4,5-Bis(2,4-di-tert-butyl-phen-oxy)phthalonitrile.

In the title compound, C(36)H(44)N(2)O(2), the dihedral angles between the phthalonitrile ring and the two di-tert-butyl-benzene rings are 68.134 (8) and 70.637 (11)°. The two nitrile groups are almost coplanar with the phthalonitrile ring except for one of the N atoms which deviates from the plane by 0.125 (4) Å. One of the tert-butyl groups is disordered over two orientations, with refined occupancies of 0.814 (6) and 0.186 (6). Intra-molecular C-H⋯O inter-actions stabilize the molecular structure. The crystal packing is stabilized by inter-molecular C-H⋯N inter-actions.

Related literature

For similar structures, see: Kartal et al. (2006 ▶); Petek et al. (2004 ▶); Dinçer et al. (2004 ▶). For other related structures, see: Şahin, et al. (2007 ▶); Wu et al. (2010 ▶); Yazıcı et al. (2004 ▶). For general background to phthalocyanines and metallophthalocyanines, see: Lenznoff & Lever (1989–1996 ▶); McKeown (1998 ▶); Wöhrle (2001 ▶).

Experimental

Crystal data

C36H44N2O2

M = 536.76

Triclinic,

a = 10.9468 (3) Å

b = 11.0416 (4) Å

c = 15.3133 (5) Å

α = 99.719 (1)°

β = 102.996 (1)°

γ = 110.963 (1)°

V = 1619.71 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 175 K

0.21 × 0.19 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.986, T max = 0.990

31007 measured reflections

7785 independent reflections

5255 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.148

S = 1.03

7785 reflections

399 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT-Plus (Bruker, 2008 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenberg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811006118/lr2003sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811006118/lr2003Isup2.hkl

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

C36H44N2O2	Z = 2
Mr = 536.76	F(000) = 580
Triclinic, P1	Dx = 1.1 Mg m−3
a = 10.9468 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.0416 (4) Å	Cell parameters from 7569 reflections
c = 15.3133 (5) Å	θ = 2.8–28.6°
α = 99.719 (1)°	µ = 0.07 mm−1
β = 102.996 (1)°	T = 175 K
γ = 110.963 (1)°	Cuboid, colourless
V = 1619.71 (9) Å3	0.21 × 0.19 × 0.14 mm

Bruker APEXII CCD diffractometer	5255 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 28°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −14→14
Tmin = 0.986, Tmax = 0.990	k = −14→14
31007 measured reflections	l = −20→20
7785 independent reflections

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0592P)2 + 0.5205P] where P = (Fo2 + 2Fc2)/3
7785 reflections	(Δ/σ)max = 0.017
399 parameters	Δρmax = 0.29 e Å−3
3 restraints	Δρmin = −0.30 e Å−3

Experimental. The intensity data was collected on a Bruker X8 ApexII 4 K Kappa CCD diffractometer using an exposure time of 40 s/frame. A total of 2019 frames were collected with a frame width of 0.5° covering up to θ = 28.57° with 99.4% completeness accomplished.

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 > 2σ(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	Occ. (<1)
C1	0.32485 (17)	−0.09576 (17)	0.99913 (12)	0.0399 (4)
C2	0.2111 (2)	0.0801 (2)	1.06591 (15)	0.0601 (6)
C3	0.27916 (16)	−0.02106 (15)	0.94090 (12)	0.0350 (3)
C4	0.22520 (18)	0.06741 (17)	0.97435 (12)	0.0399 (4)
C5	0.18274 (18)	0.14119 (17)	0.91845 (12)	0.0428 (4)
H5	0.1479	0.201	0.9412	0.051*
C6	0.19232 (16)	0.12561 (15)	0.82952 (11)	0.0344 (3)
C7	0.24483 (15)	0.03433 (15)	0.79532 (11)	0.0325 (3)
C8	0.28764 (16)	−0.03739 (15)	0.85123 (12)	0.0356 (4)
H8	0.3225	−0.0972	0.8286	0.043*
C11	0.32695 (16)	−0.03783 (15)	0.67397 (11)	0.0341 (3)
C12	0.46705 (18)	0.02362 (17)	0.71765 (12)	0.0422 (4)
H12	0.5042	0.099	0.7687	0.051*
C13	0.55247 (17)	−0.02689 (18)	0.68553 (12)	0.0421 (4)
H13	0.6467	0.0138	0.716	0.05*
C14	0.49885 (16)	−0.13740 (16)	0.60855 (11)	0.0342 (3)
C15	0.35667 (16)	−0.19584 (16)	0.56661 (11)	0.0335 (3)
H15	0.32	−0.2701	0.5148	0.04*
C16	0.26543 (16)	−0.15055 (15)	0.59701 (11)	0.0317 (3)
C17	0.10949 (16)	−0.22154 (16)	0.54796 (12)	0.0364 (4)
C18	0.07343 (19)	−0.33885 (19)	0.46378 (13)	0.0503 (5)
H18A	0.1151	−0.3052	0.419	0.075*
H18B	−0.0247	−0.3829	0.4359	0.075*
H18C	0.1071	−0.4021	0.4836	0.075*
C19	0.03676 (18)	−0.27803 (18)	0.61657 (13)	0.0458 (4)
H19A	−0.0601	−0.327	0.585	0.069*
H19B	0.0516	−0.205	0.6675	0.069*
H19C	0.0734	−0.3373	0.64	0.069*
C20	0.05301 (19)	−0.1242 (2)	0.51307 (14)	0.0495 (5)
H20A	0.0705	−0.0513	0.5649	0.074*
H20B	−0.0443	−0.1713	0.4826	0.074*
H20C	0.0974	−0.0891	0.4698	0.074*
C21	0.58891 (17)	−0.19560 (18)	0.56883 (12)	0.0414 (4)
C25	0.09512 (16)	0.28072 (16)	0.79279 (11)	0.0334 (3)
C26	−0.03540 (17)	0.22322 (16)	0.80045 (12)	0.0406 (4)
H26	−0.0763	0.1312	0.7942	0.049*
C27	−0.10495 (16)	0.30261 (16)	0.81741 (12)	0.0385 (4)
H27	−0.1921	0.2638	0.8236	0.046*
C28	−0.04634 (15)	0.43969 (15)	0.82533 (11)	0.0310 (3)
C29	0.08501 (15)	0.49289 (15)	0.81665 (10)	0.0300 (3)
H29	0.1251	0.5846	0.8218	0.036*
C30	0.16077 (15)	0.41736 (15)	0.80073 (10)	0.0294 (3)
C31	−0.12629 (16)	0.52644 (17)	0.84061 (12)	0.0371 (4)
C32	−0.1880 (2)	0.5004 (2)	0.91925 (15)	0.0562 (5)
H32A	−0.2375	0.5556	0.9278	0.084*
H32B	−0.1156	0.5223	0.9759	0.084*
H32C	−0.2498	0.4071	0.9035	0.084*
C33	−0.0344 (2)	0.6768 (2)	0.8677 (2)	0.0792 (8)
H33A	0.0028	0.698	0.8184	0.119*
H33B	0.0394	0.6995	0.9237	0.119*
H33C	−0.0876	0.7274	0.8781	0.119*
C34	−0.2414 (3)	0.4900 (3)	0.75103 (16)	0.0823 (8)
H34A	−0.203	0.5063	0.7014	0.124*
H34B	−0.2919	0.5442	0.7592	0.124*
H34C	−0.3022	0.3964	0.7358	0.124*
C35	0.30789 (15)	0.48317 (16)	0.79499 (11)	0.0352 (4)
C36	0.40825 (18)	0.4698 (2)	0.87618 (14)	0.0540 (5)
H36A	0.5008	0.517	0.876	0.081*
H36B	0.389	0.3762	0.8696	0.081*
H36C	0.398	0.5077	0.9339	0.081*
C37	0.31886 (19)	0.4175 (2)	0.70201 (13)	0.0485 (4)
H37A	0.2603	0.4318	0.6517	0.073*
H37B	0.2908	0.3224	0.6945	0.073*
H37C	0.4124	0.4571	0.7017	0.073*
C38	0.35244 (18)	0.63396 (18)	0.80263 (15)	0.0504 (5)
H38A	0.29	0.6458	0.7532	0.076*
H38B	0.4437	0.6712	0.7979	0.076*
H38C	0.3515	0.6793	0.8616	0.076*
N1	0.36199 (18)	−0.15552 (17)	1.04487 (12)	0.0546 (4)
N2	0.1971 (3)	0.0875 (3)	1.13809 (15)	0.0937 (8)
O1	0.24505 (12)	0.02227 (11)	0.70557 (8)	0.0384 (3)
O2	0.15855 (12)	0.19450 (11)	0.76953 (8)	0.0400 (3)
C22A	0.7447 (3)	−0.1104 (4)	0.6219 (2)	0.0569 (8)	0.814 (6)
H22A	0.7633	−0.1136	0.6856	0.085*	0.814 (6)
H22B	0.7686	−0.0186	0.6198	0.085*	0.814 (6)
H22C	0.7982	−0.1465	0.593	0.085*	0.814 (6)
C23A	0.5683 (3)	−0.1892 (5)	0.46811 (18)	0.0696 (12)	0.814 (6)
H23A	0.6292	−0.2192	0.4438	0.104*	0.814 (6)
H23B	0.5879	−0.0981	0.4658	0.104*	0.814 (6)
H23C	0.4748	−0.2464	0.4314	0.104*	0.814 (6)
C24A	0.5532 (5)	−0.3364 (4)	0.5778 (5)	0.0921 (16)	0.814 (6)
H24A	0.6091	−0.3733	0.5526	0.138*	0.814 (6)
H24B	0.4579	−0.3913	0.5441	0.138*	0.814 (6)
H24C	0.5696	−0.3348	0.6423	0.138*	0.814 (6)
C22B	0.5042 (14)	−0.2940 (15)	0.4618 (7)	0.050 (3)	0.186 (6)
H22D	0.5663	−0.3179	0.4347	0.075*	0.186 (6)
H22E	0.4646	−0.2471	0.425	0.075*	0.186 (6)
H22F	0.4323	−0.3743	0.4633	0.075*	0.186 (6)
C23B	0.6083 (13)	−0.2968 (14)	0.6183 (9)	0.0414 (4)	0.186 (6)
H23D	0.664	−0.3346	0.5936	0.062*	0.186 (6)
H23E	0.5203	−0.3674	0.6093	0.062*	0.186 (6)
H23F	0.653	−0.2532	0.6837	0.062*	0.186 (6)
C24B	0.7055 (16)	−0.0922 (14)	0.5672 (16)	0.075 (5)	0.186 (6)
H24D	0.7568	−0.0353	0.6294	0.112*	0.186 (6)
H24E	0.6791	−0.04	0.5286	0.112*	0.186 (6)
H24F	0.7615	−0.1295	0.5424	0.112*	0.186 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0435 (9)	0.0387 (9)	0.0422 (10)	0.0193 (8)	0.0179 (8)	0.0111 (8)
C2	0.0913 (16)	0.0783 (14)	0.0484 (12)	0.0639 (13)	0.0374 (11)	0.0255 (11)
C3	0.0367 (8)	0.0329 (8)	0.0402 (9)	0.0163 (7)	0.0168 (7)	0.0114 (7)
C4	0.0487 (9)	0.0455 (9)	0.0374 (10)	0.0275 (8)	0.0209 (8)	0.0120 (8)
C5	0.0564 (10)	0.0455 (10)	0.0435 (10)	0.0343 (9)	0.0254 (8)	0.0112 (8)
C6	0.0411 (8)	0.0319 (8)	0.0388 (9)	0.0208 (7)	0.0184 (7)	0.0099 (7)
C7	0.0371 (8)	0.0290 (7)	0.0362 (9)	0.0164 (6)	0.0180 (7)	0.0059 (6)
C8	0.0411 (8)	0.0318 (8)	0.0425 (10)	0.0208 (7)	0.0202 (7)	0.0091 (7)
