4-Methyl-1,3-bis-(3,4-methyl-enedioxy-benz-yl)-2-(3,4-methyl-enedioxy-phen-yl)imidazolidine.

In the title compound, C(27)H(26)N(2)O(6), the imidazolidine ring adopts an envelope conformation. The methyl group on the imidazolidine ring is disordered over two positions with occupancies of 0.517 (11) and 0.483 (11), and the 3,4-methyl-enedioxy-phenyl at the 3-position of imidazolidine ring is also disordered over two positions with occupancies of 0.60 (2) and 0.40 (2).

Related literature

For biological activity of imidazolidine derivatives, see: Sasho et al. (1994 ▶). For related compounds, see: Xia et al. (2007 ▶); Iskenderov et al. (2009 ▶).

Experimental

Crystal data

C27H26N2O6

M = 474.50

Orthorhombic,

a = 11.586 (2) Å

b = 12.575 (3) Å

c = 32.749 (7) Å

V = 4771.3 (17) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.50 × 0.40 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.955, T max = 0.972

19793 measured reflections

4200 independent reflections

2896 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.215

S = 1.07

4200 reflections

392 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.43 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809046662/xu2638sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809046662/xu2638Isup2.hkl

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

C27H26N2O6	Dx = 1.321 Mg m−3
Mr = 474.50	Melting point: 478 K
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 4200 reflections
a = 11.586 (2) Å	θ = 1.2–25.0°
b = 12.575 (3) Å	µ = 0.09 mm−1
c = 32.749 (7) Å	T = 298 K
V = 4771.3 (17) Å3	Block, yellow
Z = 8	0.50 × 0.40 × 0.30 mm
F(000) = 2000

Bruker SMART CCD area-detector diffractometer	4200 independent reflections
Radiation source: fine-focus sealed tube	2896 reflections with I > 2σ(I)
graphite	Rint = 0.055
φ and ω scans	θmax = 25.0°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→12
Tmin = 0.955, Tmax = 0.972	k = −10→14
19793 measured reflections	l = −35→38

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.215	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.1256P)2 + 1.4629P] where P = (Fo2 + 2Fc2)/3
4200 reflections	(Δ/σ)max < 0.001
392 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

