3,3,6,6-Tetra-methyl-9-(1-methyl-1H-indol-2-yl)-1,2,3,4,5,6,7,8,9,10-deca-hydro-acridine-1,8-dione.

In the acridine system of the title mol-ecule, C26H30N2O2, both cyclo-hex-2-enone rings adopt sofa conformations. The indole ring system is essentially planar, with a maximum deviation of 0.017 (2) Å for a bridgehead C atom. An intra-molecular C-H⋯O hydrogen bond occurs. The mol-ecules assemble into C(6) chains in the crystal by way of N-H⋯O hydrogen bonds.

Related literature

For potassium channel modulator activity for bicyclo (quinoline) and tricyclo (acridine) analogs, see: Horiuchi et al. (2001 ▶); Crestanello et al. (2000 ▶); Frank et al. (1993 ▶); Berkan et al. (2002 ▶); Şimşek et al. (2004 ▶); Fincan et al. (2012 ▶); Gündüz et al. (2009 ▶); Li et al. (2011 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For a similar structure, see: El-Khouly et al. (2012 ▶). For geometric analysis, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Etter et al. (1990 ▶).

Experimental

Crystal data

C26H30N2O2

M = 402.54

Orthorhombic,

a = 14.09072 (13) Å

b = 15.04800 (15) Å

c = 10.39178 (12) Å

V = 2203.44 (4) Å3

Z = 4

Cu Kα radiation

μ = 0.60 mm−1

T = 123 K

0.50 × 0.45 × 0.40 mm

Data collection

Agilent Xcalibur (Ruby, Gemini) diffractometer

Absorption correction: multi-scan [CrysAlis RED (Agilent, 2011 ▶), based on expressions derived from Clark & Reid (1995 ▶)] T min = 0.753, T max = 0.795

10170 measured reflections

3713 independent reflections

3682 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.096

S = 1.02

3713 reflections

276 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812045722/jj2157sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812045722/jj2157Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812045722/jj2157Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C26H30N2O2	F(000) = 864
Mr = 402.54	Dx = 1.213 Mg m−3
Orthorhombic, Pna21	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2c -2n	Cell parameters from 8837 reflections
a = 14.09072 (13) Å	θ = 2.9–75.6°
b = 15.04800 (15) Å	µ = 0.60 mm−1
c = 10.39178 (12) Å	T = 123 K
V = 2203.44 (4) Å3	Block, colorless
Z = 4	0.50 × 0.45 × 0.40 mm

Agilent Xcalibur (Ruby, Gemini) diffractometer	3713 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3682 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
Detector resolution: 10.5081 pixels mm-1	θmax = 75.7°, θmin = 4.3°
ω scans	h = −17→17
Absorption correction: multi-scan [CrysAlis RED (Agilent, 2011), based on expressions derived from Clark & Reid (1995)]	k = −16→18
Tmin = 0.753, Tmax = 0.795	l = −13→8
10170 measured reflections

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)] = 0.036	H-atom parameters constrained
wR(F2) = 0.096	w = 1/[σ2(Fo2) + (0.0699P)2 + 0.2623P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
3713 reflections	Δρmax = 0.21 e Å−3
276 parameters	Δρmin = −0.24 e Å−3
1 restraint	Absolute structure: Flack (1983), 1302 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.17 (19)

Experimental. Absorption correction: CrysAlis RED, (Agilent, 2011) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. (Clark & Reid, 1995).

