(E)-3-{2-Amino-4-eth­oxy-6-[N-(4-meth­oxy­phen­yl)-N-methyl­amino]pyrimidin-5-yl}-1-phenyl­prop-2-en-1-one: a boat-shaped pyrimidine ring and a chain of hydrogen-bonded R⁴₂(8) and R²₂(20) rings

In the title compound, C₂₃H₂₄N₄O₃, the pyrimidine ring adopts an almost perfect boat conformation, and the bond distances provide evidence for some polarization of the mol­ecular-electronic structure. Two independent N-H...O hydrogen bonds link the mol­ecules into chains of edge-fused R²₄(8) and R²₂(20) rings.

S1. Comment

As part of a programme aimed at the synthesis of new heterocyclic compounds with potential biological activity, we have attempted the functionalization of the pyrimidine ring at position 5 via the modification of 5-formylpyrimidines as a route to the preparation of intermediates for the synthesis of polycyclic heterocyclic compounds. We report here the molecular and supramolecular structures of one such intermediate, (E)-3-{2-amino-4-ethoxy-6-[N-(4-methoxyphenyl)-N– methylamino]pyrimidin-5-yl}1-phenylprop-2-en-1-one, (I) (Fig. 1), formed by a base-catalysed condensation between acetophenone and 2-amino-4-chloro-6-[N-(4-methoxyphenyl)-N– methylamino]pyrimidin3–5-carbaldehyde, where the condensation at the formyl group is accompanied by solvolysis at position 4 (see Scheme).

The pyrimidine ring in (I) adopts an almost perfect boat conformation; the ring-puckering parameters (Cremer & Pople, 1975) for the atom sequence N1, C2, N3, C4, C4, C6 are θ = 88 (2)° and ϕ = 241 (2)°, with a total puckering amplitude Q of 0.105 (2) Å. The ideal values of the puckering angles for a boat conformation are θ = 90° and ϕ = (60n)°, where n represents zero or an integer. Atoms C2 and C5, at the stem and stern of the boat, are displaced by 0.061 (2) and 0.060 (2) Å, respectively, on one side of the mean plane of the pyrimidine ring; the other four ring atoms all lie on the opposite side of the mean plane, displaced from it by distances ranging from 0.026 (2) Å for N1 to 0.034 (2) Å for C6. More striking are the displacements from this plane of the substituent atoms N2 and C51, bonded to C2 and C5, which are 0.209 (2) and 0.450 (2) Å, respectively; the substituent atoms O4 and N6, bonded to C4 and C6, are displaced from the opposite face of the mean plane by 0.071 (2) and 0.097 (2) Å, respectively, as indicated schematically at (A) (see Scheme). We have previously observed such nonplanarity in a number of extensively-substituted pyrimidine derivatives exhibiting boat (Quesada et al., 2004) or twist-boat (Melguizo et al., 2003; Quesada et al., 2002, 2003) conformations, and by comparison with less extensively-substituted analogues, the distortions from planarity were ascribed to steric factors (Melguizo et al., 2003). The occurrence here of a nonplanar pyrimidine ring in the presence of three adjacent substituents on the ring is certainly consistent with the earlier interpretation.

The propenone side chain is effectively planar as indicated by the relevant torsion angles (Table 2). Although the steric effects arising from the three adjacent substituents at atoms C4, C5 and C6 appear to be responsible for the puckering of the pyrimidine ring, the conformational arrangement of the methyl and aryl substituents at atom N6 is somewhat surprising, particularly as there appear to be no intramolecular C—H···π(arene) interactions that could lock the C61–C66 ring into position. The exocyclic angles at atoms C4 and C64 show the usual deviations from 120° observed for alkoxy groups, with the alkyl C atom effectively coplanar with the adjacent ring, but similar effects are found at none of the other substituent sites.

Despite the nonplanarity of the pyrimidine ring, the bond distances in (I) (Table 1) provide some evidence for polarization of the molecular–electronic structure. The C4—N3 bond is significantly shorter than any other C—N bond present; the N2—C2, C2—N1 and N1—C6 bonds are very similar in length; the C51—C52 and C53—O53 bonds are both long for their types (Allen et al., 1987); and the C6—N6, C5—C51 and C52—C53 bonds are somewhat short for their types. These observations taken together indicate a modest contribution from the polarized form (Ia).

