6-(2-Hydroxy­benzo­yl)-2-(4-methyl­phen­yl)-5-methyl-7-phenyl­pyrazolo[1,5-a]pyrimidine: complex sheets built from C—H⋯N and C—H⋯O hydrogen bonds

Portilla, J.; Torre, J.M. de la; Cobo, J.; Low, J.N.; Glidewell, C.

doi:10.1107/S1600536806025220

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 62| Part 8| August 2006| Pages o3195-o3197

https://doi.org/10.1107/S1600536806025220

6-(2-Hydroxybenzoyl)-2-(4-methylphenyl)-5-methyl-7-phenylpyrazolo[1,5-a]pyrimidine: complex sheets built from C—H⋯N and C—H⋯O hydrogen bonds

Jaime Portilla,^a José M. de la Torre,^b Justo Cobo,^b John N. Low ^c and Christopher Glidewell ^d ^*

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

(Received 29 June 2006; accepted 29 June 2006; online 6 July 2006)

The molecules of the title compound, C₂₇H₂₁N₃O₂, contain an intramolecular O—H⋯O hydrogen bond, and they are linked into complex sheets by a combination of two C—H⋯N hydrogen bonds and two C—H⋯O hydrogen bonds.

Comment

We report here the structure of the title new pyrazolo[1,5-a]pyrimidine, (I) (Fig. 1), prepared under solvent-free conditions from the reaction between a 5-aminopyrazole and a 2-benzoylchromone.

The bond distances in the pyrazolo[1,5-a]pyrimidine fragment (Table 1) are typical of this ring system (Portilla et al., 2005 , 2006 ) and they are consistent with 10-π electron delocalization reminiscent of the naphthalene type. The aryl ring at C2 is almost coplanar with the heterocyclic system, but the substituents at C6 and C7 are considerably twisted out of this plane, probably to avoid mutually repulsive interactions between their aryl rings (Table 1).

There is a fairly short intramolecular O—H⋯O hydrogen bond, but the supramolecular aggregation of (I) depends solely on rather long, and thus fairly weak, C—H⋯N and C—H⋯O hydrogen bonds (Table 2), which link the molecules into complex sheets. The formation of the sheet can be readily analysed in terms of its simple sub-structures.

Aryl atom C74 in the molecule at (x, y, z) acts as hydrogen-bond donor to hydroxyl atom O62 in the molecule at (1 − x, −y, 1 − z), so generating by inversion a centrosymmetric R₂²(22) (Bernstein et al., 1995 ) dimer centred at ( $[{1\over 2}]$ , 0, $[{1\over 2}]$ ) (Fig. 2), and these dimers are linked by the C—H⋯N hydrogen bonds. Atoms C3 and C22 in the molecule at (x, y, z) and (1 − x, −y, 1 − z) both act as hydrogen-bond donors to the atoms N4 in the molecules at ( $[{3\over 2}]$ − x, $[{1\over 2}]$ + y, $[{3\over 2}]$ − z) and (− $[{1\over 2}]$ + x, − $[{1\over 2}]$ − y, − $[{1\over 2}]$ + z), which themselves lie in the R₂²(22) dimers centred at (1, $[{1\over 2}]$ , 1) and (0, − $[{1\over 2}]$ , 0), respectively. Propagation of these hydrogen bonds then generates a chain of rings along [111], in which R₂²(22) rings alternate with R₂¹(7) rings (Fig. 3).

Finally, aryl atom C76 in the molecule at (x, y, z) acts as hydrogen-bond donor to carbonyl atom O67 in the molecule at (x, 1 + y, z), so generating by translation a C(7) chain running parallel to the [010] direction. The combination of [010] and [111] chains generates a sheet parallel to (10 $[\overline{1}]$ ), but there are no direction-specific interactions between adjacent sheets.

Figure 1
The molecular structure of compound (I)

, showing the atom-labelling scheme and the intramolecular O—H⋯O hydrogen bond (dashed line). Displacement ellipsoids are drawn at the 30% probability level.

