11-(4-Bromo­phenyl)-10-methyl-8-phenyl-6,8-di­hydro-5H-benzo­[f]­pyrazolo­[3,4-b]­quinoline

Serrano, H.; Quiroga, J.; Cobo, J.; Low, J.N.; Glidewell, C.

doi:10.1107/S1600536805014479

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 61| Part 6| June 2005| Pages o1702-o1703

https://doi.org/10.1107/S1600536805014479

11-(4-Bromophenyl)-10-methyl-8-phenyl-6,8-dihydro-5H-benzo[f]pyrazolo[3,4-b]quinoline

Hugo Serrano,^a Jairo Quiroga,^a 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, Fife KY16 9ST, Scotland
^*Correspondence e-mail: cg@st-andrews.ac.uk

(Received 4 May 2005; accepted 6 May 2005; online 14 May 2005)

The title compound, C₂₇H₂₀BrN₃, is isostructural with the chloro analogue: the molecules are linked by two independent C—H⋯π(arene) hydrogen bonds into chains of edge-fused rings.

Comment

The title compound, (I) (Fig. 1), is isostructural with 11-(4-chlorophenyl)-10-methyl-8-phenyl-6,8-dihydro-5H-benzo[f]pyrazolo[3,4-b]quinoline, (II) (Serrano et al., 2005 ).

The bond lengths and angles, and the molecular conformation, for (I) are all virtually identical with those for (II). Two independent C—H⋯π(arene) hydrogen bonds (Table 1) link the molecules of (I) into a [101] chain of centrosymmetric edge-fused rings, just as in (II). There are no direction-specific interactions between adjacent chains: C—H⋯N and C—H⋯Br hydrogen bonds, and aromatic π–π stacking interactions are all absent from the structure of (I).

Figure 1
The molecule of compound (I

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

Experimental

Equimolar amounts of 5-amino-3-methyl-1-phenylpyrazole (173 mg, 1.0 mmol), 2-tetralone (146 mg, 1.0 mmol) and 4-bromobenzaldehyde (185.0 mg, 1.0 mmol) were placed in open Pyrex-glass vessels and irradiated in a domestic microwave oven for 4 min at 600 W. The reaction mixture was then extracted with ethanol, and, after removal of the solvent, the product was recrystallized from ethanol/dimethylformamide to give crystals suitable for single-crystal X-ray diffraction.

Crystal data

C₂₇H₂₀BrN₃
M_r = 466.37
Triclinic, $[P\overline 1]$
a = 7.0237 (3) Å
b = 12.8964 (7) Å
c = 13.3517 (7) Å
α = 106.630 (3)°
β = 101.423 (3)°
γ = 102.274 (3)°
V = 1088.18 (10) Å³
Z = 2
D_x = 1.423 Mg m⁻³
Mo Kα radiation
Cell parameters from 5001 reflections
θ = 3.1–27.7°
μ = 1.91 mm⁻¹
T = 120 (2) K
Plate, colourless
0.36 × 0.14 × 0.03 mm

Data collection

Bruker–Nonius KappaCCD diffractometer
φ and ω scans
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.547, T_max = 0.945
223424 measured reflections
5001 independent reflections
3175 reflections with I > 2σ(I)
R_int = 0.085
θ_max = 27.7°
h = −8 → 9
k = −16 → 16
l = −17 → 17

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.102
S = 1.03
5001 reflections
281 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0461P)²] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bonding geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C113—H113⋯Cg1ⁱ	0.95	2.71	3.588 (3)	154
C115—H115⋯Cg2ⁱⁱ	0.95	2.81	3.589 (3)	140
Symmetry codes: (i) -x,1-y,-z; (ii) 1-x,1-y,1-z. Note: Cg1 is the centroid of ring C81–C86, and Cg2 is the centroid of ring C1,C2,C3,C4,C4A,C11B

All H atoms were located in difference maps in fully ordered sites; they were then treated as riding atoms, with C—H distances 0.95 (aromatic), 0.98 (methyl) or 0.99 Å (CH₂), and with U_iso(H) = 1.2U_eq(C), or 1.5U_eq(C) for the methyl group.

