3,4,5-Trimethyl-2,4,6-triphenyl-4H-thio­pyran

Rahmani, H.; Pirelahi, H.; Ng, S.W.

doi:10.1107/S1600536809005923

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o604

doi:10.1107/S1600536809005923

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3,4,5-Trimethyl-2,4,6-triphenyl-4H-thiopyran

Hossein Rahmani,^a Hooshang Pirelahi ^b and Seik Weng Ng ^c ^*

^aInstitute of Chemical Industries, Iranian Research Organization for Science and Technology, PO Box 15815-358, Tehran, Iran, ^bDepartment of Chemistry, College of Science, University of Tehran, PO Box 13145-143, Tehran, Iran, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 18 February 2009; accepted 19 February 2009; online 25 February 2009)

The six-membered thiopyran ring in the title compound, C₂₆H₂₄S, adopts a boat conformation, with the S atom displaced by 0.478 (2) Å and the 3-methylene C atom by 0.644 (2) Å from the plane of the other four sp²-hydridized C atoms. The methyl group on the methylene carbon lies in a pseudo-equatorial position and the phenyl ring in a pseudo-axial position.

Related literature

For a similar compound, see: Rahmani et al. (2009 ). For the synthesis, see: Rahmani & Pirelahi (1997 ).

Experimental

Crystal data

C₂₆H₂₄S
M_r = 368.51
Monoclinic, P 2₁ /n
a = 8.4525 (1) Å
b = 14.4732 (2) Å
c = 16.2971 (3) Å
β = 103.156 (1)°
V = 1941.37 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 115 K
0.35 × 0.35 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.840, T_max = 0.966
17659 measured reflections
4445 independent reflections
3576 reflections with I > σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.123
S = 1.05
4445 reflections
247 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809005923/sj2579sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809005923/sj2579Isup2.hkl

checkCIF report

Related literature top

For a similar compound, see: Rahmani et al. (2009). For the synthesis, see: Rahmani & Pirelahi (1997).

Experimental top

4-Methyl-2,4,6-triphenyl-4H-thiopyran was was synthesized by the reaction of methyl magnesium bromide and 3,5-dimethyl-2,4,6triphenyl thiopyrylium perchlorate in dry ether under an argon atmosphere according to a reported method (Rahmani & Pirelahi, 1997). The product was isolated by TLC on neutral alumina (petroleum ether 40–60 °C) and purified by recrystalization from ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. Thermal ellisoid plot (Barbour, 2001) of C₂₆H₂₄S; probability levels are set at 70% and H-atoms are drawn as spheres of arbitrary radius.

3,4,5-Trimethyl-2,4,6-triphenyl-4H-thiopyran top

Crystal data top

C₂₆H₂₄S	F(000) = 784
M_r = 368.51	D_x = 1.261 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5510 reflections
a = 8.4525 (1) Å	θ = 2.5–28.2°
b = 14.4732 (2) Å	µ = 0.17 mm⁻¹
c = 16.2971 (3) Å	T = 115 K
β = 103.156 (1)°	Block, colorless
V = 1941.37 (5) Å³	0.35 × 0.35 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	4445 independent reflections
Radiation source: fine-focus sealed tube	3576 reflections with I > σ(I)
Graphite monochromator	R_int = 0.037
ω scans	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.840, T_max = 0.966	k = −18→18
17659 measured reflections	l = −21→21

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.059P)² + 1.0605P] where P = (F_o² + 2F_c²)/3
4445 reflections	(Δ/σ)_max = 0.001
247 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₂₆H₂₄S	V = 1941.37 (5) Å³
M_r = 368.51	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.4525 (1) Å	µ = 0.17 mm⁻¹
b = 14.4732 (2) Å	T = 115 K
c = 16.2971 (3) Å	0.35 × 0.35 × 0.20 mm
β = 103.156 (1)°

Data collection top

Bruker SMART APEX diffractometer	4445 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3576 reflections with I > σ(I)
T_min = 0.840, T_max = 0.966	R_int = 0.037
17659 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 1.05	Δρ_max = 0.39 e Å⁻³
4445 reflections	Δρ_min = −0.36 e Å⁻³
247 parameters

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

	x	y	z	U_iso*/U_eq
S1	0.66266 (5)	0.60193 (3)	0.30451 (3)	0.01781 (12)
C1	0.56658 (19)	0.69496 (11)	0.34341 (10)	0.0168 (3)
C2	0.4182 (2)	0.68372 (11)	0.35910 (10)	0.0170 (3)
C3	0.32243 (19)	0.59530 (11)	0.32806 (11)	0.0165 (3)
C4	0.4297 (2)	0.51230 (12)	0.36251 (10)	0.0174 (3)
C5	0.5796 (2)	0.50682 (11)	0.34781 (10)	0.0166 (3)
C6	0.3438 (2)	0.75486 (13)	0.40643 (12)	0.0231 (4)
H6A	0.4224	0.8045	0.4257	0.035*
H6B	0.3145	0.7257	0.4552	0.035*
H6C	0.2462	0.7806	0.3692	0.035*
C7	0.1580 (2)	0.59255 (13)	0.35402 (12)	0.0223 (4)
H7A	0.1768	0.5943	0.4156	0.033*
H7B	0.1002	0.5356	0.3329	0.033*
H7C	0.0924	0.6460	0.3300	0.033*
C8	0.3661 (2)	0.43945 (13)	0.41291 (11)	0.0224 (4)
H8A	0.4540	0.3966	0.4374	0.034*
H8B	0.2777	0.4053	0.3759	0.034*
H8C	0.3253	0.4691	0.4581	0.034*
C9	0.6879 (2)	0.42489 (11)	0.36408 (10)	0.0173 (3)
C10	0.6295 (2)	0.33811 (12)	0.33442 (11)	0.0228 (4)
H10	0.5200	0.3320	0.3038	0.027*
C11	0.7283 (2)	0.26059 (13)	0.34882 (12)	0.0281 (4)
H11	0.6859	0.2019	0.3289	0.034*
C12	0.8894 (2)	0.26882 (13)	0.39231 (13)	0.0287 (4)
H12	0.9577	0.2159	0.4021	0.034*
C13	0.9494 (2)	0.35449 (14)	0.42122 (12)	0.0261 (4)
H13	1.0595	0.3602	0.4510	0.031*
C14	0.8508 (2)	0.43231 (13)	0.40722 (11)	0.0202 (4)
H14	0.8941	0.4909	0.4270	0.024*
C15	0.27841 (19)	0.59420 (11)	0.23067 (11)	0.0165 (3)
C16	0.2352 (2)	0.67542 (12)	0.18567 (12)	0.0240 (4)
H16	0.2420	0.7325	0.2151	0.029*
C17	0.1825 (2)	0.67490 (13)	0.09868 (12)	0.0270 (4)
H17	0.1534	0.7312	0.0692	0.032*
C18	0.1722 (2)	0.59257 (12)	0.05465 (11)	0.0219 (4)
H18	0.1364	0.5921	−0.0050	0.026*
C19	0.2142 (2)	0.51143 (12)	0.09817 (11)	0.0219 (4)
H19	0.2074	0.4546	0.0684	0.026*
C20	0.2667 (2)	0.51212 (12)	0.18537 (11)	0.0201 (4)
H20	0.2951	0.4555	0.2145	0.024*
C21	0.6639 (2)	0.78164 (11)	0.35383 (10)	0.0178 (3)
C22	0.8276 (2)	0.78257 (12)	0.39556 (11)	0.0201 (4)
H22	0.8794	0.7268	0.4178	0.024*
C23	0.9153 (2)	0.86471 (13)	0.40479 (12)	0.0237 (4)
H23	1.0261	0.8647	0.4342	0.028*
C24	0.8427 (2)	0.94655 (13)	0.37156 (12)	0.0251 (4)
H24	0.9032	1.0025	0.3779	0.030*
C25	0.6807 (2)	0.94582 (13)	0.32899 (11)	0.0240 (4)
H25	0.6298	1.0016	0.3061	0.029*
C26	0.5927 (2)	0.86423 (12)	0.31960 (11)	0.0207 (4)
H26	0.4824	0.8645	0.2895	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0159 (2)	0.0162 (2)	0.0235 (2)	0.00008 (15)	0.00897 (16)	0.00014 (16)
C1	0.0155 (8)	0.0169 (8)	0.0175 (8)	0.0015 (6)	0.0030 (6)	−0.0009 (6)
C2	0.0155 (8)	0.0177 (8)	0.0174 (8)	0.0014 (6)	0.0034 (6)	−0.0006 (6)
C3	0.0118 (7)	0.0179 (8)	0.0207 (8)	−0.0009 (6)	0.0054 (6)	−0.0014 (6)
C4	0.0168 (8)	0.0188 (8)	0.0163 (8)	−0.0016 (6)	0.0030 (6)	−0.0007 (6)
C5	0.0166 (8)	0.0163 (8)	0.0170 (8)	−0.0015 (6)	0.0037 (6)	0.0009 (6)
C6	0.0193 (9)	0.0250 (9)	0.0262 (9)	−0.0004 (7)	0.0077 (7)	−0.0062 (7)
C7	0.0153 (8)	0.0278 (9)	0.0254 (9)	−0.0012 (7)	0.0082 (7)	−0.0013 (7)
C8	0.0193 (9)	0.0247 (9)	0.0244 (9)	−0.0028 (7)	0.0075 (7)	0.0031 (7)
C9	0.0164 (8)	0.0189 (8)	0.0177 (8)	0.0008 (6)	0.0062 (6)	0.0019 (6)
C10	0.0217 (9)	0.0229 (9)	0.0237 (9)	−0.0003 (7)	0.0050 (7)	−0.0012 (7)
C11	0.0338 (11)	0.0217 (9)	0.0317 (10)	0.0018 (8)	0.0133 (9)	0.0009 (8)
C12	0.0294 (10)	0.0257 (10)	0.0351 (10)	0.0113 (8)	0.0160 (8)	0.0091 (8)
C13	0.0177 (9)	0.0349 (11)	0.0267 (9)	0.0053 (8)	0.0069 (7)	0.0094 (8)
C14	0.0161 (8)	0.0244 (9)	0.0210 (8)	−0.0016 (7)	0.0058 (7)	0.0023 (7)
C15	0.0092 (7)	0.0202 (8)	0.0207 (8)	−0.0001 (6)	0.0044 (6)	0.0002 (6)
C16	0.0274 (9)	0.0162 (8)	0.0263 (9)	0.0046 (7)	0.0016 (7)	−0.0038 (7)
C17	0.0314 (10)	0.0194 (9)	0.0271 (10)	0.0042 (7)	0.0000 (8)	0.0032 (7)
C18	0.0181 (8)	0.0265 (9)	0.0200 (8)	0.0004 (7)	0.0019 (7)	−0.0008 (7)
C19	0.0207 (8)	0.0186 (8)	0.0251 (9)	−0.0001 (7)	0.0027 (7)	−0.0044 (7)
C20	0.0188 (8)	0.0167 (8)	0.0239 (9)	−0.0007 (6)	0.0030 (7)	0.0014 (7)
C21	0.0177 (8)	0.0193 (8)	0.0177 (8)	−0.0010 (6)	0.0067 (6)	−0.0012 (6)
C22	0.0172 (8)	0.0211 (9)	0.0221 (8)	0.0012 (6)	0.0050 (7)	0.0000 (7)
C23	0.0160 (8)	0.0286 (10)	0.0267 (9)	−0.0041 (7)	0.0050 (7)	−0.0019 (7)
C24	0.0271 (10)	0.0227 (9)	0.0277 (10)	−0.0061 (7)	0.0106 (8)	−0.0022 (7)
C25	0.0274 (10)	0.0195 (9)	0.0256 (9)	−0.0002 (7)	0.0070 (8)	0.0038 (7)
C26	0.0188 (8)	0.0223 (9)	0.0207 (8)	0.0004 (7)	0.0039 (7)	−0.0005 (7)

Geometric parameters (Å, º) top

S1—C1	1.7631 (17)	C12—C13	1.381 (3)
S1—C5	1.7638 (16)	C12—H12	0.9500
C1—C2	1.346 (2)	C13—C14	1.389 (3)
C1—C21	1.488 (2)	C13—H13	0.9500
C2—C6	1.507 (2)	C14—H14	0.9500
C2—C3	1.537 (2)	C15—C16	1.390 (2)
C3—C4	1.532 (2)	C15—C20	1.390 (2)
C3—C7	1.543 (2)	C16—C17	1.386 (3)
C3—C15	1.546 (2)	C16—H16	0.9500
C4—C5	1.345 (2)	C17—C18	1.383 (2)
C4—C8	1.509 (2)	C17—H17	0.9500
C5—C9	1.485 (2)	C18—C19	1.376 (2)
C6—H6A	0.9800	C18—H18	0.9500
C6—H6B	0.9800	C19—C20	1.389 (2)
C6—H6C	0.9800	C19—H19	0.9500
C7—H7A	0.9800	C20—H20	0.9500
C7—H7B	0.9800	C21—C26	1.396 (2)
C7—H7C	0.9800	C21—C22	1.397 (2)
C8—H8A	0.9800	C22—C23	1.391 (2)
C8—H8B	0.9800	C22—H22	0.9500
C8—H8C	0.9800	C23—C24	1.386 (3)
C9—C10	1.395 (2)	C23—H23	0.9500
C9—C14	1.400 (2)	C24—C25	1.387 (3)
C10—C11	1.387 (3)	C24—H24	0.9500
C10—H10	0.9500	C25—C26	1.386 (2)
C11—C12	1.389 (3)	C25—H25	0.9500
C11—H11	0.9500	C26—H26	0.9500

C1—S1—C5	101.20 (8)	C13—C12—C11	119.49 (17)
C2—C1—C21	126.50 (15)	C13—C12—H12	120.3
C2—C1—S1	120.10 (13)	C11—C12—H12	120.3
C21—C1—S1	113.39 (12)	C12—C13—C14	120.77 (17)
C1—C2—C6	122.02 (15)	C12—C13—H13	119.6
C1—C2—C3	118.81 (14)	C14—C13—H13	119.6
C6—C2—C3	119.17 (14)	C13—C14—C9	120.34 (17)
C4—C3—C2	107.98 (13)	C13—C14—H14	119.8
C4—C3—C7	111.96 (14)	C9—C14—H14	119.8
C2—C3—C7	111.78 (13)	C16—C15—C20	117.66 (16)
C4—C3—C15	110.63 (13)	C16—C15—C3	120.41 (15)
C2—C3—C15	109.40 (13)	C20—C15—C3	121.70 (15)
C7—C3—C15	105.07 (13)	C17—C16—C15	121.32 (16)
C5—C4—C8	121.52 (15)	C17—C16—H16	119.3
C5—C4—C3	118.93 (14)	C15—C16—H16	119.3
C8—C4—C3	119.54 (14)	C18—C17—C16	120.20 (17)
C4—C5—C9	125.67 (15)	C18—C17—H17	119.9
C4—C5—S1	120.16 (13)	C16—C17—H17	119.9
C9—C5—S1	114.17 (12)	C19—C18—C17	119.29 (17)
C2—C6—H6A	109.5	C19—C18—H18	120.4
C2—C6—H6B	109.5	C17—C18—H18	120.4
H6A—C6—H6B	109.5	C18—C19—C20	120.40 (16)
C2—C6—H6C	109.5	C18—C19—H19	119.8
H6A—C6—H6C	109.5	C20—C19—H19	119.8
H6B—C6—H6C	109.5	C19—C20—C15	121.13 (16)
C3—C7—H7A	109.5	C19—C20—H20	119.4
C3—C7—H7B	109.5	C15—C20—H20	119.4
H7A—C7—H7B	109.5	C26—C21—C22	118.38 (16)
C3—C7—H7C	109.5	C26—C21—C1	119.97 (15)
H7A—C7—H7C	109.5	C22—C21—C1	121.63 (15)
H7B—C7—H7C	109.5	C23—C22—C21	120.38 (16)
C4—C8—H8A	109.5	C23—C22—H22	119.8
C4—C8—H8B	109.5	C21—C22—H22	119.8
H8A—C8—H8B	109.5	C24—C23—C22	120.70 (17)
C4—C8—H8C	109.5	C24—C23—H23	119.6
H8A—C8—H8C	109.5	C22—C23—H23	119.6
H8B—C8—H8C	109.5	C23—C24—C25	119.19 (17)
C10—C9—C14	118.23 (16)	C23—C24—H24	120.4
C10—C9—C5	120.13 (15)	C25—C24—H24	120.4
C14—C9—C5	121.62 (15)	C26—C25—C24	120.39 (17)
C11—C10—C9	121.18 (17)	C26—C25—H25	119.8
C11—C10—H10	119.4	C24—C25—H25	119.8
C9—C10—H10	119.4	C25—C26—C21	120.93 (16)
C10—C11—C12	119.97 (18)	C25—C26—H26	119.5
C10—C11—H11	120.0	C21—C26—H26	119.5
C12—C11—H11	120.0

C5—S1—C1—C2	−29.19 (15)	C10—C11—C12—C13	0.3 (3)
C5—S1—C1—C21	151.99 (12)	C11—C12—C13—C14	−0.1 (3)
C21—C1—C2—C6	−12.4 (3)	C12—C13—C14—C9	0.6 (3)
S1—C1—C2—C6	168.91 (13)	C10—C9—C14—C13	−1.3 (2)
C21—C1—C2—C3	167.85 (15)	C5—C9—C14—C13	−179.74 (16)
S1—C1—C2—C3	−10.8 (2)	C4—C3—C15—C16	−156.56 (15)
C1—C2—C3—C4	54.54 (19)	C2—C3—C15—C16	−37.7 (2)
C6—C2—C3—C4	−125.18 (16)	C7—C3—C15—C16	82.42 (18)
C1—C2—C3—C7	178.12 (15)	C4—C3—C15—C20	29.1 (2)
C6—C2—C3—C7	−1.6 (2)	C2—C3—C15—C20	147.93 (15)
C1—C2—C3—C15	−65.93 (19)	C7—C3—C15—C20	−91.92 (18)
C6—C2—C3—C15	114.35 (16)	C20—C15—C16—C17	−0.1 (3)
C2—C3—C4—C5	−54.04 (19)	C3—C15—C16—C17	−174.63 (16)
C7—C3—C4—C5	−177.52 (15)	C15—C16—C17—C18	−0.1 (3)
C15—C3—C4—C5	65.65 (19)	C16—C17—C18—C19	0.2 (3)
C2—C3—C4—C8	125.17 (16)	C17—C18—C19—C20	−0.1 (3)
C7—C3—C4—C8	1.7 (2)	C18—C19—C20—C15	−0.1 (3)
C15—C3—C4—C8	−115.13 (16)	C16—C15—C20—C19	0.2 (3)
C8—C4—C5—C9	11.4 (3)	C3—C15—C20—C19	174.69 (15)
C3—C4—C5—C9	−169.35 (15)	C2—C1—C21—C26	−49.4 (2)
C8—C4—C5—S1	−169.24 (13)	S1—C1—C21—C26	129.31 (14)
C3—C4—C5—S1	10.0 (2)	C2—C1—C21—C22	132.24 (18)
C1—S1—C5—C4	29.71 (15)	S1—C1—C21—C22	−49.03 (19)
C1—S1—C5—C9	−150.90 (12)	C26—C21—C22—C23	2.0 (2)
C4—C5—C9—C10	50.0 (2)	C1—C21—C22—C23	−179.63 (16)
S1—C5—C9—C10	−129.34 (15)	C21—C22—C23—C24	−1.1 (3)
C4—C5—C9—C14	−131.58 (18)	C22—C23—C24—C25	0.2 (3)
S1—C5—C9—C14	49.07 (19)	C23—C24—C25—C26	−0.2 (3)
C14—C9—C10—C11	1.5 (3)	C24—C25—C26—C21	1.1 (3)
C5—C9—C10—C11	179.99 (16)	C22—C21—C26—C25	−2.0 (3)
C9—C10—C11—C12	−1.0 (3)	C1—C21—C26—C25	179.61 (16)

Experimental details

Crystal data
Chemical formula	C₂₆H₂₄S
M_r	368.51
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	115
a, b, c (Å)	8.4525 (1), 14.4732 (2), 16.2971 (3)
β (°)	103.156 (1)
V (Å³)	1941.37 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.35 × 0.35 × 0.20

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.840, 0.966
No. of measured, independent and observed [I > σ(I)] reflections	17659, 4445, 3576
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.123, 1.05
No. of reflections	4445
No. of parameters	247
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.36

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Acknowledgements

We thank the Iranian Research Organization for Science and Technology and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Rahmani, H. & Pirelahi, H. (1997). Sulfur Lett. 20, 159–163. CAS Google Scholar
Rahmani, H., Pirelahi, H. & Ng, S. W. (2009). Acta Cryst. E65, o603. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar