Lamotriginium benzoate dimethyl­formamide solvate

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.

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

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

Crystal data

C9H8N5Cl2^+·C7H5O2^−·C3H7NO	Z = 2
Mr = 451.31	F(000) = 468
Triclinic, P1	Dx = 1.393 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9585 (13) Å	Cell parameters from 2930 reflections
b = 10.5522 (15) Å	θ = 2.4–23.5°
c = 12.3183 (18) Å	µ = 0.34 mm^−1
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) Å^3

Data collection

Bruker SMART CCD area detector diffractometer	2817 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
Graphite monochromator	θmax = 25.0°, θmin = 1.7°
ω scans	h = −10→10
10413 measured reflections	k = −12→12
3788 independent reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.081	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.245	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.1386P)^2 + 0.6793P] where P = (Fo^2 + 2Fc^2)/3
3788 reflections	(Δ/σ)max < 0.001
312 parameters	Δρmax = 1.05 e Å^−3
72 restraints	Δρmin = −0.51 e Å^−3

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.0797 (2)	0.57691 (13)	0.86054 (10)	0.0979 (5)
Cl2	0.0734 (2)	0.71319 (17)	1.07007 (10)	0.1178 (6)
N1	0.2805 (3)	0.5793 (3)	0.4988 (2)	0.0568 (8)
N2	0.0132 (3)	0.7095 (3)	0.5126 (3)	0.0574 (8)
H2	−0.0751	0.7338	0.4863	0.069*
N3	0.0232 (3)	0.7621 (3)	0.6010 (3)	0.0601 (8)
N4	0.4298 (4)	0.5954 (3)	0.6219 (3)	0.0713 (10)
H4A	0.5103	0.5393	0.5893	0.086*
H4B	0.4392	0.6282	0.6783	0.086*
N5	0.1175 (4)	0.5708 (3)	0.3787 (3)	0.0693 (9)
H5A	0.1949	0.5131	0.3451	0.083*
H5B	0.0261	0.5969	0.3567	0.083*
C1	0.1649 (4)	0.7864 (4)	0.7377 (3)	0.0598 (9)
C2	0.1279 (5)	0.7246 (4)	0.8431 (3)	0.0642 (10)
C3	0.1306 (5)	0.7831 (5)	0.9369 (4)	0.0719 (11)
C4	0.1731 (5)	0.8990 (5)	0.9216 (4)	0.0768 (12)
H4	0.1779	0.9362	0.9832	0.092*
C5	0.2087 (7)	0.9607 (5)	0.8167 (4)	0.0920 (15)
H5	0.2356	1.0405	0.8098	0.110*
C6	0.2075 (5)	0.9113 (4)	0.7177 (4)	0.0724 (11)
H6	0.2317	0.9547	0.6466	0.087*
C7	0.1566 (4)	0.7256 (4)	0.6384 (3)	0.0560 (9)
C8	0.2945 (4)	0.6303 (3)	0.5861 (3)	0.0537 (8)
