3-tert-Butyl-4-oxo-3,4-dihydro­phthalazin-1-yl 3,5-dimethyl­benzoate

Wu, D.-X.; Chen, Z.-W.; Ren, Y.-G.; Huang, M.-Z.

doi:10.1107/S1600536807061089

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o8

https://doi.org/10.1107/S1600536807061089

Open

access

3-tert-Butyl-4-oxo-3,4-dihydrophthalazin-1-yl 3,5-dimethylbenzoate

Dao-Xin Wu,^a ^* Zheng-Wang Chen,^b Ye-Guo Ren ^c and Ming-Zhi Huang ^c

^aChangsha University of Science and Technology, Changsha, Hunan 410076, People's Republic of China, ^bCollege of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, People's Republic of China, and ^cHunan Research Institute of Chemical Industry, Changsha 410007, People's Republic of China
^*Correspondence e-mail: daoxinwu@163.com

(Received 16 November 2007; accepted 20 November 2007; online 6 December 2007)

The title compound, C₂₁H₂₂N₂O₃, was synthesized by the reaction of tert-butylhydrazine with phthalic anhydride and further O-benzoylation of the resulting intermediate by 3,5-dimethylbenzoyl chloride. Intermolecular C—H⋯O=C interactions link the molecules into layers.

Related literature

For ecdysone agonists, see: Wing (1988 ). For the synthesis, see: Hou et al. (2002 ). For C—N bond lengths, see: Sasada (1984 ).

Experimental

Crystal data

C₂₁H₂₂N₂O₃
M_r = 350.41
Monoclinic, P 2₁ /n
a = 8.7974 (2) Å
b = 18.7622 (4) Å
c = 11.7405 (3) Å
β = 92.634 (2)°
V = 1935.82 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 (2) K
0.54 × 0.52 × 0.48 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: none
14969 measured reflections
3804 independent reflections
2879 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.137
S = 1.06
3804 reflections
241 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1ⁱ	0.93	2.56	3.391 (2)	149
C12—H12⋯O3ⁱⁱ	0.93	2.27	3.149 (2)	157
Symmetry codes: (i) -x, -y, -z; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 2000); 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, 1997 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807061089/ln2004sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807061089/ln2004Isup2.hkl

checkCIF report

Comment top

DibendzoyIhydrazines insect growth regulators are well known as nonsteroidal ecdysone agonists, which induce prematurely abnormal and ultimately lethal larval molting (Wing, 1988). The title compound, (I), was obtained unintentionally as the product of an attempted synthesis of a dibendzoylhydrazine and we present its crystal structure here. The molecular structure of (I) is shown in Fig.1. The bond length of C18—N2 [1.517 (2) Å] is slightly greater than the normal value of C—N [1.47 Å; Sasada, 1984] because of the larger terminal group tert-butyl moiety. The crystal structure of (I) also involves two weak C—H···O?C hydrogen-bonding interactions, which link the molecules into layers which lie parallel to the (101) plane. (Fig. 2 and Table 1).

Related literature top

For ecdysone agonists, see: Wing (1988). For the synthesis, see: Hou et al. (2002). For C—N bond lengths, see: Sasada (1984).

Experimental top

Phthalic anhydride (0.015 mol) was heated to 323 K in acetic acid, tert-butyldrazine (0.015 mol) was added dropwise, the solution was stirred for 3 h at 383 K. Then the mixture was condensed and washed with water and filtered, which afforded 2-tert-butyl-4-hydroxyphthalazin-1(2H)-one (m.p. 391–393 K). This compound (0.01 mol) was heated to 333 K in butyl acetate (30 ml) and water (20 ml) in the presence of DMPA catalyst (0.1 g), 3,5-Dimethylbenzoyl chloride (0.01 mol) and a saturated solution of Na₂CO₃(0.02 mol) which were added dropwise, then the mixture reacted for 4 h (Hou et al., 2002). The solution was cooled, washed with water and dried. The product was concentrated and purified by column chromatography (silica gel, petroleum ether-acetate 10:1) to give the title compound, (I) (yield 46%, m.p. 421–422 K). 1H NMR (CDCl3, δ, p.p.m): 1.71 (9H, s), 2.43 (6H, s), 7.33–7.26 (1H, s), 7.74–7.57 (1H, s), 7.79–7.75 (2H, m), 7.90–7.89 (2H, s), 8.46–8.43 (1H, m). Compound (I) was recrystallized from ethyl acetate. Single crystals of (I), suitable for X-ray analysis, were grown by natural evaporation of the solvent.

Structure description top

For ecdysone agonists, see: Wing (1988). For the synthesis, see: Hou et al. (2002). For C—N bond lengths, see: Sasada (1984).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).

Figures top

	Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The crystal structure of (I), viewed along the a axis. The dashed lines indicate C—H···O interations.

3-tert-Butyl-4-oxo-3,4-dihydrophthalazin-1-yl 3,5-dimethylbenzoate top

Crystal data top

C₂₁H₂₂N₂O₃	F(000) = 744
M_r = 350.41	D_x = 1.202 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4673 reflections
a = 8.7974 (2) Å	θ = 2.6–26.8°
b = 18.7622 (4) Å	µ = 0.08 mm⁻¹
c = 11.7405 (3) Å	T = 296 K
β = 92.634 (2)°	Block, colourless
V = 1935.82 (8) Å³	0.54 × 0.52 × 0.48 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2879 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.024
Graphite monochromator	θ_max = 26.0°, θ_min = 2.2°
phi and ω scans	h = −8→10
14969 measured reflections	k = −23→23
3804 independent reflections	l = −14→14

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.137	w = 1/[σ²(F_o²) + (0.0654P)² + 0.3695P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
3804 reflections	Δρ_max = 0.23 e Å⁻³
241 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.020 (2)

Crystal data top

C₂₁H₂₂N₂O₃	V = 1935.82 (8) Å³
M_r = 350.41	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.7974 (2) Å	µ = 0.08 mm⁻¹
b = 18.7622 (4) Å	T = 296 K
c = 11.7405 (3) Å	0.54 × 0.52 × 0.48 mm
β = 92.634 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2879 reflections with I > 2σ(I)
14969 measured reflections	R_int = 0.024
3804 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.06	Δρ_max = 0.23 e Å⁻³
3804 reflections	Δρ_min = −0.21 e Å⁻³
241 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
C1	−0.1890 (3)	−0.01591 (13)	0.3028 (2)	0.0934 (7)
H1A	−0.2610	−0.0137	0.2389	0.140*
H1B	−0.2406	−0.0080	0.3720	0.140*
H1C	−0.1417	−0.0620	0.3055	0.140*
C2	−0.06900 (19)	0.04061 (9)	0.29032 (15)	0.0586 (4)
C3	−0.0157 (2)	0.08071 (10)	0.38294 (14)	0.0628 (5)
H3	−0.0547	0.0720	0.4539	0.075*
C4	0.0936 (2)	0.13334 (9)	0.37380 (13)	0.0563 (4)
C5	0.1455 (3)	0.17747 (12)	0.47572 (16)	0.0809 (6)
H5A	0.0757	0.1714	0.5354	0.121*
H5B	0.1487	0.2268	0.4543	0.121*
H5C	0.2452	0.1623	0.5022	0.121*
C6	0.15174 (18)	0.14558 (8)	0.26761 (13)	0.0484 (4)
H6	0.2263	0.1801	0.2594	0.058*
C7	0.09907 (16)	0.10652 (8)	0.17396 (12)	0.0438 (3)
C8	−0.01108 (17)	0.05444 (9)	0.18535 (14)	0.0509 (4)
H8	−0.0461	0.0287	0.1218	0.061*
C9	0.15521 (17)	0.11830 (8)	0.05858 (13)	0.0463 (4)
C10	0.33337 (17)	0.17600 (8)	−0.04896 (12)	0.0468 (4)
C11	0.26329 (16)	0.22905 (8)	−0.12040 (12)	0.0463 (4)
C12	0.14226 (19)	0.27236 (10)	−0.09065 (14)	0.0578 (4)
H12	0.1017	0.2681	−0.0192	0.069*
C13	0.0840 (2)	0.32105 (11)	−0.16753 (17)	0.0676 (5)
H13	0.0035	0.3500	−0.1478	0.081*
C14	0.1433 (2)	0.32802 (10)	−0.27457 (17)	0.0662 (5)
H14	0.1015	0.3610	−0.3262	0.079*
C15	0.26313 (19)	0.28648 (9)	−0.30426 (14)	0.0561 (4)
H15	0.3034	0.2916	−0.3757	0.067*
C16	0.32475 (16)	0.23645 (8)	−0.22752 (12)	0.0465 (4)
C17	0.45363 (18)	0.19228 (9)	−0.25804 (13)	0.0536 (4)
C18	0.65359 (19)	0.10239 (10)	−0.19097 (16)	0.0624 (5)
C19	0.6200 (3)	0.04906 (15)	−0.2852 (2)	0.1083 (9)
H19A	0.7114	0.0237	−0.3011	0.163*
H19B	0.5830	0.0736	−0.3526	0.163*
H19C	0.5443	0.0160	−0.2618	0.163*
C20	0.7848 (2)	0.15067 (13)	−0.2199 (3)	0.0987 (8)
H20A	0.8019	0.1851	−0.1602	0.148*
H20B	0.7603	0.1749	−0.2904	0.148*
H20C	0.8750	0.1226	−0.2275	0.148*
C21	0.6985 (3)	0.06425 (15)	−0.0799 (2)	0.1006 (8)
H21A	0.7924	0.0391	−0.0883	0.151*
H21B	0.6202	0.0310	−0.0619	0.151*
H21C	0.7112	0.0986	−0.0196	0.151*
N1	0.44872 (15)	0.13807 (7)	−0.07117 (11)	0.0521 (3)
N2	0.51350 (15)	0.14770 (7)	−0.17419 (11)	0.0531 (4)
O1	0.10477 (15)	0.09179 (7)	−0.02755 (9)	0.0687 (4)
O2	0.27700 (12)	0.16353 (6)	0.05844 (8)	0.0525 (3)
O3	0.50744 (16)	0.19522 (9)	−0.35226 (10)	0.0811 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0836 (15)	0.1065 (17)	0.0913 (15)	−0.0374 (13)	0.0168 (12)	0.0187 (13)
C2	0.0530 (9)	0.0635 (10)	0.0599 (10)	−0.0050 (8)	0.0100 (8)	0.0118 (8)
C3	0.0667 (11)	0.0748 (12)	0.0481 (9)	0.0025 (9)	0.0174 (8)	0.0133 (9)
C4	0.0660 (11)	0.0594 (10)	0.0438 (8)	0.0052 (8)	0.0057 (7)	0.0035 (7)
C5	0.1118 (17)	0.0858 (14)	0.0454 (10)	−0.0070 (12)	0.0064 (10)	−0.0040 (9)
C6	0.0504 (9)	0.0490 (8)	0.0461 (8)	−0.0003 (7)	0.0052 (6)	0.0036 (7)
C7	0.0421 (8)	0.0469 (8)	0.0428 (7)	0.0039 (6)	0.0067 (6)	0.0030 (6)
C8	0.0482 (9)	0.0533 (9)	0.0516 (9)	−0.0023 (7)	0.0051 (7)	0.0016 (7)
C9	0.0461 (8)	0.0484 (8)	0.0448 (8)	−0.0023 (6)	0.0054 (6)	−0.0002 (7)
C10	0.0441 (8)	0.0591 (9)	0.0379 (7)	−0.0071 (7)	0.0091 (6)	−0.0019 (7)
C11	0.0410 (8)	0.0560 (9)	0.0423 (8)	−0.0064 (6)	0.0072 (6)	−0.0055 (7)
C12	0.0516 (9)	0.0696 (11)	0.0533 (9)	0.0013 (8)	0.0153 (7)	−0.0044 (8)
C13	0.0540 (10)	0.0737 (12)	0.0757 (12)	0.0110 (9)	0.0101 (9)	−0.0027 (10)
C14	0.0611 (11)	0.0718 (11)	0.0650 (11)	0.0046 (9)	−0.0037 (9)	0.0100 (9)
C15	0.0551 (10)	0.0677 (10)	0.0459 (8)	−0.0044 (8)	0.0046 (7)	0.0018 (8)
C16	0.0420 (8)	0.0576 (9)	0.0401 (7)	−0.0058 (7)	0.0060 (6)	−0.0031 (7)
C17	0.0480 (9)	0.0685 (10)	0.0452 (8)	−0.0028 (8)	0.0126 (7)	−0.0021 (8)
C18	0.0509 (10)	0.0663 (11)	0.0710 (11)	0.0090 (8)	0.0148 (8)	−0.0055 (9)
C19	0.0810 (16)	0.1075 (18)	0.136 (2)	0.0210 (14)	0.0026 (15)	−0.0579 (17)
C20	0.0515 (12)	0.0989 (17)	0.148 (2)	0.0077 (11)	0.0250 (13)	0.0081 (16)
C21	0.0916 (17)	0.1129 (19)	0.0984 (17)	0.0488 (15)	0.0183 (13)	0.0172 (14)
N1	0.0488 (8)	0.0610 (8)	0.0472 (7)	−0.0021 (6)	0.0103 (6)	0.0013 (6)
N2	0.0481 (8)	0.0622 (8)	0.0501 (7)	0.0044 (6)	0.0150 (6)	0.0003 (6)
O1	0.0797 (9)	0.0804 (9)	0.0463 (6)	−0.0271 (7)	0.0065 (6)	−0.0067 (6)
O2	0.0512 (6)	0.0686 (7)	0.0383 (5)	−0.0120 (5)	0.0102 (4)	−0.0012 (5)
O3	0.0777 (9)	0.1161 (11)	0.0520 (7)	0.0211 (8)	0.0310 (6)	0.0112 (7)

