Supramolecular structures of N⁴-substituted 2,4-diamino-6-benzyloxy-5-nitrosopyrimidines

The molecular and supramolecular structures of eight N⁴-substituted 2,4-diamino-6-benzyloxy-5-nitrosopyrimidines are discussed, along with one analogue containing no nitroso substituent. The nitroso derivatives all exhibit polarized molecular-electronic structures leading to extensive charge-assisted hydrogen bonding between the molecules. The intermolecular interactions include hard hydrogen bonds of N—H...O and N—H...N types, together with O—H...O and O—H...N types in the monohydrate of 2-amino-6-benzyloxy-4-piperidino-5-nitrosopyrimidine, soft hydrogen bonds of C—H...O, C—H...π(arene) and N—H...π(arene) types and aromatic π...π stacking interactions. The predominant supramolecular structure types take the form of chains and sheets, but no two of the structures determined here exhibit the same combination of hydrogen-bond types.

S1. Comment

In full text version

S2. Experimental

In full text version

S3. Refinement

In full text version

Computing details

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

Figures

In full text version

(1) 2-Amino-6-benzyloxy-4-(N-methylamino)-5-nitrosopyrimidine

Crystal data

C12H13N5O2	F(000) = 544
Mr = 259.27	Dx = 1.402 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1649 reflections
a = 7.1122 (2) Å	θ = 3.0–27.5°
b = 7.3873 (2) Å	µ = 0.10 mm^−1
c = 23.3867 (7) Å	T = 120 K
V = 1228.74 (6) Å^3	Plate, pink
Z = 4	0.30 × 0.14 × 0.07 mm

Data collection

Kappa-CCD diffractometer	1649 independent reflections
Radiation source: fine-focus sealed X-ray tube	1323 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.060
ϕ scans, and ω scans with κ offsets	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −9→7
Tmin = 0.954, Tmax = 0.994	k = −8→9
6981 measured reflections	l = −30→30

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.090	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0467P)^2] where P = (Fo^2 + 2Fc^2)/3
1649 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.18 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
N1	0.7669 (3)	1.1531 (2)	0.13328 (8)	0.0226 (4)
C2	0.8858 (3)	1.2910 (3)	0.14977 (10)	0.0220 (5)
N2	0.8267 (3)	1.4559 (3)	0.13741 (9)	0.0316 (5)
N3	1.0523 (2)	1.2758 (2)	0.17588 (8)	0.0226 (4)
C4	1.1051 (3)	1.1086 (3)	0.19092 (9)	0.0198 (5)
N4	1.2650 (3)	1.0868 (2)	0.21909 (8)	0.0248 (4)
C41	1.3894 (3)	1.2361 (3)	0.23419 (11)	0.0303 (6)
C5	0.9949 (3)	0.9511 (3)	0.17556 (9)	0.0193 (5)
N5	1.0382 (3)	0.7757 (2)	0.18412 (8)	0.0235 (4)
O5	1.1890 (2)	0.7408 (2)	0.21219 (7)	0.0271 (4)
C6	0.8244 (3)	0.9904 (3)	0.14496 (9)	0.0194 (5)
C61	0.5036 (3)	0.7082 (3)	0.06605 (9)	0.0224 (5)
C62	0.3886 (3)	0.5793 (3)	0.09145 (10)	0.0256 (5)
C63	0.3519 (3)	0.4165 (3)	0.06323 (11)	0.0294 (6)
C64	0.4296 (3)	0.3826 (3)	0.01079 (10)	0.0320 (6)
C65	0.5449 (3)	0.5104 (3)	−0.01465 (11)	0.0311 (6)
C66	0.5817 (3)	0.6723 (3)	0.01291 (10)	0.0271 (6)
C67	0.5514 (3)	0.8825 (3)	0.09596 (10)	0.0273 (5)
O6	0.7229 (2)	0.84726 (19)	0.12848 (6)	0.0239 (4)
H2A	0.8962	1.5503	0.1464	0.038*
H2B	0.7178	1.4714	0.1202	0.038*
H4	1.2978	0.9765	0.2292	0.030*
H41A	1.4801	1.2559	0.2033	0.045*
H41B	1.4569	1.2066	0.2695	0.045*
H41C	1.3150	1.3462	0.2400	0.045*
H62	0.3350	0.6019	0.1280	0.031*
H63	0.2725	0.3288	0.0805	0.035*
H64	0.4045	0.2714	−0.0082	0.038*
H65	0.5989	0.4868	−0.0511	0.037*
H66	0.6610	0.7595	−0.0047	0.033*
H67A	0.5725	0.9804	0.0678	0.033*
H67B	0.4481	0.9190	0.1219	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0226 (10)	0.0180 (9)	0.0272 (10)	0.0025 (8)	−0.0019 (9)	−0.0012 (8)
C2	0.0255 (11)	0.0177 (11)	0.0227 (12)	0.0016 (9)	0.0014 (10)	−0.0019 (10)
N2	0.0326 (12)	0.0164 (10)	0.0458 (13)	0.0013 (8)	−0.0126 (10)	−0.0008 (9)
N3	0.0227 (10)	0.0190 (9)	0.0262 (10)	−0.0009 (8)	−0.0021 (8)	−0.0010 (8)
C4	0.0190 (11)	0.0212 (12)	0.0192 (11)	−0.0002 (9)	0.0005 (9)	−0.0031 (9)
N4	0.0214 (10)	0.0229 (10)	0.0300 (11)	0.0015 (8)	−0.0030 (9)	−0.0020 (8)
C41	0.0218 (12)	0.0347 (14)	0.0342 (14)	−0.0071 (11)	−0.0027 (10)	−0.0063 (11)
C5	0.0201 (11)	0.0165 (11)	0.0214 (11)	0.0010 (9)	−0.0003 (10)	−0.0009 (9)
N5	0.0210 (10)	0.0255 (10)	0.0239 (10)	0.0027 (8)	−0.0020 (8)	0.0004 (8)
O5	0.0233 (8)	0.0268 (9)	0.0311 (9)	0.0058 (7)	−0.0063 (7)	0.0002 (7)
C6	0.0201 (11)	0.0174 (11)	0.0208 (11)	0.0006 (9)	−0.0005 (9)	−0.0026 (9)
C61	0.0189 (11)	0.0210 (12)	0.0273 (13)	0.0026 (9)	−0.0079 (10)	−0.0004 (9)
C62	0.0247 (13)	0.0278 (12)	0.0245 (12)	0.0016 (10)	−0.0005 (10)	0.0005 (10)
C63	0.0289 (13)	0.0264 (13)	0.0329 (14)	−0.0079 (10)	−0.0030 (12)	0.0048 (11)
C64	0.0381 (15)	0.0242 (13)	0.0338 (14)	−0.0017 (11)	−0.0063 (12)	−0.0060 (11)
C65	0.0308 (14)	0.0378 (14)	0.0245 (12)	0.0026 (11)	0.0011 (11)	−0.0044 (11)
C66	0.0221 (12)	0.0302 (14)	0.0290 (13)	−0.0037 (10)	−0.0014 (11)	0.0039 (10)
C67	0.0228 (13)	0.0226 (12)	0.0365 (13)	0.0034 (9)	−0.0090 (11)	−0.0042 (10)
O6	0.0229 (8)	0.0173 (8)	0.0315 (9)	0.0004 (6)	−0.0101 (7)	−0.0012 (7)

Geometric parameters (Å, º)

N1—C6	1.299 (3)	C6—O6	1.337 (2)
N1—C2	1.379 (3)	C61—C66	1.387 (3)
C2—N2	1.320 (3)	C61—C62	1.388 (3)
C2—N3	1.337 (3)	C61—C67	1.504 (3)
N2—H2A	0.88	C62—C63	1.396 (3)
N2—H2B	0.88	C62—H62	0.95
N3—C4	1.338 (3)	C63—C64	1.368 (3)
C4—N4	1.324 (3)	C63—H63	0.95
C4—C5	1.448 (3)	C64—C65	1.385 (3)
N4—C41	1.457 (3)	C64—H64	0.95
N4—H4	0.88	C65—C66	1.384 (3)
C41—H41A	0.98	C65—H65	0.95
C41—H41B	0.98	C66—H66	0.95
C41—H41C	0.98	C67—O6	1.461 (3)
C5—N5	1.347 (3)	C67—H67A	0.99
C5—C6	1.438 (3)	C67—H67B	0.99
N5—O5	1.283 (2)
C6—N1—C2	115.56 (18)	O6—C6—C5	116.07 (18)
N2—C2—N3	117.4 (2)	C66—C61—C62	119.2 (2)
N2—C2—N1	115.1 (2)	C66—C61—C67	119.3 (2)
N3—C2—N1	127.51 (18)	C62—C61—C67	121.4 (2)
C2—N2—H2A	120.0	C61—C62—C63	119.9 (2)
C2—N2—H2B	120.0	C61—C62—H62	120.0
H2A—N2—H2B	120.0	C63—C62—H62	120.0
C2—N3—C4	116.51 (18)	C64—C63—C62	120.4 (2)
N4—C4—N3	118.95 (19)	C64—C63—H63	119.8
N4—C4—C5	119.37 (19)	C62—C63—H63	119.8
N3—C4—C5	121.66 (19)	C63—C64—C65	119.9 (2)
C4—N4—C41	123.37 (18)	C63—C64—H64	120.0
C4—N4—H4	118.3	C65—C64—H64	120.0
C41—N4—H4	118.3	C66—C65—C64	120.1 (2)
N4—C41—H41A	109.5	C66—C65—H65	120.0
N4—C41—H41B	109.5	C64—C65—H65	120.0
H41A—C41—H41B	109.5	C65—C66—C61	120.5 (2)
N4—C41—H41C	109.5	C65—C66—H66	119.8
H41A—C41—H41C	109.5	C61—C66—H66	119.8
H41B—C41—H41C	109.5	O6—C67—C61	106.16 (18)
N5—C5—C6	117.45 (19)	O6—C67—H67A	110.5
N5—C5—C4	127.8 (2)	C61—C67—H67A	110.5
C6—C5—C4	114.69 (18)	O6—C67—H67B	110.5
O5—N5—C5	117.39 (19)	C61—C67—H67B	110.5
N1—C6—O6	120.08 (18)	H67A—C67—H67B	108.7
N1—C6—C5	123.85 (18)	C6—O6—C67	117.40 (16)
C6—N1—C2—N2	179.6 (2)	C4—C5—C6—N1	−2.4 (3)
C6—N1—C2—N3	0.4 (3)	N5—C5—C6—O6	0.9 (3)
N2—C2—N3—C4	176.4 (2)	C4—C5—C6—O6	177.79 (18)
N1—C2—N3—C4	−4.4 (3)	C66—C61—C62—C63	−0.5 (3)
C2—N3—C4—N4	−177.14 (19)	C67—C61—C62—C63	−178.0 (2)
C2—N3—C4—C5	4.9 (3)	C61—C62—C63—C64	0.4 (4)
N3—C4—N4—C41	−0.8 (3)	C62—C63—C64—C65	−0.2 (4)
C5—C4—N4—C41	177.20 (19)	C63—C64—C65—C66	0.0 (3)
N4—C4—C5—N5	−3.3 (3)	C64—C65—C66—C61	−0.1 (3)
N3—C4—C5—N5	174.6 (2)	C62—C61—C66—C65	0.3 (3)
N4—C4—C5—C6	−179.84 (19)	C67—C61—C66—C65	177.9 (2)
N3—C4—C5—C6	−1.9 (3)	C66—C61—C67—O6	−87.4 (2)
C6—C5—N5—O5	−178.96 (17)	C62—C61—C67—O6	90.2 (2)
C4—C5—N5—O5	4.6 (3)	N1—C6—O6—C67	1.8 (3)
C2—N1—C6—O6	−177.08 (19)	C5—C6—O6—C67	−178.41 (18)
C2—N1—C6—C5	3.1 (3)	C61—C67—O6—C6	160.73 (19)
N5—C5—C6—N1	−179.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O5	0.88	1.95	2.618 (2)	132
N2—H2A···N5^i	0.88	2.14	3.006 (3)	169
N2—H2B···Cg1^i	0.88	2.68	3.516 (2)	160
C62—H62···O5^ii	0.95	2.45	3.379 (3)	165
C66—H66···Cg1^iii	0.95	2.73	3.647 (2)	163

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

(2) 2-Amino-6-benzyloxy-4-(N-butylamino)-5-nitrosopyrimidine

Crystal data

C15H19N5O2	F(000) = 640
Mr = 301.35	Dx = 1.325 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3424 reflections
a = 7.6146 (2) Å	θ = 3.0–27.5°
b = 13.7686 (4) Å	µ = 0.09 mm^−1
c = 16.1215 (5) Å	T = 120 K
β = 116.6180 (15)°	Block, blue
V = 1511.08 (8) Å^3	0.35 × 0.20 × 0.15 mm
Z = 4

Data collection

Kappa-CCD diffractometer	3424 independent reflections
Radiation source: fine-focus sealed X-ray tube	2616 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.074
ϕ scans, and ω scans with κ offsets	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −9→8
Tmin = 0.966, Tmax = 0.988	k = −17→17
12361 measured reflections	l = −19→20

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0624P)^2 + 0.2767P] where P = (Fo^2 + 2Fc^2)/3
3424 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

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

	x	y	z	Uiso*/Ueq
N1	0.49974 (16)	0.21875 (8)	0.22659 (7)	0.0202 (3)
C2	0.32244 (19)	0.17163 (9)	0.19166 (9)	0.0190 (3)
N2	0.33078 (17)	0.07829 (8)	0.21439 (8)	0.0246 (3)
N3	0.14484 (16)	0.20783 (8)	0.13701 (8)	0.0198 (3)
C4	0.13639 (18)	0.30251 (10)	0.11613 (9)	0.0180 (3)
C41	−0.22046 (19)	0.28505 (10)	0.02664 (10)	0.0249 (3)
C42	−0.39648 (19)	0.35122 (10)	−0.00866 (10)	0.0248 (3)
C43	−0.58963 (19)	0.29642 (11)	−0.04435 (10)	0.0257 (3)
C44	−0.7649 (2)	0.36379 (12)	−0.08310 (11)	0.0304 (4)
N4	−0.03742 (16)	0.34023 (8)	0.06105 (8)	0.0210 (3)
C5	0.31037 (18)	0.36262 (9)	0.15438 (9)	0.0177 (3)
N5	0.32012 (16)	0.45998 (8)	0.14812 (8)	0.0209 (3)
O5	0.16146 (13)	0.50492 (7)	0.09819 (7)	0.0248 (2)
C6	0.48887 (19)	0.31171 (10)	0.20825 (9)	0.0184 (3)
O6	0.65323 (13)	0.36451 (7)	0.24058 (7)	0.0241 (2)
C67	0.83886 (19)	0.31352 (10)	0.29263 (10)	0.0250 (3)
C61	0.99304 (18)	0.39019 (10)	0.33463 (9)	0.0208 (3)
C62	1.0505 (2)	0.44570 (10)	0.27876 (10)	0.0236 (3)
C63	1.1890 (2)	0.51865 (11)	0.31678 (11)	0.0280 (3)
C64	1.2730 (2)	0.53553 (11)	0.41100 (11)	0.0304 (4)
C65	1.2174 (2)	0.48152 (12)	0.46718 (10)	0.0304 (4)
C66	1.0771 (2)	0.40920 (11)	0.42901 (10)	0.0261 (3)
H2B	0.2225	0.0435	0.1936	0.030*
H2A	0.4446	0.0513	0.2502	0.030*
H41A	−0.2198	0.2441	0.0773	0.030*
H41B	−0.2298	0.2416	−0.0241	0.030*
H42A	−0.3966	0.3919	−0.0593	0.030*
H42B	−0.3855	0.3951	0.0421	0.030*
H43A	−0.5987	0.2506	−0.0934	0.031*
H43B	−0.5923	0.2580	0.0070	0.031*
H44A	−0.7526	0.4118	−0.0359	0.046*
H44B	−0.8855	0.3260	−0.1006	0.046*
H44C	−0.7704	0.3972	−0.1379	0.046*
H4	−0.0428	0.4015	0.0444	0.025*
H67A	0.8687	0.2713	0.2509	0.030*
H67B	0.8322	0.2727	0.3417	0.030*
H62	0.9942	0.4334	0.2140	0.028*
H63	1.2260	0.5569	0.2781	0.034*
H64	1.3698	0.5847	0.4373	0.036*
H65	1.2751	0.4938	0.5320	0.036*
H66	1.0383	0.3724	0.4679	0.031*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0155 (5)	0.0174 (6)	0.0242 (6)	−0.0004 (5)	0.0057 (5)	0.0009 (4)
C2	0.0184 (7)	0.0172 (6)	0.0207 (6)	−0.0001 (5)	0.0082 (5)	−0.0005 (5)
N2	0.0164 (6)	0.0165 (6)	0.0347 (7)	−0.0010 (5)	0.0058 (5)	0.0030 (5)
N3	0.0156 (5)	0.0172 (6)	0.0242 (6)	0.0000 (5)	0.0067 (4)	0.0010 (4)
C4	0.0151 (6)	0.0193 (7)	0.0187 (6)	−0.0005 (5)	0.0068 (5)	−0.0001 (5)
C41	0.0143 (7)	0.0226 (7)	0.0326 (8)	−0.0031 (6)	0.0058 (6)	−0.0032 (6)
C42	0.0154 (7)	0.0233 (7)	0.0323 (8)	−0.0013 (6)	0.0076 (6)	0.0044 (6)
C43	0.0171 (7)	0.0245 (7)	0.0322 (8)	−0.0026 (6)	0.0082 (6)	−0.0042 (6)
C44	0.0165 (7)	0.0368 (9)	0.0334 (8)	−0.0013 (7)	0.0070 (6)	−0.0002 (7)
N4	0.0138 (6)	0.0186 (6)	0.0261 (6)	−0.0008 (5)	0.0048 (5)	0.0034 (5)
C5	0.0145 (6)	0.0171 (6)	0.0197 (6)	−0.0010 (5)	0.0061 (5)	0.0019 (5)
N5	0.0156 (5)	0.0199 (6)	0.0249 (6)	0.0027 (5)	0.0069 (5)	0.0047 (5)
O5	0.0169 (5)	0.0215 (5)	0.0310 (5)	0.0033 (4)	0.0062 (4)	0.0068 (4)
C6	0.0150 (6)	0.0186 (6)	0.0198 (6)	−0.0012 (5)	0.0062 (5)	0.0001 (5)
O6	0.0107 (5)	0.0185 (5)	0.0344 (6)	−0.0001 (4)	0.0024 (4)	0.0040 (4)
C67	0.0126 (6)	0.0219 (7)	0.0329 (8)	0.0035 (6)	0.0034 (6)	0.0028 (6)
C61	0.0117 (6)	0.0194 (6)	0.0275 (7)	0.0037 (5)	0.0054 (5)	0.0002 (5)
C62	0.0193 (7)	0.0252 (7)	0.0259 (7)	0.0021 (6)	0.0097 (6)	−0.0011 (6)
C63	0.0208 (7)	0.0245 (7)	0.0423 (9)	0.0017 (6)	0.0172 (6)	0.0015 (6)
C64	0.0145 (7)	0.0244 (7)	0.0475 (9)	−0.0001 (6)	0.0098 (6)	−0.0076 (7)
C65	0.0192 (7)	0.0349 (9)	0.0285 (8)	0.0046 (6)	0.0030 (6)	−0.0068 (6)
C66	0.0182 (7)	0.0306 (8)	0.0281 (7)	0.0052 (6)	0.0090 (6)	0.0041 (6)

Geometric parameters (Å, º)

N1—C6	1.3080 (17)	C44—H44C	0.9800
N1—C2	1.3709 (17)	N4—H4	0.8800
C2—N2	1.3301 (17)	C5—N5	1.3488 (17)
C2—N3	1.3363 (17)	C5—C6	1.4266 (18)
N2—H2A	0.8800	N5—O5	1.2724 (14)
N2—H2B	0.8800	C6—O6	1.3349 (16)
N3—C4	1.3406 (17)	O6—C67	1.4602 (15)
C4—N4	1.3255 (16)	C67—C61	1.4964 (19)
C4—C5	1.4451 (18)	C67—H67A	0.9900
C41—N4	1.4611 (17)	C67—H67B	0.9900
C41—C42	1.5056 (19)	C61—C66	1.3858 (19)
C41—H41A	0.9900	C61—C62	1.393 (2)
C41—H41B	0.9900	C62—C63	1.385 (2)
C42—C43	1.5183 (18)	C62—H62	0.9500
C42—H42A	0.9900	C63—C64	1.378 (2)
C42—H42B	0.9900	C63—H63	0.9500
C43—C44	1.512 (2)	C64—C65	1.377 (2)
C43—H43A	0.9900	C64—H64	0.9500
C43—H43B	0.9900	C65—C66	1.386 (2)
C44—H44A	0.9800	C65—H65	0.9500
C44—H44B	0.9800	C66—H66	0.9500
C6—N1—C2	114.79 (11)	C4—N4—C41	123.16 (11)
N2—C2—N3	116.83 (12)	C4—N4—H4	118.4
N2—C2—N1	115.30 (12)	C41—N4—H4	118.4
N3—C2—N1	127.87 (12)	N5—C5—C6	117.68 (11)
C2—N2—H2A	120.0	N5—C5—C4	127.44 (12)
C2—N2—H2B	120.0	C6—C5—C4	114.81 (12)
H2A—N2—H2B	120.0	O5—N5—C5	117.53 (11)
C2—N3—C4	116.66 (11)	N1—C6—O6	119.43 (12)
N4—C4—N3	118.06 (12)	N1—C6—C5	124.40 (12)
N4—C4—C5	120.71 (12)	O6—C6—C5	116.17 (11)
N3—C4—C5	121.20 (11)	C6—O6—C67	117.35 (10)
N4—C41—C42	111.41 (11)	O6—C67—C61	106.38 (10)
N4—C41—H41A	109.3	O6—C67—H67A	110.5
C42—C41—H41A	109.3	C61—C67—H67A	110.5
N4—C41—H41B	109.3	O6—C67—H67B	110.5
C42—C41—H41B	109.3	C61—C67—H67B	110.5
H41A—C41—H41B	108.0	H67A—C67—H67B	108.6
C41—C42—C43	112.93 (12)	C66—C61—C62	118.81 (13)
C41—C42—H42A	109.0	C66—C61—C67	120.86 (13)
C43—C42—H42A	109.0	C62—C61—C67	120.31 (12)
C41—C42—H42B	109.0	C63—C62—C61	120.62 (13)
C43—C42—H42B	109.0	C63—C62—H62	119.7
H42A—C42—H42B	107.8	C61—C62—H62	119.7
C44—C43—C42	112.20 (12)	C64—C63—C62	119.70 (14)
C44—C43—H43A	109.2	C64—C63—H63	120.2
C42—C43—H43A	109.2	C62—C63—H63	120.2
C44—C43—H43B	109.2	C65—C64—C63	120.41 (14)
C42—C43—H43B	109.2	C65—C64—H64	119.8
H43A—C43—H43B	107.9	C63—C64—H64	119.8
C43—C44—H44A	109.5	C64—C65—C66	119.91 (14)
C43—C44—H44B	109.5	C64—C65—H65	120.0
H44A—C44—H44B	109.5	C66—C65—H65	120.0
C43—C44—H44C	109.5	C65—C66—C61	120.53 (14)
H44A—C44—H44C	109.5	C65—C66—H66	119.7
H44B—C44—H44C	109.5	C61—C66—H66	119.7
C6—N1—C2—N2	−176.29 (12)	C2—N1—C6—C5	−1.59 (19)
C6—N1—C2—N3	4.8 (2)	N5—C5—C6—N1	174.27 (13)
N2—C2—N3—C4	178.40 (12)	C4—C5—C6—N1	−2.86 (19)
N1—C2—N3—C4	−2.7 (2)	N5—C5—C6—O6	−6.15 (17)
C2—N3—C4—N4	179.13 (11)	C4—C5—C6—O6	176.73 (11)
C2—N3—C4—C5	−2.54 (18)	N1—C6—O6—C67	2.13 (18)
N4—C41—C42—C43	−179.55 (12)	C5—C6—O6—C67	−177.48 (11)
C41—C42—C43—C44	−177.66 (12)	C6—O6—C67—C61	−170.15 (11)
N3—C4—N4—C41	3.62 (19)	O6—C67—C61—C66	107.49 (14)
C5—C4—N4—C41	−174.71 (12)	O6—C67—C61—C62	−70.68 (15)
C42—C41—N4—C4	162.50 (12)	C66—C61—C62—C63	−0.1 (2)
N4—C4—C5—N5	6.5 (2)	C67—C61—C62—C63	178.13 (12)
N3—C4—C5—N5	−171.76 (13)	C61—C62—C63—C64	1.0 (2)
N4—C4—C5—C6	−176.69 (12)	C62—C63—C64—C65	−1.2 (2)
N3—C4—C5—C6	5.03 (18)	C63—C64—C65—C66	0.5 (2)
C6—C5—N5—O5	178.33 (11)	C64—C65—C66—C61	0.5 (2)
C4—C5—N5—O5	−5.0 (2)	C62—C61—C66—C65	−0.7 (2)
C2—N1—C6—O6	178.83 (11)	C67—C61—C66—C65	−178.85 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O5	0.88	2.00	2.642 (2)	129
N2—H2A···N5^i	0.88	2.20	3.058 (2)	164
N2—H2B···Cg1^i	0.88	2.67	3.537 (2)	171

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

(3) 2-Amino-6-benzyloxy-4-(N-dodecylamino)-5-nitrosopyrimidine

Crystal data

C23H35N5O2	Z = 2
Mr = 413.56	F(000) = 448
Triclinic, P1	Dx = 1.204 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3567 (4) Å	Cell parameters from 4147 reflections
b = 7.7784 (4) Å	θ = 3.0–27.5°
c = 21.4725 (14) Å	µ = 0.08 mm^−1
α = 92.000 (2)°	T = 120 K
β = 99.840 (2)°	Plate, purple
γ = 108.760 (2)°	0.18 × 0.18 × 0.08 mm
V = 1141.00 (11) Å^3

Data collection

Kappa-CCD diffractometer	4147 independent reflections
Radiation source: fine-focus sealed X-ray tube	2819 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
ϕ scans, and ω scans with κ offsets	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −9→9
Tmin = 0.976, Tmax = 0.994	k = −9→10
10984 measured reflections	l = −27→27

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.140	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0752P)^2 + 0.1136P] where P = (Fo^2 + 2Fc^2)/3
4147 reflections	(Δ/σ)max < 0.001
272 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

