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

Journal logoSTRUCTURAL
CHEMISTRY
ISSN: 2053-2296
Volume 62| Part 1| January 2006| Pages o39-o41
doi:10.1107/S0108270105039193

1,5-Bis(4-chloro­phen­yl)-3-(2-chloro­quinolin-3-yl)pentane-1,5-dione: sheets of R44(26) rings built from C—H⋯N and C—H⋯O hydrogen bonds

CROSSMARK_Color_square_no_text.svg
Braulio Insuasty,a Harlen Torres,b Justo Cobo,c John N. Lowd and Christopher Glidewelle*

aGrupo de Investigación de Compuestos Heterocíclicos, Departamento de Química, Universidad de Valle, AA 25360 Cali, Colombia, bDepartamento de Ciencias Básicas, Universidad Nacional de Colombia Sede Palmira, Crra. 32, Chapinero vía Candelaria, AA 237 Palmira-Valle, Colombia, cDepartamento de Química Inorgán­ica y Orgánica, Universidad de Jaén, 23071 Jaén, Spain, dDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, and eSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland
*Correspondence e-mail: cg@st-andrews.ac.uk

(Received 24 November 2005; accepted 25 November 2005; online 24 December 2005)

Mol­ecules of the title compound, C26H18Cl3NO2, are linked into sheets of R44(26) rings by a combination of C—H⋯N and C—H⋯O hydrogen bonds.

Similar articles

Comment

With the aim of developing new classes of fused heterocyclic systems, we have prepared a range of novel chalcones appropriately functionalized for use as inter­mediates. The reactions used to prepare such chalcones involve methyl aryl ketones and aryl or heteroaryl aldehydes. We report here the structure of the title compound, (I)[link] (Fig. 1[link]), obtained in low yield as a by-product in the preparation of the pyrazolyl­quinoline (II)[link] via the corresponding chalcone (III)[link], formed by the reaction between 2-chloroquinoline-3-carbaldehyde and 4-chloro­phenyl methyl ketone.

The bond distances within the quinoline portion of the mol­ecule (Table 1[link]) show evidence for significant bond fixation; the N31—C32 bond is thus significantly shorter than N31—C38A, while the C33—C34, C35—C36 and C37—C38 bonds are all significantly shorter than the other peripheral C—C bonds. The two independent 4-chloro­benzoyl­methyl­ene components adopt different conformations relative to the quinoline component so that the mol­ecules have no inter­nal symmetry and hence are chiral; however, the centrosymmetric space group Pbca accommodates equal numbers of the two enantiomorphic forms.

The mol­ecules are linked into sheets by two hydrogen bonds, one each of the C—H⋯N and C—H⋯O types (Table 2[link]), and the sheet formation is readily analysed in terms of two one-dimensional substructures. Quinolinyl atom C34 in the mol­ecule at (x, y, z) acts as a hydrogen-bond donor to atom N31 in the mol­ecule at (−[{1\over 2}] + x, y, [{1\over 2}] − z), so forming a

[Scheme 1]
C(5) (Bernstein et al., 1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]) chain running parallel to the [100] direction and generated by the a-glide plane at z = [1\over4] (Fig. 2[link]). In addition, quinolinyl atom C37 in the mol­ecule at (x, y, z) acts as a hydrogen-bond donor to atom O17 in the mol­ecule at (1 − x, −[{1\over 2}] + y, [{1\over 2}] − z), so forming a C(11) chain running parallel to the [010] direction and generated by the 21 screw axis along ([1\over2], y, [1\over4]) (Fig. 3[link]).

The combination of the [100] and [010] chains generates a (001) sheet in the form of a (4,4)-net (Batten & Robson, 1998[Batten, S. R. & Robson, R. (1998). Angew. Chem. Int. Ed. 37, 1460-1494.]) built from a single type of R44(26) ring, lying in the domain −0.02 < z < 0.52, and generated by the glide plane and screw axes at z = [1\over4] (Fig. 4[link]). A second sheet, related to the first by inversion, lies in the domain 0.48 < z < 1.02, and is generated by the glide plane and screw axes at z = [3\over4].

The only direction-specific inter­action between adjacent sheets is a rather long C—H⋯O contact with aryl atom C15 as the donor (Table 2[link]) but whose H⋯O distance is close to the van der Waals limit; this inter­action is therefore probably of little or no structural significance.

The mol­ecular constitution of (I)[link] has some resemblance to that of the thienyl compound (IV)[link], but the supramolecular arrangement is entirely different in (IV)[link], where the mol­ecules are linked into cyclic centrosymmetric dimers by paired C—H⋯π(thien­yl) hydrogen bonds (Trilleras et al., 2005[Trilleras, J., Quiroga, J., Cobo, J., Low, J. N. & Glidewell, C. (2005). Acta Cryst. E61, o1892-o1894.]).

