organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

N,N-Di­ethyl-2-hy­dr­oxy­ethanaminium 5-(5-chloro-2,4-di­nitro­phen­yl)-2,6-dioxo-1,2,3,6-tetra­hydro­pyrimidin-4-olate hemihydrate

aPostgraduate and Research Department of Chemistry, Seethalakshmi Ramaswami College, Tiruchirappalli 620 002, Tamil Nadu, India
*Correspondence e-mail: kalaivbalaj@yahoo.co.in

(Received 27 December 2011; accepted 25 January 2012; online 31 January 2012)

The asymmetric unit of the title salt, C6H16NO+·C10H4ClN4O7·0.5H2O, contains two cations, two anions and one water mol­ecule. In one independent anion, one nitro group is rotationally disordered over two orientations in a 0.657 (8):0.343 (8) ratio. In the crystal, inter­molecular N—H⋯O and O—H⋯O hydrogen bonds link all the components into ribbons extending along [100].

Related literature

For details of the pharmacological properties of pyrimidine derivatives, see: Hueso et al. (2003[Hueso, F., Illan, N. A., Moreno, M. N., Martinez, J. M. & Ramirez, M. J. (2003). J. Inorg. Biochem. 94, 326-334.]); Colorado & Brodbelt (1996[Colorado, A. & Brodbelt, J. (1996). J. Mass Spectrom. 31, 403-410.]); Kalaivani et al. (2008[Kalaivani, D., Malarvizhi, R. & Subbulakshmi, R. (2008). Med. Chem. Res. 17, 369-373.]); Kalaivani & Buvaneswari (2010[Kalaivani, D. & Buvaneswari, M. (2010). Recent Advances in Clinical Medicine, pp. 255-260. Cambridge, England: WSEAS Press.]). For the crystal structures of related compounds, see: Kalaivani & Malarvizhi (2009[Kalaivani, D. & Malarvizhi, R. (2009). Acta Cryst. E65, o2548.]); Buvaneswari & Kalaivani (2011[Buvaneswari, M. & Kalaivani, D. (2011). Acta Cryst. E67, o1433-o1434.]).

[Scheme 1]

Experimental

Crystal data
  • C6H16NO+·C10H4ClN4O7·0.5H2O

  • Mr = 454.83

  • Triclinic, [P \overline 1]

  • a = 12.3775 (7) Å

  • b = 12.8109 (8) Å

  • c = 13.5834 (9) Å

  • α = 101.497 (4)°

  • β = 99.142 (3)°

  • γ = 99.718 (3)°

  • V = 2038.6 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.25 mm−1

  • T = 294 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SADABS, XPREP and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.901, Tmax = 0.942

  • 36654 measured reflections

  • 7179 independent reflections

  • 5639 reflections with I > 2σ(I)

  • Rint = 0.031

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.138

  • S = 1.07

  • 7179 reflections

  • 598 parameters

  • 4 restraints

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

  • Δρmax = 0.72 e Å−3

  • Δρmin = −0.32 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N5—H5⋯O9i 0.91 1.85 2.749 (2) 167
O8—H8⋯O1ii 0.82 1.98 2.674 (2) 141
O9—H9A⋯O2 0.84 (1) 1.85 (1) 2.691 (2) 171 (3)
O9—H9B⋯O10 0.85 (1) 2.11 (2) 2.850 (2) 146 (3)
N2—H2⋯O3ii 0.85 (3) 1.99 (3) 2.826 (2) 168 (2)
N1—H1⋯O10 0.84 (2) 2.10 (2) 2.933 (2) 171 (2)
N10—H10⋯O12 0.91 1.85 2.698 (2) 154
O17—H17⋯O8iii 0.82 1.91 2.667 (2) 153
N7—H7⋯O17 0.84 (3) 2.07 (3) 2.911 (2) 176 (2)
N6—H6A⋯O1 0.81 (2) 2.16 (2) 2.947 (2) 167 (2)
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+1, -z; (iii) x+1, y, z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SADABS, XPREP and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004[Bruker (2004). APEX2, SADABS, XPREP and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker, 2004[Bruker (2004). APEX2, SADABS, XPREP and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Pyrimidine derivatives play a significant role in many biological systems (Hueso et al., 2003). Barbiturates are pyrimidine derivatives which have been used as hypnotic drugs, anaesthetics, sleeping agents and for the treatment of anxiety, epilepsy and other psychiatric disorders (Colorado & Brodbelt, 1996). In continuation of our systematic studies of molecular salts containing various derivatives of barbiturates (Kalaivani et al., 2008; Kalaivani & Malarvizhi, 2009; Kalaivani & Buvaneswari, 2010; Buvaneswari & Kalaivani, 2011), we present here the title compound (I).

In (I) (Fig. 1), all bond lengths and angles are normal and comparable with those observed in the related compounds (Kalaivani & Malarvizhi, 2009; Buvaneswari & Kalaivani, 2011). The crystal packing (Fig. 2) exhibits a number of N—H···O and O—H···O hydrogen bonds with various ring motifs such as R22(8), R22(9), R32(8) and R44(13), respectively. These hydrogen bonds link all moieties into ribbons extended in [100].

Related literature top

For details of the pharmacological properties of pyrimidine derivatives, see: Hueso et al. (2003); Colorado & Brodbelt (1996); Kalaivani et al. (2008); Kalaivani & Buvaneswari (2010). For the crystal structures of related compounds, see: Kalaivani & Malarvizhi (2009); Buvaneswari & Kalaivani (2011).

Experimental top

Analytical grade 1,3-dichloro-4,6-dinitrobenzene (DCDNB) and barbituric acid were used as supplied by Aldrich company. N,N-Diethylethanolamine was distilled under reduced pressure and the fraction boiling over at its boiling point was used for the preparation of the title molecular salt. DCDNB (2.01 g, 0.01 mol) in 15 ml absolute ethanol was mixed with barbituric acid (1.28 g, 0.01 mol) in 30 ml of absolute ethanol. N,N-diethylethanolamine (2.36 g, 0.02 mol) was added to the above mixture at 313 K and shaken well for 5–6 h. The solution was filtered and kept as such at room temperature for 48 h. On standing, reddish orange crystals come out from the solution. The crystals were powdered well and washed with copious amount of ethanol and dry ether and recrystallized from absolute alcohol (yield of pure crystals 80%, m.p. 503 K). Good quality crystals (red orange blocks) for single-crystal X-ray studies were obtained by slow evaporation of ethanol at room temperature.

Refinement top

The H atoms of the water molecule (H9A and H9B) and pyrimidine N atoms (H1, H2, H6A and H7) were located in difference Fourier maps and refined as restrained and riding in their as-found relative positions. The rest H atoms were positioned geometrically and were refined using a riding model.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The content of asymmetric part of (I) showing the atomic numbering and 30% probability displacement ellipsoids. For the disordered nitro group, only major part is shown.
[Figure 2] Fig. 2. A portion of the crystal packing showing hydrogen bonds as dotted lines.
N,N-Diethyl-2-hydroxyethanaminium 5-(5-chloro-2,4-dinitrophenyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-olate hemihydrate top
Crystal data top
C6H16NO+·C10H4ClN4O7·0.5H2OZ = 4
Mr = 454.83F(000) = 948
Triclinic, P1Dx = 1.482 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.3775 (7) ÅCell parameters from 6078 reflections
b = 12.8109 (8) Åθ = 2.5–27.0°
c = 13.5834 (9) ŵ = 0.25 mm1
α = 101.497 (4)°T = 294 K
β = 99.142 (3)°Block, red
γ = 99.718 (3)°0.30 × 0.25 × 0.20 mm
V = 2038.6 (2) Å3
Data collection top
Bruker Kappa APEXII CCD
diffractometer
7179 independent reflections
Radiation source: fine-focus sealed tube5639 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ω and ϕ scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
h = 1414
Tmin = 0.901, Tmax = 0.942k = 1515
36654 measured reflectionsl = 1616
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0773P)2 + 0.6949P]
where P = (Fo2 + 2Fc2)/3
7179 reflections(Δ/σ)max < 0.001
598 parametersΔρmax = 0.72 e Å3
4 restraintsΔρmin = 0.32 e Å3
Crystal data top
C6H16NO+·C10H4ClN4O7·0.5H2Oγ = 99.718 (3)°
Mr = 454.83V = 2038.6 (2) Å3
Triclinic, P1Z = 4
a = 12.3775 (7) ÅMo Kα radiation
b = 12.8109 (8) ŵ = 0.25 mm1
c = 13.5834 (9) ÅT = 294 K
α = 101.497 (4)°0.30 × 0.25 × 0.20 mm
β = 99.142 (3)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
7179 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
5639 reflections with I > 2σ(I)
Tmin = 0.901, Tmax = 0.942Rint = 0.031
36654 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0434 restraints
wR(F2) = 0.138H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.72 e Å3
7179 reflectionsΔρmin = 0.32 e Å3
598 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*/UeqOcc. (<1)
C10.73604 (16)0.44594 (17)0.05043 (16)0.0343 (5)
C20.60151 (16)0.40344 (17)0.05684 (15)0.0309 (4)
C30.65908 (16)0.32478 (16)0.08526 (15)0.0307 (4)
C40.75520 (16)0.30658 (16)0.04682 (16)0.0330 (4)
C50.62072 (15)0.26499 (16)0.15797 (15)0.0309 (4)
C60.59379 (16)0.32162 (17)0.24693 (16)0.0331 (4)
H60.60240.39680.25820.040*
C70.55516 (17)0.27072 (18)0.31856 (16)0.0369 (5)
C80.54654 (19)0.15898 (19)0.30541 (17)0.0407 (5)
C90.57638 (18)0.10095 (19)0.22112 (18)0.0423 (5)
H90.57360.02670.21310.051*
C100.61032 (17)0.15297 (17)0.14886 (16)0.0356 (5)
C110.3083 (2)0.2680 (2)0.1612 (2)0.0532 (6)
H11A0.36350.33220.19950.064*
H11B0.34760.21100.13880.064*
C120.23267 (19)0.23115 (19)0.23035 (18)0.0448 (5)
H12A0.27570.20630.28390.054*
H12B0.20420.29250.26290.054*
C130.1698 (2)0.0418 (2)0.1186 (2)0.0518 (6)
H13A0.10320.00710.07560.062*
H13B0.21910.06280.07390.062*
C140.2266 (3)0.0185 (3)0.1866 (3)0.0890 (11)
H14A0.29440.02800.22780.133*
H14B0.24410.08130.14560.133*
H14C0.17810.04140.23030.133*