C9	0.1391 (4)	0.6194 (3)	0.4642 (3)	0.0523 (8)
O1	−0.2673 (3)	0.7977 (3)	0.4576 (3)	0.0799 (9)
O2	−0.1842 (3)	0.6769 (3)	0.3167 (3)	0.0836 (9)
C10	−0.4554 (4)	0.7961 (4)	0.3498 (3)	0.0559 (9)
C11	−0.5760 (5)	0.8878 (4)	0.4060 (4)	0.0660 (10)
H11	−0.5551	0.9246	0.4625	0.079*
C12	−0.7276 (5)	0.9258 (5)	0.3798 (4)	0.0805 (13)
H12	−0.8075	0.9895	0.4175	0.097*
C13	−0.7614 (6)	0.8710 (5)	0.2991 (4)	0.0854 (14)
H13	−0.8643	0.8968	0.2822	0.103*
C14	−0.6441 (6)	0.7781 (6)	0.2431 (4)	0.0850 (13)
H14	−0.6678	0.7400	0.1887	0.102*
C15	−0.4919 (5)	0.7407 (4)	0.2664 (3)	0.0701 (11)
H15	−0.4125	0.6785	0.2269	0.084*
C16	−0.2895 (4)	0.7520 (4)	0.3744 (3)	0.0594 (9)
N33	0.3650 (5)	0.2619 (4)	0.1173 (3)	0.0913 (12)
O11	0.3649 (8)	0.3830 (7)	0.2416 (6)	0.123 (3)	0.729 (11)
C32	0.3337 (15)	0.2811 (9)	0.2257 (4)	0.117 (3)	0.729 (11)
H32	0.2930	0.2243	0.2826	0.140*	0.729 (11)
C34	0.4157 (16)	0.3528 (10)	0.0242 (7)	0.156 (4)	0.729 (11)
H34A	0.4450	0.4195	0.0520	0.234*	0.729 (11)
H34B	0.3301	0.3960	−0.0183	0.234*	0.729 (11)
H34C	0.5053	0.3029	−0.0226	0.234*	0.729 (11)
C35	0.345 (3)	0.1437 (12)	0.0845 (16)	0.171 (7)	0.729 (11)
H35A	0.3446	0.0760	0.1482	0.257*	0.729 (11)
H35B	0.4312	0.1096	0.0277	0.257*	0.729 (11)
H35C	0.2464	0.1672	0.0559	0.257*	0.729 (11)
O11A	0.447 (3)	0.4426 (14)	0.1648 (14)	0.120 (7)	0.271 (11)
C32A	0.414 (3)	0.3732 (13)	0.1064 (16)	0.103 (6)	0.271 (11)
H32A	0.4257	0.4099	0.0317	0.123*	0.271 (11)
C34A	0.375 (3)	0.214 (3)	0.2345 (6)	0.107 (7)	0.271 (11)
H34D	0.3900	0.2821	0.2695	0.160*	0.271 (11)
H34E	0.4625	0.1342	0.2413	0.160*	0.271 (11)
H34F	0.2780	0.1935	0.2701	0.160*	0.271 (11)
C35A	0.313 (5)	0.204 (3)	0.038 (3)	0.125 (10)	0.271 (11)
H35D	0.1999	0.2214	0.0538	0.188*	0.271 (11)
H35E	0.3626	0.1086	0.0455	0.188*	0.271 (11)
H35F	0.3429	0.2435	−0.0361	0.188*	0.271 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.1570 (13)	0.0848 (8)	0.0729 (8)	−0.0622 (8)	−0.0231 (7)	−0.0073 (6)
Cl2	0.1913 (17)	0.1291 (12)	0.0595 (7)	−0.0815 (12)	−0.0226 (8)	−0.0112 (7)
N1	0.0538 (17)	0.0552 (17)	0.0561 (17)	−0.0013 (13)	−0.0067 (13)	−0.0207 (14)
N2	0.0449 (15)	0.0635 (18)	0.0649 (18)	−0.0072 (13)	−0.0085 (13)	−0.0255 (15)
N3	0.0482 (16)	0.0687 (19)	0.0628 (18)	−0.0062 (14)	−0.0043 (14)	−0.0297 (15)
N4	0.0556 (18)	0.081 (2)	0.071 (2)	0.0123 (16)	−0.0178 (15)	−0.0386 (17)
N5	0.0604 (18)	0.076 (2)	0.074 (2)	−0.0072 (16)	−0.0091 (16)	−0.0379 (17)
C1	0.0470 (18)	0.063 (2)	0.063 (2)	−0.0022 (16)	−0.0041 (16)	−0.0207 (18)
C2	0.062 (2)	0.060 (2)	0.070 (3)	−0.0114 (17)	−0.0133 (18)	−0.0159 (18)
C3	0.070 (2)	0.078 (3)	0.073 (3)	−0.018 (2)	−0.015 (2)	−0.025 (2)
C4	0.080 (3)	0.086 (3)	0.069 (3)	−0.025 (2)	−0.003 (2)	−0.028 (2)
C5	0.113 (4)	0.081 (3)	0.093 (4)	−0.045 (3)	0.006 (3)	−0.031 (3)
C6	0.072 (2)	0.063 (2)	0.092 (3)	−0.0201 (19)	−0.004 (2)	−0.043 (2)
C7	0.051 (2)	0.057 (2)	0.056 (2)	−0.0039 (16)	−0.0076 (16)	−0.0203 (16)
C8	0.0502 (19)	0.0517 (19)	0.0520 (19)	−0.0014 (15)	−0.0058 (15)	−0.0141 (15)
C9	0.0528 (19)	0.0485 (18)	0.056 (2)	−0.0117 (15)	−0.0036 (15)	−0.0167 (15)
O1	0.0615 (16)	0.099 (2)	0.087 (2)	−0.0077 (14)	−0.0208 (14)	−0.0463 (17)
O2	0.0622 (16)	0.116 (2)	0.0779 (19)	−0.0145 (16)	−0.0072 (14)	−0.0485 (18)
C10	0.062 (2)	0.055 (2)	0.052 (2)	−0.0182 (16)	−0.0096 (16)	−0.0075 (16)
C11	0.066 (2)	0.060 (2)	0.075 (3)	−0.0160 (18)	−0.0134 (19)	−0.0180 (19)
C12	0.064 (3)	0.071 (3)	0.096 (3)	−0.005 (2)	−0.011 (2)	−0.011 (2)
C13	0.068 (3)	0.096 (3)	0.091 (3)	−0.019 (3)	−0.032 (2)	0.003 (3)
C14	0.088 (3)	0.109 (4)	0.072 (3)	−0.035 (3)	−0.031 (2)	−0.017 (3)
C15	0.073 (2)	0.080 (3)	0.062 (2)	−0.019 (2)	−0.0158 (19)	−0.019 (2)
C16	0.058 (2)	0.066 (2)	0.057 (2)	−0.0178 (18)	−0.0064 (17)	−0.0155 (17)
N33	0.087 (3)	0.088 (3)	0.099 (3)	−0.024 (2)	0.004 (2)	−0.032 (2)
O11	0.126 (5)	0.132 (5)	0.124 (6)	−0.001 (4)	−0.046 (4)	−0.079 (5)
C32	0.121 (9)	0.110 (8)	0.111 (5)	−0.014 (7)	0.001 (5)	−0.047 (5)
C34	0.216 (13)	0.173 (10)	0.083 (6)	−0.067 (9)	−0.005 (7)	−0.024 (6)
C35	0.213 (16)	0.146 (12)	0.185 (15)	−0.053 (12)	−0.044 (12)	−0.078 (10)
O11A	0.191 (18)	0.093 (10)	0.101 (12)	−0.062 (10)	−0.065 (12)	0.007 (8)
C32A	0.105 (13)	0.110 (12)	0.109 (15)	−0.033 (10)	−0.041 (12)	−0.026 (9)
C34A	0.098 (17)	0.115 (18)	0.108 (9)	−0.020 (16)	0.015 (11)	−0.067 (9)
C35A	0.14 (2)	0.12 (2)	0.127 (19)	−0.027 (19)	−0.003 (18)	−0.079 (18)

Geometric parameters (Å, º)

Cl1—C2	1.709 (4)	C11—H11	0.9300
Cl2—C3	1.721 (5)	C12—C13	1.361 (7)
N1—C8	1.330 (4)	C12—H12	0.9300
N1—C9	1.333 (5)	C13—C14	1.365 (7)
N2—N3	1.340 (4)	C13—H13	0.9300
N2—C9	1.345 (4)	C14—C15	1.369 (6)
N2—H2	0.8600	C14—H14	0.9300
N3—C7	1.286 (5)	C15—H15	0.9300
N4—C8	1.293 (5)	N33—C32	1.3488 (11)
N4—H4A	0.8600	N33—C32A	1.3501 (11)
N4—H4B	0.8600	N33—C34	1.4499 (10)
N5—C9	1.323 (5)	N33—C35A	1.4499 (10)
N5—H5A	0.8600	N33—C34A	1.4500 (11)
N5—H5B	0.8600	N33—C35	1.4500 (11)
C1—C2	1.370 (6)	O11—C32	1.2497 (11)
C1—C6	1.449 (6)	C32—H32	0.9300
C1—C7	1.505 (5)	C34—H34A	0.9600
C2—C3	1.414 (6)	C34—H34B	0.9600
C3—C4	1.361 (6)	C34—H34C	0.9600
C4—C5	1.361 (7)	C35—H35A	0.9600
C4—H4	0.9300	C35—H35B	0.9600
C5—C6	1.416 (6)	C35—H35C	0.9600
C5—H5	0.9300	O11A—C32A	1.2499 (10)
C6—H6	0.9300	C32A—H32A	0.9300
C7—C8	1.451 (5)	C34A—H34D	0.9600
O1—C16	1.282 (4)	C34A—H34E	0.9600
O2—C16	1.225 (4)	C34A—H34F	0.9600
C10—C11	1.373 (5)	C35A—H35D	0.9600
C10—C15	1.405 (5)	C35A—H35E	0.9600
C10—C16	1.487 (5)	C35A—H35F	0.9600
C11—C12	1.376 (6)
C8—N1—C9	117.5 (3)	C14—C13—H13	120.1
N3—N2—C9	121.0 (3)	C13—C14—C15	120.6 (4)
N3—N2—H2	119.5	C13—C14—H14	119.7
C9—N2—H2	119.5	C15—C14—H14	119.7
C7—N3—N2	118.6 (3)	C14—C15—C10	120.2 (4)
C8—N4—H4A	120.0	C14—C15—H15	119.9
C8—N4—H4B	120.0	C10—C15—H15	119.9
H4A—N4—H4B	120.0	O2—C16—O1	124.1 (3)
C9—N5—H5A	120.0	O2—C16—C10	120.2 (3)
C9—N5—H5B	120.0	O1—C16—C10	115.7 (3)
H5A—N5—H5B	120.0	C32—N33—C32A	81.6 (9)
C2—C1—C6	122.4 (4)	C32—N33—C34	125.9 (6)
C2—C1—C7	119.3 (4)	C32A—N33—C34	44.7 (8)
C6—C1—C7	118.3 (4)	C32—N33—C35A	140.9 (18)
C1—C2—C3	119.7 (4)	C32A—N33—C35A	131.9 (17)
C1—C2—Cl1	119.9 (3)	C34—N33—C35A	88.2 (16)
C3—C2—Cl1	120.4 (3)	C32—N33—C34A	28.2 (9)
C4—C3—C2	119.6 (4)	C32A—N33—C34A	100.1 (14)
C4—C3—Cl2	119.6 (3)	C34—N33—C34A	143.0 (13)
C2—C3—Cl2	120.7 (3)	C35A—N33—C34A	128.0 (19)
C5—C4—C3	120.5 (4)	C32—N33—C35	120.3 (9)
C5—C4—H4	119.7	C32A—N33—C35	157.5 (12)
C3—C4—H4	119.7	C34—N33—C35	113.8 (10)
C4—C5—C6	124.2 (4)	C35A—N33—C35	31.7 (15)
C4—C5—H5	117.9	C34A—N33—C35	98.8 (13)
C6—C5—H5	117.9	O11—C32—N33	112.9 (5)
C5—C6—C1	113.5 (4)	O11—C32—H32	123.5
C5—C6—H6	123.2	N33—C32—H32	123.5
C1—C6—H6	123.2	N33—C34—H34A	109.5
N3—C7—C8	121.2 (3)	N33—C34—H34B	109.5
N3—C7—C1	117.5 (3)	N33—C34—H34C	109.5
