organic compounds
3-Mesityl-2-oxo-1-oxaspiro[4.4]non-3-en-4-yl 4-chlorobenzoate
aInstitute of Science, Zhejiang Sci_tec University, Hangzhou 310032, People's Republic of China, and bCollege of Agriculture and Biotechnology, Zhejiang University, Hangzhou 310029, People's Republic of China
*Correspondence e-mail: jinhaozhao@zju.edu.cn
The title compound, C24H23ClO4, is a potent insecticide and miticide. The five-membered cyclopentane ring displays an with the atom at the flap position 0.611 (2) Å out of the mean plane formed by the other four atoms. The furan ring makes dihedral angles of 71.3 (2) and 81.9 (2)°, respectively, with the 2,4,6-trimethylphenyl and 4-chlorophenyl rings. The dihedral angle between the two benzene rings is 76.6 (1)°. In the crystal, molecules are linked through weak intermolecular C—H⋯O hydrogen bonds, forming chains running along the c axis.
Related literature
For a related insecticide, see: Bayer, (1995). For a related methylbutyrate structure, see: Yu et al. (2009). For the extinction correction, see: Larson (1970).
Experimental
Crystal data
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Refinement
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Data collection: PROCESS-AUTO (Rigaku, 1998); cell PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1993); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.
Supporting information
10.1107/S1600536809006503/si2154sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809006503/si2154Isup2.hkl
4-hydroxyl-3-(2,4,6-trimethylphenyl)-1-oxaspiro[4,4]non-3-en-2-one (0.272 g, 1 mmol) and triethylamine (0.152 g, 1.5 mmol) were dissolved in dry dichloromethane (15 ml) with stirring. 4-chlorophenylacetyl chloride (0.210 g, 1.2 mmol) was added dropwise to the mixture in a water bath. The mixture was stirred at 293–298 K for 5 h, and then 1% aqueous HCl was added. The organic layer was washed to neutral with water and dried via Na2SO4. After filtered and concentrated, the organic residue was purified by silica gel
eluted with ethyl acetate-petroleum ether (1:3. v/v) to give a white solid (yield 81%, 0.334 g), which was then recrystallized from acetone/ethanol (1:2, v/v) to give colourless blocks.The H atoms were geometrically placed (C—H = 0.93–0.98 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). The methyl group was allowed to rotate, but not to tip, to best fit the electron density.
Data collection: PROCESS-AUTO (Rigaku, 1998); cell
PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1993); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004).C24H23ClO4 | F(000) = 864.00 |
