(E)-N,N-Diethyl-2,6-diisopropyl-4-[2-(4-nitro-phen-yl)ethen-yl]aniline.

The title compound, C24H32N2O2, was prepared by Horner olefination of 4-di-ethyl-amino-3,5-diiso-propyl-benzaldehyde and diethyl p-nitro-benzyl-phospho-nate. There are two independent mol-ecules (A and B) in the asymmetric unit. Their main axes, defined by the line connecting the N atoms of the nitro and amino groups, open an angle of 79.42 (3)°. Steric hindrance around the amino group is reflected in a long aryl C-N bond [1.434 (3) Å for mol-ecule A and 1.440 (3) Å for mol-ecule B], a pyramidal geometry [angle sum = 350.0 (2)° for mol-ecule A and 349.6 (2)° for mol-ecule B], and dihedral angles between the phenyl-ene group and the plane defined by the CH2-N-CH2 unit of 86.9 (3)° for mol-ecule A and 88.3 (3)° for mol-ecule B. This gives structural support for the electronic decoupling of the amino group from the nearly planar nitro-stilbene moiety (r.m.s. deviation for C, N and O atoms = 0.097 for mol-ecule A and 0.107 Å for mol-ecule B).

Related literature

For the synthesis of amino­nitro­stilbenes, see: Pfeiffer et al. (1915 ▶); Meier et al. (2004 ▶). For torsion-depent optical properties, see: Baumann et al. (1977 ▶); Wink & Detert (2013 ▶); Dekhtyar & Rettig (2007 ▶). For conjugated oligomers as sensing materials, see: Schmitt et al. (2008 ▶); Zucchero et al. (2009 ▶). For the structures of donor–acceptor stilbenoid dyes, see: Schollmeyer & Detert (2011 ▶); Fischer et al. (2011 ▶). For structures of sterically crowded push–pull analogues, see: Wink & Detert (2013 ▶). For the synthesis of the starting materiel, see: Wink et al. (2011 ▶). For chromophores and fluoro­phores based on quadrupolar donor–acceptor-substituted stilbenoid systems, see: Detert & Sugiono (2005 ▶); Schmitt et al. (2013 ▶); Nemkovich et al. (2010 ▶).

Experimental

Crystal data

C24H32N2O2

M = 380.52

Triclinic,

a = 7.3477 (7) Å

b = 15.4143 (14) Å

c = 20.3747 (19) Å

α = 104.642 (8)°

β = 92.414 (8)°

γ = 90.793 (7)°

V = 2230.0 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 193 K

0.60 × 0.10 × 0.05 mm

Data collection

Stoe IPDS 2T diffractometer

21656 measured reflections

10640 independent reflections

3887 reflections with I > 2σ(I)

R int = 0.086

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.174

S = 0.79

10640 reflections

518 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.24 e Å−3

Data collection: X-AREA (Stoe & Cie, 2011 ▶); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2011 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813030948/bt6943sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813030948/bt6943Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813030948/bt6943Isup3.cml

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

C24H32N2O2	Z = 4
Mr = 380.52	F(000) = 824
Triclinic, P1	Dx = 1.133 Mg m−3
Hall symbol: -P 1	Melting point: 408 K
a = 7.3477 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 15.4143 (14) Å	Cell parameters from 12450 reflections
c = 20.3747 (19) Å	θ = 2.6–27.5°
α = 104.642 (8)°	µ = 0.07 mm−1
β = 92.414 (8)°	T = 193 K
γ = 90.793 (7)°	Needle, yellow
V = 2230.0 (4) Å3	0.60 × 0.10 × 0.05 mm

Stoe IPDS 2T diffractometer	3887 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	Rint = 0.086
Plane graphite monochromator	θmax = 28.0°, θmin = 2.7°
Detector resolution: 6.67 pixels mm-1	h = −9→9
rotation method scans	k = −20→19
21656 measured reflections	l = 0→26
10640 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057	H-atom parameters constrained
wR(F2) = 0.174	w = 1/[σ2(Fo2) + (0.0886P)2] where P = (Fo2 + 2Fc2)/3
S = 0.79	(Δ/σ)max < 0.001
10640 reflections	Δρmax = 0.25 e Å−3
518 parameters	Δρmin = −0.24 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0087 (11)

Experimental. 1H-NMR (CDCl3): δ = 8.22 ("d", J = 8.8 Hz, 2 H, 3-H, 5-H, Ph—NO2); 7.64 ("d", J = 8.8 Hz, 2 H, 2-H, 6-H, Ph—NO2); 7.27 (d, J = 16.3 Hz, 1 H, vin); 7.27 (s, 2 H, 3-H, 5-H Ph); 7.08 (d, J = 16.3 Hz, 1 H, vin); 3.51 (sept, J = 6.9 Hz, 2 H, 2-H, i-prop); 3.09 (q, 4 H, NCH2); 1.23 (d, J = 6.9 Hz, 12 H,1-H, 3-H i-prop); 1.05 (t, J = 7.1 Hz, 6 C CH3 et) 1.27 (m, 12 H, CH2); 0.90 ("t", 6 H, CH3). 13C-NMR(CDCl3): δ = 150.4 (C-1, Ph), 146.9 (C-4 PhNO2), 146.7 (C-1 PhNO2), 144.5 (C-2, C-6 Ph), 134.0 (C-1 vin), 124.3 (C-2, C-6 PhNO2), 123.0 (C-3, C-5 PhNO2), 49.3 (NCH2), 28.0 (CH i-pr), 24.6 (CH3 i-pr), 15.4 (CH3 et). IR (ATR) 2959, 2931, 2871, 1633, 1590, 1512, 1457, 1336, 1186, 1105, 964, 862, 745, 6890 cm-1. HR-ESI-MS:found: 381.2545, calcd for (M+H+): 381.2542. UV-Vis: λ'max = 364 nm (cyclohexane); λ'max = 347 nm (toluene); λ'max = 344 nm, ε = 29304 l mol-1 cm-1 (dichloromethane); λ'max = 344 nm (acetonitrile).

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

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

	x	y	z	Uiso*/Ueq
C1	0.4949 (3)	0.30348 (17)	0.27877 (12)	0.0396 (6)
C2	0.5948 (4)	0.26657 (17)	0.22148 (13)	0.0422 (6)
H2	0.6339	0.2065	0.2140	0.051*
C3	0.6378 (3)	0.31579 (17)	0.17551 (13)	0.0410 (6)
C4	0.5801 (3)	0.40409 (17)	0.18589 (12)	0.0394 (6)
C5	0.4832 (3)	0.44422 (17)	0.24438 (13)	0.0412 (6)
C6	0.4431 (4)	0.39198 (17)	0.28856 (13)	0.0422 (6)
H6	0.3768	0.4181	0.3274	0.051*
C7	0.4422 (4)	0.25363 (18)	0.32733 (13)	0.0429 (6)
H7	0.3810	0.2859	0.3658	0.051*
C8	0.4714 (3)	0.16727 (18)	0.32324 (13)	0.0428 (6)
H8	0.5366	0.1356	0.2857	0.051*
C9	0.4133 (3)	0.11634 (17)	0.37066 (13)	0.0403 (6)
C10	0.3318 (4)	0.15621 (19)	0.43165 (14)	0.0499 (7)
H10	0.3172	0.2193	0.4443	0.060*
C11	0.2725 (4)	0.1049 (2)	0.47359 (15)	0.0554 (7)
H11	0.2174	0.1322	0.5148	0.067*
C12	0.2945 (4)	0.0136 (2)	0.45466 (14)	0.0475 (7)
C13	0.3759 (4)	−0.0285 (2)	0.39530 (15)	0.0512 (7)
H13	0.3913	−0.0915	0.3832	0.061*
C14	0.4338 (4)	0.02433 (18)	0.35431 (14)	0.0470 (7)
H14	0.4899	−0.0035	0.3134	0.056*
C15	0.7519 (4)	0.27354 (18)	0.11555 (13)	0.0469 (6)
H15	0.7405	0.3114	0.0824	0.056*
C16	0.9520 (4)	0.2754 (2)	0.13855 (17)	0.0641 (8)
H16A	0.9907	0.3371	0.1617	0.096*
H16B	1.0255	0.2536	0.0989	0.096*
H16C	0.9687	0.2369	0.1698	0.096*
C17	0.6881 (5)	0.1789 (2)	0.07859 (17)	0.0735 (10)
H17A	0.7058	0.1391	0.1088	0.110*
H17B	0.7587	0.1577	0.0381	0.110*
H17C	0.5586	0.1790	0.0650	0.110*
N18	0.6186 (3)	0.45126 (14)	0.13554 (11)	0.0433 (5)
C19	0.4644 (4)	0.4686 (2)	0.09364 (15)	0.0543 (7)
H19A	0.5098	0.4964	0.0585	0.065*
H19B	0.3838	0.5117	0.1224	0.065*
C20	0.3550 (4)	0.3842 (2)	0.05932 (16)	0.0628 (8)
H20A	0.4335	0.3415	0.0301	0.094*
H20B	0.2536	0.3992	0.0317	0.094*
H20C	0.3069	0.3571	0.0939	0.094*
C21	0.7607 (4)	0.5215 (2)	0.15235 (15)	0.0531 (7)
H21A	0.8299	0.5176	0.1942	0.064*
H21B	0.7035	0.5809	0.1614	0.064*
C22	0.8914 (5)	0.5135 (2)	0.09515 (18)	0.0709 (9)
H22A	0.9481	0.4548	0.0860	0.106*
H22B	0.9860	0.5609	0.1085	0.106*
H22C	0.8240	0.5197	0.0541	0.106*
C23	0.4226 (4)	0.54056 (18)	0.26072 (14)	0.0485 (7)
H23	0.4635	0.5677	0.2240	0.058*
C24	0.2156 (5)	0.5448 (2)	0.2612 (2)	0.0734 (10)
H24A	0.1723	0.5217	0.2985	0.110*
H24B	0.1624	0.5084	0.2179	0.110*
H24C	0.1790	0.6072	0.2675	0.110*
C25	0.5106 (5)	0.5954 (2)	0.32779 (16)	0.0707 (9)
H25A	0.4773	0.5685	0.3645	0.106*
H25B	0.4678	0.6570	0.3371	0.106*
H25C	0.6434	0.5958	0.3248	0.106*
N26	0.2300 (3)	−0.0413 (2)	0.49818 (15)	0.0605 (7)
O27	0.2465 (4)	−0.12263 (18)	0.48017 (13)	0.0808 (7)
O28	0.1604 (3)	−0.00304 (18)	0.55168 (12)	0.0764 (7)
C30	−0.0084 (3)	0.05172 (17)	0.27794 (13)	0.0409 (6)
C31	−0.0659 (4)	−0.03038 (17)	0.28669 (13)	0.0435 (6)
H31	−0.1336	−0.0312	0.3253	0.052*
C32	−0.0293 (3)	−0.11158 (17)	0.24173 (13)	0.0412 (6)
C33	0.0694 (3)	−0.11000 (16)	0.18411 (13)	0.0394 (6)
C34	0.1346 (3)	−0.02828 (17)	0.17470 (13)	0.0400 (6)
C35	0.0955 (3)	0.05126 (17)	0.22143 (13)	0.0421 (6)
H35	0.1400	0.1066	0.2150	0.050*
C36	−0.0575 (4)	0.13348 (18)	0.32684 (13)	0.0434 (6)
H36	−0.1172	0.1261	0.3656	0.052*
C37	−0.0280 (3)	0.21747 (18)	0.32317 (13)	0.0430 (6)
H37	0.0367	0.2249	0.2855	0.052*
C38	−0.0844 (3)	0.29959 (18)	0.37077 (13)	0.0419 (6)
C39	−0.0606 (4)	0.38122 (17)	0.35484 (14)	0.0464 (6)
H39	−0.0026	0.3826	0.3143	0.056*
C40	−0.1185 (4)	0.46049 (19)	0.39597 (14)	0.0509 (7)
H40	−0.1008	0.5158	0.3843	0.061*
C41	−0.2031 (4)	0.45700 (18)	0.45468 (14)	0.0474 (7)
C42	−0.2282 (4)	0.3779 (2)	0.47287 (15)	0.0563 (8)
H42	−0.2856	0.3774	0.5137	0.068*
C43	−0.1692 (4)	0.29890 (19)	0.43136 (14)	0.0513 (7)
H43	−0.1859	0.2440	0.4437	0.062*
C44	−0.0981 (4)	−0.19792 (18)	0.25670 (15)	0.0494 (7)
H44	−0.0614	−0.2491	0.2191	0.059*
C45	−0.3050 (4)	−0.2008 (2)	0.2578 (2)	0.0739 (10)
H45A	−0.3464	−0.2596	0.2623	0.111*
H45B	−0.3574	−0.1906	0.2154	0.111*
H45C	−0.3445	−0.1539	0.2963	0.111*
C46	−0.0117 (5)	−0.2105 (2)	0.32264 (17)	0.0732 (10)
H46A	−0.0399	−0.1594	0.3601	0.110*
H46B	0.1206	−0.2143	0.3190	0.110*
H46C	−0.0603	−0.2659	0.3313	0.110*
N47	0.1061 (3)	−0.19036 (14)	0.13296 (11)	0.0426 (5)
C48	0.2394 (4)	−0.25017 (19)	0.15094 (15)	0.0494 (7)
H48A	0.1751	−0.3007	0.1627	0.059*
H48B	0.3134	−0.2173	0.1916	0.059*
C49	0.3639 (5)	−0.2868 (2)	0.09384 (18)	0.0682 (9)
H49A	0.2937	−0.3266	0.0558	0.102*
H49B	0.4609	−0.3204	0.1099	0.102*
H49C	0.4178	−0.2370	0.0788	0.102*
C50	−0.0487 (4)	−0.23375 (19)	0.08914 (15)	0.0534 (7)
H50A	−0.1341	−0.2586	0.1164	0.064*
H50B	−0.0048	−0.2844	0.0535	0.064*
C51	−0.1488 (4)	−0.1704 (2)	0.05593 (16)	0.0600 (8)
H51A	−0.1947	−0.1208	0.0910	0.090*
H51B	−0.2512	−0.2026	0.0272	0.090*
H51C	−0.0656	−0.1467	0.0280	0.090*
C52	0.2523 (4)	−0.02585 (18)	0.11595 (13)	0.0454 (6)
H52	0.2337	−0.0848	0.0816	0.054*
C53	0.4520 (4)	−0.0174 (2)	0.13822 (17)	0.0643 (8)
H53A	0.4758	0.0401	0.1717	0.096*
H53B	0.5256	−0.0202	0.0988	0.096*
H53C	0.4841	−0.0665	0.1587	0.096*
C54	0.2021 (5)	0.0470 (2)	0.08046 (17)	0.0675 (9)
H54A	0.0725	0.0407	0.0663	0.101*
H54B	0.2751	0.0410	0.0405	0.101*
H54C	0.2264	0.1060	0.1118	0.101*
N55	−0.2667 (4)	0.54027 (19)	0.49826 (14)	0.0589 (7)
O56	−0.3403 (3)	0.53623 (16)	0.55103 (12)	0.0761 (7)
O57	−0.2477 (4)	0.60986 (16)	0.48113 (13)	0.0790 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0364 (13)	0.0449 (15)	0.0405 (13)	−0.0010 (11)	0.0036 (11)	0.0161 (11)
C2	0.0424 (14)	0.0391 (14)	0.0476 (15)	0.0048 (11)	0.0065 (12)	0.0150 (12)
C3	0.0399 (14)	0.0428 (15)	0.0423 (14)	0.0019 (11)	0.0037 (11)	0.0140 (12)
C4	0.0372 (13)	0.0448 (14)	0.0400 (13)	−0.0021 (11)	0.0037 (11)	0.0174 (11)
C5	0.0395 (14)	0.0431 (14)	0.0419 (14)	0.0014 (11)	0.0013 (11)	0.0125 (11)
C6	0.0421 (14)	0.0438 (15)	0.0423 (14)	0.0017 (11)	0.0039 (11)	0.0135 (12)
C7	0.0410 (14)	0.0481 (16)	0.0425 (14)	0.0015 (11)	0.0051 (11)	0.0164 (12)
C8	0.0386 (14)	0.0522 (17)	0.0401 (13)	−0.0007 (12)	0.0060 (11)	0.0160 (12)
C9	0.0339 (13)	0.0478 (15)	0.0428 (14)	0.0005 (11)	0.0035 (11)	0.0179 (12)
C10	0.0558 (17)	0.0504 (16)	0.0474 (16)	0.0062 (13)	0.0077 (13)	0.0186 (13)
C11	0.0573 (18)	0.068 (2)	0.0470 (16)	0.0048 (15)	0.0106 (14)	0.0234 (15)
C12	0.0405 (15)	0.0644 (19)	0.0469 (15)	−0.0022 (13)	0.0023 (12)	0.0313 (14)
C13	0.0504 (17)	0.0525 (17)	0.0565 (17)	0.0022 (13)	0.0057 (14)	0.0238 (14)
C14	0.0472 (16)	0.0493 (16)	0.0504 (16)	0.0068 (13)	0.0090 (13)	0.0222 (13)
C15	0.0517 (16)	0.0474 (16)	0.0460 (15)	0.0019 (13)	0.0136 (13)	0.0181 (12)
C16	0.0511 (18)	0.077 (2)	0.0655 (19)	0.0110 (16)	0.0166 (15)	0.0184 (17)
C17	0.088 (3)	0.062 (2)	0.063 (2)	−0.0143 (18)	0.0276 (19)	−0.0017 (16)
N18	0.0454 (13)	0.0452 (12)	0.0456 (12)	−0.0052 (10)	0.0013 (10)	0.0233 (10)
C19	0.0585 (18)	0.0606 (18)	0.0492 (16)	0.0001 (14)	−0.0021 (14)	0.0251 (14)
C20	0.0538 (18)	0.076 (2)	0.0578 (18)	−0.0047 (16)	−0.0032 (15)	0.0163 (16)
C21	0.0496 (16)	0.0509 (17)	0.0635 (18)	−0.0066 (13)	0.0020 (14)	0.0237 (14)
C22	0.067 (2)	0.073 (2)	0.083 (2)	−0.0051 (17)	0.0207 (18)	0.0356 (19)
C23	0.0504 (16)	0.0475 (16)	0.0509 (16)	0.0029 (13)	0.0074 (13)	0.0178 (13)
C24	0.061 (2)	0.061 (2)	0.106 (3)	0.0192 (17)	0.0203 (19)	0.032 (2)
C25	0.103 (3)	0.0473 (18)	0.0601 (19)	−0.0032 (18)	0.0006 (19)	0.0115 (15)
N26	0.0478 (15)	0.081 (2)	0.0655 (17)	−0.0073 (13)	−0.0017 (13)	0.0430 (16)
O27	0.0948 (19)	0.0746 (17)	0.0894 (18)	−0.0072 (14)	0.0134 (15)	0.0504 (14)
O28	0.0732 (16)	0.110 (2)	0.0594 (14)	−0.0038 (14)	0.0148 (12)	0.0438 (14)
C30	0.0378 (14)	0.0434 (15)	0.0426 (14)	−0.0004 (11)	0.0001 (11)	0.0133 (12)
C31	0.0418 (14)	0.0456 (15)	0.0462 (15)	0.0020 (12)	0.0076 (12)	0.0166 (12)
C32	0.0387 (14)	0.0416 (15)	0.0467 (14)	0.0006 (11)	0.0051 (11)	0.0172 (12)
C33	0.0390 (14)	0.0374 (14)	0.0419 (14)	0.0012 (11)	0.0042 (11)	0.0097 (11)
C34	0.0373 (14)	0.0423 (15)	0.0410 (14)	0.0009 (11)	0.0021 (11)	0.0119 (11)
C35	0.0405 (14)	0.0417 (15)	0.0468 (15)	−0.0015 (11)	0.0031 (12)	0.0162 (12)
C36	0.0415 (14)	0.0464 (16)	0.0428 (14)	0.0024 (12)	0.0048 (11)	0.0117 (12)
C37	0.0394 (14)	0.0477 (16)	0.0422 (14)	0.0038 (12)	0.0027 (11)	0.0113 (12)
C38	0.0353 (13)	0.0469 (15)	0.0427 (14)	0.0005 (11)	−0.0007 (11)	0.0105 (12)
C39	0.0483 (16)	0.0409 (15)	0.0484 (15)	0.0030 (12)	0.0057 (13)	0.0079 (12)
C40	0.0507 (17)	0.0450 (16)	0.0543 (17)	0.0005 (13)	0.0041 (14)	0.0074 (13)
C41	0.0443 (15)	0.0466 (16)	0.0439 (15)	0.0055 (12)	0.0016 (12)	−0.0023 (12)
C42	0.0598 (19)	0.0605 (19)	0.0441 (16)	0.0028 (15)	0.0105 (14)	0.0036 (14)
C43	0.0587 (18)	0.0492 (17)	0.0461 (15)	−0.0032 (14)	0.0076 (13)	0.0119 (13)
C44	0.0496 (16)	0.0440 (16)	0.0580 (17)	−0.0004 (12)	0.0095 (13)	0.0182 (13)
C45	0.0555 (19)	0.063 (2)	0.111 (3)	−0.0070 (16)	0.0199 (19)	0.034 (2)
C46	0.101 (3)	0.059 (2)	0.067 (2)	0.0040 (19)	0.001 (2)	0.0289 (17)
N47	0.0440 (12)	0.0370 (12)	0.0449 (12)	0.0012 (9)	−0.0009 (10)	0.0076 (9)
C48	0.0472 (16)	0.0462 (16)	0.0569 (17)	0.0052 (13)	0.0036 (13)	0.0166 (13)
C49	0.067 (2)	0.061 (2)	0.079 (2)	0.0191 (17)	0.0183 (18)	0.0189 (17)
C50	0.0536 (17)	0.0487 (16)	0.0535 (16)	−0.0061 (13)	−0.0026 (13)	0.0060 (13)
C51	0.0525 (18)	0.064 (2)	0.0614 (18)	0.0012 (15)	−0.0079 (15)	0.0133 (15)
C52	0.0513 (16)	0.0414 (15)	0.0449 (14)	0.0012 (12)	0.0120 (12)	0.0122 (12)
C53	0.0518 (18)	0.078 (2)	0.070 (2)	0.0060 (16)	0.0184 (16)	0.0281 (17)
C54	0.074 (2)	0.079 (2)	0.0608 (19)	0.0123 (18)	0.0169 (17)	0.0364 (17)
N55	0.0510 (15)	0.0601 (18)	0.0558 (16)	0.0056 (13)	−0.0056 (12)	−0.0026 (13)
O56	0.0750 (16)	0.0849 (17)	0.0544 (13)	0.0091 (13)	0.0146 (12)	−0.0105 (12)
O57	0.0921 (18)	0.0523 (14)	0.0835 (17)	0.0146 (13)	0.0113 (14)	−0.0014 (13)

C1—C6	1.389 (4)	C30—C31	1.385 (4)
C1—C2	1.405 (3)	C30—C35	1.406 (4)
C1—C7	1.458 (3)	C30—C36	1.456 (4)
C2—C3	1.389 (4)	C31—C32	1.389 (4)
C2—H2	0.9500	C31—H31	0.9500
C3—C4	1.398 (3)	C32—C33	1.411 (3)
C3—C15	1.523 (4)	C32—C44	1.523 (4)
C4—C5	1.421 (3)	C33—C34	1.402 (3)
C4—N18	1.434 (3)	C33—N47	1.440 (3)
C5—C6	1.388 (4)	C34—C35	1.391 (4)
C5—C23	1.515 (4)	C34—C52	1.514 (3)
C6—H6	0.9500	C35—H35	0.9500
C7—C8	1.333 (4)	C36—C37	1.331 (4)
C7—H7	0.9500	C36—H36	0.9500
C8—C9	1.463 (3)	C37—C38	1.464 (4)
C8—H8	0.9500	C37—H37	0.9500
C9—C14	1.384 (4)	C38—C39	1.387 (4)
C9—C10	1.402 (4)	C38—C43	1.408 (4)
C10—C11	1.382 (4)	C39—C40	1.380 (4)
C10—H10	0.9500	C39—H39	0.9500
C11—C12	1.375 (4)	C40—C41	1.384 (4)
C11—H11	0.9500	C40—H40	0.9500
C12—C13	1.384 (4)	C41—C42	1.374 (4)
C12—N26	1.460 (4)	C41—N55	1.459 (4)
C13—C14	1.380 (4)	C42—C43	1.382 (4)
C13—H13	0.9500	C42—H42	0.9500
C14—H14	0.9500	C43—H43	0.9500
C15—C17	1.520 (4)	C44—C46	1.519 (4)
C15—C16	1.522 (4)	C44—C45	1.522 (4)
C15—H15	1.0000	C44—H44	1.0000
C16—H16A	0.9800	C45—H45A	0.9800
C16—H16B	0.9800	C45—H45B	0.9800
C16—H16C	0.9800	C45—H45C	0.9800
C17—H17A	0.9800	C46—H46A	0.9800
C17—H17B	0.9800	C46—H46B	0.9800
C17—H17C	0.9800	C46—H46C	0.9800
N18—C19	1.458 (3)	N47—C48	1.452 (3)
N18—C21	1.460 (3)	N47—C50	1.459 (3)
C19—C20	1.514 (4)	C48—C49	1.510 (4)
C19—H19A	0.9900	C48—H48A	0.9900
C19—H19B	0.9900	C48—H48B	0.9900
C20—H20A	0.9800	C49—H49A	0.9800
C20—H20B	0.9800	C49—H49B	0.9800
C20—H20C	0.9800	C49—H49C	0.9800
C21—C22	1.523 (4)	C50—C51	1.504 (4)
C21—H21A	0.9900	C50—H50A	0.9900
C21—H21B	0.9900	C50—H50B	0.9900
C22—H22A	0.9800	C51—H51A	0.9800
C22—H22B	0.9800	C51—H51B	0.9800
C22—H22C	0.9800	C51—H51C	0.9800
C23—C24	1.523 (4)	C52—C53	1.511 (4)
C23—C25	1.525 (4)	C52—C54	1.522 (4)
C23—H23	1.0000	C52—H52	1.0000
C24—H24A	0.9800	C53—H53A	0.9800
C24—H24B	0.9800	C53—H53B	0.9800
C24—H24C	0.9800	C53—H53C	0.9800
C25—H25A	0.9800	C54—H54A	0.9800
C25—H25B	0.9800	C54—H54B	0.9800
C25—H25C	0.9800	C54—H54C	0.9800
N26—O27	1.223 (3)	N55—O57	1.217 (3)
N26—O28	1.236 (3)	N55—O56	1.239 (3)
C6—C1—C2	117.4 (2)	C31—C30—C35	117.5 (2)
C6—C1—C7	119.1 (2)	C31—C30—C36	119.1 (2)
C2—C1—C7	123.5 (2)	C35—C30—C36	123.4 (2)
C3—C2—C1	121.6 (2)	C30—C31—C32	123.1 (2)
C3—C2—H2	119.2	C30—C31—H31	118.5
C1—C2—H2	119.2	C32—C31—H31	118.5
C2—C3—C4	119.7 (2)	C31—C32—C33	118.3 (2)
C2—C3—C15	119.4 (2)	C31—C32—C44	118.6 (2)
C4—C3—C15	120.9 (2)	C33—C32—C44	123.1 (2)
C3—C4—C5	120.1 (2)	C34—C33—C32	120.2 (2)
C3—C4—N18	118.1 (2)	C34—C33—N47	117.5 (2)
C5—C4—N18	121.8 (2)	C32—C33—N47	122.3 (2)
C6—C5—C4	117.9 (2)	C35—C34—C33	119.4 (2)
C6—C5—C23	118.8 (2)	C35—C34—C52	119.7 (2)
C4—C5—C23	123.3 (2)	C33—C34—C52	120.9 (2)
C5—C6—C1	123.3 (2)	C34—C35—C30	121.5 (2)
C5—C6—H6	118.4	C34—C35—H35	119.2
C1—C6—H6	118.4	C30—C35—H35	119.2
C8—C7—C1	126.6 (2)	C37—C36—C30	127.1 (2)
C8—C7—H7	116.7	C37—C36—H36	116.4
C1—C7—H7	116.7	C30—C36—H36	116.4
C7—C8—C9	126.7 (2)	C36—C37—C38	127.2 (2)
C7—C8—H8	116.6	C36—C37—H37	116.4
C9—C8—H8	116.6	C38—C37—H37	116.4
C14—C9—C10	117.9 (2)	C39—C38—C43	118.2 (2)
C14—C9—C8	119.2 (2)	C39—C38—C37	119.3 (2)
C10—C9—C8	122.9 (2)	C43—C38—C37	122.5 (2)
C11—C10—C9	120.8 (3)	C40—C39—C38	122.1 (3)
C11—C10—H10	119.6	C40—C39—H39	118.9
C9—C10—H10	119.6	C38—C39—H39	118.9
C12—C11—C10	119.0 (3)	C39—C40—C41	118.0 (3)
C12—C11—H11	120.5	C39—C40—H40	121.0
C10—C11—H11	120.5	C41—C40—H40	121.0
C11—C12—C13	122.2 (2)	C42—C41—C40	121.9 (2)
C11—C12—N26	119.4 (3)	C42—C41—N55	119.5 (3)
C13—C12—N26	118.5 (3)	C40—C41—N55	118.5 (3)
C14—C13—C12	117.7 (3)	C41—C42—C43	119.5 (3)
C14—C13—H13	121.2	C41—C42—H42	120.2
C12—C13—H13	121.2	C43—C42—H42	120.2
C13—C14—C9	122.4 (3)	C42—C43—C38	120.2 (3)
C13—C14—H14	118.8	C42—C43—H43	119.9
C9—C14—H14	118.8	C38—C43—H43	119.9
C17—C15—C16	110.8 (3)	C46—C44—C45	111.0 (3)
C17—C15—C3	113.3 (2)	C46—C44—C32	111.4 (2)
C16—C15—C3	110.2 (2)	C45—C44—C32	111.2 (2)
C17—C15—H15	107.4	C46—C44—H44	107.7
C16—C15—H15	107.4	C45—C44—H44	107.7
C3—C15—H15	107.4	C32—C44—H44	107.7
C15—C16—H16A	109.5	C44—C45—H45A	109.5
C15—C16—H16B	109.5	C44—C45—H45B	109.5
H16A—C16—H16B	109.5	H45A—C45—H45B	109.5
C15—C16—H16C	109.5	C44—C45—H45C	109.5
H16A—C16—H16C	109.5	H45A—C45—H45C	109.5
H16B—C16—H16C	109.5	H45B—C45—H45C	109.5
C15—C17—H17A	109.5	C44—C46—H46A	109.5
C15—C17—H17B	109.5	C44—C46—H46B	109.5
H17A—C17—H17B	109.5	H46A—C46—H46B	109.5
C15—C17—H17C	109.5	C44—C46—H46C	109.5
H17A—C17—H17C	109.5	H46A—C46—H46C	109.5
H17B—C17—H17C	109.5	H46B—C46—H46C	109.5
C4—N18—C19	116.9 (2)	C33—N47—C48	117.2 (2)
C4—N18—C21	117.8 (2)	C33—N47—C50	116.5 (2)
C19—N18—C21	115.3 (2)	C48—N47—C50	115.8 (2)
N18—C19—C20	112.6 (2)	N47—C48—C49	112.1 (2)
N18—C19—H19A	109.1	N47—C48—H48A	109.2
C20—C19—H19A	109.1	C49—C48—H48A	109.2
N18—C19—H19B	109.1	N47—C48—H48B	109.2
C20—C19—H19B	109.1	C49—C48—H48B	109.2
H19A—C19—H19B	107.8	H48A—C48—H48B	107.9
C19—C20—H20A	109.5	C48—C49—H49A	109.5
C19—C20—H20B	109.5	C48—C49—H49B	109.5
H20A—C20—H20B	109.5	H49A—C49—H49B	109.5
C19—C20—H20C	109.5	C48—C49—H49C	109.5
H20A—C20—H20C	109.5	H49A—C49—H49C	109.5
H20B—C20—H20C	109.5	H49B—C49—H49C	109.5
N18—C21—C22	111.7 (3)	N47—C50—C51	112.6 (2)
N18—C21—H21A	109.3	N47—C50—H50A	109.1
C22—C21—H21A	109.3	C51—C50—H50A	109.1
N18—C21—H21B	109.3	N47—C50—H50B	109.1
C22—C21—H21B	109.3	C51—C50—H50B	109.1
H21A—C21—H21B	107.9	H50A—C50—H50B	107.8
C21—C22—H22A	109.5	C50—C51—H51A	109.5
C21—C22—H22B	109.5	C50—C51—H51B	109.5
H22A—C22—H22B	109.5	H51A—C51—H51B	109.5
C21—C22—H22C	109.5	C50—C51—H51C	109.5
H22A—C22—H22C	109.5	H51A—C51—H51C	109.5
H22B—C22—H22C	109.5	H51B—C51—H51C	109.5
C5—C23—C24	110.9 (2)	C53—C52—C34	111.0 (2)
C5—C23—C25	111.5 (2)	C53—C52—C54	110.3 (3)
C24—C23—C25	111.1 (3)	C34—C52—C54	113.8 (2)
C5—C23—H23	107.7	C53—C52—H52	107.1
C24—C23—H23	107.7	C34—C52—H52	107.1
C25—C23—H23	107.7	C54—C52—H52	107.1
C23—C24—H24A	109.5	C52—C53—H53A	109.5
C23—C24—H24B	109.5	C52—C53—H53B	109.5
H24A—C24—H24B	109.5	H53A—C53—H53B	109.5
C23—C24—H24C	109.5	C52—C53—H53C	109.5
H24A—C24—H24C	109.5	H53A—C53—H53C	109.5
H24B—C24—H24C	109.5	H53B—C53—H53C	109.5
C23—C25—H25A	109.5	C52—C54—H54A	109.5
C23—C25—H25B	109.5	C52—C54—H54B	109.5
H25A—C25—H25B	109.5	H54A—C54—H54B	109.5
C23—C25—H25C	109.5	C52—C54—H54C	109.5
H25A—C25—H25C	109.5	H54A—C54—H54C	109.5
H25B—C25—H25C	109.5	H54B—C54—H54C	109.5
O27—N26—O28	123.1 (3)	O57—N55—O56	123.0 (3)
O27—N26—C12	118.9 (3)	O57—N55—C41	119.2 (3)
O28—N26—C12	118.0 (3)	O56—N55—C41	117.8 (3)
C6—C1—C2—C3	−1.1 (4)	C35—C30—C31—C32	−1.5 (4)
C7—C1—C2—C3	178.2 (3)	C36—C30—C31—C32	178.4 (3)
C1—C2—C3—C4	−0.3 (4)	C30—C31—C32—C33	−0.8 (4)
C1—C2—C3—C15	177.9 (2)	C30—C31—C32—C44	179.5 (2)
C2—C3—C4—C5	2.1 (4)	C31—C32—C33—C34	2.7 (4)
C15—C3—C4—C5	−176.1 (2)	C44—C32—C33—C34	−177.6 (2)
C2—C3—C4—N18	−176.8 (2)	C31—C32—C33—N47	−176.9 (2)
C15—C3—C4—N18	5.0 (4)	C44—C32—C33—N47	2.8 (4)
C3—C4—C5—C6	−2.3 (4)	C32—C33—C34—C35	−2.2 (4)
N18—C4—C5—C6	176.5 (2)	N47—C33—C34—C35	177.3 (2)
C3—C4—C5—C23	177.5 (2)	C32—C33—C34—C52	175.5 (2)
N18—C4—C5—C23	−3.7 (4)	N47—C33—C34—C52	−4.9 (4)
C4—C5—C6—C1	0.9 (4)	C33—C34—C35—C30	−0.1 (4)
C23—C5—C6—C1	−179.0 (2)	C52—C34—C35—C30	−177.9 (2)
C2—C1—C6—C5	0.8 (4)	C31—C30—C35—C34	2.0 (4)
C7—C1—C6—C5	−178.5 (3)	C36—C30—C35—C34	−177.9 (2)
C6—C1—C7—C8	175.8 (3)	C31—C30—C36—C37	−173.6 (3)
C2—C1—C7—C8	−3.6 (4)	C35—C30—C36—C37	6.3 (4)
C1—C7—C8—C9	−177.8 (3)	C30—C36—C37—C38	177.1 (3)
C7—C8—C9—C14	171.6 (3)	C36—C37—C38—C39	−172.5 (3)
C7—C8—C9—C10	−6.4 (4)	C36—C37—C38—C43	4.8 (4)
C14—C9—C10—C11	−0.6 (4)	C43—C38—C39—C40	−0.5 (4)
C8—C9—C10—C11	177.4 (3)	C37—C38—C39—C40	176.9 (2)
C9—C10—C11—C12	0.0 (4)	C38—C39—C40—C41	−0.2 (4)
C10—C11—C12—C13	0.7 (4)	C39—C40—C41—C42	0.8 (4)
C10—C11—C12—N26	−179.2 (3)	C39—C40—C41—N55	−179.4 (2)
C11—C12—C13—C14	−0.7 (4)	C40—C41—C42—C43	−0.6 (5)
N26—C12—C13—C14	179.1 (3)	N55—C41—C42—C43	179.5 (3)
C12—C13—C14—C9	0.0 (4)	C41—C42—C43—C38	−0.1 (4)
C10—C9—C14—C13	0.6 (4)	C39—C38—C43—C42	0.7 (4)
C8—C9—C14—C13	−177.5 (3)	C37—C38—C43—C42	−176.7 (3)
C2—C3—C15—C17	46.7 (4)	C31—C32—C44—C46	−63.0 (3)
C4—C3—C15—C17	−135.1 (3)	C33—C32—C44—C46	117.4 (3)
C2—C3—C15—C16	−78.1 (3)	C31—C32—C44—C45	61.4 (3)
C4—C3—C15—C16	100.1 (3)	C33—C32—C44—C45	−118.3 (3)
C3—C4—N18—C19	109.1 (3)	C34—C33—N47—C48	108.3 (3)
C5—C4—N18—C19	−69.7 (3)	C32—C33—N47—C48	−72.1 (3)
C3—C4—N18—C21	−106.9 (3)	C34—C33—N47—C50	−108.3 (3)
C5—C4—N18—C21	74.3 (3)	C32—C33—N47—C50	71.3 (3)
C4—N18—C19—C20	−53.8 (3)	C33—N47—C48—C49	−138.5 (3)
C21—N18—C19—C20	161.4 (2)	C50—N47—C48—C49	77.8 (3)
C4—N18—C21—C22	133.2 (3)	C33—N47—C50—C51	53.3 (3)
C19—N18—C21—C22	−82.3 (3)	C48—N47—C50—C51	−162.7 (2)
C6—C5—C23—C24	−62.7 (3)	C35—C34—C52—C53	80.0 (3)
C4—C5—C23—C24	117.5 (3)	C33—C34—C52—C53	−97.7 (3)
C6—C5—C23—C25	61.6 (3)	C35—C34—C52—C54	−45.1 (4)
C4—C5—C23—C25	−118.2 (3)	C33—C34—C52—C54	137.1 (3)
C11—C12—N26—O27	178.4 (3)	C42—C41—N55—O57	−178.4 (3)
C13—C12—N26—O27	−1.5 (4)	C40—C41—N55—O57	1.7 (4)
C11—C12—N26—O28	−1.4 (4)	C42—C41—N55—O56	0.7 (4)
C13—C12—N26—O28	178.8 (3)	C40—C41—N55—O56	−179.2 (3)