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

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ISSN: 2056-9890

9α-Bromo analog of beclometasone dipropionate monohydrate

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 (8S,9R,10S,11S,13S,14S,16S,17R)-9α-bromo-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 monohydrate, C28H37BrO7·H2O, which has a 9α-Br atom in place of the 9α-Cl atom of monohydrated beclometasone dipropionate, one six-membered ring is planar (r.m.s. deviation = 0.02 Å) owing to its 1,4-diene-3-one composition, whereas the two other six-membered rings each have a chair conformation. The organic mol­ecule and water mol­ecules engage in hydrogen-bonding inter­actions, generating a helical chain running along the c axis of the ortho­rhom­bic unit cell.

Related literature

For the NMR data and the 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.]). The two compounds are isostructural.

[Scheme 1]

Experimental

Crystal data
  • C28H37BrO7·H2O

  • Mr = 583.50

  • Orthorhombic, P 21 21 21

  • a = 11.9565 (2) Å

  • b = 14.1329 (2) Å

  • c = 16.1648 (3) Å

  • V = 2731.53 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.55 mm−1

  • T = 140 K

  • 0.40 × 0.08 × 0.08 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.611, Tmax = 0.746 (expected range = 0.723–0.883)

  • 18917 measured reflections

  • 6226 independent reflections

  • 5575 reflections with I > 2σ(I)

  • Rint = 0.028

Refinement
  • R[F2 > 2σ(F2)] = 0.026

  • wR(F2) = 0.055

  • S = 0.96

  • 6226 reflections

  • 351 parameters

  • 4 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.39 e Å−3

  • Δρmin = −0.25 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2717 Friedel pairs

  • Flack parameter: 0.001 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2⋯O1w 0.83 (1) 1.93 (1) 2.759 (2) 173 (2)
O1w—H11⋯O5 0.84 (1) 2.06 (1) 2.859 (2) 159 (3)
O1w—H12⋯O7i 0.84 (1) 2.03 (1) 2.854 (2) 168 (2)
Symmetry code: (i) [-x+{\script{3\over 2}}, -y+2, z-{\script{1\over 2}}].

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). The two compounds are isostructural.

Experimental top

17α,21-Dihydroxy-16β-methylpregna-1,4,9-triene-3,20-dionedipropionate (5.5 g) was reacted with bromodan (1,3-dibromo-5,5-dimethylhydantion) (4.8 g) to give a yellow product (6.6 g). TLC showed one major product and five minor ones. The major product (3.0 g) was initially recrystallized three times, once from chloroform-methanol (1:2 v/v), and the second and third times from hexane-methanol (1:1 v/v). The recovered material (1.8 g). was then divided for two different recrystallizations.

Recrystallization form ethyl acetate-methanol (1:9 v/v) gave a white powder, m.p. 453–455 K. Elemental analysis: Calc. for C28H37BrO7 (mol. wt. 564): C 59.47, H 6.59, Br 14.13%. Found: C 59.3, H 6.57, Br 13.83%.

Recrystallization from methanol water gave colorless crystals, m.p. 460–461 K. Elemental analysis: Calc. for C22H37BrO7.H2O (mol. wt. 582): C 57.64, H 6.69, Br 13.70%. Found: C 57.68, H 6.78, Br 13.46%. The water molecule was detected from the 1H-NMR spectrum. Thermogravimetric analysis showed a peak at 365 K that corresponded to the loss of water.

Refinement top

Hydrogen atoms were placed at calculated positions (C–H 0.95–1.00 Å) and were treated as riding on their parent carbon atoms, with U(H) set to 1.2–1.5 times Ueq(C). The O-H atoms were refined with 0.84 (1) Å and with U(H) set to 1.5 times Ueq(O).

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 C28H37BrO7.H2O at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
8S,9R,10S,11S,13S,14S,16S, 17R)-9α-bromo-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 monohydrate top
Crystal data top
C28H37BrO7·H2OF(000) = 1224
Mr = 583.50Dx = 1.419 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 7177 reflections
a = 11.9565 (2) Åθ = 2.2–28.2°
b = 14.1329 (2) ŵ = 1.55 mm1
c = 16.1648 (3) ÅT = 140 K
V = 2731.53 (8) Å3Prism, brown
Z = 40.40 × 0.08 × 0.08 mm
Data collection top
Bruker SMART APEX
diffractometer
6226 independent reflections
Radiation source: fine-focus sealed tube5575 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
ω scansθmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1515
Tmin = 0.611, Tmax = 0.746k = 1818
18917 measured reflectionsl = 2021
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)] = 0.026H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.055 w = 1/[σ2(Fo2) + (0.0102P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max = 0.001
6226 reflectionsΔρmax = 0.39 e Å3
351 parametersΔρmin = 0.25 e Å3
4 restraintsAbsolute structure: Flack (1983), 2717 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.001 (5)
Crystal data top
C28H37BrO7·H2OV = 2731.53 (8) Å3
Mr = 583.50Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 11.9565 (2) ŵ = 1.55 mm1
b = 14.1329 (2) ÅT = 140 K
c = 16.1648 (3) Å0.40 × 0.08 × 0.08 mm
Data collection top
Bruker SMART APEX
diffractometer
6226 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
5575 reflections with I > 2σ(I)
Tmin = 0.611, Tmax = 0.746Rint = 0.028
18917 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.026H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.055Δρmax = 0.39 e Å3
S = 0.96Δρmin = 0.25 e Å3
6226 reflectionsAbsolute structure: Flack (1983), 2717 Friedel pairs
351 parametersAbsolute structure parameter: 0.001 (5)
4 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.657482 (17)0.615717 (12)0.957131 (12)0.01918 (5)
O10.66966 (16)0.34385 (10)0.78558 (10)0.0357 (4)
O20.81449 (12)0.80839 (9)0.80872 (9)0.0228 (3)
H20.8635 (13)0.8476 (11)0.8218 (12)0.018 (6)*
O30.67741 (12)1.10469 (9)1.01228 (9)0.0272 (3)
O40.86491 (12)1.09748 (9)1.10396 (9)0.0247 (3)
O50.93019 (13)1.02972 (10)0.98878 (9)0.0275 (4)
O60.64117 (12)0.87198 (8)1.09415 (7)0.0177 (3)
O70.56588 (13)0.95956 (9)1.19554 (9)0.0233 (3)
O1W0.98752 (14)0.93262 (10)0.83951 (10)0.0274 (3)
H110.989 (2)0.9626 (15)0.8845 (8)0.042 (8)*
H120.975 (3)0.9715 (14)0.8012 (10)0.061 (10)*
C10.6947 (2)0.69388 (14)0.69871 (12)0.0247 (5)
H1A0.68440.65030.65210.037*
H1B0.76950.72220.69570.037*
H1C0.63810.74390.69610.037*
C20.68233 (17)0.63823 (12)0.78206 (12)0.0191 (4)
C30.78273 (19)0.57607 (15)0.78750 (13)0.0225 (5)
H30.85370.60580.79230.027*
C40.7804 (2)0.48178 (14)0.78608 (13)0.0249 (5)
H40.84870.44740.78730.030*
C50.6745 (2)0.43061 (14)0.78268 (13)0.0250 (5)
C60.57302 (19)0.48835 (14)0.77512 (12)0.0222 (5)
H60.50310.45700.76960.027*
C70.57411 (18)0.58267 (14)0.77566 (12)0.0195 (4)
C80.46949 (17)0.64072 (13)0.77038 (13)0.0207 (4)
H8A0.40360.59830.76930.025*
H8B0.47000.67790.71850.025*
C90.46048 (17)0.70818 (13)0.84465 (13)0.0198 (4)
H9A0.39630.75140.83620.024*
H9B0.44600.67090.89540.024*
C100.56683 (17)0.76670 (12)0.85667 (12)0.0165 (4)
H100.57430.80980.80800.020*
C110.67279 (18)0.70477 (12)0.86053 (11)0.0159 (4)
C120.78016 (17)0.76116 (13)0.88200 (12)0.0178 (4)
H12A0.83970.71460.89700.021*
C130.76505 (16)0.82939 (12)0.95594 (13)0.0162 (4)
H13A0.75970.79191.00750.019*
H13B0.83190.87040.96030.019*
C140.66039 (16)0.89215 (11)0.94808 (11)0.0156 (3)
C150.67492 (18)0.96648 (13)0.87915 (11)0.0197 (4)
H15A0.67750.93470.82530.030*
H15B0.74481.00130.88800.030*
H15C0.61181.01070.88030.030*
C160.55793 (17)0.82829 (13)0.93416 (12)0.0158 (4)
H160.55380.78430.98250.019*
C170.46005 (16)0.89684 (13)0.94236 (12)0.0196 (4)
H17A0.38900.86250.95180.023*
H17B0.45250.93670.89230.023*
C180.49199 (17)0.95706 (13)1.01841 (12)0.0188 (4)
H180.45560.92651.06730.023*
C190.44583 (19)1.05760 (13)1.01391 (14)0.0266 (5)
H19A0.46661.09221.06420.040*
H19B0.36421.05531.00920.040*
H19C0.47711.08990.96550.040*
C200.62151 (17)0.94357 (12)1.02997 (12)0.0172 (4)
C210.69204 (16)1.03130 (12)1.04845 (13)0.0194 (4)
C220.78712 (19)1.02089 (14)1.11030 (13)0.0237 (5)
H22A0.75601.01901.16700.028*
H22B0.82660.96041.10020.028*
C230.93404 (17)1.09329 (12)1.03848 (14)0.0223 (4)
C241.01341 (19)1.17575 (13)1.03599 (16)0.0292 (5)
H24A1.03131.19491.09340.035*
H24B0.97581.22981.00870.035*
C251.1207 (2)1.15487 (16)0.99096 (16)0.0361 (6)
H25A1.16571.21260.98750.054*
H25B1.10361.13220.93510.054*
H25C1.16251.10611.02100.054*
C260.60442 (16)0.88507 (15)1.17195 (11)0.0194 (4)
C270.6195 (2)0.79691 (15)1.22196 (13)0.0289 (5)
H27A0.57400.74591.19680.035*
H27B0.69890.77741.21860.035*
C280.5879 (3)0.80587 (18)1.31099 (15)0.0490 (8)
H28A0.60520.74671.33990.074*
H28B0.50770.81901.31540.074*
H28C0.63030.85781.33620.074*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.02274 (10)0.01686 (8)0.01795 (8)0.00030 (8)0.00010 (9)0.00231 (8)
O10.0466 (12)0.0182 (7)0.0421 (10)0.0026 (8)0.0022 (9)0.0055 (7)
O20.0226 (9)0.0247 (7)0.0211 (7)0.0069 (6)0.0043 (7)0.0014 (6)
O30.0291 (9)0.0165 (6)0.0361 (8)0.0000 (6)0.0037 (7)0.0020 (6)
O40.0224 (9)0.0257 (7)0.0261 (7)0.0047 (6)0.0011 (6)0.0071 (6)
O50.0310 (9)0.0239 (7)0.0276 (8)0.0022 (7)0.0026 (7)0.0074 (6)
O60.0216 (8)0.0173 (6)0.0143 (6)0.0028 (6)0.0019 (6)0.0018 (5)
O70.0281 (9)0.0220 (7)0.0197 (7)0.0036 (6)0.0027 (7)0.0024 (6)
O1W0.0315 (9)0.0279 (8)0.0227 (8)0.0049 (7)0.0016 (8)0.0012 (7)
C10.0295 (13)0.0280 (10)0.0167 (10)0.0050 (9)0.0023 (9)0.0016 (9)
C20.0230 (12)0.0189 (9)0.0154 (9)0.0001 (7)0.0016 (8)0.0032 (7)
C30.0189 (12)0.0286 (10)0.0201 (11)0.0006 (9)0.0001 (9)0.0060 (9)
C40.0265 (13)0.0236 (10)0.0247 (11)0.0069 (9)0.0007 (10)0.0061 (9)
C50.0322 (15)0.0238 (10)0.0191 (10)0.0031 (10)0.0026 (11)0.0045 (8)
C60.0248 (12)0.0252 (10)0.0165 (10)0.0048 (9)0.0005 (9)0.0045 (8)
C70.0231 (12)0.0231 (9)0.0122 (9)0.0011 (9)0.0013 (9)0.0029 (8)
C80.0191 (11)0.0221 (10)0.0210 (10)0.0036 (8)0.0017 (9)0.0032 (8)
C90.0170 (11)0.0199 (9)0.0224 (10)0.0003 (8)0.0010 (9)0.0033 (8)
C100.0182 (11)0.0150 (9)0.0162 (10)0.0001 (8)0.0005 (9)0.0006 (7)
C110.0197 (11)0.0153 (8)0.0126 (9)0.0008 (8)0.0014 (9)0.0012 (7)
C120.0161 (11)0.0183 (9)0.0188 (10)0.0012 (8)0.0001 (9)0.0013 (8)
C130.0142 (10)0.0172 (8)0.0172 (9)0.0006 (7)0.0018 (9)0.0004 (9)
C140.0166 (9)0.0138 (7)0.0164 (8)0.0012 (9)0.0004 (9)0.0009 (8)
C150.0213 (12)0.0198 (9)0.0180 (9)0.0014 (8)0.0005 (9)0.0044 (8)
C160.0142 (10)0.0167 (9)0.0167 (10)0.0002 (7)0.0009 (8)0.0015 (7)
C170.0174 (10)0.0201 (9)0.0211 (11)0.0027 (8)0.0014 (8)0.0010 (8)
C180.0180 (11)0.0178 (9)0.0206 (10)0.0013 (8)0.0012 (8)0.0002 (8)
C190.0231 (12)0.0226 (10)0.0340 (12)0.0070 (9)0.0008 (10)0.0039 (9)
C200.0207 (10)0.0155 (8)0.0155 (10)0.0011 (7)0.0014 (8)0.0015 (8)
C210.0198 (11)0.0189 (8)0.0195 (10)0.0033 (7)0.0026 (9)0.0041 (9)
C220.0254 (12)0.0251 (10)0.0207 (11)0.0049 (9)0.0005 (9)0.0005 (9)
C230.0232 (11)0.0201 (9)0.0235 (10)0.0025 (7)0.0033 (10)0.0004 (9)
C240.0259 (12)0.0223 (9)0.0393 (13)0.0027 (8)0.0008 (12)0.0035 (11)
C250.0328 (15)0.0304 (11)0.0450 (14)0.0057 (10)0.0047 (12)0.0026 (11)
C260.0166 (10)0.0225 (9)0.0191 (10)0.0013 (9)0.0005 (8)0.0016 (9)
C270.0391 (15)0.0229 (10)0.0246 (11)0.0033 (10)0.0046 (10)0.0065 (9)
C280.082 (2)0.0397 (14)0.0253 (12)0.0159 (14)0.0129 (15)0.0137 (11)
Geometric parameters (Å, º) top
Br1—C112.0140 (17)C12—H12A1.0000
O1—C51.228 (2)C13—C141.539 (2)
O2—C121.420 (2)C13—H13A0.9900
O2—H20.834 (9)C13—H13B0.9900
O3—C211.203 (2)C14—C161.538 (3)
O4—C231.344 (3)C14—C151.541 (2)
O4—C221.431 (2)C14—C201.580 (2)
O5—C231.206 (2)C15—H15A0.9800
O6—C261.345 (2)C15—H15B0.9800
O6—C201.468 (2)C15—H15C0.9800
O7—C261.211 (2)C16—C171.525 (3)
O1W—H110.842 (9)C16—H161.0000
O1W—H120.842 (9)C17—C181.543 (3)
C1—C21.567 (3)C17—H17A0.9900
C1—H1A0.9800C17—H17B0.9900
C1—H1B0.9800C18—C191.526 (3)
C1—H1C0.9800C18—C201.571 (3)
C2—C31.490 (3)C18—H181.0000
C2—C71.517 (3)C19—H19A0.9800
C2—C111.583 (2)C19—H19B0.9800
C3—C41.333 (3)C19—H19C0.9800
C3—H30.9500C20—C211.529 (3)
C4—C51.459 (3)C21—C221.521 (3)
C4—H40.9500C22—H22A0.9900
C5—C61.467 (3)C22—H22B0.9900
C6—C71.333 (3)C23—C241.503 (3)
C6—H60.9500C24—C251.504 (3)
C7—C81.498 (3)C24—H24A0.9900
C8—C91.537 (3)C24—H24B0.9900
C8—H8A0.9900C25—H25A0.9800
C8—H8B0.9900C25—H25B0.9800
C9—C101.529 (3)C25—H25C0.9800
C9—H9A0.9900C26—C271.496 (3)
C9—H9B0.9900C27—C281.493 (3)
C10—C161.529 (3)C27—H27A0.9900
C10—C111.541 (3)C27—H27B0.9900
C10—H101.0000C28—H28A0.9800
C11—C121.550 (3)C28—H28B0.9800
C12—C131.546 (3)C28—H28C0.9800
C12—O2—H2107.7 (15)C14—C15—H15B109.5
C23—O4—C22115.02 (15)H15A—C15—H15B109.5
C26—O6—C20120.91 (14)C14—C15—H15C109.5
H11—O1W—H12108.1 (14)H15A—C15—H15C109.5
C2—C1—H1A109.5H15B—C15—H15C109.5
C2—C1—H1B109.5C17—C16—C10119.09 (16)
H1A—C1—H1B109.5C17—C16—C14103.05 (14)
C2—C1—H1C109.5C10—C16—C14113.48 (15)
H1A—C1—H1C109.5C17—C16—H16106.8
H1B—C1—H1C109.5C10—C16—H16106.8
C3—C2—C7112.70 (16)C14—C16—H16106.8
C3—C2—C1105.68 (17)C16—C17—C18103.28 (15)
C7—C2—C1106.38 (16)C16—C17—H17A111.1
C3—C2—C11111.16 (16)C18—C17—H17A111.1
C7—C2—C11107.50 (16)C16—C17—H17B111.1
C1—C2—C11113.43 (14)C18—C17—H17B111.1
C4—C3—C2124.9 (2)H17A—C17—H17B109.1
C4—C3—H3117.6C19—C18—C17112.71 (16)
C2—C3—H3117.6C19—C18—C20118.36 (16)
C3—C4—C5120.9 (2)C17—C18—C20105.77 (15)
C3—C4—H4119.5C19—C18—H18106.4
C5—C4—H4119.5C17—C18—H18106.4
O1—C5—C4122.3 (2)C20—C18—H18106.4
O1—C5—C6121.3 (2)C18—C19—H19A109.5
C4—C5—C6116.43 (17)C18—C19—H19B109.5
C7—C6—C5123.2 (2)H19A—C19—H19B109.5
C7—C6—H6118.4C18—C19—H19C109.5
C5—C6—H6118.4H19A—C19—H19C109.5
C6—C7—C8122.6 (2)H19B—C19—H19C109.5
C6—C7—C2121.8 (2)O6—C20—C21109.42 (15)
C8—C7—C2115.62 (16)O6—C20—C18108.99 (15)
C7—C8—C9110.72 (17)C21—C20—C18117.93 (15)
C7—C8—H8A109.5O6—C20—C14103.17 (13)
C9—C8—H8A109.5C21—C20—C14111.98 (15)
C7—C8—H8B109.5C18—C20—C14104.25 (15)
C9—C8—H8B109.5O3—C21—C22120.75 (17)
H8A—C8—H8B108.1O3—C21—C20121.59 (18)
C10—C9—C8112.12 (17)C22—C21—C20117.53 (16)
C10—C9—H9A109.2O4—C22—C21111.44 (16)
C8—C9—H9A109.2O4—C22—H22A109.3
C10—C9—H9B109.2C21—C22—H22A109.3
C8—C9—H9B109.2O4—C22—H22B109.3
H9A—C9—H9B107.9C21—C22—H22B109.3
C9—C10—C16110.74 (16)H22A—C22—H22B108.0
C9—C10—C11112.43 (15)O5—C23—O4122.26 (18)
C16—C10—C11110.33 (16)O5—C23—C24125.7 (2)
C9—C10—H10107.7O4—C23—C24112.03 (17)
C16—C10—H10107.7C23—C24—C25113.52 (17)
C11—C10—H10107.7C23—C24—H24A108.9
C10—C11—C12113.44 (14)C25—C24—H24A108.9
C10—C11—C2111.36 (15)C23—C24—H24B108.9
C12—C11—C2115.16 (16)C25—C24—H24B108.9
C10—C11—Br1108.15 (13)H24A—C24—H24B107.7
C12—C11—Br1102.88 (12)C24—C25—H25A109.5
C2—C11—Br1104.87 (11)C24—C25—H25B109.5
O2—C12—C13112.67 (15)H25A—C25—H25B109.5
O2—C12—C11107.10 (15)C24—C25—H25C109.5
C13—C12—C11113.39 (16)H25A—C25—H25C109.5
O2—C12—H12A107.8H25B—C25—H25C109.5
C13—C12—H12A107.8O7—C26—O6122.58 (18)
C11—C12—H12A107.8O7—C26—C27126.86 (18)
C14—C13—C12112.99 (16)O6—C26—C27110.56 (17)
C14—C13—H13A109.0C28—C27—C26114.81 (19)
C12—C13—H13A109.0C28—C27—H27A108.6
C14—C13—H13B109.0C26—C27—H27A108.6
C12—C13—H13B109.0C28—C27—H27B108.6
H13A—C13—H13B107.8C26—C27—H27B108.6
C16—C14—C13108.75 (13)H27A—C27—H27B107.5
C16—C14—C15112.57 (15)C27—C28—H28A109.5
C13—C14—C15111.15 (16)C27—C28—H28B109.5
C16—C14—C2099.10 (14)H28A—C28—H28B109.5
C13—C14—C20115.80 (15)C27—C28—H28C109.5
C15—C14—C20108.99 (13)H28A—C28—H28C109.5
C14—C15—H15A109.5H28B—C28—H28C109.5
C7—C2—C3—C40.7 (3)C11—C10—C16—C17178.77 (15)
C1—C2—C3—C4115.0 (2)C9—C10—C16—C14177.67 (15)
C11—C2—C3—C4121.5 (2)C11—C10—C16—C1457.2 (2)
C2—C3—C4—C52.9 (3)C13—C14—C16—C17170.68 (15)
C3—C4—C5—O1176.2 (2)C15—C14—C16—C1765.69 (18)
C3—C4—C5—C64.1 (3)C20—C14—C16—C1749.36 (16)
O1—C5—C6—C7176.8 (2)C13—C14—C16—C1059.2 (2)
C4—C5—C6—C73.5 (3)C15—C14—C16—C1064.46 (19)
C5—C6—C7—C8178.16 (18)C20—C14—C16—C10179.52 (15)
C5—C6—C7—C21.6 (3)C10—C16—C17—C18170.04 (16)
C3—C2—C7—C60.0 (3)C14—C16—C17—C1843.38 (18)
C1—C2—C7—C6115.3 (2)C16—C17—C18—C19149.83 (17)
C11—C2—C7—C6122.9 (2)C16—C17—C18—C2019.04 (19)
C3—C2—C7—C8179.71 (17)C26—O6—C20—C2169.4 (2)
C1—C2—C7—C864.9 (2)C26—O6—C20—C1860.9 (2)
C11—C2—C7—C856.9 (2)C26—O6—C20—C14171.26 (16)
C6—C7—C8—C9123.4 (2)C19—C18—C20—O6134.07 (17)
C2—C7—C8—C956.3 (2)C17—C18—C20—O698.47 (16)
C7—C8—C9—C1051.6 (2)C19—C18—C20—C218.6 (3)
C8—C9—C10—C16176.37 (16)C17—C18—C20—C21136.05 (17)
C8—C9—C10—C1152.4 (2)C19—C18—C20—C14116.29 (18)
C9—C10—C11—C12173.84 (16)C17—C18—C20—C1411.17 (18)
C16—C10—C11—C1249.7 (2)C16—C14—C20—O677.41 (15)
C9—C10—C11—C254.3 (2)C13—C14—C20—O638.62 (19)
C16—C10—C11—C2178.48 (14)C15—C14—C20—O6164.80 (14)
C9—C10—C11—Br160.40 (18)C16—C14—C20—C21165.02 (15)
C16—C10—C11—Br163.76 (16)C13—C14—C20—C2178.94 (19)
C3—C2—C11—C10177.98 (16)C15—C14—C20—C2147.2 (2)
C7—C2—C11—C1054.21 (19)C16—C14—C20—C1836.43 (16)
C1—C2—C11—C1063.1 (2)C13—C14—C20—C18152.47 (14)
C3—C2—C11—C1251.1 (2)C15—C14—C20—C1881.36 (18)
C7—C2—C11—C12174.83 (15)O6—C20—C21—O3168.22 (17)
C1—C2—C11—C1267.9 (2)C18—C20—C21—O342.9 (3)
C3—C2—C11—Br161.25 (18)C14—C20—C21—O378.0 (2)
C7—C2—C11—Br162.53 (16)O6—C20—C21—C2215.8 (2)
C1—C2—C11—Br1179.84 (14)C18—C20—C21—C22141.12 (18)
C10—C11—C12—O278.15 (19)C14—C20—C21—C2297.9 (2)
C2—C11—C12—O251.8 (2)C23—O4—C22—C2175.7 (2)
Br1—C11—C12—O2165.26 (11)O3—C21—C22—O413.0 (3)
C10—C11—C12—C1346.8 (2)C20—C21—C22—O4162.93 (17)
C2—C11—C12—C13176.72 (15)C22—O4—C23—O50.3 (3)
Br1—C11—C12—C1369.82 (16)C22—O4—C23—C24179.85 (17)
O2—C12—C13—C1472.5 (2)O5—C23—C24—C2526.0 (3)
C11—C12—C13—C1449.3 (2)O4—C23—C24—C25154.08 (19)
C12—C13—C14—C1654.1 (2)C20—O6—C26—O79.0 (3)
C12—C13—C14—C1570.40 (19)C20—O6—C26—C27171.58 (17)
C12—C13—C14—C20164.53 (15)O7—C26—C27—C283.2 (4)
C9—C10—C16—C1756.1 (2)O6—C26—C27—C28176.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1w0.83 (1)1.93 (1)2.759 (2)173 (2)
O1w—H11···O50.84 (1)2.06 (1)2.859 (2)159 (3)
O1w—H12···O7i0.84 (1)2.03 (1)2.854 (2)168 (2)
Symmetry code: (i) x+3/2, y+2, z1/2.

Experimental details

Crystal data
Chemical formulaC28H37BrO7·H2O
Mr583.50
Crystal system, space groupOrthorhombic, P212121
Temperature (K)140
a, b, c (Å)11.9565 (2), 14.1329 (2), 16.1648 (3)
V3)2731.53 (8)
Z4
Radiation typeMo Kα
µ (mm1)1.55
Crystal size (mm)0.40 × 0.08 × 0.08
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.611, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
18917, 6226, 5575
Rint0.028
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.026, 0.055, 0.96
No. of reflections6226
No. of parameters351
No. of restraints4
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.39, 0.25
Absolute structureFlack (1983), 2717 Friedel pairs
Absolute structure parameter0.001 (5)

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···O1w0.83 (1)1.93 (1)2.759 (2)173 (2)
O1w—H11···O50.84 (1)2.06 (1)2.859 (2)159 (3)
O1w—H12···O7i0.84 (1)2.03 (1)2.854 (2)168 (2)
Symmetry code: (i) x+3/2, y+2, z1/2.
 

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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