N-Cyclo-hexyl-cyclo-hexa-naminium chloride.

In the title salt, C(12)H(24)N(+)·Cl(-), both cyclo-hexyl rings adopt chair conformations and the NH(2) unit is situated in the equatorial position with respect to the rings in the cation. The large C-N-C bond angle [117.99 (14)°] in the cation is a result of linking two bulky cyclo-hexyl rings to the N atom. The aminium H atoms are involved in inter-molecular N-H⋯Cl hydrogen bonds, forming an infinite zigzag chain parallel to the c axis. The crystal studied was a racemic twin with a twin fraction of 0.28 (18).

Related literature

For related structures, see: Gholivand & Pourayoubi (2004 ▶); Pourayoubi & Negari (2010 ▶).

Experimental

Crystal data

C12H24N+·Cl−

M = 217.77

Orthorhombic,

a = 40.0268 (19) Å

b = 23.1726 (10) Å

c = 5.3463 (2) Å

V = 4958.8 (4) Å3

Z = 16

Mo Kα radiation

μ = 0.27 mm−1

T = 120 K

0.30 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Sapphire2 diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.886, T max = 1.000

13243 measured reflections

1219 independent reflections

1096 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.057

S = 1.00

1219 reflections

136 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.11 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811000857/pv2369sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000857/pv2369Isup2.hkl

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

C12H24N+·Cl−	F(000) = 1920
Mr = 217.77	Dx = 1.167 Mg m−3
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 6909 reflections
a = 40.0268 (19) Å	θ = 2.8–27.3°
b = 23.1726 (10) Å	µ = 0.27 mm−1
c = 5.3463 (2) Å	T = 120 K
V = 4958.8 (4) Å3	Block, colorless
Z = 16	0.30 × 0.20 × 0.20 mm

Oxford Diffraction Xcalibur Sapphire2 diffractometer	1219 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1096 reflections with I > 2σ(I)
graphite	Rint = 0.032
Detector resolution: 8.4353 pixels mm-1	θmax = 25.0°, θmin = 3.5°
ω scans	h = −25→47
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −26→27
Tmin = 0.886, Tmax = 1.000	l = −6→6
13243 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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.057	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0378P)2] where P = (Fo2 + 2Fc2)/3
1219 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.30 e Å−3
1 restraint	Δρmin = −0.11 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	0.100648 (13)	0.19484 (2)	0.28104 (17)	0.02112 (15)
N1	0.10617 (4)	0.26694 (6)	0.7818 (5)	0.0166 (4)
C1	0.14111 (5)	0.29218 (8)	0.7797 (5)	0.0161 (4)
H1B	0.1433	0.3186	0.6328	0.019*
C2	0.16565 (5)	0.24213 (9)	0.7477 (5)	0.0228 (5)
H2A	0.1611	0.2221	0.5877	0.027*
H2B	0.1625	0.2140	0.8852	0.027*
C3	0.20173 (5)	0.26402 (10)	0.7495 (5)	0.0258 (5)
H3A	0.2172	0.2309	0.7360	0.031*
H3B	0.2054	0.2894	0.6032	0.031*
C4	0.20916 (5)	0.29750 (9)	0.9898 (5)	0.0237 (6)
H4A	0.2074	0.2713	1.1354	0.028*
H4B	0.2322	0.3128	0.9837	0.028*
C5	0.18455 (5)	0.34732 (8)	1.0204 (6)	0.0227 (5)
H5A	0.1879	0.3753	0.8828	0.027*
H5B	0.1891	0.3674	1.1802	0.027*
C6	0.14823 (5)	0.32636 (8)	1.0181 (6)	0.0207 (5)
H6A	0.1441	0.3016	1.1660	0.025*
H6B	0.1330	0.3599	1.0276	0.025*
C7	0.07713 (5)	0.30801 (8)	0.7845 (6)	0.0169 (4)
H7A	0.0804	0.3363	0.9238	0.020*
C8	0.04529 (5)	0.27365 (9)	0.8342 (5)	0.0219 (5)
H8A	0.0471	0.2538	0.9977	0.026*
H8B	0.0425	0.2439	0.7031	0.026*
C9	0.01485 (6)	0.31357 (11)	0.8354 (5)	0.0277 (6)
H9A	−0.0056	0.2903	0.8594	0.033*
H9B	0.0166	0.3408	0.9774	0.033*
C10	0.01206 (6)	0.34760 (10)	0.5914 (5)	0.0262 (6)
H10A	−0.0068	0.3751	0.6034	0.031*
H10B	0.0074	0.3207	0.4518	0.031*
C11	0.04427 (5)	0.38076 (8)	0.5367 (5)	0.0224 (5)
H11A	0.0473	0.4112	0.6644	0.027*
H11B	0.0424	0.3998	0.3715	0.027*
C12	0.07490 (5)	0.34125 (8)	0.5370 (5)	0.0196 (5)
H12A	0.0954	0.3646	0.5138	0.024*
H12B	0.0733	0.3136	0.3962	0.024*
H1N	0.1053 (6)	0.2468 (10)	0.920 (5)	0.012 (7)*
H2N	0.1029 (6)	0.2391 (12)	0.634 (6)	0.040 (9)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0307 (3)	0.0149 (2)	0.0178 (2)	0.0004 (2)	−0.0032 (3)	0.0000 (2)
N1	0.0183 (11)	0.0159 (8)	0.0155 (8)	0.0013 (7)	−0.0006 (9)	0.0034 (10)
C1	0.0125 (10)	0.0191 (10)	0.0169 (10)	−0.0010 (8)	−0.0012 (12)	0.0001 (11)
C2	0.0209 (13)	0.0225 (11)	0.0250 (13)	0.0037 (10)	−0.0036 (11)	−0.0085 (10)
C3	0.0159 (13)	0.0342 (12)	0.0274 (13)	0.0057 (10)	−0.0037 (12)	−0.0105 (12)
C4	0.0171 (13)	0.0275 (12)	0.0265 (13)	−0.0003 (10)	−0.0046 (12)	−0.0067 (10)
C5	0.0184 (13)	0.0217 (10)	0.0280 (12)	−0.0004 (9)	−0.0064 (13)	−0.0072 (13)
C6	0.0191 (12)	0.0195 (10)	0.0235 (11)	0.0022 (10)	−0.0002 (11)	−0.0019 (12)
C7	0.0164 (11)	0.0172 (9)	0.0171 (9)	0.0033 (9)	−0.0024 (13)	−0.0034 (10)
C8	0.0205 (13)	0.0249 (12)	0.0203 (13)	−0.0018 (10)	−0.0001 (10)	0.0081 (9)
C9	0.0170 (13)	0.0374 (14)	0.0288 (16)	−0.0005 (11)	0.0014 (10)	0.0076 (11)
C10	0.0210 (14)	0.0277 (12)	0.0298 (15)	0.0037 (11)	−0.0044 (11)	0.0041 (10)
C11	0.0209 (13)	0.0184 (10)	0.0281 (12)	0.0008 (9)	−0.0028 (13)	0.0017 (11)
C12	0.0187 (13)	0.0162 (10)	0.0240 (11)	−0.0003 (9)	0.0003 (12)	0.0051 (11)

N1—C7	1.502 (2)	C6—H6A	0.9900
N1—C1	1.516 (2)	C6—H6B	0.9900
N1—H1N	0.87 (2)	C7—C8	1.526 (3)
N1—H2N	1.03 (3)	C7—C12	1.534 (4)
C1—C6	1.527 (4)	C7—H7A	1.0000
C1—C2	1.529 (3)	C8—C9	1.530 (3)
C1—H1B	1.0000	C8—H8A	0.9900
C2—C3	1.531 (3)	C8—H8B	0.9900
C2—H2A	0.9900	C9—C10	1.529 (3)
C2—H2B	0.9900	C9—H9A	0.9900
C3—C4	1.530 (3)	C9—H9B	0.9900
C3—H3A	0.9900	C10—C11	1.529 (3)
C3—H3B	0.9900	C10—H10A	0.9900
C4—C5	1.526 (3)	C10—H10B	0.9900
C4—H4A	0.9900	C11—C12	1.530 (3)
C4—H4B	0.9900	C11—H11A	0.9900
C5—C6	1.533 (3)	C11—H11B	0.9900
C5—H5A	0.9900	C12—H12A	0.9900
C5—H5B	0.9900	C12—H12B	0.9900
C7—N1—C1	117.99 (14)	C1—C6—H6B	109.6
C7—N1—H1N	107.4 (15)	C5—C6—H6B	109.6
C1—N1—H1N	104.4 (15)	H6A—C6—H6B	108.1
C7—N1—H2N	107.9 (15)	N1—C7—C8	108.49 (15)
C1—N1—H2N	110.7 (14)	N1—C7—C12	110.8 (2)
H1N—N1—H2N	108.0 (17)	C8—C7—C12	111.32 (19)
N1—C1—C6	111.49 (19)	N1—C7—H7A	108.7
N1—C1—C2	107.50 (15)	C8—C7—H7A	108.7
C6—C1—C2	111.50 (18)	C12—C7—H7A	108.7
N1—C1—H1B	108.8	C7—C8—C9	110.51 (17)
C6—C1—H1B	108.8	C7—C8—H8A	109.5
C2—C1—H1B	108.8	C9—C8—H8A	109.5
C1—C2—C3	110.73 (17)	C7—C8—H8B	109.5
C1—C2—H2A	109.5	C9—C8—H8B	109.5
C3—C2—H2A	109.5	H8A—C8—H8B	108.1
C1—C2—H2B	109.5	C10—C9—C8	111.50 (19)
C3—C2—H2B	109.5	C10—C9—H9A	109.3
H2A—C2—H2B	108.1	C8—C9—H9A	109.3
C4—C3—C2	110.89 (19)	C10—C9—H9B	109.3
C4—C3—H3A	109.5	C8—C9—H9B	109.3
C2—C3—H3A	109.5	H9A—C9—H9B	108.0
C4—C3—H3B	109.5	C9—C10—C11	111.2 (2)
C2—C3—H3B	109.5	C9—C10—H10A	109.4
H3A—C3—H3B	108.0	C11—C10—H10A	109.4
C5—C4—C3	110.37 (19)	C9—C10—H10B	109.4
C5—C4—H4A	109.6	C11—C10—H10B	109.4
C3—C4—H4A	109.6	H10A—C10—H10B	108.0
C5—C4—H4B	109.6	C10—C11—C12	112.01 (16)
C3—C4—H4B	109.6	C10—C11—H11A	109.2
H4A—C4—H4B	108.1	C12—C11—H11A	109.2
C4—C5—C6	111.81 (16)	C10—C11—H11B	109.2
C4—C5—H5A	109.3	C12—C11—H11B	109.2
C6—C5—H5A	109.3	H11A—C11—H11B	107.9
C4—C5—H5B	109.3	C11—C12—C7	110.37 (19)
C6—C5—H5B	109.3	C11—C12—H12A	109.6
H5A—C5—H5B	107.9	C7—C12—H12A	109.6
C1—C6—C5	110.4 (2)	C11—C12—H12B	109.6
C1—C6—H6A	109.6	C7—C12—H12B	109.6
C5—C6—H6A	109.6	H12A—C12—H12B	108.1
C7—N1—C1—C6	63.7 (3)	C1—N1—C7—C8	−169.8 (2)
C7—N1—C1—C2	−173.8 (2)	C1—N1—C7—C12	67.7 (3)
N1—C1—C2—C3	−178.8 (2)	N1—C7—C8—C9	−179.26 (19)
C6—C1—C2—C3	−56.3 (3)	C12—C7—C8—C9	−57.1 (2)
C1—C2—C3—C4	56.7 (3)	C7—C8—C9—C10	56.2 (3)
C2—C3—C4—C5	−56.6 (2)	C8—C9—C10—C11	−54.7 (3)
C3—C4—C5—C6	56.5 (3)	C9—C10—C11—C12	54.4 (3)
N1—C1—C6—C5	175.55 (16)	C10—C11—C12—C7	−55.0 (3)
C2—C1—C6—C5	55.4 (2)	N1—C7—C12—C11	177.21 (16)
C4—C5—C6—C1	−55.7 (3)	C8—C7—C12—C11	56.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···Cl1i	0.87 (2)	2.28 (3)	3.157 (3)	178 (2)
N1—H2N···Cl1	1.03 (3)	2.15 (3)	3.163 (3)	168 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯Cl1i	0.87 (2)	2.28 (3)	3.157 (3)	178 (2)
N1—H2N⋯Cl1	1.03 (3)	2.15 (3)	3.163 (3)	168 (2)

Symmetry code: (i) .