6-Isopropoxy-5-iso­propyl­pyrimidine-2,4(1H,3H)-dione

Two mol­ecules of the title compound, C₁₀H₁₆N₂O₃, constitute the asymmetric unit. The mol­ecules form a two-dimensional hydrogen-bonded sheet in the ab plane.

Key indicators

• Single-crystal X-ray study
• T = 163 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.077
• wR factor = 0.198
• Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.587     1.000
            Tmin' and Tmax expected:      0.937     0.991
            RR' =      0.621
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.62

Alert level C
DIFMX01_ALERT_2_C  The maximum difference density is > 0.1*ZMAX*0.75
            _refine_diff_density_max given =      0.605
            Test value =      0.600
DIFMX02_ALERT_1_C  The minimum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.91
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.70 mm
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............       0.61 e/A   3
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

6-Isopropoxy-5-isopropylpyrimidine-2,4(1H,3H)-dione

Crystal data

C10H16N2O3	Z = 4
Mr = 212.25	F(000) = 456
Triclinic, P1	Dx = 1.254 Mg m^−3
Hall symbol: -P 1	Melting point: 501 K
a = 8.769 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.178 (8) Å	Cell parameters from 2889 reflections
c = 12.418 (9) Å	θ = 4.8–52.0°
α = 71.074 (9)°	µ = 0.09 mm^−1
β = 77.684 (9)°	T = 163 K
γ = 88.014 (9)°	Needle, colourless
V = 1124.1 (13) Å^3	0.70 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer	4703 independent reflections
Radiation source: fine-focus sealed tube	2497 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.068
Detector resolution: 8.192 pixels mm^-1	θmax = 27.5°, θmin = 2.2°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 1999)	k = −7→14
Tmin = 0.587, Tmax = 1.000	l = −16→15
14452 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.077	H-atom parameters constrained
wR(F^2) = 0.198	w = 1/[σ^2(Fo^2) + (0.1178P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.91	(Δ/σ)max < 0.001
4703 reflections	Δρmax = 0.61 e Å^−3
280 parameters	Δρmin = −0.45 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.032 (5)

