Self-assembly of 2-pivaloyl-6-chloro­pterin

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.

Computing details

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

Crystal data

C11H12ClN5O2	F(000) = 584
Mr = 281.71	Dx = 1.455 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.5984 (5) Å	Cell parameters from 4762 reflections
b = 9.6927 (3) Å	θ = 1.6–28.3°
c = 10.3211 (4) Å	µ = 0.30 mm^−1
β = 108.981 (1)°	T = 293 K
V = 1286.41 (8) Å^3	Slab, colourless
Z = 4	0.40 × 0.22 × 0.12 mm

Data collection

Siemens SMART CCD area detector diffractometer	3166 independent reflections
Radiation source: fine-focus sealed tube	2235 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
Detector resolution: 8.33 pixels mm^-1	θmax = 28.3°, θmin = 1.6°
ω scans	h = −18→17
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	k = −12→10
Tmin = 0.888, Tmax = 0.965	l = −12→13
8666 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)] = 0.055	Hydrogen site location: difference Fourier map
wR(F^2) = 0.157	See text
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0678P)^2 + 0.4544P] where P = (Fo^2 + 2Fc^2)/3
3166 reflections	(Δ/σ)max < 0.001
212 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.48 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.48778 (6)	0.16549 (7)	0.56281 (8)	0.0611 (3)
O1	0.29682 (17)	0.50635 (19)	0.16373 (17)	0.0563 (5)
O2	0.12292 (16)	0.8864 (2)	0.15638 (18)	0.0561 (5)
N1	0.36239 (19)	0.5055 (2)	0.6463 (2)	0.0507 (6)
N2	0.39060 (15)	0.37396 (19)	0.41777 (19)	0.0375 (4)
N3	0.26010 (15)	0.69070 (19)	0.27530 (19)	0.0344 (4)
N4	0.28587 (15)	0.69374 (19)	0.51307 (18)	0.0370 (4)
N5	0.21390 (16)	0.88258 (19)	0.3825 (2)	0.0361 (4)
C1	0.4078 (2)	0.3849 (3)	0.6550 (3)	0.0504 (7)
C2	0.42308 (18)	0.3219 (2)	0.5411 (2)	0.0395 (5)
C3	0.34195 (17)	0.4972 (2)	0.4075 (2)	0.0329 (5)
C4	0.29945 (18)	0.5599 (2)	0.2714 (2)	0.0358 (5)
C5	0.25472 (15)	0.7509 (2)	0.3922 (2)	0.0313 (4)
C6	0.33019 (17)	0.5659 (2)	0.5208 (2)	0.0349 (5)
C7	0.14683 (17)	0.9436 (2)	0.2662 (2)	0.0365 (5)
C8	0.1032 (2)	1.0845 (3)	0.2850 (3)	0.0475 (6)
C9A	0.0400 (5)	1.0619 (6)	0.3915 (7)	0.0682 (18)	0.594 (7)
H9AA	−0.0154	0.9973	0.3537	0.102*	0.594 (7)
H9AB	0.0117	1.1484	0.4077	0.102*	0.594 (7)
H9AC	0.0863	1.0266	0.4763	0.102*	0.594 (7)
C10A	0.1867 (5)	1.1842 (5)	0.3492 (8)	0.0688 (19)	0.594 (7)
H10A	0.2334	1.1455	0.4320	0.103*	0.594 (7)
H10B	0.1568	1.2675	0.3704	0.103*	0.594 (7)
H10C	0.2241	1.2047	0.2871	0.103*	0.594 (7)
C11A	0.0244 (6)	1.1321 (6)	0.1543 (6)	0.080 (2)	0.594 (7)
H11A	−0.0267	1.0612	0.1197	0.119*	0.594 (7)
H11B	0.0584	1.1514	0.0880	0.119*	0.594 (7)
H11C	−0.0089	1.2142	0.1713	0.119*	0.594 (7)
C9B	−0.0100 (7)	1.0752 (11)	0.2354 (15)	0.096 (4)	0.406 (7)
H9BA	−0.0324	1.0313	0.1472	0.144*	0.406 (7)
H9BB	−0.0392	1.1662	0.2276	0.144*	0.406 (7)
H9BC	−0.0329	1.0220	0.2986	0.144*	0.406 (7)
C10B	0.1468 (10)	1.1506 (9)	0.4207 (9)	0.077 (3)	0.406 (7)
H10D	0.2212	1.1530	0.4463	0.116*	0.406 (7)
H10E	0.1268	1.0989	0.4874	0.116*	0.406 (7)
H10F	0.1205	1.2431	0.4164	0.116*	0.406 (7)
C11B	0.1384 (12)	1.1816 (9)	0.1780 (12)	0.103 (5)	0.406 (7)
H11D	0.2128	1.1894	0.2084	0.155*	0.406 (7)
H11E	0.1082	1.2716	0.1745	0.155*	0.406 (7)
H11F	0.1148	1.1408	0.0884	0.155*	0.406 (7)
H1N5	0.225 (2)	0.918 (3)	0.460 (3)	0.045 (7)*
H1N3	0.248 (2)	0.732 (4)	0.203 (3)	0.067 (10)*
H1	0.425 (2)	0.341 (3)	0.731 (3)	0.066 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0659 (5)	0.0469 (4)	0.0690 (5)	0.0210 (3)	0.0199 (4)	0.0211 (3)
O1	0.0991 (15)	0.0432 (10)	0.0248 (9)	0.0188 (10)	0.0176 (9)	−0.0010 (7)
O2	0.0754 (13)	0.0499 (11)	0.0306 (9)	0.0191 (9)	0.0003 (8)	−0.0045 (8)
N1	0.0728 (15)	0.0518 (13)	0.0240 (10)	0.0103 (11)	0.0110 (10)	0.0078 (9)
N2	0.0458 (11)	0.0324 (10)	0.0329 (10)	0.0033 (8)	0.0110 (8)	0.0045 (7)
N3	0.0529 (11)	0.0310 (9)	0.0194 (9)	0.0042 (8)	0.0119 (8)	0.0018 (7)
N4	0.0542 (11)	0.0357 (10)	0.0225 (9)	0.0019 (8)	0.0142 (8)	−0.0003 (7)
N5	0.0527 (11)	0.0302 (9)	0.0242 (9)	0.0037 (8)	0.0111 (8)	−0.0017 (7)
C1	0.0641 (16)	0.0528 (16)	0.0302 (13)	0.0102 (13)	0.0097 (11)	0.0145 (11)
C2	0.0401 (12)	0.0359 (12)	0.0396 (13)	0.0039 (9)	0.0088 (10)	0.0086 (9)
C3	0.0405 (11)	0.0316 (11)	0.0257 (11)	−0.0012 (9)	0.0097 (9)	0.0012 (8)
C4	0.0496 (13)	0.0339 (11)	0.0240 (11)	0.0021 (9)	0.0119 (9)	0.0007 (8)
C5	0.0394 (11)	0.0307 (10)	0.0246 (10)	−0.0025 (9)	0.0114 (8)	−0.0017 (8)
C6	0.0435 (12)	0.0381 (12)	0.0212 (10)	0.0023 (9)	0.0080 (8)	0.0036 (8)
C7	0.0430 (12)	0.0333 (11)	0.0320 (12)	0.0015 (9)	0.0106 (9)	−0.0001 (9)
C8	0.0567 (15)	0.0341 (12)	0.0452 (15)	0.0084 (11)	0.0079 (11)	−0.0024 (10)
C9A	0.079 (4)	0.054 (3)	0.081 (4)	0.007 (3)	0.039 (3)	−0.008 (3)
C10A	0.074 (4)	0.037 (3)	0.088 (5)	−0.007 (2)	0.017 (3)	−0.007 (3)
C11A	0.109 (6)	0.056 (4)	0.054 (3)	0.039 (4)	0.001 (3)	0.000 (3)
C9B	0.063 (5)	0.070 (6)	0.150 (13)	0.020 (5)	0.028 (6)	−0.016 (7)
C10B	0.126 (8)	0.045 (4)	0.060 (5)	0.027 (5)	0.030 (5)	−0.005 (4)
C11B	0.192 (13)	0.050 (5)	0.102 (8)	0.038 (6)	0.095 (9)	0.035 (5)

Geometric parameters (Å, º)

Cl1—C2	1.730 (2)	N5—C5	1.382 (3)
O1—C4	1.217 (3)	C1—C2	1.399 (4)
O2—C7	1.208 (3)	C3—C6	1.400 (3)
N1—C1	1.312 (3)	C3—C4	1.466 (3)
N1—C6	1.358 (3)	C7—C8	1.526 (3)
N2—C2	1.306 (3)	C8—C9B	1.458 (10)
N2—C3	1.352 (3)	C8—C10A	1.474 (6)
N3—C5	1.363 (3)	C8—C10B	1.478 (9)
N3—C4	1.381 (3)	C8—C11A	1.497 (6)
N4—C5	1.303 (3)	C8—C9A	1.615 (6)
N4—C6	1.369 (3)	C8—C11B	1.636 (9)
N5—C7	1.382 (3)
C1—N1—C6	116.6 (2)	N5—C7—C8	116.6 (2)
C2—N2—C3	114.82 (19)	C9B—C8—C10A	140.2 (5)
C5—N3—C4	123.45 (19)	C9B—C8—C10B	114.3 (7)
C5—N4—C6	116.12 (18)	C10A—C8—C10B	43.6 (5)
C7—N5—C5	126.47 (19)	C9B—C8—C11A	48.6 (6)
N1—C1—C2	121.8 (2)	C10A—C8—C11A	115.1 (4)
N2—C2—C1	123.7 (2)	C10B—C8—C11A	132.0 (4)
N2—C2—Cl1	117.48 (19)	C9B—C8—C7	108.1 (4)
C1—C2—Cl1	118.81 (19)	C10A—C8—C7	111.7 (3)
N2—C3—C6	122.7 (2)	C10B—C8—C7	117.1 (4)
N2—C3—C4	118.17 (18)	C11A—C8—C7	110.8 (3)
C6—C3—C4	119.1 (2)	C9B—C8—C9A	59.8 (6)
O1—C4—N3	121.4 (2)	C10A—C8—C9A	106.5 (4)
O1—C4—C3	125.7 (2)	C10B—C8—C9A	63.4 (6)
N3—C4—C3	112.87 (18)	C11A—C8—C9A	105.8 (4)
N4—C5—N3	124.8 (2)	C7—C8—C9A	106.3 (3)
N4—C5—N5	117.37 (18)	C9B—C8—C11B	107.8 (8)
N3—C5—N5	117.82 (18)	C10A—C8—C11B	64.8 (6)
N1—C6—N4	116.41 (19)	C10B—C8—C11B	105.9 (7)
N1—C6—C3	120.2 (2)	C11A—C8—C11B	59.7 (6)
N4—C6—C3	123.38 (19)	C7—C8—C11B	102.6 (4)
O2—C7—N5	121.2 (2)	C9A—C8—C11B	150.9 (4)
O2—C7—C8	122.2 (2)
C6—N1—C1—C2	0.5 (4)	C5—N4—C6—N1	−179.7 (2)
C3—N2—C2—C1	1.4 (4)	C5—N4—C6—C3	−0.4 (3)
C3—N2—C2—Cl1	−179.09 (16)	N2—C3—C6—N1	−4.2 (3)
N1—C1—C2—N2	−2.8 (4)	C4—C3—C6—N1	175.4 (2)
N1—C1—C2—Cl1	177.7 (2)	N2—C3—C6—N4	176.6 (2)
C2—N2—C3—C6	2.0 (3)	C4—C3—C6—N4	−3.9 (3)
C2—N2—C3—C4	−177.6 (2)	C5—N5—C7—O2	−5.2 (4)
C5—N3—C4—O1	175.2 (2)	C5—N5—C7—C8	173.5 (2)
C5—N3—C4—C3	−4.4 (3)	O2—C7—C8—C9B	55.7 (7)
N2—C3—C4—O1	5.9 (4)	N5—C7—C8—C9B	−123.0 (7)
C6—C3—C4—O1	−173.7 (2)	O2—C7—C8—C10A	−125.7 (4)
N2—C3—C4—N3	−174.5 (2)	N5—C7—C8—C10A	55.6 (4)
C6—C3—C4—N3	5.9 (3)	O2—C7—C8—C10B	−173.6 (6)
C6—N4—C5—N3	2.4 (3)	N5—C7—C8—C10B	7.8 (7)
C6—N4—C5—N5	−177.18 (19)	O2—C7—C8—C11A	4.0 (5)
C4—N3—C5—N4	0.3 (3)	N5—C7—C8—C11A	−174.7 (4)
C4—N3—C5—N5	179.8 (2)	O2—C7—C8—C9A	118.5 (3)
C7—N5—C5—N4	−156.9 (2)	N5—C7—C8—C9A	−60.2 (4)
C7—N5—C5—N3	23.5 (3)	O2—C7—C8—C11B	−58.1 (6)
C1—N1—C6—N4	−178.0 (2)	N5—C7—C8—C11B	123.3 (6)
C1—N1—C6—C3	2.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···N4^i	0.82 (3)	2.30 (3)	3.053 (3)	154 (3)
N5—H1N5···O1^ii	0.84 (3)	2.14 (3)	2.954 (3)	164 (3)

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