10,11-Dihydrocarbamazepine formic acid solvate. In the title compound [systematic name: 10,11-dihydro-5Hdibenz[b,f]azepine-5-carboxamide
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1 organic papers Acta Crystallographica Section E Structure Reports Online ISSN ,11-Dihydrocarbamazepine formic acid solvate Andrea Johnston, a Alastair J. Florence, a * Philippe Fernandes, a Norman Shankland a and Alan R. Kennedy b a Solid-State Research Group, Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, 27 Taylor Street, Glasgow G4 0NR, Scotland, and b WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland Correspondence alastair.florence@strath.ac.uk Key indicators Single-crystal X-ray study T = 123 K Mean (C C) = Å R factor = wr factor = Data-to-parameter ratio = 9.7 For details of how these key indicators were automatically derived from the article, see In the title compound [systematic name: 10,11-dihydro-5Hdibenz[b,f]azepine-5-carboxamide methanoic acid solvate], C 15 H 14 N 2 OCH 2 O 2, the dihydrocarbamazepine and formic acid molecules are hydrogen bonded to form an R 2 2(8) motif, which is further connected into a centrosymmetric double motif arrangement. Comment 10,11-Dihydrocarbamazepine (DHC) is a recognized impurity in carbamazepine (CBZ), a dibenzazepine drug used to control seizures (Cyr et al., 1987). DHC is known to crystallize in three polymorphic forms: monoclinic form I (Bandoli et al., 1992), orthorhombic form II (Harrison et al., 2006) and triclinic form III (Leech et al., 2007a). The title compound, (I), was produced during an automated parallel crystallization search (Florence, Johnston, Fernandes et al., 2006) on DHC as part of a wider study into the predicted and experimental structures of CBZ (Florence, Johnston, Price et al., 2006; Florence, Leech et al., 2006) and related molecules (Leech et al., 2007b). The sample was identified as a new form using multi-sample foil transmission X-ray powder diffraction analysis (Florence et al., 2003). Subsequent manual recrystallization from a saturated formic acid solution by slow evaporation at 298 K yielded samples of (I) suitable for singlecrystal diffraction (Fig. 1). Received 5 January 2007 Accepted 18 February 2007 The molecules in (I) adopt a hydrogen-bonded arrangement similar to that observed in the CBZ formic acid (1/1) solvate (Fleischman et al., 2003). Specifically, the DHC and formic acid molecules are connected via O2 H2O1 and N2 H2AO3 hydrogen bonds to form an R 2 2(8) (Etter, 1990) dimer motif (Table 1). A third hydrogen bond, N2 H2BO3 i [symmetry code: (i) x +1, y +1, z] joins adjacent dimers to form a centrosymmetric double motif arrangement (Fig. 2). # 2007 International Union of Crystallography All rights reserved Experimental DHC was used as received from Sigma Aldrich and a single-crystal sample of the title compound was obtained by slow evaporation of a saturated formic acid solution at 298 K. doi: /s Johnston et al. C 15 H 14 N 2 OCH 2 O 2 o1469
2 organic papers Figure 1 The asymmetric unit of (I), showing the atomic numbering used. Displacement ellipsoids are drawn at the 50% probability level; H atoms are shown as circles of arbitrary radius and hydrogen bonds as dashed lines. Crystal data C 15 H 14 N 2 OCH 2 O 2 M r = Triclinic, P1 a = (4) Å b = (12) Å c = (18) Å = (5) = (7) Data collection Nonius KappaCCD diffractometer Absorption correction: none 9817 measured reflections 1956 independent reflections Refinement R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections 202 parameters Table 1 Hydrogen-bond geometry (Å, ). = (7) V = (14) Å 3 Z =2 Mo K radiation = 0.09 mm 1 T = 123 (2) K mm 1260 reflections with I > 2(I) R int = max = 23.0 H atoms treated by a mixture of independent and constrained refinement max = 0.21 e Å 3 min = 0.22 e Å 3 D HA D H HA DA D HA O2 H2O (4) 1.52 (4) (3) 170 (4) N2 H2AO (3) 2.08 (3) (4) 163 (3) N2 H2BO3 i 0.89 (3) 2.13 (3) (4) 141 (2) Symmetry code: (i) x þ 1; y þ 1; z. The three H-atoms attached to N2 and O2 were located in a difference map and refined isotropically [N H = 0.88 (3) and 0.89 (3) Å; O H = 1.04 (4) Å]. All other H atoms were constrained to idealized geometries and included in the refinement using the riding-model approximation: U iso (H) = 1.2U eq (C) and C H = 0.95 or 0.99 Å. Figure 2 Plot showing the hydrogen-bonded dimer arrangement in (I) with two R 2 2(8) dimers joined in a centrosymmetric arrangement via an R 2 4(8) motif. Data collection: COLLECT (Hooft, 1988) and DENZO (Otwinowski & Minor, 1997); cell refinement: DENZO and COLLECT; data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97. The authors thank the Basic Technology programme of the UK Research Councils for funding this work under the project Control and Prediction of the Organic Solid State ( References Bandoli, G., Nicolini, M., Onagaro, A., Volpe, G. & Rubello, A. (1992). J. Chem. Crystallogr. 22, Cyr, T. D., Matsui, F., Sears, R. W., Curran, N. M. & Lovering, E. G. (1987). J. Assoc. Off. Anal. Chem. 70, Etter, M. C. (1990). Acc. Chem. Res. 23, Fleischman, S. G., Kuduva, S. S., McMahon, J. A., Moulton, B., Walsh, R. D. B., Rodriguez-Hornedo, N. & Zaworotko, M. J. (2003). Cryst. Growth Des. 3, Florence, A. J., Baumgartner, B., Weston, C., Shankland, N., Kennedy, A. R., Shankland, K. & David, W. I. F. (2003). J. Pharm. Sci. 92, Florence, A. J., Johnston, A., Fernandes, P., Shankland, N. & Shankland, K. (2006). J. Appl. Cryst. 39, Florence, A. J., Johnston, A., Price, S. L., Nowell, H., Shankland, N. & Kennedy, A. R. (2006). J. Pharm. Sci. 95, Florence, A. J., Leech, C. K., Shankland, N., Shankland, K. & Johnston, A. (2006). CrystEngComm, 8, Harrison, W. T. A., Yathirajan, H. S. & Anilkumar, H. G. (2006). Acta Cryst. C62, o240 o242. Hooft, R. (1988). COLLECT. Nonius BV, Delft, The Netherlands. Leech, C. K., Florence, A. J., Shankland, K., Shankland, N. & Johnston, A. (2007a). Acta Cryst. E63, o675 o677. Leech, C. K., Florence, A. J., Shankland, K., Shankland, N. & Johnston, A. (2007b). Acta Cryst. E63, o205 o206. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp New York: Academic Press. Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Spek, A. L. (2003). J. Appl. Cryst. 36, o1470 Johnston et al. C 15 H 14 N 2 OCH 2 O 2
3 supporting information [ 10,11-Dihydrocarbamazepine formic acid solvate Andrea Johnston, Alastair J. Florence, Philippe Fernandes, Norman Shankland and Alan R. Kennedy 10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide methanoic acid (1/1) Crystal data C 15 H 14 N 2 O CH 2 O 2 M r = Triclinic, P1 a = (4) Å b = (12) Å c = (18) Å α = (5) β = (7) γ = (7) V = (14) Å 3 Data collection Nonius KappaCCD diffractometer Radiation source: fine-focus sealed tube Graphite monochromator φ and ω scans 9817 measured reflections 1956 independent reflections Refinement Refinement on F 2 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = wr(f 2 ) = S = reflections 202 parameters 0 restraints Primary atom site location: structure-invariant direct methods Z = 2 F(000) = 300 D x = Mg m 3 Mo Kα radiation, λ = Å Cell parameters from 1893 reflections θ = µ = 0.09 mm 1 T = 123 K Cut needle, colourless mm 1260 reflections with I > 2σ(I) R int = θ max = 23.0, θ min = 3.4 h = 5 5 k = l = Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H atoms treated by a mixture of independent and constrained refinement w = 1/[σ 2 (F o2 ) + (0.0384P) P] where P = (F o 2 + 2F c2 )/3 (Δ/σ) max < Δρ max = 0.21 e Å 3 Δρ min = 0.22 e Å 3 sup-1
4 Special details Experimental. Sample crystals twinned. "Single" small piece cut out from a larger, twinned sample. 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 F 2 against ALL reflections. The weighted R-factor wr and goodness of fit S are based on F 2, conventional R-factors R are based on F, with F set to zero for negative F 2. The threshold expression of F 2 > σ(f 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 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 (Å 2 ) x y z U iso */U eq O (3) (2) (13) (5) O (4) (2) (14) (6) O (4) (2) (15) (6) N (4) (2) (16) (6) N (5) (3) (19) (7) C (5) (3) (2) (7) C (5) (3) (2) (7) C (5) (3) (2) (8) H * C (5) (3) (2) (8) H * C (6) (3) (2) (8) H * C (5) (3) (2) (8) H * C (5) (3) (2) (7) C (5) (3) (2) (8) H8A * H8B * C (5) (3) (2) (8) H9A * H9B * C (5) (3) (2) (7) C (5) (3) (19) (7) C (5) (3) (2) (8) H * C (5) (3) (2) (8) H * C (6) (3) (2) (9) H * C (6) (3) (2) (8) H * C (5) (4) (2) (8) H * sup-2
5 H (7) (4) (3) (13)* H2A (6) (3) (2) (11)* H2B (5) (3) (19) (9)* Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 O (11) (13) (14) (9) (9) (10) O (13) (13) (14) (10) (10) (11) O (13) (14) (15) (10) (11) (12) N (12) (14) (15) (10) (11) (12) N (17) (18) (18) (13) (13) (15) C (16) (2) (2) (13) (14) (17) C (15) (17) (2) (13) (13) (15) C (17) (18) (2) (14) (14) (16) C (18) (19) (2) (15) (17) (17) C (19) (2) (2) (16) (16) (17) C (18) (19) (2) (15) (14) (16) C (16) (17) (2) (13) (14) (15) C (17) (19) (2) (14) (14) (16) C (16) (19) (2) (14) (14) (16) C (16) (19) (2) (14) (14) (16) C (16) (18) (18) (13) (13) (14) C (17) (2) (2) (14) (14) (16) C (19) (2) (2) (15) (15) (17) C (2) (18) (2) (17) (18) (18) C (19) (2) (2) (15) (16) (16) C (17) (2) (2) (16) (15) (18) Geometric parameters (Å, º) O1 C (3) C6 H O2 C (3) C7 C (4) O2 H (4) C8 C (4) O3 C (3) C8 H8A N1 C (3) C8 H8B N1 C (3) C9 C (4) N1 C (3) C9 H9A N2 C (4) C9 H9B N2 H2A 0.88 (3) C10 C (4) N2 H2B 0.89 (3) C10 C (4) C2 C (4) C11 C (4) C2 C (4) C12 C (4) C3 C (4) C12 H C3 H C13 C (4) C4 C (4) C13 H C4 H C14 C (4) C5 C (4) C14 H sup-3
6 C5 H C15 H C6 C (4) C16 H C16 O2 H2 112 (2) C7 C8 H8B C1 N1 C (2) C9 C8 H8B C1 N1 C (2) H8A C8 H8B C11 N1 C (2) C10 C9 C (2) C1 N2 H2A 114 (2) C10 C9 H9A C1 N2 H2B (18) C8 C9 H9A H2A N2 H2B 123 (3) C10 C9 H9B O1 C1 N (3) C8 C9 H9B O1 C1 N (3) H9A C9 H9B N2 C1 N (3) C15 C10 C (3) C7 C2 C (3) C15 C10 C (3) C7 C2 N (2) C11 C10 C (2) C3 C2 N (3) C12 C11 C (3) C4 C3 C (3) C12 C11 N (2) C4 C3 H C10 C11 N (2) C2 C3 H C13 C12 C (3) C3 C4 C (3) C13 C12 H C3 C4 H C11 C12 H C5 C4 H C12 C13 C (3) C4 C5 C (3) C12 C13 H C4 C5 H C14 C13 H C6 C5 H C13 C14 C (3) C5 C6 C (3) C13 C14 H C5 C6 H C15 C14 H C7 C6 H C10 C15 C (3) C2 C7 C (3) C10 C15 H C2 C7 C (3) C14 C15 H C6 C7 C (3) O3 C16 O (3) C7 C8 C (3) O3 C16 H C7 C8 H8A O2 C16 H C9 C8 H8A C11 N1 C1 O (2) C6 C7 C8 C (2) C2 N1 C1 O1 4.9 (4) C7 C8 C9 C (3) C11 N1 C1 N2 6.9 (4) C8 C9 C10 C (3) C2 N1 C1 N (2) C8 C9 C10 C (3) C1 N1 C2 C (3) C15 C10 C11 C (4) C11 N1 C2 C (3) C9 C10 C11 C (2) C1 N1 C2 C (3) C15 C10 C11 N (2) C11 N1 C2 C (3) C9 C10 C11 N1 2.6 (4) C7 C2 C3 C4 0.7 (4) C1 N1 C11 C (3) N1 C2 C3 C (2) C2 N1 C11 C (3) C2 C3 C4 C5 0.1 (4) C1 N1 C11 C (3) C3 C4 C5 C6 0.8 (4) C2 N1 C11 C (3) C4 C5 C6 C7 1.3 (4) C10 C11 C12 C (4) sup-4
7 C3 C2 C7 C6 0.3 (4) N1 C11 C12 C (2) N1 C2 C7 C (2) C11 C12 C13 C (4) C3 C2 C7 C (2) C12 C13 C14 C (4) N1 C2 C7 C8 2.2 (4) C11 C10 C15 C (4) C5 C6 C7 C2 0.7 (4) C9 C10 C15 C (3) C5 C6 C7 C (3) C13 C14 C15 C (4) C2 C7 C8 C9 3.1 (4) Hydrogen-bond geometry (Å, º) D H A D H H A D A D H A O2 H2 O (4) 1.52 (4) (3) 170 (4) N2 H2A O (3) 2.08 (3) (4) 163 (3) N2 H2B O3 i 0.89 (3) 2.13 (3) (4) 141 (2) Symmetry code: (i) x+1, y+1, z. sup-5
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