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

Mosslemin, M.H.; Nateghi, M.R.; Sadoughi, H.; Lamei, A.

doi:10.1107/S1600536809017097

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1339

doi:10.1107/S1600536809017097

Open

access

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

Mohammad Hossein Mosslemin,^a ^* Mohammad Reza Nateghi,^a Hesamaddin Sadoughi ^a and Asal Lamei ^a

^aDepartment of Chemistry, Islamic Azad University, Yazd Branch, Yazd, Iran
^*Correspondence e-mail: mosleminemh@yahoo.com

(Received 3 May 2009; accepted 6 May 2009; online 20 May 2009)

The asymmetric unit of the title compound, C₁₆H₁₂ClF₃N₂O₃S·H₂O, contains two crystallographically independent organic molecules and two water molecules. The organic species are linked by an intermolecular O—H⋯O hydrogen bond, while the water molecules are connected to them through intermolecular O—H⋯N hydrogen bonds. The thiophene and phenyl rings are oriented at dihedral angles of 62.35 (4) in the first independent molecule and 60.74 (5)° in the second, while the pyrimidine rings adopt twisted conformations in both molecules. Intramolecular N—H⋯F interactions result in the formation of two five-membered rings having envelope conformations. In the crystal structure, further intermolecular O—H⋯O and N—H⋯O hydrogen bonds link the molecules into chains.

Related literature

For related structures, see: Paraskar et al. (2003 ); Peng & Deng (2001 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₆H₁₂ClF₃N₂O₃S·H₂O
M_r = 422.81
Orthorhombic, P b n 2₁
a = 9.1156 (6) Å
b = 14.1582 (7) Å
c = 27.6012 (17) Å
V = 3562.2 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.39 mm⁻¹
T = 298 K
0.5 × 0.3 × 0.2 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ) T_min = 0.860, T_max = 0.923
19595 measured reflections
9251 independent reflections
7478 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.146
S = 1.07
9251 reflections
511 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.47 e Å⁻³
Absolute structure: Flack (1983 ), 4326 Friedel pairs
Flack parameter: 0.18 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯F3	0.86	2.38	2.719 (4)	104
N1—H1A⋯O7ⁱ	0.86	2.37	3.022 (4)	132
N2—H2A⋯O7	0.86	2.15	2.914 (4)	147
O2—H2B⋯O6ⁱⁱ	0.89 (4)	1.85 (4)	2.694 (4)	156 (3)
N3—H3A⋯F4	0.86	2.41	2.733 (4)	103
N3—H3A⋯O8ⁱⁱⁱ	0.86	2.34	3.007 (4)	134
N4—H4A⋯O8	0.86	2.14	2.921 (4)	151
O5—H5⋯O3	0.98 (6)	1.72 (6)	2.686 (4)	169 (6)
O7—H7A⋯O6ⁱⁱⁱ	0.84 (7)	2.27 (7)	2.879 (4)	130 (5)
O7—H7B⋯O4^iv	0.86 (6)	2.36 (6)	2.996 (5)	131 (5)
O7—H7B⋯O5^iv	0.86 (6)	2.18 (6)	2.859 (4)	135 (5)
O8—H8A⋯O3^v	0.75 (5)	2.21 (5)	2.897 (4)	153 (4)
O8—H8B⋯O1ⁱ	0.83 (5)	2.22 (6)	2.968 (5)	150 (5)
O8—H8B⋯O2ⁱ	0.83 (5)	2.27 (6)	2.861 (4)	128 (5)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) x-1, y, z; (iii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ ; (iv) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (v) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809017097/hk2682sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809017097/hk2682Isup2.hkl

checkCIF report

Comment top

In recent years, several modified and improved procedures for one-pot synthesis of dihydropyrimidine-2(1H)-ones have been reported (Paraskar et al., 2003; Peng & Deng, 2001). However, in spite of their potential utility, many of these methods suffer from drawback like longer reaction times, unsatisfactory yields and cumbersome product isolation procedures. We report herein the synthesis and crystal structure of the title compound.

The asymmetric unit of the title compound contains two crystallographically independent molecules and two water molecules (Fig. 1 ), in which the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (S1/C1–C4), C (C11–C16) and D (S2/C17–C20), F (C27–C32) are, of course, planar and they are oriented at dihedral angles of A/C = 62.35 (4)° and D/F = 60.74 (5)°. Rings B (N1/N2/C6/C7/C9/C10) and E (N3/N4/C22/C23/C25/C26) adopt twisted conformations. Intramolecular N—H···F interactions (Table 1) result in the formations of two five-membered rings G (N1/F3/C7/C8/H1A) and H (N3/F4/C23/C24/H3A) having envelope conformations with atoms C8 and C24 displaced by 0.594 (4) and -0.603 (5) Å from the planes of the other rings atoms. Intramolecular O—H···O hydrogen bond (Table 1) link the two molecules, while the water molecules are connected to them through the intramolecular N—H···O hydrogen bonds (Table 1).

In the crystal structure, intermolecular O—H···O and N—H···O hydrogen bonds (Table 1) link the molecules into chains (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For related structures, see: Paraskar et al. (2003); Peng & Deng (2001). For bond-length data, see: Allen et al. (1987).

Experimental top

For the preparation of the title compound, a mixture of 1-(2-thenoyl)-3,3,3-trifluoroacetone (0.222 g, 1 mmol), 4-chlorobenzaldehyde (0.141 g, 1 mmol), urea (0.18 g, 3 mmol) and ammonium chloride (0.005 g, 0.1 mmol) were heated at 373 K under stirring for 20 min. After cooling, the reaction mixture was poured onto crushed ice (20 g). The separated solid was filtered, washed with cold water (20 ml) and recrystallized from ethylacetate–hexane (1:3) to afford pure product (yield; 78%, 0.330 g).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A partial packing diagram of the title compound viewed down the a axis. Hydrogen bonds are shown as dashed lines.

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

Crystal data top

C₁₆H₁₂ClF₃N₂O₃S·H₂O	F(000) = 1728
M_r = 422.81	D_x = 1.577 Mg m⁻³
Orthorhombic, Pbn2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ab	Cell parameters from 1879 reflections
a = 9.1156 (6) Å	θ = 2.4–29.2°
b = 14.1582 (7) Å	µ = 0.39 mm⁻¹
c = 27.6012 (17) Å	T = 298 K
V = 3562.2 (4) Å³	Block, colourless
Z = 8	0.5 × 0.3 × 0.2 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	7478 reflections with I > 2σ(I)
ϕ and ω scans	R_int = 0.032
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	θ_max = 29.2°, θ_min = 2.4°
T_min = 0.860, T_max = 0.923	h = −11→12
19595 measured reflections	k = −19→19
9251 independent reflections	l = −37→36

Refinement top

Refinement on F²	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0679P)² + 1.8489P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.055	(Δ/σ)_max = 0.012
wR(F²) = 0.146	Δρ_max = 0.41 e Å⁻³
S = 1.07	Δρ_min = −0.47 e Å⁻³
9251 reflections	Absolute structure: Flack (1983), 4326 Friedel pairs
511 parameters	Absolute structure parameter: 0.18 (8)

Crystal data top

C₁₆H₁₂ClF₃N₂O₃S·H₂O	V = 3562.2 (4) Å³
M_r = 422.81	Z = 8
Orthorhombic, Pbn2₁	Mo Kα radiation
a = 9.1156 (6) Å	µ = 0.39 mm⁻¹
b = 14.1582 (7) Å	T = 298 K
c = 27.6012 (17) Å	0.5 × 0.3 × 0.2 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	9251 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	7478 reflections with I > 2σ(I)
T_min = 0.860, T_max = 0.923	R_int = 0.032
19595 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.146	Δρ_max = 0.41 e Å⁻³
S = 1.07	Δρ_min = −0.47 e Å⁻³
9251 reflections	Absolute structure: Flack (1983), 4326 Friedel pairs
511 parameters	Absolute structure parameter: 0.18 (8)

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.20863 (18)	1.18591 (11)	0.10132 (6)	0.0800 (4)
Cl2	0.71737 (17)	0.07620 (11)	0.51510 (6)	0.0829 (5)
S1	−0.37400 (15)	0.85338 (12)	0.12927 (6)	0.0797 (4)
S2	0.13318 (16)	0.40572 (12)	0.48988 (7)	0.0805 (4)
O1	−0.2355 (3)	0.8588 (2)	0.22653 (14)	0.0540 (8)
O2	−0.0969 (3)	0.71519 (19)	0.27993 (10)	0.0401 (6)
H2B	−0.086 (4)	0.665 (3)	0.2992 (15)	0.028 (10)*
O3	0.3549 (3)	0.69972 (17)	0.28201 (10)	0.0414 (6)
O4	0.2597 (3)	0.4046 (3)	0.39238 (14)	0.0539 (8)
O5	0.4027 (3)	0.54419 (17)	0.33543 (9)	0.0394 (5)
H5	0.396 (7)	0.604 (4)	0.318 (2)	0.088 (18)*
O6	0.8546 (3)	0.55885 (17)	0.33323 (10)	0.0413 (6)
O7	0.3736 (3)	0.9773 (2)	0.30044 (11)	0.0433 (6)
H7A	0.459 (8)	0.964 (4)	0.309 (2)	0.09 (2)*
H7B	0.321 (7)	0.993 (4)	0.325 (2)	0.080 (18)*
O8	0.8726 (3)	0.2819 (2)	0.31572 (11)	0.0423 (6)
H8A	0.946 (6)	0.278 (3)	0.3038 (17)	0.045 (13)*
H8B	0.820 (6)	0.283 (4)	0.291 (2)	0.066 (15)*
N1	0.1334 (3)	0.66639 (19)	0.24968 (11)	0.0335 (6)
H1A	0.1546	0.6074	0.247	0.04*
N2	0.2184 (4)	0.8206 (2)	0.25512 (13)	0.0408 (7)
H2A	0.291	0.8579	0.2605	0.049*
N3	0.6328 (3)	0.59341 (18)	0.36587 (10)	0.0314 (5)
H3A	0.6543	0.6524	0.3679	0.038*
N4	0.7153 (4)	0.43923 (19)	0.36029 (13)	0.0385 (7)
H4A	0.7864	0.4015	0.3535	0.046*
F1	−0.0306 (3)	0.61345 (17)	0.16413 (9)	0.0574 (6)
F2	−0.2295 (3)	0.6369 (2)	0.20268 (16)	0.0684 (9)
F3	−0.0748 (3)	0.53514 (14)	0.22866 (10)	0.0553 (6)
F4	0.4222 (3)	0.72493 (15)	0.38632 (10)	0.0572 (6)
F5	0.2705 (3)	0.6231 (2)	0.41348 (15)	0.0686 (9)
F6	0.4700 (3)	0.64863 (18)	0.45092 (9)	0.0618 (7)
C1	−0.3412 (9)	0.8435 (4)	0.0706 (3)	0.094 (2)
H1	−0.4133	0.8506	0.047	0.112*
C2	−0.2010 (10)	0.8242 (5)	0.0601 (2)	0.084 (2)
H2	−0.1682	0.8161	0.0285	0.1*
C3	−0.1067 (5)	0.8169 (3)	0.10026 (15)	0.0440 (8)
H3	−0.0063	0.8051	0.0994	0.053*
C4	−0.1978 (4)	0.8318 (3)	0.14442 (15)	0.0426 (8)
C5	−0.1541 (4)	0.8292 (2)	0.19488 (13)	0.0343 (7)
C6	−0.0040 (3)	0.7890 (2)	0.20871 (12)	0.0286 (6)
H6	0.0497	0.7749	0.1788	0.034*
C7	−0.0144 (3)	0.6974 (2)	0.23879 (11)	0.0288 (6)
C8	−0.0881 (4)	0.6194 (2)	0.20873 (13)	0.0366 (7)
C9	0.2396 (3)	0.7281 (3)	0.26401 (15)	0.0311 (7)
C10	0.0830 (4)	0.8633 (2)	0.23712 (12)	0.0314 (6)
H10	0.0241	0.8855	0.2646	0.038*
C11	0.1184 (3)	0.9461 (2)	0.20424 (12)	0.0319 (6)
C12	0.2245 (5)	0.9376 (3)	0.1683 (2)	0.0462 (9)
H12	0.2777	0.8818	0.1655	0.055*
C13	0.2516 (4)	1.0109 (3)	0.13683 (18)	0.0466 (11)
H13	0.3236	1.0052	0.1131	0.056*
C14	0.1722 (4)	1.0921 (3)	0.14066 (14)	0.0453 (8)
C15	0.0667 (5)	1.1025 (3)	0.17562 (15)	0.0461 (9)
H15	0.0139	1.1586	0.178	0.055*
C16	0.0395 (4)	1.0292 (2)	0.20716 (14)	0.0397 (7)
H16	−0.0328	1.0358	0.2307	0.048*
C17	0.1708 (9)	0.4116 (5)	0.5484 (3)	0.088 (2)
H17	0.0997	0.4045	0.5723	0.105*
C18	0.3112 (9)	0.4273 (4)	0.5583 (2)	0.0804 (18)
H18	0.3463	0.4308	0.5899	0.096*
C19	0.4056 (5)	0.4386 (3)	0.51657 (13)	0.0444 (8)
H19	0.506	0.4501	0.5167	0.053*
C20	0.3103 (4)	0.4283 (3)	0.47414 (15)	0.0421 (8)
C21	0.3463 (4)	0.4322 (2)	0.42239 (14)	0.0365 (7)
C22	0.4972 (3)	0.4722 (2)	0.40755 (11)	0.0287 (6)
H22	0.5523	0.4871	0.4371	0.034*
C23	0.4852 (3)	0.5625 (2)	0.37684 (11)	0.0285 (6)
C24	0.4120 (4)	0.6412 (2)	0.40686 (14)	0.0386 (7)
C25	0.7380 (4)	0.5309 (2)	0.35238 (16)	0.0331 (8)
C26	0.5819 (3)	0.3969 (2)	0.37927 (12)	0.0307 (6)
H26	0.5215	0.3742	0.3523	0.037*
C27	0.6181 (3)	0.3148 (2)	0.41269 (12)	0.0307 (6)
C28	0.5391 (4)	0.2319 (2)	0.40975 (14)	0.0401 (7)
H28	0.4665	0.2253	0.3863	0.048*
C29	0.5675 (4)	0.1575 (3)	0.44180 (17)	0.0499 (9)
H29	0.5138	0.1017	0.4402	0.06*
C30	0.6760 (4)	0.1689 (3)	0.47547 (15)	0.0492 (10)
C31	0.7576 (5)	0.2514 (3)	0.4788 (2)	0.0515 (12)
H31	0.8306	0.2575	0.5021	0.062*
C32	0.7287 (4)	0.3237 (3)	0.44722 (16)	0.0398 (8)
H32	0.7833	0.3791	0.4488	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0826 (8)	0.0777 (8)	0.0797 (9)	−0.0138 (7)	0.0002 (8)	0.0486 (7)
Cl2	0.0798 (8)	0.0833 (8)	0.0856 (10)	0.0318 (7)	0.0201 (8)	0.0568 (8)
S1	0.0514 (6)	0.0965 (10)	0.0912 (11)	0.0052 (7)	−0.0265 (7)	0.0229 (8)
S2	0.0571 (7)	0.0907 (10)	0.0937 (11)	−0.0052 (7)	0.0273 (8)	0.0203 (8)
O1	0.0466 (16)	0.0612 (18)	0.054 (2)	0.0213 (13)	0.0096 (13)	0.0121 (15)
O2	0.0436 (14)	0.0339 (12)	0.0427 (14)	0.0050 (11)	0.0152 (11)	0.0097 (11)
O3	0.0324 (12)	0.0356 (12)	0.0561 (16)	−0.0016 (9)	−0.0148 (11)	0.0126 (11)
O4	0.0398 (15)	0.0719 (19)	0.050 (2)	−0.0212 (13)	−0.0117 (12)	0.0137 (15)
O5	0.0443 (13)	0.0339 (12)	0.0400 (13)	−0.0061 (10)	−0.0126 (11)	0.0086 (10)
O6	0.0356 (12)	0.0367 (12)	0.0515 (15)	0.0034 (10)	0.0149 (11)	0.0112 (11)
O7	0.0327 (13)	0.0486 (15)	0.0486 (16)	−0.0070 (11)	0.0040 (11)	−0.0024 (12)
O8	0.0315 (13)	0.0482 (15)	0.0472 (15)	0.0060 (11)	−0.0037 (12)	−0.0004 (12)
N1	0.0298 (12)	0.0255 (12)	0.0451 (17)	0.0001 (10)	−0.0053 (11)	0.0014 (11)
N2	0.0395 (14)	0.0272 (13)	0.056 (2)	−0.0045 (12)	−0.0210 (15)	0.0089 (12)
N3	0.0281 (12)	0.0246 (11)	0.0414 (15)	−0.0004 (9)	0.0072 (11)	0.0021 (10)
N4	0.0399 (14)	0.0280 (12)	0.0475 (18)	0.0089 (12)	0.0166 (14)	0.0047 (11)
F1	0.0750 (16)	0.0529 (13)	0.0443 (13)	−0.0109 (12)	−0.0044 (12)	−0.0085 (11)
F2	0.0333 (11)	0.0598 (15)	0.112 (3)	−0.0091 (11)	−0.0239 (15)	0.0002 (16)
F3	0.0688 (15)	0.0297 (9)	0.0674 (16)	−0.0121 (10)	−0.0203 (13)	0.0055 (10)
F4	0.0739 (16)	0.0313 (10)	0.0664 (16)	0.0138 (10)	0.0233 (13)	0.0062 (10)
F5	0.0312 (10)	0.0600 (15)	0.115 (3)	0.0080 (10)	0.0226 (15)	−0.0060 (16)
F6	0.0785 (18)	0.0637 (14)	0.0433 (13)	0.0138 (13)	0.0042 (12)	−0.0161 (11)
C1	0.115 (5)	0.076 (4)	0.090 (5)	0.007 (4)	−0.071 (4)	0.007 (3)
C2	0.132 (6)	0.077 (4)	0.041 (3)	0.015 (4)	−0.022 (3)	0.003 (2)
C3	0.053 (2)	0.0481 (19)	0.0310 (17)	0.0122 (16)	−0.0079 (16)	0.0067 (15)
C4	0.0383 (18)	0.0404 (17)	0.049 (2)	0.0002 (14)	−0.0079 (15)	0.0121 (16)
C5	0.0302 (15)	0.0331 (15)	0.0397 (18)	0.0016 (12)	0.0018 (12)	0.0065 (13)
C6	0.0256 (13)	0.0301 (13)	0.0302 (15)	−0.0005 (10)	0.0013 (11)	0.0037 (12)
C7	0.0250 (13)	0.0266 (12)	0.0348 (15)	−0.0014 (10)	−0.0003 (11)	0.0006 (11)
C8	0.0340 (15)	0.0332 (15)	0.0427 (18)	−0.0031 (12)	−0.0074 (14)	0.0016 (13)
C9	0.0307 (16)	0.0329 (15)	0.0297 (19)	−0.0014 (12)	−0.0019 (11)	0.0048 (13)
C10	0.0381 (16)	0.0238 (12)	0.0322 (16)	0.0010 (11)	−0.0003 (12)	0.0029 (11)
C11	0.0342 (15)	0.0302 (14)	0.0312 (15)	−0.0020 (11)	−0.0042 (12)	0.0048 (12)
C12	0.0484 (19)	0.0333 (17)	0.057 (3)	0.0017 (15)	0.012 (2)	−0.0047 (16)
C13	0.051 (3)	0.051 (2)	0.037 (3)	−0.0155 (17)	0.0098 (15)	0.0014 (18)
C14	0.0478 (19)	0.0446 (19)	0.0435 (19)	−0.0134 (16)	−0.0069 (16)	0.0182 (16)
C15	0.047 (2)	0.0348 (16)	0.056 (2)	0.0060 (15)	−0.0049 (17)	0.0120 (16)
C16	0.0369 (16)	0.0360 (16)	0.0464 (19)	0.0024 (13)	0.0037 (15)	0.0045 (15)
C17	0.106 (5)	0.074 (4)	0.083 (4)	0.001 (3)	0.059 (4)	0.014 (3)
C18	0.122 (6)	0.070 (3)	0.050 (3)	0.0003 (3)	0.017 (3)	0.015 (2)
C19	0.054 (2)	0.052 (2)	0.0271 (17)	0.0350 (3)	0.0152 (15)	0.0050 (15)
C20	0.0339 (17)	0.0429 (18)	0.050 (2)	0.0030 (14)	0.0108 (15)	0.0132 (15)
C21	0.0302 (15)	0.0361 (15)	0.0431 (18)	−0.0016 (12)	0.0007 (13)	0.0118 (14)
C22	0.0261 (13)	0.0304 (13)	0.0297 (15)	−0.0015 (10)	−0.0009 (11)	0.0030 (11)
C23	0.0252 (13)	0.0282 (13)	0.0321 (15)	−0.0007 (10)	−0.0010 (11)	0.0027 (11)
C24	0.0289 (14)	0.0389 (16)	0.048 (2)	0.0046 (12)	0.0079 (14)	0.0032 (14)
C25	0.0289 (16)	0.0306 (15)	0.040 (2)	0.0029 (11)	0.0083 (12)	0.0042 (14)
C26	0.0335 (14)	0.0278 (13)	0.0309 (15)	−0.0023 (11)	0.0024 (12)	0.0058 (11)
C27	0.0295 (13)	0.0270 (13)	0.0355 (16)	0.0035 (11)	0.0015 (12)	0.0037 (12)
C28	0.0408 (16)	0.0333 (15)	0.046 (2)	−0.0028 (13)	0.0000 (15)	0.0101 (14)
C29	0.047 (2)	0.0364 (17)	0.067 (3)	−0.0020 (15)	0.0094 (19)	0.0194 (17)
C30	0.0469 (19)	0.052 (2)	0.049 (2)	0.0184 (17)	0.0188 (17)	0.0210 (18)
C31	0.053 (3)	0.055 (2)	0.046 (3)	0.0143 (18)	−0.0053 (17)	0.004 (2)
C32	0.0390 (17)	0.0401 (17)	0.040 (2)	0.0013 (14)	−0.0057 (15)	0.0058 (15)

Geometric parameters (Å, º) top

O2—H2B	0.89 (4)	C14—C15	1.370 (6)
O5—H5	0.99 (6)	C14—Cl1	1.747 (4)
O7—H7A	0.84 (7)	C15—C16	1.377 (5)
O7—H7B	0.87 (7)	C15—H15	0.93
O8—H8A	0.75 (5)	C16—H16	0.93
O8—H8B	0.84 (6)	C17—C18	1.328 (11)
N1—H1A	0.86	C17—S2	1.652 (8)
N2—H2A	0.86	C17—H17	0.93
N3—H3A	0.86	C18—C19	1.448 (7)
N4—H4A	0.86	C18—H18	0.93
C1—C2	1.338 (11)	C19—C20	1.465 (6)
C1—S1	1.653 (8)	C19—H19	0.93
C1—H1	0.93	C20—C21	1.467 (5)
C2—C3	1.407 (7)	C20—S2	1.703 (4)
C2—H2	0.93	C21—O4	1.209 (5)
C3—C4	1.490 (6)	C21—C22	1.542 (4)
C3—H3	0.93	C22—C26	1.530 (4)
C4—C5	1.449 (5)	C22—C23	1.538 (4)
C4—S1	1.688 (4)	C22—H22	0.98
C5—O1	1.221 (5)	C23—O5	1.393 (4)
C5—C6	1.530 (4)	C23—N3	1.447 (4)
C6—C10	1.533 (4)	C23—C24	1.541 (4)
C6—C7	1.543 (4)	C24—F4	1.317 (4)
C6—H6	0.98	C24—F5	1.328 (4)
C7—O2	1.385 (4)	C24—F6	1.330 (5)
C7—N1	1.448 (4)	C25—O6	1.252 (4)
C7—C8	1.536 (4)	C25—N4	1.332 (4)
C8—F3	1.319 (4)	C25—N3	1.357 (4)
C8—F2	1.323 (4)	C26—N4	1.453 (4)
C8—F1	1.340 (4)	C26—C27	1.520 (4)
C9—O3	1.230 (4)	C26—H26	0.98
C9—N2	1.347 (4)	C27—C28	1.380 (5)
C9—N1	1.363 (4)	C27—C32	1.393 (5)
C10—N2	1.461 (4)	C28—C29	1.399 (5)
C10—C11	1.517 (4)	C28—H28	0.93
C10—H10	0.98	C29—C30	1.367 (6)
C11—C16	1.382 (5)	C29—H29	0.93
C11—C12	1.391 (5)	C30—C31	1.388 (7)
C12—C13	1.376 (6)	C30—Cl2	1.750 (4)
C12—H12	0.93	C31—C32	1.370 (6)
C13—C14	1.363 (6)	C31—H31	0.93
C13—H13	0.93	C32—H32	0.93

C1—S1—C4	93.2 (3)	C13—C14—C15	121.2 (4)
C17—S2—C20	92.5 (3)	C13—C14—Cl1	119.5 (3)
C7—O2—H2B	107 (3)	C15—C14—Cl1	119.3 (3)
C23—O5—H5	106 (4)	C14—C15—C16	119.4 (3)
H7A—O7—H7B	110 (6)	C14—C15—H15	120.3
H8A—O8—H8B	99 (5)	C16—C15—H15	120.3
C7—N1—H1A	119.1	C15—C16—C11	120.8 (3)
C9—N1—C7	121.8 (3)	C15—C16—H16	119.6
C9—N1—H1A	119.1	C11—C16—H16	119.6
C9—N2—C10	125.9 (3)	C18—C17—S2	114.3 (4)
C9—N2—H2A	117.1	C18—C17—H17	122.9
C10—N2—H2A	117.1	S2—C17—H17	122.9
C23—N3—H3A	119.4	C17—C18—C19	115.2 (5)
C25—N3—C23	121.1 (3)	C17—C18—H18	122.4
C25—N3—H3A	119.4	C19—C18—H18	122.4
C25—N4—C26	126.2 (3)	C18—C19—C20	105.9 (4)
C25—N4—H4A	116.9	C18—C19—H19	127.1
C26—N4—H4A	116.9	C20—C19—H19	127.1
C2—C1—S1	113.7 (4)	C19—C20—C21	130.0 (3)
C2—C1—H1	123.2	C19—C20—S2	112.1 (3)
S1—C1—H1	123.2	C21—C20—S2	117.9 (3)
C1—C2—C3	115.4 (6)	O4—C21—C20	120.6 (3)
C1—C2—H2	122.3	O4—C21—C22	121.3 (3)
C3—C2—H2	122.3	C20—C21—C22	118.2 (3)
C2—C3—C4	107.1 (4)	C26—C22—C23	109.5 (2)
C2—C3—H3	126.5	C26—C22—C21	109.3 (2)
C4—C3—H3	126.5	C23—C22—C21	112.8 (2)
C5—C4—C3	129.0 (3)	C26—C22—H22	108.4
C5—C4—S1	120.3 (3)	C23—C22—H22	108.4
C3—C4—S1	110.7 (3)	C21—C22—H22	108.4
O1—C5—C4	120.8 (3)	O5—C23—N3	112.8 (3)
O1—C5—C6	119.5 (3)	O5—C23—C22	109.6 (2)
C4—C5—C6	119.7 (3)	N3—C23—C22	107.5 (2)
C5—C6—C10	109.6 (2)	O5—C23—C24	110.0 (3)
C5—C6—C7	113.1 (2)	N3—C23—C24	107.3 (2)
C10—C6—C7	109.5 (2)	C22—C23—C24	109.6 (2)
C5—C6—H6	108.2	F4—C24—F5	107.6 (3)
C10—C6—H6	108.2	F4—C24—F6	107.1 (3)
C7—C6—H6	108.2	F5—C24—F6	106.0 (3)
O2—C7—N1	112.9 (3)	F4—C24—C23	112.9 (3)
O2—C7—C8	109.6 (3)	F5—C24—C23	110.8 (3)
N1—C7—C8	107.5 (2)	F6—C24—C23	112.1 (3)
O2—C7—C6	108.8 (2)	O6—C25—N4	120.6 (3)
N1—C7—C6	108.0 (2)	O6—C25—N3	120.6 (3)
C8—C7—C6	109.9 (2)	N4—C25—N3	118.8 (3)
F3—C8—F2	108.2 (3)	N4—C26—C27	110.6 (3)
F3—C8—F1	106.9 (3)	N4—C26—C22	108.6 (2)
F2—C8—F1	106.0 (3)	C27—C26—C22	109.4 (3)
F3—C8—C7	112.7 (3)	N4—C26—H26	109.4
F2—C8—C7	111.0 (3)	C27—C26—H26	109.4
F1—C8—C7	111.7 (3)	C22—C26—H26	109.4
O3—C9—N2	120.9 (3)	C28—C27—C32	119.6 (3)
O3—C9—N1	121.0 (3)	C28—C27—C26	120.1 (3)
N2—C9—N1	118.0 (3)	C32—C27—C26	120.2 (3)
N2—C10—C11	110.1 (3)	C27—C28—C29	120.5 (4)
N2—C10—C6	109.1 (2)	C27—C28—H28	119.8
C11—C10—C6	109.5 (3)	C29—C28—H28	119.8
N2—C10—H10	109.4	C30—C29—C28	118.3 (4)
C11—C10—H10	109.4	C30—C29—H29	120.8
C6—C10—H10	109.4	C28—C29—H29	120.8
C16—C11—C12	118.5 (3)	C29—C30—C31	122.2 (4)
C16—C11—C10	120.8 (3)	C29—C30—Cl2	119.5 (3)
C12—C11—C10	120.5 (3)	C31—C30—Cl2	118.3 (4)
C13—C12—C11	120.6 (4)	C32—C31—C30	118.9 (4)
C13—C12—H12	119.7	C32—C31—H31	120.6
C11—C12—H12	119.7	C30—C31—H31	120.6
C14—C13—C12	119.5 (4)	C31—C32—C27	120.5 (4)
C14—C13—H13	120.3	C31—C32—H32	119.7
C12—C13—H13	120.3	C27—C32—H32	119.7

S1—C1—C2—C3	−0.8 (8)	C26—C22—C23—O5	64.1 (3)
C1—C2—C3—C4	1.3 (7)	C21—C22—C23—O5	−57.8 (3)
C2—C3—C4—C5	178.4 (5)	C26—C22—C23—N3	−58.8 (3)
C2—C3—C4—S1	−1.2 (5)	C21—C22—C23—N3	179.3 (3)
C3—C4—C5—O1	167.1 (4)	C26—C22—C23—C24	−175.1 (3)
S1—C4—C5—O1	−13.2 (5)	C21—C22—C23—C24	63.0 (3)
C3—C4—C5—C6	−12.8 (6)	O5—C23—C24—F4	−71.1 (3)
S1—C4—C5—C6	166.8 (3)	N3—C23—C24—F4	51.9 (4)
O1—C5—C6—C10	−56.5 (4)	C22—C23—C24—F4	168.3 (3)
C4—C5—C6—C10	123.4 (3)	O5—C23—C24—F5	49.6 (4)
O1—C5—C6—C7	65.9 (4)	N3—C23—C24—F5	172.6 (3)
C4—C5—C6—C7	−114.1 (3)	C22—C23—C24—F5	−71.0 (4)
C5—C6—C7—O2	−57.0 (3)	O5—C23—C24—F6	167.8 (3)
C10—C6—C7—O2	65.5 (3)	N3—C23—C24—F6	−69.2 (3)
C5—C6—C7—N1	−179.9 (3)	C22—C23—C24—F6	47.2 (4)
C10—C6—C7—N1	−57.4 (3)	C23—C22—C26—N4	48.8 (3)
C5—C6—C7—C8	63.1 (3)	C21—C22—C26—N4	172.8 (3)
C10—C6—C7—C8	−174.5 (3)	C23—C22—C26—C27	169.7 (2)
O2—C7—C8—F3	−72.8 (4)	C21—C22—C26—C27	−66.3 (3)
N1—C7—C8—F3	50.3 (4)	N4—C26—C27—C28	−136.7 (3)
C6—C7—C8—F3	167.7 (3)	C22—C26—C27—C28	103.7 (4)
O2—C7—C8—F2	48.7 (4)	N4—C26—C27—C32	44.8 (4)
N1—C7—C8—F2	171.8 (3)	C22—C26—C27—C32	−74.8 (4)
C6—C7—C8—F2	−70.8 (4)	C32—C27—C28—C29	1.3 (6)
O2—C7—C8—F1	166.9 (3)	C26—C27—C28—C29	−177.2 (3)
N1—C7—C8—F1	−70.0 (3)	C27—C28—C29—C30	−0.7 (6)
C6—C7—C8—F1	47.3 (3)	C28—C29—C30—C31	0.2 (6)
C5—C6—C10—N2	173.3 (3)	C28—C29—C30—Cl2	−178.4 (3)
C7—C6—C10—N2	48.7 (3)	C29—C30—C31—C32	−0.2 (7)
C5—C6—C10—C11	−66.2 (3)	Cl2—C30—C31—C32	178.4 (3)
C7—C6—C10—C11	169.2 (3)	C30—C31—C32—C27	0.8 (7)
N2—C10—C11—C16	−137.7 (3)	C28—C27—C32—C31	−1.3 (6)
C6—C10—C11—C16	102.4 (4)	C26—C27—C32—C31	177.2 (4)
N2—C10—C11—C12	46.7 (4)	O3—C9—N1—C7	165.8 (4)
C6—C10—C11—C12	−73.2 (4)	N2—C9—N1—C7	−18.2 (5)
C16—C11—C12—C13	1.0 (6)	O2—C7—N1—C9	−77.2 (4)
C10—C11—C12—C13	176.7 (4)	C8—C7—N1—C9	161.8 (3)
C11—C12—C13—C14	−0.9 (7)	C6—C7—N1—C9	43.2 (4)
C12—C13—C14—C15	0.7 (7)	O3—C9—N2—C10	−175.4 (4)
C12—C13—C14—Cl1	179.0 (4)	N1—C9—N2—C10	8.6 (6)
C13—C14—C15—C16	−0.6 (6)	C11—C10—N2—C9	−145.7 (4)
Cl1—C14—C15—C16	−179.0 (3)	C6—C10—N2—C9	−25.5 (5)
C14—C15—C16—C11	0.7 (6)	O6—C25—N3—C23	164.7 (4)
C12—C11—C16—C15	−0.9 (6)	N4—C25—N3—C23	−15.9 (6)
C10—C11—C16—C15	−176.6 (3)	O5—C23—N3—C25	−77.9 (4)
S2—C17—C18—C19	1.3 (7)	C22—C23—N3—C25	43.0 (4)
C17—C18—C19—C20	−0.1 (6)	C24—C23—N3—C25	160.8 (3)
C18—C19—C20—C21	−179.4 (4)	O6—C25—N4—C26	−175.8 (4)
C18—C19—C20—S2	−1.1 (4)	N3—C25—N4—C26	4.8 (7)
C19—C20—C21—O4	165.8 (4)	C27—C26—N4—C25	−142.9 (4)
S2—C20—C21—O4	−12.3 (5)	C22—C26—N4—C25	−22.8 (5)
C19—C20—C21—C22	−14.0 (6)	C2—C1—S1—C4	0.0 (6)
S2—C20—C21—C22	167.8 (2)	C5—C4—S1—C1	−179.0 (4)
O4—C21—C22—C26	−58.9 (4)	C3—C4—S1—C1	0.8 (4)
C20—C21—C22—C26	120.9 (3)	C18—C17—S2—C20	−1.7 (5)
O4—C21—C22—C23	63.1 (4)	C19—C20—S2—C17	1.6 (4)
C20—C21—C22—C23	−117.0 (3)	C21—C20—S2—C17	−179.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···F3	0.86	2.38	2.719 (4)	104
N1—H1A···O7ⁱ	0.86	2.37	3.022 (4)	132
N2—H2A···O7	0.86	2.15	2.914 (4)	147
O2—H2B···O6ⁱⁱ	0.89 (4)	1.85 (4)	2.694 (4)	156 (3)
N3—H3A···F4	0.86	2.41	2.733 (4)	103
N3—H3A···O8ⁱⁱⁱ	0.86	2.34	3.007 (4)	134
N4—H4A···O8	0.86	2.14	2.921 (4)	151
O5—H5···O3	0.98 (6)	1.72 (6)	2.686 (4)	169 (6)
O7—H7A···O6ⁱⁱⁱ	0.84 (7)	2.27 (7)	2.879 (4)	130 (5)
O7—H7B···O4^iv	0.86 (6)	2.36 (6)	2.996 (5)	131 (5)
O7—H7B···O5^iv	0.86 (6)	2.18 (6)	2.859 (4)	135 (5)
O8—H8A···O3^v	0.75 (5)	2.21 (5)	2.897 (4)	153 (4)
O8—H8B···O1ⁱ	0.83 (5)	2.22 (6)	2.968 (5)	150 (5)
O8—H8B···O2ⁱ	0.83 (5)	2.27 (6)	2.861 (4)	128 (5)

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂ClF₃N₂O₃S·H₂O
M_r	422.81
Crystal system, space group	Orthorhombic, Pbn2₁
Temperature (K)	298
a, b, c (Å)	9.1156 (6), 14.1582 (7), 27.6012 (17)
V (Å³)	3562.2 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.39
Crystal size (mm)	0.5 × 0.3 × 0.2

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1998)
T_min, T_max	0.860, 0.923
No. of measured, independent and observed [I > 2σ(I)] reflections	19595, 9251, 7478
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.686

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.146, 1.07
No. of reflections	9251
No. of parameters	511
No. of restraints	?
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.47
Absolute structure	Flack (1983), 4326 Friedel pairs
Absolute structure parameter	0.18 (8)

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXTL (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···F3	0.86	2.38	2.719 (4)	104
N1—H1A···O7ⁱ	0.86	2.37	3.022 (4)	132
N2—H2A···O7	0.86	2.15	2.914 (4)	147
O2—H2B···O6ⁱⁱ	0.89 (4)	1.85 (4)	2.694 (4)	156 (3)
N3—H3A···F4	0.86	2.41	2.733 (4)	103
N3—H3A···O8ⁱⁱⁱ	0.86	2.34	3.007 (4)	134
N4—H4A···O8	0.86	2.14	2.921 (4)	151
O5—H5···O3	0.98 (6)	1.72 (6)	2.686 (4)	169 (6)
O7—H7A···O6ⁱⁱⁱ	0.84 (7)	2.27 (7)	2.879 (4)	130 (5)
O7—H7B···O4^iv	0.86 (6)	2.36 (6)	2.996 (5)	131 (5)
O7—H7B···O5^iv	0.86 (6)	2.18 (6)	2.859 (4)	135 (5)
O8—H8A···O3^v	0.75 (5)	2.21 (5)	2.897 (4)	153 (4)
O8—H8B···O1ⁱ	0.83 (5)	2.22 (6)	2.968 (5)	150 (5)
O8—H8B···O2ⁱ	0.83 (5)	2.27 (6)	2.861 (4)	128 (5)

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

Acknowledgements

The authors are grateful to Islamic Azad University, Yazd Branch, for financial support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (1998). SMART and SAINT. Bruker AXS, Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Paraskar, A. S., Dewkar, G. K. & Sudalai, A. (2003). Tetrahedron Lett. 44, 3305–3308. Web of Science CrossRef CAS Google Scholar
Peng, J. & Deng, Y. (2001). Tetrahedron Lett. 42, 5917–5919. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1998). SADABS. Bruker AXS, Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1339

doi:10.1107/S1600536809017097

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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