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Acta Crystallogr Sect E Struct Rep Online. 2009 March 1; 65(Pt 3): o514.
Published online 2009 February 11. doi:  10.1107/S1600536809003894
PMCID: PMC2968596

1,5-Bis(4-chloro­phen­yl)-3-[4-(dimethyl­amino)phen­yl]pentane-1,5-dione

Abstract

In the title mol­ecule, C25H23Cl2NO2, the central benzene ring forms dihedral angles of 81.88 (7) and 89.22 (7)° with the two 4-chloro­phenyl fragments. The crystal packing exhibits weak inter­molecular C—H(...)O hydrogen bonds and π–π inter­actions [centroid–centroid distance 3.724 (3) Å].

Related literature

For the crystal structures of related compounds, see: Das et al. (1994 [triangle]); Huang et al. (2006 [triangle]).

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Object name is e-65-0o514-scheme1.jpg

Experimental

Crystal data

  • C25H23Cl2NO2
  • M r = 440.34
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o514-efi1.jpg
  • a = 6.1059 (11) Å
  • b = 12.5660 (16) Å
  • c = 14.731 (2) Å
  • α = 75.516 (1)°
  • β = 85.953 (2)°
  • γ = 87.215 (2)°
  • V = 1091.1 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.32 mm−1
  • T = 298 (2) K
  • 0.49 × 0.44 × 0.41 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.859, T max = 0.880
  • 5699 measured reflections
  • 3783 independent reflections
  • 1846 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.051
  • wR(F 2) = 0.141
  • S = 0.99
  • 3783 reflections
  • 273 parameters
  • H-atom parameters constrained
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.28 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809003894/cv2508sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003894/cv2508Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This project was supported by the Foundation of Tianshui Normal University.

supplementary crystallographic information

Comment

In this paper, we present the crystal structure of the title compound, (I), obtained with the solvent-free protocol for the synthesis of 1,5-diketones starting from the fragrant aldehydes and fragrant ketones in the presence of NaOH under solvent-free conditions.

In (I) (Fig. 1), the bond lengths and angles are normal and correspond to those observed in 1,3,5-triphenyl-pentane-1,5-diketone (Das et al., 1994), 1,5-Diphenyl-3-(2-pyridyl)pentane-1,5-dione (Huang et al., 2006). The dihedral angles between the central benzene ring and the benzene rings C12/C13/C14/C15/C16/C17 and C6/C7/C8/C9/C10/C11 are 89.22 (7) ° and 81.88 (7) °, respectively. The crystal packing exhibits weak intermolecular π–π interactions (Table 1) and C—H···O hydrogen bonds (Table 2).

Experimental

4-(Dimethylamino)benzaldehyde (0.5 mmol) and 4-chloroacetophenone (1.0 mmol), NaOH (1.0 mmol) were mixed in 50 ml flask under sovlent-free condtions. After stirring for 5 min at 293 K, the resulting mixture was washed with water for several times for removing NaOH, and recrystalized from ethanol, and afforded the title compound as a crystalline solid. Elemental analysis: calculated for C25H23Cl2NO2: C 68.19, H 5.26, N 3.18%; found: C 68.23, H 5.35, N 3.15%.

Refinement

All H atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.98 Å and Uiso(H) = 1.2-1.5Ueq(C).

Figures

Fig. 1.
The molecular structure of (I) showing the atomic numbering scheme and 30% probability displacement ellipsoids. H atoms have been omitted for clarity.

Crystal data

C25H23Cl2NO2Z = 2
Mr = 440.34F(000) = 460
Triclinic, P1Dx = 1.340 Mg m3
a = 6.1059 (11) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.5660 (16) ÅCell parameters from 1234 reflections
c = 14.731 (2) Åθ = 2.5–22.3°
α = 75.516 (1)°µ = 0.32 mm1
β = 85.953 (2)°T = 298 K
γ = 87.215 (2)°Block, colourless
V = 1091.1 (3) Å30.49 × 0.44 × 0.41 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer3783 independent reflections
Radiation source: fine-focus sealed tube1846 reflections with I > 2σ(I)
graphiteRint = 0.024
[var phi] and ω scansθmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −7→7
Tmin = 0.859, Tmax = 0.880k = −8→14
5699 measured reflectionsl = −17→17

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H-atom parameters constrained
S = 0.99w = 1/[σ2(Fo2) + (0.0595P)2] where P = (Fo2 + 2Fc2)/3
3783 reflections(Δ/σ)max = 0.001
273 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = −0.28 e Å3

Special details

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)

xyzUiso*/Ueq
Cl11.1281 (2)0.35929 (8)0.70584 (7)0.1057 (4)
Cl20.8066 (2)1.57712 (9)0.06677 (8)0.1334 (5)
N10.5447 (5)0.8356 (3)0.0253 (2)0.0836 (9)
O10.4561 (4)0.75133 (19)0.48581 (16)0.0838 (8)
O20.3440 (4)1.12960 (19)0.32504 (17)0.0811 (7)
C10.6537 (6)0.7566 (3)0.4892 (2)0.0550 (8)
C20.7662 (5)0.8611 (2)0.4432 (2)0.0560 (8)
H2A0.89800.84410.40800.067*
H2B0.81090.89430.49140.067*
C30.6236 (5)0.9442 (2)0.3771 (2)0.0551 (8)
H30.47550.94190.40760.066*
C40.7007 (5)1.0611 (2)0.3626 (2)0.0587 (9)
H4A0.72391.07440.42320.070*
H4B0.84031.06850.32620.070*
C50.5388 (6)1.1462 (3)0.3128 (2)0.0556 (8)
C60.7791 (5)0.6593 (2)0.54189 (19)0.0486 (8)
C70.9857 (5)0.6658 (3)0.5707 (2)0.0573 (8)
H71.05490.73280.55480.069*
C81.0912 (6)0.5741 (3)0.6229 (2)0.0667 (9)
H81.22970.57930.64370.080*
C90.9908 (7)0.4750 (3)0.6441 (2)0.0650 (9)
C100.7867 (7)0.4664 (3)0.6155 (2)0.0744 (10)
H100.72020.39870.62940.089*
C110.6806 (6)0.5591 (3)0.5657 (2)0.0635 (9)
H110.53920.55410.54760.076*
C120.6156 (6)1.2513 (3)0.2519 (2)0.0546 (8)
C130.8291 (6)1.2674 (3)0.2151 (2)0.0632 (9)
H130.93471.21090.22980.076*
C140.8859 (6)1.3673 (3)0.1565 (2)0.0779 (11)
H141.02881.37790.13040.093*
C150.7308 (8)1.4511 (3)0.1368 (2)0.0804 (11)
C160.5199 (8)1.4378 (3)0.1735 (2)0.0854 (12)
H160.41641.49550.16040.102*
C170.4640 (6)1.3385 (3)0.2298 (2)0.0707 (10)
H170.31981.32860.25440.085*
C180.6048 (5)0.9143 (2)0.2842 (2)0.0490 (8)
C190.7708 (5)0.9307 (2)0.2150 (2)0.0572 (8)
H190.90030.96030.22580.069*
C200.7540 (6)0.9053 (3)0.1304 (2)0.0632 (9)
H200.87050.91890.08530.076*
C210.5653 (6)0.8595 (3)0.1113 (2)0.0596 (9)
C220.3988 (6)0.8402 (3)0.1817 (2)0.0663 (9)
H220.27110.80790.17230.080*
C230.4195 (5)0.8681 (2)0.2655 (2)0.0597 (9)
H230.30350.85510.31090.072*
C240.7091 (7)0.8654 (3)−0.0499 (3)0.0939 (13)
H24A0.74290.9413−0.05880.141*
H24B0.65540.8546−0.10660.141*
H24C0.83930.8202−0.03480.141*
C250.3520 (7)0.7852 (4)0.0080 (3)0.1137 (16)
H25A0.31250.72670.06170.171*
H25B0.38060.7559−0.04610.171*
H25C0.23340.8390−0.00310.171*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.1403 (11)0.0722 (7)0.0954 (8)0.0259 (6)−0.0218 (7)−0.0052 (6)
Cl20.1990 (14)0.0788 (8)0.0976 (9)0.0017 (8)0.0142 (9)0.0169 (6)
N10.092 (3)0.096 (2)0.072 (2)0.0026 (19)−0.0208 (19)−0.0359 (19)
O10.0554 (16)0.0829 (18)0.0964 (19)−0.0125 (13)−0.0049 (14)0.0110 (14)
O20.0617 (17)0.0758 (18)0.103 (2)0.0036 (14)−0.0004 (14)−0.0203 (14)
C10.050 (2)0.068 (2)0.0468 (19)−0.0123 (18)0.0025 (16)−0.0132 (17)
C20.059 (2)0.060 (2)0.0468 (18)−0.0079 (17)−0.0023 (16)−0.0077 (16)
C30.054 (2)0.057 (2)0.052 (2)−0.0022 (16)−0.0017 (16)−0.0100 (16)
C40.069 (2)0.057 (2)0.0517 (19)0.0013 (18)−0.0075 (17)−0.0152 (16)
C50.059 (2)0.060 (2)0.053 (2)0.0031 (19)−0.0031 (18)−0.0243 (18)
C60.051 (2)0.053 (2)0.0420 (18)−0.0077 (17)0.0049 (15)−0.0128 (15)
C70.053 (2)0.057 (2)0.061 (2)−0.0062 (17)−0.0018 (17)−0.0117 (17)
C80.063 (2)0.069 (3)0.067 (2)−0.001 (2)−0.0065 (18)−0.015 (2)
C90.088 (3)0.054 (2)0.052 (2)0.007 (2)−0.0023 (19)−0.0143 (18)
C100.095 (3)0.054 (2)0.076 (3)−0.017 (2)−0.004 (2)−0.017 (2)
C110.066 (2)0.058 (2)0.069 (2)−0.0129 (19)−0.0041 (19)−0.0183 (19)
C120.067 (2)0.055 (2)0.0439 (19)0.0068 (18)−0.0083 (17)−0.0152 (16)
C130.070 (3)0.063 (2)0.053 (2)0.0080 (19)−0.0059 (18)−0.0078 (18)
C140.083 (3)0.083 (3)0.061 (2)−0.002 (2)−0.002 (2)−0.005 (2)
C150.112 (4)0.064 (3)0.054 (2)0.009 (2)−0.002 (2)0.0012 (19)
C160.110 (4)0.074 (3)0.061 (2)0.027 (2)−0.007 (2)−0.002 (2)
C170.079 (3)0.075 (3)0.054 (2)0.014 (2)−0.0021 (19)−0.012 (2)
C180.048 (2)0.0485 (19)0.0488 (19)0.0037 (15)−0.0034 (16)−0.0098 (15)
C190.052 (2)0.061 (2)0.061 (2)−0.0015 (16)−0.0095 (17)−0.0180 (17)
C200.060 (2)0.069 (2)0.059 (2)0.0039 (18)0.0010 (17)−0.0168 (18)
C210.071 (2)0.052 (2)0.056 (2)0.0113 (18)−0.0178 (19)−0.0124 (17)
C220.063 (2)0.065 (2)0.073 (3)−0.0064 (18)−0.018 (2)−0.0177 (19)
C230.052 (2)0.064 (2)0.060 (2)−0.0028 (17)−0.0035 (17)−0.0077 (18)
C240.114 (3)0.109 (3)0.063 (3)0.018 (3)−0.012 (2)−0.032 (2)
C250.107 (4)0.145 (4)0.115 (4)0.007 (3)−0.039 (3)−0.074 (3)

Geometric parameters (Å, °)

Cl1—C91.724 (3)C11—H110.9300
Cl2—C151.724 (4)C12—C131.380 (4)
N1—C211.389 (4)C12—C171.389 (4)
N1—C241.430 (4)C13—C141.378 (5)
N1—C251.431 (4)C13—H130.9300
O1—C11.217 (3)C14—C151.371 (5)
O2—C51.211 (3)C14—H140.9300
C1—C61.484 (4)C15—C161.362 (5)
C1—C21.495 (4)C16—C171.359 (5)
C2—C31.523 (4)C16—H160.9300
C2—H2A0.9700C17—H170.9300
C2—H2B0.9700C18—C191.371 (4)
C3—C181.519 (4)C18—C231.372 (4)
C3—C41.523 (4)C19—C201.373 (4)
C3—H30.9800C19—H190.9300
C4—C51.505 (4)C20—C211.389 (4)
C4—H4A0.9700C20—H200.9300
C4—H4B0.9700C21—C221.384 (4)
C5—C121.476 (4)C22—C231.381 (4)
C6—C71.371 (4)C22—H220.9300
C6—C111.376 (4)C23—H230.9300
C7—C81.374 (4)C24—H24A0.9600
C7—H70.9300C24—H24B0.9600
C8—C91.370 (4)C24—H24C0.9600
C8—H80.9300C25—H25A0.9600
C9—C101.361 (4)C25—H25B0.9600
C10—C111.371 (5)C25—H25C0.9600
C10—H100.9300
Cg···Cgi3.724 (3)
C21—N1—C24121.3 (3)C17—C12—C5118.1 (3)
C21—N1—C25120.5 (3)C14—C13—C12120.0 (3)
C24—N1—C25118.1 (3)C14—C13—H13120.0
O1—C1—C6119.2 (3)C12—C13—H13120.0
O1—C1—C2120.1 (3)C15—C14—C13119.7 (4)
C6—C1—C2120.8 (3)C15—C14—H14120.1
C1—C2—C3113.6 (3)C13—C14—H14120.1
C1—C2—H2A108.9C16—C15—C14121.4 (4)
C3—C2—H2A108.9C16—C15—Cl2119.4 (3)
C1—C2—H2B108.9C14—C15—Cl2119.2 (4)
C3—C2—H2B108.9C17—C16—C15118.6 (4)
H2A—C2—H2B107.7C17—C16—H16120.7
C18—C3—C4111.8 (2)C15—C16—H16120.7
C18—C3—C2112.2 (2)C16—C17—C12122.0 (4)
C4—C3—C2111.8 (2)C16—C17—H17119.0
C18—C3—H3106.9C12—C17—H17119.0
C4—C3—H3106.9C19—C18—C23116.2 (3)
C2—C3—H3106.9C19—C18—C3122.4 (3)
C5—C4—C3112.6 (3)C23—C18—C3121.4 (3)
C5—C4—H4A109.1C18—C19—C20122.8 (3)
C3—C4—H4A109.1C18—C19—H19118.6
C5—C4—H4B109.1C20—C19—H19118.6
C3—C4—H4B109.1C19—C20—C21120.9 (3)
H4A—C4—H4B107.8C19—C20—H20119.6
O2—C5—C12119.8 (3)C21—C20—H20119.6
O2—C5—C4119.8 (3)C22—C21—C20116.8 (3)
C12—C5—C4120.4 (3)C22—C21—N1121.9 (3)
C7—C6—C11118.7 (3)C20—C21—N1121.3 (3)
C7—C6—C1122.8 (3)C23—C22—C21121.0 (3)
C11—C6—C1118.5 (3)C23—C22—H22119.5
C6—C7—C8120.5 (3)C21—C22—H22119.5
C6—C7—H7119.7C18—C23—C22122.4 (3)
C8—C7—H7119.7C18—C23—H23118.8
C9—C8—C7119.5 (3)C22—C23—H23118.8
C9—C8—H8120.2N1—C24—H24A109.5
C7—C8—H8120.2N1—C24—H24B109.5
C10—C9—C8120.9 (3)H24A—C24—H24B109.5
C10—C9—Cl1119.7 (3)N1—C24—H24C109.5
C8—C9—Cl1119.3 (3)H24A—C24—H24C109.5
C9—C10—C11119.0 (3)H24B—C24—H24C109.5
C9—C10—H10120.5N1—C25—H25A109.5
C11—C10—H10120.5N1—C25—H25B109.5
C10—C11—C6121.3 (3)H25A—C25—H25B109.5
C10—C11—H11119.4N1—C25—H25C109.5
C6—C11—H11119.4H25A—C25—H25C109.5
C13—C12—C17118.3 (3)H25B—C25—H25C109.5
C13—C12—C5123.7 (3)

Symmetry codes: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C7—H7···O1ii0.932.583.176 (4)122

Symmetry codes: (ii) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2508).

References

  • Das, G. C., Hursthouse, M. B., Malik, K. M. A., Rahman, M. M., Rahman, M. T. & Olsson, T. (1994). J. Chem. Crystallogr.24, 511–515.
  • Huang, X.-Q., Wang, D.-Q., Dou, J.-M. & Wang, J.-X. (2006). Acta Cryst. E62, o60–o61.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

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