(E)-4-tert-Butyl-2-(2,6-diisopropyl-phenyl-imino-meth-yl)-6-(morpholinometh-yl)phenol.

In the mol-ecule of the title compound, C(28)H(40)N(2)O(2), the tert-butyl group is disordered over two positions; site-occupation factors were kept fixed at 0.5. The morpholine ring has a chair conformation. Intra-molecular O-H⋯N hydrogen bonding results in the formation of a planar six-membered ring, which is oriented at a dihedral angle of 0.70 (3)° with respect to the adjacent aromatic ring. The dihedral angle between the benzene rings is 67.66 (3)°.

Related literature

For general background, see: Younkin et al. (2000 ▶); Gibson & Spitzmesser (2003 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C28H40N2O2

M = 436.62

Orthorhombic,

a = 10.086 (2) Å

b = 20.394 (4) Å

c = 12.750 (3) Å

V = 2622.8 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 113 (2) K

0.12 × 0.10 × 0.06 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.992, T max = 0.996

25483 measured reflections

4618 independent reflections

4314 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.095

S = 1.04

4618 reflections

318 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.13 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808007204/hk2432sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808007204/hk2432Isup2.hkl

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

C28H40N2O2	Dx = 1.106 Mg m−3
Mr = 436.62	Melting point: 364 K
Orthorhombic, Pna21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 5337 reflections
a = 10.086 (2) Å	θ = 1.9–29.7º
b = 20.394 (4) Å	µ = 0.07 mm−1
c = 12.750 (3) Å	T = 113 (2) K
V = 2622.8 (10) Å3	Block, yellow
Z = 4	0.12 × 0.10 × 0.06 mm
F000 = 952

Rigaku Saturn diffractometer	4314 reflections with I > 2σ(I)
Monochromator: confocal	Rint = 0.040
T = 294(2) K	θmax = 25.0º
ω scans	θmin = 2.3º
Absorption correction: multi-scan(Blessing, 1995)	h = −12→11
Tmin = 0.992, Tmax = 0.996	k = −24→24
25483 measured reflections	l = −15→15
4618 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.037	w = 1/[σ2(Fo2) + (0.0588P)2 + 0.2207P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.095	(Δ/σ)max = 0.002
S = 1.04	Δρmax = 0.18 e Å−3
4618 reflections	Δρmin = −0.13 e Å−3
318 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0157 (15)
Secondary atom site location: difference Fourier map

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	Occ. (<1)
O1	0.66312 (13)	0.02738 (7)	0.58337 (11)	0.0474 (4)
O2	0.44036 (11)	0.16255 (6)	1.01270 (9)	0.0279 (3)
H2	0.4303	0.1919	1.0559	0.042*
N1	0.47500 (13)	0.04647 (6)	0.74844 (11)	0.0265 (3)
N2	0.32848 (13)	0.25917 (7)	1.10594 (11)	0.0280 (3)
C1	0.53145 (19)	0.10072 (9)	0.68955 (16)	0.0403 (5)
H1A	0.6101	0.1168	0.7251	0.048*
H1B	0.4678	0.1363	0.6857	0.048*
C2	0.5673 (2)	0.07857 (11)	0.58034 (18)	0.0527 (6)
H2A	0.4883	0.0632	0.5447	0.063*
H2B	0.6025	0.1154	0.5410	0.063*
C3	0.6091 (2)	−0.02659 (9)	0.63968 (16)	0.0406 (5)
H3A	0.6740	−0.0616	0.6427	0.049*
H3B	0.5317	−0.0430	0.6028	0.049*
C4	0.57015 (19)	−0.00743 (9)	0.74948 (15)	0.0355 (4)
H4A	0.5314	−0.0449	0.7848	0.043*
H4B	0.6485	0.0057	0.7882	0.043*
C5	0.44409 (19)	0.06580 (9)	0.85631 (14)	0.0352 (4)
H5A	0.5235	0.0834	0.8887	0.042*
H5B	0.4181	0.0271	0.8956	0.042*
C6	0.33465 (16)	0.11632 (8)	0.86387 (13)	0.0262 (4)
C7	0.33721 (15)	0.16278 (8)	0.94452 (12)	0.0234 (3)
C8	0.23469 (15)	0.20886 (8)	0.95331 (13)	0.0234 (3)
C9	0.12971 (16)	0.20779 (7)	0.88116 (13)	0.0247 (3)
H9A	0.0617	0.2383	0.8879	0.030*
C10	0.12458 (15)	0.16266 (7)	0.80036 (13)	0.0254 (4)
C11	0.22915 (16)	0.11738 (8)	0.79479 (13)	0.0260 (4)
H11A	0.2273	0.0863	0.7415	0.031*
C12	0.01307 (17)	0.16019 (8)	0.71896 (14)	0.0307 (4)
C13	−0.0397 (15)	0.0916 (5)	0.6974 (9)	0.071 (3)	0.50
H13A	−0.0129	0.0779	0.6285	0.106*	0.50
H13B	−0.1348	0.0919	0.7015	0.106*	0.50
H13C	−0.0049	0.0617	0.7485	0.106*	0.50
C14	0.0691 (10)	0.1924 (4)	0.6171 (6)	0.061 (2)	0.50
H14A	0.1041	0.2350	0.6334	0.092*	0.50
H14B	−0.0006	0.1966	0.5663	0.092*	0.50
H14C	0.1384	0.1654	0.5889	0.092*	0.50
C15	−0.1030 (10)	0.2032 (6)	0.7539 (9)	0.0307 (19)	0.50
H15A	−0.0786	0.2486	0.7479	0.046*	0.50
H15B	−0.1247	0.1935	0.8256	0.046*	0.50
