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The 1:1 adduct of 1,4-di­aza­bi­cyclo­[2.2.2]­octane and 5-hydroxy­isophthalic acid is a salt, [H(C6H12N2)]+·­[HOC6H3(COOH)COO] or C6H13N2+·C8H5O5. The ions are linked by three types of hydrogen bond, i.e. N—H...O, O—H...O and O—H...N, into continuous two-dimensional (4,4) nets built from a single type of R{_{10}^{10}}(58) ring. Six independent sheets of this type make up the structure and these are interwoven in sets of three.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010000771X/gg1007sup1.cif
Contains datablocks global, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010000771X/gg1007IIIsup2.hkl
Contains datablock III

CCDC reference: 150845

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2000); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

1,4-Diazabicyclo[2.2.2]octane–5-hydroxyisophthalic acid (1/1) top
Crystal data top
C6H13N2+·C8H5O5F(000) = 1248
Mr = 294.30Dx = 1.403 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 17.3820 (7) ÅCell parameters from 3119 reflections
b = 6.7257 (3) Åθ = 2.8–27.5°
c = 23.9374 (9) ŵ = 0.11 mm1
β = 95.368 (2)°T = 100 K
V = 2786.2 (2) Å3Block, colourless
Z = 80.25 × 0.25 × 0.23 mm
Data collection top
KappaCCD
diffractometer
3119 independent reflections
Radiation source: fine-focus sealed X-ray tube2441 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
φ scans and ω scans with κ offsetsθmax = 27.5°, θmin = 2.8°
Absorption correction: multi scan
(DENZO-SMN; Otwinowski & Minor, 1997)
h = 022
Tmin = 0.974, Tmax = 0.976k = 08
3374 measured reflectionsl = 2930
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)] = 0.046H-atom parameters constrained
wR(F2) = 0.121 w = 1/[σ2(Fo2) + (0.0468P)2 + 2.4139P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
3119 reflectionsΔρmax = 0.30 e Å3
193 parametersΔρmin = 0.32 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0025 (7)
Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G. C. & Holmes, K. C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program, hence the `multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the `size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.39457 (9)0.05729 (19)0.26981 (5)0.0418 (4)
O20.40922 (7)0.23375 (17)0.22730 (4)0.0275 (3)
O30.40066 (7)0.25995 (19)0.01873 (5)0.0324 (3)
O40.32665 (8)0.03613 (19)0.02918 (5)0.0362 (3)
O50.28335 (7)0.49964 (17)0.11376 (5)0.0282 (3)
C110.37110 (8)0.0418 (2)0.17004 (6)0.0191 (3)
C120.37641 (8)0.0701 (2)0.12141 (6)0.0191 (3)
C130.35333 (8)0.0129 (2)0.06887 (6)0.0188 (3)
C140.32246 (8)0.2052 (2)0.06578 (6)0.0197 (3)
C150.31530 (8)0.3148 (2)0.11451 (6)0.0198 (3)
C160.34178 (8)0.2345 (2)0.16651 (6)0.0202 (3)
C170.39303 (9)0.0436 (2)0.22738 (6)0.0218 (3)
C180.35997 (9)0.1036 (2)0.01545 (6)0.0229 (4)
N10.41700 (7)0.39877 (19)0.32670 (5)0.0208 (3)
N20.40638 (7)0.5779 (2)0.41892 (5)0.0210 (3)
C10.34314 (9)0.5094 (3)0.32486 (7)0.0245 (4)
C20.48131 (9)0.5425 (2)0.33731 (7)0.0234 (4)
C30.41909 (10)0.2537 (2)0.37345 (7)0.0241 (4)
C40.33853 (10)0.6288 (3)0.37880 (7)0.0343 (4)
C50.47902 (11)0.6391 (3)0.39542 (8)0.0412 (5)
C60.40781 (13)0.3597 (3)0.42890 (7)0.0366 (5)
H20.41370.27650.26040.041*
H50.25650.51730.08310.042*
H120.39560.20240.12400.023*
H140.30620.26150.03020.024*
H160.33980.31160.19960.024*
H2A0.40240.64380.45270.025*
H1A0.33900.60060.29230.029*
H1B0.29940.41460.32010.029*
H2B0.53120.47300.33550.028*
H2C0.47700.64670.30800.028*
H3A0.37770.15370.36540.029*
H3B0.46940.18340.37680.029*
H4A0.29010.59650.39550.041*
H4B0.33860.77290.37040.041*
H5A0.48080.78570.39200.049*
H5B0.52430.59570.42070.049*
H6A0.45060.32540.45750.044*
H6B0.35870.31660.44290.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0797 (10)0.0264 (7)0.0181 (6)0.0110 (7)0.0025 (6)0.0019 (5)
O20.0444 (7)0.0218 (6)0.0163 (6)0.0078 (5)0.0026 (5)0.0030 (5)
O30.0471 (7)0.0300 (7)0.0200 (6)0.0158 (6)0.0016 (5)0.0029 (5)
O40.0536 (8)0.0328 (7)0.0200 (6)0.0125 (6)0.0087 (5)0.0037 (5)
O50.0394 (7)0.0198 (6)0.0241 (6)0.0083 (5)0.0033 (5)0.0016 (5)
C110.0181 (7)0.0217 (8)0.0172 (8)0.0006 (6)0.0008 (6)0.0017 (6)
C120.0187 (7)0.0187 (7)0.0201 (8)0.0019 (6)0.0020 (6)0.0011 (6)
C130.0178 (7)0.0209 (8)0.0180 (8)0.0002 (6)0.0023 (6)0.0004 (6)
C140.0201 (7)0.0210 (8)0.0174 (8)0.0003 (6)0.0006 (6)0.0032 (6)
C150.0207 (7)0.0166 (7)0.0220 (8)0.0011 (6)0.0011 (6)0.0000 (6)
C160.0225 (7)0.0199 (8)0.0180 (8)0.0007 (6)0.0018 (6)0.0021 (6)
C170.0267 (8)0.0214 (8)0.0174 (8)0.0022 (7)0.0019 (6)0.0005 (6)
C180.0278 (8)0.0225 (8)0.0181 (8)0.0021 (7)0.0010 (6)0.0009 (6)
N10.0240 (6)0.0179 (7)0.0207 (7)0.0021 (5)0.0036 (5)0.0021 (5)
N20.0249 (6)0.0205 (7)0.0179 (7)0.0018 (5)0.0034 (5)0.0037 (5)
C10.0235 (8)0.0276 (9)0.0219 (8)0.0004 (7)0.0009 (6)0.0001 (7)
C20.0235 (7)0.0230 (8)0.0244 (9)0.0033 (7)0.0061 (6)0.0025 (7)
C30.0325 (8)0.0170 (8)0.0232 (8)0.0005 (7)0.0044 (7)0.0002 (6)
C40.0304 (9)0.0463 (12)0.0256 (9)0.0147 (9)0.0001 (7)0.0040 (8)
C50.0360 (10)0.0475 (12)0.0427 (12)0.0205 (9)0.0172 (8)0.0245 (10)
C60.0644 (13)0.0220 (9)0.0229 (9)0.0040 (9)0.0006 (8)0.0016 (7)
Geometric parameters (Å, º) top
O1—C171.220 (2)N1—C31.483 (2)
O2—C171.310 (2)N2—C61.487 (2)
O2—H20.84N2—C51.487 (2)
O3—C181.2654 (19)N2—C41.489 (2)
O4—C181.2518 (19)N2—H2A0.93
O5—C151.3609 (18)C1—C41.529 (2)
O5—H50.84C1—H1A0.99
C11—C161.393 (2)C1—H1B0.99
C11—C121.397 (2)C2—C51.539 (2)
C11—C171.504 (2)C2—H2B0.99
C12—C131.400 (2)C2—H2C0.99
C12—H120.95C3—C61.535 (2)
C13—C141.399 (2)C3—H3A0.99
C13—C181.513 (2)C3—H3B0.99
C14—C151.396 (2)C4—H4A0.99
C14—H140.95C4—H4B0.99
C15—C161.395 (2)C5—H5A0.99
C16—H160.95C5—H5B0.99
N1—C11.481 (2)C6—H6A0.99
N1—C21.482 (2)C6—H6B0.99
C17—O2—H2109.5N1—C1—H1A109.5
C15—O5—H5109.5C4—C1—H1A109.5
C16—C11—C12120.23 (14)N1—C1—H1B109.5
C16—C11—C17118.10 (14)C4—C1—H1B109.5
C12—C11—C17121.61 (14)H1A—C1—H1B108.1
C11—C12—C13119.86 (14)N1—C2—C5110.33 (12)
C11—C12—H12120.1N1—C2—H2B109.6
C13—C12—H12120.1C5—C2—H2B109.6
C14—C13—C12119.50 (14)N1—C2—H2C109.6
C14—C13—C18119.56 (13)C5—C2—H2C109.6
C12—C13—C18120.94 (14)H2B—C2—H2C108.1
C15—C14—C13120.53 (14)N1—C3—C6110.54 (13)
C15—C14—H14119.7N1—C3—H3A109.5
C13—C14—H14119.7C6—C3—H3A109.5
O5—C15—C14122.67 (14)N1—C3—H3B109.5
C16—C15—C14119.58 (14)C6—C3—H3B109.5
C11—C16—C15120.20 (14)H3A—C3—H3B108.1
C11—C16—H16119.9N2—C4—C1108.85 (13)
C15—C16—H16119.9N2—C4—H4A109.9
O1—C17—O2123.82 (15)C1—C4—H4A109.9
O1—C17—C11122.12 (15)N2—C4—H4B109.9
O2—C17—C11114.06 (13)C1—C4—H4B109.9
O5—C15—C16117.75 (14)H4A—C4—H4B108.3
O3—C18—O4124.45 (15)N2—C5—C2108.65 (13)
O3—C18—C13117.66 (13)N2—C5—H5A110.0
O4—C18—C13117.86 (14)C2—C5—H5A110.0
C1—N1—C2108.39 (12)N2—C5—H5B110.0
C1—N1—C3108.23 (12)C2—C5—H5B110.0
C2—N1—C3109.58 (12)H5A—C5—H5B108.3
C6—N2—C5109.36 (15)N2—C6—C3108.73 (14)
C6—N2—C4109.30 (14)N2—C6—H6A109.9
C5—N2—C4109.98 (14)C3—C6—H6A109.9
C6—N2—H2A109.4N2—C6—H6B109.9
C5—N2—H2A109.4C3—C6—H6B109.9
C4—N2—H2A109.4H6A—C6—H6B108.3
N1—C1—C4110.65 (13)
C16—C11—C12—C131.0 (2)C12—C13—C18—O4168.04 (15)
C17—C11—C12—C13178.17 (13)C14—C13—C18—O3167.21 (14)
C11—C12—C13—C142.3 (2)C2—N1—C1—C455.71 (17)
C11—C12—C13—C18178.77 (13)C3—N1—C1—C463.07 (17)
C12—C13—C14—C150.6 (2)C1—N1—C2—C563.97 (18)
C18—C13—C14—C15179.56 (13)C3—N1—C2—C553.95 (18)
C13—C14—C15—O5177.80 (14)C1—N1—C3—C655.96 (17)
C13—C14—C15—C162.4 (2)C2—N1—C3—C662.05 (17)
C12—C11—C16—C152.0 (2)C6—N2—C4—C156.65 (18)
C17—C11—C16—C15175.25 (14)C5—N2—C4—C163.42 (19)
O5—C15—C16—C11176.47 (13)N1—C1—C4—N26.2 (2)
C14—C15—C16—C113.7 (2)C6—N2—C5—C264.92 (19)
C16—C11—C17—O18.8 (2)C4—N2—C5—C255.1 (2)
C12—C11—C17—O1173.96 (15)N1—C2—C5—N27.9 (2)
C16—C11—C17—O2170.51 (13)C5—N2—C6—C357.00 (19)
C12—C11—C17—O26.7 (2)C4—N2—C6—C363.44 (18)
C14—C13—C18—O410.9 (2)N1—C3—C6—N25.7 (2)
C12—C13—C18—O313.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N10.841.782.6175 (17)172
O5—H5···O4i0.841.852.6628 (17)162
N2—H2A···O3ii0.931.712.6365 (17)173
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x, y1, z+1/2.
 

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