Synthesis and structural study of organic two-photon-absorbing cyclo­alkanone chromophores

The three organic two-photon-absorbing cyclo­alkanone chromophores 2,4-bis­[4-(di­ethyl­amino)­benzyl­idene]cyclo­butanone, C₂₆H₃₂N₂O (I), 2,5-bis­[4-(di­ethyl­amino)­benzyl­idene]cyclo­penta­none, C₂₇H₃₄N₂O (II), and 2,6-bis­[4-(di­ethyl­amino)­benzyl­idene]cyclo­hexa­none, C₂₈H₃₆N₂O (III), were obtained by a reaction between 4-(di­ethyl­amino)­benzaldehyde and the corresponding cyclo­alkanone and were characterized by single-crystal X-ray diffraction studies, as well as density functional theory (DFT) quantum-chemical calculations. Mol­ecules of this series have three main fragments, i.e. central acceptor (A) and two terminal donors (D₁ and D₂) and represent examples of the D₁–π–A–π–D₂ mol­ecular design. All three com­pounds crystallize with two crystallographically independent mol­ecules in the asymmetric unit (A and B) and are distinguished by the conformations of both the mol­ecular Et₂N—C₆H₄—C=C—C(=O)—C=C—C₆H₄—NEt₂ backbone (arcuate or linear) and the terminal di­ethyl­amino substituents (syn- or anti­periplanar to the plane of the mol­ecule). The central four- and five-membered rings in I and II are almost planar, and the six-membered ring in III adopts a sofa conformation. In the crystals of I–III, the two independent mol­ecules A and B form hydrogen-bonded [A...B] dimers via inter­molecular C—H...O hydrogen bonds. Furthermore, the [A...B] dimers in I are bound by inter­molecular C—H...O hydrogen bonds into two-tier puckered layers, whereas in the crystals of II and III, the [A...B] dimers are stacked along the c and a axes, respectively. Taking into account the decreasing steric strain upon expanding the central ring, com­pound I might be more efficient as a two-photon absorption chromophore than com­pounds II and III, which corresponds to the results of spectroscopic studies.

Computing details

For all structures, data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2015a); software used to prepare material for publication: SHELXTL (Sheldrick, 2015a).

2,4-Bis[4-(diethylamino)benzylidene]cyclobutanone (I)

Crystal data

C26H32N2O	F(000) = 1680
Mr = 388.53	Dx = 1.195 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.491 (3) Å	Cell parameters from 9766 reflections
b = 16.604 (3) Å	θ = 4.2–30.6°
c = 15.170 (3) Å	µ = 0.07 mm^−1
β = 101.362 (2)°	T = 100 K
V = 4319.6 (13) Å^3	Block, red
Z = 8	0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer	11185 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
φ and ω scans	θmax = 30.6°, θmin = 4.3°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −25→25
Tmin = 0.669, Tmax = 0.746	k = −23→22
50803 measured reflections	l = −21→21
13212 independent reflections

Refinement

Refinement on F^2	Primary atom site location: difference Fourier map
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.131	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0744P)^2 + 1.2459P] where P = (Fo^2 + 2Fc^2)/3
13212 reflections	(Δ/σ)max = 0.001
530 parameters	Δρmax = 0.51 e Å^−3
6 restraints	Δρmin = −0.55 e Å^−3

Special details

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. The single crystal X-ray diffraction data were collected on a Bruker SMART APEX II diffractometer equipped with CCD area detector (λMoKa-radiation, graphite monochromator, φ- and ω-scan mode). The semi-empirical absorption correction was applied using the SADABS program (Bruker, 2016). The structures were determined by direct methods and refined by full-matrix least-square technique on F² in anisotropic approximation for non-hydrogen atoms.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1A	0.37645 (4)	0.53087 (5)	0.75324 (5)	0.02283 (15)
N1A	0.76212 (5)	0.61944 (6)	0.45699 (6)	0.02425 (18)
N2A	0.04010 (5)	0.69477 (5)	0.26520 (5)	0.01993 (16)
C1A	0.37999 (5)	0.55390 (5)	0.67763 (6)	0.01722 (17)
C2A	0.44488 (5)	0.56834 (6)	0.62885 (6)	0.01699 (16)
C3A	0.38715 (5)	0.59537 (6)	0.54497 (6)	0.01688 (16)
H3A	0.3850	0.5595	0.4924	0.020*
H3B	0.3929	0.6524	0.5285	0.020*
C4A	0.32212 (5)	0.58049 (6)	0.59758 (6)	0.01716 (17)
C5A	0.52270 (5)	0.56130 (6)	0.65452 (6)	0.01822 (17)
H5A	0.5410	0.5426	0.7141	0.022*
C6A	0.58238 (5)	0.57866 (6)	0.60288 (6)	0.01809 (17)
C7A	0.66150 (6)	0.57242 (6)	0.64341 (7)	0.02256 (19)
H7A	0.6748	0.5579	0.7051	0.027*
C8A	0.72083 (6)	0.58656 (7)	0.59713 (7)	0.0243 (2)
H8A	0.7736	0.5818	0.6276	0.029*
C9A	0.70416 (6)	0.60794 (6)	0.50519 (7)	0.02049 (18)
C10A	0.62447 (6)	0.61652 (6)	0.46474 (6)	0.02010 (18)
H10A	0.6109	0.6328	0.4036	0.024*
C11A	0.56598 (5)	0.60182 (6)	0.51204 (6)	0.01917 (18)
H11A	0.5132	0.6076	0.4822	0.023*
C12A	0.84282 (6)	0.59702 (7)	0.49353 (8)	0.02812 (17)	0.95
H12A	0.8674	0.5784	0.4437	0.034*	0.95
H12B	0.8432	0.5514	0.5356	0.034*	0.95
C13A	0.89141 (6)	0.66534 (7)	0.54274 (8)	0.02812 (17)	0.95
H13A	0.9447	0.6463	0.5655	0.042*	0.95
H13B	0.8683	0.6833	0.5932	0.042*	0.95
H13C	0.8926	0.7103	0.5012	0.042*	0.95
C12C	0.8326 (6)	0.6515 (10)	0.5144 (13)	0.02812 (17)	0.05
H12E	0.8188	0.6747	0.5693	0.034*	0.05
H12F	0.8537	0.6955	0.4821	0.034*	0.05
C13C	0.8957 (11)	0.5878 (12)	0.5417 (15)	0.02812 (17)	0.05
H13G	0.9410	0.6121	0.5810	0.042*	0.05
H13H	0.9113	0.5662	0.4878	0.042*	0.05
H13I	0.8752	0.5441	0.5738	0.042*	0.05
C14A	0.74330 (6)	0.64558 (6)	0.36366 (6)	0.0242 (2)
H14A	0.6995	0.6126	0.3312	0.029*
H14B	0.7889	0.6357	0.3355	0.029*
C15A	0.72088 (7)	0.73443 (6)	0.35250 (7)	0.0270 (2)
H15A	0.7066	0.7475	0.2884	0.041*
H15B	0.7652	0.7678	0.3807	0.041*
H15C	0.6764	0.7450	0.3813	0.041*
C16A	0.24366 (5)	0.58555 (6)	0.58170 (6)	0.01789 (17)
H16A	0.2190	0.5694	0.6293	0.021*
C17A	0.19264 (5)	0.61292 (6)	0.49984 (6)	0.01736 (17)
C18A	0.22053 (5)	0.64413 (6)	0.42601 (7)	0.02070 (18)
H18A	0.2752	0.6471	0.4291	0.025*
C19A	0.17103 (6)	0.67060 (6)	0.34919 (6)	0.02036 (18)
H19A	0.1923	0.6914	0.3009	0.024*
C20A	0.08918 (5)	0.66731 (6)	0.34106 (6)	0.01725 (17)
C21A	0.06071 (5)	0.63396 (6)	0.41418 (7)	0.01977 (18)
H21A	0.0061	0.6291	0.4105	0.024*
C22A	0.11126 (5)	0.60833 (6)	0.49103 (6)	0.01899 (17)
H22A	0.0903	0.5870	0.5393	0.023*
C23A	−0.04420 (5)	0.68533 (6)	0.25203 (7)	0.02092 (18)
H23A	−0.0561	0.6338	0.2793	0.025*
H23B	−0.0662	0.6825	0.1868	0.025*
C24A	−0.08338 (6)	0.75382 (7)	0.29300 (8)	0.0262 (2)
H24A	−0.0684	0.8054	0.2699	0.039*
H24B	−0.0668	0.7527	0.3586	0.039*
H24C	−0.1401	0.7475	0.2769	0.039*
C25A	0.06782 (6)	0.74524 (6)	0.19923 (6)	0.02031 (18)
H25A	0.1172	0.7714	0.2284	0.024*
H25B	0.0291	0.7882	0.1792	0.024*
C26A	0.08147 (8)	0.69863 (7)	0.11760 (8)	0.0303 (2)
H26A	0.0964	0.7360	0.0740	0.046*
H26B	0.0335	0.6705	0.0899	0.046*
H26C	0.1233	0.6593	0.1362	0.046*
O1B	0.10286 (4)	0.50910 (5)	0.69592 (5)	0.02444 (15)
N1B	0.42893 (5)	0.72757 (5)	1.15936 (5)	0.01779 (15)
N2B	−0.27827 (5)	0.56142 (5)	1.00784 (6)	0.02164 (17)
C1B	0.09625 (5)	0.54128 (6)	0.76664 (6)	0.01794 (17)
C2B	0.14987 (5)	0.58571 (6)	0.83853 (6)	0.01724 (17)
C3B	0.08455 (5)	0.59823 (6)	0.89097 (6)	0.01810 (17)
H3C	0.0689	0.6552	0.8952	0.022*
H3D	0.0940	0.5718	0.9506	0.022*
C4B	0.03144 (5)	0.55029 (6)	0.81680 (6)	0.01799 (17)
C5B	0.22691 (5)	0.60113 (6)	0.85074 (6)	0.01750 (17)
H5B	0.2518	0.5858	0.8031	0.021*
C6B	0.27628 (5)	0.63841 (6)	0.92814 (6)	0.01666 (16)
C7B	0.35677 (5)	0.64570 (6)	0.93137 (6)	0.01787 (17)
H7B	0.3774	0.6298	0.8806	0.021*
C8B	0.40705 (5)	0.67539 (6)	1.00641 (6)	0.01830 (17)
H8B	0.4611	0.6799	1.0057	0.022*
C9B	0.37940 (5)	0.69916 (5)	1.08398 (6)	0.01633 (16)
C10B	0.29807 (5)	0.69378 (6)	1.07972 (6)	0.01883 (17)
H10B	0.2771	0.7105	1.1299	0.023*
C11B	0.24859 (5)	0.66480 (6)	1.00413 (6)	0.01914 (17)
H11B	0.1942	0.6626	1.0034	0.023*
C12B	0.51320 (6)	0.72303 (6)	1.16656 (7)	0.02174 (19)
H12C	0.5386	0.7583	1.2164	0.026*
H12D	0.5264	0.7441	1.1104	0.026*
C13B	0.54639 (7)	0.63832 (7)	1.18309 (8)	0.0294 (2)
H13D	0.5223	0.6031	1.1335	0.044*
H13E	0.5352	0.6176	1.2397	0.044*
H13F	0.6029	0.6398	1.1867	0.044*
C14B	0.40059 (6)	0.74570 (6)	1.24138 (6)	0.02146 (18)
H14C	0.3510	0.7759	1.2250	0.026*
H14D	0.4388	0.7813	1.2796	0.026*
C15B	0.38688 (8)	0.67211 (8)	1.29628 (8)	0.0318 (2)
H15D	0.3481	0.6370	1.2596	0.048*
H15E	0.3677	0.6894	1.3498	0.048*
H15F	0.4360	0.6426	1.3147	0.048*
C16B	−0.04263 (5)	0.52305 (6)	0.80021 (6)	0.01855 (17)
H16B	−0.0582	0.4928	0.7465	0.022*
C17B	−0.10155 (5)	0.53432 (6)	0.85449 (6)	0.01752 (17)
C18B	−0.08797 (6)	0.57509 (6)	0.93738 (7)	0.02055 (18)
H18B	−0.0375	0.5964	0.9600	0.025*
C19B	−0.14554 (6)	0.58523 (6)	0.98702 (7)	0.02076 (18)
H19B	−0.1339	0.6138	1.0423	0.025*
C20B	−0.22168 (5)	0.55394 (6)	0.95719 (6)	0.01812 (17)
C21B	−0.23569 (5)	0.51384 (6)	0.87339 (6)	0.01852 (17)
H21B	−0.2862	0.4930	0.8502	0.022*
C22B	−0.17738 (5)	0.50434 (6)	0.82442 (6)	0.01814 (17)
H22B	−0.1890	0.4766	0.7686	0.022*
C23B	−0.35851 (6)	0.53606 (6)	0.97335 (7)	0.0239 (2)
H23C	−0.3843	0.5262	1.0249	0.029*
H23D	−0.3576	0.4844	0.9410	0.029*
C24B	−0.40725 (6)	0.59653 (7)	0.91006 (8)	0.0300 (2)
H24D	−0.3816	0.6078	0.8595	0.045*
H24E	−0.4122	0.6466	0.9427	0.045*
H24F	−0.4592	0.5740	0.8874	0.045*
C25B	−0.26112 (6)	0.59867 (6)	1.09690 (7)	0.0240 (2)
H25C	−0.2071	0.5847	1.1265	0.029*
H25D	−0.2967	0.5760	1.1338	0.029*
C26B	−0.26962 (7)	0.69010 (7)	1.09414 (8)	0.0298 (2)
H26D	−0.2361	0.7128	1.0557	0.045*
H26E	−0.2542	0.7118	1.1551	0.045*
H26F	−0.3241	0.7044	1.0698	0.045*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0237 (3)	0.0277 (4)	0.0181 (3)	0.0044 (3)	0.0067 (3)	0.0023 (3)
N1A	0.0160 (4)	0.0309 (4)	0.0265 (4)	−0.0018 (3)	0.0059 (3)	0.0014 (3)
N2A	0.0154 (3)	0.0264 (4)	0.0177 (4)	0.0002 (3)	0.0026 (3)	0.0013 (3)
C1A	0.0170 (4)	0.0171 (4)	0.0179 (4)	0.0021 (3)	0.0043 (3)	−0.0015 (3)
C2A	0.0169 (4)	0.0180 (4)	0.0162 (4)	0.0011 (3)	0.0034 (3)	−0.0011 (3)
C3A	0.0155 (4)	0.0186 (4)	0.0166 (4)	0.0007 (3)	0.0034 (3)	−0.0003 (3)
C4A	0.0166 (4)	0.0188 (4)	0.0164 (4)	0.0010 (3)	0.0040 (3)	−0.0004 (3)
C5A	0.0174 (4)	0.0200 (4)	0.0167 (4)	0.0012 (3)	0.0021 (3)	−0.0008 (3)
C6A	0.0154 (4)	0.0193 (4)	0.0191 (4)	0.0010 (3)	0.0021 (3)	−0.0009 (3)
C7A	0.0171 (4)	0.0282 (5)	0.0209 (4)	0.0009 (4)	0.0003 (3)	0.0033 (4)
C8A	0.0152 (4)	0.0303 (5)	0.0260 (5)	0.0002 (4)	0.0011 (3)	0.0032 (4)
C9A	0.0161 (4)	0.0213 (4)	0.0240 (5)	−0.0015 (3)	0.0039 (3)	0.0004 (3)
C10A	0.0169 (4)	0.0243 (4)	0.0187 (4)	−0.0010 (3)	0.0027 (3)	−0.0004 (3)
C11A	0.0149 (4)	0.0229 (4)	0.0190 (4)	0.0009 (3)	0.0015 (3)	−0.0011 (3)
C12A	0.0192 (3)	0.0336 (4)	0.0317 (4)	−0.0024 (3)	0.0053 (3)	−0.0099 (3)
C13A	0.0192 (3)	0.0336 (4)	0.0317 (4)	−0.0024 (3)	0.0053 (3)	−0.0099 (3)
C12C	0.0192 (3)	0.0336 (4)	0.0317 (4)	−0.0024 (3)	0.0053 (3)	−0.0099 (3)
C13C	0.0192 (3)	0.0336 (4)	0.0317 (4)	−0.0024 (3)	0.0053 (3)	−0.0099 (3)
C14A	0.0222 (5)	0.0279 (5)	0.0245 (5)	−0.0025 (4)	0.0094 (4)	−0.0019 (4)
C15A	0.0300 (5)	0.0284 (5)	0.0252 (5)	−0.0002 (4)	0.0116 (4)	−0.0002 (4)
C16A	0.0166 (4)	0.0205 (4)	0.0173 (4)	0.0003 (3)	0.0052 (3)	0.0000 (3)
C17A	0.0149 (4)	0.0199 (4)	0.0177 (4)	0.0004 (3)	0.0041 (3)	−0.0007 (3)
C18A	0.0142 (4)	0.0282 (5)	0.0202 (4)	−0.0006 (3)	0.0047 (3)	0.0021 (4)
C19A	0.0164 (4)	0.0270 (5)	0.0183 (4)	−0.0008 (3)	0.0051 (3)	0.0017 (3)
C20A	0.0165 (4)	0.0184 (4)	0.0169 (4)	0.0006 (3)	0.0032 (3)	−0.0027 (3)
C21A	0.0143 (4)	0.0245 (4)	0.0210 (4)	0.0002 (3)	0.0047 (3)	0.0008 (3)
C22A	0.0159 (4)	0.0227 (4)	0.0195 (4)	0.0007 (3)	0.0063 (3)	0.0010 (3)
C23A	0.0158 (4)	0.0231 (4)	0.0225 (4)	−0.0015 (3)	0.0004 (3)	−0.0010 (3)
C24A	0.0196 (4)	0.0278 (5)	0.0327 (5)	0.0009 (4)	0.0088 (4)	−0.0005 (4)
C25A	0.0204 (4)	0.0212 (4)	0.0192 (4)	0.0016 (3)	0.0036 (3)	0.0013 (3)
C26A	0.0412 (6)	0.0299 (5)	0.0227 (5)	0.0039 (5)	0.0132 (4)	0.0000 (4)
O1B	0.0249 (4)	0.0298 (4)	0.0203 (3)	−0.0054 (3)	0.0088 (3)	−0.0062 (3)
N1B	0.0163 (3)	0.0204 (4)	0.0167 (3)	−0.0013 (3)	0.0033 (3)	−0.0004 (3)
N2B	0.0185 (4)	0.0248 (4)	0.0230 (4)	−0.0011 (3)	0.0073 (3)	−0.0020 (3)
C1B	0.0180 (4)	0.0183 (4)	0.0178 (4)	−0.0002 (3)	0.0042 (3)	0.0008 (3)
C2B	0.0174 (4)	0.0188 (4)	0.0158 (4)	0.0008 (3)	0.0039 (3)	0.0000 (3)
C3B	0.0155 (4)	0.0217 (4)	0.0173 (4)	0.0005 (3)	0.0037 (3)	−0.0018 (3)
C4B	0.0174 (4)	0.0193 (4)	0.0177 (4)	0.0006 (3)	0.0042 (3)	−0.0013 (3)
C5B	0.0177 (4)	0.0196 (4)	0.0158 (4)	0.0008 (3)	0.0047 (3)	0.0002 (3)
C6B	0.0154 (4)	0.0188 (4)	0.0162 (4)	0.0002 (3)	0.0042 (3)	0.0013 (3)
C7B	0.0172 (4)	0.0218 (4)	0.0157 (4)	−0.0013 (3)	0.0057 (3)	0.0009 (3)
C8B	0.0155 (4)	0.0224 (4)	0.0181 (4)	−0.0020 (3)	0.0059 (3)	0.0011 (3)
C9B	0.0172 (4)	0.0153 (4)	0.0167 (4)	−0.0006 (3)	0.0038 (3)	0.0016 (3)
C10B	0.0163 (4)	0.0232 (4)	0.0178 (4)	0.0007 (3)	0.0054 (3)	−0.0018 (3)
C11B	0.0147 (4)	0.0241 (4)	0.0193 (4)	0.0010 (3)	0.0049 (3)	−0.0014 (3)
C12B	0.0168 (4)	0.0260 (5)	0.0221 (4)	−0.0034 (3)	0.0030 (3)	−0.0005 (4)
C13B	0.0234 (5)	0.0350 (6)	0.0301 (5)	0.0083 (4)	0.0058 (4)	0.0046 (4)
C14B	0.0221 (4)	0.0249 (5)	0.0178 (4)	−0.0012 (4)	0.0048 (3)	−0.0037 (3)
C15B	0.0368 (6)	0.0373 (6)	0.0238 (5)	0.0010 (5)	0.0123 (4)	0.0064 (4)
C16B	0.0184 (4)	0.0190 (4)	0.0185 (4)	−0.0006 (3)	0.0040 (3)	−0.0017 (3)
C17B	0.0160 (4)	0.0182 (4)	0.0186 (4)	−0.0003 (3)	0.0037 (3)	−0.0007 (3)
C18B	0.0163 (4)	0.0243 (4)	0.0209 (4)	−0.0027 (3)	0.0034 (3)	−0.0039 (3)
C19B	0.0187 (4)	0.0249 (4)	0.0189 (4)	−0.0014 (3)	0.0041 (3)	−0.0039 (3)
C20B	0.0172 (4)	0.0176 (4)	0.0201 (4)	0.0008 (3)	0.0048 (3)	0.0014 (3)
C21B	0.0158 (4)	0.0186 (4)	0.0207 (4)	−0.0013 (3)	0.0026 (3)	0.0001 (3)
C22B	0.0173 (4)	0.0181 (4)	0.0185 (4)	−0.0010 (3)	0.0023 (3)	−0.0012 (3)
C23B	0.0186 (4)	0.0256 (5)	0.0295 (5)	−0.0030 (4)	0.0093 (4)	−0.0002 (4)
C24B	0.0214 (5)	0.0317 (5)	0.0365 (6)	0.0012 (4)	0.0045 (4)	−0.0012 (4)
C25B	0.0261 (5)	0.0267 (5)	0.0209 (5)	0.0024 (4)	0.0091 (4)	0.0016 (4)
C26B	0.0374 (6)	0.0271 (5)	0.0269 (5)	−0.0002 (4)	0.0112 (4)	−0.0024 (4)

