Hydro­gen bonding in 2-amino-4-methoxy-6-methyl­pyrimidine, 2-benzyl­amino-4-benzyl­oxy-6-methyl­pyrimidine and 4-benzyl­amino-2,6-bis­(benzyl­oxy)­pyrimidine: π-stacked chains of fused R₂²(8) rings, and centrosymmetric R₂²(8) dimers

Molecules of 2-amino-4-methoxy-6-methyl­pyrimidine, C₆H₉N₃O, (I), lie on mirror planes in space group Pnma and are linked by two N—H...N hydrogen bonds [H...N = 2.26 and 2.34 Å, N...N = 3.136 (2) and 3.212 (2) Å, and N—H...N = 175 and 172°] into chains of edge-fused R(8) rings, which themselves are linked into sheets by aromatic π–π-stacking interactions. In 2-benzyl­amino-4-benzyl­oxy-6-methyl­pyri­mi­dine, C₁₉H₁₉N₃O, (II), and 4-benzyl­amino-2,6-bis­(benzyl­oxy)­pyrimidine, C₂₅H₂₃N₃O₂, (III), the mol­ecules are linked by paired N—H...N hydrogen bonds [H...N = 2.16 Å, N...N = 3.039 (2) Å and N—H...N = 165° in (II); H...N = 2.15 Å, N...N = 2.980 (2) Å and N—H...N = 176° in (III)] into centrosymmetric R(8) dimers, with no direction-specific interactions between these dimeric units.

S1. Comment

Alkoxypyrimidines are key intermediates for the synthesis of a wide range of alkoxy- and amino-substituted O⁶-benzyloxy-5-nitrosopyrimidines (Marchal et al., 1998, 2000; Quesada et al., 2000), important as potential, or proven, in vitro inhibitors of the human DNA-repair protein O⁶-alkylguanine-DNA-transferase (Chae et al., 1995; Quesada et al., 2002). We report here the molecular and supramolecular structures of three examples of this class, namely 2-amino-4-methoxy-6-methylpyrimidine, (I), 2-benzylamino-4-benzyloxy-6-methylpyrimidine, (II), and 4-benzylamino-2,6-bis(benzyloxy)pyrimidine, (III).

Compound (I) (Fig. 1) crystallizes in space group Pnma with all non-H atoms lying on mirror planes, with the plane for the reference molecule selected as that at y = 0.25. The molecules are linked by two N—H···N hydrogen bonds (Table 2) into chains of edge-fused rings, which themselves are linked into sheets by π–π-stacking interactions. The amino atom N2 in the reference molecule at (x, 1/4, z) acts as hydrogen-bond donor, via H1 and H2, respectively, to atom N1 in the molecule at (−0.5 + x, 1/4, 0.5 − z) and to atom N3 in that at (0.5 + x, 1/4, 0.5 − z), and propagation of these two hydrogen bonds generates a chain of edge-fused R²₂(8) rings running parallel to the [100] direction and generated by the a-glide plane at z = 0.25 (Fig. 2). This hydrogen-bonded substructure may alternatively be regarded as a molecular ladder, in which two C²₂(6) chains, related by the glide plane at z = 1/4, act as the uprights and the C2—N2 bonds act as the rungs.

The π–π-stacking interactions (Fig. 3) link the reference molecule at (x, 1/4, z), which forms part of the hydrogen-bonded chain along (x, 1/4, 1/4), with the two molecules at (1 − x, 3/4, 1 − z) and (1 − x, −0.25, 1 − z), which lie, respectively, in the hydrogen-bonded chains along (-x, 3/4, 3/4) and (-x, −0.25, 3/4). The interplanar spacing is 3.273 (2) Å, the centroid separation is 3.588 (2) Å and the centroid offset is 1.470 (2) Å. By this means, a (001) sheet is formed, centred at z = 0.5 and lying in the domain 0.22 < z < 0.78; a similar sheet, centred at z = 0, lies in the domain −0.28 < z < 0.28, but there are no direction-specific interactions between adjacent sheets.

In both (II) (Fig. 4) and (III) (Fig. 5), there is just a single N—H bond, and a single N—H···N hydrogen bond (Tables 4 and 6) leads to the formation of centrosymmetric R²₂(8) dimers, centred at (1/2, 1/2, 1/2) (Figs. 6 and 7). In neither of (II) and (III) are there any other hydrogen bonds or any π–π-stacking interactions.

The gross supramolecular structure of (I) resembles that of the 4,6-dimethoxy analogue, (IV) (Low et al., 2002), while differing from it in detail. The chains of edge-fused rings in (IV) contain two different types of R²₂(8) ring, both centrosymmetric, incorporating only atoms N1 and N2 in one type of ring and only N2 and N3 in the other; by contrast, the chain in (I) contains only one type of ring, and this includes all three N atoms. Moreover, whereas in (I), the chain is generated by a glide plane, in (IV) it is generated by a combination of inversions and twofold rotations. The supramolecular structures of (I) and (IV) also differsin the effects of the π–π stacking, which gives a two-dimensional array in (I), but a three-dimensional structure in (IV). On the other hand, the centrosymmetric dimer structures found for (II) and (III) exactly mimic that observed in (V) (Low et al., 2002), which is a positional isomer of (III).

In each of (I)–(III), the intramolecular distances show no evidence for significant bond fixation involving the pyrimidine rings (Tables 1, 3 and 5); in this respect, the molecular–electronic structure of (I) is markedly different from those in a large number of analogous pyrimidines carrying a 5-nitroso substituent, where highly polarized structures are the norm (Low et al., 2000; Low, Cannon et al., 2001; Low, Moreno et al., 2001; Quesada et al., 2002).

