1-(3-Chloro­benz­yl)pyrimidine-2,4(1H,3H)-dione

The title compound, C₁₁H₉ClN₂O₂, crystallizes with weak inter­molecular N—H...O hydrogen-bond inter­actions. The dihedral angle between the pyrimidine and benzene rings is 86.82 (7)°.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.037
• wR factor = 0.110
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

1-(3-chlorobenzyl)pyrimidine-2,4(1H,3H)-dione

Crystal data

C11H9ClN2O2	F(000) = 488
Mr = 236.65	Dx = 1.445 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1736 reflections
a = 10.0756 (19) Å	θ = 2.7–26.0°
b = 7.0683 (13) Å	µ = 0.34 mm^−1
c = 15.620 (3) Å	T = 294 K
β = 102.030 (3)°	Prism, colourless
V = 1088.0 (4) Å^3	0.28 × 0.20 × 0.10 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2221 independent reflections
Radiation source: fine-focus sealed tube	1394 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 26.4°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	h = −7→12
Tmin = 0.907, Tmax = 0.969	k = −8→8
5918 measured reflections	l = −19→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0524P)^2 + 0.1563P] where P = (Fo^2 + 2Fc^2)/3
2221 reflections	(Δ/σ)max = 0.001
149 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.63035 (8)	0.21632 (9)	0.85294 (4)	0.0970 (3)
O1	0.13347 (13)	−0.08508 (19)	0.47565 (8)	0.0498 (4)
O2	0.00795 (15)	0.31813 (19)	0.24907 (8)	0.0548 (4)
N1	0.07263 (15)	0.1242 (2)	0.36413 (10)	0.0399 (4)
N2	0.15853 (14)	0.2319 (2)	0.50499 (9)	0.0400 (4)
C1	0.05468 (18)	0.3026 (2)	0.32828 (12)	0.0389 (4)
C2	0.09428 (18)	0.4537 (3)	0.38883 (12)	0.0445 (5)
H2	0.0859	0.5788	0.3700	0.053*
C3	0.14343 (18)	0.4129 (3)	0.47282 (12)	0.0448 (5)
H3	0.1688	0.5126	0.5117	0.054*
C4	0.12249 (17)	0.0782 (3)	0.45048 (11)	0.0378 (4)
C5	0.21144 (19)	0.1985 (3)	0.59828 (11)	0.0490 (5)
H5A	0.1818	0.0746	0.6134	0.059*
H5B	0.1725	0.2915	0.6316	0.059*
C6	0.36380 (18)	0.2083 (2)	0.62530 (12)	0.0400 (4)
C7	0.4212 (2)	0.2093 (3)	0.71412 (12)	0.0472 (5)
H7	0.3659	0.2072	0.7550	0.057*
C8	0.5597 (2)	0.2134 (3)	0.74154 (15)	0.0578 (6)
C9	0.6438 (2)	0.2171 (3)	0.68308 (18)	0.0738 (7)
H9	0.7376	0.2193	0.7025	0.089*
C10	0.5871 (2)	0.2173 (4)	0.59539 (18)	0.0732 (7)
H10	0.6431	0.2202	0.5550	0.088*
C11	0.4478 (2)	0.2134 (3)	0.56597 (13)	0.0538 (5)
H11	0.4108	0.2141	0.5062	0.065*
H1	0.0504 (19)	0.030 (3)	0.3282 (12)	0.052 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.1285 (6)	0.0611 (4)	0.0687 (4)	0.0043 (4)	−0.0544 (4)	−0.0003 (3)
O1	0.0556 (9)	0.0449 (9)	0.0471 (8)	0.0064 (7)	0.0067 (6)	0.0111 (6)
O2	0.0777 (10)	0.0450 (8)	0.0353 (7)	0.0003 (7)	−0.0026 (7)	0.0048 (6)
N1	0.0461 (9)	0.0353 (9)	0.0355 (9)	−0.0022 (7)	0.0019 (7)	−0.0013 (7)
N2	0.0364 (8)	0.0477 (10)	0.0332 (8)	−0.0031 (7)	0.0010 (7)	0.0007 (7)
C1	0.0387 (10)	0.0379 (11)	0.0381 (10)	0.0016 (8)	0.0038 (8)	0.0044 (8)
C2	0.0497 (11)	0.0352 (11)	0.0464 (11)	−0.0024 (9)	0.0050 (9)	0.0003 (8)
C3	0.0427 (11)	0.0442 (11)	0.0465 (11)	−0.0068 (9)	0.0074 (9)	−0.0094 (9)
C4	0.0312 (9)	0.0448 (12)	0.0366 (10)	−0.0003 (8)	0.0050 (8)	0.0036 (8)
C5	0.0458 (11)	0.0700 (14)	0.0304 (10)	−0.0034 (10)	0.0063 (8)	−0.0003 (9)
C6	0.0420 (10)	0.0374 (10)	0.0381 (10)	−0.0011 (8)	0.0024 (8)	−0.0022 (8)
C7	0.0615 (13)	0.0378 (11)	0.0373 (10)	0.0009 (9)	−0.0013 (9)	−0.0007 (8)
C8	0.0670 (14)	0.0328 (11)	0.0579 (13)	0.0014 (10)	−0.0235 (12)	0.0002 (10)
C9	0.0420 (12)	0.0726 (17)	0.095 (2)	0.0013 (12)	−0.0124 (13)	0.0004 (14)
C10	0.0440 (13)	0.096 (2)	0.0791 (17)	−0.0014 (13)	0.0127 (12)	−0.0036 (14)
C11	0.0444 (12)	0.0695 (15)	0.0459 (12)	−0.0004 (10)	0.0057 (10)	−0.0034 (10)

Geometric parameters (Å, º)

Cl1—C8	1.737 (2)	C5—C6	1.507 (3)
O1—C4	1.217 (2)	C5—H5A	0.9700
O2—C1	1.234 (2)	C5—H5B	0.9700
N1—C1	1.376 (2)	C6—C11	1.380 (3)
N1—C4	1.377 (2)	C6—C7	1.387 (2)
N1—H1	0.87 (2)	C7—C8	1.372 (3)
N2—C3	1.372 (2)	C7—H7	0.9300
N2—C4	1.381 (2)	C8—C9	1.370 (3)
N2—C5	1.463 (2)	C9—C10	1.370 (3)
C1—C2	1.428 (3)	C9—H9	0.9300
C2—C3	1.334 (2)	C10—C11	1.383 (3)
C2—H2	0.9300	C10—H10	0.9300
C3—H3	0.9300	C11—H11	0.9300
C1—N1—C4	127.25 (16)	N2—C5—H5B	108.7
C1—N1—H1	116.5 (13)	C6—C5—H5B	108.7
C4—N1—H1	116.3 (13)	H5A—C5—H5B	107.6
C3—N2—C4	120.86 (15)	C11—C6—C7	119.05 (18)
C3—N2—C5	120.32 (15)	C11—C6—C5	123.02 (17)
C4—N2—C5	118.81 (15)	C7—C6—C5	117.92 (17)
O2—C1—N1	118.70 (16)	C8—C7—C6	119.8 (2)
O2—C1—C2	126.39 (17)	C8—C7—H7	120.1
N1—C1—C2	114.91 (16)	C6—C7—H7	120.1
C3—C2—C1	119.02 (18)	C9—C8—C7	121.5 (2)
C3—C2—H2	120.5	C9—C8—Cl1	119.08 (18)
C1—C2—H2	120.5	C7—C8—Cl1	119.4 (2)
C2—C3—N2	123.51 (17)	C8—C9—C10	118.6 (2)
C2—C3—H3	118.2	C8—C9—H9	120.7
N2—C3—H3	118.2	C10—C9—H9	120.7
O1—C4—N1	122.04 (17)	C9—C10—C11	121.0 (2)
O1—C4—N2	123.52 (16)	C9—C10—H10	119.5
N1—C4—N2	114.44 (16)	C11—C10—H10	119.5
N2—C5—C6	114.22 (15)	C6—C11—C10	120.0 (2)
N2—C5—H5A	108.7	C6—C11—H11	120.0
C6—C5—H5A	108.7	C10—C11—H11	120.0
C4—N1—C1—O2	−179.72 (17)	C4—N2—C5—C6	99.57 (19)
C4—N1—C1—C2	0.6 (3)	N2—C5—C6—C11	−11.3 (3)
O2—C1—C2—C3	−179.92 (18)	N2—C5—C6—C7	169.68 (16)
N1—C1—C2—C3	−0.3 (3)	C11—C6—C7—C8	−0.6 (3)
C1—C2—C3—N2	0.0 (3)	C5—C6—C7—C8	178.40 (17)
C4—N2—C3—C2	0.0 (3)	C6—C7—C8—C9	0.1 (3)
C5—N2—C3—C2	−179.12 (17)	C6—C7—C8—Cl1	179.55 (14)
C1—N1—C4—O1	179.47 (17)	C7—C8—C9—C10	0.3 (4)
C1—N1—C4—N2	−0.6 (3)	Cl1—C8—C9—C10	−179.12 (18)
C3—N2—C4—O1	−179.81 (17)	C8—C9—C10—C11	−0.2 (4)
C5—N2—C4—O1	−0.7 (3)	C7—C6—C11—C10	0.7 (3)
C3—N2—C4—N1	0.3 (2)	C5—C6—C11—C10	−178.3 (2)
C5—N2—C4—N1	179.39 (15)	C9—C10—C11—C6	−0.3 (4)
C3—N2—C5—C6	−81.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^i	0.87 (2)	1.94 (2)	2.805 (2)	176.9 (18)

Symmetry code: (i) −x, y−1/2, −z+1/2.