9,9-Bis[4-(2-chloro­eth­oxy)phen­yl]-9H-fluorene

Shah, K.; Raza Shah, M.; Khan, I.U.; Ng, S.W.

doi:10.1107/S1600536810032046

organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page o2317

https://doi.org/10.1107/S1600536810032046

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9,9-Bis[4-(2-chloroethoxy)phenyl]-9H-fluorene

Kiramat Shah,^a Muhammad Raza Shah,^a Islam Ullah Khan ^b and Seik Weng Ng ^c ^*

^aH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan, ^bDepartment of Chemistry, Government College University, 54000 Lahore, Pakistan, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 5 August 2010; accepted 10 August 2010; online 18 August 2010)

The title compound, C₂₉H₂₄Cl₂O₂, a fluorene derivative, features a C atom that is connected to four phenylene rings, two of which are almost coplanar (r.m.s. deviation = 0.035 Å) as they belong to the fluorene system. The other two rings are aligned at angles of 67.5 (5) and 85.5 (5)° with respect to the pair. The O and Cl atoms of the –OCH₂CH₂Cl– units adopt a gauche conformation [torsion angles = 61.6 (6) and 66.6 (5)°].

Related literature

For related structures, see: Shah et al. (2010a ,b ).

Experimental

Crystal data

C₂₉H₂₄Cl₂O₂
M_r = 475.38
Monoclinic, P 2₁ /c
a = 12.2334 (7) Å
b = 10.8063 (6) Å
c = 19.0374 (12) Å
β = 108.172 (2)°
V = 2391.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 293 K
0.27 × 0.15 × 0.07 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.783, T_max = 0.862
18388 measured reflections
4206 independent reflections
2326 reflections with I > 2σ(I)
R_int = 0.062

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.177
S = 1.01
4206 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.66 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810032046/nk2052sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810032046/nk2052Isup2.hkl

checkCIF report

Comment top

We are interested in V-shaped molecules; in the title compound, the kink is provided by the carbon atom of the fluorene system that is also connected to two other aromatic rings having para substituents (Scheme I). The compound is synthesized from 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene, a commerically available reagent. The compound features a carbon atom that is connected to four phenylene rings, two of which are coplanar as these belong the the fluorene system (Fig. 1). The other two rings are aligned at angles of 67.5 (5) and 85.5 (5) ° with respect to the pair. The oxygen and chlorine atoms of the –OCH₂CH₂Cl– units adopt a gauche conformation [torsion angles 61.6 (6). 66.6 (5) °].

Related literature top

For related structures, see: Shah et al. (2010a,b).

Experimental top

9,9-Bis[4-(2-hydroxyethoxy)phenyl]fluorene (0.5 g, 3.5 mmol) was dissolved in dichloromethane (20 ml) to give a clear solution.Thionyl chloride (5 ml) along with two drops of N,N-dimethylformamide (to serve as catalyst) were added. The mixture was heated for 12 h. Aqueous ammonium hydroxide was added and the precipitated product was was extracted with dichloromethane. The compound was recrystallized from dichloromethane/hexane (7:3).

Structure description top

For related structures, see: Shah et al. (2010a,b).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₂₉H₂₄Cl₂O₂ at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

9,9-Bis[4-(2-chloroethoxy)phenyl]-9H-fluorene top

Crystal data top

C₂₉H₂₄Cl₂O₂	F(000) = 992
M_r = 475.38	D_x = 1.321 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2267 reflections
a = 12.2334 (7) Å	θ = 2.3–21.1°
b = 10.8063 (6) Å	µ = 0.30 mm⁻¹
c = 19.0374 (12) Å	T = 293 K
β = 108.172 (2)°	Wedge, colourless
V = 2391.2 (2) Å³	0.27 × 0.15 × 0.07 mm
Z = 4

Data collection top

Bruker Kappa APEXII diffractometer	4206 independent reflections
Radiation source: fine-focus sealed tube	2326 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
φ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→10
T_min = 0.783, T_max = 0.862	k = −12→11
18388 measured reflections	l = −22→22

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.177	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0687P)² + 1.9561P] where P = (F_o² + 2F_c²)/3
4206 reflections	(Δ/σ)_max = 0.001
298 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.66 e Å⁻³

Crystal data top

C₂₉H₂₄Cl₂O₂	V = 2391.2 (2) Å³
M_r = 475.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.2334 (7) Å	µ = 0.30 mm⁻¹
b = 10.8063 (6) Å	T = 293 K
c = 19.0374 (12) Å	0.27 × 0.15 × 0.07 mm
β = 108.172 (2)°

Data collection top

Bruker Kappa APEXII diffractometer	4206 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2326 reflections with I > 2σ(I)
T_min = 0.783, T_max = 0.862	R_int = 0.062
18388 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.177	H-atom parameters constrained
S = 1.01	Δρ_max = 0.53 e Å⁻³
4206 reflections	Δρ_min = −0.66 e Å⁻³
298 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.99333 (10)	0.53514 (15)	0.63783 (7)	0.0941 (5)
Cl2	0.08864 (16)	−0.1721 (2)	0.48114 (9)	0.1541 (9)
O1	0.7730 (2)	0.4956 (3)	0.50972 (15)	0.0763 (9)
O2	0.1404 (2)	−0.0587 (2)	0.34783 (15)	0.0596 (7)
C1	0.9155 (5)	0.6374 (5)	0.5696 (3)	0.0966 (18)
H1A	0.8605	0.6808	0.5879	0.116*
H1B	0.9681	0.6984	0.5611	0.116*
C2	0.8516 (4)	0.5776 (5)	0.4969 (2)	0.0719 (13)
H2A	0.8121	0.6400	0.4614	0.086*
H2B	0.9049	0.5340	0.4771	0.086*
C3	0.6879 (3)	0.4493 (3)	0.4503 (2)	0.0510 (10)
C4	0.6872 (3)	0.4561 (3)	0.3780 (2)	0.0489 (9)
H4	0.7507	0.4867	0.3667	0.059*
C5	0.5904 (3)	0.4167 (3)	0.32219 (19)	0.0414 (9)
H5	0.5901	0.4216	0.2733	0.050*
C6	0.4953 (3)	0.3708 (3)	0.33692 (18)	0.0372 (8)
C7	0.5013 (3)	0.3592 (4)	0.4106 (2)	0.0570 (11)
H7	0.4396	0.3251	0.4226	0.068*
C8	0.5967 (4)	0.3971 (4)	0.4659 (2)	0.0638 (12)
H8	0.5993	0.3870	0.5149	0.077*
C9	0.3808 (3)	0.3497 (3)	0.27615 (17)	0.0355 (8)
C10	0.3941 (3)	0.3372 (3)	0.19901 (18)	0.0373 (8)
C11	0.4475 (3)	0.2442 (3)	0.1722 (2)	0.0506 (10)
H11	0.4818	0.1778	0.2020	0.061*
C12	0.4487 (4)	0.2521 (4)	0.0999 (2)	0.0658 (12)
H12	0.4834	0.1895	0.0808	0.079*
C13	0.3997 (4)	0.3504 (4)	0.0559 (2)	0.0713 (13)
H13	0.4015	0.3535	0.0074	0.086*
C14	0.3478 (4)	0.4450 (4)	0.0825 (2)	0.0609 (11)
H14	0.3150	0.5121	0.0528	0.073*
C15	0.3458 (3)	0.4375 (3)	0.15460 (19)	0.0426 (9)
C16	0.2981 (3)	0.5234 (3)	0.19711 (19)	0.0411 (8)
C17	0.2481 (3)	0.6392 (4)	0.1796 (2)	0.0570 (11)
H17	0.2381	0.6741	0.1334	0.068*
C18	0.2135 (3)	0.7017 (4)	0.2324 (3)	0.0632 (12)
H18	0.1802	0.7795	0.2213	0.076*
C19	0.2272 (3)	0.6516 (3)	0.3004 (3)	0.0585 (11)
H19	0.2022	0.6950	0.3347	0.070*
C20	0.2779 (3)	0.5368 (3)	0.3186 (2)	0.0454 (9)
H20	0.2872	0.5026	0.3650	0.054*
C21	0.3148 (3)	0.4731 (3)	0.26698 (18)	0.0373 (8)
C22	0.3132 (3)	0.2404 (3)	0.29312 (18)	0.0359 (8)
C23	0.1966 (3)	0.2469 (3)	0.2822 (2)	0.0454 (9)
H23	0.1576	0.3194	0.2634	0.054*
C24	0.1356 (3)	0.1487 (3)	0.2986 (2)	0.0494 (10)
H24	0.0568	0.1554	0.2901	0.059*
C25	0.1925 (3)	0.0417 (3)	0.32734 (19)	0.0444 (9)
C26	0.3081 (3)	0.0317 (3)	0.3370 (2)	0.0495 (10)
H26	0.3467	−0.0414	0.3552	0.059*
C27	0.3669 (3)	0.1297 (3)	0.3198 (2)	0.0466 (9)
H27	0.4451	0.1213	0.3262	0.056*
C28	0.0307 (3)	−0.0406 (4)	0.3561 (2)	0.0630 (11)
H28A	−0.0259	−0.0266	0.3081	0.076*
H28B	0.0320	0.0314	0.3868	0.076*
C29	−0.0001 (4)	−0.1531 (4)	0.3912 (2)	0.0735 (13)
H29A	0.0058	−0.2254	0.3624	0.088*
H29B	−0.0793	−0.1464	0.3910	0.088*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0619 (8)	0.1571 (14)	0.0604 (8)	−0.0277 (8)	0.0152 (6)	−0.0223 (8)
Cl2	0.1338 (15)	0.225 (2)	0.0792 (11)	−0.0733 (14)	−0.0024 (10)	0.0575 (12)
O1	0.067 (2)	0.102 (2)	0.0507 (18)	−0.0338 (18)	0.0035 (16)	−0.0008 (16)
O2	0.0647 (18)	0.0419 (15)	0.082 (2)	−0.0087 (13)	0.0374 (16)	0.0028 (13)
C1	0.128 (5)	0.091 (4)	0.085 (4)	−0.053 (3)	0.053 (4)	−0.026 (3)
C2	0.057 (3)	0.098 (4)	0.061 (3)	−0.029 (3)	0.019 (2)	−0.014 (2)
C3	0.046 (2)	0.057 (2)	0.046 (2)	−0.0065 (19)	0.008 (2)	−0.0004 (19)
C4	0.040 (2)	0.054 (2)	0.056 (2)	−0.0079 (18)	0.019 (2)	−0.0061 (19)
C5	0.041 (2)	0.045 (2)	0.040 (2)	−0.0015 (17)	0.0148 (18)	−0.0036 (16)
C6	0.041 (2)	0.0345 (18)	0.038 (2)	0.0000 (15)	0.0137 (17)	0.0001 (15)
C7	0.054 (3)	0.075 (3)	0.044 (2)	−0.019 (2)	0.017 (2)	0.003 (2)
C8	0.065 (3)	0.087 (3)	0.036 (2)	−0.018 (2)	0.011 (2)	0.004 (2)
C9	0.0362 (19)	0.0375 (18)	0.0336 (19)	0.0002 (15)	0.0121 (16)	0.0006 (15)
C10	0.038 (2)	0.0393 (19)	0.0350 (19)	−0.0052 (15)	0.0116 (16)	−0.0031 (15)
C11	0.057 (3)	0.045 (2)	0.055 (2)	−0.0002 (18)	0.026 (2)	−0.0043 (18)
C12	0.081 (3)	0.066 (3)	0.061 (3)	−0.002 (2)	0.038 (3)	−0.015 (2)
C13	0.094 (4)	0.086 (3)	0.043 (3)	−0.006 (3)	0.034 (3)	−0.010 (2)
C14	0.073 (3)	0.064 (3)	0.045 (2)	0.000 (2)	0.017 (2)	0.009 (2)
C15	0.042 (2)	0.049 (2)	0.036 (2)	−0.0062 (17)	0.0112 (17)	0.0002 (17)
C16	0.038 (2)	0.039 (2)	0.043 (2)	−0.0014 (16)	0.0068 (17)	0.0015 (16)
C17	0.057 (3)	0.047 (2)	0.060 (3)	0.0026 (19)	0.008 (2)	0.010 (2)
C18	0.055 (3)	0.043 (2)	0.086 (3)	0.0076 (19)	0.015 (2)	−0.001 (2)
C19	0.056 (3)	0.044 (2)	0.079 (3)	0.0018 (19)	0.027 (2)	−0.015 (2)
C20	0.044 (2)	0.046 (2)	0.048 (2)	−0.0053 (17)	0.0168 (18)	−0.0093 (17)
C21	0.0326 (19)	0.0363 (18)	0.042 (2)	−0.0032 (15)	0.0107 (16)	−0.0007 (16)
C22	0.036 (2)	0.0369 (19)	0.0349 (19)	−0.0020 (15)	0.0121 (16)	−0.0024 (15)
C23	0.042 (2)	0.040 (2)	0.052 (2)	−0.0007 (17)	0.0110 (18)	0.0040 (17)
C24	0.037 (2)	0.049 (2)	0.060 (2)	−0.0059 (17)	0.0121 (19)	0.0014 (19)
C25	0.049 (2)	0.037 (2)	0.050 (2)	−0.0071 (17)	0.0215 (19)	−0.0018 (17)
C26	0.053 (3)	0.039 (2)	0.060 (3)	0.0064 (18)	0.023 (2)	0.0060 (18)
C27	0.041 (2)	0.046 (2)	0.058 (2)	0.0055 (17)	0.0242 (19)	0.0028 (18)
C28	0.049 (3)	0.066 (3)	0.072 (3)	−0.015 (2)	0.017 (2)	0.008 (2)
C29	0.064 (3)	0.088 (3)	0.066 (3)	−0.025 (2)	0.017 (2)	0.010 (2)

