Bruceolline D: 3,3-dimethyl-1H,4H-cyclo-penta-[b]indol-2(3H)-one.

The title compound, C13H13NO, crystallizes with four independent mol-ecules in the asymmetric unit. The 12-membered penta-[b]indole rings are essentially planar, with maximum deviations ranging from 0.034 (4) to 0.036 (4) Å in the four unique mol-ecules. In the crystal, weak C-H⋯O inter-actions are observed, which link the mol-ecules into chains along [010].

Related literature

For the first isolation of bruceolline D, see: Ouyang et al. (1994 ▶). For a Fischer indole synthesis approach to bruceolline D, see: Dashkevich (1978 ▶). For the methyl­ation of 2-methyl­cyclo­pentane-1,3-dione, see: Agosta & Smith (1970 ▶). For the palladium-catalysed synthesis of related fused indole structures, see: Nazare et al. (2004 ▶). For the isolation of related bruceollines, see: Chen et al. (2011 ▶). For the total synthesis and crystal structure of bruceolline E, see: Jordan et al. (2011 ▶, 2012 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C13H13NO

M = 199.24

Orthorhombic,

a = 10.13410 (14) Å

b = 21.9219 (3) Å

c = 19.3747 (3) Å

V = 4304.27 (11) Å3

Z = 16

Cu Kα radiation

μ = 0.62 mm−1

T = 173 K

0.32 × 0.18 × 0.06 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.876, T max = 1.000

28235 measured reflections

7612 independent reflections

7097 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.174

S = 1.04

7612 reflections

549 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.69 e Å−3

Δρmin = −0.33 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813014955/sj5328sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014955/sj5328Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813014955/sj5328Isup3.cml

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

C13H13NO	Dx = 1.230 Mg m−3
Mr = 199.24	Cu Kα radiation, λ = 1.5418 Å
Orthorhombic, Pbc21	Cell parameters from 11183 reflections
a = 10.13410 (14) Å	θ = 3.0–72.4°
b = 21.9219 (3) Å	µ = 0.62 mm−1
c = 19.3747 (3) Å	T = 173 K
V = 4304.27 (11) Å3	Prism, colourless
Z = 16	0.32 × 0.18 × 0.06 mm
F(000) = 1696

Agilent Xcalibur (Eos, Gemini) diffractometer	7612 independent reflections
Radiation source: Enhance (Cu) X-ray Source	7097 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
Detector resolution: 16.0416 pixels mm-1	θmax = 72.6°, θmin = 4.0°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	k = −26→19
Tmin = 0.876, Tmax = 1.000	l = −20→23
28235 measured reflections

