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In the title compound, C10H8N8·C8H6O4, both acid and base mol­ecules (A:B) have twofold crystallographic symmetry. One-dimensional zigzag chains of rings form as (A...B...)n through O—H...N and C—H...O=C inter­actions; further association of B (with A) along the a axis via bifurcated N—H...N and π–π stacking inter­actions gives a three-dimensional self-penetrating structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806039894/gg2015sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806039894/gg2015Isup2.hkl
Contains datablock I

CCDC reference: 629305

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.040
  • wR factor = 0.098
  • Data-to-parameter ratio = 10.8

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.764 1.000 Tmin(prime) and Tmax expected: 0.962 0.993 RR(prime) = 0.788 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.79 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C8 H6 O4
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 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

Computing details top

Data collection: SMART-NT (Bruker, 1998); cell refinement: SMART-NT; data reduction: SAINT-NT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL-NT (Bruker, 1998).

1,4-Dihydro-3,6-dipyrazin-2-yl-1,2,4,5-tetrazine–benzene-1,3-dicarboxylic acid (1/1) top
Crystal data top
C10H8N8·C8H6O4F(000) = 840
Mr = 406.37Dx = 1.599 Mg m3
Orthorhombic, PnnaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2a 2bcCell parameters from 650 reflections
a = 13.546 (4) Åθ = 3.0–19.8°
b = 33.654 (11) ŵ = 0.12 mm1
c = 3.7035 (12) ÅT = 293 K
V = 1688.3 (9) Å3Prism, orange
Z = 40.32 × 0.10 × 0.06 mm
Data collection top
Bruker APEX-II CCD area-detector
diffractometer
1501 independent reflections
Radiation source: fine-focus sealed tube937 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.080
φ and ω scansθmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1616
Tmin = 0.764, Tmax = 1.000k = 3933
8125 measured reflectionsl = 44
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.098 w = 1/[σ2(Fo2) + (0.0266P)2 + 0.8222P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
1501 reflectionsΔρmax = 0.19 e Å3
139 parametersΔρmin = 0.21 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0066 (9)
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
O10.67031 (11)0.18837 (5)0.0947 (5)0.0419 (5)
O20.80743 (12)0.15239 (5)0.1262 (5)0.0478 (6)
N10.52753 (13)0.05362 (6)0.7689 (5)0.0298 (5)
N20.59041 (14)0.12359 (5)0.4411 (6)0.0318 (5)
N30.78629 (13)0.03824 (6)0.8291 (5)0.0300 (5)
N40.84166 (13)0.00537 (5)0.9557 (6)0.0304 (5)
C10.76584 (17)0.18283 (7)0.0452 (7)0.0305 (6)
C20.81729 (16)0.21767 (6)0.1117 (7)0.0263 (6)
C30.91983 (17)0.21782 (7)0.1133 (7)0.0319 (6)
C40.9707 (3)0.25000.25000.0352 (9)
C50.7663 (2)0.25000.25000.0279 (8)
C60.65412 (17)0.09647 (7)0.5559 (7)0.0299 (6)
C70.49508 (17)0.11594 (7)0.4963 (7)0.0325 (6)
C80.46423 (17)0.08147 (7)0.6597 (7)0.0324 (6)
C90.62337 (16)0.06146 (7)0.7166 (6)0.0245 (6)
C100.69375 (16)0.03105 (7)0.8372 (6)0.0243 (6)
H10.64580.16820.17970.063*
H4A0.90660.00880.90680.036*
H30.95430.19620.02180.038*
H41.03930.25000.25000.042*
H50.69760.25000.25000.034*
H60.72140.10110.52770.036*
H70.44820.13440.42230.039*
H80.39700.07740.69530.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0312 (10)0.0309 (11)0.0637 (14)0.0015 (8)0.0054 (9)0.0152 (10)
O20.0411 (11)0.0298 (11)0.0724 (15)0.0076 (9)0.0023 (10)0.0182 (10)
N10.0258 (10)0.0272 (11)0.0365 (13)0.0000 (10)0.0014 (10)0.0022 (10)
N20.0319 (12)0.0230 (11)0.0406 (14)0.0031 (10)0.0038 (10)0.0040 (10)
N30.0244 (10)0.0216 (11)0.0440 (14)0.0034 (9)0.0009 (9)0.0019 (10)
N40.0218 (10)0.0228 (11)0.0466 (13)0.0019 (9)0.0063 (9)0.0060 (10)
C10.0318 (14)0.0283 (14)0.0314 (15)0.0005 (12)0.0028 (12)0.0002 (12)
C20.0316 (13)0.0223 (13)0.0249 (14)0.0010 (10)0.0012 (11)0.0005 (11)
C30.0331 (14)0.0293 (15)0.0334 (16)0.0046 (12)0.0020 (12)0.0005 (12)
C40.0289 (18)0.033 (2)0.043 (2)0.0000.0000.0004 (18)
C50.0268 (17)0.0293 (19)0.028 (2)0.0000.0000.0020 (16)
C60.0268 (13)0.0243 (13)0.0385 (16)0.0002 (11)0.0035 (11)0.0012 (12)
C70.0305 (14)0.0295 (14)0.0375 (15)0.0068 (12)0.0013 (11)0.0045 (13)
C80.0253 (12)0.0307 (14)0.0411 (16)0.0039 (12)0.0009 (12)0.0054 (13)
C90.0251 (12)0.0210 (13)0.0272 (14)0.0011 (10)0.0013 (11)0.0023 (10)
C100.0255 (12)0.0214 (13)0.0259 (14)0.0004 (11)0.0027 (10)0.0017 (11)
Geometric parameters (Å, º) top
O1—C11.320 (3)C2—C51.387 (3)
O1—H10.8200C2—C31.389 (3)
O2—C11.207 (3)C3—C41.380 (3)
N1—C81.333 (3)C3—H30.9300
N1—C91.339 (3)C4—H40.9300
N2—C61.326 (3)C5—H50.9300
N2—C71.333 (3)C6—C91.384 (3)
N3—C101.277 (3)C6—H60.9300
N3—N41.416 (2)C7—C81.373 (3)
N4—C10i1.388 (3)C7—H70.9300
N4—H4A0.9052C8—H80.9300
C1—C21.483 (3)C9—C101.468 (3)
C1—O1—H1109.5C2ii—C5—C2120.2 (3)
C8—N1—C9116.2 (2)C2ii—C5—H5119.9
C6—N2—C7116.6 (2)C2—C5—H5119.9
C10—N3—N4111.35 (19)N2—C6—C9121.9 (2)
C10i—N4—N3113.73 (16)N2—C6—H6119.1
C10i—N4—H4A112.7C9—C6—H6119.1
N3—N4—H4A110.4N2—C7—C8121.7 (2)
O2—C1—O1122.9 (2)N2—C7—H7119.1
O2—C1—C2123.3 (2)C8—C7—H7119.1
O1—C1—C2113.8 (2)N1—C8—C7122.1 (2)
C5—C2—C3119.6 (2)N1—C8—H8118.9
C5—C2—C1122.1 (2)C7—C8—H8118.9
C3—C2—C1118.3 (2)N1—C9—C6121.5 (2)
C4—C3—C2120.2 (2)N1—C9—C10116.6 (2)
C4—C3—H3119.9C6—C9—C10121.9 (2)
C2—C3—H3119.9N3—C10—N4i120.9 (2)
C3ii—C4—C3120.1 (3)N3—C10—C9119.9 (2)
C3ii—C4—H4120.0N4i—C10—C9119.18 (18)
C3—C4—H4120.0
C10—N3—N4—C10i40.8 (2)C9—N1—C8—C71.2 (4)
O2—C1—C2—C5170.5 (2)N2—C7—C8—N10.7 (4)
O1—C1—C2—C510.6 (3)C8—N1—C9—C60.4 (3)
O2—C1—C2—C310.5 (4)C8—N1—C9—C10179.8 (2)
O1—C1—C2—C3168.3 (2)N2—C6—C9—N11.1 (4)
C5—C2—C3—C40.3 (3)N2—C6—C9—C10178.7 (2)
C1—C2—C3—C4178.68 (18)N4—N3—C10—N4i0.6 (3)
C2—C3—C4—C3ii0.15 (17)N4—N3—C10—C9179.99 (19)
C3—C2—C5—C2ii0.15 (17)N1—C9—C10—N3173.0 (2)
C1—C2—C5—C2ii178.8 (3)C6—C9—C10—N37.2 (4)
C7—N2—C6—C91.7 (4)N1—C9—C10—N4i7.6 (3)
C6—N2—C7—C80.8 (4)C6—C9—C10—N4i172.2 (2)
Symmetry codes: (i) x+3/2, y, z; (ii) x, y+1/2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N20.821.942.751 (3)173
C6—H6···O20.932.563.223 (3)129
N4—H4A···N1iii0.912.533.165 (3)128
N4—H4A···N1i0.912.342.749 (3)107
Symmetry codes: (i) x+3/2, y, z; (iii) x+1/2, y, z+2.
 

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