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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 8| August 2009| Page o2015
doi:10.1107/S1600536809028815

N′-tert-Butyl-N′-(3,5-di­methyl­benzo­yl)-2,2-di­methyl-4-oxochroman-6-carbo­hydrazide

Zhongzhen Zhou,a Wenwei You,a Zhongkun Tanga and Peiliang Zhaoa*

aSchool of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515, People's Republic of China
*Correspondence e-mail: peiliangzhao1999@yahoo.com.cn

(Received 7 July 2009; accepted 21 July 2009; online 29 July 2009)

In the crystal structure of the title compound, C25H30N2O4, the steric size of the tert-butyl group causes the 3,5-dimethyl­phenyl ring to adopt a transoid geometry with respect to the N—C(O) bond. The six-membered heterocyclic ring is disordered over two sites, with occupancies of 0.553 (4) and 0.447 (4). Intra­molecular C—H⋯O inter­actions are present. In the crystal, mol­ecules are linked by inter­molecular N—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For general background to dibenzoyl­hydrazines and their derivatives, see: Sawada et al. (2003[Sawada, Y., Yanai, T., Nakagawa, H., Kajino, F., Tsukamoto, Y., Yokoi, S., Yanagi, M., Sugizaki, H., Toya, T. & Masui, A. (2003). Pest Manag. Sci. 59, 49-57.]). For a related structure, see: Zhao et al. (2005[Zhao, P.-L., Huang, W. & Yang, G.-F. (2005). Acta Cryst. E61, o2139-o2141.]). For the preparation of the title compound, see: Zhao et al. (2007[Zhao, P. L., Li, J. & Yang, G. F. (2007). Bioorg. Med. Chem. 15, 1888-1895.]); Mao et al. (2008[Mao, C. H., Wang, K. L., Wang, Z. M., Qu, X., Huang, R. & Wang, Q. M. (2008). Bioorg. Med. Chem. 16, 488-494.]).

[Scheme 1]

Experimental

Crystal data

  • C25H30N2O4

  • Mr = 422.51

  • Monoclinic, P 21 /n

  • a = 14.1260 (12) Å

  • b = 10.6964 (9) Å

  • c = 15.4370 (13) Å

  • β = 96.426 (2)°

  • V = 2317.8 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 297 K

  • 0.30 × 0.20 × 0.20 mm
Data collection

  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2005[Sheldrick, G. M. (2005). SADABS. University of Göttingen, Germany.]) Tmin = 0.976, Tmax = 0.984

  • 13199 measured reflections

  • 5043 independent reflections

  • 3983 reflections with I > 2σ(I)

  • Rint = 0.020
Refinement

  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.142

  • S = 1.04

  • 5043 reflections

  • 338 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C16—H16C⋯O4 0.96 2.39 3.007 (2) 121
C15—H15A⋯O4 0.96 2.36 2.918 (2) 117
C8—H8⋯O4i 0.93 2.48 3.3214 (18) 151
N1—H1⋯O4i 0.862 (17) 2.096 (18) 2.9442 (15) 167.8 (15)
Symmetry code: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809028815/fj2236sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809028815/fj2236Isup2.hkl

checkCIF report


Comment top

Dibenzoylhydrazines are well known as nonsteroidal ecdysone agonists that have the potential to control the Lepidopteran pests while exerting only a low toxicity against non-target insects. (Sawada et al., 2003). While chroman derivatives also have broad-spectrum biological activity. Hence, to search for novel lead compounds for crop protection, The title compound, (I), was designed and synthesized in our laboratory. In this paper, we present the X-ray crystallographic analysis of (I).

As shown in Fig. 1, the six-membered heterocyclic ring adopts a half-chair conformation. the dihedral angle between the phenyl ring and the benzene ring of the chromanone is 58.14 (2)°. The six-memebered heterocyclic ring is disordered over two sites with occupancies of 0.553 (4) and 0.447 (4). The steric size of the N-tert-butyl group causes the 3,5-dimethylphenyl group to be directed away from it.

One intermolecular N—H···O hydrogen bond and one intermolecular C—H···O hydrogen bonds exist in the crystal structure (Table 1 and Fig. 2), atoms N1 and C8 in the molecule act as donors, via the H atoms H1 and H8, to the O4 of a adjacent molecule(Tabel 2). As a result, an seven-membered ring is formed between molecules (Fig. 2). No π-π stacking interactions are observed in the crystal structure.

Related literature top

For general background to dibenzoylhydrazines and their derivatives, see: Sawada et al. (2003). For a related structure, see: Zhao et al. (2005). For the preparation of the title compound, see: Zhao et al. (2007); Mao et al. (2008).

Experimental top

To A solution of 2,2-Dimethyl-4-oxo-chroman-6-carboxylic acid N'-tert-butyl-hydrazide (1.5 mmol) in 10 ml of dichloromethane was added dropwise to a stirred mixture of 3,5-dimethylbenzoyl chloride (1.5 mmol), triethylamine (1.6 mmol) and dichloromethane (5 ml) in an ice bath.After stirring the mixture at room temperature for 3 h,ethyl acetate (30 ml) was added to the reaction mixture. The organic layer was separated and washed successively with water (15 ml) and brine (15 ml), and then dried with anhydrous sodium sulfate. After evaporating the solvent, the residue was purified by column chromatography on silicagel using hexane/ethyl acetate (9:1 v/v) as eluent to afford (I) (yield 80%, m.p. 435 K) Spectroscopic analysis: 1H NMR(CDCl3, 400 MHz) 8.06 (s, 1H, N—H), 7.74 (d, 2H, C10—H, C11—H), 7.05 (s, 2H, C19—H, C23—H), 6.81 (m, 2H, C8—H, C21—H), 2.70 (s, 2H, C2—H), 2.21 (s, 6H, C24—H, C25—H), 1.57 (s, 9H, C14—H, C15—H,C16—H),1.44 (s, 6H, C6—H,C7—H); MS (EI 70 eV)m/z(%):422 (16), 367 (95), 349 (35), 203 (62), 146 (20),133 (100), 105 (49),102 (19). Crystals suitable for an X-ray diffraction study were grown from methanol at 292 K.

Refinement top

All H atoms were initially located in a difference Fourier map. The methyl H atoms were then constrained to an ideal geometry with C—H distances of 0.96 Å and Uiso(H) = 1.5Ueq(C), but each group was allowed to rotate freely about its C—C bond. All other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H distances in the range 0.93–0.97 Å,an N—H distance of 0.86 Å and Uiso(H) = 1.2Ueq(C,N).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented by circles of arbitrary size.
[Figure 2] Fig. 2. Hydrogen bonding in the crystal structure of (I).Hydrogen bonds are shown as dashed lines. [Symmetry codes: b. -x + 3/2,y + 1/2, -z + 1/2]
N'-tert-Butyl-N'-(3,5-dimethylbenzoyl)-2,2-dimethyl-4- oxochroman-6-carbohydrazide top
Crystal data top
C25H30N2O4F(000) = 904
Mr = 422.51Dx = 1.211 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5293 reflections
a = 14.1260 (12) Åθ = 2.3–27.9°
b = 10.6964 (9) ŵ = 0.08 mm−1
c = 15.4370 (13) ÅT = 297 K
β = 96.426 (2)°Block, colorless
V = 2317.8 (3) Å30.30 × 0.20 × 0.20 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		5043 independent reflections
Radiation source: fine-focus sealed tube3983 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
ϕ and ω scansθmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2005)		h = −18→18
Tmin = 0.976, Tmax = 0.984k = −13→13
13199 measured reflectionsl = −19→11
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0739P)2 + 0.3537P]
where P = (Fo2 + 2Fc2)/3
5043 reflections(Δ/σ)max = 0.027
338 parametersΔρmax = 0.22 e Å−3
0 restraintsΔρmin = −0.17 e Å−3
Crystal data top
C25H30N2O4V = 2317.8 (3) Å3
Mr = 422.51Z = 4
Monoclinic, P21/nMo Kα radiation
a = 14.1260 (12) ŵ = 0.08 mm−1
b = 10.6964 (9) ÅT = 297 K
c = 15.4370 (13) Å0.30 × 0.20 × 0.20 mm
β = 96.426 (2)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		5043 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2005)		3983 reflections with I > 2σ(I)
Tmin = 0.976, Tmax = 0.984Rint = 0.020
13199 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.142H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.22 e Å−3
5043 reflectionsΔρmin = −0.17 e Å−3
338 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
xyzUiso*/UeqOcc. (<1)
C30.66849 (13)1.10349 (14)−0.10449 (11)0.0605 (4)
C40.67622 (12)0.88189 (13)−0.00473 (10)0.0514 (4)
C50.68639 (11)0.87969 (14)−0.09323 (9)0.0494 (3)
C10.6450 (5)0.9997 (11)0.0354 (8)0.065 (2)0.553 (4)
O10.6346 (7)1.0033 (10)0.1119 (7)0.114 (3)0.553 (4)
C20.6193 (3)1.1038 (3)−0.0289 (2)0.0658 (10)0.553 (4)
H2A0.55151.0993−0.04750.079*0.553 (4)
H2B0.63141.18300.00090.079*0.553 (4)
C60.6317 (4)1.1921 (4)−0.1762 (3)0.0794 (12)0.553 (4)
H6A0.56571.1746−0.19400.119*0.553 (4)
H6B0.66761.1816−0.22490.119*0.553 (4)
H6C0.63821.2765−0.15530.119*0.553 (4)
C70.7797 (3)1.1317 (4)−0.0800 (3)0.0873 (13)0.553 (4)
H7A0.78751.2129−0.05370.131*0.553 (4)
H7B0.81121.1295−0.13190.131*0.553 (4)
H7C0.80691.0696−0.03980.131*0.553 (4)
C1'0.6818 (6)1.0036 (14)0.0428 (10)0.060 (2)0.447 (4)
O1'0.6711 (7)1.0167 (11)0.1174 (8)0.0697 (17)0.447 (4)
C2'0.7037 (4)1.1160 (4)−0.0090 (3)0.0685 (13)0.447 (4)
H2'10.77211.1291−0.00270.082*0.447 (4)
H2'20.67461.18900.01430.082*0.447 (4)
C7'0.5527 (3)1.0980 (4)−0.1099 (3)0.0755 (13)0.447 (4)
H7'10.53401.0260−0.07890.113*0.447 (4)
H7'20.52621.0926−0.16980.113*0.447 (4)
H7'30.52971.1722−0.08430.113*0.447 (4)
C6'0.6941 (6)1.2082 (6)−0.1583 (4)0.0936 (19)0.447 (4)
H6'10.67251.2850−0.13500.140*0.447 (4)
H6'20.66451.1974−0.21690.140*0.447 (4)
H6'30.76201.2110−0.15830.140*0.447 (4)
C80.68071 (12)0.77025 (13)0.04199 (10)0.0515 (4)
H80.67380.77190.10120.062*
C90.69514 (10)0.65732 (12)0.00237 (9)0.0440 (3)
C100.70566 (10)0.65759 (14)−0.08622 (9)0.0499 (3)
H100.71530.5823−0.11410.060*
C110.70207 (11)0.76656 (15)−0.13332 (10)0.0544 (4)
H110.71020.7646−0.19230.065*
C120.69536 (10)0.53436 (12)0.04860 (10)0.0468 (3)
C130.59930 (11)0.41391 (14)0.21344 (11)0.0538 (4)
C140.53721 (13)0.52843 (17)0.18794 (15)0.0753 (5)
H14A0.56730.60190.21400.113*
H14B0.47590.51780.20820.113*
H14C0.52960.53730.12570.113*
C150.60593 (14)0.39710 (18)0.31198 (13)0.0715 (5)
H15A0.63700.31930.32790.107*
H15B0.54300.39670.32990.107*
H15C0.64200.46470.34010.107*
C160.55686 (12)0.29932 (16)0.16431 (14)0.0702 (5)
H16A0.54960.31610.10280.105*
H16B0.49570.28080.18280.105*
H16C0.59850.22910.17640.105*
C170.76979 (10)0.35224 (11)0.20322 (9)0.0419 (3)
C180.86257 (9)0.37282 (12)0.16645 (9)0.0426 (3)
C190.91465 (10)0.48329 (13)0.17253 (10)0.0475 (3)
H190.89150.55250.20000.057*
C201.00090 (11)0.49090 (14)0.13791 (10)0.0530 (4)
C211.03369 (11)0.38643 (16)0.09734 (11)0.0582 (4)
H211.09060.39200.07250.070*
C220.98488 (11)0.27454 (15)0.09244 (11)0.0561 (4)
C230.89924 (10)0.26895 (13)0.12762 (10)0.0494 (3)
H230.86550.19420.12530.059*
C241.05961 (13)0.60902 (17)0.14489 (14)0.0745 (5)
H24A1.08450.62240.20460.112*
H24B1.02030.67860.12460.112*
H24C1.11130.60110.10990.112*
C251.02483 (16)0.16056 (19)0.05138 (16)0.0862 (6)
H25A1.06850.18640.01140.129*
H25B0.97370.11370.02060.129*
H25C1.05770.10920.09610.129*
N10.71169 (8)0.54096 (10)0.13664 (8)0.0442 (3)
H10.7207 (11)0.6105 (16)0.1645 (11)0.053*
N20.69837 (8)0.43704 (10)0.18823 (8)0.0448 (3)
O20.68091 (10)0.98341 (11)−0.14408 (8)0.0697 (4)
O30.68252 (10)0.43588 (10)0.00964 (8)0.0680 (3)
O40.75822 (7)0.25569 (9)0.24413 (7)0.0527 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C30.0823 (11)0.0413 (8)0.0569 (9)−0.0035 (7)0.0036 (8)0.0097 (7)
C40.0704 (9)0.0384 (7)0.0462 (8)0.0063 (6)0.0101 (7)0.0034 (6)
C50.0560 (8)0.0456 (8)0.0478 (8)0.0026 (6)0.0105 (6)0.0064 (6)
C10.100 (5)0.040 (2)0.059 (4)0.013 (4)0.027 (5)0.004 (2)
O10.236 (10)0.046 (3)0.070 (4)0.024 (5)0.064 (6)0.004 (2)
C20.092 (3)0.0395 (14)0.069 (2)0.0125 (15)0.0221 (18)0.0105 (13)
C60.114 (4)0.053 (2)0.070 (2)0.005 (2)0.007 (3)0.0194 (18)
C70.080 (2)0.066 (2)0.115 (3)−0.0203 (18)0.006 (2)0.008 (2)
C1'0.088 (6)0.043 (3)0.049 (3)0.014 (5)0.007 (5)0.0066 (19)
O1'0.121 (4)0.042 (3)0.045 (2)0.010 (2)0.008 (3)−0.0031 (18)
C2'0.090 (3)0.047 (2)0.066 (2)−0.0059 (19)−0.003 (2)−0.0011 (17)
C7'0.073 (3)0.078 (3)0.074 (3)0.015 (2)0.002 (2)0.008 (2)
C6'0.138 (6)0.068 (3)0.079 (4)−0.023 (4)0.030 (4)0.018 (3)
C80.0718 (10)0.0418 (7)0.0416 (7)0.0084 (7)0.0097 (7)0.0023 (6)
C90.0468 (7)0.0375 (7)0.0467 (7)0.0039 (5)0.0010 (6)0.0006 (6)
C100.0540 (8)0.0450 (8)0.0503 (8)0.0081 (6)0.0043 (6)−0.0066 (6)
C110.0645 (9)0.0576 (9)0.0427 (8)0.0072 (7)0.0129 (7)0.0002 (7)
C120.0518 (8)0.0355 (7)0.0519 (8)0.0041 (6)0.0012 (6)−0.0016 (6)
C130.0501 (8)0.0415 (7)0.0715 (10)0.0016 (6)0.0140 (7)−0.0001 (7)
C140.0567 (10)0.0608 (10)0.1105 (16)0.0147 (8)0.0189 (10)0.0057 (10)
C150.0796 (12)0.0646 (10)0.0756 (12)0.0033 (9)0.0318 (9)0.0017 (9)
C160.0560 (9)0.0571 (10)0.0980 (14)−0.0107 (8)0.0109 (9)−0.0075 (9)
C170.0512 (7)0.0313 (6)0.0425 (7)0.0004 (5)0.0026 (6)−0.0010 (5)
C180.0481 (7)0.0369 (6)0.0416 (7)0.0041 (5)−0.0002 (5)0.0023 (5)
C190.0535 (8)0.0378 (7)0.0508 (8)0.0004 (6)0.0034 (6)−0.0028 (6)
C200.0506 (8)0.0504 (8)0.0570 (9)−0.0030 (6)0.0012 (6)0.0018 (7)
C210.0483 (8)0.0636 (10)0.0640 (10)0.0033 (7)0.0114 (7)−0.0005 (8)
C220.0562 (9)0.0530 (9)0.0592 (9)0.0098 (7)0.0069 (7)−0.0067 (7)
C230.0544 (8)0.0381 (7)0.0549 (8)0.0028 (6)0.0025 (6)−0.0028 (6)
C240.0652 (10)0.0628 (11)0.0964 (14)−0.0170 (8)0.0124 (10)−0.0043 (10)
C250.0850 (13)0.0685 (12)0.1098 (16)0.0131 (10)0.0317 (12)−0.0227 (11)
N10.0548 (7)0.0272 (5)0.0495 (7)0.0011 (5)0.0016 (5)0.0022 (5)
N20.0496 (6)0.0315 (5)0.0539 (7)0.0017 (5)0.0079 (5)0.0049 (5)
O20.1092 (10)0.0515 (6)0.0522 (6)0.0076 (6)0.0257 (6)0.0124 (5)
O30.1024 (9)0.0384 (6)0.0610 (7)0.0002 (6)−0.0009 (6)−0.0085 (5)
O40.0645 (6)0.0345 (5)0.0598 (6)0.0032 (4)0.0096 (5)0.0099 (4)
Geometric parameters (Å, º) top
C3—C21.423 (4)C11—H110.9300
C3—O21.4416 (19)C12—O31.2165 (17)
C3—C6'1.464 (5)C12—N11.3547 (19)
C3—C61.504 (4)C13—N21.5143 (18)
C3—C2'1.509 (4)C13—C151.524 (3)
C3—C71.602 (4)C13—C161.528 (2)
C3—C7'1.629 (5)C13—C141.532 (2)
C4—C51.390 (2)C14—H14A0.9600
C4—C81.3928 (19)C14—H14B0.9600
C4—C11.492 (11)C14—H14C0.9600
C4—C1'1.492 (15)C15—H15A0.9600
C5—O21.3562 (17)C15—H15B0.9600
C5—C111.388 (2)C15—H15C0.9600
C1—O11.207 (16)C16—H16A0.9600
C1—C21.509 (12)C16—H16B0.9600
C2—H2A0.9700C16—H16C0.9600
C2—H2B0.9700C17—O41.2310 (15)
C6—H6A0.9600C17—N21.3572 (17)
C6—H6B0.9600C17—C181.5016 (19)
C6—H6C0.9600C18—C191.3896 (19)
C7—H7A0.9600C18—C231.3898 (19)
C7—H7B0.9600C19—C201.387 (2)
C7—H7C0.9600C19—H190.9300
C1'—O1'1.186 (19)C20—C211.386 (2)
C1'—C2'1.495 (15)C20—C241.509 (2)
C2'—H2'10.9700C21—C221.379 (2)
C2'—H2'20.9700C21—H210.9300
C7'—H7'10.9600C22—C231.382 (2)
C7'—H7'20.9600C22—C251.512 (2)
