9-[4,5-Bis(benzyl­sulfan­yl)-1,3-dithiol-2-yl­idene]-4,5-diaza­fluorene

Zhong, X.-D.; Zhu, Y.-L.; Wu, X.; Jin, J.-Y.; Tang, X.-L.

doi:10.1107/S1600536808018667

organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1353

doi:10.1107/S1600536808018667

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9-[4,5-Bis(benzylsulfanyl)-1,3-dithiol-2-ylidene]-4,5-diazafluorene

Xu-Dong Zhong,^a Yu-Lan Zhu,^a,^b ^* Xue Wu,^a ^* Jing-Yi Jin ^a and Xue-Ling Tang ^a

^aDepartment of Chemistry, College of Science, Yanbian University, Yanji 133002, People's Republic of China, and ^bJiangsu Key Laboratory for the Chemistry of Low-Dimensional Materials, Huaiyin Teachers' College, Huaian 223300, People's Republic of China
^*Correspondence e-mail: yulanzhu2008@126.com,

(Received 29 March 2008; accepted 20 June 2008; online 28 June 2008)

In rhe title compound, C₂₈H₂₀N₂S₄, the 1,3-dithiol-2-ylidene and 4,5-diazafluoren-9-one (dafone) groups are almost coplanar, making a dihedral angle of only 5.65 (4)°. The two benzyl groups are on different sides of the 1,3-dithiol-2-ylidene ring, forming a dihedral angle of 35.54 (2)°.

Related literature

For general synthesis, see: Sako et al. (1996 ); Wong et al. (2005 ); Amriou et al. (2006 ); Baudron & Hosseini (2006 ). For the crystal structures of related compounds, see: Rillema et al. (2007 ); Zhang et al. (2003 ).

Experimental

Crystal data

C₂₈H₂₀N₂S₄
M_r = 512.70
Monoclinic, P 2₁ /c
a = 16.5133 (4) Å
b = 11.4036 (3) Å
c = 13.1406 (3) Å
β = 100.460 (1)°
V = 2435.06 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 296 (2) K
0.30 × 0.15 × 0.15 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.93, T_max = 0.95
22070 measured reflections
4701 independent reflections
3365 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.137
S = 1.00
4701 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808018667/rt2019sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808018667/rt2019Isup2.hkl

checkCIF report

Comment top

The two coordinating nitrogen atoms in dafone have a larger bite distance (2.99 Å) compared to phenanthroline (2.65 Å). The larger N—N bite distance enforced by the rigid five-membered central ring leads to unequal binding by the two nitrogen atoms with small metal ions (Zhang et al., 2003;). The title compound was synthesized illustrating the coordination mode of dafone.

The molecular structure of the title compound was determined by X-ray analysis (Fig. 1). The 1,3-dithiol-2-ylidene and dafone groups in the structure exhibits a near planar geometry with a dihedral angle 5.65°, and can be explained by the steric repulsion between the S of the dithiole and the peri H of dafone. In the experimentally determined structure, the distances between S1—H19 and S2—H13 are 2.578 and 2.597 Å respectively, although this is still less than the sum of the van der Waals radii (2.91 Å). The two benzyl group are located on different sides of the 1,3-dithiol-2-ylidene plane exhibiting a dihedral angle of 35.5° between them. The exocyclic C11=C12 bond is sightly longer [1.364 Å] than the standard olefinic (R₂C=CR₂) bond length of 1.33 Å and is typical for 1,3-dithiol-2-ylidene groups [average 1.36 Å].

Fig.2 shows the packing in the unit cell and two types of π-π interactions of the benzyl groups: offset face-to-face and edge-to-face. The distance Cg···Cg between the centroids of the two adjacent benzyl groups is 6.445 Å for offset face-to-face, 4.882 and 5.118 Å for edge-to-face.

Related literature top

For general synthesis, see: Sako et al. (1996); Wong et al. (2005); Amriou et al. (2006); Baudron & Hosseini (2006). For the crystal structures of related compounds, see: Rillema et al. (2007); Zhang et al. (2003).

Experimental top

Dafone was synthesized by the oxidation of 1,10-phenanthroline with alkaline potassium permanganate in 40.6% yields according to the procedure reported in literature (Wong et al., 2005;). The cross coupling reaction of dafone with the corresponding 4,5-bis(benzylthio)-1,3-dithione- 2-thione in the presence of triethyl phosphite under a nitrogen atmosphere afforded the title compound along with the mixture of the selfcoupling product of 4,5-bis(benzylthio)-1,3-dithione-2-thione.

Crystals suitable for single-crystal X-ray diffraction were grown by recrystallisation from ethanol. ¹H-NMR(CDCl₃, 400 MHz) δ/nm: 8.689–8.700(d, 2H); 7.936–7.955(d, 2H), 7.310–7.407(m, 8H).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms. H atoms attached to carbon atoms are omitted for clarity. Symmetry codes: (i) x, y, z; (ii) -x, y + 1/2, -z + 1/2; (iii) -x, -y, -z. (iv) x, -y - 1/2, z - 1/2;
	Fig. 2. Packing diagram of the title compound. H atoms are omitted for clarity.

9-[4,5-Bis(benzylsulfanyl)-1,3-dithiol-2-ylidene]-4,5-diazafluorene top

Crystal data top

C₂₈H₂₀N₂S₄	F(000) = 1064
M_r = 512.70	D_x = 1.399 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3616 reflections
a = 16.5133 (4) Å	θ = 1.3–28.1°
b = 11.4036 (3) Å	µ = 0.41 mm⁻¹
c = 13.1406 (3) Å	T = 296 K
β = 100.246 (1)°	Prism, yellow
V = 2435.06 (10) Å³	0.30 × 0.15 × 0.15 mm
Z = 4

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	4701 independent reflections
Radiation source: fine-focus sealed tube	3365 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 8.192 pixels mm^-1	θ_max = 26.0°, θ_min = 1.3°
Thin–slice ω scans	h = −20→16
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −11→14
T_min = 0.93, T_max = 0.95	l = −16→14
22070 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.088P)² + 0.1086P] where P = (F_o² + 2F_c²)/3
4701 reflections	(Δ/σ)_max < 0.001
307 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₈H₂₀N₂S₄	V = 2435.06 (10) Å³
M_r = 512.70	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.5133 (4) Å	µ = 0.41 mm⁻¹
b = 11.4036 (3) Å	T = 296 K
c = 13.1406 (3) Å	0.30 × 0.15 × 0.15 mm
β = 100.246 (1)°

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	4701 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	3365 reflections with I > 2σ(I)
T_min = 0.93, T_max = 0.95	R_int = 0.028
22070 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.01	Δρ_max = 0.27 e Å⁻³
4701 reflections	Δρ_min = −0.26 e Å⁻³
307 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.26661 (13)	0.3957 (2)	0.12381 (18)	0.0443 (6)
C2	0.11648 (12)	0.37608 (19)	0.01975 (16)	0.0388 (5)
C3	0.22308 (13)	0.3509 (2)	0.19150 (18)	0.0437 (6)
C4	0.40701 (15)	0.3175 (3)	0.0638 (2)	0.0651 (8)
H4A	0.3799	0.2431	0.0702	0.078*
H4B	0.3930	0.3432	−0.0075	0.078*
C5	0.49893 (14)	0.3027 (2)	0.0933 (2)	0.0513 (6)
C6	0.55077 (16)	0.3460 (2)	0.0315 (2)	0.0580 (7)
H6	0.5292	0.3858	−0.0290	0.070*
C7	0.63543 (16)	0.3306 (2)	0.0590 (2)	0.0651 (8)
H7	0.6702	0.3599	0.0167	0.078*
C8	0.66740 (16)	0.2728 (3)	0.1474 (2)	0.0660 (8)
H8	0.7240	0.2628	0.1657	0.079*
C9	0.61659 (17)	0.2296 (2)	0.2091 (2)	0.0652 (8)
H9	0.6387	0.1897	0.2694	0.078*
C10	0.53260 (16)	0.2442 (2)	0.1833 (2)	0.0595 (7)
H10	0.4985	0.2148	0.2263	0.071*
C11	0.04782 (12)	0.37793 (19)	−0.05529 (17)	0.0389 (5)
C12	0.03983 (14)	0.42998 (19)	−0.15886 (17)	0.0415 (5)
C13	0.09229 (15)	0.4942 (2)	−0.20960 (19)	0.0532 (6)
H13	0.1463	0.5095	−0.1782	0.064*
C14	0.06161 (17)	0.5345 (2)	−0.3080 (2)	0.0619 (7)
H14	0.0952	0.5770	−0.3444	0.074*
C15	−0.01918 (17)	0.5114 (2)	−0.35224 (19)	0.0592 (7)
H15	−0.0383	0.5402	−0.4184	0.071*
C16	−0.04129 (13)	0.41232 (19)	−0.21187 (17)	0.0420 (5)
C17	−0.08682 (13)	0.34911 (19)	−0.14401 (17)	0.0426 (6)
C18	−0.03350 (12)	0.32953 (19)	−0.04860 (17)	0.0389 (5)
C19	−0.06498 (13)	0.2702 (2)	0.02749 (18)	0.0454 (6)
H19	−0.0327	0.2552	0.0917	0.054*
C20	−0.14634 (14)	0.2337 (2)	0.0048 (2)	0.0522 (6)
H20	−0.1696	0.1938	0.0543	0.063*
C21	−0.19258 (14)	0.2566 (2)	−0.0910 (2)	0.0554 (7)
H21	−0.2467	0.2299	−0.1041	0.067*
C22	0.27286 (17)	0.4698 (2)	0.37016 (19)	0.0585 (7)
H22A	0.3122	0.5104	0.3361	0.070*
H22B	0.2207	0.5109	0.3541	0.070*
C23	0.30247 (15)	0.4705 (2)	0.48452 (19)	0.0487 (6)
C24	0.38114 (16)	0.5099 (2)	0.5233 (2)	0.0605 (7)
H24	0.4152	0.5329	0.4777	0.073*
C25	0.4097 (2)	0.5156 (3)	0.6274 (3)	0.0802 (9)
H25	0.4626	0.5431	0.6518	0.096*
C26	0.3614 (3)	0.4814 (3)	0.6953 (3)	0.0880 (11)
H26	0.3813	0.4845	0.7661	0.106*
C27	0.2830 (3)	0.4420 (3)	0.6591 (3)	0.0821 (10)
H27	0.2497	0.4193	0.7057	0.099*
C28	0.25280 (17)	0.4359 (2)	0.5533 (2)	0.0623 (7)
H28	0.1997	0.4087	0.5292	0.075*
N1	−0.16515 (11)	0.31450 (18)	−0.16673 (16)	0.0504 (5)
N2	−0.07133 (12)	0.45076 (19)	−0.30653 (15)	0.0525 (5)
S1	0.11858 (3)	0.32501 (5)	0.14525 (4)	0.0451 (2)
S2	0.21191 (3)	0.42865 (6)	0.00076 (5)	0.0470 (2)
S3	0.25999 (4)	0.31922 (6)	0.32190 (5)	0.0541 (2)
S4	0.37216 (4)	0.42555 (6)	0.14861 (5)	0.0535 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0350 (12)	0.0470 (14)	0.0480 (14)	−0.0001 (10)	−0.0005 (11)	−0.0063 (11)
C2	0.0353 (11)	0.0382 (13)	0.0419 (13)	−0.0015 (10)	0.0045 (10)	−0.0024 (10)
C3	0.0407 (12)	0.0413 (13)	0.0454 (14)	0.0020 (10)	−0.0022 (11)	−0.0010 (10)
C4	0.0392 (13)	0.084 (2)	0.0697 (18)	−0.0049 (13)	0.0033 (12)	−0.0222 (15)
C5	0.0391 (12)	0.0519 (15)	0.0618 (17)	−0.0012 (11)	0.0058 (12)	−0.0124 (13)
C6	0.0521 (15)	0.0583 (17)	0.0635 (18)	0.0064 (12)	0.0102 (13)	−0.0009 (13)
C7	0.0462 (15)	0.0671 (19)	0.085 (2)	−0.0009 (13)	0.0201 (15)	−0.0047 (16)
C8	0.0417 (14)	0.0595 (18)	0.093 (2)	0.0095 (13)	0.0005 (15)	−0.0164 (16)
C9	0.0637 (18)	0.0517 (17)	0.0730 (19)	0.0056 (14)	−0.0077 (16)	−0.0025 (14)
C10	0.0593 (17)	0.0562 (17)	0.0620 (18)	−0.0127 (13)	0.0080 (14)	−0.0018 (13)
C11	0.0344 (11)	0.0399 (13)	0.0415 (13)	0.0008 (10)	0.0045 (10)	−0.0010 (10)
C12	0.0409 (12)	0.0427 (13)	0.0399 (13)	0.0018 (10)	0.0043 (10)	−0.0025 (10)
C13	0.0505 (14)	0.0589 (17)	0.0499 (15)	−0.0058 (12)	0.0081 (12)	0.0065 (12)
C14	0.0694 (18)	0.0680 (18)	0.0508 (16)	−0.0089 (14)	0.0175 (14)	0.0094 (14)
C15	0.0690 (17)	0.0673 (18)	0.0394 (15)	0.0036 (14)	0.0048 (13)	0.0064 (13)
C16	0.0389 (12)	0.0458 (14)	0.0393 (13)	0.0022 (10)	0.0019 (10)	−0.0053 (11)
C17	0.0379 (12)	0.0436 (14)	0.0437 (14)	0.0043 (10)	0.0007 (10)	−0.0051 (11)
C18	0.0330 (11)	0.0402 (13)	0.0427 (13)	0.0019 (9)	0.0043 (10)	−0.0050 (10)
C19	0.0391 (13)	0.0488 (14)	0.0479 (14)	−0.0030 (10)	0.0070 (11)	−0.0007 (11)
C20	0.0398 (13)	0.0568 (16)	0.0609 (17)	−0.0034 (11)	0.0114 (12)	0.0008 (13)
C21	0.0341 (13)	0.0568 (16)	0.0738 (19)	−0.0031 (11)	0.0055 (13)	−0.0037 (14)
C22	0.0678 (17)	0.0483 (15)	0.0526 (16)	0.0021 (13)	−0.0080 (13)	−0.0018 (12)
C23	0.0520 (14)	0.0426 (14)	0.0479 (15)	0.0089 (11)	−0.0010 (12)	−0.0001 (11)
C24	0.0580 (16)	0.0592 (17)	0.0609 (18)	−0.0002 (13)	0.0014 (14)	0.0011 (13)
C25	0.085 (2)	0.069 (2)	0.072 (2)	0.0017 (17)	−0.0248 (18)	−0.0088 (17)
C26	0.135 (3)	0.068 (2)	0.051 (2)	0.028 (2)	−0.011 (2)	−0.0131 (16)
C27	0.129 (3)	0.064 (2)	0.061 (2)	0.030 (2)	0.041 (2)	0.0126 (16)
C28	0.0613 (17)	0.0548 (17)	0.072 (2)	0.0086 (13)	0.0143 (15)	0.0028 (14)
N1	0.0345 (10)	0.0572 (13)	0.0560 (13)	−0.0001 (9)	−0.0013 (9)	−0.0045 (10)
N2	0.0558 (13)	0.0602 (14)	0.0388 (12)	0.0043 (10)	0.0011 (10)	−0.0009 (10)
S1	0.0392 (3)	0.0531 (4)	0.0412 (4)	−0.0035 (3)	0.0020 (3)	0.0036 (3)
S2	0.0357 (3)	0.0598 (4)	0.0443 (4)	−0.0074 (3)	0.0040 (3)	0.0001 (3)
S3	0.0621 (4)	0.0465 (4)	0.0470 (4)	−0.0019 (3)	−0.0083 (3)	0.0044 (3)
S4	0.0353 (3)	0.0593 (4)	0.0626 (5)	−0.0048 (3)	−0.0006 (3)	−0.0127 (3)

Geometric parameters (Å, º) top

C1—C3	1.340 (3)	C14—H14	0.9300
C1—S2	1.747 (2)	C15—N2	1.328 (3)
C1—S4	1.749 (2)	C15—H15	0.9300
C2—C11	1.364 (3)	C16—N2	1.329 (3)
C2—S1	1.744 (2)	C16—C17	1.455 (3)
C2—S2	1.745 (2)	C17—N1	1.334 (3)
C3—S1	1.750 (2)	C17—C18	1.416 (3)
C3—S3	1.751 (2)	C18—C19	1.383 (3)
C4—C5	1.508 (3)	C19—C20	1.387 (3)
C4—S4	1.822 (3)	C19—H19	0.9300
C4—H4A	0.9700	C20—C21	1.377 (3)
C4—H4B	0.9700	C20—H20	0.9300
C5—C6	1.372 (3)	C21—N1	1.338 (3)
C5—C10	1.385 (3)	C21—H21	0.9300
C6—C7	1.391 (3)	C22—C23	1.495 (3)
C6—H6	0.9300	C22—S3	1.829 (2)
C7—C8	1.358 (4)	C22—H22A	0.9700
C7—H7	0.9300	C22—H22B	0.9700
C8—C9	1.359 (4)	C23—C28	1.382 (3)
C8—H8	0.9300	C23—C24	1.383 (3)
C9—C10	1.378 (4)	C24—C25	1.367 (4)
C9—H9	0.9300	C24—H24	0.9300
C10—H10	0.9300	C25—C26	1.356 (5)
C11—C18	1.469 (3)	C25—H25	0.9300
C11—C12	1.469 (3)	C26—C27	1.374 (5)
C12—C13	1.392 (3)	C26—H26	0.9300
C12—C16	1.410 (3)	C27—C28	1.392 (4)
C13—C14	1.381 (3)	C27—H27	0.9300
C13—H13	0.9300	C28—H28	0.9300
C14—C15	1.382 (4)

C3—C1—S2	116.50 (17)	N2—C16—C12	125.4 (2)
C3—C1—S4	125.80 (19)	N2—C16—C17	126.1 (2)
S2—C1—S4	117.69 (14)	C12—C16—C17	108.48 (19)
C11—C2—S1	124.27 (16)	N1—C17—C18	125.2 (2)
C11—C2—S2	123.16 (17)	N1—C17—C16	126.5 (2)
S1—C2—S2	112.55 (12)	C18—C17—C16	108.24 (19)
C1—C3—S1	116.50 (18)	C19—C18—C17	117.57 (19)
C1—C3—S3	126.42 (18)	C19—C18—C11	133.8 (2)
S1—C3—S3	117.07 (14)	C17—C18—C11	108.60 (19)
C5—C4—S4	109.37 (17)	C18—C19—C20	117.8 (2)
C5—C4—H4A	109.8	C18—C19—H19	121.1
S4—C4—H4A	109.8	C20—C19—H19	121.1
C5—C4—H4B	109.8	C21—C20—C19	119.9 (2)
S4—C4—H4B	109.8	C21—C20—H20	120.1
H4A—C4—H4B	108.2	C19—C20—H20	120.1
C6—C5—C10	118.7 (2)	N1—C21—C20	124.6 (2)
C6—C5—C4	120.9 (2)	N1—C21—H21	117.7
C10—C5—C4	120.4 (2)	C20—C21—H21	117.7
C5—C6—C7	120.3 (3)	C23—C22—S3	110.54 (17)
C5—C6—H6	119.9	C23—C22—H22A	109.5
C7—C6—H6	119.9	S3—C22—H22A	109.5
C8—C7—C6	120.2 (3)	C23—C22—H22B	109.5
C8—C7—H7	119.9	S3—C22—H22B	109.5
C6—C7—H7	119.9	H22A—C22—H22B	108.1
C7—C8—C9	119.9 (3)	C28—C23—C24	118.7 (2)
C7—C8—H8	120.0	C28—C23—C22	122.0 (2)
C9—C8—H8	120.0	C24—C23—C22	119.3 (2)
C8—C9—C10	120.7 (3)	C25—C24—C23	121.2 (3)
C8—C9—H9	119.7	C25—C24—H24	119.4
C10—C9—H9	119.7	C23—C24—H24	119.4
C9—C10—C5	120.2 (3)	C26—C25—C24	120.4 (3)
C9—C10—H10	119.9	C26—C25—H25	119.8
C5—C10—H10	119.9	C24—C25—H25	119.8
C2—C11—C18	127.0 (2)	C25—C26—C27	119.6 (3)
C2—C11—C12	127.01 (19)	C25—C26—H26	120.2
C18—C11—C12	105.95 (18)	C27—C26—H26	120.2
C13—C12—C16	117.1 (2)	C26—C27—C28	120.7 (3)
C13—C12—C11	134.1 (2)	C26—C27—H27	119.6
C16—C12—C11	108.7 (2)	C28—C27—H27	119.6
C14—C13—C12	117.9 (2)	C23—C28—C27	119.3 (3)
C14—C13—H13	121.1	C23—C28—H28	120.3
C12—C13—H13	121.1	C27—C28—H28	120.3
C13—C14—C15	119.7 (2)	C17—N1—C21	115.0 (2)
C13—C14—H14	120.1	C15—N2—C16	115.5 (2)
C15—C14—H14	120.1	C2—S1—C3	97.15 (10)
N2—C15—C14	124.3 (2)	C2—S2—C1	97.19 (11)
N2—C15—H15	117.8	C3—S3—C22	98.28 (11)
C14—C15—H15	117.8	C1—S4—C4	99.62 (11)

Experimental details

Crystal data
Chemical formula	C₂₈H₂₀N₂S₄
M_r	512.70
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	16.5133 (4), 11.4036 (3), 13.1406 (3)
β (°)	100.246 (1)
V (Å³)	2435.06 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.41
Crystal size (mm)	0.30 × 0.15 × 0.15

Data collection
Diffractometer	Bruker SMART 1K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.93, 0.95
No. of measured, independent and observed [I > 2σ(I)] reflections	22070, 4701, 3365
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.137, 1.01
No. of reflections	4701
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.26

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Acknowledgements

This work was supported by the Major State Basic Research Development Programme and the National Natural Science Foundation of China (grant Nos. 20571029 and 20671038).

References

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