[(5-Fluoro-2,4-dioxo-1,2,3,4-tetra­hydro­pyrimidin-1-yl)acetamido]acetic acid–4,4′-bipyridine (2/1)

In the title complex, C₈H₈FN₃O₅·0.5C₁₀H₈N₂, one [(5-fluoro-2,4-dioxo-1,2,3,4-tetra­hydro­pyrimidin-1-yl)acetamido]acetic acid mol­ecule and one half 4,4′-bipyridine mol­ecule comprise the asymmetric unit. The 4,4′-bipyridine molecule has inversion symmetry. All bond lengths and angles in both molecules show normal values. An extensive three-dimensional network of inter­molecular N—H...O and O—H...N hydrogen bonds stabilizes the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.083
• wR factor = 0.226
• Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       3.03
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.

[(5-Fluoro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)acetamido]acetic acid–4,4'-bipyridine (2/1)

Crystal data

C8H8FN3O5·0.5C10H8N2	F(000) = 1336
Mr = 323.27	Dx = 1.525 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2253 reflections
a = 31.969 (2) Å	θ = 2.6–24.6°
b = 11.264 (9) Å	µ = 0.13 mm^−1
c = 7.863 (6) Å	T = 298 K
β = 96.071 (2)°	Rod, colourless
V = 2816 (3) Å^3	0.34 × 0.26 × 0.14 mm
Z = 8

Data collection

Bruker APEX area-detector diffractometer	2543 independent reflections
Radiation source: fine-focus sealed tube	2337 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 25.2°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −38→38
Tmin = 0.958, Tmax = 0.979	k = −13→13
7271 measured reflections	l = −9→7

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)] = 0.083	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.226	H-atom parameters constrained
S = 1.31	w = 1/[σ^2(Fo^2) + (0.095P)^2 + 5.058P] where P = (Fo^2 + 2Fc^2)/3
2543 reflections	(Δ/σ)max < 0.001
209 parameters	Δρmax = 0.47 e Å^−3
0 restraints	Δρmin = −0.33 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
F1	0.35442 (8)	0.9066 (2)	0.0950 (4)	0.0594 (8)
O1	0.06748 (9)	1.0050 (2)	0.1352 (5)	0.0617 (9)
H1	0.0590	0.9380	0.1098	0.093*
O2	0.12775 (9)	0.9112 (2)	0.2036 (5)	0.0589 (9)
O3	0.19596 (8)	1.1022 (3)	0.0978 (3)	0.0437 (7)
O4	0.26827 (10)	1.2840 (2)	0.2722 (4)	0.0540 (8)
O5	0.37771 (8)	1.1353 (3)	0.0160 (4)	0.0514 (8)
N1	0.16580 (9)	1.1125 (3)	0.3432 (4)	0.0359 (7)
H1A	0.1702	1.1186	0.4526	0.043*
N2	0.27627 (9)	1.0843 (2)	0.2696 (4)	0.0288 (7)
N3	0.32256 (10)	1.2063 (3)	0.1448 (5)	0.0423 (8)
H3	0.3299	1.2771	0.1195	0.051*
N4	0.03821 (10)	0.7934 (3)	0.0582 (5)	0.0497 (9)
C1	0.10664 (11)	1.0000 (3)	0.1984 (5)	0.0379 (9)
C2	0.12358 (11)	1.1192 (3)	0.2614 (5)	0.0377 (9)
H2A	0.1229	1.1734	0.1652	0.045*
H2B	0.1055	1.1512	0.3416	0.045*
C3	0.19847 (10)	1.0972 (3)	0.2523 (4)	0.0282 (7)
C4	0.23933 (11)	1.0697 (3)	0.3624 (4)	0.0323 (8)
H4A	0.2419	1.1219	0.4611	0.039*
H4B	0.2384	0.9887	0.4036	0.039*
C5	0.28752 (11)	1.1978 (3)	0.2314 (5)	0.0348 (8)
C6	0.34757 (10)	1.1159 (3)	0.0929 (5)	0.0342 (8)
C7	0.33266 (11)	1.0015 (3)	0.1413 (5)	0.0333 (8)
C8	0.29878 (11)	0.9880 (3)	0.2229 (4)	0.0320 (8)
H8	0.2901	0.9120	0.2491	0.038*
C9	−0.00173 (14)	0.7712 (4)	0.0105 (9)	0.0726 (17)
H9	−0.0200	0.8351	−0.0084	0.087*
C10	−0.01785 (13)	0.6589 (4)	−0.0127 (8)	0.0698 (16)
H10	−0.0464	0.6484	−0.0454	0.084*
C11	0.00799 (11)	0.5621 (3)	0.0120 (5)	0.0389 (9)
C12	0.05005 (13)	0.5850 (4)	0.0604 (7)	0.0546 (12)
H12	0.0691	0.5228	0.0791	0.065*
C13	0.06338 (13)	0.7004 (4)	0.0807 (7)	0.0555 (12)
H13	0.0918	0.7139	0.1122	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0612 (16)	0.0341 (13)	0.087 (2)	0.0169 (11)	0.0268 (14)	−0.0047 (12)
O1	0.0356 (15)	0.0322 (15)	0.113 (3)	0.0045 (12)	−0.0132 (16)	−0.0024 (17)
O2	0.0424 (16)	0.0329 (16)	0.098 (3)	0.0093 (12)	−0.0090 (16)	0.0009 (15)
O3	0.0433 (15)	0.0609 (18)	0.0276 (13)	0.0139 (13)	0.0067 (11)	0.0026 (12)
O4	0.0671 (19)	0.0262 (14)	0.075 (2)	0.0100 (13)	0.0397 (17)	0.0049 (13)
O5	0.0373 (15)	0.0483 (17)	0.072 (2)	−0.0015 (12)	0.0239 (14)	−0.0019 (14)
N1	0.0341 (16)	0.0418 (17)	0.0329 (16)	−0.0010 (13)	0.0086 (12)	−0.0031 (13)
N2	0.0296 (14)	0.0265 (14)	0.0308 (15)	0.0005 (11)	0.0056 (11)	0.0027 (11)
N3	0.0448 (18)	0.0217 (15)	0.064 (2)	−0.0024 (13)	0.0246 (16)	0.0013 (14)
N4	0.0383 (18)	0.0353 (18)	0.075 (3)	−0.0015 (14)	0.0023 (17)	0.0014 (16)
C1	0.0319 (18)	0.0293 (19)	0.053 (2)	0.0063 (15)	0.0061 (16)	0.0079 (16)
C2	0.0303 (18)	0.0350 (19)	0.049 (2)	0.0025 (15)	0.0110 (16)	0.0012 (17)
C3	0.0343 (18)	0.0202 (16)	0.0306 (18)	0.0027 (13)	0.0068 (14)	−0.0020 (13)
C4	0.0361 (18)	0.0331 (18)	0.0286 (18)	−0.0022 (15)	0.0075 (14)	0.0042 (14)
C5	0.0397 (19)	0.0242 (17)	0.043 (2)	0.0029 (14)	0.0133 (16)	0.0007 (15)
C6	0.0264 (17)	0.0338 (19)	0.043 (2)	−0.0015 (14)	0.0039 (15)	−0.0026 (15)
C7	0.0307 (17)	0.0267 (17)	0.043 (2)	0.0079 (14)	0.0034 (15)	−0.0063 (15)
C8	0.0365 (19)	0.0226 (16)	0.0357 (19)	−0.0006 (14)	−0.0018 (15)	0.0032 (14)
C9	0.038 (2)	0.034 (2)	0.142 (5)	0.0059 (18)	−0.009 (3)	−0.001 (3)
C10	0.028 (2)	0.042 (3)	0.135 (5)	0.0019 (18)	−0.009 (3)	−0.002 (3)
C11	0.0307 (18)	0.036 (2)	0.051 (2)	0.0004 (15)	0.0089 (16)	0.0020 (16)
C12	0.033 (2)	0.036 (2)	0.093 (4)	0.0022 (17)	0.000 (2)	0.003 (2)
C13	0.032 (2)	0.043 (2)	0.089 (4)	−0.0058 (17)	−0.002 (2)	0.002 (2)

Geometric parameters (Å, º)

F1—C7	1.346 (4)	C1—C2	1.511 (5)
O1—C1	1.299 (4)	C2—H2A	0.9700
O1—H1	0.8200	C2—H2B	0.9700
O2—C1	1.205 (4)	C3—C4	1.520 (5)
O3—C3	1.210 (4)	C4—H4A	0.9700
O4—C5	1.211 (4)	C4—H4B	0.9700
O5—C6	1.210 (4)	C6—C7	1.439 (5)
N1—C3	1.337 (4)	C7—C8	1.325 (5)
N1—C2	1.434 (5)	C8—H8	0.9300
N1—H1A	0.8600	C9—C10	1.370 (7)
N2—C5	1.370 (4)	C9—H9	0.9300
N2—C8	1.372 (4)	C10—C11	1.369 (6)
N2—C4	1.462 (4)	C10—H10	0.9300
N3—C5	1.375 (5)	C11—C12	1.383 (5)
N3—C6	1.383 (5)	C11—C11^i	1.494 (8)
N3—H3	0.8600	C12—C13	1.371 (6)
N4—C9	1.316 (5)	C12—H12	0.9300
N4—C13	1.322 (5)	C13—H13	0.9300
C1—O1—H1	109.5	H4A—C4—H4B	107.8
C3—N1—C2	121.2 (3)	O4—C5—N2	122.6 (3)
C3—N1—H1A	119.4	O4—C5—N3	122.6 (3)
C2—N1—H1A	119.4	N2—C5—N3	114.9 (3)
C5—N2—C8	121.4 (3)	O5—C6—N3	122.0 (3)
C5—N2—C4	117.3 (3)	O5—C6—C7	126.7 (3)
C8—N2—C4	121.3 (3)	N3—C6—C7	111.3 (3)
C5—N3—C6	128.4 (3)	C8—C7—F1	120.8 (3)
C5—N3—H3	115.8	C8—C7—C6	122.8 (3)
C6—N3—H3	115.8	F1—C7—C6	116.4 (3)
C9—N4—C13	116.5 (4)	C7—C8—N2	121.2 (3)
O2—C1—O1	124.3 (4)	C7—C8—H8	119.4
O2—C1—C2	123.1 (3)	N2—C8—H8	119.4
O1—C1—C2	112.6 (3)	N4—C9—C10	123.6 (4)
N1—C2—C1	112.9 (3)	N4—C9—H9	118.2
N1—C2—H2A	109.0	C10—C9—H9	118.2
C1—C2—H2A	109.0	C11—C10—C9	120.2 (4)
N1—C2—H2B	109.0	C11—C10—H10	119.9
C1—C2—H2B	109.0	C9—C10—H10	119.9
H2A—C2—H2B	107.8	C10—C11—C12	116.4 (4)
O3—C3—N1	123.9 (3)	C10—C11—C11^i	122.3 (4)
O3—C3—C4	122.8 (3)	C12—C11—C11^i	121.3 (4)
N1—C3—C4	113.3 (3)	C13—C12—C11	119.4 (4)
N2—C4—C3	112.6 (3)	C13—C12—H12	120.3
N2—C4—H4A	109.1	C11—C12—H12	120.3
C3—C4—H4A	109.1	N4—C13—C12	123.9 (4)
N2—C4—H4B	109.1	N4—C13—H13	118.0
C3—C4—H4B	109.1	C12—C13—H13	118.0
C3—N1—C2—C1	74.0 (4)	O5—C6—C7—C8	−178.7 (4)
O2—C1—C2—N1	−6.0 (6)	N3—C6—C7—C8	0.9 (5)
O1—C1—C2—N1	175.5 (3)	O5—C6—C7—F1	−0.5 (6)
C2—N1—C3—O3	9.3 (5)	N3—C6—C7—F1	179.2 (3)
C2—N1—C3—C4	−169.3 (3)	F1—C7—C8—N2	−179.6 (3)
C5—N2—C4—C3	71.4 (4)	C6—C7—C8—N2	−1.4 (5)
C8—N2—C4—C3	−108.6 (3)	C5—N2—C8—C7	1.0 (5)
O3—C3—C4—N2	16.6 (5)	C4—N2—C8—C7	−178.9 (3)
N1—C3—C4—N2	−164.8 (3)	C13—N4—C9—C10	1.3 (9)
C8—N2—C5—O4	−179.6 (4)	N4—C9—C10—C11	−0.7 (10)
C4—N2—C5—O4	0.3 (5)	C9—C10—C11—C12	0.0 (8)
C8—N2—C5—N3	−0.2 (5)	C9—C10—C11—C11^i	−179.9 (6)
C4—N2—C5—N3	179.8 (3)	C10—C11—C12—C13	0.0 (8)
C6—N3—C5—O4	179.1 (4)	C11^i—C11—C12—C13	179.9 (5)
C6—N3—C5—N2	−0.3 (6)	C9—N4—C13—C12	−1.3 (8)
C5—N3—C6—O5	179.6 (4)	C11—C12—C13—N4	0.7 (8)
C5—N3—C6—C7	0.0 (6)

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N4	0.82	1.79	2.609 (5)	177
N1—H1A···O2^ii	0.86	2.53	3.212 (5)	137
N3—H3···O3^iii	0.86	2.27	2.899 (4)	130
N3—H3···O2^iv	0.86	2.38	2.978 (4)	127

Symmetry codes: (ii) x, −y+2, z+1/2; (iii) −x+1/2, −y+5/2, −z; (iv) −x+1/2, y+1/2, −z+1/2.