4-(2-Benzoyl-benzoyl)-N,N-diphenyl-aniline.

The asymmetric unit of the title compound, C(32)H(23)NO(2), comprises two crystallographically independent mol-ecules. In both mol-ecules, the geometries about the N atoms deviate significantly from the ideal trigonal-planar geometry with bond-angle sums about the N atom of 359.32° in one mol-ecule and 359.86° in the other. The O atoms of the carbonyl groups are deviated significantly from the central benzene rings by 0.6747 (14) and -1.1223 (13) Å in one molecule and -0.6230 (13) and 1.1559 (12) Å in the other. In the diphenyl-aniline units, the terminal phenyl rings are almost orthogonal to each other, with dihedral angles of 89.79 (9) and 89.76 (9)°. The crystal structure features C-H⋯O and C-H⋯π inter-actions.

Related literature

For the biological importance and usage of diketones, see: Sugawara et al. (2001 ▶); Kennedy et al. (2002 ▶); Song et al. (2006 ▶); Kakimoto et al. (2008 ▶). For related structures, see: Narayanan et al. (2011 ▶); Wu et al. (2011 ▶).

Experimental

Crystal data

C32H23NO2

M = 453.51

Triclinic,

a = 10.7599 (3) Å

b = 13.0389 (3) Å

c = 17.9453 (5) Å

α = 90.447 (2)°

β = 98.415 (2)°

γ = 108.904 (2)°

V = 2352.13 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.977, T max = 0.984

39694 measured reflections

8280 independent reflections

6006 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.097

S = 1.01

8280 reflections

631 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT (Bruker, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681202466X/rk2362sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202466X/rk2362Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681202466X/rk2362Isup3.cml

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

C32H23NO2	Z = 4
Mr = 453.51	F(000) = 952
Triclinic, P1	Dx = 1.281 Mg m−3
Hall symbol: -P 1	Melting point = 447–448 K
a = 10.7599 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.0389 (3) Å	Cell parameters from 8280 reflections
c = 17.9453 (5) Å	θ = 1.2–25.0°
α = 90.447 (2)°	µ = 0.08 mm−1
β = 98.415 (2)°	T = 295 K
γ = 108.904 (2)°	Block, yellow
V = 2352.13 (11) Å3	0.30 × 0.25 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	8280 independent reflections
Radiation source: fine-focus sealed tube	6006 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ & ω scans	θmax = 25.0°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→12
Tmin = 0.977, Tmax = 0.984	k = −15→15
39694 measured reflections	l = −21→21

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0402P)2 + 0.4791P] where P = (Fo2 + 2Fc2)/3
8280 reflections	(Δ/σ)max < 0.001
631 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.27625 (16)	0.07397 (12)	0.07392 (9)	0.0430 (4)
C1'	0.69995 (15)	0.41476 (12)	0.42657 (9)	0.0438 (4)
C2	0.36460 (18)	0.08266 (14)	0.02410 (10)	0.0551 (4)
H2	0.4403	0.1438	0.0279	0.066*
C2'	0.60717 (17)	0.36678 (14)	0.47244 (10)	0.0570 (4)
H2'	0.5282	0.3826	0.4678	0.068*
C3	0.34265 (19)	0.00215 (14)	−0.03134 (10)	0.0603 (5)
H3	0.4038	0.0089	−0.0642	0.072*
C3'	0.62992 (19)	0.29579 (15)	0.52498 (11)	0.0629 (5)
H3'	0.5659	0.2634	0.5549	0.076*
C4'	0.74661 (19)	0.27278 (14)	0.53322 (10)	0.0581 (5)
H4'	0.7624	0.2254	0.5690	0.070*
C4	0.23104 (19)	−0.08763 (14)	−0.03807 (10)	0.0579 (5)
H4	0.2158	−0.1417	−0.0757	0.069*
C5'	0.84025 (17)	0.32012 (12)	0.48821 (9)	0.0489 (4)
H5'	0.9196	0.3048	0.4942	0.059*
C5	0.14133 (17)	−0.09762 (13)	0.01107 (9)	0.0510 (4)
H5	0.0655	−0.1587	0.0062	0.061*
C6	0.16218 (15)	−0.01811 (12)	0.06770 (8)	0.0425 (4)
C6'	0.81831 (15)	0.39033 (11)	0.43398 (8)	0.0412 (4)
C7'	0.92194 (16)	0.44636 (13)	0.38769 (9)	0.0459 (4)
C7	0.06076 (16)	−0.02446 (13)	0.11750 (9)	0.0465 (4)
C8'	1.01657 (15)	0.39358 (12)	0.36670 (8)	0.0429 (4)
C8	−0.02619 (15)	−0.13156 (12)	0.13754 (8)	0.0436 (4)
C9	0.01631 (17)	−0.22103 (13)	0.14645 (9)	0.0495 (4)
H9	0.0995	−0.2173	0.1356	0.059*
C9'	0.98162 (17)	0.28211 (13)	0.35386 (9)	0.0500 (4)
H9'	0.8988	0.2370	0.3625	0.060*
C10'	1.0691 (2)	0.23776 (16)	0.32837 (10)	0.0632 (5)
H10'	1.0440	0.1631	0.3186	0.076*
C10	−0.0645 (2)	−0.31547 (14)	0.17138 (10)	0.0625 (5)
H10	−0.0346	−0.3746	0.1784	0.075*
C11'	1.1919 (2)	0.30246 (19)	0.31746 (11)	0.0741 (6)
H11'	1.2506	0.2720	0.3006	0.089*
C11	−0.1883 (2)	−0.32275 (16)	0.18595 (12)	0.0725 (6)
H11	−0.2423	−0.3867	0.2028	0.087*
C12'	1.2291 (2)	0.41293 (19)	0.33146 (12)	0.0736 (6)
H12'	1.3136	0.4570	0.3250	0.088*
C12	−0.2329 (2)	−0.23545 (17)	0.17560 (11)	0.0712 (5)
H12	−0.3179	−0.2408	0.1841	0.085*
C13'	1.14175 (18)	0.45860 (15)	0.35504 (10)	0.0586 (5)
H13'	1.1668	0.5336	0.3632	0.070*
C13	−0.15126 (18)	−0.14003 (15)	0.15261 (10)	0.0574 (4)
H13	−0.1808	−0.0805	0.1472	0.069*
C14'	0.66441 (16)	0.48548 (13)	0.36702 (9)	0.0482 (4)
C14	0.31268 (15)	0.16201 (12)	0.13560 (9)	0.0448 (4)
C15	0.31416 (14)	0.27125 (11)	0.11440 (8)	0.0391 (3)
C15'	0.67316 (14)	0.59654 (12)	0.38928 (8)	0.0403 (3)
C16	0.38144 (15)	0.36045 (12)	0.16431 (8)	0.0433 (4)
H16	0.4286	0.3509	0.2099	0.052*
C16'	0.61718 (15)	0.65595 (12)	0.33932 (8)	0.0444 (4)
H16'	0.5685	0.6226	0.2933	0.053*
C17'	0.63145 (15)	0.76188 (12)	0.35563 (8)	0.0438 (4)
H17'	0.5914	0.7990	0.3212	0.053*
C17	0.37950 (16)	0.46233 (12)	0.14749 (8)	0.0458 (4)
H17	0.4279	0.5211	0.1811	0.055*
C18'	0.70580 (14)	0.81510 (12)	0.42364 (8)	0.0382 (3)
C18	0.30607 (15)	0.47927 (11)	0.08079 (8)	0.0410 (4)
C19	0.24269 (16)	0.39050 (12)	0.02941 (8)	0.0455 (4)
H19	0.1964	0.4000	−0.0166	0.055*
C19'	0.75877 (15)	0.75522 (12)	0.47512 (8)	0.0415 (4)
H19'	0.8059	0.7880	0.5216	0.050*
C20'	0.74238 (15)	0.64827 (12)	0.45818 (8)	0.0422 (4)
H20'	0.7783	0.6097	0.4936	0.051*
C20	0.24795 (15)	0.28909 (12)	0.04605 (8)	0.0440 (4)
H20	0.2062	0.2312	0.0107	0.053*
C21'	0.70246 (16)	0.99230 (12)	0.37988 (8)	0.0435 (4)
C21	0.31513 (16)	0.66186 (12)	0.12420 (8)	0.0439 (4)
C22'	0.76141 (18)	0.99793 (13)	0.31616 (9)	0.0528 (4)
H22'	0.8188	0.9589	0.3117	0.063*
C22	0.26337 (18)	0.63550 (13)	0.18995 (9)	0.0534 (4)
H22	0.2146	0.5639	0.1968	0.064*
C23'	0.7352 (2)	1.06155 (14)	0.25908 (10)	0.0630 (5)
H23'	0.7741	1.0645	0.2158	0.076*