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
N1	0.6073 (3)	0.7615 (2)	0.12465 (19)	0.0259 (6)
H1A	0.5443	0.7030	0.1227	0.031*
C2	0.7496 (3)	0.7875 (3)	0.0468 (2)	0.0261 (7)
O2	0.7881 (2)	0.73286 (19)	−0.02646 (17)	0.0323 (5)
N3	0.8405 (3)	0.8774 (2)	0.0565 (2)	0.0267 (6)
H3A	0.9331	0.8947	0.0094	0.032*
C4	0.7998 (3)	0.9451 (3)	0.1348 (2)	0.0261 (7)
O4	0.8924 (2)	1.02879 (19)	0.12908 (17)	0.0330 (5)
C5	0.6491 (3)	0.9141 (2)	0.2140 (2)	0.0245 (7)
C6	0.5595 (3)	0.8228 (3)	0.2051 (2)	0.0245 (7)
O6	0.4186 (2)	0.78599 (18)	0.27840 (16)	0.0283 (5)
C7	0.5918 (4)	0.9834 (3)	0.3016 (3)	0.0359 (8)
H7A	0.4859	0.9461	0.3463	0.043*
C8	0.5718 (5)	1.1240 (3)	0.2388 (4)	0.0568 (11)
H8A	0.5037	1.1322	0.1838	0.085*
H8B	0.6741	1.1647	0.1963	0.085*
H8C	0.5249	1.1650	0.2962	0.085*
C9	0.6960 (4)	0.9629 (4)	0.3897 (3)	0.0572 (11)
H9A	0.7003	0.8721	0.4305	0.086*
H9B	0.6530	1.0059	0.4463	0.086*
H9C	0.8015	0.9975	0.3489	0.086*
C10	0.2868 (3)	0.7628 (3)	0.2300 (3)	0.0287 (7)
H10A	0.3090	0.6893	0.2005	0.034*
C11	0.2616 (4)	0.8789 (3)	0.1315 (3)	0.0427 (9)
H11A	0.3562	0.8992	0.0694	0.064*
H11B	0.2386	0.9505	0.1607	0.064*
H11C	0.1737	0.8620	0.1005	0.064*
C12	0.1486 (4)	0.7296 (3)	0.3315 (3)	0.0436 (9)
H12A	0.1722	0.6565	0.3942	0.065*
H12B	0.0572	0.7087	0.3065	0.065*
H12C	0.1266	0.8019	0.3599	0.065*
N1'	0.9181 (3)	0.3592 (2)	0.0980 (2)	0.0266 (6)
H1D	1.0097	0.3248	0.0894	0.032*
C2'	0.8376 (3)	0.3844 (3)	0.0087 (2)	0.0268 (7)
O2'	0.8916 (2)	0.3626 (2)	−0.08229 (17)	0.0355 (6)
N3'	0.6948 (3)	0.4372 (2)	0.0306 (2)	0.0261 (6)
H3D	0.6385	0.4516	−0.0228	0.031*
C4'	0.6317 (3)	0.4698 (3)	0.1293 (2)	0.0251 (7)
O4'	0.5010 (2)	0.52323 (18)	0.13321 (16)	0.0279 (5)
C5'	0.7186 (3)	0.4424 (2)	0.2188 (2)	0.0238 (7)
C6'	0.8604 (3)	0.3860 (3)	0.1996 (2)	0.0254 (7)
O6'	0.9424 (2)	0.3556 (2)	0.28353 (17)	0.0334 (5)
C7'	0.6545 (3)	0.4724 (3)	0.3310 (2)	0.0278 (7)
H7D	0.5573	0.5200	0.3200	0.033*
C8'	0.6063 (4)	0.3530 (3)	0.4364 (3)	0.0389 (8)
H8D	0.5269	0.3039	0.4221	0.058*
H8E	0.5634	0.3770	0.5058	0.058*
H8F	0.6978	0.3016	0.4489	0.058*
C9'	0.7644 (4)	0.5585 (3)	0.3554 (3)	0.0373 (8)
H9D	0.7088	0.5896	0.4177	0.056*
H9E	0.8010	0.6303	0.2846	0.056*
H9F	0.8541	0.5108	0.3795	0.056*
C10'	1.1033 (3)	0.3099 (3)	0.2692 (3)	0.0308 (7)
H10D	1.1592	0.3456	0.1859	0.037*
C11'	1.0971 (4)	0.1684 (3)	0.3060 (3)	0.0442 (9)
H11D	1.0420	0.1408	0.2568	0.066*
H11E	1.0418	0.1339	0.3875	0.066*
H11F	1.2037	0.1377	0.2976	0.066*
C12'	1.1786 (4)	0.3621 (3)	0.3443 (3)	0.0422 (9)
H12D	1.1760	0.4547	0.3171	0.063*
H12E	1.2873	0.3365	0.3390	0.063*
H12F	1.1213	0.3289	0.4255	0.063*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0242 (13)	0.0291 (13)	0.0214 (13)	−0.0025 (11)	0.0009 (11)	−0.0074 (10)
C2	0.0255 (16)	0.0267 (15)	0.0205 (16)	0.0046 (13)	−0.0038 (13)	−0.0014 (12)
O2	0.0294 (12)	0.0380 (12)	0.0280 (12)	0.0011 (10)	0.0006 (10)	−0.0130 (10)
N3	0.0222 (13)	0.0292 (13)	0.0236 (14)	−0.0030 (11)	0.0036 (11)	−0.0069 (10)
C4	0.0304 (17)	0.0245 (15)	0.0192 (15)	0.0013 (13)	−0.0054 (13)	−0.0014 (12)
O4	0.0301 (12)	0.0352 (12)	0.0293 (12)	−0.0080 (10)	0.0030 (10)	−0.0097 (9)
C5	0.0278 (16)	0.0237 (14)	0.0173 (15)	−0.0028 (12)	0.0007 (13)	−0.0034 (11)
C6	0.0259 (16)	0.0266 (15)	0.0145 (15)	0.0014 (13)	0.0004 (13)	−0.0012 (11)
O6	0.0241 (11)	0.0385 (12)	0.0185 (11)	−0.0047 (9)	0.0005 (9)	−0.0066 (9)
C7	0.0301 (18)	0.0425 (19)	0.0362 (19)	−0.0095 (15)	0.0075 (15)	−0.0224 (15)
C8	0.052 (2)	0.041 (2)	0.071 (3)	−0.0031 (18)	0.014 (2)	−0.0274 (19)
C9	0.046 (2)	0.094 (3)	0.035 (2)	−0.016 (2)	0.0049 (19)	−0.032 (2)
C10	0.0232 (16)	0.0363 (17)	0.0251 (16)	−0.0027 (13)	−0.0044 (13)	−0.0080 (13)
C11	0.0329 (19)	0.053 (2)	0.0327 (19)	0.0027 (16)	−0.0044 (16)	−0.0025 (16)
C12	0.0269 (18)	0.060 (2)	0.037 (2)	−0.0088 (16)	0.0018 (16)	−0.0112 (17)
N1'	0.0241 (13)	0.0333 (13)	0.0209 (13)	0.0051 (11)	−0.0034 (11)	−0.0079 (10)
C2'	0.0288 (17)	0.0279 (16)	0.0210 (16)	−0.0010 (13)	−0.0033 (14)	−0.0053 (12)
O2'	0.0351 (13)	0.0496 (14)	0.0224 (12)	0.0056 (10)	−0.0035 (10)	−0.0145 (10)
N3'	0.0267 (14)	0.0312 (13)	0.0211 (13)	0.0041 (11)	−0.0075 (11)	−0.0084 (10)
C4'	0.0310 (17)	0.0222 (14)	0.0184 (15)	−0.0017 (13)	−0.0014 (13)	−0.0038 (11)
O4'	0.0250 (12)	0.0326 (11)	0.0240 (11)	0.0056 (9)	−0.0055 (9)	−0.0067 (9)
C5'	0.0271 (16)	0.0247 (15)	0.0182 (15)	0.0012 (12)	−0.0038 (13)	−0.0056 (11)
C6'	0.0271 (17)	0.0299 (15)	0.0161 (15)	−0.0002 (13)	−0.0029 (13)	−0.0041 (12)
O6'	0.0262 (12)	0.0510 (13)	0.0215 (11)	0.0112 (10)	−0.0059 (9)	−0.0102 (9)
C7'	0.0249 (16)	0.0367 (17)	0.0193 (16)	0.0042 (13)	−0.0006 (13)	−0.0086 (13)
C8'	0.0340 (19)	0.056 (2)	0.0191 (17)	0.0015 (16)	−0.0013 (14)	−0.0047 (14)
C9'	0.039 (2)	0.0462 (19)	0.0300 (18)	0.0056 (16)	−0.0091 (16)	−0.0157 (15)
C10'	0.0232 (17)	0.0409 (18)	0.0258 (17)	0.0070 (14)	−0.0024 (14)	−0.0099 (14)
C11'	0.045 (2)	0.0414 (19)	0.042 (2)	0.0084 (16)	−0.0062 (18)	−0.0099 (16)
C12'	0.0320 (19)	0.061 (2)	0.035 (2)	0.0024 (17)	−0.0080 (16)	−0.0167 (17)

Geometric parameters (Å, º)

N1—C6	1.375 (4)	N1'—C6'	1.377 (4)
N1—C2	1.380 (4)	N1'—C2'	1.387 (4)
N1—H1A	0.8800	N1'—H1D	0.8800
C2—O2	1.237 (3)	C2'—O2'	1.226 (3)
C2—N3	1.354 (4)	C2'—N3'	1.378 (4)
N3—C4	1.398 (4)	N3'—C4'	1.388 (4)
N3—H3A	0.8800	N3'—H3D	0.8800
C4—O4	1.235 (3)	C4'—O4'	1.273 (3)
C4—C5	1.446 (4)	C4'—C5'	1.426 (4)
C5—C6	1.355 (4)	C5'—C6'	1.385 (4)
C5—C7	1.524 (4)	C5'—C7'	1.525 (4)
C6—O6	1.355 (3)	C6'—O6'	1.339 (3)
O6—C10	1.478 (3)	O6'—C10'	1.478 (4)
C7—C9	1.528 (5)	C7'—C9'	1.523 (4)
C7—C8	1.535 (5)	C7'—C8'	1.531 (4)
C7—H7A	1.0000	C7'—H7D	1.0000
C8—H8A	0.9800	C8'—H8D	0.9800
C8—H8B	0.9800	C8'—H8E	0.9800
C8—H8C	0.9800	C8'—H8F	0.9800
C9—H9A	0.9800	C9'—H9D	0.9800
C9—H9B	0.9800	C9'—H9E	0.9800
C9—H9C	0.9800	C9'—H9F	0.9800
C10—C12	1.508 (4)	C10'—C11'	1.497 (4)
C10—C11	1.515 (4)	C10'—C12'	1.513 (4)
C10—H10A	1.0000	C10'—H10D	1.0000
C11—H11A	0.9800	C11'—H11D	0.9800
C11—H11B	0.9800	C11'—H11E	0.9800
C11—H11C	0.9800	C11'—H11F	0.9800
C12—H12A	0.9800	C12'—H12D	0.9800
C12—H12B	0.9800	C12'—H12E	0.9800
C12—H12C	0.9800	C12'—H12F	0.9800
C6—N1—C2	123.0 (2)	C6'—N1'—C2'	122.7 (2)
C6—N1—H1A	118.5	C6'—N1'—H1D	118.6
C2—N1—H1A	118.5	C2'—N1'—H1D	118.6
O2—C2—N3	123.5 (3)	O2'—C2'—N3'	123.6 (3)
O2—C2—N1	121.6 (3)	O2'—C2'—N1'	122.1 (3)
N3—C2—N1	114.9 (3)	N3'—C2'—N1'	114.3 (3)
C2—N3—C4	125.7 (3)	C2'—N3'—C4'	125.9 (2)
C2—N3—H3A	117.2	C2'—N3'—H3D	117.0
C4—N3—H3A	117.2	C4'—N3'—H3D	117.0
O4—C4—N3	118.0 (3)	O4'—C4'—N3'	117.8 (2)
O4—C4—C5	124.9 (3)	O4'—C4'—C5'	124.5 (3)
N3—C4—C5	117.0 (3)	N3'—C4'—C5'	117.8 (3)
C6—C5—C4	117.1 (3)	C6'—C5'—C4'	117.0 (3)
C6—C5—C7	121.4 (3)	C6'—C5'—C7'	122.3 (3)
C4—C5—C7	121.5 (2)	C4'—C5'—C7'	120.7 (3)
O6—C6—C5	120.6 (3)	O6'—C6'—N1'	119.4 (3)
O6—C6—N1	117.0 (2)	O6'—C6'—C5'	118.4 (3)
C5—C6—N1	122.4 (3)	N1'—C6'—C5'	122.2 (3)
C6—O6—C10	118.4 (2)	C6'—O6'—C10'	124.0 (2)
C5—C7—C9	112.0 (3)	C9'—C7'—C5'	113.2 (2)
C5—C7—C8	110.7 (3)	C9'—C7'—C8'	111.0 (2)
C9—C7—C8	112.5 (3)	C5'—C7'—C8'	112.4 (2)
C5—C7—H7A	107.1	C9'—C7'—H7D	106.6
C9—C7—H7A	107.1	C5'—C7'—H7D	106.6
C8—C7—H7A	107.1	C8'—C7'—H7D	106.6
C7—C8—H8A	109.5	C7'—C8'—H8D	109.5
C7—C8—H8B	109.5	C7'—C8'—H8E	109.5
H8A—C8—H8B	109.5	H8D—C8'—H8E	109.5
C7—C8—H8C	109.5	C7'—C8'—H8F	109.5
H8A—C8—H8C	109.5	H8D—C8'—H8F	109.5
H8B—C8—H8C	109.5	H8E—C8'—H8F	109.5
C7—C9—H9A	109.5	C7'—C9'—H9D	109.5
C7—C9—H9B	109.5	C7'—C9'—H9E	109.5
H9A—C9—H9B	109.5	H9D—C9'—H9E	109.5
C7—C9—H9C	109.5	C7'—C9'—H9F	109.5
H9A—C9—H9C	109.5	H9D—C9'—H9F	109.5
H9B—C9—H9C	109.5	H9E—C9'—H9F	109.5
O6—C10—C12	105.0 (2)	O6'—C10'—C11'	109.2 (3)
O6—C10—C11	110.5 (2)	O6'—C10'—C12'	104.3 (2)
C12—C10—C11	112.5 (3)	C11'—C10'—C12'	113.7 (3)
O6—C10—H10A	109.6	O6'—C10'—H10D	109.8
C12—C10—H10A	109.6	C11'—C10'—H10D	109.8
C11—C10—H10A	109.6	C12'—C10'—H10D	109.8
C10—C11—H11A	109.5	C10'—C11'—H11D	109.5
C10—C11—H11B	109.5	C10'—C11'—H11E	109.5
H11A—C11—H11B	109.5	H11D—C11'—H11E	109.5
C10—C11—H11C	109.5	C10'—C11'—H11F	109.5
H11A—C11—H11C	109.5	H11D—C11'—H11F	109.5
H11B—C11—H11C	109.5	H11E—C11'—H11F	109.5
C10—C12—H12A	109.5	C10'—C12'—H12D	109.5
C10—C12—H12B	109.5	C10'—C12'—H12E	109.5
H12A—C12—H12B	109.5	H12D—C12'—H12E	109.5
C10—C12—H12C	109.5	C10'—C12'—H12F	109.5
H12A—C12—H12C	109.5	H12D—C12'—H12F	109.5
H12B—C12—H12C	109.5	H12E—C12'—H12F	109.5
C6—N1—C2—O2	−178.4 (3)	O4'—C4'—C5'—C6'	−178.8 (3)
C6—N1—C2—N3	0.9 (4)	N3'—C4'—C5'—C6'	0.5 (4)
O2—C2—N3—C4	177.5 (3)	O4'—C4'—C5'—C7'	2.3 (4)
N1—C2—N3—C4	−1.7 (4)	N3'—C4'—C5'—C7'	−178.5 (2)
C2—N3—C4—O4	−176.4 (2)	C2'—N1'—C6'—O6'	178.0 (2)
C2—N3—C4—C5	1.5 (4)	C2'—N1'—C6'—C5'	−1.3 (4)
O4—C4—C5—C6	177.4 (3)	C4'—C5'—C6'—O6'	−178.0 (2)
N3—C4—C5—C6	−0.4 (4)	C7'—C5'—C6'—O6'	0.9 (4)
O4—C4—C5—C7	−1.2 (4)	C4'—C5'—C6'—N1'	1.3 (4)
N3—C4—C5—C7	−179.0 (3)	C7'—C5'—C6'—N1'	−179.8 (2)
C4—C5—C6—O6	178.2 (2)	N1'—C6'—O6'—C10'	8.6 (4)
C7—C5—C6—O6	−3.2 (4)	C6'—C5'—C7'—C9'	57.6 (4)
C4—C5—C6—N1	−0.3 (4)	C6'—C5'—C7'—C8'	−69.1 (4)
C7—C5—C6—N1	178.3 (3)	C6—C5—C7—C8	−114.9 (3)
C2—N1—C6—O6	−178.4 (2)	C4—C5—C7—C8	63.6 (4)
C2—N1—C6—C5	0.1 (4)	C4—C5—C7—C9	−62.8 (4)
N1—C6—O6—C10	−42.8 (3)	C5—C6—O6—C10	138.6 (3)
C6—C5—C7—C9	118.6 (3)	C6—O6—C10—C11	−56.1 (3)
C6'—N1'—C2'—O2'	178.4 (3)	C6—O6—C10—C12	−177.6 (2)
C6'—N1'—C2'—N3'	−0.5 (4)	C4'—C5'—C7'—C8'	109.8 (3)
O2'—C2'—N3'—C4'	−176.5 (3)	C4'—C5'—C7'—C9'	−123.5 (3)
N1'—C2'—N3'—C4'	2.4 (4)	C5'—C6'—O6'—C10'	−172.1 (3)
C2'—N3'—C4'—O4'	176.8 (2)	C6'—O6'—C10'—C11'	−91.4 (3)
C2'—N3'—C4'—C5'	−2.4 (4)	C6'—O6'—C10'—C12'	146.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4′	0.88	2.01	2.814 (3)	150
N3—H3A···O4^i	0.88	2.01	2.863 (3)	163
N1′—H1D···O2^ii	0.88	1.96	2.814 (3)	165
N3′—H3D···O4′^iii	0.88	1.97	2.853 (3)	176

Symmetry codes: (i) −x+2, −y+2, −z; (ii) −x+2, −y+1, −z; (iii) −x+1, −y+1, −z.