Ethyl 6-(4-fluoro­phen­yl)-4-hy­droxy-2-sulfanyl­idene-4-trifluoro­methyl-1,3-diazinane-5-carboxyl­ate

Huang, B.-J.; Zhu, L.; He, Q.

doi:10.1107/S1600536812007465

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o880

doi:10.1107/S1600536812007465

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Ethyl 6-(4-fluorophenyl)-4-hydroxy-2-sulfanylidene-4-trifluoromethyl-1,3-diazinane-5-carboxylate

Bao-Jun Huang,^a ^* Lei Zhu ^b and Qin He ^b

^aInstitute of Surface Micro and Nano Materials, Xuchang University, Xuchang, Henan Province 461000, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Xuchang University, Xuchang, Henan Province 461000, People's Republic of China
^*Correspondence e-mail: huangbaojun77@yahoo.com.cn

(Received 26 December 2011; accepted 19 February 2012; online 29 February 2012)

In the title compound, C₁₄H₁₄F₄N₂O₃S, the hexahydropyrimidine ring adopts a half-chair conformation. The molecular conformation is stabilized by an intramolecular O—H⋯O hydrogen bond, generating an S(6) ring. The crystal structure features O—H⋯S and N—H⋯S hydrogen bonds.

Related literature

For the bioactivity of dihydropyrimidines, see: Atwal et al. (1989 ); Kappe et al. (1997 ); Brier et al. (2004 ); Cochran et al. (2005 ). For the bioactivity of organofluorine compounds, see: Konz (1997 ); Hass (2004 ). For a related structure, see: Li et al. (2011 ).

Experimental

Crystal data

C₁₄H₁₄F₄N₂O₃S
M_r = 366.33
Monoclinic, P 2₁ /c
a = 11.0091 (12) Å
b = 9.9741 (10) Å
c = 14.6890 (16) Å
β = 109.269 (12)°
V = 1522.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 113 K
0.20 × 0.19 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2009 ) T_min = 0.947, T_max = 0.968
18960 measured reflections
3627 independent reflections
2979 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.084
S = 1.01
3627 reflections
227 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.84	2.06	2.7767 (13)	144
O1—H1⋯S1ⁱ	0.84	2.83	3.3796 (10)	124
N1—H1A⋯S1ⁱⁱ	0.835 (16)	2.635 (17)	3.4566 (12)	168.1 (15)
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+2, -y+1, -z.

Data collection: CrystalClear (Rigaku, 2009); 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: CrystalStructure (Rigaku, 2009).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812007465/fj2501sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812007465/fj2501Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812007465/fj2501Isup3.cml

checkCIF report

Comment top

Dihydropyrimidine (DHPM) derivatives can be used as potential calcium channel blockers, antihypertensive agents, and α1–1 - a-antagonists (Atwal et al., 1989; Kappe et al., 1997;), inhibitors of mitotic kinesin Eg5 for treating cancer (Cochran et al., 2005; Brier et al., 2004). In addition, compounds that contain fluorine have special bioactivity, e.g. flumioxazin is a widely used herbicide (Konz, 1997; Hass, 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 C₁₄H₁₄F₄N₂O₃S (I) was isolated and the structure confirmed by X-ray diffraction.

In the structure of the title molecule, the hexahydropyrimidine ring adopts a half-chair conformation, the mean planes formed by the ring atoms excluding the C atom bonded to the ethoxy carbonyl group have r.m.s. deviations of 0.0348 Å, the dihedral angle between the mean planes and benzenes ring is 58.18 (5)°. The molecular conformation is stabilized by intramolecular O—H···O hydrogen bond, generating an S(6) ring. The crystal structure is stabilized by intermolecular O—H···S and N—H···S hydrogen bonds. For a crystal structure related to the title compound, see: Li et al. (2011).

Related literature top

For the bioactivity of dihydropyrimidines, see: Atwal et al. (1989); Kappe et al. (1997); Brier et al. (2004); Cochran et al. (2005). For the bioactivity of organofluorine compounds, see: Konz (1997); Hass (2004). For a related structure, see: Li et al. (2011).

Experimental top

The title compound was synthesized refluxing for 3 h a stirred solution of 4-fluorobenzaldehyde (2.48 g, 20 mmol), ethyl 4,4,4-trifluoro-3-oxobutanoate(4.42 g, 24 mmol) and thiourea (2.28 g, 30 mmol) in 20 ml of anhydrous ethanol, the reaction catalyzed by sulfamic acid (0.6 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.

Computing details top

Data collection: CrystalClear (Rigaku, 2009); cell refinement: CrystalClear (Rigaku, 2009); data reduction: CrystalClear (Rigaku, 2009); 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: 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.

Ethyl 6-(4-fluorophenyl)-4-hydroxy-2-sulfanylidene-4-trifluoromethyl- 1,3-diazinane-5-carboxylate top

Crystal data top

C₁₄H₁₄F₄N₂O₃S	F(000) = 752
M_r = 366.33	D_x = 1.598 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5440 reflections
a = 11.0091 (12) Å	θ = 2.0–27.9°
b = 9.9741 (10) Å	µ = 0.27 mm⁻¹
c = 14.6890 (16) Å	T = 113 K
β = 109.269 (12)°	Prism, colorless
V = 1522.6 (3) Å³	0.20 × 0.19 × 0.12 mm
Z = 4

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3627 independent reflections
Radiation source: rotating anode	2979 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.042
Detector resolution: 14.63 pixels mm^-1	θ_max = 27.9°, θ_min = 2.0°
ω and ϕ scans	h = −14→13
Absorption correction: multi-scan (CrystalClear; Rigaku, 2009)	k = −13→13
T_min = 0.947, T_max = 0.968	l = −19→18
18960 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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.050P)²] where P = (F_o² + 2F_c²)/3
3627 reflections	(Δ/σ)_max = 0.001
227 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₄H₁₄F₄N₂O₃S	V = 1522.6 (3) Å³
M_r = 366.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.0091 (12) Å	µ = 0.27 mm⁻¹
b = 9.9741 (10) Å	T = 113 K
c = 14.6890 (16) Å	0.20 × 0.19 × 0.12 mm
β = 109.269 (12)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3627 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2009)	2979 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.968	R_int = 0.042
18960 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.44 e Å⁻³
3627 reflections	Δρ_min = −0.27 e Å⁻³
227 parameters

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	1.09867 (3)	0.59272 (4)	0.13111 (2)	0.01692 (10)
F1	0.63627 (8)	0.49595 (8)	−0.01023 (6)	0.0223 (2)
F2	0.70354 (8)	0.30439 (8)	−0.04289 (6)	0.0208 (2)
F3	0.56928 (7)	0.31300 (9)	0.03576 (6)	0.0211 (2)
F4	0.77930 (9)	0.74276 (9)	0.59153 (6)	0.0287 (2)
O1	0.81420 (9)	0.24372 (9)	0.15081 (7)	0.0161 (2)
H1	0.7778	0.2236	0.1910	0.024*
O2	0.64286 (9)	0.28689 (10)	0.25049 (7)	0.0214 (2)
O3	0.55299 (9)	0.49304 (10)	0.22282 (7)	0.0200 (2)
N1	0.89236 (10)	0.43819 (12)	0.10096 (8)	0.0139 (2)
N2	0.96704 (11)	0.54349 (13)	0.24822 (8)	0.0156 (2)
C1	0.97865 (12)	0.52093 (13)	0.16191 (9)	0.0138 (3)
C2	0.78397 (12)	0.37743 (13)	0.12011 (9)	0.0131 (3)
C3	0.67215 (13)	0.37300 (14)	0.02481 (10)	0.0159 (3)
C4	0.74924 (12)	0.46406 (13)	0.19506 (9)	0.0132 (3)
H4	0.7220	0.5551	0.1673	0.016*
C5	0.64259 (13)	0.40290 (14)	0.22563 (9)	0.0154 (3)
C6	0.44550 (14)	0.44909 (18)	0.25374 (11)	0.0270 (4)
H6A	0.4297	0.3523	0.2400	0.032*
H6B	0.3666	0.4985	0.2169	0.032*
C7	0.47442 (16)	0.47361 (19)	0.35960 (12)	0.0333 (4)
H7A	0.5492	0.4200	0.3963	0.050*
H7B	0.3998	0.4479	0.3781	0.050*
H7C	0.4931	0.5689	0.3736	0.050*
C8	0.87196 (12)	0.47696 (14)	0.28305 (9)	0.0138 (3)
H8	0.9039	0.3849	0.3058	0.017*
C9	0.85100 (12)	0.55238 (14)	0.36593 (9)	0.0136 (3)
C10	0.84025 (13)	0.47892 (14)	0.44373 (10)	0.0160 (3)
H10	0.8506	0.3843	0.4449	0.019*
C11	0.81454 (13)	0.54231 (15)	0.51951 (10)	0.0174 (3)
H11	0.8055	0.4924	0.5720	0.021*
C12	0.80260 (13)	0.67954 (15)	0.51632 (10)	0.0183 (3)
C13	0.81342 (14)	0.75668 (15)	0.44131 (10)	0.0216 (3)
H13	0.8051	0.8515	0.4417	0.026*
C14	0.83700 (14)	0.69099 (14)	0.36509 (10)	0.0184 (3)
H14	0.8436	0.7414	0.3120	0.022*
H2A	1.0172 (14)	0.5927 (16)	0.2825 (11)	0.015 (4)*
H1A	0.9054 (15)	0.4242 (17)	0.0489 (12)	0.026 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01646 (18)	0.01854 (18)	0.01832 (18)	−0.00502 (13)	0.00919 (14)	−0.00420 (14)
F1	0.0232 (4)	0.0197 (5)	0.0198 (4)	0.0034 (3)	0.0016 (3)	0.0036 (3)
F2	0.0202 (4)	0.0267 (5)	0.0166 (4)	−0.0024 (3)	0.0075 (3)	−0.0088 (3)
F3	0.0137 (4)	0.0288 (5)	0.0210 (4)	−0.0066 (3)	0.0061 (3)	−0.0033 (4)
F4	0.0441 (6)	0.0261 (5)	0.0230 (5)	−0.0029 (4)	0.0206 (4)	−0.0098 (4)
O1	0.0198 (5)	0.0124 (5)	0.0183 (5)	0.0014 (4)	0.0093 (4)	0.0014 (4)
O2	0.0211 (5)	0.0190 (5)	0.0266 (6)	−0.0008 (4)	0.0114 (4)	0.0025 (4)
O3	0.0160 (5)	0.0229 (6)	0.0235 (5)	0.0035 (4)	0.0097 (4)	0.0004 (4)
N1	0.0138 (6)	0.0172 (6)	0.0128 (6)	−0.0028 (4)	0.0071 (5)	−0.0034 (5)
N2	0.0146 (6)	0.0196 (6)	0.0125 (6)	−0.0063 (5)	0.0044 (5)	−0.0045 (5)
C1	0.0134 (7)	0.0128 (6)	0.0149 (7)	0.0019 (5)	0.0044 (5)	−0.0002 (5)
C2	0.0131 (6)	0.0126 (7)	0.0148 (6)	−0.0001 (5)	0.0061 (5)	−0.0005 (5)
C3	0.0157 (7)	0.0160 (7)	0.0178 (7)	−0.0005 (5)	0.0078 (6)	−0.0022 (5)
C4	0.0141 (7)	0.0137 (6)	0.0124 (6)	0.0007 (5)	0.0054 (5)	−0.0006 (5)
C5	0.0143 (7)	0.0185 (7)	0.0127 (6)	−0.0006 (5)	0.0034 (5)	−0.0025 (5)
C6	0.0152 (7)	0.0367 (9)	0.0330 (9)	0.0005 (6)	0.0133 (7)	−0.0020 (7)
C7	0.0292 (9)	0.0453 (11)	0.0317 (9)	0.0066 (8)	0.0185 (8)	0.0055 (8)
C8	0.0134 (6)	0.0149 (7)	0.0134 (6)	−0.0005 (5)	0.0049 (5)	0.0000 (5)
C9	0.0109 (6)	0.0158 (7)	0.0133 (6)	−0.0016 (5)	0.0028 (5)	−0.0013 (5)
C10	0.0170 (7)	0.0141 (7)	0.0166 (7)	−0.0004 (5)	0.0051 (5)	0.0002 (5)
C11	0.0181 (7)	0.0222 (7)	0.0129 (6)	−0.0017 (6)	0.0064 (6)	0.0023 (6)
C12	0.0202 (7)	0.0217 (8)	0.0152 (7)	−0.0024 (6)	0.0092 (6)	−0.0064 (6)
C13	0.0294 (8)	0.0133 (7)	0.0243 (8)	−0.0019 (6)	0.0119 (6)	−0.0028 (6)
C14	0.0242 (8)	0.0161 (7)	0.0169 (7)	−0.0020 (6)	0.0097 (6)	0.0009 (6)

Geometric parameters (Å, º) top

S1—C1	1.6905 (13)	C4—H4	1.0000
F1—C3	1.3381 (16)	C6—C7	1.501 (2)
F2—C3	1.3428 (15)	C6—H6A	0.9900
F3—C3	1.3367 (15)	C6—H6B	0.9900
F4—C12	1.3678 (15)	C7—H7A	0.9800
O1—C2	1.4120 (15)	C7—H7B	0.9800
O1—H1	0.8400	C7—H7C	0.9800
O2—C5	1.2130 (16)	C8—C9	1.5122 (18)
O3—C5	1.3252 (16)	C8—H8	1.0000
O3—C6	1.4675 (16)	C9—C14	1.3906 (19)
N1—C1	1.3504 (17)	C9—C10	1.3950 (18)
N1—C2	1.4462 (16)	C10—C11	1.3881 (19)
N1—H1A	0.835 (16)	C10—H10	0.9500
N2—C1	1.3345 (17)	C11—C12	1.374 (2)
N2—C8	1.4668 (16)	C11—H11	0.9500
N2—H2A	0.785 (16)	C12—C13	1.381 (2)
C2—C3	1.5296 (18)	C13—C14	1.3936 (19)
C2—C4	1.5436 (17)	C13—H13	0.9500
C4—C5	1.5167 (18)	C14—H14	0.9500
C4—C8	1.5363 (18)

C2—O1—H1	109.5	C7—C6—H6A	109.5
C5—O3—C6	117.11 (11)	O3—C6—H6B	109.5
C1—N1—C2	124.90 (11)	C7—C6—H6B	109.5
C1—N1—H1A	114.4 (11)	H6A—C6—H6B	108.1
C2—N1—H1A	120.7 (11)	C6—C7—H7A	109.5
C1—N2—C8	123.93 (12)	C6—C7—H7B	109.5
C1—N2—H2A	116.6 (10)	H7A—C7—H7B	109.5
C8—N2—H2A	119.4 (10)	C6—C7—H7C	109.5
N2—C1—N1	117.77 (12)	H7A—C7—H7C	109.5
N2—C1—S1	120.74 (10)	H7B—C7—H7C	109.5
N1—C1—S1	121.49 (10)	N2—C8—C9	111.83 (11)
O1—C2—N1	109.59 (10)	N2—C8—C4	105.97 (10)
O1—C2—C3	107.38 (11)	C9—C8—C4	113.17 (10)
N1—C2—C3	107.50 (10)	N2—C8—H8	108.6
O1—C2—C4	112.87 (10)	C9—C8—H8	108.6
N1—C2—C4	108.58 (11)	C4—C8—H8	108.6
C3—C2—C4	110.79 (10)	C14—C9—C10	119.37 (13)
F3—C3—F1	107.59 (10)	C14—C9—C8	122.23 (12)
F3—C3—F2	107.24 (11)	C10—C9—C8	118.35 (12)
F1—C3—F2	107.32 (11)	C11—C10—C9	120.83 (13)
F3—C3—C2	111.15 (10)	C11—C10—H10	119.6
F1—C3—C2	111.82 (11)	C9—C10—H10	119.6
F2—C3—C2	111.49 (10)	C12—C11—C10	117.96 (13)
C5—C4—C8	109.66 (10)	C12—C11—H11	121.0
C5—C4—C2	112.60 (11)	C10—C11—H11	121.0
C8—C4—C2	106.91 (10)	F4—C12—C11	118.22 (12)
C5—C4—H4	109.2	F4—C12—C13	118.43 (13)
C8—C4—H4	109.2	C11—C12—C13	123.34 (13)
C2—C4—H4	109.2	C12—C13—C14	117.84 (14)
O2—C5—O3	125.76 (12)	C12—C13—H13	121.1
O2—C5—C4	123.20 (12)	C14—C13—H13	121.1
O3—C5—C4	111.03 (11)	C9—C14—C13	120.64 (13)
O3—C6—C7	110.79 (13)	C9—C14—H14	119.7
O3—C6—H6A	109.5	C13—C14—H14	119.7

C8—N2—C1—N1	4.3 (2)	C2—C4—C5—O2	49.06 (18)
C8—N2—C1—S1	−175.06 (10)	C8—C4—C5—O3	109.10 (13)
C2—N1—C1—N2	3.4 (2)	C2—C4—C5—O3	−132.01 (12)
C2—N1—C1—S1	−177.24 (10)	C5—O3—C6—C7	91.06 (16)
C1—N1—C2—O1	−99.95 (14)	C1—N2—C8—C9	−161.16 (12)
C1—N1—C2—C3	143.65 (13)	C1—N2—C8—C4	−37.41 (17)
C1—N1—C2—C4	23.75 (17)	C5—C4—C8—N2	−176.87 (11)
O1—C2—C3—F3	59.68 (13)	C2—C4—C8—N2	60.79 (13)
N1—C2—C3—F3	177.53 (10)	C5—C4—C8—C9	−53.96 (15)
C4—C2—C3—F3	−63.98 (14)	C2—C4—C8—C9	−176.31 (10)
O1—C2—C3—F1	179.95 (10)	N2—C8—C9—C14	44.36 (17)
N1—C2—C3—F1	−62.21 (13)	C4—C8—C9—C14	−75.23 (16)
C4—C2—C3—F1	56.28 (14)	N2—C8—C9—C10	−138.31 (12)
O1—C2—C3—F2	−59.90 (13)	C4—C8—C9—C10	102.10 (14)
N1—C2—C3—F2	57.94 (14)	C14—C9—C10—C11	0.66 (19)
C4—C2—C3—F2	176.43 (10)	C8—C9—C10—C11	−176.75 (12)
O1—C2—C4—C5	−54.01 (14)	C9—C10—C11—C12	−1.3 (2)
N1—C2—C4—C5	−175.72 (10)	C10—C11—C12—F4	−178.98 (12)
C3—C2—C4—C5	66.45 (14)	C10—C11—C12—C13	0.8 (2)
O1—C2—C4—C8	66.48 (13)	F4—C12—C13—C14	−179.92 (13)
N1—C2—C4—C8	−55.23 (13)	C11—C12—C13—C14	0.3 (2)
C3—C2—C4—C8	−173.07 (10)	C10—C9—C14—C13	0.5 (2)
C6—O3—C5—O2	0.9 (2)	C8—C9—C14—C13	177.79 (13)
C6—O3—C5—C4	−178.03 (11)	C12—C13—C14—C9	−1.0 (2)
C8—C4—C5—O2	−69.83 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.84	2.06	2.7767 (13)	144
O1—H1···S1ⁱ	0.84	2.83	3.3796 (10)	124
N1—H1A···S1ⁱⁱ	0.835 (16)	2.635 (17)	3.4566 (12)	168.1 (15)

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₄F₄N₂O₃S
M_r	366.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	11.0091 (12), 9.9741 (10), 14.6890 (16)
β (°)	109.269 (12)
V (Å³)	1522.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.20 × 0.19 × 0.12

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2009)
T_min, T_max	0.947, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	18960, 3627, 2979
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.659

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.084, 1.01
No. of reflections	3627
No. of parameters	227
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.27

Computer programs: CrystalClear (Rigaku, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), CrystalStructure (Rigaku, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.84	2.06	2.7767 (13)	144
O1—H1···S1ⁱ	0.84	2.83	3.3796 (10)	124
N1—H1A···S1ⁱⁱ	0.835 (16)	2.635 (17)	3.4566 (12)	168.1 (15)

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

Acknowledgements

This work was supported by the Foundation of Henan Province Education Committee, China (grant Nos. 2010B150026, 2009B150023).

References

Atwal, K. S., Rovnyak, G. C., O'Reilly, B. C. & Schwartz, J. (1989). J. Org. Chem. 54, 5898–5907. CrossRef CAS Web of Science Google Scholar
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
Hass, U. H. (2004). US Patent No. 2 004 033 897. Google Scholar
Kappe, C. O., Fabian, W. M. F. & Semones, M. A. (1997). Tetrahedron, 53, 2803–2816. CSD CrossRef CAS Google Scholar
Konz, M. J. (1997). US Patent No. 5 683 966. Google Scholar
Li, G.-C., Wu, C.-Z., Guo, L.-L. & Yang, F.-L. (2011). Acta Cryst. E67, o1704–o1705. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (2009). CrystalClear 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

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Volume 68| Part 3| March 2012| Page o880

doi:10.1107/S1600536812007465

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

Ethyl 6-(4-fluoro­phen­yl)-4-hy­dr­oxy-2-sulfanyl­­idene-4-tri­fluoro­methyl-1,3-diazinane-5-carboxyl­ate

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References

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Ethyl 6-(4-fluorophenyl)-4-hydroxy-2-sulfanylidene-4-trifluoromethyl-1,3-diazinane-5-carboxylate