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

Srinivasan, T.; Yuvaraj, P.; Reddy, B.S.R.; Velmurugan, D.

doi:10.1107/S1600536813001062

organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o253

doi:10.1107/S1600536813001062

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

Thothadri Srinivasan,^a Panneerselvam Yuvaraj,^b Boreddy S. R. Reddy ^b and Devadasan Velmurugan ^a ^*

^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 –A–A–B–B–A–A– manner, with a number of π–π 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 ); Sato et al. (2008 ). For a related structure, see: Öztürk Yildirim et al. (2012 ).

Experimental

Crystal data

C₁₈H₁₄ClNO₃
M_r = 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 ) T_min = 0.924, T_max = 0.949
26747 measured reflections
7488 independent reflections
5384 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.167
S = 0.99
7488 reflections
419 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813001062/su2550sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813001062/su2550Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813001062/su2550Isup3.cml

checkCIF report

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.

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

	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.
	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

C₁₈H₁₄ClNO₃	Z = 4
M_r = 327.75	F(000) = 680
Triclinic, P1	D_x = 1.437 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.4135 (4) Å	Cell parameters from 7488 reflections
b = 11.6663 (5) Å	θ = 1.6–28.4°
c = 13.5810 (6) Å	µ = 0.27 mm⁻¹
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 tube	5384 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ω and ϕ scans	θ_max = 28.4°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −15→14
T_min = 0.924, T_max = 0.949	k = −15→15
26747 measured reflections	l = −18→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.167	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0783P)² + 0.7873P] where P = (F_o² + 2F_c²)/3
7488 reflections	(Δ/σ)_max < 0.001
419 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₈H₁₄ClNO₃	γ = 64.998 (5)°
M_r = 327.75	V = 1515.11 (12) Å³
Triclinic, P1	Z = 4
a = 11.4135 (4) Å	Mo Kα radiation
b = 11.6663 (5) Å	µ = 0.27 mm⁻¹
c = 13.5810 (6) Å	T = 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)
T_min = 0.924, T_max = 0.949	R_int = 0.033
26747 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.167	H-atom parameters constrained
S = 0.99	Δρ_max = 0.27 e Å⁻³
7488 reflections	Δρ_min = −0.33 e Å⁻³
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

	x	y	z	U_iso*/U_eq
C1	0.5452 (2)	0.2391 (2)	0.17141 (17)	0.0507 (5)
C1'	0.7356 (2)	0.4947 (2)	0.32726 (17)	0.0547 (5)
C2	0.6544 (2)	0.2742 (2)	0.14200 (17)	0.0528 (5)
H2	0.7376	0.2098	0.1389	0.063*
C2'	0.7043 (2)	0.3837 (2)	0.35361 (17)	0.0558 (6)
H2'	0.7703	0.3019	0.3552	0.067*
C3'	0.5750 (2)	0.3948 (2)	0.37743 (17)	0.0525 (5)
H3'	0.5532	0.3209	0.3951	0.063*
C3	0.64025 (19)	0.4033 (2)	0.11754 (17)	0.0492 (5)
H3	0.7135	0.4271	0.0973	0.059*
C4	0.51544 (18)	0.4985 (2)	0.12322 (14)	0.0411 (4)
C4'	0.4777 (2)	0.51767 (19)	0.37477 (15)	0.0432 (4)
C5	0.40526 (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'	0.6617	0.6895	0.3109	0.061*
C6	0.4216 (2)	0.3327 (2)	0.17485 (17)	0.0489 (5)
H6	0.3490	0.3083	0.1930	0.059*
C7'	0.4033 (2)	0.75624 (19)	0.35395 (16)	0.0448 (4)
C7	0.27378 (19)	0.5668 (2)	0.15261 (17)	0.0458 (5)
C8	0.27349 (17)	0.6992 (2)	0.13091 (15)	0.0401 (4)
C8'	0.27101 (19)	0.75360 (18)	0.37550 (14)	0.0386 (4)
C9	0.38973 (17)	0.7232 (2)	0.10728 (14)	0.0395 (4)
C9'	0.25063 (19)	0.63696 (18)	0.39621 (15)	0.0403 (4)
C10	0.15855 (18)	0.8078 (2)	0.13264 (16)	0.0431 (4)
H10	0.0782	0.7981	0.1466	0.052*
C10'	0.15975 (19)	0.86517 (18)	0.37749 (15)	0.0406 (4)
H10'	0.1675	0.9457	0.3645	0.049*
C11	0.16353 (18)	0.9292 (2)	0.11373 (16)	0.0433 (4)
C11'	0.0377 (2)	0.85759 (19)	0.39857 (16)	0.0419 (4)
C12	0.28618 (19)	0.9417 (2)	0.09298 (16)	0.0452 (4)
C12'	0.0290 (2)	0.73483 (19)	0.41838 (16)	0.0443 (4)
C13	0.2948 (2)	1.0714 (2)	0.0769 (2)	0.0595 (6)
H13A	0.3744	1.0758	0.0288	0.071*
H13B	0.3009	1.0774	0.1446	0.071*
C13'	−0.1015 (2)	0.7213 (2)	0.4426 (2)	0.0604 (6)
H13C	−0.0945	0.6345	0.4897	0.072*
H13D	−0.1256	0.7286	0.3770	0.072*
C14	0.1788 (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)
H15A	−0.2399	0.9786	0.3584	0.070*
H15B	−0.2753	1.0267	0.4606	0.070*
C15	0.0525 (2)	1.1739 (2)	0.1015 (2)	0.0668 (7)
H15C	0.0477	1.1832	0.1709	0.080*
H15D	−0.0214	1.2446	0.0697	0.080*
C16	0.0408 (2)	1.0454 (2)	0.1164 (2)	0.0532 (5)
C16'	−0.0816 (2)	0.97710 (19)	0.40067 (17)	0.0470 (5)
C17	0.1858 (3)	1.3168 (3)	0.0318 (3)	0.0908 (11)
H17A	0.2678	1.3235	−0.0077	0.136*
H17B	0.1789	1.3172	0.1038	0.136*
H17C	0.1153	1.3900	−0.0007	0.136*
C17'	−0.3419 (3)	0.8143 (3)	0.5042 (3)	0.0808 (9)
H17D	−0.4098	0.8793	0.5368	0.121*
H17E	−0.3400	0.7283	0.5472	0.121*
H17F	−0.3586	0.8286	0.4345	0.121*
C18	0.1796 (3)	1.1930 (3)	−0.0825 (2)	0.0802 (8)
H18A	0.2588	1.2024	−0.1261	0.120*
H18B	0.1058	1.2663	−0.1102	0.120*
H18C	0.1746	1.1130	−0.0826	0.120*
C18'	−0.1844 (2)	0.8035 (3)	0.6060 (2)	0.0637 (6)
H18D	−0.2542	0.8674	0.6386	0.096*
H18E	−0.1031	0.8129	0.6004	0.096*
H18F	−0.1803	0.7168	0.6487	0.096*
N1	0.39826 (15)	0.83855 (18)	0.08958 (14)	0.0470 (4)
N1'	0.13495 (18)	0.62525 (16)	0.41741 (14)	0.0474 (4)
O1	0.17423 (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)
O2	0.50909 (12)	0.62565 (14)	0.10098 (11)	0.0463 (3)
O3	−0.06431 (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)
Cl1	0.56258 (7)	0.07546 (6)	0.20440 (6)	0.0733 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0506 (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)
C2	0.0416 (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)
C3	0.0332 (9)	0.0575 (13)	0.0469 (11)	−0.0066 (9)	−0.0038 (8)	−0.0166 (9)
C4	0.0350 (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)
C5	0.0338 (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)
C6	0.0449 (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)
C7	0.0339 (9)	0.0511 (11)	0.0497 (11)	−0.0112 (8)	−0.0024 (8)	−0.0184 (9)
C8	0.0304 (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)
C9	0.0274 (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)
C10	0.0287 (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)
C11	0.0306 (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)
C12	0.0341 (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)
C13	0.0414 (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)
C14	0.0433 (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)
C15	0.0426 (12)	0.0531 (14)	0.100 (2)	−0.0092 (10)	0.0002 (12)	−0.0335 (13)
C16	0.0349 (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)
C17	0.0578 (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)
C18	0.085 (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)
N1	0.0304 (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)
O1	0.0344 (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)
O2	0.0271 (6)	0.0479 (8)	0.0540 (8)	−0.0069 (6)	−0.0029 (5)	−0.0133 (6)
O3	0.0295 (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)
Cl1	0.0716 (4)	0.0471 (3)	0.0927 (5)	−0.0067 (3)	−0.0227 (3)	−0.0194 (3)

Geometric parameters (Å, º) top

C1—C6	1.372 (3)	C11—C12	1.409 (3)
C1—C2	1.385 (3)	C11—C16	1.484 (3)
C1—Cl1	1.735 (2)	C11'—C12'	1.402 (3)
C1'—C6'	1.377 (3)	C11'—C16'	1.483 (3)
C1'—C2'	1.388 (4)	C12—N1	1.339 (3)
C1'—Cl1'	1.736 (2)	C12—C13	1.492 (3)
C2—C3	1.370 (3)	C12'—N1'	1.339 (3)
C2—H2	0.9300	C12'—C13'	1.497 (3)
C2'—C3'	1.379 (3)	C13—C14	1.527 (3)
C2'—H2'	0.9300	C13—H13A	0.9700
C3'—C4'	1.389 (3)	C13—H13B	0.9700
C3'—H3'	0.9300	C13'—C14'	1.532 (3)
C3—C4	1.390 (3)	C13'—H13C	0.9700
C3—H3	0.9300	C13'—H13D	0.9700
C4—O2	1.378 (2)	C14—C17	1.527 (3)
C4—C5	1.390 (3)	C14—C18	1.533 (4)
C4'—O2'	1.374 (3)	C14—C15	1.531 (3)
C4'—C5'	1.388 (3)	C14'—C18'	1.529 (4)
C5—C6	1.395 (3)	C14'—C17'	1.533 (3)
C5—C7	1.470 (3)	C14'—C15'	1.533 (3)
C5'—C6'	1.393 (3)	C15'—C16'	1.503 (3)
C5'—C7'	1.471 (3)	C15'—H15A	0.9700
C6'—H6'	0.9300	C15'—H15B	0.9700
C6—H6	0.9300	C15—C16	1.499 (3)
C7'—O1'	1.222 (2)	C15—H15C	0.9700
C7'—C8'	1.468 (3)	C15—H15D	0.9700
C7—O1	1.216 (2)	C16—O3	1.212 (3)
C7—C8	1.466 (3)	C16'—O3'	1.216 (2)
C8—C10	1.387 (3)	C17—H17A	0.9600
C8—C9	1.398 (3)	C17—H17B	0.9600
C8'—C10'	1.384 (3)	C17—H17C	0.9600
C8'—C9'	1.395 (3)	C17'—H17D	0.9600
C9—N1	1.322 (3)	C17'—H17E	0.9600
C9—O2	1.361 (2)	C17'—H17F	0.9600
C9'—N1'	1.326 (3)	C18—H18A	0.9600
C9'—O2'	1.362 (2)	C18—H18B	0.9600
C10—C11	1.371 (3)	C18—H18C	0.9600
C10—H10	0.9300	C18'—H18D	0.9600
C10'—C11'	1.377 (3)	C18'—H18E	0.9600
C10'—H10'	0.9300	C18'—H18F	0.9600

C6—C1—C2	120.8 (2)	C11'—C12'—C13'	120.59 (18)
C6—C1—Cl1	118.75 (18)	C12—C13—C14	113.78 (19)
C2—C1—Cl1	120.41 (17)	C12—C13—H13A	108.8
C6'—C1'—C2'	121.0 (2)	C14—C13—H13A	108.8
C6'—C1'—Cl1'	119.3 (2)	C12—C13—H13B	108.8
C2'—C1'—Cl1'	119.64 (17)	C14—C13—H13B	108.8
C3—C2—C1	120.21 (19)	H13A—C13—H13B	107.7
C3—C2—H2	119.9	C12'—C13'—C14'	113.01 (18)
C1—C2—H2	119.9	C12'—C13'—H13C	109.0
C3'—C2'—C1'	119.8 (2)	C14'—C13'—H13C	109.0
C3'—C2'—H2'	120.1	C12'—C13'—H13D	109.0
C1'—C2'—H2'	120.1	C14'—C13'—H13D	109.0
C2'—C3'—C4'	119.2 (2)	H13C—C13'—H13D	107.8
C2'—C3'—H3'	120.4	C13—C14—C17	110.4 (2)
C4'—C3'—H3'	120.4	C13—C14—C18	109.7 (2)
C2—C3—C4	119.4 (2)	C17—C14—C18	109.3 (2)
C2—C3—H3	120.3	C13—C14—C15	108.6 (2)
C4—C3—H3	120.3	C17—C14—C15	109.3 (2)
O2—C4—C3	116.00 (18)	C18—C14—C15	109.5 (2)
O2—C4—C5	123.13 (17)	C18'—C14'—C17'	109.1 (2)
C3—C4—C5	120.9 (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—C6	118.95 (18)	C13'—C14'—C15'	108.7 (2)
C4—C5—C7	120.38 (19)	C16'—C15'—C14'	113.85 (18)
C6—C5—C7	120.65 (18)	C16'—C15'—H15A	108.8
C4'—C5'—C6'	119.05 (18)	C14'—C15'—H15A	108.8
C4'—C5'—C7'	119.92 (19)	C16'—C15'—H15B	108.8
C6'—C5'—C7'	121.02 (19)	C14'—C15'—H15B	108.8
C1'—C6'—C5'	119.6 (2)	H15A—C15'—H15B	107.7
C1'—C6'—H6'	120.2	C16—C15—C14	114.19 (19)
C5'—C6'—H6'	120.2	C16—C15—H15C	108.7
C1—C6—C5	119.7 (2)	C14—C15—H15C	108.7
C1—C6—H6	120.1	C16—C15—H15D	108.7
C5—C6—H6	120.1	C14—C15—H15D	108.7
O1'—C7'—C8'	122.76 (18)	H15C—C15—H15D	107.6
O1'—C7'—C5'	123.1 (2)	O3—C16—C11	120.3 (2)
C8'—C7'—C5'	114.11 (17)	O3—C16—C15	122.1 (2)
O1—C7—C8	122.87 (19)	C11—C16—C15	117.52 (18)
O1—C7—C5	123.4 (2)	O3'—C16'—C11'	120.49 (19)
C8—C7—C5	113.76 (17)	O3'—C16'—C15'	121.99 (19)
C10—C8—C9	116.18 (18)	C11'—C16'—C15'	117.51 (18)
C10—C8—C7	122.19 (17)	C14—C17—H17A	109.5
C9—C8—C7	121.63 (17)	C14—C17—H17B	109.5
C10'—C8'—C9'	116.13 (18)	H17A—C17—H17B	109.5
C10'—C8'—C7'	122.48 (17)	C14—C17—H17C	109.5
C9'—C8'—C7'	121.38 (17)	H17A—C17—H17C	109.5
N1—C9—O2	112.46 (16)	H17B—C17—H17C	109.5
N1—C9—C8	125.55 (17)	C14'—C17'—H17D	109.5
O2—C9—C8	121.99 (18)	C14'—C17'—H17E	109.5
N1'—C9'—O2'	112.55 (16)	H17D—C17'—H17E	109.5
N1'—C9'—C8'	125.45 (17)	C14'—C17'—H17F	109.5
O2'—C9'—C8'	121.99 (18)	H17D—C17'—H17F	109.5
C11—C10—C8	119.92 (17)	H17E—C17'—H17F	109.5
C11—C10—H10	120.0	C14—C18—H18A	109.5
C8—C10—H10	120.0	C14—C18—H18B	109.5
C11'—C10'—C8'	120.33 (17)	H18A—C18—H18B	109.5
C11'—C10'—H10'	119.8	C14—C18—H18C	109.5
C8'—C10'—H10'	119.8	H18A—C18—H18C	109.5
C10—C11—C12	119.19 (18)	H18B—C18—H18C	109.5
C10—C11—C16	120.10 (17)	C14'—C18'—H18D	109.5
C12—C11—C16	120.71 (19)	C14'—C18'—H18E	109.5
C10'—C11'—C12'	118.57 (18)	H18D—C18'—H18E	109.5
C10'—C11'—C16'	120.37 (17)	C14'—C18'—H18F	109.5
C12'—C11'—C16'	121.06 (18)	H18D—C18'—H18F	109.5
N1—C12—C11	121.82 (19)	H18E—C18'—H18F	109.5
N1—C12—C13	117.67 (18)	C9—N1—C12	117.33 (16)
C11—C12—C13	120.49 (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—C4	118.93 (15)

C6—C1—C2—C3	1.1 (3)	C8—C10—C11—C16	−179.46 (19)
Cl1—C1—C2—C3	−179.03 (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—N1	1.0 (3)
C1'—C2'—C3'—C4'	−0.1 (3)	C16—C11—C12—N1	−179.6 (2)
C1—C2—C3—C4	0.4 (3)	C10—C11—C12—C13	−177.3 (2)
C2—C3—C4—O2	177.88 (18)	C16—C11—C12—C13	2.0 (3)
C2—C3—C4—C5	−1.4 (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—C6	−178.33 (17)	C16'—C11'—C12'—C13'	−0.2 (3)
C3—C4—C5—C6	0.9 (3)	N1—C12—C13—C14	153.4 (2)
O2—C4—C5—C7	3.2 (3)	C11—C12—C13—C14	−28.2 (3)
C3—C4—C5—C7	−177.54 (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—C17	172.4 (2)
O2'—C4'—C5'—C7'	2.7 (3)	C12—C13—C14—C18	−67.0 (3)
C3'—C4'—C5'—C7'	−177.18 (19)	C12—C13—C14—C15	52.6 (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—C5	−1.6 (3)	C17'—C14'—C15'—C16'	−173.6 (2)
Cl1—C1—C6—C5	178.52 (16)	C13'—C14'—C15'—C16'	−54.1 (3)
C4—C5—C6—C1	0.6 (3)	C13—C14—C15—C16	−53.8 (3)
C7—C5—C6—C1	179.05 (19)	C17—C14—C15—C16	−174.3 (3)
C4'—C5'—C7'—O1'	175.9 (2)	C18—C14—C15—C16	65.9 (3)
C6'—C5'—C7'—O1'	−3.1 (3)	C10—C11—C16—O3	−1.4 (4)
C4'—C5'—C7'—C8'	−3.9 (3)	C12—C11—C16—O3	179.3 (2)
C6'—C5'—C7'—C8'	177.10 (18)	C10—C11—C16—C15	176.5 (2)
C4—C5—C7—O1	175.2 (2)	C12—C11—C16—C15	−2.8 (3)
C6—C5—C7—O1	−3.2 (3)	C14—C15—C16—O3	−152.3 (3)
C4—C5—C7—C8	−4.4 (3)	C14—C15—C16—C11	29.9 (3)
C6—C5—C7—C8	177.16 (18)	C10'—C11'—C16'—O3'	1.5 (3)
O1—C7—C8—C10	2.6 (3)	C12'—C11'—C16'—O3'	−178.8 (2)
C5—C7—C8—C10	−177.72 (18)	C10'—C11'—C16'—C15'	−179.6 (2)
O1—C7—C8—C9	−177.4 (2)	C12'—C11'—C16'—C15'	0.1 (3)
C5—C7—C8—C9	2.2 (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—C12	179.43 (17)
O1'—C7'—C8'—C9'	−177.0 (2)	C8—C9—N1—C12	−1.1 (3)
C5'—C7'—C8'—C9'	2.8 (3)	C11—C12—N1—C9	−0.5 (3)
C10—C8—C9—N1	1.9 (3)	C13—C12—N1—C9	177.90 (19)
C7—C8—C9—N1	−178.08 (19)	O2'—C9'—N1'—C12'	−179.88 (17)
C10—C8—C9—O2	−178.65 (17)	C8'—C9'—N1'—C12'	0.4 (3)
C7—C8—C9—O2	1.4 (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—C11	−1.2 (3)	C3'—C4'—O2'—C9'	179.84 (17)
C7—C8—C10—C11	178.79 (19)	N1—C9—O2—C4	176.59 (16)
C9'—C8'—C10'—C11'	−0.3 (3)	C8—C9—O2—C4	−2.9 (3)
C7'—C8'—C10'—C11'	−179.69 (18)	C3—C4—O2—C9	−178.66 (17)
C8—C10—C11—C12	−0.2 (3)	C5—C4—O2—C9	0.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₄ClNO₃
M_r	327.75
Crystal system, space group	Triclinic, 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)
V (Å³)	1515.11 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.924, 0.949
No. of measured, independent and observed [I > 2σ(I)] reflections	26747, 7488, 5384
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.167, 0.99
No. of reflections	7488
No. of parameters	419
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	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.

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

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. Web of Science CrossRef PubMed CAS Google Scholar
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