The non-H atoms in (I) are strictly coplanar, and the methoxy-group conformation is such that the methyl C atom is directed away from the amino group [cf. compound (IV) (Low et al., 2002), see Scheme]. In both (II) and (III), the methylene C atoms of the benzyl substituents are all close to the planes of the adjacent pyrimidine rings, but the phenyl groups are twisted well out of these planes (Tables 3 and 5). We note the general similarity between the conformations of (II) and (III), and the fact that the overall conformations of the isomeric compounds (III) and (V) are unchanged by the positional exchange of benzylamino and benzyloxy substituents. The subtle factors underpinning the preferred conformations is systems such as (I)–(V) await investigation.

S2. Experimental

A sample of compound (I) was purchased from Aldrich and converted to (II) (m. p. 475 K) using the transalkoxylation and N-benzylation methodology previously described by Low et al. (2002). Compound (III) (m. p. 408 K) was likewise prepared from 4-amino-2-methylthio-6-methoxypyrimidine (Pfleiderer & Liedek, 1958). ¹H NMR (DMSO-d₆, p.p.m), for (II): δ 2.15 (s, 3H, CH₃), 4.47 (d, 2H, N–CH₂, J = 6.31 Hz), 5.28 (s, 2H, O—CH₂), 5.93 (s, 1H, C5—H), 7.26 (m, 10H, 2 × Ph), 7.55 (br s, 1H, NH, exchanges with D₂O); for (III): δ 4.42 (d, 2H, NH–CH₂, J = 5.28 Hz), 5.32 (s, 2H, O—CH₂), 5.33 (s, 2H, O–CH₂), 5.41 (s, 1H, C5–H), 5.43 (br s, 1H, NH exchanges with D₂O), 7.29 (m, 15H, 3 × Ph). Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of solutions in ethyl acetate [for (I)], ethanol [for (II)] and n-butanol [for (III)].

S3. Refinement

For compound (I), the systematic absences permitted Pnma (= Pnam) and Pna2₁ as possible space groups; Pnma was selected and confirmed by the analysis. For both (II) and (III), space group P2₁/c was uniquely assigned from the systematic absences. All H atoms were treated as riding, with C—H distances of C—H = 0.95 (aromatic), 0.98 (CH₃) or 0.99 Å (CH₂), and N—H distances of 0.88 Å. The methyl groups in (I) were both modelled using six half-occupancy H-atom sites offset from one another by 60°.

Computing details

For all compounds, data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2002); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures

	Fig. 1. The molecule of compound (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. All the non-H atoms lie on a mirror plane. For the sake of clarity, only one set of half-occupancy H-atom sites is shown for each of the methyl groups.
	Fig. 2. Part of the crystal structure of (I), showing the formation of a chain of edge-fused rings along [100]. For the sake of clarity, H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk (*) or hash (#) are at the symmetry positions (0.5 + x, 1/4, 0.5 − z) and (−0.5 + x, 1/4, 0.5 − z), respectively.
	Fig. 3. Part of the crystal structure of (I), showing the π–π-stacking interactions. For the sake of clarity, H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk (*) or hash (#) are at the symmetry positions (1 − x, 3/4, 1 − z) and (1 − x, −0.25, 1 − z), respectively.
	Fig. 4. The molecule of compound (II), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 5. The molecule of compound (III), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 6. Part of the crystal structure of (II), showing the formation of a centrosymmetric R^22(8) dimer. For the sake of clarity, H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk are at the symmetry position (1 − x, 1 − y, 1 − z).
	Fig. 7. Part of the crystal structure of (III), showing the formation of a centrosymmetric R^22(8) dimer. For the sake of clarity, H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk are at the symmetry position (1 − x, 1 − y, 1 − z).

(I) 2-Amino-4-methoxy-6-methylpyrimidine

Crystal data

C6H9N3O	F(000) = 296
Mr = 139.16	Dx = 1.411 Mg m^−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 797 reflections
a = 8.1442 (17) Å	θ = 3.0–27.4°
b = 6.5456 (11) Å	µ = 0.10 mm^−1
c = 12.285 (2) Å	T = 120 K
V = 654.9 (2) Å^3	Plate, colourless
Z = 4	0.25 × 0.20 × 0.02 mm

Data collection

Nonius KappaCCD diffractometer	468 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tube	Rint = 0.099
Graphite monochromator	θmax = 27.4°, θmin = 3.0°
ϕ scans and ω scans with κ offsets	h = −10→10
7372 measured reflections	k = −8→8
797 independent reflections	l = −10→15

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.136	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.0795P)^2] where P = (Fo^2 + 2Fc^2)/3
797 reflections	(Δ/σ)max < 0.001
61 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.6539 (2)	0.2500	0.38300 (14)	0.0247 (5)
N2	0.50228 (17)	0.2500	0.22581 (14)	0.0303 (6)
C2	0.5046 (2)	0.2500	0.33456 (18)	0.0234 (5)
N3	0.3588 (2)	0.2500	0.38607 (13)	0.0246 (5)
C4	0.3649 (2)	0.2500	0.49404 (18)	0.0234 (6)
O4	0.21476 (15)	0.2500	0.54049 (11)	0.0277 (5)
C41	0.2082 (2)	0.2500	0.65685 (16)	0.0301 (6)
C5	0.5107 (2)	0.2500	0.55251 (18)	0.0245 (6)
C6	0.6537 (3)	0.2500	0.49193 (18)	0.0248 (6)
C61	0.8176 (2)	0.2500	0.54723 (17)	0.0300 (6)
H1	0.4080	0.2500	0.1909	0.036*
H2	0.5951	0.2500	0.1891	0.036*
H41A	0.0936	0.2399	0.6806	0.045*	0.50
H41B	0.2562	0.3770	0.6846	0.045*	0.50
H41C	0.2703	0.1331	0.6850	0.045*	0.50
H5	0.5122	0.2500	0.6298	0.029*
H61A	0.8982	0.3195	0.5009	0.045*	0.50
H61B	0.8529	0.1088	0.5599	0.045*	0.50
H61C	0.8090	0.3217	0.6170	0.045*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0185 (10)	0.0332 (11)	0.0223 (12)	0.000	−0.0014 (7)	0.000
N2	0.0215 (11)	0.0485 (13)	0.0209 (13)	0.000	0.0003 (7)	0.000
C2	0.0202 (12)	0.0267 (13)	0.0234 (14)	0.000	−0.0007 (8)	0.000
N3	0.0212 (10)	0.0323 (11)	0.0204 (13)	0.000	0.0006 (7)	0.000
C4	0.0163 (12)	0.0283 (13)	0.0257 (14)	0.000	0.0015 (8)	0.000
O4	0.0186 (8)	0.0438 (10)	0.0206 (9)	0.000	0.0025 (6)	0.000
C41	0.0239 (12)	0.0445 (15)	0.0218 (14)	0.000	0.0044 (9)	0.000
C5	0.0223 (12)	0.0310 (13)	0.0200 (14)	0.000	−0.0010 (8)	0.000
C6	0.0220 (12)	0.0256 (13)	0.0269 (14)	0.000	−0.0014 (9)	0.000
C61	0.0186 (12)	0.0424 (15)	0.0289 (15)	0.000	−0.0027 (9)	0.000

Geometric parameters (Å, º)

N1—C2	1.354 (2)	C41—H41B	0.9800
N2—C2	1.336 (3)	C41—H41C	0.9800
N2—H1	0.8800	C5—C6	1.382 (3)
N2—H2	0.8800	C5—H5	0.9500
C2—N3	1.346 (2)	C6—N1	1.338 (3)
N3—C4	1.327 (3)	C6—C61	1.498 (3)
C4—O4	1.349 (2)	C61—H61A	0.9800
C4—C5	1.388 (3)	C61—H61B	0.9800
O4—C41	1.430 (2)	C61—H61C	0.9800
C41—H41A	0.9800
C6—N1—C2	116.03 (18)	O4—C41—H41C	109.5
C2—N2—H1	120.0	H41A—C41—H41C	109.5
C2—N2—H2	120.0	H41B—C41—H41C	109.5
H1—N2—H2	120.0	C6—C5—C4	116.3 (2)
N2—C2—N3	117.26 (17)	C6—C5—H5	121.9
N2—C2—N1	116.88 (18)	C4—C5—H5	121.9
N3—C2—N1	125.9 (2)	N1—C6—C5	122.63 (19)
C4—N3—C2	115.91 (18)	N1—C6—C61	116.93 (18)
N3—C4—O4	112.88 (18)	C5—C6—C61	120.4 (2)
N3—C4—C5	123.3 (2)	C6—C61—H61A	109.5
O4—C4—C5	123.8 (2)	C6—C61—H61B	109.5
C4—O4—C41	117.16 (15)	H61A—C61—H61B	109.5
O4—C41—H41A	109.5	C6—C61—H61C	109.5
O4—C41—H41B	109.5	H61A—C61—H61C	109.5
H41A—C41—H41B	109.5	H61B—C61—H61C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···N1^i	0.88	2.26	3.136 (2)	175
N2—H2···N3^ii	0.88	2.34	3.212 (2)	172

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

(II) 2-Benzylamino-4-benzyloxy-6-methylpyrimidine

Crystal data

C19H19N3O	F(000) = 648
Mr = 305.38	Dx = 1.260 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3667 reflections
a = 5.8932 (2) Å	θ = 2.9–27.5°
b = 18.2849 (7) Å	µ = 0.08 mm^−1
c = 15.1175 (7) Å	T = 120 K
β = 98.704 (2)°	Needle, colourless
V = 1610.25 (11) Å^3	0.26 × 0.18 × 0.10 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	3667 independent reflections
Radiation source: fine-focus sealed X-ray tube	2371 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.093
ϕ scans, and ω scans with κ offsets	θmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	h = −7→7
Tmin = 0.970, Tmax = 0.992	k = −23→21
12340 measured reflections	l = −19→19

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.125	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0662P)^2] where P = (Fo^2 + 2Fc^2)/3
3667 reflections	(Δ/σ)max < 0.001
209 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

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

	x	y	z	Uiso*/Ueq
N1	0.3786 (2)	0.41128 (6)	0.54274 (8)	0.0248 (3)
C2	0.2046 (2)	0.42351 (8)	0.47591 (9)	0.0235 (3)
C21	0.0557 (2)	0.45877 (7)	0.26654 (10)	0.0247 (3)
C22	0.2481 (3)	0.46390 (8)	0.22397 (11)	0.0324 (4)
C23	0.2572 (3)	0.42769 (9)	0.14406 (12)	0.0360 (4)
C24	0.0755 (3)	0.38511 (9)	0.10589 (11)	0.0356 (4)
C25	−0.1153 (3)	0.37827 (9)	0.14836 (11)	0.0352 (4)
C26	−0.1248 (3)	0.41521 (8)	0.22793 (10)	0.0299 (4)
C27	0.0400 (3)	0.50143 (8)	0.35103 (10)	0.0278 (4)
N2	0.2185 (2)	0.48339 (7)	0.42474 (8)	0.0279 (3)
N3	0.0163 (2)	0.38143 (6)	0.45427 (8)	0.0247 (3)
O4	−0.17951 (17)	0.27910 (6)	0.48822 (7)	0.0299 (3)
C4	0.0030 (2)	0.32420 (8)	0.50671 (10)	0.0255 (3)
C41	−0.5105 (3)	0.23401 (8)	0.39309 (10)	0.0281 (4)
C42	−0.7263 (3)	0.24832 (10)	0.34582 (11)	0.0365 (4)
C43	−0.8854 (3)	0.19269 (11)	0.32694 (13)	0.0462 (5)
C44	−0.8316 (3)	0.12265 (11)	0.35528 (13)	0.0456 (5)
C45	−0.6168 (3)	0.10718 (10)	0.40146 (12)	0.0417 (4)
C46	−0.4554 (3)	0.16270 (9)	0.42006 (10)	0.0337 (4)
C47	−0.3399 (3)	0.29512 (8)	0.40894 (10)	0.0288 (4)
C5	0.1674 (3)	0.30720 (8)	0.57925 (10)	0.0279 (4)
C6	0.3570 (2)	0.35210 (8)	0.59406 (10)	0.0252 (3)
C61	0.5501 (3)	0.33671 (9)	0.66774 (10)	0.0307 (4)
H22	0.3752	0.4926	0.2500	0.039*
H23	0.3893	0.4323	0.1154	0.043*
H24	0.0813	0.3606	0.0508	0.043*
H25	−0.2401	0.3483	0.1231	0.042*
H26	−0.2572	0.4106	0.2564	0.036*
H27A	0.0488	0.5543	0.3379	0.033*
H27B	−0.1114	0.4920	0.3696	0.033*
H2	0.3389	0.5122	0.4364	0.034*
H42	−0.7653	0.2967	0.3262	0.044*
H43	−1.0325	0.2030	0.2942	0.055*
H44	−0.9424	0.0848	0.3431	0.055*
H45	−0.5792	0.0586	0.4206	0.050*
H46	−0.3069	0.1519	0.4513	0.040*
H47A	−0.2574	0.3002	0.3569	0.035*
H47B	−0.4200	0.3417	0.4167	0.035*
H5	0.1503	0.2666	0.6169	0.034*
H61A	0.6953	0.3363	0.6436	0.046*
H61B	0.5263	0.2889	0.6943	0.046*
H61C	0.5553	0.3747	0.7137	0.046*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0253 (7)	0.0272 (7)	0.0218 (6)	−0.0004 (5)	0.0033 (5)	−0.0019 (5)
C2	0.0269 (8)	0.0232 (7)	0.0208 (8)	0.0007 (6)	0.0049 (6)	−0.0046 (6)
C21	0.0272 (8)	0.0201 (7)	0.0250 (8)	0.0036 (6)	−0.0016 (6)	0.0030 (6)
C22	0.0288 (8)	0.0305 (8)	0.0371 (9)	−0.0018 (7)	0.0024 (7)	−0.0029 (7)
C23	0.0345 (9)	0.0371 (9)	0.0381 (9)	0.0021 (7)	0.0111 (7)	−0.0019 (8)
C24	0.0447 (10)	0.0342 (9)	0.0273 (9)	0.0017 (7)	0.0031 (7)	−0.0033 (7)
C25	0.0360 (9)	0.0367 (9)	0.0306 (9)	−0.0086 (7)	−0.0027 (7)	−0.0025 (7)
C26	0.0285 (8)	0.0334 (8)	0.0269 (8)	−0.0012 (7)	0.0015 (7)	0.0021 (7)
C27	0.0284 (8)	0.0263 (8)	0.0276 (8)	0.0029 (6)	0.0007 (7)	0.0006 (7)
N2	0.0304 (7)	0.0265 (7)	0.0249 (7)	−0.0035 (5)	−0.0019 (6)	0.0019 (5)
N3	0.0255 (7)	0.0252 (7)	0.0235 (7)	−0.0013 (5)	0.0038 (5)	−0.0032 (5)
O4	0.0292 (6)	0.0350 (6)	0.0240 (6)	−0.0090 (5)	−0.0008 (4)	0.0001 (5)
C4	0.0267 (8)	0.0270 (8)	0.0230 (8)	−0.0047 (6)	0.0049 (6)	−0.0044 (6)
C41	0.0276 (8)	0.0355 (9)	0.0222 (8)	−0.0017 (7)	0.0064 (6)	−0.0065 (7)
C42	0.0305 (9)	0.0447 (10)	0.0341 (9)	0.0032 (7)	0.0038 (7)	−0.0118 (8)
C43	0.0280 (9)	0.0670 (13)	0.0432 (11)	−0.0039 (9)	0.0045 (8)	−0.0251 (10)
C44	0.0406 (11)	0.0589 (13)	0.0395 (10)	−0.0240 (9)	0.0127 (8)	−0.0231 (9)
C45	0.0529 (12)	0.0380 (9)	0.0357 (10)	−0.0135 (8)	0.0113 (9)	−0.0065 (8)
C46	0.0374 (9)	0.0391 (9)	0.0243 (8)	−0.0047 (7)	0.0039 (7)	−0.0025 (7)
C47	0.0277 (8)	0.0327 (9)	0.0252 (8)	−0.0015 (6)	0.0018 (6)	−0.0024 (7)
C5	0.0328 (9)	0.0287 (8)	0.0221 (8)	−0.0039 (6)	0.0036 (7)	0.0018 (6)
C6	0.0284 (8)	0.0276 (8)	0.0202 (7)	0.0001 (6)	0.0057 (6)	−0.0028 (6)
C61	0.0300 (8)	0.0360 (9)	0.0254 (8)	−0.0053 (7)	0.0017 (7)	0.0031 (7)

Geometric parameters (Å, º)

N1—C2	1.3447 (19)	C26—H26	0.95
C2—N3	1.3493 (18)	C27—H27A	0.99
N3—C4	1.3223 (19)	C27—H27B	0.99
C4—C5	1.384 (2)	N2—H2	0.88
C5—C6	1.377 (2)	C41—C42	1.386 (2)
C6—N1	1.3486 (19)	C41—C46	1.390 (2)
C2—N2	1.3501 (19)	C41—C47	1.498 (2)
N2—C27	1.450 (2)	C42—C43	1.383 (2)
C4—O4	1.3505 (18)	C42—H42	0.95
O4—C47	1.4398 (19)	C43—C44	1.372 (3)
C6—C61	1.494 (2)	C43—H43	0.95
C21—C26	1.385 (2)	C44—C45	1.379 (3)
C21—C22	1.389 (2)	C44—H44	0.95
C21—C27	1.511 (2)	C45—C46	1.391 (2)
C22—C23	1.386 (2)	C45—H45	0.95
C22—H22	0.95	C46—H46	0.95
C23—C24	1.378 (2)	C47—H47A	0.99
C23—H23	0.95	C47—H47B	0.99
C24—C25	1.382 (2)	C5—H5	0.95
C24—H24	0.95	C61—H61A	0.98
C25—C26	1.388 (2)	C61—H61B	0.98
C25—H25	0.95	C61—H61C	0.98
C2—N1—C6	115.97 (12)	C42—C41—C46	118.93 (15)
N1—C2—N3	126.36 (13)	C42—C41—C47	118.87 (15)
N1—C2—N2	117.39 (13)	C46—C41—C47	122.11 (14)
N3—C2—N2	116.25 (13)	C43—C42—C41	120.51 (17)
C26—C21—C22	118.18 (14)	C43—C42—H42	119.7
C26—C21—C27	120.77 (13)	C41—C42—H42	119.7
C22—C21—C27	121.02 (13)	C44—C43—C42	120.30 (17)
C23—C22—C21	120.88 (15)	C44—C43—H43	119.9
C23—C22—H22	119.6	C42—C43—H43	119.9
C21—C22—H22	119.6	C43—C44—C45	120.03 (16)
C24—C23—C22	120.34 (15)	C43—C44—H44	120.0
C24—C23—H23	119.8	C45—C44—H44	120.0
C22—C23—H23	119.8	C44—C45—C46	120.00 (17)
C23—C24—C25	119.46 (15)	C44—C45—H45	120.0
C23—C24—H24	120.3	C46—C45—H45	120.0
C25—C24—H24	120.3	C41—C46—C45	120.21 (16)
C24—C25—C26	120.04 (15)	C41—C46—H46	119.9
C24—C25—H25	120.0	C45—C46—H46	119.9
C26—C25—H25	120.0	O4—C47—C41	108.76 (12)
C21—C26—C25	121.07 (14)	O4—C47—H47A	109.9
C21—C26—H26	119.5	C41—C47—H47A	109.9
C25—C26—H26	119.5	O4—C47—H47B	109.9
N2—C27—C21	113.70 (12)	C41—C47—H47B	109.9
N2—C27—H27A	108.8	H47A—C47—H47B	108.3
C21—C27—H27A	108.8	C6—C5—C4	116.62 (14)
N2—C27—H27B	108.8	C6—C5—H5	121.7
C21—C27—H27B	108.8	C4—C5—H5	121.7
H27A—C27—H27B	107.7	N1—C6—C5	121.99 (14)
C2—N2—C27	121.68 (13)	N1—C6—C61	116.91 (13)
C2—N2—H2	119.2	C5—C6—C61	121.10 (14)
C27—N2—H2	119.2	C6—C61—H61A	109.5
C4—N3—C2	115.30 (12)	C6—C61—H61B	109.5
C4—O4—C47	116.74 (11)	H61A—C61—H61B	109.5
N3—C4—O4	118.49 (13)	C6—C61—H61C	109.5
N3—C4—C5	123.68 (14)	H61A—C61—H61C	109.5
O4—C4—C5	117.82 (13)	H61B—C61—H61C	109.5
C6—N1—C2—N3	−2.0 (2)	N3—C4—O4—C47	3.38 (19)
C6—N1—C2—N2	178.36 (12)	C47—O4—C4—C5	−175.87 (13)
C26—C21—C22—C23	1.4 (2)	C46—C41—C42—C43	0.9 (2)
C27—C21—C22—C23	−176.65 (14)	C47—C41—C42—C43	177.54 (14)
C21—C22—C23—C24	−0.8 (2)	C41—C42—C43—C44	0.4 (3)
C22—C23—C24—C25	−0.5 (2)	C42—C43—C44—C45	−1.1 (3)
C23—C24—C25—C26	1.2 (2)	C43—C44—C45—C46	0.6 (3)
C22—C21—C26—C25	−0.7 (2)	C42—C41—C46—C45	−1.4 (2)
C27—C21—C26—C25	177.32 (14)	C47—C41—C46—C45	−177.95 (14)
C24—C25—C26—C21	−0.6 (2)	C44—C45—C46—C41	0.7 (2)
C26—C21—C27—N2	121.32 (15)	C4—O4—C47—C41	172.35 (12)
N3—C2—N2—C27	0.31 (19)	O4—C47—C41—C42	154.41 (13)
N1—C2—N2—C27	179.97 (12)	C46—C41—C47—O4	−29.09 (19)
C2—N2—C27—C21	−80.49 (17)	N3—C4—C5—C6	−2.2 (2)
N2—C27—C21—C22	−60.71 (18)	O4—C4—C5—C6	177.00 (12)
N1—C2—N3—C4	2.2 (2)	C2—N1—C6—C5	−0.42 (19)
N2—C2—N3—C4	−178.20 (12)	C2—N1—C6—C61	178.98 (12)
C2—N3—C4—O4	−179.11 (11)	C4—C5—C6—N1	2.4 (2)
C2—N3—C4—C5	0.1 (2)	C4—C5—C6—C61	−177.02 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N1^i	0.88	2.16	3.039 (2)	176

Symmetry code: (i) −x+1, −y+1, −z+1.

(III) 4-Benzylamino-2,6-bis(benzyloxy)pyrimidine

Crystal data

C25H23N3O2	F(000) = 840
Mr = 397.46	Dx = 1.273 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4691 reflections
a = 5.6056 (2) Å	θ = 3.0–27.5°
b = 18.2446 (5) Å	µ = 0.08 mm^−1
c = 20.6480 (8) Å	T = 120 K
β = 100.965 (1)°	Block, colourless
V = 2073.16 (12) Å^3	0.50 × 0.30 × 0.15 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	4691 independent reflections
Radiation source: fine-focus sealed X-ray tube	2822 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.076
ϕ scans, and ω scans with κ offsets	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (DENZO–SMN; Otwinowski & Minor, 1997)	h = −7→6
Tmin = 0.950, Tmax = 0.987	k = −23→18
16019 measured reflections	l = −26→26

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.131	H-atom parameters constrained
S = 0.96	w = 1/[σ^2(Fo^2) + (0.0684P)^2] where P = (Fo^2 + 2Fc^2)/3
4691 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

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

	x	y	z	Uiso*/Ueq
N1	1.0799 (2)	0.40310 (8)	0.62780 (7)	0.0219 (4)
C2	0.8732 (3)	0.40173 (10)	0.58335 (8)	0.0212 (4)
C21	0.6951 (3)	0.21091 (10)	0.58460 (9)	0.0241 (4)
C22	0.5821 (3)	0.17710 (11)	0.63056 (9)	0.0309 (5)
C23	0.4128 (4)	0.12225 (12)	0.61258 (10)	0.0364 (5)
C24	0.3545 (3)	0.10049 (11)	0.54768 (10)	0.0348 (5)
C25	0.4638 (4)	0.13319 (12)	0.50108 (10)	0.0408 (5)
C26	0.6342 (4)	0.18797 (11)	0.51939 (10)	0.0369 (5)
C27	0.8704 (3)	0.27252 (10)	0.60378 (9)	0.0270 (4)
O2	0.7589 (2)	0.33668 (7)	0.57016 (6)	0.0253 (3)
N3	0.7552 (2)	0.45599 (8)	0.54943 (7)	0.0213 (3)
N4	0.7413 (2)	0.57865 (8)	0.52500 (7)	0.0221 (4)
C4	0.8585 (3)	0.52300 (10)	0.56023 (8)	0.0207 (4)
C41	0.7785 (3)	0.68374 (10)	0.60319 (9)	0.0226 (4)
C42	0.6246 (4)	0.64959 (12)	0.63845 (10)	0.0387 (5)
C43	0.5943 (4)	0.67636 (12)	0.69907 (11)	0.0431 (6)
C44	0.7198 (3)	0.73721 (11)	0.72561 (10)	0.0331 (5)
C45	0.8752 (4)	0.77118 (12)	0.69155 (10)	0.0408 (6)
C46	0.9047 (4)	0.74430 (12)	0.63086 (10)	0.0369 (5)
C47	0.8116 (3)	0.65442 (10)	0.53648 (9)	0.0241 (4)
C5	1.0748 (3)	0.53260 (10)	0.60609 (8)	0.0217 (4)
C6	1.1744 (3)	0.47034 (10)	0.63757 (8)	0.0219 (4)
C61	1.6809 (3)	0.44110 (10)	0.77412 (9)	0.0232 (4)
C62	1.7009 (3)	0.41495 (11)	0.83814 (9)	0.0279 (4)
C63	1.8945 (3)	0.43636 (11)	0.88699 (10)	0.0321 (5)
C64	2.0670 (3)	0.48398 (11)	0.87229 (10)	0.0328 (5)
C65	2.0476 (3)	0.51062 (11)	0.80854 (10)	0.0325 (5)
C66	1.8547 (3)	0.48915 (11)	0.75981 (9)	0.0282 (5)
C67	1.4741 (3)	0.41581 (10)	0.72120 (9)	0.0254 (4)
O6	1.3804 (2)	0.47949 (7)	0.68340 (6)	0.0260 (3)
H22	0.6217	0.1919	0.6754	0.037*
H23	0.3369	0.0997	0.6448	0.044*
H24	0.2383	0.0627	0.5351	0.042*
H25	0.4226	0.1183	0.4563	0.049*
H26	0.7103	0.2101	0.4870	0.044*
H27A	0.9010	0.2800	0.6521	0.032*
H27B	1.0269	0.2618	0.5902	0.032*
H4	0.6162	0.5684	0.4936	0.027*
H42	0.5381	0.6071	0.6209	0.046*
H43	0.4860	0.6525	0.7224	0.052*
H44	0.6990	0.7556	0.7672	0.040*
H45	0.9631	0.8133	0.7096	0.049*
H46	1.0142	0.7681	0.6079	0.044*
H47A	0.7144	0.6848	0.5014	0.029*
H47B	0.9845	0.6597	0.5330	0.029*
H5	1.1482	0.5794	0.6149	0.026*
H62	1.5817	0.3823	0.8486	0.033*
H63	1.9077	0.4181	0.9306	0.039*
H64	2.1993	0.4986	0.9057	0.039*
H65	2.1664	0.5436	0.7983	0.039*
H66	1.8418	0.5076	0.7162	0.034*
H67A	1.5324	0.3792	0.6924	0.031*
H67B	1.3454	0.3930	0.7413	0.031*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0233 (8)	0.0220 (9)	0.0196 (8)	−0.0025 (6)	0.0022 (6)	−0.0002 (7)
C2	0.0234 (9)	0.0219 (11)	0.0183 (9)	−0.0022 (8)	0.0041 (7)	−0.0021 (8)
C21	0.0251 (9)	0.0222 (11)	0.0240 (10)	0.0016 (8)	0.0020 (7)	0.0013 (8)
C22	0.0343 (10)	0.0342 (13)	0.0235 (10)	−0.0032 (9)	0.0038 (8)	0.0020 (9)
C23	0.0379 (11)	0.0399 (14)	0.0318 (12)	−0.0094 (10)	0.0074 (9)	0.0095 (10)
C24	0.0341 (11)	0.0298 (13)	0.0368 (12)	−0.0104 (9)	−0.0027 (9)	0.0053 (10)
C25	0.0557 (13)	0.0395 (14)	0.0258 (11)	−0.0172 (11)	0.0047 (9)	−0.0061 (10)
C26	0.0477 (12)	0.0355 (13)	0.0299 (11)	−0.0157 (10)	0.0132 (9)	−0.0014 (10)
C27	0.0309 (10)	0.0222 (11)	0.0254 (10)	−0.0002 (8)	−0.0003 (8)	0.0041 (8)
O2	0.0276 (6)	0.0174 (7)	0.0279 (7)	−0.0024 (5)	−0.0024 (5)	0.0011 (6)
N3	0.0233 (7)	0.0193 (9)	0.0205 (8)	−0.0029 (6)	0.0018 (6)	−0.0007 (7)
N4	0.0256 (8)	0.0197 (9)	0.0182 (8)	−0.0026 (6)	−0.0033 (6)	−0.0008 (6)
C4	0.0235 (9)	0.0238 (11)	0.0156 (9)	−0.0010 (8)	0.0056 (7)	−0.0009 (8)
C41	0.0212 (8)	0.0214 (11)	0.0245 (10)	0.0021 (7)	0.0023 (7)	0.0010 (8)
C42	0.0360 (11)	0.0393 (14)	0.0446 (13)	−0.0150 (9)	0.0175 (9)	−0.0167 (11)
C43	0.0460 (12)	0.0454 (15)	0.0452 (13)	−0.0160 (10)	0.0270 (10)	−0.0144 (11)
C44	0.0412 (11)	0.0328 (13)	0.0266 (11)	−0.0013 (9)	0.0101 (9)	−0.0066 (9)
C45	0.0507 (13)	0.0357 (14)	0.0376 (13)	−0.0175 (10)	0.0124 (10)	−0.0142 (10)
C46	0.0460 (12)	0.0350 (13)	0.0332 (12)	−0.0182 (10)	0.0163 (9)	−0.0051 (10)
C47	0.0285 (9)	0.0208 (11)	0.0221 (10)	−0.0014 (8)	0.0030 (7)	0.0004 (8)
C5	0.0229 (9)	0.0204 (11)	0.0219 (9)	−0.0029 (7)	0.0044 (7)	−0.0008 (8)
C6	0.0215 (9)	0.0263 (11)	0.0174 (9)	−0.0024 (8)	0.0026 (7)	−0.0010 (8)
C61	0.0231 (9)	0.0209 (11)	0.0244 (10)	0.0052 (8)	0.0015 (7)	−0.0029 (8)
C62	0.0287 (10)	0.0261 (12)	0.0278 (11)	0.0029 (8)	0.0029 (8)	0.0025 (8)
C63	0.0376 (11)	0.0278 (12)	0.0269 (11)	0.0082 (9)	−0.0040 (8)	−0.0005 (9)
C64	0.0263 (10)	0.0318 (13)	0.0353 (12)	0.0056 (9)	−0.0068 (8)	−0.0055 (9)
C65	0.0252 (10)	0.0354 (13)	0.0372 (12)	−0.0023 (8)	0.0062 (8)	−0.0062 (10)
C66	0.0258 (9)	0.0330 (12)	0.0258 (10)	0.0024 (8)	0.0052 (8)	−0.0019 (9)
C67	0.0272 (10)	0.0226 (11)	0.0245 (10)	0.0015 (8)	−0.0002 (7)	0.0025 (8)
O6	0.0241 (6)	0.0248 (8)	0.0254 (7)	−0.0035 (5)	−0.0048 (5)	0.0023 (6)

Geometric parameters (Å, º)

N1—C2	1.335 (2)	C41—C42	1.379 (3)
C2—N3	1.316 (2)	C41—C47	1.522 (3)
N3—C4	1.353 (2)	C42—C43	1.384 (3)
C4—C5	1.400 (2)	C42—H42	0.95
C5—C6	1.374 (2)	C43—C44	1.371 (3)
C6—N1	1.336 (2)	C43—H43	0.95
C2—O2	1.352 (2)	C44—C45	1.368 (3)
O2—C27	1.441 (2)	C44—H44	0.95
C4—N4	1.345 (2)	C45—C46	1.384 (3)
N4—C47	1.445 (2)	C45—H45	0.95
C6—O6	1.357 (2)	C46—H46	0.95
O6—C67	1.442 (2)	C47—H47A	0.99
C21—C22	1.382 (3)	C47—H47B	0.99
C21—C26	1.389 (3)	C5—H5	0.95
C21—C27	1.496 (3)	C61—C66	1.384 (3)
C22—C23	1.380 (3)	C61—C62	1.390 (2)
C22—H22	0.95	C61—C67	1.506 (2)
C23—C24	1.376 (3)	C62—C63	1.389 (3)
C23—H23	0.95	C62—H62	0.95
C24—C25	1.372 (3)	C63—C64	1.376 (3)
C24—H24	0.95	C63—H63	0.95
C25—C26	1.384 (3)	C64—C65	1.388 (3)
C25—H25	0.95	C64—H64	0.95
C26—H26	0.95	C65—C66	1.386 (3)
C27—H27A	0.99	C65—H65	0.95
C27—H27B	0.99	C66—H66	0.95
N4—H4	0.88	C67—H67A	0.99
C41—C46	1.376 (3)	C67—H67B	0.99
C2—N1—C6	112.86 (15)	C45—C44—H44	120.3
N3—C2—N1	129.39 (17)	C43—C44—H44	120.3
N3—C2—O2	112.48 (14)	C44—C45—C46	120.15 (19)
N1—C2—O2	118.12 (15)	C44—C45—H45	119.9
C22—C21—C26	118.08 (17)	C46—C45—H45	119.9
C22—C21—C27	121.15 (17)	C41—C46—C45	121.32 (18)
C26—C21—C27	120.72 (17)	C41—C46—H46	119.3
C23—C22—C21	121.34 (18)	C45—C46—H46	119.3
C23—C22—H22	119.3	N4—C47—C41	114.11 (15)
C21—C22—H22	119.3	N4—C47—H47A	108.7
C24—C23—C22	119.65 (18)	C41—C47—H47A	108.7
C24—C23—H23	120.2	N4—C47—H47B	108.7
C22—C23—H23	120.2	C41—C47—H47B	108.7
C25—C24—C23	120.18 (19)	H47A—C47—H47B	107.6
C25—C24—H24	119.9	C6—C5—C4	116.01 (16)
C23—C24—H24	119.9	C6—C5—H5	122.0
C24—C25—C26	119.96 (19)	C4—C5—H5	122.0
C24—C25—H25	120.0	N1—C6—O6	118.59 (15)
C26—C25—H25	120.0	N1—C6—C5	125.02 (16)
C25—C26—C21	120.78 (18)	O6—C6—C5	116.35 (16)
C25—C26—H26	119.6	C66—C61—C62	119.21 (16)
C21—C26—H26	119.6	C66—C61—C67	121.00 (16)
O2—C27—C21	106.25 (14)	C62—C61—C67	119.79 (16)
O2—C27—H27A	110.5	C63—C62—C61	120.31 (18)
C21—C27—H27A	110.5	C63—C62—H62	119.8
O2—C27—H27B	110.5	C61—C62—H62	119.8
C21—C27—H27B	110.5	C64—C63—C62	120.12 (18)
H27A—C27—H27B	108.7	C64—C63—H63	119.9
C2—O2—C27	118.07 (13)	C62—C63—H63	119.9
C2—N3—C4	115.86 (15)	C63—C64—C65	119.90 (17)
C4—N4—C47	122.92 (14)	C63—C64—H64	120.0
C4—N4—H4	118.5	C65—C64—H64	120.0
C47—N4—H4	118.5	C66—C65—C64	119.96 (19)
N4—C4—N3	116.32 (15)	C66—C65—H65	120.0
N4—C4—C5	122.84 (16)	C64—C65—H65	120.0
N3—C4—C5	120.85 (16)	C61—C66—C65	120.51 (18)
C46—C41—C42	117.86 (17)	C61—C66—H66	119.7
C46—C41—C47	121.11 (16)	C65—C66—H66	119.7
C42—C41—C47	121.02 (16)	O6—C67—C61	107.27 (14)
C41—C42—C43	120.99 (19)	O6—C67—H67A	110.3
C41—C42—H42	119.5	C61—C67—H67A	110.3
C43—C42—H42	119.5	O6—C67—H67B	110.3
C44—C43—C42	120.35 (19)	C61—C67—H67B	110.3
C44—C43—H43	119.8	H67A—C67—H67B	108.5
C42—C43—H43	119.8	C6—O6—C67	116.91 (13)
C45—C44—C43	119.32 (18)
C6—N1—C2—N3	−0.2 (3)	C42—C43—C44—C45	0.0 (3)
C6—N1—C2—O2	−179.01 (14)	C43—C44—C45—C46	0.1 (3)
C26—C21—C22—C23	−0.2 (3)	C42—C41—C46—C45	−1.3 (3)
C27—C21—C22—C23	177.32 (18)	C47—C41—C46—C45	180.00 (19)
C21—C22—C23—C24	0.0 (3)	C44—C45—C46—C41	0.5 (3)
C22—C23—C24—C25	−0.1 (3)	C46—C41—C47—N4	158.68 (17)
C23—C24—C25—C26	0.3 (3)	N4—C4—C5—C6	−179.18 (16)
C24—C25—C26—C21	−0.5 (3)	N3—C4—C5—C6	1.2 (2)
C22—C21—C26—C25	0.5 (3)	C2—N1—C6—O6	177.68 (14)
C27—C21—C26—C25	−177.08 (19)	C2—N1—C6—C5	−0.1 (2)
C26—C21—C27—O2	63.4 (2)	C4—C5—C6—N1	−0.5 (3)
N3—C2—O2—C27	179.54 (14)	C4—C5—C6—O6	−178.24 (14)
N1—C2—O2—C27	−1.4 (2)	C66—C61—C62—C63	−0.6 (3)
C2—O2—C27—C21	174.90 (15)	C67—C61—C62—C63	178.28 (17)
O2—C27—C21—C22	−114.06 (18)	C61—C62—C63—C64	0.3 (3)
N1—C2—N3—C4	0.9 (3)	C62—C63—C64—C65	0.0 (3)
O2—C2—N3—C4	179.79 (14)	C63—C64—C65—C66	−0.1 (3)
C47—N4—C4—N3	172.32 (14)	C62—C61—C66—C65	0.5 (3)
C5—C4—N4—C47	−7.3 (2)	C67—C61—C66—C65	−178.38 (17)
C4—N4—C47—C41	−65.7 (2)	C64—C65—C66—C61	−0.1 (3)
N4—C47—C41—C42	−20.0 (2)	C66—C61—C67—O6	−44.9 (2)
C2—N3—C4—N4	178.97 (15)	N1—C6—O6—C67	−3.6 (2)
C2—N3—C4—C5	−1.4 (2)	C6—O6—C67—C61	−172.75 (14)
C46—C41—C42—C43	1.4 (3)	O6—C67—C61—C62	136.29 (16)
C47—C41—C42—C43	−179.89 (19)	C5—C6—O6—C67	174.31 (15)
C41—C42—C43—C44	−0.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N3^i	0.88	2.15	2.980 (2)	157

Symmetry code: (i) −x+1, −y+1, −z+1.