2-Phenyl-3-[6-(3-phenyl­quinoxalin-2-yl)dibenzo[b,d]thio­phen-3-yl]quinoxaline

In the mol­ecule of the title compound, C₄₀H₂₄N₄S, the two benzene rings fused to the thio­phene ring form a dihedral angle of 2.3 (2)°. In the crystal structure, there are no significant hydrogen-bonding inter­actions, but there are π–π stacking inter­actions between mol­ecules.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.059
• wR factor = 0.178
• Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

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) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

2-Phenyl-3-[6-(3-phenylquinoxalin-2-yl)dibenzo[b,d]thiophen-3-yl]quinoxaline

Crystal data

C40H24N4S	Z = 2
Mr = 592.69	F(000) = 616
Triclinic, P1	Dx = 1.401 Mg m^−3 Dm = 1.401 Mg m^−3 Dm measured by not measured
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.9452 (7) Å	Cell parameters from 3810 reflections
b = 11.6962 (9) Å	θ = 2.4–25.1°
c = 12.7037 (9) Å	µ = 0.15 mm^−1
α = 90.480 (3)°	T = 100 K
β = 102.645 (3)°	Prism, colourless
γ = 102.501 (2)°	0.12 × 0.10 × 0.04 mm
V = 1405.27 (18) Å^3

Data collection

Bruker SMART-CCD area-detector diffractometer	4945 independent reflections
Radiation source: fine-focus sealed tube	3300 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.072
φ and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→11
Tmin = 0.982, Tmax = 0.994	k = −13→13
21681 measured reflections	l = −15→15

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)] = 0.059	H-atom parameters not refined
wR(F^2) = 0.179	w = 1/[σ^2(Fo^2) + (0.0656P)^2 + 1.9659P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
4945 reflections	Δρmax = 0.46 e Å^−3
407 parameters	Δρmin = −0.36 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: 0.010 (2)

