Methyl 2-[2-(benzyl-oxycarbonyl-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), a pyrimidine derivative, the dihedral angle between the benzene and pyrimidine rings is 52.26 (12)°. The carboxyl-ate unit is twisted with respect to the pyrimidine ring, making a dihedral angle of 12.33 (7)°. In the crystal, mol-ecules are linked by a pair of O-H⋯O hydrogen bonds, forming an inversion dimer. The dimers are stacked into columns along the b axis through weak C-H⋯O inter-actions.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For background to and applications of pyrimidine derivatives, see: Cheng & Roth (1971 ▶); Cox (1968 ▶); Eussell (1945 ▶); Jain et al. (2006 ▶); Shinogi (1959 ▶); Tani et al. (1979 ▶).

Experimental

Crystal data

C18H21N3O6

M = 375.38

Monoclinic,

a = 16.5226 (2) Å

b = 8.5717 (1) Å

c = 13.0944 (2) Å

β = 97.236 (1)°

V = 1839.75 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 297 K

0.57 × 0.52 × 0.39 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.944, T max = 0.961

20111 measured reflections

5348 independent reflections

4087 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.164

S = 1.04

5348 reflections

256 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.52 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681005467X/is2653sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681005467X/is2653Isup2.hkl

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

C18H21N3O6	F(000) = 792
Mr = 375.38	Dx = 1.355 Mg m−3
Monoclinic, P21/c	Melting point = 391–393 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 16.5226 (2) Å	Cell parameters from 5348 reflections
b = 8.5717 (1) Å	θ = 2.5–30.0°
c = 13.0944 (2) Å	µ = 0.10 mm−1
β = 97.236 (1)°	T = 297 K
V = 1839.75 (4) Å3	Block, colorless
Z = 4	0.57 × 0.52 × 0.39 mm

Bruker APEXII CCD area-detector diffractometer	5348 independent reflections
Radiation source: sealed tube	4087 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 30.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −23→22
Tmin = 0.944, Tmax = 0.961	k = −8→12
20111 measured reflections	l = −18→18

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0839P)2 + 0.5187P] where P = (Fo2 + 2Fc2)/3
5348 reflections	(Δ/σ)max = 0.001
256 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

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
O1	0.33157 (8)	0.66001 (18)	0.07370 (11)	0.0657 (4)
O2	0.24087 (8)	0.48066 (17)	0.11686 (10)	0.0576 (3)
O3	0.06818 (6)	0.74259 (11)	−0.14162 (9)	0.0416 (3)
O4	−0.06047 (6)	0.56031 (12)	−0.13886 (9)	0.0417 (3)
O5	−0.10852 (6)	0.26969 (13)	−0.11206 (10)	0.0473 (3)
O6	−0.01903 (6)	0.07581 (11)	−0.11913 (8)	0.0393 (2)
N1	0.30737 (7)	0.45068 (16)	−0.02407 (11)	0.0407 (3)
N2	0.15729 (7)	0.53687 (13)	−0.11038 (9)	0.0355 (3)
N3	0.10782 (7)	0.27843 (13)	−0.09593 (9)	0.0335 (2)
C1	0.43521 (17)	0.8804 (4)	0.2532 (3)	0.0946 (9)
H1A	0.4369	0.9541	0.2015	0.114*
C2	0.49368 (19)	0.8838 (5)	0.3419 (3)	0.1240 (13)
H2A	0.5334	0.9611	0.3500	0.149*
C3	0.49077 (19)	0.7724 (5)	0.4147 (3)	0.1109 (12)
H3A	0.5300	0.7721	0.4723	0.133*
C4	0.43242 (19)	0.6625 (5)	0.4054 (2)	0.1040 (10)
H4A	0.4310	0.5876	0.4566	0.125*
C5	0.37474 (15)	0.6607 (3)	0.3200 (2)	0.0802 (7)
H5A	0.3342	0.5848	0.3144	0.096*
C6	0.37579 (10)	0.7669 (2)	0.24422 (15)	0.0554 (4)
C7	0.31165 (14)	0.7682 (3)	0.15168 (18)	0.0690 (6)
H7A	0.2593	0.7402	0.1727	0.083*
H7B	0.3070	0.8727	0.1230	0.083*
C8	0.28785 (9)	0.5255 (2)	0.06047 (12)	0.0438 (3)
C9	0.25579 (8)	0.32633 (17)	−0.07422 (12)	0.0402 (3)
C10	0.16670 (8)	0.38177 (15)	−0.09313 (10)	0.0334 (3)
C11	0.08266 (8)	0.59052 (15)	−0.12577 (10)	0.0331 (3)
C12	0.01324 (8)	0.49250 (15)	−0.12617 (10)	0.0319 (3)
C13	0.03020 (8)	0.33494 (15)	−0.11279 (10)	0.0306 (3)
C14	−0.03910 (8)	0.22435 (15)	−0.11428 (10)	0.0327 (3)
C15	−0.08544 (9)	−0.03516 (18)	−0.11987 (13)	0.0428 (3)
H15A	−0.0688	−0.1342	−0.1443	0.064*
H15B	−0.1320	0.0021	−0.1645	0.064*
H15C	−0.0995	−0.0467	−0.0513	0.064*
C16	0.28446 (11)	0.2973 (3)	−0.17910 (16)	0.0620 (5)
H16A	0.2781	0.3910	−0.2195	0.093*
H16B	0.2524	0.2154	−0.2141	0.093*
H16C	0.3409	0.2672	−0.1696	0.093*
C17	0.26450 (10)	0.1795 (2)	−0.00690 (18)	0.0621 (5)
H17A	0.2431	0.1996	0.0567	0.093*
H17B	0.3211	0.1517	0.0072	0.093*
H17C	0.2348	0.0953	−0.0424	0.093*
C18	0.13886 (10)	0.84324 (18)	−0.13387 (14)	0.0459 (4)
H18A	0.1215	0.9500	−0.1412	0.069*
H18B	0.1714	0.8175	−0.1873	0.069*
H18C	0.1706	0.8291	−0.0679	0.069*
H1N1	0.3337 (13)	0.501 (3)	−0.0634 (16)	0.056 (6)*
H1O4	−0.0985 (14)	0.492 (3)	−0.1310 (16)	0.061 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0588 (8)	0.0660 (9)	0.0713 (8)	−0.0192 (6)	0.0041 (6)	−0.0211 (7)
O2	0.0530 (7)	0.0649 (8)	0.0557 (7)	0.0042 (6)	0.0103 (6)	0.0081 (6)
O3	0.0391 (5)	0.0268 (5)	0.0573 (6)	−0.0004 (4)	−0.0006 (4)	0.0011 (4)
O4	0.0325 (5)	0.0345 (5)	0.0567 (6)	0.0049 (4)	0.0008 (4)	0.0005 (4)
O5	0.0312 (5)	0.0390 (6)	0.0718 (8)	0.0009 (4)	0.0068 (5)	0.0000 (5)
O6	0.0327 (5)	0.0293 (5)	0.0552 (6)	−0.0027 (4)	0.0033 (4)	0.0006 (4)
N1	0.0304 (6)	0.0433 (7)	0.0474 (7)	−0.0052 (5)	0.0014 (5)	0.0011 (5)
N2	0.0333 (5)	0.0301 (5)	0.0416 (6)	−0.0014 (4)	−0.0004 (4)	−0.0009 (4)
N3	0.0304 (5)	0.0298 (5)	0.0394 (6)	0.0008 (4)	0.0003 (4)	−0.0007 (4)
C1	0.0813 (16)	0.0911 (19)	0.111 (2)	−0.0374 (15)	0.0084 (15)	−0.0063 (16)
C2	0.0691 (17)	0.151 (3)	0.147 (3)	−0.053 (2)	−0.0074 (19)	−0.038 (3)
C3	0.0686 (16)	0.165 (4)	0.093 (2)	0.002 (2)	−0.0162 (15)	−0.040 (2)
C4	0.089 (2)	0.142 (3)	0.0788 (17)	0.013 (2)	0.0018 (14)	0.0011 (18)
C5	0.0657 (13)	0.0840 (17)	0.0898 (16)	−0.0073 (12)	0.0052 (12)	0.0038 (13)
C6	0.0419 (8)	0.0564 (10)	0.0666 (11)	−0.0045 (7)	0.0025 (8)	−0.0181 (9)
C7	0.0615 (11)	0.0586 (11)	0.0818 (14)	0.0012 (9)	−0.0102 (10)	−0.0192 (10)
C8	0.0332 (7)	0.0502 (8)	0.0455 (8)	0.0006 (6)	−0.0050 (6)	0.0024 (6)
C9	0.0293 (6)	0.0348 (7)	0.0553 (8)	0.0005 (5)	0.0009 (6)	−0.0013 (6)
C10	0.0308 (6)	0.0302 (6)	0.0381 (6)	0.0006 (5)	−0.0001 (5)	−0.0010 (5)
C11	0.0362 (6)	0.0278 (6)	0.0341 (6)	0.0007 (5)	−0.0004 (5)	−0.0010 (5)
C12	0.0318 (6)	0.0300 (6)	0.0324 (6)	0.0028 (5)	−0.0011 (5)	−0.0024 (5)
C13	0.0295 (6)	0.0296 (6)	0.0317 (6)	−0.0005 (5)	0.0002 (4)	−0.0009 (5)
C14	0.0319 (6)	0.0313 (6)	0.0339 (6)	0.0003 (5)	0.0000 (5)	0.0000 (5)
C15	0.0394 (7)	0.0344 (7)	0.0539 (8)	−0.0075 (6)	0.0028 (6)	0.0019 (6)
C16	0.0462 (9)	0.0700 (12)	0.0707 (12)	0.0050 (9)	0.0103 (8)	−0.0242 (10)
C17	0.0386 (8)	0.0397 (8)	0.1037 (15)	0.0030 (7)	−0.0084 (9)	0.0170 (9)
C18	0.0458 (8)	0.0310 (7)	0.0596 (9)	−0.0061 (6)	0.0016 (7)	0.0005 (6)

O1—C8	1.360 (2)	C4—H4A	0.9300
O1—C7	1.448 (3)	C5—C6	1.349 (3)
O2—C8	1.200 (2)	C5—H5A	0.9300
O3—C11	1.3368 (16)	C6—C7	1.506 (3)
O3—C18	1.4452 (18)	C7—H7A	0.9700
O4—C12	1.3408 (16)	C7—H7B	0.9700
O4—H1O4	0.88 (2)	C9—C16	1.529 (2)
O5—C14	1.2149 (17)	C9—C17	1.533 (2)
O6—C14	1.3193 (16)	C9—C10	1.5370 (18)
O6—C15	1.4513 (17)	C11—C12	1.4213 (19)
N1—C8	1.353 (2)	C12—C13	1.3860 (18)
N1—C9	1.4672 (19)	C13—C14	1.4847 (18)
N1—H1N1	0.83 (2)	C15—H15A	0.9600
N2—C11	1.3077 (17)	C15—H15B	0.9600
N2—C10	1.3542 (17)	C15—H15C	0.9600
N3—C10	1.3127 (17)	C16—H16A	0.9600
N3—C13	1.3627 (16)	C16—H16B	0.9600
C1—C6	1.376 (3)	C16—H16C	0.9600
C1—C2	1.414 (5)	C17—H17A	0.9600
C1—H1A	0.9300	C17—H17B	0.9600
C2—C3	1.354 (5)	C17—H17C	0.9600
C2—H2A	0.9300	C18—H18A	0.9600
C3—C4	1.343 (5)	C18—H18B	0.9600
C3—H3A	0.9300	C18—H18C	0.9600
C4—C5	1.375 (4)
C8—O1—C7	117.95 (16)	C17—C9—C10	111.42 (13)
C11—O3—C18	116.35 (11)	N3—C10—N2	126.07 (12)
C12—O4—H1O4	110.4 (15)	N3—C10—C9	119.16 (12)
C14—O6—C15	116.01 (11)	N2—C10—C9	114.70 (12)
C8—N1—C9	121.72 (13)	N2—C11—O3	120.91 (12)
C8—N1—H1N1	117.3 (15)	N2—C11—C12	122.52 (12)
C9—N1—H1N1	114.6 (15)	O3—C11—C12	116.57 (12)
C11—N2—C10	117.20 (12)	O4—C12—C13	127.17 (12)
C10—N3—C13	116.34 (11)	O4—C12—C11	117.66 (12)
C6—C1—C2	119.4 (3)	C13—C12—C11	115.17 (12)
C6—C1—H1A	120.3	N3—C13—C12	122.55 (12)
C2—C1—H1A	120.3	N3—C13—C14	118.93 (11)
C3—C2—C1	118.8 (3)	C12—C13—C14	118.50 (11)
C3—C2—H2A	120.6	O5—C14—O6	123.62 (13)
C1—C2—H2A	120.6	O5—C14—C13	121.63 (12)
C4—C3—C2	121.3 (3)	O6—C14—C13	114.75 (11)
C4—C3—H3A	119.3	O6—C15—H15A	109.5
C2—C3—H3A	119.3	O6—C15—H15B	109.5
C3—C4—C5	119.9 (3)	H15A—C15—H15B	109.5
C3—C4—H4A	120.1	O6—C15—H15C	109.5
C5—C4—H4A	120.1	H15A—C15—H15C	109.5
C6—C5—C4	121.3 (3)	H15B—C15—H15C	109.5
C6—C5—H5A	119.4	C9—C16—H16A	109.5
C4—C5—H5A	119.4	C9—C16—H16B	109.5
C5—C6—C1	119.3 (2)	H16A—C16—H16B	109.5
C5—C6—C7	121.61 (19)	C9—C16—H16C	109.5
C1—C6—C7	119.1 (2)	H16A—C16—H16C	109.5
O1—C7—C6	111.30 (17)	H16B—C16—H16C	109.5
O1—C7—H7A	109.4	C9—C17—H17A	109.5
C6—C7—H7A	109.4	C9—C17—H17B	109.5
O1—C7—H7B	109.4	H17A—C17—H17B	109.5
C6—C7—H7B	109.4	C9—C17—H17C	109.5
H7A—C7—H7B	108.0	H17A—C17—H17C	109.5
O2—C8—N1	126.21 (16)	H17B—C17—H17C	109.5
O2—C8—O1	124.59 (16)	O3—C18—H18A	109.5
N1—C8—O1	109.19 (14)	O3—C18—H18B	109.5
N1—C9—C16	106.99 (13)	H18A—C18—H18B	109.5
N1—C9—C17	109.39 (13)	O3—C18—H18C	109.5
C16—C9—C17	111.45 (16)	H18A—C18—H18C	109.5
N1—C9—C10	109.75 (11)	H18B—C18—H18C	109.5
C16—C9—C10	107.73 (12)
C6—C1—C2—C3	1.6 (5)	C17—C9—C10—N3	−30.53 (19)
C1—C2—C3—C4	−1.8 (6)	N1—C9—C10—N2	31.13 (17)
C2—C3—C4—C5	0.7 (6)	C16—C9—C10—N2	−85.01 (16)
C3—C4—C5—C6	0.6 (5)	C17—C9—C10—N2	152.45 (14)
C4—C5—C6—C1	−0.8 (4)	C10—N2—C11—O3	178.86 (12)
C4—C5—C6—C7	−178.5 (2)	C10—N2—C11—C12	−0.8 (2)
C2—C1—C6—C5	−0.3 (4)	C18—O3—C11—N2	−3.98 (19)
C2—C1—C6—C7	177.4 (3)	C18—O3—C11—C12	175.74 (12)
C8—O1—C7—C6	106.6 (2)	N2—C11—C12—O4	177.56 (12)
C5—C6—C7—O1	−84.3 (3)	O3—C11—C12—O4	−2.16 (18)
C1—C6—C7—O1	98.0 (3)	N2—C11—C12—C13	−2.25 (19)
C9—N1—C8—O2	18.1 (2)	O3—C11—C12—C13	178.04 (12)
C9—N1—C8—O1	−163.27 (13)	C10—N3—C13—C12	−0.14 (19)
C7—O1—C8—O2	−9.7 (2)	C10—N3—C13—C14	−178.53 (11)
C7—O1—C8—N1	171.67 (15)	O4—C12—C13—N3	−177.02 (12)
C8—N1—C9—C16	166.62 (15)	C11—C12—C13—N3	2.76 (19)
C8—N1—C9—C17	−72.52 (18)	O4—C12—C13—C14	1.4 (2)
C8—N1—C9—C10	50.01 (18)	C11—C12—C13—C14	−178.85 (11)
C13—N3—C10—N2	−3.5 (2)	C15—O6—C14—O5	−1.1 (2)
C13—N3—C10—C9	179.89 (12)	C15—O6—C14—C13	179.53 (11)
C11—N2—C10—N3	4.0 (2)	N3—C13—C14—O5	167.78 (13)
C11—N2—C10—C9	−179.24 (12)	C12—C13—C14—O5	−10.7 (2)
N1—C9—C10—N3	−151.85 (13)	N3—C13—C14—O6	−12.83 (17)
C16—C9—C10—N3	92.00 (17)	C12—C13—C14—O6	168.72 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1O4···O5	0.87 (2)	1.93 (3)	2.6513 (15)	139 (2)
O4—H1O4···O2i	0.87 (2)	2.39 (2)	3.0508 (17)	132 (2)
C7—H7A···O5i	0.97	2.52	3.347 (3)	143
C15—H15A···O3ii	0.96	2.49	3.2148 (18)	132
C17—H17A···O2	0.96	2.54	3.099 (2)	117

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H1O4⋯O5	0.87 (2)	1.93 (3)	2.6513 (15)	139 (2)
O4—H1O4⋯O2i	0.87 (2)	2.39 (2)	3.0508 (17)	132 (2)
C7—H7A⋯O5i	0.97	2.52	3.347 (3)	143
C15—H15A⋯O3ii	0.96	2.49	3.2148 (18)	132
C17—H17A⋯O2	0.96	2.54	3.099 (2)	117

Symmetry codes: (i) ; (ii) .