tert-Butyl 4-({[(E)-1,3-dimethyl-5-phen­oxy­pyrazol-4-yl]meth­yl}amino­oxymeth­yl)benzoate

Fu, N.; Zou, X.-M.; Lin, D.-Y.; Zhu, Y.-Q.; Yang, H.-Z.

doi:10.1107/S160053680705427X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o192

https://doi.org/10.1107/S160053680705427X

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tert-Butyl 4-({[(E)-1,3-dimethyl-5-phenoxypyrazol-4-yl]methyl}aminooxymethyl)benzoate

Na Fu,^a Xiao-Mao Zou,^a ^* Da-Yong Lin,^a You-Quan Zhu ^a and Hua-Zheng Yang ^a

^aState Key Laboratory and Institute of Element-Organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China
^*Correspondence e-mail: funa2008@mail.nankai.edu.cn

(Received 27 October 2007; accepted 30 October 2007; online 6 December 2007)

The title compound, C₂₄H₂₇N₃O₄, also known as fenpyroximate, is a commercial acaricide. The benzene ring of the phenoxy group is approximately perpendicular to the pyrazole ring with a dihedral angle of 84.37 (11)°. The dihedral angle between the phenoxy and the benzoate benzene rings is 48.83 (8)°.

Related literature

For background to the design of bioactive molecules, see: Lewis et al. (1991 ) and for a related structure, see: Zou et al. (2006 ).

Experimental

Crystal data

C₂₄H₂₇N₃O₄
M_r = 421.49
Triclinic, $[P \overline 1]$
a = 9.672 (3) Å
b = 9.908 (3) Å
c = 13.179 (3) Å
α = 72.487 (5)°
β = 71.614 (5)°
γ = 74.494 (4)°
V = 1122.0 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 294 (2) K
0.32 × 0.24 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ) T_min = 0.972, T_max = 0.983
5754 measured reflections
3941 independent reflections
2284 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.175
S = 1.06
3941 reflections
284 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053680705427X/sj2396sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680705427X/sj2396Isup2.hkl

checkCIF report

Comment top

Since biological activities are related to the conformation of molecules, study of the relationships between chemical structure and biological activity is important in the rational design of bioactive molecules (Lewis et al., 1991). The title compound, also known as Fenpyroximate, is a commercial acaricide. Details of its crystal structure may be helpful for the design of new acaricidal compounds and we report here the structure of the title compound (I), Fig. 1. In (I), the benzene ring (C1/C2/C3/C4/C5/C6) is approximately perpendicular to the pyrazole ring with a dihedral angle of 84.37 (11) ° between them. The dihedral angle between the benzoate benzene ring(C14/C15/C16/C17/C18/C19) and the pyrazole ring is 64.87 (11) °. This is different to the dihedral angle between the pyrimidine ring and the pyrazole ring in (E)-5(3,5-dimethylphenoxy)-1,3-dimethyl-1H-pyrazole-4-carbaldehyde O-(2-chloropyrimidin-4-yl)oxime (Zou et al., 2006).

Related literature top

For background to the design of bioactive molecules, see: Lewis et al. (1991) and for a related structure, see: Zou et al. (2006).

Experimental top

Tert-butyl-(4-bromomethyl)benzoate(2.2 mmol), anhydrous potassium carbonate (4 mmol), and 1,3-dimethyl-5-phenoxy-1H-pyrazole-4- carbaldehyde oxime (2 mmol) were mixed in acetonitrile (40 ml) and refluxed for 5 h. The solvent was then evaporated in vacuo. The residue was recrystallized from ethanol and single crystals of (I) suitable for X-ray analysis were grown from ethyl acetate and petroleum ether at room temperature.

Structure description top

For background to the design of bioactive molecules, see: Lewis et al. (1991) and for a related structure, see: Zou et al. (2006).

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL (Bruker, 1999).

Figures top

Fig. 1. View of the title compound with displacement ellipsoids drawn at the 30% probability level.

tert-Butyl 4-({[(E)-1,3-dimethyl-5-phenoxypyrazol-4-yl]methyl}aminooxymethyl)benzoate top

Crystal data top

C₂₄H₂₇N₃O₄	Z = 2
M_r = 421.49	F(000) = 448
Triclinic, P1	D_x = 1.248 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.672 (3) Å	Cell parameters from 1585 reflections
b = 9.908 (3) Å	θ = 2.2–22.6°
c = 13.179 (3) Å	µ = 0.09 mm⁻¹
α = 72.487 (5)°	T = 294 K
β = 71.614 (5)°	Prism, colorless
γ = 74.494 (4)°	0.32 × 0.24 × 0.20 mm
V = 1122.0 (6) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3941 independent reflections
Radiation source: fine-focus sealed tube	2284 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
φ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −11→11
T_min = 0.972, T_max = 0.983	k = −8→11
5754 measured reflections	l = −10→15

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.175	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0841P)² + 0.1856P] where P = (F_o² + 2F_c²)/3
3941 reflections	(Δ/σ)_max < 0.001
284 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₄H₂₇N₃O₄	γ = 74.494 (4)°
M_r = 421.49	V = 1122.0 (6) Å³
Triclinic, P1	Z = 2
a = 9.672 (3) Å	Mo Kα radiation
b = 9.908 (3) Å	µ = 0.09 mm⁻¹
c = 13.179 (3) Å	T = 294 K
α = 72.487 (5)°	0.32 × 0.24 × 0.20 mm
β = 71.614 (5)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3941 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	2284 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.983	R_int = 0.022
5754 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.175	H-atom parameters constrained
S = 1.06	Δρ_max = 0.36 e Å⁻³
3941 reflections	Δρ_min = −0.22 e Å⁻³
284 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	0.26628 (19)	1.1772 (2)	−0.00386 (14)	0.0554 (5)
O2	0.3962 (2)	0.6532 (2)	0.19530 (16)	0.0616 (6)
O3	1.0760 (3)	0.3688 (3)	0.34012 (19)	0.0934 (9)
O4	0.9545 (2)	0.2420 (2)	0.49895 (15)	0.0561 (5)
N1	0.3522 (3)	1.2674 (3)	0.1062 (2)	0.0559 (6)
N2	0.4285 (3)	1.2208 (3)	0.1845 (2)	0.0609 (7)
N3	0.4010 (3)	0.7806 (3)	0.2206 (2)	0.0542 (6)
C1	0.1138 (3)	1.1919 (3)	0.0179 (2)	0.0441 (7)
C2	0.0642 (3)	1.1915 (3)	−0.0686 (2)	0.0601 (8)
H2	0.1307	1.1812	−0.1356	0.072*
C3	−0.0863 (4)	1.2068 (4)	−0.0544 (3)	0.0743 (10)
H3	−0.1213	1.2064	−0.1124	0.089*
C4	−0.1839 (4)	1.2223 (3)	0.0431 (3)	0.0673 (9)
H4	−0.2850	1.2318	0.0520	0.081*
C5	−0.1329 (3)	1.2238 (3)	0.1279 (3)	0.0612 (8)
H5	−0.2000	1.2349	0.1945	0.073*
C6	0.0167 (3)	1.2090 (3)	0.1166 (2)	0.0545 (8)
H6	0.0510	1.2106	0.1746	0.065*
C7	0.3276 (3)	1.1573 (3)	0.0806 (2)	0.0479 (7)
C8	0.3863 (3)	1.0308 (3)	0.1450 (2)	0.0456 (7)
C9	0.4502 (3)	1.0776 (3)	0.2080 (2)	0.0519 (7)
C10	0.5368 (4)	0.9888 (4)	0.2888 (3)	0.0734 (10)
H10A	0.5743	1.0507	0.3132	0.110*
H10B	0.6183	0.9235	0.2545	0.110*
H10C	0.4738	0.9348	0.3507	0.110*
C11	0.3029 (4)	1.4211 (3)	0.0637 (3)	0.0784 (10)
H11A	0.3730	1.4549	−0.0036	0.118*
H11B	0.2959	1.4727	0.1168	0.118*
H11C	0.2074	1.4370	0.0499	0.118*
C12	0.3833 (3)	0.8883 (3)	0.1411 (2)	0.0493 (7)
H12	0.3681	0.8747	0.0790	0.059*
C13	0.3981 (3)	0.5385 (3)	0.2913 (3)	0.0615 (8)
H13A	0.3680	0.4583	0.2816	0.074*
H13B	0.3258	0.5706	0.3536	0.074*
C14	0.5472 (3)	0.4862 (3)	0.3174 (2)	0.0499 (7)
C15	0.5588 (3)	0.3798 (3)	0.4126 (3)	0.0631 (9)
H15	0.4754	0.3429	0.4580	0.076*
C16	0.6917 (3)	0.3281 (3)	0.4406 (2)	0.0569 (8)
H16	0.6969	0.2582	0.5055	0.068*
C17	0.8173 (3)	0.3792 (3)	0.3734 (2)	0.0457 (7)
C18	0.8060 (3)	0.4847 (3)	0.2779 (2)	0.0536 (7)
H18	0.8900	0.5200	0.2315	0.064*
C19	0.6725 (3)	0.5377 (3)	0.2510 (2)	0.0518 (7)
H19	0.6667	0.6093	0.1872	0.062*
C20	0.9636 (3)	0.3290 (3)	0.4004 (2)	0.0532 (7)
C21	1.0809 (3)	0.1863 (3)	0.5491 (2)	0.0522 (7)
C22	1.2093 (4)	0.1033 (5)	0.4795 (3)	0.1094 (16)
H22A	1.1775	0.0273	0.4668	0.164*
H22B	1.2871	0.0626	0.5167	0.164*
H22C	1.2456	0.1668	0.4103	0.164*
C23	1.0184 (5)	0.0865 (5)	0.6550 (3)	0.1151 (17)
H23A	0.9339	0.1395	0.6979	0.173*
H23B	1.0927	0.0446	0.6955	0.173*
H23C	0.9886	0.0115	0.6394	0.173*
C24	1.1218 (5)	0.3089 (4)	0.5687 (4)	0.1043 (14)
H24A	1.1617	0.3702	0.4994	0.156*
H24B	1.1949	0.2726	0.6104	0.156*
H24C	1.0352	0.3630	0.6090	0.156*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0442 (11)	0.0691 (14)	0.0429 (11)	−0.0020 (9)	−0.0124 (9)	−0.0054 (9)
O2	0.0750 (14)	0.0483 (12)	0.0716 (14)	−0.0077 (10)	−0.0418 (11)	−0.0080 (10)
O3	0.0540 (14)	0.124 (2)	0.0669 (16)	−0.0101 (14)	−0.0133 (12)	0.0198 (14)
O4	0.0515 (12)	0.0629 (13)	0.0494 (12)	−0.0120 (9)	−0.0224 (9)	0.0041 (10)
N1	0.0533 (15)	0.0509 (15)	0.0583 (15)	−0.0045 (12)	−0.0181 (12)	−0.0063 (12)
N2	0.0529 (15)	0.0655 (18)	0.0656 (17)	−0.0076 (12)	−0.0213 (13)	−0.0145 (13)
N3	0.0561 (15)	0.0490 (15)	0.0595 (16)	−0.0021 (11)	−0.0254 (12)	−0.0114 (12)
C1	0.0431 (16)	0.0375 (15)	0.0456 (16)	−0.0048 (11)	−0.0137 (13)	−0.0010 (12)
C2	0.0605 (19)	0.071 (2)	0.0476 (18)	−0.0151 (16)	−0.0105 (15)	−0.0140 (15)
C3	0.068 (2)	0.094 (3)	0.071 (2)	−0.0225 (19)	−0.0294 (19)	−0.016 (2)
C4	0.0504 (19)	0.066 (2)	0.088 (3)	−0.0082 (15)	−0.0240 (19)	−0.0171 (18)
C5	0.0486 (18)	0.065 (2)	0.065 (2)	−0.0076 (15)	−0.0050 (15)	−0.0201 (16)
C6	0.0529 (18)	0.0619 (19)	0.0471 (18)	−0.0077 (14)	−0.0146 (14)	−0.0117 (14)
C7	0.0377 (15)	0.0532 (18)	0.0447 (16)	−0.0033 (13)	−0.0087 (13)	−0.0065 (13)
C8	0.0363 (14)	0.0491 (17)	0.0457 (16)	−0.0042 (12)	−0.0104 (12)	−0.0065 (13)
C9	0.0362 (15)	0.061 (2)	0.0538 (18)	−0.0045 (13)	−0.0124 (13)	−0.0102 (14)
C10	0.0582 (19)	0.084 (2)	0.081 (2)	−0.0019 (17)	−0.0388 (17)	−0.0120 (18)
C11	0.091 (3)	0.051 (2)	0.087 (3)	−0.0066 (17)	−0.030 (2)	−0.0051 (17)
C12	0.0393 (15)	0.0579 (19)	0.0472 (17)	−0.0026 (13)	−0.0161 (13)	−0.0079 (14)
C13	0.067 (2)	0.0487 (18)	0.074 (2)	−0.0127 (15)	−0.0381 (17)	0.0007 (15)
C14	0.0603 (18)	0.0389 (15)	0.0568 (18)	−0.0069 (13)	−0.0279 (15)	−0.0091 (13)
C15	0.0567 (19)	0.0589 (19)	0.067 (2)	−0.0178 (15)	−0.0245 (16)	0.0097 (15)
C16	0.0611 (19)	0.0506 (18)	0.0541 (18)	−0.0128 (14)	−0.0244 (15)	0.0067 (14)
C17	0.0513 (17)	0.0414 (15)	0.0439 (16)	−0.0029 (12)	−0.0165 (13)	−0.0102 (12)
C18	0.0520 (17)	0.0590 (19)	0.0445 (17)	−0.0078 (14)	−0.0138 (14)	−0.0055 (14)
C19	0.0616 (19)	0.0490 (17)	0.0413 (16)	−0.0051 (14)	−0.0195 (14)	−0.0034 (13)
C20	0.0542 (19)	0.0549 (18)	0.0452 (18)	−0.0018 (14)	−0.0160 (15)	−0.0083 (14)
C21	0.0502 (16)	0.0573 (18)	0.0492 (17)	−0.0058 (14)	−0.0231 (14)	−0.0055 (14)
C22	0.105 (3)	0.112 (3)	0.106 (3)	0.049 (3)	−0.059 (3)	−0.046 (3)
C23	0.089 (3)	0.156 (4)	0.080 (3)	−0.039 (3)	−0.048 (2)	0.042 (3)
C24	0.122 (3)	0.080 (3)	0.140 (4)	−0.012 (2)	−0.085 (3)	−0.021 (3)

Geometric parameters (Å, º) top

O1—C7	1.360 (3)	C11—H11A	0.9600
O1—C1	1.386 (3)	C11—H11B	0.9600
O2—N3	1.414 (3)	C11—H11C	0.9600
O2—C13	1.425 (3)	C12—H12	0.9300
O3—C20	1.210 (3)	C13—C14	1.507 (4)
O4—C20	1.316 (3)	C13—H13A	0.9700
O4—C21	1.471 (3)	C13—H13B	0.9700
N1—C7	1.332 (4)	C14—C19	1.373 (4)
N1—N2	1.355 (3)	C14—C15	1.388 (4)
N1—C11	1.458 (4)	C15—C16	1.373 (4)
N2—C9	1.331 (4)	C15—H15	0.9300
N3—C12	1.268 (3)	C16—C17	1.377 (4)
C1—C2	1.370 (4)	C16—H16	0.9300
C1—C6	1.371 (4)	C17—C18	1.386 (4)
C2—C3	1.380 (4)	C17—C20	1.487 (4)
C2—H2	0.9300	C18—C19	1.373 (4)
C3—C4	1.358 (4)	C18—H18	0.9300
C3—H3	0.9300	C19—H19	0.9300
C4—C5	1.361 (4)	C21—C24	1.487 (5)
C4—H4	0.9300	C21—C23	1.499 (4)
C5—C6	1.379 (4)	C21—C22	1.500 (5)
C5—H5	0.9300	C22—H22A	0.9600
C6—H6	0.9300	C22—H22B	0.9600
C7—C8	1.377 (4)	C22—H22C	0.9600
C8—C9	1.413 (4)	C23—H23A	0.9600
C8—C12	1.436 (4)	C23—H23B	0.9600
C9—C10	1.489 (4)	C23—H23C	0.9600
C10—H10A	0.9600	C24—H24A	0.9600
C10—H10B	0.9600	C24—H24B	0.9600
C10—H10C	0.9600	C24—H24C	0.9600

C7—O1—C1	119.0 (2)	O2—C13—H13A	108.8
N3—O2—C13	108.3 (2)	C14—C13—H13A	108.8
C20—O4—C21	122.9 (2)	O2—C13—H13B	108.8
C7—N1—N2	111.3 (2)	C14—C13—H13B	108.8
C7—N1—C11	128.0 (3)	H13A—C13—H13B	107.7
N2—N1—C11	120.7 (3)	C19—C14—C15	118.4 (3)
C9—N2—N1	105.4 (2)	C19—C14—C13	123.2 (3)
C12—N3—O2	110.3 (2)	C15—C14—C13	118.4 (3)
C2—C1—C6	121.1 (3)	C16—C15—C14	121.0 (3)
C2—C1—O1	114.9 (2)	C16—C15—H15	119.5
C6—C1—O1	123.9 (2)	C14—C15—H15	119.5
C1—C2—C3	118.8 (3)	C15—C16—C17	120.4 (3)
C1—C2—H2	120.6	C15—C16—H16	119.8
C3—C2—H2	120.6	C17—C16—H16	119.8
C4—C3—C2	120.8 (3)	C16—C17—C18	118.6 (3)
C4—C3—H3	119.6	C16—C17—C20	122.8 (3)
C2—C3—H3	119.6	C18—C17—C20	118.6 (3)
C3—C4—C5	119.7 (3)	C19—C18—C17	120.8 (3)
C3—C4—H4	120.2	C19—C18—H18	119.6
C5—C4—H4	120.2	C17—C18—H18	119.6
C4—C5—C6	121.0 (3)	C18—C19—C14	120.8 (3)
C4—C5—H5	119.5	C18—C19—H19	119.6
C6—C5—H5	119.5	C14—C19—H19	119.6
C1—C6—C5	118.5 (3)	O3—C20—O4	124.4 (3)
C1—C6—H6	120.7	O3—C20—C17	123.4 (3)
C5—C6—H6	120.7	O4—C20—C17	112.1 (3)
N1—C7—O1	121.8 (2)	O4—C21—C24	108.7 (2)
N1—C7—C8	108.6 (3)	O4—C21—C23	102.6 (2)
O1—C7—C8	129.4 (3)	C24—C21—C23	111.6 (3)
C7—C8—C9	103.6 (3)	O4—C21—C22	111.5 (2)
C7—C8—C12	125.5 (3)	C24—C21—C22	112.2 (3)
C9—C8—C12	130.9 (2)	C23—C21—C22	109.9 (3)
N2—C9—C8	111.1 (2)	C21—C22—H22A	109.5
N2—C9—C10	120.4 (3)	C21—C22—H22B	109.5
C8—C9—C10	128.5 (3)	H22A—C22—H22B	109.5
C9—C10—H10A	109.5	C21—C22—H22C	109.5
C9—C10—H10B	109.5	H22A—C22—H22C	109.5
H10A—C10—H10B	109.5	H22B—C22—H22C	109.5
C9—C10—H10C	109.5	C21—C23—H23A	109.5
H10A—C10—H10C	109.5	C21—C23—H23B	109.5
H10B—C10—H10C	109.5	H23A—C23—H23B	109.5
N1—C11—H11A	109.5	C21—C23—H23C	109.5
N1—C11—H11B	109.5	H23A—C23—H23C	109.5
H11A—C11—H11B	109.5	H23B—C23—H23C	109.5
N1—C11—H11C	109.5	C21—C24—H24A	109.5
H11A—C11—H11C	109.5	C21—C24—H24B	109.5
H11B—C11—H11C	109.5	H24A—C24—H24B	109.5
N3—C12—C8	121.5 (3)	C21—C24—H24C	109.5
N3—C12—H12	119.3	H24A—C24—H24C	109.5
C8—C12—H12	119.3	H24B—C24—H24C	109.5
O2—C13—C14	114.0 (2)

C7—N1—N2—C9	−0.4 (3)	C7—C8—C9—C10	−176.7 (3)
C11—N1—N2—C9	177.3 (3)	C12—C8—C9—C10	1.2 (5)
C13—O2—N3—C12	−172.9 (2)	O2—N3—C12—C8	−178.9 (2)
C7—O1—C1—C2	−171.4 (2)	C7—C8—C12—N3	−160.1 (3)
C7—O1—C1—C6	10.0 (4)	C9—C8—C12—N3	22.4 (4)
C6—C1—C2—C3	−0.9 (4)	N3—O2—C13—C14	−73.9 (3)
O1—C1—C2—C3	−179.5 (3)	O2—C13—C14—C19	−3.9 (4)
C1—C2—C3—C4	0.2 (5)	O2—C13—C14—C15	176.7 (3)
C2—C3—C4—C5	0.4 (5)	C19—C14—C15—C16	0.7 (5)
C3—C4—C5—C6	−0.3 (5)	C13—C14—C15—C16	−179.9 (3)
C2—C1—C6—C5	0.9 (4)	C14—C15—C16—C17	−1.3 (5)
O1—C1—C6—C5	179.5 (2)	C15—C16—C17—C18	0.8 (4)
C4—C5—C6—C1	−0.3 (4)	C15—C16—C17—C20	179.0 (3)
N2—N1—C7—O1	−173.2 (2)	C16—C17—C18—C19	0.3 (4)
C11—N1—C7—O1	9.3 (4)	C20—C17—C18—C19	−178.0 (3)
N2—N1—C7—C8	1.2 (3)	C17—C18—C19—C14	−0.8 (4)
C11—N1—C7—C8	−176.3 (3)	C15—C14—C19—C18	0.4 (4)
C1—O1—C7—N1	−93.0 (3)	C13—C14—C19—C18	−179.1 (3)
C1—O1—C7—C8	93.9 (3)	C21—O4—C20—O3	2.1 (5)
N1—C7—C8—C9	−1.4 (3)	C21—O4—C20—C17	−175.1 (2)
O1—C7—C8—C9	172.5 (3)	C16—C17—C20—O3	177.0 (3)
N1—C7—C8—C12	−179.4 (2)	C18—C17—C20—O3	−4.8 (4)
O1—C7—C8—C12	−5.6 (4)	C16—C17—C20—O4	−5.7 (4)
N1—N2—C9—C8	−0.5 (3)	C18—C17—C20—O4	172.4 (2)
N1—N2—C9—C10	177.6 (2)	C20—O4—C21—C24	65.5 (4)
C7—C8—C9—N2	1.2 (3)	C20—O4—C21—C23	−176.2 (3)
C12—C8—C9—N2	179.0 (3)	C20—O4—C21—C22	−58.7 (4)

Experimental details

Crystal data
Chemical formula	C₂₄H₂₇N₃O₄
M_r	421.49
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	9.672 (3), 9.908 (3), 13.179 (3)
α, β, γ (°)	72.487 (5), 71.614 (5), 74.494 (4)
V (Å³)	1122.0 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.32 × 0.24 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.972, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	5754, 3941, 2284
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.175, 1.06
No. of reflections	3941
No. of parameters	284
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.22

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999).

Acknowledgements

This work was supported by the National Key Project for Basic Research (No. 20772067).

References

Bruker (1999). SMART (Version 5.618), SAINT (Version 6.45), SADABS and SHELXTL (Version 6.1). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lewis, R. J., Camilleri, P., Kirby, A. J., Marby, C. A., Slawin, A. A. & Williams, D. J. (1991). J. Chem. Soc. Perkin Trans. 2, pp. 1625–1631. CSD CrossRef Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Zou, X.-M., Lin, D., Pei, J., Wang, C.-Q. & Yang, H.-Z. (2006). Acta Cryst. E62, o2471–o2472. Web of Science CSD CrossRef IUCr Journals Google Scholar

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