(3E)-3-[(4-Hexyl­phenyl)­imino]1H-indol-2(3H)-one

In the title compound, C₂₀H₂₂N₂O, the indole and hexyl­phenyl groups are connected by a C-N bond of 1.431 (2) Å. The mol­ecule is not planar.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.050
• wR factor = 0.132
• Data-to-parameter ratio = 12.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_369  Alert C Long   C(sp2)-C(sp2) Bond  C(1)   -   C(2)   =       1.53 Ang.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

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S1. Comment

The synthetic versality of isatin has lead to the extensive use of this compound in organic synthesis. It has stemmed from the interest in the biological and pharmacological properties of the derivatives (Silva et al., 2001; Pardasani et al., 1999). Isatin and derivatives of isatin have been used as reagents in the dye industry also. Although, it was firstly synthesized nearly hundred years ago, recently it was discovered in mamalian tissues and in body fluid. It was observed that monoamin oxidase was inhibited by isatin and derivatives in in vitro studies.

Schiff bases of isatin were reported to posses antibacterial (Sarangapani & Reddy, 1994; Varma & Nobles, 1975), antifungal (Pandeya et al., 1999), antiviral (Singh et al., 1983), anti-HIV (Pandeya et al., 2000), antiprotozoal (Varma & Khan, 1977) and antihelminthic (Sarciron et al., 1993) activities.

Our interest in this category of ligands is justified by their already proved medical and biological implications (Popp & Pajouhesh, 1982).

In this study, our purpose was to synthesize and characterize of a new Schiff base ligand, as shown in Fig 1. We reported analytical and X-ray crystallographic studies of the title compound, (I).

The C1—C2 bond length of 1.529 (3) Å is longer than the standard value for this type of bond (Allen et al., 1987). The C2—N2—C9 angle is 119.2 (2)°. In the hexyl group, the average value of the bond angle C—C—C is 115.2 (3)° and this group shows a zigzag form. The indol group is planar [maximum displacements are −0.025 (2) Å for C3 and 0.021 (2) Å for C7] and forms a dihedral angle of 88.01 (5)° with the phenyl plane.

To determine the structural and electronic parameters of the investigated isatin derivative, the conformational analyses of the compound and its quantum mechanic optimizations was performed.

The quantum-chemical calculation using the PM3 method showed that the charges at atoms N1, N2 and O1 are 0.0374, 0.0547 and −0.2933 e, respectively. The final heat of formation of the title compound is 5.53 kcal and its total energy is −3326.84 eV. The values of the HOMO and LUMO energies are −9.02078 and −1.05314 eV, respectively. The molecule dipole moment calculated is 4.467 Debye (one-dimensional = 3.33564 × 10⁻³⁰ Cm) for (I).

The crystal structure is stabilized by N—H···N and C—H···O hydrogen bonds (Fig. 2), the details of which are given in Table 2.

S2. Experimental

All chemicals used were at analytical purity, namely isatin, 4-butylaniline, phosphorus pentoxide. Ethanol and methanol was distilled and dried prior to use according to methods reported in the literature. The carbon, hydrogen, and nitrogen microanalyses were carried on a Carlo Erba 1106 elemental analyser. The Fourier transformation IR spectra (FT–IR) were recorded with Unicam Mattson 1000 F T–IR spectrophotometer (in the range 400–4000 cm⁻¹), using KBr pellet (1 mg per 100 mg) technique. The electronic spectra were recorded on a Philips PU 8700 spectrophotometer (in the region 190–700 nm) using 10⁻³ mol dm⁻³ solution in DMF and ethanol. ¹H NMR data were recorded on Bruker AC 200 L. The free ligand, Schiff base, was sythesized by usual condensation reaction. The preparation of the Schiff base was conducted as follows: an ethanol solution of isatin (0.001 mol per 25 ml) was added to an ethanol solution of 4-hexylaniline (0.001 mol per 25 ml) and refluxed for 4 h on a water bath. After solution concentration, the precipitate was separated by suction filtration, washed with ethanol and dried over P₂O₅ in vacuum. The orange product was recrystallized from methanol. Colours, yields, melting point, and analytical data are as follows: C₂₀H₂₂N₂O, orange, yield 75–80%, m.p. 456 K. Analysis calculated: C 78.30, H 6.98, N 9.20%; found: C 78.43, H 7.19, N 9.15%. λ_max (DMF, nm): 328 440 The IR spectral data of the title compound [frequency (cm⁻¹), KBr]: 3182 (NH), 2927–2851 (Ar—H3), 1753 (C═O), 1651 (C═N), 1600 (C═C). ¹H NMR (D₂O, d, p.p.m.) spectral data of the title compound: 0.85 (m, 3H, CH₃), 1.23 (s, 6H, –CH₂–), 1.62 (m, 2H, –CH₂–), 2.6 (m, 2H, –CH₂), 6.42–6.65 (two symmetric m, 2H, Ar–H), 7.00–7.40 (two m, 4H, Ar—H), 10.98 (s, 1H, NH).

