Methyl­ammonium tetra­fluoridoborate 18-crown-6 clathrate

Jin, Y.

doi:10.1107/S1600536811054432

organic compounds

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Volume 68| Part 1| January 2012| Page o225

doi:10.1107/S1600536811054432

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Methylammonium tetrafluoridoborate 18-crown-6 clathrate

Yu Jin ^a ^*

^aOrdered Matter Science Research Center, Southeast University, Nanjing 211189, People's Republic of China
^*Correspondence e-mail: jinyunihao@yahoo.cn

(Received 3 December 2011; accepted 18 December 2011; online 23 December 2011)

In the title compound, CH₃NH₃⁺·BF₄⁻·C₁₂H₂₄O₆, the methylammonium cation makes three N—H⋯O hydrogen bonds to the 18-crown-6 molecule. The –NH₃⁺ and –CH₃ groups of the cation adopt a staggered conformation. The F atoms of the tetrafluoridoborate anion are disordered over two sets of sites in a 0.519 (11):0.481 (11) ratio. Weak C—H⋯F interactions occur in the crystal, which possibly correlate with the anion disorder.

Related literature

For related structures, see: Henschel et al. (1999 ); Trueblood et al. (1982 ). For the possible relationship of the title compound to molecular ferroelectrics, see: Wu et al. (2011 ).

Experimental

Crystal data

CH₆N⁺·BF₄⁻·C₁₂H₂₄O₆
M_r = 383.19
Monoclinic, C 2/c
a = 24.375 (5) Å
b = 8.5404 (17) Å
c = 21.345 (4) Å
β = 116.90 (3)°
V = 3962.7 (14) Å³
Z = 8
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 293 K
0.3 × 0.3 × 0.2 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.489, T_max = 1.000
19676 measured reflections
4519 independent reflections
2155 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.073
wR(F²) = 0.226
S = 1.03
4519 reflections
265 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯O2	0.89	1.98	2.867 (3)	171
N1—H1B⋯O6	0.89	1.99	2.866 (3)	168
N1—H1A⋯O4	0.89	1.99	2.876 (3)	171
C2—H2B⋯F2′ⁱ	0.97	2.41	3.345 (14)	163
C7—H7B⋯F3′	0.97	2.52	3.481 (13)	172
C9—H9B⋯F1′ⁱⁱ	0.97	2.49	3.306 (12)	142
C9—H9B⋯F2′ⁱⁱ	0.97	2.36	3.298 (17)	163
C11—H11A⋯F4′ⁱⁱⁱ	0.97	2.47	3.393 (12)	158
Symmetry codes: (i) $[x, -y+1, z-{\script{1\over 2}}]$ ; (ii) x, y+1, z; (iii) $[-x, y+1, -z+{\script{1\over 2}}]$ .

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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811054432/hb6552sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811054432/hb6552Isup2.hkl

checkCIF report

Comment top

Molecular motion has proved to cause a rotation of the local structure to give rise to the formation of reversible structural phase transition from high-temperature disordered state to low temperature ordered state. Only a small part of compounds in which the components can be arranged in a disordered status at a relative high temperature and in an ordered one at a relative low temperature have been found until now. The transition from the disordered arrangement to the ordered one results in sharp change in the physical properties of compounds (e.g. Wu et al., 2011). The protonated CH₃—NH₃⁺ cation can be easily anchored in the cavity of 18-crown-6, as a result of strong N—H···O hydrogen-bonding interactions. In the protonated CH₃—NH₃⁺, –NH₃⁺ can be fixed firmly by 18-crown-6 which is an excellent molecular-based stator via N—H···O hydrogen-bonding interactions forming a stationary axis along which the rest of CH₃—NH₃⁺ cation can rotate freely. The introduction of a disordered group in the compounds results in the potential for the order-disorder transition due to the fact that the freezing of a disordered group at low temperature forces significant orientational motions of the group and thus may induce the formation of the ferroelectric phase. As part of our search for simple ferroelectric compounds we have investigated the title compound and reported its room temperature structure.

In this crystal structure, the nitrogen of the –NH₃⁺ group lies 1.043 Å from the plane of the O atoms of the crown ring, in contrast to the analogous complex (Henschel et al., 1999) and analogous perchlorate hemihytrate (Trueblood et al., 1982), where the corresponding distance is 0.981 Å and 0.68 Å individually.

The anion and one cation are shown in Fig. 1 with the hydrogen bonds listed in Table 1. The existence of N—H···O hydrogen-bonding interactions and weak C—H···F interactions helps to make the substance more stable, and thus forms a three-dimensional structure. The components are held together by N—H···O hydrogen bonds and weak C—H···F interactions, forming a 1:1:1 aggregate. The aggregates are further connected by weak C—H···F interactions, and thus forms a complex spatial geometry.

Related literature top

For related structures, see: Henschel et al. (1999); Trueblood et al. (1982). For the possible relationship of the title compound to molecular ferroelectrics, see: Wu et al. (2011).

Experimental top

(C₁₂H₂₄O₆.CH₃NH₃⁺).(BF^-₄) was formed from a mixture of C₁₂H₂₄O₆ (264.32 mg, 1.00 mmol), CH₃NH₂ (8 mL, 40% aqueous solution), tetrafluoridoborate (10 mL, 48% aqueous solution) and distilled water (5 ml), which was stirred a few minutes at room temperature, giving a clear transparent solution. After evaporation for a few days, block colorless crystals suitable for X-ray diffraction were obtained in about 60% yield and filtered and washed with distilled water.

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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Crystal structure of the title compound with view along the c axis. Intermolecular interactions are shown as dashed lines.

Methylammonium tetrafluoroborate–1,4,7,10,13,16-hexaoxacyclooctadecane (1/1) top

Crystal data top

CH₆N⁺·BF₄⁻·C₁₂H₂₄O₆	F(000) = 1632
M_r = 383.19	D_x = 1.285 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3450 reflections
a = 24.375 (5) Å	θ = 6.2–55.3°
b = 8.5404 (17) Å	µ = 0.12 mm⁻¹
c = 21.345 (4) Å	T = 293 K
β = 116.90 (3)°	Block, colorless
V = 3962.7 (14) Å³	0.3 × 0.3 × 0.2 mm
Z = 8

Data collection top

Rigaku Mercury CCD diffractometer	4519 independent reflections
Radiation source: fine-focus sealed tube	2155 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −31→31
T_min = 0.489, T_max = 1.000	k = −11→11
19676 measured reflections	l = −27→27

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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.226	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0967P)² + 1.8449P] where P = (F_o² + 2F_c²)/3
4519 reflections	(Δ/σ)_max < 0.001
265 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

CH₆N⁺·BF₄⁻·C₁₂H₂₄O₆	V = 3962.7 (14) Å³
M_r = 383.19	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 24.375 (5) Å	µ = 0.12 mm⁻¹
b = 8.5404 (17) Å	T = 293 K
c = 21.345 (4) Å	0.3 × 0.3 × 0.2 mm
β = 116.90 (3)°

Data collection top

Rigaku Mercury CCD diffractometer	4519 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2155 reflections with I > 2σ(I)
T_min = 0.489, T_max = 1.000	R_int = 0.061
19676 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	0 restraints
wR(F²) = 0.226	H-atom parameters constrained
S = 1.03	Δρ_max = 0.25 e Å⁻³
4519 reflections	Δρ_min = −0.19 e Å⁻³
265 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	Occ. (<1)
B1	0.0812 (2)	0.6121 (6)	0.4200 (2)	0.0824 (12)
C1	0.09781 (16)	0.9413 (5)	0.04075 (16)	0.0815 (11)
H1D	0.1361	0.9848	0.0451	0.098*
H1E	0.0666	0.9547	−0.0074	0.098*
C2	0.10575 (15)	0.7737 (4)	0.05902 (16)	0.0798 (10)
H2A	0.0684	0.7324	0.0584	0.096*
H2B	0.1138	0.7162	0.0249	0.096*
C3	0.16487 (15)	0.5967 (4)	0.14898 (18)	0.0713 (9)
H3A	0.1717	0.5339	0.1153	0.086*
H3B	0.1285	0.5573	0.1513	0.086*
C4	0.21812 (15)	0.5856 (3)	0.21816 (19)	0.0710 (9)
H4A	0.2285	0.4764	0.2302	0.085*
H4B	0.2532	0.6367	0.2171	0.085*
C5	0.25467 (14)	0.6571 (4)	0.33741 (17)	0.0726 (9)
H5A	0.2888	0.7145	0.3369	0.087*
H5B	0.2679	0.5500	0.3513	0.087*
C6	0.23720 (16)	0.7287 (4)	0.38822 (16)	0.0786 (11)
H6A	0.2014	0.6757	0.3867	0.094*
H6B	0.2707	0.7183	0.4353	0.094*
C7	0.2087 (2)	0.9725 (5)	0.41965 (19)	0.0952 (12)
H7A	0.2418	0.9602	0.4668	0.114*
H7B	0.1715	0.9291	0.4185	0.114*
C8	0.1995 (2)	1.1415 (5)	0.4007 (2)	0.1035 (14)
H8A	0.1915	1.1987	0.4349	0.124*
H8B	0.2364	1.1843	0.4007	0.124*
C9	0.1367 (3)	1.3161 (4)	0.3089 (3)	0.1140 (16)
H9A	0.1722	1.3590	0.3058	0.137*
H9B	0.1294	1.3782	0.3424	0.137*
C10	0.0821 (3)	1.3234 (5)	0.2390 (3)	0.1215 (18)
H10A	0.0477	1.2691	0.2405	0.146*
H10B	0.0702	1.4316	0.2261	0.146*
C11	0.04701 (16)	1.2532 (5)	0.1191 (3)	0.1032 (15)
H11A	0.0336	1.3600	0.1049	0.124*
H11B	0.0126	1.1944	0.1183	0.124*
C12	0.06760 (16)	1.1822 (4)	0.0705 (2)	0.0937 (13)
H12A	0.0360	1.1944	0.0224	0.112*
H12B	0.1045	1.2344	0.0749	0.112*
C13	0.06353 (16)	0.8461 (5)	0.2238 (2)	0.0916 (12)
H13A	0.0719	0.7970	0.2677	0.137*
H13B	0.0485	0.7693	0.1870	0.137*
H13C	0.0331	0.9264	0.2137	0.137*
F1	0.0811 (5)	0.6402 (13)	0.3601 (5)	0.131 (3)	0.481 (11)
F2	0.1331 (3)	0.5661 (14)	0.4620 (5)	0.165 (5)	0.481 (11)
F3	0.1255 (7)	0.705 (3)	0.4670 (9)	0.198 (8)	0.481 (11)
F4	0.0293 (5)	0.6160 (16)	0.4217 (8)	0.156 (5)	0.481 (11)
F1'	0.0550 (4)	0.5665 (13)	0.3505 (4)	0.128 (3)	0.519 (11)
F2'	0.1037 (8)	0.4578 (13)	0.4316 (7)	0.245 (7)	0.519 (11)
F3'	0.0814 (5)	0.7788 (7)	0.4154 (6)	0.131 (3)	0.519 (11)
F4'	0.0385 (5)	0.5822 (11)	0.4440 (7)	0.134 (4)	0.519 (11)
N1	0.12000 (9)	0.9158 (2)	0.22837 (11)	0.0495 (6)
H1A	0.1325	0.9917	0.2604	0.074*
H1B	0.1128	0.9553	0.1868	0.074*
H1C	0.1491	0.8427	0.2408	0.074*
O1	0.15612 (9)	0.7548 (2)	0.12755 (10)	0.0627 (6)
O2	0.20466 (8)	0.6585 (2)	0.27007 (10)	0.0589 (5)
O3	0.22339 (9)	0.8921 (2)	0.37129 (10)	0.0678 (6)
O4	0.14840 (12)	1.1580 (3)	0.33206 (15)	0.0861 (8)
O5	0.09714 (10)	1.2516 (2)	0.18839 (14)	0.0836 (7)
O6	0.07986 (9)	1.0197 (3)	0.08667 (11)	0.0745 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
B1	0.093 (4)	0.091 (4)	0.079 (3)	−0.017 (3)	0.052 (3)	−0.021 (3)
C1	0.077 (2)	0.108 (3)	0.0402 (17)	−0.023 (2)	0.0092 (16)	0.0027 (17)
C2	0.072 (2)	0.099 (3)	0.0504 (18)	−0.0180 (19)	0.0124 (17)	−0.0165 (18)
C3	0.072 (2)	0.0590 (19)	0.086 (2)	0.0001 (16)	0.0379 (19)	−0.0157 (17)
C4	0.074 (2)	0.0512 (17)	0.102 (3)	0.0160 (15)	0.052 (2)	−0.0005 (17)
C5	0.0608 (19)	0.0652 (19)	0.072 (2)	0.0068 (15)	0.0130 (17)	0.0232 (16)
C6	0.080 (2)	0.079 (2)	0.0510 (18)	−0.0188 (18)	0.0075 (17)	0.0282 (17)
C7	0.113 (3)	0.119 (3)	0.062 (2)	−0.033 (3)	0.047 (2)	−0.015 (2)
C8	0.140 (4)	0.108 (3)	0.087 (3)	−0.042 (3)	0.072 (3)	−0.049 (2)
C9	0.170 (5)	0.060 (2)	0.163 (5)	0.000 (3)	0.119 (4)	−0.030 (3)
C10	0.143 (4)	0.060 (2)	0.209 (6)	0.039 (3)	0.121 (5)	0.017 (3)
C11	0.053 (2)	0.070 (2)	0.160 (4)	0.0206 (18)	0.025 (3)	0.047 (3)
C12	0.0542 (19)	0.087 (3)	0.100 (3)	0.0011 (19)	0.000 (2)	0.055 (2)
C13	0.071 (2)	0.091 (3)	0.121 (3)	−0.0077 (19)	0.051 (2)	0.014 (2)
F1	0.164 (8)	0.154 (8)	0.084 (5)	−0.001 (5)	0.064 (6)	0.024 (5)
F2	0.077 (4)	0.167 (9)	0.153 (7)	−0.012 (5)	−0.035 (4)	0.070 (6)
F3	0.143 (9)	0.293 (16)	0.188 (12)	−0.136 (11)	0.102 (9)	−0.138 (13)
F4	0.087 (5)	0.236 (12)	0.166 (9)	−0.025 (5)	0.076 (5)	−0.021 (7)
F1'	0.125 (6)	0.157 (8)	0.095 (4)	0.004 (4)	0.044 (4)	−0.051 (5)
F2'	0.445 (18)	0.148 (8)	0.296 (12)	0.147 (10)	0.302 (14)	0.114 (8)
F3'	0.156 (7)	0.091 (4)	0.154 (6)	−0.039 (4)	0.077 (6)	−0.006 (4)
F4'	0.207 (10)	0.103 (4)	0.173 (8)	−0.099 (6)	0.156 (8)	−0.088 (5)
N1	0.0497 (12)	0.0450 (12)	0.0531 (13)	0.0062 (10)	0.0227 (11)	0.0051 (10)
O1	0.0595 (12)	0.0602 (13)	0.0624 (13)	−0.0057 (9)	0.0223 (10)	−0.0088 (10)
O2	0.0451 (10)	0.0542 (11)	0.0685 (13)	0.0106 (8)	0.0178 (10)	0.0096 (9)
O3	0.0808 (14)	0.0767 (14)	0.0451 (11)	−0.0172 (11)	0.0277 (10)	0.0049 (10)
O4	0.115 (2)	0.0612 (14)	0.110 (2)	−0.0184 (13)	0.0749 (18)	−0.0261 (13)
O5	0.0680 (14)	0.0553 (13)	0.130 (2)	0.0189 (11)	0.0476 (15)	0.0133 (13)
O6	0.0686 (14)	0.0717 (14)	0.0649 (13)	−0.0036 (11)	0.0140 (11)	0.0222 (11)

Geometric parameters (Å, º) top

B1—F2	1.238 (8)	C7—O3	1.414 (4)
B1—F4	1.281 (11)	C7—C8	1.489 (6)
B1—F1	1.299 (9)	C7—H7A	0.9700
B1—F3	1.348 (8)	C7—H7B	0.9700
B1—F4'	1.376 (10)	C8—O4	1.437 (5)
B1—F1'	1.380 (8)	C8—H8A	0.9700
B1—F2'	1.406 (9)	C8—H8B	0.9700
B1—F3'	1.428 (7)	C9—O4	1.422 (5)
C1—O6	1.410 (4)	C9—C10	1.486 (7)
C1—C2	1.474 (5)	C9—H9A	0.9700
C1—H1D	0.9700	C9—H9B	0.9700
C1—H1E	0.9700	C10—O5	1.427 (5)
C2—O1	1.431 (4)	C10—H10A	0.9700
C2—H2A	0.9700	C10—H10B	0.9700
C2—H2B	0.9700	C11—O5	1.430 (5)
C3—O1	1.411 (3)	C11—C12	1.473 (6)
C3—C4	1.463 (5)	C11—H11A	0.9700
C3—H3A	0.9700	C11—H11B	0.9700
C3—H3B	0.9700	C12—O6	1.429 (4)
C4—O2	1.432 (3)	C12—H12A	0.9700
C4—H4A	0.9700	C12—H12B	0.9700
C4—H4B	0.9700	C13—N1	1.461 (4)
C5—O2	1.402 (3)	C13—H13A	0.9600
C5—C6	1.466 (5)	C13—H13B	0.9600
C5—H5A	0.9700	C13—H13C	0.9600
C5—H5B	0.9700	N1—H1A	0.8900
C6—O3	1.443 (4)	N1—H1B	0.8900
C6—H6A	0.9700	N1—H1C	0.8900
C6—H6B	0.9700

F2—B1—F4	133.3 (10)	O3—C6—H6A	109.8
F2—B1—F1	108.5 (8)	C5—C6—H6A	109.8
F4—B1—F1	117.4 (9)	O3—C6—H6B	109.8
F2—B1—F3	55.5 (12)	C5—C6—H6B	109.8
F4—B1—F3	115.6 (8)	H6A—C6—H6B	108.3
F1—B1—F3	105.5 (7)	O3—C7—C8	109.2 (3)
F2—B1—F4'	111.6 (8)	O3—C7—H7A	109.8
F4—B1—F4'	21.9 (12)	C8—C7—H7A	109.8
F1—B1—F4'	137.4 (8)	O3—C7—H7B	109.8
F3—B1—F4'	108.6 (6)	C8—C7—H7B	109.8
F2—B1—F1'	120.9 (8)	H7A—C7—H7B	108.3
F4—B1—F1'	93.2 (8)	O4—C8—C7	109.0 (3)
F1—B1—F1'	36.9 (4)	O4—C8—H8A	109.9
F3—B1—F1'	142.3 (7)	C7—C8—H8A	109.9
F4'—B1—F1'	106.7 (6)	O4—C8—H8B	109.9
F2—B1—F2'	52.0 (7)	C7—C8—H8B	109.9
F4—B1—F2'	109.4 (10)	H8A—C8—H8B	108.3
F1—B1—F2'	100.0 (6)	O4—C9—C10	109.7 (4)
F3—B1—F2'	107.4 (16)	O4—C9—H9A	109.7
F4'—B1—F2'	93.6 (8)	C10—C9—H9A	109.7
F1'—B1—F2'	83.0 (9)	O4—C9—H9B	109.7
F2—B1—F3'	109.4 (8)	C10—C9—H9B	109.7
F4—B1—F3'	90.6 (7)	H9A—C9—H9B	108.2
F1—B1—F3'	75.4 (6)	O5—C10—C9	108.8 (3)
F3—B1—F3'	55.9 (9)	O5—C10—H10A	109.9
F4'—B1—F3'	103.7 (6)	C9—C10—H10A	109.9
F1'—B1—F3'	102.9 (6)	O5—C10—H10B	109.9
F2'—B1—F3'	159.0 (10)	C9—C10—H10B	109.9
O6—C1—C2	108.8 (3)	H10A—C10—H10B	108.3
O6—C1—H1D	109.9	O5—C11—C12	108.7 (3)
C2—C1—H1D	109.9	O5—C11—H11A	109.9
O6—C1—H1E	109.9	C12—C11—H11A	109.9
C2—C1—H1E	109.9	O5—C11—H11B	109.9
H1D—C1—H1E	108.3	C12—C11—H11B	109.9
O1—C2—C1	109.2 (2)	H11A—C11—H11B	108.3
O1—C2—H2A	109.8	O6—C12—C11	109.2 (3)
C1—C2—H2A	109.8	O6—C12—H12A	109.8
O1—C2—H2B	109.8	C11—C12—H12A	109.8
C1—C2—H2B	109.8	O6—C12—H12B	109.8
H2A—C2—H2B	108.3	C11—C12—H12B	109.8
O1—C3—C4	108.9 (2)	H12A—C12—H12B	108.3
O1—C3—H3A	109.9	N1—C13—H13A	109.5
C4—C3—H3A	109.9	N1—C13—H13B	109.5
O1—C3—H3B	109.9	H13A—C13—H13B	109.5
C4—C3—H3B	109.9	N1—C13—H13C	109.5
H3A—C3—H3B	108.3	H13A—C13—H13C	109.5
O2—C4—C3	110.1 (2)	H13B—C13—H13C	109.5
O2—C4—H4A	109.6	C13—N1—H1A	109.5
C3—C4—H4A	109.6	C13—N1—H1B	109.5
O2—C4—H4B	109.6	H1A—N1—H1B	109.5
C3—C4—H4B	109.6	C13—N1—H1C	109.5
H4A—C4—H4B	108.2	H1A—N1—H1C	109.5
O2—C5—C6	110.2 (3)	H1B—N1—H1C	109.5
O2—C5—H5A	109.6	C3—O1—C2	111.9 (2)
C6—C5—H5A	109.6	C5—O2—C4	113.1 (2)
O2—C5—H5B	109.6	C7—O3—C6	113.2 (3)
C6—C5—H5B	109.6	C9—O4—C8	113.1 (3)
H5A—C5—H5B	108.1	C10—O5—C11	112.7 (3)
O3—C6—C5	109.3 (2)	C1—O6—C12	112.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O2	0.89	1.98	2.867 (3)	171
N1—H1B···O6	0.89	1.99	2.866 (3)	168
N1—H1A···O4	0.89	1.99	2.876 (3)	171
C2—H2B···F2′ⁱ	0.97	2.41	3.345 (14)	163
C7—H7B···F3′	0.97	2.52	3.481 (13)	172
C9—H9B···F1′ⁱⁱ	0.97	2.49	3.306 (12)	142
C9—H9B···F2′ⁱⁱ	0.97	2.36	3.298 (17)	163
C11—H11A···F4′ⁱⁱⁱ	0.97	2.47	3.393 (12)	158

Symmetry codes: (i) x, −y+1, z−1/2; (ii) x, y+1, z; (iii) −x, y+1, −z+1/2.

Experimental details

Crystal data
Chemical formula	CH₆N⁺·BF₄⁻·C₁₂H₂₄O₆
M_r	383.19
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	24.375 (5), 8.5404 (17), 21.345 (4)
β (°)	116.90 (3)
V (Å³)	3962.7 (14)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.3 × 0.3 × 0.2

Data collection
Diffractometer	Rigaku Mercury CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.489, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	19676, 4519, 2155
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.226, 1.03
No. of reflections	4519
No. of parameters	265
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.19

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···O2	0.89	1.98	2.867 (3)	171
N1—H1B···O6	0.89	1.99	2.866 (3)	168
N1—H1A···O4	0.89	1.99	2.876 (3)	171
C2—H2B···F2'ⁱ	0.97	2.41	3.345 (14)	163
C7—H7B···F3'	0.97	2.52	3.481 (13)	172
C9—H9B···F1'ⁱⁱ	0.97	2.49	3.306 (12)	142
C9—H9B···F2'ⁱⁱ	0.97	2.36	3.298 (17)	163
C11—H11A···F4'ⁱⁱⁱ	0.97	2.47	3.393 (12)	158

Symmetry codes: (i) x, −y+1, z−1/2; (ii) x, y+1, z; (iii) −x, y+1, −z+1/2.

Acknowledgements

The author thanks Southeast University for support.

References

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