Threefold interweaving of (4,4) nets built from R(58) rings in the hydrogen-bonded adduct 1,4-diaza­bicyclo[2.2.2]octane–5-hydroxy­isophthalic acid (1/1)

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(58) ring. Six independent sheets of this type make up the structure and these are interwoven in sets of three.

Computing details

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)

Crystal data

C6H13N2^+·C8H5O5^−	F(000) = 1248
Mr = 294.30	Dx = 1.403 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.3820 (7) Å	Cell parameters from 3119 reflections
b = 6.7257 (3) Å	θ = 2.8–27.5°
c = 23.9374 (9) Å	µ = 0.11 mm^−1
β = 95.368 (2)°	T = 100 K
V = 2786.2 (2) Å^3	Block, colourless
Z = 8	0.25 × 0.25 × 0.23 mm

Data collection

KappaCCD diffractometer	3119 independent reflections
Radiation source: fine-focus sealed X-ray tube	2441 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ scans and ω scans with κ offsets	θmax = 27.5°, θmin = 2.8°
Absorption correction: multi scan (DENZO-SMN; Otwinowski & Minor, 1997)	h = 0→22
Tmin = 0.974, Tmax = 0.976	k = 0→8
3374 measured reflections	l = −29→30

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.121	w = 1/[σ^2(Fo^2) + (0.0468P)^2 + 2.4139P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
3119 reflections	Δρmax = 0.30 e Å^−3
193 parameters	Δρmin = −0.32 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0025 (7)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.39457 (9)	0.05729 (19)	0.26981 (5)	0.0418 (4)
O2	0.40922 (7)	−0.23375 (17)	0.22730 (4)	0.0275 (3)
O3	0.40066 (7)	−0.25995 (19)	0.01873 (5)	0.0324 (3)
O4	0.32665 (8)	−0.03613 (19)	−0.02918 (5)	0.0362 (3)
O5	0.28335 (7)	0.49964 (17)	0.11376 (5)	0.0282 (3)
C11	0.37110 (8)	0.0418 (2)	0.17004 (6)	0.0191 (3)
C12	0.37641 (8)	−0.0701 (2)	0.12141 (6)	0.0191 (3)
C13	0.35333 (8)	0.0129 (2)	0.06887 (6)	0.0188 (3)
C14	0.32246 (8)	0.2052 (2)	0.06578 (6)	0.0197 (3)
C15	0.31530 (8)	0.3148 (2)	0.11451 (6)	0.0198 (3)
C16	0.34178 (8)	0.2345 (2)	0.16651 (6)	0.0202 (3)
C17	0.39303 (9)	−0.0436 (2)	0.22738 (6)	0.0218 (3)
C18	0.35997 (9)	−0.1036 (2)	0.01545 (6)	0.0229 (4)
N1	0.41700 (7)	−0.39877 (19)	0.32670 (5)	0.0208 (3)
N2	0.40638 (7)	−0.5779 (2)	0.41892 (5)	0.0210 (3)
C1	0.34314 (9)	−0.5094 (3)	0.32486 (7)	0.0245 (4)
C2	0.48131 (9)	−0.5425 (2)	0.33731 (7)	0.0234 (4)
C3	0.41909 (10)	−0.2537 (2)	0.37345 (7)	0.0241 (4)
C4	0.33853 (10)	−0.6288 (3)	0.37880 (7)	0.0343 (4)
C5	0.47902 (11)	−0.6391 (3)	0.39542 (8)	0.0412 (5)
C6	0.40781 (13)	−0.3597 (3)	0.42890 (7)	0.0366 (5)
H2	0.4137	−0.2765	0.2604	0.041*
H5	0.2565	0.5173	0.0831	0.042*
H12	0.3956	−0.2024	0.1240	0.023*
H14	0.3062	0.2615	0.0302	0.024*
H16	0.3398	0.3116	0.1996	0.024*
H2A	0.4024	−0.6438	0.4527	0.025*
H1A	0.3390	−0.6006	0.2923	0.029*
H1B	0.2994	−0.4146	0.3201	0.029*
H2B	0.5312	−0.4730	0.3355	0.028*
H2C	0.4770	−0.6467	0.3080	0.028*
H3A	0.3777	−0.1537	0.3654	0.029*
H3B	0.4694	−0.1834	0.3768	0.029*
H4A	0.2901	−0.5965	0.3955	0.041*
H4B	0.3386	−0.7729	0.3704	0.041*
H5A	0.4808	−0.7857	0.3920	0.049*
H5B	0.5243	−0.5957	0.4207	0.049*
H6A	0.4506	−0.3254	0.4575	0.044*
H6B	0.3587	−0.3166	0.4429	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0797 (10)	0.0264 (7)	0.0181 (6)	0.0110 (7)	−0.0025 (6)	−0.0019 (5)
O2	0.0444 (7)	0.0218 (6)	0.0163 (6)	0.0078 (5)	0.0026 (5)	0.0030 (5)
O3	0.0471 (7)	0.0300 (7)	0.0200 (6)	0.0158 (6)	0.0016 (5)	−0.0029 (5)
O4	0.0536 (8)	0.0328 (7)	0.0200 (6)	0.0125 (6)	−0.0087 (5)	−0.0037 (5)
O5	0.0394 (7)	0.0198 (6)	0.0241 (6)	0.0083 (5)	−0.0033 (5)	−0.0016 (5)
C11	0.0181 (7)	0.0217 (8)	0.0172 (8)	−0.0006 (6)	0.0008 (6)	0.0017 (6)
C12	0.0187 (7)	0.0187 (7)	0.0201 (8)	0.0019 (6)	0.0020 (6)	0.0011 (6)
C13	0.0178 (7)	0.0209 (8)	0.0180 (8)	0.0002 (6)	0.0023 (6)	−0.0004 (6)
C14	0.0201 (7)	0.0210 (8)	0.0174 (8)	−0.0003 (6)	−0.0006 (6)	0.0032 (6)
C15	0.0207 (7)	0.0166 (7)	0.0220 (8)	0.0011 (6)	0.0011 (6)	0.0000 (6)
C16	0.0225 (7)	0.0199 (8)	0.0180 (8)	−0.0007 (6)	0.0018 (6)	−0.0021 (6)
C17	0.0267 (8)	0.0214 (8)	0.0174 (8)	0.0022 (7)	0.0019 (6)	0.0005 (6)
C18	0.0278 (8)	0.0225 (8)	0.0181 (8)	0.0021 (7)	0.0010 (6)	−0.0009 (6)
N1	0.0240 (6)	0.0179 (7)	0.0207 (7)	0.0021 (5)	0.0036 (5)	0.0021 (5)
N2	0.0249 (6)	0.0205 (7)	0.0179 (7)	−0.0018 (5)	0.0034 (5)	0.0037 (5)
C1	0.0235 (8)	0.0276 (9)	0.0219 (8)	0.0004 (7)	−0.0009 (6)	0.0001 (7)
C2	0.0235 (7)	0.0230 (8)	0.0244 (9)	0.0033 (7)	0.0061 (6)	0.0025 (7)
C3	0.0325 (8)	0.0170 (8)	0.0232 (8)	0.0005 (7)	0.0044 (7)	−0.0002 (6)
C4	0.0304 (9)	0.0463 (12)	0.0256 (9)	−0.0147 (9)	−0.0001 (7)	0.0040 (8)
C5	0.0360 (10)	0.0475 (12)	0.0427 (12)	0.0205 (9)	0.0172 (8)	0.0245 (10)
C6	0.0644 (13)	0.0220 (9)	0.0229 (9)	−0.0040 (9)	0.0006 (8)	−0.0016 (7)

