2,6-Diethyl-anilinium perchlorate.

The asymmetric unit of the title mol-ecular salt, C(10)H(16)N(+)·ClO(4) (-), contains two cations and two anions. The atoms of one of the ethyl side chains of one of the cations are disordered over two sets of sites in a 0.531 (13):0.469 (13) ratio. In the crystal, the components are linked by N-H⋯O and bifurcated N-H⋯(O,O) hydrogen bonds and weaker C-H⋯O inter-actions, such that the organic cations alternate with the perchlorate anions, forming ribbons in the a-axis direction.

Related literature

For background to the physical properties and potential applications of mol­ecular salts, see: Czarnecki et al. (1994 ▶); Mylrajan & Srinivasan (1991 ▶); Toumi Akriche et al. (2010 ▶); Xiao et al. (2005 ▶). For the graph-set notation of hydrogen-bond networks, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C10H16N+·ClO4 −

M = 249.69

Monoclinic,

a = 15.105 (3) Å

b = 21.192 (5) Å

c = 7.718 (6) Å

β = 98.10 (3)°

V = 2446 (2) Å3

Z = 8

Ag Kα radiation

λ = 0.56085 Å

μ = 0.17 mm−1

T = 293 K

0.50 × 0.40 × 0.20 mm

Data collection

Enraf–Nonius TurboCAD-4 diffractometer

15750 measured reflections

11941 independent reflections

2954 reflections with I > 2σ(I)

R int = 0.052

2 standard reflections every 120 min intensity decay: 5%

Refinement

R[F 2 > 2σ(F 2)] = 0.089

wR(F 2) = 0.278

S = 0.91

11941 reflections

304 parameters

H-atom parameters not refined

Δρmax = 0.36 e Å−3

Δρmin = −0.36 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536810004654/hb5332sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810004654/hb5332Isup2.hkl

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

C10H16N+·ClO4−	F(000) = 1056
Mr = 249.69	Dx = 1.356 Mg m−3
Monoclinic, P21/c	Ag Kα radiation, λ = 0.56085 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 15.105 (3) Å	θ = 9–11°
b = 21.192 (5) Å	µ = 0.17 mm−1
c = 7.718 (6) Å	T = 293 K
β = 98.10 (3)°	Block, colourless
V = 2446 (2) Å3	0.50 × 0.40 × 0.20 mm
Z = 8

Enraf–Nonius TurboCAD-4 diffractometer	Rint = 0.052
Radiation source: fine-focus sealed tube	θmax = 28.0°, θmin = 2.2°
graphite	h = −25→5
non–profiled ω scans	k = −35→0
15750 measured reflections	l = −12→12
11941 independent reflections	2 standard reflections every 120 min
2954 reflections with I > 2σ(I)	intensity decay: 5%