Data collection: COLLECT (Hooft, 1999 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; 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/S1600536805014479/lh6424sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536805014479/lh6424Isup2.hkl

Computing details top

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

11-(4-bromophenyl)-10-methyl-8-phenyl-6,8-dihydro-5H- benzo[f]pyrazolo[3,4-b]quinoline top

Crystal data top

C₂₇H₂₀BrN₃	Z = 2
M_r = 466.37	F(000) = 476
Triclinic, P1	D_x = 1.423 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0237 (3) Å	Cell parameters from 5001 reflections
b = 12.8964 (7) Å	θ = 3.1–27.7°
c = 13.3517 (7) Å	µ = 1.91 mm⁻¹
α = 106.630 (3)°	T = 120 K
β = 101.423 (3)°	Plate, colourless
γ = 102.274 (3)°	0.36 × 0.14 × 0.03 mm
V = 1088.18 (10) Å³

Data collection top

Bruker-Nonius 95mm CCD camera on κ goniostat diffractometer	5001 independent reflections
Radiation source: Bruker-Nonius FR91 rotating anode	3175 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.085
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.7°, θ_min = 3.1°
φ and ω scans	h = −8→9
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −16→16
T_min = 0.547, T_max = 0.945	l = −17→17
223424 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0461P)²] where P = (F_o² + 2F_c²)/3
5001 reflections	(Δ/σ)_max < 0.001
281 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

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

	x	y	z	U_iso*/U_eq
Br14	0.41479 (5)	0.13431 (3)	0.25854 (3)	0.03966 (13)
N7	0.2796 (3)	0.81718 (19)	0.26822 (18)	0.0255 (5)
N8	−0.0557 (3)	0.7067 (2)	0.15048 (19)	0.0270 (6)
N9	−0.1652 (3)	0.5942 (2)	0.10704 (19)	0.0285 (6)
C1	0.7765 (4)	0.6159 (2)	0.3633 (2)	0.0271 (7)
C2	0.9607 (4)	0.6214 (3)	0.4281 (3)	0.0330 (7)
C3	1.0668 (4)	0.7171 (3)	0.5171 (3)	0.0397 (8)
C4	0.9893 (4)	0.8088 (3)	0.5380 (2)	0.0355 (7)
C4A	0.8045 (4)	0.8053 (2)	0.4736 (2)	0.0277 (7)
C5	0.7231 (4)	0.9057 (2)	0.4936 (2)	0.0316 (7)
C6	0.6183 (4)	0.9125 (2)	0.3856 (2)	0.0285 (7)
C6A	0.4510 (4)	0.8058 (2)	0.3224 (2)	0.0244 (6)
C7A	0.1361 (4)	0.7190 (2)	0.2108 (2)	0.0252 (6)
C10	−0.0459 (4)	0.5364 (2)	0.1383 (2)	0.0252 (6)
C10A	0.1496 (4)	0.6113 (2)	0.2045 (2)	0.0224 (6)
C11	0.3307 (4)	0.6008 (2)	0.2637 (2)	0.0209 (6)
C11A	0.4864 (4)	0.7007 (2)	0.3226 (2)	0.0212 (6)
C11B	0.6911 (4)	0.7059 (2)	0.3862 (2)	0.0230 (6)
C81	−0.1493 (4)	0.7901 (2)	0.1331 (2)	0.0289 (7)
C82	−0.3588 (4)	0.7661 (3)	0.1102 (2)	0.0336 (7)
C83	−0.4501 (5)	0.8470 (3)	0.0925 (2)	0.0404 (8)
C84	−0.3341 (5)	0.9503 (3)	0.0971 (3)	0.0460 (9)
C85	−0.1276 (5)	0.9730 (3)	0.1203 (3)	0.0523 (10)
C86	−0.0334 (5)	0.8924 (3)	0.1375 (3)	0.0455 (9)
C101	−0.1264 (4)	0.4110 (2)	0.1040 (2)	0.0318 (7)
C111	0.3419 (4)	0.4862 (2)	0.2618 (2)	0.0218 (6)
C112	0.3481 (4)	0.4073 (2)	0.1668 (2)	0.0252 (6)
C113	0.3656 (4)	0.3019 (2)	0.1659 (2)	0.0268 (6)
C114	0.3778 (4)	0.2760 (2)	0.2600 (2)	0.0255 (6)
C115	0.3655 (4)	0.3515 (2)	0.3539 (2)	0.0253 (6)
C116	0.3482 (4)	0.4563 (2)	0.3542 (2)	0.0229 (6)
H1	0.7063	0.5497	0.3020	0.033*
H2	1.0147	0.5590	0.4113	0.040*
H3	1.1910	0.7200	0.5632	0.048*
H4	1.0640	0.8756	0.5977	0.043*
H5A	0.8356	0.9756	0.5350	0.038*
H5B	0.6255	0.8988	0.5373	0.038*
H6A	0.5621	0.9778	0.3986	0.034*
H6B	0.7175	0.9234	0.3435	0.034*
H10A	−0.1058	0.3878	0.1682	0.048*
H10B	−0.0546	0.3752	0.0544	0.048*
H10C	−0.2715	0.3875	0.0667	0.048*
H82	−0.4386	0.6951	0.1067	0.040*
H83	−0.5933	0.8314	0.0771	0.048*
H84	−0.3974	1.0052	0.0842	0.055*
H85	−0.0478	1.0444	0.1248	0.063*
H86	0.1097	0.9080	0.1522	0.055*
H112	0.3403	0.4258	0.1024	0.030*
H113	0.3692	0.2481	0.1012	0.032*
H115	0.3690	0.3316	0.4174	0.030*
H116	0.3405	0.5088	0.4187	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br14	0.0560 (2)	0.02559 (19)	0.0352 (2)	0.01541 (15)	0.00394 (15)	0.01040 (14)
N7	0.0255 (13)	0.0257 (14)	0.0253 (13)	0.0099 (11)	0.0047 (11)	0.0084 (11)
N8	0.0226 (12)	0.0298 (14)	0.0298 (14)	0.0122 (11)	0.0019 (11)	0.0118 (12)
N9	0.0244 (13)	0.0304 (15)	0.0294 (14)	0.0081 (11)	0.0047 (11)	0.0099 (12)
C1	0.0244 (15)	0.0284 (17)	0.0296 (17)	0.0081 (13)	0.0084 (13)	0.0104 (14)
C2	0.0241 (16)	0.0384 (19)	0.0405 (19)	0.0139 (14)	0.0083 (14)	0.0162 (16)
C3	0.0215 (16)	0.045 (2)	0.050 (2)	0.0054 (15)	−0.0015 (15)	0.0230 (18)
C4	0.0334 (17)	0.0335 (18)	0.0306 (18)	−0.0012 (14)	−0.0009 (14)	0.0122 (15)
C4A	0.0295 (16)	0.0273 (16)	0.0263 (16)	0.0053 (13)	0.0061 (13)	0.0125 (14)
C5	0.0345 (17)	0.0258 (16)	0.0269 (17)	0.0040 (13)	0.0020 (14)	0.0053 (13)
C6	0.0294 (16)	0.0240 (16)	0.0288 (17)	0.0070 (13)	0.0038 (13)	0.0074 (13)
C6A	0.0258 (15)	0.0264 (16)	0.0221 (15)	0.0082 (13)	0.0075 (13)	0.0090 (13)
C7A	0.0250 (15)	0.0325 (17)	0.0216 (16)	0.0116 (13)	0.0061 (13)	0.0122 (14)
C10	0.0237 (15)	0.0299 (16)	0.0242 (16)	0.0089 (13)	0.0082 (13)	0.0106 (13)
C10A	0.0232 (15)	0.0237 (15)	0.0184 (15)	0.0054 (12)	0.0045 (12)	0.0062 (12)
C11	0.0233 (14)	0.0264 (15)	0.0175 (14)	0.0122 (12)	0.0079 (12)	0.0088 (12)
C11A	0.0222 (14)	0.0235 (15)	0.0196 (15)	0.0062 (12)	0.0069 (12)	0.0093 (12)
C11B	0.0225 (14)	0.0259 (16)	0.0215 (15)	0.0058 (12)	0.0071 (12)	0.0098 (13)
C81	0.0317 (17)	0.0357 (18)	0.0220 (16)	0.0177 (14)	0.0051 (13)	0.0099 (14)
C82	0.0309 (17)	0.052 (2)	0.0260 (17)	0.0216 (15)	0.0089 (14)	0.0171 (15)
C83	0.0382 (18)	0.069 (3)	0.0233 (17)	0.0323 (18)	0.0090 (15)	0.0168 (17)
C84	0.059 (2)	0.050 (2)	0.0327 (19)	0.0386 (19)	0.0032 (17)	0.0092 (17)
C85	0.050 (2)	0.035 (2)	0.065 (3)	0.0171 (17)	−0.0050 (19)	0.0173 (19)
C86	0.0362 (18)	0.037 (2)	0.063 (2)	0.0182 (16)	0.0017 (17)	0.0191 (18)
C101	0.0249 (15)	0.0323 (18)	0.0368 (18)	0.0068 (13)	0.0060 (14)	0.0126 (15)
C111	0.0158 (13)	0.0250 (15)	0.0223 (15)	0.0048 (11)	0.0029 (12)	0.0072 (13)
C112	0.0260 (15)	0.0297 (17)	0.0202 (15)	0.0095 (13)	0.0042 (12)	0.0095 (13)
C113	0.0328 (16)	0.0261 (16)	0.0208 (15)	0.0118 (13)	0.0069 (13)	0.0052 (13)
C114	0.0224 (15)	0.0229 (15)	0.0277 (16)	0.0046 (12)	0.0028 (12)	0.0078 (13)
C115	0.0265 (15)	0.0257 (16)	0.0217 (15)	0.0035 (13)	0.0039 (12)	0.0099 (13)
C116	0.0219 (14)	0.0258 (16)	0.0194 (15)	0.0076 (12)	0.0044 (12)	0.0056 (12)

Geometric parameters (Å, º) top

C1—C2	1.381 (4)	C83—C84	1.383 (5)
C1—C11B	1.403 (4)	C83—H83	0.95
C1—H1	0.95	C84—C85	1.369 (5)
C2—C3	1.383 (4)	C84—H84	0.95
C2—H2	0.95	C85—C86	1.393 (4)
C3—C4	1.385 (4)	C85—H85	0.95
C3—H3	0.95	C86—H86	0.95
C4—C4A	1.392 (4)	N9—C10	1.318 (3)
C4—H4	0.95	C10—C10A	1.438 (4)
C4A—C11B	1.407 (4)	C10—C101	1.494 (4)
C4A—C5	1.501 (4)	C101—H10A	0.98
C5—C6	1.520 (4)	C101—H10B	0.98
C5—H5A	0.99	C101—H10C	0.98
C5—H5B	0.99	C10A—C11	1.413 (4)
C6—C6A	1.497 (4)	C11—C11A	1.398 (4)
C6—H6A	0.99	C11—C111	1.490 (4)
C6—H6B	0.99	C111—C116	1.390 (4)
C6A—N7	1.336 (3)	C111—C112	1.397 (4)
C6A—C11A	1.429 (4)	C112—C113	1.387 (4)
N7—C7A	1.342 (3)	C112—H112	0.95
C7A—N8	1.376 (3)	C113—C114	1.381 (4)
C7A—C10A	1.392 (4)	C113—H113	0.95
N8—N9	1.379 (3)	C114—C115	1.381 (4)
N8—C81	1.423 (3)	C114—Br14	1.894 (3)
C81—C86	1.373 (4)	C115—C116	1.382 (4)
C81—C82	1.388 (4)	C115—H115	0.95
C82—C83	1.385 (4)	C116—H116	0.95
C82—H82	0.95	C11A—C11B	1.495 (4)

C2—C1—C11B	121.4 (3)	C83—C84—H84	120.1
C2—C1—H1	119.3	C84—C85—C86	120.6 (3)
C11B—C1—H1	119.3	C84—C85—H85	119.7
C1—C2—C3	120.4 (3)	C86—C85—H85	119.7
C1—C2—H2	119.8	C81—C86—C85	119.4 (3)
C3—C2—H2	119.8	C81—C86—H86	120.3
C2—C3—C4	119.0 (3)	C85—C86—H86	120.3
C2—C3—H3	120.5	C10—N9—N8	107.3 (2)
C4—C3—H3	120.5	N9—C10—C10A	110.3 (2)
C3—C4—C4A	121.5 (3)	N9—C10—C101	119.1 (2)
C3—C4—H4	119.2	C10A—C10—C101	130.6 (3)
C4A—C4—H4	119.2	C10—C101—H10A	109.5
C4—C4A—C11B	119.6 (3)	C10—C101—H10B	109.5
C4—C4A—C5	121.7 (3)	H10A—C101—H10B	109.5
C11B—C4A—C5	118.7 (2)	C10—C101—H10C	109.5
C4A—C5—C6	109.6 (2)	H10A—C101—H10C	109.5
C4A—C5—H5A	109.8	H10B—C101—H10C	109.5
C6—C5—H5A	109.8	C7A—C10A—C11	118.5 (2)
C4A—C5—H5B	109.8	C7A—C10A—C10	105.0 (2)
C6—C5—H5B	109.8	C11—C10A—C10	136.4 (3)
H5A—C5—H5B	108.2	C11A—C11—C10A	116.8 (2)
C6A—C6—C5	109.5 (2)	C11A—C11—C111	124.5 (2)
C6A—C6—H6A	109.8	C10A—C11—C111	118.7 (2)
C5—C6—H6A	109.8	C116—C111—C112	118.9 (3)
C6A—C6—H6B	109.8	C116—C111—C11	120.9 (2)
C5—C6—H6B	109.8	C112—C111—C11	120.2 (2)
H6A—C6—H6B	108.2	C113—C112—C111	120.3 (2)
N7—C6A—C11A	125.1 (2)	C113—C112—H112	119.9
N7—C6A—C6	116.3 (2)	C111—C112—H112	119.9
C11A—C6A—C6	118.5 (2)	C114—C113—C112	119.5 (3)
C6A—N7—C7A	114.1 (2)	C114—C113—H113	120.3
N7—C7A—N8	126.1 (2)	C112—C113—H113	120.3
N7—C7A—C10A	126.7 (2)	C115—C114—C113	121.2 (3)
N8—C7A—C10A	107.2 (2)	C115—C114—Br14	120.2 (2)
C7A—N8—N9	110.2 (2)	C113—C114—Br14	118.6 (2)
C7A—N8—C81	130.0 (2)	C114—C115—C116	119.0 (2)
N9—N8—C81	119.8 (2)	C114—C115—H115	120.5
C86—C81—C82	120.6 (3)	C116—C115—H115	120.5
C86—C81—N8	120.2 (3)	C115—C116—C111	121.1 (3)
C82—C81—N8	119.3 (3)	C115—C116—H116	119.5
C83—C82—C81	119.3 (3)	C111—C116—H116	119.5
C83—C82—H82	120.4	C11—C11A—C6A	118.7 (2)
C81—C82—H82	120.4	C11—C11A—C11B	124.4 (2)
C84—C83—C82	120.4 (3)	C6A—C11A—C11B	116.9 (2)
C84—C83—H83	119.8	C1—C11B—C4A	117.9 (2)
C82—C83—H83	119.8	C1—C11B—C11A	123.1 (2)
C85—C84—C83	119.7 (3)	C4A—C11B—C11A	119.0 (2)
C85—C84—H84	120.1

C11B—C1—C2—C3	−0.7 (4)	C101—C10—C10A—C7A	−178.8 (3)
C1—C2—C3—C4	−2.3 (5)	N9—C10—C10A—C11	176.4 (3)
C2—C3—C4—C4A	2.1 (5)	C101—C10—C10A—C11	−2.9 (5)
C3—C4—C4A—C11B	1.2 (4)	C7A—C10A—C11—C11A	−1.7 (4)
C3—C4—C4A—C5	−177.9 (3)	C10—C10A—C11—C11A	−177.2 (3)
C4—C4A—C5—C6	142.4 (3)	C7A—C10A—C11—C111	176.9 (2)
C11B—C4A—C5—C6	−36.7 (3)	C10—C10A—C11—C111	1.4 (5)
C4A—C5—C6—C6A	58.3 (3)	C11A—C11—C111—C116	67.7 (3)
C5—C6—C6A—N7	140.1 (2)	C10A—C11—C111—C116	−110.7 (3)
C5—C6—C6A—C11A	−41.0 (3)	C11A—C11—C111—C112	−111.7 (3)
C11A—C6A—N7—C7A	−0.3 (4)	C10A—C11—C111—C112	69.8 (3)
C6—C6A—N7—C7A	178.5 (2)	C116—C111—C112—C113	−1.7 (4)
C6A—N7—C7A—N8	178.0 (3)	C11—C111—C112—C113	177.8 (2)
C6A—N7—C7A—C10A	0.9 (4)	C111—C112—C113—C114	−0.3 (4)
N7—C7A—N8—N9	−176.9 (2)	C112—C113—C114—C115	2.3 (4)
C10A—C7A—N8—N9	0.7 (3)	C112—C113—C114—Br14	−176.98 (19)
N7—C7A—N8—C81	0.2 (5)	C113—C114—C115—C116	−2.4 (4)
C10A—C7A—N8—C81	177.8 (3)	Br14—C114—C115—C116	176.94 (19)
C7A—N8—C81—C86	27.9 (5)	C114—C115—C116—C111	0.4 (4)
N9—N8—C81—C86	−155.2 (3)	C112—C111—C116—C115	1.6 (4)
C7A—N8—C81—C82	−152.9 (3)	C11—C111—C116—C115	−177.8 (2)
N9—N8—C81—C82	24.0 (4)	C10A—C11—C11A—C6A	2.2 (4)
C86—C81—C82—C83	−0.4 (4)	C111—C11—C11A—C6A	−176.3 (2)
N8—C81—C82—C83	−179.6 (3)	C10A—C11—C11A—C11B	−177.4 (2)
C81—C82—C83—C84	0.3 (4)	C111—C11—C11A—C11B	4.1 (4)
C82—C83—C84—C85	−0.6 (5)	N7—C6A—C11A—C11	−1.2 (4)
C83—C84—C85—C86	1.1 (5)	C6—C6A—C11A—C11	−180.0 (2)
C82—C81—C86—C85	0.9 (5)	N7—C6A—C11A—C11B	178.4 (2)
N8—C81—C86—C85	−180.0 (3)	C6—C6A—C11A—C11B	−0.4 (4)
C84—C85—C86—C81	−1.2 (6)	C2—C1—C11B—C4A	3.9 (4)
C7A—N8—N9—C10	−0.4 (3)	C2—C1—C11B—C11A	−176.0 (2)
C81—N8—N9—C10	−177.8 (2)	C4—C4A—C11B—C1	−4.1 (4)
N8—N9—C10—C10A	−0.1 (3)	C5—C4A—C11B—C1	175.1 (2)
N8—N9—C10—C101	179.3 (2)	C4—C4A—C11B—C11A	175.8 (2)
N7—C7A—C10A—C11	0.1 (4)	C5—C4A—C11B—C11A	−5.1 (4)
N8—C7A—C10A—C11	−177.5 (2)	C11—C11A—C11B—C1	24.6 (4)
N7—C7A—C10A—C10	176.9 (3)	C6A—C11A—C11B—C1	−155.0 (2)
N8—C7A—C10A—C10	−0.7 (3)	C11—C11A—C11B—C4A	−155.3 (3)
N9—C10—C10A—C7A	0.5 (3)	C6A—C11A—C11B—C4A	25.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C113—H113···Cg1ⁱ	0.95	2.71	3.588 (3)	154
C115—H115···Cg2ⁱⁱ	0.95	2.81	3.589 (3)	140

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

Acknowledgements

X-ray data were collected at the EPSRC X-ray Crystallographic Service, University of Southampton, England. JC thanks the Consejería de Innovación, Ciencia y Empresa (Junta de Andalucía, Spain) and the Universidad de Jaén for financial support. JQ and HS thank COLCIENCIAS and UNIVALLE (Universidad del Valle, Colombia) for financial support.

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