trans-1-Hydroxy­cyclo­pentan-2-aminium chloride

The crystal structure of the title compound, C₅H₁₂NO⁺·Cl^-, is stabilized by ionic, hydrogen-bonding and hydro­phobic inter­actions. The cyclo­pentane ring of the trans-1-hydroxy­cyclo­pentan-2-aminium cation has a twist conformation, with both substituent groups in equatorial positions.

Key indicators

• Single-crystal X-ray study
• T = 103 K
• Mean [sigma](C-C) = 0.001 Å
• R factor = 0.031
• wR factor = 0.079
• Data-to-parameter ratio = 46.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) .        100 Ang.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          4

   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
   0 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: HKL-2000 (Otwinowski & Minor, 1997); cell refinement: HKL-2000; data reduction: HKL-2000; program(s) used to solve structure: HKL-3000SM (Minor et al., 2006) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: HKL-3000SM and SHELXL97 (Sheldrick, 1997); molecular graphics: HKL-3000SM, ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: HKL-3000SM.

trans 2-hydroxycyclopentan-2-aminium chloride

Crystal data

C5H12NO^+·Cl^−	F(000) = 296
Mr = 137.61	Dx = 1.364 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71074 Å
Hall symbol: -P 2ybc	Cell parameters from 40913 reflections
a = 10.130 (1) Å	θ = 3.1–30.5°
b = 8.736 (1) Å	µ = 0.48 mm^−1
c = 7.657 (1) Å	T = 103 K
β = 98.68 (1)°	Block, colourless
V = 669.86 (13) Å^3	0.45 × 0.2 × 0.08 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	5611 independent reflections
Radiation source: fine-focus sealed tube	4628 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
Detector resolution: 10 pixels mm^-1	θmax = 45.3°, θmin = 3.1°
ω scans with χ offset	h = −20→20
Absorption correction: multi-scan (Otwinowski et al., 2003)	k = −17→16
Tmin = 0.89, Tmax = 0.96	l = −15→15
40913 measured reflections

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)] = 0.031	Hydrogen site location: difference Fourier map
wR(F^2) = 0.079	All H-atom parameters refined
S = 0.90	w = 1/[σ^2(Fo^2) + (0.04P)^2 + 0.1217P] where P = (Fo^2 + 2Fc^2)/3
5611 reflections	(Δ/σ)max = 0.001
121 parameters	Δρmax = 0.45 e Å^−3
0 restraints	Δρmin = −0.28 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
Cl1	0.329449 (12)	0.464227 (13)	0.346563 (16)	0.01841 (3)
O1	0.40112 (4)	−0.19074 (4)	0.44317 (5)	0.01891 (6)
C1	0.29063 (5)	−0.12489 (5)	0.33185 (6)	0.01558 (6)
C2	0.29292 (5)	0.04865 (5)	0.35055 (6)	0.01566 (7)
N1	0.39427 (4)	0.12190 (5)	0.25553 (6)	0.01686 (6)
C5	0.15284 (5)	−0.16502 (6)	0.37641 (8)	0.02107 (8)
C3	0.14970 (5)	0.10065 (6)	0.27871 (9)	0.02456 (10)
C4	0.06349 (6)	−0.04561 (7)	0.26993 (10)	0.02525 (10)
H1N	0.3796 (10)	0.1017 (11)	0.1432 (13)	0.023 (2)*
H2	0.3164 (10)	0.0723 (12)	0.4736 (14)	0.025 (2)*
H1	0.2954 (9)	−0.1513 (10)	0.2097 (12)	0.0176 (19)*
H2N	0.4760 (11)	0.0919 (12)	0.2959 (14)	0.028 (2)*
H5B	0.1548 (10)	−0.1477 (12)	0.5005 (14)	0.028 (2)*
H3N	0.3869 (12)	0.2226 (14)	0.2681 (16)	0.036 (3)*
H3A	0.1454 (12)	0.1462 (15)	0.1632 (16)	0.041 (3)*
H1O	0.3908 (12)	−0.2830 (14)	0.4338 (16)	0.037 (3)*
H5A	0.1264 (11)	−0.2685 (12)	0.3461 (14)	0.029 (2)*
H4B	−0.0222 (13)	−0.0285 (13)	0.3129 (18)	0.041 (3)*
H4A	0.0416 (12)	−0.0783 (14)	0.1472 (16)	0.039 (3)*
H3B	0.1198 (13)	0.1797 (14)	0.3595 (18)	0.044 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.02081 (5)	0.01446 (4)	0.01945 (5)	−0.00055 (3)	0.00139 (4)	−0.00031 (3)
O1	0.01674 (13)	0.01407 (12)	0.02452 (16)	0.00152 (10)	−0.00145 (11)	0.00169 (11)
C1	0.01518 (15)	0.01306 (14)	0.01794 (16)	0.00010 (11)	0.00065 (12)	−0.00051 (11)
C2	0.01589 (16)	0.01313 (14)	0.01779 (16)	0.00029 (11)	0.00194 (12)	−0.00052 (11)
N1	0.01615 (14)	0.01441 (13)	0.01974 (15)	−0.00047 (11)	0.00172 (12)	0.00135 (11)
C5	0.01643 (17)	0.01762 (17)	0.0289 (2)	−0.00138 (14)	0.00241 (15)	0.00302 (16)
C3	0.01659 (18)	0.01730 (18)	0.0390 (3)	0.00266 (14)	0.00160 (18)	0.00376 (18)
C4	0.01616 (19)	0.0216 (2)	0.0362 (3)	0.00000 (15)	−0.00187 (18)	0.00338 (18)

