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In the 2:1 cocrystal of quinoxaline with hydro­quinone, 2C8H6N2·C6H6O2, the phenolic mol­ecule is located on an inversion centre. It is connected via O—H...N inter­actions to two mol­ecules of the heterobase, forming discrete hydrogen-bonded assemblies. Quinoxaline mol­ecules are arranged into stacks by π–π face-to-face inter­actions whereas the hydro­quinone mol­ecules occupy channels formed between these stacks.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806028455/cs2015sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806028455/cs2015Isup2.hkl
Contains datablock I

CCDC reference: 618177

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.045
  • wR factor = 0.112
  • Data-to-parameter ratio = 12.4

checkCIF/PLATON results

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Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 6
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989) and Mercury (Version 1.4; Bruno et al., 2002); software used to prepare material for publication: SHELXL97.

quinoxaline–benzene-1,4-diol (2/1) top
Crystal data top
2C8H6N2·C6H6O2Z = 1
Mr = 370.40F(000) = 194
Triclinic, P1Dx = 1.385 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.0724 (9) ÅCell parameters from 1855 reflections
b = 7.2096 (10) Åθ = 4–25°
c = 9.1803 (12) ŵ = 0.09 mm1
α = 72.204 (12)°T = 100 K
β = 88.516 (11)°Plate, colourless
γ = 85.046 (11)°0.40 × 0.40 × 0.15 mm
V = 444.03 (10) Å3
Data collection top
Kuma KM-4-CCD κ-geometry
diffractometer
1258 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.043
Graphite monochromatorθmax = 25.0°, θmin = 2.3°
ω scansh = 85
3360 measured reflectionsk = 88
1573 independent reflectionsl = 1010
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)] = 0.045Hydrogen site location: difference Fourier map
wR(F2) = 0.112H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0598P)2 + 0.0086P]
where P = (Fo2 + 2Fc2)/3
1573 reflections(Δ/σ)max < 0.001
127 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.25 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
O10.21133 (16)0.81756 (16)0.87081 (13)0.0198 (3)
H1O0.29230.78820.80970.024*
C10.1082 (2)0.6586 (2)0.93286 (19)0.0162 (4)
C20.1304 (2)0.4913 (2)0.88608 (19)0.0167 (4)
H20.21670.48490.80500.020*
C30.0237 (2)0.3337 (2)0.95312 (19)0.0177 (4)
H30.04110.22050.91850.021*
N1A0.48166 (18)0.72676 (19)0.66305 (15)0.0177 (4)
C2A0.6570 (2)0.6492 (2)0.6950 (2)0.0192 (4)
H2AA0.69900.61010.79820.023*
C3A0.7858 (2)0.6221 (2)0.58003 (19)0.0193 (4)
H3AA0.90920.56160.61050.023*
N4A0.74228 (19)0.6766 (2)0.43385 (16)0.0194 (4)
C5A0.5012 (2)0.8216 (2)0.24289 (19)0.0189 (4)
H5AA0.58890.81180.16490.023*
C6A0.3179 (2)0.8960 (2)0.2051 (2)0.0202 (4)
H6AA0.27920.93730.10100.024*
C7A0.1860 (2)0.9118 (2)0.3200 (2)0.0205 (4)
H7AA0.05860.96080.29260.025*
C8A0.2400 (2)0.8574 (2)0.4702 (2)0.0185 (4)
H8AA0.15120.87140.54640.022*
C9A0.4283 (2)0.7801 (2)0.51173 (19)0.0158 (4)
C10A0.5600 (2)0.7595 (2)0.3973 (2)0.0166 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0206 (6)0.0202 (7)0.0199 (7)0.0029 (5)0.0064 (5)0.0082 (5)
C10.0141 (8)0.0176 (9)0.0154 (9)0.0004 (7)0.0026 (7)0.0028 (7)
C20.0146 (8)0.0218 (9)0.0137 (9)0.0025 (7)0.0011 (7)0.0065 (7)
C30.0184 (9)0.0181 (9)0.0179 (9)0.0014 (7)0.0012 (7)0.0084 (7)
N1A0.0189 (8)0.0168 (7)0.0181 (8)0.0043 (6)0.0017 (6)0.0057 (6)
C2A0.0219 (9)0.0167 (9)0.0187 (10)0.0031 (7)0.0018 (7)0.0043 (7)
C3A0.0164 (9)0.0198 (9)0.0223 (10)0.0009 (7)0.0013 (7)0.0075 (8)
N4A0.0178 (8)0.0190 (7)0.0223 (8)0.0009 (6)0.0018 (6)0.0077 (6)
C5A0.0220 (9)0.0174 (9)0.0189 (10)0.0015 (7)0.0043 (7)0.0083 (7)
C6A0.0248 (9)0.0182 (9)0.0174 (9)0.0022 (7)0.0022 (7)0.0049 (7)
C7A0.0166 (9)0.0168 (9)0.0269 (10)0.0010 (7)0.0026 (7)0.0051 (8)
C8A0.0177 (9)0.0162 (8)0.0236 (10)0.0019 (7)0.0052 (7)0.0094 (7)
C9A0.0188 (9)0.0107 (8)0.0185 (9)0.0039 (7)0.0020 (7)0.0047 (7)
C10A0.0170 (9)0.0119 (8)0.0216 (9)0.0021 (7)0.0017 (7)0.0061 (7)
Geometric parameters (Å, º) top
O1—C11.3761 (19)C3A—H3AA0.9500
O1—H1O0.8500N4A—C10A1.378 (2)
C1—C21.394 (2)C5A—C6A1.370 (2)
C1—C3i1.395 (2)C5A—C10A1.412 (2)
C2—C31.392 (2)C5A—H5AA0.9500
C2—H20.9600C6A—C7A1.415 (3)
C3—C1i1.395 (2)C6A—H6AA0.9500
C3—H30.9599C7A—C8A1.368 (2)
N1A—C2A1.318 (2)C7A—H7AA0.9500
N1A—C9A1.377 (2)C8A—C9A1.414 (2)
C2A—C3A1.423 (2)C8A—H8AA0.9500
C2A—H2AA0.9500C9A—C10A1.419 (2)
C3A—N4A1.315 (2)
C1—O1—H1O107.9C6A—C5A—C10A120.21 (16)
O1—C1—C2122.61 (15)C6A—C5A—H5AA119.9
O1—C1—C3i118.35 (15)C10A—C5A—H5AA119.9
C2—C1—C3i119.04 (15)C5A—C6A—C7A120.47 (16)
C3—C2—C1120.48 (15)C5A—C6A—H6AA119.8
C3—C2—H2119.0C7A—C6A—H6AA119.8
C1—C2—H2120.5C8A—C7A—C6A120.68 (15)
C2—C3—C1i120.48 (16)C8A—C7A—H7AA119.7
C2—C3—H3118.9C6A—C7A—H7AA119.7
C1i—C3—H3120.6C7A—C8A—C9A119.77 (16)
C2A—N1A—C9A116.38 (14)C7A—C8A—H8AA120.1
N1A—C2A—C3A122.24 (15)C9A—C8A—H8AA120.1
N1A—C2A—H2AA118.9N1A—C9A—C8A119.35 (15)
C3A—C2A—H2AA118.9N1A—C9A—C10A120.88 (14)
N4A—C3A—C2A123.23 (15)C8A—C9A—C10A119.77 (15)
N4A—C3A—H3AA118.4N4A—C10A—C5A119.37 (15)
C2A—C3A—H3AA118.4N4A—C10A—C9A121.54 (15)
C3A—N4A—C10A115.63 (15)C5A—C10A—C9A119.07 (15)
Symmetry code: (i) x, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···N1A0.851.992.8425 (18)179
C7A—H7AA···O1ii0.952.573.463 (2)157
C6A—H6AA···O1iii0.952.583.400 (2)144
Symmetry codes: (ii) x, y+2, z+1; (iii) x, y, z1.
 

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