N-[2-(2,2-Di­methyl­propanamido)­pyrimidin-4-yl]-2,2-di­methyl­propanamide n-hexane 0.25-solvate hemihydrate

Ośmiałowski, B.; Valkonen, A.; Chęcińska, L.

doi:10.1107/S160053681302713X

organic compounds

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ISSN: 2056-9890

Volume 69| Part 11| November 2013| Pages o1617-o1618

doi:10.1107/S160053681302713X

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N-[2-(2,2-Dimethylpropanamido)pyrimidin-4-yl]-2,2-dimethylpropanamide n-hexane 0.25-solvate hemihydrate

Borys Ośmiałowski,^a Arto Valkonen ^b and Lilianna Chęcińska ^c ^*

^aFaculty of Technology and Chemical Engineering, University of Technology and Life Sciences, Seminaryjna 3, PL-85-326 Bydgoszcz, Poland, ^bDepartment of Chemistrycv5431, University of Jyväskylä, P.O. Box 35, FI-40014 Jyväskylä, Finland, and ^cStructural Chemistry and Crystallography Group, University of Lodz, Pomorska 163/165, PL-90-236 Łódź, Poland
^*Correspondence e-mail: lilach@uni.lodz.pl

(Received 28 September 2013; accepted 2 October 2013; online 5 October 2013)

The asymmetric unit of the title compound, C₁₄H₂₂N₄O₂·0.25C₆H₁₄·0.5H₂O, contains two independent molecules of 2,4-bis(pivaloylamino)pyrimidine (M) with similar conformations, one water molecule and one-half n-hexane solvent molecule situated on an inversion center. In one independent M molecule, one of the two tert-butyl groups is rotationally disordered between two orientations in a 3:2 ratio. The n-hexane solvent molecule is disordered between two conformations in the same ratio. The water molecule bridges two independent M molecules via O—H⋯O, N—H⋯O and O—H⋯N hydrogen bonds into a 2M·H₂O unit, and these units are further linked by N—H⋯N hydrogen bonds into chains running in the [010] direction. Weak C—H⋯O interactions are observed between the adjacent chains.

CCDC reference: 964448

Related literature

For the related structures of 2,4-bis(acyloamino)pyrimidines in the solid state and in solution, see: Ośmiałowski et al. (2012 ). For the related structures of 2,6-bis(acyloamino)pyridines, see: Ośmiałowski et al. (2010 ); Crane (2003 ).

Experimental

Crystal data

2C₁₄H₂₂N₄O₂·0.5C₆H₁₄·H₂O
M_r = 617.81
Triclinic, $[P \overline 1]$
a = 10.6055 (5) Å
b = 12.2181 (6) Å
c = 14.9774 (7) Å
α = 88.060 (3)°
β = 73.093 (4)°
γ = 74.179 (3)°
V = 1784.36 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 123 K
0.30 × 0.05 × 0.04 mm

Data collection

Bruker–Nonius KappaCCD diffractometer with an APEXII detector
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.977, T_max = 0.997
21621 measured reflections
6422 independent reflections
3597 reflections with I > 2σ(I)
R_int = 0.100

Refinement

R[F² > 2σ(F²)] = 0.079
wR(F²) = 0.164
S = 1.04
6422 reflections
451 parameters
101 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O8A	0.84 (2)	2.08 (2)	2.910 (3)	167 (4)
O1—H1A⋯N1A	0.84 (2)	2.51 (4)	2.958 (4)	115 (3)
O1—H1B⋯O8	0.83 (2)	2.13 (2)	2.943 (3)	168 (4)
O1—H1B⋯N1	0.83 (2)	2.48 (4)	2.931 (4)	115 (3)
N7—H7⋯N3Aⁱ	0.88 (2)	2.32 (2)	3.144 (4)	156 (3)
N13—H13⋯O1	0.87 (2)	2.02 (2)	2.864 (4)	162 (4)
N7A—H7A⋯N3ⁱⁱ	0.87 (2)	2.16 (2)	2.958 (4)	152 (3)
N13A—H13A⋯O1	0.89 (2)	2.02 (2)	2.882 (4)	164 (4)
C5—H5⋯O14ⁱⁱⁱ	0.95	2.37	3.205 (5)	147
Symmetry codes: (i) x, y+1, z; (ii) x, y-1, z; (iii) -x+1, -y+1, -z+1.

Data collection: COLLECT (Bruker, 2008 ); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ); data reduction: DENZO-SMN; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL2013 and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 964448

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681302713X/cv5431sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681302713X/cv5431Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681302713X/cv5431Isup3.cml

checkCIF report

Comment top

The 2,4-bis(pivaloylamino)pyrimidine is able to form various rotamers in solution (Ośmiałowski et al., 2012). The high flexibility of this molecule with respect to the related pyridine derivatives is caused by the presence of two nitrogen atoms within the aromatic ring. This was confirmed by studies of association of such derivatives with various supramolecular counterparts (Ośmiałowski et al., 2010; 2012). In the crystal structure of the related pyridine derivative (2,6-bis(pivaloylamino)pyridine) a weak N—H···O═C interaction was found, which further links the molecules into chain motif (Crane, 2003).

The 2,4-bis(pivaloylamino)pyrimidine was crystallized from n-hexane as hemisolvate monohydrate. In the asymmetric unit there are two independent molecules of the title compound (Figure 1). Water molecule interacts with these molecules via O—H···O, N—H···O and O—H···N intermolecular hydrogen bonds (Table 1) thereby joins them into hydrogen-bonded dimer (Figure 2). It is worth mentioning that water molecule incorporated between two subjected molecules forces those to adopt the Z,E,Z,Z conformation (Ośmiałowski et al., 2012), in which the electron repulsion between heterocyclic nitrogen atoms (N1, N1A) and carbonyl oxygen atoms (O8, O8A) are observed.

Furthermore, each independent molecule forms an intermolecular N—H···N hydrogen bond (Table 1), thus producing infinite chain of dimers running parallel to the [010] direction. Two centrosymmetrically related chains interact each other via weak C—H···O interactions (Table 1).

The partially disordered n-hexane solvent molecule lies on the inversion centre. In the crystal lattice it is surrounded by the terminal t-butyl groups. This arrangement precludes any significant intermolecular interactions with other molecules in crystal.

Related literature top

For the related structures of 2,4-bis(acyloamino)pyrimidines in the solid state and in solution, see: Ośmiałowski et al. (2012). For the related structures of 2,6-bis(acyloamino)pyridines, see: Ośmiałowski et al. (2010); Crane (2003).

Experimental top

The title compound was synthesized according to the method of Ośmiałowski et al. (2012). Crystals suitable for X-ray measurements were obtained by crystallization from n-hexane.

Computing details top

Data collection: COLLECT (Bruker, 2008); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. Two independent molecules M in (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms. Only the major component of disordered t-butyl group is shown. Water and hexane solvent molecules are omitted for clarity.
	Fig. 2. Part of the crystal structure of (I) showing the intermolecular hydrogen-bonds [symmetry codes: (i) x, 1 + y, z; (ii) x, y - 1, z; (iii) 1 - x, 1 - y,1 - z]. Hexane solvent molecule, the minor components of disordered t-butyl group and (C)—H atoms are omitted for clarity.

N-[2-(2,2-Dimethylpropanamido)pyrimidin-4-yl]-2,2-dimethylpropanamide n-hexane 0.25-solvate hemihydrate top

Crystal data top

2C₁₄H₂₂N₄O₂·0.5C₆H₁₄·H₂O	Z = 2
M_r = 617.81	F(000) = 670
Triclinic, P1	D_x = 1.150 Mg m⁻³
a = 10.6055 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.2181 (6) Å	Cell parameters from 7150 reflections
c = 14.9774 (7) Å	θ = 0.4–28.3°
α = 88.060 (3)°	µ = 0.08 mm⁻¹
β = 73.093 (4)°	T = 123 K
γ = 74.179 (3)°	Needle, colourless
V = 1784.36 (16) Å³	0.30 × 0.05 × 0.04 mm

Data collection top

Bruker–Nonius KappaCCD with APEXII detector diffractometer	6422 independent reflections
Radiation source: fine-focus sealed tube	3597 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.100
Detector resolution: 9 pixels mm^-1	θ_max = 25.3°, θ_min = 2.3°
ϕ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	k = −14→14
T_min = 0.977, T_max = 0.997	l = −16→17
21621 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.079	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0128P)² + 3.1862P] where P = (F_o² + 2F_c²)/3
6422 reflections	(Δ/σ)_max = 0.001
451 parameters	Δρ_max = 0.35 e Å⁻³
101 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

2C₁₄H₂₂N₄O₂·0.5C₆H₁₄·H₂O	γ = 74.179 (3)°
M_r = 617.81	V = 1784.36 (16) Å³
Triclinic, P1	Z = 2
a = 10.6055 (5) Å	Mo Kα radiation
b = 12.2181 (6) Å	µ = 0.08 mm⁻¹
c = 14.9774 (7) Å	T = 123 K
α = 88.060 (3)°	0.30 × 0.05 × 0.04 mm
β = 73.093 (4)°

Data collection top

Bruker–Nonius KappaCCD with APEXII detector diffractometer	6422 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	3597 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.997	R_int = 0.100
21621 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.079	101 restraints
wR(F²) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.35 e Å⁻³
6422 reflections	Δρ_min = −0.24 e Å⁻³
451 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O8	0.3412 (3)	0.46261 (19)	0.05984 (17)	0.0307 (6)
O14	0.4845 (3)	0.3749 (2)	0.46471 (17)	0.0358 (7)
N1	0.3512 (3)	0.5088 (2)	0.2372 (2)	0.0233 (7)
N3	0.3818 (3)	0.6952 (2)	0.2389 (2)	0.0285 (8)
N7	0.3042 (3)	0.6391 (2)	0.1249 (2)	0.0256 (7)
H7	0.287 (4)	0.7128 (17)	0.117 (2)	0.031*
N13	0.4056 (3)	0.3746 (2)	0.3391 (2)	0.0262 (7)
H13	0.395 (4)	0.333 (3)	0.297 (2)	0.031*
C2	0.3483 (4)	0.6108 (3)	0.2042 (2)	0.0234 (8)
C4	0.4134 (4)	0.6713 (3)	0.3196 (3)	0.0304 (9)
H4	0.4324	0.7296	0.3496	0.037*
C5	0.4204 (4)	0.5693 (3)	0.3616 (3)	0.0266 (9)
H5	0.4425	0.5559	0.4188	0.032*
C6	0.3925 (4)	0.4870 (3)	0.3142 (2)	0.0240 (8)
C8	0.3040 (4)	0.5661 (3)	0.0571 (2)	0.0235 (8)
C9	0.2520 (4)	0.6243 (3)	−0.0223 (2)	0.0241 (8)
C10	0.3278 (5)	0.7128 (4)	−0.0646 (3)	0.0516 (13)
H10A	0.3121	0.7713	−0.0163	0.077*
H10B	0.2935	0.7483	−0.1157	0.077*
H10C	0.4262	0.6754	−0.0887	0.077*
C11	0.0990 (4)	0.6824 (4)	0.0157 (3)	0.0479 (12)
H11A	0.0835	0.7404	0.0642	0.072*
H11B	0.0506	0.6256	0.0424	0.072*
H11C	0.0644	0.7184	−0.0352	0.072*
C12	0.2773 (5)	0.5344 (3)	−0.0978 (3)	0.0490 (12)
H12A	0.2445	0.5706	−0.1493	0.073*
H12B	0.2281	0.4780	−0.0717	0.073*
H12C	0.3757	0.4966	−0.1211	0.073*
C14	0.4569 (4)	0.3226 (3)	0.4087 (2)	0.0249 (8)
C15	0.4773 (4)	0.1939 (3)	0.4109 (3)	0.0348 (10)
C16	0.3527 (12)	0.1542 (14)	0.4115 (16)	0.049 (4)	0.6
H16A	0.3759	0.0709	0.4125	0.074*	0.6
H16B	0.3252	0.1788	0.3554	0.074*	0.6
H16C	0.2769	0.1873	0.4672	0.074*	0.6
C17	0.580 (3)	0.145 (2)	0.3155 (10)	0.051 (4)	0.6
H17A	0.5968	0.0616	0.3125	0.077*	0.6
H17B	0.6658	0.1637	0.3080	0.077*	0.6
H17C	0.5409	0.1770	0.2653	0.077*	0.6
C18	0.5496 (13)	0.1468 (16)	0.4841 (8)	0.055 (4)	0.6
H18A	0.5631	0.0642	0.4858	0.083*	0.6
H18B	0.4934	0.1826	0.5455	0.083*	0.6
H18C	0.6388	0.1632	0.4680	0.083*	0.6
C16B	0.3332 (17)	0.182 (2)	0.425 (2)	0.049 (5)	0.4
H16G	0.3356	0.1015	0.4267	0.074*	0.4
H16H	0.2996	0.2159	0.3728	0.074*	0.4
H16I	0.2719	0.2221	0.4837	0.074*	0.4
C17B	0.596 (4)	0.128 (3)	0.3298 (18)	0.057 (6)	0.4
H17G	0.6042	0.0467	0.3344	0.085*	0.4
H17H	0.6810	0.1432	0.3322	0.085*	0.4
H17I	0.5782	0.1533	0.2706	0.085*	0.4
C18B	0.493 (2)	0.162 (2)	0.5081 (10)	0.057 (5)	0.4
H18G	0.5070	0.0797	0.5141	0.086*	0.4
H18H	0.4102	0.2028	0.5563	0.086*	0.4
H18I	0.5723	0.1829	0.5158	0.086*	0.4
O8A	0.5012 (3)	0.06266 (19)	0.11110 (18)	0.0308 (6)
O14A	−0.1719 (3)	0.2917 (2)	0.2818 (2)	0.0401 (7)
N1A	0.2274 (3)	0.0794 (2)	0.2012 (2)	0.0241 (7)
N3A	0.1930 (3)	−0.0951 (2)	0.1596 (2)	0.0291 (8)
N7A	0.4086 (3)	−0.0859 (2)	0.1563 (2)	0.0278 (7)
H7A	0.424 (4)	−0.1590 (17)	0.163 (3)	0.033*
N13A	0.0596 (3)	0.2457 (2)	0.2438 (2)	0.0278 (7)
H13A	0.134 (3)	0.268 (3)	0.238 (3)	0.033*
C2A	0.2704 (4)	−0.0302 (3)	0.1724 (2)	0.0246 (8)
C4A	0.0594 (4)	−0.0408 (3)	0.1783 (3)	0.0319 (9)
H4A	−0.0004	−0.0836	0.1721	0.038*
C5A	0.0030 (4)	0.0726 (3)	0.2060 (3)	0.0296 (9)
H5A	−0.0920	0.1087	0.2172	0.035*
C6A	0.0941 (4)	0.1311 (3)	0.2166 (2)	0.0258 (9)
C8A	0.5165 (4)	−0.0389 (3)	0.1257 (2)	0.0236 (8)
C9A	0.6589 (4)	−0.1224 (3)	0.1082 (2)	0.0245 (8)
C10A	0.6809 (4)	−0.2132 (3)	0.0330 (3)	0.0382 (10)
H10D	0.7725	−0.2662	0.0219	0.057*
H10E	0.6728	−0.1764	−0.0250	0.057*
H10F	0.6116	−0.2550	0.0541	0.057*
C11A	0.6756 (4)	−0.1802 (3)	0.1980 (3)	0.0378 (10)
H11D	0.7674	−0.2333	0.1852	0.057*
H11E	0.6065	−0.2219	0.2205	0.057*
H11F	0.6638	−0.1223	0.2457	0.057*
C12A	0.7650 (4)	−0.0561 (3)	0.0739 (3)	0.0340 (10)
H12D	0.8572	−0.1083	0.0619	0.051*
H12E	0.7513	0.0024	0.1217	0.051*
H12F	0.7548	−0.0196	0.0162	0.051*
C14A	−0.0697 (4)	0.3197 (3)	0.2778 (2)	0.0283 (9)
C15A	−0.0712 (4)	0.4379 (3)	0.3093 (3)	0.0303 (9)
C16A	0.0042 (5)	0.4278 (4)	0.3835 (3)	0.0526 (13)
H16D	0.0024	0.5039	0.4034	0.079*
H16E	0.0994	0.3825	0.3573	0.079*
H16F	−0.0411	0.3904	0.4375	0.079*
C17A	0.0004 (4)	0.4968 (3)	0.2252 (3)	0.0396 (11)
H17D	−0.0007	0.5725	0.2455	0.059*
H17E	−0.0480	0.5043	0.1776	0.059*
H17F	0.0954	0.4511	0.1987	0.059*
C18A	−0.2197 (4)	0.5074 (3)	0.3492 (3)	0.0453 (11)
H18D	−0.2227	0.5835	0.3699	0.068*
H18E	−0.2655	0.4693	0.4023	0.068*
H18F	−0.2666	0.5141	0.3009	0.068*
O1	0.3274 (3)	0.2837 (2)	0.19608 (18)	0.0267 (6)
H1A	0.367 (4)	0.219 (2)	0.168 (2)	0.040*
H1B	0.341 (4)	0.336 (3)	0.161 (2)	0.040*
C19	0.0268 (6)	0.7745 (4)	0.3857 (4)	0.0705 (16)
H19A	0.0798	0.6973	0.3935	0.106*	0.6
H19B	0.0354	0.7854	0.3193	0.106*	0.6
H19C	−0.0699	0.7851	0.4205	0.106*	0.6
H19D	0.0647	0.6924	0.3894	0.106*	0.4
H19E	0.0794	0.8003	0.3278	0.106*	0.4
H19F	−0.0692	0.7906	0.3865	0.106*	0.4
C20	0.0808 (9)	0.8604 (8)	0.4226 (8)	0.062 (3)	0.6
H20A	0.1341	0.8212	0.4644	0.074*	0.6
H20B	0.1455	0.8850	0.3690	0.074*	0.6
C20B	0.0356 (16)	0.8381 (9)	0.4706 (8)	0.057 (4)	0.4
H20C	−0.0158	0.8098	0.5287	0.068*	0.4
H20D	0.1327	0.8194	0.4701	0.068*	0.4
C21	−0.0176 (6)	0.9607 (4)	0.4725 (4)	0.0702 (16)
H21A	−0.0932	0.9351	0.5157	0.084*	0.6
H21B	−0.0562	1.0066	0.4261	0.084*	0.6
H21C	−0.1187	0.9775	0.4932	0.084*	0.4
H21D	0.0081	0.9829	0.4069	0.084*	0.4

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O8	0.0437 (18)	0.0156 (13)	0.0338 (15)	−0.0028 (12)	−0.0177 (13)	0.0011 (11)
O14	0.0485 (19)	0.0318 (15)	0.0313 (15)	−0.0069 (13)	−0.0216 (14)	−0.0006 (12)
N1	0.0280 (19)	0.0180 (15)	0.0295 (17)	−0.0078 (13)	−0.0159 (14)	0.0030 (13)
N3	0.034 (2)	0.0175 (16)	0.0382 (19)	−0.0080 (14)	−0.0167 (16)	0.0020 (14)
N7	0.032 (2)	0.0144 (15)	0.0355 (18)	−0.0059 (14)	−0.0184 (15)	0.0034 (14)
N13	0.039 (2)	0.0172 (16)	0.0276 (17)	−0.0072 (14)	−0.0189 (15)	0.0037 (13)
C2	0.027 (2)	0.0165 (18)	0.030 (2)	−0.0055 (16)	−0.0129 (17)	0.0023 (15)
C4	0.031 (2)	0.023 (2)	0.040 (2)	−0.0082 (17)	−0.0135 (19)	−0.0071 (17)
C5	0.029 (2)	0.025 (2)	0.030 (2)	−0.0089 (17)	−0.0129 (18)	0.0015 (16)
C6	0.023 (2)	0.0225 (19)	0.026 (2)	−0.0062 (16)	−0.0078 (17)	0.0005 (16)
C8	0.019 (2)	0.023 (2)	0.027 (2)	−0.0051 (16)	−0.0056 (16)	0.0030 (16)
C9	0.026 (2)	0.0224 (18)	0.0233 (19)	−0.0047 (16)	−0.0092 (16)	0.0057 (15)
C10	0.068 (3)	0.045 (3)	0.053 (3)	−0.028 (2)	−0.026 (3)	0.023 (2)
C11	0.034 (3)	0.061 (3)	0.042 (3)	0.004 (2)	−0.016 (2)	0.010 (2)
C12	0.068 (3)	0.036 (2)	0.039 (2)	0.004 (2)	−0.027 (2)	−0.002 (2)
C14	0.021 (2)	0.0254 (19)	0.026 (2)	−0.0057 (16)	−0.0052 (17)	0.0038 (16)
C15	0.046 (3)	0.025 (2)	0.046 (2)	−0.0164 (18)	−0.027 (2)	0.0111 (18)
C16	0.047 (6)	0.034 (8)	0.084 (8)	−0.021 (5)	−0.036 (6)	0.010 (6)
C17	0.055 (7)	0.016 (6)	0.081 (7)	0.006 (4)	−0.033 (5)	0.000 (5)
C18	0.069 (8)	0.041 (7)	0.082 (7)	−0.025 (7)	−0.056 (6)	0.032 (6)
C16B	0.056 (8)	0.026 (9)	0.063 (9)	−0.024 (7)	−0.003 (7)	0.017 (7)
C17B	0.050 (10)	0.031 (11)	0.088 (11)	−0.007 (8)	−0.020 (10)	0.002 (9)
C18B	0.087 (13)	0.044 (8)	0.058 (8)	−0.015 (11)	−0.052 (8)	0.020 (7)
O8A	0.0267 (16)	0.0167 (13)	0.0484 (16)	−0.0057 (11)	−0.0105 (13)	0.0062 (11)
O14A	0.0256 (17)	0.0328 (16)	0.061 (2)	−0.0081 (13)	−0.0100 (14)	−0.0021 (13)
N1A	0.0225 (19)	0.0166 (15)	0.0345 (17)	−0.0053 (13)	−0.0103 (14)	0.0016 (13)
N3A	0.030 (2)	0.0208 (16)	0.0425 (19)	−0.0107 (15)	−0.0159 (16)	0.0030 (14)
N7A	0.0260 (19)	0.0146 (15)	0.047 (2)	−0.0060 (14)	−0.0175 (16)	0.0045 (14)
N13A	0.023 (2)	0.0195 (16)	0.0410 (19)	−0.0089 (14)	−0.0061 (16)	−0.0016 (14)
C2A	0.026 (2)	0.0202 (19)	0.030 (2)	−0.0070 (17)	−0.0110 (17)	0.0066 (16)
C4A	0.031 (3)	0.026 (2)	0.047 (2)	−0.0133 (18)	−0.019 (2)	0.0019 (18)
C5A	0.022 (2)	0.025 (2)	0.043 (2)	−0.0055 (17)	−0.0113 (18)	−0.0041 (17)
C6A	0.026 (2)	0.0202 (19)	0.031 (2)	−0.0051 (17)	−0.0103 (17)	0.0018 (16)
C8A	0.026 (2)	0.0194 (19)	0.0271 (19)	−0.0041 (16)	−0.0131 (17)	0.0006 (15)
C9A	0.024 (2)	0.0181 (18)	0.033 (2)	−0.0031 (15)	−0.0123 (17)	0.0007 (15)
C10A	0.039 (3)	0.025 (2)	0.049 (3)	0.0015 (18)	−0.019 (2)	−0.0084 (18)
C11A	0.038 (3)	0.033 (2)	0.043 (2)	−0.0048 (19)	−0.018 (2)	0.0049 (19)
C12A	0.024 (2)	0.033 (2)	0.043 (2)	−0.0019 (18)	−0.0111 (19)	−0.0002 (18)
C14A	0.025 (2)	0.029 (2)	0.027 (2)	−0.0035 (18)	−0.0050 (17)	0.0010 (16)
C15A	0.028 (2)	0.029 (2)	0.033 (2)	−0.0038 (17)	−0.0112 (18)	−0.0036 (17)
C16A	0.068 (4)	0.043 (3)	0.051 (3)	−0.007 (2)	−0.030 (3)	−0.008 (2)
C17A	0.039 (3)	0.024 (2)	0.052 (3)	−0.0083 (19)	−0.008 (2)	−0.0008 (19)
C18A	0.036 (3)	0.034 (2)	0.053 (3)	−0.003 (2)	0.002 (2)	−0.013 (2)
O1	0.0328 (17)	0.0163 (13)	0.0333 (15)	−0.0067 (12)	−0.0131 (13)	0.0009 (11)
C19	0.073 (4)	0.056 (3)	0.070 (4)	−0.025 (3)	0.005 (3)	−0.013 (3)
C20	0.038 (6)	0.059 (6)	0.075 (7)	−0.017 (5)	0.007 (5)	−0.020 (6)
C20B	0.049 (10)	0.041 (7)	0.062 (9)	−0.014 (6)	0.010 (7)	0.008 (7)
C21	0.075 (4)	0.059 (3)	0.077 (4)	−0.021 (3)	−0.019 (3)	−0.007 (3)

Geometric parameters (Å, º) top

O8—C8	1.221 (4)	N3A—C4A	1.340 (5)
O14—C14	1.216 (4)	N7A—C8A	1.373 (5)
N1—C2	1.321 (4)	N7A—C2A	1.390 (5)
N1—C6	1.343 (4)	N7A—H7A	0.871 (18)
N3—C2	1.343 (4)	N13A—C14A	1.381 (5)
N3—C4	1.347 (5)	N13A—C6A	1.391 (4)
N7—C8	1.375 (4)	N13A—H13A	0.886 (18)
N7—C2	1.398 (5)	C4A—C5A	1.375 (5)
N7—H7	0.881 (18)	C4A—H4A	0.9500
N13—C14	1.372 (5)	C5A—C6A	1.394 (5)
N13—C6	1.392 (4)	C5A—H5A	0.9500
N13—H13	0.870 (18)	C8A—C9A	1.529 (5)
C4—C5	1.370 (5)	C9A—C12A	1.523 (5)
C4—H4	0.9500	C9A—C10A	1.530 (5)
C5—C6	1.391 (5)	C9A—C11A	1.531 (5)
C5—H5	0.9500	C10A—H10D	0.9800
C8—C9	1.528 (5)	C10A—H10E	0.9800
C9—C12	1.517 (5)	C10A—H10F	0.9800
C9—C11	1.524 (5)	C11A—H11D	0.9800
C9—C10	1.532 (5)	C11A—H11E	0.9800
C10—H10A	0.9800	C11A—H11F	0.9800
C10—H10B	0.9800	C12A—H12D	0.9800
C10—H10C	0.9800	C12A—H12E	0.9800
C11—H11A	0.9800	C12A—H12F	0.9800
C11—H11B	0.9800	C14A—C15A	1.529 (5)
C11—H11C	0.9800	C15A—C18A	1.522 (5)
C12—H12A	0.9800	C15A—C16A	1.531 (5)
C12—H12B	0.9800	C15A—C17A	1.537 (5)
C12—H12C	0.9800	C16A—H16D	0.9800
C14—C15	1.529 (5)	C16A—H16E	0.9800
C15—C16	1.524 (10)	C16A—H16F	0.9800
C15—C17B	1.525 (13)	C17A—H17D	0.9800
C15—C18	1.526 (10)	C17A—H17E	0.9800
C15—C16B	1.527 (13)	C17A—H17F	0.9800
C15—C18B	1.539 (12)	C18A—H18D	0.9800
C15—C17	1.543 (10)	C18A—H18E	0.9800
C16—H16A	0.9800	C18A—H18F	0.9800
C16—H16B	0.9800	O1—H1A	0.841 (19)
C16—H16C	0.9800	O1—H1B	0.828 (18)
C17—H17A	0.9800	C19—C20	1.512 (9)
C17—H17B	0.9800	C19—C20B	1.550 (12)
C17—H17C	0.9800	C19—H19A	0.9800
C18—H18A	0.9800	C19—H19B	0.9800
C18—H18B	0.9800	C19—H19C	0.9800
C18—H18C	0.9800	C19—H19D	0.9800
C16B—H16G	0.9800	C19—H19E	0.9800
C16B—H16H	0.9800	C19—H19F	0.9800
C16B—H16I	0.9800	C20—C21	1.435 (9)
C17B—H17G	0.9800	C20—H20A	0.9900
C17B—H17H	0.9800	C20—H20B	0.9900
C17B—H17I	0.9800	C20B—C21	1.447 (11)
C18B—H18G	0.9800	C20B—H20C	0.9900
C18B—H18H	0.9800	C20B—H20D	0.9900
C18B—H18I	0.9800	C21—C21ⁱ	1.473 (10)
O8A—C8A	1.227 (4)	C21—H21A	0.9900
O14A—C14A	1.208 (4)	C21—H21B	0.9900
N1A—C2A	1.334 (4)	C21—H21C	0.9900
N1A—C6A	1.336 (5)	C21—H21D	0.9900
N3A—C2A	1.339 (4)

C2—N1—C6	116.2 (3)	C6A—N13A—H13A	111 (3)
C2—N3—C4	113.6 (3)	N1A—C2A—N3A	126.7 (3)
C8—N7—C2	127.7 (3)	N1A—C2A—N7A	117.9 (3)
C8—N7—H7	120 (2)	N3A—C2A—N7A	115.3 (3)
C2—N7—H7	112 (2)	N3A—C4A—C5A	124.4 (3)
C14—N13—C6	127.1 (3)	N3A—C4A—H4A	117.8
C14—N13—H13	120 (2)	C5A—C4A—H4A	117.8
C6—N13—H13	112 (2)	C4A—C5A—C6A	115.8 (4)
N1—C2—N3	127.5 (3)	C4A—C5A—H5A	122.1
N1—C2—N7	118.9 (3)	C6A—C5A—H5A	122.1
N3—C2—N7	113.7 (3)	N1A—C6A—N13A	112.8 (3)
N3—C4—C5	125.0 (3)	N1A—C6A—C5A	121.7 (3)
N3—C4—H4	117.5	N13A—C6A—C5A	125.5 (3)
C5—C4—H4	117.5	O8A—C8A—N7A	122.8 (3)
C4—C5—C6	114.9 (3)	O8A—C8A—C9A	121.7 (3)
C4—C5—H5	122.5	N7A—C8A—C9A	115.4 (3)
C6—C5—H5	122.5	C12A—C9A—C8A	108.2 (3)
N1—C6—C5	122.4 (3)	C12A—C9A—C10A	109.1 (3)
N1—C6—N13	112.6 (3)	C8A—C9A—C10A	109.9 (3)
C5—C6—N13	124.9 (3)	C12A—C9A—C11A	109.5 (3)
O8—C8—N7	123.0 (3)	C8A—C9A—C11A	110.8 (3)
O8—C8—C9	122.1 (3)	C10A—C9A—C11A	109.4 (3)
N7—C8—C9	114.9 (3)	C9A—C10A—H10D	109.5
C12—C9—C11	110.0 (3)	C9A—C10A—H10E	109.5
C12—C9—C8	108.6 (3)	H10D—C10A—H10E	109.5
C11—C9—C8	108.9 (3)	C9A—C10A—H10F	109.5
C12—C9—C10	108.8 (3)	H10D—C10A—H10F	109.5
C11—C9—C10	109.6 (3)	H10E—C10A—H10F	109.5
C8—C9—C10	110.9 (3)	C9A—C11A—H11D	109.5
C9—C10—H10A	109.5	C9A—C11A—H11E	109.5
C9—C10—H10B	109.5	H11D—C11A—H11E	109.5
H10A—C10—H10B	109.5	C9A—C11A—H11F	109.5
C9—C10—H10C	109.5	H11D—C11A—H11F	109.5
H10A—C10—H10C	109.5	H11E—C11A—H11F	109.5
H10B—C10—H10C	109.5	C9A—C12A—H12D	109.5
C9—C11—H11A	109.5	C9A—C12A—H12E	109.5
C9—C11—H11B	109.5	H12D—C12A—H12E	109.5
H11A—C11—H11B	109.5	C9A—C12A—H12F	109.5
C9—C11—H11C	109.5	H12D—C12A—H12F	109.5
H11A—C11—H11C	109.5	H12E—C12A—H12F	109.5
H11B—C11—H11C	109.5	O14A—C14A—N13A	121.9 (3)
C9—C12—H12A	109.5	O14A—C14A—C15A	123.7 (3)
C9—C12—H12B	109.5	N13A—C14A—C15A	114.4 (3)
H12A—C12—H12B	109.5	C18A—C15A—C14A	108.4 (3)
C9—C12—H12C	109.5	C18A—C15A—C16A	110.2 (3)
H12A—C12—H12C	109.5	C14A—C15A—C16A	110.1 (3)
H12B—C12—H12C	109.5	C18A—C15A—C17A	109.6 (3)
O14—C14—N13	122.6 (3)	C14A—C15A—C17A	109.6 (3)
O14—C14—C15	122.2 (3)	C16A—C15A—C17A	109.0 (4)
N13—C14—C15	115.2 (3)	C15A—C16A—H16D	109.5
C16—C15—C18	117.0 (11)	C15A—C16A—H16E	109.5
C17B—C15—C16B	120 (2)	H16D—C16A—H16E	109.5
C16—C15—C14	115.5 (7)	C15A—C16A—H16F	109.5
C17B—C15—C14	112.8 (18)	H16D—C16A—H16F	109.5
C18—C15—C14	109.1 (8)	H16E—C16A—H16F	109.5
C16B—C15—C14	103.2 (10)	C15A—C17A—H17D	109.5
C17B—C15—C18B	114.3 (16)	C15A—C17A—H17E	109.5
C16B—C15—C18B	99.5 (15)	H17D—C17A—H17E	109.5
C14—C15—C18B	105.2 (12)	C15A—C17A—H17F	109.5
C16—C15—C17	102.4 (16)	H17D—C17A—H17F	109.5
C18—C15—C17	106.1 (11)	H17E—C17A—H17F	109.5
C14—C15—C17	105.5 (11)	C15A—C18A—H18D	109.5
C15—C16—H16A	109.5	C15A—C18A—H18E	109.5
C15—C16—H16B	109.5	H18D—C18A—H18E	109.5
H16A—C16—H16B	109.5	C15A—C18A—H18F	109.5
C15—C16—H16C	109.5	H18D—C18A—H18F	109.5
H16A—C16—H16C	109.5	H18E—C18A—H18F	109.5
H16B—C16—H16C	109.5	H1A—O1—H1B	111 (4)
C15—C17—H17A	109.5	C20—C19—H19A	109.5
C15—C17—H17B	109.5	C20—C19—H19B	109.5
H17A—C17—H17B	109.5	H19A—C19—H19B	109.5
C15—C17—H17C	109.5	C20—C19—H19C	109.5
H17A—C17—H17C	109.5	H19A—C19—H19C	109.5
H17B—C17—H17C	109.5	H19B—C19—H19C	109.5
C15—C18—H18A	109.5	C20B—C19—H19D	109.5
C15—C18—H18B	109.5	C20B—C19—H19E	109.5
H18A—C18—H18B	109.5	H19D—C19—H19E	109.5
C15—C18—H18C	109.5	C20B—C19—H19F	109.5
H18A—C18—H18C	109.5	H19D—C19—H19F	109.5
H18B—C18—H18C	109.5	H19E—C19—H19F	109.5
C15—C16B—H16G	109.5	C21—C20—C19	117.4 (7)
C15—C16B—H16H	109.5	C21—C20—H20A	107.9
H16G—C16B—H16H	109.5	C19—C20—H20A	107.9
C15—C16B—H16I	109.5	C21—C20—H20B	107.9
H16G—C16B—H16I	109.5	C19—C20—H20B	107.9
H16H—C16B—H16I	109.5	H20A—C20—H20B	107.2
C15—C17B—H17G	109.5	C21—C20B—C19	114.3 (9)
C15—C17B—H17H	109.5	C21—C20B—H20C	108.7
H17G—C17B—H17H	109.5	C19—C20B—H20C	108.7
C15—C17B—H17I	109.5	C21—C20B—H20D	108.7
H17G—C17B—H17I	109.5	C19—C20B—H20D	108.7
H17H—C17B—H17I	109.5	H20C—C20B—H20D	107.6
C15—C18B—H18G	109.5	C20—C21—C21ⁱ	122.8 (7)
C15—C18B—H18H	109.5	C20B—C21—C21ⁱ	123.2 (8)
H18G—C18B—H18H	109.5	C20—C21—H21A	106.6
C15—C18B—H18I	109.5	C21ⁱ—C21—H21A	106.6
H18G—C18B—H18I	109.5	C20—C21—H21B	106.6
H18H—C18B—H18I	109.5	C21ⁱ—C21—H21B	106.6
C2A—N1A—C6A	116.9 (3)	H21A—C21—H21B	106.6
C2A—N3A—C4A	114.4 (3)	C20B—C21—H21C	106.5
C8A—N7A—C2A	126.9 (3)	C21ⁱ—C21—H21C	106.5
C8A—N7A—H7A	120 (3)	C20B—C21—H21D	106.5
C2A—N7A—H7A	113 (3)	C21ⁱ—C21—H21D	106.5
C14A—N13A—C6A	127.9 (3)	H21C—C21—H21D	106.5
C14A—N13A—H13A	121 (2)

C6—N1—C2—N3	−0.1 (6)	C6A—N1A—C2A—N3A	−1.8 (5)
C6—N1—C2—N7	−179.1 (3)	C6A—N1A—C2A—N7A	−179.7 (3)
C4—N3—C2—N1	−4.2 (5)	C4A—N3A—C2A—N1A	0.0 (5)
C4—N3—C2—N7	174.9 (3)	C4A—N3A—C2A—N7A	177.9 (3)
C8—N7—C2—N1	−23.1 (6)	C8A—N7A—C2A—N1A	−31.5 (5)
C8—N7—C2—N3	157.8 (3)	C8A—N7A—C2A—N3A	150.3 (3)
C2—N3—C4—C5	3.9 (6)	C2A—N3A—C4A—C5A	1.8 (5)
N3—C4—C5—C6	0.4 (6)	N3A—C4A—C5A—C6A	−1.7 (6)
C2—N1—C6—C5	5.0 (5)	C2A—N1A—C6A—N13A	−178.2 (3)
C2—N1—C6—N13	−174.1 (3)	C2A—N1A—C6A—C5A	1.9 (5)
C4—C5—C6—N1	−5.1 (5)	C14A—N13A—C6A—N1A	−169.9 (3)
C4—C5—C6—N13	173.9 (4)	C14A—N13A—C6A—C5A	10.0 (6)
C14—N13—C6—N1	173.8 (3)	C4A—C5A—C6A—N1A	−0.3 (5)
C14—N13—C6—C5	−5.3 (6)	C4A—C5A—C6A—N13A	179.9 (3)
C2—N7—C8—O8	1.9 (6)	C2A—N7A—C8A—O8A	2.1 (6)
C2—N7—C8—C9	−178.6 (3)	C2A—N7A—C8A—C9A	−176.3 (3)
O8—C8—C9—C12	−8.7 (5)	O8A—C8A—C9A—C12A	1.1 (5)
N7—C8—C9—C12	171.8 (3)	N7A—C8A—C9A—C12A	179.4 (3)
O8—C8—C9—C11	111.1 (4)	O8A—C8A—C9A—C10A	−117.9 (4)
N7—C8—C9—C11	−68.4 (4)	N7A—C8A—C9A—C10A	60.4 (4)
O8—C8—C9—C10	−128.2 (4)	O8A—C8A—C9A—C11A	121.0 (4)
N7—C8—C9—C10	52.3 (4)	N7A—C8A—C9A—C11A	−60.6 (4)
C6—N13—C14—O14	8.2 (6)	C6A—N13A—C14A—O14A	−5.3 (6)
C6—N13—C14—C15	−171.8 (3)	C6A—N13A—C14A—C15A	174.7 (3)
O14—C14—C15—C16	127.7 (10)	O14A—C14A—C15A—C18A	2.7 (5)
N13—C14—C15—C16	−52.3 (10)	N13A—C14A—C15A—C18A	−177.3 (3)
O14—C14—C15—C17B	−109 (2)	O14A—C14A—C15A—C16A	123.3 (4)
N13—C14—C15—C17B	71 (2)	N13A—C14A—C15A—C16A	−56.7 (4)
O14—C14—C15—C18	−6.4 (7)	O14A—C14A—C15A—C17A	−116.8 (4)
N13—C14—C15—C18	173.6 (6)	N13A—C14A—C15A—C17A	63.2 (4)
O14—C14—C15—C16B	120.1 (13)	C20B—C19—C20—C21	−64.2 (11)
N13—C14—C15—C16B	−59.9 (13)	C20—C19—C20B—C21	60.4 (10)
O14—C14—C15—C18B	16.2 (10)	C19—C20—C21—C20B	65.7 (12)
N13—C14—C15—C18B	−163.8 (9)	C19—C20—C21—C21ⁱ	167.6 (7)
O14—C14—C15—C17	−120.0 (13)	C19—C20B—C21—C20	−60.0 (10)
N13—C14—C15—C17	60.0 (13)	C19—C20B—C21—C21ⁱ	−160.5 (8)

Symmetry code: (i) −x, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O8A	0.84 (2)	2.08 (2)	2.910 (3)	167 (4)
O1—H1A···N1A	0.84 (2)	2.51 (4)	2.958 (4)	115 (3)
O1—H1B···O8	0.83 (2)	2.13 (2)	2.943 (3)	168 (4)
O1—H1B···N1	0.83 (2)	2.48 (4)	2.931 (4)	115 (3)
N7—H7···N3Aⁱⁱ	0.88 (2)	2.32 (2)	3.144 (4)	156 (3)
N13—H13···O1	0.87 (2)	2.02 (2)	2.864 (4)	162 (4)
N7A—H7A···N3ⁱⁱⁱ	0.87 (2)	2.16 (2)	2.958 (4)	152 (3)
N13A—H13A···O1	0.89 (2)	2.02 (2)	2.882 (4)	164 (4)
C5—H5···O14^iv	0.95	2.37	3.205 (5)	147

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O8A	0.841 (19)	2.08 (2)	2.910 (3)	167 (4)
O1—H1A···N1A	0.841 (19)	2.51 (4)	2.958 (4)	115 (3)
O1—H1B···O8	0.828 (18)	2.13 (2)	2.943 (3)	168 (4)
O1—H1B···N1	0.828 (18)	2.48 (4)	2.931 (4)	115 (3)
N7—H7···N3Aⁱ	0.881 (18)	2.32 (2)	3.144 (4)	156 (3)
N13—H13···O1	0.870 (18)	2.02 (2)	2.864 (4)	162 (4)
N7A—H7A···N3ⁱⁱ	0.871 (18)	2.16 (2)	2.958 (4)	152 (3)
N13A—H13A···O1	0.886 (18)	2.02 (2)	2.882 (4)	164 (4)
C5—H5···O14ⁱⁱⁱ	0.95	2.37	3.205 (5)	147

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

Acknowledgements

The financial support from the National Science Centre in Kraków (grant No. NCN204 356840) is gratefully acknowledged. Academy Professor Kari Rissanen is also gratefully acknowledged for financial support (Academy of Finland grant Nos. 122350, 140718, 265328 and 263256).

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Volume 69| Part 11| November 2013| Pages o1617-o1618

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N-[2-(2,2-Di­methyl­propanamido)­pyrimidin-4-yl]-2,2-di­methyl­propanamide n-hexane 0.25-solvate hemihydrate

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Experimental

Crystal data

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Refinement

Supporting information

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organic compounds

N-[2-(2,2-Dimethylpropanamido)pyrimidin-4-yl]-2,2-dimethylpropanamide n-hexane 0.25-solvate hemihydrate