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)] = 0.089	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.278	H-atom parameters not refined
S = 0.91	w = 1/[σ2(Fo2) + (0.1095P)2 + ] where P = (Fo2 + 2Fc2)/3
11941 reflections	(Δ/σ)max < 0.001
304 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	Occ. (<1)
C7A	−0.0545 (10)	0.6898 (8)	0.139 (3)	0.094 (7)	0.469 (13)
H7A1	0.0024	0.7060	0.1960	0.112*	0.469 (13)
H7A2	−0.0600	0.7012	0.0165	0.112*	0.469 (13)
C7B	−0.0813 (12)	0.6774 (8)	0.089 (2)	0.106 (6)	0.531 (13)
H7B1	−0.0280	0.7030	0.1180	0.127*	0.531 (13)
H7B2	−0.0885	0.6726	−0.0373	0.127*	0.531 (13)
C8A	−0.1146 (10)	0.7157 (9)	0.204 (3)	0.126 (4)	0.469 (13)
H8A1	−0.1124	0.7604	0.1839	0.188*	0.469 (13)
H8A2	−0.1072	0.7076	0.3273	0.188*	0.469 (13)
H8A3	−0.1713	0.6995	0.1504	0.188*	0.469 (13)
C8B	−0.1498 (9)	0.7177 (8)	0.116 (3)	0.126 (4)	0.531 (13)
H8B1	−0.1429	0.7570	0.0571	0.188*	0.531 (13)
H8B2	−0.1481	0.7251	0.2387	0.188*	0.531 (13)
H8B3	−0.2061	0.6990	0.0695	0.188*	0.531 (13)
N2	0.37636 (18)	0.68014 (13)	0.7366 (3)	0.0541 (7)
H2A	0.3312	0.6531	0.7121	0.081*
H2B	0.3754	0.7078	0.6497	0.081*
H2C	0.3709	0.7005	0.8355	0.081*
O3	0.1026 (2)	0.65755 (15)	0.8694 (4)	0.1012 (11)
O1	0.18825 (19)	0.63681 (13)	0.6498 (4)	0.0866 (9)
O7	0.3499 (2)	0.68975 (12)	0.0880 (3)	0.0791 (8)
N1	0.1070 (2)	0.63278 (14)	0.2448 (4)	0.0658 (8)
H1A	0.1561	0.6116	0.2870	0.099*
H1B	0.0970	0.6629	0.3201	0.099*
H1C	0.1141	0.6502	0.1428	0.099*
O2	0.1721 (2)	0.73912 (12)	0.7426 (5)	0.1005 (11)
O5	0.3253 (3)	0.66497 (17)	0.3658 (4)	0.1196 (14)
O8	0.4341 (2)	0.61129 (16)	0.2440 (6)	0.1222 (14)
O6	0.2856 (2)	0.59355 (16)	0.1434 (5)	0.1159 (12)
O4	0.0539 (2)	0.6843 (2)	0.5835 (5)	0.1218 (13)
Cl1	0.12968 (6)	0.68032 (4)	0.71443 (11)	0.0502 (2)
Cl2	0.35009 (6)	0.63848 (4)	0.21107 (12)	0.0580 (3)
C1	0.0299 (2)	0.58913 (16)	0.2194 (4)	0.0544 (9)
C3	−0.0302 (3)	0.48757 (18)	0.2325 (5)	0.0674 (11)
H3	−0.0236	0.4448	0.2587	0.081*
C2	0.0446 (3)	0.52653 (16)	0.2615 (4)	0.0562 (9)
C4	−0.1126 (3)	0.5099 (2)	0.1672 (5)	0.0786 (12)
H4	−0.1612	0.4825	0.1497	0.094*
C6	−0.0529 (3)	0.6145 (2)	0.1543 (6)	0.0713 (11)
C9	0.1350 (3)	0.50228 (19)	0.3346 (5)	0.0723 (11)
H9A	0.1554	0.5253	0.4414	0.087*
H9B	0.1758	0.5118	0.2518	0.087*
C10	0.1413 (3)	0.43215 (19)	0.3754 (6)	0.0896 (14)
H10A	0.2019	0.4216	0.4210	0.134*
H10B	0.1231	0.4085	0.2703	0.134*
H10C	0.1030	0.4221	0.4606	0.134*
C5	−0.1239 (3)	0.5723 (2)	0.1274 (6)	0.0850 (13)
H5	−0.1804	0.5869	0.0813	0.102*
C11	0.4615 (2)	0.64544 (17)	0.7574 (4)	0.0548 (9)
C16	0.5406 (3)	0.6799 (2)	0.7952 (5)	0.0634 (10)
C12	0.4577 (3)	0.58089 (18)	0.7432 (5)	0.0647 (10)
C20	0.3702 (4)	0.4774 (3)	0.7116 (8)	0.125 (2)
H20A	0.3098	0.4624	0.6854	0.187*
H20B	0.3956	0.4630	0.8258	0.187*
H20C	0.4049	0.4616	0.6260	0.187*
C13	0.5396 (3)	0.5487 (2)	0.7667 (6)	0.0885 (14)
H13	0.5405	0.5049	0.7598	0.106*
C19	0.3704 (3)	0.5457 (2)	0.7082 (7)	0.0876 (14)
H19A	0.3333	0.5600	0.7930	0.105*
H19B	0.3411	0.5587	0.5938	0.105*
C17	0.5385 (3)	0.7511 (2)	0.8118 (6)	0.0765 (11)
H17A	0.5014	0.7616	0.9005	0.092*
H17B	0.5093	0.7682	0.7017	0.092*
C15	0.6199 (3)	0.6456 (3)	0.8166 (6)	0.0883 (14)
H15	0.6745	0.6663	0.8425	0.106*
C14	0.6174 (3)	0.5811 (3)	0.7994 (7)	0.0945 (15)
H14	0.6710	0.5589	0.8106	0.113*
C18	0.6274 (4)	0.7845 (3)	0.8577 (8)	0.120 (2)
H18A	0.6176	0.8292	0.8628	0.180*
H18B	0.6649	0.7755	0.7700	0.180*
H18C	0.6562	0.7699	0.9694	0.180*

