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

In the title compound, C(6)H(7)IN(+)·ClO(4) (-)·C(12)H(24)O(6), the proton-ated 4-iodo-anilinium cation inter-acts with the 18-crown-6 through three N-H⋯O hydrogen bonds, forming a rotator-stator-like structure. The cation, anion and 18-crown-6 mol-ecule all have crystallographically imposed mirror symmetry.

Related literature

For the structure of a related 18-crown-6 clathrate, see: Ge & Zhao (2010 ▶). For ferroelectric properties, see: Fu et al. (2007 ▶); Ye et al.(2009 ▶); Zhang et al. (2009 ▶).

Experimental

Crystal data

C6H7IN+·ClO4 −·C12H24O6

M = 583.79

Orthorhombic,

a = 15.8805 (11) Å

b = 11.3878 (11) Å

c = 12.6754 (8) Å

V = 2292.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.57 mm−1

T = 93 K

0.40 × 0.30 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.575, T max = 0.731

24048 measured reflections

2755 independent reflections

2611 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.093

S = 1.11

2755 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.81 e Å−3

Δρmin = −0.65 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 datablocks I, global. DOI: 10.1107/S1600536811004260/rz2549sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004260/rz2549Isup2.hkl

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

C6H7IN+·ClO4−·C12H24O6	F(000) = 1184
Mr = 583.79	Dx = 1.692 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 17071 reflections
a = 15.8805 (11) Å	θ = 3.2–27.8°
b = 11.3878 (11) Å	µ = 1.57 mm−1
c = 12.6754 (8) Å	T = 93 K
V = 2292.3 (3) Å3	Prism, colourless
Z = 4	0.40 × 0.30 × 0.20 mm

Rigaku SCXmini diffractometer	2755 independent reflections
Radiation source: fine-focus sealed tube	2611 reflections with I > 2σ(I)
graphite	Rint = 0.034
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 2.1°
CCD_Profile_fitting scans	h = −20→20
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −14→14
Tmin = 0.575, Tmax = 0.731	l = −16→16
24048 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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0591P)2 + 1.2714P] where P = (Fo2 + 2Fc2)/3
2755 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.81 e Å−3
0 restraints	Δρmin = −0.65 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
I1	1.020717 (13)	0.7500	0.497027 (14)	0.01781 (10)
N2	0.69020 (16)	0.7500	0.21864 (19)	0.0118 (5)
H2A	0.6919	0.6850	0.1782	0.018*
H2C	0.6440	0.7500	0.2599	0.018*
C25	0.87428 (14)	0.6439 (2)	0.37576 (16)	0.0155 (4)
H25A	0.8994	0.5711	0.3975	0.019*
C26	0.80150 (13)	0.64394 (18)	0.31502 (16)	0.0141 (4)
H26A	0.7757	0.5713	0.2941	0.017*
C27	0.76611 (18)	0.7500	0.2846 (2)	0.0116 (5)
C30	0.91063 (18)	0.7500	0.4050 (2)	0.0146 (6)
O4	0.79657 (9)	0.45595 (13)	0.59043 (12)	0.0152 (3)
O5	0.70915 (15)	0.2500	0.52965 (18)	0.0158 (4)
C6	0.81605 (14)	0.56511 (19)	0.64275 (17)	0.0160 (4)
H6A	0.7730	0.5830	0.6947	0.019*
H6B	0.8177	0.6286	0.5917	0.019*
C7	0.71692 (14)	0.4594 (2)	0.53731 (19)	0.0176 (5)
H7A	0.7124	0.5309	0.4961	0.021*
H7B	0.6715	0.4584	0.5885	0.021*
C8	0.71071 (15)	0.3540 (2)	0.46600 (18)	0.0182 (5)
H8A	0.6598	0.3587	0.4239	0.022*
H8B	0.7586	0.3518	0.4186	0.022*
O1	0.89363 (9)	0.46966 (13)	0.78008 (12)	0.0141 (3)
O2	0.95815 (15)	0.2500	0.84574 (18)	0.0137 (4)
C1	0.97204 (13)	0.4574 (2)	0.83409 (18)	0.0155 (4)
H1A	0.9841	0.5282	0.8739	0.019*
H1B	1.0171	0.4456	0.7835	0.019*
C2	0.96711 (14)	0.35433 (19)	0.90738 (17)	0.0150 (4)
H2D	1.0178	0.3498	0.9499	0.018*
H2E	0.9193	0.3629	0.9543	0.018*
Cl1	0.60734 (4)	0.7500	0.70231 (5)	0.01306 (16)
O17	0.62206 (10)	0.64643 (15)	0.76547 (13)	0.0230 (4)
O21	0.52124 (13)	0.7500	0.6644 (2)	0.0173 (5)
O22	0.66395 (14)	0.7500	0.61313 (17)	0.0179 (5)
C5	0.90019 (14)	0.55317 (19)	0.69569 (17)	0.0157 (4)
H5A	0.9419	0.5269	0.6450	0.019*
H5B	0.9179	0.6287	0.7233	0.019*

