2,3-Diphenyl-quinoxalin-1-ium chloride.

The title compound, C(20)H(15)N(2) (+)·Cl(-), was prepared by the reaction of benzil with o-phenyl-enediamine in refluxing ethanol and then crystallized in 5% hydro-chloric acid. The two phenyl rings are oriented at dihedral angles of 50.93 (8) and 50.28 (8)° with respect to the quinoxalin-1-ium ring system. The dihedral angle between the two phenyl rings is 56.71 (10)°. In the crystal, the cations and anions are linked by N-H⋯Cl and C-H⋯Cl inter-actions, forming chains along the b axis.

Related literature

For general background to quinoxaline derivatives, see: Brock et al. (1999 ▶); Dailey et al. (2001 ▶); Page et al. (1998 ▶); Pascal et al. (1993 ▶). For a related structure, see: Wu et al. (2002 ▶).

Experimental

Crystal data

C20H15N2 +·Cl−

M = 318.79

Monoclinic,

a = 10.498 (3) Å

b = 14.773 (5) Å

c = 11.359 (4) Å

β = 112.692 (3)°

V = 1625.3 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 293 K

0.25 × 0.22 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.943, T max = 0.954

9558 measured reflections

2893 independent reflections

2257 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.109

S = 1.06

2893 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAIn class="Chemical">NT; 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: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810023883/ci5102sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023883/ci5102Isup2.hkl

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

C20H15N2+·Cl−	F(000) = 664
Mr = 318.79	Dx = 1.303 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2838 reflections
a = 10.498 (3) Å	θ = 2.1–25.1°
b = 14.773 (5) Å	µ = 0.24 mm−1
c = 11.359 (4) Å	T = 293 K
β = 112.692 (3)°	Block, yellow
V = 1625.3 (9) Å3	0.25 × 0.22 × 0.20 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2893 independent reflections
Radiation source: fine-focus sealed tube	2257 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 25.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −12→12
Tmin = 0.943, Tmax = 0.954	k = −17→17
9558 measured reflections	l = −13→10

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) = 0.109	w = 1/[σ2(Fo2) + (0.0549P)2 + 0.2666P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
2893 reflections	Δρmax = 0.18 e Å−3
209 parameters	Δρmin = −0.24 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.068 (4)

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
Cl1	−0.00715 (5)	0.21487 (3)	0.19706 (5)	0.0593 (2)
C13	0.25287 (17)	0.73467 (11)	0.12361 (16)	0.0396 (4)
C6	0.23732 (18)	0.83023 (11)	0.15477 (17)	0.0410 (4)
C14	0.35118 (18)	0.70084 (11)	0.07464 (17)	0.0420 (4)
C1	0.35195 (19)	0.88047 (12)	0.22987 (19)	0.0497 (5)
H1	0.4398	0.8553	0.2571	0.060*
C12	0.44507 (19)	0.76230 (12)	0.04193 (17)	0.0442 (4)
C20	0.18022 (19)	0.58334 (11)	0.13075 (17)	0.0456 (4)
C8	0.6742 (2)	0.79882 (16)	0.0578 (2)	0.0698 (6)
H8	0.7683	0.7863	0.0901	0.084*
C5	0.10701 (19)	0.86889 (12)	0.11425 (18)	0.0483 (5)
H5	0.0297	0.8355	0.0649	0.058*
C2	0.3345 (2)	0.96830 (13)	0.2638 (2)	0.0593 (5)
H2	0.4108	1.0016	0.3154	0.071*
C15	0.2795 (2)	0.55363 (12)	0.08495 (17)	0.0483 (5)
C4	0.0922 (2)	0.95729 (13)	0.14748 (19)	0.0544 (5)
H4	0.0048	0.9834	0.1190	0.065*
C3	0.2050 (2)	1.00672 (13)	0.2220 (2)	0.0586 (6)
H3	0.1941	1.0660	0.2442	0.070*
C18	0.1142 (2)	0.43199 (14)	0.1498 (2)	0.0664 (6)
H18	0.0618	0.3905	0.1734	0.080*
C7	0.5854 (2)	0.74393 (14)	0.0890 (2)	0.0578 (5)
H7	0.6200	0.6942	0.1421	0.069*
C17	0.2095 (3)	0.40062 (13)	0.1005 (2)	0.0677 (6)
H17	0.2171	0.3388	0.0895	0.081*
C11	0.3943 (2)	0.83694 (13)	−0.03710 (18)	0.0508 (5)
H11	0.3006	0.8505	−0.0680	0.061*
C19	0.0969 (2)	0.52241 (13)	0.16366 (19)	0.0564 (5)
H19	0.0317	0.5430	0.1941	0.068*
C16	0.2915 (2)	0.45917 (13)	0.0684 (2)	0.0604 (6)
H16	0.3545	0.4374	0.0360	0.072*
C10	0.4835 (2)	0.89082 (15)	−0.0695 (2)	0.0642 (6)
H10	0.4493	0.9398	−0.1240	0.077*
C9	0.6229 (2)	0.87214 (17)	−0.0213 (2)	0.0733 (7)
H9	0.6827	0.9092	−0.0422	0.088*
N1	0.17297 (15)	0.67478 (9)	0.14856 (14)	0.0431 (4)
H1A	0.1134	0.6942	0.1774	0.052*
N2	0.36430 (16)	0.61318 (10)	0.05822 (15)	0.0489 (4)

	U11	U22	U33	U12	U13	U23
Cl1	0.0709 (4)	0.0488 (3)	0.0721 (4)	−0.0091 (2)	0.0429 (3)	−0.0097 (2)
C13	0.0447 (9)	0.0376 (9)	0.0363 (10)	0.0010 (7)	0.0152 (8)	0.0010 (7)
C6	0.0522 (10)	0.0352 (9)	0.0420 (10)	0.0013 (8)	0.0251 (8)	0.0027 (8)
C14	0.0503 (10)	0.0391 (9)	0.0378 (10)	0.0026 (8)	0.0183 (8)	−0.0010 (7)
C1	0.0525 (11)	0.0440 (10)	0.0567 (12)	0.0004 (8)	0.0256 (9)	−0.0038 (9)
C12	0.0537 (11)	0.0414 (9)	0.0436 (11)	0.0014 (8)	0.0257 (9)	−0.0053 (8)
C20	0.0562 (11)	0.0367 (9)	0.0413 (10)	−0.0013 (8)	0.0162 (9)	−0.0007 (8)
C8	0.0539 (12)	0.0829 (16)	0.0802 (16)	0.0013 (11)	0.0342 (12)	0.0017 (13)
C5	0.0530 (11)	0.0476 (10)	0.0475 (11)	0.0025 (8)	0.0230 (9)	0.0024 (8)
C2	0.0686 (13)	0.0436 (10)	0.0722 (15)	−0.0085 (10)	0.0343 (12)	−0.0121 (10)
C15	0.0598 (11)	0.0384 (9)	0.0449 (11)	0.0005 (8)	0.0183 (9)	−0.0008 (8)
C4	0.0653 (13)	0.0503 (11)	0.0570 (12)	0.0179 (10)	0.0339 (11)	0.0089 (10)
C3	0.0823 (15)	0.0378 (10)	0.0691 (14)	0.0048 (10)	0.0441 (12)	−0.0011 (9)
C18	0.0847 (16)	0.0457 (11)	0.0668 (14)	−0.0142 (11)	0.0272 (12)	0.0036 (10)
C7	0.0577 (12)	0.0540 (11)	0.0684 (14)	0.0113 (10)	0.0317 (11)	0.0039 (10)
C17	0.0913 (16)	0.0349 (10)	0.0705 (15)	−0.0045 (11)	0.0242 (13)	−0.0022 (10)
C11	0.0544 (11)	0.0532 (11)	0.0456 (11)	−0.0004 (9)	0.0201 (9)	0.0025 (9)
C19	0.0684 (13)	0.0457 (11)	0.0567 (13)	−0.0071 (9)	0.0261 (10)	0.0020 (9)
C16	0.0754 (14)	0.0397 (10)	0.0624 (13)	0.0030 (10)	0.0225 (11)	−0.0066 (9)
C10	0.0742 (15)	0.0642 (13)	0.0553 (13)	−0.0057 (11)	0.0264 (11)	0.0136 (11)
C9	0.0718 (15)	0.0853 (16)	0.0735 (16)	−0.0172 (13)	0.0398 (13)	0.0062 (13)
N1	0.0508 (9)	0.0383 (8)	0.0444 (9)	0.0024 (7)	0.0230 (7)	0.0014 (7)
N2	0.0590 (9)	0.0388 (8)	0.0508 (10)	0.0033 (7)	0.0234 (8)	−0.0024 (7)

C13—N1	1.323 (2)	C2—H2	0.93
C13—C14	1.438 (2)	C15—N2	1.367 (2)
C13—C6	1.480 (2)	C15—C16	1.420 (3)
C6—C5	1.387 (2)	C4—C3	1.371 (3)
C6—C1	1.391 (3)	C4—H4	0.93
C14—N2	1.323 (2)	C3—H3	0.93
C14—C12	1.489 (2)	C18—C19	1.365 (3)
C1—C2	1.386 (3)	C18—C17	1.400 (3)
C1—H1	0.93	C18—H18	0.93
C12—C7	1.387 (3)	C7—H7	0.93
C12—C11	1.392 (3)	C17—C16	1.366 (3)
C20—N1	1.372 (2)	C17—H17	0.93
C20—C19	1.402 (3)	C11—C10	1.383 (3)
C20—C15	1.403 (2)	C11—H11	0.93
C8—C9	1.377 (3)	C19—H19	0.93
C8—C7	1.381 (3)	C16—H16	0.93
C8—H8	0.93	C10—C9	1.379 (3)
C5—C4	1.385 (3)	C10—H10	0.93
C5—H5	0.93	C9—H9	0.93
C2—C3	1.378 (3)	N1—H1A	0.86
N1—C13—C14	117.35 (15)	C5—C4—H4	119.7
N1—C13—C6	116.70 (15)	C4—C3—C2	119.74 (18)
C14—C13—C6	125.88 (15)	C4—C3—H3	120.1
C5—C6—C1	119.53 (16)	C2—C3—H3	120.1
C5—C6—C13	119.95 (16)	C19—C18—C17	121.2 (2)
C1—C6—C13	120.44 (16)	C19—C18—H18	119.4
N2—C14—C13	121.60 (16)	C17—C18—H18	119.4
N2—C14—C12	116.54 (15)	C8—C7—C12	120.5 (2)
C13—C14—C12	121.85 (14)	C8—C7—H7	119.7
C2—C1—C6	119.62 (18)	C12—C7—H7	119.7
C2—C1—H1	120.2	C16—C17—C18	121.22 (19)
C6—C1—H1	120.2	C16—C17—H17	119.4
C7—C12—C11	119.33 (18)	C18—C17—H17	119.4
C7—C12—C14	119.44 (17)	C10—C11—C12	119.84 (18)
C11—C12—C14	121.22 (16)	C10—C11—H11	120.1
N1—C20—C19	121.12 (17)	C12—C11—H11	120.1
N1—C20—C15	117.01 (15)	C18—C19—C20	118.2 (2)
C19—C20—C15	121.79 (16)	C18—C19—H19	120.9
C9—C8—C7	119.8 (2)	C20—C19—H19	120.9
C9—C8—H8	120.1	C17—C16—C15	119.3 (2)
C7—C8—H8	120.1	C17—C16—H16	120.3
C4—C5—C6	119.88 (18)	C15—C16—H16	120.3
C4—C5—H5	120.1	C9—C10—C11	120.2 (2)
C6—C5—H5	120.1	C9—C10—H10	119.9
C3—C2—C1	120.58 (19)	C11—C10—H10	119.9
C3—C2—H2	119.7	C8—C9—C10	120.3 (2)
C1—C2—H2	119.7	C8—C9—H9	119.9
N2—C15—C20	121.46 (16)	C10—C9—H9	119.9
N2—C15—C16	120.29 (18)	C13—N1—C20	123.43 (15)
C20—C15—C16	118.24 (17)	C13—N1—H1A	118.3
C3—C4—C5	120.63 (18)	C20—N1—H1A	118.3
C3—C4—H4	119.7	C14—N2—C15	119.11 (16)
N1—C13—C6—C5	−49.4 (2)	C9—C8—C7—C12	−0.4 (3)
C14—C13—C6—C5	133.74 (19)	C11—C12—C7—C8	−0.2 (3)
N1—C13—C6—C1	127.41 (18)	C14—C12—C7—C8	178.61 (19)
C14—C13—C6—C1	−49.4 (3)	C19—C18—C17—C16	2.1 (3)
N1—C13—C14—N2	−1.8 (3)	C7—C12—C11—C10	1.1 (3)
C6—C13—C14—N2	175.02 (17)	C14—C12—C11—C10	−177.61 (18)
N1—C13—C14—C12	179.30 (16)	C17—C18—C19—C20	−1.9 (3)
C6—C13—C14—C12	−3.9 (3)	N1—C20—C19—C18	−176.65 (19)
C5—C6—C1—C2	0.4 (3)	C15—C20—C19—C18	−0.2 (3)
C13—C6—C1—C2	−176.49 (17)	C18—C17—C16—C15	−0.2 (3)
N2—C14—C12—C7	−49.1 (2)	N2—C15—C16—C17	177.39 (19)
C13—C14—C12—C7	129.83 (19)	C20—C15—C16—C17	−1.8 (3)
N2—C14—C12—C11	129.61 (18)	C12—C11—C10—C9	−1.6 (3)
C13—C14—C12—C11	−51.4 (2)	C7—C8—C9—C10	−0.1 (4)
C1—C6—C5—C4	0.8 (3)	C11—C10—C9—C8	1.1 (4)
C13—C6—C5—C4	177.62 (16)	C14—C13—N1—C20	0.4 (2)
C6—C1—C2—C3	−1.2 (3)	C6—C13—N1—C20	−176.73 (16)
N1—C20—C15—N2	−0.6 (3)	C19—C20—N1—C13	177.36 (17)
C19—C20—C15—N2	−177.17 (17)	C15—C20—N1—C13	0.7 (3)
N1—C20—C15—C16	178.58 (17)	C13—C14—N2—C15	2.0 (3)
C19—C20—C15—C16	2.0 (3)	C12—C14—N2—C15	−179.07 (15)
C6—C5—C4—C3	−1.1 (3)	C20—C15—N2—C14	−0.8 (3)
C5—C4—C3—C2	0.3 (3)	C16—C15—N2—C14	−179.90 (18)
C1—C2—C3—C4	0.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1i	0.86	2.14	2.9684 (16)	160
C18—H18···Cl1	0.93	2.73	3.568 (2)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl1i	0.86	2.14	2.9684 (16)	160
C18—H18⋯Cl1	0.93	2.73	3.568 (2)	150

Symmetry code: (i) .