Lamotrigine ethanol monosolvate

The main motif within the structure is a lamotrigine dimer stabilized by two ethanol mol­ecules. Here the lamotrigine dimer forms using amines in the ortho position of the triazine group.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.009 Å
• Disorder in solvent or counterion
• R factor = 0.098
• wR factor = 0.234
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.1 Note
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0095 Ang.
PLAT415_ALERT_2_C Short Inter D-H..H-X       H5B      ..H11A             2.14 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     17.311 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.357 Check
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          1 Check
PLAT975_ALERT_2_C Check Calcd Resid. Dens.  1.06A   From N1              0.58 eA-3
PLAT975_ALERT_2_C Check Calcd Resid. Dens.  0.97A   From O1              0.53 eA-3
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          5 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          5 Report
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large      59.87 Why ?
PLAT128_ALERT_4_G Alternate Setting for Input Space Group     C2/c       I2/a Note
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          1 Report
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  2  )        67% Note
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O1              35.4 Degree
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         48 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         25 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   9 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   9 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

(I)

Crystal data

C9H7Cl2N5·C2H6O	F(000) = 1248
Mr = 302.16	Dx = 1.420 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 21.2458 (15) Å	Cell parameters from 7221 reflections
b = 10.2320 (8) Å	θ = 2.2–26.4°
c = 14.8428 (11) Å	µ = 0.46 mm^−1
β = 118.808 (4)°	T = 100 K
V = 2827.3 (4) Å^3	Block, colourless
Z = 8	0.39 × 0.25 × 0.13 mm

Data collection

Bruker APEXII CCD diffractometer	2925 independent reflections
Radiation source: fine-focus sealed tube	2634 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
φ and ω scans	θmax = 26.6°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2015)	h = −26→26
Tmin = 0.602, Tmax = 0.745	k = −12→12
21376 measured reflections	l = −18→18

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.098	H-atom parameters constrained
wR(F^2) = 0.234	w = 1/[σ^2(Fo^2) + 59.8676P] where P = (Fo^2 + 2Fc^2)/3
S = 1.41	(Δ/σ)max < 0.001
2925 reflections	Δρmax = 0.62 e Å^−3
193 parameters	Δρmin = −0.87 e Å^−3
48 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The occupancies of the disordered atoms in the ethanol were refined with their sum set to equal 1. Restraints were applied to maintain sensible thermal and geometric parameters. The diffraction data showed slight splitting of some peaks but twinning could not be sensibly separated and modelled. However this may explain the large K values, slightly high second weight paramater and Fobs greater than Fcalc.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.16117 (9)	0.41684 (18)	0.10486 (12)	0.0254 (4)
Cl2	0.06655 (8)	0.37527 (18)	0.21033 (13)	0.0256 (4)
O1	0.4106 (2)	0.2925 (5)	0.4111 (3)	0.0192 (10)
H1A	0.397808	0.357810	0.371958	0.029*	0.484 (14)
H1B	0.398027	0.358121	0.372284	0.029*	0.516 (14)
N3	0.3251 (3)	0.6534 (5)	0.1015 (4)	0.0136 (10)
N4	0.2195 (3)	0.7095 (5)	0.0967 (4)	0.0145 (11)
H4A	0.208617	0.757236	0.041803	0.017*
H4B	0.189512	0.705023	0.121767	0.017*
N1	0.3666 (3)	0.5147 (6)	0.2792 (4)	0.0177 (11)
N2	0.4130 (3)	0.5288 (6)	0.2425 (4)	0.0185 (12)
N5	0.4347 (3)	0.6032 (7)	0.1152 (4)	0.0293 (15)
H5A	0.422053	0.646160	0.057650	0.035*
H5B	0.477226	0.565850	0.147585	0.035*
C6	0.2549 (3)	0.5427 (6)	0.2790 (4)	0.0144 (12)
C8	0.2808 (3)	0.6445 (6)	0.1415 (4)	0.0133 (12)
C7	0.3022 (3)	0.5648 (6)	0.2321 (4)	0.0142 (12)
C4	0.2351 (4)	0.5649 (7)	0.4253 (5)	0.0191 (13)
H4	0.251372	0.593442	0.493888	0.023*
C3	0.1697 (3)	0.5029 (7)	0.3727 (5)	0.0193 (14)
H3	0.140279	0.491009	0.404086	0.023*
C2	0.1470 (3)	0.4581 (7)	0.2738 (5)	0.0176 (13)
C9	0.3894 (3)	0.5948 (7)	0.1536 (5)	0.0189 (13)
C5	0.2772 (3)	0.5859 (7)	0.3788 (5)	0.0188 (13)
H5	0.321851	0.630185	0.415469	0.023*
C1	0.1893 (3)	0.4782 (6)	0.2273 (5)	0.0152 (12)
C10B	0.4570 (8)	0.2138 (16)	0.3909 (13)	0.024 (3)	0.484 (14)
H10A	0.435281	0.197369	0.316042	0.029*	0.484 (14)
H10B	0.464411	0.128524	0.426119	0.029*	0.484 (14)
C11B	0.5275 (8)	0.2819 (16)	0.4283 (14)	0.030 (4)	0.484 (14)
H11A	0.519935	0.365998	0.393000	0.045*	0.484 (14)
H11B	0.559689	0.227634	0.414026	0.045*	0.484 (14)
H11C	0.549146	0.296685	0.502588	0.045*	0.484 (14)
C10A	0.4866 (8)	0.2617 (17)	0.4439 (12)	0.030 (3)	0.516 (14)
H10C	0.500914	0.183860	0.489087	0.036*	0.516 (14)
H10D	0.516983	0.335764	0.484496	0.036*	0.516 (14)
C11A	0.5000 (8)	0.2356 (15)	0.3545 (12)	0.030 (3)	0.516 (14)
H11D	0.466604	0.168389	0.310075	0.045*	0.516 (14)
H11E	0.549503	0.205101	0.380438	0.045*	0.516 (14)
H11F	0.492715	0.316205	0.315082	0.045*	0.516 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0342 (9)	0.0289 (9)	0.0201 (8)	−0.0150 (7)	0.0189 (7)	−0.0098 (7)
Cl2	0.0144 (7)	0.0370 (10)	0.0260 (8)	−0.0077 (7)	0.0102 (6)	0.0040 (7)
O1	0.017 (2)	0.024 (2)	0.020 (2)	0.0066 (18)	0.0105 (18)	0.0100 (19)
N3	0.010 (2)	0.018 (3)	0.011 (2)	0.003 (2)	0.004 (2)	0.004 (2)
N4	0.011 (2)	0.020 (3)	0.012 (2)	0.005 (2)	0.006 (2)	0.007 (2)
N1	0.016 (3)	0.023 (3)	0.016 (3)	0.001 (2)	0.010 (2)	0.003 (2)
N2	0.010 (2)	0.031 (3)	0.015 (3)	0.006 (2)	0.007 (2)	0.008 (2)
N5	0.017 (3)	0.056 (4)	0.019 (3)	0.017 (3)	0.012 (2)	0.018 (3)
C6	0.015 (3)	0.016 (3)	0.013 (3)	0.005 (2)	0.008 (2)	0.004 (2)
C8	0.014 (3)	0.015 (3)	0.012 (3)	0.000 (2)	0.007 (2)	−0.001 (2)
C7	0.009 (3)	0.019 (3)	0.014 (3)	0.000 (2)	0.006 (2)	0.000 (2)
C4	0.025 (3)	0.020 (3)	0.013 (3)	0.003 (3)	0.010 (3)	0.003 (3)
C3	0.021 (3)	0.022 (3)	0.023 (3)	0.009 (3)	0.018 (3)	0.009 (3)
C2	0.014 (3)	0.021 (3)	0.019 (3)	−0.001 (3)	0.009 (3)	0.002 (3)
C9	0.015 (3)	0.027 (4)	0.017 (3)	0.008 (3)	0.010 (2)	0.008 (3)
C5	0.015 (3)	0.024 (3)	0.015 (3)	0.002 (3)	0.006 (2)	0.004 (3)
C1	0.019 (3)	0.015 (3)	0.012 (3)	0.003 (2)	0.009 (2)	0.002 (2)
C10B	0.020 (5)	0.026 (5)	0.028 (5)	0.006 (5)	0.013 (4)	0.005 (5)
C11B	0.020 (7)	0.028 (7)	0.044 (8)	0.008 (6)	0.017 (6)	0.015 (6)
C10A	0.017 (5)	0.039 (6)	0.031 (5)	0.007 (5)	0.011 (4)	0.013 (5)
C11A	0.030 (6)	0.027 (7)	0.040 (7)	0.009 (6)	0.021 (6)	0.008 (6)

Geometric parameters (Å, º)

Cl1—C1	1.735 (6)	C8—C7	1.446 (8)
Cl2—C2	1.725 (6)	C4—H4	0.9500
O1—H1A	0.8400	C4—C3	1.377 (9)
O1—H1B	0.8400	C4—C5	1.386 (9)
O1—C10B	1.413 (15)	C3—H3	0.9500
O1—C10A	1.477 (14)	C3—C2	1.384 (9)
N3—C8	1.335 (7)	C2—C1	1.387 (8)
N3—C9	1.344 (8)	C5—H5	0.9500
N4—H4A	0.8800	C10B—H10A	0.9900
N4—H4B	0.8800	C10B—H10B	0.9900
N4—C8	1.322 (8)	C10B—C11B	1.50 (2)
N1—N2	1.345 (7)	C11B—H11A	0.9800
N1—C7	1.304 (8)	C11B—H11B	0.9800
N2—C9	1.346 (8)	C11B—H11C	0.9800
N5—H5A	0.8800	C10A—H10C	0.9900
N5—H5B	0.8800	C10A—H10D	0.9900
N5—C9	1.336 (8)	C10A—C11A	1.51 (2)
C6—C7	1.490 (8)	C11A—H11D	0.9800
C6—C5	1.392 (9)	C11A—H11E	0.9800
C6—C1	1.391 (9)	C11A—H11F	0.9800
C10B—O1—H1A	109.5	N5—C9—N2	116.5 (6)
C10A—O1—H1B	109.5	C6—C5—H5	119.7
C8—N3—C9	116.9 (5)	C4—C5—C6	120.6 (6)
H4A—N4—H4B	120.0	C4—C5—H5	119.7
C8—N4—H4A	120.0	C6—C1—Cl1	119.8 (5)
C8—N4—H4B	120.0	C2—C1—Cl1	119.2 (5)
C7—N1—N2	121.7 (5)	C2—C1—C6	120.9 (6)
N1—N2—C9	116.9 (5)	O1—C10B—H10A	109.8
H5A—N5—H5B	120.0	O1—C10B—H10B	109.8
C9—N5—H5A	120.0	O1—C10B—C11B	109.3 (13)
C9—N5—H5B	120.0	H10A—C10B—H10B	108.3
C5—C6—C7	119.2 (6)	C11B—C10B—H10A	109.8
C1—C6—C7	122.4 (5)	C11B—C10B—H10B	109.8
C1—C6—C5	118.3 (6)	C10B—C11B—H11A	109.5
N3—C8—C7	118.6 (5)	C10B—C11B—H11B	109.5
N4—C8—N3	118.5 (5)	C10B—C11B—H11C	109.5
N4—C8—C7	122.9 (5)	H11A—C11B—H11B	109.5
N1—C7—C6	117.3 (5)	H11A—C11B—H11C	109.5
N1—C7—C8	119.9 (5)	H11B—C11B—H11C	109.5
C8—C7—C6	122.7 (5)	O1—C10A—H10C	109.0
C3—C4—H4	119.8	O1—C10A—H10D	109.0
C3—C4—C5	120.5 (6)	O1—C10A—C11A	112.8 (12)
C5—C4—H4	119.8	H10C—C10A—H10D	107.8
C4—C3—H3	120.2	C11A—C10A—H10C	109.0
C4—C3—C2	119.6 (6)	C11A—C10A—H10D	109.0
C2—C3—H3	120.2	C10A—C11A—H11D	109.5
C3—C2—Cl2	119.3 (5)	C10A—C11A—H11E	109.5
C3—C2—C1	120.0 (6)	C10A—C11A—H11F	109.5
C1—C2—Cl2	120.7 (5)	H11D—C11A—H11E	109.5
N3—C9—N2	125.6 (5)	H11D—C11A—H11F	109.5
N5—C9—N3	117.9 (6)	H11E—C11A—H11F	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.84	2.01	2.848 (7)	179
N4—H4A···N3^i	0.88	2.10	2.972 (7)	172
N4—H4B···O1^ii	0.88	2.14	2.841 (7)	137
N5—H5A···O1^iii	0.88	2.16	3.014 (7)	163
N5—H5B···N2^iv	0.88	2.14	2.987 (8)	161

Symmetry codes: (i) −x+1/2, −y+3/2, −z; (ii) −x+1/2, y+1/2, −z+1/2; (iii) x, −y+1, z−1/2; (iv) −x+1, y, −z+1/2.