catena-Poly[4-methyl-morpholin-4-ium [[dichloridobismuth(III)]-di-μ-chlorido]].

The asymmetric unit of the title complex, {(C(5)H(12)NO)[BiCl(4)]}(n), contains two bridging and two cis non-bridging chloride ligands coordinated to a central Bi(III) atom, and one 4-methyl-morpholin-4-ium cation. The Bi(III) atoms are linked by the bridging chloride ligands into linear chains parallel to the c axis. The chloride ions create a pseudo-octa-hedral geometry about each Bi(III) atom. Bifurcated N-H⋯Cl hydrogen bonds link the cations to the anionic chains.

Related literature

For the structures of related amino compounds, see: Turnbull (2007 ▶). For the ferroelectric properties of related amino derivatives, see: Fu et al. (2011a ▶,b ▶,c ▶).

Experimental

Crystal data

(C5H12NO)[BiCl4]

M = 452.94

Monoclinic,

a = 18.166 (4) Å

b = 9.801 (2) Å

c = 13.915 (3) Å

β = 93.36 (3)°

V = 2473.2 (9) Å3

Z = 8

Mo Kα radiation

μ = 15.08 mm−1

T = 298 K

0.10 × 0.05 × 0.05 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.428, T max = 0.470

12468 measured reflections

2830 independent reflections

2437 reflections with I > 2σ(I)

R int = 0.090

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.088

S = 1.14

2830 reflections

111 parameters

H-atom parameters constrained

Δρmax = 2.45 e Å−3

Δρmin = −1.44 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812001717/pk2380sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812001717/pk2380Isup2.hkl

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

(C5H12NO)[BiCl4]	F(000) = 1664
Mr = 452.94	Dx = 2.433 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2830 reflections
a = 18.166 (4) Å	θ = 3.6–27.5°
b = 9.801 (2) Å	µ = 15.08 mm−1
c = 13.915 (3) Å	T = 298 K
β = 93.36 (3)°	Block, colorless
V = 2473.2 (9) Å3	0.10 × 0.05 × 0.05 mm
Z = 8

Rigaku Mercury2 diffractometer	2830 independent reflections
Radiation source: fine-focus sealed tube	2437 reflections with I > 2σ(I)
graphite	Rint = 0.090
Detector resolution: 13.7 pixels mm-1	θmax = 27.5°, θmin = 3.6°
CCD profile fitting scans	h = −23→23
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −12→12
Tmin = 0.428, Tmax = 0.470	l = −18→18
12468 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)] = 0.037	H-atom parameters constrained
wR(F2) = 0.088	w = 1/[σ2(Fo2) + (0.015P)2 + 5.1391P] where P = (Fo2 + 2Fc2)/3
S = 1.14	(Δ/σ)max < 0.001
2830 reflections	Δρmax = 2.45 e Å−3
111 parameters	Δρmin = −1.44 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: 0.0095 (2)

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.

	x	y	z	Uiso*/Ueq
Bi1	0.038523 (12)	0.36337 (2)	−0.101352 (17)	0.02581 (15)
Cl4	−0.02461 (14)	0.3417 (2)	0.06880 (17)	0.0494 (6)
Cl3	−0.10115 (11)	0.3718 (2)	−0.22296 (15)	0.0407 (5)
Cl2	0.02635 (11)	0.1057 (2)	−0.11236 (16)	0.0438 (5)
Cl1	0.16693 (12)	0.3571 (2)	−0.02381 (18)	0.0568 (7)
N1	0.1587 (3)	0.9444 (6)	0.1521 (4)	0.0342 (14)
H1	0.1239	0.9003	0.1835	0.041*
O1	0.1918 (3)	1.1380 (6)	0.3004 (5)	0.0564 (18)
C2	0.2251 (4)	0.9334 (8)	0.2192 (6)	0.045 (2)
H2A	0.2371	0.8380	0.2299	0.054*
H2B	0.2667	0.9766	0.1907	0.054*
C1	0.2122 (4)	0.9995 (9)	0.3123 (5)	0.046 (2)
H1B	0.1735	0.9510	0.3432	0.055*
H1C	0.2568	0.9938	0.3540	0.055*
C4	0.1376 (5)	1.0896 (9)	0.1428 (6)	0.049 (2)
H4A	0.1754	1.1389	0.1106	0.058*
H4B	0.0917	1.0974	0.1040	0.058*
C5	0.1287 (5)	1.1502 (9)	0.2384 (8)	0.059 (3)
H5A	0.1166	1.2461	0.2305	0.070*
H5B	0.0878	1.1060	0.2675	0.070*
C3	0.1707 (6)	0.8803 (10)	0.0586 (8)	0.075 (3)
H3A	0.1258	0.8837	0.0185	0.113*
H3B	0.1852	0.7869	0.0685	0.113*
H3C	0.2088	0.9284	0.0277	0.113*