	U11	U22	U33	U12	U13	U23
I1	0.01152 (15)	0.02558 (16)	0.01632 (15)	0.000	−0.00231 (6)	0.000
N2	0.0115 (11)	0.0107 (11)	0.0132 (11)	0.000	0.0000 (10)	0.000
C25	0.0162 (10)	0.0170 (10)	0.0135 (9)	0.0027 (8)	0.0001 (8)	0.0020 (8)
C26	0.0154 (10)	0.0123 (10)	0.0145 (10)	−0.0008 (8)	0.0009 (8)	−0.0015 (8)
C27	0.0095 (13)	0.0148 (14)	0.0104 (13)	0.000	0.0009 (11)	0.000
C30	0.0101 (13)	0.0228 (15)	0.0108 (13)	0.000	0.0019 (11)	0.000
O4	0.0136 (7)	0.0131 (7)	0.0189 (7)	0.0020 (6)	−0.0022 (6)	0.0007 (6)
O5	0.0195 (11)	0.0148 (11)	0.0131 (10)	0.000	−0.0012 (9)	0.000
C6	0.0195 (10)	0.0107 (10)	0.0177 (10)	0.0017 (8)	0.0015 (9)	0.0025 (8)
C7	0.0152 (10)	0.0195 (11)	0.0180 (11)	0.0027 (8)	−0.0034 (9)	0.0037 (9)
C8	0.0181 (11)	0.0235 (12)	0.0128 (10)	0.0002 (9)	−0.0026 (9)	0.0047 (9)
O1	0.0130 (7)	0.0137 (7)	0.0156 (7)	−0.0019 (5)	−0.0003 (6)	0.0031 (6)
O2	0.0184 (10)	0.0099 (10)	0.0128 (10)	0.000	−0.0013 (9)	0.000
C1	0.0137 (10)	0.0138 (11)	0.0189 (11)	−0.0020 (8)	−0.0009 (8)	−0.0013 (8)
C2	0.0158 (10)	0.0142 (10)	0.0151 (10)	0.0002 (8)	−0.0015 (8)	−0.0027 (8)
Cl1	0.0118 (3)	0.0126 (3)	0.0148 (3)	0.000	0.0005 (3)	0.000
O17	0.0210 (8)	0.0224 (9)	0.0257 (9)	0.0028 (7)	0.0004 (7)	0.0111 (7)
O21	0.0116 (11)	0.0177 (12)	0.0225 (13)	0.000	−0.0016 (8)	0.000
O22	0.0154 (11)	0.0215 (11)	0.0169 (11)	0.000	0.0053 (9)	0.000
C5	0.0188 (10)	0.0120 (10)	0.0163 (10)	−0.0030 (8)	0.0027 (8)	0.0021 (8)

