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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): o2558.
Published online 2010 September 15. doi:  10.1107/S1600536810034884
PMCID: PMC2983263

Lamotriginium dihydrogen phosphate–4-(dimethyl­amino)­benzaldehyde (1/1)

Abstract

In the title compound, C9H8Cl2N5 +·H2PO4 ·C9H11NO [systematic name: 3,5-diamino-6-(2,3-dichloro­phen­yl)-1,2,4-triazin-2-ium dihydrogen phosphate–4-(dimethyl­amino)­benz­alde­hyde (1/1)], inter­molecular N—H(...)O and O—H(...)O hydrogen bonds produce R 2 2(8) and R 3 2(8) rings, generating a layer. Inter­molecular N—H(...)N inter­actions also occur. The dihedral angle between the rings in the cation is 71.73 (12)°.

Related literature

For the graph-set analysis of hydrogen-bond patterns, see: Bernstein et al. (1995 [triangle]). For related structures, see: Sridhar & Ravikumar (2006 [triangle]). For bond-valence calculations, see: Brese & O’Keeffe (1991 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2558-scheme1.jpg

Experimental

Crystal data

  • C9H8Cl2N5 +·H2PO4 ·C9H11NO
  • M r = 503.28
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2558-efi3.jpg
  • a = 8.1586 (4) Å
  • b = 10.5206 (6) Å
  • c = 13.6359 (7) Å
  • α = 98.665 (3)°
  • β = 98.131 (4)°
  • γ = 99.746 (3)°
  • V = 1123.49 (10) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.40 mm−1
  • T = 296 K
  • 0.31 × 0.27 × 0.25 mm

Data collection

  • Bruker Kappa APEXII CCD area detector diffractometer
  • 19715 measured reflections
  • 4310 independent reflections
  • 3219 reflections with I > 2σ(I)
  • R int = 0.031

Refinement

  • R[F 2 > 2σ(F 2)] = 0.068
  • wR(F 2) = 0.240
  • S = 1.07
  • 4310 reflections
  • 315 parameters
  • 8 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 1.82 e Å−3
  • Δρmin = −0.54 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2002 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810034884/jh2198sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034884/jh2198Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

IUK thanks the Higher Education Commission of Pakistan for its financial support under the project ‘Strengthening of the Materials Chemistry Laboratory’ at GCUL.

supplementary crystallographic information

Comment

The title compound is a salt of Lamotrigine (Sridhar et al., 2006) an anticonvulsant drug used in the treatment of epilepsy and bipolar disorder. Herein we report the synthesis and crystal structure of title compound (I).

The molecular structure and atom-labelling scheme are shown in Fig. 1. Selected bond distances and angles are given in Table 1. The P1—O2 and P1—O4 bond lengths [1.506 (3)Å and 1.496 (3) Å] indicate significant single-bond character, whereas the P1—O1 and P1—O3 bond lengths [1.567 (4)Å and 1.559 (3) Å] are indicative of significant double-bond character. The O—P—O angles lie in the range 107.15 (19)–114.31 (16)°. Linkages P1—O1 and P1—O3 constitute POH groups, as confirmed both by the location of H atoms in the difference Fourier maps and by bond-valence calculations (Brese & O'Keeffe, 1991).

The amino atom N5 in the molecule at (x, y, z) acts as a hydrogen-bond donor (Table 2) to atom N3iv so forming a centrosymmetric R22(8) ring (Bernstein et al., 1995) centred at (1/2, 1/2, 0). Similarly, atom O3 in the molecule at (x, y, z) acts as a hydrogen-bond donor to atom O4ii so forming a centrosymmetric R22(8) ring centred at (1, 1, 1/2). The combination of N—H···O and O—H···O hydrogen bonds generates R32(8) and R22(8) rings parallel to the [111] direction (Fig. 2).

Experimental

15 ml (0.06M) Methanolic solution of Lamotrigine is mixed with 15 ml (0.06M) Methanolic solution of 4-dimethylaminobenzaldehyde in glass beaker on hot plate stirrer for 10 minutes. Then add 3–4 drops of (85%) phosphoric acid and again mix for 4–5 h on hot plate stirrer. Yellow prisms of (I) were obtained by slow evaporation from methanol.

Refinement

All H atoms bound to C atoms were refined using a riding model, with C—H = 0.93Å and Uiso(H) = 1.2Ueq(C) for aromatic C atoms and C—H = 0.96Å and Uiso(H) = 1.5Ueq(C) for methyl C atoms. Other H atoms bound to N and O atoms were located in difference maps and refined subject to a DFIX restraint of O—H = 0.82 (2)Å and N—H = 0.87 (2) Å.

Figures

Fig. 1.
A view of one molecule of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii. Hydrogen bonds are indicated by dashed lines.
Fig. 2.
Part of the crystal structure of (I), showing the formation of a hydrogen-bonded sheet built from R22(8) and R32(8) rings. For the sake of clarity, H atoms not involved in the motif shown have been omitted.

Crystal data

C9H8Cl2N5+·H2PO4·C9H11NOZ = 2
Mr = 503.28F(000) = 520
Triclinic, P1Dx = 1.488 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.1586 (4) ÅCell parameters from 8437 reflections
b = 10.5206 (6) Åθ = 2.3–28.0°
c = 13.6359 (7) ŵ = 0.40 mm1
α = 98.665 (3)°T = 296 K
β = 98.131 (4)°Prism, yellow
γ = 99.746 (3)°0.31 × 0.27 × 0.25 mm
V = 1123.49 (10) Å3

Data collection

Bruker Kappa APEXII CCD area detector diffractometer3219 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.031
graphiteθmax = 26.0°, θmin = 1.5°
phi and ω scansh = −10→9
19715 measured reflectionsk = −12→12
4310 independent reflectionsl = −16→16

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.240H atoms treated by a mixture of independent and constrained refinement
S = 1.07w = 1/[σ2(Fo2) + (0.1269P)2 + 2.426P] where P = (Fo2 + 2Fc2)/3
4310 reflections(Δ/σ)max = 0.011
315 parametersΔρmax = 1.82 e Å3
8 restraintsΔρmin = −0.54 e Å3

Special details

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)

