4,4',6,6'-Tetra-tert-butyl-2,2'-[1,2-phenyl-enebis(nitrilo-methyl-idyne)]diphenol acetone solvate.

In the Schiff base mol-ecule of the title compound, C(36)H(48)N(2)O(2)·C(3)H(6)O, the central benzene ring makes dihedral angles of 46.64 (10) and 49.34 (10)° with the two outer benzene rings, and the two outer benzene rings form an angle of 39.13 (8)°. There are two intra-molecular O-H⋯N hydrogen bonds involving the two hydr-oxy groups, which generate S(6) ring motifs. In the crystal structure, the Schiff base mol-ecules are linked into a chain along the a axis by C-H⋯π inter-actions. The acetone solvent mol-ecules are attached to the chain via C-H⋯O hydrogen bonds.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For ring-motifs, see: Bernstein et al. (1995 ▶). For biological activities of Schiff base compounds, see: Dao et al. (2000 ▶); Eltayeb & Ahmed (2005a ▶,b ▶); Karthikeyan et al. (2006 ▶); Sriram et al. (2006 ▶). For related structures, see: Eltayeb, Teoh, Chantrapromma et al. (2007 ▶); Eltayeb, Teoh, Teh et al. (2007a ▶,b ▶).

Experimental

Crystal data

C36H48N2O2·C3H6O

M = 598.84

Triclinic,

a = 10.0008 (2) Å

b = 12.0020 (3) Å

c = 17.0366 (4) Å

α = 82.068 (1)°

β = 86.320 (1)°

γ = 65.764 (1)°

V = 1846.76 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 296 (2) K

0.59 × 0.55 × 0.43 mm

Data collection

Bruker SMART APEX2 CCD area-detecto diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.962, T max = 0.972

26090 measured reflections

8384 independent reflections

5874 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.183

S = 1.04

8384 reflections

419 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808003905/ci2559sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808003905/ci2559Isup2.hkl

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

C36H48N2O2·C3H6O	Z = 2
Mr = 598.84	F000 = 652
Triclinic, P1	Dx = 1.077 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 10.0008 (2) Å	Cell parameters from 8384 reflections
b = 12.0020 (3) Å	θ = 1.9–27.5º
c = 17.0366 (4) Å	µ = 0.07 mm−1
α = 82.068 (1)º	T = 296 (2) K
β = 86.320 (1)º	Block, orange
γ = 65.764 (1)º	0.59 × 0.55 × 0.43 mm
V = 1846.76 (7) Å3

Bruker SMART APEX2 CCD area-detecto diffractometer	8384 independent reflections
Radiation source: fine-focus sealed tube	5874 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.022
Detector resolution: 8.33 pixels mm-1	θmax = 27.5º
T = 296(2) K	θmin = 1.9º
ω scans	h = −11→12
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −15→15
Tmin = 0.962, Tmax = 0.972	l = −22→22
26090 measured 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)] = 0.060	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.183	w = 1/[σ2(Fo2) + (0.085P)2 + 0.5109P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
8384 reflections	Δρmax = 0.45 e Å−3
419 parameters	Δρmin = −0.28 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
O1	0.24853 (14)	0.02581 (13)	0.23910 (8)	0.0551 (3)
O2	−0.02994 (14)	0.37492 (14)	0.24879 (8)	0.0560 (4)
N1	0.25681 (16)	0.14200 (13)	0.10087 (8)	0.0460 (3)
N2	−0.01847 (16)	0.32660 (14)	0.10401 (8)	0.0459 (3)
C1	0.38900 (17)	0.00930 (15)	0.24923 (10)	0.0407 (4)
C2	0.45915 (18)	−0.04982 (14)	0.32187 (10)	0.0413 (4)
C3	0.60129 (18)	−0.06050 (15)	0.32878 (10)	0.0449 (4)
H3A	0.6489	−0.0987	0.3765	0.054*
C4	0.67862 (18)	−0.01843 (15)	0.26978 (11)	0.0451 (4)
C5	0.60684 (19)	0.03771 (16)	0.19953 (11)	0.0460 (4)
H5A	0.6550	0.0666	0.1586	0.055*
C6	0.46270 (18)	0.05235 (15)	0.18822 (10)	0.0421 (4)
C7	0.3908 (2)	0.11843 (16)	0.11444 (10)	0.0449 (4)
H7A	0.4441	0.1448	0.0753	0.054*
C8	0.19331 (19)	0.21018 (16)	0.02816 (9)	0.0447 (4)
C9	0.2644 (2)	0.1850 (2)	−0.04413 (11)	0.0614 (5)
H9A	0.3569	0.1211	−0.0455	0.074*
C10	0.1993 (3)	0.2537 (2)	−0.11419 (11)	0.0704 (6)
H10A	0.2480	0.2363	−0.1623	0.084*
C11	0.0627 (3)	0.3476 (2)	−0.11230 (11)	0.0668 (6)
H11A	0.0196	0.3952	−0.1592	0.080*
C12	−0.0113 (2)	0.37196 (19)	−0.04127 (11)	0.0575 (5)
H12A	−0.1044	0.4354	−0.0406	0.069*
C13	0.05201 (19)	0.30244 (16)	0.02944 (9)	0.0438 (4)
C14	−0.1540 (2)	0.34565 (17)	0.11173 (10)	0.0489 (4)
H14A	−0.2026	0.3410	0.0683	0.059*
C15	−0.23510 (19)	0.37409 (16)	0.18511 (10)	0.0449 (4)
C16	−0.38016 (19)	0.38473 (17)	0.18917 (11)	0.0489 (4)
H16A	−0.4213	0.3742	0.1448	0.059*
C17	−0.46321 (18)	0.41034 (15)	0.25708 (11)	0.0445 (4)
C18	−0.39582 (18)	0.42637 (15)	0.32176 (10)	0.0439 (4)
H18A	−0.4512	0.4449	0.3679	0.053*
C19	−0.25311 (18)	0.41677 (15)	0.32213 (10)	0.0417 (4)
C20	−0.17137 (18)	0.38860 (16)	0.25182 (10)	0.0424 (4)
C21	0.8335 (2)	−0.03120 (18)	0.28575 (13)	0.0549 (5)
C22	0.9056 (3)	0.0030 (4)	0.20973 (19)	0.1070 (11)
H22A	0.9107	−0.0499	0.1711	0.160*
H22B	1.0028	−0.0068	0.2212	0.160*
H22C	0.8485	0.0870	0.1892	0.160*
C23	0.9286 (3)	−0.1632 (3)	0.3171 (3)	0.1184 (13)
H23A	0.8956	−0.1825	0.3693	0.178*
H23B	1.0287	−0.1732	0.3194	0.178*
H23C	0.9218	−0.2174	0.2826	0.178*
C24	0.8236 (3)	0.0569 (3)	0.3431 (2)	0.0993 (10)
H24A	0.7817	0.0362	0.3923	0.149*
H24B	0.7628	0.1394	0.3212	0.149*
H24C	0.9199	0.0513	0.3524	0.149*
C25	−0.62039 (19)	0.41811 (17)	0.26502 (12)	0.0504 (4)
C26	−0.6241 (3)	0.3137 (2)	0.32638 (16)	0.0759 (7)
H26A	−0.5579	0.2361	0.3104	0.114*
H26B	−0.7218	0.3169	0.3304	0.114*
H26C	−0.5950	0.3226	0.3770	0.114*
C27	−0.6760 (2)	0.4069 (2)	0.18631 (15)	0.0714 (6)
H27A	−0.6773	0.4737	0.1477	0.107*
H27B	−0.7733	0.4100	0.1935	0.107*
H27C	−0.6122	0.3301	0.1683	0.107*
C28	−0.7245 (2)	0.5417 (2)	0.29181 (15)	0.0668 (6)
H28A	−0.7242	0.6076	0.2529	0.100*
H28B	−0.6925	0.5502	0.3417	0.100*
H28C	−0.8220	0.5447	0.2975	0.100*
C29	−0.1868 (2)	0.43580 (17)	0.39531 (10)	0.0487 (4)
C30	−0.1413 (3)	0.5437 (2)	0.37445 (14)	0.0736 (6)
H30A	−0.2253	0.6167	0.3564	0.110*
H30B	−0.0679	0.5251	0.3333	0.110*
H30C	−0.1022	0.5571	0.4206	0.110*
C31	−0.0546 (3)	0.3177 (2)	0.42414 (13)	0.0756 (7)
H31A	0.0179	0.2971	0.3827	0.113*
H31B	−0.0856	0.2516	0.4381	0.113*
H31C	−0.0133	0.3304	0.4697	0.113*
C32	−0.2966 (2)	0.4672 (2)	0.46406 (11)	0.0639 (5)
H32A	−0.3809	0.5410	0.4477	0.096*
H32B	−0.2516	0.4797	0.5082	0.096*
H32C	−0.3263	0.4007	0.4794	0.096*
C33	0.3806 (2)	−0.09823 (17)	0.38899 (10)	0.0485 (4)
C34	0.2432 (2)	0.0077 (2)	0.41472 (13)	0.0718 (6)
H34A	0.2702	0.0686	0.4316	0.108*
H34B	0.1960	−0.0233	0.4578	0.108*
H34C	0.1770	0.0441	0.3709	0.108*
C35	0.3409 (3)	−0.1970 (2)	0.36056 (14)	0.0717 (6)
H35A	0.2795	−0.1620	0.3148	0.108*
H35B	0.2896	−0.2264	0.4021	0.108*
H35C	0.4290	−0.2643	0.3470	0.108*
C36	0.4771 (2)	−0.15914 (19)	0.46241 (11)	0.0597 (5)
H36A	0.5021	−0.0995	0.4828	0.090*
H36B	0.5651	−0.2258	0.4481	0.090*
H36C	0.4245	−0.1902	0.5023	0.090*
O3	0.6258 (5)	0.2364 (5)	0.0147 (2)	0.227 (2)
C37	0.8191 (10)	0.1323 (9)	−0.0542 (7)	0.345 (8)
H37A	0.8795	0.1561	−0.0245	0.517*
H37B	0.8476	0.1354	−0.1090	0.517*
H37C	0.8309	0.0501	−0.0342	0.517*
C38	0.6661 (8)	0.2165 (6)	−0.0462 (2)	0.176 (3)
C39	0.5935 (11)	0.2473 (7)	−0.1217 (3)	0.266 (5)
H39A	0.5220	0.3310	−0.1262	0.399*
H39B	0.5456	0.1933	−0.1254	0.399*
H39C	0.6646	0.2381	−0.1637	0.399*
H1O1	0.221 (3)	0.072 (2)	0.1925 (15)	0.083 (8)*
H1O2	0.001 (3)	0.353 (2)	0.2023 (16)	0.084 (8)*

	U11	U22	U33	U12	U13	U23
O1	0.0384 (7)	0.0755 (9)	0.0528 (7)	−0.0286 (6)	−0.0115 (6)	0.0104 (6)
O2	0.0366 (7)	0.0876 (10)	0.0494 (7)	−0.0283 (7)	0.0041 (6)	−0.0191 (7)
N1	0.0396 (8)	0.0530 (8)	0.0396 (7)	−0.0134 (7)	−0.0015 (6)	−0.0038 (6)
N2	0.0390 (8)	0.0555 (8)	0.0398 (7)	−0.0151 (7)	0.0017 (6)	−0.0090 (6)
C1	0.0317 (8)	0.0428 (8)	0.0479 (9)	−0.0149 (7)	−0.0043 (7)	−0.0050 (7)
C2	0.0369 (9)	0.0401 (8)	0.0471 (9)	−0.0157 (7)	−0.0050 (7)	−0.0041 (7)
C3	0.0379 (9)	0.0432 (9)	0.0523 (9)	−0.0144 (7)	−0.0097 (8)	−0.0040 (7)
C4	0.0312 (8)	0.0437 (9)	0.0605 (10)	−0.0134 (7)	−0.0016 (8)	−0.0124 (7)
C5	0.0356 (9)	0.0499 (9)	0.0530 (10)	−0.0180 (8)	0.0053 (7)	−0.0088 (7)
C6	0.0359 (9)	0.0441 (8)	0.0444 (8)	−0.0136 (7)	−0.0004 (7)	−0.0073 (7)
C7	0.0420 (9)	0.0495 (9)	0.0412 (8)	−0.0169 (8)	0.0051 (7)	−0.0068 (7)
C8	0.0452 (10)	0.0494 (9)	0.0367 (8)	−0.0163 (8)	−0.0004 (7)	−0.0055 (7)
C9	0.0559 (12)	0.0681 (12)	0.0441 (10)	−0.0087 (10)	0.0054 (9)	−0.0112 (9)
C10	0.0746 (15)	0.0860 (15)	0.0364 (9)	−0.0185 (13)	0.0076 (9)	−0.0103 (9)
C11	0.0787 (15)	0.0719 (13)	0.0367 (9)	−0.0194 (12)	−0.0073 (9)	0.0030 (8)
C12	0.0537 (11)	0.0595 (11)	0.0466 (10)	−0.0104 (9)	−0.0061 (9)	−0.0029 (8)
C13	0.0446 (10)	0.0488 (9)	0.0372 (8)	−0.0175 (8)	−0.0008 (7)	−0.0074 (7)
C14	0.0427 (10)	0.0597 (10)	0.0431 (9)	−0.0176 (9)	−0.0041 (8)	−0.0109 (8)
C15	0.0356 (9)	0.0530 (9)	0.0445 (9)	−0.0155 (8)	0.0001 (7)	−0.0089 (7)
C16	0.0385 (9)	0.0598 (10)	0.0487 (9)	−0.0181 (8)	−0.0047 (8)	−0.0119 (8)
C17	0.0327 (9)	0.0433 (8)	0.0558 (10)	−0.0133 (7)	−0.0003 (7)	−0.0076 (7)
C18	0.0375 (9)	0.0458 (9)	0.0466 (9)	−0.0151 (7)	0.0046 (7)	−0.0079 (7)
C19	0.0392 (9)	0.0434 (8)	0.0429 (8)	−0.0171 (7)	0.0012 (7)	−0.0063 (7)
C20	0.0336 (8)	0.0486 (9)	0.0458 (9)	−0.0170 (7)	−0.0008 (7)	−0.0068 (7)
C21	0.0337 (9)	0.0586 (11)	0.0756 (13)	−0.0206 (8)	−0.0056 (9)	−0.0100 (9)
C22	0.0550 (15)	0.169 (3)	0.113 (2)	−0.0639 (19)	0.0065 (15)	−0.014 (2)
C23	0.0403 (13)	0.0770 (17)	0.225 (4)	−0.0162 (12)	−0.0399 (18)	0.016 (2)
C24	0.0628 (16)	0.123 (2)	0.133 (2)	−0.0449 (16)	−0.0094 (16)	−0.056 (2)
C25	0.0330 (9)	0.0524 (10)	0.0653 (11)	−0.0167 (8)	−0.0002 (8)	−0.0076 (8)
C26	0.0548 (13)	0.0703 (14)	0.1036 (18)	−0.0326 (11)	−0.0001 (12)	0.0087 (13)
C27	0.0423 (11)	0.0876 (16)	0.0907 (16)	−0.0283 (11)	−0.0076 (11)	−0.0222 (13)
C28	0.0402 (11)	0.0654 (12)	0.0904 (15)	−0.0158 (10)	0.0093 (10)	−0.0183 (11)
C29	0.0464 (10)	0.0596 (10)	0.0438 (9)	−0.0237 (9)	0.0002 (8)	−0.0122 (8)
C30	0.0842 (17)	0.0917 (16)	0.0721 (14)	−0.0584 (14)	0.0134 (12)	−0.0312 (12)
C31	0.0637 (14)	0.0875 (16)	0.0606 (12)	−0.0127 (12)	−0.0173 (11)	−0.0103 (11)
C32	0.0688 (14)	0.0813 (14)	0.0479 (10)	−0.0347 (12)	0.0078 (10)	−0.0191 (10)
C33	0.0442 (10)	0.0535 (10)	0.0484 (9)	−0.0227 (8)	−0.0074 (8)	0.0037 (7)
C34	0.0514 (12)	0.0857 (15)	0.0601 (12)	−0.0141 (11)	0.0040 (10)	0.0031 (11)
C35	0.0855 (16)	0.0786 (14)	0.0700 (13)	−0.0571 (13)	−0.0198 (12)	0.0145 (11)
C36	0.0620 (13)	0.0645 (12)	0.0500 (10)	−0.0255 (10)	−0.0116 (9)	0.0062 (9)
O3	0.243 (4)	0.409 (7)	0.144 (3)	−0.231 (5)	0.094 (3)	−0.137 (3)
C37	0.305 (11)	0.372 (13)	0.507 (18)	−0.242 (10)	0.246 (12)	−0.320 (13)
C38	0.300 (7)	0.273 (6)	0.091 (3)	−0.247 (6)	0.087 (4)	−0.083 (3)
C39	0.493 (15)	0.306 (9)	0.124 (4)	−0.295 (11)	0.035 (6)	−0.019 (5)

O1—C1	1.3548 (19)	C23—H23C	0.96
O1—H1O1	0.89 (3)	C24—H24A	0.96
O2—C20	1.354 (2)	C24—H24B	0.96
O2—H1O2	0.87 (3)	C24—H24C	0.96
N1—C7	1.280 (2)	C25—C27	1.527 (3)
N1—C8	1.415 (2)	C25—C26	1.528 (3)
N2—C14	1.280 (2)	C25—C28	1.533 (3)
N2—C13	1.419 (2)	C26—H26A	0.96
C1—C6	1.399 (2)	C26—H26B	0.96
C1—C2	1.410 (2)	C26—H26C	0.96
C2—C3	1.385 (2)	C27—H27A	0.96
C2—C33	1.529 (2)	C27—H27B	0.96
C3—C4	1.394 (3)	C27—H27C	0.96
C3—H3A	0.93	C28—H28A	0.96
C4—C5	1.376 (2)	C28—H28B	0.96
C4—C21	1.531 (2)	C28—H28C	0.96
C5—C6	1.402 (2)	C29—C32	1.529 (3)
C5—H5A	0.93	C29—C30	1.532 (3)
C6—C7	1.449 (2)	C29—C31	1.533 (3)
C7—H7A	0.93	C30—H30A	0.96
C8—C9	1.388 (2)	C30—H30B	0.96
C8—C13	1.393 (2)	C30—H30C	0.96
C9—C10	1.384 (3)	C31—H31A	0.96
C9—H9A	0.93	C31—H31B	0.96
C10—C11	1.371 (3)	C31—H31C	0.96
C10—H10A	0.93	C32—H32A	0.96
C11—C12	1.379 (3)	C32—H32B	0.96
C11—H11A	0.93	C32—H32C	0.96
C12—C13	1.391 (2)	C33—C34	1.529 (3)
C12—H12A	0.93	C33—C36	1.534 (2)
C14—C15	1.448 (2)	C33—C35	1.538 (3)
C14—H14A	0.93	C34—H34A	0.96
C15—C16	1.401 (2)	C34—H34B	0.96
C15—C20	1.402 (2)	C34—H34C	0.96
C16—C17	1.374 (2)	C35—H35A	0.96
C16—H16A	0.93	C35—H35B	0.96
C17—C18	1.402 (2)	C35—H35C	0.96
C17—C25	1.534 (2)	C36—H36A	0.96
C18—C19	1.384 (2)	C36—H36B	0.96
C18—H18A	0.93	C36—H36C	0.96
C19—C20	1.406 (2)	O3—C38	1.111 (4)
C19—C29	1.535 (2)	C37—C38	1.456 (10)
C21—C24	1.507 (3)	C37—H37A	0.96
C21—C23	1.515 (3)	C37—H37B	0.96
C21—C22	1.530 (4)	C37—H37C	0.96
C22—H22A	0.96	C38—C39	1.444 (8)
C22—H22B	0.96	C39—H39A	0.96
C22—H22C	0.96	C39—H39B	0.96
C23—H23A	0.96	C39—H39C	0.96
C23—H23B	0.96
C1—O1—H1O1	105.8 (16)	C27—C25—C26	108.66 (19)
C20—O2—H1O2	104.6 (17)	C27—C25—C28	107.99 (17)
C7—N1—C8	119.31 (15)	C26—C25—C28	109.09 (18)
C14—N2—C13	119.35 (15)	C27—C25—C17	111.42 (16)
O1—C1—C6	119.97 (14)	C26—C25—C17	109.29 (15)
O1—C1—C2	119.56 (15)	C28—C25—C17	110.34 (16)
C6—C1—C2	120.47 (15)	C25—C26—H26A	109.5
C3—C2—C1	116.38 (15)	C25—C26—H26B	109.5
C3—C2—C33	122.46 (14)	H26A—C26—H26B	109.5
C1—C2—C33	121.16 (15)	C25—C26—H26C	109.5
C2—C3—C4	125.10 (15)	H26A—C26—H26C	109.5
C2—C3—H3A	117.5	H26B—C26—H26C	109.5
C4—C3—H3A	117.5	C25—C27—H27A	109.5
C5—C4—C3	116.75 (16)	C25—C27—H27B	109.5
C5—C4—C21	123.03 (17)	H27A—C27—H27B	109.5
C3—C4—C21	120.18 (16)	C25—C27—H27C	109.5
C4—C5—C6	121.45 (17)	H27A—C27—H27C	109.5
C4—C5—H5A	119.3	H27B—C27—H27C	109.5
C6—C5—H5A	119.3	C25—C28—H28A	109.5
C1—C6—C5	119.85 (15)	C25—C28—H28B	109.5
C1—C6—C7	121.48 (15)	H28A—C28—H28B	109.5
C5—C6—C7	118.57 (16)	C25—C28—H28C	109.5
N1—C7—C6	122.76 (16)	H28A—C28—H28C	109.5
N1—C7—H7A	118.6	H28B—C28—H28C	109.5
C6—C7—H7A	118.6	C32—C29—C30	107.16 (16)
C9—C8—C13	119.21 (16)	C32—C29—C31	107.54 (16)
C9—C8—N1	122.34 (16)	C30—C29—C31	110.67 (19)
C13—C8—N1	118.40 (14)	C32—C29—C19	112.08 (16)
C10—C9—C8	120.87 (18)	C30—C29—C19	109.44 (16)
C10—C9—H9A	119.6	C31—C29—C19	109.92 (16)
C8—C9—H9A	119.6	C29—C30—H30A	109.5
C11—C10—C9	119.65 (18)	C29—C30—H30B	109.5
C11—C10—H10A	120.2	H30A—C30—H30B	109.5
C9—C10—H10A	120.2	C29—C30—H30C	109.5
C10—C11—C12	120.33 (18)	H30A—C30—H30C	109.5
C10—C11—H11A	119.8	H30B—C30—H30C	109.5
C12—C11—H11A	119.8	C29—C31—H31A	109.5
C11—C12—C13	120.58 (18)	C29—C31—H31B	109.5
C11—C12—H12A	119.7	H31A—C31—H31B	109.5
C13—C12—H12A	119.7	C29—C31—H31C	109.5
C12—C13—C8	119.26 (16)	H31A—C31—H31C	109.5
C12—C13—N2	122.41 (16)	H31B—C31—H31C	109.5
C8—C13—N2	118.22 (14)	C29—C32—H32A	109.5
N2—C14—C15	122.85 (16)	C29—C32—H32B	109.5
N2—C14—H14A	118.6	H32A—C32—H32B	109.5
C15—C14—H14A	118.6	C29—C32—H32C	109.5
C16—C15—C20	119.76 (15)	H32A—C32—H32C	109.5
C16—C15—C14	118.42 (16)	H32B—C32—H32C	109.5
C20—C15—C14	121.81 (16)	C2—C33—C34	110.08 (15)
C17—C16—C15	121.63 (16)	C2—C33—C36	112.41 (15)
C17—C16—H16A	119.2	C34—C33—C36	107.34 (16)
C15—C16—H16A	119.2	C2—C33—C35	109.12 (16)
C16—C17—C18	116.59 (16)	C34—C33—C35	110.84 (18)
C16—C17—C25	123.30 (16)	C36—C33—C35	107.01 (16)
C18—C17—C25	120.08 (15)	C33—C34—H34A	109.5
C19—C18—C17	124.94 (16)	C33—C34—H34B	109.5
C19—C18—H18A	117.5	H34A—C34—H34B	109.5
C17—C18—H18A	117.5	C33—C34—H34C	109.5
C18—C19—C20	116.57 (15)	H34A—C34—H34C	109.5