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	0.21700 (11)	0.50171 (9)	0.90684 (8)	0.0196 (3)
N14	−0.4232 (3)	0.2036 (3)	0.9384 (2)	0.0205 (8)
N19	−0.5487 (3)	0.0331 (3)	0.7658 (3)	0.0209 (8)
N24	0.1765 (3)	0.3151 (3)	1.3924 (2)	0.0193 (8)
N29	0.4381 (3)	0.3182 (3)	1.5333 (3)	0.0191 (8)
C1	0.0472 (4)	0.4122 (3)	0.8836 (3)	0.0183 (9)
C2	0.0209 (4)	0.3497 (3)	0.9738 (3)	0.0155 (9)
C3	−0.1112 (4)	0.2749 (3)	0.9668 (3)	0.0180 (9)
H3	−0.1311	0.2338	1.0278	0.022*
C4	−0.2134 (4)	0.2605 (3)	0.8712 (3)	0.0167 (9)
C5	−0.1852 (4)	0.3245 (3)	0.7824 (3)	0.0201 (9)
H5	−0.2560	0.3148	0.7173	0.024*
C6	−0.0567 (4)	0.4011 (3)	0.7879 (3)	0.0190 (9)
H6	−0.0394	0.4453	0.7280	0.023*
C7	0.2549 (4)	0.4595 (3)	1.0387 (3)	0.0181 (9)
C8	0.1426 (4)	0.3776 (3)	1.0648 (3)	0.0174 (9)
C9	0.1581 (4)	0.3366 (3)	1.1690 (3)	0.0182 (9)
H9	0.0831	0.2808	1.1871	0.022*
C10	0.2837 (4)	0.3776 (3)	1.2463 (3)	0.0167 (9)
C11	0.3928 (4)	0.4602 (3)	1.2175 (3)	0.0203 (9)
H11	0.4777	0.4888	1.2704	0.024*
C12	0.3814 (4)	0.5014 (3)	1.1156 (3)	0.0189 (9)
H12	0.4571	0.5566	1.0978	0.023*
C13	−0.3553 (4)	0.1843 (4)	0.8639 (3)	0.0192 (9)
C15	−0.6401 (4)	0.1631 (4)	0.9996 (3)	0.0243 (10)
H15	−0.5988	0.2194	1.0585	0.029*
C16	−0.7780 (4)	0.1049 (4)	0.9847 (3)	0.0266 (10)
H16	−0.8326	0.1218	1.0331	0.032*
C17	−0.8404 (4)	0.0201 (4)	0.8988 (3)	0.0249 (10)
H17	−0.9361	−0.0207	0.8904	0.030*
C18	−0.7643 (4)	−0.0040 (4)	0.8274 (3)	0.0238 (10)
H18	−0.8073	−0.0608	0.7691	0.029*
C20	−0.4179 (4)	0.0953 (3)	0.7772 (3)	0.0179 (9)
C21	−0.5589 (4)	0.1397 (3)	0.9272 (3)	0.0190 (9)
C22	−0.6217 (4)	0.0554 (3)	0.8400 (3)	0.0190 (9)
C23	0.2947 (4)	0.3384 (3)	1.3582 (3)	0.0178 (9)
C25	0.0612 (4)	0.2562 (3)	1.5370 (3)	0.0208 (9)
H25	−0.0286	0.2455	1.4884	0.025*
C26	0.0687 (4)	0.2385 (3)	1.6436 (3)	0.0220 (10)
H26	−0.0156	0.2148	1.6689	0.026*
C27	0.2014 (4)	0.2553 (3)	1.7168 (3)	0.0232 (10)
H27	0.2060	0.2461	1.7917	0.028*
C28	0.3233 (4)	0.2846 (3)	1.6806 (3)	0.0215 (10)
H28	0.4122	0.2945	1.7301	0.026*
C30	0.4279 (4)	0.3306 (3)	1.4289 (3)	0.0171 (9)
C31	0.1846 (4)	0.2901 (3)	1.4980 (3)	0.0182 (9)
C32	0.3177 (4)	0.3002 (3)	1.5708 (3)	0.0179 (9)
C41	−0.3381 (4)	0.0660 (3)	0.6980 (3)	0.0175 (9)
C42	−0.2323 (4)	0.0042 (4)	0.7287 (3)	0.0223 (10)
H42	−0.2061	−0.0143	0.8020	0.027*
C43	−0.1650 (4)	−0.0303 (4)	0.6543 (3)	0.0252 (10)
H43	−0.0935	−0.0730	0.6761	0.030*
C44	−0.2019 (4)	−0.0026 (4)	0.5472 (3)	0.0237 (10)
H44	−0.1563	−0.0274	0.4956	0.028*
C45	−0.3034 (4)	0.0603 (4)	0.5159 (3)	0.0273 (10)
H45	−0.3272	0.0807	0.4430	0.033*
C46	−0.3715 (4)	0.0944 (4)	0.5915 (3)	0.0232 (10)
H46	−0.4423	0.1379	0.5695	0.028*
C51	0.5579 (4)	0.3330 (3)	1.3890 (3)	0.0170 (9)
C52	0.5531 (4)	0.2647 (3)	1.2981 (3)	0.0197 (9)
H52	0.4660	0.2153	1.2613	0.024*
C53	0.6736 (4)	0.2677 (4)	1.2605 (3)	0.0214 (9)
H53	0.6693	0.2213	1.1976	0.026*
C54	0.8011 (4)	0.3384 (4)	1.3145 (3)	0.0252 (10)
H54	0.8843	0.3401	1.2889	0.030*
C55	0.8074 (4)	0.4060 (4)	1.4050 (3)	0.0261 (10)
H55	0.8949	0.4548	1.4414	0.031*
C56	0.6862 (4)	0.4035 (4)	1.4439 (3)	0.0211 (9)
H56	0.6911	0.4493	1.5073	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.0187 (6)	0.0217 (6)	0.0164 (5)	0.0015 (4)	0.0029 (4)	0.0012 (4)
N14	0.0186 (19)	0.026 (2)	0.0170 (18)	0.0065 (15)	0.0030 (15)	0.0033 (15)
N19	0.0190 (19)	0.0218 (19)	0.0228 (19)	0.0062 (15)	0.0047 (15)	0.0018 (15)
N24	0.0195 (19)	0.0208 (19)	0.0170 (18)	0.0048 (15)	0.0026 (14)	0.0038 (14)
N29	0.0190 (19)	0.0167 (18)	0.0210 (18)	0.0049 (14)	0.0024 (15)	0.0001 (14)
C1	0.018 (2)	0.016 (2)	0.021 (2)	0.0046 (17)	0.0038 (17)	−0.0004 (17)
C2	0.016 (2)	0.016 (2)	0.016 (2)	0.0053 (17)	0.0053 (16)	−0.0009 (16)
C3	0.021 (2)	0.019 (2)	0.016 (2)	0.0054 (17)	0.0061 (17)	0.0000 (16)
C4	0.017 (2)	0.017 (2)	0.018 (2)	0.0073 (17)	0.0039 (17)	−0.0029 (16)
C5	0.021 (2)	0.023 (2)	0.016 (2)	0.0064 (18)	0.0017 (17)	−0.0041 (17)
C6	0.022 (2)	0.020 (2)	0.014 (2)	0.0055 (18)	0.0015 (17)	0.0028 (17)
C7	0.015 (2)	0.019 (2)	0.021 (2)	0.0040 (17)	0.0047 (17)	−0.0042 (17)
C8	0.018 (2)	0.016 (2)	0.018 (2)	0.0034 (17)	0.0050 (17)	−0.0010 (17)
C9	0.016 (2)	0.020 (2)	0.018 (2)	0.0026 (17)	0.0024 (17)	0.0004 (17)
C10	0.016 (2)	0.018 (2)	0.018 (2)	0.0059 (17)	0.0050 (17)	0.0034 (17)
C11	0.020 (2)	0.017 (2)	0.020 (2)	0.0012 (18)	−0.0004 (17)	−0.0037 (17)
C12	0.016 (2)	0.018 (2)	0.022 (2)	0.0013 (17)	0.0042 (17)	0.0016 (17)
C13	0.018 (2)	0.024 (2)	0.015 (2)	0.0058 (18)	0.0002 (17)	0.0018 (17)
C15	0.026 (2)	0.032 (3)	0.017 (2)	0.007 (2)	0.0070 (18)	0.0022 (18)
C16	0.026 (2)	0.035 (3)	0.023 (2)	0.011 (2)	0.0098 (19)	0.007 (2)
C17	0.020 (2)	0.026 (2)	0.030 (2)	0.0056 (19)	0.0074 (19)	0.0071 (19)
C18	0.023 (2)	0.018 (2)	0.028 (2)	0.0022 (18)	0.0031 (19)	−0.0004 (18)
C20	0.017 (2)	0.021 (2)	0.015 (2)	0.0068 (18)	0.0015 (17)	0.0045 (17)
C21	0.016 (2)	0.023 (2)	0.019 (2)	0.0049 (18)	0.0037 (17)	0.0048 (17)
C22	0.018 (2)	0.022 (2)	0.020 (2)	0.0083 (18)	0.0056 (17)	0.0065 (17)
C23	0.017 (2)	0.014 (2)	0.022 (2)	0.0026 (17)	0.0034 (17)	−0.0035 (17)
C25	0.022 (2)	0.018 (2)	0.024 (2)	0.0064 (18)	0.0065 (18)	0.0005 (18)
C26	0.027 (2)	0.016 (2)	0.026 (2)	0.0061 (18)	0.0108 (19)	0.0025 (18)
C27	0.033 (3)	0.017 (2)	0.021 (2)	0.0071 (19)	0.009 (2)	0.0003 (17)
C28	0.027 (2)	0.017 (2)	0.018 (2)	0.0052 (18)	−0.0001 (18)	0.0001 (17)
C30	0.018 (2)	0.014 (2)	0.017 (2)	0.0019 (17)	0.0017 (17)	0.0025 (16)
C31	0.021 (2)	0.013 (2)	0.021 (2)	0.0056 (17)	0.0039 (18)	−0.0003 (17)
C32	0.021 (2)	0.013 (2)	0.021 (2)	0.0049 (17)	0.0070 (18)	0.0013 (16)
C41	0.015 (2)	0.015 (2)	0.019 (2)	−0.0016 (17)	0.0022 (17)	−0.0030 (16)
C42	0.023 (2)	0.025 (2)	0.020 (2)	0.0034 (19)	0.0063 (18)	0.0016 (18)
C43	0.018 (2)	0.025 (2)	0.034 (3)	0.0085 (19)	0.0041 (19)	−0.001 (2)
C44	0.022 (2)	0.022 (2)	0.028 (2)	0.0040 (19)	0.0101 (19)	−0.0033 (19)
C45	0.026 (2)	0.033 (3)	0.020 (2)	0.004 (2)	0.0053 (19)	−0.0003 (19)
C46	0.023 (2)	0.029 (2)	0.020 (2)	0.0112 (19)	0.0031 (18)	0.0008 (18)
C51	0.016 (2)	0.017 (2)	0.018 (2)	0.0060 (17)	0.0018 (17)	0.0054 (17)
C52	0.016 (2)	0.022 (2)	0.020 (2)	0.0038 (17)	0.0018 (17)	−0.0003 (18)
C53	0.026 (2)	0.022 (2)	0.018 (2)	0.0088 (19)	0.0056 (18)	0.0051 (17)
C54	0.017 (2)	0.034 (3)	0.029 (2)	0.011 (2)	0.0073 (19)	0.013 (2)
C55	0.015 (2)	0.025 (2)	0.032 (3)	0.0007 (18)	−0.0046 (19)	0.002 (2)
C56	0.020 (2)	0.021 (2)	0.022 (2)	0.0073 (18)	0.0010 (18)	−0.0021 (17)

