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In the title compound, C11H10N+·C4H5O6·2H2O, hydrogen tartrate anions and water mol­ecules are linked by strong O—H...O hydrogen bonds to form corrugated layers. The 4-phenyl­pyridinium cation decorates the layer from both sides, being hydrogen bonded to the water mol­ecule only. The three-dimensional packing of the complex layers is accomplished by strong π–π inter­actions of 3.668 (2) Å between the centroids of the benzyl and pyridine rings related by the symmetry operator (x − {1 \over 2}, −y + {1 \over 2}, −z).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807017217/hb2365sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807017217/hb2365Isup2.hkl
Contains datablock I

CCDC reference: 647600

Key indicators

  • Single-crystal X-ray study
  • T = 290 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.045
  • wR factor = 0.119
  • Data-to-parameter ratio = 10.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.85 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT417_ALERT_2_C Short Inter D-H..H-D HW2B .. H21N .. 2.13 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 6
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.97 From the CIF: _reflns_number_total 2180 Count of symmetry unique reflns 2178 Completeness (_total/calc) 100.09% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2 Fraction of Friedel pairs measured 0.001 Are heavy atom types Z>Si present no PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The synthesis and structure determination of the title compound, (I) [systematic name: 4-phenylpyridinium 3-carboxy-2,3-dihydroxypropanoate dihydrate], were carried out as a part of our project dealing with organic compounds with potential nonlinear-optical, photorefractive and electro-optical properties (Kolev et al., 2005, 2004, 1997).

Compound (I) is attractive from a crystal engineering and supramolecular chemistry point of view because it posseses a non-centrosymmetric structure and large dipole moments (Zyss et al., 1993). Recent theoretical calculations for torsional barriers and nonlinear-optical properties of phenylpyridines (Alyar et al., 2006) revealed that such molecules posses very weak nonlinear optical properties. However, the second-harmonic generation (SHG) of crystalline materials depends on both the magnitude of the molecular hyperpolarizability and the orientation of the molecules in the crystal lattice. Owing to its ability to form multidirectional hydrogen bonds, L-tartaric acid builds acentric crystalline salts with many organic bases (Turkington et al., 2005; Farrell et al., 2002; Guru Row, 1999; Akeroy & Hitchcock, 1993). Moreover, a number of salts of L-tartaric acid and substituted pyridines have been prepared and quantitative measurements showed that those materials are SHG active (Dastidar et al., 1993).

Crystallization from H2O–methanol solutions of an equimolar mixture of 4-phenylpyridine (H4PPN) and L-tartaric acid gives the title compound, (I), in which complete transfer of a single H atom from the acid component to the basic component has occurred. The geometric parameters of both organic molecules are comparable with those reported earlier (Kolev et al., 2004, 2005; Zyss et al., 1993; Turkington et al., 2005). The 4PPN+ cation exhibits an interplanar angle of 34.15 (1)°, comparable with ones found previously in 4PPN-hydrogensquarate and 4PPN-betaine of squaric acid [31.6 (1)° and 28.6 (1)°, respectively].

An extensive hydrogen-bonding network is observed in the structure of (I) (Table 1). The hydrogentartrate (HT) anions are linked by strong bifurcated O41—H41···.(O11, O12) hydrogen bonds to form chains with graph-set symbol C(7)/R21(4) along the a axis. There are two water molecules of crystallization in the structure and both act as bridges between neighbouring HT chains through hydrogen bonding. Each of the water solvent molecules holds three symmetry-related HT molecules to form undulating layers infinite in the a and b directions and stacked along the c direction. The 4PPN cation decorates both sides of the layers taking part in the formation of N21—H21···OW2 hydrogen bond.

The same crystal packing was found for L-tartaric acid 4-dimethilaminopyridine dihydrate, (II) (Dastidar et al., 1993). In (I), similar to the 4-dimethylaminopyridinium cation in (II), the 4PPN anions are superimposed with dipoles in opposite orientations to each other, and consequently no resultant second-order susceptibility Ξ2 could be expected. The only difference is that the cation in (II) is hydrogen-bonded to an HT anion and not to a water molecule as in (I). Nevertheless, both structures crystallize in the orthorhombic P212121 space group with close values for a and b cell parameters [7.305 (2) and 11.850 (2) Å in (I), and 7.321 (1) and 11.846 (1) Å in (II)]. Only the stacking parameter c in (I) is longer, due to the larger cation used [18.165 (3) Å in (I) versus 16.469 (1) Å in (II)]. Taking into consideration the measurements and conclusions made by Dastidar et al., it could be expected that (I) will show similar values for the nonlinear response parameters as (II). It is possible that strong ππ interactions between neighbouring 4PPN anions will improve the SHG activity of (I) [Cg1···Cg2i = 3.668 (2) Å; symmetry code: (i) x - 1/2, -y + 1/2, -z; Cg1 and Cg2 are the centroids of the 4PPN benzyl and pyridine rings, respectively].

Related literature top

For related literature, see: Akeroy & Hitchcock (1993); Alyar et al. (2006); Dastidar et al. (1993); Farrell et al. (2002); Guru Row (1999); Kolev et al. (1997, 2004, 2005); Turkington et al. (2005); Zyss et al. (1993).

Experimental top

Equimolecular amounts of 4-phenylpyridine (2.15 mmol, 334 mg) and tartaric acid (324 mg) were mixed in distilled water (20 ml). The reaction mixture was stirred for 6 h at room temperature and monitored by thin-layer chromatography.

After completion of the reaction, the obtained solution was filtered and the filtrate set aside. The deposition of crystals of (I) began after one week. The product was separated by filtration and dried in air.

Refinement top

The water H atoms were located in a difference map. The other H atoms were placed in idealized positions, with O—H = 0.82 Å, C—H = 0.93 Å and N—H = 0.86 Å. All H atoms were refined as riding, with Uiso(H) = 1.2Ueq(C or N) or 1.5Ueq(O).

Structure description top

The synthesis and structure determination of the title compound, (I) [systematic name: 4-phenylpyridinium 3-carboxy-2,3-dihydroxypropanoate dihydrate], were carried out as a part of our project dealing with organic compounds with potential nonlinear-optical, photorefractive and electro-optical properties (Kolev et al., 2005, 2004, 1997).

Compound (I) is attractive from a crystal engineering and supramolecular chemistry point of view because it posseses a non-centrosymmetric structure and large dipole moments (Zyss et al., 1993). Recent theoretical calculations for torsional barriers and nonlinear-optical properties of phenylpyridines (Alyar et al., 2006) revealed that such molecules posses very weak nonlinear optical properties. However, the second-harmonic generation (SHG) of crystalline materials depends on both the magnitude of the molecular hyperpolarizability and the orientation of the molecules in the crystal lattice. Owing to its ability to form multidirectional hydrogen bonds, L-tartaric acid builds acentric crystalline salts with many organic bases (Turkington et al., 2005; Farrell et al., 2002; Guru Row, 1999; Akeroy & Hitchcock, 1993). Moreover, a number of salts of L-tartaric acid and substituted pyridines have been prepared and quantitative measurements showed that those materials are SHG active (Dastidar et al., 1993).

Crystallization from H2O–methanol solutions of an equimolar mixture of 4-phenylpyridine (H4PPN) and L-tartaric acid gives the title compound, (I), in which complete transfer of a single H atom from the acid component to the basic component has occurred. The geometric parameters of both organic molecules are comparable with those reported earlier (Kolev et al., 2004, 2005; Zyss et al., 1993; Turkington et al., 2005). The 4PPN+ cation exhibits an interplanar angle of 34.15 (1)°, comparable with ones found previously in 4PPN-hydrogensquarate and 4PPN-betaine of squaric acid [31.6 (1)° and 28.6 (1)°, respectively].

An extensive hydrogen-bonding network is observed in the structure of (I) (Table 1). The hydrogentartrate (HT) anions are linked by strong bifurcated O41—H41···.(O11, O12) hydrogen bonds to form chains with graph-set symbol C(7)/R21(4) along the a axis. There are two water molecules of crystallization in the structure and both act as bridges between neighbouring HT chains through hydrogen bonding. Each of the water solvent molecules holds three symmetry-related HT molecules to form undulating layers infinite in the a and b directions and stacked along the c direction. The 4PPN cation decorates both sides of the layers taking part in the formation of N21—H21···OW2 hydrogen bond.

The same crystal packing was found for L-tartaric acid 4-dimethilaminopyridine dihydrate, (II) (Dastidar et al., 1993). In (I), similar to the 4-dimethylaminopyridinium cation in (II), the 4PPN anions are superimposed with dipoles in opposite orientations to each other, and consequently no resultant second-order susceptibility Ξ2 could be expected. The only difference is that the cation in (II) is hydrogen-bonded to an HT anion and not to a water molecule as in (I). Nevertheless, both structures crystallize in the orthorhombic P212121 space group with close values for a and b cell parameters [7.305 (2) and 11.850 (2) Å in (I), and 7.321 (1) and 11.846 (1) Å in (II)]. Only the stacking parameter c in (I) is longer, due to the larger cation used [18.165 (3) Å in (I) versus 16.469 (1) Å in (II)]. Taking into consideration the measurements and conclusions made by Dastidar et al., it could be expected that (I) will show similar values for the nonlinear response parameters as (II). It is possible that strong ππ interactions between neighbouring 4PPN anions will improve the SHG activity of (I) [Cg1···Cg2i = 3.668 (2) Å; symmetry code: (i) x - 1/2, -y + 1/2, -z; Cg1 and Cg2 are the centroids of the 4PPN benzyl and pyridine rings, respectively].

For related literature, see: Akeroy & Hitchcock (1993); Alyar et al. (2006); Dastidar et al. (1993); Farrell et al. (2002); Guru Row (1999); Kolev et al. (1997, 2004, 2005); Turkington et al. (2005); Zyss et al. (1993).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of (I), showing 50% probability displacement ellipsoids. H atoms are shown as spheres of arbitrary radii.
[Figure 2] Fig. 2. A view of the molecular packing in (I). Hydrogen bonds are represented by dotted lines. All H atoms except those involved in hydrogen-bond interactions have been omitted. [Symmetry codes: (i) -x + 1, y - 1/2, -z + 3/2; (ii) -x + 1, y + 1/2, -z + 3/2.]
4-Phenylpyridinium 3-carboxy-2,3-dihydroxypropanoate dihydrate top
Crystal data top
C11H10N+·C4H5O6·2H2OF(000) = 720
Mr = 341.31Dx = 1.442 Mg m3
Dm = not meaured Mg m3
Dm measured by none
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 22 reflections
a = 7.3051 (16) Åθ = 18.1–19.5°
b = 11.850 (2) ŵ = 0.12 mm1
c = 18.165 (3) ÅT = 290 K
V = 1572.5 (5) Å3Prism, brown
Z = 40.20 × 0.13 × 0.13 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.048
Radiation source: fine-focus sealed tubeθmax = 28.0°, θmin = 2.1°
Graphite monochromatorh = 09
nonprofiled ω/2θ scansk = 015
4241 measured reflectionsl = 2323
2180 independent reflections3 standard reflections every 120 min
1406 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H-atom parameters constrained
S = 0.94 w = 1/[σ2(Fo2) + (0.0534P)2 + 0.3826P]
where P = (Fo2 + 2Fc2)/3
2180 reflections(Δ/σ)max < 0.001
217 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.20 e Å3
Crystal data top
C11H10N+·C4H5O6·2H2OV = 1572.5 (5) Å3
Mr = 341.31Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.3051 (16) ŵ = 0.12 mm1
b = 11.850 (2) ÅT = 290 K
c = 18.165 (3) Å0.20 × 0.13 × 0.13 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.048
4241 measured reflections3 standard reflections every 120 min
2180 independent reflections intensity decay: none
1406 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.119H-atom parameters constrained
S = 0.94Δρmax = 0.18 e Å3
2180 reflectionsΔρmin = 0.20 e Å3
217 parameters
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
C10.0051 (4)0.2771 (3)0.86282 (19)0.0299 (7)
C20.2041 (4)0.2727 (3)0.86494 (19)0.0316 (7)
H20.24120.22120.90440.038*
C30.2900 (4)0.3865 (3)0.87922 (19)0.0321 (8)
H30.26110.40940.92970.039*
C40.4989 (4)0.3800 (3)0.8712 (2)0.0314 (8)
C2120.4524 (5)0.1070 (3)0.4994 (2)0.0425 (9)
H2120.47970.09370.54870.051*
C2110.4563 (6)0.0194 (3)0.4502 (2)0.0475 (10)
H2110.49010.05230.46580.057*
C2100.4095 (6)0.0378 (4)0.3768 (2)0.0513 (10)
H2100.40930.02180.34350.062*
C290.3640 (6)0.1439 (3)0.3542 (2)0.0495 (11)
H290.33320.15610.30520.059*
C280.3629 (5)0.2332 (3)0.4027 (2)0.0422 (9)
H280.33210.30520.38640.051*
C270.4084 (5)0.2152 (3)0.47646 (18)0.0372 (8)
C240.4095 (5)0.3097 (3)0.52912 (18)0.0361 (8)
C230.4631 (5)0.4188 (3)0.5084 (2)0.0415 (9)
H230.50000.43270.46030.050*
C220.4616 (5)0.5052 (3)0.5587 (2)0.0469 (10)
H220.49570.57770.54470.056*
C260.3556 (6)0.3821 (4)0.6505 (2)0.0497 (10)
H260.31790.37160.69890.060*
C250.3547 (5)0.2934 (4)0.6024 (2)0.0453 (10)
H250.31780.22230.61820.054*
N210.4108 (5)0.4841 (3)0.62782 (18)0.0476 (8)
H21N0.41370.53840.65920.057*
O110.0810 (3)0.2321 (2)0.81114 (14)0.0473 (7)
O120.0837 (3)0.3244 (2)0.91785 (12)0.0418 (6)
O210.2725 (3)0.2304 (2)0.79728 (14)0.0447 (7)
H210.19360.19190.77730.067*
O310.2197 (3)0.4688 (2)0.83042 (15)0.0454 (7)
H310.26900.52970.83860.068*
O410.5784 (3)0.3136 (2)0.91606 (13)0.0426 (6)
H410.68890.31380.90800.064*
O420.5708 (3)0.4383 (2)0.82451 (16)0.0525 (7)
OW10.1312 (4)0.0776 (2)0.69310 (15)0.0504 (7)
HW1A0.21120.01760.68740.060*
HW1B0.05270.02750.70420.060*
OW20.3906 (3)0.63832 (19)0.73677 (14)0.0460 (7)
HW2A0.47420.68290.73000.055*
HW2B0.31840.67620.72450.055*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0153 (14)0.0318 (17)0.0427 (19)0.0011 (13)0.0001 (13)0.0067 (16)
C20.0168 (14)0.0358 (18)0.0424 (19)0.0002 (14)0.0010 (14)0.0014 (16)
C30.0159 (15)0.0396 (18)0.0408 (18)0.0001 (14)0.0007 (14)0.0035 (17)
C40.0161 (14)0.0349 (18)0.0433 (19)0.0030 (14)0.0006 (14)0.0080 (17)
C2120.041 (2)0.0417 (19)0.045 (2)0.0032 (17)0.0082 (17)0.0096 (17)
C2110.045 (2)0.041 (2)0.057 (2)0.0001 (19)0.0054 (19)0.0081 (19)
C2100.052 (2)0.052 (2)0.050 (2)0.007 (2)0.002 (2)0.0044 (19)
C290.056 (3)0.055 (2)0.038 (2)0.001 (2)0.0018 (19)0.0077 (19)
C280.039 (2)0.044 (2)0.044 (2)0.0032 (18)0.0016 (16)0.0094 (18)
C270.0274 (17)0.0424 (19)0.0417 (19)0.0042 (17)0.0001 (16)0.0105 (16)
C240.0255 (17)0.0429 (19)0.0398 (18)0.0030 (17)0.0019 (17)0.0047 (16)
C230.034 (2)0.048 (2)0.042 (2)0.0019 (17)0.0020 (16)0.0096 (18)
C220.036 (2)0.048 (2)0.056 (2)0.0040 (19)0.0011 (18)0.004 (2)
C260.044 (2)0.061 (3)0.044 (2)0.001 (2)0.0032 (18)0.004 (2)
C250.041 (2)0.050 (2)0.045 (2)0.0041 (18)0.0029 (17)0.0106 (19)
N210.0381 (17)0.0514 (19)0.053 (2)0.0016 (17)0.0016 (17)0.0049 (16)
O110.0208 (12)0.0649 (17)0.0562 (15)0.0020 (13)0.0027 (12)0.0196 (14)
O120.0170 (12)0.0671 (17)0.0412 (13)0.0001 (12)0.0002 (11)0.0073 (13)
O210.0234 (12)0.0513 (15)0.0594 (15)0.0046 (12)0.0067 (12)0.0217 (14)
O310.0244 (13)0.0331 (13)0.0786 (19)0.0017 (11)0.0014 (13)0.0088 (13)
O410.0146 (11)0.0641 (16)0.0491 (14)0.0010 (12)0.0007 (11)0.0057 (13)
O420.0233 (13)0.0605 (17)0.0738 (19)0.0047 (13)0.0049 (13)0.0210 (15)
OW10.0327 (14)0.0416 (14)0.0770 (18)0.0004 (12)0.0008 (13)0.0104 (14)
OW20.0281 (12)0.0384 (13)0.0716 (17)0.0010 (11)0.0035 (13)0.0132 (12)
Geometric parameters (Å, º) top
C1—O111.213 (4)C28—H280.9300
C1—O121.282 (4)C27—C241.473 (5)
C1—C21.530 (4)C24—C231.402 (5)
C2—O211.419 (4)C24—C251.403 (5)
C2—C31.510 (5)C23—C221.372 (5)
C2—H20.9800C23—H230.9300
C3—O311.415 (4)C22—N211.333 (5)
C3—C41.535 (4)C22—H220.9300
C3—H30.9800C26—N211.339 (5)
C4—O421.213 (4)C26—C251.367 (5)
C4—O411.273 (4)C26—H260.9300
C212—C2111.370 (6)C25—H250.9300
C212—C271.386 (5)N21—H21N0.8600
C212—H2120.9300O21—H210.8200
C211—C2101.394 (6)O31—H310.8200
C211—H2110.9300O41—H410.8200
C210—C291.363 (6)OW1—HW1A0.9258
C210—H2100.9300OW1—HW1B0.8495
C29—C281.377 (5)OW2—HW2A0.8170
C29—H290.9300OW2—HW2B0.7278
C28—C271.398 (5)
O11—C1—O12126.2 (3)C29—C28—C27119.6 (4)
O11—C1—C2117.4 (3)C29—C28—H28120.2
O12—C1—C2116.3 (3)C27—C28—H28120.2
O21—C2—C3108.6 (3)C212—C27—C28119.0 (4)
O21—C2—C1110.0 (3)C212—C27—C24120.5 (3)
C3—C2—C1112.9 (3)C28—C27—C24120.5 (3)
O21—C2—H2108.4C23—C24—C25117.5 (3)
C3—C2—H2108.4C23—C24—C27121.9 (3)
C1—C2—H2108.4C25—C24—C27120.6 (3)
O31—C3—C2110.9 (3)C22—C23—C24120.5 (3)
O31—C3—C4109.6 (3)C22—C23—H23119.7
C2—C3—C4110.6 (3)C24—C23—H23119.7
O31—C3—H3108.5N21—C22—C23119.3 (4)
C2—C3—H3108.5N21—C22—H22120.4
C4—C3—H3108.5C23—C22—H22120.4
O42—C4—O41127.0 (3)N21—C26—C25119.9 (4)
O42—C4—C3118.0 (3)N21—C26—H26120.1
O41—C4—C3115.0 (3)C25—C26—H26120.1
C211—C212—C27120.6 (3)C26—C25—C24120.0 (4)
C211—C212—H212119.7C26—C25—H25120.0
C27—C212—H212119.7C24—C25—H25120.0
C212—C211—C210120.1 (4)C22—N21—C26122.9 (4)
C212—C211—H211120.0C22—N21—H21N118.6
C210—C211—H211120.0C26—N21—H21N118.6
C29—C210—C211119.4 (4)C2—O21—H21109.5
C29—C210—H210120.3C3—O31—H31109.5
C211—C210—H210120.3C4—O41—H41109.5
C210—C29—C28121.3 (4)HW1A—OW1—HW1B85.2
C210—C29—H29119.4HW2A—OW2—HW2B95.5
C28—C29—H29119.4
C23—C22—N21—C261.9 (6)C29—C210—C211—C2121.5 (7)
N21—C22—C23—C240.9 (6)C210—C211—C212—C272.2 (6)
C22—C23—C24—C250.1 (5)C211—C212—C27—C24178.3 (3)
C22—C23—C24—C27179.6 (3)C211—C212—C27—C281.7 (6)
C23—C24—C25—C260.2 (5)O11—C1—C2—O219.5 (5)
C27—C24—C25—C26179.7 (4)O11—C1—C2—C3130.9 (3)
C23—C24—C27—C2834.9 (6)O12—C1—C2—O21173.3 (3)
C23—C24—C27—C212145.1 (4)O12—C1—C2—C351.8 (4)
C25—C24—C27—C28144.6 (4)O21—C2—C3—O3171.2 (3)
C25—C24—C27—C21235.4 (6)O21—C2—C3—C450.6 (4)
C24—C25—C26—N210.8 (6)C1—C2—C3—O3151.0 (4)
C25—C26—N21—C221.9 (6)C1—C2—C3—C4172.9 (3)
C24—C27—C28—C29179.5 (4)O31—C3—C4—O41175.6 (3)
C212—C27—C28—C290.5 (6)O31—C3—C4—O423.4 (5)
C27—C28—C29—C2100.3 (6)C2—C3—C4—O4161.8 (4)
C211—C210—C29—C280.2 (7)C2—C3—C4—O42119.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N21—H21N···OW20.861.852.698 (4)169
O21—H21···O110.822.152.595 (3)114
O21—H21···OW10.822.092.815 (3)147
O31—H31···OW20.822.422.913 (3)119
O41—H41···O12i0.821.682.472 (3)163
OW1—HW1B···O31ii0.852.202.901 (3)140
OW1—HW1A···O42iii0.931.862.750 (4)160
OW2—HW2A···O21iv0.822.002.762 (3)156
OW2—HW2B···O11v0.731.972.666 (3)161
Symmetry codes: (i) x+1, y, z; (ii) x, y1/2, z+3/2; (iii) x+1, y1/2, z+3/2; (iv) x+1, y+1/2, z+3/2; (v) x, y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC11H10N+·C4H5O6·2H2O
Mr341.31
Crystal system, space groupOrthorhombic, P212121
Temperature (K)290
a, b, c (Å)7.3051 (16), 11.850 (2), 18.165 (3)
V3)1572.5 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.12
Crystal size (mm)0.20 × 0.13 × 0.13
Data collection
DiffractometerEnraf–Nonius CAD-4
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
4241, 2180, 1406
Rint0.048
(sin θ/λ)max1)0.660
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.119, 0.94
No. of reflections2180
No. of parameters217
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.18, 0.20

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), CAD-4 EXPRESS, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N21—H21N···OW20.861.852.698 (4)169
O21—H21···O110.822.152.595 (3)114
O21—H21···OW10.822.092.815 (3)147
O31—H31···OW20.822.422.913 (3)119
O41—H41···O12i0.821.682.472 (3)163
OW1—HW1B···O31ii0.852.202.901 (3)140
OW1—HW1A···O42iii0.931.862.750 (4)160
OW2—HW2A···O21iv0.822.002.762 (3)156
OW2—HW2B···O11v0.731.972.666 (3)161
Symmetry codes: (i) x+1, y, z; (ii) x, y1/2, z+3/2; (iii) x+1, y1/2, z+3/2; (iv) x+1, y+1/2, z+3/2; (v) x, y+1/2, z+3/2.
 

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