(Z)-(1,2-Dichloro­vin­yl)diphenyl­phosphine oxide

Ma, J.-Y.; Feng, Q.-Q.; Wu, M.-S.

doi:10.1107/S1600536811030765

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2267

doi:10.1107/S1600536811030765

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(Z)-(1,2-Dichlorovinyl)diphenylphosphine oxide

Jing-Ya Ma,^a Qing-Qin Feng ^b and Ming-Shu Wu ^a ^*

^aCollege of Chemistry & Chemical Engineering, Hainan Normal University, Haikou 571158, People's Republic of China, and ^bCollege of Chemistry & Chemical Engineering, Anyang Normal University, Anyang 455000, Henan, People's Republic of China
^*Correspondence e-mail: wumingshu@126.com

(Received 15 July 2011; accepted 31 July 2011; online 6 August 2011)

The title compound, C₁₄H₁₁Cl₂OP, was synthesized by the reaction of diphenylphosphine oxide with 1,2-dichloroethyne under CuI catalysis. The reaction provided the Z isomer regioselectively. Two O—P—C bond angles [114.3 (1) and 112.5 (1)°] are significantly larger than the C—P—C [107.7 (1), 105.6 (1) and 106.6 (1)°] and another O—P—C angle [109.5 (1)°], indicating significant distortion of the tetrahedral configuration of the P atom. In the crystal, molecules are linked by weak intermolecular C—H⋯O hydrogen bonds into centrosymmetric dimers, which are connected by further C—H⋯O interactions into chains along [101].

Related literature

For the antimicrobial, insecticidal and anti-inflammatory activity of alkenylphosphine oxides, see: Haynes et al. (1989 , 1991 ); Shi et al. (2000 ); Taylor et al. (2006 ); Rahman et al. (2000 ). For their use as intermediates in the preparation of some palladium catalysts, see: Inoue et al. (2002 ). Nucleophiles, such as amines (Rahman et al., 2000, 2004 ), phosphines (Barbaro et al., 2002 ; Alajarin et al., 2004 ; Han & Zhao, 2005 ) and carbanion species readily add to the olefinic bond in alkenylphosphine oxides to give useful bifunctional adducts.

Experimental

Crystal data

C₁₄H₁₁Cl₂OP
M_r = 297.10
Monoclinic, P 2₁ /n
a = 12.0621 (11) Å
b = 7.9521 (8) Å
c = 14.9913 (15) Å
β = 102.858 (1)°
V = 1401.9 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.56 mm⁻¹
T = 298 K
0.45 × 0.40 × 0.32 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ) T_min = 0.786, T_max = 0.841
6788 measured reflections
2475 independent reflections
2009 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.094
S = 1.08
2475 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1ⁱ	0.93	2.51	3.138 (3)	125
C8—H8⋯O1ⁱⁱ	0.93	2.57	3.344 (4)	141
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811030765/ld2021sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811030765/ld2021Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811030765/ld2021Isup3.cml

checkCIF report

Comment top

Alkenylphosphine oxides have attracted much attention because they are used as biologically active compounds (Haynes et al., 1989; Haynes et al., 1991; Shi et al., 2000), and are the key intermediates for preparation of some palladium catalysts (Inoue et al.,2002). Nucleophiles, such as amines (Rahman et al., 2000; Rahman et al., 2004), phosphines (Barbaro et al., 2002; Alajarin et al., 2004; Han & Zhao, 2005) and carbanion species readily add to the olefinic bond in alkenylphosphine oxides to give useful bifunctional adducts. In order to further confirm stereostructure and structure-activity relationship of alkenylphosphine oxides, we performed the synthesis of the title compound by addition reaction of the diphenylphosphine oxide with 1,2-dichloroethyne under catalysis of commercially available CuI at room temperature. The reaction provided (Z)-(1,2-dichlorovinyl)diphenylphosphine oxide regioselectively. The study of the crystal structure of the title compound was commenced to establish its structural features that can be helpful for its practical applications. In the title molecule (Fig. 1), the bond angles O(1)–P(1)–C(11)(114.31 (10)°) and O(1)–P(1)–C(5)(112.55 (10)°) are significantly larger than C(11)–P(1)–C(5)(107.75 (10)°), O(1)–P(1)–C(1)(109.54 (10)°), C(11)–P(1)–C(1)(105.58 (10)°), and C(5)–P(1)–C(1) (106.62 (10)°), indicating that sp³-hybridized P atom adopts distorted tetrahedral configuration. In the crystal, molecules are linked by weak intermolecular C-H···O hydrogen bonds in centrosymmetric dimers further connected in chains along [1 0 1].

Related literature top

For the antimicrobial, insecticidal and anti-inflammatory activity of alkenylphosphine oxides, see: Haynes et al. (1989, 1991); Shi et al. (2000); Taylor et al. (2006); Rahman et al. (2000). For their use as intermediates in the preparation of some palladium catalysts, see: Inoue et al. (2002). Nucleophiles, such as amines (Rahman et al., 2000, 2004), phosphines (Barbaro et al., 2002; Alajarin et al., 2004; Han & Zhao, 2005) and carbanion species readily add to the olefinic bond in alkenylphosphine oxides to give useful bifunctional adducts.

Experimental top

To a stirred solution of 1,2-dichloroethyne (1.88 g, 20 mmol) in anhydrous ether (40 ml), a solution of diphenylphosphine oxide (2.23g, 12mmol) in ether (10 ml) was added dropwise in the presence of CuI (0.229g, 1.2 mmol) at room temperature in nitrogen atmosphere for 4h. After completion of the reaction as indicated by thin-layer chromatography, the mixture was filtered and rinsed with ethyl acetate. The organic layer was washed with brine and dried over MgSO₄. The title product was obtained by crystallization as colourless solid. The product obtained was purified by flash chromatograghy. Single crystals of the title compound suitable for single-crystal X-ray analysis were obtained by recrystallization from ether.

Computing details top

Data collection: APEX2 (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. Crystal packing of the title compound, viewed down the b direction Intermolecular hydrogen bonds are shown as dashed lines.

(Z)-(1,2-Dichlorovinyl)diphenylphosphine oxide top

Crystal data top

C₁₄H₁₁Cl₂OP	F(000) = 608
M_r = 297.10	D_x = 1.408 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.0621 (11) Å	Cell parameters from 3636 reflections
b = 7.9521 (8) Å	θ = 2.5–28.0°
c = 14.9913 (15) Å	µ = 0.56 mm⁻¹
β = 102.858 (1)°	T = 298 K
V = 1401.9 (2) Å³	Prism, colourless
Z = 4	0.45 × 0.40 × 0.32 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	2475 independent reflections
Radiation source: fine-focus sealed tube	2009 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −14→11
T_min = 0.786, T_max = 0.841	k = −9→9
6788 measured reflections	l = −12→17

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.094	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0395P)² + 0.729P] where P = (F_o² + 2F_c²)/3
2475 reflections	(Δ/σ)_max = 0.001
163 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₁₄H₁₁Cl₂OP	V = 1401.9 (2) Å³
M_r = 297.10	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.0621 (11) Å	µ = 0.56 mm⁻¹
b = 7.9521 (8) Å	T = 298 K
c = 14.9913 (15) Å	0.45 × 0.40 × 0.32 mm
β = 102.858 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2475 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	2009 reflections with I > 2σ(I)
T_min = 0.786, T_max = 0.841	R_int = 0.022
6788 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.094	H-atom parameters constrained
S = 1.08	Δρ_max = 0.28 e Å⁻³
2475 reflections	Δρ_min = −0.37 e Å⁻³
163 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
Cl1	0.64091 (5)	0.30633 (8)	0.48897 (6)	0.0610 (2)
Cl2	0.87750 (6)	0.09961 (8)	0.52709 (5)	0.0558 (2)
O1	0.90014 (13)	0.6840 (2)	0.53670 (11)	0.0441 (4)
P1	0.77986 (4)	0.62950 (7)	0.51027 (4)	0.03243 (16)
C1	0.77287 (18)	0.4017 (3)	0.51179 (15)	0.0340 (5)
C2	0.8685 (2)	0.3151 (3)	0.52622 (15)	0.0386 (5)
H2	0.9363	0.3754	0.5367	0.046*
C5	0.71157 (19)	0.6946 (3)	0.39607 (15)	0.0358 (5)
C6	0.7790 (2)	0.7721 (3)	0.34425 (18)	0.0528 (7)
H6	0.8557	0.7909	0.3694	0.063*
C7	0.7327 (3)	0.8213 (4)	0.2555 (2)	0.0726 (9)
H7	0.7782	0.8733	0.2211	0.087*
C8	0.6190 (3)	0.7938 (4)	0.2178 (2)	0.0693 (9)
H8	0.5883	0.8266	0.1579	0.083*
C9	0.5516 (2)	0.7187 (4)	0.26807 (19)	0.0580 (7)
H9	0.4749	0.7011	0.2422	0.070*
C10	0.5964 (2)	0.6681 (3)	0.35770 (17)	0.0462 (6)
H10	0.5500	0.6171	0.3918	0.055*
C11	0.69328 (18)	0.7001 (3)	0.58622 (15)	0.0357 (5)
C12	0.6898 (3)	0.6104 (3)	0.66513 (18)	0.0570 (7)
H12	0.7270	0.5076	0.6761	0.068*
C13	0.6313 (3)	0.6733 (4)	0.7274 (2)	0.0720 (9)
H13	0.6287	0.6122	0.7798	0.086*
C14	0.5770 (3)	0.8255 (4)	0.7119 (2)	0.0646 (8)
H14	0.5375	0.8672	0.7538	0.078*
C15	0.5807 (2)	0.9163 (4)	0.6352 (2)	0.0574 (7)
H15	0.5446	1.0202	0.6255	0.069*
C16	0.6382 (2)	0.8539 (3)	0.57215 (17)	0.0450 (6)
H16	0.6399	0.9157	0.5198	0.054*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0402 (4)	0.0432 (4)	0.0962 (6)	−0.0081 (3)	0.0078 (3)	0.0024 (3)
Cl2	0.0635 (4)	0.0370 (3)	0.0740 (5)	0.0102 (3)	0.0305 (4)	0.0031 (3)
O1	0.0339 (8)	0.0455 (9)	0.0512 (10)	−0.0043 (7)	0.0057 (7)	−0.0002 (8)
P1	0.0304 (3)	0.0327 (3)	0.0339 (3)	−0.0002 (2)	0.0064 (2)	0.0015 (2)
C1	0.0356 (12)	0.0325 (11)	0.0348 (12)	−0.0024 (9)	0.0100 (9)	−0.0005 (9)
C2	0.0436 (13)	0.0330 (12)	0.0430 (14)	0.0015 (10)	0.0181 (11)	0.0019 (10)
C5	0.0396 (12)	0.0333 (11)	0.0351 (12)	0.0037 (9)	0.0095 (10)	0.0002 (9)
C6	0.0531 (15)	0.0594 (16)	0.0476 (15)	−0.0026 (13)	0.0152 (12)	0.0103 (13)
C7	0.088 (2)	0.086 (2)	0.0489 (18)	0.0013 (18)	0.0252 (16)	0.0236 (16)
C8	0.088 (2)	0.078 (2)	0.0381 (16)	0.0183 (18)	0.0070 (16)	0.0105 (15)
C9	0.0536 (16)	0.0668 (18)	0.0458 (16)	0.0115 (14)	−0.0053 (13)	−0.0015 (14)
C10	0.0438 (14)	0.0517 (14)	0.0422 (14)	0.0045 (11)	0.0078 (11)	0.0023 (12)
C11	0.0358 (12)	0.0386 (12)	0.0313 (12)	−0.0010 (9)	0.0046 (9)	−0.0027 (10)
C12	0.0811 (19)	0.0525 (15)	0.0396 (14)	0.0128 (14)	0.0181 (13)	0.0058 (12)
C13	0.104 (3)	0.078 (2)	0.0404 (16)	−0.0032 (19)	0.0308 (17)	−0.0010 (15)
C14	0.0630 (18)	0.082 (2)	0.0546 (18)	−0.0031 (16)	0.0253 (14)	−0.0256 (16)
C15	0.0553 (16)	0.0576 (16)	0.0591 (18)	0.0106 (13)	0.0122 (14)	−0.0158 (14)
C16	0.0478 (14)	0.0424 (13)	0.0443 (14)	0.0025 (11)	0.0089 (11)	−0.0008 (11)

Geometric parameters (Å, º) top

Cl1—C1	1.727 (2)	C8—H8	0.9300
Cl2—C2	1.717 (2)	C9—C10	1.391 (4)
O1—P1	1.4813 (16)	C9—H9	0.9300
P1—C11	1.798 (2)	C10—H10	0.9300
P1—C5	1.803 (2)	C11—C16	1.385 (3)
P1—C1	1.814 (2)	C11—C12	1.390 (3)
C1—C2	1.319 (3)	C12—C13	1.382 (4)
C2—H2	0.9300	C12—H12	0.9300
C5—C6	1.388 (3)	C13—C14	1.371 (5)
C5—C10	1.397 (3)	C13—H13	0.9300
C6—C7	1.380 (4)	C14—C15	1.366 (4)
C6—H6	0.9300	C14—H14	0.9300
C7—C8	1.379 (5)	C15—C16	1.384 (4)
C7—H7	0.9300	C15—H15	0.9300
C8—C9	1.364 (4)	C16—H16	0.9300

O1—P1—C11	114.31 (10)	C8—C9—C10	120.6 (3)
O1—P1—C5	112.55 (10)	C8—C9—H9	119.7
C11—P1—C5	107.75 (10)	C10—C9—H9	119.7
O1—P1—C1	109.54 (10)	C9—C10—C5	119.4 (2)
C11—P1—C1	105.58 (10)	C9—C10—H10	120.3
C5—P1—C1	106.62 (10)	C5—C10—H10	120.3
C2—C1—Cl1	122.49 (18)	C16—C11—C12	118.6 (2)
C2—C1—P1	118.80 (17)	C16—C11—P1	120.36 (18)
Cl1—C1—P1	118.64 (12)	C12—C11—P1	120.72 (18)
C1—C2—Cl2	124.99 (19)	C13—C12—C11	120.4 (3)
C1—C2—H2	117.5	C13—C12—H12	119.8
Cl2—C2—H2	117.5	C11—C12—H12	119.8
C6—C5—C10	119.3 (2)	C14—C13—C12	120.1 (3)
C6—C5—P1	117.27 (18)	C14—C13—H13	120.0
C10—C5—P1	123.39 (18)	C12—C13—H13	120.0
C7—C6—C5	120.2 (3)	C15—C14—C13	120.4 (3)
C7—C6—H6	119.9	C15—C14—H14	119.8
C5—C6—H6	119.9	C13—C14—H14	119.8
C8—C7—C6	120.2 (3)	C14—C15—C16	120.0 (3)
C8—C7—H7	119.9	C14—C15—H15	120.0
C6—C7—H7	119.9	C16—C15—H15	120.0
C9—C8—C7	120.2 (3)	C15—C16—C11	120.6 (2)
C9—C8—H8	119.9	C15—C16—H16	119.7
C7—C8—H8	119.9	C11—C16—H16	119.7

O1—P1—C1—C2	−6.2 (2)	C7—C8—C9—C10	−0.3 (5)
C11—P1—C1—C2	−129.75 (19)	C8—C9—C10—C5	−0.1 (4)
C5—P1—C1—C2	115.8 (2)	C6—C5—C10—C9	0.5 (4)
O1—P1—C1—Cl1	176.78 (12)	P1—C5—C10—C9	−178.29 (19)
C11—P1—C1—Cl1	53.24 (16)	O1—P1—C11—C16	88.7 (2)
C5—P1—C1—Cl1	−61.18 (16)	C5—P1—C11—C16	−37.2 (2)
Cl1—C1—C2—Cl2	−1.4 (3)	C1—P1—C11—C16	−150.85 (19)
P1—C1—C2—Cl2	−178.31 (13)	O1—P1—C11—C12	−84.5 (2)
O1—P1—C5—C6	5.5 (2)	C5—P1—C11—C12	149.6 (2)
C11—P1—C5—C6	132.48 (19)	C1—P1—C11—C12	35.9 (2)
C1—P1—C5—C6	−114.6 (2)	C16—C11—C12—C13	0.8 (4)
O1—P1—C5—C10	−175.63 (18)	P1—C11—C12—C13	174.1 (2)
C11—P1—C5—C10	−48.7 (2)	C11—C12—C13—C14	−0.6 (5)
C1—P1—C5—C10	64.3 (2)	C12—C13—C14—C15	−0.2 (5)
C10—C5—C6—C7	−0.4 (4)	C13—C14—C15—C16	0.8 (5)
P1—C5—C6—C7	178.4 (2)	C14—C15—C16—C11	−0.6 (4)
C5—C6—C7—C8	0.0 (5)	C12—C11—C16—C15	−0.2 (4)
C6—C7—C8—C9	0.4 (5)	P1—C11—C16—C15	−173.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱ	0.93	2.51	3.138 (3)	125
C8—H8···O1ⁱⁱ	0.93	2.57	3.344 (4)	141

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x−1/2, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁Cl₂OP
M_r	297.10
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	12.0621 (11), 7.9521 (8), 14.9913 (15)
β (°)	102.858 (1)
V (Å³)	1401.9 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.56
Crystal size (mm)	0.45 × 0.40 × 0.32

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2008)
T_min, T_max	0.786, 0.841
No. of measured, independent and observed [I > 2σ(I)] reflections	6788, 2475, 2009
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.094, 1.08
No. of reflections	2475
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.37

Computer programs: APEX2 (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱ	0.93	2.51	3.138 (3)	125.2
C8—H8···O1ⁱⁱ	0.93	2.57	3.344 (4)	140.6

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x−1/2, −y+3/2, z−1/2.

Acknowledgements

This work was supported financially by the construction project of the unit granting doctorates of Hainan Normal University

References

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