Geometric parameters (Å, º)

O1A—C1A	1.2222 (12)	C26A—H26A	0.9800
N1A—C9A	1.3752 (13)	C26A—H26B	0.9800
N1A—C14A	1.4554 (12)	C26A—H26C	0.9800
N1A—C12A	1.4594 (12)	O1B—C1B	1.2243 (12)
N1A—C12C	1.463 (2)	N1B—C9B	1.3748 (12)
N2A—C20A	1.3711 (12)	N1B—C12B	1.4585 (12)
N2A—C23A	1.4570 (12)	N1B—C14B	1.4586 (12)
N2A—C25A	1.4596 (13)	N2B—C20B	1.3732 (12)
C1A—C4A	1.4866 (13)	N2B—C23B	1.4601 (13)
C1A—C2A	1.4914 (13)	N2B—C25B	1.4622 (14)
C2A—C5A	1.3450 (13)	C1B—C2B	1.4867 (13)
C2A—C3A	1.5277 (13)	C1B—C4B	1.4921 (13)
C3A—C4A	1.5329 (13)	C2B—C5B	1.3481 (13)
C3A—H3A	0.9900	C2B—C3B	1.5295 (13)
C3A—H3B	0.9900	C3B—C4B	1.5333 (13)
C4A—C16A	1.3484 (13)	C3B—H3C	0.9900
C5A—C6A	1.4521 (13)	C3B—H3D	0.9900
C5A—H5A	0.9500	C4B—C16B	1.3482 (13)
C6A—C7A	1.4032 (13)	C5B—C6B	1.4518 (13)
C6A—C11A	1.4049 (13)	C5B—H5B	0.9500
C7A—C8A	1.3826 (14)	C6B—C7B	1.4044 (13)
C7A—H7A	0.9500	C6B—C11B	1.4055 (13)
C8A—C9A	1.4129 (15)	C7B—C8B	1.3848 (13)
C8A—H8A	0.9500	C7B—H7B	0.9500
C9A—C10A	1.4151 (13)	C8B—C9B	1.4137 (13)
C10A—C11A	1.3821 (13)	C8B—H8B	0.9500
C10A—H10A	0.9500	C9B—C10B	1.4141 (13)
C11A—H11A	0.9500	C10B—C11B	1.3800 (13)
C12A—C13A	1.5220 (13)	C10B—H10B	0.9500
C12A—H12A	0.9900	C11B—H11B	0.9500
C12A—H12B	0.9900	C12B—C13B	1.5236 (15)
C13A—H13A	0.9800	C12B—H12C	0.9900
C13A—H13B	0.9800	C12B—H12D	0.9900
C13A—H13C	0.9800	C13B—H13D	0.9800
C12C—C13C	1.526 (2)	C13B—H13E	0.9800
C12C—H12E	0.9900	C13B—H13F	0.9800
C12C—H12F	0.9900	C14B—C15B	1.5241 (16)
C13C—H13G	0.9800	C14B—H14C	0.9900
C13C—H13H	0.9800	C14B—H14D	0.9900
C13C—H13I	0.9800	C15B—H15D	0.9800
C14A—C15A	1.5273 (13)	C15B—H15E	0.9800
C14A—H14A	0.9900	C15B—H15F	0.9800
C14A—H14B	0.9900	C16B—C17B	1.4524 (13)
C15A—H15A	0.9800	C16B—H16B	0.9500
C15A—H15B	0.9800	C17B—C22B	1.4060 (13)
C15A—H15C	0.9800	C17B—C18B	1.4065 (13)
C16A—C17A	1.4519 (13)	C18B—C19B	1.3815 (13)
C16A—H16A	0.9500	C18B—H18B	0.9500
C17A—C22A	1.4053 (13)	C19B—C20B	1.4180 (13)
C17A—C18A	1.4058 (13)	C19B—H19B	0.9500
C18A—C19A	1.3796 (13)	C20B—C21B	1.4130 (13)
C18A—H18A	0.9500	C21B—C22B	1.3840 (13)
C19A—C20A	1.4138 (13)	C21B—H21B	0.9500
C19A—H19A	0.9500	C22B—H22B	0.9500
C20A—C21A	1.4151 (13)	C23B—C24B	1.5278 (16)
C21A—C22A	1.3842 (13)	C23B—H23C	0.9900
C21A—H21A	0.9500	C23B—H23D	0.9900
C22A—H22A	0.9500	C24B—H24D	0.9800
C23A—C24A	1.5222 (15)	C24B—H24E	0.9800
C23A—H23A	0.9900	C24B—H24F	0.9800
C23A—H23B	0.9900	C25B—C26B	1.5251 (16)
C24A—H24A	0.9800	C25B—H25C	0.9900
C24A—H24B	0.9800	C25B—H25D	0.9900
C24A—H24C	0.9800	C26B—H26D	0.9800
C25A—C26A	1.5185 (15)	C26B—H26E	0.9800
C25A—H25A	0.9900	C26B—H26F	0.9800
C25A—H25B	0.9900
C9A—N1A—C14A	120.63 (8)	H25A—C25A—H25B	107.8
C9A—N1A—C12A	121.46 (9)	C25A—C26A—H26A	109.5
C14A—N1A—C12A	117.52 (9)	C25A—C26A—H26B	109.5
C9A—N1A—C12C	110.9 (9)	H26A—C26A—H26B	109.5
C14A—N1A—C12C	118.3 (9)	C25A—C26A—H26C	109.5
C20A—N2A—C23A	121.92 (8)	H26A—C26A—H26C	109.5
C20A—N2A—C25A	121.93 (8)	H26B—C26A—H26C	109.5
C23A—N2A—C25A	115.57 (8)	C9B—N1B—C12B	120.43 (8)
O1A—C1A—C4A	135.01 (9)	C9B—N1B—C14B	121.07 (8)
O1A—C1A—C2A	134.44 (9)	C12B—N1B—C14B	117.07 (8)
C4A—C1A—C2A	90.53 (7)	C20B—N2B—C23B	121.43 (8)
C5A—C2A—C1A	131.92 (9)	C20B—N2B—C25B	121.07 (8)
C5A—C2A—C3A	137.04 (9)	C23B—N2B—C25B	117.45 (8)
C1A—C2A—C3A	91.02 (7)	O1B—C1B—C2B	134.80 (9)
C2A—C3A—C4A	87.45 (7)	O1B—C1B—C4B	134.67 (9)
C2A—C3A—H3A	114.1	C2B—C1B—C4B	90.52 (7)
C4A—C3A—H3A	114.1	C5B—C2B—C1B	131.61 (9)
C2A—C3A—H3B	114.1	C5B—C2B—C3B	137.02 (9)
C4A—C3A—H3B	114.1	C1B—C2B—C3B	91.21 (7)
H3A—C3A—H3B	111.3	C2B—C3B—C4B	87.39 (7)
C16A—C4A—C1A	132.05 (9)	C2B—C3B—H3C	114.1
C16A—C4A—C3A	136.93 (9)	C4B—C3B—H3C	114.1
C1A—C4A—C3A	91.00 (7)	C2B—C3B—H3D	114.1
C2A—C5A—C6A	128.36 (9)	C4B—C3B—H3D	114.1
C2A—C5A—H5A	115.8	H3C—C3B—H3D	111.3
C6A—C5A—H5A	115.8	C16B—C4B—C1B	132.05 (9)
C7A—C6A—C11A	116.30 (9)	C16B—C4B—C3B	137.07 (9)
C7A—C6A—C5A	120.05 (9)	C1B—C4B—C3B	90.85 (7)
C11A—C6A—C5A	123.64 (8)	C2B—C5B—C6B	127.68 (9)
C8A—C7A—C6A	122.62 (9)	C2B—C5B—H5B	116.2
C8A—C7A—H7A	118.7	C6B—C5B—H5B	116.2
C6A—C7A—H7A	118.7	C7B—C6B—C11B	116.71 (8)
C7A—C8A—C9A	120.96 (9)	C7B—C6B—C5B	119.84 (8)
C7A—C8A—H8A	119.5	C11B—C6B—C5B	123.37 (8)
C9A—C8A—H8A	119.5	C8B—C7B—C6B	121.96 (9)
N1A—C9A—C8A	121.96 (9)	C8B—C7B—H7B	119.0
N1A—C9A—C10A	121.46 (9)	C6B—C7B—H7B	119.0
C8A—C9A—C10A	116.58 (9)	C7B—C8B—C9B	121.18 (8)
C11A—C10A—C9A	121.58 (9)	C7B—C8B—H8B	119.4
C11A—C10A—H10A	119.2	C9B—C8B—H8B	119.4
C9A—C10A—H10A	119.2	N1B—C9B—C8B	121.69 (8)
C10A—C11A—C6A	121.91 (9)	N1B—C9B—C10B	121.54 (8)
C10A—C11A—H11A	119.0	C8B—C9B—C10B	116.76 (8)
C6A—C11A—H11A	119.0	C11B—C10B—C9B	121.37 (9)
N1A—C12A—C13A	113.65 (9)	C11B—C10B—H10B	119.3
N1A—C12A—H12A	108.8	C9B—C10B—H10B	119.3
C13A—C12A—H12A	108.8	C10B—C11B—C6B	121.96 (9)
N1A—C12A—H12B	108.8	C10B—C11B—H11B	119.0
C13A—C12A—H12B	108.8	C6B—C11B—H11B	119.0
H12A—C12A—H12B	107.7	N1B—C12B—C13B	114.00 (8)
C12A—C13A—H13A	109.5	N1B—C12B—H12C	108.8
C12A—C13A—H13B	109.5	C13B—C12B—H12C	108.8
H13A—C13A—H13B	109.5	N1B—C12B—H12D	108.8
C12A—C13A—H13C	109.5	C13B—C12B—H12D	108.8
H13A—C13A—H13C	109.5	H12C—C12B—H12D	107.6
H13B—C13A—H13C	109.5	C12B—C13B—H13D	109.5
N1A—C12C—C13C	112.9 (12)	C12B—C13B—H13E	109.5
N1A—C12C—H12E	109.0	H13D—C13B—H13E	109.5
C13C—C12C—H12E	109.0	C12B—C13B—H13F	109.5
N1A—C12C—H12F	109.0	H13D—C13B—H13F	109.5
C13C—C12C—H12F	109.0	H13E—C13B—H13F	109.5
H12E—C12C—H12F	107.8	N1B—C14B—C15B	114.65 (9)
C12C—C13C—H13G	109.5	N1B—C14B—H14C	108.6
C12C—C13C—H13H	109.5	C15B—C14B—H14C	108.6
H13G—C13C—H13H	109.5	N1B—C14B—H14D	108.6
C12C—C13C—H13I	109.5	C15B—C14B—H14D	108.6
H13G—C13C—H13I	109.5	H14C—C14B—H14D	107.6
H13H—C13C—H13I	109.5	C14B—C15B—H15D	109.5
N1A—C14A—C15A	113.57 (9)	C14B—C15B—H15E	109.5
N1A—C14A—H14A	108.9	H15D—C15B—H15E	109.5
C15A—C14A—H14A	108.9	C14B—C15B—H15F	109.5
N1A—C14A—H14B	108.9	H15D—C15B—H15F	109.5
C15A—C14A—H14B	108.9	H15E—C15B—H15F	109.5
H14A—C14A—H14B	107.7	C4B—C16B—C17B	127.88 (9)
C14A—C15A—H15A	109.5	C4B—C16B—H16B	116.1
C14A—C15A—H15B	109.5	C17B—C16B—H16B	116.1
H15A—C15A—H15B	109.5	C22B—C17B—C18B	116.28 (8)
C14A—C15A—H15C	109.5	C22B—C17B—C16B	120.00 (8)
H15A—C15A—H15C	109.5	C18B—C17B—C16B	123.72 (9)
H15B—C15A—H15C	109.5	C19B—C18B—C17B	122.22 (9)
C4A—C16A—C17A	127.21 (9)	C19B—C18B—H18B	118.9
C4A—C16A—H16A	116.4	C17B—C18B—H18B	118.9
C17A—C16A—H16A	116.4	C18B—C19B—C20B	121.40 (9)
C22A—C17A—C18A	116.63 (8)	C18B—C19B—H19B	119.3
C22A—C17A—C16A	120.32 (8)	C20B—C19B—H19B	119.3
C18A—C17A—C16A	123.06 (8)	N2B—C20B—C21B	121.99 (9)
C19A—C18A—C17A	122.14 (9)	N2B—C20B—C19B	121.56 (9)
C19A—C18A—H18A	118.9	C21B—C20B—C19B	116.45 (8)
C17A—C18A—H18A	118.9	C22B—C21B—C20B	121.41 (9)
C18A—C19A—C20A	121.17 (9)	C22B—C21B—H21B	119.3
C18A—C19A—H19A	119.4	C20B—C21B—H21B	119.3
C20A—C19A—H19A	119.4	C21B—C22B—C17B	122.23 (9)
N2A—C20A—C19A	121.08 (9)	C21B—C22B—H22B	118.9
N2A—C20A—C21A	121.96 (8)	C17B—C22B—H22B	118.9
C19A—C20A—C21A	116.97 (8)	N2B—C23B—C24B	114.44 (9)
C22A—C21A—C20A	121.03 (9)	N2B—C23B—H23C	108.7
C22A—C21A—H21A	119.5	C24B—C23B—H23C	108.7
C20A—C21A—H21A	119.5	N2B—C23B—H23D	108.7
C21A—C22A—C17A	122.04 (9)	C24B—C23B—H23D	108.7
C21A—C22A—H22A	119.0	H23C—C23B—H23D	107.6
C17A—C22A—H22A	119.0	C23B—C24B—H24D	109.5
N2A—C23A—C24A	112.86 (8)	C23B—C24B—H24E	109.5
N2A—C23A—H23A	109.0	H24D—C24B—H24E	109.5
C24A—C23A—H23A	109.0	C23B—C24B—H24F	109.5
N2A—C23A—H23B	109.0	H24D—C24B—H24F	109.5
C24A—C23A—H23B	109.0	H24E—C24B—H24F	109.5
H23A—C23A—H23B	107.8	N2B—C25B—C26B	113.24 (9)
C23A—C24A—H24A	109.5	N2B—C25B—H25C	108.9
C23A—C24A—H24B	109.5	C26B—C25B—H25C	108.9
H24A—C24A—H24B	109.5	N2B—C25B—H25D	108.9
C23A—C24A—H24C	109.5	C26B—C25B—H25D	108.9
H24A—C24A—H24C	109.5	H25C—C25B—H25D	107.7
H24B—C24A—H24C	109.5	C25B—C26B—H26D	109.5
N2A—C25A—C26A	113.16 (9)	C25B—C26B—H26E	109.5
N2A—C25A—H25A	108.9	H26D—C26B—H26E	109.5
C26A—C25A—H25A	108.9	C25B—C26B—H26F	109.5
N2A—C25A—H25B	108.9	H26D—C26B—H26F	109.5
C26A—C25A—H25B	108.9	H26E—C26B—H26F	109.5
O1A—C1A—C2A—C5A	−1.18 (19)	C25A—N2A—C23A—C24A	−84.50 (11)
C4A—C1A—C2A—C5A	177.73 (10)	C20A—N2A—C25A—C26A	99.89 (11)
O1A—C1A—C2A—C3A	−179.37 (11)	C23A—N2A—C25A—C26A	−88.68 (11)
C4A—C1A—C2A—C3A	−0.46 (7)	O1B—C1B—C2B—C5B	−4.33 (19)
C5A—C2A—C3A—C4A	−177.58 (12)	C4B—C1B—C2B—C5B	174.51 (11)
C1A—C2A—C3A—C4A	0.44 (7)	O1B—C1B—C2B—C3B	179.78 (12)
O1A—C1A—C4A—C16A	−2.35 (19)	C4B—C1B—C2B—C3B	−1.38 (7)
C2A—C1A—C4A—C16A	178.75 (11)	C5B—C2B—C3B—C4B	−174.15 (12)
O1A—C1A—C4A—C3A	179.35 (11)	C1B—C2B—C3B—C4B	1.34 (7)
C2A—C1A—C4A—C3A	0.46 (7)	O1B—C1B—C4B—C16B	1.88 (19)
C2A—C3A—C4A—C16A	−178.60 (12)	C2B—C1B—C4B—C16B	−176.96 (11)
C2A—C3A—C4A—C1A	−0.45 (7)	O1B—C1B—C4B—C3B	−179.79 (12)
C1A—C2A—C5A—C6A	−178.32 (9)	C2B—C1B—C4B—C3B	1.38 (7)
C3A—C2A—C5A—C6A	−0.98 (18)	C2B—C3B—C4B—C16B	176.85 (12)
C2A—C5A—C6A—C7A	175.93 (10)	C2B—C3B—C4B—C1B	−1.34 (7)
C2A—C5A—C6A—C11A	−4.27 (16)	C1B—C2B—C5B—C6B	−173.25 (9)
C11A—C6A—C7A—C8A	−1.19 (15)	C3B—C2B—C5B—C6B	0.71 (18)
C5A—C6A—C7A—C8A	178.63 (10)	C2B—C5B—C6B—C7B	176.43 (9)
C6A—C7A—C8A—C9A	−0.31 (17)	C2B—C5B—C6B—C11B	−0.21 (15)
C14A—N1A—C9A—C8A	−176.73 (10)	C11B—C6B—C7B—C8B	1.66 (14)
C12A—N1A—C9A—C8A	10.59 (15)	C5B—C6B—C7B—C8B	−175.20 (9)
C12C—N1A—C9A—C8A	−32.1 (8)	C6B—C7B—C8B—C9B	0.59 (15)
C14A—N1A—C9A—C10A	3.67 (15)	C12B—N1B—C9B—C8B	−9.05 (13)
C12A—N1A—C9A—C10A	−169.01 (9)	C14B—N1B—C9B—C8B	−174.98 (9)
C12C—N1A—C9A—C10A	148.3 (8)	C12B—N1B—C9B—C10B	172.19 (9)
C7A—C8A—C9A—N1A	−177.60 (10)	C14B—N1B—C9B—C10B	6.27 (14)
C7A—C8A—C9A—C10A	2.02 (15)	C7B—C8B—C9B—N1B	179.00 (9)
N1A—C9A—C10A—C11A	177.33 (9)	C7B—C8B—C9B—C10B	−2.19 (14)
C8A—C9A—C10A—C11A	−2.29 (15)	N1B—C9B—C10B—C11B	−179.63 (9)
C9A—C10A—C11A—C6A	0.84 (15)	C8B—C9B—C10B—C11B	1.56 (14)
C7A—C6A—C11A—C10A	0.92 (14)	C9B—C10B—C11B—C6B	0.70 (15)
C5A—C6A—C11A—C10A	−178.89 (9)	C7B—C6B—C11B—C10B	−2.30 (14)
C9A—N1A—C12A—C13A	−92.37 (13)	C5B—C6B—C11B—C10B	174.44 (9)
C14A—N1A—C12A—C13A	94.73 (12)	C9B—N1B—C12B—C13B	−73.12 (12)
C12C—N1A—C12A—C13A	−7.2 (15)	C14B—N1B—C12B—C13B	93.36 (11)
C9A—N1A—C12C—C13C	102.8 (16)	C9B—N1B—C14B—C15B	76.85 (12)
C14A—N1A—C12C—C13C	−111.7 (16)	C12B—N1B—C14B—C15B	−89.53 (11)
C12A—N1A—C12C—C13C	−11.7 (10)	C1B—C4B—C16B—C17B	179.07 (10)
C9A—N1A—C14A—C15A	74.49 (12)	C3B—C4B—C16B—C17B	1.52 (19)
C12A—N1A—C14A—C15A	−112.55 (10)	C4B—C16B—C17B—C22B	177.18 (10)
C12C—N1A—C14A—C15A	−67.6 (8)	C4B—C16B—C17B—C18B	−2.18 (16)
C1A—C4A—C16A—C17A	179.89 (9)	C22B—C17B—C18B—C19B	0.15 (15)
C3A—C4A—C16A—C17A	−2.61 (18)	C16B—C17B—C18B—C19B	179.53 (9)
C4A—C16A—C17A—C22A	174.66 (9)	C17B—C18B—C19B—C20B	0.77 (16)
C4A—C16A—C17A—C18A	−4.74 (16)	C23B—N2B—C20B—C21B	−6.81 (14)
C22A—C17A—C18A—C19A	1.28 (15)	C25B—N2B—C20B—C21B	176.10 (9)
C16A—C17A—C18A—C19A	−179.30 (9)	C23B—N2B—C20B—C19B	174.08 (9)
C17A—C18A—C19A—C20A	−0.18 (16)	C25B—N2B—C20B—C19B	−3.01 (14)
C23A—N2A—C20A—C19A	174.36 (9)	C18B—C19B—C20B—N2B	177.67 (9)
C25A—N2A—C20A—C19A	−14.75 (14)	C18B—C19B—C20B—C21B	−1.49 (14)
C23A—N2A—C20A—C21A	−5.12 (14)	N2B—C20B—C21B—C22B	−177.79 (9)
C25A—N2A—C20A—C21A	165.76 (9)	C19B—C20B—C21B—C22B	1.37 (14)
C18A—C19A—C20A—N2A	179.01 (9)	C20B—C21B—C22B—C17B	−0.52 (15)
C18A—C19A—C20A—C21A	−1.48 (14)	C18B—C17B—C22B—C21B	−0.27 (14)
N2A—C20A—C21A—C22A	−178.46 (9)	C16B—C17B—C22B—C21B	−179.67 (9)
C19A—C20A—C21A—C22A	2.03 (14)	C20B—N2B—C23B—C24B	−80.11 (12)
C20A—C21A—C22A—C17A	−0.97 (15)	C25B—N2B—C23B—C24B	97.07 (11)
C18A—C17A—C22A—C21A	−0.71 (14)	C20B—N2B—C25B—C26B	86.23 (12)
C16A—C17A—C22A—C21A	179.85 (9)	C23B—N2B—C25B—C26B	−90.96 (11)
C20A—N2A—C23A—C24A	86.93 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C23A—H23A···O1B^i	0.99	2.56	3.5239 (14)	164

Symmetry code: (i) −x, −y+1, −z+1.

2,5-Bis[4-(diethylamino)benzylidene]cyclopentanone (II)

Crystal data

C27H34N2O	Z = 4
Mr = 402.56	F(000) = 872
Triclinic, P1	Dx = 1.188 Mg m^−3
a = 13.0640 (17) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.3132 (17) Å	Cell parameters from 9936 reflections
c = 14.9575 (19) Å	θ = 4.1–30.6°
α = 78.530 (1)°	µ = 0.07 mm^−1
β = 66.274 (2)°	T = 100 K
γ = 71.554 (2)°	Block, orange
V = 2251.5 (5) Å^3	0.30 × 0.30 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer	11331 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.018
φ and ω scans	θmax = 30.7°, θmin = 4.1°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −18→18
Tmin = 0.678, Tmax = 0.746	k = −19→19
26860 measured reflections	l = −21→21
13695 independent reflections

Refinement

Refinement on F^2	Primary atom site location: difference Fourier map
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.131	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0776P)^2 + 0.3784P] where P = (Fo^2 + 2Fc^2)/3
13695 reflections	(Δ/σ)max = 0.001
557 parameters	Δρmax = 0.53 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

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. The single crystal X-ray diffraction data were collected on a Bruker SMART APEX II diffractometer equipped with CCD area detector (λMoKa-radiation, graphite monochromator, φ- and ω-scan mode). The semi-empirical absorption correction was applied using the SADABS program (Bruker, 2016). The structures were determined by direct methods and refined by full-matrix least-square technique on F² in anisotropic approximation for non-hydrogen atoms.

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

	x	y	z	Uiso*/Ueq
O1A	0.51709 (8)	0.70816 (6)	0.12290 (7)	0.03267 (19)
N1A	−0.07851 (7)	0.76154 (7)	−0.00330 (6)	0.02241 (16)
N2A	0.88570 (7)	0.18375 (6)	0.39942 (6)	0.02112 (16)
C1A	0.49501 (9)	0.62289 (7)	0.12966 (7)	0.02048 (17)
C2A	0.40007 (8)	0.60815 (7)	0.10799 (6)	0.01796 (16)
C3A	0.40433 (8)	0.49149 (7)	0.12320 (7)	0.01804 (16)
H3A	0.4133	0.4658	0.0620	0.020 (3)*
H3B	0.3322	0.4792	0.1755	0.024 (3)*
C4A	0.51082 (8)	0.43261 (7)	0.15318 (7)	0.01907 (17)
H4A	0.4870	0.3897	0.2165	0.029 (3)*
H4B	0.5700	0.3849	0.1027	0.027 (3)*
C5A	0.55834 (8)	0.51811 (7)	0.16201 (7)	0.01868 (16)
C6A	0.32593 (8)	0.69435 (7)	0.08172 (7)	0.01849 (16)
H6A	0.3422	0.7598	0.0791	0.022*
C7A	0.22654 (8)	0.70505 (7)	0.05696 (6)	0.01736 (16)
C8A	0.16379 (8)	0.80816 (7)	0.03576 (7)	0.01934 (17)
H8A	0.1898	0.8668	0.0368	0.023*
C9A	0.06612 (8)	0.82774 (7)	0.01356 (7)	0.02010 (17)
H9A	0.0271	0.8988	−0.0006	0.024*
C10A	0.02334 (8)	0.74334 (7)	0.01157 (6)	0.01862 (17)
C11A	0.08916 (8)	0.63928 (7)	0.02824 (7)	0.02170 (18)
H11A	0.0660	0.5803	0.0234	0.026*
C12A	0.18623 (8)	0.62108 (7)	0.05131 (7)	0.02013 (17)
H12A	0.2268	0.5500	0.0637	0.024*
C13A	−0.13990 (8)	0.86945 (8)	−0.02735 (7)	0.02230 (18)
H13A	−0.1428	0.9174	0.0170	0.027*
H13B	−0.2207	0.8707	−0.0149	0.027*
C14A	−0.08520 (9)	0.91214 (8)	−0.13290 (7)	0.02320 (18)
H14A	−0.0911	0.8709	−0.1772	0.035*
H14B	−0.0034	0.9061	−0.1476	0.035*
H14C	−0.1259	0.9869	−0.1418	0.035*
C15A	−0.11625 (10)	0.67443 (9)	−0.01579 (9)	0.0291 (2)
H15A	−0.2005	0.6989	−0.0026	0.035*
H15B	−0.1037	0.6149	0.0334	0.035*
C16A	−0.05378 (12)	0.63385 (9)	−0.11711 (9)	0.0355 (3)
H16A	−0.0662	0.6921	−0.1664	0.053*
H16B	−0.0842	0.5768	−0.1206	0.053*
H16C	0.0294	0.6065	−0.1298	0.053*
C17A	0.63670 (8)	0.51472 (7)	0.20090 (7)	0.02018 (17)
H17A	0.6504	0.5814	0.1983	0.024*
C18A	0.70342 (8)	0.42644 (7)	0.24595 (7)	0.01826 (16)
C19A	0.72862 (8)	0.31857 (7)	0.23204 (7)	0.01858 (16)
H19A	0.7033	0.2998	0.1879	0.022*
C20A	0.78939 (8)	0.23917 (7)	0.28101 (7)	0.01814 (16)
H20A	0.8054	0.1673	0.2691	0.022*
C21A	0.82833 (8)	0.26228 (7)	0.34845 (6)	0.01713 (16)
C22A	0.80523 (8)	0.37081 (7)	0.36095 (7)	0.02036 (17)
H22A	0.8311	0.3900	0.4045	0.024*
C23A	0.74557 (8)	0.44920 (7)	0.31062 (7)	0.02090 (18)
H23A	0.7325	0.5214	0.3200	0.025*
C24A	0.91651 (9)	0.20945 (8)	0.47409 (7)	0.02219 (18)
H24A	0.9200	0.1479	0.5234	0.027*
H24B	0.8550	0.2702	0.5079	0.027*
C25A	1.03176 (10)	0.23733 (10)	0.43249 (9)	0.0303 (2)
H25A	1.0290	0.2982	0.3835	0.045*
H25B	1.0937	0.1763	0.4016	0.045*
H25C	1.0471	0.2555	0.4854	0.045*
C26A	0.91629 (8)	0.07116 (7)	0.38542 (7)	0.01964 (17)
H26A	0.9879	0.0346	0.3991	0.024*
H26B	0.9330	0.0636	0.3160	0.024*
C27A	0.82189 (10)	0.01700 (8)	0.45043 (8)	0.0274 (2)
H27A	0.7531	0.0480	0.4328	0.041*
H27B	0.8019	0.0272	0.5191	0.041*
H27C	0.8497	−0.0591	0.4413	0.041*
O1B	0.05811 (6)	0.85510 (5)	0.27787 (6)	0.02336 (14)
N1B	−0.54350 (7)	1.03535 (6)	0.12908 (6)	0.02018 (15)
N2B	0.41242 (7)	0.26192 (7)	0.48397 (7)	0.02379 (17)
C1B	0.01588 (8)	0.78178 (7)	0.28490 (6)	0.01733 (16)
C2B	−0.09170 (7)	0.79209 (7)	0.26869 (6)	0.01683 (16)
C3B	−0.11411 (8)	0.68429 (7)	0.28519 (7)	0.01901 (17)
H3C	−0.1116	0.6640	0.2240	0.027 (3)*
H3D	−0.1912	0.6848	0.3366	0.024 (3)*
C4B	−0.01664 (8)	0.60496 (7)	0.31804 (7)	0.02060 (17)
H4C	−0.0500	0.5732	0.3855	0.028 (3)*
H4D	0.0265	0.5471	0.2736	0.032 (3)*
C5B	0.06242 (8)	0.66877 (7)	0.31372 (6)	0.01739 (16)
C6B	−0.14947 (8)	0.88877 (7)	0.24049 (6)	0.01745 (16)
H6B	−0.1164	0.9446	0.2358	0.021*
C7B	−0.25247 (7)	0.92248 (7)	0.21612 (6)	0.01683 (16)
C8B	−0.28979 (8)	1.02974 (7)	0.18385 (7)	0.01861 (17)
H8B	−0.2479	1.0777	0.1812	0.022*
C9B	−0.38481 (8)	1.06818 (7)	0.15588 (7)	0.01913 (17)
H9B	−0.4066	1.1413	0.1347	0.023*
C10B	−0.44996 (8)	0.99998 (7)	0.15833 (6)	0.01727 (16)
C11B	−0.41324 (8)	0.89176 (7)	0.19098 (7)	0.01880 (17)
H11B	−0.4552	0.8436	0.1941	0.023*
C12B	−0.31768 (8)	0.85503 (7)	0.21830 (7)	0.01832 (16)
H12B	−0.2953	0.7820	0.2392	0.022*
C13B	−0.57473 (9)	1.14338 (8)	0.08611 (8)	0.02440 (19)
H13C	−0.6100	1.1429	0.0388	0.029*
H13D	−0.5030	1.1668	0.0490	0.029*
C14B	−0.65832 (11)	1.22414 (9)	0.15934 (10)	0.0366 (3)
H14D	−0.6749	1.2942	0.1244	0.055*
H14E	−0.6234	1.2273	0.2054	0.055*
H14F	−0.7306	1.2029	0.1955	0.055*
C15B	−0.62048 (8)	0.96795 (8)	0.14737 (7)	0.02168 (18)
H15C	−0.5726	0.8965	0.1261	0.026*
H15D	−0.6688	0.9982	0.1067	0.026*
C16B	−0.70002 (9)	0.95615 (9)	0.25423 (8)	0.0295 (2)
H16D	−0.7492	0.9107	0.2606	0.044*
H16E	−0.7489	1.0263	0.2758	0.044*
H16F	−0.6531	0.9238	0.2949	0.044*
C17B	0.16086 (8)	0.64092 (7)	0.33271 (6)	0.01794 (16)
H17B	0.1964	0.6971	0.3199	0.022*
C18B	0.22223 (8)	0.54095 (7)	0.36910 (7)	0.01803 (16)
C19B	0.18877 (8)	0.44560 (8)	0.39326 (8)	0.02249 (18)
H19B	0.1213	0.4440	0.3844	0.027*
C20B	0.25142 (8)	0.35389 (8)	0.42957 (8)	0.02345 (19)
H20B	0.2266	0.2907	0.4440	0.028*
C21B	0.35163 (8)	0.35223 (7)	0.44562 (7)	0.01980 (17)
C22B	0.38554 (8)	0.44784 (8)	0.42128 (7)	0.02123 (18)
H22B	0.4523	0.4502	0.4309	0.025*
C23B	0.32292 (8)	0.53793 (7)	0.38373 (7)	0.02021 (17)
H23B	0.3490	0.6006	0.3671	0.024*
C24B	0.52849 (8)	0.25395 (9)	0.47975 (8)	0.0282 (2)
H24C	0.5643	0.3011	0.4235	0.034*
H24D	0.5766	0.1802	0.4678	0.034*
C25B	0.52990 (12)	0.28331 (12)	0.57187 (10)	0.0413 (3)
H25D	0.6102	0.2726	0.5654	0.062*
H25E	0.4927	0.2383	0.6283	0.062*
H25F	0.4876	0.3580	0.5815	0.062*
C26B	0.38001 (8)	0.16196 (8)	0.50572 (7)	0.02336 (19)
H26C	0.2945	0.1771	0.5344	0.028*
H26D	0.4107	0.1171	0.5553	0.028*
C27B	0.42497 (10)	0.10025 (9)	0.41592 (9)	0.0321 (2)
H27D	0.3906	0.1420	0.3683	0.048*
H27E	0.4037	0.0327	0.4356	0.048*
H27F	0.5095	0.0864	0.3861	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0446 (5)	0.0157 (3)	0.0539 (5)	−0.0104 (3)	−0.0364 (4)	0.0059 (3)
N1A	0.0211 (4)	0.0194 (4)	0.0280 (4)	−0.0041 (3)	−0.0134 (3)	0.0030 (3)
N2A	0.0295 (4)	0.0154 (3)	0.0241 (4)	−0.0033 (3)	−0.0179 (3)	−0.0002 (3)
C1A	0.0268 (4)	0.0151 (4)	0.0244 (4)	−0.0049 (3)	−0.0161 (4)	0.0016 (3)
C2A	0.0223 (4)	0.0152 (4)	0.0187 (4)	−0.0052 (3)	−0.0101 (3)	−0.0004 (3)
C3A	0.0217 (4)	0.0145 (4)	0.0199 (4)	−0.0047 (3)	−0.0099 (3)	−0.0007 (3)
C4A	0.0254 (4)	0.0135 (4)	0.0208 (4)	−0.0033 (3)	−0.0128 (3)	−0.0003 (3)
C5A	0.0233 (4)	0.0143 (4)	0.0198 (4)	−0.0037 (3)	−0.0112 (3)	0.0008 (3)
C6A	0.0228 (4)	0.0154 (4)	0.0194 (4)	−0.0051 (3)	−0.0103 (3)	−0.0003 (3)
C7A	0.0197 (4)	0.0153 (4)	0.0169 (4)	−0.0033 (3)	−0.0080 (3)	−0.0002 (3)
C8A	0.0242 (4)	0.0142 (4)	0.0207 (4)	−0.0037 (3)	−0.0103 (3)	−0.0014 (3)
C9A	0.0229 (4)	0.0147 (4)	0.0218 (4)	−0.0011 (3)	−0.0102 (3)	−0.0014 (3)
C10A	0.0189 (4)	0.0182 (4)	0.0177 (4)	−0.0038 (3)	−0.0075 (3)	0.0009 (3)
C11A	0.0243 (4)	0.0157 (4)	0.0284 (5)	−0.0064 (3)	−0.0144 (4)	0.0030 (3)
C12A	0.0231 (4)	0.0139 (4)	0.0252 (4)	−0.0041 (3)	−0.0130 (4)	0.0022 (3)
C13A	0.0184 (4)	0.0226 (4)	0.0216 (4)	−0.0006 (3)	−0.0081 (3)	0.0015 (3)
C14A	0.0244 (4)	0.0219 (4)	0.0216 (4)	−0.0046 (3)	−0.0094 (4)	0.0017 (3)
C15A	0.0288 (5)	0.0258 (5)	0.0397 (6)	−0.0117 (4)	−0.0209 (5)	0.0078 (4)
C16A	0.0488 (7)	0.0249 (5)	0.0415 (6)	−0.0128 (5)	−0.0257 (6)	0.0034 (4)
C17A	0.0243 (4)	0.0152 (4)	0.0232 (4)	−0.0042 (3)	−0.0126 (3)	0.0004 (3)
C18A	0.0206 (4)	0.0156 (4)	0.0205 (4)	−0.0039 (3)	−0.0108 (3)	0.0000 (3)
C19A	0.0226 (4)	0.0168 (4)	0.0192 (4)	−0.0040 (3)	−0.0114 (3)	−0.0016 (3)
C20A	0.0217 (4)	0.0147 (4)	0.0195 (4)	−0.0029 (3)	−0.0099 (3)	−0.0025 (3)
C21A	0.0184 (4)	0.0160 (4)	0.0177 (4)	−0.0032 (3)	−0.0087 (3)	−0.0005 (3)
C22A	0.0245 (4)	0.0173 (4)	0.0241 (4)	−0.0035 (3)	−0.0146 (4)	−0.0031 (3)
C23A	0.0246 (4)	0.0154 (4)	0.0268 (4)	−0.0037 (3)	−0.0144 (4)	−0.0023 (3)
C24A	0.0273 (4)	0.0219 (4)	0.0220 (4)	−0.0045 (3)	−0.0156 (4)	−0.0008 (3)
C25A	0.0281 (5)	0.0347 (6)	0.0341 (5)	−0.0083 (4)	−0.0172 (4)	−0.0035 (4)
C26A	0.0227 (4)	0.0149 (4)	0.0211 (4)	−0.0023 (3)	−0.0103 (3)	−0.0002 (3)
C27A	0.0304 (5)	0.0216 (4)	0.0262 (5)	−0.0079 (4)	−0.0071 (4)	0.0015 (4)
O1B	0.0239 (3)	0.0177 (3)	0.0337 (4)	−0.0067 (3)	−0.0155 (3)	−0.0005 (3)
N1B	0.0194 (3)	0.0184 (4)	0.0257 (4)	−0.0056 (3)	−0.0128 (3)	0.0025 (3)
N2B	0.0178 (4)	0.0199 (4)	0.0324 (4)	−0.0032 (3)	−0.0119 (3)	0.0034 (3)
C1B	0.0181 (4)	0.0167 (4)	0.0181 (4)	−0.0039 (3)	−0.0079 (3)	−0.0019 (3)
C2B	0.0167 (4)	0.0176 (4)	0.0174 (4)	−0.0053 (3)	−0.0068 (3)	−0.0015 (3)
C3B	0.0198 (4)	0.0166 (4)	0.0229 (4)	−0.0056 (3)	−0.0100 (3)	−0.0003 (3)
C4B	0.0213 (4)	0.0167 (4)	0.0260 (4)	−0.0055 (3)	−0.0113 (3)	0.0003 (3)
C5B	0.0189 (4)	0.0151 (4)	0.0180 (4)	−0.0031 (3)	−0.0074 (3)	−0.0019 (3)
C6B	0.0181 (4)	0.0176 (4)	0.0185 (4)	−0.0058 (3)	−0.0079 (3)	−0.0008 (3)
C7B	0.0170 (4)	0.0174 (4)	0.0171 (4)	−0.0047 (3)	−0.0073 (3)	−0.0012 (3)
C8B	0.0199 (4)	0.0172 (4)	0.0211 (4)	−0.0061 (3)	−0.0091 (3)	−0.0014 (3)
C9B	0.0202 (4)	0.0162 (4)	0.0225 (4)	−0.0044 (3)	−0.0100 (3)	−0.0006 (3)
C10B	0.0168 (4)	0.0182 (4)	0.0173 (4)	−0.0043 (3)	−0.0069 (3)	−0.0015 (3)
C11B	0.0183 (4)	0.0175 (4)	0.0229 (4)	−0.0062 (3)	−0.0092 (3)	−0.0005 (3)
C12B	0.0184 (4)	0.0160 (4)	0.0216 (4)	−0.0050 (3)	−0.0091 (3)	0.0008 (3)
C13B	0.0261 (5)	0.0216 (4)	0.0296 (5)	−0.0081 (4)	−0.0169 (4)	0.0066 (4)
C14B	0.0339 (6)	0.0206 (5)	0.0521 (7)	−0.0017 (4)	−0.0174 (5)	−0.0015 (5)
C15B	0.0200 (4)	0.0209 (4)	0.0282 (5)	−0.0063 (3)	−0.0132 (4)	0.0000 (3)
C16B	0.0231 (5)	0.0310 (5)	0.0328 (5)	−0.0100 (4)	−0.0093 (4)	0.0038 (4)
C17B	0.0189 (4)	0.0170 (4)	0.0180 (4)	−0.0036 (3)	−0.0072 (3)	−0.0023 (3)
C18B	0.0174 (4)	0.0174 (4)	0.0190 (4)	−0.0025 (3)	−0.0073 (3)	−0.0028 (3)
C19B	0.0202 (4)	0.0200 (4)	0.0301 (5)	−0.0047 (3)	−0.0132 (4)	−0.0001 (3)
C20B	0.0213 (4)	0.0179 (4)	0.0328 (5)	−0.0055 (3)	−0.0131 (4)	0.0018 (4)
C21B	0.0165 (4)	0.0190 (4)	0.0210 (4)	−0.0022 (3)	−0.0064 (3)	−0.0006 (3)
C22B	0.0165 (4)	0.0221 (4)	0.0257 (4)	−0.0048 (3)	−0.0095 (3)	0.0000 (3)
C23B	0.0185 (4)	0.0192 (4)	0.0234 (4)	−0.0048 (3)	−0.0085 (3)	−0.0012 (3)
C24B	0.0166 (4)	0.0261 (5)	0.0379 (6)	−0.0037 (4)	−0.0113 (4)	0.0061 (4)
C25B	0.0357 (6)	0.0558 (8)	0.0419 (7)	−0.0236 (6)	−0.0228 (5)	0.0128 (6)
C26B	0.0209 (4)	0.0195 (4)	0.0256 (4)	−0.0040 (3)	−0.0078 (4)	0.0033 (3)
C27B	0.0343 (6)	0.0246 (5)	0.0312 (5)	−0.0039 (4)	−0.0088 (4)	−0.0022 (4)

Geometric parameters (Å, º)

O1A—C1A	1.2330 (12)	O1B—C1B	1.2335 (11)
N1A—C10A	1.3752 (12)	N1B—C10B	1.3749 (11)
N1A—C13A	1.4608 (12)	N1B—C13B	1.4561 (12)
N1A—C15A	1.4646 (13)	N1B—C15B	1.4641 (12)
N2A—C21A	1.3722 (11)	N2B—C21B	1.3760 (12)
N2A—C24A	1.4585 (12)	N2B—C26B	1.4593 (13)
N2A—C26A	1.4590 (12)	N2B—C24B	1.4623 (13)
C1A—C2A	1.4780 (13)	C1B—C2B	1.4804 (12)
C1A—C5A	1.4792 (12)	C1B—C5B	1.4810 (12)
C2A—C6A	1.3539 (12)	C2B—C6B	1.3527 (12)
C2A—C3A	1.5106 (12)	C2B—C3B	1.5077 (12)
C3A—C4A	1.5566 (13)	C3B—C4B	1.5569 (13)
C3A—H3A	0.9900	C3B—H3C	0.9900
C3A—H3B	0.9900	C3B—H3D	0.9900
C4A—C5A	1.5071 (13)	C4B—C5B	1.5074 (13)
C4A—H4A	0.9900	C4B—H4C	0.9900
C4A—H4B	0.9900	C4B—H4D	0.9900
C5A—C17A	1.3520 (13)	C5B—C17B	1.3499 (12)
C6A—C7A	1.4464 (12)	C6B—C7B	1.4465 (12)
C6A—H6A	0.9500	C6B—H6B	0.9500
C7A—C12A	1.4072 (13)	C7B—C12B	1.4083 (12)
C7A—C8A	1.4075 (12)	C7B—C8B	1.4087 (12)
C8A—C9A	1.3793 (13)	C8B—C9B	1.3816 (12)
C8A—H8A	0.9500	C8B—H8B	0.9500
C9A—C10A	1.4141 (13)	C9B—C10B	1.4145 (12)
C9A—H9A	0.9500	C9B—H9B	0.9500
C10A—C11A	1.4150 (12)	C10B—C11B	1.4198 (12)
C11A—C12A	1.3821 (13)	C11B—C12B	1.3819 (12)
C11A—H11A	0.9500	C11B—H11B	0.9500
C12A—H12A	0.9500	C12B—H12B	0.9500
C13A—C14A	1.5227 (14)	C13B—C14B	1.5202 (16)
C13A—H13A	0.9900	C13B—H13C	0.9900
C13A—H13B	0.9900	C13B—H13D	0.9900
C14A—H14A	0.9800	C14B—H14D	0.9800
C14A—H14B	0.9800	C14B—H14E	0.9800
C14A—H14C	0.9800	C14B—H14F	0.9800
C15A—C16A	1.5186 (18)	C15B—C16B	1.5251 (15)
C15A—H15A	0.9900	C15B—H15C	0.9900
C15A—H15B	0.9900	C15B—H15D	0.9900
C16A—H16A	0.9800	C16B—H16D	0.9800
C16A—H16B	0.9800	C16B—H16E	0.9800
C16A—H16C	0.9800	C16B—H16F	0.9800
C17A—C18A	1.4507 (12)	C17B—C18B	1.4485 (12)
C17A—H17A	0.9500	C17B—H17B	0.9500
C18A—C19A	1.4066 (12)	C18B—C23B	1.4050 (12)
C18A—C23A	1.4077 (12)	C18B—C19B	1.4053 (13)
C19A—C20A	1.3831 (12)	C19B—C20B	1.3846 (13)
C19A—H19A	0.9500	C19B—H19B	0.9500
C20A—C21A	1.4164 (12)	C20B—C21B	1.4158 (13)
C20A—H20A	0.9500	C20B—H20B	0.9500
C21A—C22A	1.4141 (12)	C21B—C22B	1.4113 (13)
C22A—C23A	1.3815 (12)	C22B—C23B	1.3799 (13)
C22A—H22A	0.9500	C22B—H22B	0.9500
C23A—H23A	0.9500	C23B—H23B	0.9500
C24A—C25A	1.5165 (15)	C24B—C25B	1.5136 (18)
C24A—H24A	0.9900	C24B—H24C	0.9900
C24A—H24B	0.9900	C24B—H24D	0.9900
C25A—H25A	0.9800	C25B—H25D	0.9800
C25A—H25B	0.9800	C25B—H25E	0.9800
C25A—H25C	0.9800	C25B—H25F	0.9800
C26A—C27A	1.5183 (14)	C26B—C27B	1.5241 (15)
C26A—H26A	0.9900	C26B—H26C	0.9900
C26A—H26B	0.9900	C26B—H26D	0.9900
C27A—H27A	0.9800	C27B—H27D	0.9800
C27A—H27B	0.9800	C27B—H27E	0.9800
C27A—H27C	0.9800	C27B—H27F	0.9800
C10A—N1A—C13A	120.26 (8)	C10B—N1B—C13B	121.39 (8)
C10A—N1A—C15A	121.54 (8)	C10B—N1B—C15B	120.77 (8)
C13A—N1A—C15A	117.02 (8)	C13B—N1B—C15B	117.67 (7)
C21A—N2A—C24A	120.75 (8)	C21B—N2B—C26B	121.66 (8)
C21A—N2A—C26A	123.16 (8)	C21B—N2B—C24B	120.62 (8)
C24A—N2A—C26A	116.06 (7)	C26B—N2B—C24B	115.73 (8)
O1A—C1A—C2A	125.86 (8)	O1B—C1B—C2B	125.88 (8)
O1A—C1A—C5A	125.69 (9)	O1B—C1B—C5B	125.79 (8)
C2A—C1A—C5A	108.45 (8)	C2B—C1B—C5B	108.31 (7)
C6A—C2A—C1A	119.23 (8)	C6B—C2B—C1B	119.07 (8)
C6A—C2A—C3A	131.44 (8)	C6B—C2B—C3B	131.39 (8)
C1A—C2A—C3A	109.31 (7)	C1B—C2B—C3B	109.50 (7)
C2A—C3A—C4A	106.38 (7)	C2B—C3B—C4B	106.34 (7)
C2A—C3A—H3A	110.5	C2B—C3B—H3C	110.5
C4A—C3A—H3A	110.5	C4B—C3B—H3C	110.5
C2A—C3A—H3B	110.5	C2B—C3B—H3D	110.5
C4A—C3A—H3B	110.5	C4B—C3B—H3D	110.5
H3A—C3A—H3B	108.6	H3C—C3B—H3D	108.7
C5A—C4A—C3A	105.95 (7)	C5B—C4B—C3B	106.10 (7)
C5A—C4A—H4A	110.5	C5B—C4B—H4C	110.5
C3A—C4A—H4A	110.5	C3B—C4B—H4C	110.5
C5A—C4A—H4B	110.5	C5B—C4B—H4D	110.5
C3A—C4A—H4B	110.5	C3B—C4B—H4D	110.5
H4A—C4A—H4B	108.7	H4C—C4B—H4D	108.7
C17A—C5A—C1A	118.52 (8)	C17B—C5B—C1B	118.52 (8)
C17A—C5A—C4A	131.54 (8)	C17B—C5B—C4B	131.82 (8)
C1A—C5A—C4A	109.62 (8)	C1B—C5B—C4B	109.65 (7)
C2A—C6A—C7A	131.80 (8)	C2B—C6B—C7B	131.64 (8)
C2A—C6A—H6A	114.1	C2B—C6B—H6B	114.2
C7A—C6A—H6A	114.1	C7B—C6B—H6B	114.2
C12A—C7A—C8A	116.13 (8)	C12B—C7B—C8B	116.16 (8)
C12A—C7A—C6A	125.92 (8)	C12B—C7B—C6B	124.98 (8)
C8A—C7A—C6A	117.95 (8)	C8B—C7B—C6B	118.81 (8)
C9A—C8A—C7A	122.83 (8)	C9B—C8B—C7B	122.77 (8)
C9A—C8A—H8A	118.6	C9B—C8B—H8B	118.6
C7A—C8A—H8A	118.6	C7B—C8B—H8B	118.6
C8A—C9A—C10A	120.86 (8)	C8B—C9B—C10B	120.77 (8)
C8A—C9A—H9A	119.6	C8B—C9B—H9B	119.6
C10A—C9A—H9A	119.6	C10B—C9B—H9B	119.6
N1A—C10A—C9A	121.72 (8)	N1B—C10B—C9B	122.15 (8)
N1A—C10A—C11A	121.72 (8)	N1B—C10B—C11B	120.92 (8)
C9A—C10A—C11A	116.54 (8)	C9B—C10B—C11B	116.92 (8)
C12A—C11A—C10A	121.78 (9)	C12B—C11B—C10B	121.30 (8)
C12A—C11A—H11A	119.1	C12B—C11B—H11B	119.4
C10A—C11A—H11A	119.1	C10B—C11B—H11B	119.4
C11A—C12A—C7A	121.74 (8)	C11B—C12B—C7B	122.09 (8)
C11A—C12A—H12A	119.1	C11B—C12B—H12B	119.0
C7A—C12A—H12A	119.1	C7B—C12B—H12B	119.0
N1A—C13A—C14A	114.04 (8)	N1B—C13B—C14B	114.86 (9)
N1A—C13A—H13A	108.7	N1B—C13B—H13C	108.6
C14A—C13A—H13A	108.7	C14B—C13B—H13C	108.6
N1A—C13A—H13B	108.7	N1B—C13B—H13D	108.6
C14A—C13A—H13B	108.7	C14B—C13B—H13D	108.6
H13A—C13A—H13B	107.6	H13C—C13B—H13D	107.5
C13A—C14A—H14A	109.5	C13B—C14B—H14D	109.5
C13A—C14A—H14B	109.5	C13B—C14B—H14E	109.5
H14A—C14A—H14B	109.5	H14D—C14B—H14E	109.5
C13A—C14A—H14C	109.5	C13B—C14B—H14F	109.5
H14A—C14A—H14C	109.5	H14D—C14B—H14F	109.5
H14B—C14A—H14C	109.5	H14E—C14B—H14F	109.5
N1A—C15A—C16A	113.90 (9)	N1B—C15B—C16B	114.15 (8)
N1A—C15A—H15A	108.8	N1B—C15B—H15C	108.7
C16A—C15A—H15A	108.8	C16B—C15B—H15C	108.7
N1A—C15A—H15B	108.8	N1B—C15B—H15D	108.7
C16A—C15A—H15B	108.8	C16B—C15B—H15D	108.7
H15A—C15A—H15B	107.7	H15C—C15B—H15D	107.6
C15A—C16A—H16A	109.5	C15B—C16B—H16D	109.5
C15A—C16A—H16B	109.5	C15B—C16B—H16E	109.5
H16A—C16A—H16B	109.5	H16D—C16B—H16E	109.5
C15A—C16A—H16C	109.5	C15B—C16B—H16F	109.5
H16A—C16A—H16C	109.5	H16D—C16B—H16F	109.5
H16B—C16A—H16C	109.5	H16E—C16B—H16F	109.5
C5A—C17A—C18A	130.88 (9)	C5B—C17B—C18B	131.73 (9)
C5A—C17A—H17A	114.6	C5B—C17B—H17B	114.1
C18A—C17A—H17A	114.6	C18B—C17B—H17B	114.1
C19A—C18A—C23A	116.40 (8)	C23B—C18B—C19B	116.24 (8)
C19A—C18A—C17A	125.63 (8)	C23B—C18B—C17B	118.13 (8)
C23A—C18A—C17A	117.96 (8)	C19B—C18B—C17B	125.62 (8)
C20A—C19A—C18A	121.66 (8)	C20B—C19B—C18B	121.86 (9)
C20A—C19A—H19A	119.2	C20B—C19B—H19B	119.1
C18A—C19A—H19A	119.2	C18B—C19B—H19B	119.1
C19A—C20A—C21A	121.71 (8)	C19B—C20B—C21B	121.42 (9)
C19A—C20A—H20A	119.1	C19B—C20B—H20B	119.3
C21A—C20A—H20A	119.1	C21B—C20B—H20B	119.3
N2A—C21A—C22A	121.29 (8)	N2B—C21B—C22B	121.61 (8)
N2A—C21A—C20A	122.02 (8)	N2B—C21B—C20B	121.55 (9)
C22A—C21A—C20A	116.69 (8)	C22B—C21B—C20B	116.84 (8)
C23A—C22A—C21A	120.85 (8)	C23B—C22B—C21B	120.83 (9)
C23A—C22A—H22A	119.6	C23B—C22B—H22B	119.6
C21A—C22A—H22A	119.6	C21B—C22B—H22B	119.6
C22A—C23A—C18A	122.63 (9)	C22B—C23B—C18B	122.80 (9)
C22A—C23A—H23A	118.7	C22B—C23B—H23B	118.6
C18A—C23A—H23A	118.7	C18B—C23B—H23B	118.6
N2A—C24A—C25A	113.00 (9)	N2B—C24B—C25B	113.79 (9)
N2A—C24A—H24A	109.0	N2B—C24B—H24C	108.8
C25A—C24A—H24A	109.0	C25B—C24B—H24C	108.8
N2A—C24A—H24B	109.0	N2B—C24B—H24D	108.8
C25A—C24A—H24B	109.0	C25B—C24B—H24D	108.8
H24A—C24A—H24B	107.8	H24C—C24B—H24D	107.7
C24A—C25A—H25A	109.5	C24B—C25B—H25D	109.5
C24A—C25A—H25B	109.5	C24B—C25B—H25E	109.5
H25A—C25A—H25B	109.5	H25D—C25B—H25E	109.5
C24A—C25A—H25C	109.5	C24B—C25B—H25F	109.5
H25A—C25A—H25C	109.5	H25D—C25B—H25F	109.5
H25B—C25A—H25C	109.5	H25E—C25B—H25F	109.5
N2A—C26A—C27A	113.37 (8)	N2B—C26B—C27B	113.26 (9)
N2A—C26A—H26A	108.9	N2B—C26B—H26C	108.9
C27A—C26A—H26A	108.9	C27B—C26B—H26C	108.9
N2A—C26A—H26B	108.9	N2B—C26B—H26D	108.9
C27A—C26A—H26B	108.9	C27B—C26B—H26D	108.9
H26A—C26A—H26B	107.7	H26C—C26B—H26D	107.7
C26A—C27A—H27A	109.5	C26B—C27B—H27D	109.5
C26A—C27A—H27B	109.5	C26B—C27B—H27E	109.5
H27A—C27A—H27B	109.5	H27D—C27B—H27E	109.5
C26A—C27A—H27C	109.5	C26B—C27B—H27F	109.5
H27A—C27A—H27C	109.5	H27D—C27B—H27F	109.5
H27B—C27A—H27C	109.5	H27E—C27B—H27F	109.5
O1A—C1A—C2A—C6A	−2.73 (15)	O1B—C1B—C2B—C6B	2.29 (14)
C5A—C1A—C2A—C6A	176.61 (8)	C5B—C1B—C2B—C6B	−179.27 (8)
O1A—C1A—C2A—C3A	178.73 (10)	O1B—C1B—C2B—C3B	−179.57 (9)
C5A—C1A—C2A—C3A	−1.93 (10)	C5B—C1B—C2B—C3B	−1.13 (10)
C6A—C2A—C3A—C4A	−179.90 (9)	C6B—C2B—C3B—C4B	−179.49 (9)
C1A—C2A—C3A—C4A	−1.59 (10)	C1B—C2B—C3B—C4B	2.68 (10)
C2A—C3A—C4A—C5A	4.40 (9)	C2B—C3B—C4B—C5B	−3.16 (10)
O1A—C1A—C5A—C17A	9.99 (15)	O1B—C1B—C5B—C17B	−1.28 (14)
C2A—C1A—C5A—C17A	−169.35 (9)	C2B—C1B—C5B—C17B	−179.72 (8)
O1A—C1A—C5A—C4A	−175.81 (10)	O1B—C1B—C5B—C4B	177.48 (9)
C2A—C1A—C5A—C4A	4.85 (10)	C2B—C1B—C5B—C4B	−0.96 (10)
C3A—C4A—C5A—C17A	167.49 (10)	C3B—C4B—C5B—C17B	−178.89 (9)
C3A—C4A—C5A—C1A	−5.71 (10)	C3B—C4B—C5B—C1B	2.57 (10)
C1A—C2A—C6A—C7A	−179.72 (9)	C1B—C2B—C6B—C7B	177.49 (9)
C3A—C2A—C6A—C7A	−1.55 (17)	C3B—C2B—C6B—C7B	−0.17 (17)
C2A—C6A—C7A—C12A	−2.67 (16)	C2B—C6B—C7B—C12B	0.62 (16)
C2A—C6A—C7A—C8A	177.77 (9)	C2B—C6B—C7B—C8B	−176.75 (9)
C12A—C7A—C8A—C9A	1.97 (13)	C12B—C7B—C8B—C9B	0.15 (13)
C6A—C7A—C8A—C9A	−178.43 (8)	C6B—C7B—C8B—C9B	177.76 (8)
C7A—C8A—C9A—C10A	0.34 (14)	C7B—C8B—C9B—C10B	−0.11 (14)
C13A—N1A—C10A—C9A	6.16 (13)	C13B—N1B—C10B—C9B	5.22 (14)
C15A—N1A—C10A—C9A	173.36 (9)	C15B—N1B—C10B—C9B	−169.87 (8)
C13A—N1A—C10A—C11A	−175.54 (9)	C13B—N1B—C10B—C11B	−173.64 (9)
C15A—N1A—C10A—C11A	−8.34 (14)	C15B—N1B—C10B—C11B	11.27 (13)
C8A—C9A—C10A—N1A	175.15 (9)	C8B—C9B—C10B—N1B	−178.65 (8)
C8A—C9A—C10A—C11A	−3.23 (13)	C8B—C9B—C10B—C11B	0.26 (13)
N1A—C10A—C11A—C12A	−174.48 (9)	N1B—C10B—C11B—C12B	178.45 (9)
C9A—C10A—C11A—C12A	3.90 (14)	C9B—C10B—C11B—C12B	−0.47 (13)
C10A—C11A—C12A—C7A	−1.67 (15)	C10B—C11B—C12B—C7B	0.54 (14)
C8A—C7A—C12A—C11A	−1.30 (14)	C8B—C7B—C12B—C11B	−0.37 (13)
C6A—C7A—C12A—C11A	179.13 (9)	C6B—C7B—C12B—C11B	−177.80 (9)
C10A—N1A—C13A—C14A	76.12 (11)	C10B—N1B—C13B—C14B	−89.58 (11)
C15A—N1A—C13A—C14A	−91.65 (11)	C15B—N1B—C13B—C14B	85.66 (11)
C10A—N1A—C15A—C16A	−77.83 (12)	C10B—N1B—C15B—C16B	73.16 (11)
C13A—N1A—C15A—C16A	89.76 (11)	C13B—N1B—C15B—C16B	−102.11 (10)
C1A—C5A—C17A—C18A	174.01 (9)	C1B—C5B—C17B—C18B	174.56 (9)
C4A—C5A—C17A—C18A	1.31 (18)	C4B—C5B—C17B—C18B	−3.88 (17)
C5A—C17A—C18A—C19A	21.55 (17)	C5B—C17B—C18B—C23B	−178.39 (9)
C5A—C17A—C18A—C23A	−157.33 (10)	C5B—C17B—C18B—C19B	0.35 (16)
C23A—C18A—C19A—C20A	1.36 (14)	C23B—C18B—C19B—C20B	0.10 (14)
C17A—C18A—C19A—C20A	−177.53 (9)	C17B—C18B—C19B—C20B	−178.66 (9)
C18A—C19A—C20A—C21A	0.67 (14)	C18B—C19B—C20B—C21B	1.01 (16)
C24A—N2A—C21A—C22A	4.98 (14)	C26B—N2B—C21B—C22B	−177.66 (9)
C26A—N2A—C21A—C22A	−176.97 (9)	C24B—N2B—C21B—C22B	−14.42 (14)
C24A—N2A—C21A—C20A	−175.03 (9)	C26B—N2B—C21B—C20B	2.95 (14)
C26A—N2A—C21A—C20A	3.02 (14)	C24B—N2B—C21B—C20B	166.19 (10)
C19A—C20A—C21A—N2A	178.06 (9)	C19B—C20B—C21B—N2B	178.36 (9)
C19A—C20A—C21A—C22A	−1.94 (13)	C19B—C20B—C21B—C22B	−1.05 (15)
N2A—C21A—C22A—C23A	−178.83 (9)	N2B—C21B—C22B—C23B	−179.39 (9)
C20A—C21A—C22A—C23A	1.18 (14)	C20B—C21B—C22B—C23B	0.02 (14)
C21A—C22A—C23A—C18A	0.88 (15)	C21B—C22B—C23B—C18B	1.11 (15)
C19A—C18A—C23A—C22A	−2.14 (14)	C19B—C18B—C23B—C22B	−1.15 (14)
C17A—C18A—C23A—C22A	176.84 (9)	C17B—C18B—C23B—C22B	177.70 (9)
C21A—N2A—C24A—C25A	−86.53 (11)	C21B—N2B—C24B—C25B	95.54 (12)
C26A—N2A—C24A—C25A	95.28 (10)	C26B—N2B—C24B—C25B	−100.27 (11)
C21A—N2A—C26A—C27A	−88.54 (11)	C21B—N2B—C26B—C27B	81.33 (12)
C24A—N2A—C26A—C27A	89.60 (10)	C24B—N2B—C26B—C27B	−82.68 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11B—H11B···O1A^i	0.95	2.45	3.3140 (12)	151
C15B—H15C···O1A^i	0.99	2.41	3.3714 (13)	164

Symmetry code: (i) x−1, y, z.

2,6-Bis[4-(diethylamino)benzylidene]cyclohexanone (III)

Crystal data

C28H36N2O	Z = 4
Mr = 416.59	F(000) = 904
Triclinic, P1	Dx = 1.167 Mg m^−3
a = 11.224 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.874 (10) Å	Cell parameters from 5462 reflections
c = 16.930 (12) Å	θ = 2.5–27.9°
α = 87.69 (2)°	µ = 0.07 mm^−1
β = 77.110 (16)°	T = 170 K
γ = 67.445 (14)°	Block, orange
V = 2370 (3) Å^3	0.30 × 0.26 × 0.22 mm

Data collection

Bruker APEXII CCD diffractometer	8431 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.053
φ and ω scans	θmax = 29.5°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −15→15
Tmin = 0.970, Tmax = 0.975	k = −18→19
26055 measured reflections	l = −23→23
13029 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.061	H-atom parameters constrained
wR(F^2) = 0.166	w = 1/[σ^2(Fo^2) + (0.0581P)^2 + 0.5151P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
13029 reflections	Δρmax = 0.57 e Å^−3
585 parameters	Δρmin = −0.45 e Å^−3
17 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: difference Fourier map	Extinction coefficient: 0.0045 (7)

Special details

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. The single crystal X-ray diffraction data were collected on a Bruker SMART APEX II diffractometer equipped with CCD area detector (λMoKa-radiation, graphite monochromator, φ- and ω-scan mode). The semi-empirical absorption correction was applied using the SADABS program (Bruker, 2016). The structures were determined by direct methods and refined by full-matrix least-square technique on F² in anisotropic approximation for non-hydrogen atoms.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1A	0.26453 (18)	0.59594 (10)	1.02746 (8)	0.0632 (4)
N1A	0.30243 (18)	0.36069 (12)	0.57638 (8)	0.0515 (4)
N2A	0.24044 (15)	1.08139 (11)	1.31290 (8)	0.0397 (3)
C1A	0.24155 (18)	0.67250 (13)	0.98545 (10)	0.0386 (4)
C2A	0.23499 (16)	0.66197 (12)	0.89926 (9)	0.0340 (3)
C3A	0.18362 (18)	0.75987 (12)	0.85413 (10)	0.0387 (4)
H3A	0.1321	0.7491	0.8173	0.046*
H3B	0.2596	0.7730	0.8204	0.046*
C4A	0.09665 (17)	0.85507 (13)	0.91055 (10)	0.0385 (4)
H4A	0.0155	0.8456	0.9400	0.046*
H4B	0.0697	0.9176	0.8781	0.046*
C5A	0.16850 (18)	0.87246 (13)	0.97154 (10)	0.0383 (4)
H5A	0.2427	0.8914	0.9424	0.046*
H5B	0.1067	0.9317	1.0097	0.046*
C6A	0.22176 (16)	0.77706 (12)	1.01887 (9)	0.0341 (3)
C7A	0.27610 (17)	0.56309 (13)	0.86901 (9)	0.0359 (4)
H7A	0.3071	0.5119	0.9065	0.043*
C8A	0.28291 (16)	0.51871 (12)	0.79126 (9)	0.0342 (3)
C9A	0.31381 (19)	0.41066 (13)	0.78593 (10)	0.0411 (4)
H9A	0.3318	0.3715	0.8322	0.049*
C10A	0.3192 (2)	0.35894 (14)	0.71691 (11)	0.0444 (4)
H10A	0.3406	0.2857	0.7168	0.053*
C11A	0.29366 (18)	0.41269 (13)	0.64635 (10)	0.0377 (4)
C12A	0.26437 (18)	0.52140 (13)	0.65098 (10)	0.0392 (4)
H12A	0.2468	0.5608	0.6047	0.047*
C13A	0.26062 (18)	0.57139 (13)	0.71997 (10)	0.0388 (4)
H13A	0.2423	0.6442	0.7198	0.047*
C14A	0.36497 (19)	0.24744 (14)	0.56827 (11)	0.0438 (4)
H14A	0.4368	0.2238	0.5982	0.053*
H14B	0.4059	0.2261	0.5103	0.053*
C15A	0.2713 (2)	0.19253 (15)	0.59934 (12)	0.0497 (5)
H15A	0.2287	0.2142	0.6564	0.075*
H15B	0.3212	0.1167	0.5944	0.075*
H15C	0.2036	0.2111	0.5673	0.075*
C16A	0.2676 (7)	0.4187 (4)	0.5047 (3)	0.0636 (8)	0.6
H16A	0.3498	0.4191	0.4683	0.076*	0.6
H16B	0.2099	0.4921	0.5227	0.076*	0.6
C17A	0.1994 (5)	0.3776 (3)	0.4572 (3)	0.0794 (13)	0.6
H17A	0.1774	0.4229	0.4123	0.119*	0.6
H17B	0.1180	0.3763	0.4925	0.119*	0.6
H17C	0.2579	0.3067	0.4356	0.119*	0.6
C16C	0.2830 (8)	0.4124 (7)	0.5000 (4)	0.0636 (8)	0.4
H16E	0.3486	0.3665	0.4539	0.076*	0.4
H16F	0.2980	0.4782	0.5004	0.076*	0.4
C17C	0.1450 (7)	0.4364 (5)	0.4886 (4)	0.0794 (13)	0.4
H17G	0.1351	0.4701	0.4371	0.119*	0.4
H17H	0.0800	0.4834	0.5334	0.119*	0.4
H17I	0.1302	0.3713	0.4878	0.119*	0.4
C18A	0.25441 (16)	0.77725 (13)	1.09108 (10)	0.0355 (4)
H18A	0.2855	0.7099	1.1123	0.043*
C19A	0.25164 (16)	0.85949 (13)	1.14276 (9)	0.0334 (3)
C20A	0.23007 (16)	0.96362 (13)	1.12365 (10)	0.0349 (3)
H20A	0.2181	0.9849	1.0710	0.042*
C21A	0.22577 (16)	1.03554 (13)	1.17894 (10)	0.0356 (4)
H21A	0.2090	1.1054	1.1636	0.043*
C22A	0.24542 (15)	1.00890 (13)	1.25757 (9)	0.0331 (3)
C23A	0.27165 (17)	0.90390 (13)	1.27630 (10)	0.0376 (4)
H23A	0.2877	0.8817	1.3281	0.045*
C24A	0.27429 (17)	0.83305 (13)	1.22065 (10)	0.0378 (4)
H24A	0.2923	0.7630	1.2356	0.045*
C25A	0.25111 (18)	1.05551 (15)	1.39611 (10)	0.0416 (4)
H25A	0.2127	1.0025	1.4132	0.050*
H25B	0.1987	1.1189	1.4323	0.050*
C26A	0.3927 (2)	1.01369 (18)	1.40607 (13)	0.0598 (6)
H26A	0.3951	0.9914	1.4616	0.090*
H26B	0.4280	1.0687	1.3955	0.090*
H26C	0.4467	0.9540	1.3676	0.090*
C27A	0.2277 (2)	1.18698 (14)	1.29172 (11)	0.0462 (4)
H27A	0.2714	1.1857	1.2339	0.055*
H27B	0.2747	1.2113	1.3244	0.055*
C28A	0.0859 (2)	1.26386 (16)	1.30547 (14)	0.0628 (6)
H28A	0.0433	1.2685	1.3632	0.094*
H28B	0.0384	1.2402	1.2735	0.094*
H28C	0.0838	1.3328	1.2886	0.094*
O1B	0.42123 (14)	0.79296 (11)	0.65049 (9)	0.0658 (4)
N1B	0.26820 (15)	1.28364 (12)	0.97327 (9)	0.0488 (4)
N2B	0.23083 (14)	0.56611 (14)	0.27143 (10)	0.0600 (5)
C1B	0.30762 (17)	0.85431 (13)	0.65005 (10)	0.0375 (4)
C2B	0.24167 (16)	0.94897 (12)	0.70648 (9)	0.0327 (3)
C3B	0.10331 (16)	1.02284 (13)	0.70292 (10)	0.0362 (4)
H3C	0.0900	1.0944	0.7200	0.043*
H3D	0.0383	1.0017	0.7414	0.043*
C4B	0.07872 (17)	1.02354 (13)	0.61810 (10)	0.0365 (4)
H4C	−0.0131	1.0720	0.6184	0.044*
H4D	0.1398	1.0491	0.5802	0.044*
C5B	0.09949 (16)	0.91504 (12)	0.58903 (10)	0.0360 (4)
H5C	0.0316	0.8930	0.6235	0.043*
H5D	0.0876	0.9173	0.5327	0.043*
C6B	0.23526 (16)	0.83553 (12)	0.59171 (9)	0.0330 (3)
C7B	0.31577 (17)	0.96332 (13)	0.75419 (10)	0.0357 (4)
H7B	0.4006	0.9084	0.7478	0.043*
C8B	0.29266 (16)	1.04528 (13)	0.81319 (9)	0.0345 (3)
C9B	0.40440 (17)	1.05361 (14)	0.83090 (10)	0.0416 (4)
H9B	0.4892	1.0042	0.8054	0.050*
C10B	0.39773 (17)	1.12977 (15)	0.88336 (11)	0.0437 (4)
H10B	0.4771	1.1321	0.8925	0.052*
C11B	0.27463 (17)	1.20424 (14)	0.92360 (10)	0.0384 (4)
C12B	0.16133 (17)	1.19364 (14)	0.90918 (10)	0.0409 (4)
H12B	0.0764	1.2404	0.9371	0.049*
C13B	0.16963 (17)	1.11773 (14)	0.85588 (10)	0.0384 (4)
H13B	0.0904	1.1141	0.8476	0.046*
C14B	0.38784 (19)	1.28425 (16)	0.99371 (11)	0.0482 (5)
H14C	0.3677	1.3542	1.0177	0.058*
H14D	0.4567	1.2730	0.9431	0.058*
C15B	0.4433 (2)	1.20289 (19)	1.05204 (12)	0.0609 (6)
H15D	0.4626	1.1333	1.0293	0.091*
H15E	0.3783	1.2161	1.1039	0.091*
H15F	0.5249	1.2065	1.0608	0.091*
C16B	0.1427 (2)	1.37122 (16)	1.00799 (12)	0.0510 (5)	0.9
H16C	0.0769	1.3774	0.9757	0.061*	0.9
H16D	0.1579	1.4372	1.0046	0.061*	0.9
C17B	0.0884 (3)	1.3559 (2)	1.09493 (13)	0.0711 (7)	0.9
H17D	0.0054	1.4153	1.1159	0.107*	0.9
H17E	0.1527	1.3511	1.1273	0.107*	0.9
H17F	0.0717	1.2913	1.0983	0.107*	0.9
C16D	0.1581 (14)	1.3071 (13)	1.0461 (8)	0.0510 (5)	0.1
H16G	0.1928	1.2902	1.0959	0.061*	0.1
H16H	0.1037	1.2662	1.0430	0.061*	0.1
C17D	0.077 (2)	1.4230 (14)	1.0460 (15)	0.0711 (7)	0.1
H17J	0.0020	1.4435	1.0932	0.107*	0.1
H17K	0.0436	1.4384	0.9962	0.107*	0.1
H17L	0.1324	1.4622	1.0486	0.107*	0.1
C18B	0.30196 (17)	0.74889 (13)	0.54236 (10)	0.0353 (3)
H18B	0.3861	0.7077	0.5529	0.042*
C19B	0.27156 (16)	0.70540 (12)	0.47617 (9)	0.0338 (3)
C20B	0.14738 (16)	0.72720 (13)	0.45958 (10)	0.0359 (4)
H20B	0.0707	0.7750	0.4949	0.043*
C21B	0.13293 (17)	0.68116 (14)	0.39332 (10)	0.0404 (4)
H21B	0.0467	0.6974	0.3847	0.048*
C22B	0.24336 (17)	0.61056 (13)	0.33824 (10)	0.0379 (4)
C23B	0.36779 (16)	0.58682 (13)	0.35566 (10)	0.0377 (4)
H23B	0.4448	0.5389	0.3206	0.045*
C24B	0.37978 (17)	0.63171 (14)	0.42246 (10)	0.0395 (4)
H24B	0.4654	0.6121	0.4331	0.047*
C25B	0.34634 (19)	0.50222 (15)	0.20991 (11)	0.0467 (4)
H25C	0.4163	0.5304	0.2047	0.056*
H25D	0.3212	0.5076	0.1570	0.056*
C26B	0.4014 (2)	0.38889 (17)	0.22926 (15)	0.0634 (6)
H26D	0.4756	0.3496	0.1849	0.095*
H26E	0.3321	0.3608	0.2358	0.095*
H26F	0.4324	0.3825	0.2797	0.095*
C27B	0.0990 (2)	0.56322 (18)	0.26725 (15)	0.0457 (5)	0.75
H27C	0.0424	0.5714	0.3225	0.055*	0.75
H27D	0.1126	0.4954	0.2423	0.055*	0.75
C28B	0.0328 (3)	0.6518 (2)	0.21651 (17)	0.0615 (7)	0.75
H28D	−0.0538	0.6523	0.2141	0.092*	0.75
H28E	0.0883	0.6420	0.1615	0.092*	0.75
H28F	0.0212	0.7185	0.2411	0.092*	0.75
C27C	0.1149 (5)	0.6220 (5)	0.2349 (4)	0.0457 (5)	0.25
H27E	0.1442	0.6180	0.1750	0.055*	0.25
H27F	0.0744	0.6966	0.2537	0.055*	0.25
C28C	0.0136 (5)	0.5719 (7)	0.2599 (5)	0.0615 (7)	0.25
H28G	−0.0631	0.6089	0.2364	0.092*	0.25
H28H	−0.0150	0.5761	0.3192	0.092*	0.25
H28I	0.0538	0.4984	0.2403	0.092*	0.25

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.1207 (13)	0.0393 (7)	0.0358 (7)	−0.0335 (8)	−0.0261 (8)	0.0093 (6)
N1A	0.0916 (13)	0.0419 (9)	0.0397 (8)	−0.0389 (9)	−0.0289 (8)	0.0087 (7)
N2A	0.0502 (9)	0.0400 (8)	0.0336 (7)	−0.0203 (7)	−0.0137 (6)	0.0023 (6)
C1A	0.0511 (10)	0.0352 (9)	0.0306 (8)	−0.0173 (8)	−0.0103 (7)	0.0046 (7)
C2A	0.0393 (9)	0.0337 (8)	0.0288 (7)	−0.0147 (7)	−0.0063 (6)	0.0022 (6)
C3A	0.0476 (10)	0.0335 (8)	0.0312 (8)	−0.0104 (7)	−0.0107 (7)	0.0022 (6)
C4A	0.0415 (9)	0.0351 (9)	0.0361 (8)	−0.0098 (7)	−0.0123 (7)	0.0012 (7)
C5A	0.0443 (10)	0.0318 (8)	0.0384 (9)	−0.0111 (7)	−0.0148 (7)	0.0010 (7)
C6A	0.0364 (8)	0.0328 (8)	0.0320 (8)	−0.0133 (7)	−0.0055 (6)	0.0016 (6)
C7A	0.0428 (9)	0.0338 (8)	0.0307 (8)	−0.0151 (7)	−0.0076 (7)	0.0056 (6)
C8A	0.0386 (9)	0.0323 (8)	0.0316 (8)	−0.0139 (7)	−0.0071 (7)	0.0022 (6)
C9A	0.0593 (11)	0.0343 (9)	0.0347 (8)	−0.0203 (8)	−0.0178 (8)	0.0097 (7)
C10A	0.0678 (12)	0.0328 (9)	0.0416 (9)	−0.0255 (9)	−0.0203 (9)	0.0084 (7)
C11A	0.0480 (10)	0.0382 (9)	0.0354 (8)	−0.0234 (8)	−0.0140 (7)	0.0053 (7)
C12A	0.0494 (10)	0.0341 (9)	0.0322 (8)	−0.0142 (8)	−0.0099 (7)	0.0070 (7)
C13A	0.0489 (10)	0.0282 (8)	0.0347 (8)	−0.0118 (7)	−0.0065 (7)	0.0042 (6)
C14A	0.0535 (11)	0.0447 (10)	0.0407 (9)	−0.0269 (9)	−0.0102 (8)	−0.0016 (8)
C15A	0.0551 (12)	0.0408 (10)	0.0597 (12)	−0.0259 (9)	−0.0115 (9)	0.0000 (9)
C16A	0.112 (2)	0.0635 (15)	0.0445 (12)	−0.0564 (16)	−0.0377 (14)	0.0195 (10)
C17A	0.122 (4)	0.061 (3)	0.082 (3)	−0.045 (3)	−0.061 (3)	0.027 (2)
C16C	0.112 (2)	0.0635 (15)	0.0445 (12)	−0.0564 (16)	−0.0377 (14)	0.0195 (10)
C17C	0.122 (4)	0.061 (3)	0.082 (3)	−0.045 (3)	−0.061 (3)	0.027 (2)
C18A	0.0389 (9)	0.0336 (8)	0.0338 (8)	−0.0143 (7)	−0.0078 (7)	0.0044 (6)
C19A	0.0325 (8)	0.0356 (8)	0.0335 (8)	−0.0142 (7)	−0.0082 (6)	0.0036 (6)
C20A	0.0391 (9)	0.0370 (9)	0.0312 (8)	−0.0161 (7)	−0.0112 (7)	0.0071 (6)
C21A	0.0394 (9)	0.0335 (8)	0.0367 (8)	−0.0157 (7)	−0.0122 (7)	0.0069 (7)
C22A	0.0301 (8)	0.0381 (8)	0.0331 (8)	−0.0149 (7)	−0.0075 (6)	0.0013 (6)
C23A	0.0434 (9)	0.0407 (9)	0.0318 (8)	−0.0179 (8)	−0.0124 (7)	0.0074 (7)
C24A	0.0448 (9)	0.0347 (9)	0.0372 (8)	−0.0175 (7)	−0.0128 (7)	0.0076 (7)
C25A	0.0460 (10)	0.0468 (10)	0.0322 (8)	−0.0176 (8)	−0.0091 (7)	−0.0014 (7)
C26A	0.0543 (12)	0.0718 (14)	0.0509 (11)	−0.0149 (11)	−0.0233 (10)	−0.0025 (10)
C27A	0.0636 (12)	0.0458 (10)	0.0394 (9)	−0.0333 (10)	−0.0092 (8)	0.0010 (8)
C28A	0.0810 (16)	0.0404 (11)	0.0595 (13)	−0.0188 (11)	−0.0102 (11)	0.0091 (9)
O1B	0.0552 (9)	0.0543 (9)	0.0766 (10)	0.0065 (7)	−0.0376 (8)	−0.0242 (7)
N1B	0.0434 (9)	0.0561 (10)	0.0442 (8)	−0.0162 (8)	−0.0067 (7)	−0.0168 (7)
N2B	0.0403 (9)	0.0738 (12)	0.0561 (10)	−0.0036 (8)	−0.0193 (8)	−0.0293 (9)
C1B	0.0408 (9)	0.0348 (9)	0.0373 (9)	−0.0122 (7)	−0.0133 (7)	0.0000 (7)
C2B	0.0370 (8)	0.0324 (8)	0.0298 (7)	−0.0153 (7)	−0.0063 (6)	0.0033 (6)
C3B	0.0370 (9)	0.0374 (9)	0.0344 (8)	−0.0143 (7)	−0.0080 (7)	0.0001 (7)
C4B	0.0393 (9)	0.0339 (8)	0.0384 (8)	−0.0143 (7)	−0.0131 (7)	0.0046 (7)
C5B	0.0382 (9)	0.0336 (8)	0.0399 (9)	−0.0157 (7)	−0.0125 (7)	0.0026 (7)
C6B	0.0374 (9)	0.0333 (8)	0.0320 (8)	−0.0173 (7)	−0.0090 (6)	0.0043 (6)
C7B	0.0357 (9)	0.0369 (9)	0.0346 (8)	−0.0139 (7)	−0.0081 (7)	0.0015 (7)
C8B	0.0360 (8)	0.0408 (9)	0.0300 (7)	−0.0183 (7)	−0.0078 (6)	0.0024 (6)
C9B	0.0336 (9)	0.0484 (10)	0.0404 (9)	−0.0134 (8)	−0.0065 (7)	−0.0073 (8)
C10B	0.0345 (9)	0.0553 (11)	0.0427 (9)	−0.0178 (8)	−0.0085 (7)	−0.0089 (8)
C11B	0.0402 (9)	0.0460 (10)	0.0299 (8)	−0.0191 (8)	−0.0047 (7)	−0.0026 (7)
C12B	0.0330 (9)	0.0504 (10)	0.0351 (8)	−0.0142 (8)	−0.0013 (7)	−0.0053 (7)
C13B	0.0333 (8)	0.0511 (10)	0.0334 (8)	−0.0199 (8)	−0.0053 (7)	−0.0005 (7)
C14B	0.0498 (11)	0.0594 (12)	0.0412 (10)	−0.0288 (10)	−0.0056 (8)	−0.0094 (9)
C15B	0.0603 (13)	0.0842 (16)	0.0442 (11)	−0.0326 (12)	−0.0140 (10)	−0.0001 (11)
C16B	0.0553 (13)	0.0479 (12)	0.0483 (12)	−0.0179 (11)	−0.0105 (10)	−0.0078 (10)
C17B	0.0541 (15)	0.099 (2)	0.0521 (14)	−0.0255 (15)	−0.0010 (12)	−0.0080 (14)
C16D	0.0553 (13)	0.0479 (12)	0.0483 (12)	−0.0179 (11)	−0.0105 (10)	−0.0078 (10)
C17D	0.0541 (15)	0.099 (2)	0.0521 (14)	−0.0255 (15)	−0.0010 (12)	−0.0080 (14)
C18B	0.0368 (9)	0.0356 (8)	0.0355 (8)	−0.0149 (7)	−0.0106 (7)	0.0021 (7)
C19B	0.0373 (9)	0.0326 (8)	0.0335 (8)	−0.0160 (7)	−0.0074 (7)	0.0025 (6)
C20B	0.0335 (8)	0.0352 (8)	0.0374 (8)	−0.0132 (7)	−0.0040 (7)	−0.0020 (7)
C21B	0.0337 (9)	0.0437 (10)	0.0442 (9)	−0.0129 (7)	−0.0121 (7)	−0.0037 (8)
C22B	0.0394 (9)	0.0372 (9)	0.0378 (9)	−0.0133 (7)	−0.0118 (7)	−0.0028 (7)
C23B	0.0336 (8)	0.0402 (9)	0.0372 (9)	−0.0130 (7)	−0.0050 (7)	−0.0044 (7)
C24B	0.0319 (8)	0.0425 (9)	0.0435 (9)	−0.0132 (7)	−0.0085 (7)	−0.0048 (7)
C25B	0.0501 (11)	0.0491 (11)	0.0373 (9)	−0.0131 (9)	−0.0122 (8)	−0.0058 (8)
C26B	0.0689 (15)	0.0495 (12)	0.0705 (14)	−0.0204 (11)	−0.0165 (12)	−0.0035 (10)
C27B	0.0571 (15)	0.0412 (13)	0.0423 (13)	−0.0192 (12)	−0.0174 (11)	0.0010 (9)
C28B	0.0572 (16)	0.0696 (19)	0.0577 (16)	−0.0222 (15)	−0.0180 (13)	0.0109 (13)
C27C	0.0571 (15)	0.0412 (13)	0.0423 (13)	−0.0192 (12)	−0.0174 (11)	0.0010 (9)
C28C	0.0572 (16)	0.0696 (19)	0.0577 (16)	−0.0222 (15)	−0.0180 (13)	0.0109 (13)

Geometric parameters (Å, º)

O1A—C1A	1.229 (2)	N1B—C16D	1.482 (3)
N1A—C11A	1.377 (2)	N2B—C22B	1.369 (2)
N1A—C14A	1.452 (3)	N2B—C25B	1.464 (2)
N1A—C16A	1.471 (3)	N2B—C27C	1.491 (3)
N1A—C16C	1.471 (3)	N2B—C27B	1.513 (2)
N2A—C22A	1.379 (2)	C1B—C2B	1.492 (2)
N2A—C27A	1.454 (2)	C1B—C6B	1.498 (2)
N2A—C25A	1.459 (2)	C2B—C7B	1.350 (2)
C1A—C2A	1.493 (2)	C2B—C3B	1.511 (2)
C1A—C6A	1.496 (2)	C3B—C4B	1.521 (2)
C2A—C7A	1.350 (2)	C3B—H3C	0.9900
C2A—C3A	1.508 (2)	C3B—H3D	0.9900
C3A—C4A	1.519 (2)	C4B—C5B	1.517 (2)
C3A—H3A	0.9900	C4B—H4C	0.9900
C3A—H3B	0.9900	C4B—H4D	0.9900
C4A—C5A	1.522 (2)	C5B—C6B	1.510 (2)
C4A—H4A	0.9900	C5B—H5C	0.9900
C4A—H4B	0.9900	C5B—H5D	0.9900
C5A—C6A	1.507 (2)	C6B—C18B	1.347 (2)
C5A—H5A	0.9900	C7B—C8B	1.452 (2)
C5A—H5B	0.9900	C7B—H7B	0.9500
C6A—C18A	1.353 (2)	C8B—C9B	1.399 (2)
C7A—C8A	1.450 (2)	C8B—C13B	1.410 (2)
C7A—H7A	0.9500	C9B—C10B	1.377 (2)
C8A—C9A	1.405 (3)	C9B—H9B	0.9500
C8A—C13A	1.406 (2)	C10B—C11B	1.408 (3)
C9A—C10A	1.374 (2)	C10B—H10B	0.9500
C9A—H9A	0.9500	C11B—C12B	1.408 (3)
C10A—C11A	1.408 (2)	C12B—C13B	1.377 (2)
C10A—H10A	0.9500	C12B—H12B	0.9500
C11A—C12A	1.417 (3)	C13B—H13B	0.9500
C12A—C13A	1.367 (2)	C14B—C15B	1.511 (3)
C12A—H12A	0.9500	C14B—H14C	0.9900
C13A—H13A	0.9500	C14B—H14D	0.9900
C14A—C15A	1.516 (3)	C15B—H15D	0.9800
C14A—H14A	0.9900	C15B—H15E	0.9800
C14A—H14B	0.9900	C15B—H15F	0.9800
C15A—H15A	0.9800	C16B—C17B	1.502 (2)
C15A—H15B	0.9800	C16B—H16C	0.9900
C15A—H15C	0.9800	C16B—H16D	0.9900
C16A—C17A	1.484 (3)	C17B—H17D	0.9800
C16A—H16A	0.9900	C17B—H17E	0.9800
C16A—H16B	0.9900	C17B—H17F	0.9800
C17A—H17A	0.9800	C16D—C17D	1.514 (3)
C17A—H17B	0.9800	C16D—H16G	0.9900
C17A—H17C	0.9800	C16D—H16H	0.9900
C16C—C17C	1.511 (3)	C17D—H17J	0.9800
C16C—H16E	0.9900	C17D—H17K	0.9800
C16C—H16F	0.9900	C17D—H17L	0.9800
C17C—H17G	0.9800	C18B—C19B	1.456 (2)
C17C—H17H	0.9800	C18B—H18B	0.9500
C17C—H17I	0.9800	C19B—C20B	1.399 (2)
C18A—C19A	1.452 (2)	C19B—C24B	1.406 (2)
C18A—H18A	0.9500	C20B—C21B	1.382 (2)
C19A—C24A	1.406 (2)	C20B—H20B	0.9500
C19A—C20A	1.407 (2)	C21B—C22B	1.411 (2)
C20A—C21A	1.376 (2)	C21B—H21B	0.9500
C20A—H20A	0.9500	C22B—C23B	1.403 (3)
C21A—C22A	1.409 (2)	C23B—C24B	1.369 (2)
C21A—H21A	0.9500	C23B—H23B	0.9500
C22A—C23A	1.409 (3)	C24B—H24B	0.9500
C23A—C24A	1.376 (2)	C25B—C26B	1.505 (3)
C23A—H23A	0.9500	C25B—H25C	0.9900
C24A—H24A	0.9500	C25B—H25D	0.9900
C25A—C26A	1.515 (3)	C26B—H26D	0.9800
C25A—H25A	0.9900	C26B—H26E	0.9800
C25A—H25B	0.9900	C26B—H26F	0.9800
C26A—H26A	0.9800	C27B—C28B	1.517 (2)
C26A—H26B	0.9800	C27B—H27C	0.9900
C26A—H26C	0.9800	C27B—H27D	0.9900
C27A—C28A	1.510 (3)	C28B—H28D	0.9800
C27A—H27A	0.9900	C28B—H28E	0.9800
C27A—H27B	0.9900	C28B—H28F	0.9800
C28A—H28A	0.9800	C27C—C28C	1.525 (3)
C28A—H28B	0.9800	C27C—H27E	0.9900
C28A—H28C	0.9800	C27C—H27F	0.9900
O1B—C1B	1.234 (2)	C28C—H28G	0.9800
N1B—C11B	1.383 (2)	C28C—H28H	0.9800
N1B—C14B	1.463 (3)	C28C—H28I	0.9800
N1B—C16B	1.477 (2)
C11A—N1A—C14A	120.08 (14)	C25B—N2B—C27C	111.2 (3)
C11A—N1A—C16A	120.6 (3)	C22B—N2B—C27B	120.29 (16)
C14A—N1A—C16A	118.7 (3)	C25B—N2B—C27B	116.80 (16)
C11A—N1A—C16C	123.3 (4)	O1B—C1B—C2B	120.44 (15)
C14A—N1A—C16C	114.8 (4)	O1B—C1B—C6B	120.29 (16)
C22A—N2A—C27A	122.39 (15)	C2B—C1B—C6B	119.26 (15)
C22A—N2A—C25A	121.68 (15)	C7B—C2B—C1B	115.72 (15)
C27A—N2A—C25A	115.91 (14)	C7B—C2B—C3B	125.55 (15)
O1A—C1A—C2A	120.21 (15)	C1B—C2B—C3B	118.64 (14)
O1A—C1A—C6A	121.00 (15)	C2B—C3B—C4B	111.79 (14)
C2A—C1A—C6A	118.79 (14)	C2B—C3B—H3C	109.3
C7A—C2A—C1A	115.52 (14)	C4B—C3B—H3C	109.3
C7A—C2A—C3A	125.88 (15)	C2B—C3B—H3D	109.3
C1A—C2A—C3A	118.60 (14)	C4B—C3B—H3D	109.3
C2A—C3A—C4A	112.65 (14)	H3C—C3B—H3D	107.9
C2A—C3A—H3A	109.1	C5B—C4B—C3B	111.10 (14)
C4A—C3A—H3A	109.1	C5B—C4B—H4C	109.4
C2A—C3A—H3B	109.1	C3B—C4B—H4C	109.4
C4A—C3A—H3B	109.1	C5B—C4B—H4D	109.4
H3A—C3A—H3B	107.8	C3B—C4B—H4D	109.4
C3A—C4A—C5A	111.50 (15)	H4C—C4B—H4D	108.0
C3A—C4A—H4A	109.3	C6B—C5B—C4B	112.30 (14)
C5A—C4A—H4A	109.3	C6B—C5B—H5C	109.1
C3A—C4A—H4B	109.3	C4B—C5B—H5C	109.1
C5A—C4A—H4B	109.3	C6B—C5B—H5D	109.1
H4A—C4A—H4B	108.0	C4B—C5B—H5D	109.1
C6A—C5A—C4A	112.30 (14)	H5C—C5B—H5D	107.9
C6A—C5A—H5A	109.1	C18B—C6B—C1B	115.64 (15)
C4A—C5A—H5A	109.1	C18B—C6B—C5B	125.06 (15)
C6A—C5A—H5B	109.1	C1B—C6B—C5B	119.23 (14)
C4A—C5A—H5B	109.1	C2B—C7B—C8B	133.28 (16)
H5A—C5A—H5B	107.9	C2B—C7B—H7B	113.4
C18A—C6A—C1A	115.63 (14)	C8B—C7B—H7B	113.4
C18A—C6A—C5A	125.12 (15)	C9B—C8B—C13B	115.57 (16)
C1A—C6A—C5A	119.25 (15)	C9B—C8B—C7B	116.98 (15)
C2A—C7A—C8A	133.45 (15)	C13B—C8B—C7B	127.45 (15)
C2A—C7A—H7A	113.3	C10B—C9B—C8B	123.37 (16)
C8A—C7A—H7A	113.3	C10B—C9B—H9B	118.3
C9A—C8A—C13A	115.51 (15)	C8B—C9B—H9B	118.3
C9A—C8A—C7A	116.88 (14)	C9B—C10B—C11B	120.75 (17)
C13A—C8A—C7A	127.61 (15)	C9B—C10B—H10B	119.6
C10A—C9A—C8A	123.09 (15)	C11B—C10B—H10B	119.6
C10A—C9A—H9A	118.5	N1B—C11B—C10B	120.68 (16)
C8A—C9A—H9A	118.5	N1B—C11B—C12B	122.95 (16)
C9A—C10A—C11A	121.06 (16)	C10B—C11B—C12B	116.36 (16)
C9A—C10A—H10A	119.5	C13B—C12B—C11B	122.15 (16)
C11A—C10A—H10A	119.5	C13B—C12B—H12B	118.9
N1A—C11A—C10A	121.23 (16)	C11B—C12B—H12B	118.9
N1A—C11A—C12A	122.61 (15)	C12B—C13B—C8B	121.69 (16)
C10A—C11A—C12A	116.10 (15)	C12B—C13B—H13B	119.2
C13A—C12A—C11A	122.02 (15)	C8B—C13B—H13B	119.2
C13A—C12A—H12A	119.0	N1B—C14B—C15B	114.52 (17)
C11A—C12A—H12A	119.0	N1B—C14B—H14C	108.6
C12A—C13A—C8A	122.19 (16)	C15B—C14B—H14C	108.6
C12A—C13A—H13A	118.9	N1B—C14B—H14D	108.6
C8A—C13A—H13A	118.9	C15B—C14B—H14D	108.6
N1A—C14A—C15A	114.16 (17)	H14C—C14B—H14D	107.6
N1A—C14A—H14A	108.7	C14B—C15B—H15D	109.5
C15A—C14A—H14A	108.7	C14B—C15B—H15E	109.5
N1A—C14A—H14B	108.7	H15D—C15B—H15E	109.5
C15A—C14A—H14B	108.7	C14B—C15B—H15F	109.5
H14A—C14A—H14B	107.6	H15D—C15B—H15F	109.5
C14A—C15A—H15A	109.5	H15E—C15B—H15F	109.5
C14A—C15A—H15B	109.5	N1B—C16B—C17B	111.71 (19)
H15A—C15A—H15B	109.5	N1B—C16B—H16C	109.3
C14A—C15A—H15C	109.5	C17B—C16B—H16C	109.3
H15A—C15A—H15C	109.5	N1B—C16B—H16D	109.3
H15B—C15A—H15C	109.5	C17B—C16B—H16D	109.3
N1A—C16A—C17A	115.6 (3)	H16C—C16B—H16D	107.9
N1A—C16A—H16A	108.4	C16B—C17B—H17D	109.5
C17A—C16A—H16A	108.4	C16B—C17B—H17E	109.5
N1A—C16A—H16B	108.4	H17D—C17B—H17E	109.5
C17A—C16A—H16B	108.4	C16B—C17B—H17F	109.5
H16A—C16A—H16B	107.4	H17D—C17B—H17F	109.5
C16A—C17A—H17A	109.5	H17E—C17B—H17F	109.5
C16A—C17A—H17B	109.5	N1B—C16D—C17D	105.6 (12)
H17A—C17A—H17B	109.5	N1B—C16D—H16G	110.6
C16A—C17A—H17C	109.5	C17D—C16D—H16G	110.6
H17A—C17A—H17C	109.5	N1B—C16D—H16H	110.6
H17B—C17A—H17C	109.5	C17D—C16D—H16H	110.6
N1A—C16C—C17C	111.2 (3)	H16G—C16D—H16H	108.8
N1A—C16C—H16E	109.4	C16D—C17D—H17J	109.5
C17C—C16C—H16E	109.4	C16D—C17D—H17K	109.5
N1A—C16C—H16F	109.4	H17J—C17D—H17K	109.5
C17C—C16C—H16F	109.4	C16D—C17D—H17L	109.5
H16E—C16C—H16F	108.0	H17J—C17D—H17L	109.5
C16C—C17C—H17G	109.5	H17K—C17D—H17L	109.5
C16C—C17C—H17H	109.5	C6B—C18B—C19B	133.15 (16)
H17G—C17C—H17H	109.5	C6B—C18B—H18B	113.4
C16C—C17C—H17I	109.5	C19B—C18B—H18B	113.4
H17G—C17C—H17I	109.5	C20B—C19B—C24B	115.67 (15)
H17H—C17C—H17I	109.5	C20B—C19B—C18B	128.00 (15)
C6A—C18A—C19A	133.04 (16)	C24B—C19B—C18B	116.33 (15)
C6A—C18A—H18A	113.5	C21B—C20B—C19B	121.94 (15)
C19A—C18A—H18A	113.5	C21B—C20B—H20B	119.0
C24A—C19A—C20A	115.48 (15)	C19B—C20B—H20B	119.0
C24A—C19A—C18A	117.13 (15)	C20B—C21B—C22B	121.51 (16)
C20A—C19A—C18A	127.39 (15)	C20B—C21B—H21B	119.2
C21A—C20A—C19A	122.00 (15)	C22B—C21B—H21B	119.2
C21A—C20A—H20A	119.0	N2B—C22B—C23B	121.15 (15)
C19A—C20A—H20A	119.0	N2B—C22B—C21B	122.17 (16)
C20A—C21A—C22A	122.06 (15)	C23B—C22B—C21B	116.68 (15)
C20A—C21A—H21A	119.0	C24B—C23B—C22B	120.90 (16)
C22A—C21A—H21A	119.0	C24B—C23B—H23B	119.6
N2A—C22A—C21A	121.85 (15)	C22B—C23B—H23B	119.6
N2A—C22A—C23A	121.82 (15)	C23B—C24B—C19B	123.22 (16)
C21A—C22A—C23A	116.33 (15)	C23B—C24B—H24B	118.4
C24A—C23A—C22A	120.94 (15)	C19B—C24B—H24B	118.4
C24A—C23A—H23A	119.5	N2B—C25B—C26B	113.19 (18)
C22A—C23A—H23A	119.5	N2B—C25B—H25C	108.9
C23A—C24A—C19A	123.12 (16)	C26B—C25B—H25C	108.9
C23A—C24A—H24A	118.4	N2B—C25B—H25D	108.9
C19A—C24A—H24A	118.4	C26B—C25B—H25D	108.9
N2A—C25A—C26A	112.87 (15)	H25C—C25B—H25D	107.8
N2A—C25A—H25A	109.0	C25B—C26B—H26D	109.5
C26A—C25A—H25A	109.0	C25B—C26B—H26E	109.5
N2A—C25A—H25B	109.0	H26D—C26B—H26E	109.5
C26A—C25A—H25B	109.0	C25B—C26B—H26F	109.5
H25A—C25A—H25B	107.8	H26D—C26B—H26F	109.5
C25A—C26A—H26A	109.5	H26E—C26B—H26F	109.5
C25A—C26A—H26B	109.5	N2B—C27B—C28B	108.22 (17)
H26A—C26A—H26B	109.5	N2B—C27B—H27C	110.1
C25A—C26A—H26C	109.5	C28B—C27B—H27C	110.1
H26A—C26A—H26C	109.5	N2B—C27B—H27D	110.1
H26B—C26A—H26C	109.5	C28B—C27B—H27D	110.1
N2A—C27A—C28A	113.37 (16)	H27C—C27B—H27D	108.4
N2A—C27A—H27A	108.9	C27B—C28B—H28D	109.5
C28A—C27A—H27A	108.9	C27B—C28B—H28E	109.5
N2A—C27A—H27B	108.9	H28D—C28B—H28E	109.5
C28A—C27A—H27B	108.9	C27B—C28B—H28F	109.5
H27A—C27A—H27B	107.7	H28D—C28B—H28F	109.5
C27A—C28A—H28A	109.5	H28E—C28B—H28F	109.5
C27A—C28A—H28B	109.5	N2B—C27C—C28C	109.3 (3)
H28A—C28A—H28B	109.5	N2B—C27C—H27E	109.8
C27A—C28A—H28C	109.5	C28C—C27C—H27E	109.8
H28A—C28A—H28C	109.5	N2B—C27C—H27F	109.8
H28B—C28A—H28C	109.5	C28C—C27C—H27F	109.8
C11B—N1B—C14B	120.70 (15)	H27E—C27C—H27F	108.3
C11B—N1B—C16B	122.57 (16)	C27C—C28C—H28G	109.5
C14B—N1B—C16B	116.73 (16)	C27C—C28C—H28H	109.5
C11B—N1B—C16D	112.0 (8)	H28G—C28C—H28H	109.5
C14B—N1B—C16D	111.3 (8)	C27C—C28C—H28I	109.5
C22B—N2B—C25B	121.80 (15)	H28G—C28C—H28I	109.5
C22B—N2B—C27C	119.3 (3)	H28H—C28C—H28I	109.5
O1A—C1A—C2A—C7A	−10.1 (3)	C7B—C2B—C3B—C4B	146.25 (16)
C6A—C1A—C2A—C7A	168.95 (16)	C1B—C2B—C3B—C4B	−30.2 (2)
O1A—C1A—C2A—C3A	169.52 (18)	C2B—C3B—C4B—C5B	58.33 (19)
C6A—C1A—C2A—C3A	−11.4 (2)	C3B—C4B—C5B—C6B	−55.76 (19)
C7A—C2A—C3A—C4A	157.03 (17)	O1B—C1B—C6B—C18B	0.5 (2)
C1A—C2A—C3A—C4A	−22.6 (2)	C2B—C1B—C6B—C18B	179.44 (14)
C2A—C3A—C4A—C5A	55.9 (2)	O1B—C1B—C6B—C5B	−176.45 (17)
C3A—C4A—C5A—C6A	−54.6 (2)	C2B—C1B—C6B—C5B	2.5 (2)
O1A—C1A—C6A—C18A	11.6 (3)	C4B—C5B—C6B—C18B	−151.37 (16)
C2A—C1A—C6A—C18A	−167.47 (15)	C4B—C5B—C6B—C1B	25.3 (2)
O1A—C1A—C6A—C5A	−168.42 (18)	C1B—C2B—C7B—C8B	176.79 (17)
C2A—C1A—C6A—C5A	12.5 (2)	C3B—C2B—C7B—C8B	0.3 (3)
C4A—C5A—C6A—C18A	−159.61 (16)	C2B—C7B—C8B—C9B	−158.56 (18)
C4A—C5A—C6A—C1A	20.4 (2)	C2B—C7B—C8B—C13B	22.1 (3)
C1A—C2A—C7A—C8A	178.15 (17)	C13B—C8B—C9B—C10B	−3.0 (3)
C3A—C2A—C7A—C8A	−1.5 (3)	C7B—C8B—C9B—C10B	177.63 (17)
C2A—C7A—C8A—C9A	−170.74 (19)	C8B—C9B—C10B—C11B	0.8 (3)
C2A—C7A—C8A—C13A	8.5 (3)	C14B—N1B—C11B—C10B	−8.2 (3)
C13A—C8A—C9A—C10A	−1.5 (3)	C16B—N1B—C11B—C10B	171.70 (17)
C7A—C8A—C9A—C10A	177.77 (17)	C16D—N1B—C11B—C10B	−142.2 (8)
C8A—C9A—C10A—C11A	0.1 (3)	C14B—N1B—C11B—C12B	172.86 (17)
C14A—N1A—C11A—C10A	−13.1 (3)	C16B—N1B—C11B—C12B	−7.3 (3)
C16A—N1A—C11A—C10A	176.3 (3)	C16D—N1B—C11B—C12B	38.8 (8)
C16C—N1A—C11A—C10A	−176.9 (4)	C9B—C10B—C11B—N1B	−176.91 (17)
C14A—N1A—C11A—C12A	164.16 (17)	C9B—C10B—C11B—C12B	2.1 (3)
C16A—N1A—C11A—C12A	−6.5 (4)	N1B—C11B—C12B—C13B	176.14 (17)
C16C—N1A—C11A—C12A	0.3 (4)	C10B—C11B—C12B—C13B	−2.9 (3)
C9A—C10A—C11A—N1A	178.25 (18)	C11B—C12B—C13B—C8B	0.7 (3)
C9A—C10A—C11A—C12A	0.8 (3)	C9B—C8B—C13B—C12B	2.2 (2)
N1A—C11A—C12A—C13A	−177.60 (18)	C7B—C8B—C13B—C12B	−178.47 (17)
C10A—C11A—C12A—C13A	−0.2 (3)	C11B—N1B—C14B—C15B	−72.2 (2)
C11A—C12A—C13A—C8A	−1.3 (3)	C16B—N1B—C14B—C15B	107.9 (2)
C9A—C8A—C13A—C12A	2.1 (3)	C16D—N1B—C14B—C15B	62.2 (7)
C7A—C8A—C13A—C12A	−177.07 (17)	C11B—N1B—C16B—C17B	100.7 (2)
C11A—N1A—C14A—C15A	88.9 (2)	C14B—N1B—C16B—C17B	−79.4 (2)
C16A—N1A—C14A—C15A	−100.3 (3)	C16D—N1B—C16B—C17B	13.4 (12)
C16C—N1A—C14A—C15A	−106.0 (3)	C11B—N1B—C16D—C17D	−125.3 (13)
C11A—N1A—C16A—C17A	−142.8 (4)	C14B—N1B—C16D—C17D	96.3 (15)
C14A—N1A—C16A—C17A	46.4 (6)	C16B—N1B—C16D—C17D	−10.5 (11)
C16C—N1A—C16A—C17A	100 (4)	C1B—C6B—C18B—C19B	−176.63 (16)
C11A—N1A—C16C—C17C	−99.2 (6)	C5B—C6B—C18B—C19B	0.2 (3)
C14A—N1A—C16C—C17C	96.2 (7)	C6B—C18B—C19B—C20B	−19.7 (3)
C16A—N1A—C16C—C17C	−33 (4)	C6B—C18B—C19B—C24B	160.84 (18)
C1A—C6A—C18A—C19A	179.32 (17)	C24B—C19B—C20B—C21B	−1.7 (2)
C5A—C6A—C18A—C19A	−0.7 (3)	C18B—C19B—C20B—C21B	178.90 (16)
C6A—C18A—C19A—C24A	170.53 (18)	C19B—C20B—C21B—C22B	−0.8 (3)
C6A—C18A—C19A—C20A	−10.2 (3)	C25B—N2B—C22B—C23B	−7.6 (3)
C24A—C19A—C20A—C21A	−2.7 (2)	C27C—N2B—C22B—C23B	−154.2 (3)
C18A—C19A—C20A—C21A	177.99 (16)	C27B—N2B—C22B—C23B	159.97 (17)
C19A—C20A—C21A—C22A	1.3 (3)	C25B—N2B—C22B—C21B	173.11 (18)
C27A—N2A—C22A—C21A	−6.2 (2)	C27C—N2B—C22B—C21B	26.5 (4)
C25A—N2A—C22A—C21A	175.41 (15)	C27B—N2B—C22B—C21B	−19.3 (3)
C27A—N2A—C22A—C23A	173.20 (16)	C20B—C21B—C22B—N2B	−178.57 (18)
C25A—N2A—C22A—C23A	−5.2 (2)	C20B—C21B—C22B—C23B	2.1 (3)
C20A—C21A—C22A—N2A	−179.71 (15)	N2B—C22B—C23B—C24B	179.84 (18)
C20A—C21A—C22A—C23A	0.9 (2)	C21B—C22B—C23B—C24B	−0.8 (3)
N2A—C22A—C23A—C24A	179.04 (16)	C22B—C23B—C24B—C19B	−1.8 (3)
C21A—C22A—C23A—C24A	−1.5 (2)	C20B—C19B—C24B—C23B	3.0 (3)
C22A—C23A—C24A—C19A	0.0 (3)	C18B—C19B—C24B—C23B	−177.49 (16)
C20A—C19A—C24A—C23A	2.1 (2)	C22B—N2B—C25B—C26B	87.2 (2)
C18A—C19A—C24A—C23A	−178.58 (16)	C27C—N2B—C25B—C26B	−123.8 (3)
C22A—N2A—C25A—C26A	90.0 (2)	C27B—N2B—C25B—C26B	−80.8 (2)
C27A—N2A—C25A—C26A	−88.5 (2)	C22B—N2B—C27B—C28B	99.5 (3)
C22A—N2A—C27A—C28A	90.5 (2)	C25B—N2B—C27B—C28B	−92.4 (2)
C25A—N2A—C27A—C28A	−91.0 (2)	C27C—N2B—C27B—C28B	−1.0 (5)
O1B—C1B—C2B—C7B	2.3 (2)	C22B—N2B—C27C—C28C	−102.5 (6)
C6B—C1B—C2B—C7B	−176.64 (15)	C25B—N2B—C27C—C28C	107.5 (6)
O1B—C1B—C2B—C3B	179.05 (17)	C27B—N2B—C27C—C28C	0.7 (4)
C6B—C1B—C2B—C3B	0.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C25B—H25B···O1A^i	0.99	2.55	3.479 (3)	156
C28B—H28B···O1A^i	0.98	2.57	3.542 (4)	171
C27C—H27C···O1A^i	0.99	2.53	3.505 (8)	169

Symmetry code: (i) x, y, z−1.