Mr = 410.90 | Dx = 1.254 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71075 Å |
Hall symbol: -P 2ybc | Cell parameters from 20338 reflections |
a = 6.4880 (2) Å | θ = 3.0–27.4° |
b = 22.9397 (8) Å | µ = 0.20 mm−1 |
c = 14.6305 (6) Å | T = 296 K |
β = 91.533 (1)° | Block, colorless |
V = 2176.72 (14) Å3 | 0.62 × 0.48 × 0.34 mm |
Z = 4 |
Rigaku R-AXIS RAPID diffractometer | 3235 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.030 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −8→7 |
Tmin = 0.867, Tmax = 0.934 | k = −29→29 |
33470 measured reflections | l = −18→18 |
4926 independent reflections |
Refinement on F2 | w = 1/[0.0002Fo2 + 1.45σ(Fo2)]/(4Fo2) |
R[F2 > 2σ(F2)] = 0.037 | (Δ/σ)max < 0.001 |
wR(F2) = 0.092 | Δρmax = 0.14 e Å−3 |
S = 1.00 | Δρmin = −0.17 e Å−3 |
4926 reflections | Extinction correction: Larson (1970), equation 22 |
263 parameters | Extinction coefficient: 695 (30) |
H-atom parameters constrained |
C24H23ClO4 | V = 2176.72 (14) Å3 |
Mr = 410.90 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 6.4880 (2) Å | µ = 0.20 mm−1 |
b = 22.9397 (8) Å | T = 296 K |
c = 14.6305 (6) Å | 0.62 × 0.48 × 0.34 mm |
β = 91.533 (1)° |
Rigaku R-AXIS RAPID diffractometer | 4926 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 3235 reflections with F2 > 2σ(F2) |
Tmin = 0.867, Tmax = 0.934 | Rint = 0.030 |
33470 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 263 parameters |
wR(F2) = 0.092 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.14 e Å−3 |
4926 reflections | Δρmin = −0.17 e Å−3 |
Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.25024 (8) | 0.45321 (2) | −0.01486 (4) | 0.0960 (2) | |
O1 | 0.83337 (16) | 0.19253 (4) | 0.49303 (8) | 0.0589 (3) | |
O2 | 0.83728 (17) | 0.23623 (5) | 0.62950 (8) | 0.0671 (3) | |
O3 | 0.64511 (14) | 0.29954 (4) | 0.33174 (6) | 0.0563 (3) | |
O4 | 0.31480 (18) | 0.29640 (6) | 0.37120 (10) | 0.0822 (5) | |
C1 | 0.7983 (2) | 0.23874 (6) | 0.54880 (12) | 0.0531 (5) | |
C2 | 0.7122 (2) | 0.28760 (6) | 0.49455 (12) | 0.0493 (4) | |
C3 | 0.6530 (2) | 0.34424 (6) | 0.53503 (11) | 0.0517 (4) | |
C4 | 0.4814 (2) | 0.34712 (6) | 0.59006 (12) | 0.0617 (5) | |
C5 | 0.4308 (3) | 0.40037 (8) | 0.62872 (12) | 0.0815 (7) | |
C6 | 0.5482 (4) | 0.45001 (8) | 0.61565 (16) | 0.0906 (8) | |
C7 | 0.7148 (3) | 0.44552 (8) | 0.56064 (17) | 0.0903 (7) | |
C8 | 0.7716 (2) | 0.39386 (6) | 0.51955 (12) | 0.0664 (5) | |
C9 | 0.3514 (2) | 0.29404 (8) | 0.60759 (14) | 0.0839 (7) | |
C10 | 0.4933 (4) | 0.50730 (9) | 0.66180 (18) | 0.1028 (11) | |
C11 | 0.9564 (2) | 0.39222 (8) | 0.45970 (17) | 0.0990 (8) | |
C12 | 0.7031 (2) | 0.26889 (6) | 0.40947 (12) | 0.0498 (4) | |
C13 | 0.4412 (2) | 0.31350 (6) | 0.31964 (12) | 0.0546 (5) | |
C14 | 0.4018 (2) | 0.34881 (6) | 0.23706 (11) | 0.0479 (4) | |
C15 | 0.5560 (2) | 0.37213 (6) | 0.18689 (12) | 0.0557 (5) | |
C16 | 0.5109 (2) | 0.40460 (6) | 0.10976 (12) | 0.0653 (5) | |
C17 | 0.3095 (2) | 0.41340 (6) | 0.08306 (12) | 0.0599 (5) | |
C18 | 0.1545 (2) | 0.38918 (8) | 0.13064 (14) | 0.0864 (7) | |
C19 | 0.1998 (2) | 0.35689 (8) | 0.20804 (14) | 0.0813 (6) | |
C20 | 0.7718 (2) | 0.20699 (6) | 0.39878 (11) | 0.0526 (4) | |
C21 | 0.6061 (2) | 0.16400 (6) | 0.36752 (12) | 0.0650 (5) | |
C22 | 0.7311 (3) | 0.10964 (6) | 0.34622 (13) | 0.0819 (6) | |
C23 | 0.9180 (3) | 0.13309 (9) | 0.29939 (14) | 0.0926 (7) | |
C24 | 0.9516 (2) | 0.19490 (6) | 0.33625 (12) | 0.0718 (6) | |
H5 | 0.3147 | 0.4028 | 0.6644 | 0.098* | |
H7 | 0.7933 | 0.4787 | 0.5504 | 0.108* | |
H15 | 0.6928 | 0.3660 | 0.2050 | 0.067* | |
H16 | 0.6166 | 0.4205 | 0.0760 | 0.078* | |
H18 | 0.0182 | 0.3944 | 0.1111 | 0.104* | |
H19 | 0.0936 | 0.3405 | 0.2409 | 0.098* | |
H91 | 0.2999 | 0.2786 | 0.5504 | 0.101* | |
H92 | 0.2377 | 0.3047 | 0.6448 | 0.101* | |
H93 | 0.4337 | 0.2650 | 0.6387 | 0.101* | |
H101 | 0.3526 | 0.5060 | 0.6804 | 0.123* | |
H102 | 0.5823 | 0.5131 | 0.7145 | 0.123* | |
H103 | 0.5104 | 0.5389 | 0.6196 | 0.123* | |
H111 | 1.0216 | 0.3547 | 0.4648 | 0.119* | |
H112 | 0.9133 | 0.3989 | 0.3973 | 0.119* | |
H113 | 1.0523 | 0.4220 | 0.4788 | 0.119* | |
H211 | 0.5096 | 0.1565 | 0.4156 | 0.078* | |
H212 | 0.5318 | 0.1781 | 0.3135 | 0.078* | |
H221 | 0.7709 | 0.0891 | 0.4019 | 0.098* | |
H222 | 0.6533 | 0.0836 | 0.3060 | 0.098* | |
H231 | 1.0375 | 0.1090 | 0.3136 | 0.111* | |
H232 | 0.8938 | 0.1340 | 0.2337 | 0.111* | |
H241 | 1.0814 | 0.1973 | 0.3705 | 0.086* | |
H242 | 0.9517 | 0.2227 | 0.2863 | 0.086* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.1083 (4) | 0.0976 (3) | 0.0808 (4) | 0.0141 (2) | −0.0245 (3) | 0.0319 (3) |
O1 | 0.0795 (7) | 0.0537 (6) | 0.0429 (7) | 0.0070 (5) | −0.0072 (5) | 0.0039 (5) |
O2 | 0.0907 (8) | 0.0672 (7) | 0.0425 (8) | −0.0056 (5) | −0.0117 (6) | 0.0056 (6) |
O3 | 0.0610 (6) | 0.0657 (6) | 0.0422 (7) | 0.0093 (5) | 0.0000 (5) | 0.0114 (5) |
O4 | 0.0608 (7) | 0.1034 (11) | 0.0823 (11) | −0.0012 (7) | 0.0019 (7) | 0.0253 (9) |
C1 | 0.0638 (10) | 0.0529 (9) | 0.0423 (11) | −0.0086 (7) | −0.0043 (8) | 0.0043 (8) |
C2 | 0.0584 (9) | 0.0474 (8) | 0.0419 (10) | −0.0054 (6) | −0.0011 (7) | 0.0040 (7) |
C3 | 0.0668 (10) | 0.0462 (8) | 0.0417 (10) | −0.0040 (7) | −0.0053 (8) | 0.0022 (7) |
C4 | 0.0803 (11) | 0.0605 (10) | 0.0442 (11) | 0.0015 (8) | −0.0008 (9) | −0.0006 (8) |
C5 | 0.1075 (15) | 0.0836 (13) | 0.0534 (13) | 0.0250 (11) | 0.0025 (11) | −0.0061 (11) |
C6 | 0.152 (2) | 0.0569 (12) | 0.0618 (15) | 0.0231 (13) | −0.0212 (14) | −0.0090 (10) |
C7 | 0.1344 (19) | 0.0487 (10) | 0.0867 (17) | −0.0122 (11) | −0.0215 (14) | 0.0013 (11) |
C8 | 0.0826 (12) | 0.0518 (10) | 0.0642 (13) | −0.0084 (8) | −0.0087 (10) | 0.0072 (9) |
C9 | 0.0858 (13) | 0.0926 (13) | 0.0745 (15) | −0.0107 (10) | 0.0220 (11) | 0.0034 (11) |
C10 | 0.132 (3) | 0.0769 (14) | 0.098 (2) | 0.0380 (17) | −0.026 (2) | −0.0258 (14) |
C11 | 0.0945 (15) | 0.0814 (13) | 0.121 (2) | −0.0267 (10) | 0.0057 (14) | 0.0203 (13) |
C12 | 0.0559 (9) | 0.0510 (8) | 0.0424 (10) | −0.0014 (6) | −0.0027 (7) | 0.0088 (8) |
C13 | 0.0541 (9) | 0.0598 (9) | 0.0496 (11) | −0.0062 (7) | −0.0040 (8) | 0.0024 (8) |
C14 | 0.0525 (9) | 0.0445 (8) | 0.0464 (10) | −0.0003 (6) | −0.0049 (7) | −0.0009 (7) |
C15 | 0.0525 (9) | 0.0602 (9) | 0.0544 (11) | 0.0090 (7) | −0.0011 (8) | 0.0079 (8) |
C16 | 0.0638 (11) | 0.0705 (10) | 0.0619 (12) | 0.0078 (8) | 0.0060 (9) | 0.0169 (9) |
C17 | 0.0697 (11) | 0.0565 (9) | 0.0527 (11) | 0.0068 (8) | −0.0113 (9) | 0.0048 (8) |
C18 | 0.0590 (11) | 0.1087 (15) | 0.0901 (16) | −0.0019 (10) | −0.0229 (11) | 0.0293 (13) |
C19 | 0.0559 (11) | 0.1068 (14) | 0.0806 (15) | −0.0106 (9) | −0.0092 (10) | 0.0308 (12) |
C20 | 0.0637 (9) | 0.0546 (9) | 0.0392 (10) | 0.0039 (7) | −0.0034 (8) | 0.0036 (7) |
C21 | 0.0785 (11) | 0.0597 (9) | 0.0562 (12) | −0.0025 (8) | −0.0077 (9) | −0.0014 (8) |
C22 | 0.1206 (16) | 0.0589 (11) | 0.0655 (14) | 0.0083 (10) | −0.0084 (12) | −0.0098 (10) |
C23 | 0.1229 (17) | 0.0889 (13) | 0.0664 (15) | 0.0319 (12) | 0.0108 (13) | −0.0087 (11) |
C24 | 0.0745 (11) | 0.0834 (12) | 0.0579 (13) | 0.0147 (9) | 0.0083 (10) | 0.0063 (10) |
Cl1—C17 | 1.7334 (17) | C20—C24 | 1.527 (2) |
O1—C1 | 1.361 (2) | C21—C22 | 1.524 (2) |
O1—C20 | 1.4633 (19) | C22—C23 | 1.508 (3) |
O2—C1 | 1.202 (2) | C23—C24 | 1.530 (2) |
O3—C12 | 1.3807 (19) | C5—H5 | 0.930 |
O3—C13 | 1.3681 (18) | C7—H7 | 0.930 |
O4—C13 | 1.195 (2) | C9—H91 | 0.960 |
C1—C2 | 1.475 (2) | C9—H92 | 0.960 |
C2—C3 | 1.483 (2) | C9—H93 | 0.960 |
C2—C12 | 1.317 (2) | C10—H101 | 0.960 |
C3—C4 | 1.393 (2) | C10—H102 | 0.960 |
C3—C8 | 1.396 (2) | C10—H103 | 0.960 |
C4—C5 | 1.389 (2) | C11—H111 | 0.960 |
C4—C9 | 1.507 (2) | C11—H112 | 0.960 |
C5—C6 | 1.386 (2) | C11—H113 | 0.960 |
C6—C7 | 1.369 (3) | C15—H15 | 0.930 |
C6—C10 | 1.524 (3) | C16—H16 | 0.930 |
C7—C8 | 1.383 (2) | C18—H18 | 0.930 |
C8—C11 | 1.504 (2) | C19—H19 | 0.930 |
C12—C20 | 1.4978 (19) | C21—H211 | 0.970 |
C13—C14 | 1.471 (2) | C21—H212 | 0.970 |
C14—C15 | 1.366 (2) | C22—H221 | 0.970 |
C14—C19 | 1.380 (2) | C22—H222 | 0.970 |
C15—C16 | 1.377 (2) | C23—H231 | 0.970 |
C16—C17 | 1.368 (2) | C23—H232 | 0.970 |
C17—C18 | 1.357 (2) | C24—H241 | 0.970 |
C18—C19 | 1.378 (2) | C24—H242 | 0.970 |
C20—C21 | 1.520 (2) | ||
C1—O1—C20 | 110.04 (11) | C6—C5—H5 | 119.0 |
C12—O3—C13 | 117.84 (11) | C6—C7—H7 | 118.5 |
O1—C1—O2 | 121.16 (14) | C8—C7—H7 | 118.5 |
O1—C1—C2 | 109.66 (14) | C4—C9—H91 | 109.5 |
O2—C1—C2 | 129.18 (15) | C4—C9—H92 | 109.5 |
C1—C2—C3 | 123.33 (15) | C4—C9—H93 | 109.5 |
C1—C2—C12 | 105.54 (13) | H91—C9—H92 | 109.5 |
C3—C2—C12 | 131.13 (14) | H91—C9—H93 | 109.5 |
C2—C3—C4 | 119.47 (13) | H92—C9—H93 | 109.5 |
C2—C3—C8 | 119.99 (14) | C6—C10—H101 | 109.5 |
C4—C3—C8 | 120.52 (14) | C6—C10—H102 | 109.5 |
C3—C4—C5 | 118.58 (15) | C6—C10—H103 | 109.5 |
C3—C4—C9 | 121.32 (14) | H101—C10—H102 | 109.5 |
C5—C4—C9 | 120.11 (16) | H101—C10—H103 | 109.5 |
C4—C5—C6 | 121.98 (19) | H102—C10—H103 | 109.5 |
C5—C6—C7 | 117.69 (18) | C8—C11—H111 | 109.5 |
C5—C6—C10 | 120.8 (2) | C8—C11—H112 | 109.5 |
C7—C6—C10 | 121.5 (2) | C8—C11—H113 | 109.5 |
C6—C7—C8 | 122.96 (18) | H111—C11—H112 | 109.5 |
C3—C8—C7 | 118.25 (17) | H111—C11—H113 | 109.5 |
C3—C8—C11 | 121.71 (15) | H112—C11—H113 | 109.5 |
C7—C8—C11 | 120.04 (16) | C14—C15—H15 | 119.7 |
O3—C12—C2 | 128.10 (12) | C16—C15—H15 | 119.7 |
O3—C12—C20 | 118.17 (13) | C15—C16—H16 | 120.2 |
C2—C12—C20 | 113.69 (13) | C17—C16—H16 | 120.2 |
O3—C13—O4 | 121.26 (15) | C17—C18—H18 | 120.1 |
O3—C13—C14 | 112.40 (13) | C19—C18—H18 | 120.1 |
O4—C13—C14 | 126.30 (15) | C14—C19—H19 | 119.8 |
C13—C14—C15 | 122.92 (13) | C18—C19—H19 | 119.8 |
C13—C14—C19 | 117.99 (14) | C20—C21—H211 | 111.2 |
C15—C14—C19 | 119.05 (15) | C20—C21—H212 | 111.2 |
C14—C15—C16 | 120.62 (14) | C22—C21—H211 | 111.2 |
C15—C16—C17 | 119.63 (15) | C22—C21—H212 | 111.2 |
Cl1—C17—C16 | 120.17 (13) | H211—C21—H212 | 109.5 |
Cl1—C17—C18 | 119.25 (13) | C21—C22—H221 | 110.9 |
C16—C17—C18 | 120.53 (16) | C21—C22—H222 | 110.9 |
C17—C18—C19 | 119.79 (16) | C23—C22—H221 | 110.9 |
C14—C19—C18 | 120.34 (16) | C23—C22—H222 | 110.9 |
O1—C20—C12 | 101.01 (11) | H221—C22—H222 | 109.5 |
O1—C20—C21 | 108.02 (12) | C22—C23—H231 | 110.3 |
O1—C20—C24 | 109.27 (12) | C22—C23—H232 | 110.3 |
C12—C20—C21 | 115.86 (12) | C24—C23—H231 | 110.3 |
C12—C20—C24 | 117.98 (12) | C24—C23—H232 | 110.3 |
C21—C20—C24 | 104.32 (12) | H231—C23—H232 | 109.5 |
C20—C21—C22 | 102.49 (13) | C20—C24—H241 | 110.3 |
C21—C22—C23 | 103.88 (14) | C20—C24—H242 | 110.3 |
C22—C23—C24 | 106.19 (16) | C23—C24—H241 | 110.3 |
C20—C24—C23 | 106.01 (14) | C23—C24—H242 | 110.3 |
C4—C5—H5 | 119.0 | H241—C24—H242 | 109.5 |
C1—O1—C20—C12 | 1.70 (14) | C5—C6—C7—C8 | −1.2 (3) |
C1—O1—C20—C21 | −120.35 (12) | C10—C6—C7—C8 | 178.4 (2) |
C1—O1—C20—C24 | 126.75 (12) | C6—C7—C8—C3 | 0.1 (2) |
C20—O1—C1—O2 | 179.74 (14) | C6—C7—C8—C11 | 179.8 (2) |
C20—O1—C1—C2 | −0.57 (16) | O3—C12—C20—O1 | 175.69 (11) |
C12—O3—C13—O4 | −5.0 (2) | O3—C12—C20—C21 | −67.91 (18) |
C12—O3—C13—C14 | 176.84 (12) | O3—C12—C20—C24 | 56.74 (18) |
C13—O3—C12—C2 | −71.27 (19) | C2—C12—C20—O1 | −2.47 (16) |
C13—O3—C12—C20 | 110.86 (14) | C2—C12—C20—C21 | 113.92 (16) |
O1—C1—C2—C3 | 178.86 (12) | C2—C12—C20—C24 | −121.43 (16) |
O1—C1—C2—C12 | −1.01 (16) | O3—C13—C14—C15 | −9.4 (2) |
O2—C1—C2—C3 | −1.5 (2) | O3—C13—C14—C19 | 168.51 (14) |
O2—C1—C2—C12 | 178.65 (16) | O4—C13—C14—C15 | 172.61 (16) |
C1—C2—C3—C4 | −70.0 (2) | O4—C13—C14—C19 | −9.5 (2) |
C1—C2—C3—C8 | 108.53 (18) | C13—C14—C15—C16 | 179.61 (14) |
C1—C2—C12—O3 | −175.75 (13) | C13—C14—C19—C18 | −179.44 (16) |
C1—C2—C12—C20 | 2.20 (17) | C15—C14—C19—C18 | −1.5 (2) |
C3—C2—C12—O3 | 4.4 (2) | C19—C14—C15—C16 | 1.7 (2) |
C3—C2—C12—C20 | −177.65 (14) | C14—C15—C16—C17 | −0.2 (2) |
C12—C2—C3—C4 | 109.8 (2) | C15—C16—C17—Cl1 | −178.99 (12) |
C12—C2—C3—C8 | −71.6 (2) | C15—C16—C17—C18 | −1.7 (2) |
C2—C3—C4—C5 | 178.81 (15) | Cl1—C17—C18—C19 | 179.29 (14) |
C2—C3—C4—C9 | −1.5 (2) | C16—C17—C18—C19 | 1.9 (2) |
C2—C3—C8—C7 | −178.18 (17) | C17—C18—C19—C14 | −0.4 (2) |
C2—C3—C8—C11 | 2.1 (2) | O1—C20—C21—C22 | −78.01 (15) |
C4—C3—C8—C7 | 0.4 (2) | O1—C20—C24—C23 | 94.02 (15) |
C4—C3—C8—C11 | −179.37 (17) | C12—C20—C21—C22 | 169.61 (14) |
C8—C3—C4—C5 | 0.3 (2) | C12—C20—C24—C23 | −151.47 (14) |
C8—C3—C4—C9 | 179.99 (14) | C21—C20—C24—C23 | −21.28 (17) |
C3—C4—C5—C6 | −1.4 (2) | C24—C20—C21—C22 | 38.17 (16) |
C9—C4—C5—C6 | 178.88 (19) | C20—C21—C22—C23 | −40.81 (18) |
C4—C5—C6—C7 | 1.8 (3) | C21—C22—C23—C24 | 27.7 (2) |
C4—C5—C6—C10 | −177.7 (2) | C22—C23—C24—C20 | −4.02 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
C24—H242···O2i | 0.97 | 2.57 | 3.475 (2) | 155 |
Symmetry code: (i) x, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C24H23ClO4 |
Mr | 410.90 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 6.4880 (2), 22.9397 (8), 14.6305 (6) |
β (°) | 91.533 (1) |
V (Å3) | 2176.72 (14) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.20 |
Crystal size (mm) | 0.62 × 0.48 × 0.34 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.867, 0.934 |
No. of measured, independent and observed [F2 > 2σ(F2)] reflections | 33470, 4926, 3235 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.092, 1.00 |
No. of reflections | 4926 |
No. of parameters | 263 |
No. of restraints | ? |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.14, −0.17 |
Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SIR97 (Altomare et al., 1993), CRYSTALS (Betteridge et al., 2003), ORTEP-3 for Windows (Farrugia, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
C24—H242···O2i | 0.97 | 2.57 | 3.475 (2) | 155 |
Symmetry code: (i) x, −y+1/2, z−1/2. |
Acknowledgements
The authors are grateful for support from the National Natural Science Foundation of China (No. 30700532) and the Science and Technology Project of Zhejiang Province (No. 2008C02007-3, 2008C21029). They also thank Professor Jian-Ming Gu for help with the analysis of the crystal data.
References
Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350. CrossRef Web of Science IUCr Journals Google Scholar
Bayer Aktiengesellschaft. (1995). WO patent No. 9 504 719A1. Google Scholar
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Larson, A. C. (1970). Crystallographic Computing, edited by F. R. Ahmed, S. R. Hall & C. P. Huber, pp. 291–294. Copenhagen: Munksgaard. Google Scholar
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4-hydroxyl-3-(2,4,6-trimethylphenyl)-1-oxaspiro[4,4]non-3-en-2-one (HTPO) is a key intermediate of Spiromesifen, which is an efficient insecticide and miticide, developed by Bayer company (Bayer, 1995). As part of our continuing interest in the design and synthesis of the new insecticide and miticide, we have isolated the title compound (Fig. 1), by the condensation reaction of 4-chlorophenyl- acetylchloride and HTPO as colorless crystals. The molecule contains two six-membered rings and two five-membered rings. Atoms C1, C2, C12, C20, O1 and O2 are coplanar, the largest deviation being 0.011 (11) Å for O1. As expected, C2=C12, C1=O2 and C13=O4 are typical double bonds with bond distances of 1.317 (2), 1.202 (2) and 1.195 (3) Å suggests that C2, C12 and C13 atoms are sp2 hybridized. The bond distance of C1—C2 is 1.475 (2) Å, suggesting that the carbonyl group on C1 has formed a conjugate system with double bond on C2 and C12. In the crystal, molecules are linked through weak intermolecular C—H···O hydrogen bonds (Table 1), forming chains running along the c axis (Fig. 2), in contrast to the related 3-mesityl-2-oxo-1-oxaspiro[4.4]non-3-en-4-yl 2-(chlorophenyl)-3-methyl- butyrate structure, where intermolecular C—H···Cl hydrogen bonds forming chains along the screw axis direction b (Yu et al. 2009).