Geometric parameters (Å, º) top

Cl1—C1	1.745 (6)	C13—C14	1.382 (6)
Cl2—C29	1.730 (5)	C13—H13	0.9300
O1—C3	1.371 (4)	C14—C15	1.382 (5)
O1—C2	1.385 (5)	C14—H14	0.9300
O2—C25	1.374 (4)	C15—C16	1.466 (5)
O2—C28	1.413 (5)	C16—C17	1.387 (5)
C1—C2	1.506 (6)	C16—C21	1.392 (4)
C1—H1A	0.9700	C17—C18	1.381 (6)
C1—H1B	0.9700	C17—H17	0.9300
C2—H2A	0.9700	C18—C19	1.365 (6)
C2—H2B	0.9700	C18—H18	0.9300
C3—C8	1.363 (5)	C19—C20	1.382 (5)
C3—C4	1.376 (5)	C19—H19	0.9300
C4—C5	1.388 (5)	C20—C21	1.386 (5)
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.372 (5)	C22—C23	1.377 (5)
C5—H5	0.9300	C22—C27	1.383 (5)
C6—C7	1.388 (5)	C23—C24	1.387 (5)
C6—C9	1.531 (5)	C23—H23	0.9300
C7—C8	1.368 (5)	C24—C25	1.373 (5)
C7—H7	0.9300	C24—H24	0.9300
C8—H8	0.9300	C25—C26	1.372 (5)
C9—C10	1.533 (4)	C26—C27	1.377 (5)
C9—C22	1.532 (4)	C26—H26	0.9300
C9—C21	1.541 (4)	C27—H27	0.9300
C10—C11	1.379 (5)	C28—C29	1.492 (5)
C10—C15	1.389 (5)	C28—H28A	0.9700
C11—C12	1.385 (5)	C28—H28B	0.9700
C11—H11	0.9300	C29—H29A	0.9700
C12—C13	1.370 (6)	C29—H29B	0.9700
C12—H12	0.9300

C3—O1—C2	118.6 (3)	C13—C14—H14	120.9
C25—O2—C28	117.5 (3)	C14—C15—C10	120.9 (3)
C2—C1—Cl1	114.8 (4)	C14—C15—C16	130.1 (3)
C2—C1—H1A	108.6	C10—C15—C16	109.0 (3)
Cl1—C1—H1A	108.6	C17—C16—C21	120.2 (3)
C2—C1—H1B	108.6	C17—C16—C15	131.3 (3)
Cl1—C1—H1B	108.6	C21—C16—C15	108.4 (3)
H1A—C1—H1B	107.5	C18—C17—C16	118.6 (4)
O1—C2—C1	107.5 (4)	C18—C17—H17	120.7
O1—C2—H2A	110.2	C16—C17—H17	120.7
C1—C2—H2A	110.2	C19—C18—C17	121.4 (4)
O1—C2—H2B	110.2	C19—C18—H18	119.3
C1—C2—H2B	110.2	C17—C18—H18	119.3
H2A—C2—H2B	108.5	C18—C19—C20	120.5 (4)
C8—C3—O1	115.7 (3)	C18—C19—H19	119.8
C8—C3—C4	119.3 (4)	C20—C19—H19	119.8
O1—C3—C4	124.9 (3)	C19—C20—C21	119.1 (4)
C3—C4—C5	119.2 (3)	C19—C20—H20	120.4
C3—C4—H4	120.4	C21—C20—H20	120.4
C5—C4—H4	120.4	C20—C21—C16	120.1 (3)
C6—C5—C4	122.0 (3)	C20—C21—C9	128.6 (3)
C6—C5—H5	119.0	C16—C21—C9	111.2 (3)
C4—C5—H5	119.0	C23—C22—C27	116.8 (3)
C5—C6—C7	117.3 (3)	C23—C22—C9	122.1 (3)
C5—C6—C9	122.3 (3)	C27—C22—C9	121.2 (3)
C7—C6—C9	119.9 (3)	C22—C23—C24	122.1 (3)
C8—C7—C6	121.0 (4)	C22—C23—H23	118.9
C8—C7—H7	119.5	C24—C23—H23	118.9
C6—C7—H7	119.5	C25—C24—C23	119.6 (3)
C3—C8—C7	121.0 (4)	C25—C24—H24	120.2
C3—C8—H8	119.5	C23—C24—H24	120.2
C7—C8—H8	119.5	C26—C25—O2	116.7 (3)
C10—C9—C6	113.0 (3)	C26—C25—C24	119.5 (3)
C10—C9—C22	111.1 (3)	O2—C25—C24	123.8 (3)
C6—C9—C22	112.5 (3)	C25—C26—C27	120.1 (3)
C10—C9—C21	100.2 (3)	C25—C26—H26	120.0
C6—C9—C21	106.3 (3)	C27—C26—H26	120.0
C22—C9—C21	113.1 (3)	C26—C27—C22	121.9 (3)
C11—C10—C15	120.3 (3)	C26—C27—H27	119.0
C11—C10—C9	128.5 (3)	C22—C27—H27	119.0
C15—C10—C9	111.2 (3)	O2—C28—C29	108.6 (3)
C12—C11—C10	118.4 (4)	O2—C28—H28A	110.0
C12—C11—H11	120.8	C29—C28—H28A	110.0
C10—C11—H11	120.8	O2—C28—H28B	110.0
C13—C12—C11	121.2 (4)	C29—C28—H28B	110.0
C13—C12—H12	119.4	H28A—C28—H28B	108.4
C11—C12—H12	119.4	C28—C29—Cl2	111.8 (3)
C12—C13—C14	120.8 (4)	C28—C29—H29A	109.3
C12—C13—H13	119.6	Cl2—C29—H29A	109.3
C14—C13—H13	119.6	C28—C29—H29B	109.3
C15—C14—C13	118.3 (4)	Cl2—C29—H29B	109.3
C15—C14—H14	120.9	H29A—C29—H29B	107.9

C3—O1—C2—C1	166.2 (4)	C14—C15—C16—C21	178.5 (4)
Cl1—C1—C2—O1	61.3 (5)	C10—C15—C16—C21	−1.7 (4)
C2—O1—C3—C8	−163.0 (4)	C21—C16—C17—C18	−1.3 (5)
C2—O1—C3—C4	14.7 (6)	C15—C16—C17—C18	−178.0 (4)
C8—C3—C4—C5	4.1 (6)	C16—C17—C18—C19	−0.3 (6)
O1—C3—C4—C5	−173.6 (4)	C17—C18—C19—C20	0.9 (6)
C3—C4—C5—C6	−0.2 (5)	C18—C19—C20—C21	0.0 (6)
C4—C5—C6—C7	−3.1 (5)	C19—C20—C21—C16	−1.6 (5)
C4—C5—C6—C9	168.4 (3)	C19—C20—C21—C9	175.2 (3)
C5—C6—C7—C8	2.7 (6)	C17—C16—C21—C20	2.2 (5)
C9—C6—C7—C8	−169.1 (4)	C15—C16—C21—C20	179.6 (3)
O1—C3—C8—C7	173.3 (4)	C17—C16—C21—C9	−175.1 (3)
C4—C3—C8—C7	−4.6 (7)	C15—C16—C21—C9	2.3 (4)
C6—C7—C8—C3	1.1 (7)	C10—C9—C21—C20	−179.0 (3)
C5—C6—C9—C10	21.6 (4)	C6—C9—C21—C20	−61.2 (4)
C7—C6—C9—C10	−167.0 (3)	C22—C9—C21—C20	62.8 (4)
C5—C6—C9—C22	148.4 (3)	C10—C9—C21—C16	−2.0 (3)
C7—C6—C9—C22	−40.2 (4)	C6—C9—C21—C16	115.8 (3)
C5—C6—C9—C21	−87.3 (4)	C22—C9—C21—C16	−120.3 (3)
C7—C6—C9—C21	84.1 (4)	C10—C9—C22—C23	−96.1 (4)
C6—C9—C10—C11	66.9 (4)	C6—C9—C22—C23	136.1 (3)
C22—C9—C10—C11	−60.6 (4)	C21—C9—C22—C23	15.6 (4)
C21—C9—C10—C11	179.6 (3)	C10—C9—C22—C27	83.4 (4)
C6—C9—C10—C15	−111.7 (3)	C6—C9—C22—C27	−44.4 (4)
C22—C9—C10—C15	120.7 (3)	C21—C9—C22—C27	−164.9 (3)
C21—C9—C10—C15	0.9 (3)	C27—C22—C23—C24	1.4 (5)
C15—C10—C11—C12	−1.7 (5)	C9—C22—C23—C24	−179.1 (3)
C9—C10—C11—C12	179.8 (3)	C22—C23—C24—C25	0.8 (6)
C10—C11—C12—C13	0.9 (6)	C28—O2—C25—C26	164.5 (3)
C11—C12—C13—C14	0.2 (7)	C28—O2—C25—C24	−15.4 (5)
C12—C13—C14—C15	−0.5 (7)	C23—C24—C25—C26	−2.4 (5)
C13—C14—C15—C10	−0.3 (6)	C23—C24—C25—O2	177.5 (3)
C13—C14—C15—C16	179.5 (4)	O2—C25—C26—C27	−178.1 (3)
C11—C10—C15—C14	1.4 (5)	C24—C25—C26—C27	1.8 (6)
C9—C10—C15—C14	−179.8 (3)	C25—C26—C27—C22	0.5 (6)
C11—C10—C15—C16	−178.4 (3)	C23—C22—C27—C26	−2.1 (5)
C9—C10—C15—C16	0.4 (4)	C9—C22—C27—C26	178.4 (3)
C14—C15—C16—C17	−4.5 (6)	C25—O2—C28—C29	−169.9 (3)
C10—C15—C16—C17	175.3 (4)	O2—C28—C29—Cl2	66.6 (4)

Experimental details

Crystal data
Chemical formula	C₂₉H₂₄Cl₂O₂
M_r	475.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	12.2334 (7), 10.8063 (6), 19.0374 (12)
β (°)	108.172 (2)
V (Å³)	2391.2 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.27 × 0.15 × 0.07

Data collection
Diffractometer	Bruker Kappa APEXII
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.783, 0.862
No. of measured, independent and observed [I > 2σ(I)] reflections	18388, 4206, 2326
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.177, 1.01
No. of reflections	4206
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.66

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

We thank the Higher Education Commission of Pakistan, GC University and the University of Malaya for supporting this study.

References

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