4-Methyl-1,3-bis­(3,4-methyl­enedioxy­benz­yl)-2-(3,4-methyl­enedioxy­phen­yl)imidazolidine

Yang, S.-P.; Han, L.-J.; Wen, A.-P.; Wang, D.-Q.

doi:10.1107/S1600536809046662

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3049

doi:10.1107/S1600536809046662

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4-Methyl-1,3-bis(3,4-methylenedioxybenzyl)-2-(3,4-methylenedioxyphenyl)imidazolidine

Shu-Ping Yang,^a ^* Li-Jun Han,^b Ai-Ping Wen ^c and Da-Qi Wang ^d

^aSchool of Chemical Engineering, Huaihai Institute of Technology, Lianyungang 222005, People's Republic of China, ^bSchool of Mathematics and Science, Huaihai Institute of Technology, Lianyungang 222005, People's Republic of China, ^cSchool of Pharmacy, Inner Mongolia Medical College, Hohhot 010059, People's Republic of China, and ^dCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: spyang69320@yahoo.cn

(Received 15 October 2009; accepted 5 November 2009; online 11 November 2009)

In the title compound, C₂₇H₂₆N₂O₆, 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-methylenedioxyphenyl 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_r = 474.50
Orthorhombic, P b c n
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[F² > 2σ(F²)] = 0.066
wR(F²) = 0.215
S = 1.07
4200 reflections
392 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −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.

Supporting information

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

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

checkCIF report

Comment top

Some imidazolidine derivatives exhibit a broad spectrum of biological activities (Sasho et al., 1994). The crystal structures of some imidazolidine compounds have reported (Xia et al., 2007; Iskenderov et al., 2009). Here, we report the crystal structure of a new imidazolidine compound (I).

In the title compound (I) (Fig.1), the imidazolidine ring adopts an envelope conformation. The methyl on the imidazolidine ring is disordered over two positions, leading to positional disorder of the two methylene H atoms of the ring, with occupancies of 0.517 (11) and 0.483 (11).

The 3, 4-methylenedioxyphenyl at the 3-position on imidazolidine ring is disordered over two positions, with occupancies of 0.60 (2) and 0.40 (2). The dihedral angles between the planes of the two disordered benzyl rings C13—C18 and C13'-C16'/C17/C18 is 26 (7)°, and the planes of the two disordered methylenedioxy rings C17/O3/C19/O4/C16 and C17/O3'/C19'/O4'/C16' are 21 (1)°.

In the imidazolidine ring, the C—N bond lengths range from 1.435 (4) to 1.542 (4) Å, which are close the average single C—N bond lengths of 1.48 Å.

Related literature top

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

Experimental top

The reaction mixture containing 3,4-methylenedioxybenzaldehyde (3.0 g, 20 mmol) and propane-1,2-diamine (2.8 g, 20 mmol) was refluxed for about 4 h in ethanol (30 ml), then the borohydride sodium (1.52 g, 40 mmol) was added and stirred for 4 h (at 333–343 K), and the reaction mixture was cooled and the crude products were filtered off, washed with water and ethanol, then dried. Colourless crystals of (I) suitable for X-ray structure analysis were obtained by recrystallizing the crude product from ethanol (m.p. 478–480 K).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), showing the disorder components and the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

4-Methyl-1,3-bis(3,4-methylenedioxybenzyl)-2-(3,4- methylenedioxyphenyl)imidazolidine top

Crystal data top

C₂₇H₂₆N₂O₆	D_x = 1.321 Mg m⁻³
M_r = 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

Data collection top

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

Refinement top

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(F_o²) + (0.1256P)² + 1.4629P] where P = (F_o² + 2F_c²)/3
4200 reflections	(Δ/σ)_max < 0.001
392 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₂₇H₂₆N₂O₆	V = 4771.3 (17) Å³
M_r = 474.50	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 11.586 (2) Å	µ = 0.09 mm⁻¹
b = 12.575 (3) Å	T = 298 K
c = 32.749 (7) Å	0.50 × 0.40 × 0.30 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4200 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2896 reflections with I > 2σ(I)
T_min = 0.955, T_max = 0.972	R_int = 0.055
19793 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.215	H-atom parameters constrained
S = 1.07	Δρ_max = 0.40 e Å⁻³
4200 reflections	Δρ_min = −0.43 e Å⁻³
392 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₂₇H₂₆N₂O₆
M_r	474.50
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	298
a, b, c (Å)	11.586 (2), 12.575 (3), 32.749 (7)
V (Å³)	4771.3 (17)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.50 × 0.40 × 0.30

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.955, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	19793, 4200, 2896
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.215, 1.07
No. of reflections	4200
No. of parameters	392
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.43

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXTL (Sheldrick, 2008).

References

Iskenderov, T. S., Golenya, I. A., Gumienna-Kontecka, E., Fritsky, I. O. & Prisyazhnaya, E. V. (2009). Acta Cryst. E65, o2123–o2124. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sasho, S., Obase, H., Ichikawa, S., Yoshizaki, R., Ishii, A. & Shuto, K. (1994). Bioorg. Med. Chem. Lett. 4, 615–618. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen,Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Xia, H.-T., Liu, Y.-F., Wang, D.-Q. & Li, B. (2007). Acta Cryst. E63, o3666. Web of Science CSD CrossRef IUCr Journals Google Scholar

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