	U11	U22	U33	U12	U13	U23
C7A	0.044 (6)	0.062 (9)	0.168 (16)	0.000 (6)	−0.007 (7)	0.039 (9)
C7B	0.119 (14)	0.088 (8)	0.130 (11)	−0.023 (9)	0.083 (11)	−0.023 (8)
C8A	0.050 (8)	0.135 (6)	0.187 (16)	0.045 (7)	−0.002 (6)	0.010 (9)
C8B	0.050 (8)	0.135 (6)	0.187 (16)	0.045 (7)	−0.002 (6)	0.010 (9)
N2	0.0530 (17)	0.0584 (16)	0.0511 (16)	0.0024 (14)	0.0081 (14)	−0.0052 (13)
O3	0.146 (3)	0.103 (2)	0.0636 (17)	−0.043 (2)	0.0447 (19)	−0.0017 (16)
O1	0.0757 (19)	0.0764 (18)	0.114 (2)	0.0053 (15)	0.0331 (18)	−0.0259 (16)
O7	0.107 (2)	0.0746 (17)	0.0590 (15)	−0.0023 (16)	0.0237 (16)	0.0112 (13)
N1	0.077 (2)	0.0641 (19)	0.0620 (18)	−0.0194 (16)	0.0293 (16)	−0.0043 (14)
O2	0.128 (3)	0.0523 (16)	0.129 (3)	−0.0247 (17)	0.044 (2)	−0.0107 (16)
O5	0.181 (4)	0.136 (3)	0.0490 (16)	0.062 (3)	0.041 (2)	0.0098 (17)
O8	0.073 (2)	0.082 (2)	0.216 (4)	0.0294 (18)	0.034 (2)	0.020 (2)
O6	0.108 (3)	0.091 (2)	0.149 (3)	−0.036 (2)	0.022 (2)	−0.002 (2)
O4	0.083 (2)	0.165 (3)	0.107 (3)	0.030 (2)	−0.020 (2)	−0.002 (2)
Cl1	0.0526 (5)	0.0464 (4)	0.0535 (5)	−0.0003 (4)	0.0142 (4)	−0.0012 (4)
Cl2	0.0594 (6)	0.0571 (5)	0.0608 (5)	0.0063 (5)	0.0198 (4)	0.0041 (4)
C1	0.062 (2)	0.057 (2)	0.0494 (18)	−0.0151 (18)	0.0236 (17)	−0.0073 (15)
C3	0.086 (3)	0.056 (2)	0.064 (2)	−0.022 (2)	0.021 (2)	−0.0045 (17)
C2	0.072 (3)	0.055 (2)	0.0449 (18)	−0.0150 (18)	0.0206 (18)	−0.0058 (15)
C4	0.076 (3)	0.091 (3)	0.071 (3)	−0.033 (3)	0.017 (2)	0.001 (2)
C6	0.076 (3)	0.068 (3)	0.078 (3)	−0.004 (2)	0.036 (2)	0.009 (2)
C9	0.076 (3)	0.072 (3)	0.071 (3)	−0.010 (2)	0.017 (2)	0.004 (2)
C10	0.104 (4)	0.075 (3)	0.089 (3)	0.004 (3)	0.012 (3)	0.012 (2)
C5	0.065 (3)	0.111 (4)	0.082 (3)	−0.006 (3)	0.020 (2)	0.013 (3)
C11	0.060 (2)	0.067 (2)	0.0380 (17)	0.0130 (19)	0.0068 (16)	−0.0003 (15)
C16	0.058 (2)	0.079 (3)	0.053 (2)	0.007 (2)	0.0057 (18)	−0.0018 (18)
C12	0.068 (3)	0.065 (2)	0.062 (2)	0.009 (2)	0.009 (2)	0.0027 (18)
C20	0.101 (4)	0.105 (4)	0.163 (6)	0.001 (3)	−0.001 (4)	0.017 (4)
C13	0.082 (3)	0.075 (3)	0.110 (4)	0.025 (3)	0.020 (3)	0.007 (3)
C19	0.077 (3)	0.063 (3)	0.121 (4)	0.010 (2)	0.006 (3)	−0.002 (2)
C17	0.060 (3)	0.090 (3)	0.078 (3)	−0.007 (2)	0.007 (2)	−0.013 (2)
C15	0.057 (3)	0.114 (4)	0.091 (3)	0.009 (3)	−0.001 (2)	0.004 (3)
C14	0.066 (3)	0.100 (4)	0.119 (4)	0.024 (3)	0.017 (3)	0.009 (3)
C18	0.095 (4)	0.118 (4)	0.145 (5)	−0.031 (3)	0.010 (4)	−0.024 (4)

