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In the title complex, benzene-1,3,5-tri­carb­oxy­lic acid–pyrazine N,N′-dioxide (2/1), C9H6O6·0.5C4H4N2O2, cocrystallized trimesic acid (TMA) and pyrazine N,N′-dioxide (PNO) mol­ecules form strong O—H...O hydrogen bonds, but also important weak C—H...O and dipole–dipole inter­molecular inter­actions, to generate a densely packed three-dimensional network. PNO mol­ecules lie on inversion centres where they connect pairs of TMA sheets into distinct two-dimensional hydrogen-bonded layers perpendicular to the crystallographic ab diagonal.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229613032737/gz3247sup1.cif
Contains datablocks I, TMA-PNO

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229613032737/gz3247Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229613032737/gz3247Isup3.cml
Supplementary material

CCDC reference: 942551

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: APEX2 (Bruker, 2013); data reduction: APEX2 (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Benzene-1,3,5-tricarboxylic acid–pyrazine N,N'-dioxide (2/1) top
Crystal data top
C9H6O6·0.5C4H4N2O2F(000) = 274
Mr = 266.18centrosymmetric
Triclinic, P1Dx = 1.665 Mg m3
a = 7.9521 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.0939 (2) ÅCell parameters from 5692 reflections
c = 8.6271 (2) Åθ = 2.4–37.4°
α = 78.621 (1)°µ = 0.14 mm1
β = 80.700 (1)°T = 105 K
γ = 79.769 (1)°Block, colourless
V = 531.07 (2) Å30.90 × 0.55 × 0.28 mm
Z = 2
Data collection top
Bruker APEXII CCD area-detector
diffractometer
5615 independent reflections
Radiation source: fine-focus sealed tube4246 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.011
Detector resolution: 8.3 pixels mm-1θmax = 37.6°, θmin = 2.4°
phi and ω scansh = 1313
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
k = 139
Tmin = 0.910, Tmax = 0.961l = 1414
8828 measured 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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108All H-atom parameters refined
S = 1.03 w = 1/[σ2(Fo2) + (0.0677P)2 + 0.0833P]
where P = (Fo2 + 2Fc2)/3
4773 reflections(Δ/σ)max = 0.001
204 parametersΔρmax = 0.60 e Å3
0 restraintsΔρmin = 0.28 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
O10.20981 (6)0.51187 (6)0.45416 (6)0.01528 (9)
H10.145 (2)0.574 (2)0.376 (2)0.048 (4)*
O20.34003 (7)0.40854 (8)0.23656 (6)0.02106 (11)
O30.86133 (7)0.02322 (7)0.28510 (6)0.01846 (10)
H30.925 (2)0.124 (2)0.2599 (19)0.044 (4)*
O40.91678 (6)0.16621 (6)0.52724 (6)0.01699 (10)
O50.39074 (8)0.30350 (9)0.96259 (7)0.02744 (13)
H50.394 (3)0.318 (2)1.066 (2)0.061 (5)*
O60.64278 (8)0.13485 (8)0.99820 (7)0.02502 (12)
C10.45276 (7)0.29798 (7)0.48226 (7)0.01228 (10)
C20.58822 (8)0.18875 (8)0.41343 (7)0.01300 (10)
H210.5998 (16)0.1842 (16)0.2972 (15)0.020 (3)*
C30.70115 (8)0.08024 (7)0.51068 (7)0.01255 (10)
C40.68177 (8)0.08335 (8)0.67383 (8)0.01434 (11)
H410.7613 (16)0.0065 (15)0.7433 (14)0.021 (3)*
C50.54824 (8)0.19486 (8)0.74090 (7)0.01400 (10)
C60.43213 (8)0.30052 (8)0.64503 (7)0.01384 (10)
H610.3369 (16)0.3745 (16)0.6957 (15)0.022 (3)*
C70.32978 (8)0.40975 (8)0.37898 (7)0.01312 (10)
C80.83793 (8)0.04822 (8)0.44402 (8)0.01324 (10)
C90.53451 (9)0.20538 (9)0.91312 (8)0.01750 (12)
O70.02426 (7)0.67750 (7)0.22425 (6)0.01941 (11)
C100.04339 (9)0.65945 (8)0.04215 (8)0.01675 (11)
H100.0772 (16)0.7677 (16)0.0657 (15)0.023 (3)*
C110.02925 (9)0.43131 (8)0.15687 (8)0.01661 (11)
H110.0446 (18)0.3884 (17)0.2701 (16)0.030 (3)*
N10.01283 (7)0.59084 (7)0.11436 (7)0.01432 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.01576 (19)0.01560 (19)0.01361 (19)0.00386 (15)0.00370 (15)0.00459 (16)
O20.0241 (2)0.0254 (3)0.0122 (2)0.00680 (19)0.00556 (17)0.00653 (18)
O30.0223 (2)0.0168 (2)0.0144 (2)0.00525 (17)0.00298 (17)0.00514 (17)
O40.0174 (2)0.01338 (19)0.0196 (2)0.00125 (15)0.00611 (17)0.00172 (17)
O50.0265 (3)0.0396 (3)0.0145 (2)0.0101 (2)0.00541 (19)0.0121 (2)
O60.0251 (3)0.0332 (3)0.0159 (2)0.0034 (2)0.00896 (19)0.0043 (2)
C10.0126 (2)0.0126 (2)0.0117 (2)0.00001 (17)0.00300 (17)0.00288 (18)
C20.0132 (2)0.0129 (2)0.0129 (2)0.00027 (17)0.00269 (18)0.00302 (18)
C30.0124 (2)0.0119 (2)0.0134 (2)0.00016 (17)0.00250 (17)0.00318 (18)
C40.0145 (2)0.0148 (2)0.0137 (2)0.00043 (18)0.00394 (19)0.00254 (19)
C50.0148 (2)0.0161 (2)0.0113 (2)0.00082 (18)0.00300 (18)0.00311 (19)
C60.0139 (2)0.0154 (2)0.0123 (2)0.00010 (18)0.00253 (18)0.00369 (19)
C70.0138 (2)0.0135 (2)0.0121 (2)0.00009 (17)0.00286 (18)0.00346 (18)
C80.0131 (2)0.0119 (2)0.0153 (2)0.00086 (17)0.00338 (18)0.00344 (19)
C90.0187 (3)0.0210 (3)0.0128 (2)0.0004 (2)0.0034 (2)0.0038 (2)
O70.0259 (2)0.0169 (2)0.0166 (2)0.00530 (17)0.00877 (18)0.00859 (17)
C100.0210 (3)0.0147 (2)0.0144 (2)0.0016 (2)0.0042 (2)0.0015 (2)
C110.0206 (3)0.0156 (2)0.0128 (2)0.0008 (2)0.0030 (2)0.0015 (2)
N10.0159 (2)0.0141 (2)0.0128 (2)0.00247 (16)0.00431 (16)0.00424 (17)
Geometric parameters (Å, º) top
O1—C71.3212 (8)C3—C41.3957 (9)
O1—H10.928 (18)C3—C81.4923 (8)
O2—C71.2200 (8)C4—C51.3942 (9)
O3—C81.3330 (8)C4—H410.991 (13)
O3—H30.929 (17)C5—C61.3982 (9)
O4—C81.2177 (8)C5—C91.4902 (9)
O5—C91.3318 (9)C6—H610.979 (13)
O5—H50.931 (19)O7—N11.3083 (7)
O6—C91.2125 (9)C10—N11.3552 (9)
C1—C61.3910 (9)C10—C11i1.3727 (10)
C1—C21.3988 (8)C10—H100.937 (13)
C1—C71.4893 (8)C11—N11.3567 (9)
C2—C31.3980 (8)C11—C10i1.3727 (10)
C2—H210.999 (12)C11—H110.965 (14)
C7—O1—H1104.8 (10)C5—C6—H61118.3 (7)
C8—O3—H3104.6 (10)O2—C7—O1122.79 (6)
C9—O5—H5109.4 (13)O2—C7—C1122.86 (6)
C6—C1—C2120.45 (6)O1—C7—C1114.35 (5)
C6—C1—C7120.56 (5)O4—C8—O3123.68 (6)
C2—C1—C7118.98 (5)O4—C8—C3123.04 (6)
C3—C2—C1119.16 (6)O3—C8—C3113.25 (5)
C3—C2—H21120.7 (7)O6—C9—O5123.72 (7)
C1—C2—H21120.1 (7)O6—C9—C5124.02 (6)
C4—C3—C2120.56 (6)O5—C9—C5112.26 (6)
C4—C3—C8118.69 (5)N1—C10—C11i120.04 (6)
C2—C3—C8120.65 (6)N1—C10—H10116.6 (8)
C5—C4—C3119.86 (6)C11i—C10—H10123.3 (8)
C5—C4—H41119.3 (7)N1—C11—C10i120.26 (6)
C3—C4—H41120.8 (7)N1—C11—H11115.4 (8)
C4—C5—C6119.85 (6)C10i—C11—H11124.3 (8)
C4—C5—C9119.65 (6)O7—N1—C10120.30 (6)
C6—C5—C9120.45 (6)O7—N1—C11120.00 (6)
C1—C6—C5120.07 (6)C10—N1—C11119.69 (6)
C1—C6—H61121.6 (7)
C6—C1—C2—C30.96 (9)C6—C1—C7—O12.80 (9)
C7—C1—C2—C3178.25 (5)C2—C1—C7—O1177.99 (5)
C1—C2—C3—C41.49 (9)C4—C3—C8—O411.04 (9)
C1—C2—C3—C8174.80 (5)C2—C3—C8—O4165.32 (6)
C2—C3—C4—C50.34 (9)C4—C3—C8—O3170.67 (6)
C8—C3—C4—C5176.03 (5)C2—C3—C8—O312.97 (8)
C3—C4—C5—C61.35 (9)C4—C5—C9—O67.68 (11)
C3—C4—C5—C9176.25 (6)C6—C5—C9—O6169.91 (7)
C2—C1—C6—C50.71 (9)C4—C5—C9—O5173.32 (6)
C7—C1—C6—C5179.91 (6)C6—C5—C9—O59.09 (10)
C4—C5—C6—C11.87 (10)C11i—C10—N1—O7179.25 (6)
C9—C5—C6—C1175.71 (6)C11i—C10—N1—C110.96 (11)
C6—C1—C7—O2177.97 (6)C10i—C11—N1—O7179.24 (6)
C2—C1—C7—O21.24 (10)C10i—C11—N1—C100.97 (11)
Symmetry code: (i) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O70.928 (18)1.739 (18)2.6651 (7)175.9 (16)
O3—H3···O7ii0.929 (17)1.719 (17)2.6437 (7)173.6 (15)
O5—H5···O2iii0.931 (19)1.73 (2)2.6144 (8)158.0 (19)
C10—H10···O3iv0.937 (13)2.571 (13)3.3883 (8)145.9 (10)
C11—H11···O4v0.965 (14)2.451 (14)3.2603 (8)141.2 (11)
Symmetry codes: (ii) x+1, y1, z; (iii) x, y, z+1; (iv) x+1, y+1, z; (v) x+1, y, z+1.
 

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