Geometric parameters (Å, º)

O1—C17	1.220 (2)	N1—C3	1.483 (2)
O2—C17	1.310 (2)	N2—C6	1.487 (2)
O2—H2	0.84	N2—C5	1.487 (2)
O3—C18	1.2654 (19)	N2—C4	1.489 (2)
O4—C18	1.2518 (19)	N2—H2A	0.93
O5—C15	1.3609 (18)	C1—C4	1.529 (2)
O5—H5	0.84	C1—H1A	0.99
C11—C16	1.393 (2)	C1—H1B	0.99
C11—C12	1.397 (2)	C2—C5	1.539 (2)
C11—C17	1.504 (2)	C2—H2B	0.99
C12—C13	1.400 (2)	C2—H2C	0.99
C12—H12	0.95	C3—C6	1.535 (2)
C13—C14	1.399 (2)	C3—H3A	0.99
C13—C18	1.513 (2)	C3—H3B	0.99
C14—C15	1.396 (2)	C4—H4A	0.99
C14—H14	0.95	C4—H4B	0.99
C15—C16	1.395 (2)	C5—H5A	0.99
C16—H16	0.95	C5—H5B	0.99
N1—C1	1.481 (2)	C6—H6A	0.99
N1—C2	1.482 (2)	C6—H6B	0.99
C17—O2—H2	109.5	N1—C1—H1A	109.5
C15—O5—H5	109.5	C4—C1—H1A	109.5
C16—C11—C12	120.23 (14)	N1—C1—H1B	109.5
C16—C11—C17	118.10 (14)	C4—C1—H1B	109.5
C12—C11—C17	121.61 (14)	H1A—C1—H1B	108.1
C11—C12—C13	119.86 (14)	N1—C2—C5	110.33 (12)
C11—C12—H12	120.1	N1—C2—H2B	109.6
C13—C12—H12	120.1	C5—C2—H2B	109.6
C14—C13—C12	119.50 (14)	N1—C2—H2C	109.6
C14—C13—C18	119.56 (13)	C5—C2—H2C	109.6
C12—C13—C18	120.94 (14)	H2B—C2—H2C	108.1
C15—C14—C13	120.53 (14)	N1—C3—C6	110.54 (13)
C15—C14—H14	119.7	N1—C3—H3A	109.5
C13—C14—H14	119.7	C6—C3—H3A	109.5
O5—C15—C14	122.67 (14)	N1—C3—H3B	109.5
C16—C15—C14	119.58 (14)	C6—C3—H3B	109.5
C11—C16—C15	120.20 (14)	H3A—C3—H3B	108.1
C11—C16—H16	119.9	N2—C4—C1	108.85 (13)
C15—C16—H16	119.9	N2—C4—H4A	109.9
O1—C17—O2	123.82 (15)	C1—C4—H4A	109.9
O1—C17—C11	122.12 (15)	N2—C4—H4B	109.9
O2—C17—C11	114.06 (13)	C1—C4—H4B	109.9
O5—C15—C16	117.75 (14)	H4A—C4—H4B	108.3
O3—C18—O4	124.45 (15)	N2—C5—C2	108.65 (13)
O3—C18—C13	117.66 (13)	N2—C5—H5A	110.0
O4—C18—C13	117.86 (14)	C2—C5—H5A	110.0
C1—N1—C2	108.39 (12)	N2—C5—H5B	110.0
C1—N1—C3	108.23 (12)	C2—C5—H5B	110.0
C2—N1—C3	109.58 (12)	H5A—C5—H5B	108.3
C6—N2—C5	109.36 (15)	N2—C6—C3	108.73 (14)
C6—N2—C4	109.30 (14)	N2—C6—H6A	109.9
C5—N2—C4	109.98 (14)	C3—C6—H6A	109.9
C6—N2—H2A	109.4	N2—C6—H6B	109.9
C5—N2—H2A	109.4	C3—C6—H6B	109.9
C4—N2—H2A	109.4	H6A—C6—H6B	108.3
N1—C1—C4	110.65 (13)
C16—C11—C12—C13	1.0 (2)	C12—C13—C18—O4	168.04 (15)
C17—C11—C12—C13	178.17 (13)	C14—C13—C18—O3	167.21 (14)
C11—C12—C13—C14	−2.3 (2)	C2—N1—C1—C4	55.71 (17)
C11—C12—C13—C18	178.77 (13)	C3—N1—C1—C4	−63.07 (17)
C12—C13—C14—C15	0.6 (2)	C1—N1—C2—C5	−63.97 (18)
C18—C13—C14—C15	179.56 (13)	C3—N1—C2—C5	53.95 (18)
C13—C14—C15—O5	−177.80 (14)	C1—N1—C3—C6	55.96 (17)
C13—C14—C15—C16	2.4 (2)	C2—N1—C3—C6	−62.05 (17)
C12—C11—C16—C15	2.0 (2)	C6—N2—C4—C1	56.65 (18)
C17—C11—C16—C15	−175.25 (14)	C5—N2—C4—C1	−63.42 (19)
O5—C15—C16—C11	176.47 (13)	N1—C1—C4—N2	6.2 (2)
C14—C15—C16—C11	−3.7 (2)	C6—N2—C5—C2	−64.92 (19)
C16—C11—C17—O1	−8.8 (2)	C4—N2—C5—C2	55.1 (2)
C12—C11—C17—O1	173.96 (15)	N1—C2—C5—N2	7.9 (2)
C16—C11—C17—O2	170.51 (13)	C5—N2—C6—C3	57.00 (19)
C12—C11—C17—O2	−6.7 (2)	C4—N2—C6—C3	−63.44 (18)
C14—C13—C18—O4	−10.9 (2)	N1—C3—C6—N2	5.7 (2)
C12—C13—C18—O3	−13.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.84	1.78	2.6175 (17)	172
O5—H5···O4^i	0.84	1.85	2.6628 (17)	162
N2—H2A···O3^ii	0.93	1.71	2.6365 (17)	173

Symmetry codes: (i) −x+1/2, −y+1/2, −z; (ii) x, −y−1, z+1/2.