Experimental. bsorpt_correction_T_max 0.9947

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

	x	y	z	Uiso*/Ueq
N1	0.5363 (2)	0.19353 (19)	0.55144 (6)	0.0231 (4)
C2	0.3905 (3)	0.2288 (2)	0.51088 (8)	0.0234 (4)
N2	0.2243 (2)	0.1990 (2)	0.53114 (7)	0.0293 (4)
N3	0.3984 (2)	0.29059 (19)	0.45348 (7)	0.0236 (4)
C4	0.5688 (3)	0.3270 (2)	0.43450 (8)	0.0223 (4)
C41	0.4311 (3)	0.4504 (3)	0.34147 (8)	0.0278 (4)
C42	0.3255 (3)	0.3251 (3)	0.28115 (8)	0.0273 (4)
C43	0.1503 (3)	0.3784 (3)	0.25104 (8)	0.0288 (5)
C44	0.0217 (3)	0.2609 (3)	0.19140 (9)	0.0307 (5)
C45	−0.1591 (3)	0.3147 (3)	0.17023 (8)	0.0284 (4)
C46	−0.2922 (3)	0.2164 (3)	0.10839 (9)	0.0311 (5)
C47	−0.4619 (3)	0.2879 (3)	0.08934 (8)	0.0294 (5)
C48	−0.5937 (3)	0.2057 (3)	0.02553 (9)	0.0311 (5)
C49	−0.7587 (3)	0.2848 (3)	0.00868 (8)	0.0306 (5)
C410	−0.8951 (3)	0.2067 (3)	−0.05445 (9)	0.0320 (5)
C411	−1.0583 (3)	0.2880 (3)	−0.06900 (9)	0.0359 (5)
C412	−1.1994 (3)	0.2083 (3)	−0.13125 (10)	0.0469 (6)
N4	0.5860 (2)	0.3970 (2)	0.37904 (7)	0.0258 (4)
C5	0.7347 (3)	0.2925 (2)	0.47208 (8)	0.0205 (4)
O5	0.94503 (18)	0.39005 (16)	0.40582 (6)	0.0277 (3)
N5	0.9124 (2)	0.32132 (19)	0.45776 (7)	0.0232 (4)
C6	0.7010 (3)	0.2256 (2)	0.53197 (8)	0.0214 (4)
C61	1.0065 (3)	0.1385 (2)	0.67025 (8)	0.0228 (4)
C62	1.1182 (3)	0.2673 (2)	0.72010 (8)	0.0287 (4)
C63	1.2871 (3)	0.2512 (3)	0.75526 (9)	0.0337 (5)
C64	1.3490 (3)	0.1083 (3)	0.73945 (9)	0.0328 (5)
C65	1.2403 (3)	−0.0204 (3)	0.68956 (9)	0.0301 (5)
C66	1.0671 (3)	−0.0071 (2)	0.65580 (8)	0.0273 (4)
C67	0.8200 (3)	0.1525 (3)	0.63341 (8)	0.0264 (4)
O6	0.85125 (16)	0.19713 (15)	0.56988 (5)	0.0236 (3)
H2A	0.1251	0.2197	0.5073	0.035*
H2B	0.2127	0.1585	0.5685	0.035*
H41A	0.4887	0.5758	0.3299	0.033*
H41B	0.3342	0.4526	0.3681	0.033*
H42A	0.2807	0.1968	0.2913	0.033*
H42B	0.4158	0.3360	0.2510	0.033*
H43A	0.0676	0.3752	0.2831	0.035*
H43B	0.1992	0.5061	0.2405	0.035*
H44A	0.0976	0.2751	0.1569	0.037*
H44B	−0.0189	0.1311	0.1999	0.037*
H45A	−0.2369	0.2930	0.2043	0.034*
H45B	−0.1160	0.4474	0.1659	0.034*
H46A	−0.3447	0.0844	0.1131	0.037*
H46B	−0.2149	0.2320	0.0742	0.037*
H47A	−0.5428	0.2645	0.1225	0.035*
H47B	−0.4080	0.4217	0.0884	0.035*
H48A	−0.6510	0.0721	0.0264	0.037*
H48B	−0.5138	0.2276	−0.0080	0.037*
H49A	−0.8368	0.2636	0.0426	0.037*
H49B	−0.7003	0.4183	0.0080	0.037*
H41C	−0.9538	0.0731	−0.0541	0.038*
H41D	−0.8182	0.2292	−0.0887	0.038*
H41E	−1.1326	0.2684	−0.0341	0.043*
H41F	−0.9993	0.4213	−0.0702	0.043*
H41G	−1.1273	0.2271	−0.1662	0.070*
H41H	−1.2981	0.2690	−0.1380	0.070*
H41I	−1.2639	0.0774	−0.1297	0.070*
H4	0.6945	0.4114	0.3646	0.031*
H62	1.0784	0.3678	0.7303	0.034*
H63	1.3604	0.3383	0.7902	0.040*
H64	1.4664	0.0985	0.7630	0.039*
H65	1.2837	−0.1178	0.6783	0.036*
H66	0.9897	−0.0984	0.6226	0.033*
H67A	0.7123	0.0352	0.6309	0.032*
H67B	0.7843	0.2487	0.6546	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0173 (9)	0.0279 (9)	0.0249 (8)	0.0107 (7)	0.0008 (7)	−0.0006 (6)
C2	0.0181 (11)	0.0246 (10)	0.0269 (10)	0.0088 (8)	0.0004 (8)	−0.0033 (7)
N2	0.0183 (9)	0.0450 (10)	0.0273 (9)	0.0140 (7)	0.0044 (7)	0.0051 (7)
N3	0.0173 (9)	0.0305 (9)	0.0242 (8)	0.0106 (7)	0.0020 (7)	0.0011 (6)
C4	0.0190 (10)	0.0222 (10)	0.0246 (9)	0.0085 (8)	−0.0009 (8)	−0.0030 (7)
C41	0.0266 (11)	0.0344 (11)	0.0255 (10)	0.0159 (9)	0.0015 (9)	0.0057 (8)
C42	0.0259 (11)	0.0303 (11)	0.0278 (10)	0.0130 (8)	0.0038 (9)	0.0028 (8)
C43	0.0270 (11)	0.0322 (11)	0.0280 (10)	0.0119 (9)	0.0033 (9)	0.0045 (8)
C44	0.0271 (12)	0.0385 (12)	0.0265 (10)	0.0118 (9)	0.0035 (9)	0.0010 (8)
C45	0.0272 (12)	0.0306 (11)	0.0260 (10)	0.0097 (9)	0.0008 (9)	0.0022 (8)
C46	0.0279 (12)	0.0351 (11)	0.0273 (10)	0.0084 (9)	0.0018 (9)	0.0020 (8)
C47	0.0274 (12)	0.0300 (11)	0.0278 (10)	0.0089 (9)	−0.0010 (9)	0.0008 (8)
C48	0.0282 (12)	0.0327 (11)	0.0290 (10)	0.0085 (9)	0.0001 (9)	0.0010 (8)
C49	0.0280 (12)	0.0326 (11)	0.0288 (10)	0.0081 (9)	0.0023 (9)	0.0031 (8)
C410	0.0293 (12)	0.0332 (11)	0.0292 (10)	0.0071 (9)	0.0006 (9)	0.0038 (8)
C411	0.0300 (12)	0.0426 (12)	0.0306 (11)	0.0084 (9)	0.0001 (9)	0.0074 (9)
C412	0.0385 (14)	0.0486 (14)	0.0422 (13)	0.0067 (11)	−0.0088 (11)	0.0106 (10)
N4	0.0208 (9)	0.0363 (9)	0.0240 (8)	0.0144 (7)	0.0041 (7)	0.0035 (6)
C5	0.0162 (10)	0.0219 (10)	0.0232 (9)	0.0076 (8)	0.0014 (8)	−0.0026 (7)
O5	0.0262 (8)	0.0324 (7)	0.0264 (7)	0.0108 (6)	0.0079 (6)	0.0036 (5)
N5	0.0210 (9)	0.0252 (9)	0.0232 (8)	0.0077 (7)	0.0042 (7)	−0.0004 (6)
C6	0.0173 (11)	0.0210 (10)	0.0259 (9)	0.0091 (8)	0.0000 (8)	−0.0032 (7)
C61	0.0203 (10)	0.0293 (10)	0.0206 (9)	0.0097 (8)	0.0050 (8)	0.0049 (7)
C62	0.0295 (12)	0.0296 (11)	0.0285 (10)	0.0135 (9)	0.0036 (9)	0.0004 (8)
C63	0.0307 (12)	0.0346 (12)	0.0285 (10)	0.0068 (9)	−0.0052 (9)	−0.0025 (8)
C64	0.0240 (11)	0.0398 (12)	0.0331 (11)	0.0125 (9)	−0.0029 (9)	0.0089 (9)
C65	0.0297 (12)	0.0324 (11)	0.0334 (11)	0.0181 (9)	0.0048 (9)	0.0044 (8)
C66	0.0249 (11)	0.0305 (11)	0.0252 (10)	0.0101 (8)	0.0006 (8)	−0.0004 (7)
C67	0.0251 (11)	0.0347 (11)	0.0218 (9)	0.0140 (9)	0.0030 (8)	0.0025 (7)
O6	0.0179 (7)	0.0312 (7)	0.0235 (6)	0.0122 (6)	0.0008 (5)	0.0032 (5)

Geometric parameters (Å, º)

N1—C6	1.300 (2)	C48—H48B	0.99
N1—C2	1.368 (2)	C49—C410	1.516 (2)
C2—N2	1.321 (2)	C49—H49A	0.99
C2—N3	1.342 (2)	C49—H49B	0.99
N2—H2A	0.88	C410—C411	1.520 (3)
N2—H2B	0.88	C410—H41C	0.99
N3—C4	1.331 (2)	C410—H41D	0.99
C4—N4	1.335 (2)	C411—C412	1.517 (3)
C4—C5	1.450 (2)	C411—H41E	0.99
C41—N4	1.462 (2)	C411—H41F	0.99
C41—C42	1.521 (2)	C412—H41G	0.98
C41—H41A	0.99	C412—H41H	0.98
C41—H41B	0.99	C412—H41I	0.98
C42—C43	1.527 (2)	N4—H4	0.88
C42—H42A	0.99	C5—N5	1.344 (2)
C42—H42B	0.99	C5—C6	1.435 (2)
C43—C44	1.522 (2)	O5—N5	1.2799 (17)
C43—H43A	0.99	C6—O6	1.3400 (19)
C43—H43B	0.99	C61—C62	1.385 (2)
C44—C45	1.522 (2)	C61—C66	1.388 (2)
C44—H44A	0.99	C61—C67	1.500 (2)
C44—H44B	0.99	C62—C63	1.384 (3)
C45—C46	1.520 (2)	C62—H62	0.95
C45—H45A	0.99	C63—C64	1.382 (3)
C45—H45B	0.99	C63—H63	0.95
C46—C47	1.524 (3)	C64—C65	1.381 (3)
C46—H46A	0.99	C64—H64	0.95
C46—H46B	0.99	C65—C66	1.391 (2)
C47—C48	1.521 (2)	C65—H65	0.95
C47—H47A	0.99	C66—H66	0.95
C47—H47B	0.99	C67—O6	1.457 (2)
C48—C49	1.526 (3)	C67—H67A	0.99
C48—H48A	0.99	C67—H67B	0.99
C6—N1—C2	115.76 (15)	C410—C49—C48	114.93 (15)
N2—C2—N3	116.97 (15)	C410—C49—H49A	108.5
N2—C2—N1	115.71 (16)	C48—C49—H49A	108.5
N3—C2—N1	127.31 (17)	C410—C49—H49B	108.5
C2—N2—H2A	120.0	C48—C49—H49B	108.5
C2—N2—H2B	120.0	H49A—C49—H49B	107.5
H2A—N2—H2B	120.0	C49—C410—C411	113.15 (16)
C4—N3—C2	116.57 (14)	C49—C410—H41C	108.9
N3—C4—N4	118.61 (15)	C411—C410—H41C	108.9
N3—C4—C5	121.99 (16)	C49—C410—H41D	108.9
N4—C4—C5	119.41 (16)	C411—C410—H41D	108.9
N4—C41—C42	113.97 (15)	H41C—C410—H41D	107.8
N4—C41—H41A	108.8	C412—C411—C410	113.96 (17)
C42—C41—H41A	108.8	C412—C411—H41E	108.8
N4—C41—H41B	108.8	C410—C411—H41E	108.8
C42—C41—H41B	108.8	C412—C411—H41F	108.8
H41A—C41—H41B	107.7	C410—C411—H41F	108.8
C41—C42—C43	109.07 (14)	H41E—C411—H41F	107.7
C41—C42—H42A	109.9	C411—C412—H41G	109.5
C43—C42—H42A	109.9	C411—C412—H41H	109.5
C41—C42—H42B	109.9	H41G—C412—H41H	109.5
C43—C42—H42B	109.9	C411—C412—H41I	109.5
H42A—C42—H42B	108.3	H41G—C412—H41I	109.5
C44—C43—C42	116.20 (15)	H41H—C412—H41I	109.5
C44—C43—H43A	108.2	C4—N4—C41	122.29 (15)
C42—C43—H43A	108.2	C4—N4—H4	118.9
C44—C43—H43B	108.2	C41—N4—H4	118.9
C42—C43—H43B	108.2	N5—C5—C6	118.33 (15)
H43A—C43—H43B	107.4	N5—C5—C4	127.50 (16)
C45—C44—C43	111.09 (15)	C6—C5—C4	114.14 (16)
C45—C44—H44A	109.4	O5—N5—C5	118.12 (13)
C43—C44—H44A	109.4	N1—C6—O6	118.88 (15)
C45—C44—H44B	109.4	N1—C6—C5	124.15 (15)
C43—C44—H44B	109.4	O6—C6—C5	116.96 (15)
H44A—C44—H44B	108.0	C62—C61—C66	118.90 (16)
C46—C45—C44	116.17 (15)	C62—C61—C67	120.89 (16)
C46—C45—H45A	108.2	C66—C61—C67	120.19 (16)
C44—C45—H45A	108.2	C63—C62—C61	120.82 (17)
C46—C45—H45B	108.2	C63—C62—H62	119.6
C44—C45—H45B	108.2	C61—C62—H62	119.6
H45A—C45—H45B	107.4	C64—C63—C62	119.83 (17)
C45—C46—C47	112.09 (15)	C64—C63—H63	120.1
C45—C46—H46A	109.2	C62—C63—H63	120.1
C47—C46—H46A	109.2	C65—C64—C63	120.09 (17)
C45—C46—H46B	109.2	C65—C64—H64	120.0
C47—C46—H46B	109.2	C63—C64—H64	120.0
H46A—C46—H46B	107.9	C64—C65—C66	119.80 (17)
C48—C47—C46	115.25 (15)	C64—C65—H65	120.1
C48—C47—H47A	108.5	C66—C65—H65	120.1
C46—C47—H47A	108.5	C61—C66—C65	120.49 (17)
C48—C47—H47B	108.5	C61—C66—H66	119.8
C46—C47—H47B	108.5	C65—C66—H66	119.8
H47A—C47—H47B	107.5	O6—C67—C61	107.91 (14)
C47—C48—C49	112.77 (15)	O6—C67—H67A	110.1
C47—C48—H48A	109.0	C61—C67—H67A	110.1
C49—C48—H48A	109.0	O6—C67—H67B	110.1
C47—C48—H48B	109.0	C61—C67—H67B	110.1
C49—C48—H48B	109.0	H67A—C67—H67B	108.4
H48A—C48—H48B	107.8	C6—O6—C67	115.32 (13)
C6—N1—C2—N2	−178.94 (14)	N4—C4—C5—C6	177.16 (15)
C6—N1—C2—N3	0.7 (3)	C6—C5—N5—O5	−176.38 (14)
N2—C2—N3—C4	177.46 (14)	C4—C5—N5—O5	1.4 (2)
N1—C2—N3—C4	−2.2 (3)	C2—N1—C6—O6	178.79 (14)
C2—N3—C4—N4	−176.84 (15)	C2—N1—C6—C5	−0.4 (2)
C2—N3—C4—C5	3.3 (2)	N5—C5—C6—N1	179.52 (14)
N4—C41—C42—C43	172.21 (15)	C4—C5—C6—N1	1.5 (2)
C41—C42—C43—C44	−177.34 (16)	N5—C5—C6—O6	0.3 (2)
C42—C43—C44—C45	173.80 (16)	C4—C5—C6—O6	−177.72 (14)
C43—C44—C45—C46	175.76 (16)	C66—C61—C62—C63	−0.3 (3)
C44—C45—C46—C47	−176.54 (16)	C67—C61—C62—C63	178.03 (17)
C45—C46—C47—C48	175.84 (16)	C61—C62—C63—C64	2.0 (3)
C46—C47—C48—C49	−179.09 (16)	C62—C63—C64—C65	−1.4 (3)
C47—C48—C49—C410	−179.74 (16)	C63—C64—C65—C66	−0.9 (3)
C48—C49—C410—C411	179.44 (17)	C62—C61—C66—C65	−2.0 (3)
C49—C410—C411—C412	−178.59 (17)	C67—C61—C66—C65	179.71 (17)
N3—C4—N4—C41	5.8 (2)	C64—C65—C66—C61	2.5 (3)
C5—C4—N4—C41	−174.38 (15)	C62—C61—C67—O6	110.83 (18)
C42—C41—N4—C4	−108.68 (19)	C66—C61—C67—O6	−70.9 (2)
N3—C4—C5—N5	179.17 (15)	N1—C6—O6—C67	−7.0 (2)
N4—C4—C5—N5	−0.7 (3)	C5—C6—O6—C67	172.25 (14)
N3—C4—C5—C6	−3.0 (2)	C61—C67—O6—C6	−176.06 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O5	0.88	1.96	2.624 (2)	131
N2—H2A···N5^i	0.88	2.12	2.987 (2)	169

Symmetry code: (i) x−1, y, z.