[Figure 1]
Figure 1
The mol­ecule of (I)[link], showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2]
Figure 2
Part of the crystal structure of (I)[link], showing the formation of a hydrogen-bonded C(5) chain along [100]. For the sake of clarity, H atoms not involved in the motif shown have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (−[{1\over 2}] + x, y, [{1\over 2}] − z) and ([{1\over 2}] + x, y, [{1\over 2}] − z), respectively.
[Figure 3]
Figure 3
Part of the crystal structure of (I)[link], showing the formation of a hydrogen-bonded C(11) chain along [010]. For the sake of clarity, H atoms not involved in the motif shown have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (1 − x, −[{1\over 2}] + y, [{1\over 2}] − z) and (1 − x, [{1\over 2}] + y, [{1\over 2}] − z), respectively.
[Figure 4]
Figure 4
A stereoview of part of the crystal structure of (I)[link], showing the formation of a (001) sheet built from R44(26) rings. For the sake of clarity, H atoms not involved in the motifs shown have been omitted.

Experimental

Hydrazine hydrate (0.70 g of a 55% aqueous solution, 12 mmol) was added dropwise to a solution of (E)-1-(4-chloro­phen­yl)-3-(2-chloro-quinolin-3-­yl)prop-2-en-1-one, (III)[link] (2.3 g, 7 mmol), in methanol (40 ml), and the resulting mixture was then stirred at room temperature for 15 min. The solid product was collected by filtration and washed with cold methanol to give 2-chloro-3-[3-(4-chloro­phen­yl)-1H-pyrazol-5-yl]quinoline, (II)[link] (2.2 g, 88% yield). Evaporation of the filtrate yielded crystals of (I)[link] suitable for single-crystal X-ray diffraction (yield 10%, m.p. 505–506 K). MS (EI 70 eV), m/z (%) 481 (5, M+), 328 (64, [M − ClC6H4COCH2]+), 292 (62), 139 (100).

Crystal data

  • C26H18Cl3NO2

  • Mr = 482.76

  • Orthorhombic, P b c a

  • a = 11.2405 (2) Å

  • b = 18.8738 (3) Å

  • c = 21.0529 (3) Å

  • V = 4466.39 (12) Å3

  • Z = 8

  • Dx = 1.436 Mg m−3

  • Mo Kα radiation

  • Cell parameters from 5112 reflections

  • θ = 3.4–27.5°

  • μ = 0.44 mm−1

  • T = 120 (2) K

  • Block, colourless

  • 0.20 × 0.20 × 0.15 mm
Data collection

  • Nonius KappaCCD diffractometer

  • φ and ω scans

  • Absorption correction: multi-scan(SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Version 2.10. University of Göttingen, Germany.])Tmin = 0.922, Tmax = 0.938

  • 52455 measured reflections

  • 5112 independent reflections

  • 3921 reflections with I > 2σ(I)

  • Rint = 0.048

  • θmax = 27.5°

  • h = −14 → 14

  • k = −21 → 24

  • l = −27 → 27
Refinement

  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.116

  • S = 1.05

  • 5112 reflections

  • 289 parameters

  • H-atom parameters constrained

  • w = 1/[σ2(Fo2) + (0.0554P)2 + 2.4672P] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max = 0.001

  • Δρmax = 0.41 e Å−3

  • Δρmin = −0.58 e Å−3

Table 1
Selected geometric parameters (Å, °)[link]

N31—C32 1.302 (2)
N31—C38A 1.368 (2)
C32—C33 1.422 (2)
C33—C34 1.370 (3)
C34—C34A 1.414 (3)
C34A—C35 1.418 (3)
C35—C36 1.369 (3)
C36—C37 1.402 (3)
C37—C38 1.369 (3)
C38—C38A 1.416 (3)
C34A—C38A 1.409 (3)
C32—Cl3 1.7463 (18)
C32—C33—C1—C18 −110.03 (19)
C33—C1—C18—C17 160.82 (15)
C1—C18—C17—C11 171.11 (15)
C18—C17—C11—C12 3.3 (3)
C32—C33—C1—C28 126.64 (18)
C33—C1—C28—C27 −67.55 (19)
C1—C28—C27—C21 −176.29 (15)
C28—C27—C21—C22 −16.4 (3)

Table 2
Hydrogen-bond geometry (Å, °)[link]

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C15—H15⋯O17i 0.95 2.59 3.502 (2) 160
C34—H34⋯N31ii 0.95 2.39 3.244 (2) 150
C37—H37⋯O17iii 0.95 2.45 3.330 (2) 155
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]; (ii) [x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]; (iii) -x+1, [y-{\script{1\over 2}}], [-z+{\script{1\over 2}}].

The space group Pbca was uniquely assigned from the systematic absences. All H atoms were located from difference maps and then treated as riding atoms, with C—H distances of 0.95 (aromatic), 0.99 (CH2) and 1.00 Å (aliphatic CH), and with Uiso(H) values of 1.2Ueq(C).

Data collection: COLLECT (Hooft, 1999[Hooft, R. W. W. (1999). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003[McArdle, P. (2003). OSCAIL for Windows. Version 10. Crystallography Centre, Chemistry Department, NUI Galway, Ireland.]) and SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999[Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S0108270105039193/sk1891sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S0108270105039193/sk1891Isup2.hkl


Comment top

With the aim of developing new classes of fused heterocyclic systems, we have prepared a range of novel chalcones appropriately functionalized for use as intermediates. The reactions used to prepare such chalcones involve methyl aryl ketones and aryl or heteroaryl aldehydes. We report here the structure of the title compound, (I), obtained in low yield as a by-product in the preparation of the pyrazolylquinoline (II) via the corresponding chalcone, (III), formed by the reaction between 2-chloro-3-quinolinecarbaldehyde and methyl 4-chlorophenyl ketone.

The bond distances within the quinoline portion of the molecule (Table 1) show evidence for significant bond fixation; thus the N31—C32 bond is significantly shorter than N31—C38A, while the C33—C34, C35—C36 and C37—C38 bonds are all significantly shorter than the other peripheral C—C bonds. The two independent 4-chlorobenzoylmethylene components adopt different conformations relative to the quinoline component so that the molecules have no internal symmetry and hence are chiral; however, the centrosymmetric space group Pbca accommodates equal numbers of the two enantiomorphic forms.

The molecules are linked into sheets by two hydrogen bonds, one each of C—H···N and C—H···O types (Table 2), and the sheet formation is readily analysed in terms of two one-dimensional substructures. Quinolinyl atom C34 in the molecule at (x, y, z) acts as a hydrogen-bond donor to atom N31 in the molecule at (-1/2 + x, y, 1/2 - z), so forming a C(5) (Bernstein et al., 1995) chain running parallel to the [100] direction and generated by the a-glide plane at z = 1/4 (Fig. 2). In addition, quinolinyl atom C37 in the molecule at (x, y, z) acts as a hydrogen-bond donor to atom O17 in the molecule at (1 - x, -1/2 + y, 1/2 - z), so forming a C(11) chain running parallel to the [010] direction and generated by the 21 screw axis along (1/2, y, 1/4) (Fig. 3).

The combination of the [100] and [010] chains generates a (001) sheet in the form of a (4,4)-net (Batten & Robson, 1998) built from a single type of R44(26) ring, lying in the domain -0.02 < z < 0.52, and generated by the glide plane and screw axes at z = 1/4 (Fig. 4). A second sheet, related to the first by inversion, lies in the domain 0.48 < z < 1.02 and is generated by the glide plane and screw axes at z = 3/4.

The only direction-specific interaction between adjacent sheets is a rather long C—H···O contact with the aryl atom C15 as the donor (Table 2) but whose H···O distance is close to the van der Waals limit; this interaction is therefore probably of little or no structural significance.

The molecular constitution of compound (I) has some resemblance to that of the thienyl compound (IV), but the supramolecular arrangement is entirely different in (IV), where the molecules are linked into cyclic centrosymmetric dimers by paired C—H···π(thienyl) hydrogen bonds (Trilleras et al., 2005).

Experimental top

Hydrazine hydrate (0.70 g of a 55% aqueous solution, 12 mmol) was added dropwise to a solution of (E)-1-(4-chlorophenyl)-3-(2-chloro-3-quinolinyl)-2-propen-1-one, (III) (2.3 g, 7 mmol), in methanol (40 ml), and the resulting mixture was then stirred at room temperature for 15 min. The solid product was collected by filtration and washed with cold methanol to give 2-chloro-3-[3-(4-chlorophenyl)-1H-pyrazol-5-yl]quinoline, (II) (2.2 g, 88% yield). Evaporation of the filtrate yielded crystals of (I) suitable for single-crystal X-ray diffraction (yield 10%, m.p. 505–506 K). MS (EI 70 eV), m/z (%) 481 (5, M+), 328 (64, [M-ClC6H4COCH2]+), 292?(62), 139?(100).

Refinement top

The space group Pbca was uniquely assigned from the systematic absences. All H atoms were located from difference maps, and then treated as riding atoms with C—H distances of 0.95 Å (aromatic), 0.99 Å (CH2) or 1.00 Å (aliphatic CH), and with Uiso(H) = 1.2Ueq(C).

Structure description top

With the aim of developing new classes of fused heterocyclic systems, we have prepared a range of novel chalcones appropriately functionalized for use as intermediates. The reactions used to prepare such chalcones involve methyl aryl ketones and aryl or heteroaryl aldehydes. We report here the structure of the title compound, (I), obtained in low yield as a by-product in the preparation of the pyrazolylquinoline (II) via the corresponding chalcone, (III), formed by the reaction between 2-chloro-3-quinolinecarbaldehyde and methyl 4-chlorophenyl ketone.

The bond distances within the quinoline portion of the molecule (Table 1) show evidence for significant bond fixation; thus the N31—C32 bond is significantly shorter than N31—C38A, while the C33—C34, C35—C36 and C37—C38 bonds are all significantly shorter than the other peripheral C—C bonds. The two independent 4-chlorobenzoylmethylene components adopt different conformations relative to the quinoline component so that the molecules have no internal symmetry and hence are chiral; however, the centrosymmetric space group Pbca accommodates equal numbers of the two enantiomorphic forms.

The molecules are linked into sheets by two hydrogen bonds, one each of C—H···N and C—H···O types (Table 2), and the sheet formation is readily analysed in terms of two one-dimensional substructures. Quinolinyl atom C34 in the molecule at (x, y, z) acts as a hydrogen-bond donor to atom N31 in the molecule at (-1/2 + x, y, 1/2 - z), so forming a C(5) (Bernstein et al., 1995) chain running parallel to the [100] direction and generated by the a-glide plane at z = 1/4 (Fig. 2). In addition, quinolinyl atom C37 in the molecule at (x, y, z) acts as a hydrogen-bond donor to atom O17 in the molecule at (1 - x, -1/2 + y, 1/2 - z), so forming a C(11) chain running parallel to the [010] direction and generated by the 21 screw axis along (1/2, y, 1/4) (Fig. 3).

The combination of the [100] and [010] chains generates a (001) sheet in the form of a (4,4)-net (Batten & Robson, 1998) built from a single type of R44(26) ring, lying in the domain -0.02 < z < 0.52, and generated by the glide plane and screw axes at z = 1/4 (Fig. 4). A second sheet, related to the first by inversion, lies in the domain 0.48 < z < 1.02 and is generated by the glide plane and screw axes at z = 3/4.

The only direction-specific interaction between adjacent sheets is a rather long C—H···O contact with the aryl atom C15 as the donor (Table 2) but whose H···O distance is close to the van der Waals limit; this interaction is therefore probably of little or no structural significance.

The molecular constitution of compound (I) has some resemblance to that of the thienyl compound (IV), but the supramolecular arrangement is entirely different in (IV), where the molecules are linked into cyclic centrosymmetric dimers by paired C—H···π(thienyl) hydrogen bonds (Trilleras et al., 2005).

Computing details top

Data collection: COLLECT (Hooft, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures top
[Figure 1] Fig. 1. The molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Part of the crystal structure of (I), showing the formation of a hydrogen-bonded C(5) chain along [100]. For the sake of clarity, H atoms not involved in the motif shown have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (-1/2 + x, y, 1/2 - z) and (1/2 + x, y, 1/2 - z), respectively.
[Figure 3] Fig. 3. Part of the crystal structure of (I), showing the formation of a hydrogen-bonded C(11) chain along [010]. For the sake of clarity, H atoms not involved in the motif shown have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (1 - x, -1/2 + y, 1/2 - z) and (1 - x, 1/2 + y, 1/2 - z), respectively.
[Figure 4] Fig. 4. A stereoview of part of the crystal structure of (I), showing the formation of a (001) sheet built from R44(26) rings. For the sake of clarity, H atoms not involved in the motifs shown have been omitted.
1,5-Bis(4-chlorophenyl)-3-(2-chloroquinolin-3-yl)pentane-1,5-dione top
Crystal data top
C26H18Cl3NO2F(000) = 1984
Mr = 482.76Dx = 1.436 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 5112 reflections
a = 11.2405 (2) Åθ = 3.4–27.5°
b = 18.8738 (3) ŵ = 0.44 mm−1
c = 21.0529 (3) ÅT = 120 K
V = 4466.39 (12) Å3Block, colourless
Z = 80.20 × 0.20 × 0.15 mm
Data collection top
Nonius KappaCCD
diffractometer		5112 independent reflections
Radiation source: Bruker-Nonius FR91 rotating anode3921 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.4°
φ and ω scansh = −14→14
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		k = −21→24
Tmin = 0.922, Tmax = 0.938l = −27→27
52455 measured reflections
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0554P)2 + 2.4672P]
where P = (Fo2 + 2Fc2)/3
5112 reflections(Δ/σ)max = 0.001
289 parametersΔρmax = 0.41 e Å−3
0 restraintsΔρmin = −0.58 e Å−3
Crystal data top
C26H18Cl3NO2V = 4466.39 (12) Å3
Mr = 482.76Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 11.2405 (2) ŵ = 0.44 mm−1
b = 18.8738 (3) ÅT = 120 K
c = 21.0529 (3) Å0.20 × 0.20 × 0.15 mm
Data collection top
Nonius KappaCCD
diffractometer		5112 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		3921 reflections with I > 2σ(I)
Tmin = 0.922, Tmax = 0.938Rint = 0.048
52455 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.116H-atom parameters constrained
S = 1.05Δρmax = 0.41 e Å−3
5112 reflectionsΔρmin = −0.58 e Å−3
289 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl1−0.24463 (5)0.60892 (4)0.52239 (3)0.05197 (19)
Cl20.36147 (7)0.93210 (3)0.02585 (3)0.05640 (19)
Cl30.63263 (4)0.59715 (3)0.37707 (2)0.03324 (13)
O170.27494 (12)0.71370 (7)0.40277 (7)0.0345 (3)
O270.55516 (11)0.70553 (8)0.24637 (7)0.0389 (3)
N310.64154 (13)0.49686 (8)0.29422 (7)0.0261 (3)
C10.38694 (15)0.62862 (9)0.31345 (9)0.0248 (4)
C110.10666 (16)0.64331 (10)0.42440 (8)0.0254 (4)
C120.04763 (17)0.57904 (11)0.41819 (10)0.0333 (4)
C13−0.06099 (18)0.56808 (13)0.44833 (10)0.0398 (5)
C14−0.10900 (17)0.62233 (12)0.48422 (9)0.0349 (5)
C15−0.05275 (17)0.68684 (11)0.49112 (9)0.0328 (4)
C160.05558 (17)0.69703 (10)0.46129 (8)0.0281 (4)
C170.22362 (16)0.65811 (9)0.39326 (8)0.0250 (4)
C180.27700 (16)0.60194 (10)0.35018 (9)0.0262 (4)
C210.42731 (16)0.76794 (10)0.17734 (9)0.0273 (4)
C220.31889 (17)0.77041 (10)0.14542 (9)0.0308 (4)
C230.29949 (19)0.81983 (11)0.09786 (10)0.0354 (4)
C240.3877 (2)0.86827 (11)0.08384 (10)0.0362 (5)
C250.49545 (19)0.86799 (11)0.11552 (10)0.0367 (5)
C260.51556 (17)0.81716 (10)0.16177 (9)0.0317 (4)
C270.45339 (16)0.71555 (10)0.22867 (9)0.0281 (4)
C280.34994 (15)0.67711 (10)0.25885 (9)0.0257 (4)
C320.57374 (15)0.54819 (10)0.31410 (8)0.0245 (4)
C330.45995 (15)0.56650 (9)0.28962 (8)0.0237 (4)
C340.41842 (16)0.52346 (10)0.24216 (9)0.0273 (4)
C34A0.48628 (15)0.46580 (10)0.21923 (8)0.0256 (4)
C350.44493 (17)0.41947 (11)0.17103 (9)0.0324 (4)
C360.5168 (2)0.36569 (11)0.15028 (9)0.0363 (5)
C370.63176 (18)0.35695 (11)0.17500 (10)0.0340 (4)
C380.67301 (17)0.40008 (10)0.22242 (9)0.0309 (4)
C38A0.59988 (16)0.45523 (9)0.24592 (9)0.0249 (4)
H10.43740.65670.34340.030*
H120.08160.54230.39320.040*
H13−0.10140.52410.44430.048*
H15−0.08770.72350.51580.039*
H160.09580.74100.46590.034*
H18A0.21590.58620.31940.031*
H18B0.30000.56040.37620.031*
H220.25770.73790.15630.037*
H230.22640.82040.07520.042*
H250.55480.90210.10570.044*
H260.59000.81570.18310.038*
H28A0.30920.64850.22600.031*
H28B0.29230.71250.27500.031*
H340.34240.53260.22420.033*
H350.36790.42570.15330.039*
H360.48850.33390.11870.044*
H370.68160.32060.15860.041*
H380.75030.39300.23950.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0292 (3)0.0918 (5)0.0349 (3)−0.0112 (3)0.0084 (2)−0.0205 (3)
Cl20.0897 (5)0.0385 (3)0.0410 (3)−0.0038 (3)−0.0036 (3)0.0106 (2)
Cl30.0315 (2)0.0374 (3)0.0308 (2)−0.00001 (19)−0.00860 (19)−0.0048 (2)
O170.0409 (8)0.0270 (7)0.0357 (7)−0.0066 (6)0.0084 (6)−0.0057 (6)
O270.0219 (7)0.0454 (9)0.0493 (9)0.0002 (6)0.0007 (6)0.0106 (7)
N310.0236 (7)0.0283 (8)0.0263 (8)0.0010 (6)0.0026 (6)0.0037 (6)
C10.0222 (8)0.0248 (9)0.0275 (9)−0.0001 (7)0.0012 (7)−0.0046 (7)
C110.0263 (9)0.0294 (10)0.0205 (8)0.0037 (7)0.0003 (7)0.0000 (7)
C120.0313 (10)0.0364 (11)0.0321 (10)−0.0030 (8)0.0044 (8)−0.0086 (8)
C130.0332 (11)0.0493 (13)0.0369 (11)−0.0126 (9)0.0062 (9)−0.0120 (10)
C140.0246 (9)0.0575 (14)0.0227 (9)−0.0008 (9)0.0004 (7)−0.0055 (9)
C150.0332 (10)0.0444 (12)0.0207 (9)0.0126 (9)−0.0002 (7)−0.0016 (8)
C160.0338 (10)0.0296 (10)0.0209 (9)0.0064 (8)−0.0004 (7)0.0019 (7)
C170.0288 (9)0.0234 (9)0.0229 (9)0.0013 (7)−0.0003 (7)0.0002 (7)
C180.0263 (9)0.0250 (9)0.0274 (9)−0.0015 (7)0.0028 (7)−0.0025 (7)
C210.0276 (9)0.0271 (10)0.0273 (9)0.0022 (7)0.0073 (7)−0.0038 (7)
C220.0307 (10)0.0278 (10)0.0339 (10)−0.0003 (8)0.0021 (8)−0.0015 (8)
C230.0397 (11)0.0328 (11)0.0336 (10)0.0041 (9)−0.0026 (9)−0.0017 (8)
C240.0527 (13)0.0283 (10)0.0276 (10)0.0048 (9)0.0068 (9)−0.0011 (8)
C250.0436 (12)0.0298 (11)0.0367 (11)−0.0038 (9)0.0167 (9)−0.0044 (9)
C260.0295 (9)0.0321 (11)0.0335 (10)−0.0003 (8)0.0105 (8)−0.0043 (8)
C270.0236 (9)0.0294 (10)0.0313 (10)0.0008 (7)0.0033 (7)−0.0040 (8)
C280.0211 (8)0.0268 (9)0.0290 (9)0.0010 (7)0.0015 (7)−0.0009 (7)
C320.0231 (9)0.0266 (9)0.0238 (9)−0.0049 (7)0.0000 (7)0.0012 (7)
C330.0201 (8)0.0249 (9)0.0261 (9)0.0003 (7)0.0036 (7)−0.0007 (7)
C340.0223 (8)0.0298 (10)0.0300 (9)−0.0004 (7)−0.0011 (7)−0.0036 (8)
C34A0.0252 (9)0.0269 (9)0.0247 (9)−0.0017 (7)0.0045 (7)−0.0004 (7)
C350.0340 (10)0.0337 (11)0.0294 (10)−0.0011 (8)0.0005 (8)−0.0051 (8)
C360.0482 (12)0.0325 (11)0.0280 (10)−0.0021 (9)0.0071 (9)−0.0049 (8)
C370.0418 (11)0.0271 (10)0.0331 (10)0.0067 (8)0.0132 (9)0.0015 (8)
C380.0310 (9)0.0302 (10)0.0314 (10)0.0056 (8)0.0072 (8)0.0046 (8)
C38A0.0257 (9)0.0243 (9)0.0248 (9)−0.0001 (7)0.0055 (7)0.0047 (7)
Geometric parameters (Å, º) top
C1—C331.516 (2)C24—C251.383 (3)
C1—C281.527 (3)C24—Cl21.740 (2)
C1—C181.542 (2)C25—C261.385 (3)
C1—H11.00C25—H250.95
C11—C121.389 (3)C26—H260.95
C11—C161.400 (2)C27—O271.218 (2)
C11—C171.495 (2)C27—C281.511 (2)
C12—C131.391 (3)C28—H28A0.99
C12—H120.95C28—H28B0.99
C13—C141.382 (3)N31—C321.302 (2)
C13—H130.95N31—C38A1.368 (2)
C14—C151.380 (3)C32—C331.422 (2)
C14—Cl11.742 (2)C33—C341.370 (3)
C15—C161.384 (3)C34—C34A1.414 (3)
C15—H150.95C34A—C351.418 (3)
C16—H160.95C35—C361.369 (3)
C17—O171.214 (2)C36—C371.402 (3)
C17—C181.519 (2)C37—C381.369 (3)
C18—H18A0.99C38—C38A1.416 (3)
C18—H18B0.99C34A—C38A1.409 (3)
C21—C221.392 (3)C32—Cl31.7463 (18)
C21—C261.398 (3)C34—H340.95
C21—C271.494 (3)C35—H350.95
C22—C231.386 (3)C36—H360.95
C22—H220.95C37—H370.95
C23—C241.381 (3)C38—H380.95
C23—H230.95
C33—C1—C28111.21 (15)C25—C24—Cl2119.31 (17)
C33—C1—C18110.30 (15)C24—C25—C26118.99 (19)
C28—C1—C18110.79 (14)C24—C25—H25120.5
C33—C1—H1108.1C26—C25—H25120.5
C28—C1—H1108.1C25—C26—C21120.61 (19)
C18—C1—H1108.1C25—C26—H26119.7
C12—C11—C16119.25 (17)C21—C26—H26119.7
C12—C11—C17122.82 (16)O27—C27—C21120.57 (17)
C16—C11—C17117.93 (16)O27—C27—C28121.31 (17)
C11—C12—C13120.42 (18)C21—C27—C28118.11 (15)
C11—C12—H12119.8C27—C28—C1113.25 (14)
C13—C12—H12119.8C27—C28—H28A108.9
C14—C13—C12118.8 (2)C1—C28—H28A108.9
C14—C13—H13120.6C27—C28—H28B108.9
C12—C13—H13120.6C1—C28—H28B108.9
C15—C14—C13122.17 (18)H28A—C28—H28B107.7
C15—C14—Cl1118.74 (16)C32—N31—C38A117.79 (15)
C13—C14—Cl1119.09 (17)N31—C32—C33126.24 (17)
C14—C15—C16118.57 (18)N31—C32—Cl3114.58 (13)
C14—C15—H15120.7C33—C32—Cl3119.18 (14)
C16—C15—H15120.7C34—C33—C32115.27 (16)
C15—C16—C11120.79 (18)C34—C33—C1121.02 (16)
C15—C16—H16119.6C32—C33—C1123.71 (16)
C11—C16—H16119.6C33—C34—C34A121.44 (17)
O17—C17—C11120.47 (16)C33—C34—H34119.3
O17—C17—C18120.93 (16)C34A—C34—H34119.3
C11—C17—C18118.60 (15)C38A—C34A—C34117.50 (17)
C17—C18—C1112.83 (15)C38A—C34A—C35119.68 (17)
C17—C18—H18A109.0C34—C34A—C35122.82 (17)
C1—C18—H18A109.0C36—C35—C34A119.47 (18)
C17—C18—H18B109.0C36—C35—H35120.3
C1—C18—H18B109.0C34A—C35—H35120.3
H18A—C18—H18B107.8C35—C36—C37120.83 (19)
C22—C21—C26119.05 (18)C35—C36—H36119.6
C22—C21—C27122.89 (17)C37—C36—H36119.6
C26—C21—C27118.05 (17)C38—C37—C36120.85 (18)
C23—C22—C21120.60 (18)C38—C37—H37119.6
C23—C22—H22119.7C36—C37—H37119.6
C21—C22—H22119.7C37—C38—C38A119.69 (18)
C24—C23—C22119.16 (19)C37—C38—H38120.2
C24—C23—H23120.4C38A—C38—H38120.2
C22—C23—H23120.4N31—C38A—C34A121.68 (16)
C23—C24—C25121.56 (19)N31—C38A—C38118.91 (17)
C23—C24—Cl2119.12 (17)C34A—C38A—C38119.41 (17)
C16—C11—C12—C13−0.1 (3)C27—C21—C26—C25−178.58 (17)
C17—C11—C12—C13179.87 (19)C22—C21—C27—O27165.11 (19)
C11—C12—C13—C140.3 (3)C26—C21—C27—O27−16.0 (3)
C12—C13—C14—C150.0 (3)C26—C21—C27—C28162.49 (16)
C12—C13—C14—Cl1−179.73 (16)O27—C27—C28—C12.2 (3)
C13—C14—C15—C16−0.4 (3)C18—C1—C28—C27169.40 (15)
Cl1—C14—C15—C16179.32 (14)C38A—N31—C32—C33−1.2 (3)
C14—C15—C16—C110.6 (3)C38A—N31—C32—Cl3178.55 (12)
C12—C11—C16—C15−0.3 (3)N31—C32—C33—C342.5 (3)
C17—C11—C16—C15179.70 (16)Cl3—C32—C33—C34−177.30 (14)
C12—C11—C17—O17−176.07 (18)N31—C32—C33—C1−177.86 (17)
C16—C11—C17—O173.9 (3)Cl3—C32—C33—C12.4 (2)
C16—C11—C17—C18−176.70 (16)C28—C1—C33—C34−53.7 (2)
O17—C17—C18—C1−9.5 (2)C18—C1—C33—C3469.6 (2)
C32—C33—C1—C18−110.03 (19)C32—C33—C34—C34A−0.9 (3)
C33—C1—C18—C17160.82 (15)C1—C33—C34—C34A179.43 (16)
C1—C18—C17—C11171.11 (15)C33—C34—C34A—C38A−1.6 (3)
C18—C17—C11—C123.3 (3)C33—C34—C34A—C35178.77 (18)
C32—C33—C1—C28126.64 (18)C38A—C34A—C35—C36−1.1 (3)
C33—C1—C28—C27−67.55 (19)C34—C34A—C35—C36178.56 (18)
C1—C28—C27—C21−176.29 (15)C34A—C35—C36—C37−1.6 (3)
C28—C27—C21—C22−16.4 (3)C35—C36—C37—C382.8 (3)
C28—C1—C18—C17−75.61 (19)C36—C37—C38—C38A−1.4 (3)
C26—C21—C22—C231.5 (3)C32—N31—C38A—C34A−1.6 (3)
C27—C21—C22—C23−179.62 (18)C32—N31—C38A—C38178.55 (16)
C21—C22—C23—C24−2.1 (3)C34—C34A—C38A—N313.0 (3)
C22—C23—C24—C250.9 (3)C35—C34A—C38A—N31−177.39 (17)
C22—C23—C24—Cl2−177.98 (15)C34—C34A—C38A—C38−177.21 (17)
C23—C24—C25—C260.9 (3)C35—C34A—C38A—C382.4 (3)
Cl2—C24—C25—C26179.80 (15)C37—C38—C38A—N31178.63 (17)
C24—C25—C26—C21−1.6 (3)C37—C38—C38A—C34A−1.2 (3)
C22—C21—C26—C250.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15···O17i0.952.593.502 (2)160
C34—H34···N31ii0.952.393.244 (2)150
C37—H37···O17iii0.952.453.330 (2)155
Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) x−1/2, y, −z+1/2; (iii) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formulaC26H18Cl3NO2
Mr482.76
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)120
a, b, c (Å)11.2405 (2), 18.8738 (3), 21.0529 (3)
V (Å3)4466.39 (12)
Z8
Radiation typeMo Kα
µ (mm−1)0.44
Crystal size (mm)0.20 × 0.20 × 0.15
Data collection
DiffractometerNonius KappaCCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.922, 0.938
No. of measured, independent and
observed [I > 2σ(I)] reflections		52455, 5112, 3921
Rint0.048
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.116, 1.05
No. of reflections5112
No. of parameters289
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.41, −0.58

Computer programs: COLLECT (Hooft, 1999), DENZO (Otwinowski & Minor, 1997) and COLLECT, DENZO and COLLECT, OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997), OSCAIL and SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 and PRPKAPPA (Ferguson, 1999).

Selected geometric parameters (Å, º) top
N31—C321.302 (2)C35—C361.369 (3)
N31—C38A1.368 (2)C36—C371.402 (3)
C32—C331.422 (2)C37—C381.369 (3)
C33—C341.370 (3)C38—C38A1.416 (3)
C34—C34A1.414 (3)C34A—C38A1.409 (3)
C34A—C351.418 (3)C32—Cl31.7463 (18)
C32—C33—C1—C18−110.03 (19)C32—C33—C1—C28126.64 (18)
C33—C1—C18—C17160.82 (15)C33—C1—C28—C27−67.55 (19)
C1—C18—C17—C11171.11 (15)C1—C28—C27—C21−176.29 (15)
C18—C17—C11—C123.3 (3)C28—C27—C21—C22−16.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15···O17i0.952.593.502 (2)160
C34—H34···N31ii0.952.393.244 (2)150
C37—H37···O17iii0.952.453.330 (2)155
Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) x−1/2, y, −z+1/2; (iii) −x+1, y−1/2, −z+1/2.
 

Acknowledgements

X-ray data were collected at the EPSRC X-ray Crystallographic Service, University of Southampton, England. JC thanks the Consejería de Innovación, Ciencia y Empresa (Junta de Andalucía, Spain) and the Universidad de Jaén for financial support. BI and HT thank COLCIENCIAS, UNIVALLE (Universidad del Valle, Colombia) and Universidad Nacional de Colombia for financial support.

References

First citationBatten, S. R. & Robson, R. (1998). Angew. Chem. Int. Ed. 37, 1460–1494.  Web of Science CrossRef Google Scholar
 First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
 First citationFerguson, G. (1999). PRPKAPPA. University of Guelph, Canada.  Google Scholar
 First citationHooft, R. W. W. (1999). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
 First citationMcArdle, P. (2003). OSCAIL for Windows. Version 10. Crystallography Centre, Chemistry Department, NUI Galway, Ireland.  Google Scholar
 First citationOtwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.  Google Scholar
 First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2003). SADABS. Version 2.10. University of Göttingen, Germany.  Google Scholar
 First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationTrilleras, J., Quiroga, J., Cobo, J., Low, J. N. & Glidewell, C. (2005). Acta Cryst. E61, o1892–o1894.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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Journal logoSTRUCTURAL
CHEMISTRY
ISSN: 2053-2296
Volume 62| Part 1| January 2006| Pages o39-o41
doi:10.1107/S0108270105039193
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