Crystal structure of 1,3-bis­(2,3-di­methyl­quinoxalin-6-yl)benzene

The mol­ecular structure of the title complex is composed of a central benzene ring with 3-di­methyl­quinoxalin-6-yl groups at the 1 and 3 positions. There are inter­molecular π–π inter­actions which result in a two-dimensional extended structure. The layers extend parallel to the ab plane and stack along the c axis.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.047
• wR factor = 0.138
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.005 Check

Alert level G
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ...          1 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         27 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

   0 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
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014), XPREP (Bruker, 2014) and SADABS (Bruker, 2014); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and CrystalMaker (CrystalMaker, 1994); software used to prepare material for publication: XCIF (Bruker, 2014) and publCIF (Westrip, 2010).

1,3-Bis(2,3-dimethylquinoxalin-6-yl)benzene

Crystal data

C26H22N4	F(000) = 824
Mr = 390.47	Dx = 1.333 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1141 reflections
a = 6.828 (3) Å	θ = 3.4–26.1°
b = 11.837 (5) Å	µ = 0.08 mm^−1
c = 24.079 (11) Å	T = 173 K
β = 91.902 (5)°	Prism, orange
V = 1945.0 (15) Å^3	0.30 × 0.17 × 0.17 mm
Z = 4

Data collection

Siemens Platform/APEXII CCD diffractometer	1955 independent reflections
Radiation source: normal-focus sealed tube	1356 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.066
profile data from φ and ω scans	θmax = 26.3°, θmin = 3.4°
Absorption correction: integration (SADABS; Bruker, 2014)	h = −8→8
Tmin = 0.645, Tmax = 1.000	k = −14→14
7176 measured reflections	l = −29→29

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters not refined
R[F^2 > 2σ(F^2)] = 0.047	w = 1/[σ^2(Fo^2) + (0.060P)^2 + 0.4908P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.138	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.23 e Å^−3
1955 reflections	Δρmin = −0.22 e Å^−3
140 parameters	Extinction correction: SHELXTL (Bruker, 2014), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0082 (13)

Special details

Experimental. One distinct cell was identified using APEX2 (Bruker, 2014). Six frame series were integrated and filtered for statistical outliers using SAINT (Bruker, 2014) and then the combined data was corrected for absorption by integration, sorted, merged and scaled using SADABS (Bruker, 2014). No decay correction was applied.

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. Structure was phased by direct methods. Systematic conditions suggested the ambiguous space group. The space group choice was confirmed by successful convergence of the full-matrix least-squares refinement on F². The final difference Fourier map had no significant features. A final analysis of variance between observed and calculated structure factors showed little dependence on amplitude or resolution.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.8418 (2)	0.49563 (11)	0.40609 (6)	0.0291 (4)
N2	1.2363 (2)	0.57112 (12)	0.40420 (6)	0.0287 (4)
C1	0.5000	0.75167 (19)	0.2500	0.0262 (6)
H1A	0.5000	0.6714	0.2500	0.031*
C2	0.6402 (2)	0.80925 (14)	0.28278 (7)	0.0265 (4)
C3	0.6397 (3)	0.92738 (14)	0.28160 (7)	0.0294 (4)
H3A	0.7363	0.9680	0.3027	0.035*
C4	0.5000	0.9858 (2)	0.2500	0.0297 (6)
H4A	0.5000	1.0661	0.2500	0.036*
C5	0.7892 (2)	0.74799 (14)	0.31783 (7)	0.0273 (4)
C6	0.7440 (3)	0.65150 (13)	0.34720 (7)	0.0278 (4)
H6A	0.6127	0.6250	0.3469	0.033*
C7	0.8910 (3)	0.59216 (13)	0.37760 (7)	0.0266 (4)
C8	0.9866 (3)	0.43970 (14)	0.43105 (7)	0.0285 (4)
C9	1.1886 (3)	0.47661 (14)	0.42908 (7)	0.0286 (4)
C10	1.0870 (2)	0.63148 (14)	0.37843 (7)	0.0272 (4)
C11	1.1300 (3)	0.73199 (14)	0.35013 (7)	0.0290 (4)
H11A	1.2601	0.7605	0.3511	0.035*
C12	0.9854 (3)	0.78862 (14)	0.32128 (7)	0.0289 (4)
H12A	1.0165	0.8571	0.3030	0.035*
C13	0.9366 (3)	0.33468 (15)	0.46213 (8)	0.0343 (5)
H13A	0.7939	0.3282	0.4641	0.051*
H13B	0.9950	0.3384	0.4998	0.051*
H13C	0.9881	0.2687	0.4428	0.051*
C14	1.3495 (3)	0.40683 (15)	0.45522 (8)	0.0355 (5)
H14A	1.4766	0.4374	0.4449	0.053*
H14B	1.3373	0.3286	0.4422	0.053*
H14C	1.3399	0.4088	0.4957	0.053*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0268 (8)	0.0301 (8)	0.0305 (8)	−0.0014 (6)	0.0008 (7)	0.0005 (6)
N2	0.0240 (8)	0.0340 (8)	0.0280 (8)	0.0010 (6)	0.0013 (7)	−0.0021 (6)
C1	0.0236 (13)	0.0262 (12)	0.0290 (13)	0.000	0.0039 (11)	0.000
C2	0.0260 (10)	0.0298 (9)	0.0239 (9)	−0.0005 (7)	0.0050 (8)	0.0003 (7)
C3	0.0315 (11)	0.0305 (9)	0.0262 (9)	−0.0027 (7)	0.0015 (8)	−0.0030 (7)
C4	0.0360 (15)	0.0255 (12)	0.0278 (13)	0.000	0.0034 (12)	0.000
C5	0.0278 (10)	0.0297 (9)	0.0243 (9)	0.0006 (7)	−0.0004 (8)	−0.0031 (7)
C6	0.0219 (9)	0.0319 (9)	0.0295 (10)	−0.0019 (7)	0.0001 (8)	−0.0010 (7)
C7	0.0269 (10)	0.0292 (9)	0.0238 (9)	0.0000 (7)	0.0034 (8)	−0.0007 (7)
C8	0.0299 (10)	0.0289 (9)	0.0263 (9)	0.0012 (8)	−0.0016 (8)	−0.0017 (7)
C9	0.0304 (10)	0.0321 (9)	0.0233 (9)	0.0029 (7)	0.0001 (8)	−0.0047 (7)
C10	0.0241 (10)	0.0316 (9)	0.0257 (9)	0.0000 (7)	−0.0003 (8)	−0.0037 (7)
C11	0.0243 (10)	0.0339 (10)	0.0289 (10)	−0.0050 (7)	0.0024 (8)	−0.0037 (7)
C12	0.0291 (10)	0.0317 (9)	0.0258 (9)	−0.0032 (7)	0.0022 (8)	−0.0001 (7)
C13	0.0338 (11)	0.0333 (10)	0.0355 (11)	0.0010 (8)	−0.0029 (9)	0.0049 (8)
C14	0.0299 (11)	0.0392 (10)	0.0371 (11)	0.0045 (8)	−0.0015 (9)	0.0015 (8)

Geometric parameters (Å, º)

N1—C8	1.318 (2)	C6—H6A	0.9500
N1—C7	1.380 (2)	C7—C10	1.416 (2)
N2—C9	1.315 (2)	C8—C9	1.449 (3)
N2—C10	1.376 (2)	C8—C13	1.496 (2)
C1—C2	1.3980 (19)	C9—C14	1.496 (2)
C1—C2^i	1.3980 (19)	C10—C11	1.407 (2)
C1—H1A	0.9500	C11—C12	1.364 (2)
C2—C3	1.399 (2)	C11—H11A	0.9500
C2—C5	1.488 (2)	C12—H12A	0.9500
C3—C4	1.385 (2)	C13—H13A	0.9800
C3—H3A	0.9500	C13—H13B	0.9800
C4—C3^i	1.385 (2)	C13—H13C	0.9800
C4—H4A	0.9500	C14—H14A	0.9800
C5—C6	1.384 (2)	C14—H14B	0.9800
C5—C12	1.423 (2)	C14—H14C	0.9800
C6—C7	1.410 (2)
C8—N1—C7	116.81 (15)	C9—C8—C13	120.00 (15)
C9—N2—C10	117.13 (15)	N2—C9—C8	121.45 (15)
C2—C1—C2^i	121.6 (2)	N2—C9—C14	118.15 (16)
C2—C1—H1A	119.2	C8—C9—C14	120.40 (16)
C2^i—C1—H1A	119.2	N2—C10—C11	119.60 (16)
C1—C2—C3	118.34 (16)	N2—C10—C7	121.43 (16)
C1—C2—C5	121.66 (16)	C11—C10—C7	118.91 (15)
C3—C2—C5	120.00 (15)	C12—C11—C10	120.21 (16)
C4—C3—C2	120.79 (16)	C12—C11—H11A	119.9
C4—C3—H3A	119.6	C10—C11—H11A	119.9
C2—C3—H3A	119.6	C11—C12—C5	121.83 (16)
C3^i—C4—C3	120.1 (2)	C11—C12—H12A	119.1
C3^i—C4—H4A	120.0	C5—C12—H12A	119.1
C3—C4—H4A	120.0	C8—C13—H13A	109.5
C6—C5—C12	118.32 (15)	C8—C13—H13B	109.5
C6—C5—C2	122.17 (16)	H13A—C13—H13B	109.5
C12—C5—C2	119.51 (16)	C8—C13—H13C	109.5
C5—C6—C7	120.66 (16)	H13A—C13—H13C	109.5
C5—C6—H6A	119.7	H13B—C13—H13C	109.5
C7—C6—H6A	119.7	C9—C14—H14A	109.5
N1—C7—C6	119.33 (16)	C9—C14—H14B	109.5
N1—C7—C10	120.71 (15)	H14A—C14—H14B	109.5
C6—C7—C10	119.96 (16)	C9—C14—H14C	109.5
N1—C8—C9	122.28 (16)	H14A—C14—H14C	109.5
N1—C8—C13	117.71 (16)	H14B—C14—H14C	109.5
C2^i—C1—C2—C3	−0.93 (12)	C10—N2—C9—C8	−2.2 (2)
C2^i—C1—C2—C5	179.81 (18)	C10—N2—C9—C14	177.32 (15)
C1—C2—C3—C4	1.9 (2)	N1—C8—C9—N2	3.1 (3)
C5—C2—C3—C4	−178.83 (14)	C13—C8—C9—N2	−176.95 (15)
C2—C3—C4—C3^i	−0.97 (12)	N1—C8—C9—C14	−176.41 (16)
C1—C2—C5—C6	−39.8 (2)	C13—C8—C9—C14	3.5 (2)
C3—C2—C5—C6	140.92 (18)	C9—N2—C10—C11	−178.64 (15)
C1—C2—C5—C12	139.70 (15)	C9—N2—C10—C7	−1.4 (2)
C3—C2—C5—C12	−39.6 (3)	N1—C7—C10—N2	4.6 (3)
C12—C5—C6—C7	−3.0 (3)	C6—C7—C10—N2	−175.09 (15)
C2—C5—C6—C7	176.57 (15)	N1—C7—C10—C11	−178.22 (14)
C8—N1—C7—C6	176.03 (15)	C6—C7—C10—C11	2.1 (3)
C8—N1—C7—C10	−3.6 (2)	N2—C10—C11—C12	175.60 (15)
C5—C6—C7—N1	−179.42 (15)	C7—C10—C11—C12	−1.7 (3)
C5—C6—C7—C10	0.2 (3)	C10—C11—C12—C5	−1.1 (3)
C7—N1—C8—C9	0.0 (2)	C6—C5—C12—C11	3.5 (3)
C7—N1—C8—C13	−179.94 (14)	C2—C5—C12—C11	−176.07 (15)

Symmetry code: (i) −x+1, y, −z+1/2.