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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 9| September 2010| Page o2421
https://doi.org/10.1107/S1600536810033842

Ethyl 7-(4-bromo­phen­yl)-5-tri­fluoro­methyl-4,7-di­hydro­tetra­zolo[1,5-a]pyrimidine-6-carboxyl­ate

Shi-De Shen,a Xiao-Dong Feng,b,c Wei-Hua Yangb and Chang-Sheng Yaob,c*

aXuzhou Institute of Architectural Technology, Xuzhou 221116, People's Republic of China, bSchool of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou 221116, People's Republic of China, and cKey Laboratory of Biotechnology for Medicinal Plants, Xuzhou Normal University, Xuzhou 221116, People's Republic of China
*Correspondence e-mail: csyao@xznu.edu.cn

(Received 18 August 2010; accepted 22 August 2010; online 28 August 2010)

In the title compound, C14H11BrF3N5O2, the pyrimidine ring adopts a flattened envelope conformation with sp3-hybridized carbon as the flap [deviation = 0.177 (3) Å]. The dihedral angle between tetra­zole and bromo­phenyl rings is 84.3 (1)°. In the crystal, mol­ecules are linked into centrosymmetric dimers by pairs of N—H⋯N hydrogen bonds.

Related literature

For the biological activity of tetra­zolopyrimidine derivatives, see: Von Nussbaum et al. (2010[Von Nussbaum, F., Karthaus, D., Anlauf, S., Delbeck, M., Li, V. M., Meibom, D. & Lustig, K. (2010). WO Patent No. 2010078953.]); Abelman et al. (2009[Abelman, M., Jiang, R. & Zablocki, J. (2009). WO Patent No. 2009006580.]); Dougherty et al. (2007[Dougherty, A. M., Guo, H., Westby, G., Liu, Y., Simsek, E., Guo, J. T., Mehta, A., Norton, P., Gu, B., Block, T. & Cuconati, A. (2007). Antimicrob. Agents Chemother. 51, 4427-4437.]). For ring puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For the synthesis, see: Pryadeina et al. (2004[Pryadeina, M. V., Burgart, Ya. V., Saloutin, V. I., Kodess, M. I., Ulomskii, E. N. & Rusinov, V. L. (2004). Russ. J. Org. Chem. 40, 902-907.]).

[Scheme 1]

Experimental

Crystal data

  • C14H11BrF3N5O2

  • Mr = 418.19

  • Monoclinic, P 21 /c

  • a = 18.773 (2) Å

  • b = 10.4716 (11) Å

  • c = 7.8700 (8) Å

  • β = 92.27 (3)°

  • V = 1545.9 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 2.71 mm−1

  • T = 113 K

  • 0.32 × 0.28 × 0.18 mm
Data collection

  • Rigaku Saturn diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002[Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]) Tmin = 0.477, Tmax = 0.641

  • 18785 measured reflections

  • 3681 independent reflections

  • 2547 reflections with I > 2σ(I)

  • Rint = 0.065
Refinement

  • R[F2 > 2σ(F2)] = 0.030

  • wR(F2) = 0.071

  • S = 0.94

  • 3681 reflections

  • 231 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.43 e Å−3

  • Δρmin = −0.82 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1⋯N5i 0.83 (2) 2.06 (2) 2.862 (2) 163 (2)
Symmetry code: (i) -x, -y, -z.

Data collection: CrystalClear (Rigaku/MSC, 2002[Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810033842/ci5159sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810033842/ci5159Isup2.hkl

checkCIF report


Comment top

The tetrazolo[1,5-a]pyrimidine core represents an interesting pharmacophore with the feature of biological and pharmacological properties, which has human neutrophil elastase inhibitory (Von Nussbaum et al., 2010), late sodium channel blocker (Abelman et al., 2009) and hepatitis B virus surface antigen secretion inhibitory activities (Dougherty et al., 2007). This led us to pay much attention to the synthesis and bioactivity of compounds containing these two significant fragments. During the synthesis of trifluoromethylated tetrazolo[1,5-a]pyrimidine derivatives, the title compound was isolated and its structure was determined by X-ray analysis. The results are presented here.

In the title molecule (Fig.1), the tetrahydropyrimidine ring is in a flattened envelope conformation, with Cremer and Pople (1975) puckering parameters Q, θ, φ of 0.125 (2) Å, 109.7 (9)° and 11.7 (9)°, respectively; atom C2 deviates from the N1/N2/C1/C3/C4 plane (r.m.s. deviation 0.018 Å) by 0.177 (3) Å. The dihedral angle between N1/N2/C1/C3/C4 and C5-C10 planes [89.53 (3)°] shows that they are nearly perpendicular.

The crystal packing is stabilized by intermolecular N—H···N hydrogen bonds (Table 1 and Fig.2).

Related literature top

For the biological activity of tetrazolopyrimidine derivatives, see: Von Nussbaum et al. (2010); Abelman et al. (2009); Dougherty et al. (2007). For ring puckering parameters, see: Cremer & Pople (1975). For the synthesis, see: Pryadeina et al. (2004).

Experimental top

The title compound was synthesized according the procedure reported by Pryadeina et al.(2004). A mixture of ethyl 4,4,4-trifluoro-3-oxobutanoate (0.01 mol), 4-bromobenzaldehyde (0.01 mol) and 5-aminotetrazole (0.01 mol) in ethanol (20 ml) containing a catalytic amount of hydrochloric acid was heated for 12 h under reflux. Then the solvent was removed under reduced pressure. The residue was added to a solution of p-toluenesulfonic acid (0.05 g) in 100 mL of benzene, and the mixture was heated for 8 h with simultaneous removal of water as azeotrope with benzene. The solution was filtered while hot, the filtrate was evaporated, and the precipitate was recrystallized from ethanol. Cooling the ethanol solution slowly gave single crystals suitable for X-ray diffraction.

Refinement top

The N-bound H atom was located in a difference map and was refined freely [refined N–H length, 0.83 (2)Å]. All other H atoms were placed in calculated positions [C–H = 0.95–1.00 Å] and included in the final cycles of refinement using a riding model, with Uiso(H) = 1.2Ueq(parent atom).

Structure description top

The tetrazolo[1,5-a]pyrimidine core represents an interesting pharmacophore with the feature of biological and pharmacological properties, which has human neutrophil elastase inhibitory (Von Nussbaum et al., 2010), late sodium channel blocker (Abelman et al., 2009) and hepatitis B virus surface antigen secretion inhibitory activities (Dougherty et al., 2007). This led us to pay much attention to the synthesis and bioactivity of compounds containing these two significant fragments. During the synthesis of trifluoromethylated tetrazolo[1,5-a]pyrimidine derivatives, the title compound was isolated and its structure was determined by X-ray analysis. The results are presented here.

In the title molecule (Fig.1), the tetrahydropyrimidine ring is in a flattened envelope conformation, with Cremer and Pople (1975) puckering parameters Q, θ, φ of 0.125 (2) Å, 109.7 (9)° and 11.7 (9)°, respectively; atom C2 deviates from the N1/N2/C1/C3/C4 plane (r.m.s. deviation 0.018 Å) by 0.177 (3) Å. The dihedral angle between N1/N2/C1/C3/C4 and C5-C10 planes [89.53 (3)°] shows that they are nearly perpendicular.

The crystal packing is stabilized by intermolecular N—H···N hydrogen bonds (Table 1 and Fig.2).

For the biological activity of tetrazolopyrimidine derivatives, see: Von Nussbaum et al. (2010); Abelman et al. (2009); Dougherty et al. (2007). For ring puckering parameters, see: Cremer & Pople (1975). For the synthesis, see: Pryadeina et al. (2004).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2002); cell refinement: CrystalClear (Rigaku/MSC, 2002); data reduction: CrystalClear (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] Fig. 2. A packing diagram of the title compound. Intermolecular hydrogen bonds are shown as dashed lines.
Ethyl 7-(4-bromophenyl)-5-trifluoromethyl-4,7- dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate top
Crystal data top
C14H11BrF3N5O2F(000) = 832
Mr = 418.19Dx = 1.797 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4823 reflections
a = 18.773 (2) Åθ = 2.2–27.9°
b = 10.4716 (11) ŵ = 2.71 mm−1
c = 7.8700 (8) ÅT = 113 K
β = 92.27 (3)°Block, colourless
V = 1545.9 (3) Å30.32 × 0.28 × 0.18 mm
Z = 4
Data collection top
Rigaku Saturn
diffractometer		3681 independent reflections
Radiation source: rotating anode2547 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.065
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 2.2°
ω scansh = −24→24
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2002)		k = −13→13
Tmin = 0.477, Tmax = 0.641l = −10→10
18785 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)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071H atoms treated by a mixture of independent and constrained refinement
S = 0.94 w = 1/[σ2(Fo2) + (0.0321P)2]
where P = (Fo2 + 2Fc2)/3
3681 reflections(Δ/σ)max = 0.001
231 parametersΔρmax = 0.43 e Å−3
0 restraintsΔρmin = −0.82 e Å−3
Crystal data top
C14H11BrF3N5O2V = 1545.9 (3) Å3
Mr = 418.19Z = 4
Monoclinic, P21/cMo Kα radiation
a = 18.773 (2) ŵ = 2.71 mm−1
b = 10.4716 (11) ÅT = 113 K
c = 7.8700 (8) Å0.32 × 0.28 × 0.18 mm
β = 92.27 (3)°
Data collection top
Rigaku Saturn
diffractometer		3681 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2002)		2547 reflections with I > 2σ(I)
Tmin = 0.477, Tmax = 0.641Rint = 0.065
18785 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0300 restraints
wR(F2) = 0.071H atoms treated by a mixture of independent and constrained refinement
S = 0.94Δρmax = 0.43 e Å−3
3681 reflectionsΔρmin = −0.82 e Å−3
231 parameters
Special details top

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. 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 > 2sigma(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*/Ueq
Br10.468171 (12)0.24266 (2)−0.00430 (3)0.02485 (8)
F10.04617 (6)0.09175 (12)0.60550 (15)0.0283 (3)
F20.00359 (6)0.18117 (13)0.37917 (16)0.0312 (3)
F30.10127 (7)0.25030 (10)0.49390 (17)0.0279 (3)
H10.0275 (12)0.055 (2)0.176 (3)0.033 (7)*
N10.06837 (9)0.02879 (16)0.1959 (2)0.0142 (4)
N20.16300 (9)−0.09820 (15)0.1113 (2)0.0139 (4)
N30.17768 (9)−0.17880 (16)−0.0190 (2)0.0195 (4)
N40.12129 (9)−0.17855 (17)−0.1192 (2)0.0196 (4)
N50.06960 (9)−0.09971 (15)−0.0596 (2)0.0163 (4)
O10.18713 (8)0.08260 (14)0.67228 (18)0.0266 (4)
O20.27052 (7)−0.04022 (14)0.55633 (17)0.0209 (3)
C10.09759 (10)−0.05253 (18)0.0835 (2)0.0134 (4)
C20.21318 (10)−0.06715 (18)0.2535 (2)0.0143 (4)
H20.2315−0.14830.30620.017*
C30.17113 (10)0.00649 (18)0.3842 (2)0.0147 (4)
C40.10521 (11)0.05403 (18)0.3465 (2)0.0141 (4)
C50.27570 (10)0.00933 (19)0.1898 (2)0.0143 (4)
C60.26514 (11)0.12937 (19)0.1182 (3)0.0185 (5)
H60.21840.16420.10910.022*
C70.32231 (11)0.1991 (2)0.0599 (3)0.0187 (5)
H70.31500.28090.00970.022*
C80.39009 (11)0.14732 (19)0.0761 (2)0.0172 (5)
C90.40180 (11)0.02870 (19)0.1482 (3)0.0196 (5)
H90.4487−0.00540.15870.024*
C100.34446 (11)−0.03993 (19)0.2049 (3)0.0185 (5)
H100.3521−0.12160.25480.022*
C110.20751 (11)0.02294 (19)0.5533 (3)0.0174 (4)
C120.31205 (11)−0.0374 (2)0.7163 (3)0.0251 (5)
H12A0.2901−0.09330.80120.030*
H12B0.31450.05060.76200.030*
C130.38555 (12)−0.0847 (2)0.6780 (3)0.0290 (6)
H13A0.3820−0.17010.62760.043*
H13B0.4150−0.08840.78350.043*
H13C0.4074−0.02620.59790.043*
C140.06429 (11)0.1435 (2)0.4593 (3)0.0205 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.01555 (14)0.03165 (14)0.02782 (14)−0.00341 (9)0.00700 (9)0.00705 (10)
F10.0232 (8)0.0413 (8)0.0212 (7)−0.0037 (6)0.0114 (6)−0.0076 (6)
F20.0184 (7)0.0410 (8)0.0338 (8)0.0131 (6)−0.0035 (6)−0.0185 (7)
F30.0254 (8)0.0205 (7)0.0380 (8)−0.0022 (5)0.0034 (6)−0.0136 (6)
N10.0094 (10)0.0162 (9)0.0174 (9)0.0012 (7)0.0031 (7)−0.0026 (7)
N20.0110 (9)0.0147 (8)0.0163 (9)0.0004 (7)0.0036 (7)−0.0035 (7)
N30.0184 (10)0.0208 (10)0.0194 (9)0.0007 (8)0.0033 (8)−0.0074 (8)
N40.0152 (10)0.0220 (10)0.0218 (10)0.0018 (8)0.0027 (8)−0.0063 (8)
N50.0145 (10)0.0169 (9)0.0178 (9)0.0003 (7)0.0045 (7)−0.0036 (7)
O10.0224 (9)0.0357 (9)0.0217 (8)0.0044 (7)0.0022 (7)−0.0102 (7)
O20.0175 (8)0.0271 (8)0.0178 (8)0.0040 (6)−0.0011 (6)−0.0042 (6)
C10.0111 (11)0.0130 (9)0.0163 (10)−0.0016 (8)0.0050 (8)0.0019 (8)
C20.0122 (11)0.0140 (10)0.0167 (10)0.0005 (8)0.0012 (8)−0.0019 (8)
C30.0132 (11)0.0136 (9)0.0176 (10)−0.0029 (8)0.0051 (8)−0.0018 (8)
C40.0137 (11)0.0135 (10)0.0154 (10)−0.0030 (8)0.0058 (8)−0.0013 (8)
C50.0137 (11)0.0164 (10)0.0130 (10)−0.0005 (8)0.0038 (8)−0.0029 (8)
C60.0124 (12)0.0203 (11)0.0230 (11)0.0033 (9)0.0031 (9)0.0007 (9)
C70.0197 (12)0.0163 (10)0.0204 (11)0.0023 (9)0.0038 (9)0.0013 (9)
C80.0152 (12)0.0216 (11)0.0153 (10)−0.0036 (9)0.0052 (8)−0.0008 (9)
C90.0107 (11)0.0248 (12)0.0236 (12)0.0045 (9)0.0037 (9)0.0011 (9)
C100.0168 (12)0.0170 (10)0.0220 (11)0.0036 (9)0.0047 (9)0.0015 (9)
C110.0148 (12)0.0175 (10)0.0203 (11)−0.0032 (9)0.0037 (9)0.0003 (9)
C120.0193 (13)0.0366 (14)0.0192 (11)0.0028 (10)−0.0031 (9)0.0003 (10)
C130.0206 (13)0.0371 (14)0.0292 (13)0.0054 (11)−0.0004 (10)0.0039 (11)
C140.0142 (12)0.0238 (11)0.0235 (12)0.0006 (9)0.0014 (9)−0.0069 (10)
Geometric parameters (Å, º) top
Br1—C81.9025 (19)C3—C41.356 (3)
F1—C141.328 (2)C3—C111.482 (3)
F2—C141.340 (2)C4—C141.520 (3)
F3—C141.338 (2)C5—C61.388 (3)
N1—C11.359 (2)C5—C101.391 (3)
N1—C41.374 (3)C6—C71.392 (3)
N1—H10.83 (2)C6—H60.95
N2—C11.328 (2)C7—C81.385 (3)
N2—N31.365 (2)C7—H70.95
N2—C21.470 (2)C8—C91.379 (3)
N3—N41.295 (2)C9—C101.383 (3)
N4—N51.371 (2)C9—H90.95
N5—C11.320 (2)C10—H100.95
O1—C111.201 (2)C12—C131.508 (3)
O2—C111.355 (2)C12—H12A0.99
O2—C121.455 (2)C12—H12B0.99
C2—C51.522 (2)C13—H13A0.98
C2—C31.530 (3)C13—H13B0.98
C2—H21.00C13—H13C0.98
C1—N1—C4118.68 (17)C8—C7—H7120.6
C1—N1—H1119.1 (17)C6—C7—H7120.6
C4—N1—H1121.9 (16)C9—C8—C7121.45 (19)
C1—N2—N3108.16 (16)C9—C8—Br1119.80 (15)
C1—N2—C2127.32 (16)C7—C8—Br1118.75 (15)
N3—N2—C2124.50 (16)C8—C9—C10119.16 (19)
N4—N3—N2105.79 (16)C8—C9—H9120.4
N3—N4—N5111.43 (16)C10—C9—H9120.4
C1—N5—N4104.74 (16)C9—C10—C5120.74 (19)
C11—O2—C12116.29 (15)C9—C10—H10119.6
N5—C1—N2109.88 (17)C5—C10—H10119.6
N5—C1—N1129.27 (18)O1—C11—O2123.05 (19)
N2—C1—N1120.84 (18)O1—C11—C3127.68 (19)
N2—C2—C5110.17 (15)O2—C11—C3109.27 (17)
N2—C2—C3106.92 (15)O2—C12—C13106.47 (17)
C5—C2—C3112.42 (16)O2—C12—H12A110.4
N2—C2—H2109.1C13—C12—H12A110.4
C5—C2—H2109.1O2—C12—H12B110.4
C3—C2—H2109.1C13—C12—H12B110.4
C4—C3—C11122.55 (18)H12A—C12—H12B108.6
C4—C3—C2121.92 (18)C12—C13—H13A109.5
C11—C3—C2115.53 (17)C12—C13—H13B109.5
C3—C4—N1122.81 (17)H13A—C13—H13B109.5
C3—C4—C14125.21 (18)C12—C13—H13C109.5
N1—C4—C14111.95 (17)H13A—C13—H13C109.5
C6—C5—C10119.19 (18)H13B—C13—H13C109.5
C6—C5—C2120.69 (18)F1—C14—F3108.26 (17)
C10—C5—C2120.11 (18)F1—C14—F2106.58 (17)
C5—C6—C7120.64 (19)F3—C14—F2105.95 (17)
C5—C6—H6119.7F1—C14—C4114.01 (17)
C7—C6—H6119.7F3—C14—C4111.34 (17)
C8—C7—C6118.80 (19)F2—C14—C4110.28 (17)
C1—N2—N3—N40.1 (2)C3—C2—C5—C6−55.7 (2)
C2—N2—N3—N4−178.49 (17)N2—C2—C5—C10−117.49 (19)
N2—N3—N4—N50.2 (2)C3—C2—C5—C10123.4 (2)
N3—N4—N5—C1−0.4 (2)C10—C5—C6—C71.0 (3)
N4—N5—C1—N20.4 (2)C2—C5—C6—C7−179.92 (18)
N4—N5—C1—N1−178.44 (19)C5—C6—C7—C8−0.7 (3)
N3—N2—C1—N5−0.3 (2)C6—C7—C8—C90.2 (3)
C2—N2—C1—N5178.17 (17)C6—C7—C8—Br1179.84 (15)
N3—N2—C1—N1178.65 (16)C7—C8—C9—C100.2 (3)
C2—N2—C1—N1−2.8 (3)Br1—C8—C9—C10−179.52 (15)
C4—N1—C1—N5172.99 (19)C8—C9—C10—C50.1 (3)
C4—N1—C1—N2−5.8 (3)C6—C5—C10—C9−0.7 (3)
C1—N2—C2—C5−111.0 (2)C2—C5—C10—C9−179.76 (18)
N3—N2—C2—C567.3 (2)C12—O2—C11—O12.7 (3)
C1—N2—C2—C311.5 (2)C12—O2—C11—C3−177.93 (16)
N3—N2—C2—C3−170.26 (16)C4—C3—C11—O1−4.0 (3)
N2—C2—C3—C4−13.1 (2)C2—C3—C11—O1175.58 (19)
C5—C2—C3—C4108.0 (2)C4—C3—C11—O2176.71 (17)
N2—C2—C3—C11167.39 (16)C2—C3—C11—O2−3.7 (2)
C5—C2—C3—C11−71.6 (2)C11—O2—C12—C13−166.71 (17)
C11—C3—C4—N1−173.55 (17)C3—C4—C14—F1−65.4 (3)
C2—C3—C4—N16.9 (3)N1—C4—C14—F1116.58 (19)
C11—C3—C4—C148.6 (3)C3—C4—C14—F357.5 (3)
C2—C3—C4—C14−170.92 (18)N1—C4—C14—F3−120.58 (19)
C1—N1—C4—C33.5 (3)C3—C4—C14—F2174.78 (18)
C1—N1—C4—C14−178.41 (17)N1—C4—C14—F2−3.3 (2)
N2—C2—C5—C663.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N5i0.83 (2)2.06 (2)2.862 (2)163 (2)
Symmetry code: (i) −x, −y, −z.

Experimental details

Crystal data
Chemical formulaC14H11BrF3N5O2
Mr418.19
Crystal system, space groupMonoclinic, P21/c
Temperature (K)113
a, b, c (Å)18.773 (2), 10.4716 (11), 7.8700 (8)
β (°) 92.27 (3)
V (Å3)1545.9 (3)
Z4
Radiation typeMo Kα
µ (mm−1)2.71
Crystal size (mm)0.32 × 0.28 × 0.18
Data collection
DiffractometerRigaku Saturn
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2002)
Tmin, Tmax0.477, 0.641
No. of measured, independent and
observed [I > 2σ(I)] reflections		18785, 3681, 2547
Rint0.065
(sin θ/λ)max (Å−1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.071, 0.94
No. of reflections3681
No. of parameters231
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.43, −0.82

Computer programs: CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N5i0.83 (2)2.06 (2)2.862 (2)163 (2)
Symmetry code: (i) −x, −y, −z.
 

Acknowledgements

The authors are grateful for financial support from the Major Basic Research Project of the Natural Science Foundation of Jiangsu Higher Education Institutions (No. 09 KJ A430003), the Natural Science Foundation of Xuzhou City (No. XM09B016), the Graduate Foundation of Xuzhou Normal University (No. 2010YLB029) and the Qing Lan Project (No. 08QLT001).

References

First citationAbelman, M., Jiang, R. & Zablocki, J. (2009). WO Patent No. 2009006580.  Google Scholar
 First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science Google Scholar
 First citationDougherty, A. M., Guo, H., Westby, G., Liu, Y., Simsek, E., Guo, J. T., Mehta, A., Norton, P., Gu, B., Block, T. & Cuconati, A. (2007). Antimicrob. Agents Chemother. 51, 4427–4437.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationPryadeina, M. V., Burgart, Ya. V., Saloutin, V. I., Kodess, M. I., Ulomskii, E. N. & Rusinov, V. L. (2004). Russ. J. Org. Chem. 40, 902–907.  Web of Science CrossRef CAS Google Scholar
 First citationRigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationVon Nussbaum, F., Karthaus, D., Anlauf, S., Delbeck, M., Li, V. M., Meibom, D. & Lustig, K. (2010). WO Patent No. 2010078953.  Google Scholar

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ISSN: 2056-9890
Volume 66| Part 9| September 2010| Page o2421
https://doi.org/10.1107/S1600536810033842
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