C7'—H7'30.9600C23—H230.9300
C6'—H6'10.9600C24—H24A0.9600
C6'—H6'20.9600C24—H24B0.9600
C6'—H6'30.9600C24—H24C0.9600
C8—C91.3794 (19)C25—H25A0.9600
C8—H80.9300C25—H25B0.9600
C9—C101.392 (2)C25—H25C0.9600
C9—C121.4962 (18)N1—N21.3924 (15)
C10—C111.372 (2)N1—H10.862 (17)
C10—H100.9300
C2—C3—O2116.33 (16)C9—C10—H10119.3
C2—C3—C6'129.6 (3)C10—C11—C5120.18 (13)
O2—C3—C6'113.1 (3)C10—C11—H11119.9
C2—C3—C6116.2 (3)C5—C11—H11119.9
O2—C3—C6107.3 (2)O3—C12—N1122.71 (13)
C2—C3—C2'48.4 (2)O3—C12—C9122.21 (13)
O2—C3—C2'116.81 (19)N1—C12—C9115.07 (11)
C6'—C3—C2'114.3 (3)N2—C13—C15108.69 (13)
C6—C3—C2'135.4 (3)N2—C13—C16109.02 (12)
C2—C3—C7111.2 (3)C15—C13—C16112.19 (14)
O2—C3—C796.03 (19)N2—C13—C14108.80 (12)
C6'—C3—C772.1 (4)C15—C13—C14108.68 (15)
C6—C3—C7107.7 (3)C16—C13—C14109.40 (15)
C2'—C3—C762.9 (3)C13—C14—H14A109.5
C2—C3—C7'57.5 (2)C13—C14—H14B109.5
O2—C3—C7'96.6 (2)H14A—C14—H14B109.5
C6'—C3—C7'108.0 (4)C13—C14—H14C109.5
C6—C3—C7'73.9 (3)H14A—C14—H14C109.5
C2'—C3—C7'105.9 (3)H14B—C14—H14C109.5
C7—C3—C7'166.1 (3)C13—C15—H15A109.5
C5—C4—C8119.40 (13)C13—C15—H15B109.5
C5—C4—C1119.3 (5)H15A—C15—H15B109.5
C8—C4—C1120.5 (5)C13—C15—H15C109.5
C5—C4—C1'119.5 (6)H15A—C15—H15C109.5
C8—C4—C1'119.8 (6)H15B—C15—H15C109.5
O2—C5—C11117.17 (13)C13—C16—H16A109.5
O2—C5—C4123.34 (13)C13—C16—H16B109.5
C11—C5—C4119.48 (13)H16A—C16—H16B109.5
O1—C1—C4120.5 (10)C13—C16—H16C109.5
O1—C1—C2125.0 (10)H16A—C16—H16C109.5
C4—C1—C2114.3 (8)H16B—C16—H16C109.5
C3—C2—C1115.7 (4)O4—C17—N2120.62 (12)
C3—C2—H2A108.4O4—C17—C18119.25 (12)
C1—C2—H2A108.4N2—C17—C18120.08 (11)
C3—C2—H2B108.4C19—C18—C23119.26 (13)
C1—C2—H2B108.4C19—C18—C17125.24 (12)
H2A—C2—H2B107.4C23—C18—C17115.41 (12)
C3—C6—H6A109.5C20—C19—C18120.35 (13)
C3—C6—H6B109.5C20—C19—H19119.8
C3—C6—H6C109.5C18—C19—H19119.8
C3—C7—H7A109.5C21—C20—C19118.65 (14)
C3—C7—H7B109.5C21—C20—C24119.92 (15)
C3—C7—H7C109.5C19—C20—C24121.42 (14)
O1'—C1'—C4125.0 (12)C22—C21—C20122.29 (14)
O1'—C1'—C2'118.7 (12)C22—C21—H21118.9
C4—C1'—C2'116.2 (10)C20—C21—H21118.9
C1'—C2'—C3112.6 (6)C21—C22—C23118.06 (14)
C1'—C2'—H2'1109.1C21—C22—C25120.98 (15)
C3—C2'—H2'1109.1C23—C22—C25120.94 (15)
C1'—C2'—H2'2109.1C22—C23—C18121.33 (13)
C3—C2'—H2'2109.1C22—C23—H23119.3
H2'1—C2'—H2'2107.8C18—C23—H23119.3
C3—C7'—H7'1109.5C20—C24—H24A109.5
C3—C7'—H7'2109.5C20—C24—H24B109.5
H7'1—C7'—H7'2109.5H24A—C24—H24B109.5
C3—C7'—H7'3109.5C20—C24—H24C109.5
H7'1—C7'—H7'3109.5H24A—C24—H24C109.5
H7'2—C7'—H7'3109.5H24B—C24—H24C109.5
C3—C6'—H6'1109.5C22—C25—H25A109.5
C3—C6'—H6'2109.5C22—C25—H25B109.5
H6'1—C6'—H6'2109.5H25A—C25—H25B109.5
C3—C6'—H6'3109.5C22—C25—H25C109.5
H6'1—C6'—H6'3109.5H25A—C25—H25C109.5
H6'2—C6'—H6'3109.5H25B—C25—H25C109.5
C9—C8—C4121.44 (13)C12—N1—N2120.89 (11)
C9—C8—H8119.3C12—N1—H1123.0 (11)
C4—C8—H8119.3N2—N1—H1115.2 (11)
C8—C9—C10118.11 (12)C17—N2—N1119.06 (11)
C8—C9—C12123.42 (12)C17—N2—C13122.53 (11)
C10—C9—C12118.41 (12)N1—N2—C13117.73 (10)
C11—C10—C9121.39 (13)C5—O2—C3119.03 (12)
C11—C10—H10119.3
C8—C4—C5—O2178.51 (15)C4—C5—C11—C101.2 (2)
C1—C4—C5—O28.4 (4)C8—C9—C12—O3159.80 (15)
C1'—C4—C5—O2−14.6 (4)C10—C9—C12—O3−17.1 (2)
C8—C4—C5—C11−0.8 (2)C8—C9—C12—N1−20.8 (2)
C1—C4—C5—C11−170.9 (4)C10—C9—C12—N1162.30 (13)
C1'—C4—C5—C11166.0 (4)O4—C17—C18—C19−134.18 (14)
C5—C4—C1—O1179.1 (7)N2—C17—C18—C1948.51 (19)
C8—C4—C1—O19.2 (9)O4—C17—C18—C2342.43 (18)
C1'—C4—C1—O1−85 (3)N2—C17—C18—C23−134.88 (13)
C5—C4—C1—C25.0 (7)C23—C18—C19—C201.9 (2)
C8—C4—C1—C2−164.9 (4)C17—C18—C19—C20178.41 (13)
C1'—C4—C1—C2101 (3)C18—C19—C20—C210.0 (2)
O2—C3—C2—C141.7 (5)C18—C19—C20—C24−179.00 (15)
C6'—C3—C2—C1−150.7 (6)C19—C20—C21—C22−1.9 (2)
C6—C3—C2—C1169.6 (5)C24—C20—C21—C22177.18 (17)
C2'—C3—C2—C1−61.8 (5)C20—C21—C22—C231.7 (2)
C7—C3—C2—C1−66.8 (5)C20—C21—C22—C25−177.15 (17)
C7'—C3—C2—C1122.4 (5)C21—C22—C23—C180.4 (2)
O1—C1—C2—C3156.6 (8)C25—C22—C23—C18179.19 (16)
C4—C1—C2—C3−29.6 (7)C19—C18—C23—C22−2.1 (2)
C5—C4—C1'—O1'177.5 (8)C17—C18—C23—C22−178.97 (13)
C8—C4—C1'—O1'−15.7 (11)O3—C12—N1—N2−11.2 (2)
C1—C4—C1'—O1'82 (3)C9—C12—N1—N2169.32 (11)
C5—C4—C1'—C2'−3.3 (8)O4—C17—N2—N1−175.61 (12)
C8—C4—C1'—C2'163.5 (4)C18—C17—N2—N11.66 (18)
C1—C4—C1'—C2'−99 (3)O4—C17—N2—C13−5.3 (2)
O1'—C1'—C2'—C3−151.4 (8)C18—C17—N2—C13171.97 (12)
C4—C1'—C2'—C329.4 (8)C12—N1—N2—C1784.40 (16)
C2—C3—C2'—C1'61.4 (5)C12—N1—N2—C13−86.37 (16)
O2—C3—C2'—C1'−41.0 (6)C15—C13—N2—C1761.36 (17)
C6'—C3—C2'—C1'−176.2 (6)C16—C13—N2—C17−61.21 (18)
C6—C3—C2'—C1'148.0 (6)C14—C13—N2—C17179.54 (14)
C7—C3—C2'—C1'−123.8 (6)C15—C13—N2—N1−128.22 (13)
C7'—C3—C2'—C1'65.1 (6)C16—C13—N2—N1109.21 (14)
C5—C4—C8—C90.1 (2)C14—C13—N2—N1−10.03 (19)
C1—C4—C8—C9170.0 (4)C11—C5—O2—C3−177.56 (14)
C1'—C4—C8—C9−166.8 (4)C4—C5—O2—C33.1 (2)
C4—C8—C9—C100.3 (2)C2—C3—O2—C5−28.9 (3)
C4—C8—C9—C12−176.65 (14)C6'—C3—O2—C5161.4 (4)
C8—C9—C10—C110.1 (2)C6—C3—O2—C5−160.9 (3)
C12—C9—C10—C11177.22 (13)C2'—C3—O2—C525.7 (3)
C9—C10—C11—C5−0.9 (2)C7—C3—O2—C588.4 (2)
O2—C5—C11—C10−178.14 (14)C7'—C3—O2—C5−85.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16C···O40.962.393.007 (2)121
C15—H15A···O40.962.362.918 (2)117
C8—H8···O4i0.932.483.3214 (18)151
N1—H1···O4i0.862 (17)2.096 (18)2.9442 (15)167.8 (15)
Symmetry code: (i) −x+3/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formulaC25H30N2O4
Mr422.51
Crystal system, space groupMonoclinic, P21/n
Temperature (K)297
a, b, c (Å)14.1260 (12), 10.6964 (9), 15.4370 (13)
β (°) 96.426 (2)
V (Å3)2317.8 (3)
Z4
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2005)
Tmin, Tmax0.976, 0.984
No. of measured, independent and
observed [I > 2σ(I)] reflections		13199, 5043, 3983
Rint0.020
(sin θ/λ)max (Å−1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.142, 1.04
No. of reflections5043
No. of parameters338
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.22, −0.17

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16C···O40.962.393.007 (2)121
C15—H15A···O40.962.362.918 (2)117
C8—H8···O4i0.932.483.3214 (18)151
N1—H1···O4i0.862 (17)2.096 (18)2.9442 (15)167.8 (15)
Symmetry code: (i) −x+3/2, y+1/2, −z+1/2.
 

Acknowledgements

The authors acknowledge financial support from the Science Foundation of the Southern Medical University for New Excellent Talents (No. B1000374).

References

First citationBruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationMao, C. H., Wang, K. L., Wang, Z. M., Qu, X., Huang, R. & Wang, Q. M. (2008). Bioorg. Med. Chem. 16, 488–494.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationSawada, Y., Yanai, T., Nakagawa, H., Kajino, F., Tsukamoto, Y., Yokoi, S., Yanagi, M., Sugizaki, H., Toya, T. & Masui, A. (2003). Pest Manag. Sci. 59, 49–57.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationSheldrick, G. M. (2005). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationZhao, P.-L., Huang, W. & Yang, G.-F. (2005). Acta Cryst. E61, o2139–o2141.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationZhao, P. L., Li, J. & Yang, G. F. (2007). Bioorg. Med. Chem. 15, 1888–1895.  Web of Science CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 8| August 2009| Page o2015
doi:10.1107/S1600536809028815
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