3-(3-Chloro­benz­yl)-1H-isochromen-1-one

Abid, O.-U.-R.; Qadeer, G.; Rama, N.H.; Ruzicka, A.; Padelkova, Z.

doi:10.1107/S1600536808030274

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o2018

doi:10.1107/S1600536808030274

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3-(3-Chlorobenzyl)-1H-isochromen-1-one

Obaid-Ur-Rehman Abid,^a Ghulam Qadeer,^a Nasim Hasan Rama,^a ^* Ales Ruzicka ^b and Zdenka Padelkova ^b

^aDepartment of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan, and ^bDepartment of General and Inorganic Chemistry, Faculty of Chemical Technology, University of Pardubice, Nam. Cs. Legii' 565, 53210 Pardubice, Czech Republic
^*Correspondence e-mail: nasimhrama@yahoo.com

(Received 11 September 2008; accepted 20 September 2008; online 27 September 2008)

The asymmetric unit of the title compound, C₁₆H₁₁ClO₂, a chemically synthesized isocoumarin, contains three independent molecules. The benzopyran and benzene rings are approximately perpendicular to each other, forming dihedral angles ranging from 83.08 (14) to 87.43 (11)°. In the crystal structure, molecules are linked by intermolecular C—H⋯O hydrogen-bonding interactions, forming chains running parallel to the a axis.

Related literature

For the properties and applications of isocumarins, see: Barry (1964 ); Powers et al. (2002 ); Sturtz et al. (2002 ). For the crystal structure of a related compound, see: Abid et al. (2006 ). For related literature, see: Allen et al. (1987 ); Rossi et al. (2003 ); Thomas & Jens (1999 ).

Experimental

Crystal data

C₁₆H₁₁ClO₂
M_r = 270.70
Triclinic, $[P \overline 1]$
a = 8.1411 (8) Å
b = 15.0269 (14) Å
c = 16.4080 (16) Å
α = 91.696 (8)°
β = 98.478 (8)°
γ = 102.624 (6)°
V = 1933.4 (3) Å³
Z = 6
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 150 (1) K
0.36 × 0.28 × 0.13 mm

Data collection

Bruker–Nonius KappaCCD area-detector diffractometer
Absorption correction: Gaussian (Coppens et al., 1970 ) T_min = 0.930, T_max = 0.978
33806 measured reflections
8770 independent reflections
5387 reflections with I > 2σ(I)
R_int = 0.096

Refinement

R[F² > 2σ(F²)] = 0.093
wR(F²) = 0.280
S = 1.15
8770 reflections
514 parameters
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C216—H216⋯O11	0.93	2.56	3.437 (6)	158
C116—H116⋯O21	0.93	2.58	3.396 (6)	147
C26—H26⋯O22ⁱ	0.93	2.45	3.339 (7)	161
C36—H36⋯O32ⁱ	0.93	2.52	3.409 (6)	160
Symmetry code: (i) x+1, y, z.

Data collection: COLLECT (Hooft, 1998 ) and DENZO (Otwinowski & Minor, 1997 ); cell refinement: COLLECT and DENZO; data reduction: COLLECT and DENZO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808030274/rz2245sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808030274/rz2245Isup2.hkl

checkCIF report

Comment top

The isocoumarin nucleus is an abundant structural motif in natural products (Barry, 1964). Many constituents of the steadily growing class of known isocoumarins exhibit valuable biological properties such as antifungal (Sturtz et al., 2002), antitumor or cytotoxic, anti-inflammatory, anti-allergic (Rossi et al., 2003) and enzyme inhibitory activity (Powers et al.,2002). Naturally occurring halo-isocoumarins and their halogeno-3,4-dihydroiscoumarin derivatives are very rare. However, a few examples of naturally occurring chlorine containing isocoumarins are known (Thomas & Jens, 1999). In view of the importance of this class of compounds, the title compound, an isocoumarine derivative containing a 3-chlorobenzyl substituent, has been synthesized and its crystal structure is reported here.

The asymmetric unit of the title compound contains three crystallographically independent molecules of similar geometry (Fig.1). The molecules are not planar, the dihedral angles formed by the benzopyran ring with the corresponding benzene ring being 83.08 (14), 87.43 (11) and 84.25 (14)° for the molecules containing Cl11, Cl21 and Cl31, respectively. The bond lengths (Allen et al., 1987) and angles are within normal ranges and comparable with those reported for 3-(2-chlorobenzyl)isocoumarin (Abid et al., 2006). In the crystal packing, molecules are linked by intermolecular C—H···O hydrogen bonds (Table 1) into chains running parallel to the a axis (Fig. 2).

Related literature top

For the properties and applications of isocumarins, see: Barry (1964); Powers et al. (2002); Sturtz et al. (2002). For the crystal structure of a related compound, see: Abid et al. (2006).

For related literature, see: Allen et al. (1987); Rossi et al. (2003); Thomas & Jens (1999).

Experimental top

A mixture of 2-(3-chlorophenyl)acetic acid (4.76 g, 28 mmol) and thionyl chloride (2.94 ml, 34 mmol) was heated for 30 min in the presence of a few drops of DMF under reflux at 343 K to give 2-(3-chlorophenyl)acetyl chloride. Completion of the reaction was indicated by the disappearance of gas evolution. The removal of excess thionyl chloride was carried out under reduced pressure to afford 2-(3-chlorophenyl)acetyl chloride. Homophthalic acid (1.3 g, 7.2 mmol) was then added and the solution was refluxed for 6 hrs at 473 K with stirring. The reaction mixture was extracted with ethyl acetate (3 times 100 ml), and an aqueous solution of sodium carbonate (5%, 200 ml) was added to remove the unreacted homophthalic acid. The organic layer was separated, concentrated and chromatographed on silica gel using petroleum ether (313–353 K fractions) as eluent to afford the title compound (yield 62%; m.p. 350–351 K). Colourless single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethyl acetate solution.

Computing details top

Data collection: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997); cell refinement: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997); data reduction: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound, with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Crystal packing of the title compound viewed approximately along the a axis. Intermolecular C—H···O hydrogen bonds are shown as dashed lines.
	Fig. 3. The formation of the title compound.

3-(3-Chlorobenzyl)-1H-isochromen-1-one top

Crystal data top

C₁₆H₁₁ClO₂	Z = 6
M_r = 270.70	F(000) = 840
Triclinic, P1	D_x = 1.395 Mg m⁻³
Hall symbol: -P 1	Melting point: 350(1) K
a = 8.1411 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 15.0269 (14) Å	Cell parameters from 33934 reflections
c = 16.4080 (16) Å	θ = 1–27.5°
α = 91.696 (8)°	µ = 0.29 mm⁻¹
β = 98.478 (8)°	T = 150 K
γ = 102.624 (6)°	Block, colourless
V = 1933.4 (3) Å³	0.36 × 0.28 × 0.13 mm

Data collection top

Bruker–Nonius KappaCCD area-detector diffractometer	8770 independent reflections
Radiation source: fine-focus sealed tube	5387 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.096
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 1.8°
ϕ and ω scans to fill the Ewald sphere	h = −10→10
Absorption correction: integration (Gaussian; Coppens et al., 1970)	k = −19→19
T_min = 0.930, T_max = 0.978	l = −21→21
33806 measured reflections

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)] = 0.093	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.280	H-atom parameters constrained
S = 1.15	w = 1/[σ²(F_o²) + (0.0832P)² + 3.9759P] where P = (F_o² + 2F_c²)/3
8770 reflections	(Δ/σ)_max < 0.001
514 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₁₆H₁₁ClO₂	γ = 102.624 (6)°
M_r = 270.70	V = 1933.4 (3) Å³
Triclinic, P1	Z = 6
a = 8.1411 (8) Å	Mo Kα radiation
b = 15.0269 (14) Å	µ = 0.29 mm⁻¹
c = 16.4080 (16) Å	T = 150 K
α = 91.696 (8)°	0.36 × 0.28 × 0.13 mm
β = 98.478 (8)°

Data collection top

Bruker–Nonius KappaCCD area-detector diffractometer	8770 independent reflections
Absorption correction: integration (Gaussian; Coppens et al., 1970)	5387 reflections with I > 2σ(I)
T_min = 0.930, T_max = 0.978	R_int = 0.096
33806 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.093	0 restraints
wR(F²) = 0.280	H-atom parameters constrained
S = 1.15	Δρ_max = 0.51 e Å⁻³
8770 reflections	Δρ_min = −0.38 e Å⁻³
514 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

	x	y	z	U_iso*/U_eq
Cl11	−0.0861 (2)	0.69111 (11)	0.78787 (9)	0.0721 (4)
Cl31	−0.1878 (2)	0.34414 (12)	0.45567 (9)	0.0764 (5)
Cl21	−0.2374 (3)	0.96729 (13)	−0.13645 (9)	0.0865 (6)
O12	−0.3053 (4)	0.8902 (2)	0.4163 (2)	0.0466 (8)
C34	−0.0819 (5)	0.5570 (3)	0.1009 (2)	0.0369 (9)
O32	−0.4217 (4)	0.5627 (2)	0.09538 (19)	0.0452 (7)
O22	−0.3792 (4)	0.7443 (2)	0.2320 (2)	0.0506 (8)
C14	0.0400 (6)	0.8964 (3)	0.4355 (2)	0.0383 (9)
C23	−0.1317 (6)	0.8252 (3)	0.1859 (3)	0.0401 (10)
H23	−0.0798	0.8699	0.1540	0.048*
C19	−0.0270 (6)	0.9565 (3)	0.3839 (3)	0.0386 (9)
C11	−0.2077 (6)	0.9547 (3)	0.3750 (3)	0.0438 (10)
O31	−0.4003 (4)	0.6731 (2)	0.0103 (2)	0.0534 (8)
O11	−0.2803 (5)	1.0049 (3)	0.3363 (2)	0.0646 (10)
C31	−0.3272 (6)	0.6231 (3)	0.0492 (3)	0.0394 (9)
C29	−0.1117 (6)	0.7056 (3)	0.2811 (2)	0.0413 (10)
C35	0.0900 (6)	0.5559 (3)	0.1035 (3)	0.0456 (11)
H35	0.1377	0.5156	0.1362	0.055*
C24	−0.0311 (6)	0.7732 (3)	0.2336 (3)	0.0391 (9)
O21	−0.3788 (5)	0.6358 (3)	0.3182 (2)	0.0649 (10)
C110	−0.3759 (6)	0.7710 (3)	0.5034 (3)	0.0513 (12)
H110A	−0.4632	0.7392	0.4590	0.062*
H110B	−0.4276	0.8088	0.5360	0.062*
C32	−0.3542 (5)	0.5006 (3)	0.1420 (2)	0.0370 (9)
C311	−0.4318 (5)	0.3711 (3)	0.2324 (3)	0.0416 (10)
C13	−0.0723 (6)	0.8334 (3)	0.4773 (3)	0.0414 (10)
H13	−0.0287	0.7937	0.5124	0.050*
C22	−0.2965 (6)	0.8114 (3)	0.1858 (3)	0.0417 (10)
C21	−0.2929 (6)	0.6906 (3)	0.2800 (3)	0.0471 (11)
C113	−0.1807 (6)	0.6609 (3)	0.6859 (3)	0.0458 (11)
C112	−0.2401 (6)	0.7239 (3)	0.6380 (3)	0.0476 (11)
H112	−0.2317	0.7824	0.6608	0.057*
C212	−0.3309 (6)	0.9170 (3)	0.0091 (3)	0.0516 (12)
H212	−0.3752	0.8590	−0.0166	0.062*
C12	−0.2366 (6)	0.8308 (3)	0.4666 (3)	0.0400 (10)
C39	−0.1497 (5)	0.6193 (3)	0.0524 (2)	0.0349 (9)
C18	0.0777 (7)	1.0171 (3)	0.3405 (3)	0.0488 (11)
H18	0.0315	1.0559	0.3054	0.059*
C310	−0.4898 (6)	0.4452 (3)	0.1844 (3)	0.0458 (11)
H310A	−0.5882	0.4181	0.1435	0.055*
H310B	−0.5251	0.4859	0.2219	0.055*
C33	−0.1936 (6)	0.4969 (3)	0.1461 (3)	0.0402 (10)
H33	−0.1513	0.4549	0.1787	0.048*
C211	−0.3426 (6)	0.9338 (3)	0.0915 (3)	0.0472 (11)
C17	0.2471 (7)	1.0200 (3)	0.3494 (3)	0.0548 (13)
H17	0.3164	1.0606	0.3203	0.066*
C38	−0.0470 (6)	0.6788 (3)	0.0070 (3)	0.0443 (10)
H38	−0.0921	0.7204	−0.0250	0.053*
C312	−0.3485 (6)	0.3892 (3)	0.3126 (3)	0.0443 (10)
H312	−0.3297	0.4475	0.3380	0.053*
C313	−0.2922 (6)	0.3210 (4)	0.3550 (3)	0.0505 (12)
C111	−0.3126 (6)	0.7018 (3)	0.5568 (3)	0.0456 (11)
C26	0.2337 (7)	0.7326 (4)	0.2817 (3)	0.0620 (14)
H26	0.3502	0.7408	0.2815	0.074*
C15	0.2150 (6)	0.9013 (4)	0.4447 (3)	0.0514 (12)
H15	0.2634	0.8635	0.4800	0.062*
C210	−0.4238 (6)	0.8580 (4)	0.1400 (3)	0.0551 (13)
H210A	−0.4842	0.8822	0.1790	0.066*
H210B	−0.5065	0.8132	0.1025	0.066*
C214	−0.1859 (7)	1.0727 (3)	0.0021 (4)	0.0608 (14)
H214	−0.1334	1.1192	−0.0279	0.073*
C316	−0.4589 (7)	0.2834 (4)	0.1968 (3)	0.0588 (13)
H316	−0.5154	0.2699	0.1429	0.071*
C36	0.1877 (6)	0.6143 (3)	0.0579 (3)	0.0533 (12)
H36	0.3019	0.6129	0.0597	0.064*
C114	−0.1934 (9)	0.5750 (4)	0.6558 (4)	0.0702 (17)
H114	−0.1541	0.5325	0.6889	0.084*
C25	0.1436 (6)	0.7850 (4)	0.2350 (3)	0.0537 (12)
H25	0.1998	0.8289	0.2038	0.064*
C213	−0.2522 (7)	0.9871 (3)	−0.0338 (3)	0.0531 (12)
C27	0.1542 (8)	0.6675 (4)	0.3290 (3)	0.0605 (14)
H27	0.2174	0.6330	0.3612	0.073*
C37	0.1202 (6)	0.6752 (3)	0.0099 (3)	0.0521 (12)
H37	0.1887	0.7140	−0.0210	0.062*
C315	−0.4023 (8)	0.2162 (3)	0.2408 (4)	0.0642 (15)
H315	−0.4212	0.1575	0.2162	0.077*
C216	−0.2756 (7)	1.0201 (4)	0.1280 (3)	0.0584 (13)
H216	−0.2832	1.0321	0.1831	0.070*
C314	−0.3189 (7)	0.2345 (3)	0.3200 (4)	0.0571 (13)
H314	−0.2811	0.1891	0.3497	0.068*
C16	0.3164 (7)	0.9627 (4)	0.4017 (3)	0.0583 (13)
H16	0.4327	0.9652	0.4078	0.070*
C28	−0.0167 (7)	0.6535 (3)	0.3290 (3)	0.0540 (13)
H28	−0.0702	0.6095	0.3610	0.065*
C215	−0.1957 (9)	1.0890 (4)	0.0837 (4)	0.0730 (17)
H215	−0.1498	1.1469	0.1093	0.088*
C115	−0.2687 (11)	0.5514 (4)	0.5746 (4)	0.089 (2)
H115	−0.2785	0.4924	0.5527	0.107*
C116	−0.3259 (9)	0.6148 (4)	0.5254 (3)	0.0667 (16)
H116	−0.3745	0.5980	0.4707	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl11	0.0741 (10)	0.0797 (10)	0.0526 (8)	0.0050 (8)	−0.0034 (7)	0.0057 (7)
Cl31	0.0903 (11)	0.0920 (11)	0.0506 (8)	0.0367 (9)	−0.0020 (7)	0.0105 (7)
Cl21	0.1028 (13)	0.0933 (12)	0.0544 (8)	−0.0025 (10)	0.0208 (8)	0.0008 (8)
O12	0.0378 (17)	0.0530 (19)	0.0531 (18)	0.0140 (14)	0.0116 (14)	0.0182 (15)
C34	0.032 (2)	0.043 (2)	0.036 (2)	0.0082 (17)	0.0075 (17)	0.0017 (17)
O32	0.0337 (16)	0.0549 (19)	0.0517 (18)	0.0161 (14)	0.0098 (14)	0.0185 (15)
O22	0.0402 (18)	0.057 (2)	0.057 (2)	0.0092 (15)	0.0171 (15)	0.0186 (16)
C14	0.041 (2)	0.042 (2)	0.035 (2)	0.0130 (18)	0.0101 (18)	0.0014 (18)
C23	0.041 (2)	0.041 (2)	0.041 (2)	0.0087 (18)	0.0126 (19)	0.0096 (18)
C19	0.043 (2)	0.038 (2)	0.037 (2)	0.0101 (18)	0.0108 (18)	0.0015 (17)
C11	0.049 (3)	0.045 (3)	0.041 (2)	0.016 (2)	0.009 (2)	0.0130 (19)
O31	0.0475 (19)	0.057 (2)	0.061 (2)	0.0210 (16)	0.0082 (16)	0.0224 (16)
O11	0.061 (2)	0.073 (2)	0.072 (2)	0.029 (2)	0.0198 (19)	0.036 (2)
C31	0.044 (2)	0.039 (2)	0.038 (2)	0.0132 (19)	0.0074 (18)	0.0084 (18)
C29	0.053 (3)	0.039 (2)	0.031 (2)	0.0072 (19)	0.0074 (19)	0.0004 (17)
C35	0.035 (2)	0.047 (3)	0.058 (3)	0.0152 (19)	0.009 (2)	0.011 (2)
C24	0.042 (2)	0.036 (2)	0.040 (2)	0.0106 (18)	0.0081 (18)	0.0016 (18)
O21	0.067 (2)	0.063 (2)	0.063 (2)	−0.0004 (19)	0.0221 (19)	0.0241 (18)
C110	0.042 (3)	0.057 (3)	0.056 (3)	0.008 (2)	0.013 (2)	0.019 (2)
C32	0.036 (2)	0.041 (2)	0.033 (2)	0.0084 (18)	0.0047 (17)	0.0063 (17)
C311	0.032 (2)	0.045 (2)	0.047 (2)	0.0045 (18)	0.0101 (18)	0.011 (2)
C13	0.047 (3)	0.042 (2)	0.041 (2)	0.018 (2)	0.0117 (19)	0.0103 (19)
C22	0.048 (3)	0.039 (2)	0.038 (2)	0.0057 (19)	0.0154 (19)	0.0094 (18)
C21	0.056 (3)	0.041 (2)	0.043 (2)	0.003 (2)	0.012 (2)	0.006 (2)
C113	0.047 (3)	0.048 (3)	0.041 (2)	0.004 (2)	0.012 (2)	0.011 (2)
C112	0.049 (3)	0.037 (2)	0.055 (3)	0.002 (2)	0.011 (2)	0.004 (2)
C212	0.045 (3)	0.047 (3)	0.058 (3)	0.003 (2)	0.002 (2)	0.005 (2)
C12	0.040 (2)	0.039 (2)	0.043 (2)	0.0098 (18)	0.0086 (18)	0.0100 (18)
C39	0.033 (2)	0.036 (2)	0.034 (2)	0.0064 (16)	0.0062 (16)	0.0011 (16)
C18	0.055 (3)	0.042 (2)	0.050 (3)	0.007 (2)	0.015 (2)	0.008 (2)
C310	0.038 (2)	0.053 (3)	0.048 (3)	0.010 (2)	0.011 (2)	0.012 (2)
C33	0.044 (2)	0.040 (2)	0.040 (2)	0.0149 (19)	0.0073 (19)	0.0097 (18)
C211	0.040 (3)	0.046 (3)	0.057 (3)	0.012 (2)	0.006 (2)	0.015 (2)
C17	0.060 (3)	0.049 (3)	0.055 (3)	0.001 (2)	0.027 (2)	0.003 (2)
C38	0.047 (3)	0.043 (2)	0.044 (2)	0.009 (2)	0.011 (2)	0.0070 (19)
C312	0.044 (3)	0.043 (2)	0.048 (2)	0.0092 (19)	0.011 (2)	0.008 (2)
C313	0.050 (3)	0.060 (3)	0.045 (3)	0.014 (2)	0.016 (2)	0.012 (2)
C111	0.043 (3)	0.044 (2)	0.049 (3)	0.0022 (19)	0.014 (2)	0.011 (2)
C26	0.051 (3)	0.075 (4)	0.068 (3)	0.027 (3)	0.013 (3)	0.015 (3)
C15	0.041 (3)	0.060 (3)	0.056 (3)	0.015 (2)	0.011 (2)	0.007 (2)
C210	0.042 (3)	0.064 (3)	0.063 (3)	0.015 (2)	0.014 (2)	0.018 (3)
C214	0.065 (3)	0.044 (3)	0.068 (3)	−0.001 (2)	0.009 (3)	0.011 (2)
C316	0.061 (3)	0.058 (3)	0.054 (3)	0.009 (3)	0.005 (2)	−0.002 (2)
C36	0.036 (2)	0.055 (3)	0.071 (3)	0.009 (2)	0.014 (2)	0.007 (2)
C114	0.103 (5)	0.044 (3)	0.066 (4)	0.020 (3)	0.011 (3)	0.014 (3)
C25	0.047 (3)	0.064 (3)	0.056 (3)	0.018 (2)	0.018 (2)	0.014 (2)
C213	0.052 (3)	0.055 (3)	0.050 (3)	0.007 (2)	0.007 (2)	0.011 (2)
C27	0.069 (4)	0.063 (3)	0.052 (3)	0.027 (3)	−0.001 (3)	0.009 (2)
C37	0.047 (3)	0.049 (3)	0.061 (3)	0.006 (2)	0.019 (2)	0.012 (2)
C315	0.076 (4)	0.038 (3)	0.080 (4)	0.013 (3)	0.019 (3)	0.002 (3)
C216	0.071 (4)	0.055 (3)	0.052 (3)	0.022 (3)	0.006 (3)	0.004 (2)
C314	0.063 (3)	0.042 (3)	0.072 (4)	0.017 (2)	0.020 (3)	0.019 (2)
C16	0.042 (3)	0.066 (3)	0.068 (3)	0.007 (2)	0.020 (2)	0.006 (3)
C28	0.076 (4)	0.045 (3)	0.041 (2)	0.012 (2)	0.009 (2)	0.011 (2)
C215	0.098 (5)	0.043 (3)	0.068 (4)	0.006 (3)	−0.004 (3)	0.003 (3)
C115	0.153 (7)	0.049 (3)	0.065 (4)	0.034 (4)	−0.001 (4)	−0.002 (3)
C116	0.104 (5)	0.051 (3)	0.043 (3)	0.014 (3)	0.010 (3)	0.006 (2)

Geometric parameters (Å, º) top

Cl11—C113	1.737 (5)	C212—H212	0.9299
Cl31—C313	1.730 (5)	C39—C38	1.395 (6)
Cl21—C213	1.728 (5)	C18—C17	1.356 (7)
O12—C11	1.375 (5)	C18—H18	0.9300
O12—C12	1.384 (5)	C310—H310A	0.9700
C34—C35	1.398 (6)	C310—H310B	0.9700
C34—C39	1.398 (6)	C33—H33	0.9300
C34—C33	1.439 (6)	C211—C216	1.374 (7)
O32—C31	1.377 (5)	C211—C210	1.499 (7)
O32—C32	1.378 (5)	C17—C16	1.382 (8)
O22—C21	1.374 (6)	C17—H17	0.9299
O22—C22	1.394 (5)	C38—C37	1.369 (7)
C14—C15	1.395 (6)	C38—H38	0.9300
C14—C19	1.398 (6)	C312—C313	1.377 (6)
C14—C13	1.432 (6)	C312—H312	0.9300
C23—C22	1.311 (6)	C313—C314	1.365 (7)
C23—C24	1.422 (6)	C111—C116	1.366 (7)
C23—H23	0.9299	C26—C25	1.367 (7)
C19—C18	1.394 (6)	C26—C27	1.375 (8)
C19—C11	1.451 (6)	C26—H26	0.9301
C11—O11	1.197 (5)	C15—C16	1.381 (7)
O31—C31	1.199 (5)	C15—H15	0.9300
C31—C39	1.452 (6)	C210—H210A	0.9700
C29—C28	1.396 (7)	C210—H210B	0.9701
C29—C24	1.406 (6)	C214—C213	1.360 (7)
C29—C21	1.440 (7)	C214—C215	1.371 (8)
C35—C36	1.368 (7)	C214—H214	0.9301
C35—H35	0.9300	C316—C315	1.379 (8)
C24—C25	1.391 (7)	C316—H316	0.9300
O21—C21	1.211 (5)	C36—C37	1.378 (7)
C110—C12	1.498 (6)	C36—H36	0.9300
C110—C111	1.506 (6)	C114—C115	1.383 (8)
C110—H110A	0.9700	C114—H114	0.9300
C110—H110B	0.9699	C25—H25	0.9300
C32—C33	1.313 (6)	C27—C28	1.361 (8)
C32—C310	1.503 (6)	C27—H27	0.9299
C311—C312	1.379 (6)	C37—H37	0.9301
C311—C316	1.383 (7)	C315—C314	1.364 (8)
C311—C310	1.502 (6)	C315—H315	0.9299
C13—C12	1.315 (6)	C216—C215	1.383 (8)
C13—H13	0.9301	C216—H216	0.9300
C22—C210	1.500 (7)	C314—H314	0.9300
C113—C114	1.346 (7)	C16—H16	0.9300
C113—C112	1.372 (6)	C28—H28	0.9300
C112—C111	1.375 (7)	C215—H215	0.9301
C112—H112	0.9301	C115—C116	1.379 (8)
C212—C213	1.378 (7)	C115—H115	0.9299
C212—C211	1.388 (7)	C116—H116	0.9301

C11—O12—C12	122.6 (3)	C216—C211—C212	119.0 (4)
C35—C34—C39	118.9 (4)	C216—C211—C210	120.8 (5)
C35—C34—C33	123.0 (4)	C212—C211—C210	120.2 (5)
C39—C34—C33	118.0 (4)	C18—C17—C16	120.0 (5)
C31—O32—C32	122.6 (3)	C18—C17—H17	119.9
C21—O22—C22	122.0 (4)	C16—C17—H17	120.1
C15—C14—C19	118.3 (4)	C37—C38—C39	119.5 (4)
C15—C14—C13	122.7 (4)	C37—C38—H38	120.3
C19—C14—C13	119.0 (4)	C39—C38—H38	120.2
C22—C23—C24	121.3 (4)	C313—C312—C311	119.9 (4)
C22—C23—H23	119.3	C313—C312—H312	120.1
C24—C23—H23	119.4	C311—C312—H312	120.0
C18—C19—C14	120.6 (4)	C314—C313—C312	121.6 (5)
C18—C19—C11	120.0 (4)	C314—C313—Cl31	118.7 (4)
C14—C19—C11	119.4 (4)	C312—C313—Cl31	119.7 (4)
O11—C11—O12	116.5 (4)	C116—C111—C112	118.1 (5)
O11—C11—C19	126.5 (4)	C116—C111—C110	120.6 (5)
O12—C11—C19	117.0 (4)	C112—C111—C110	121.4 (4)
O31—C31—O32	116.6 (4)	C25—C26—C27	120.9 (5)
O31—C31—C39	126.7 (4)	C25—C26—H26	119.7
O32—C31—C39	116.6 (3)	C27—C26—H26	119.4
C28—C29—C24	120.2 (4)	C16—C15—C14	120.0 (5)
C28—C29—C21	120.3 (4)	C16—C15—H15	120.0
C24—C29—C21	119.4 (4)	C14—C15—H15	120.0
C36—C35—C34	119.7 (4)	C211—C210—C22	112.5 (4)
C36—C35—H35	120.2	C211—C210—H210A	109.4
C34—C35—H35	120.1	C22—C210—H210A	109.3
C25—C24—C29	118.0 (4)	C211—C210—H210B	108.9
C25—C24—C23	123.3 (4)	C22—C210—H210B	108.8
C29—C24—C23	118.7 (4)	H210A—C210—H210B	107.9
C12—C110—C111	112.5 (4)	C213—C214—C215	118.8 (5)
C12—C110—H110A	108.9	C213—C214—H214	120.7
C111—C110—H110A	109.0	C215—C214—H214	120.5
C12—C110—H110B	109.3	C315—C316—C311	120.4 (5)
C111—C110—H110B	109.3	C315—C316—H316	119.9
H110A—C110—H110B	107.8	C311—C316—H316	119.7
C33—C32—O32	121.5 (4)	C35—C36—C37	121.2 (5)
C33—C32—C310	129.2 (4)	C35—C36—H36	119.3
O32—C32—C310	109.3 (4)	C37—C36—H36	119.5
C312—C311—C316	118.5 (4)	C113—C114—C115	118.1 (5)
C312—C311—C310	120.7 (4)	C113—C114—H114	120.9
C316—C311—C310	120.8 (4)	C115—C114—H114	121.0
C12—C13—C14	120.7 (4)	C26—C25—C24	120.7 (5)
C12—C13—H13	119.6	C26—C25—H25	119.6
C14—C13—H13	119.6	C24—C25—H25	119.7
C23—C22—O22	120.9 (4)	C214—C213—C212	121.9 (5)
C23—C22—C210	129.5 (4)	C214—C213—Cl21	118.3 (4)
O22—C22—C210	109.6 (4)	C212—C213—Cl21	119.8 (4)
O21—C21—O22	115.7 (5)	C28—C27—C26	120.3 (5)
O21—C21—C29	126.7 (5)	C28—C27—H27	119.8
O22—C21—C29	117.6 (4)	C26—C27—H27	120.0
C114—C113—C112	121.4 (5)	C38—C37—C36	120.4 (4)
C114—C113—Cl11	118.4 (4)	C38—C37—H37	119.8
C112—C113—Cl11	120.2 (4)	C36—C37—H37	119.8
C113—C112—C111	121.1 (4)	C314—C315—C316	120.9 (5)
C113—C112—H112	119.5	C314—C315—H315	119.5
C111—C112—H112	119.4	C316—C315—H315	119.6
C213—C212—C211	119.3 (5)	C211—C216—C215	120.5 (5)
C213—C212—H212	120.4	C211—C216—H216	119.7
C211—C212—H212	120.3	C215—C216—H216	119.8
C13—C12—O12	121.1 (4)	C315—C314—C313	118.6 (5)
C13—C12—C110	129.7 (4)	C315—C314—H314	120.9
O12—C12—C110	109.2 (4)	C313—C314—H314	120.4
C38—C39—C34	120.3 (4)	C15—C16—C17	120.8 (5)
C38—C39—C31	119.4 (4)	C15—C16—H16	119.5
C34—C39—C31	120.3 (4)	C17—C16—H16	119.6
C17—C18—C19	120.2 (5)	C27—C28—C29	119.9 (5)
C17—C18—H18	119.8	C27—C28—H28	120.1
C19—C18—H18	120.0	C29—C28—H28	120.0
C311—C310—C32	113.3 (4)	C214—C215—C216	120.5 (5)
C311—C310—H310A	109.2	C214—C215—H215	119.9
C32—C310—H310A	109.0	C216—C215—H215	119.6
C311—C310—H310B	108.8	C116—C115—C114	120.9 (5)
C32—C310—H310B	108.6	C116—C115—H115	119.8
H310A—C310—H310B	107.7	C114—C115—H115	119.4
C32—C33—C34	121.0 (4)	C111—C116—C115	120.5 (5)
C32—C33—H33	119.5	C111—C116—H116	119.9
C34—C33—H33	119.5	C115—C116—H116	119.7

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C216—H216···O11	0.93	2.56	3.437 (6)	158
C116—H116···O21	0.93	2.58	3.396 (6)	147
C26—H26···O22ⁱ	0.93	2.45	3.339 (7)	161
C36—H36···O32ⁱ	0.93	2.52	3.409 (6)	160

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₁ClO₂
M_r	270.70
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	8.1411 (8), 15.0269 (14), 16.4080 (16)
α, β, γ (°)	91.696 (8), 98.478 (8), 102.624 (6)
V (Å³)	1933.4 (3)
Z	6
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.36 × 0.28 × 0.13

Data collection
Diffractometer	Bruker–Nonius KappaCCD area-detector diffractometer
Absorption correction	Integration (Gaussian; Coppens et al., 1970)
T_min, T_max	0.930, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	33806, 8770, 5387
R_int	0.096
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.093, 0.280, 1.15
No. of reflections	8770
No. of parameters	514
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.38

Computer programs: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C216—H216···O11	0.93	2.56	3.437 (6)	158.2
C116—H116···O21	0.93	2.58	3.396 (6)	146.9
C26—H26···O22ⁱ	0.93	2.45	3.339 (7)	160.5
C36—H36···O32ⁱ	0.93	2.52	3.409 (6)	159.7

Symmetry code: (i) x+1, y, z.

Acknowledgements

The authors gratefully acknowledge the financial support of the Ministry of Education of the Czech Republic (Project VZ0021627501) and the Higher Education Commission, Islamabad, Pakistan.

References

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