5-(Chloro­meth­yl)quinolin-8-yl acetate

Kong, L.-Q.; Qiao, Y.; Zhang, J.-D.

doi:10.1107/S1600536808021788

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1519

doi:10.1107/S1600536808021788

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5-(Chloromethyl)quinolin-8-yl acetate

Ling-Qian Kong,^a ^* Yan Qiao ^a and Ji-Dong Zhang ^a

^aDongchang College, Liaocheng University, Liaocheng 250059, People's Republic of China
^*Correspondence e-mail: konglingqian08@163.com

(Received 4 July 2008; accepted 13 July 2008; online 19 July 2008)

The title compound, C₁₂H₁₀ClNO₂, crystallizes with two independent molecules in the asymmetric unit; these are approximate mirror images of each other. In each molecule, the chloromethyl and acetate groups lie on the same side of the quinoline ring system, with dihedral angles between the ring plane and the plane of the acetate group of 82.0 (1) and −79.2 (1)°. The C—C—C—Cl torsion angles for the chloromethyl groups of the two molecules are 80.9 (2) and −83.1 (2)°.

Related literature

For related literature, see: Chen & Shi (1998 ); Marian (1966 ).

Experimental

Crystal data

C₁₂H₁₀ClNO₂
M_r = 235.66
Triclinic, $[P \overline 1]$
a = 9.2299 (10) Å
b = 11.0042 (13) Å
c = 11.2429 (13) Å
α = 105.073 (4)°
β = 94.105 (1)°
γ = 90.815 (2)°
V = 1099.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 295 K
0.22 × 0.18 × 0.16 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.931, T_max = 0.949
5721 measured reflections
3843 independent reflections
3247 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.096
S = 1.04
3843 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808021788/bi2295sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808021788/bi2295Isup2.hkl

checkCIF report

Comment top

8-Hydroxyquinoline and its derivatives are amongst the most extensively investigated ligands in coordination chemistry (Chen & Shi, 1998). In the course of our studies on 8-hydroxyquinoline derivatives, we have synthesised the title compound, which is a key intermediate in the synthesis of 8-hydroxyquinoline derivatives.

Related literature top

For related literature, see: Chen & Shi (1998); Marian (1966).

Experimental top

5-(Chloromethyl)quinolin-8-ol hydrochloride (0.0217 mol) (Marian, 1966) and acetic anhydride (25 ml) were added to a 100 ml flask, and refluxed for 6 h. After cooling to room temperature, the mixture was poured into cool water (500 ml). The precipitate was washed with a large amount of water, collected by filtration, and dried to produce the title compound as a grey solid. Colourless single crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of an ethanol solution over a period of 2 d.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Two independent molecules in the title compound, with displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted.

5-(Chloromethyl)quinolin-8-yl acetate top

Crystal data top

C₁₂H₁₀ClNO₂	Z = 4
M_r = 235.66	F(000) = 488
Triclinic, P1	D_x = 1.424 Mg m⁻³
Hall symbol: -P 1	Melting point: 400 K
a = 9.2299 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.0042 (13) Å	Cell parameters from 3502 reflections
c = 11.2429 (13) Å	θ = 2.2–28.2°
α = 105.073 (4)°	µ = 0.33 mm⁻¹
β = 94.105 (1)°	T = 295 K
γ = 90.815 (2)°	Block, colorless
V = 1099.2 (2) Å³	0.22 × 0.18 × 0.16 mm

Data collection top

Bruker SMART CCD diffractometer	3843 independent reflections
Radiation source: fine-focus sealed tube	3247 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
ϕ and ω scans	θ_max = 25.1°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.931, T_max = 0.949	k = −12→13
5721 measured reflections	l = −12→13

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0471P)² + 0.3054P] where P = (F_o² + 2F_c²)/3
3843 reflections	(Δ/σ)_max = 0.001
289 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₂H₁₀ClNO₂	γ = 90.815 (2)°
M_r = 235.66	V = 1099.2 (2) Å³
Triclinic, P1	Z = 4
a = 9.2299 (10) Å	Mo Kα radiation
b = 11.0042 (13) Å	µ = 0.33 mm⁻¹
c = 11.2429 (13) Å	T = 295 K
α = 105.073 (4)°	0.22 × 0.18 × 0.16 mm
β = 94.105 (1)°