C11	0.0445 (9)	0.0340 (8)	0.0359 (9)	0.0234 (7)	0.0224 (7)	0.0100 (7)
C12	0.0461 (9)	0.0396 (9)	0.0378 (10)	0.0166 (8)	0.0173 (8)	−0.0005 (7)
C13	0.0366 (8)	0.0496 (10)	0.0378 (10)	0.0167 (8)	0.0149 (7)	0.0042 (8)
C14	0.0397 (8)	0.0394 (9)	0.0332 (9)	0.0209 (7)	0.0200 (7)	0.0116 (7)
C15	0.0418 (8)	0.0324 (8)	0.0318 (8)	0.0191 (7)	0.0166 (7)	0.0069 (7)
C16	0.0383 (8)	0.0310 (8)	0.0348 (9)	0.0189 (6)	0.0176 (7)	0.0126 (7)
C17	0.0384 (8)	0.0378 (8)	0.0398 (9)	0.0203 (7)	0.0157 (7)	0.0125 (7)
C18	0.0424 (10)	0.0524 (11)	0.0477 (11)	0.0187 (8)	0.0093 (8)	0.0010 (9)
C19	0.0422 (9)	0.0455 (10)	0.0548 (12)	0.0171 (8)	0.0226 (8)	0.0187 (9)
C20	0.0474 (10)	0.0566 (11)	0.0579 (12)	0.0305 (9)	0.0182 (9)	0.0262 (10)
C21	0.0431 (9)	0.0505 (10)	0.0425 (10)	0.0268 (8)	0.0239 (8)	0.0111 (8)
C25	0.0409 (8)	0.0361 (8)	0.0316 (8)	0.0247 (7)	0.0142 (7)	0.0061 (7)
C26	0.0433 (9)	0.0299 (8)	0.0481 (11)	0.0149 (7)	0.0171 (8)	0.0061 (7)
C27	0.0319 (8)	0.0369 (9)	0.0446 (10)	0.0131 (7)	0.0140 (7)	0.0056 (7)
C28	0.0316 (7)	0.0362 (8)	0.0296 (8)	0.0189 (6)	0.0108 (6)	0.0069 (6)
C29	0.0320 (7)	0.0314 (8)	0.0306 (8)	0.0167 (6)	0.0113 (6)	0.0078 (6)
C30	0.0322 (7)	0.0365 (8)	0.0242 (8)	0.0192 (6)	0.0097 (6)	0.0071 (6)
C31	0.0359 (8)	0.0433 (9)	0.0433 (10)	0.0252 (7)	0.0173 (7)	0.0132 (8)
C32	0.0628 (12)	0.0676 (13)	0.0641 (14)	0.0428 (11)	0.0377 (11)	0.0227 (11)
C33	0.0718 (14)	0.0479 (12)	0.150 (3)	0.0396 (11)	0.0676 (16)	0.0295 (14)
C34	0.0867 (17)	0.133 (2)	0.0566 (15)	0.0862 (18)	0.0123 (12)	0.0214 (15)
C35	0.0315 (7)	0.0435 (9)	0.0369 (9)	0.0209 (7)	0.0142 (7)	0.0097 (7)
C36	0.0365 (9)	0.0752 (14)	0.0522 (12)	0.0262 (9)	0.0092 (8)	0.0212 (10)
C37	0.0474 (10)	0.0597 (12)	0.0464 (11)	0.0251 (9)	0.0264 (9)	0.0115 (9)
C38	0.0397 (9)	0.0461 (10)	0.0706 (14)	0.0170 (8)	0.0276 (9)	0.0161 (10)
N1	0.0664 (11)	0.0530 (10)	0.0526 (10)	0.0305 (8)	0.0185 (8)	0.0214 (8)
N2	0.160 (2)	0.137 (2)	0.0594 (13)	0.1165 (19)	0.0640 (14)	0.0490 (13)
O1	0.0530 (7)	0.0419 (6)	0.0368 (7)	0.0314 (6)	0.0243 (5)	0.0116 (5)
O2	0.0580 (7)	0.0415 (6)	0.0394 (7)	0.0352 (6)	0.0242 (6)	0.0129 (5)
C22A	0.0425 (14)	0.089 (2)	0.0473 (17)	0.0339 (14)	0.0231 (13)	0.0108 (15)
C23A	0.0579 (18)	0.117 (3)	0.0391 (15)	0.046 (2)	0.0224 (13)	0.0008 (17)
C24A	0.075 (2)	0.054 (2)	0.178 (5)	0.0412 (18)	0.072 (3)	0.033 (3)
C22B	0.066 (8)	0.061 (8)	0.037 (6)	0.044 (7)	0.023 (5)	0.000 (5)
C23B	0.0431 (9)	0.0505 (10)	0.0425 (10)	0.0268 (8)	0.0239 (8)	0.0111 (8)
C24B	0.059 (9)	0.071 (8)	0.105 (15)	0.029 (7)	0.055 (10)	0.007 (9)

C1—N1	1.145 (2)	C27—C28	1.388 (2)
C1—C3	1.438 (2)	C27—H27	0.93
C2—N2	1.143 (3)	C28—C29	1.392 (2)
C2—C4	1.434 (3)	C28—C31	1.534 (2)
C3—C8	1.383 (2)	C29—C30	1.3999 (19)
C3—C4	1.395 (2)	C29—H29	0.93
C4—C5	1.393 (2)	C30—C35	1.542 (2)
C5—C6	1.376 (2)	C31—C34	1.518 (3)
C5—H5	0.93	C31—C33	1.525 (3)
C6—O2	1.3578 (19)	C31—C32	1.528 (2)
C6—C7	1.412 (2)	C32—H32A	0.96
C7—O1	1.3588 (19)	C32—H32B	0.96
C7—C8	1.376 (2)	C32—H32C	0.96
C8—H8	0.93	C33—H33A	0.96
C11—C12	1.379 (2)	C33—H33B	0.96
C11—C16	1.393 (2)	C33—H33C	0.96
C11—O1	1.4110 (17)	C34—H34A	0.96
C12—C13	1.384 (2)	C34—H34B	0.96
C12—H12	0.93	C34—H34C	0.96
C13—C14	1.383 (2)	C35—C36	1.529 (2)
C13—H13	0.93	C35—C38	1.533 (2)
C14—C15	1.394 (2)	C35—C37	1.536 (2)
C14—C21	1.532 (2)	C36—H36A	0.96
C15—C16	1.397 (2)	C36—H36B	0.96
C15—H15	0.93	C36—H36C	0.96
C16—C17	1.536 (2)	C37—H37A	0.96
C17—C18	1.529 (2)	C37—H37B	0.96
C17—C20	1.531 (2)	C37—H37C	0.96
C17—C19	1.539 (2)	C38—H38A	0.96
C18—H18A	0.96	C38—H38B	0.96
C18—H18B	0.96	C38—H38C	0.96
C18—H18C	0.96	C22A—H22A	0.96
C19—H19A	0.96	C22A—H22B	0.96
C19—H19B	0.96	C22A—H22C	0.96
C19—H19C	0.96	C23A—H23A	0.96
C20—H20A	0.96	C23A—H23B	0.96
C20—H20B	0.96	C23A—H23C	0.96
C20—H20C	0.96	C24A—H24A	0.96
C21—C24B	1.384 (13)	C24A—H24B	0.96
C21—C24A	1.500 (4)	C24A—H24C	0.96
C21—C23B	1.501 (12)	C22B—H22D	0.96
C21—C23A	1.525 (3)	C22B—H22E	0.96
C21—C22A	1.557 (3)	C22B—H22F	0.96
C21—C22B	1.650 (11)	C23B—H23D	0.96
C25—C26	1.382 (2)	C23B—H23E	0.96
C25—C30	1.390 (2)	C23B—H23F	0.96
C25—O2	1.4089 (17)	C24B—H24D	0.96
C26—C27	1.380 (2)	C24B—H24E	0.96
C26—H26	0.93	C24B—H24F	0.96
N1—C1—C3	179.26 (18)	C26—C27—C28	120.78 (15)
N2—C2—C4	178.4 (3)	C26—C27—H27	119.6
C8—C3—C4	119.70 (15)	C28—C27—H27	119.6
C8—C3—C1	120.12 (14)	C27—C28—C29	117.23 (13)
C4—C3—C1	120.18 (15)	C27—C28—C31	120.53 (13)
C5—C4—C3	120.20 (15)	C29—C28—C31	122.23 (14)
C5—C4—C2	120.12 (15)	C28—C29—C30	124.32 (14)
C3—C4—C2	119.67 (15)	C28—C29—H29	117.8
C6—C5—C4	119.99 (14)	C30—C29—H29	117.8
C6—C5—H5	120	C25—C30—C29	115.24 (13)
C4—C5—H5	120	C25—C30—C35	122.92 (13)
O2—C6—C5	125.57 (13)	C29—C30—C35	121.83 (14)
O2—C6—C7	114.72 (14)	C34—C31—C33	109.46 (19)
C5—C6—C7	119.68 (14)	C34—C31—C32	109.21 (17)
O1—C7—C8	124.80 (13)	C33—C31—C32	106.95 (16)
O1—C7—C6	115.18 (13)	C34—C31—C28	108.44 (14)
C8—C7—C6	120.00 (14)	C33—C31—C28	112.04 (14)
C7—C8—C3	120.42 (14)	C32—C31—C28	110.70 (13)
C7—C8—H8	119.8	C31—C32—H32A	109.5
C3—C8—H8	119.8	C31—C32—H32B	109.5
C12—C11—C16	122.65 (13)	H32A—C32—H32B	109.5
C12—C11—O1	117.89 (14)	C31—C32—H32C	109.5
C16—C11—O1	119.32 (14)	H32A—C32—H32C	109.5
C11—C12—C13	120.01 (16)	H32B—C32—H32C	109.5
C11—C12—H12	120	C31—C33—H33A	109.5
C13—C12—H12	120	C31—C33—H33B	109.5
C14—C13—C12	120.56 (16)	H33A—C33—H33B	109.5
C14—C13—H13	119.7	C31—C33—H33C	109.5
C12—C13—H13	119.7	H33A—C33—H33C	109.5
C13—C14—C15	117.32 (14)	H33B—C33—H33C	109.5
C13—C14—C21	122.73 (15)	C31—C34—H34A	109.5
C15—C14—C21	119.95 (14)	C31—C34—H34B	109.5
C14—C15—C16	124.54 (15)	H34A—C34—H34B	109.5
C14—C15—H15	117.7	C31—C34—H34C	109.5
C16—C15—H15	117.7	H34A—C34—H34C	109.5
C11—C16—C15	114.91 (14)	H34B—C34—H34C	109.5
C11—C16—C17	123.53 (13)	C36—C35—C38	107.50 (15)
C15—C16—C17	121.56 (14)	C36—C35—C37	110.04 (14)
C18—C17—C20	107.50 (15)	C38—C35—C37	107.12 (14)
C18—C17—C16	111.47 (13)	C36—C35—C30	109.04 (14)
C20—C17—C16	111.28 (14)	C38—C35—C30	111.76 (12)
C18—C17—C19	108.14 (15)	C37—C35—C30	111.30 (14)
C20—C17—C19	109.01 (14)	C35—C36—H36A	109.5
C16—C17—C19	109.35 (14)	C35—C36—H36B	109.5
C17—C18—H18A	109.5	H36A—C36—H36B	109.5
C17—C18—H18B	109.5	C35—C36—H36C	109.5
H18A—C18—H18B	109.5	H36A—C36—H36C	109.5
C17—C18—H18C	109.5	H36B—C36—H36C	109.5
H18A—C18—H18C	109.5	C35—C37—H37A	109.5
H18B—C18—H18C	109.5	C35—C37—H37B	109.5
C17—C19—H19A	109.5	H37A—C37—H37B	109.5
C17—C19—H19B	109.5	C35—C37—H37C	109.5
H19A—C19—H19B	109.5	H37A—C37—H37C	109.5
C17—C19—H19C	109.5	H37B—C37—H37C	109.5
H19A—C19—H19C	109.5	C35—C38—H38A	109.5
H19B—C19—H19C	109.5	C35—C38—H38B	109.5
C17—C20—H20A	109.5	H38A—C38—H38B	109.5
C17—C20—H20B	109.5	C35—C38—H38C	109.5
H20A—C20—H20B	109.5	H38A—C38—H38C	109.5
C17—C20—H20C	109.5	H38B—C38—H38C	109.5
H20A—C20—H20C	109.5	C7—O1—C11	118.38 (12)
H20B—C20—H20C	109.5	C6—O2—C25	120.00 (12)
C24B—C21—C24A	135.6 (7)	C21—C22A—H22A	109.5
C24B—C21—C23B	117.8 (9)	C21—C22A—H22B	109.5
C24A—C21—C23B	27.0 (4)	C21—C22A—H22C	109.5
C24B—C21—C23A	72.6 (9)	C21—C23A—H23A	109.5
C24A—C21—C23A	112.7 (3)	C21—C23A—H23B	109.5
C23B—C21—C23A	133.6 (5)	C21—C23A—H23C	109.5
C24B—C21—C14	110.0 (5)	C21—C24A—H24A	109.5
C24A—C21—C14	109.31 (17)	C21—C24A—H24B	109.5
C23B—C21—C14	108.7 (5)	C21—C24A—H24C	109.5
C23A—C21—C14	108.60 (16)	C21—C22B—H22D	109.5
C24B—C21—C22A	36.7 (9)	C21—C22B—H22E	109.5
C24A—C21—C22A	108.2 (2)	H22D—C22B—H22E	109.5
C23B—C21—C22A	84.1 (5)	C21—C22B—H22F	109.5
C23A—C21—C22A	106.40 (19)	H22D—C22B—H22F	109.5
C14—C21—C22A	111.68 (16)	H22E—C22B—H22F	109.5
C24B—C21—C22B	108.7 (8)	C21—C23B—H23D	109.5
C24A—C21—C22B	75.0 (5)	C21—C23B—H23E	109.5
C23B—C21—C22B	100.4 (6)	H23D—C23B—H23E	109.5
C23A—C21—C22B	40.0 (5)	C21—C23B—H23F	109.5
C14—C21—C22B	110.8 (4)	H23D—C23B—H23F	109.5
C22A—C21—C22B	133.0 (4)	H23E—C23B—H23F	109.5
C26—C25—C30	122.53 (13)	C21—C24B—H24D	109.5
C26—C25—O2	117.88 (14)	C21—C24B—H24E	109.5
C30—C25—O2	119.43 (13)	H24D—C24B—H24E	109.5
C27—C26—C25	119.90 (15)	C21—C24B—H24F	109.5
C27—C26—H26	120	H24D—C24B—H24F	109.5
C25—C26—H26	120	H24E—C24B—H24F	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19B···O1	0.96	2.5	3.117 (2)	122
C20—H20A···O1	0.96	2.32	2.982 (3)	125
C36—H36B···O2	0.96	2.52	3.122 (3)	121
C37—H37B···O2	0.96	2.29	2.966 (2)	127
C22A—H22A···N2i	0.96	2.59	3.535 (4)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19B⋯O1	0.96	2.5	3.117 (2)	122
C20—H20A⋯O1	0.96	2.32	2.982 (3)	125
C36—H36B⋯O2	0.96	2.52	3.122 (3)	121
C37—H37B⋯O2	0.96	2.29	2.966 (2)	127
C22A—H22A⋯N2i	0.96	2.59	3.535 (4)	170

Symmetry code: (i) .