rac-5-Acetyl-6-(4-nitro­phenyl)-6,7-di­hydro-5H-1,3-dioxolo­[4,5-g]­quinoline-8-one: chains of rings built from C—H⋯O and C—H⋯π(arene) hydrogen bonds

Low, J.N.; Cobo, J.; Ortíz, A.; Cuervo, P.; Abonia, R.; Glidewell, C.

doi:10.1107/S1600536804012140

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 60| Part 6| June 2004| Pages o1057-o1059

https://doi.org/10.1107/S1600536804012140

rac-5-Acetyl-6-(4-nitrophenyl)-6,7-dihydro-5H-1,3-dioxolo[4,5-g]quinoline-8-one: chains of rings built from C—H⋯O and C—H⋯π(arene) hydrogen bonds

John N. Low,^a Justo Cobo,^b Angy Ortíz,^c Paola Cuervo,^c Rodrigo Abonia ^c and Christopher Glidewell ^d ^*

^aDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, ^bDepartamento de Química Inorgánica y Orgánica, Universidad de Jaén, 23071 Jaén, Spain, ^cGrupo de Investigación de Compuestos Heterociclícos, Departamento de Química, Universidad de Valle, AA 25360 Colombia, and ^dSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland
^*Correspondence e-mail: cg@st-andrews.ac.uk

(Received 17 May 2004; accepted 19 May 2004; online 22 May 2004)

Molecules of the title compound, C₁₈H₁₄N₂O₆, are linked into chains by a combination of one C—H⋯O and one C—H⋯π(arene) hydrogen bond, augmented by a dipolar carbonyl–carbonyl interaction.

Comment

The title compound, (I), was prepared as an intermediate in the preparation of new bis-amides derived from tetrahydroquinolones, for use as model compounds for DNA intercalating agents (Gamage et al., 1999 ; Chacón-García & Martínez, 2001 ; Deady et al., 2001 ).

Compound (I) (Fig. 1) crystallizes in the polar space group Pna2₁. The molecule contains a stereogenic centre at C6, and the selected reference molecule is of S configuration; however, the space group accommodates equal numbers of R and S enantiomers.

For the heterocyclic ring (N5/C4A/C8A/C8/C7/C6), the ring-puckering parameters (Cremer & Pople, 1975 ) for this atom sequence, θ = 124.7 (3)° and φ = 120.3 (4)°, indicate an almost pure envelope form (Evans & Boeyens, 1989 ). The inter-bond angles at N5 (Table 1) indicate that this atom has effectively planar coordination, as expected for amidic N, but, unexpectedly, the nitrophenyl substituent at C6 occupies an axial site. Within the fused-ring system, the bond lengths (Table 1) show several unexpected features. In particular, the bonds C3A—C4 and C9—C9A are significantly shorter than the other bonds in the carbocyclic aromatic ring, and the bond C4A—N5 is very long for its type: the mean value for bonds of this type (Allen et al., 1987 ) is 1.371 Å. It may also be noted that the two carbonyl C=O distances are identical, despite their different local environments.

The molecules of (I) are linked into chains by a combination of C—H⋯O and C—H⋯π(arene) hydrogen bonds, augmented by a dipolar carbonyl–carbonyl interaction. Atoms C62 and C63 in the molecule at (x, y, z) act as hydrogen-bond donors, respectively, to amidic atom O51 and to the ring C61—C66, both in the molecule at ( $[1\over2]$ + x, $[3\over2]$ − y, z), and propagation of these interactions produces a chain of rings running parallel to the [100] direction and generated by the a glide plane at y = 0.75 (Fig. 2). In addition, carbonyl atom O51 in the molecule at (x, y, z) forms a short contact with the carbonyl atom C51 in the molecule at (x − $[1\over2]$ , $[3\over2]$ − y, z): the O⋯C distance is 3.001 (3) Å, the C—O⋯C angle is 150 (4)° and the O⋯C—O angle is 87.4 (2)°, indicative of a type I interaction (Allen et al., 1998 ), which reinforces the [100] chain.

Two antiparallel chains of this type pass through each unit cell, generated by the a glide planes at y = 0.25 and 0.75, but there are no direction-specific interactions between adjacent chains. In particular, there are no π–π stacking interaction and no C—H⋯O hydrogen bonds involving the nitro O atoms.

Figure 1
The S enantiomer of compound (I

), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Figure 2
Stereoview of part of the crystal structure of compound (I

), showing the formation of a hydrogen-bonded chain along [100].

Experimental

A mixture of 6-(4-nitrophenyl)-6,7-dihydro-5H-[1,3]dioxolo[4,5-g]quinolin-8-one (250 mg, 0.71 mmol) (Donnelly & Farell, 1990 ) and acetic anhydride (3 ml) was heated at 353 K for 90 min. After reaction was complete (as shown by thin-layer chromatography), the solvent was removed under vacuum and the resulting solid was washed with water and then purified by column chromatography on silica gel with chloroform–ethyl acetate (9:1 v/v) as eluant, to give a pale yellow solid (60% yield, m.p. 483 K). MS (70 eV): m/e (%) 354 (40, M⁺), 312 (86), 190 (39), 43 (100). Crystals suitable for single-crystal X-ray diffraction were grown from a solution in 96% aqueous ethanol.

Crystal data

C₁₈H₁₄N₂O₆
M_r = 354.31
Orthorhombic, Pna2₁
a = 6.5253 (2) Å
b = 21.4286 (5) Å
c = 10.8198 (9) Å
V = 1512.91 (14) Å³
Z = 4
D_x = 1.556 Mg m⁻³
Mo Kα radiation
Cell parameters from 1952 reflections
θ = 3.3–27.1°
μ = 0.12 mm⁻¹
T = 120 (2) K
Needle, colourless
0.30 × 0.10 × 0.09 mm

Data collection

Nonius KappaCCD diffractometer
φ scans, and ω scans with κ offsets
Absorption correction: multi-scan (SORTAV; Blessing, 1995 , 1997 ) T_min = 0.956, T_max = 0.989
15335 measured reflections
1762 independent reflections
1360 reflections with I > 2σ(I)
R_int = 0.082
θ_max = 27.1°
h = −8 → 7
k = −27 → 27
l = −13 → 13

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.087
S = 1.06
1762 reflections
237 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0457P)² + 0.0405P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.22 e Å⁻³
Extinction correction: SHELXL97
Extinction coefficient: 0.0110 (18)

Table 1
Selected geometric parameters (Å, °)

O1—C2	1.431 (4)
C2—O3	1.440 (4)
O3—C3A	1.367 (3)
C3A—C4	1.369 (4)
C4—C4A	1.400 (4)
C4A—N5	1.425 (3)
N5—C6	1.472 (4)
C6—C7	1.527 (4)
C7—C8	1.506 (4)
C8—C8A	1.480 (4)
C8A—C9	1.407 (4)
C9—C9A	1.352 (4)
C9A—O1	1.381 (3)
C3A—C9A	1.385 (4)
C4A—C8A	1.403 (4)
N5—C51	1.388 (4)
C51—O51	1.223 (3)
C8—O8	1.223 (4)

C51—N5—C4A	125.0 (2)
C51—N5—C6	118.1 (2)
C4A—N5—C6	115.1 (2)

Table 2
Hydrogen-bonding geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C62—H62⋯O51ⁱ	0.95	2.48	3.358 (4)	153
C63—H63⋯Cg1ⁱ	0.95	2.98	3.693 (3)	132
Symmetry code: (i) $[{\script{1\over 2}}+x,{\script{3\over 2}}-y,z]$ . Cg1 is the centroid of ring C61–C66

All H atoms were located in difference maps and subsequently treated as riding atoms, with distances C—H = 0.95 (aromatic), 0.98 (methyl), 0.99 (CH₂) or 1.00 Å (aliphatic CH), and with U_iso(H) = 1.2U_eq(C), or 1.5U_eq(C) for the methyl group. The value of the Flack parameter [0.2 (13); Flack, 1983 ] was indeterminate (Flack & Bernardinelli, 2000 ), and hence the correct orientation of the structure relative to the polar axis direction could not be established (Jones, 1986 ). Accordingly, the Friedel-equivalent reflections were merged prior to the final refinement.

Data collection: KappaCCD Server Software (Nonius, 1997 ); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997 ); data reduction: DENZO–SMN; program(s) used to solve structure: OSCAIL (McArdle, 2003 ) and SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536804012140/lh6221sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536804012140/lh6221Isup2.hkl

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

rac-5-Acetyl-6-(4-nitrophenyl)-6,7-dihydro-5H-1,3-dioxolo[4,5-g]quinoline-8-one top

Crystal data top

C₁₈H₁₄N₂O₆	F(000) = 736
M_r = 354.31	D_x = 1.556 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 1952 reflections
a = 6.5253 (2) Å	θ = 3.3–27.1°
b = 21.4286 (5) Å	µ = 0.12 mm⁻¹
c = 10.8198 (9) Å	T = 120 K
V = 1512.91 (14) Å³	Plate, colourless
Z = 4	0.30 × 0.10 × 0.09 mm

Data collection top

Nonius KappaCCD diffractometer	1762 independent reflections
Radiation source: rotating anode	1360 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.082
φ scans, and ω scans with κ offsets	θ_max = 27.1°, θ_min = 3.3°
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997)	h = −8→7
T_min = 0.956, T_max = 0.989	k = −27→27
15335 measured reflections	l = −13→13

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.087	w = 1/[σ²(F_o²) + (0.0457P)² + 0.0405P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
1762 reflections	Δρ_max = 0.21 e Å⁻³
237 parameters	Δρ_min = −0.22 e Å⁻³
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0110 (18)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.5209 (4)	0.45991 (10)	0.5921 (2)	0.0450 (6)
C2	0.6518 (5)	0.49285 (15)	0.5084 (4)	0.0429 (8)
O3	0.5919 (3)	0.55753 (10)	0.5100 (2)	0.0383 (6)
C3A	0.4110 (4)	0.55944 (14)	0.5736 (3)	0.0278 (7)
C4	0.2903 (4)	0.61069 (13)	0.5940 (3)	0.0265 (6)
C4A	0.1148 (4)	0.60062 (12)	0.6658 (2)	0.0237 (6)
N5	−0.0191 (3)	0.65140 (12)	0.6922 (2)	0.0262 (5)
C51	−0.1005 (4)	0.69175 (13)	0.6047 (3)	0.0291 (7)
O51	−0.2149 (3)	0.73380 (10)	0.63757 (19)	0.0426 (6)
C52	−0.0541 (5)	0.68171 (14)	0.4710 (3)	0.0313 (7)
C6	−0.1136 (4)	0.65011 (13)	0.8158 (3)	0.0278 (6)
C61	0.0432 (4)	0.65684 (13)	0.9186 (3)	0.0249 (6)
C62	0.2377 (4)	0.68212 (13)	0.8979 (3)	0.0268 (6)
C63	0.3740 (4)	0.69024 (13)	0.9951 (3)	0.0273 (6)
C64	0.3144 (4)	0.67328 (12)	1.1127 (2)	0.0246 (6)
N64	0.4578 (4)	0.68102 (11)	1.2154 (2)	0.0298 (6)
O41	0.3963 (3)	0.67045 (11)	1.3207 (2)	0.0451 (6)
O42	0.6331 (3)	0.69795 (11)	1.1920 (2)	0.0410 (6)
C65	0.1243 (4)	0.64875 (13)	1.1358 (3)	0.0292 (7)
C66	−0.0106 (4)	0.64056 (13)	1.0388 (3)	0.0306 (7)
C7	−0.2388 (4)	0.59007 (15)	0.8248 (3)	0.0358 (7)
C8	−0.1070 (5)	0.53365 (14)	0.8006 (3)	0.0347 (7)
O8	−0.1483 (4)	0.48271 (11)	0.8451 (2)	0.0578 (8)
C8A	0.0733 (4)	0.54239 (13)	0.7194 (3)	0.0278 (6)
C9	0.2061 (5)	0.49165 (13)	0.6998 (3)	0.0327 (7)
C9A	0.3695 (4)	0.50171 (13)	0.6255 (3)	0.0307 (7)
H2A	0.6375	0.4756	0.4239	0.051*
H2B	0.7966	0.4886	0.5344	0.051*
H4	0.3235	0.6506	0.5614	0.032*
H52A	−0.1760	0.6913	0.4216	0.047*
H52B	−0.0145	0.6381	0.4577	0.047*
H52C	0.0586	0.7092	0.4460	0.047*
H6	−0.2106	0.6861	0.8215	0.033*
H62	0.2769	0.6939	0.8166	0.032*
H63	0.5064	0.7072	0.9807	0.033*
H65	0.0859	0.6375	1.2175	0.035*
H66	−0.1425	0.6235	1.0544	0.037*
H7A	−0.2999	0.5868	0.9083	0.043*
H7B	−0.3519	0.5914	0.7639	0.043*
H9	0.1822	0.4522	0.7369	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0547 (14)	0.0436 (13)	0.0369 (12)	0.0229 (12)	0.0026 (11)	−0.0028 (11)
C2	0.0360 (17)	0.046 (2)	0.047 (2)	0.0074 (15)	0.0007 (16)	−0.0128 (17)
O3	0.0296 (11)	0.0476 (13)	0.0378 (13)	0.0056 (9)	0.0066 (10)	−0.0047 (10)
C3A	0.0234 (15)	0.0373 (17)	0.0226 (16)	0.0023 (12)	−0.0028 (11)	−0.0051 (12)
C4	0.0256 (14)	0.0304 (15)	0.0235 (15)	−0.0023 (12)	−0.0032 (11)	0.0008 (12)
C4A	0.0238 (14)	0.0286 (14)	0.0188 (14)	0.0023 (12)	−0.0033 (11)	−0.0020 (11)
N5	0.0261 (12)	0.0312 (12)	0.0212 (12)	0.0050 (10)	0.0008 (10)	0.0007 (10)
C51	0.0289 (16)	0.0326 (16)	0.0258 (16)	0.0017 (13)	−0.0048 (12)	−0.0009 (13)
O51	0.0499 (13)	0.0473 (13)	0.0306 (12)	0.0214 (11)	−0.0031 (11)	−0.0018 (11)
C52	0.0350 (18)	0.0357 (17)	0.0230 (15)	0.0031 (13)	−0.0029 (12)	0.0026 (13)
C6	0.0272 (15)	0.0352 (15)	0.0211 (14)	0.0055 (12)	0.0016 (12)	−0.0010 (13)
C61	0.0288 (16)	0.0245 (14)	0.0213 (15)	0.0028 (12)	0.0012 (12)	−0.0011 (12)
C62	0.0303 (16)	0.0296 (15)	0.0206 (13)	0.0000 (12)	0.0026 (11)	0.0010 (12)
C63	0.0267 (15)	0.0276 (15)	0.0277 (16)	0.0009 (12)	0.0026 (12)	0.0029 (12)
C64	0.0291 (15)	0.0248 (14)	0.0199 (15)	0.0015 (11)	−0.0017 (12)	−0.0023 (12)
N64	0.0297 (14)	0.0332 (14)	0.0265 (14)	−0.0014 (11)	−0.0012 (11)	0.0013 (11)
O41	0.0463 (14)	0.0687 (16)	0.0204 (12)	−0.0099 (11)	−0.0024 (11)	0.0060 (11)
O42	0.0290 (12)	0.0580 (14)	0.0360 (13)	−0.0080 (10)	−0.0031 (10)	0.0002 (11)
C65	0.0322 (16)	0.0363 (16)	0.0192 (15)	−0.0025 (13)	0.0036 (13)	0.0019 (13)
C66	0.0296 (16)	0.0363 (17)	0.0259 (15)	−0.0023 (12)	0.0028 (12)	−0.0013 (13)
C7	0.0278 (15)	0.058 (2)	0.0216 (14)	−0.0085 (14)	0.0020 (13)	−0.0019 (15)
C8	0.0430 (19)	0.0398 (18)	0.0214 (16)	−0.0138 (14)	0.0013 (13)	−0.0032 (14)
O8	0.0848 (19)	0.0412 (14)	0.0474 (16)	−0.0206 (13)	0.0283 (14)	−0.0019 (13)
C8A	0.0324 (16)	0.0309 (16)	0.0201 (14)	−0.0057 (12)	−0.0012 (12)	−0.0024 (12)
C9	0.0469 (18)	0.0242 (15)	0.0270 (17)	−0.0016 (13)	0.0005 (15)	−0.0001 (13)
C9A	0.0389 (17)	0.0291 (15)	0.0242 (17)	0.0080 (13)	−0.0068 (14)	−0.0056 (13)

Geometric parameters (Å, º) top

O1—C2	1.431 (4)	C9—C9A	1.352 (4)
C2—O3	1.440 (4)	C9—H9	0.95
C2—H2A	0.99	C9A—O1	1.381 (3)
C2—H2B	0.99	C3A—C9A	1.385 (4)
O3—C3A	1.367 (3)	C4A—C8A	1.403 (4)
C3A—C4	1.369 (4)	N5—C51	1.388 (4)
C4—C4A	1.400 (4)	C51—O51	1.223 (3)
C4—H4	0.95	C8—O8	1.223 (4)
C4A—N5	1.425 (3)	C61—C66	1.391 (4)
N5—C6	1.472 (4)	C61—C62	1.398 (4)
C51—C52	1.493 (4)	C62—C63	1.388 (4)
C52—H52A	0.98	C62—H62	0.95
C52—H52B	0.98	C63—C64	1.379 (4)
C52—H52C	0.98	C63—H63	0.95
C6—C61	1.519 (4)	C64—C65	1.370 (4)
C6—C7	1.527 (4)	C64—N64	1.463 (4)
C6—H6	1.00	N64—O42	1.226 (3)
C7—C8	1.506 (4)	N64—O41	1.229 (3)
C7—H7A	0.99	C65—C66	1.381 (4)
C7—H7B	0.99	C65—H65	0.95
C8—C8A	1.480 (4)	C66—H66	0.95
C8A—C9	1.407 (4)

C9A—O1—C2	105.8 (2)	C62—C61—C6	122.1 (2)
O1—C2—O3	107.8 (2)	C63—C62—C61	120.6 (3)
O1—C2—H2A	110.2	C63—C62—H62	119.7
O3—C2—H2A	110.2	C61—C62—H62	119.7
O1—C2—H2B	110.2	C64—C63—C62	119.0 (3)
O3—C2—H2B	110.2	C64—C63—H63	120.5
H2A—C2—H2B	108.5	C62—C63—H63	120.5
C3A—O3—C2	105.6 (2)	C65—C64—C63	121.7 (3)
O3—C3A—C4	127.0 (3)	C65—C64—N64	118.9 (2)
O3—C3A—C9A	110.2 (2)	C63—C64—N64	119.4 (2)
C4—C3A—C9A	122.6 (3)	O42—N64—O41	123.4 (3)
C3A—C4—C4A	115.8 (3)	O42—N64—C64	118.3 (2)
C3A—C4—H4	122.1	O41—N64—C64	118.3 (2)
C4A—C4—H4	122.1	C64—C65—C66	119.1 (2)
C4—C4A—C8A	121.6 (2)	C64—C65—H65	120.4
C4—C4A—N5	119.7 (2)	C66—C65—H65	120.4
C8A—C4A—N5	118.5 (2)	C65—C66—C61	121.2 (3)
C51—N5—C4A	125.0 (2)	C65—C66—H66	119.4
C51—N5—C6	118.1 (2)	C61—C66—H66	119.4
C4A—N5—C6	115.1 (2)	C8—C7—C6	111.1 (2)
O51—C51—N5	119.6 (3)	C8—C7—H7A	109.4
O51—C51—C52	120.8 (3)	C6—C7—H7A	109.4
N5—C51—C52	119.6 (2)	C8—C7—H7B	109.4
C51—C52—H52A	109.5	C6—C7—H7B	109.4
C51—C52—H52B	109.5	H7A—C7—H7B	108.0
H52A—C52—H52B	109.5	O8—C8—C8A	121.4 (3)
C51—C52—H52C	109.5	O8—C8—C7	121.5 (3)
H52A—C52—H52C	109.5	C8A—C8—C7	117.1 (2)
H52B—C52—H52C	109.5	C4A—C8A—C9	120.4 (3)
N5—C6—C61	112.4 (2)	C4A—C8A—C8	120.8 (3)
N5—C6—C7	107.3 (2)	C9—C8A—C8	118.8 (3)
C61—C6—C7	113.2 (2)	C9A—C9—C8A	116.9 (3)
N5—C6—H6	107.9	C9A—C9—H9	121.6
C61—C6—H6	107.9	C8A—C9—H9	121.6
C7—C6—H6	107.9	C9—C9A—O1	128.0 (3)
C66—C61—C62	118.4 (3)	C9—C9A—C3A	122.5 (3)
C66—C61—C6	119.4 (2)	O1—C9A—C3A	109.5 (3)

C9A—O1—C2—O3	9.3 (3)	C63—C64—N64—O42	−5.6 (4)
O1—C2—O3—C3A	−10.7 (3)	C65—C64—N64—O41	−6.4 (4)
C2—O3—C3A—C4	−176.6 (3)	C63—C64—N64—O41	174.2 (3)
C2—O3—C3A—C9A	8.0 (3)	C63—C64—C65—C66	0.3 (4)
O3—C3A—C4—C4A	−178.0 (3)	N64—C64—C65—C66	−179.1 (2)
C9A—C3A—C4—C4A	−3.1 (4)	C64—C65—C66—C61	−0.1 (4)
C3A—C4—C4A—C8A	3.8 (4)	C62—C61—C66—C65	−0.3 (4)
C3A—C4—C4A—N5	179.6 (2)	C6—C61—C66—C65	−176.9 (3)
C4—C4A—N5—C51	51.2 (4)	N5—C6—C7—C8	56.7 (3)
C8A—C4A—N5—C51	−132.8 (3)	C61—C6—C7—C8	−67.9 (3)
C4—C4A—N5—C6	−144.3 (3)	C6—C7—C8—O8	152.7 (3)
C8A—C4A—N5—C6	31.7 (3)	C6—C7—C8—C8A	−28.0 (4)
C4A—N5—C51—O51	179.7 (3)	C4—C4A—C8A—C9	−1.5 (4)
C6—N5—C51—O51	15.7 (4)	N5—C4A—C8A—C9	−177.4 (3)
C4A—N5—C51—C52	2.2 (4)	C4—C4A—C8A—C8	176.6 (3)
C6—N5—C51—C52	−161.9 (3)	N5—C4A—C8A—C8	0.7 (4)
C51—N5—C6—C61	−129.5 (3)	O8—C8—C8A—C4A	177.9 (3)
C4A—N5—C6—C61	64.8 (3)	C7—C8—C8A—C4A	−1.5 (4)
C51—N5—C6—C7	105.4 (3)	O8—C8—C8A—C9	−3.9 (4)
C4A—N5—C6—C7	−60.2 (3)	C7—C8—C8A—C9	176.7 (3)
N5—C6—C61—C66	−163.4 (2)	C4A—C8A—C9—C9A	−1.5 (4)
C7—C6—C61—C66	−41.6 (4)	C8—C8A—C9—C9A	−179.7 (3)
N5—C6—C61—C62	20.1 (4)	C8A—C9—C9A—O1	179.9 (3)
C7—C6—C61—C62	141.9 (3)	C8A—C9—C9A—C3A	2.2 (4)
C66—C61—C62—C63	0.5 (4)	C2—O1—C9A—C9	177.5 (3)
C6—C61—C62—C63	177.0 (3)	C2—O1—C9A—C3A	−4.5 (3)
C61—C62—C63—C64	−0.3 (4)	O3—C3A—C9A—C9	175.8 (3)
C62—C63—C64—C65	−0.1 (4)	C4—C3A—C9A—C9	0.2 (4)
C62—C63—C64—N64	179.3 (2)	O3—C3A—C9A—O1	−2.3 (3)
C65—C64—N64—O42	173.8 (2)	C4—C3A—C9A—O1	−177.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C62—H62···O51ⁱ	0.95	2.48	3.358 (4)	153
C63—H63···Cg1ⁱ	0.95	2.98	3.693 (3)	132

Symmetry code: (i) x+1/2, −y+3/2, z.

Acknowledgements

X-ray data were collected at the EPSRC X-ray Crystallographic Service, University of Southampton, England; the authors thank the staff for all their help and advice. JNL thanks NCR Self-Service, Dundee, for grants which have provided computing facilities for this work. JC thanks the Consejería de Educación y Ciencia (Junta de Andalucía, Spain) and the Universidad de Jaén for financial support; RA thanks Fundación para la Promoción de la Investigación y la Tecnología (Banco de la República) and Universidad del Valle for financial support. PC thanks COLCIENCIAS for a doctoral fellowship.

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