H15C	−0.1785	0.1946	0.7102	0.046*	0.50
C13'	−0.0535 (11)	0.0920 (4)	0.7330 (8)	0.049 (2)	0.50
H13D	−0.0796	0.0865	0.8049	0.074*	0.50
H13E	0.0082	0.0582	0.7142	0.074*	0.50
H13F	−0.1303	0.0892	0.6888	0.074*	0.50
C14'	0.0708 (11)	0.1619 (4)	0.6092 (6)	0.063 (2)	0.50
H14D	0.1136	0.2033	0.5977	0.095*	0.50
H14E	0.0010	0.1562	0.5588	0.095*	0.50
H14F	0.1344	0.1271	0.6015	0.095*	0.50
C15'	−0.0942 (12)	0.2112 (6)	0.7301 (10)	0.046 (3)	0.50
H15D	−0.0563	0.2541	0.7220	0.069*	0.50
H15E	−0.1340	0.2077	0.7982	0.069*	0.50
H15F	−0.1605	0.2044	0.6772	0.069*	0.50
C16	0.23491 (16)	0.25686 (8)	1.03797 (13)	0.0264 (4)
H16A	0.1653	0.2866	1.0428	0.032*
C17	0.32130 (16)	0.30595 (9)	1.18948 (13)	0.0288 (4)
C18	0.30559 (17)	0.28018 (9)	1.29173 (15)	0.0327 (4)
C19	0.29501 (18)	0.32502 (10)	1.37352 (15)	0.0379 (4)
H19A	0.2815	0.3096	1.4413	0.045*
C20	0.3040 (2)	0.39149 (10)	1.35681 (15)	0.0409 (5)
H20A	0.2946	0.4205	1.4126	0.049*
C21	0.3271 (2)	0.41500 (9)	1.25706 (16)	0.0400 (5)
H21A	0.3356	0.4600	1.2470	0.048*
C22	0.33791 (17)	0.37310 (9)	1.17069 (15)	0.0331 (4)
C23	0.3753 (2)	0.40061 (9)	1.06383 (15)	0.0389 (5)
H23A	0.3678	0.3650	1.0126	0.047*
C24	0.5192 (2)	0.42388 (10)	1.06373 (17)	0.0443 (5)
H24A	0.5760	0.3885	1.0851	0.066*
H24B	0.5288	0.4599	1.1116	0.066*
H24C	0.5433	0.4378	0.9944	0.066*
C25	0.2825 (2)	0.45530 (12)	1.0295 (2)	0.0597 (6)
H25A	0.1927	0.4397	1.0304	0.090*
H25B	0.3052	0.4690	0.9597	0.090*
H25C	0.2910	0.4918	1.0766	0.090*
C26	0.29776 (18)	0.20684 (9)	1.30904 (15)	0.0373 (4)
H26A	0.3423	0.1858	1.2496	0.045*
C27	0.1547 (2)	0.18351 (11)	1.3088 (2)	0.0601 (6)
H27A	0.1120	0.1978	1.2455	0.090*
H27B	0.1092	0.2015	1.3683	0.090*
H27C	0.1527	0.1365	1.3123	0.090*
C28	0.3684 (2)	0.18417 (11)	1.40882 (18)	0.0525 (6)
H28A	0.4588	0.1988	1.4075	0.079*
H28B	0.3662	0.1372	1.4126	0.079*
H28C	0.3245	0.2023	1.4690	0.079*

	U11	U22	U33	U12	U13	U23
O1	0.0416 (8)	0.0574 (9)	0.0433 (8)	0.0162 (7)	0.0116 (7)	−0.0014 (7)
O2	0.0244 (6)	0.0340 (7)	0.0254 (6)	0.0025 (5)	−0.0045 (5)	−0.0040 (5)
N1	0.0278 (7)	0.0262 (7)	0.0254 (7)	0.0053 (6)	0.0026 (6)	−0.0005 (6)
N2	0.0264 (7)	0.0319 (7)	0.0259 (7)	−0.0017 (6)	−0.0010 (6)	−0.0038 (6)
C1	0.0386 (10)	0.0301 (9)	0.0523 (13)	0.0022 (8)	0.0144 (10)	0.0011 (8)
C2	0.0518 (12)	0.0587 (13)	0.0476 (13)	0.0186 (10)	0.0214 (11)	0.0139 (11)
C3	0.0388 (10)	0.0409 (10)	0.0421 (11)	0.0123 (8)	−0.0039 (9)	−0.0128 (9)
C4	0.0370 (9)	0.0323 (9)	0.0373 (10)	0.0112 (8)	−0.0018 (8)	−0.0023 (8)
C5	0.0361 (10)	0.0428 (10)	0.0267 (9)	0.0127 (8)	−0.0016 (8)	−0.0039 (8)
C6	0.0252 (8)	0.0300 (8)	0.0233 (8)	0.0032 (6)	0.0026 (7)	−0.0004 (7)
C7	0.0224 (8)	0.0275 (8)	0.0204 (8)	−0.0040 (6)	−0.0003 (7)	0.0030 (6)
C8	0.0227 (8)	0.0241 (8)	0.0235 (8)	−0.0035 (6)	0.0021 (7)	0.0003 (6)
C9	0.0218 (8)	0.0250 (8)	0.0271 (9)	0.0006 (6)	0.0011 (7)	−0.0020 (7)
C10	0.0236 (8)	0.0291 (8)	0.0234 (8)	−0.0026 (6)	0.0020 (7)	−0.0013 (7)
C11	0.0296 (9)	0.0257 (8)	0.0227 (8)	−0.0010 (6)	0.0002 (7)	−0.0034 (7)
C12	0.0269 (8)	0.0373 (9)	0.0281 (9)	0.0023 (7)	−0.0035 (7)	−0.0084 (7)
C13	0.069 (5)	0.051 (4)	0.092 (7)	0.011 (3)	−0.032 (5)	−0.040 (4)
C14	0.042 (3)	0.118 (6)	0.024 (3)	0.011 (4)	−0.008 (2)	0.005 (3)
C15	0.031 (3)	0.035 (4)	0.026 (4)	0.005 (2)	−0.017 (2)	−0.001 (2)
C13'	0.041 (4)	0.034 (3)	0.072 (5)	0.001 (2)	−0.045 (4)	−0.017 (3)
C14'	0.044 (3)	0.109 (6)	0.036 (3)	0.009 (4)	−0.005 (2)	0.002 (4)
C15'	0.057 (4)	0.035 (4)	0.045 (6)	0.014 (3)	−0.017 (3)	−0.006 (4)
C16	0.0256 (8)	0.0252 (8)	0.0285 (9)	−0.0029 (6)	0.0005 (7)	−0.0022 (7)
C17	0.0242 (8)	0.0360 (9)	0.0261 (9)	−0.0023 (7)	−0.0027 (7)	−0.0071 (7)
C18	0.0262 (9)	0.0412 (10)	0.0306 (10)	−0.0007 (7)	−0.0020 (8)	−0.0046 (8)
C19	0.0355 (9)	0.0514 (11)	0.0267 (9)	−0.0003 (8)	0.0009 (8)	−0.0082 (9)
C20	0.0445 (11)	0.0454 (11)	0.0330 (11)	−0.0009 (9)	0.0032 (9)	−0.0143 (9)
C21	0.0484 (11)	0.0324 (9)	0.0392 (11)	−0.0010 (8)	−0.0012 (9)	−0.0095 (8)
C22	0.0349 (9)	0.0350 (9)	0.0295 (9)	−0.0026 (7)	−0.0029 (8)	−0.0047 (7)
C23	0.0489 (11)	0.0355 (10)	0.0323 (10)	−0.0052 (8)	−0.0032 (9)	−0.0072 (8)
C24	0.0429 (11)	0.0461 (11)	0.0440 (11)	0.0007 (9)	0.0053 (10)	−0.0051 (9)
C25	0.0538 (13)	0.0767 (16)	0.0485 (13)	0.0090 (12)	−0.0107 (11)	0.0142 (12)
C26	0.0377 (10)	0.0422 (10)	0.0319 (10)	0.0010 (8)	0.0023 (9)	−0.0007 (9)
C27	0.0497 (13)	0.0569 (13)	0.0738 (17)	−0.0160 (11)	−0.0136 (13)	0.0043 (13)
C28	0.0514 (12)	0.0545 (13)	0.0516 (13)	−0.0024 (10)	−0.0053 (11)	0.0130 (11)

O1—C3	1.423 (3)	C14—H14C	0.9600
O1—C2	1.423 (2)	C15—H15A	0.9600
O2—C7	1.3558 (19)	C15—H15B	0.9600
O2—H2	0.8200	C15—H15C	0.9600
N1—C1	1.453 (2)	C13'—H13D	0.9600
N1—C4	1.459 (2)	C13'—H13E	0.9600
N1—C5	1.464 (2)	C13'—H13F	0.9600
N2—C16	1.282 (2)	C14'—H14D	0.9600
N2—C17	1.432 (2)	C14'—H14E	0.9600
C1—C2	1.508 (3)	C14'—H14F	0.9600
C1—H1A	0.9700	C15'—H15D	0.9600
C1—H1B	0.9700	C15'—H15E	0.9600
C2—H2A	0.9700	C15'—H15F	0.9600
C2—H2B	0.9700	C16—H16A	0.9300
C3—C4	1.506 (3)	C17—C22	1.400 (3)
C3—H3A	0.9700	C17—C18	1.415 (3)
C3—H3B	0.9700	C18—C19	1.391 (3)
C4—H4A	0.9700	C18—C26	1.514 (3)
C4—H4B	0.9700	C19—C20	1.375 (3)
C5—C6	1.513 (2)	C19—H19A	0.9300
C5—H5A	0.9700	C20—C21	1.379 (3)
C5—H5B	0.9700	C20—H20A	0.9300
C6—C11	1.382 (2)	C21—C22	1.398 (3)
C6—C7	1.398 (2)	C21—H21A	0.9300
C7—C8	1.402 (2)	C22—C23	1.521 (3)
C8—C9	1.403 (2)	C23—C25	1.521 (3)
C8—C16	1.457 (2)	C23—C24	1.527 (3)
C9—C10	1.382 (2)	C23—H23A	0.9800
C9—H9A	0.9300	C24—H24A	0.9600
C10—C11	1.404 (2)	C24—H24B	0.9600
C10—C12	1.531 (2)	C24—H24C	0.9600
C11—H11A	0.9300	C25—H25A	0.9600
C12—C15'	1.508 (8)	C25—H25B	0.9600
C12—C14'	1.517 (7)	C25—H25C	0.9600
C12—C13	1.522 (8)	C26—C27	1.519 (3)
C12—C15	1.530 (7)	C26—C28	1.530 (3)
C12—C13'	1.554 (7)	C26—H26A	0.9800
C12—C14	1.561 (7)	C27—H27A	0.9600
C13—H13A	0.9600	C27—H27B	0.9600
C13—H13B	0.9600	C27—H27C	0.9600
C13—H13C	0.9600	C28—H28A	0.9600
C14—H14A	0.9600	C28—H28B	0.9600
C14—H14B	0.9600	C28—H28C	0.9600
C3—O1—C2	108.71 (14)	H14B—C14—H14C	109.5
C7—O2—H2	109.5	C12—C15—H15A	109.5
C1—N1—C4	108.69 (14)	C12—C15—H15B	109.5
C1—N1—C5	111.33 (14)	H15A—C15—H15B	109.5
C4—N1—C5	109.53 (13)	C12—C15—H15C	109.5
C16—N2—C17	119.34 (13)	H15A—C15—H15C	109.5
N1—C1—C2	110.06 (16)	H15B—C15—H15C	109.5
N1—C1—H1A	109.6	C12—C13'—H13D	109.5
C2—C1—H1A	109.6	C12—C13'—H13E	109.5
N1—C1—H1B	109.6	H13D—C13'—H13E	109.5
C2—C1—H1B	109.6	C12—C13'—H13F	109.5
H1A—C1—H1B	108.2	H13D—C13'—H13F	109.5
O1—C2—C1	110.94 (17)	H13E—C13'—H13F	109.5
O1—C2—H2A	109.5	C12—C14'—H14D	109.5
C1—C2—H2A	109.5	C12—C14'—H14E	109.5
O1—C2—H2B	109.5	H14D—C14'—H14E	109.5
C1—C2—H2B	109.5	C12—C14'—H14F	109.5
H2A—C2—H2B	108.0	H14D—C14'—H14F	109.5
O1—C3—C4	111.61 (15)	H14E—C14'—H14F	109.5
O1—C3—H3A	109.3	C12—C15'—H15D	109.5
C4—C3—H3A	109.3	C12—C15'—H15E	109.5
O1—C3—H3B	109.3	H15D—C15'—H15E	109.5
C4—C3—H3B	109.3	C12—C15'—H15F	109.5
H3A—C3—H3B	108.0	H15D—C15'—H15F	109.5
N1—C4—C3	111.01 (15)	H15E—C15'—H15F	109.5
N1—C4—H4A	109.4	N2—C16—C8	121.77 (14)
C3—C4—H4A	109.4	N2—C16—H16A	119.1
N1—C4—H4B	109.4	C8—C16—H16A	119.1
C3—C4—H4B	109.4	C22—C17—C18	122.30 (15)
H4A—C4—H4B	108.0	C22—C17—N2	121.22 (15)
N1—C5—C6	113.49 (14)	C18—C17—N2	116.34 (15)
N1—C5—H5A	108.9	C19—C18—C17	117.09 (16)
C6—C5—H5A	108.9	C19—C18—C26	122.42 (17)
N1—C5—H5B	108.9	C17—C18—C26	120.48 (15)
C6—C5—H5B	108.9	C20—C19—C18	121.78 (18)
H5A—C5—H5B	107.7	C20—C19—H19A	119.1
C11—C6—C7	118.20 (14)	C18—C19—H19A	119.1
C11—C6—C5	122.14 (15)	C19—C20—C21	119.79 (17)
C7—C6—C5	119.65 (14)	C19—C20—H20A	120.1
O2—C7—C6	118.90 (14)	C21—C20—H20A	120.1
O2—C7—C8	121.14 (14)	C20—C21—C22	121.81 (18)
C6—C7—C8	119.95 (14)	C20—C21—H21A	119.1
C7—C8—C9	119.60 (14)	C22—C21—H21A	119.1
C7—C8—C16	120.56 (14)	C21—C22—C17	116.98 (18)
C9—C8—C16	119.83 (14)	C21—C22—C23	119.96 (16)
C10—C9—C8	121.83 (14)	C17—C22—C23	122.93 (16)
C10—C9—H9A	119.1	C25—C23—C22	112.08 (18)
C8—C9—H9A	119.1	C25—C23—C24	110.91 (17)
C9—C10—C11	116.59 (14)	C22—C23—C24	110.57 (16)
C9—C10—C12	123.67 (14)	C25—C23—H23A	107.7
C11—C10—C12	119.74 (14)	C22—C23—H23A	107.7
C6—C11—C10	123.83 (15)	C24—C23—H23A	107.7
C6—C11—H11A	118.1	C23—C24—H24A	109.5
C10—C11—H11A	118.1	C23—C24—H24B	109.5
C15'—C12—C14'	110.3 (6)	H24A—C24—H24B	109.5
C15'—C12—C13	113.6 (9)	C23—C24—H24C	109.5
C14'—C12—C13	89.3 (6)	H24A—C24—H24C	109.5
C14'—C12—C15	123.4 (6)	H24B—C24—H24C	109.5
C13—C12—C15	108.2 (8)	C23—C25—H25A	109.5
C15'—C12—C10	116.1 (6)	C23—C25—H25B	109.5
C14'—C12—C10	110.0 (5)	H25A—C25—H25B	109.5
C13—C12—C10	114.2 (6)	C23—C25—H25C	109.5
C15—C12—C10	110.2 (5)	H25A—C25—H25C	109.5
C15'—C12—C13'	107.2 (7)	H25B—C25—H25C	109.5
C14'—C12—C13'	107.0 (6)	C18—C26—C27	111.01 (17)
C15—C12—C13'	98.6 (7)	C18—C26—C28	113.29 (16)
C10—C12—C13'	105.6 (4)	C27—C26—C28	110.46 (18)
C15'—C12—C14	92.7 (6)	C18—C26—H26A	107.3
C13—C12—C14	111.3 (6)	C27—C26—H26A	107.3
C15—C12—C14	106.2 (6)	C28—C26—H26A	107.3
C10—C12—C14	106.5 (4)	C26—C27—H27A	109.5
C13'—C12—C14	129.0 (5)	C26—C27—H27B	109.5
C12—C13—H13A	109.5	H27A—C27—H27B	109.5
C12—C13—H13B	109.5	C26—C27—H27C	109.5
H13A—C13—H13B	109.5	H27A—C27—H27C	109.5
C12—C13—H13C	109.5	H27B—C27—H27C	109.5
H13A—C13—H13C	109.5	C26—C28—H28A	109.5
H13B—C13—H13C	109.5	C26—C28—H28B	109.5
C12—C14—H14A	109.5	H28A—C28—H28B	109.5
C12—C14—H14B	109.5	C26—C28—H28C	109.5
H14A—C14—H14B	109.5	H28A—C28—H28C	109.5
C12—C14—H14C	109.5	H28B—C28—H28C	109.5
H14A—C14—H14C	109.5
C4—N1—C1—C2	57.0 (2)	C9—C10—C12—C15	−12.5 (6)
C5—N1—C1—C2	177.71 (15)	C11—C10—C12—C15	167.6 (5)
C3—O1—C2—C1	60.1 (2)	C9—C10—C12—C13'	−118.0 (5)
N1—C1—C2—O1	−60.7 (2)	C11—C10—C12—C13'	62.1 (5)
C2—O1—C3—C4	−58.5 (2)	C9—C10—C12—C14	102.2 (4)
C1—N1—C4—C3	−55.6 (2)	C11—C10—C12—C14	−77.6 (4)
C5—N1—C4—C3	−177.41 (16)	C17—N2—C16—C8	−177.94 (15)
O1—C3—C4—N1	57.4 (2)	C7—C8—C16—N2	0.8 (2)
C1—N1—C5—C6	66.21 (19)	C9—C8—C16—N2	179.50 (15)
C4—N1—C5—C6	−173.56 (15)	C16—N2—C17—C22	−70.8 (2)
N1—C5—C6—C11	34.2 (2)	C16—N2—C17—C18	113.33 (18)
N1—C5—C6—C7	−147.46 (15)	C22—C17—C18—C19	5.7 (3)
C11—C6—C7—O2	−179.73 (14)	N2—C17—C18—C19	−178.39 (15)
C5—C6—C7—O2	1.8 (2)	C22—C17—C18—C26	−175.61 (16)
C11—C6—C7—C8	−0.2 (2)	N2—C17—C18—C26	0.3 (2)
C5—C6—C7—C8	−178.66 (15)	C17—C18—C19—C20	−2.2 (3)
O2—C7—C8—C9	179.79 (14)	C26—C18—C19—C20	179.14 (18)
C6—C7—C8—C9	0.3 (2)	C18—C19—C20—C21	−1.5 (3)
O2—C7—C8—C16	−1.5 (2)	C19—C20—C21—C22	1.9 (3)
C6—C7—C8—C16	178.97 (14)	C20—C21—C22—C17	1.4 (3)
C7—C8—C9—C10	−0.6 (2)	C20—C21—C22—C23	−174.63 (19)
C16—C8—C9—C10	−179.24 (15)	C18—C17—C22—C21	−5.3 (3)
C8—C9—C10—C11	0.7 (2)	N2—C17—C22—C21	179.01 (15)
C8—C9—C10—C12	−179.16 (15)	C18—C17—C22—C23	170.59 (17)
C7—C6—C11—C10	0.4 (2)	N2—C17—C22—C23	−5.1 (3)
C5—C6—C11—C10	178.80 (16)	C21—C22—C23—C25	−55.3 (2)
C9—C10—C11—C6	−0.6 (2)	C17—C22—C23—C25	128.9 (2)
C12—C10—C11—C6	179.22 (15)	C21—C22—C23—C24	69.0 (2)
C9—C10—C12—C15'	0.6 (6)	C17—C22—C23—C24	−106.78 (19)
C11—C10—C12—C15'	−179.2 (6)	C19—C18—C26—C27	85.8 (2)
C9—C10—C12—C14'	126.8 (4)	C17—C18—C26—C27	−92.8 (2)
C11—C10—C12—C14'	−53.0 (4)	C19—C18—C26—C28	−39.2 (3)
C9—C10—C12—C13	−134.6 (6)	C17—C18—C26—C28	142.27 (18)
C11—C10—C12—C13	45.6 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2	0.82	1.83	2.5630 (18)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N2	0.82	1.83	2.5630 (18)	148