6-Chloro-2-phenyl-3-(2-phenyl-ethyn-yl)quinoxaline.

In the title compound, C(22)H(13)ClN(2), the quinoxaline ring system is close to planar [maximum deviation = 0.061 (2) Å]. The phenyl ring at the 2-position and the phenyl ring of the phenyl-ethynyl substituent make dihedral angles of 49.32 (7) and 11.99 (7) °, respectively, with the quinoxaline mean plane. The two phenyl rings are inclined to one another by 61.27 (9)°. In the crystal, mol-ecules are linked by C-H⋯π and π-π inter-actions [centroid-centroid distances = 3.6210 (12) and 3.8091 (12) Å].

Related literature

For the biological activity of quinoxaline derivatives, see: Rodrigo et al. (2002 ▶); Watkins et al. (2009 ▶); Sashidhara et al. (2009 ▶). For the crystal structures of quinoxaline derivatives, see: Hegedus et al. (2003 ▶); Naraso et al. (2006 ▶); Hassan et al. (2010 ▶); Ammermann et al. (2008 ▶); Daouda et al. (2011 ▶); Ramli et al. (2012 ▶).

Experimental

Crystal data

C22H13ClN2

M = 340.79

Triclinic,

a = 8.8652 (13) Å

b = 9.8591 (8) Å

c = 10.9740 (17) Å

α = 73.032 (15)°

β = 81.036 (17)°

γ = 64.374 (13)°

V = 826.68 (19) Å3

Z = 2

Mo Kα radiation

μ = 0.24 mm−1

T = 223 K

0.70 × 0.45 × 0.20 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.649, T max = 0.954

7504 measured reflections

3714 independent reflections

2855 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.128

S = 1.07

3714 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.37 e Å−3

Data collection: CrystalClear (Rigaku, 2002 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalStructure (Rigaku, 2002 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812020776/su2414sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020776/su2414Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812020776/su2414Isup3.cml

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

C22H13ClN2	Z = 2
Mr = 340.79	F(000) = 352
Triclinic, P1	Dx = 1.369 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71075 Å
a = 8.8652 (13) Å	Cell parameters from 3874 reflections
b = 9.8591 (8) Å	θ = 3.2–27.5°
c = 10.9740 (17) Å	µ = 0.24 mm−1
α = 73.032 (15)°	T = 223 K
β = 81.036 (17)°	Block, yellow
γ = 64.374 (13)°	0.70 × 0.45 × 0.20 mm
V = 826.68 (19) Å3

Rigaku Saturn diffractometer	3714 independent reflections
Radiation source: fine-focus sealed tube	2855 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 14.63 pixels mm-1	θmax = 27.5°, θmin = 3.2°
ω scans	h = −11→9
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −12→12
Tmin = 0.649, Tmax = 0.954	l = −14→10
7504 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0712P)2] where P = (Fo2 + 2Fc2)/3
3714 reflections	(Δ/σ)max < 0.001
227 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

