2-(2-Chloro-phen-yl)-3-(3,4-dimeth-oxy-phen-yl)quinoxaline.

The title compound, C(22)H(17)ClN(2)O(2), was synthesized by the condensation reaction between 1,2-phenyl-enediamine and 2-chloro-3',4'-dimeth-oxy-benzil in boiling acetic acid. The chloro-phenyl and dimeth-oxy-phenyl rings make dihedral angles of 78.45 (5) and 35.60 (4)°, respectively, with the quinoxaline unit.

Related literature

N-heterocyclic aromatic compounds are of current inter­est as ligands in one- and two-dimensional coordination polymers with silver, see: Fitchett & Steel (2006 ▶). The quinoxaline moiety yields a wide variety of potential bidentate bridges in polymeric networks with silver, see: Patra et al. (2007 ▶). For the synthesis and characterization of quinoxalines, see: Crundwell & Stacy (2005 ▶), of benzo[g]quinoxalines, see: Cantalupo et al. (2006 ▶) and of pyrazino­[2,3-g]quinoxalines, see: Bellizzi et al. (2006 ▶).

Experimental

Crystal data

C22H17ClN2O2

M = 376.83

Monoclinic,

a = 14.6741 (13) Å

b = 7.9731 (7) Å

c = 21.6996 (17) Å

β = 132.560 (6)°

V = 1870.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 293 K

0.42 × 0.24 × 0.19 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.699, T max = 1.000

46880 measured reflections

7159 independent reflections

4223 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.202

S = 1.03

7159 reflections

246 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.37 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810024864/ds2038sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024864/ds2038Isup2.hkl

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

C22H17ClN2O2	F(000) = 784
Mr = 376.83	Dx = 1.338 Mg m−3
Monoclinic, P21/c	Melting point: 407.8 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.6741 (13) Å	Cell parameters from 11257 reflections
b = 7.9731 (7) Å	θ = 4.3–34.1°
c = 21.6996 (17) Å	µ = 0.22 mm−1
β = 132.560 (6)°	T = 293 K
V = 1870.0 (3) Å3	Block, yellow
Z = 4	0.42 × 0.24 × 0.19 mm

Oxford Diffraction Xcalibur Sapphire3 diffractometer	7159 independent reflections
Radiation source: Enhance (Mo) X-ray Source	4223 reflections with I > 2σ(I)
graphite	Rint = 0.051
Detector resolution: 16.1790 pixels mm-1	θmax = 33.9°, θmin = 4.4°
ω scans	h = −22→22
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −12→12
Tmin = 0.699, Tmax = 1.000	l = −33→33
46880 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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.202	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0955P)2 + 0.4554P] where P = (Fo2 + 2Fc2)/3
7159 reflections	(Δ/σ)max < 0.001
246 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

Experimental. Hydrogen atoms were included in calculated positions with a C—H distance of 0.95 Å and were included in the refinement in riding motion approximation with Uiso = 1.2Ueq of the carrier atom.CrysAlisPro (Oxford Diffraction Ltd., 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
C1	0.25132 (14)	0.6495 (2)	0.51893 (9)	0.0385 (3)
N1	0.34516 (13)	0.7171 (2)	0.59164 (8)	0.0450 (3)
C2	0.12494 (14)	0.6840 (2)	0.47750 (9)	0.0370 (3)
N2	0.09944 (13)	0.7886 (2)	0.51157 (8)	0.0442 (3)
C3	0.19586 (15)	0.8590 (2)	0.58719 (9)	0.0408 (3)
C4	0.17061 (19)	0.9715 (3)	0.62465 (12)	0.0566 (5)
H4	0.0893	0.9985	0.5973	0.068*
C5	0.2658 (2)	1.0397 (3)	0.70076 (12)	0.0597 (5)
H5	0.2490	1.1132	0.7253	0.072*
C6	0.3897 (2)	1.0000 (3)	0.74291 (12)	0.0583 (5)
H6	0.4537	1.0465	0.7952	0.070*
C7	0.41593 (18)	0.8936 (3)	0.70727 (11)	0.0537 (5)
H7	0.4978	0.8684	0.7352	0.064*
C8	0.31893 (15)	0.8217 (2)	0.62808 (9)	0.0410 (3)
C9	0.28488 (14)	0.5376 (2)	0.48137 (9)	0.0413 (4)
C10	0.27772 (17)	0.3643 (3)	0.48187 (11)	0.0501 (4)
C11	0.30563 (18)	0.2628 (3)	0.44390 (13)	0.0590 (5)
H11	0.3005	0.1466	0.4446	0.071*
C12	0.34054 (19)	0.3366 (3)	0.40569 (13)	0.0647 (6)
H12	0.3583	0.2700	0.3798	0.078*
C13	0.3498 (2)	0.5088 (3)	0.40510 (14)	0.0652 (6)
H13	0.3744	0.5565	0.3792	0.078*
C14	0.32275 (16)	0.6126 (3)	0.44284 (12)	0.0524 (4)
H14	0.3295	0.7285	0.4426	0.063*
Cl1	0.23549 (8)	0.27027 (8)	0.53138 (5)	0.0854 (2)
C15	0.01547 (14)	0.6069 (2)	0.39677 (9)	0.0379 (3)
C16	0.00943 (14)	0.5764 (2)	0.33031 (10)	0.0396 (3)
H16	0.0777	0.6000	0.3370	0.047*
C17	−0.09655 (14)	0.5118 (2)	0.25514 (10)	0.0397 (3)
C18	−0.20106 (15)	0.4789 (2)	0.24403 (10)	0.0422 (4)
C19	−0.19425 (16)	0.5068 (2)	0.30999 (11)	0.0474 (4)
H19	−0.2622	0.4826	0.3036	0.057*
C20	−0.08736 (16)	0.5706 (2)	0.38564 (11)	0.0457 (4)
H20	−0.0847	0.5891	0.4291	0.055*
O1	−0.10954 (11)	0.47659 (19)	0.18770 (8)	0.0534 (3)
C21	−0.0123 (2)	0.5263 (3)	0.19222 (14)	0.0655 (6)
H21A	0.0016	0.6447	0.2027	0.098*
H21B	−0.0346	0.5012	0.1402	0.098*
H21C	0.0618	0.4667	0.2368	0.098*
O2	−0.30319 (12)	0.42185 (19)	0.16651 (8)	0.0567 (4)
C22	−0.4155 (2)	0.4121 (4)	0.14824 (15)	0.0743 (7)
H22A	−0.4075	0.3313	0.1845	0.111*
H22B	−0.4808	0.3785	0.0910	0.111*
H22C	−0.4345	0.5199	0.1568	0.111*

	U11	U22	U33	U12	U13	U23
C1	0.0357 (7)	0.0417 (8)	0.0320 (7)	0.0051 (6)	0.0204 (6)	0.0026 (6)
N1	0.0359 (6)	0.0552 (9)	0.0349 (6)	0.0019 (6)	0.0203 (6)	−0.0007 (6)
C2	0.0338 (7)	0.0411 (8)	0.0293 (6)	0.0050 (6)	0.0186 (6)	0.0025 (6)
N2	0.0368 (6)	0.0536 (8)	0.0321 (6)	0.0080 (6)	0.0193 (5)	−0.0007 (6)
C3	0.0417 (8)	0.0429 (8)	0.0317 (7)	0.0051 (6)	0.0223 (6)	0.0019 (6)
C4	0.0561 (11)	0.0628 (12)	0.0428 (9)	0.0140 (9)	0.0302 (9)	−0.0030 (8)
C5	0.0749 (13)	0.0549 (11)	0.0437 (9)	0.0048 (10)	0.0378 (10)	−0.0061 (8)
C6	0.0662 (12)	0.0590 (12)	0.0391 (8)	−0.0155 (10)	0.0315 (9)	−0.0108 (8)
C7	0.0441 (9)	0.0661 (12)	0.0392 (8)	−0.0103 (8)	0.0235 (7)	−0.0077 (8)
C8	0.0394 (8)	0.0446 (8)	0.0327 (7)	−0.0015 (6)	0.0218 (6)	0.0007 (6)
C9	0.0316 (7)	0.0486 (9)	0.0331 (7)	0.0069 (6)	0.0176 (6)	0.0021 (6)
C10	0.0454 (9)	0.0512 (10)	0.0430 (8)	0.0113 (8)	0.0256 (7)	0.0072 (7)
C11	0.0497 (10)	0.0554 (11)	0.0498 (10)	0.0138 (8)	0.0248 (9)	−0.0027 (8)
C12	0.0530 (11)	0.0824 (16)	0.0535 (11)	0.0104 (10)	0.0339 (10)	−0.0119 (10)
C13	0.0634 (12)	0.0839 (16)	0.0655 (13)	−0.0011 (11)	0.0504 (11)	−0.0087 (11)
C14	0.0441 (9)	0.0675 (12)	0.0512 (10)	0.0010 (8)	0.0345 (8)	−0.0038 (9)
Cl1	0.1261 (6)	0.0590 (4)	0.1054 (5)	0.0107 (3)	0.0921 (5)	0.0207 (3)
C15	0.0331 (7)	0.0407 (8)	0.0318 (7)	0.0055 (6)	0.0187 (6)	0.0020 (6)
C16	0.0323 (7)	0.0445 (8)	0.0358 (7)	0.0019 (6)	0.0206 (6)	−0.0008 (6)
C17	0.0379 (7)	0.0402 (8)	0.0350 (7)	0.0024 (6)	0.0222 (6)	−0.0015 (6)
C18	0.0361 (7)	0.0378 (8)	0.0403 (8)	−0.0029 (6)	0.0208 (6)	−0.0038 (6)
C19	0.0407 (8)	0.0528 (10)	0.0490 (9)	−0.0066 (7)	0.0305 (8)	−0.0023 (8)
C20	0.0433 (8)	0.0528 (10)	0.0413 (8)	0.0004 (7)	0.0287 (7)	0.0002 (7)
O1	0.0455 (7)	0.0715 (9)	0.0404 (6)	−0.0064 (6)	0.0279 (6)	−0.0139 (6)
C21	0.0643 (12)	0.0865 (16)	0.0571 (11)	−0.0110 (11)	0.0456 (11)	−0.0154 (11)
O2	0.0420 (6)	0.0675 (9)	0.0488 (7)	−0.0163 (6)	0.0259 (6)	−0.0196 (6)
C22	0.0475 (11)	0.0965 (19)	0.0659 (13)	−0.0286 (11)	0.0332 (10)	−0.0219 (13)

