Ethyl N-(2-benzyl­amino-6-benzyl­oxy-5-nitro­sopyrimidin-4-yl)­glycinate: sheets built from a three-centre N—H...(N,O), and two-centre C—H...O and C—H...π(arene) hydrogen bonds

In the title compound, C₂₂H₂₃N₅O₄, the mol­ecules are linked into chains by a three-centre N—H...(N,O) hydrogen bond, reinforced by a two-centre C—H...O hydrogen bond, and the chains are further linked into sheets by a combination of C—H...O and C—H...π(arene) hydrogen bonds.

S1. Comment

We report here the molecular and supramolecular structure of the title compound, ethyl N-(2-benzylamino-6-benzyloxy-5-nitrosopyrimidin-4-yl)glycinate, (I) (Fig. 1), which we have studied in order to compare the interplay of the molecular and supramolecular structure in (I) with that in the analogue (II) (Quesada, Marchal et al., 2002; Quesada, Low et al., 2002), which differs from (I) in having an unsubstituted amino N2 atom, with no N²-benzyl group, as is present in (I). In (II), the molecules are linked into chains by a combination of a three-centred N—H···(N,O) hydrogen bond and an N—H···π(arene) interaction, involving different N—H bonds of the 2-amino group in the two types of interaction. In (I), with no NH₂ group, a different pattern of supramolecular aggregation must occur.

In (I), the amino N4 forms the intramolecular N—H···O hydrogen bond typical of 4-amino-5-nitrosopyrimidines (Quesada, Marchal et al., 2002; Quesada, Low et al., 2002) and the amino N2 atom acts as hydrogen-bond donor to the nitroso atoms N5ⁱ and O5ⁱ in an almost planar three-centre interaction (see Table 2 for symmetry code), propagation of this interaction produces a chain running parallel to the [010] direction and generated by the 2₁-screw axis along (0, y, 1/4) (Fig. 2). This [010] chain is further reinforced by a C—H···O hydrogen bond, with the nitroso O5 atom again acting as the acceptor (Table 2 and Fig. 2), and the chain thus contains three different ring motifs of S(6), R²₁(3) and R¹₂(11) types (Bernstein et al., 1995).

Two chains of this type, related to one another by centres of inversion and thus antiparallel, run through each unit cell, generated by the screw axes along (0, y, 1/4) and (0, -y, 3/4), and these chains are linked into (100) sheets by a combination of C—H···O and C—H···π(arene) hydrogen bonds (Table 2 and Fig. 3). Atoms C7 (via H7B) and C22, which are part of the chain along (0, y, 1/4), both act as hydrogen-bond donors to carbonyl O81ⁱⁱ which lies in the chain along (0, -y, 3/4) [symmetry code: (ii) x, -y + 1/2, z + 1/2]. Similarly, atoms C7 and C22 in the molecule at (-x, 0.5 + y, 0.5 - z), which also lies in the (0, y, 1/4) chain, act as donors to O81 in the molecule at (-x, 1 - y, -z), which itself lies in the chain along (0, -y, -0.25). In this manner, each [010] chain is linked by C—H···O hydrogen bonds to the two neighbouring chains in the [001] direction, so generating a (100) sheet.

The linking of the [010] chains is further reinforced by two distinct C—H···π(arene) interactions. Atoms C7 (via H7A) and C67 (via H67A) act as hydrogen-bond donors, respectively, to the centroid Cg2ⁱⁱ of the ring (C21–C26)ⁱⁱ and to the centroid Cg3ⁱⁱⁱ of the ring (C61–C66)ⁱⁱⁱ. These two molecules lie in the chains along (0, -y, 3/4) and (0, -y, -0.25), respectively, and hence these interactions (Fig. 3) reinforce the (100) sheet.

All of the C—H···O and C—H···π(arene) interactions have H···A and D···A distances which are reasonably short for their types and all except one have D—H···A angles above 150° (Table 2). However, the co-operative action of the many hydrogen bonds may be more significant than the properties of the individual interactions. It is striking that, in the enforced absence of an N—H···π(arene) hydrogen bond of the type found in (II), the structure of (I) nonetheless has adjusted to maximize the effects of the weaker hydrogen bonds, in particular, by engaging both of the aryl rings in the molecule.

Within the molecule of (I), the C—C, C—N and N—O distances (Table 1) exhibit the usual pattern found (Quesada, Marchal et al., 2002; Quesada, Low et al., 2002) in 2,4-diamino-5-nitrosopyrimidines, consistent with extensive charge delocalization, as in (Ia) (see Scheme). The conformation, as defined by the key torsion angles (Table 1), has atoms C27 and C67 effectively coplanar with the pyrimidine ring, but the phenyl rings are rotated out of this plane. The ester group has an unusual conformation (Fig. 1), as demonstrated by the (-)synclinal torsion angle C8—O82—C9—C10 (Table 1).

S2. Experimental

A solution of ethyl glycinate hydrochloride (0.51 mmol) in ethanol (5 ml) was neutralized by KOH (0.51 mmol). 2-Benzylamino-4,6-bisbenzyloxy-5-nitosopyrimidine (0.47 mmol) were then added and the mixture was kept at 333 K for 6 h. When the mixture had cooled to room temperature, distilled water (50 ml) was added and ethanol was eliminated by reduced pressure until a solid precipitate appeared. The solid was then filtered off and washed with distilled water (yield 86%, m.p. 396 K). Analysis found: C 62.70, H 5.50, N 16.62%; C₂₂H₂₃N₅O₄ requires C 62.40, H 5.62, N 16.07%. Crystals suitable for single-crystal X-ray diffraction analysis were grown from a solution in ethanol–water (1:1, v/v).

S3. Refinement

Compound (I) crystallized in the monoclinic system; the space group P2₁/c was uniquely assigned from the systematic absences. H atoms were treated as riding, with C—H distances in the range 0.95–0.99 Å and N—H distances of 0.88 Å.

Computing details

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

Figures

	Fig. 1. A view of the molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Part of the crystal structure of (I), showing the formation of a chain along [010]. Atoms marked with an asterisk (*) or hash (#) are at the symmetry positions (-x, 0.5 + y, 0.5 - z) and (-x, -0.5 + y, 0.5 - z), respectively.
	Fig. 3. Stereoview of part of the structure of (I), showing the C—H···O and C—H···π(arene) hydrogen bonds which link the [010] chains into a (100) sheet. For the sake of clarity, the unit-cell box has been omitted and only H atoms involved in the motifs shown are included.

Ethyl N-[2-benzylamino-6-benzyloxy-5-nitrosopyrimidin-4-yl]glycinate

Crystal data

C22H23N5O4	F(000) = 888
Mr = 421.45	Dx = 1.363 Mg m^−3
Monoclinic, P21/c	Melting point: 396 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 15.2278 (8) Å	Cell parameters from 4644 reflections
b = 15.8992 (5) Å	θ = 3.0–25.0°
c = 8.5558 (3) Å	µ = 0.10 mm^−1
β = 97.5860 (11)°	T = 120 K
V = 2053.31 (14) Å^3	Needle, purple
Z = 4	0.40 × 0.05 × 0.02 mm

Data collection

Nonius KappaCCD diffractometer	1861 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tube	Rint = 0.200
Graphite monochromator	θmax = 25.0°, θmin = 3.0°
ϕ scans, and ω scans with κ offsets	h = −18→18
24714 measured reflections	k = −18→18
3619 independent reflections	l = −10→9

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.176	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0658P)^2 + 1.1859P] where P = (Fo^2 + 2Fc^2)/3
3619 reflections	(Δ/σ)max < 0.001
281 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

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
N1	−0.0187 (2)	0.3075 (2)	0.2239 (4)	0.0245 (8)
C2	0.0506 (3)	0.3350 (3)	0.3311 (4)	0.0239 (10)
N2	0.0590 (2)	0.4176 (2)	0.3421 (4)	0.0253 (8)
C27	0.1239 (3)	0.4596 (3)	0.4548 (5)	0.0263 (10)
C21	0.2143 (3)	0.4660 (2)	0.4009 (5)	0.0248 (10)
C22	0.2867 (3)	0.4234 (3)	0.4784 (5)	0.0269 (10)
C23	0.3690 (3)	0.4312 (3)	0.4307 (5)	0.0330 (11)
C24	0.3813 (3)	0.4810 (3)	0.3038 (5)	0.0325 (11)
C25	0.3102 (3)	0.5240 (3)	0.2236 (5)	0.0324 (11)
C26	0.2276 (3)	0.5166 (3)	0.2734 (5)	0.0309 (11)
N3	0.1087 (2)	0.2870 (2)	0.4246 (4)	0.0239 (8)
C4	0.0945 (2)	0.2044 (3)	0.4154 (4)	0.0214 (9)
N4	0.1494 (2)	0.1539 (2)	0.5065 (4)	0.0254 (8)
C7	0.2333 (2)	0.1838 (3)	0.5859 (4)	0.0263 (10)
C8	0.3013 (3)	0.1837 (2)	0.4729 (5)	0.0251 (10)
O81	0.28688 (18)	0.16395 (18)	0.3365 (3)	0.0336 (8)
O82	0.38064 (17)	0.20902 (18)	0.5446 (3)	0.0307 (7)
C9	0.4508 (3)	0.2097 (3)	0.4442 (5)	0.0356 (12)
C10	0.4846 (3)	0.1237 (3)	0.4187 (6)	0.0457 (13)
C5	0.0225 (2)	0.1675 (3)	0.3114 (4)	0.0223 (10)
N5	0.0049 (2)	0.0859 (2)	0.2857 (4)	0.0284 (9)
O5	0.05466 (19)	0.03165 (18)	0.3646 (3)	0.0345 (8)
C6	−0.0312 (2)	0.2273 (3)	0.2183 (4)	0.0225 (10)
O6	−0.09866 (17)	0.19484 (17)	0.1202 (3)	0.0285 (7)
C67	−0.1553 (3)	0.2533 (3)	0.0206 (5)	0.0295 (10)
C61	−0.2196 (2)	0.2975 (3)	0.1104 (4)	0.0248 (10)
C62	−0.2114 (3)	0.3827 (3)	0.1432 (5)	0.0298 (11)
C63	−0.2713 (3)	0.4233 (3)	0.2247 (5)	0.0369 (12)
C64	−0.3403 (3)	0.3792 (3)	0.2756 (5)	0.0411 (13)
C65	−0.3501 (3)	0.2950 (3)	0.2425 (5)	0.0387 (12)
C66	−0.2908 (3)	0.2541 (3)	0.1583 (5)	0.0310 (11)
H2	0.0231	0.4489	0.2772	0.030*
H27A	0.1295	0.4285	0.5559	0.032*
H27B	0.1024	0.5169	0.4743	0.032*
H22	0.2793	0.3883	0.5656	0.032*
H23	0.4180	0.4020	0.4859	0.040*
H24	0.4384	0.4858	0.2714	0.039*
H25	0.3180	0.5582	0.1354	0.039*
H26	0.1789	0.5468	0.2193	0.037*
H4	0.1342	0.1011	0.5186	0.030*
H7A	0.2535	0.1471	0.6770	0.032*
H7B	0.2263	0.2416	0.6258	0.032*
H9A	0.5002	0.2453	0.4933	0.043*
H9B	0.4278	0.2348	0.3410	0.043*
H10A	0.5338	0.1271	0.3559	0.055*
H10B	0.4369	0.0895	0.3627	0.055*
H10C	0.5053	0.0977	0.5209	0.055*
H67A	−0.1885	0.2219	−0.0682	0.035*
H67B	−0.1178	0.2955	−0.0240	0.035*
H62	−0.1639	0.4135	0.1092	0.036*
H63	−0.2651	0.4819	0.2458	0.044*
H64	−0.3809	0.4071	0.3334	0.049*
H65	−0.3976	0.2646	0.2774	0.046*
H66	−0.2990	0.1962	0.1332	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0219 (19)	0.029 (2)	0.0227 (19)	−0.0002 (17)	0.0032 (14)	−0.0018 (15)
C2	0.022 (2)	0.030 (3)	0.021 (2)	−0.001 (2)	0.0071 (18)	0.0003 (19)
N2	0.023 (2)	0.024 (2)	0.028 (2)	0.0002 (17)	0.0008 (15)	−0.0005 (15)
C27	0.028 (2)	0.027 (3)	0.025 (2)	−0.003 (2)	0.0075 (18)	−0.0038 (18)
C21	0.027 (2)	0.021 (3)	0.026 (2)	−0.0053 (19)	0.0028 (18)	−0.0035 (18)
C22	0.032 (3)	0.027 (3)	0.020 (2)	0.000 (2)	−0.0008 (18)	−0.0007 (18)
C23	0.023 (2)	0.041 (3)	0.034 (3)	0.002 (2)	−0.0030 (18)	−0.003 (2)
C24	0.026 (3)	0.037 (3)	0.036 (3)	−0.003 (2)	0.008 (2)	0.000 (2)
C25	0.031 (3)	0.032 (3)	0.035 (3)	−0.008 (2)	0.008 (2)	0.003 (2)
C26	0.027 (3)	0.036 (3)	0.029 (3)	0.003 (2)	−0.0022 (18)	0.001 (2)
N3	0.025 (2)	0.022 (2)	0.0243 (19)	0.0016 (16)	0.0035 (15)	0.0020 (15)
C4	0.023 (2)	0.022 (3)	0.019 (2)	0.000 (2)	0.0056 (17)	0.0010 (18)
N4	0.023 (2)	0.025 (2)	0.027 (2)	−0.0027 (16)	0.0017 (15)	0.0026 (16)
C7	0.025 (2)	0.034 (3)	0.020 (2)	0.000 (2)	0.0005 (17)	0.0049 (18)
C8	0.021 (2)	0.023 (3)	0.031 (3)	0.0004 (19)	0.0002 (18)	0.0069 (19)
O81	0.0330 (18)	0.044 (2)	0.0230 (18)	−0.0003 (15)	0.0016 (12)	−0.0038 (14)
O82	0.0253 (17)	0.0385 (19)	0.0286 (17)	0.0002 (14)	0.0050 (13)	−0.0020 (13)
C9	0.023 (2)	0.049 (3)	0.036 (3)	0.000 (2)	0.009 (2)	−0.002 (2)
C10	0.030 (3)	0.049 (3)	0.058 (3)	0.008 (2)	0.006 (2)	0.000 (3)
C5	0.024 (2)	0.024 (3)	0.019 (2)	0.0011 (19)	0.0044 (17)	−0.0007 (18)
N5	0.029 (2)	0.025 (2)	0.032 (2)	0.0043 (18)	0.0085 (16)	0.0009 (17)
O5	0.0328 (17)	0.0261 (19)	0.0438 (19)	−0.0006 (15)	0.0026 (14)	0.0008 (14)
C6	0.021 (2)	0.029 (3)	0.018 (2)	−0.006 (2)	0.0043 (17)	−0.0049 (18)
O6	0.0265 (16)	0.0294 (18)	0.0282 (17)	0.0015 (14)	−0.0016 (12)	−0.0027 (13)
C67	0.025 (2)	0.042 (3)	0.021 (2)	0.000 (2)	−0.0022 (17)	−0.001 (2)
C61	0.022 (2)	0.033 (3)	0.018 (2)	−0.004 (2)	−0.0008 (17)	0.0025 (19)
C62	0.030 (3)	0.037 (3)	0.022 (2)	0.003 (2)	−0.0016 (18)	0.003 (2)
C63	0.042 (3)	0.038 (3)	0.028 (3)	0.009 (2)	−0.006 (2)	−0.004 (2)
C64	0.038 (3)	0.059 (4)	0.026 (3)	0.021 (3)	0.002 (2)	−0.003 (2)
C65	0.031 (3)	0.061 (4)	0.024 (3)	0.000 (3)	0.002 (2)	0.002 (2)
C66	0.029 (3)	0.038 (3)	0.024 (2)	−0.003 (2)	−0.0022 (19)	0.001 (2)

Geometric parameters (Å, º)

N1—C2	1.376 (5)	N4—H4	0.8800
C2—N3	1.348 (5)	C7—C8	1.507 (6)
N3—C4	1.330 (5)	C7—H7A	0.9900
C4—C5	1.443 (5)	C7—H7B	0.9900
C5—C6	1.427 (6)	C8—O81	1.201 (5)
C6—N1	1.288 (5)	C8—O82	1.343 (5)
C2—N2	1.321 (5)	O82—C9	1.456 (5)
C4—N4	1.334 (5)	C9—C10	1.488 (6)
C5—N5	1.337 (5)	C9—H9A	0.9900
N5—O5	1.280 (4)	C9—H9B	0.9900
C6—O6	1.342 (5)	C10—H10A	0.9800
N2—C27	1.450 (5)	C10—H10B	0.9800
N2—H2	0.8800	C10—H10C	0.9800
C27—C21	1.512 (6)	O6—C67	1.462 (5)
C27—H27A	0.9900	C67—C61	1.497 (6)
C27—H27B	0.9900	C67—H67A	0.9900
C21—C22	1.386 (6)	C67—H67B	0.9900
C21—C26	1.392 (6)	C61—C62	1.386 (6)
C22—C23	1.375 (6)	C61—C66	1.392 (6)
C22—H22	0.9500	C62—C63	1.380 (6)
C23—C24	1.376 (6)	C62—H62	0.9500
C23—H23	0.9500	C63—C64	1.381 (6)
C24—C25	1.383 (6)	C63—H63	0.9500
C24—H24	0.9500	C64—C65	1.373 (6)
C25—C26	1.386 (6)	C64—H64	0.9500
C25—H25	0.9500	C65—C66	1.388 (6)
C26—H26	0.9500	C65—H65	0.9500
N4—C7	1.447 (5)	C66—H66	0.9500
C6—N1—C2	115.8 (3)	O82—C8—C7	111.1 (3)
N2—C2—N3	118.1 (4)	C8—O82—C9	114.8 (3)
N2—C2—N1	115.0 (4)	O82—C9—C10	112.0 (4)
N3—C2—N1	126.9 (4)	O82—C9—H9A	109.2
C2—N2—C27	123.8 (3)	C10—C9—H9A	109.2
C2—N2—H2	118.1	O82—C9—H9B	109.2
C27—N2—H2	118.1	C10—C9—H9B	109.2
N2—C27—C21	113.4 (3)	H9A—C9—H9B	107.9
N2—C27—H27A	108.9	C9—C10—H10A	109.5
C21—C27—H27A	108.9	C9—C10—H10B	109.5
N2—C27—H27B	108.9	H10A—C10—H10B	109.5
C21—C27—H27B	108.9	C9—C10—H10C	109.5
H27A—C27—H27B	107.7	H10A—C10—H10C	109.5
C22—C21—C26	118.0 (4)	H10B—C10—H10C	109.5
C22—C21—C27	121.3 (4)	N5—C5—C6	117.8 (4)
C26—C21—C27	120.7 (4)	N5—C5—C4	128.0 (4)
C23—C22—C21	120.8 (4)	C6—C5—C4	114.0 (4)
C23—C22—H22	119.6	O5—N5—C5	118.3 (3)
C21—C22—H22	119.6	N1—C6—O6	120.0 (4)
C22—C23—C24	120.7 (4)	N1—C6—C5	124.6 (4)
C22—C23—H23	119.7	O6—C6—C5	115.3 (4)
C24—C23—H23	119.7	C6—O6—C67	117.7 (3)
C23—C24—C25	119.8 (4)	O6—C67—C61	112.0 (3)
C23—C24—H24	120.1	O6—C67—H67A	109.2
C25—C24—H24	120.1	C61—C67—H67A	109.2
C24—C25—C26	119.2 (4)	O6—C67—H67B	109.2
C24—C25—H25	120.4	C61—C67—H67B	109.2
C26—C25—H25	120.4	H67A—C67—H67B	107.9
C25—C26—C21	121.4 (4)	C62—C61—C66	118.5 (4)
C25—C26—H26	119.3	C62—C61—C67	121.0 (4)
C21—C26—H26	119.3	C66—C61—C67	120.4 (4)
C4—N3—C2	115.8 (3)	C63—C62—C61	120.8 (4)
N3—C4—N4	118.4 (4)	C63—C62—H62	119.6
N3—C4—C5	122.8 (4)	C61—C62—H62	119.6
N4—C4—C5	118.8 (4)	C62—C63—C64	120.2 (5)
C4—N4—C7	121.5 (3)	C62—C63—H63	119.9
C4—N4—H4	119.3	C64—C63—H63	119.9
C7—N4—H4	119.3	C65—C64—C63	119.8 (4)
N4—C7—C8	109.7 (3)	C65—C64—H64	120.1
N4—C7—H7A	109.7	C63—C64—H64	120.1
C8—C7—H7A	109.7	C64—C65—C66	120.2 (4)
N4—C7—H7B	109.7	C64—C65—H65	119.9
C8—C7—H7B	109.7	C66—C65—H65	119.9
H7A—C7—H7B	108.2	C65—C66—C61	120.4 (4)
O81—C8—O82	124.1 (4)	C65—C66—H66	119.8
O81—C8—C7	124.9 (4)	C61—C66—H66	119.8
C6—N1—C2—N2	−176.0 (3)	N4—C7—C8—O82	−178.2 (3)
C6—N1—C2—N3	3.3 (6)	O81—C8—O82—C9	−1.0 (6)
N3—C2—N2—C27	−3.5 (6)	C7—C8—O82—C9	179.2 (3)
N1—C2—N2—C27	175.8 (3)	C8—O82—C9—C10	−76.9 (4)
C2—N2—C27—C21	83.1 (5)	N3—C4—C5—N5	175.8 (4)
N2—C27—C21—C22	−113.8 (4)	N4—C4—C5—N5	−4.2 (6)
N2—C27—C21—C26	67.6 (5)	N3—C4—C5—C6	0.7 (5)
C26—C21—C22—C23	0.2 (6)	N4—C4—C5—C6	−179.3 (3)
C27—C21—C22—C23	−178.5 (4)	C6—C5—N5—O5	177.5 (3)
C21—C22—C23—C24	−0.7 (6)	C4—C5—N5—O5	2.6 (6)
C22—C23—C24—C25	0.3 (7)	C2—N1—C6—O6	178.3 (3)
C23—C24—C25—C26	0.5 (6)	C2—N1—C6—C5	−1.5 (5)
C24—C25—C26—C21	−0.9 (6)	N5—C5—C6—N1	−175.9 (3)
C22—C21—C26—C25	0.5 (6)	C4—C5—C6—N1	−0.3 (6)
C27—C21—C26—C25	179.3 (4)	N5—C5—C6—O6	4.3 (5)
N2—C2—N3—C4	176.4 (3)	C4—C5—C6—O6	179.9 (3)
N1—C2—N3—C4	−2.8 (6)	N1—C6—O6—C67	0.9 (5)
C2—N3—C4—N4	−179.3 (3)	O6—C67—C61—C66	−71.6 (5)
C2—N3—C4—C5	0.7 (5)	C66—C61—C62—C63	1.5 (6)
N3—C4—N4—C7	−14.2 (5)	C67—C61—C62—C63	179.3 (4)
C5—C4—N4—C7	165.8 (3)	C61—C62—C63—C64	0.4 (6)
C4—N4—C7—C8	−81.4 (5)	C62—C63—C64—C65	−1.2 (6)
N4—C7—C8—O81	1.9 (6)	C63—C64—C65—C66	0.1 (6)
C5—C6—O6—C67	−179.3 (3)	C64—C65—C66—C61	1.8 (6)
C6—O6—C67—C61	−77.5 (4)	C62—C61—C66—C65	−2.5 (6)
O6—C67—C61—C62	110.6 (4)	C67—C61—C66—C65	179.6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O5	0.88	2.00	2.621 (4)	126
N2—H2···O5^i	0.88	2.06	2.933 (4)	175
N2—H2···N5^i	0.88	2.27	3.004 (5)	141
C62—H62···O5^i	0.95	2.50	3.369 (5)	152
C7—H7B···O81^ii	0.99	2.43	3.265 (5)	141
C22—H22···O81^ii	0.95	2.45	3.364 (4)	161
C7—H7A···Cg2^ii	0.99	2.47	3.439 (4)	165
C67—H67A···Cg3^iii	0.99	2.52	3.499 (4)	172

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