(4) 2-amino-6-benzyloxy-4-(N-cyclohexylamino)-5-nitrosopyrimidine

Crystal data

C17H21N5O2	Z = 2
Mr = 327.39	F(000) = 348
Triclinic, P1	Dx = 1.365 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2656 (5) Å	Cell parameters from 3442 reflections
b = 10.6077 (6) Å	θ = 3.2–27.5°
c = 10.6743 (7) Å	µ = 0.09 mm^−1
α = 64.841 (4)°	T = 120 K
β = 71.021 (3)°	Block, red
γ = 87.275 (5)°	0.12 × 0.08 × 0.06 mm
V = 796.56 (9) Å^3

Data collection

Kappa-CCD diffractometer	3442 independent reflections
Radiation source: fine-focus sealed X-ray tube	1528 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.128
ϕ scans, and ω scans with κ offsets	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −10→10
Tmin = 0.974, Tmax = 0.994	k = −13→13
11753 measured reflections	l = −13→13

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.146	H-atom parameters constrained
S = 0.95	w = 1/[σ^2(Fo^2) + (0.0553P)^2] where P = (Fo^2 + 2Fc^2)/3
3442 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 0.39 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	0.7984 (3)	0.1635 (3)	0.5108 (3)	0.0179 (6)
O5	0.4348 (2)	0.1762 (2)	0.2518 (2)	0.0205 (5)
C2	0.9370 (4)	0.1769 (3)	0.3892 (3)	0.0173 (7)
N2	1.0879 (3)	0.1751 (3)	0.4071 (3)	0.0228 (7)
N3	0.9343 (3)	0.1926 (3)	0.2587 (3)	0.0188 (6)
C4	0.7790 (4)	0.1916 (3)	0.2447 (3)	0.0166 (7)
C41	0.9095 (4)	0.2424 (3)	−0.0196 (3)	0.0198 (7)
C42	0.9246 (4)	0.3956 (4)	−0.1256 (4)	0.0270 (8)
C43	1.0627 (4)	0.4292 (4)	−0.2743 (3)	0.0273 (8)
C44	1.0341 (4)	0.3353 (4)	−0.3406 (3)	0.0264 (8)
C45	1.0200 (4)	0.1814 (4)	−0.2339 (3)	0.0255 (8)
C46	0.8800 (4)	0.1481 (3)	−0.0860 (3)	0.0221 (8)
N4	0.7667 (3)	0.2110 (3)	0.1173 (3)	0.0205 (6)
N5	0.4587 (3)	0.1629 (3)	0.3711 (3)	0.0187 (6)
O6	0.5049 (2)	0.1449 (2)	0.6097 (2)	0.0196 (5)
C5	0.6217 (4)	0.1701 (3)	0.3669 (3)	0.0152 (7)
C6	0.6473 (4)	0.1587 (3)	0.4980 (3)	0.0162 (7)
C61	0.4934 (4)	0.2485 (3)	0.7763 (3)	0.0164 (7)
C62	0.5612 (4)	0.3820 (3)	0.6663 (3)	0.0199 (8)
C63	0.5404 (4)	0.4969 (4)	0.6961 (3)	0.0238 (8)
C64	0.4498 (4)	0.4807 (4)	0.8378 (3)	0.0243 (8)
C65	0.3813 (4)	0.3493 (3)	0.9481 (3)	0.0223 (8)
C66	0.4022 (4)	0.2338 (3)	0.9179 (3)	0.0217 (8)
C67	0.5218 (4)	0.1209 (3)	0.7491 (3)	0.0177 (7)
H2A	1.1828	0.1842	0.3345	0.027*
H2B	1.0936	0.1650	0.4918	0.027*
H41	1.0187	0.2225	0.0032	0.024*
H42A	0.9532	0.4544	−0.0828	0.032*
H42B	0.8125	0.4187	−0.1398	0.032*
H43A	1.0626	0.5280	−0.3424	0.033*
H43B	1.1769	0.4182	−0.2619	0.033*
H44A	1.1311	0.3553	−0.4327	0.032*
H44B	0.9272	0.3550	−0.3652	0.032*
H45A	1.1318	0.1591	−0.2187	0.031*
H45B	0.9932	0.1220	−0.2769	0.031*
H46A	0.7664	0.1602	−0.0996	0.027*
H46B	0.8786	0.0491	−0.0175	0.027*
H4	0.6623	0.2044	0.1147	0.025*
H62	0.6227	0.3940	0.5690	0.024*
H63	0.5880	0.5874	0.6198	0.029*
H64	0.4352	0.5600	0.8585	0.029*
H65	0.3197	0.3379	1.0451	0.027*
H66	0.3540	0.1435	0.9944	0.026*
H67A	0.6383	0.0942	0.7488	0.021*
H67B	0.4370	0.0423	0.8297	0.021*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0136 (13)	0.0226 (16)	0.0179 (14)	0.0026 (11)	−0.0041 (12)	−0.0102 (13)
O5	0.0192 (11)	0.0275 (14)	0.0182 (12)	0.0023 (9)	−0.0073 (10)	−0.0122 (11)
C2	0.0184 (17)	0.0157 (19)	0.0175 (17)	0.0030 (13)	−0.0048 (15)	−0.0079 (15)
N2	0.0134 (13)	0.0380 (19)	0.0189 (15)	0.0016 (12)	−0.0057 (12)	−0.0138 (14)
N3	0.0149 (13)	0.0258 (17)	0.0184 (14)	0.0027 (11)	−0.0084 (12)	−0.0100 (13)
C4	0.0186 (16)	0.0141 (18)	0.0172 (17)	−0.0008 (13)	−0.0049 (15)	−0.0074 (15)
C41	0.0134 (15)	0.028 (2)	0.0157 (17)	0.0023 (14)	−0.0030 (14)	−0.0089 (16)
C42	0.0264 (18)	0.028 (2)	0.0260 (19)	0.0012 (15)	−0.0028 (16)	−0.0149 (18)
C43	0.0256 (18)	0.028 (2)	0.0198 (18)	−0.0025 (15)	−0.0028 (16)	−0.0059 (17)
C44	0.0217 (17)	0.037 (2)	0.0170 (18)	0.0003 (15)	−0.0052 (15)	−0.0091 (17)
C45	0.0241 (18)	0.031 (2)	0.0220 (19)	−0.0011 (15)	−0.0042 (16)	−0.0145 (17)
C46	0.0199 (17)	0.026 (2)	0.0168 (18)	0.0036 (15)	−0.0041 (15)	−0.0072 (16)
N4	0.0129 (13)	0.0361 (18)	0.0155 (15)	0.0020 (12)	−0.0047 (12)	−0.0138 (13)
N5	0.0202 (14)	0.0192 (16)	0.0229 (15)	0.0052 (11)	−0.0100 (12)	−0.0128 (13)
O6	0.0157 (11)	0.0285 (14)	0.0158 (12)	0.0021 (9)	−0.0044 (10)	−0.0112 (11)
C5	0.0128 (15)	0.0174 (18)	0.0166 (17)	0.0003 (13)	−0.0046 (13)	−0.0086 (14)
C6	0.0170 (17)	0.0134 (19)	0.0146 (17)	0.0029 (13)	−0.0021 (15)	−0.0053 (15)
C61	0.0135 (15)	0.0215 (19)	0.0156 (17)	0.0046 (13)	−0.0056 (14)	−0.0089 (15)
C62	0.0168 (16)	0.024 (2)	0.0134 (17)	−0.0001 (14)	−0.0012 (14)	−0.0058 (16)
C63	0.0223 (17)	0.019 (2)	0.024 (2)	0.0008 (14)	−0.0053 (16)	−0.0060 (16)
C64	0.0288 (18)	0.022 (2)	0.025 (2)	0.0026 (15)	−0.0109 (16)	−0.0121 (18)
C65	0.0262 (18)	0.029 (2)	0.0163 (18)	0.0070 (16)	−0.0091 (15)	−0.0132 (17)
C66	0.0237 (17)	0.023 (2)	0.0162 (18)	0.0020 (15)	−0.0059 (15)	−0.0071 (16)
C67	0.0194 (16)	0.0196 (19)	0.0105 (16)	−0.0004 (14)	−0.0033 (14)	−0.0044 (15)

Geometric parameters (Å, º)

N1—C6	1.305 (4)	C45—H45A	0.99
N1—C2	1.382 (4)	C45—H45B	0.99
O5—N5	1.301 (3)	C46—H46A	0.99
C2—N2	1.320 (4)	C46—H46B	0.99
C2—N3	1.338 (4)	N4—H4	0.88
N2—H2A	0.88	N5—C5	1.338 (4)
N2—H2B	0.88	O6—C6	1.336 (3)
N3—C4	1.341 (4)	O6—C67	1.452 (3)
C4—N4	1.323 (4)	C5—C6	1.436 (4)
C4—C5	1.454 (4)	C61—C62	1.390 (4)
C41—N4	1.463 (4)	C61—C66	1.395 (4)
C41—C42	1.517 (4)	C61—C67	1.494 (4)
C41—C46	1.517 (4)	C62—C63	1.375 (4)
C41—H41	1.00	C62—H62	0.95
C42—C43	1.526 (4)	C63—C64	1.390 (4)
C42—H42A	0.99	C63—H63	0.95
C42—H42B	0.99	C64—C65	1.377 (4)
C43—C44	1.510 (4)	C64—H64	0.95
C43—H43A	0.99	C65—C66	1.383 (4)
C43—H43B	0.99	C65—H65	0.95
C44—C45	1.526 (5)	C66—H66	0.95
C44—H44A	0.99	C67—H67A	0.99
C44—H44B	0.99	C67—H67B	0.99
C45—C46	1.528 (4)
C6—N1—C2	115.5 (2)	C41—C46—C45	111.5 (2)
N2—C2—N3	118.0 (3)	C41—C46—H46A	109.3
N2—C2—N1	114.3 (2)	C45—C46—H46A	109.3
N3—C2—N1	127.6 (3)	C41—C46—H46B	109.3
C2—N2—H2A	120.0	C45—C46—H46B	109.3
C2—N2—H2B	120.0	H46A—C46—H46B	108.0
H2A—N2—H2B	120.0	C4—N4—C41	126.5 (2)
C2—N3—C4	116.6 (2)	C4—N4—H4	116.7
N4—C4—N3	119.9 (3)	C41—N4—H4	116.7
N4—C4—C5	118.6 (3)	O5—N5—C5	117.0 (2)
N3—C4—C5	121.5 (2)	C6—O6—C67	118.4 (2)
N4—C41—C42	110.4 (2)	N5—C5—C6	116.7 (3)
N4—C41—C46	108.9 (2)	N5—C5—C4	128.4 (2)
C42—C41—C46	111.1 (2)	C6—C5—C4	114.9 (2)
N4—C41—H41	108.8	N1—C6—O6	120.2 (2)
C42—C41—H41	108.8	N1—C6—C5	123.8 (3)
C46—C41—H41	108.8	O6—C6—C5	115.9 (2)
C41—C42—C43	111.7 (3)	C62—C61—C66	118.4 (3)
C41—C42—H42A	109.3	C62—C61—C67	122.2 (3)
C43—C42—H42A	109.3	C66—C61—C67	119.4 (3)
C41—C42—H42B	109.3	C63—C62—C61	121.0 (3)
C43—C42—H42B	109.3	C63—C62—H62	119.5
H42A—C42—H42B	107.9	C61—C62—H62	119.5
C44—C43—C42	112.0 (3)	C62—C63—C64	120.1 (3)
C44—C43—H43A	109.2	C62—C63—H63	120.0
C42—C43—H43A	109.2	C64—C63—H63	120.0
C44—C43—H43B	109.2	C65—C64—C63	119.8 (3)
C42—C43—H43B	109.2	C65—C64—H64	120.1
H43A—C43—H43B	107.9	C63—C64—H64	120.1
C43—C44—C45	110.9 (3)	C64—C65—C66	120.1 (3)
C43—C44—H44A	109.5	C64—C65—H65	120.0
C45—C44—H44A	109.5	C66—C65—H65	120.0
C43—C44—H44B	109.5	C65—C66—C61	120.7 (3)
C45—C44—H44B	109.5	C65—C66—H66	119.6
H44A—C44—H44B	108.1	C61—C66—H66	119.6
C44—C45—C46	111.3 (3)	O6—C67—C61	111.4 (2)
C44—C45—H45A	109.4	O6—C67—H67A	109.4
C46—C45—H45A	109.4	C61—C67—H67A	109.4
C44—C45—H45B	109.4	O6—C67—H67B	109.4
C46—C45—H45B	109.4	C61—C67—H67B	109.4
H45A—C45—H45B	108.0	H67A—C67—H67B	108.0
C6—N1—C2—N2	−177.1 (3)	N4—C4—C5—C6	−176.3 (3)
C6—N1—C2—N3	3.7 (4)	N3—C4—C5—C6	3.5 (4)
N2—C2—N3—C4	178.9 (3)	C2—N1—C6—O6	179.5 (3)
N1—C2—N3—C4	−1.9 (5)	C2—N1—C6—C5	−1.6 (4)
C2—N3—C4—N4	177.9 (3)	C67—O6—C6—N1	−6.3 (4)
C2—N3—C4—C5	−1.9 (4)	C67—O6—C6—C5	174.8 (2)
N4—C41—C42—C43	−175.3 (2)	N5—C5—C6—N1	179.8 (3)
C46—C41—C42—C43	−54.4 (3)	C4—C5—C6—N1	−1.6 (4)
C41—C42—C43—C44	54.7 (4)	N5—C5—C6—O6	−1.3 (4)
C42—C43—C44—C45	−54.6 (4)	C4—C5—C6—O6	177.2 (2)
C43—C44—C45—C46	55.1 (3)	C66—C61—C62—C63	0.6 (4)
N4—C41—C46—C45	176.9 (2)	C67—C61—C62—C63	−176.7 (3)
C42—C41—C46—C45	55.1 (3)	C61—C62—C63—C64	−0.3 (5)
C44—C45—C46—C41	−55.7 (3)	C62—C63—C64—C65	0.1 (4)
N3—C4—N4—C41	−3.7 (5)	C63—C64—C65—C66	−0.2 (4)
C5—C4—N4—C41	176.1 (3)	C64—C65—C66—C61	0.4 (4)
C42—C41—N4—C4	−104.6 (3)	C62—C61—C66—C65	−0.6 (4)
C46—C41—N4—C4	133.2 (3)	C67—C61—C66—C65	176.7 (3)
O5—N5—C5—C6	178.6 (2)	C6—O6—C67—C61	106.7 (3)
O5—N5—C5—C4	0.3 (4)	C62—C61—C67—O6	−42.2 (4)
N4—C4—C5—N5	2.0 (5)	C66—C61—C67—O6	140.6 (3)
N3—C4—C5—N5	−178.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O5	0.88	1.91	2.609 (3)	135
N2—H2A···O5^i	0.88	1.99	2.804 (3)	153
C43—H43B···Cg1^ii	0.99	2.73	3.717 (4)	173

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

(5) 2-Amino-6-benzyloxy-4-(N-phenylamino)-5-nitrosopyrimidine

Crystal data

C17H15N5O2	Z = 1
Mr = 321.34	F(000) = 168
Triclinic, P1	Dx = 1.445 Mg m^−3
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.7622 (3) Å	Cell parameters from 2993 reflections
b = 5.8123 (4) Å	θ = 3.1–27.4°
c = 13.5635 (11) Å	µ = 0.10 mm^−1
α = 79.851 (2)°	T = 120 K
β = 87.346 (2)°	Plate, orange
γ = 89.692 (5)°	0.40 × 0.14 × 0.02 mm
V = 369.16 (5) Å^3

Data collection

Kappa-CCD diffractometer	2993 independent reflections
Radiation source: fine-focus sealed X-ray tube	2348 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.071
ϕ scans, and ω scans with κ offsets	θmax = 27.4°, θmin = 3.1°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −6→6
Tmin = 0.895, Tmax = 0.998	k = −7→7
5085 measured reflections	l = −17→17

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.136	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0712P)^2] where P = (Fo^2 + 2Fc^2)/3
2993 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.24 e Å^−3
3 restraints	Δρmin = −0.28 e Å^−3

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

	x	y	z	Uiso*/Ueq
O5	0.6912 (4)	0.6660 (4)	0.42918 (16)	0.0242 (5)
O6	0.8705 (4)	0.9113 (4)	0.66886 (15)	0.0220 (5)
N1	0.5250 (5)	1.1914 (4)	0.64857 (18)	0.0184 (5)
N2	0.1834 (5)	1.4673 (4)	0.62031 (19)	0.0214 (6)
N3	0.2449 (5)	1.2380 (4)	0.50086 (19)	0.0190 (6)
N4	0.3122 (5)	0.9852 (4)	0.38606 (18)	0.0196 (6)
N5	0.7492 (5)	0.7482 (4)	0.50760 (18)	0.0193 (6)
C2	0.3201 (6)	1.2946 (5)	0.5867 (2)	0.0168 (6)
C4	0.3793 (5)	1.0606 (5)	0.4697 (2)	0.0154 (6)
C5	0.6021 (6)	0.9377 (5)	0.5265 (2)	0.0170 (6)
C6	0.6623 (5)	1.0205 (5)	0.6159 (2)	0.0172 (6)
C41	0.1099 (6)	1.0710 (5)	0.3147 (2)	0.0189 (7)
C42	−0.0391 (6)	1.2776 (5)	0.3116 (2)	0.0216 (7)
C43	−0.2282 (6)	1.3425 (6)	0.2366 (2)	0.0252 (7)
C44	−0.2703 (6)	1.2034 (6)	0.1654 (2)	0.0256 (7)
C45	−0.1259 (6)	0.9967 (6)	0.1689 (2)	0.0274 (7)
C46	0.0648 (6)	0.9304 (6)	0.2431 (2)	0.0252 (7)
C61	0.6786 (6)	0.8086 (5)	0.8404 (2)	0.0213 (7)
C62	0.5716 (6)	0.5998 (6)	0.8193 (2)	0.0258 (7)
C63	0.3680 (7)	0.4723 (6)	0.8835 (3)	0.0364 (9)
C64	0.2753 (7)	0.5501 (7)	0.9694 (3)	0.0423 (10)
C65	0.3834 (7)	0.7516 (7)	0.9927 (3)	0.0402 (10)
C66	0.5845 (7)	0.8847 (6)	0.9278 (2)	0.0295 (8)
C67	0.8942 (6)	0.9502 (5)	0.7712 (2)	0.0208 (7)
H2A	0.0473	1.5407	0.5860	0.026*
H2B	0.2291	1.5083	0.6769	0.026*
H4	0.4083	0.8633	0.3732	0.023*
H42	−0.0123	1.3738	0.3603	0.026*
H43	−0.3300	1.4843	0.2341	0.030*
H44	−0.3989	1.2507	0.1143	0.031*
H45	−0.1563	0.8999	0.1208	0.033*
H46	0.1655	0.7882	0.2453	0.030*
H62	0.6382	0.5442	0.7607	0.031*
H63	0.2937	0.3324	0.8678	0.044*
H64	0.1358	0.4640	1.0129	0.051*
H65	0.3219	0.8016	1.0531	0.048*
H66	0.6555	1.0257	0.9435	0.035*
H67A	0.8668	1.1182	0.7734	0.025*
H67B	1.0848	0.9060	0.7938	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O5	0.0259 (11)	0.0267 (12)	0.0221 (12)	0.0076 (9)	−0.0039 (9)	−0.0100 (9)
O6	0.0225 (11)	0.0290 (12)	0.0148 (11)	0.0070 (9)	−0.0034 (8)	−0.0047 (9)
N1	0.0151 (11)	0.0225 (13)	0.0186 (13)	0.0047 (10)	−0.0035 (9)	−0.0061 (10)
N2	0.0200 (13)	0.0231 (14)	0.0222 (14)	0.0066 (10)	−0.0043 (10)	−0.0065 (11)
N3	0.0213 (13)	0.0171 (13)	0.0193 (14)	0.0032 (11)	−0.0011 (10)	−0.0055 (11)
N4	0.0224 (12)	0.0198 (14)	0.0176 (14)	0.0038 (10)	−0.0019 (10)	−0.0062 (11)
N5	0.0215 (13)	0.0200 (14)	0.0169 (13)	−0.0008 (11)	0.0029 (10)	−0.0060 (11)
C2	0.0161 (14)	0.0188 (16)	0.0154 (15)	0.0023 (11)	0.0004 (11)	−0.0032 (12)
C4	0.0108 (14)	0.0175 (15)	0.0173 (16)	0.0017 (11)	−0.0010 (11)	−0.0011 (12)
C5	0.0159 (15)	0.0168 (15)	0.0180 (16)	0.0005 (11)	−0.0005 (12)	−0.0022 (12)
C6	0.0150 (15)	0.0185 (15)	0.0172 (16)	−0.0026 (12)	0.0011 (11)	−0.0011 (12)
C41	0.0168 (14)	0.0236 (17)	0.0167 (16)	−0.0037 (12)	−0.0004 (12)	−0.0042 (13)
C42	0.0196 (15)	0.0258 (17)	0.0200 (17)	0.0048 (12)	−0.0051 (12)	−0.0045 (13)
C43	0.0204 (15)	0.0264 (18)	0.0285 (18)	0.0072 (12)	−0.0056 (12)	−0.0027 (15)
C44	0.0231 (16)	0.0333 (19)	0.0200 (17)	0.0004 (14)	−0.0094 (12)	−0.0018 (14)
C45	0.0329 (18)	0.0322 (19)	0.0199 (16)	−0.0051 (14)	−0.0038 (13)	−0.0116 (14)
C46	0.0289 (18)	0.0286 (18)	0.0200 (16)	0.0040 (14)	−0.0006 (13)	−0.0093 (14)
C61	0.0218 (15)	0.0257 (17)	0.0162 (15)	0.0049 (12)	−0.0050 (11)	−0.0027 (13)
C62	0.0268 (16)	0.0242 (17)	0.0265 (17)	0.0049 (13)	−0.0070 (13)	−0.0031 (14)
C63	0.033 (2)	0.0297 (19)	0.042 (2)	0.0003 (15)	−0.0099 (16)	0.0075 (16)
C64	0.0235 (18)	0.059 (3)	0.034 (2)	0.0045 (18)	0.0004 (15)	0.0188 (19)
C65	0.0355 (19)	0.064 (3)	0.0191 (18)	0.0122 (19)	0.0014 (14)	−0.0023 (18)
C66	0.0321 (18)	0.034 (2)	0.0231 (18)	0.0083 (15)	−0.0030 (13)	−0.0075 (15)
C67	0.0186 (14)	0.0274 (18)	0.0177 (15)	0.0055 (12)	−0.0112 (11)	−0.0049 (13)

Geometric parameters (Å, º)

O5—N5	1.282 (3)	C43—H43	0.9500
O6—C6	1.342 (3)	C44—C45	1.376 (4)
O6—C67	1.455 (3)	C44—H44	0.9500
N1—C6	1.316 (4)	C45—C46	1.390 (4)
N1—C2	1.382 (4)	C45—H45	0.9500
N2—C2	1.330 (4)	C46—H46	0.9500
N2—H2A	0.8800	C61—C66	1.391 (4)
N2—H2B	0.8800	C61—C62	1.399 (4)
N3—C2	1.328 (4)	C61—C67	1.503 (4)
N3—C4	1.332 (4)	C62—C63	1.396 (5)
N4—C4	1.338 (4)	C62—H62	0.9500
N4—C41	1.423 (4)	C63—C64	1.377 (5)
N4—H4	0.8800	C63—H63	0.9500
N5—C5	1.358 (4)	C64—C65	1.375 (6)
C4—C5	1.451 (4)	C64—H64	0.9500
C5—C6	1.423 (4)	C65—C66	1.408 (5)
C41—C42	1.387 (4)	C65—H65	0.9500
C41—C46	1.399 (4)	C66—H66	0.9500
C42—C43	1.392 (4)	C67—H67A	0.9900
C42—H42	0.9500	C67—H67B	0.9900
C43—C44	1.385 (4)
C6—O6—C67	117.7 (2)	C45—C44—H44	120.0
C6—N1—C2	114.7 (2)	C43—C44—H44	120.0
C2—N2—H2A	120.0	C44—C45—C46	119.6 (3)
C2—N2—H2B	120.0	C44—C45—H45	120.2
H2A—N2—H2B	120.0	C46—C45—H45	120.2
C2—N3—C4	117.3 (2)	C45—C46—C41	120.6 (3)
C4—N4—C41	130.2 (3)	C45—C46—H46	119.7
C4—N4—H4	114.9	C41—C46—H46	119.7
C41—N4—H4	114.9	C66—C61—C62	119.0 (3)
O5—N5—C5	117.4 (2)	C66—C61—C67	119.6 (3)
N3—C2—N2	118.2 (3)	C62—C61—C67	121.4 (3)
N3—C2—N1	127.7 (2)	C63—C62—C61	120.7 (3)
N2—C2—N1	114.1 (3)	C63—C62—H62	119.7
N3—C4—N4	121.8 (2)	C61—C62—H62	119.7
N3—C4—C5	121.0 (2)	C64—C63—C62	119.8 (3)
N4—C4—C5	117.2 (2)	C64—C63—H63	120.1
N5—C5—C6	116.5 (2)	C62—C63—H63	120.1
N5—C5—C4	128.2 (3)	C65—C64—C63	120.3 (3)
C6—C5—C4	115.2 (2)	C65—C64—H64	119.8
N1—C6—O6	119.8 (2)	C63—C64—H64	119.8
N1—C6—C5	124.0 (2)	C64—C65—C66	120.6 (3)
O6—C6—C5	116.2 (2)	C64—C65—H65	119.7
C42—C41—C46	119.5 (3)	C66—C65—H65	119.7
C42—C41—N4	125.3 (3)	C61—C66—C65	119.6 (3)
C46—C41—N4	115.2 (3)	C61—C66—H66	120.2
C41—C42—C43	119.3 (3)	C65—C66—H66	120.2
C41—C42—H42	120.4	O6—C67—C61	110.7 (2)
C43—C42—H42	120.4	O6—C67—H67A	109.5
C44—C43—C42	121.0 (3)	C61—C67—H67A	109.5
C44—C43—H43	119.5	O6—C67—H67B	109.5
C42—C43—H43	119.5	C61—C67—H67B	109.5
C45—C44—C43	120.0 (3)	H67A—C67—H67B	108.1

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O5	0.88	1.86	2.593 (3)	139
N2—H2A···N5^i	0.88	2.07	2.942 (3)	173
C42—H42···O5^i	0.95	2.48	3.215 (4)	133

Symmetry code: (i) x−1, y+1, z.

(7) 2-Amino-4-(N-butylamino)-6-(3-pyridyl)methoxy-5-nitrosopyrimidine

Crystal data

C14H18N6O2	F(000) = 1280
Mr = 302.33	Dx = 1.348 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3366 reflections
a = 28.3925 (6) Å	θ = 3.2–27.5°
b = 8.1627 (3) Å	µ = 0.10 mm^−1
c = 15.1540 (5) Å	T = 298 K
β = 121.9700 (13)°	Block, blue
V = 2979.39 (17) Å^3	0.22 × 0.08 × 0.03 mm
Z = 8

Data collection

Kappa-CCD diffractometer	1422 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tube	Rint = 0.065
Graphite monochromator	θmax = 27.5°, θmin = 3.2°
ϕ scans, and ω scans with κ offsets	h = −28→36
9945 measured reflections	k = −10→10
3366 independent reflections	l = −19→16

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.145	H-atom parameters constrained
S = 0.91	w = 1/[σ^2(Fo^2) + (0.0556P)^2] where P = (Fo^2 + 2Fc^2)/3
3366 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

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

	x	y	z	Uiso*/Ueq
N1	0.09435 (10)	0.6293 (2)	0.35945 (17)	0.0462 (6)
C2	0.11846 (12)	0.5643 (3)	0.4580 (2)	0.0438 (7)
N2	0.11195 (10)	0.6559 (3)	0.52305 (17)	0.0593 (7)
N3	0.14601 (10)	0.4235 (2)	0.49342 (16)	0.0444 (6)
N4	0.17926 (9)	0.1942 (3)	0.45739 (16)	0.0468 (6)
C5	0.12872 (11)	0.3883 (3)	0.31959 (19)	0.0387 (7)
N5	0.13250 (10)	0.3120 (3)	0.24433 (17)	0.0500 (6)
O5	0.15774 (8)	0.1743 (2)	0.26680 (14)	0.0608 (6)
C4	0.15148 (11)	0.3341 (3)	0.4253 (2)	0.0395 (7)
C41	0.20508 (12)	0.1292 (3)	0.5627 (2)	0.0487 (7)
C42	0.22718 (12)	−0.0406 (3)	0.5669 (2)	0.0484 (7)
C43	0.25527 (14)	−0.1174 (3)	0.6742 (2)	0.0557 (8)
C44	0.27919 (15)	−0.2858 (4)	0.6761 (3)	0.0740 (10)
C6	0.10045 (11)	0.5410 (3)	0.29452 (19)	0.0419 (7)
C61	0.04640 (12)	0.8031 (3)	0.0687 (2)	0.0446 (7)
C62	0.07416 (13)	0.9390 (3)	0.0682 (2)	0.0547 (8)
N63	0.07286 (11)	0.9978 (3)	−0.01612 (19)	0.0580 (7)
C64	0.04292 (13)	0.9130 (4)	−0.1035 (2)	0.0573 (8)
C65	0.01361 (13)	0.7776 (4)	−0.1114 (2)	0.0597 (9)
C66	0.01435 (13)	0.7223 (3)	−0.0246 (2)	0.0554 (8)
C67	0.05078 (14)	0.7497 (3)	0.1677 (2)	0.0596 (9)
O6	0.07952 (8)	0.5934 (2)	0.19662 (13)	0.0534 (6)
H2A	0.1253	0.6239	0.5860	0.071*
H2B	0.0943	0.7474	0.5023	0.071*
H4	0.1823	0.1375	0.4128	0.056*
H41A	0.1780	0.1252	0.5831	0.058*
H41B	0.2352	0.2005	0.6108	0.058*
H42A	0.2536	−0.0352	0.5449	0.058*
H42B	0.1967	−0.1103	0.5181	0.058*
H43A	0.2285	−0.1282	0.6952	0.067*
H43B	0.2849	−0.0462	0.7238	0.067*
H44A	0.2494	−0.3605	0.6339	0.111*
H44B	0.3001	−0.3255	0.7463	0.111*
H44C	0.3030	−0.2772	0.6492	0.111*
H62	0.0956	0.9951	0.1306	0.066*
H64	0.0421	0.9488	−0.1625	0.069*
H65	−0.0068	0.7223	−0.1744	0.072*
H66	−0.0066	0.6314	−0.0290	0.066*
H67A	0.0714	0.8300	0.2221	0.072*
H67B	0.0141	0.7382	0.1570	0.072*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0626 (17)	0.0455 (13)	0.0333 (14)	0.0074 (11)	0.0274 (13)	0.0034 (10)
C2	0.056 (2)	0.0457 (16)	0.0363 (17)	−0.0018 (14)	0.0289 (15)	−0.0013 (13)
N2	0.088 (2)	0.0569 (15)	0.0408 (15)	0.0185 (14)	0.0392 (15)	0.0061 (11)
N3	0.0541 (16)	0.0449 (13)	0.0363 (13)	0.0065 (11)	0.0254 (12)	0.0038 (10)
N4	0.0587 (16)	0.0461 (13)	0.0360 (13)	0.0071 (12)	0.0254 (12)	0.0034 (10)
C5	0.0457 (18)	0.0403 (15)	0.0324 (15)	−0.0003 (13)	0.0224 (14)	0.0003 (11)
N5	0.0584 (17)	0.0499 (14)	0.0400 (14)	0.0014 (12)	0.0248 (13)	−0.0046 (11)
O5	0.0769 (16)	0.0540 (12)	0.0481 (13)	0.0168 (11)	0.0306 (12)	−0.0011 (9)
C4	0.0445 (18)	0.0396 (15)	0.0375 (17)	−0.0035 (13)	0.0238 (14)	0.0014 (12)
C41	0.0515 (19)	0.0546 (17)	0.0366 (17)	0.0033 (14)	0.0210 (15)	0.0083 (12)
C42	0.054 (2)	0.0504 (16)	0.0403 (17)	0.0012 (14)	0.0242 (15)	0.0059 (13)
C43	0.067 (2)	0.0563 (18)	0.0454 (18)	0.0076 (15)	0.0312 (17)	0.0105 (13)
C44	0.095 (3)	0.067 (2)	0.064 (2)	0.024 (2)	0.044 (2)	0.0242 (17)
C6	0.0480 (19)	0.0447 (16)	0.0308 (16)	−0.0009 (14)	0.0193 (14)	0.0040 (12)
C61	0.0573 (19)	0.0400 (15)	0.0389 (17)	0.0105 (15)	0.0271 (15)	0.0077 (12)
C62	0.063 (2)	0.0526 (18)	0.0397 (18)	0.0029 (16)	0.0212 (16)	−0.0025 (13)
N63	0.0644 (18)	0.0558 (15)	0.0548 (17)	−0.0018 (13)	0.0323 (15)	0.0079 (13)
C64	0.065 (2)	0.066 (2)	0.043 (2)	0.0013 (17)	0.0301 (18)	0.0051 (15)
C65	0.075 (2)	0.0610 (19)	0.0417 (19)	−0.0074 (17)	0.0297 (17)	−0.0054 (14)
C66	0.073 (2)	0.0474 (16)	0.0500 (19)	−0.0086 (15)	0.0350 (18)	−0.0005 (14)
C67	0.090 (2)	0.0510 (17)	0.0494 (18)	0.0218 (16)	0.0443 (19)	0.0147 (14)
O6	0.0766 (15)	0.0471 (11)	0.0367 (12)	0.0172 (10)	0.0300 (11)	0.0099 (8)

Geometric parameters (Å, º)

N1—C6	1.303 (3)	C43—H43A	0.97
N1—C2	1.378 (3)	C43—H43B	0.97
C2—N2	1.326 (3)	C44—H44A	0.96
C2—N3	1.333 (3)	C44—H44B	0.96
N2—H2A	0.86	C44—H44C	0.96
N2—H2B	0.86	C6—O6	1.343 (3)
N3—C4	1.339 (3)	C61—C62	1.363 (4)
N4—C4	1.326 (3)	C61—C66	1.378 (4)
N4—C41	1.458 (3)	C61—C67	1.503 (4)
N4—H4	0.86	C62—N63	1.347 (3)
C5—N5	1.352 (3)	C62—H62	0.93
C5—C6	1.422 (3)	N63—C64	1.328 (3)
C5—C4	1.443 (3)	C64—C65	1.350 (4)
N5—O5	1.279 (3)	C64—H64	0.93
C41—C42	1.509 (3)	C65—C66	1.380 (4)
C41—H41A	0.97	C65—H65	0.93
C41—H41B	0.97	C66—H66	0.93
C42—C43	1.517 (4)	C67—O6	1.452 (3)
C42—H42A	0.97	C67—H67A	0.97
C42—H42B	0.97	C67—H67B	0.97
C43—C44	1.526 (4)
C6—N1—C2	114.7 (2)	C44—C43—H43B	109.3
N2—C2—N3	118.1 (2)	H43A—C43—H43B	108.0
N2—C2—N1	113.8 (2)	C43—C44—H44A	109.5
N3—C2—N1	128.1 (2)	C43—C44—H44B	109.5
C2—N2—H2A	120.0	H44A—C44—H44B	109.5
C2—N2—H2B	120.0	C43—C44—H44C	109.5
H2A—N2—H2B	120.0	H44A—C44—H44C	109.5
C2—N3—C4	116.3 (2)	H44B—C44—H44C	109.5
C4—N4—C41	124.9 (2)	N1—C6—O6	120.0 (2)
C4—N4—H4	117.6	N1—C6—C5	124.4 (2)
C41—N4—H4	117.6	O6—C6—C5	115.6 (2)
N5—C5—C6	117.6 (2)	C62—C61—C66	117.0 (2)
N5—C5—C4	127.3 (2)	C62—C61—C67	119.9 (2)
C6—C5—C4	115.0 (2)	C66—C61—C67	123.1 (3)
O5—N5—C5	117.6 (2)	N63—C62—C61	124.7 (3)
N4—C4—N3	118.4 (2)	N63—C62—H62	117.6
N4—C4—C5	120.1 (2)	C61—C62—H62	117.6
N3—C4—C5	121.5 (2)	C64—N63—C62	116.2 (3)
N4—C41—C42	109.7 (2)	N63—C64—C65	123.7 (3)
N4—C41—H41A	109.7	N63—C64—H64	118.1
C42—C41—H41A	109.7	C65—C64—H64	118.1
N4—C41—H41B	109.7	C64—C65—C66	119.0 (3)
C42—C41—H41B	109.7	C64—C65—H65	120.5
H41A—C41—H41B	108.2	C66—C65—H65	120.5
C41—C42—C43	113.3 (2)	C61—C66—C65	119.3 (3)
C41—C42—H42A	108.9	C61—C66—H66	120.3
C43—C42—H42A	108.9	C65—C66—H66	120.3
C41—C42—H42B	108.9	O6—C67—C61	107.0 (2)
C43—C42—H42B	108.9	O6—C67—H67A	110.3
H42A—C42—H42B	107.7	C61—C67—H67A	110.3
C42—C43—C44	111.6 (2)	O6—C67—H67B	110.3
C42—C43—H43A	109.3	C61—C67—H67B	110.3
C44—C43—H43A	109.3	H67A—C67—H67B	108.6
C42—C43—H43B	109.3	C6—O6—C67	117.57 (19)
C6—N1—C2—N2	179.9 (2)	C2—N1—C6—C5	0.8 (4)
C6—N1—C2—N3	−1.0 (4)	N5—C5—C6—N1	−178.9 (3)
N2—C2—N3—C4	179.7 (2)	C4—C5—C6—N1	−0.2 (4)
N1—C2—N3—C4	0.6 (4)	N5—C5—C6—O6	0.8 (3)
C6—C5—N5—O5	−179.7 (2)	C4—C5—C6—O6	179.4 (2)
C4—C5—N5—O5	1.9 (4)	C66—C61—C62—N63	−0.7 (4)
C41—N4—C4—N3	−0.4 (4)	C67—C61—C62—N63	−179.6 (3)
C41—N4—C4—C5	178.5 (2)	C61—C62—N63—C64	−1.4 (4)
C2—N3—C4—N4	179.0 (2)	C62—N63—C64—C65	1.8 (4)
C2—N3—C4—C5	0.1 (4)	N63—C64—C65—C66	−0.1 (5)
N5—C5—C4—N4	−0.7 (4)	C62—C61—C66—C65	2.5 (4)
C6—C5—C4—N4	−179.2 (2)	C67—C61—C66—C65	−178.6 (3)
N5—C5—C4—N3	178.2 (3)	C64—C65—C66—C61	−2.2 (5)
C6—C5—C4—N3	−0.2 (4)	C62—C61—C67—O6	−114.0 (3)
C4—N4—C41—C42	173.6 (2)	C66—C61—C67—O6	67.2 (4)
N4—C41—C42—C43	179.6 (2)	N1—C6—O6—C67	0.3 (4)
C41—C42—C43—C44	−177.5 (3)	C5—C6—O6—C67	−179.4 (2)
C2—N1—C6—O6	−178.9 (2)	C61—C67—O6—C6	163.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O5	0.86	1.96	2.622 (3)	133
N2—H2A···N5^i	0.86	2.36	3.095 (3)	144
N2—H2B···N63^ii	0.86	2.14	2.979 (3)	164
C62—H62···O5^iii	0.93	2.38	3.289 (3)	167

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

(8) 2-Amino-6-benzyloxy-4-piperidino-5-nitrosopyrimidine monohydrate

Crystal data

C16H19N5O2·H2O	F(000) = 704
Mr = 331.38	Dx = 1.347 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3658 reflections
a = 7.2557 (4) Å	θ = 2.9–27.4°
b = 11.4692 (7) Å	µ = 0.10 mm^−1
c = 20.4417 (15) Å	T = 120 K
β = 106.113 (3)°	Plate, purple
V = 1634.27 (18) Å^3	0.35 × 0.10 × 0.02 mm
Z = 4

Data collection

Kappa-CCD diffractometer	3658 independent reflections
Radiation source: fine-focus sealed X-ray tube	1996 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.094
ϕ scans, and ω scans with κ offsets	θmax = 27.4°, θmin = 2.9°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −9→9
Tmin = 0.956, Tmax = 0.998	k = −14→13
14044 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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.146	H-atom parameters constrained
S = 0.96	w = 1/[σ^2(Fo^2) + (0.0692P)^2] where P = (Fo^2 + 2Fc^2)/3
3658 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3

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

	x	y	z	Uiso*/Ueq
N1	0.7546 (3)	0.11594 (18)	0.19305 (10)	0.0218 (5)
C2	0.6003 (3)	0.0420 (2)	0.17565 (11)	0.0193 (5)
N2	0.4642 (2)	0.06307 (18)	0.20583 (10)	0.0237 (5)
N3	0.5709 (2)	−0.04385 (18)	0.12918 (9)	0.0210 (5)
N4	0.6710 (2)	−0.13078 (17)	0.04380 (9)	0.0203 (5)
C4	0.7119 (3)	−0.0656 (2)	0.09988 (11)	0.0181 (5)
C41	0.4782 (3)	−0.1816 (2)	0.01548 (12)	0.0253 (6)
C42	0.4937 (4)	−0.3048 (2)	−0.00936 (14)	0.0310 (6)
C43	0.6125 (4)	−0.3086 (2)	−0.06029 (14)	0.0347 (7)
C44	0.8075 (4)	−0.2505 (2)	−0.03168 (13)	0.0305 (6)
C45	0.7854 (3)	−0.1293 (2)	−0.00578 (12)	0.0244 (6)
C5	0.9028 (3)	−0.0174 (2)	0.13069 (11)	0.0183 (5)
N5	1.0750 (3)	−0.06937 (18)	0.14043 (9)	0.0211 (5)
O5	1.0783 (2)	−0.17172 (14)	0.11555 (8)	0.0250 (4)
C6	0.9019 (3)	0.0838 (2)	0.17257 (11)	0.0194 (5)
C61	1.0098 (3)	0.3537 (2)	0.20000 (13)	0.0284 (6)
C62	0.8268 (4)	0.3977 (2)	0.19198 (13)	0.0328 (6)
C63	0.7731 (4)	0.5022 (3)	0.15803 (14)	0.0396 (7)
C64	0.9025 (5)	0.5619 (3)	0.13168 (15)	0.0449 (8)
C65	1.0860 (5)	0.5184 (3)	0.13951 (15)	0.0460 (8)
C66	1.1389 (4)	0.4145 (3)	0.17433 (14)	0.0384 (7)
C67	1.0713 (3)	0.2432 (2)	0.23788 (13)	0.0281 (6)
O6	1.0636 (2)	0.14483 (15)	0.19078 (8)	0.0246 (4)
O1	0.5605 (2)	0.24413 (16)	0.31356 (9)	0.0345 (5)
H2A	0.3582	0.0214	0.1952	0.028*
H2B	0.4797	0.1188	0.2365	0.028*
H41A	0.4041	−0.1329	−0.0228	0.030*
H41B	0.4090	−0.1825	0.0510	0.030*
H42A	0.3636	−0.3355	−0.0312	0.037*
H42B	0.5540	−0.3555	0.0300	0.037*
H43A	0.5419	−0.2684	−0.1027	0.042*
H43B	0.6315	−0.3908	−0.0718	0.042*
H44A	0.8868	−0.2984	0.0060	0.037*
H44B	0.8745	−0.2459	−0.0677	0.037*
H45A	0.9138	−0.0963	0.0161	0.029*
H45B	0.7217	−0.0785	−0.0446	0.029*
H62	0.7382	0.3561	0.2098	0.039*
H63	0.6482	0.5328	0.1528	0.048*
H64	0.8653	0.6332	0.1081	0.054*
H65	1.1742	0.5593	0.1212	0.055*
H66	1.2649	0.3849	0.1806	0.046*
H67A	1.2039	0.2519	0.2676	0.034*
H67B	0.9865	0.2266	0.2673	0.034*
H1A	0.7023	0.2505	0.3341	0.041*
H1B	0.4960	0.3097	0.3307	0.041*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0150 (9)	0.0259 (12)	0.0238 (11)	0.0002 (8)	0.0042 (8)	−0.0016 (9)
C2	0.0147 (11)	0.0229 (14)	0.0196 (12)	0.0031 (10)	0.0034 (9)	0.0025 (10)
N2	0.0160 (9)	0.0274 (12)	0.0293 (11)	−0.0025 (8)	0.0090 (9)	−0.0075 (9)
N3	0.0170 (9)	0.0246 (12)	0.0221 (11)	0.0002 (8)	0.0065 (8)	−0.0013 (9)
N4	0.0160 (9)	0.0247 (12)	0.0199 (10)	−0.0026 (8)	0.0047 (8)	−0.0040 (9)
C4	0.0153 (11)	0.0190 (13)	0.0197 (12)	0.0014 (9)	0.0042 (9)	0.0036 (10)
C41	0.0178 (12)	0.0322 (16)	0.0232 (13)	−0.0019 (10)	0.0013 (10)	−0.0021 (11)
C42	0.0305 (14)	0.0302 (16)	0.0315 (15)	−0.0056 (11)	0.0074 (11)	−0.0048 (12)
C43	0.0348 (15)	0.0341 (18)	0.0348 (16)	−0.0026 (12)	0.0089 (12)	−0.0117 (13)
C44	0.0319 (13)	0.0352 (17)	0.0262 (14)	0.0003 (12)	0.0110 (11)	−0.0039 (12)
C45	0.0233 (12)	0.0306 (15)	0.0199 (13)	−0.0014 (11)	0.0070 (10)	0.0006 (11)
C5	0.0135 (11)	0.0236 (14)	0.0177 (12)	0.0001 (9)	0.0038 (9)	0.0027 (10)
N5	0.0195 (10)	0.0229 (12)	0.0221 (10)	0.0003 (8)	0.0079 (8)	−0.0004 (9)
O5	0.0236 (8)	0.0215 (10)	0.0297 (10)	0.0031 (7)	0.0071 (7)	−0.0042 (8)
C6	0.0157 (11)	0.0226 (14)	0.0193 (12)	−0.0010 (9)	0.0038 (9)	0.0036 (10)
C61	0.0299 (13)	0.0279 (15)	0.0292 (14)	−0.0073 (11)	0.0116 (11)	−0.0103 (12)
C62	0.0335 (14)	0.0313 (16)	0.0314 (15)	−0.0054 (12)	0.0055 (12)	−0.0047 (13)
C63	0.0438 (16)	0.0340 (18)	0.0365 (16)	0.0016 (13)	0.0035 (13)	−0.0031 (14)
C64	0.065 (2)	0.0322 (18)	0.0349 (16)	−0.0062 (15)	0.0086 (15)	−0.0001 (14)
C65	0.063 (2)	0.040 (2)	0.0393 (17)	−0.0145 (16)	0.0210 (15)	−0.0042 (15)
C66	0.0399 (16)	0.0402 (19)	0.0389 (16)	−0.0101 (14)	0.0171 (13)	−0.0107 (14)
C67	0.0218 (12)	0.0296 (16)	0.0317 (14)	−0.0019 (11)	0.0052 (11)	−0.0111 (12)
O6	0.0162 (8)	0.0248 (10)	0.0334 (10)	−0.0027 (7)	0.0080 (7)	−0.0081 (8)
O1	0.0191 (8)	0.0381 (12)	0.0453 (11)	−0.0002 (8)	0.0077 (8)	−0.0184 (9)

Geometric parameters (Å, º)

N1—C6	1.305 (3)	C45—H45A	0.99
N1—C2	1.371 (3)	C45—H45B	0.99
C2—N2	1.324 (3)	C5—N5	1.348 (3)
C2—N3	1.343 (3)	C5—C6	1.443 (3)
N2—H2A	0.88	N5—O5	1.282 (2)
N2—H2B	0.88	C6—O6	1.328 (3)
N3—C4	1.345 (3)	C61—C66	1.383 (4)
N4—C4	1.331 (3)	C61—C62	1.387 (4)
N4—C41	1.477 (3)	C61—C67	1.488 (4)
N4—C45	1.477 (3)	C62—C63	1.386 (4)
C4—C5	1.461 (3)	C62—H62	0.95
C41—C42	1.517 (4)	C63—C64	1.386 (4)
C41—H41A	0.99	C63—H63	0.95
C41—H41B	0.99	C64—C65	1.389 (4)
C42—C43	1.525 (4)	C64—H64	0.95
C42—H42A	0.99	C65—C66	1.386 (4)
C42—H42B	0.99	C65—H65	0.95
C43—C44	1.526 (4)	C66—H66	0.95
C43—H43A	0.99	C67—O6	1.474 (3)
C43—H43B	0.99	C67—H67A	0.99
C44—C45	1.512 (4)	C67—H67B	0.99
C44—H44A	0.99	O1—H1A	1.00
C44—H44B	0.99	O1—H1B	1.00
C6—N1—C2	115.1 (2)	N4—C45—H45A	109.4
N2—C2—N3	118.1 (2)	C44—C45—H45A	109.4
N2—C2—N1	115.3 (2)	N4—C45—H45B	109.4
N3—C2—N1	126.52 (19)	C44—C45—H45B	109.4
C2—N2—H2A	120.0	H45A—C45—H45B	108.0
C2—N2—H2B	120.0	N5—C5—C6	115.10 (19)
H2A—N2—H2B	120.0	N5—C5—C4	128.7 (2)
C2—N3—C4	117.38 (19)	C6—C5—C4	113.61 (18)
C4—N4—C41	121.30 (18)	O5—N5—C5	117.68 (18)
C4—N4—C45	123.44 (18)	N1—C6—O6	120.0 (2)
C41—N4—C45	112.75 (18)	N1—C6—C5	123.8 (2)
N4—C4—N3	118.19 (19)	O6—C6—C5	116.19 (18)
N4—C4—C5	122.81 (19)	C66—C61—C62	119.9 (3)
N3—C4—C5	119.0 (2)	C66—C61—C67	119.4 (2)
N4—C41—C42	110.41 (19)	C62—C61—C67	120.7 (2)
N4—C41—H41A	109.6	C63—C62—C61	120.0 (3)
C42—C41—H41A	109.6	C63—C62—H62	120.0
N4—C41—H41B	109.6	C61—C62—H62	120.0
C42—C41—H41B	109.6	C62—C63—C64	119.7 (3)
H41A—C41—H41B	108.1	C62—C63—H63	120.2
C41—C42—C43	111.3 (2)	C64—C63—H63	120.2
C41—C42—H42A	109.4	C63—C64—C65	120.6 (3)
C43—C42—H42A	109.4	C63—C64—H64	119.7
C41—C42—H42B	109.4	C65—C64—H64	119.7
C43—C42—H42B	109.4	C66—C65—C64	119.2 (3)
H42A—C42—H42B	108.0	C66—C65—H65	120.4
C42—C43—C44	111.4 (2)	C64—C65—H65	120.4
C42—C43—H43A	109.3	C61—C66—C65	120.5 (3)
C44—C43—H43A	109.3	C61—C66—H66	119.7
C42—C43—H43B	109.3	C65—C66—H66	119.7
C44—C43—H43B	109.3	O6—C67—C61	111.1 (2)
H43A—C43—H43B	108.0	O6—C67—H67A	109.4
C45—C44—C43	111.0 (2)	C61—C67—H67A	109.4
C45—C44—H44A	109.4	O6—C67—H67B	109.4
C43—C44—H44A	109.4	C61—C67—H67B	109.4
C45—C44—H44B	109.4	H67A—C67—H67B	108.0
C43—C44—H44B	109.4	C6—O6—C67	117.19 (17)
H44A—C44—H44B	108.0	H1A—O1—H1B	109.0
N4—C45—C44	111.3 (2)
C6—N1—C2—N2	168.9 (2)	C6—C5—N5—O5	166.00 (19)
C6—N1—C2—N3	−14.8 (3)	C4—C5—N5—O5	5.8 (3)
N2—C2—N3—C4	−178.8 (2)	C2—N1—C6—O6	−175.3 (2)
N1—C2—N3—C4	5.1 (3)	C2—N1—C6—C5	4.1 (3)
C41—N4—C4—N3	−2.1 (3)	N5—C5—C6—N1	−149.7 (2)
C45—N4—C4—N3	158.6 (2)	C4—C5—C6—N1	13.5 (3)
C41—N4—C4—C5	177.8 (2)	N5—C5—C6—O6	29.6 (3)
C45—N4—C4—C5	−21.5 (3)	C4—C5—C6—O6	−167.10 (19)
C2—N3—C4—N4	−165.3 (2)	C66—C61—C62—C63	0.3 (4)
C2—N3—C4—C5	14.8 (3)	C67—C61—C62—C63	178.4 (2)
C4—N4—C41—C42	−139.7 (2)	C61—C62—C63—C64	0.5 (4)
C45—N4—C41—C42	57.7 (3)	C62—C63—C64—C65	−0.6 (4)
N4—C41—C42—C43	−55.0 (3)	C63—C64—C65—C66	−0.3 (4)
C41—C42—C43—C44	53.1 (3)	C62—C61—C66—C65	−1.1 (4)
C42—C43—C44—C45	−52.3 (3)	C67—C61—C66—C65	−179.3 (2)
C4—N4—C45—C44	140.2 (2)	C64—C65—C66—C61	1.1 (4)
C41—N4—C45—C44	−57.6 (3)	C66—C61—C67—O6	−80.7 (3)
C43—C44—C45—N4	54.1 (3)	C62—C61—C67—O6	101.2 (3)
N4—C4—C5—N5	−42.6 (3)	N1—C6—O6—C67	4.0 (3)
N3—C4—C5—N5	137.3 (2)	C5—C6—O6—C67	−175.37 (19)
N4—C4—C5—C6	156.9 (2)	C61—C67—O6—C6	−91.7 (2)
N3—C4—C5—C6	−23.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N5^i	0.88	2.30	3.158 (3)	165
N2—H2B···O1	0.88	2.09	2.966 (3)	171
O1—H1A···O5^ii	1.00	1.87	2.791 (2)	153
O1—H1B···N3^iii	1.00	1.99	2.968 (3)	167

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

(9) 2-Amino-6-benzyloxy-4-piperidino-pyrimidine

Crystal data

C16H20N4O	Z = 4
Mr = 284.36	F(000) = 608
Triclinic, P1	Dx = 1.255 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.5025 (2) Å	Cell parameters from 6307 reflections
b = 11.8006 (4) Å	θ = 3.2–27.4°
c = 20.7673 (10) Å	µ = 0.08 mm^−1
α = 76.1950 (14)°	T = 120 K
β = 82.3623 (14)°	Needle, colourless
γ = 77.330 (4)°	0.70 × 0.17 × 0.08 mm
V = 1504.36 (10) Å^3

Data collection

Kappa-CCD diffractometer	6307 independent reflections
Radiation source: fine-focus sealed X-ray tube	4163 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
ϕ scans, and ω scans with κ offsets	θmax = 27.4°, θmin = 3.2°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −7→8
Tmin = 0.965, Tmax = 0.994	k = −15→15
17141 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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.161	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0891P)^2 + 0.0112P] where P = (Fo^2 + 2Fc^2)/3
6307 reflections	(Δ/σ)max < 0.001
379 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.37 e Å^−3

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

	x	y	z	Uiso*/Ueq
N11	0.0110 (2)	0.75322 (13)	0.15351 (7)	0.0218 (4)
C12	0.1444 (3)	0.71274 (16)	0.20260 (9)	0.0200 (4)
N12	0.0955 (2)	0.76122 (14)	0.25623 (7)	0.0242 (4)
N13	0.3227 (2)	0.63035 (13)	0.20232 (7)	0.0210 (4)
C14	0.3809 (3)	0.58490 (16)	0.14718 (9)	0.0205 (4)
C141	0.6447 (3)	0.44842 (19)	0.09084 (10)	0.0314 (5)
C142	0.8839 (3)	0.41727 (19)	0.08266 (10)	0.0309 (5)
C143	0.9775 (3)	0.34666 (19)	0.14661 (10)	0.0331 (5)
C144	0.8957 (3)	0.41368 (18)	0.20221 (10)	0.0289 (5)
C145	0.6577 (3)	0.43967 (18)	0.21006 (9)	0.0272 (4)
N14	0.5695 (2)	0.50642 (14)	0.14686 (7)	0.0260 (4)
C15	0.2541 (3)	0.62060 (16)	0.09391 (9)	0.0227 (4)
C16	0.0735 (3)	0.70490 (16)	0.10060 (9)	0.0216 (4)
C161	−0.3168 (3)	0.86833 (17)	−0.01596 (9)	0.0248 (4)
C162	−0.4927 (3)	0.83524 (18)	−0.03119 (10)	0.0292 (5)
C163	−0.5641 (3)	0.87643 (18)	−0.09436 (10)	0.0327 (5)
C164	−0.4591 (3)	0.95021 (18)	−0.14270 (10)	0.0350 (5)
C167	−0.2415 (3)	0.82596 (19)	0.05286 (9)	0.0314 (5)
C165	−0.2834 (3)	0.98416 (19)	−0.12790 (10)	0.0357 (5)
C166	−0.2134 (3)	0.94322 (18)	−0.06497 (10)	0.0315 (5)
O16	−0.0472 (2)	0.73968 (12)	0.04816 (6)	0.0280 (3)
N21	0.4331 (2)	0.75792 (13)	0.34964 (7)	0.0214 (4)
C22	0.5693 (3)	0.80224 (16)	0.29988 (9)	0.0206 (4)
N22	0.6007 (2)	0.75660 (14)	0.24529 (7)	0.0262 (4)
N23	0.6787 (2)	0.88644 (13)	0.29946 (7)	0.0211 (4)
C24	0.6589 (3)	0.92879 (16)	0.35557 (9)	0.0212 (4)
C241	0.7761 (3)	1.06592 (18)	0.41072 (9)	0.0276 (5)
C242	0.9988 (3)	1.07798 (17)	0.41893 (9)	0.0256 (4)
C243	1.1009 (3)	1.14397 (18)	0.35516 (10)	0.0286 (5)
C244	1.0937 (3)	1.08613 (18)	0.29770 (9)	0.0264 (4)
C245	0.8687 (3)	1.07606 (17)	0.29146 (9)	0.0258 (4)
N24	0.7767 (3)	1.01184 (14)	0.35427 (7)	0.0260 (4)
C25	0.5279 (3)	0.88589 (16)	0.41094 (9)	0.0228 (4)
C26	0.4195 (3)	0.80179 (16)	0.40391 (9)	0.0208 (4)
C261	0.0675 (3)	0.62977 (17)	0.51869 (9)	0.0249 (4)
C262	0.1903 (3)	0.55205 (18)	0.56661 (10)	0.0326 (5)
C263	0.0977 (4)	0.50528 (19)	0.62860 (10)	0.0361 (5)
C264	−0.1172 (4)	0.53597 (19)	0.64308 (10)	0.0354 (5)
C265	−0.2405 (3)	0.61248 (19)	0.59580 (10)	0.0330 (5)
C266	−0.1483 (3)	0.65875 (18)	0.53380 (10)	0.0293 (5)
C267	0.1669 (3)	0.6775 (2)	0.45064 (10)	0.0333 (5)
O26	0.2895 (2)	0.76187 (12)	0.45754 (6)	0.0267 (3)
H12A	0.1791	0.7385	0.2889	0.029*
H12B	−0.0200	0.8157	0.2588	0.029*
H14A	0.5921	0.5021	0.0495	0.038*
H14B	0.5869	0.3750	0.0982	0.038*
H14C	0.9404	0.4915	0.0676	0.037*
H14D	0.9281	0.3703	0.0478	0.037*
H14E	1.1338	0.3347	0.1403	0.040*
H14F	0.9374	0.2676	0.1588	0.040*
H14G	0.9506	0.3653	0.2445	0.035*
H14H	0.9480	0.4893	0.1918	0.035*
H14I	0.6059	0.3639	0.2248	0.033*
H14J	0.6082	0.4867	0.2447	0.033*
H15	0.2904	0.5885	0.0552	0.027*
H162	−0.5654	0.7839	0.0018	0.035*
H163	−0.6858	0.8536	−0.1042	0.039*
H164	−0.5071	0.9777	−0.1860	0.042*
H16A	−0.2160	0.8936	0.0691	0.038*
H16B	−0.3491	0.7890	0.0842	0.038*
H165	−0.2110	1.0356	−0.1610	0.043*
H166	−0.0925	0.9668	−0.0552	0.038*
H22A	0.6891	0.7822	0.2118	0.031*
H22B	0.5329	0.7010	0.2429	0.031*
H24A	0.7200	1.0160	0.4518	0.033*
H24B	0.6825	1.1454	0.4035	0.033*
H24C	0.9932	1.1212	0.4547	0.031*
H24D	1.0867	0.9978	0.4325	0.031*
H24E	1.2498	1.1432	0.3611	0.034*
H24F	1.0255	1.2279	0.3449	0.034*
H24G	1.1490	1.1343	0.2558	0.032*
H24H	1.1849	1.0059	0.3052	0.032*
H24I	0.7812	1.1567	0.2790	0.031*
H24J	0.8684	1.0335	0.2557	0.031*
H25	0.5142	0.9131	0.4511	0.027*
H262	0.3388	0.5307	0.5569	0.039*
H263	0.1828	0.4520	0.6611	0.043*
H264	−0.1803	0.5044	0.6857	0.042*
H265	−0.3890	0.6336	0.6057	0.040*
H266	−0.2346	0.7111	0.5012	0.035*
H26A	0.2596	0.6118	0.4325	0.040*
H26B	0.0560	0.7171	0.4198	0.040*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0261 (9)	0.0242 (9)	0.0153 (8)	−0.0056 (6)	−0.0008 (6)	−0.0046 (7)
C12	0.0210 (10)	0.0238 (10)	0.0170 (9)	−0.0097 (7)	0.0021 (7)	−0.0047 (8)
N12	0.0225 (9)	0.0331 (10)	0.0181 (8)	−0.0011 (7)	−0.0017 (6)	−0.0119 (7)
N13	0.0220 (9)	0.0247 (9)	0.0158 (8)	−0.0042 (6)	0.0009 (6)	−0.0051 (7)
C14	0.0269 (10)	0.0204 (10)	0.0150 (9)	−0.0077 (8)	0.0016 (7)	−0.0043 (7)
C141	0.0387 (12)	0.0340 (12)	0.0224 (11)	0.0025 (9)	−0.0064 (8)	−0.0147 (9)
C142	0.0355 (12)	0.0353 (12)	0.0205 (10)	0.0004 (9)	−0.0020 (8)	−0.0099 (9)
C143	0.0321 (12)	0.0370 (12)	0.0264 (11)	0.0030 (9)	−0.0044 (8)	−0.0074 (9)
C144	0.0331 (12)	0.0309 (11)	0.0202 (10)	−0.0016 (8)	−0.0072 (8)	−0.0025 (9)
C145	0.0340 (12)	0.0251 (11)	0.0199 (10)	−0.0018 (8)	−0.0041 (8)	−0.0025 (8)
N14	0.0305 (9)	0.0291 (9)	0.0162 (8)	0.0040 (7)	−0.0056 (6)	−0.0076 (7)
C15	0.0290 (11)	0.0247 (10)	0.0145 (9)	−0.0038 (8)	0.0002 (7)	−0.0067 (8)
C16	0.0265 (10)	0.0235 (10)	0.0149 (9)	−0.0064 (8)	−0.0011 (7)	−0.0030 (8)
C161	0.0283 (11)	0.0239 (11)	0.0193 (10)	0.0006 (8)	−0.0009 (8)	−0.0048 (8)
C162	0.0338 (12)	0.0252 (11)	0.0253 (11)	−0.0043 (8)	−0.0007 (8)	−0.0015 (9)
C163	0.0320 (12)	0.0334 (12)	0.0340 (12)	−0.0014 (9)	−0.0095 (9)	−0.0105 (10)
C164	0.0478 (14)	0.0302 (12)	0.0215 (11)	0.0062 (10)	−0.0079 (9)	−0.0045 (9)
C167	0.0303 (12)	0.0378 (12)	0.0217 (11)	0.0065 (9)	−0.0051 (8)	−0.0084 (9)
C165	0.0445 (14)	0.0317 (12)	0.0253 (11)	−0.0079 (10)	0.0056 (9)	0.0005 (9)
C166	0.0320 (12)	0.0354 (12)	0.0295 (12)	−0.0083 (9)	−0.0001 (9)	−0.0116 (10)
O16	0.0285 (8)	0.0347 (8)	0.0193 (7)	0.0038 (6)	−0.0069 (5)	−0.0094 (6)
N21	0.0244 (9)	0.0238 (9)	0.0156 (8)	−0.0034 (6)	−0.0014 (6)	−0.0050 (6)
C22	0.0212 (10)	0.0226 (10)	0.0161 (9)	0.0008 (7)	−0.0035 (7)	−0.0041 (8)
N22	0.0297 (9)	0.0350 (10)	0.0187 (8)	−0.0128 (7)	0.0038 (6)	−0.0120 (7)
N23	0.0224 (9)	0.0258 (9)	0.0156 (8)	−0.0037 (6)	−0.0022 (6)	−0.0060 (7)
C24	0.0225 (10)	0.0235 (10)	0.0157 (9)	−0.0009 (8)	−0.0038 (7)	−0.0031 (8)
C241	0.0345 (12)	0.0317 (12)	0.0186 (10)	−0.0075 (9)	0.0009 (8)	−0.0101 (9)
C242	0.0341 (12)	0.0243 (11)	0.0199 (10)	−0.0059 (8)	−0.0030 (8)	−0.0070 (8)
C243	0.0344 (12)	0.0261 (11)	0.0269 (11)	−0.0100 (9)	−0.0047 (8)	−0.0037 (9)
C244	0.0303 (11)	0.0264 (11)	0.0206 (10)	−0.0065 (8)	0.0006 (8)	−0.0022 (8)
C245	0.0334 (11)	0.0256 (11)	0.0178 (10)	−0.0077 (8)	−0.0010 (8)	−0.0019 (8)
N24	0.0340 (10)	0.0312 (10)	0.0162 (8)	−0.0131 (7)	0.0035 (6)	−0.0087 (7)
C25	0.0291 (11)	0.0234 (10)	0.0159 (9)	−0.0034 (8)	−0.0015 (7)	−0.0062 (8)
C26	0.0227 (10)	0.0215 (10)	0.0146 (9)	−0.0013 (7)	−0.0009 (7)	−0.0002 (8)
C261	0.0338 (12)	0.0254 (11)	0.0187 (10)	−0.0134 (8)	−0.0002 (8)	−0.0050 (8)
C262	0.0350 (12)	0.0354 (12)	0.0292 (12)	−0.0056 (9)	−0.0055 (9)	−0.0103 (10)
C263	0.0572 (15)	0.0267 (12)	0.0236 (11)	−0.0063 (10)	−0.0133 (10)	−0.0006 (9)
C264	0.0546 (15)	0.0325 (12)	0.0224 (11)	−0.0213 (10)	0.0047 (9)	−0.0049 (9)
C265	0.0335 (12)	0.0344 (12)	0.0350 (12)	−0.0140 (9)	0.0046 (9)	−0.0126 (10)
C266	0.0398 (12)	0.0245 (11)	0.0252 (11)	−0.0088 (9)	−0.0074 (8)	−0.0035 (9)
C267	0.0464 (13)	0.0382 (12)	0.0222 (11)	−0.0238 (10)	0.0030 (9)	−0.0088 (9)
O26	0.0326 (8)	0.0318 (8)	0.0182 (7)	−0.0139 (6)	0.0052 (5)	−0.0073 (6)

Geometric parameters (Å, º)

N11—C16	1.333 (2)	N21—C26	1.333 (2)
N11—C12	1.357 (2)	N21—C22	1.352 (2)
C12—N13	1.341 (2)	C22—N23	1.340 (2)
C12—N12	1.341 (2)	C22—N22	1.341 (2)
N12—H12A	0.88	N22—H22A	0.88
N12—H12B	0.88	N22—H22B	0.88
N13—C14	1.353 (2)	N23—C24	1.354 (2)
C14—N14	1.365 (2)	C24—N24	1.364 (2)
C14—C15	1.396 (3)	C24—C25	1.398 (3)
C141—N14	1.464 (2)	C241—N24	1.461 (2)
C141—C142	1.514 (3)	C241—C242	1.521 (3)
C141—H14A	0.99	C241—H24A	0.99
C141—H14B	0.99	C241—H24B	0.99
C142—C143	1.514 (3)	C242—C243	1.517 (3)
C142—H14C	0.99	C242—H24C	0.99
C142—H14D	0.99	C242—H24D	0.99
C143—C144	1.526 (3)	C243—C244	1.520 (3)
C143—H14E	0.99	C243—H24E	0.99
C143—H14F	0.99	C243—H24F	0.99
C144—C145	1.505 (3)	C244—C245	1.518 (3)
C144—H14G	0.99	C244—H24G	0.99
C144—H14H	0.99	C244—H24H	0.99
C145—N14	1.477 (2)	C245—N24	1.467 (2)
C145—H14I	0.99	C245—H24I	0.99
C145—H14J	0.99	C245—H24J	0.99
C15—C16	1.378 (3)	C25—C26	1.381 (3)
C15—H15	0.95	C25—H25	0.95
C16—O16	1.357 (2)	C26—O26	1.361 (2)
C161—C162	1.383 (3)	C261—C266	1.381 (3)
C161—C166	1.385 (3)	C261—C262	1.387 (3)
C161—C167	1.507 (3)	C261—C267	1.506 (3)
C162—C163	1.390 (3)	C262—C263	1.388 (3)
C162—H162	0.95	C262—H262	0.95
C163—C164	1.376 (3)	C263—C264	1.376 (3)
C163—H163	0.95	C263—H263	0.95
C164—C165	1.383 (3)	C264—C265	1.375 (3)
C164—H164	0.95	C264—H264	0.95
C167—O16	1.447 (2)	C265—C266	1.385 (3)
C167—H16A	0.99	C265—H265	0.95
C167—H16B	0.99	C266—H266	0.95
C165—C166	1.382 (3)	C267—O26	1.447 (2)
C165—H165	0.95	C267—H26A	0.99
C166—H166	0.95	C267—H26B	0.99
C16—N11—C12	113.87 (15)	C26—N21—C22	113.65 (15)
N13—C12—N12	116.59 (15)	N23—C22—N22	116.24 (15)
N13—C12—N11	126.37 (16)	N23—C22—N21	126.91 (16)
N12—C12—N11	117.02 (16)	N22—C22—N21	116.84 (16)
C12—N12—H12A	120.0	C22—N22—H22A	120.0
C12—N12—H12B	120.0	C22—N22—H22B	120.0
H12A—N12—H12B	120.0	H22A—N22—H22B	120.0
C12—N13—C14	117.57 (15)	C22—N23—C24	117.22 (15)
N13—C14—N14	116.15 (15)	N23—C24—N24	115.83 (15)
N13—C14—C15	120.44 (16)	N23—C24—C25	120.55 (16)
N14—C14—C15	123.38 (16)	N24—C24—C25	123.61 (16)
N14—C141—C142	111.59 (16)	N24—C241—C242	110.51 (15)
N14—C141—H14A	109.3	N24—C241—H24A	109.5
C142—C141—H14A	109.3	C242—C241—H24A	109.5
N14—C141—H14B	109.3	N24—C241—H24B	109.5
C142—C141—H14B	109.3	C242—C241—H24B	109.5
H14A—C141—H14B	108.0	H24A—C241—H24B	108.1
C141—C142—C143	112.36 (17)	C243—C242—C241	111.91 (16)
C141—C142—H14C	109.1	C243—C242—H24C	109.2
C143—C142—H14C	109.1	C241—C242—H24C	109.2
C141—C142—H14D	109.1	C243—C242—H24D	109.2
C143—C142—H14D	109.1	C241—C242—H24D	109.2
H14C—C142—H14D	107.9	H24C—C242—H24D	107.9
C142—C143—C144	109.57 (16)	C242—C243—C244	110.49 (16)
C142—C143—H14E	109.8	C242—C243—H24E	109.6
C144—C143—H14E	109.8	C244—C243—H24E	109.6
C142—C143—H14F	109.8	C242—C243—H24F	109.6
C144—C143—H14F	109.8	C244—C243—H24F	109.6
H14E—C143—H14F	108.2	H24E—C243—H24F	108.1
C145—C144—C143	110.81 (16)	C245—C244—C243	110.62 (15)
C145—C144—H14G	109.5	C245—C244—H24G	109.5
C143—C144—H14G	109.5	C243—C244—H24G	109.5
C145—C144—H14H	109.5	C245—C244—H24H	109.5
C143—C144—H14H	109.5	C243—C244—H24H	109.5
H14G—C144—H14H	108.1	H24G—C244—H24H	108.1
N14—C145—C144	111.14 (16)	N24—C245—C244	110.98 (15)
N14—C145—H14I	109.4	N24—C245—H24I	109.4
C144—C145—H14I	109.4	C244—C245—H24I	109.4
N14—C145—H14J	109.4	N24—C245—H24J	109.4
C144—C145—H14J	109.4	C244—C245—H24J	109.4
H14I—C145—H14J	108.0	H24I—C245—H24J	108.0
C14—N14—C141	120.90 (15)	C24—N24—C241	123.04 (15)
C14—N14—C145	120.41 (15)	C24—N24—C245	121.54 (15)
C141—N14—C145	113.93 (15)	C241—N24—C245	113.58 (15)
C16—C15—C14	116.37 (17)	C26—C25—C24	116.20 (17)
C16—C15—H15	121.8	C26—C25—H25	121.9
C14—C15—H15	121.8	C24—C25—H25	121.9
N11—C16—O16	118.92 (16)	N21—C26—O26	118.65 (16)
N11—C16—C15	125.34 (17)	N21—C26—C25	125.39 (16)
O16—C16—C15	115.74 (16)	O26—C26—C25	115.96 (16)
C162—C161—C166	118.60 (18)	C266—C261—C262	118.68 (18)
C162—C161—C167	120.79 (17)	C266—C261—C267	120.79 (18)
C166—C161—C167	120.60 (19)	C262—C261—C267	120.48 (19)
C161—C162—C163	120.63 (19)	C261—C262—C263	120.5 (2)
C161—C162—H162	119.7	C261—C262—H262	119.8
C163—C162—H162	119.7	C263—C262—H262	119.8
C164—C163—C162	120.2 (2)	C264—C263—C262	120.13 (19)
C164—C163—H163	119.9	C264—C263—H263	119.9
C162—C163—H163	119.9	C262—C263—H263	119.9
C163—C164—C165	119.67 (19)	C265—C264—C263	119.88 (19)
C163—C164—H164	120.2	C265—C264—H264	120.1
C165—C164—H164	120.2	C263—C264—H264	120.1
O16—C167—C161	107.02 (15)	C264—C265—C266	120.0 (2)
O16—C167—H16A	110.3	C264—C265—H265	120.0
C161—C167—H16A	110.3	C266—C265—H265	120.0
O16—C167—H16B	110.3	C261—C266—C265	120.84 (19)
C161—C167—H16B	110.3	C261—C266—H266	119.6
H16A—C167—H16B	108.6	C265—C266—H266	119.6
C166—C165—C164	119.94 (19)	O26—C267—C261	107.60 (15)
C166—C165—H165	120.0	O26—C267—H26A	110.2
C164—C165—H165	120.0	C261—C267—H26A	110.2
C165—C166—C161	121.0 (2)	O26—C267—H26B	110.2
C165—C166—H166	119.5	C261—C267—H26B	110.2
C161—C166—H166	119.5	H26A—C267—H26B	108.5
C16—O16—C167	118.32 (14)	C26—O26—C267	117.20 (14)
C16—N11—C12—N13	−1.3 (3)	C26—N21—C22—N23	−3.3 (3)
C16—N11—C12—N12	177.36 (16)	C26—N21—C22—N22	176.00 (15)
N12—C12—N13—C14	−176.54 (15)	N22—C22—N23—C24	−176.24 (15)
N11—C12—N13—C14	2.2 (3)	N21—C22—N23—C24	3.0 (3)
C12—N13—C14—N14	176.31 (16)	C22—N23—C24—N24	178.18 (16)
C12—N13—C14—C15	−2.1 (2)	C22—N23—C24—C25	−0.4 (2)
N14—C141—C142—C143	52.5 (2)	N24—C241—C242—C243	53.9 (2)
C141—C142—C143—C144	−54.2 (2)	C241—C242—C243—C244	−53.8 (2)
C142—C143—C144—C145	56.0 (2)	C242—C243—C244—C245	54.1 (2)
C143—C144—C145—N14	−56.2 (2)	C243—C244—C245—N24	−55.5 (2)
N13—C14—N14—C141	177.79 (17)	N23—C24—N24—C241	−179.35 (16)
C15—C14—N14—C141	−3.8 (3)	C25—C24—N24—C241	−0.8 (3)
N13—C14—N14—C145	23.7 (2)	N23—C24—N24—C245	17.1 (2)
C15—C14—N14—C145	−157.90 (18)	C25—C24—N24—C245	−164.34 (17)
C142—C141—N14—C14	151.72 (17)	C242—C241—N24—C24	139.29 (18)
C142—C141—N14—C145	−52.7 (2)	C242—C241—N24—C245	−56.0 (2)
C144—C145—N14—C14	−149.19 (17)	C244—C245—N24—C24	−137.68 (18)
C144—C145—N14—C141	55.1 (2)	C244—C245—N24—C241	57.3 (2)
N13—C14—C15—C16	1.4 (3)	N23—C24—C25—C26	−1.4 (3)
N14—C14—C15—C16	−176.88 (17)	N24—C24—C25—C26	−179.93 (17)
C12—N11—C16—O16	−179.43 (15)	C22—N21—C26—O26	−178.93 (15)
C12—N11—C16—C15	0.5 (3)	C22—N21—C26—C25	1.0 (3)
C14—C15—C16—N11	−0.6 (3)	C24—C25—C26—N21	1.1 (3)
C14—C15—C16—O16	179.34 (16)	C24—C25—C26—O26	−178.90 (15)
C166—C161—C162—C163	−0.1 (3)	C266—C261—C262—C263	−0.5 (3)
C167—C161—C162—C163	178.70 (18)	C267—C261—C262—C263	−178.03 (18)
C161—C162—C163—C164	0.5 (3)	C261—C262—C263—C264	−0.1 (3)
C162—C163—C164—C165	−0.7 (3)	C262—C263—C264—C265	0.5 (3)
C162—C161—C167—O16	108.5 (2)	C263—C264—C265—C266	−0.2 (3)
C166—C161—C167—O16	−72.7 (2)	C262—C261—C266—C265	0.8 (3)
C163—C164—C165—C166	0.5 (3)	C267—C261—C266—C265	178.34 (18)
C164—C165—C166—C161	−0.1 (3)	C264—C265—C266—C261	−0.5 (3)
C162—C161—C166—C165	−0.1 (3)	C266—C261—C267—O26	110.7 (2)
C167—C161—C166—C165	−178.89 (19)	C262—C261—C267—O26	−71.9 (2)
N11—C16—O16—C167	−1.4 (2)	N21—C26—O26—C267	−2.6 (2)
C15—C16—O16—C167	178.57 (16)	C25—C26—O26—C267	177.40 (16)
C161—C167—O16—C16	167.65 (16)	C261—C267—O26—C26	169.90 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N12—H12A···N21	0.88	2.29	3.105 (2)	155
N12—H12B···N23^i	0.88	2.10	2.927 (2)	155
N22—H22A···N11^ii	0.88	2.27	3.064 (2)	149
N22—H22B···N13	0.88	2.10	2.920 (2)	154

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