Geometric parameters (Å, º)

O1—C1	1.4221 (6)	N1—H3N	0.889 (12)
O1—H1O	0.814 (12)	C5—C4	1.5328 (8)
C1—C2	1.5227 (7)	C5—H5B	0.960 (11)
C1—C5	1.5269 (7)	C5—H5A	0.962 (11)
C1—H1	0.971 (9)	C3—C4	1.5434 (8)
C2—N1	1.4893 (6)	C3—H3A	0.965 (12)
C2—C3	1.5405 (7)	C3—H3B	1.004 (13)
C2—H2	0.959 (10)	C4—H4B	0.985 (13)
N1—H1N	0.869 (10)	C4—H4A	0.976 (12)
N1—H2N	0.879 (11)
C1—O1—H1O	105.6 (9)	C1—C5—C4	102.19 (4)
O1—C1—C2	110.30 (4)	C1—C5—H5B	107.6 (6)
O1—C1—C5	115.88 (4)	C4—C5—H5B	110.0 (6)
C2—C1—C5	102.07 (4)	C1—C5—H5A	113.1 (6)
O1—C1—H1	109.4 (5)	C4—C5—H5A	113.0 (7)
C2—C1—H1	108.9 (5)	H5B—C5—H5A	110.6 (9)
C5—C1—H1	109.9 (5)	C2—C3—C4	105.53 (4)
N1—C2—C1	112.56 (4)	C2—C3—H3A	111.0 (7)
N1—C2—C3	112.36 (4)	C4—C3—H3A	110.7 (7)
C1—C2—C3	105.06 (4)	C2—C3—H3B	109.8 (7)
N1—C2—H2	107.5 (6)	C4—C3—H3B	112.0 (7)
C1—C2—H2	107.8 (6)	H3A—C3—H3B	107.7 (10)
C3—C2—H2	111.6 (6)	C5—C4—C3	104.80 (4)
C2—N1—H1N	111.7 (7)	C5—C4—H4B	113.9 (7)
C2—N1—H2N	112.5 (7)	C3—C4—H4B	112.4 (7)
H1N—N1—H2N	107.4 (9)	C5—C4—H4A	110.1 (7)
C2—N1—H3N	107.3 (7)	C3—C4—H4A	109.2 (7)
H1N—N1—H3N	107.6 (10)	H4B—C4—H4A	106.4 (10)
H2N—N1—H3N	110.3 (11)
O1—C1—C2—N1	76.33 (5)	C2—C1—C5—C4	45.30 (5)
C5—C1—C2—N1	−159.96 (4)	N1—C2—C3—C4	137.77 (5)
O1—C1—C2—C3	−161.10 (4)	C1—C2—C3—C4	15.06 (6)
C5—C1—C2—C3	−37.39 (5)	C1—C5—C4—C3	−35.99 (6)
O1—C1—C5—C4	165.17 (4)	C2—C3—C4—C5	12.99 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···Cl1^i	0.87 (1)	2.32 (1)	3.191 (1)	176 (1)
N1—H2N···O1^ii	0.88 (1)	2.35 (1)	2.922 (1)	123 (1)
N1—H2N···Cl1^iii	0.88 (1)	2.64 (1)	3.317 (1)	135 (1)
N1—H3N···Cl1	0.89 (1)	2.29 (1)	3.162 (1)	165 (1)
O1—H1O···Cl1^iv	0.81 (1)	2.36 (1)	3.162 (1)	167 (1)

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