2,8-Bis(diphenyl­amino)-5H-5λ⁶-dibenzo[b,d]thio­phene 5,5-dioxide

In the title compound, C₃₆H₂₆N₂O₂S, the two benzene rings fused to the thio­phene ring form a dihedral angle of 8.78 (8)°. In the crystal structure, there are no significant hydrogen-bonding inter­actions or π–π stacking inter­actions between mol­ecules.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.036
• wR factor = 0.092
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); 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).

2,8-Bis(diphenylamino)-5H-5λ⁶-dibenzothiophene 5,5-dioxide

Crystal data

C36H26N2O2S	F(000) = 1152
Mr = 550.65	Dx = 1.321 Mg m^−3 Dm = 1.321 Mg m^−3 Dm measured by not measured
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6419 reflections
a = 9.8988 (2) Å	θ = 2.6–30.9°
b = 19.3898 (4) Å	µ = 0.15 mm^−1
c = 14.4606 (3) Å	T = 100 K
β = 93.866 (1)°	Prism, yellow
V = 2769.19 (10) Å^3	0.3 × 0.22 × 0.18 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	4135 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
Graphite monochromator	θmax = 25.0°, θmin = 1.8°
φ and ω scans	h = −11→11
40230 measured reflections	k = −23→23
4880 independent reflections	l = −17→17

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H-atom parameters not refined
wR(F^2) = 0.092	w = 1/[σ^2(Fo^2) + (0.0394P)^2 + 1.6477P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
4880 reflections	Δρmax = 0.45 e Å^−3
371 parameters	Δρmin = −0.38 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0015 (4)

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.

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 > σ(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 (Ų)

	x	y	z	Uiso*/Ueq
S	0.08629 (4)	0.04027 (2)	0.33982 (3)	0.01946 (13)
O1	0.22095 (13)	0.01588 (6)	0.36180 (9)	0.0288 (3)
O2	−0.02107 (14)	−0.00890 (6)	0.34770 (9)	0.0306 (3)
N1	−0.02189 (14)	0.20280 (7)	−0.00347 (9)	0.0183 (3)
N2	−0.05237 (15)	0.30910 (7)	0.50285 (9)	0.0209 (3)
C1	0.06933 (16)	0.08187 (8)	0.23085 (11)	0.0172 (4)
C2	0.07203 (17)	0.05148 (8)	0.14440 (12)	0.0191 (4)
H2	0.0912	0.0048	0.1387	0.023*
C3	0.04557 (17)	0.09214 (8)	0.06661 (12)	0.0185 (4)
H3	0.0491	0.0728	0.0080	0.022*
C4	0.01338 (16)	0.16235 (8)	0.07535 (11)	0.0163 (3)
C5	0.01513 (16)	0.19232 (8)	0.16349 (11)	0.0163 (3)
H5	−0.0021	0.2392	0.1697	0.020*
C6	0.04261 (16)	0.15183 (8)	0.24132 (11)	0.0157 (3)
C7	0.03456 (16)	0.17245 (8)	0.33921 (11)	0.0165 (3)
C8	0.00458 (17)	0.23689 (8)	0.37311 (11)	0.0177 (4)
H8	−0.0049	0.2745	0.3332	0.021*
C9	−0.01151 (17)	0.24528 (8)	0.46788 (12)	0.0184 (4)
C10	0.00993 (17)	0.18864 (9)	0.52763 (12)	0.0199 (4)
H10	0.0015	0.1944	0.5908	0.024*
C11	0.04332 (17)	0.12458 (9)	0.49418 (11)	0.0197 (4)
H11	0.0582	0.0874	0.5342	0.024*
C12	0.05409 (17)	0.11697 (8)	0.40004 (12)	0.0177 (4)
C21	0.00263 (17)	0.27551 (8)	0.00420 (11)	0.0170 (4)
C22	−0.10385 (18)	0.32209 (9)	−0.00186 (12)	0.0217 (4)
H22	−0.1920	0.3068	−0.0156	0.026*
C23	−0.07813 (19)	0.39145 (9)	0.01269 (13)	0.0258 (4)
H23	−0.1493	0.4228	0.0090	0.031*
C24	0.05324 (19)	0.41448 (9)	0.03277 (12)	0.0240 (4)
H24	0.0698	0.4611	0.0437	0.029*
C25	0.15891 (18)	0.36836 (9)	0.03645 (11)	0.0214 (4)
H25	0.2472	0.3840	0.0485	0.026*
C26	0.13448 (17)	0.29889 (9)	0.02234 (11)	0.0184 (4)
H26	0.2062	0.2678	0.0250	0.022*
C31	−0.10990 (17)	0.17783 (8)	−0.07766 (11)	0.0174 (4)
C32	−0.19903 (17)	0.12332 (8)	−0.06633 (12)	0.0198 (4)
H32	−0.2021	0.1023	−0.0087	0.024*
C33	−0.28279 (18)	0.10033 (9)	−0.14022 (13)	0.0244 (4)
H33	−0.3402	0.0631	−0.1322	0.029*
C34	−0.28237 (19)	0.13188 (10)	−0.22577 (13)	0.0266 (4)
H34	−0.3387	0.1160	−0.2753	0.032*
C35	−0.19675 (18)	0.18754 (10)	−0.23695 (12)	0.0254 (4)
H35	−0.1979	0.2100	−0.2938	0.031*