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)
N1	0.54794 (18)	0.07206 (19)	0.38949 (7)	0.0516 (6)
N2	0.65433 (19)	0.1297 (2)	0.33661 (7)	0.0560 (6)
O1	0.57024 (18)	0.60432 (18)	0.42342 (7)	0.0681 (6)
O2	0.48948 (18)	0.53485 (17)	0.36519 (6)	0.0675 (6)
O3	0.6527 (14)	0.3038 (15)	0.1842 (4)	0.103 (4)	0.60 (2)
O4	0.7802 (7)	0.1936 (14)	0.1522 (2)	0.111 (4)	0.60 (2)
O3'	0.671 (2)	0.346 (2)	0.1934 (7)	0.108 (6)	0.40 (2)
O4'	0.8033 (11)	0.2699 (19)	0.1568 (3)	0.105 (5)	0.40 (2)
O5	0.18733 (17)	−0.21867 (19)	0.47927 (7)	0.0725 (7)
O6	0.15747 (17)	−0.03598 (19)	0.45358 (8)	0.0790 (7)
C1	0.6424 (2)	0.1424 (2)	0.38092 (8)	0.0505 (7)
H1	0.7120	0.1146	0.3941	0.061*
C2	0.6315 (4)	0.0114 (3)	0.32760 (12)	0.0877 (12)
H2	0.7018	−0.0304	0.3232	0.105*	0.517 (11)
H2A	0.5912	0.0032	0.3018	0.105*	0.483 (11)
H2B	0.7035	−0.0278	0.3263	0.105*	0.483 (11)
C3	0.5571 (3)	−0.0288 (3)	0.36290 (12)	0.0814 (11)
H3A	0.5946	−0.0864	0.3775	0.098*	0.517 (11)
H3B	0.4819	−0.0523	0.3535	0.098*	0.517 (11)
H3	0.5801	−0.0952	0.3763	0.098*	0.483 (11)
C4	0.5461 (10)	0.0063 (10)	0.2920 (3)	0.137 (5)	0.517 (11)
H4A	0.5292	−0.0667	0.2858	0.206*	0.517 (11)
H4B	0.5793	0.0400	0.2685	0.206*	0.517 (11)
H4C	0.4761	0.0423	0.2994	0.206*	0.517 (11)
C4'	0.4468 (10)	−0.0296 (10)	0.3372 (3)	0.137 (5)	0.483 (11)
H4'1	0.4419	0.0352	0.3218	0.206*	0.483 (11)
H4'2	0.3809	−0.0354	0.3548	0.206*	0.483 (11)
H4'3	0.4485	−0.0890	0.3188	0.206*	0.483 (11)
C5	0.6280 (2)	0.2673 (2)	0.39295 (8)	0.0452 (7)
C6	0.5621 (2)	0.3386 (2)	0.36982 (8)	0.0485 (7)
H6	0.5268	0.3156	0.3459	0.058*
C7	0.5486 (2)	0.4488 (2)	0.38306 (8)	0.0491 (7)
C8	0.5974 (2)	0.4909 (2)	0.41752 (8)	0.0491 (7)
C9	0.6641 (2)	0.4241 (3)	0.44031 (9)	0.0559 (8)
H9	0.7001	0.4489	0.4638	0.067*
C10	0.6793 (2)	0.3109 (2)	0.42730 (8)	0.0504 (7)
H10	0.7258	0.2672	0.4432	0.060*
C11	0.4924 (3)	0.6290 (3)	0.39238 (10)	0.0693 (9)
