Tris(morpholine-4-dithio­carboxyl­ato-κ2S,S′)anti­mony(III)

Zhai, J.; Yin, H.; Wang, D.

doi:10.1107/S1600536807056516

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Tris(morpholine-4-dithiocarboxylato-κ²S,S′)antimony(III)

J. Zhai, H. Yin and D. Wang

In the title compound, [Sb(C₅H₈NOS₂)₃], the Sb^III ion adopts a distorted pentagonal–pyramidal geometry because of its stereochemically active lone pair of electrons. In the crystal structure, the molecules are associated into dimers by short intermolecular Sb

S contacts [3.4111 (17) Å].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807056516/at2460sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807056516/at2460Isup2.hkl Contains datablock I

CCDC reference: 672641

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.010 Å
R factor = 0.044
wR factor = 0.111
Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.12 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C14
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         10
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C14    -   C15    ...       1.43 Ang.

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Sb1         (3)       3.30

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

Dithiocarbamates have been known as effective ligands for transition metal ions, which can form chelates (Xu et al., 2001) or act as bridging ligands (Bardaji et al., 1994). As a contribution to the chemistry of main-group metal complexes with dithiocarbamates, we present here the synthesis and crystal structure of the title compound (I).

In (I) (Fig. 1), the Sb^III ion is coordinated by the six S atoms [Sb—S 2.474 (2)–2.833 (2) Å] belonging to three morpholine-4-dithiocarboxylate ligands. The resulting SbS₆ coordination polyhedron approximates to a pentagonal pyramid with atoms Sb1 and S2—S6 at the base of the pyramid and S1 in the apical position. Three of the five equatorial Sb—S bonds are long (to S2, S3 and S5), two are short (to S4 and S6), while the apical donor atom forms the strongest bond [Sb1—S1=2.474 (2)]. The Sb^III lone pair of electrons may project in a direction roughly trans to the Sb1—S1 bond. The short intermolecular distance Sb1···S3ⁱ of 3.411 (2) Å suggests a presence of Sb···S interactions (sSymmetry code as in Fig. 2), which lead to the dimeric associations in the crystal (Fig. 2).

Related literature top

For descriptions of the versatile coordination fashions of dithiocarbamates, see: Xu et al. (2001); Bardaji et al. (1994).

Experimental top

The title compound were prepared by reaction of antimony tribromide (36.1 mg, 0.1 mmol) with the corresponding sodium dithiocarbamate (36.3 mg, 0.3 mmol), in absolute acetone. After stirring for 5 h at room temperature, the yellow paste was obtained and then filtered. Yellow crystals suitable for X-ray analysis were obtained by slow evaporation of methanol/dichloromethane (1:2 v/v) solution over a period of two weeks (yield 90%. m.p. 435 Kk).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top

	Fig. 1. The structure of the title complex, showing 30% probability displacement ellipsoids and the atom-numbering schems. H atoms have been omitted for clarity.
	Fig. 2. Crystal packing of (I), showing the Sb···S interactions as dashed lines. [Symmetry code: (i) -x,-y,-z.]

Tris(morpholine-4-dithiocarboxylato-κ²S,S')antimony(III) top

Crystal data top

[Sb(C₅H₈NOS₂)₃]	F(000) = 1224
M_r = 608.48	D_x = 1.746 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2654 reflections
a = 12.8891 (13) Å	θ = 2.5–25.3°
b = 20.009 (2) Å	µ = 1.76 mm⁻¹
c = 9.0073 (9) Å	T = 298 K
β = 94.734 (2)°	Block, yellow
V = 2315.0 (4) Å³	0.59 × 0.20 × 0.08 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	4056 independent reflections
Radiation source: fine-focus sealed tube	2716 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.064
phi and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→12
T_min = 0.424, T_max = 0.872	k = −23→22
11465 measured reflections	l = −10→10

Refinement top

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)] = 0.044	H-atom parameters constrained
wR(F²) = 0.111	w = 1/[σ²(F_o²) + (0.0475P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
4056 reflections	Δρ_max = 0.88 e Å⁻³
253 parameters	Δρ_min = −0.58 e Å⁻³
Primary atom site location: structure-invariant direct methods

Crystal data top

[Sb(C₅H₈NOS₂)₃]	V = 2315.0 (4) Å³
M_r = 608.48	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.8891 (13) Å	µ = 1.76 mm⁻¹
b = 20.009 (2) Å	T = 298 K
c = 9.0073 (9) Å	0.59 × 0.20 × 0.08 mm
β = 94.734 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4056 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2716 reflections with I > 2σ(I)
T_min = 0.424, T_max = 0.872	R_int = 0.064
11465 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	253 parameters
wR(F²) = 0.111	H-atom parameters constrained
S = 1.01	Δρ_max = 0.88 e Å⁻³
4056 reflections	Δρ_min = −0.58 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Sb1	0.15201 (3)	0.046775 (19)	0.10064 (5)	0.03166 (16)
N1	0.3477 (3)	−0.1181 (2)	−0.0361 (6)	0.0331 (12)
N2	0.0485 (4)	0.1343 (2)	−0.3489 (6)	0.0398 (14)
N3	0.3273 (4)	0.1164 (2)	0.5276 (6)	0.0485 (15)
O1	0.4047 (4)	−0.1910 (2)	−0.2841 (5)	0.0554 (13)
O2	−0.1021 (4)	0.2012 (2)	−0.5360 (6)	0.0685 (16)
O3	0.4797 (4)	0.1579 (3)	0.7463 (6)	0.0753 (17)
S1	0.32072 (12)	0.01042 (7)	0.01547 (19)	0.0345 (4)
S2	0.16824 (12)	−0.09393 (8)	0.07939 (19)	0.0388 (4)
S3	0.07604 (12)	0.02040 (7)	−0.19772 (19)	0.0352 (4)
S4	0.15521 (13)	0.15062 (7)	−0.08730 (19)	0.0391 (4)
S5	0.24492 (15)	0.01171 (8)	0.3820 (2)	0.0473 (5)
S6	0.24826 (15)	0.14712 (8)	0.2552 (2)	0.0478 (5)
C1	0.2839 (4)	−0.0739 (3)	0.0153 (6)	0.0281 (14)
C2	0.4407 (5)	−0.1006 (3)	−0.1099 (8)	0.0446 (18)
H2A	0.5011	−0.1227	−0.0608	0.054*
H2B	0.4522	−0.0527	−0.1046	0.054*
C3	0.4259 (6)	−0.1222 (4)	−0.2688 (8)	0.056 (2)
H3A	0.3687	−0.0971	−0.3186	0.067*
H3B	0.4882	−0.1118	−0.3176	0.067*
C4	0.3158 (5)	−0.2091 (3)	−0.2104 (7)	0.0483 (18)
H4A	0.3059	−0.2571	−0.2180	0.058*
H4B	0.2549	−0.1878	−0.2600	0.058*
C5	0.3251 (5)	−0.1894 (3)	−0.0484 (7)	0.0404 (17)
H5A	0.2605	−0.1992	−0.0046	0.048*
H5B	0.3804	−0.2147	0.0050	0.048*
C6	0.0875 (4)	0.1039 (3)	−0.2247 (7)	0.0310 (14)
C7	−0.0106 (5)	0.0991 (3)	−0.4706 (8)	0.0520 (19)
H7A	−0.0212	0.0530	−0.4424	0.062*
H7B	0.0281	0.0995	−0.5585	0.062*
C8	−0.1123 (6)	0.1322 (3)	−0.5040 (9)	0.061 (2)
H8A	−0.1492	0.1103	−0.5888	0.073*
H8B	−0.1536	0.1271	−0.4194	0.073*
C9	−0.0489 (5)	0.2341 (3)	−0.4159 (9)	0.060 (2)
H9A	−0.0891	0.2308	−0.3298	0.072*
H9B	−0.0425	0.2811	−0.4402	0.072*
C10	0.0562 (5)	0.2058 (3)	−0.3781 (8)	0.0462 (18)
H10A	0.0992	0.2131	−0.4600	0.055*
H10B	0.0888	0.2281	−0.2907	0.055*
C11	0.2771 (5)	0.0935 (3)	0.4024 (7)	0.0341 (15)
C12	0.3629 (6)	0.0738 (3)	0.6512 (8)	0.059 (2)
H12A	0.3596	0.0275	0.6199	0.070*
H12B	0.3180	0.0794	0.7316	0.070*
C13	0.4711 (6)	0.0911 (4)	0.7045 (9)	0.069 (2)
H13A	0.4935	0.0631	0.7890	0.083*
H13B	0.5165	0.0824	0.6261	0.083*
C14	0.4465 (7)	0.1995 (4)	0.6268 (11)	0.088 (3)
H14A	0.4951	0.1950	0.5507	0.105*
H14B	0.4501	0.2454	0.6614	0.105*
C15	0.3438 (6)	0.1874 (3)	0.5596 (8)	0.058 (2)
H15A	0.3332	0.2127	0.4677	0.070*
H15B	0.2931	0.2026	0.6260	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sb1	0.0340 (3)	0.0308 (2)	0.0303 (3)	−0.00067 (18)	0.00391 (18)	−0.00238 (19)
N1	0.026 (3)	0.033 (3)	0.042 (3)	−0.001 (2)	0.007 (2)	−0.003 (2)
N2	0.046 (3)	0.030 (3)	0.041 (4)	0.000 (2)	−0.011 (3)	0.004 (3)
N3	0.075 (4)	0.031 (3)	0.035 (4)	−0.014 (3)	−0.017 (3)	0.003 (3)
O1	0.072 (3)	0.052 (3)	0.044 (3)	0.004 (3)	0.017 (3)	−0.010 (2)
O2	0.071 (4)	0.049 (3)	0.080 (4)	−0.004 (3)	−0.030 (3)	0.017 (3)
O3	0.084 (4)	0.076 (4)	0.062 (4)	−0.025 (3)	−0.022 (3)	0.005 (3)
S1	0.0309 (9)	0.0300 (8)	0.0432 (11)	−0.0040 (7)	0.0070 (8)	0.0009 (7)
S2	0.0384 (10)	0.0340 (9)	0.0459 (12)	−0.0059 (7)	0.0146 (8)	−0.0017 (8)
S3	0.0397 (9)	0.0282 (8)	0.0366 (10)	−0.0016 (7)	−0.0041 (8)	−0.0003 (7)
S4	0.0501 (10)	0.0301 (8)	0.0351 (11)	−0.0022 (7)	−0.0086 (8)	−0.0017 (7)
S5	0.0728 (13)	0.0321 (9)	0.0356 (11)	−0.0122 (8)	−0.0032 (10)	0.0030 (8)
S6	0.0751 (13)	0.0305 (9)	0.0350 (11)	−0.0057 (8)	−0.0128 (10)	0.0035 (8)
C1	0.024 (3)	0.030 (3)	0.030 (4)	0.000 (3)	−0.001 (3)	0.003 (3)
C2	0.035 (4)	0.044 (4)	0.056 (5)	0.004 (3)	0.012 (4)	−0.009 (4)
C3	0.058 (5)	0.060 (5)	0.053 (5)	0.003 (4)	0.021 (4)	0.003 (4)
C4	0.061 (5)	0.045 (4)	0.037 (5)	−0.002 (3)	−0.010 (4)	−0.003 (3)
C5	0.051 (4)	0.026 (3)	0.045 (5)	0.007 (3)	0.008 (3)	−0.003 (3)
C6	0.026 (3)	0.036 (3)	0.031 (4)	0.008 (3)	−0.004 (3)	−0.001 (3)
C7	0.073 (5)	0.042 (4)	0.038 (5)	0.004 (4)	−0.014 (4)	−0.008 (3)
C8	0.069 (5)	0.047 (4)	0.062 (6)	−0.013 (4)	−0.028 (4)	0.012 (4)
C9	0.059 (5)	0.035 (4)	0.082 (6)	0.007 (3)	−0.009 (5)	0.012 (4)
C10	0.052 (4)	0.037 (4)	0.047 (5)	−0.009 (3)	−0.013 (4)	0.011 (3)
C11	0.045 (4)	0.032 (3)	0.026 (4)	0.000 (3)	0.005 (3)	−0.002 (3)
C12	0.086 (6)	0.045 (4)	0.042 (5)	−0.019 (4)	−0.019 (4)	0.010 (4)
C13	0.072 (6)	0.085 (7)	0.047 (6)	−0.008 (5)	−0.015 (4)	0.009 (5)
C14	0.103 (8)	0.057 (5)	0.098 (8)	−0.035 (5)	−0.020 (6)	0.002 (5)
C15	0.082 (6)	0.043 (4)	0.045 (5)	−0.010 (4)	−0.019 (4)	−0.006 (3)

Geometric parameters (Å, º) top

Sb1—S1	2.4742 (16)	C2—H2A	0.9700
Sb1—S4	2.6826 (16)	C2—H2B	0.9700
Sb1—S6	2.6876 (17)	C3—H3A	0.9700
Sb1—S5	2.8015 (18)	C3—H3B	0.9700
Sb1—S2	2.8307 (16)	C4—C5	1.507 (9)
Sb1—S3	2.8329 (17)	C4—H4A	0.9700
Sb1—S3ⁱ	3.4111 (17)	C4—H4B	0.9700
N1—C1	1.316 (7)	C5—H5A	0.9700
N1—C5	1.459 (7)	C5—H5B	0.9700
N1—C2	1.460 (7)	C7—C8	1.477 (9)
N2—C6	1.335 (7)	C7—H7A	0.9700
N2—C10	1.460 (7)	C7—H7B	0.9700
N2—C7	1.462 (7)	C8—H8A	0.9700
N3—C11	1.334 (7)	C8—H8B	0.9700
N3—C12	1.446 (8)	C9—C10	1.482 (8)
N3—C15	1.461 (8)	C9—H9A	0.9700
O1—C3	1.409 (8)	C9—H9B	0.9700
O1—C4	1.418 (8)	C10—H10A	0.9700
O2—C9	1.397 (8)	C10—H10B	0.9700
O2—C8	1.419 (7)	C12—C13	1.478 (9)
O3—C13	1.390 (9)	C12—H12A	0.9700
O3—C14	1.399 (9)	C12—H12B	0.9700
S1—C1	1.753 (6)	C13—H13A	0.9700
S2—C1	1.691 (6)	C13—H13B	0.9700
S3—C6	1.696 (6)	C14—C15	1.431 (9)
S4—C6	1.729 (6)	C14—H14A	0.9700
S5—C11	1.695 (6)	C14—H14B	0.9700
S6—C11	1.722 (6)	C15—H15A	0.9700
C2—C3	1.492 (9)	C15—H15B	0.9700

S1—Sb1—S4	88.42 (5)	N1—C5—C4	109.3 (5)
S1—Sb1—S6	90.02 (6)	N1—C5—H5A	109.8
S4—Sb1—S6	73.60 (5)	C4—C5—H5A	109.8
S1—Sb1—S5	83.44 (6)	N1—C5—H5B	109.8
S4—Sb1—S5	137.49 (5)	C4—C5—H5B	109.8
S6—Sb1—S5	64.78 (5)	H5A—C5—H5B	108.3
S1—Sb1—S2	67.35 (5)	N2—C6—S3	122.5 (4)
S4—Sb1—S2	136.27 (5)	N2—C6—S4	119.1 (4)
S6—Sb1—S2	138.11 (5)	S3—C6—S4	118.4 (3)
S5—Sb1—S2	77.50 (5)	N2—C7—C8	109.7 (6)
S1—Sb1—S3	83.97 (5)	N2—C7—H7A	109.7
S4—Sb1—S3	64.39 (5)	C8—C7—H7A	109.7
S6—Sb1—S3	137.66 (5)	N2—C7—H7B	109.7
S5—Sb1—S3	154.16 (5)	C8—C7—H7B	109.7
S2—Sb1—S3	76.84 (5)	H7A—C7—H7B	108.2
S1—Sb1—S3ⁱ	139.61 (4)	O2—C8—C7	112.4 (6)
S4—Sb1—S3ⁱ	121.70 (5)	O2—C8—H8A	109.1
S6—Sb1—S3ⁱ	122.16 (5)	C7—C8—H8A	109.1
S5—Sb1—S3ⁱ	88.99 (5)	O2—C8—H8B	109.1
S2—Sb1—S3ⁱ	72.27 (4)	C7—C8—H8B	109.1
S3—Sb1—S3ⁱ	86.11 (5)	H8A—C8—H8B	107.9
C1—N1—C5	123.8 (5)	O2—C9—C10	112.3 (6)
C1—N1—C2	124.0 (5)	O2—C9—H9A	109.2
C5—N1—C2	111.4 (5)	C10—C9—H9A	109.2
C6—N2—C10	124.8 (5)	O2—C9—H9B	109.2
C6—N2—C7	123.1 (5)	C10—C9—H9B	109.2
C10—N2—C7	112.0 (5)	H9A—C9—H9B	107.9
C11—N3—C12	123.4 (5)	N2—C10—C9	110.0 (5)
C11—N3—C15	123.5 (5)	N2—C10—H10A	109.7
C12—N3—C15	112.9 (5)	C9—C10—H10A	109.7
C3—O1—C4	111.2 (5)	N2—C10—H10B	109.7
C9—O2—C8	110.4 (5)	C9—C10—H10B	109.7
C13—O3—C14	110.6 (6)	H10A—C10—H10B	108.2
C1—S1—Sb1	92.21 (19)	N3—C11—S5	121.3 (5)
C1—S2—Sb1	81.9 (2)	N3—C11—S6	119.7 (4)
C6—S3—Sb1	85.7 (2)	S5—C11—S6	118.9 (4)
C6—S4—Sb1	90.0 (2)	N3—C12—C13	110.1 (6)
C11—S5—Sb1	86.5 (2)	N3—C12—H12A	109.6
C11—S6—Sb1	89.7 (2)	C13—C12—H12A	109.6
N1—C1—S2	123.7 (4)	N3—C12—H12B	109.6
N1—C1—S1	118.0 (4)	C13—C12—H12B	109.6
S2—C1—S1	118.3 (3)	H12A—C12—H12B	108.2
N1—C2—C3	108.8 (5)	O3—C13—C12	111.4 (7)
N1—C2—H2A	109.9	O3—C13—H13A	109.3
C3—C2—H2A	109.9	C12—C13—H13A	109.3
N1—C2—H2B	109.9	O3—C13—H13B	109.3
C3—C2—H2B	109.9	C12—C13—H13B	109.3
H2A—C2—H2B	108.3	H13A—C13—H13B	108.0
O1—C3—C2	112.7 (6)	O3—C14—C15	116.0 (7)
O1—C3—H3A	109.1	O3—C14—H14A	108.3
C2—C3—H3A	109.1	C15—C14—H14A	108.3
O1—C3—H3B	109.1	O3—C14—H14B	108.3
C2—C3—H3B	109.1	C15—C14—H14B	108.3
H3A—C3—H3B	107.8	H14A—C14—H14B	107.4
O1—C4—C5	112.6 (5)	C14—C15—N3	111.2 (6)
O1—C4—H4A	109.1	C14—C15—H15A	109.4
C5—C4—H4A	109.1	N3—C15—H15A	109.4
O1—C4—H4B	109.1	C14—C15—H15B	109.4
C5—C4—H4B	109.1	N3—C15—H15B	109.4
H4A—C4—H4B	107.8	H15A—C15—H15B	108.0

Symmetry code: (i) −x, −y, −z.

Experimental details

Crystal data
Chemical formula	[Sb(C₅H₈NOS₂)₃]
M_r	608.48
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	12.8891 (13), 20.009 (2), 9.0073 (9)
β (°)	94.734 (2)
V (Å³)	2315.0 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.76
Crystal size (mm)	0.59 × 0.20 × 0.08

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.424, 0.872
No. of measured, independent and observed [I > 2σ(I)] reflections	11465, 4056, 2716
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.111, 1.01
No. of reflections	4056
No. of parameters	253
No. of restraints	?
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.88, −0.58

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Selected geometric parameters (Å, º) top

Sb1—S1	2.4742 (16)	Sb1—S2	2.8307 (16)
Sb1—S4	2.6826 (16)	Sb1—S3	2.8329 (17)
Sb1—S6	2.6876 (17)	Sb1—S3ⁱ	3.4111 (17)
Sb1—S5	2.8015 (18)

S1—Sb1—S4	88.42 (5)	S6—Sb1—S2	138.11 (5)
S1—Sb1—S6	90.02 (6)	S5—Sb1—S2	77.50 (5)
S4—Sb1—S6	73.60 (5)	S1—Sb1—S3	83.97 (5)
S1—Sb1—S5	83.44 (6)	S4—Sb1—S3	64.39 (5)
S4—Sb1—S5	137.49 (5)	S6—Sb1—S3	137.66 (5)
S6—Sb1—S5	64.78 (5)	S5—Sb1—S3	154.16 (5)
S1—Sb1—S2	67.35 (5)	S2—Sb1—S3	76.84 (5)
S4—Sb1—S2	136.27 (5)

Symmetry code: (i) −x, −y, −z.

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