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ISSN: 2056-9890

2-Chloro-8,8-di­methyl-8,9-di­hydro-7H-chromeno[2,3-b]quinoline-10,12-dione

aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and bIndustrial Chemistry Laboratory, Central Leather Research Institute, Adyar, Chennai 600 020, India
*Correspondence e-mail: shirai2011@gmail.com

(Received 4 January 2013; accepted 11 January 2013; online 19 January 2013)

The asymmetric unit of the title compound, C18H14ClNO3, contains two independent mol­ecules (A and B). In both mol­ecules, the cyclo­hexa­none ring has a chair conformation. The dihedral angles between the pyran ring and the pyridine and chloro­phenyl rings are 2.13 (9) and 2.19 (9)°, respectively, in A, and 0.82 (9) and 1.93 (9)°, respectively, in B. The carbonyl O atoms deviate from the pyran and benzene rings to which they are attached by −0.092 (2) and 0.064 (2) Å, respectively, in A, and by −0.080 (2) and −0.063 (2) Å, respectively, in B. In the crystal, the A mol­ecules are linked via C—H⋯O hydrogen bonds, forming double-stranded chains along [100]. They lie parallel to the double-stranded chains formed by the B mol­ecules, which are also linked via C—H⋯O hydrogen bonds. The chains stack up the c axis in an –AABBAA– manner, with a number of ππ inter­actions involving A and B mol­ecules; the centroid–centroid distances vary from 3.4862 (11) to 3.6848 (11) Å

Related literature

For the uses and biological importance of diketones, see: Bennett et al. (1999[Bennett, I., Broom, N. J. P., Cassels, R., Elder, J. S., Masson, N. D. & O'Hanlon, P. J. (1999). Bioorg. Med. Chem. Lett. 9, 1847-1852.]); Sato et al. (2008[Sato, K., Yamazoe, S., Yamamoto, R., Ohata, S., Tarui, A., Omote, M., Kumadaki, I. & Ando, A. (2008). Org. Lett. 10, 2405-2408.]). For a related structure, see: Öztürk Yildirim et al. (2012[Öztürk Yildirim, S., Butcher, R. J., El-Khouly, A., Safak, C. & Şimsek, R. (2012). Acta Cryst. E68, o3365-o3366.]).

[Scheme 1]

Experimental

Crystal data
  • C18H14ClNO3

  • Mr = 327.75

  • Triclinic, [P \overline 1]

  • a = 11.4135 (4) Å

  • b = 11.6663 (5) Å

  • c = 13.5810 (6) Å

  • α = 69.265 (3)°

  • β = 73.868 (2)°

  • γ = 64.998 (5)°

  • V = 1515.11 (12) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.27 mm−1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.924, Tmax = 0.949

  • 26747 measured reflections

  • 7488 independent reflections

  • 5384 reflections with I > 2σ(I)

  • Rint = 0.033

Refinement
  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.167

  • S = 0.99

  • 7488 reflections

  • 419 parameters

  • H-atom parameters constrained

  • Δρmax = 0.27 e Å−3

  • Δρmin = −0.33 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C2—H2⋯O3i 0.93 2.33 3.255 (3) 174
C2′—H2′⋯O3′i 0.93 2.38 3.309 (3) 173
Symmetry code: (i) x+1, y-1, z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, 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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Diketones are popular in organic synthesis for their applications in biology and medicine. They are known to exhibit antioxidants, antitumour and antibacterial activities (Bennett et al., 1999). They are also key intermediates in the preparation of various heterocyclic compounds (Sato et al., 2008). The synthesis and crystal structure of the title diketone is reported on herein.

The asymmetric unit of the title compound contains two independent molecules (A and B), as illustrated in Fig. 1. In both molecules the cyclohexanone ring [(C11-C1) in A and (C11'-C16') in B] has a chair conformation. In molecule A the dihedral angle between the pyran ring (O2/C4-C9) and the pyridine ring (N1/C8-C12) is 2.13 (9)°. The dihedral angle between the pyran ring and the phenyl ring (C11-C16) is 4.11 (10)° and the dihedral angle between the pyran ring and the chlorophenyl ring (C1-C6) is 2.19 (9)°. In molecule B the dihedral angle between the pyran ring (O2'/C4'-C9') and the pyridine ring (N1'/C8'-C12') is 0.82 (9)°. The dihedral angle between the pyran ring and the phenyl ring (C11'-C16') is 8.21 (10)° and the dihedral angle between the pyran ring and the chlorophenyl ring (C1'-C6') is 1.93 (9)°.

In molecule A the carbonyl oxygen atoms O1 and O3 attached to the pyran ring (O2/C4-C9) and the phenyl ring (C11-C16) deviate by -0.0915 (22)Å and 0.0643 (24)Å, respectively. In molecule B the carbonyl oxygen atoms O1' and O3' attached to the pyran ring (O2'/C4'-C9') and the phenyl ring (C11'-C16') deviate by -0.096 (2) Å and -0.063 (2) Å, respectively.

In A the pyridine ring makes a dihedral angle of 6.23 (10)° with the phenyl ring and a dihedral angle of 4.31 (10)° with the chlorophenyl ring. In B the pyridine ring makes a dihedral angle of 8.85 (10)° with the phenyl ring and a dihedral angle of 2.42 (10)° with the chloro phenyl ring. The chlorine atoms Cl1 and Cl1' deviated by -0.0423 (8) Å and 0.0598 (8) Å, respectively, from the phenyl ring to which they are attached.

In the crystal, the A molecules are linked via C-H···O hydrogen bonds to form chains along the a axis. They lie parallel to the chains formed by the B molecules which are also linked via C-H···O hydrogen bonds (Table 1 and Fig. 2). The A and B molecules are also linked via a number of π-π interactions; these include Cg1···Cg3i 3.4969 (11) Å; Cg1···Cg11 3.4862 (11) Å; Cg2···Cg11 3.6727 (11) Å; Cg2···Cg12 3.6848 (11) Å; Cg11···Cg13i 3.5101 (11) Å; symmetry code: (i) -x+1, -y+1, -z; where Cg1, Cg2, Cg3, Cg11, Cg12, Cg13 are the centroids of rings O2/C4-C9, N1/C8-C12, C1-C6, O2'/C4'-C9', N1'/C9'-C12' and C1'-C6', respectively.

Related literature top

For the uses and biological importance of diketones, see: Bennett et al. (1999); Sato et al. (2008). For a related structure, see: Öztürk Yildirim et al. (2012).

Experimental top

2-Amino-4-oxo-4H-chromene-3-carbaldehyde ( 100 mg, 1 mmol) was reacted with 5,5-dimethylcyclohexane-1,3-dione( 88 mg, 1.2 mmol) in the presence of yeterbium triflate [Yb(oft)3] (98 mg, 0.3 mmol) after stirring. All the reactants were dissolved in xylene (5 ml). The reaction mixture was refluxed at 398 K for 12 hours. The reaction mixture was extracted with ethyl acetate/Hexane 40:60 (v/v). The completion of the reaction was monitored by TLC. The final product was purified by column chromatography (ethyl acetate/hexane) giving the pure title compound [Yield = 80%]. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.

Refinement top

The hydrogen atoms were placed in calculated positions and treated as riding atoms: C—H = 0.93 Å to 0.97 Å, with Uiso(H) = 1.5Ueq(C) for methyl H atoms and = 1.2Ueq(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 (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the two independent molecules (A and B) of the title compound, showing the atom numbering. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. The crystal packing of the title compound viewed along the b axis. H-atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity.
2-Chloro-8,8-dimethyl-8,9-dihydro-7H-chromeno[2,3-b]quinoline- 10,12-dione top
Crystal data top
C18H14ClNO3Z = 4
Mr = 327.75F(000) = 680
Triclinic, P1Dx = 1.437 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.4135 (4) ÅCell parameters from 7488 reflections
b = 11.6663 (5) Åθ = 1.6–28.4°
c = 13.5810 (6) ŵ = 0.27 mm1
α = 69.265 (3)°T = 293 K
β = 73.868 (2)°Block, colourless
γ = 64.998 (5)°0.30 × 0.25 × 0.20 mm
V = 1515.11 (12) Å3
Data collection top
Bruker SMART APEXII area-detector
diffractometer
7488 independent reflections
Radiation source: fine-focus sealed tube5384 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
ω and ϕ scansθmax = 28.4°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 1514
Tmin = 0.924, Tmax = 0.949k = 1515
26747 measured 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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0783P)2 + 0.7873P]
where P = (Fo2 + 2Fc2)/3
7488 reflections(Δ/σ)max < 0.001
419 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.33 e Å3
Crystal data top
C18H14ClNO3γ = 64.998 (5)°
Mr = 327.75V = 1515.11 (12) Å3
Triclinic, P1Z = 4
a = 11.4135 (4) ÅMo Kα radiation
b = 11.6663 (5) ŵ = 0.27 mm1
c = 13.5810 (6) ÅT = 293 K
α = 69.265 (3)°0.30 × 0.25 × 0.20 mm
β = 73.868 (2)°
Data collection top
Bruker SMART APEXII area-detector
diffractometer
7488 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
5384 reflections with I > 2σ(I)
Tmin = 0.924, Tmax = 0.949Rint = 0.033
26747 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.167H-atom parameters constrained
S = 0.99Δρmax = 0.27 e Å3
7488 reflectionsΔρmin = 0.33 e Å3
419 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C10.5452 (2)0.2391 (2)0.17141 (17)0.0507 (5)
C1'0.7356 (2)0.4947 (2)0.32726 (17)0.0547 (5)
C20.6544 (2)0.2742 (2)0.14200 (17)0.0528 (5)
H20.73760.20980.13890.063*
C2'0.7043 (2)0.3837 (2)0.35361 (17)0.0558 (6)
H2'0.77030.30190.35520.067*
C3'0.5750 (2)0.3948 (2)0.37743 (17)0.0525 (5)
H3'0.55320.32090.39510.063*
C30.64025 (19)0.4033 (2)0.11754 (17)0.0492 (5)
H30.71350.42710.09730.059*
C40.51544 (18)0.4985 (2)0.12322 (14)0.0411 (4)
C4'0.4777 (2)0.51767 (19)0.37477 (15)0.0432 (4)
C50.40526 (18)0.4646 (2)0.15103 (15)0.0422 (4)
C5'0.5084 (2)0.62854 (19)0.35132 (15)0.0435 (4)
C6'0.6394 (2)0.6162 (2)0.32709 (17)0.0511 (5)
H6'0.66170.68950.31090.061*
C60.4216 (2)0.3327 (2)0.17485 (17)0.0489 (5)
H60.34900.30830.19300.059*
C7'0.4033 (2)0.75624 (19)0.35395 (16)0.0448 (4)
C70.27378 (19)0.5668 (2)0.15261 (17)0.0458 (5)
C80.27349 (17)0.6992 (2)0.13091 (15)0.0401 (4)
C8'0.27101 (19)0.75360 (18)0.37550 (14)0.0386 (4)
C90.38973 (17)0.7232 (2)0.10728 (14)0.0395 (4)
C9'0.25063 (19)0.63696 (18)0.39621 (15)0.0403 (4)
C100.15855 (18)0.8078 (2)0.13264 (16)0.0431 (4)
H100.07820.79810.14660.052*
C10'0.15975 (19)0.86517 (18)0.37749 (15)0.0406 (4)
H10'0.16750.94570.36450.049*
C110.16353 (18)0.9292 (2)0.11373 (16)0.0433 (4)
C11'0.0377 (2)0.85759 (19)0.39857 (16)0.0419 (4)
C120.28618 (19)0.9417 (2)0.09298 (16)0.0452 (4)
C12'0.0290 (2)0.73483 (19)0.41838 (16)0.0443 (4)
C130.2948 (2)1.0714 (2)0.0769 (2)0.0595 (6)
H13A0.37441.07580.02880.071*
H13B0.30091.07740.14460.071*
C13'0.1015 (2)0.7213 (2)0.4426 (2)0.0604 (6)
H13C0.09450.63450.48970.072*
H13D0.12560.72860.37700.072*
C140.1788 (2)1.1890 (2)0.0318 (2)0.0574 (6)
C14'0.2096 (2)0.8249 (2)0.4948 (2)0.0547 (5)
C15'0.2116 (2)0.9614 (2)0.4250 (2)0.0583 (6)
H15A0.23990.97860.35840.070*
H15B0.27531.02670.46060.070*
C150.0525 (2)1.1739 (2)0.1015 (2)0.0668 (7)
H15C0.04771.18320.17090.080*
H15D0.02141.24460.06970.080*
C160.0408 (2)1.0454 (2)0.1164 (2)0.0532 (5)
C16'0.0816 (2)0.97710 (19)0.40067 (17)0.0470 (5)
C170.1858 (3)1.3168 (3)0.0318 (3)0.0908 (11)
H17A0.26781.32350.00770.136*
H17B0.17891.31720.10380.136*
H17C0.11531.39000.00070.136*
C17'0.3419 (3)0.8143 (3)0.5042 (3)0.0808 (9)
H17D0.40980.87930.53680.121*
H17E0.34000.72830.54720.121*
H17F0.35860.82860.43450.121*
C180.1796 (3)1.1930 (3)0.0825 (2)0.0802 (8)
H18A0.25881.20240.12610.120*
H18B0.10581.26630.11020.120*
H18C0.17461.11300.08260.120*
C18'0.1844 (2)0.8035 (3)0.6060 (2)0.0637 (6)
H18D0.25420.86740.63860.096*
H18E0.10310.81290.60040.096*
H18F0.18030.71680.64870.096*
N10.39826 (15)0.83855 (18)0.08958 (14)0.0470 (4)
N1'0.13495 (18)0.62525 (16)0.41741 (14)0.0474 (4)
O10.17423 (15)0.54410 (18)0.16973 (18)0.0723 (5)
O1'0.42395 (16)0.85595 (16)0.33981 (16)0.0663 (5)
O2'0.35174 (14)0.52027 (13)0.39693 (12)0.0485 (3)
O20.50909 (12)0.62565 (14)0.10098 (11)0.0463 (3)
O30.06431 (15)1.03402 (18)0.13335 (19)0.0777 (6)
O3'0.07287 (16)1.08344 (15)0.38172 (16)0.0648 (5)
Cl1'0.89836 (6)0.48087 (7)0.29361 (6)0.0808 (2)
Cl10.56258 (7)0.07546 (6)0.20440 (6)0.0733 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0506 (12)0.0466 (11)0.0461 (11)0.0068 (9)0.0091 (9)0.0145 (9)
C1'0.0457 (11)0.0560 (13)0.0444 (11)0.0033 (10)0.0101 (9)0.0091 (9)
C20.0416 (11)0.0522 (12)0.0490 (12)0.0025 (9)0.0083 (9)0.0185 (10)
C2'0.0551 (13)0.0442 (11)0.0447 (11)0.0062 (10)0.0117 (9)0.0120 (9)
C3'0.0608 (13)0.0367 (10)0.0450 (11)0.0027 (9)0.0093 (9)0.0112 (8)
C30.0332 (9)0.0575 (13)0.0469 (11)0.0066 (9)0.0038 (8)0.0166 (9)
C40.0350 (9)0.0468 (11)0.0336 (9)0.0076 (8)0.0048 (7)0.0110 (8)
C4'0.0483 (11)0.0365 (10)0.0341 (9)0.0051 (8)0.0065 (8)0.0097 (7)
C50.0338 (9)0.0493 (11)0.0369 (9)0.0075 (8)0.0043 (7)0.0141 (8)
C5'0.0464 (11)0.0370 (10)0.0361 (9)0.0053 (8)0.0077 (8)0.0083 (7)
C6'0.0470 (11)0.0468 (11)0.0470 (11)0.0082 (9)0.0095 (9)0.0073 (9)
C60.0449 (11)0.0517 (12)0.0473 (11)0.0138 (9)0.0056 (9)0.0157 (9)
C7'0.0469 (11)0.0342 (10)0.0457 (11)0.0085 (8)0.0088 (8)0.0082 (8)
C70.0339 (9)0.0511 (11)0.0497 (11)0.0112 (8)0.0024 (8)0.0184 (9)
C80.0304 (8)0.0490 (11)0.0378 (9)0.0102 (8)0.0050 (7)0.0136 (8)
C8'0.0450 (10)0.0310 (9)0.0356 (9)0.0095 (8)0.0058 (7)0.0097 (7)
C90.0274 (8)0.0468 (10)0.0374 (9)0.0075 (7)0.0050 (7)0.0107 (8)
C9'0.0474 (10)0.0304 (9)0.0375 (9)0.0086 (8)0.0046 (8)0.0111 (7)
C100.0287 (8)0.0523 (11)0.0471 (11)0.0125 (8)0.0043 (7)0.0156 (9)
C10'0.0469 (10)0.0277 (8)0.0429 (10)0.0105 (8)0.0068 (8)0.0082 (7)
C110.0306 (9)0.0465 (11)0.0479 (11)0.0087 (8)0.0063 (7)0.0131 (9)
C11'0.0445 (10)0.0338 (9)0.0436 (10)0.0110 (8)0.0059 (8)0.0106 (8)
C120.0341 (9)0.0500 (11)0.0473 (11)0.0127 (8)0.0071 (8)0.0108 (9)
C12'0.0477 (11)0.0365 (10)0.0477 (11)0.0134 (8)0.0038 (8)0.0150 (8)
C130.0414 (11)0.0538 (13)0.0837 (17)0.0162 (10)0.0119 (11)0.0185 (12)
C13'0.0535 (13)0.0485 (12)0.0853 (17)0.0205 (10)0.0039 (12)0.0276 (12)
C140.0433 (11)0.0438 (11)0.0814 (16)0.0128 (9)0.0082 (11)0.0174 (11)
C14'0.0394 (10)0.0427 (11)0.0792 (16)0.0130 (9)0.0093 (10)0.0153 (11)
C15'0.0441 (11)0.0435 (11)0.0791 (16)0.0095 (9)0.0169 (11)0.0091 (11)
C150.0426 (12)0.0531 (14)0.100 (2)0.0092 (10)0.0002 (12)0.0335 (13)
C160.0349 (10)0.0497 (12)0.0690 (14)0.0089 (9)0.0048 (9)0.0194 (10)
C16'0.0458 (11)0.0342 (10)0.0533 (12)0.0083 (8)0.0090 (9)0.0096 (8)
C170.0578 (16)0.0537 (15)0.164 (3)0.0169 (13)0.0138 (18)0.0396 (18)
C17'0.0481 (14)0.0622 (16)0.133 (3)0.0216 (12)0.0126 (15)0.0261 (17)
C180.085 (2)0.0621 (16)0.0777 (19)0.0252 (15)0.0165 (15)0.0008 (14)
C18'0.0492 (12)0.0575 (14)0.0698 (16)0.0152 (11)0.0025 (11)0.0143 (12)
N10.0304 (8)0.0511 (10)0.0536 (10)0.0118 (7)0.0061 (7)0.0111 (8)
N1'0.0508 (10)0.0352 (8)0.0536 (10)0.0139 (7)0.0004 (8)0.0170 (7)
O10.0344 (8)0.0593 (10)0.1242 (16)0.0154 (7)0.0048 (9)0.0333 (10)
O1'0.0514 (9)0.0411 (8)0.1038 (14)0.0149 (7)0.0113 (9)0.0193 (8)
O2'0.0505 (8)0.0299 (7)0.0568 (9)0.0071 (6)0.0044 (6)0.0141 (6)
O20.0271 (6)0.0479 (8)0.0540 (8)0.0069 (6)0.0029 (5)0.0133 (6)
O30.0295 (8)0.0578 (10)0.1401 (18)0.0059 (7)0.0090 (9)0.0355 (11)
O3'0.0524 (9)0.0339 (8)0.0981 (13)0.0090 (7)0.0087 (9)0.0167 (8)
Cl1'0.0443 (3)0.0753 (5)0.0916 (5)0.0002 (3)0.0115 (3)0.0129 (4)
Cl10.0716 (4)0.0471 (3)0.0927 (5)0.0067 (3)0.0227 (3)0.0194 (3)
Geometric parameters (Å, º) top
C1—C61.372 (3)C11—C121.409 (3)
C1—C21.385 (3)C11—C161.484 (3)
C1—Cl11.735 (2)C11'—C12'1.402 (3)
C1'—C6'1.377 (3)C11'—C16'1.483 (3)
C1'—C2'1.388 (4)C12—N11.339 (3)
C1'—Cl1'1.736 (2)C12—C131.492 (3)
C2—C31.370 (3)C12'—N1'1.339 (3)
C2—H20.9300C12'—C13'1.497 (3)
C2'—C3'1.379 (3)C13—C141.527 (3)
C2'—H2'0.9300C13—H13A0.9700
C3'—C4'1.389 (3)C13—H13B0.9700
C3'—H3'0.9300C13'—C14'1.532 (3)
C3—C41.390 (3)C13'—H13C0.9700
C3—H30.9300C13'—H13D0.9700
C4—O21.378 (2)C14—C171.527 (3)
C4—C51.390 (3)C14—C181.533 (4)
C4'—O2'1.374 (3)C14—C151.531 (3)
C4'—C5'1.388 (3)C14'—C18'1.529 (4)
C5—C61.395 (3)C14'—C17'1.533 (3)
C5—C71.470 (3)C14'—C15'1.533 (3)
C5'—C6'1.393 (3)C15'—C16'1.503 (3)
C5'—C7'1.471 (3)C15'—H15A0.9700
C6'—H6'0.9300C15'—H15B0.9700
C6—H60.9300C15—C161.499 (3)
C7'—O1'1.222 (2)C15—H15C0.9700
C7'—C8'1.468 (3)C15—H15D0.9700
C7—O11.216 (2)C16—O31.212 (3)
C7—C81.466 (3)C16'—O3'1.216 (2)
C8—C101.387 (3)C17—H17A0.9600
C8—C91.398 (3)C17—H17B0.9600
C8'—C10'1.384 (3)C17—H17C0.9600
C8'—C9'1.395 (3)C17'—H17D0.9600
C9—N11.322 (3)C17'—H17E0.9600
C9—O21.361 (2)C17'—H17F0.9600
C9'—N1'1.326 (3)C18—H18A0.9600
C9'—O2'1.362 (2)C18—H18B0.9600
C10—C111.371 (3)C18—H18C0.9600
C10—H100.9300C18'—H18D0.9600
C10'—C11'1.377 (3)C18'—H18E0.9600
C10'—H10'0.9300C18'—H18F0.9600
C6—C1—C2120.8 (2)C11'—C12'—C13'120.59 (18)
C6—C1—Cl1118.75 (18)C12—C13—C14113.78 (19)
C2—C1—Cl1120.41 (17)C12—C13—H13A108.8
C6'—C1'—C2'121.0 (2)C14—C13—H13A108.8
C6'—C1'—Cl1'119.3 (2)C12—C13—H13B108.8
C2'—C1'—Cl1'119.64 (17)C14—C13—H13B108.8
C3—C2—C1120.21 (19)H13A—C13—H13B107.7
C3—C2—H2119.9C12'—C13'—C14'113.01 (18)
C1—C2—H2119.9C12'—C13'—H13C109.0
C3'—C2'—C1'119.8 (2)C14'—C13'—H13C109.0
C3'—C2'—H2'120.1C12'—C13'—H13D109.0
C1'—C2'—H2'120.1C14'—C13'—H13D109.0
C2'—C3'—C4'119.2 (2)H13C—C13'—H13D107.8
C2'—C3'—H3'120.4C13—C14—C17110.4 (2)
C4'—C3'—H3'120.4C13—C14—C18109.7 (2)
C2—C3—C4119.4 (2)C17—C14—C18109.3 (2)
C2—C3—H3120.3C13—C14—C15108.6 (2)
C4—C3—H3120.3C17—C14—C15109.3 (2)
O2—C4—C3116.00 (18)C18—C14—C15109.5 (2)
O2—C4—C5123.13 (17)C18'—C14'—C17'109.1 (2)
C3—C4—C5120.9 (2)C18'—C14'—C13'110.3 (2)
O2'—C4'—C5'123.44 (17)C17'—C14'—C13'109.4 (2)
O2'—C4'—C3'115.37 (19)C18'—C14'—C15'109.7 (2)
C5'—C4'—C3'121.2 (2)C17'—C14'—C15'109.6 (2)
C4—C5—C6118.95 (18)C13'—C14'—C15'108.7 (2)
C4—C5—C7120.38 (19)C16'—C15'—C14'113.85 (18)
C6—C5—C7120.65 (18)C16'—C15'—H15A108.8
C4'—C5'—C6'119.05 (18)C14'—C15'—H15A108.8
C4'—C5'—C7'119.92 (19)C16'—C15'—H15B108.8
C6'—C5'—C7'121.02 (19)C14'—C15'—H15B108.8
C1'—C6'—C5'119.6 (2)H15A—C15'—H15B107.7
C1'—C6'—H6'120.2C16—C15—C14114.19 (19)
C5'—C6'—H6'120.2C16—C15—H15C108.7
C1—C6—C5119.7 (2)C14—C15—H15C108.7
C1—C6—H6120.1C16—C15—H15D108.7
C5—C6—H6120.1C14—C15—H15D108.7
O1'—C7'—C8'122.76 (18)H15C—C15—H15D107.6
O1'—C7'—C5'123.1 (2)O3—C16—C11120.3 (2)
C8'—C7'—C5'114.11 (17)O3—C16—C15122.1 (2)
O1—C7—C8122.87 (19)C11—C16—C15117.52 (18)
O1—C7—C5123.4 (2)O3'—C16'—C11'120.49 (19)
C8—C7—C5113.76 (17)O3'—C16'—C15'121.99 (19)
C10—C8—C9116.18 (18)C11'—C16'—C15'117.51 (18)
C10—C8—C7122.19 (17)C14—C17—H17A109.5
C9—C8—C7121.63 (17)C14—C17—H17B109.5
C10'—C8'—C9'116.13 (18)H17A—C17—H17B109.5
C10'—C8'—C7'122.48 (17)C14—C17—H17C109.5
C9'—C8'—C7'121.38 (17)H17A—C17—H17C109.5
N1—C9—O2112.46 (16)H17B—C17—H17C109.5
N1—C9—C8125.55 (17)C14'—C17'—H17D109.5
O2—C9—C8121.99 (18)C14'—C17'—H17E109.5
N1'—C9'—O2'112.55 (16)H17D—C17'—H17E109.5
N1'—C9'—C8'125.45 (17)C14'—C17'—H17F109.5
O2'—C9'—C8'121.99 (18)H17D—C17'—H17F109.5
C11—C10—C8119.92 (17)H17E—C17'—H17F109.5
C11—C10—H10120.0C14—C18—H18A109.5
C8—C10—H10120.0C14—C18—H18B109.5
C11'—C10'—C8'120.33 (17)H18A—C18—H18B109.5
C11'—C10'—H10'119.8C14—C18—H18C109.5
C8'—C10'—H10'119.8H18A—C18—H18C109.5
C10—C11—C12119.19 (18)H18B—C18—H18C109.5
C10—C11—C16120.10 (17)C14'—C18'—H18D109.5
C12—C11—C16120.71 (19)C14'—C18'—H18E109.5
C10'—C11'—C12'118.57 (18)H18D—C18'—H18E109.5
C10'—C11'—C16'120.37 (17)C14'—C18'—H18F109.5
C12'—C11'—C16'121.06 (18)H18D—C18'—H18F109.5
N1—C12—C11121.82 (19)H18E—C18'—H18F109.5
N1—C12—C13117.67 (18)C9—N1—C12117.33 (16)
C11—C12—C13120.49 (18)C9'—N1'—C12'117.15 (17)
N1'—C12'—C11'122.37 (19)C9'—O2'—C4'119.03 (15)
N1'—C12'—C13'117.04 (18)C9—O2—C4118.93 (15)
C6—C1—C2—C31.1 (3)C8—C10—C11—C16179.46 (19)
Cl1—C1—C2—C3179.03 (17)C8'—C10'—C11'—C12'0.3 (3)
C6'—C1'—C2'—C3'1.7 (3)C8'—C10'—C11'—C16'179.97 (18)
Cl1'—C1'—C2'—C3'178.16 (17)C10—C11—C12—N11.0 (3)
C1'—C2'—C3'—C4'0.1 (3)C16—C11—C12—N1179.6 (2)
C1—C2—C3—C40.4 (3)C10—C11—C12—C13177.3 (2)
C2—C3—C4—O2177.88 (18)C16—C11—C12—C132.0 (3)
C2—C3—C4—C51.4 (3)C10'—C11'—C12'—N1'0.1 (3)
C2'—C3'—C4'—O2'178.43 (18)C16'—C11'—C12'—N1'179.75 (19)
C2'—C3'—C4'—C5'1.7 (3)C10'—C11'—C12'—C13'179.5 (2)
O2—C4—C5—C6178.33 (17)C16'—C11'—C12'—C13'0.2 (3)
C3—C4—C5—C60.9 (3)N1—C12—C13—C14153.4 (2)
O2—C4—C5—C73.2 (3)C11—C12—C13—C1428.2 (3)
C3—C4—C5—C7177.54 (18)N1'—C12'—C13'—C14'151.8 (2)
O2'—C4'—C5'—C6'178.27 (18)C11'—C12'—C13'—C14'27.8 (3)
C3'—C4'—C5'—C6'1.9 (3)C12—C13—C14—C17172.4 (2)
O2'—C4'—C5'—C7'2.7 (3)C12—C13—C14—C1867.0 (3)
C3'—C4'—C5'—C7'177.18 (19)C12—C13—C14—C1552.6 (3)
C2'—C1'—C6'—C5'1.5 (3)C12'—C13'—C14'—C18'66.8 (3)
Cl1'—C1'—C6'—C5'178.33 (16)C12'—C13'—C14'—C17'173.1 (2)
C4'—C5'—C6'—C1'0.3 (3)C12'—C13'—C14'—C15'53.5 (3)
C7'—C5'—C6'—C1'178.77 (19)C18'—C14'—C15'—C16'66.6 (3)
C2—C1—C6—C51.6 (3)C17'—C14'—C15'—C16'173.6 (2)
Cl1—C1—C6—C5178.52 (16)C13'—C14'—C15'—C16'54.1 (3)
C4—C5—C6—C10.6 (3)C13—C14—C15—C1653.8 (3)
C7—C5—C6—C1179.05 (19)C17—C14—C15—C16174.3 (3)
C4'—C5'—C7'—O1'175.9 (2)C18—C14—C15—C1665.9 (3)
C6'—C5'—C7'—O1'3.1 (3)C10—C11—C16—O31.4 (4)
C4'—C5'—C7'—C8'3.9 (3)C12—C11—C16—O3179.3 (2)
C6'—C5'—C7'—C8'177.10 (18)C10—C11—C16—C15176.5 (2)
C4—C5—C7—O1175.2 (2)C12—C11—C16—C152.8 (3)
C6—C5—C7—O13.2 (3)C14—C15—C16—O3152.3 (3)
C4—C5—C7—C84.4 (3)C14—C15—C16—C1129.9 (3)
C6—C5—C7—C8177.16 (18)C10'—C11'—C16'—O3'1.5 (3)
O1—C7—C8—C102.6 (3)C12'—C11'—C16'—O3'178.8 (2)
C5—C7—C8—C10177.72 (18)C10'—C11'—C16'—C15'179.6 (2)
O1—C7—C8—C9177.4 (2)C12'—C11'—C16'—C15'0.1 (3)
C5—C7—C8—C92.2 (3)C14'—C15'—C16'—O3'152.9 (2)
O1'—C7'—C8'—C10'2.4 (3)C14'—C15'—C16'—C11'28.2 (3)
C5'—C7'—C8'—C10'177.78 (17)O2—C9—N1—C12179.43 (17)
O1'—C7'—C8'—C9'177.0 (2)C8—C9—N1—C121.1 (3)
C5'—C7'—C8'—C9'2.8 (3)C11—C12—N1—C90.5 (3)
C10—C8—C9—N11.9 (3)C13—C12—N1—C9177.90 (19)
C7—C8—C9—N1178.08 (19)O2'—C9'—N1'—C12'179.88 (17)
C10—C8—C9—O2178.65 (17)C8'—C9'—N1'—C12'0.4 (3)
C7—C8—C9—O21.4 (3)C11'—C12'—N1'—C9'0.3 (3)
C10'—C8'—C9'—N1'0.1 (3)C13'—C12'—N1'—C9'179.85 (19)
C7'—C8'—C9'—N1'179.33 (18)N1'—C9'—O2'—C4'179.10 (16)
C10'—C8'—C9'—O2'179.83 (17)C8'—C9'—O2'—C4'1.2 (3)
C7'—C8'—C9'—O2'0.4 (3)C5'—C4'—O2'—C9'0.0 (3)
C9—C8—C10—C111.2 (3)C3'—C4'—O2'—C9'179.84 (17)
C7—C8—C10—C11178.79 (19)N1—C9—O2—C4176.59 (16)
C9'—C8'—C10'—C11'0.3 (3)C8—C9—O2—C42.9 (3)
C7'—C8'—C10'—C11'179.69 (18)C3—C4—O2—C9178.66 (17)
C8—C10—C11—C120.2 (3)C5—C4—O2—C90.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O3i0.932.333.255 (3)174
C2—H2···O3i0.932.383.309 (3)173
Symmetry code: (i) x+1, y1, z.

Experimental details

Crystal data
Chemical formulaC18H14ClNO3
Mr327.75
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)11.4135 (4), 11.6663 (5), 13.5810 (6)
α, β, γ (°)69.265 (3), 73.868 (2), 64.998 (5)
V3)1515.11 (12)
Z4
Radiation typeMo Kα
µ (mm1)0.27
Crystal size (mm)0.30 × 0.25 × 0.20
Data collection
DiffractometerBruker SMART APEXII area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2008)
Tmin, Tmax0.924, 0.949
No. of measured, independent and
observed [I > 2σ(I)] reflections
26747, 7488, 5384
Rint0.033
(sin θ/λ)max1)0.669
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.167, 0.99
No. of reflections7488
No. of parameters419
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.27, 0.33

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O3i0.932.333.255 (3)174
C2'—H2'···O3'i0.932.383.309 (3)173
Symmetry code: (i) x+1, y1, z.
 

Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. TS also thanks the DST for an Inspire fellowship.

References

First citationBennett, I., Broom, N. J. P., Cassels, R., Elder, J. S., Masson, N. D. & O'Hanlon, P. J. (1999). Bioorg. Med. Chem. Lett. 9, 1847–1852.  Web of Science CrossRef PubMed CAS
First citationBruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals
First citationÖztürk Yildirim, S., Butcher, R. J., El-Khouly, A., Safak, C. & Şimsek, R. (2012). Acta Cryst. E68, o3365–o3366.  CSD CrossRef IUCr Journals
First citationSato, K., Yamazoe, S., Yamamoto, R., Ohata, S., Tarui, A., Omote, M., Kumadaki, I. & Ando, A. (2008). Org. Lett. 10, 2405–2408.  Web of Science CrossRef PubMed CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals

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