Dimorpholinium penta-chloridoanti-monate(III).

The asymmetric unit of the title compound, (C(4)H(10)NO)(2)[SbCl(5)], consists of two morpholinium cations in chair conformations, and a penta-chloridoanti-monate dianion with the Sb(III) ion in a slightly distorted square-pyramidal coordination environment. The morpholinium cations are connected to each other by N-H⋯O hydrogen bonds, and they link the chloride anions and the anti-monate SbCl(3) group via N-H⋯Cl contacts.

Related literature

For a phase transition in bis­(ethyl­dimethyl­ammonium) penta­chlorido­anti­monate(III), see: Bujak & Zaleski (1999 ▶); for the structure of N-methyl­piperazinediium penta­chlorido­­anti­monate(III), see: Shen-Tu et al. (2008 ▶); for the low-temperature phase of morpholinium tetra­fluorido­borate, see: Owczarek et al. (2008 ▶).

Experimental

Crystal data

(C4H10NO)2[SbCl5]

M = 475.26

Orthorhombic,

a = 9.0562 (18) Å

b = 10.273 (2) Å

c = 18.032 (4) Å

V = 1677.6 (6) Å3

Z = 4

Mo Kα radiation

μ = 2.44 mm−1

T = 298 K

0.25 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury2 (2× 2 bin mode) diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.567, T max = 0.616

17552 measured reflections

3845 independent reflections

3759 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.046

S = 1.24

3845 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.66 e Å−3

Absolute structure: Flack (1983 ▶)

Flack parameter: −0.005 (15)

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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809019345/si2174sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019345/si2174Isup2.hkl

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

(C4H10NO)2[SbCl5]	F(000) = 936
Mr = 475.26	Dx = 1.882 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3845 reflections
a = 9.0562 (18) Å	θ = 3–27.5°
b = 10.273 (2) Å	µ = 2.44 mm−1
c = 18.032 (4) Å	T = 298 K
V = 1677.6 (6) Å3	Block, colourless
Z = 4	0.25 × 0.20 × 0.20 mm

Rigaku Mercury2 (2× 2 bin mode) diffractometer	3845 independent reflections
Radiation source: fine-focus sealed tube	3759 reflections with I > 2σ(I)
graphite	Rint = 0.026
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.0°
ω scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −13→13
Tmin = 0.567, Tmax = 0.616	l = −23→23
17552 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)] = 0.021	H-atom parameters constrained
wR(F2) = 0.046	w = 1/[σ2(Fo2) + (0.0201P)2] where P = (Fo2 + 2Fc2)/3
S = 1.24	(Δ/σ)max = 0.003
3845 reflections	Δρmax = 0.32 e Å−3
163 parameters	Δρmin = −0.66 e Å−3
0 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.005 (15)

