tert-Butyl N-[3-hy-droxy-1-phenyl-4-(pyrimidin-2-ylsulfan-yl)butan-2-yl]carbamate monohydrate.

In the title hydrate, C(19)H(25)N(3)O(3)S·H(2)O, the configuration at each chiral centre in the organic mol-ecule is S, with the hy-droxy and carbamate substituents being anti [O-C-C-N torsion angle = -179.3 (3)°]. The thio-pyrimidyl and carbamate residues lie to one side of the pseudo-mirror plane defined by the C(5)S backbone of the mol-ecule; this plane approximately bis-ects the benzene ring at the 1- and 4-C atoms. The dihedral angle formed between the terminal rings is 5.06 (18)°. In the crystal, supra-molecular tubes aligned along the b axis are found: these are sustained by a combination of O-H⋯O, O-H⋯N and N-H⋯O hydrogen bonds.

Related literature

For background to the use of hy­droxy­ethyl­amine derivatives in medicinal chemistry, see: Brik & Wong (2003 ▶); Ghosh et al. (2001 ▶); Marcin et al. (2011 ▶); Trudel et al. (2008 ▶); Cunico et al. (2009a ▶,b ▶,c ▶, 2011 ▶).

Experimental

Crystal data

C19H25N3O3S·H2O

M = 393.50

Monoclinic,

a = 19.4238 (7) Å

b = 5.1275 (2) Å

c = 22.4815 (8) Å

β = 114.319 (2)°

V = 2040.38 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 120 K

0.30 × 0.02 × 0.02 mm

Data collection

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.801, T max = 1.000

11781 measured reflections

4032 independent reflections

3409 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.112

S = 1.04

4032 reflections

259 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.26 e Å−3

Absolute structure: Flack (1983 ▶), 1442 Friedel pairs

Flack parameter: 0.11 (11)

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811031850/hb6348sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031850/hb6348Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811031850/hb6348Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H25N3O3S·H2O	F(000) = 840
Mr = 393.50	Dx = 1.281 Mg m−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 31450 reflections
a = 19.4238 (7) Å	θ = 2.9–27.5°
b = 5.1275 (2) Å	µ = 0.19 mm−1
c = 22.4815 (8) Å	T = 120 K
β = 114.319 (2)°	Needle, colourless
V = 2040.38 (13) Å3	0.30 × 0.02 × 0.02 mm
Z = 4

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer	4032 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	3409 reflections with I > 2σ(I)
graphite	Rint = 0.048
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 2.9°
φ and ω scans	h = −24→24
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −6→5
Tmin = 0.801, Tmax = 1.000	l = −29→28
11781 measured reflections

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)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.112	w = 1/[σ2(Fo2) + (0.0169P)2 + 4.9933P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
4032 reflections	Δρmax = 0.27 e Å−3
259 parameters	Δρmin = −0.26 e Å−3
6 restraints	Absolute structure: Flack (1983), 1442 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.11 (11)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

	x	y	z	Uiso*/Ueq
S1	0.38657 (5)	0.93234 (19)	0.94519 (4)	0.0274 (2)
O1	0.51141 (12)	0.8689 (5)	0.89189 (11)	0.0260 (6)
H1O	0.526 (2)	1.023 (3)	0.898 (2)	0.039*
O2	0.33859 (13)	0.2943 (4)	0.71553 (11)	0.0262 (6)
O3	0.25342 (12)	0.5902 (4)	0.64894 (11)	0.0230 (5)
N1	0.29924 (15)	1.2998 (6)	0.95196 (13)	0.0263 (7)
N2	0.27041 (16)	1.1435 (6)	0.84405 (13)	0.0274 (7)
N3	0.35124 (14)	0.7325 (5)	0.73525 (13)	0.0195 (6)
H3N	0.3325 (17)	0.881 (3)	0.7189 (14)	0.023*
C1	0.43449 (16)	0.8764 (7)	0.84546 (14)	0.0212 (7)
H1	0.4184	1.0614	0.8337	0.025*
C2	0.38603 (18)	0.7501 (7)	0.87609 (15)	0.0247 (7)
H2A	0.4049	0.5714	0.8905	0.030*
H2B	0.3334	0.7358	0.8428	0.030*
C3	0.31002 (17)	1.1467 (7)	0.90796 (16)	0.0228 (7)
C4	0.24166 (18)	1.4693 (7)	0.92708 (16)	0.0300 (8)
H4	0.2315	1.5825	0.9560	0.036*
C5	0.19690 (19)	1.4849 (8)	0.86141 (17)	0.0337 (9)
H5	0.1561	1.6048	0.8445	0.040*
C6	0.21382 (19)	1.3195 (8)	0.82139 (17)	0.0324 (9)
H6	0.1844	1.3292	0.7757	0.039*
C7	0.42887 (16)	0.7273 (7)	0.78451 (14)	0.0203 (7)
H7	0.4438	0.5418	0.7969	0.024*
C8	0.31684 (17)	0.5180 (6)	0.70118 (15)	0.0187 (7)
C9	0.20689 (17)	0.3927 (7)	0.60200 (15)	0.0232 (7)
C10	0.16727 (19)	0.2235 (7)	0.63384 (17)	0.0282 (8)
H10A	0.1391	0.3348	0.6514	0.042*
H10B	0.2049	0.1222	0.6693	0.042*
H10C	0.1323	0.1045	0.6013	0.042*
C11	0.15008 (19)	0.5600 (7)	0.54834 (17)	0.0292 (8)
H11A	0.1767	0.6684	0.5286	0.044*
H11B	0.1231	0.6722	0.5669	0.044*
H11C	0.1138	0.4472	0.5149	0.044*
C12	0.25420 (18)	0.2360 (7)	0.57476 (16)	0.0260 (8)
H12A	0.2829	0.1024	0.6064	0.039*
H12B	0.2892	0.3529	0.5665	0.039*
H12C	0.2208	0.1520	0.5338	0.039*
C13	0.48159 (17)	0.8439 (7)	0.75607 (15)	0.0241 (7)
H13A	0.4615	1.0151	0.7361	0.029*
H13B	0.5320	0.8734	0.7919	0.029*
C14	0.48983 (18)	0.6690 (7)	0.70518 (16)	0.0227 (7)
C15	0.44298 (19)	0.6935 (7)	0.63926 (16)	0.0274 (8)
H15	0.4064	0.8291	0.6250	0.033*
C16	0.44908 (19)	0.5222 (7)	0.59414 (17)	0.0298 (8)
H16	0.4163	0.5397	0.5492	0.036*
C17	0.50219 (19)	0.3270 (8)	0.61384 (17)	0.0316 (8)
H17	0.5059	0.2091	0.5827	0.038*
C18	0.55023 (19)	0.3022 (7)	0.67897 (18)	0.0321 (8)
H18	0.5876	0.1693	0.6926	0.038*
C19	0.54376 (18)	0.4719 (7)	0.72444 (17)	0.0279 (8)
H19	0.5766	0.4532	0.7693	0.033*
O1W	0.58202 (13)	0.3603 (5)	0.91425 (12)	0.0322 (6)
H1W	0.6181 (15)	0.351 (8)	0.9517 (9)	0.048*
H2W	0.561 (2)	0.506 (4)	0.912 (2)	0.048*

	U11	U22	U33	U12	U13	U23
S1	0.0276 (4)	0.0302 (5)	0.0216 (4)	0.0040 (4)	0.0071 (3)	−0.0014 (4)
O1	0.0206 (11)	0.0223 (15)	0.0251 (11)	−0.0019 (10)	−0.0008 (9)	−0.0033 (10)
O2	0.0275 (12)	0.0122 (13)	0.0316 (13)	0.0011 (10)	0.0048 (10)	0.0004 (10)
O3	0.0217 (11)	0.0167 (12)	0.0227 (12)	0.0003 (9)	0.0010 (9)	−0.0035 (10)
N1	0.0276 (14)	0.0291 (18)	0.0228 (14)	−0.0027 (13)	0.0111 (12)	−0.0029 (13)
N2	0.0272 (15)	0.0315 (18)	0.0207 (14)	−0.0017 (13)	0.0071 (12)	0.0004 (13)
N3	0.0167 (13)	0.0118 (14)	0.0244 (14)	−0.0006 (11)	0.0028 (11)	0.0003 (12)
C1	0.0180 (14)	0.0200 (19)	0.0212 (15)	0.0024 (13)	0.0037 (12)	−0.0025 (13)
C2	0.0270 (17)	0.0200 (19)	0.0257 (17)	−0.0012 (14)	0.0093 (14)	−0.0035 (15)
C3	0.0209 (16)	0.023 (2)	0.0247 (17)	−0.0023 (14)	0.0099 (14)	−0.0002 (15)
C4	0.0286 (17)	0.029 (2)	0.0355 (19)	0.0004 (16)	0.0169 (15)	−0.0036 (17)
C5	0.0227 (17)	0.033 (2)	0.039 (2)	0.0037 (16)	0.0057 (15)	0.0045 (18)
C6	0.0254 (17)	0.034 (2)	0.0289 (18)	−0.0038 (16)	0.0022 (15)	0.0032 (17)
C7	0.0180 (15)	0.0166 (18)	0.0217 (16)	0.0020 (13)	0.0037 (13)	0.0001 (14)
C8	0.0185 (15)	0.0191 (18)	0.0176 (15)	0.0009 (13)	0.0066 (13)	0.0010 (13)
C9	0.0248 (15)	0.0193 (19)	0.0221 (15)	−0.0017 (14)	0.0063 (12)	−0.0032 (15)
C10	0.0291 (18)	0.025 (2)	0.0348 (19)	−0.0047 (15)	0.0175 (15)	−0.0048 (16)
C11	0.0272 (18)	0.023 (2)	0.0296 (19)	−0.0005 (15)	0.0042 (15)	−0.0018 (16)
C12	0.0252 (16)	0.027 (2)	0.0249 (17)	−0.0017 (15)	0.0098 (14)	−0.0024 (15)
C13	0.0212 (16)	0.0188 (19)	0.0308 (18)	−0.0029 (14)	0.0091 (14)	−0.0026 (14)
C14	0.0219 (16)	0.0178 (17)	0.0307 (18)	−0.0031 (14)	0.0132 (14)	−0.0008 (15)
C15	0.0252 (17)	0.026 (2)	0.0315 (18)	−0.0002 (15)	0.0122 (15)	0.0014 (16)
C16	0.0263 (18)	0.032 (2)	0.0299 (19)	−0.0056 (16)	0.0104 (15)	−0.0006 (16)
C17	0.0345 (19)	0.032 (2)	0.038 (2)	−0.0106 (17)	0.0241 (17)	−0.0103 (17)
C18	0.0280 (18)	0.0231 (19)	0.052 (2)	0.0039 (16)	0.0233 (17)	0.0039 (18)
C19	0.0279 (17)	0.026 (2)	0.0324 (18)	−0.0028 (16)	0.0156 (14)	0.0031 (16)
O1W	0.0281 (13)	0.0268 (16)	0.0327 (13)	−0.0001 (11)	0.0033 (10)	−0.0008 (11)

S1—C3	1.759 (3)	C9—C11	1.521 (5)
S1—C2	1.809 (3)	C9—C12	1.526 (5)
O1—C1	1.428 (3)	C10—H10A	0.9800
O1—H1O	0.833 (10)	C10—H10B	0.9800
O2—C8	1.219 (4)	C10—H10C	0.9800
O3—C8	1.357 (4)	C11—H11A	0.9800
O3—C9	1.473 (4)	C11—H11B	0.9800
N1—C4	1.343 (4)	C11—H11C	0.9800
N1—C3	1.345 (4)	C12—H12A	0.9800
N2—C3	1.321 (4)	C12—H12B	0.9800
N2—C6	1.349 (5)	C12—H12C	0.9800
N3—C8	1.350 (4)	C13—C14	1.513 (5)
N3—C7	1.458 (4)	C13—H13A	0.9900
N3—H3N	0.856 (10)	C13—H13B	0.9900
C1—C2	1.521 (4)	C14—C15	1.389 (5)
C1—C7	1.533 (4)	C14—C19	1.390 (5)
C1—H1	1.0000	C15—C16	1.383 (5)
C2—H2A	0.9900	C15—H15	0.9500
C2—H2B	0.9900	C16—C17	1.373 (5)
C4—C5	1.373 (5)	C16—H16	0.9500
C4—H4	0.9500	C17—C18	1.381 (5)
C5—C6	1.371 (5)	C17—H17	0.9500
C5—H5	0.9500	C18—C19	1.387 (5)
C6—H6	0.9500	C18—H18	0.9500
C7—C13	1.534 (4)	C19—H19	0.9500
C7—H7	1.0000	O1W—H1W	0.846 (10)
C9—C10	1.520 (5)	O1W—H2W	0.842 (10)
C3—S1—C2	102.08 (16)	C10—C9—C12	113.2 (3)
C1—O1—H1O	107 (3)	C11—C9—C12	109.8 (3)
C8—O3—C9	120.2 (2)	C9—C10—H10A	109.5
C4—N1—C3	115.3 (3)	C9—C10—H10B	109.5
C3—N2—C6	114.9 (3)	H10A—C10—H10B	109.5
C8—N3—C7	122.1 (3)	C9—C10—H10C	109.5
C8—N3—H3N	117 (2)	H10A—C10—H10C	109.5
C7—N3—H3N	118 (2)	H10B—C10—H10C	109.5
O1—C1—C2	108.3 (2)	C9—C11—H11A	109.5
O1—C1—C7	107.9 (2)	C9—C11—H11B	109.5
C2—C1—C7	111.3 (3)	H11A—C11—H11B	109.5
O1—C1—H1	109.8	C9—C11—H11C	109.5
C2—C1—H1	109.8	H11A—C11—H11C	109.5
C7—C1—H1	109.8	H11B—C11—H11C	109.5
C1—C2—S1	112.5 (2)	C9—C12—H12A	109.5
C1—C2—H2A	109.1	C9—C12—H12B	109.5
S1—C2—H2A	109.1	H12A—C12—H12B	109.5
C1—C2—H2B	109.1	C9—C12—H12C	109.5
S1—C2—H2B	109.1	H12A—C12—H12C	109.5
H2A—C2—H2B	107.8	H12B—C12—H12C	109.5
N2—C3—N1	127.6 (3)	C14—C13—C7	112.4 (3)
N2—C3—S1	120.6 (3)	C14—C13—H13A	109.1
N1—C3—S1	111.8 (2)	C7—C13—H13A	109.1
N1—C4—C5	122.4 (3)	C14—C13—H13B	109.1
N1—C4—H4	118.8	C7—C13—H13B	109.1
C5—C4—H4	118.8	H13A—C13—H13B	107.9
C6—C5—C4	116.9 (3)	C15—C14—C19	118.5 (3)
C6—C5—H5	121.5	C15—C14—C13	121.7 (3)
C4—C5—H5	121.5	C19—C14—C13	119.7 (3)
N2—C6—C5	123.0 (3)	C16—C15—C14	120.6 (3)
N2—C6—H6	118.5	C16—C15—H15	119.7
C5—C6—H6	118.5	C14—C15—H15	119.7
N3—C7—C1	109.9 (2)	C17—C16—C15	120.4 (3)
N3—C7—C13	109.6 (2)	C17—C16—H16	119.8
C1—C7—C13	111.4 (3)	C15—C16—H16	119.8
N3—C7—H7	108.6	C16—C17—C18	119.9 (3)
C1—C7—H7	108.6	C16—C17—H17	120.0
C13—C7—H7	108.6	C18—C17—H17	120.0
O2—C8—N3	125.5 (3)	C17—C18—C19	119.8 (3)
O2—C8—O3	125.3 (3)	C17—C18—H18	120.1
N3—C8—O3	109.3 (3)	C19—C18—H18	120.1
O3—C9—C10	109.6 (2)	C18—C19—C14	120.8 (3)
O3—C9—C11	102.2 (3)	C18—C19—H19	119.6
C10—C9—C11	110.7 (3)	C14—C19—H19	119.6
O3—C9—C12	110.9 (2)	H1W—O1W—H2W	107 (4)
O1—C1—C2—S1	65.2 (3)	C7—N3—C8—O2	15.8 (5)
C7—C1—C2—S1	−176.4 (2)	C7—N3—C8—O3	−165.2 (3)
C3—S1—C2—C1	89.9 (2)	C9—O3—C8—O2	−3.5 (5)
C6—N2—C3—N1	1.4 (5)	C9—O3—C8—N3	177.5 (2)
C6—N2—C3—S1	−179.2 (3)	C8—O3—C9—C10	70.1 (3)
C4—N1—C3—N2	−0.6 (5)	C8—O3—C9—C11	−172.5 (3)
C4—N1—C3—S1	179.9 (2)	C8—O3—C9—C12	−55.5 (4)
C2—S1—C3—N2	−0.9 (3)	N3—C7—C13—C14	−70.4 (3)
C2—S1—C3—N1	178.6 (2)	C1—C7—C13—C14	167.8 (3)
C3—N1—C4—C5	0.1 (5)	C7—C13—C14—C15	91.7 (4)
N1—C4—C5—C6	−0.5 (5)	C7—C13—C14—C19	−86.0 (4)
C3—N2—C6—C5	−1.7 (5)	C19—C14—C15—C16	1.2 (5)
C4—C5—C6—N2	1.4 (6)	C13—C14—C15—C16	−176.5 (3)
C8—N3—C7—C1	−135.6 (3)	C14—C15—C16—C17	−0.7 (5)
C8—N3—C7—C13	101.7 (3)	C15—C16—C17—C18	−0.5 (5)
O1—C1—C7—N3	−179.3 (3)	C16—C17—C18—C19	1.1 (5)
C2—C1—C7—N3	62.0 (3)	C17—C18—C19—C14	−0.6 (5)
O1—C1—C7—C13	−57.7 (3)	C15—C14—C19—C18	−0.5 (5)
C2—C1—C7—C13	−176.3 (3)	C13—C14—C19—C18	177.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O1wi	0.83 (2)	2.00 (2)	2.813 (4)	168 (4)
O1w—H1w···N1ii	0.85 (2)	2.12 (2)	2.958 (4)	174 (4)
O1w—H2w···O1	0.84 (3)	2.06 (3)	2.893 (4)	170 (4)
N3—H3n···O2i	0.859 (19)	2.126 (16)	2.910 (3)	152 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯O1wi	0.83 (2)	2.00 (2)	2.813 (4)	168 (4)
O1w—H1w⋯N1ii	0.85 (2)	2.12 (2)	2.958 (4)	174 (4)
O1w—H2w⋯O1	0.84 (3)	2.06 (3)	2.893 (4)	170 (4)
N3—H3n⋯O2i	0.86 (2)	2.13 (2)	2.910 (3)	152 (3)

Symmetry codes: (i) ; (ii) .