In the title complex, benzene-1,3,5-tricarboxylic acid–pyrazine
N,
N′-dioxide (2/1), C
9H
6O
6·0.5C
4H
4N
2O
2, 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
CCDC reference: 942551
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
C9H6O6·0.5C4H4N2O2 | F(000) = 274 |
Mr = 266.18 | centrosymmetric |
Triclinic, P1 | Dx = 1.665 Mg m−3 |
a = 7.9521 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.0939 (2) Å | Cell parameters from 5692 reflections |
c = 8.6271 (2) Å | θ = 2.4–37.4° |
α = 78.621 (1)° | µ = 0.14 mm−1 |
β = 80.700 (1)° | T = 105 K |
γ = 79.769 (1)° | Block, colourless |
V = 531.07 (2) Å3 | 0.90 × 0.55 × 0.28 mm |
Z = 2 | |
Data collection top
Bruker APEXII CCD area-detector diffractometer | 5615 independent reflections |
Radiation source: fine-focus sealed tube | 4246 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.011 |
Detector resolution: 8.3 pixels mm-1 | θmax = 37.6°, θmin = 2.4° |
phi and ω scans | h = −13→13 |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | k = −13→9 |
Tmin = 0.910, Tmax = 0.961 | l = −14→14 |
8828 measured reflections | |
Refinement top
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | All 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 parameters | Δρmax = 0.60 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.20981 (6) | 0.51187 (6) | 0.45416 (6) | 0.01528 (9) | |
H1 | 0.145 (2) | 0.574 (2) | 0.376 (2) | 0.048 (4)* | |
O2 | 0.34003 (7) | 0.40854 (8) | 0.23656 (6) | 0.02106 (11) | |
O3 | 0.86133 (7) | −0.02322 (7) | 0.28510 (6) | 0.01846 (10) | |
H3 | 0.925 (2) | −0.124 (2) | 0.2599 (19) | 0.044 (4)* | |
O4 | 0.91678 (6) | −0.16621 (6) | 0.52724 (6) | 0.01699 (10) | |
O5 | 0.39074 (8) | 0.30350 (9) | 0.96259 (7) | 0.02744 (13) | |
H5 | 0.394 (3) | 0.318 (2) | 1.066 (2) | 0.061 (5)* | |
O6 | 0.64278 (8) | 0.13485 (8) | 0.99820 (7) | 0.02502 (12) | |
C1 | 0.45276 (7) | 0.29798 (7) | 0.48226 (7) | 0.01228 (10) | |
C2 | 0.58822 (8) | 0.18875 (8) | 0.41343 (7) | 0.01300 (10) | |
H21 | 0.5998 (16) | 0.1842 (16) | 0.2972 (15) | 0.020 (3)* | |
C3 | 0.70115 (8) | 0.08024 (7) | 0.51068 (7) | 0.01255 (10) | |
C4 | 0.68177 (8) | 0.08335 (8) | 0.67383 (8) | 0.01434 (11) | |
H41 | 0.7613 (16) | 0.0065 (15) | 0.7433 (14) | 0.021 (3)* | |
C5 | 0.54824 (8) | 0.19486 (8) | 0.74090 (7) | 0.01400 (10) | |
C6 | 0.43213 (8) | 0.30052 (8) | 0.64503 (7) | 0.01384 (10) | |
H61 | 0.3369 (16) | 0.3745 (16) | 0.6957 (15) | 0.022 (3)* | |
C7 | 0.32978 (8) | 0.40975 (8) | 0.37898 (7) | 0.01312 (10) | |
C8 | 0.83793 (8) | −0.04822 (8) | 0.44402 (8) | 0.01324 (10) | |
C9 | 0.53451 (9) | 0.20538 (9) | 0.91312 (8) | 0.01750 (12) | |
O7 | 0.02426 (7) | 0.67750 (7) | 0.22425 (6) | 0.01941 (11) | |
C10 | 0.04339 (9) | 0.65945 (8) | −0.04215 (8) | 0.01675 (11) | |
H10 | 0.0772 (16) | 0.7677 (16) | −0.0657 (15) | 0.023 (3)* | |
C11 | −0.02925 (9) | 0.43131 (8) | 0.15687 (8) | 0.01661 (11) | |
H11 | −0.0446 (18) | 0.3884 (17) | 0.2701 (16) | 0.030 (3)* | |
N1 | 0.01283 (7) | 0.59084 (7) | 0.11436 (7) | 0.01432 (10) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.01576 (19) | 0.01560 (19) | 0.01361 (19) | 0.00386 (15) | −0.00370 (15) | −0.00459 (16) |
O2 | 0.0241 (2) | 0.0254 (3) | 0.0122 (2) | 0.00680 (19) | −0.00556 (17) | −0.00653 (18) |
O3 | 0.0223 (2) | 0.0168 (2) | 0.0144 (2) | 0.00525 (17) | −0.00298 (17) | −0.00514 (17) |
O4 | 0.0174 (2) | 0.01338 (19) | 0.0196 (2) | 0.00125 (15) | −0.00611 (17) | −0.00172 (17) |
O5 | 0.0265 (3) | 0.0396 (3) | 0.0145 (2) | 0.0101 (2) | −0.00541 (19) | −0.0121 (2) |
O6 | 0.0251 (3) | 0.0332 (3) | 0.0159 (2) | 0.0034 (2) | −0.00896 (19) | −0.0043 (2) |
C1 | 0.0126 (2) | 0.0126 (2) | 0.0117 (2) | 0.00001 (17) | −0.00300 (17) | −0.00288 (18) |
C2 | 0.0132 (2) | 0.0129 (2) | 0.0129 (2) | −0.00027 (17) | −0.00269 (18) | −0.00302 (18) |
C3 | 0.0124 (2) | 0.0119 (2) | 0.0134 (2) | −0.00016 (17) | −0.00250 (17) | −0.00318 (18) |
C4 | 0.0145 (2) | 0.0148 (2) | 0.0137 (2) | −0.00043 (18) | −0.00394 (19) | −0.00254 (19) |
C5 | 0.0148 (2) | 0.0161 (2) | 0.0113 (2) | −0.00082 (18) | −0.00300 (18) | −0.00311 (19) |
C6 | 0.0139 (2) | 0.0154 (2) | 0.0123 (2) | −0.00010 (18) | −0.00253 (18) | −0.00369 (19) |
C7 | 0.0138 (2) | 0.0135 (2) | 0.0121 (2) | 0.00009 (17) | −0.00286 (18) | −0.00346 (18) |
C8 | 0.0131 (2) | 0.0119 (2) | 0.0153 (2) | −0.00086 (17) | −0.00338 (18) | −0.00344 (19) |
C9 | 0.0187 (3) | 0.0210 (3) | 0.0128 (2) | −0.0004 (2) | −0.0034 (2) | −0.0038 (2) |
O7 | 0.0259 (2) | 0.0169 (2) | 0.0166 (2) | 0.00530 (17) | −0.00877 (18) | −0.00859 (17) |
C10 | 0.0210 (3) | 0.0147 (2) | 0.0144 (2) | −0.0016 (2) | −0.0042 (2) | −0.0015 (2) |
C11 | 0.0206 (3) | 0.0156 (2) | 0.0128 (2) | −0.0008 (2) | −0.0030 (2) | −0.0015 (2) |
N1 | 0.0159 (2) | 0.0141 (2) | 0.0128 (2) | 0.00247 (16) | −0.00431 (16) | −0.00424 (17) |
Geometric parameters (Å, º) top
O1—C7 | 1.3212 (8) | C3—C4 | 1.3957 (9) |
O1—H1 | 0.928 (18) | C3—C8 | 1.4923 (8) |
O2—C7 | 1.2200 (8) | C4—C5 | 1.3942 (9) |
O3—C8 | 1.3330 (8) | C4—H41 | 0.991 (13) |
O3—H3 | 0.929 (17) | C5—C6 | 1.3982 (9) |
O4—C8 | 1.2177 (8) | C5—C9 | 1.4902 (9) |
O5—C9 | 1.3318 (9) | C6—H61 | 0.979 (13) |
O5—H5 | 0.931 (19) | O7—N1 | 1.3083 (7) |
O6—C9 | 1.2125 (9) | C10—N1 | 1.3552 (9) |
C1—C6 | 1.3910 (9) | C10—C11i | 1.3727 (10) |
C1—C2 | 1.3988 (8) | C10—H10 | 0.937 (13) |
C1—C7 | 1.4893 (8) | C11—N1 | 1.3567 (9) |
C2—C3 | 1.3980 (8) | C11—C10i | 1.3727 (10) |
C2—H21 | 0.999 (12) | C11—H11 | 0.965 (14) |
| | | |
C7—O1—H1 | 104.8 (10) | C5—C6—H61 | 118.3 (7) |
C8—O3—H3 | 104.6 (10) | O2—C7—O1 | 122.79 (6) |
C9—O5—H5 | 109.4 (13) | O2—C7—C1 | 122.86 (6) |
C6—C1—C2 | 120.45 (6) | O1—C7—C1 | 114.35 (5) |
C6—C1—C7 | 120.56 (5) | O4—C8—O3 | 123.68 (6) |
C2—C1—C7 | 118.98 (5) | O4—C8—C3 | 123.04 (6) |
C3—C2—C1 | 119.16 (6) | O3—C8—C3 | 113.25 (5) |
C3—C2—H21 | 120.7 (7) | O6—C9—O5 | 123.72 (7) |
C1—C2—H21 | 120.1 (7) | O6—C9—C5 | 124.02 (6) |
C4—C3—C2 | 120.56 (6) | O5—C9—C5 | 112.26 (6) |
C4—C3—C8 | 118.69 (5) | N1—C10—C11i | 120.04 (6) |
C2—C3—C8 | 120.65 (6) | N1—C10—H10 | 116.6 (8) |
C5—C4—C3 | 119.86 (6) | C11i—C10—H10 | 123.3 (8) |
C5—C4—H41 | 119.3 (7) | N1—C11—C10i | 120.26 (6) |
C3—C4—H41 | 120.8 (7) | N1—C11—H11 | 115.4 (8) |
C4—C5—C6 | 119.85 (6) | C10i—C11—H11 | 124.3 (8) |
C4—C5—C9 | 119.65 (6) | O7—N1—C10 | 120.30 (6) |
C6—C5—C9 | 120.45 (6) | O7—N1—C11 | 120.00 (6) |
C1—C6—C5 | 120.07 (6) | C10—N1—C11 | 119.69 (6) |
C1—C6—H61 | 121.6 (7) | | |
| | | |
C6—C1—C2—C3 | 0.96 (9) | C6—C1—C7—O1 | 2.80 (9) |
C7—C1—C2—C3 | −178.25 (5) | C2—C1—C7—O1 | −177.99 (5) |
C1—C2—C3—C4 | −1.49 (9) | C4—C3—C8—O4 | 11.04 (9) |
C1—C2—C3—C8 | 174.80 (5) | C2—C3—C8—O4 | −165.32 (6) |
C2—C3—C4—C5 | 0.34 (9) | C4—C3—C8—O3 | −170.67 (6) |
C8—C3—C4—C5 | −176.03 (5) | C2—C3—C8—O3 | 12.97 (8) |
C3—C4—C5—C6 | 1.35 (9) | C4—C5—C9—O6 | 7.68 (11) |
C3—C4—C5—C9 | −176.25 (6) | C6—C5—C9—O6 | −169.91 (7) |
C2—C1—C6—C5 | 0.71 (9) | C4—C5—C9—O5 | −173.32 (6) |
C7—C1—C6—C5 | 179.91 (6) | C6—C5—C9—O5 | 9.09 (10) |
C4—C5—C6—C1 | −1.87 (10) | C11i—C10—N1—O7 | −179.25 (6) |
C9—C5—C6—C1 | 175.71 (6) | C11i—C10—N1—C11 | 0.96 (11) |
C6—C1—C7—O2 | −177.97 (6) | C10i—C11—N1—O7 | 179.24 (6) |
C2—C1—C7—O2 | 1.24 (10) | C10i—C11—N1—C10 | −0.97 (11) |
Symmetry code: (i) −x, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O7 | 0.928 (18) | 1.739 (18) | 2.6651 (7) | 175.9 (16) |
O3—H3···O7ii | 0.929 (17) | 1.719 (17) | 2.6437 (7) | 173.6 (15) |
O5—H5···O2iii | 0.931 (19) | 1.73 (2) | 2.6144 (8) | 158.0 (19) |
C10—H10···O3iv | 0.937 (13) | 2.571 (13) | 3.3883 (8) | 145.9 (10) |
C11—H11···O4v | 0.965 (14) | 2.451 (14) | 3.2603 (8) | 141.2 (11) |
Symmetry codes: (ii) x+1, y−1, z; (iii) x, y, z+1; (iv) −x+1, −y+1, −z; (v) −x+1, −y, −z+1. |