C150.0554 (2)0.1188 (2)0.2403 (2)0.0544 (6)
H15A0.03670.18660.27170.065*
H15B0.09040.08940.29470.065*
C160.0505 (3)0.0396 (3)0.1822 (3)0.0785 (9)
H16A0.08100.06440.12360.118*
H16B0.10390.03500.22610.118*
H16C0.03410.03090.16000.118*
N10.78912 (15)0.37048 (15)0.01912 (14)0.0371 (4)
N20.64328 (14)0.45918 (15)0.01195 (14)0.0347 (4)
N30.62568 (17)0.08057 (16)0.05553 (17)0.0474 (5)
N40.5033 (2)0.0960 (2)0.37474 (18)0.0619 (6)
N50.13683 (15)0.14164 (15)0.17278 (14)0.0383 (4)
H50.10020.16820.12280.046*
O10.77048 (13)0.49917 (13)0.10940 (13)0.0454 (4)
O20.81174 (12)0.24002 (13)0.06849 (13)0.0452 (4)
O30.51542 (12)0.42531 (13)0.08530 (12)0.0404 (4)
O40.58787 (16)0.09712 (15)0.02727 (14)0.0595 (5)
O50.67161 (17)0.00520 (15)0.06664 (17)0.0685 (6)
O60.5307 (3)0.0114 (2)0.3777 (2)0.1097 (10)
O70.4287 (2)0.12591 (19)0.41688 (18)0.0825 (7)
O80.24764 (14)0.29216 (14)0.07518 (13)0.0521 (4)
H80.21580.34150.09390.078*
O91.00189 (14)0.19327 (14)0.01618 (15)0.0494 (4)
Cl10.52193 (6)0.35212 (5)0.42199 (5)0.05531 (19)
H9A0.9462 (17)0.210 (2)0.040 (2)0.069 (9)*
H9B1.030 (2)0.241 (2)0.013 (3)0.100 (13)*
H20.604 (2)0.501 (2)0.0340 (18)0.042 (7)*
H10.847 (2)0.3646 (18)0.0432 (17)0.034 (6)*
C171.03464 (17)0.41704 (18)0.14752 (16)0.0368 (5)
C181.16333 (15)0.44983 (15)0.26248 (15)0.0288 (4)
C191.10360 (16)0.52326 (16)0.29751 (15)0.0305 (4)
C201.01060 (16)0.54779 (17)0.25484 (15)0.0324 (4)
C211.13552 (15)0.57684 (16)0.37742 (15)0.0298 (4)
C221.13816 (17)0.68886 (17)0.36557 (17)0.0349 (5)
H221.12190.72710.30590.042*
C231.16361 (19)0.74390 (17)0.43818 (18)0.0413 (5)
C241.19176 (19)0.68958 (19)0.52631 (18)0.0438 (5)
C251.19514 (18)0.58186 (18)0.54005 (17)0.0394 (5)
H251.21680.54570.59780.047*
C261.16608 (16)0.52740 (16)0.46732 (15)0.0313 (4)
C271.3675 (3)0.2472 (3)0.1336 (2)0.0674 (8)
H27A1.40130.21120.08390.081*
H27B1.41040.32100.11990.081*
C281.3701 (3)0.1885 (3)0.2380 (2)0.0689 (8)
H28A1.32010.11780.25340.083*
H28B1.44510.17620.23950.083*
C291.4321 (2)0.2946 (2)0.3634 (2)0.0583 (7)
H29A1.46870.23760.39160.070*
H29B1.40180.32480.41920.070*
C301.5159 (3)0.3808 (3)0.2878 (3)0.0836 (10)
H30A1.47890.43180.25180.125*
H30B1.56640.41780.32260.125*
H30C1.55710.34890.23990.125*
C311.2477 (3)0.1671 (2)0.4101 (2)0.0680 (8)
H31A1.23990.20050.46820.082*
H31B1.27270.09970.43090.082*
C321.1376 (3)0.1425 (3)0.3805 (3)0.0822 (10)
H32A1.14500.10890.32330.123*
H32B1.08490.09380.43740.123*
H32C1.11170.20880.36180.123*
N60.98182 (15)0.49133 (16)0.18171 (15)0.0394 (4)
N71.12560 (14)0.40106 (15)0.18818 (14)0.0353 (4)
N81.16366 (16)0.40985 (15)0.49451 (13)0.0381 (4)
N91.2163 (3)0.7445 (2)0.6078 (2)0.0779 (8)
N101.33782 (18)0.24545 (16)0.31949 (16)0.0493 (5)
H101.30600.30040.29170.059*
O101.00397 (14)0.36887 (15)0.08398 (13)0.0519 (4)
O110.95065 (12)0.61060 (13)0.27829 (12)0.0418 (4)
O121.24892 (11)0.42489 (11)0.29138 (11)0.0335 (3)
O131.08502 (14)0.34754 (13)0.48101 (13)0.0483 (4)
O141.24008 (15)0.38142 (14)0.53307 (13)0.0555 (5)
O151.1439 (4)0.7960 (5)0.6401 (4)0.118 (2)0.670 (9)
O161.2847 (6)0.7283 (7)0.6494 (7)0.142 (5)0.670 (9)
O15'1.3101 (9)0.8218 (9)0.5731 (7)0.125 (5)0.330 (9)
O16'1.2011 (14)0.7054 (10)0.6879 (7)0.133 (8)0.330 (9)
O171.25677 (16)0.24953 (16)0.12333 (14)0.0623 (5)
H171.25640.28340.06550.094*
Cl21.16163 (7)0.88047 (5)0.41687 (6)0.0707 (2)
H71.161 (2)0.355 (2)0.1702 (19)0.043 (7)*
H6A0.928 (2)0.5042 (19)0.1581 (18)0.036 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0309 (10)0.0399 (12)0.0377 (11)0.0116 (9)0.0126 (9)0.0136 (9)
C20.0273 (10)0.0387 (11)0.0304 (10)0.0113 (8)0.0090 (8)0.0106 (9)
C30.0272 (10)0.0351 (11)0.0329 (11)0.0087 (8)0.0094 (8)0.0104 (9)
C40.0283 (10)0.0350 (11)0.0401 (11)0.0101 (9)0.0107 (9)0.0130 (9)
C50.0221 (9)0.0381 (11)0.0357 (11)0.0096 (8)0.0062 (8)0.0128 (9)
C60.0286 (10)0.0380 (11)0.0356 (11)0.0109 (8)0.0074 (9)0.0109 (9)
C70.0328 (10)0.0487 (13)0.0322 (11)0.0118 (9)0.0088 (9)0.0116 (9)
C80.0422 (12)0.0496 (13)0.0372 (12)0.0119 (10)0.0125 (10)0.0206 (10)
C90.0433 (12)0.0390 (12)0.0518 (14)0.0142 (10)0.0144 (11)0.0182 (10)
C100.0322 (10)0.0397 (12)0.0382 (12)0.0115 (9)0.0117 (9)0.0098 (9)
C110.0386 (12)0.0547 (15)0.0649 (17)0.0085 (11)0.0021 (12)0.0181 (13)
C120.0474 (13)0.0452 (13)0.0415 (13)0.0132 (10)0.0049 (10)0.0094 (10)
C130.0555 (14)0.0512 (14)0.0495 (14)0.0158 (12)0.0194 (12)0.0027 (11)
C140.101 (3)0.070 (2)0.103 (3)0.051 (2)0.014 (2)0.0113 (19)
C150.0640 (16)0.0570 (15)0.0549 (15)0.0191 (13)0.0339 (13)0.0196 (12)
C160.0639 (18)0.088 (2)0.088 (2)0.0028 (16)0.0363 (17)0.0307 (19)
N10.0301 (9)0.0450 (11)0.0484 (11)0.0180 (8)0.0207 (8)0.0201 (9)
N20.0307 (9)0.0432 (10)0.0410 (10)0.0189 (8)0.0147 (8)0.0196 (8)
N30.0462 (11)0.0405 (11)0.0575 (14)0.0067 (9)0.0253 (10)0.0060 (10)
N40.0846 (17)0.0630 (15)0.0533 (13)0.0228 (13)0.0316 (12)0.0280 (11)
N50.0423 (10)0.0432 (10)0.0362 (10)0.0150 (8)0.0146 (8)0.0148 (8)
O10.0426 (8)0.0569 (10)0.0557 (10)0.0232 (7)0.0266 (8)0.0332 (8)
O20.0372 (8)0.0490 (9)0.0673 (11)0.0240 (7)0.0249 (8)0.0309 (8)
O30.0340 (8)0.0566 (10)0.0459 (9)0.0254 (7)0.0198 (7)0.0246 (7)
O40.0692 (12)0.0605 (12)0.0431 (10)0.0026 (9)0.0183 (9)0.0026 (9)
O50.0776 (13)0.0476 (11)0.0946 (15)0.0287 (10)0.0454 (12)0.0139 (10)
O60.166 (3)0.0938 (18)0.129 (2)0.0676 (19)0.090 (2)0.0805 (18)
O70.1039 (17)0.0817 (15)0.0758 (14)0.0151 (13)0.0538 (13)0.0256 (12)
O80.0519 (10)0.0570 (10)0.0532 (10)0.0116 (8)0.0154 (8)0.0223 (8)
O90.0389 (9)0.0554 (10)0.0675 (12)0.0219 (8)0.0200 (8)0.0280 (9)
Cl10.0693 (4)0.0612 (4)0.0400 (3)0.0161 (3)0.0252 (3)0.0086 (3)
C170.0343 (11)0.0450 (12)0.0384 (12)0.0144 (9)0.0127 (9)0.0169 (10)
C180.0287 (10)0.0291 (10)0.0292 (10)0.0074 (8)0.0068 (8)0.0059 (8)
C190.0308 (10)0.0320 (10)0.0326 (10)0.0107 (8)0.0094 (8)0.0103 (8)
C200.0315 (10)0.0349 (11)0.0338 (11)0.0121 (9)0.0078 (9)0.0096 (9)
C210.0237 (9)0.0319 (10)0.0345 (11)0.0083 (8)0.0041 (8)0.0082 (8)
C220.0342 (11)0.0327 (11)0.0408 (12)0.0101 (9)0.0106 (9)0.0101 (9)
C230.0428 (12)0.0297 (11)0.0535 (14)0.0083 (9)0.0098 (10)0.0140 (10)
C240.0460 (13)0.0455 (13)0.0468 (13)0.0073 (10)0.0150 (11)0.0241 (11)
C250.0381 (11)0.0443 (13)0.0388 (12)0.0096 (10)0.0124 (10)0.0117 (10)
C260.0300 (10)0.0309 (10)0.0345 (11)0.0084 (8)0.0067 (8)0.0096 (9)
C270.0680 (18)0.088 (2)0.0527 (16)0.0331 (16)0.0112 (14)0.0186 (15)
C280.086 (2)0.0715 (19)0.0711 (19)0.0483 (17)0.0276 (16)0.0301 (16)
C290.0615 (16)0.0704 (18)0.0538 (16)0.0268 (14)0.0279 (13)0.0156 (13)
C300.0648 (19)0.096 (3)0.080 (2)0.0135 (18)0.0264 (17)0.0080 (19)
C310.094 (2)0.0429 (15)0.0690 (19)0.0187 (15)0.0204 (17)0.0095 (13)
C320.081 (2)0.0540 (18)0.103 (3)0.0091 (16)0.002 (2)0.0162 (18)
N60.0351 (10)0.0512 (12)0.0476 (11)0.0238 (9)0.0221 (9)0.0245 (9)
N70.0353 (9)0.0413 (10)0.0408 (10)0.0191 (8)0.0156 (8)0.0204 (8)
N80.0470 (11)0.0368 (10)0.0306 (9)0.0148 (9)0.0029 (8)0.0070 (8)