S3. Refinement

All H atoms were located geometrically and their coordinates refined isotropically.

Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: EVALCCD (Duisenberg, 1998); data reduction: EVALCCD; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

	Fig. 1. An ORTEP-3 (Farrugia, 1997) drawing of the title compound, showing the labelling of the non-H atoms. Displacement ellipsoids are shown at the 50% probability level.
	Fig. 2. A view of the crystal packing and the short hydrogen-bond contacts.

(I)

Crystal data

C20H22N2O	F(000) = 656
Mr = 306.40	Dx = 1.198 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 155 reflections
a = 17.1506 (2) Å	θ = 6.0–20.0°
b = 9.6464 (2) Å	µ = 0.07 mm^−1
c = 10.4167 (2) Å	T = 294 K
β = 99.693 (2)°	Plate, orange
V = 1698.75 (5) Å^3	0.52 × 0.31 × 0.05 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	2121 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.089
Graphite monochromator	θmax = 26.0°, θmin = 3.6°
Detector resolution: 9 pixels mm^-1	h = −21→21
ϕ– and ω–scans with 2.0 ° and 120 second per frame	k = −11→11
30666 measured reflections	l = −12→12
3326 independent 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.132	Only H-atom coordinates refined
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0575P)^2 + 0.3745P] where P = (Fo^2 + 2Fc^2)/3
3326 reflections	(Δ/σ)max < 0.001
274 parameters	Δρmax = 0.14 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F^{2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F}2, conventional R-factors R are based on F, with F set to zero for negative F^{2. The observed criterion of F}2 > σ(F^{2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F}2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
O1	−0.00779 (9)	0.45436 (15)	−0.33365 (15)	0.0620 (6)
N1	0.01978 (9)	0.61028 (17)	−0.16356 (17)	0.0466 (6)
N2	0.11124 (9)	0.28834 (16)	−0.18012 (16)	0.0473 (6)
C1	0.02712 (11)	0.4898 (2)	−0.2277 (2)	0.0439 (7)
C2	0.09157 (10)	0.40710 (19)	−0.14094 (18)	0.0400 (6)
C3	0.11827 (10)	0.49415 (18)	−0.02711 (18)	0.0384 (6)
C4	0.07286 (10)	0.61641 (19)	−0.04482 (19)	0.0410 (6)
C5	0.08244 (13)	0.7210 (2)	0.0463 (2)	0.0520 (8)
C6	0.13775 (13)	0.7005 (2)	0.1585 (2)	0.0539 (8)
C7	0.18189 (13)	0.5795 (2)	0.1796 (2)	0.0515 (7)
C8	0.17223 (11)	0.4752 (2)	0.0866 (2)	0.0460 (7)
C9	0.17748 (11)	0.21715 (18)	−0.10721 (18)	0.0424 (6)
C10	0.25233 (12)	0.2453 (2)	−0.1352 (2)	0.0529 (7)
C11	0.31742 (13)	0.1745 (2)	−0.0713 (2)	0.0542 (8)
C12	0.31026 (12)	0.07424 (19)	0.0215 (2)	0.0468 (7)
C13	0.23480 (12)	0.0461 (2)	0.0461 (2)	0.0507 (7)
C14	0.16877 (12)	0.1156 (2)	−0.0174 (2)	0.0504 (7)
C15	0.38268 (14)	0.0019 (2)	0.0943 (3)	0.0582 (8)
C16	0.43551 (14)	0.0953 (2)	0.1882 (3)	0.0631 (9)
C17	0.50672 (14)	0.0243 (3)	0.2667 (3)	0.0615 (9)
C18	0.55691 (15)	0.1160 (3)	0.3641 (3)	0.0691 (9)
C19	0.62297 (16)	0.0458 (3)	0.4525 (3)	0.0746 (10)