C36	−0.10998 (18)	0.20980 (9)	−0.16429 (12)	0.0222 (4)
H36	−0.0512	0.2463	−0.1730	0.027*
C41	−0.12611 (18)	0.35766 (9)	0.44389 (12)	0.0212 (4)
C42	−0.23165 (18)	0.33633 (9)	0.38174 (12)	0.0239 (4)
H42	−0.2574	0.2902	0.3797	0.029*
C43	−0.29839 (19)	0.38367 (10)	0.32299 (12)	0.0276 (4)
H43	−0.3675	0.3689	0.2809	0.033*
C44	−0.2628 (2)	0.45249 (10)	0.32671 (13)	0.0315 (5)
H44	−0.3063	0.4840	0.2865	0.038*
C45	−0.1619 (2)	0.47393 (10)	0.39084 (13)	0.0299 (4)
H45	−0.1399	0.5205	0.3953	0.036*
C46	−0.09318 (19)	0.42691 (9)	0.44852 (13)	0.0256 (4)
H46	−0.0244	0.4420	0.4907	0.031*
C51	−0.00805 (17)	0.33003 (9)	0.59487 (11)	0.0203 (4)
C52	0.12459 (18)	0.31901 (9)	0.62939 (12)	0.0226 (4)
H52	0.1855	0.2970	0.5930	0.027*
C53	0.16645 (18)	0.34105 (9)	0.71881 (13)	0.0253 (4)
H53	0.2549	0.3330	0.7422	0.030*
C54	0.0769 (2)	0.37483 (10)	0.77257 (13)	0.0277 (4)
H54	0.1048	0.3900	0.8318	0.033*
C55	−0.05524 (19)	0.38590 (9)	0.73717 (13)	0.0275 (4)
H55	−0.1156	0.4090	0.7729	0.033*
C56	−0.09767 (18)	0.36328 (9)	0.65066 (12)	0.0237 (4)
H56	−0.1871	0.3701	0.6287	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.0249 (2)	0.0142 (2)	0.0184 (2)	−0.00282 (16)	−0.00478 (18)	0.00394 (16)
O1	0.0327 (8)	0.0235 (7)	0.0290 (7)	0.0058 (5)	−0.0080 (6)	0.0014 (5)
O2	0.0396 (8)	0.0254 (7)	0.0257 (7)	−0.0151 (6)	−0.0062 (6)	0.0085 (5)
N1	0.0228 (8)	0.0159 (7)	0.0155 (7)	−0.0019 (6)	−0.0035 (6)	0.0009 (5)
N2	0.0235 (8)	0.0233 (8)	0.0157 (7)	0.0050 (6)	−0.0011 (6)	−0.0002 (6)
C1	0.0140 (8)	0.0173 (8)	0.0198 (9)	−0.0018 (6)	−0.0044 (7)	0.0047 (7)
C2	0.0178 (9)	0.0147 (8)	0.0244 (9)	−0.0008 (6)	−0.0019 (7)	−0.0006 (7)
C3	0.0205 (9)	0.0168 (8)	0.0180 (9)	−0.0016 (7)	−0.0006 (7)	−0.0032 (7)
C4	0.0134 (8)	0.0174 (8)	0.0179 (8)	−0.0017 (6)	−0.0008 (7)	0.0029 (6)
C5	0.0168 (9)	0.0133 (8)	0.0186 (9)	−0.0007 (6)	−0.0001 (7)	0.0007 (6)
C6	0.0129 (8)	0.0163 (8)	0.0175 (8)	−0.0026 (6)	−0.0013 (7)	0.0015 (6)
C7	0.0135 (8)	0.0183 (8)	0.0176 (8)	−0.0027 (6)	−0.0008 (7)	0.0031 (7)
C8	0.0187 (9)	0.0180 (8)	0.0163 (8)	−0.0007 (7)	−0.0002 (7)	0.0049 (7)
C9	0.0149 (9)	0.0217 (9)	0.0186 (9)	−0.0008 (7)	0.0002 (7)	0.0001 (7)
C10	0.0188 (9)	0.0273 (9)	0.0137 (8)	−0.0011 (7)	0.0016 (7)	0.0034 (7)
C11	0.0172 (9)	0.0232 (9)	0.0184 (9)	−0.0016 (7)	−0.0007 (7)	0.0076 (7)
C12	0.0150 (9)	0.0178 (8)	0.0198 (9)	−0.0037 (6)	−0.0018 (7)	0.0035 (7)
C21	0.0231 (9)	0.0159 (8)	0.0116 (8)	−0.0019 (7)	−0.0012 (7)	0.0020 (6)
C22	0.0187 (9)	0.0236 (9)	0.0221 (9)	−0.0015 (7)	−0.0040 (7)	0.0034 (7)
C23	0.0268 (10)	0.0185 (9)	0.0308 (10)	0.0058 (7)	−0.0072 (8)	0.0027 (7)
C24	0.0304 (10)	0.0160 (8)	0.0243 (9)	−0.0037 (7)	−0.0085 (8)	0.0036 (7)
C25	0.0229 (10)	0.0231 (9)	0.0175 (9)	−0.0061 (7)	−0.0038 (7)	0.0030 (7)
C26	0.0188 (9)	0.0219 (9)	0.0144 (8)	0.0018 (7)	−0.0006 (7)	0.0017 (7)
C31	0.0169 (9)	0.0187 (8)	0.0166 (8)	0.0032 (7)	−0.0003 (7)	−0.0028 (7)
C32	0.0218 (9)	0.0178 (8)	0.0197 (9)	0.0027 (7)	0.0019 (7)	−0.0003 (7)
C33	0.0203 (9)	0.0221 (9)	0.0305 (10)	−0.0002 (7)	−0.0004 (8)	−0.0059 (8)
C34	0.0232 (10)	0.0342 (10)	0.0213 (9)	0.0051 (8)	−0.0067 (8)	−0.0096 (8)
C35	0.0255 (10)	0.0365 (11)	0.0141 (9)	0.0045 (8)	−0.0004 (7)	−0.0016 (8)
C36	0.0224 (10)	0.0254 (9)	0.0189 (9)	−0.0002 (7)	0.0013 (7)	0.0005 (7)
C41	0.0216 (9)	0.0266 (9)	0.0156 (8)	0.0054 (7)	0.0022 (7)	0.0010 (7)
C42	0.0214 (10)	0.0286 (10)	0.0218 (9)	−0.0006 (7)	0.0021 (8)	0.0010 (7)
C43	0.0230 (10)	0.0395 (11)	0.0197 (9)	0.0021 (8)	−0.0036 (8)	0.0028 (8)
C44	0.0292 (11)	0.0346 (11)	0.0299 (11)	0.0103 (8)	−0.0024 (9)	0.0078 (8)
C45	0.0346 (11)	0.0218 (9)	0.0324 (11)	0.0051 (8)	−0.0053 (9)	0.0003 (8)
C46	0.0251 (10)	0.0268 (10)	0.0241 (10)	0.0028 (8)	−0.0047 (8)	−0.0020 (7)
C51	0.0233 (10)	0.0208 (9)	0.0166 (9)	−0.0001 (7)	0.0005 (7)	0.0024 (7)
C52	0.0209 (10)	0.0255 (9)	0.0215 (9)	0.0023 (7)	0.0030 (7)	0.0015 (7)
C53	0.0177 (9)	0.0299 (10)	0.0277 (10)	0.0014 (7)	−0.0016 (8)	0.0050 (8)
C54	0.0328 (11)	0.0326 (10)	0.0172 (9)	−0.0040 (8)	−0.0034 (8)	−0.0002 (8)
C55	0.0283 (11)	0.0307 (10)	0.0243 (10)	0.0023 (8)	0.0079 (8)	−0.0035 (8)
C56	0.0161 (9)	0.0295 (10)	0.0253 (10)	0.0029 (7)	0.0001 (7)	0.0017 (7)

Geometric parameters (Å, º)

S—O1	1.4298 (13)	C25—C26	1.381 (2)
S—O2	1.4379 (13)	C25—H25	0.9300
S—C12	1.7632 (17)	C26—H26	0.9300
S—C1	1.7681 (16)	C31—C32	1.393 (2)
N1—C4	1.408 (2)	C31—C36	1.398 (2)
N1—C31	1.421 (2)	C32—C33	1.382 (2)
N1—C21	1.434 (2)	C32—H32	0.9300
N2—C9	1.407 (2)	C33—C34	1.380 (3)
N2—C51	1.432 (2)	C33—H33	0.9300
N2—C41	1.436 (2)	C34—C35	1.388 (3)
C1—C2	1.384 (2)	C34—H34	0.9300
C1—C6	1.392 (2)	C35—C36	1.381 (2)
C2—C3	1.384 (2)	C35—H35	0.9300
C2—H2	0.9300	C36—H36	0.9300
C3—C4	1.406 (2)	C41—C46	1.382 (3)
C3—H3	0.9300	C41—C42	1.394 (2)
C4—C5	1.400 (2)	C42—C43	1.387 (3)
C5—C6	1.384 (2)	C42—H42	0.9300
C5—H5	0.9300	C43—C44	1.380 (3)
C6—C7	1.478 (2)	C43—H43	0.9300
C7—C8	1.382 (2)	C44—C45	1.380 (3)
C7—C12	1.395 (2)	C44—H44	0.9300
C8—C9	1.400 (2)	C45—C46	1.383 (3)
C8—H8	0.9300	C45—H45	0.9300
C9—C10	1.405 (2)	C46—H46	0.9300
C10—C11	1.381 (2)	C51—C52	1.389 (2)
C10—H10	0.9300	C51—C56	1.396 (2)
C11—C12	1.381 (2)	C52—C53	1.398 (3)
C11—H11	0.9300	C52—H52	0.9300
C21—C22	1.386 (2)	C53—C54	1.383 (3)
C21—C26	1.390 (2)	C53—H53	0.9300
C22—C23	1.382 (2)	C54—C55	1.388 (3)
C22—H22	0.9300	C54—H54	0.9300
C23—C24	1.387 (3)	C55—C56	1.365 (3)
C23—H23	0.9300	C55—H55	0.9300
C24—C25	1.374 (3)	C56—H56	0.9300
C24—H24	0.9300
O1—S—O2	116.48 (8)	C24—C25—C26	120.23 (16)
O1—S—C12	111.47 (8)	C24—C25—H25	119.9
O2—S—C12	111.16 (8)	C26—C25—H25	119.9
O1—S—C1	112.34 (8)	C25—C26—C21	119.92 (16)
O2—S—C1	110.29 (7)	C25—C26—H26	120.0
C12—S—C1	92.63 (8)	C21—C26—H26	120.0
C4—N1—C31	121.83 (13)	C32—C31—C36	118.67 (15)
C4—N1—C21	116.98 (13)	C32—C31—N1	122.04 (15)
C31—N1—C21	119.05 (13)	C36—C31—N1	119.27 (15)
C9—N2—C51	120.40 (14)	C33—C32—C31	120.37 (16)
C9—N2—C41	120.69 (14)	C33—C32—H32	119.8
C51—N2—C41	118.53 (14)	C31—C32—H32	119.8
C2—C1—C6	121.90 (15)	C34—C33—C32	120.82 (17)
C2—C1—S	127.18 (13)	C34—C33—H33	119.6
C6—C1—S	110.79 (12)	C32—C33—H33	119.6
C1—C2—C3	118.53 (15)	C33—C34—C35	119.18 (16)
C1—C2—H2	120.7	C33—C34—H34	120.4
C3—C2—H2	120.7	C35—C34—H34	120.4
C2—C3—C4	120.67 (15)	C36—C35—C34	120.51 (17)
C2—C3—H3	119.7	C36—C35—H35	119.7
C4—C3—H3	119.7	C34—C35—H35	119.7
C5—C4—C3	119.66 (15)	C35—C36—C31	120.41 (17)
C5—C4—N1	119.55 (14)	C35—C36—H36	119.8
C3—C4—N1	120.79 (15)	C31—C36—H36	119.8
C6—C5—C4	119.65 (15)	C46—C41—C42	118.90 (16)
C6—C5—H5	120.2	C46—C41—N2	119.96 (16)
C4—C5—H5	120.2	C42—C41—N2	121.14 (16)
C5—C6—C1	119.51 (15)	C43—C42—C41	120.25 (17)
C5—C6—C7	127.23 (15)	C43—C42—H42	119.9
C1—C6—C7	112.99 (14)	C41—C42—H42	119.9
C8—C7—C12	119.85 (15)	C44—C43—C42	120.39 (18)
C8—C7—C6	127.66 (14)	C44—C43—H43	119.8
C12—C7—C6	112.41 (14)	C42—C43—H43	119.8
C7—C8—C9	119.59 (15)	C45—C44—C43	119.25 (17)
C7—C8—H8	120.2	C45—C44—H44	120.4
C9—C8—H8	120.2	C43—C44—H44	120.4
C8—C9—C10	119.27 (15)	C44—C45—C46	120.71 (18)
C8—C9—N2	120.58 (15)	C44—C45—H45	119.6
C10—C9—N2	120.13 (15)	C46—C45—H45	119.6
C11—C10—C9	121.17 (15)	C41—C46—C45	120.41 (17)
C11—C10—H10	119.4	C41—C46—H46	119.8
C9—C10—H10	119.4	C45—C46—H46	119.8
C12—C11—C10	118.54 (15)	C52—C51—C56	119.03 (16)
C12—C11—H11	120.7	C52—C51—N2	120.89 (15)
C10—C11—H11	120.7	C56—C51—N2	120.07 (15)
C11—C12—C7	121.52 (15)	C51—C52—C53	119.95 (16)
C11—C12—S	127.28 (13)	C51—C52—H52	120.0
C7—C12—S	111.16 (12)	C53—C52—H52	120.0
C22—C21—C26	119.97 (15)	C54—C53—C52	120.22 (17)
C22—C21—N1	120.79 (15)	C54—C53—H53	119.9
C26—C21—N1	119.16 (15)	C52—C53—H53	119.9
C23—C22—C21	119.53 (16)	C53—C54—C55	119.32 (17)
C23—C22—H22	120.2	C53—C54—H54	120.3
C21—C22—H22	120.2	C55—C54—H54	120.3
C22—C23—C24	120.37 (16)	C56—C55—C54	120.81 (17)
C22—C23—H23	119.8	C56—C55—H55	119.6
C24—C23—H23	119.8	C54—C55—H55	119.6
C25—C24—C23	119.93 (16)	C55—C56—C51	120.64 (17)
C25—C24—H24	120.0	C55—C56—H56	119.7
C23—C24—H24	120.0	C51—C56—H56	119.7