organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

2-Bromo­beclometasone dipropionate

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

(Received 24 June 2009; accepted 4 July 2009; online 11 July 2009)

In the crystal structure of 2-bromo­beclometasone dipropionate [systematic name: (8S,9R,10S,11S,13S,14S,16S,17R)-2-bromo-9α-chloro-11-hydr­oxy-10,13,16-trimethyl-3-oxo-17-[2-(propion­yloxy)acet­yl]-6,7,8,9,10,11,12,13,14,15,16,17-dodeca­hydro-3H-cyclo­penta­[a]phenanthren-17-yl propionate], C28H36BrClO7, the six-membered ring with the 1,4-diene-3-one composition is planar (r.m.s. deviations = 0.03 and 0.04 Å for the two independent mol­ecules), whereas the remaining six-membered rings have chair conformations. Each of the independent mol­ecules self-associates via O—H⋯Opropionate hydrogen bonding, generating a supra­molecular chain running along the b axis. The crystal is twinned, with the monoclinic unit cell emulating an orthorhomic crystal system; the major twin component constitutes approximately 60%.

Related literature

For the NMR and crystal structure of the asthma drug beclometasone dipropionate monohydrate, see: Othman et al. (2008[Othman, A., Harris, R. K., Hodgkinson, P., Christopher, E. A. & Lancaster, R. W. (2008). New J. Chem. 32, 1796-1806.]); Duax et al. (1981[Duax, W. L., Cody, V. & Strong, P. D. (1981). Acta Cryst. B37, 383-387.]).

[Scheme 1]

Experimental

Crystal data
  • C28H36BrClO7

  • Mr = 599.93

  • Monoclinic, P 21

  • a = 12.0999 (3) Å

  • b = 13.8673 (3) Å

  • c = 16.7971 (4) Å

  • β = 90.106 (1)°

  • V = 2818.4 (1) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.60 mm−1

  • T = 140 K

  • 0.22 × 0.11 × 0.02 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.642, Tmax = 0.746 (expected range = 0.834–0.969)

  • 23151 measured reflections

  • 12754 independent reflections

  • 9841 reflections with I > 2σ(I)

  • Rint = 0.045

Refinement
  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.086

  • S = 0.94

  • 12754 reflections

  • 680 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.61 e Å−3

  • Δρmin = −0.52 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 6028 Friedel pairs

  • Flack parameter: 0.001 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2⋯O7i 0.82 2.11 2.817 (5) 145
O9—H9⋯O14ii 0.82 1.98 2.754 (5) 158
Symmetry codes: (i) [-x, y+{\script{1\over 2}}, -z]; (ii) [-x+2, y-{\script{1\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Related literature top

For the NMR and crystal structure of the asthma drug beclometasone dipropionate monohydrate, see: Othman et al. (2008); Duax et al. (1981).

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.

The brominated compound was isolated from the mother liquor of the first crystallization of beclomethasone dipropionate (10 g). This was dissolved in hexane:ethyl acetate (8:1 v/v) and eluted by flash-column silica gel chromatography with nitrogen at 20 psi. This procedure was repeated for other batches to accumulate more material. The combined fractions were further fractioniated on fresh silica gel. One of the fractions (162 mg) yielded crystals that were recrystallized from hexane:ethyl acetate (3:1 v/v) (47 mg); 490–491 K. Elemental analysis: Calc. for C28H36BrClO7: C 56.19, H 6.02, Br 13.21, Cl, 5.85%. Found: C 56.03, H 6.12, Br 12.97, Cl, 5.76% . MS+. 599.

Refinement top

Hydrogen atoms were placed at calculated positions (C–H 0.95–1.00 Å, O–H 0.82 Å) and were treated as riding on their parent carbon atoms, with U(H) set to 1.2–1.5 times Ueq(C,O).

The monoclinic unit cell emulates an orthorhombic unit cell as the β-angle is nearly a right angle. The twin law (-1 0 0 0 -1 0 0 0 1) showed that the major twin component is 60%.

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
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of one independent molecule of C28H36BrClO7 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
[Figure 2] Fig. 2. Thermal ellipsoid plot (Barbour, 2001) of the second independent molecule of C28H36BrClO7 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
(8S,9R,10S,11S,13S,14S,16S, 17R)-2-bromo-9α-chloro-11-hydroxy-10,13,16-trimethyl-3-oxo- 17-[2-(propionyloxy)acetyl]-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro- 3H-cyclopenta[a]phenanthren-17-yl propionate top
Crystal data top
C28H36BrClO7F(000) = 1248
Mr = 599.93Dx = 1.414 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 4369 reflections
a = 12.0999 (3) Åθ = 2.5–22.4°
b = 13.8673 (3) ŵ = 1.60 mm1
c = 16.7971 (4) ÅT = 140 K
β = 90.106 (1)°Plate, colorless
V = 2818.4 (1) Å30.22 × 0.11 × 0.02 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer
12754 independent reflections
Radiation source: fine-focus sealed tube9841 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
ω scansθmax = 27.5°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1515
Tmin = 0.642, Tmax = 0.746k = 1717
23151 measured reflectionsl = 2121
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.086 w = 1/[σ2(Fo2) + (0.0055P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.94(Δ/σ)max = 0.001
12754 reflectionsΔρmax = 0.61 e Å3
680 parametersΔρmin = 0.52 e Å3
1 restraintAbsolute structure: Flack (1983), 6028 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.001 (7)
Crystal data top
C28H36BrClO7V = 2818.4 (1) Å3
Mr = 599.93Z = 4
Monoclinic, P21Mo Kα radiation
a = 12.0999 (3) ŵ = 1.60 mm1
b = 13.8673 (3) ÅT = 140 K
c = 16.7971 (4) Å0.22 × 0.11 × 0.02 mm
β = 90.106 (1)°
Data collection top
Bruker SMART APEX
diffractometer
12754 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
9841 reflections with I > 2σ(I)
Tmin = 0.642, Tmax = 0.746Rint = 0.045
23151 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.086Δρmax = 0.61 e Å3
S = 0.94Δρmin = 0.52 e Å3
12754 reflectionsAbsolute structure: Flack (1983), 6028 Friedel pairs
680 parametersAbsolute structure parameter: 0.001 (7)
1 restraint
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.54075 (6)0.49998 (4)0.19693 (4)0.04545 (18)
Br20.47284 (6)0.38183 (4)0.69368 (4)0.04703 (18)
Cl10.31003 (12)0.21093 (9)0.14232 (8)0.0266 (3)
Cl20.67988 (12)0.69926 (9)0.65968 (7)0.0273 (3)
O10.6876 (4)0.3240 (3)0.2194 (3)0.0657 (16)
O20.2810 (3)0.3459 (2)0.0630 (2)0.0241 (9)
H20.23470.38570.07690.036*
O30.0895 (3)0.1241 (3)0.1469 (2)0.0288 (9)
O40.2209 (3)0.2617 (3)0.0927 (2)0.0288 (9)
O50.0790 (3)0.3584 (3)0.1263 (2)0.0286 (9)
O60.0029 (3)0.1104 (2)0.05595 (19)0.0188 (8)
O70.1480 (3)0.0108 (2)0.0430 (2)0.0258 (8)
O80.3216 (5)0.5484 (4)0.7329 (3)0.0651 (15)
O90.7133 (3)0.5636 (2)0.4572 (2)0.0234 (9)
H90.74950.51430.45070.035*
O101.0599 (3)0.8016 (2)0.3561 (2)0.0280 (9)
O111.2091 (3)0.6755 (3)0.4091 (2)0.0289 (9)
O121.0782 (3)0.5674 (3)0.3757 (3)0.0324 (10)
O130.9919 (3)0.8182 (2)0.56103 (18)0.0181 (8)
O141.1285 (3)0.9212 (2)0.5346 (2)0.0237 (8)
C10.4654 (4)0.3656 (4)0.0826 (3)0.0243 (12)
H10.41460.41540.06930.029*
C20.5368 (5)0.3808 (4)0.1419 (3)0.0327 (14)
C30.6175 (5)0.3074 (4)0.1685 (4)0.0369 (16)
C40.6101 (5)0.2152 (4)0.1282 (4)0.0350 (14)
H40.65840.16490.14460.042*
C50.5382 (5)0.1970 (4)0.0688 (3)0.0288 (13)
C60.4617 (4)0.2731 (3)0.0360 (3)0.0223 (12)
C70.5041 (5)0.2971 (4)0.0489 (3)0.0300 (14)
H7A0.58480.30240.04800.045*
H7B0.47210.35840.06660.045*
H7C0.48210.24570.08570.045*
C80.3392 (4)0.2315 (3)0.0368 (3)0.0195 (11)
C90.3330 (4)0.1346 (3)0.0066 (3)0.0200 (12)
H9a0.35330.14620.06350.024*
C100.4151 (4)0.0613 (3)0.0274 (4)0.0253 (13)
H10A0.39250.04410.08220.030*
H10B0.41280.00200.00530.030*
C110.5332 (5)0.1001 (4)0.0290 (4)0.0338 (14)
H11A0.58130.05420.05810.041*
H11B0.56120.10570.02610.041*
C120.2493 (4)0.3049 (3)0.0116 (3)0.0179 (11)
H120.24700.35770.05210.021*
C130.1328 (4)0.2587 (3)0.0063 (3)0.0184 (11)
H13A0.10600.24600.06090.022*
H13B0.08170.30560.01860.022*
C140.1283 (4)0.1650 (3)0.0409 (3)0.0159 (11)
C150.1439 (4)0.1828 (4)0.1301 (3)0.0227 (12)
H15A0.22170.19750.14090.034*
H15B0.09790.23740.14680.034*
H15C0.12220.12500.15990.034*
C160.2154 (4)0.0949 (3)0.0053 (3)0.0168 (11)
H160.19550.08580.05190.020*
C170.1884 (4)0.0007 (4)0.0474 (3)0.0224 (11)
H17A0.22140.05480.01890.027*
H17B0.21600.00130.10280.027*
C180.0620 (4)0.0044 (4)0.0457 (3)0.0165 (10)
H180.04250.04190.00310.020*
C190.0216 (4)0.1023 (3)0.0301 (3)0.0180 (11)
C200.0102 (5)0.0589 (3)0.1159 (3)0.0266 (13)
H20A0.04460.12260.12060.040*
H20B0.02220.02240.16510.040*
H20C0.06930.06640.10680.040*
C210.0750 (4)0.1418 (3)0.0776 (3)0.0213 (12)
C220.1497 (4)0.2152 (4)0.0356 (3)0.0247 (12)
H22A0.19490.18200.00510.030*
H22B0.10360.26420.00830.030*
C230.1728 (5)0.3310 (3)0.1386 (3)0.0238 (12)
C240.2494 (5)0.3645 (4)0.2015 (4)0.0364 (14)
H24A0.32420.37150.17840.044*
H24B0.25350.31470.24360.044*
C250.2165 (6)0.4583 (4)0.2385 (4)0.0375 (15)
H25A0.26780.47410.28180.056*
H25B0.14140.45300.25980.056*
H25C0.21870.50940.19820.056*
C260.0847 (4)0.0556 (3)0.0855 (3)0.0206 (12)
C270.0835 (5)0.0551 (4)0.1745 (3)0.0284 (13)
H27A0.03490.00210.19280.034*
H27B0.15910.04110.19370.034*
C280.0439 (6)0.1494 (4)0.2124 (3)0.0505 (17)
H28A0.04880.14440.27040.076*
H28B0.09050.20270.19390.076*
H28C0.03300.16150.19700.076*
C290.5366 (5)0.5327 (4)0.5906 (3)0.0254 (13)
H290.59060.48740.57370.030*
C300.4678 (5)0.5071 (5)0.6483 (3)0.0330 (14)
C310.3842 (6)0.5721 (5)0.6799 (4)0.0439 (18)
C320.3840 (5)0.6696 (5)0.6466 (4)0.0449 (18)
H320.33300.71520.66720.054*
C330.4528 (5)0.6975 (4)0.5883 (3)0.0287 (13)
C340.5335 (4)0.6289 (3)0.5506 (3)0.0212 (12)
C350.4887 (5)0.6095 (4)0.4648 (3)0.0274 (13)
H35A0.41280.58500.46800.041*
H35B0.53560.56160.43840.041*
H35C0.48960.66960.43420.041*
C360.6517 (4)0.6758 (4)0.5533 (3)0.0198 (11)
C370.7467 (4)0.6092 (3)0.5292 (3)0.0198 (12)
H370.75430.55830.57100.024*
C380.8584 (4)0.6604 (3)0.5215 (3)0.0192 (11)
H38A0.88630.67620.57540.023*
H38B0.91190.61580.49650.023*
C390.8529 (4)0.7532 (3)0.4722 (3)0.0168 (11)
C400.8294 (5)0.7317 (4)0.3834 (3)0.0240 (12)
H40A0.75320.70880.37740.036*
H40B0.88060.68190.36450.036*
H40C0.83960.79060.35210.036*
C410.7662 (4)0.8197 (3)0.5097 (3)0.0190 (11)
H410.78840.83060.56640.023*
C420.6501 (4)0.7747 (3)0.5103 (3)0.0223 (12)
H420.62820.76290.45370.027*
C430.5653 (5)0.8430 (4)0.5463 (4)0.0277 (13)
H43A0.59060.86270.59990.033*
H43B0.56060.90170.51290.033*
C440.4498 (5)0.7981 (4)0.5531 (4)0.0349 (15)
H44A0.40300.83990.58690.042*
H44B0.41560.79530.49950.042*
C450.7821 (4)0.9145 (3)0.4656 (3)0.0238 (12)
H45A0.74990.96900.49580.029*
H45B0.74770.91210.41210.029*
C460.9079 (4)0.9239 (3)0.4597 (3)0.0218 (12)
H460.93130.96600.50500.026*
C470.9425 (5)0.9759 (4)0.3841 (3)0.0341 (14)
H47A0.90901.04020.38300.051*
H47B0.91770.93900.33760.051*
H47C1.02320.98200.38300.051*
C480.9565 (4)0.8212 (3)0.4772 (3)0.0182 (11)
C491.0518 (5)0.7834 (3)0.4268 (3)0.0249 (12)
C501.1341 (5)0.7155 (4)0.4666 (3)0.0272 (12)
H50A1.17640.75120.50760.033*
H50B1.09360.66270.49340.033*
C511.1673 (5)0.6009 (4)0.3650 (3)0.0229 (12)
C521.2503 (5)0.5698 (4)0.3026 (4)0.0332 (14)
H52A1.32520.57040.32640.040*
H52B1.24950.61680.25830.040*
C531.2268 (5)0.4703 (4)0.2700 (4)0.0389 (16)
H53A1.28650.45110.23410.058*
H53B1.15660.47120.24070.058*
H53C1.22180.42420.31410.058*
C541.0753 (4)0.8780 (4)0.5826 (3)0.0223 (11)
C551.0950 (4)0.8777 (4)0.6712 (3)0.0205 (11)
H55A1.13450.81790.68630.025*
H55B1.02300.87810.69910.025*
C561.1626 (4)0.9647 (3)0.6976 (3)0.0291 (12)
H56A1.17510.96150.75520.044*
H56B1.12241.02400.68470.044*
H56C1.23390.96460.67000.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0424 (4)0.0454 (3)0.0485 (4)0.0172 (3)0.0005 (3)0.0155 (4)
Br20.0408 (4)0.0540 (4)0.0462 (4)0.0229 (3)0.0093 (3)0.0218 (4)
Cl10.0282 (7)0.0265 (7)0.0252 (7)0.0061 (6)0.0008 (5)0.0004 (6)
Cl20.0296 (7)0.0288 (7)0.0235 (6)0.0042 (6)0.0012 (6)0.0027 (6)
O10.061 (3)0.051 (3)0.085 (4)0.027 (3)0.052 (3)0.023 (3)
O20.018 (2)0.0180 (18)0.036 (2)0.0011 (15)0.0028 (16)0.0126 (16)
O30.027 (2)0.033 (2)0.027 (2)0.0012 (17)0.0083 (17)0.0044 (18)
O40.018 (2)0.0268 (19)0.042 (2)0.0001 (16)0.0097 (17)0.0128 (18)
O50.027 (2)0.029 (2)0.030 (2)0.0105 (16)0.0026 (17)0.0069 (17)
O60.023 (2)0.0160 (16)0.0180 (17)0.0030 (14)0.0040 (14)0.0002 (14)
O70.024 (2)0.0196 (18)0.033 (2)0.0063 (16)0.0001 (16)0.0000 (17)
O80.066 (4)0.075 (3)0.054 (3)0.031 (3)0.035 (3)0.007 (3)
O90.020 (2)0.0162 (18)0.034 (2)0.0022 (15)0.0036 (17)0.0077 (17)
O100.027 (2)0.0278 (19)0.029 (2)0.0021 (16)0.0040 (17)0.0047 (17)
O110.016 (2)0.0262 (19)0.044 (2)0.0025 (16)0.0029 (17)0.0063 (18)
O120.022 (2)0.030 (2)0.045 (3)0.0079 (17)0.0014 (19)0.0019 (19)
O130.0177 (19)0.0170 (17)0.0195 (17)0.0057 (14)0.0020 (14)0.0042 (14)
O140.027 (2)0.0197 (17)0.024 (2)0.0121 (16)0.0016 (17)0.0034 (16)
C10.021 (3)0.021 (3)0.031 (3)0.006 (3)0.004 (2)0.001 (2)
C20.036 (3)0.030 (3)0.032 (3)0.019 (3)0.002 (3)0.004 (3)
C30.031 (3)0.036 (3)0.044 (4)0.026 (3)0.020 (3)0.019 (3)
C40.023 (3)0.029 (3)0.053 (4)0.010 (3)0.006 (3)0.011 (3)
C50.018 (3)0.027 (3)0.042 (3)0.003 (3)0.001 (3)0.004 (3)
C60.016 (3)0.021 (3)0.029 (3)0.003 (2)0.000 (2)0.002 (2)
C70.021 (3)0.033 (3)0.036 (3)0.001 (2)0.008 (3)0.005 (3)
C80.021 (3)0.016 (2)0.021 (3)0.001 (2)0.000 (2)0.001 (2)
C90.021 (3)0.013 (2)0.026 (3)0.003 (2)0.001 (2)0.002 (2)
C100.018 (3)0.013 (2)0.045 (3)0.003 (2)0.000 (3)0.001 (3)
C110.029 (3)0.025 (3)0.047 (4)0.010 (3)0.004 (3)0.005 (3)
C120.011 (3)0.011 (2)0.032 (3)0.0002 (19)0.003 (2)0.005 (2)
C130.016 (3)0.013 (2)0.026 (3)0.001 (2)0.002 (2)0.002 (2)
C140.011 (2)0.013 (2)0.024 (3)0.0014 (19)0.001 (2)0.000 (2)
C150.025 (3)0.020 (3)0.023 (3)0.002 (2)0.004 (2)0.003 (2)
C160.017 (3)0.008 (2)0.026 (3)0.0011 (19)0.001 (2)0.004 (2)
C170.033 (3)0.010 (2)0.025 (3)0.000 (2)0.001 (2)0.000 (2)
C180.018 (3)0.017 (2)0.014 (2)0.000 (2)0.0024 (19)0.003 (2)
C190.025 (3)0.017 (2)0.012 (2)0.004 (2)0.004 (2)0.0023 (19)
C200.030 (3)0.021 (3)0.029 (3)0.004 (2)0.003 (2)0.004 (2)
C210.016 (3)0.020 (3)0.028 (3)0.007 (2)0.001 (2)0.000 (2)
C220.022 (3)0.020 (3)0.033 (3)0.003 (2)0.000 (2)0.005 (2)
C230.028 (3)0.017 (2)0.026 (3)0.001 (2)0.001 (2)0.002 (2)
C240.029 (3)0.040 (4)0.041 (3)0.003 (3)0.005 (3)0.001 (3)
C250.043 (4)0.032 (3)0.037 (3)0.003 (3)0.001 (3)0.012 (3)
C260.017 (3)0.014 (3)0.031 (3)0.005 (2)0.001 (2)0.005 (2)
C270.038 (3)0.023 (3)0.025 (3)0.004 (2)0.011 (2)0.006 (2)
C280.087 (5)0.039 (3)0.026 (3)0.005 (4)0.012 (3)0.002 (3)
C290.017 (3)0.028 (3)0.032 (3)0.002 (2)0.001 (3)0.004 (2)
C300.021 (3)0.048 (3)0.029 (3)0.015 (3)0.004 (3)0.008 (3)
C310.037 (4)0.048 (4)0.046 (4)0.024 (3)0.006 (3)0.009 (3)
C320.025 (3)0.052 (4)0.058 (4)0.002 (3)0.016 (3)0.034 (4)
C330.015 (3)0.026 (3)0.045 (3)0.002 (2)0.005 (3)0.011 (3)
C340.012 (3)0.021 (2)0.031 (3)0.004 (2)0.003 (2)0.003 (2)
C350.018 (3)0.032 (3)0.032 (3)0.006 (2)0.003 (2)0.001 (3)
C360.016 (3)0.020 (2)0.023 (3)0.003 (2)0.003 (2)0.003 (2)
C370.019 (3)0.012 (2)0.028 (3)0.003 (2)0.006 (2)0.001 (2)
C380.013 (3)0.016 (2)0.029 (3)0.001 (2)0.001 (2)0.000 (2)
C390.018 (3)0.018 (2)0.015 (2)0.000 (2)0.001 (2)0.002 (2)
C400.022 (3)0.017 (3)0.033 (3)0.004 (2)0.004 (2)0.000 (2)
C410.019 (3)0.010 (2)0.028 (3)0.004 (2)0.004 (2)0.006 (2)
C420.023 (3)0.015 (2)0.029 (3)0.002 (2)0.004 (2)0.001 (2)
C430.026 (3)0.018 (2)0.039 (3)0.012 (2)0.001 (2)0.002 (2)
C440.017 (3)0.029 (3)0.059 (4)0.009 (2)0.003 (3)0.010 (3)
C450.022 (3)0.018 (2)0.032 (3)0.002 (2)0.003 (2)0.001 (2)
C460.029 (3)0.015 (2)0.022 (3)0.003 (2)0.002 (2)0.004 (2)
C470.045 (4)0.025 (3)0.033 (3)0.004 (3)0.001 (3)0.012 (3)
C480.017 (3)0.016 (2)0.021 (3)0.002 (2)0.000 (2)0.001 (2)
C490.022 (3)0.020 (3)0.033 (3)0.009 (2)0.003 (2)0.000 (2)
C500.026 (3)0.027 (3)0.029 (3)0.002 (3)0.005 (2)0.005 (3)
C510.024 (3)0.016 (2)0.028 (3)0.003 (2)0.005 (2)0.001 (2)
C520.026 (3)0.045 (3)0.029 (3)0.001 (3)0.005 (3)0.005 (3)
C530.042 (4)0.043 (4)0.033 (3)0.007 (3)0.003 (3)0.001 (3)
C540.019 (3)0.015 (2)0.032 (3)0.002 (2)0.004 (2)0.001 (3)
C550.019 (2)0.020 (2)0.022 (3)0.001 (2)0.0003 (19)0.000 (2)
C560.030 (3)0.028 (3)0.029 (3)0.003 (2)0.003 (3)0.004 (3)
Geometric parameters (Å, º) top
Br1—C21.895 (6)C24—H24A0.9900
Br2—C301.898 (6)C24—H24B0.9900
Cl1—C81.830 (5)C25—H25A0.9800
Cl2—C361.847 (5)C25—H25B0.9800
O1—C31.224 (7)C25—H25C0.9800
O2—C121.428 (6)C26—C271.495 (7)
O2—H20.8200C27—C281.531 (7)
O3—C211.202 (6)C27—H27A0.9900
O4—C231.364 (6)C27—H27B0.9900
O4—C221.442 (6)C28—H28A0.9800
O5—C231.215 (6)C28—H28B0.9800
O6—C261.343 (6)C28—H28C0.9800
O6—C191.481 (6)C29—C301.328 (8)
O7—C261.217 (6)C29—C341.494 (7)
O8—C311.214 (8)C29—H290.9500
O9—C371.423 (6)C30—C311.455 (9)
O9—H90.8200C31—C321.464 (10)
O10—C491.217 (6)C32—C331.344 (8)
O11—C511.369 (6)C32—H320.9500
O11—C501.438 (6)C33—C341.505 (7)
O12—C511.187 (6)C33—C441.515 (8)
O13—C541.355 (6)C34—C351.562 (7)
O13—C481.472 (6)C34—C361.571 (7)
O14—C541.194 (6)C35—H35A0.9800
C1—C21.334 (8)C35—H35B0.9800
C1—C61.504 (7)C35—H35C0.9800
C1—H10.9500C36—C371.529 (7)
C2—C31.479 (9)C36—C421.551 (7)
C3—C41.450 (9)C37—C381.532 (7)
C4—C51.346 (8)C37—H371.0000
C4—H40.9500C38—C391.531 (7)
C5—C111.503 (8)C38—H38A0.9900
C5—C61.507 (7)C38—H38B0.9900
C6—C71.552 (8)C39—C401.547 (7)
C6—C81.590 (7)C39—C411.533 (7)
C7—H7A0.9800C39—C481.571 (7)
C7—H7B0.9800C40—H40A0.9800
C7—H7C0.9800C40—H40B0.9800
C8—C91.530 (7)C40—H40C0.9800
C8—C121.549 (7)C41—C451.521 (7)
C9—C161.526 (7)C41—C421.536 (7)
C9—C101.531 (7)C41—H411.0000
C9—H9a1.0000C42—C431.523 (7)
C10—C111.527 (8)C42—H421.0000
C10—H10A0.9900C43—C441.534 (8)
C10—H10B0.9900C43—H43A0.9900
C11—H11A0.9900C43—H43B0.9900
C11—H11B0.9900C44—H44A0.9900
C12—C131.551 (7)C44—H44B0.9900
C12—H121.0000C45—C461.531 (7)
C13—C141.523 (7)C45—H45A0.9900
C13—H13A0.9900C45—H45B0.9900
C13—H13B0.9900C46—C471.519 (7)
C14—C151.531 (7)C46—C481.568 (6)
C14—C161.552 (6)C46—H461.0000
C14—C191.568 (7)C47—H47A0.9800
C15—H15A0.9800C47—H47B0.9800
C15—H15B0.9800C47—H47C0.9800
C15—H15C0.9800C48—C491.525 (7)
C16—C171.521 (7)C49—C501.523 (7)
C16—H161.0000C50—H50A0.9900
C17—C181.531 (7)C50—H50B0.9900
C17—H17A0.9900C51—C521.515 (8)
C17—H17B0.9900C52—C531.510 (8)
C18—C201.534 (7)C52—H52A0.9900
C18—C191.579 (7)C52—H52B0.9900
C18—H181.0000C53—H53A0.9800
C19—C211.517 (7)C53—H53B0.9800
C20—H20A0.9800C53—H53C0.9800
C20—H20B0.9800C54—C551.507 (7)
C20—H20C0.9800C55—C561.523 (7)
C21—C221.534 (7)C55—H55A0.9900
C22—H22A0.9900C55—H55B0.9900
C22—H22B0.9900C56—H56A0.9800
C23—C241.479 (7)C56—H56B0.9800
C24—C251.496 (8)C56—H56C0.9800
C12—O2—H2109.5C27—C28—H28C109.5
C23—O4—C22115.8 (4)H28A—C28—H28C109.5
C26—O6—C19117.8 (4)H28B—C28—H28C109.5
C37—O9—H9109.5C30—C29—C34123.5 (5)
C51—O11—C50114.9 (4)C30—C29—H29118.3
C54—O13—C48117.0 (4)C34—C29—H29118.3
C2—C1—C6122.8 (5)C29—C30—C31122.6 (6)
C2—C1—H1118.6C29—C30—Br2121.2 (5)
C6—C1—H1118.6C31—C30—Br2116.2 (4)
C1—C2—C3122.9 (6)O8—C31—C32122.0 (7)
C1—C2—Br1121.2 (5)O8—C31—C30122.3 (7)
C3—C2—Br1115.9 (4)C32—C31—C30115.6 (6)
O1—C3—C4122.2 (6)C33—C32—C31123.0 (6)
O1—C3—C2122.5 (6)C33—C32—H32118.5
C4—C3—C2115.2 (5)C31—C32—H32118.5
C5—C4—C3123.4 (6)C32—C33—C34121.8 (5)
C5—C4—H4118.3C32—C33—C44122.4 (5)
C3—C4—H4118.3C34—C33—C44115.7 (5)
C4—C5—C11121.5 (5)C33—C34—C29113.1 (5)
C4—C5—C6122.4 (5)C33—C34—C35105.8 (4)
C11—C5—C6116.0 (5)C29—C34—C35105.6 (4)
C1—C6—C5112.9 (5)C33—C34—C36108.5 (4)
C1—C6—C7106.6 (4)C29—C34—C36109.6 (4)
C5—C6—C7106.4 (5)C35—C34—C36114.3 (5)
C1—C6—C8109.3 (4)C34—C35—H35A109.5
C5—C6—C8108.4 (4)C34—C35—H35B109.5
C7—C6—C8113.3 (4)H35A—C35—H35B109.5
C6—C7—H7A109.5C34—C35—H35C109.5
C6—C7—H7B109.5H35A—C35—H35C109.5
H7A—C7—H7B109.5H35B—C35—H35C109.5
C6—C7—H7C109.5C37—C36—C42114.8 (4)
H7A—C7—H7C109.5C37—C36—C34115.3 (4)
H7B—C7—H7C109.5C42—C36—C34110.0 (4)
C9—C8—C12114.4 (4)C37—C36—Cl2103.0 (4)
C9—C8—C6111.0 (4)C42—C36—Cl2107.3 (3)
C12—C8—C6114.4 (4)C34—C36—Cl2105.5 (4)
C9—C8—Cl1108.4 (3)O9—C37—C38112.5 (4)
C12—C8—Cl1103.4 (3)O9—C37—C36106.3 (4)
C6—C8—Cl1104.3 (3)C38—C37—C36114.0 (4)
C16—C9—C8110.8 (4)O9—C37—H37107.9
C16—C9—C10111.1 (4)C38—C37—H37107.9
C8—C9—C10111.9 (4)C36—C37—H37107.9
C16—C9—H9a107.6C39—C38—C37113.5 (4)
C8—C9—H9a107.6C39—C38—H38A108.9
C10—C9—H9a107.6C37—C38—H38A108.9
C11—C10—C9112.3 (4)C39—C38—H38B108.9
C11—C10—H10A109.1C37—C38—H38B108.9
C9—C10—H10A109.1H38A—C38—H38B107.7
C11—C10—H10B109.1C38—C39—C40111.5 (4)
C9—C10—H10B109.1C38—C39—C41108.2 (4)
H10A—C10—H10B107.9C40—C39—C41112.8 (4)
C5—C11—C10111.1 (5)C38—C39—C48116.2 (4)
C5—C11—H11A109.4C40—C39—C48108.2 (4)
C10—C11—H11A109.4C41—C39—C4899.4 (4)
C5—C11—H11B109.4C39—C40—H40A109.5
C10—C11—H11B109.4C39—C40—H40B109.5
H11A—C11—H11B108.0H40A—C40—H40B109.5
O2—C12—C8108.2 (4)C39—C40—H40C109.5
O2—C12—C13111.1 (4)H40A—C40—H40C109.5
C8—C12—C13112.4 (4)H40B—C40—H40C109.5
O2—C12—H12108.3C45—C41—C42118.0 (4)
C8—C12—H12108.3C45—C41—C39103.4 (4)
C13—C12—H12108.3C42—C41—C39112.6 (4)
C14—C13—C12114.5 (4)C45—C41—H41107.4
C14—C13—H13A108.6C42—C41—H41107.4
C12—C13—H13A108.6C39—C41—H41107.4
C14—C13—H13B108.6C43—C42—C41111.5 (4)
C12—C13—H13B108.6C43—C42—C36111.9 (4)
H13A—C13—H13B107.6C41—C42—C36110.6 (4)
C13—C14—C15111.6 (4)C43—C42—H42107.5
C13—C14—C16108.1 (4)C41—C42—H42107.5
C15—C14—C16113.2 (4)C36—C42—H42107.5
C13—C14—C19116.2 (4)C44—C43—C42113.1 (4)
C15—C14—C19107.8 (4)C44—C43—H43A109.0
C16—C14—C1999.6 (4)C42—C43—H43A109.0
C14—C15—H15A109.5C44—C43—H43B109.0
C14—C15—H15B109.5C42—C43—H43B109.0
H15A—C15—H15B109.5H43A—C43—H43B107.8
C14—C15—H15C109.5C33—C44—C43112.4 (5)
H15A—C15—H15C109.5C33—C44—H44A109.1
H15B—C15—H15C109.5C43—C44—H44A109.1
C17—C16—C9120.2 (4)C33—C44—H44B109.1
C17—C16—C14102.4 (4)C43—C44—H44B109.1
C9—C16—C14113.6 (4)H44A—C44—H44B107.8
C17—C16—H16106.6C41—C45—C46103.4 (4)
C9—C16—H16106.6C41—C45—H45A111.1
C14—C16—H16106.6C46—C45—H45A111.1
C16—C17—C18104.2 (4)C41—C45—H45B111.1
C16—C17—H17A110.9C46—C45—H45B111.1
C18—C17—H17A110.9H45A—C45—H45B109.0
C16—C17—H17B110.9C47—C46—C45111.8 (4)
C18—C17—H17B110.9C47—C46—C48118.9 (5)
H17A—C17—H17B108.9C45—C46—C48106.5 (4)
C20—C18—C17114.5 (4)C47—C46—H46106.3
C20—C18—C19117.5 (4)C45—C46—H46106.3
C17—C18—C19105.6 (4)C48—C46—H46106.3
C20—C18—H18106.1C46—C47—H47A109.5
C17—C18—H18106.1C46—C47—H47B109.5
C19—C18—H18106.1H47A—C47—H47B109.5
O6—C19—C21109.3 (4)C46—C47—H47C109.5
O6—C19—C14103.8 (4)H47A—C47—H47C109.5
C21—C19—C14111.9 (4)H47B—C47—H47C109.5
O6—C19—C18107.2 (4)O13—C48—C49107.6 (4)
C21—C19—C18119.3 (4)O13—C48—C46108.3 (4)
C14—C19—C18104.2 (4)C49—C48—C46119.5 (4)
C18—C20—H20A109.5O13—C48—C39105.4 (4)
C18—C20—H20B109.5C49—C48—C39111.6 (4)
H20A—C20—H20B109.5C46—C48—C39103.7 (4)
C18—C20—H20C109.5O10—C49—C48122.1 (5)
H20A—C20—H20C109.5O10—C49—C50120.1 (5)
H20B—C20—H20C109.5C48—C49—C50117.6 (4)
O3—C21—C19123.1 (5)O11—C50—C49110.9 (4)
O3—C21—C22119.7 (5)O11—C50—H50A109.4
C19—C21—C22116.9 (4)C49—C50—H50A109.4
O4—C22—C21110.0 (4)O11—C50—H50B109.4
O4—C22—H22A109.7C49—C50—H50B109.4
C21—C22—H22A109.7H50A—C50—H50B108.0
O4—C22—H22B109.7O12—C51—O11123.2 (5)
C21—C22—H22B109.7O12—C51—C52126.6 (5)
H22A—C22—H22B108.2O11—C51—C52110.2 (5)
O5—C23—O4121.6 (5)C51—C52—C53112.7 (5)
O5—C23—C24127.5 (5)C51—C52—H52A109.1
O4—C23—C24110.9 (5)C53—C52—H52A109.1
C23—C24—C25113.7 (5)C51—C52—H52B109.1
C23—C24—H24A108.8C53—C52—H52B109.1
C25—C24—H24A108.8H52A—C52—H52B107.8
C23—C24—H24B108.8C52—C53—H53A109.5
C25—C24—H24B108.8C52—C53—H53B109.5
H24A—C24—H24B107.7H53A—C53—H53B109.5
C24—C25—H25A109.5C52—C53—H53C109.5
C24—C25—H25B109.5H53A—C53—H53C109.5
H25A—C25—H25B109.5H53B—C53—H53C109.5
C24—C25—H25C109.5O14—C54—O13121.9 (5)
H25A—C25—H25C109.5O14—C54—C55125.8 (5)
H25B—C25—H25C109.5O13—C54—C55112.2 (4)
O7—C26—O6122.4 (5)C54—C55—C56111.7 (4)
O7—C26—C27126.1 (5)C54—C55—H55A109.3
O6—C26—C27111.5 (5)C56—C55—H55A109.3
C26—C27—C28114.4 (4)C54—C55—H55B109.3
C26—C27—H27A108.6C56—C55—H55B109.3
C28—C27—H27A108.6H55A—C55—H55B107.9
C26—C27—H27B108.6C55—C56—H56A109.5
C28—C27—H27B108.6C55—C56—H56B109.5
H27A—C27—H27B107.6H56A—C56—H56B109.5
C27—C28—H28A109.5C55—C56—H56C109.5
C27—C28—H28B109.5H56A—C56—H56C109.5
H28A—C28—H28B109.5H56B—C56—H56C109.5
C6—C1—C2—C31.3 (9)C34—C29—C30—C311.7 (9)
C6—C1—C2—Br1178.3 (4)C34—C29—C30—Br2177.6 (4)
C1—C2—C3—O1175.1 (6)C29—C30—C31—O8179.9 (6)
Br1—C2—C3—O14.5 (9)Br2—C30—C31—O80.8 (8)
C1—C2—C3—C43.0 (9)C29—C30—C31—C322.9 (9)
Br1—C2—C3—C4177.3 (4)Br2—C30—C31—C32177.8 (5)
O1—C3—C4—C5175.9 (6)O8—C31—C32—C33179.7 (6)
C2—C3—C4—C52.2 (9)C30—C31—C32—C332.7 (9)
C3—C4—C5—C11179.7 (6)C31—C32—C33—C342.0 (9)
C3—C4—C5—C62.9 (10)C31—C32—C33—C44178.6 (6)
C2—C1—C6—C56.0 (7)C32—C33—C34—C296.2 (8)
C2—C1—C6—C7110.5 (6)C44—C33—C34—C29177.1 (5)
C2—C1—C6—C8126.7 (5)C32—C33—C34—C35108.9 (6)
C4—C5—C6—C16.8 (8)C44—C33—C34—C3567.8 (5)
C11—C5—C6—C1175.7 (5)C32—C33—C34—C36128.0 (6)
C4—C5—C6—C7109.8 (6)C44—C33—C34—C3655.3 (6)
C11—C5—C6—C767.7 (6)C30—C29—C34—C336.1 (8)
C4—C5—C6—C8128.0 (6)C30—C29—C34—C35109.1 (6)
C11—C5—C6—C854.5 (6)C30—C29—C34—C36127.3 (6)
C1—C6—C8—C9177.2 (4)C33—C34—C36—C37170.9 (5)
C5—C6—C8—C953.8 (6)C29—C34—C36—C3747.0 (6)
C7—C6—C8—C964.1 (5)C35—C34—C36—C3771.3 (6)
C1—C6—C8—C1251.5 (6)C33—C34—C36—C4257.4 (6)
C5—C6—C8—C12174.9 (4)C29—C34—C36—C42178.7 (4)
C7—C6—C8—C1267.3 (6)C35—C34—C36—C4260.4 (5)
C1—C6—C8—Cl160.7 (4)C33—C34—C36—Cl258.0 (5)
C5—C6—C8—Cl162.7 (5)C29—C34—C36—Cl265.9 (5)
C7—C6—C8—Cl1179.4 (4)C35—C34—C36—Cl2175.8 (3)
C12—C8—C9—C1648.9 (6)C42—C36—C37—O981.9 (5)
C6—C8—C9—C16179.8 (4)C34—C36—C37—O947.6 (6)
Cl1—C8—C9—C1665.8 (5)Cl2—C36—C37—O9161.9 (3)
C12—C8—C9—C10173.5 (4)C42—C36—C37—C3842.7 (6)
C6—C8—C9—C1055.2 (6)C34—C36—C37—C38172.1 (4)
Cl1—C8—C9—C1058.8 (5)Cl2—C36—C37—C3873.6 (5)
C16—C9—C10—C11178.4 (5)O9—C37—C38—C3972.8 (5)
C8—C9—C10—C1154.0 (6)C36—C37—C38—C3948.3 (6)
C4—C5—C11—C10128.5 (6)C37—C38—C39—C4068.4 (6)
C6—C5—C11—C1054.0 (7)C37—C38—C39—C4156.2 (5)
C9—C10—C11—C551.4 (7)C37—C38—C39—C48166.9 (4)
C9—C8—C12—O277.7 (5)C38—C39—C41—C45170.5 (4)
C6—C8—C12—O252.0 (5)C40—C39—C41—C4565.7 (5)
Cl1—C8—C12—O2164.7 (3)C48—C39—C41—C4548.8 (5)
C9—C8—C12—C1345.3 (6)C38—C39—C41—C4260.9 (5)
C6—C8—C12—C13175.0 (4)C40—C39—C41—C4262.9 (5)
Cl1—C8—C12—C1372.2 (4)C48—C39—C41—C42177.3 (4)
O2—C12—C13—C1472.4 (5)C45—C41—C42—C4358.4 (6)
C8—C12—C13—C1449.0 (6)C39—C41—C42—C43178.8 (4)
C12—C13—C14—C1570.9 (5)C45—C41—C42—C36176.4 (4)
C12—C13—C14—C1654.1 (5)C39—C41—C42—C3656.0 (6)
C12—C13—C14—C19164.9 (4)C37—C36—C42—C43170.9 (5)
C8—C9—C16—C17177.9 (4)C34—C36—C42—C4357.1 (6)
C10—C9—C16—C1757.0 (6)Cl2—C36—C42—C4357.1 (5)
C8—C9—C16—C1456.3 (6)C37—C36—C42—C4145.9 (6)
C10—C9—C16—C14178.7 (5)C34—C36—C42—C41177.9 (4)
C13—C14—C16—C17170.5 (4)Cl2—C36—C42—C4167.9 (4)
C15—C14—C16—C1765.4 (5)C41—C42—C43—C44176.1 (5)
C19—C14—C16—C1748.8 (5)C36—C42—C43—C4451.6 (7)
C13—C14—C16—C958.4 (6)C32—C33—C44—C43133.0 (6)
C15—C14—C16—C965.7 (6)C34—C33—C44—C4350.3 (7)
C19—C14—C16—C9179.9 (4)C42—C43—C44—C3346.7 (7)
C9—C16—C17—C18170.0 (4)C42—C41—C45—C46166.4 (4)
C14—C16—C17—C1842.9 (5)C39—C41—C45—C4641.3 (5)
C16—C17—C18—C20150.3 (4)C41—C45—C46—C47148.0 (4)
C16—C17—C18—C1919.3 (5)C41—C45—C46—C4816.7 (5)
C26—O6—C19—C2167.2 (5)C54—O13—C48—C4966.3 (5)
C26—O6—C19—C14173.3 (4)C54—O13—C48—C4664.1 (5)
C26—O6—C19—C1863.4 (5)C54—O13—C48—C39174.5 (4)
C13—C14—C19—O639.6 (5)C47—C46—C48—O13134.3 (5)
C15—C14—C19—O6165.7 (4)C45—C46—C48—O1398.5 (4)
C16—C14—C19—O676.1 (4)C47—C46—C48—C4910.8 (7)
C13—C14—C19—C2178.1 (5)C45—C46—C48—C49138.0 (5)
C15—C14—C19—C2148.0 (5)C47—C46—C48—C39114.1 (5)
C16—C14—C19—C21166.3 (4)C45—C46—C48—C3913.1 (5)
C13—C14—C19—C18151.7 (4)C38—C39—C48—O1339.2 (5)
C15—C14—C19—C1882.2 (4)C40—C39—C48—O13165.5 (4)
C16—C14—C19—C1836.0 (5)C41—C39—C48—O1376.6 (4)
C20—C18—C19—O6132.2 (4)C38—C39—C48—C4977.3 (5)
C17—C18—C19—O698.6 (4)C40—C39—C48—C4949.0 (5)
C20—C18—C19—C217.4 (6)C41—C39—C48—C49167.0 (4)
C17—C18—C19—C21136.7 (5)C38—C39—C48—C46152.9 (4)
C20—C18—C19—C14118.2 (4)C40—C39—C48—C4680.8 (5)
C17—C18—C19—C1411.0 (5)C41—C39—C48—C4637.1 (5)
O6—C19—C21—O3161.9 (5)O13—C48—C49—O10159.1 (4)
C14—C19—C21—O383.8 (6)C46—C48—C49—O1035.2 (7)
C18—C19—C21—O338.1 (7)C39—C48—C49—O1085.8 (6)
O6—C19—C21—C2224.2 (5)O13—C48—C49—C5024.9 (6)
C14—C19—C21—C2290.2 (5)C46—C48—C49—C50148.8 (4)
C18—C19—C21—C22147.9 (4)C39—C48—C49—C5090.2 (5)
C23—O4—C22—C2176.7 (5)C51—O11—C50—C4978.9 (5)
O3—C21—C22—O47.2 (7)O10—C49—C50—O114.3 (7)
C19—C21—C22—O4167.0 (4)C48—C49—C50—O11171.7 (4)
C22—O4—C23—O57.2 (7)C50—O11—C51—O124.2 (7)
C22—O4—C23—C24172.7 (4)C50—O11—C51—C52175.8 (4)
O5—C23—C24—C2516.9 (8)O12—C51—C52—C5318.3 (8)
O4—C23—C24—C25163.2 (5)O11—C51—C52—C53161.7 (5)
C19—O6—C26—O710.5 (7)C48—O13—C54—O1410.4 (7)
C19—O6—C26—C27167.5 (4)C48—O13—C54—C55172.9 (4)
O7—C26—C27—C28149.2 (5)O14—C54—C55—C5620.5 (7)
O6—C26—C27—C2832.9 (7)O13—C54—C55—C56162.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O7i0.822.112.817 (5)145
O9—H9···O14ii0.821.982.754 (5)158
Symmetry codes: (i) x, y+1/2, z; (ii) x+2, y1/2, z+1.

Experimental details

Crystal data
Chemical formulaC28H36BrClO7
Mr599.93
Crystal system, space groupMonoclinic, P21
Temperature (K)140
a, b, c (Å)12.0999 (3), 13.8673 (3), 16.7971 (4)
β (°) 90.106 (1)
V3)2818.4 (1)
Z4
Radiation typeMo Kα
µ (mm1)1.60
Crystal size (mm)0.22 × 0.11 × 0.02
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.642, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
23151, 12754, 9841
Rint0.045
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.086, 0.94
No. of reflections12754
No. of parameters680
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.61, 0.52
Absolute structureFlack (1983), 6028 Friedel pairs
Absolute structure parameter0.001 (7)

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O7i0.822.112.817 (5)145
O9—H9···O14ii0.821.982.754 (5)158
Symmetry codes: (i) x, y+1/2, z; (ii) x+2, y1/2, z+1.
 

Acknowledgements

We thank the University of Malaya for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationDuax, W. L., Cody, V. & Strong, P. D. (1981). Acta Cryst. B37, 383–387.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationOthman, A., Harris, R. K., Hodgkinson, P., Christopher, E. A. & Lancaster, R. W. (2008). New J. Chem. 32, 1796–1806.  Web of Science CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar

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