Benzyl­aminium perchlorate–18-crown-6 (1/1)

Wang, W.; Li, X.; Wang, N.

doi:10.1107/S1600536811007082

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o772

doi:10.1107/S1600536811007082

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Benzylaminium perchlorate–18-crown-6 (1/1)

Wen-zhe Wang,^a ^* Xiu-juan Li ^a and Na Wang ^a

^aRiZhao Polytechnic, RiZhao 276826, People's Republic of China
^*Correspondence e-mail: wangwenzhe-11@163.com

(Received 21 January 2011; accepted 24 February 2011; online 2 March 2011)

In the title compound, C₇H₁₀N⁺·ClO₄⁻·C₂₀H₂₄O₆, the protonated benzylamine cation forms a rotator–stator complex with the 18-crown-6 (1,4,7,10,13,16-hexaoxacyclooctadecane) molecule via N—H⋯O hydrogen bonds. The cations are associated via weak C—H⋯π interactions, forming chains parallel to [011], while the perclorate anions are located between these chains.

Related literature

For a related structure, see: Ge et al.. (2010 ).

Experimental

Crystal data

C₇H₁₀N⁺·ClO₄⁻·C₁₂H₂₄O₆
M_r = 471.92
Triclinic, $[P \overline 1]$
a = 9.3482 (19) Å
b = 10.948 (2) Å
c = 12.071 (2) Å
α = 76.71 (3)°
β = 86.64 (3)°
γ = 78.27 (3)°
V = 1177.1 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 298 K
0.40 × 0.30 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.926, T_max = 0.958
12262 measured reflections
5391 independent reflections
3637 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.157
S = 1.03
5391 reflections
292 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C14–C19 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4	0.86 (2)	2.18 (2)	3.004 (3)	161 (3)
N1—H2⋯O2	0.84 (2)	2.11 (2)	2.938 (3)	174 (3)
N1—H3⋯O1	0.85 (2)	2.47 (2)	2.955 (3)	117 (2)
N1—H3⋯O6	0.85 (2)	2.07 (2)	2.885 (3)	162 (3)
C13—H13B⋯Cg1ⁱ	0.97	2.99	3.545 (3)	117
Symmetry code: (i) -x+1, -y+1, -z.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811007082/kp2306sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811007082/kp2306Isup2.hkl

checkCIF report

Comment top

The asymmetric unit of the title compound, (I), contains a 1:1 (C₇H₁₀N⁺)(18-crown-6) adduct forming the supramolecular cation and a perchlorate anion (Fig. 1). The 18-crown-6 molecule possesses a boat conformation, while the ammonium atom is in a forward perching position. The supramolecular cation is involved in three bifurcated hydrogen bonds, each to two adjacent oxygen atoms of the crown ring, with the hydrogen bond length from 2.885 (3) Å- 3.004 (3)Å (Table 1).

The pairwise face-to-face supramolecular cations are linked by C—H···Cgⁱ [symmetry code: (i) -x + 1, -y + 1, -z] interactions with C···centroid distances of 3.545 (3) Å, forming one-dimensional chains parallel to [0 1 1] (Fig. 2). The perchlorate anions are located between the chains of cations.

Related literature top

For related literature, see: Ge et al. (2010).

Experimental top

Benzylamine (1.07 g, 10 mmol) was firstly dissolved in methanol (20 mL), to which perchloraic acid aqueous solution was dropped slowly with stirring until pH of the solution gradually changed to ca 7.18-crown-6 (2.64 g 10 mmol) methanol solution was mixed. Methanol was added until the precipitated substrate disappeared, then the solution was allowed to slowly evaporate at room temperature until prisms of the title compound were grown.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. N-bound H atoms are shown as small spheres of arbitrary radii, all other H atoms have been omitted for clarity. Dashed lines indicate N—H···O hydrogen bonds.
	Fig. 2. A view of crystal packing with stacking parallel to [0 1 1]. Dashed lines indicate hydrogen bonds and C—H···π interactions. Cg denotes the ring centroid. [symmetry code: (i) -x + 1, -y + 1, -z]

Benzylaminium perchlorate–1,4,7,10,13,16-hexaoxacyclooctadecane (1/1) top

Crystal data top

C₇H₁₀N⁺·ClO₄⁻·C₁₂H₂₄O₆	Z = 2
M_r = 471.92	F(000) = 504
Triclinic, P1	D_x = 1.332 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3482 (19) Å	Cell parameters from 5069.5 reflections
b = 10.948 (2) Å	θ = 3.2–27.6°
c = 12.071 (2) Å	µ = 0.21 mm⁻¹
α = 76.71 (3)°	T = 298 K
β = 86.64 (3)°	Prism, colourless
γ = 78.27 (3)°	0.40 × 0.30 × 0.20 mm
V = 1177.1 (4) Å³

Data collection top

Rigaku SCXmini diffractometer	5391 independent reflections
Radiation source: fine-focus sealed tube	3637 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.2°
ω scans	h = −12→12
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −14→14
T_min = 0.926, T_max = 0.958	l = −15→15
12262 measured reflections

Refinement top

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.157	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0636P)² + 0.4966P] where P = (F_o² + 2F_c²)/3
5391 reflections	(Δ/σ)_max < 0.001
292 parameters	Δρ_max = 0.49 e Å⁻³
3 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₇H₁₀N⁺·ClO₄⁻·C₁₂H₂₄O₆	γ = 78.27 (3)°
M_r = 471.92	V = 1177.1 (4) Å³
Triclinic, P1	Z = 2
a = 9.3482 (19) Å	Mo Kα radiation
b = 10.948 (2) Å	µ = 0.21 mm⁻¹
c = 12.071 (2) Å	T = 298 K
α = 76.71 (3)°	0.40 × 0.30 × 0.20 mm
β = 86.64 (3)°

Data collection top

Rigaku SCXmini diffractometer	5391 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	3637 reflections with I > 2σ(I)
T_min = 0.926, T_max = 0.958	R_int = 0.036
12262 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	3 restraints
wR(F²) = 0.157	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.49 e Å⁻³
5391 reflections	Δρ_min = −0.32 e Å⁻³
292 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.09437 (7)	0.73666 (6)	0.23044 (6)	0.0524 (2)
N1	0.4131 (2)	0.2586 (2)	0.25044 (18)	0.0396 (4)
H3	0.328 (2)	0.241 (2)	0.262 (2)	0.055 (8)*
H2	0.434 (3)	0.280 (3)	0.309 (2)	0.080 (11)*
H1	0.473 (3)	0.191 (2)	0.242 (2)	0.061 (8)*
C1	0.0242 (3)	0.2263 (3)	0.3324 (2)	0.0539 (6)
H1A	0.0421	0.1450	0.3874	0.065*
H1B	−0.0765	0.2435	0.3083	0.065*
C2	0.0486 (3)	0.3295 (3)	0.3861 (2)	0.0570 (7)
H2A	0.0375	0.4099	0.3300	0.068*
H2B	−0.0228	0.3398	0.4465	0.068*
C3	0.2209 (3)	0.3866 (3)	0.4913 (2)	0.0574 (7)
H3A	0.1504	0.3930	0.5530	0.069*
H3B	0.2119	0.4703	0.4403	0.069*
C4	0.3716 (3)	0.3441 (3)	0.5380 (2)	0.0563 (7)
H4A	0.3864	0.3972	0.5889	0.068*
H4B	0.3844	0.2562	0.5811	0.068*
C5	0.6237 (3)	0.3138 (3)	0.4840 (3)	0.0619 (7)
H5A	0.6322	0.3391	0.5549	0.074*
H5B	0.6854	0.3574	0.4276	0.074*
C6	0.6772 (3)	0.1724 (3)	0.5013 (2)	0.0618 (7)
H6A	0.7751	0.1489	0.5319	0.074*
H6B	0.6138	0.1273	0.5549	0.074*
C7	0.7380 (3)	0.0069 (3)	0.4014 (3)	0.0622 (8)
H7A	0.6859	−0.0457	0.4588	0.075*
H7B	0.8397	−0.0112	0.4232	0.075*
C8	0.7269 (3)	−0.0241 (3)	0.2899 (3)	0.0605 (7)
H8A	0.7716	0.0334	0.2311	0.073*
H8B	0.7778	−0.1111	0.2916	0.073*
C9	0.5564 (3)	−0.0628 (3)	0.1715 (2)	0.0621 (7)
H9A	0.5974	−0.1538	0.1880	0.075*
H9B	0.6062	−0.0219	0.1048	0.075*
C10	0.3972 (3)	−0.0412 (3)	0.1491 (2)	0.0585 (7)
H10A	0.3805	−0.0887	0.0941	0.070*
H10B	0.3450	−0.0702	0.2189	0.070*
C11	0.1953 (3)	0.1244 (3)	0.0785 (2)	0.0574 (7)
H11A	0.1734	0.0645	0.0370	0.069*
H11B	0.1754	0.2091	0.0287	0.069*
C12	0.0963 (3)	0.1234 (3)	0.1806 (2)	0.0574 (7)
H12A	−0.0047	0.1405	0.1574	0.069*
H12B	0.1167	0.0400	0.2323	0.069*
C13	0.4150 (3)	0.3677 (3)	0.1516 (2)	0.0558 (7)
H13A	0.3409	0.4401	0.1630	0.067*
H13B	0.3909	0.3441	0.0833	0.067*
C14	0.5614 (2)	0.4067 (2)	0.13535 (19)	0.0410 (5)
C15	0.6709 (3)	0.3499 (2)	0.0712 (2)	0.0534 (6)
H15A	0.6544	0.2862	0.0369	0.064*
C16	0.8057 (3)	0.3872 (3)	0.0573 (2)	0.0619 (7)
H16A	0.8787	0.3488	0.0135	0.074*
C17	0.8306 (3)	0.4798 (3)	0.1078 (2)	0.0595 (7)
H17A	0.9213	0.5035	0.0996	0.071*
C18	0.7231 (3)	0.5378 (3)	0.1702 (2)	0.0590 (7)
H18A	0.7402	0.6018	0.2038	0.071*
C19	0.5883 (3)	0.5018 (2)	0.1837 (2)	0.0503 (6)
H19A	0.5152	0.5424	0.2260	0.060*
O1	0.19248 (17)	0.29632 (15)	0.43136 (15)	0.0486 (4)
O2	0.47524 (19)	0.35379 (16)	0.44750 (14)	0.0512 (4)
O3	0.67755 (19)	0.13841 (15)	0.39507 (15)	0.0521 (4)
O4	0.57664 (17)	−0.01084 (16)	0.26576 (14)	0.0482 (4)
O5	0.34709 (18)	0.09153 (16)	0.10618 (14)	0.0493 (4)
O6	0.11943 (17)	0.21897 (16)	0.23658 (15)	0.0490 (4)
O7	0.0730 (3)	0.7953 (3)	0.3246 (2)	0.1013 (8)
O8	0.0789 (4)	0.8327 (2)	0.1295 (2)	0.1123 (10)
O9	−0.0107 (4)	0.6649 (4)	0.2327 (3)	0.1528 (15)
O10	0.2345 (3)	0.6655 (4)	0.2346 (3)	0.1501 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0508 (4)	0.0502 (4)	0.0589 (4)	−0.0132 (3)	−0.0051 (3)	−0.0139 (3)
N1	0.0340 (11)	0.0437 (11)	0.0426 (11)	−0.0117 (9)	0.0003 (9)	−0.0089 (9)
C1	0.0352 (12)	0.0615 (16)	0.0613 (16)	−0.0114 (11)	0.0027 (11)	−0.0054 (13)
C2	0.0385 (13)	0.0610 (16)	0.0668 (17)	0.0017 (12)	0.0068 (12)	−0.0165 (14)
C3	0.0624 (17)	0.0521 (15)	0.0619 (17)	−0.0090 (13)	0.0110 (13)	−0.0263 (13)
C4	0.0761 (19)	0.0547 (15)	0.0440 (14)	−0.0201 (14)	0.0026 (13)	−0.0176 (12)
C5	0.0598 (17)	0.0690 (18)	0.0655 (18)	−0.0257 (14)	−0.0162 (14)	−0.0173 (14)
C6	0.0586 (16)	0.0673 (18)	0.0581 (17)	−0.0166 (14)	−0.0223 (13)	−0.0017 (14)
C7	0.0482 (15)	0.0481 (15)	0.085 (2)	−0.0051 (12)	−0.0271 (14)	−0.0004 (14)
C8	0.0390 (14)	0.0507 (15)	0.088 (2)	0.0001 (11)	−0.0036 (13)	−0.0139 (14)
C9	0.0764 (19)	0.0549 (16)	0.0515 (16)	0.0071 (14)	0.0016 (14)	−0.0227 (13)
C10	0.0798 (19)	0.0498 (15)	0.0509 (15)	−0.0147 (13)	−0.0110 (13)	−0.0171 (12)
C11	0.0550 (16)	0.0655 (17)	0.0556 (16)	−0.0152 (13)	−0.0123 (13)	−0.0153 (13)
C12	0.0465 (14)	0.0617 (16)	0.0717 (18)	−0.0219 (12)	−0.0040 (13)	−0.0195 (14)
C13	0.0471 (14)	0.0520 (15)	0.0625 (17)	−0.0177 (12)	−0.0168 (12)	0.0101 (12)
C14	0.0422 (12)	0.0407 (12)	0.0368 (12)	−0.0106 (10)	−0.0073 (9)	0.0019 (10)
C15	0.0675 (17)	0.0455 (14)	0.0469 (14)	−0.0100 (12)	−0.0067 (12)	−0.0092 (11)
C16	0.0521 (16)	0.0711 (19)	0.0523 (16)	0.0009 (14)	0.0109 (12)	−0.0070 (14)
C17	0.0477 (15)	0.0762 (19)	0.0526 (16)	−0.0236 (14)	0.0010 (12)	−0.0006 (14)
C18	0.0638 (17)	0.0609 (17)	0.0587 (16)	−0.0287 (14)	−0.0003 (14)	−0.0118 (14)
C19	0.0492 (14)	0.0542 (15)	0.0483 (14)	−0.0125 (12)	0.0054 (11)	−0.0122 (12)
O1	0.0421 (9)	0.0446 (9)	0.0602 (11)	−0.0030 (7)	0.0027 (8)	−0.0194 (8)
O2	0.0553 (10)	0.0568 (10)	0.0448 (10)	−0.0166 (8)	−0.0035 (8)	−0.0122 (8)
O3	0.0542 (10)	0.0435 (9)	0.0558 (11)	−0.0100 (8)	−0.0175 (8)	−0.0010 (8)
O4	0.0393 (9)	0.0531 (10)	0.0522 (10)	−0.0018 (7)	−0.0003 (7)	−0.0184 (8)
O5	0.0518 (10)	0.0485 (10)	0.0507 (10)	−0.0130 (8)	−0.0025 (8)	−0.0138 (8)
O6	0.0388 (9)	0.0510 (10)	0.0611 (11)	−0.0157 (7)	0.0037 (8)	−0.0153 (8)
O7	0.0982 (18)	0.133 (2)	0.0844 (17)	−0.0079 (16)	−0.0136 (14)	−0.0580 (17)
O8	0.166 (3)	0.0825 (17)	0.0832 (18)	−0.0337 (18)	−0.0295 (18)	0.0073 (14)
O9	0.179 (3)	0.161 (3)	0.162 (3)	−0.130 (3)	−0.004 (3)	−0.040 (2)
O10	0.101 (2)	0.179 (3)	0.132 (3)	0.065 (2)	−0.0001 (19)	−0.040 (2)

