5-Benzoyl-4-hydr­oxy-6-(4-nitro­phen­yl)-4-trifluoro­meth­yl-3,4,5,6-tetrahydro­pyrimidin-2(1H)-one monohydrate

Yang, F.-L.; Zhang, J.; Yao, C.-S.

doi:10.1107/S160053680804124X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Pages o87-o88

doi:10.1107/S160053680804124X

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5-Benzoyl-4-hydroxy-6-(4-nitrophenyl)-4-trifluoromethyl-3,4,5,6-tetrahydropyrimidin-2(1H)-one monohydrate

Feng-Ling Yang,^a ^* Jing Zhang ^b and Chang-Sheng Yao ^c,^d

^aCollege of Chemistry and Chemical Engineering, Xuchang University, Xuchang, Henan Province 461000, People's Republic of China, ^bLuohe Medical College, Luohe, Henan Province 462002, People's Republic of China, ^cSchool of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou 221116, People's Republic of China, and ^dKey Laboratory of Biotechnology for Medicinal Plants, Xuzhou Normal University, Xuzhou 221116, People's Republic of China
^*Correspondence e-mail: Actaeli@gmail.com

(Received 18 November 2008; accepted 6 December 2008; online 10 December 2008)

The asymmetric unit of the title compound, C₁₈H₁₄F₃N₃O₅·H₂O, contains two independent formula units. The two heterocyclic molecules differ in the orientations of the benzoylphenyl group with respect to the tetrahydropyrimidine ring [C—C—C—C torsion angles of 64.5 (3) and 67.1 (3)°]. In both molecules the pyrimidine ring adopts a half-chair conformation. The molecules are linked into a two-dimensional network parallel to (001) by N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For the bioactivity of dihydropyrimidines, see: Brier et al. (2004 ); Cochran et al. (2005 ); Moran et al. (2007 ); Zorkun et al. (2006 ). For the bioactivity of organofluorine compounds, see: Hermann et al. (2003 ); Ulrich (2004 ).

Experimental

Crystal data

C₁₈H₁₄F₃N₃O₅·H₂O
M_r = 427.34
Orthorhombic, P n a 2₁
a = 14.389 (3) Å
b = 9.0391 (18) Å
c = 28.141 (6) Å
V = 3660.1 (13) Å³
Z = 8
Mo Kα radiation
μ = 0.14 mm⁻¹
T = 113 (2) K
0.32 × 0.22 × 0.20 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear, Rigaku/MSC, 2002 ) T_min = 0.958, T_max = 0.973
28524 measured reflections
4437 independent reflections
4222 reflections with I > 2σ(I)
R_int = 0.059

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.107
S = 1.06
4437 reflections
575 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O11	0.92 (4)	2.11 (4)	2.903 (3)	144 (3)
N1—H1⋯O11ⁱ	0.95 (3)	2.08 (4)	3.011 (3)	167 (3)
N5—H5⋯O12ⁱⁱ	0.89 (4)	2.05 (4)	2.907 (3)	163 (3)
N4—H4⋯O12ⁱⁱⁱ	0.85 (4)	2.17 (4)	3.019 (3)	176 (3)
O5—H5A⋯O6^iv	0.89 (4)	1.78 (4)	2.678 (3)	178 (4)
O10—H10A⋯O1^v	0.85 (2)	1.82 (2)	2.672 (3)	178 (4)
O12—H12A⋯O5	0.85 (4)	2.13 (4)	2.817 (3)	137 (3)
O12—H12A⋯O2	0.85 (4)	2.32 (4)	3.026 (3)	140 (3)
O11—H11A⋯O10^vi	0.82 (4)	2.22 (4)	2.815 (3)	129 (3)
O11—H11A⋯O7^vi	0.82 (4)	2.27 (4)	3.009 (3)	150 (3)
O11—H11B⋯O6^vii	0.83 (4)	2.05 (4)	2.853 (3)	163 (4)
O12—H12B⋯O1^viii	0.82 (4)	2.12 (4)	2.840 (3)	147 (3)
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x, -y+2, z+{\script{1\over 2}}]$ ; (iv) $[-x, -y+2, z-{\script{1\over 2}}]$ ; (v) $[-x, -y+1, z+{\script{1\over 2}}]$ ; (vi) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (vii) $[-x+{\script{1\over 2}}, y-{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (viii) x, y+1, z.

Data collection: CrystalClear (Rigaku/MSC, 2002); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680804124X/ci2728sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680804124X/ci2728Isup2.hkl

checkCIF report

Comment top

Dihydropyrimidine (DHPM) derivatives can be used as potential calcium channel blockers (Zorkun et al., 2006), inhibitors of mitotic kinesin Eg5 for treating cancer (Cochran et al., 2005; Brier et al., 2004) and as TRPA1 modulators for treating pain (Moran et al., 2007). Besides, compounds that contain fluorine have special bioactivity, for example, flumioxazin is a widely used herbicide (Hermann et al., 2003; Ulrich,2004). This led us to pay much attention to the synthesis and bioactivity of these important fused perfluoroalkylated heterocyclic compounds. During the synthesis of DHPM derivatives, the title compound, an intermediate, was isolated and confirmed by X-ray diffraction to elucidate the reaction mechanism. We report here the crystal structure of the title compound.

The asymmetric unit of the title compound (Fig.1) contains two independent molecules which differ in the orientations of benzoylphenyl group with respect to the tetrahydropyrimidine ring. In both molecules, the pyrimidine ring adopts a half-chair conformation. The bulky substituents on the heterocyclic ring are in trans position, which must be attributed to the steric effect. The dihedral angles between C5-C10 and C12-C17 phenyl rings is 60.0 (1)° and that between C23-C28 and C30-C35 rings is 65.2 (1)°.

The crystal packing shows that the molecules are linked into a two-dimensional network parallel to the (001) by N—H···O and O—H···O hydrogen bonds (Table 1 and Fig. 2).

Related literature top

For the bioactivity of dihydropyrimidines, see: Brier et al. (2004); Cochran et al. (2005); Moran et al. (2007); Zorkun et al. (2006). For the bioactivity of organofluorine compounds, see: Hermann et al. (2003); Ulrich (2004).

Experimental top

The title compound was synthesized by the reaction of 4-nitro-benzaldehyde (1 mmol), 4,4,4-trifluoro-1-phenylbutane-1,3-dione (1 mmol) and urea (1 mmol), catalyzed by 4-methylbenzenesulfonic acid, at 363 K for a certain time (monitered by TLC). After cooling, the reaction mixture was washed with water and recrystallized from ethanol, to obtain single crystals suitable for X-ray diffraction.

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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. Hydrogen bonds are shown as dashed lines.
	Fig. 2. The packing diagram of the title compound. Intermolecular hydrogen bonds are shown as dashed lines.

5-Benzoyl-4-hydroxy-6-(4-nitrophenyl)-4-trifluoromethyl-3,4,5,6- tetrahydropyrimidin-2(1H)-one monohydrate top

Crystal data top

C₁₈H₁₄F₃N₃O₅·H₂O	F(000) = 1760
M_r = 427.34	D_x = 1.551 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 6634 reflections
a = 14.389 (3) Å	θ = 2.6–25.0°
b = 9.0391 (18) Å	µ = 0.14 mm⁻¹
c = 28.141 (6) Å	T = 113 K
V = 3660.1 (13) Å³	Prism, colourless
Z = 8	0.32 × 0.22 × 0.20 mm

Data collection top

Rigaku Saturn diffractometer	4437 independent reflections
Radiation source: rotating anode	4222 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.059
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.9°, θ_min = 2.4°
ω scans	h = −18→18
Absorption correction: multi-scan (CrystalClear, Rigaku/MSC, 2002)	k = −11→10
T_min = 0.958, T_max = 0.973	l = −36→37
28524 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0683P)² + 0.2165P] where P = (F_o² + 2F_c²)/3
4437 reflections	(Δ/σ)_max = 0.044
575 parameters	Δρ_max = 0.25 e Å⁻³
2 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₈H₁₄F₃N₃O₅·H₂O	V = 3660.1 (13) Å³
M_r = 427.34	Z = 8
Orthorhombic, Pna2₁	Mo Kα radiation
a = 14.389 (3) Å	µ = 0.14 mm⁻¹
b = 9.0391 (18) Å	T = 113 K
c = 28.141 (6) Å	0.32 × 0.22 × 0.20 mm

Data collection top

Rigaku Saturn diffractometer	4437 independent reflections
Absorption correction: multi-scan (CrystalClear, Rigaku/MSC, 2002)	4222 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.973	R_int = 0.059
28524 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	2 restraints
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.25 e Å⁻³
4437 reflections	Δρ_min = −0.31 e Å⁻³
575 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

	x	y	z	U_iso*/U_eq
N1	−0.09671 (16)	0.3614 (2)	0.59693 (8)	0.0172 (4)
H1	−0.158 (2)	0.351 (3)	0.5850 (13)	0.022 (8)*
N2	0.05590 (16)	0.2777 (3)	0.59022 (9)	0.0212 (5)
H2A	0.088 (3)	0.198 (4)	0.5786 (14)	0.032 (10)*
N3	0.40154 (18)	0.2937 (3)	0.73426 (9)	0.0275 (5)
N4	0.17052 (16)	1.1349 (2)	0.98405 (8)	0.0163 (4)
H4	0.117 (2)	1.137 (3)	0.9964 (13)	0.021 (8)*
N5	0.32327 (15)	1.2159 (3)	0.99252 (9)	0.0205 (5)
H5	0.364 (3)	1.277 (4)	1.0061 (14)	0.033 (9)*
N6	0.66618 (17)	1.2226 (3)	0.84793 (9)	0.0246 (5)
O1	−0.06318 (13)	0.1373 (2)	0.56457 (7)	0.0213 (4)
O2	0.09085 (15)	0.7349 (2)	0.62345 (8)	0.0281 (5)
O3	0.38832 (18)	0.2127 (3)	0.76856 (9)	0.0419 (6)
O4	0.47761 (17)	0.3480 (3)	0.72524 (11)	0.0509 (7)
O5	−0.04878 (14)	0.5953 (2)	0.56735 (7)	0.0196 (4)
H5A	−0.101 (3)	0.613 (4)	0.5511 (14)	0.029*
O6	0.20406 (14)	1.35887 (19)	1.01700 (7)	0.0207 (4)
O7	0.36076 (15)	0.7632 (2)	0.95958 (8)	0.0262 (4)
O8	0.64950 (18)	1.2982 (3)	0.81335 (9)	0.0431 (6)
O9	0.74415 (16)	1.1810 (3)	0.85877 (10)	0.0427 (6)
O10	0.21816 (13)	0.9012 (2)	1.01373 (7)	0.0205 (4)
H10A	0.1681 (18)	0.889 (4)	1.0294 (13)	0.031*
C1	−0.03449 (18)	0.2551 (3)	0.58280 (10)	0.0172 (5)
C2	0.09768 (18)	0.4139 (3)	0.60829 (9)	0.0175 (5)
H2	0.1185	0.4770	0.5811	0.021*
C3	0.02400 (17)	0.4968 (3)	0.63747 (9)	0.0164 (5)
H3	0.0100	0.4373	0.6666	0.020*
C4	−0.06557 (18)	0.5103 (3)	0.60803 (9)	0.0155 (5)
C5	0.17991 (18)	0.3796 (3)	0.64030 (9)	0.0180 (5)
C6	0.17091 (19)	0.2707 (3)	0.67560 (11)	0.0227 (6)
H6	0.1153	0.2144	0.6777	0.027*
C7	0.2428 (2)	0.2452 (3)	0.70731 (10)	0.0229 (6)
H7	0.2368	0.1733	0.7317	0.027*
C8	0.32376 (19)	0.3271 (3)	0.70250 (10)	0.0200 (5)
C9	0.33499 (19)	0.4337 (3)	0.66753 (10)	0.0224 (6)
H9	0.3915	0.4873	0.6648	0.027*
C10	0.26174 (19)	0.4602 (3)	0.63676 (10)	0.0207 (5)
H10	0.2676	0.5342	0.6130	0.025*
C11	0.06423 (19)	0.6473 (3)	0.65320 (10)	0.0191 (5)
C12	0.0703 (2)	0.6817 (3)	0.70501 (11)	0.0228 (6)
C13	0.0605 (2)	0.5753 (3)	0.74055 (11)	0.0296 (6)
H13	0.0485	0.4751	0.7324	0.036*
C14	0.0685 (3)	0.6161 (4)	0.78780 (13)	0.0411 (8)
H14	0.0626	0.5434	0.8120	0.049*
C15	0.0846 (3)	0.7598 (5)	0.79987 (15)	0.0499 (10)
H15	0.0898	0.7863	0.8324	0.060*
C16	0.0935 (3)	0.8662 (4)	0.76563 (17)	0.0517 (11)
H16	0.1037	0.9663	0.7745	0.062*
C17	0.0875 (3)	0.8281 (4)	0.71771 (14)	0.0361 (8)
H17	0.0950	0.9016	0.6939	0.043*
C18	−0.14246 (19)	0.5841 (3)	0.63835 (10)	0.0194 (5)
C19	0.23177 (18)	1.2409 (3)	0.99904 (10)	0.0169 (5)
C20	0.36507 (18)	1.0817 (3)	0.97328 (10)	0.0189 (5)
H20	0.3873	1.0176	0.9999	0.023*
C21	0.29152 (17)	0.9978 (3)	0.94407 (9)	0.0161 (5)
H21	0.2781	1.0563	0.9147	0.019*
C22	0.20117 (18)	0.9860 (3)	0.97330 (9)	0.0174 (5)
C23	0.44638 (18)	1.1209 (3)	0.94105 (10)	0.0177 (5)
C24	0.43558 (19)	1.2302 (3)	0.90652 (11)	0.0230 (6)
H24	0.3790	1.2840	0.9047	0.028*
C25	0.5063 (2)	1.2605 (3)	0.87512 (11)	0.0231 (6)
H25	0.4986	1.3324	0.8508	0.028*
C26	0.58888 (18)	1.1836 (3)	0.87981 (10)	0.0194 (5)
C27	0.60266 (19)	1.0753 (3)	0.91366 (10)	0.0206 (5)
H27	0.6603	1.0247	0.9161	0.025*
C28	0.52921 (19)	1.0424 (3)	0.94424 (10)	0.0199 (5)
H28	0.5358	0.9663	0.9673	0.024*
C29	0.33101 (19)	0.8468 (3)	0.92912 (10)	0.0200 (5)
C30	0.3331 (2)	0.8049 (3)	0.87787 (11)	0.0238 (6)
C31	0.3250 (2)	0.9069 (3)	0.84102 (11)	0.0274 (6)
H31	0.3171	1.0090	0.8480	0.033*
C32	0.3284 (3)	0.8593 (4)	0.79407 (12)	0.0364 (8)
H32	0.3237	0.9292	0.7690	0.044*
C33	0.3385 (3)	0.7107 (4)	0.78375 (14)	0.0444 (9)
H33	0.3397	0.6785	0.7516	0.053*
C34	0.3470 (3)	0.6092 (4)	0.82007 (14)	0.0429 (9)
H34	0.3544	0.5072	0.8128	0.052*
C35	0.3447 (3)	0.6548 (3)	0.86693 (12)	0.0329 (7)
H35	0.3509	0.5843	0.8918	0.040*
C36	0.1248 (2)	0.9125 (3)	0.94281 (10)	0.0210 (5)
F1	−0.14776 (12)	0.52363 (19)	0.68178 (6)	0.0286 (4)
F2	−0.22576 (11)	0.57373 (19)	0.61866 (6)	0.0274 (4)
F3	−0.12376 (13)	0.72802 (19)	0.64456 (7)	0.0324 (4)
F4	0.04104 (12)	0.92471 (19)	0.96255 (6)	0.0280 (4)
F5	0.12020 (12)	0.97358 (19)	0.89937 (6)	0.0278 (4)
F6	0.14278 (13)	0.76842 (18)	0.93679 (8)	0.0322 (4)
O11	0.21603 (13)	0.1296 (2)	0.54929 (8)	0.0212 (4)
H11A	0.215 (3)	0.183 (4)	0.5257 (15)	0.032*
H11B	0.228 (3)	0.046 (4)	0.5390 (14)	0.032*
O12	0.01675 (13)	0.8681 (2)	0.53237 (8)	0.0213 (4)
H12A	0.012 (2)	0.807 (4)	0.5554 (15)	0.032*
H12B	0.015 (3)	0.948 (4)	0.5459 (14)	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0173 (11)	0.0159 (10)	0.0185 (10)	−0.0003 (8)	−0.0023 (9)	−0.0037 (8)
N2	0.0182 (11)	0.0221 (12)	0.0233 (12)	0.0018 (9)	−0.0025 (9)	−0.0082 (9)
N3	0.0243 (12)	0.0319 (13)	0.0263 (13)	0.0078 (10)	−0.0046 (10)	−0.0066 (11)
N4	0.0139 (11)	0.0149 (10)	0.0200 (11)	0.0003 (8)	0.0022 (9)	−0.0035 (8)
N5	0.0146 (10)	0.0204 (11)	0.0265 (13)	−0.0035 (8)	0.0029 (9)	−0.0085 (10)
N6	0.0225 (12)	0.0256 (11)	0.0257 (13)	−0.0043 (9)	0.0055 (10)	−0.0005 (10)
O1	0.0200 (9)	0.0186 (9)	0.0254 (10)	0.0006 (7)	−0.0051 (8)	−0.0064 (7)
O2	0.0314 (11)	0.0223 (9)	0.0306 (12)	−0.0066 (8)	−0.0053 (9)	0.0047 (8)
O3	0.0397 (14)	0.0552 (15)	0.0309 (13)	0.0083 (11)	−0.0100 (10)	0.0120 (12)
O4	0.0212 (12)	0.0774 (19)	0.0542 (17)	−0.0049 (12)	−0.0122 (11)	0.0189 (15)
O5	0.0198 (10)	0.0227 (9)	0.0162 (9)	−0.0035 (7)	−0.0041 (7)	0.0070 (7)
O6	0.0205 (10)	0.0172 (9)	0.0246 (10)	−0.0014 (7)	0.0049 (8)	−0.0074 (7)
O7	0.0313 (11)	0.0257 (10)	0.0217 (11)	0.0099 (9)	0.0031 (8)	0.0039 (8)
O8	0.0383 (14)	0.0547 (15)	0.0363 (14)	0.0066 (11)	0.0154 (11)	0.0214 (13)
O9	0.0190 (11)	0.0639 (16)	0.0453 (14)	0.0005 (11)	0.0045 (10)	0.0152 (12)
O10	0.0176 (10)	0.0233 (9)	0.0206 (9)	0.0010 (7)	0.0033 (7)	0.0070 (8)
C1	0.0186 (12)	0.0169 (12)	0.0161 (13)	0.0005 (10)	−0.0019 (10)	−0.0006 (9)
C2	0.0157 (12)	0.0177 (11)	0.0191 (12)	−0.0010 (9)	0.0000 (9)	−0.0006 (9)
C3	0.0161 (12)	0.0171 (11)	0.0159 (11)	−0.0010 (9)	−0.0020 (9)	−0.0005 (9)
C4	0.0163 (12)	0.0152 (11)	0.0150 (11)	0.0005 (9)	−0.0020 (9)	0.0003 (9)
C5	0.0179 (13)	0.0175 (12)	0.0187 (12)	0.0005 (9)	−0.0014 (10)	−0.0027 (9)
C6	0.0165 (12)	0.0248 (13)	0.0267 (15)	−0.0027 (10)	−0.0009 (11)	0.0028 (11)
C7	0.0249 (14)	0.0238 (13)	0.0200 (15)	0.0072 (11)	0.0004 (11)	0.0026 (10)
C8	0.0166 (13)	0.0243 (12)	0.0192 (12)	0.0052 (10)	−0.0033 (10)	−0.0051 (10)
C9	0.0163 (12)	0.0233 (13)	0.0277 (15)	−0.0012 (10)	−0.0008 (11)	−0.0038 (11)
C10	0.0206 (13)	0.0204 (12)	0.0210 (13)	−0.0002 (10)	−0.0011 (10)	0.0003 (10)
C11	0.0172 (12)	0.0166 (12)	0.0234 (13)	−0.0005 (9)	−0.0063 (10)	−0.0005 (10)
C12	0.0225 (13)	0.0210 (13)	0.0249 (14)	0.0008 (10)	−0.0059 (11)	−0.0067 (11)
C13	0.0373 (17)	0.0302 (15)	0.0214 (14)	0.0032 (12)	−0.0072 (12)	−0.0052 (12)
C14	0.050 (2)	0.050 (2)	0.0231 (16)	0.0086 (17)	−0.0084 (15)	−0.0097 (15)
C15	0.059 (3)	0.064 (2)	0.0273 (19)	0.001 (2)	−0.0115 (17)	−0.0219 (18)
C16	0.057 (2)	0.042 (2)	0.056 (3)	−0.0058 (17)	−0.011 (2)	−0.032 (2)
C17	0.0393 (19)	0.0251 (15)	0.044 (2)	−0.0038 (13)	−0.0058 (15)	−0.0093 (14)
C18	0.0193 (13)	0.0186 (12)	0.0202 (13)	−0.0016 (10)	−0.0013 (10)	−0.0007 (10)
C19	0.0183 (12)	0.0168 (12)	0.0156 (12)	−0.0015 (10)	0.0018 (10)	−0.0011 (9)
C20	0.0171 (12)	0.0204 (12)	0.0193 (12)	0.0002 (9)	0.0039 (10)	−0.0011 (10)
C21	0.0159 (12)	0.0148 (11)	0.0174 (12)	−0.0002 (9)	0.0012 (9)	0.0012 (9)
C22	0.0192 (12)	0.0151 (11)	0.0178 (12)	−0.0001 (9)	0.0020 (9)	0.0005 (9)
C23	0.0154 (13)	0.0187 (12)	0.0191 (12)	−0.0017 (9)	0.0004 (10)	−0.0034 (10)
C24	0.0160 (12)	0.0257 (13)	0.0272 (15)	0.0000 (10)	−0.0012 (11)	0.0025 (11)
C25	0.0219 (13)	0.0239 (13)	0.0234 (15)	0.0018 (11)	−0.0005 (11)	0.0047 (11)
C26	0.0170 (13)	0.0221 (12)	0.0193 (12)	−0.0040 (9)	0.0022 (10)	−0.0016 (10)
C27	0.0193 (13)	0.0193 (12)	0.0231 (14)	0.0012 (10)	0.0014 (10)	−0.0004 (10)
C28	0.0199 (13)	0.0202 (12)	0.0196 (12)	0.0012 (10)	−0.0013 (10)	−0.0012 (10)
C29	0.0169 (13)	0.0201 (13)	0.0231 (14)	−0.0009 (10)	0.0038 (10)	−0.0012 (10)
C30	0.0224 (14)	0.0258 (14)	0.0233 (14)	0.0005 (11)	0.0076 (11)	−0.0031 (11)
C31	0.0305 (16)	0.0267 (14)	0.0249 (15)	0.0002 (12)	0.0049 (12)	−0.0012 (12)
C32	0.0425 (19)	0.0447 (19)	0.0221 (16)	0.0049 (15)	0.0058 (14)	−0.0001 (14)
C33	0.055 (2)	0.053 (2)	0.0260 (18)	0.0000 (17)	0.0102 (16)	−0.0170 (16)
C34	0.063 (3)	0.0310 (16)	0.0350 (18)	0.0015 (16)	0.0148 (17)	−0.0141 (14)
C35	0.0451 (19)	0.0243 (14)	0.0294 (17)	0.0044 (13)	0.0100 (14)	−0.0068 (12)
C36	0.0214 (14)	0.0177 (12)	0.0238 (13)	−0.0017 (10)	0.0015 (11)	−0.0021 (10)
F1	0.0313 (9)	0.0361 (9)	0.0182 (8)	0.0027 (7)	0.0060 (7)	0.0003 (7)
F2	0.0177 (8)	0.0352 (9)	0.0293 (9)	0.0046 (7)	−0.0009 (7)	−0.0078 (7)
F3	0.0316 (10)	0.0180 (8)	0.0475 (13)	0.0040 (7)	0.0041 (8)	−0.0103 (8)
F4	0.0183 (8)	0.0348 (9)	0.0310 (9)	−0.0038 (7)	0.0037 (7)	−0.0104 (8)
F5	0.0300 (9)	0.0331 (9)	0.0202 (8)	−0.0026 (7)	−0.0041 (7)	−0.0016 (7)
F6	0.0328 (10)	0.0178 (8)	0.0459 (12)	−0.0009 (7)	−0.0003 (8)	−0.0105 (8)
O11	0.0228 (10)	0.0166 (9)	0.0242 (10)	0.0021 (8)	−0.0009 (8)	0.0028 (8)
O12	0.0242 (11)	0.0171 (9)	0.0224 (10)	0.0020 (7)	0.0009 (8)	0.0011 (8)

Geometric parameters (Å, º) top

N1—C1	1.372 (3)	C13—H13	0.95
N1—C4	1.452 (3)	C14—C15	1.362 (6)
N1—H1	0.95 (3)	C14—H14	0.95
N2—C1	1.333 (3)	C15—C16	1.367 (7)
N2—C2	1.461 (3)	C15—H15	0.95
N2—H2A	0.92 (4)	C16—C17	1.395 (6)
N3—O4	1.226 (4)	C16—H16	0.95
N3—O3	1.226 (4)	C17—H17	0.95
N3—C8	1.464 (3)	C18—F2	1.324 (3)
N4—C19	1.368 (3)	C18—F3	1.340 (3)
N4—C22	1.449 (3)	C18—F1	1.341 (3)
N4—H4	0.85 (4)	C20—C23	1.522 (4)
N5—C19	1.348 (3)	C20—C21	1.540 (4)
N5—C20	1.458 (3)	C20—H20	1.00
N5—H5	0.89 (4)	C21—C29	1.537 (4)
N6—O8	1.213 (4)	C21—C22	1.542 (3)
N6—O9	1.222 (3)	C21—H21	1.00
N6—C26	1.472 (3)	C22—C36	1.545 (4)
O1—C1	1.252 (3)	C23—C28	1.390 (4)
O2—C11	1.214 (4)	C23—C24	1.394 (4)
O5—C4	1.400 (3)	C24—C25	1.375 (4)
O5—H5A	0.89 (4)	C24—H24	0.95
O6—C19	1.246 (3)	C25—C26	1.383 (4)
O7—C29	1.221 (3)	C25—H25	0.95
O10—C22	1.393 (3)	C26—C27	1.380 (4)
O10—H10A	0.852 (19)	C27—C28	1.395 (4)
C2—C5	1.519 (4)	C27—H27	0.95
C2—C3	1.536 (4)	C28—H28	0.95
C2—H2	1.00	C29—C30	1.491 (4)
C3—C4	1.537 (3)	C30—C31	1.393 (4)
C3—C11	1.544 (4)	C30—C35	1.401 (4)
C3—H3	1.00	C31—C32	1.390 (4)
C4—C18	1.548 (4)	C31—H31	0.95
C5—C10	1.388 (4)	C32—C33	1.382 (5)
C5—C6	1.405 (4)	C32—H32	0.95
C6—C7	1.385 (4)	C33—C34	1.379 (6)
C6—H6	0.95	C33—H33	0.95
C7—C8	1.387 (4)	C34—C35	1.382 (5)
C7—H7	0.95	C34—H34	0.95
C8—C9	1.387 (4)	C35—H35	0.95
C9—C10	1.385 (4)	C36—F4	1.331 (3)
C9—H9	0.95	C36—F6	1.338 (3)
C10—H10	0.95	C36—F5	1.343 (3)
C11—C12	1.493 (4)	O11—H11A	0.82 (4)
C12—C17	1.393 (4)	O11—H11B	0.83 (4)
C12—C13	1.395 (4)	O12—H12A	0.85 (4)
C13—C14	1.385 (4)	O12—H12B	0.82 (4)

C1—N1—C4	120.7 (2)	C12—C17—C16	119.6 (4)
C1—N1—H1	116 (2)	C12—C17—H17	120.2
C4—N1—H1	116.9 (19)	C16—C17—H17	120.2
C1—N2—C2	125.8 (2)	F2—C18—F3	107.8 (2)
C1—N2—H2A	108 (2)	F2—C18—F1	107.5 (2)
C2—N2—H2A	125 (2)	F3—C18—F1	106.8 (2)
O4—N3—O3	122.7 (3)	F2—C18—C4	112.7 (2)
O4—N3—C8	118.3 (3)	F3—C18—C4	110.3 (2)
O3—N3—C8	119.0 (3)	F1—C18—C4	111.5 (2)
C19—N4—C22	121.3 (2)	O6—C19—N5	120.7 (2)
C19—N4—H4	117 (2)	O6—C19—N4	121.2 (2)
C22—N4—H4	112 (2)	N5—C19—N4	118.0 (2)
C19—N5—C20	126.3 (2)	N5—C20—C23	110.1 (2)
C19—N5—H5	118 (3)	N5—C20—C21	108.9 (2)
C20—N5—H5	114 (3)	C23—C20—C21	109.0 (2)
O8—N6—O9	123.7 (3)	N5—C20—H20	109.6
O8—N6—C26	118.3 (3)	C23—C20—H20	109.6
O9—N6—C26	117.9 (3)	C21—C20—H20	109.6
C4—O5—H5A	112 (2)	C29—C21—C20	109.2 (2)
C22—O10—H10A	110 (3)	C29—C21—C22	113.3 (2)
O1—C1—N2	121.1 (2)	C20—C21—C22	109.2 (2)
O1—C1—N1	119.9 (2)	C29—C21—H21	108.3
N2—C1—N1	118.9 (2)	C20—C21—H21	108.3
N2—C2—C5	110.8 (2)	C22—C21—H21	108.3
N2—C2—C3	108.2 (2)	O10—C22—N4	113.2 (2)
C5—C2—C3	108.7 (2)	O10—C22—C21	109.0 (2)
N2—C2—H2	109.7	N4—C22—C21	107.7 (2)
C5—C2—H2	109.7	O10—C22—C36	110.0 (2)
C3—C2—H2	109.7	N4—C22—C36	107.4 (2)
C2—C3—C4	109.2 (2)	C21—C22—C36	109.5 (2)
C2—C3—C11	108.9 (2)	C28—C23—C24	120.1 (2)
C4—C3—C11	113.5 (2)	C28—C23—C20	120.1 (2)
C2—C3—H3	108.3	C24—C23—C20	119.6 (2)
C4—C3—H3	108.3	C25—C24—C23	120.4 (3)
C11—C3—H3	108.3	C25—C24—H24	119.8
O5—C4—N1	112.7 (2)	C23—C24—H24	119.8
O5—C4—C3	109.8 (2)	C24—C25—C26	118.3 (3)
N1—C4—C3	107.5 (2)	C24—C25—H25	120.8
O5—C4—C18	109.7 (2)	C26—C25—H25	120.8
N1—C4—C18	107.3 (2)	C27—C26—C25	123.1 (3)
C3—C4—C18	109.7 (2)	C27—C26—N6	118.8 (2)
C10—C5—C6	119.8 (2)	C25—C26—N6	118.1 (2)
C10—C5—C2	120.7 (2)	C26—C27—C28	117.9 (3)
C6—C5—C2	119.4 (2)	C26—C27—H27	121.1
C7—C6—C5	120.2 (3)	C28—C27—H27	121.1
C7—C6—H6	119.9	C23—C28—C27	120.1 (3)
C5—C6—H6	119.9	C23—C28—H28	120.0
C6—C7—C8	118.4 (3)	C27—C28—H28	120.0
C6—C7—H7	120.8	O7—C29—C30	121.0 (3)
C8—C7—H7	120.8	O7—C29—C21	119.2 (3)
C9—C8—C7	122.6 (2)	C30—C29—C21	119.9 (2)
C9—C8—N3	119.2 (2)	C31—C30—C35	119.2 (3)
C7—C8—N3	118.2 (3)	C31—C30—C29	123.4 (3)
C10—C9—C8	118.4 (3)	C35—C30—C29	117.5 (3)
C10—C9—H9	120.8	C32—C31—C30	120.0 (3)
C8—C9—H9	120.8	C32—C31—H31	120.0
C9—C10—C5	120.7 (3)	C30—C31—H31	120.0
C9—C10—H10	119.7	C33—C32—C31	120.3 (3)
C5—C10—H10	119.7	C33—C32—H32	119.9
O2—C11—C12	121.3 (2)	C31—C32—H32	119.9
O2—C11—C3	119.7 (3)	C34—C33—C32	120.0 (3)
C12—C11—C3	119.0 (2)	C34—C33—H33	120.0
C17—C12—C13	119.3 (3)	C32—C33—H33	120.0
C17—C12—C11	117.3 (3)	C33—C34—C35	120.4 (3)
C13—C12—C11	123.4 (2)	C33—C34—H34	119.8
C14—C13—C12	119.8 (3)	C35—C34—H34	119.8
C14—C13—H13	120.1	C34—C35—C30	120.1 (3)
C12—C13—H13	120.1	C34—C35—H35	119.9
C15—C14—C13	120.5 (4)	C30—C35—H35	120.0
C15—C14—H14	119.7	F4—C36—F6	108.0 (2)
C13—C14—H14	119.7	F4—C36—F5	107.5 (2)
C14—C15—C16	120.7 (4)	F6—C36—F5	107.1 (2)
C14—C15—H15	119.6	F4—C36—C22	112.1 (2)
C16—C15—H15	119.6	F6—C36—C22	110.6 (2)
C15—C16—C17	120.1 (3)	F5—C36—C22	111.3 (2)
C15—C16—H16	119.9	H11A—O11—H11B	105 (4)
C17—C16—H16	119.9	H12A—O12—H12B	102 (4)

C2—N2—C1—O1	175.8 (3)	C20—N5—C19—O6	178.1 (3)
C2—N2—C1—N1	−6.4 (4)	C20—N5—C19—N4	−3.9 (4)
C4—N1—C1—O1	−166.1 (2)	C22—N4—C19—O6	−165.8 (2)
C4—N1—C1—N2	16.1 (4)	C22—N4—C19—N5	16.1 (4)
C1—N2—C2—C5	144.1 (3)	C19—N5—C20—C23	141.1 (3)
C1—N2—C2—C3	25.0 (4)	C19—N5—C20—C21	21.7 (4)
N2—C2—C3—C4	−50.6 (3)	N5—C20—C21—C29	−172.7 (2)
C5—C2—C3—C4	−171.0 (2)	C23—C20—C21—C29	67.1 (3)
N2—C2—C3—C11	−175.1 (2)	N5—C20—C21—C22	−48.3 (3)
C5—C2—C3—C11	64.5 (3)	C23—C20—C21—C22	−168.5 (2)
C1—N1—C4—O5	78.2 (3)	C19—N4—C22—O10	76.4 (3)
C1—N1—C4—C3	−43.0 (3)	C19—N4—C22—C21	−44.1 (3)
C1—N1—C4—C18	−160.9 (2)	C19—N4—C22—C36	−162.0 (2)
C2—C3—C4—O5	−63.2 (2)	C29—C21—C22—O10	58.1 (3)
C11—C3—C4—O5	58.6 (3)	C20—C21—C22—O10	−63.9 (2)
C2—C3—C4—N1	59.8 (3)	C29—C21—C22—N4	−178.7 (2)
C11—C3—C4—N1	−178.4 (2)	C20—C21—C22—N4	59.3 (3)
C2—C3—C4—C18	176.1 (2)	C29—C21—C22—C36	−62.3 (3)
C11—C3—C4—C18	−62.1 (3)	C20—C21—C22—C36	175.7 (2)
N2—C2—C5—C10	136.7 (3)	N5—C20—C23—C28	135.7 (2)
C3—C2—C5—C10	−104.5 (3)	C21—C20—C23—C28	−104.9 (3)
N2—C2—C5—C6	−46.9 (3)	N5—C20—C23—C24	−47.9 (3)
C3—C2—C5—C6	71.9 (3)	C21—C20—C23—C24	71.5 (3)
C10—C5—C6—C7	1.0 (4)	C28—C23—C24—C25	0.5 (4)
C2—C5—C6—C7	−175.4 (3)	C20—C23—C24—C25	−175.8 (3)
C5—C6—C7—C8	−1.4 (4)	C23—C24—C25—C26	−2.2 (4)
C6—C7—C8—C9	0.5 (4)	C24—C25—C26—C27	1.8 (4)
C6—C7—C8—N3	−176.4 (3)	C24—C25—C26—N6	−176.5 (3)
O4—N3—C8—C9	−8.8 (4)	O8—N6—C26—C27	167.5 (3)
O3—N3—C8—C9	171.4 (3)	O9—N6—C26—C27	−15.0 (4)
O4—N3—C8—C7	168.2 (3)	O8—N6—C26—C25	−14.2 (4)
O3—N3—C8—C7	−11.5 (4)	O9—N6—C26—C25	163.4 (3)
C7—C8—C9—C10	0.9 (4)	C25—C26—C27—C28	0.3 (4)
N3—C8—C9—C10	177.8 (2)	N6—C26—C27—C28	178.5 (2)
C8—C9—C10—C5	−1.3 (4)	C24—C23—C28—C27	1.6 (4)
C6—C5—C10—C9	0.4 (4)	C20—C23—C28—C27	177.9 (2)
C2—C5—C10—C9	176.8 (2)	C26—C27—C28—C23	−2.0 (4)
C2—C3—C11—O2	58.5 (3)	C20—C21—C29—O7	55.1 (3)
C4—C3—C11—O2	−63.4 (3)	C22—C21—C29—O7	−66.9 (3)
C2—C3—C11—C12	−121.0 (3)	C20—C21—C29—C30	−124.5 (3)
C4—C3—C11—C12	117.1 (3)	C22—C21—C29—C30	113.6 (3)
O2—C11—C12—C17	14.1 (4)	O7—C29—C30—C31	−161.6 (3)
C3—C11—C12—C17	−166.4 (3)	C21—C29—C30—C31	17.9 (4)
O2—C11—C12—C13	−165.2 (3)	O7—C29—C30—C35	17.9 (4)
C3—C11—C12—C13	14.3 (4)	C21—C29—C30—C35	−162.6 (3)
C17—C12—C13—C14	−0.3 (5)	C35—C30—C31—C32	0.0 (5)
C11—C12—C13—C14	179.0 (3)	C29—C30—C31—C32	179.5 (3)
C12—C13—C14—C15	0.8 (6)	C30—C31—C32—C33	0.9 (5)
C13—C14—C15—C16	−0.1 (6)	C31—C32—C33—C34	−1.1 (6)
C14—C15—C16—C17	−1.0 (7)	C32—C33—C34—C35	0.5 (6)
C13—C12—C17—C16	−0.8 (5)	C33—C34—C35—C30	0.4 (6)
C11—C12—C17—C16	179.8 (3)	C31—C30—C35—C34	−0.6 (5)
C15—C16—C17—C12	1.5 (6)	C29—C30—C35—C34	179.9 (3)
O5—C4—C18—F2	71.4 (3)	O10—C22—C36—F4	72.3 (3)
N1—C4—C18—F2	−51.4 (3)	N4—C22—C36—F4	−51.3 (3)
C3—C4—C18—F2	−167.9 (2)	C21—C22—C36—F4	−167.9 (2)
O5—C4—C18—F3	−49.1 (3)	O10—C22—C36—F6	−48.3 (3)
N1—C4—C18—F3	−171.9 (2)	N4—C22—C36—F6	−171.9 (2)
C3—C4—C18—F3	71.6 (3)	C21—C22—C36—F6	71.5 (3)
O5—C4—C18—F1	−167.6 (2)	O10—C22—C36—F5	−167.2 (2)
N1—C4—C18—F1	69.7 (3)	N4—C22—C36—F5	69.2 (3)
C3—C4—C18—F1	−46.8 (3)	C21—C22—C36—F5	−47.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O11	0.92 (4)	2.11 (4)	2.903 (3)	144 (3)
N1—H1···O11ⁱ	0.95 (3)	2.08 (4)	3.011 (3)	167 (3)
N5—H5···O12ⁱⁱ	0.89 (4)	2.05 (4)	2.907 (3)	163 (3)
N4—H4···O12ⁱⁱⁱ	0.85 (4)	2.17 (4)	3.019 (3)	176 (3)
O5—H5A···O6^iv	0.89 (4)	1.78 (4)	2.678 (3)	178 (4)
O10—H10A···O1^v	0.85 (2)	1.82 (2)	2.672 (3)	178 (4)
O12—H12A···O5	0.85 (4)	2.13 (4)	2.817 (3)	137 (3)
O12—H12A···O2	0.85 (4)	2.32 (4)	3.026 (3)	140 (3)
O11—H11A···O10^vi	0.82 (4)	2.22 (4)	2.815 (3)	129 (3)
O11—H11A···O7^vi	0.82 (4)	2.27 (4)	3.009 (3)	150 (3)
O11—H11B···O6^vii	0.83 (4)	2.05 (4)	2.853 (3)	163 (4)
O12—H12B···O1^viii	0.82 (4)	2.12 (4)	2.840 (3)	147 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₄F₃N₃O₅·H₂O
M_r	427.34
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	113
a, b, c (Å)	14.389 (3), 9.0391 (18), 28.141 (6)
V (Å³)	3660.1 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.14
Crystal size (mm)	0.32 × 0.22 × 0.20

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (CrystalClear, Rigaku/MSC, 2002)
T_min, T_max	0.958, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	28524, 4437, 4222
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.107, 1.06
No. of reflections	4437
No. of parameters	575
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.31

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O11	0.92 (4)	2.11 (4)	2.903 (3)	144 (3)
N1—H1···O11ⁱ	0.95 (3)	2.08 (4)	3.011 (3)	167 (3)
N5—H5···O12ⁱⁱ	0.89 (4)	2.05 (4)	2.907 (3)	163 (3)
N4—H4···O12ⁱⁱⁱ	0.85 (4)	2.17 (4)	3.019 (3)	176 (3)
O5—H5A···O6^iv	0.89 (4)	1.78 (4)	2.678 (3)	178 (4)
O10—H10A···O1^v	0.85 (2)	1.82 (2)	2.672 (3)	178 (4)
O12—H12A···O5	0.85 (4)	2.13 (4)	2.817 (3)	137 (3)
O12—H12A···O2	0.85 (4)	2.32 (4)	3.026 (3)	140 (3)
O11—H11A···O10^vi	0.82 (4)	2.22 (4)	2.815 (3)	129 (3)
O11—H11A···O7^vi	0.82 (4)	2.27 (4)	3.009 (3)	150 (3)
O11—H11B···O6^vii	0.83 (4)	2.05 (4)	2.853 (3)	163 (4)
O12—H12B···O1^viii	0.82 (4)	2.12 (4)	2.840 (3)	147 (3)

Acknowledgements

The authors thank the Natural Science Foundation of Henan Province (grant No. 082300420110) and the Natural Science Foundation of Henan Province Education Department (grant No. 2007150036) for financial support.

References

Brier, S., Lemaire, D., DeBonis, S., Forest, E. & Kozielski, F. (2004). Biochemistry, 43, 13072–13082. Web of Science CrossRef PubMed CAS Google Scholar
Cochran, J. C., Gatial, J. E., Kapoor, T. M. & Gilbert, S. P. (2005). J. Biol. Chem. 280, 12658–12667. Web of Science CrossRef PubMed CAS Google Scholar
Hermann, B., Erwin, H. & Hansjorg, K. (2003). US patent No. 2 003 176 284. Google Scholar
Moran, M. M., Fanger, C., Chong, J. A., McNamara, C., Zhen, X. G. & Mandel-Brehm, J. (2007). WO Patent No. 2 007 073 505. Google Scholar
Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 65| Part 1| January 2009| Pages o87-o88

doi:10.1107/S160053680804124X

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

5-Benzoyl-4-hydr­­oxy-6-(4-nitro­phen­yl)-4-tri­fluoro­meth­yl-3,4,5,6-tetra­hydro­pyrimidin-2(1H)-one monohydrate

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Experimental

Crystal data

Data collection

Refinement

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Acknowledgements

References

organic compounds

5-Benzoyl-4-hydroxy-6-(4-nitrophenyl)-4-trifluoromethyl-3,4,5,6-tetrahydropyrimidin-2(1H)-one monohydrate