1,1'-Dimethyl-1,1'-(butane-1,4-di-yl)dipyrrolidinium dibromide methanol disolvate.

In the title compound, C(14)H(30)N(2) (2+)·2Br(-)·2CH(3)OH, two terminal C atoms of the butane chain are connected to two N atoms of the 1-methyl-pyrollidines, forming a linear diquaternary ammonium cation. The cation lies across a centre of inversion located between the two central C atoms of the butane chain. The asymmetric unit therefore comprises one half-cation, a bromide anion and a methanol solvent mol-ecule. In the crystal structure, the bromide anions are linked to the methanol solvent mol-ecules by O-H⋯Br hydrogen bonds.

Related literature

For information on the use of organic amines in zeolite synthesis, see: Gramm et al. (2006 ▶); Hong et al. (2007 ▶). For a previous synthesis of the title compound, see: Hong et al. (2004 ▶).

Experimental

Crystal data

C14H30N2 2+·2Br−·2CH4O

M = 450.30

Monoclinic,

a = 6.4919 (7) Å

b = 12.4861 (13) Å

c = 12.9683 (13) Å

β = 90.748 (2)°

V = 1051.10 (19) Å3

Z = 2

Mo Kα radiation

μ = 3.87 mm−1

T = 193 (2) K

0.30 × 0.25 × 0.24 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.390, T max = 0.457 (expected range = 0.337–0.396)

5618 measured reflections

2013 independent reflections

1681 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.067

S = 1.09

2013 reflections

102 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 1997 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808000172/sj2458sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808000172/sj2458Isup2.hkl

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

C14H30N22+·2Br–·2CH4O	F000 = 468
Mr = 450.30	Dx = 1.423 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5618 reflections
a = 6.4919 (7) Å	θ = 2.3–26.0º
b = 12.4861 (13) Å	µ = 3.87 mm−1
c = 12.9683 (13) Å	T = 193 (2) K
β = 90.748 (2)º	Block, colorless
V = 1051.10 (19) Å3	0.30 × 0.25 × 0.24 mm
Z = 2

Bruker SMART APEX CCD area-detector diffractometer	2013 independent reflections
Radiation source: fine-focus sealed tube	1681 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.022
T = 193(2) K	θmax = 26.0º
φ and ω scans	θmin = 2.3º
Absorption correction: multi-scan(SADABS; Bruker, 2000)	h = −5→8
Tmin = 0.390, Tmax = 0.457	k = −14→15
5618 measured reflections	l = −15→16

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)] = 0.027	H-atom parameters constrained
wR(F2) = 0.067	w = 1/[σ2(Fo2) + (0.0335P)2 + 0.1193P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
2013 reflections	Δρmax = 0.42 e Å−3
102 parameters	Δρmin = −0.20 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
Br1	0.22798 (4)	0.222545 (19)	0.645609 (19)	0.03899 (11)
N1	0.6827 (3)	0.01906 (14)	0.77454 (14)	0.0279 (4)
C1	0.8754 (4)	−0.04680 (19)	0.79320 (18)	0.0380 (6)
H1A	0.8411	−0.1171	0.8198	0.046*
H1B	0.9671	−0.0113	0.8420	0.046*
C2	0.9755 (4)	−0.0559 (2)	0.68752 (18)	0.0443 (7)
H2A	1.0286	−0.1276	0.6772	0.053*
H2B	1.0884	−0.0054	0.6820	0.053*
C3	0.8074 (4)	−0.0306 (2)	0.60735 (19)	0.0467 (7)
H3A	0.8386	0.0351	0.5708	0.056*
H3B	0.7939	−0.0884	0.5577	0.056*
C4	0.6110 (4)	−0.0184 (2)	0.66926 (17)	0.0385 (6)
H4A	0.5197	0.0339	0.6375	0.046*
H4B	0.5390	−0.0862	0.6741	0.046*
C5	0.5187 (3)	−0.00229 (18)	0.85296 (17)	0.0316 (5)
H5A	0.4768	−0.0767	0.8475	0.038*
H5B	0.3994	0.0415	0.8364	0.038*
C6	0.5842 (3)	0.01998 (18)	0.96372 (16)	0.0319 (5)
H6A	0.6052	0.0962	0.9734	0.038*
H6B	0.7129	−0.0164	0.9792	0.038*
C7	0.7340 (4)	0.13607 (17)	0.77065 (18)	0.0344 (5)
H7A	0.7800	0.1595	0.8376	0.052*
H7B	0.6137	0.1759	0.7503	0.052*
H7C	0.8412	0.1477	0.7216	0.052*
O1	0.5324 (3)	0.32947 (15)	0.47786 (14)	0.0510 (5)
H1	0.4456	0.3057	0.5171	0.076*
C8	0.6858 (4)	0.2517 (2)	0.4620 (2)	0.0478 (7)
H8A	0.7952	0.2615	0.5116	0.072*
H8B	0.7392	0.2590	0.3937	0.072*
H8C	0.6275	0.1816	0.4700	0.072*

	U11	U22	U33	U12	U13	U23
Br1	0.03054 (16)	0.03698 (16)	0.04954 (18)	0.00222 (11)	0.00417 (11)	0.00310 (11)
N1	0.0241 (10)	0.0302 (9)	0.0296 (10)	0.0005 (8)	0.0036 (8)	−0.0010 (8)
C1	0.0336 (13)	0.0414 (14)	0.0390 (14)	0.0110 (11)	0.0052 (11)	0.0050 (11)
C2	0.0438 (16)	0.0413 (14)	0.0482 (16)	0.0130 (12)	0.0163 (13)	0.0038 (12)
C3	0.0487 (16)	0.0560 (17)	0.0359 (14)	0.0039 (14)	0.0113 (13)	−0.0063 (12)
C4	0.0396 (14)	0.0453 (14)	0.0307 (12)	−0.0027 (12)	−0.0011 (11)	−0.0059 (11)
C5	0.0243 (12)	0.0349 (12)	0.0359 (13)	−0.0060 (10)	0.0079 (10)	−0.0032 (10)
C6	0.0265 (12)	0.0337 (12)	0.0356 (13)	−0.0031 (10)	0.0072 (10)	−0.0019 (10)
C7	0.0318 (13)	0.0308 (12)	0.0406 (14)	−0.0050 (10)	0.0041 (11)	0.0040 (10)
O1	0.0450 (12)	0.0590 (12)	0.0492 (12)	0.0083 (10)	0.0092 (9)	0.0080 (9)
C8	0.0447 (17)	0.0497 (15)	0.0492 (17)	0.0009 (13)	0.0048 (14)	−0.0040 (12)

N1—C7	1.500 (3)	C5—C6	1.518 (3)
N1—C5	1.506 (3)	C5—H5A	0.9700
N1—C4	1.511 (3)	C5—H5B	0.9700
N1—C1	1.514 (3)	C6—C6i	1.535 (4)
C1—C2	1.528 (3)	C6—H6A	0.9700
C1—H1A	0.9700	C6—H6B	0.9700
C1—H1B	0.9700	C7—H7A	0.9600
C2—C3	1.530 (4)	C7—H7B	0.9600
C2—H2A	0.9700	C7—H7C	0.9600
C2—H2B	0.9700	O1—C8	1.408 (3)
C3—C4	1.523 (3)	O1—H1	0.8200
C3—H3A	0.9700	C8—H8A	0.9600
C3—H3B	0.9700	C8—H8B	0.9600
C4—H4A	0.9700	C8—H8C	0.9600
C4—H4B	0.9700
C7—N1—C5	110.76 (17)	C3—C4—H4B	110.8
C7—N1—C4	109.70 (18)	H4A—C4—H4B	108.8
C5—N1—C4	110.08 (17)	N1—C5—C6	114.51 (17)
C7—N1—C1	110.55 (18)	N1—C5—H5A	108.6
C5—N1—C1	112.72 (17)	C6—C5—H5A	108.6
C4—N1—C1	102.75 (17)	N1—C5—H5B	108.6
N1—C1—C2	104.89 (18)	C6—C5—H5B	108.6
N1—C1—H1A	110.8	H5A—C5—H5B	107.6
C2—C1—H1A	110.8	C5—C6—C6i	109.1 (2)
N1—C1—H1B	110.8	C5—C6—H6A	109.9
C2—C1—H1B	110.8	C6i—C6—H6A	109.9
H1A—C1—H1B	108.8	C5—C6—H6B	109.9
C1—C2—C3	106.6 (2)	C6i—C6—H6B	109.9
C1—C2—H2A	110.4	H6A—C6—H6B	108.3
C3—C2—H2A	110.4	N1—C7—H7A	109.5
C1—C2—H2B	110.4	N1—C7—H7B	109.5
C3—C2—H2B	110.4	H7A—C7—H7B	109.5
H2A—C2—H2B	108.6	N1—C7—H7C	109.5
C4—C3—C2	104.9 (2)	H7A—C7—H7C	109.5
C4—C3—H3A	110.8	H7B—C7—H7C	109.5
C2—C3—H3A	110.8	C8—O1—H1	109.5
C4—C3—H3B	110.8	O1—C8—H8A	109.5
C2—C3—H3B	110.8	O1—C8—H8B	109.5
H3A—C3—H3B	108.8	H8A—C8—H8B	109.5
N1—C4—C3	104.9 (2)	O1—C8—H8C	109.5
N1—C4—H4A	110.8	H8A—C8—H8C	109.5
C3—C4—H4A	110.8	H8B—C8—H8C	109.5
N1—C4—H4B	110.8

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Br1	0.82	2.43	3.2453 (18)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯Br1	0.82	2.43	3.2453 (18)	172