3,3-Dimethyl-1,2,3,4-tetra-hydro-cyclo-penta-[b]indole-1,2-dione (bruceolline E).

The title compound, C(13)H(11)NO(2), crystallizes with two mol-ecules in the asymmetric unit. The crystal packing is stabilized by N-H⋯O hydrogen bonds, which link the mol-ecules into chains along [10[Formula: see text]], and weak C-H⋯O inter-actions.

Related literature

For the first isolation of bruceolline E as yellow needles, see: Ouyang et al. (1994 ▶). For the first total synthesis of n class="Chemical">bruceolline E in three steps from the known ethyl indole-1-carboxyl­ate, see: Jordan et al. (2011 ▶). For examples of similar tandem acyl­ation/Naza­rov cyclization with pyrroles, see: Song et al. (2006 ▶). For examples of Naza­rov cyclizations with indoles, see: Bergman & Venemalm (1992 ▶); Cheng & Cheung (1996 ▶); Ishikura et al. (2000 ▶); Miki et al. (2001 ▶); Churruca et al. (2010 ▶). For examples of α-diketone oxidations using selenium dioxide, see: Gribble et al. (1988 ▶); Xu et al. (2002 ▶); Belsey et al. (2006 ▶). For related cyclo­penta­[b]indolone alkaloids and their ana­logues, see: Cheng et al. (1991 ▶); Garcia-Pichel & Castenholz (1991 ▶); Garcia-Pichel et al. (1992 ▶); Proteau et al. (1993 ▶); Ekebergh et al. (2011 ▶); Kobayashi et al. (1994 ▶); Jacquemard et al. (2004 ▶); Ploutno & Carmeli (2001 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C13H11NO2

M = 213.23

Triclinic,

a = 9.1091 (7) Å

b = 11.5337 (8) Å

c = 11.8745 (9) Å

α = 63.230 (7)°

β = 80.596 (6)°

γ = 79.970 (6)°

V = 1091.69 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 170 K

0.28 × 0.25 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.976, T max = 0.979

10062 measured reflections

5644 independent reflections

4698 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.157

S = 1.05

5644 reflections

299 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis n class="Disease">RED (Oxford Diffraction, 2010 ▶); 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812000517/qm2048sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000517/qm2048Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812000517/qm2048Isup3.cml

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

C13H11NO2	Z = 4
Mr = 213.23	F(000) = 448
Triclinic, P1	Dx = 1.297 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.1091 (7) Å	Cell parameters from 5810 reflections
b = 11.5337 (8) Å	θ = 3.3–32.3°
c = 11.8745 (9) Å	µ = 0.09 mm−1
α = 63.230 (7)°	T = 170 K
β = 80.596 (6)°	Block, yellow
γ = 79.970 (6)°	0.28 × 0.25 × 0.24 mm
V = 1091.69 (14) Å3

Oxford Diffraction Xcalibur Eos Gemini diffractometer	5644 independent reflections
Radiation source: Enhance (Mo) X-ray Source	4698 reflections with I > 2σ(I)
graphite	Rint = 0.012
Detector resolution: 16.1500 pixels mm-1	θmax = 28.7°, θmin = 3.3°
ω scans	h = −12→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −15→15
Tmin = 0.976, Tmax = 0.979	l = −15→16
10062 measured reflections

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0864P)2 + 0.2278P] where P = (Fo2 + 2Fc2)/3
5644 reflections	(Δ/σ)max < 0.001
299 parameters	Δρmax = 0.36 e Å−3
2 restraints	Δρmin = −0.20 e Å−3

Experimental. 1H NMR (600 MHz, DMSO-d6) δ 12.9 (bs, 1H), 7.85 7.84 (d, J = 8.0 Hz, 1H), 7.62 7.61 (d, J = 8.1 Hz, 1H), 7.42 7.39 (t, J = 7.4 Hz, 1H), 7.34–7.31 (t, J = 7.7 Hz, 1H), 1.44 (s, 6H). 13C NMR (150 MHz, DMSO-d6) δ 206.6, 175.2, 171.0, 140.0, 125.4, 123.4, 121.5, 121.1, 121.0, 113.6, 41.6, 22.9; IR ν(KBr) 3418, 1750, 1665, 1469, 1453, 1210, 1152, 1094, 1013; UV λmax (95% MeOH) 256, 264, 272, 342 nm. Anal. Calcd for C13H11NO2: C, 73.22; H, 5.20; N 6.57. Found: C, 72.48; H, 5.30; N 6.40.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.75420 (16)	0.86467 (16)	0.18664 (11)	0.0673 (4)
O2	1.05510 (14)	0.75658 (14)	0.25613 (11)	0.0591 (3)
N1	0.76832 (12)	0.67293 (11)	0.63752 (10)	0.0329 (2)
H1NA	0.6811 (16)	0.6811 (16)	0.6806 (15)	0.039*
C1	0.67431 (15)	0.78837 (13)	0.41344 (12)	0.0330 (3)
C2	0.78552 (17)	0.80931 (15)	0.29437 (13)	0.0413 (3)
C3	0.94630 (16)	0.75106 (15)	0.33304 (13)	0.0398 (3)
C4	0.93046 (14)	0.69760 (13)	0.46734 (12)	0.0330 (3)
C5	1.01358 (15)	0.62976 (14)	0.57632 (13)	0.0358 (3)
C6	1.16300 (17)	0.58148 (19)	0.59556 (18)	0.0522 (4)
H6A	1.2361	0.5907	0.5260	0.063*
C7	1.2022 (2)	0.5200 (2)	0.7181 (2)	0.0653 (5)
H7A	1.3038	0.4862	0.7326	0.078*
C8	1.0970 (2)	0.5060 (2)	0.82122 (19)	0.0618 (5)
H8A	1.1280	0.4626	0.9044	0.074*
C9	0.94890 (19)	0.55398 (18)	0.80488 (15)	0.0496 (4)
H9A	0.8771	0.5453	0.8751	0.060*
C10	0.90872 (15)	0.61552 (14)	0.68187 (13)	0.0351 (3)
C11	0.78265 (14)	0.71996 (12)	0.51124 (11)	0.0289 (3)
C12	0.6013 (2)	0.92013 (15)	0.40795 (16)	0.0497 (4)
H12D	0.5338	0.9061	0.4851	0.074*
H12E	0.5442	0.9664	0.3338	0.074*
H12F	0.6791	0.9724	0.4014	0.074*
C13	0.55503 (18)	0.70394 (18)	0.42566 (17)	0.0495 (4)
H13D	0.4878	0.6899	0.5029	0.074*
H13E	0.6036	0.6194	0.4300	0.074*
H13F	0.4972	0.7484	0.3519	0.074*
N1A	0.10484 (12)	0.81468 (12)	1.00094 (10)	0.0343 (3)
H1NB	0.0732 (19)	0.8074 (16)	1.0812 (13)	0.041*
O1A	0.61629 (13)	0.64860 (15)	0.94255 (14)	0.0651 (4)
O2A	0.46978 (13)	0.73188 (12)	0.71755 (11)	0.0529 (3)
C1A	0.38431 (14)	0.72921 (13)	1.03441 (13)	0.0336 (3)
C2A	0.48880 (15)	0.69922 (14)	0.93239 (15)	0.0390 (3)
C3A	0.40683 (16)	0.74091 (13)	0.81363 (13)	0.0370 (3)
C4A	0.25841 (14)	0.78537 (13)	0.84578 (12)	0.0320 (3)
C5A	0.11410 (15)	0.83713 (13)	0.79856 (12)	0.0333 (3)
C6A	0.05507 (19)	0.87076 (16)	0.68526 (14)	0.0452 (3)
H6AA	0.1159	0.8600	0.6169	0.054*
C7A	−0.0938 (2)	0.92010 (18)	0.67500 (16)	0.0538 (4)
H7AA	−0.1353	0.9443	0.5980	0.065*
C8A	−0.18450 (19)	0.93526 (19)	0.77470 (18)	0.0568 (4)
H8AA	−0.2867	0.9692	0.7644	0.068*
C9A	−0.12946 (17)	0.90208 (18)	0.88854 (16)	0.0490 (4)
H9AA	−0.1916	0.9120	0.9568	0.059*
C10A	0.02018 (15)	0.85378 (13)	0.89824 (12)	0.0345 (3)
C11A	0.24447 (14)	0.77534 (12)	0.96840 (12)	0.0292 (3)
C12A	0.37519 (19)	0.60627 (17)	1.15941 (16)	0.0512 (4)
H12A	0.3434	0.5371	1.1456	0.077*
H12B	0.3025	0.6255	1.2211	0.077*
H12C	0.4738	0.5772	1.1919	0.077*
C13A	0.43957 (19)	0.83897 (17)	1.04967 (18)	0.0518 (4)
H13A	0.3713	0.8599	1.1125	0.078*
H13B	0.4424	0.9168	0.9681	0.078*
H13C	0.5403	0.8104	1.0781	0.078*

