Cytenamide trifluoro­acetic acid solvate

Johnston, A.; Florence, A.J.; Fabbiani, F.J.A.; Shankland, K.; Bedford, C.T.; Bardin, J.

doi:10.1107/S1600536808016577

organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Pages o1215-o1216

doi:10.1107/S1600536808016577

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Cytenamide trifluoroacetic acid solvate

Andrea Johnston,^a Alastair J. Florence,^a ^* Francesca J. A. Fabbiani,^b Kenneth Shankland,^c Colin T. Bedford ^d and Julie Bardin ^a

^aSolid-State Research Group, Strathclyde Institute of Pharmacy and Biomedical Sciences, The John Arbuthnott Building, University of Strathclyde, 27 Taylor Street, Glasgow G4 0NR, Scotland, ^bUniversity of Göttingen, GZG, Department of Crystallography, Goldschmidtstrasse 1, D-37077 Göttingen, Germany, ^cISIS Facility, Rutherford Appleton Laboratory, Chilton, Didcot, Oxon OX11 0QX, England, and ^dUniversity College London, Department of Chemistry, 20 Gordon Street, London, WC1H 0AJ, England
^*Correspondence e-mail: alastair.florence@strath.ac.uk

(Received 19 May 2008; accepted 30 May 2008; online 7 June 2008)

Cytenamide forms a 1:1 solvate with trifluoroacetic acid (systematic name: 5H-dibenzo[a,d]cycloheptatriene-5-carboxamide trifluoroacetic acid solvate), C₁₆H₁₃NO·C₂HF₃O₂. The compound crystallizes with one molecule of cytenamide and one of trifluoroacetic acid in the asymmetric unit; these are linked by O—H⋯O and N—H⋯O hydrogen bonds to form an R₂²(8) motif. The trifluoromethyl group of the solvent molecule displays rotational disorder over two sites, with site-occupancy factors of 0.964 (4) and 0.036 (4).

Related literature

For details on the experimental methods used to obtain this form, see: Davis et al. (1964 ); Florence et al. (2003 ); Florence, Johnston, Fernandes et al. (2006 ). For literature on carbamazepine and other related structures, see: Cyr et al. (1987 ); Fleischman et al. (2003 ); Florence, Johnston, Price et al. (2006 ); Florence, Leech et al. (2006 ); Bandoli et al. (1992 ); Harrison et al. (2006 ); Leech et al. (2007 ); Florence, Bedford et al. (2008 ); Florence, Shankland et al. (2008 ); Fernandes et al. (2007 ). For hydrogen-bond motifs, see: Etter (1990 ); Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₆H₁₃NO·C₂HF₃O₂
M_r = 349.31
Monoclinic, P 2₁ /n
a = 12.1673 (11) Å
b = 6.3235 (6) Å
c = 21.4525 (15) Å
β = 101.932 (8)°
V = 1614.9 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 160 K
0.16 × 0.13 × 0.08 mm

Data collection

Oxford Diffraction Gemini S diffractometer
Absorption correction: multi-scan (ABSPACK/CrysAlis RED; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD, CrysAlis RED and ABSPACK. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.83, T_max = 0.99
10796 measured reflections
2995 independent reflections
1423 reflections with I > 2σ(I)
R_int = 0.094

Refinement

R[F² > 2σ(F²)] = 0.080
wR(F²) = 0.178
S = 1.04
2984 reflections
236 parameters
24 restraints
H-atom parameters not refined
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.60 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H5⋯O2ⁱ	0.89	1.58	2.462 (4)	173
N1—H11⋯O1ⁱⁱ	0.86	2.23	2.976 (4)	144
N1—H12⋯O1ⁱⁱⁱ	0.87	2.16	2.982 (5)	159
Symmetry codes: (i) x, y-1, z; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x, y+1, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD, CrysAlis RED and ABSPACK. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD, CrysAlis RED and ABSPACK. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: publCIF (Westrip, 2008 ) and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S1600536808016577/cf2202sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808016577/cf2202Isup2.hkl

checkCIF report

Comment top

Cytenamide (CYT) is an analogue of carbamazepine (CBZ), a dibenzazepine drug used to control seizures (Cyr et al., 1987). Cytenamide-trifluoroacetic acid solvate (CYT-TFAA) was produced during an automated parallel crystallization study (Florence, Johnston, Fernandes et al., 2006) of CYT as part of a wider investigation that couples automated parallel crystallization with crystal structure prediction methodology to investigate the basic science underlying the solid-state diversity of CBZ (Florence, Johnston, Price et al., 2006; Florence, Leech et al., 2006) and its closely related analogues: CYT (Florence, Bedford et al., 2008), 10,11-dihydrocarbamazepine (Bandoli et al., 1992; Harrison et al., 2006; Leech et al., 2007) and cyheptamide (Florence, Shankland et al., 2008). 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 TFAA solution by slow evaporation at 278 K yielded a sample suitable for single-crystal X-ray diffraction (Fig. 1).

The compound crystallizes in space group P2₁/n with one molecule of CBZ and one molecule of TFAA in the asymmetric unit. As in the structure of CBZ-TFAA solvate (Fernandes et al., 2007) the solvent molecule displays rotational disorder and the fluorine atoms were refined over two sites yielding site occupancy factors 0.964 (4), 0.036 (4) and 0.53 (1), 0.47 (1) for CYT-TFAA and CBZ-TFAA respectively. The molecules also adopt a hydrogen-bonded arrangement similar to that observed in CBZ-TFAA solvate whereby the amide group of each CYT molecule is connected to the carboxylic acid group of a TFAA molecule by N–H···O and O–H···O contacts (Table 1) to form an R₂²(8) hydrogen-bonded motif (Etter, 1990; Bernstein et al., 1995). CYT also forms a second N—H···O contact with an adjacent solvent molecule to form a chain extending along the [010] direction.

Related literature top

For details on the experimental methods used to obtain this form, see: Davis et al. (1964); Florence et al. (2003); Florence, Johnston, Fernandes et al. (2006). For literature on carbamazepine and other related structures, see: Cyr et al. (1987); Fleischman et al. (2003); Florence, Johnston, Price et al. (2006); Florence, Leech et al. (2006); Bandoli et al. (1992); Harrison et al. (2006); Leech et al. (2007); Florence, Bedford et al. (2008); Florence, Shankland et al. (2008); Fernandes et al. (2007). For hydrogen-bond motifs, see: Etter (1990); Bernstein et al. (1995).

Experimental top

A sample of cytenamide was synthesized according to a modification of the published method (Davis et al., 1964). A single-crystal sample of cytenamide-TFAA was grown from a saturated TFAA solution by isothermal solvent evaporation at 278 K.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of CYT-TFAA, showing 50% probablility displacement ellipsoids. The lower occupancy fluorine atoms have beem omitted for clarity.
	Fig. 2. Hydrogen-bonded contacts in CYT-TFAA, showing the adjacent R₂²(8) CYT-TFAA units further linked by an N—H···O interaction. Minor ocupancy components have been omitted for clarity. CYT and TFAA molecules are coloured according to symmetry equivalence (green and blue respectively) and hydrogen bonds are shown as dashed lines.

5H-dibenzo[a,d]cycloheptatriene-5-carboxamide trifluoroacetic acid solvate top

Crystal data top

C₁₆H₁₃NO·C₂HF₃O₂	F(000) = 720
M_r = 349.31	D_x = 1.437 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1137 reflections
a = 12.1673 (11) Å	θ = 3–25°
b = 6.3235 (6) Å	µ = 0.12 mm⁻¹
c = 21.4525 (15) Å	T = 160 K
β = 101.932 (8)°	Block, colourless
V = 1614.9 (2) Å³	0.16 × 0.13 × 0.08 mm
Z = 4

Data collection top

Oxford Diffraction Gemini S diffractometer	2995 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1423 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.094
Detector resolution: 15.9745 pixels mm^-1	θ_max = 25.5°, θ_min = 3.1°
ϕ and ω scans	h = −14→14
Absorption correction: multi-scan (ABSPACK/CrysAlis RED; Oxford Diffraction, 2006)	k = 0→7
T_min = 0.83, T_max = 0.99	l = 0→25
10796 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.080	H-atom parameters not refined
wR(F²) = 0.178	Method = Modified Sheldrick w = 1/[σ²(F²) + ( 0.06P)² + 0.42P] , where P = (max(F_o²,0) + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.000413
2984 reflections	Δρ_max = 0.73 e Å⁻³
236 parameters	Δρ_min = −0.60 e Å⁻³
24 restraints

Crystal data top

C₁₆H₁₃NO·C₂HF₃O₂	V = 1614.9 (2) Å³
M_r = 349.31	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.1673 (11) Å	µ = 0.12 mm⁻¹
b = 6.3235 (6) Å	T = 160 K
c = 21.4525 (15) Å	0.16 × 0.13 × 0.08 mm
β = 101.932 (8)°

Data collection top

Oxford Diffraction Gemini S diffractometer	2995 independent reflections
Absorption correction: multi-scan (ABSPACK/CrysAlis RED; Oxford Diffraction, 2006)	1423 reflections with I > 2σ(I)
T_min = 0.83, T_max = 0.99	R_int = 0.094
10796 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.080	24 restraints
wR(F²) = 0.178	H-atom parameters not refined
S = 1.05	Δρ_max = 0.73 e Å⁻³
2984 reflections	Δρ_min = −0.60 e Å⁻³
236 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.6284 (3)	0.6720 (7)	0.3296 (2)	0.0461
C2	0.5488 (4)	0.4854 (7)	0.31163 (18)	0.0431
C3	0.4806 (3)	0.4971 (7)	0.24379 (18)	0.0380
C4	0.4965 (4)	0.3481 (7)	0.1996 (2)	0.0507
C5	0.4406 (4)	0.3618 (8)	0.1366 (2)	0.0578
C6	0.3726 (4)	0.5332 (9)	0.1180 (2)	0.0576
C7	0.3553 (4)	0.6826 (8)	0.16104 (19)	0.0519
C8	0.4077 (3)	0.6646 (7)	0.22567 (17)	0.0393
C9	0.3794 (4)	0.8214 (7)	0.2691 (2)	0.0475
C10	0.3773 (3)	0.7968 (7)	0.33147 (19)	0.0456
C11	0.4028 (3)	0.6095 (7)	0.37105 (18)	0.0369
C12	0.3488 (4)	0.5854 (7)	0.42250 (19)	0.0470
C13	0.3646 (4)	0.4094 (8)	0.45999 (18)	0.0515
C14	0.4337 (4)	0.2524 (8)	0.4474 (2)	0.0570
C15	0.4912 (4)	0.2755 (7)	0.3988 (2)	0.0497
C16	0.4774 (3)	0.4536 (7)	0.36104 (17)	0.0374
C17	0.8909 (4)	0.3112 (8)	0.4387 (2)	0.0572
C18	0.8197 (3)	0.1386 (7)	0.4008 (2)	0.0461
N1	0.6679 (3)	0.7697 (6)	0.28446 (15)	0.0533
O1	0.7936 (2)	0.1490 (5)	0.34338 (13)	0.0564
O2	0.6593 (2)	0.7215 (5)	0.38684 (12)	0.0591
O3	0.7904 (3)	−0.0019 (5)	0.43735 (12)	0.0618
F1	0.9217 (4)	0.4524 (6)	0.40116 (15)	0.1040	0.964 (4)
F2	0.9828 (2)	0.2331 (5)	0.47540 (13)	0.0714	0.964 (4)
F3	0.8361 (3)	0.4082 (5)	0.47792 (16)	0.0845	0.964 (4)
F4	0.846 (3)	0.502 (2)	0.429 (3)	0.0800*	0.036 (4)
F5	0.992 (2)	0.330 (8)	0.425 (3)	0.0800*	0.036 (4)
F6	0.910 (5)	0.282 (6)	0.5010 (4)	0.0800*	0.036 (4)
H11	0.6461	0.7332	0.2450	0.0619*
H12	0.7150	0.8730	0.2945	0.0619*
H21	0.5969	0.3601	0.3139	0.0495*
H41	0.5449	0.2331	0.2125	0.0596*
H51	0.4499	0.2559	0.1077	0.0680*
H61	0.3386	0.5487	0.0754	0.0651*
H71	0.3068	0.7953	0.1473	0.0581*
H91	0.3579	0.9563	0.2521	0.0539*
H101	0.3556	0.9169	0.3516	0.0541*
H121	0.3022	0.6959	0.4312	0.0539*
H131	0.3278	0.3947	0.4943	0.0619*
H141	0.4423	0.1260	0.4713	0.0647*
H151	0.5414	0.1676	0.3914	0.0557*
H5	0.7404	−0.0935	0.4169	0.0888*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.033 (2)	0.065 (3)	0.040 (3)	−0.002 (2)	0.005 (2)	0.003 (2)
C2	0.036 (2)	0.047 (3)	0.044 (2)	0.008 (2)	0.002 (2)	−0.006 (2)
C3	0.028 (2)	0.046 (3)	0.041 (2)	−0.007 (2)	0.0095 (19)	−0.007 (2)
C4	0.044 (3)	0.056 (3)	0.052 (3)	0.000 (2)	0.011 (2)	−0.009 (2)
C5	0.056 (3)	0.072 (4)	0.048 (3)	−0.012 (3)	0.015 (2)	−0.021 (3)
C6	0.053 (3)	0.081 (4)	0.036 (3)	−0.011 (3)	0.002 (2)	−0.003 (3)
C7	0.044 (3)	0.070 (3)	0.041 (3)	−0.004 (2)	0.004 (2)	0.002 (3)
C8	0.030 (2)	0.049 (3)	0.038 (2)	−0.003 (2)	0.0052 (19)	0.000 (2)
C9	0.047 (3)	0.041 (3)	0.055 (3)	0.002 (2)	0.009 (2)	−0.001 (2)
C10	0.047 (3)	0.045 (3)	0.047 (3)	0.003 (2)	0.013 (2)	−0.006 (2)
C11	0.036 (2)	0.037 (3)	0.035 (2)	−0.006 (2)	0.0022 (19)	−0.006 (2)
C12	0.047 (3)	0.056 (3)	0.038 (2)	−0.005 (2)	0.008 (2)	−0.011 (2)
C13	0.050 (3)	0.069 (4)	0.035 (2)	−0.014 (3)	0.007 (2)	0.006 (3)
C14	0.058 (3)	0.057 (3)	0.050 (3)	−0.010 (3)	−0.004 (2)	0.011 (3)
C15	0.043 (3)	0.055 (3)	0.048 (3)	−0.003 (2)	0.001 (2)	0.002 (2)
C16	0.040 (3)	0.036 (3)	0.032 (2)	−0.002 (2)	−0.0011 (19)	−0.003 (2)
C17	0.054 (3)	0.064 (4)	0.055 (3)	−0.003 (3)	0.014 (3)	−0.002 (3)
C18	0.034 (3)	0.060 (3)	0.044 (3)	0.002 (2)	0.007 (2)	0.008 (3)
N1	0.043 (2)	0.078 (3)	0.038 (2)	−0.017 (2)	0.0045 (17)	−0.009 (2)
O1	0.0488 (19)	0.082 (2)	0.0375 (17)	−0.0082 (17)	0.0064 (14)	0.0091 (17)
O2	0.054 (2)	0.090 (3)	0.0300 (17)	−0.0283 (18)	0.0024 (14)	−0.0002 (16)
O3	0.060 (2)	0.085 (2)	0.0362 (17)	−0.0297 (19)	−0.0009 (15)	0.0067 (17)
F1	0.132 (3)	0.101 (3)	0.074 (2)	−0.059 (3)	0.008 (2)	0.020 (2)
F2	0.0448 (18)	0.091 (2)	0.0715 (19)	−0.0066 (16)	−0.0045 (14)	−0.0160 (17)
F3	0.075 (2)	0.086 (2)	0.095 (2)	0.0090 (19)	0.0230 (19)	−0.027 (2)

Geometric parameters (Å, º) top

C1—C2	1.525 (6)	C11—C16	1.386 (5)
C1—N1	1.321 (5)	C12—C13	1.363 (6)
C1—O2	1.247 (4)	C12—H121	0.942
C2—C3	1.521 (5)	C13—C14	1.364 (6)
C2—C16	1.517 (6)	C13—H131	0.942
C2—H21	0.980	C14—C15	1.378 (6)
C3—C4	1.379 (6)	C14—H141	0.945
C3—C8	1.384 (5)	C15—C16	1.376 (5)
C4—C5	1.383 (6)	C15—H151	0.951
C4—H41	0.941	C17—C18	1.520 (5)
C5—C6	1.372 (7)	C17—F1	1.307 (4)
C5—H51	0.936	C17—F2	1.322 (5)
C6—C7	1.368 (6)	C17—F3	1.328 (5)
C6—H61	0.928	C17—C18	1.520 (5)
C7—C8	1.406 (5)	C17—F4	1.323 (7)
C7—H71	0.934	C17—F5	1.323 (7)
C8—C9	1.451 (5)	C17—F6	1.323 (7)
C9—C10	1.352 (5)	C18—O1	1.209 (4)
C9—H91	0.944	C18—O3	1.283 (5)
C10—C11	1.453 (6)	N1—H11	0.865
C10—H101	0.938	N1—H12	0.867
C11—C12	1.405 (5)	O3—H5	0.887

C2—C1—N1	119.0 (4)	C12—C11—C16	118.2 (4)
C2—C1—O2	119.3 (4)	C11—C12—C13	121.4 (4)
N1—C1—O2	121.6 (4)	C11—C12—H121	118.3
C1—C2—C3	113.4 (4)	C13—C12—H121	120.4
C1—C2—C16	110.5 (3)	C12—C13—C14	119.6 (4)
C3—C2—C16	113.4 (3)	C12—C13—H131	120.7
C1—C2—H21	105.8	C14—C13—H131	119.7
C3—C2—H21	106.9	C13—C14—C15	120.2 (4)
C16—C2—H21	106.2	C13—C14—H141	120.7
C2—C3—C4	119.9 (4)	C15—C14—H141	119.0
C2—C3—C8	119.8 (4)	C14—C15—C16	120.8 (4)
C4—C3—C8	120.2 (4)	C14—C15—H151	119.6
C3—C4—C5	121.2 (4)	C16—C15—H151	119.6
C3—C4—H41	119.6	C2—C16—C11	120.1 (4)
C5—C4—H41	119.2	C2—C16—C15	120.1 (4)
C4—C5—C6	118.6 (4)	C11—C16—C15	119.7 (4)
C4—C5—H51	120.0	C18—C17—F1	111.5 (4)
C6—C5—H51	121.3	C18—C17—F2	111.6 (4)
C5—C6—C7	121.1 (4)	F1—C17—F2	107.9 (4)
C5—C6—H61	119.4	C18—C17—F3	111.4 (4)
C7—C6—H61	119.5	F1—C17—F3	108.7 (4)
C6—C7—C8	120.6 (4)	F2—C17—F3	105.6 (4)
C6—C7—H71	119.3	C18—C17—F4	113.56 (6)
C8—C7—H71	120.1	C18—C17—F5	113.57 (6)
C7—C8—C3	118.2 (4)	F4—C17—F5	105.08 (7)
C7—C8—C9	117.4 (4)	C18—C17—F6	113.57 (6)
C3—C8—C9	124.4 (4)	F4—C17—F6	105.08 (7)
C8—C9—C10	127.8 (4)	F5—C17—F6	105.08 (7)
C8—C9—H91	116.8	C17—C18—O1	120.4 (4)
C10—C9—H91	115.3	C17—C18—O3	111.8 (4)
C9—C10—C11	128.8 (4)	O1—C18—O3	127.8 (4)
C9—C10—H101	115.3	C1—N1—H11	120.6
C11—C10—H101	115.9	C1—N1—H12	119.5
C10—C11—C12	118.0 (4)	H11—N1—H12	119.9
C10—C11—C16	123.9 (4)	C18—O3—H5	113.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H5···O2ⁱ	0.89	1.58	2.462 (4)	173
N1—H11···O1ⁱⁱ	0.86	2.23	2.976 (4)	144
N1—H12···O1ⁱⁱⁱ	0.87	2.16	2.982 (5)	159

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃NO·C₂HF₃O₂
M_r	349.31
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	160
a, b, c (Å)	12.1673 (11), 6.3235 (6), 21.4525 (15)
β (°)	101.932 (8)
V (Å³)	1614.9 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.16 × 0.13 × 0.08

Data collection
Diffractometer	Oxford Diffraction Gemini S diffractometer
Absorption correction	Multi-scan (ABSPACK/CrysAlis RED; Oxford Diffraction, 2006)
T_min, T_max	0.83, 0.99
No. of measured, independent and observed [I > 2σ(I)] reflections	10796, 2995, 1423
R_int	0.094
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.080, 0.178, 1.05
No. of reflections	2984
No. of parameters	236
No. of restraints	24
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.60

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), CRYSTALS (Betteridge et al., 2003), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006), publCIF (Westrip, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H5···O2ⁱ	0.89	1.58	2.462 (4)	173
N1—H11···O1ⁱⁱ	0.86	2.23	2.976 (4)	144
N1—H12···O1ⁱⁱⁱ	0.87	2.16	2.982 (5)	159

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

Acknowledgements

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 (www.cposs.org.uk).

References

Bandoli, G., Nicolini, M., Ongaro, A., Volpe, G. & Rubello, A. (1992). J. Chem. Crystallogr. 22, 177–183. CAS Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487. Web of Science CrossRef IUCr Journals Google Scholar
Blessing, R. H. (1997). J. Appl. Cryst. 30, 421–426. CrossRef CAS Web of Science IUCr Journals Google Scholar
Cyr, T. D., Matsui, F., Sears, R. W., Curran, N. M. & Lovering, E. G. (1987). J. Assoc. Off. Anal. Chem. 30, 421–426. Google Scholar
Davis, M. A., Winthrop, S. O., Thomas, R. A., Herr, F., Charest, M.-P. & Gaudry, R. (1964). J. Med. Chem. 7, 88–94. CrossRef PubMed CAS Web of Science Google Scholar
Etter, M. C. (1990). Acc. Chem. Res. 23, 120–126. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Fernandes, P., Bardin, J., Johnston, A., Florence, A. J., Leech, C. K., David, W. I. F. & Shankland, K. (2007). Acta Cryst. E63, o4269. Web of Science CSD CrossRef IUCr Journals Google Scholar
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, 909–919. Web of Science CSD CrossRef CAS Google Scholar
Florence, A. J., Baumgartner, B., Weston, C., Shankland, N., Kennedy, A. R., Shankland, K. & David, W. I. F. (2003). J. Pharm. Sci. 92, 1930–1938. Web of Science CSD CrossRef PubMed CAS Google Scholar
Florence, A. J., Bedford, C. T., Fabbiani, F. P. A., Shankland, K., Gelbrich, T., Hursthouse, M. B., Shankland, N., Johnston, A. & Fernandes, P. (2008). CrystEngComm, DOI: 10.1039/b719717a. Google Scholar
Florence, A. J., Johnston, A., Fernandes, P., Shankland, N. & Shankland, K. (2006). J. Appl. Cryst. 39, 922–924. Web of Science CrossRef CAS IUCr Journals Google Scholar
Florence, A. J., Johnston, A., Price, S. L., Nowell, H., Kennedy, A. R. & Shankland, N. (2006). J. Pharm. Sci. 95, 1918–1930. Web of Science CrossRef PubMed CAS Google Scholar
Florence, A. J., Leech, C. K., Shankland, N., Shankland, K. & Johnston, A. (2006). CrystEngComm, 8, 746–747. Web of Science CSD CrossRef CAS Google Scholar
Florence, A. J., Shankland, K., Gelbrich, T., Hursthouse, M. B., Shankland, N., Johnston, A., Fernandes, P. & Leech, C. K. (2008). CrystEngComm, 10, 26–28. Web of Science CSD CrossRef CAS Google Scholar
Harrison, W. T. A., Yathirajan, H. S. & Anilkumar, H. G. (2006). Acta Cryst. C62, o240–o242. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Leech, C. K., Florence, A. J., Shankland, K., Shankland, N. & Johnston, A. (2007). Acta Cryst. E63, o675–o677. CSD CrossRef IUCr Journals Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Oxford Diffraction (2006). CrysAlis CCD, CrysAlis RED and ABSPACK. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar