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In the title compound, C18H18Br2O5·H2O, the solvent water mol­ecule is bonded to two O atoms of a crown ether mol­ecule by O—H...O hydrogen bonds. In the crystal structure, mol­ecules of this macrocycle form columns along the [100] crystallographic direction as a result of stacking inter­actions between aromatic rings (centroid–centroid distance 3.5 Å).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807022532/lh2381sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807022532/lh2381Isup2.hkl
Contains datablock I

CCDC reference: 651439

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.053
  • wR factor = 0.156
  • Data-to-parameter ratio = 17.9

checkCIF/PLATON results

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Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.80 mm PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 500 Ang. PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7 PLAT355_ALERT_3_C Long O-H Bond (0.82A) O1S - H1OB ... 1.01 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: All authors made significant contribution in this work. The idea of synthesis belongs to Kamalov and Kotlyar. The synthesis was performed by Grygorash and Pluzhnik-Gladyr. X-ray diffraction experiment was performed by Shishkina. The analysis of diffraction data was performed by Shishkin.

1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Comment top

Crown ethers (CE), containing diphenyl oxide fragment (I, n=1–3), are structural isomers of the corresponding distal ("symmertic", x=y if n=2) and proximal ("asymmetric", x≠y if n=1–3) dibenzoCE (II) (Fig. 3). Products of disubstitution in the aromatic fragment of compounds (I) were not obtained before. As known, dibenzoCE of type (II) in such reactions form only the mixture of cis- and trans-isomers (Hiraoka, 1982; Gokel & Korzeniowski, 1982), which can be very rarely separated. We found out (Kamalov et al., 2003) that bromination of [1.4]dibenzo-15-crown-5 (III) by N-bromosuccinimide leads only to 5,5I-dibromide (IV) (Fig. 4). In the case of other CE (I) under investigation the bromination also takes place selectively. In this paper we report the crystal structure of the compound (IV) monohydrate (Fig. 1), which is formed during treatment of the obtained CE with water. Analysis of the molecular structure of the title compound demonstrates that the O4, O5, O1 and O2 atoms are co-planar within 0.03 Å. The O3 atom is displaced from this plane by 0.76 Å. The O—C—C—O fragments have alternating +sc and -sc conformations (Table 1). The aromatic rings are rotated relative to each other (angle between their mean planes is 65.8 °) due to repulsion between them (there are shortened intramolecular contacts of H5···C7 = 2.62 Å [sum of van der Waals radii is 2.87 Å (Zefirov & Zorky, 1995)], H5···C8 = 2.76 Å, C5···C8 3.24 Å [sum of van der Waals radii is 3.42 Å]). The O1 and O2 atoms are displaced from the plane of aromatic ring (the O1—C7—C12—O2 torsion angle is 8.7 (7) °). In the crystal structure, molecules of compound (IV) form columns along the (0 0 1) crystallographic direction with parallel arrangement of aromatic rings (Fig.2). The distance between neighbouring phenyl rings in columns is ca 3.5 Å, and it allows us to assume the existence of π···π stacking interactions. The macrocycle cavity is capped from one side by water molecule, which is bonded with two oxygen atoms of macrocycle by intermolecular hydrogen bonds (see Table 1). The other side of cavity is capped by a phenyl ring of a symmetry related molecule. A weak intermolecular hydrogen bond C3—H3···O2(x,0.5 - y,1/2 + z) with H···O = 2.42 Å, C—H···O = 163 ° is also present. Some short intermolecular distances are also observed, e.g. Br1···H16b(x - 1,0.5 - y,1/2 + z) = 3.09 Å (3.23 Å), Br2···Br(2(-x,1 - y,2 - z) = 3.73 Å (3.94 Å), Br2···H15b(x - 1,y,1 + z) = 3.08 Å (3.23 Å).

Related literature top

For related literature, see: Gokel & Korzeniowski (1982); Hiraoka (1982); Kamalov et al. (2003); Zefirov & Zorky (1995).

Experimental top

N-Bromosuccinimide (1.9 g, 10.68 mmol) was added to a solution of [1.4]dibenzo-15-crown-5 (1.63 g, 5.15 mmol) in 15 ml CHCl3. The reaction mixture was refluxed for 1 h then cooled and filtered. The residue was washed with 15 ml of CHCl3 and the combined filtrates were evaporated at the lowered pressure until dry. The was residue was washed with water, filtered, dried at the open air to constant weight and crystallized from propanol-2. The yield of compound IV is 83% (2.03 g, white crystals), [m.p. 375–376 K]. Analysis, calculated for C18H18Br2O5: C 45.52, H 3.79, Br 33.68%; found: C 45.60, H 3.83, Br 33.70%. The crystals are soluble in benzene, acetone, dichloromethane, chloroform, dimethyl sulfoxide, dimethyl formamide and other organic solvents. 1H NMR spectrum (Varian VXR-300, in CDCl3, relative to the inner standard Me4Si): Har 7.22–7.20 (2H, dd), J=9.3, J=1.5; 7.06–7.03 (2H, d), J=9.3; 6.87–7.63 (2H, d), J=1.5; CH2CH2O - 4.18–4.15 (4H, m), 3.64–3.61 (4H, m), 3.52 (4H, s). TLC (Silufol UV 254, Kavalier, plates, the visualization was performed under UV light): Rf 0.54 (aceton-n-hexane = 1:1). Transparent colourless crystals of (IV).H2O, suitable for X-ray were obtained by spontaneous evaporation of 95% ethanol solution.

Refinement top

All hydrogen atoms were located in electron density difference maps but included in the refinement in the riding-model approximation with C—H = 0.95–0.99Å and Uiso(H) = 1.2Ueq(C). The H atoms of the water molecule were included in the refinement in their as found positions with Uiso(H) = 1.5Ueq(C). The three largest peaks on the final difference Fourier are 1.12, 0.79 and 1.87Å from C17, C11 and O1s, respectively.

Structure description top

Crown ethers (CE), containing diphenyl oxide fragment (I, n=1–3), are structural isomers of the corresponding distal ("symmertic", x=y if n=2) and proximal ("asymmetric", x≠y if n=1–3) dibenzoCE (II) (Fig. 3). Products of disubstitution in the aromatic fragment of compounds (I) were not obtained before. As known, dibenzoCE of type (II) in such reactions form only the mixture of cis- and trans-isomers (Hiraoka, 1982; Gokel & Korzeniowski, 1982), which can be very rarely separated. We found out (Kamalov et al., 2003) that bromination of [1.4]dibenzo-15-crown-5 (III) by N-bromosuccinimide leads only to 5,5I-dibromide (IV) (Fig. 4). In the case of other CE (I) under investigation the bromination also takes place selectively. In this paper we report the crystal structure of the compound (IV) monohydrate (Fig. 1), which is formed during treatment of the obtained CE with water. Analysis of the molecular structure of the title compound demonstrates that the O4, O5, O1 and O2 atoms are co-planar within 0.03 Å. The O3 atom is displaced from this plane by 0.76 Å. The O—C—C—O fragments have alternating +sc and -sc conformations (Table 1). The aromatic rings are rotated relative to each other (angle between their mean planes is 65.8 °) due to repulsion between them (there are shortened intramolecular contacts of H5···C7 = 2.62 Å [sum of van der Waals radii is 2.87 Å (Zefirov & Zorky, 1995)], H5···C8 = 2.76 Å, C5···C8 3.24 Å [sum of van der Waals radii is 3.42 Å]). The O1 and O2 atoms are displaced from the plane of aromatic ring (the O1—C7—C12—O2 torsion angle is 8.7 (7) °). In the crystal structure, molecules of compound (IV) form columns along the (0 0 1) crystallographic direction with parallel arrangement of aromatic rings (Fig.2). The distance between neighbouring phenyl rings in columns is ca 3.5 Å, and it allows us to assume the existence of π···π stacking interactions. The macrocycle cavity is capped from one side by water molecule, which is bonded with two oxygen atoms of macrocycle by intermolecular hydrogen bonds (see Table 1). The other side of cavity is capped by a phenyl ring of a symmetry related molecule. A weak intermolecular hydrogen bond C3—H3···O2(x,0.5 - y,1/2 + z) with H···O = 2.42 Å, C—H···O = 163 ° is also present. Some short intermolecular distances are also observed, e.g. Br1···H16b(x - 1,0.5 - y,1/2 + z) = 3.09 Å (3.23 Å), Br2···Br(2(-x,1 - y,2 - z) = 3.73 Å (3.94 Å), Br2···H15b(x - 1,y,1 + z) = 3.08 Å (3.23 Å).

For related literature, see: Gokel & Korzeniowski (1982); Hiraoka (1982); Kamalov et al. (2003); Zefirov & Zorky (1995).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with the atomic membering. All atoms are shown with displacement ellipsoids drawn at the 50% probability level. The dashed lines indicate hydrogen bonds.
[Figure 2] Fig. 2. Part of the crystal structure of the title compound.
[Figure 3] Fig. 3. The structures of (I) and (II).
[Figure 4] Fig. 4. The formation of (IV).
2,17-Dibromo-6,7,9,10,12,13- hexahydrodibenzo[b,e][1,4,7,10,13]pentaoxacyclopentadecin monohydrate top
Crystal data top
C18H18Br2O5·H2OF(000) = 984
Mr = 492.16Dx = 1.763 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybcCell parameters from 3187 reflections
a = 10.012 (5) Åθ = 4–35°
b = 26.850 (5) ŵ = 4.41 mm1
c = 7.031 (5) ÅT = 100 K
β = 101.245 (5)°Needle, colourless
V = 1853.8 (16) Å30.80 × 0.10 × 0.10 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur 3
diffractometer
4196 independent reflections
Radiation source: Enhance (Mo) X-ray Source2786 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
Detector resolution: 16.1827 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = 1312
Absorption correction: analytical
(Alcock, 1970)
k = 3420
Tmin = 0.267, Tmax = 0.674l = 97
8042 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: difference Fourier map
wR(F2) = 0.156H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0894P)2]
where P = (Fo2 + 2Fc2)/3
4196 reflections(Δ/σ)max = 0.001
235 parametersΔρmax = 1.56 e Å3
0 restraintsΔρmin = 1.40 e Å3
Crystal data top
C18H18Br2O5·H2OV = 1853.8 (16) Å3
Mr = 492.16Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.012 (5) ŵ = 4.41 mm1
b = 26.850 (5) ÅT = 100 K
c = 7.031 (5) Å0.80 × 0.10 × 0.10 mm
β = 101.245 (5)°
Data collection top
Oxford Diffraction Xcalibur 3
diffractometer
4196 independent reflections
Absorption correction: analytical
(Alcock, 1970)
2786 reflections with I > 2σ(I)
Tmin = 0.267, Tmax = 0.674Rint = 0.049
8042 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.156H-atom parameters constrained
S = 1.03Δρmax = 1.56 e Å3
4196 reflectionsΔρmin = 1.40 e Å3
235 parameters
Special details top

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.17500 (5)0.20334 (2)0.59174 (7)0.02721 (18)
Br20.09743 (5)0.45440 (2)0.88064 (7)0.02732 (18)
O10.4996 (3)0.36064 (14)0.6514 (5)0.0253 (8)
O20.4725 (4)0.41181 (13)0.3243 (5)0.0241 (8)
O30.7321 (3)0.42023 (14)0.2538 (5)0.0214 (7)
O40.8663 (3)0.33494 (13)0.4418 (5)0.0218 (8)
O50.7177 (3)0.30854 (14)0.7383 (5)0.0223 (8)
C10.5977 (5)0.28185 (19)0.7094 (6)0.0172 (10)
C20.5905 (5)0.2310 (2)0.7246 (7)0.0206 (10)
H20.67130.21180.75840.025*
C30.4628 (5)0.20763 (19)0.6897 (6)0.0196 (10)
H30.45650.17250.69980.024*
C40.3470 (5)0.2359 (2)0.6409 (6)0.0199 (10)
C50.3525 (5)0.28774 (19)0.6283 (6)0.0177 (10)
H50.27150.30690.59540.021*
C60.4782 (5)0.31043 (19)0.6646 (6)0.0190 (10)
C70.3927 (5)0.39384 (19)0.6106 (7)0.0194 (10)
C80.3062 (5)0.4028 (2)0.7389 (7)0.0193 (10)
H80.31160.38270.85140.023*
C90.2113 (5)0.4413 (2)0.7021 (7)0.0215 (11)
C100.2026 (5)0.4705 (2)0.5394 (7)0.0223 (11)
H100.13780.49670.51590.027*
C110.2878 (5)0.46175 (18)0.4100 (7)0.0204 (10)
H110.28050.48190.29740.024*
C120.3843 (5)0.42354 (19)0.4431 (7)0.0215 (10)
C130.5051 (5)0.44934 (19)0.1948 (7)0.0213 (11)
H13B0.53510.48030.26700.026*
H13A0.42440.45700.09330.026*
C140.6174 (5)0.4288 (2)0.1053 (7)0.0244 (11)
H14B0.58790.39720.03720.029*
H14A0.64080.45270.00970.029*
C150.8397 (5)0.3949 (2)0.1904 (7)0.0246 (11)
H15B0.88950.41800.11930.029*
H15A0.80320.36720.10260.029*
C160.9332 (5)0.3751 (2)0.3668 (7)0.0249 (11)
H16B1.01910.36340.33230.030*
H16A0.95520.40170.46550.030*
C170.9287 (5)0.3213 (2)0.6340 (7)0.0211 (10)
H17B0.93880.35090.71960.025*
H17A1.02010.30710.63580.025*
C180.8378 (5)0.2831 (2)0.7032 (7)0.0211 (10)
H18B0.81190.25690.60350.025*
H18A0.88640.26710.82390.025*
O1S0.7389 (4)0.42336 (15)0.6775 (5)0.0303 (9)
H1OA0.74010.42530.56210.046*
H1OB0.72130.39070.74090.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0280 (3)0.0202 (3)0.0331 (3)0.0049 (2)0.0050 (2)0.0027 (2)
Br20.0275 (3)0.0268 (3)0.0303 (3)0.0004 (2)0.0121 (2)0.0046 (2)
O10.0239 (18)0.0122 (18)0.041 (2)0.0017 (15)0.0104 (15)0.0093 (16)
O20.0338 (19)0.0107 (18)0.0316 (19)0.0005 (16)0.0159 (15)0.0015 (15)
O30.0257 (18)0.0184 (19)0.0205 (17)0.0036 (16)0.0059 (13)0.0013 (14)
O40.0285 (18)0.0183 (19)0.0183 (16)0.0032 (16)0.0042 (13)0.0008 (14)
O50.0242 (18)0.0177 (19)0.0265 (17)0.0012 (15)0.0084 (14)0.0010 (15)
C10.021 (2)0.019 (3)0.014 (2)0.002 (2)0.0071 (17)0.0030 (19)
C20.026 (2)0.016 (3)0.021 (2)0.004 (2)0.0082 (19)0.001 (2)
C30.031 (3)0.011 (2)0.018 (2)0.001 (2)0.0091 (19)0.0009 (19)
C40.024 (2)0.018 (3)0.018 (2)0.004 (2)0.0043 (18)0.002 (2)
C50.021 (2)0.016 (3)0.017 (2)0.001 (2)0.0060 (17)0.0037 (19)
C60.030 (3)0.012 (2)0.017 (2)0.004 (2)0.0094 (19)0.0003 (19)
C70.018 (2)0.015 (3)0.025 (2)0.003 (2)0.0042 (18)0.002 (2)
C80.018 (2)0.020 (3)0.020 (2)0.001 (2)0.0038 (17)0.002 (2)
C90.024 (3)0.017 (3)0.024 (2)0.004 (2)0.0042 (19)0.005 (2)
C100.024 (2)0.014 (3)0.026 (3)0.001 (2)0.002 (2)0.004 (2)
C110.027 (3)0.008 (2)0.026 (2)0.001 (2)0.005 (2)0.000 (2)
C120.028 (3)0.013 (3)0.024 (2)0.002 (2)0.0075 (19)0.001 (2)
C130.030 (3)0.012 (3)0.021 (2)0.001 (2)0.005 (2)0.003 (2)
C140.033 (3)0.020 (3)0.022 (2)0.003 (2)0.008 (2)0.002 (2)
C150.030 (3)0.020 (3)0.026 (3)0.001 (2)0.013 (2)0.001 (2)
C160.024 (2)0.024 (3)0.027 (3)0.000 (2)0.007 (2)0.002 (2)
C170.023 (2)0.019 (3)0.022 (2)0.003 (2)0.0047 (19)0.002 (2)
C180.021 (2)0.021 (3)0.024 (2)0.007 (2)0.0097 (18)0.002 (2)
O1S0.047 (2)0.019 (2)0.0265 (19)0.0048 (18)0.0104 (16)0.0002 (16)
Geometric parameters (Å, º) top
Br1—C41.901 (5)C8—H80.9500
Br2—C91.886 (5)C9—C101.376 (7)
O1—C61.371 (6)C10—C111.383 (7)
O1—C71.379 (6)C10—H100.9500
O2—C121.365 (6)C11—C121.398 (7)
O2—C131.438 (6)C11—H110.9500
O3—C141.412 (6)C13—C141.498 (7)
O3—C151.418 (6)C13—H13B0.9900
O4—C171.421 (6)C13—H13A0.9900
O4—C161.424 (6)C14—H14B0.9900
O5—C11.380 (6)C14—H14A0.9900
O5—C181.446 (6)C15—C161.497 (7)
C1—C21.373 (7)C15—H15B0.9900
C1—C61.404 (7)C15—H15A0.9900
C2—C31.402 (7)C16—H16B0.9900
C2—H20.9500C16—H16A0.9900
C3—C41.371 (7)C17—C181.514 (7)
C3—H30.9500C17—H17B0.9900
C4—C51.398 (7)C17—H17A0.9900
C5—C61.376 (7)C18—H18B0.9900
C5—H50.9500C18—H18A0.9900
C7—C81.388 (6)O1S—H1OA0.8159
C7—C121.411 (7)O1S—H1OB1.0151
C8—C91.393 (7)
C6—O1—C7121.6 (4)O2—C12—C7116.1 (4)
C12—O2—C13118.7 (4)C11—C12—C7118.7 (5)
C14—O3—C15113.8 (4)O2—C13—C14106.8 (4)
C17—O4—C16113.3 (4)O2—C13—H13B110.4
C1—O5—C18117.3 (4)C14—C13—H13B110.4
C2—C1—O5124.2 (4)O2—C13—H13A110.4
C2—C1—C6120.4 (5)C14—C13—H13A110.4
O5—C1—C6115.4 (5)H13B—C13—H13A108.6
C1—C2—C3119.4 (5)O3—C14—C13108.5 (4)
C1—C2—H2120.3O3—C14—H14B110.0
C3—C2—H2120.3C13—C14—H14B110.0
C4—C3—C2119.6 (5)O3—C14—H14A110.0
C4—C3—H3120.2C13—C14—H14A110.0
C2—C3—H3120.2H14B—C14—H14A108.4
C3—C4—C5121.7 (5)O3—C15—C16107.5 (4)
C3—C4—Br1118.9 (4)O3—C15—H15B110.2
C5—C4—Br1119.4 (4)C16—C15—H15B110.2
C6—C5—C4118.4 (5)O3—C15—H15A110.2
C6—C5—H5120.8C16—C15—H15A110.2
C4—C5—H5120.8H15B—C15—H15A108.5
O1—C6—C5124.9 (5)O4—C16—C15108.2 (4)
O1—C6—C1114.5 (4)O4—C16—H16B110.1
C5—C6—C1120.5 (5)C15—C16—H16B110.1
O1—C7—C8122.3 (4)O4—C16—H16A110.1
O1—C7—C12117.1 (4)C15—C16—H16A110.1
C8—C7—C12120.1 (5)H16B—C16—H16A108.4
C7—C8—C9119.8 (4)O4—C17—C18107.4 (4)
C7—C8—H8120.1O4—C17—H17B110.2
C9—C8—H8120.1C18—C17—H17B110.2
C10—C9—C8120.5 (5)O4—C17—H17A110.2
C10—C9—Br2119.9 (4)C18—C17—H17A110.2
C8—C9—Br2119.6 (4)H17B—C17—H17A108.5
C9—C10—C11120.2 (5)O5—C18—C17107.8 (4)
C9—C10—H10119.9O5—C18—H18B110.1
C11—C10—H10119.9C17—C18—H18B110.1
C10—C11—C12120.7 (5)O5—C18—H18A110.1
C10—C11—H11119.7C17—C18—H18A110.1
C12—C11—H11119.7H18B—C18—H18A108.5
O2—C12—C11125.2 (4)H1OA—O1S—H1OB121.9
C18—O5—C1—C226.5 (6)C7—C8—C9—Br2178.3 (4)
C18—O5—C1—C6154.4 (4)C8—C9—C10—C110.3 (7)
O5—C1—C2—C3179.2 (4)Br2—C9—C10—C11178.6 (4)
C6—C1—C2—C31.7 (7)C9—C10—C11—C120.5 (7)
C1—C2—C3—C40.0 (7)C13—O2—C12—C1122.8 (7)
C2—C3—C4—C51.2 (7)C13—O2—C12—C7157.8 (4)
C2—C3—C4—Br1179.4 (3)C10—C11—C12—O2179.7 (5)
C3—C4—C5—C60.6 (7)C10—C11—C12—C70.4 (7)
Br1—C4—C5—C6180.0 (3)O1—C7—C12—O28.4 (7)
C7—O1—C6—C54.1 (7)C8—C7—C12—O2179.4 (4)
C7—O1—C6—C1179.2 (4)O1—C7—C12—C11172.2 (4)
C4—C5—C6—O1177.7 (4)C8—C7—C12—C110.0 (7)
C4—C5—C6—C11.3 (6)C12—O2—C13—C14172.0 (4)
C2—C1—C6—O1179.2 (4)C15—O3—C14—C13172.5 (4)
O5—C1—C6—O11.7 (6)O2—C13—C14—O362.3 (5)
C2—C1—C6—C52.4 (7)C14—O3—C15—C16163.2 (4)
O5—C1—C6—C5178.5 (4)C17—O4—C16—C15165.0 (4)
C6—O1—C7—C867.1 (6)O3—C15—C16—O471.5 (5)
C6—O1—C7—C12120.8 (5)C16—O4—C17—C18173.1 (4)
O1—C7—C8—C9171.6 (5)C1—O5—C18—C17149.0 (4)
C12—C7—C8—C90.2 (7)O4—C17—C18—O572.2 (5)
C7—C8—C9—C100.1 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1S—H1OA···O30.822.162.968 (5)172
O1S—H1OB···O51.022.213.125 (5)150

Experimental details

Crystal data
Chemical formulaC18H18Br2O5·H2O
Mr492.16
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)10.012 (5), 26.850 (5), 7.031 (5)
β (°) 101.245 (5)
V3)1853.8 (16)
Z4
Radiation typeMo Kα
µ (mm1)4.41
Crystal size (mm)0.80 × 0.10 × 0.10
Data collection
DiffractometerOxford Diffraction Xcalibur 3
Absorption correctionAnalytical
(Alcock, 1970)
Tmin, Tmax0.267, 0.674
No. of measured, independent and
observed [I > 2σ(I)] reflections
8042, 4196, 2786
Rint0.049
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.156, 1.03
No. of reflections4196
No. of parameters235
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.56, 1.40

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), CrysAlis RED, SHELXTL (Sheldrick, 1998), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1S—H1OA···O30.822.162.968 (5)172.2
O1S—H1OB···O51.022.213.125 (5)149.9
 

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