N90.118 (2)0.0601 (16)0.078 (2)0.0223 (17)0.0525 (19)0.0383 (16)
N100.0656 (13)0.0449 (11)0.0542 (12)0.0313 (10)0.0286 (10)0.0203 (10)
O100.0513 (9)0.0700 (11)0.0608 (11)0.0309 (9)0.0327 (8)0.0438 (9)
O110.0402 (8)0.0490 (9)0.0500 (9)0.0259 (7)0.0164 (7)0.0231 (7)
O120.0322 (7)0.0352 (8)0.0412 (8)0.0154 (6)0.0153 (6)0.0138 (6)
O130.0550 (10)0.0349 (8)0.0498 (10)0.0011 (7)0.0026 (8)0.0108 (7)
O140.0700 (11)0.0579 (11)0.0498 (10)0.0366 (9)0.0221 (9)0.0103 (8)
O150.149 (4)0.155 (5)0.118 (4)0.090 (3)0.066 (3)0.110 (4)
O160.160 (6)0.184 (9)0.188 (9)0.113 (7)0.139 (7)0.141 (8)
O15'0.154 (9)0.103 (7)0.093 (6)0.068 (6)0.040 (6)0.032 (6)
O16'0.221 (16)0.107 (9)0.039 (5)0.058 (11)0.027 (7)0.020 (4)
O170.0757 (13)0.0789 (13)0.0519 (11)0.0432 (11)0.0218 (9)0.0299 (10)
Cl20.0971 (6)0.0333 (3)0.0919 (6)0.0188 (3)0.0292 (4)0.0254 (3)
Geometric parameters (Å, º) top
C1—O11.231 (2)C17—O101.228 (2)
C1—N11.355 (3)C17—N61.356 (3)
C1—N21.357 (3)C17—N71.358 (3)
C2—O31.246 (2)C18—O121.255 (2)
C2—N21.395 (3)C18—N71.389 (3)
C2—C31.408 (3)C18—C191.400 (3)
C3—C41.409 (3)C19—C201.422 (3)
C3—C51.454 (3)C19—C211.465 (3)
C4—O21.241 (2)C20—O111.236 (2)
C4—N11.394 (3)C20—N61.396 (3)
C5—C101.398 (3)C21—C261.398 (3)
C5—C61.399 (3)C21—C221.406 (3)
C6—C71.377 (3)C22—C231.368 (3)
C6—H60.9300C22—H220.9300
C7—C81.390 (3)C23—C241.386 (3)
C7—Cl11.725 (2)C23—Cl21.721 (2)
C8—C91.374 (3)C24—C251.364 (3)
C8—N41.464 (3)C24—N91.468 (3)
C9—C101.372 (3)C25—C261.377 (3)
C9—H90.9300C25—H250.9300
C10—N31.473 (3)C26—N81.471 (3)
C11—O81.403 (3)C27—O171.404 (3)
C11—C121.512 (3)C27—C281.476 (4)
C11—H11A0.9700C27—H27A0.9700
C11—H11B0.9700C27—H27B0.9700
C12—N51.491 (3)C28—N101.482 (3)
C12—H12A0.9700C28—H28A0.9700
C12—H12B0.9700C28—H28B0.9700
C13—C141.486 (4)C29—C301.474 (4)
C13—N51.497 (3)C29—N101.495 (3)
C13—H13A0.9700C29—H29A0.9700
C13—H13B0.9700C29—H29B0.9700
C14—H14A0.9600C30—H30A0.9600
C14—H14B0.9600C30—H30B0.9600
C14—H14C0.9600C30—H30C0.9600
C15—N51.498 (3)C31—C321.482 (5)
C15—C161.508 (4)C31—N101.568 (4)
C15—H15A0.9700C31—H31A0.9700
C15—H15B0.9700C31—H31B0.9700
C16—H16A0.9600C32—H32A0.9600
C16—H16B0.9600C32—H32B0.9600
C16—H16C0.9600C32—H32C0.9600
N1—H10.84 (2)N6—H6A0.81 (2)
N2—H20.85 (3)N7—H70.84 (3)
N3—O41.221 (3)N8—O131.213 (2)
N3—O51.223 (3)N8—O141.225 (2)
N4—O61.194 (3)N9—O16'1.076 (9)
N4—O71.235 (3)N9—O161.115 (5)
N5—H50.9100N9—O151.275 (5)
O8—H80.8200N9—O15'1.343 (8)
O9—H9A0.844 (10)N10—H100.9100
O9—H9B0.847 (10)O17—H170.8200
O1—C1—N1121.94 (18)O12—C18—N7116.88 (17)
O1—C1—N2122.51 (19)O12—C18—C19125.81 (18)
N1—C1—N2115.54 (18)N7—C18—C19117.30 (17)
O3—C2—N2117.45 (17)C18—C19—C20120.00 (18)
O3—C2—C3125.94 (18)C18—C19—C21121.25 (17)
N2—C2—C3116.58 (16)C20—C19—C21118.75 (17)
C2—C3—C4120.63 (18)O11—C20—N6116.96 (17)
C2—C3—C5119.26 (17)O11—C20—C19126.90 (19)
C4—C3—C5120.07 (17)N6—C20—C19116.09 (17)
O2—C4—N1118.45 (17)C26—C21—C22114.50 (18)
O2—C4—C3125.05 (19)C26—C21—C19126.22 (17)
N1—C4—C3116.49 (17)C22—C21—C19119.28 (17)
C10—C5—C6115.15 (18)C23—C22—C21122.7 (2)
C10—C5—C3125.52 (18)C23—C22—H22118.6
C6—C5—C3119.31 (18)C21—C22—H22118.6
C7—C6—C5122.8 (2)C22—C23—C24119.8 (2)
C7—C6—H6118.6C22—C23—Cl2118.85 (18)
C5—C6—H6118.6C24—C23—Cl2121.37 (17)
C6—C7—C8119.43 (19)C25—C24—C23120.1 (2)
C6—C7—Cl1116.87 (17)C25—C24—N9118.2 (2)
C8—C7—Cl1123.70 (16)C23—C24—N9121.7 (2)
C9—C8—C7119.59 (19)C24—C25—C26119.1 (2)
C9—C8—N4116.3 (2)C24—C25—H25120.5
C7—C8—N4124.1 (2)C26—C25—H25120.5
C10—C9—C8119.8 (2)C25—C26—C21123.73 (19)
C10—C9—H9120.1C25—C26—N8114.20 (18)
C8—C9—H9120.1C21—C26—N8121.99 (17)
C9—C10—C5123.18 (19)O17—C27—C28110.3 (3)
C9—C10—N3114.93 (19)O17—C27—H27A109.6
C5—C10—N3121.68 (18)C28—C27—H27A109.6
O8—C11—C12111.63 (19)O17—C27—H27B109.6
O8—C11—H11A109.3C28—C27—H27B109.6
C12—C11—H11A109.3H27A—C27—H27B108.1
O8—C11—H11B109.3C27—C28—N10114.6 (2)
C12—C11—H11B109.3C27—C28—H28A108.6
H11A—C11—H11B108.0N10—C28—H28A108.6
N5—C12—C11111.96 (19)C27—C28—H28B108.6
N5—C12—H12A109.2N10—C28—H28B108.6
C11—C12—H12A109.2H28A—C28—H28B107.6
N5—C12—H12B109.2C30—C29—N10113.5 (2)
C11—C12—H12B109.2C30—C29—H29A108.9
H12A—C12—H12B107.9N10—C29—H29A108.9
C14—C13—N5115.1 (2)C30—C29—H29B108.9
C14—C13—H13A108.5N10—C29—H29B108.9
N5—C13—H13A108.5H29A—C29—H29B107.7
C14—C13—H13B108.5C29—C30—H30A109.5
N5—C13—H13B108.5C29—C30—H30B109.5
H13A—C13—H13B107.5H30A—C30—H30B109.5
C13—C14—H14A109.5C29—C30—H30C109.5
C13—C14—H14B109.5H30A—C30—H30C109.5
H14A—C14—H14B109.5H30B—C30—H30C109.5
C13—C14—H14C109.5C32—C31—N10111.7 (2)
H14A—C14—H14C109.5C32—C31—H31A109.3
H14B—C14—H14C109.5N10—C31—H31A109.3
N5—C15—C16112.4 (2)C32—C31—H31B109.3
N5—C15—H15A109.1N10—C31—H31B109.3
C16—C15—H15A109.1H31A—C31—H31B107.9
N5—C15—H15B109.1C31—C32—H32A109.5
C16—C15—H15B109.1C31—C32—H32B109.5
H15A—C15—H15B107.9H32A—C32—H32B109.5
C15—C16—H16A109.5C31—C32—H32C109.5
C15—C16—H16B109.5H32A—C32—H32C109.5
H16A—C16—H16B109.5H32B—C32—H32C109.5
C15—C16—H16C109.5C17—N6—C20126.19 (18)
H16A—C16—H16C109.5C17—N6—H6A117.4 (17)
H16B—C16—H16C109.5C20—N6—H6A116.4 (17)
C1—N1—C4125.43 (17)C17—N7—C18125.73 (18)
C1—N1—H1113.6 (15)C17—N7—H7118.2 (17)
C4—N1—H1120.9 (15)C18—N7—H7115.9 (17)
C1—N2—C2125.29 (18)O13—N8—O14124.30 (19)
C1—N2—H2118.9 (16)O13—N8—C26118.52 (17)
C2—N2—H2115.6 (16)O14—N8—C26117.12 (18)
O4—N3—O5124.6 (2)O16'—N9—O1657.1 (8)
O4—N3—C10118.05 (19)O16'—N9—O1581.8 (10)
O5—N3—C10117.3 (2)O16—N9—O15121.3 (4)
O6—N4—O7122.9 (2)O16'—N9—O15'115.5 (8)
O6—N4—C8118.8 (2)O16—N9—O15'67.1 (7)
O7—N4—C8117.6 (2)O15—N9—O15'103.5 (7)
C12—N5—C13114.51 (18)O16'—N9—C24125.0 (6)
C12—N5—C15110.22 (18)O16—N9—C24121.6 (4)
C13—N5—C15113.58 (18)O15—N9—C24116.0 (3)
C12—N5—H5105.9O15'—N9—C24110.0 (4)
C13—N5—H5105.9C28—N10—C29115.2 (2)
C15—N5—H5105.9C28—N10—C31110.8 (2)
C11—O8—H8109.5C29—N10—C31108.0 (2)
H9A—O9—H9B111.6 (17)C28—N10—H10107.5
O10—C17—N6122.98 (19)C29—N10—H10107.5
O10—C17—N7122.42 (19)C31—N10—H10107.5
N6—C17—N7114.59 (18)C27—O17—H17109.5
O3—C2—C3—C4179.2 (2)O12—C18—C19—C212.3 (3)
N2—C2—C3—C41.3 (3)N7—C18—C19—C21178.60 (18)
O3—C2—C3—C53.0 (3)C18—C19—C20—O11180.0 (2)
N2—C2—C3—C5179.08 (18)C21—C19—C20—O110.5 (3)
C2—C3—C4—O2179.2 (2)C18—C19—C20—N62.7 (3)
C5—C3—C4—O21.5 (3)C21—C19—C20—N6177.79 (18)
C2—C3—C4—N10.4 (3)C18—C19—C21—C2643.5 (3)
C5—C3—C4—N1177.35 (18)C20—C19—C21—C26137.0 (2)
C2—C3—C5—C10136.1 (2)C18—C19—C21—C22135.7 (2)
C4—C3—C5—C1046.2 (3)C20—C19—C21—C2243.7 (3)
C2—C3—C5—C645.7 (3)C26—C21—C22—C232.8 (3)
C4—C3—C5—C6132.0 (2)C19—C21—C22—C23177.86 (19)
C10—C5—C6—C72.7 (3)C21—C22—C23—C242.1 (3)
C3—C5—C6—C7178.89 (18)C21—C22—C23—Cl2178.70 (16)
C5—C6—C7—C82.8 (3)C22—C23—C24—C250.6 (3)
C5—C6—C7—Cl1178.12 (15)Cl2—C23—C24—C25178.48 (18)
C6—C7—C8—C90.2 (3)C22—C23—C24—N9178.1 (3)
Cl1—C7—C8—C9179.13 (17)Cl2—C23—C24—N92.8 (3)
C6—C7—C8—N4178.0 (2)C23—C24—C25—C262.5 (3)
Cl1—C7—C8—N43.1 (3)N9—C24—C25—C26176.3 (2)
C7—C8—C9—C102.5 (3)C24—C25—C26—C211.7 (3)
N4—C8—C9—C10175.5 (2)C24—C25—C26—N8175.07 (19)
C8—C9—C10—C52.6 (3)C22—C21—C26—C250.9 (3)
C8—C9—C10—N3172.2 (2)C19—C21—C26—C25179.86 (19)
C6—C5—C10—C90.0 (3)C22—C21—C26—N8177.43 (17)
C3—C5—C10—C9178.3 (2)C19—C21—C26—N83.3 (3)
C6—C5—C10—N3174.38 (18)O17—C27—C28—N1068.8 (4)
C3—C5—C10—N37.3 (3)O10—C17—N6—C20178.8 (2)
O8—C11—C12—N551.5 (3)N7—C17—N6—C202.0 (3)
O1—C1—N1—C4179.6 (2)O11—C20—N6—C17178.2 (2)
N2—C1—N1—C40.8 (3)C19—C20—N6—C170.7 (3)
O2—C4—N1—C1179.5 (2)O10—C17—N7—C18177.9 (2)
C3—C4—N1—C11.6 (3)N6—C17—N7—C183.0 (3)
O1—C1—N2—C2178.4 (2)O12—C18—N7—C17179.7 (2)
N1—C1—N2—C21.2 (3)C19—C18—N7—C171.1 (3)
O3—C2—N2—C1179.7 (2)C25—C26—N8—O13134.9 (2)
C3—C2—N2—C12.2 (3)C21—C26—N8—O1342.0 (3)
C9—C10—N3—O4135.0 (2)C25—C26—N8—O1442.5 (2)
C5—C10—N3—O439.9 (3)C21—C26—N8—O14140.6 (2)
C9—C10—N3—O542.1 (3)C25—C24—N9—O16'29.0 (14)
C5—C10—N3—O5143.1 (2)C23—C24—N9—O16'149.7 (13)
C9—C8—N4—O625.7 (4)C25—C24—N9—O1640.6 (8)
C7—C8—N4—O6156.4 (3)C23—C24—N9—O16140.7 (8)
C9—C8—N4—O7144.8 (3)C25—C24—N9—O15127.6 (4)
C7—C8—N4—O733.1 (4)C23—C24—N9—O1551.2 (5)
C11—C12—N5—C1358.8 (3)C25—C24—N9—O15'115.3 (8)
C11—C12—N5—C15171.7 (2)C23—C24—N9—O15'65.9 (8)
C14—C13—N5—C1266.5 (3)C27—C28—N10—C29106.6 (3)
C14—C13—N5—C1561.3 (3)C27—C28—N10—C31130.3 (3)
C16—C15—N5—C12172.3 (2)C30—C29—N10—C2862.9 (3)
C16—C15—N5—C1357.7 (3)C30—C29—N10—C31172.6 (3)
O12—C18—C19—C20177.21 (19)C32—C31—N10—C2871.2 (3)
N7—C18—C19—C201.9 (3)C32—C31—N10—C29161.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5···O9i0.911.852.749 (2)167
O8—H8···O1ii0.821.982.674 (2)141
O9—H9A···O20.84 (1)1.85 (1)2.691 (2)171 (3)
O9—H9B···O100.85 (1)2.11 (2)2.850 (2)146 (3)
N2—H2···O3ii0.85 (3)1.99 (3)2.826 (2)168 (2)
N1—H1···O100.84 (2)2.10 (2)2.933 (2)171 (2)
N10—H10···O120.911.852.698 (2)154
O17—H17···O8iii0.821.912.667 (2)153
N7—H7···O170.84 (3)2.07 (3)2.911 (2)176 (2)
N6—H6A···O10.81 (2)2.16 (2)2.947 (2)167 (2)
Symmetry codes: (i) x1, y, z; (ii) x+1, y+1, z; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC6H16NO+·C10H4ClN4O7·0.5H2O
Mr454.83
Crystal system, space groupTriclinic, P1
Temperature (K)294
a, b, c (Å)12.3775 (7), 12.8109 (8), 13.5834 (9)
α, β, γ (°)101.497 (4), 99.142 (3), 99.718 (3)
V3)2038.6 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.25
Crystal size (mm)0.30 × 0.25 × 0.20
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2004)
Tmin, Tmax0.901, 0.942
No. of measured, independent and
observed [I > 2σ(I)] reflections
36654, 7179, 5639
Rint0.031
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.138, 1.07
No. of reflections7179
No. of parameters598
No. of restraints4
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.72, 0.32

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5···O9i0.911.852.749 (2)167.0
O8—H8···O1ii0.821.982.674 (2)141.3
O9—H9A···O20.844 (10)1.854 (11)2.691 (2)171 (3)
O9—H9B···O100.847 (10)2.11 (2)2.850 (2)146 (3)
N2—H2···O3ii0.85 (3)1.99 (3)2.826 (2)168 (2)
N1—H1···O100.84 (2)2.10 (2)2.933 (2)171 (2)
N10—H10···O120.911.852.698 (2)154.2
O17—H17···O8iii0.821.912.667 (2)152.5
N7—H7···O170.84 (3)2.07 (3)2.911 (2)176 (2)
N6—H6A···O10.81 (2)2.16 (2)2.947 (2)167 (2)
Symmetry codes: (i) x1, y, z; (ii) x+1, y+1, z; (iii) x+1, y, z.
 

Acknowledgements

The authors are grateful to the SAIF, IIT, Madras, for the data collection.

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