Amino-substituted O⁶-benzyl-5-nitrosopyrimidines: interplay of molecular, molecular-electronic and supramolecular structures

The structures of eight 2,4,6-trisubstituted-5-nitrosopyrimidines (one of which crystallizes in two polymorphs) have been determined, including seven O⁶-benzyl derivatives which are potential, or proven, in vitro inhibitors of the human DNA-repair protein O⁶-alkylguanine-DNA-transferase. In the derivatives having an amino substituent at the 4-position, an intramolecular N—H...O hydrogen bond with the nitroso O as an acceptor leads to an overall molecular shape similar to that of substituted purines. There is a marked propensity for these nitroso compounds to crystallize with Z′ = 2. The structure of an analogue with no nitroso group is also reported for comparative purposes. Compounds containing the N-alkyl substituents —NHCH₂COOEt, —NHCH₂CH₂COOEt and —NHCH(CH₂Ph)COOEt, derived from amino acid esters, exhibit a rich variety of conformational behaviour, and in all of the nitroso compounds the bond lengths provide strong evidence for a highly polarized electronic structure. Associated with this polarization is extensive charge-assisted hydrogen bonding between the molecules, leading to supramolecular aggregation in the form of finite (zero-dimensional) aggregates, chains, molecular ladders, sheets and frameworks.

Computing details

For all compounds, data collection: Kappa-CCD server software (Nonius, 1997). Cell refinement: DENZO-SMN (Otwinowski & Minor, 1997) for (3), (5A), (5B), (7), (8), (9), (10), (11); DENZO (Otwinowski & Minor, 1997) for (4), (6). Data reduction: DENZO-SMN (Otwinowski & Minor, 1997) for (3), (5A), (5B), (7), (8), (9), (10), (11); DENZO (Otwinowski & Minor, 1997) for (4), (6). For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: PLATON (Spek, 2001). Software used to prepare material for publication: SHELXL97 (Sheldrick, 1997b) and PRPKAPPA (Ferguson, 1999) for (3), (4), (5A), (5B), (7), (8), (9), (10), (11); SHELXL97 SHELXL97 (Sheldrick, 1997b) and PRPKAPPA (Ferguson, 1999) for (6).

(3) 2-Amino-4-benzylamino-6-benzyloxy-5-nitrosopyrimidine

Crystal data

C18H17N5O2	F(000) = 1408
Mr = 335.37	Dx = 1.362 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.677 (2) Å	Cell parameters from 21450 reflections
b = 13.362 (3) Å	θ = 1.0–27.5°
c = 21.478 (4) Å	µ = 0.09 mm^−1
β = 102.58 (3)°	T = 150 K
V = 3270.7 (11) Å^3	Block, purple
Z = 8	0.34 × 0.18 × 0.18 mm

Data collection

Kappa-CCD diffractometer	7334 independent reflections
Radiation source: fine-focus sealed X-ray tube	4449 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.063
φ scans, and ω scans with κ offsets	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −14→14
Tmin = 0.969, Tmax = 0.983	k = −17→17
36834 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) = 0.150	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0833P)^2] where P = (Fo^2 + 2Fc^2)/3
7334 reflections	(Δ/σ)max = 0.001
451 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.41 e Å^−3

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

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

	x	y	z	Uiso*/Ueq
N11	0.72275 (12)	0.80433 (11)	0.25679 (7)	0.0225 (4)
C12	0.64409 (15)	0.76915 (14)	0.29038 (9)	0.0215 (4)
N12	0.62340 (13)	0.67198 (11)	0.28445 (8)	0.0268 (4)
N13	0.58763 (12)	0.82167 (11)	0.32740 (7)	0.0225 (4)
C14	0.61234 (15)	0.91950 (14)	0.33366 (9)	0.0209 (4)
C141	0.49667 (15)	0.88079 (14)	0.45839 (9)	0.0241 (4)
C142	0.40942 (17)	0.84741 (15)	0.48737 (10)	0.0300 (5)
C143	0.43522 (19)	0.79373 (15)	0.54365 (11)	0.0358 (5)
C144	0.5494 (2)	0.77246 (17)	0.57219 (11)	0.0401 (6)
C145	0.63678 (19)	0.80565 (17)	0.54421 (10)	0.0393 (6)
C146	0.61181 (17)	0.85974 (16)	0.48770 (10)	0.0322 (5)
C147	0.46236 (16)	0.93826 (15)	0.39689 (10)	0.0275 (5)
N14	0.55851 (13)	0.97465 (12)	0.36995 (8)	0.0250 (4)
C15	0.69525 (15)	0.96644 (13)	0.30181 (9)	0.0211 (4)
N15	0.72645 (13)	1.06334 (11)	0.30250 (8)	0.0261 (4)
O15	0.68109 (12)	1.12291 (10)	0.33691 (7)	0.0315 (3)
C16	0.74592 (15)	0.89990 (13)	0.26271 (9)	0.0205 (4)
C161	0.91781 (16)	0.94421 (14)	0.14578 (10)	0.0244 (4)
C162	0.85096 (17)	0.98018 (16)	0.08877 (11)	0.0351 (5)
C163	0.89713 (19)	1.04988 (18)	0.05312 (11)	0.0446 (6)
C164	1.00978 (19)	1.08450 (17)	0.07418 (12)	0.0414 (6)
C165	1.07737 (18)	1.04791 (16)	0.13024 (11)	0.0351 (5)
C166	1.03279 (16)	0.97820 (14)	0.16600 (10)	0.0273 (5)
C167	0.86425 (17)	0.87567 (14)	0.18617 (10)	0.0294 (5)
O16	0.82046 (11)	0.94060 (9)	0.23052 (6)	0.0256 (3)
N21	1.28017 (13)	0.83599 (11)	0.25079 (8)	0.0234 (4)
C22	1.35551 (15)	0.87739 (14)	0.21750 (9)	0.0217 (4)
N22	1.36975 (13)	0.97493 (11)	0.22494 (8)	0.0282 (4)
N23	1.41586 (12)	0.83015 (11)	0.17965 (8)	0.0229 (4)
C24	1.39762 (15)	0.73157 (14)	0.17216 (9)	0.0211 (4)
C241	1.52442 (16)	0.68368 (14)	0.03603 (9)	0.0249 (4)
C242	1.60612 (16)	0.61795 (14)	0.02028 (10)	0.0274 (5)
C243	1.58884 (17)	0.57701 (15)	−0.04033 (10)	0.0311 (5)
C244	1.49054 (18)	0.60106 (16)	−0.08612 (10)	0.0343 (5)
C246	1.42553 (17)	0.70853 (15)	−0.01085 (10)	0.0311 (5)
C245	1.40869 (18)	0.66696 (16)	−0.07109 (10)	0.0361 (5)
C247	1.53934 (17)	0.72553 (15)	0.10228 (10)	0.0287 (5)
N24	1.45421 (13)	0.68138 (12)	0.13498 (8)	0.0246 (4)
C25	1.31737 (15)	0.67867 (13)	0.20373 (9)	0.0219 (4)
N25	1.28927 (14)	0.58079 (11)	0.19968 (8)	0.0286 (4)
O25	1.33788 (13)	0.52564 (10)	0.16443 (7)	0.0377 (4)
C26	1.26368 (15)	0.74022 (14)	0.24356 (9)	0.0219 (4)
C261	1.08612 (16)	0.68076 (14)	0.35586 (10)	0.0260 (4)
C262	1.14663 (17)	0.63364 (16)	0.41034 (10)	0.0333 (5)
C263	1.09523 (18)	0.55771 (17)	0.43825 (10)	0.0380 (5)
C264	0.98147 (18)	0.53005 (16)	0.41231 (11)	0.0348 (5)
C265	0.91835 (17)	0.57870 (15)	0.35897 (10)	0.0286 (5)
C266	0.97098 (16)	0.65294 (14)	0.33053 (10)	0.0258 (4)
C267	1.14750 (17)	0.75406 (15)	0.32164 (10)	0.0319 (5)
O26	1.19289 (11)	0.69385 (9)	0.27542 (6)	0.0273 (3)
H12A	0.5773	0.6417	0.3061	0.032*
H12B	0.6578	0.6331	0.2626	0.032*
H142	0.3298	0.8616	0.4682	0.036*
H143	0.3735	0.7715	0.5627	0.043*
H144	0.5674	0.7353	0.6108	0.048*
H145	0.7162	0.7914	0.5638	0.047*
H146	0.6739	0.8823	0.4691	0.039*
H14A	0.4120	0.8947	0.3649	0.033*
H14B	0.4143	0.9964	0.4041	0.033*
H14	0.5823	1.0367	0.3782	0.030*
H162	0.7729	0.9569	0.0740	0.042*
H163	0.8507	1.0738	0.0140	0.053*
H164	1.0408	1.1333	0.0502	0.050*
H165	1.1557	1.0710	0.1444	0.042*
H166	1.0805	0.9533	0.2045	0.033*
H16A	0.7993	0.8369	0.1596	0.035*
H16B	0.9235	0.8284	0.2096	0.035*
H22A	1.4163	1.0032	0.2035	0.034*
H22B	1.3210	1.0108	0.2469	0.034*
H242	1.6745	0.6010	0.0514	0.033*
H243	1.6452	0.5320	−0.0504	0.037*
H244	1.4788	0.5728	−0.1276	0.041*
H246	1.3695	0.7543	−0.0013	0.037*
H245	1.3406	0.6836	−0.1025	0.043*
H24A	1.6198	0.7114	0.1268	0.034*
H24B	1.5287	0.7990	0.0999	0.034*
H24	1.4395	0.6170	0.1296	0.029*
H262	1.2247	0.6537	0.4289	0.040*
H263	1.1383	0.5248	0.4752	0.046*
H264	0.9461	0.4773	0.4311	0.042*
H265	0.8389	0.5610	0.3420	0.034*
H266	0.9281	0.6853	0.2933	0.031*
H26A	1.0921	0.8055	0.2997	0.038*
H26B	1.2123	0.7877	0.3518	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0246 (8)	0.0199 (9)	0.0236 (9)	0.0011 (6)	0.0062 (7)	0.0010 (7)
C12	0.0204 (10)	0.0223 (10)	0.0205 (11)	−0.0002 (7)	0.0020 (8)	0.0037 (8)
N12	0.0293 (9)	0.0199 (9)	0.0337 (11)	−0.0020 (7)	0.0124 (7)	0.0002 (8)
N13	0.0237 (8)	0.0224 (9)	0.0219 (9)	−0.0011 (6)	0.0057 (7)	0.0014 (7)
C14	0.0212 (10)	0.0235 (10)	0.0177 (10)	0.0001 (7)	0.0034 (7)	0.0011 (8)
C141	0.0267 (10)	0.0228 (10)	0.0251 (11)	−0.0009 (8)	0.0108 (8)	−0.0058 (9)
C142	0.0282 (11)	0.0298 (11)	0.0349 (13)	−0.0011 (8)	0.0135 (9)	−0.0046 (10)
C143	0.0455 (14)	0.0323 (12)	0.0359 (14)	−0.0062 (9)	0.0226 (11)	−0.0009 (10)
C144	0.0516 (15)	0.0419 (14)	0.0286 (13)	0.0004 (10)	0.0131 (11)	0.0057 (11)
C145	0.0361 (12)	0.0540 (15)	0.0264 (13)	0.0030 (10)	0.0042 (9)	0.0031 (11)
C146	0.0310 (12)	0.0426 (13)	0.0250 (12)	−0.0027 (9)	0.0101 (9)	−0.0013 (10)
C147	0.0243 (11)	0.0327 (12)	0.0281 (12)	0.0018 (8)	0.0112 (8)	−0.0010 (9)
N14	0.0312 (9)	0.0223 (9)	0.0237 (9)	−0.0022 (6)	0.0113 (7)	−0.0026 (7)
C15	0.0231 (10)	0.0210 (10)	0.0195 (10)	−0.0014 (7)	0.0052 (8)	0.0011 (8)
N15	0.0317 (9)	0.0232 (9)	0.0238 (10)	−0.0014 (7)	0.0074 (7)	−0.0027 (7)
O15	0.0429 (9)	0.0233 (8)	0.0324 (9)	−0.0013 (6)	0.0171 (7)	−0.0061 (6)
C16	0.0197 (9)	0.0225 (10)	0.0194 (10)	−0.0002 (7)	0.0047 (7)	0.0033 (8)
C161	0.0269 (10)	0.0210 (10)	0.0286 (12)	0.0011 (7)	0.0132 (8)	−0.0023 (9)
C162	0.0225 (11)	0.0478 (14)	0.0356 (13)	−0.0031 (9)	0.0078 (9)	0.0018 (11)
C163	0.0445 (14)	0.0569 (16)	0.0319 (14)	0.0022 (11)	0.0073 (10)	0.0148 (12)
C164	0.0471 (14)	0.0398 (14)	0.0425 (15)	−0.0035 (10)	0.0212 (11)	0.0103 (11)
C165	0.0302 (12)	0.0372 (13)	0.0413 (14)	−0.0074 (9)	0.0148 (10)	−0.0006 (11)
C166	0.0254 (10)	0.0298 (11)	0.0270 (12)	0.0013 (8)	0.0063 (8)	0.0002 (9)
C167	0.0340 (11)	0.0222 (11)	0.0379 (13)	−0.0001 (8)	0.0208 (9)	−0.0055 (9)
O16	0.0318 (8)	0.0224 (7)	0.0271 (8)	−0.0034 (5)	0.0162 (6)	−0.0018 (6)
N21	0.0263 (9)	0.0195 (9)	0.0256 (10)	−0.0002 (6)	0.0081 (7)	−0.0001 (7)
C22	0.0219 (10)	0.0214 (10)	0.0206 (11)	0.0005 (7)	0.0023 (7)	0.0002 (8)
N22	0.0353 (9)	0.0189 (9)	0.0349 (11)	−0.0014 (7)	0.0175 (8)	0.0019 (7)
N23	0.0258 (8)	0.0205 (9)	0.0229 (9)	−0.0002 (6)	0.0067 (7)	−0.0002 (7)
C24	0.0213 (10)	0.0240 (11)	0.0174 (10)	0.0016 (7)	0.0032 (7)	0.0006 (8)
C241	0.0261 (10)	0.0251 (11)	0.0258 (11)	−0.0072 (8)	0.0104 (8)	0.0013 (9)
C242	0.0238 (10)	0.0312 (11)	0.0287 (12)	−0.0029 (8)	0.0090 (8)	0.0010 (9)
C243	0.0320 (11)	0.0329 (12)	0.0328 (13)	−0.0046 (9)	0.0169 (9)	−0.0044 (10)
C244	0.0420 (13)	0.0394 (13)	0.0244 (12)	−0.0139 (10)	0.0137 (9)	−0.0036 (10)
C246	0.0277 (11)	0.0347 (12)	0.0330 (13)	0.0014 (8)	0.0110 (9)	0.0039 (10)
C245	0.0345 (12)	0.0450 (14)	0.0268 (12)	−0.0080 (10)	0.0025 (9)	0.0097 (11)
C247	0.0275 (11)	0.0318 (12)	0.0302 (12)	−0.0058 (8)	0.0137 (9)	−0.0038 (9)
N24	0.0280 (9)	0.0219 (9)	0.0267 (10)	−0.0025 (6)	0.0124 (7)	−0.0029 (7)
C25	0.0271 (10)	0.0190 (10)	0.0204 (11)	−0.0004 (7)	0.0071 (8)	−0.0012 (8)
N25	0.0381 (10)	0.0217 (9)	0.0291 (10)	0.0008 (7)	0.0143 (8)	−0.0036 (8)
O25	0.0547 (10)	0.0252 (8)	0.0411 (10)	−0.0014 (6)	0.0275 (8)	−0.0074 (7)
C26	0.0215 (10)	0.0214 (11)	0.0226 (11)	−0.0016 (7)	0.0045 (8)	0.0015 (8)
C261	0.0289 (11)	0.0259 (11)	0.0275 (12)	−0.0015 (8)	0.0152 (8)	−0.0071 (9)
C262	0.0238 (11)	0.0498 (14)	0.0274 (12)	−0.0024 (9)	0.0081 (9)	−0.0079 (10)
C263	0.0336 (12)	0.0560 (15)	0.0252 (12)	0.0073 (10)	0.0084 (9)	0.0081 (11)
C264	0.0401 (12)	0.0358 (13)	0.0333 (13)	−0.0006 (9)	0.0186 (10)	0.0040 (10)
C265	0.0252 (10)	0.0299 (11)	0.0314 (12)	−0.0018 (8)	0.0075 (8)	−0.0043 (9)
C266	0.0281 (10)	0.0263 (11)	0.0248 (11)	0.0033 (8)	0.0092 (8)	−0.0004 (9)
C267	0.0364 (12)	0.0277 (12)	0.0388 (14)	−0.0039 (9)	0.0240 (10)	−0.0101 (10)
O26	0.0345 (8)	0.0213 (7)	0.0314 (8)	−0.0041 (5)	0.0189 (6)	−0.0049 (6)

Geometric parameters (Å, º)

N11—C16	1.306 (2)	N21—C26	1.298 (2)
N11—C12	1.369 (2)	N21—C22	1.366 (2)
C12—N12	1.322 (2)	C22—N22	1.319 (2)
C12—N13	1.337 (2)	C22—N23	1.344 (2)
N12—H12A	0.88	N22—H22A	0.87
N12—H12B	0.86	N22—H22B	0.94
N13—C14	1.339 (2)	N23—C24	1.338 (2)
C14—N14	1.326 (2)	C24—N24	1.324 (2)
C14—C15	1.445 (2)	C24—C25	1.454 (2)
C141—C142	1.379 (3)	C241—C242	1.392 (3)
C141—C146	1.384 (3)	C241—C246	1.397 (3)
C141—C147	1.505 (3)	C241—C247	1.503 (3)
C142—C143	1.381 (3)	C242—C243	1.386 (3)
C142—H142	0.9500	C242—H242	0.9500
C143—C144	1.370 (3)	C243—C244	1.377 (3)
C143—H143	0.9500	C243—H243	0.9500
C144—C145	1.366 (3)	C244—C245	1.388 (3)
C144—H144	0.9500	C244—H244	0.9500
C145—C146	1.388 (3)	C246—C245	1.382 (3)
C145—H145	0.9500	C246—H246	0.9500
C146—H146	0.9500	C245—H245	0.9500
C147—N14	1.454 (2)	C247—N24	1.461 (2)
C147—H14A	0.9900	C247—H24A	0.9900
C147—H14B	0.9900	C247—H24B	0.9900
N14—H14	0.88	N24—H24	0.88
C15—N15	1.344 (2)	C25—N25	1.347 (2)
C15—C16	1.436 (3)	C25—C26	1.426 (2)
N15—O15	1.2772 (19)	N25—O25	1.275 (2)
C16—O16	1.339 (2)	C26—O26	1.335 (2)
C161—C162	1.387 (3)	C261—C262	1.380 (3)
C161—C166	1.394 (3)	C261—C266	1.387 (3)
C161—C167	1.490 (3)	C261—C267	1.498 (3)
C162—C163	1.387 (3)	C262—C263	1.380 (3)
C162—H162	0.9500	C262—H262	0.9500
C163—C164	1.375 (3)	C263—C264	1.375 (3)
C163—H163	0.9500	C263—H263	0.9500
C164—C165	1.378 (3)	C264—C265	1.382 (3)
C164—H164	0.9500	C264—H264	0.9500
C165—C166	1.379 (3)	C265—C266	1.378 (3)
C165—H165	0.9500	C265—H265	0.9500
C166—H166	0.9500	C266—H266	0.9500
C167—O16	1.461 (2)	C267—O26	1.464 (2)
C167—H16A	0.9900	C267—H26A	0.9900
C167—H16B	0.9900	C267—H26B	0.9900
C16—N11—C12	115.66 (15)	C26—N21—C22	115.61 (16)
N12—C12—N13	118.00 (16)	N22—C22—N23	117.94 (16)
N12—C12—N11	114.59 (16)	N22—C22—N21	114.54 (16)
N13—C12—N11	127.41 (17)	N23—C22—N21	127.51 (17)
C12—N12—H12A	121.3	C22—N22—H22A	116.2
C12—N12—H12B	123.5	C22—N22—H22B	119.2
H12A—N12—H12B	115.0	H22A—N22—H22B	123.8
C12—N13—C14	116.67 (15)	C24—N23—C22	116.39 (15)
N14—C14—N13	118.82 (16)	N24—C24—N23	118.92 (16)
N14—C14—C15	119.29 (17)	N24—C24—C25	119.46 (16)
N13—C14—C15	121.88 (16)	N23—C24—C25	121.61 (16)
C142—C141—C146	117.99 (19)	C242—C241—C246	118.54 (19)
C142—C141—C147	118.67 (17)	C242—C241—C247	121.38 (18)
C146—C141—C147	123.35 (17)	C246—C241—C247	120.07 (18)
C141—C142—C143	121.42 (19)	C243—C242—C241	120.68 (19)
C141—C142—H142	119.3	C243—C242—H242	119.7
C143—C142—H142	119.3	C241—C242—H242	119.7
C144—C143—C142	120.32 (19)	C244—C243—C242	120.46 (19)
C144—C143—H143	119.8	C244—C243—H243	119.8
C142—C143—H143	119.8	C242—C243—H243	119.8
C145—C144—C143	118.9 (2)	C243—C244—C245	119.4 (2)
C145—C144—H144	120.6	C243—C244—H244	120.3
C143—C144—H144	120.6	C245—C244—H244	120.3
C144—C145—C146	121.3 (2)	C245—C246—C241	120.40 (19)
C144—C145—H145	119.4	C245—C246—H246	119.8
C146—C145—H145	119.4	C241—C246—H246	119.8
C141—C146—C145	120.13 (19)	C246—C245—C244	120.5 (2)
C141—C146—H146	119.9	C246—C245—H245	119.7
C145—C146—H146	119.9	C244—C245—H245	119.7
N14—C147—C141	116.03 (15)	N24—C247—C241	110.75 (15)
N14—C147—H14A	108.3	N24—C247—H24A	109.5
C141—C147—H14A	108.3	C241—C247—H24A	109.5
N14—C147—H14B	108.3	N24—C247—H24B	109.5
C141—C147—H14B	108.3	C241—C247—H24B	109.5
H14A—C147—H14B	107.4	H24A—C247—H24B	108.1
C14—N14—C147	123.62 (16)	C24—N24—C247	124.51 (16)
C14—N14—H14	118.2	C24—N24—H24	117.7
C147—N14—H14	118.2	C247—N24—H24	117.7
N15—C15—C16	117.23 (16)	N25—C25—C26	117.78 (16)
N15—C15—C14	128.39 (17)	N25—C25—C24	127.93 (16)
C16—C15—C14	114.33 (16)	C26—C25—C24	114.30 (16)
O15—N15—C15	117.46 (15)	O25—N25—C25	117.78 (15)
N11—C16—O16	119.41 (16)	N21—C26—O26	119.23 (16)
N11—C16—C15	124.02 (16)	N21—C26—C25	124.54 (16)
O16—C16—C15	116.57 (16)	O26—C26—C25	116.23 (16)
C162—C161—C166	118.75 (18)	C262—C261—C266	118.94 (18)
C162—C161—C167	120.02 (18)	C262—C261—C267	120.21 (18)
C166—C161—C167	121.12 (19)	C266—C261—C267	120.63 (19)
C161—C162—C163	120.55 (19)	C261—C262—C263	120.84 (19)
C161—C162—H162	119.7	C261—C262—H262	119.6
C163—C162—H162	119.7	C263—C262—H262	119.6
C164—C163—C162	120.2 (2)	C264—C263—C262	119.7 (2)
C164—C163—H163	119.9	C264—C263—H263	120.2
C162—C163—H163	119.9	C262—C263—H263	120.2
C163—C164—C165	119.5 (2)	C263—C264—C265	120.2 (2)
C163—C164—H164	120.2	C263—C264—H264	119.9
C165—C164—H164	120.2	C265—C264—H264	119.9
C164—C165—C166	120.8 (2)	C266—C265—C264	119.82 (19)
C164—C165—H165	119.6	C266—C265—H265	120.1
C166—C165—H165	119.6	C264—C265—H265	120.1
C165—C166—C161	120.1 (2)	C265—C266—C261	120.46 (19)
C165—C166—H166	120.0	C265—C266—H266	119.8
C161—C166—H166	120.0	C261—C266—H266	119.8
O16—C167—C161	105.41 (14)	O26—C267—C261	104.84 (15)
O16—C167—H16A	110.7	O26—C267—H26A	110.8
C161—C167—H16A	110.7	C261—C267—H26A	110.8
O16—C167—H16B	110.7	O26—C267—H26B	110.8
C161—C167—H16B	110.7	C261—C267—H26B	110.8
H16A—C167—H16B	108.8	H26A—C267—H26B	108.9
C16—O16—C167	117.04 (14)	C26—O26—C267	116.66 (14)
C16—N11—C12—N12	−179.00 (16)	C26—N21—C22—N22	179.18 (16)
C16—N11—C12—N13	1.1 (3)	C26—N21—C22—N23	−1.6 (3)
N12—C12—N13—C14	178.53 (16)	N22—C22—N23—C24	−178.73 (16)
N11—C12—N13—C14	−1.6 (3)	N21—C22—N23—C24	2.1 (3)
C12—N13—C14—N14	−179.96 (16)	C22—N23—C24—N24	179.52 (16)
C12—N13—C14—C15	0.4 (2)	C22—N23—C24—C25	−0.4 (3)
C146—C141—C142—C143	−0.6 (3)	C246—C241—C242—C243	−0.9 (3)
C147—C141—C142—C143	179.59 (19)	C247—C241—C242—C243	177.49 (17)
C141—C142—C143—C144	0.1 (3)	C241—C242—C243—C244	0.2 (3)
C142—C143—C144—C145	0.3 (3)	C242—C243—C244—C245	0.1 (3)
C143—C144—C145—C146	−0.3 (3)	C242—C241—C246—C245	1.2 (3)
C142—C141—C146—C145	0.6 (3)	C247—C241—C246—C245	−177.20 (18)
C147—C141—C146—C145	−179.5 (2)	C241—C246—C245—C244	−0.9 (3)
C144—C145—C146—C141	−0.2 (3)	C243—C244—C245—C246	0.2 (3)
C142—C141—C147—N14	177.77 (17)	C242—C241—C247—N24	−108.39 (19)
C146—C141—C147—N14	−2.1 (3)	C246—C241—C247—N24	70.0 (2)
N13—C14—N14—C147	−8.4 (3)	N23—C24—N24—C247	1.9 (3)
C15—C14—N14—C147	171.22 (17)	C25—C24—N24—C247	−178.15 (17)
C141—C147—N14—C14	83.8 (2)	C241—C247—N24—C24	−139.77 (18)
N14—C14—C15—N15	−1.3 (3)	N24—C24—C25—N25	−1.2 (3)
N13—C14—C15—N15	178.33 (18)	N23—C24—C25—N25	178.77 (18)
N14—C14—C15—C16	−178.62 (16)	N24—C24—C25—C26	178.69 (16)
N13—C14—C15—C16	1.0 (3)	N23—C24—C25—C26	−1.4 (3)
C16—C15—N15—O15	179.60 (16)	C26—C25—N25—O25	−179.52 (17)
C14—C15—N15—O15	2.4 (3)	C24—C25—N25—O25	0.3 (3)
C12—N11—C16—O16	−178.85 (15)	C22—N21—C26—O26	178.79 (16)
C12—N11—C16—C15	0.6 (3)	C22—N21—C26—C25	−0.6 (3)
N15—C15—C16—N11	−179.18 (17)	N25—C25—C26—N21	−178.21 (18)
C14—C15—C16—N11	−1.6 (3)	C24—C25—C26—N21	1.9 (3)
N15—C15—C16—O16	0.3 (2)	N25—C25—C26—O26	2.4 (2)
C14—C15—C16—O16	177.88 (15)	C24—C25—C26—O26	−177.45 (16)
C166—C161—C162—C163	−1.0 (3)	C266—C261—C262—C263	2.1 (3)
C167—C161—C162—C163	175.11 (19)	C267—C261—C262—C263	−172.52 (18)
C161—C162—C163—C164	−0.3 (3)	C261—C262—C263—C264	−1.4 (3)
C162—C163—C164—C165	1.4 (4)	C262—C263—C264—C265	−0.7 (3)
C163—C164—C165—C166	−1.1 (3)	C263—C264—C265—C266	2.1 (3)
C164—C165—C166—C161	−0.3 (3)	C264—C265—C266—C261	−1.4 (3)
C162—C161—C166—C165	1.4 (3)	C262—C261—C266—C265	−0.7 (3)
C167—C161—C166—C165	−174.74 (18)	C267—C261—C266—C265	173.92 (17)
C162—C161—C167—O16	−91.9 (2)	C262—C261—C267—O26	90.1 (2)
C166—C161—C167—O16	84.2 (2)	C266—C261—C267—O26	−84.4 (2)
N11—C16—O16—C167	4.9 (2)	N21—C26—O26—C267	−5.9 (3)
C15—C16—O16—C167	−174.58 (16)	C25—C26—O26—C267	173.54 (16)
C161—C167—O16—C16	165.71 (15)	C261—C267—O26—C26	−172.39 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N14—H14···O15	0.88	1.97	2.630 (2)	131
N24—H24···O25	0.88	1.96	2.636 (2)	133
N12—H12B···N15^i	0.86	2.34	3.177 (2)	166
N22—H22B···N25^ii	0.94	2.12	3.063 (2)	175

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) −x+5/2, y+1/2, −z+1/2.

(4) Ethyl N-(2-amino-6-benzyloxypyrimidin-4-yl)gylcinate

Crystal data

C15H17N5O4	Z = 2
Mr = 331.34	F(000) = 348
Triclinic, P1	Dx = 1.411 Mg m^−3
a = 7.3525 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.5420 (5) Å	Cell parameters from 11231 reflections
c = 14.9454 (13) Å	θ = 1.0–27.5°
α = 91.797 (3)°	µ = 0.11 mm^−1
β = 100.467 (3)°	T = 150 K
γ = 106.102 (6)°	Needle, violet
V = 780.06 (10) Å^3	0.50 × 0.20 × 0.10 mm

Data collection

Kappa-CCD diffractometer	3418 independent reflections
Radiation source: fine-focus sealed X-ray tube	1860 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
φ scans, and ω scans with κ offsets	θmax = 27.5°, θmin = 1.4°
Absorption correction: multi-scan Sortav (Blessing, 1995 & 1997)	h = −9→9
Tmin = 0.949, Tmax = 0.990	k = −9→9
10165 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.164	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0778P)^2] where P = (Fo^2 + 2Fc^2)/3
3418 reflections	(Δ/σ)max < 0.001
218 parameters	Δρmax = 0.39 e Å^−3
0 restraints	Δρmin = −0.51 e Å^−3

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

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

	x	y	z	Uiso*/Ueq
N1	0.4868 (3)	0.8017 (3)	0.42584 (13)	0.0264 (5)
C2	0.6363 (3)	0.7661 (3)	0.48421 (16)	0.0255 (5)
N2	0.7993 (3)	0.7959 (3)	0.45505 (14)	0.0331 (5)
N3	0.6330 (3)	0.7038 (3)	0.56703 (13)	0.0265 (5)
C4	0.4658 (3)	0.6690 (3)	0.59524 (16)	0.0245 (5)
N4	0.4573 (3)	0.6023 (3)	0.67613 (13)	0.0288 (5)
C5	0.2981 (3)	0.7031 (3)	0.54129 (16)	0.0239 (5)
N5	0.1237 (3)	0.6805 (3)	0.56383 (13)	0.0288 (5)
O5	0.0994 (2)	0.6172 (2)	0.64024 (11)	0.0347 (5)
C6	0.3243 (3)	0.7695 (3)	0.45470 (16)	0.0239 (5)
O6	0.1708 (2)	0.7983 (2)	0.40071 (10)	0.0271 (4)
C67	0.1965 (3)	0.8561 (3)	0.31110 (16)	0.0288 (6)
C61	0.0016 (3)	0.8490 (3)	0.25717 (16)	0.0286 (6)
C62	−0.0762 (4)	0.9941 (4)	0.26918 (18)	0.0362 (6)
C63	−0.2574 (4)	0.9871 (4)	0.2210 (2)	0.0489 (8)
C64	−0.3588 (4)	0.8399 (5)	0.1593 (2)	0.0573 (9)
C65	−0.2833 (4)	0.6944 (5)	0.1459 (2)	0.0528 (8)
C66	−0.1029 (4)	0.6981 (4)	0.19537 (18)	0.0389 (7)
C7	0.6207 (3)	0.5638 (3)	0.73296 (16)	0.0298 (6)
O81	0.6461 (3)	0.8241 (3)	0.83713 (13)	0.0445 (5)
C8	0.7069 (3)	0.7010 (4)	0.81541 (16)	0.0307 (6)
O82	0.8650 (2)	0.6655 (2)	0.86189 (11)	0.0368 (5)
C9	0.9701 (4)	0.7979 (4)	0.93927 (18)	0.0440 (7)
C10	1.1550 (4)	0.7549 (5)	0.9771 (2)	0.0610 (9)
H2A	0.9004	0.7751	0.4895	0.040*
H2B	0.8074	0.8369	0.4010	0.040*
H4	0.3480	0.5807	0.6958	0.035*
H67A	0.2531	0.7723	0.2804	0.035*
H67B	0.2845	0.9836	0.3166	0.035*
H62	−0.0045	1.0984	0.3107	0.043*
H63	−0.3117	1.0849	0.2308	0.059*
H64	−0.4821	0.8373	0.1252	0.069*
H65	−0.3547	0.5923	0.1030	0.063*
H66	−0.0512	0.5978	0.1870	0.047*
H7A	0.7208	0.5663	0.6964	0.036*
H7B	0.5792	0.4378	0.7533	0.036*
H9A	0.8910	0.7900	0.9868	0.053*
H9B	0.9984	0.9252	0.9197	0.053*
H10A	1.1258	0.6307	0.9987	0.091*
H10B	1.2292	0.8461	1.0282	0.091*
H10C	1.2310	0.7598	0.9293	0.091*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0205 (10)	0.0291 (12)	0.0306 (12)	0.0094 (8)	0.0044 (8)	0.0010 (9)
C2	0.0212 (13)	0.0249 (14)	0.0305 (14)	0.0079 (10)	0.0041 (10)	−0.0018 (11)
N2	0.0223 (11)	0.0458 (14)	0.0324 (13)	0.0112 (9)	0.0057 (9)	0.0064 (10)
N3	0.0200 (10)	0.0296 (12)	0.0302 (12)	0.0092 (8)	0.0027 (8)	0.0011 (9)
C4	0.0247 (13)	0.0223 (13)	0.0260 (14)	0.0083 (10)	0.0020 (10)	−0.0035 (10)
N4	0.0258 (11)	0.0352 (13)	0.0265 (12)	0.0112 (9)	0.0035 (8)	0.0049 (10)
C5	0.0196 (12)	0.0245 (13)	0.0283 (14)	0.0088 (9)	0.0034 (9)	−0.0009 (10)
N5	0.0272 (12)	0.0318 (12)	0.0278 (12)	0.0090 (9)	0.0062 (9)	0.0019 (9)
O5	0.0315 (10)	0.0448 (11)	0.0320 (11)	0.0141 (8)	0.0111 (7)	0.0094 (9)
C6	0.0209 (13)	0.0225 (13)	0.0285 (14)	0.0093 (9)	0.0010 (10)	−0.0021 (10)
O6	0.0227 (9)	0.0349 (10)	0.0269 (10)	0.0126 (7)	0.0051 (7)	0.0075 (7)
C67	0.0271 (13)	0.0352 (15)	0.0261 (14)	0.0122 (11)	0.0055 (10)	0.0052 (11)
C61	0.0278 (13)	0.0328 (15)	0.0277 (14)	0.0106 (11)	0.0077 (10)	0.0098 (12)
C62	0.0354 (15)	0.0406 (16)	0.0375 (16)	0.0152 (12)	0.0112 (12)	0.0110 (13)
C63	0.0393 (17)	0.061 (2)	0.057 (2)	0.0264 (15)	0.0138 (15)	0.0282 (17)
C64	0.0314 (16)	0.087 (3)	0.052 (2)	0.0167 (17)	0.0020 (14)	0.031 (2)
C65	0.0394 (17)	0.066 (2)	0.0369 (18)	−0.0061 (15)	−0.0007 (13)	0.0014 (15)
C66	0.0366 (15)	0.0425 (17)	0.0333 (16)	0.0047 (12)	0.0061 (12)	0.0037 (13)
C7	0.0315 (14)	0.0318 (15)	0.0266 (14)	0.0124 (11)	0.0018 (10)	0.0032 (11)
O81	0.0480 (12)	0.0451 (12)	0.0425 (12)	0.0233 (10)	0.0005 (9)	−0.0075 (9)
C8	0.0318 (14)	0.0338 (16)	0.0272 (14)	0.0102 (11)	0.0053 (11)	0.0088 (12)
O82	0.0376 (10)	0.0370 (11)	0.0317 (10)	0.0123 (8)	−0.0055 (8)	0.0002 (8)
C9	0.0481 (17)	0.0422 (18)	0.0316 (16)	0.0062 (13)	−0.0062 (13)	−0.0029 (13)
C10	0.0484 (19)	0.060 (2)	0.060 (2)	0.0103 (15)	−0.0169 (15)	0.0090 (17)

Geometric parameters (Å, º)

N1—C6	1.306 (3)	C62—C63	1.381 (4)
N1—C2	1.368 (3)	C62—H62	0.9500
C2—N2	1.312 (3)	C63—C64	1.366 (4)
C2—N3	1.339 (3)	C63—H63	0.9500
N2—H2A	0.88	C64—C65	1.385 (5)
N2—H2B	0.88	C64—H64	0.9500
N3—C4	1.332 (3)	C65—C66	1.388 (4)
C4—N4	1.329 (3)	C65—H65	0.9500
C4—C5	1.436 (3)	C66—H66	0.9500
N4—C7	1.445 (3)	C7—C8	1.504 (3)
N4—H4	0.88	C7—H7A	0.9900
C5—N5	1.352 (3)	C7—H7B	0.9900
C5—C6	1.428 (3)	O81—C8	1.196 (3)
N5—O5	1.275 (2)	C8—O82	1.341 (3)
C6—O6	1.337 (3)	O82—C9	1.451 (3)
O6—C67	1.450 (3)	C9—C10	1.500 (4)
C67—C61	1.498 (3)	C9—H9A	0.9900
C67—H67A	0.9900	C9—H9B	0.9900
C67—H67B	0.9900	C10—H10A	0.9800
C61—C62	1.388 (3)	C10—H10B	0.9800
C61—C66	1.389 (4)	C10—H10C	0.9800
C6—N1—C2	115.6 (2)	C64—C63—C62	120.1 (3)
N2—C2—N3	117.2 (2)	C64—C63—H63	119.9
N2—C2—N1	115.9 (2)	C62—C63—H63	119.9
N3—C2—N1	126.9 (2)	C63—C64—C65	120.5 (3)
C2—N2—H2A	120.0	C63—C64—H64	119.8
C2—N2—H2B	120.0	C65—C64—H64	119.8
H2A—N2—H2B	120.0	C64—C65—C66	119.9 (3)
C4—N3—C2	116.93 (19)	C64—C65—H65	120.1
N4—C4—N3	118.1 (2)	C66—C65—H65	120.1
N4—C4—C5	120.0 (2)	C65—C66—C61	119.7 (3)
N3—C4—C5	121.9 (2)	C65—C66—H66	120.2
C4—N4—C7	122.43 (19)	C61—C66—H66	120.2
C4—N4—H4	118.8	N4—C7—C8	112.5 (2)
C7—N4—H4	118.8	N4—C7—H7A	109.1
N5—C5—C6	118.0 (2)	C8—C7—H7A	109.1
N5—C5—C4	127.4 (2)	N4—C7—H7B	109.1
C6—C5—C4	114.59 (19)	C8—C7—H7B	109.1
O5—N5—C5	117.87 (19)	H7A—C7—H7B	107.8
N1—C6—O6	119.0 (2)	O81—C8—O82	124.4 (2)
N1—C6—C5	124.0 (2)	O81—C8—C7	126.0 (2)
O6—C6—C5	116.94 (19)	O82—C8—C7	109.6 (2)
C6—O6—C67	116.35 (17)	C8—O82—C9	114.8 (2)
O6—C67—C61	107.39 (18)	O82—C9—C10	108.8 (2)
O6—C67—H67A	110.2	O82—C9—H9A	109.9
C61—C67—H67A	110.2	C10—C9—H9A	109.9
O6—C67—H67B	110.2	O82—C9—H9B	109.9
C61—C67—H67B	110.2	C10—C9—H9B	109.9
H67A—C67—H67B	108.5	H9A—C9—H9B	108.3
C62—C61—C66	119.6 (2)	C9—C10—H10A	109.5
C62—C61—C67	119.8 (2)	C9—C10—H10B	109.5
C66—C61—C67	120.6 (2)	H10A—C10—H10B	109.5
C63—C62—C61	120.2 (3)	C9—C10—H10C	109.5
C63—C62—H62	119.9	H10A—C10—H10C	109.5
C61—C62—H62	119.9	H10B—C10—H10C	109.5
C6—N1—C2—N2	179.2 (2)	N1—C6—O6—C67	2.7 (3)
C6—N1—C2—N3	−0.6 (3)	C5—C6—O6—C67	−176.80 (19)
N2—C2—N3—C4	−178.3 (2)	C6—O6—C67—C61	170.59 (19)
N1—C2—N3—C4	1.5 (4)	O6—C67—C61—C62	81.0 (3)
C2—N3—C4—N4	178.2 (2)	O6—C67—C61—C66	−98.7 (3)
C2—N3—C4—C5	−2.3 (3)	C66—C61—C62—C63	1.0 (4)
N3—C4—N4—C7	−1.1 (3)	C67—C61—C62—C63	−178.8 (2)
C5—C4—N4—C7	179.5 (2)	C61—C62—C63—C64	−1.9 (4)
N4—C4—C5—N5	2.3 (4)	C62—C63—C64—C65	1.5 (4)
N3—C4—C5—N5	−177.2 (2)	C63—C64—C65—C66	−0.2 (4)
N4—C4—C5—C6	−178.2 (2)	C64—C65—C66—C61	−0.8 (4)
N3—C4—C5—C6	2.3 (3)	C62—C61—C66—C65	0.4 (4)
C6—C5—N5—O5	178.4 (2)	C67—C61—C66—C65	−179.9 (2)
C4—C5—N5—O5	−2.1 (3)	C4—N4—C7—C8	108.0 (2)
C2—N1—C6—O6	−178.95 (19)	N4—C7—C8—O81	3.9 (4)
C2—N1—C6—C5	0.5 (3)	N4—C7—C8—O82	−175.88 (19)
N5—C5—C6—N1	178.2 (2)	O81—C8—O82—C9	−4.4 (4)
C4—C5—C6—N1	−1.4 (3)	C7—C8—O82—C9	175.4 (2)
N5—C5—C6—O6	−2.3 (3)	C8—O82—C9—C10	−172.9 (2)
C4—C5—C6—O6	178.12 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O5	0.88	1.96	2.623 (2)	131
N2—H2A···N5^i	0.88	2.12	2.987 (2)	171

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

(5A) Ethyl N-(2-amino-6 benzyloxy-5-nitrosopyrimidin-4-yl)-β-alaninate

Crystal data

C16H19N5O4	F(000) = 728
Mr = 345.36	Dx = 1.458 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.2399 (16) Å	Cell parameters from 66201 reflections
b = 31.1630 (14) Å	θ = 1.0–27.5°
c = 9.792 (4) Å	µ = 0.11 mm^−1
β = 100.200 (12)°	T = 150 K
V = 1573.7 (8) Å^3	Plate, blue
Z = 4	0.20 × 0.10 × 0.02 mm

Data collection

Kappa-CCD diffractometer	2525 independent reflections
Radiation source: fine-focus sealed X-ray tube	822 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
φ scans, and ω scans with κ offsets	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −6→6
Tmin = 0.979, Tmax = 0.998	k = −36→37
10470 measured reflections	l = −11→11

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)] = 0.106	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.283	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0757P)^2 + 2.3684P] where P = (Fo^2 + 2Fc^2)/3
2525 reflections	(Δ/σ)max = 0.002
227 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

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

	x	y	z	Uiso*/Ueq
N1	0.9265 (14)	0.4168 (2)	0.2453 (7)	0.053 (2)
C2	0.9267 (19)	0.4508 (3)	0.3336 (8)	0.058 (3)
N2	1.1277 (13)	0.4505 (2)	0.4369 (7)	0.059 (2)
N3	0.7538 (14)	0.4831 (2)	0.3308 (7)	0.051 (2)
C4	0.5553 (18)	0.4809 (3)	0.2231 (9)	0.052 (3)
N4	0.3830 (15)	0.5117 (2)	0.2111 (7)	0.057 (2)
C5	0.5266 (18)	0.4463 (3)	0.1260 (9)	0.050 (3)
N5	0.3306 (15)	0.4405 (3)	0.0150 (7)	0.062 (2)
O5	0.1513 (13)	0.4682 (2)	−0.0022 (6)	0.073 (2)
C6	0.7264 (19)	0.4166 (3)	0.1428 (9)	0.056 (3)
O6	0.7049 (12)	0.3841 (2)	0.0510 (6)	0.065 (2)
C67	0.9058 (17)	0.3523 (3)	0.0611 (9)	0.060 (3)
C61	0.823 (2)	0.3201 (3)	−0.0537 (9)	0.061 (3)
C62	0.595 (2)	0.3242 (3)	−0.1459 (8)	0.063 (3)
C63	0.540 (2)	0.2940 (3)	−0.2488 (10)	0.067 (3)
C64	0.705 (2)	0.2605 (3)	−0.2633 (10)	0.069 (3)
C65	0.927 (2)	0.2566 (3)	−0.1678 (10)	0.071 (3)
C66	0.990 (2)	0.2868 (3)	−0.0653 (10)	0.070 (3)
C7	0.3879 (16)	0.5479 (3)	0.3068 (8)	0.058 (3)
C8	0.1487 (16)	0.5752 (3)	0.2668 (8)	0.057 (3)
C9	0.1156 (19)	0.6117 (3)	0.3632 (9)	0.050 (3)
O91	−0.0761 (14)	0.6330 (2)	0.3515 (6)	0.073 (2)
O92	0.3289 (12)	0.61788 (18)	0.4604 (6)	0.0586 (19)
C10	0.3154 (18)	0.6550 (3)	0.5500 (9)	0.063 (3)
C11	0.5731 (17)	0.6589 (3)	0.6409 (9)	0.073 (3)
H2A	1.1446	0.4708	0.5004	0.071*
H2B	1.2442	0.4299	0.4421	0.071*
H4	0.2543	0.5106	0.1400	0.069*
H67A	0.9292	0.3379	0.1526	0.072*
H67B	1.0721	0.3658	0.0504	0.072*
H62	0.4791	0.3472	−0.1389	0.075*
H63	0.3810	0.2962	−0.3126	0.080*
H64	0.6649	0.2407	−0.3378	0.083*
H65	1.0384	0.2327	−0.1722	0.085*
H66	1.1501	0.2847	−0.0023	0.084*
H7A	0.5443	0.5655	0.3048	0.070*
H7B	0.3963	0.5370	0.4025	0.070*
H8A	0.1504	0.5873	0.1734	0.068*
H8B	−0.0051	0.5563	0.2593	0.068*
H10A	0.1784	0.6508	0.6065	0.075*
H10B	0.2754	0.6813	0.4935	0.075*
H11A	0.6083	0.6329	0.6977	0.110*
H11B	0.5739	0.6839	0.7014	0.110*
H11C	0.7072	0.6623	0.5835	0.110*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.049 (5)	0.073 (5)	0.034 (4)	−0.004 (4)	0.001 (4)	−0.002 (4)
C2	0.070 (8)	0.071 (8)	0.030 (5)	−0.005 (6)	−0.002 (6)	−0.005 (5)
N2	0.052 (5)	0.071 (5)	0.051 (5)	0.005 (4)	−0.001 (4)	−0.008 (4)
N3	0.040 (5)	0.072 (6)	0.040 (4)	0.000 (4)	0.000 (4)	0.000 (4)
C4	0.048 (7)	0.062 (7)	0.045 (6)	−0.001 (5)	0.010 (5)	−0.002 (5)
N4	0.060 (6)	0.067 (5)	0.041 (5)	−0.001 (5)	−0.005 (4)	−0.010 (4)
C5	0.048 (7)	0.059 (6)	0.044 (6)	−0.006 (5)	0.008 (5)	−0.004 (5)
N5	0.053 (5)	0.081 (6)	0.049 (5)	−0.003 (5)	0.003 (5)	−0.003 (4)
O5	0.065 (5)	0.087 (5)	0.059 (4)	0.019 (4)	−0.012 (4)	−0.015 (4)
C6	0.053 (7)	0.071 (7)	0.046 (6)	0.000 (6)	0.014 (6)	−0.003 (6)
O6	0.067 (5)	0.081 (5)	0.046 (4)	0.005 (4)	0.002 (3)	−0.009 (4)
C67	0.046 (6)	0.072 (7)	0.063 (7)	0.025 (6)	0.010 (5)	0.011 (6)
C61	0.085 (9)	0.055 (6)	0.042 (6)	−0.001 (6)	0.010 (6)	−0.009 (5)
C62	0.078 (9)	0.071 (7)	0.036 (5)	−0.001 (6)	0.001 (6)	−0.005 (5)
C63	0.067 (8)	0.080 (7)	0.054 (7)	−0.013 (7)	0.013 (6)	−0.006 (6)
C64	0.088 (9)	0.073 (8)	0.048 (6)	−0.006 (7)	0.017 (6)	−0.012 (5)
C65	0.077 (9)	0.066 (7)	0.072 (7)	−0.001 (6)	0.017 (7)	−0.008 (6)
C66	0.080 (9)	0.069 (7)	0.061 (7)	0.011 (7)	0.008 (6)	0.010 (6)
C7	0.045 (6)	0.095 (8)	0.032 (5)	0.004 (6)	−0.001 (5)	−0.002 (5)
C8	0.047 (7)	0.076 (7)	0.041 (5)	−0.001 (5)	−0.010 (5)	−0.009 (5)
C9	0.034 (6)	0.068 (7)	0.048 (6)	−0.007 (5)	0.009 (5)	0.014 (5)
O91	0.063 (5)	0.094 (5)	0.060 (4)	0.012 (4)	0.002 (4)	−0.006 (4)
O92	0.051 (5)	0.070 (4)	0.050 (4)	−0.002 (3)	−0.004 (3)	−0.007 (3)
C10	0.078 (8)	0.052 (6)	0.057 (6)	0.000 (5)	0.010 (6)	−0.007 (5)
C11	0.057 (8)	0.087 (8)	0.070 (7)	0.004 (6)	−0.002 (6)	−0.016 (5)

Geometric parameters (Å, º)

N1—C6	1.317 (10)	C63—C64	1.379 (12)
N1—C2	1.368 (10)	C63—H63	0.9500
C2—N2	1.325 (9)	C64—C65	1.363 (11)
C2—N3	1.351 (11)	C64—H64	0.9500
N2—H2A	0.88	C65—C66	1.374 (11)
N2—H2B	0.88	C65—H65	0.9500
N3—C4	1.345 (9)	C66—H66	0.9500
C4—N4	1.310 (10)	C7—C8	1.508 (10)
C4—C5	1.427 (11)	C7—H7A	0.9900
N4—C7	1.464 (9)	C7—H7B	0.9900
N4—H4	0.88	C8—C9	1.507 (12)
C5—N5	1.369 (9)	C8—H8A	0.9900
C5—C6	1.386 (12)	C8—H8B	0.9900
N5—O5	1.264 (9)	C9—O91	1.193 (10)
C6—O6	1.346 (9)	C9—O92	1.348 (9)
O6—C67	1.436 (9)	O92—C10	1.461 (9)
C67—C61	1.510 (11)	C10—C11	1.485 (10)
C67—H67A	0.9900	C10—H10A	0.9900
C67—H67B	0.9900	C10—H10B	0.9900
C61—C62	1.369 (11)	C11—H11A	0.9800
C61—C66	1.378 (12)	C11—H11B	0.9800
C62—C63	1.372 (11)	C11—H11C	0.9800
C62—H62	0.9500
C6—N1—C2	113.4 (8)	C65—C64—C63	118.3 (9)
N2—C2—N3	117.5 (8)	C65—C64—H64	120.9
N2—C2—N1	112.8 (9)	C63—C64—H64	120.9
N3—C2—N1	129.7 (8)	C64—C65—C66	120.4 (10)
C2—N2—H2A	120.0	C64—C65—H65	119.8
C2—N2—H2B	120.0	C66—C65—H65	119.8
H2A—N2—H2B	120.0	C65—C66—C61	120.1 (9)
C4—N3—C2	113.6 (8)	C65—C66—H66	119.9
N4—C4—N3	117.2 (8)	C61—C66—H66	119.9
N4—C4—C5	120.3 (8)	N4—C7—C8	110.4 (6)
N3—C4—C5	122.5 (9)	N4—C7—H7A	109.6
C4—N4—C7	125.0 (7)	C8—C7—H7A	109.6
C4—N4—H4	117.5	N4—C7—H7B	109.6
C7—N4—H4	117.5	C8—C7—H7B	109.6
N5—C5—C6	116.8 (9)	H7A—C7—H7B	108.1
N5—C5—C4	127.2 (9)	C9—C8—C7	116.4 (7)
C6—C5—C4	115.9 (8)	C9—C8—H8A	108.2
O5—N5—C5	116.9 (8)	C7—C8—H8A	108.2
N1—C6—O6	118.3 (9)	C9—C8—H8B	108.2
N1—C6—C5	124.7 (9)	C7—C8—H8B	108.2
O6—C6—C5	116.9 (8)	H8A—C8—H8B	107.3
C6—O6—C67	120.0 (7)	O91—C9—O92	124.5 (9)
O6—C67—C61	107.2 (7)	O91—C9—C8	123.3 (8)
O6—C67—H67A	110.3	O92—C9—C8	112.2 (8)
C61—C67—H67A	110.3	C9—O92—C10	114.6 (7)
O6—C67—H67B	110.3	O92—C10—C11	106.8 (7)
C61—C67—H67B	110.3	O92—C10—H10A	110.4
H67A—C67—H67B	108.5	C11—C10—H10A	110.4
C62—C61—C66	120.6 (9)	O92—C10—H10B	110.4
C62—C61—C67	122.1 (9)	C11—C10—H10B	110.4
C66—C61—C67	117.2 (9)	H10A—C10—H10B	108.6
C61—C62—C63	117.9 (10)	C10—C11—H11A	109.5
C61—C62—H62	121.1	C10—C11—H11B	109.5
C63—C62—H62	121.1	H11A—C11—H11B	109.5
C62—C63—C64	122.7 (9)	C10—C11—H11C	109.5
C62—C63—H63	118.7	H11A—C11—H11C	109.5
C64—C63—H63	118.7	H11B—C11—H11C	109.5
C6—N1—C2—N2	179.4 (8)	N1—C6—O6—C67	−4.0 (12)
C6—N1—C2—N3	0.5 (14)	C5—C6—O6—C67	179.4 (9)
N2—C2—N3—C4	−179.5 (8)	C6—O6—C67—C61	179.0 (8)
N1—C2—N3—C4	−0.7 (14)	O6—C67—C61—C62	0.9 (13)
C2—N3—C4—N4	−178.2 (9)	O6—C67—C61—C66	178.9 (9)
C2—N3—C4—C5	2.8 (13)	C66—C61—C62—C63	0.4 (15)
N3—C4—N4—C7	−1.1 (14)	C67—C61—C62—C63	178.4 (9)
C5—C4—N4—C7	177.9 (8)	C61—C62—C63—C64	−0.9 (15)
N4—C4—C5—N5	−0.2 (15)	C62—C63—C64—C65	2.7 (16)
N3—C4—C5—N5	178.7 (9)	C63—C64—C65—C66	−3.9 (16)
N4—C4—C5—C6	176.4 (9)	C64—C65—C66—C61	3.5 (16)
N3—C4—C5—C6	−4.6 (14)	C62—C61—C66—C65	−1.7 (16)
C6—C5—N5—O5	−178.4 (9)	C67—C61—C66—C65	−179.8 (9)
C4—C5—N5—O5	−1.8 (14)	C4—N4—C7—C8	−175.7 (9)
C2—N1—C6—O6	−178.9 (8)	N4—C7—C8—C9	175.0 (8)
C2—N1—C6—C5	−2.6 (14)	C7—C8—C9—O91	−172.2 (9)
N5—C5—C6—N1	−178.4 (8)	C7—C8—C9—O92	9.4 (12)
C4—C5—C6—N1	4.5 (15)	O91—C9—O92—C10	−3.0 (13)
N5—C5—C6—O6	−2.1 (13)	C8—C9—O92—C10	175.3 (7)
C4—C5—C6—O6	−179.1 (8)	C9—O92—C10—C11	−175.1 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O5	0.88	1.93	2.603 (9)	133
N4—H4···O5^i	0.88	2.40	3.223 (10)	156
N2—H2A···N3^ii	0.88	2.18	3.056 (9)	171

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

(5B) Ethyl N-(2-amino-6-benzyloxo-5-nitrosopyrimidin-4-yl)-β-alaninate

Crystal data

C16H19N5O4	F(000) = 728
Mr = 345.36	Dx = 1.364 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 7.4830 (2) Å	Cell parameters from 8888 reflections
b = 16.6110 (6) Å	θ = 1.0–27.5°
c = 13.5378 (6) Å	µ = 0.10 mm^−1
β = 91.5420 (11)°	T = 150 K
V = 1682.14 (11) Å^3	Needle, pink
Z = 4	0.50 × 0.20 × 0.18 mm

Data collection

Kappa-CCD diffractometer	2992 independent reflections
Radiation source: fine-focus sealed X-ray tube	2487 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.083
φ scans, and ω scans with κ offsets	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −8→8
Tmin = 0.951, Tmax = 0.982	k = −19→19
19365 measured reflections	l = −16→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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.149	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.1159P)^2] where P = (Fo^2 + 2Fc^2)/3
2992 reflections	(Δ/σ)max = 0.004
453 parameters	Δρmax = 0.56 e Å^−3
1 restraint	Δρmin = −0.33 e Å^−3

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

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

	x	y	z	Uiso*/Ueq
N11	1.0633 (4)	0.0120 (2)	0.2019 (2)	0.0291 (8)
C110	0.7109 (8)	−0.0180 (5)	0.7469 (4)	0.0727 (18)
C111	0.5954 (8)	−0.0804 (4)	0.7052 (4)	0.0673 (17)
C12	1.2030 (5)	0.0057 (2)	0.2705 (3)	0.0285 (9)
N12	1.3640 (4)	0.0108 (3)	0.2344 (3)	0.0379 (9)
N13	1.1903 (4)	−0.0061 (2)	0.3681 (2)	0.0294 (8)
N14	1.0080 (5)	−0.0300 (2)	0.4985 (3)	0.0345 (8)
C14	1.0259 (5)	−0.0147 (2)	0.4028 (3)	0.0272 (9)
C15	0.8686 (5)	−0.0083 (2)	0.3396 (3)	0.0246 (9)
N15	0.6965 (4)	−0.0158 (2)	0.3646 (2)	0.0279 (8)
O15	0.6638 (3)	−0.03154 (18)	0.4547 (2)	0.0322 (7)
C16	0.9037 (5)	0.0051 (2)	0.2372 (3)	0.0251 (9)
C161	0.6164 (5)	−0.0028 (3)	0.0197 (3)	0.0271 (9)
C162	0.5734 (5)	−0.0806 (3)	−0.0081 (3)	0.0334 (10)
C163	0.4066 (6)	−0.0975 (3)	−0.0512 (3)	0.0429 (12)
C164	0.2853 (6)	−0.0371 (4)	−0.0685 (3)	0.0472 (13)
C165	0.3277 (6)	0.0416 (4)	−0.0419 (3)	0.0467 (13)
C166	0.4949 (6)	0.0587 (3)	0.0012 (3)	0.0335 (10)
C167	0.7930 (5)	0.0145 (3)	0.0705 (3)	0.0307 (10)
O16	0.7601 (3)	0.00849 (17)	0.17628 (19)	0.0286 (7)
C17	1.1556 (5)	−0.0369 (3)	0.5703 (3)	0.0371 (11)
C18	1.1562 (6)	0.0310 (3)	0.6449 (3)	0.0475 (12)
C19	0.9996 (6)	0.0369 (3)	0.7105 (4)	0.0502 (13)
O191	0.9810 (6)	0.0871 (4)	0.7716 (4)	0.0957 (19)
O192	0.8763 (5)	−0.0215 (2)	0.6912 (2)	0.0585 (10)
N21	−0.0683 (4)	0.2105 (2)	0.2997 (2)	0.0321 (8)
C210	0.3345 (7)	0.2998 (4)	−0.2190 (4)	0.0640 (16)
C211	0.4022 (7)	0.2158 (4)	−0.2139 (4)	0.0552 (13)
C22	−0.2057 (5)	0.2146 (3)	0.2309 (3)	0.0279 (9)
N22	−0.3680 (4)	0.2106 (3)	0.2679 (3)	0.0395 (9)
N23	−0.1934 (4)	0.2217 (2)	0.1332 (3)	0.0288 (8)
C24	−0.0286 (5)	0.2268 (2)	0.0973 (3)	0.0245 (8)
N24	−0.0080 (4)	0.2340 (2)	0.0012 (3)	0.0277 (8)
C25	0.1287 (5)	0.2231 (3)	0.1621 (3)	0.0258 (8)
N25	0.3010 (4)	0.2253 (2)	0.1362 (2)	0.0292 (8)
O25	0.3347 (3)	0.23345 (19)	0.0449 (2)	0.0340 (7)
C26	0.0915 (5)	0.2143 (3)	0.2643 (3)	0.0274 (9)
C261	0.3809 (5)	0.2102 (3)	0.4828 (3)	0.0291 (9)
C262	0.4865 (6)	0.1424 (3)	0.4901 (3)	0.0324 (10)
C263	0.6565 (6)	0.1482 (3)	0.5330 (3)	0.0397 (11)
C264	0.7225 (6)	0.2200 (4)	0.5661 (3)	0.0458 (12)
C265	0.6170 (7)	0.2881 (4)	0.5601 (3)	0.0488 (14)
C266	0.4473 (6)	0.2836 (3)	0.5169 (3)	0.0399 (11)
C267	0.2017 (5)	0.2063 (3)	0.4317 (3)	0.0351 (10)
O26	0.2338 (3)	0.2118 (2)	0.32645 (19)	0.0321 (7)
C27	−0.1533 (5)	0.2377 (3)	−0.0735 (3)	0.0324 (10)
C28	−0.1392 (5)	0.3107 (3)	−0.1401 (3)	0.0394 (10)
C29	0.0143 (5)	0.3083 (3)	−0.2087 (3)	0.0368 (10)
O291	0.0006 (5)	0.3144 (3)	−0.2967 (3)	0.0664 (12)
O292	0.1711 (4)	0.3057 (3)	−0.1607 (2)	0.0577 (10)
H11A	0.7361	−0.0281	0.8180	0.087*
H11B	0.6539	0.0356	0.7396	0.087*
H11C	0.5644	−0.0673	0.6363	0.101*
H11D	0.4860	−0.0838	0.7432	0.101*
H11E	0.6578	−0.1323	0.7081	0.101*
H12A	1.4587	0.0064	0.2740	0.045*
H12B	1.3771	0.0186	0.1707	0.045*
H14	0.8989	−0.0363	0.5200	0.041*
H162	0.6578	−0.1226	0.0022	0.040*
H163	0.3768	−0.1513	−0.0687	0.052*
H164	0.1722	−0.0489	−0.0987	0.057*
H165	0.2432	0.0835	−0.0530	0.056*
H166	0.5254	0.1126	0.0180	0.040*
H16A	0.8840	−0.0253	0.0509	0.037*
H16B	0.8354	0.0691	0.0536	0.037*
H17A	1.2699	−0.0366	0.5352	0.045*
H17B	1.1464	−0.0890	0.6054	0.045*
H18A	1.2653	0.0257	0.6874	0.057*
H18B	1.1658	0.0824	0.6085	0.057*
H21A	0.4265	0.3373	−0.1922	0.077*
H21B	0.3073	0.3147	−0.2886	0.077*
H21C	0.4244	0.2007	−0.1447	0.083*
H21D	0.5138	0.2119	−0.2499	0.083*
H21E	0.3131	0.1794	−0.2438	0.083*
H22A	−0.4630	0.2126	0.2282	0.047*
H22B	−0.3805	0.2059	0.3321	0.047*
H24	0.1022	0.2367	−0.0198	0.033*
H262	0.4432	0.0921	0.4661	0.039*
H263	0.7283	0.1012	0.5393	0.048*
H264	0.8406	0.2232	0.5933	0.055*
H265	0.6607	0.3379	0.5854	0.059*
H266	0.3762	0.3308	0.5105	0.048*
H26A	0.1412	0.1550	0.4471	0.042*
H26B	0.1253	0.2514	0.4530	0.042*
H27A	−0.2692	0.2392	−0.0400	0.039*
H27B	−0.1511	0.1883	−0.1144	0.039*
H28A	−0.2516	0.3158	−0.1799	0.047*
H28B	−0.1275	0.3594	−0.0982	0.047*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0231 (18)	0.037 (2)	0.027 (2)	−0.0009 (14)	−0.0014 (13)	0.0005 (16)
C110	0.075 (4)	0.102 (5)	0.042 (3)	−0.016 (4)	0.032 (3)	−0.016 (3)
C111	0.067 (3)	0.091 (5)	0.045 (3)	0.001 (3)	0.016 (3)	0.003 (3)
C12	0.028 (2)	0.026 (2)	0.031 (2)	−0.0016 (16)	0.0044 (17)	−0.0003 (18)
N12	0.0261 (19)	0.060 (3)	0.028 (2)	−0.0050 (16)	0.0040 (14)	−0.0015 (18)
N13	0.0278 (18)	0.040 (2)	0.0207 (19)	−0.0023 (14)	0.0008 (13)	−0.0038 (15)
N14	0.0308 (17)	0.049 (2)	0.0235 (19)	0.0007 (15)	0.0009 (12)	−0.0005 (17)
C14	0.029 (2)	0.026 (2)	0.027 (2)	−0.0022 (16)	0.0014 (16)	−0.0061 (18)
C15	0.020 (2)	0.029 (2)	0.024 (2)	0.0009 (15)	0.0028 (15)	−0.0010 (17)
N15	0.0297 (19)	0.0275 (19)	0.027 (2)	−0.0030 (14)	0.0065 (13)	−0.0037 (15)
O15	0.0314 (15)	0.0401 (18)	0.0257 (17)	−0.0042 (12)	0.0087 (11)	0.0007 (13)
C16	0.020 (2)	0.026 (2)	0.029 (2)	−0.0004 (15)	−0.0010 (15)	−0.0030 (18)
C161	0.029 (2)	0.035 (2)	0.018 (2)	−0.0007 (17)	0.0054 (16)	0.0023 (17)
C162	0.042 (2)	0.030 (2)	0.028 (2)	−0.0002 (18)	0.0008 (18)	−0.0021 (19)
C163	0.050 (3)	0.047 (3)	0.032 (3)	−0.016 (2)	0.0030 (19)	0.000 (2)
C164	0.037 (3)	0.074 (4)	0.030 (3)	−0.012 (2)	−0.0044 (19)	0.007 (2)
C165	0.038 (3)	0.061 (3)	0.041 (3)	0.004 (2)	−0.001 (2)	0.018 (3)
C166	0.034 (2)	0.036 (2)	0.030 (2)	0.0006 (17)	0.0035 (16)	0.0045 (19)
C167	0.033 (2)	0.039 (2)	0.021 (2)	−0.0047 (17)	0.0045 (15)	0.0007 (19)
O16	0.0241 (14)	0.0408 (17)	0.0210 (15)	0.0017 (11)	0.0009 (10)	0.0000 (13)
C17	0.031 (2)	0.058 (3)	0.023 (2)	0.0034 (19)	−0.0031 (17)	0.002 (2)
C18	0.046 (3)	0.060 (3)	0.036 (3)	−0.004 (2)	−0.0037 (19)	−0.001 (2)
C19	0.053 (3)	0.060 (3)	0.037 (3)	0.008 (2)	−0.010 (2)	−0.011 (3)
O191	0.073 (3)	0.115 (5)	0.098 (4)	0.006 (3)	0.002 (2)	−0.069 (4)
O192	0.062 (2)	0.075 (3)	0.040 (2)	−0.0073 (19)	0.0167 (16)	−0.0088 (18)
N21	0.0221 (17)	0.044 (2)	0.030 (2)	0.0027 (15)	0.0043 (13)	0.0073 (17)
C210	0.057 (3)	0.084 (4)	0.052 (3)	0.011 (3)	0.026 (2)	0.015 (3)
C211	0.052 (3)	0.061 (3)	0.054 (3)	−0.004 (3)	0.019 (2)	−0.004 (3)
C22	0.025 (2)	0.035 (2)	0.024 (2)	0.0026 (18)	−0.0008 (15)	0.0044 (19)
N22	0.0226 (18)	0.068 (3)	0.028 (2)	0.0045 (17)	0.0027 (13)	0.009 (2)
N23	0.0184 (17)	0.032 (2)	0.036 (2)	0.0000 (14)	0.0015 (13)	0.0053 (16)
C24	0.025 (2)	0.022 (2)	0.026 (2)	0.0003 (16)	−0.0004 (15)	0.0037 (17)
N24	0.0183 (15)	0.038 (2)	0.0267 (18)	−0.0018 (13)	−0.0011 (12)	0.0042 (16)
C25	0.022 (2)	0.026 (2)	0.029 (2)	−0.0010 (17)	−0.0009 (15)	0.0009 (18)
N25	0.0265 (18)	0.033 (2)	0.028 (2)	0.0011 (15)	0.0012 (13)	0.0034 (16)
O25	0.0270 (15)	0.048 (2)	0.0275 (17)	−0.0005 (12)	0.0033 (11)	0.0066 (14)
C26	0.026 (2)	0.031 (2)	0.025 (2)	0.0023 (18)	−0.0012 (15)	0.0045 (19)
C261	0.029 (2)	0.039 (3)	0.020 (2)	0.0020 (18)	0.0042 (16)	0.0019 (19)
C262	0.038 (2)	0.034 (2)	0.025 (2)	−0.0031 (17)	0.0002 (17)	−0.0030 (19)
C263	0.030 (2)	0.051 (3)	0.037 (3)	0.0070 (19)	−0.0027 (18)	−0.003 (2)
C264	0.036 (2)	0.068 (3)	0.033 (3)	−0.012 (3)	−0.0042 (18)	−0.003 (3)
C265	0.064 (3)	0.056 (3)	0.026 (3)	−0.027 (3)	0.000 (2)	−0.007 (2)
C266	0.054 (3)	0.037 (3)	0.029 (3)	0.001 (2)	0.0051 (19)	0.000 (2)
C267	0.030 (2)	0.052 (3)	0.023 (2)	0.0076 (19)	−0.0005 (16)	0.003 (2)
O26	0.0209 (14)	0.0511 (18)	0.0240 (16)	0.0019 (13)	−0.0019 (10)	0.0034 (14)
C27	0.025 (2)	0.039 (3)	0.033 (3)	−0.0006 (16)	−0.0029 (16)	−0.0007 (19)
C28	0.026 (2)	0.049 (3)	0.043 (3)	−0.0013 (18)	−0.0104 (16)	0.008 (2)
C29	0.040 (2)	0.044 (3)	0.026 (2)	−0.0092 (19)	−0.0082 (17)	0.005 (2)
O291	0.075 (3)	0.092 (3)	0.031 (2)	−0.035 (2)	−0.0116 (16)	0.0106 (19)
O292	0.0359 (17)	0.103 (3)	0.0350 (19)	0.0141 (18)	0.0091 (13)	0.013 (2)

Geometric parameters (Å, º)

N11—C16	1.304 (5)	N21—C26	1.301 (5)
N11—C12	1.383 (5)	N21—C22	1.371 (5)
C110—C111	1.455 (9)	C210—O292	1.477 (5)
C110—O192	1.468 (6)	C210—C211	1.485 (9)
C110—H11A	0.9900	C210—H21A	0.9900
C110—H11B	0.9900	C210—H21B	0.9900
C111—H11C	0.9800	C211—H21C	0.9800
C111—H11D	0.9800	C211—H21D	0.9800
C111—H11E	0.9800	C211—H21E	0.9800
C12—N12	1.314 (5)	C22—N22	1.327 (5)
C12—N13	1.342 (5)	C22—N23	1.333 (5)
N12—H12A	0.8800	N22—H22A	0.8800
N12—H12B	0.8800	N22—H22B	0.8800
N13—C14	1.336 (5)	N23—C24	1.340 (5)
N14—C14	1.330 (6)	C24—N24	1.320 (5)
N14—C17	1.456 (5)	C24—C25	1.450 (5)
N14—H14	0.8800	N24—C27	1.466 (5)
C14—C15	1.441 (5)	N24—H24	0.8800
C15—N15	1.346 (5)	C25—N25	1.345 (5)
C15—C16	1.435 (6)	C25—C26	1.427 (5)
N15—O15	1.277 (4)	N25—O25	1.276 (4)
C16—O16	1.338 (4)	C26—O26	1.340 (4)
C161—C162	1.381 (6)	C261—C262	1.378 (6)
C161—C166	1.386 (6)	C261—C266	1.391 (7)
C161—C167	1.500 (5)	C261—C267	1.494 (5)
C162—C163	1.392 (6)	C262—C263	1.388 (6)
C162—H162	0.9500	C262—H262	0.9500
C163—C164	1.369 (7)	C263—C264	1.362 (7)
C163—H163	0.9500	C263—H263	0.9500
C164—C165	1.390 (8)	C264—C265	1.380 (8)
C164—H164	0.9500	C264—H264	0.9500
C165—C166	1.395 (6)	C265—C266	1.386 (7)
C165—H165	0.9500	C265—H265	0.9500
C166—H166	0.9500	C266—H266	0.9500
C167—O16	1.463 (5)	C267—O26	1.454 (5)
C167—H16A	0.9900	C267—H26A	0.9900
C167—H16B	0.9900	C267—H26B	0.9900
C17—C18	1.514 (7)	C27—C28	1.517 (6)
C17—H17A	0.9900	C27—H27A	0.9900
C17—H17B	0.9900	C27—H27B	0.9900
C18—C19	1.492 (6)	C28—C29	1.498 (6)
C18—H18A	0.9900	C28—H28A	0.9900
C18—H18B	0.9900	C28—H28B	0.9900
C19—O191	1.185 (6)	C29—O291	1.197 (5)
C19—O192	1.359 (6)	C29—O292	1.326 (5)
C16—N11—C12	115.5 (3)	C26—N21—C22	115.3 (3)
C111—C110—O192	105.8 (5)	O292—C210—C211	108.9 (5)
C111—C110—H11A	110.6	O292—C210—H21A	109.9
O192—C110—H11A	110.6	C211—C210—H21A	109.9
C111—C110—H11B	110.6	O292—C210—H21B	109.9
O192—C110—H11B	110.6	C211—C210—H21B	109.9
H11A—C110—H11B	108.7	H21A—C210—H21B	108.3
C110—C111—H11C	109.5	C210—C211—H21C	109.5
C110—C111—H11D	109.5	C210—C211—H21D	109.5
H11C—C111—H11D	109.5	H21C—C211—H21D	109.5
C110—C111—H11E	109.5	C210—C211—H21E	109.5
H11C—C111—H11E	109.5	H21C—C211—H21E	109.5
H11D—C111—H11E	109.5	H21D—C211—H21E	109.5
N12—C12—N13	117.7 (4)	N22—C22—N23	117.8 (3)
N12—C12—N11	115.5 (4)	N22—C22—N21	114.7 (3)
N13—C12—N11	126.8 (3)	N23—C22—N21	127.4 (3)
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
C14—N13—C12	116.9 (3)	C22—N23—C24	117.0 (3)
C14—N14—C17	124.8 (3)	N24—C24—N23	119.8 (3)
C14—N14—H14	117.6	N24—C24—C25	119.0 (3)
C17—N14—H14	117.6	N23—C24—C25	121.2 (4)
N14—C14—N13	118.7 (4)	C24—N24—C27	125.4 (3)
N14—C14—C15	119.4 (3)	C24—N24—H24	117.3
N13—C14—C15	121.9 (4)	C27—N24—H24	117.3
N15—C15—C16	117.3 (3)	N25—C25—C26	117.9 (3)
N15—C15—C14	128.0 (4)	N25—C25—C24	127.6 (4)
C16—C15—C14	114.7 (3)	C26—C25—C24	114.5 (3)
O15—N15—C15	118.0 (3)	O25—N25—C25	118.1 (3)
N11—C16—O16	120.0 (4)	N21—C26—O26	119.3 (3)
N11—C16—C15	124.1 (3)	N21—C26—C25	124.6 (3)
O16—C16—C15	115.9 (3)	O26—C26—C25	116.1 (3)
C162—C161—C166	119.5 (4)	C262—C261—C266	119.6 (4)
C162—C161—C167	120.0 (4)	C262—C261—C267	120.3 (4)
C166—C161—C167	120.5 (4)	C266—C261—C267	120.0 (4)
C161—C162—C163	120.2 (4)	C261—C262—C263	119.4 (4)
C161—C162—H162	119.9	C261—C262—H262	120.3
C163—C162—H162	119.9	C263—C262—H262	120.3
C164—C163—C162	120.4 (5)	C264—C263—C262	121.2 (4)
C164—C163—H163	119.8	C264—C263—H263	119.4
C162—C163—H163	119.8	C262—C263—H263	119.4
C163—C164—C165	119.9 (4)	C263—C264—C265	119.8 (4)
C163—C164—H164	120.0	C263—C264—H264	120.1
C165—C164—H164	120.0	C265—C264—H264	120.1
C164—C165—C166	119.7 (5)	C264—C265—C266	119.8 (5)
C164—C165—H165	120.1	C264—C265—H265	120.1
C166—C165—H165	120.1	C266—C265—H265	120.1
C161—C166—C165	120.1 (4)	C265—C266—C261	120.2 (4)
C161—C166—H166	119.9	C265—C266—H266	119.9
C165—C166—H166	119.9	C261—C266—H266	119.9
O16—C167—C161	105.4 (3)	O26—C267—C261	106.4 (3)
O16—C167—H16A	110.7	O26—C267—H26A	110.5
C161—C167—H16A	110.7	C261—C267—H26A	110.5
O16—C167—H16B	110.7	O26—C267—H26B	110.5
C161—C167—H16B	110.7	C261—C267—H26B	110.5
H16A—C167—H16B	108.8	H26A—C267—H26B	108.6
C16—O16—C167	116.9 (3)	C26—O26—C267	117.9 (3)
N14—C17—C18	112.0 (4)	N24—C27—C28	112.4 (3)
N14—C17—H17A	109.2	N24—C27—H27A	109.1
C18—C17—H17A	109.2	C28—C27—H27A	109.1
N14—C17—H17B	109.2	N24—C27—H27B	109.1
C18—C17—H17B	109.2	C28—C27—H27B	109.1
H17A—C17—H17B	107.9	H27A—C27—H27B	107.9
C19—C18—C17	117.2 (4)	C29—C28—C27	114.4 (4)
C19—C18—H18A	108.0	C29—C28—H28A	108.7
C17—C18—H18A	108.0	C27—C28—H28A	108.6
C19—C18—H18B	108.0	C29—C28—H28B	108.6
C17—C18—H18B	108.0	C27—C28—H28B	108.6
H18A—C18—H18B	107.2	H28A—C28—H28B	107.6
O191—C19—O192	123.0 (5)	O291—C29—O292	122.8 (4)
O191—C19—C18	124.7 (5)	O291—C29—C28	124.6 (4)
O192—C19—C18	112.3 (4)	O292—C29—C28	112.3 (3)
C19—O192—C110	116.8 (4)	C29—O292—C210	118.3 (4)
C16—N11—C12—N12	178.5 (4)	C26—N21—C22—N22	179.9 (4)
C16—N11—C12—N13	−0.3 (6)	C26—N21—C22—N23	0.4 (7)
N12—C12—N13—C14	−177.1 (4)	N22—C22—N23—C24	179.1 (4)
N11—C12—N13—C14	1.6 (6)	N21—C22—N23—C24	−1.3 (7)
C17—N14—C14—N13	1.1 (6)	C22—N23—C24—N24	−179.9 (4)
C17—N14—C14—C15	−179.2 (4)	C22—N23—C24—C25	1.3 (6)
C12—N13—C14—N14	177.2 (4)	N23—C24—N24—C27	0.6 (6)
C12—N13—C14—C15	−2.5 (6)	C25—C24—N24—C27	179.4 (4)
N14—C14—C15—N15	0.2 (6)	N24—C24—C25—N25	−0.7 (6)
N13—C14—C15—N15	179.8 (4)	N23—C24—C25—N25	178.1 (4)
N14—C14—C15—C16	−177.6 (4)	N24—C24—C25—C26	−179.2 (4)
N13—C14—C15—C16	2.0 (5)	N23—C24—C25—C26	−0.4 (6)
C16—C15—N15—O15	176.7 (4)	C26—C25—N25—O25	−179.8 (4)
C14—C15—N15—O15	−1.0 (6)	C24—C25—N25—O25	1.8 (6)
C12—N11—C16—O16	−178.5 (3)	C22—N21—C26—O26	179.1 (4)
C12—N11—C16—C15	−0.2 (6)	C22—N21—C26—C25	0.7 (6)
N15—C15—C16—N11	−178.6 (4)	N25—C25—C26—N21	−179.3 (4)
C14—C15—C16—N11	−0.6 (6)	C24—C25—C26—N21	−0.7 (6)
N15—C15—C16—O16	−0.2 (5)	N25—C25—C26—O26	2.3 (6)
C14—C15—C16—O16	177.8 (3)	C24—C25—C26—O26	−179.1 (4)
C166—C161—C162—C163	−2.3 (6)	C266—C261—C262—C263	1.1 (6)
C167—C161—C162—C163	177.1 (4)	C267—C261—C262—C263	176.4 (4)
C161—C162—C163—C164	1.5 (7)	C261—C262—C263—C264	−1.3 (7)
C162—C163—C164—C165	−0.8 (7)	C262—C263—C264—C265	2.0 (7)
C163—C164—C165—C166	0.8 (7)	C263—C264—C265—C266	−2.5 (7)
C162—C161—C166—C165	2.3 (7)	C264—C265—C266—C261	2.3 (7)
C167—C161—C166—C165	−177.0 (4)	C262—C261—C266—C265	−1.6 (6)
C164—C165—C166—C161	−1.6 (7)	C267—C261—C266—C265	−176.9 (4)
C162—C161—C167—O16	−91.8 (4)	C262—C261—C267—O26	−81.0 (5)
C166—C161—C167—O16	87.6 (4)	C266—C261—C267—O26	94.2 (5)
N11—C16—O16—C167	4.1 (5)	N21—C26—O26—C267	−1.1 (6)
C15—C16—O16—C167	−174.4 (3)	C25—C26—O26—C267	177.5 (4)
C161—C167—O16—C16	166.7 (3)	C261—C267—O26—C26	−176.2 (4)
C14—N14—C17—C18	112.8 (5)	C24—N24—C27—C28	126.5 (4)
N14—C17—C18—C19	63.1 (5)	N24—C27—C28—C29	69.2 (5)
C17—C18—C19—O191	−179.3 (6)	C27—C28—C29—O291	123.9 (5)
C17—C18—C19—O192	−0.6 (6)	C27—C28—C29—O292	−61.7 (5)
O191—C19—O192—C110	2.8 (8)	O291—C29—O292—C210	−8.0 (7)
C18—C19—O192—C110	−175.9 (5)	C28—C29—O292—C210	177.6 (5)
C111—C110—O192—C19	173.8 (5)	C211—C210—O292—C29	−103.5 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N14—H14···O15	0.88	1.95	2.628 (4)	133
N24—H24···O25	0.88	1.93	2.616 (4)	134
N12—H12A···N15^i	0.88	2.17	3.042 (5)	174
N22—H22A···N25^ii	0.88	2.14	3.023 (4)	176

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

(6) Ethyl N-(2-amino-6-benzyloxy-5-nitrosopyrimidin-4-yl)-L-phenylalaninate

Crystal data

C22H23N5O4	Z = 2
Mr = 421.45	F(000) = 444
Triclinic, P1	Dx = 1.338 Mg m^−3
a = 7.9899 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.4278 (3) Å	Cell parameters from 14344 reflections
c = 17.0042 (7) Å	θ = 2.9–27.5°
α = 99.9100 (12)°	µ = 0.10 mm^−1
β = 90.5610 (13)°	T = 150 K
γ = 111.4880 (17)°	Plate, pink
V = 1046.22 (7) Å^3	0.30 × 0.20 × 0.03 mm

Data collection

Kappa-CCD diffractometer	8664 independent reflections
Radiation source: fine-focus sealed X-ray tube	6321 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
φ scans and ω scans with κ offsets	θmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan Sortav (Blessing, 1995 & 1997)	h = −10→10
Tmin = 0.972, Tmax = 0.997	k = −10→10
14846 measured reflections	l = −22→22

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.110	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0638P)^2] where P = (Fo^2 + 2Fc^2)/3
4686 reflections	(Δ/σ)max < 0.001
561 parameters	Δρmax = 0.20 e Å^−3
3 restraints	Δρmin = −0.24 e Å^−3

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Geometry. Mean-plane data from the final SHELXL97 refinement run:-

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

	x	y	z	Uiso*/Ueq
N11	0.0293 (3)	−0.2813 (3)	0.02734 (15)	0.0246 (5)
C12	0.1004 (4)	−0.3196 (4)	0.09199 (17)	0.0237 (6)
N12	0.0819 (4)	−0.4846 (3)	0.08480 (16)	0.0293 (6)
N13	0.1826 (3)	−0.2111 (3)	0.16057 (15)	0.0240 (5)
C14	0.2072 (4)	−0.0452 (4)	0.16334 (17)	0.0223 (6)
N14	0.2901 (3)	0.0711 (3)	0.22901 (14)	0.0250 (6)
C15	0.1471 (4)	0.0160 (4)	0.09847 (17)	0.0216 (6)
N15	0.1604 (3)	0.1771 (3)	0.09448 (15)	0.0262 (6)
O15	0.2394 (3)	0.2984 (2)	0.15520 (13)	0.0306 (5)
C16	0.0545 (4)	−0.1182 (4)	0.03139 (17)	0.0227 (6)
O16	−0.0073 (3)	−0.0666 (3)	−0.02881 (12)	0.0275 (5)
C167	−0.0932 (4)	−0.1948 (4)	−0.10057 (18)	0.0287 (7)
C161	0.0472 (4)	−0.2161 (4)	−0.15633 (18)	0.0272 (7)
C162	0.1141 (5)	−0.3435 (4)	−0.1546 (2)	0.0357 (8)
C163	0.2414 (5)	−0.3636 (5)	−0.2058 (2)	0.0439 (9)
C164	0.3039 (5)	−0.2517 (5)	−0.2592 (2)	0.0471 (9)
C165	0.2371 (5)	−0.1228 (4)	−0.2609 (2)	0.0388 (8)
C166	0.1097 (5)	−0.1046 (4)	−0.21054 (19)	0.0324 (7)
C17	0.3394 (4)	0.0235 (4)	0.30105 (18)	0.0255 (6)
C177	0.4611 (4)	0.1883 (4)	0.35974 (18)	0.0296 (7)
C171	0.6462 (4)	0.2759 (4)	0.33286 (17)	0.0262 (7)
C172	0.7875 (5)	0.2307 (4)	0.3533 (2)	0.0348 (7)
C173	0.9596 (5)	0.3103 (5)	0.3295 (2)	0.0376 (8)
C174	0.9908 (5)	0.4387 (4)	0.2848 (2)	0.0372 (8)
C175	0.8518 (5)	0.4869 (4)	0.26380 (19)	0.0347 (8)
C176	0.6808 (4)	0.4062 (4)	0.28762 (19)	0.0308 (7)
C18	0.1706 (4)	−0.0666 (4)	0.34322 (18)	0.0275 (7)
O181	0.0266 (3)	−0.0607 (3)	0.33049 (14)	0.0387 (6)
O182	0.2141 (3)	−0.1407 (3)	0.39837 (13)	0.0337 (5)
C19	0.0717 (4)	−0.2167 (4)	0.4498 (2)	0.0343 (7)
C110	0.1538 (5)	−0.2719 (6)	0.5128 (3)	0.0509 (10)
N21	0.4828 (3)	0.2320 (3)	−0.04116 (15)	0.0274 (6)
C22	0.3976 (4)	0.2719 (4)	−0.10001 (18)	0.0240 (6)
N22	0.2352 (3)	0.2700 (3)	−0.08595 (16)	0.0293 (6)
N23	0.4645 (3)	0.3201 (3)	−0.16885 (15)	0.0245 (5)
C24	0.6208 (4)	0.3054 (4)	−0.18474 (18)	0.0237 (6)
N24	0.6952 (3)	0.3525 (3)	−0.25112 (15)	0.0280 (6)
C25	0.7164 (4)	0.2455 (4)	−0.13176 (19)	0.0262 (7)
N25	0.8677 (4)	0.2153 (4)	−0.14242 (17)	0.0344 (6)
O25	0.9404 (3)	0.2381 (3)	−0.20923 (15)	0.0399 (6)
C26	0.6390 (4)	0.2230 (4)	−0.05630 (18)	0.0250 (6)
O26	0.7375 (3)	0.1916 (3)	−0.00212 (13)	0.0354 (5)
C267	0.6668 (5)	0.1644 (4)	0.07555 (19)	0.0334 (8)
C261	0.6380 (4)	−0.0157 (4)	0.0852 (2)	0.0291 (7)
C262	0.5376 (5)	−0.1581 (5)	0.0281 (2)	0.0467 (10)
C263	0.5142 (6)	−0.3246 (5)	0.0412 (4)	0.0704 (17)
C264	0.5878 (7)	−0.3473 (6)	0.1109 (4)	0.0721 (16)
C265	0.6852 (6)	−0.2060 (6)	0.1665 (3)	0.0595 (12)
C266	0.7104 (5)	−0.0426 (5)	0.1543 (2)	0.0371 (8)
C27	0.6230 (4)	0.4392 (4)	−0.30142 (18)	0.0260 (7)
C277	0.7688 (4)	0.5249 (4)	−0.3556 (2)	0.0290 (7)
C271	0.7171 (4)	0.6401 (4)	−0.40159 (19)	0.0291 (7)
C272	0.6541 (5)	0.5842 (5)	−0.4818 (2)	0.0369 (8)
C273	0.6065 (5)	0.6922 (6)	−0.5229 (2)	0.0464 (9)
C274	0.6180 (5)	0.8537 (6)	−0.4845 (3)	0.0486 (10)
C275	0.6814 (5)	0.9103 (5)	−0.4047 (2)	0.0441 (9)
C276	0.7310 (4)	0.8037 (4)	−0.3643 (2)	0.0357 (8)
C28	0.4558 (4)	0.3088 (4)	−0.3519 (2)	0.0319 (7)
O281	0.4513 (4)	0.1771 (3)	−0.39268 (19)	0.0582 (8)
O282	0.3187 (3)	0.3594 (4)	−0.34457 (15)	0.0477 (7)
C29	0.1453 (5)	0.2399 (7)	−0.3849 (3)	0.0615 (12)
C210	0.1270 (7)	0.2630 (6)	−0.4673 (3)	0.0672 (13)
H12A	0.1476	−0.5155	0.1163	0.035*
H12B	0.0202	−0.5584	0.0415	0.035*
H14	0.3160	0.1818	0.2285	0.030*
H16A	−0.1777	−0.1576	−0.1285	0.034*
H16B	−0.1633	−0.3076	−0.0855	0.034*
H162	0.0725	−0.4194	−0.1175	0.043*
H163	0.2857	−0.4535	−0.2044	0.053*
H164	0.3919	−0.2637	−0.2944	0.057*
H165	0.2798	−0.0458	−0.2974	0.047*
H166	0.0639	−0.0159	−0.2126	0.039*
H17	0.4058	−0.0563	0.2871	0.031*
H17A	0.4000	0.2724	0.3676	0.035*
H17B	0.4746	0.1567	0.4122	0.035*
H172	0.7669	0.1429	0.3844	0.042*
H173	1.0550	0.2765	0.3439	0.045*
H174	1.1081	0.4940	0.2685	0.045*
H175	0.8732	0.5753	0.2330	0.042*
H176	0.5856	0.4402	0.2729	0.037*
H19A	−0.0273	−0.3175	0.4181	0.041*
H19B	0.0216	−0.1298	0.4741	0.041*
H11A	0.2466	−0.1700	0.5457	0.076*
H11B	0.2087	−0.3528	0.4879	0.076*
H11C	0.0605	−0.3296	0.5466	0.076*
H22A	0.1615	0.2775	−0.1231	0.035*
H22B	0.1805	0.2268	−0.0453	0.035*
H24	0.7914	0.3303	−0.2649	0.034*
H26A	0.5513	0.1825	0.0787	0.040*
H26B	0.7533	0.2488	0.1191	0.040*
H262	0.4852	−0.1437	−0.0193	0.056*
H263	0.4471	−0.4234	0.0019	0.085*
H264	0.5699	−0.4606	0.1195	0.087*
H265	0.7364	−0.2203	0.2142	0.071*
H266	0.7790	0.0548	0.1940	0.045*
H27	0.5906	0.5306	−0.2668	0.031*
H27A	0.8828	0.5948	−0.3223	0.035*
H27B	0.7906	0.4332	−0.3940	0.035*
H272	0.6434	0.4719	−0.5085	0.044*
H273	0.5657	0.6541	−0.5781	0.056*
H274	0.5826	0.9259	−0.5126	0.058*
H275	0.6908	1.0221	−0.3778	0.053*
H276	0.7757	0.8439	−0.3096	0.043*
H29A	0.0467	0.2600	−0.3552	0.074*
H29B	0.1342	0.1190	−0.3849	0.074*
H21A	0.2190	0.2346	−0.4978	0.101*
H21B	0.1430	0.3839	−0.4674	0.101*
H21C	0.0068	0.1861	−0.4918	0.101*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0281 (13)	0.0235 (13)	0.0228 (13)	0.0103 (11)	0.0018 (10)	0.0044 (10)
C12	0.0249 (14)	0.0270 (16)	0.0223 (16)	0.0115 (13)	0.0065 (12)	0.0081 (12)
N12	0.0356 (14)	0.0240 (13)	0.0295 (14)	0.0127 (12)	−0.0019 (11)	0.0051 (11)
N13	0.0267 (13)	0.0198 (12)	0.0242 (14)	0.0062 (10)	0.0038 (10)	0.0060 (10)
C14	0.0240 (14)	0.0240 (15)	0.0195 (15)	0.0090 (12)	0.0039 (11)	0.0056 (11)
N14	0.0338 (13)	0.0174 (12)	0.0214 (13)	0.0063 (11)	−0.0011 (10)	0.0050 (10)
C15	0.0229 (14)	0.0226 (14)	0.0223 (15)	0.0104 (12)	0.0067 (12)	0.0076 (11)
N15	0.0311 (14)	0.0234 (13)	0.0228 (14)	0.0087 (11)	0.0041 (11)	0.0038 (10)
O15	0.0412 (13)	0.0199 (10)	0.0263 (12)	0.0075 (10)	−0.0025 (9)	0.0025 (9)
C16	0.0231 (14)	0.0278 (16)	0.0197 (15)	0.0125 (13)	0.0038 (12)	0.0041 (11)
O16	0.0360 (12)	0.0284 (11)	0.0206 (11)	0.0159 (10)	−0.0004 (9)	0.0029 (8)
C167	0.0329 (17)	0.0324 (17)	0.0220 (16)	0.0149 (14)	−0.0035 (13)	0.0026 (12)
C161	0.0330 (16)	0.0261 (15)	0.0193 (16)	0.0100 (13)	−0.0047 (12)	−0.0015 (12)
C162	0.046 (2)	0.0350 (18)	0.0306 (18)	0.0185 (16)	0.0071 (15)	0.0099 (14)
C163	0.057 (2)	0.044 (2)	0.044 (2)	0.0311 (18)	0.0186 (18)	0.0145 (16)
C164	0.057 (2)	0.051 (2)	0.038 (2)	0.025 (2)	0.0194 (18)	0.0103 (17)
C165	0.051 (2)	0.0291 (17)	0.0302 (19)	0.0075 (16)	0.0073 (15)	0.0072 (14)
C166	0.0436 (19)	0.0271 (16)	0.0256 (17)	0.0137 (15)	−0.0025 (14)	0.0015 (13)
C17	0.0305 (16)	0.0258 (15)	0.0199 (15)	0.0081 (13)	0.0006 (12)	0.0088 (12)
C177	0.0320 (16)	0.0295 (16)	0.0217 (16)	0.0047 (14)	0.0010 (13)	0.0056 (13)
C171	0.0303 (17)	0.0233 (15)	0.0200 (15)	0.0059 (13)	0.0001 (12)	0.0010 (12)
C172	0.0388 (18)	0.0320 (17)	0.0317 (18)	0.0098 (15)	−0.0011 (14)	0.0094 (13)
C173	0.0337 (18)	0.0383 (19)	0.039 (2)	0.0126 (16)	−0.0008 (15)	0.0049 (15)
C174	0.0331 (18)	0.0371 (18)	0.0331 (19)	0.0063 (15)	0.0091 (15)	−0.0003 (15)
C175	0.0420 (19)	0.0322 (17)	0.0276 (18)	0.0110 (16)	0.0063 (14)	0.0058 (14)
C176	0.0346 (17)	0.0303 (16)	0.0275 (17)	0.0136 (15)	0.0007 (13)	0.0021 (13)
C18	0.0327 (17)	0.0243 (15)	0.0241 (17)	0.0083 (13)	−0.0006 (13)	0.0058 (12)
O181	0.0346 (13)	0.0420 (13)	0.0416 (14)	0.0134 (11)	0.0014 (11)	0.0157 (11)
O182	0.0333 (12)	0.0388 (12)	0.0298 (12)	0.0099 (10)	0.0060 (9)	0.0162 (10)
C19	0.0329 (17)	0.0371 (18)	0.0303 (17)	0.0074 (15)	0.0095 (14)	0.0121 (14)
C110	0.045 (2)	0.070 (3)	0.047 (2)	0.022 (2)	0.0150 (18)	0.034 (2)
N21	0.0278 (13)	0.0327 (14)	0.0247 (14)	0.0140 (12)	0.0018 (11)	0.0071 (11)
C22	0.0240 (15)	0.0214 (15)	0.0269 (16)	0.0091 (13)	0.0014 (12)	0.0041 (12)
N22	0.0242 (13)	0.0375 (15)	0.0293 (15)	0.0144 (12)	0.0024 (11)	0.0076 (12)
N23	0.0237 (12)	0.0276 (13)	0.0242 (14)	0.0110 (11)	0.0028 (10)	0.0070 (10)
C24	0.0244 (15)	0.0247 (15)	0.0240 (16)	0.0116 (13)	0.0005 (12)	0.0045 (12)
N24	0.0272 (13)	0.0384 (15)	0.0276 (14)	0.0201 (12)	0.0069 (11)	0.0130 (11)
C25	0.0226 (14)	0.0307 (16)	0.0285 (17)	0.0116 (13)	0.0017 (12)	0.0103 (13)
N25	0.0309 (14)	0.0433 (16)	0.0373 (16)	0.0178 (13)	0.0109 (12)	0.0197 (13)
O25	0.0358 (13)	0.0585 (16)	0.0427 (14)	0.0290 (12)	0.0181 (11)	0.0282 (12)
C26	0.0231 (15)	0.0272 (16)	0.0274 (17)	0.0109 (13)	−0.0004 (12)	0.0085 (12)
O26	0.0353 (13)	0.0530 (15)	0.0289 (13)	0.0234 (11)	0.0054 (10)	0.0205 (11)
C267	0.0422 (19)	0.0419 (19)	0.0191 (16)	0.0185 (16)	−0.0008 (14)	0.0073 (14)
C261	0.0253 (15)	0.0305 (17)	0.0307 (18)	0.0097 (13)	0.0086 (13)	0.0045 (13)
C262	0.0363 (19)	0.047 (2)	0.042 (2)	0.0055 (18)	0.0061 (16)	−0.0058 (17)
C263	0.054 (3)	0.030 (2)	0.099 (4)	−0.006 (2)	0.038 (3)	−0.017 (2)
C264	0.074 (3)	0.041 (3)	0.114 (5)	0.027 (3)	0.053 (3)	0.034 (3)
C265	0.068 (3)	0.056 (3)	0.075 (3)	0.035 (2)	0.031 (2)	0.040 (3)
C266	0.0398 (19)	0.044 (2)	0.036 (2)	0.0227 (17)	0.0060 (15)	0.0149 (16)
C27	0.0284 (15)	0.0312 (16)	0.0261 (16)	0.0178 (14)	0.0055 (12)	0.0098 (13)
C277	0.0248 (15)	0.0330 (17)	0.0307 (17)	0.0107 (14)	0.0049 (13)	0.0100 (13)
C271	0.0214 (15)	0.0361 (18)	0.0297 (17)	0.0098 (14)	0.0023 (12)	0.0080 (13)
C272	0.0378 (18)	0.0392 (19)	0.0317 (19)	0.0111 (16)	0.0030 (14)	0.0089 (14)
C273	0.045 (2)	0.066 (3)	0.035 (2)	0.022 (2)	0.0055 (16)	0.0225 (19)
C274	0.039 (2)	0.063 (3)	0.060 (3)	0.0250 (19)	0.0091 (18)	0.039 (2)
C275	0.0362 (19)	0.036 (2)	0.063 (3)	0.0152 (17)	0.0077 (18)	0.0120 (18)
C276	0.0322 (17)	0.0335 (18)	0.040 (2)	0.0113 (15)	0.0000 (14)	0.0054 (14)
C28	0.0324 (18)	0.0337 (18)	0.0367 (19)	0.0160 (15)	0.0036 (14)	0.0170 (15)
O281	0.0538 (16)	0.0290 (14)	0.088 (2)	0.0187 (13)	−0.0222 (15)	−0.0056 (14)
O282	0.0350 (13)	0.0757 (18)	0.0347 (14)	0.0275 (13)	−0.0034 (11)	0.0011 (12)
C29	0.0309 (19)	0.102 (4)	0.047 (2)	0.018 (2)	−0.0045 (17)	0.016 (2)
C210	0.075 (3)	0.060 (3)	0.060 (3)	0.015 (2)	−0.021 (2)	0.019 (2)

Geometric parameters (Å, º)

N11—C16	1.303 (4)	N21—C26	1.303 (4)
N11—C12	1.371 (4)	N21—C22	1.359 (4)
C12—N12	1.327 (4)	C22—N22	1.317 (4)
C12—N13	1.344 (4)	C22—N23	1.356 (4)
N12—H12A	0.8784	N22—H22A	0.8853
N12—H12B	0.8842	N22—H22B	0.8806
N13—C14	1.331 (4)	N23—C24	1.325 (4)
C14—N14	1.334 (4)	C24—N24	1.334 (4)
C14—C15	1.442 (4)	C24—C25	1.441 (4)
N14—C17	1.446 (4)	N24—C27	1.453 (4)
N14—H14	0.8800	N24—H24	0.8800
C15—N15	1.336 (4)	C25—N25	1.332 (4)
C15—C16	1.433 (4)	C25—C26	1.442 (4)
N15—O15	1.289 (3)	N25—O25	1.292 (3)
C16—O16	1.335 (4)	C26—O26	1.327 (4)
O16—C167	1.454 (4)	O26—C267	1.463 (4)
C167—C161	1.516 (5)	C267—C261	1.488 (5)
C167—H16A	0.9900	C267—H26A	0.9900
C167—H16B	0.9900	C267—H26B	0.9900
C161—C162	1.367 (5)	C261—C262	1.380 (5)
C161—C166	1.395 (5)	C261—C266	1.394 (5)
C162—C163	1.384 (5)	C262—C263	1.405 (7)
C162—H162	0.9500	C262—H262	0.9500
C163—C164	1.387 (5)	C263—C264	1.390 (8)
C163—H163	0.9500	C263—H263	0.9500
C164—C165	1.378 (5)	C264—C265	1.355 (8)
C164—H164	0.9500	C264—H264	0.9500
C165—C166	1.371 (5)	C265—C266	1.369 (5)
C165—H165	0.9500	C265—H265	0.9500
C166—H166	0.9500	C266—H266	0.9500
C17—C18	1.538 (4)	C27—C28	1.519 (4)
C17—C177	1.544 (4)	C27—C277	1.537 (4)
C17—H17	1.0000	C27—H27	1.0000
C177—C171	1.507 (4)	C277—C271	1.507 (4)
C177—H17A	0.9900	C277—H27A	0.9900
C177—H17B	0.9900	C277—H27B	0.9900
C171—C172	1.376 (5)	C271—C276	1.379 (5)
C171—C176	1.395 (4)	C271—C272	1.388 (5)
C172—C173	1.391 (5)	C272—C273	1.390 (5)
C172—H172	0.9500	C272—H272	0.9500
C173—C174	1.377 (5)	C273—C274	1.374 (6)
C173—H173	0.9500	C273—H273	0.9500
C174—C175	1.378 (5)	C274—C275	1.383 (6)
C174—H174	0.9500	C274—H274	0.9500
C175—C176	1.385 (5)	C275—C276	1.380 (5)
C175—H175	0.9500	C275—H275	0.9500
C176—H176	0.9500	C276—H276	0.9500
C18—O181	1.189 (4)	C28—O281	1.191 (4)
C18—O182	1.321 (4)	C28—O282	1.313 (4)
O182—C19	1.466 (4)	O282—C29	1.458 (5)
C19—C110	1.474 (5)	C29—C210	1.460 (6)
C19—H19A	0.9900	C29—H29A	0.9900
C19—H19B	0.9900	C29—H29B	0.9900
C110—H11A	0.9800	C210—H21A	0.9800
C110—H11B	0.9800	C210—H21B	0.9800
C110—H11C	0.9800	C210—H21C	0.9800
C16—N11—C12	115.7 (2)	C26—N21—C22	116.0 (2)
N12—C12—N13	117.6 (3)	N22—C22—N23	117.4 (3)
N12—C12—N11	114.7 (3)	N22—C22—N21	115.4 (3)
N13—C12—N11	127.7 (3)	N23—C22—N21	127.2 (3)
C12—N12—H12A	120.7	C22—N22—H22A	122.6
C12—N12—H12B	118.1	C22—N22—H22B	120.5
H12A—N12—H12B	119.9	H22A—N22—H22B	113.9
C14—N13—C12	115.5 (2)	C24—N23—C22	115.8 (2)
N13—C14—N14	119.1 (3)	N23—C24—N24	118.9 (3)
N13—C14—C15	123.1 (2)	N23—C24—C25	122.5 (3)
N14—C14—C15	117.8 (2)	N24—C24—C25	118.6 (3)
C14—N14—C17	123.0 (2)	C24—N24—C27	122.3 (2)
C14—N14—H14	118.5	C24—N24—H24	118.8
C17—N14—H14	118.5	C27—N24—H24	118.8
N15—C15—C16	117.1 (3)	N25—C25—C24	128.6 (3)
N15—C15—C14	128.8 (2)	N25—C25—C26	117.0 (3)
C16—C15—C14	114.1 (2)	C24—C25—C26	114.3 (2)
O15—N15—C15	117.8 (2)	O25—N25—C25	117.7 (3)
N11—C16—O16	120.5 (3)	N21—C26—O26	121.3 (3)
N11—C16—C15	123.9 (3)	N21—C26—C25	123.1 (3)
O16—C16—C15	115.6 (2)	O26—C26—C25	115.5 (2)
C16—O16—C167	118.3 (2)	C26—O26—C267	118.8 (2)
O16—C167—C161	110.5 (2)	O26—C267—C261	109.2 (3)
O16—C167—H16A	109.5	O26—C267—H26A	109.8
C161—C167—H16A	109.5	C261—C267—H26A	109.8
O16—C167—H16B	109.5	O26—C267—H26B	109.8
C161—C167—H16B	109.5	C261—C267—H26B	109.8
H16A—C167—H16B	108.1	H26A—C267—H26B	108.3
C162—C161—C166	119.1 (3)	C262—C261—C266	118.8 (3)
C162—C161—C167	121.1 (3)	C262—C261—C267	121.7 (3)
C166—C161—C167	119.8 (3)	C266—C261—C267	119.5 (3)
C161—C162—C163	121.1 (3)	C261—C262—C263	118.8 (4)
C161—C162—H162	119.5	C261—C262—H262	120.6
C163—C162—H162	119.5	C263—C262—H262	120.6
C162—C163—C164	119.6 (3)	C264—C263—C262	121.1 (4)
C162—C163—H163	120.2	C264—C263—H263	119.5
C164—C163—H163	120.2	C262—C263—H263	119.5
C165—C164—C163	119.4 (3)	C265—C264—C263	119.3 (4)
C165—C164—H164	120.3	C265—C264—H264	120.3
C163—C164—H164	120.3	C263—C264—H264	120.3
C166—C165—C164	120.7 (3)	C264—C265—C266	120.4 (5)
C166—C165—H165	119.6	C264—C265—H265	119.8
C164—C165—H165	119.6	C266—C265—H265	119.8
C165—C166—C161	120.1 (3)	C265—C266—C261	121.7 (4)
C165—C166—H166	120.0	C265—C266—H266	119.2
C161—C166—H166	120.0	C261—C266—H266	119.2
N14—C17—C18	110.7 (2)	N24—C27—C28	110.0 (2)
N14—C17—C177	109.7 (2)	N24—C27—C277	108.6 (2)
C18—C17—C177	107.9 (2)	C28—C27—C277	110.2 (3)
N14—C17—H17	109.5	N24—C27—H27	109.3
C18—C17—H17	109.5	C28—C27—H27	109.3
C177—C17—H17	109.5	C277—C27—H27	109.3
C171—C177—C17	114.5 (2)	C271—C277—C27	112.6 (2)
C171—C177—H17A	108.6	C271—C277—H27A	109.1
C17—C177—H17A	108.6	C27—C277—H27A	109.1
C171—C177—H17B	108.6	C271—C277—H27B	109.1
C17—C177—H17B	108.6	C27—C277—H27B	109.1
H17A—C177—H17B	107.6	H27A—C277—H27B	107.8
C172—C171—C176	117.9 (3)	C276—C271—C272	118.6 (3)
C172—C171—C177	120.6 (3)	C276—C271—C277	120.3 (3)
C176—C171—C177	121.5 (3)	C272—C271—C277	121.0 (3)
C171—C172—C173	121.6 (3)	C271—C272—C273	120.1 (4)
C171—C172—H172	119.2	C271—C272—H272	119.9
C173—C172—H172	119.2	C273—C272—H272	119.9
C174—C173—C172	119.6 (3)	C274—C273—C272	120.5 (4)
C174—C173—H173	120.2	C274—C273—H273	119.7
C172—C173—H173	120.2	C272—C273—H273	119.7
C173—C174—C175	120.0 (3)	C273—C274—C275	119.5 (3)
C173—C174—H174	120.0	C273—C274—H274	120.2
C175—C174—H174	120.0	C275—C274—H274	120.2
C174—C175—C176	120.0 (3)	C276—C275—C274	119.8 (4)
C174—C175—H175	120.0	C276—C275—H275	120.1
C176—C175—H175	120.0	C274—C275—H275	120.1
C175—C176—C171	121.0 (3)	C271—C276—C275	121.3 (3)
C175—C176—H176	119.5	C271—C276—H276	119.3
C171—C176—H176	119.5	C275—C276—H276	119.3
O181—C18—O182	126.0 (3)	O281—C28—O282	124.8 (3)
O181—C18—C17	124.4 (3)	O281—C28—C27	123.6 (3)
O182—C18—C17	109.4 (3)	O282—C28—C27	111.6 (3)
C18—O182—C19	116.1 (2)	C28—O282—C29	117.4 (3)
O182—C19—C110	107.3 (3)	O282—C29—C210	111.2 (4)
O182—C19—H19A	110.3	O282—C29—H29A	109.4
C110—C19—H19A	110.3	C210—C29—H29A	109.4
O182—C19—H19B	110.3	O282—C29—H29B	109.4
C110—C19—H19B	110.3	C210—C29—H29B	109.4
H19A—C19—H19B	108.5	H29A—C29—H29B	108.0
C19—C110—H11A	109.5	C29—C210—H21A	109.5
C19—C110—H11B	109.5	C29—C210—H21B	109.5
H11A—C110—H11B	109.5	H21A—C210—H21B	109.5
C19—C110—H11C	109.5	C29—C210—H21C	109.5
H11A—C110—H11C	109.5	H21A—C210—H21C	109.5
H11B—C110—H11C	109.5	H21B—C210—H21C	109.5
C16—N11—C12—N12	−176.5 (3)	C26—N21—C22—N22	176.0 (3)
C16—N11—C12—N13	4.4 (4)	C26—N21—C22—N23	−7.2 (4)
N12—C12—N13—C14	176.4 (3)	N22—C22—N23—C24	−174.1 (3)
N11—C12—N13—C14	−4.5 (4)	N21—C22—N23—C24	9.1 (4)
C12—N13—C14—N14	−179.1 (3)	C22—N23—C24—N24	−179.2 (3)
C12—N13—C14—C15	1.3 (4)	C22—N23—C24—C25	−1.2 (4)
N13—C14—N14—C17	−6.3 (4)	N23—C24—N24—C27	7.8 (4)
C15—C14—N14—C17	173.3 (2)	C25—C24—N24—C27	−170.3 (3)
N13—C14—C15—N15	178.6 (3)	N23—C24—C25—N25	175.7 (3)
N14—C14—C15—N15	−0.9 (4)	N24—C24—C25—N25	−6.2 (5)
N13—C14—C15—C16	1.4 (4)	N23—C24—C25—C26	−7.0 (4)
N14—C14—C15—C16	−178.1 (2)	N24—C24—C25—C26	171.0 (3)
C16—C15—N15—O15	178.3 (2)	C24—C25—N25—O25	−1.6 (5)
C14—C15—N15—O15	1.2 (4)	C26—C25—N25—O25	−178.8 (3)
C12—N11—C16—O16	179.2 (3)	C22—N21—C26—O26	177.4 (3)
C12—N11—C16—C15	−1.0 (4)	C22—N21—C26—C25	−2.8 (4)
N15—C15—C16—N11	−179.1 (3)	N25—C25—C26—N21	−173.2 (3)
C14—C15—C16—N11	−1.6 (4)	C24—C25—C26—N21	9.2 (4)
N15—C15—C16—O16	0.7 (4)	N25—C25—C26—O26	6.6 (4)
C14—C15—C16—O16	178.2 (2)	C24—C25—C26—O26	−170.9 (3)
N11—C16—O16—C167	−3.7 (4)	N21—C26—O26—C267	0.9 (4)
C15—C16—O16—C167	176.5 (2)	C25—C26—O26—C267	−179.0 (3)
C16—O16—C167—C161	−84.4 (3)	C26—O26—C267—C261	116.3 (3)
O16—C167—C161—C162	94.5 (3)	O26—C267—C261—C262	−52.9 (4)
O16—C167—C161—C166	−85.6 (3)	O26—C267—C261—C266	128.6 (3)
C166—C161—C162—C163	−0.4 (5)	C266—C261—C262—C263	−0.9 (5)
C167—C161—C162—C163	179.6 (3)	C267—C261—C262—C263	−179.4 (3)
C161—C162—C163—C164	0.8 (6)	C261—C262—C263—C264	1.1 (6)
C162—C163—C164—C165	−0.5 (6)	C262—C263—C264—C265	−0.8 (7)
C163—C164—C165—C166	−0.1 (6)	C263—C264—C265—C266	0.3 (6)
C164—C165—C166—C161	0.5 (5)	C264—C265—C266—C261	−0.1 (6)
C162—C161—C166—C165	−0.3 (5)	C262—C261—C266—C265	0.4 (5)
C167—C161—C166—C165	179.7 (3)	C267—C261—C266—C265	179.0 (3)
C14—N14—C17—C18	−70.8 (4)	C24—N24—C27—C28	−76.9 (4)
C14—N14—C17—C177	170.2 (3)	C24—N24—C27—C277	162.4 (3)
N14—C17—C177—C171	−68.9 (3)	N24—C27—C277—C271	−171.6 (3)
C18—C17—C177—C171	170.4 (3)	C28—C27—C277—C271	67.8 (3)
C17—C177—C171—C172	−89.9 (3)	C27—C277—C271—C276	77.8 (4)
C17—C177—C171—C176	90.9 (4)	C27—C277—C271—C272	−101.8 (3)
C176—C171—C172—C173	−0.5 (5)	C276—C271—C272—C273	0.1 (5)
C177—C171—C172—C173	−179.7 (3)	C277—C271—C272—C273	179.8 (3)
C171—C172—C173—C174	0.5 (5)	C271—C272—C273—C274	−1.3 (5)
C172—C173—C174—C175	−0.3 (5)	C272—C273—C274—C275	1.5 (6)
C173—C174—C175—C176	0.0 (5)	C273—C274—C275—C276	−0.6 (5)
C174—C175—C176—C171	0.0 (5)	C272—C271—C276—C275	0.9 (5)
C172—C171—C176—C175	0.3 (4)	C277—C271—C276—C275	−178.8 (3)
C177—C171—C176—C175	179.5 (3)	C274—C275—C276—C271	−0.6 (5)
N14—C17—C18—O181	−17.0 (4)	N24—C27—C28—O281	−52.2 (4)
C177—C17—C18—O181	103.0 (3)	C277—C27—C28—O281	67.5 (4)
N14—C17—C18—O182	166.9 (2)	N24—C27—C28—O282	127.6 (3)
C177—C17—C18—O182	−73.1 (3)	C277—C27—C28—O282	−112.6 (3)
O181—C18—O182—C19	−2.3 (4)	O281—C28—O282—C29	4.6 (5)
C17—C18—O182—C19	173.8 (2)	C27—C28—O282—C29	−175.3 (3)
C18—O182—C19—C110	−173.0 (3)	C28—O282—C29—C210	−87.6 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N14—H14···O15	0.88	1.93	2.606 (3)	132
N24—H24···O25	0.88	1.96	2.621 (4)	131
N22—H22B···N15	0.88	2.48	3.302 (4)	155
N22—H22B···O16	0.88	2.44	3.115 (3)	133
N22—H22A···N25^i	0.88	2.22	2.925 (4)	137
N22—H22A···O25^i	0.88	2.17	3.043 (4)	167
N12—H12A···O15^ii	0.88	2.15	2.962 (4)	153
N12—H12B···O26^iii	0.88	2.46	3.199 (4)	142

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

(7) Ethyl N-(2-benzylamino-6-benzyloxy-5-nitrosopyrimidin-4-yl)-β-alaninate

Crystal data

C23H25N5O4	Z = 4
Mr = 435.48	F(000) = 920
Triclinic, P1	Dx = 1.342 Mg m^−3
a = 8.6595 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 16.3567 (4) Å	Cell parameters from 9402 reflections
c = 16.9014 (4) Å	θ = 1.3–27.5°
α = 105.2210 (13)°	µ = 0.09 mm^−1
β = 104.6960 (13)°	T = 150 K
γ = 100.3720 (12)°	Plate, pink
V = 2154.95 (9) Å^3	0.40 × 0.40 × 0.05 mm

Data collection

Kappa-CCD diffractometer	9402 independent reflections
Radiation source: fine-focus sealed X-ray tube	5874 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.092
φ scans, and ω scans with κ offsets	θmax = 27.5°, θmin = 1.3°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −11→11
Tmin = 0.963, Tmax = 0.995	k = −21→21
33749 measured reflections	l = −20→21

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.186	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.1133P)^2] where P = (Fo^2 + 2Fc^2)/3
9402 reflections	(Δ/σ)max < 0.001
579 parameters	Δρmax = 0.43 e Å^−3
0 restraints	Δρmin = −0.51 e Å^−3

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

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

	x	y	z	Uiso*/Ueq
N11	1.0249 (2)	0.60550 (11)	0.36876 (11)	0.0258 (4)
C12	1.0964 (3)	0.53673 (14)	0.35369 (14)	0.0237 (5)
C110	0.9030 (3)	0.05529 (15)	0.06382 (17)	0.0368 (6)
C111	0.7752 (3)	−0.00845 (16)	0.07868 (18)	0.0444 (7)
C121	1.1768 (3)	0.36350 (15)	0.38856 (14)	0.0260 (5)
C122	1.2141 (3)	0.29965 (16)	0.32948 (15)	0.0326 (6)
C123	1.1232 (3)	0.21208 (16)	0.30233 (16)	0.0392 (6)
C124	0.9959 (3)	0.18862 (16)	0.33340 (16)	0.0388 (6)
C125	0.9584 (3)	0.25153 (17)	0.39191 (17)	0.0387 (6)
C126	1.0498 (3)	0.33901 (16)	0.41971 (15)	0.0321 (6)
C127	1.2779 (3)	0.45847 (14)	0.42033 (14)	0.0275 (5)
N12	1.1799 (2)	0.52204 (12)	0.42361 (11)	0.0262 (4)
N13	1.0906 (2)	0.48350 (12)	0.27675 (11)	0.0246 (4)
N14	0.9987 (2)	0.44785 (12)	0.12929 (12)	0.0270 (4)
C14	1.0081 (3)	0.49941 (14)	0.20697 (14)	0.0237 (5)
C15	0.9297 (3)	0.57093 (14)	0.21315 (14)	0.0243 (5)
N15	0.8397 (2)	0.59235 (12)	0.14840 (12)	0.0315 (5)
O15	0.8223 (2)	0.54515 (11)	0.07058 (10)	0.0364 (4)
C16	0.9478 (3)	0.62152 (14)	0.30028 (14)	0.0254 (5)
C161	0.8292 (3)	0.82000 (15)	0.38664 (15)	0.0300 (5)
C162	0.8311 (4)	0.87995 (19)	0.46225 (18)	0.0534 (8)
C163	0.7762 (4)	0.9539 (2)	0.4606 (2)	0.0643 (10)
C164	0.7198 (4)	0.96951 (17)	0.38387 (18)	0.0444 (7)
C165	0.7148 (3)	0.91037 (16)	0.30858 (17)	0.0381 (6)
C166	0.7697 (3)	0.83533 (16)	0.30975 (16)	0.0344 (6)
C167	0.8931 (3)	0.74143 (15)	0.39275 (15)	0.0308 (5)
O16	0.8797 (2)	0.68909 (10)	0.30716 (10)	0.0305 (4)
C17	1.0632 (3)	0.37082 (14)	0.11721 (15)	0.0273 (5)
C18	0.9430 (3)	0.29325 (14)	0.12118 (14)	0.0260 (5)
C19	0.9878 (3)	0.20869 (15)	0.09095 (14)	0.0278 (5)
O191	1.1054 (2)	0.20011 (11)	0.06813 (12)	0.0414 (5)
O192	0.8746 (2)	0.14106 (10)	0.09233 (10)	0.0328 (4)
N21	0.5303 (2)	0.52903 (11)	−0.15940 (11)	0.0249 (4)
C22	0.5347 (3)	0.60947 (14)	−0.10538 (14)	0.0236 (5)
C210	0.7199 (3)	0.99200 (19)	−0.29453 (19)	0.0487 (7)
C211	0.8936 (3)	1.0462 (2)	−0.2688 (2)	0.0531 (8)
C221	0.4696 (3)	0.72026 (14)	0.06291 (13)	0.0269 (5)
C222	0.4357 (3)	0.80224 (15)	0.07891 (15)	0.0320 (6)
C223	0.2947 (3)	0.81434 (17)	0.09916 (16)	0.0387 (6)
C224	0.1824 (3)	0.74482 (18)	0.10318 (15)	0.0386 (6)
C225	0.2154 (3)	0.66285 (17)	0.08679 (15)	0.0369 (6)
C226	0.3562 (3)	0.65088 (15)	0.06777 (14)	0.0317 (6)
C227	0.6261 (3)	0.70802 (14)	0.04390 (14)	0.0282 (5)
N22	0.6036 (2)	0.62425 (12)	−0.02172 (12)	0.0286 (4)
N23	0.4804 (2)	0.67442 (11)	−0.12799 (11)	0.0245 (4)
C24	0.4181 (3)	0.66066 (14)	−0.21238 (14)	0.0232 (5)
N24	0.3715 (2)	0.72597 (11)	−0.23708 (12)	0.0261 (4)
C25	0.4026 (3)	0.57868 (14)	−0.27663 (13)	0.0235 (5)
N25	0.3449 (2)	0.55658 (12)	−0.36322 (12)	0.0297 (5)
O25	0.2950 (2)	0.61498 (11)	−0.39373 (10)	0.0352 (4)
C26	0.4659 (3)	0.51608 (14)	−0.24142 (14)	0.0241 (5)
C261	0.5591 (3)	0.31559 (14)	−0.34602 (14)	0.0257 (5)
C262	0.6313 (3)	0.24916 (15)	−0.33096 (15)	0.0341 (6)
C263	0.6552 (3)	0.18896 (17)	−0.39780 (17)	0.0402 (6)
C264	0.6095 (3)	0.19365 (17)	−0.48069 (16)	0.0385 (6)
C265	0.5379 (3)	0.25925 (16)	−0.49580 (15)	0.0346 (6)
C266	0.5124 (3)	0.31946 (15)	−0.42890 (15)	0.0306 (5)
C267	0.5375 (3)	0.37955 (14)	−0.26986 (15)	0.0291 (5)
O26	0.46020 (19)	0.44173 (9)	−0.30050 (9)	0.0292 (4)
C27	0.3916 (3)	0.81161 (14)	−0.17607 (14)	0.0263 (5)
C28	0.5539 (3)	0.87639 (15)	−0.16100 (14)	0.0302 (5)
C29	0.5584 (3)	0.90424 (14)	−0.23811 (15)	0.0296 (5)
O291	0.4459 (2)	0.88055 (12)	−0.30486 (11)	0.0455 (5)
O292	0.7037 (2)	0.96039 (11)	−0.22346 (11)	0.0360 (4)
H11A	1.0154	0.0558	0.0970	0.044*
H11B	0.8932	0.0385	0.0017	0.044*
H11C	0.7896	0.0072	0.1407	0.067*
H11D	0.7876	−0.0679	0.0574	0.067*
H11E	0.6645	−0.0064	0.0477	0.067*
H122	1.3016	0.3156	0.3075	0.039*
H123	1.1495	0.1685	0.2622	0.047*
H124	0.9339	0.1290	0.3145	0.047*
H125	0.8703	0.2354	0.4134	0.046*
H126	1.0241	0.3821	0.4606	0.038*
H12A	1.3556	0.4713	0.4790	0.033*
H12B	1.3447	0.4660	0.3819	0.033*
H12	1.1758	0.5520	0.4742	0.031*
H14	0.9515	0.4610	0.0834	0.032*
H162	0.8706	0.8701	0.5158	0.064*
H163	0.7775	0.9942	0.5129	0.077*
H164	0.6844	1.0211	0.3831	0.053*
H165	0.6737	0.9203	0.2552	0.046*
H166	0.7660	0.7946	0.2571	0.041*
H16A	1.0101	0.7608	0.4301	0.037*
H16B	0.8274	0.7063	0.4184	0.037*
H17A	1.1705	0.3842	0.1628	0.033*
H17B	1.0824	0.3556	0.0605	0.033*
H18A	0.9419	0.3039	0.1814	0.031*
H18B	0.8301	0.2881	0.0847	0.031*
H21A	0.6413	1.0279	−0.3059	0.058*
H21B	0.6954	0.9419	−0.3477	0.058*
H21C	0.9166	1.0953	−0.2158	0.080*
H21D	0.9084	1.0691	−0.3152	0.080*
H21E	0.9700	1.0098	−0.2585	0.080*
H222	0.5108	0.8505	0.0758	0.038*
H223	0.2746	0.8708	0.1104	0.046*
H224	0.0851	0.7529	0.1168	0.046*
H225	0.1392	0.6144	0.0888	0.044*
H226	0.3769	0.5945	0.0577	0.038*
H22A	0.6702	0.7565	0.0242	0.034*
H22B	0.7096	0.7120	0.0980	0.034*
H22	0.6372	0.5821	−0.0049	0.034*
H24	0.3266	0.7168	−0.2926	0.031*
H262	0.6642	0.2454	−0.2742	0.041*
H263	0.7036	0.1437	−0.3868	0.048*
H264	0.6271	0.1523	−0.5265	0.046*
H265	0.5058	0.2631	−0.5525	0.042*
H266	0.4620	0.3640	−0.4403	0.037*
H26A	0.4670	0.3478	−0.2437	0.035*
H26B	0.6464	0.4107	−0.2254	0.035*
H27A	0.3868	0.8046	−0.1203	0.032*
H27B	0.2987	0.8356	−0.1983	0.032*
H28A	0.5714	0.9290	−0.1112	0.036*
H28B	0.6458	0.8491	−0.1461	0.036*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0282 (10)	0.0186 (10)	0.0270 (10)	0.0062 (8)	0.0048 (8)	0.0054 (8)
C12	0.0226 (11)	0.0205 (11)	0.0246 (12)	0.0014 (9)	0.0044 (9)	0.0078 (9)
C110	0.0443 (15)	0.0201 (13)	0.0434 (15)	0.0132 (11)	0.0139 (12)	0.0031 (11)
C111	0.0517 (17)	0.0235 (13)	0.0504 (17)	0.0066 (12)	0.0104 (14)	0.0077 (12)
C121	0.0265 (12)	0.0255 (12)	0.0227 (12)	0.0088 (10)	0.0000 (9)	0.0085 (9)
C122	0.0350 (14)	0.0304 (13)	0.0316 (13)	0.0121 (11)	0.0098 (11)	0.0072 (11)
C123	0.0499 (16)	0.0274 (13)	0.0313 (14)	0.0153 (12)	0.0018 (12)	0.0024 (11)
C124	0.0383 (15)	0.0259 (13)	0.0411 (15)	0.0031 (11)	−0.0037 (12)	0.0123 (12)
C125	0.0342 (14)	0.0385 (15)	0.0420 (15)	0.0049 (12)	0.0073 (12)	0.0183 (13)
C126	0.0342 (13)	0.0323 (13)	0.0287 (13)	0.0103 (11)	0.0073 (11)	0.0098 (11)
C127	0.0270 (12)	0.0249 (12)	0.0251 (12)	0.0069 (10)	0.0016 (10)	0.0056 (10)
N12	0.0320 (10)	0.0242 (10)	0.0200 (10)	0.0101 (9)	0.0048 (8)	0.0048 (8)
N13	0.0270 (10)	0.0197 (9)	0.0217 (10)	0.0041 (8)	0.0023 (8)	0.0046 (8)
N14	0.0330 (11)	0.0208 (10)	0.0211 (10)	0.0052 (8)	0.0015 (8)	0.0053 (8)
C14	0.0231 (11)	0.0192 (11)	0.0236 (12)	0.0010 (9)	0.0030 (9)	0.0058 (9)
C15	0.0254 (11)	0.0173 (11)	0.0259 (12)	0.0028 (9)	0.0039 (10)	0.0060 (9)
N15	0.0362 (11)	0.0233 (10)	0.0287 (11)	0.0051 (9)	0.0022 (9)	0.0077 (9)
O15	0.0478 (11)	0.0284 (9)	0.0269 (9)	0.0113 (8)	0.0021 (8)	0.0075 (7)
C16	0.0231 (11)	0.0170 (11)	0.0311 (13)	0.0024 (9)	0.0042 (10)	0.0059 (9)
C161	0.0290 (12)	0.0240 (12)	0.0321 (13)	0.0056 (10)	0.0048 (10)	0.0066 (10)
C162	0.084 (2)	0.0459 (17)	0.0301 (15)	0.0381 (17)	0.0083 (14)	0.0076 (13)
C163	0.099 (3)	0.0473 (19)	0.0444 (18)	0.0448 (19)	0.0145 (17)	0.0029 (14)
C164	0.0517 (17)	0.0290 (14)	0.0517 (17)	0.0195 (13)	0.0100 (14)	0.0117 (13)
C165	0.0433 (15)	0.0298 (14)	0.0424 (15)	0.0106 (12)	0.0099 (12)	0.0164 (12)
C166	0.0409 (14)	0.0244 (13)	0.0365 (14)	0.0083 (11)	0.0121 (12)	0.0077 (11)
C167	0.0362 (13)	0.0250 (12)	0.0284 (13)	0.0118 (11)	0.0060 (10)	0.0056 (10)
O16	0.0361 (9)	0.0207 (8)	0.0307 (9)	0.0129 (7)	0.0046 (7)	0.0041 (7)
C17	0.0285 (12)	0.0233 (12)	0.0256 (12)	0.0072 (10)	0.0055 (10)	0.0035 (9)
C18	0.0251 (12)	0.0221 (12)	0.0265 (12)	0.0065 (10)	0.0044 (10)	0.0043 (9)
C19	0.0281 (12)	0.0262 (13)	0.0267 (12)	0.0077 (10)	0.0055 (10)	0.0071 (10)
O191	0.0397 (11)	0.0324 (10)	0.0597 (12)	0.0159 (9)	0.0249 (9)	0.0141 (9)
O192	0.0383 (9)	0.0176 (8)	0.0425 (10)	0.0088 (7)	0.0170 (8)	0.0050 (7)
N21	0.0294 (10)	0.0186 (10)	0.0238 (10)	0.0048 (8)	0.0070 (8)	0.0045 (8)
C22	0.0253 (12)	0.0213 (11)	0.0215 (12)	0.0030 (9)	0.0053 (9)	0.0068 (9)
C210	0.0467 (17)	0.0489 (17)	0.0573 (18)	0.0061 (14)	0.0154 (14)	0.0334 (15)
C211	0.0438 (17)	0.0467 (18)	0.072 (2)	0.0044 (14)	0.0190 (15)	0.0288 (16)
C221	0.0347 (13)	0.0221 (12)	0.0155 (11)	0.0040 (10)	−0.0009 (9)	0.0032 (9)
C222	0.0392 (14)	0.0187 (12)	0.0305 (13)	0.0059 (10)	0.0031 (11)	0.0045 (10)
C223	0.0468 (16)	0.0302 (14)	0.0325 (14)	0.0160 (12)	0.0046 (12)	0.0031 (11)
C224	0.0362 (14)	0.0483 (17)	0.0273 (13)	0.0142 (13)	0.0070 (11)	0.0065 (12)
C225	0.0414 (15)	0.0369 (15)	0.0258 (13)	0.0025 (12)	0.0072 (11)	0.0081 (11)
C226	0.0435 (15)	0.0212 (12)	0.0253 (12)	0.0050 (11)	0.0061 (11)	0.0064 (10)
C227	0.0336 (13)	0.0205 (11)	0.0209 (11)	0.0052 (10)	0.0006 (10)	0.0003 (9)
N22	0.0375 (11)	0.0226 (10)	0.0232 (10)	0.0099 (9)	0.0046 (9)	0.0069 (8)
N23	0.0296 (10)	0.0192 (9)	0.0229 (10)	0.0061 (8)	0.0050 (8)	0.0073 (8)
C24	0.0243 (11)	0.0206 (11)	0.0228 (12)	0.0049 (9)	0.0057 (9)	0.0066 (9)
N24	0.0353 (11)	0.0205 (10)	0.0204 (10)	0.0087 (8)	0.0044 (8)	0.0066 (8)
C25	0.0269 (12)	0.0186 (11)	0.0215 (11)	0.0044 (9)	0.0047 (9)	0.0045 (9)
N25	0.0345 (11)	0.0271 (11)	0.0259 (11)	0.0083 (9)	0.0066 (9)	0.0086 (8)
O25	0.0498 (11)	0.0297 (9)	0.0253 (9)	0.0170 (8)	0.0054 (8)	0.0095 (7)
C26	0.0255 (12)	0.0178 (11)	0.0251 (12)	0.0017 (9)	0.0061 (10)	0.0050 (9)
C261	0.0278 (12)	0.0180 (11)	0.0260 (12)	0.0013 (9)	0.0052 (10)	0.0052 (9)
C262	0.0500 (16)	0.0255 (13)	0.0274 (13)	0.0147 (12)	0.0094 (11)	0.0092 (10)
C263	0.0547 (17)	0.0297 (14)	0.0386 (15)	0.0209 (13)	0.0125 (13)	0.0108 (11)
C264	0.0512 (16)	0.0289 (14)	0.0327 (14)	0.0114 (12)	0.0157 (12)	0.0030 (11)
C265	0.0460 (15)	0.0301 (13)	0.0256 (13)	0.0078 (12)	0.0095 (11)	0.0087 (10)
C266	0.0386 (14)	0.0216 (12)	0.0277 (13)	0.0074 (10)	0.0062 (10)	0.0062 (10)
C267	0.0374 (13)	0.0196 (11)	0.0290 (12)	0.0091 (10)	0.0061 (10)	0.0090 (10)
O26	0.0380 (9)	0.0181 (8)	0.0256 (8)	0.0083 (7)	0.0037 (7)	0.0031 (7)
C27	0.0332 (13)	0.0229 (12)	0.0239 (12)	0.0115 (10)	0.0099 (10)	0.0061 (9)
C28	0.0328 (13)	0.0241 (12)	0.0283 (13)	0.0073 (10)	0.0042 (10)	0.0053 (10)
C29	0.0310 (13)	0.0194 (12)	0.0377 (14)	0.0074 (10)	0.0104 (11)	0.0081 (10)
O291	0.0415 (11)	0.0499 (12)	0.0351 (10)	−0.0038 (9)	−0.0016 (9)	0.0217 (9)
O292	0.0341 (9)	0.0283 (9)	0.0422 (10)	0.0020 (8)	0.0085 (8)	0.0132 (8)

Geometric parameters (Å, º)

N11—C16	1.298 (3)	N21—C26	1.299 (3)
N11—C12	1.376 (3)	N21—C22	1.378 (3)
C12—N12	1.325 (3)	C22—N22	1.324 (3)
C12—N13	1.345 (3)	C22—N23	1.341 (3)
C110—O192	1.446 (3)	C210—O292	1.454 (3)
C110—C111	1.496 (4)	C210—C211	1.491 (4)
C110—H11A	0.9900	C210—H21A	0.9900
C110—H11B	0.9900	C210—H21B	0.9900
C111—H11C	0.9800	C211—H21C	0.9800
C111—H11D	0.9800	C211—H21D	0.9800
C111—H11E	0.9800	C211—H21E	0.9800
C121—C126	1.376 (3)	C221—C226	1.396 (3)
C121—C122	1.389 (3)	C221—C222	1.396 (3)
C121—C127	1.517 (3)	C221—C227	1.505 (3)
C122—C123	1.396 (3)	C222—C223	1.383 (4)
C122—H122	0.9500	C222—H222	0.9500
C123—C124	1.372 (4)	C223—C224	1.385 (4)
C123—H123	0.9500	C223—H223	0.9500
C124—C125	1.375 (4)	C224—C225	1.393 (4)
C124—H124	0.9500	C224—H224	0.9500
C125—C126	1.395 (3)	C225—C226	1.371 (4)
C125—H125	0.9500	C225—H225	0.9500
C126—H126	0.9500	C226—H226	0.9500
C127—N12	1.455 (3)	C227—N22	1.463 (3)
C127—H12A	0.9900	C227—H22A	0.9900
C127—H12B	0.9900	C227—H22B	0.9900
N12—H12	0.8800	N22—H22	0.8800
N13—C14	1.330 (3)	N23—C24	1.332 (3)
N14—C14	1.335 (3)	C24—N24	1.335 (3)
N14—C17	1.455 (3)	C24—C25	1.446 (3)
N14—H14	0.8800	N24—C27	1.456 (3)
C14—C15	1.448 (3)	N24—H24	0.8800
C15—N15	1.340 (3)	C25—N25	1.345 (3)
C15—C16	1.440 (3)	C25—C26	1.435 (3)
N15—O15	1.294 (2)	N25—O25	1.288 (2)
C16—O16	1.336 (3)	C26—O26	1.339 (3)
C161—C166	1.377 (3)	C261—C266	1.378 (3)
C161—C162	1.386 (4)	C261—C262	1.395 (3)
C161—C167	1.505 (3)	C261—C267	1.507 (3)
C162—C163	1.381 (4)	C262—C263	1.377 (3)
C162—H162	0.9500	C262—H262	0.9500
C163—C164	1.372 (4)	C263—C264	1.382 (3)
C163—H163	0.9500	C263—H263	0.9500
C164—C165	1.367 (4)	C264—C265	1.380 (3)
C164—H164	0.9500	C264—H264	0.9500
C165—C166	1.397 (3)	C265—C266	1.385 (3)
C165—H165	0.9500	C265—H265	0.9500
C166—H166	0.9500	C266—H266	0.9500
C167—O16	1.438 (3)	C267—O26	1.448 (2)
C167—H16A	0.9900	C267—H26A	0.9900
C167—H16B	0.9900	C267—H26B	0.9900
C17—C18	1.517 (3)	C27—C28	1.518 (3)
C17—H17A	0.9900	C27—H27A	0.9900
C17—H17B	0.9900	C27—H27B	0.9900
C18—C19	1.499 (3)	C28—C29	1.496 (3)
C18—H18A	0.9900	C28—H28A	0.9900
C18—H18B	0.9900	C28—H28B	0.9900
C19—O191	1.195 (3)	C29—O291	1.204 (3)
C19—O192	1.349 (3)	C29—O292	1.340 (3)
C16—N11—C12	115.32 (19)	C26—N21—C22	115.11 (18)
N12—C12—N13	117.10 (19)	N22—C22—N23	116.8 (2)
N12—C12—N11	115.47 (19)	N22—C22—N21	115.66 (19)
N13—C12—N11	127.44 (19)	N23—C22—N21	127.50 (19)
O192—C110—C111	107.4 (2)	O292—C210—C211	107.4 (2)
O192—C110—H11A	110.2	O292—C210—H21A	110.2
C111—C110—H11A	110.2	C211—C210—H21A	110.2
O192—C110—H11B	110.2	O292—C210—H21B	110.2
C111—C110—H11B	110.2	C211—C210—H21B	110.2
H11A—C110—H11B	108.5	H21A—C210—H21B	108.5
C110—C111—H11C	109.5	C210—C211—H21C	109.5
C110—C111—H11D	109.5	C210—C211—H21D	109.5
H11C—C111—H11D	109.5	H21C—C211—H21D	109.5
C110—C111—H11E	109.5	C210—C211—H21E	109.5
H11C—C111—H11E	109.5	H21C—C211—H21E	109.5
H11D—C111—H11E	109.5	H21D—C211—H21E	109.5
C126—C121—C122	119.1 (2)	C226—C221—C222	117.8 (2)
C126—C121—C127	120.4 (2)	C226—C221—C227	121.2 (2)
C122—C121—C127	120.5 (2)	C222—C221—C227	120.9 (2)
C121—C122—C123	120.1 (2)	C223—C222—C221	121.1 (2)
C121—C122—H122	119.9	C223—C222—H222	119.5
C123—C122—H122	119.9	C221—C222—H222	119.5
C124—C123—C122	120.3 (2)	C222—C223—C224	120.6 (2)
C124—C123—H123	119.9	C222—C223—H223	119.7
C122—C123—H123	119.9	C224—C223—H223	119.7
C123—C124—C125	119.9 (2)	C223—C224—C225	118.5 (2)
C123—C124—H124	120.0	C223—C224—H224	120.8
C125—C124—H124	120.0	C225—C224—H224	120.8
C124—C125—C126	120.0 (2)	C226—C225—C224	121.1 (2)
C124—C125—H125	120.0	C226—C225—H225	119.4
C126—C125—H125	120.0	C224—C225—H225	119.4
C121—C126—C125	120.7 (2)	C225—C226—C221	120.9 (2)
C121—C126—H126	119.7	C225—C226—H226	119.5
C125—C126—H126	119.7	C221—C226—H226	119.5
N12—C127—C121	114.33 (18)	N22—C227—C221	113.71 (18)
N12—C127—H12A	108.7	N22—C227—H22A	108.8
C121—C127—H12A	108.7	C221—C227—H22A	108.8
N12—C127—H12B	108.7	N22—C227—H22B	108.8
C121—C127—H12B	108.7	C221—C227—H22B	108.8
H12A—C127—H12B	107.6	H22A—C227—H22B	107.7
C12—N12—C127	122.82 (19)	C22—N22—C227	122.56 (18)
C12—N12—H12	118.6	C22—N22—H22	118.7
C127—N12—H12	118.6	C227—N22—H22	118.7
C14—N13—C12	116.64 (19)	C24—N23—C22	116.49 (19)
C14—N14—C17	122.87 (18)	N23—C24—N24	117.91 (19)
C14—N14—H14	118.6	N23—C24—C25	122.12 (19)
C17—N14—H14	118.6	N24—C24—C25	119.96 (19)
N13—C14—N14	118.5 (2)	C24—N24—C27	122.78 (18)
N13—C14—C15	121.9 (2)	C24—N24—H24	118.6
N14—C14—C15	119.51 (19)	C27—N24—H24	118.6
N15—C15—C16	117.8 (2)	N25—C25—C26	117.43 (19)
N15—C15—C14	127.8 (2)	N25—C25—C24	128.32 (19)
C16—C15—C14	114.30 (18)	C26—C25—C24	114.16 (18)
O15—N15—C15	116.92 (19)	O25—N25—C25	116.58 (19)
N11—C16—O16	120.7 (2)	N21—C26—O26	120.71 (19)
N11—C16—C15	124.3 (2)	N21—C26—C25	124.6 (2)
O16—C16—C15	115.01 (18)	O26—C26—C25	114.68 (18)
C166—C161—C162	118.5 (2)	C266—C261—C262	118.6 (2)
C166—C161—C167	123.2 (2)	C266—C261—C267	123.7 (2)
C162—C161—C167	118.3 (2)	C262—C261—C267	117.6 (2)
C163—C162—C161	120.7 (3)	C263—C262—C261	120.4 (2)
C163—C162—H162	119.6	C263—C262—H262	119.8
C161—C162—H162	119.6	C261—C262—H262	119.8
C164—C163—C162	120.4 (3)	C262—C263—C264	120.7 (2)
C164—C163—H163	119.8	C262—C263—H263	119.6
C162—C163—H163	119.8	C264—C263—H263	119.6
C165—C164—C163	119.6 (2)	C265—C264—C263	119.0 (2)
C165—C164—H164	120.2	C265—C264—H264	120.5
C163—C164—H164	120.2	C263—C264—H264	120.5
C164—C165—C166	120.3 (2)	C264—C265—C266	120.5 (2)
C164—C165—H165	119.8	C264—C265—H265	119.8
C166—C165—H165	119.8	C266—C265—H265	119.8
C161—C166—C165	120.5 (2)	C261—C266—C265	120.8 (2)
C161—C166—H166	119.8	C261—C266—H266	119.6
C165—C166—H166	119.8	C265—C266—H266	119.6
O16—C167—C161	108.49 (18)	O26—C267—C261	108.03 (17)
O16—C167—H16A	110.0	O26—C267—H26A	110.1
C161—C167—H16A	110.0	C261—C267—H26A	110.1
O16—C167—H16B	110.0	O26—C267—H26B	110.1
C161—C167—H16B	110.0	C261—C267—H26B	110.1
H16A—C167—H16B	108.4	H26A—C267—H26B	108.4
C16—O16—C167	117.30 (17)	C26—O26—C267	117.61 (17)
N14—C17—C18	110.87 (18)	N24—C27—C28	112.49 (19)
N14—C17—H17A	109.5	N24—C27—H27A	109.1
C18—C17—H17A	109.5	C28—C27—H27A	109.1
N14—C17—H17B	109.5	N24—C27—H27B	109.1
C18—C17—H17B	109.5	C28—C27—H27B	109.1
H17A—C17—H17B	108.1	H27A—C27—H27B	107.8
C19—C18—C17	112.19 (18)	C29—C28—C27	112.72 (19)
C19—C18—H18A	109.2	C29—C28—H28A	109.0
C17—C18—H18A	109.2	C27—C28—H28A	109.0
C19—C18—H18B	109.2	C29—C28—H28B	109.0
C17—C18—H18B	109.2	C27—C28—H28B	109.0
H18A—C18—H18B	107.9	H28A—C28—H28B	107.8
O191—C19—O192	123.4 (2)	O291—C29—O292	123.7 (2)
O191—C19—C18	126.3 (2)	O291—C29—C28	124.9 (2)
O192—C19—C18	110.31 (19)	O292—C29—C28	111.46 (19)
C19—O192—C110	115.80 (18)	C29—O292—C210	115.66 (19)
C16—N11—C12—N12	177.88 (19)	C26—N21—C22—N22	−178.46 (19)
C16—N11—C12—N13	−2.2 (3)	C26—N21—C22—N23	0.2 (3)
C126—C121—C122—C123	0.1 (3)	C226—C221—C222—C223	0.2 (3)
C127—C121—C122—C123	178.3 (2)	C227—C221—C222—C223	−177.9 (2)
C121—C122—C123—C124	0.4 (3)	C221—C222—C223—C224	−0.7 (4)
C122—C123—C124—C125	−0.4 (4)	C222—C223—C224—C225	0.3 (4)
C123—C124—C125—C126	−0.1 (4)	C223—C224—C225—C226	0.5 (4)
C122—C121—C126—C125	−0.6 (3)	C224—C225—C226—C221	−1.0 (3)
C127—C121—C126—C125	−178.8 (2)	C222—C221—C226—C225	0.6 (3)
C124—C125—C126—C121	0.6 (3)	C227—C221—C226—C225	178.7 (2)
C126—C121—C127—N12	−45.6 (3)	C226—C221—C227—N22	40.0 (3)
C122—C121—C127—N12	136.2 (2)	C222—C221—C227—N22	−142.0 (2)
N13—C12—N12—C127	6.9 (3)	N23—C22—N22—C227	−2.1 (3)
N11—C12—N12—C127	−173.18 (18)	N21—C22—N22—C227	176.67 (19)
C121—C127—N12—C12	−76.1 (3)	C221—C227—N22—C22	76.6 (3)
N12—C12—N13—C14	−179.26 (19)	N22—C22—N23—C24	177.04 (19)
N11—C12—N13—C14	0.9 (3)	N21—C22—N23—C24	−1.6 (3)
C12—N13—C14—N14	−179.72 (19)	C22—N23—C24—N24	−176.36 (19)
C12—N13—C14—C15	0.6 (3)	C22—N23—C24—C25	2.7 (3)
C17—N14—C14—N13	5.1 (3)	N23—C24—N24—C27	2.3 (3)
C17—N14—C14—C15	−175.26 (19)	C25—C24—N24—C27	−176.7 (2)
N13—C14—C15—N15	−177.9 (2)	N23—C24—C25—N25	−178.8 (2)
N14—C14—C15—N15	2.4 (3)	N24—C24—C25—N25	0.2 (4)
N13—C14—C15—C16	−0.6 (3)	N23—C24—C25—C26	−2.4 (3)
N14—C14—C15—C16	179.72 (19)	N24—C24—C25—C26	176.62 (19)
C16—C15—N15—O15	−178.75 (19)	C26—C25—N25—O25	−177.20 (19)
C14—C15—N15—O15	−1.5 (3)	C24—C25—N25—O25	−0.9 (3)
C12—N11—C16—O16	−177.08 (18)	C22—N21—C26—O26	177.54 (19)
C12—N11—C16—C15	2.1 (3)	C22—N21—C26—C25	0.1 (3)
N15—C15—C16—N11	176.7 (2)	N25—C25—C26—N21	177.8 (2)
C14—C15—C16—N11	−0.9 (3)	C24—C25—C26—N21	0.9 (3)
N15—C15—C16—O16	−4.0 (3)	N25—C25—C26—O26	0.2 (3)
C14—C15—C16—O16	178.38 (18)	C24—C25—C26—O26	−176.64 (18)
C166—C161—C162—C163	−0.7 (5)	C266—C261—C262—C263	0.1 (4)
C167—C161—C162—C163	179.1 (3)	C267—C261—C262—C263	−179.7 (2)
C161—C162—C163—C164	−0.4 (5)	C261—C262—C263—C264	0.5 (4)
C162—C163—C164—C165	1.4 (5)	C262—C263—C264—C265	−0.6 (4)
C163—C164—C165—C166	−1.3 (4)	C263—C264—C265—C266	0.0 (4)
C162—C161—C166—C165	0.9 (4)	C262—C261—C266—C265	−0.6 (4)
C167—C161—C166—C165	−178.9 (2)	C267—C261—C266—C265	179.1 (2)
C164—C165—C166—C161	0.1 (4)	C264—C265—C266—C261	0.6 (4)
C166—C161—C167—O16	−0.1 (3)	C266—C261—C267—O26	0.5 (3)
C162—C161—C167—O16	−179.8 (2)	C262—C261—C267—O26	−179.7 (2)
N11—C16—O16—C167	−1.2 (3)	N21—C26—O26—C267	−3.9 (3)
C15—C16—O16—C167	179.55 (19)	C25—C26—O26—C267	173.77 (18)
C161—C167—O16—C16	172.60 (18)	C261—C267—O26—C26	−164.12 (18)
C14—N14—C17—C18	80.2 (3)	C24—N24—C27—C28	92.3 (2)
N14—C17—C18—C19	168.10 (18)	N24—C27—C28—C29	69.8 (2)
C17—C18—C19—O191	2.1 (3)	C27—C28—C29—O291	1.7 (3)
C17—C18—C19—O192	−177.63 (17)	C27—C28—C29—O292	−179.13 (19)
O191—C19—O192—C110	−0.2 (3)	O291—C29—O292—C210	−0.3 (4)
C18—C19—O192—C110	179.51 (18)	C28—C29—O292—C210	−179.5 (2)
C111—C110—O192—C19	174.4 (2)	C211—C210—O292—C29	−174.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N14—H14···O15	0.88	1.94	2.605 (3)	131
N24—H24···O25	0.88	1.97	2.626 (2)	131
N22—H22···O15	0.88	2.07	2.853 (3)	148
N12—H12···O25^i	0.88	2.09	2.875 (2)	149

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

(8) 4-Benzylamino-2, 6-bis(benzyloxy)-5-nitrosopyrimidine

Crystal data

C25H22N4O3	F(000) = 896
Mr = 426.47	Dx = 1.356 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 14.6856 (5) Å	Cell parameters from 3748 reflections
b = 7.7726 (2) Å	θ = 1.0–27.5°
c = 18.5721 (8) Å	µ = 0.09 mm^−1
β = 99.8847 (13)°	T = 150 K
V = 2088.45 (13) Å^3	Block, blue
Z = 4	0.55 × 0.30 × 0.20 mm

Data collection

Kappa-CCD diffractometer	4516 independent reflections
Radiation source: fine-focus sealed X-ray tube	3296 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
φ scans, and ω scans with κ offsets	θmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −19→19
Tmin = 0.952, Tmax = 0.982	k = −10→10
12659 measured reflections	l = −23→24

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.131	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0762P)^2] where P = (Fo^2 + 2Fc^2)/3
4516 reflections	(Δ/σ)max < 0.001
289 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

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

	x	y	z	Uiso*/Ueq
N1	0.43514 (9)	0.16792 (15)	0.16313 (7)	0.0242 (3)
O1	0.31952 (7)	0.07676 (13)	0.21623 (5)	0.0261 (3)
C2	0.35082 (10)	0.09446 (18)	0.15333 (8)	0.0219 (3)
C27	0.22778 (11)	0.0022 (2)	0.21259 (8)	0.0261 (4)
C21	0.19932 (10)	0.03258 (18)	0.28516 (8)	0.0236 (3)
C22	0.12115 (11)	0.1294 (2)	0.29029 (8)	0.0281 (4)
C23	0.09477 (11)	0.1594 (2)	0.35703 (9)	0.0311 (4)
C24	0.14670 (12)	0.0927 (2)	0.42013 (9)	0.0312 (4)
C25	0.22444 (12)	−0.0032 (2)	0.41601 (9)	0.0313 (4)
C26	0.25072 (11)	−0.03397 (19)	0.34911 (8)	0.0266 (4)
N3	0.29821 (8)	0.04188 (15)	0.09267 (7)	0.0226 (3)
N4	0.28347 (9)	0.01416 (16)	−0.03202 (7)	0.0248 (3)
C47	0.19410 (10)	−0.07359 (19)	−0.03837 (9)	0.0264 (4)
C41	0.11406 (10)	0.04965 (18)	−0.05604 (8)	0.0238 (3)
C42	0.08642 (11)	0.14954 (19)	−0.00150 (9)	0.0277 (4)
C43	0.01281 (12)	0.2617 (2)	−0.01754 (10)	0.0349 (4)
C44	−0.03421 (12)	0.2755 (2)	−0.08847 (11)	0.0382 (4)
C45	−0.00747 (12)	0.1782 (2)	−0.14326 (10)	0.0372 (4)
C46	0.06618 (11)	0.0657 (2)	−0.12697 (9)	0.0300 (4)
C4	0.33259 (10)	0.06754 (18)	0.03050 (8)	0.0219 (3)
C5	0.42021 (10)	0.15134 (18)	0.03175 (8)	0.0228 (3)
N5	0.46003 (9)	0.19294 (17)	−0.02671 (7)	0.0296 (3)
O5	0.41633 (8)	0.15117 (15)	−0.08944 (6)	0.0349 (3)
C6	0.46822 (10)	0.19524 (18)	0.10270 (8)	0.0222 (3)
O6	0.55135 (7)	0.26660 (14)	0.10635 (6)	0.0272 (3)
C67	0.59712 (11)	0.3188 (2)	0.17874 (9)	0.0307 (4)
C61	0.69605 (10)	0.36092 (18)	0.17546 (8)	0.0237 (3)
C62	0.76445 (11)	0.2924 (2)	0.22820 (9)	0.0306 (4)
C63	0.85648 (12)	0.3358 (2)	0.23021 (9)	0.0339 (4)
C64	0.88094 (12)	0.4455 (2)	0.17856 (9)	0.0317 (4)
C65	0.81326 (12)	0.51391 (19)	0.12521 (9)	0.0299 (4)
C66	0.72119 (11)	0.47310 (19)	0.12385 (8)	0.0257 (4)
H27A	0.2294	−0.1227	0.2023	0.031*
H27B	0.1835	0.0575	0.1732	0.031*
H22	0.0853	0.1756	0.2472	0.034*
H23	0.0411	0.2257	0.3597	0.037*
H24	0.1287	0.1132	0.4662	0.037*
H25	0.2602	−0.0486	0.4593	0.038*
H26	0.3042	−0.1010	0.3468	0.032*
H4	0.3059	0.0325	−0.0723	0.030*
H47A	0.1904	−0.1330	0.0082	0.032*
H47B	0.1895	−0.1619	−0.0773	0.032*
H42	0.1185	0.1405	0.0473	0.033*
H43	−0.0055	0.3293	0.0201	0.042*
H44	−0.0851	0.3521	−0.0995	0.046*
H45	−0.0395	0.1884	−0.1921	0.045*
H46	0.0843	−0.0015	−0.1649	0.036*
H67A	0.5942	0.2245	0.2141	0.037*
H67B	0.5658	0.4208	0.1951	0.037*
H62	0.7482	0.2147	0.2634	0.037*
H63	0.9027	0.2897	0.2673	0.041*
H64	0.9440	0.4742	0.1795	0.038*
H65	0.8300	0.5892	0.0894	0.036*
H66	0.6750	0.5219	0.0875	0.031*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0204 (7)	0.0294 (7)	0.0230 (7)	−0.0011 (5)	0.0040 (5)	−0.0010 (5)
O1	0.0218 (6)	0.0356 (6)	0.0216 (6)	−0.0054 (4)	0.0057 (5)	0.0001 (4)
C2	0.0204 (8)	0.0230 (7)	0.0226 (8)	0.0020 (6)	0.0048 (6)	0.0014 (6)
C27	0.0217 (8)	0.0318 (8)	0.0249 (9)	−0.0061 (6)	0.0045 (6)	0.0005 (6)
C21	0.0238 (8)	0.0239 (7)	0.0235 (8)	−0.0067 (6)	0.0053 (6)	−0.0005 (6)
C22	0.0260 (9)	0.0327 (8)	0.0246 (8)	−0.0009 (7)	0.0018 (7)	0.0021 (6)
C23	0.0266 (9)	0.0359 (9)	0.0317 (9)	−0.0005 (7)	0.0074 (7)	−0.0041 (7)
C24	0.0343 (10)	0.0368 (9)	0.0242 (8)	−0.0073 (7)	0.0100 (7)	−0.0043 (7)
C25	0.0360 (10)	0.0331 (8)	0.0232 (9)	−0.0059 (7)	0.0001 (7)	0.0028 (6)
C26	0.0244 (8)	0.0259 (8)	0.0289 (9)	−0.0025 (6)	0.0031 (7)	0.0008 (6)
N3	0.0214 (7)	0.0248 (6)	0.0216 (7)	0.0003 (5)	0.0039 (5)	−0.0006 (5)
N4	0.0205 (7)	0.0321 (7)	0.0219 (7)	−0.0016 (5)	0.0039 (5)	−0.0032 (5)
C47	0.0252 (9)	0.0252 (8)	0.0280 (9)	−0.0027 (6)	0.0019 (7)	−0.0055 (6)
C41	0.0207 (8)	0.0237 (7)	0.0267 (8)	−0.0066 (6)	0.0031 (6)	0.0011 (6)
C42	0.0283 (9)	0.0266 (8)	0.0283 (9)	−0.0044 (7)	0.0050 (7)	−0.0003 (6)
C43	0.0329 (10)	0.0301 (8)	0.0442 (10)	−0.0004 (7)	0.0139 (8)	0.0003 (7)
C44	0.0240 (9)	0.0325 (9)	0.0578 (12)	0.0013 (7)	0.0061 (9)	0.0121 (8)
C45	0.0300 (10)	0.0398 (10)	0.0379 (10)	−0.0066 (8)	−0.0050 (8)	0.0092 (8)
C46	0.0281 (9)	0.0337 (8)	0.0268 (9)	−0.0061 (7)	0.0009 (7)	−0.0009 (7)
C4	0.0201 (8)	0.0218 (7)	0.0239 (8)	0.0044 (6)	0.0041 (6)	−0.0009 (6)
C5	0.0224 (8)	0.0246 (7)	0.0221 (8)	0.0028 (6)	0.0060 (6)	0.0002 (6)
N5	0.0302 (8)	0.0351 (7)	0.0235 (7)	0.0027 (6)	0.0043 (6)	0.0000 (6)
O5	0.0327 (7)	0.0474 (7)	0.0242 (6)	−0.0019 (5)	0.0042 (5)	0.0003 (5)
C6	0.0186 (8)	0.0224 (7)	0.0257 (8)	0.0010 (6)	0.0040 (6)	0.0011 (6)
O6	0.0205 (6)	0.0364 (6)	0.0245 (6)	−0.0054 (5)	0.0034 (5)	−0.0021 (4)
C67	0.0236 (9)	0.0439 (9)	0.0241 (8)	−0.0037 (7)	0.0029 (7)	−0.0048 (7)
C61	0.0216 (8)	0.0269 (7)	0.0228 (8)	−0.0028 (6)	0.0040 (6)	−0.0026 (6)
C62	0.0287 (9)	0.0348 (8)	0.0278 (9)	−0.0006 (7)	0.0035 (7)	0.0096 (7)
C63	0.0252 (9)	0.0428 (10)	0.0316 (9)	0.0026 (7)	−0.0014 (7)	0.0035 (7)
C64	0.0229 (9)	0.0396 (9)	0.0332 (9)	−0.0074 (7)	0.0065 (7)	−0.0067 (7)
C65	0.0378 (10)	0.0284 (8)	0.0249 (9)	−0.0106 (7)	0.0094 (7)	−0.0014 (6)
C66	0.0305 (9)	0.0245 (7)	0.0209 (8)	−0.0003 (6)	0.0006 (7)	−0.0007 (6)

Geometric parameters (Å, º)

N1—C6	1.3145 (18)	C42—H42	0.9500
N1—C2	1.3472 (19)	C43—C44	1.383 (3)
O1—C2	1.3339 (17)	C43—H43	0.9500
O1—C27	1.4575 (18)	C44—C45	1.378 (3)
C2—N3	1.3169 (19)	C44—H44	0.9500
C27—C21	1.497 (2)	C45—C46	1.383 (2)
C27—H27A	0.9900	C45—H45	0.9500
C27—H27B	0.9900	C46—H46	0.9500
C21—C22	1.389 (2)	C4—C5	1.439 (2)
C21—C26	1.393 (2)	C5—N5	1.3577 (19)
C22—C23	1.381 (2)	C5—C6	1.425 (2)
C22—H22	0.9500	N5—O5	1.2720 (16)
C23—C24	1.384 (2)	C6—O6	1.3321 (18)
C23—H23	0.9500	O6—C67	1.4537 (18)
C24—C25	1.377 (2)	C67—C61	1.501 (2)
C24—H24	0.9500	C67—H67A	0.9900
C25—C26	1.384 (2)	C67—H67B	0.9900
C25—H25	0.9500	C61—C62	1.384 (2)
C26—H26	0.9500	C61—C66	1.392 (2)
N3—C4	1.3522 (19)	C62—C63	1.387 (2)
N4—C4	1.3241 (19)	C62—H62	0.9500
N4—C47	1.4659 (19)	C63—C64	1.377 (2)
N4—H4	0.8800	C63—H63	0.9500
C47—C41	1.508 (2)	C64—C65	1.383 (2)
C47—H47A	0.9900	C64—H64	0.9500
C47—H47B	0.9900	C65—C66	1.385 (2)
C41—C46	1.388 (2)	C65—H65	0.9500
C41—C42	1.391 (2)	C66—H66	0.9500
C42—C43	1.381 (2)
C6—N1—C2	114.76 (12)	C42—C43—H43	120.0
C2—O1—C27	117.07 (11)	C44—C43—H43	120.0
N3—C2—O1	118.51 (13)	C45—C44—C43	120.15 (16)
N3—C2—N1	129.63 (14)	C45—C44—H44	119.9
O1—C2—N1	111.85 (12)	C43—C44—H44	119.9
O1—C27—C21	107.11 (12)	C44—C45—C46	119.78 (16)
O1—C27—H27A	110.3	C44—C45—H45	120.1
C21—C27—H27A	110.3	C46—C45—H45	120.1
O1—C27—H27B	110.3	C45—C46—C41	120.93 (16)
C21—C27—H27B	110.3	C45—C46—H46	119.5
H27A—C27—H27B	108.5	C41—C46—H46	119.5
C22—C21—C26	118.41 (14)	N4—C4—N3	118.39 (13)
C22—C21—C27	120.59 (13)	N4—C4—C5	120.47 (14)
C26—C21—C27	121.00 (14)	N3—C4—C5	121.13 (13)
C23—C22—C21	121.04 (14)	N5—C5—C6	118.02 (13)
C23—C22—H22	119.5	N5—C5—C4	126.99 (14)
C21—C22—H22	119.5	C6—C5—C4	114.99 (13)
C22—C23—C24	119.88 (15)	O5—N5—C5	116.93 (13)
C22—C23—H23	120.1	N1—C6—O6	119.58 (13)
C24—C23—H23	120.1	N1—C6—C5	123.65 (13)
C25—C24—C23	119.82 (15)	O6—C6—C5	116.77 (13)
C25—C24—H24	120.1	C6—O6—C67	115.94 (12)
C23—C24—H24	120.1	O6—C67—C61	108.70 (12)
C24—C25—C26	120.34 (15)	O6—C67—H67A	110.0
C24—C25—H25	119.8	C61—C67—H67A	110.0
C26—C25—H25	119.8	O6—C67—H67B	110.0
C25—C26—C21	120.52 (15)	C61—C67—H67B	110.0
C25—C26—H26	119.7	H67A—C67—H67B	108.3
C21—C26—H26	119.7	C62—C61—C66	118.85 (14)
C2—N3—C4	115.75 (12)	C62—C61—C67	118.52 (14)
C4—N4—C47	124.19 (13)	C66—C61—C67	122.54 (14)
C4—N4—H4	117.9	C61—C62—C63	120.73 (15)
C47—N4—H4	117.9	C61—C62—H62	119.6
N4—C47—C41	112.06 (12)	C63—C62—H62	119.6
N4—C47—H47A	109.2	C64—C63—C62	120.09 (15)
C41—C47—H47A	109.2	C64—C63—H63	120.0
N4—C47—H47B	109.2	C62—C63—H63	120.0
C41—C47—H47B	109.2	C63—C64—C65	119.73 (15)
H47A—C47—H47B	107.9	C63—C64—H64	120.1
C46—C41—C42	118.50 (15)	C65—C64—H64	120.1
C46—C41—C47	120.83 (14)	C64—C65—C66	120.27 (14)
C42—C41—C47	120.67 (14)	C64—C65—H65	119.9
C43—C42—C41	120.72 (15)	C66—C65—H65	119.9
C43—C42—H42	119.6	C65—C66—C61	120.31 (14)
C41—C42—H42	119.6	C65—C66—H66	119.8
C42—C43—C44	119.92 (17)	C61—C66—H66	119.8
C27—O1—C2—N3	−0.97 (19)	C47—N4—C4—C5	179.43 (13)
C27—O1—C2—N1	178.64 (12)	C2—N3—C4—N4	178.70 (12)
C6—N1—C2—N3	2.2 (2)	C2—N3—C4—C5	−1.55 (19)
C6—N1—C2—O1	−177.39 (12)	N4—C4—C5—N5	3.5 (2)
C2—O1—C27—C21	−167.21 (12)	N3—C4—C5—N5	−176.24 (13)
O1—C27—C21—C22	119.08 (15)	N4—C4—C5—C6	−177.16 (13)
O1—C27—C21—C26	−60.39 (17)	N3—C4—C5—C6	3.1 (2)
C26—C21—C22—C23	0.1 (2)	C6—C5—N5—O5	179.40 (12)
C27—C21—C22—C23	−179.42 (14)	C4—C5—N5—O5	−1.3 (2)
C21—C22—C23—C24	0.1 (2)	C2—N1—C6—O6	−179.67 (12)
C22—C23—C24—C25	0.0 (2)	C2—N1—C6—C5	−0.2 (2)
C23—C24—C25—C26	−0.2 (2)	N5—C5—C6—N1	177.20 (13)
C24—C25—C26—C21	0.4 (2)	C4—C5—C6—N1	−2.2 (2)
C22—C21—C26—C25	−0.3 (2)	N5—C5—C6—O6	−3.3 (2)
C27—C21—C26—C25	179.17 (13)	C4—C5—C6—O6	177.30 (12)
O1—C2—N3—C4	178.25 (12)	N1—C6—O6—C67	−3.61 (19)
N1—C2—N3—C4	−1.3 (2)	C5—C6—O6—C67	176.87 (13)
C4—N4—C47—C41	95.06 (16)	C6—O6—C67—C61	168.22 (12)
N4—C47—C41—C46	100.32 (16)	O6—C67—C61—C62	−132.15 (14)
N4—C47—C41—C42	−79.83 (18)	O6—C67—C61—C66	51.29 (19)
C46—C41—C42—C43	0.2 (2)	C66—C61—C62—C63	0.6 (2)
C47—C41—C42—C43	−179.63 (14)	C67—C61—C62—C63	−176.05 (15)
C41—C42—C43—C44	0.0 (2)	C61—C62—C63—C64	−1.3 (3)
C42—C43—C44—C45	−0.4 (3)	C62—C63—C64—C65	0.8 (3)
C43—C44—C45—C46	0.5 (3)	C63—C64—C65—C66	0.3 (2)
C44—C45—C46—C41	−0.3 (2)	C64—C65—C66—C61	−1.0 (2)
C42—C41—C46—C45	−0.1 (2)	C62—C61—C66—C65	0.5 (2)
C47—C41—C46—C45	179.76 (14)	C67—C61—C66—C65	177.04 (14)
C47—N4—C4—N3	−0.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O5	0.88	1.94	2.606 (2)	132
C23—H23···O5^i	0.95	2.40	3.304 (2)	159

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

(9) 2-Benzylamino-4,6-bis(benzyloxy)-5-nitrosopyrimidine

Crystal data

C25H22N4O3	F(000) = 896
Mr = 426.47	Dx = 1.320 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.8074 (3) Å	Cell parameters from 10763 reflections
b = 15.8175 (5) Å	θ = 1.0–27.5°
c = 10.2119 (5) Å	µ = 0.09 mm^−1
β = 105.7490 (11)°	T = 150 K
V = 2146.54 (13) Å^3	Prism, green
Z = 4	0.30 × 0.24 × 0.12 mm

Data collection

Kappa-CCD diffractometer	4857 independent reflections
Radiation source: fine-focus sealed X-ray tube	3078 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.075
φ scans, and ω scans with κ offsets	θmax = 27.5°, θmin = 1.5°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −17→17
Tmin = 0.974, Tmax = 0.989	k = −20→17
18529 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.126	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0662P)^2] where P = (Fo^2 + 2Fc^2)/3
4857 reflections	(Δ/σ)max < 0.001
289 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.34 e Å^−3

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

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

	x	y	z	Uiso*/Ueq
N1	0.50015 (9)	0.07931 (8)	0.71271 (13)	0.0292 (3)
C2	0.44359 (11)	0.04696 (10)	0.79069 (15)	0.0255 (4)
N2	0.44874 (9)	−0.03624 (8)	0.80871 (12)	0.0288 (3)
C27	0.39516 (12)	−0.08108 (10)	0.89206 (16)	0.0297 (4)
C21	0.28385 (12)	−0.09128 (9)	0.82721 (15)	0.0259 (4)
C22	0.24601 (12)	−0.10293 (10)	0.68817 (15)	0.0314 (4)
C23	0.14445 (13)	−0.11537 (11)	0.63036 (17)	0.0371 (4)
C24	0.07894 (13)	−0.11672 (11)	0.70990 (18)	0.0391 (4)
C25	0.11585 (14)	−0.10532 (12)	0.84851 (18)	0.0430 (5)
C26	0.21739 (13)	−0.09243 (11)	0.90681 (16)	0.0359 (4)
N3	0.38383 (9)	0.08991 (8)	0.85227 (12)	0.0260 (3)
C4	0.38463 (11)	0.17287 (10)	0.83976 (15)	0.0257 (4)
O4	0.32632 (8)	0.21897 (6)	0.89488 (11)	0.0307 (3)
C47	0.26184 (12)	0.17548 (10)	0.96309 (16)	0.0293 (4)
C41	0.20379 (11)	0.24149 (10)	1.01514 (14)	0.0274 (4)
C42	0.22755 (12)	0.32645 (10)	1.01768 (16)	0.0325 (4)
C43	0.17441 (13)	0.38493 (11)	1.07158 (17)	0.0383 (4)
C44	0.09707 (13)	0.35963 (12)	1.12310 (17)	0.0393 (4)
C45	0.07141 (14)	0.27519 (12)	1.11936 (18)	0.0429 (5)
C46	0.12455 (13)	0.21646 (11)	1.06500 (17)	0.0371 (4)
C5	0.44612 (11)	0.21630 (9)	0.77017 (16)	0.0269 (4)
N5	0.45786 (10)	0.30110 (8)	0.75387 (14)	0.0325 (3)
O5	0.41075 (9)	0.35166 (7)	0.80862 (12)	0.0390 (3)
C6	0.50100 (11)	0.16199 (10)	0.70490 (16)	0.0278 (4)
O6	0.55547 (8)	0.19977 (7)	0.63249 (11)	0.0348 (3)
C67	0.61012 (12)	0.14607 (11)	0.56116 (17)	0.0346 (4)
C61	0.70814 (12)	0.11442 (10)	0.65098 (15)	0.0302 (4)
C62	0.78388 (13)	0.17051 (11)	0.71259 (16)	0.0353 (4)
C63	0.87612 (14)	0.14156 (13)	0.78880 (17)	0.0422 (5)
C64	0.89430 (14)	0.05579 (13)	0.80209 (18)	0.0453 (5)
C65	0.81958 (15)	−0.00022 (12)	0.74110 (18)	0.0482 (5)
C66	0.72629 (14)	0.02845 (11)	0.66715 (17)	0.0386 (4)
H2	0.4864	−0.0657	0.7683	0.035*
H27A	0.4048	−0.0503	0.9791	0.036*
H27B	0.4255	−0.1379	0.9135	0.036*
H22	0.2906	−0.1023	0.6318	0.038*
H23	0.1198	−0.1230	0.5348	0.044*
H24	0.0090	−0.1254	0.6702	0.047*
H25	0.0710	−0.1063	0.9044	0.052*
H26	0.2417	−0.0843	1.0023	0.043*
H47A	0.3027	0.1413	1.0395	0.035*
H47B	0.2152	0.1373	0.8989	0.035*
H42	0.2808	0.3449	0.9821	0.039*
H43	0.1917	0.4431	1.0729	0.046*
H44	0.0614	0.4000	1.1611	0.047*
H45	0.0175	0.2572	1.1539	0.052*
H46	0.1063	0.1584	1.0620	0.045*
H67A	0.6234	0.1784	0.4848	0.042*
H67B	0.5674	0.0971	0.5222	0.042*
H62	0.7721	0.2296	0.7022	0.042*
H63	0.9271	0.1806	0.8321	0.051*
H64	0.9582	0.0356	0.8532	0.054*
H65	0.8322	−0.0593	0.7499	0.058*
H66	0.6746	−0.0108	0.6274	0.046*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0287 (8)	0.0237 (8)	0.0370 (8)	0.0000 (6)	0.0120 (6)	−0.0003 (6)
C2	0.0221 (8)	0.0230 (9)	0.0290 (8)	−0.0013 (7)	0.0032 (6)	−0.0029 (6)
N2	0.0304 (8)	0.0195 (7)	0.0390 (8)	0.0012 (6)	0.0138 (6)	−0.0018 (6)
C27	0.0331 (9)	0.0216 (9)	0.0337 (9)	0.0015 (7)	0.0079 (7)	0.0011 (7)
C21	0.0315 (9)	0.0160 (8)	0.0313 (8)	0.0012 (7)	0.0102 (7)	0.0002 (6)
C22	0.0343 (10)	0.0325 (10)	0.0301 (9)	−0.0023 (8)	0.0132 (7)	0.0002 (7)
C23	0.0393 (11)	0.0403 (11)	0.0287 (9)	−0.0045 (8)	0.0042 (7)	0.0031 (7)
C24	0.0299 (10)	0.0416 (11)	0.0438 (10)	−0.0016 (8)	0.0066 (8)	0.0026 (8)
C25	0.0384 (11)	0.0527 (13)	0.0439 (10)	0.0000 (9)	0.0212 (8)	−0.0019 (9)
C26	0.0381 (11)	0.0417 (11)	0.0297 (9)	−0.0020 (8)	0.0121 (7)	−0.0039 (7)
N3	0.0254 (7)	0.0190 (7)	0.0333 (7)	0.0008 (6)	0.0074 (5)	−0.0007 (5)
C4	0.0224 (8)	0.0233 (9)	0.0301 (8)	0.0025 (7)	0.0048 (6)	−0.0023 (6)
O4	0.0328 (7)	0.0220 (6)	0.0415 (7)	0.0006 (5)	0.0172 (5)	−0.0010 (5)
C47	0.0319 (9)	0.0254 (9)	0.0327 (9)	−0.0034 (7)	0.0122 (7)	0.0007 (7)
C41	0.0263 (9)	0.0298 (9)	0.0248 (8)	0.0023 (7)	0.0049 (6)	−0.0002 (7)
C42	0.0300 (10)	0.0298 (10)	0.0380 (9)	−0.0007 (7)	0.0100 (7)	−0.0032 (7)
C43	0.0391 (11)	0.0310 (10)	0.0428 (10)	0.0030 (8)	0.0079 (8)	−0.0061 (8)
C44	0.0386 (11)	0.0462 (12)	0.0331 (9)	0.0129 (9)	0.0097 (8)	−0.0045 (8)
C45	0.0408 (11)	0.0492 (13)	0.0453 (11)	0.0075 (9)	0.0227 (9)	0.0067 (9)
C46	0.0391 (11)	0.0333 (11)	0.0428 (10)	0.0020 (8)	0.0178 (8)	0.0056 (8)
C5	0.0242 (9)	0.0203 (9)	0.0354 (9)	0.0000 (7)	0.0066 (7)	0.0014 (6)
N5	0.0320 (8)	0.0230 (8)	0.0411 (8)	0.0007 (6)	0.0074 (6)	0.0001 (6)
O5	0.0427 (8)	0.0226 (7)	0.0525 (7)	0.0023 (6)	0.0143 (6)	−0.0017 (5)
C6	0.0237 (9)	0.0256 (9)	0.0338 (9)	−0.0009 (7)	0.0073 (7)	0.0022 (7)
O6	0.0343 (7)	0.0275 (7)	0.0484 (7)	0.0032 (5)	0.0209 (6)	0.0052 (5)
C67	0.0364 (10)	0.0355 (10)	0.0371 (9)	0.0027 (8)	0.0188 (8)	0.0005 (7)
C61	0.0360 (10)	0.0288 (10)	0.0313 (9)	0.0027 (8)	0.0185 (7)	0.0018 (7)
C62	0.0402 (11)	0.0279 (10)	0.0419 (10)	0.0007 (8)	0.0180 (8)	0.0030 (7)
C63	0.0396 (11)	0.0515 (13)	0.0381 (10)	−0.0052 (9)	0.0149 (8)	−0.0002 (8)
C64	0.0459 (12)	0.0547 (14)	0.0379 (10)	0.0194 (10)	0.0158 (8)	0.0080 (9)
C65	0.0656 (14)	0.0322 (11)	0.0481 (11)	0.0169 (10)	0.0178 (10)	0.0040 (9)
C66	0.0484 (12)	0.0275 (10)	0.0421 (10)	−0.0001 (8)	0.0160 (8)	−0.0007 (7)

Geometric parameters (Å, º)

N1—C6	1.311 (2)	C42—C43	1.384 (2)
N1—C2	1.3577 (19)	C42—H42	0.9500
C2—N2	1.3280 (19)	C43—C44	1.372 (2)
C2—N3	1.3489 (19)	C43—H43	0.9500
N2—C27	1.4548 (19)	C44—C45	1.380 (3)
N2—H2	0.8800	C44—H44	0.9500
C27—C21	1.508 (2)	C45—C46	1.390 (2)
C27—H27A	0.9900	C45—H45	0.9500
C27—H27B	0.9900	C46—H46	0.9500
C21—C26	1.381 (2)	C5—N5	1.3667 (19)
C21—C22	1.386 (2)	C5—C6	1.425 (2)
C22—C23	1.380 (2)	N5—O5	1.2541 (17)
C22—H22	0.9500	C6—O6	1.3309 (18)
C23—C24	1.370 (2)	O6—C67	1.4560 (18)
C23—H23	0.9500	C67—C61	1.500 (2)
C24—C25	1.380 (2)	C67—H67A	0.9900
C24—H24	0.9500	C67—H67B	0.9900
C25—C26	1.382 (2)	C61—C66	1.385 (2)
C25—H25	0.9500	C61—C62	1.386 (2)
C26—H26	0.9500	C62—C63	1.378 (2)
N3—C4	1.3188 (19)	C62—H62	0.9500
C4—O4	1.3201 (18)	C63—C64	1.380 (3)
C4—C5	1.423 (2)	C63—H63	0.9500
O4—C47	1.4448 (17)	C64—C65	1.374 (3)
C47—C41	1.499 (2)	C64—H64	0.9500
C47—H47A	0.9900	C65—C66	1.381 (2)
C47—H47B	0.9900	C65—H65	0.9500
C41—C42	1.382 (2)	C66—H66	0.9500
C41—C46	1.384 (2)
C6—N1—C2	115.33 (13)	C41—C42—H42	119.7
N2—C2—N3	116.81 (14)	C43—C42—H42	119.7
N2—C2—N1	115.91 (13)	C44—C43—C42	120.62 (17)
N3—C2—N1	127.28 (14)	C44—C43—H43	119.7
C2—N2—C27	123.20 (13)	C42—C43—H43	119.7
C2—N2—H2	118.4	C43—C44—C45	119.51 (16)
C27—N2—H2	118.4	C43—C44—H44	120.2
N2—C27—C21	114.50 (12)	C45—C44—H44	120.2
N2—C27—H27A	108.6	C44—C45—C46	119.92 (17)
C21—C27—H27A	108.6	C44—C45—H45	120.0
N2—C27—H27B	108.6	C46—C45—H45	120.0
C21—C27—H27B	108.6	C41—C46—C45	120.77 (16)
H27A—C27—H27B	107.6	C41—C46—H46	119.6
C26—C21—C22	118.38 (15)	C45—C46—H46	119.6
C26—C21—C27	120.24 (13)	N5—C5—C4	129.88 (14)
C22—C21—C27	121.34 (14)	N5—C5—C6	116.04 (14)
C23—C22—C21	120.94 (15)	C4—C5—C6	114.06 (14)
C23—C22—H22	119.5	O5—N5—C5	118.59 (13)
C21—C22—H22	119.5	N1—C6—O6	119.84 (14)
C24—C23—C22	120.42 (15)	N1—C6—C5	123.95 (14)
C24—C23—H23	119.8	O6—C6—C5	116.21 (14)
C22—C23—H23	119.8	C6—O6—C67	117.63 (12)
C23—C24—C25	119.12 (16)	O6—C67—C61	113.13 (13)
C23—C24—H24	120.4	O6—C67—H67A	109.0
C25—C24—H24	120.4	C61—C67—H67A	109.0
C24—C25—C26	120.68 (16)	O6—C67—H67B	109.0
C24—C25—H25	119.7	C61—C67—H67B	109.0
C26—C25—H25	119.7	H67A—C67—H67B	107.8
C21—C26—C25	120.46 (15)	C66—C61—C62	119.01 (16)
C21—C26—H26	119.8	C66—C61—C67	120.32 (15)
C25—C26—H26	119.8	C62—C61—C67	120.57 (15)
C4—N3—C2	115.71 (13)	C63—C62—C61	120.77 (17)
N3—C4—O4	119.10 (13)	C63—C62—H62	119.6
N3—C4—C5	123.40 (13)	C61—C62—H62	119.6
O4—C4—C5	117.51 (14)	C62—C63—C64	119.86 (18)
C4—O4—C47	118.00 (12)	C62—C63—H63	120.1
O4—C47—C41	107.35 (13)	C64—C63—H63	120.1
O4—C47—H47A	110.2	C65—C64—C63	119.69 (17)
C41—C47—H47A	110.2	C65—C64—H64	120.2
O4—C47—H47B	110.2	C63—C64—H64	120.2
C41—C47—H47B	110.2	C64—C65—C66	120.68 (18)
H47A—C47—H47B	108.5	C64—C65—H65	119.7
C42—C41—C46	118.60 (15)	C66—C65—H65	119.7
C42—C41—C47	122.48 (14)	C65—C66—C61	119.97 (17)
C46—C41—C47	118.91 (15)	C65—C66—H66	120.0
C41—C42—C43	120.56 (16)	C61—C66—H66	120.0
C6—N1—C2—N2	−174.59 (13)	C42—C41—C46—C45	−1.4 (2)
C6—N1—C2—N3	4.8 (2)	C47—C41—C46—C45	177.33 (15)
N3—C2—N2—C27	−1.1 (2)	C44—C45—C46—C41	0.5 (3)
N1—C2—N2—C27	178.38 (13)	N3—C4—C5—N5	−177.06 (14)
C2—N2—C27—C21	75.42 (18)	O4—C4—C5—N5	2.5 (2)
N2—C27—C21—C26	−147.96 (15)	N3—C4—C5—C6	5.0 (2)
N2—C27—C21—C22	34.5 (2)	O4—C4—C5—C6	−175.50 (13)
C26—C21—C22—C23	0.0 (2)	C4—C5—N5—O5	1.7 (2)
C27—C21—C22—C23	177.56 (14)	C6—C5—N5—O5	179.60 (13)
C21—C22—C23—C24	−0.2 (3)	C2—N1—C6—O6	179.01 (13)
C22—C23—C24—C25	0.1 (3)	C2—N1—C6—C5	−1.0 (2)
C23—C24—C25—C26	0.2 (3)	N5—C5—C6—N1	178.37 (14)
C22—C21—C26—C25	0.3 (2)	C4—C5—C6—N1	−3.4 (2)
C27—C21—C26—C25	−177.26 (15)	N5—C5—C6—O6	−1.7 (2)
C24—C25—C26—C21	−0.4 (3)	C4—C5—C6—O6	176.58 (13)
N2—C2—N3—C4	176.05 (13)	N1—C6—O6—C67	1.7 (2)
N1—C2—N3—C4	−3.4 (2)	C5—C6—O6—C67	−178.23 (13)
C2—N3—C4—O4	178.55 (13)	C6—O6—C67—C61	−81.55 (18)
C2—N3—C4—C5	−1.9 (2)	O6—C67—C61—C66	121.65 (16)
N3—C4—O4—C47	−1.9 (2)	O6—C67—C61—C62	−62.1 (2)
C5—C4—O4—C47	178.60 (13)	C66—C61—C62—C63	0.1 (2)
C4—O4—C47—C41	−179.63 (12)	C67—C61—C62—C63	−176.22 (15)
O4—C47—C41—C42	−11.8 (2)	C61—C62—C63—C64	1.2 (2)
O4—C47—C41—C46	169.48 (13)	C62—C63—C64—C65	−1.1 (3)
C46—C41—C42—C43	1.3 (2)	C63—C64—C65—C66	−0.3 (3)
C47—C41—C42—C43	−177.44 (15)	C64—C65—C66—C61	1.7 (3)
C41—C42—C43—C44	−0.2 (3)	C62—C61—C66—C65	−1.5 (2)
C42—C43—C44—C45	−0.8 (3)	C67—C61—C66—C65	174.79 (16)
C43—C44—C45—C46	0.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O5^i	0.88	2.22	3.099 (2)	173
N2—H2···N5^i	0.88	2.28	3.023 (2)	143

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

(10) 2-Amino-4,6-bis(benzyloxy)pyrimidine

Crystal data

C18H17N3O2	F(000) = 1296
Mr = 307.35	Dx = 1.326 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 32.4902 (9) Å	Cell parameters from 3482 reflections
b = 7.5034 (2) Å	θ = 2.5–27.5°
c = 12.7804 (4) Å	µ = 0.09 mm^−1
β = 98.8790 (16)°	T = 150 K
V = 3078.36 (15) Å^3	Block, colourless
Z = 8	0.40 × 0.40 × 0.26 mm

Data collection

Kappa-CCD diffractometer	3482 independent reflections
Radiation source: fine-focus sealed X-ray tube	2677 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
φ scans, and ω scans with κ offsets	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −40→42
Tmin = 0.965, Tmax = 0.977	k = −8→9
13174 measured reflections	l = −16→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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.115	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0613P)^2 + 0.8375P] where P = (Fo^2 + 2Fc^2)/3
3482 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

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

	x	y	z	Uiso*/Ueq
N1	0.51399 (3)	0.30144 (14)	−0.10795 (7)	0.0216 (2)
C2	0.55011 (4)	0.37611 (16)	−0.12195 (9)	0.0211 (3)
N2	0.55466 (3)	0.42003 (16)	−0.22163 (8)	0.0272 (3)
N3	0.58237 (3)	0.41632 (14)	−0.04514 (8)	0.0220 (2)
C4	0.57639 (4)	0.37325 (17)	0.05097 (9)	0.0212 (3)
O4	0.60729 (3)	0.40530 (13)	0.13291 (6)	0.0263 (2)
C47	0.64548 (4)	0.47886 (18)	0.10783 (10)	0.0261 (3)
C41	0.67596 (4)	0.49060 (17)	0.20885 (10)	0.0243 (3)
C42	0.67281 (4)	0.38366 (19)	0.29557 (10)	0.0299 (3)
C43	0.70229 (4)	0.3945 (2)	0.38634 (11)	0.0366 (4)
C44	0.73511 (4)	0.5120 (2)	0.39122 (12)	0.0403 (4)
C45	0.73852 (4)	0.6191 (2)	0.30552 (13)	0.0421 (4)
C46	0.70906 (4)	0.6093 (2)	0.21481 (12)	0.0336 (3)
C5	0.54043 (4)	0.29522 (17)	0.07708 (9)	0.0216 (3)
C6	0.50982 (4)	0.26317 (16)	−0.00809 (9)	0.0200 (3)
O6	0.47240 (2)	0.18894 (12)	−0.00159 (6)	0.0242 (2)
C67	0.46354 (4)	0.14564 (17)	0.10187 (9)	0.0227 (3)
C61	0.42053 (4)	0.06749 (17)	0.09185 (9)	0.0219 (3)
C62	0.39349 (4)	0.06184 (18)	−0.00354 (10)	0.0272 (3)
C63	0.35409 (4)	−0.0129 (2)	−0.00843 (11)	0.0336 (3)
C64	0.34146 (4)	−0.08177 (19)	0.08176 (12)	0.0335 (3)
C66	0.40735 (4)	−0.00204 (18)	0.18197 (10)	0.0279 (3)
C65	0.36809 (4)	−0.07632 (19)	0.17698 (11)	0.0320 (3)
H2A	0.5343	0.3993	−0.2742	0.033*
H2B	0.5780	0.4695	−0.2343	0.033*
H47A	0.6404	0.5988	0.0762	0.031*
H47B	0.6568	0.4015	0.0562	0.031*
H42	0.6503	0.3022	0.2929	0.036*
H43	0.6998	0.3204	0.4454	0.044*
H44	0.7553	0.5191	0.4534	0.048*
H45	0.7611	0.7001	0.3085	0.051*
H46	0.7115	0.6843	0.1562	0.040*
H5	0.5373	0.2665	0.1478	0.026*
H67A	0.4653	0.2543	0.1462	0.027*
H67B	0.4842	0.0587	0.1363	0.027*
H62	0.4020	0.1093	−0.0658	0.033*
H63	0.3358	−0.0167	−0.0740	0.040*
H64	0.3145	−0.1327	0.0782	0.040*
H66	0.4255	0.0015	0.2478	0.033*
H65	0.3595	−0.1236	0.2391	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0217 (5)	0.0231 (6)	0.0198 (5)	0.0003 (4)	0.0025 (4)	0.0004 (4)
C2	0.0228 (6)	0.0189 (6)	0.0219 (6)	0.0029 (5)	0.0040 (5)	0.0012 (5)
N2	0.0243 (6)	0.0363 (7)	0.0208 (5)	−0.0046 (5)	0.0029 (4)	0.0052 (5)
N3	0.0224 (5)	0.0223 (6)	0.0213 (5)	−0.0002 (4)	0.0032 (4)	−0.0010 (4)
C4	0.0210 (6)	0.0203 (6)	0.0218 (6)	0.0020 (5)	0.0016 (5)	−0.0034 (5)
O4	0.0194 (4)	0.0382 (6)	0.0210 (4)	−0.0063 (4)	0.0025 (3)	−0.0035 (4)
C47	0.0220 (6)	0.0288 (7)	0.0283 (6)	−0.0043 (5)	0.0063 (5)	−0.0009 (6)
C41	0.0201 (6)	0.0246 (7)	0.0285 (6)	0.0007 (5)	0.0049 (5)	−0.0050 (5)
C42	0.0241 (7)	0.0336 (8)	0.0316 (7)	−0.0037 (6)	0.0031 (6)	0.0006 (6)
C43	0.0293 (7)	0.0489 (10)	0.0306 (7)	0.0030 (7)	0.0016 (6)	0.0036 (6)
C44	0.0246 (7)	0.0571 (11)	0.0363 (8)	0.0010 (7)	−0.0045 (6)	−0.0096 (7)
C45	0.0267 (7)	0.0488 (10)	0.0489 (9)	−0.0125 (7)	−0.0001 (7)	−0.0065 (8)
C46	0.0276 (7)	0.0347 (8)	0.0383 (8)	−0.0079 (6)	0.0042 (6)	0.0004 (6)
C5	0.0230 (6)	0.0242 (7)	0.0179 (5)	−0.0002 (5)	0.0043 (5)	−0.0009 (5)
C6	0.0207 (6)	0.0170 (6)	0.0228 (6)	0.0022 (5)	0.0047 (5)	−0.0004 (5)
O6	0.0211 (4)	0.0319 (5)	0.0199 (4)	−0.0049 (4)	0.0038 (3)	0.0003 (4)
C67	0.0254 (6)	0.0233 (7)	0.0196 (6)	−0.0010 (5)	0.0041 (5)	−0.0008 (5)
C61	0.0224 (6)	0.0177 (6)	0.0264 (6)	0.0017 (5)	0.0066 (5)	−0.0022 (5)
C62	0.0255 (7)	0.0277 (7)	0.0285 (6)	0.0008 (5)	0.0042 (5)	0.0032 (6)
C63	0.0239 (7)	0.0382 (9)	0.0366 (7)	0.0006 (6)	−0.0023 (6)	0.0018 (6)
C64	0.0222 (7)	0.0323 (8)	0.0466 (8)	−0.0022 (6)	0.0077 (6)	0.0009 (6)
C66	0.0309 (7)	0.0268 (7)	0.0264 (6)	−0.0031 (6)	0.0061 (5)	−0.0017 (5)
C65	0.0329 (7)	0.0299 (8)	0.0356 (7)	−0.0036 (6)	0.0136 (6)	0.0023 (6)

Geometric parameters (Å, º)

N1—C6	1.3353 (15)	C45—C46	1.387 (2)
N1—C2	1.3372 (16)	C45—H45	0.9500
C2—N2	1.3459 (15)	C46—H46	0.9500
C2—N3	1.3550 (15)	C5—C6	1.3776 (16)
N2—H2A	0.8800	C5—H5	0.9500
N2—H2B	0.8800	C6—O6	1.3516 (14)
N3—C4	1.3132 (16)	O6—C67	1.4332 (14)
C4—O4	1.3556 (14)	C67—C61	1.5026 (17)
C4—C5	1.3927 (18)	C67—H67A	0.9900
O4—C47	1.4388 (15)	C67—H67B	0.9900
C47—C41	1.5034 (17)	C61—C62	1.3890 (17)
C47—H47A	0.9900	C61—C66	1.3909 (18)
C47—H47B	0.9900	C62—C63	1.3904 (19)
C41—C42	1.3848 (19)	C62—H62	0.9500
C41—C46	1.3892 (18)	C63—C64	1.382 (2)
C42—C43	1.3881 (18)	C63—H63	0.9500
C42—H42	0.9500	C64—C65	1.381 (2)
C43—C44	1.378 (2)	C64—H64	0.9500
C43—H43	0.9500	C66—C65	1.3843 (19)
C44—C45	1.377 (2)	C66—H66	0.9500
C44—H44	0.9500	C65—H65	0.9500
C6—N1—C2	116.01 (10)	C45—C46—H46	119.7
N1—C2—N2	117.13 (10)	C41—C46—H46	119.7
N1—C2—N3	126.39 (11)	C6—C5—C4	114.46 (11)
N2—C2—N3	116.46 (11)	C6—C5—H5	122.8
C2—N2—H2A	120.0	C4—C5—H5	122.8
C2—N2—H2B	120.0	N1—C6—O6	111.85 (10)
H2A—N2—H2B	120.0	N1—C6—C5	123.40 (11)
C4—N3—C2	114.41 (10)	O6—C6—C5	124.75 (10)
N3—C4—O4	118.69 (11)	C6—O6—C67	117.43 (9)
N3—C4—C5	125.33 (11)	O6—C67—C61	109.05 (9)
O4—C4—C5	115.98 (10)	O6—C67—H67A	109.9
C4—O4—C47	117.21 (9)	C61—C67—H67A	109.9
O4—C47—C41	107.91 (10)	O6—C67—H67B	109.9
O4—C47—H47A	110.1	C61—C67—H67B	109.9
C41—C47—H47A	110.1	H67A—C67—H67B	108.3
O4—C47—H47B	110.1	C62—C61—C66	118.78 (11)
C41—C47—H47B	110.1	C62—C61—C67	122.72 (11)
H47A—C47—H47B	108.4	C66—C61—C67	118.50 (11)
C42—C41—C46	118.66 (12)	C61—C62—C63	120.33 (12)
C42—C41—C47	122.22 (11)	C61—C62—H62	119.8
C46—C41—C47	119.10 (12)	C63—C62—H62	119.8
C41—C42—C43	120.56 (13)	C64—C63—C62	120.21 (12)
C41—C42—H42	119.7	C64—C63—H63	119.9
C43—C42—H42	119.7	C62—C63—H63	119.9
C44—C43—C42	120.30 (14)	C65—C64—C63	119.85 (12)
C44—C43—H43	119.8	C65—C64—H64	120.1
C42—C43—H43	119.8	C63—C64—H64	120.1
C45—C44—C43	119.64 (13)	C65—C66—C61	120.81 (12)
C45—C44—H44	120.2	C65—C66—H66	119.6
C43—C44—H44	120.2	C61—C66—H66	119.6
C44—C45—C46	120.27 (14)	C64—C65—C66	120.01 (13)
C44—C45—H45	119.9	C64—C65—H65	120.0
C46—C45—H45	119.9	C66—C65—H65	120.0
C45—C46—C41	120.57 (14)
C6—N1—C2—N2	−178.39 (11)	N3—C4—C5—C6	0.26 (19)
C6—N1—C2—N3	−0.17 (19)	O4—C4—C5—C6	−179.49 (10)
N1—C2—N3—C4	0.95 (18)	C2—N1—C6—O6	179.78 (10)
N2—C2—N3—C4	179.17 (11)	C2—N1—C6—C5	−0.65 (18)
C2—N3—C4—O4	178.78 (11)	C4—C5—C6—N1	0.62 (18)
C2—N3—C4—C5	−0.97 (18)	C4—C5—C6—O6	−179.87 (11)
N3—C4—O4—C47	−2.34 (16)	N1—C6—O6—C67	−178.43 (10)
C5—C4—O4—C47	177.43 (11)	C5—C6—O6—C67	2.01 (17)
C4—O4—C47—C41	−175.99 (10)	C6—O6—C67—C61	179.24 (10)
O4—C47—C41—C42	23.68 (17)	O6—C67—C61—C62	−6.91 (17)
O4—C47—C41—C46	−158.05 (12)	O6—C67—C61—C66	173.05 (11)
C46—C41—C42—C43	−0.3 (2)	C66—C61—C62—C63	−0.3 (2)
C47—C41—C42—C43	177.98 (13)	C67—C61—C62—C63	179.66 (12)
C41—C42—C43—C44	0.0 (2)	C61—C62—C63—C64	0.2 (2)
C42—C43—C44—C45	0.1 (2)	C62—C63—C64—C65	0.0 (2)
C43—C44—C45—C46	0.2 (2)	C62—C61—C66—C65	0.3 (2)
C44—C45—C46—C41	−0.5 (2)	C67—C61—C66—C65	−179.70 (12)
C42—C41—C46—C45	0.5 (2)	C63—C64—C65—C66	0.0 (2)
C47—C41—C46—C45	−177.80 (13)	C61—C66—C65—C64	−0.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1^i	0.88	2.13	3.002 (2)	170
N2—H2B···O4^ii	0.88	2.27	3.013 (2)	142

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

(11) 2-Amino-4,6-bis(pyrrolidino)-5-nitrosopyrimidine hydrate

Crystal data

C24H38.20N12O3.10	F(000) = 1164
Mr = 544.47	Dx = 1.345 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 18.4687 (8) Å	Cell parameters from 4758 reflections
b = 8.1067 (3) Å	θ = 1.3–25.0°
c = 19.1880 (6) Å	µ = 0.10 mm^−1
β = 110.580 (2)°	T = 150 K
V = 2689.50 (17) Å^3	Plate, colourless
Z = 4	0.20 × 0.20 × 0.07 mm

Data collection

Kappa-CCD diffractometer	4758 independent reflections
Radiation source: fine-focus sealed X-ray tube	3200 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.060
φ scans and ω scans with κ offsets	θmax = 25.0°, θmin = 1.3°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −21→21
Tmin = 0.981, Tmax = 0.993	k = −8→9
50212 measured reflections	l = −22→22

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)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.236	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.1429P)^2 + 1.8403P] where P = (Fo^2 + 2Fc^2)/3
4758 reflections	(Δ/σ)max < 0.001
391 parameters	Δρmax = 0.52 e Å^−3
13 restraints	Δρmin = −0.35 e Å^−3

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
N11	0.19035 (14)	0.8837 (3)	0.07345 (12)	0.0298 (6)
C12	0.12823 (18)	0.8534 (4)	0.01186 (16)	0.0386 (8)
N12	0.13982 (17)	0.8564 (5)	−0.05275 (14)	0.0583 (10)
N13	0.05638 (16)	0.8135 (4)	0.00832 (14)	0.0475 (8)
C14	0.04130 (17)	0.8310 (4)	0.07010 (16)	0.0348 (7)
N14	−0.02471 (15)	0.7687 (4)	0.07128 (15)	0.0413 (7)
C141	−0.0795 (2)	0.6865 (5)	0.0052 (2)	0.0519 (10)
C142	−0.1421 (2)	0.6266 (8)	0.0317 (3)	0.0938 (19)
C14B	−0.0883 (12)	0.5790 (13)	0.1085 (7)	0.046*	0.20
C143	−0.1020 (4)	0.5981 (10)	0.1135 (3)	0.147 (6)	0.80
C144	−0.0439 (2)	0.7350 (5)	0.1381 (2)	0.0641 (12)
C15	0.09546 (18)	0.9172 (4)	0.13320 (17)	0.0357 (7)
N15A	0.0817 (2)	1.0183 (5)	0.1835 (2)	0.0406 (11)	0.792 (7)
O15A	0.01189 (15)	1.0505 (4)	0.17611 (16)	0.0486 (10)	0.792 (7)
N15B	0.0543 (9)	1.0309 (18)	0.1523 (8)	0.0406 (11)	0.21
O15B	0.0896 (6)	1.1434 (19)	0.1925 (6)	0.0486 (10)	0.21
C16	0.17468 (17)	0.9140 (4)	0.13551 (16)	0.0324 (7)
N16	0.23457 (15)	0.9401 (4)	0.19765 (14)	0.0409 (7)
C161	0.31478 (19)	0.9370 (5)	0.19899 (18)	0.0470 (9)
C163	0.3151 (2)	0.9155 (7)	0.3228 (2)	0.0724 (14)
C162	0.3621 (2)	0.9811 (7)	0.2789 (2)	0.0732 (14)
C164	0.2324 (2)	0.9560 (5)	0.27375 (17)	0.0524 (10)
N21	0.30211 (14)	0.8908 (3)	−0.07253 (13)	0.0289 (6)
C22	0.35854 (18)	0.8190 (4)	−0.01434 (16)	0.0336 (7)
N22	0.34027 (16)	0.7839 (4)	0.04550 (14)	0.0473 (8)
N23	0.42884 (15)	0.7696 (3)	−0.01199 (14)	0.0377 (7)
C24	0.45242 (17)	0.8242 (4)	−0.06643 (16)	0.0304 (7)
N24	0.52247 (14)	0.7748 (3)	−0.06330 (14)	0.0337 (6)
C241	0.57193 (18)	0.6725 (5)	−0.00080 (18)	0.0411 (8)
C242	0.6496 (2)	0.6778 (5)	−0.0101 (2)	0.0506 (9)
C243	0.6288 (2)	0.6893 (5)	−0.0928 (2)	0.0571 (11)
C244	0.5594 (2)	0.8051 (5)	−0.1178 (2)	0.0494 (9)
C25	0.40426 (17)	0.9355 (4)	−0.12318 (16)	0.0315 (7)
N25A	0.4435 (2)	1.0449 (4)	−0.14877 (17)	0.0387 (10)	0.887 (7)
O25A	0.40845 (14)	1.1702 (3)	−0.18357 (14)	0.0434 (9)	0.887 (7)
N25B	0.426 (2)	1.011 (4)	−0.1744 (13)	0.0387 (10)	0.11
O25B	0.4883 (12)	1.056 (3)	−0.1715 (12)	0.0434 (9)	0.11
C26	0.32333 (17)	0.9402 (3)	−0.12923 (15)	0.0289 (7)
N26	0.26710 (15)	0.9911 (3)	−0.19068 (13)	0.0347 (6)
C261	0.18556 (18)	0.9925 (4)	−0.19584 (17)	0.0378 (8)
C262	0.1419 (2)	1.0545 (5)	−0.27375 (18)	0.0480 (9)
C263	0.1902 (2)	0.9920 (5)	−0.31777 (18)	0.0505 (10)
C264	0.2731 (2)	1.0189 (5)	−0.26436 (17)	0.0438 (9)
O1	0.45652 (16)	0.6786 (5)	0.18190 (16)	0.0644 (13)	0.902 (8)
O2	−0.0446 (8)	0.310 (2)	0.1852 (8)	0.078 (5)	0.20
H12A	0.1016	0.8331	−0.0943	0.070*
H12B	0.1857	0.8817	−0.0539	0.070*
H14A	−0.0545	0.5934	−0.0109	0.062*
H14B	−0.1001	0.7651	−0.0366	0.062*
H14C	−0.1706	0.5311	0.0027	0.113*
H14D	−0.1787	0.7150	0.0326	0.113*
H14F	−0.1178	0.5433	0.1401	0.055*	0.20
H14E	−0.0532	0.4889	0.1059	0.055*	0.20
H14I	−0.0761	0.4892	0.1228	0.176*	0.80
H14J	−0.1392	0.6033	0.1400	0.176*	0.80
H14H	−0.0765	0.8222	0.1481	0.077*
H14G	0.0025	0.7156	0.1829	0.077*
H16A	0.3224	1.0189	0.1639	0.056*
H16B	0.3287	0.8262	0.1860	0.056*
H16E	0.3291	0.9710	0.3717	0.087*
H16F	0.3223	0.7950	0.3307	0.087*
H16D	0.4136	0.9282	0.2947	0.088*
H16C	0.3688	1.1021	0.2850	0.088*
H16H	0.1953	0.8771	0.2820	0.063*
H16G	0.2182	1.0694	0.2831	0.063*
H22A	0.3735	0.7313	0.0834	0.057*
H22B	0.2950	0.8133	0.0470	0.057*
H24A	0.5522	0.5581	−0.0045	0.049*
H24B	0.5749	0.7198	0.0477	0.049*
H24D	0.6799	0.7751	0.0152	0.061*
H24C	0.6798	0.5765	0.0098	0.061*
H24E	0.6150	0.5796	−0.1164	0.068*
H24F	0.6723	0.7350	−0.1056	0.068*
H24H	0.5760	0.9216	−0.1164	0.059*
H24G	0.5243	0.7780	−0.1687	0.059*
H26A	0.1781	1.0672	−0.1581	0.045*
H26B	0.1682	0.8803	−0.1886	0.045*
H26D	0.1388	1.1764	−0.2750	0.058*
H26C	0.0889	1.0084	−0.2933	0.058*
H26E	0.1798	1.0560	−0.3642	0.061*
H26F	0.1800	0.8738	−0.3304	0.061*
H26H	0.3090	0.9392	−0.2740	0.053*
H26G	0.2909	1.1324	−0.2686	0.053*
H11	0.465 (3)	0.643 (7)	0.2340 (11)	0.097*	0.902 (8)
H12	0.5056 (17)	0.735 (6)	0.185 (3)	0.097*	0.902 (8)
H21	−0.011 (9)	0.214 (16)	0.186 (10)	0.094*	0.20
H22	−0.048 (13)	0.33 (3)	0.236 (5)	0.094*	0.20

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0288 (13)	0.0387 (14)	0.0229 (12)	0.0035 (11)	0.0103 (10)	0.0018 (10)
C12	0.0362 (18)	0.054 (2)	0.0277 (16)	−0.0090 (15)	0.0135 (13)	0.0004 (14)
N12	0.0438 (18)	0.108 (3)	0.0256 (14)	−0.0287 (18)	0.0157 (13)	−0.0085 (15)
N13	0.0399 (16)	0.077 (2)	0.0277 (14)	−0.0175 (15)	0.0140 (12)	−0.0066 (13)
C14	0.0276 (17)	0.0473 (19)	0.0296 (16)	0.0029 (14)	0.0104 (13)	0.0021 (13)
N14	0.0288 (14)	0.0591 (18)	0.0386 (15)	−0.0024 (13)	0.0150 (12)	−0.0028 (13)
C141	0.0327 (19)	0.071 (3)	0.048 (2)	−0.0123 (17)	0.0096 (15)	−0.0060 (18)
C142	0.046 (3)	0.145 (5)	0.100 (4)	−0.043 (3)	0.039 (3)	−0.054 (4)
C143	0.148 (8)	0.235 (12)	0.107 (6)	−0.138 (9)	0.108 (6)	−0.087 (6)
C144	0.047 (2)	0.100 (3)	0.061 (2)	−0.016 (2)	0.038 (2)	−0.023 (2)
C15	0.0333 (17)	0.0429 (19)	0.0334 (16)	0.0047 (14)	0.0149 (13)	−0.0036 (13)
N15A	0.039 (3)	0.051 (2)	0.034 (2)	0.0127 (19)	0.0157 (18)	0.000 (2)
O15A	0.0289 (16)	0.077 (2)	0.0404 (17)	0.0121 (14)	0.0124 (12)	−0.0140 (14)
N15B	0.039 (3)	0.051 (2)	0.034 (2)	0.0127 (19)	0.0157 (18)	0.000 (2)
O15B	0.0289 (16)	0.077 (2)	0.0404 (17)	0.0121 (14)	0.0124 (12)	−0.0140 (14)
C16	0.0305 (17)	0.0385 (17)	0.0296 (16)	0.0025 (13)	0.0124 (13)	−0.0025 (13)
N16	0.0318 (15)	0.0644 (19)	0.0268 (14)	−0.0025 (13)	0.0109 (11)	−0.0078 (12)
C161	0.0308 (18)	0.070 (3)	0.0378 (18)	−0.0045 (17)	0.0095 (14)	−0.0053 (17)
C163	0.065 (3)	0.113 (4)	0.0281 (19)	0.018 (3)	0.0027 (18)	−0.012 (2)
C162	0.038 (2)	0.117 (4)	0.051 (2)	−0.001 (2)	−0.0014 (18)	−0.026 (2)
C164	0.050 (2)	0.079 (3)	0.0283 (17)	−0.0028 (19)	0.0134 (15)	−0.0105 (17)
N21	0.0308 (13)	0.0320 (13)	0.0259 (12)	0.0006 (11)	0.0124 (10)	0.0006 (10)
C22	0.0366 (17)	0.0381 (17)	0.0279 (15)	0.0067 (14)	0.0134 (13)	0.0016 (13)
N22	0.0384 (16)	0.075 (2)	0.0331 (15)	0.0246 (15)	0.0190 (12)	0.0182 (14)
N23	0.0378 (15)	0.0497 (17)	0.0313 (13)	0.0141 (13)	0.0192 (12)	0.0082 (12)
C24	0.0304 (17)	0.0310 (16)	0.0315 (16)	−0.0019 (12)	0.0130 (13)	−0.0038 (12)
N24	0.0297 (14)	0.0390 (15)	0.0367 (14)	0.0019 (11)	0.0169 (11)	0.0036 (11)
C241	0.0301 (17)	0.054 (2)	0.0410 (18)	0.0079 (15)	0.0150 (14)	0.0043 (15)
C242	0.0366 (19)	0.056 (2)	0.065 (2)	0.0061 (17)	0.0264 (17)	0.0050 (18)
C243	0.060 (2)	0.059 (2)	0.072 (3)	0.0125 (19)	0.047 (2)	0.008 (2)
C244	0.050 (2)	0.058 (2)	0.056 (2)	0.0078 (18)	0.0371 (18)	0.0099 (18)
C25	0.0343 (17)	0.0311 (16)	0.0335 (16)	−0.0004 (13)	0.0176 (13)	0.0015 (12)
N25A	0.048 (2)	0.035 (2)	0.041 (2)	−0.0024 (14)	0.0255 (19)	0.0000 (15)
O25A	0.0395 (16)	0.0413 (16)	0.0514 (16)	0.0032 (12)	0.0186 (12)	0.0148 (12)
N25B	0.048 (2)	0.035 (2)	0.041 (2)	−0.0024 (14)	0.0255 (19)	0.0000 (15)
O25B	0.0395 (16)	0.0413 (16)	0.0514 (16)	0.0032 (12)	0.0186 (12)	0.0148 (12)
C26	0.0322 (16)	0.0263 (15)	0.0302 (15)	0.0006 (12)	0.0134 (13)	0.0020 (12)
N26	0.0318 (15)	0.0453 (16)	0.0282 (13)	0.0016 (12)	0.0122 (11)	0.0089 (11)
C261	0.0340 (18)	0.0475 (19)	0.0325 (16)	0.0018 (15)	0.0123 (13)	0.0057 (14)
C262	0.0361 (19)	0.059 (2)	0.0427 (19)	−0.0014 (17)	0.0065 (15)	0.0124 (16)
C263	0.060 (2)	0.059 (2)	0.0296 (17)	−0.0038 (19)	0.0125 (16)	0.0082 (16)
C264	0.048 (2)	0.055 (2)	0.0319 (17)	0.0040 (17)	0.0184 (15)	0.0112 (15)
O1	0.0348 (17)	0.105 (3)	0.0509 (19)	−0.0032 (16)	0.0124 (13)	0.0390 (17)
O2	0.040 (8)	0.137 (15)	0.056 (8)	−0.005 (8)	0.015 (6)	−0.058 (9)

Geometric parameters (Å, º)

N11—C16	1.343 (4)	N21—C26	1.341 (4)
N11—C12	1.349 (4)	N21—C22	1.362 (4)
C12—N12	1.330 (4)	C22—N22	1.336 (4)
C12—N13	1.344 (4)	C22—N23	1.344 (4)
N12—H12A	0.8800	N22—H22A	0.8800
N12—H12B	0.8800	N22—H22B	0.8800
N13—C14	1.317 (4)	N23—C24	1.340 (4)
C14—N14	1.327 (4)	C24—N24	1.335 (4)
C14—C15	1.450 (4)	C24—C25	1.453 (4)
N14—C144	1.471 (4)	N24—C244	1.456 (4)
N14—C141	1.473 (4)	N24—C241	1.480 (4)
C141—C142	1.498 (6)	C241—C242	1.507 (5)
C141—H14A	0.9900	C241—H24A	0.9900
C141—H14B	0.9900	C241—H24B	0.9900
C142—C143	1.499 (5)	C242—C243	1.498 (5)
C142—C14B	1.510 (5)	C242—H24D	0.9900
C142—H14C	0.9900	C242—H24C	0.9900
C142—H14D	0.9900	C243—C244	1.524 (5)
C14B—C144	1.505 (5)	C243—H24E	0.9900
C14B—H14F	0.9900	C243—H24F	0.9900
C14B—H14E	0.9900	C244—H24H	0.9900
C143—C144	1.500 (4)	C244—H24G	0.9900
C143—H14I	0.9900	C25—N25B	1.334 (5)
C143—H14J	0.9900	C25—N25A	1.342 (4)
C144—H14H	0.9900	C25—C26	1.458 (4)
C144—H14G	0.9900	N25A—O25A	1.262 (3)
C15—N15B	1.326 (5)	N25B—O25B	1.19 (4)
C15—N15A	1.357 (5)	C26—N26	1.333 (4)
C15—C16	1.448 (4)	N26—C264	1.474 (4)
N15A—O15A	1.273 (4)	N26—C261	1.474 (4)
N15B—O15B	1.22 (2)	C261—C262	1.513 (4)
C16—N16	1.328 (4)	C261—H26A	0.9900
N16—C161	1.473 (4)	C261—H26B	0.9900
N16—C164	1.480 (4)	C262—C263	1.515 (5)
C161—C162	1.516 (5)	C262—H26D	0.9900
C161—H16A	0.9900	C262—H26C	0.9900
C161—H16B	0.9900	C263—C264	1.529 (5)
C163—C162	1.504 (6)	C263—H26E	0.9900
C163—C164	1.521 (5)	C263—H26F	0.9900
C163—H16E	0.9900	C264—H26H	0.9900
C163—H16F	0.9900	C264—H26G	0.9900
C162—H16D	0.9900	O1—H11	1.000 (2)
C162—H16C	0.9900	O1—H12	1.000 (2)
C164—H16H	0.9900	O2—H21	1.000 (5)
C164—H16G	0.9900	O2—H22	1.000 (5)
C16—N11—C12	115.3 (3)	N16—C164—C163	102.9 (3)
N12—C12—N13	115.9 (3)	N16—C164—H16H	111.2
N12—C12—N11	116.6 (3)	C163—C164—H16H	111.2
N13—C12—N11	127.5 (3)	N16—C164—H16G	111.2
C12—N12—H12A	120.0	C163—C164—H16G	111.2
C12—N12—H12B	120.0	H16H—C164—H16G	109.1
H12A—N12—H12B	120.0	C26—N21—C22	115.8 (2)
C14—N13—C12	116.5 (3)	N22—C22—N23	116.1 (3)
N13—C14—N14	117.4 (3)	N22—C22—N21	116.4 (3)
N13—C14—C15	120.1 (3)	N23—C22—N21	127.4 (3)
N14—C14—C15	122.5 (3)	C22—N22—H22A	120.0
C14—N14—C144	126.2 (3)	C22—N22—H22B	120.0
C14—N14—C141	120.9 (3)	H22A—N22—H22B	120.0
C144—N14—C141	111.3 (3)	C24—N23—C22	116.7 (3)
N14—C141—C142	103.5 (3)	N24—C24—N23	116.2 (3)
N14—C141—H14A	111.1	N24—C24—C25	123.2 (3)
C142—C141—H14A	111.1	N23—C24—C25	120.6 (3)
N14—C141—H14B	111.1	C24—N24—C244	127.5 (3)
C142—C141—H14B	111.1	C24—N24—C241	121.1 (2)
H14A—C141—H14B	109.0	C244—N24—C241	111.4 (3)
C141—C142—C143	104.4 (4)	N24—C241—C242	103.3 (3)
C141—C142—C14B	95.3 (10)	N24—C241—H24A	111.1
C143—C142—C14B	12.9 (13)	C242—C241—H24A	111.1
C141—C142—H14C	112.7	N24—C241—H24B	111.1
C143—C142—H14C	115.9	C242—C241—H24B	111.1
C14B—C142—H14C	112.7	H24A—C241—H24B	109.1
C141—C142—H14D	112.7	C243—C242—C241	103.1 (3)
C143—C142—H14D	100.4	C243—C242—H24D	111.1
C14B—C142—H14D	112.7	C241—C242—H24D	111.1
H14C—C142—H14D	110.2	C243—C242—H24C	111.1
C144—C14B—C142	103.8 (5)	C241—C242—H24C	111.1
C144—C14B—H14F	111.0	H24D—C242—H24C	109.1
C142—C14B—H14F	111.0	C242—C243—C244	104.2 (3)
C144—C14B—H14E	111.0	C242—C243—H24E	110.9
C142—C14B—H14E	111.0	C244—C243—H24E	110.9
H14F—C14B—H14E	109.0	C242—C243—H24F	110.9
C142—C143—C144	104.6 (4)	C244—C243—H24F	110.9
C142—C143—H14I	110.8	H24E—C243—H24F	108.9
C144—C143—H14I	110.8	N24—C244—C243	103.0 (3)
C142—C143—H14J	110.8	N24—C244—H24H	111.2
C144—C143—H14J	110.8	C243—C244—H24H	111.2
H14I—C143—H14J	108.9	N24—C244—H24G	111.2
N14—C144—C143	103.2 (3)	C243—C244—H24G	111.2
N14—C144—C14B	95.4 (9)	H24H—C244—H24G	109.1
C143—C144—C14B	12.9 (13)	N25B—C25—N25A	24.1 (13)
N14—C144—H14H	112.7	N25B—C25—C24	124.9 (16)
C143—C144—H14H	100.0	N25A—C25—C24	114.7 (3)
C14B—C144—H14H	112.7	N25B—C25—C26	119.8 (16)
N14—C144—H14G	112.7	N25A—C25—C26	128.6 (3)
C143—C144—H14G	117.5	C24—C25—C26	114.6 (2)
C14B—C144—H14G	112.7	O25A—N25A—C25	118.9 (3)
H14H—C144—H14G	110.2	O25B—N25B—C25	130 (3)
N15B—C15—N15A	27.6 (6)	N26—C26—N21	116.8 (3)
N15B—C15—C16	132.5 (9)	N26—C26—C25	122.4 (3)
N15A—C15—C16	115.4 (3)	N21—C26—C25	120.8 (3)
N15B—C15—C14	105.8 (8)	C26—N26—C264	126.7 (3)
N15A—C15—C14	129.6 (3)	C26—N26—C261	121.4 (2)
C16—C15—C14	114.2 (3)	C264—N26—C261	110.7 (2)
O15A—N15A—C15	118.7 (3)	N26—C261—C262	104.2 (3)
O15B—N15B—C15	117.5 (13)	N26—C261—H26A	110.9
N16—C16—N11	117.0 (3)	C262—C261—H26A	110.9
N16—C16—C15	122.6 (3)	N26—C261—H26B	110.9
N11—C16—C15	120.4 (3)	C262—C261—H26B	110.9
C16—N16—C161	121.9 (3)	H26A—C261—H26B	108.9
C16—N16—C164	126.7 (3)	C261—C262—C263	103.1 (3)
C161—N16—C164	111.1 (3)	C261—C262—H26D	111.1
N16—C161—C162	103.4 (3)	C263—C262—H26D	111.1
N16—C161—H16A	111.1	C261—C262—H26C	111.1
C162—C161—H16A	111.1	C263—C262—H26C	111.1
N16—C161—H16B	111.1	H26D—C262—H26C	109.1
C162—C161—H16B	111.1	C262—C263—C264	103.0 (3)
H16A—C161—H16B	109.0	C262—C263—H26E	111.2
C162—C163—C164	103.2 (3)	C264—C263—H26E	111.2
C162—C163—H16E	111.1	C262—C263—H26F	111.2
C164—C163—H16E	111.1	C264—C263—H26F	111.2
C162—C163—H16F	111.1	H26E—C263—H26F	109.1
C164—C163—H16F	111.1	N26—C264—C263	103.1 (3)
H16E—C163—H16F	109.1	N26—C264—H26H	111.1
C163—C162—C161	104.0 (3)	C263—C264—H26H	111.1
C163—C162—H16D	111.0	N26—C264—H26G	111.1
C161—C162—H16D	111.0	C263—C264—H26G	111.1
C163—C162—H16C	111.0	H26H—C264—H26G	109.1
C161—C162—H16C	111.0	H11—O1—H12	105 (4)
H16D—C162—H16C	109.0	H21—O2—H22	111.1 (8)
C16—N11—C12—N12	166.7 (3)	N16—C161—C162—C163	30.2 (4)
C16—N11—C12—N13	−16.3 (5)	C16—N16—C164—C163	158.3 (4)
N12—C12—N13—C14	−171.4 (3)	C161—N16—C164—C163	−14.9 (4)
N11—C12—N13—C14	11.7 (6)	C162—C163—C164—N16	33.3 (4)
C12—N13—C14—N14	−169.8 (3)	C26—N21—C22—N22	173.7 (3)
C12—N13—C14—C15	10.9 (5)	C26—N21—C22—N23	−11.0 (5)
N13—C14—N14—C144	162.8 (3)	N22—C22—N23—C24	−170.7 (3)
C15—C14—N14—C144	−17.9 (5)	N21—C22—N23—C24	14.0 (5)
N13—C14—N14—C141	−1.3 (5)	C22—N23—C24—N24	179.7 (3)
C15—C14—N14—C141	178.0 (3)	C22—N23—C24—C25	1.9 (4)
C14—N14—C141—C142	176.6 (4)	N23—C24—N24—C244	174.9 (3)
C144—N14—C141—C142	10.3 (5)	C25—C24—N24—C244	−7.3 (5)
N14—C141—C142—C143	−28.8 (6)	N23—C24—N24—C241	−3.0 (4)
N14—C141—C142—C14B	−38.0 (8)	C25—C24—N24—C241	174.8 (3)
C141—C142—C14B—C144	55.4 (16)	C24—N24—C241—C242	−167.9 (3)
C143—C142—C14B—C144	−80.3 (14)	C244—N24—C241—C242	13.9 (4)
C141—C142—C143—C144	37.1 (7)	N24—C241—C242—C243	−32.3 (4)
C14B—C142—C143—C144	83.1 (16)	C241—C242—C243—C244	39.2 (4)
C14—N14—C144—C143	−153.2 (5)	C24—N24—C244—C243	−168.1 (3)
C141—N14—C144—C143	12.2 (6)	C241—N24—C244—C243	10.0 (4)
C14—N14—C144—C14B	−142.7 (8)	C242—C243—C244—N24	−30.3 (4)
C141—N14—C144—C14B	22.6 (9)	N24—C24—C25—N25B	−5.5 (17)
C142—C143—C144—N14	−30.0 (7)	N23—C24—C25—N25B	172.2 (17)
C142—C143—C144—C14B	−83.7 (16)	N24—C24—C25—N25A	−30.7 (4)
C142—C14B—C144—N14	−48.3 (15)	N23—C24—C25—N25A	147.0 (3)
C142—C14B—C144—C143	79.6 (14)	N24—C24—C25—C26	164.5 (3)
N13—C14—C15—N15B	127.8 (9)	N23—C24—C25—C26	−17.8 (4)
N14—C14—C15—N15B	−51.5 (9)	N25B—C25—N25A—O25A	76 (4)
N13—C14—C15—N15A	143.7 (4)	C24—C25—N25A—O25A	−162.8 (3)
N14—C14—C15—N15A	−35.5 (6)	C26—C25—N25A—O25A	−0.6 (5)
N13—C14—C15—C16	−25.8 (4)	N25A—C25—N25B—O25B	41 (3)
N14—C14—C15—C16	154.9 (3)	C24—C25—N25B—O25B	−31 (4)
N15B—C15—N15A—O15A	32.7 (19)	C26—C25—N25B—O25B	160 (3)
C16—C15—N15A—O15A	167.4 (3)	C22—N21—C26—N26	171.6 (3)
C14—C15—N15A—O15A	−2.0 (6)	C22—N21—C26—C25	−7.7 (4)
N15A—C15—N15B—O15B	43.7 (14)	N25B—C25—C26—N26	12.2 (17)
C16—C15—N15B—O15B	−17 (2)	N25A—C25—C26—N26	39.5 (5)
C14—C15—N15B—O15B	−163.4 (13)	C24—C25—C26—N26	−158.3 (3)
C12—N11—C16—N16	178.3 (3)	N25B—C25—C26—N21	−168.6 (16)
C12—N11—C16—C15	−1.7 (4)	N25A—C25—C26—N21	−141.3 (3)
N15B—C15—C16—N16	56.3 (11)	C24—C25—C26—N21	20.9 (4)
N15A—C15—C16—N16	29.8 (5)	N21—C26—N26—C264	−166.8 (3)
C14—C15—C16—N16	−159.1 (3)	C25—C26—N26—C264	12.4 (5)
N15B—C15—C16—N11	−123.7 (10)	N21—C26—N26—C261	−0.1 (4)
N15A—C15—C16—N11	−150.3 (3)	C25—C26—N26—C261	179.1 (3)
C14—C15—C16—N11	20.8 (4)	C26—N26—C261—C262	−178.9 (3)
N11—C16—N16—C161	0.3 (5)	C264—N26—C261—C262	−10.3 (4)
C15—C16—N16—C161	−179.8 (3)	N26—C261—C262—C263	31.1 (4)
N11—C16—N16—C164	−172.2 (3)	C261—C262—C263—C264	−40.1 (4)
C15—C16—N16—C164	7.7 (5)	C26—N26—C264—C263	153.4 (3)
C16—N16—C161—C162	177.1 (4)	C261—N26—C264—C263	−14.5 (4)
C164—N16—C161—C162	−9.3 (4)	C262—C263—C264—N26	33.4 (4)
C164—C163—C162—C161	−39.8 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N12—H12B···N21	0.88	2.30	3.163 (4)	166
N22—H22B···N11	0.88	2.24	3.107 (4)	169
N12—H12A···O15A^i	0.88	2.33	3.059 (4)	140
N22—H22A···O1	0.88	2.02	2.870 (4)	163
O1—H11···O15A^ii	1.00	1.79	2.779 (4)	171
O1—H11···N15A^ii	1.00	2.29	3.184 (5)	149
O1—H12···O25A^iii	1.00	1.77	2.769 (4)	176
O1—H12···N25A^iii	1.00	2.24	3.109 (5)	145

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