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When recrystallized from ethanol, the title compound, C36H22N8, crystallized in the monoclinic space group P21/n, with the mol­ecule located on an inversion center. The quinoxaline moiety is approximately planar and is coplanar with the symmetry-related moiety in the mol­ecule. The two pyridine substituents lie out of the plane of the quinoxaline moiety by 40.1 (1) and 42.3 (1)°. They are inclined to one another by 56.8 (2)°, with their N atoms on opposite sides of the mean plane through the quinoxaline moiety.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803026977/na6273sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803026977/na6273Isup2.hkl
Contains datablock I

CCDC reference: 227921

Key indicators

  • Single-crystal X-ray study
  • T = 223 K
  • R factor = 0.042
  • wR factor = 0.096
  • Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 37 Perc.
Alert level C GOODF01_ALERT_2_C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.725 RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.132 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.13 PLAT480_ALERT_4_C Long H...A H-Bond Reported H12 .. C1G = 2.81 Ang. PLAT716_ALERT_1_C H...A Unknown or Inconsistent Label .......... C1G H12 C1G PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... C1G C12 C1G PLAT718_ALERT_1_C D-H..A Unknown or Inconsistent Label .......... C1G C12 H12 C1G
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: EXPOSE (Stoe, 2000); cell refinement: CELL (Stoe, 2000); data reduction: INTEGRATE (Stoe, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON99 (Spek, 1990); software used to prepare material for publication: SHELXL97.

2,3,2',3'-tetrakis(2-pyridyl)-6,6'-biquinoxalinyl top
Crystal data top
C36H22N8F(000) = 588
Mr = 566.62Dx = 1.325 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2327 reflections
a = 6.8892 (6) Åθ = 2.3–25.9°
b = 7.7255 (6) ŵ = 0.08 mm1
c = 26.895 (2) ÅT = 223 K
β = 97.024 (11)°Plate, orange
V = 1420.7 (2) Å30.35 × 0.30 × 0.10 mm
Z = 2
Data collection top
STOE IPDS
diffractometer
1024 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.133
Graphite monochromatorθmax = 25.9°, θmin = 2.7°
Detector resolution: 0.81Å pixels mm-1h = 88
φ oscillation scansk = 99
10763 measured reflectionsl = 3233
2771 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H-atom parameters constrained
S = 0.73 w = 1/[σ2(Fo2) + (0.0319P)2]
where P = (Fo2 + 2Fc2)/3
2771 reflections(Δ/σ)max < 0.001
199 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = 0.16 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.0978 (3)0.4588 (3)0.00588 (9)0.0391 (6)
C20.2028 (3)0.4709 (3)0.05264 (9)0.0419 (7)
H20.15140.53530.07770.050*
C30.3844 (3)0.3894 (3)0.06381 (8)0.0386 (6)
C40.6583 (4)0.3353 (4)0.11898 (8)0.0437 (7)
C50.7861 (4)0.3882 (4)0.16548 (9)0.0482 (7)
C60.7130 (4)0.4224 (4)0.20948 (10)0.0667 (9)
H60.57870.40970.21180.080*
C70.8399 (5)0.4762 (5)0.25066 (11)0.0813 (11)
H70.79410.49840.28160.098*
C81.0331 (6)0.4958 (5)0.24508 (12)0.0829 (11)
H81.12320.53190.27220.099*
C91.0935 (5)0.4622 (5)0.19948 (12)0.0761 (10)
H91.22650.47730.19600.091*
C100.7227 (4)0.2137 (4)0.08426 (9)0.0428 (7)
C110.8921 (4)0.0958 (4)0.09789 (9)0.0451 (7)
C121.0261 (4)0.0629 (4)0.06535 (9)0.0484 (7)
H121.01250.11430.03340.058*
C131.1805 (4)0.0458 (4)0.07982 (12)0.0623 (9)
H131.27640.06710.05850.075*
C141.1914 (5)0.1225 (4)0.12600 (12)0.0708 (10)
H141.29530.19720.13730.085*
C151.0480 (5)0.0878 (5)0.15514 (11)0.0752 (10)
H151.05470.14410.18630.090*
C160.4602 (4)0.2882 (3)0.02761 (9)0.0389 (6)
C170.3557 (4)0.2787 (4)0.02080 (9)0.0460 (7)
H170.40610.21450.04600.055*
C180.1821 (4)0.3625 (4)0.03095 (9)0.0442 (7)
H180.11540.35640.06360.053*
N10.4891 (3)0.4161 (3)0.11010 (7)0.0460 (6)
N20.6291 (3)0.1949 (3)0.03847 (7)0.0450 (6)
N30.9736 (3)0.4090 (3)0.15973 (8)0.0611 (7)
N40.8983 (3)0.0200 (3)0.14284 (8)0.0639 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0349 (14)0.0432 (17)0.0390 (14)0.0000 (13)0.0040 (11)0.0013 (12)
C20.0390 (15)0.0474 (19)0.0396 (14)0.0056 (14)0.0065 (12)0.0041 (13)
C30.0355 (15)0.0437 (17)0.0364 (13)0.0001 (14)0.0029 (11)0.0000 (13)
C40.0386 (16)0.0561 (19)0.0368 (13)0.0059 (15)0.0063 (12)0.0002 (13)
C50.0412 (16)0.060 (2)0.0423 (15)0.0094 (15)0.0008 (12)0.0025 (14)
C60.0536 (18)0.098 (3)0.0498 (17)0.0084 (19)0.0107 (15)0.0113 (17)
C70.083 (2)0.113 (3)0.0485 (18)0.008 (2)0.0073 (18)0.0163 (19)
C80.080 (3)0.104 (3)0.057 (2)0.009 (2)0.0206 (19)0.010 (2)
C90.0503 (18)0.102 (3)0.073 (2)0.004 (2)0.0071 (17)0.011 (2)
C100.0373 (15)0.0475 (18)0.0446 (15)0.0026 (14)0.0090 (13)0.0036 (14)
C110.0411 (15)0.0487 (19)0.0444 (15)0.0046 (15)0.0009 (13)0.0000 (14)
C120.0455 (16)0.048 (2)0.0523 (15)0.0043 (16)0.0092 (13)0.0016 (14)
C130.0504 (19)0.058 (2)0.080 (2)0.0107 (18)0.0140 (16)0.0104 (18)
C140.064 (2)0.068 (2)0.076 (2)0.0267 (19)0.0114 (19)0.0063 (19)
C150.090 (3)0.081 (3)0.0525 (18)0.030 (2)0.0016 (18)0.0119 (18)
C160.0350 (15)0.0418 (17)0.0403 (14)0.0025 (14)0.0058 (12)0.0015 (13)
C170.0407 (17)0.056 (2)0.0403 (15)0.0053 (15)0.0024 (13)0.0072 (13)
C180.0364 (15)0.056 (2)0.0394 (14)0.0011 (15)0.0021 (12)0.0058 (14)
N10.0386 (13)0.0571 (17)0.0421 (12)0.0076 (12)0.0038 (10)0.0030 (11)
N20.0419 (14)0.0500 (16)0.0425 (12)0.0044 (12)0.0027 (10)0.0035 (11)
N30.0442 (14)0.086 (2)0.0521 (14)0.0009 (15)0.0017 (11)0.0083 (14)
N40.0683 (17)0.0724 (19)0.0514 (14)0.0244 (16)0.0084 (12)0.0103 (13)
Geometric parameters (Å, º) top
C1—C21.375 (3)C9—H90.9400
C1—C181.419 (3)C10—N21.326 (3)
C1—C1i1.488 (5)C10—C111.491 (3)
C2—C31.400 (3)C11—N41.339 (3)
C2—H20.9400C11—C121.371 (3)
C3—N11.376 (3)C12—C131.374 (4)
C3—C161.399 (3)C12—H120.9400
C4—N11.318 (3)C13—C141.370 (4)
C4—C101.432 (3)C13—H130.9400
C4—C51.496 (3)C14—C151.361 (4)
C5—N31.330 (3)C14—H140.9400
C5—C61.367 (4)C15—N41.335 (4)
C6—C71.388 (4)C15—H150.9400
C6—H60.9400C16—N21.370 (3)
C7—C81.366 (4)C16—C171.410 (3)
C7—H70.9400C17—C181.358 (3)
C8—C91.367 (4)C17—H170.9400
C8—H80.9400C18—H180.9400
C9—N31.333 (3)
C2—C1—C18117.3 (2)C4—C10—C11122.4 (2)
C2—C1—C1i121.8 (3)N4—C11—C12123.1 (2)
C18—C1—C1i120.9 (3)N4—C11—C10115.3 (2)
C1—C2—C3121.5 (2)C12—C11—C10121.6 (2)
C1—C2—H2119.3C11—C12—C13119.4 (3)
C3—C2—H2119.3C11—C12—H12120.3
N1—C3—C16121.0 (2)C13—C12—H12120.3
N1—C3—C2118.9 (2)C14—C13—C12118.5 (3)
C16—C3—C2120.1 (2)C14—C13—H13120.8
N1—C4—C10122.0 (2)C12—C13—H13120.8
N1—C4—C5116.0 (2)C15—C14—C13118.3 (3)
C10—C4—C5121.8 (2)C15—C14—H14120.9
N3—C5—C6122.9 (2)C13—C14—H14120.9
N3—C5—C4114.6 (2)N4—C15—C14125.0 (3)
C6—C5—C4122.3 (2)N4—C15—H15117.5
C5—C6—C7119.1 (3)C14—C15—H15117.5
C5—C6—H6120.5N2—C16—C3121.7 (2)
C7—C6—H6120.5N2—C16—C17119.6 (2)
C8—C7—C6118.2 (3)C3—C16—C17118.7 (2)
C8—C7—H7120.9C18—C17—C16119.9 (3)
C6—C7—H7120.9C18—C17—H17120.1
C7—C8—C9119.0 (3)C16—C17—H17120.1
C7—C8—H8120.5C17—C18—C1122.4 (2)
C9—C8—H8120.5C17—C18—H18118.8
N3—C9—C8123.4 (3)C1—C18—H18118.8
N3—C9—H9118.3C4—N1—C3116.6 (2)
C8—C9—H9118.3C10—N2—C16116.4 (2)
N2—C10—C4121.5 (2)C5—N3—C9117.3 (2)
N2—C10—C11116.0 (2)C15—N4—C11115.8 (2)
C18—C1—C2—C30.9 (4)C13—C14—C15—N42.0 (5)
C1i—C1—C2—C3178.3 (3)N1—C3—C16—N28.0 (4)
C1—C2—C3—N1175.4 (2)C2—C3—C16—N2174.4 (2)
C1—C2—C3—C162.2 (4)N1—C3—C16—C17173.9 (3)
N1—C4—C5—N3136.2 (3)C2—C3—C16—C173.7 (4)
C10—C4—C5—N339.1 (4)N2—C16—C17—C18176.0 (2)
N1—C4—C5—C640.1 (4)C3—C16—C17—C182.1 (4)
C10—C4—C5—C6144.6 (3)C16—C17—C18—C11.0 (4)
N3—C5—C6—C72.0 (5)C2—C1—C18—C172.6 (4)
C4—C5—C6—C7178.0 (3)C1i—C1—C18—C17176.7 (3)
C5—C6—C7—C81.2 (5)C10—C4—N1—C35.4 (4)
C6—C7—C8—C90.0 (6)C5—C4—N1—C3169.9 (2)
C7—C8—C9—N30.7 (6)C16—C3—N1—C43.1 (4)
N1—C4—C10—N29.8 (4)C2—C3—N1—C4179.4 (2)
C5—C4—C10—N2165.2 (2)C4—C10—N2—C164.7 (4)
N1—C4—C10—C11167.3 (3)C11—C10—N2—C16172.6 (2)
C5—C4—C10—C1117.7 (4)C3—C16—N2—C103.8 (4)
N2—C10—C11—N4133.7 (3)C17—C16—N2—C10178.1 (3)
C4—C10—C11—N443.6 (4)C6—C5—N3—C91.4 (5)
N2—C10—C11—C1243.7 (4)C4—C5—N3—C9177.7 (3)
C4—C10—C11—C12139.0 (3)C8—C9—N3—C50.0 (5)
N4—C11—C12—C133.3 (4)C14—C15—N4—C110.9 (5)
C10—C11—C12—C13179.5 (3)C12—C11—N4—C151.8 (4)
C11—C12—C13—C142.1 (4)C10—C11—N4—C15179.1 (3)
C12—C13—C14—C150.4 (5)
Symmetry code: (i) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···N4ii0.942.563.487 (4)167
C12—H12···C1giii0.942.813.343 (3)117
Symmetry codes: (ii) x+3/2, y+1/2, z+1/2; (iii) x+1, y, z.
 

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