8-tert-Butyl-7,10-diphenyl-6,10-dihydro-5H-benzo[h]pyrazolo[3,4-b]quinoline

Low, J.N.; Cobo, J.; Portilla, J.; Quiroga, J.; Glidewell, C.

doi:10.1107/S1600536807017631

8-tert-Butyl-7,10-diphenyl-6,10-dihydro-5H-benzo[h]pyrazolo[3,4-b]quinoline

J. N. Low, J. Cobo, J. Portilla, J. Quiroga and C. Glidewell

In the title compound, C₃₀H₂₇N₃, the non-aromatic carbocyclic ring adopts an almost perfect screw-boat conformation; the molecules are linked into cyclic centrosymmetric dimers by pairs of C—H

π(pyridyl) hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807017631/lh2364sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807017631/lh2364Isup2.hkl Contains datablock I

CCDC reference: 647695

checkCIF report

Key indicators

Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.004 Å
R factor = 0.071
wR factor = 0.238
Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C81

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
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Comment top

Pyrazolo[3,4-b]quinolines are of interest as possible antiviral and antimalarial agents, and because of their other biological properties, such as parasiticidic, bactericidal, vasodilator, and enzyme-inhibitory activity (Quiroga et al., 2001). Here we report the structure of the title compound (I) (Fig. 2) as a new example of this class of compound.

Within the molecule of (I), the bond distances show strong bond fixation within the pyrazolo ring, and electronic delocalization in the aryl and pyridyl rings (Table 1). For the C4A/C5/C6/C6A/C11A/C11B the ring-puckering parameters (Cremer & Pople, 1975) are θ = 116.6 (5)° and φ = 269.7 (5)°, very close to the ideal values, θ = 112.5° and φ = (60k + 30)° (k = integer) for an idealized screw-boat conformation (Evans & Boeyens, 1989).

In the crystal structure, molecules of (I) are linked by paired C—H..π(pyridyl) hydrogen bonds (Table 2) to form cyclic centrosymmetric dimers, but there are no direction-specific interactions between adjacent dimers.

In the 8-methyl analogue (II) (Portilla et al., 2005) the molecules are linked into sheets by a combination of C—H···π(arene) and C—H···π(pyridyl) hydrogen bonds, while in (III) (Abonia et al., 2005), the molecules are linked into chains of rings by a combination of C—H···O and C—H···π(arene) hydrogen bonds.

Related literature top

For related literature, see: Cremer & Pople (1975); Evans & Boeyens (1989); Quiroga et al. (2001).

Experimental top

A mixture of 5-amino-3-tert-butyl-1-phenylpyrazole (1 mmol) and 2-benzylidene-1-tetralone (1 mmol) was thoroughly mixed at room temperature. The mixture was heated in an oil-bath at 423 K for 3.5 min. It was then cooled to ambient temperature and permitted to solidify. The resulting solid was extracted with ethanol; the solvent was removed from the extract under reduced pressure and the product was recrystallized from ethanol/dimethylformamide (X:Y, v/v), to afford yellow crystals of the title compound (I) which were suitable for single-crystal X-ray diffraction. Yield 70%, m. p. 499–451 K;. MS (70 eV) m/z (%) 429 (56, M⁺), 414 (100), 387 (16), 77 (20), 41 (18).

Structure description top

For related literature, see: Cremer & Pople (1975); Evans & Boeyens (1989); Quiroga et al. (2001).

Computing details top

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) and WinGX (Farrugia, 1999); 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).

Figures top

	Fig. 1. Compounds (I), (II) and (III).
	Fig. 2. The molecular structure of compound (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 3. Part of the crystal structure of compound (I) showing the formation of a centrosymmetric hydrogen-bonded dimer.. For the sake of clarity the H atoms not involved in the motif shown have been omitted. The atoms marked with an asterisk (*) are at the symmetry position (1 - x, 1 - y, 1 - z).

