N-[2-(Benzyl­sulfan­yl)benzyl­idene]-2-(methyl­sulfan­yl)aniline

The title mol­ecule, C₂₁H₁₉NS₂, is non-planar with a dihedral angle between the two benzene rings bonded to the N=CH group of 51.33 (8)°.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C)= 0.004 Å
• R factor = 0.043
• wR factor = 0.149
• Data-to-parameter ratio = 19.1

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

---

Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: DIRDIF99 (Beurskens et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

N-[2-(Benzylsulfanyl)benzylidene]-2-(methylsulfanyl)aniline

Crystal data

C21H19NS2	F(000) = 736
Mr = 349.49	Dx = 1.283 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 9.7960 (7) Å	θ = 5.6–13.7°
b = 17.1416 (16) Å	µ = 0.30 mm^−1
c = 11.2536 (14) Å	T = 297 K
β = 106.699 (8)°	Plate, yellow
V = 1810.0 (3) Å^3	0.50 × 0.50 × 0.23 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.045
non–profiled ω/2θ scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: ψ scan (North et al., 1968)	h = −12→12
Tmin = 0.784, Tmax = 0.931	k = 0→22
4362 measured reflections	l = 0→14
4154 independent reflections	3 standard reflections every 120 min
2629 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.043	w = 1/[σ^2(Fo^2) + (0.0823P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.149	(Δ/σ)max < 0.001
S = 1.10	Δρmax = 0.44 e Å^−3
4154 reflections	Δρmin = −0.32 e Å^−3
217 parameters

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S2	0.14888 (7)	0.01713 (3)	0.32152 (7)	0.0565 (2)
S1	0.31832 (8)	0.37154 (4)	0.14512 (6)	0.0618 (2)
N	0.14846 (19)	0.26240 (10)	0.24171 (18)	0.0441 (4)
C16	0.0200 (2)	0.05986 (12)	0.1948 (2)	0.0431 (5)
C2	0.3342 (2)	0.36076 (11)	0.3037 (2)	0.0418 (5)
C21	0.1808 (3)	−0.11917 (13)	0.4433 (2)	0.0496 (6)
C15	−0.0849 (2)	0.01618 (13)	0.1119 (2)	0.0525 (6)
H15	−0.092	−0.037	0.1254	0.063*
C12	−0.0689 (2)	0.17371 (13)	0.0705 (2)	0.0505 (6)
H12	−0.0642	0.2269	0.0558	0.061*
C6	0.2453 (3)	0.30037 (13)	0.4611 (2)	0.0497 (6)
H6	0.1816	0.267	0.4829	0.06*
C10	0.1288 (2)	0.19093 (12)	0.2632 (2)	0.0437 (5)
H10	0.1813	0.1695	0.3383	0.052*
C7	0.2429 (2)	0.30657 (11)	0.3375 (2)	0.0403 (5)
C14	−0.1782 (3)	0.05059 (15)	0.0106 (3)	0.0579 (7)
H14	−0.2472	0.0204	−0.0441	0.069*
C3	0.4314 (3)	0.40135 (12)	0.3971 (2)	0.0511 (6)
H3	0.4947	0.4356	0.3766	0.061*
C11	0.0273 (2)	0.14123 (12)	0.1747 (2)	0.0417 (5)
C20	0.0813 (3)	−0.08046 (13)	0.3328 (3)	0.0564 (6)
H20A	−0.0138	−0.0777	0.3426	0.068*
H20B	0.0769	−0.1099	0.2582	0.068*
C24	0.3673 (3)	−0.19226 (17)	0.6466 (3)	0.0698 (8)
H24	0.4298	−0.2164	0.7147	0.084*
C5	0.3409 (3)	0.34295 (14)	0.5519 (2)	0.0573 (6)
H5	0.3411	0.3385	0.6344	0.069*
C22	0.3023 (3)	−0.15707 (14)	0.4328 (3)	0.0587 (6)
H22	0.3218	−0.1581	0.3566	0.07*
C23	0.3946 (3)	−0.19324 (16)	0.5342 (3)	0.0698 (8)
H23	0.4756	−0.2183	0.526	0.084*
C26	0.1560 (3)	−0.11897 (15)	0.5572 (3)	0.0622 (7)
H26	0.0757	−0.0936	0.5665	0.075*
C13	−0.1707 (3)	0.12955 (15)	−0.0113 (2)	0.0574 (6)
H13	−0.2337	0.1525	−0.0805	0.069*
C4	0.4361 (3)	0.39206 (14)	0.5200 (3)	0.0571 (6)
H4	0.5036	0.419	0.5814	0.068*
C25	0.2475 (4)	−0.15565 (18)	0.6587 (3)	0.0708 (8)
H25	0.2279	−0.1555	0.7348	0.085*
C1	0.4201 (3)	0.45838 (16)	0.1414 (3)	0.0695 (8)
H1A	0.4177	0.4697	0.0573	0.104*
H1B	0.517	0.4505	0.1903	0.104*
H1C	0.3799	0.5013	0.1747	0.104*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S2	0.0508 (4)	0.0326 (3)	0.0746 (4)	−0.0057 (2)	−0.0001 (3)	0.0057 (3)
S1	0.0752 (5)	0.0533 (4)	0.0602 (4)	−0.0213 (3)	0.0247 (3)	−0.0034 (3)
N	0.0410 (10)	0.0313 (9)	0.0595 (12)	−0.0054 (7)	0.0138 (8)	0.0011 (8)
C16	0.0356 (11)	0.0328 (10)	0.0610 (14)	−0.0006 (8)	0.0142 (10)	0.0007 (9)
C2	0.0393 (11)	0.0263 (9)	0.0601 (13)	0.0011 (8)	0.0150 (10)	0.0010 (9)
C21	0.0507 (13)	0.0303 (10)	0.0693 (16)	−0.0037 (9)	0.0195 (12)	0.0019 (10)
C15	0.0432 (12)	0.0368 (11)	0.0726 (17)	−0.0034 (10)	0.0087 (11)	−0.0022 (11)
C12	0.0459 (12)	0.0387 (12)	0.0673 (15)	−0.0012 (10)	0.0167 (11)	0.0051 (11)
C6	0.0501 (13)	0.0378 (11)	0.0654 (16)	0.0009 (10)	0.0233 (12)	0.0027 (10)
C10	0.0396 (11)	0.0336 (10)	0.0583 (13)	−0.0001 (9)	0.0147 (10)	0.0022 (10)
C7	0.0364 (10)	0.0286 (9)	0.0564 (13)	0.0043 (8)	0.0144 (9)	0.0021 (9)
C14	0.0424 (12)	0.0498 (13)	0.0740 (17)	−0.0058 (11)	0.0047 (12)	−0.0083 (12)
C3	0.0448 (12)	0.0369 (11)	0.0701 (17)	−0.0080 (10)	0.0140 (11)	−0.0026 (11)
C11	0.0369 (10)	0.0325 (10)	0.0578 (13)	−0.0017 (8)	0.0172 (10)	0.0007 (9)
C20	0.0561 (14)	0.0339 (11)	0.0752 (17)	−0.0066 (10)	0.0125 (12)	0.0061 (11)
C24	0.0664 (17)	0.0590 (16)	0.076 (2)	−0.0015 (14)	0.0076 (15)	0.0118 (14)
C5	0.0684 (16)	0.0494 (13)	0.0539 (14)	0.0055 (12)	0.0170 (12)	−0.0007 (11)
C22	0.0644 (16)	0.0463 (13)	0.0726 (17)	0.0049 (12)	0.0309 (14)	0.0053 (12)
C23	0.0560 (16)	0.0564 (15)	0.099 (2)	0.0142 (13)	0.0253 (16)	0.0109 (15)
C26	0.0609 (16)	0.0543 (15)	0.0788 (19)	0.0025 (12)	0.0320 (14)	−0.0016 (14)
C13	0.0470 (13)	0.0541 (14)	0.0644 (16)	0.0026 (11)	0.0051 (12)	0.0053 (12)
C4	0.0573 (15)	0.0440 (13)	0.0629 (17)	−0.0027 (11)	0.0060 (12)	−0.0071 (11)
C25	0.084 (2)	0.0702 (18)	0.0636 (17)	−0.0055 (16)	0.0291 (15)	0.0038 (15)
C1	0.0712 (18)	0.0582 (16)	0.0815 (19)	−0.0123 (14)	0.0258 (15)	0.0182 (14)

Geometric parameters (Å, º)

S2—C16	1.769 (2)	C14—C13	1.381 (3)
S2—C20	1.817 (2)	C14—H14	0.93
S1—C2	1.756 (2)	C3—C4	1.380 (4)
S1—C1	1.799 (3)	C3—H3	0.93
N—C10	1.274 (3)	C20—H20A	0.97
N—C7	1.420 (3)	C20—H20B	0.97
C16—C15	1.391 (3)	C24—C23	1.365 (4)
C16—C11	1.418 (3)	C24—C25	1.371 (4)
C2—C3	1.386 (3)	C24—H24	0.93
C2—C7	1.415 (3)	C5—C4	1.378 (4)
C21—C26	1.372 (4)	C5—H5	0.93
C21—C22	1.391 (3)	C22—C23	1.383 (4)
C21—C20	1.496 (3)	C22—H22	0.93
C15—C14	1.373 (3)	C23—H23	0.93
C15—H15	0.93	C26—C25	1.384 (4)
C12—C13	1.374 (3)	C26—H26	0.93
C12—C11	1.393 (3)	C13—H13	0.93
C12—H12	0.93	C4—H4	0.93
C6—C5	1.380 (3)	C25—H25	0.93
C6—C7	1.388 (3)	C1—H1A	0.96
C6—H6	0.93	C1—H1B	0.96
C10—C11	1.462 (3)	C1—H1C	0.96
C10—H10	0.93
C16—S2—C20	104.34 (11)	C21—C20—S2	107.65 (16)
C2—S1—C1	102.87 (13)	C21—C20—H20A	110.2
C10—N—C7	118.00 (19)	S2—C20—H20A	110.2
C15—C16—C11	119.0 (2)	C21—C20—H20B	110.2
C15—C16—S2	122.42 (17)	S2—C20—H20B	110.2
C11—C16—S2	118.58 (16)	H20A—C20—H20B	108.5
C3—C2—C7	118.4 (2)	C23—C24—C25	119.9 (3)
C3—C2—S1	123.98 (18)	C23—C24—H24	120
C7—C2—S1	117.63 (17)	C25—C24—H24	120
C26—C21—C22	117.8 (2)	C4—C5—C6	119.7 (2)
C26—C21—C20	121.8 (2)	C4—C5—H5	120.1
C22—C21—C20	120.4 (2)	C6—C5—H5	120.1
C14—C15—C16	120.8 (2)	C23—C22—C21	120.8 (3)
C14—C15—H15	119.6	C23—C22—H22	119.6
C16—C15—H15	119.6	C21—C22—H22	119.6
C13—C12—C11	122.0 (2)	C24—C23—C22	120.2 (3)
C13—C12—H12	119	C24—C23—H23	119.9
C11—C12—H12	119	C22—C23—H23	119.9
C5—C6—C7	121.0 (2)	C21—C26—C25	121.5 (3)
C5—C6—H6	119.5	C21—C26—H26	119.2
C7—C6—H6	119.5	C25—C26—H26	119.2
N—C10—C11	122.8 (2)	C12—C13—C14	119.1 (2)
N—C10—H10	118.6	C12—C13—H13	120.5
C11—C10—H10	118.6	C14—C13—H13	120.5
C6—C7—C2	119.3 (2)	C5—C4—C3	120.1 (2)
C6—C7—N	122.7 (2)	C5—C4—H4	119.9
C2—C7—N	118.0 (2)	C3—C4—H4	119.9
C15—C14—C13	120.8 (2)	C24—C25—C26	119.7 (3)
C15—C14—H14	119.6	C24—C25—H25	120.1
C13—C14—H14	119.6	C26—C25—H25	120.1
C4—C3—C2	121.3 (2)	S1—C1—H1A	109.5
C4—C3—H3	119.3	S1—C1—H1B	109.5
C2—C3—H3	119.3	H1A—C1—H1B	109.5
C12—C11—C16	118.3 (2)	S1—C1—H1C	109.5
C12—C11—C10	120.27 (19)	H1A—C1—H1C	109.5
C16—C11—C10	121.4 (2)	H1B—C1—H1C	109.5
C20—S2—C16—C15	−13.5 (2)	S2—C16—C11—C12	176.09 (17)
C20—S2—C16—C11	168.75 (19)	C15—C16—C11—C10	175.7 (2)
C1—S1—C2—C3	−13.2 (2)	S2—C16—C11—C10	−6.5 (3)
C1—S1—C2—C7	167.53 (18)	N—C10—C11—C12	−10.2 (3)
C11—C16—C15—C14	1.5 (4)	N—C10—C11—C16	172.4 (2)
S2—C16—C15—C14	−176.2 (2)	C26—C21—C20—S2	94.9 (3)
C7—N—C10—C11	175.94 (19)	C22—C21—C20—S2	−85.3 (2)
C5—C6—C7—C2	−3.7 (3)	C16—S2—C20—C21	−176.76 (18)
C5—C6—C7—N	178.5 (2)	C7—C6—C5—C4	−0.4 (4)
C3—C2—C7—C6	5.1 (3)	C26—C21—C22—C23	0.0 (4)
S1—C2—C7—C6	−175.54 (16)	C20—C21—C22—C23	−179.8 (2)
C3—C2—C7—N	−176.94 (18)	C25—C24—C23—C22	0.3 (4)
S1—C2—C7—N	2.4 (3)	C21—C22—C23—C24	0.1 (4)
C10—N—C7—C6	−41.5 (3)	C22—C21—C26—C25	−0.5 (4)
C10—N—C7—C2	140.7 (2)	C20—C21—C26—C25	179.3 (2)
C16—C15—C14—C13	−0.4 (4)	C11—C12—C13—C14	0.2 (4)
C7—C2—C3—C4	−2.6 (3)	C15—C14—C13—C12	−0.4 (4)
S1—C2—C3—C4	178.10 (19)	C6—C5—C4—C3	3.0 (4)
C13—C12—C11—C16	0.9 (3)	C2—C3—C4—C5	−1.5 (4)
C13—C12—C11—C10	−176.6 (2)	C23—C24—C25—C26	−0.9 (4)
C15—C16—C11—C12	−1.7 (3)	C21—C26—C25—C24	1.0 (4)