Geometric parameters (Å, º) top

Cl1—O9	1.372 (3)	C7—H7B	0.9700
Cl1—O10	1.378 (3)	C8—O4	1.423 (3)
Cl1—O8	1.407 (3)	C8—H8A	0.9700
Cl1—O7	1.414 (2)	C8—H8B	0.9700
N1—C13	1.484 (3)	C9—O4	1.421 (3)
N1—H3	0.847 (17)	C9—C10	1.489 (4)
N1—H2	0.836 (18)	C9—H9A	0.9700
N1—H1	0.858 (17)	C9—H9B	0.9700
C1—O6	1.424 (3)	C10—O5	1.416 (3)
C1—C2	1.486 (4)	C10—H10A	0.9700
C1—H1A	0.9700	C10—H10B	0.9700
C1—H1B	0.9700	C11—O5	1.431 (3)
C2—O1	1.427 (3)	C11—C12	1.497 (4)
C2—H2A	0.9700	C11—H11A	0.9700
C2—H2B	0.9700	C11—H11B	0.9700
C3—O1	1.425 (3)	C12—O6	1.425 (3)
C3—C4	1.492 (4)	C12—H12A	0.9700
C3—H3A	0.9700	C12—H12B	0.9700
C3—H3B	0.9700	C13—C14	1.503 (3)
C4—O2	1.417 (3)	C13—H13A	0.9700
C4—H4A	0.9700	C13—H13B	0.9700
C4—H4B	0.9700	C14—C19	1.375 (3)
C5—O2	1.431 (3)	C14—C15	1.380 (4)
C5—C6	1.497 (4)	C15—C16	1.392 (4)
C5—H5A	0.9700	C15—H15A	0.9300
C5—H5B	0.9700	C16—C17	1.360 (4)
C6—O3	1.415 (3)	C16—H16A	0.9300
C6—H6A	0.9700	C17—C18	1.361 (4)
C6—H6B	0.9700	C17—H17A	0.9300
C7—O3	1.421 (3)	C18—C19	1.385 (4)
C7—C8	1.476 (4)	C18—H18A	0.9300
C7—H7A	0.9700	C19—H19A	0.9300

O9—Cl1—O10	113.1 (3)	O4—C8—H8B	110.0
O9—Cl1—O8	108.3 (2)	C7—C8—H8B	110.0
O10—Cl1—O8	108.9 (2)	H8A—C8—H8B	108.3
O9—Cl1—O7	109.3 (2)	O4—C9—C10	109.1 (2)
O10—Cl1—O7	108.27 (19)	O4—C9—H9A	109.9
O8—Cl1—O7	108.82 (18)	C10—C9—H9A	109.9
C13—N1—H3	111.3 (18)	O4—C9—H9B	109.9
C13—N1—H2	109 (2)	C10—C9—H9B	109.9
H3—N1—H2	106 (3)	H9A—C9—H9B	108.3
C13—N1—H1	112.5 (19)	O5—C10—C9	108.1 (2)
H3—N1—H1	108 (3)	O5—C10—H10A	110.1
H2—N1—H1	110 (3)	C9—C10—H10A	110.1
O6—C1—C2	110.2 (2)	O5—C10—H10B	110.1
O6—C1—H1A	109.6	C9—C10—H10B	110.1
C2—C1—H1A	109.6	H10A—C10—H10B	108.4
O6—C1—H1B	109.6	O5—C11—C12	113.4 (2)
C2—C1—H1B	109.6	O5—C11—H11A	108.9
H1A—C1—H1B	108.1	C12—C11—H11A	108.9
O1—C2—C1	109.0 (2)	O5—C11—H11B	108.9
O1—C2—H2A	109.9	C12—C11—H11B	108.9
C1—C2—H2A	109.9	H11A—C11—H11B	107.7
O1—C2—H2B	109.9	O6—C12—C11	109.1 (2)
C1—C2—H2B	109.9	O6—C12—H12A	109.9
H2A—C2—H2B	108.3	C11—C12—H12A	109.9
O1—C3—C4	109.2 (2)	O6—C12—H12B	109.9
O1—C3—H3A	109.8	C11—C12—H12B	109.9
C4—C3—H3A	109.8	H12A—C12—H12B	108.3
O1—C3—H3B	109.8	N1—C13—C14	111.97 (19)
C4—C3—H3B	109.8	N1—C13—H13A	109.2
H3A—C3—H3B	108.3	C14—C13—H13A	109.2
O2—C4—C3	109.6 (2)	N1—C13—H13B	109.2
O2—C4—H4A	109.7	C14—C13—H13B	109.2
C3—C4—H4A	109.7	H13A—C13—H13B	107.9
O2—C4—H4B	109.7	C19—C14—C15	118.4 (2)
C3—C4—H4B	109.7	C19—C14—C13	120.2 (2)
H4A—C4—H4B	108.2	C15—C14—C13	121.4 (2)
O2—C5—C6	112.9 (2)	C14—C15—C16	120.6 (2)
O2—C5—H5A	109.0	C14—C15—H15A	119.7
C6—C5—H5A	109.0	C16—C15—H15A	119.7
O2—C5—H5B	109.0	C17—C16—C15	119.9 (3)
C6—C5—H5B	109.0	C17—C16—H16A	120.0
H5A—C5—H5B	107.8	C15—C16—H16A	120.0
O3—C6—C5	108.5 (2)	C16—C17—C18	120.2 (3)
O3—C6—H6A	110.0	C16—C17—H17A	119.9
C5—C6—H6A	110.0	C18—C17—H17A	119.9
O3—C6—H6B	110.0	C17—C18—C19	120.1 (3)
C5—C6—H6B	110.0	C17—C18—H18A	119.9
H6A—C6—H6B	108.4	C19—C18—H18A	119.9
O3—C7—C8	109.8 (2)	C14—C19—C18	120.8 (2)
O3—C7—H7A	109.7	C14—C19—H19A	119.6
C8—C7—H7A	109.7	C18—C19—H19A	119.6
O3—C7—H7B	109.7	C3—O1—C2	112.38 (19)
C8—C7—H7B	109.7	C4—O2—C5	113.7 (2)
H7A—C7—H7B	108.2	C6—O3—C7	112.5 (2)
O4—C8—C7	108.7 (2)	C9—O4—C8	112.3 (2)
O4—C8—H8A	110.0	C10—O5—C11	113.4 (2)
C7—C8—H8A	110.0	C1—O6—C12	111.88 (18)

O6—C1—C2—O1	−65.1 (3)	C13—C14—C19—C18	179.5 (2)
O1—C3—C4—O2	68.5 (3)	C17—C18—C19—C14	0.5 (4)
O2—C5—C6—O3	64.3 (3)	C4—C3—O1—C2	178.8 (2)
O3—C7—C8—O4	−66.0 (3)	C1—C2—O1—C3	−176.0 (2)
O4—C9—C10—O5	69.6 (3)	C3—C4—O2—C5	−179.4 (2)
O5—C11—C12—O6	63.4 (3)	C6—C5—O2—C4	84.9 (3)
N1—C13—C14—C19	−93.2 (3)	C5—C6—O3—C7	175.3 (2)
N1—C13—C14—C15	87.6 (3)	C8—C7—O3—C6	176.5 (2)
C19—C14—C15—C16	0.8 (4)	C10—C9—O4—C8	−178.0 (2)
C13—C14—C15—C16	−179.9 (2)	C7—C8—O4—C9	−168.3 (2)
C14—C15—C16—C17	0.4 (4)	C9—C10—O5—C11	178.6 (2)
C15—C16—C17—C18	−1.2 (4)	C12—C11—O5—C10	76.3 (3)
C16—C17—C18—C19	0.8 (4)	C2—C1—O6—C12	−178.3 (2)
C15—C14—C19—C18	−1.3 (4)	C11—C12—O6—C1	177.8 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C14–C19 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H3···O1	0.85 (2)	2.47 (2)	2.955 (3)	117 (2)
N1—H2···O2	0.84 (2)	2.11 (2)	2.938 (3)	174 (3)
N1—H2···O3	0.84 (2)	2.60 (3)	3.003 (3)	111 (2)
N1—H1···O4	0.86 (2)	2.18 (2)	3.004 (3)	161 (3)
N1—H1···O5	0.86 (2)	2.61 (3)	2.968 (3)	107 (2)
N1—H3···O6	0.85 (2)	2.07 (2)	2.885 (3)	162 (3)
C13—H13B···Cg1ⁱ	0.97	2.99	3.545 (3)	117

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₇H₁₀N⁺·ClO₄⁻·C₁₂H₂₄O₆
M_r	471.92
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	9.3482 (19), 10.948 (2), 12.071 (2)
α, β, γ (°)	76.71 (3), 86.64 (3), 78.27 (3)
V (Å³)	1177.1 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.926, 0.958
No. of measured, independent and observed [I > 2σ(I)] reflections	12262, 5391, 3637
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.157, 1.03
No. of reflections	5391
No. of parameters	292
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.32

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C14–C19 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H3···O1	0.847 (17)	2.47 (2)	2.955 (3)	117 (2)
N1—H2···O2	0.836 (18)	2.105 (19)	2.938 (3)	174 (3)
N1—H2···O3	0.836 (18)	2.60 (3)	3.003 (3)	111 (2)
N1—H1···O4	0.858 (17)	2.182 (19)	3.004 (3)	161 (3)
N1—H1···O5	0.858 (17)	2.61 (3)	2.968 (3)	107 (2)
N1—H3···O6	0.847 (17)	2.067 (18)	2.885 (3)	162 (3)
C13—H13B···Cg1ⁱ	0.97	2.9934	3.545 (3)	117.32

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

The authors are grateful to RiZhao Polytechnic for support.

References

Ge, J.-Z., Fu, X.-Q., Hang, T., Ye, Q. & Xiong, R.-G. (2010). Cryst. Growth Des. 10, 3632–3637. CrossRef CAS Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 4| April 2011| Page o772

doi:10.1107/S1600536811007082

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