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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 2| February 2013| Pages o314-o315

1-(4-{2-[(E)-3-(4-Chloro­phen­yl)-3-oxo­prop-1-en-1-yl]phen­­oxy}but­yl)-1H-indole-3-carbaldehyde

aPost Graduate and Research Department of Physics, Agurchand Manmull Jain College, Chennai 600 114, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
*Correspondence e-mail: seshadri_pr@yahoo.com

(Received 15 January 2013; accepted 24 January 2013; online 31 January 2013)

In the title compound, C28H24ClNO3, the dihedral angles between the central benzene ring and the indole ring system and the chlorobenzene ring are 70.81 (5) and 78.62 (5)°, respectively. The mol­ecular structure is stabilized by a weak intra­molecular C—H⋯O inter­action. In the crystal, pairs of C—H⋯O hydrogen bonds link the mol­ecules into inversion dimers with an R22(14) motif.

Related literature

For the biological activity of indole derivatives, see: Olgen & Coban (2003[Olgen, S. & Coban, T. (2003). Biol. Pharm. Bull. 26, 736-738.]); Ho et al. (1986[Ho, C. Y., Haegman, W. E. & Perisco, F. (1986). J. Med. Chem. 29, 118-121.]); Joshi & Chand (1982[Joshi, K. C. & Chand, P. (1982). Pharmazie, 37, 1-12.]); Rodriguez et al. (1985[Rodriguez, J. G., Temprano, F., Esteban-Calderon, C., Martinez-Ripoll, M. & Garcia-Blanco, S. (1985). Tetrahedron, 41, 3813-3823.]); Okabe & Adachi (1998[Okabe, N. & Adachi, Y. (1998). Acta Cryst. C54, 386-387.]); Merck (1973[Merck (1973). French Patent No. 2163554.]). For N-atom hybridization, see: Beddoes et al. (1986[Beddoes, R. L., Dalton, L., Joule, T. A., Mills, O. S., Street, J. D. & Watt, C. I. F. (1986). J. Chem. Soc. Perkin Trans. 2, pp. 787-797.]). For a related structure, see: Paramasivam et al. (2012[Paramasivam, S., Bhaskar, G., Seshadri, P. R. & Perumal, P. T. (2012). Acta Cryst. E68, o683-o684.]). For graph-set notation see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C28H24ClNO3

  • Mr = 457.93

  • Monoclinic, P 21 /n

  • a = 8.7126 (3) Å

  • b = 19.1311 (6) Å

  • c = 13.9338 (4) Å

  • β = 93.198 (2)°

  • V = 2318.89 (13) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.20 mm−1

  • T = 298 K

  • 0.20 × 0.20 × 0.20 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • 22253 measured reflections

  • 5782 independent reflections

  • 4060 reflections with I > 2σ(I)

  • Rint = 0.026

Refinement
  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.145

  • S = 1.03

  • 5782 reflections

  • 298 parameters

  • H-atom parameters constrained

  • Δρmax = 0.39 e Å−3

  • Δρmin = −0.46 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C8—H8⋯O2 0.93 2.26 2.850 (2) 121
C20—H20⋯O1i 0.93 2.52 3.374 (2) 152
Symmetry code: (i) -x, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 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: ORTEP-3 for Windowa (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97, PLATON and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

Indole derivatives exhibit antioxidant (Olgen & Coban, 2003), central nervous system depressant and muscle relaxant properties (Ho et al., 1986), antifungicidal (Joshi & Chand, 1982), antimicrobial, antiinflammatory and antiimplantation (Rodriguez et al., 1985), antibacterial (Okabe & Adachi, 1998) and antihypertensive (Merck, 1973) activities. Against this background, the title compound was chosen for X-ray structure analysis (Fig. 1).

The indole ring is planar and it makes the dihedral angle with the chlorophenyl ring of 78.62 (05)°.

The sum of the bond angles around N1 [359.94 (44)°] indicates sp2 hybridization (Beddoes et al., 1986). The geometric parameters of the title molecule (Fig. 1) agree well with reported similar structure (Paramasivam et al., 2012).

The molecular structure is stabilised by a weak C—H···O intramolecular interaction and the crystal packing reveals a weak C—H···O hydrogen bonds (Fig. 2). In the crystal structure, the molecules at (x, y, z) and (- x, - y + 1, - z + 2) are linked by C20—H20···O1 hydrogen bond, generating a centrosymmetric dimeric ring motif R22(14) (Bernstein et al., 1995).

Related literature top

For the biological activity of indole derivatives, see: Olgen & Coban (2003); Ho et al. (1986); Joshi & Chand (1982); Rodriguez et al. (1985); Okabe & Adachi (1998); Merck (1973). For N-atom hybridization, see: Beddoes et al. (1986). For a related structure, see: Paramasivam et al. (2012). For graph set notation see: Bernstein et al. (1995).

Experimental top

2 g (13.7 mmol) of 1H-indole-3-carbaldehyde in 25 mL dry DMF and anhydrous potassium carbonate (2 g, 13.7 mmol) were stirred for 15 min at room temperature followed by addition of 5.4 g (13.7 mmol) of (E)-3-(2-(4-bromobutoxy)phenyl)-1-(4-chlorophenyl)prop-2-en-1-one in 30 mL dry DMF with continued stirring for about 3 h at room temperature. After the completion of the reaction as evidenced from TLC, the solvent was filtered into crushed ice and extracted with chloroform. The organic extract was dried over Na2SO4 and concentrated under reduced pressure. Chromatography of the residue eluting with hexane/ethyl acetate mixture (8:2) gave pure (E)-1-(4-(2-(3-(4-chlorophenyl)-3-oxoprop-1-enyl)phenoxy)butyl)-1H-indole-3-carbaldehyde in good yield.

Refinement top

Hydrogen atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93 - 0.97 Å and Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2 Ueq(C) for other H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windowa (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. The crystal packing of the title compound. Hydrogen bonds are shown by dashed lines.
1-(4-{2-[(E)-3-(4-Chlorophenyl)-3-oxoprop-1-en-1-yl]phenoxy}butyl)-1H-indole-3-carbaldehyde top
Crystal data top
C28H24ClNO3F(000) = 960
Mr = 457.93monoclinic
Monoclinic, P21/nDx = 1.312 Mg m3
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 8.7126 (3) ÅCell parameters from 5782 reflections
b = 19.1311 (6) Åθ = 1.8–28.3°
c = 13.9338 (4) ŵ = 0.20 mm1
β = 93.198 (2)°T = 298 K
V = 2318.89 (13) Å3Block, colourless
Z = 40.20 × 0.20 × 0.20 mm
Data collection top
Bruker SMART APEXII area-detector
diffractometer
4060 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
Graphite monochromatorθmax = 28.3°, θmin = 1.8°
ω and ϕ scansh = 811
22253 measured reflectionsk = 2521
5782 independent reflectionsl = 1818
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0591P)2 + 0.7822P]
where P = (Fo2 + 2Fc2)/3
5782 reflections(Δ/σ)max < 0.001
298 parametersΔρmax = 0.39 e Å3
0 restraintsΔρmin = 0.46 e Å3
Crystal data top
C28H24ClNO3V = 2318.89 (13) Å3
Mr = 457.93Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.7126 (3) ŵ = 0.20 mm1
b = 19.1311 (6) ÅT = 298 K
c = 13.9338 (4) Å0.20 × 0.20 × 0.20 mm
β = 93.198 (2)°
Data collection top
Bruker SMART APEXII area-detector
diffractometer
4060 reflections with I > 2σ(I)
22253 measured reflectionsRint = 0.026
5782 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.145H-atom parameters constrained
S = 1.03Δρmax = 0.39 e Å3
5782 reflectionsΔρmin = 0.46 e Å3
298 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
C10.0037 (3)0.70610 (12)0.90463 (15)0.0675 (5)
C20.0110 (3)0.63646 (12)0.88447 (16)0.0743 (6)
H20.03510.61770.82840.089*
C30.0951 (3)0.59454 (11)0.94836 (14)0.0656 (5)
H30.10710.54740.93410.079*
C40.1623 (2)0.62099 (10)1.03343 (13)0.0526 (4)
C50.1383 (3)0.69100 (11)1.05371 (16)0.0700 (6)
H50.17810.70951.11160.084*
C60.0566 (3)0.73364 (12)0.98970 (18)0.0776 (7)
H60.04230.78061.00390.093*
C70.2526 (2)0.57743 (10)1.10492 (13)0.0559 (4)
C80.3047 (2)0.50761 (10)1.07578 (13)0.0552 (4)
H80.28420.49261.01290.066*
C90.3803 (2)0.46590 (9)1.13797 (12)0.0488 (4)
H90.39430.48421.19970.059*
C100.44511 (19)0.39676 (9)1.12663 (11)0.0450 (4)
C110.5351 (2)0.36906 (10)1.20364 (12)0.0535 (4)
H110.55110.39581.25900.064*
C120.6008 (3)0.30409 (11)1.20085 (14)0.0647 (5)
H120.66050.28741.25330.078*
C130.5775 (3)0.26396 (11)1.11985 (15)0.0688 (6)
H130.62210.21991.11740.083*
C140.4884 (3)0.28835 (10)1.04196 (13)0.0609 (5)
H140.47230.26040.98780.073*
C150.4230 (2)0.35419 (9)1.04394 (11)0.0472 (4)
C160.2994 (3)0.33837 (10)0.88721 (13)0.0632 (5)
H16A0.24910.29580.90630.076*
H16B0.39210.32600.85580.076*
C170.1931 (3)0.38074 (11)0.82024 (13)0.0612 (5)
H17A0.15200.35060.76900.073*
H17B0.10740.39730.85560.073*
C180.2704 (2)0.44254 (11)0.77648 (12)0.0571 (5)
H18A0.35090.42580.73700.068*
H18B0.31830.47080.82760.068*
C190.1603 (2)0.48804 (10)0.71534 (12)0.0583 (5)
H19A0.08240.50640.75560.070*
H19B0.21670.52740.69110.070*
C200.0653 (2)0.43252 (9)0.62598 (12)0.0485 (4)
H200.13540.44000.67290.058*
C210.09949 (19)0.40123 (9)0.53853 (11)0.0445 (4)
C220.2501 (2)0.37870 (11)0.50518 (14)0.0564 (5)
H220.32840.38320.54750.068*
C230.04045 (18)0.39990 (8)0.48909 (11)0.0404 (3)
C240.15337 (18)0.43141 (8)0.55073 (11)0.0420 (3)
C250.3043 (2)0.43976 (10)0.52522 (13)0.0526 (4)
H250.37790.46090.56650.063*
C260.3401 (2)0.41551 (11)0.43653 (14)0.0596 (5)
H260.44000.42070.41720.071*
C270.2308 (2)0.38327 (11)0.37477 (13)0.0583 (5)
H270.25940.36680.31550.070*
C280.0807 (2)0.37520 (10)0.39963 (11)0.0492 (4)
H280.00820.35380.35780.059*
N10.08465 (17)0.45088 (7)0.63409 (9)0.0469 (3)
O10.2827 (2)0.59973 (9)1.18603 (10)0.0837 (5)
O20.33578 (16)0.38163 (6)0.96938 (8)0.0570 (3)
O30.28421 (16)0.35426 (9)0.42671 (11)0.0757 (4)
Cl10.10168 (10)0.76018 (4)0.82139 (5)0.1058 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0800 (14)0.0584 (12)0.0639 (12)0.0172 (11)0.0030 (10)0.0019 (10)
C20.0966 (17)0.0648 (14)0.0599 (12)0.0149 (12)0.0089 (11)0.0127 (10)
C30.0897 (15)0.0488 (11)0.0576 (11)0.0095 (10)0.0022 (10)0.0117 (9)
C40.0585 (10)0.0466 (10)0.0532 (9)0.0020 (8)0.0097 (8)0.0081 (8)
C50.0835 (15)0.0548 (12)0.0704 (13)0.0083 (11)0.0079 (11)0.0187 (10)
C60.0954 (17)0.0479 (12)0.0880 (16)0.0151 (11)0.0086 (13)0.0162 (11)
C70.0657 (11)0.0528 (11)0.0494 (9)0.0014 (9)0.0058 (8)0.0109 (8)
C80.0714 (12)0.0496 (11)0.0441 (9)0.0032 (9)0.0005 (8)0.0074 (8)
C90.0542 (10)0.0505 (10)0.0416 (8)0.0067 (8)0.0022 (7)0.0085 (7)
C100.0502 (9)0.0462 (9)0.0384 (7)0.0065 (7)0.0006 (6)0.0016 (7)
C110.0612 (11)0.0578 (11)0.0405 (8)0.0055 (9)0.0066 (7)0.0034 (8)
C120.0793 (14)0.0593 (12)0.0532 (10)0.0047 (10)0.0170 (9)0.0061 (9)
C130.0935 (15)0.0495 (12)0.0615 (11)0.0115 (11)0.0135 (11)0.0028 (9)
C140.0893 (14)0.0453 (10)0.0466 (9)0.0052 (10)0.0090 (9)0.0045 (8)
C150.0603 (10)0.0439 (9)0.0369 (7)0.0039 (8)0.0040 (7)0.0006 (7)
C160.0968 (15)0.0458 (10)0.0446 (9)0.0043 (10)0.0178 (9)0.0066 (8)
C170.0779 (13)0.0559 (12)0.0475 (9)0.0123 (10)0.0173 (9)0.0022 (8)
C180.0674 (11)0.0611 (12)0.0414 (8)0.0094 (9)0.0101 (8)0.0029 (8)
C190.0799 (13)0.0482 (11)0.0452 (9)0.0041 (9)0.0111 (9)0.0047 (8)
C200.0539 (10)0.0498 (10)0.0417 (8)0.0056 (8)0.0022 (7)0.0074 (7)
C210.0471 (9)0.0440 (9)0.0415 (8)0.0005 (7)0.0035 (6)0.0086 (7)
C220.0489 (10)0.0632 (12)0.0565 (10)0.0022 (8)0.0014 (8)0.0116 (9)
C230.0458 (8)0.0368 (8)0.0377 (7)0.0003 (6)0.0057 (6)0.0084 (6)
C240.0482 (9)0.0373 (8)0.0397 (7)0.0006 (7)0.0046 (6)0.0060 (6)
C250.0482 (9)0.0525 (11)0.0560 (10)0.0046 (8)0.0082 (7)0.0065 (8)
C260.0476 (10)0.0700 (13)0.0613 (11)0.0019 (9)0.0047 (8)0.0082 (10)
C270.0614 (11)0.0666 (13)0.0473 (9)0.0066 (9)0.0075 (8)0.0010 (8)
C280.0569 (10)0.0498 (10)0.0401 (8)0.0007 (8)0.0051 (7)0.0022 (7)
N10.0575 (8)0.0443 (8)0.0380 (7)0.0004 (6)0.0065 (6)0.0009 (6)
O10.1221 (14)0.0712 (10)0.0562 (8)0.0217 (9)0.0091 (8)0.0221 (7)
O20.0842 (9)0.0449 (7)0.0396 (6)0.0066 (6)0.0160 (6)0.0055 (5)
O30.0594 (8)0.1004 (12)0.0651 (9)0.0151 (8)0.0157 (7)0.0039 (8)
Cl10.1481 (7)0.0834 (5)0.0832 (4)0.0471 (5)0.0170 (4)0.0014 (3)
Geometric parameters (Å, º) top
C1—C21.369 (3)C16—C171.513 (3)
C1—C61.374 (3)C16—H16A0.9700
C1—Cl11.742 (2)C16—H16B0.9700
C2—C31.378 (3)C17—C181.506 (3)
C2—H20.9300C17—H17A0.9700
C3—C41.388 (3)C17—H17B0.9700
C3—H30.9300C18—C191.520 (3)
C4—C51.387 (3)C18—H18A0.9700
C4—C71.489 (3)C18—H18B0.9700
C5—C61.377 (3)C19—N11.462 (2)
C5—H50.9300C19—H19A0.9700
C6—H60.9300C19—H19B0.9700
C7—O11.223 (2)C20—N11.352 (2)
C7—C81.475 (3)C20—C211.375 (2)
C8—C91.326 (3)C20—H200.9300
C8—H80.9300C21—C231.434 (2)
C9—C101.450 (3)C21—C221.434 (2)
C9—H90.9300C22—O31.211 (2)
C10—C111.398 (2)C22—H220.9300
C10—C151.415 (2)C23—C281.396 (2)
C11—C121.370 (3)C23—C241.405 (2)
C11—H110.9300C24—N11.387 (2)
C12—C131.371 (3)C24—C251.390 (2)
C12—H120.9300C25—C261.372 (3)
C13—C141.380 (3)C25—H250.9300
C13—H130.9300C26—C271.392 (3)
C14—C151.383 (3)C26—H260.9300
C14—H140.9300C27—C281.380 (3)
C15—O21.3583 (19)C27—H270.9300
C16—O21.434 (2)C28—H280.9300
C2—C1—C6121.0 (2)H16A—C16—H16B108.6
C2—C1—Cl1119.29 (18)C18—C17—C16113.45 (17)
C6—C1—Cl1119.75 (17)C18—C17—H17A108.9
C1—C2—C3119.1 (2)C16—C17—H17A108.9
C1—C2—H2120.5C18—C17—H17B108.9
C3—C2—H2120.5C16—C17—H17B108.9
C2—C3—C4121.55 (19)H17A—C17—H17B107.7
C2—C3—H3119.2C17—C18—C19113.20 (16)
C4—C3—H3119.2C17—C18—H18A108.9
C5—C4—C3117.70 (19)C19—C18—H18A108.9
C5—C4—C7118.95 (17)C17—C18—H18B108.9
C3—C4—C7123.30 (17)C19—C18—H18B108.9
C6—C5—C4121.2 (2)H18A—C18—H18B107.8
C6—C5—H5119.4N1—C19—C18113.48 (15)
C4—C5—H5119.4N1—C19—H19A108.9
C1—C6—C5119.4 (2)C18—C19—H19A108.9
C1—C6—H6120.3N1—C19—H19B108.9
C5—C6—H6120.3C18—C19—H19B108.9
O1—C7—C8121.14 (18)H19A—C19—H19B107.7
O1—C7—C4120.06 (17)N1—C20—C21110.35 (15)
C8—C7—C4118.80 (15)N1—C20—H20124.8
C9—C8—C7120.95 (16)C21—C20—H20124.8
C9—C8—H8119.5C20—C21—C23106.59 (14)
C7—C8—H8119.5C20—C21—C22124.54 (17)
C8—C9—C10131.29 (16)C23—C21—C22128.79 (16)
C8—C9—H9114.4O3—C22—C21125.64 (18)
C10—C9—H9114.4O3—C22—H22117.2
C11—C10—C15116.86 (16)C21—C22—H22117.2
C11—C10—C9117.85 (15)C28—C23—C24119.25 (15)
C15—C10—C9125.28 (15)C28—C23—C21134.26 (15)
C12—C11—C10122.66 (17)C24—C23—C21106.49 (14)
C12—C11—H11118.7N1—C24—C25129.92 (15)
C10—C11—H11118.7N1—C24—C23107.87 (14)
C11—C12—C13119.26 (18)C25—C24—C23122.20 (15)
C11—C12—H12120.4C26—C25—C24117.22 (17)
C13—C12—H12120.4C26—C25—H25121.4
C12—C13—C14120.61 (19)C24—C25—H25121.4
C12—C13—H13119.7C25—C26—C27121.62 (18)
C14—C13—H13119.7C25—C26—H26119.2
C13—C14—C15120.43 (17)C27—C26—H26119.2
C13—C14—H14119.8C28—C27—C26121.32 (17)
C15—C14—H14119.8C28—C27—H27119.3
O2—C15—C14123.39 (15)C26—C27—H27119.3
O2—C15—C10116.42 (15)C27—C28—C23118.38 (16)
C14—C15—C10120.19 (16)C27—C28—H28120.8
O2—C16—C17106.49 (16)C23—C28—H28120.8
O2—C16—H16A110.4C20—N1—C24108.69 (14)
C17—C16—H16A110.4C20—N1—C19125.67 (15)
O2—C16—H16B110.4C24—N1—C19125.58 (15)
C17—C16—H16B110.4C15—O2—C16118.49 (14)
C6—C1—C2—C33.7 (4)C17—C18—C19—N160.3 (2)
Cl1—C1—C2—C3176.83 (19)N1—C20—C21—C230.29 (19)
C1—C2—C3—C41.4 (4)N1—C20—C21—C22176.78 (16)
C2—C3—C4—C51.9 (3)C20—C21—C22—O3176.1 (2)
C2—C3—C4—C7179.3 (2)C23—C21—C22—O30.3 (3)
C3—C4—C5—C62.9 (3)C20—C21—C23—C28179.59 (18)
C7—C4—C5—C6179.5 (2)C22—C21—C23—C283.5 (3)
C2—C1—C6—C52.7 (4)C20—C21—C23—C240.24 (18)
Cl1—C1—C6—C5177.9 (2)C22—C21—C23—C24176.67 (17)
C4—C5—C6—C10.7 (4)C28—C23—C24—N1179.75 (14)
C5—C4—C7—O112.0 (3)C21—C23—C24—N10.11 (17)
C3—C4—C7—O1165.4 (2)C28—C23—C24—C250.9 (2)
C5—C4—C7—C8167.82 (19)C21—C23—C24—C25179.28 (15)
C3—C4—C7—C814.8 (3)N1—C24—C25—C26179.55 (17)
O1—C7—C8—C92.8 (3)C23—C24—C25—C260.3 (3)
C4—C7—C8—C9177.42 (18)C24—C25—C26—C270.6 (3)
C7—C8—C9—C10178.63 (18)C25—C26—C27—C280.9 (3)
C8—C9—C10—C11172.6 (2)C26—C27—C28—C230.3 (3)
C8—C9—C10—C158.3 (3)C24—C23—C28—C270.5 (2)
C15—C10—C11—C120.3 (3)C21—C23—C28—C27179.67 (18)
C9—C10—C11—C12179.50 (18)C21—C20—N1—C240.22 (19)
C10—C11—C12—C130.3 (3)C21—C20—N1—C19177.14 (15)
C11—C12—C13—C140.3 (4)C25—C24—N1—C20179.39 (17)
C12—C13—C14—C150.9 (4)C23—C24—N1—C200.06 (18)
C13—C14—C15—O2179.22 (19)C25—C24—N1—C192.0 (3)
C13—C14—C15—C100.9 (3)C23—C24—N1—C19177.31 (15)
C11—C10—C15—O2179.82 (15)C18—C19—N1—C20109.0 (2)
C9—C10—C15—O21.1 (3)C18—C19—N1—C2474.1 (2)
C11—C10—C15—C140.3 (3)C14—C15—O2—C165.0 (3)
C9—C10—C15—C14178.79 (18)C10—C15—O2—C16174.84 (17)
O2—C16—C17—C1868.2 (2)C17—C16—O2—C15176.03 (16)
C16—C17—C18—C19175.60 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···O20.932.262.850 (2)121
C9—H9···O10.932.422.791 (2)104
C20—H20···O1i0.932.523.374 (2)152
Symmetry code: (i) x, y+1, z+2.

Experimental details

Crystal data
Chemical formulaC28H24ClNO3
Mr457.93
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)8.7126 (3), 19.1311 (6), 13.9338 (4)
β (°) 93.198 (2)
V3)2318.89 (13)
Z4
Radiation typeMo Kα
µ (mm1)0.20
Crystal size (mm)0.20 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART APEXII area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
22253, 5782, 4060
Rint0.026
(sin θ/λ)max1)0.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.145, 1.03
No. of reflections5782
No. of parameters298
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.39, 0.46

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windowa (Farrugia, 2012) and PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···O20.932.262.850 (2)120.8
C20—H20···O1i0.932.523.374 (2)152.0
Symmetry code: (i) x, y+1, z+2.
 

Acknowledgements

The authors acknowledge the Technology Business Incubator (TBI), CAS in Crystallography, University of Madras, Chennai 600 025, India, for the data collection.

References

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Volume 69| Part 2| February 2013| Pages o314-o315
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