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ISSN: 2056-9890

9-(2,4-Di­chloro­phen­yl)-3,3,6,6-tetra­methyl-3,4,5,6-tetra­hydro-9H-xanthene-1,8(2H,7H)-dione

aThe College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
*Correspondence e-mail: shihao@zjut.edu.cn

(Received 7 November 2010; accepted 11 November 2010; online 17 November 2010)

The title compound, C23H24Cl2O3, was synthesized by reaction of 2,4-dichloro­benzaldehyde and 5,5-dimethyl­cyclo­hexane-1,3-dione in ethyl­ene glycol. The central ring of the xanthene moiety is almost planar (with an r.m.s. deviation of 0.0268 Å from the least-squares plane) while the two outer rings, in a cis arrangement, display envelope conformations. The ring of the 2,4-dichloro­phenyl substituent is nearly perpendicular [85.89 (4)°] to the xanthene ring system.

Related literature

For related structures, see: Odabaşoğlu et al. (2008[Odabaşoğlu, M., Kaya, M., Yıldırır, Y. & Büyükgüngör, O. (2008). Acta Cryst. E64, o681.]); Bigdeli et al. (2007[Bigdeli, M. A., Mahdavinia, G. H. & Amani, V. (2007). Acta Cryst. E63, o3493.]); Tu et al. (2002[Tu, S., Zhou, J., Lu, Z., Deng, X., Shi, D. & Wang, S. (2002). Synth. Commun. 32, 3063-3067.], 2004[Tu, S. J., Miao, C. B., Fang, F. & Jiang, H. (2004). Jiegou Huaxue, 23, 187-191.]); Jeyakanthan et al. (1999[Jeyakanthan, J., Shanmuga Sundara Raj, S., Velmurugan, D., Fun, H.-K. & Murugan, P. (1999). Acta Cryst. C55, 1515-1517.]); Li et al. (2005[Li, T. J., Tu, S. J., Zhu, S. L. & Zhang, X. J. (2005). Jiegou Huaxue, 24, 25-29.]); Shi et al. (1997[Shi, D. Q., Mu, L. L., Lu, Z. S., Gao, Y. G. & Dai, G. Y. (1997). Jiegou Huaxue, 16, 484-487.]). For applications of xanthene derivatives, see: Poupelin et al. (1978[Poupelin, J. P., Saint-Rut, G., Foussard-Blanpin, O., Narcisse, G., Uchida- Ernouf, G. & Lacroix, R. (1978). Eur. J. Med. Chem. 13, 67-71.]); Lambert et al. (1997[Lambert, R. W., Martin, J. A., Merrett, J. H., Parkes, K. E. B. & Thomas, G. J. (1997). PCT Int. Appl. WO 9 706 178.]); Menchen et al. (2003[Menchen, S. M., Benson, S. C., Lam, J. Y. L., Zhen, W., Sun, D., Rosenblum, B. B., Khan, S. H. & Taing, M. (2003). US Patent 6 583 168.]); Banerjee & Mukherjee (1981[Banerjee, A. & Mukherjee, A. K. (1981). Stain Technol. 56, 83-85.]). For ring puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C23H24Cl2O3

  • Mr = 419.32

  • Monoclinic, P 21 /c

  • a = 9.8154 (10) Å

  • b = 19.833 (2) Å

  • c = 11.4441 (11) Å

  • β = 111.873 (2)°

  • V = 2067.4 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.34 mm−1

  • T = 296 K

  • 0.20 × 0.10 × 0.10 mm

Data collection
  • Bruker APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1997[Bruker (1997). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.936, Tmax = 0.967

  • 13137 measured reflections

  • 4961 independent reflections

  • 3331 reflections with I > 2σ(I)

  • Rint = 0.027

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.124

  • S = 1.02

  • 4961 reflections

  • 257 parameters

  • H-atom parameters constrained

  • Δρmax = 0.36 e Å−3

  • Δρmin = −0.55 e Å−3

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART, SAINT and SADABS. 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Comment top

Xanthene-based compounds are biological importance and useful in drug discovery, such as anti-inflammatory effect (Poupelin et al., 1978) and antiviral activity (Lambert et al., 1997). Xanthenes are also an important class of organic compounds that find uses as dyes and fluorescent materials for visualization of bio-molecules and laser technologies due to their useful spectroscopic properties (Menchen et al., 2003; Banerjee & Mukherjee, 1981). In view of the importance of the title compound, herein its crystal structure is reported.

The bond lengths and angles in the title molecule (Fig. 1) are comparable with those reported for related structures (Odabaşoğlu et al., 2008; Bigdeli et al., 2007; Tu et al., 2002; Jeyakanthan et al., 1999; Li et al., 2005; Shi et al., 1997; Tu et al., 2004). The central pyran ring of the xanthene moiety is planar, and the two outer rings (ring A (C1—C4/C11/C10) and ring C (C5–C8/C13/C12)) are in envelope conformations, ring A with puckering parameters (Cremer & Pople, 1975) Q= 0.4511 (22) Å, θ= 125.45 (27)°, φ = 297.4 (3)° and ring C with puckering parameters Q= 0.4807 (22) Å, θ= 56.96 (25)°, φ = 58.0 (3)°. Rings A and C are in a cis conformation, atoms C3 and C6 displaced by 0.6311 (28) and 0.6684 (28) Å from the plane of the other ring atoms, respectively. Ring D (C18—C23) is, of course, planar. The dihedral angle between the least-squares plane of the xanthene ring and the benzene ring is 85.89 (4)°.

Related literature top

For related structures, see: Odabaşoğlu et al. (2008); Bigdeli et al. (2007); Tu et al. (2002, 2004); Jeyakanthan et al. (1999); Li et al. (2005); Shi et al. (1997). For applications of xanthene derivatives, see: Poupelin et al. (1978); Lambert et al. (1997); Menchen et al. (2003); Banerjee & Mukherjee (1981). For ring puckering parameters, see: Cremer & Pople (1975).

Experimental top

A mixture of 2,4-dichlorobenzaldehyde (5 mmol), 5,5-dimethyl-1,3- cyclohexanedione (10 mmol) and 15 ml of ethylene glycol was transferred into a flask connected with refluxing equipment. After stirring at 80°C for 1.5 h, the reaction mixture was cooled to room temperature and poured into 150 ml water, the precipitated product was filtered and recrystallized with ethanol to give the title compound. Crystals suitable for X-ray structure analysis were obtained by slow evaporation from a solution of methanol at room temperature.

Refinement top

All H atoms were placed in geometrical positions and constrained to ride on their parent atoms with C–H distances in the range 0.93–0.97 Å, They were treated as riding atoms, with Uiso(H) = 1.5Ueq(C) for methyl H and 1.2Ueq(C) for other H atoms).

Structure description top

Xanthene-based compounds are biological importance and useful in drug discovery, such as anti-inflammatory effect (Poupelin et al., 1978) and antiviral activity (Lambert et al., 1997). Xanthenes are also an important class of organic compounds that find uses as dyes and fluorescent materials for visualization of bio-molecules and laser technologies due to their useful spectroscopic properties (Menchen et al., 2003; Banerjee & Mukherjee, 1981). In view of the importance of the title compound, herein its crystal structure is reported.

The bond lengths and angles in the title molecule (Fig. 1) are comparable with those reported for related structures (Odabaşoğlu et al., 2008; Bigdeli et al., 2007; Tu et al., 2002; Jeyakanthan et al., 1999; Li et al., 2005; Shi et al., 1997; Tu et al., 2004). The central pyran ring of the xanthene moiety is planar, and the two outer rings (ring A (C1—C4/C11/C10) and ring C (C5–C8/C13/C12)) are in envelope conformations, ring A with puckering parameters (Cremer & Pople, 1975) Q= 0.4511 (22) Å, θ= 125.45 (27)°, φ = 297.4 (3)° and ring C with puckering parameters Q= 0.4807 (22) Å, θ= 56.96 (25)°, φ = 58.0 (3)°. Rings A and C are in a cis conformation, atoms C3 and C6 displaced by 0.6311 (28) and 0.6684 (28) Å from the plane of the other ring atoms, respectively. Ring D (C18—C23) is, of course, planar. The dihedral angle between the least-squares plane of the xanthene ring and the benzene ring is 85.89 (4)°.

For related structures, see: Odabaşoğlu et al. (2008); Bigdeli et al. (2007); Tu et al. (2002, 2004); Jeyakanthan et al. (1999); Li et al. (2005); Shi et al. (1997). For applications of xanthene derivatives, see: Poupelin et al. (1978); Lambert et al. (1997); Menchen et al. (2003); Banerjee & Mukherjee (1981). For ring puckering parameters, see: Cremer & Pople (1975).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The preparation of the title compound.
[Figure 2] Fig. 2. Structure of the title compound, showing 30% probability displacement ellipsoids with atomic numbering scheme.
9-(2,4-Dichlorophenyl)-3,3,6,6-tetramethyl-3,4,5,6-tetrahydro-9H- xanthene-1,8(2H,7H)-dione top
Crystal data top
C23H24Cl2O3F(000) = 880
Mr = 419.32Dx = 1.347 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3489 reflections
a = 9.8154 (10) Åθ = 2.2–27.1°
b = 19.833 (2) ŵ = 0.34 mm1
c = 11.4441 (11) ÅT = 296 K
β = 111.873 (2)°Prism, colorless
V = 2067.4 (4) Å30.20 × 0.10 × 0.10 mm
Z = 4
Data collection top
Bruker APEX CCD
diffractometer
4961 independent reflections
Radiation source: fine-focus sealed tube3331 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ω scansθmax = 28.2°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 1311
Tmin = 0.936, Tmax = 0.967k = 2526
13137 measured reflectionsl = 1314
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0573P)2 + 0.4531P]
where P = (Fo2 + 2Fc2)/3
4961 reflections(Δ/σ)max < 0.001
257 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.55 e Å3
Crystal data top
C23H24Cl2O3V = 2067.4 (4) Å3
Mr = 419.32Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.8154 (10) ŵ = 0.34 mm1
b = 19.833 (2) ÅT = 296 K
c = 11.4441 (11) Å0.20 × 0.10 × 0.10 mm
β = 111.873 (2)°
Data collection top
Bruker APEX CCD
diffractometer
4961 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
3331 reflections with I > 2σ(I)
Tmin = 0.936, Tmax = 0.967Rint = 0.027
13137 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.124H-atom parameters constrained
S = 1.02Δρmax = 0.36 e Å3
4961 reflectionsΔρmin = 0.55 e Å3
257 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*/Ueq
Cl10.48123 (7)0.49352 (3)0.81227 (5)0.05835 (18)
Cl20.17633 (9)0.68975 (4)0.92235 (7)0.0867 (3)
O10.37359 (14)0.63325 (7)0.31501 (11)0.0429 (3)
O20.69826 (15)0.60451 (8)0.73455 (13)0.0535 (4)
O30.19747 (16)0.47392 (7)0.52949 (13)0.0495 (4)
C10.6678 (2)0.63036 (10)0.63116 (18)0.0396 (4)
C20.7753 (2)0.67506 (10)0.60270 (19)0.0437 (5)
H2A0.84110.64680.57850.052*
H2B0.83410.69860.67930.052*
C30.7073 (2)0.72708 (10)0.49949 (18)0.0399 (4)
C40.6005 (2)0.68988 (11)0.38461 (18)0.0447 (5)
H4A0.54260.72270.32330.054*
H4B0.65610.66370.34610.054*
C50.1471 (2)0.57908 (11)0.20690 (17)0.0450 (5)
H5A0.17010.54460.15690.054*
H5B0.12960.62090.15980.054*
C60.0085 (2)0.55903 (10)0.22869 (18)0.0409 (4)
C70.0469 (2)0.49772 (10)0.31638 (19)0.0426 (4)
H7A0.03650.48710.33900.051*
H7B0.06360.45940.27080.051*
C80.1799 (2)0.50728 (9)0.43512 (18)0.0369 (4)
C90.42019 (19)0.56963 (9)0.55622 (16)0.0336 (4)
H90.46990.52680.58810.040*
C100.52669 (18)0.61624 (9)0.52976 (16)0.0345 (4)
C110.50031 (19)0.64432 (9)0.41722 (17)0.0368 (4)
C120.27441 (19)0.58782 (9)0.32733 (17)0.0363 (4)
C130.29182 (19)0.55638 (9)0.43501 (17)0.0342 (4)
C140.0441 (2)0.61645 (11)0.2899 (2)0.0544 (6)
H14A0.02860.62560.37170.082*
H14B0.13460.60380.29800.082*
H14C0.05950.65610.23850.082*
C150.1116 (2)0.54084 (13)0.1031 (2)0.0561 (6)
H15A0.12380.57710.04440.084*
H15B0.20220.53350.11510.084*
H15C0.08450.50050.07070.084*
C160.6252 (2)0.78085 (11)0.5432 (2)0.0560 (6)
H16A0.58590.81400.47820.084*
H16B0.69170.80210.61810.084*
H16C0.54650.76010.56080.084*
C170.8269 (2)0.76069 (11)0.4648 (2)0.0512 (5)
H17A0.87680.72720.43510.077*
H17B0.89580.78260.53770.077*
H17C0.78330.79350.39980.077*
C180.36693 (19)0.59939 (9)0.65453 (16)0.0342 (4)
C190.3866 (2)0.56903 (10)0.76900 (17)0.0384 (4)
C200.3308 (2)0.59704 (11)0.85255 (18)0.0453 (5)
H200.34600.57630.92930.054*
C210.2526 (2)0.65597 (11)0.8201 (2)0.0492 (5)
C220.2324 (2)0.68823 (11)0.7101 (2)0.0521 (5)
H220.18100.72870.69030.063*
C230.2899 (2)0.65966 (10)0.62823 (19)0.0441 (5)
H230.27650.68160.55290.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0722 (4)0.0568 (3)0.0467 (3)0.0159 (3)0.0229 (3)0.0185 (2)
Cl20.1098 (6)0.0919 (5)0.0885 (5)0.0067 (4)0.0717 (5)0.0323 (4)
O10.0408 (7)0.0571 (8)0.0295 (7)0.0146 (6)0.0117 (6)0.0025 (6)
O20.0466 (8)0.0693 (10)0.0385 (8)0.0043 (7)0.0090 (6)0.0099 (7)
O30.0550 (8)0.0487 (8)0.0469 (9)0.0060 (7)0.0217 (7)0.0081 (7)
C10.0378 (10)0.0441 (11)0.0370 (10)0.0025 (8)0.0139 (8)0.0023 (8)
C20.0358 (10)0.0477 (11)0.0460 (12)0.0039 (8)0.0136 (9)0.0014 (9)
C30.0368 (9)0.0430 (10)0.0417 (11)0.0042 (8)0.0165 (8)0.0025 (8)
C40.0445 (11)0.0556 (12)0.0362 (10)0.0118 (9)0.0178 (9)0.0004 (9)
C50.0427 (11)0.0608 (13)0.0305 (10)0.0103 (9)0.0125 (8)0.0009 (9)
C60.0366 (9)0.0465 (11)0.0399 (10)0.0028 (8)0.0145 (8)0.0024 (8)
C70.0381 (10)0.0425 (11)0.0492 (12)0.0048 (8)0.0187 (9)0.0006 (9)
C80.0402 (10)0.0335 (9)0.0424 (11)0.0010 (8)0.0215 (8)0.0003 (8)
C90.0362 (9)0.0351 (9)0.0323 (9)0.0024 (7)0.0160 (8)0.0009 (7)
C100.0331 (9)0.0401 (10)0.0320 (9)0.0000 (7)0.0143 (8)0.0012 (7)
C110.0340 (9)0.0450 (10)0.0324 (9)0.0049 (8)0.0136 (8)0.0034 (8)
C120.0358 (9)0.0415 (10)0.0352 (10)0.0054 (8)0.0174 (8)0.0026 (8)
C130.0352 (9)0.0366 (9)0.0341 (9)0.0000 (7)0.0167 (8)0.0017 (7)
C140.0524 (12)0.0540 (13)0.0575 (14)0.0137 (10)0.0210 (11)0.0055 (10)
C150.0432 (11)0.0692 (15)0.0485 (13)0.0118 (11)0.0084 (10)0.0017 (11)
C160.0478 (12)0.0498 (12)0.0728 (16)0.0003 (10)0.0252 (11)0.0086 (11)
C170.0466 (11)0.0529 (12)0.0578 (14)0.0114 (10)0.0236 (10)0.0036 (10)
C180.0356 (9)0.0382 (10)0.0303 (9)0.0028 (7)0.0139 (7)0.0010 (7)
C190.0401 (10)0.0422 (10)0.0318 (9)0.0035 (8)0.0120 (8)0.0005 (8)
C200.0506 (11)0.0550 (12)0.0338 (10)0.0132 (10)0.0198 (9)0.0049 (9)
C210.0542 (12)0.0544 (13)0.0502 (13)0.0108 (10)0.0322 (11)0.0170 (10)
C220.0553 (12)0.0459 (12)0.0600 (14)0.0058 (10)0.0270 (11)0.0067 (10)
C230.0521 (11)0.0431 (11)0.0396 (11)0.0056 (9)0.0202 (9)0.0033 (8)
Geometric parameters (Å, º) top
Cl1—C191.734 (2)C9—C101.508 (2)
Cl2—C211.741 (2)C9—C131.509 (2)
O1—C111.371 (2)C9—C181.525 (2)
O1—C121.372 (2)C9—H90.9800
O2—C11.220 (2)C10—C111.337 (2)
O3—C81.223 (2)C12—C131.334 (2)
C1—C101.465 (3)C14—H14A0.9600
C1—C21.504 (3)C14—H14B0.9600
C2—C31.522 (3)C14—H14C0.9600
C2—H2A0.9700C15—H15A0.9600
C2—H2B0.9700C15—H15B0.9600
C3—C171.526 (3)C15—H15C0.9600
C3—C161.528 (3)C16—H16A0.9600
C3—C41.531 (3)C16—H16B0.9600
C4—C111.482 (3)C16—H16C0.9600
C4—H4A0.9700C17—H17A0.9600
C4—H4B0.9700C17—H17B0.9600
C5—C121.486 (3)C17—H17C0.9600
C5—C61.525 (3)C18—C231.386 (3)
C5—H5A0.9700C18—C191.388 (2)
C5—H5B0.9700C19—C201.384 (3)
C6—C151.524 (3)C20—C211.371 (3)
C6—C141.524 (3)C20—H200.9300
C6—C71.531 (3)C21—C221.360 (3)
C7—C81.505 (3)C22—C231.383 (3)
C7—H7A0.9700C22—H220.9300
C7—H7B0.9700C23—H230.9300
C8—C131.468 (2)
C11—O1—C12118.07 (14)C10—C11—O1122.95 (16)
O2—C1—C10120.39 (18)C10—C11—C4126.02 (16)
O2—C1—C2121.29 (17)O1—C11—C4111.03 (15)
C10—C1—C2118.28 (17)C13—C12—O1123.39 (16)
C1—C2—C3115.27 (15)C13—C12—C5125.20 (17)
C1—C2—H2A108.5O1—C12—C5111.40 (15)
C3—C2—H2A108.5C12—C13—C8118.18 (16)
C1—C2—H2B108.5C12—C13—C9122.91 (16)
C3—C2—H2B108.5C8—C13—C9118.91 (15)
H2A—C2—H2B107.5C6—C14—H14A109.5
C2—C3—C17109.89 (16)C6—C14—H14B109.5
C2—C3—C16110.57 (17)H14A—C14—H14B109.5
C17—C3—C16109.31 (17)C6—C14—H14C109.5
C2—C3—C4107.56 (16)H14A—C14—H14C109.5
C17—C3—C4109.51 (16)H14B—C14—H14C109.5
C16—C3—C4109.97 (16)C6—C15—H15A109.5
C11—C4—C3112.57 (16)C6—C15—H15B109.5
C11—C4—H4A109.1H15A—C15—H15B109.5
C3—C4—H4A109.1C6—C15—H15C109.5
C11—C4—H4B109.1H15A—C15—H15C109.5
C3—C4—H4B109.1H15B—C15—H15C109.5
H4A—C4—H4B107.8C3—C16—H16A109.5
C12—C5—C6111.83 (15)C3—C16—H16B109.5
C12—C5—H5A109.2H16A—C16—H16B109.5
C6—C5—H5A109.2C3—C16—H16C109.5
C12—C5—H5B109.2H16A—C16—H16C109.5
C6—C5—H5B109.2H16B—C16—H16C109.5
H5A—C5—H5B107.9C3—C17—H17A109.5
C15—C6—C14109.56 (17)C3—C17—H17B109.5
C15—C6—C5109.34 (16)H17A—C17—H17B109.5
C14—C6—C5110.85 (17)C3—C17—H17C109.5
C15—C6—C7110.20 (17)H17A—C17—H17C109.5
C14—C6—C7109.58 (17)H17B—C17—H17C109.5
C5—C6—C7107.28 (16)C23—C18—C19116.87 (17)
C8—C7—C6114.26 (16)C23—C18—C9118.85 (16)
C8—C7—H7A108.7C19—C18—C9124.25 (16)
C6—C7—H7A108.7C20—C19—C18121.75 (18)
C8—C7—H7B108.7C20—C19—Cl1117.22 (15)
C6—C7—H7B108.7C18—C19—Cl1121.03 (15)
H7A—C7—H7B107.6C21—C20—C19118.76 (19)
O3—C8—C13120.01 (17)C21—C20—H20120.6
O3—C8—C7121.26 (17)C19—C20—H20120.6
C13—C8—C7118.70 (16)C22—C21—C20121.69 (19)
C10—C9—C13109.02 (14)C22—C21—Cl2119.39 (18)
C10—C9—C18111.39 (14)C20—C21—Cl2118.91 (17)
C13—C9—C18110.31 (14)C21—C22—C23118.6 (2)
C10—C9—H9108.7C21—C22—H22120.7
C13—C9—H9108.7C23—C22—H22120.7
C18—C9—H9108.7C22—C23—C18122.25 (19)
C11—C10—C1118.05 (17)C22—C23—H23118.9
C11—C10—C9123.28 (16)C18—C23—H23118.9
C1—C10—C9118.66 (16)

Experimental details

Crystal data
Chemical formulaC23H24Cl2O3
Mr419.32
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)9.8154 (10), 19.833 (2), 11.4441 (11)
β (°) 111.873 (2)
V3)2067.4 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.34
Crystal size (mm)0.20 × 0.10 × 0.10
Data collection
DiffractometerBruker APEX CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 1997)
Tmin, Tmax0.936, 0.967
No. of measured, independent and
observed [I > 2σ(I)] reflections
13137, 4961, 3331
Rint0.027
(sin θ/λ)max1)0.665
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.124, 1.02
No. of reflections4961
No. of parameters257
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.36, 0.55

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

The research was supported by the Natural Science Foundation of Zhejiang Province (grant No. Y2090552). The author thanks Dr Dan Zhao of the Henan Polytechnic University for the data collection and structure refinement.

References

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