Methyl 5-chloro-2-hydr­oxy-3-(4-methoxy­phen­yl)-4,6-dimethyl­benzoate

Adeel, M.; Ali, I.; Langer, P.; Villinger, A.

doi:10.1107/S1600536809031614

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2176

doi:10.1107/S1600536809031614

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Methyl 5-chloro-2-hydroxy-3-(4-methoxyphenyl)-4,6-dimethylbenzoate

Muhammad Adeel,^a ^* Irshad Ali,^a Peter Langer ^b,^c and Alexander Villinger ^b

^aGomal University, Department of Chemistry, Dera Ismail Khan (NWFP), Pakistan, ^bUniversität Rostock, Institut für Chemie, Abteilung für Anorganische Chemie, Albert-Einstein-Strasse 3a, 18059 Rostock, Germany, and ^cLeibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock, Germany
^*Correspondence e-mail: muhammad_adeel2000@yahoo.com

(Received 23 July 2009; accepted 11 August 2009; online 19 August 2009)

In the title compound, C₁₇H₁₇ClO₄, the dihedral angle between the mean planes of the two benzene rings is 65.92 (5)°. The methyl ester group lies within the ring plane [deviations of O atoms from the plane = −0.051 (2) and 0.151 (2) Å] due to an intramolecular O—H⋯O hydrogen bond. In the crystal, molecules are held together by rather weak non-classical intermolecular C—H⋯O hydrogen bonds, resulting in dimeric units about inversion centers, forming eight- and ten-membered ring systems as R₂²(8) and R₂²(10) motifs.

Related literature

For the pharmacological relevance of 3-arylsalicylates, see: Buchanan et al. (1997 ); Huang et al. (1999 ); Lin, Lin & Kuo (1997 ); Lin, Wu & Kuo (1997 ). For the synthesis, see: Adeel et al. (2009 ); For hydrogen-bond motifs, see: Bernstein et al. (1994 ).

Experimental

Crystal data

C₁₇H₁₇ClO₄
M_r = 320.76
Triclinic, $[P \overline 1]$
a = 6.534 (4) Å
b = 9.574 (6) Å
c = 12.694 (8) Å
α = 97.420 (15)°
β = 100.56 (2)°
γ = 96.042 (14)°
V = 767.3 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 173 K
0.55 × 0.27 × 0.01 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.868, T_max = 0.997
14947 measured reflections
3964 independent reflections
3091 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.125
S = 1.09
3964 reflections
207 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.94 (2)	1.63 (2)	2.5061 (18)	153 (2)
C10—H10A⋯Cl1	0.98	2.45	3.003 (2)	115
C9—H9A⋯O2ⁱ	0.98	2.73	3.242 (3)	113
C15—H15⋯O4ⁱⁱ	0.95	2.50	3.437 (2)	170
Symmetry codes: (i) -x-1, -y+2, -z+1; (ii) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2003 ); cell refinement: SAINT (Bruker, 2003); 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 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2005 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809031614/pv2189sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809031614/pv2189Isup2.hkl

checkCIF report

Comment top

Functionalized biaryls containing a 3-arylsalicylate substructure occur in a variety of pharmacologically relevant natural products. The simple biaryls cynandione A—C have been isolated from many plant sources and show a considerable in vitro activity against hepatocytes, human bladder carcinoma T-24 cells, epidermoid carcinoma KB cells, and human hepatoma PLC/PRF/5 cells. For data on the pharmacological relevance of 3-arylsalicylates, see: Buchanan et al., (1997), Huang et al., (1999), Lin, Lin & Kuo (1997) and Lin, Wu & Kuo (1997). The sterically encumbered and functionalized biaryl, the title compound (I), was synthesized from 4-(4-methoxyphenyl)-1,3-bis(trimethylsilyloxy)-1,3-butadiene which is not readily available by other methods. In this paper, the crystal structure of (I) has been presented.

In the title compound (Fig. 1), the the dihedral angle between the mean planes of the two benzene rings is 65.92 (5)°. The methoxy group and the methylester group lie within the planes of the benzene rings to which they are bonded (deviation from mean planes: O2, -0.051 (2); O3, 0.151 (2); (??), 0.143 (2) Å; the torsion angles are: C2—C3—C8—O2 -174.47 (12) and C17—O4—C14—C15 -176.38 (12)°). There is an intramolecular hydrogen bond between the hydroxyl group and the carbonyl O atom of the methylester group. There are weak intramolecular interactions of the types C—H···O between atom O3 of the ester group and the adjacent methyl group (C10) and C—H···Cl between Cl1 and the adjacent methyl groups (C7/C10).

In the crystal structure, the molecules of (I) are held together by rather weak intermolecular C—H···O type non-classical hydrogen bonds resulting in dimeric units about inversion centers, forming eight and ten membered ring systems which may be described in terms of graph set notations (Bernstein et al. 1994) as R₂²(8) and R₂²(10) motifs for the hydrogen bonds: C15–H15···O4ⁱⁱ and C9–H9A···O2ⁱ, respectively (details are given in Table 1 and Figure 2); leading to a zigzag chain arrangement.

Related literature top

For the pharmacological relevance of 3-arylsalicylates, see: Buchanan et al. (1997); Huang et al. (1999); Lin, Lin & Kuo (1997); Lin, Wu & Kuo (1997). For the synthesis, see: Adeel et al. (2009); For hydrogen-bond motifs, see: Bernstein et al. (1994).

Experimental top

The title compound was prepared according to a previously published procedure (Adeel et al., 2009) using 3-chloro-4-trimethylsiloxy-pent-3-en-2-one (450 mg, 2.2 mmol), 4-(4-methoxyphenyl)-1,3-bis(silyloxy)-1,3-diene (806 mg, 2.2 mmol), and TiCl₄ (0.241 ml, 2.2 mmol). (I) was isolated as a colourless crystalline solid. Re-crystallization from a saturated dichloromethane/methanol (9:1) solution at ambient temperature gave colourless crystals suitable for crystallographic studies.

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I), showing the atomic numbering scheme and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Part of the packing diagram of (I). Unique O—H···O, C—H···O and C—H···Cl interactions represented by dashed lines are shown.

Methyl 5-chloro-2-hydroxy-3-(4-methoxyphenyl)-4,6-dimethylbenzoate top

Crystal data top

C₁₇H₁₇ClO₄	Z = 2
M_r = 320.76	F(000) = 336
Triclinic, P1	D_x = 1.388 Mg m⁻³
Hall symbol: -P 1	Melting point: 367 K
a = 6.534 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.574 (6) Å	Cell parameters from 7750 reflections
c = 12.694 (8) Å	θ = 6.4–59.5°
α = 97.420 (15)°	µ = 0.26 mm⁻¹
β = 100.56 (2)°	T = 173 K
γ = 96.042 (14)°	Plate, colourless
V = 767.3 (8) Å³	0.55 × 0.27 × 0.01 mm

Data collection top

Bruker APEXII CCD diffractometer	3964 independent reflections
Radiation source: sealed tube	3091 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω scans	θ_max = 29.0°, θ_min = 4.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −8→8
T_min = 0.868, T_max = 0.997	k = −13→13
14947 measured reflections	l = −17→17

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.073P)² + 0.0592P] where P = (F_o² + 2F_c²)/3
3964 reflections	(Δ/σ)_max < 0.001
207 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₇H₁₇ClO₄	γ = 96.042 (14)°
M_r = 320.76	V = 767.3 (8) Å³
Triclinic, P1	Z = 2
a = 6.534 (4) Å	Mo Kα radiation
b = 9.574 (6) Å	µ = 0.26 mm⁻¹
c = 12.694 (8) Å	T = 173 K
α = 97.420 (15)°	0.55 × 0.27 × 0.01 mm
β = 100.56 (2)°

Data collection top

Bruker APEXII CCD diffractometer	3964 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	3091 reflections with I > 2σ(I)
T_min = 0.868, T_max = 0.997	R_int = 0.024
14947 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.31 e Å⁻³
3964 reflections	Δρ_min = −0.23 e Å⁻³
207 parameters

