Methyl 2-(2-{[(benz-yloxy)carbon-yl]amino}-propan-2-yl)-5-hy-droxy-6-oxo-1,6-dihydro-pyrimidine-4-carboxyl-ate.

In the title compound, C(17)H(19)N(3)O(6), the dihedral angle between the two aromatic rings is 45.9 (1)°. The crystal structure is stabilized through inter-molecular N-H⋯O hydrogen bonds and intra-molecular O-H⋯O hydrogen bonds are also present.

Related literature

For related structures, see: Fun et al. (2009 ▶); Shang & Shang (2007 ▶). The title compound is an inter­mediate in the preparation of 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. For therapeutic details of raltegravir, see Steigbigel et al. (2008 ▶). For synthetic details, see: Culbertson (1979 ▶).

Experimental

Crystal data

C17H19N3O6

M = 361.35

Monoclinic,

a = 12.122 (2) Å

b = 16.300 (3) Å

c = 9.1766 (18) Å

β = 106.29 (3)°

V = 1740.4 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 113 K

0.24 × 0.20 × 0.16 mm

Data collection

Bruker SMART diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.975, T max = 0.983

15564 measured reflections

4142 independent reflections

3386 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.103

S = 1.09

4142 reflections

250 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.24 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/S1600536811016278/wn2426sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016278/wn2426Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811016278/wn2426Isup3.cml

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

C17H19N3O6	Dx = 1.379 Mg m−3
Mr = 361.35	Melting point = 183–185 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.122 (2) Å	Cell parameters from 4990 reflections
b = 16.300 (3) Å	θ = 2.5–27.9°
c = 9.1766 (18) Å	µ = 0.11 mm−1
β = 106.29 (3)°	T = 113 K
V = 1740.4 (6) Å3	Plate, colorless
Z = 4	0.24 × 0.20 × 0.16 mm
F(000) = 760

Bruker SMART diffractometer	4142 independent reflections
Radiation source: rotating anode	3386 reflections with I > 2σ(I)
confocal	Rint = 0.035
ω scans	θmax = 27.9°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −15→15
Tmin = 0.975, Tmax = 0.983	k = −21→18
15564 measured reflections	l = −11→12

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) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0539P)2 + 0.1964P] where P = (Fo2 + 2Fc2)/3
4142 reflections	(Δ/σ)max = 0.001
250 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Experimental. 1H-NMR (500 MHz, DMSO) 1.51(s, 6H), 3.82(s, 3H), 4.98(s, 2H), 7.35(bs, 5H), 7.45 (s, 1H), 10.24(s, 1H), 12.58(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	0.18567 (8)	0.11941 (5)	0.81459 (10)	0.0159 (2)
N2	0.36822 (8)	0.06461 (6)	0.92786 (11)	0.0179 (2)
N3	0.39582 (8)	0.18366 (6)	1.15086 (11)	0.0170 (2)
O1	0.28432 (8)	−0.00917 (5)	0.54614 (9)	0.0247 (2)
O2	0.45987 (7)	−0.02265 (5)	0.80609 (9)	0.0282 (2)
O3	0.08230 (7)	0.05655 (5)	0.42611 (9)	0.0234 (2)
O4	0.01176 (7)	0.14406 (5)	0.56692 (9)	0.01951 (19)
O5	0.40819 (7)	0.26902 (6)	0.95868 (9)	0.0279 (2)
O6	0.54363 (7)	0.26725 (5)	1.18631 (10)	0.0285 (2)
C1	0.27523 (9)	0.11186 (6)	0.93025 (12)	0.0148 (2)
C2	0.18776 (9)	0.07855 (6)	0.68378 (12)	0.0160 (2)
C3	0.27744 (10)	0.03116 (7)	0.67123 (12)	0.0176 (2)
C4	0.37656 (10)	0.02098 (7)	0.80389 (13)	0.0196 (2)
C5	0.27947 (9)	0.15246 (6)	1.08134 (12)	0.0157 (2)
C6	0.18968 (10)	0.22037 (7)	1.05981 (14)	0.0215 (3)
H6A	0.1929	0.2448	1.1585	0.032*
H6B	0.1130	0.1973	1.0147	0.032*
H6C	0.2055	0.2626	0.9924	0.032*
C7	0.25766 (11)	0.08712 (7)	1.18957 (13)	0.0216 (3)
H7A	0.3156	0.0437	1.2026	0.032*
H7B	0.1810	0.0635	1.1472	0.032*
H7C	0.2624	0.1122	1.2882	0.032*
C8	0.08872 (9)	0.09093 (7)	0.54685 (12)	0.0171 (2)
C9	−0.07754 (10)	0.16603 (8)	0.43090 (14)	0.0259 (3)
H9A	−0.0423	0.1845	0.3526	0.039*
H9B	−0.1245	0.2103	0.4542	0.039*
H9C	−0.1262	0.1181	0.3938	0.039*
C10	0.44448 (10)	0.24266 (7)	1.08715 (13)	0.0185 (2)
C11	0.60365 (11)	0.33419 (8)	1.13972 (14)	0.0266 (3)
H11A	0.5518	0.3818	1.1074	0.032*
H11B	0.6333	0.3173	1.0541	0.032*
C12	0.70133 (10)	0.35578 (7)	1.27658 (13)	0.0206 (3)
C13	0.68387 (11)	0.36043 (8)	1.41951 (14)	0.0247 (3)
H13	0.6100	0.3491	1.4314	0.030*
C14	0.77345 (11)	0.38150 (8)	1.54519 (15)	0.0284 (3)
H14	0.7609	0.3838	1.6427	0.034*
C15	0.88144 (11)	0.39923 (8)	1.52900 (16)	0.0302 (3)
H15	0.9424	0.4144	1.6149	0.036*
C16	0.89961 (11)	0.39465 (8)	1.38730 (16)	0.0282 (3)
H16	0.9733	0.4067	1.3755	0.034*
C17	0.80992 (10)	0.37236 (7)	1.26174 (15)	0.0230 (3)
H17	0.8232	0.3685	1.1648	0.028*
H3	0.4221 (12)	0.1800 (8)	1.2505 (17)	0.024 (3)*
H2	0.4269 (13)	0.0577 (9)	1.0186 (18)	0.036 (4)*
H1	0.2178 (15)	0.0049 (10)	0.474 (2)	0.045 (5)*