I1—C30	2.102 (3)	C7—H7A	0.9700
N2—C27	1.467 (4)	C7—H7B	0.9702
N2—H2A	0.9002	C8—H8A	0.9700
N2—H2C	0.9006	C8—H8B	0.9700
C25—C26	1.389 (3)	O1—C1	1.428 (3)
C25—C30	1.390 (3)	O1—C5	1.435 (2)
C25—H25A	0.9599	O2—C2	1.429 (2)
C26—C27	1.387 (3)	O2—C2ii	1.429 (2)
C26—H26A	0.9601	C1—C2	1.499 (3)
C27—C26i	1.387 (3)	C1—H1A	0.9699
C30—C25i	1.390 (3)	C1—H1B	0.9700
O4—C7	1.433 (3)	C2—H2D	0.9701
O4—C6	1.443 (3)	C2—H2E	0.9701
O5—C8ii	1.433 (3)	Cl1—O22	1.444 (2)
O5—C8	1.433 (3)	Cl1—O17i	1.4445 (16)
C6—C5	1.501 (3)	Cl1—O17	1.4445 (16)
C6—H6A	0.9700	Cl1—O21	1.449 (2)
C6—H6B	0.9701	C5—H5A	0.9701
C7—C8	1.506 (3)	C5—H5B	0.9700
C27—N2—H2A	107.4	C7—C8—H8A	110.0
C27—N2—H2C	109.7	O5—C8—H8B	109.9
H2A—N2—H2C	110.8	C7—C8—H8B	109.9
C26—C25—C30	119.5 (2)	H8A—C8—H8B	108.3
C26—C25—H25A	120.4	C1—O1—C5	111.03 (16)
C30—C25—H25A	120.1	C2—O2—C2ii	112.5 (2)
C27—C26—C25	119.5 (2)	O1—C1—C2	109.15 (17)
C27—C26—H26A	120.0	O1—C1—H1A	109.9
C25—C26—H26A	120.5	C2—C1—H1A	109.8
C26i—C27—C26	121.1 (3)	O1—C1—H1B	109.9
C26i—C27—N2	119.44 (13)	C2—C1—H1B	109.8
C26—C27—N2	119.44 (14)	H1A—C1—H1B	108.3
C25—C30—C25i	120.9 (3)	O2—C2—C1	108.51 (18)
C25—C30—I1	119.56 (14)	O2—C2—H2D	110.0
C25i—C30—I1	119.56 (14)	C1—C2—H2D	110.0
C7—O4—C6	112.42 (16)	O2—C2—H2E	110.0
C8ii—O5—C8	111.4 (2)	C1—C2—H2E	110.0
O4—C6—C5	108.56 (17)	H2D—C2—H2E	108.4
O4—C6—H6A	110.0	O22—Cl1—O17i	109.46 (9)
C5—C6—H6A	110.0	O22—Cl1—O17	109.46 (9)
O4—C6—H6B	110.0	O17i—Cl1—O17	109.47 (15)
C5—C6—H6B	110.0	O22—Cl1—O21	109.14 (14)
H6A—C6—H6B	108.4	O17i—Cl1—O21	109.65 (9)
O4—C7—C8	108.52 (18)	O17—Cl1—O21	109.65 (9)
O4—C7—H7A	110.0	O1—C5—C6	109.19 (17)
C8—C7—H7A	109.9	O1—C5—H5A	109.8
O4—C7—H7B	110.0	C6—C5—H5A	109.9
C8—C7—H7B	110.0	O1—C5—H5B	109.9
H7A—C7—H7B	108.4	C6—C5—H5B	109.8
O5—C8—C7	108.78 (18)	H5A—C5—H5B	108.3
O5—C8—H8A	109.9

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O4iii	0.90	1.96	2.861 (2)	176
N2—H2C···O2iii	0.90	1.95	2.854 (3)	178

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O4i	0.90	1.96	2.861 (2)	176
N2—H2C⋯O2i	0.90	1.95	2.854 (3)	178

Symmetry code: (i) .