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O1	0.75903 (7)	0.25747 (7)	−0.00557 (13)	0.0295 (3)
O2	0.88973 (8)	0.50670 (7)	0.28897 (12)	0.0327 (3)
N1	1.08387 (8)	0.31288 (8)	0.04851 (15)	0.0286 (3)
H1A	1.1423	0.2968	0.0295	0.034*
N2	0.76168 (8)	0.31668 (8)	0.29367 (15)	0.0277 (3)
C1	1.01031 (10)	0.26736 (8)	−0.00433 (16)	0.0237 (3)
C2	1.03649 (10)	0.19916 (9)	−0.10381 (18)	0.0282 (3)
H2A	1.0974	0.1711	−0.0791	0.034*
H2B	1.0460	0.2292	−0.1876	0.034*
C3	0.96102 (10)	0.12665 (9)	−0.11949 (17)	0.0265 (3)
C4	0.86446 (10)	0.17241 (10)	−0.13694 (17)	0.0284 (3)
H4A	0.8635	0.2026	−0.2216	0.034*
H4B	0.8141	0.1265	−0.1375	0.034*
C5	0.84223 (10)	0.23979 (9)	−0.03302 (16)	0.0236 (3)
C6	0.91909 (10)	0.28578 (9)	0.02966 (15)	0.0222 (3)
C7	0.89455 (9)	0.35180 (9)	0.13511 (15)	0.0227 (3)
H7A	0.8458	0.3941	0.1013	0.027*
C8	0.98218 (10)	0.40439 (9)	0.17348 (16)	0.0240 (3)
C9	0.96904 (11)	0.48130 (9)	0.25718 (16)	0.0261 (3)
C10	1.05765 (12)	0.52769 (11)	0.30610 (18)	0.0332 (3)
H10A	1.0796	0.4973	0.3852	0.040*
H10B	1.0413	0.5896	0.3294	0.040*
C11	1.13923 (10)	0.52915 (9)	0.20810 (17)	0.0284 (3)
C12	1.15872 (10)	0.43298 (10)	0.16739 (19)	0.0319 (4)
H12A	1.2028	0.4331	0.0932	0.038*
H12B	1.1903	0.4014	0.2392	0.038*
C13	1.06997 (10)	0.38350 (9)	0.13094 (17)	0.0256 (3)
C14	0.85201 (10)	0.30123 (9)	0.24773 (16)	0.0245 (3)
C15	0.89064 (10)	0.23076 (9)	0.31221 (17)	0.0275 (3)
H15A	0.9521	0.2065	0.2990	0.033*
C16	0.82205 (11)	0.20026 (10)	0.40284 (17)	0.0294 (3)
C17	0.81850 (14)	0.13028 (12)	0.49248 (19)	0.0380 (4)
H17A	0.8712	0.0916	0.5031	0.046*
C18	0.73717 (15)	0.11860 (13)	0.5648 (2)	0.0441 (4)
H18A	0.7344	0.0715	0.6256	0.053*
C19	0.65921 (14)	0.17453 (13)	0.5502 (2)	0.0436 (4)
H19A	0.6044	0.1648	0.6014	0.052*
C20	0.65970 (13)	0.24415 (12)	0.4624 (2)	0.0385 (4)
H20A	0.6064	0.2822	0.4527	0.046*
C21	0.74192 (11)	0.25582 (10)	0.38884 (18)	0.0290 (3)
C22	0.69626 (11)	0.38452 (11)	0.2494 (2)	0.0374 (4)
H22A	0.6359	0.3787	0.2955	0.056*
H22B	0.6853	0.3773	0.1568	0.056*
H22C	0.7234	0.4434	0.2659	0.056*
C23	1.22930 (12)	0.56706 (11)	0.2695 (2)	0.0402 (4)
H23A	1.2813	0.5651	0.2070	0.060*
H23B	1.2462	0.5316	0.3451	0.060*
H23C	1.2180	0.6287	0.2956	0.060*
C24	1.11188 (12)	0.58625 (11)	0.09208 (19)	0.0368 (4)
H24A	1.1637	0.5857	0.0292	0.055*
H24B	1.1002	0.6474	0.1204	0.055*
H24D	1.0542	0.5622	0.0524	0.055*
C25	0.98527 (11)	0.07126 (11)	−0.2383 (2)	0.0358 (4)
H25A	0.9907	0.1103	−0.3133	0.054*
H25D	0.9350	0.0275	−0.2533	0.054*
H25B	1.0457	0.0404	−0.2243	0.054*
C26	0.95850 (13)	0.06656 (10)	−0.00001 (19)	0.0364 (4)
H26D	1.0207	0.0385	0.0117	0.055*
H26A	0.9101	0.0205	−0.0116	0.055*
H26B	0.9432	0.1023	0.0760	0.055*

	U11	U22	U33	U12	U13	U23
O1	0.0178 (5)	0.0333 (5)	0.0374 (7)	−0.0021 (4)	0.0009 (5)	0.0032 (5)
O2	0.0318 (6)	0.0337 (5)	0.0325 (7)	0.0063 (4)	0.0036 (5)	−0.0037 (5)
N1	0.0146 (5)	0.0261 (5)	0.0450 (9)	0.0008 (4)	0.0005 (6)	−0.0079 (5)
N2	0.0213 (5)	0.0287 (6)	0.0329 (8)	0.0027 (5)	0.0063 (5)	0.0026 (5)
C1	0.0196 (6)	0.0204 (6)	0.0312 (8)	0.0003 (5)	0.0001 (6)	−0.0004 (6)
C2	0.0200 (6)	0.0290 (6)	0.0355 (9)	−0.0012 (5)	0.0032 (6)	−0.0067 (6)
C3	0.0241 (6)	0.0248 (6)	0.0305 (8)	−0.0027 (5)	−0.0007 (7)	−0.0024 (6)
C4	0.0242 (6)	0.0317 (7)	0.0294 (9)	−0.0047 (5)	−0.0036 (6)	−0.0016 (6)
C5	0.0196 (6)	0.0253 (6)	0.0260 (8)	−0.0007 (5)	0.0003 (6)	0.0065 (5)
C6	0.0195 (6)	0.0227 (6)	0.0244 (8)	−0.0012 (5)	−0.0004 (5)	0.0017 (5)
C7	0.0171 (6)	0.0213 (6)	0.0297 (8)	0.0020 (4)	0.0012 (5)	0.0008 (5)
C8	0.0216 (6)	0.0221 (6)	0.0282 (8)	−0.0004 (5)	−0.0009 (6)	0.0012 (5)
C9	0.0285 (7)	0.0264 (6)	0.0235 (7)	0.0023 (5)	0.0008 (6)	0.0009 (6)
C10	0.0355 (8)	0.0356 (8)	0.0285 (9)	−0.0028 (6)	0.0002 (7)	−0.0097 (6)
C11	0.0256 (7)	0.0267 (6)	0.0328 (9)	−0.0039 (5)	−0.0021 (7)	−0.0059 (6)
C12	0.0201 (6)	0.0290 (7)	0.0467 (10)	−0.0005 (5)	−0.0030 (7)	−0.0081 (7)
C13	0.0208 (6)	0.0228 (6)	0.0333 (8)	−0.0004 (5)	−0.0017 (6)	−0.0023 (6)
C14	0.0195 (6)	0.0261 (6)	0.0279 (8)	0.0021 (5)	0.0014 (6)	−0.0025 (6)
C15	0.0251 (7)	0.0285 (7)	0.0288 (8)	0.0036 (5)	−0.0019 (6)	0.0012 (6)
C16	0.0291 (7)	0.0311 (7)	0.0279 (8)	−0.0032 (5)	−0.0033 (7)	−0.0012 (6)
C17	0.0448 (9)	0.0372 (8)	0.0321 (9)	−0.0042 (7)	−0.0083 (8)	0.0059 (7)
C18	0.0568 (11)	0.0448 (9)	0.0307 (10)	−0.0167 (8)	−0.0032 (9)	0.0093 (7)
C19	0.0450 (9)	0.0533 (10)	0.0324 (10)	−0.0181 (8)	0.0081 (8)	0.0021 (8)
C20	0.0319 (8)	0.0452 (8)	0.0383 (11)	−0.0054 (6)	0.0069 (8)	−0.0015 (8)
C21	0.0284 (7)	0.0299 (6)	0.0287 (8)	−0.0052 (5)	0.0003 (7)	−0.0010 (6)
C22	0.0256 (7)	0.0363 (7)	0.0504 (11)	0.0100 (6)	0.0095 (8)	0.0088 (7)
C23	0.0341 (8)	0.0393 (8)	0.0471 (11)	−0.0082 (7)	−0.0072 (8)	−0.0134 (8)
C24	0.0383 (8)	0.0346 (7)	0.0375 (10)	−0.0090 (6)	−0.0005 (8)	0.0030 (7)
C25	0.0306 (7)	0.0374 (8)	0.0395 (10)	−0.0054 (6)	0.0015 (8)	−0.0120 (7)
C26	0.0456 (9)	0.0249 (7)	0.0386 (10)	0.0024 (6)	0.0000 (8)	0.0028 (6)

O1—C5	1.2356 (18)	C11—C12	1.5325 (19)
O2—C9	1.2265 (18)	C12—C13	1.5039 (18)
N1—C1	1.3583 (19)	C12—H12A	0.9900
N1—C13	1.3789 (19)	C12—H12B	0.9900
N1—H1A	0.8800	C14—C15	1.368 (2)
N2—C21	1.376 (2)	C15—C16	1.425 (2)
N2—C14	1.3790 (18)	C15—H15A	0.9500
N2—C22	1.4505 (19)	C16—C17	1.407 (2)
C1—C6	1.3614 (19)	C16—C21	1.413 (2)
C1—C2	1.503 (2)	C17—C18	1.382 (3)
C2—C3	1.5323 (18)	C17—H17A	0.9500
C2—H2A	0.9900	C18—C19	1.392 (3)
C2—H2B	0.9900	C18—H18A	0.9500
C3—C25	1.528 (2)	C19—C20	1.389 (3)
C3—C4	1.5357 (19)	C19—H19A	0.9500
C3—C26	1.536 (2)	C20—C21	1.399 (2)
C4—C5	1.514 (2)	C20—H20A	0.9500
C4—H4A	0.9900	C22—H22A	0.9800
C4—H4B	0.9900	C22—H22B	0.9800
C5—C6	1.441 (2)	C22—H22C	0.9800
C6—C7	1.519 (2)	C23—H23A	0.9800
C7—C14	1.519 (2)	C23—H23B	0.9800
C7—C8	1.5199 (18)	C23—H23C	0.9800
C7—H7A	1.0000	C24—H24A	0.9800
C8—C13	1.351 (2)	C24—H24B	0.9800
C8—C9	1.459 (2)	C24—H24D	0.9800
C9—C10	1.518 (2)	C25—H25A	0.9800
C10—C11	1.536 (2)	C25—H25D	0.9800
C10—H10A	0.9900	C25—H25B	0.9800
C10—H10B	0.9900	C26—H26D	0.9800
C11—C24	1.530 (2)	C26—H26A	0.9800
C11—C23	1.531 (2)	C26—H26B	0.9800
C1—N1—C13	122.10 (12)	C13—C12—H12B	109.0
C1—N1—H1A	118.9	C11—C12—H12B	109.0
C13—N1—H1A	118.9	H12A—C12—H12B	107.8
C21—N2—C14	108.87 (13)	C8—C13—N1	120.85 (13)
C21—N2—C22	124.59 (13)	C8—C13—C12	124.32 (14)
C14—N2—C22	126.53 (14)	N1—C13—C12	114.83 (12)
N1—C1—C6	120.86 (13)	C15—C14—N2	109.18 (14)
N1—C1—C2	115.80 (12)	C15—C14—C7	127.50 (13)
C6—C1—C2	123.32 (13)	N2—C14—C7	123.13 (13)
C1—C2—C3	112.90 (12)	C14—C15—C16	107.67 (13)
C1—C2—H2A	109.0	C14—C15—H15A	126.2
C3—C2—H2A	109.0	C16—C15—H15A	126.2
C1—C2—H2B	109.0	C17—C16—C21	118.88 (16)
C3—C2—H2B	109.0	C17—C16—C15	134.63 (16)
H2A—C2—H2B	107.8	C21—C16—C15	106.46 (14)
C25—C3—C2	108.61 (12)	C18—C17—C16	119.00 (17)
C25—C3—C4	110.33 (14)	C18—C17—H17A	120.5
C2—C3—C4	107.95 (11)	C16—C17—H17A	120.5
C25—C3—C26	109.69 (13)	C17—C18—C19	121.22 (17)
C2—C3—C26	110.44 (14)	C17—C18—H18A	119.4
C4—C3—C26	109.81 (13)	C19—C18—H18A	119.4
C5—C4—C3	113.54 (13)	C20—C19—C18	121.57 (17)
C5—C4—H4A	108.9	C20—C19—H19A	119.2
C3—C4—H4A	108.9	C18—C19—H19A	119.2
C5—C4—H4B	108.9	C19—C20—C21	117.24 (17)
C3—C4—H4B	108.9	C19—C20—H20A	121.4
H4A—C4—H4B	107.7	C21—C20—H20A	121.4
O1—C5—C6	120.36 (14)	N2—C21—C20	130.07 (15)
O1—C5—C4	120.34 (13)	N2—C21—C16	107.83 (13)
C6—C5—C4	119.25 (12)	C20—C21—C16	122.09 (16)
C1—C6—C5	119.64 (14)	N2—C22—H22A	109.5
C1—C6—C7	122.36 (13)	N2—C22—H22B	109.5
C5—C6—C7	117.98 (12)	H22A—C22—H22B	109.5
C6—C7—C14	108.54 (11)	N2—C22—H22C	109.5
C6—C7—C8	110.18 (11)	H22A—C22—H22C	109.5
C14—C7—C8	112.29 (13)	H22B—C22—H22C	109.5
C6—C7—H7A	108.6	C11—C23—H23A	109.5
C14—C7—H7A	108.6	C11—C23—H23B	109.5
C8—C7—H7A	108.6	H23A—C23—H23B	109.5
C13—C8—C9	119.72 (13)	C11—C23—H23C	109.5
C13—C8—C7	122.47 (13)	H23A—C23—H23C	109.5
C9—C8—C7	117.79 (12)	H23B—C23—H23C	109.5
O2—C9—C8	121.55 (14)	C11—C24—H24A	109.5
O2—C9—C10	121.06 (14)	C11—C24—H24B	109.5
C8—C9—C10	117.38 (13)	H24A—C24—H24B	109.5
C9—C10—C11	113.58 (14)	C11—C24—H24D	109.5
C9—C10—H10A	108.8	H24A—C24—H24D	109.5
C11—C10—H10A	108.8	H24B—C24—H24D	109.5
C9—C10—H10B	108.8	C3—C25—H25A	109.5
C11—C10—H10B	108.8	C3—C25—H25D	109.5
H10A—C10—H10B	107.7	H25A—C25—H25D	109.5
C24—C11—C23	109.14 (13)	C3—C25—H25B	109.5
C24—C11—C12	110.98 (14)	H25A—C25—H25B	109.5
C23—C11—C12	108.56 (12)	H25D—C25—H25B	109.5
C24—C11—C10	110.00 (13)	C3—C26—H26D	109.5
C23—C11—C10	110.47 (14)	C3—C26—H26A	109.5
C12—C11—C10	107.68 (13)	H26D—C26—H26A	109.5
C13—C12—C11	112.83 (12)	C3—C26—H26B	109.5
C13—C12—H12A	109.0	H26D—C26—H26B	109.5
C11—C12—H12A	109.0	H26A—C26—H26B	109.5
C13—N1—C1—C6	−4.8 (2)	C23—C11—C12—C13	168.26 (16)
C13—N1—C1—C2	173.19 (14)	C10—C11—C12—C13	48.64 (19)
N1—C1—C2—C3	156.80 (14)	C9—C8—C13—N1	−177.92 (14)
C6—C1—C2—C3	−25.2 (2)	C7—C8—C13—N1	0.6 (2)
C1—C2—C3—C25	169.70 (14)	C9—C8—C13—C12	2.1 (2)
C1—C2—C3—C4	50.08 (18)	C7—C8—C13—C12	−179.34 (15)
C1—C2—C3—C26	−69.98 (17)	C1—N1—C13—C8	7.2 (2)
C25—C3—C4—C5	−170.93 (13)	C1—N1—C13—C12	−172.86 (15)
C2—C3—C4—C5	−52.40 (18)	C11—C12—C13—C8	−24.4 (2)
C26—C3—C4—C5	68.06 (15)	C11—C12—C13—N1	155.59 (15)
C3—C4—C5—O1	−153.53 (14)	C21—N2—C14—C15	0.16 (19)
C3—C4—C5—C6	29.08 (19)	C22—N2—C14—C15	−178.97 (16)
N1—C1—C6—C5	176.66 (14)	C21—N2—C14—C7	175.40 (14)
C2—C1—C6—C5	−1.2 (2)	C22—N2—C14—C7	−3.7 (3)
N1—C1—C6—C7	−5.2 (2)	C6—C7—C14—C15	54.4 (2)
C2—C1—C6—C7	176.95 (14)	C8—C7—C14—C15	−67.67 (19)
O1—C5—C6—C1	−178.11 (14)	C6—C7—C14—N2	−119.94 (15)
C4—C5—C6—C1	−0.7 (2)	C8—C7—C14—N2	118.01 (15)
O1—C5—C6—C7	3.6 (2)	N2—C14—C15—C16	−0.04 (19)
C4—C5—C6—C7	−178.96 (13)	C7—C14—C15—C16	−175.01 (14)
C1—C6—C7—C14	−112.01 (15)	C14—C15—C16—C17	177.88 (18)
C5—C6—C7—C14	66.18 (16)	C14—C15—C16—C21	−0.09 (18)
C1—C6—C7—C8	11.32 (19)	C21—C16—C17—C18	−0.6 (3)
C5—C6—C7—C8	−170.49 (12)	C15—C16—C17—C18	−178.36 (19)
C6—C7—C8—C13	−9.1 (2)	C16—C17—C18—C19	0.1 (3)
C14—C7—C8—C13	112.07 (16)	C17—C18—C19—C20	0.1 (3)
C6—C7—C8—C9	169.54 (13)	C18—C19—C20—C21	0.1 (3)
C14—C7—C8—C9	−69.34 (16)	C14—N2—C21—C20	−179.10 (17)
C13—C8—C9—O2	173.83 (16)	C22—N2—C21—C20	0.1 (3)
C7—C8—C9—O2	−4.8 (2)	C14—N2—C21—C16	−0.22 (18)
C13—C8—C9—C10	−7.5 (2)	C22—N2—C21—C16	178.94 (16)
C7—C8—C9—C10	173.86 (14)	C19—C20—C21—N2	178.18 (18)
O2—C9—C10—C11	−145.85 (15)	C19—C20—C21—C16	−0.6 (3)
C8—C9—C10—C11	35.5 (2)	C17—C16—C21—N2	−178.16 (15)
C9—C10—C11—C24	66.05 (16)	C15—C16—C21—N2	0.19 (18)
C9—C10—C11—C23	−173.41 (13)	C17—C16—C21—C20	0.8 (3)
C9—C10—C11—C12	−55.01 (18)	C15—C16—C21—C20	179.18 (16)
C24—C11—C12—C13	−71.80 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22C···O2	0.98	2.54	3.314 (2)	136
N1—H1A···O1i	0.88	1.87	2.7437 (15)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C22—H22C⋯O2	0.98	2.54	3.314 (2)	136
N1—H1A⋯O1i	0.88	1.87	2.7437 (15)	170

Symmetry code: (i) .