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	−0.11370 (6)	0.42900 (6)	1.28280 (4)	0.05093 (18)
N1	0.47258 (16)	0.32096 (14)	0.93213 (12)	0.0299 (3)
N2	0.26481 (16)	0.16607 (15)	0.94729 (12)	0.0314 (3)
C1	0.05364 (19)	0.40009 (19)	1.17229 (15)	0.0344 (4)
C2	0.1450 (2)	0.49110 (19)	1.15630 (15)	0.0349 (4)
H2	0.1121	0.5680	1.2012	0.042*
C3	0.28190 (19)	0.46636 (18)	1.07482 (15)	0.0326 (4)
H3	0.3446	0.5255	1.0643	0.039*
C4	0.32946 (18)	0.35241 (17)	1.00641 (14)	0.0286 (3)
C5	0.22960 (19)	0.26891 (18)	1.01856 (14)	0.0298 (3)
C6	0.0918 (2)	0.29202 (19)	1.10582 (15)	0.0338 (4)
H6	0.0276	0.2339	1.1178	0.041*
C7	0.51048 (19)	0.21689 (17)	0.86690 (14)	0.0292 (3)
C8	0.40000 (18)	0.14242 (17)	0.87130 (14)	0.0288 (3)
C9	0.67530 (19)	0.17448 (17)	0.79653 (15)	0.0308 (3)
C10	0.8145 (2)	0.14816 (19)	0.85823 (17)	0.0379 (4)
H10	0.8026	0.1569	0.9426	0.045*
C11	0.9711 (2)	0.1090 (2)	0.79661 (19)	0.0456 (5)
H11	1.0649	0.0899	0.8396	0.055*
C12	0.9889 (2)	0.0981 (2)	0.6723 (2)	0.0485 (5)
H12	1.0947	0.0714	0.6305	0.058*
C13	0.8506 (2)	0.1266 (2)	0.60934 (18)	0.0459 (5)
H13	0.8628	0.1209	0.5241	0.055*
C14	0.6945 (2)	0.16343 (19)	0.67054 (16)	0.0366 (4)
H14	0.6016	0.1810	0.6274	0.044*
C15	0.43695 (19)	0.03324 (18)	0.79721 (15)	0.0322 (4)
C16	0.4708 (2)	−0.06017 (18)	0.73719 (15)	0.0339 (4)
C17	0.5261 (2)	−0.17824 (18)	0.66936 (15)	0.0324 (4)
C18	0.6633 (2)	−0.1962 (2)	0.58335 (16)	0.0397 (4)
H18	0.7119	−0.1241	0.5638	0.048*
C19	0.7275 (2)	−0.3183 (2)	0.52727 (17)	0.0434 (4)
H19	0.8201	−0.3299	0.4699	0.052*
C20	0.6561 (2)	−0.4245 (2)	0.55506 (17)	0.0420 (4)
H20	0.7017	−0.5093	0.5179	0.050*
C21	0.5186 (2)	−0.4060 (2)	0.63702 (17)	0.0399 (4)
H21	0.4698	−0.4777	0.6547	0.048*
C22	0.4516 (2)	−0.28344 (19)	0.69351 (16)	0.0364 (4)
H22	0.3562	−0.2705	0.7481	0.044*

	U11	U22	U33	U12	U13	U23
Cl1	0.0412 (3)	0.0698 (3)	0.0470 (3)	−0.0267 (2)	0.0169 (2)	−0.0255 (2)
N1	0.0286 (6)	0.0311 (7)	0.0339 (7)	−0.0147 (6)	0.0008 (6)	−0.0106 (6)
N2	0.0298 (7)	0.0338 (7)	0.0353 (7)	−0.0166 (6)	−0.0003 (6)	−0.0103 (6)
C1	0.0287 (8)	0.0418 (9)	0.0311 (8)	−0.0133 (7)	0.0021 (7)	−0.0102 (7)
C2	0.0334 (8)	0.0378 (9)	0.0358 (9)	−0.0136 (7)	0.0004 (7)	−0.0151 (7)
C3	0.0332 (8)	0.0334 (8)	0.0358 (8)	−0.0158 (7)	−0.0027 (7)	−0.0112 (7)
C4	0.0255 (7)	0.0310 (8)	0.0307 (8)	−0.0131 (7)	−0.0008 (6)	−0.0075 (7)
C5	0.0287 (8)	0.0306 (8)	0.0309 (8)	−0.0127 (7)	−0.0032 (6)	−0.0070 (7)
C6	0.0306 (8)	0.0387 (9)	0.0356 (8)	−0.0181 (7)	0.0014 (7)	−0.0092 (7)
C7	0.0277 (8)	0.0296 (8)	0.0308 (8)	−0.0129 (6)	−0.0011 (6)	−0.0062 (6)
C8	0.0272 (7)	0.0281 (8)	0.0325 (8)	−0.0115 (6)	−0.0018 (7)	−0.0089 (7)
C9	0.0287 (8)	0.0277 (8)	0.0386 (8)	−0.0145 (7)	0.0044 (7)	−0.0100 (7)
C10	0.0348 (9)	0.0410 (9)	0.0446 (9)	−0.0194 (8)	0.0025 (8)	−0.0164 (8)
C11	0.0289 (8)	0.0484 (11)	0.0660 (12)	−0.0191 (8)	0.0024 (9)	−0.0207 (9)
C12	0.0356 (9)	0.0501 (11)	0.0656 (12)	−0.0230 (9)	0.0192 (9)	−0.0254 (10)
C13	0.0480 (10)	0.0495 (11)	0.0443 (10)	−0.0244 (9)	0.0154 (9)	−0.0195 (9)
C14	0.0358 (9)	0.0390 (9)	0.0380 (9)	−0.0177 (8)	0.0043 (7)	−0.0130 (7)
C15	0.0297 (8)	0.0339 (8)	0.0372 (9)	−0.0161 (7)	−0.0002 (7)	−0.0105 (7)
C16	0.0333 (8)	0.0340 (9)	0.0372 (9)	−0.0165 (7)	−0.0018 (7)	−0.0082 (7)
C17	0.0331 (8)	0.0313 (8)	0.0343 (8)	−0.0132 (7)	−0.0034 (7)	−0.0096 (7)
C18	0.0445 (10)	0.0375 (9)	0.0411 (9)	−0.0212 (8)	0.0023 (8)	−0.0107 (8)
C19	0.0442 (10)	0.0480 (10)	0.0386 (9)	−0.0195 (9)	0.0078 (8)	−0.0157 (8)
C20	0.0511 (10)	0.0369 (9)	0.0404 (9)	−0.0144 (8)	−0.0025 (8)	−0.0182 (8)
C21	0.0454 (10)	0.0386 (9)	0.0447 (10)	−0.0219 (8)	−0.0052 (8)	−0.0140 (8)
C22	0.0357 (9)	0.0385 (9)	0.0406 (9)	−0.0177 (8)	−0.0005 (7)	−0.0143 (8)