Data collection top

Bruker SMART CCD diffractometer	3843 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3247 reflections with I > 2σ(I)
T_min = 0.931, T_max = 0.949	R_int = 0.015
5721 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.04	Δρ_max = 0.19 e Å⁻³
3843 reflections	Δρ_min = −0.21 e Å⁻³
289 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
Cl1	0.45143 (5)	0.67427 (5)	0.57622 (4)	0.05362 (15)
Cl2	−0.04871 (6)	0.86602 (4)	0.57393 (5)	0.05615 (16)
O1	0.52846 (13)	1.00138 (12)	0.17138 (11)	0.0470 (3)
O2	0.74973 (16)	1.02523 (15)	0.27180 (14)	0.0658 (4)
O3	0.03984 (14)	0.32842 (11)	0.17193 (12)	0.0491 (3)
O4	0.25535 (16)	0.36297 (15)	0.28101 (15)	0.0665 (4)
N1	0.60339 (17)	0.75273 (15)	0.11659 (13)	0.0479 (4)
N2	0.11712 (16)	0.54988 (15)	0.11822 (13)	0.0459 (4)
C1	0.6356 (2)	0.6329 (2)	0.09146 (18)	0.0565 (5)
H1	0.6942	0.6023	0.0270	0.068*
C2	0.5871 (2)	0.54890 (18)	0.15594 (19)	0.0566 (5)
H2	0.6132	0.4652	0.1338	0.068*
C3	0.5019 (2)	0.59019 (17)	0.25069 (17)	0.0478 (4)
H3	0.4689	0.5351	0.2938	0.057*
C4	0.46384 (17)	0.71804 (15)	0.28332 (15)	0.0376 (4)
C5	0.37582 (18)	0.77105 (17)	0.38191 (15)	0.0400 (4)
C6	0.3457 (2)	0.89608 (18)	0.40698 (17)	0.0472 (4)
H6	0.2883	0.9305	0.4713	0.057*
C7	0.3996 (2)	0.97351 (17)	0.33765 (17)	0.0471 (4)
H7	0.3782	1.0584	0.3562	0.057*
C8	0.48297 (18)	0.92409 (16)	0.24364 (15)	0.0393 (4)
C9	0.51836 (17)	0.79539 (16)	0.21255 (15)	0.0374 (4)
C10	0.3155 (2)	0.6929 (2)	0.45894 (18)	0.0502 (5)
H10A	0.2836	0.6108	0.4065	0.060*
H10B	0.2319	0.7332	0.4979	0.060*
C11	0.6674 (2)	1.04787 (17)	0.19412 (17)	0.0462 (4)
C12	0.6965 (3)	1.1301 (2)	0.1117 (2)	0.0681 (6)
H12A	0.6399	1.2041	0.1332	0.102*
H12B	0.6704	1.0851	0.0274	0.102*
H12C	0.7979	1.1542	0.1213	0.102*
C13	0.1446 (2)	0.6560 (2)	0.09004 (18)	0.0542 (5)
H13	0.2051	0.6536	0.0268	0.065*
C14	0.0896 (2)	0.7722 (2)	0.14814 (19)	0.0557 (5)
H14	0.1119	0.8437	0.1226	0.067*
C15	0.0033 (2)	0.77951 (17)	0.24219 (17)	0.0485 (4)
H15	−0.0332	0.8563	0.2826	0.058*
C16	−0.03079 (17)	0.66915 (16)	0.27844 (15)	0.0382 (4)
C17	−0.11980 (18)	0.66651 (17)	0.37671 (16)	0.0418 (4)
C18	−0.1492 (2)	0.55457 (19)	0.40301 (17)	0.0502 (5)
H18	−0.2071	0.5533	0.4671	0.060*
C19	−0.0938 (2)	0.44153 (18)	0.33514 (17)	0.0490 (4)
H19	−0.1159	0.3661	0.3535	0.059*
C20	−0.00775 (18)	0.44301 (16)	0.24263 (16)	0.0411 (4)
C21	0.02808 (17)	0.55580 (16)	0.21112 (14)	0.0373 (4)
C22	−0.1815 (2)	0.78404 (19)	0.45259 (18)	0.0527 (5)
H22A	−0.2676	0.7626	0.4887	0.063*
H22B	−0.2098	0.8385	0.4001	0.063*
C23	0.1777 (2)	0.29749 (18)	0.19924 (18)	0.0472 (4)
C24	0.2111 (3)	0.1743 (2)	0.1156 (2)	0.0684 (6)
H24A	0.2125	0.1823	0.0326	0.103*
H24B	0.1380	0.1123	0.1183	0.103*
H24C	0.3044	0.1486	0.1417	0.103*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0594 (3)	0.0552 (3)	0.0514 (3)	−0.0014 (2)	−0.0012 (2)	0.0249 (2)
Cl2	0.0605 (3)	0.0447 (3)	0.0550 (3)	0.0013 (2)	0.0009 (2)	−0.0007 (2)
O1	0.0496 (7)	0.0482 (7)	0.0475 (7)	−0.0055 (6)	−0.0013 (6)	0.0223 (6)
O2	0.0525 (8)	0.0773 (10)	0.0691 (9)	−0.0129 (7)	−0.0105 (7)	0.0268 (8)
O3	0.0510 (7)	0.0381 (7)	0.0513 (7)	0.0055 (5)	−0.0045 (6)	0.0015 (5)
O4	0.0501 (8)	0.0702 (10)	0.0749 (10)	0.0054 (7)	−0.0100 (7)	0.0154 (8)
N1	0.0495 (9)	0.0516 (9)	0.0409 (8)	0.0002 (7)	0.0078 (7)	0.0081 (7)
N2	0.0447 (8)	0.0536 (9)	0.0374 (8)	0.0020 (7)	0.0028 (6)	0.0082 (7)
C1	0.0581 (12)	0.0583 (13)	0.0464 (11)	0.0065 (10)	0.0095 (9)	0.0000 (9)
C2	0.0626 (13)	0.0410 (10)	0.0609 (12)	0.0075 (9)	0.0013 (10)	0.0043 (9)
C3	0.0507 (11)	0.0403 (10)	0.0521 (11)	−0.0017 (8)	−0.0036 (9)	0.0140 (8)
C4	0.0341 (8)	0.0393 (9)	0.0383 (8)	−0.0027 (7)	−0.0046 (7)	0.0105 (7)
C5	0.0329 (9)	0.0483 (10)	0.0406 (9)	−0.0023 (7)	−0.0018 (7)	0.0161 (8)
C6	0.0464 (10)	0.0529 (11)	0.0434 (10)	0.0076 (8)	0.0101 (8)	0.0124 (8)
C7	0.0525 (11)	0.0387 (9)	0.0500 (10)	0.0065 (8)	0.0045 (8)	0.0110 (8)
C8	0.0389 (9)	0.0414 (9)	0.0390 (9)	−0.0044 (7)	−0.0031 (7)	0.0150 (7)
C9	0.0345 (9)	0.0417 (9)	0.0344 (8)	−0.0029 (7)	−0.0029 (7)	0.0090 (7)
C10	0.0404 (10)	0.0624 (12)	0.0529 (11)	−0.0043 (8)	0.0020 (8)	0.0247 (9)
C11	0.0500 (11)	0.0407 (10)	0.0449 (10)	−0.0059 (8)	0.0058 (9)	0.0054 (8)
C12	0.0832 (16)	0.0607 (13)	0.0636 (13)	−0.0206 (11)	0.0130 (12)	0.0212 (11)
C13	0.0519 (11)	0.0681 (14)	0.0444 (10)	−0.0022 (10)	0.0078 (9)	0.0171 (9)
C14	0.0616 (12)	0.0541 (12)	0.0553 (12)	−0.0078 (9)	0.0003 (10)	0.0231 (10)
C15	0.0516 (11)	0.0388 (10)	0.0530 (11)	0.0007 (8)	−0.0022 (9)	0.0103 (8)
C16	0.0338 (8)	0.0393 (9)	0.0379 (9)	−0.0004 (7)	−0.0052 (7)	0.0060 (7)
C17	0.0352 (9)	0.0435 (10)	0.0423 (9)	0.0017 (7)	−0.0002 (7)	0.0044 (7)
C18	0.0477 (11)	0.0554 (11)	0.0463 (10)	−0.0038 (8)	0.0102 (8)	0.0095 (9)
C19	0.0541 (11)	0.0433 (10)	0.0509 (10)	−0.0041 (8)	0.0037 (9)	0.0149 (8)
C20	0.0403 (9)	0.0363 (9)	0.0420 (9)	0.0025 (7)	−0.0052 (7)	0.0041 (7)
C21	0.0315 (8)	0.0426 (9)	0.0347 (8)	0.0008 (7)	−0.0042 (7)	0.0062 (7)
C22	0.0436 (10)	0.0556 (12)	0.0526 (11)	0.0065 (8)	0.0040 (8)	0.0022 (9)
C23	0.0489 (11)	0.0473 (10)	0.0504 (11)	0.0072 (8)	0.0062 (9)	0.0207 (9)
C24	0.0816 (16)	0.0563 (13)	0.0728 (14)	0.0253 (11)	0.0222 (12)	0.0209 (11)

