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Lamotriginium benzoate dimethyl­formamide solvate [sys­tematic name: 3,5-diamino-6-(2,3-dichloro­phen­yl)-1,2,4-tri­azin-2-ium benzoate dimethyl­formamide solvate], C9H8Cl2N5+·C7H5O2·C3H7NO, is protonated on the triazine ring. The dihedral angle between the dichlorobenzene and triazine rings is 89.6 (1)°. The dimethyl­formamide solvent molecule is disordered over two sites. N—H...O and N—H...N hydrogen bonding stabilizes the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805033428/bt6748sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805033428/bt6748Isup2.hkl
Contains datablock I

CCDC reference: 289646

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.006 Å
  • Disorder in solvent or counterion
  • R factor = 0.081
  • wR factor = 0.245
  • Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.07 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C5 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N33 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 22.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 44.70 Deg. C32A -N33 -C34 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 28.20 Deg. C32 -N33 -C34A 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 31.70 Deg. C35A -N33 -C35 1.555 1.555 1.555 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 C7 H5 O2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium benzoate dimethylformamide solvate top
Crystal data top
C9H8N5Cl2+·C7H5O2·C3H7NOZ = 2
Mr = 451.31F(000) = 468
Triclinic, P1Dx = 1.393 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.9585 (13) ÅCell parameters from 2930 reflections
b = 10.5522 (15) Åθ = 2.4–23.5°
c = 12.3183 (18) ŵ = 0.34 mm1
α = 79.442 (2)°T = 273 K
β = 78.703 (2)°Needle, colorless
γ = 71.864 (2)°0.19 × 0.11 × 0.09 mm
V = 1075.8 (3) Å3
Data collection top
Bruker SMART CCD area detector
diffractometer
2817 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
Graphite monochromatorθmax = 25.0°, θmin = 1.7°
ω scansh = 1010
10413 measured reflectionsk = 1212
3788 independent reflectionsl = 1414
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)] = 0.081Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.245H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.1386P)2 + 0.6793P]
where P = (Fo2 + 2Fc2)/3
3788 reflections(Δ/σ)max < 0.001
312 parametersΔρmax = 1.05 e Å3
72 restraintsΔρmin = 0.51 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.0797 (2)0.57691 (13)0.86054 (10)0.0979 (5)
Cl20.0734 (2)0.71319 (17)1.07007 (10)0.1178 (6)
N10.2805 (3)0.5793 (3)0.4988 (2)0.0568 (8)
N20.0132 (3)0.7095 (3)0.5126 (3)0.0574 (8)
H20.07510.73380.48630.069*
N30.0232 (3)0.7621 (3)0.6010 (3)0.0601 (8)
N40.4298 (4)0.5954 (3)0.6219 (3)0.0713 (10)
H4A0.51030.53930.58930.086*
H4B0.43920.62820.67830.086*
N50.1175 (4)0.5708 (3)0.3787 (3)0.0693 (9)
H5A0.19490.51310.34510.083*
H5B0.02610.59690.35670.083*
C10.1649 (4)0.7864 (4)0.7377 (3)0.0598 (9)
C20.1279 (5)0.7246 (4)0.8431 (3)0.0642 (10)
C30.1306 (5)0.7831 (5)0.9369 (4)0.0719 (11)
C40.1731 (5)0.8990 (5)0.9216 (4)0.0768 (12)
H40.17790.93620.98320.092*
C50.2087 (7)0.9607 (5)0.8167 (4)0.0920 (15)
H50.23561.04050.80980.110*
C60.2075 (5)0.9113 (4)0.7177 (4)0.0724 (11)
H60.23170.95470.64660.087*
C70.1566 (4)0.7256 (4)0.6384 (3)0.0560 (9)
C80.2945 (4)0.6303 (3)0.5861 (3)0.0537 (8)
C90.1391 (4)0.6194 (3)0.4642 (3)0.0523 (8)
O10.2673 (3)0.7977 (3)0.4576 (3)0.0799 (9)
O20.1842 (3)0.6769 (3)0.3167 (3)0.0836 (9)
C100.4554 (4)0.7961 (4)0.3498 (3)0.0559 (9)
C110.5760 (5)0.8878 (4)0.4060 (4)0.0660 (10)
H110.55510.92460.46250.079*
C120.7276 (5)0.9258 (5)0.3798 (4)0.0805 (13)
H120.80750.98950.41750.097*
C130.7614 (6)0.8710 (5)0.2991 (4)0.0854 (14)
H130.86430.89680.28220.103*
C140.6441 (6)0.7781 (6)0.2431 (4)0.0850 (13)
H140.66780.74000.18870.102*
C150.4919 (5)0.7407 (4)0.2664 (3)0.0701 (11)
H150.41250.67850.22690.084*
C160.2895 (4)0.7520 (4)0.3744 (3)0.0594 (9)
N330.3650 (5)0.2619 (4)0.1173 (3)0.0913 (12)
O110.3649 (8)0.3830 (7)0.2416 (6)0.123 (3)0.729 (11)
C320.3337 (15)0.2811 (9)0.2257 (4)0.117 (3)0.729 (11)
H320.29300.22430.28260.140*0.729 (11)
C340.4157 (16)0.3528 (10)0.0242 (7)0.156 (4)0.729 (11)
H34A0.44500.41950.05200.234*0.729 (11)
H34B0.33010.39600.01830.234*0.729 (11)
H34C0.50530.30290.02260.234*0.729 (11)
C350.345 (3)0.1437 (12)0.0845 (16)0.171 (7)0.729 (11)
H35A0.34460.07600.14820.257*0.729 (11)
H35B0.43120.10960.02770.257*0.729 (11)
H35C0.24640.16720.05590.257*0.729 (11)
O11A0.447 (3)0.4426 (14)0.1648 (14)0.120 (7)0.271 (11)
C32A0.414 (3)0.3732 (13)0.1064 (16)0.103 (6)0.271 (11)
H32A0.42570.40990.03170.123*0.271 (11)
C34A0.375 (3)0.214 (3)0.2345 (6)0.107 (7)0.271 (11)
H34D0.39000.28210.26950.160*0.271 (11)
H34E0.46250.13420.24130.160*0.271 (11)
H34F0.27800.19350.27010.160*0.271 (11)
C35A0.313 (5)0.204 (3)0.038 (3)0.125 (10)0.271 (11)
H35D0.19990.22140.05380.188*0.271 (11)
H35E0.36260.10860.04550.188*0.271 (11)
H35F0.34290.24350.03610.188*0.271 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1570 (13)0.0848 (8)0.0729 (8)0.0622 (8)0.0231 (7)0.0073 (6)
Cl20.1913 (17)0.1291 (12)0.0595 (7)0.0815 (12)0.0226 (8)0.0112 (7)
N10.0538 (17)0.0552 (17)0.0561 (17)0.0013 (13)0.0067 (13)0.0207 (14)
N20.0449 (15)0.0635 (18)0.0649 (18)0.0072 (13)0.0085 (13)0.0255 (15)
N30.0482 (16)0.0687 (19)0.0628 (18)0.0062 (14)0.0043 (14)0.0297 (15)
N40.0556 (18)0.081 (2)0.071 (2)0.0123 (16)0.0178 (15)0.0386 (17)
N50.0604 (18)0.076 (2)0.074 (2)0.0072 (16)0.0091 (16)0.0379 (17)
C10.0470 (18)0.063 (2)0.063 (2)0.0022 (16)0.0041 (16)0.0207 (18)
C20.062 (2)0.060 (2)0.070 (3)0.0114 (17)0.0133 (18)0.0159 (18)
C30.070 (2)0.078 (3)0.073 (3)0.018 (2)0.015 (2)0.025 (2)
C40.080 (3)0.086 (3)0.069 (3)0.025 (2)0.003 (2)0.028 (2)
C50.113 (4)0.081 (3)0.093 (4)0.045 (3)0.006 (3)0.031 (3)
C60.072 (2)0.063 (2)0.092 (3)0.0201 (19)0.004 (2)0.043 (2)
C70.051 (2)0.057 (2)0.056 (2)0.0039 (16)0.0076 (16)0.0203 (16)
C80.0502 (19)0.0517 (19)0.0520 (19)0.0014 (15)0.0058 (15)0.0141 (15)
C90.0528 (19)0.0485 (18)0.056 (2)0.0117 (15)0.0036 (15)0.0167 (15)
O10.0615 (16)0.099 (2)0.087 (2)0.0077 (14)0.0208 (14)0.0463 (17)
O20.0622 (16)0.116 (2)0.0779 (19)0.0145 (16)0.0072 (14)0.0485 (18)
C100.062 (2)0.055 (2)0.052 (2)0.0182 (16)0.0096 (16)0.0075 (16)
C110.066 (2)0.060 (2)0.075 (3)0.0160 (18)0.0134 (19)0.0180 (19)
C120.064 (3)0.071 (3)0.096 (3)0.005 (2)0.011 (2)0.011 (2)
C130.068 (3)0.096 (3)0.091 (3)0.019 (3)0.032 (2)0.003 (3)
C140.088 (3)0.109 (4)0.072 (3)0.035 (3)0.031 (2)0.017 (3)
C150.073 (2)0.080 (3)0.062 (2)0.019 (2)0.0158 (19)0.019 (2)
C160.058 (2)0.066 (2)0.057 (2)0.0178 (18)0.0064 (17)0.0155 (17)
N330.087 (3)0.088 (3)0.099 (3)0.024 (2)0.004 (2)0.032 (2)
O110.126 (5)0.132 (5)0.124 (6)0.001 (4)0.046 (4)0.079 (5)
C320.121 (9)0.110 (8)0.111 (5)0.014 (7)0.001 (5)0.047 (5)
C340.216 (13)0.173 (10)0.083 (6)0.067 (9)0.005 (7)0.024 (6)
C350.213 (16)0.146 (12)0.185 (15)0.053 (12)0.044 (12)0.078 (10)
O11A0.191 (18)0.093 (10)0.101 (12)0.062 (10)0.065 (12)0.007 (8)
C32A0.105 (13)0.110 (12)0.109 (15)0.033 (10)0.041 (12)0.026 (9)
C34A0.098 (17)0.115 (18)0.108 (9)0.020 (16)0.015 (11)0.067 (9)
C35A0.14 (2)0.12 (2)0.127 (19)0.027 (19)0.003 (18)0.079 (18)
Geometric parameters (Å, º) top
Cl1—C21.709 (4)C11—H110.9300
Cl2—C31.721 (5)C12—C131.361 (7)
N1—C81.330 (4)C12—H120.9300
N1—C91.333 (5)C13—C141.365 (7)
N2—N31.340 (4)C13—H130.9300
N2—C91.345 (4)C14—C151.369 (6)
N2—H20.8600C14—H140.9300
N3—C71.286 (5)C15—H150.9300
N4—C81.293 (5)N33—C321.3488 (11)
N4—H4A0.8600N33—C32A1.3501 (11)
N4—H4B0.8600N33—C341.4499 (10)
N5—C91.323 (5)N33—C35A1.4499 (10)
N5—H5A0.8600N33—C34A1.4500 (11)
N5—H5B0.8600N33—C351.4500 (11)
C1—C21.370 (6)O11—C321.2497 (11)
C1—C61.449 (6)C32—H320.9300
C1—C71.505 (5)C34—H34A0.9600
C2—C31.414 (6)C34—H34B0.9600
C3—C41.361 (6)C34—H34C0.9600
C4—C51.361 (7)C35—H35A0.9600
C4—H40.9300C35—H35B0.9600
C5—C61.416 (6)C35—H35C0.9600
C5—H50.9300O11A—C32A1.2499 (10)
C6—H60.9300C32A—H32A0.9300
C7—C81.451 (5)C34A—H34D0.9600
O1—C161.282 (4)C34A—H34E0.9600
O2—C161.225 (4)C34A—H34F0.9600
C10—C111.373 (5)C35A—H35D0.9600
C10—C151.405 (5)C35A—H35E0.9600
C10—C161.487 (5)C35A—H35F0.9600
C11—C121.376 (6)
C8—N1—C9117.5 (3)C14—C13—H13120.1
N3—N2—C9121.0 (3)C13—C14—C15120.6 (4)
N3—N2—H2119.5C13—C14—H14119.7
C9—N2—H2119.5C15—C14—H14119.7
C7—N3—N2118.6 (3)C14—C15—C10120.2 (4)
C8—N4—H4A120.0C14—C15—H15119.9
C8—N4—H4B120.0C10—C15—H15119.9
H4A—N4—H4B120.0O2—C16—O1124.1 (3)
C9—N5—H5A120.0O2—C16—C10120.2 (3)
C9—N5—H5B120.0O1—C16—C10115.7 (3)
H5A—N5—H5B120.0C32—N33—C32A81.6 (9)
C2—C1—C6122.4 (4)C32—N33—C34125.9 (6)
C2—C1—C7119.3 (4)C32A—N33—C3444.7 (8)
C6—C1—C7118.3 (4)C32—N33—C35A140.9 (18)
C1—C2—C3119.7 (4)C32A—N33—C35A131.9 (17)
C1—C2—Cl1119.9 (3)C34—N33—C35A88.2 (16)
C3—C2—Cl1120.4 (3)C32—N33—C34A28.2 (9)
C4—C3—C2119.6 (4)C32A—N33—C34A100.1 (14)
C4—C3—Cl2119.6 (3)C34—N33—C34A143.0 (13)
C2—C3—Cl2120.7 (3)C35A—N33—C34A128.0 (19)
C5—C4—C3120.5 (4)C32—N33—C35120.3 (9)
C5—C4—H4119.7C32A—N33—C35157.5 (12)
C3—C4—H4119.7C34—N33—C35113.8 (10)
C4—C5—C6124.2 (4)C35A—N33—C3531.7 (15)
C4—C5—H5117.9C34A—N33—C3598.8 (13)
C6—C5—H5117.9O11—C32—N33112.9 (5)
C5—C6—C1113.5 (4)O11—C32—H32123.5
C5—C6—H6123.2N33—C32—H32123.5
C1—C6—H6123.2N33—C34—H34A109.5
N3—C7—C8121.2 (3)N33—C34—H34B109.5
N3—C7—C1117.5 (3)N33—C34—H34C109.5
C8—C7—C1121.3 (3)N33—C35—H35A109.5
N4—C8—N1119.7 (3)N33—C35—H35B109.5
N4—C8—C7121.4 (3)N33—C35—H35C109.5
N1—C8—C7118.8 (3)O11A—C32A—N33140.1 (17)
N5—C9—N1120.3 (3)O11A—C32A—H32A109.9
N5—C9—N2116.9 (3)N33—C32A—H32A109.9
N1—C9—N2122.8 (3)N33—C34A—H34D109.5
C11—C10—C15118.1 (4)N33—C34A—H34E109.5
C11—C10—C16122.9 (3)H34D—C34A—H34E109.5
C15—C10—C16119.0 (3)N33—C34A—H34F109.5
C10—C11—C12120.7 (4)H34D—C34A—H34F109.5
C10—C11—H11119.6H34E—C34A—H34F109.5
C12—C11—H11119.6N33—C35A—H35D109.5
C13—C12—C11120.6 (4)N33—C35A—H35E109.5
C13—C12—H12119.7H35D—C35A—H35E109.5
C11—C12—H12119.7N33—C35A—H35F109.5
C12—C13—C14119.9 (4)H35D—C35A—H35F109.5
C12—C13—H13120.1H35E—C35A—H35F109.5
C9—N2—N3—C70.7 (5)C8—N1—C9—N5179.1 (3)
C6—C1—C2—C30.1 (6)C8—N1—C9—N21.1 (5)
C7—C1—C2—C3178.1 (3)N3—N2—C9—N5178.7 (3)
C6—C1—C2—Cl1179.7 (3)N3—N2—C9—N11.5 (5)
C7—C1—C2—Cl12.2 (5)C15—C10—C11—C121.1 (6)
C1—C2—C3—C41.4 (6)C16—C10—C11—C12179.8 (4)
Cl1—C2—C3—C4178.3 (3)C10—C11—C12—C131.4 (7)
C1—C2—C3—Cl2176.1 (3)C11—C12—C13—C140.4 (8)
Cl1—C2—C3—Cl24.1 (5)C12—C13—C14—C150.8 (8)
C2—C3—C4—C51.9 (7)C13—C14—C15—C101.1 (7)
Cl2—C3—C4—C5175.7 (4)C11—C10—C15—C140.1 (6)
C3—C4—C5—C61.0 (8)C16—C10—C15—C14179.1 (4)
C4—C5—C6—C10.3 (7)C11—C10—C16—O2175.0 (4)
C2—C1—C6—C50.7 (6)C15—C10—C16—O25.9 (6)
C7—C1—C6—C5178.9 (4)C11—C10—C16—O14.8 (6)
N2—N3—C7—C80.5 (6)C15—C10—C16—O1174.3 (4)
N2—N3—C7—C1179.9 (3)C32A—N33—C32—O111.4 (13)
C2—C1—C7—N389.1 (5)C34—N33—C32—O115.5 (15)
C6—C1—C7—N389.1 (4)C35A—N33—C32—O11151 (2)
C2—C1—C7—C891.5 (4)C34A—N33—C32—O11132 (4)
C6—C1—C7—C890.3 (4)C35—N33—C32—O11176.1 (12)
C9—N1—C8—N4179.3 (3)C32—N33—C32A—O11A14 (3)
C9—N1—C8—C70.1 (5)C34—N33—C32A—O11A174 (4)
N3—C7—C8—N4178.5 (4)C35A—N33—C32A—O11A172 (3)
C1—C7—C8—N40.8 (6)C34A—N33—C32A—O11A7 (4)
N3—C7—C8—N10.9 (6)C35—N33—C32A—O11A154 (3)
C1—C7—C8—N1179.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5B···O20.861.932.785 (4)172
N5—H5A···O110.862.102.952 (6)171
N4—H4B···O11Ai0.862.262.957 (13)139
N4—H4B···O11i0.862.142.806 (6)134
N4—H4A···N1i0.862.122.976 (4)173
N2—H2···O10.861.722.572 (4)169
Symmetry code: (i) x+1, y+1, z+1.
 

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