C7A—C8A	1.22 (3)	C2—C9	1.493 (5)
C7A—C6	1.599 (17)	C4—C5	1.363 (6)
C7A—H7A1	0.9700	C4—H4	0.9300
C7A—H7A2	0.9700	C6—C5	1.390 (6)
C7B—C8B	1.38 (2)	C9—C10	1.520 (5)
C7B—C6	1.468 (19)	C9—H9A	0.9700
C7B—H7B1	0.9700	C9—H9B	0.9700
C7B—H7B2	0.9700	C10—H10A	0.9600
C8A—H8A1	0.9600	C10—H10B	0.9600
C8A—H8A2	0.9600	C10—H10C	0.9600
C8A—H8A3	0.9600	C5—H5	0.9300
C8B—H8B1	0.9600	C11—C12	1.373 (5)
C8B—H8B2	0.9600	C11—C16	1.395 (5)
C8B—H8B3	0.9600	C16—C15	1.392 (6)
N2—C11	1.471 (4)	C16—C17	1.515 (6)
N2—H2A	0.8900	C12—C13	1.402 (5)
N2—H2B	0.8900	C12—C19	1.506 (6)
N2—H2C	0.8900	C20—C19	1.446 (6)
O3—Cl1	1.404 (3)	C20—H20A	0.9600
O1—Cl1	1.416 (3)	C20—H20B	0.9600
O7—Cl2	1.443 (3)	C20—H20C	0.9600
N1—C1	1.478 (4)	C13—C14	1.354 (6)
N1—H1A	0.8900	C13—H13	0.9300
N1—H1B	0.8900	C19—H19A	0.9700
N1—H1C	0.8900	C19—H19B	0.9700
O2—Cl1	1.404 (3)	C17—C18	1.515 (6)
O5—Cl2	1.417 (3)	C17—H17A	0.9700
O8—Cl2	1.385 (3)	C17—H17B	0.9700
O6—Cl2	1.409 (3)	C15—C14	1.374 (6)
O4—Cl1	1.418 (3)	C15—H15	0.9300
C1—C2	1.376 (5)	C14—H14	0.9300
C1—C6	1.389 (5)	C18—H18A	0.9600
C3—C4	1.360 (6)	C18—H18B	0.9600
C3—C2	1.391 (5)	C18—H18C	0.9600
C3—H3	0.9300
C8A—C7A—C6	115.0 (16)	C5—C6—C7B	110.6 (8)
C8A—C7A—H7A1	108.5	C1—C6—C7A	114.6 (6)
C6—C7A—H7A1	108.5	C5—C6—C7A	128.9 (7)
C8A—C7A—H7A2	108.5	C7B—C6—C7A	21.4 (10)
C6—C7A—H7A2	108.5	C2—C9—C10	116.3 (4)
H7A1—C7A—H7A2	107.5	C2—C9—H9A	108.2
C8B—C7B—C6	134.4 (14)	C10—C9—H9A	108.2
C8B—C7B—H7B1	103.6	C2—C9—H9B	108.2
C6—C7B—H7B1	103.6	C10—C9—H9B	108.2
C8B—C7B—H7B2	103.6	H9A—C9—H9B	107.4
C6—C7B—H7B2	103.6	C9—C10—H10A	109.5
H7B1—C7B—H7B2	105.3	C9—C10—H10B	109.5
C7A—C8A—H8A1	109.5	H10A—C10—H10B	109.5
C7A—C8A—H8A2	109.5	C9—C10—H10C	109.5
H8A1—C8A—H8A2	109.5	H10A—C10—H10C	109.5
C7A—C8A—H8A3	109.5	H10B—C10—H10C	109.5
H8A1—C8A—H8A3	109.5	C4—C5—C6	121.4 (5)
H8A2—C8A—H8A3	109.5	C4—C5—H5	119.3
C7B—C8B—H8B1	109.5	C6—C5—H5	119.3
C7B—C8B—H8B2	109.5	C12—C11—C16	124.3 (4)
H8B1—C8B—H8B2	109.5	C12—C11—N2	117.6 (3)
C7B—C8B—H8B3	109.5	C16—C11—N2	118.1 (3)
H8B1—C8B—H8B3	109.5	C15—C16—C11	116.7 (4)
H8B2—C8B—H8B3	109.5	C15—C16—C17	122.5 (4)
C11—N2—H2A	109.5	C11—C16—C17	120.8 (3)
C11—N2—H2B	109.5	C11—C12—C13	116.7 (4)
H2A—N2—H2B	109.5	C11—C12—C19	122.3 (4)
C11—N2—H2C	109.5	C13—C12—C19	121.0 (4)
H2A—N2—H2C	109.5	C19—C20—H20A	109.5
H2B—N2—H2C	109.5	C19—C20—H20B	109.5
C1—N1—H1A	109.5	H20A—C20—H20B	109.5
C1—N1—H1B	109.5	C19—C20—H20C	109.5
H1A—N1—H1B	109.5	H20A—C20—H20C	109.5
C1—N1—H1C	109.5	H20B—C20—H20C	109.5
H1A—N1—H1C	109.5	C14—C13—C12	120.3 (4)
H1B—N1—H1C	109.5	C14—C13—H13	119.9
O3—Cl1—O2	110.8 (2)	C12—C13—H13	119.9
O3—Cl1—O1	110.4 (2)	C20—C19—C12	119.8 (4)
O2—Cl1—O1	109.79 (19)	C20—C19—H19A	107.4
O3—Cl1—O4	108.9 (2)	C12—C19—H19A	107.4
O2—Cl1—O4	111.2 (2)	C20—C19—H19B	107.4
O1—Cl1—O4	105.6 (2)	C12—C19—H19B	107.4
O8—Cl2—O6	110.8 (2)	H19A—C19—H19B	106.9
O8—Cl2—O5	110.8 (3)	C16—C17—C18	117.2 (4)
O6—Cl2—O5	109.2 (2)	C16—C17—H17A	108.0
O8—Cl2—O7	110.6 (2)	C18—C17—H17A	108.0
O6—Cl2—O7	109.1 (2)	C16—C17—H17B	108.0
O5—Cl2—O7	106.27 (19)	C18—C17—H17B	108.0
C2—C1—C6	124.4 (3)	H17A—C17—H17B	107.2
C2—C1—N1	118.4 (3)	C14—C15—C16	119.7 (5)
C6—C1—N1	117.3 (3)	C14—C15—H15	120.1
C4—C3—C2	122.2 (4)	C16—C15—H15	120.1
C4—C3—H3	118.9	C13—C14—C15	122.3 (5)
C2—C3—H3	118.9	C13—C14—H14	118.8
C1—C2—C3	115.8 (4)	C15—C14—H14	118.8
C1—C2—C9	121.9 (3)	C17—C18—H18A	109.5
C3—C2—C9	122.3 (3)	C17—C18—H18B	109.5
C3—C4—C5	120.0 (4)	H18A—C18—H18B	109.5
C3—C4—H4	120.0	C17—C18—H18C	109.5
C5—C4—H4	120.0	H18A—C18—H18C	109.5
C1—C6—C5	116.2 (4)	H18B—C18—H18C	109.5
C1—C6—C7B	132.9 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O6	0.89	2.41	3.029 (4)	127
N1—H1B···O4	0.89	2.27	3.043 (5)	146
N1—H1B···O2i	0.89	2.48	2.889 (4)	109
N1—H1C···O3ii	0.89	2.10	2.935 (4)	157
N1—H1C···O2i	0.89	2.58	2.889 (4)	101
N2—H2A···O1	0.89	2.17	2.971 (4)	149
N2—H2B···O5	0.89	2.39	2.875 (4)	114
N2—H2B···O7iii	0.89	2.24	2.991 (4)	141
N2—H2C···O7iv	0.89	2.03	2.805 (3)	144
C3—H3···O3v	0.93	2.60	3.321 (5)	134
C13—H13···O8vi	0.93	2.49	3.418 (6)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O6	0.89	2.41	3.029 (4)	127
N1—H1B⋯O4	0.89	2.27	3.043 (5)	146
N1—H1B⋯O2i	0.89	2.48	2.889 (4)	109
N1—H1C⋯O3ii	0.89	2.10	2.935 (4)	157
N1—H1C⋯O2i	0.89	2.58	2.889 (4)	101
N2—H2A⋯O1	0.89	2.17	2.971 (4)	149
N2—H2B⋯O5	0.89	2.39	2.875 (4)	114
N2—H2B⋯O7iii	0.89	2.24	2.991 (4)	141
N2—H2C⋯O7iv	0.89	2.03	2.805 (3)	144
C3—H3⋯O3v	0.93	2.60	3.321 (5)	134
C13—H13⋯O8vi	0.93	2.49	3.418 (6)	172

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