xyzUiso*/Ueq
C10.1434 (6)0.8025 (4)0.0052 (3)0.0389 (10)
C20.1627 (6)0.8530 (4)−0.0804 (3)0.0431 (10)
C30.0246 (7)0.8825 (5)−0.1405 (4)0.0511 (12)
C4−0.1267 (7)0.8634 (5)−0.1102 (4)0.0529 (13)
H4−0.21880.8840−0.14870.064*
C5−0.1487 (7)0.8146 (6)−0.0248 (4)0.0577 (13)
H5−0.25500.8049−0.00650.069*
C6−0.0185 (6)0.7787 (5)0.0361 (5)0.0570 (14)
H6−0.03530.74190.09260.068*
C70.2925 (6)0.7763 (4)0.0699 (3)0.0378 (9)
C80.3738 (5)0.6668 (4)0.0404 (3)0.0372 (9)
C90.5728 (5)0.7406 (4)0.1818 (3)0.0301 (8)
C100.2160 (5)0.5795 (4)0.2953 (3)0.0366 (9)
C110.2531 (7)0.4619 (5)0.2513 (4)0.0506 (12)
H110.17510.40670.19950.061*
C120.4023 (7)0.4262 (5)0.2830 (4)0.0578 (14)
H120.42350.34660.25300.069*
C130.5258 (6)0.5084 (5)0.3607 (3)0.0421 (10)
C140.4861 (5)0.6265 (4)0.4056 (3)0.0388 (10)
H140.56260.68170.45810.047*
C150.3367 (5)0.6605 (4)0.3728 (3)0.0380 (9)
H150.31420.73970.40270.046*
C160.0600 (6)0.6187 (4)0.2665 (3)0.0416 (10)
H160.04680.69930.29970.050*
C170.8050 (7)0.5653 (6)0.4645 (5)0.0649 (15)
H17A0.79330.65380.46100.097*
H17B0.91420.55340.45100.097*
H17C0.79330.54800.53060.097*
C180.7119 (9)0.3496 (7)0.3527 (6)0.080 (2)
H18A0.62120.28150.35860.120*
H18B0.81490.33870.39130.120*
H18C0.72380.34470.28330.120*
N10.3508 (5)0.8558 (3)0.1537 (3)0.0387 (8)
N20.4890 (4)0.8348 (3)0.2110 (2)0.0348 (8)
H20.525 (7)0.894 (4)0.265 (3)0.062 (17)*
N30.5143 (4)0.6533 (3)0.0951 (2)0.0351 (8)
N40.7119 (5)0.7329 (4)0.2380 (3)0.0386 (8)
H4A0.752 (6)0.662 (3)0.225 (4)0.046*
H4B0.755 (6)0.784 (4)0.294 (2)0.046*
N50.3095 (6)0.5793 (4)−0.0417 (3)0.0549 (12)
H5A0.358 (7)0.514 (4)−0.064 (4)0.066*
H5B0.207 (4)0.574 (6)−0.073 (4)0.066*
N60.6754 (6)0.4756 (4)0.3905 (4)0.0564 (11)
Cl10.36141 (18)0.88738 (17)−0.11201 (11)0.0679 (5)
Cl20.0485 (3)0.9446 (2)−0.24770 (12)0.0872 (6)
P10.73789 (13)0.97774 (10)0.46306 (8)0.0335 (3)
O10.6763 (4)0.9254 (4)0.5559 (2)0.0525 (9)
H10.600 (6)0.955 (6)0.578 (5)0.07 (2)*
O20.5893 (4)0.9922 (3)0.3893 (2)0.0387 (7)
O30.8488 (4)1.1173 (3)0.5014 (3)0.0515 (9)
H30.949 (3)1.122 (6)0.521 (5)0.07 (2)*
O40.8423 (3)0.8862 (3)0.4206 (2)0.0380 (7)
O5−0.0585 (4)0.5567 (3)0.2023 (3)0.0540 (9)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.042 (2)0.035 (2)0.036 (2)0.0089 (17)−0.0034 (18)0.0011 (17)
C20.043 (3)0.043 (2)0.038 (2)0.0045 (19)0.0011 (19)−0.0010 (19)
C30.061 (3)0.044 (3)0.042 (3)0.007 (2)−0.008 (2)0.006 (2)
C40.055 (3)0.046 (3)0.052 (3)0.013 (2)−0.009 (2)0.003 (2)
C50.043 (3)0.066 (3)0.065 (3)0.016 (2)0.005 (2)0.012 (3)
C60.032 (2)0.060 (3)0.073 (4)0.018 (2)−0.003 (2)−0.005 (3)
C70.042 (2)0.036 (2)0.032 (2)0.0090 (18)−0.0045 (17)0.0000 (16)
C80.038 (2)0.036 (2)0.033 (2)0.0109 (17)−0.0067 (17)−0.0009 (16)
C90.029 (2)0.033 (2)0.0252 (18)0.0041 (15)0.0014 (15)0.0032 (15)
C100.036 (2)0.036 (2)0.035 (2)0.0088 (17)−0.0029 (17)0.0038 (17)
C110.053 (3)0.041 (2)0.048 (3)0.013 (2)−0.013 (2)−0.005 (2)
C120.061 (3)0.044 (3)0.064 (3)0.025 (2)−0.006 (3)−0.006 (2)
C130.037 (2)0.049 (3)0.043 (2)0.0137 (19)0.0019 (18)0.012 (2)
C140.031 (2)0.040 (2)0.041 (2)0.0042 (17)−0.0025 (17)0.0046 (18)
C150.037 (2)0.035 (2)0.039 (2)0.0071 (17)0.0007 (17)0.0016 (17)
C160.041 (2)0.045 (2)0.037 (2)0.0151 (19)−0.0046 (18)0.0030 (19)
C170.041 (3)0.080 (4)0.076 (4)0.020 (3)−0.007 (3)0.029 (3)
C180.075 (5)0.080 (4)0.094 (5)0.051 (4)0.005 (4)0.015 (4)
N10.040 (2)0.0405 (19)0.0329 (18)0.0127 (15)−0.0031 (15)0.0026 (15)
N20.0364 (19)0.0372 (19)0.0262 (17)0.0101 (15)−0.0037 (14)−0.0035 (14)
N30.0362 (19)0.0362 (18)0.0286 (17)0.0111 (14)−0.0045 (14)−0.0028 (14)
N40.036 (2)0.045 (2)0.0290 (17)0.0139 (16)−0.0065 (14)−0.0063 (15)
N50.056 (3)0.049 (2)0.046 (2)0.023 (2)−0.0238 (19)−0.0178 (18)
N60.049 (3)0.062 (3)0.063 (3)0.025 (2)0.001 (2)0.019 (2)
Cl10.0536 (8)0.0924 (11)0.0575 (8)0.0018 (7)0.0109 (6)0.0257 (7)
Cl20.0991 (13)0.1090 (14)0.0548 (9)0.0153 (10)−0.0059 (8)0.0430 (9)
P10.0261 (5)0.0405 (6)0.0291 (5)0.0093 (4)−0.0027 (4)−0.0049 (4)
O10.042 (2)0.083 (3)0.0402 (18)0.0265 (18)0.0094 (15)0.0162 (17)
O20.0304 (15)0.0498 (17)0.0313 (15)0.0123 (12)−0.0043 (11)−0.0031 (12)
O30.0325 (18)0.0419 (18)0.068 (2)0.0122 (14)−0.0107 (15)−0.0153 (15)
O40.0284 (15)0.0406 (16)0.0378 (15)0.0082 (12)−0.0023 (11)−0.0094 (12)
O50.046 (2)0.060 (2)0.0463 (19)0.0173 (16)−0.0176 (15)−0.0037 (16)

Geometric parameters (Å, °)

C1—C21.371 (6)C13—C141.409 (6)
C1—C61.436 (7)C14—C151.362 (6)
C1—C71.489 (6)C14—H140.9300
C2—C31.404 (7)C15—H150.9300
C2—Cl11.730 (5)C16—O51.225 (5)
C3—C41.349 (8)C16—H160.9300
C3—Cl21.711 (5)C17—N61.449 (7)
C4—C51.363 (8)C17—H17A0.9600
C4—H40.9300C17—H17B0.9600
C5—C61.393 (7)C17—H17C0.9600
C5—H50.9300C18—N61.443 (7)
C6—H60.9300C18—H18A0.9600
C7—N11.286 (5)C18—H18B0.9600
C7—C81.458 (6)C18—H18C0.9600
C8—N51.317 (5)N1—N21.347 (5)
C8—N31.318 (5)N2—H20.87 (2)
C9—N41.298 (5)N4—H4A0.87 (4)
C9—N21.341 (5)N4—H4B0.857 (19)
C9—N31.353 (5)N5—H5A0.89 (5)
C10—C111.392 (6)N5—H5B0.87 (2)
C10—C151.401 (6)P1—O41.496 (3)
C10—C161.424 (6)P1—O21.506 (3)
C11—C121.366 (7)P1—O31.559 (3)
C11—H110.9300P1—O11.567 (4)
C12—C131.419 (7)O1—H10.82 (6)
C12—H120.9300O3—H30.81 (2)
C13—N61.348 (6)
C2—C1—C6120.9 (4)C13—C14—H14119.7
C2—C1—C7120.1 (4)C14—C15—C10121.9 (4)
C6—C1—C7118.9 (4)C14—C15—H15119.1
C1—C2—C3120.9 (4)C10—C15—H15119.1
C1—C2—Cl1119.6 (4)O5—C16—C10126.5 (4)
C3—C2—Cl1119.4 (4)O5—C16—H16116.8
C4—C3—C2118.2 (5)C10—C16—H16116.8
C4—C3—Cl2120.9 (4)N6—C17—H17A109.5
C2—C3—Cl2120.9 (4)N6—C17—H17B109.5
C3—C4—C5121.9 (5)H17A—C17—H17B109.5
C3—C4—H4119.0N6—C17—H17C109.5
C5—C4—H4119.0H17A—C17—H17C109.5
C4—C5—C6122.8 (5)H17B—C17—H17C109.5
C4—C5—H5118.6N6—C18—H18A109.5
C6—C5—H5118.6N6—C18—H18B109.5
C5—C6—C1115.1 (5)H18A—C18—H18B109.5
C5—C6—H6122.4N6—C18—H18C109.5
C1—C6—H6122.4H18A—C18—H18C109.5
N1—C7—C8120.0 (4)H18B—C18—H18C109.5
N1—C7—C1117.6 (4)C7—N1—N2117.8 (3)
C8—C7—C1122.3 (3)C9—N2—N1123.0 (3)
N5—C8—N3118.3 (4)C9—N2—H2123 (4)
N5—C8—C7121.0 (4)N1—N2—H2113 (4)
N3—C8—C7120.7 (4)C8—N3—C9117.1 (3)
N4—C9—N2119.3 (3)C9—N4—H4A118 (3)
N4—C9—N3119.7 (4)C9—N4—H4B124 (4)
N2—C9—N3121.1 (3)H4A—N4—H4B117 (5)
C11—C10—C15118.0 (4)C8—N5—H5A124 (4)
C11—C10—C16122.8 (4)C8—N5—H5B121 (4)
C15—C10—C16119.2 (4)H5A—N5—H5B114 (6)
C12—C11—C10121.0 (4)C13—N6—C18121.9 (5)
C12—C11—H11119.5C13—N6—C17120.8 (4)
C10—C11—H11119.5C18—N6—C17117.2 (5)
C11—C12—C13121.3 (4)O4—P1—O2114.31 (16)
C11—C12—H12119.4O4—P1—O3109.93 (18)
C13—C12—H12119.4O2—P1—O3107.15 (19)
N6—C13—C14121.1 (4)O4—P1—O1107.16 (19)
N6—C13—C12121.6 (4)O2—P1—O1110.19 (18)
C14—C13—C12117.3 (4)O3—P1—O1107.9 (2)
C15—C14—C13120.6 (4)P1—O1—H1118 (5)
C15—C14—H14119.7P1—O3—H3118 (5)
C6—C1—C2—C3−0.1 (7)C10—C11—C12—C13−0.9 (9)
C7—C1—C2—C3−177.8 (4)C11—C12—C13—N6−178.1 (5)
C6—C1—C2—Cl1177.0 (4)C11—C12—C13—C141.6 (8)
C7—C1—C2—Cl1−0.6 (6)N6—C13—C14—C15177.9 (4)
C1—C2—C3—C41.8 (7)C12—C13—C14—C15−1.8 (7)
Cl1—C2—C3—C4−175.4 (4)C13—C14—C15—C101.2 (7)
C1—C2—C3—Cl2−179.6 (3)C11—C10—C15—C14−0.4 (7)
Cl1—C2—C3—Cl23.2 (6)C16—C10—C15—C14178.1 (4)
C2—C3—C4—C5−1.2 (7)C11—C10—C16—O50.5 (8)
Cl2—C3—C4—C5−179.7 (4)C15—C10—C16—O5−177.9 (5)
C3—C4—C5—C6−1.3 (8)C8—C7—N1—N20.9 (6)
C4—C5—C6—C12.9 (8)C1—C7—N1—N2−178.0 (4)
C2—C1—C6—C5−2.1 (7)N4—C9—N2—N1174.9 (4)
C7—C1—C6—C5175.6 (4)N3—C9—N2—N1−5.4 (6)
C2—C1—C7—N1105.5 (5)C7—N1—N2—C94.1 (6)
C6—C1—C7—N1−72.2 (6)N5—C8—N3—C9−176.6 (4)
C2—C1—C7—C8−73.4 (6)C7—C8—N3—C93.7 (6)
C6—C1—C7—C8108.9 (5)N4—C9—N3—C8−179.1 (4)
N1—C7—C8—N5175.3 (5)N2—C9—N3—C81.2 (6)
C1—C7—C8—N5−5.8 (7)C14—C13—N6—C18173.7 (5)
N1—C7—C8—N3−4.9 (7)C12—C13—N6—C18−6.7 (8)
C1—C7—C8—N3173.9 (4)C14—C13—N6—C17−4.5 (7)
C15—C10—C11—C120.3 (8)C12—C13—N6—C17175.2 (5)
C16—C10—C11—C12−178.2 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.82 (6)1.82 (5)2.627 (5)171 (7)
O3—H3···O4ii0.81 (2)1.80 (2)2.602 (4)169 (7)
N4—H4A···O5iii0.87 (4)2.08 (3)2.888 (5)155 (5)
N4—H4B···O40.86 (2)1.86 (2)2.719 (4)177 (5)
N5—H5A···N3iv0.89 (5)2.21 (5)3.088 (5)171 (6)
N5—H5B···O5v0.87 (2)2.14 (5)2.799 (5)132 (5)
N2—H2···O20.87 (2)1.81 (2)2.663 (4)170 (6)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JH2198).

References

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