	U11	U22	U33	U12	U13	U23
N1	0.0170 (5)	0.0159 (4)	0.0139 (4)	−0.0015 (3)	0.0029 (4)	−0.0008 (3)
N2	0.0177 (5)	0.0210 (5)	0.0134 (4)	0.0034 (4)	0.0014 (4)	−0.0024 (4)
N3	0.0182 (5)	0.0189 (5)	0.0116 (4)	−0.0021 (4)	0.0004 (4)	−0.0005 (4)
O1	0.0292 (5)	0.0293 (5)	0.0143 (4)	0.0056 (4)	0.0038 (4)	−0.0051 (3)
O2	0.0265 (5)	0.0372 (5)	0.0188 (4)	0.0140 (4)	0.0029 (4)	−0.0049 (4)
O3	0.0259 (5)	0.0283 (4)	0.0135 (4)	−0.0018 (3)	0.0012 (3)	−0.0026 (3)
O4	0.0173 (4)	0.0220 (4)	0.0158 (4)	0.0007 (3)	−0.0010 (3)	0.0012 (3)
O5	0.0294 (5)	0.0371 (5)	0.0142 (4)	−0.0095 (4)	0.0009 (3)	0.0056 (4)
O6	0.0273 (5)	0.0334 (5)	0.0189 (4)	−0.0152 (4)	−0.0031 (4)	0.0055 (4)
C1	0.0154 (5)	0.0143 (5)	0.0147 (5)	−0.0011 (4)	0.0040 (4)	0.0004 (4)
C2	0.0180 (6)	0.0156 (5)	0.0129 (5)	−0.0018 (4)	0.0019 (4)	0.0005 (4)
C3	0.0227 (6)	0.0164 (5)	0.0130 (5)	−0.0011 (4)	0.0037 (4)	−0.0015 (4)
C4	0.0220 (6)	0.0202 (6)	0.0158 (5)	0.0029 (4)	0.0040 (4)	−0.0011 (4)
C5	0.0158 (5)	0.0169 (5)	0.0135 (5)	−0.0011 (4)	0.0025 (4)	−0.0028 (4)
C6	0.0209 (6)	0.0212 (6)	0.0209 (6)	0.0033 (4)	0.0034 (5)	−0.0051 (5)
C7	0.0265 (6)	0.0216 (6)	0.0182 (6)	−0.0037 (4)	0.0087 (5)	−0.0015 (4)
C8	0.0183 (6)	0.0171 (5)	0.0149 (5)	−0.0043 (4)	0.0031 (4)	0.0009 (4)
C9	0.0209 (6)	0.0308 (7)	0.0201 (6)	0.0011 (5)	−0.0037 (5)	0.0048 (5)
C10	0.0197 (6)	0.0209 (5)	0.0139 (5)	−0.0017 (4)	0.0030 (4)	−0.0018 (4)
C11	0.0276 (7)	0.0319 (7)	0.0181 (6)	−0.0124 (5)	0.0028 (5)	0.0028 (5)
C12	0.0208 (6)	0.0190 (5)	0.0204 (6)	−0.0025 (4)	0.0034 (5)	0.0002 (4)
C13	0.0195 (6)	0.0305 (6)	0.0230 (6)	−0.0005 (5)	0.0041 (5)	−0.0011 (5)
C14	0.0306 (7)	0.0309 (7)	0.0206 (6)	0.0027 (5)	0.0020 (5)	−0.0040 (5)
C15	0.0239 (6)	0.0263 (6)	0.0317 (7)	−0.0014 (5)	−0.0067 (5)	0.0005 (5)
C16	0.0172 (6)	0.0249 (6)	0.0390 (7)	−0.0007 (5)	0.0019 (5)	0.0080 (6)
C17	0.0236 (6)	0.0202 (6)	0.0262 (6)	0.0016 (4)	0.0084 (5)	0.0042 (5)

N1—C1	1.2937 (14)	C6—H6A	0.9800
N1—C2	1.3792 (14)	C6—H6B	0.9800
N2—C4	1.3692 (15)	C6—H6C	0.9800
N2—C1	1.3704 (14)	C7—H7A	0.9800
N2—H2	0.938 (16)	C7—H7B	0.9800
N3—C10	1.3446 (15)	C7—H7C	0.9800
N3—C5	1.4663 (14)	C9—H9A	0.9800
N3—H3	0.882 (15)	C9—H9B	0.9800
O1—C3	1.3456 (14)	C9—H9C	0.9800
O1—H1	0.918 (17)	C11—C12	1.5062 (16)
O2—C4	1.2308 (14)	C11—H11A	0.9900
O3—C8	1.2245 (14)	C11—H11B	0.9900
O4—C8	1.3230 (14)	C12—C17	1.3874 (18)
O4—C9	1.4491 (13)	C12—C13	1.3881 (18)
O5—C10	1.2154 (14)	C13—C14	1.3872 (17)
O6—C10	1.3489 (13)	C13—H13	0.9500
O6—C11	1.4413 (14)	C14—C15	1.389 (2)
C1—C5	1.5242 (15)	C14—H14	0.9500
C2—C3	1.3646 (16)	C15—C16	1.380 (2)
C2—C8	1.4881 (15)	C15—H15	0.9500
C3—C4	1.4602 (16)	C16—C17	1.3924 (18)
C5—C6	1.5259 (15)	C16—H16	0.9500
C5—C7	1.5291 (16)	C17—H17	0.9500
C1—N1—C2	116.87 (10)	H7A—C7—H7C	109.5
C4—N2—C1	123.91 (10)	H7B—C7—H7C	109.5
C4—N2—H2	117.4 (9)	O3—C8—O4	123.86 (10)
C1—N2—H2	118.4 (9)	O3—C8—C2	122.24 (11)
C10—N3—C5	123.00 (9)	O4—C8—C2	113.87 (9)
C10—N3—H3	115.1 (9)	O4—C9—H9A	109.5
C5—N3—H3	116.8 (9)	O4—C9—H9B	109.5
C3—O1—H1	104.1 (11)	H9A—C9—H9B	109.5
C8—O4—C9	115.30 (9)	O4—C9—H9C	109.5
C10—O6—C11	116.95 (9)	H9A—C9—H9C	109.5
N1—C1—N2	123.03 (10)	H9B—C9—H9C	109.5
N1—C1—C5	120.75 (10)	O5—C10—N3	126.23 (11)
N2—C1—C5	116.14 (9)	O5—C10—O6	124.12 (11)
C3—C2—N1	123.81 (10)	N3—C10—O6	109.62 (9)
C3—C2—C8	118.60 (10)	O6—C11—C12	105.89 (9)
N1—C2—C8	117.51 (10)	O6—C11—H11A	110.6
O1—C3—C2	126.16 (10)	C12—C11—H11A	110.6
O1—C3—C4	114.98 (10)	O6—C11—H11B	110.6
C2—C3—C4	118.86 (10)	C12—C11—H11B	110.6
O2—C4—N2	122.55 (10)	H11A—C11—H11B	108.7
O2—C4—C3	123.97 (11)	C17—C12—C13	118.85 (11)
N2—C4—C3	113.48 (10)	C17—C12—C11	120.61 (12)
N3—C5—C1	109.22 (9)	C13—C12—C11	120.53 (11)
N3—C5—C6	111.64 (9)	C14—C13—C12	120.51 (12)
C1—C5—C6	110.88 (9)	C14—C13—H13	119.7
N3—C5—C7	106.23 (9)	C12—C13—H13	119.7
C1—C5—C7	108.70 (9)	C13—C14—C15	120.27 (13)
C6—C5—C7	110.02 (10)	C13—C14—H14	119.9
C5—C6—H6A	109.5	C15—C14—H14	119.9
C5—C6—H6B	109.5	C16—C15—C14	119.59 (12)
H6A—C6—H6B	109.5	C16—C15—H15	120.2
C5—C6—H6C	109.5	C14—C15—H15	120.2
H6A—C6—H6C	109.5	C15—C16—C17	119.98 (12)
H6B—C6—H6C	109.5	C15—C16—H16	120.0
C5—C7—H7A	109.5	C17—C16—H16	120.0
C5—C7—H7B	109.5	C12—C17—C16	120.77 (13)
H7A—C7—H7B	109.5	C12—C17—H17	119.6
C5—C7—H7C	109.5	C16—C17—H17	119.6
C2—N1—C1—N2	−1.36 (16)	N1—C1—C5—C7	102.55 (12)
C2—N1—C1—C5	−178.04 (9)	N2—C1—C5—C7	−74.35 (12)
C4—N2—C1—N1	0.28 (18)	C9—O4—C8—O3	−5.78 (16)
C4—N2—C1—C5	177.10 (10)	C9—O4—C8—C2	171.97 (9)
C1—N1—C2—C3	0.47 (16)	C3—C2—C8—O3	4.06 (17)
C1—N1—C2—C8	−176.14 (10)	N1—C2—C8—O3	−179.15 (10)
N1—C2—C3—O1	−179.23 (10)	C3—C2—C8—O4	−173.74 (10)
C8—C2—C3—O1	−2.66 (18)	N1—C2—C8—O4	3.06 (14)
N1—C2—C3—C4	1.43 (17)	C5—N3—C10—O5	−11.21 (19)
C8—C2—C3—C4	178.00 (10)	C5—N3—C10—O6	170.86 (10)
C1—N2—C4—O2	−178.10 (11)	C11—O6—C10—O5	5.83 (18)
C1—N2—C4—C3	1.58 (16)	C11—O6—C10—N3	−176.18 (10)
O1—C3—C4—O2	−2.06 (18)	C10—O6—C11—C12	173.06 (10)
C2—C3—C4—O2	177.35 (11)	O6—C11—C12—C17	137.37 (11)
O1—C3—C4—N2	178.27 (10)	O6—C11—C12—C13	−43.44 (15)
C2—C3—C4—N2	−2.32 (16)	C17—C12—C13—C14	0.16 (18)
C10—N3—C5—C1	63.17 (13)	C11—C12—C13—C14	−179.05 (11)
C10—N3—C5—C6	−59.82 (14)	C12—C13—C14—C15	0.83 (19)
C10—N3—C5—C7	−179.76 (10)	C13—C14—C15—C16	−0.91 (19)
N1—C1—C5—N3	−141.95 (10)	C14—C15—C16—C17	0.00 (19)
N2—C1—C5—N3	41.15 (12)	C13—C12—C17—C16	−1.07 (17)
N1—C1—C5—C6	−18.51 (14)	C11—C12—C17—C16	178.14 (11)
N2—C1—C5—C6	164.59 (10)	C15—C16—C17—C12	1.00 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O5i	0.882 (15)	2.133 (15)	2.8911 (14)	143.7 (12)
N2—H2···O2ii	0.938 (16)	1.886 (16)	2.8135 (16)	169.3 (13)
O1—H1···O3	0.918 (17)	1.788 (17)	2.6163 (14)	148.7 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O5i	0.882 (15)	2.133 (15)	2.8911 (14)	143.7 (12)
N2—H2⋯O2ii	0.938 (16)	1.886 (16)	2.8135 (16)	169.3 (13)
O1—H1⋯O3	0.918 (17)	1.788 (17)	2.6163 (14)	148.7 (16)

Symmetry codes: (i) ; (ii) .