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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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	0.7135 (3)	0.5818 (4)	0.95313 (17)	0.0425 (8)
H1A	0.7413	0.6730	0.9546	0.051*
H1B	0.7866	0.5329	0.9808	0.051*
C2	0.5653 (4)	0.5651 (3)	0.98887 (17)	0.0431 (7)
H2A	0.5395	0.4735	0.9906	0.052*
H2B	0.5680	0.5980	1.0393	0.052*
C3	0.4560 (3)	0.5973 (4)	0.86593 (18)	0.0459 (8)
H3A	0.3890	0.6514	0.8374	0.055*
H3B	0.4236	0.5076	0.8616	0.055*
C4	0.6092 (3)	0.6104 (3)	0.83609 (17)	0.0440 (8)
H4A	0.6114	0.5797	0.7852	0.053*
H4B	0.6372	0.7016	0.8361	0.053*
C5	0.8890 (4)	0.6967 (3)	0.68509 (19)	0.0461 (8)
H5A	0.7903	0.6605	0.6819	0.055*
H5B	0.9521	0.6478	0.6516	0.055*
C6	0.8854 (3)	0.8366 (3)	0.66122 (19)	0.0442 (8)
H6A	0.8495	0.8431	0.6107	0.053*
H6B	0.8196	0.8858	0.6931	0.053*
C7	1.0960 (3)	0.8730 (3)	0.74228 (15)	0.0376 (6)
H7A	1.0382	0.9243	0.7769	0.045*
H7B	1.1976	0.9028	0.7446	0.045*
C8	1.0880 (4)	0.7312 (3)	0.76295 (16)	0.0411 (7)
H8A	1.1510	0.6814	0.7299	0.049*
H8B	1.1247	0.7199	0.8131	0.049*
Cl1	0.82449 (9)	1.24256 (9)	0.98134 (4)	0.0472 (2)
Cl2	0.55039 (9)	1.24280 (7)	0.82480 (4)	0.04292 (19)
Cl3	0.39146 (8)	0.94495 (7)	0.87224 (4)	0.03967 (18)
Cl4	0.76734 (9)	0.96688 (8)	0.86621 (5)	0.04330 (19)
Cl5	0.60479 (7)	0.89292 (7)	1.04341 (4)	0.03298 (15)
N1	0.4534 (2)	0.6378 (2)	0.94513 (14)	0.0407 (6)
H1C	0.4718	0.7238	0.9483	0.049*
H1D	0.3631	0.6231	0.9641	0.049*
N2	1.0376 (3)	0.8903 (2)	0.66613 (14)	0.0365 (6)
H2C	1.0966	0.8490	0.6336	0.044*
H2D	1.0366	0.9754	0.6544	0.044*
O1	0.7123 (2)	0.5387 (2)	0.87871 (12)	0.0377 (5)
O2	0.9422 (2)	0.6830 (2)	0.75855 (11)	0.0430 (5)
Sb1	0.580748 (19)	1.092473 (15)	0.928491 (9)	0.02418 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0334 (15)	0.054 (2)	0.0404 (17)	0.0040 (17)	−0.0037 (13)	−0.0141 (16)
C2	0.0470 (18)	0.0450 (18)	0.0374 (16)	−0.0036 (16)	0.0051 (15)	−0.0036 (13)
C3	0.0338 (16)	0.053 (2)	0.0507 (19)	0.0112 (17)	−0.0098 (13)	−0.0112 (17)
C4	0.0459 (18)	0.0497 (19)	0.0364 (16)	0.0138 (17)	0.0012 (13)	0.0029 (14)
C5	0.0397 (18)	0.0457 (18)	0.0531 (19)	−0.0173 (15)	−0.0041 (15)	0.0022 (15)
C6	0.0322 (16)	0.0501 (19)	0.0502 (19)	−0.0012 (15)	−0.0070 (14)	0.0157 (15)
C7	0.0376 (15)	0.0393 (15)	0.0360 (15)	−0.0078 (14)	0.0006 (13)	−0.0015 (12)
C8	0.0445 (17)	0.0466 (17)	0.0322 (15)	0.0030 (17)	−0.0056 (15)	0.0060 (12)
Cl1	0.0464 (4)	0.0481 (5)	0.0472 (5)	−0.0051 (4)	0.0000 (4)	−0.0024 (4)
Cl2	0.0547 (5)	0.0364 (4)	0.0377 (4)	−0.0036 (4)	−0.0052 (3)	0.0098 (3)
Cl3	0.0387 (4)	0.0398 (4)	0.0405 (4)	−0.0074 (3)	−0.0098 (3)	0.0001 (3)
Cl4	0.0394 (4)	0.0377 (4)	0.0529 (5)	0.0030 (4)	0.0191 (4)	−0.0080 (3)
Cl5	0.0284 (3)	0.0367 (4)	0.0338 (3)	0.0025 (3)	0.0000 (3)	0.0024 (3)
N1	0.0215 (11)	0.0392 (14)	0.0613 (18)	−0.0020 (10)	0.0108 (11)	−0.0130 (12)
N2	0.0381 (13)	0.0300 (13)	0.0413 (14)	−0.0037 (11)	0.0054 (10)	0.0085 (11)
O1	0.0298 (11)	0.0443 (13)	0.0389 (12)	0.0123 (9)	0.0013 (9)	−0.0074 (10)
O2	0.0443 (12)	0.0420 (11)	0.0427 (12)	−0.0127 (11)	0.0039 (10)	0.0146 (9)
Sb1	0.02303 (8)	0.02452 (8)	0.02498 (8)	−0.00036 (8)	0.00101 (7)	−0.00180 (7)

C1—O1	1.413 (4)	C6—N2	1.487 (4)
C1—C2	1.499 (4)	C6—H6A	0.9700
C1—H1A	0.9700	C6—H6B	0.9700
C1—H1B	0.9700	C7—N2	1.482 (4)
C2—N1	1.485 (4)	C7—C8	1.506 (4)
C2—H2A	0.9700	C7—H7A	0.9700
C2—H2B	0.9700	C7—H7B	0.9700
C3—N1	1.488 (4)	C8—O2	1.412 (4)
C3—C4	1.494 (4)	C8—H8A	0.9700
C3—H3A	0.9700	C8—H8B	0.9700
C3—H3B	0.9700	Cl1—Sb1	2.8562 (9)
C4—O1	1.416 (4)	Cl2—Sb1	2.4405 (8)
C4—H4A	0.9700	Cl3—Sb1	2.5028 (8)
C4—H4B	0.9700	Cl4—Sb1	2.4045 (8)
C5—O2	1.417 (4)	N1—H1C	0.9000
C5—C6	1.501 (4)	N1—H1D	0.9000
C5—H5A	0.9700	N2—H2C	0.9000
C5—H5B	0.9700	N2—H2D	0.9000
O1—C1—C2	111.4 (2)	C5—C6—H6B	110.0
O1—C1—H1A	109.3	H6A—C6—H6B	108.4
C2—C1—H1A	109.3	N2—C7—C8	109.1 (2)
O1—C1—H1B	109.3	N2—C7—H7A	109.9
C2—C1—H1B	109.3	C8—C7—H7A	109.9
H1A—C1—H1B	108.0	N2—C7—H7B	109.9
N1—C2—C1	109.0 (3)	C8—C7—H7B	109.9
N1—C2—H2A	109.9	H7A—C7—H7B	108.3
C1—C2—H2A	109.9	O2—C8—C7	111.7 (3)
N1—C2—H2B	109.9	O2—C8—H8A	109.3
C1—C2—H2B	109.9	C7—C8—H8A	109.3
H2A—C2—H2B	108.3	O2—C8—H8B	109.3
N1—C3—C4	109.6 (2)	C7—C8—H8B	109.3
N1—C3—H3A	109.8	H8A—C8—H8B	107.9
C4—C3—H3A	109.8	C2—N1—C3	111.0 (2)
N1—C3—H3B	109.8	C2—N1—H1C	109.4
C4—C3—H3B	109.8	C3—N1—H1C	109.4
H3A—C3—H3B	108.2	C2—N1—H1D	109.4
O1—C4—C3	111.7 (3)	C3—N1—H1D	109.4
O1—C4—H4A	109.3	H1C—N1—H1D	108.0
C3—C4—H4A	109.3	C7—N2—C6	110.0 (2)
O1—C4—H4B	109.3	C7—N2—H2C	109.7
C3—C4—H4B	109.3	C6—N2—H2C	109.7
H4A—C4—H4B	107.9	C7—N2—H2D	109.7
O2—C5—C6	111.7 (3)	C6—N2—H2D	109.7
O2—C5—H5A	109.3	H2C—N2—H2D	108.2
C6—C5—H5A	109.3	C1—O1—C4	111.0 (2)
O2—C5—H5B	109.3	C8—O2—C5	109.6 (2)
C6—C5—H5B	109.3	Cl4—Sb1—Cl2	93.49 (3)
H5A—C5—H5B	107.9	Cl4—Sb1—Cl3	88.12 (3)
N2—C6—C5	108.5 (2)	Cl2—Sb1—Cl3	89.74 (3)
N2—C6—H6A	110.0	Cl4—Sb1—Cl1	84.40 (3)
C5—C6—H6A	110.0	Cl2—Sb1—Cl1	90.06 (3)
N2—C6—H6B	110.0	Cl3—Sb1—Cl1	172.49 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···Cl5i	0.90	2.35	3.180 (2)	154
C1—H1B···Cl3ii	0.97	2.82	3.548 (3)	132
N2—H2D···Cl5iii	0.90	2.73	3.394 (2)	131
N2—H2C···Cl1iv	0.90	2.45	3.306 (3)	159
N2—H2D···O1v	0.90	2.44	2.848 (3)	108
N1—H1C···Cl3	0.90	2.75	3.463 (3)	137
N1—H1C···Cl5	0.90	2.72	3.448 (3)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1D⋯Cl5i	0.90	2.35	3.180 (2)	154
C1—H1B⋯Cl3ii	0.97	2.82	3.548 (3)	132
N2—H2D⋯Cl5iii	0.90	2.73	3.394 (2)	131
N2—H2C⋯Cl1iv	0.90	2.45	3.306 (3)	159
N2—H2D⋯O1v	0.90	2.44	2.848 (3)	108
N1—H1C⋯Cl3	0.90	2.75	3.463 (3)	137
N1—H1C⋯Cl5	0.90	2.72	3.448 (3)	138

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .