2-Methyl-piperidinium bromide.

In the title organic-inorganic hybrid salt, C(6)H(14)N(+)·Br(-), N-H⋯Br hydrogen bonds link the cations and anions, forming extended hydrogen-bonded chains along the c axis.

Related literature

For general background to ferroelectric organic frameworks, see: Ye et al. (2006 ▶); Zhang et al. (2008 ▶, 2010 ▶).

Experimental

Crystal data

C6H14N+·Br−

M = 180.09

Orthorhombic,

a = 22.137 (4) Å

b = 9.918 (2) Å

c = 7.5853 (15) Å

V = 1665.5 (6) Å3

Z = 8

Mo Kα radiation

μ = 4.85 mm−1

T = 293 K

0.55 × 0.44 × 0.36 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.134, T max = 0.223

15678 measured reflections

1907 independent reflections

1142 reflections with I > 2σ(I)

R int = 0.109

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.118

S = 1.05

1907 reflections

75 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.48 e Å−3

Data collection: SCXmini (Rigaku, 2006 ▶); cell refinement: SCXmini; data reduction: SCXmini; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812022878/fy2056sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022878/fy2056Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812022878/fy2056Isup3.cml

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

C6H14N+·Br−	F(000) = 736
Mr = 180.09	Dx = 1.436 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 3638 reflections
a = 22.137 (4) Å	θ = 3.0–27.5°
b = 9.918 (2) Å	µ = 4.85 mm−1
c = 7.5853 (15) Å	T = 293 K
V = 1665.5 (6) Å3	Block, colorless
Z = 8	0.55 × 0.44 × 0.36 mm

Rigaku SCXmini diffractometer	1907 independent reflections
Radiation source: fine-focus sealed tube	1142 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.109
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.4°
ω scans	h = −28→28
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −12→12
Tmin = 0.134, Tmax = 0.223	l = −9→9
15678 measured reflections

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)] = 0.049	H-atom parameters constrained
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.0407P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
1907 reflections	Δρmax = 0.38 e Å−3
75 parameters	Δρmin = −0.48 e Å−3
0 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: 0.0022 (5)

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
C1	0.6672 (2)	0.7098 (5)	0.0449 (6)	0.0546 (13)
H1	0.6680	0.6902	0.1715	0.065*
C2	0.6608 (3)	0.8597 (6)	0.0205 (7)	0.0817 (19)
H2A	0.6633	0.8808	−0.1041	0.098*
H2B	0.6939	0.9049	0.0797	0.098*
C3	0.6018 (3)	0.9124 (6)	0.0922 (8)	0.097 (2)
H3A	0.6007	0.8994	0.2189	0.117*
H3B	0.5988	1.0082	0.0686	0.117*
C4	0.5503 (3)	0.8414 (6)	0.0099 (7)	0.0799 (18)
H4A	0.5128	0.8733	0.0615	0.096*
H4B	0.5494	0.8611	−0.1153	0.096*
C5	0.5556 (2)	0.6950 (5)	0.0365 (6)	0.0594 (13)
H5A	0.5226	0.6497	−0.0231	0.071*
H5B	0.5528	0.6747	0.1613	0.071*
C6	0.7220 (2)	0.6499 (6)	−0.0376 (8)	0.104 (2)
H6A	0.7210	0.5536	−0.0242	0.156*
H6B	0.7575	0.6850	0.0189	0.156*
H6C	0.7229	0.6722	−0.1607	0.156*
N1	0.61363 (14)	0.6448 (4)	−0.0327 (4)	0.0436 (9)
H1A	0.6158	0.5554	−0.0128	0.052*
H1B	0.6143	0.6574	−0.1502	0.052*
Br1	0.61324 (2)	0.32302 (5)	0.03937 (6)	0.0540 (2)

	U11	U22	U33	U12	U13	U23
C1	0.055 (3)	0.060 (3)	0.049 (3)	−0.010 (2)	−0.014 (2)	0.001 (2)
C2	0.100 (5)	0.071 (4)	0.075 (4)	−0.040 (4)	−0.030 (4)	0.017 (3)
C3	0.160 (7)	0.043 (3)	0.088 (5)	0.015 (4)	0.003 (5)	−0.002 (3)
C4	0.095 (5)	0.062 (4)	0.082 (4)	0.027 (3)	0.012 (3)	0.004 (3)
C5	0.050 (3)	0.060 (3)	0.068 (3)	0.008 (2)	0.013 (2)	0.003 (3)
C6	0.046 (4)	0.143 (6)	0.121 (6)	0.003 (3)	0.000 (3)	0.027 (4)
N1	0.048 (2)	0.041 (2)	0.042 (2)	0.0030 (16)	0.0024 (18)	0.0000 (16)
Br1	0.0752 (4)	0.0440 (3)	0.0427 (3)	0.0012 (2)	−0.0015 (2)	−0.0005 (2)

C1—N1	1.473 (5)	C4—H4A	0.9700
C1—C6	1.488 (7)	C4—H4B	0.9700
C1—C2	1.504 (7)	C5—N1	1.475 (5)
C1—H1	0.9800	C5—H5A	0.9700
C2—C3	1.507 (8)	C5—H5B	0.9700
C2—H2A	0.9700	C6—H6A	0.9600
C2—H2B	0.9700	C6—H6B	0.9600
C3—C4	1.478 (8)	C6—H6C	0.9600
C3—H3A	0.9700	N1—H1A	0.9000
C3—H3B	0.9700	N1—H1B	0.9000
C4—C5	1.471 (6)
N1—C1—C6	108.2 (4)	C5—C4—H4B	109.5
N1—C1—C2	107.9 (4)	C3—C4—H4B	109.5
C6—C1—C2	114.9 (4)	H4A—C4—H4B	108.1
N1—C1—H1	108.6	C4—C5—N1	110.7 (4)
C6—C1—H1	108.6	C4—C5—H5A	109.5
C2—C1—H1	108.6	N1—C5—H5A	109.5
C1—C2—C3	112.4 (4)	C4—C5—H5B	109.5
C1—C2—H2A	109.1	N1—C5—H5B	109.5
C3—C2—H2A	109.1	H5A—C5—H5B	108.1
C1—C2—H2B	109.1	C1—C6—H6A	109.5
C3—C2—H2B	109.1	C1—C6—H6B	109.5
H2A—C2—H2B	107.9	H6A—C6—H6B	109.5
C4—C3—C2	110.5 (5)	C1—C6—H6C	109.5
C4—C3—H3A	109.5	H6A—C6—H6C	109.5
C2—C3—H3A	109.5	H6B—C6—H6C	109.5
C4—C3—H3B	109.5	C1—N1—C5	114.3 (4)
C2—C3—H3B	109.5	C1—N1—H1A	108.7
H3A—C3—H3B	108.1	C5—N1—H1A	108.7
C5—C4—C3	110.5 (5)	C1—N1—H1B	108.7
C5—C4—H4A	109.5	C5—N1—H1B	108.7
C3—C4—H4A	109.5	H1A—N1—H1B	107.6

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Br1	0.90	2.34	3.238 (4)	176
N1—H1B···Br1i	0.90	2.36	3.262 (3)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Br1	0.90	2.34	3.238 (4)	176
N1—H1B⋯Br1i	0.90	2.36	3.262 (3)	176

Symmetry code: (i) .