Special details top

Experimental. Yield: 241 mg, 38%. m.p. = 367 (2) K. ¹H NMR (250 MHz, CDCl₃): δ = 2.10 (s, 3H, CH₃), 2.56 (s, 3H, CH₃), 3.77 (s, 3H, OCH₃), 3.89 (s, 3H, OCH₃), 6.89 (d, 2H, J = 8.8 Hz, ArH), 7.03 (d, 2H, J = 8.8 Hz, ArH), 10.54 (s, 1 H, OH). ¹³C NMR (62 MHz, CDCl₃): δ = 19.0, 19.4 (CH₃), 51.4, 54.2 (OCH₃), 111.5 (C), 112.9 (2 C, CH), 126.8, 127.6, 128.3 (C), 129.9 (2 C, CH), 135.3, 140.8, 156.1, 157.8 (C), 170.5 (C=O). IR (KBr, cm ^-1): ~ν = 3430 (m), 3050 (w), 3002 (w), 2959 (m), 2931 (m), 2837 (m), 1653 (s), 1607 (m), 1572 (w), 1514 (s), 1444 (s), 1373 (m), 1361 (s), 1297 (s), 1253 (s), 1220 (s), 1176 (m), 1092 (m), 1036 (m) 810 (m), 686 (m). GC—MS (EI, 70 eV): m/z (%): 322 (M⁺, ³⁷Cl, 16), 320 (M⁺, 47), 288 (100), 260 (11), 245 (27), 225 (29), 181 (7), 152 (12). HRMS (EI, 70 eV): calcd for C₁₇H₁₇O₄Cl [M, ³⁵Cl]: 320.08099; found 320.08088.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 3.7416 (0.0035) x + 4.8249 (0.0051) y - 7.9961 (0.0069) z = 2.4746 (0.0052)

* 0.0019 (0.0009) C1 * -0.0098 (0.0009) C2 * 0.0101 (0.0008) C3 * -0.0023 (0.0008) C4 * -0.0059 (0.0008) C5 * 0.0061 (0.0008) C6 0.0307 (0.0018) C8 - 0.0505 (0.0021) O2 0.1508 (0.0021) O3 0.1865 (0.0030) C9

Rms deviation of fitted atoms = 0.0068

3.1094 (0.0040) x + 6.1432 (0.0055) y - 9.0638 (0.0075) z = 4.7524 (0.0041)

Angle to previous plane (with approximate su) = 65.92 (0.05)

* 0.0117 (0.0009) C11 * -0.0089 (0.0009) C12 * -0.0016 (0.0009) C13 * 0.0091 (0.0009) C14 * -0.0060 (0.0010) C15 * -0.0043 (0.0010) C16 0.0476 (0.0018) O4 0.1434 (0.0024) C17

Rms deviation of fitted atoms = 0.0077

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 > 2σ(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
O1	−0.09153 (15)	0.87698 (10)	0.26779 (8)	0.0377 (2)
H1	−0.175 (3)	0.892 (2)	0.3196 (17)	0.067 (6)*
O2	−0.25708 (18)	0.99014 (12)	0.41459 (9)	0.0505 (3)
O3	−0.16796 (18)	1.21628 (12)	0.48417 (9)	0.0491 (3)
O4	0.23627 (16)	0.52864 (10)	−0.09022 (8)	0.0405 (2)
Cl1	0.48249 (6)	1.39934 (4)	0.30599 (3)	0.05110 (15)
C1	0.3067 (2)	1.24545 (14)	0.29830 (10)	0.0313 (3)
C2	0.1636 (2)	1.24546 (14)	0.36668 (10)	0.0310 (3)
C3	0.02086 (19)	1.11978 (13)	0.35519 (9)	0.0279 (3)
C4	0.03415 (19)	1.00141 (13)	0.27908 (10)	0.0272 (3)
C5	0.18323 (18)	1.00544 (13)	0.21221 (9)	0.0265 (3)
C6	0.32076 (19)	1.12961 (13)	0.22127 (9)	0.0282 (3)
C7	0.4785 (2)	1.14192 (16)	0.14895 (11)	0.0386 (3)
H7A	0.4538	1.0572	0.0937	0.058*
H7B	0.6207	1.1501	0.1925	0.058*
H7C	0.4637	1.2265	0.1136	0.058*
C8	−0.1451 (2)	1.10217 (14)	0.41965 (10)	0.0318 (3)
C9	−0.3311 (3)	1.20118 (19)	0.54694 (14)	0.0515 (4)
H9A	−0.4673	1.1710	0.4978	0.077*
H9B	−0.3346	1.2925	0.5910	0.077*
H9C	−0.3018	1.1298	0.5945	0.077*
C10	0.1683 (3)	1.37309 (18)	0.45028 (13)	0.0513 (4)
H10A	0.2995	1.4367	0.4576	0.077*
H10B	0.1599	1.3421	0.5202	0.077*
H10C	0.0487	1.4235	0.4275	0.077*
C11	0.18957 (19)	0.87662 (13)	0.13357 (9)	0.0277 (3)
C12	0.0254 (2)	0.82784 (14)	0.04645 (10)	0.0310 (3)
H12	−0.0962	0.8750	0.0389	0.037*
C13	0.0333 (2)	0.71183 (14)	−0.03026 (10)	0.0320 (3)
H13	−0.0805	0.6811	−0.0899	0.038*
C14	0.2094 (2)	0.64160 (13)	−0.01864 (10)	0.0312 (3)
C15	0.3732 (2)	0.68633 (15)	0.06955 (11)	0.0366 (3)
H15	0.4927	0.6372	0.0785	0.044*
C16	0.3628 (2)	0.80242 (15)	0.14448 (11)	0.0348 (3)
H16	0.4760	0.8322	0.2046	0.042*
C17	0.0787 (3)	0.48428 (16)	−0.18492 (11)	0.0427 (3)
H17A	−0.0537	0.4516	−0.1644	0.064*
H17B	0.1213	0.4064	−0.2306	0.064*
H17C	0.0596	0.5642	−0.2252	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0325 (5)	0.0332 (5)	0.0465 (5)	−0.0037 (4)	0.0149 (4)	−0.0005 (4)
O2	0.0459 (6)	0.0494 (7)	0.0592 (7)	−0.0045 (5)	0.0307 (5)	−0.0012 (5)
O3	0.0522 (7)	0.0473 (6)	0.0545 (6)	0.0061 (5)	0.0337 (5)	−0.0003 (5)
O4	0.0479 (6)	0.0350 (5)	0.0402 (5)	0.0133 (4)	0.0143 (4)	−0.0022 (4)
Cl1	0.0526 (3)	0.0427 (2)	0.0526 (2)	−0.01755 (17)	0.02060 (18)	−0.00782 (16)
C1	0.0298 (6)	0.0316 (7)	0.0294 (6)	−0.0037 (5)	0.0050 (5)	0.0013 (5)
C2	0.0305 (7)	0.0336 (7)	0.0270 (6)	0.0029 (5)	0.0054 (5)	−0.0007 (5)
C3	0.0247 (6)	0.0327 (6)	0.0268 (6)	0.0058 (5)	0.0056 (5)	0.0045 (5)
C4	0.0221 (6)	0.0296 (6)	0.0289 (6)	0.0029 (5)	0.0032 (4)	0.0039 (4)
C5	0.0236 (6)	0.0299 (6)	0.0256 (5)	0.0056 (5)	0.0030 (4)	0.0034 (4)
C6	0.0246 (6)	0.0345 (7)	0.0246 (5)	0.0022 (5)	0.0042 (4)	0.0040 (5)
C7	0.0358 (7)	0.0452 (8)	0.0354 (7)	−0.0010 (6)	0.0149 (6)	0.0024 (6)
C8	0.0274 (6)	0.0408 (7)	0.0293 (6)	0.0080 (6)	0.0074 (5)	0.0075 (5)
C9	0.0509 (9)	0.0617 (11)	0.0531 (9)	0.0171 (8)	0.0336 (8)	0.0092 (7)
C10	0.0572 (10)	0.0446 (9)	0.0485 (8)	−0.0076 (7)	0.0249 (7)	−0.0150 (7)
C11	0.0268 (6)	0.0287 (6)	0.0282 (6)	0.0045 (5)	0.0072 (5)	0.0032 (5)
C12	0.0291 (6)	0.0308 (6)	0.0325 (6)	0.0086 (5)	0.0040 (5)	0.0023 (5)
C13	0.0337 (7)	0.0318 (7)	0.0292 (6)	0.0058 (5)	0.0038 (5)	0.0016 (5)
C14	0.0370 (7)	0.0267 (6)	0.0336 (6)	0.0071 (5)	0.0152 (5)	0.0046 (5)
C15	0.0317 (7)	0.0418 (8)	0.0401 (7)	0.0154 (6)	0.0108 (6)	0.0061 (6)
C16	0.0274 (7)	0.0412 (8)	0.0348 (6)	0.0082 (6)	0.0038 (5)	0.0027 (5)
C17	0.0569 (9)	0.0345 (7)	0.0368 (7)	0.0054 (6)	0.0154 (6)	−0.0030 (5)

Geometric parameters (Å, º) top

O1—C4	1.3495 (17)	C7—H7C	0.9800
O1—H1	0.94 (2)	C9—H9A	0.9800
O2—C8	1.2205 (18)	C9—H9B	0.9800
O3—C8	1.3170 (18)	C9—H9C	0.9800
O3—C9	1.4496 (19)	C10—H10A	0.9800
O4—C14	1.3678 (16)	C10—H10B	0.9800
O4—C17	1.4169 (19)	C10—H10C	0.9800
Cl1—C1	1.7510 (16)	C11—C12	1.3850 (18)
C1—C2	1.3870 (19)	C11—C16	1.3937 (19)
C1—C6	1.4033 (18)	C12—C13	1.3914 (18)
C2—C3	1.417 (2)	C12—H12	0.9500
C2—C10	1.505 (2)	C13—C14	1.3869 (19)
C3—C4	1.4121 (18)	C13—H13	0.9500
C3—C8	1.4821 (19)	C14—C15	1.387 (2)
C4—C5	1.4052 (18)	C15—C16	1.382 (2)
C5—C6	1.3913 (19)	C15—H15	0.9500
C5—C11	1.4925 (18)	C16—H16	0.9500
C6—C7	1.5061 (19)	C17—H17A	0.9800
C7—H7A	0.9800	C17—H17B	0.9800
C7—H7B	0.9800	C17—H17C	0.9800

C4—O1—H1	104.4 (13)	O3—C9—H9C	109.5
C8—O3—C9	116.73 (12)	H9A—C9—H9C	109.5
C14—O4—C17	118.03 (11)	H9B—C9—H9C	109.5
C2—C1—C6	124.48 (12)	C2—C10—H10A	109.5
C2—C1—Cl1	118.94 (10)	C2—C10—H10B	109.5
C6—C1—Cl1	116.58 (10)	H10A—C10—H10B	109.5
C1—C2—C3	116.76 (12)	C2—C10—H10C	109.5
C1—C2—C10	120.28 (13)	H10A—C10—H10C	109.5
C3—C2—C10	122.94 (12)	H10B—C10—H10C	109.5
C4—C3—C2	119.62 (12)	C12—C11—C16	117.68 (12)
C4—C3—C8	116.31 (12)	C12—C11—C5	121.30 (11)
C2—C3—C8	124.06 (12)	C16—C11—C5	121.01 (11)
O1—C4—C5	115.99 (11)	C11—C12—C13	121.91 (12)
O1—C4—C3	122.28 (12)	C11—C12—H12	119.0
C5—C4—C3	121.72 (12)	C13—C12—H12	119.0
C6—C5—C4	118.97 (11)	C14—C13—C12	119.20 (12)
C6—C5—C11	121.90 (11)	C14—C13—H13	120.4
C4—C5—C11	119.13 (11)	C12—C13—H13	120.4
C5—C6—C1	118.42 (12)	O4—C14—C15	115.94 (12)
C5—C6—C7	121.32 (12)	O4—C14—C13	124.23 (12)
C1—C6—C7	120.25 (12)	C15—C14—C13	119.83 (12)
C6—C7—H7A	109.5	C16—C15—C14	120.05 (12)
C6—C7—H7B	109.5	C16—C15—H15	120.0
H7A—C7—H7B	109.5	C14—C15—H15	120.0
C6—C7—H7C	109.5	C15—C16—C11	121.29 (12)
H7A—C7—H7C	109.5	C15—C16—H16	119.4
H7B—C7—H7C	109.5	C11—C16—H16	119.4
O2—C8—O3	120.57 (12)	O4—C17—H17A	109.5
O2—C8—C3	123.38 (12)	O4—C17—H17B	109.5
O3—C8—C3	116.05 (12)	H17A—C17—H17B	109.5
O3—C9—H9A	109.5	O4—C17—H17C	109.5
O3—C9—H9B	109.5	H17A—C17—H17C	109.5
H9A—C9—H9B	109.5	H17B—C17—H17C	109.5

C6—C1—C2—C3	−1.3 (2)	Cl1—C1—C6—C7	−1.06 (16)
Cl1—C1—C2—C3	178.26 (9)	C9—O3—C8—O2	−0.3 (2)
C6—C1—C2—C10	177.07 (13)	C9—O3—C8—C3	179.38 (12)
Cl1—C1—C2—C10	−3.41 (19)	C4—C3—C8—O2	4.94 (19)
C1—C2—C3—C4	1.98 (18)	C2—C3—C8—O2	−174.47 (12)
C10—C2—C3—C4	−176.30 (12)	C4—C3—C8—O3	−174.73 (10)
C1—C2—C3—C8	−178.63 (11)	C2—C3—C8—O3	5.86 (19)
C10—C2—C3—C8	3.1 (2)	C6—C5—C11—C12	−113.50 (15)
C2—C3—C4—O1	177.11 (11)	C4—C5—C11—C12	66.49 (17)
C8—C3—C4—O1	−2.32 (17)	C6—C5—C11—C16	65.53 (17)
C2—C3—C4—C5	−1.34 (18)	C4—C5—C11—C16	−114.48 (14)
C8—C3—C4—C5	179.22 (10)	C16—C11—C12—C13	−2.1 (2)
O1—C4—C5—C6	−178.70 (10)	C5—C11—C12—C13	176.99 (12)
C3—C4—C5—C6	−0.15 (18)	C11—C12—C13—C14	0.9 (2)
O1—C4—C5—C11	1.31 (16)	C17—O4—C14—C15	−176.38 (12)
C3—C4—C5—C11	179.86 (10)	C17—O4—C14—C13	2.97 (19)
C4—C5—C6—C1	0.91 (17)	C12—C13—C14—O4	−178.45 (11)
C11—C5—C6—C1	−179.10 (10)	C12—C13—C14—C15	0.87 (19)
C4—C5—C6—C7	−177.74 (11)	O4—C14—C15—C16	178.07 (12)
C11—C5—C6—C7	2.25 (18)	C13—C14—C15—C16	−1.3 (2)
C2—C1—C6—C5	−0.19 (19)	C14—C15—C16—C11	0.0 (2)
Cl1—C1—C6—C5	−179.72 (9)	C12—C11—C16—C15	1.6 (2)
C2—C1—C6—C7	178.47 (12)	C5—C11—C16—C15	−177.44 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.94 (2)	1.63 (2)	2.5061 (18)	153 (2)
C7—H7C···Cl1	0.98	2.74	2.957 (2)	93
C10—H10A···Cl1	0.98	2.45	3.003 (2)	115
C10—H10B···O3	0.98	2.28	2.662 (2)	102
C10—H10C···O3	0.98	2.57	2.662 (2)	85
C9—H9A···O2ⁱ	0.98	2.73	3.242 (3)	113
C9—H9C···O2ⁱ	0.98	2.96	3.242 (3)	98
C15—H15···O4ⁱⁱ	0.95	2.50	3.437 (2)	170

Symmetry codes: (i) −x−1, −y+2, −z+1; (ii) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₇ClO₄
M_r	320.76
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	6.534 (4), 9.574 (6), 12.694 (8)
α, β, γ (°)	97.420 (15), 100.56 (2), 96.042 (14)
V (Å³)	767.3 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.55 × 0.27 × 0.01

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.868, 0.997
No. of measured, independent and observed [I > 2σ(I)] reflections	14947, 3964, 3091
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.125, 1.09
No. of reflections	3964
No. of parameters	207
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.23

Computer programs: APEX2 (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2005).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.94 (2)	1.63 (2)	2.5061 (18)	153 (2)
C7—H7C···Cl1	0.98	2.74	2.957 (2)	93
C10—H10A···Cl1	0.98	2.45	3.003 (2)	115
C10—H10B···O3	0.98	2.28	2.662 (2)	102
C10—H10C···O3	0.98	2.57	2.662 (2)	85
C9—H9A···O2ⁱ	0.98	2.73	3.242 (3)	113
C9—H9C···O2ⁱ	0.98	2.96	3.242 (3)	98
C15—H15···O4ⁱⁱ	0.95	2.50	3.437 (2)	170

Symmetry codes: (i) −x−1, −y+2, −z+1; (ii) −x+1, −y+1, −z.

Acknowledgements

Financial support for MA from the Higher Education Commission of Pakistan (HEC) under the IPFP programe is gratefully acknowledged.

References

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