Redetermination of 1-carboxy-cyclo-hexan-1-aminium chloride.

The crystal structure of the title compound, C(7)H(14)NO(2) (+)·Cl(-), was reported previously [Chacko, Srinivasan & Zand (1975 ▶). J. Cryst. Mol. Struct.5, 353-357] from Weissenberg photographic data with R = 0.113. It has now been redetermined, providing a significant increase in the precision of the derived geometric parameters, viz. mean σ(C-C) = 0.003 Å in the present work compared with 0.021 Å for the previous work. The complete cation is generated by crystallographic mirrror symmetry, with three C atoms, two O atoms and the N atom lying on the reflecting plane; the chloride anion also has m site symmetry. The crystal structure is established by a two-dimensional network of O-H⋯Cl and N-H⋯Cl hydrogen bonds, generating C(1) (2)(4) and C(1) (2)(7) chains, and R(2) (4)(8) and R(2) (4)(14) rings.

Related literature

For the earlier structure determination of the title salt, see: Chacko et al. (1971 ▶, 1975 ▶). For related literature, see Rodríguez-Ropero et al. (2008 ▶). For the crystal structure of the pure amino acid, see: Valle et al. (1988 ▶). For ring conformation analysis, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs in graph-set notation, see: Etter (1990 ▶).

Experimental

Crystal data

C7H14NO2 +·Cl−

M = 179.64

Monoclinic,

a = 7.382 (3) Å

b = 6.357 (2) Å

c = 9.374 (3) Å

β = 96.239 (10)°

V = 437.3 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.39 mm−1

T = 298 (2) K

0.31 × 0.27 × 0.18 mm

Data collection

Rigaku AFC-7S Mercury diffractometer

Absorption correction: multi-scan (Jacobson, 1998 ▶) T min = 0.880, T max = 0.930

4638 measured reflections

845 independent reflections

789 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.088

S = 1.01

845 reflections

85 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrystalClear (Rigaku, 2002 ▶); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶) and publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808044243/bh2212sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808044243/bh2212Isup2.hkl

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

C7H14NO2+·Cl−	F(000) = 192
Mr = 179.64	Dx = 1.364 Mg m−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2yb	Cell parameters from 1650 reflections
a = 7.382 (3) Å	θ = 2.2–27.2°
b = 6.357 (2) Å	µ = 0.39 mm−1
c = 9.374 (3) Å	T = 298 K
β = 96.239 (10)°	Block, colourless
V = 437.3 (3) Å3	0.31 × 0.27 × 0.18 mm
Z = 2

Rigaku AFC-7S Mercury diffractometer	845 independent reflections
Radiation source: Normal-focus sealed tube	789 reflections with I > 2σ(I)
graphite	Rint = 0.023
Detector resolution: 14.6306 pixels mm-1	θmax = 25.0°, θmin = 2.2°
ω scans	h = −8→8
Absorption correction: multi-scan (Jacobson, 1998)	k = −6→7
Tmin = 0.880, Tmax = 0.930	l = −11→11
4638 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.088	w = 1/[σ2(Fo2) + (0.047P)2 + 0.1831P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
845 reflections	Δρmax = 0.18 e Å−3
85 parameters	Δρmin = −0.15 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraints	Extinction coefficient: 0.042 (10)
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
Cl	0.41343 (8)	0.2500	0.64377 (6)	0.0414 (3)
O2	0.5446 (2)	0.2500	0.04758 (18)	0.0511 (5)
O1	0.2629 (3)	0.2500	−0.06850 (18)	0.0528 (5)
H1	0.324 (5)	0.2500	−0.146 (4)	0.079*
N1	0.4370 (3)	0.2500	0.3054 (2)	0.0343 (5)
H1A	0.506 (3)	0.138 (3)	0.300 (2)	0.051*
H1B	0.398 (4)	0.2500	0.393 (3)	0.051*
C1	0.2863 (3)	0.2500	0.1837 (2)	0.0292 (5)
C2	0.1715 (2)	0.4484 (3)	0.19289 (19)	0.0408 (5)
H2A	0.251 (3)	0.566 (3)	0.1923 (19)	0.049*
H2B	0.090 (3)	0.452 (3)	0.107 (2)	0.049*
C3	0.0597 (3)	0.4450 (4)	0.3193 (2)	0.0539 (6)
H3A	0.140 (3)	0.449 (4)	0.409 (2)	0.065*
H3B	−0.018 (3)	0.571 (4)	0.315 (2)	0.065*
C4	−0.0557 (4)	0.2500	0.3201 (3)	0.0626 (9)
H4A	−0.145 (5)	0.2500	0.232 (4)	0.075*
H4B	−0.148 (5)	0.2500	0.397 (4)	0.075*
C5	0.3819 (3)	0.2500	0.0475 (2)	0.0358 (5)

	U11	U22	U33	U12	U13	U23
Cl	0.0457 (4)	0.0544 (4)	0.0238 (4)	0.000	0.0025 (2)	0.000
O2	0.0359 (10)	0.0837 (14)	0.0345 (10)	0.000	0.0078 (7)	0.000
O1	0.0443 (11)	0.0932 (15)	0.0205 (9)	0.000	0.0023 (7)	0.000
N1	0.0335 (11)	0.0449 (12)	0.0238 (10)	0.000	−0.0002 (8)	0.000
C1	0.0303 (11)	0.0355 (12)	0.0211 (11)	0.000	−0.0004 (8)	0.000
C2	0.0439 (10)	0.0402 (10)	0.0373 (10)	0.0074 (8)	−0.0004 (8)	0.0024 (7)
C3	0.0497 (11)	0.0707 (14)	0.0412 (10)	0.0221 (10)	0.0052 (9)	−0.0058 (10)
C4	0.0386 (15)	0.105 (3)	0.0449 (17)	0.000	0.0076 (13)	0.000
C5	0.0385 (13)	0.0425 (13)	0.0262 (12)	0.000	0.0025 (10)	0.000

O2—C5	1.201 (3)	C2—C3	1.516 (3)
O1—C5	1.322 (3)	C2—H2A	0.95 (2)
O1—H1	0.89 (4)	C2—H2B	0.95 (2)
N1—C1	1.504 (3)	C3—C4	1.505 (3)
N1—H1A	0.88 (2)	C3—H3A	0.97 (2)
N1—H1B	0.90 (3)	C3—H3B	0.98 (2)
C1—C5	1.524 (3)	C4—H4A	0.99 (3)
C1—C2	1.528 (2)	C4—H4B	1.05 (4)
C5—O1—H1	109 (2)	C4—C3—C2	111.85 (19)
C1—N1—H1A	110.2 (13)	C4—C3—H3A	107.9 (13)
C1—N1—H1B	114.0 (18)	C2—C3—H3A	109.9 (12)
H1A—N1—H1B	107.1 (16)	C4—C3—H3B	110.2 (13)
N1—C1—C5	105.28 (18)	C2—C3—H3B	108.4 (13)
N1—C1—C2	109.04 (12)	H3A—C3—H3B	108.5 (17)
C5—C1—C2	110.97 (12)	C3—C4—H4A	108.6 (10)
C3—C2—C1	112.64 (16)	C3—C4—H4B	114.6 (8)
C3—C2—H2A	113.8 (11)	H4A—C4—H4B	99 (3)
C1—C2—H2A	107.7 (12)	O2—C5—O1	125.2 (2)
C3—C2—H2B	108.3 (11)	O2—C5—C1	123.6 (2)
C1—C2—H2B	105.8 (12)	O1—C5—C1	111.2 (2)
H2A—C2—H2B	108.2 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···Cl	0.90 (3)	2.34 (3)	3.196 (2)	158 (2)
N1—H1A···Cli	0.88 (2)	2.58 (2)	3.3816 (13)	152.4 (17)
O1—H1···Clii	0.89 (4)	2.15 (4)	3.027 (2)	168 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯Cl	0.90 (3)	2.34 (3)	3.196 (2)	158 (2)
N1—H1A⋯Cli	0.88 (2)	2.58 (2)	3.3816 (13)	152.4 (17)
O1—H1⋯Clii	0.89 (4)	2.15 (4)	3.027 (2)	168 (3)

Symmetry codes: (i) ; (ii) .