H11A	0.5178	0.6915	0.3775	0.083*
H11B	0.4164	0.6429	0.4036	0.083*
C12	0.7609 (3)	0.1641 (3)	0.32329 (10)	0.0744 (10)
H12A	0.8188	0.1132	0.3320	0.089*
H12B	0.7783	0.2314	0.3364	0.089*
C13	0.771 (16)	0.18 (2)	0.276 (5)	0.078 (13)	0.60 (2)
C14	0.8314 (9)	0.0937 (14)	0.2552 (4)	0.090 (3)	0.60 (2)
H14	0.8619	0.0364	0.2695	0.108*	0.60 (2)
C15	0.8420 (10)	0.1013 (14)	0.2130 (3)	0.099 (4)	0.60 (2)
H15	0.8895	0.0548	0.1987	0.119*	0.60 (2)
C16	0.7852 (14)	0.1733 (16)	0.1943 (5)	0.093 (4)	0.60 (2)
C13'	0.77 (2)	0.17 (3)	0.280 (8)	0.08 (2)	0.40 (2)
C14'	0.8675 (17)	0.150 (2)	0.2597 (5)	0.090 (5)	0.40 (2)
H14'	0.9277	0.1201	0.2746	0.108*	0.40 (2)
C15'	0.8866 (16)	0.171 (2)	0.2187 (4)	0.101 (6)	0.40 (2)
H15'	0.9528	0.1466	0.2057	0.121*	0.40 (2)
C16'	0.804 (2)	0.231 (2)	0.1972 (7)	0.093 (7)	0.40 (2)
C17	0.7175 (3)	0.2566 (4)	0.21498 (12)	0.0983 (14)
C18	0.7029 (3)	0.2470 (4)	0.25621 (10)	0.0825 (11)
H18	0.6475	0.2867	0.2700	0.099*
C19	0.7006 (9)	0.2752 (16)	0.1463 (3)	0.106 (4)	0.60 (2)
H19A	0.6400	0.2516	0.1279	0.128*	0.60 (2)
H19B	0.7384	0.3362	0.1341	0.128*	0.60 (2)
C19'	0.7263 (14)	0.356 (2)	0.1554 (5)	0.106 (6)	0.40 (2)
H19C	0.7669	0.4236	0.1531	0.128*	0.40 (2)
H19D	0.6721	0.3497	0.1329	0.128*	0.40 (2)
C20	0.5440 (2)	0.0408 (3)	0.43233 (9)	0.0621 (8)
H20A	0.5367	0.1045	0.4488	0.075*
H20B	0.6172	0.0078	0.4393	0.075*
C21	0.4498 (2)	−0.0335 (2)	0.44382 (8)	0.0499 (7)
C22	0.3463 (2)	0.0101 (2)	0.44082 (9)	0.0559 (7)
H22	0.3315	0.0787	0.4316	0.067*
C23	0.2654 (2)	−0.0602 (2)	0.45320 (8)	0.0513 (7)
C24	0.2828 (2)	−0.1680 (2)	0.46835 (8)	0.0487 (7)
C25	0.3817 (2)	−0.2133 (2)	0.47131 (9)	0.0574 (8)
H25	0.3948	−0.2824	0.4804	0.069*
C26	0.4654 (2)	−0.1425 (2)	0.45883 (9)	0.0558 (8)
H26	0.5412	−0.1667	0.4601	0.067*
C27	0.1083 (3)	−0.1372 (3)	0.46922 (11)	0.0717 (9)
H27A	0.0632	−0.1212	0.4934	0.086*
H27B	0.0555	−0.1648	0.4488	0.086*

	U11	U22	U33	U12	U13	U23
N1	0.0434 (12)	0.0635 (15)	0.0478 (13)	−0.0051 (11)	0.0046 (10)	0.0013 (11)
N2	0.0473 (12)	0.0744 (17)	0.0464 (13)	0.0051 (11)	0.0106 (10)	−0.0002 (11)
O1	0.0632 (12)	0.0731 (15)	0.0681 (14)	0.0019 (11)	−0.0056 (10)	−0.0107 (11)
O2	0.0709 (13)	0.0721 (15)	0.0594 (13)	0.0163 (11)	−0.0148 (10)	0.0034 (11)
O3	0.082 (5)	0.177 (12)	0.051 (5)	0.026 (6)	−0.014 (4)	0.002 (5)
O4	0.086 (4)	0.186 (10)	0.061 (3)	0.029 (5)	0.013 (3)	0.001 (4)
O3'	0.087 (9)	0.178 (19)	0.059 (10)	0.017 (10)	−0.007 (7)	0.016 (9)
O4'	0.089 (6)	0.170 (14)	0.056 (5)	0.019 (8)	0.022 (4)	0.018 (7)
O5	0.0477 (11)	0.0909 (17)	0.0790 (16)	−0.0153 (11)	−0.0004 (10)	0.0278 (12)
O6	0.0392 (11)	0.0932 (18)	0.1048 (19)	0.0071 (11)	0.0014 (11)	0.0294 (14)
C1	0.0401 (13)	0.0655 (19)	0.0459 (15)	0.0011 (12)	0.0079 (11)	0.0053 (13)
C2	0.106 (3)	0.083 (3)	0.074 (2)	−0.003 (2)	0.025 (2)	−0.011 (2)
C3	0.078 (2)	0.084 (3)	0.082 (2)	−0.0179 (19)	0.0173 (19)	−0.016 (2)
C4	0.142 (9)	0.179 (11)	0.092 (7)	−0.063 (8)	0.002 (6)	−0.025 (7)
C4'	0.142 (10)	0.179 (12)	0.092 (7)	−0.063 (8)	0.002 (6)	−0.025 (7)
C5	0.0328 (12)	0.0638 (18)	0.0391 (14)	−0.0030 (12)	0.0048 (10)	0.0073 (12)
C6	0.0421 (13)	0.0663 (18)	0.0369 (13)	−0.0011 (13)	−0.0017 (11)	0.0014 (13)
C7	0.0412 (13)	0.0646 (19)	0.0416 (14)	0.0006 (13)	0.0015 (11)	0.0098 (13)
C8	0.0388 (13)	0.0606 (18)	0.0479 (15)	−0.0056 (12)	0.0043 (12)	0.0011 (13)
C9	0.0409 (13)	0.081 (2)	0.0454 (15)	−0.0108 (14)	−0.0040 (12)	−0.0026 (14)
C10	0.0322 (12)	0.076 (2)	0.0426 (15)	−0.0022 (12)	−0.0012 (11)	0.0099 (14)
C11	0.072 (2)	0.069 (2)	0.067 (2)	0.0129 (17)	−0.0043 (17)	0.0012 (17)
C12	0.0470 (16)	0.122 (3)	0.055 (2)	0.0127 (17)	0.0109 (15)	0.0133 (18)
C13	0.052 (9)	0.13 (3)	0.050 (15)	0.020 (14)	0.022 (9)	0.018 (14)
C14	0.063 (5)	0.137 (10)	0.071 (5)	0.021 (5)	0.023 (4)	0.012 (6)
C15	0.070 (5)	0.160 (11)	0.068 (5)	0.030 (6)	0.020 (4)	0.000 (6)
C16	0.065 (6)	0.159 (13)	0.054 (5)	0.015 (8)	0.021 (4)	0.007 (8)
C13'	0.06 (4)	0.13 (6)	0.06 (6)	0.02 (3)	0.01 (4)	0.01 (5)
C14'	0.062 (9)	0.144 (16)	0.063 (7)	0.033 (9)	0.014 (6)	0.011 (9)
C15'	0.075 (9)	0.162 (16)	0.067 (7)	0.026 (10)	0.020 (6)	0.012 (9)
C16'	0.071 (10)	0.16 (2)	0.051 (8)	0.022 (12)	0.020 (7)	0.019 (12)
C17	0.058 (2)	0.173 (4)	0.064 (2)	0.023 (2)	0.0014 (18)	0.030 (3)
C18	0.0564 (19)	0.136 (3)	0.055 (2)	0.022 (2)	0.0081 (16)	0.007 (2)
C19	0.084 (6)	0.175 (13)	0.060 (5)	0.021 (7)	0.007 (4)	0.015 (6)
C19'	0.084 (8)	0.175 (18)	0.060 (7)	0.021 (10)	0.007 (6)	0.015 (9)
C20	0.0460 (15)	0.087 (2)	0.0538 (17)	−0.0097 (14)	−0.0003 (13)	0.0143 (16)
C21	0.0422 (14)	0.0650 (19)	0.0426 (15)	−0.0049 (13)	0.0007 (11)	0.0061 (13)
C22	0.0508 (16)	0.0562 (18)	0.0608 (18)	−0.0002 (13)	−0.0001 (14)	0.0141 (14)
C23	0.0396 (14)	0.0665 (19)	0.0479 (16)	0.0013 (13)	−0.0008 (12)	0.0061 (13)
C24	0.0442 (14)	0.0637 (18)	0.0381 (14)	−0.0058 (13)	−0.0001 (11)	0.0066 (12)
C25	0.0535 (16)	0.0630 (19)	0.0558 (17)	0.0047 (14)	0.0033 (13)	0.0163 (14)
C26	0.0448 (14)	0.072 (2)	0.0512 (16)	0.0047 (13)	0.0032 (12)	0.0107 (14)
C27	0.0446 (16)	0.101 (3)	0.070 (2)	−0.0090 (17)	−0.0053 (15)	0.0166 (19)

N1—C1	1.435 (3)	C8—C9	1.363 (4)
N1—C20	1.458 (4)	C9—C10	1.497 (4)
N1—C3	1.542 (4)	C9—H9	0.9300
N2—C12	1.379 (4)	C10—H10	0.9300
N2—C1	1.467 (4)	C11—H11A	0.9700
N2—C2	1.541 (4)	C11—H11B	0.9700
O1—C11	1.395 (4)	C12—C13'	1.4 (3)
O1—C8	1.474 (4)	C12—C13	1.57 (17)
O2—C7	1.408 (3)	C12—H12A	0.9700
O2—C11	1.482 (4)	C12—H12B	0.9700
O3—C17	1.389 (17)	C13—C18	1.3 (2)
O3—C19	1.409 (17)	C13—C14	1.4 (3)
O4—C19	1.394 (13)	C14—C15	1.392 (14)
O4—C16	1.402 (18)	C14—H14	0.9300
O3'—C19'	1.40 (3)	C15—C16	1.277 (19)
O3'—C17	1.43 (3)	C15—H15	0.9300
O4'—C19'	1.407 (19)	C16—C17	1.474 (18)
O4'—C16'	1.41 (3)	C13'—C14'	1.4 (3)
O5—C24	1.325 (3)	C13'—C18	1.4 (4)
O5—C27	1.413 (4)	C14'—C15'	1.39 (2)
O6—C23	1.288 (3)	C14'—H14'	0.9300
O6—C27	1.486 (4)	C15'—C16'	1.41 (3)
C1—C5	1.628 (4)	C15'—H15'	0.9300
C1—H1	0.9800	C16'—C17	1.20 (2)
C2—C3	1.528 (5)	C17—C18	1.367 (5)
C2—C4	1.532 (11)	C18—H18	0.9300
C2—H2	0.9800	C19—H19A	0.9700
C2—H2A	0.9700	C19—H19B	0.9700
C2—H2B	0.9700	C19'—H19C	0.9700
C3—C4'	1.531 (12)	C19'—H19D	0.9700
C3—H3A	0.9700	C20—C21	1.485 (4)
C3—H3B	0.9700	C20—H20A	0.9700
C3—H3	0.9800	C20—H20B	0.9700
C4—H4A	0.9600	C21—C22	1.322 (4)
C4—H4B	0.9600	C21—C26	1.467 (4)
C4—H4C	0.9600	C22—C23	1.351 (4)
C4'—H4'1	0.9600	C22—H22	0.9300
C4'—H4'2	0.9600	C23—C24	1.458 (4)
C4'—H4'3	0.9600	C24—C25	1.284 (4)
C5—C10	1.385 (4)	C25—C26	1.379 (4)
C5—C6	1.400 (4)	C25—H25	0.9300
C6—C7	1.461 (4)	C26—H26	0.9300
C6—H6	0.9300	C27—H27A	0.9700
C7—C8	1.369 (4)	C27—H27B	0.9700
C1—N1—C20	112.2 (2)	N2—C12—H12B	108.6
C1—N1—C3	110.1 (2)	C13'—C12—H12B	113.0
C20—N1—C3	108.9 (3)	C13—C12—H12B	108.6
C12—N2—C1	111.3 (2)	H12A—C12—H12B	107.6
C12—N2—C2	113.3 (3)	C18—C13—C14	122 (10)
C1—N2—C2	106.1 (2)	C18—C13—C12	121 (10)
C11—O1—C8	105.0 (2)	C14—C13—C12	114 (10)
C7—O2—C11	110.7 (2)	C15—C14—C13	117 (8)
C17—O3—C19	108.5 (12)	C15—C14—H14	121.4
C19—O4—C16	107.3 (9)	C13—C14—H14	121.4
C19'—O3'—C17	110.1 (18)	C16—C15—C14	118.7 (11)
C19'—O4'—C16'	107.5 (13)	C16—C15—H15	120.6
C24—O5—C27	97.4 (2)	C14—C15—H15	120.6
C23—O6—C27	100.0 (2)	C15—C16—O4	128.5 (13)
N1—C1—N2	101.5 (2)	C15—C16—C17	123.9 (13)
N1—C1—C5	118.0 (2)	O4—C16—C17	107.5 (12)
N2—C1—C5	110.7 (2)	C14'—C13'—C12	123 (10)
N1—C1—H1	108.8	C14'—C13'—C18	107 (10)
N2—C1—H1	108.8	C12—C13'—C18	123 (10)
C5—C1—H1	108.8	C13'—C14'—C15'	125 (10)
C3—C2—C4	101.4 (5)	C13'—C14'—H14'	117.7
C3—C2—N2	105.8 (3)	C15'—C14'—H14'	117.7
C4—C2—N2	107.3 (6)	C14'—C15'—C16'	118.5 (14)
C3—C2—H2	113.8	C14'—C15'—H15'	120.7
C4—C2—H2	113.8	C16'—C15'—H15'	120.7
N2—C2—H2	113.8	C17—C16'—C15'	118.0 (19)
C3—C2—H2A	110.6	C17—C16'—O4'	111 (2)
N2—C2—H2A	110.6	C15'—C16'—O4'	130.9 (19)
H2—C2—H2A	102.5	C16'—C17—C18	124.0 (13)
C3—C2—H2B	110.6	C16'—C17—O3	102.3 (14)
C4—C2—H2B	120.0	C18—C17—O3	133.4 (7)
N2—C2—H2B	110.6	C16'—C17—O3'	106.3 (16)
H2A—C2—H2B	108.7	C18—C17—O3'	120.8 (10)
C2—C3—C4'	93.2 (5)	C18—C17—C16	117.3 (8)
C2—C3—N1	101.2 (3)	O3—C17—C16	104.9 (9)
C4'—C3—N1	105.0 (6)	O3'—C17—C16	121.9 (12)
C2—C3—H3A	111.5	C13—C18—C17	118 (8)
C4'—C3—H3A	129.8	C17—C18—C13'	122 (10)
N1—C3—H3A	111.5	C13—C18—H18	121.2
C2—C3—H3B	111.5	C17—C18—H18	121.2
N1—C3—H3B	111.5	C13'—C18—H18	118.0
H3A—C3—H3B	109.3	O4—C19—O3	109.0 (10)
C2—C3—H3	117.9	O4—C19—H19A	109.9
C4'—C3—H3	117.9	O3—C19—H19A	109.9
N1—C3—H3	117.9	O4—C19—H19B	109.9
C2—C4—H4A	109.5	O3—C19—H19B	109.9
C2—C4—H4B	109.5	H19A—C19—H19B	108.3
C2—C4—H4C	109.5	O3'—C19'—O4'	100.6 (15)
C3—C4'—H4'1	109.5	O3'—C19'—H19C	111.6
C3—C4'—H4'2	109.5	O4'—C19'—H19C	111.6
H4'1—C4'—H4'2	109.5	O3'—C19'—H19D	111.6
C3—C4'—H4'3	109.5	O4'—C19'—H19D	111.6
H4'1—C4'—H4'3	109.5	H19C—C19'—H19D	109.4
H4'2—C4'—H4'3	109.5	N1—C20—C21	115.9 (2)
C10—C5—C6	114.8 (3)	N1—C20—H20A	108.3
C10—C5—C1	122.3 (2)	C21—C20—H20A	108.3
C6—C5—C1	122.8 (2)	N1—C20—H20B	108.3
C5—C6—C7	120.4 (2)	C21—C20—H20B	108.3
C5—C6—H6	119.8	H20A—C20—H20B	107.4
C7—C6—H6	119.8	C22—C21—C26	121.6 (3)
C8—C7—O2	104.3 (2)	C22—C21—C20	112.8 (3)
C8—C7—C6	124.5 (2)	C26—C21—C20	125.5 (2)
O2—C7—C6	131.2 (2)	C21—C22—C23	109.6 (3)
C9—C8—C7	116.6 (3)	C21—C22—H22	125.2
C9—C8—O1	130.2 (3)	C23—C22—H22	125.2
C7—C8—O1	113.2 (2)	O6—C23—C22	121.5 (3)
C8—C9—C10	119.7 (2)	O6—C23—C24	110.5 (2)
C8—C9—H9	120.1	C22—C23—C24	128.0 (2)
C10—C9—H9	120.1	C25—C24—O5	120.8 (3)
C5—C10—C9	123.9 (2)	C25—C24—C23	124.1 (3)
C5—C10—H10	118.1	O5—C24—C23	115.1 (2)
C9—C10—H10	118.1	C24—C25—C26	108.6 (3)
O1—C11—O2	105.9 (2)	C24—C25—H25	125.7
O1—C11—H11A	110.5	C26—C25—H25	125.7
O2—C11—H11A	110.5	C25—C26—C21	128.0 (3)
O1—C11—H11B	110.5	C25—C26—H26	116.0
O2—C11—H11B	110.5	C21—C26—H26	116.0
H11A—C11—H11B	108.7	O5—C27—O6	116.9 (2)
N2—C12—C13'	111 (10)	O5—C27—H27A	108.1
N2—C12—C13	115 (7)	O6—C27—H27A	108.1
N2—C12—H12A	108.6	O5—C27—H27B	108.1
C13'—C12—H12A	106.0	O6—C27—H27B	108.1
C13—C12—H12A	108.6	H27A—C27—H27B	107.3