2,4,5-Trichloro­anilinium perchlorate 18-crown-6 clathrate

Xu, J.

doi:10.1107/S1600536812006162

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o739

doi:10.1107/S1600536812006162

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2,4,5-Trichloroanilinium perchlorate 18-crown-6 clathrate

Jie Xu ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: chemcrystal66@yahoo.com.cn

(Received 4 February 2012; accepted 12 February 2012; online 17 February 2012)

In the title compound, C₆H₅Cl₃N⁺·ClO₄⁻·C₁₂H₂₄O₆, the perchlorate anion is disordered over two orientations in a 0.666 (17):0.334 (17) ratio. The ammonium group of the organic cation inserts into the crown ether ring and forms three bifurcated N—H⋯(O,O) hydrogen bonds to generate a supramolecular complex. The macrocycle has approximate D_3d local symmetry.

Related literature

For background to molecular ferroelectric materials, see: Fu et al. (2011 ).

Experimental

Crystal data

C₆H₅Cl₃N⁺·ClO₄⁻·C₁₂H₂₄O₆
M_r = 561.22
Triclinic, $[P \overline 1]$
a = 9.4961 (19) Å
b = 11.783 (2) Å
c = 11.852 (2) Å
α = 97.86 (3)°
β = 90.39 (3)°
γ = 105.26 (3)°
V = 1266.1 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.52 mm⁻¹
T = 298 K
0.10 × 0.05 × 0.05 mm

Data collection

Rigaku Mercury2 (2 × 2 bin mode) diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.910, T_max = 1.000
11310 measured reflections
4713 independent reflections
3562 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.152
S = 1.03
4713 reflections
346 parameters
18 restraints
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯O1ⁱ	0.89	2.13	2.916 (3)	147
N1—H1C⋯O6ⁱ	0.89	2.21	2.899 (3)	134
N1—H1D⋯O5ⁱ	0.89	2.06	2.896 (3)	156
N1—H1D⋯O4ⁱ	0.89	2.52	3.052 (3)	119
N1—H1E⋯O3ⁱ	0.89	2.19	3.046 (3)	161
N1—H1E⋯O2ⁱ	0.89	2.35	2.856 (3)	116
Symmetry code: (i) -x+1, -y+1, -z+1.

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/S1600536812006162/hb6625sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812006162/hb6625Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812006162/hb6625Isup3.cml

checkCIF report

Comment top

With the purpose of obtaining phase transition crystals of amino compounds, various amines have been studied and we have elaborated a series of new materials with this organic molecules (Fu et al. 2011). In this study, we describe the crystal structure of the title compound, (I).

The title compound was composed of cationic [(C₆H₅NCl₃).(C₁₂H₂₄O₆)]⁺ and one ClO₄^- anion (Fig.1). Supramolecular cation was assembled by protonated 2,4,5-trichloroanilinium and 18-crown-6 through six strong N—H···O hydrogen bonds. The C-N bonds of cation were almost perpendicular to the mean oxygen planes of crown ethers. The macrocycle adopts a conformation with approximate D_3d symmetry, with all O-C-C-O torsion angles being gauche and alternating in sign, and all C-O-C-C torsion angles being anti. Supramolecular cation structure, [(C₆H₅NCl₃).(C₁₂H₂₄O₆)]⁺, was introduced as counter cation to ClO₄^- anion. Cl has a flattened tetrahedral coordination by four O atoms. The ClO₄^- anion is disordered over two sets of sites with refined occupancies 0.666 (17) and 0.334 (17).

The title compound was stabilized by intermolecular N—H···O hydrogen bonds, the ClO₄^- anion not participating in the H-bonding interactions. The intermolecular N—H···O H-bonding length are within the usual range of 2.856 (3) to 3.052 (3)Å. (Table 1 and Fig.2).

Related literature top

For background to molecular ferroelectric materials, see: Fu et al. (2011).

Experimental top

18-Crown-6 (6 mmol), HClO₄ (6 mmol) and 2,4,5-trichloroaniline (3 mmol) were dissolved in water/EtOH (1:1 v/v) solvent. The solution was slowly evaporated in air affording colourless blocks.

