2,2,3,3'-Tetra-phenyl-7,7'-biquinoxaline.

In the crystal structure of the title compound, C(40)H(26)N(4), mol-ecules reside on crystallographic centers of inversion and are linked via C-H⋯N inter-actions about inversion centers into one-dimensional chains: longer C-H⋯π(arene) inter-actions complete the inter-molecular inter-actions.

Related literature

For the synthesis of quinoxalines, see: Kowalski et al. (2006 ▶); Kou et al. (2006 ▶); Baek & Tan (2006 ▶). For applications of quinoxalines see: Mollegaard et al. (2000 ▶); Aldakov et al. (2005 ▶); Kaiwar et al. (1997 ▶); Anzenbacher et al. (2000 ▶). For related literature, see: Brown et al. (2004 ▶); Bruno et al. (2002 ▶); Gibson et al. (2006 ▶); Page et al. (1998 ▶); Pascal & Ho (1993 ▶); Salvatore et al. (2006 ▶); Simpson & Gordon (1995 ▶); Willett et al. (2001 ▶); Wozniak et al. (1993 ▶); Wu et al. (2002 ▶).

Experimental

Crystal data

C40H26N4

M = 562.65

Triclinic,

a = 5.70240 (10) Å

b = 9.9534 (2) Å

c = 12.9785 (3) Å

α = 105.3520 (10)°

β = 96.6170 (10)°

γ = 91.7510 (10)°

V = 704.19 (3) Å3

Z = 1

Cu Kα radiation

μ = 0.61 mm−1

T = 100 (2) K

0.19 × 0.12 × 0.06 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: numerical (SADABS; Sheldrick, 2004 ▶) T min = 0.893, T max = 0.964

12179 measured reflections

2429 independent reflections

2156 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.091

S = 1.06

2429 reflections

251 parameters

All H-atom parameters refined

Δρmax = 0.23 e Å−3

Δρmin = −0.18 e Å−3

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

Crystal structure: contains datablocks I, global, publication_text. DOI: 10.1107/S1600536807033521/gg2021sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807033521/gg2021Isup2.hkl

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

C40H26N4	Z = 1
Mr = 562.65	F000 = 294
Triclinic, P1	Dx = 1.327 Mg m−3
Hall symbol: -P 1	Cu Kα radiation λ = 1.54178 Å
a = 5.70240 (10) Å	Cell parameters from 585 reflections
b = 9.9534 (2) Å	θ = 3.6–67.0º
c = 12.9785 (3) Å	µ = 0.61 mm−1
α = 105.3520 (10)º	T = 100 (2) K
β = 96.6170 (10)º	Block, colourless
γ = 91.7510 (10)º	0.19 × 0.12 × 0.06 mm
V = 704.19 (3) Å3

Bruker SMART APEXII CCD diffractometer	2429 independent reflections
Radiation source: fine-focus sealed tube	2156 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.033
T = 100(2) K	θmax = 67.0º
ω and ψ scans	θmin = 3.6º
Absorption correction: numerical(SADABS; Sheldrick, 2004)	h = −6→6
Tmin = 0.893, Tmax = 0.964	k = −11→11
12179 measured reflections	l = −15→15

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)] = 0.033	All H-atom parameters refined
wR(F2) = 0.091	w = 1/[σ2(Fo2) + (0.0496P)2 + 0.1323P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2429 reflections	Δρmax = 0.23 e Å−3
251 parameters	Δρmin = −0.18 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
N1	0.51854 (16)	0.85128 (10)	0.69940 (8)	0.0221 (2)
N2	0.23046 (17)	0.60236 (10)	0.64109 (8)	0.0224 (2)
C1	0.03603 (19)	0.94087 (11)	0.52202 (9)	0.0209 (3)
C2	0.2496 (2)	0.94755 (12)	0.58600 (9)	0.0226 (3)
C3	0.31629 (19)	0.83612 (11)	0.62942 (9)	0.0211 (3)
C4	0.57593 (19)	0.74558 (12)	0.73939 (9)	0.0212 (3)
C5	0.43238 (19)	0.61520 (12)	0.70434 (9)	0.0211 (3)
C6	0.1661 (2)	0.71321 (12)	0.60385 (9)	0.0217 (3)
C7	−0.0511 (2)	0.70597 (12)	0.53726 (9)	0.0231 (3)
C8	−0.1142 (2)	0.81609 (12)	0.49890 (9)	0.0225 (3)
C9	0.79004 (19)	0.77207 (11)	0.82117 (9)	0.0219 (3)
C10	0.9637 (2)	0.87320 (12)	0.81830 (10)	0.0239 (3)
C11	1.1675 (2)	0.90121 (13)	0.89186 (10)	0.0269 (3)
C12	1.2013 (2)	0.82934 (13)	0.97005 (10)	0.0288 (3)
C13	1.0272 (2)	0.73173 (13)	0.97578 (10)	0.0281 (3)
C14	0.8232 (2)	0.70364 (12)	0.90232 (10)	0.0252 (3)
C15	0.49998 (19)	0.48375 (11)	0.73197 (9)	0.0215 (3)
C16	0.7014 (2)	0.41920 (12)	0.69865 (9)	0.0240 (3)
C17	0.7507 (2)	0.29096 (12)	0.71734 (10)	0.0248 (3)
C18	0.6025 (2)	0.22840 (12)	0.77110 (9)	0.0244 (3)
C19	0.4035 (2)	0.29355 (13)	0.80581 (10)	0.0268 (3)
C20	0.3503 (2)	0.42037 (12)	0.78536 (10)	0.0247 (3)
H2	0.361 (3)	1.0290 (16)	0.6039 (12)	0.035 (4)*
H7	−0.153 (3)	0.6200 (16)	0.5199 (12)	0.035 (4)*
H8	−0.267 (2)	0.8096 (13)	0.4535 (11)	0.021 (3)*
H10	0.938 (2)	0.9233 (14)	0.7633 (11)	0.026 (3)*
H11	1.287 (3)	0.9694 (15)	0.8870 (12)	0.033 (4)*
H12	1.344 (3)	0.8484 (16)	1.0224 (12)	0.036 (4)*
H13	1.048 (2)	0.6786 (16)	1.0312 (13)	0.037 (4)*
H14	0.698 (3)	0.6366 (16)	0.9090 (12)	0.033 (4)*
H16	0.807 (2)	0.4646 (15)	0.6621 (12)	0.029 (3)*
H17	0.888 (2)	0.2451 (14)	0.6924 (11)	0.023 (3)*
H18	0.640 (2)	0.1387 (15)	0.7834 (11)	0.028 (3)*
H19	0.296 (2)	0.2499 (15)	0.8440 (12)	0.033 (4)*
H20	0.210 (3)	0.4660 (15)	0.8084 (12)	0.032 (4)*

	U11	U22	U33	U12	U13	U23
N1	0.0212 (5)	0.0209 (5)	0.0245 (5)	0.0010 (4)	0.0015 (4)	0.0073 (4)
N2	0.0241 (5)	0.0195 (5)	0.0240 (5)	0.0010 (4)	0.0019 (4)	0.0070 (4)
C1	0.0227 (6)	0.0196 (6)	0.0205 (6)	0.0010 (5)	0.0037 (4)	0.0052 (4)
C2	0.0228 (6)	0.0193 (6)	0.0258 (6)	−0.0015 (5)	0.0015 (4)	0.0073 (5)
C3	0.0204 (6)	0.0208 (6)	0.0216 (6)	0.0006 (5)	0.0027 (4)	0.0049 (4)
C4	0.0219 (6)	0.0196 (5)	0.0231 (6)	0.0019 (4)	0.0047 (4)	0.0067 (4)
C5	0.0204 (5)	0.0208 (6)	0.0224 (6)	0.0010 (4)	0.0035 (4)	0.0060 (4)
C6	0.0243 (6)	0.0189 (5)	0.0217 (6)	0.0012 (5)	0.0038 (4)	0.0051 (4)
C7	0.0238 (6)	0.0199 (6)	0.0244 (6)	−0.0024 (5)	0.0005 (4)	0.0053 (4)
C8	0.0224 (6)	0.0217 (6)	0.0227 (6)	−0.0013 (5)	0.0003 (4)	0.0058 (4)
C9	0.0207 (6)	0.0187 (5)	0.0249 (6)	0.0033 (4)	0.0025 (4)	0.0034 (4)
C10	0.0247 (6)	0.0207 (6)	0.0260 (6)	0.0034 (5)	0.0037 (5)	0.0057 (5)
C11	0.0227 (6)	0.0256 (6)	0.0302 (7)	−0.0002 (5)	0.0041 (5)	0.0036 (5)
C12	0.0224 (6)	0.0343 (7)	0.0261 (6)	0.0014 (5)	−0.0025 (5)	0.0042 (5)
C13	0.0279 (6)	0.0295 (6)	0.0270 (6)	0.0038 (5)	0.0002 (5)	0.0087 (5)
C14	0.0248 (6)	0.0235 (6)	0.0262 (6)	0.0008 (5)	0.0015 (5)	0.0058 (5)
C15	0.0218 (6)	0.0185 (5)	0.0225 (6)	−0.0011 (4)	−0.0023 (4)	0.0050 (4)
C16	0.0240 (6)	0.0229 (6)	0.0258 (6)	0.0002 (5)	0.0034 (5)	0.0077 (5)
C17	0.0238 (6)	0.0225 (6)	0.0264 (6)	0.0041 (5)	0.0008 (5)	0.0045 (5)
C18	0.0285 (6)	0.0180 (5)	0.0253 (6)	0.0009 (5)	−0.0048 (5)	0.0069 (4)
C19	0.0260 (6)	0.0259 (6)	0.0310 (7)	−0.0011 (5)	0.0017 (5)	0.0131 (5)
C20	0.0206 (6)	0.0248 (6)	0.0296 (6)	0.0023 (5)	0.0030 (5)	0.0089 (5)

N1—C4	1.3245 (15)	C10—H10	0.974 (14)
N1—C3	1.3613 (14)	C11—C12	1.3880 (18)
N2—C5	1.3166 (15)	C11—H11	0.966 (15)
N2—C6	1.3609 (15)	C12—C13	1.3899 (18)
C1—C2	1.3819 (16)	C12—H12	0.978 (15)
C1—C8	1.4301 (16)	C13—C14	1.3870 (17)
C1—C1i	1.488 (2)	C13—H13	0.998 (15)
C2—C3	1.4141 (16)	C14—H14	0.988 (15)
C2—H2	0.976 (15)	C15—C16	1.3898 (17)
C3—C6	1.4129 (16)	C15—C20	1.3936 (16)
C4—C5	1.4484 (16)	C16—C17	1.3918 (16)
C4—C9	1.4900 (15)	C16—H16	0.976 (14)
C5—C15	1.4955 (15)	C17—C18	1.3865 (17)
C6—C7	1.4143 (16)	C17—H17	0.962 (14)
C7—C8	1.3604 (16)	C18—C19	1.3852 (18)
C7—H7	0.977 (15)	C18—H18	0.973 (14)
C8—H8	0.986 (13)	C19—C20	1.3922 (16)
C9—C14	1.3967 (17)	C19—H19	0.990 (15)
C9—C10	1.4010 (16)	C20—H20	0.971 (15)
C10—C11	1.3868 (17)
C4—N1—C3	118.29 (10)	C9—C10—H10	118.5 (8)
C5—N2—C6	117.97 (10)	C12—C11—C10	120.12 (11)
C2—C1—C8	117.90 (10)	C12—C11—H11	120.4 (8)
C2—C1—C1i	121.33 (13)	C10—C11—H11	119.4 (8)
C8—C1—C1i	120.76 (12)	C11—C12—C13	119.59 (11)
C1—C2—C3	121.34 (11)	C11—C12—H12	120.8 (9)
C1—C2—H2	122.0 (8)	C13—C12—H12	119.6 (9)
C3—C2—H2	116.6 (9)	C14—C13—C12	120.35 (11)
N1—C3—C6	120.83 (10)	C14—C13—H13	118.8 (9)
N1—C3—C2	119.57 (10)	C12—C13—H13	120.9 (9)
C6—C3—C2	119.52 (10)	C13—C14—C9	120.67 (11)
N1—C4—C5	120.22 (10)	C13—C14—H14	119.5 (8)
N1—C4—C9	115.70 (10)	C9—C14—H14	119.8 (8)
C5—C4—C9	124.07 (10)	C16—C15—C20	119.65 (10)
N2—C5—C4	121.55 (10)	C16—C15—C5	120.82 (10)
N2—C5—C15	114.09 (10)	C20—C15—C5	119.38 (10)
C4—C5—C15	124.33 (10)	C15—C16—C17	119.93 (11)
N2—C6—C3	120.68 (10)	C15—C16—H16	119.3 (8)
N2—C6—C7	120.32 (10)	C17—C16—H16	120.8 (8)
C3—C6—C7	118.99 (10)	C18—C17—C16	120.38 (11)
C8—C7—C6	120.36 (11)	C18—C17—H17	119.8 (8)
C8—C7—H7	121.6 (9)	C16—C17—H17	119.8 (8)
C6—C7—H7	118.1 (9)	C19—C18—C17	119.78 (11)
C7—C8—C1	121.85 (11)	C19—C18—H18	121.0 (8)
C7—C8—H8	119.2 (7)	C17—C18—H18	119.2 (8)
C1—C8—H8	119.0 (7)	C18—C19—C20	120.18 (11)
C14—C9—C10	118.36 (11)	C18—C19—H19	120.6 (8)
C14—C9—C4	123.20 (10)	C20—C19—H19	119.2 (8)
C10—C9—C4	118.42 (10)	C15—C20—C19	120.05 (11)
C11—C10—C9	120.85 (11)	C15—C20—H20	119.3 (8)
C11—C10—H10	120.7 (8)	C19—C20—H20	120.7 (8)
C8—C1—C2—C3	−1.34 (17)	N1—C4—C9—C14	152.27 (11)
C1i—C1—C2—C3	178.88 (12)	C5—C4—C9—C14	−26.95 (17)
C4—N1—C3—C6	2.79 (16)	N1—C4—C9—C10	−25.98 (15)
C4—N1—C3—C2	179.56 (10)	C5—C4—C9—C10	154.81 (11)
C1—C2—C3—N1	−174.44 (10)	C14—C9—C10—C11	2.26 (17)
C1—C2—C3—C6	2.37 (17)	C4—C9—C10—C11	−179.41 (10)
C3—N1—C4—C5	3.29 (16)	C9—C10—C11—C12	−0.35 (18)
C3—N1—C4—C9	−175.95 (9)	C10—C11—C12—C13	−1.57 (19)
C6—N2—C5—C4	3.88 (16)	C11—C12—C13—C14	1.55 (19)
C6—N2—C5—C15	−174.05 (9)	C12—C13—C14—C9	0.41 (18)
N1—C4—C5—N2	−6.97 (17)	C10—C9—C14—C13	−2.28 (17)
C9—C4—C5—N2	172.21 (10)	C4—C9—C14—C13	179.47 (10)
N1—C4—C5—C15	170.75 (10)	N2—C5—C15—C16	115.78 (12)
C9—C4—C5—C15	−10.07 (17)	C4—C5—C15—C16	−62.09 (15)
C5—N2—C6—C3	2.27 (16)	N2—C5—C15—C20	−59.79 (14)
C5—N2—C6—C7	−178.84 (10)	C4—C5—C15—C20	122.33 (12)
N1—C3—C6—N2	−5.86 (17)	C20—C15—C16—C17	0.92 (17)
C2—C3—C6—N2	177.37 (10)	C5—C15—C16—C17	−174.64 (10)
N1—C3—C6—C7	175.23 (10)	C15—C16—C17—C18	−1.36 (18)
C2—C3—C6—C7	−1.54 (16)	C16—C17—C18—C19	0.39 (17)
N2—C6—C7—C8	−179.17 (10)	C17—C18—C19—C20	1.01 (18)
C3—C6—C7—C8	−0.26 (17)	C16—C15—C20—C19	0.46 (18)
C6—C7—C8—C1	1.31 (18)	C5—C15—C20—C19	176.09 (10)
C2—C1—C8—C7	−0.51 (17)	C18—C19—C20—C15	−1.44 (18)
C1i—C1—C8—C7	179.27 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···C18ii	0.977 (15)	2.722 (15)	3.5521 (16)	143.1 (12)
C7—H7···N2iii	0.979 (15)	2.593 (16)	3.3635 (15)	135.6 (11)
C10—H10···C3iv	0.974 (13)	2.935 (12)	3.2994 (15)	103.4 (8)
C10—H10···C6iv	0.974 (13)	2.974 (13)	3.1801 (15)	93.1 (8)
C11—H11···N1iv	0.963 (15)	2.893 (14)	3.3233 (14)	108.3 (10)
C12—H12···C18v	0.975 (15)	2.959 (15)	3.6146 (16)	125.6 (10)
C13—H13···C18v	0.999 (15)	2.978 (15)	3.6141 (16)	122.5 (10)
C16—H16···N2iv	0.978 (14)	2.815 (14)	3.7256 (14)	155.2 (11)
C17—H17···C1vi	0.969 (13)	2.993 (14)	3.7019 (16)	131.0 (9)
C17—H17···C8vi	0.969 (13)	2.860 (14)	3.6338 (15)	137.5 (9)
C18—H18···N1vii	0.975 (14)	2.808 (14)	3.6217 (14)	141.5 (10)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯C18i	0.977 (15)	2.722 (15)	3.5521 (16)	143.1 (12)
C7—H7⋯N2ii	0.979 (15)	2.593 (16)	3.3635 (15)	135.6 (11)
C10—H10⋯C3iii	0.974 (13)	2.935 (12)	3.2994 (15)	103.4 (8)
C10—H10⋯C6iii	0.974 (13)	2.974 (13)	3.1801 (15)	93.1 (8)
C11—H11⋯N1iii	0.963 (15)	2.893 (14)	3.3233 (14)	108.3 (10)
C12—H12⋯C18iv	0.975 (15)	2.959 (15)	3.6146 (16)	125.6 (10)
C13—H13⋯C18iv	0.999 (15)	2.978 (15)	3.6141 (16)	122.5 (10)
C16—H16⋯N2iii	0.978 (14)	2.815 (14)	3.7256 (14)	155.2 (11)
C17—H17⋯C1v	0.969 (13)	2.993 (14)	3.7019 (16)	131.0 (9)
C17—H17⋯C8v	0.969 (13)	2.860 (14)	3.6338 (15)	137.5 (9)
C18—H18⋯N1vi	0.975 (14)	2.808 (14)	3.6217 (14)	141.5 (10)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .