Crystal structure of 5-hy­droxy-5-propyl­barbituric acid

Mol­ecules of the title compound are linked via N—H...O(carbon­yl), N—H...O(hy­droxy) and O—H...O(carbon­yl) bonds into a 5-connected framework.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.037
• wR factor = 0.095
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      4.121 Check

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          4 Note
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT432_ALERT_2_G Short Inter X...Y Contact  O6     ..  C4      ..       2.87 Ang.
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          2 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   0 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
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrystalClear-SM Expert (Rigaku, 2012); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014/6 (Sheldrick, 2015b); molecular graphics: XP in SHELXTL (Sheldrick, 20088) and Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

5-Hydroxy-5-propylpyrimidine-2,4,6(1H,3H),5H)-trione

Crystal data

C7H10N2O4	F(000) = 392
Mr = 186.17	Dx = 1.473 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.7862 (8) Å	Cell parameters from 3013 reflections
b = 6.7093 (5) Å	θ = 2.4–27.5°
c = 11.7365 (6) Å	µ = 0.12 mm^−1
β = 98.632 (6)°	T = 100 K
V = 839.72 (10) Å^3	Cube, colourless
Z = 4	0.05 × 0.05 × 0.05 mm

Data collection

Rigaku Saturn724+ diffractometer	1724 independent reflections
Radiation source: Sealed Tube	1354 reflections with I > 2σ(I)
Graphite Monochromator monochromator	Rint = 0.034
Detector resolution: 28.5714 pixels mm^-1	θmax = 26.4°, θmin = 2.4°
profile data from ω–scans	h = −12→13
Absorption correction: multi-scan (CrysAlisPro; Agilent, 2014)	k = −8→8
Tmin = 0.809, Tmax = 1.000	l = −14→14
5354 measured reflections

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: mixed
wR(F^2) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0498P)^2 + 0.1441P] where P = (Fo^2 + 2Fc^2)/3
1724 reflections	(Δ/σ)max < 0.001
138 parameters	Δρmax = 0.29 e Å^−3
2 restraints	Δρmin = −0.20 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.

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

	x	y	z	Uiso*/Ueq
N1	0.75066 (12)	0.60615 (19)	0.37252 (9)	0.0154 (3)
H1	0.8189 (12)	0.536 (3)	0.3792 (16)	0.033 (5)*
O2	0.78456 (10)	0.66277 (16)	0.56534 (8)	0.0201 (3)
C2	0.72112 (13)	0.6895 (2)	0.47207 (11)	0.0147 (3)
N3	0.61584 (11)	0.80699 (19)	0.46014 (9)	0.0150 (3)
H3	0.5995 (14)	0.870 (2)	0.5200 (10)	0.020 (4)*
O4	0.47047 (9)	0.99725 (16)	0.35153 (8)	0.0180 (3)
C4	0.54700 (13)	0.8640 (2)	0.35743 (11)	0.0139 (3)
C5	0.56139 (13)	0.7360 (2)	0.25307 (11)	0.0140 (3)
O6	0.73523 (10)	0.58567 (18)	0.17883 (8)	0.0220 (3)
C6	0.68995 (13)	0.6406 (2)	0.26184 (11)	0.0153 (3)
O7	0.54144 (10)	0.85117 (16)	0.15172 (8)	0.0161 (3)
H7	0.465 (2)	0.864 (3)	0.1270 (16)	0.040 (6)*
C8	0.46287 (14)	0.5674 (2)	0.25253 (11)	0.0158 (3)
H8A	0.4849	0.4858	0.3229	0.021 (4)*
H8B	0.3799	0.6284	0.2557	0.016 (4)*
C9	0.45248 (15)	0.4312 (2)	0.14778 (13)	0.0225 (4)
H9A	0.4526	0.5128	0.0775	0.035 (5)*
H9B	0.5262	0.3417	0.1553	0.033 (5)*
C10	0.33380 (15)	0.3070 (3)	0.13545 (13)	0.0247 (4)
H10A	0.3383	0.2139	0.2003	0.034 (5)*
H10B	0.3253	0.2319	0.0631	0.036 (5)*
H10C	0.2611	0.3948	0.1350	0.044 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0131 (7)	0.0172 (7)	0.0154 (6)	0.0033 (6)	0.0002 (5)	−0.0013 (5)
O2	0.0199 (6)	0.0225 (6)	0.0159 (5)	0.0037 (5)	−0.0043 (4)	−0.0010 (4)
C2	0.0132 (8)	0.0136 (8)	0.0168 (7)	−0.0009 (6)	0.0004 (5)	0.0002 (5)
N3	0.0160 (7)	0.0173 (7)	0.0114 (6)	0.0039 (5)	0.0011 (5)	−0.0022 (5)
O4	0.0170 (6)	0.0205 (6)	0.0161 (5)	0.0058 (5)	0.0005 (4)	−0.0001 (4)
C4	0.0110 (8)	0.0155 (8)	0.0151 (7)	−0.0018 (6)	0.0016 (5)	0.0005 (5)
C5	0.0127 (8)	0.0169 (8)	0.0117 (6)	0.0010 (6)	−0.0003 (5)	0.0009 (5)
O6	0.0173 (6)	0.0323 (7)	0.0168 (5)	0.0046 (5)	0.0042 (4)	−0.0025 (5)
C6	0.0143 (8)	0.0161 (8)	0.0152 (7)	−0.0040 (6)	0.0009 (5)	−0.0003 (5)
O7	0.0143 (6)	0.0202 (6)	0.0128 (5)	−0.0006 (5)	−0.0009 (4)	0.0031 (4)
C8	0.0134 (8)	0.0178 (8)	0.0161 (6)	−0.0004 (6)	0.0021 (5)	0.0014 (6)
C9	0.0226 (9)	0.0200 (9)	0.0256 (8)	−0.0019 (7)	0.0061 (6)	−0.0065 (7)
C10	0.0262 (10)	0.0202 (9)	0.0264 (8)	−0.0030 (7)	−0.0002 (6)	0.0003 (7)

Geometric parameters (Å, º)

N1—C2	1.3754 (18)	O6—C6	1.2110 (17)
N1—C6	1.3836 (16)	O7—H7	0.84 (2)
N1—H1	0.866 (9)	C8—C9	1.5226 (19)
O2—C2	1.2141 (16)	C8—H8A	0.9900
C2—N3	1.3720 (19)	C8—H8B	0.9900
N3—C4	1.3719 (17)	C9—C10	1.516 (2)
N3—H3	0.860 (9)	C9—H9A	0.9900
O4—C4	1.2117 (17)	C9—H9B	0.9900
C4—C5	1.5228 (19)	C10—H10A	0.9800
C5—O7	1.4076 (16)	C10—H10B	0.9800
C5—C6	1.517 (2)	C10—H10C	0.9800
C5—C8	1.551 (2)
C2—N1—C6	126.31 (13)	N1—C6—C5	115.68 (12)
C2—N1—H1	116.4 (12)	C5—O7—H7	111.6 (14)
C6—N1—H1	116.8 (12)	C9—C8—C5	114.10 (12)
O2—C2—N3	121.52 (13)	C9—C8—H8A	108.7
O2—C2—N1	122.33 (14)	C5—C8—H8A	108.7
N3—C2—N1	116.15 (11)	C9—C8—H8B	108.7
C2—N3—C4	125.47 (12)	C5—C8—H8B	108.7
C2—N3—H3	117.8 (10)	H8A—C8—H8B	107.6
C4—N3—H3	115.6 (11)	C10—C9—C8	111.45 (13)
O4—C4—N3	122.02 (12)	C10—C9—H9A	109.3
O4—C4—C5	121.39 (11)	C8—C9—H9A	109.3
N3—C4—C5	116.26 (13)	C10—C9—H9B	109.3
O7—C5—C6	108.13 (11)	C8—C9—H9B	109.3
O7—C5—C4	110.43 (12)	H9A—C9—H9B	108.0
C6—C5—C4	112.70 (11)	C9—C10—H10A	109.5
O7—C5—C8	112.27 (11)	C9—C10—H10B	109.5
C6—C5—C8	108.15 (12)	H10A—C10—H10B	109.5
C4—C5—C8	105.19 (11)	C9—C10—H10C	109.5
O6—C6—N1	120.87 (14)	H10A—C10—H10C	109.5
O6—C6—C5	123.30 (12)	H10B—C10—H10C	109.5
C6—N1—C2—O2	−174.59 (14)	C2—N1—C6—C5	−16.4 (2)
C6—N1—C2—N3	4.9 (2)	O7—C5—C6—O6	−34.5 (2)
O2—C2—N3—C4	172.08 (14)	C4—C5—C6—O6	−156.87 (14)
N1—C2—N3—C4	−7.4 (2)	C8—C5—C6—O6	87.29 (17)
C2—N3—C4—O4	−165.40 (14)	O7—C5—C6—N1	149.92 (12)
C2—N3—C4—C5	21.1 (2)	C4—C5—C6—N1	27.56 (18)
O4—C4—C5—O7	35.46 (19)	C8—C5—C6—N1	−88.28 (15)
N3—C4—C5—O7	−151.01 (12)	O7—C5—C8—C9	54.47 (16)
O4—C4—C5—C6	156.51 (14)	C6—C5—C8—C9	−64.75 (14)
N3—C4—C5—C6	−29.96 (18)	C4—C5—C8—C9	174.60 (12)
O4—C4—C5—C8	−85.88 (16)	C5—C8—C9—C10	−164.80 (13)
N3—C4—C5—C8	87.64 (14)	C2—C5—C8—C9	−125.69 (11)
C2—N1—C6—O6	167.92 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O7^i	0.87 (1)	2.03 (1)	2.8683 (17)	164 (2)
N3—H3···O4^ii	0.86 (1)	2.00 (1)	2.8451 (16)	170 (2)
O7—H7···O2^iii	0.84 (2)	1.98 (2)	2.8055 (15)	169 (2)

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) −x+1, −y+2, −z+1; (iii) x−1/2, −y+3/2, z−1/2.