Figure 2
Part of the crystal structure of compound (I)

, showing the formation of an R₂²(22) dimer. For the sake of clarity, H atoms bonded to C atoms but not involved in the motifs shown have been omitted. Similarly, the unit-cell outline has been omitted. Atoms marked with an asterisk (*) are at the symmetry position (1 − x, −y, 1 − z).

Figure 3
A stereoscopic view of part of the crystal structure of compound (I)

, showing the formation of a chain of rings along [111]. For the sake of clarity, H atoms bonded to C atoms but not involved in the motifs shown have been omitted.

Experimental

Equimolar quantities (1.0 mmol of each component) of 3-(4-methylphenyl)-5-amino-1H-pyrazole and 3-benzoyl-2-methylbenzo-4-pyrone were placed in an open Pyrex glass vessel and heated in an oil-bath at 373 K for 2 min. The reaction mixture was then cooled and extracted with ethanol. After removal of the solvent, the product, (I), was recrystallized from dimethylformamide to give yellow crystals suitable for single-crystal X-ray diffraction (m.p. 471—473 K, yield 60%).

Crystal data

C₂₇H₂₁N₃O₂
M_r = 419.47
Monoclinic, C 2/c
a = 38.7649 (11) Å
b = 6.7864 (2) Å
c = 16.7002 (5) Å
β = 108.599 (2)°
V = 4163.9 (2) Å³
Z = 8
D_x = 1.338 Mg m⁻³
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 120 (2) K
Lath, yellow
0.80 × 0.50 × 0.20 mm

Data collection

Bruker Nonius KappaCCD area-detector diffractometer
φ and ω scans
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.964, T_max = 0.983
30599 measured reflections
4751 independent reflections
3797 reflections with I > 2σ(I)
R_int = 0.036
θ_max = 27.5°

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.121
S = 1.02
4751 reflections
291 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0575P)² + 3.7732P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.001
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

N1—C2	1.3505 (18)
C2—C3	1.4013 (19)
C3—C3A	1.377 (2)
C3A—N4	1.3525 (18)
N4—C5	1.3141 (18)
C5—C6	1.4342 (19)
C6—C7	1.376 (2)
C7—N7A	1.3675 (18)
N7A—N1	1.3603 (16)
C3A—N7A	1.4011 (17)

N1—C2—C21—C22	179.38 (13)
C5—C6—C67—C61	−110.80 (15)
C6—C67—C61—C62	−176.77 (13)
C6—C7—C71—C72	43.8 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O62—H62⋯O67	0.96	1.68	2.554 (2)	150
C3—H3⋯N4ⁱ	0.95	2.61	3.543 (2)	168
C22—H22⋯N4ⁱ	0.95	2.57	3.513 (2)	174
C74—H74⋯O62ⁱⁱ	0.95	2.55	3.422 (2)	154
C76—H76⋯O67ⁱⁱⁱ	0.95	2.56	3.444 (2)	155
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x+1, -y, -z+1; (iii) x, y+1, z.

All H atoms were located in a difference map and then treated as riding, with C—H distances of 0.95 (aromatic) or 0.98 Å (methyl) and an O—H distance of 0.96 Å, and with U_iso(H) = xU_eq(C,O), where x = 1.5 for the methyl groups and 1.2 for all other H.

Data collection: COLLECT (Nonius, 1999 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; 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 and PRPKAPPA (Ferguson, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536806025220/lh2121sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536806025220/lh2121Isup2.hkl

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; 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 and PRPKAPPA (Ferguson, 1999).