Refinement on F2	1 restraint
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.068	H-atom parameters constrained
wR(F2) = 0.174	w = 1/[σ2(Fo2) + (0.1346P)2 + 0.5786P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
7612 reflections	Δρmax = 0.69 e Å−3
549 parameters	Δρmin = −0.33 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1A	0.9027 (4)	0.55207 (13)	0.52430 (17)	0.0587 (9)
N1A	0.9928 (3)	0.72326 (13)	0.67458 (17)	0.0311 (7)
H1A	1.0014	0.7162	0.7191	0.037*
C1A	0.9695 (3)	0.68058 (15)	0.62468 (19)	0.0301 (7)
C2A	0.9463 (4)	0.61292 (16)	0.6263 (2)	0.0353 (8)
C3A	0.9229 (4)	0.60183 (16)	0.5480 (2)	0.0384 (8)
C4A	0.9289 (4)	0.66154 (16)	0.50654 (19)	0.0353 (8)
H4AA	0.9983	0.6600	0.4707	0.042*
H4AB	0.8430	0.6709	0.4846	0.042*
C5A	0.9618 (3)	0.70689 (15)	0.56179 (18)	0.0279 (6)
C6A	0.9823 (3)	0.77087 (15)	0.57072 (19)	0.0268 (7)
C7A	0.9849 (3)	0.82163 (16)	0.5269 (2)	0.0301 (7)
H7A	0.9746	0.8169	0.4785	0.036*
C8A	1.0027 (3)	0.87872 (16)	0.5556 (2)	0.0347 (8)
H8A	1.0037	0.9135	0.5264	0.042*
C9A	1.0194 (4)	0.88624 (17)	0.6267 (2)	0.0382 (9)
H9A	1.0310	0.9262	0.6447	0.046*
C10A	1.0195 (4)	0.83725 (16)	0.6713 (2)	0.0339 (8)
H10A	1.0321	0.8427	0.7195	0.041*
C11A	1.0003 (3)	0.77912 (15)	0.64301 (19)	0.0271 (7)
C12A	1.0664 (4)	0.57622 (19)	0.6513 (3)	0.0545 (11)
H12A	1.1450	0.5890	0.6255	0.082*
H12B	1.0507	0.5326	0.6436	0.082*
H12C	1.0802	0.5837	0.7006	0.082*
C13A	0.8226 (4)	0.59501 (19)	0.6668 (2)	0.0455 (9)
H13A	0.8369	0.6027	0.7160	0.068*
H13B	0.8041	0.5516	0.6596	0.068*
H13C	0.7474	0.6193	0.6506	0.068*
O1B	0.4157 (3)	0.15987 (11)	0.55334 (18)	0.0456 (7)
N1B	0.6744 (3)	0.34522 (12)	0.56110 (16)	0.0312 (6)
H1B	0.7609	0.3419	0.5635	0.037*
C1B	0.5864 (3)	0.29805 (14)	0.55585 (18)	0.0273 (6)
C2B	0.6016 (3)	0.23033 (14)	0.5527 (2)	0.0312 (7)
C3B	0.4528 (3)	0.21198 (15)	0.5510 (2)	0.0323 (7)
C4B	0.3632 (3)	0.26770 (14)	0.5476 (2)	0.0339 (7)
H4BA	0.3148	0.2695	0.5032	0.041*
H4BB	0.2993	0.2682	0.5862	0.041*
C5B	0.4611 (3)	0.31874 (15)	0.55362 (19)	0.0289 (7)
C6B	0.4668 (3)	0.38412 (14)	0.55765 (18)	0.0282 (7)
C7B	0.3743 (3)	0.43185 (16)	0.55652 (18)	0.0339 (7)
H7B	0.2825	0.4235	0.5541	0.041*
C8B	0.4203 (4)	0.49188 (15)	0.55907 (19)	0.0366 (8)
H8B	0.3590	0.5246	0.5583	0.044*
C9B	0.5547 (4)	0.50435 (16)	0.5627 (2)	0.0368 (8)
H9B	0.5828	0.5457	0.5641	0.044*
C10B	0.6479 (4)	0.45913 (15)	0.56428 (19)	0.0345 (7)
H10B	0.7394	0.4684	0.5669	0.041*
C11B	0.6032 (3)	0.39884 (14)	0.56189 (18)	0.0295 (7)
C12B	0.6717 (4)	0.20825 (18)	0.4870 (2)	0.0469 (10)
H12D	0.6260	0.2245	0.4464	0.070*
H12E	0.6705	0.1636	0.4855	0.070*