C1—N1	1.318 (2)	C12—H12	0.9300
C1—C2	1.438 (2)	C13—C14	1.397 (3)
C1—C9	1.499 (2)	C13—H13	0.9300
N1—C8	1.371 (2)	C14—H14	0.9300
C2—N2	1.325 (2)	C15—C20	1.388 (2)
C2—C15	1.490 (2)	C15—C16	1.405 (2)
N2—C3	1.367 (2)	C16—C17	1.383 (2)
C3—C8	1.403 (2)	C16—H16	0.9300
C3—C4	1.418 (2)	C17—O1	1.371 (2)
C4—C5	1.362 (3)	C17—C18	1.407 (2)
C4—H4	0.9300	C18—O2	1.368 (2)
C5—C6	1.411 (3)	C18—C19	1.384 (3)
C5—H5	0.9300	C19—C20	1.389 (2)
C6—C7	1.367 (3)	C19—H19	0.9300
C6—H6	0.9300	C20—H20	0.9300
C7—C8	1.414 (2)	O1—C21	1.419 (3)
C7—H7	0.9300	C21—H21A	0.9600
C9—C10	1.386 (3)	C21—H21B	0.9600
C9—C14	1.412 (3)	C21—H21C	0.9600
C10—C11	1.400 (3)	O2—C22	1.412 (3)
C10—Cl1	1.732 (2)	C22—H22A	0.9600
C11—C12	1.368 (3)	C22—H22B	0.9600
C11—H11	0.9300	C22—H22C	0.9600
C12—C13	1.381 (4)
N1—C1—C2	122.11 (15)	C12—C13—C14	121.0 (2)
N1—C1—C9	115.67 (14)	C12—C13—H13	119.5
C2—C1—C9	122.21 (13)	C14—C13—H13	119.5
C1—N1—C8	117.75 (14)	C13—C14—C9	118.5 (2)
N2—C2—C1	120.19 (14)	C13—C14—H14	120.7
N2—C2—C15	115.39 (13)	C9—C14—H14	120.7
C1—C2—C15	124.41 (14)	C20—C15—C16	118.62 (14)
C2—N2—C3	118.32 (14)	C20—C15—C2	118.11 (14)
N2—C3—C8	121.09 (15)	C16—C15—C2	123.21 (14)
N2—C3—C4	119.23 (16)	C17—C16—C15	121.01 (15)
C8—C3—C4	119.69 (16)	C17—C16—H16	119.5
C5—C4—C3	119.79 (19)	C15—C16—H16	119.5
C5—C4—H4	120.1	O1—C17—C16	124.67 (15)
C3—C4—H4	120.1	O1—C17—C18	115.51 (14)
C4—C5—C6	120.75 (19)	C16—C17—C18	119.82 (15)
C4—C5—H5	119.6	O2—C18—C19	125.31 (16)
C6—C5—H5	119.6	O2—C18—C17	115.67 (16)
C7—C6—C5	120.32 (17)	C19—C18—C17	119.02 (15)
C7—C6—H6	119.8	C18—C19—C20	121.00 (16)
C5—C6—H6	119.8	C18—C19—H19	119.5
C6—C7—C8	120.12 (18)	C20—C19—H19	119.5
C6—C7—H7	119.9	C15—C20—C19	120.50 (16)
C8—C7—H7	119.9	C15—C20—H20	119.7
N1—C8—C3	120.49 (14)	C19—C20—H20	119.7
N1—C8—C7	120.19 (16)	C17—O1—C21	117.50 (14)
C3—C8—C7	119.31 (17)	O1—C21—H21A	109.5
C10—C9—C14	119.28 (17)	O1—C21—H21B	109.5
C10—C9—C1	122.33 (16)	H21A—C21—H21B	109.5
C14—C9—C1	118.37 (16)	O1—C21—H21C	109.5
C9—C10—C11	121.20 (19)	H21A—C21—H21C	109.5
C9—C10—Cl1	119.82 (15)	H21B—C21—H21C	109.5
C11—C10—Cl1	118.97 (17)	C18—O2—C22	117.59 (16)
C12—C11—C10	119.1 (2)	O2—C22—H22A	109.5
C12—C11—H11	120.4	O2—C22—H22B	109.5
C10—C11—H11	120.4	H22A—C22—H22B	109.5
C11—C12—C13	120.9 (2)	O2—C22—H22C	109.5
C11—C12—H12	119.6	H22A—C22—H22C	109.5
C13—C12—H12	119.6	H22B—C22—H22C	109.5