6-(2-Hydroxybenzoyl)-2-(4-methylphenyl)-5-methyl-7- phenylpyrazolo[1,5-a]pyrimidine top

Crystal data top

C₂₇H₂₁N₃O₂	F(000) = 1760
M_r = 419.47	D_x = 1.338 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4751 reflections
a = 38.7649 (11) Å	θ = 2.5–27.5°
b = 6.7864 (2) Å	µ = 0.09 mm⁻¹
c = 16.7002 (5) Å	T = 120 K
β = 108.599 (2)°	Lath, yellow
V = 4163.9 (2) Å³	0.80 × 0.50 × 0.20 mm
Z = 8

Data collection top

Bruker Nonius KappaCCD area-detector diffractometer	4751 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	3797 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 2.5°
φ and ω scans	h = −50→50
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −8→8
T_min = 0.964, T_max = 0.983	l = −20→21
30599 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0575P)² + 3.7732P] where P = (F_o² + 2F_c²)/3
4751 reflections	(Δ/σ)_max = 0.001
291 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Special details top

Experimental. MS (70 eV) m/z (%): 420 (29), 419 (89, M⁺), 418 (40), 404 (19), 298 (42), 299 (100), 300 (23), 77 (19), 39 (29).

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

	x	y	z	U_iso*/U_eq
N1	0.64536 (3)	0.64378 (18)	0.73713 (7)	0.0241 (3)
C2	0.67725 (4)	0.7409 (2)	0.76857 (8)	0.0225 (3)
C21	0.67888 (4)	0.9261 (2)	0.81559 (8)	0.0228 (3)
C22	0.71209 (4)	1.0247 (2)	0.84866 (9)	0.0277 (3)
C23	0.71402 (4)	1.2014 (2)	0.89185 (9)	0.0289 (3)
C24	0.68331 (4)	1.2854 (2)	0.90335 (9)	0.0282 (3)
C241	0.68582 (5)	1.4727 (2)	0.95313 (11)	0.0382 (4)
C25	0.65025 (4)	1.1876 (2)	0.86945 (10)	0.0299 (3)
C26	0.64783 (4)	1.0101 (2)	0.82675 (9)	0.0268 (3)
C3	0.70596 (4)	0.6500 (2)	0.74876 (9)	0.0238 (3)
C3A	0.69070 (4)	0.4875 (2)	0.70129 (8)	0.0226 (3)
N4	0.70502 (3)	0.34454 (17)	0.66512 (7)	0.0234 (3)
C5	0.68290 (4)	0.2098 (2)	0.62001 (9)	0.0240 (3)
C51	0.69940 (4)	0.0567 (2)	0.57839 (10)	0.0310 (3)
C6	0.64457 (4)	0.2128 (2)	0.60786 (9)	0.0240 (3)
C67	0.62121 (4)	0.0628 (2)	0.54968 (9)	0.0267 (3)
O67	0.62591 (3)	−0.11379 (16)	0.56964 (7)	0.0373 (3)
C61	0.59523 (4)	0.1220 (2)	0.46813 (9)	0.0257 (3)
C62	0.57220 (4)	−0.0213 (2)	0.41643 (10)	0.0304 (3)
O62	0.57228 (3)	−0.21027 (18)	0.44091 (8)	0.0421 (3)
C63	0.54909 (4)	0.0291 (3)	0.33721 (10)	0.0380 (4)
C64	0.54886 (4)	0.2187 (3)	0.30835 (10)	0.0404 (4)
C65	0.57112 (5)	0.3631 (3)	0.35764 (10)	0.0365 (4)
C66	0.59382 (4)	0.3147 (2)	0.43721 (10)	0.0299 (3)
C7	0.63000 (4)	0.3528 (2)	0.64733 (8)	0.0235 (3)
C71	0.59079 (4)	0.3629 (2)	0.63969 (9)	0.0262 (3)
C72	0.57238 (4)	0.1894 (3)	0.64525 (9)	0.0323 (4)
C73	0.53492 (4)	0.1940 (3)	0.62985 (11)	0.0398 (4)
C74	0.51589 (4)	0.3687 (3)	0.60952 (11)	0.0413 (4)
C75	0.53420 (4)	0.5409 (3)	0.60536 (10)	0.0378 (4)
C76	0.57165 (4)	0.5397 (2)	0.62136 (9)	0.0308 (3)
N7A	0.65374 (3)	0.48960 (18)	0.69467 (7)	0.0226 (3)
H22	0.7335	0.9704	0.8415	0.033*
H23	0.7368	1.2661	0.9140	0.035*
H24A	0.6830	1.4424	1.0081	0.057*
H24B	0.6665	1.5633	0.9220	0.057*
H24C	0.7096	1.5342	0.9618	0.057*
H25	0.6288	1.2439	0.8757	0.036*
H26	0.6250	0.9456	0.8050	0.032*
H3	0.7306	0.6916	0.7647	0.029*
H51A	0.7248	0.0911	0.5860	0.046*
H51B	0.6857	0.0512	0.5179	0.046*
H51C	0.6984	−0.0722	0.6040	0.046*
H62	0.5916	−0.2188	0.4937	0.051*
H63	0.5334	−0.0671	0.3029	0.046*
H64	0.5332	0.2518	0.2536	0.049*
H65	0.5707	0.4937	0.3368	0.044*
H66	0.6087	0.4135	0.4716	0.036*
H72	0.5853	0.0688	0.6595	0.039*
H73	0.5223	0.0758	0.6334	0.048*
H74	0.4903	0.3705	0.5984	0.050*
H75	0.5211	0.6611	0.5914	0.045*
H76	0.5842	0.6593	0.6198	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0206 (6)	0.0306 (7)	0.0204 (6)	−0.0027 (5)	0.0057 (5)	−0.0040 (5)
C2	0.0190 (6)	0.0288 (8)	0.0174 (6)	−0.0027 (5)	0.0025 (5)	0.0012 (5)
C21	0.0218 (7)	0.0275 (7)	0.0181 (6)	−0.0007 (5)	0.0050 (5)	0.0022 (5)
C22	0.0221 (7)	0.0317 (8)	0.0291 (8)	−0.0020 (6)	0.0081 (6)	−0.0024 (6)
C23	0.0271 (7)	0.0288 (8)	0.0292 (8)	−0.0056 (6)	0.0068 (6)	−0.0021 (6)
C24	0.0346 (8)	0.0262 (8)	0.0239 (7)	0.0012 (6)	0.0095 (6)	0.0030 (6)
C241	0.0461 (10)	0.0320 (9)	0.0365 (9)	0.0011 (7)	0.0133 (7)	−0.0048 (7)
C25	0.0274 (8)	0.0332 (8)	0.0294 (8)	0.0064 (6)	0.0098 (6)	0.0026 (6)
C26	0.0207 (7)	0.0321 (8)	0.0258 (7)	−0.0006 (6)	0.0050 (6)	0.0010 (6)
C3	0.0182 (6)	0.0293 (8)	0.0218 (7)	−0.0030 (5)	0.0036 (5)	−0.0003 (6)
C3A	0.0172 (6)	0.0298 (8)	0.0195 (6)	−0.0008 (5)	0.0041 (5)	0.0020 (6)
N4	0.0202 (6)	0.0261 (6)	0.0222 (6)	−0.0001 (5)	0.0043 (5)	−0.0001 (5)
C5	0.0226 (7)	0.0266 (7)	0.0202 (7)	0.0003 (6)	0.0034 (5)	0.0034 (6)
C51	0.0279 (8)	0.0296 (8)	0.0334 (8)	0.0012 (6)	0.0069 (6)	−0.0055 (6)
C6	0.0218 (7)	0.0271 (8)	0.0201 (6)	−0.0032 (6)	0.0025 (5)	0.0013 (6)
C67	0.0248 (7)	0.0278 (8)	0.0275 (7)	−0.0047 (6)	0.0085 (6)	−0.0011 (6)
O67	0.0382 (6)	0.0295 (6)	0.0383 (6)	−0.0067 (5)	0.0040 (5)	0.0040 (5)
C61	0.0204 (7)	0.0315 (8)	0.0248 (7)	−0.0013 (6)	0.0065 (6)	−0.0036 (6)
C62	0.0243 (7)	0.0369 (9)	0.0306 (8)	−0.0080 (6)	0.0098 (6)	−0.0069 (7)
O62	0.0417 (7)	0.0394 (7)	0.0410 (7)	−0.0167 (5)	0.0072 (5)	−0.0067 (5)
C63	0.0282 (8)	0.0547 (11)	0.0288 (8)	−0.0130 (7)	0.0057 (6)	−0.0085 (8)
C64	0.0291 (8)	0.0612 (12)	0.0259 (8)	−0.0008 (8)	0.0017 (6)	0.0009 (8)
C65	0.0345 (9)	0.0411 (10)	0.0313 (8)	0.0041 (7)	0.0065 (7)	0.0043 (7)
C66	0.0275 (7)	0.0333 (8)	0.0272 (8)	−0.0005 (6)	0.0061 (6)	−0.0025 (6)
C7	0.0205 (7)	0.0293 (8)	0.0187 (6)	−0.0046 (5)	0.0035 (5)	0.0009 (6)
C71	0.0206 (7)	0.0372 (8)	0.0193 (7)	−0.0061 (6)	0.0039 (5)	−0.0048 (6)
C72	0.0273 (8)	0.0428 (9)	0.0260 (8)	−0.0091 (7)	0.0072 (6)	−0.0005 (7)
C73	0.0279 (8)	0.0571 (11)	0.0345 (9)	−0.0163 (8)	0.0101 (7)	−0.0012 (8)
C74	0.0194 (7)	0.0691 (13)	0.0337 (9)	−0.0083 (8)	0.0062 (6)	−0.0070 (8)
C75	0.0240 (8)	0.0532 (11)	0.0328 (9)	0.0010 (7)	0.0044 (6)	−0.0077 (8)
C76	0.0222 (7)	0.0414 (9)	0.0266 (7)	−0.0032 (6)	0.0047 (6)	−0.0052 (7)
N7A	0.0178 (6)	0.0292 (6)	0.0196 (6)	−0.0027 (5)	0.0045 (4)	−0.0018 (5)

Geometric parameters (Å, º) top

N1—C2	1.3505 (18)	C51—H51C	0.98
C2—C3	1.4013 (19)	C6—C67	1.496 (2)
C3—C3A	1.377 (2)	C67—O67	1.2418 (19)
C3A—N4	1.3525 (18)	C67—C61	1.468 (2)
N4—C5	1.3141 (18)	C61—C66	1.400 (2)
C5—C6	1.4342 (19)	C61—C62	1.413 (2)
C6—C7	1.376 (2)	C62—O62	1.346 (2)
C7—N7A	1.3675 (18)	C62—C63	1.384 (2)
N7A—N1	1.3603 (16)	O62—H62	0.96
C3A—N7A	1.4011 (17)	C63—C64	1.373 (3)
C2—C21	1.472 (2)	C63—H63	0.95
C21—C26	1.397 (2)	C64—C65	1.389 (2)
C21—C22	1.399 (2)	C64—H64	0.95
C22—C23	1.389 (2)	C65—C66	1.379 (2)
C22—H22	0.95	C65—H65	0.95
C23—C24	1.387 (2)	C66—H66	0.95
C23—H23	0.95	C7—C71	1.4857 (19)
C24—C25	1.393 (2)	C71—C76	1.393 (2)
C24—C241	1.505 (2)	C71—C72	1.395 (2)
C241—H24A	0.98	C72—C73	1.392 (2)
C241—H24B	0.98	C72—H72	0.95
C241—H24C	0.98	C73—C74	1.380 (3)
C25—C26	1.388 (2)	C73—H73	0.95
C25—H25	0.95	C74—C75	1.380 (3)
C26—H26	0.95	C74—H74	0.95
C3—H3	0.95	C75—C76	1.390 (2)
C5—C51	1.502 (2)	C75—H75	0.95
C51—H51A	0.98	C76—H76	0.95
C51—H51B	0.98

C2—N1—N7A	103.70 (11)	O67—C67—C61	120.77 (13)
N1—C2—C3	113.00 (13)	O67—C67—C6	118.40 (13)
N1—C2—C21	120.14 (12)	C61—C67—C6	120.68 (13)
C3—C2—C21	126.83 (12)	C66—C61—C62	118.34 (14)
C26—C21—C22	118.38 (14)	C66—C61—C67	122.14 (13)
C26—C21—C2	121.83 (13)	C62—C61—C67	119.42 (14)
C22—C21—C2	119.77 (13)	O62—C62—C63	117.67 (14)
C23—C22—C21	120.56 (14)	O62—C62—C61	122.05 (14)
C23—C22—H22	119.7	C63—C62—C61	120.28 (15)
C21—C22—H22	119.7	C62—O62—H62	105.2
C24—C23—C22	121.35 (14)	C64—C63—C62	119.82 (15)
C24—C23—H23	119.3	C64—C63—H63	120.1
C22—C23—H23	119.3	C62—C63—H63	120.1
C23—C24—C25	117.82 (14)	C63—C64—C65	121.32 (15)
C23—C24—C241	121.09 (14)	C63—C64—H64	119.3
C25—C24—C241	121.07 (14)	C65—C64—H64	119.3
C24—C241—H24A	109.5	C66—C65—C64	119.18 (16)
C24—C241—H24B	109.5	C66—C65—H65	120.4
H24A—C241—H24B	109.5	C64—C65—H65	120.4
C24—C241—H24C	109.5	C65—C66—C61	121.05 (15)
H24A—C241—H24C	109.5	C65—C66—H66	119.5
H24B—C241—H24C	109.5	C61—C66—H66	119.5
C26—C25—C24	121.68 (14)	N7A—C7—C6	116.24 (12)
C26—C25—H25	119.2	N7A—C7—C71	119.98 (12)
C24—C25—H25	119.2	C6—C7—C71	123.77 (13)
C25—C26—C21	120.20 (14)	C76—C71—C72	119.58 (14)
C25—C26—H26	119.9	C76—C71—C7	121.17 (13)
C21—C26—H26	119.9	C72—C71—C7	119.10 (14)
C3A—C3—C2	105.11 (12)	C73—C72—C71	119.65 (16)
C3A—C3—H3	127.4	C73—C72—H72	120.2
C2—C3—H3	127.4	C71—C72—H72	120.2
N4—C3A—C3	132.04 (13)	C74—C73—C72	120.58 (16)
N4—C3A—N7A	121.80 (12)	C74—C73—H73	119.7
C3—C3A—N7A	106.16 (12)	C72—C73—H73	119.7
C5—N4—C3A	118.00 (12)	C75—C74—C73	119.77 (15)
N4—C5—C6	121.89 (13)	C75—C74—H74	120.1
N4—C5—C51	116.77 (13)	C73—C74—H74	120.1
C6—C5—C51	121.29 (13)	C74—C75—C76	120.53 (17)
C5—C51—H51A	109.5	C74—C75—H75	119.7
C5—C51—H51B	109.5	C76—C75—H75	119.7
H51A—C51—H51B	109.5	C75—C76—C71	119.85 (15)
C5—C51—H51C	109.5	C75—C76—H76	120.1
H51A—C51—H51C	109.5	C71—C76—H76	120.1
H51B—C51—H51C	109.5	N1—N7A—C7	126.51 (11)
C7—C6—C5	120.48 (13)	N1—N7A—C3A	112.01 (11)
C7—C6—C67	121.65 (13)	C7—N7A—C3A	121.43 (12)
C5—C6—C67	117.86 (13)

N7A—N1—C2—C3	−1.32 (15)	C67—C61—C62—O62	2.6 (2)
N7A—N1—C2—C21	176.72 (12)	C66—C61—C62—C63	0.3 (2)
N1—C2—C21—C26	−2.2 (2)	C67—C61—C62—C63	−176.11 (14)
C3—C2—C21—C26	175.57 (14)	O62—C62—C63—C64	−177.97 (15)
N1—C2—C21—C22	179.38 (13)	C61—C62—C63—C64	0.8 (2)
C3—C2—C21—C22	−2.9 (2)	C62—C63—C64—C65	−0.9 (3)
C26—C21—C22—C23	0.3 (2)	C63—C64—C65—C66	−0.1 (3)
C2—C21—C22—C23	178.82 (13)	C64—C65—C66—C61	1.2 (2)
C21—C22—C23—C24	−0.2 (2)	C62—C61—C66—C65	−1.3 (2)
C22—C23—C24—C25	−0.6 (2)	C67—C61—C66—C65	174.98 (14)
C22—C23—C24—C241	177.57 (14)	C5—C6—C7—N7A	2.6 (2)
C23—C24—C25—C26	1.1 (2)	C67—C6—C7—N7A	−175.93 (12)
C241—C24—C25—C26	−176.99 (14)	C5—C6—C7—C71	−178.45 (13)
C24—C25—C26—C21	−1.0 (2)	C67—C6—C7—C71	3.0 (2)
C22—C21—C26—C25	0.2 (2)	N7A—C7—C71—C76	47.23 (19)
C2—C21—C26—C25	−178.22 (13)	C6—C7—C71—C76	−131.71 (15)
N1—C2—C3—C3A	0.66 (16)	N7A—C7—C71—C72	−137.25 (14)
C21—C2—C3—C3A	−177.23 (13)	C6—C7—C71—C72	43.8 (2)
C2—C3—C3A—N4	−179.55 (14)	C76—C71—C72—C73	2.0 (2)
C2—C3—C3A—N7A	0.29 (15)	C7—C71—C72—C73	−173.62 (14)
C3—C3A—N4—C5	−177.43 (15)	C71—C72—C73—C74	−0.3 (2)
N7A—C3A—N4—C5	2.75 (19)	C72—C73—C74—C75	−0.7 (3)
C3A—N4—C5—C6	0.7 (2)	C73—C74—C75—C76	0.1 (3)
C3A—N4—C5—C51	178.12 (12)	C74—C75—C76—C71	1.6 (2)
N4—C5—C6—C7	−3.5 (2)	C72—C71—C76—C75	−2.6 (2)
C51—C5—C6—C7	179.21 (13)	C7—C71—C76—C75	172.87 (13)
N4—C5—C6—C67	175.04 (13)	C2—N1—N7A—C7	−176.01 (13)
C51—C5—C6—C67	−2.2 (2)	C2—N1—N7A—C3A	1.50 (14)
C7—C6—C67—O67	−116.63 (16)	C6—C7—N7A—N1	178.09 (12)
C5—C6—C67—O67	64.82 (18)	C71—C7—N7A—N1	−0.9 (2)
C7—C6—C67—C61	67.74 (19)	C6—C7—N7A—C3A	0.80 (19)
C5—C6—C67—C61	−110.80 (15)	C71—C7—N7A—C3A	−178.21 (12)
O67—C67—C61—C66	−168.53 (14)	N4—C3A—N7A—N1	178.71 (12)
C6—C67—C61—C66	7.0 (2)	C3—C3A—N7A—N1	−1.15 (15)
O67—C67—C61—C62	7.7 (2)	N4—C3A—N7A—C7	−3.6 (2)
C6—C67—C61—C62	−176.77 (13)	C3—C3A—N7A—C7	176.50 (12)
C66—C61—C62—O62	178.99 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O62—H62···O67	0.96	1.68	2.554 (2)	150
C3—H3···N4ⁱ	0.95	2.61	3.543 (2)	168
C22—H22···N4ⁱ	0.95	2.57	3.513 (2)	174
C74—H74···O62ⁱⁱ	0.95	2.55	3.422 (2)	154
C76—H76···O67ⁱⁱⁱ	0.95	2.56	3.444 (2)	155

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

Acknowledgements

X-ray data were collected at the EPSRC X-ray Crystallographic Service, University of Southampton, UK. JC and JT thank the Consejería de Innovación, Ciencia y Empresa (Junta de Andalucía, Spain) and the Universidad de Jaén for financial support. JT also thanks the Universidad de Jaén for a research scholarship supporting a short stay at the EPSRC X-ray Crystallographic Service, University of Southampton, UK. JP thanks COLCIENCIAS, UNIVALLE (Universidad del Valle, Colombia), for financial support.

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