H12F	0.7632	0.2226	0.4872	0.070*
C13B	0.6669 (4)	0.20277 (16)	0.6170 (2)	0.0446 (9)
H13D	0.7598	0.2151	0.6187	0.067*
H13E	0.6613	0.1582	0.6148	0.067*
H13F	0.6214	0.2174	0.6584	0.067*
O1C	0.6041 (4)	0.69989 (13)	0.37896 (17)	0.0555 (8)
N1C	0.5290 (3)	0.52512 (13)	0.23148 (17)	0.0328 (7)
H1C	0.5229	0.5313	0.1867	0.039*
C1C	0.5509 (3)	0.56889 (15)	0.28084 (18)	0.0294 (7)
C2C	0.5704 (4)	0.63639 (16)	0.27780 (19)	0.0347 (7)
C3C	0.5900 (3)	0.64918 (16)	0.3560 (2)	0.0365 (8)
C4C	0.5840 (4)	0.59052 (16)	0.39915 (19)	0.0349 (7)
H4CA	0.6690	0.5825	0.4226	0.042*
H4CB	0.5126	0.5923	0.4339	0.042*
C5C	0.5558 (3)	0.54359 (15)	0.34498 (18)	0.0288 (6)
C6C	0.5340 (3)	0.47964 (14)	0.33686 (18)	0.0267 (7)
C7C	0.5275 (3)	0.42955 (16)	0.3818 (2)	0.0318 (7)
H7C	0.5378	0.4352	0.4301	0.038*
C8C	0.5058 (3)	0.37180 (16)	0.3550 (2)	0.0348 (8)
H8C	0.5002	0.3377	0.3850	0.042*
C9C	0.4921 (4)	0.36376 (16)	0.2839 (2)	0.0372 (9)
H9C	0.4776	0.3238	0.2666	0.045*
C10C	0.4987 (3)	0.41164 (16)	0.2377 (2)	0.0334 (8)
H10C	0.4904	0.4053	0.1894	0.040*
C11C	0.5181 (3)	0.46927 (15)	0.2650 (2)	0.0280 (7)
C12C	0.4486 (4)	0.67119 (17)	0.2516 (3)	0.0506 (11)
H12G	0.4339	0.6615	0.2028	0.076*
H12H	0.4632	0.7151	0.2568	0.076*
H12I	0.3711	0.6591	0.2786	0.076*
C13C	0.6936 (4)	0.6559 (2)	0.2375 (2)	0.0460 (9)
H13G	0.7707	0.6341	0.2555	0.069*
H13H	0.7068	0.6999	0.2428	0.069*
H13I	0.6819	0.6460	0.1886	0.069*
O1D	−0.0630 (3)	0.59408 (11)	0.35172 (17)	0.0451 (7)
N1D	0.1833 (3)	0.40513 (11)	0.35371 (16)	0.0299 (6)
H1D	0.2700	0.4070	0.3551	0.036*
C1D	0.0984 (3)	0.45404 (15)	0.35461 (18)	0.0282 (6)
C2D	0.1177 (3)	0.52123 (14)	0.35591 (19)	0.0307 (7)
C3D	−0.0296 (3)	0.54136 (15)	0.3543 (2)	0.0333 (8)
C4D	−0.1232 (3)	0.48702 (16)	0.3542 (2)	0.0375 (8)
H4DA	−0.1779	0.4860	0.3965	0.045*
H4DB	−0.1815	0.4874	0.3132	0.045*
C5D	−0.0288 (3)	0.43463 (15)	0.3519 (2)	0.0307 (7)
C6D	−0.0265 (3)	0.36943 (15)	0.3490 (2)	0.0315 (7)
C7D	−0.1231 (4)	0.32326 (17)	0.3459 (2)	0.0399 (8)
H7D	−0.2143	0.3331	0.3444	0.048*
C8D	−0.0809 (4)	0.26286 (17)	0.3451 (2)	0.0430 (9)
H8D	−0.1447	0.2311	0.3434	0.052*
C9D	0.0526 (4)	0.24775 (16)	0.3467 (2)	0.0394 (8)
H9D	0.0779	0.2060	0.3463	0.047*
C10D	0.1482 (4)	0.29203 (15)	0.34891 (19)	0.0372 (8)
H10D	0.2391	0.2815	0.3495	0.045*
C11D	0.1085 (3)	0.35272 (14)	0.35022 (18)	0.0304 (7)
C12D	0.1847 (4)	0.5439 (2)	0.4218 (2)	0.0487 (10)
H12J	0.1354	0.5294	0.4621	0.073*
H12K	0.1864	0.5886	0.4218	0.073*
H12L	0.2752	0.5283	0.4237	0.073*
C13D	0.1868 (4)	0.54571 (17)	0.2920 (2)	0.0469 (10)
H13J	0.2803	0.5344	0.2934	0.070*
H13K	0.1789	0.5902	0.2907	0.070*
H13L	0.1459	0.5283	0.2506	0.070*

	U11	U22	U33	U12	U13	U23
O1A	0.093 (3)	0.0354 (15)	0.0473 (17)	−0.0261 (15)	0.0177 (17)	−0.0125 (12)
N1A	0.0434 (16)	0.0309 (15)	0.0191 (15)	−0.0056 (11)	0.0003 (11)	−0.0026 (11)
C1A	0.0331 (16)	0.0282 (16)	0.0289 (18)	−0.0043 (12)	0.0039 (13)	−0.0030 (13)
C2A	0.0396 (18)	0.0309 (17)	0.036 (2)	−0.0089 (14)	0.0013 (15)	0.0004 (14)
C3A	0.0433 (19)	0.0360 (18)	0.0359 (19)	−0.0109 (14)	0.0103 (15)	−0.0050 (15)
C4A	0.0418 (18)	0.0346 (18)	0.0296 (18)	−0.0074 (14)	−0.0006 (15)	−0.0044 (14)
C5A	0.0297 (14)	0.0294 (15)	0.0246 (17)	−0.0031 (12)	0.0031 (12)	−0.0038 (13)
C6A	0.0249 (13)	0.0302 (17)	0.0253 (17)	−0.0019 (11)	0.0011 (12)	−0.0030 (13)
C7A	0.0284 (15)	0.0322 (17)	0.0298 (19)	−0.0015 (12)	−0.0036 (13)	0.0016 (14)
C8A	0.0301 (15)	0.0266 (16)	0.047 (3)	0.0029 (12)	−0.0020 (15)	0.0054 (17)
C9A	0.0363 (18)	0.0285 (17)	0.050 (3)	0.0012 (13)	0.0013 (16)	−0.0117 (17)
C10A	0.0384 (18)	0.0317 (18)	0.032 (2)	−0.0030 (13)	0.0054 (15)	−0.0081 (15)
C11A	0.0286 (15)	0.0296 (17)	0.0231 (19)	−0.0011 (12)	0.0020 (12)	−0.0041 (13)
C12A	0.048 (2)	0.037 (2)	0.079 (3)	−0.0004 (17)	−0.006 (2)	0.005 (2)
C13A	0.051 (2)	0.049 (2)	0.036 (2)	−0.0195 (17)	0.0049 (17)	0.0028 (16)
O1B	0.0417 (14)	0.0260 (12)	0.069 (2)	−0.0092 (10)	0.0051 (14)	−0.0036 (12)
N1B	0.0253 (12)	0.0252 (12)	0.0432 (17)	−0.0049 (9)	−0.0014 (12)	0.0024 (11)
C1B	0.0288 (14)	0.0213 (14)	0.0319 (17)	−0.0054 (11)	0.0013 (13)	−0.0010 (12)
C2B	0.0284 (15)	0.0244 (15)	0.041 (2)	−0.0005 (11)	0.0026 (14)	−0.0028 (13)
C3B	0.0289 (15)	0.0291 (16)	0.039 (2)	−0.0075 (12)	0.0052 (14)	−0.0022 (14)
C4B	0.0246 (14)	0.0309 (16)	0.046 (2)	−0.0035 (12)	0.0009 (14)	−0.0026 (14)
C5B	0.0296 (15)	0.0256 (15)	0.0316 (19)	−0.0002 (12)	−0.0010 (13)	0.0010 (13)
C6B	0.0378 (17)	0.0210 (15)	0.0259 (18)	−0.0045 (11)	−0.0021 (13)	0.0002 (12)
C7B	0.0355 (16)	0.0349 (17)	0.0312 (17)	0.0017 (13)	−0.0011 (14)	−0.0003 (14)
C8B	0.054 (2)	0.0264 (16)	0.0290 (18)	0.0120 (14)	−0.0023 (16)	0.0009 (14)
C9B	0.059 (2)	0.0238 (16)	0.0274 (18)	−0.0080 (14)	−0.0063 (16)	0.0031 (13)
C10B	0.0397 (17)	0.0307 (16)	0.0331 (18)	−0.0095 (13)	−0.0014 (14)	0.0028 (14)
C11B	0.0331 (15)	0.0270 (15)	0.0285 (17)	0.0001 (12)	−0.0003 (13)	0.0003 (13)
C12B	0.039 (2)	0.042 (2)	0.060 (3)	−0.0008 (15)	0.0147 (18)	−0.0147 (18)
C13B	0.041 (2)	0.0298 (18)	0.063 (3)	0.0036 (14)	−0.0026 (18)	0.0105 (17)
O1C	0.080 (2)	0.0346 (14)	0.0520 (18)	−0.0222 (14)	0.0161 (16)	−0.0098 (12)
N1C	0.0434 (16)	0.0320 (16)	0.0229 (16)	−0.0052 (11)	−0.0011 (12)	−0.0013 (12)
C1C	0.0256 (15)	0.0336 (16)	0.0290 (18)	−0.0027 (12)	0.0017 (13)	−0.0030 (13)
C2C	0.0385 (17)	0.0318 (17)	0.0339 (19)	−0.0077 (13)	0.0003 (14)	0.0007 (14)
C3C	0.0373 (17)	0.0343 (18)	0.038 (2)	−0.0114 (13)	0.0063 (15)	−0.0059 (15)
C4C	0.0399 (18)	0.0328 (17)	0.0320 (18)	−0.0050 (13)	0.0017 (15)	−0.0045 (14)
C5C	0.0238 (13)	0.0320 (15)	0.0305 (17)	−0.0016 (11)	0.0006 (13)	−0.0021 (13)
C6C	0.0230 (13)	0.0305 (16)	0.0264 (18)	0.0009 (11)	−0.0003 (12)	−0.0022 (13)
C7C	0.0309 (15)	0.0314 (17)	0.033 (2)	0.0024 (13)	−0.0005 (13)	0.0034 (14)
C8C	0.0300 (15)	0.0283 (17)	0.046 (2)	0.0033 (12)	0.0000 (15)	0.0055 (17)
C9C	0.0391 (18)	0.0226 (16)	0.050 (3)	0.0024 (12)	0.0020 (15)	−0.0048 (16)
C10C	0.0304 (16)	0.0330 (19)	0.037 (2)	0.0017 (12)	−0.0007 (14)	−0.0119 (16)
C11C	0.0239 (14)	0.0292 (17)	0.031 (2)	0.0025 (11)	−0.0002 (12)	−0.0015 (14)
C12C	0.052 (2)	0.0301 (19)	0.070 (3)	−0.0010 (16)	−0.009 (2)	0.0078 (18)
C13C	0.047 (2)	0.052 (2)	0.039 (2)	−0.0212 (17)	0.0042 (17)	0.0021 (17)
O1D	0.0455 (14)	0.0275 (12)	0.0624 (19)	0.0103 (10)	−0.0065 (14)	−0.0039 (12)
N1D	0.0255 (12)	0.0268 (13)	0.0375 (16)	0.0054 (10)	0.0005 (11)	0.0014 (11)
C1D	0.0270 (14)	0.0257 (15)	0.0318 (17)	0.0062 (12)	0.0000 (13)	0.0008 (13)
C2D	0.0287 (14)	0.0236 (14)	0.0397 (19)	0.0005 (11)	−0.0046 (14)	−0.0010 (13)
C3D	0.0384 (18)	0.0251 (15)	0.037 (2)	0.0061 (13)	−0.0032 (15)	−0.0051 (14)
C4D	0.0242 (14)	0.0321 (16)	0.056 (2)	0.0039 (13)	−0.0032 (15)	−0.0058 (16)
C5D	0.0315 (16)	0.0238 (15)	0.037 (2)	−0.0031 (12)	−0.0013 (14)	−0.0021 (14)
C6D	0.0381 (17)	0.0264 (16)	0.0302 (19)	0.0005 (12)	0.0028 (14)	0.0018 (14)
C7D	0.0367 (17)	0.0410 (19)	0.042 (2)	−0.0044 (15)	0.0063 (16)	−0.0023 (16)
C8D	0.061 (2)	0.0346 (18)	0.034 (2)	−0.0183 (16)	0.0113 (18)	−0.0035 (15)
C9D	0.069 (2)	0.0227 (16)	0.0268 (19)	0.0078 (15)	0.0089 (17)	0.0018 (14)
C10D	0.0519 (19)	0.0309 (16)	0.0287 (17)	0.0095 (14)	0.0089 (16)	0.0024 (14)
C11D	0.0378 (17)	0.0271 (15)	0.0263 (16)	0.0022 (12)	0.0028 (14)	0.0045 (13)
C12D	0.0408 (19)	0.046 (2)	0.059 (3)	0.0044 (16)	−0.0154 (18)	−0.0166 (18)
C13D	0.041 (2)	0.0347 (18)	0.064 (3)	−0.0014 (15)	0.0044 (18)	0.0107 (18)