8-tert-Butyl-7,10-diphenyl-6,10-dihydro-5H-benzo[h]pyrazolo[3,4-b]quinoline top

Crystal data top

C₃₀H₂₇N₃	Z = 2
M_r = 429.55	F(000) = 456
Triclinic, P1	D_x = 1.254 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.516 (2) Å	Cell parameters from 5226 reflections
b = 10.406 (3) Å	θ = 3.1–27.5°
c = 11.868 (5) Å	µ = 0.07 mm⁻¹
α = 99.52 (4)°	T = 120 K
β = 100.42 (2)°	Plate, colourless
γ = 91.55 (4)°	0.41 × 0.23 × 0.11 mm
V = 1137.9 (7) Å³

Data collection top

Bruker-Nonius KappaCCD diffractometer	5226 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode	2735 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −13→13
T_min = 0.977, T_max = 0.992	l = −15→15
28777 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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.238	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.1424P)²] where P = (F_o² + 2F_c²)/3
5226 reflections	(Δ/σ)_max < 0.001
301 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₃₀H₂₇N₃	γ = 91.55 (4)°
M_r = 429.55	V = 1137.9 (7) Å³
Triclinic, P1	Z = 2
a = 9.516 (2) Å	Mo Kα radiation
b = 10.406 (3) Å	µ = 0.07 mm⁻¹
c = 11.868 (5) Å	T = 120 K
α = 99.52 (4)°	0.41 × 0.23 × 0.11 mm
β = 100.42 (2)°

Data collection top

Bruker-Nonius KappaCCD diffractometer	5226 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2735 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.992	R_int = 0.061
28777 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.071	0 restraints
wR(F²) = 0.238	H-atom parameters constrained
S = 1.03	Δρ_max = 0.37 e Å⁻³
5226 reflections	Δρ_min = −0.31 e Å⁻³
301 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.1837 (3)	0.3064 (3)	0.1069 (2)	0.0396 (6)
C2	0.0673 (3)	0.3333 (3)	0.0288 (2)	0.0444 (7)
C3	−0.0594 (3)	0.3643 (3)	0.0658 (2)	0.0425 (7)
C4	−0.0684 (3)	0.3690 (3)	0.1804 (2)	0.0423 (7)
C4A	0.0477 (3)	0.3419 (2)	0.2610 (2)	0.0362 (6)
C5	0.0376 (3)	0.3404 (3)	0.3840 (2)	0.0501 (7)
C6	0.1720 (3)	0.3745 (3)	0.4663 (2)	0.0466 (7)
C6A	0.2988 (3)	0.3109 (2)	0.42886 (19)	0.0328 (6)
C7	0.4173 (3)	0.2866 (2)	0.50956 (19)	0.0319 (6)
C71	0.4101 (3)	0.3216 (2)	0.6355 (2)	0.0336 (6)
C72	0.4450 (3)	0.4504 (2)	0.6922 (2)	0.0393 (6)
C73	0.4334 (3)	0.4871 (3)	0.8068 (2)	0.0426 (7)
C74	0.3865 (3)	0.3981 (3)	0.8668 (2)	0.0433 (7)
C75	0.3494 (3)	0.2704 (3)	0.8119 (2)	0.0464 (7)
C76	0.3612 (3)	0.2329 (3)	0.6964 (2)	0.0387 (6)
C7A	0.5359 (3)	0.2327 (2)	0.46623 (19)	0.0321 (6)
C8	0.6766 (3)	0.1911 (2)	0.5083 (2)	0.0336 (6)
C81	0.7608 (3)	0.1828 (3)	0.6284 (2)	0.0372 (6)
C82	0.6882 (3)	0.0770 (3)	0.6768 (2)	0.0585 (8)
C83	0.7713 (4)	0.3126 (3)	0.7121 (3)	0.0682 (10)
C84	0.9126 (3)	0.1438 (4)	0.6198 (2)	0.0644 (9)
N9	0.7386 (2)	0.1471 (2)	0.41949 (16)	0.0354 (5)
N10	0.6469 (2)	0.15871 (19)	0.31858 (16)	0.0326 (5)
C101	0.6912 (3)	0.1158 (2)	0.21105 (19)	0.0323 (6)
C102	0.6118 (3)	0.1379 (2)	0.1067 (2)	0.0377 (6)
C103	0.6587 (3)	0.0932 (3)	0.0044 (2)	0.0416 (7)
C104	0.7829 (3)	0.0277 (3)	0.0042 (2)	0.0411 (7)
C105	0.8610 (3)	0.0077 (3)	0.1081 (2)	0.0422 (7)
C106	0.8164 (3)	0.0519 (2)	0.2120 (2)	0.0379 (6)
C10A	0.5221 (3)	0.2093 (2)	0.34415 (19)	0.0307 (6)
N11	0.4113 (2)	0.23114 (18)	0.26481 (15)	0.0312 (5)
C11A	0.2992 (3)	0.2826 (2)	0.30822 (19)	0.0310 (6)
C11B	0.1760 (2)	0.3099 (2)	0.22402 (19)	0.0319 (6)
H1	0.2704	0.2851	0.0809	0.048*
H2	0.0739	0.3305	−0.0504	0.053*
H3	−0.1399	0.3824	0.0119	0.051*
H4	−0.1555	0.3912	0.2052	0.051*
H5A	−0.0339	0.4024	0.4060	0.060*
H5B	0.0020	0.2522	0.3905	0.060*
H6A	0.1611	0.3500	0.5415	0.056*
H6B	0.1908	0.4703	0.4794	0.056*
H72	0.4770	0.5131	0.6512	0.047*
H73	0.4582	0.5747	0.8446	0.051*
H74	0.3792	0.4239	0.9461	0.052*
H75	0.3161	0.2087	0.8532	0.056*
H76	0.3354	0.1454	0.6588	0.046*
H82A	0.6853	−0.0068	0.6243	0.088*
H82B	0.5905	0.0999	0.6833	0.088*
H82C	0.7424	0.0699	0.7538	0.088*
H83A	0.6752	0.3366	0.7230	0.102*
H83B	0.8161	0.3805	0.6798	0.102*
H83C	0.8294	0.3039	0.7873	0.102*
H84A	0.9598	0.2081	0.5851	0.097*
H84B	0.9085	0.0576	0.5709	0.097*
H84C	0.9667	0.1407	0.6977	0.097*
H102	0.5263	0.1830	0.1055	0.045*
H103	0.6044	0.1080	−0.0673	0.050*
H104	0.8136	−0.0031	−0.0667	0.049*
H105	0.9469	−0.0370	0.1090	0.051*
H106	0.8719	0.0381	0.2836	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0371 (15)	0.0450 (16)	0.0377 (14)	0.0060 (12)	0.0073 (12)	0.0092 (12)
C2	0.0479 (17)	0.0513 (17)	0.0344 (14)	0.0098 (13)	0.0033 (12)	0.0124 (12)
C3	0.0366 (15)	0.0459 (16)	0.0439 (16)	0.0065 (12)	0.0009 (12)	0.0108 (13)
C4	0.0361 (15)	0.0430 (16)	0.0454 (16)	0.0021 (12)	0.0047 (12)	0.0039 (12)
C4A	0.0343 (14)	0.0382 (14)	0.0368 (14)	0.0020 (11)	0.0079 (11)	0.0068 (11)
C5	0.0390 (16)	0.071 (2)	0.0409 (15)	0.0066 (14)	0.0102 (13)	0.0071 (14)
C6	0.0419 (16)	0.0659 (19)	0.0328 (14)	0.0127 (14)	0.0093 (12)	0.0067 (13)
C6A	0.0341 (14)	0.0350 (14)	0.0308 (13)	0.0050 (11)	0.0103 (11)	0.0055 (10)
C7	0.0343 (14)	0.0318 (13)	0.0306 (13)	−0.0006 (11)	0.0094 (11)	0.0047 (10)
C71	0.0318 (14)	0.0402 (15)	0.0293 (13)	0.0036 (11)	0.0056 (10)	0.0069 (11)
C72	0.0428 (16)	0.0407 (15)	0.0343 (14)	−0.0009 (12)	0.0074 (12)	0.0067 (12)
C73	0.0457 (16)	0.0451 (16)	0.0334 (14)	−0.0008 (13)	0.0040 (12)	0.0005 (12)
C74	0.0433 (16)	0.0543 (18)	0.0307 (13)	0.0014 (13)	0.0064 (12)	0.0035 (13)
C75	0.0506 (17)	0.0535 (18)	0.0381 (15)	−0.0047 (14)	0.0134 (13)	0.0121 (13)
C76	0.0432 (15)	0.0385 (15)	0.0352 (14)	−0.0029 (12)	0.0120 (12)	0.0044 (11)
C7A	0.0356 (14)	0.0352 (14)	0.0272 (12)	0.0023 (11)	0.0085 (10)	0.0078 (10)
C8	0.0327 (13)	0.0355 (14)	0.0336 (13)	0.0014 (11)	0.0051 (11)	0.0106 (11)
C81	0.0362 (14)	0.0455 (15)	0.0311 (13)	0.0060 (12)	0.0044 (11)	0.0122 (11)
C82	0.065 (2)	0.072 (2)	0.0438 (17)	0.0035 (17)	0.0081 (15)	0.0286 (15)
C83	0.074 (2)	0.0517 (19)	0.0589 (19)	0.0055 (16)	−0.0272 (17)	−0.0052 (15)
C84	0.0457 (18)	0.110 (3)	0.0404 (16)	0.0251 (18)	0.0025 (14)	0.0251 (17)
N9	0.0345 (12)	0.0423 (12)	0.0298 (11)	0.0028 (9)	0.0043 (9)	0.0091 (9)
N10	0.0298 (11)	0.0410 (12)	0.0280 (11)	0.0047 (9)	0.0062 (9)	0.0072 (9)
C101	0.0318 (14)	0.0367 (14)	0.0291 (13)	0.0002 (11)	0.0089 (10)	0.0042 (10)
C102	0.0341 (14)	0.0458 (15)	0.0323 (13)	0.0034 (12)	0.0057 (11)	0.0048 (11)
C103	0.0419 (16)	0.0562 (17)	0.0272 (13)	0.0009 (13)	0.0071 (11)	0.0081 (12)
C104	0.0418 (16)	0.0478 (16)	0.0353 (14)	0.0024 (13)	0.0137 (12)	0.0048 (12)
C105	0.0402 (15)	0.0475 (16)	0.0436 (15)	0.0100 (12)	0.0178 (13)	0.0097 (12)
C106	0.0363 (15)	0.0447 (16)	0.0346 (13)	0.0072 (12)	0.0069 (11)	0.0111 (11)
C10A	0.0317 (13)	0.0287 (13)	0.0315 (13)	0.0003 (10)	0.0062 (11)	0.0051 (10)
N11	0.0308 (11)	0.0341 (11)	0.0289 (10)	0.0041 (9)	0.0052 (9)	0.0061 (9)
C11A	0.0330 (14)	0.0299 (13)	0.0312 (13)	−0.0008 (11)	0.0085 (11)	0.0058 (10)
C11B	0.0313 (14)	0.0332 (13)	0.0300 (13)	0.0003 (11)	0.0016 (10)	0.0069 (10)

Geometric parameters (Å, º) top

C1—C2	1.376 (4)	C8—C81	1.521 (3)
C1—C11B	1.400 (3)	C81—C82	1.526 (4)
C1—H1	0.95	C81—C84	1.527 (4)
C2—C3	1.384 (4)	C81—C83	1.528 (4)
C2—H2	0.95	C82—H82A	0.98
C3—C4	1.370 (4)	C82—H82B	0.98
C3—H3	0.95	C82—H82C	0.98
C4—C4A	1.393 (4)	C83—H83A	0.98
C4—H4	0.95	C83—H83B	0.98
C4A—C11B	1.401 (3)	C83—H83C	0.98
C4A—C5	1.482 (4)	C84—H84A	0.98
C5—C6	1.458 (4)	C84—H84B	0.98
C5—H5A	0.99	C84—H84C	0.98
C5—H5B	0.99	N9—N10	1.373 (3)
C6—C6A	1.494 (3)	N10—C10A	1.376 (3)
C6—H6A	0.99	N10—C101	1.422 (3)
C6—H6B	0.99	C101—C106	1.380 (3)
C6A—C7	1.399 (3)	C101—C102	1.386 (3)
C7—C7A	1.415 (3)	C102—C103	1.382 (3)
C7—C71	1.493 (3)	C102—H102	0.95
C71—C76	1.382 (3)	C103—C104	1.381 (4)
C71—C72	1.399 (3)	C103—H103	0.95
C72—C73	1.377 (3)	C104—C105	1.370 (4)
C72—H72	0.95	C104—H104	0.95
C73—C74	1.369 (4)	C105—C106	1.388 (3)
C73—H73	0.95	C105—H105	0.95
C74—C75	1.386 (4)	C106—H106	0.95
C74—H74	0.95	C10A—N11	1.332 (3)
C75—C76	1.387 (3)	N11—C11A	1.352 (3)
C75—H75	0.95	C11A—C6A	1.414 (3)
C76—H76	0.95	C7A—C10A	1.410 (3)
C7A—C8	1.446 (3)	C11A—C11B	1.464 (3)
C8—N9	1.322 (3)

C2—C1—C11B	120.8 (2)	C8—C81—C82	108.7 (2)
C2—C1—H1	119.6	C8—C81—C84	110.0 (2)
C11B—C1—H1	119.6	C82—C81—C84	107.9 (2)
C1—C2—C3	120.0 (2)	C8—C81—C83	112.2 (2)
C1—C2—H2	120.0	C82—C81—C83	109.8 (2)
C3—C2—H2	120.0	C84—C81—C83	108.1 (2)
C4—C3—C2	119.9 (2)	C81—C82—H82A	109.5
C4—C3—H3	120.0	C81—C82—H82B	109.5
C2—C3—H3	120.0	H82A—C82—H82B	109.5
C3—C4—C4A	121.2 (2)	C81—C82—H82C	109.5
C3—C4—H4	119.4	H82A—C82—H82C	109.5
C4A—C4—H4	119.4	H82B—C82—H82C	109.5
C4—C4A—C11B	119.2 (2)	C81—C83—H83A	109.5
C4—C4A—C5	121.8 (2)	C81—C83—H83B	109.5
C11B—C4A—C5	119.0 (2)	H83A—C83—H83B	109.5
C6—C5—C4A	114.5 (2)	C81—C83—H83C	109.5
C6—C5—H5A	108.6	H83A—C83—H83C	109.5
C4A—C5—H5A	108.6	H83B—C83—H83C	109.5
C6—C5—H5B	108.6	C81—C84—H84A	109.5
C4A—C5—H5B	108.6	C81—C84—H84B	109.5
H5A—C5—H5B	107.6	H84A—C84—H84B	109.5
C5—C6—C6A	114.7 (2)	C81—C84—H84C	109.5
C5—C6—H6A	108.6	H84A—C84—H84C	109.5
C6A—C6—H6A	108.6	H84B—C84—H84C	109.5
C5—C6—H6B	108.6	C8—N9—N10	108.3 (2)
C6A—C6—H6B	108.6	N9—N10—C10A	109.87 (18)
H6A—C6—H6B	107.6	N9—N10—C101	118.18 (19)
C7—C6A—C11A	120.5 (2)	C10A—N10—C101	131.9 (2)
C7—C6A—C6	121.7 (2)	C106—C101—C102	120.0 (2)
C11A—C6A—C6	117.7 (2)	C106—C101—N10	118.6 (2)
C6A—C7—C7A	117.8 (2)	C102—C101—N10	121.3 (2)
C6A—C7—C71	117.4 (2)	C103—C102—C101	119.1 (2)
C7A—C7—C71	124.7 (2)	C103—C102—H102	120.4
C76—C71—C72	118.6 (2)	C101—C102—H102	120.4
C76—C71—C7	122.2 (2)	C104—C103—C102	121.3 (2)
C72—C71—C7	119.1 (2)	C104—C103—H103	119.3
C73—C72—C71	120.5 (2)	C102—C103—H103	119.3
C73—C72—H72	119.7	C105—C104—C103	118.9 (2)
C71—C72—H72	119.7	C105—C104—H104	120.5
C74—C73—C72	120.4 (3)	C103—C104—H104	120.5
C74—C73—H73	119.8	C104—C105—C106	120.8 (2)
C72—C73—H73	119.8	C104—C105—H105	119.6
C73—C74—C75	120.0 (2)	C106—C105—H105	119.6
C73—C74—H74	120.0	C101—C106—C105	119.7 (2)
C75—C74—H74	120.0	C101—C106—H106	120.1
C74—C75—C76	119.8 (2)	C105—C106—H106	120.1
C74—C75—H75	120.1	N11—C10A—N10	124.4 (2)
C76—C75—H75	120.1	N11—C10A—C7A	128.1 (2)
C71—C76—C75	120.7 (2)	N10—C10A—C7A	107.5 (2)
C71—C76—H76	119.7	C10A—N11—C11A	115.07 (19)
C75—C76—H76	119.7	N11—C11A—C6A	122.7 (2)
C10A—C7A—C7	115.7 (2)	N11—C11A—C11B	116.8 (2)
C10A—C7A—C8	104.4 (2)	C6A—C11A—C11B	120.4 (2)
C7—C7A—C8	139.8 (2)	C1—C11B—C4A	118.9 (2)
N9—C8—C7A	109.9 (2)	C1—C11B—C11A	121.4 (2)
N9—C8—C81	116.1 (2)	C4A—C11B—C11A	119.6 (2)
C7A—C8—C81	133.9 (2)

C11B—C1—C2—C3	0.0 (4)	C81—C8—N9—N10	178.42 (19)
C1—C2—C3—C4	0.4 (4)	C8—N9—N10—C10A	−1.2 (3)
C2—C3—C4—C4A	−0.6 (4)	C8—N9—N10—C101	−179.43 (19)
C3—C4—C4A—C11B	0.3 (4)	N9—N10—C101—C106	6.9 (3)
C3—C4—C4A—C5	−177.1 (2)	C10A—N10—C101—C106	−170.9 (2)
C4—C4A—C5—C6	−151.3 (3)	N9—N10—C101—C102	−172.6 (2)
C11B—C4A—C5—C6	31.3 (4)	C10A—N10—C101—C102	9.5 (4)
C4A—C5—C6—C6A	−44.5 (4)	C106—C101—C102—C103	1.0 (4)
C5—C6—C6A—C7	−152.8 (2)	N10—C101—C102—C103	−179.4 (2)
C5—C6—C6A—C11A	30.8 (4)	C101—C102—C103—C104	−0.2 (4)
C11A—C6A—C7—C7A	−0.3 (3)	C102—C103—C104—C105	−0.4 (4)
C6—C6A—C7—C7A	−176.6 (2)	C103—C104—C105—C106	0.3 (4)
C11A—C6A—C7—C71	178.8 (2)	C102—C101—C106—C105	−1.2 (4)
C6—C6A—C7—C71	2.5 (4)	N10—C101—C106—C105	179.2 (2)
C6A—C7—C71—C76	92.4 (3)	C104—C105—C106—C101	0.5 (4)
C7A—C7—C71—C76	−88.6 (3)	N9—N10—C10A—N11	−179.3 (2)
C6A—C7—C71—C72	−83.3 (3)	C101—N10—C10A—N11	−1.4 (4)
C7A—C7—C71—C72	95.7 (3)	N9—N10—C10A—C7A	0.9 (3)
C76—C71—C72—C73	1.3 (4)	C101—N10—C10A—C7A	178.9 (2)
C7—C71—C72—C73	177.1 (2)	C7—C7A—C10A—N11	−0.3 (4)
C71—C72—C73—C74	−0.5 (4)	C8—C7A—C10A—N11	179.9 (2)
C72—C73—C74—C75	−0.4 (4)	C7—C7A—C10A—N10	179.4 (2)
C73—C74—C75—C76	0.5 (4)	C8—C7A—C10A—N10	−0.4 (2)
C72—C71—C76—C75	−1.1 (4)	N10—C10A—N11—C11A	−179.4 (2)
C7—C71—C76—C75	−176.9 (2)	C7A—C10A—N11—C11A	0.3 (3)
C74—C75—C76—C71	0.3 (4)	C10A—N11—C11A—C6A	−0.3 (3)
C6A—C7—C7A—C10A	0.3 (3)	C10A—N11—C11A—C11B	179.1 (2)
C71—C7—C7A—C10A	−178.7 (2)	C7—C6A—C11A—N11	0.3 (4)
C6A—C7—C7A—C8	179.9 (3)	C6—C6A—C11A—N11	176.7 (2)
C71—C7—C7A—C8	0.9 (5)	C7—C6A—C11A—C11B	−179.1 (2)
C10A—C7A—C8—N9	−0.3 (3)	C6—C6A—C11A—C11B	−2.7 (3)
C7—C7A—C8—N9	−180.0 (3)	C2—C1—C11B—C4A	−0.3 (4)
C10A—C7A—C8—C81	−177.2 (3)	C2—C1—C11B—C11A	−179.5 (2)
C7—C7A—C8—C81	3.1 (5)	C4—C4A—C11B—C1	0.1 (4)
N9—C8—C81—C82	−108.9 (3)	C5—C4A—C11B—C1	177.6 (2)
C7A—C8—C81—C82	67.9 (3)	C4—C4A—C11B—C11A	179.3 (2)
N9—C8—C81—C84	9.1 (3)	C5—C4A—C11B—C11A	−3.2 (4)
C7A—C8—C81—C84	−174.1 (3)	N11—C11A—C11B—C1	−11.7 (3)
N9—C8—C81—C83	129.5 (3)	C6A—C11A—C11B—C1	167.7 (2)
C7A—C8—C81—C83	−53.8 (4)	N11—C11A—C11B—C4A	169.1 (2)
C7A—C8—N9—N10	0.9 (3)	C6A—C11A—C11B—C4A	−11.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C72—H72···Cgⁱ	0.95	2.70	3.607 (3)	159

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₃₀H₂₇N₃
M_r	429.55
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	9.516 (2), 10.406 (3), 11.868 (5)
α, β, γ (°)	99.52 (4), 100.42 (2), 91.55 (4)
V (Å³)	1137.9 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.41 × 0.23 × 0.11

Data collection
Diffractometer	Bruker-Nonius KappaCCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.977, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	28777, 5226, 2735
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.071, 0.238, 1.03
No. of reflections	5226
No. of parameters	301
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.31

Computer programs: COLLECT (Hooft, 1999), DIRAX/LSQ (Duisenberg et al., 2000), EVALCCD (Duisenberg et al., 2003), SIR2004 (Burla et al., 2005) and WinGX (Farrugia, 1999), OSCAIL (McArdle, 2003) and SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 and PRPKAPPA (Ferguson, 1999).

Selected bond lengths (Å) top

C6A—C7	1.399 (3)	N10—C10A	1.376 (3)
C7—C7A	1.415 (3)	C10A—N11	1.332 (3)
C7A—C8	1.446 (3)	N11—C11A	1.352 (3)
C8—N9	1.322 (3)	C11A—C6A	1.414 (3)
N9—N10	1.373 (3)	C7A—C10A	1.410 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C72—H72···Cgⁱ	0.95	2.70	3.607 (3)	159

Symmetry code: (i) −x+1, −y+1, −z+1.

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