Proton-transfer and non-transfer in compounds of quinoline and quinaldic acid with L-tartaric acid

The structures of two compounds of L-tartaric acid with quinoline, viz. the proton-transfer compound quinolinium hydrogen (2R,3R)-tartrate monohydrate, C₉H₈N⁺·C₄H₅O₆^-·H₂O, (I), and the anhydrous non-proton-transfer adduct with quinaldic acid, bis­(quinolinium-2-carboxyl­ate) (2R,3R)-tar­taric acid, 2C₁₀H₇NO₂·C₄H₆O₆, (II), have been determined at 130 K. Compound (I) has a three-dimensional honeycomb substructure formed from head-to-tail hydrogen-bonded hydrogen tartrate anions and water mol­ecules. The stacks of [pi]-bonded quinolinium cations are accommodated within the channels and are hydrogen bonded to it peripherally. Compound (II) has a two-dimensional network structure based on pseudo-centrosymmetric head-to-tail hydrogen-bonded cyclic dimers comprising zwitterionic quinaldic acid species which are inter­linked by tartaric acid mol­ecules.

S1. Comment

Tartaric acid represents a relatively strong diprotic chiral α-hydroxy acid (pK_a1, 2.93; pK_a2, 4.23) and therefore is potentially capable of forming both 1:1 and 1:2 proton-transfer salts with most Lewis bases. However, with stoichiometric control, it is possible to selectively form 1:1 hydrogen tartrates and the crystal structures of a large number of these 1:1 salts have been reported, particularly since these compounds usually have good crystal morphology, allowing structure determination by single-crystal X-ray analysis which is often not possible with the parent Lewis base. Applications have been with drugs such as epinephrine (Carlström, 1973), dextromoramide (Bye, 1975), amosulalol (Furuya et al., 1989), alprenolol (Główka & Codding, 1989), phendimetrazine (Glaser et al., 1994) and tolterodine (Košutić-Hulita & Žegarac, 2005), as well as natural products such as alkaloids, e.g. strychnine (Gould et al., 1987), brucine (Smith, Wermuth & White, 2006), quinine (Ryttersgaard & Larsen, 2004), cinchonine (Puliti et al., 2001), cinchonidine (Ryttersgaard & Larsen, 2003; Zhang et al., 2003) and quincoridine (Kania et al., 2004), and amino acids e.g. L-alanine (Rajagopal et al., 2002), L-proline (Subha Nandhini et al., 2001), D–, L– and DL-histidine (Marchewska et al., 2003; Rajagopal et al., 2003; Johnson & Feeder, 2004a,b,c) and L-lysine (Debrus et al., 2005).

Because of the ready availability of L-(+)-tartaric acid which has the confirmed (2R,3R) absolute configuration, it has been very useful for both resolution and the crystallographic determination of absolute configuration in chiral molecular species e.g. with the anticholinergic agent R-(-)-1,1-diphenyl-3- piperidinobutan-1-ol (Schjelderup et al., 1990). More recently, its utility as an agent for the introduction of chirality in achiral organic compounds for the generation of crystalline materials with potentially useful nonlinear optical properties has been explored (Aakeröy et al., 1992; Fuller et al., 1995; Marchewska et al., 2003; Debrus et al., 2005; Manivannan et al., 2006 or ?? 2005).

We have found that 1:1 stoichiometric interactions of the relatively strong carboxylic acids 5-sulfosalicylic acid (5-SSA) (Smith et al., 2004) and 3,5-dinitrosalicylic acid (DNSA) (Smith, Wermuth, Healy & White, 2006) with a series of bicyclic heteroaromatic amines including quinoline, tetrahydroquinoline, 8-hydroxyquinoline, 8-aminoquinoline and quinaldic acid (quinoline-2-carboxylic acid, QA) mostly gave 1:1 proton-transfer compounds. The only exception was with quinaldic acid and 5-SSA, where an adduct salt compound [QA⁺.5-SSA⁻·QA] was found. In this structure, a unusual head-to-tail hydrogen-bonded cyclic homodimer was present [graph set R²₂(10); Etter, 1991] involving two QA species, one protonated, the other zwitterionic. With quinaldic acid itself, the crystal structure (Dobrzyńska & Jerzykiewicz, 2004) showed the presence of a tautomeric mixture of both zwitterionic and normal acid molecules with the zwitterions forming a similar homodimer. This was not the case with DNSA, where a conventional 1:1 product was formed with the QA molecule fully protonated.

The 1:1 reaction of these heteroaromatic amines with L-tartaric acid might be expected to give similar quinolinium hydrogen L-tartrates. Although the structures of the 1:1 tartrate salts of the previously mentioned quinine alkaloids are known (Puliti et al., 2001; Zhang et al., 2003; Ryttersgaard & Larsen, 2003, 2004; Kania et al., 2004), those with the simple analogues of quinoline are not common. The only other tartrates of simple polycyclic heteroaromatic amines are those with benzimidazole (proton-transfer) (Aakeröy & Hitchcock, 1994) and the non-transfer 1:1 adduct with 1,10-phenanthroline (Wang et al., 2006). Our 1:1 stoichiometric reaction of L-tartaric acid with quinoline (pK_a = 4.81) resulted in the isolation of the expected proton-transfer compound, a 1:1 hydrate, quinolinium hydrogen (2R,3R)-tartrate monohydrate, (I). However, with quinaldic acid, the adduct quinolinium-2-carboxylate–(2R,3R)-tartaric acid (2/1), (II), was formed. This compound differs from the 5-SSA–QA compound with the absence of proton transfer, the two QA molecules being zwitterionic. The structures of both (I) and (II) are reported here. With the other quinoline analogues 8-hydroxyquinoline and 8-aminoquinoline, the non-crystalline products obtained with L-tartaric acid did not allow a full series structural comparison to be made with the quinoline salts of DNSA and 5-SSA.