Geometric parameters (Å, º)

S—C7	1.735 (4)	C18—C22	1.411 (5)
S—C1	1.745 (4)	C18—H18	0.9500
N14—C13	1.320 (5)	C20—C41	1.490 (5)
N14—C21	1.370 (5)	C21—C22	1.414 (5)
N19—C20	1.323 (5)	C23—C30	1.450 (5)
N19—C22	1.365 (5)	C25—C26	1.360 (5)
N24—C23	1.316 (5)	C25—C31	1.403 (5)
N24—C31	1.364 (5)	C25—H25	0.9500
N29—C30	1.320 (5)	C26—C27	1.412 (6)
N29—C32	1.359 (5)	C26—H26	0.9500
C1—C6	1.396 (5)	C27—C28	1.366 (6)
C1—C2	1.407 (5)	C27—H27	0.9500
C2—C3	1.396 (5)	C28—C32	1.398 (5)
C2—C8	1.456 (5)	C28—H28	0.9500
C3—C4	1.385 (5)	C30—C51	1.483 (5)
C3—H3	0.9500	C31—C32	1.420 (5)
C4—C5	1.404 (5)	C41—C46	1.382 (5)
C4—C13	1.480 (5)	C41—C42	1.392 (6)
C5—C6	1.380 (5)	C42—C43	1.375 (6)
C5—H5	0.9500	C42—H42	0.9500
C6—H6	0.9500	C43—C44	1.390 (6)
C7—C12	1.401 (5)	C43—H43	0.9500
C7—C8	1.406 (5)	C44—C45	1.368 (6)
C8—C9	1.399 (5)	C44—H44	0.9500
C9—C10	1.396 (5)	C45—C46	1.392 (6)
C9—H9	0.9500	C45—H45	0.9500
C10—C11	1.404 (5)	C46—H46	0.9500
C10—C23	1.486 (5)	C51—C52	1.385 (5)
C11—C12	1.375 (5)	C51—C56	1.393 (5)
C11—H11	0.9500	C52—C53	1.378 (5)
C12—H12	0.9500	C52—H52	0.9500
C13—C20	1.444 (5)	C53—C54	1.385 (6)
C15—C16	1.364 (6)	C53—H53	0.9500
C15—C21	1.411 (5)	C54—C55	1.372 (6)
C15—H15	0.9500	C54—H54	0.9500
C16—C17	1.407 (6)	C55—C56	1.394 (6)
C16—H16	0.9500	C55—H55	0.9500
C17—C18	1.365 (6)	C56—H56	0.9500
C17—H17	0.9500
C7—S—C1	91.00 (19)	N19—C22—C21	121.4 (4)
C13—N14—C21	117.3 (3)	C18—C22—C21	119.4 (4)
C20—N19—C22	117.3 (3)	N24—C23—C30	120.9 (3)
C23—N24—C31	117.9 (3)	N24—C23—C10	116.2 (3)
C30—N29—C32	118.2 (3)	C30—C23—C10	122.8 (3)
C6—C1—C2	121.1 (4)	C26—C25—C31	120.7 (4)
C6—C1—S	126.0 (3)	C26—C25—H25	119.7
C2—C1—S	112.9 (3)	C31—C25—H25	119.7
C3—C2—C1	119.1 (3)	C25—C26—C27	120.2 (4)
C3—C2—C8	129.5 (4)	C25—C26—H26	119.9
C1—C2—C8	111.4 (3)	C27—C26—H26	119.9
C4—C3—C2	120.2 (4)	C28—C27—C26	120.3 (4)
C4—C3—H3	119.9	C28—C27—H27	119.8
C2—C3—H3	119.9	C26—C27—H27	119.8
C3—C4—C5	119.7 (4)	C27—C28—C32	120.3 (4)
C3—C4—C13	120.6 (4)	C27—C28—H28	119.9
C5—C4—C13	119.6 (3)	C32—C28—H28	119.9
C6—C5—C4	121.3 (4)	N29—C30—C23	120.8 (4)
C6—C5—H5	119.3	N29—C30—C51	116.4 (3)
C4—C5—H5	119.3	C23—C30—C51	122.8 (3)
C5—C6—C1	118.5 (4)	N24—C31—C25	120.4 (3)
C5—C6—H6	120.7	N24—C31—C32	120.7 (4)
C1—C6—H6	120.7	C25—C31—C32	118.9 (4)
C12—C7—C8	121.1 (4)	N29—C32—C28	120.1 (3)
C12—C7—S	125.7 (3)	N29—C32—C31	120.3 (3)
C8—C7—S	113.3 (3)	C28—C32—C31	119.5 (4)
C9—C8—C7	119.5 (3)	C46—C41—C42	118.4 (4)
C9—C8—C2	129.1 (4)	C46—C41—C20	121.0 (4)
C7—C8—C2	111.4 (3)	C42—C41—C20	120.5 (3)
C10—C9—C8	120.0 (4)	C43—C42—C41	120.8 (4)
C10—C9—H9	120.0	C43—C42—H42	119.6
C8—C9—H9	120.0	C41—C42—H42	119.6
C9—C10—C11	118.9 (3)	C42—C43—C44	119.9 (4)
C9—C10—C23	119.2 (3)	C42—C43—H43	120.0
C11—C10—C23	121.9 (3)	C44—C43—H43	120.0
C12—C11—C10	122.5 (4)	C45—C44—C43	120.2 (4)
C12—C11—H11	118.8	C45—C44—H44	119.9
C10—C11—H11	118.8	C43—C44—H44	119.9
C11—C12—C7	118.1 (4)	C44—C45—C46	119.5 (4)
C11—C12—H12	120.9	C44—C45—H45	120.2
C7—C12—H12	120.9	C46—C45—H45	120.2
N14—C13—C20	121.7 (4)	C41—C46—C45	121.1 (4)
N14—C13—C4	117.0 (3)	C41—C46—H46	119.4
C20—C13—C4	121.2 (3)	C45—C46—H46	119.4
C16—C15—C21	119.9 (4)	C52—C51—C56	119.6 (4)
C16—C15—H15	120.1	C52—C51—C30	120.5 (3)
C21—C15—H15	120.1	C56—C51—C30	119.9 (3)
C15—C16—C17	120.9 (4)	C53—C52—C51	120.5 (4)
C15—C16—H16	119.5	C53—C52—H52	119.7
C17—C16—H16	119.5	C51—C52—H52	119.7
C18—C17—C16	120.4 (4)	C52—C53—C54	119.9 (4)
C18—C17—H17	119.8	C52—C53—H53	120.0
C16—C17—H17	119.8	C54—C53—H53	120.0
C17—C18—C22	120.1 (4)	C55—C54—C53	120.1 (4)
C17—C18—H18	120.0	C55—C54—H54	119.9
C22—C18—H18	120.0	C53—C54—H54	119.9
N19—C20—C13	121.3 (4)	C54—C55—C56	120.5 (4)
N19—C20—C41	116.4 (3)	C54—C55—H55	119.8
C13—C20—C41	122.2 (3)	C56—C55—H55	119.8
N14—C21—C15	119.7 (4)	C51—C56—C55	119.3 (4)
N14—C21—C22	120.8 (4)	C51—C56—H56	120.3
C15—C21—C22	119.4 (4)	C55—C56—H56	120.3
N19—C22—C18	119.2 (4)