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In the title compound, N-(6-chloro-4-oxo-3,4-di­hydro­pteridin-2-yl)­-2,2-di­methyl­propan­amide, C11H12ClN5O2, the rings in the pterin moiety are planar. The amide carbonyl O atom is in syn-periplanar conformation while the C-N-C-C propanamide linkage is antiperiplanar. The N-H...N and N-H...O intermolecular hydrogen bonds transform the mol­ecules into infinite chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100004121/sk1368sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100004121/sk1368Isup2.hkl
Contains datablock I

CCDC reference: 146070

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Self-assembly of 2-pivaloylchloropterin top
Crystal data top
C11H12ClN5O2F(000) = 584
Mr = 281.71Dx = 1.455 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.5984 (5) ÅCell parameters from 4762 reflections
b = 9.6927 (3) Åθ = 1.6–28.3°
c = 10.3211 (4) ŵ = 0.30 mm1
β = 108.981 (1)°T = 293 K
V = 1286.41 (8) Å3Slab, colourless
Z = 40.40 × 0.22 × 0.12 mm
Data collection top
Siemens SMART CCD area detector
diffractometer
3166 independent reflections
Radiation source: fine-focus sealed tube2235 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.053
Detector resolution: 8.33 pixels mm-1θmax = 28.3°, θmin = 1.6°
ω scansh = 1817
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 1210
Tmin = 0.888, Tmax = 0.965l = 1213
8666 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: difference Fourier map
wR(F2) = 0.157See text
S = 1.07 w = 1/[σ2(Fo2) + (0.0678P)2 + 0.4544P]
where P = (Fo2 + 2Fc2)/3
3166 reflections(Δ/σ)max < 0.001
212 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.48 e Å3
Special details top

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different φ angle (0, 88 and 180°) for the crystal and each exposure of 30 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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.

The structure was solved by direct methods and refined by full-matrix least-squares techniques.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.48778 (6)0.16549 (7)0.56281 (8)0.0611 (3)
O10.29682 (17)0.50635 (19)0.16373 (17)0.0563 (5)
O20.12292 (16)0.8864 (2)0.15638 (18)0.0561 (5)
N10.36239 (19)0.5055 (2)0.6463 (2)0.0507 (6)
N20.39060 (15)0.37396 (19)0.41777 (19)0.0375 (4)
N30.26010 (15)0.69070 (19)0.27530 (19)0.0344 (4)
N40.28587 (15)0.69374 (19)0.51307 (18)0.0370 (4)
N50.21390 (16)0.88258 (19)0.3825 (2)0.0361 (4)
C10.4078 (2)0.3849 (3)0.6550 (3)0.0504 (7)
C20.42308 (18)0.3219 (2)0.5411 (2)0.0395 (5)
C30.34195 (17)0.4972 (2)0.4075 (2)0.0329 (5)
C40.29945 (18)0.5599 (2)0.2714 (2)0.0358 (5)
C50.25472 (15)0.7509 (2)0.3922 (2)0.0313 (4)
C60.33019 (17)0.5659 (2)0.5208 (2)0.0349 (5)
C70.14683 (17)0.9436 (2)0.2662 (2)0.0365 (5)
C80.1032 (2)1.0845 (3)0.2850 (3)0.0475 (6)
C9A0.0400 (5)1.0619 (6)0.3915 (7)0.0682 (18)0.594 (7)
H9AA0.01540.99730.35370.102*0.594 (7)
H9AB0.01171.14840.40770.102*0.594 (7)
H9AC0.08631.02660.47630.102*0.594 (7)
C10A0.1867 (5)1.1842 (5)0.3492 (8)0.0688 (19)0.594 (7)
H10A0.23341.14550.43200.103*0.594 (7)
H10B0.15681.26750.37040.103*0.594 (7)
H10C0.22411.20470.28710.103*0.594 (7)
C11A0.0244 (6)1.1321 (6)0.1543 (6)0.080 (2)0.594 (7)
H11A0.02671.06120.11970.119*0.594 (7)
H11B0.05841.15140.08800.119*0.594 (7)
H11C0.00891.21420.17130.119*0.594 (7)
C9B0.0100 (7)1.0752 (11)0.2354 (15)0.096 (4)0.406 (7)
H9BA0.03241.03130.14720.144*0.406 (7)
H9BB0.03921.16620.22760.144*0.406 (7)
H9BC0.03291.02200.29860.144*0.406 (7)
C10B0.1468 (10)1.1506 (9)0.4207 (9)0.077 (3)0.406 (7)
H10D0.22121.15300.44630.116*0.406 (7)
H10E0.12681.09890.48740.116*0.406 (7)
H10F0.12051.24310.41640.116*0.406 (7)
C11B0.1384 (12)1.1816 (9)0.1780 (12)0.103 (5)0.406 (7)
H11D0.21281.18940.20840.155*0.406 (7)
H11E0.10821.27160.17450.155*0.406 (7)
H11F0.11481.14080.08840.155*0.406 (7)
H1N50.225 (2)0.918 (3)0.460 (3)0.045 (7)*
H1N30.248 (2)0.732 (4)0.203 (3)0.067 (10)*
H10.425 (2)0.341 (3)0.731 (3)0.066 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0659 (5)0.0469 (4)0.0690 (5)0.0210 (3)0.0199 (4)0.0211 (3)
O10.0991 (15)0.0432 (10)0.0248 (9)0.0188 (10)0.0176 (9)0.0010 (7)
O20.0754 (13)0.0499 (11)0.0306 (9)0.0191 (9)0.0003 (8)0.0045 (8)
N10.0728 (15)0.0518 (13)0.0240 (10)0.0103 (11)0.0110 (10)0.0078 (9)
N20.0458 (11)0.0324 (10)0.0329 (10)0.0033 (8)0.0110 (8)0.0045 (7)
N30.0529 (11)0.0310 (9)0.0194 (9)0.0042 (8)0.0119 (8)0.0018 (7)
N40.0542 (11)0.0357 (10)0.0225 (9)0.0019 (8)0.0142 (8)0.0003 (7)
N50.0527 (11)0.0302 (9)0.0242 (9)0.0037 (8)0.0111 (8)0.0017 (7)
C10.0641 (16)0.0528 (16)0.0302 (13)0.0102 (13)0.0097 (11)0.0145 (11)
C20.0401 (12)0.0359 (12)0.0396 (13)0.0039 (9)0.0088 (10)0.0086 (9)
C30.0405 (11)0.0316 (11)0.0257 (11)0.0012 (9)0.0097 (9)0.0012 (8)
C40.0496 (13)0.0339 (11)0.0240 (11)0.0021 (9)0.0119 (9)0.0007 (8)
C50.0394 (11)0.0307 (10)0.0246 (10)0.0025 (9)0.0114 (8)0.0017 (8)
C60.0435 (12)0.0381 (12)0.0212 (10)0.0023 (9)0.0080 (8)0.0036 (8)
C70.0430 (12)0.0333 (11)0.0320 (12)0.0015 (9)0.0106 (9)0.0001 (9)
C80.0567 (15)0.0341 (12)0.0452 (15)0.0084 (11)0.0079 (11)0.0024 (10)
C9A0.079 (4)0.054 (3)0.081 (4)0.007 (3)0.039 (3)0.008 (3)
C10A0.074 (4)0.037 (3)0.088 (5)0.007 (2)0.017 (3)0.007 (3)
C11A0.109 (6)0.056 (4)0.054 (3)0.039 (4)0.001 (3)0.000 (3)
C9B0.063 (5)0.070 (6)0.150 (13)0.020 (5)0.028 (6)0.016 (7)
C10B0.126 (8)0.045 (4)0.060 (5)0.027 (5)0.030 (5)0.005 (4)
C11B0.192 (13)0.050 (5)0.102 (8)0.038 (6)0.095 (9)0.035 (5)
Geometric parameters (Å, º) top
Cl1—C21.730 (2)N5—C51.382 (3)
O1—C41.217 (3)C1—C21.399 (4)
O2—C71.208 (3)C3—C61.400 (3)
N1—C11.312 (3)C3—C41.466 (3)
N1—C61.358 (3)C7—C81.526 (3)
N2—C21.306 (3)C8—C9B1.458 (10)
N2—C31.352 (3)C8—C10A1.474 (6)
N3—C51.363 (3)C8—C10B1.478 (9)
N3—C41.381 (3)C8—C11A1.497 (6)
N4—C51.303 (3)C8—C9A1.615 (6)
N4—C61.369 (3)C8—C11B1.636 (9)
N5—C71.382 (3)
C1—N1—C6116.6 (2)N5—C7—C8116.6 (2)
C2—N2—C3114.82 (19)C9B—C8—C10A140.2 (5)
C5—N3—C4123.45 (19)C9B—C8—C10B114.3 (7)
C5—N4—C6116.12 (18)C10A—C8—C10B43.6 (5)
C7—N5—C5126.47 (19)C9B—C8—C11A48.6 (6)
N1—C1—C2121.8 (2)C10A—C8—C11A115.1 (4)
N2—C2—C1123.7 (2)C10B—C8—C11A132.0 (4)
N2—C2—Cl1117.48 (19)C9B—C8—C7108.1 (4)
C1—C2—Cl1118.81 (19)C10A—C8—C7111.7 (3)
N2—C3—C6122.7 (2)C10B—C8—C7117.1 (4)
N2—C3—C4118.17 (18)C11A—C8—C7110.8 (3)
C6—C3—C4119.1 (2)C9B—C8—C9A59.8 (6)
O1—C4—N3121.4 (2)C10A—C8—C9A106.5 (4)
O1—C4—C3125.7 (2)C10B—C8—C9A63.4 (6)
N3—C4—C3112.87 (18)C11A—C8—C9A105.8 (4)
N4—C5—N3124.8 (2)C7—C8—C9A106.3 (3)
N4—C5—N5117.37 (18)C9B—C8—C11B107.8 (8)
N3—C5—N5117.82 (18)C10A—C8—C11B64.8 (6)
N1—C6—N4116.41 (19)C10B—C8—C11B105.9 (7)
N1—C6—C3120.2 (2)C11A—C8—C11B59.7 (6)
N4—C6—C3123.38 (19)C7—C8—C11B102.6 (4)
O2—C7—N5121.2 (2)C9A—C8—C11B150.9 (4)
O2—C7—C8122.2 (2)
C6—N1—C1—C20.5 (4)C5—N4—C6—N1179.7 (2)
C3—N2—C2—C11.4 (4)C5—N4—C6—C30.4 (3)
C3—N2—C2—Cl1179.09 (16)N2—C3—C6—N14.2 (3)
N1—C1—C2—N22.8 (4)C4—C3—C6—N1175.4 (2)
N1—C1—C2—Cl1177.7 (2)N2—C3—C6—N4176.6 (2)
C2—N2—C3—C62.0 (3)C4—C3—C6—N43.9 (3)
C2—N2—C3—C4177.6 (2)C5—N5—C7—O25.2 (4)
C5—N3—C4—O1175.2 (2)C5—N5—C7—C8173.5 (2)
C5—N3—C4—C34.4 (3)O2—C7—C8—C9B55.7 (7)
N2—C3—C4—O15.9 (4)N5—C7—C8—C9B123.0 (7)
C6—C3—C4—O1173.7 (2)O2—C7—C8—C10A125.7 (4)
N2—C3—C4—N3174.5 (2)N5—C7—C8—C10A55.6 (4)
C6—C3—C4—N35.9 (3)O2—C7—C8—C10B173.6 (6)
C6—N4—C5—N32.4 (3)N5—C7—C8—C10B7.8 (7)
C6—N4—C5—N5177.18 (19)O2—C7—C8—C11A4.0 (5)
C4—N3—C5—N40.3 (3)N5—C7—C8—C11A174.7 (4)
C4—N3—C5—N5179.8 (2)O2—C7—C8—C9A118.5 (3)
C7—N5—C5—N4156.9 (2)N5—C7—C8—C9A60.2 (4)
C7—N5—C5—N323.5 (3)O2—C7—C8—C11B58.1 (6)
C1—N1—C6—N4178.0 (2)N5—C7—C8—C11B123.3 (6)
C1—N1—C6—C32.7 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H1N3···N4i0.82 (3)2.30 (3)3.053 (3)154 (3)
N5—H1N5···O1ii0.84 (3)2.14 (3)2.954 (3)164 (3)
Symmetry codes: (i) x, y+3/2, z1/2; (ii) x, y+3/2, z+1/2.
 

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