	U11	U22	U33	U12	U13	U23
Bi1	0.0243 (2)	0.0229 (2)	0.0303 (2)	0.00046 (9)	0.00217 (12)	−0.00330 (11)
Cl4	0.0746 (15)	0.0284 (11)	0.0480 (12)	−0.0059 (9)	0.0276 (11)	−0.0025 (9)
Cl3	0.0254 (10)	0.0589 (15)	0.0384 (11)	0.0057 (7)	0.0067 (8)	0.0025 (9)
Cl2	0.0409 (11)	0.0212 (10)	0.0692 (15)	0.0001 (8)	0.0033 (10)	−0.0040 (10)
Cl1	0.0340 (12)	0.0697 (18)	0.0647 (15)	−0.0136 (9)	−0.0135 (10)	0.0200 (11)
N1	0.035 (3)	0.036 (4)	0.033 (3)	−0.012 (3)	0.010 (2)	0.003 (3)
O1	0.052 (4)	0.049 (4)	0.068 (4)	−0.010 (3)	−0.003 (3)	−0.010 (3)
C2	0.029 (4)	0.033 (5)	0.071 (6)	0.001 (3)	−0.002 (4)	0.006 (4)
C1	0.040 (5)	0.058 (6)	0.040 (5)	−0.011 (4)	0.002 (3)	0.007 (4)
C4	0.050 (5)	0.037 (5)	0.058 (6)	−0.003 (4)	−0.004 (4)	0.021 (5)
C5	0.043 (6)	0.046 (6)	0.088 (8)	0.005 (4)	0.009 (5)	0.018 (5)
C3	0.080 (8)	0.070 (8)	0.078 (8)	−0.035 (5)	0.018 (6)	−0.012 (6)

Bi1—Cl1	2.513 (2)	C2—C1	1.480 (11)
Bi1—Cl2	2.539 (2)	C2—H2A	0.9700
Bi1—Cl4	2.699 (2)	C2—H2B	0.9700
Bi1—Cl3i	2.758 (2)	C1—H1B	0.9700
Bi1—Cl4ii	2.939 (2)	C1—H1C	0.9700
Bi1—Cl3	2.967 (2)	C4—C5	1.475 (13)
Cl4—Bi1ii	2.939 (2)	C4—H4A	0.9700
Cl3—Bi1i	2.758 (2)	C4—H4B	0.9700
N1—C3	1.473 (12)	C5—H5A	0.9700
N1—C4	1.476 (9)	C5—H5B	0.9700
N1—C2	1.486 (9)	C3—H3A	0.9600
N1—H1	0.9000	C3—H3B	0.9600
O1—C5	1.399 (11)	C3—H3C	0.9600
O1—C1	1.415 (10)
Cl1—Bi1—Cl2	94.42 (7)	C1—C2—H2B	109.5
Cl1—Bi1—Cl4	93.03 (9)	N1—C2—H2B	109.5
Cl2—Bi1—Cl4	86.25 (6)	H2A—C2—H2B	108.1
Cl1—Bi1—Cl3i	87.74 (8)	O1—C1—C2	111.8 (7)
Cl2—Bi1—Cl3i	90.88 (6)	O1—C1—H1B	109.3
Cl4—Bi1—Cl3i	177.08 (6)	C2—C1—H1B	109.3
Cl1—Bi1—Cl4ii	92.51 (7)	O1—C1—H1C	109.3
Cl2—Bi1—Cl4ii	168.41 (7)	C2—C1—H1C	109.3
Cl4—Bi1—Cl4ii	84.11 (6)	H1B—C1—H1C	107.9
Cl3i—Bi1—Cl4ii	98.68 (6)	C5—C4—N1	110.5 (7)
Cl1—Bi1—Cl3	170.68 (7)	C5—C4—H4A	109.5
Cl2—Bi1—Cl3	85.68 (6)	N1—C4—H4A	109.5
Cl4—Bi1—Cl3	96.28 (7)	C5—C4—H4B	109.5
Cl3i—Bi1—Cl3	82.94 (6)	N1—C4—H4B	109.5
Cl4ii—Bi1—Cl3	88.98 (6)	H4A—C4—H4B	108.1
Bi1—Cl4—Bi1ii	95.89 (6)	O1—C5—C4	113.1 (7)
Bi1i—Cl3—Bi1	96.97 (6)	O1—C5—H5A	109.0
C3—N1—C4	112.6 (7)	C4—C5—H5A	109.0
C3—N1—C2	111.5 (7)	O1—C5—H5B	109.0
C4—N1—C2	108.8 (6)	C4—C5—H5B	109.0
C3—N1—H1	111.6	H5A—C5—H5B	107.8
C4—N1—H1	108.7	N1—C3—H3A	109.5
C2—N1—H1	103.1	N1—C3—H3B	109.5
C5—O1—C1	110.7 (6)	H3A—C3—H3B	109.5
C1—C2—N1	110.7 (6)	N1—C3—H3C	109.5
C1—C2—H2A	109.5	H3A—C3—H3C	109.5
N1—C2—H2A	109.5	H3B—C3—H3C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl3ii	0.90	2.76	3.434 (6)	133
N1—H1···Cl2ii	0.90	2.85	3.410 (6)	122

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl3i	0.90	2.76	3.434 (6)	133
N1—H1⋯Cl2i	0.90	2.85	3.410 (6)	122

Symmetry code: (i) .