rac-(1R*,2S*,3S*)-Diethyl 4-methyl-2-phenyl-6-(2-phenyl­hydrazinyl­idene)cyclo­hex-4-ene-1,3-dicarboxyl­ate

Maharramov, A.M.; Ismiyev, A.I.; Rashidov, B.A.

doi:10.1107/S1600536810045058

organic compounds

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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page o153

https://doi.org/10.1107/S1600536810045058

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rac-(1R,2S,3S*)-Diethyl 4-methyl-2-phenyl-6-(2-phenylhydrazinylidene)cyclohex-4-ene-1,3-dicarboxylate

Abel M. Maharramov,^a Arif I. Ismiyev ^a and Bahruz A. Rashidov ^a ^*

^aBaku State University, Z. Khalilov St. 23, Baku, AZ-1148, Azerbaijan
^*Correspondence e-mail: Bahruz_81@mail.ru

(Received 1 July 2010; accepted 3 November 2010; online 18 December 2010)

In the title compound, C₂₅H₂₈N₂O₄, the cyclohexene ring adopts a half-chair conformation and the dihedral angle between the aromatic rings is 59.44 (11)°. In the crystal, a weak intermolecular N—H⋯O hydrogen bond occurs.

Related literature

For general background to Schiff bases, see: Cimerman et al. (1997 ); Offe et al. (1952 ); Richardson et al. (1988 ). For a related structure, see: Tamboura et al. (2009 ).

Experimental

Crystal data

C₂₅H₂₈N₂O₄
M_r = 420.49
Monoclinic, P 2₁ /c
a = 11.5271 (10) Å
b = 13.4599 (12) Å
c = 14.4479 (13) Å
β = 93.342 (2)°
V = 2237.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.30 × 0.30 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ) T_min = 0.975, T_max = 0.983
25227 measured reflections
5548 independent reflections
4052 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.149
S = 1.00
5548 reflections
289 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT-Plus (Bruker, 2001 ); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810045058/zb2008sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810045058/zb2008Isup2.hkl

checkCIF report

Comment top

Schiff bases have attracted much attention due to the possibility of their analytical applications (Cimerman et al., 1997). They are also important ligands, which have been reported to have mild bacteriostatic activity and as potential oral iron-chelating drugs for genetic disorders such as thalassemia (Offe et al., 1952; Richardson et al., 1988). Metal complexes based on Schiff bases have received considerable attention because they can be utilized as model compounds of active centres in various complexes (Tamboura et al., 2009). (rac)-Diethyl-4-methyl-2-phenyl-6-(2-phenylhydrazono)cyclohex-4-ene-1,3-dicarboxylate (I) have good antibacterial properties. We have synthesized the title compound, (I), and its structure is reported here (Fig. 1)..

Related literature top

For general background to Schiff bases, see: Cimerman et al. (1997); Offe et al. (1952); Richardson et al. (1988). For a related structure, see: Tamboura et al. (2009).

Experimental top

(rac)-diethyl-4-hydroxy-4-methyl-6-oxo-2-phenyl-1,3-dicarboxylate (20 mmol), phenylhydrazine (20 mmol) were dissolved in 20 ml ethanol. The mixture was stirred at 345–350 K for 10 h. After cooling to room temperature white crystals were obtained. The crystals was filtered and washed with ethanol. recrystallization from ethanol (50 ml) yielded colourless block-shaped crystals of the title compound.

Structure description top

For general background to Schiff bases, see: Cimerman et al. (1997); Offe et al. (1952); Richardson et al. (1988). For a related structure, see: Tamboura et al. (2009).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, with the atomic numberingscheme. Displacement ellipsoids were drawn at the 50% probability level.

rac-(1R*,2S*,3S*)-Diethyl 4-methyl-2-phenyl-6-(2-phenylhydrazinylidene)cyclohex-4-ene-1,3-dicarboxylate top

Crystal data top

C₂₅H₂₈N₂O₄	F(000) = 896
M_r = 420.49	D_x = 1.248 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 444 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.5271 (10) Å	Cell parameters from 8834 reflections
b = 13.4599 (12) Å	θ = 2.2–28.2°
c = 14.4479 (13) Å	µ = 0.09 mm⁻¹
β = 93.342 (2)°	T = 296 K
V = 2237.8 (3) Å³	Block, colourless
Z = 4	0.30 × 0.30 × 0.20 mm

Data collection top

Bruker APEXII CCD diffractometer	5548 independent reflections
Radiation source: fine-focus sealed tube	4052 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
φ and ω scans	θ_max = 28.3°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −15→15
T_min = 0.975, T_max = 0.983	k = −17→17
25227 measured reflections	l = −19→19

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)] = 0.051	Hydrogen site location: difference Fourier map
wR(F²) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0638P)² + 0.859P] where P = (F_o² + 2F_c²)/3
5548 reflections	(Δ/σ)_max = 0.004
289 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₅H₂₈N₂O₄	V = 2237.8 (3) Å³
M_r = 420.49	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.5271 (10) Å	µ = 0.09 mm⁻¹
b = 13.4599 (12) Å	T = 296 K
c = 14.4479 (13) Å	0.30 × 0.30 × 0.20 mm
β = 93.342 (2)°

Data collection top

Bruker APEXII CCD diffractometer	5548 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	4052 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.983	R_int = 0.022
25227 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.34 e Å⁻³
5548 reflections	Δρ_min = −0.24 e Å⁻³
289 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
O1	0.15913 (9)	0.34836 (9)	0.54219 (8)	0.0484 (3)
O2	0.17111 (13)	0.50496 (11)	0.59085 (11)	0.0709 (4)
N1	0.30804 (12)	0.45097 (10)	0.40168 (8)	0.0419 (3)
C1	0.34611 (13)	0.41600 (11)	0.56061 (9)	0.0380 (3)
H1B	0.3852	0.4757	0.5855	0.046*
C2	0.38941 (12)	0.32697 (11)	0.61990 (9)	0.0361 (3)
H2A	0.3507	0.2673	0.5944	0.043*
C3	0.52040 (13)	0.31464 (12)	0.60926 (10)	0.0413 (3)
H3A	0.5596	0.3754	0.6316	0.050*
C4	0.54451 (14)	0.30086 (16)	0.50773 (12)	0.0542 (4)
C5	0.47578 (14)	0.34400 (14)	0.44177 (11)	0.0490 (4)
H5A	0.4929	0.3345	0.3803	0.059*
C6	0.37661 (13)	0.40445 (11)	0.46046 (10)	0.0382 (3)
C7	0.23724 (14)	0.47893 (11)	0.24792 (10)	0.0428 (3)
N2	0.32965 (12)	0.45154 (10)	0.30993 (8)	0.0448 (3)
H2B	0.3966	0.4359	0.2911	0.054*
O3	0.67654 (10)	0.24545 (9)	0.69781 (9)	0.0594 (3)
O4	0.51562 (11)	0.15407 (9)	0.68262 (10)	0.0594 (3)
C8	0.25723 (17)	0.48808 (14)	0.15465 (11)	0.0531 (4)
H8A	0.3309	0.4760	0.1341	0.064*
C9	0.16733 (19)	0.51528 (16)	0.09237 (12)	0.0627 (5)
H9A	0.1813	0.5221	0.0299	0.075*
C10	0.05779 (19)	0.53242 (15)	0.12122 (13)	0.0646 (5)
H10A	−0.0021	0.5506	0.0787	0.078*
C11	0.03751 (18)	0.52248 (17)	0.21352 (14)	0.0658 (5)
H11A	−0.0366	0.5339	0.2334	0.079*
C12	0.12618 (16)	0.49575 (15)	0.27715 (12)	0.0565 (4)
H12A	0.1115	0.4890	0.3395	0.068*
C13	0.21677 (14)	0.43063 (12)	0.56620 (10)	0.0431 (3)
C14	0.03416 (16)	0.34864 (19)	0.54926 (17)	0.0726 (6)
H14A	−0.0022	0.3925	0.5029	0.087*
H14B	0.0150	0.3720	0.6100	0.087*
C15	−0.0078 (2)	0.2468 (3)	0.5345 (3)	0.0940 (9)
H15A	−0.089 (3)	0.246 (3)	0.543 (2)	0.141*
H15B	0.038 (3)	0.204 (3)	0.579 (2)	0.141*
H15C	0.010 (3)	0.229 (3)	0.464 (3)	0.141*
C16	0.35616 (14)	0.33795 (11)	0.71930 (10)	0.0418 (3)
C17	0.26498 (15)	0.28237 (14)	0.75034 (12)	0.0519 (4)
H17A	0.2261	0.2380	0.7101	0.062*
C18	0.2309 (2)	0.29172 (18)	0.83973 (15)	0.0698 (6)
H18A	0.1696	0.2537	0.8593	0.084*
C19	0.2866 (3)	0.35647 (19)	0.89953 (15)	0.0816 (7)
H19A	0.2641	0.3621	0.9601	0.098*
C20	0.3760 (3)	0.41330 (18)	0.87026 (14)	0.0831 (7)
H20A	0.4133	0.4583	0.9108	0.100*
C21	0.4114 (2)	0.40414 (15)	0.78021 (12)	0.0633 (5)
H21A	0.4724	0.4427	0.7609	0.076*
C22	0.56773 (13)	0.22838 (12)	0.66713 (11)	0.0430 (3)
C23	0.73944 (16)	0.16560 (15)	0.74630 (14)	0.0617 (5)
H23A	0.7502	0.1102	0.7047	0.074*
H23B	0.6968	0.1424	0.7980	0.074*
C24	0.85377 (18)	0.2070 (2)	0.78001 (17)	0.0780 (7)
H24A	0.8982	0.1564	0.8127	0.117*
H24B	0.8418	0.2618	0.8209	0.117*
H24C	0.8951	0.2295	0.7282	0.117*
C25	0.6461 (2)	0.2380 (3)	0.48389 (17)	0.1185 (13)
H25A	0.6504	0.2357	0.4178	0.178*
H25B	0.6363	0.1719	0.5072	0.178*
H25C	0.7164	0.2661	0.5115	0.178*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0358 (6)	0.0533 (7)	0.0561 (7)	0.0049 (5)	0.0021 (5)	−0.0080 (5)
O2	0.0700 (9)	0.0599 (8)	0.0818 (10)	0.0231 (7)	−0.0039 (7)	−0.0232 (7)
N1	0.0497 (7)	0.0413 (7)	0.0344 (6)	0.0034 (6)	−0.0012 (5)	0.0019 (5)
C1	0.0425 (8)	0.0365 (7)	0.0343 (7)	−0.0010 (6)	−0.0029 (6)	0.0003 (5)
C2	0.0357 (7)	0.0364 (7)	0.0360 (7)	−0.0020 (6)	0.0000 (5)	0.0017 (5)
C3	0.0348 (7)	0.0452 (8)	0.0433 (8)	−0.0026 (6)	−0.0031 (6)	0.0091 (6)
C4	0.0373 (8)	0.0774 (12)	0.0486 (9)	0.0092 (8)	0.0081 (7)	0.0155 (8)
C5	0.0427 (8)	0.0659 (11)	0.0389 (8)	0.0058 (7)	0.0065 (6)	0.0091 (7)
C6	0.0397 (7)	0.0394 (7)	0.0352 (7)	−0.0023 (6)	−0.0009 (6)	0.0024 (6)
C7	0.0527 (9)	0.0384 (7)	0.0367 (7)	0.0047 (6)	−0.0036 (6)	0.0012 (6)
N2	0.0461 (7)	0.0538 (8)	0.0342 (6)	0.0071 (6)	0.0004 (5)	0.0036 (5)
O3	0.0478 (7)	0.0564 (7)	0.0712 (8)	−0.0034 (5)	−0.0201 (6)	0.0201 (6)
O4	0.0492 (7)	0.0458 (7)	0.0826 (9)	−0.0026 (5)	0.0003 (6)	0.0151 (6)
C8	0.0588 (10)	0.0610 (10)	0.0392 (8)	0.0037 (8)	0.0005 (7)	0.0032 (7)
C9	0.0834 (14)	0.0677 (12)	0.0356 (8)	0.0030 (10)	−0.0093 (8)	0.0033 (8)
C10	0.0725 (13)	0.0640 (12)	0.0546 (11)	0.0151 (10)	−0.0213 (9)	−0.0022 (9)
C11	0.0568 (11)	0.0783 (13)	0.0610 (11)	0.0204 (10)	−0.0070 (9)	−0.0033 (10)
C12	0.0607 (11)	0.0679 (11)	0.0407 (8)	0.0168 (9)	0.0014 (7)	0.0012 (8)
C13	0.0485 (9)	0.0461 (8)	0.0343 (7)	0.0090 (7)	−0.0021 (6)	−0.0034 (6)
C14	0.0381 (9)	0.0907 (16)	0.0884 (15)	0.0118 (10)	−0.0004 (9)	−0.0160 (12)
C15	0.0479 (12)	0.112 (2)	0.122 (2)	−0.0180 (13)	0.0054 (13)	−0.0147 (18)
C16	0.0499 (9)	0.0390 (7)	0.0365 (7)	0.0062 (6)	0.0025 (6)	0.0059 (6)
C17	0.0531 (10)	0.0524 (9)	0.0511 (9)	0.0061 (8)	0.0100 (7)	0.0106 (7)
C18	0.0753 (13)	0.0769 (14)	0.0599 (12)	0.0185 (11)	0.0279 (10)	0.0203 (11)
C19	0.123 (2)	0.0778 (15)	0.0462 (11)	0.0353 (15)	0.0256 (12)	0.0136 (10)
C20	0.138 (2)	0.0670 (13)	0.0436 (10)	0.0085 (14)	−0.0038 (12)	−0.0099 (9)
C21	0.0915 (15)	0.0558 (11)	0.0421 (9)	−0.0110 (10)	−0.0010 (9)	−0.0008 (8)
C22	0.0402 (8)	0.0459 (8)	0.0427 (8)	−0.0002 (6)	−0.0003 (6)	0.0056 (6)
C23	0.0590 (11)	0.0592 (11)	0.0649 (11)	0.0090 (9)	−0.0131 (9)	0.0151 (9)
C24	0.0550 (12)	0.0930 (17)	0.0841 (15)	0.0032 (11)	−0.0133 (10)	0.0266 (13)
C25	0.0849 (17)	0.206 (4)	0.0673 (14)	0.085 (2)	0.0294 (13)	0.0412 (18)

Geometric parameters (Å, º) top

O1—C13	1.327 (2)	C10—H10A	0.9300
O1—C14	1.450 (2)	C11—C12	1.382 (3)
O2—C13	1.1944 (19)	C11—H11A	0.9300
N1—C6	1.2884 (19)	C12—H12A	0.9300
N1—N2	1.3630 (17)	C14—C15	1.465 (4)
C1—C13	1.511 (2)	C14—H14A	0.9700
C1—C6	1.5169 (19)	C14—H14B	0.9700
C1—C2	1.5392 (19)	C15—H15A	0.95 (4)
C1—H1B	0.9800	C15—H15B	0.99 (4)
C2—C16	1.515 (2)	C15—H15C	1.08 (4)
C2—C3	1.536 (2)	C16—C21	1.381 (2)
C2—H2A	0.9800	C16—C17	1.386 (2)
C3—C22	1.514 (2)	C17—C18	1.377 (3)
C3—C4	1.520 (2)	C17—H17A	0.9300
C3—H3A	0.9800	C18—C19	1.362 (4)
C4—C5	1.336 (2)	C18—H18A	0.9300
C4—C25	1.501 (3)	C19—C20	1.370 (4)
C5—C6	1.441 (2)	C19—H19A	0.9300
C5—H5A	0.9300	C20—C21	1.391 (3)
C7—C8	1.386 (2)	C20—H20A	0.9300
C7—C12	1.390 (2)	C21—H21A	0.9300
C7—N2	1.401 (2)	C23—C24	1.486 (3)
N2—H2B	0.8600	C23—H23A	0.9700
O3—C22	1.3257 (19)	C23—H23B	0.9700
O3—C23	1.453 (2)	C24—H24A	0.9600
O4—C22	1.1945 (19)	C24—H24B	0.9600
C8—C9	1.382 (3)	C24—H24C	0.9600
C8—H8A	0.9300	C25—H25A	0.9600
C9—C10	1.372 (3)	C25—H25B	0.9600
C9—H9A	0.9300	C25—H25C	0.9600
C10—C11	1.374 (3)

C13—O1—C14	117.62 (14)	O1—C13—C1	110.96 (12)
C6—N1—N2	120.26 (13)	O1—C14—C15	107.96 (18)
C13—C1—C6	110.41 (11)	O1—C14—H14A	110.1
C13—C1—C2	111.15 (12)	C15—C14—H14A	110.1
C6—C1—C2	111.43 (12)	O1—C14—H14B	110.1
C13—C1—H1B	107.9	C15—C14—H14B	110.1
C6—C1—H1B	107.9	H14A—C14—H14B	108.4
C2—C1—H1B	107.9	C14—C15—H15A	108 (2)
C16—C2—C3	114.21 (12)	C14—C15—H15B	107 (2)
C16—C2—C1	111.09 (12)	H15A—C15—H15B	113 (3)
C3—C2—C1	108.50 (11)	C14—C15—H15C	106 (2)
C16—C2—H2A	107.6	H15A—C15—H15C	111 (3)
C3—C2—H2A	107.6	H15B—C15—H15C	111 (3)
C1—C2—H2A	107.6	C21—C16—C17	118.16 (16)
C22—C3—C4	111.04 (14)	C21—C16—C2	122.30 (15)
C22—C3—C2	110.64 (12)	C17—C16—C2	119.51 (14)
C4—C3—C2	110.24 (12)	C18—C17—C16	121.14 (19)
C22—C3—H3A	108.3	C18—C17—H17A	119.4
C4—C3—H3A	108.3	C16—C17—H17A	119.4
C2—C3—H3A	108.3	C19—C18—C17	120.3 (2)
C5—C4—C25	121.29 (17)	C19—C18—H18A	119.9
C5—C4—C3	120.07 (15)	C17—C18—H18A	119.9
C25—C4—C3	118.63 (15)	C18—C19—C20	119.80 (19)
C4—C5—C6	123.75 (15)	C18—C19—H19A	120.1
C4—C5—H5A	118.1	C20—C19—H19A	120.1
C6—C5—H5A	118.1	C19—C20—C21	120.4 (2)
N1—C6—C5	127.86 (14)	C19—C20—H20A	119.8
N1—C6—C1	114.30 (13)	C21—C20—H20A	119.8
C5—C6—C1	117.84 (12)	C16—C21—C20	120.3 (2)
C8—C7—C12	119.29 (15)	C16—C21—H21A	119.9
C8—C7—N2	118.82 (15)	C20—C21—H21A	119.9
C12—C7—N2	121.88 (14)	O4—C22—O3	123.97 (15)
N1—N2—C7	116.63 (13)	O4—C22—C3	125.21 (14)
N1—N2—H2B	121.7	O3—C22—C3	110.81 (13)
C7—N2—H2B	121.7	O3—C23—C24	106.77 (16)
C22—O3—C23	117.95 (14)	O3—C23—H23A	110.4
C9—C8—C7	119.73 (17)	C24—C23—H23A	110.4
C9—C8—H8A	120.1	O3—C23—H23B	110.4
C7—C8—H8A	120.1	C24—C23—H23B	110.4
C10—C9—C8	121.02 (17)	H23A—C23—H23B	108.6
C10—C9—H9A	119.5	C23—C24—H24A	109.5
C8—C9—H9A	119.5	C23—C24—H24B	109.5
C9—C10—C11	119.35 (17)	H24A—C24—H24B	109.5
C9—C10—H10A	120.3	C23—C24—H24C	109.5
C11—C10—H10A	120.3	H24A—C24—H24C	109.5
C10—C11—C12	120.66 (19)	H24B—C24—H24C	109.5
C10—C11—H11A	119.7	C4—C25—H25A	109.5
C12—C11—H11A	119.7	C4—C25—H25B	109.5
C11—C12—C7	119.93 (17)	H25A—C25—H25B	109.5
C11—C12—H12A	120.0	C4—C25—H25C	109.5
C7—C12—H12A	120.0	H25A—C25—H25C	109.5
O2—C13—O1	123.66 (16)	H25B—C25—H25C	109.5
O2—C13—C1	125.35 (16)

C13—C1—C2—C16	−55.07 (15)	C10—C11—C12—C7	0.2 (3)
C6—C1—C2—C16	−178.68 (12)	C8—C7—C12—C11	−0.8 (3)
C13—C1—C2—C3	178.60 (12)	N2—C7—C12—C11	−179.88 (18)
C6—C1—C2—C3	54.99 (15)	C14—O1—C13—O2	−1.9 (2)
C16—C2—C3—C22	54.95 (17)	C14—O1—C13—C1	176.44 (15)
C1—C2—C3—C22	179.45 (12)	C6—C1—C13—O2	−113.05 (18)
C16—C2—C3—C4	178.17 (13)	C2—C1—C13—O2	122.76 (18)
C1—C2—C3—C4	−57.33 (16)	C6—C1—C13—O1	68.60 (16)
C22—C3—C4—C5	154.18 (17)	C2—C1—C13—O1	−55.59 (16)
C2—C3—C4—C5	31.2 (2)	C13—O1—C14—C15	−170.7 (2)
C22—C3—C4—C25	−25.6 (3)	C3—C2—C16—C21	49.1 (2)
C2—C3—C4—C25	−148.6 (2)	C1—C2—C16—C21	−74.00 (19)
C25—C4—C5—C6	179.5 (2)	C3—C2—C16—C17	−132.94 (15)
C3—C4—C5—C6	−0.3 (3)	C1—C2—C16—C17	103.95 (16)
N2—N1—C6—C5	−4.2 (2)	C21—C16—C17—C18	−0.8 (3)
N2—N1—C6—C1	176.16 (12)	C2—C16—C17—C18	−178.81 (16)
C4—C5—C6—N1	177.79 (18)	C16—C17—C18—C19	0.1 (3)
C4—C5—C6—C1	−2.6 (3)	C17—C18—C19—C20	0.7 (3)
C13—C1—C6—N1	29.81 (18)	C18—C19—C20—C21	−1.0 (4)
C2—C1—C6—N1	153.84 (13)	C17—C16—C21—C20	0.5 (3)
C13—C1—C6—C5	−149.86 (14)	C2—C16—C21—C20	178.51 (18)
C2—C1—C6—C5	−25.83 (18)	C19—C20—C21—C16	0.3 (3)
C6—N1—N2—C7	162.94 (14)	C23—O3—C22—O4	5.6 (3)
C8—C7—N2—N1	175.09 (14)	C23—O3—C22—C3	−173.54 (15)
C12—C7—N2—N1	−5.8 (2)	C4—C3—C22—O4	−89.5 (2)
C12—C7—C8—C9	1.1 (3)	C2—C3—C22—O4	33.2 (2)
N2—C7—C8—C9	−179.83 (17)	C4—C3—C22—O3	89.58 (17)
C7—C8—C9—C10	−0.7 (3)	C2—C3—C22—O3	−147.67 (14)
C8—C9—C10—C11	0.1 (3)	C22—O3—C23—C24	−175.08 (17)
C9—C10—C11—C12	0.2 (3)

Experimental details

Crystal data
Chemical formula	C₂₅H₂₈N₂O₄
M_r	420.49
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	11.5271 (10), 13.4599 (12), 14.4479 (13)
β (°)	93.342 (2)
V (Å³)	2237.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.30 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1998)
T_min, T_max	0.975, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	25227, 5548, 4052
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.149, 1.00
No. of reflections	5548
No. of parameters	289
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.24

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2001), SHELXTL (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Acknowledgements

We thank Professor Victor N. Khrustalev for fruitful discussions and help with this work.

References

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