In the title compound, C
9H
8Cl
2N
5+·H
2PO
4−·C
9H
11NO [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
R22(8) and
R32(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)°.
Supporting information
CCDC reference: 797764
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
(C-C) = 0.007 Å
- R factor = 0.068
- wR factor = 0.240
- Data-to-parameter ratio = 13.7
checkCIF/PLATON results
No syntax errors found
Alert level B
DIFMX01_ALERT_2_B The maximum difference density is > 0.1*ZMAX*1.00
_refine_diff_density_max given = 1.815
Test value = 1.700
PLAT097_ALERT_2_B Large Reported Max. (Positive) Residual Density 1.82 eA-3
Alert level C
DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75
The relevant atom site should be identified.
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.34
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.07
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang .. 7
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 79
PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings Differ ?
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 8
Alert level G
PLAT072_ALERT_2_G SHELXL First Parameter in WGHT Unusually Large. 0.13
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 8
PLAT960_ALERT_3_G Number of Intensities with I .LT. - 2*sig(I) .. 17
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
3 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
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.
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.
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium
dihydrogen phosphate–4-(dimethylamino)benzaldehyde (1/1)
top
Crystal data top
C9H8Cl2N5+·H2PO4−·C9H11NO | Z = 2 |
Mr = 503.28 | F(000) = 520 |
Triclinic, P1 | Dx = 1.488 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.1586 (4) Å | Cell parameters from 8437 reflections |
b = 10.5206 (6) Å | θ = 2.3–28.0° |
c = 13.6359 (7) Å | µ = 0.40 mm−1 |
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 top
Bruker Kappa APEXII CCD area detector diffractometer | 3219 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.031 |
Graphite monochromator | θmax = 26.0°, θmin = 1.5° |
phi and ω scans | h = −10→9 |
19715 measured reflections | k = −12→12 |
4310 independent reflections | l = −16→16 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.068 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.240 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.1269P)2 + 2.426P] where P = (Fo2 + 2Fc2)/3 |
4310 reflections | (Δ/σ)max = 0.011 |
315 parameters | Δρmax = 1.82 e Å−3 |
8 restraints | Δρmin = −0.54 e Å−3 |
Crystal data top
C9H8Cl2N5+·H2PO4−·C9H11NO | γ = 99.746 (3)° |
Mr = 503.28 | V = 1123.49 (10) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.1586 (4) Å | Mo Kα radiation |
b = 10.5206 (6) Å | µ = 0.40 mm−1 |
c = 13.6359 (7) Å | T = 296 K |
α = 98.665 (3)° | 0.31 × 0.27 × 0.25 mm |
β = 98.131 (4)° | |
Data collection top
Bruker Kappa APEXII CCD area detector diffractometer | 3219 reflections with I > 2σ(I) |
19715 measured reflections | Rint = 0.031 |
4310 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.068 | 8 restraints |
wR(F2) = 0.240 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 1.82 e Å−3 |
4310 reflections | Δρmin = −0.54 e Å−3 |
315 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 | x | y | z | Uiso*/Ueq | |
C1 | 0.1434 (6) | 0.8025 (4) | 0.0052 (3) | 0.0389 (10) | |
C2 | 0.1627 (6) | 0.8530 (4) | −0.0804 (3) | 0.0431 (10) | |
C3 | 0.0246 (7) | 0.8825 (5) | −0.1405 (4) | 0.0511 (12) | |
C4 | −0.1267 (7) | 0.8634 (5) | −0.1102 (4) | 0.0529 (13) | |
H4 | −0.2188 | 0.8840 | −0.1487 | 0.064* | |
C5 | −0.1487 (7) | 0.8146 (6) | −0.0248 (4) | 0.0577 (13) | |
H5 | −0.2550 | 0.8049 | −0.0065 | 0.069* | |
C6 | −0.0185 (6) | 0.7787 (5) | 0.0361 (5) | 0.0570 (14) | |
H6 | −0.0353 | 0.7419 | 0.0926 | 0.068* | |
C7 | 0.2925 (6) | 0.7763 (4) | 0.0699 (3) | 0.0378 (9) | |
C8 | 0.3738 (5) | 0.6668 (4) | 0.0404 (3) | 0.0372 (9) | |
C9 | 0.5728 (5) | 0.7406 (4) | 0.1818 (3) | 0.0301 (8) | |
C10 | 0.2160 (5) | 0.5795 (4) | 0.2953 (3) | 0.0366 (9) | |
C11 | 0.2531 (7) | 0.4619 (5) | 0.2513 (4) | 0.0506 (12) | |
H11 | 0.1751 | 0.4067 | 0.1995 | 0.061* | |
C12 | 0.4023 (7) | 0.4262 (5) | 0.2830 (4) | 0.0578 (14) | |
H12 | 0.4235 | 0.3466 | 0.2530 | 0.069* | |
C13 | 0.5258 (6) | 0.5084 (5) | 0.3607 (3) | 0.0421 (10) | |
C14 | 0.4861 (5) | 0.6265 (4) | 0.4056 (3) | 0.0388 (10) | |
H14 | 0.5626 | 0.6817 | 0.4581 | 0.047* | |
C15 | 0.3367 (5) | 0.6605 (4) | 0.3728 (3) | 0.0380 (9) | |
H15 | 0.3142 | 0.7397 | 0.4027 | 0.046* | |
C16 | 0.0600 (6) | 0.6187 (4) | 0.2665 (3) | 0.0416 (10) | |
H16 | 0.0468 | 0.6993 | 0.2997 | 0.050* | |
C17 | 0.8050 (7) | 0.5653 (6) | 0.4645 (5) | 0.0649 (15) | |
H17A | 0.7933 | 0.6538 | 0.4610 | 0.097* | |
H17B | 0.9142 | 0.5534 | 0.4510 | 0.097* | |
H17C | 0.7933 | 0.5480 | 0.5306 | 0.097* | |
C18 | 0.7119 (9) | 0.3496 (7) | 0.3527 (6) | 0.080 (2) | |
H18A | 0.6212 | 0.2815 | 0.3586 | 0.120* | |
H18B | 0.8149 | 0.3387 | 0.3913 | 0.120* | |
H18C | 0.7238 | 0.3447 | 0.2833 | 0.120* | |
N1 | 0.3508 (5) | 0.8558 (3) | 0.1537 (3) | 0.0387 (8) | |
N2 | 0.4890 (4) | 0.8348 (3) | 0.2110 (2) | 0.0348 (8) | |
H2 | 0.525 (7) | 0.894 (4) | 0.265 (3) | 0.062 (17)* | |
N3 | 0.5143 (4) | 0.6533 (3) | 0.0951 (2) | 0.0351 (8) | |
N4 | 0.7119 (5) | 0.7329 (4) | 0.2380 (3) | 0.0386 (8) | |
H4A | 0.752 (6) | 0.662 (3) | 0.225 (4) | 0.046* | |
H4B | 0.755 (6) | 0.784 (4) | 0.294 (2) | 0.046* | |
N5 | 0.3095 (6) | 0.5793 (4) | −0.0417 (3) | 0.0549 (12) | |
H5A | 0.358 (7) | 0.514 (4) | −0.064 (4) | 0.066* | |
H5B | 0.207 (4) | 0.574 (6) | −0.073 (4) | 0.066* | |
N6 | 0.6754 (6) | 0.4756 (4) | 0.3905 (4) | 0.0564 (11) | |
Cl1 | 0.36141 (18) | 0.88738 (17) | −0.11201 (11) | 0.0679 (5) | |
Cl2 | 0.0485 (3) | 0.9446 (2) | −0.24770 (12) | 0.0872 (6) | |
P1 | 0.73789 (13) | 0.97774 (10) | 0.46306 (8) | 0.0335 (3) | |
O1 | 0.6763 (4) | 0.9254 (4) | 0.5559 (2) | 0.0525 (9) | |
H1 | 0.600 (6) | 0.955 (6) | 0.578 (5) | 0.07 (2)* | |
O2 | 0.5893 (4) | 0.9922 (3) | 0.3893 (2) | 0.0387 (7) | |
O3 | 0.8488 (4) | 1.1173 (3) | 0.5014 (3) | 0.0515 (9) | |
H3 | 0.949 (3) | 1.122 (6) | 0.521 (5) | 0.07 (2)* | |
O4 | 0.8423 (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) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.042 (2) | 0.035 (2) | 0.036 (2) | 0.0089 (17) | −0.0034 (18) | 0.0011 (17) |
C2 | 0.043 (3) | 0.043 (2) | 0.038 (2) | 0.0045 (19) | 0.0011 (19) | −0.0010 (19) |
C3 | 0.061 (3) | 0.044 (3) | 0.042 (3) | 0.007 (2) | −0.008 (2) | 0.006 (2) |
C4 | 0.055 (3) | 0.046 (3) | 0.052 (3) | 0.013 (2) | −0.009 (2) | 0.003 (2) |
C5 | 0.043 (3) | 0.066 (3) | 0.065 (3) | 0.016 (2) | 0.005 (2) | 0.012 (3) |
C6 | 0.032 (2) | 0.060 (3) | 0.073 (4) | 0.018 (2) | −0.003 (2) | −0.005 (3) |
C7 | 0.042 (2) | 0.036 (2) | 0.032 (2) | 0.0090 (18) | −0.0045 (17) | 0.0000 (16) |
C8 | 0.038 (2) | 0.036 (2) | 0.033 (2) | 0.0109 (17) | −0.0067 (17) | −0.0009 (16) |
C9 | 0.029 (2) | 0.033 (2) | 0.0252 (18) | 0.0041 (15) | 0.0014 (15) | 0.0032 (15) |
C10 | 0.036 (2) | 0.036 (2) | 0.035 (2) | 0.0088 (17) | −0.0029 (17) | 0.0038 (17) |
C11 | 0.053 (3) | 0.041 (2) | 0.048 (3) | 0.013 (2) | −0.013 (2) | −0.005 (2) |
C12 | 0.061 (3) | 0.044 (3) | 0.064 (3) | 0.025 (2) | −0.006 (3) | −0.006 (2) |
C13 | 0.037 (2) | 0.049 (3) | 0.043 (2) | 0.0137 (19) | 0.0019 (18) | 0.012 (2) |
C14 | 0.031 (2) | 0.040 (2) | 0.041 (2) | 0.0042 (17) | −0.0025 (17) | 0.0046 (18) |
C15 | 0.037 (2) | 0.035 (2) | 0.039 (2) | 0.0071 (17) | 0.0007 (17) | 0.0016 (17) |
C16 | 0.041 (2) | 0.045 (2) | 0.037 (2) | 0.0151 (19) | −0.0046 (18) | 0.0030 (19) |
C17 | 0.041 (3) | 0.080 (4) | 0.076 (4) | 0.020 (3) | −0.007 (3) | 0.029 (3) |
C18 | 0.075 (5) | 0.080 (4) | 0.094 (5) | 0.051 (4) | 0.005 (4) | 0.015 (4) |
N1 | 0.040 (2) | 0.0405 (19) | 0.0329 (18) | 0.0127 (15) | −0.0031 (15) | 0.0026 (15) |
N2 | 0.0364 (19) | 0.0372 (19) | 0.0262 (17) | 0.0101 (15) | −0.0037 (14) | −0.0035 (14) |
N3 | 0.0362 (19) | 0.0362 (18) | 0.0286 (17) | 0.0111 (14) | −0.0045 (14) | −0.0028 (14) |
N4 | 0.036 (2) | 0.045 (2) | 0.0290 (17) | 0.0139 (16) | −0.0065 (14) | −0.0063 (15) |
N5 | 0.056 (3) | 0.049 (2) | 0.046 (2) | 0.023 (2) | −0.0238 (19) | −0.0178 (18) |
N6 | 0.049 (3) | 0.062 (3) | 0.063 (3) | 0.025 (2) | 0.001 (2) | 0.019 (2) |
Cl1 | 0.0536 (8) | 0.0924 (11) | 0.0575 (8) | 0.0018 (7) | 0.0109 (6) | 0.0257 (7) |
Cl2 | 0.0991 (13) | 0.1090 (14) | 0.0548 (9) | 0.0153 (10) | −0.0059 (8) | 0.0430 (9) |
P1 | 0.0261 (5) | 0.0405 (6) | 0.0291 (5) | 0.0093 (4) | −0.0027 (4) | −0.0049 (4) |
O1 | 0.042 (2) | 0.083 (3) | 0.0402 (18) | 0.0265 (18) | 0.0094 (15) | 0.0162 (17) |
O2 | 0.0304 (15) | 0.0498 (17) | 0.0313 (15) | 0.0123 (12) | −0.0043 (11) | −0.0031 (12) |
O3 | 0.0325 (18) | 0.0419 (18) | 0.068 (2) | 0.0122 (14) | −0.0107 (15) | −0.0153 (15) |
O4 | 0.0284 (15) | 0.0406 (16) | 0.0378 (15) | 0.0082 (12) | −0.0023 (11) | −0.0094 (12) |
O5 | 0.046 (2) | 0.060 (2) | 0.0463 (19) | 0.0173 (16) | −0.0176 (15) | −0.0037 (16) |
Geometric parameters (Å, º) top
C1—C2 | 1.371 (6) | C13—C14 | 1.409 (6) |
C1—C6 | 1.436 (7) | C14—C15 | 1.362 (6) |
C1—C7 | 1.489 (6) | C14—H14 | 0.9300 |
C2—C3 | 1.404 (7) | C15—H15 | 0.9300 |
C2—Cl1 | 1.730 (5) | C16—O5 | 1.225 (5) |
C3—C4 | 1.349 (8) | C16—H16 | 0.9300 |
C3—Cl2 | 1.711 (5) | C17—N6 | 1.449 (7) |
C4—C5 | 1.363 (8) | C17—H17A | 0.9600 |
C4—H4 | 0.9300 | C17—H17B | 0.9600 |
C5—C6 | 1.393 (7) | C17—H17C | 0.9600 |
C5—H5 | 0.9300 | C18—N6 | 1.443 (7) |
C6—H6 | 0.9300 | C18—H18A | 0.9600 |
C7—N1 | 1.286 (5) | C18—H18B | 0.9600 |
C7—C8 | 1.458 (6) | C18—H18C | 0.9600 |
C8—N5 | 1.317 (5) | N1—N2 | 1.347 (5) |
C8—N3 | 1.318 (5) | N2—H2 | 0.87 (2) |
C9—N4 | 1.298 (5) | N4—H4A | 0.87 (4) |
C9—N2 | 1.341 (5) | N4—H4B | 0.857 (19) |
C9—N3 | 1.353 (5) | N5—H5A | 0.89 (5) |
C10—C11 | 1.392 (6) | N5—H5B | 0.87 (2) |
C10—C15 | 1.401 (6) | P1—O4 | 1.496 (3) |
C10—C16 | 1.424 (6) | P1—O2 | 1.506 (3) |
C11—C12 | 1.366 (7) | P1—O3 | 1.559 (3) |
C11—H11 | 0.9300 | P1—O1 | 1.567 (4) |
C12—C13 | 1.419 (7) | O1—H1 | 0.82 (6) |
C12—H12 | 0.9300 | O3—H3 | 0.81 (2) |
C13—N6 | 1.348 (6) | | |
| | | |
C2—C1—C6 | 120.9 (4) | C13—C14—H14 | 119.7 |
C2—C1—C7 | 120.1 (4) | C14—C15—C10 | 121.9 (4) |
C6—C1—C7 | 118.9 (4) | C14—C15—H15 | 119.1 |
C1—C2—C3 | 120.9 (4) | C10—C15—H15 | 119.1 |
C1—C2—Cl1 | 119.6 (4) | O5—C16—C10 | 126.5 (4) |
C3—C2—Cl1 | 119.4 (4) | O5—C16—H16 | 116.8 |
C4—C3—C2 | 118.2 (5) | C10—C16—H16 | 116.8 |
C4—C3—Cl2 | 120.9 (4) | N6—C17—H17A | 109.5 |
C2—C3—Cl2 | 120.9 (4) | N6—C17—H17B | 109.5 |
C3—C4—C5 | 121.9 (5) | H17A—C17—H17B | 109.5 |
C3—C4—H4 | 119.0 | N6—C17—H17C | 109.5 |
C5—C4—H4 | 119.0 | H17A—C17—H17C | 109.5 |
C4—C5—C6 | 122.8 (5) | H17B—C17—H17C | 109.5 |
C4—C5—H5 | 118.6 | N6—C18—H18A | 109.5 |
C6—C5—H5 | 118.6 | N6—C18—H18B | 109.5 |
C5—C6—C1 | 115.1 (5) | H18A—C18—H18B | 109.5 |
C5—C6—H6 | 122.4 | N6—C18—H18C | 109.5 |
C1—C6—H6 | 122.4 | H18A—C18—H18C | 109.5 |
N1—C7—C8 | 120.0 (4) | H18B—C18—H18C | 109.5 |
N1—C7—C1 | 117.6 (4) | C7—N1—N2 | 117.8 (3) |
C8—C7—C1 | 122.3 (3) | C9—N2—N1 | 123.0 (3) |
N5—C8—N3 | 118.3 (4) | C9—N2—H2 | 123 (4) |
N5—C8—C7 | 121.0 (4) | N1—N2—H2 | 113 (4) |
N3—C8—C7 | 120.7 (4) | C8—N3—C9 | 117.1 (3) |
N4—C9—N2 | 119.3 (3) | C9—N4—H4A | 118 (3) |
N4—C9—N3 | 119.7 (4) | C9—N4—H4B | 124 (4) |
N2—C9—N3 | 121.1 (3) | H4A—N4—H4B | 117 (5) |
C11—C10—C15 | 118.0 (4) | C8—N5—H5A | 124 (4) |
C11—C10—C16 | 122.8 (4) | C8—N5—H5B | 121 (4) |
C15—C10—C16 | 119.2 (4) | H5A—N5—H5B | 114 (6) |
C12—C11—C10 | 121.0 (4) | C13—N6—C18 | 121.9 (5) |
C12—C11—H11 | 119.5 | C13—N6—C17 | 120.8 (4) |
C10—C11—H11 | 119.5 | C18—N6—C17 | 117.2 (5) |
C11—C12—C13 | 121.3 (4) | O4—P1—O2 | 114.31 (16) |
C11—C12—H12 | 119.4 | O4—P1—O3 | 109.93 (18) |
C13—C12—H12 | 119.4 | O2—P1—O3 | 107.15 (19) |
N6—C13—C14 | 121.1 (4) | O4—P1—O1 | 107.16 (19) |
N6—C13—C12 | 121.6 (4) | O2—P1—O1 | 110.19 (18) |
C14—C13—C12 | 117.3 (4) | O3—P1—O1 | 107.9 (2) |
C15—C14—C13 | 120.6 (4) | P1—O1—H1 | 118 (5) |
C15—C14—H14 | 119.7 | P1—O3—H3 | 118 (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—Cl1 | 177.0 (4) | C11—C12—C13—C14 | 1.6 (8) |
C7—C1—C2—Cl1 | −0.6 (6) | N6—C13—C14—C15 | 177.9 (4) |
C1—C2—C3—C4 | 1.8 (7) | C12—C13—C14—C15 | −1.8 (7) |
Cl1—C2—C3—C4 | −175.4 (4) | C13—C14—C15—C10 | 1.2 (7) |
C1—C2—C3—Cl2 | −179.6 (3) | C11—C10—C15—C14 | −0.4 (7) |
Cl1—C2—C3—Cl2 | 3.2 (6) | C16—C10—C15—C14 | 178.1 (4) |
C2—C3—C4—C5 | −1.2 (7) | C11—C10—C16—O5 | 0.5 (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—N2 | 0.9 (6) |
C4—C5—C6—C1 | 2.9 (8) | C1—C7—N1—N2 | −178.0 (4) |
C2—C1—C6—C5 | −2.1 (7) | N4—C9—N2—N1 | 174.9 (4) |
C7—C1—C6—C5 | 175.6 (4) | N3—C9—N2—N1 | −5.4 (6) |
C2—C1—C7—N1 | 105.5 (5) | C7—N1—N2—C9 | 4.1 (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—C9 | 3.7 (6) |
C6—C1—C7—C8 | 108.9 (5) | N4—C9—N3—C8 | −179.1 (4) |
N1—C7—C8—N5 | 175.3 (5) | N2—C9—N3—C8 | 1.2 (6) |
C1—C7—C8—N5 | −5.8 (7) | C14—C13—N6—C18 | 173.7 (5) |
N1—C7—C8—N3 | −4.9 (7) | C12—C13—N6—C18 | −6.7 (8) |
C1—C7—C8—N3 | 173.9 (4) | C14—C13—N6—C17 | −4.5 (7) |
C15—C10—C11—C12 | 0.3 (8) | C12—C13—N6—C17 | 175.2 (5) |
C16—C10—C11—C12 | −178.2 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.82 (6) | 1.82 (5) | 2.627 (5) | 171 (7) |
O3—H3···O4ii | 0.81 (2) | 1.80 (2) | 2.602 (4) | 169 (7) |
N4—H4A···O5iii | 0.87 (4) | 2.08 (3) | 2.888 (5) | 155 (5) |
N4—H4B···O4 | 0.86 (2) | 1.86 (2) | 2.719 (4) | 177 (5) |
N5—H5A···N3iv | 0.89 (5) | 2.21 (5) | 3.088 (5) | 171 (6) |
N5—H5B···O5v | 0.87 (2) | 2.14 (5) | 2.799 (5) | 132 (5) |
N2—H2···O2 | 0.87 (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. |
Experimental details
Crystal data |
Chemical formula | C9H8Cl2N5+·H2PO4−·C9H11NO |
Mr | 503.28 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 8.1586 (4), 10.5206 (6), 13.6359 (7) |
α, β, γ (°) | 98.665 (3), 98.131 (4), 99.746 (3) |
V (Å3) | 1123.49 (10) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.40 |
Crystal size (mm) | 0.31 × 0.27 × 0.25 |
|
Data collection |
Diffractometer | Bruker Kappa APEXII CCD area detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19715, 4310, 3219 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.617 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.068, 0.240, 1.07 |
No. of reflections | 4310 |
No. of parameters | 315 |
No. of restraints | 8 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 1.82, −0.54 |
Selected geometric parameters (Å, º) topC7—N1 | 1.286 (5) | P1—O2 | 1.506 (3) |
C16—O5 | 1.225 (5) | P1—O3 | 1.559 (3) |
P1—O4 | 1.496 (3) | P1—O1 | 1.567 (4) |
| | | |
O4—P1—O2 | 114.31 (16) | O4—P1—O1 | 107.16 (19) |
O4—P1—O3 | 109.93 (18) | O2—P1—O1 | 110.19 (18) |
O2—P1—O3 | 107.15 (19) | O3—P1—O1 | 107.9 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.82 (6) | 1.82 (5) | 2.627 (5) | 171 (7) |
O3—H3···O4ii | 0.81 (2) | 1.80 (2) | 2.602 (4) | 169 (7) |
N4—H4A···O5iii | 0.87 (4) | 2.08 (3) | 2.888 (5) | 155 (5) |
N4—H4B···O4 | 0.857 (19) | 1.86 (2) | 2.719 (4) | 177 (5) |
N5—H5A···N3iv | 0.89 (5) | 2.21 (5) | 3.088 (5) | 171 (6) |
N5—H5B···O5v | 0.87 (2) | 2.14 (5) | 2.799 (5) | 132 (5) |
N2—H2···O2 | 0.87 (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. |
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).