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. A view of the title compound with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The crystal packing of the title compound, showing the H-bonding interactions. H atoms not involved in hydrogen bonding (dashed line) have been omitted for clarity.

2,4,5-Trichloroanilinium perchlorate 1,4,7,10,13,16-hexaoxacyclooctadecane top

Crystal data top

C₆H₅Cl₃N⁺·ClO₄⁻·C₁₂H₂₄O₆	Z = 2
M_r = 561.22	F(000) = 584
Triclinic, P1	D_x = 1.472 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4961 (19) Å	Cell parameters from 4713 reflections
b = 11.783 (2) Å	θ = 3.1–26.5°
c = 11.852 (2) Å	µ = 0.52 mm⁻¹
α = 97.86 (3)°	T = 298 K
β = 90.39 (3)°	Block, colourless
γ = 105.26 (3)°	0.10 × 0.05 × 0.05 mm
V = 1266.1 (4) Å³

Data collection top

Rigaku Mercury2 (2x2 bin mode) diffractometer	4713 independent reflections
Radiation source: fine-focus sealed tube	3562 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
Detector resolution: 13.6612 pixels mm^-1	θ_max = 25.5°, θ_min = 3.1°
CCD profile fitting scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −14→14
T_min = 0.910, T_max = 1.000	l = −14→14
11310 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.054	H-atom parameters constrained
wR(F²) = 0.152	w = 1/[σ²(F_o²) + (0.070P)² + 0.575P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
4713 reflections	Δρ_max = 0.57 e Å⁻³
346 parameters	Δρ_min = −0.28 e Å⁻³
18 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.019 (2)

Crystal data top

C₆H₅Cl₃N⁺·ClO₄⁻·C₁₂H₂₄O₆	γ = 105.26 (3)°
M_r = 561.22	V = 1266.1 (4) Å³
Triclinic, P1	Z = 2
a = 9.4961 (19) Å	Mo Kα radiation
b = 11.783 (2) Å	µ = 0.52 mm⁻¹
c = 11.852 (2) Å	T = 298 K
α = 97.86 (3)°	0.10 × 0.05 × 0.05 mm
β = 90.39 (3)°

Data collection top

Rigaku Mercury2 (2x2 bin mode) diffractometer	4713 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	3562 reflections with I > 2σ(I)
T_min = 0.910, T_max = 1.000	R_int = 0.042
11310 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	18 restraints
wR(F²) = 0.152	H-atom parameters constrained
S = 1.03	Δρ_max = 0.57 e Å⁻³
4713 reflections	Δρ_min = −0.28 e Å⁻³
346 parameters

Special details top

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 > 2sigma(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	Occ. (<1)
Cl1	0.30933 (8)	0.67394 (7)	0.38541 (7)	0.0584 (3)
N1	0.5852 (2)	0.7317 (2)	0.25875 (17)	0.0421 (5)
H1C	0.6761	0.7384	0.2370	0.063*
H1D	0.5358	0.7570	0.2078	0.063*
H1E	0.5417	0.6559	0.2637	0.063*
Cl2	0.60060 (12)	1.00366 (8)	0.72283 (6)	0.0763 (3)
C18	0.5882 (3)	0.8037 (2)	0.3703 (2)	0.0366 (6)
Cl3	0.86985 (10)	1.06897 (8)	0.56512 (8)	0.0800 (3)
C13	0.4666 (3)	0.7804 (2)	0.4375 (2)	0.0408 (6)
C15	0.5973 (4)	0.9285 (3)	0.5859 (2)	0.0492 (7)
C16	0.7156 (3)	0.9555 (3)	0.5175 (2)	0.0489 (7)
O3	0.5578 (2)	0.53489 (19)	0.78658 (19)	0.0616 (6)
O1	0.1138 (2)	0.2827 (2)	0.7236 (2)	0.0636 (6)
C17	0.7111 (3)	0.8924 (2)	0.4094 (2)	0.0458 (6)
H17A	0.7908	0.9100	0.3635	0.055*
C14	0.4716 (3)	0.8432 (2)	0.5456 (2)	0.0467 (7)
H14A	0.3908	0.8279	0.5906	0.056*
O2	0.3401 (3)	0.43429 (19)	0.61331 (18)	0.0643 (6)
O4	0.6757 (3)	0.3898 (2)	0.90636 (19)	0.0747 (7)
O6	0.2005 (3)	0.1902 (2)	0.9069 (2)	0.0697 (6)
O5	0.4919 (3)	0.1617 (2)	0.93064 (19)	0.0773 (7)
C1	0.0241 (4)	0.2633 (4)	0.8172 (3)	0.0762 (11)
H1A	−0.0777	0.2451	0.7919	0.091*
H1B	0.0459	0.3346	0.8730	0.091*
C9	0.5364 (5)	0.5924 (3)	0.6920 (3)	0.0813 (12)
H9A	0.5927	0.5699	0.6289	0.098*
H9B	0.5691	0.6780	0.7131	0.098*
C10	0.3801 (5)	0.5564 (3)	0.6579 (3)	0.0776 (11)
H10A	0.3230	0.5705	0.7234	0.093*
H10B	0.3611	0.6027	0.6007	0.093*
C6	0.6873 (5)	0.3373 (4)	1.0053 (3)	0.0837 (12)
H6A	0.6265	0.3631	1.0634	0.100*
H6B	0.7877	0.3616	1.0352	0.100*
C8	0.7075 (4)	0.5679 (3)	0.8253 (4)	0.0799 (11)
H8A	0.7437	0.6538	0.8398	0.096*
H8B	0.7656	0.5379	0.7674	0.096*
C7	0.7188 (4)	0.5178 (4)	0.9294 (4)	0.0877 (13)
H7A	0.8187	0.5450	0.9605	0.105*
H7B	0.6565	0.5448	0.9856	0.105*
C2	0.0499 (4)	0.1641 (4)	0.8693 (3)	0.0841 (13)
H2A	−0.0118	0.1507	0.9337	0.101*
H2B	0.0249	0.0922	0.8142	0.101*
C3	0.2348 (6)	0.1026 (4)	0.9654 (4)	0.0952 (14)
H3A	0.2244	0.0297	0.9131	0.114*
H3B	0.1678	0.0855	1.0261	0.114*
C11	0.1938 (5)	0.3922 (4)	0.5702 (4)	0.0843 (12)
H11A	0.1828	0.3183	0.5193	0.101*
H11B	0.1721	0.4495	0.5261	0.101*
C12	0.0878 (4)	0.3719 (4)	0.6604 (4)	0.0899 (13)
H12A	0.0972	0.4455	0.7115	0.108*
H12B	−0.0107	0.3460	0.6265	0.108*
C5	0.6391 (5)	0.2059 (4)	0.9751 (3)	0.0909 (13)
H5A	0.7031	0.1814	0.9190	0.109*
H5B	0.6493	0.1700	1.0426	0.109*
C4	0.3898 (7)	0.1477 (5)	1.0147 (4)	0.1070 (17)
H4A	0.4008	0.2236	1.0625	0.128*
H4B	0.4087	0.0923	1.0625	0.128*
Cl4	0.0719 (14)	0.7626 (15)	0.7497 (13)	0.128 (4)	0.334 (17)
O10	0.040 (2)	0.7880 (19)	0.8570 (11)	0.121 (7)	0.334 (17)
O9	0.053 (3)	0.653 (2)	0.703 (3)	0.152 (7)	0.334 (17)
O8	0.2286 (19)	0.797 (2)	0.7517 (18)	0.116 (6)	0.334 (17)
O7	−0.056 (2)	0.790 (2)	0.6899 (19)	0.143 (7)	0.334 (17)
Cl4'	0.0736 (4)	0.7704 (3)	0.7438 (2)	0.0580 (11)	0.666 (17)
O10'	0.0532 (11)	0.7151 (19)	0.8447 (12)	0.190 (7)	0.666 (17)
O8'	−0.0154 (17)	0.8368 (11)	0.7385 (16)	0.194 (6)	0.666 (17)
O7'	0.0428 (16)	0.6824 (13)	0.6488 (9)	0.170 (5)	0.666 (17)
O9'	0.2038 (16)	0.8551 (14)	0.7353 (12)	0.192 (7)	0.666 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0438 (4)	0.0646 (5)	0.0609 (5)	0.0076 (3)	0.0091 (3)	0.0018 (4)
N1	0.0388 (11)	0.0521 (13)	0.0324 (11)	0.0092 (10)	0.0006 (9)	0.0014 (9)
Cl2	0.1349 (9)	0.0625 (5)	0.0344 (4)	0.0375 (5)	0.0029 (4)	−0.0051 (3)
C18	0.0411 (14)	0.0425 (14)	0.0288 (12)	0.0160 (11)	0.0007 (10)	0.0040 (10)
Cl3	0.0662 (6)	0.0702 (6)	0.0860 (7)	0.0096 (4)	−0.0143 (5)	−0.0312 (5)
C13	0.0474 (15)	0.0392 (14)	0.0388 (14)	0.0152 (12)	0.0034 (11)	0.0084 (11)
C15	0.080 (2)	0.0444 (16)	0.0293 (13)	0.0286 (15)	−0.0014 (13)	0.0032 (11)
C16	0.0540 (17)	0.0456 (16)	0.0457 (16)	0.0170 (13)	−0.0099 (13)	−0.0055 (12)
O3	0.0480 (12)	0.0607 (13)	0.0674 (14)	0.0004 (10)	0.0010 (10)	0.0068 (11)
O1	0.0443 (12)	0.0651 (14)	0.0767 (15)	0.0104 (10)	0.0073 (11)	0.0020 (11)
C17	0.0441 (15)	0.0490 (16)	0.0422 (15)	0.0127 (12)	0.0014 (12)	−0.0010 (12)
C14	0.0670 (18)	0.0451 (16)	0.0352 (14)	0.0247 (14)	0.0150 (13)	0.0108 (12)
O2	0.0764 (15)	0.0543 (13)	0.0599 (13)	0.0113 (11)	−0.0039 (11)	0.0126 (10)
O4	0.0741 (16)	0.0865 (18)	0.0550 (14)	0.0184 (13)	−0.0222 (12)	−0.0125 (12)
O6	0.0624 (14)	0.0651 (15)	0.0746 (15)	0.0004 (11)	0.0200 (12)	0.0182 (12)
O5	0.103 (2)	0.0890 (18)	0.0466 (13)	0.0389 (15)	−0.0023 (13)	0.0064 (12)
C1	0.0423 (18)	0.092 (3)	0.079 (2)	0.0084 (18)	0.0038 (17)	−0.022 (2)
C9	0.113 (3)	0.052 (2)	0.065 (2)	−0.005 (2)	0.015 (2)	0.0152 (17)
C10	0.121 (3)	0.051 (2)	0.060 (2)	0.021 (2)	−0.015 (2)	0.0118 (16)
C6	0.088 (3)	0.106 (3)	0.056 (2)	0.042 (2)	−0.0287 (19)	−0.019 (2)
C8	0.056 (2)	0.065 (2)	0.097 (3)	−0.0067 (17)	−0.0035 (19)	−0.020 (2)
C7	0.071 (2)	0.089 (3)	0.081 (3)	0.006 (2)	−0.030 (2)	−0.033 (2)
C2	0.064 (2)	0.094 (3)	0.065 (2)	−0.024 (2)	0.0227 (18)	−0.004 (2)
C3	0.130 (4)	0.076 (3)	0.076 (3)	0.011 (3)	0.031 (3)	0.031 (2)
C11	0.088 (3)	0.081 (3)	0.086 (3)	0.018 (2)	−0.025 (2)	0.027 (2)
C12	0.058 (2)	0.076 (3)	0.139 (4)	0.023 (2)	−0.024 (2)	0.020 (3)
C5	0.111 (3)	0.103 (3)	0.067 (2)	0.054 (3)	−0.031 (2)	−0.008 (2)
C4	0.151 (5)	0.135 (4)	0.061 (3)	0.072 (4)	0.016 (3)	0.035 (3)
Cl4	0.090 (6)	0.144 (8)	0.143 (8)	0.028 (6)	−0.025 (6)	0.004 (7)
O10	0.135 (11)	0.177 (15)	0.031 (6)	0.018 (10)	0.037 (6)	−0.010 (8)
O9	0.148 (11)	0.102 (10)	0.203 (17)	0.057 (9)	−0.002 (13)	−0.030 (12)
O8	0.058 (6)	0.188 (15)	0.089 (7)	0.017 (9)	0.016 (5)	0.010 (10)
O7	0.117 (9)	0.173 (15)	0.138 (11)	0.020 (10)	−0.047 (9)	0.060 (10)
Cl4'	0.0618 (17)	0.0635 (16)	0.0419 (15)	0.0072 (12)	0.0088 (11)	0.0024 (10)
O10'	0.089 (5)	0.337 (18)	0.144 (9)	−0.002 (8)	−0.019 (5)	0.153 (11)
O8'	0.194 (12)	0.141 (8)	0.264 (15)	0.093 (8)	−0.029 (10)	−0.008 (8)
O7'	0.235 (10)	0.144 (9)	0.114 (6)	0.056 (7)	−0.074 (6)	−0.049 (6)
O9'	0.149 (10)	0.187 (11)	0.152 (9)	−0.087 (8)	0.067 (8)	−0.022 (8)

Geometric parameters (Å, º) top

Cl1—C13	1.724 (3)	C10—H10A	0.9700
N1—C18	1.466 (3)	C10—H10B	0.9700
N1—H1C	0.8900	C6—C5	1.486 (6)
N1—H1D	0.8900	C6—H6A	0.9700
N1—H1E	0.8900	C6—H6B	0.9700
Cl2—C15	1.735 (3)	C8—C7	1.454 (6)
C18—C17	1.374 (4)	C8—H8A	0.9700
C18—C13	1.395 (4)	C8—H8B	0.9700
Cl3—C16	1.733 (3)	C7—H7A	0.9700
C13—C14	1.383 (4)	C7—H7B	0.9700
C15—C14	1.376 (4)	C2—H2A	0.9700
C15—C16	1.383 (4)	C2—H2B	0.9700
C16—C17	1.385 (4)	C3—C4	1.511 (7)
O3—C8	1.425 (4)	C3—H3A	0.9700
O3—C9	1.427 (4)	C3—H3B	0.9700
O1—C1	1.409 (4)	C11—C12	1.473 (6)
O1—C12	1.441 (4)	C11—H11A	0.9700
C17—H17A	0.9300	C11—H11B	0.9700
C14—H14A	0.9300	C12—H12A	0.9700
O2—C11	1.412 (4)	C12—H12B	0.9700
O2—C10	1.413 (4)	C5—H5A	0.9700
O4—C6	1.415 (5)	C5—H5B	0.9700
O4—C7	1.442 (5)	C4—H4A	0.9700
O6—C3	1.422 (5)	C4—H4B	0.9700
O6—C2	1.436 (4)	Cl4—O9	1.30 (2)
O5—C4	1.391 (5)	Cl4—O10	1.322 (19)
O5—C5	1.426 (5)	Cl4—O8	1.43 (2)
C1—C2	1.468 (6)	Cl4—O7	1.53 (2)
C1—H1A	0.9700	Cl4'—O8'	1.300 (13)
C1—H1B	0.9700	Cl4'—O9'	1.384 (11)
C9—C10	1.470 (6)	Cl4'—O7'	1.395 (10)
C9—H9A	0.9700	Cl4'—O10'	1.428 (12)
C9—H9B	0.9700

C18—N1—H1C	109.5	O3—C8—H8B	110.0
C18—N1—H1D	109.5	C7—C8—H8B	110.0
H1C—N1—H1D	109.5	H8A—C8—H8B	108.4
C18—N1—H1E	109.5	O4—C7—C8	110.2 (3)
H1C—N1—H1E	109.5	O4—C7—H7A	109.6
H1D—N1—H1E	109.5	C8—C7—H7A	109.6
C17—C18—C13	120.2 (2)	O4—C7—H7B	109.6
C17—C18—N1	120.1 (2)	C8—C7—H7B	109.6
C13—C18—N1	119.7 (2)	H7A—C7—H7B	108.1
C14—C13—C18	120.1 (3)	O6—C2—C1	110.1 (3)
C14—C13—Cl1	119.9 (2)	O6—C2—H2A	109.6
C18—C13—Cl1	120.1 (2)	C1—C2—H2A	109.6
C14—C15—C16	120.6 (2)	O6—C2—H2B	109.6
C14—C15—Cl2	118.0 (2)	C1—C2—H2B	109.6
C16—C15—Cl2	121.3 (2)	H2A—C2—H2B	108.2
C15—C16—C17	120.1 (3)	O6—C3—C4	109.4 (3)
C15—C16—Cl3	120.7 (2)	O6—C3—H3A	109.8
C17—C16—Cl3	119.2 (2)	C4—C3—H3A	109.8
C8—O3—C9	111.4 (3)	O6—C3—H3B	109.8
C1—O1—C12	114.0 (3)	C4—C3—H3B	109.8
C18—C17—C16	119.5 (3)	H3A—C3—H3B	108.2
C18—C17—H17A	120.2	O2—C11—C12	113.0 (3)
C16—C17—H17A	120.2	O2—C11—H11A	109.0
C15—C14—C13	119.3 (3)	C12—C11—H11A	109.0
C15—C14—H14A	120.3	O2—C11—H11B	109.0
C13—C14—H14A	120.3	C12—C11—H11B	109.0
C11—O2—C10	113.4 (3)	H11A—C11—H11B	107.8
C6—O4—C7	112.1 (3)	O1—C12—C11	109.9 (3)
C3—O6—C2	114.4 (3)	O1—C12—H12A	109.7
C4—O5—C5	113.4 (3)	C11—C12—H12A	109.7
O1—C1—C2	109.6 (3)	O1—C12—H12B	109.7
O1—C1—H1A	109.7	C11—C12—H12B	109.7
C2—C1—H1A	109.7	H12A—C12—H12B	108.2
O1—C1—H1B	109.7	O5—C5—C6	113.9 (3)
C2—C1—H1B	109.7	O5—C5—H5A	108.8
H1A—C1—H1B	108.2	C6—C5—H5A	108.8
O3—C9—C10	108.6 (3)	O5—C5—H5B	108.8
O3—C9—H9A	110.0	C6—C5—H5B	108.8
C10—C9—H9A	110.0	H5A—C5—H5B	107.7
O3—C9—H9B	110.0	O5—C4—C3	112.3 (4)
C10—C9—H9B	110.0	O5—C4—H4A	109.1
H9A—C9—H9B	108.3	C3—C4—H4A	109.1
O2—C10—C9	108.7 (3)	O5—C4—H4B	109.1
O2—C10—H10A	109.9	C3—C4—H4B	109.1
C9—C10—H10A	109.9	H4A—C4—H4B	107.9
O2—C10—H10B	109.9	O9—Cl4—O10	121.0 (19)
C9—C10—H10B	109.9	O9—Cl4—O8	97.3 (18)
H10A—C10—H10B	108.3	O10—Cl4—O8	104.3 (15)
O4—C6—C5	108.9 (3)	O9—Cl4—O7	98.8 (15)
O4—C6—H6A	109.9	O10—Cl4—O7	99.6 (15)
C5—C6—H6A	109.9	O8—Cl4—O7	138.5 (15)
O4—C6—H6B	109.9	O8'—Cl4'—O9'	98.7 (13)
C5—C6—H6B	109.9	O8'—Cl4'—O7'	108.0 (8)
H6A—C6—H6B	108.3	O9'—Cl4'—O7'	111.9 (9)
O3—C8—C7	108.5 (3)	O8'—Cl4'—O10'	110.5 (9)
O3—C8—H8A	110.0	O9'—Cl4'—O10'	118.0 (10)
C7—C8—H8A	110.0	O7'—Cl4'—O10'	109.0 (8)

C17—C18—C13—C14	−2.6 (4)	C8—O3—C9—C10	−178.9 (3)
N1—C18—C13—C14	176.2 (2)	C11—O2—C10—C9	−175.8 (3)
C17—C18—C13—Cl1	176.8 (2)	O3—C9—C10—O2	−67.2 (4)
N1—C18—C13—Cl1	−4.4 (3)	C7—O4—C6—C5	179.2 (3)
C14—C15—C16—C17	−3.1 (4)	C9—O3—C8—C7	173.2 (3)
Cl2—C15—C16—C17	178.7 (2)	C6—O4—C7—C8	179.2 (3)
C14—C15—C16—Cl3	176.1 (2)	O3—C8—C7—O4	64.0 (4)
Cl2—C15—C16—Cl3	−2.1 (3)	C3—O6—C2—C1	176.1 (3)
C13—C18—C17—C16	2.4 (4)	O1—C1—C2—O6	59.2 (4)
N1—C18—C17—C16	−176.4 (2)	C2—O6—C3—C4	−172.0 (3)
C15—C16—C17—C18	0.4 (4)	C10—O2—C11—C12	−77.7 (4)
Cl3—C16—C17—C18	−178.8 (2)	C1—O1—C12—C11	175.7 (3)
C16—C15—C14—C13	2.9 (4)	O2—C11—C12—O1	−61.4 (4)
Cl2—C15—C14—C13	−178.8 (2)	C4—O5—C5—C6	−83.1 (4)
C18—C13—C14—C15	−0.1 (4)	O4—C6—C5—O5	−59.9 (5)
Cl1—C13—C14—C15	−179.5 (2)	C5—O5—C4—C3	179.2 (3)
C12—O1—C1—C2	175.0 (3)	O6—C3—C4—O5	−65.9 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O1ⁱ	0.89	2.13	2.916 (3)	147
N1—H1C···O6ⁱ	0.89	2.21	2.899 (3)	134
N1—H1D···O5ⁱ	0.89	2.06	2.896 (3)	156
N1—H1D···O4ⁱ	0.89	2.52	3.052 (3)	119
N1—H1E···O3ⁱ	0.89	2.19	3.046 (3)	161
N1—H1E···O2ⁱ	0.89	2.35	2.856 (3)	116

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₆H₅Cl₃N⁺·ClO₄⁻·C₁₂H₂₄O₆
M_r	561.22
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	9.4961 (19), 11.783 (2), 11.852 (2)
α, β, γ (°)	97.86 (3), 90.39 (3), 105.26 (3)
V (Å³)	1266.1 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.52
Crystal size (mm)	0.10 × 0.05 × 0.05

Data collection
Diffractometer	Rigaku Mercury2 (2x2 bin mode) diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.910, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	11310, 4713, 3562
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.152, 1.03
No. of reflections	4713
No. of parameters	346
No. of restraints	18
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.28

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O1ⁱ	0.89	2.13	2.916 (3)	147
N1—H1C···O6ⁱ	0.89	2.21	2.899 (3)	134
N1—H1D···O5ⁱ	0.89	2.06	2.896 (3)	156
N1—H1D···O4ⁱ	0.89	2.52	3.052 (3)	119
N1—H1E···O3ⁱ	0.89	2.19	3.046 (3)	161
N1—H1E···O2ⁱ	0.89	2.35	2.856 (3)	116

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

This work was supported by a Start-up Grant of Southeast University, China.

References

Fu, D.-W., Zhang, W., Cai, H.-L., Ge, J.-Z., Zhang, Y. & Xiong, R.-G. (2011). Adv. Mater. 23, 5658–5662. Web of Science CSD CrossRef CAS PubMed 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