C23	0.2839 (2)	0.71546 (16)	0.24576 (10)	0.0632 (5)
H23	0.2505	0.6970	0.2905	0.076*
C24	0.35260 (19)	0.82138 (15)	0.23590 (10)	0.0616 (5)
H24	0.3664	0.8747	0.2738	0.074*
C24'	0.6521 (2)	1.12055 (14)	0.26564 (11)	0.0652 (5)
H24'	0.6339	1.1627	0.2267	0.078*
C25	0.40083 (18)	0.84821 (14)	0.17000 (11)	0.0637 (5)
H25	0.4460	0.9204	0.1625	0.076*
C25'	0.59638 (18)	1.11734 (15)	0.32946 (12)	0.0639 (5)
H25'	0.5418	1.1588	0.3345	0.077*
C26	0.38310 (18)	0.76933 (13)	0.11457 (10)	0.0575 (4)
H26	0.4173	0.7885	0.0701	0.069*
C26'	0.62057 (17)	1.05289 (13)	0.38663 (10)	0.0543 (4)
H26'	0.5815	1.0504	0.4298	0.065*
C27	0.24811 (17)	0.60229 (11)	−0.00952 (8)	0.0443 (4)
C27'	0.77752 (15)	0.97481 (12)	0.51332 (8)	0.0411 (4)
C28	0.12612 (18)	0.61642 (13)	−0.02520 (9)	0.0527 (4)
H28	0.0764	0.6150	0.0133	0.063*
C28'	0.89213 (16)	1.06300 (13)	0.52478 (9)	0.0476 (4)
H28'	0.9353	1.0901	0.4843	0.057*
C29'	0.94322 (17)	1.11138 (15)	0.59632 (10)	0.0575 (4)
H29'	1.0202	1.1716	0.6039	0.069*
C29	0.0772 (2)	0.63275 (14)	−0.09784 (11)	0.0644 (5)
H29	−0.0054	0.6424	−0.1085	0.077*
C30'	0.88069 (19)	1.07092 (16)	0.65619 (10)	0.0601 (5)
H30'	0.9159	1.1032	0.7044	0.072*
C30	0.1508 (2)	0.63475 (15)	−0.15438 (10)	0.0679 (5)
H30	0.1176	0.6451	−0.2035	0.081*
C31	0.2729 (2)	0.62168 (15)	−0.13894 (10)	0.0669 (5)
H31	0.3226	0.6237	−0.1775	0.080*
C31'	0.7665 (2)	0.98309 (15)	0.64515 (9)	0.0597 (5)
H31'	0.7243	0.9556	0.6859	0.072*
C32	0.32234 (19)	0.60559 (13)	−0.06637 (9)	0.0560 (4)
H32	0.4055	0.5970	−0.0558	0.067*
C32'	0.71396 (18)	0.93544 (13)	0.57353 (9)	0.0520 (4)
H32'	0.6355	0.8766	0.5659	0.062*
O1	0.04810 (13)	0.05895 (10)	0.14103 (8)	0.0695 (4)
O1'	0.92974 (13)	0.53640 (10)	0.36682 (8)	0.0748 (4)
O2	0.34835 (13)	0.14309 (9)	0.20021 (7)	0.0654 (3)
N1'	0.72530 (14)	0.92462 (10)	0.43903 (7)	0.0465 (3)
N1	0.29685 (15)	0.58160 (10)	0.06558 (7)	0.0504 (3)
O2'	0.62324 (14)	0.44734 (10)	0.30249 (7)	0.0770 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0507 (9)	0.0387 (8)	0.0430 (9)	0.0204 (7)	0.0050 (7)	0.0086 (7)
C1'	0.0452 (9)	0.0360 (8)	0.0457 (9)	0.0095 (7)	0.0024 (7)	−0.0081 (7)
C2	0.0590 (11)	0.0474 (10)	0.0607 (11)	0.0168 (8)	0.0166 (9)	0.0086 (8)
C2'	0.0483 (10)	0.0553 (10)	0.0674 (12)	0.0154 (8)	0.0129 (9)	−0.0037 (9)
C3	0.0748 (13)	0.0558 (11)	0.0598 (11)	0.0273 (10)	0.0263 (10)	0.0100 (9)
C3'	0.0676 (12)	0.0557 (11)	0.0665 (12)	0.0127 (9)	0.0307 (10)	0.0049 (9)
C4'	0.0753 (13)	0.0519 (10)	0.0533 (11)	0.0240 (9)	0.0222 (9)	0.0096 (8)
C4	0.0825 (13)	0.0497 (10)	0.0468 (10)	0.0271 (10)	0.0152 (9)	0.0020 (8)
C5'	0.0567 (10)	0.0477 (9)	0.0471 (9)	0.0220 (8)	0.0116 (8)	0.0020 (8)
C5	0.0605 (11)	0.0432 (9)	0.0475 (10)	0.0155 (8)	0.0064 (8)	0.0029 (7)
C6	0.0490 (9)	0.0393 (8)	0.0410 (8)	0.0188 (7)	0.0026 (7)	0.0066 (7)
C6'	0.0453 (9)	0.0348 (8)	0.0409 (8)	0.0102 (7)	0.0052 (7)	−0.0045 (6)
C7'	0.0491 (10)	0.0406 (9)	0.0445 (9)	0.0113 (7)	0.0044 (7)	0.0011 (7)
C7	0.0508 (10)	0.0475 (9)	0.0428 (9)	0.0210 (8)	0.0011 (7)	0.0000 (7)
C8'	0.0469 (9)	0.0474 (9)	0.0332 (8)	0.0141 (7)	0.0059 (7)	0.0049 (7)
C8	0.0479 (9)	0.0479 (9)	0.0341 (8)	0.0161 (7)	0.0033 (7)	−0.0014 (7)
C9	0.0500 (10)	0.0489 (9)	0.0485 (10)	0.0159 (8)	0.0053 (8)	0.0007 (7)
C9'	0.0503 (10)	0.0523 (10)	0.0471 (9)	0.0161 (8)	0.0081 (8)	0.0013 (8)
C10'	0.0751 (13)	0.0627 (11)	0.0629 (12)	0.0333 (10)	0.0212 (10)	0.0054 (9)
C10	0.0741 (13)	0.0480 (10)	0.0661 (12)	0.0175 (9)	0.0192 (10)	0.0059 (9)
C11'	0.0813 (15)	0.0951 (16)	0.0700 (13)	0.0506 (13)	0.0364 (11)	0.0240 (12)
C11	0.0792 (14)	0.0586 (12)	0.0743 (14)	0.0061 (10)	0.0329 (11)	0.0056 (10)
C12'	0.0585 (12)	0.0921 (16)	0.0763 (14)	0.0228 (11)	0.0333 (10)	0.0268 (12)
C12	0.0614 (12)	0.0806 (14)	0.0742 (14)	0.0183 (11)	0.0303 (10)	0.0065 (11)
C13'	0.0593 (11)	0.0573 (11)	0.0570 (11)	0.0116 (9)	0.0186 (9)	0.0129 (9)
C13	0.0610 (11)	0.0670 (12)	0.0519 (10)	0.0289 (10)	0.0151 (9)	0.0034 (9)
C14'	0.0462 (9)	0.0483 (9)	0.0460 (10)	0.0147 (7)	−0.0029 (8)	−0.0092 (8)
C14	0.0461 (9)	0.0455 (9)	0.0425 (9)	0.0164 (7)	0.0031 (7)	0.0065 (7)
C15	0.0414 (8)	0.0401 (8)	0.0355 (8)	0.0139 (7)	0.0036 (7)	0.0016 (6)
C15'	0.0407 (8)	0.0421 (8)	0.0369 (8)	0.0135 (7)	0.0026 (7)	−0.0013 (7)
C16	0.0464 (9)	0.0482 (9)	0.0335 (8)	0.0158 (7)	−0.0003 (7)	0.0011 (7)
C16'	0.0437 (9)	0.0510 (9)	0.0337 (8)	0.0140 (7)	−0.0050 (7)	−0.0063 (7)
C17'	0.0455 (9)	0.0510 (9)	0.0371 (8)	0.0216 (7)	0.0004 (7)	0.0036 (7)
C17	0.0539 (10)	0.0408 (9)	0.0370 (8)	0.0117 (7)	−0.0013 (7)	−0.0062 (7)
C18'	0.0403 (8)	0.0428 (8)	0.0340 (8)	0.0166 (7)	0.0070 (7)	0.0012 (6)
C18	0.0523 (9)	0.0369 (8)	0.0338 (8)	0.0142 (7)	0.0082 (7)	0.0017 (6)
C19	0.0597 (10)	0.0425 (9)	0.0322 (8)	0.0185 (8)	−0.0036 (7)	0.0005 (7)
C19'	0.0476 (9)	0.0442 (9)	0.0309 (8)	0.0159 (7)	−0.0012 (7)	−0.0033 (6)
C20'	0.0465 (9)	0.0442 (9)	0.0363 (8)	0.0179 (7)	0.0008 (7)	0.0022 (7)
C20	0.0528 (10)	0.0388 (8)	0.0366 (8)	0.0138 (7)	−0.0016 (7)	−0.0035 (6)
C21'	0.0526 (10)	0.0406 (8)	0.0366 (8)	0.0169 (7)	0.0008 (7)	0.0006 (7)
C21	0.0553 (10)	0.0385 (8)	0.0377 (9)	0.0166 (7)	0.0043 (7)	−0.0005 (7)
C22'	0.0698 (12)	0.0496 (10)	0.0429 (9)	0.0244 (9)	0.0103 (8)	0.0035 (8)
C22	0.0739 (12)	0.0447 (9)	0.0440 (10)	0.0209 (8)	0.0137 (9)	0.0044 (7)
C23'	0.0873 (14)	0.0550 (11)	0.0402 (10)	0.0154 (10)	0.0084 (9)	0.0052 (8)
C23	0.0924 (14)	0.0686 (12)	0.0409 (10)	0.0421 (11)	0.0132 (9)	0.0027 (9)
C24	0.0715 (12)	0.0608 (12)	0.0541 (11)	0.0329 (10)	−0.0100 (10)	−0.0186 (9)
C24'	0.0757 (13)	0.0506 (11)	0.0575 (12)	0.0139 (10)	−0.0115 (10)	0.0136 (9)
C25	0.0646 (12)	0.0419 (10)	0.0759 (14)	0.0084 (8)	0.0050 (10)	−0.0105 (9)
C25'	0.0594 (12)	0.0579 (11)	0.0772 (14)	0.0279 (9)	−0.0012 (10)	0.0115 (10)
C26	0.0668 (12)	0.0451 (10)	0.0573 (11)	0.0106 (8)	0.0177 (9)	0.0001 (8)
C26'	0.0586 (11)	0.0561 (10)	0.0527 (10)	0.0251 (9)	0.0088 (8)	0.0059 (8)
C27	0.0648 (11)	0.0332 (8)	0.0345 (8)	0.0153 (7)	0.0086 (8)	0.0032 (6)
C27'	0.0525 (10)	0.0424 (8)	0.0346 (8)	0.0240 (8)	0.0072 (7)	0.0008 (7)
C28	0.0630 (11)	0.0455 (9)	0.0478 (10)	0.0135 (8)	0.0134 (8)	0.0026 (7)
C28'	0.0509 (10)	0.0533 (10)	0.0428 (9)	0.0214 (8)	0.0111 (8)	0.0030 (7)
C29'	0.0522 (11)	0.0628 (11)	0.0547 (11)	0.0186 (9)	0.0009 (9)	−0.0072 (9)
C29	0.0694 (13)	0.0588 (11)	0.0590 (12)	0.0190 (9)	−0.0036 (10)	0.0039 (9)
C30'	0.0732 (13)	0.0727 (12)	0.0380 (9)	0.0338 (11)	−0.0020 (9)	−0.0102 (9)
C30	0.1006 (17)	0.0564 (11)	0.0393 (10)	0.0214 (11)	−0.0027 (10)	0.0063 (8)
C31	0.1025 (16)	0.0615 (12)	0.0424 (10)	0.0288 (11)	0.0252 (11)	0.0113 (9)
C31'	0.0840 (14)	0.0646 (11)	0.0393 (9)	0.0314 (11)	0.0213 (9)	0.0038 (8)
C32	0.0708 (12)	0.0565 (10)	0.0481 (10)	0.0271 (9)	0.0178 (9)	0.0086 (8)
C32'	0.0621 (11)	0.0493 (9)	0.0459 (10)	0.0165 (8)	0.0165 (8)	−0.0007 (8)
O1	0.0785 (9)	0.0500 (7)	0.0888 (10)	0.0270 (6)	0.0279 (7)	−0.0009 (6)
O1'	0.0829 (9)	0.0524 (8)	0.1026 (11)	0.0291 (7)	0.0401 (8)	0.0267 (7)
O2	0.0882 (9)	0.0573 (7)	0.0477 (7)	0.0266 (7)	−0.0055 (7)	0.0105 (6)
N1'	0.0667 (9)	0.0435 (7)	0.0328 (7)	0.0252 (7)	0.0032 (6)	0.0005 (6)
N1	0.0808 (10)	0.0384 (7)	0.0340 (7)	0.0233 (7)	0.0067 (7)	0.0010 (5)
O2'	0.1054 (11)	0.0661 (8)	0.0536 (8)	0.0357 (8)	−0.0215 (7)	−0.0226 (6)

C1—C2	1.377 (2)	C17'—C18'	1.397 (2)
C1—C6	1.401 (2)	C17'—H17'	0.9300
C1—C14	1.503 (2)	C17—C18	1.395 (2)
C1'—C2'	1.382 (2)	C17—H17	0.9300
C1'—C6'	1.398 (2)	C18'—C19'	1.391 (2)
C1'—C14'	1.504 (2)	C18'—N1'	1.3936 (18)
C2—C3	1.379 (2)	C18—C19	1.394 (2)
C2—H2	0.9300	C18—N1	1.3957 (18)
C2'—C3'	1.378 (3)	C19—C20	1.375 (2)
C2'—H2'	0.9300	C19—H19	0.9300
C3—C4	1.368 (2)	C19'—C20'	1.373 (2)
C3—H3	0.9300	C19'—H19'	0.9300
C3'—C4'	1.371 (3)	C20'—H20'	0.9300
C3'—H3'	0.9300	C20—H20	0.9300
C4'—C5'	1.375 (2)	C21'—C26'	1.377 (2)
C4'—H4'	0.9300	C21'—C22'	1.378 (2)
C4—C5	1.377 (2)	C21'—N1'	1.4299 (19)
C4—H4	0.9300	C21—C22	1.377 (2)
C5'—C6'	1.388 (2)	C21—C26	1.380 (2)
C5'—H5'	0.9300	C21—N1	1.4246 (18)
C5—C6	1.387 (2)	C22'—C23'	1.377 (2)
C5—H5	0.9300	C22'—H22'	0.9300
C6—C7	1.491 (2)	C22—C23	1.382 (2)
C6'—C7'	1.490 (2)	C22—H22	0.9300
C7'—O1'	1.2158 (18)	C23'—C24'	1.370 (3)
C7'—C8'	1.488 (2)	C23'—H23'	0.9300
C7—O1	1.2187 (18)	C23—C24	1.366 (3)
C7—C8	1.488 (2)	C23—H23	0.9300
C8'—C13'	1.386 (2)	C24—C25	1.363 (3)
C8'—C9'	1.386 (2)	C24—H24	0.9300
C8—C13	1.381 (2)	C24'—C25'	1.364 (3)
C8—C9	1.387 (2)	C24'—H24'	0.9300
C9—C10	1.379 (2)	C25—C26	1.373 (2)
C9—H9	0.9300	C25—H25	0.9300
C9'—C10'	1.380 (2)	C25'—C26'	1.380 (2)
C9'—H9'	0.9300	C25'—H25'	0.9300
C10'—C11'	1.361 (3)	C26—H26	0.9300
C10'—H10'	0.9300	C26'—H26'	0.9300
C10—C11	1.369 (3)	C27—C28	1.373 (2)
C10—H10	0.9300	C27—C32	1.377 (2)
C11'—C12'	1.375 (3)	C27—N1	1.4335 (19)
C11'—H11'	0.9300	C27'—C28'	1.374 (2)
C11—C12	1.375 (3)	C27'—C32'	1.377 (2)
C11—H11	0.9300	C27'—N1'	1.4318 (18)
C12'—C13'	1.375 (3)	C28—C29	1.378 (2)
C12'—H12'	0.9300	C28—H28	0.9300
C12—C13	1.377 (3)	C28'—C29'	1.380 (2)
C12—H12	0.9300	C28'—H28'	0.9300
C13'—H13'	0.9300	C29'—C30'	1.370 (2)
C13—H13	0.9300	C29'—H29'	0.9300
C14'—O2'	1.2177 (18)	C29—C30	1.371 (3)
C14'—C15'	1.469 (2)	C29—H29	0.9300
C14—O2	1.2200 (18)	C30'—C31'	1.369 (3)
C14—C15	1.473 (2)	C30'—H30'	0.9300
C15—C20	1.386 (2)	C30—C31	1.367 (3)
C15—C16	1.388 (2)	C30—H30	0.9300
C15'—C16'	1.386 (2)	C31—C32	1.377 (2)
C15'—C20'	1.390 (2)	C31—H31	0.9300
C16—C17	1.371 (2)	C31'—C32'	1.380 (2)
C16—H16	0.9300	C31'—H31'	0.9300
C16'—C17'	1.364 (2)	C32—H32	0.9300
C16'—H16'	0.9300	C32'—H32'	0.9300
C2—C1—C6	119.21 (14)	C16—C17—C18	121.08 (14)
C2—C1—C14	117.34 (14)	C16—C17—H17	119.5
C6—C1—C14	123.34 (14)	C18—C17—H17	119.5
C2'—C1'—C6'	119.08 (15)	C19'—C18'—N1'	121.44 (13)
C2'—C1'—C14'	117.98 (15)	C19'—C18'—C17'	117.87 (13)
C6'—C1'—C14'	122.82 (15)	N1'—C18'—C17'	120.68 (13)
C1—C2—C3	121.03 (16)	C19—C18—C17	117.71 (13)
C1—C2—H2	119.5	C19—C18—N1	120.97 (13)
C3—C2—H2	119.5	C17—C18—N1	121.32 (13)
C3'—C2'—C1'	120.97 (16)	C20—C19—C18	120.62 (14)
C3'—C2'—H2'	119.5	C20—C19—H19	119.7
C1'—C2'—H2'	119.5	C18—C19—H19	119.7
C4—C3—C2	120.08 (17)	C20'—C19'—C18'	120.80 (13)
C4—C3—H3	120.0	C20'—C19'—H19'	119.6
C2—C3—H3	120.0	C18'—C19'—H19'	119.6
C4'—C3'—C2'	120.18 (17)	C19'—C20'—C15'	121.35 (14)
C4'—C3'—H3'	119.9	C19'—C20'—H20'	119.3
C2'—C3'—H3'	119.9	C15'—C20'—H20'	119.3
C3'—C4'—C5'	119.61 (17)	C19—C20—C15	121.48 (14)
C3'—C4'—H4'	120.2	C19—C20—H20	119.3
C5'—C4'—H4'	120.2	C15—C20—H20	119.3
C3—C4—C5	119.73 (16)	C26'—C21'—C22'	119.43 (15)
C3—C4—H4	120.1	C26'—C21'—N1'	119.62 (14)
C5—C4—H4	120.1	C22'—C21'—N1'	120.94 (14)
C4'—C5'—C6'	121.15 (16)	C22—C21—C26	118.69 (14)
C4'—C5'—H5'	119.4	C22—C21—N1	121.61 (14)
C6'—C5'—H5'	119.4	C26—C21—N1	119.68 (14)
C4—C5—C6	121.11 (16)	C23'—C22'—C21'	119.87 (16)
C4—C5—H5	119.4	C23'—C22'—H22'	120.1
C6—C5—H5	119.4	C21'—C22'—H22'	120.1
C5—C6—C1	118.83 (15)	C21—C22—C23	119.96 (16)
C5—C6—C7	121.35 (14)	C21—C22—H22	120.0
C1—C6—C7	119.62 (13)	C23—C22—H22	120.0
C5'—C6'—C1'	119.00 (15)	C24'—C23'—C22'	120.44 (18)
C5'—C6'—C7'	121.50 (14)	C24'—C23'—H23'	119.8
C1'—C6'—C7'	119.35 (14)	C22'—C23'—H23'	119.8
O1'—C7'—C8'	119.40 (15)	C24—C23—C22	120.77 (17)
O1'—C7'—C6'	119.77 (14)	C24—C23—H23	119.6
C8'—C7'—C6'	120.83 (13)	C22—C23—H23	119.6
O1—C7—C8	119.93 (15)	C25—C24—C23	119.42 (16)
O1—C7—C6	119.49 (15)	C25—C24—H24	120.3
C8—C7—C6	120.57 (13)	C23—C24—H24	120.3
C13'—C8'—C9'	118.59 (15)	C25'—C24'—C23'	119.82 (17)
C13'—C8'—C7'	118.81 (15)	C25'—C24'—H24'	120.1
C9'—C8'—C7'	122.48 (14)	C23'—C24'—H24'	120.1
C13—C8—C9	118.70 (15)	C24—C25—C26	120.42 (17)
C13—C8—C7	118.46 (14)	C24—C25—H25	119.8
C9—C8—C7	122.71 (14)	C26—C25—H25	119.8
C10—C9—C8	120.16 (16)	C24'—C25'—C26'	120.28 (17)
C10—C9—H9	119.9	C24'—C25'—H25'	119.9
C8—C9—H9	119.9	C26'—C25'—H25'	119.9
C10'—C9'—C8'	120.29 (16)	C25—C26—C21	120.70 (17)
C10'—C9'—H9'	119.9	C25—C26—H26	119.7
C8'—C9'—H9'	119.9	C21—C26—H26	119.7
C11'—C10'—C9'	120.51 (18)	C21'—C26'—C25'	120.13 (17)
C11'—C10'—H10'	119.7	C21'—C26'—H26'	119.9
C9'—C10'—H10'	119.7	C25'—C26'—H26'	119.9
C11—C10—C9	120.47 (17)	C28—C27—C32	119.96 (15)
C11—C10—H10	119.8	C28—C27—N1	120.04 (14)
C9—C10—H10	119.8	C32—C27—N1	119.99 (15)
C10'—C11'—C12'	119.88 (18)	C28'—C27'—C32'	119.61 (14)
C10'—C11'—H11'	120.1	C28'—C27'—N1'	119.81 (14)
C12'—C11'—H11'	120.1	C32'—C27'—N1'	120.58 (14)
C10—C11—C12	119.91 (18)	C27—C28—C29	120.11 (17)
C10—C11—H11	120.0	C27—C28—H28	119.9
C12—C11—H11	120.0	C29—C28—H28	119.9
C11'—C12'—C13'	120.29 (18)	C27'—C28'—C29'	120.05 (16)
C11'—C12'—H12'	119.9	C27'—C28'—H28'	120.0
C13'—C12'—H12'	119.9	C29'—C28'—H28'	120.0
C11—C12—C13	119.84 (18)	C30'—C29'—C28'	120.11 (17)
C11—C12—H12	120.1	C30'—C29'—H29'	119.9
C13—C12—H12	120.1	C28'—C29'—H29'	119.9
C12'—C13'—C8'	120.40 (18)	C30—C29—C28	119.70 (19)
C12'—C13'—H13'	119.8	C30—C29—H29	120.2
C8'—C13'—H13'	119.8	C28—C29—H29	120.2
C12—C13—C8	120.87 (17)	C31'—C30'—C29'	120.12 (16)
C12—C13—H13	119.6	C31'—C30'—H30'	119.9
C8—C13—H13	119.6	C29'—C30'—H30'	119.9
O2'—C14'—C15'	121.90 (15)	C31—C30—C29	120.41 (17)
O2'—C14'—C1'	119.04 (14)	C31—C30—H30	119.8
C15'—C14'—C1'	118.97 (13)	C29—C30—H30	119.8
O2—C14—C15	122.18 (14)	C30—C31—C32	120.09 (18)
O2—C14—C1	119.49 (14)	C30—C31—H31	120.0
C15—C14—C1	118.14 (13)	C32—C31—H31	120.0
C20—C15—C16	117.78 (13)	C30'—C31'—C32'	119.96 (17)
C20—C15—C14	122.31 (13)	C30'—C31'—H31'	120.0
C16—C15—C14	119.90 (13)	C32'—C31'—H31'	120.0
C16'—C15'—C20'	117.38 (13)	C31—C32—C27	119.72 (18)
C16'—C15'—C14'	120.11 (13)	C31—C32—H32	120.1
C20'—C15'—C14'	122.42 (13)	C27—C32—H32	120.1
C17—C16—C15	121.14 (14)	C27'—C32'—C31'	120.14 (16)
C17—C16—H16	119.4	C27'—C32'—H32'	119.9
C15—C16—H16	119.4	C31'—C32'—H32'	119.9
C17'—C16'—C15'	121.93 (14)	C18'—N1'—C21'	120.84 (12)
C17'—C16'—H16'	119.0	C18'—N1'—C27'	121.29 (12)
C15'—C16'—H16'	119.0	C21'—N1'—C27'	117.73 (12)
C16'—C17'—C18'	120.58 (14)	C18—N1—C21	121.97 (12)
C16'—C17'—H17'	119.7	C18—N1—C27	119.64 (12)
C18'—C17'—H17'	119.7	C21—N1—C27	117.71 (12)
C6—C1—C2—C3	−0.3 (2)	C14'—C15'—C16'—C17'	−175.11 (15)
C14—C1—C2—C3	176.08 (15)	C15'—C16'—C17'—C18'	1.0 (2)
C6'—C1'—C2'—C3'	0.0 (2)	C15—C16—C17—C18	2.2 (2)
C14'—C1'—C2'—C3'	175.97 (15)	C16'—C17'—C18'—C19'	−3.0 (2)
C1—C2—C3—C4	0.7 (3)	C16'—C17'—C18'—N1'	177.22 (14)
C1'—C2'—C3'—C4'	0.9 (3)	C16—C17—C18—C19	−4.6 (2)
C2'—C3'—C4'—C5'	−0.7 (3)	C16—C17—C18—N1	175.87 (15)
C2—C3—C4—C5	−0.5 (3)	C17—C18—C19—C20	2.9 (2)
C3'—C4'—C5'—C6'	−0.5 (3)	N1—C18—C19—C20	−177.47 (15)
C3—C4—C5—C6	−0.2 (3)	N1'—C18'—C19'—C20'	−177.88 (14)
C4—C5—C6—C1	0.6 (2)	C17'—C18'—C19'—C20'	2.4 (2)
C4—C5—C6—C7	175.47 (14)	C18'—C19'—C20'—C15'	0.3 (2)
C2—C1—C6—C5	−0.4 (2)	C16'—C15'—C20'—C19'	−2.3 (2)
C14—C1—C6—C5	−176.49 (14)	C14'—C15'—C20'—C19'	174.37 (15)
C2—C1—C6—C7	−175.34 (14)	C18—C19—C20—C15	1.0 (2)
C14—C1—C6—C7	8.6 (2)	C16—C15—C20—C19	−3.4 (2)
C4'—C5'—C6'—C1'	1.5 (2)	C14—C15—C20—C19	175.40 (15)
C4'—C5'—C6'—C7'	176.82 (14)	C26'—C21'—C22'—C23'	−1.8 (2)
C2'—C1'—C6'—C5'	−1.2 (2)	N1'—C21'—C22'—C23'	178.33 (15)
C14'—C1'—C6'—C5'	−176.92 (13)	C26—C21—C22—C23	−2.2 (3)
C2'—C1'—C6'—C7'	−176.66 (14)	N1—C21—C22—C23	179.60 (15)
C14'—C1'—C6'—C7'	7.6 (2)	C21'—C22'—C23'—C24'	0.9 (3)
C5'—C6'—C7'—O1'	−147.81 (16)	C21—C22—C23—C24	1.5 (3)
C1'—C6'—C7'—O1'	27.5 (2)	C22—C23—C24—C25	0.3 (3)
C5'—C6'—C7'—C8'	32.1 (2)	C22'—C23'—C24'—C25'	0.8 (3)
C1'—C6'—C7'—C8'	−152.57 (14)	C23—C24—C25—C26	−1.4 (3)
C5—C6—C7—O1	−147.02 (16)	C23'—C24'—C25'—C26'	−1.6 (3)
C1—C6—C7—O1	27.8 (2)	C24—C25—C26—C21	0.7 (3)
C5—C6—C7—C8	32.0 (2)	C22—C21—C26—C25	1.1 (3)
C1—C6—C7—C8	−153.19 (14)	N1—C21—C26—C25	179.38 (16)
O1'—C7'—C8'—C13'	28.5 (2)	C22'—C21'—C26'—C25'	1.0 (2)
C6'—C7'—C8'—C13'	−151.40 (15)	N1'—C21'—C26'—C25'	−179.12 (15)
O1'—C7'—C8'—C9'	−147.49 (17)	C24'—C25'—C26'—C21'	0.7 (3)
C6'—C7'—C8'—C9'	32.6 (2)	C32—C27—C28—C29	0.7 (2)
O1—C7—C8—C13	27.9 (2)	N1—C27—C28—C29	−177.86 (14)
C6—C7—C8—C13	−151.13 (15)	C32'—C27'—C28'—C29'	0.2 (2)
O1—C7—C8—C9	−147.83 (16)	N1'—C27'—C28'—C29'	−179.71 (14)
C6—C7—C8—C9	33.2 (2)	C27'—C28'—C29'—C30'	0.7 (2)
C13—C8—C9—C10	−1.3 (2)	C27—C28—C29—C30	0.0 (3)
C7—C8—C9—C10	174.38 (15)	C28'—C29'—C30'—C31'	−0.7 (3)
C13'—C8'—C9'—C10'	−1.4 (2)	C28—C29—C30—C31	−0.6 (3)
C7'—C8'—C9'—C10'	174.54 (15)	C29—C30—C31—C32	0.5 (3)
C8'—C9'—C10'—C11'	1.7 (3)	C29'—C30'—C31'—C32'	−0.2 (3)
C8—C9—C10—C11	1.5 (3)	C30—C31—C32—C27	0.3 (3)
C9'—C10'—C11'—C12'	−0.4 (3)	C28—C27—C32—C31	−0.8 (2)
C9—C10—C11—C12	0.1 (3)	N1—C27—C32—C31	177.71 (15)
C10'—C11'—C12'—C13'	−1.3 (3)	C28'—C27'—C32'—C31'	−1.2 (2)
C10—C11—C12—C13	−1.8 (3)	N1'—C27'—C32'—C31'	178.76 (14)
C11'—C12'—C13'—C8'	1.6 (3)	C30'—C31'—C32'—C27'	1.2 (3)
C9'—C8'—C13'—C12'	−0.2 (2)	C19'—C18'—N1'—C21'	163.18 (14)
C7'—C8'—C13'—C12'	−176.34 (16)	C17'—C18'—N1'—C21'	−17.1 (2)
C11—C12—C13—C8	1.9 (3)	C19'—C18'—N1'—C27'	−12.4 (2)
C9—C8—C13—C12	−0.4 (2)	C17'—C18'—N1'—C27'	167.36 (14)
C7—C8—C13—C12	−176.27 (16)	C26'—C21'—N1'—C18'	127.57 (16)
C2'—C1'—C14'—O2'	−98.22 (19)	C22'—C21'—N1'—C18'	−52.5 (2)
C6'—C1'—C14'—O2'	77.5 (2)	C26'—C21'—N1'—C27'	−56.7 (2)
C2'—C1'—C14'—C15'	78.33 (19)	C22'—C21'—N1'—C27'	123.21 (16)
C6'—C1'—C14'—C15'	−105.90 (17)	C28'—C27'—N1'—C18'	122.05 (16)
C2—C1—C14—O2	−106.64 (18)	C32'—C27'—N1'—C18'	−57.9 (2)
C6—C1—C14—O2	69.5 (2)	C28'—C27'—N1'—C21'	−53.67 (19)
C2—C1—C14—C15	68.51 (19)	C32'—C27'—N1'—C21'	126.39 (16)
C6—C1—C14—C15	−115.31 (16)	C19—C18—N1—C21	156.14 (15)
O2—C14—C15—C20	−165.65 (16)	C17—C18—N1—C21	−24.3 (2)
C1—C14—C15—C20	19.3 (2)	C19—C18—N1—C27	−14.2 (2)
O2—C14—C15—C16	13.1 (2)	C17—C18—N1—C27	165.40 (15)
C1—C14—C15—C16	−161.93 (14)	C22—C21—N1—C18	−41.1 (2)
O2'—C14'—C15'—C16'	9.0 (2)	C26—C21—N1—C18	140.76 (16)
C1'—C14'—C15'—C16'	−167.45 (14)	C22—C21—N1—C27	129.43 (17)
O2'—C14'—C15'—C20'	−167.53 (16)	C26—C21—N1—C27	−48.8 (2)
C1'—C14'—C15'—C20'	16.0 (2)	C28—C27—N1—C18	110.22 (17)
C20—C15—C16—C17	1.7 (2)	C32—C27—N1—C18	−68.3 (2)
C14—C15—C16—C17	−177.04 (14)	C28—C27—N1—C21	−60.5 (2)
C20'—C15'—C16'—C17'	1.6 (2)	C32—C27—N1—C21	120.97 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C31′—H31′···O2i	0.93	2.51	3.419 (2)	166
C16—H16···O2′	0.93	2.44	3.219 (2)	141
C30′—H30′···Cg1i	0.93	3.00	3.894 (2)	162
C4′—H4′···Cg2ii	0.93	2.95	3.731 (2)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C8–C13 and C27′–C32′ phenyl rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C31′—H31′⋯O2i	0.93	2.51	3.419 (2)	166
C16—H16⋯O2′	0.93	2.44	3.219 (2)	141
C30′—H30′⋯Cg1i	0.93	3.00	3.894 (2)	162
C4′—H4′⋯Cg2ii	0.93	2.95	3.731 (2)	142

Symmetry codes: (i) ; (ii) .