Geometric parameters (Å, º) top

C1—C2	1.508 (3)	C12—C13	1.367 (3)
C1—H1A	0.9600	C12—H12	0.9300
C1—H1B	0.9600	C13—C14	1.389 (3)
C1—H1C	0.9600	C13—H13	0.9300
C2—C8	1.380 (2)	C14—C15	1.369 (2)
C2—C3	1.386 (3)	C14—H14	0.9300
C3—C4	1.386 (2)	C15—C16	1.393 (2)
C3—H3	0.9300	C15—H15	0.9300
C4—C6	1.388 (2)	C16—C17	1.462 (2)
C4—C5	1.509 (3)	C17—O3	1.2243 (18)
C5—H5A	0.9600	C17—N2	1.378 (2)
C5—H5B	0.9600	C18—C19	1.511 (3)
C5—H5C	0.9600	C18—N2	1.517 (2)
C6—C7	1.383 (2)	C18—C20	1.518 (3)
C6—H6	0.9300	C18—C21	1.523 (3)
C7—C8	1.387 (2)	C19—H19A	0.9600
C7—C9	1.4796 (19)	C19—H19B	0.9600
C8—H8	0.9300	C19—H19C	0.9600
C9—O1	1.1939 (18)	C20—H20A	0.9600
C9—O2	1.3668 (18)	C20—H20B	0.9600
C10—N1	1.276 (2)	C20—H20C	0.9600
C10—O2	1.3958 (17)	C21—H21A	0.9600
C10—C11	1.424 (2)	C21—H21B	0.9600
C11—C16	1.3985 (19)	C21—H21C	0.9600
C11—C12	1.397 (2)	N1—N2	1.3725 (17)

C2—C1—H1A	109.5	C12—C13—H13	119.5
C2—C1—H1B	109.5	C14—C13—H13	119.5
H1A—C1—H1B	109.5	C15—C14—C13	120.16 (17)
C2—C1—H1C	109.5	C15—C14—H14	119.9
H1A—C1—H1C	109.5	C13—C14—H14	119.9
H1B—C1—H1C	109.5	C14—C15—C16	120.01 (15)
C8—C2—C3	118.23 (15)	C14—C15—H15	120.0
C8—C2—C1	120.53 (17)	C16—C15—H15	120.0
C3—C2—C1	121.24 (16)	C15—C16—C11	119.56 (14)
C2—C3—C4	122.48 (15)	C15—C16—C17	120.42 (14)
C2—C3—H3	118.8	C11—C16—C17	120.02 (14)
C4—C3—H3	118.8	O3—C17—N2	121.47 (15)
C3—C4—C6	118.23 (15)	O3—C17—C16	122.15 (16)
C3—C4—C5	121.03 (16)	N2—C17—C16	116.37 (13)
C6—C4—C5	120.73 (16)	C19—C18—N2	109.48 (15)
C4—C5—H5A	109.5	C19—C18—C20	110.88 (19)
C4—C5—H5B	109.5	N2—C18—C20	108.96 (15)
H5A—C5—H5B	109.5	C19—C18—C21	110.5 (2)
C4—C5—H5C	109.5	N2—C18—C21	109.42 (14)
H5A—C5—H5C	109.5	C20—C18—C21	107.58 (19)
H5B—C5—H5C	109.5	C18—C19—H19A	109.5
C7—C6—C4	120.15 (15)	C18—C19—H19B	109.5
C7—C6—H6	119.9	H19A—C19—H19B	109.5
C4—C6—H6	119.9	C18—C19—H19C	109.5
C6—C7—C8	120.43 (14)	H19A—C19—H19C	109.5
C6—C7—C9	122.33 (13)	H19B—C19—H19C	109.5
C8—C7—C9	117.24 (13)	C18—C20—H20A	109.5
C2—C8—C7	120.47 (15)	C18—C20—H20B	109.5
C2—C8—H8	119.8	H20A—C20—H20B	109.5
C7—C8—H8	119.8	C18—C20—H20C	109.5
O1—C9—O2	121.23 (13)	H20A—C20—H20C	109.5
O1—C9—C7	125.91 (14)	H20B—C20—H20C	109.5
O2—C9—C7	112.86 (12)	C18—C21—H21A	109.5
N1—C10—O2	114.20 (14)	C18—C21—H21B	109.5
N1—C10—C11	126.62 (13)	H21A—C21—H21B	109.5
O2—C10—C11	119.16 (13)	C18—C21—H21C	109.5
C16—C11—C12	119.86 (15)	H21A—C21—H21C	109.5
C16—C11—C10	115.11 (13)	H21B—C21—H21C	109.5
C12—C11—C10	125.03 (14)	C10—N1—N2	118.22 (13)
C13—C12—C11	119.38 (15)	N1—N2—C17	123.30 (13)
C13—C12—H12	120.3	N1—N2—C18	114.41 (13)
C11—C12—H12	120.3	C17—N2—C18	122.24 (13)
C12—C13—C14	121.03 (17)	C9—O2—C10	114.60 (11)

C8—C2—C3—C4	−0.5 (3)	C12—C11—C16—C15	−0.8 (2)
C1—C2—C3—C4	−179.50 (18)	C10—C11—C16—C15	179.37 (14)
C2—C3—C4—C6	−0.4 (3)	C12—C11—C16—C17	178.66 (14)
C2—C3—C4—C5	178.11 (18)	C10—C11—C16—C17	−1.1 (2)
C3—C4—C6—C7	0.9 (2)	C15—C16—C17—O3	−3.2 (3)
C5—C4—C6—C7	−177.60 (16)	C11—C16—C17—O3	177.35 (16)
C4—C6—C7—C8	−0.6 (2)	C15—C16—C17—N2	175.80 (14)
C4—C6—C7—C9	178.92 (14)	C11—C16—C17—N2	−3.7 (2)
C3—C2—C8—C7	0.9 (2)	O2—C10—N1—N2	−178.84 (12)
C1—C2—C8—C7	179.90 (17)	C11—C10—N1—N2	−0.7 (2)
C6—C7—C8—C2	−0.4 (2)	C10—N1—N2—C17	−5.0 (2)
C9—C7—C8—C2	−179.87 (14)	C10—N1—N2—C18	177.70 (14)
C6—C7—C9—O1	−172.15 (16)	O3—C17—N2—N1	−174.04 (16)
C8—C7—C9—O1	7.3 (2)	C16—C17—N2—N1	7.0 (2)
C6—C7—C9—O2	8.7 (2)	O3—C17—N2—C18	3.0 (3)
C8—C7—C9—O2	−171.80 (13)	C16—C17—N2—C18	−175.93 (14)
N1—C10—C11—C16	3.6 (2)	C19—C18—N2—N1	113.71 (19)
O2—C10—C11—C16	−178.33 (13)	C20—C18—N2—N1	−124.88 (18)
N1—C10—C11—C12	−176.22 (16)	C21—C18—N2—N1	−7.5 (2)
O2—C10—C11—C12	1.9 (2)	C19—C18—N2—C17	−63.6 (2)
C16—C11—C12—C13	0.8 (2)	C20—C18—N2—C17	57.8 (2)
C10—C11—C12—C13	−179.44 (16)	C21—C18—N2—C17	175.19 (18)
C11—C12—C13—C14	0.0 (3)	O1—C9—O2—C10	0.8 (2)
C12—C13—C14—C15	−0.8 (3)	C7—C9—O2—C10	179.99 (12)
C13—C14—C15—C16	0.8 (3)	N1—C10—O2—C9	−97.91 (16)
C14—C15—C16—C11	0.1 (2)	C11—C10—O2—C9	83.76 (17)
C14—C15—C16—C17	−179.44 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1ⁱ	0.93	2.56	3.391 (2)	149
C12—H12···O3ⁱⁱ	0.93	2.27	3.149 (2)	157

Symmetry codes: (i) −x, −y, −z; (ii) x−1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₂N₂O₃
M_r	350.41
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	8.7974 (2), 18.7622 (4), 11.7405 (3)
β (°)	92.634 (2)
V (Å³)	1935.82 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.54 × 0.52 × 0.48

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	14969, 3804, 2879
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.137, 1.06
No. of reflections	3804
No. of parameters	241
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.21

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1ⁱ	0.93	2.56	3.391 (2)	149
C12—H12···O3ⁱⁱ	0.93	2.27	3.149 (2)	157

Symmetry codes: (i) −x, −y, −z; (ii) x−1/2, −y+1/2, z+1/2.

Acknowledgements

The authors acknowledge financial support from the National Eleventh–Five Key Project of the People's Republic of China (2006BAE01A01-4).

References

Bruker (1997). SHELXTL. Version 6.12. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2000). SMART (Version 5.059) and SAINT (Version 6.01). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hou, Z.-K., Ren, Y.-G. & Zhang, L.-J. (2002). Chin. J. Pestic. Sci. 4, 72–74. CAS Google Scholar
Sasada, Y. (1984). Molecular and Crystal Structure in Chemistry Handbook, 3rd ed. Tokyo: Maruzen Press/The Chemistry Society of Japan. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXS97. University of Göttingen, Germany. Google Scholar
Wing, K. D. (1988). Science, 241, 467–469. CrossRef CAS PubMed Web of Science Google Scholar