The molecules of (I) are linked by two independent N—H···O hydrogen bonds (Table 2) into a chain of edge-fused rings along [100]. Amino atom N2 in the molecule at (x, y, z) acts as a hydrogen-bond donor to atoms O53 in the two molecules at (-1 + x, y, z) and (1 - x, 1 - y, 1 - z). Propagation of these two hydrogen bonds by translation and inversion forms a chain in which R²₄(8) (Bernstein et al., 1995) rings centred at (n, 1/2, 1/2), where n represents zero or an integer, alternate with R²₂(20) rings centred at (n + 1/2, 1/2, 1/2), where n represents zero or an integer (Fig. 2). In these two hydrogen bonds, both the donor atom N2 and the acceptor atom O53 carry partial charges arising from the polarization of the molecular–electronic structure [see (Ia) in the Scheme], and hence they can be regarded as charge-assisted or resonance-assisted hydrogen bonds (Gilli et al., 1994).

Related literature

For related literature, see: Allen et al. (1987); Bernstein et al. (1995); Gilli et al. (1994); Melguizo et al. (2003); Quesada et al. (2002, 2003, 2004).

S2. Experimental

Sodium hydroxide (two pellets) was added to a solution containing 1 mmol each of 2-amino-4-chloro-6-[N-(4-methoxyphenyl)-N-methylamino]- pyrimidine-5-carbaldehyde and acetophenone in ethanol (10 ml). The solution was stirred for 2 h at room temperature and then heated under reflux for 20 h. The resulting precipitate of sodium chloride was removed by filtration. The filtrate was diluted with water (2 ml), briefly heated and then allowed to cool to ambient temperature. The solid product (I) was collected by filtration, washed with ethanol and dried. Crystallization from ethanol gave yellow block crystals suitable for single-crystal X-ray diffraction (yield 20%, m.p. 427–428 K). HRMS: m/z found: 404.1848; C₂₃H₂₄N₄O₃ requires: 404.1832.

S3. Refinement

Crystals of compound (I) are triclinic; the space group P1 was selected and confirmed by the structure analysis. All H atoms were located in difference maps and then treated as riding atoms in geometrically idealized positions, with C—H distances of 0.95 Å (aromatic and alkene), 0.98 Å (CH₃) or 0.99 Å (CH₂), and N—H of 0.86 Å, and with U_iso(H) = kU_eq(carrier), where k = 1.5 for the methyl groups and k = 1.2 for all other H atoms.

Computing details

Data collection: COLLECT (Hooft, 1999); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: Sir2004 (Burla et al., 2005); program(s) used to refine structure: OSCAIL (McArdle, 2003) and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PRPKAPPA (Ferguson, 1999).

Figures

	Fig. 1. The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A stereoview of part of the crystal structure of (I), showing the formation of a hydrogen-bonded chain of edge-fused R^24(8) and R^22(20) rings along [100]. For the sake of clarity, H atoms bonded to C atoms have been omitted.

(E)-3-{2-Amino-4-ethoxy-6-[N-(4-methoxyphenyl)-N– methylamino]pyrimidin-5-yl}-1-phenylprop-2-en-1-one

Crystal data

C23H24N4O3	Z = 2
Mr = 404.46	F(000) = 428
Triclinic, P1	Dx = 1.297 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.1975 (14) Å	Cell parameters from 4750 reflections
b = 10.959 (2) Å	θ = 3.2–27.5°
c = 11.046 (2) Å	µ = 0.09 mm^−1
α = 94.079 (16)°	T = 120 K
β = 109.845 (11)°	Block, yellow
γ = 113.339 (10)°	0.49 × 0.29 × 0.24 mm
V = 1035.5 (3) Å^3

Data collection

Bruker–Nonius KappaCCD diffractometer	4750 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	3263 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.2°
ϕ & ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −14→14
Tmin = 0.963, Tmax = 0.979	l = −14→14
28433 measured reflections

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) = 0.113	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0427P)^2 + 0.5503P] where P = (Fo^2 + 2Fc^2)/3
4750 reflections	(Δ/σ)max < 0.001
274 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

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

	x	y	z	Uiso*/Ueq
O4	0.39883 (14)	0.61904 (12)	0.15800 (12)	0.0219 (3)
O53	0.92580 (13)	0.62061 (13)	0.36906 (12)	0.0222 (3)
O64	0.73235 (15)	0.06065 (14)	0.17267 (12)	0.0268 (3)
N1	0.25866 (15)	0.35949 (14)	0.38173 (13)	0.0180 (3)
N2	0.08042 (16)	0.43894 (16)	0.37328 (14)	0.0231 (3)
N3	0.22967 (16)	0.52434 (15)	0.25593 (14)	0.0190 (3)
N6	0.44717 (16)	0.28859 (14)	0.40677 (13)	0.0177 (3)
C2	0.19416 (18)	0.44197 (17)	0.33706 (16)	0.0174 (3)
C4	0.35242 (19)	0.53545 (17)	0.23372 (15)	0.0174 (3)
C5	0.44646 (18)	0.47014 (17)	0.28849 (15)	0.0162 (3)
C6	0.38285 (18)	0.37268 (17)	0.35725 (15)	0.0163 (3)
C41	0.3157 (2)	0.69814 (19)	0.10697 (17)	0.0236 (4)
C42	0.1966 (2)	0.6271 (2)	−0.03242 (19)	0.0302 (4)
C51	0.60208 (18)	0.51407 (16)	0.29572 (16)	0.0165 (3)
C52	0.67729 (19)	0.59807 (17)	0.23191 (16)	0.0188 (3)
C53	0.84342 (19)	0.64473 (17)	0.27128 (16)	0.0173 (3)
C531	0.92078 (19)	0.72991 (17)	0.19313 (16)	0.0166 (3)
C532	0.84398 (19)	0.71857 (17)	0.05883 (16)	0.0195 (4)
C533	0.9241 (2)	0.79514 (18)	−0.00961 (17)	0.0225 (4)
C534	1.0808 (2)	0.88642 (18)	0.05627 (18)	0.0229 (4)
C535	1.1576 (2)	0.90017 (18)	0.19058 (18)	0.0222 (4)
C536	1.07862 (19)	0.82127 (18)	0.25831 (17)	0.0199 (4)
C61	0.52692 (19)	0.23891 (16)	0.34633 (16)	0.0172 (3)
C62	0.46871 (19)	0.19130 (17)	0.20922 (16)	0.0182 (3)
C63	0.5409 (2)	0.13391 (17)	0.15439 (16)	0.0198 (4)
C64	0.6712 (2)	0.12235 (17)	0.23539 (17)	0.0197 (4)
C65	0.7315 (2)	0.17189 (18)	0.37160 (17)	0.0219 (4)
C66	0.6590 (2)	0.22980 (18)	0.42594 (17)	0.0206 (4)
C67	0.8618 (2)	0.0416 (2)	0.25462 (19)	0.0317 (5)
C68	0.3825 (2)	0.20324 (18)	0.48873 (17)	0.0225 (4)
H2A	0.0452	0.4977	0.3540	0.028*
H2B	0.0708	0.4014	0.4375	0.028*
H41A	0.3907	0.7901	0.1083	0.028*
H41B	0.2630	0.7098	0.1644	0.028*
H42A	0.2476	0.6086	−0.0874	0.045*
H42B	0.1491	0.6859	−0.0684	0.045*
H42C	0.1157	0.5407	−0.0322	0.045*
H51	0.6619	0.4785	0.3547	0.020*
H52	0.6213	0.6264	0.1614	0.023*
H532	0.7360	0.6579	0.0140	0.023*
H533	0.8718	0.7853	−0.1018	0.027*
H534	1.1357	0.9395	0.0093	0.027*
H535	1.2644	0.9639	0.2360	0.027*
H536	1.1321	0.8292	0.3498	0.024*
H62	0.3791	0.1983	0.1532	0.022*
H63	0.5010	0.1023	0.0610	0.024*
H65	0.8221	0.1662	0.4275	0.026*
H66	0.7007	0.2637	0.5192	0.025*
H67A	0.9502	0.1309	0.3042	0.048*
H67B	0.8912	−0.0074	0.1991	0.048*
H67C	0.8327	−0.0119	0.3168	0.048*
H68A	0.3681	0.2584	0.5523	0.034*
H68B	0.4547	0.1680	0.5368	0.034*
H68C	0.2818	0.1264	0.4317	0.034*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O4	0.0234 (6)	0.0268 (7)	0.0251 (7)	0.0157 (5)	0.0135 (5)	0.0146 (5)
O53	0.0206 (6)	0.0282 (7)	0.0211 (6)	0.0123 (5)	0.0095 (5)	0.0115 (5)
O64	0.0326 (7)	0.0356 (8)	0.0222 (7)	0.0237 (6)	0.0124 (6)	0.0062 (6)
N1	0.0158 (7)	0.0200 (7)	0.0170 (7)	0.0072 (6)	0.0062 (6)	0.0040 (6)
N2	0.0226 (8)	0.0312 (9)	0.0249 (8)	0.0166 (7)	0.0136 (6)	0.0133 (7)
N3	0.0177 (7)	0.0236 (8)	0.0176 (7)	0.0107 (6)	0.0073 (6)	0.0058 (6)
N6	0.0203 (7)	0.0197 (7)	0.0185 (7)	0.0107 (6)	0.0112 (6)	0.0072 (6)
C2	0.0144 (8)	0.0193 (8)	0.0152 (8)	0.0065 (7)	0.0040 (6)	0.0016 (7)
C4	0.0188 (8)	0.0181 (8)	0.0133 (8)	0.0069 (7)	0.0059 (7)	0.0029 (6)
C5	0.0156 (8)	0.0182 (8)	0.0143 (8)	0.0079 (7)	0.0052 (6)	0.0025 (6)
C6	0.0152 (8)	0.0171 (8)	0.0134 (8)	0.0064 (7)	0.0037 (6)	0.0009 (6)
C41	0.0282 (9)	0.0249 (9)	0.0264 (10)	0.0172 (8)	0.0135 (8)	0.0116 (8)
C42	0.0315 (10)	0.0313 (11)	0.0308 (11)	0.0190 (9)	0.0094 (8)	0.0110 (8)
C51	0.0159 (8)	0.0168 (8)	0.0162 (8)	0.0079 (7)	0.0056 (7)	0.0016 (6)
C52	0.0177 (8)	0.0212 (9)	0.0186 (8)	0.0088 (7)	0.0083 (7)	0.0067 (7)
C53	0.0196 (8)	0.0170 (8)	0.0173 (8)	0.0095 (7)	0.0081 (7)	0.0037 (7)
C531	0.0190 (8)	0.0165 (8)	0.0191 (8)	0.0106 (7)	0.0098 (7)	0.0055 (6)
C532	0.0181 (8)	0.0196 (9)	0.0195 (9)	0.0079 (7)	0.0070 (7)	0.0030 (7)
C533	0.0264 (9)	0.0243 (9)	0.0183 (9)	0.0124 (8)	0.0092 (7)	0.0068 (7)
C534	0.0276 (9)	0.0208 (9)	0.0257 (9)	0.0112 (8)	0.0154 (8)	0.0101 (7)
C535	0.0178 (8)	0.0189 (9)	0.0267 (9)	0.0055 (7)	0.0087 (7)	0.0045 (7)
C536	0.0191 (8)	0.0236 (9)	0.0177 (8)	0.0103 (7)	0.0073 (7)	0.0059 (7)
C61	0.0184 (8)	0.0146 (8)	0.0197 (8)	0.0068 (7)	0.0094 (7)	0.0055 (7)
C62	0.0157 (8)	0.0171 (8)	0.0183 (8)	0.0059 (7)	0.0045 (7)	0.0046 (7)
C63	0.0227 (9)	0.0191 (9)	0.0160 (8)	0.0082 (7)	0.0074 (7)	0.0029 (7)
C64	0.0227 (9)	0.0186 (9)	0.0217 (9)	0.0103 (7)	0.0120 (7)	0.0050 (7)
C65	0.0210 (9)	0.0264 (9)	0.0199 (9)	0.0140 (8)	0.0059 (7)	0.0066 (7)
C66	0.0235 (9)	0.0227 (9)	0.0149 (8)	0.0113 (7)	0.0060 (7)	0.0028 (7)
C67	0.0375 (11)	0.0420 (12)	0.0306 (10)	0.0297 (10)	0.0161 (9)	0.0109 (9)
C68	0.0279 (9)	0.0240 (9)	0.0224 (9)	0.0140 (8)	0.0141 (8)	0.0101 (7)

Geometric parameters (Å, º)

O4—C4	1.341 (2)	C53—C531	1.494 (2)
O4—C41	1.4545 (19)	C531—C532	1.392 (2)
O64—C64	1.373 (2)	C531—C536	1.395 (2)
O64—C67	1.428 (2)	C532—C533	1.382 (2)
N1—C2	1.344 (2)	C532—H532	0.95
C2—N3	1.351 (2)	C533—C534	1.388 (3)
N3—C4	1.317 (2)	C533—H533	0.95
C4—C5	1.418 (2)	C534—C535	1.387 (2)
C5—C6	1.428 (2)	C534—H534	0.95
C6—N1	1.338 (2)	C535—C536	1.380 (2)
C2—N2	1.339 (2)	C535—H535	0.95
C5—C51	1.435 (2)	C536—H536	0.95
C51—C52	1.354 (2)	C61—C66	1.383 (2)
C52—C53	1.450 (2)	C61—C62	1.397 (2)
C53—O53	1.242 (2)	C62—C63	1.385 (2)
N6—C6	1.373 (2)	C62—H62	0.95
N2—H2A	0.8602	C63—C64	1.388 (2)
N2—H2B	0.8596	C63—H63	0.95
N6—C61	1.439 (2)	C64—C65	1.389 (2)
N6—C68	1.472 (2)	C65—C66	1.389 (2)
C41—C42	1.504 (3)	C65—H65	0.95
C41—H41A	0.99	C66—H66	0.95
C41—H41B	0.99	C67—H67A	0.98
C42—H42A	0.98	C67—H67B	0.98
C42—H42B	0.98	C67—H67C	0.98
C42—H42C	0.98	C68—H68A	0.98
C51—H51	0.95	C68—H68B	0.98
C52—H52	0.95	C68—H68C	0.98
C4—O4—C41	119.07 (13)	C533—C532—C531	120.30 (16)
C64—O64—C67	117.13 (14)	C533—C532—H532	119.8
C6—N1—C2	116.78 (14)	C531—C532—H532	119.8
C2—N2—H2A	118.4	C532—C533—C534	120.00 (16)
C2—N2—H2B	117.2	C532—C533—H533	120.0
H2A—N2—H2B	120.4	C534—C533—H533	120.0
C4—N3—C2	115.02 (14)	C535—C534—C533	120.06 (16)
C6—N6—C61	123.24 (13)	C535—C534—H534	120.0
C6—N6—C68	117.83 (13)	C533—C534—H534	120.0
C61—N6—C68	114.58 (13)	C536—C535—C534	119.96 (16)
N2—C2—N1	116.76 (15)	C536—C535—H535	120.0
N2—C2—N3	116.91 (15)	C534—C535—H535	120.0
N1—C2—N3	126.30 (15)	C535—C536—C531	120.37 (16)
N3—C4—O4	118.79 (14)	C535—C536—H536	119.8
N3—C4—C5	125.30 (15)	C531—C536—H536	119.8
C5—C4—O4	115.85 (14)	C66—C61—C62	118.89 (15)
C4—C5—C6	113.10 (14)	C66—C61—N6	119.39 (15)
C4—C5—C51	123.54 (15)	C62—C61—N6	121.59 (14)
C6—C5—C51	122.44 (14)	C63—C62—C61	120.40 (15)
N1—C6—N6	114.98 (14)	C63—C62—H62	119.8
N1—C6—C5	122.35 (15)	C61—C62—H62	119.8
N6—C6—C5	122.64 (14)	C62—C63—C64	120.25 (15)
O4—C41—C42	110.51 (14)	C62—C63—H63	119.9
O4—C41—H41A	109.5	C64—C63—H63	119.9
C42—C41—H41A	109.5	C63—C64—O64	116.22 (15)
O4—C41—H41B	109.5	C65—C64—O64	124.14 (15)
C42—C41—H41B	109.5	C63—C64—C65	119.65 (15)
H41A—C41—H41B	108.1	C64—C65—C66	119.81 (16)
C41—C42—H42A	109.5	C64—C65—H65	120.1
C41—C42—H42B	109.5	C66—C65—H65	120.1
H42A—C42—H42B	109.5	C61—C66—C65	120.97 (16)
C41—C42—H42C	109.5	C61—C66—H66	119.5
H42A—C42—H42C	109.5	C65—C66—H66	119.5
H42B—C42—H42C	109.5	O64—C67—H67A	109.5
C52—C51—C5	130.31 (15)	O64—C67—H67B	109.5
C52—C51—H51	114.8	H67A—C67—H67B	109.5
C5—C51—H51	114.8	O64—C67—H67C	109.5
C51—C52—C53	119.94 (15)	H67A—C67—H67C	109.5
C51—C52—H52	120.0	H67B—C67—H67C	109.5
C53—C52—H52	120.0	N6—C68—H68A	109.5
O53—C53—C52	123.30 (15)	N6—C68—H68B	109.5
O53—C53—C531	118.15 (14)	H68A—C68—H68B	109.5
C52—C53—C531	118.52 (14)	N6—C68—H68C	109.5
C532—C531—C536	119.27 (15)	H68A—C68—H68C	109.5
C532—C531—C53	123.04 (15)	H68B—C68—H68C	109.5
C536—C531—C53	117.66 (14)
C6—N1—C2—N2	−173.26 (14)	C51—C5—C6—N6	−17.0 (2)
C6—N1—C2—N3	8.9 (2)	C4—C5—C51—C52	−16.1 (3)
C4—N3—C2—N2	173.24 (15)	O53—C53—C531—C532	152.30 (16)
C4—N3—C2—N1	−9.0 (2)	O53—C53—C531—C536	−25.5 (2)
C2—N3—C4—O4	−177.69 (14)	C52—C53—C531—C536	152.55 (15)
C2—N3—C4—C5	−0.6 (2)	C536—C531—C532—C533	1.2 (2)
C41—O4—C4—C5	−175.14 (14)	C53—C531—C532—C533	−176.58 (15)
N3—C4—C5—C6	8.6 (2)	C531—C532—C533—C534	−1.6 (3)
O4—C4—C5—C6	−174.28 (14)	C532—C533—C534—C535	0.5 (3)
N3—C4—C5—C51	−160.63 (16)	C533—C534—C535—C536	1.1 (3)
O4—C4—C5—C51	16.5 (2)	C534—C535—C536—C531	−1.6 (3)
C2—N1—C6—N6	178.75 (14)	C532—C531—C536—C535	0.4 (2)
C2—N1—C6—C5	0.7 (2)	C53—C531—C536—C535	178.30 (15)
N1—C6—N6—C61	150.48 (15)	C6—N6—C61—C66	141.23 (17)
N1—C6—N6—C68	−4.8 (2)	C68—N6—C61—C66	−62.8 (2)
N3—C4—O4—C41	2.2 (2)	C6—N6—C61—C62	−42.9 (2)
C4—O4—C41—C42	−96.99 (18)	C68—N6—C61—C62	113.07 (18)
C63—C64—O64—C67	−176.96 (16)	C66—C61—C62—C63	1.1 (2)
C6—C5—C51—C52	175.61 (17)	N6—C61—C62—C63	−174.80 (15)
C5—C51—C52—C53	170.18 (16)	C61—C62—C63—C64	0.4 (3)
C51—C52—C53—O53	−5.9 (3)	C67—O64—C64—C65	2.9 (3)
C51—C52—C53—C531	176.08 (15)	C62—C63—C64—O64	178.21 (15)
C52—C53—C531—C532	−29.6 (2)	C62—C63—C64—C65	−1.7 (3)
C61—N6—C6—C5	−31.5 (2)	O64—C64—C65—C66	−178.45 (16)
C68—N6—C6—C5	173.25 (15)	C63—C64—C65—C66	1.4 (3)
C4—C5—C6—N1	−8.5 (2)	C62—C61—C66—C65	−1.3 (3)
C51—C5—C6—N1	160.89 (15)	N6—C61—C66—C65	174.64 (15)
C4—C5—C6—N6	173.61 (14)	C64—C65—C66—C61	0.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O53^i	0.86	2.17	2.9836 (19)	157
N2—H2B···O53^ii	0.86	2.16	2.9806 (19)	160

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