O1A—C3A	1.201 (4)	O1C—C3C	1.206 (4)
N1A—H1A	0.8800	N1C—H1C	0.8800
N1A—C1A	1.366 (4)	N1C—C1C	1.373 (4)
N1A—C11A	1.371 (4)	N1C—C11C	1.390 (5)
C1A—C2A	1.502 (5)	C1C—C2C	1.494 (5)
C1A—C5A	1.350 (5)	C1C—C5C	1.362 (5)
C2A—C3A	1.554 (5)	C2C—C3C	1.554 (5)
C2A—C12A	1.537 (6)	C2C—C12C	1.537 (6)
C2A—C13A	1.531 (5)	C2C—C13C	1.533 (5)
C3A—C4A	1.537 (5)	C3C—C4C	1.534 (5)
C4A—H4AA	0.9900	C4C—H4CA	0.9900
C4A—H4AB	0.9900	C4C—H4CB	0.9900
C4A—C5A	1.498 (4)	C4C—C5C	1.497 (5)
C5A—C6A	1.429 (4)	C5C—C6C	1.428 (4)
C6A—C7A	1.400 (5)	C6C—C7C	1.403 (5)
C6A—C11A	1.424 (5)	C6C—C11C	1.420 (5)
C7A—H7A	0.9500	C7C—H7C	0.9500
C7A—C8A	1.381 (5)	C7C—C8C	1.386 (5)
C8A—H8A	0.9500	C8C—H8C	0.9500
C8A—C9A	1.398 (7)	C8C—C9C	1.395 (6)
C9A—H9A	0.9500	C9C—H9C	0.9500
C9A—C10A	1.378 (6)	C9C—C10C	1.381 (6)
C10A—H10A	0.9500	C10C—H10C	0.9500
C10A—C11A	1.401 (5)	C10C—C11C	1.383 (5)
C12A—H12A	0.9800	C12C—H12G	0.9800
C12A—H12B	0.9800	C12C—H12H	0.9800
C12A—H12C	0.9800	C12C—H12I	0.9800
C13A—H13A	0.9800	C13C—H13G	0.9800
C13A—H13B	0.9800	C13C—H13H	0.9800
C13A—H13C	0.9800	C13C—H13I	0.9800
O1B—C3B	1.204 (4)	O1D—C3D	1.205 (4)
N1B—H1B	0.8800	N1D—H1D	0.8800
N1B—C1B	1.370 (4)	N1D—C1D	1.375 (4)
N1B—C11B	1.379 (4)	N1D—C11D	1.378 (4)
C1B—C2B	1.494 (4)	C1D—C2D	1.486 (4)
C1B—C5B	1.349 (4)	C1D—C5D	1.359 (5)
C2B—C3B	1.561 (4)	C2D—C3D	1.558 (4)
C2B—C12B	1.536 (5)	C2D—C12D	1.529 (5)
C2B—C13B	1.534 (5)	C2D—C13D	1.521 (6)
C3B—C4B	1.523 (4)	C3D—C4D	1.522 (5)
C4B—H4BA	0.9900	C4D—H4DA	0.9900
C4B—H4BB	0.9900	C4D—H4DB	0.9900
C4B—C5B	1.500 (4)	C4D—C5D	1.495 (4)
C5B—C6B	1.437 (4)	C5D—C6D	1.431 (5)
C6B—C7B	1.405 (5)	C6D—C7D	1.409 (5)
C6B—C11B	1.422 (5)	C6D—C11D	1.417 (5)
C7B—H7B	0.9500	C7D—H7D	0.9500
C7B—C8B	1.397 (5)	C7D—C8D	1.391 (5)
C8B—H8B	0.9500	C8D—H8D	0.9500
C8B—C9B	1.391 (5)	C8D—C9D	1.393 (6)
C9B—H9B	0.9500	C9D—H9D	0.9500
C9B—C10B	1.370 (5)	C9D—C10D	1.372 (5)
C10B—H10B	0.9500	C10D—H10D	0.9500
C10B—C11B	1.398 (4)	C10D—C11D	1.390 (5)
C12B—H12D	0.9800	C12D—H12J	0.9800
C12B—H12E	0.9800	C12D—H12K	0.9800
C12B—H12F	0.9800	C12D—H12L	0.9800
C13B—H13D	0.9800	C13D—H13J	0.9800
C13B—H13E	0.9800	C13D—H13K	0.9800
C13B—H13F	0.9800	C13D—H13L	0.9800
C1A—N1A—H1A	126.1	C1C—N1C—H1C	126.2
C1A—N1A—C11A	107.8 (3)	C1C—N1C—C11C	107.7 (3)
C11A—N1A—H1A	126.1	C11C—N1C—H1C	126.2
N1A—C1A—C2A	133.5 (3)	N1C—C1C—C2C	133.3 (3)
C5A—C1A—N1A	110.9 (3)	C5C—C1C—N1C	110.9 (3)
C5A—C1A—C2A	115.5 (3)	C5C—C1C—C2C	115.8 (3)
C1A—C2A—C3A	99.1 (3)	C1C—C2C—C3C	99.0 (3)
C1A—C2A—C12A	113.6 (3)	C1C—C2C—C12C	113.5 (3)
C1A—C2A—C13A	113.1 (3)	C1C—C2C—C13C	113.8 (3)
C12A—C2A—C3A	110.3 (4)	C12C—C2C—C3C	109.6 (3)
C13A—C2A—C3A	109.6 (3)	C13C—C2C—C3C	110.0 (3)
C13A—C2A—C12A	110.7 (3)	C13C—C2C—C12C	110.4 (3)
O1A—C3A—C2A	122.7 (4)	O1C—C3C—C2C	122.7 (4)
O1A—C3A—C4A	125.5 (4)	O1C—C3C—C4C	125.2 (4)
C4A—C3A—C2A	111.7 (3)	C4C—C3C—C2C	112.0 (3)
C3A—C4A—H4AA	111.5	C3C—C4C—H4CA	111.4
C3A—C4A—H4AB	111.5	C3C—C4C—H4CB	111.4