C8—C7—C1	121.3 (3)	N33—C35—H35A	109.5
N4—C8—N1	119.7 (3)	N33—C35—H35B	109.5
N4—C8—C7	121.4 (3)	N33—C35—H35C	109.5
N1—C8—C7	118.8 (3)	O11A—C32A—N33	140.1 (17)
N5—C9—N1	120.3 (3)	O11A—C32A—H32A	109.9
N5—C9—N2	116.9 (3)	N33—C32A—H32A	109.9
N1—C9—N2	122.8 (3)	N33—C34A—H34D	109.5
C11—C10—C15	118.1 (4)	N33—C34A—H34E	109.5
C11—C10—C16	122.9 (3)	H34D—C34A—H34E	109.5
C15—C10—C16	119.0 (3)	N33—C34A—H34F	109.5
C10—C11—C12	120.7 (4)	H34D—C34A—H34F	109.5
C10—C11—H11	119.6	H34E—C34A—H34F	109.5
C12—C11—H11	119.6	N33—C35A—H35D	109.5
C13—C12—C11	120.6 (4)	N33—C35A—H35E	109.5
C13—C12—H12	119.7	H35D—C35A—H35E	109.5
C11—C12—H12	119.7	N33—C35A—H35F	109.5
C12—C13—C14	119.9 (4)	H35D—C35A—H35F	109.5
C12—C13—H13	120.1	H35E—C35A—H35F	109.5
C9—N2—N3—C7	0.7 (5)	C8—N1—C9—N5	−179.1 (3)
C6—C1—C2—C3	0.1 (6)	C8—N1—C9—N2	1.1 (5)
C7—C1—C2—C3	−178.1 (3)	N3—N2—C9—N5	178.7 (3)
C6—C1—C2—Cl1	−179.7 (3)	N3—N2—C9—N1	−1.5 (5)
C7—C1—C2—Cl1	2.2 (5)	C15—C10—C11—C12	−1.1 (6)
C1—C2—C3—C4	−1.4 (6)	C16—C10—C11—C12	179.8 (4)
Cl1—C2—C3—C4	178.3 (3)	C10—C11—C12—C13	1.4 (7)
C1—C2—C3—Cl2	176.1 (3)	C11—C12—C13—C14	−0.4 (8)
Cl1—C2—C3—Cl2	−4.1 (5)	C12—C13—C14—C15	−0.8 (8)
C2—C3—C4—C5	1.9 (7)	C13—C14—C15—C10	1.1 (7)
Cl2—C3—C4—C5	−175.7 (4)	C11—C10—C15—C14	−0.1 (6)
C3—C4—C5—C6	−1.0 (8)	C16—C10—C15—C14	179.1 (4)
C4—C5—C6—C1	−0.3 (7)	C11—C10—C16—O2	−175.0 (4)
C2—C1—C6—C5	0.7 (6)	C15—C10—C16—O2	5.9 (6)
C7—C1—C6—C5	178.9 (4)	C11—C10—C16—O1	4.8 (6)
N2—N3—C7—C8	0.5 (6)	C15—C10—C16—O1	−174.3 (4)
N2—N3—C7—C1	179.9 (3)	C32A—N33—C32—O11	1.4 (13)
C2—C1—C7—N3	89.1 (5)	C34—N33—C32—O11	−5.5 (15)
C6—C1—C7—N3	−89.1 (4)	C35A—N33—C32—O11	−151 (2)
C2—C1—C7—C8	−91.5 (4)	C34A—N33—C32—O11	132 (4)
C6—C1—C7—C8	90.3 (4)	C35—N33—C32—O11	176.1 (12)
C9—N1—C8—N4	−179.3 (3)	C32—N33—C32A—O11A	14 (3)
C9—N1—C8—C7	0.1 (5)	C34—N33—C32A—O11A	−174 (4)
N3—C7—C8—N4	178.5 (4)	C35A—N33—C32A—O11A	172 (3)
C1—C7—C8—N4	−0.8 (6)	C34A—N33—C32A—O11A	−7 (4)
N3—C7—C8—N1	−0.9 (6)	C35—N33—C32A—O11A	−154 (3)
C1—C7—C8—N1	179.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5B···O2	0.86	1.93	2.785 (4)	172
N5—H5A···O11	0.86	2.10	2.952 (6)	171
N4—H4B···O11A^i	0.86	2.26	2.957 (13)	139
N4—H4B···O11^i	0.86	2.14	2.806 (6)	134
N4—H4A···N1^i	0.86	2.12	2.976 (4)	173
N2—H2···O1	0.86	1.72	2.572 (4)	169

Symmetry code: (i) −x+1, −y+1, −z+1.