rac-6-Hy­droxy-4-(4-nitro­phen­yl)-5-(2-thienyl­carbon­yl)-6-(trifluoro­meth­yl)-3,4,5,6-tetra­hydro­pyrimidin-2(1H)-one monohydrate

Zhang, J.-L.; Wang, H.-S.; Niu, Y.-J.; Zhu, F.-X.

doi:10.1107/S1600536810041589

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Pages o2932-o2933

https://doi.org/10.1107/S1600536810041589

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rac-6-Hydroxy-4-(4-nitrophenyl)-5-(2-thienylcarbonyl)-6-(trifluoromethyl)-3,4,5,6-tetrahydropyrimidin-2(1H)-one monohydrate

Jian-Li Zhang,^a Hong-Sheng Wang,^a ^* Yu-Jiao Niu ^a and Feng-Xiang Zhu ^a

^aCollege of Chemistry and Chemical Engineering, Xuchang University, Xuchang, Henan Province, 461000, People's Republic of China
^*Correspondence e-mail: xcuwaller@163.com

(Received 29 September 2010; accepted 15 October 2010; online 23 October 2010)

The title compound, C₁₆H₁₂F₃N₃O₅S·H₂O, was prepared by reaction of 4-nitrobenzaldehyde, 4,4,4-trifluoro-1-(thiophen-2-yl)butane-1,3-dione and urea. The asymmetric unit contains two independent molecules, with essentially identical geometries and conformations. The dihydropyrimidine rings adopt a half-chair conformation. The dihedral angles between the benzene ring and the thiophene ring are 54.82 (8) and 58.72 (8)° in the two molecules. The molecular conformation of one of the molecules is stabilized by two intramolecular O—H⋯O hydrogen bonds, generating an S(6) ring. The crystal structure is stabilized by intermolecular O—H⋯O and N—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

C₁₆H₁₂F₃N₃O₅S·H₂O
M_r = 433.36
Orthorhombic, P n a 2₁
a = 14.1640 (13) Å
b = 9.136 (1) Å
c = 27.459 (3) Å
V = 3553.3 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 113 K
0.24 × 0.20 × 0.18 mm

Data collection

Rigaku Saturn724 CCD diffractometer
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2009 ) T_min = 0.941, T_max = 0.956
34133 measured reflections
7861 independent reflections
7466 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.091
S = 1.05
7861 reflections
563 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.27 e Å⁻³
Absolute structure: Flack (1983 ), 3539 Friedel pairs
Flack parameter: −0.01 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O12—H12A⋯O6	0.85 (3)	2.28 (3)	2.867 (2)	126 (2)
O12—H12A⋯O8	0.85 (3)	2.20 (3)	2.949 (2)	147 (3)
O12—H12B⋯O7ⁱ	0.79 (3)	2.11 (3)	2.852 (2)	156 (3)
N1—H1⋯O12ⁱⁱ	0.99 (2)	2.00 (2)	2.969 (2)	168.5 (19)
N2—H2⋯O12ⁱⁱⁱ	0.80 (3)	2.15 (3)	2.905 (2)	159 (2)
N5—H5⋯O11	0.82 (3)	2.15 (3)	2.903 (2)	153 (3)
N4—H4⋯O11^iv	0.84 (3)	2.17 (3)	2.991 (2)	166 (2)
O6—H6⋯O2^v	0.82 (3)	1.86 (3)	2.684 (2)	179 (3)
O1—H1A⋯O7^vi	0.93 (4)	1.76 (4)	2.684 (2)	175 (4)
O11—H11A⋯O2^vii	0.81 (3)	2.06 (3)	2.849 (2)	166 (3)
O11—H11B⋯O3^viii	0.83 (3)	2.23 (3)	2.968 (2)	148 (3)
O11—H11B⋯O1^viii	0.83 (3)	2.25 (3)	2.863 (2)	131 (3)
Symmetry codes: (i) x, y+1, z; (ii) $[-x+1, -y+1, z-{\script{1\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (v) $[-x+1, -y+1, z+{\script{1\over 2}}]$ ; (vi) $[-x+1, -y, z-{\script{1\over 2}}]$ ; (vii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (viii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrystalClear-SM Expert (Rigaku, 2009); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2009); software used to prepare material for publication: CrystalStructure.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810041589/fj2348sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810041589/fj2348Isup2.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). In addition, compounds that contain fluorine have special bioactivity, e.g. flumioxazin is a widely used herbicide (Hermann et al., 2003; Ulrich, 2004). This led us to focus our attention on the synthesis and bioactivity of these important fused perfluoroalkylated heterocyclic compounds. During the synthesis of DHPM derivatives, the title compound, an intermediate C₁₆H₁₄F₃N₃O₆S (I) was isolated and the structure confirmed by X-ray diffraction, in order to elucidate the reaction mechanism.

The title compound crystallizes with two independent molecules in the asymmetric unit. In the structure of the title molecule, the dihydropyrimidine ring adopts a half-chair conformation. The molecular conformation of one of the molecules is stabilized by two intramolecular O—H···O hydrogen bond, generating an S(6) ring. The crystal structure is stabilized by nine intermolecular hydrogen bonds (six O—H···O and three N—H···O) (Table 1). The dihedral angles between the pyridine ring and the thiophene ring are 54.82 (8)° and 58.72 (8)° in the two molecules.

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 refluxing for 3 h a stirred solution of 4-nitrobenzaldehyde (0.30 g, 2 mmol), 4,4,4-trifluoro-1- (thiophen-2-yl)butane-1,3-dione (0.51 g, 2.3 mmol) and urea (0.18 g, 3 mmol) in 3 ml of anhydrous ethanol, the reaction catalyzed by sulfamic acid (0.06 g). The solvent was evaporated in vacuo and the residue was washed with water. The title compound was recrystallized from 50% aqueous ethanol and single crystals of (I) were obtained by slow evaporation.

Structure description 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).

Computing details top

Data collection: CrystalClear-SM Expert (Rigaku, 2009); cell refinement: CrystalClear-SM Expert (Rigaku, 2009); data reduction: CrystalClear-SM Expert (Rigaku, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2009); software used to prepare material for publication: CrystalStructure (Rigaku, 2009).

Figures top

	Fig. 1. Molecular configuration and atom numbering scheme for (I), with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The packing diagram of the title compound. Intermolecular hydrogen bonds are shown as dashed line.

rac-6-Hydroxy-4-(4-nitrophenyl)-5-(2-thienylcarbonyl)-6- (trifluoromethyl)-3,4,5,6-tetrahydropyrimidin-2(1H)-one monohydrate top

Crystal data top

C₁₆H₁₂F₃N₃O₅S·H₂O	F(000) = 1776
M_r = 433.36	D_x = 1.620 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2c -2n	Cell parameters from 9674 reflections
a = 14.1640 (13) Å	θ = 1.6–27.9°
b = 9.136 (1) Å	µ = 0.26 mm⁻¹
c = 27.459 (3) Å	T = 113 K
V = 3553.3 (6) Å³	Prism, colorless
Z = 8	0.24 × 0.20 × 0.18 mm

Data collection top

Rigaku Saturn724 CCD diffractometer	7861 independent reflections
Radiation source: rotating anode	7466 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.031
Detector resolution: 14.222 pixels mm^-1	θ_max = 27.9°, θ_min = 1.5°
ω scans	h = −18→18
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2009)	k = −12→11
T_min = 0.941, T_max = 0.956	l = −35→36
34133 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.091	w = 1/[σ²(F_o²) + (0.0567P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
7861 reflections	Δρ_max = 0.37 e Å⁻³
563 parameters	Δρ_min = −0.27 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 3539 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (5)

Crystal data top

C₁₆H₁₂F₃N₃O₅S·H₂O	V = 3553.3 (6) Å³
M_r = 433.36	Z = 8
Orthorhombic, Pna2₁	Mo Kα radiation
a = 14.1640 (13) Å	µ = 0.26 mm⁻¹
b = 9.136 (1) Å	T = 113 K
c = 27.459 (3) Å	0.24 × 0.20 × 0.18 mm

Data collection top

Rigaku Saturn724 CCD diffractometer	7861 independent reflections
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2009)	7466 reflections with I > 2σ(I)
T_min = 0.941, T_max = 0.956	R_int = 0.031
34133 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.091	Δρ_max = 0.37 e Å⁻³
S = 1.05	Δρ_min = −0.27 e Å⁻³
7861 reflections	Absolute structure: Flack (1983), 3539 Friedel pairs
563 parameters	Absolute structure parameter: −0.01 (5)
1 restraint

Special details top

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

Refinement. Refinement of 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 > σ(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
S1	0.60772 (5)	−0.35697 (6)	0.08791 (3)	0.03689 (15)
F1	0.37968 (10)	−0.23469 (13)	0.00751 (6)	0.0331 (3)
F2	0.27429 (8)	−0.07998 (14)	−0.01598 (5)	0.0274 (3)
F3	0.35284 (9)	−0.04033 (14)	0.04972 (5)	0.0292 (3)
O1	0.45567 (10)	−0.08713 (15)	−0.06818 (5)	0.0212 (3)
O2	0.43350 (10)	0.36232 (14)	−0.06593 (5)	0.0211 (3)
O3	0.59480 (11)	−0.23377 (16)	−0.01125 (6)	0.0282 (3)
O4	0.89623 (12)	0.33821 (17)	0.13355 (6)	0.0335 (4)
O5	0.96906 (14)	0.1399 (2)	0.11251 (7)	0.0467 (5)
N1	0.40188 (13)	0.13684 (17)	−0.03407 (6)	0.0180 (3)
N2	0.55597 (13)	0.2246 (2)	−0.04098 (7)	0.0203 (4)
N3	0.90201 (14)	0.22519 (19)	0.10965 (7)	0.0249 (4)
C1	0.43619 (13)	−0.01001 (19)	−0.02507 (7)	0.0165 (4)
C2	0.46358 (14)	0.2445 (2)	−0.04839 (7)	0.0183 (4)
C3	0.60082 (14)	0.0912 (2)	−0.02294 (7)	0.0173 (4)
H3	0.6249	0.0323	−0.0510	0.021*
C4	0.52713 (14)	0.00176 (19)	0.00539 (7)	0.0172 (4)
H4A	0.5117	0.0564	0.0359	0.021*
C5	0.68228 (15)	0.1286 (2)	0.01111 (7)	0.0182 (4)
C6	0.67296 (15)	0.2434 (2)	0.04432 (8)	0.0216 (4)
H6A	0.6169	0.3005	0.0445	0.026*
C7	0.74425 (16)	0.2748 (2)	0.07696 (7)	0.0214 (4)
H7	0.7383	0.3535	0.0994	0.026*
C8	0.82467 (15)	0.1886 (2)	0.07617 (7)	0.0205 (4)
C9	0.83640 (15)	0.0731 (2)	0.04422 (8)	0.0226 (4)
H9	0.8922	0.0154	0.0447	0.027*
C10	0.76357 (14)	0.0438 (2)	0.01115 (7)	0.0202 (4)
H10	0.7698	−0.0346	−0.0114	0.024*
C11	0.35973 (15)	−0.0915 (2)	0.00413 (7)	0.0203 (4)
C12	0.56951 (15)	−0.1468 (2)	0.01993 (8)	0.0206 (4)
C13	0.57782 (15)	−0.1808 (2)	0.07158 (8)	0.0217 (4)
C14	0.56852 (15)	−0.0877 (2)	0.11324 (7)	0.0241 (4)
H14	0.5543	0.0139	0.1124	0.029*
C15	0.58417 (19)	−0.1726 (3)	0.15664 (9)	0.0361 (6)
H15	0.5803	−0.1326	0.1885	0.043*
C16	0.60494 (19)	−0.3148 (3)	0.14778 (10)	0.0407 (7)
H16	0.6168	−0.3842	0.1728	0.049*
S2	0.87505 (5)	0.87073 (6)	0.23286 (2)	0.03609 (15)
F4	0.62278 (9)	0.54205 (14)	0.26486 (4)	0.0278 (3)
F5	0.64890 (10)	0.73570 (13)	0.30749 (6)	0.0319 (3)
F6	0.54339 (9)	0.57986 (14)	0.33042 (5)	0.0261 (3)
O6	0.72494 (11)	0.58706 (15)	0.38319 (5)	0.0206 (3)
O7	0.70213 (11)	0.13746 (14)	0.38037 (5)	0.0213 (3)
O8	0.86907 (11)	0.72990 (16)	0.32953 (6)	0.0253 (3)
O9	1.16517 (13)	0.15713 (17)	0.18214 (6)	0.0363 (4)
O10	1.23927 (14)	0.3536 (2)	0.20196 (8)	0.0558 (6)
N4	0.67149 (13)	0.36304 (16)	0.34850 (6)	0.0174 (3)
N5	0.82537 (13)	0.27411 (19)	0.35508 (7)	0.0201 (4)
N6	1.17126 (14)	0.2717 (2)	0.20498 (7)	0.0264 (4)
C17	0.70562 (14)	0.5113 (2)	0.34018 (7)	0.0181 (4)
C18	0.73277 (14)	0.2537 (2)	0.36261 (7)	0.0172 (4)
C19	0.87044 (14)	0.4083 (2)	0.33745 (7)	0.0194 (4)
H19	0.8951	0.4658	0.3657	0.023*
C20	0.79665 (14)	0.49985 (19)	0.30975 (7)	0.0173 (4)
H20	0.7814	0.4485	0.2786	0.021*
C21	0.62941 (15)	0.5919 (2)	0.31056 (8)	0.0208 (4)
C22	0.95101 (14)	0.37086 (19)	0.30321 (7)	0.0173 (4)
C23	0.94011 (15)	0.2601 (2)	0.26815 (8)	0.0222 (4)
H23	0.8829	0.2060	0.2669	0.027*
C24	1.01085 (15)	0.2290 (2)	0.23565 (7)	0.0218 (4)
H24	1.0034	0.1537	0.2121	0.026*
C25	1.09372 (15)	0.3103 (2)	0.23800 (7)	0.0205 (4)
C26	1.10671 (16)	0.4235 (2)	0.27159 (8)	0.0236 (4)
H26	1.1635	0.4789	0.2720	0.028*
C27	1.03457 (14)	0.4527 (2)	0.30426 (8)	0.0211 (4)
H27	1.0419	0.5287	0.3275	0.025*
C28	0.83971 (14)	0.6501 (2)	0.29737 (7)	0.0190 (4)
C29	0.84472 (15)	0.6933 (2)	0.24656 (8)	0.0210 (4)
C30	0.82926 (16)	0.6111 (2)	0.20372 (8)	0.0251 (4)
H30	0.8130	0.5102	0.2032	0.030*
C31	0.84114 (19)	0.6988 (3)	0.16187 (9)	0.0356 (6)
H31	0.8340	0.6624	0.1297	0.043*
C32	0.8636 (2)	0.8396 (3)	0.17194 (10)	0.0391 (6)
H32	0.8720	0.9128	0.1478	0.047*
O11	0.98547 (11)	0.12871 (16)	0.40001 (6)	0.0222 (3)
O12	0.78322 (11)	0.87168 (16)	0.41523 (6)	0.0219 (3)
H12A	0.785 (2)	0.818 (3)	0.3900 (11)	0.043 (8)*
H12B	0.777 (2)	0.950 (4)	0.4040 (12)	0.058 (10)*
H1	0.3382 (17)	0.146 (2)	−0.0483 (9)	0.020 (6)*
H2	0.5907 (17)	0.283 (3)	−0.0528 (9)	0.022 (6)*
H5	0.859 (2)	0.209 (3)	0.3656 (10)	0.035 (7)*
H4	0.615 (2)	0.362 (3)	0.3582 (9)	0.028 (7)*
H6	0.6766 (19)	0.603 (3)	0.3989 (10)	0.029 (7)*
H1A	0.399 (3)	−0.106 (4)	−0.0845 (14)	0.073 (11)*
H11A	0.9996 (19)	0.051 (3)	0.4119 (10)	0.034 (8)*
H11B	0.982 (2)	0.188 (3)	0.4227 (11)	0.042 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0438 (4)	0.0252 (3)	0.0416 (4)	0.0070 (2)	−0.0030 (3)	0.0096 (2)
F1	0.0316 (8)	0.0147 (6)	0.0531 (9)	−0.0018 (5)	0.0029 (7)	0.0088 (6)
F2	0.0176 (6)	0.0335 (7)	0.0311 (7)	−0.0052 (5)	−0.0027 (5)	0.0088 (5)
F3	0.0302 (7)	0.0358 (7)	0.0216 (6)	−0.0038 (5)	0.0023 (6)	0.0011 (5)
O1	0.0194 (8)	0.0232 (7)	0.0210 (7)	0.0013 (6)	−0.0034 (6)	−0.0063 (6)
O2	0.0199 (8)	0.0173 (6)	0.0261 (7)	−0.0003 (5)	−0.0042 (6)	0.0053 (5)
O3	0.0308 (9)	0.0224 (7)	0.0313 (8)	0.0083 (6)	−0.0068 (7)	−0.0071 (6)
O4	0.0384 (10)	0.0298 (8)	0.0322 (9)	−0.0065 (7)	−0.0105 (8)	−0.0042 (7)
O5	0.0321 (11)	0.0551 (11)	0.0528 (12)	0.0129 (8)	−0.0214 (9)	−0.0176 (10)
N1	0.0175 (9)	0.0135 (8)	0.0230 (8)	0.0008 (6)	−0.0030 (7)	0.0024 (6)
N2	0.0158 (9)	0.0194 (8)	0.0256 (9)	−0.0023 (7)	−0.0031 (7)	0.0076 (7)
N3	0.0253 (10)	0.0276 (9)	0.0219 (9)	−0.0060 (7)	−0.0058 (8)	0.0032 (7)
C1	0.0171 (10)	0.0132 (8)	0.0192 (9)	−0.0001 (7)	−0.0034 (8)	−0.0014 (7)
C2	0.0183 (10)	0.0200 (9)	0.0167 (9)	−0.0010 (8)	0.0011 (8)	0.0017 (7)
C3	0.0160 (10)	0.0163 (8)	0.0196 (9)	0.0014 (7)	−0.0007 (8)	0.0005 (7)
C4	0.0180 (10)	0.0138 (8)	0.0199 (9)	0.0017 (7)	−0.0020 (8)	−0.0001 (7)
C5	0.0181 (10)	0.0180 (9)	0.0185 (9)	−0.0018 (7)	−0.0011 (8)	0.0031 (7)
C6	0.0189 (11)	0.0213 (9)	0.0246 (10)	0.0016 (8)	−0.0020 (8)	−0.0015 (8)
C7	0.0236 (11)	0.0203 (9)	0.0204 (10)	−0.0017 (8)	−0.0001 (8)	−0.0035 (8)
C8	0.0198 (11)	0.0237 (9)	0.0180 (9)	−0.0054 (8)	−0.0038 (8)	0.0039 (7)
C9	0.0201 (11)	0.0214 (9)	0.0265 (10)	0.0001 (8)	−0.0010 (8)	−0.0006 (8)
C10	0.0199 (11)	0.0184 (9)	0.0222 (10)	0.0010 (8)	−0.0027 (8)	−0.0009 (8)
C11	0.0209 (11)	0.0185 (9)	0.0216 (10)	0.0010 (7)	−0.0022 (8)	0.0017 (7)
C12	0.0154 (10)	0.0169 (9)	0.0296 (11)	−0.0006 (7)	−0.0048 (9)	0.0002 (8)
C13	0.0184 (11)	0.0163 (9)	0.0303 (10)	−0.0008 (8)	−0.0060 (9)	0.0055 (7)
C14	0.0208 (11)	0.0311 (10)	0.0205 (10)	0.0064 (8)	−0.0012 (8)	0.0112 (8)
C15	0.0361 (15)	0.0453 (14)	0.0269 (12)	0.0058 (11)	−0.0007 (11)	0.0050 (10)
C16	0.0357 (15)	0.0459 (16)	0.0405 (15)	0.0049 (12)	−0.0027 (12)	0.0243 (12)
S2	0.0525 (4)	0.0218 (2)	0.0340 (3)	−0.0066 (2)	0.0044 (3)	0.0062 (2)
F4	0.0294 (7)	0.0327 (7)	0.0213 (6)	0.0030 (5)	−0.0034 (5)	0.0000 (5)
F5	0.0323 (7)	0.0156 (5)	0.0478 (8)	0.0023 (5)	−0.0039 (7)	0.0052 (6)
F6	0.0173 (6)	0.0315 (6)	0.0296 (6)	0.0051 (5)	0.0031 (5)	0.0058 (5)
O6	0.0196 (8)	0.0229 (7)	0.0193 (7)	−0.0004 (6)	0.0025 (6)	−0.0042 (6)
O7	0.0226 (8)	0.0160 (7)	0.0253 (7)	0.0012 (5)	0.0047 (6)	0.0047 (5)
O8	0.0287 (9)	0.0236 (7)	0.0236 (7)	−0.0073 (6)	0.0028 (6)	−0.0041 (6)
O9	0.0433 (11)	0.0295 (8)	0.0361 (9)	0.0045 (7)	0.0192 (8)	−0.0046 (7)
O10	0.0339 (11)	0.0690 (14)	0.0646 (14)	−0.0199 (10)	0.0273 (10)	−0.0271 (11)
N4	0.0145 (9)	0.0147 (7)	0.0231 (9)	0.0011 (6)	0.0033 (7)	0.0030 (6)
N5	0.0184 (9)	0.0171 (8)	0.0247 (9)	0.0038 (7)	0.0033 (7)	0.0054 (7)
N6	0.0239 (10)	0.0317 (9)	0.0238 (9)	0.0025 (8)	0.0045 (8)	0.0008 (8)
C17	0.0184 (11)	0.0150 (8)	0.0210 (10)	−0.0004 (7)	0.0017 (8)	−0.0002 (7)
C18	0.0185 (10)	0.0163 (8)	0.0167 (9)	0.0006 (8)	0.0032 (8)	0.0000 (7)
C19	0.0202 (11)	0.0184 (9)	0.0196 (9)	0.0012 (8)	0.0037 (8)	0.0016 (7)
C20	0.0181 (10)	0.0153 (8)	0.0185 (9)	0.0002 (7)	0.0015 (8)	−0.0015 (7)
C21	0.0232 (11)	0.0168 (9)	0.0225 (10)	0.0002 (7)	0.0017 (8)	0.0005 (7)
C22	0.0179 (10)	0.0165 (9)	0.0174 (9)	0.0027 (7)	0.0032 (8)	0.0014 (7)
C23	0.0201 (11)	0.0199 (9)	0.0266 (11)	−0.0033 (8)	0.0001 (9)	−0.0031 (8)
C24	0.0222 (11)	0.0210 (9)	0.0222 (10)	0.0015 (8)	−0.0004 (9)	−0.0023 (8)
C25	0.0198 (11)	0.0215 (9)	0.0203 (9)	0.0048 (8)	0.0043 (8)	0.0029 (8)
C26	0.0185 (11)	0.0259 (10)	0.0264 (11)	−0.0031 (8)	0.0033 (9)	0.0021 (8)
C27	0.0220 (11)	0.0198 (9)	0.0215 (9)	−0.0002 (8)	−0.0009 (9)	−0.0017 (8)
C28	0.0177 (10)	0.0167 (9)	0.0226 (10)	0.0001 (7)	0.0031 (8)	0.0005 (7)
C29	0.0180 (11)	0.0192 (9)	0.0258 (10)	−0.0012 (8)	0.0022 (8)	0.0009 (8)
C30	0.0264 (12)	0.0282 (10)	0.0208 (10)	−0.0069 (8)	0.0033 (9)	−0.0006 (8)
C31	0.0333 (15)	0.0496 (15)	0.0238 (11)	−0.0044 (11)	0.0023 (10)	0.0034 (10)
C32	0.0449 (16)	0.0382 (13)	0.0342 (13)	−0.0031 (11)	0.0040 (12)	0.0150 (11)
O11	0.0262 (9)	0.0159 (7)	0.0245 (8)	0.0022 (6)	0.0001 (6)	−0.0019 (6)
O12	0.0239 (8)	0.0178 (7)	0.0242 (8)	0.0026 (6)	0.0004 (6)	−0.0026 (6)

Geometric parameters (Å, º) top

S1—C16	1.689 (3)	F4—C21	1.338 (2)
S1—C13	1.724 (2)	F5—C21	1.345 (2)
F1—C11	1.341 (2)	F6—C21	1.339 (2)
F2—C11	1.334 (2)	O6—C17	1.396 (2)
F3—C11	1.340 (2)	O6—H6	0.82 (3)
O1—C1	1.405 (2)	O7—C18	1.247 (2)
O1—H1A	0.93 (4)	O8—C28	1.218 (2)
O2—C2	1.254 (2)	O9—N6	1.224 (2)
O3—C12	1.222 (3)	O10—N6	1.222 (3)
O4—N3	1.226 (2)	N4—C18	1.379 (2)
O5—N3	1.231 (3)	N4—C17	1.456 (2)
N1—C2	1.373 (2)	N4—H4	0.84 (3)
N1—C1	1.448 (2)	N5—C18	1.341 (3)
N1—H1	0.99 (2)	N5—C19	1.465 (2)
N2—C2	1.337 (3)	N5—H5	0.82 (3)
N2—C3	1.462 (2)	N6—C25	1.467 (3)
N2—H2	0.80 (3)	C17—C21	1.539 (3)
N3—C8	1.469 (3)	C17—C20	1.540 (3)
C1—C4	1.540 (3)	C19—C22	1.518 (3)
C1—C11	1.540 (3)	C19—C20	1.539 (3)
C3—C5	1.524 (3)	C19—H19	1.0000
C3—C4	1.537 (3)	C20—C28	1.540 (3)
C3—H3	1.0000	C20—H20	1.0000
C4—C12	1.537 (3)	C22—C27	1.400 (3)
C4—H4A	1.0000	C22—C23	1.405 (3)
C5—C10	1.388 (3)	C23—C24	1.372 (3)
C5—C6	1.396 (3)	C23—H23	0.9500
C6—C7	1.380 (3)	C24—C25	1.391 (3)
C6—H6A	0.9500	C24—H24	0.9500
C7—C8	1.385 (3)	C25—C26	1.398 (3)
C7—H7	0.9500	C26—C27	1.386 (3)
C8—C9	1.382 (3)	C26—H26	0.9500
C9—C10	1.400 (3)	C27—H27	0.9500
C9—H9	0.9500	C28—C29	1.452 (3)
C10—H10	0.9500	C29—C30	1.413 (3)
C12—C13	1.457 (3)	C30—C31	1.411 (3)
C13—C14	1.432 (3)	C30—H30	0.9500
C14—C15	1.439 (3)	C31—C32	1.354 (4)
C14—H14	0.9500	C31—H31	0.9500
C15—C16	1.355 (4)	C32—H32	0.9500
C15—H15	0.9500	O11—H11A	0.81 (3)
C16—H16	0.9500	O11—H11B	0.83 (3)
S2—C32	1.705 (3)	O12—H12A	0.85 (3)
S2—C29	1.719 (2)	O12—H12B	0.79 (3)

C16—S1—C13	91.98 (12)	C17—O6—H6	111.8 (18)
C1—O1—H1A	109 (2)	C18—N4—C17	120.59 (17)
C2—N1—C1	119.93 (17)	C18—N4—H4	120.1 (17)
C2—N1—H1	114.3 (13)	C17—N4—H4	111.9 (16)
C1—N1—H1	116.7 (13)	C18—N5—C19	126.40 (17)
C2—N2—C3	126.19 (17)	C18—N5—H5	115 (2)
C2—N2—H2	116.9 (18)	C19—N5—H5	118 (2)
C3—N2—H2	115.4 (18)	O10—N6—O9	122.99 (19)
O4—N3—O5	123.40 (19)	O10—N6—C25	118.99 (18)
O4—N3—C8	118.49 (19)	O9—N6—C25	118.01 (18)
O5—N3—C8	118.10 (18)	O6—C17—N4	113.17 (16)
O1—C1—N1	112.75 (16)	O6—C17—C21	110.32 (15)
O1—C1—C4	109.18 (15)	N4—C17—C21	107.17 (16)
N1—C1—C4	107.98 (14)	O6—C17—C20	109.18 (16)
O1—C1—C11	109.54 (15)	N4—C17—C20	107.44 (15)
N1—C1—C11	107.52 (16)	C21—C17—C20	109.46 (16)
C4—C1—C11	109.84 (16)	O7—C18—N5	121.27 (18)
O2—C2—N2	120.51 (18)	O7—C18—N4	120.53 (18)
O2—C2—N1	120.57 (18)	N5—C18—N4	118.16 (17)
N2—C2—N1	118.82 (18)	N5—C19—C22	110.10 (16)
N2—C3—C5	110.45 (16)	N5—C19—C20	108.79 (16)
N2—C3—C4	108.65 (16)	C22—C19—C20	109.09 (16)
C5—C3—C4	108.86 (16)	N5—C19—H19	109.6
N2—C3—H3	109.6	C22—C19—H19	109.6
C5—C3—H3	109.6	C20—C19—H19	109.6
C4—C3—H3	109.6	C19—C20—C28	108.92 (16)
C3—C4—C12	109.60 (16)	C19—C20—C17	109.72 (15)
C3—C4—C1	109.30 (15)	C28—C20—C17	113.00 (15)
C12—C4—C1	113.97 (15)	C19—C20—H20	108.4
C3—C4—H4A	107.9	C28—C20—H20	108.4
C12—C4—H4A	107.9	C17—C20—H20	108.4
C1—C4—H4A	107.9	F4—C21—F6	106.85 (17)
C10—C5—C6	119.84 (19)	F4—C21—F5	106.75 (16)
C10—C5—C3	120.19 (17)	F6—C21—F5	107.02 (16)
C6—C5—C3	119.87 (18)	F4—C21—C17	112.44 (16)
C7—C6—C5	120.74 (19)	F6—C21—C17	112.55 (16)
C7—C6—H6A	119.6	F5—C21—C17	110.88 (16)
C5—C6—H6A	119.6	C27—C22—C23	119.43 (18)
C6—C7—C8	118.24 (18)	C27—C22—C19	120.17 (17)
C6—C7—H7	120.9	C23—C22—C19	120.28 (18)
C8—C7—H7	120.9	C24—C23—C22	120.99 (19)
C9—C8—C7	122.89 (19)	C24—C23—H23	119.5
C9—C8—N3	118.78 (19)	C22—C23—H23	119.5
C7—C8—N3	118.29 (18)	C23—C24—C25	118.40 (19)
C8—C9—C10	117.99 (19)	C23—C24—H24	120.8
C8—C9—H9	121.0	C25—C24—H24	120.8
C10—C9—H9	121.0	C24—C25—C26	122.47 (19)
C5—C10—C9	120.30 (18)	C24—C25—N6	118.35 (18)
C5—C10—H10	119.9	C26—C25—N6	119.15 (19)
C9—C10—H10	119.9	C27—C26—C25	118.2 (2)
F2—C11—F3	107.04 (16)	C27—C26—H26	120.9
F2—C11—F1	107.27 (16)	C25—C26—H26	120.9
F3—C11—F1	106.93 (16)	C26—C27—C22	120.49 (19)
F2—C11—C1	112.58 (16)	C26—C27—H27	119.8
F3—C11—C1	111.65 (16)	C22—C27—H27	119.8
F1—C11—C1	111.06 (16)	O8—C28—C29	121.14 (18)
O3—C12—C13	121.33 (19)	O8—C28—C20	120.58 (18)
O3—C12—C4	120.45 (19)	C29—C28—C20	118.28 (17)
C13—C12—C4	118.22 (18)	C30—C29—C28	130.41 (18)
C14—C13—C12	130.08 (18)	C30—C29—S2	110.97 (16)
C14—C13—S1	111.70 (15)	C28—C29—S2	118.61 (15)
C12—C13—S1	118.18 (16)	C31—C30—C29	110.97 (19)
C13—C14—C15	109.10 (19)	C31—C30—H30	124.5
C13—C14—H14	125.4	C29—C30—H30	124.5
C15—C14—H14	125.4	C32—C31—C30	113.7 (2)
C16—C15—C14	113.7 (2)	C32—C31—H31	123.2
C16—C15—H15	123.2	C30—C31—H31	123.2
C14—C15—H15	123.2	C31—C32—S2	112.42 (19)
C15—C16—S1	113.50 (19)	C31—C32—H32	123.8
C15—C16—H16	123.3	S2—C32—H32	123.8
S1—C16—H16	123.3	H11A—O11—H11B	107 (3)
C32—S2—C29	91.93 (12)	H12A—O12—H12B	102 (3)

C2—N1—C1—O1	−75.5 (2)	C18—N4—C17—O6	−75.2 (2)
C2—N1—C1—C4	45.2 (2)	C18—N4—C17—C21	162.97 (17)
C2—N1—C1—C11	163.65 (17)	C18—N4—C17—C20	45.4 (2)
C3—N2—C2—O2	−177.07 (18)	C19—N5—C18—O7	−175.88 (19)
C3—N2—C2—N1	6.4 (3)	C19—N5—C18—N4	6.5 (3)
C1—N1—C2—O2	165.12 (18)	C17—N4—C18—O7	163.48 (18)
C1—N1—C2—N2	−18.3 (3)	C17—N4—C18—N5	−18.9 (3)
C2—N2—C3—C5	−142.2 (2)	C18—N5—C19—C22	−142.0 (2)
C2—N2—C3—C4	−22.9 (3)	C18—N5—C19—C20	−22.5 (3)
N2—C3—C4—C12	173.84 (16)	N5—C19—C20—C28	172.20 (16)
C5—C3—C4—C12	−65.8 (2)	C22—C19—C20—C28	−67.68 (19)
N2—C3—C4—C1	48.3 (2)	N5—C19—C20—C17	48.0 (2)
C5—C3—C4—C1	168.61 (15)	C22—C19—C20—C17	168.15 (15)
O1—C1—C4—C3	63.20 (18)	O6—C17—C20—C19	63.79 (19)
N1—C1—C4—C3	−59.71 (19)	N4—C17—C20—C19	−59.30 (19)
C11—C1—C4—C3	−176.67 (15)	C21—C17—C20—C19	−175.35 (15)
O1—C1—C4—C12	−59.8 (2)	O6—C17—C20—C28	−58.0 (2)
N1—C1—C4—C12	177.29 (17)	N4—C17—C20—C28	178.94 (16)
C11—C1—C4—C12	60.3 (2)	C21—C17—C20—C28	62.9 (2)
N2—C3—C5—C10	−143.50 (19)	O6—C17—C21—F4	166.64 (15)
C4—C3—C5—C10	97.3 (2)	N4—C17—C21—F4	−69.8 (2)
N2—C3—C5—C6	40.2 (2)	C20—C17—C21—F4	46.5 (2)
C4—C3—C5—C6	−79.0 (2)	O6—C17—C21—F6	−72.6 (2)
C10—C5—C6—C7	0.8 (3)	N4—C17—C21—F6	51.0 (2)
C3—C5—C6—C7	177.05 (18)	C20—C17—C21—F6	167.20 (15)
C5—C6—C7—C8	−0.6 (3)	O6—C17—C21—F5	47.2 (2)
C6—C7—C8—C9	0.0 (3)	N4—C17—C21—F5	170.82 (16)
C6—C7—C8—N3	177.81 (18)	C20—C17—C21—F5	−73.0 (2)
O4—N3—C8—C9	170.99 (19)	N5—C19—C22—C27	−141.55 (19)
O5—N3—C8—C9	−9.6 (3)	C20—C19—C22—C27	99.1 (2)
O4—N3—C8—C7	−6.9 (3)	N5—C19—C22—C23	42.6 (2)
O5—N3—C8—C7	172.6 (2)	C20—C19—C22—C23	−76.8 (2)
C7—C8—C9—C10	0.4 (3)	C27—C22—C23—C24	1.4 (3)
N3—C8—C9—C10	−177.31 (18)	C19—C22—C23—C24	177.32 (18)
C6—C5—C10—C9	−0.2 (3)	C22—C23—C24—C25	−0.4 (3)
C3—C5—C10—C9	−176.53 (18)	C23—C24—C25—C26	−1.1 (3)
C8—C9—C10—C5	−0.3 (3)	C23—C24—C25—N6	176.76 (18)
O1—C1—C11—F2	−72.7 (2)	O10—N6—C25—C24	170.3 (2)
N1—C1—C11—F2	50.2 (2)	O9—N6—C25—C24	−10.7 (3)
C4—C1—C11—F2	167.44 (15)	O10—N6—C25—C26	−11.8 (3)
O1—C1—C11—F3	166.91 (15)	O9—N6—C25—C26	167.2 (2)
N1—C1—C11—F3	−70.3 (2)	C24—C25—C26—C27	1.4 (3)
C4—C1—C11—F3	47.0 (2)	N6—C25—C26—C27	−176.41 (19)
O1—C1—C11—F1	47.7 (2)	C25—C26—C27—C22	−0.3 (3)
N1—C1—C11—F1	170.49 (16)	C23—C22—C27—C26	−1.1 (3)
C4—C1—C11—F1	−72.3 (2)	C19—C22—C27—C26	−176.98 (19)
C3—C4—C12—O3	−62.2 (2)	C19—C20—C28—O8	−58.2 (2)
C1—C4—C12—O3	60.6 (3)	C17—C20—C28—O8	64.0 (2)
C3—C4—C12—C13	118.2 (2)	C19—C20—C28—C29	121.5 (2)
C1—C4—C12—C13	−118.9 (2)	C17—C20—C28—C29	−116.3 (2)
O3—C12—C13—C14	167.7 (2)	O8—C28—C29—C30	168.8 (2)
C4—C12—C13—C14	−12.8 (3)	C20—C28—C29—C30	−10.9 (3)
O3—C12—C13—S1	−9.5 (3)	O8—C28—C29—S2	−10.4 (3)
C4—C12—C13—S1	170.01 (15)	C20—C28—C29—S2	169.89 (14)
C16—S1—C13—C14	1.81 (19)	C32—S2—C29—C30	1.98 (19)
C16—S1—C13—C12	179.52 (18)	C32—S2—C29—C28	−178.64 (19)
C12—C13—C14—C15	−179.3 (2)	C28—C29—C30—C31	179.5 (2)
S1—C13—C14—C15	−1.9 (2)	S2—C29—C30—C31	−1.3 (2)
C13—C14—C15—C16	1.1 (3)	C29—C30—C31—C32	−0.4 (3)
C14—C15—C16—S1	0.2 (3)	C30—C31—C32—S2	1.9 (3)
C13—S1—C16—C15	−1.2 (2)	C29—S2—C32—C31	−2.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O12—H12A···O6	0.85 (3)	2.28 (3)	2.867 (2)	126 (2)
O12—H12A···O8	0.85 (3)	2.20 (3)	2.949 (2)	147 (3)
O12—H12B···O7ⁱ	0.79 (3)	2.11 (3)	2.852 (2)	156 (3)
N1—H1···O12ⁱⁱ	0.99 (2)	2.00 (2)	2.969 (2)	168.5 (19)
N2—H2···O12ⁱⁱⁱ	0.80 (3)	2.15 (3)	2.905 (2)	159 (2)
N5—H5···O11	0.82 (3)	2.15 (3)	2.903 (2)	153 (3)
N4—H4···O11^iv	0.84 (3)	2.17 (3)	2.991 (2)	166 (2)
O6—H6···O2^v	0.82 (3)	1.86 (3)	2.684 (2)	179 (3)
O1—H1A···O7^vi	0.93 (4)	1.76 (4)	2.684 (2)	175 (4)
O11—H11A···O2^vii	0.81 (3)	2.06 (3)	2.849 (2)	166 (3)
O11—H11B···O3^viii	0.83 (3)	2.23 (3)	2.968 (2)	148 (3)
O11—H11B···O1^viii	0.83 (3)	2.25 (3)	2.863 (2)	131 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂F₃N₃O₅S·H₂O
M_r	433.36
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	113
a, b, c (Å)	14.1640 (13), 9.136 (1), 27.459 (3)
V (Å³)	3553.3 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.24 × 0.20 × 0.18

Data collection
Diffractometer	Rigaku Saturn724 CCD
Absorption correction	Multi-scan (CrystalClear-SM Expert; Rigaku, 2009)
T_min, T_max	0.941, 0.956
No. of measured, independent and observed [I > 2σ(I)] reflections	34133, 7861, 7466
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.091, 1.05
No. of reflections	7861
No. of parameters	563
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.27
Absolute structure	Flack (1983), 3539 Friedel pairs
Absolute structure parameter	−0.01 (5)

Computer programs: CrystalClear-SM Expert (Rigaku, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O12—H12A···O6	0.85 (3)	2.28 (3)	2.867 (2)	126 (2)
O12—H12A···O8	0.85 (3)	2.20 (3)	2.949 (2)	147 (3)
O12—H12B···O7ⁱ	0.79 (3)	2.11 (3)	2.852 (2)	156 (3)
N1—H1···O12ⁱⁱ	0.99 (2)	2.00 (2)	2.969 (2)	168.5 (19)
N2—H2···O12ⁱⁱⁱ	0.80 (3)	2.15 (3)	2.905 (2)	159 (2)
N5—H5···O11	0.82 (3)	2.15 (3)	2.903 (2)	153 (3)
N4—H4···O11^iv	0.84 (3)	2.17 (3)	2.991 (2)	166 (2)
O6—H6···O2^v	0.82 (3)	1.86 (3)	2.684 (2)	179 (3)
O1—H1A···O7^vi	0.93 (4)	1.76 (4)	2.684 (2)	175 (4)
O11—H11A···O2^vii	0.81 (3)	2.06 (3)	2.849 (2)	166 (3)
O11—H11B···O3^viii	0.83 (3)	2.23 (3)	2.968 (2)	148 (3)
O11—H11B···O1^viii	0.83 (3)	2.25 (3)	2.863 (2)	131 (3)

Acknowledgements

This work was supported by the Natural Science Foundation of Henan Province, China (grant No. 082300420110) and the Natural Science Foundation of Henan Province Education Department, China (grant No. 2007150036).

References

Brier, S., Lemaire, D., DeBonis, S., Forest, E. & Kozielski, F. (2004). Biochem. 43, 13072–13082. CrossRef 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
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals 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 (2009). CrystalClear-SM Expert and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ulrich, H. (2004). US Patent No. 2 004 033 897. Google Scholar
Zorkun, I. S., Sarac, S., Celebi, S. & Erol, K. (2006). Bioorg. Med. Chem. 14, 8582–8589. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 66| Part 11| November 2010| Pages o2932-o2933

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

rac-6-Hy­dr­oxy-4-(4-nitro­phen­yl)-5-(2-thienyl­carbon­yl)-6-(tri­fluoro­meth­yl)-3,4,5,6-tetra­hydro­pyrimidin-2(1H)-one monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

rac-6-Hydroxy-4-(4-nitrophenyl)-5-(2-thienylcarbonyl)-6-(trifluoromethyl)-3,4,5,6-tetrahydropyrimidin-2(1H)-one monohydrate