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ISSN: 2056-9890

Adipic acid–2,6-bis­­(1H-benzimidazol-2-yl)pyridine–water (1/2/4)

aNortheast Dianli University, Jilin 132012, People's Republic of China
*Correspondence e-mail: songzhulin@hotmail.com

(Received 19 October 2012; accepted 21 November 2012; online 28 November 2012)

The asymmetric unit of the title hydrated co-crystal, 2C19H13N5·C6H10O4·4H2O, consists of one 2,6-bis­(1H-benzimidazol-2-yl)pyridine mol­ecule, half of an adipic acid mol­ecule (bis­ected by an inversion center) and two water solvates. In the crystal, N—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds and ππ inter­actions [centroid–centroid distances = 3.769 (2) and 3.731 (2) Å] form a three-dimensional supra­molecular structure.

Related literature

For related structures, see: Boča et al. (2000[Boča, M., Valigura, D., Svoboda, I., Fuess, H. & Linert, W. (2000). Acta Cryst. C56, 838-839.]); Chetia & Iyer (2006[Chetia, B. & Iyer, P. K. (2006). Tetrahedron Lett. 47, 8115-8117.], 2007[Chetia, B. & Iyer, P. K. (2007). Tetrahedron Lett. 48, 47-50.]); Xiao et al. (2010[Xiao, H., Wang, G. & Jian, F. (2010). Acta Cryst. C66, o446-o448.]); Freire et al. (2003[Freire, E., Baggio, S., Muñoz, J. C. & Baggio, R. (2003). Acta Cryst. C59, o259-o262.]); Lin et al. (2012[Lin, S., Jia, R. & He, A. (2012). Acta Cryst. E68, o1820.]).

[Scheme 1]

Experimental

Crystal data
  • 2C19H13N5·C6H10O4·4H2O

  • Mr = 840.90

  • Triclinic, [P \overline 1]

  • a = 9.0709 (18) Å

  • b = 9.6882 (19) Å

  • c = 12.311 (3) Å

  • α = 88.93 (3)°

  • β = 83.12 (3)°

  • γ = 75.14 (3)°

  • V = 1038.1 (4) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 295 K

  • 0.25 × 0.18 × 0.16 mm

Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • 10214 measured reflections

  • 4705 independent reflections

  • 3555 reflections with I > 2σ(I)

  • Rint = 0.024

  • 3 standard reflections every 100 reflections intensity decay: none

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.163

  • S = 1.15

  • 4705 reflections

  • 368 parameters

  • 7 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.36 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H4⋯O2W 0.95 (2) 2.16 (2) 3.084 (2) 163.3 (18)
N4—H5⋯O2W 0.88 (2) 2.08 (2) 2.945 (2) 167.6 (18)
O1—H1⋯N5 0.87 (1) 1.83 (1) 2.6731 (19) 163 (2)
O1W—H1WA⋯N1i 0.85 (1) 1.99 (1) 2.8169 (18) 162 (2)
O1W—H1WB⋯O2ii 0.85 (1) 1.99 (1) 2.815 (2) 165 (2)
O2W—H2WB⋯O1Wiii 0.86 (1) 2.05 (1) 2.898 (2) 170 (3)
O2W—H2WA⋯O1Wiv 0.87 (1) 2.01 (1) 2.867 (2) 171 (3)
Symmetry codes: (i) x, y, z+1; (ii) -x+1, -y, -z+1; (iii) -x, -y+1, -z+1; (iv) x, y+1, z-1.

Data collection: CAD-4 Software (Enraf–Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989[Gabe, E. J., Le Page, Y., Charland, J.-P., Lee, F. L. & White, P. S. (1989). J. Appl. Cryst. 22, 384-387.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: WinGX (Farrugia, 2012)[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.].

Supporting information


Comment top

Structures containing 2,6-bis(benzimidazol-2-yl)pyridine have been reported in recent year (Xiao et al., 2010; Freire et al., 2003; Lin et al., 2012). As a continuation of our previous works devoted to structures with 2,6-bis(benzimidazol-2-yl)pyridine, here we report the crystal structures of the title compound (C19H13N5)0.5(C6H10O4)2(H2O)(I). Its asymmetric unit consists of one 2-pyridin-4-yl-1H-benzoimidazole molecule, half of an adipic acid molecule (bisected by an inversion center) and two water solvates. The aromatic C—C and C—N distances in both the benzimidazole and pyridine rings are within the usual range. All C and N atoms of the 2,6-bis(benzimidazol-2-yl)pyridine molecule lay in a plane (largest deviation: 0.084 Å for C16). The compound is similar to other related compounds consisting of 2,6-bis(benzimidazol-2-yl)pyridine and organic molecules (Boča et al., 2000; Chetia and Iyer, 2006; Chetia and Iyer, 2007; Xiao et al., 2010; Lin et al., 2012).

The crystal structure in (I) is a 3D array, definend by N—H···O, O—H···O, O—H···N inter- and intramolecular interactions (Table 1) and ππ stacking interactions between rings with center-to-center distances Cg1···Cg2 = 3.769 (2) (symmetry code 1 - x, 1 - y, -z), Cg2···Cg3=3.731 (2) Å (symmetry code -x, 1 - y, -z), where Cg1, Cg2 and Cg3 refer to imidazole ring N4—C13—N5—C14—C19, pyridine ring N3—C8—C9—C10—C11—C12 and phenyl ring C1—C2—C3—C4—C5—C6, respectively.

Related literature top

For related structures, see: Boča et al. (2000); Chetia & Iyer (2006, 2007); Xiao et al. (2010); Freire et al. (2003); Lin et al. (2012).

Experimental top

The title compound was obtained by 2,6-bis(benzimidazol-2-yl)pyridine (0.062 g, 0.20 mmol) and adipic acid (0.029 g, 0.20 mmol) dissolved in 30 ml solution mixed with ethanol and water by 2:1(V/V) was heated to refluxed for 8 h and cooled to the room temperature. Single crystals suitable for X-ray measurements were obtained by recrystallization at room temperature.

Refinement top

The positions of all H atoms were found in a difference Fourier map, and refined both in coordinates as in displacement factors. Those attached to O were subject to distance restraints (O-H = 0.85 (1)Å).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top
[Figure 1] Fig. 1. The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.
Adipic acid–2,6-bis(1H-benzimidazol-2-yl)pyridine–water (1/2/4) top
Crystal data top
2C19H13N5·C6H10O4·4H2OZ = 1
Mr = 840.90F(000) = 442
Triclinic, P1Dx = 1.345 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.0709 (18) ÅCell parameters from 25 reflections
b = 9.6882 (19) Åθ = 4–14°
c = 12.311 (3) ŵ = 0.10 mm1
α = 88.93 (3)°T = 295 K
β = 83.12 (3)°Block, yellow
γ = 75.14 (3)°0.25 × 0.18 × 0.16 mm
V = 1038.1 (4) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.024
Radiation source: fine-focus sealed tubeθmax = 27.5°, θmin = 3.0°
Graphite monochromatorh = 1111
ω scansk = 1212
10214 measured reflectionsl = 1515
4705 independent reflections3 standard reflections every 100 reflections
3555 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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163H atoms treated by a mixture of independent and constrained refinement
S = 1.15 w = 1/[σ2(Fo2) + (0.1P)2 + 0.0268P]
where P = (Fo2 + 2Fc2)/3
4705 reflections(Δ/σ)max < 0.001
368 parametersΔρmax = 0.36 e Å3
7 restraintsΔρmin = 0.19 e Å3
Crystal data top
2C19H13N5·C6H10O4·4H2Oγ = 75.14 (3)°
Mr = 840.90V = 1038.1 (4) Å3
Triclinic, P1Z = 1
a = 9.0709 (18) ÅMo Kα radiation
b = 9.6882 (19) ŵ = 0.10 mm1
c = 12.311 (3) ÅT = 295 K
α = 88.93 (3)°0.25 × 0.18 × 0.16 mm
β = 83.12 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.024
10214 measured reflections3 standard reflections every 100 reflections
4705 independent reflections intensity decay: none
3555 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0477 restraints
wR(F2) = 0.163H atoms treated by a mixture of independent and constrained refinement
S = 1.15Δρmax = 0.36 e Å3
4705 reflectionsΔρmin = 0.19 e Å3
368 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
N10.13159 (14)0.33800 (13)0.15941 (10)0.0488 (3)
N20.11534 (14)0.56273 (13)0.10937 (10)0.0469 (3)
H40.142 (2)0.632 (2)0.0672 (17)0.070 (5)*
N30.30720 (13)0.47411 (12)0.04908 (9)0.0425 (3)
N40.35862 (15)0.69020 (12)0.16663 (10)0.0461 (3)
H50.296 (2)0.718 (2)0.1169 (17)0.071 (6)*
N50.51881 (14)0.53946 (12)0.26517 (10)0.0467 (3)
C10.03749 (17)0.43165 (17)0.22421 (12)0.0502 (3)
C20.0392 (2)0.4018 (2)0.30889 (15)0.0660 (5)
H2B0.029 (3)0.302 (3)0.331 (2)0.108 (9)*
C30.1263 (2)0.5167 (3)0.36062 (17)0.0737 (5)
H3B0.177 (2)0.500 (2)0.4221 (17)0.075 (6)*
C40.1367 (2)0.6559 (3)0.32926 (17)0.0738 (6)
H4B0.203 (2)0.737 (2)0.3704 (18)0.083 (6)*
C50.0618 (2)0.6887 (2)0.24504 (16)0.0625 (4)
H5B0.071 (2)0.784 (2)0.2255 (17)0.072 (6)*
C60.02658 (16)0.57252 (17)0.19362 (12)0.0495 (4)
C70.17580 (15)0.42054 (14)0.09313 (11)0.0436 (3)
C80.28186 (15)0.37145 (14)0.01174 (11)0.0423 (3)
C90.35464 (18)0.22746 (15)0.00130 (13)0.0500 (4)
H9A0.3296 (19)0.1624 (19)0.0465 (15)0.053 (4)*
C100.45920 (19)0.18978 (15)0.07321 (13)0.0533 (4)
H10A0.517 (2)0.086 (2)0.0801 (15)0.064 (5)*
C110.48672 (19)0.29346 (15)0.13676 (13)0.0496 (4)
H11A0.553 (2)0.2771 (19)0.1892 (15)0.058 (5)*
C120.40660 (15)0.43502 (14)0.12290 (11)0.0423 (3)
C130.42912 (15)0.55179 (14)0.18674 (11)0.0424 (3)
C140.50736 (17)0.67897 (15)0.29760 (12)0.0461 (3)
C150.5824 (2)0.72962 (19)0.37449 (15)0.0590 (4)
H15A0.653 (3)0.659 (2)0.4172 (19)0.085 (6)*
C160.5557 (2)0.8759 (2)0.38559 (16)0.0678 (5)
H16A0.607 (2)0.915 (2)0.4359 (18)0.080 (6)*
C170.4553 (2)0.96933 (19)0.32354 (16)0.0686 (5)
H17A0.442 (2)1.074 (2)0.3320 (17)0.080 (6)*
C180.3784 (2)0.92146 (17)0.24903 (14)0.0588 (4)
H18A0.308 (2)0.984 (2)0.2049 (17)0.072 (6)*
C190.40766 (17)0.77399 (15)0.23620 (12)0.0465 (3)
O10.67965 (16)0.37143 (12)0.40769 (11)0.0688 (4)
H10.630 (2)0.411 (2)0.3538 (14)0.084 (7)*
O20.74254 (17)0.17221 (13)0.30895 (11)0.0732 (4)
C200.75243 (17)0.23700 (16)0.38907 (13)0.0491 (3)
C210.8489 (2)0.17588 (17)0.47764 (14)0.0538 (4)
H21A0.784 (3)0.179 (2)0.5432 (19)0.079 (6)*
H21B0.915 (2)0.250 (2)0.4912 (16)0.073 (6)*
C220.9496 (2)0.02613 (17)0.45481 (14)0.0543 (4)
H22A0.883 (2)0.040 (2)0.4464 (16)0.069 (5)*
H22B1.019 (2)0.022 (2)0.3830 (17)0.071 (5)*
O1W0.14244 (18)0.04491 (14)0.85092 (11)0.0742 (4)
O2W0.14234 (16)0.82851 (14)0.01294 (13)0.0751 (4)
H1WA0.153 (3)0.1282 (13)0.8350 (18)0.102 (8)*
H1WB0.172 (3)0.0080 (19)0.7943 (13)0.093 (8)*
H2WB0.064 (3)0.870 (3)0.058 (2)0.152 (13)*
H2WA0.151 (3)0.896 (2)0.0326 (18)0.126 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0533 (7)0.0439 (7)0.0461 (7)0.0062 (5)0.0072 (5)0.0025 (5)
N20.0474 (6)0.0400 (6)0.0505 (7)0.0060 (5)0.0065 (5)0.0026 (5)
N30.0460 (6)0.0359 (5)0.0420 (6)0.0054 (5)0.0027 (5)0.0022 (4)
N40.0533 (7)0.0361 (6)0.0453 (7)0.0042 (5)0.0081 (5)0.0051 (5)
N50.0524 (7)0.0387 (6)0.0450 (6)0.0034 (5)0.0080 (5)0.0001 (5)
C10.0489 (8)0.0545 (8)0.0434 (8)0.0071 (7)0.0036 (6)0.0008 (6)
C20.0642 (10)0.0800 (13)0.0525 (10)0.0130 (9)0.0134 (8)0.0017 (9)
C30.0645 (11)0.0970 (15)0.0574 (11)0.0116 (10)0.0188 (9)0.0053 (10)
C40.0572 (10)0.0880 (14)0.0688 (12)0.0038 (10)0.0142 (9)0.0243 (11)
C50.0539 (9)0.0595 (10)0.0681 (11)0.0048 (8)0.0074 (8)0.0158 (8)
C60.0429 (7)0.0524 (8)0.0491 (8)0.0068 (6)0.0025 (6)0.0079 (6)
C70.0452 (7)0.0374 (7)0.0438 (7)0.0047 (6)0.0005 (6)0.0003 (5)
C80.0449 (7)0.0379 (7)0.0403 (7)0.0060 (6)0.0005 (5)0.0001 (5)
C90.0589 (8)0.0353 (7)0.0522 (8)0.0058 (6)0.0058 (7)0.0029 (6)
C100.0638 (9)0.0345 (7)0.0552 (9)0.0002 (7)0.0097 (7)0.0018 (6)
C110.0568 (8)0.0379 (7)0.0498 (8)0.0027 (6)0.0110 (7)0.0047 (6)
C120.0461 (7)0.0363 (6)0.0410 (7)0.0056 (6)0.0025 (5)0.0021 (5)
C130.0451 (7)0.0354 (6)0.0424 (7)0.0034 (5)0.0038 (5)0.0042 (5)
C140.0520 (8)0.0401 (7)0.0423 (7)0.0064 (6)0.0018 (6)0.0031 (6)
C150.0625 (9)0.0558 (9)0.0554 (9)0.0064 (8)0.0111 (7)0.0087 (7)
C160.0759 (11)0.0624 (10)0.0662 (11)0.0187 (9)0.0073 (9)0.0187 (9)
C170.0898 (13)0.0429 (8)0.0714 (12)0.0168 (9)0.0015 (10)0.0101 (8)
C180.0761 (11)0.0375 (7)0.0587 (10)0.0090 (7)0.0035 (8)0.0002 (7)
C190.0543 (8)0.0387 (7)0.0430 (7)0.0078 (6)0.0006 (6)0.0009 (6)
O10.0873 (9)0.0462 (6)0.0612 (7)0.0133 (6)0.0288 (7)0.0021 (5)
O20.0936 (9)0.0482 (6)0.0773 (8)0.0008 (6)0.0494 (7)0.0055 (6)
C200.0528 (8)0.0410 (7)0.0520 (8)0.0055 (6)0.0152 (6)0.0062 (6)
C210.0598 (9)0.0492 (8)0.0475 (9)0.0009 (7)0.0154 (7)0.0048 (6)
C220.0600 (9)0.0463 (8)0.0543 (9)0.0033 (7)0.0209 (8)0.0062 (7)
O1W0.1059 (10)0.0511 (7)0.0632 (8)0.0195 (7)0.0014 (7)0.0007 (6)
O2W0.0710 (8)0.0589 (7)0.0809 (10)0.0058 (6)0.0037 (7)0.0200 (7)
Geometric parameters (Å, º) top
N1—C71.3166 (19)C11—C121.3957 (19)
N1—C11.388 (2)C11—H11A0.917 (19)
N2—C71.3664 (17)C12—C131.459 (2)
N2—C61.375 (2)C14—C151.394 (2)
N2—H40.95 (2)C14—C191.395 (2)
N3—C81.3375 (18)C15—C161.381 (3)
N3—C121.3381 (19)C15—H15A1.00 (2)
N4—C131.3617 (17)C16—C171.397 (3)
N4—C191.376 (2)C16—H16A0.96 (2)
N4—H50.88 (2)C17—C181.370 (3)
N5—C131.3201 (18)C17—H17A1.00 (2)
N5—C141.3911 (18)C18—C191.393 (2)
C1—C21.394 (2)C18—H18A0.98 (2)
C1—C61.398 (2)O1—C201.3109 (19)
C2—C31.383 (3)O1—H10.873 (10)
C2—H2B0.99 (3)O2—C201.203 (2)
C3—C41.386 (3)C20—C211.498 (2)
C3—H3B0.97 (2)C21—C221.514 (2)
C4—C51.388 (3)C21—H21A0.94 (2)
C4—H4B1.03 (2)C21—H21B1.07 (2)
C5—C61.394 (2)C22—C22i1.522 (3)
C5—H5B0.94 (2)C22—H22A1.001 (19)
C7—C81.461 (2)C22—H22B1.02 (2)
C8—C91.3927 (19)O1W—H1WA0.854 (10)
C9—C101.376 (2)O1W—H1WB0.848 (9)
C9—H9A0.935 (18)O2W—H2WB0.860 (10)
C10—C111.374 (2)O2W—H2WA0.865 (10)
C10—H10A1.012 (18)
C7—N1—C1104.88 (12)N3—C12—C11122.93 (14)
C7—N2—C6106.77 (13)N3—C12—C13115.23 (12)
C7—N2—H4120.0 (12)C11—C12—C13121.82 (14)
C6—N2—H4133.2 (12)N5—C13—N4112.69 (13)
C8—N3—C12117.85 (12)N5—C13—C12126.24 (12)
C13—N4—C19107.10 (13)N4—C13—C12121.05 (13)
C13—N4—H5125.1 (13)N5—C14—C15129.82 (15)
C19—N4—H5127.8 (13)N5—C14—C19109.63 (13)
C13—N5—C14105.00 (12)C15—C14—C19120.50 (15)
N1—C1—C2129.23 (17)C16—C15—C14117.41 (17)
N1—C1—C6109.80 (14)C16—C15—H15A124.0 (13)
C2—C1—C6120.96 (16)C14—C15—H15A118.6 (13)
C3—C2—C1117.3 (2)C15—C16—C17121.28 (17)
C3—C2—H2B122.5 (16)C15—C16—H16A120.3 (13)
C1—C2—H2B120.2 (16)C17—C16—H16A118.4 (13)
C2—C3—C4121.2 (2)C18—C17—C16122.09 (16)
C2—C3—H3B119.3 (13)C18—C17—H17A119.2 (12)
C4—C3—H3B119.5 (13)C16—C17—H17A118.7 (12)
C3—C4—C5122.70 (18)C17—C18—C19116.66 (17)
C3—C4—H4B117.8 (13)C17—C18—H18A123.8 (12)
C5—C4—H4B119.5 (13)C19—C18—H18A119.6 (12)
C4—C5—C6115.93 (19)N4—C19—C18132.36 (15)
C4—C5—H5B121.0 (13)N4—C19—C14105.57 (12)
C6—C5—H5B123.1 (13)C18—C19—C14122.03 (15)
N2—C6—C5132.52 (16)C20—O1—H1113.3 (16)
N2—C6—C1105.55 (13)O2—C20—O1123.00 (14)
C5—C6—C1121.93 (17)O2—C20—C21124.71 (14)
N1—C7—N2112.99 (13)O1—C20—C21112.28 (14)
N1—C7—C8125.67 (12)C20—C21—C22114.80 (14)
N2—C7—C8121.32 (13)C20—C21—H21A108.3 (13)
N3—C8—C9122.74 (14)C22—C21—H21A110.4 (13)
N3—C8—C7115.52 (12)C20—C21—H21B106.6 (10)
C9—C8—C7121.71 (13)C22—C21—H21B111.9 (11)
C10—C9—C8118.51 (14)H21A—C21—H21B104.2 (17)
C10—C9—H9A124.2 (11)C21—C22—C22i111.97 (18)
C8—C9—H9A117.3 (11)C21—C22—H22A109.3 (11)
C11—C10—C9119.71 (13)C22i—C22—H22A109.8 (11)
C11—C10—H10A120.1 (10)C21—C22—H22B110.5 (11)
C9—C10—H10A120.2 (10)C22i—C22—H22B108.1 (11)
C10—C11—C12118.22 (14)H22A—C22—H22B107.0 (15)
C10—C11—H11A125.1 (11)H1WA—O1W—H1WB108.7 (18)
C12—C11—H11A116.6 (11)H2WB—O2W—H2WA102.4 (18)
Symmetry code: (i) x+2, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H4···O2W0.95 (2)2.16 (2)3.084 (2)163.3 (18)
N4—H5···O2W0.88 (2)2.08 (2)2.945 (2)167.6 (18)
O1—H1···N50.87 (1)1.83 (1)2.6731 (19)163 (2)
O1W—H1WA···N1ii0.85 (1)1.99 (1)2.8169 (18)162 (2)
O1W—H1WB···O2iii0.85 (1)1.99 (1)2.815 (2)165 (2)
O2W—H2WB···O1Wiv0.86 (1)2.05 (1)2.898 (2)170 (3)
O2W—H2WA···O1Wv0.87 (1)2.01 (1)2.867 (2)171 (3)
Symmetry codes: (ii) x, y, z+1; (iii) x+1, y, z+1; (iv) x, y+1, z+1; (v) x, y+1, z1.

Experimental details

Crystal data
Chemical formula2C19H13N5·C6H10O4·4H2O
Mr840.90
Crystal system, space groupTriclinic, P1
Temperature (K)295
a, b, c (Å)9.0709 (18), 9.6882 (19), 12.311 (3)
α, β, γ (°)88.93 (3), 83.12 (3), 75.14 (3)
V3)1038.1 (4)
Z1
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.25 × 0.18 × 0.16
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
10214, 4705, 3555
Rint0.024
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.163, 1.15
No. of reflections4705
No. of parameters368
No. of restraints7
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.36, 0.19

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), WinGX (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H4···O2W0.95 (2)2.16 (2)3.084 (2)163.3 (18)
N4—H5···O2W0.88 (2)2.08 (2)2.945 (2)167.6 (18)
O1—H1···N50.873 (10)1.825 (12)2.6731 (19)163 (2)
O1W—H1WA···N1i0.854 (10)1.993 (11)2.8169 (18)162 (2)
O1W—H1WB···O2ii0.848 (9)1.989 (11)2.815 (2)165 (2)
O2W—H2WB···O1Wiii0.860 (10)2.046 (12)2.898 (2)170 (3)
O2W—H2WA···O1Wiv0.865 (10)2.009 (11)2.867 (2)171 (3)
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z+1; (iii) x, y+1, z+1; (iv) x, y+1, z1.
 

Acknowledgements

The authors would like to thank the National Natural Science Foundation of China (51003010), the Natural Science Foundation of Jilin Province (201115178) and the Science and Technology Development Project of Jilin Province (SKLSSM201132).

References

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