Geometric parameters (Å, º) top

Cl1—C10	1.8072 (19)	C10—H10A	0.970
Cl2—C22	1.807 (2)	C10—H10B	0.970
O1—C11	1.356 (2)	C11—C12	1.488 (3)
O1—C8	1.399 (2)	C12—H12A	0.960
O2—C11	1.194 (2)	C12—H12B	0.960
O3—C23	1.357 (2)	C12—H12C	0.960
O3—C20	1.400 (2)	C13—C14	1.397 (3)
O4—C23	1.193 (2)	C13—H13	0.930
N1—C1	1.318 (3)	C14—C15	1.355 (3)
N1—C9	1.367 (2)	C14—H14	0.930
N2—C13	1.313 (3)	C15—C16	1.416 (3)
N2—C21	1.364 (2)	C15—H15	0.930
C1—C2	1.402 (3)	C16—C21	1.418 (2)
C1—H1	0.930	C16—C17	1.429 (2)
C2—C3	1.356 (3)	C17—C18	1.367 (3)
C2—H2	0.930	C17—C22	1.497 (2)
C3—C4	1.415 (2)	C18—C19	1.404 (3)
C3—H3	0.930	C18—H18	0.930
C4—C9	1.417 (2)	C19—C20	1.356 (3)
C4—C5	1.427 (2)	C19—H19	0.930
C5—C6	1.367 (3)	C20—C21	1.417 (2)
C5—C10	1.497 (2)	C22—H22A	0.970
C6—C7	1.404 (3)	C22—H22B	0.970
C6—H6	0.930	C23—C24	1.486 (3)
C7—C8	1.354 (2)	C24—H24A	0.960
C7—H7	0.930	C24—H24B	0.960
C8—C9	1.417 (2)	C24—H24C	0.960

C11—O1—C8	117.15 (14)	H12A—C12—H12C	109.5
C23—O3—C20	117.00 (14)	H12B—C12—H12C	109.5
C1—N1—C9	116.68 (16)	N2—C13—C14	124.74 (18)
C13—N2—C21	116.52 (16)	N2—C13—H13	117.6
N1—C1—C2	123.99 (18)	C14—C13—H13	117.6
N1—C1—H1	118.0	C15—C14—C13	119.15 (19)
C2—C1—H1	118.0	C15—C14—H14	120.4
C3—C2—C1	119.73 (18)	C13—C14—H14	120.4
C3—C2—H2	120.1	C14—C15—C16	119.46 (18)
C1—C2—H2	120.1	C14—C15—H15	120.3
C2—C3—C4	119.31 (18)	C16—C15—H15	120.3
C2—C3—H3	120.3	C15—C16—C21	116.61 (16)
C4—C3—H3	120.3	C15—C16—C17	123.98 (16)
C9—C4—C3	116.66 (16)	C21—C16—C17	119.42 (16)
C9—C4—C5	119.63 (15)	C18—C17—C16	119.63 (16)
C3—C4—C5	123.71 (16)	C18—C17—C22	118.87 (17)
C6—C5—C4	119.42 (16)	C16—C17—C22	121.50 (17)
C6—C5—C10	119.06 (16)	C17—C18—C19	121.30 (17)
C4—C5—C10	121.51 (16)	C17—C18—H18	119.4
C5—C6—C7	121.35 (16)	C19—C18—H18	119.4
C5—C6—H6	119.3	C20—C19—C18	119.64 (18)
C7—C6—H6	119.3	C20—C19—H19	120.2
C8—C7—C6	119.72 (17)	C18—C19—H19	120.2
C8—C7—H7	120.1	C19—C20—O3	118.62 (16)
C6—C7—H7	120.1	C19—C20—C21	122.02 (16)
C7—C8—O1	118.65 (16)	O3—C20—C21	119.26 (15)
C7—C8—C9	121.91 (16)	N2—C21—C20	118.54 (15)
O1—C8—C9	119.34 (15)	N2—C21—C16	123.49 (16)
N1—C9—C4	123.63 (16)	C20—C21—C16	117.98 (15)
N1—C9—C8	118.41 (15)	C17—C22—Cl2	110.29 (13)
C4—C9—C8	117.96 (15)	C17—C22—H22A	109.6
C5—C10—Cl1	110.54 (12)	Cl2—C22—H22A	109.6
C5—C10—H10A	109.5	C17—C22—H22B	109.6
Cl1—C10—H10A	109.5	Cl2—C22—H22B	109.6
C5—C10—H10B	109.5	H22A—C22—H22B	108.1
Cl1—C10—H10B	109.5	O4—C23—O3	122.23 (17)
H10A—C10—H10B	108.1	O4—C23—C24	127.61 (19)
O2—C11—O1	122.74 (17)	O3—C23—C24	110.15 (18)
O2—C11—C12	127.10 (19)	C23—C24—H24A	109.5
O1—C11—C12	110.15 (17)	C23—C24—H24B	109.5
C11—C12—H12A	109.5	H24A—C24—H24B	109.5
C11—C12—H12B	109.5	C23—C24—H24C	109.5
H12A—C12—H12B	109.5	H24A—C24—H24C	109.5
C11—C12—H12C	109.5	H24B—C24—H24C	109.5

C9—N1—C1—C2	0.6 (3)	C21—N2—C13—C14	0.0 (3)
N1—C1—C2—C3	−0.2 (3)	N2—C13—C14—C15	1.2 (3)
C1—C2—C3—C4	−0.3 (3)	C13—C14—C15—C16	−0.8 (3)
C2—C3—C4—C9	0.2 (2)	C14—C15—C16—C21	−0.7 (2)
C2—C3—C4—C5	−179.53 (17)	C14—C15—C16—C17	179.58 (17)
C9—C4—C5—C6	−0.2 (2)	C15—C16—C17—C18	178.55 (17)
C3—C4—C5—C6	179.55 (16)	C21—C16—C17—C18	−1.2 (2)
C9—C4—C5—C10	179.84 (15)	C15—C16—C17—C22	−1.8 (3)
C3—C4—C5—C10	−0.4 (2)	C21—C16—C17—C22	178.48 (15)
C4—C5—C6—C7	0.0 (3)	C16—C17—C18—C19	−0.1 (3)
C10—C5—C6—C7	179.96 (17)	C22—C17—C18—C19	−179.78 (17)
C5—C6—C7—C8	0.2 (3)	C17—C18—C19—C20	0.9 (3)
C6—C7—C8—O1	176.36 (15)	C18—C19—C20—O3	−176.61 (16)
C6—C7—C8—C9	−0.1 (3)	C18—C19—C20—C21	−0.3 (3)
C11—O1—C8—C7	102.11 (19)	C23—O3—C20—C19	−100.93 (19)
C11—O1—C8—C9	−81.32 (19)	C23—O3—C20—C21	82.69 (19)
C1—N1—C9—C4	−0.6 (3)	C13—N2—C21—C20	178.39 (16)
C1—N1—C9—C8	179.11 (16)	C13—N2—C21—C16	−1.7 (2)
C3—C4—C9—N1	0.2 (2)	C19—C20—C21—N2	178.97 (16)
C5—C4—C9—N1	180.00 (15)	O3—C20—C21—N2	−4.8 (2)
C3—C4—C9—C8	−179.53 (15)	C19—C20—C21—C16	−0.9 (2)
C5—C4—C9—C8	0.3 (2)	O3—C20—C21—C16	175.30 (14)
C7—C8—C9—N1	−179.84 (16)	C15—C16—C21—N2	2.0 (2)
O1—C8—C9—N1	3.7 (2)	C17—C16—C21—N2	−178.21 (15)
C7—C8—C9—C4	−0.1 (2)	C15—C16—C21—C20	−178.08 (15)
O1—C8—C9—C4	−176.54 (14)	C17—C16—C21—C20	1.7 (2)
C6—C5—C10—Cl1	−99.09 (17)	C18—C17—C22—Cl2	96.61 (18)
C4—C5—C10—Cl1	80.86 (18)	C16—C17—C22—Cl2	−83.08 (19)
C8—O1—C11—O2	0.1 (3)	C20—O3—C23—O4	1.3 (3)
C8—O1—C11—C12	−178.64 (16)	C20—O3—C23—C24	−179.61 (16)

Experimental details

Crystal data
Chemical formula	C₁₂H₁₀ClNO₂
M_r	235.66
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	9.2299 (10), 11.0042 (13), 11.2429 (13)
α, β, γ (°)	105.073 (4), 94.105 (1), 90.815 (2)
V (Å³)	1099.2 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.22 × 0.18 × 0.16

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.931, 0.949
No. of measured, independent and observed [I > 2σ(I)] reflections	5721, 3843, 3247
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.096, 1.04
No. of reflections	3843
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.21

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This project was supported by the Foundation of Dongchang College, Liaocheng University (grant No. LG0801).

References

Chen, C. H. & Shi, J. M. (1998). Coord. Chem. Rev. 171, 161–174. Web of Science CrossRef CAS Google Scholar
Marian, K. (1966). J. Heterocycl. Chem. 3, 275–277. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar