9-[4,5-Bis(benzyl-sulfan-yl)-1,3-dithiol-2-yl-idene]-4,5-diaza-fluorene.

In rhe title compound, C(28)H(20)N(2)S(4), the 1,3-dithiol-2-yl-idene and 4,5-diaza-fluoren-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-yl-idene 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 = 512.70

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.137

S = 1.00

4701 reflections

307 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C28H20N2S4	F000 = 1064
Mr = 512.70	Dx = 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 = 1.3–28.1º
b = 11.4036 (3) Å	µ = 0.41 mm−1
c = 13.1406 (3) Å	T = 296 (2) K
β = 100.2460 (10)º	Prism, yellow
V = 2435.06 (10) Å3	0.30 × 0.15 × 0.15 mm
Z = 4

Bruker SMART 1K CCD area-detector diffractometer	4701 independent reflections
Radiation source: fine-focus sealed tube	3365 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.028
Detector resolution: 8.192 pixels mm-1	θmax = 26.0º
T = 296(2) K	θmin = 1.3º
Thin–slice ω scans	h = −20→16
Absorption correction: multi-scan(SADABS; Bruker, 2000)	k = −11→14
Tmin = 0.93, Tmax = 0.95	l = −16→14
22070 measured reflections

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)] = 0.039	H-atom parameters constrained
wR(F2) = 0.137	w = 1/[σ2(Fo2) + (0.088P)2 + 0.1086P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
4701 reflections	Δρmax = 0.27 e Å−3
307 parameters	Δρmin = −0.25 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

	x	y	z	Uiso*/Ueq
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)

	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)

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)