	U11	U22	U33	U12	U13	U23
O1	0.0641 (8)	0.0963 (10)	0.0291 (6)	0.0029 (7)	−0.0074 (5)	−0.0196 (6)
O2	0.0437 (6)	0.0938 (9)	0.0361 (6)	−0.0042 (6)	0.0117 (5)	−0.0315 (6)
N1	0.0271 (5)	0.0433 (6)	0.0241 (5)	−0.0003 (4)	0.0009 (4)	−0.0134 (4)
C1	0.0307 (6)	0.0383 (6)	0.0268 (6)	0.0014 (5)	−0.0042 (5)	−0.0127 (5)
C2	0.0429 (8)	0.0511 (8)	0.0273 (6)	−0.0021 (6)	−0.0012 (5)	−0.0165 (6)
C3	0.0350 (7)	0.0536 (8)	0.0310 (7)	−0.0033 (6)	0.0050 (5)	−0.0217 (6)
C4	0.0268 (6)	0.0428 (7)	0.0290 (6)	−0.0010 (5)	0.0014 (5)	−0.0175 (5)
C5	0.0284 (6)	0.0448 (7)	0.0356 (7)	0.0001 (5)	−0.0040 (5)	−0.0200 (6)
C6	0.0291 (7)	0.0757 (11)	0.0557 (10)	0.0045 (7)	−0.0059 (6)	−0.0351 (9)
C7	0.0378 (8)	0.0923 (14)	0.0728 (13)	0.0151 (9)	−0.0260 (9)	−0.0432 (11)
C8	0.0568 (11)	0.0806 (13)	0.0488 (10)	0.0086 (9)	−0.0269 (8)	−0.0273 (9)
C9	0.0471 (8)	0.0654 (10)	0.0334 (7)	0.0002 (7)	−0.0100 (6)	−0.0190 (7)
C10	0.0308 (6)	0.0429 (7)	0.0306 (6)	−0.0012 (5)	−0.0042 (5)	−0.0157 (5)
C11	0.0272 (6)	0.0335 (6)	0.0242 (6)	−0.0014 (4)	−0.0002 (4)	−0.0124 (5)
C12	0.0527 (9)	0.0409 (8)	0.0455 (8)	0.0076 (7)	−0.0038 (7)	−0.0149 (7)
C13	0.0394 (8)	0.0611 (9)	0.0523 (9)	−0.0075 (7)	−0.0085 (7)	−0.0263 (8)
N1A	0.0278 (5)	0.0469 (6)	0.0250 (5)	0.0028 (4)	−0.0006 (4)	−0.0159 (5)
O1A	0.0302 (6)	0.0908 (10)	0.0778 (9)	0.0113 (6)	−0.0046 (6)	−0.0463 (8)
O2A	0.0440 (6)	0.0689 (7)	0.0422 (6)	0.0004 (5)	0.0130 (5)	−0.0290 (6)
C1A	0.0280 (6)	0.0371 (6)	0.0338 (6)	0.0001 (5)	−0.0046 (5)	−0.0145 (5)
C2A	0.0272 (6)	0.0417 (7)	0.0461 (8)	−0.0024 (5)	0.0023 (5)	−0.0199 (6)
C3A	0.0342 (7)	0.0394 (7)	0.0345 (7)	−0.0039 (5)	0.0063 (5)	−0.0169 (5)
C4A	0.0311 (6)	0.0372 (6)	0.0257 (6)	−0.0032 (5)	0.0011 (5)	−0.0135 (5)
C5A	0.0327 (6)	0.0379 (6)	0.0271 (6)	−0.0041 (5)	−0.0013 (5)	−0.0126 (5)
C6A	0.0510 (9)	0.0542 (8)	0.0301 (7)	−0.0077 (7)	−0.0054 (6)	−0.0170 (6)
C7A	0.0543 (10)	0.0644 (10)	0.0390 (8)	−0.0065 (8)	−0.0201 (7)	−0.0142 (7)
C8A	0.0380 (8)	0.0717 (11)	0.0517 (10)	0.0019 (7)	−0.0157 (7)	−0.0179 (8)
C9A	0.0313 (7)	0.0662 (10)	0.0415 (8)	0.0043 (7)	−0.0037 (6)	−0.0199 (7)
C10A	0.0309 (6)	0.0406 (7)	0.0273 (6)	−0.0015 (5)	−0.0031 (5)	−0.0115 (5)
C11A	0.0266 (6)	0.0316 (6)	0.0261 (6)	−0.0010 (4)	0.0000 (4)	−0.0112 (5)
C12A	0.0402 (8)	0.0522 (9)	0.0417 (8)	0.0038 (6)	−0.0067 (6)	−0.0054 (7)
C13A	0.0453 (9)	0.0570 (9)	0.0638 (11)	−0.0044 (7)	−0.0134 (8)	−0.0336 (8)

O1—C2	1.2023 (18)	N1A—C11A	1.3301 (16)
O2—C3	1.2224 (17)	N1A—C10A	1.4057 (17)
N1—C11	1.3371 (16)	N1A—H1NB	0.919 (14)
N1—C10	1.4009 (17)	O1A—C2A	1.2042 (17)
N1—H1NA	0.887 (14)	O2A—C3A	1.2304 (17)
C1—C11	1.4910 (17)	C1A—C11A	1.4949 (17)
C1—C12	1.5260 (19)	C1A—C12A	1.525 (2)
C1—C13	1.530 (2)	C1A—C13A	1.532 (2)
C1—C2	1.5470 (19)	C1A—C2A	1.5424 (19)
C2—C3	1.551 (2)	C2A—C3A	1.545 (2)
C3—C4	1.4192 (19)	C3A—C4A	1.4151 (18)
C4—C11	1.3863 (17)	C4A—C11A	1.3937 (17)
C4—C5	1.4359 (19)	C4A—C5A	1.4370 (18)
C5—C6	1.3920 (19)	C5A—C6A	1.3939 (19)
C5—C10	1.4100 (19)	C5A—C10A	1.4095 (18)
C6—C7	1.379 (3)	C6A—C7A	1.378 (2)
C6—H6A	0.9500	C6A—H6AA	0.9500
C7—C8	1.392 (3)	C7A—C8A	1.390 (3)
C7—H7A	0.9500	C7A—H7AA	0.9500
C8—C9	1.376 (2)	C8A—C9A	1.383 (2)
C8—H8A	0.9500	C8A—H8AA	0.9500
C9—C10	1.386 (2)	C9A—C10A	1.3822 (19)
C9—H9A	0.9500	C9A—H9AA	0.9500
C12—H12D	0.9800	C12A—H12A	0.9800
C12—H12E	0.9800	C12A—H12B	0.9800
C12—H12F	0.9800	C12A—H12C	0.9800
C13—H13D	0.9800	C13A—H13A	0.9800
C13—H13E	0.9800	C13A—H13B	0.9800
C13—H13F	0.9800	C13A—H13C	0.9800
C11—N1—C10	108.76 (11)	C11A—N1A—C10A	108.31 (11)
C11—N1—H1NA	121.8 (11)	C11A—N1A—H1NB	122.5 (11)
C10—N1—H1NA	129.4 (11)	C10A—N1A—H1NB	129.0 (11)
C11—C1—C12	113.21 (12)	C11A—C1A—C12A	114.55 (12)
C11—C1—C13	113.17 (12)	C11A—C1A—C13A	111.77 (11)
C12—C1—C13	110.52 (13)	C12A—C1A—C13A	111.60 (14)
C11—C1—C2	98.41 (10)	C11A—C1A—C2A	97.98 (10)
C12—C1—C2	109.97 (12)	C12A—C1A—C2A	110.59 (12)
C13—C1—C2	110.99 (12)	C13A—C1A—C2A	109.51 (12)
O1—C2—C1	125.61 (14)	O1A—C2A—C1A	125.67 (14)
O1—C2—C3	124.13 (14)	O1A—C2A—C3A	123.63 (14)
C1—C2—C3	110.25 (11)	C1A—C2A—C3A	110.69 (11)
O2—C3—C4	132.30 (14)	O2A—C3A—C4A	132.76 (14)
O2—C3—C2	123.08 (13)	O2A—C3A—C2A	122.40 (13)
C4—C3—C2	104.62 (11)	C4A—C3A—C2A	104.84 (11)
C11—C4—C3	110.28 (12)	C11A—C4A—C3A	109.89 (12)
C11—C4—C5	107.02 (11)	C11A—C4A—C5A	107.00 (11)
C3—C4—C5	142.68 (12)	C3A—C4A—C5A	143.11 (13)
C6—C5—C10	119.17 (14)	C6A—C5A—C10A	119.22 (13)
C6—C5—C4	135.02 (13)	C6A—C5A—C4A	135.42 (13)
C10—C5—C4	105.80 (11)	C10A—C5A—C4A	105.36 (11)
C7—C6—C5	118.31 (16)	C7A—C6A—C5A	118.32 (15)
C7—C6—H6A	120.8	C7A—C6A—H6AA	120.8
C5—C6—H6A	120.8	C5A—C6A—H6AA	120.8
C6—C7—C8	121.72 (16)	C6A—C7A—C8A	121.50 (14)
C6—C7—H7A	119.1	C6A—C7A—H7AA	119.3
C8—C7—H7A	119.1	C8A—C7A—H7AA	119.3
C9—C8—C7	121.20 (16)	C9A—C8A—C7A	121.55 (15)
C9—C8—H8A	119.4	C9A—C8A—H8AA	119.2
C7—C8—H8A	119.4	C7A—C8A—H8AA	119.2
C8—C9—C10	117.32 (16)	C10A—C9A—C8A	116.88 (15)
C8—C9—H9A	121.3	C10A—C9A—H9AA	121.6
C10—C9—H9A	121.3	C8A—C9A—H9AA	121.6
C9—C10—N1	129.67 (13)	C9A—C10A—N1A	128.81 (13)
C9—C10—C5	122.27 (13)	C9A—C10A—C5A	122.53 (13)
N1—C10—C5	108.06 (11)	N1A—C10A—C5A	108.66 (11)
N1—C11—C4	110.35 (11)	N1A—C11A—C4A	110.66 (11)
N1—C11—C1	133.24 (11)	N1A—C11A—C1A	132.96 (12)
C4—C11—C1	116.41 (11)	C4A—C11A—C1A	116.33 (11)
C1—C12—H12D	109.5	C1A—C12A—H12A	109.5
C1—C12—H12E	109.5	C1A—C12A—H12B	109.5
H12D—C12—H12E	109.5	H12A—C12A—H12B	109.5
C1—C12—H12F	109.5	C1A—C12A—H12C	109.5
H12D—C12—H12F	109.5	H12A—C12A—H12C	109.5
H12E—C12—H12F	109.5	H12B—C12A—H12C	109.5
C1—C13—H13D	109.5	C1A—C13A—H13A	109.5
C1—C13—H13E	109.5	C1A—C13A—H13B	109.5
H13D—C13—H13E	109.5	H13A—C13A—H13B	109.5
C1—C13—H13F	109.5	C1A—C13A—H13C	109.5
H13D—C13—H13F	109.5	H13A—C13A—H13C	109.5
H13E—C13—H13F	109.5	H13B—C13A—H13C	109.5
C11—C1—C2—O1	−178.28 (17)	C11A—C1A—C2A—O1A	−174.04 (15)
C12—C1—C2—O1	−59.7 (2)	C12A—C1A—C2A—O1A	−54.0 (2)
C13—C1—C2—O1	62.9 (2)	C13A—C1A—C2A—O1A	69.41 (19)
C11—C1—C2—C3	0.43 (15)	C11A—C1A—C2A—C3A	4.93 (13)
C12—C1—C2—C3	118.96 (14)	C12A—C1A—C2A—C3A	124.99 (13)
C13—C1—C2—C3	−118.44 (13)	C13A—C1A—C2A—C3A	−111.62 (13)
O1—C2—C3—O2	−0.2 (3)	O1A—C2A—C3A—O2A	−4.3 (2)
C1—C2—C3—O2	−178.95 (15)	C1A—C2A—C3A—O2A	176.71 (13)
O1—C2—C3—C4	179.30 (17)	O1A—C2A—C3A—C4A	175.40 (15)
C1—C2—C3—C4	0.57 (16)	C1A—C2A—C3A—C4A	−3.60 (15)
O2—C3—C4—C11	178.02 (17)	O2A—C3A—C4A—C11A	−179.98 (16)
C2—C3—C4—C11	−1.44 (16)	C2A—C3A—C4A—C11A	0.37 (15)
O2—C3—C4—C5	−0.2 (3)	O2A—C3A—C4A—C5A	0.6 (3)
C2—C3—C4—C5	−179.69 (18)	C2A—C3A—C4A—C5A	−179.08 (17)
C11—C4—C5—C6	−179.60 (17)	C11A—C4A—C5A—C6A	179.17 (16)
C3—C4—C5—C6	−1.3 (3)	C3A—C4A—C5A—C6A	−1.4 (3)
C11—C4—C5—C10	−0.31 (15)	C11A—C4A—C5A—C10A	−0.72 (15)
C3—C4—C5—C10	177.97 (19)	C3A—C4A—C5A—C10A	178.74 (17)
C10—C5—C6—C7	0.7 (3)	C10A—C5A—C6A—C7A	0.4 (2)
C4—C5—C6—C7	179.91 (18)	C4A—C5A—C6A—C7A	−179.47 (16)
C5—C6—C7—C8	−0.3 (3)	C5A—C6A—C7A—C8A	−0.6 (3)
C6—C7—C8—C9	−0.4 (3)	C6A—C7A—C8A—C9A	0.3 (3)
C7—C8—C9—C10	0.6 (3)	C7A—C8A—C9A—C10A	0.3 (3)
C8—C9—C10—N1	−179.92 (16)	C8A—C9A—C10A—N1A	178.99 (15)
C8—C9—C10—C5	−0.2 (3)	C8A—C9A—C10A—C5A	−0.6 (3)
C11—N1—C10—C9	−179.70 (16)	C11A—N1A—C10A—C9A	−179.67 (15)
C11—N1—C10—C5	0.51 (16)	C11A—N1A—C10A—C5A	−0.06 (16)
C6—C5—C10—C9	−0.5 (2)	C6A—C5A—C10A—C9A	0.2 (2)
C4—C5—C10—C9	−179.92 (15)	C4A—C5A—C10A—C9A	−179.88 (14)
C6—C5—C10—N1	179.31 (14)	C6A—C5A—C10A—N1A	−179.42 (13)
C4—C5—C10—N1	−0.11 (15)	C4A—C5A—C10A—N1A	0.48 (15)
C10—N1—C11—C4	−0.73 (15)	C10A—N1A—C11A—C4A	−0.41 (15)
C10—N1—C11—C1	179.04 (14)	C10A—N1A—C11A—C1A	176.95 (13)
C3—C4—C11—N1	−178.24 (12)	C3A—C4A—C11A—N1A	−178.94 (11)
C5—C4—C11—N1	0.65 (16)	C5A—C4A—C11A—N1A	0.72 (15)
C3—C4—C11—C1	1.95 (17)	C3A—C4A—C11A—C1A	3.22 (16)
C5—C4—C11—C1	−179.16 (11)	C5A—C4A—C11A—C1A	−177.13 (11)
C12—C1—C11—N1	62.8 (2)	C12A—C1A—C11A—N1A	60.7 (2)
C13—C1—C11—N1	−63.97 (19)	C13A—C1A—C11A—N1A	−67.49 (19)
C2—C1—C11—N1	178.83 (15)	C2A—C1A—C11A—N1A	177.73 (14)
C12—C1—C11—C4	−117.46 (14)	C12A—C1A—C11A—C4A	−122.05 (14)
C13—C1—C11—C4	115.79 (14)	C13A—C1A—C11A—C4A	109.76 (14)
C2—C1—C11—C4	−1.41 (15)	C2A—C1A—C11A—C4A	−5.02 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1NA···O2A	0.89 (1)	1.95 (1)	2.8025 (16)	161.(2)
N1A—H1NB···O2i	0.92 (1)	1.87 (1)	2.7686 (16)	164.(2)
C9A—H9AA···O1i	0.95	2.51	3.376 (2)	152.
C12A—H12B···O2i	0.98	2.57	3.430 (2)	146.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1NA⋯O2A	0.89 (1)	1.95 (1)	2.8025 (16)	161 (2)
N1A—H1NB⋯O2i	0.92 (1)	1.87 (1)	2.7686 (16)	164 (2)
C9A—H9AA⋯O1i	0.95	2.51	3.376 (2)	152
C12A—H12B⋯O2i	0.98	2.57	3.430 (2)	146

Symmetry code: (i) .