Cl1—C1	1.7401 (16)	C11—C12	1.378 (3)
N1—C7	1.3168 (18)	C11—H11	0.9400
N1—C4	1.3621 (18)	C12—C13	1.383 (3)
N2—C8	1.3216 (19)	C12—H12	0.9400
N2—C5	1.3602 (19)	C13—C14	1.384 (2)
C1—C6	1.359 (2)	C13—H13	0.9400
C1—C2	1.408 (2)	C14—H14	0.9400
C2—C3	1.366 (2)	C15—C16	1.194 (2)
C2—H2	0.9400	C16—C17	1.431 (2)
C3—C4	1.410 (2)	C17—C18	1.398 (2)
C3—H3	0.9400	C17—C22	1.400 (2)
C4—C5	1.417 (2)	C18—C19	1.373 (2)
C5—C6	1.408 (2)	C18—H18	0.9400
C6—H6	0.9400	C19—C20	1.384 (2)
C7—C8	1.445 (2)	C19—H19	0.9400
C7—C9	1.488 (2)	C20—C21	1.375 (2)
C8—C15	1.432 (2)	C20—H20	0.9400
C9—C10	1.389 (2)	C21—C22	1.378 (2)
C9—C14	1.397 (2)	C21—H21	0.9400
C10—C11	1.389 (2)	C22—H22	0.9400
C10—H10	0.9400
C7—N1—C4	118.09 (11)	C12—C11—C10	119.90 (17)
C8—N2—C5	117.11 (12)	C12—C11—H11	120.1
C6—C1—C2	122.68 (14)	C10—C11—H11	120.1
C6—C1—Cl1	119.67 (12)	C11—C12—C13	119.87 (16)
C2—C1—Cl1	117.65 (12)	C11—C12—H12	120.1
C3—C2—C1	119.21 (14)	C13—C12—H12	120.1
C3—C2—H2	120.4	C12—C13—C14	120.66 (17)
C1—C2—H2	120.4	C12—C13—H13	119.7
C2—C3—C4	120.20 (13)	C14—C13—H13	119.7
C2—C3—H3	119.9	C13—C14—C9	119.90 (16)
C4—C3—H3	119.9	C13—C14—H14	120.0
N1—C4—C3	119.84 (12)	C9—C14—H14	120.0
N1—C4—C5	120.75 (13)	C16—C15—C8	178.49 (18)
C3—C4—C5	119.39 (13)	C15—C16—C17	174.90 (17)
N2—C5—C6	119.21 (12)	C18—C17—C22	118.90 (14)
N2—C5—C4	121.04 (13)	C18—C17—C16	120.00 (13)
C6—C5—C4	119.75 (13)	C22—C17—C16	120.97 (14)
C1—C6—C5	118.58 (13)	C19—C18—C17	120.41 (14)
C1—C6—H6	120.7	C19—C18—H18	119.8
C5—C6—H6	120.7	C17—C18—H18	119.8
N1—C7—C8	120.60 (12)	C18—C19—C20	120.15 (15)
N1—C7—C9	116.64 (12)	C18—C19—H19	119.9
C8—C7—C9	122.65 (12)	C20—C19—H19	119.9
N2—C8—C15	116.82 (12)	C21—C20—C19	119.98 (14)
N2—C8—C7	122.04 (12)	C21—C20—H20	120.0
C15—C8—C7	121.08 (13)	C19—C20—H20	120.0
C10—C9—C14	118.97 (14)	C20—C21—C22	120.73 (14)
C10—C9—C7	118.40 (14)	C20—C21—H21	119.6
C14—C9—C7	122.62 (15)	C22—C21—H21	119.6
C9—C10—C11	120.69 (16)	C21—C22—C17	119.76 (15)
C9—C10—H10	119.7	C21—C22—H22	120.1
C11—C10—H10	119.7	C17—C22—H22	120.1
C6—C1—C2—C3	−2.8 (3)	N1—C7—C9—C10	44.3 (2)
Cl1—C1—C2—C3	176.92 (13)	C8—C7—C9—C10	−132.03 (16)
C1—C2—C3—C4	0.9 (3)	N1—C7—C9—C14	−134.37 (16)
C7—N1—C4—C3	−178.15 (14)	C8—C7—C9—C14	49.3 (2)
C7—N1—C4—C5	3.5 (2)	C14—C9—C10—C11	−1.0 (2)
C2—C3—C4—N1	−175.48 (15)	C7—C9—C10—C11	−179.69 (14)
C2—C3—C4—C5	2.9 (2)	C9—C10—C11—C12	0.9 (3)
C8—N2—C5—C6	−176.75 (14)	C10—C11—C12—C13	0.1 (3)
C8—N2—C5—C4	3.1 (2)	C11—C12—C13—C14	−1.1 (3)
N1—C4—C5—N2	−6.4 (2)	C12—C13—C14—C9	1.0 (3)
C3—C4—C5—N2	175.30 (14)	C10—C9—C14—C13	0.0 (2)
N1—C4—C5—C6	173.49 (14)	C7—C9—C14—C13	178.65 (14)
C3—C4—C5—C6	−4.8 (2)	N2—C8—C15—C16	−108 (6)
C2—C1—C6—C5	0.8 (3)	C7—C8—C15—C16	70 (6)
Cl1—C1—C6—C5	−178.91 (12)	C8—C15—C16—C17	−23 (7)
N2—C5—C6—C1	−177.12 (15)	C15—C16—C17—C18	−56.4 (18)
C4—C5—C6—C1	3.0 (2)	C15—C16—C17—C22	119.5 (18)
C4—N1—C7—C8	2.0 (2)	C22—C17—C18—C19	−2.4 (3)
C4—N1—C7—C9	−174.41 (13)	C16—C17—C18—C19	173.60 (16)
C5—N2—C8—C15	179.58 (14)	C17—C18—C19—C20	0.3 (3)
C5—N2—C8—C7	2.5 (2)	C18—C19—C20—C21	1.3 (3)
N1—C7—C8—N2	−5.3 (2)	C19—C20—C21—C22	−0.8 (3)
C9—C7—C8—N2	170.89 (15)	C20—C21—C22—C17	−1.3 (3)
N1—C7—C8—C15	177.74 (14)	C18—C17—C22—C21	2.9 (3)
C9—C7—C8—C15	−6.1 (2)	C16—C17—C22—C21	−173.08 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···Cg2i	0.94	3.00	3.845 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C17–C22 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯Cg2i	0.94	3.00	3.845 (2)	151

Symmetry code: (i) .