C18—C19—C29	121.98 (15)	H34B—C34—H34C	109.5
C20—C19—C29	121.45 (15)	C33—C35—H35A	109.5
O2—C20—C15	119.90 (15)	C33—C35—H35B	109.5
O2—C20—C19	119.60 (15)	H35A—C35—H35B	109.5
C15—C20—C19	120.49 (16)	C33—C35—H35C	109.5
C24—C21—C23	111.8 (2)	H35A—C35—H35C	109.5
C24—C21—C22	107.3 (2)	H35B—C35—H35C	109.5
C23—C21—C22	107.7 (2)	C33—C36—H36A	109.5
C24—C21—C4	108.80 (17)	C33—C36—H36B	109.5
C23—C21—C4	110.02 (17)	H36A—C36—H36B	109.5
C22—C21—C4	111.11 (18)	C33—C36—H36C	109.5
C21—C22—H22A	109.5	H36A—C36—H36C	109.5
C21—C22—H22B	109.5	H36B—C36—H36C	109.5
H22A—C22—H22B	109.5	C38—C37—H37A	109.5
C21—C22—H22C	109.5	C38—C37—H37B	109.5
H22A—C22—H22C	109.5	H37A—C37—H37B	109.5
H22B—C22—H22C	109.5	C38—C37—H37C	109.5
C21—C23—H23A	109.5	H37A—C37—H37C	109.5
C21—C23—H23B	109.5	H37B—C37—H37C	109.5
H23A—C23—H23B	109.5	O3—C38—C39	132.8 (9)
C21—C23—H23C	109.5	O3—C38—C37	116.6 (8)
H23A—C23—H23C	109.5	C39—C38—C37	110.2 (6)
H23B—C23—H23C	109.5	C38—C39—H39A	109.5
C21—C24—H24A	109.5	C38—C39—H39B	109.5
C21—C24—H24B	109.5	H39A—C39—H39B	109.5
H24A—C24—H24B	109.5	C38—C39—H39C	109.5
C21—C24—H24C	109.5	H39A—C39—H39C	109.5
H24A—C24—H24C	109.5	H39B—C39—H39C	109.5
H24B—C24—H24C	109.5
O1—C1—C2—C3	−178.29 (15)	C15—C16—C17—C18	0.6 (3)
C6—C1—C2—C3	0.8 (2)	C15—C16—C17—C25	−177.69 (16)
O1—C1—C2—C33	1.3 (2)	C16—C17—C18—C19	−0.9 (3)
C6—C1—C2—C33	−179.58 (15)	C25—C17—C18—C19	177.48 (15)
C1—C2—C3—C4	−0.5 (2)	C17—C18—C19—C20	−0.1 (3)
C33—C2—C3—C4	179.91 (16)	C17—C18—C19—C29	179.91 (16)
C2—C3—C4—C5	−0.1 (3)	C16—C15—C20—O2	178.13 (16)
C2—C3—C4—C21	177.60 (16)	C14—C15—C20—O2	−0.6 (3)
C3—C4—C5—C6	0.4 (2)	C16—C15—C20—C19	−1.6 (3)
C21—C4—C5—C6	−177.27 (16)	C14—C15—C20—C19	179.70 (16)
O1—C1—C6—C5	178.51 (15)	C18—C19—C20—O2	−178.41 (15)
C2—C1—C6—C5	−0.6 (2)	C29—C19—C20—O2	1.6 (2)
O1—C1—C6—C7	2.0 (2)	C18—C19—C20—C15	1.3 (2)
C2—C1—C6—C7	−177.09 (15)	C29—C19—C20—C15	−178.68 (16)
C4—C5—C6—C1	0.0 (3)	C5—C4—C21—C24	107.0 (2)
C4—C5—C6—C7	176.58 (16)	C3—C4—C21—C24	−70.5 (2)
C8—N1—C7—C6	178.16 (15)	C5—C4—C21—C23	−130.1 (2)
C1—C6—C7—N1	0.5 (3)	C3—C4—C21—C23	52.3 (3)
C5—C6—C7—N1	−176.03 (16)	C5—C4—C21—C22	−10.9 (3)
C7—N1—C8—C9	45.8 (3)	C3—C4—C21—C22	171.5 (2)
C7—N1—C8—C13	−136.81 (18)	C16—C17—C25—C27	−5.8 (2)
C13—C8—C9—C10	2.9 (3)	C18—C17—C25—C27	176.03 (17)
N1—C8—C9—C10	−179.8 (2)	C16—C17—C25—C26	114.3 (2)
C8—C9—C10—C11	−0.2 (4)	C18—C17—C25—C26	−63.9 (2)
C9—C10—C11—C12	−1.5 (4)	C16—C17—C25—C28	−125.7 (2)
C10—C11—C12—C13	0.6 (4)	C18—C17—C25—C28	56.1 (2)
C11—C12—C13—C8	2.0 (3)	C18—C19—C29—C32	−0.8 (2)
C11—C12—C13—N2	178.2 (2)	C20—C19—C29—C32	179.21 (16)
C9—C8—C13—C12	−3.7 (3)	C18—C19—C29—C30	−119.52 (19)
N1—C8—C13—C12	178.86 (17)	C20—C19—C29—C30	60.5 (2)
C9—C8—C13—N2	180.00 (18)	C18—C19—C29—C31	118.74 (19)
N1—C8—C13—N2	2.6 (3)	C20—C19—C29—C31	−61.3 (2)
C14—N2—C13—C12	45.9 (3)	C3—C2—C33—C34	119.17 (19)
C14—N2—C13—C8	−137.91 (18)	C1—C2—C33—C34	−60.4 (2)
C13—N2—C14—C15	−178.34 (16)	C3—C2—C33—C36	−0.4 (2)
N2—C14—C15—C16	−175.52 (17)	C1—C2—C33—C36	179.98 (16)
N2—C14—C15—C20	3.2 (3)	C3—C2—C33—C35	−118.98 (18)
C20—C15—C16—C17	0.6 (3)	C1—C2—C33—C35	61.4 (2)
C14—C15—C16—C17	179.36 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1	0.89 (2)	1.76 (3)	2.5809 (19)	153 (3)
O2—H1O2···N2	0.87 (3)	1.78 (3)	2.5956 (19)	155 (3)
C7—H7A···O3	0.93	2.58	3.460 (6)	158
C30—H30B···O2	0.96	2.36	2.994 (3)	123
C31—H31A···O2	0.96	2.34	2.989 (3)	124
C34—H34C···O1	0.96	2.32	2.968 (3)	124
C35—H35A···O1	0.96	2.35	2.996 (3)	124
C24—H24B···Cg2i	0.96	2.97	3.877 (3)	158
C26—H26A···Cg1ii	0.96	2.89	3.798 (2)	157

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the C1–C6 and C15–C20 ring centroids, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯N1	0.89 (2)	1.76 (3)	2.5809 (19)	153 (3)
O2—H1O2⋯N2	0.87 (3)	1.78 (3)	2.5956 (19)	155 (3)
C7—H7A⋯O3	0.93	2.58	3.460 (6)	158
C30—H30B⋯O2	0.96	2.36	2.994 (3)	123
C31—H31A⋯O2	0.96	2.34	2.989 (3)	124
C34—H34C⋯O1	0.96	2.32	2.968 (3)	124
C35—H35A⋯O1	0.96	2.35	2.996 (3)	124
C24—H24B⋯Cg2i	0.96	2.97	3.877 (3)	158
C26—H26A⋯Cg1ii	0.96	2.89	3.798 (2)	157

Symmetry codes: (i) ; (ii) .