Methyl 2-(2-{[(benz-yloxy)carbon-yl]amino}-propan-2-yl)-5-hy-droxy-6-meth-oxy-pyrimidine-4-carboxyl-ate.

In the title compound, C(18)H(21)N(3)O(6), the dihedral angle between the two aromatic rings is 61.1 (1)°. The crystal structure is stabilized by inter-molecular O-H⋯O hydrogen bonds. An intra-molecular O-H⋯O hydrogen bonds is also present.

Related literature

The title compound was obtained in an attempt to synthesise an inter­mediate for the anti­retroviral drug raltegravir [sys­tem­atic name N-(2-(4-(4-fluoro­benzyl­carbamo­yl)-5-hy­droxy-1-methyl-6-oxo-1,6-dihydro­pyrimidin-2-yl)propan-2-yl)-5-methyl-1,3,4-oxadiazole-2-carboxamide], see: Belyk et al. (2006) ▶. For background to raltegravir, see: Steigbigel et al. (2008 ▶). For related structures, see: Shang & Shang (2007 ▶); Fun et al. (2009 ▶).

Experimental

Crystal data

C18H21N3O6

M = 375.38

Monoclinic,

a = 8.5313 (17) Å

b = 6.5413 (13) Å

c = 16.167 (3) Å

β = 97.37 (3)°

V = 894.7 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 113 K

0.20 × 0.16 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.979, T max = 0.987

7509 measured reflections

2281 independent reflections

1854 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.088

S = 1.01

2281 reflections

256 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681101628X/hg5023sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681101628X/hg5023Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681101628X/hg5023Isup3.cml

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

C18H21N3O6	F(000) = 396
Mr = 375.38	Dx = 1.393 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3543 reflections
a = 8.5313 (17) Å	θ = 2.3–27.5°
b = 6.5413 (13) Å	µ = 0.11 mm−1
c = 16.167 (3) Å	T = 113 K
β = 97.37 (3)°	Plate, colorless
V = 894.7 (3) Å3	0.20 × 0.16 × 0.12 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	2281 independent reflections
Radiation source: rotating anode	1854 reflections with I > 2σ(I)
confocal	Rint = 0.044
Detector resolution: 7.31 pixels mm-1	θmax = 27.9°, θmin = 2.5°
ω and φ scans	h = −10→11
Absorption correction: multi-scan (SADABS; Bruker, 1997)	k = −7→8
Tmin = 0.979, Tmax = 0.987	l = −21→20
7509 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0491P)2] where P = (Fo2 + 2Fc2)/3
2281 reflections	(Δ/σ)max = 0.001
256 parameters	Δρmax = 0.25 e Å−3
1 restraint	Δρmin = −0.21 e Å−3

Experimental. 1H-NMR (500 MHz, CDCl3) 1.72(s, 6H), 3.66(s, 3H), 3.97(s, 3H), 5.03(s, 2H), 5.28 (s, 1H), 7.02–7.32(m, 5H, J=75 Hz), 10.39(s, 1H).

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.

	x	y	z	Uiso*/Ueq
N1	0.7129 (2)	0.6028 (3)	0.89047 (10)	0.0184 (4)
N2	0.4395 (2)	0.6250 (3)	0.83861 (10)	0.0192 (4)
N3	0.4877 (2)	0.4973 (3)	0.68708 (11)	0.0210 (4)
H3	0.427 (3)	0.599 (5)	0.6595 (17)	0.043 (8)*
O1	0.25348 (16)	0.6638 (3)	0.92818 (9)	0.0220 (4)
O2	0.46916 (18)	0.6583 (3)	1.06058 (9)	0.0219 (4)
H2	0.547 (3)	0.670 (6)	1.1011 (18)	0.050 (9)*
O3	0.77719 (17)	0.6582 (3)	1.11167 (8)	0.0244 (4)
O4	0.94697 (16)	0.6036 (3)	1.01878 (9)	0.0231 (4)
O5	0.4667 (2)	0.2009 (2)	0.76039 (9)	0.0259 (4)
O6	0.26425 (19)	0.3210 (3)	0.66809 (10)	0.0287 (4)
C1	0.5941 (2)	0.6005 (3)	0.82953 (12)	0.0185 (5)
C2	0.4043 (2)	0.6444 (3)	0.91420 (12)	0.0183 (4)
C3	0.5207 (2)	0.6435 (3)	0.98553 (12)	0.0174 (4)
C4	0.6744 (2)	0.6263 (3)	0.96913 (12)	0.0174 (4)
C5	0.1359 (2)	0.6528 (4)	0.85502 (12)	0.0240 (5)
H5A	0.1437	0.7746	0.8205	0.036*
H5B	0.0302	0.6460	0.8725	0.036*
H5C	0.1544	0.5304	0.8227	0.036*
C6	0.8042 (2)	0.6304 (4)	1.04017 (12)	0.0193 (4)
C7	1.0779 (3)	0.6187 (4)	1.08615 (13)	0.0258 (5)
H7A	1.0933	0.7620	1.1029	0.039*
H7B	1.1745	0.5663	1.0669	0.039*
H7C	1.0537	0.5379	1.1340	0.039*
C8	0.6296 (3)	0.5754 (3)	0.73967 (13)	0.0197 (5)
C9	0.7695 (3)	0.4322 (4)	0.73342 (14)	0.0261 (6)
H9A	0.7435	0.2947	0.7515	0.039*
H9B	0.8627	0.4831	0.7693	0.039*
H9C	0.7920	0.4271	0.6755	0.039*
C10	0.6641 (3)	0.7866 (4)	0.70588 (15)	0.0285 (6)
H10A	0.6796	0.7750	0.6470	0.043*
H10B	0.7600	0.8422	0.7378	0.043*
H10C	0.5749	0.8780	0.7111	0.043*
C11	0.4121 (3)	0.3289 (4)	0.71076 (12)	0.0211 (5)
C12	0.1749 (3)	0.1388 (4)	0.67933 (14)	0.0313 (6)
H12A	0.0616	0.1746	0.6762	0.038*
H12B	0.2092	0.0820	0.7355	0.038*
C13	0.1953 (3)	−0.0221 (4)	0.61451 (14)	0.0248 (5)
C14	0.3061 (3)	−0.0041 (5)	0.55949 (14)	0.0322 (6)
H14	0.3742	0.1112	0.5625	0.039*
C15	0.3181 (3)	−0.1545 (5)	0.49977 (15)	0.0399 (7)
H15	0.3942	−0.1411	0.4621	0.048*
C16	0.2197 (4)	−0.3238 (5)	0.49494 (16)	0.0427 (7)
H16	0.2290	−0.4268	0.4544	0.051*
C17	0.1087 (3)	−0.3423 (5)	0.54905 (15)	0.0379 (7)
H17	0.0401	−0.4572	0.5455	0.046*
C18	0.0970 (3)	−0.1928 (4)	0.60889 (14)	0.0293 (6)
H18	0.0209	−0.2072	0.6465	0.035*

	U11	U22	U33	U12	U13	U23
N1	0.0175 (9)	0.0203 (10)	0.0177 (8)	0.0002 (8)	0.0028 (7)	−0.0018 (7)
N2	0.0165 (9)	0.0218 (9)	0.0190 (8)	0.0010 (8)	0.0020 (7)	−0.0023 (8)
N3	0.0206 (10)	0.0237 (10)	0.0178 (9)	0.0015 (8)	−0.0011 (7)	0.0003 (8)
O1	0.0129 (8)	0.0321 (9)	0.0211 (7)	0.0017 (7)	0.0021 (6)	−0.0023 (7)
O2	0.0196 (8)	0.0282 (9)	0.0176 (7)	0.0007 (7)	0.0020 (6)	−0.0022 (7)
O3	0.0215 (8)	0.0348 (10)	0.0170 (7)	0.0017 (8)	0.0035 (6)	−0.0023 (7)
O4	0.0126 (8)	0.0357 (10)	0.0209 (7)	−0.0004 (7)	0.0014 (6)	−0.0023 (7)
O5	0.0303 (10)	0.0250 (9)	0.0225 (8)	0.0032 (7)	0.0037 (7)	0.0021 (7)
O6	0.0249 (9)	0.0295 (9)	0.0295 (8)	−0.0040 (8)	−0.0044 (7)	−0.0018 (7)
C1	0.0180 (11)	0.0182 (11)	0.0193 (10)	0.0003 (9)	0.0024 (8)	−0.0012 (8)
C2	0.0161 (11)	0.0153 (11)	0.0236 (10)	0.0004 (9)	0.0032 (8)	−0.0011 (9)
C3	0.0208 (11)	0.0141 (10)	0.0174 (9)	−0.0015 (9)	0.0026 (8)	−0.0019 (8)
C4	0.0174 (11)	0.0164 (10)	0.0182 (9)	−0.0007 (9)	0.0017 (8)	−0.0012 (8)
C5	0.0176 (11)	0.0316 (13)	0.0214 (11)	0.0008 (10)	−0.0028 (8)	−0.0020 (10)
C6	0.0200 (11)	0.0191 (11)	0.0184 (10)	−0.0026 (10)	0.0009 (8)	−0.0002 (9)
C7	0.0190 (12)	0.0376 (14)	0.0196 (10)	−0.0044 (11)	−0.0016 (9)	0.0005 (10)
C8	0.0168 (11)	0.0253 (12)	0.0169 (10)	0.0001 (9)	0.0010 (8)	−0.0015 (8)
C9	0.0196 (13)	0.0385 (14)	0.0199 (11)	0.0036 (10)	0.0012 (9)	−0.0043 (10)
C10	0.0291 (14)	0.0307 (13)	0.0266 (12)	−0.0061 (11)	0.0073 (10)	0.0002 (10)
C11	0.0222 (12)	0.0257 (12)	0.0157 (10)	0.0002 (10)	0.0037 (9)	−0.0054 (9)
C12	0.0270 (13)	0.0359 (15)	0.0317 (12)	−0.0110 (12)	0.0068 (10)	−0.0065 (12)
C13	0.0214 (12)	0.0316 (13)	0.0204 (10)	−0.0016 (10)	−0.0009 (9)	0.0004 (9)
C14	0.0267 (14)	0.0426 (16)	0.0269 (12)	−0.0030 (12)	0.0021 (10)	−0.0024 (11)
C15	0.0376 (16)	0.056 (2)	0.0256 (12)	0.0101 (15)	0.0042 (11)	−0.0030 (13)
C16	0.0589 (19)	0.0398 (17)	0.0267 (13)	0.0142 (15)	−0.0054 (13)	−0.0064 (12)
C17	0.0522 (17)	0.0255 (13)	0.0324 (13)	−0.0012 (13)	−0.0088 (12)	0.0023 (11)
C18	0.0325 (14)	0.0309 (14)	0.0231 (11)	−0.0050 (11)	−0.0020 (10)	0.0032 (10)

N1—C1	1.320 (2)	C7—H7B	0.9800
N1—C4	1.363 (3)	C7—H7C	0.9800
N2—C2	1.301 (3)	C8—C10	1.528 (3)
N2—C1	1.355 (3)	C8—C9	1.531 (3)
N3—C11	1.357 (3)	C9—H9A	0.9800
N3—C8	1.478 (3)	C9—H9B	0.9800
N3—H3	0.92 (3)	C9—H9C	0.9800
O1—C2	1.341 (2)	C10—H10A	0.9800
O1—C5	1.451 (2)	C10—H10B	0.9800
O2—C3	1.346 (3)	C10—H10C	0.9800
O2—H2	0.87 (3)	C12—C13	1.511 (3)
O3—C6	1.221 (2)	C12—H12A	0.9900
O4—C6	1.320 (3)	C12—H12B	0.9900
O4—C7	1.460 (2)	C13—C14	1.384 (3)
O5—C11	1.211 (3)	C13—C18	1.392 (4)
O6—C11	1.358 (3)	C14—C15	1.391 (4)
O6—C12	1.438 (3)	C14—H14	0.9500
C1—C8	1.530 (3)	C15—C16	1.386 (5)
C2—C3	1.422 (3)	C15—H15	0.9500
C3—C4	1.375 (3)	C16—C17	1.375 (4)
C4—C6	1.490 (3)	C16—H16	0.9500
C5—H5A	0.9800	C17—C18	1.388 (4)
C5—H5B	0.9800	C17—H17	0.9500
C5—H5C	0.9800	C18—H18	0.9500
C7—H7A	0.9800
C1—N1—C4	116.32 (18)	C1—C8—C9	112.28 (18)
C2—N2—C1	117.25 (17)	C8—C9—H9A	109.5
C11—N3—C8	120.17 (17)	C8—C9—H9B	109.5
C11—N3—H3	117.4 (18)	H9A—C9—H9B	109.5
C8—N3—H3	113.6 (19)	C8—C9—H9C	109.5
C2—O1—C5	115.85 (16)	H9A—C9—H9C	109.5
C3—O2—H2	112 (2)	H9B—C9—H9C	109.5
C6—O4—C7	116.03 (16)	C8—C10—H10A	109.5
C11—O6—C12	116.08 (19)	C8—C10—H10B	109.5
N1—C1—N2	125.66 (19)	H10A—C10—H10B	109.5
N1—C1—C8	118.88 (18)	C8—C10—H10C	109.5
N2—C1—C8	115.42 (17)	H10A—C10—H10C	109.5
N2—C2—O1	120.61 (17)	H10B—C10—H10C	109.5
N2—C2—C3	122.69 (19)	O5—C11—N3	126.3 (2)
O1—C2—C3	116.69 (18)	O5—C11—O6	124.3 (2)
O2—C3—C4	127.57 (18)	N3—C11—O6	109.39 (18)
O2—C3—C2	117.10 (18)	O6—C12—C13	112.31 (19)
C4—C3—C2	115.33 (18)	O6—C12—H12A	109.1
N1—C4—C3	122.66 (17)	C13—C12—H12A	109.1
N1—C4—C6	118.47 (18)	O6—C12—H12B	109.1
C3—C4—C6	118.86 (18)	C13—C12—H12B	109.1
O1—C5—H5A	109.5	H12A—C12—H12B	107.9
O1—C5—H5B	109.5	C14—C13—C18	118.8 (2)
H5A—C5—H5B	109.5	C14—C13—C12	122.4 (2)
O1—C5—H5C	109.5	C18—C13—C12	118.8 (2)
H5A—C5—H5C	109.5	C13—C14—C15	120.2 (3)
H5B—C5—H5C	109.5	C13—C14—H14	119.9
O3—C6—O4	124.10 (18)	C15—C14—H14	119.9
O3—C6—C4	121.35 (19)	C16—C15—C14	120.4 (3)
O4—C6—C4	114.55 (17)	C16—C15—H15	119.8
O4—C7—H7A	109.5	C14—C15—H15	119.8
O4—C7—H7B	109.5	C17—C16—C15	119.7 (3)
H7A—C7—H7B	109.5	C17—C16—H16	120.1
O4—C7—H7C	109.5	C15—C16—H16	120.1
H7A—C7—H7C	109.5	C16—C17—C18	119.9 (3)
H7B—C7—H7C	109.5	C16—C17—H17	120.0
N3—C8—C10	106.74 (17)	C18—C17—H17	120.0
N3—C8—C1	109.65 (18)	C17—C18—C13	120.9 (3)
C10—C8—C1	108.25 (18)	C17—C18—H18	119.5
N3—C8—C9	109.79 (19)	C13—C18—H18	119.5
C10—C8—C9	110.0 (2)
C4—N1—C1—N2	2.0 (3)	C11—N3—C8—C10	−168.3 (2)
C4—N1—C1—C8	179.8 (2)	C11—N3—C8—C1	−51.3 (3)
C2—N2—C1—N1	−2.9 (3)	C11—N3—C8—C9	72.5 (3)
C2—N2—C1—C8	179.2 (2)	N1—C1—C8—N3	158.04 (19)
C1—N2—C2—O1	−178.2 (2)	N2—C1—C8—N3	−23.9 (3)
C1—N2—C2—C3	0.9 (3)	N1—C1—C8—C10	−85.9 (2)
C5—O1—C2—N2	2.5 (3)	N2—C1—C8—C10	92.1 (2)
C5—O1—C2—C3	−176.63 (19)	N1—C1—C8—C9	35.7 (3)
N2—C2—C3—O2	−177.9 (2)	N2—C1—C8—C9	−146.3 (2)
O1—C2—C3—O2	1.2 (3)	C8—N3—C11—O5	−19.5 (3)
N2—C2—C3—C4	1.7 (3)	C8—N3—C11—O6	162.23 (18)
O1—C2—C3—C4	−179.13 (19)	C12—O6—C11—O5	−5.0 (3)
C1—N1—C4—C3	1.0 (3)	C12—O6—C11—N3	173.27 (18)
C1—N1—C4—C6	−179.9 (2)	C11—O6—C12—C13	−92.1 (2)
O2—C3—C4—N1	176.9 (2)	O6—C12—C13—C14	9.1 (3)
C2—C3—C4—N1	−2.7 (3)	O6—C12—C13—C18	−169.70 (19)
O2—C3—C4—C6	−2.2 (3)	C18—C13—C14—C15	0.1 (3)
C2—C3—C4—C6	178.2 (2)	C12—C13—C14—C15	−178.7 (2)
C7—O4—C6—O3	−2.9 (3)	C13—C14—C15—C16	−0.2 (4)
C7—O4—C6—C4	176.54 (19)	C14—C15—C16—C17	0.6 (4)
N1—C4—C6—O3	177.4 (2)	C15—C16—C17—C18	−0.8 (4)
C3—C4—C6—O3	−3.5 (3)	C16—C17—C18—C13	0.7 (4)
N1—C4—C6—O4	−2.1 (3)	C14—C13—C18—C17	−0.4 (3)
C3—C4—C6—O4	177.1 (2)	C12—C13—C18—C17	178.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O5i	0.87 (3)	2.27 (3)	2.889 (2)	128 (2)
O2—H2···O3	0.87 (3)	1.95 (3)	2.652 (2)	136 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O5i	0.87 (3)	2.27 (3)	2.889 (2)	128 (2)
O2—H2⋯O3	0.87 (3)	1.95 (3)	2.652 (2)	136 (3)

Symmetry code: (i) .