4-Methyl-anilinium perchlorate 18-crown-6 clathrate.

In the title compound, C(7)H(10)N(+)·ClO(4) (-)·C(12)H(24)O(6), the 4-methyl-anilinium cation inter-acts with an 18-crown-6 mol-ecule forming a rotator-stator-like structure through bifurcated N-H⋯(O,O) hydrogen bonds between the ammonium group of the cation and the O atoms of the crown ether mol-ecule. All three components of the structure possess mirror symmetry. The benzene ring is inclined to the mean plane of the crown ether molecule by 86.84 (8)°.

Related literature

The crystal structure of related 4-methyl­anilinium tetra­fluoro­borate 18-crown-6 clathrate has been reported by Ge & Zhao (2010 ▶).

Experimental

Crystal data

C7H10N+·ClO4 −·C12H24O6

M = 471.92

Orthorhombic,

a = 15.510 (3) Å

b = 11.717 (2) Å

c = 13.014 (3) Å

V = 2365.0 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 293 K

0.27 × 0.26 × 0.23 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.944, T max = 0.952

23471 measured reflections

2843 independent reflections

2051 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.131

S = 1.04

2843 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrystalClear (Rigaku, 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811053992/cv5196sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811053992/cv5196Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811053992/cv5196Isup3.cml

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

C7H10N+·ClO4−·C12H24O6	F(000) = 1008
Mr = 471.92	Dx = 1.325 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	θ = 3.1–27.8°
a = 15.510 (3) Å	µ = 0.21 mm−1
b = 11.717 (2) Å	T = 293 K
c = 13.014 (3) Å	Block, colourless
V = 2365.0 (8) Å3	0.27 × 0.26 × 0.23 mm
Z = 4

Rigaku Mercury2 diffractometer	2843 independent reflections
Radiation source: fine-focus sealed tube	2051 reflections with I > 2σ(I)
graphite	Rint = 0.056
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.1°
CCD_Profile_fitting scans	h = −20→19
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −15→15
Tmin = 0.944, Tmax = 0.952	l = −16→16
23471 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0508P)2 + 0.9055P] where P = (Fo2 + 2Fc2)/3
2843 reflections	(Δ/σ)max < 0.001
156 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.29 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	Occ. (<1)
Cl1	0.39923 (4)	0.2500	0.29294 (6)	0.0499 (2)
O9	0.48479 (14)	0.2500	0.33632 (19)	0.0668 (6)
O10	0.38749 (12)	0.14964 (16)	0.23197 (15)	0.0872 (6)
O8	0.33818 (15)	0.2500	0.37618 (19)	0.0764 (7)
O3	0.39105 (9)	0.03863 (11)	0.71904 (11)	0.0521 (4)
O4	0.45688 (13)	0.2500	0.65171 (14)	0.0500 (5)
N1	0.29743 (14)	0.2500	0.77156 (16)	0.0419 (5)
H1A	0.2845	0.2166	0.8310	0.063*	0.50
H1B	0.3141	0.3216	0.7830	0.063*	0.50
H1C	0.3400	0.2118	0.7412	0.063*	0.50
O2	0.29941 (9)	0.04793 (12)	0.90648 (11)	0.0584 (4)
O1	0.21558 (14)	0.2500	0.97086 (15)	0.0608 (6)
C13	0.22121 (16)	0.2500	0.70472 (18)	0.0392 (6)
C9	0.39753 (15)	−0.04759 (18)	0.79645 (17)	0.0588 (6)
H9A	0.4433	−0.0283	0.8442	0.071*
H9B	0.4114	−0.1203	0.7649	0.071*
C8	0.46909 (14)	0.04990 (18)	0.66202 (17)	0.0564 (5)
H8A	0.4795	−0.0190	0.6227	0.068*
H8B	0.5171	0.0608	0.7087	0.068*
C14	0.18536 (14)	0.14842 (18)	0.67484 (15)	0.0533 (5)
H14	0.2097	0.0797	0.6956	0.064*
C7	0.46218 (15)	0.14939 (18)	0.59148 (15)	0.0545 (5)
H7A	0.5123	0.1528	0.5470	0.065*
H7B	0.4112	0.1421	0.5488	0.065*
C10	0.31436 (15)	−0.05658 (18)	0.85247 (18)	0.0611 (6)
H10A	0.2678	−0.0705	0.8043	0.073*
H10B	0.3165	−0.1197	0.9006	0.073*
C11	0.22117 (15)	0.0464 (2)	0.9626 (2)	0.0705 (7)
H11A	0.2175	−0.0228	1.0032	0.085*
H11B	0.1726	0.0482	0.9158	0.085*
C12	0.21869 (16)	0.1486 (2)	1.03166 (17)	0.0720 (7)
H12A	0.1683	0.1448	1.0757	0.086*
H12B	0.2696	0.1497	1.0750	0.086*
C17	0.07397 (19)	0.2500	0.5819 (2)	0.0558 (8)
C18	0.11245 (14)	0.1491 (2)	0.61334 (16)	0.0598 (6)
H18	0.0887	0.0799	0.5926	0.072*
C19	−0.0071 (2)	0.2500	0.5175 (3)	0.0878 (12)
H19A	−0.0486	0.1992	0.5474	0.132*	0.50
H19B	0.0064	0.2250	0.4491	0.132*	0.50
H19C	−0.0305	0.3258	0.5150	0.132*	0.50

	U11	U22	U33	U12	U13	U23
Cl1	0.0481 (4)	0.0428 (4)	0.0587 (4)	0.000	0.0021 (3)	0.000
O9	0.0551 (13)	0.0592 (13)	0.0862 (16)	0.000	−0.0069 (12)	0.000
O10	0.0857 (13)	0.0753 (12)	0.1007 (13)	−0.0023 (10)	−0.0109 (11)	−0.0348 (11)
O8	0.0657 (15)	0.0856 (17)	0.0778 (16)	0.000	0.0166 (13)	0.000
O3	0.0547 (8)	0.0424 (7)	0.0593 (9)	0.0062 (6)	0.0008 (7)	0.0064 (6)
O4	0.0629 (12)	0.0435 (11)	0.0437 (10)	0.000	0.0081 (9)	0.000
N1	0.0443 (12)	0.0426 (12)	0.0388 (12)	0.000	0.0047 (10)	0.000
O2	0.0560 (9)	0.0527 (9)	0.0664 (9)	−0.0097 (7)	0.0087 (7)	0.0088 (7)
O1	0.0650 (13)	0.0781 (15)	0.0393 (11)	0.000	0.0077 (10)	0.000
C13	0.0397 (13)	0.0461 (14)	0.0319 (12)	0.000	0.0051 (11)	0.000
C9	0.0688 (14)	0.0412 (11)	0.0665 (14)	0.0059 (10)	−0.0085 (12)	0.0068 (10)
C8	0.0589 (12)	0.0497 (12)	0.0605 (13)	0.0122 (10)	0.0065 (11)	−0.0074 (10)
C14	0.0597 (12)	0.0468 (12)	0.0534 (12)	−0.0010 (10)	−0.0048 (10)	0.0000 (9)
C7	0.0610 (12)	0.0549 (13)	0.0477 (11)	0.0044 (10)	0.0069 (10)	−0.0079 (10)
C10	0.0699 (14)	0.0433 (12)	0.0700 (14)	−0.0104 (10)	−0.0115 (12)	0.0142 (10)
C11	0.0611 (14)	0.0783 (17)	0.0721 (16)	−0.0125 (12)	0.0103 (12)	0.0237 (14)
C12	0.0649 (14)	0.106 (2)	0.0453 (12)	−0.0048 (14)	0.0128 (11)	0.0184 (14)
C17	0.0428 (15)	0.082 (2)	0.0421 (15)	0.000	0.0020 (13)	0.000
C18	0.0607 (13)	0.0635 (14)	0.0550 (12)	−0.0145 (11)	−0.0021 (11)	−0.0045 (11)
C19	0.060 (2)	0.126 (4)	0.077 (3)	0.000	−0.016 (2)	0.000

Cl1—O10	1.4302 (17)	C8—C7	1.488 (3)
Cl1—O10i	1.4302 (17)	C8—H8A	0.9700
Cl1—O8	1.439 (2)	C8—H8B	0.9700
Cl1—O9	1.442 (2)	C14—C18	1.385 (3)
O3—C8	1.426 (2)	C14—H14	0.9300
O3—C9	1.430 (2)	C7—H7A	0.9700
O4—C7i	1.418 (2)	C7—H7B	0.9700
O4—C7	1.418 (2)	C10—H10A	0.9700
N1—C13	1.468 (3)	C10—H10B	0.9700
N1—H1A	0.8900	C11—C12	1.497 (3)
N1—H1B	0.8900	C11—H11A	0.9700
N1—H1C	0.8900	C11—H11B	0.9700
O2—C11	1.417 (3)	C12—H12A	0.9700
O2—C10	1.431 (3)	C12—H12B	0.9700
O1—C12i	1.428 (3)	C17—C18i	1.386 (3)
O1—C12	1.428 (3)	C17—C18	1.386 (3)
C13—C14	1.370 (2)	C17—C19	1.511 (4)
C13—C14i	1.370 (2)	C18—H18	0.9300
C9—C10	1.485 (3)	C19—H19A	0.9600
C9—H9A	0.9700	C19—H19B	0.9600
C9—H9B	0.9700	C19—H19C	0.9600
O10—Cl1—O10i	110.61 (17)	O4—C7—H7A	110.0
O10—Cl1—O8	109.50 (10)	C8—C7—H7A	110.0
O10i—Cl1—O8	109.50 (10)	O4—C7—H7B	110.0
O10—Cl1—O9	109.54 (9)	C8—C7—H7B	110.0
O10i—Cl1—O9	109.54 (9)	H7A—C7—H7B	108.4
O8—Cl1—O9	108.11 (15)	O2—C10—C9	108.74 (17)
C8—O3—C9	111.86 (15)	O2—C10—H10A	109.9
C7i—O4—C7	112.5 (2)	C9—C10—H10A	109.9
C13—N1—H1A	109.5	O2—C10—H10B	109.9
C13—N1—H1B	109.5	C9—C10—H10B	109.9
H1A—N1—H1B	109.5	H10A—C10—H10B	108.3
C13—N1—H1C	109.5	O2—C11—C12	108.77 (19)
H1A—N1—H1C	109.5	O2—C11—H11A	109.9
H1B—N1—H1C	109.5	C12—C11—H11A	109.9
C11—O2—C10	112.44 (17)	O2—C11—H11B	109.9
C12i—O1—C12	112.6 (2)	C12—C11—H11B	109.9
C14—C13—C14i	120.6 (3)	H11A—C11—H11B	108.3
C14—C13—N1	119.68 (13)	O1—C12—C11	109.48 (17)
C14i—C13—N1	119.68 (13)	O1—C12—H12A	109.8
O3—C9—C10	109.56 (17)	C11—C12—H12A	109.8
O3—C9—H9A	109.8	O1—C12—H12B	109.8
C10—C9—H9A	109.8	C11—C12—H12B	109.8
O3—C9—H9B	109.8	H12A—C12—H12B	108.2
C10—C9—H9B	109.8	C18i—C17—C18	117.1 (3)
H9A—C9—H9B	108.2	C18i—C17—C19	121.45 (14)
O3—C8—C7	109.42 (16)	C18—C17—C19	121.45 (14)
O3—C8—H8A	109.8	C14—C18—C17	121.8 (2)
C7—C8—H8A	109.8	C14—C18—H18	119.1
O3—C8—H8B	109.8	C17—C18—H18	119.1
C7—C8—H8B	109.8	C17—C19—H19A	109.5
H8A—C8—H8B	108.2	C17—C19—H19B	109.5
C13—C14—C18	119.4 (2)	H19A—C19—H19B	109.5
C13—C14—H14	120.3	C17—C19—H19C	109.5
C18—C14—H14	120.3	H19A—C19—H19C	109.5
O4—C7—C8	108.33 (16)	H19B—C19—H19C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O2i	0.89	2.23	2.9477 (19)	138.
N1—H1B···O3i	0.89	2.19	2.9511 (18)	143.
N1—H1C···O4	0.89	2.20	2.924 (3)	138.
N1—H1C···O3	0.89	2.20	2.9511 (18)	142.
N1—H1A···O2	0.89	2.22	2.9477 (19)	139.
N1—H1A···O1	0.89	2.15	2.888 (3)	140.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O2i	0.89	2.23	2.9477 (19)	138
N1—H1B⋯O3i	0.89	2.19	2.9511 (18)	143
N1—H1C⋯O4	0.89	2.20	2.924 (3)	138
N1—H1C⋯O3	0.89	2.20	2.9511 (18)	142
N1—H1A⋯O2	0.89	2.22	2.9477 (19)	139
N1—H1A⋯O1	0.89	2.15	2.888 (3)	140

Symmetry code: (i) .