Download citation
Download citation
link to html
In the title compound, C9H8N+·C6H7O7, the dihydrogen citrate anions form a convoluted two-dimensional hydrogen-bonded substructure through head-to-tail inter­actions with the inter­stitial π-stacked quinolinium cations linked to it peripherally through cyclic R12(5) N+—H...O(carbox­yl/hydrox­yl) hydrogen-bond inter­actions. The loss of a proton from one of the β-carboxylic acid groups of the citric acid generates a chiral centre in the anion, but these form a racemate in the centrosymmetric crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807022106/bt2355sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807022106/bt2355Isup2.hkl
Contains datablock I

CCDC reference: 651427

Key indicators

  • Single-crystal X-ray study
  • T = 130 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.032
  • wR factor = 0.091
  • Data-to-parameter ratio = 12.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C4 - C10 .. 18.91 su PLAT230_ALERT_2_B Hirshfeld Test Diff for C5 - C6 .. 19.45 su
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C5 PLAT432_ALERT_2_C Short Inter X...Y Contact O11 .. C2 .. 3.00 Ang.
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C31 = ... R
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The structures of the quinolinium carboxylates and sulfonates are not prevalent in the crystallographic literature and most of the examples are 1:1 salts, mainly with the aromatic acids e.g. 5-sulfosalicylic acid (Smith et al., 2004), 3,5-dinitrosalicylic acid (Smith, Wermuth & White, 2006), and picrylsulfonic acid (Smith, Wermuth & Healy, 2006). These compounds often feature π-associated cation-anion stacks with peripheral hydrogen bonding giving three-dimensional framework structures. With the quinolinium salts of the aliphatic carboxylic acids, most examples are anhydrous acid salts of polyprotic analogues, e.g. fumaric acid (Shan et al., 2003) and L-tartaric acid (Smith et al., (2006). The 1:1 stoichiometric reaction of quinoline with citric acid in isopropyl alcohol was expected to give a similar acid citrate and this was confirmed in the structure determination of C9H8N+ C6H7O7- (I), reported here.

Figure 1 shows the quinolinium cation and the dihydrogen citrate anion in which one of the β-carboxylic acid groups rather than the α-group has lost the proton. It is more usual for the α-group to be associated with the first dissociation constant (Tapscott, 1982) and is seen in typical structures such as sodium dihydrogen citrate (Glusker et al., 1965), and sildenafil dihydrogen citrate (Yathirajan et al., 2005). In (I), this results in the generation a chiral centre at C31 in the anion species but these form a racemete in the centrosymmetric crystal. These anions form a convoluted two-dimensional hydrogen-bonded substructure through head-to-tail carboxylic acid···carboxylate interactions, one linear, the other three-centred cyclic [R21(4)] (Table 1). The partially overlapping quinolinium cations [C5–C10: minimum ring centroid and perpendicular separations of 3.840 (1) and 3.560 (1) Å respectively] form π-associated stacks which extend down the a cell direction. The anion substructures accommodate these stacks (Fig. 2). which are linked to the anionic substructure by symmetric three-centre R21(5) N+H···O(carboxyl, hydroxyl) hydrogen-bonding associations. The result is a three-dimensional framework structure which in addition has 66.8 Å3 potential solvent accessible voids.

The conformation of the dihydrogen citrate anions is maintained by the presence of an intramolecular hydroxyl–carboxyl hydrogen bond [O31—H···O12, 2.6337 (13) Å].

Related literature top

There is a similarity between the structure of the title compound and those of the quinolinium hydrogen salts of fumaric acid (Shan et al., 2003) and L-tartaric acid (Smith, Wermuth & White, 2006).

For related literature, see: Glusker et al. (1965); Smith et al. (2004, 2007); Smith, Wermuth & Healy (2006); Tapscott (1982); Yathirajan et al. (2005).

Experimental top

Compound (I) was synthesized by heating 1 mmol quantities of citric acid and quinoline in 50 ml of 2-propanol for 10 min under reflux. Colourless needles (m.p. 403 K) were obtained after partial room-temperature evaporation of solvent.

Refinement top

Hydrogen atoms potentially involved in hydrogen-bonding interactions were located by difference methods and their positional and isotropic displacement parameters were refined. Other H atoms were included in the refinement at calculated positions [C—H (aromatic) = 0.95 Å and C–H (aliphatic) = 0.99 Å] using a riding-model approximation with Uiso(H) = 1.2Ueq(C).

Structure description top

The structures of the quinolinium carboxylates and sulfonates are not prevalent in the crystallographic literature and most of the examples are 1:1 salts, mainly with the aromatic acids e.g. 5-sulfosalicylic acid (Smith et al., 2004), 3,5-dinitrosalicylic acid (Smith, Wermuth & White, 2006), and picrylsulfonic acid (Smith, Wermuth & Healy, 2006). These compounds often feature π-associated cation-anion stacks with peripheral hydrogen bonding giving three-dimensional framework structures. With the quinolinium salts of the aliphatic carboxylic acids, most examples are anhydrous acid salts of polyprotic analogues, e.g. fumaric acid (Shan et al., 2003) and L-tartaric acid (Smith et al., (2006). The 1:1 stoichiometric reaction of quinoline with citric acid in isopropyl alcohol was expected to give a similar acid citrate and this was confirmed in the structure determination of C9H8N+ C6H7O7- (I), reported here.

Figure 1 shows the quinolinium cation and the dihydrogen citrate anion in which one of the β-carboxylic acid groups rather than the α-group has lost the proton. It is more usual for the α-group to be associated with the first dissociation constant (Tapscott, 1982) and is seen in typical structures such as sodium dihydrogen citrate (Glusker et al., 1965), and sildenafil dihydrogen citrate (Yathirajan et al., 2005). In (I), this results in the generation a chiral centre at C31 in the anion species but these form a racemete in the centrosymmetric crystal. These anions form a convoluted two-dimensional hydrogen-bonded substructure through head-to-tail carboxylic acid···carboxylate interactions, one linear, the other three-centred cyclic [R21(4)] (Table 1). The partially overlapping quinolinium cations [C5–C10: minimum ring centroid and perpendicular separations of 3.840 (1) and 3.560 (1) Å respectively] form π-associated stacks which extend down the a cell direction. The anion substructures accommodate these stacks (Fig. 2). which are linked to the anionic substructure by symmetric three-centre R21(5) N+H···O(carboxyl, hydroxyl) hydrogen-bonding associations. The result is a three-dimensional framework structure which in addition has 66.8 Å3 potential solvent accessible voids.

The conformation of the dihydrogen citrate anions is maintained by the presence of an intramolecular hydroxyl–carboxyl hydrogen bond [O31—H···O12, 2.6337 (13) Å].

There is a similarity between the structure of the title compound and those of the quinolinium hydrogen salts of fumaric acid (Shan et al., 2003) and L-tartaric acid (Smith, Wermuth & White, 2006).

For related literature, see: Glusker et al. (1965); Smith et al. (2004, 2007); Smith, Wermuth & Healy (2006); Tapscott (1982); Yathirajan et al. (2005).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); 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: PLATON.

Figures top
[Figure 1] Fig. 1. The molecular configuration and atom-numbering scheme for the quinolinium cation and the dihydrogen citrate anion in (I). Non-H atoms are shown as 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. A perspective view of the packing of (I) in the unit cell viewed down the approximate a axial direction, showing the π-stacked quinolinium cations inside the citrate convoluted sheet substructures. Hydrogen-bonding interactions are shown as dashed lines and non- interactive hydrogen atoms are omitted: symmetry codes: (iii) x + 1, y, z; (iv) -x - 1/2, y - 3/2, -z + 1/2; For other codes see Table 1.
quinolinium dihydrogen citrate top
Crystal data top
C9H8N+·C6H7O7F(000) = 672
Mr = 321.28Dx = 1.390 Mg m3
Monoclinic, P21/nMelting point: 403 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 7.5202 (6) ÅCell parameters from 4204 reflections
b = 11.9267 (10) Åθ = 2.9–27.5°
c = 17.1484 (14) ŵ = 0.11 mm1
β = 93.217 (1)°T = 130 K
V = 1535.6 (2) Å3Cut block, colourless
Z = 40.50 × 0.35 × 0.30 mm
Data collection top
Bruker SMART CCD detector
diffractometer
2695 independent reflections
Radiation source: sealed tube2431 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
φ and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
h = 88
Tmin = 0.95, Tmax = 0.97k = 1214
7847 measured reflectionsl = 2020
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)] = 0.032H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.092 w = 1/[σ2(Fo2) + (0.0491P)2 + 0.223P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
2695 reflectionsΔρmax = 0.18 e Å3
225 parametersΔρmin = 0.15 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0085 (16)
Crystal data top
C9H8N+·C6H7O7V = 1535.6 (2) Å3
Mr = 321.28Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.5202 (6) ŵ = 0.11 mm1
b = 11.9267 (10) ÅT = 130 K
c = 17.1484 (14) Å0.50 × 0.35 × 0.30 mm
β = 93.217 (1)°
Data collection top
Bruker SMART CCD detector
diffractometer
2695 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
2431 reflections with I > 2σ(I)
Tmin = 0.95, Tmax = 0.97Rint = 0.020
7847 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.092H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.18 e Å3
2695 reflectionsΔρmin = 0.15 e Å3
225 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
O310.69503 (12)0.31070 (7)0.07462 (5)0.0428 (3)
O110.44066 (13)0.60432 (9)0.13920 (7)0.0622 (4)
O120.40951 (11)0.43148 (8)0.09764 (6)0.0472 (3)
O510.85983 (16)0.25801 (10)0.30537 (6)0.0627 (4)
O520.98000 (17)0.22265 (10)0.19299 (6)0.0688 (4)
O611.08487 (11)0.46033 (8)0.13149 (5)0.0455 (3)
O621.01275 (11)0.35650 (8)0.02589 (5)0.0431 (3)
C110.50345 (15)0.51775 (10)0.11240 (7)0.0350 (4)
C210.69856 (15)0.51305 (10)0.09419 (7)0.0347 (3)
C310.78566 (15)0.39947 (10)0.11505 (7)0.0332 (3)
C410.78738 (17)0.38158 (11)0.20312 (7)0.0398 (4)
C510.88543 (17)0.27801 (11)0.23168 (8)0.0427 (4)
C610.97426 (15)0.40111 (10)0.08600 (7)0.0346 (3)
N10.82320 (16)0.18706 (10)0.05817 (7)0.0497 (4)
C20.8459 (2)0.22022 (14)0.13027 (9)0.0562 (5)
C30.8327 (2)0.14309 (16)0.19125 (9)0.0625 (6)
C40.7987 (2)0.03385 (16)0.17563 (9)0.0628 (6)
C50.7391 (2)0.11459 (14)0.07793 (11)0.0498 (5)
C60.7164 (2)0.14220 (15)0.00272 (12)0.0689 (6)
C70.7289 (2)0.06036 (14)0.05581 (11)0.0655 (6)
C80.7652 (2)0.04851 (13)0.03880 (9)0.0572 (5)
C90.78666 (18)0.07852 (11)0.03881 (8)0.0443 (4)
C100.77402 (18)0.00213 (13)0.09901 (9)0.0646 (6)
H510.931 (3)0.203 (2)0.3252 (13)0.080 (8)*
H21A0.763800.573100.123600.0420*
H21B0.709100.527700.037800.0420*
H310.586 (3)0.3302 (15)0.0746 (10)0.064 (5)*
H41A0.842800.447800.229400.0480*
H41B0.662800.376900.218700.0480*
H611.208 (3)0.4490 (17)0.1150 (12)0.088 (6)*
H10.832 (3)0.2372 (17)0.0209 (12)0.074 (6)*
H20.871200.296700.140600.0680*
H30.847300.166700.243400.0750*
H40.791500.019000.217100.0750*
H50.731500.171100.117000.0780*
H60.691800.217700.010500.0830*
H70.711700.081100.108300.0790*
H80.775800.103200.079100.0690*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O310.0297 (5)0.0399 (5)0.0592 (6)0.0029 (4)0.0066 (4)0.0124 (4)
O110.0347 (5)0.0547 (6)0.0974 (8)0.0032 (5)0.0045 (5)0.0326 (6)
O120.0253 (5)0.0451 (5)0.0711 (6)0.0022 (4)0.0030 (4)0.0105 (4)
O510.0738 (7)0.0627 (7)0.0537 (6)0.0255 (6)0.0220 (5)0.0206 (5)
O520.0789 (8)0.0706 (7)0.0585 (6)0.0392 (6)0.0184 (6)0.0070 (5)
O610.0257 (5)0.0609 (6)0.0498 (5)0.0017 (4)0.0023 (4)0.0123 (4)
O620.0353 (5)0.0516 (6)0.0434 (5)0.0009 (4)0.0107 (4)0.0081 (4)
C110.0282 (6)0.0404 (7)0.0360 (6)0.0017 (5)0.0021 (5)0.0018 (5)
C210.0284 (6)0.0361 (6)0.0396 (6)0.0019 (5)0.0014 (5)0.0006 (5)
C310.0260 (6)0.0348 (6)0.0389 (6)0.0006 (5)0.0036 (5)0.0034 (5)
C410.0353 (7)0.0429 (7)0.0419 (7)0.0068 (5)0.0097 (5)0.0026 (5)
C510.0393 (7)0.0436 (7)0.0459 (7)0.0043 (6)0.0079 (5)0.0036 (6)
C610.0278 (6)0.0377 (6)0.0385 (6)0.0021 (5)0.0027 (5)0.0005 (5)
N10.0546 (7)0.0443 (7)0.0497 (7)0.0104 (5)0.0025 (5)0.0084 (6)
C20.0492 (9)0.0582 (9)0.0615 (9)0.0132 (7)0.0050 (7)0.0075 (7)
C30.0566 (10)0.0827 (12)0.0487 (8)0.0153 (8)0.0072 (7)0.0000 (8)
C40.0558 (9)0.0776 (12)0.0550 (9)0.0078 (8)0.0032 (7)0.0235 (8)
C50.0378 (7)0.0543 (9)0.0575 (8)0.0062 (6)0.0034 (6)0.0165 (7)
C60.0579 (10)0.0494 (9)0.1007 (14)0.0040 (7)0.0172 (9)0.0010 (9)
C70.0676 (11)0.0598 (10)0.0701 (10)0.0139 (8)0.0130 (8)0.0081 (8)
C80.0667 (10)0.0535 (9)0.0513 (8)0.0139 (7)0.0023 (7)0.0055 (7)
C90.0384 (7)0.0441 (8)0.0502 (8)0.0100 (6)0.0003 (6)0.0074 (6)
C100.0538 (9)0.0512 (9)0.0894 (13)0.0006 (7)0.0090 (8)0.0255 (8)
Geometric parameters (Å, º) top
O31—C311.4188 (15)C21—H21A0.9900
O11—C111.2347 (16)C41—H41B0.9900
O12—C111.2656 (15)C41—H41A0.9900
O31—H310.85 (2)C2—C31.392 (2)
O51—C511.3108 (17)C3—C41.357 (3)
O52—C511.1979 (18)C4—C101.404 (2)
O51—H510.90 (2)C5—C101.418 (2)
O61—C611.3140 (15)C5—C61.351 (3)
O62—C611.2095 (15)C6—C71.399 (3)
O61—H610.99 (2)C7—C81.362 (2)
N1—C91.3681 (18)C8—C91.396 (2)
N1—C21.318 (2)C9—C101.410 (2)
N1—H10.88 (2)C2—H20.9500
C11—C211.5182 (16)C3—H30.9500
C21—C311.5381 (17)C4—H40.9500
C31—C411.5246 (17)C5—H50.9500
C31—C611.5295 (16)C6—H60.9500
C41—C511.5063 (18)C7—H70.9500
C21—H21B0.9900C8—H80.9500
C31—O31—H31103.4 (12)C51—C41—H41A109.00
C51—O51—H51112.3 (14)C51—C41—H41B109.00
C61—O61—H61109.1 (12)H41A—C41—H41B108.00
C2—N1—C9123.35 (13)N1—C2—C3119.92 (15)
C9—N1—H1118.5 (13)C2—C3—C4119.50 (15)
C2—N1—H1118.1 (13)C3—C4—C10120.94 (15)
O11—C11—O12122.24 (11)C6—C5—C10120.61 (16)
O11—C11—C21120.11 (11)C5—C6—C7120.51 (16)
O12—C11—C21117.64 (10)C6—C7—C8121.17 (17)
C11—C21—C31112.87 (10)C7—C8—C9118.94 (15)
C41—C31—C61111.59 (10)N1—C9—C10118.29 (13)
O31—C31—C41110.90 (10)C8—C9—C10121.08 (13)
O31—C31—C21110.91 (9)N1—C9—C8120.62 (13)
O31—C31—C61106.21 (9)C5—C10—C9117.68 (14)
C21—C31—C41109.48 (10)C4—C10—C5124.32 (15)
C21—C31—C61107.67 (9)C4—C10—C9118.00 (14)
C31—C41—C51114.43 (11)N1—C2—H2120.00
O51—C51—C41111.53 (11)C3—C2—H2120.00
O51—C51—O52123.89 (13)C2—C3—H3120.00
O52—C51—C41124.54 (13)C4—C3—H3120.00
O61—C61—C31112.41 (10)C3—C4—H4120.00
O61—C61—O62124.66 (11)C10—C4—H4120.00
O62—C61—C31122.86 (11)C6—C5—H5120.00
C11—C21—H21A109.00C10—C5—H5120.00
C11—C21—H21B109.00C5—C6—H6120.00
H21A—C21—H21B108.00C7—C6—H6120.00
C31—C21—H21A109.00C6—C7—H7119.00
C31—C21—H21B109.00C8—C7—H7119.00
C31—C41—H41A109.00C7—C8—H8121.00
C31—C41—H41B109.00C9—C8—H8121.00
C2—N1—C9—C100.5 (2)C31—C41—C51—O5211.94 (19)
C9—N1—C2—C30.1 (2)C31—C41—C51—O51170.43 (11)
C2—N1—C9—C8179.57 (14)N1—C2—C3—C40.8 (2)
O12—C11—C21—C3140.13 (15)C2—C3—C4—C101.0 (2)
O11—C11—C21—C31141.26 (12)C3—C4—C10—C90.4 (2)
C11—C21—C31—C4164.53 (13)C3—C4—C10—C5179.63 (15)
C11—C21—C31—C61173.98 (10)C6—C5—C10—C90.9 (2)
C11—C21—C31—O3158.17 (13)C10—C5—C6—C70.7 (2)
O31—C31—C41—C5162.88 (13)C6—C5—C10—C4179.79 (15)
O31—C31—C61—O61164.52 (10)C5—C6—C7—C80.4 (2)
C21—C31—C61—O6176.61 (12)C6—C7—C8—C91.3 (2)
C21—C31—C61—O62100.34 (13)C7—C8—C9—C101.0 (2)
C41—C31—C61—O6143.55 (14)C7—C8—C9—N1180.00 (14)
C21—C31—C41—C51174.41 (10)N1—C9—C10—C40.4 (2)
C61—C31—C41—C5155.31 (14)N1—C9—C10—C5178.95 (13)
C41—C31—C61—O62139.50 (12)C8—C9—C10—C4179.42 (14)
O31—C31—C61—O6218.52 (15)C8—C9—C10—C50.10 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O310.88 (2)2.17 (2)2.9215 (15)144 (2)
N1—H1···O620.88 (2)2.10 (2)2.8219 (15)140 (2)
O51—H51···O11i0.90 (2)1.62 (2)2.5208 (16)180 (3)
O31—H31···O120.85 (2)1.85 (2)2.6337 (13)151.4 (17)
O61—H61···O11ii0.99 (2)2.57 (2)3.1758 (14)119.6 (14)
O61—H61···O12ii0.99 (2)1.58 (2)2.5641 (12)174 (2)
C7—H7···O51i0.952.503.314 (2)144
C8—H8···O310.952.553.2358 (18)129
C21—H21B···O12iii0.992.493.4087 (16)154
Symmetry codes: (i) x+3/2, y1/2, z+1/2; (ii) x+1, y, z; (iii) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC9H8N+·C6H7O7
Mr321.28
Crystal system, space groupMonoclinic, P21/n
Temperature (K)130
a, b, c (Å)7.5202 (6), 11.9267 (10), 17.1484 (14)
β (°) 93.217 (1)
V3)1535.6 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.50 × 0.35 × 0.30
Data collection
DiffractometerBruker SMART CCD detector
Absorption correctionMulti-scan
(SADABS; Bruker, 1999)
Tmin, Tmax0.95, 0.97
No. of measured, independent and
observed [I > 2σ(I)] reflections
7847, 2695, 2431
Rint0.020
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.092, 1.07
No. of reflections2695
No. of parameters225
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.18, 0.15

Computer programs: SMART (Bruker, 2000), SMART, SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), PLATON.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O310.88 (2)2.17 (2)2.9215 (15)144 (2)
N1—H1···O620.88 (2)2.10 (2)2.8219 (15)140 (2)
O51—H51···O11i0.90 (2)1.62 (2)2.5208 (16)180 (3)
O31—H31···O120.85 (2)1.85 (2)2.6337 (13)151.4 (17)
O61—H61···O11ii0.99 (2)2.57 (2)3.1758 (14)119.6 (14)
O61—H61···O12ii0.99 (2)1.58 (2)2.5641 (12)174 (2)
Symmetry codes: (i) x+3/2, y1/2, z+1/2; (ii) x+1, y, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds