Crystal structure of di­chlorido­[2-(di­phenyl­phosphan­yl)-3,4,5,6-tetra­fluoro­benzene-1-thiol­ato-κ2P,S]gold(III)

Corfield, P.W.R.; Bailey, M.

doi:10.1107/S2056989015016758

metal-organic compounds

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Volume 71| Part 10| October 2015| Pages m181-m182

doi:10.1107/S2056989015016758

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Crystal structure of dichlorido[2-(diphenylphosphanyl)-3,4,5,6-tetrafluorobenzene-1-thiolato-κ²P,S]gold(III)

Peter W. R. Corfield ^a ^* and Mary Bailey ^b

^aDepartment of Chemistry, Fordham University, 441 East Fordham Road, Bronx, NY 10458, USA, and ^bDepartment of Chemistry, The Ohio State University, Columbus, Ohio 43210, USA
^*Correspondence e-mail: pcorfield@fordham.edu

Edited by M. Weil, Vienna University of Technology, Austria (Received 25 August 2015; accepted 7 September 2015; online 17 September 2015)

The title compound, [Au(C₁₈H₁₀F₄PS)Cl₂], crystallizes as neutral molecules, with the Au^III atom coordinated by two Cl atoms and by the P and S atoms of the bidentate phosphanyl thiolate ligand, in a slightly distorted square-planar environment. The molecules are linked into centrosymmetric dimers via long axial Au—Cl bonds of 3.393 (4) Å. This axial Au—Cl distance is longer than is usually seen, although one other example has been given. Dimer formation may explain the unexpectedly low solubility of the compound in common polar solvents. There is also a separate intermolecular Au—F contact of 3.561 (6) Å, but this distance seems too long to be regarded as a bond. Two putative C—H⋯F hydrogen bonds appear to link the dimers into sheets parallel to (110). There is a short intermolecular F⋯F contact of 2.695 (10) Å between two dimers related by the twofold axis.

Keywords: crystal structure; mixed ligand; gold complex.

CCDC reference: 1422931

1. Related literature

For synthetic details, see: Eller (1971 ); Eller & Meek (1970 ). Hollis & Lippard (1983 ) describe a similarly long axial Au—Cl bond in a mixed-valence gold compound, although other axial Au—Cl bonds in the literature are in the 3.0–3.1 Å range, as in Elder & Watkins (1986 ).

2. Experimental

2.1. Crystal data

[Au(C₁₈H₁₀F₄PS)Cl₂]
M_r = 633.16
Monoclinic, C 2/c
a = 18.90 (2) Å
b = 8.388 (12) Å
c = 24.15 (3) Å
β = 100.75 (3)°
V = 3761 (8) Å³
Z = 8
Mo Kα radiation
μ = 8.15 mm⁻¹
T = 298 K
0.22 × 0.16 × 0.13 mm

2.2. Data collection

Picker 4-circle diffractometer
Absorption correction: gaussian (Busing & Levy, 1957 ) T_min = 0.384, T_max = 0.442
4262 measured reflections
4142 independent reflections
3209 reflections with I > 2σ(I)
R_int = 0.025
18 standard reflections every 500 reflections intensity decay: −1.0(3)

2.3. Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.086
S = 1.03
4142 reflections
220 parameters
H-atom parameters constrained
Δρ_max = 1.00 e Å⁻³
Δρ_min = −0.87 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Au—S	2.273 (3)
Au—P	2.258 (3)
Au—Cl2	2.337 (3)
Au—Cl1	2.305 (3)

S—Au—P	90.22 (10)
S—Au—Cl2	87.51 (10)
P—Au—Cl2	177.69 (6)
S—Au—Cl1	176.59 (7)
P—Au—Cl1	88.36 (10)
Cl2—Au—Cl1	93.88 (11)
S—Au—Cl2ⁱ	88.12 (7)
P—Au—Cl2ⁱ	90.45 (9)
Cl2—Au—Cl2ⁱ	89.91 (9)
Cl1—Au—Cl2ⁱ	94.99 (7)
Symmetry code: (i) -x, -y, -z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯F3ⁱⁱ	0.93	2.60	3.444 (7)	151
C18—H18⋯F4ⁱⁱⁱ	0.93	2.50	3.082 (7)	121
Symmetry codes: (ii) x, y-1, z; (iii) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: Corfield (1972 ); cell refinement: Corfield (1972); data reduction: Corfield et al. (1973 ); program(s) used to solve structure: Corfield (1972); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ); software used to prepare material for publication: SHELXL2014.

Supporting information

CCDC reference: 1422931

Crystal structure: contains datablock I. DOI: 10.1107/S2056989015016758/wm5209sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015016758/wm5209Isup2.hkl

checkCIF report

Synthesis and crystallization top

The preparation of the compound is described by Eller (1971), and synthesis of the then novel ligand is given in Eller & Meek (1970).

Refinement top

To reduce the number of parameters varied, the phenyl groups C16—C21 and C22—C27 were constrained as rigid hexagons, with C—C distances of 1.385 Å. Aromatic H atoms were placed geometrically, with their U_eq values set 1.2 times the U_iso of their bonded C atoms.

Related literature top

For synthetic details, see: Eller (1971); Eller & Meek (1970). Hollis & Lippard (1983) describe a similarly long axial Au—Cl bond in a mixed-valence gold compound, although other axial Au—Cl bonds in the literature are in the 3.0–3.1 Å range, as in Elder & Watkins (1986).

Computing details top

Data collection: Corfield (1972); cell refinement: Corfield (1972); data reduction: Corfield et al. (1973); program(s) used to solve structure: Corfield (1972); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Packing of the title complex, viewed along a direction near to the a axis. The centrosymmetric dimers are shown, as well as the proximity of F3(1,y - 1,z) to a sixth coordination site for the gold atom. Long Au—Cl bonds are gived as dashed lines.

Dichlorido[2-(diphenylphosphanyl)-3,4,5,6-tetrafluorobenzene-1-thiolato-κ²P,S]gold(III) top

Crystal data top

[Au(C₁₈H₁₀F₄PS)Cl₂]	F(000) = 2384
M_r = 633.16	D_x = 2.236 Mg m⁻³ D_m = 2.181 (3) Mg m⁻³ D_m measured by flotation in carbon tetrachloride/bromoforom mixture. Discrepancy may be due to an uncalibrated pycnometer.
Monoclinic, C2/c	Mo Kα radiation, λ = 0.7107 Å
a = 18.90 (2) Å	Cell parameters from 24 reflections
b = 8.388 (12) Å	θ = 4.2–25.1°
c = 24.15 (3) Å	µ = 8.15 mm⁻¹
β = 100.75 (3)°	T = 298 K
V = 3761 (8) Å³	Irregular, red
Z = 8	0.22 × 0.16 × 0.13 mm

Data collection top

Picker 4-circle diffractometer	3209 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube	R_int = 0.025
Oriented graphite 200 reflection monochromator	θ_max = 27.5°, θ_min = 2.5°
θ/2θ scans	h = 0→24
Absorption correction: gaussian (Busing & Levy, 1957)	k = 0→9
T_min = 0.384, T_max = 0.442	l = −31→30
4262 measured reflections	18 standard reflections every 500 reflections
4142 independent reflections	intensity decay: −1.0 (3)

Refinement top

Refinement on F²	Primary atom site location: heavy-atom method
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²)] where P = (F_o² + 2F_c²)/3
4142 reflections	(Δ/σ)_max < 0.001
220 parameters	Δρ_max = 1.00 e Å⁻³
0 restraints	Δρ_min = −0.87 e Å⁻³

Crystal data top

[Au(C₁₈H₁₀F₄PS)Cl₂]	V = 3761 (8) Å³
M_r = 633.16	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 18.90 (2) Å	µ = 8.15 mm⁻¹
b = 8.388 (12) Å	T = 298 K
c = 24.15 (3) Å	0.22 × 0.16 × 0.13 mm
β = 100.75 (3)°

Data collection top

Picker 4-circle diffractometer	3209 reflections with I > 2σ(I)
Absorption correction: gaussian (Busing & Levy, 1957)	R_int = 0.025
T_min = 0.384, T_max = 0.442	18 standard reflections every 500 reflections
4262 measured reflections	intensity decay: −1.0 (3)
4142 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.086	H-atom parameters constrained
S = 1.02	Δρ_max = 1.00 e Å⁻³
4142 reflections	Δρ_min = −0.87 e Å⁻³
220 parameters

Special details top

Experimental. Data reduction followed procedures in Corfield et al. (1973), with programs written by Corfield and by Graeme Gainsford.

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. To reduce the number of parameters varied, the phenyl groups C16—C21 and C22—C27 were constrained as rigid hexagons, with C—C distances of 1.385 Å. U_eq values for the aromatic H atoms were set 1.2 times the U_iso of their bonded C atoms.

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

	x	y	z	U_iso*/U_eq
Au	0.03240 (2)	0.02779 (3)	0.08580 (2)	0.03238 (9)
Cl1	0.14260 (10)	−0.0955 (2)	0.09200 (9)	0.0544 (5)
Cl2	−0.03221 (10)	−0.1909 (2)	0.04280 (8)	0.0503 (4)
S	−0.07524 (9)	0.1492 (2)	0.08537 (8)	0.0438 (4)
P	0.09063 (8)	0.2433 (2)	0.12802 (7)	0.0309 (3)
F2	0.1031 (2)	0.5694 (5)	0.1812 (2)	0.0572 (12)
F3	−0.0040 (3)	0.7682 (6)	0.1937 (2)	0.0681 (13)
F4	−0.1413 (3)	0.6750 (6)	0.1616 (2)	0.0757 (15)
F5	−0.1734 (2)	0.3959 (6)	0.1090 (2)	0.0622 (12)
C1	0.0205 (3)	0.3780 (8)	0.1371 (3)	0.0343 (14)
C2	0.0351 (4)	0.5243 (9)	0.1633 (3)	0.0431 (16)
C3	−0.0190 (4)	0.6241 (9)	0.1708 (3)	0.0479 (18)
C4	−0.0886 (4)	0.5795 (9)	0.1527 (3)	0.0488 (18)
C5	−0.1042 (3)	0.4341 (10)	0.1269 (3)	0.0461 (18)
C6	−0.0507 (3)	0.3312 (8)	0.1186 (3)	0.0363 (14)
C7	0.1393 (2)	0.1964 (5)	0.19702 (13)	0.0336 (14)
C8	0.2018 (2)	0.2774 (5)	0.21989 (18)	0.0490 (18)
H8	0.2215	0.3507	0.1981	0.059*
C9	0.2350 (2)	0.2494 (6)	0.27517 (19)	0.058 (2)
H9	0.2769	0.3038	0.2905	0.070*
C10	0.2057 (3)	0.1403 (6)	0.30757 (14)	0.055 (2)
H10	0.2279	0.1215	0.3447	0.066*
C11	0.1432 (3)	0.0592 (6)	0.28470 (17)	0.060 (2)
H11	0.1235	−0.0140	0.3065	0.072*
C12	0.1100 (2)	0.0873 (5)	0.22942 (18)	0.0462 (17)
H12	0.0681	0.0329	0.2141	0.055*
C13	0.1473 (2)	0.3410 (5)	0.08744 (17)	0.0352 (14)
C14	0.12320 (19)	0.4760 (5)	0.05659 (18)	0.0400 (15)
H14	0.0771	0.5146	0.0566	0.048*
C15	0.1678 (3)	0.5534 (4)	0.02581 (18)	0.0487 (18)
H15	0.1516	0.6441	0.0051	0.058*
C16	0.2365 (2)	0.4959 (6)	0.0259 (2)	0.051 (2)
H16	0.2664	0.5480	0.0052	0.062*
C17	0.26061 (18)	0.3610 (6)	0.0567 (2)	0.0527 (19)
H17	0.3068	0.3224	0.0568	0.063*
C18	0.2160 (2)	0.2835 (5)	0.08750 (19)	0.0433 (16)
H18	0.2323	0.1929	0.1082	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Au	0.03286 (13)	0.03025 (15)	0.03249 (12)	−0.00327 (11)	0.00210 (8)	−0.00023 (11)
Cl1	0.0446 (10)	0.0441 (11)	0.0717 (13)	0.0115 (8)	0.0038 (9)	−0.0094 (9)
Cl2	0.0572 (11)	0.0408 (10)	0.0499 (10)	−0.0166 (8)	0.0022 (8)	−0.0058 (8)
S	0.0279 (8)	0.0472 (11)	0.0541 (10)	−0.0065 (7)	0.0017 (7)	−0.0028 (8)
P	0.0258 (7)	0.0295 (9)	0.0361 (8)	−0.0005 (6)	0.0022 (6)	0.0001 (6)
F2	0.048 (2)	0.046 (3)	0.074 (3)	−0.006 (2)	0.000 (2)	−0.019 (2)
F3	0.082 (3)	0.051 (3)	0.071 (3)	0.010 (3)	0.012 (3)	−0.023 (2)
F4	0.066 (3)	0.073 (4)	0.088 (4)	0.037 (3)	0.015 (3)	−0.013 (3)
F5	0.034 (2)	0.072 (3)	0.080 (3)	0.009 (2)	0.008 (2)	0.005 (3)
C1	0.030 (3)	0.031 (4)	0.041 (3)	0.004 (3)	0.005 (3)	0.001 (3)
C2	0.047 (4)	0.038 (4)	0.043 (4)	0.005 (3)	0.004 (3)	−0.008 (3)
C3	0.060 (5)	0.034 (4)	0.049 (4)	0.013 (3)	0.007 (4)	−0.003 (3)
C4	0.051 (4)	0.045 (5)	0.052 (4)	0.021 (4)	0.015 (3)	0.002 (3)
C5	0.025 (3)	0.065 (5)	0.048 (4)	0.010 (3)	0.005 (3)	0.013 (4)
C6	0.036 (3)	0.041 (4)	0.032 (3)	0.003 (3)	0.005 (3)	0.007 (3)
C7	0.037 (3)	0.031 (4)	0.031 (3)	0.004 (3)	0.001 (3)	0.001 (3)
C8	0.047 (4)	0.048 (5)	0.046 (4)	−0.011 (3)	−0.006 (3)	0.006 (3)
C9	0.050 (4)	0.065 (6)	0.051 (4)	−0.001 (4)	−0.012 (4)	−0.011 (4)
C10	0.068 (5)	0.054 (5)	0.040 (4)	0.016 (4)	0.001 (4)	−0.002 (4)
C11	0.089 (6)	0.053 (5)	0.039 (4)	−0.003 (5)	0.014 (4)	0.012 (3)
C12	0.054 (4)	0.040 (4)	0.044 (4)	−0.008 (3)	0.008 (3)	0.000 (3)
C13	0.031 (3)	0.036 (4)	0.038 (3)	0.000 (3)	0.003 (3)	0.000 (3)
C14	0.042 (4)	0.039 (4)	0.040 (3)	−0.001 (3)	0.009 (3)	0.002 (3)
C15	0.070 (5)	0.031 (4)	0.047 (4)	−0.007 (4)	0.017 (4)	0.004 (3)
C16	0.059 (5)	0.051 (5)	0.047 (4)	−0.017 (4)	0.017 (4)	−0.003 (3)
C17	0.041 (4)	0.062 (5)	0.057 (5)	−0.006 (4)	0.016 (3)	−0.002 (4)
C18	0.034 (3)	0.045 (4)	0.051 (4)	0.001 (3)	0.006 (3)	−0.001 (3)

Geometric parameters (Å, º) top

Au—S	2.273 (3)	C7—C12	1.3850
Au—P	2.258 (3)	C8—C9	1.3850
Au—Cl2	2.337 (3)	C8—H8	0.9300
Au—Cl1	2.305 (3)	C9—C10	1.3850
Au—Cl2ⁱ	3.393 (4)	C9—H9	0.9300
Au—F3ⁱⁱ	3.560 (6)	C10—C11	1.3850
S—C6	1.747 (7)	C10—H10	0.9300
P—C1	1.787 (6)	C11—C12	1.3850
P—C7	1.791 (4)	C11—H11	0.9300
P—C13	1.781 (4)	C12—H12	0.9300
F2—C2	1.331 (8)	C13—C14	1.3850
F3—C3	1.337 (9)	C13—C18	1.3850
F4—C4	1.328 (8)	C14—C15	1.3850
F5—C5	1.338 (8)	C14—H14	0.9300
C1—C6	1.393 (8)	C15—C16	1.3850
C1—C2	1.385 (10)	C15—H15	0.9300
C2—C3	1.360 (10)	C16—C17	1.3850
C3—C4	1.358 (10)	C16—H16	0.9300
C4—C5	1.375 (11)	C17—C18	1.3850
C5—C6	1.372 (9)	C17—H17	0.9300
C7—C8	1.3850	C18—H18	0.9300

S—Au—P	90.22 (10)	C5—C6—S	118.5 (5)
S—Au—Cl2	87.51 (10)	C1—C6—S	123.4 (5)
P—Au—Cl2	177.69 (6)	C8—C7—C12	120.0
S—Au—Cl1	176.59 (7)	C8—C7—P	121.0 (3)
P—Au—Cl1	88.36 (10)	C12—C7—P	118.7 (3)
Cl2—Au—Cl1	93.88 (11)	C7—C8—C9	120.0
S—Au—Cl2ⁱ	88.12 (7)	C7—C8—H8	120.0
P—Au—Cl2ⁱ	90.45 (9)	C9—C8—H8	120.0
Cl2—Au—Cl2ⁱ	89.91 (9)	C10—C9—C8	120.0
Cl1—Au—Cl2ⁱ	94.99 (7)	C10—C9—H9	120.0
S—Au—F3ⁱⁱ	88.98 (11)	C8—C9—H9	120.0
P—Au—F3ⁱⁱ	107.67 (12)	C11—C10—C9	120.0
Cl2—Au—F3ⁱⁱ	71.87 (12)	C11—C10—H10	120.0
Cl1—Au—F3ⁱⁱ	88.50 (11)	C9—C10—H10	120.0
Cl2ⁱ—Au—F3ⁱⁱ	161.66 (8)	C10—C11—C12	120.0
C6—S—Au	103.2 (2)	C10—C11—H11	120.0
C1—P—C7	106.8 (3)	C12—C11—H11	120.0
C1—P—C13	108.2 (3)	C11—C12—C7	120.0
C7—P—C13	110.8 (2)	C11—C12—H12	120.0
C1—P—Au	104.6 (2)	C7—C12—H12	120.0
C7—P—Au	111.53 (17)	C14—C13—C18	120.0
C13—P—Au	114.36 (18)	C14—C13—P	120.0 (2)
C6—C1—C2	119.7 (6)	C18—C13—P	120.0 (2)
C6—C1—P	118.5 (5)	C15—C14—C13	120.0
C2—C1—P	121.8 (5)	C15—C14—H14	120.0
F2—C2—C3	119.1 (6)	C13—C14—H14	120.0
F2—C2—C1	119.9 (6)	C16—C15—C14	120.0
C3—C2—C1	121.0 (7)	C16—C15—H15	120.0
C4—C3—C2	119.7 (7)	C14—C15—H15	120.0
C4—C3—F3	120.0 (7)	C17—C16—C15	120.0
C2—C3—F3	120.3 (7)	C17—C16—H16	120.0
F4—C4—C3	119.5 (7)	C15—C16—H16	120.0
F4—C4—C5	120.2 (7)	C16—C17—C18	120.0
C3—C4—C5	120.2 (6)	C16—C17—H17	120.0
C6—C5—F5	120.3 (7)	C18—C17—H17	120.0
C6—C5—C4	121.4 (6)	C17—C18—C13	120.0
F5—C5—C4	118.3 (6)	C17—C18—H18	120.0
C5—C6—C1	118.0 (6)	C13—C18—H18	120.0

Symmetry codes: (i) −x, −y, −z; (ii) x, y−1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···F3ⁱⁱ	0.93	2.60	3.444 (7)	151
C18—H18···F4ⁱⁱⁱ	0.93	2.50	3.082 (7)	121

Symmetry codes: (ii) x, y−1, z; (iii) x+1/2, y−1/2, z.

Selected geometric parameters (Å, º) top

Au—S	2.273 (3)	Au—Cl2	2.337 (3)
Au—P	2.258 (3)	Au—Cl1	2.305 (3)

S—Au—P	90.22 (10)	Cl2—Au—Cl1	93.88 (11)
S—Au—Cl2	87.51 (10)	S—Au—Cl2ⁱ	88.12 (7)
P—Au—Cl2	177.69 (6)	P—Au—Cl2ⁱ	90.45 (9)
S—Au—Cl1	176.59 (7)	Cl2—Au—Cl2ⁱ	89.91 (9)
P—Au—Cl1	88.36 (10)	Cl1—Au—Cl2ⁱ	94.99 (7)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···F3ⁱⁱ	0.93	2.60	3.444 (7)	150.6
C18—H18···F4ⁱⁱⁱ	0.93	2.50	3.082 (7)	120.9

Symmetry codes: (ii) x, y−1, z; (iii) x+1/2, y−1/2, z.

Acknowledgements

We are grateful for the provision of a crystalline sample by Gary P. Eller and Devon W. Meek, as well as support from the National Science Foundation through equipment grant GP8534 awarded to the Ohio State University where the experimental work was carried out.

References

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Volume 71| Part 10| October 2015| Pages m181-m182

doi:10.1107/S2056989015016758

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