Compound (I) shows the presence of single proton transfer from L-tartaric acid to the hetero N atom of quinoline (Fig. 1). The hydrogen tartrate anions and the water molecules of solvation then form an unusual three-dimensional hydrogen-bonded honeycomb substructure through carboxylate interactions with other tartrate carboxylic acid and hydroxyl groups, as well as with the water molecule (Table 1). This structure extends down the a cell direction and accommodates the columns of π-stacked quinolinium cations within the channels (Figs. 2 and 3). The ring centroid separations for the alternating six-membered (N1/C2–C4/C10/C9 and C5–C10) ring systems of the quinolinium ions within the stacks are 3.7555 (11) and 3.7591 (11) Å, with an inter-ring dihedral angle of 4.22 (1)°. The cation stacks are peripherally hydrogen bonded to a carboxylate O-atom acceptor within the substructure through a single strong link [N⁺—H···O12, 2.6635 (18) Å]. Only two weak aromatic C—H···O interactions are present in the structure which in most respects is similar to that reported for the compound of L-tartaric acid with 1,10-phenanthroline (Wang et al., 2006).

With compound (II) (Fig. 4), surprisingly no proton transfer has occurred, the two QA species are zwitterionic, forming a pseudo-centrosymmetric head-to-tail hydrogen-bonded cyclic dimer similar to that found in the structure of the acid itself (Dobrzyńska & Jerzykiewicz, 2004). These R²₂(10) dimers are essentially planar [the torsion angles are N1—C2—C22—O22 = 5.4 (3)° and N1A—C2A—C22A—O22A = 4.1 (3)°], and are stabilized by both intermolecular and intramolecular N⁺—H···O interactions [N1···O22A = 2.747 (3) Å, N1A···O22 = 2.784 (3) Å, N1···O22 = 2.686 (3) Å and N1A···O22A = 2.668 (3) Å; Table 2], as well as longer aromatic C—H···O interactions [C8—H8···O22A = 3.181 (3) Å and C8A—H8A···O22 = 3.202 (3) Å]. This is also similar to the dimers found in the [QAH⁺.5-SSA⁻·QA] adduct, except that in this structure one of the QA species is fully protonated (Smith et al., 2004). It is therefore assumed that the absence of proton transfer in (II) is because of the stability of this zwitterionic dimer despite the pK_a difference for QA (pK_a1 = 4.96; pK_a2 = 9.02) versus tartaric acid. In (II), these dimers are linked through the tartaric acid molecules by head-to-tail heteromolecular carboxylic acid–carboxyl interactions (Table 2) which, together with homomolecular hydroxyl–carboxyl extensions, give a two-dimensional network structure (Fig. 5). Contrasting with the structure of (I) there are also numerous aromatic C—H···O associations with an absence of any π–π interactions between the QA molecules.

The accepted (2R,3R) absolute configuration for the L-tartrate residues in both (I) and (II) (Waser, 1949; Bijvoet et al., 1951; Hope & de la Camp, 1972) was assumed and in both compounds these adopt the common extended conformation which is similar to those of the parent tartaric acid (Stern & Beevers, 1950; Okaya et al., 1966; Albertsson et al., 1979), the L-acid in the anhydrous DL-acid (Luner et al., 2002) (Table 3) and in the 1:1 compound with 1,10-phenanthroline (Wang et al., 2006). However, unlike these, in both (I) and (II), a single hydroxyl–carboxyl intramolecular hydrogen bond is present [O—H···O = 2.6652 (17) and 2.639 (3) Å respectively].

While the absence of proton transfer in (II) may be explained in terms of the presence of the QA zwitterion dimer, the absence of transfer in the L-tartaric acid–1,10-phenanthroline compound reported by Wang et al. (2006) when compared with the structurally similar (I), is not understood, considering that the pK_a value for 1,10-phenanthroline (4.86) is very close to that of quinoline (4.81).

S2. Experimental

Both compounds were synthesized by heating 1 mmol quantities of L-tartaric acid and either quinoline [for (I)] or quinoline-2-carboxylic acid (quinaldic acid) [for (II)] in 50% 2-propanol–water for 10 min under reflux. Compound (I) was obtained as colourless needles (m.p. 397.6–398.6 K) and (II) as pale yellow plates (m.p. 469.1–470.7 K), after partial room-temperature evaporation of solvent.

S3. Refinement

H atoms potentially involved in hydrogen-bonding interactions in (I) and (II) were located by difference methods and their positional and isotropic displacement parameters were refined. However, with (II), because of the poor reflections/refined parameters ratio, the parameters were fixed for the final refinement cycle. Other H atoms for both (I) and (II) were included at calculated positions [C—H(aromatic) = 0.95 Å and C—H (aliphatic) = 0.97 or 0.98 Å] and treated as riding [U_iso(H) = 1.2U_eq(C)]. Friedel pairs were averaged for the data used in the refinements. The absolute configuration determined for the parent L-(+)-tartaric acid (2R,3R) (Waser, 1949; Bijvoet et al., 1951; Hope & de la Camp, 1972) was invoked in both structures.

Computing details

For both compounds, data collection: SMART (Bruker, 2000); cell refinement: SAINT ?? (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997) in WinGX (Farrugia, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) in WinGX; molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Figures

	Fig. 1. The molecular configuration and atom-numbering scheme for the quinolinium cation, the L-hydrogen tartrate anion and the water molecule of solvation in (I). Non-H atoms are shown as 50% probability displacement ellipsoids.
	Fig. 2. A view of the packing of (I) in the unit cell, viewed down the b axial direction, showing the columns of π-stacked quinolinium cations inside the tartrate–water honeycomb substructure. Hydrogen-bonding interactions are shown as broken lines and non-interactive H atoms have been omitted. [For symmetry codes, see Table 1.]
	Fig. 3. The packing of (I) in the unit cell, viewed approximately perpendicular to the honeycomb substructure. Hydrogen-bonding interactions are shown as broken lines and non-interactive H atoms have been omitted. [For symmetry codes, see Table 1.]
	Fig. 4. The molecular configuration and atom-numbering scheme for the two independent quinaldic acid zwitterions and the L-tartaric acid molecule in the asymmetric unit in (II). Non-H atoms are shown as 50% probability displacement ellipsoids.
	Fig. 5. A perspective view of the partial packing of (I) in the unit cell, showing the zwitterionic dimer units and their extension via the tartaric acid molecules. Hydrogen-bonding interactions are shown as broken lines and non-interactive H atoms have been omitted. [Symmetry code: (iv) x + 1, y + 1, z + 1. For other symmetry codes, see Table 2.]

(I) quinolinium hydrogen (2R),3R)-tartrate monohydrate

Crystal data

C9H8N^+·C4H5O6^−·H2O	Dx = 1.474 Mg m^−3
Mr = 297.26	Melting point = 397.6–398.6 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3131 reflections
a = 7.2546 (6) Å	θ = 2.2–27.3°
b = 9.4922 (8) Å	µ = 0.12 mm^−1
c = 19.4571 (16) Å	T = 130 K
V = 1339.86 (19) Å^3	Needle, colourless
Z = 4	0.50 × 0.20 × 0.20 mm
F(000) = 624

Data collection

Bruker SMART CCD area-detector diffractometer	1795 independent reflections
Radiation source: sealed tube	1668 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
ϕ and ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −8→9
Tmin = 0.88, Tmax = 1.00	k = −11→12
8431 measured reflections	l = −25→11

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)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.088	w = 1/[σ^2(Fo^2) + (0.0463P)^2 + 0.2433P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
1795 reflections	Δρmax = 0.25 e Å^−3
214 parameters	Δρmin = −0.19 e Å^−3
0 restraints	Absolute structure: Flack (1983), ? Friedel pairs?
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.2 (9)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.5299 (2)	0.39427 (15)	0.09300 (7)	0.0228 (4)
C2	0.5265 (2)	0.31413 (19)	0.14865 (8)	0.0272 (5)
C3	0.5210 (3)	0.16763 (19)	0.14294 (9)	0.0294 (5)
C4	0.5171 (3)	0.10805 (18)	0.07881 (9)	0.0288 (5)
C5	0.5157 (3)	0.13904 (18)	−0.04865 (9)	0.0288 (5)
C6	0.5179 (3)	0.2275 (2)	−0.10358 (9)	0.0303 (5)
C7	0.5274 (3)	0.37514 (19)	−0.09405 (9)	0.0290 (5)
C8	0.5315 (2)	0.43193 (17)	−0.02980 (9)	0.0256 (5)
C9	0.5274 (2)	0.34122 (16)	0.02752 (8)	0.0201 (4)
C10	0.5210 (2)	0.19313 (17)	0.01910 (8)	0.0220 (4)
O11	0.46959 (15)	0.82964 (11)	0.19086 (5)	0.0204 (3)
O12	0.46877 (15)	0.66946 (11)	0.10702 (5)	0.0206 (3)
O21	0.83201 (15)	0.68644 (13)	0.08832 (6)	0.0218 (3)
O31	0.76198 (17)	0.56444 (13)	0.22308 (6)	0.0262 (4)
O41	1.12483 (15)	0.81420 (12)	0.19773 (6)	0.0215 (3)
O42	1.12860 (16)	0.58184 (13)	0.22076 (7)	0.0304 (4)
C11	0.5477 (2)	0.75110 (15)	0.14794 (8)	0.0159 (4)
C21	0.7597 (2)	0.76063 (16)	0.14529 (8)	0.0170 (4)
C31	0.8378 (2)	0.69913 (17)	0.21149 (8)	0.0183 (4)
C41	1.0485 (2)	0.69145 (17)	0.20990 (7)	0.0178 (4)
O1W	0.17495 (18)	0.71359 (15)	0.02558 (6)	0.0281 (4)
H1	0.526 (3)	0.486 (2)	0.0993 (11)	0.036 (6)*
H2	0.52770	0.35670	0.19280	0.0330*
H3	0.52000	0.11010	0.18290	0.0350*
H4	0.51160	0.00850	0.07440	0.0350*
H5	0.51040	0.04010	−0.05580	0.0350*
H6	0.51310	0.18990	−0.14880	0.0360*
H7	0.53100	0.43540	−0.13300	0.0350*
H8	0.53690	0.53110	−0.02370	0.0310*
H21	0.772 (4)	0.714 (3)	0.0527 (14)	0.052 (7)*
H21A	0.79600	0.85900	0.14180	0.0200*
H31	0.848 (3)	0.510 (2)	0.2353 (12)	0.039 (6)*
H31A	0.80150	0.76100	0.24900	0.0220*
H41	1.249 (4)	0.820 (3)	0.1950 (13)	0.058 (7)*
H1W	0.257 (3)	0.702 (2)	0.0540 (11)	0.031 (6)*
H2W	0.076 (4)	0.713 (3)	0.0479 (12)	0.043 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0236 (7)	0.0219 (7)	0.0229 (7)	−0.0035 (6)	−0.0003 (6)	−0.0039 (5)
C2	0.0243 (8)	0.0383 (9)	0.0189 (7)	−0.0037 (8)	0.0000 (7)	−0.0031 (7)
C3	0.0305 (9)	0.0346 (9)	0.0230 (8)	−0.0026 (8)	−0.0005 (7)	0.0089 (7)
C4	0.0317 (10)	0.0224 (8)	0.0322 (9)	−0.0019 (7)	0.0013 (8)	0.0056 (7)
C5	0.0337 (10)	0.0216 (8)	0.0310 (9)	0.0000 (7)	0.0027 (8)	−0.0058 (7)
C6	0.0331 (10)	0.0374 (9)	0.0204 (8)	−0.0021 (8)	0.0030 (7)	−0.0062 (7)
C7	0.0316 (9)	0.0323 (8)	0.0230 (8)	0.0006 (8)	0.0007 (8)	0.0078 (7)
C8	0.0276 (9)	0.0198 (7)	0.0293 (9)	−0.0010 (7)	0.0019 (8)	0.0034 (6)
C9	0.0179 (7)	0.0216 (7)	0.0208 (7)	−0.0011 (6)	0.0004 (6)	−0.0001 (6)
C10	0.0208 (7)	0.0210 (7)	0.0241 (8)	0.0004 (7)	0.0011 (6)	−0.0003 (6)
O11	0.0143 (5)	0.0222 (5)	0.0248 (6)	−0.0001 (5)	0.0016 (4)	−0.0053 (4)
O12	0.0164 (5)	0.0246 (5)	0.0208 (5)	0.0011 (5)	−0.0029 (4)	−0.0042 (4)
O21	0.0164 (5)	0.0339 (6)	0.0151 (5)	0.0057 (5)	0.0014 (4)	0.0004 (5)
O31	0.0178 (6)	0.0285 (6)	0.0324 (7)	−0.0029 (5)	−0.0029 (5)	0.0134 (6)
O41	0.0136 (5)	0.0221 (5)	0.0289 (6)	−0.0003 (5)	0.0009 (4)	−0.0033 (5)
O42	0.0192 (6)	0.0281 (6)	0.0439 (8)	0.0028 (5)	0.0010 (5)	0.0094 (6)
C11	0.0140 (7)	0.0174 (6)	0.0162 (7)	0.0004 (6)	−0.0014 (6)	0.0052 (6)
C21	0.0150 (7)	0.0181 (7)	0.0178 (7)	0.0008 (6)	0.0026 (6)	0.0019 (6)
C31	0.0142 (6)	0.0241 (7)	0.0166 (7)	−0.0009 (6)	−0.0001 (5)	0.0003 (6)
C41	0.0161 (7)	0.0243 (7)	0.0131 (7)	−0.0003 (7)	−0.0002 (5)	0.0003 (6)
O1W	0.0167 (6)	0.0490 (8)	0.0187 (6)	0.0028 (6)	−0.0003 (5)	0.0079 (6)

Geometric parameters (Å, º)

O11—C11	1.2547 (18)	C5—C6	1.359 (3)
O12—C11	1.2499 (18)	C6—C7	1.415 (3)
O21—C21	1.4142 (19)	C7—C8	1.362 (2)
O31—C31	1.410 (2)	C8—C9	1.409 (2)
O41—C41	1.3116 (19)	C9—C10	1.416 (2)
O42—C41	1.210 (2)	C2—H2	0.9500
O21—H21	0.86 (3)	C3—H3	0.9500
O31—H31	0.84 (2)	C4—H4	0.9500
O41—H41	0.90 (3)	C5—H5	0.9500
O1W—H2W	0.84 (3)	C6—H6	0.9500
O1W—H1W	0.82 (2)	C7—H7	0.9500
N1—C9	1.370 (2)	C8—H8	0.9500
N1—C2	1.324 (2)	C11—C21	1.542 (2)
N1—H1	0.880 (19)	C21—C31	1.524 (2)
C2—C3	1.396 (3)	C31—C41	1.531 (2)
C3—C4	1.370 (2)	C21—H21A	0.970
C4—C10	1.415 (2)	C31—H31A	0.970
C5—C10	1.415 (2)
C21—O21—H21	107.0 (19)	C10—C5—H5	120.00
C31—O31—H31	108.2 (14)	C6—C5—H5	120.00
C41—O41—H41	119.0 (18)	C7—C6—H6	120.00
H1W—O1W—H2W	106 (2)	C5—C6—H6	120.00
C2—N1—C9	123.32 (14)	C6—C7—H7	120.00
C9—N1—H1	119.5 (14)	C8—C7—H7	120.00
C2—N1—H1	117.0 (14)	C7—C8—H8	121.00
N1—C2—C3	120.54 (15)	C9—C8—H8	121.00
C2—C3—C4	118.97 (16)	O11—C11—C21	115.98 (13)
C3—C4—C10	120.77 (16)	O12—C11—C21	118.17 (13)
C6—C5—C10	120.53 (16)	O11—C11—O12	125.84 (14)
C5—C6—C7	120.61 (16)	O21—C21—C11	111.54 (12)
C6—C7—C8	120.89 (16)	C11—C21—C31	108.68 (12)
C7—C8—C9	118.96 (15)	O21—C21—C31	109.51 (12)
N1—C9—C10	118.22 (14)	C21—C31—C41	111.87 (12)
C8—C9—C10	121.04 (14)	O31—C31—C41	110.47 (13)
N1—C9—C8	120.74 (14)	O31—C31—C21	109.73 (12)
C5—C10—C9	117.96 (14)	O41—C41—C31	112.52 (13)
C4—C10—C9	118.18 (14)	O42—C41—C31	121.12 (14)
C4—C10—C5	123.86 (15)	O41—C41—O42	126.33 (14)
N1—C2—H2	120.00	C11—C21—H21A	109.00
C3—C2—H2	120.00	C31—C21—H21A	109.00
C4—C3—H3	121.00	O21—C21—H21A	109.00
C2—C3—H3	121.00	C21—C31—H31A	108.00
C3—C4—H4	120.00	C41—C31—H31A	108.00
C10—C4—H4	120.00	O31—C31—H31A	108.00
C9—N1—C2—C3	0.3 (2)	N1—C9—C10—C5	179.09 (15)
C2—N1—C9—C8	−179.92 (15)	C8—C9—C10—C4	−180.00 (15)
C2—N1—C9—C10	−0.1 (2)	C8—C9—C10—C5	−1.1 (2)
N1—C2—C3—C4	−0.7 (3)	O11—C11—C21—O21	−170.33 (13)
C2—C3—C4—C10	0.8 (3)	O11—C11—C21—C31	68.84 (17)
C3—C4—C10—C9	−0.5 (3)	O12—C11—C21—O21	8.28 (19)
C3—C4—C10—C5	−179.42 (19)	O12—C11—C21—C31	−112.54 (15)
C6—C5—C10—C9	0.4 (3)	O21—C21—C31—O31	−70.63 (15)
C10—C5—C6—C7	0.6 (3)	O21—C21—C31—C41	52.34 (16)
C6—C5—C10—C4	179.3 (2)	C11—C21—C31—O31	51.43 (16)
C5—C6—C7—C8	−1.1 (3)	C11—C21—C31—C41	174.41 (12)
C6—C7—C8—C9	0.4 (3)	O31—C31—C41—O41	178.61 (12)
C7—C8—C9—C10	0.6 (2)	O31—C31—C41—O42	−3.1 (2)
C7—C8—C9—N1	−179.50 (16)	C21—C31—C41—O41	56.05 (17)
N1—C9—C10—C4	0.2 (2)	C21—C31—C41—O42	−125.65 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O12	0.880 (19)	1.797 (19)	2.6635 (18)	168 (2)
O1W—H1W···O12	0.82 (2)	1.88 (2)	2.6888 (17)	171 (2)
O1W—H2W···O21^i	0.84 (3)	1.95 (3)	2.7832 (17)	170 (3)
O21—H21···O1W^ii	0.86 (3)	1.81 (3)	2.6665 (17)	172 (3)
O31—H31···O42	0.84 (2)	2.17 (2)	2.6652 (17)	117.7 (17)
O31—H31···O41^iii	0.84 (2)	2.28 (2)	2.9480 (17)	136.4 (19)
O41—H41···O11^iv	0.90 (3)	1.61 (3)	2.5090 (16)	180 (4)
C2—H2···O11^v	0.95	2.28	3.1263 (19)	148
C5—H5···O21^vi	0.95	2.59	3.452 (2)	151

Symmetry codes: (i) x−1, y, z; (ii) x+1/2, −y+3/2, −z; (iii) −x+2, y−1/2, −z+1/2; (iv) x+1, y, z; (v) −x+1, y−1/2, −z+1/2; (vi) x−1/2, −y+1/2, −z.

(II) bis(quinolinium-2-carboxylate) (2R,3R)-tartaric acid

Crystal data

2C10H7NO2·C4H6O6	Z = 1
Mr = 496.42	F(000) = 258
Triclinic, P1	Dx = 1.482 Mg m^−3
Hall symbol: P 1	Melting point = 469.1–470.7 K
a = 4.9730 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.446 (3) Å	Cell parameters from 2448 reflections
c = 11.655 (4) Å	θ = 2.4–27.5°
α = 100.950 (5)°	µ = 0.12 mm^−1
β = 98.903 (6)°	T = 130 K
γ = 106.388 (5)°	Cut block, yellow
V = 556.2 (3) Å^3	0.50 × 0.40 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2517 independent reflections
Radiation source: sealed tube	2481 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.012
ϕ and ω scans	θmax = 27.3°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −6→5
Tmin = 0.95, Tmax = 0.97	k = −13→13
3500 measured reflections	l = −9→15

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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.105	w = 1/[σ^2(Fo^2) + (0.0695P)^2 + 0.0367P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
2517 reflections	Δρmax = 0.17 e Å^−3
321 parameters	Δρmin = −0.26 e Å^−3
3 restraints	Absolute structure: Flack (1983), ? Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.4 (6)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 (Ų)

	x	y	z	Uiso*/Ueq
O22	0.8830 (4)	0.84011 (17)	0.65635 (18)	0.0278 (5)
O23	1.0568 (4)	1.07037 (17)	0.68872 (17)	0.0272 (5)
N1	0.4157 (4)	0.8328 (2)	0.50139 (18)	0.0191 (6)
C2	0.6231 (5)	0.9537 (2)	0.5486 (2)	0.0186 (6)
C3	0.6038 (5)	1.0720 (2)	0.5134 (2)	0.0211 (7)
C4	0.3654 (5)	1.0638 (2)	0.4314 (2)	0.0205 (7)
C5	−0.1102 (5)	0.9204 (2)	0.2980 (2)	0.0217 (7)
C6	−0.3143 (5)	0.7941 (3)	0.2527 (2)	0.0242 (7)
C7	−0.2775 (5)	0.6769 (3)	0.2890 (2)	0.0269 (7)
C8	−0.0385 (5)	0.6871 (2)	0.3708 (2)	0.0253 (7)
C9	0.1737 (5)	0.8178 (2)	0.4180 (2)	0.0198 (7)
C10	0.1440 (5)	0.9363 (2)	0.3823 (2)	0.0189 (7)
C22	0.8780 (5)	0.9529 (2)	0.6402 (2)	0.0204 (6)
O22A	0.3800 (4)	0.57270 (18)	0.52665 (19)	0.0323 (6)
O23A	0.1239 (4)	0.36225 (17)	0.53635 (16)	0.0251 (5)
N1A	0.8137 (4)	0.5796 (2)	0.69666 (18)	0.0186 (6)
C2A	0.5888 (5)	0.4654 (2)	0.6597 (2)	0.0187 (6)
C3A	0.5862 (5)	0.3509 (2)	0.7063 (2)	0.0199 (7)
C4A	0.8187 (5)	0.3582 (2)	0.7903 (2)	0.0217 (7)
C5A	1.3026 (5)	0.4952 (3)	0.9195 (2)	0.0237 (7)
C6A	1.5259 (5)	0.6165 (3)	0.9529 (2)	0.0269 (8)
C7A	1.5176 (5)	0.7286 (3)	0.9016 (2)	0.0276 (7)
C8A	1.2833 (5)	0.7186 (2)	0.8169 (2)	0.0235 (7)
C9A	1.0518 (5)	0.5944 (2)	0.7816 (2)	0.0191 (6)
C10A	1.0572 (5)	0.4807 (2)	0.8309 (2)	0.0206 (7)
C22A	0.3413 (5)	0.4680 (2)	0.5650 (2)	0.0203 (6)
O11	0.4333 (4)	0.10178 (19)	−0.12725 (16)	0.0269 (5)
O12	0.0776 (4)	0.01390 (19)	−0.03946 (17)	0.0303 (5)
O21	0.4331 (4)	0.04090 (18)	0.16338 (17)	0.0241 (5)
O31	0.4820 (4)	0.32587 (18)	0.12343 (17)	0.0245 (5)
O41	0.7885 (4)	0.34036 (18)	0.33864 (16)	0.0231 (5)
O42	1.0930 (4)	0.24772 (19)	0.26005 (17)	0.0287 (5)
C11	0.3287 (5)	0.0675 (2)	−0.0378 (2)	0.0209 (6)
C21	0.5594 (5)	0.1006 (2)	0.0771 (2)	0.0201 (6)
C31	0.6905 (5)	0.2591 (2)	0.1253 (2)	0.0205 (7)
C41	0.8806 (5)	0.2837 (2)	0.2495 (2)	0.0198 (6)
H1	0.439	0.753	0.516	0.022*
H3	0.75400	1.15720	0.54580	0.0250*
H4	0.34920	1.14390	0.40760	0.0250*
H5	−0.13800	0.99810	0.27310	0.0260*
H6	−0.48260	0.78430	0.19600	0.0290*
H7	−0.42290	0.59300	0.25620	0.0320*
H8	−0.01690	0.60770	0.39430	0.0300*
H1A	0.805	0.644	0.668	0.017*
H3A	0.42500	0.26930	0.67990	0.0240*
H4A	0.82020	0.28070	0.82160	0.0260*
H5A	1.31140	0.42150	0.95510	0.0280*
H6A	1.69010	0.62590	1.01170	0.0320*
H7A	1.67610	0.81140	0.92620	0.0330*
H8A	1.27710	0.79370	0.78280	0.0280*
H11	0.284	0.090	−0.186	0.045*
H21	0.268	0.035	0.150	0.051*
H31	0.375	0.298	0.167	0.048*
H41	0.917	0.345	0.406	0.053*
H211	0.71100	0.06230	0.05910	0.0240*
H311	0.81620	0.29330	0.07330	0.0250*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O22	0.0282 (9)	0.0181 (8)	0.0305 (10)	0.0033 (7)	−0.0048 (7)	0.0058 (7)
O23	0.0265 (9)	0.0187 (8)	0.0257 (10)	−0.0032 (7)	−0.0055 (7)	0.0052 (7)
N1	0.0195 (10)	0.0150 (9)	0.0204 (10)	0.0041 (8)	0.0015 (8)	0.0030 (8)
C2	0.0183 (11)	0.0191 (11)	0.0163 (11)	0.0043 (9)	0.0043 (9)	0.0014 (9)
C3	0.0249 (12)	0.0158 (11)	0.0192 (12)	0.0032 (9)	0.0055 (9)	0.0006 (9)
C4	0.0232 (11)	0.0173 (11)	0.0219 (12)	0.0077 (9)	0.0064 (9)	0.0038 (9)
C5	0.0246 (12)	0.0227 (11)	0.0193 (12)	0.0117 (10)	0.0035 (9)	0.0038 (9)
C6	0.0204 (12)	0.0287 (12)	0.0201 (13)	0.0081 (10)	0.0001 (9)	0.0011 (10)
C7	0.0236 (13)	0.0217 (12)	0.0262 (13)	0.0020 (10)	−0.0024 (10)	−0.0013 (10)
C8	0.0267 (13)	0.0178 (11)	0.0268 (13)	0.0044 (10)	0.0008 (10)	0.0029 (10)
C9	0.0192 (11)	0.0201 (11)	0.0184 (12)	0.0058 (9)	0.0032 (9)	0.0022 (9)
C10	0.0200 (11)	0.0188 (11)	0.0174 (12)	0.0063 (9)	0.0050 (9)	0.0023 (9)
C22	0.0200 (11)	0.0207 (11)	0.0172 (11)	0.0031 (9)	0.0034 (8)	0.0030 (9)
O22A	0.0322 (10)	0.0190 (8)	0.0353 (11)	0.0007 (7)	−0.0098 (8)	0.0080 (8)
O23A	0.0217 (8)	0.0215 (8)	0.0231 (9)	−0.0025 (7)	−0.0026 (7)	0.0048 (7)
N1A	0.0204 (10)	0.0148 (9)	0.0198 (11)	0.0052 (8)	0.0030 (8)	0.0043 (8)
C2A	0.0186 (11)	0.0180 (11)	0.0166 (11)	0.0043 (9)	0.0044 (8)	−0.0005 (8)
C3A	0.0183 (11)	0.0150 (10)	0.0232 (13)	0.0024 (8)	0.0051 (9)	0.0014 (9)
C4A	0.0250 (12)	0.0191 (11)	0.0233 (12)	0.0084 (9)	0.0083 (9)	0.0062 (9)
C5A	0.0243 (12)	0.0266 (12)	0.0209 (12)	0.0117 (10)	0.0039 (9)	0.0034 (10)
C6A	0.0233 (13)	0.0335 (14)	0.0212 (13)	0.0128 (11)	0.0004 (10)	−0.0014 (11)
C7A	0.0222 (12)	0.0227 (12)	0.0290 (14)	0.0023 (10)	0.0016 (10)	−0.0040 (10)
C8A	0.0224 (12)	0.0184 (11)	0.0261 (13)	0.0044 (9)	0.0040 (10)	0.0018 (9)
C9A	0.0185 (11)	0.0182 (10)	0.0180 (12)	0.0050 (9)	0.0032 (9)	0.0004 (9)
C10A	0.0198 (11)	0.0225 (12)	0.0201 (12)	0.0095 (9)	0.0056 (9)	0.0018 (9)
C22A	0.0210 (11)	0.0181 (10)	0.0188 (11)	0.0064 (9)	0.0012 (9)	−0.0001 (9)
O11	0.0222 (9)	0.0322 (10)	0.0201 (9)	0.0004 (7)	0.0009 (7)	0.0074 (8)
O12	0.0184 (8)	0.0362 (10)	0.0270 (10)	−0.0007 (8)	0.0024 (7)	0.0025 (8)
O21	0.0244 (9)	0.0238 (8)	0.0234 (9)	0.0051 (7)	0.0055 (7)	0.0081 (7)
O31	0.0249 (9)	0.0233 (8)	0.0260 (9)	0.0102 (7)	0.0021 (7)	0.0066 (7)
O41	0.0216 (8)	0.0237 (8)	0.0193 (9)	0.0055 (7)	−0.0002 (7)	0.0007 (7)
O42	0.0229 (9)	0.0355 (9)	0.0283 (10)	0.0119 (8)	0.0031 (7)	0.0074 (8)
C11	0.0210 (11)	0.0166 (10)	0.0221 (12)	0.0052 (9)	0.0024 (9)	0.0007 (9)
C21	0.0206 (11)	0.0203 (11)	0.0194 (11)	0.0065 (9)	0.0052 (9)	0.0042 (9)
C31	0.0179 (11)	0.0200 (11)	0.0209 (12)	0.0027 (8)	0.0032 (9)	0.0048 (9)
C41	0.0174 (10)	0.0159 (10)	0.0227 (12)	0.0021 (8)	0.0011 (8)	0.0044 (9)

Geometric parameters (Å, º)

O22—C22	1.234 (3)	C9—C10	1.417 (3)
O23—C22	1.258 (3)	C3—H3	0.9500
O22A—C22A	1.236 (3)	C4—H4	0.9500
O23A—C22A	1.255 (3)	C5—H5	0.9500
O11—C11	1.300 (3)	C6—H6	0.9500
O12—C11	1.211 (3)	C7—H7	0.9300
O21—C21	1.417 (3)	C8—H8	0.9500
O31—C31	1.403 (3)	C2A—C3A	1.402 (3)
O41—C41	1.306 (3)	C2A—C22A	1.531 (3)
O42—C41	1.214 (3)	C3A—C4A	1.369 (3)
O11—H11	0.89	C4A—C10A	1.417 (3)
O21—H21	0.79	C5A—C6A	1.369 (4)
O31—H31	0.82	C5A—C10A	1.423 (3)
O41—H41	0.92	C6A—C7A	1.420 (4)
N1—C9	1.375 (3)	C7A—C8A	1.371 (3)
N1—C2	1.337 (3)	C8A—C9A	1.409 (3)
N1—H1	0.92	C9A—C10A	1.419 (3)
N1A—C9A	1.372 (3)	C3A—H3A	0.9500
N1A—C2A	1.328 (3)	C4A—H4A	0.9500
N1A—H1A	0.81	C5A—H5A	0.9500
C2—C22	1.529 (3)	C6A—H6A	0.9500
C2—C3	1.397 (3)	C7A—H7A	0.9500
C3—C4	1.374 (3)	C8A—H8A	0.9500
C4—C10	1.415 (3)	C11—C21	1.534 (3)
C5—C6	1.365 (4)	C21—C31	1.551 (3)
C5—C10	1.423 (3)	C31—C41	1.534 (3)
C6—C7	1.418 (4)	C21—H211	0.9800
C7—C8	1.368 (4)	C31—H311	0.9800
C8—C9	1.415 (3)
C11—O11—H11	107	C3A—C4A—C10A	120.4 (2)
C21—O21—H21	108	C6A—C5A—C10A	119.3 (2)
C31—O31—H31	109	C5A—C6A—C7A	121.5 (2)
C41—O41—H41	105	C6A—C7A—C8A	120.7 (2)
C2—N1—C9	122.7 (2)	C7A—C8A—C9A	118.5 (2)
C2—N1—H1	121	N1A—C9A—C10A	117.9 (2)
C9—N1—H1	116	N1A—C9A—C8A	120.5 (2)
C2A—N1A—C9A	123.3 (2)	C8A—C9A—C10A	121.7 (2)
C2A—N1A—H1A	117	C5A—C10A—C9A	118.3 (2)
C9A—N1A—H1A	120	C4A—C10A—C5A	122.9 (2)
N1—C2—C3	120.7 (2)	C4A—C10A—C9A	118.8 (2)
C3—C2—C22	123.1 (2)	O23A—C22A—C2A	115.13 (19)
N1—C2—C22	116.18 (19)	O22A—C22A—O23A	128.4 (2)
C2—C3—C4	119.3 (2)	O22A—C22A—C2A	116.5 (2)
C3—C4—C10	120.1 (2)	C2A—C3A—H3A	120.00
C6—C5—C10	120.4 (2)	C4A—C3A—H3A	120.00
C5—C6—C7	120.7 (2)	C3A—C4A—H4A	120.00
C6—C7—C8	121.2 (2)	C10A—C4A—H4A	120.00
C7—C8—C9	118.4 (2)	C6A—C5A—H5A	120.00
N1—C9—C8	120.2 (2)	C10A—C5A—H5A	120.00
N1—C9—C10	118.1 (2)	C7A—C6A—H6A	119.00
C8—C9—C10	121.7 (2)	C5A—C6A—H6A	119.00
C4—C10—C9	119.1 (2)	C6A—C7A—H7A	120.00
C4—C10—C5	123.2 (2)	C8A—C7A—H7A	120.00
C5—C10—C9	117.7 (2)	C9A—C8A—H8A	121.00
O22—C22—C2	117.2 (2)	C7A—C8A—H8A	121.00
O23—C22—C2	113.87 (19)	O11—C11—C21	113.3 (2)
O22—C22—O23	129.0 (2)	O12—C11—C21	120.5 (2)
C4—C3—H3	120.00	O11—C11—O12	126.2 (2)
C2—C3—H3	120.00	O21—C21—C11	109.3 (2)
C10—C4—H4	120.00	O21—C21—C31	110.39 (18)
C3—C4—H4	120.00	C11—C21—C31	109.14 (18)
C6—C5—H5	120.00	O31—C31—C21	112.9 (2)
C10—C5—H5	120.00	O31—C31—C41	114.68 (19)
C7—C6—H6	119.00	C21—C31—C41	105.98 (17)
C5—C6—H6	120.00	O41—C41—C31	114.6 (2)
C8—C7—H7	121.00	O42—C41—C31	120.6 (2)
C6—C7—H7	118.00	O41—C41—O42	124.8 (2)
C9—C8—H8	121.00	O21—C21—H211	109.00
C7—C8—H8	120.00	C11—C21—H211	109.00
C3A—C2A—C22A	123.5 (2)	C31—C21—H211	109.00
N1A—C2A—C3A	120.5 (2)	O31—C31—H311	108.00
N1A—C2A—C22A	116.07 (19)	C21—C31—H311	108.00
C2A—C3A—C4A	119.2 (2)	C41—C31—H311	108.00
C9—N1—C2—C3	−0.8 (4)	N1A—C2A—C22A—O22A	4.1 (3)
C9—N1—C2—C22	180.0 (2)	N1A—C2A—C22A—O23A	−176.0 (2)
C2—N1—C9—C8	179.8 (2)	C3A—C2A—C22A—O22A	−175.7 (2)
C2—N1—C9—C10	−0.7 (3)	C3A—C2A—C22A—O23A	4.3 (3)
C2A—N1A—C9A—C8A	−180.0 (2)	C2A—C3A—C4A—C10A	0.9 (4)
C2A—N1A—C9A—C10A	0.7 (3)	C3A—C4A—C10A—C5A	178.9 (2)
C9A—N1A—C2A—C3A	−0.8 (4)	C3A—C4A—C10A—C9A	−0.9 (4)
C9A—N1A—C2A—C22A	179.5 (2)	C10A—C5A—C6A—C7A	0.4 (4)
C3—C2—C22—O22	−173.8 (2)	C6A—C5A—C10A—C4A	179.2 (2)
N1—C2—C22—O22	5.4 (3)	C6A—C5A—C10A—C9A	−1.0 (4)
N1—C2—C22—O23	−174.9 (2)	C5A—C6A—C7A—C8A	0.3 (4)
N1—C2—C3—C4	1.5 (4)	C6A—C7A—C8A—C9A	−0.3 (4)
C22—C2—C3—C4	−179.3 (2)	C7A—C8A—C9A—N1A	−179.7 (2)
C3—C2—C22—O23	5.8 (3)	C7A—C8A—C9A—C10A	−0.4 (4)
C2—C3—C4—C10	−0.8 (4)	N1A—C9A—C10A—C4A	0.1 (3)
C3—C4—C10—C9	−0.7 (4)	N1A—C9A—C10A—C5A	−179.7 (2)
C3—C4—C10—C5	179.3 (2)	C8A—C9A—C10A—C4A	−179.2 (2)
C6—C5—C10—C4	179.1 (2)	C8A—C9A—C10A—C5A	1.0 (4)
C6—C5—C10—C9	−0.9 (4)	O11—C11—C21—O21	−170.93 (19)
C10—C5—C6—C7	0.2 (4)	O11—C11—C21—C31	68.3 (3)
C5—C6—C7—C8	0.5 (4)	O12—C11—C21—O21	8.7 (3)
C6—C7—C8—C9	−0.5 (4)	O12—C11—C21—C31	−112.2 (2)
C7—C8—C9—N1	179.3 (2)	O21—C21—C31—O31	−75.5 (2)
C7—C8—C9—C10	−0.2 (4)	O21—C21—C31—C41	50.8 (3)
N1—C9—C10—C5	−178.6 (2)	C11—C21—C31—O31	44.6 (3)
C8—C9—C10—C4	−179.1 (2)	C11—C21—C31—C41	170.9 (2)
C8—C9—C10—C5	0.9 (4)	O31—C31—C41—O41	12.6 (3)
N1—C9—C10—C4	1.4 (3)	O31—C31—C41—O42	−169.6 (2)
N1A—C2A—C3A—C4A	−0.1 (4)	C21—C31—C41—O41	−112.7 (2)
C22A—C2A—C3A—C4A	179.6 (2)	C21—C31—C41—O42	65.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O22	0.92	2.36	2.686 (3)	101
N1—H1···O22A	0.92	1.85	2.747 (3)	164
N1A—H1A···O22	0.81	2.01	2.784 (3)	159
N1A—H1A···O22A	0.81	2.30	2.668 (3)	108
O11—H11···O23^i	0.89	1.64	2.521 (3)	168
O21—H21···O12	0.79	2.21	2.639 (3)	115
O31—H31···O42^ii	0.82	1.92	2.739 (3)	172
O41—H41···O23A^iii	0.92	1.65	2.557 (3)	173
C3—H3···O23A^iv	0.95	2.43	3.318 (3)	155
C3A—H3A···O23^v	0.95	2.38	3.288 (3)	159
C4—H4···O42^vi	0.95	2.56	3.406 (3)	148
C4A—H4A···O11^vii	0.95	2.51	3.228 (3)	132
C5—H5···O21^vi	0.95	2.51	3.235 (3)	133
C5—H5···O42^vi	0.95	2.58	3.416 (3)	147
C5A—H5A···O31^viii	0.95	2.50	3.377 (3)	153
C7A—H7A···O12^ix	0.95	2.38	3.325 (4)	172
C8—H8···O22A	0.95	2.47	3.181 (3)	132
C8—H8···O41^ii	0.95	2.60	3.410 (3)	144
C8A—H8A···O22	0.95	2.48	3.202 (3)	132
C21—H211···O12^iii	0.98	2.42	3.353 (3)	159

Symmetry codes: (i) x−1, y−1, z−1; (ii) x−1, y, z; (iii) x+1, y, z; (iv) x+1, y+1, z; (v) x−1, y−1, z; (vi) x−1, y+1, z; (vii) x, y, z+1; (viii) x+1, y, z+1; (ix) x+2, y+1, z+1.