C20	0.67233 (18)	0.1385 (4)	0.5500 (3)	0.0807 (11)
H1	−0.0165 (15)	0.672 (3)	−0.193 (2)	0.0800*
H5	0.0509 (14)	0.804 (3)	0.034 (2)	0.0800*
H6	0.1463 (14)	0.775 (3)	0.226 (2)	0.0800*
H7	0.2209 (14)	0.568 (2)	0.262 (2)	0.0800*
H8	0.2037 (14)	0.393 (3)	0.102 (2)	0.0800*
H10	0.2591 (14)	0.312 (3)	−0.198 (2)	0.0800*
H11	0.3712 (15)	0.194 (2)	−0.096 (2)	0.0800*
H13	0.2271 (14)	−0.023 (3)	0.110 (2)	0.0800*
H14	0.1163 (15)	0.095 (2)	−0.002 (2)	0.0800*
H15A	0.3649 (14)	−0.075 (3)	0.143 (2)	0.0800*
H15B	0.4138 (14)	−0.040 (3)	0.030 (2)	0.0800*
H16A	0.4542 (14)	0.171 (3)	0.141 (2)	0.0800*
H16B	0.4028 (14)	0.139 (3)	0.250 (2)	0.0800*
H17A	0.4876 (14)	−0.054 (3)	0.314 (2)	0.0800*
H17B	0.5355 (15)	−0.025 (3)	0.213 (3)	0.0800*
H18A	0.5811 (14)	0.185 (3)	0.310 (2)	0.0800*
H18B	0.5261 (15)	0.166 (3)	0.413 (2)	0.0800*
H19A	0.6549 (15)	−0.004 (3)	0.400 (2)	0.0800*
H19B	0.5964 (14)	−0.031 (3)	0.496 (2)	0.0800*
H20A	0.6414 (15)	0.189 (3)	0.602 (2)	0.0800*
H20B	0.7142 (15)	0.084 (3)	0.613 (2)	0.0800*
H20C	0.7006 (14)	0.211 (3)	0.500 (2)	0.0800*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0568 (9)	0.0638 (10)	0.0562 (10)	0.0018 (7)	−0.0170 (8)	0.0027 (8)
N1	0.0405 (9)	0.0429 (10)	0.0534 (11)	0.0068 (7)	−0.0008 (8)	0.0087 (8)
N2	0.0433 (9)	0.0434 (10)	0.0502 (10)	0.0000 (8)	−0.0062 (8)	−0.0018 (8)
C1	0.0363 (10)	0.0447 (12)	0.0480 (12)	−0.0055 (8)	−0.0005 (9)	0.0080 (10)
C2	0.0343 (9)	0.0394 (11)	0.0444 (11)	−0.0031 (8)	0.0013 (8)	0.0051 (9)
C3	0.0338 (9)	0.0385 (10)	0.0420 (11)	−0.0022 (8)	0.0034 (8)	0.0047 (9)
C4	0.0360 (10)	0.0411 (11)	0.0455 (12)	−0.0015 (8)	0.0057 (9)	0.0081 (9)
C5	0.0540 (13)	0.0432 (12)	0.0595 (14)	0.0053 (10)	0.0116 (11)	0.0007 (11)
C6	0.0568 (13)	0.0522 (13)	0.0527 (13)	−0.0004 (10)	0.0093 (11)	−0.0069 (11)
C7	0.0520 (12)	0.0553 (13)	0.0448 (13)	−0.0008 (10)	0.0016 (10)	−0.0005 (10)
C8	0.0412 (11)	0.0474 (12)	0.0468 (12)	0.0012 (9)	−0.0002 (10)	0.0027 (10)
C9	0.0443 (11)	0.0331 (10)	0.0451 (12)	0.0010 (8)	−0.0061 (9)	−0.0059 (9)
C10	0.0500 (12)	0.0446 (12)	0.0614 (14)	−0.0011 (10)	0.0015 (10)	0.0087 (10)
C11	0.0432 (12)	0.0519 (12)	0.0657 (15)	0.0023 (10)	0.0042 (11)	0.0055 (11)
C12	0.0499 (12)	0.0347 (10)	0.0516 (12)	0.0028 (9)	−0.0037 (10)	−0.0055 (9)
C13	0.0559 (13)	0.0423 (12)	0.0499 (13)	−0.0044 (10)	−0.0026 (10)	0.0045 (10)
C14	0.0451 (12)	0.0522 (13)	0.0508 (13)	−0.0046 (10)	−0.0013 (10)	0.0023 (10)
C15	0.0570 (13)	0.0448 (12)	0.0677 (16)	0.0117 (10)	−0.0044 (12)	0.0005 (12)
C16	0.0582 (14)	0.0485 (13)	0.0741 (17)	0.0082 (11)	−0.0130 (12)	−0.0014 (12)
C17	0.0513 (13)	0.0580 (14)	0.0708 (17)	0.0096 (11)	−0.0024 (12)	0.0028 (13)
C18	0.0591 (15)	0.0583 (15)	0.0820 (19)	0.0005 (12)	−0.0107 (13)	0.0087 (14)
C19	0.0537 (14)	0.0826 (19)	0.082 (2)	0.0088 (13)	−0.0047 (14)	0.0044 (16)
C20	0.0630 (17)	0.097 (2)	0.075 (2)	0.0033 (15)	−0.0093 (14)	0.0049 (17)

Geometric parameters (Å, º)

O1—C1	1.213 (3)	C18—C19	1.496 (4)
N1—C1	1.357 (3)	C19—C20	1.503 (4)
N1—C4	1.408 (3)	C5—H5	0.96 (3)
N2—C2	1.280 (2)	C6—H6	1.00 (3)
N2—C9	1.431 (2)	C7—H7	1.00 (2)
N1—H1	0.88 (3)	C8—H8	0.96 (3)
C1—C2	1.529 (3)	C10—H10	0.94 (3)
C2—C3	1.462 (3)	C11—H11	1.02 (3)
C3—C8	1.387 (3)	C13—H13	0.97 (2)
C3—C4	1.408 (3)	C14—H14	0.96 (3)
C4—C5	1.376 (3)	C15—H15A	0.98 (3)
C5—C6	1.390 (3)	C15—H15B	1.01 (2)
C6—C7	1.388 (3)	C16—H16A	0.96 (3)
C7—C8	1.387 (3)	C16—H16B	1.01 (2)
C9—C10	1.390 (3)	C17—H17A	0.99 (3)
C9—C14	1.380 (3)	C17—H17B	0.94 (3)
C10—C11	1.380 (3)	C18—H18A	1.01 (3)
C11—C12	1.387 (3)	C18—H18B	0.93 (3)
C12—C13	1.388 (3)	C19—H19A	0.96 (3)
C12—C15	1.512 (3)	C19—H19B	1.02 (3)
C13—C14	1.385 (3)	C20—H20A	0.95 (3)
C15—C16	1.514 (4)	C20—H20B	1.03 (3)
C16—C17	1.514 (4)	C20—H20C	1.04 (3)
C17—C18	1.503 (4)
O1···N2	2.862 (2)	H1···N2^ii	2.22 (3)
O1···C5^i	3.265 (3)	H1···C2^ii	3.01 (3)
O1···C14^ii	3.318 (3)	H5···O1^ii	2.55 (2)
O1···H1^i	2.76 (3)	H6···N1^ix	2.85 (2)
O1···H5^i	2.55 (2)	H6···C4^ix	3.07 (2)
O1···H14^ii	2.68 (2)	H8···C9	2.74 (2)
N1···N2^ii	3.069 (2)	H8···C10	3.09 (2)
N2···O1	2.862 (2)	H8···C14	2.97 (3)
N2···N1^i	3.069 (2)	H8···C10^viii	3.03 (2)
N1···H6^iii	2.85 (2)	H10···C13^vii	2.96 (2)
N2···H1^i	2.22 (2)	H11···H16B^vii	2.40 (3)
C1···C5^iv	3.526 (3)	H13···H15A	2.38 (3)
C1···C6^iv	3.546 (3)	H14···O1^i	2.68 (2)
C2···C5^iv	3.521 (3)	H15A···H13	2.38 (3)
C4···C4^iv	3.598 (3)	H15A···H17A	2.53 (3)
C5···C2^iv	3.521 (3)	H15A···H18A^vi	2.51 (4)
C5···O1^ii	3.265 (3)	H15B···H17B	2.58 (4)
C5···C1^iv	3.526 (3)	H16A···C11	2.94 (2)
C6···C1^iv	3.546 (3)	H16A···H18A	2.56 (3)
C8···C20^v	3.590 (4)	H16B···H18B	2.49 (3)
C8···C9	3.216 (3)	H16B···H11^viii	2.40 (3)
C9···C8	3.216 (3)	H17A···H15A	2.53 (3)
C14···O1^i	3.318 (3)	H17A···H19B	2.44 (3)
C20···C8^vi	3.590 (4)	H17B···H15B	2.58 (4)
C2···H1^i	3.01 (3)	H17B···H19A	2.59 (4)
C4···H6^iii	3.07 (2)	H18A···H16A	2.56 (3)
C8···H19A^v	2.95 (3)	H18A···H15A^v	2.51 (4)
C9···H8	2.74 (2)	H18B···H16B	2.49 (3)
C10···H8^vii	3.03 (2)	H18B···H20A	2.55 (3)
C10···H8	3.09 (2)	H19A···H17B	2.59 (4)
C11···H16A	2.94 (2)	H19A···C8^vi	2.95 (3)
C13···H10^viii	2.96 (2)	H19B···H17A	2.44 (3)
C14···H8	2.97 (3)	H20A···H18B	2.55 (3)
H1···O1^ii	2.76 (3)
C1—N1—C4	111.63 (16)	C3—C8—H8	121.9 (13)
C2—N2—C9	119.23 (16)	C7—C8—H8	119.1 (14)
C1—N1—H1	121.8 (16)	C9—C10—H10	120.5 (15)
C4—N1—H1	126.4 (15)	C11—C10—H10	119.4 (15)
N1—C1—C2	105.88 (16)	C10—C11—H11	118.8 (12)
O1—C1—C2	125.99 (18)	C12—C11—H11	119.7 (12)
O1—C1—N1	128.10 (19)	C12—C13—H13	120.1 (15)
N2—C2—C3	135.16 (17)	C14—C13—H13	117.9 (15)
C1—C2—C3	106.03 (15)	C9—C14—H14	118.1 (12)
N2—C2—C1	118.78 (17)	C13—C14—H14	122.3 (12)
C4—C3—C8	119.80 (17)	C12—C15—H15A	108.0 (14)
C2—C3—C4	106.50 (16)	C12—C15—H15B	109.5 (13)
C2—C3—C8	133.60 (17)	C16—C15—H15A	108.8 (13)
C3—C4—C5	121.64 (18)	C16—C15—H15B	110.0 (14)
N1—C4—C3	109.96 (16)	H15A—C15—H15B	107 (2)
N1—C4—C5	128.40 (17)	C15—C16—H16A	109.6 (14)
C4—C5—C6	117.46 (18)	C15—C16—H16B	108.8 (14)
C5—C6—C7	121.97 (19)	C17—C16—H16A	108.1 (14)
C6—C7—C8	120.09 (19)	C17—C16—H16B	109.1 (13)
C3—C8—C7	119.00 (18)	H16A—C16—H16B	106 (2)
C10—C9—C14	119.34 (18)	C16—C17—H17A	108.1 (14)
N2—C9—C14	122.24 (17)	C16—C17—H17B	111.5 (18)
N2—C9—C10	118.26 (16)	C18—C17—H17A	108.3 (13)
C9—C10—C11	120.17 (18)	C18—C17—H17B	113.8 (17)
C10—C11—C12	121.4 (2)	H17A—C17—H17B	99 (2)
C13—C12—C15	121.99 (19)	C17—C18—H18A	104.8 (13)
C11—C12—C13	117.37 (19)	C17—C18—H18B	111.2 (16)
C11—C12—C15	120.63 (19)	C19—C18—H18A	107.7 (14)
C12—C13—C14	122.02 (19)	C19—C18—H18B	109.8 (14)
C9—C14—C13	119.63 (19)	H18A—C18—H18B	107 (2)
C12—C15—C16	113.65 (17)	C18—C19—H19A	108.6 (14)
C15—C16—C17	114.86 (19)	C18—C19—H19B	104.7 (14)
C16—C17—C18	114.6 (2)	C20—C19—H19A	111.7 (15)
C17—C18—C19	115.9 (2)	C20—C19—H19B	112.1 (13)
C18—C19—C20	115.4 (3)	H19A—C19—H19B	103 (2)
C4—C5—H5	121.3 (13)	C19—C20—H20A	112.6 (16)
C6—C5—H5	121.3 (13)	C19—C20—H20B	112.3 (16)
C5—C6—H6	119.2 (14)	C19—C20—H20C	108.6 (13)
C7—C6—H6	118.8 (14)	H20A—C20—H20B	107.1 (19)
C6—C7—H7	119.8 (12)	H20A—C20—H20C	107 (2)
C8—C7—H7	120.1 (12)	H20B—C20—H20C	109 (2)
C4—N1—C1—O1	−177.4 (2)	N1—C4—C5—C6	178.12 (19)
C4—N1—C1—C2	0.6 (2)	C3—C4—C5—C6	−1.3 (3)
C1—N1—C4—C3	−0.2 (2)	C4—C5—C6—C7	−0.3 (3)
C1—N1—C4—C5	−179.7 (2)	C5—C6—C7—C8	0.8 (3)
C9—N2—C2—C1	172.88 (16)	C6—C7—C8—C3	0.2 (3)
C9—N2—C2—C3	−4.7 (3)	N2—C9—C10—C11	−177.12 (17)
C2—N2—C9—C10	−87.2 (2)	C10—C9—C14—C13	1.8 (3)
C2—N2—C9—C14	97.3 (2)	C14—C9—C10—C11	−1.6 (3)
O1—C1—C2—C3	177.31 (19)	N2—C9—C14—C13	177.20 (18)
N1—C1—C2—N2	−178.96 (17)	C9—C10—C11—C12	0.1 (3)
N1—C1—C2—C3	−0.7 (2)	C10—C11—C12—C15	−177.5 (2)
O1—C1—C2—N2	−0.9 (3)	C10—C11—C12—C13	1.1 (3)
C1—C2—C3—C8	176.9 (2)	C11—C12—C13—C14	−0.8 (3)
C1—C2—C3—C4	0.61 (19)	C15—C12—C13—C14	177.8 (2)
N2—C2—C3—C4	178.4 (2)	C11—C12—C15—C16	69.0 (3)
N2—C2—C3—C8	−5.3 (4)	C13—C12—C15—C16	−109.6 (2)
C2—C3—C4—C5	179.23 (18)	C12—C13—C14—C9	−0.6 (3)
C8—C3—C4—N1	−177.19 (17)	C12—C15—C16—C17	177.5 (2)
C8—C3—C4—C5	2.3 (3)	C15—C16—C17—C18	−177.3 (2)
C2—C3—C8—C7	−177.6 (2)	C16—C17—C18—C19	174.0 (2)
C2—C3—C4—N1	−0.3 (2)	C17—C18—C19—C20	−179.6 (2)
C4—C3—C8—C7	−1.7 (3)

Symmetry codes: (i) −x, y−1/2, −z−1/2; (ii) −x, y+1/2, −z−1/2; (iii) x, −y+3/2, z−1/2; (iv) −x, −y+1, −z; (v) −x+1, y+1/2, −z+1/2; (vi) −x+1, y−1/2, −z+1/2; (vii) x, −y+1/2, z−1/2; (viii) x, −y+1/2, z+1/2; (ix) x, −y+3/2, z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2^ii	0.88 (3)	2.22 (3)	3.069 (2)	163 (2)
C5—H5···O1^ii	0.96 (3)	2.55 (2)	3.265 (3)	131.4 (16)

Symmetry code: (ii) −x, y+1/2, −z−1/2.