612 (13)	−0.0217 (11)	−0.0103 (11)	−0.0133 (11)
O5	0.0553 (13)	0.0554 (13)	0.0841 (15)	0.0219 (11)	−0.0044 (12)	0.0233 (11)
O6	0.0517 (12)	0.0644 (13)	0.0591 (12)	0.0037 (10)	0.0210 (10)	0.0119 (11)
N1	0.0307 (11)	0.0439 (12)	0.0300 (10)	−0.0085 (9)	0.0019 (9)	−0.0045 (9)
C1	0.0242 (11)	0.0291 (12)	0.0333 (12)	0.0002 (9)	0.0011 (9)	−0.0020 (10)
C2	0.0296 (12)	0.0359 (13)	0.0262 (11)	−0.0056 (10)	−0.0013 (9)	−0.0024 (10)
C3	0.0253 (11)	0.0355 (13)	0.0259 (11)	0.0009 (10)	0.0013 (9)	−0.0003 (9)
C4	0.0238 (11)	0.0435 (14)	0.0256 (11)	−0.0039 (10)	−0.0005 (9)	0.0008 (10)
C5	0.0485 (16)	0.0501 (16)	0.0406 (14)	0.0037 (13)	0.0071 (13)	0.0065 (13)
C6	0.066 (2)	0.0596 (19)	0.0435 (16)	−0.0121 (16)	0.0047 (15)	0.0180 (14)
C7	0.0425 (16)	0.085 (2)	0.0339 (14)	−0.0167 (16)	0.0088 (12)	0.0037 (15)
C8	0.0388 (15)	0.073 (2)	0.0363 (14)	0.0045 (14)	0.0094 (12)	−0.0057 (14)
C9	0.0323 (12)	0.0520 (16)	0.0326 (12)	0.0016 (11)	0.0003 (11)	0.0012 (12)

Cl1—O5	1.4067 (19)	C3—N1	1.490 (3)
Cl1—O4	1.421 (2)	C3—C4	1.510 (3)
Cl1—O6	1.4269 (19)	C3—H3	0.9800
Cl1—O3	1.4297 (18)	C4—C5	1.369 (3)
O1—H1	0.8200	C4—C9	1.373 (3)
N1—H1A	0.8900	C5—C6	1.388 (4)
N1—H1B	0.8900	C5—H5	0.9300
N1—H1C	0.8900	C6—C7	1.363 (4)
C1—O2	1.205 (3)	C6—H6	0.9300
C1—O1	1.313 (3)	C7—C8	1.359 (4)
C1—C2	1.497 (3)	C7—H7	0.9300
C2—C3	1.524 (3)	C8—C9	1.377 (3)
C2—H2A	0.9700	C8—H8	0.9300
C2—H2B	0.9700	C9—H9	0.9300
O5—Cl1—O4	110.73 (15)	N1—C3—C2	109.89 (18)
O5—Cl1—O6	110.28 (13)	C4—C3—C2	113.42 (18)
O4—Cl1—O6	109.36 (13)	N1—C3—H3	107.5
O5—Cl1—O3	108.97 (12)	C4—C3—H3	107.5
O4—Cl1—O3	108.21 (12)	C2—C3—H3	107.5
O6—Cl1—O3	109.25 (12)	C5—C4—C9	119.0 (2)
C1—O1—H1	109.5	C5—C4—C3	122.6 (2)
C3—N1—H1A	109.5	C9—C4—C3	118.5 (2)
C3—N1—H1B	109.5	C4—C5—C6	120.1 (3)
C3—N1—H1C	109.5	C4—C5—H5	120.0
H1A—N1—H1B	109.5	C6—C5—H5	120.0
H1A—N1—H1C	109.5	C7—C6—C5	120.4 (3)
H1B—N1—H1C	109.5	C7—C6—H6	119.8
O2—C1—O1	123.8 (2)	C5—C6—H6	119.8
O2—C1—C2	124.2 (2)	C8—C7—C6	119.5 (3)
O1—C1—C2	111.91 (19)	C8—C7—H7	120.2
C1—C2—C3	113.35 (18)	C6—C7—H7	120.2
C1—C2—H2A	108.9	C7—C8—C9	120.5 (3)
C3—C2—H2A	108.9	C7—C8—H8	119.7
C1—C2—H2B	108.9	C9—C8—H8	119.7
C3—C2—H2B	108.9	C4—C9—C8	120.5 (3)
H2A—C2—H2B	107.7	C4—C9—H9	119.7
N1—C3—C4	110.68 (19)	C8—C9—H9	119.7

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O2	0.89	2.13	2.773 (3)	128
C9—H9···O5i	0.93	2.56	3.409 (3)	152
C3—H3···O5i	0.98	2.57	3.370 (3)	139
C3—H3···O2ii	0.98	2.58	3.286 (3)	129
N1—H1C···O3iii	0.89	2.05	2.892 (3)	158
N1—H1B···O3iv	0.89	2.28	3.046 (3)	144
N1—H1A···O6v	0.89	2.13	2.979 (3)	159
O1—H1···O2vi	0.82	2.41	3.046 (2)	135
O1—H1···O4vii	0.82	2.35	3.048 (3)	143
C8—H8···Cg1viii	0.93	2.79	3.688 (3)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O2	0.89	2.13	2.773 (3)	128
C9—H9⋯O5i	0.93	2.56	3.409 (3)	152
C3—H3⋯O5i	0.98	2.57	3.370 (3)	139
C3—H3⋯O2ii	0.98	2.58	3.286 (3)	129
N1—H1C⋯O3iii	0.89	2.05	2.892 (3)	158
N1—H1B⋯O3iv	0.89	2.28	3.046 (3)	144
N1—H1A⋯O6v	0.89	2.13	2.979 (3)	159
O1—H1⋯O2vi	0.82	2.41	3.046 (2)	135
O1—H1⋯O4vii	0.82	2.35	3.048 (3)	143
C8—H8⋯Cg1viii	0.93	2.79	3.688 (3)	162

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) . Cg1 is the centroid of the C4–C9 ring.