(8S,9R,10S,11S,13S,14S,16S,17R)-4,4-Dichloro-16β-methyl-3,20-dioxo-17,21-bis­(propano­yloxy)-5β,8β-epoxy­pregna-1,9-diene

Ketuly, K.A.; Hadi, A.H.A.; Ng, S.W.

doi:10.1107/S1600536809028293

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2220

doi:10.1107/S1600536809028293

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(8S,9R,10S,11S,13S,14S,16S,17R)-4,4-Dichloro-16β-methyl-3,20-dioxo-17,21-bis(propanoyloxy)-5β,8β-epoxypregna-1,9-diene

Kamal Aziz Ketuly,^a A. Hamid A. Hadi ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 16 July 2009; accepted 17 July 2009; online 22 July 2009)

The title compound, C₂₈H₃₄Cl₂O₇, is a derivative of the glucocorticoid steroid beclomethasone dipropionate. It features an expoxide linkage [angle at oxygen = 96.6 (2)°]. The dichlorocyclohexenone ring adopts an envelope conformation, with the C atom bearing the two Cl substituents representing the flap. The dichloromethyl C atom deviates by 0.471 (4) Å from the plane defined by the other five atoms, whose maximum r.m.s. deviation is 0.04 Å.

Related literature

For related structures, see: Ketuly et al. (2009a ,b ).

Experimental

Crystal data

C₂₈H₃₄Cl₂O₇
M_r = 553.45
Orthorhombic, P 2₁ 2₁ 2₁
a = 11.1556 (2) Å
b = 12.2281 (2) Å
c = 19.3476 (4) Å
V = 2639.24 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 140 K
0.30 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.918, T_max = 0.971
24071 measured reflections
6067 independent reflections
4878 reflections with I > 2σ(I)
R_int = 0.083

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.116
S = 1.03
6067 reflections
339 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.29 e Å⁻³
Absolute structure: Flack (1983 ), 3199 Friedel pairs
Flack parameter: −0.16 (6)

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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809028293/bt5010sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809028293/bt5010Isup2.hkl

checkCIF report

Related literature top

For related structures, see: Ketuly et al. (2009a,b).

Experimental top

The synthesis of the compound is described in a 1988 study commissioned by the Glaxo company (now called Glaxo Smith Kline), External Report No. WAP/88/007. Crystals were grown from its solution in ethyl acetate; m.p. 492–493 K. C7H elemental analysis. Calc. for C₂₈H₃₄Cl₂O₇(MW 552): C 60.87, H, 6.15, Cl 14.26%. Found C 61.36, H 6.33, Cl 14.26 %.

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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C₂₈H₃₄Cl₂O₇ at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

(8S,9R,10S,11S,13S,14S,16S, 17R)-4,4-Dichloro-16β-methyl-3,20-dioxo-17,21-bis(propanoyloxy)- 5β,8β-epoxypregna-1,9-diene top

Crystal data top

C₂₈H₃₄Cl₂O₇	F(000) = 1168
M_r = 553.45	D_x = 1.393 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6462 reflections
a = 11.1556 (2) Å	θ = 2.5–28.0°
b = 12.2281 (2) Å	µ = 0.29 mm⁻¹
c = 19.3476 (4) Å	T = 140 K
V = 2639.24 (8) Å³	Multiple crystalline block, colorless
Z = 4	0.30 × 0.15 × 0.10 mm

Data collection top

Bruker SMART APEX diffractometer	6067 independent reflections
Radiation source: fine-focus sealed tube	4878 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.083
ω scans	θ_max = 27.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.918, T_max = 0.971	k = −15→15
24071 measured reflections	l = −24→25

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.116	w = 1/[σ²(F_o²) + (0.0588P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
6067 reflections	Δρ_max = 0.45 e Å⁻³
339 parameters	Δρ_min = −0.29 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 3199 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.16 (6)

Crystal data top

C₂₈H₃₄Cl₂O₇	V = 2639.24 (8) Å³
M_r = 553.45	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 11.1556 (2) Å	µ = 0.29 mm⁻¹
b = 12.2281 (2) Å	T = 140 K
c = 19.3476 (4) Å	0.30 × 0.15 × 0.10 mm

Data collection top

Bruker SMART APEX diffractometer	6067 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4878 reflections with I > 2σ(I)
T_min = 0.918, T_max = 0.971	R_int = 0.083
24071 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.116	Δρ_max = 0.45 e Å⁻³
S = 1.03	Δρ_min = −0.29 e Å⁻³
6067 reflections	Absolute structure: Flack (1983), 3199 Friedel pairs
339 parameters	Absolute structure parameter: −0.16 (6)
0 restraints

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

	x	y	z	U_iso*/U_eq
Cl1	0.59256 (6)	0.63874 (6)	0.83223 (4)	0.03035 (17)
Cl2	0.40010 (7)	0.78271 (6)	0.78724 (3)	0.02583 (16)
O1	0.5154 (2)	0.76634 (19)	0.94879 (11)	0.0395 (6)
O2	0.39813 (17)	0.49261 (14)	0.87881 (9)	0.0186 (4)
O3	0.23417 (17)	0.17101 (16)	1.02004 (9)	0.0207 (4)
O4	0.30538 (19)	0.00381 (17)	1.04842 (10)	0.0270 (5)
O5	0.1490 (2)	−0.00893 (18)	0.88479 (11)	0.0311 (5)
O6	−0.04283 (18)	−0.03711 (18)	0.96500 (10)	0.0289 (5)
O7	−0.1240 (2)	0.0925 (2)	0.89835 (13)	0.0441 (6)
C1	0.4397 (2)	0.6766 (2)	0.84723 (14)	0.0217 (6)
C2	0.4287 (3)	0.7295 (2)	0.91964 (14)	0.0247 (6)
C3	0.3070 (3)	0.7333 (2)	0.94717 (14)	0.0276 (6)
H3	0.2913	0.7807	0.9850	0.033*
C4	0.2167 (3)	0.6739 (2)	0.92216 (14)	0.0245 (6)
H4	0.1416	0.6801	0.9450	0.029*
C5	0.2229 (2)	0.5983 (2)	0.86127 (14)	0.0203 (6)
C6	0.1319 (3)	0.6378 (3)	0.80715 (15)	0.0280 (7)
H6A	0.0528	0.6448	0.8287	0.042*
H6B	0.1278	0.5849	0.7692	0.042*
H6C	0.1572	0.7091	0.7891	0.042*
C7	0.3561 (2)	0.5809 (2)	0.83546 (14)	0.0190 (5)
C8	0.3576 (3)	0.5283 (2)	0.76388 (14)	0.0233 (6)
H8A	0.4396	0.5260	0.7443	0.028*
H8B	0.3037	0.5670	0.7314	0.028*
C9	0.3107 (3)	0.4125 (2)	0.78109 (14)	0.0244 (6)
H9A	0.2310	0.3996	0.7601	0.029*
H9B	0.3671	0.3555	0.7648	0.029*
C10	0.3032 (2)	0.4144 (2)	0.86073 (13)	0.0184 (5)
C11	0.1961 (2)	0.4800 (2)	0.88369 (13)	0.0186 (5)
C12	0.1084 (3)	0.4403 (2)	0.92204 (14)	0.0227 (6)
H12	0.0462	0.4885	0.9361	0.027*
C13	0.1017 (3)	0.3215 (2)	0.94484 (14)	0.0233 (6)
H13A	0.0202	0.2931	0.9356	0.028*
H13B	0.1160	0.3173	0.9953	0.028*
C14	0.1939 (3)	0.2494 (2)	0.90729 (13)	0.0209 (6)
C15	0.1423 (3)	0.2191 (3)	0.83575 (15)	0.0272 (6)
H15A	0.1188	0.2858	0.8112	0.041*
H15B	0.0720	0.1720	0.8418	0.041*
H15C	0.2033	0.1801	0.8089	0.041*
C16	0.3147 (2)	0.3108 (2)	0.90233 (13)	0.0188 (6)
H16	0.3370	0.3329	0.9504	0.023*
C17	0.4044 (3)	0.2242 (2)	0.87993 (14)	0.0234 (6)
H17A	0.4875	0.2476	0.8900	0.028*
H17B	0.3971	0.2086	0.8299	0.028*
C18	0.3695 (2)	0.1232 (2)	0.92347 (15)	0.0229 (6)
H18	0.4193	0.1264	0.9664	0.027*
C19	0.4019 (3)	0.0166 (2)	0.88754 (17)	0.0334 (7)
H19A	0.3769	−0.0452	0.9164	0.050*
H19B	0.4888	0.0135	0.8803	0.050*
H19C	0.3609	0.0128	0.8428	0.050*
C20	0.2361 (2)	0.1420 (2)	0.94671 (13)	0.0203 (6)
C21	0.2739 (2)	0.0941 (2)	1.06562 (14)	0.0223 (6)
C22	0.2662 (3)	0.1371 (3)	1.13866 (14)	0.0309 (7)
H22A	0.1811	0.1396	1.1530	0.037*
H22B	0.2979	0.2127	1.1399	0.037*
C23	0.3360 (3)	0.0672 (3)	1.18969 (15)	0.0304 (7)
H23A	0.3259	0.0967	1.2364	0.046*
H23B	0.4212	0.0678	1.1773	0.046*
H23C	0.3058	−0.0081	1.1882	0.046*
C24	0.1462 (2)	0.0488 (2)	0.93501 (14)	0.0214 (6)
C25	0.0457 (3)	0.0390 (3)	0.98795 (15)	0.0300 (7)
H25A	0.0792	0.0143	1.0327	0.036*
H25B	0.0082	0.1115	0.9951	0.036*
C26	−0.1214 (3)	0.0001 (3)	0.91806 (15)	0.0277 (7)
C27	−0.2012 (3)	−0.0907 (3)	0.89423 (15)	0.0295 (7)
H27A	−0.2541	−0.0633	0.8570	0.035*
H27B	−0.2526	−0.1145	0.9331	0.035*
C28	−0.1304 (3)	−0.1883 (3)	0.86761 (19)	0.0401 (8)
H28A	−0.1857	−0.2425	0.8482	0.060*
H28B	−0.0853	−0.2212	0.9058	0.060*
H28C	−0.0745	−0.1640	0.8316	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0214 (3)	0.0217 (4)	0.0479 (4)	−0.0017 (3)	0.0023 (3)	0.0073 (3)
Cl2	0.0363 (4)	0.0168 (3)	0.0244 (3)	−0.0009 (3)	−0.0006 (3)	0.0060 (3)
O1	0.0536 (14)	0.0287 (14)	0.0360 (11)	−0.0118 (11)	−0.0154 (11)	0.0019 (10)
O2	0.0217 (9)	0.0123 (9)	0.0219 (9)	−0.0012 (8)	0.0006 (8)	0.0013 (7)
O3	0.0273 (10)	0.0186 (10)	0.0162 (9)	−0.0005 (8)	0.0001 (7)	−0.0002 (7)
O4	0.0384 (11)	0.0173 (11)	0.0253 (10)	0.0010 (9)	0.0021 (9)	0.0009 (8)
O5	0.0447 (12)	0.0225 (12)	0.0260 (11)	−0.0040 (10)	0.0010 (9)	−0.0058 (9)
O6	0.0312 (11)	0.0301 (13)	0.0253 (10)	−0.0109 (9)	−0.0033 (9)	0.0064 (9)
O7	0.0477 (15)	0.0265 (13)	0.0581 (16)	0.0041 (11)	−0.0032 (11)	0.0130 (11)
C1	0.0258 (14)	0.0157 (14)	0.0234 (14)	0.0028 (11)	−0.0012 (11)	0.0039 (11)
C2	0.0393 (18)	0.0135 (14)	0.0214 (13)	−0.0032 (13)	−0.0081 (12)	0.0036 (11)
C3	0.0491 (18)	0.0150 (15)	0.0185 (13)	0.0053 (13)	0.0004 (13)	−0.0009 (11)
C4	0.0325 (15)	0.0195 (15)	0.0215 (13)	0.0060 (13)	0.0046 (12)	0.0033 (11)
C5	0.0200 (13)	0.0175 (15)	0.0234 (13)	−0.0016 (11)	0.0042 (11)	0.0027 (11)
C6	0.0304 (15)	0.0232 (16)	0.0305 (16)	0.0000 (13)	−0.0024 (12)	0.0066 (12)
C7	0.0224 (12)	0.0157 (14)	0.0188 (13)	0.0017 (11)	−0.0008 (10)	0.0008 (11)
C8	0.0315 (14)	0.0196 (15)	0.0188 (14)	0.0028 (12)	0.0041 (11)	0.0006 (11)
C9	0.0338 (15)	0.0176 (14)	0.0219 (14)	−0.0020 (12)	0.0002 (12)	0.0004 (12)
C10	0.0202 (13)	0.0153 (14)	0.0197 (12)	−0.0042 (11)	−0.0003 (10)	−0.0003 (10)
C11	0.0241 (13)	0.0131 (13)	0.0188 (13)	0.0007 (11)	−0.0041 (10)	−0.0002 (10)
C12	0.0233 (14)	0.0201 (14)	0.0247 (14)	0.0052 (12)	0.0002 (11)	−0.0004 (11)
C13	0.0218 (13)	0.0218 (15)	0.0262 (14)	−0.0003 (12)	0.0030 (12)	0.0018 (11)
C14	0.0248 (13)	0.0165 (15)	0.0213 (13)	−0.0029 (11)	0.0010 (11)	0.0013 (10)
C15	0.0338 (15)	0.0212 (15)	0.0267 (14)	−0.0063 (13)	−0.0049 (12)	0.0042 (12)
C16	0.0211 (12)	0.0167 (14)	0.0187 (13)	0.0004 (11)	0.0024 (10)	−0.0033 (10)
C17	0.0275 (13)	0.0155 (13)	0.0271 (13)	0.0013 (13)	0.0052 (12)	0.0017 (11)
C18	0.0272 (14)	0.0200 (15)	0.0214 (13)	0.0007 (12)	0.0023 (11)	0.0002 (11)
C19	0.0389 (16)	0.0170 (15)	0.0442 (18)	0.0054 (14)	0.0131 (15)	−0.0002 (13)
C20	0.0239 (13)	0.0189 (14)	0.0180 (12)	−0.0006 (11)	−0.0003 (10)	−0.0019 (11)
C21	0.0219 (13)	0.0233 (16)	0.0217 (13)	−0.0040 (12)	−0.0013 (10)	0.0007 (11)
C22	0.0422 (18)	0.0297 (18)	0.0209 (14)	0.0024 (15)	0.0012 (12)	−0.0021 (12)
C23	0.0331 (16)	0.0353 (19)	0.0228 (15)	−0.0038 (14)	−0.0012 (12)	0.0011 (13)
C24	0.0269 (14)	0.0166 (14)	0.0208 (14)	−0.0024 (12)	−0.0003 (11)	0.0014 (11)
C25	0.0292 (15)	0.0348 (19)	0.0259 (15)	−0.0137 (14)	0.0019 (12)	−0.0008 (13)
C26	0.0304 (16)	0.0291 (17)	0.0238 (14)	0.0015 (13)	0.0033 (12)	0.0048 (12)
C27	0.0272 (15)	0.0389 (19)	0.0224 (14)	−0.0047 (14)	−0.0033 (12)	0.0041 (13)
C28	0.046 (2)	0.0324 (19)	0.0417 (19)	−0.0022 (15)	−0.0091 (15)	−0.0061 (15)

Geometric parameters (Å, º) top

Cl1—C1	1.791 (3)	C13—H13A	0.9900
Cl2—C1	1.796 (3)	C13—H13B	0.9900
O1—C2	1.207 (3)	C14—C15	1.545 (4)
O2—C7	1.445 (3)	C14—C16	1.546 (4)
O2—C10	1.470 (3)	C14—C20	1.590 (4)
O3—C21	1.364 (3)	C15—H15A	0.9800
O3—C20	1.463 (3)	C15—H15B	0.9800
O4—C21	1.205 (4)	C15—H15C	0.9800
O5—C24	1.201 (3)	C16—C17	1.520 (4)
O6—C26	1.341 (3)	C16—H16	1.0000
O6—C25	1.428 (4)	C17—C18	1.545 (4)
O7—C26	1.193 (4)	C17—H17A	0.9900
C1—C7	1.514 (4)	C17—H17B	0.9900
C1—C2	1.548 (4)	C18—C19	1.521 (4)
C2—C3	1.458 (4)	C18—C20	1.572 (4)
C3—C4	1.332 (4)	C18—H18	1.0000
C3—H3	0.9500	C19—H19A	0.9800
C4—C5	1.500 (4)	C19—H19B	0.9800
C4—H4	0.9500	C19—H19C	0.9800
C5—C6	1.536 (4)	C20—C24	1.535 (4)
C5—C11	1.539 (4)	C21—C22	1.510 (4)
C5—C7	1.583 (4)	C22—C23	1.520 (4)
C6—H6A	0.9800	C22—H22A	0.9900
C6—H6B	0.9800	C22—H22B	0.9900
C6—H6C	0.9800	C23—H23A	0.9800
C7—C8	1.527 (4)	C23—H23B	0.9800
C8—C9	1.546 (4)	C23—H23C	0.9800
C8—H8A	0.9900	C24—C25	1.523 (4)
C8—H8B	0.9900	C25—H25A	0.9900
C9—C10	1.543 (4)	C25—H25B	0.9900
C9—H9A	0.9900	C26—C27	1.496 (4)
C9—H9B	0.9900	C27—C28	1.521 (5)
C10—C11	1.505 (4)	C27—H27A	0.9900
C10—C16	1.506 (4)	C27—H27B	0.9900
C11—C12	1.321 (4)	C28—H28A	0.9800
C12—C13	1.519 (4)	C28—H28B	0.9800
C12—H12	0.9500	C28—H28C	0.9800
C13—C14	1.538 (4)

C7—O2—C10	96.57 (18)	H15A—C15—H15B	109.5
C21—O3—C20	117.1 (2)	C14—C15—H15C	109.5
C26—O6—C25	116.2 (3)	H15A—C15—H15C	109.5
C7—C1—C2	114.2 (2)	H15B—C15—H15C	109.5
C7—C1—Cl1	111.2 (2)	C10—C16—C17	119.3 (2)
C2—C1—Cl1	109.30 (19)	C10—C16—C14	111.5 (2)
C7—C1—Cl2	108.06 (19)	C17—C16—C14	104.7 (2)
C2—C1—Cl2	105.28 (19)	C10—C16—H16	106.9
Cl1—C1—Cl2	108.43 (15)	C17—C16—H16	106.9
O1—C2—C3	124.3 (3)	C14—C16—H16	106.9
O1—C2—C1	121.0 (3)	C16—C17—C18	103.7 (2)
C3—C2—C1	114.7 (2)	C16—C17—H17A	111.0
C4—C3—C2	123.6 (3)	C18—C17—H17A	111.0
C4—C3—H3	118.2	C16—C17—H17B	111.0
C2—C3—H3	118.2	C18—C17—H17B	111.0
C3—C4—C5	125.9 (3)	H17A—C17—H17B	109.0
C3—C4—H4	117.0	C19—C18—C17	112.1 (2)
C5—C4—H4	117.0	C19—C18—C20	118.7 (3)
C4—C5—C6	108.1 (2)	C17—C18—C20	106.1 (2)
C4—C5—C11	110.5 (2)	C19—C18—H18	106.4
C6—C5—C11	111.1 (2)	C17—C18—H18	106.4
C4—C5—C7	111.9 (2)	C20—C18—H18	106.4
C6—C5—C7	116.6 (2)	C18—C19—H19A	109.5
C11—C5—C7	98.3 (2)	C18—C19—H19B	109.5
C5—C6—H6A	109.5	H19A—C19—H19B	109.5
C5—C6—H6B	109.5	C18—C19—H19C	109.5
H6A—C6—H6B	109.5	H19A—C19—H19C	109.5
C5—C6—H6C	109.5	H19B—C19—H19C	109.5
H6A—C6—H6C	109.5	O3—C20—C24	108.3 (2)
H6B—C6—H6C	109.5	O3—C20—C18	109.1 (2)
O2—C7—C1	106.9 (2)	C24—C20—C18	117.9 (2)
O2—C7—C8	102.0 (2)	O3—C20—C14	105.1 (2)
C1—C7—C8	117.1 (2)	C24—C20—C14	110.5 (2)
O2—C7—C5	102.8 (2)	C18—C20—C14	105.3 (2)
C1—C7—C5	115.3 (2)	O4—C21—O3	123.2 (2)
C8—C7—C5	110.7 (2)	O4—C21—C22	126.4 (3)
C7—C8—C9	100.7 (2)	O3—C21—C22	110.3 (2)
C7—C8—H8A	111.6	C21—C22—C23	112.5 (3)
C9—C8—H8A	111.6	C21—C22—H22A	109.1
C7—C8—H8B	111.6	C23—C22—H22A	109.1
C9—C8—H8B	111.6	C21—C22—H22B	109.1
H8A—C8—H8B	109.4	C23—C22—H22B	109.1
C10—C9—C8	102.7 (2)	H22A—C22—H22B	107.8
C10—C9—H9A	111.2	C22—C23—H23A	109.5
C8—C9—H9A	111.2	C22—C23—H23B	109.5
C10—C9—H9B	111.2	H23A—C23—H23B	109.5
C8—C9—H9B	111.2	C22—C23—H23C	109.5
H9A—C9—H9B	109.1	H23A—C23—H23C	109.5
O2—C10—C11	98.9 (2)	H23B—C23—H23C	109.5
O2—C10—C16	111.0 (2)	O5—C24—C25	121.1 (3)
C11—C10—C16	111.0 (2)	O5—C24—C20	122.6 (3)
O2—C10—C9	102.0 (2)	C25—C24—C20	116.1 (2)
C11—C10—C9	110.2 (2)	O6—C25—C24	110.6 (2)
C16—C10—C9	121.1 (2)	O6—C25—H25A	109.5
C12—C11—C10	123.9 (3)	C24—C25—H25A	109.5
C12—C11—C5	130.3 (3)	O6—C25—H25B	109.5
C10—C11—C5	105.3 (2)	C24—C25—H25B	109.5
C11—C12—C13	123.4 (3)	H25A—C25—H25B	108.1
C11—C12—H12	118.3	O7—C26—O6	123.6 (3)
C13—C12—H12	118.3	O7—C26—C27	126.2 (3)
C12—C13—C14	112.3 (2)	O6—C26—C27	110.2 (3)
C12—C13—H13A	109.2	C26—C27—C28	112.2 (3)
C14—C13—H13A	109.2	C26—C27—H27A	109.2
C12—C13—H13B	109.2	C28—C27—H27A	109.2
C14—C13—H13B	109.2	C26—C27—H27B	109.2
H13A—C13—H13B	107.9	C28—C27—H27B	109.2
C13—C14—C15	108.2 (2)	H27A—C27—H27B	107.9
C13—C14—C16	109.5 (2)	C27—C28—H28A	109.5
C15—C14—C16	112.7 (2)	C27—C28—H28B	109.5
C13—C14—C20	116.4 (2)	H28A—C28—H28B	109.5
C15—C14—C20	110.0 (2)	C27—C28—H28C	109.5
C16—C14—C20	100.0 (2)	H28A—C28—H28C	109.5
C14—C15—H15A	109.5	H28B—C28—H28C	109.5
C14—C15—H15B	109.5

C7—C1—C2—O1	145.1 (3)	C5—C11—C12—C13	−174.1 (3)
Cl1—C1—C2—O1	19.8 (3)	C11—C12—C13—C14	−10.9 (4)
Cl2—C1—C2—O1	−96.5 (3)	C12—C13—C14—C15	−81.5 (3)
C7—C1—C2—C3	−36.6 (3)	C12—C13—C14—C16	41.7 (3)
Cl1—C1—C2—C3	−162.0 (2)	C12—C13—C14—C20	154.1 (2)
Cl2—C1—C2—C3	81.7 (3)	O2—C10—C16—C17	−80.9 (3)
O1—C2—C3—C4	−165.8 (3)	C11—C10—C16—C17	170.1 (2)
C1—C2—C3—C4	16.0 (4)	C9—C10—C16—C17	38.5 (4)
C2—C3—C4—C5	−2.5 (5)	O2—C10—C16—C14	156.8 (2)
C3—C4—C5—C6	−120.7 (3)	C11—C10—C16—C14	47.9 (3)
C3—C4—C5—C11	117.5 (3)	C9—C10—C16—C14	−83.7 (3)
C3—C4—C5—C7	9.1 (4)	C13—C14—C16—C10	−62.1 (3)
C10—O2—C7—C1	177.9 (2)	C15—C14—C16—C10	58.3 (3)
C10—O2—C7—C8	−58.6 (2)	C20—C14—C16—C10	175.1 (2)
C10—O2—C7—C5	56.1 (2)	C13—C14—C16—C17	167.5 (2)
C2—C1—C7—O2	−69.4 (3)	C15—C14—C16—C17	−72.0 (3)
Cl1—C1—C7—O2	54.9 (2)	C20—C14—C16—C17	44.7 (2)
Cl2—C1—C7—O2	173.80 (16)	C10—C16—C17—C18	−167.4 (2)
C2—C1—C7—C8	177.0 (2)	C14—C16—C17—C18	−41.8 (3)
Cl1—C1—C7—C8	−58.7 (3)	C16—C17—C18—C19	152.0 (2)
Cl2—C1—C7—C8	60.2 (3)	C16—C17—C18—C20	20.9 (3)
C2—C1—C7—C5	44.1 (3)	C21—O3—C20—C24	65.7 (3)
Cl1—C1—C7—C5	168.45 (18)	C21—O3—C20—C18	−63.7 (3)
Cl2—C1—C7—C5	−72.6 (2)	C21—O3—C20—C14	−176.2 (2)
C4—C5—C7—O2	86.0 (3)	C19—C18—C20—O3	126.9 (3)
C6—C5—C7—O2	−148.8 (2)	C17—C18—C20—O3	−105.9 (2)
C11—C5—C7—O2	−30.1 (2)	C19—C18—C20—C24	3.0 (4)
C4—C5—C7—C1	−29.9 (3)	C17—C18—C20—C24	130.2 (3)
C6—C5—C7—C1	95.3 (3)	C19—C18—C20—C14	−120.7 (3)
C11—C5—C7—C1	−146.0 (2)	C17—C18—C20—C14	6.5 (3)
C4—C5—C7—C8	−165.7 (2)	C13—C14—C20—O3	−33.2 (3)
C6—C5—C7—C8	−40.5 (3)	C15—C14—C20—O3	−156.7 (2)
C11—C5—C7—C8	78.2 (2)	C16—C14—C20—O3	84.6 (2)
O2—C7—C8—C9	39.8 (2)	C13—C14—C20—C24	83.4 (3)
C1—C7—C8—C9	156.1 (2)	C15—C14—C20—C24	−40.1 (3)
C5—C7—C8—C9	−69.1 (3)	C16—C14—C20—C24	−158.8 (2)
C7—C8—C9—C10	−5.8 (3)	C13—C14—C20—C18	−148.3 (2)
C7—O2—C10—C11	−59.3 (2)	C15—C14—C20—C18	88.2 (3)
C7—O2—C10—C16	−175.9 (2)	C16—C14—C20—C18	−30.6 (2)
C7—O2—C10—C9	53.8 (2)	C20—O3—C21—O4	−2.9 (4)
C8—C9—C10—O2	−29.0 (3)	C20—O3—C21—C22	179.8 (2)
C8—C9—C10—C11	75.3 (3)	O4—C21—C22—C23	16.6 (4)
C8—C9—C10—C16	−152.8 (2)	O3—C21—C22—C23	−166.2 (2)
O2—C10—C11—C12	−132.5 (3)	O3—C20—C24—O5	−161.5 (3)
C16—C10—C11—C12	−15.8 (4)	C18—C20—C24—O5	−37.1 (4)
C9—C10—C11—C12	121.2 (3)	C14—C20—C24—O5	83.9 (3)
O2—C10—C11—C5	40.5 (2)	O3—C20—C24—C25	23.5 (3)
C16—C10—C11—C5	157.1 (2)	C18—C20—C24—C25	147.9 (3)
C9—C10—C11—C5	−65.9 (3)	C14—C20—C24—C25	−91.1 (3)
C4—C5—C11—C12	48.3 (4)	C26—O6—C25—C24	−79.3 (3)
C6—C5—C11—C12	−71.6 (4)	O5—C24—C25—O6	−5.4 (4)
C7—C5—C11—C12	165.6 (3)	C20—C24—C25—O6	169.7 (2)
C4—C5—C11—C10	−124.0 (2)	C25—O6—C26—O7	−4.1 (4)
C6—C5—C11—C10	116.1 (2)	C25—O6—C26—C27	174.9 (2)
C7—C5—C11—C10	−6.7 (2)	O7—C26—C27—C28	124.6 (4)
C10—C11—C12—C13	−3.1 (4)	O6—C26—C27—C28	−54.3 (3)

Experimental details

Crystal data
Chemical formula	C₂₈H₃₄Cl₂O₇
M_r	553.45
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	140
a, b, c (Å)	11.1556 (2), 12.2281 (2), 19.3476 (4)
V (Å³)	2639.24 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.30 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.918, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	24071, 6067, 4878
R_int	0.083
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.116, 1.03
No. of reflections	6067
No. of parameters	339
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.29
Absolute structure	Flack (1983), 3199 Friedel pairs
Absolute structure parameter	−0.16 (6)

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

Acknowledgements

We thank the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Ketuly, K. A. A., Hadi, A. H. & Ng, S. W. (2009a). Acta Cryst. E65, o1821. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar

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