H4AA—C4A—H4AB	109.3	H4CA—C4C—H4CB	109.3
C5A—C4A—C3A	101.6 (3)	C5C—C4C—C3C	101.6 (3)
C5A—C4A—H4AA	111.5	C5C—C4C—H4CA	111.4
C5A—C4A—H4AB	111.5	C5C—C4C—H4CB	111.4
C1A—C5A—C4A	112.0 (3)	C1C—C5C—C4C	111.5 (3)
C1A—C5A—C6A	107.6 (3)	C1C—C5C—C6C	107.1 (3)
C6A—C5A—C4A	140.4 (3)	C6C—C5C—C4C	141.4 (3)
C7A—C6A—C5A	135.2 (3)	C7C—C6C—C5C	135.0 (3)
C7A—C6A—C11A	119.6 (3)	C7C—C6C—C11C	118.5 (3)
C11A—C6A—C5A	105.2 (3)	C11C—C6C—C5C	106.4 (3)
C6A—C7A—H7A	120.7	C6C—C7C—H7C	120.3
C8A—C7A—C6A	118.6 (4)	C8C—C7C—C6C	119.3 (4)
C8A—C7A—H7A	120.7	C8C—C7C—H7C	120.3
C7A—C8A—H8A	119.4	C7C—C8C—H8C	120.0
C7A—C8A—C9A	121.3 (4)	C7C—C8C—C9C	120.1 (4)
C9A—C8A—H8A	119.4	C9C—C8C—H8C	120.0
C8A—C9A—H9A	119.1	C8C—C9C—H9C	118.7
C10A—C9A—C8A	121.7 (3)	C10C—C9C—C8C	122.6 (3)
C10A—C9A—H9A	119.1	C10C—C9C—H9C	118.7
C9A—C10A—H10A	121.2	C9C—C10C—H10C	121.5
C9A—C10A—C11A	117.6 (4)	C9C—C10C—C11C	117.0 (4)
C11A—C10A—H10A	121.2	C11C—C10C—H10C	121.5
N1A—C11A—C6A	108.6 (3)	N1C—C11C—C6C	107.9 (3)
N1A—C11A—C10A	130.2 (3)	C10C—C11C—N1C	129.6 (4)
C10A—C11A—C6A	121.2 (3)	C10C—C11C—C6C	122.5 (3)
C2A—C12A—H12A	109.5	C2C—C12C—H12G	109.5
C2A—C12A—H12B	109.5	C2C—C12C—H12H	109.5
C2A—C12A—H12C	109.5	C2C—C12C—H12I	109.5
H12A—C12A—H12B	109.5	H12G—C12C—H12H	109.5
H12A—C12A—H12C	109.5	H12G—C12C—H12I	109.5
H12B—C12A—H12C	109.5	H12H—C12C—H12I	109.5
C2A—C13A—H13A	109.5	C2C—C13C—H13G	109.5
C2A—C13A—H13B	109.5	C2C—C13C—H13H	109.5
C2A—C13A—H13C	109.5	C2C—C13C—H13I	109.5
H13A—C13A—H13B	109.5	H13G—C13C—H13H	109.5
H13A—C13A—H13C	109.5	H13G—C13C—H13I	109.5
H13B—C13A—H13C	109.5	H13H—C13C—H13I	109.5
C1B—N1B—H1B	126.2	C1D—N1D—H1D	126.1
C1B—N1B—C11B	107.7 (3)	C1D—N1D—C11D	107.9 (3)
C11B—N1B—H1B	126.2	C11D—N1D—H1D	126.1
N1B—C1B—C2B	133.3 (3)	N1D—C1D—C2D	133.7 (3)
C5B—C1B—N1B	111.2 (3)	C5D—C1D—N1D	110.4 (3)
C5B—C1B—C2B	115.5 (3)	C5D—C1D—C2D	115.8 (3)
C1B—C2B—C3B	99.0 (2)	C1D—C2D—C3D	98.9 (2)
C1B—C2B—C12B	113.2 (3)	C1D—C2D—C12D	113.3 (3)
C1B—C2B—C13B	113.8 (3)	C1D—C2D—C13D	113.4 (3)
C12B—C2B—C3B	110.4 (3)	C12D—C2D—C3D	110.5 (3)
C13B—C2B—C3B	109.4 (3)	C13D—C2D—C3D	109.0 (3)
C13B—C2B—C12B	110.4 (3)	C13D—C2D—C12D	111.2 (3)
O1B—C3B—C2B	123.1 (3)	O1D—C3D—C2D	122.8 (3)
O1B—C3B—C4B	125.2 (3)	O1D—C3D—C4D	125.2 (3)
C4B—C3B—C2B	111.7 (3)	C4D—C3D—C2D	112.0 (3)
C3B—C4B—H4BA	111.5	C3D—C4D—H4DA	111.4
C3B—C4B—H4BB	111.5	C3D—C4D—H4DB	111.4
H4BA—C4B—H4BB	109.3	H4DA—C4D—H4DB	109.3
C5B—C4B—C3B	101.6 (3)	C5D—C4D—C3D	101.7 (3)
C5B—C4B—H4BA	111.5	C5D—C4D—H4DA	111.4
C5B—C4B—H4BB	111.5	C5D—C4D—H4DB	111.4
C1B—C5B—C4B	112.0 (3)	C1D—C5D—C4D	111.4 (3)
C1B—C5B—C6B	107.2 (3)	C1D—C5D—C6D	107.4 (3)
C6B—C5B—C4B	140.8 (3)	C6D—C5D—C4D	141.2 (3)
C7B—C6B—C5B	135.7 (3)	C7D—C6D—C5D	135.1 (3)
C7B—C6B—C11B	118.7 (3)	C7D—C6D—C11D	119.1 (3)
C11B—C6B—C5B	105.6 (3)	C11D—C6D—C5D	105.9 (3)
C6B—C7B—H7B	120.7	C6D—C7D—H7D	121.0
C8B—C7B—C6B	118.6 (3)	C8D—C7D—C6D	118.1 (3)
C8B—C7B—H7B	120.7	C8D—C7D—H7D	121.0
C7B—C8B—H8B	119.5	C7D—C8D—H8D	119.2
C9B—C8B—C7B	120.9 (3)	C7D—C8D—C9D	121.6 (3)
C9B—C8B—H8B	119.5	C9D—C8D—H8D	119.2
C8B—C9B—H9B	118.9	C8D—C9D—H9D	119.4
C10B—C9B—C8B	122.3 (3)	C10D—C9D—C8D	121.2 (3)
C10B—C9B—H9B	118.9	C10D—C9D—H9D	119.4
C9B—C10B—H10B	121.3	C9D—C10D—H10D	120.9
C9B—C10B—C11B	117.4 (3)	C9D—C10D—C11D	118.2 (3)
C11B—C10B—H10B	121.3	C11D—C10D—H10D	120.9
N1B—C11B—C6B	108.3 (3)	N1D—C11D—C6D	108.4 (3)
N1B—C11B—C10B	129.5 (3)	N1D—C11D—C10D	129.8 (3)
C10B—C11B—C6B	122.1 (3)	C10D—C11D—C6D	121.8 (3)
C2B—C12B—H12D	109.5	C2D—C12D—H12J	109.5
C2B—C12B—H12E	109.5	C2D—C12D—H12K	109.5
C2B—C12B—H12F	109.5	C2D—C12D—H12L	109.5
H12D—C12B—H12E	109.5	H12J—C12D—H12K	109.5
H12D—C12B—H12F	109.5	H12J—C12D—H12L	109.5
H12E—C12B—H12F	109.5	H12K—C12D—H12L	109.5
C2B—C13B—H13D	109.5	C2D—C13D—H13J	109.5
C2B—C13B—H13E	109.5	C2D—C13D—H13K	109.5
C2B—C13B—H13F	109.5	C2D—C13D—H13L	109.5
H13D—C13B—H13E	109.5	H13J—C13D—H13K	109.5
H13D—C13B—H13F	109.5	H13J—C13D—H13L	109.5
H13E—C13B—H13F	109.5	H13K—C13D—H13L	109.5
O1A—C3A—C4A—C5A	−177.7 (4)	O1C—C3C—C4C—C5C	176.0 (4)
N1A—C1A—C2A—C3A	177.7 (4)	N1C—C1C—C2C—C3C	−179.4 (4)
N1A—C1A—C2A—C12A	−65.4 (5)	N1C—C1C—C2C—C12C	64.6 (5)
N1A—C1A—C2A—C13A	61.8 (5)	N1C—C1C—C2C—C13C	−62.7 (5)
N1A—C1A—C5A—C4A	−176.8 (3)	N1C—C1C—C5C—C4C	178.2 (3)
N1A—C1A—C5A—C6A	0.4 (4)	N1C—C1C—C5C—C6C	−0.8 (4)
C1A—N1A—C11A—C6A	−0.6 (4)	C1C—N1C—C11C—C6C	0.0 (4)
C1A—N1A—C11A—C10A	178.3 (3)	C1C—N1C—C11C—C10C	−178.5 (3)
C1A—C2A—C3A—O1A	178.3 (4)	C1C—C2C—C3C—O1C	−176.9 (4)
C1A—C2A—C3A—C4A	−1.8 (4)	C1C—C2C—C3C—C4C	1.1 (4)
C1A—C5A—C6A—C7A	−179.2 (4)	C1C—C5C—C6C—C7C	179.9 (4)
C1A—C5A—C6A—C11A	−0.8 (3)	C1C—C5C—C6C—C11C	0.7 (3)
C2A—C1A—C5A—C4A	1.0 (4)	C2C—C1C—C5C—C4C	−1.5 (4)
C2A—C1A—C5A—C6A	178.3 (3)	C2C—C1C—C5C—C6C	179.5 (3)
C2A—C3A—C4A—C5A	2.3 (4)	C2C—C3C—C4C—C5C	−1.9 (4)
C3A—C4A—C5A—C1A	−2.0 (4)	C3C—C4C—C5C—C1C	2.1 (4)
C3A—C4A—C5A—C6A	−177.9 (4)	C3C—C4C—C5C—C6C	−179.5 (4)
C4A—C5A—C6A—C7A	−3.1 (7)	C4C—C5C—C6C—C7C	1.4 (7)
C4A—C5A—C6A—C11A	175.2 (4)	C4C—C5C—C6C—C11C	−177.7 (4)
C5A—C1A—C2A—C3A	0.5 (4)	C5C—C1C—C2C—C3C	0.2 (4)
C5A—C1A—C2A—C12A	117.4 (4)	C5C—C1C—C2C—C12C	−115.8 (4)
C5A—C1A—C2A—C13A	−115.4 (4)	C5C—C1C—C2C—C13C	116.9 (4)
C5A—C6A—C7A—C8A	177.2 (3)	C5C—C6C—C7C—C8C	−179.1 (3)
C5A—C6A—C11A—N1A	0.8 (3)	C5C—C6C—C11C—N1C	−0.4 (3)
C5A—C6A—C11A—C10A	−178.2 (3)	C5C—C6C—C11C—C10C	178.1 (3)
C6A—C7A—C8A—C9A	0.7 (5)	C6C—C7C—C8C—C9C	0.7 (5)
C7A—C6A—C11A—N1A	179.5 (3)	C7C—C6C—C11C—N1C	−179.8 (3)
C7A—C6A—C11A—C10A	0.5 (5)	C7C—C6C—C11C—C10C	−1.2 (5)
C7A—C8A—C9A—C10A	0.3 (5)	C7C—C8C—C9C—C10C	−0.2 (6)
C8A—C9A—C10A—C11A	−0.9 (5)	C8C—C9C—C10C—C11C	−0.9 (5)
C9A—C10A—C11A—N1A	−178.3 (3)	C9C—C10C—C11C—N1C	179.8 (3)
C9A—C10A—C11A—C6A	0.5 (5)	C9C—C10C—C11C—C6C	1.6 (5)
C11A—N1A—C1A—C2A	−177.2 (4)	C11C—N1C—C1C—C2C	−179.8 (3)
C11A—N1A—C1A—C5A	0.1 (4)	C11C—N1C—C1C—C5C	0.5 (4)
C11A—C6A—C7A—C8A	−1.1 (5)	C11C—C6C—C7C—C8C	0.0 (5)
C12A—C2A—C3A—O1A	58.9 (5)	C12C—C2C—C3C—O1C	−57.9 (5)
C12A—C2A—C3A—C4A	−121.2 (3)	C12C—C2C—C3C—C4C	120.1 (3)
C13A—C2A—C3A—O1A	−63.2 (5)	C13C—C2C—C3C—O1C	63.6 (5)
C13A—C2A—C3A—C4A	116.8 (4)	C13C—C2C—C3C—C4C	−118.4 (3)
O1B—C3B—C4B—C5B	174.0 (4)	O1D—C3D—C4D—C5D	175.3 (4)
N1B—C1B—C2B—C3B	177.2 (4)	N1D—C1D—C2D—C3D	178.6 (4)
N1B—C1B—C2B—C12B	−66.0 (5)	N1D—C1D—C2D—C12D	−64.4 (5)
N1B—C1B—C2B—C13B	61.2 (5)	N1D—C1D—C2D—C13D	63.4 (5)
N1B—C1B—C5B—C4B	179.8 (3)	N1D—C1D—C5D—C4D	178.9 (3)
N1B—C1B—C5B—C6B	0.0 (4)	N1D—C1D—C5D—C6D	0.0 (4)
C1B—N1B—C11B—C6B	0.6 (4)	C1D—N1D—C11D—C6D	−0.1 (4)
C1B—N1B—C11B—C10B	−177.7 (4)	C1D—N1D—C11D—C10D	−179.2 (4)
C1B—C2B—C3B—O1B	−174.5 (4)	C1D—C2D—C3D—O1D	−176.7 (4)
C1B—C2B—C3B—C4B	4.4 (4)	C1D—C2D—C3D—C4D	1.5 (4)
C1B—C5B—C6B—C7B	178.4 (4)	C1D—C5D—C6D—C7D	179.6 (4)
C1B—C5B—C6B—C11B	0.3 (4)	C1D—C5D—C6D—C11D	0.0 (4)
C2B—C1B—C5B—C4B	−0.6 (5)	C2D—C1D—C5D—C4D	−2.7 (5)
C2B—C1B—C5B—C6B	179.6 (3)	C2D—C1D—C5D—C6D	178.4 (3)
C2B—C3B—C4B—C5B	−4.8 (4)	C2D—C3D—C4D—C5D	−2.9 (4)
C3B—C4B—C5B—C1B	3.3 (4)	C3D—C4D—C5D—C1D	3.3 (4)
C3B—C4B—C5B—C6B	−177.1 (5)	C3D—C4D—C5D—C6D	−178.3 (5)
C4B—C5B—C6B—C7B	−1.2 (8)	C4D—C5D—C6D—C7D	1.2 (9)
C4B—C5B—C6B—C11B	−179.3 (5)	C4D—C5D—C6D—C11D	−178.5 (5)
C5B—C1B—C2B—C3B	−2.3 (4)	C5D—C1D—C2D—C3D	0.7 (4)
C5B—C1B—C2B—C12B	114.6 (4)	C5D—C1D—C2D—C12D	117.6 (4)
C5B—C1B—C2B—C13B	−118.3 (4)	C5D—C1D—C2D—C13D	−114.5 (4)
C5B—C6B—C7B—C8B	−177.4 (4)	C5D—C6D—C7D—C8D	−178.8 (4)
C5B—C6B—C11B—N1B	−0.5 (4)	C5D—C6D—C11D—N1D	0.1 (4)
C5B—C6B—C11B—C10B	177.8 (3)	C5D—C6D—C11D—C10D	179.2 (3)
C6B—C7B—C8B—C9B	0.0 (5)	C6D—C7D—C8D—C9D	−0.5 (6)
C7B—C6B—C11B—N1B	−179.0 (3)	C7D—C6D—C11D—N1D	−179.6 (3)
C7B—C6B—C11B—C10B	−0.6 (5)	C7D—C6D—C11D—C10D	−0.5 (6)
C7B—C8B—C9B—C10B	−0.3 (6)	C7D—C8D—C9D—C10D	−0.3 (6)
C8B—C9B—C10B—C11B	0.2 (6)	C8D—C9D—C10D—C11D	0.7 (6)
C9B—C10B—C11B—N1B	178.3 (4)	C9D—C10D—C11D—N1D	178.7 (4)
C9B—C10B—C11B—C6B	0.3 (5)	C9D—C10D—C11D—C6D	−0.3 (5)
C11B—N1B—C1B—C2B	−179.9 (4)	C11D—N1D—C1D—C2D	−177.9 (4)
C11B—N1B—C1B—C5B	−0.4 (4)	C11D—N1D—C1D—C5D	0.1 (4)
C11B—C6B—C7B—C8B	0.5 (5)	C11D—C6D—C7D—C8D	0.9 (6)
C12B—C2B—C3B—O1B	66.5 (5)	C12D—C2D—C3D—O1D	64.2 (5)
C12B—C2B—C3B—C4B	−114.6 (3)	C12D—C2D—C3D—C4D	−117.5 (4)
C13B—C2B—C3B—O1B	−55.2 (5)	C13D—C2D—C3D—O1D	−58.2 (5)
C13B—C2B—C3B—C4B	123.7 (3)	C13D—C2D—C3D—C4D	120.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C9B—H9B···O1Bi	0.95	2.51	3.427 (4)	162
C10B—H10B···O1A	0.95	2.61	3.379 (5)	139
C12B—H12D···O1Cii	0.98	2.73	3.497 (6)	136
C9D—H9D···O1Diii	0.95	2.46	3.372 (4)	161
C10D—H10D···O1Cii	0.95	2.46	3.274 (5)	144
C12D—H12J···O1Aiv	0.98	2.69	3.485 (6)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9B—H9B⋯O1B i	0.95	2.51	3.427 (4)	162
C10B—H10B⋯O1A	0.95	2.61	3.379 (5)	139
C12B—H12D⋯O1C ii	0.98	2.73	3.497 (6)	136
C9D—H9D⋯O1D iii	0.95	2.46	3.372 (4)	161
C10D—H10D⋯O1C ii	0.95	2.46	3.274 (5)	144
C12D—H12J⋯O1A iv	0.98	2.69	3.485 (6)	138

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .