organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

N-(2,6-Di­methyl­phen­yl)-2-(2-thien­yl)acetamide

aFioCruz – Fundação Oswaldo Cruz, Instituto de Tecnologia em Farmacos–FarManguinhos, Rua Sizenando Nabuco, 100, Manguinhos, 21041-250 Rio de Janeiro, RJ, Brazil, bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, cCentro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos, Av. Brasil 4365, 21040-900 Rio de Janeiro, RJ, Brazil, and dCHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland
*Correspondence e-mail: edward.tiekink@gmail.com

(Received 19 November 2009; accepted 20 November 2009; online 25 November 2009)

The thienyl ring in the title compound, C14H15NOS, is disordered over two diagonally opposite positions, the major component having a site-occupancy factor of 0.569 (3). The mol­ecule is highly twisted with respect to the central amide group, which is reflected in the dihedral angle formed between the thienyl and benzene rings of 77.01 (15)° [70.34 (18)° for the minor component]. In the crystal, mol­ecules self-associate into chains along [100] via N—H⋯O hydrogen bonds. The chains are reinforced by complementary C—H⋯O contacts.

Related literature

For a general overview of 2-substituted thio­phenes, see: Campaigne (1984[Campaigne, E. (1984). In Comprehensive Heterocyclic Chemistry, Vol. 4, edited by A. R. Katritzky C. W. & Rees, pp. 863-934. Oxford: Pergamon.]); Kleemann et al. (2006[Kleemann, A., Engel, J. B., Kutscher, B. & Reichert, D. (2006). Pharmaceutical Substances. New York, Stuttgart: Georg Thieme Verlag.]). For recent bio­logical studies on 2-substituted thio­phenes, see: Lourenço et al. (2007[Lourenço, M. C. S., Vicente, F. R., Henriques, M., das, G. M. de O., Candéa, A. L. P., Gonçalves, R. S. B., Nogueira, T. C. M., Ferreira, M. de L. & de Souza, M. V. N. (2007). Bioorg. Med. Chem. Lett. 17, 6895-6898.]).

[Scheme 1]

Experimental

Crystal data
  • C14H15NOS

  • Mr = 245.34

  • Triclinic, [P \overline 1]

  • a = 4.7489 (2) Å

  • b = 11.7309 (5) Å

  • c = 11.8117 (4) Å

  • α = 100.981 (2)°

  • β = 95.427 (2)°

  • γ = 101.104 (2)°

  • V = 627.96 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.24 mm−1

  • T = 120 K

  • 0.16 × 0.06 × 0.02 mm

Data collection
  • Nonius KappaCCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.896, Tmax = 1.000

  • 11243 measured reflections

  • 2840 independent reflections

  • 2388 reflections with I > 2σ(I)

  • Rint = 0.043

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.121

  • S = 1.04

  • 2840 reflections

  • 175 parameters

  • H-atom parameters constrained

  • Δρmax = 0.27 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O1i 0.88 2.04 2.8701 (18) 157
C5—H5b⋯O1i 0.99 2.38 3.2622 (19) 148
Symmetry code: (i) x-1, y, z.

Data collection: COLLECT (Hooft, 1998[Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Comment top

2-Substituted thiophenes have been found to have various uses, for example as dyestuffs, flavour agents, drugs, and inhibitors (Campaigne, 1984). Indeed, thiophenes are present in many natural and synthetic products with a wide range of pharmacological activities (Kleemann et al., 2006). The in vitro anti-mycobacterial activities of a series of N-(aryl)-2-thiophen-2-ylacetamide derivatives were recently investigated (Lourenço et al., 2007): encouraging activities were detected for some derivatives. The search for new drugs having anti-bacterial activity against Mycobacterium tuberculosis is a vital task due to the increase of multi-drug resistant tuberculosis (MDR-TB) and AIDS cases worldwide and the increasing resistance to the currently used main line drugs such as isoniazid and rifampin (http://www.who.int/tdr/diseases/tb/default.htm). It was in this context that the title compound, (I), was synthesized.

The central O1, N1, C5 and C6 moiety in (I), Fig. 1, is planar with the maximum deviation from the least-squares plane through these atoms being 0.0072 (13) Å for the C6 atom. Otherwise, the molecule is highly twisted as seen in the values of the S1–C1–C5–C6 and C6–N1–C7–C8 torsion angles of 102.98 (15) ° (-69.07 (18) ° for the minor component of the thienyl ring) and -116.27 (17) °, respectively. The dihedral angle between the planes through the thienyl and benzene rings are 77.01 (15) and 70.34 (18) ° for the major and minor components of the disordered thienyl ring, respectively.

In the crystal structure, molecules are connected into linear supramolecular chains via C(4), {···HNC(O)}, synthons, Table 1 and Fig. 2. Chains, which are aligned along [1 0 0], are reinforced by complementary C5–H···O1 contacts, Table 1, so that the acceptor carbonyl-O1 atom is bifurcated.

Related literature top

For a general overview of 2-substituted thiophenes, see: Campaigne (1984); Kleemann et al. (2006). For recent biological studies on 2-substituted thiophenes, see: Lourenço et al. (2007).

Experimental top

A solution of 2,6-dimethylaniline (2 mmol) and 2-thienylacetyl chloride (2 mmol) in tetrahydrofuran (20 ml), was stirred for 2 h at room temperature, water (30 ml) added and the mixture was extracted with ethyl acetate (2 x 20 ml). The combined organic layers were washed with saturated aqueous NaHCO3 and brine, dried over MgSO4, filtered, and rotary evaporated to give the crude product, (yield 90%) which was recrystallized twice from EtOH. m. pt.: 405–406 K; CG/MS: m/z [M]+.: 245. 1H NMR [500.00 MHz, DMSO-d6] δ: 9.46 (s, 1H, NH), 7.38 (dd, 1H, J = 6.5, 2.0 Hz), 7.05–6.97 (m, 5H), 3.82 (s, 2H, CH2CO), 2.09 (s, 6H, Me) p.p.m. 13C NMR (125.0 MHz, DMSO-d6) δ: 167.7, 137.6, 135.1, 134.8, 127.6, 126.6, 126.4, 126.2, 124.8, 36.5, 17.9 p.p.m. IR (KBr, cm-1): νmax 1644 (CO).

Refinement top

All H atoms were geometrically placed (N–H = 0.88 Å and C–H = 0.95–0.99 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(N, C). The thienyl ring was disordered with two diagonally opposed positions resolved for the S1 and C4 atoms. The major component had a site occupancy factor = 0.569 (3).

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Molecular structure (I) showing atom-labelling scheme and displacement ellipsoids at the 50% probability level. Only the major component of the disordered thienyl ring is shown for reasons of clarity.
[Figure 2] Fig. 2. Supramolecular chain in (I) mediated by N–H···O hydrogen bonds (blue dashed lines). Colour code: S, yellow; O, red; N, blue; C, grey; and H, green.
N-(2,6-Dimethylphenyl)-2-(2-thienyl)acetamide top
Crystal data top
C14H15NOSZ = 2
Mr = 245.34F(000) = 260
Triclinic, P1Dx = 1.298 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 4.7489 (2) ÅCell parameters from 2752 reflections
b = 11.7309 (5) Åθ = 2.9–27.5°
c = 11.8117 (4) ŵ = 0.24 mm1
α = 100.981 (2)°T = 120 K
β = 95.427 (2)°Block, pale-brown
γ = 101.104 (2)°0.16 × 0.06 × 0.02 mm
V = 627.96 (4) Å3
Data collection top
Nonius KappaCCD area-detector
diffractometer
2840 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode2388 reflections with I > 2σ(I)
10 cm confocal mirrors monochromatorRint = 0.043
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.6°
ϕ and ω scansh = 66
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 1515
Tmin = 0.896, Tmax = 1.000l = 1415
11243 measured reflections
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0468P)2 + 0.4276P]
where P = (Fo2 + 2Fc2)/3
2840 reflections(Δ/σ)max < 0.001
175 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C14H15NOSγ = 101.104 (2)°
Mr = 245.34V = 627.96 (4) Å3
Triclinic, P1Z = 2
a = 4.7489 (2) ÅMo Kα radiation
b = 11.7309 (5) ŵ = 0.24 mm1
c = 11.8117 (4) ÅT = 120 K
α = 100.981 (2)°0.16 × 0.06 × 0.02 mm
β = 95.427 (2)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
2840 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
2388 reflections with I > 2σ(I)
Tmin = 0.896, Tmax = 1.000Rint = 0.043
11243 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.121H-atom parameters constrained
S = 1.04Δρmax = 0.27 e Å3
2840 reflectionsΔρmin = 0.21 e Å3
175 parameters
Special details top

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 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 (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.5541 (2)0.54877 (11)0.35576 (11)0.0269 (3)
N10.1431 (3)0.61274 (11)0.31337 (12)0.0198 (3)
H10.04730.59490.30560.024*
C10.0819 (3)0.31943 (14)0.26257 (15)0.0227 (3)0.569 (3)
S10.2856 (3)0.21398 (11)0.27132 (12)0.0304 (3)0.569 (3)
C20.1372 (5)0.14166 (18)0.13388 (18)0.0401 (5)0.569 (3)
H20.18100.06800.10000.048*0.569 (3)
C30.0428 (5)0.19078 (19)0.0743 (2)0.0431 (5)0.569 (3)
H30.12830.16530.00480.052*0.569 (3)
C40.0767 (15)0.2938 (6)0.1609 (6)0.0469 (15)0.569 (3)
H40.21080.34050.14320.056*0.569 (3)
C1'0.0819 (3)0.31943 (14)0.26257 (15)0.0227 (3)0.431 (3)
S1'0.1147 (5)0.32153 (18)0.13045 (17)0.0394 (5)0.431 (3)
C2'0.0428 (5)0.19078 (19)0.0743 (2)0.0431 (5)0.431 (3)
H2'0.13180.15000.00180.052*0.431 (3)
C3'0.1372 (5)0.14166 (18)0.13388 (18)0.0401 (5)0.431 (3)
H3'0.21570.07410.10850.048*0.431 (3)
C4'0.1802 (19)0.2208 (7)0.2491 (7)0.0390 (18)0.431 (3)
H4'0.27870.20090.31400.047*0.431 (3)
C50.1040 (3)0.42001 (14)0.36525 (14)0.0216 (3)
H5A0.19110.39950.43620.026*
H5B0.09220.43260.37740.026*
C60.2889 (3)0.53354 (14)0.34521 (13)0.0199 (3)
C70.2832 (3)0.72479 (14)0.29151 (14)0.0203 (3)
C80.2477 (3)0.82854 (14)0.36467 (14)0.0220 (3)
C90.3851 (4)0.93774 (15)0.34462 (16)0.0279 (4)
H90.36091.00930.39220.033*
C100.5560 (4)0.94333 (16)0.25656 (17)0.0313 (4)
H100.65301.01830.24530.038*
C110.5854 (4)0.83976 (17)0.18487 (16)0.0308 (4)
H110.70230.84460.12430.037*
C120.4471 (4)0.72805 (16)0.19947 (14)0.0254 (4)
C130.0684 (4)0.82262 (15)0.46287 (15)0.0261 (4)
H13A0.13230.78300.43110.039*
H13B0.07400.90340.50590.039*
H13C0.14690.77760.51550.039*
C140.4706 (4)0.61673 (17)0.11603 (16)0.0339 (4)
H14A0.55330.63810.04810.051*
H14B0.27760.56520.09090.051*
H14C0.59620.57450.15490.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0159 (5)0.0303 (6)0.0356 (7)0.0055 (5)0.0035 (5)0.0094 (5)
N10.0142 (6)0.0179 (6)0.0263 (7)0.0014 (5)0.0030 (5)0.0043 (5)
C10.0207 (7)0.0205 (8)0.0270 (8)0.0030 (6)0.0047 (6)0.0062 (6)
S10.0376 (7)0.0255 (5)0.0302 (6)0.0155 (5)0.0043 (5)0.0023 (4)
C20.0515 (12)0.0277 (10)0.0373 (11)0.0033 (9)0.0092 (9)0.0013 (8)
C30.0420 (11)0.0397 (11)0.0403 (11)0.0010 (9)0.0047 (9)0.0009 (9)
C40.056 (3)0.041 (3)0.044 (4)0.019 (2)0.007 (2)0.009 (2)
C1'0.0207 (7)0.0205 (8)0.0270 (8)0.0030 (6)0.0047 (6)0.0062 (6)
S1'0.0444 (8)0.0388 (10)0.0304 (10)0.0132 (7)0.0092 (7)0.0009 (6)
C2'0.0420 (11)0.0397 (11)0.0403 (11)0.0010 (9)0.0047 (9)0.0009 (9)
C3'0.0515 (12)0.0277 (10)0.0373 (11)0.0033 (9)0.0092 (9)0.0013 (8)
C4'0.040 (4)0.044 (4)0.036 (4)0.011 (3)0.002 (3)0.014 (3)
C50.0204 (7)0.0190 (7)0.0258 (8)0.0043 (6)0.0043 (6)0.0051 (6)
C60.0184 (7)0.0213 (7)0.0188 (7)0.0042 (6)0.0030 (6)0.0015 (6)
C70.0165 (7)0.0204 (8)0.0229 (8)0.0016 (6)0.0004 (6)0.0059 (6)
C80.0182 (7)0.0226 (8)0.0248 (8)0.0033 (6)0.0017 (6)0.0059 (6)
C90.0275 (8)0.0218 (8)0.0345 (9)0.0047 (7)0.0040 (7)0.0073 (7)
C100.0306 (9)0.0266 (9)0.0372 (10)0.0013 (7)0.0058 (8)0.0146 (8)
C110.0309 (9)0.0358 (10)0.0270 (9)0.0022 (7)0.0095 (7)0.0125 (8)
C120.0238 (8)0.0298 (9)0.0224 (8)0.0053 (7)0.0028 (6)0.0060 (7)
C130.0241 (8)0.0217 (8)0.0321 (9)0.0038 (6)0.0088 (7)0.0033 (7)
C140.0389 (10)0.0379 (10)0.0237 (9)0.0065 (8)0.0103 (8)0.0024 (8)
Geometric parameters (Å, º) top
O1—C61.2285 (19)C4'—H4'0.9500
N1—C61.347 (2)C5—C61.520 (2)
N1—C71.4360 (19)C5—H5A0.9900
N1—H10.8800C5—H5B0.9900
C1—C41.305 (7)C7—C121.398 (2)
C1—C51.502 (2)C7—C81.401 (2)
C1—S11.723 (2)C8—C91.395 (2)
S1—C21.697 (2)C8—C131.507 (2)
C2—C31.337 (3)C9—C101.382 (3)
C2—H20.9500C9—H90.9500
C3—C41.472 (7)C10—C111.382 (3)
C3—H30.9500C10—H100.9500
C4—H40.9500C11—C121.398 (2)
C1'—C4'1.317 (9)C11—H110.9500
C1'—C51.502 (2)C12—C141.509 (2)
C1'—S1'1.748 (3)C13—H13A0.9800
S1'—C2'1.663 (3)C13—H13B0.9800
C2'—C3'1.337 (3)C13—H13C0.9800
C2'—H2'0.9500C14—H14A0.9800
C3'—C4'1.466 (8)C14—H14B0.9800
C3'—H3'0.9500C14—H14C0.9800
C6—N1—C7123.24 (13)C6—C5—H5B109.6
C6—N1—H1118.4H5A—C5—H5B108.1
C7—N1—H1118.4O1—C6—N1123.38 (15)
C4—C1—C5130.6 (3)O1—C6—C5120.78 (14)
C4—C1—S1109.9 (3)N1—C6—C5115.82 (13)
C5—C1—S1119.57 (13)C12—C7—C8122.10 (14)
C2—S1—C189.60 (12)C12—C7—N1120.16 (14)
C3—C2—S1118.43 (17)C8—C7—N1117.74 (13)
C3—C2—H2120.8C9—C8—C7118.09 (15)
S1—C2—H2120.8C9—C8—C13120.84 (15)
C2—C3—C4103.3 (3)C7—C8—C13121.07 (14)
C2—C3—H3128.3C10—C9—C8120.92 (16)
C4—C3—H3128.3C10—C9—H9119.5
C1—C4—C3118.4 (5)C8—C9—H9119.5
C1—C4—H4120.8C11—C10—C9119.88 (16)
C3—C4—H4120.8C11—C10—H10120.1
C4'—C1'—C5132.7 (4)C9—C10—H10120.1
C4'—C1'—S1'108.1 (4)C10—C11—C12121.52 (16)
C5—C1'—S1'119.22 (13)C10—C11—H11119.2
C2'—S1'—C1'88.81 (14)C12—C11—H11119.2
C3'—C2'—S1'121.55 (19)C11—C12—C7117.44 (16)
C3'—C2'—H2'119.2C11—C12—C14120.33 (15)
S1'—C2'—H2'119.2C7—C12—C14122.21 (15)
C2'—C3'—C4'100.8 (4)C8—C13—H13A109.5
C2'—C3'—H3'129.6C8—C13—H13B109.5
C4'—C3'—H3'129.6H13A—C13—H13B109.5
C1'—C4'—C3'119.9 (6)C8—C13—H13C109.5
C1'—C4'—H4'120.1H13A—C13—H13C109.5
C3'—C4'—H4'120.1H13B—C13—H13C109.5
C1'—C5—C6110.43 (13)C12—C14—H14A109.5
C1—C5—C6110.43 (13)C12—C14—H14B109.5
C1'—C5—H5A109.6H14A—C14—H14B109.5
C1—C5—H5A109.6C12—C14—H14C109.5
C6—C5—H5A109.6H14A—C14—H14C109.5
C1'—C5—H5B109.6H14B—C14—H14C109.5
C1—C5—H5B109.6
C4—C1—S1—C20.1 (4)C7—N1—C6—C5179.66 (13)
C5—C1—S1—C2179.05 (14)C1—C5—C6—O176.75 (19)
C1—S1—C2—C34.17 (19)C1—C5—C6—N1101.88 (16)
S1—C2—C3—C46.2 (4)C6—N1—C7—C1264.1 (2)
C5—C1—C4—C3177.3 (3)C6—N1—C7—C8116.27 (17)
S1—C1—C4—C33.7 (6)C12—C7—C8—C90.9 (2)
C2—C3—C4—C16.3 (6)N1—C7—C8—C9179.47 (14)
C4'—C1'—S1'—C2'0.3 (4)C12—C7—C8—C13179.62 (15)
C5—C1'—S1'—C2'178.34 (14)N1—C7—C8—C130.0 (2)
C1'—S1'—C2'—C3'6.5 (2)C7—C8—C9—C101.3 (3)
S1'—C2'—C3'—C4'9.5 (4)C13—C8—C9—C10178.25 (16)
C5—C1'—C4'—C3'176.3 (3)C8—C9—C10—C111.9 (3)
S1'—C1'—C4'—C3'5.4 (7)C9—C10—C11—C120.4 (3)
C2'—C3'—C4'—C1'9.1 (7)C10—C11—C12—C71.6 (3)
C4'—C1'—C5—C6112.7 (5)C10—C11—C12—C14176.81 (17)
S1'—C1'—C5—C669.07 (18)C8—C7—C12—C112.3 (2)
C4—C1—C5—C678.1 (5)N1—C7—C12—C11178.09 (15)
S1—C1—C5—C6102.98 (15)C8—C7—C12—C14176.12 (16)
C7—N1—C6—O11.8 (2)N1—C7—C12—C143.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.882.042.8701 (18)157
C5—H5b···O1i0.992.383.2622 (19)148
Symmetry code: (i) x1, y, z.

Experimental details

Crystal data
Chemical formulaC14H15NOS
Mr245.34
Crystal system, space groupTriclinic, P1
Temperature (K)120
a, b, c (Å)4.7489 (2), 11.7309 (5), 11.8117 (4)
α, β, γ (°)100.981 (2), 95.427 (2), 101.104 (2)
V3)627.96 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.24
Crystal size (mm)0.16 × 0.06 × 0.02
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.896, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
11243, 2840, 2388
Rint0.043
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.121, 1.04
No. of reflections2840
No. of parameters175
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.27, 0.21

Computer programs: , DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.882.042.8701 (18)157
C5—H5b···O1i0.992.383.2622 (19)148
Symmetry code: (i) x1, y, z.
 

Footnotes

Additional correspondence author, e-mail: j.wardell@abdn.ac.uk.

Acknowledgements

The use of the EPSRC X-ray crystallographic service at the University of Southampton, England and the valuable assistance of the staff there is gratefully acknowledged. JLW acknowledges support from CAPES (Brazil).

References

First citationBrandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationCampaigne, E. (1984). In Comprehensive Heterocyclic Chemistry, Vol. 4, edited by A. R. Katritzky C. W. & Rees, pp. 863–934. Oxford: Pergamon.  Google Scholar
First citationHooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
First citationKleemann, A., Engel, J. B., Kutscher, B. & Reichert, D. (2006). Pharmaceutical Substances. New York, Stuttgart: Georg Thieme Verlag.  Google Scholar
First citationLourenço, M. C. S., Vicente, F. R., Henriques, M., das, G. M. de O., Candéa, A. L. P., Gonçalves, R. S. B., Nogueira, T. C. M., Ferreira, M. de L. & de Souza, M. V. N. (2007). Bioorg. Med. Chem. Lett. 17, 6895–6898.  PubMed Google Scholar
First citationOtwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.  Google Scholar
First citationSheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds