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The title compound {systematic name: 7,11,15,28-tetra­kis­(bromo­meth­yl)-1,21,23,25-tetra­pentyl-2,20:3,19-dimetheno-1H,21H,23H,25H-bis­[1,3]dioxocino[5,4-i:5',4'-i']benzo[1,2-d:5,4-d']bis­[1,3]benzodioxocine 0.415-hydrate}, C56H68Br4O8·0.415H2O, has been previously synthesized and reported; however, its crystal structure has hitherto not been elucidated. The structure is the first reported example of a resorcin[4]arene cavitand bearing bromo­methyl functional groups at the rim of the mol­ecule. The inclusion of Br atoms makes the compound useful as a precursor to a number of synthetically more complex cavitand host mol­ecules.. This is also true of the pentyl `feet' of the title compound. Two pentyl groups are disordered over two positions; the site occupancy factors are ca. 0.68 and 0.32.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807050106/hg2300sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807050106/hg2300Isup2.hkl
Contains datablock I

CCDC reference: 662146

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.006 Å
  • H-atom completeness 99%
  • Disorder in main residue
  • R factor = 0.052
  • wR factor = 0.187
  • Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT220_ALERT_2_A Large Non-Solvent C Ueq(max)/Ueq(min) ... 6.05 Ratio
Author Response: Explained in the text of the _publ_section_exptl_refinement section.
PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       6.78 Ratio
Author Response: Explained in the text of the _publ_section_exptl_refinement section.

Alert level B PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) ....... 4
Alert level C CHEMW01_ALERT_1_C The difference between the given and expected weight for compound is greater 1 mass unit. Check that all hydrogen atoms have been taken into account. PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C54 PLAT301_ALERT_3_C Main Residue Disorder ......................... 9.00 Perc. PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 42.00 Perc. PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) ..... <O1W PLAT413_ALERT_2_C Short Inter XH3 .. XHn H46C .. H56D .. 2.13 Ang.
Alert level G FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C56 H68.83 Br4 O8.41 Atom count from the _atom_site data: C56 H68 Br4 O8.415 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional? From the CIF: _cell_formula_units_Z 2 From the CIF: _chemical_formula_sum C56 H68.83 Br4 O8.41 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 112.00 112.00 0.00 H 137.66 136.00 1.66 Br 8.00 8.00 0.00 O 16.82 16.83 -0.01 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 102
2 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 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

Comment top

The title compound, (II, Scheme 1), has been previously prepared by Boerrigter et al. (1997), as the result of a free radical bromination of (I) using N-bromosuccinimide and the radical initiator, AIBN. The synthesis of (II) in this study, however, followed the synthetic conditions as set out by Sorrell & Pigge (1993), which used benzoyl peroxide as the radical initiator. Interestingly, this is despite observations by Boerrigter et al. that this protocol did not afford the desired product. Indeed, the conditions of Sorrell & Pigge, in conjunction with the use of white light, yielded 76% of pure (II).

In the title compound the [4]arene moiety is a cyclic tetramer. The labelling scheme for one of the monomers, shown in Fig.1, extends over the whole molecule.

The asymmetric unit of (II) is shown in Fig. 2. The bond lengths and bond angles all fall within the normal ranges and are not discussed further. The four bromine atoms which appear at the upper rim of the molecule are orientated such that all four face inwards towards the molecular cavity. Interestingly, (II) appears with a water molecule of partial (0.42) occupancy inside the molecular cavity. This is despite the hydrophobic nature of the cavity. Such partial occupancy has been reported in related structures; for examples see Tunstad et al., (1989) and Cram et al.,(1988).

The bromine atoms give rise to interesting packing arrangements in the crystal structure of (II). As shown in Fig. 3, the individual resorcin[4]arene cavitand molecules pack such that the bromine atoms are in close contact with the corresponding bromine atoms of a neighbouring molecule. This results in alternate layers of bromine atoms, in between the cavities and the 'feet' (pentyl groups) representing the remainder of the cavitand molecules.

In Fig. 4, the feet of (II) are such that two adjacent pentyl groups are linear, while the remaining two are bent. This is due to the interdigitation of a pair of linear chains from one cavitand molecule, with the corresponding chains of a neighbouring cavitand molecule. This results in insufficient space for the remaining pairs of alkyl groups to extend in a linear fashion.

Related literature top

For related literature, see: Boerrigter et al. (1997); Cram et al. (1988); Sorrell & Pigge (1993); Tunstad et al. (1989).

Experimental top

Methyl cavitand (I) (1.00 g, 1.15 mmol) and N-bromosuccinimide (0.90 g, 5.04 mmol) were added to CCl4 (100 ml). A catalytic amount of benzoyl peroxide was added to the solution, and the solution allowed to reflux overnight under irradiation of white light. The orange solution accompanied by a succinimide precipitate was then allowed to cool to room temperature. The precipitate was filtered off, and the orange filtrate concentrated on a rotary evaporator. The resulting solid was chromatographed on silica gel using a chloroform mobile phase. The fractions that were collected were concentrated on a rotary evaporator, and the orange solid product stirred in methanol overnight. The solution was then filtered, and the purified product dried overnight to yield the title compound as a dark orange powder. (1.03 g, 76%), mp 553–555 K. 1H NMR [CDCl3, 300 MHz]: δ = 0.89 (t, 12 H, CH3), 1.28 - 1.50 (m, 24 H, (CH2)3), 2.15 - 2.22 (m, 8 H, CH2), 4.40 (s, 8 H, CH2Br), 4.55 (d, 4 H, inner of OCH2O), 4.76 (t, 4 H, CH(CH2)4CH3), 6.02 (d, 4 H, outer of OCH2O), 7.11 (s, 4 H, Ar H). 13C NMR [CDCl3, 75 MHz]: δ = 153.55, 138.13, 124.55, 121.18, 98.17, 36.87, 32.68, 31.98, 30.08, 27.55, 22.67, 14.10.

Crystals suitable for X-ray crystallography were grown by slow liquid diffusion of methanol into a solution of the title compound in 1:1 e thyl acetate:hexane.

Refinement top

Hydrogen atoms, first located in the difference map, were positioned geometrically and allowed to ride on their respective parent atoms, with C—H bond lengths of 1.00 (CH), 0.99 (CH2), or 0.98 (CH3). They were then refined with a riding model with Uiso(H) = 1.5Ueq(CH3) and Uiso(H) = 1.2Ueq(X) for X = CH or CH2. Two of the four pentyl groups are disordered. These were refined over two positions using SIMU, SADI and DELU restraints with the final occupancies being 0.681 (5) for atoms C49—C51, C53—C56 and 0.319 (5) for atoms C49A—C51A, C53A—C56A. In addition, atoms C53—C56 and C53A—C56A were refined isotropically as they did not refine well when refined anisotropically. This is likely due to the presence of further structural disorder which is not fully accounted for by the current disorder model. The atom O1W was introduced into the structural model to account for an electron density feature of approximately 1.4 e/Å3. Its coordinates and sof were refined with its Uiso fixed. This feature is interpreted as the O atom of a water molecule but its low occupancy factor [0.415] has prevented discovery of the associated H atoms which are, therefore, absent from the structural model.

Structure description top

The title compound, (II, Scheme 1), has been previously prepared by Boerrigter et al. (1997), as the result of a free radical bromination of (I) using N-bromosuccinimide and the radical initiator, AIBN. The synthesis of (II) in this study, however, followed the synthetic conditions as set out by Sorrell & Pigge (1993), which used benzoyl peroxide as the radical initiator. Interestingly, this is despite observations by Boerrigter et al. that this protocol did not afford the desired product. Indeed, the conditions of Sorrell & Pigge, in conjunction with the use of white light, yielded 76% of pure (II).

In the title compound the [4]arene moiety is a cyclic tetramer. The labelling scheme for one of the monomers, shown in Fig.1, extends over the whole molecule.

The asymmetric unit of (II) is shown in Fig. 2. The bond lengths and bond angles all fall within the normal ranges and are not discussed further. The four bromine atoms which appear at the upper rim of the molecule are orientated such that all four face inwards towards the molecular cavity. Interestingly, (II) appears with a water molecule of partial (0.42) occupancy inside the molecular cavity. This is despite the hydrophobic nature of the cavity. Such partial occupancy has been reported in related structures; for examples see Tunstad et al., (1989) and Cram et al.,(1988).

The bromine atoms give rise to interesting packing arrangements in the crystal structure of (II). As shown in Fig. 3, the individual resorcin[4]arene cavitand molecules pack such that the bromine atoms are in close contact with the corresponding bromine atoms of a neighbouring molecule. This results in alternate layers of bromine atoms, in between the cavities and the 'feet' (pentyl groups) representing the remainder of the cavitand molecules.

In Fig. 4, the feet of (II) are such that two adjacent pentyl groups are linear, while the remaining two are bent. This is due to the interdigitation of a pair of linear chains from one cavitand molecule, with the corresponding chains of a neighbouring cavitand molecule. This results in insufficient space for the remaining pairs of alkyl groups to extend in a linear fashion.

For related literature, see: Boerrigter et al. (1997); Cram et al. (1988); Sorrell & Pigge (1993); Tunstad et al. (1989).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-NT (Bruker, 2005); data reduction: SAINT-NT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Bruker, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Version 1.4.2; Bruno et al., 2002); software used to prepare material for publication: SHELXTL (Bruker, 1999).

Figures top
[Figure 1] Fig. 1. A view of one component of the cyclic tetramer. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as spheres of arbitrary radii. Dashed bonds indicate links to the neighbouring monomer units. Selected atoms are labelled.
[Figure 2] Fig. 2. The asymmetric unit of (II). Displacement ellipsoids are drawn at the 50% probability level and H atoms, where shown, are drawn as spheres of arbitrary radii. Selected atoms are labelled. The water molecule of partial occupancy is clearly evident, present in the molecular cavity.
[Figure 3] Fig. 3. Packing of the individual cavitand units, showing the close contact between resorcin[4]arene bromine atoms, resulting in layers of bromine atoms in between resorcin[4]arene units.
[Figure 4] Fig. 4. The relative orientation of the feet of (II) in terms of neighbouring resorcin[4]arene units. Displacement ellipsoids are drawn at the 50% probability. The interdigitation of the feet is clearly shown. Hydrogen atoms and the water molecule in each unit have been omitted.
[Figure 5] Fig. 5. The formation of the title compound.
7,11,15,28-tetrakis(bromomethyl)-1,21,23,25-tetrapentyl-2,20:3,19-dimetheno- 1H,21H,23H,25H-bis[1,3]dioxocino[5,4 - i:5',4'-i']benzo[1,2 - d:5,4 - d']bis[1,3] benzodioxocine stereoisomer top
Crystal data top
C56H68Br4O8·0.415H2OZ = 2
Mr = 1197.75F(000) = 1224.3
Triclinic, P1Dx = 1.457 Mg m3
Dm = 1.454 Mg m3
Dm measured by not measured
Hall symbol: -P 1Melting point: 553 K
a = 11.5151 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.9323 (2) ÅCell parameters from 7203 reflections
c = 22.7986 (5) Åθ = 2.3–28.2°
α = 93.655 (1)°µ = 3.00 mm1
β = 92.921 (1)°T = 173 K
γ = 118.676 (1)°Block, colourless
V = 2730.83 (9) Å30.41 × 0.30 × 0.29 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
10730 independent reflections
Radiation source: fine-focus sealed tube7721 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
φ and ω scansθmax = 26.0°, θmin = 0.9°
Absorption correction: integration
[face-indexed absorption corrections carried out with XPREP (Bruker, 2005)]
h = 1414
Tmin = 0.373, Tmax = 0.477k = 1414
42983 measured reflectionsl = 2828
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.187H-atom parameters constrained
S = 1.12 w = 1/[σ2(Fo2) + (0.113P)2 + 1.1716P]
where P = (Fo2 + 2Fc2)/3
10730 reflections(Δ/σ)max = 0.001
649 parametersΔρmax = 1.41 e Å3
102 restraintsΔρmin = 1.41 e Å3
Crystal data top
C56H68Br4O8·0.415H2Oγ = 118.676 (1)°
Mr = 1197.75V = 2730.83 (9) Å3
Triclinic, P1Z = 2
a = 11.5151 (2) ÅMo Kα radiation
b = 11.9323 (2) ŵ = 3.00 mm1
c = 22.7986 (5) ÅT = 173 K
α = 93.655 (1)°0.41 × 0.30 × 0.29 mm
β = 92.921 (1)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
10730 independent reflections
Absorption correction: integration
[face-indexed absorption corrections carried out with XPREP (Bruker, 2005)]
7721 reflections with I > 2σ(I)
Tmin = 0.373, Tmax = 0.477Rint = 0.044
42983 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.052102 restraints
wR(F2) = 0.187H-atom parameters constrained
S = 1.12Δρmax = 1.41 e Å3
10730 reflectionsΔρmin = 1.41 e Å3
649 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*/UeqOcc. (<1)
C10.2648 (4)0.3135 (4)0.83103 (19)0.0297 (10)
C20.3949 (4)0.4079 (4)0.82396 (18)0.0280 (9)
C30.4596 (4)0.4022 (4)0.77546 (18)0.0271 (9)
C40.3927 (4)0.2972 (4)0.73324 (18)0.0284 (9)
H40.43700.29070.70020.034*
C50.2636 (4)0.2017 (4)0.73754 (18)0.0285 (9)
C60.2009 (4)0.2118 (4)0.78623 (19)0.0294 (9)
C70.1982 (4)0.3215 (5)0.88375 (19)0.0354 (10)
H7A0.10080.27810.87360.042*
H7B0.22860.41260.89720.042*
C80.0440 (4)0.0068 (4)0.8155 (2)0.0342 (10)
H8A0.03460.02200.83830.041*
H8B0.12110.02340.84300.041*
C90.1912 (4)0.0826 (4)0.69345 (18)0.0294 (9)
H90.09400.05370.69330.035*
C100.1518 (4)0.1964 (4)0.77947 (17)0.0253 (9)
C110.1310 (4)0.1024 (4)0.75608 (18)0.0270 (9)
C120.2135 (4)0.0228 (4)0.71655 (17)0.0256 (9)
C130.3202 (4)0.0405 (4)0.70139 (17)0.0239 (8)
H130.37870.01400.67530.029*
C140.3437 (4)0.1343 (4)0.72296 (17)0.0223 (8)
C150.2598 (4)0.2102 (4)0.76253 (17)0.0251 (9)
C160.0631 (4)0.2791 (4)0.82210 (19)0.0335 (10)
H16A0.06170.36290.81900.040*
H16B0.02860.29510.81210.040*
C170.3759 (4)0.2732 (4)0.83114 (19)0.0299 (9)
H17A0.38720.19540.85470.036*
H17B0.34670.34320.85730.036*
C180.4623 (4)0.1500 (4)0.70673 (17)0.0235 (8)
H180.43760.24180.70990.028*
C190.6874 (4)0.0514 (4)0.85005 (18)0.0248 (9)
C200.5878 (4)0.1207 (4)0.80484 (19)0.0254 (9)
C210.5767 (4)0.0697 (4)0.75303 (17)0.0208 (8)
C220.6708 (4)0.0567 (4)0.74812 (17)0.0227 (8)
H220.66560.09380.71310.027*
C230.7723 (4)0.1315 (4)0.79198 (17)0.0217 (8)
C240.7765 (4)0.0762 (4)0.84305 (17)0.0231 (8)
C250.6987 (5)0.1108 (4)0.9045 (2)0.0357 (10)
H25A0.79360.07420.91900.043*
H25B0.66140.20440.89490.043*
C260.8615 (4)0.2342 (4)0.92645 (18)0.0301 (10)
H26A0.89730.23510.96700.036*
H26B0.76560.20610.92720.036*
C270.8734 (4)0.2700 (4)0.78705 (17)0.0232 (8)
H270.95460.28800.81280.028*
C280.8035 (4)0.4716 (4)0.90174 (17)0.0238 (9)
C290.8498 (4)0.3950 (4)0.87391 (17)0.0228 (8)
C300.8234 (4)0.3565 (4)0.81336 (17)0.0220 (8)
C310.7456 (4)0.3949 (4)0.78090 (17)0.0236 (8)
H310.72650.36940.73970.028*
C320.6944 (4)0.4697 (4)0.80646 (18)0.0250 (9)
C330.7244 (4)0.5066 (4)0.86678 (17)0.0240 (8)
C340.8352 (4)0.5136 (4)0.96568 (18)0.0286 (9)
H34A0.83440.59570.97400.034*
H34B0.92510.52770.97830.034*
C350.5449 (4)0.5140 (4)0.91094 (18)0.0279 (9)
H35A0.52290.42500.91740.034*
H35B0.53830.55620.94850.034*
C360.6030 (4)0.5056 (4)0.77138 (19)0.0305 (10)
H360.61340.58650.79240.037*
C370.2275 (5)0.1072 (5)0.62994 (18)0.0360 (11)
H37A0.32280.13310.62840.043*
H37B0.21440.17930.61850.043*
C380.1437 (5)0.0115 (5)0.58520 (18)0.0424 (12)
H38A0.14880.08610.59910.051*
H38B0.04960.03150.58350.051*
C390.1889 (5)0.0076 (5)0.52436 (18)0.0475 (13)
H39A0.19330.08780.51250.057*
H39B0.28000.01870.52550.057*
C400.1015 (6)0.1002 (6)0.47847 (19)0.0566 (15)
H40A0.01020.11200.47730.068*
H40B0.09780.18050.48990.068*
C410.1496 (7)0.0772 (7)0.4167 (2)0.080 (2)
H41A0.16020.00550.40640.120*
H41B0.08420.14620.38790.120*
H41C0.23520.07620.41630.120*
C420.4991 (4)0.1216 (4)0.64416 (17)0.0279 (9)
H42A0.58160.12620.63890.033*
H42B0.51830.03270.63910.033*
C430.3914 (4)0.2131 (5)0.59580 (19)0.0372 (11)
H43A0.36690.30260.60250.045*
H43B0.31120.20330.59880.045*
C440.4348 (5)0.1893 (5)0.5340 (2)0.0407 (11)
H44A0.45970.09940.52790.049*
H44B0.51570.19810.53160.049*
C450.3352 (6)0.2749 (6)0.4848 (2)0.0535 (14)
H45A0.25460.26530.48630.064*
H45B0.30940.36510.49060.064*
C460.3868 (6)0.2465 (6)0.4223 (2)0.0617 (16)
H46A0.41290.15730.41620.093*
H46B0.31600.30420.39200.093*
H46C0.46370.26040.41970.093*
C470.9170 (4)0.2961 (4)0.72461 (18)0.0292 (9)
H47A0.93830.22940.70900.035*
H47B0.84250.29010.69850.035*
C481.0383 (5)0.4283 (5)0.7235 (2)0.0488 (14)
H48A1.01070.49410.73200.059*
H48B1.10500.44000.75590.059*
C491.1046 (14)0.4535 (19)0.6669 (4)0.064 (2)0.681 (5)
H49A1.18830.53630.67350.077*0.681 (5)
H49B1.12830.38540.65720.077*0.681 (5)
C501.0233 (9)0.4583 (9)0.6152 (4)0.076 (2)0.681 (5)
H50A1.07350.47330.58000.091*0.681 (5)
H50B0.94050.37500.60710.091*0.681 (5)
C510.9896 (11)0.5626 (10)0.6269 (5)0.090 (3)0.681 (5)
H51A0.93740.56550.59230.135*0.681 (5)
H51B1.07160.64500.63510.135*0.681 (5)
H51C0.93750.54620.66110.135*0.681 (5)
C49A1.081 (4)0.462 (4)0.6627 (9)0.068 (3)0.319 (5)
H49C1.00120.42840.63400.082*0.319 (5)
H49D1.13070.55650.66260.082*0.319 (5)
C50A1.167 (2)0.4054 (19)0.6450 (8)0.070 (3)0.319 (5)
H50C1.24770.44680.67300.084*0.319 (5)
H50D1.11870.31370.65210.084*0.319 (5)
C51A1.211 (2)0.411 (2)0.5848 (8)0.088 (5)0.319 (5)
H51D1.19860.32600.57020.132*0.319 (5)
H51E1.30550.47430.58620.132*0.319 (5)
H51F1.15890.43460.55830.132*0.319 (5)
C520.6385 (5)0.5344 (5)0.7090 (2)0.0457 (12)
H52A0.73630.58790.71010.055*0.681 (5)
H52B0.61330.45240.68510.055*0.681 (5)
H52C0.65980.46830.69240.055*0.319 (5)
H52D0.55800.52220.68540.055*0.319 (5)
C530.5770 (9)0.5997 (9)0.6787 (3)0.067 (2)*0.681 (5)
H53A0.62360.69100.69510.080*0.681 (5)
H53B0.48390.56250.68880.080*0.681 (5)
C540.5754 (8)0.5953 (13)0.6128 (4)0.115 (3)*0.681 (5)
H54A0.53350.50440.59610.138*0.681 (5)
H54B0.51930.63140.59800.138*0.681 (5)
C550.7097 (9)0.6669 (14)0.5908 (4)0.124 (3)*0.681 (5)
H55A0.77010.64000.61020.149*0.681 (5)
H55B0.74620.75990.60230.149*0.681 (5)
C560.7070 (13)0.6444 (14)0.5237 (4)0.122 (4)*0.681 (5)
H56A0.79720.69360.51180.183*0.681 (5)
H56B0.64890.67240.50430.183*0.681 (5)
H56C0.67330.55280.51220.183*0.681 (5)
C53A0.7517 (16)0.6654 (12)0.7093 (7)0.072 (5)*0.319 (5)
H53C0.83210.66660.72770.086*0.319 (5)
H53D0.73390.72480.73470.086*0.319 (5)
C54A0.781 (2)0.7159 (16)0.6503 (7)0.103 (4)*0.319 (5)
H54C0.71860.74690.63870.123*0.319 (5)
H54D0.87220.79030.65390.123*0.319 (5)
C55A0.772 (2)0.620 (3)0.6022 (8)0.120 (4)*0.319 (5)
H55C0.79290.55680.61970.144*0.319 (5)
H55D0.83970.66430.57460.144*0.319 (5)
C56A0.635 (2)0.548 (3)0.5675 (11)0.116 (5)*0.319 (5)
H56D0.60490.45530.56370.174*0.319 (5)
H56E0.64000.57740.52820.174*0.319 (5)
H56F0.57140.56390.58860.174*0.319 (5)
O10.0691 (3)0.1223 (3)0.79143 (14)0.0344 (7)
O20.0211 (3)0.0925 (3)0.77090 (13)0.0326 (7)
O30.2756 (3)0.3082 (3)0.78403 (13)0.0279 (6)
O40.4997 (3)0.2486 (3)0.81165 (13)0.0291 (7)
O50.8766 (3)0.1446 (3)0.88846 (12)0.0265 (6)
O60.9272 (3)0.3609 (3)0.90898 (12)0.0256 (6)
O70.6788 (3)0.5819 (3)0.89468 (12)0.0278 (6)
O80.4525 (3)0.5112 (3)0.86706 (13)0.0312 (7)
Br10.24027 (5)0.23895 (5)0.94766 (2)0.04566 (17)
Br20.12420 (6)0.19738 (6)0.90338 (2)0.05765 (19)
Br30.60254 (6)0.07854 (7)0.96640 (3)0.0609 (2)
Br40.70324 (6)0.38183 (5)1.00981 (2)0.04434 (17)
O1W0.467 (2)0.126 (2)0.8609 (10)0.157 (11)0.415 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.034 (2)0.039 (3)0.029 (2)0.029 (2)0.0028 (18)0.0017 (19)
C20.036 (2)0.030 (2)0.029 (2)0.026 (2)0.0053 (18)0.0003 (18)
C30.039 (2)0.027 (2)0.025 (2)0.024 (2)0.0018 (17)0.0045 (17)
C40.038 (2)0.033 (2)0.022 (2)0.024 (2)0.0010 (17)0.0034 (18)
C50.037 (2)0.036 (2)0.022 (2)0.028 (2)0.0070 (17)0.0017 (18)
C60.029 (2)0.035 (2)0.031 (2)0.023 (2)0.0047 (17)0.0026 (19)
C70.035 (2)0.046 (3)0.034 (2)0.029 (2)0.0023 (19)0.007 (2)
C80.034 (2)0.039 (3)0.031 (2)0.020 (2)0.0049 (19)0.005 (2)
C90.031 (2)0.036 (2)0.024 (2)0.020 (2)0.0050 (17)0.0038 (18)
C100.0234 (19)0.024 (2)0.020 (2)0.0056 (17)0.0008 (15)0.0059 (17)
C110.0211 (19)0.033 (2)0.022 (2)0.0108 (18)0.0010 (16)0.0082 (18)
C120.027 (2)0.029 (2)0.0187 (19)0.0136 (18)0.0043 (16)0.0073 (17)
C130.026 (2)0.023 (2)0.0174 (19)0.0080 (17)0.0008 (15)0.0043 (16)
C140.0183 (18)0.020 (2)0.0205 (19)0.0045 (16)0.0036 (15)0.0089 (16)
C150.0236 (19)0.019 (2)0.025 (2)0.0059 (17)0.0020 (16)0.0062 (17)
C160.032 (2)0.034 (3)0.028 (2)0.010 (2)0.0076 (18)0.0020 (19)
C170.032 (2)0.026 (2)0.031 (2)0.0128 (19)0.0072 (18)0.0066 (19)
C180.0242 (19)0.018 (2)0.026 (2)0.0094 (17)0.0041 (16)0.0031 (16)
C190.029 (2)0.028 (2)0.025 (2)0.0196 (19)0.0029 (16)0.0027 (17)
C200.028 (2)0.017 (2)0.034 (2)0.0124 (17)0.0074 (17)0.0008 (17)
C210.0228 (19)0.019 (2)0.023 (2)0.0127 (17)0.0060 (15)0.0006 (16)
C220.0224 (19)0.023 (2)0.023 (2)0.0109 (17)0.0065 (15)0.0002 (16)
C230.0213 (18)0.024 (2)0.024 (2)0.0138 (17)0.0053 (15)0.0037 (16)
C240.0196 (18)0.026 (2)0.026 (2)0.0137 (17)0.0015 (15)0.0038 (17)
C250.042 (3)0.033 (3)0.038 (3)0.023 (2)0.001 (2)0.005 (2)
C260.036 (2)0.034 (2)0.024 (2)0.021 (2)0.0018 (17)0.0047 (18)
C270.0205 (18)0.022 (2)0.0209 (19)0.0058 (17)0.0032 (15)0.0032 (16)
C280.0202 (18)0.018 (2)0.027 (2)0.0042 (16)0.0033 (16)0.0030 (16)
C290.0177 (18)0.020 (2)0.024 (2)0.0035 (16)0.0043 (15)0.0008 (16)
C300.0192 (18)0.0158 (19)0.0221 (19)0.0015 (16)0.0059 (15)0.0021 (16)
C310.026 (2)0.0158 (19)0.0201 (19)0.0031 (16)0.0049 (15)0.0005 (16)
C320.026 (2)0.0154 (19)0.028 (2)0.0050 (17)0.0048 (16)0.0051 (17)
C330.027 (2)0.0145 (19)0.025 (2)0.0058 (17)0.0052 (16)0.0010 (16)
C340.031 (2)0.023 (2)0.027 (2)0.0111 (18)0.0013 (17)0.0060 (18)
C350.034 (2)0.031 (2)0.024 (2)0.022 (2)0.0033 (17)0.0066 (18)
C360.043 (2)0.022 (2)0.029 (2)0.018 (2)0.0030 (19)0.0043 (18)
C370.044 (3)0.044 (3)0.025 (2)0.026 (2)0.0048 (19)0.001 (2)
C380.049 (3)0.050 (3)0.030 (2)0.028 (3)0.004 (2)0.003 (2)
C390.048 (3)0.060 (4)0.035 (3)0.028 (3)0.003 (2)0.004 (2)
C400.062 (4)0.069 (4)0.039 (3)0.034 (3)0.001 (3)0.011 (3)
C410.097 (5)0.090 (5)0.045 (4)0.041 (4)0.013 (3)0.012 (3)
C420.026 (2)0.026 (2)0.026 (2)0.0086 (18)0.0065 (16)0.0047 (18)
C430.036 (2)0.035 (3)0.029 (2)0.010 (2)0.0023 (19)0.010 (2)
C440.043 (3)0.038 (3)0.034 (3)0.015 (2)0.005 (2)0.007 (2)
C450.062 (3)0.062 (4)0.030 (3)0.028 (3)0.001 (2)0.008 (3)
C460.067 (4)0.072 (4)0.038 (3)0.031 (3)0.007 (3)0.017 (3)
C470.027 (2)0.026 (2)0.025 (2)0.0059 (18)0.0076 (17)0.0041 (18)
C480.049 (3)0.037 (3)0.036 (3)0.001 (2)0.015 (2)0.001 (2)
C490.066 (5)0.051 (4)0.053 (3)0.009 (3)0.028 (3)0.007 (3)
C500.078 (5)0.060 (4)0.053 (3)0.003 (3)0.019 (3)0.011 (3)
C510.083 (6)0.079 (6)0.083 (6)0.020 (5)0.007 (5)0.008 (5)
C49A0.070 (5)0.052 (4)0.056 (4)0.007 (4)0.027 (4)0.008 (4)
C50A0.073 (5)0.052 (5)0.062 (4)0.009 (4)0.029 (4)0.008 (4)
C51A0.098 (9)0.064 (9)0.073 (7)0.013 (7)0.044 (7)0.002 (8)
C520.065 (3)0.036 (3)0.035 (3)0.023 (3)0.007 (2)0.008 (2)
O10.0295 (15)0.0422 (19)0.0380 (17)0.0238 (15)0.0001 (13)0.0039 (15)
O20.0227 (14)0.0355 (17)0.0377 (17)0.0140 (13)0.0029 (12)0.0073 (14)
O30.0290 (15)0.0151 (14)0.0335 (16)0.0062 (12)0.0019 (12)0.0001 (12)
O40.0298 (15)0.0166 (14)0.0405 (17)0.0103 (12)0.0067 (13)0.0052 (13)
O50.0255 (14)0.0285 (16)0.0263 (15)0.0156 (13)0.0057 (11)0.0060 (12)
O60.0222 (13)0.0242 (15)0.0250 (14)0.0081 (12)0.0030 (11)0.0049 (12)
O70.0321 (15)0.0197 (15)0.0307 (16)0.0127 (13)0.0029 (12)0.0051 (12)
O80.0400 (16)0.0283 (16)0.0332 (16)0.0245 (14)0.0036 (13)0.0063 (13)
Br10.0529 (3)0.0517 (3)0.0312 (3)0.0251 (3)0.0032 (2)0.0019 (2)
Br20.0725 (4)0.0600 (4)0.0348 (3)0.0269 (3)0.0122 (3)0.0052 (3)
Br30.0680 (4)0.0706 (4)0.0414 (3)0.0293 (3)0.0125 (3)0.0181 (3)
Br40.0657 (3)0.0457 (3)0.0279 (3)0.0309 (3)0.0146 (2)0.0047 (2)
O1W0.149 (17)0.17 (2)0.19 (2)0.095 (15)0.071 (14)0.038 (15)
Geometric parameters (Å, º) top
C1—C61.402 (6)C37—H37A0.9900
C1—C21.403 (6)C37—H37B0.9900
C1—C71.480 (6)C38—C391.499 (5)
C2—C31.381 (6)C38—H38A0.9900
C2—O81.386 (5)C38—H38B0.9900
C3—C41.391 (6)C39—C401.497 (5)
C3—C361.527 (6)C39—H39A0.9900
C4—C51.386 (6)C39—H39B0.9900
C4—H40.9500C40—C411.532 (6)
C5—C61.384 (6)C40—H40A0.9900
C5—C91.523 (6)C40—H40B0.9900
C6—O11.392 (5)C41—H41A0.9800
C7—Br11.974 (5)C41—H41B0.9800
C7—H7A0.9900C41—H41C0.9800
C7—H7B0.9900C42—C431.534 (6)
C8—O11.420 (6)C42—H42A0.9900
C8—O21.423 (5)C42—H42B0.9900
C8—H8A0.9900C43—C441.517 (6)
C8—H8B0.9900C43—H43A0.9900
C9—C121.519 (6)C43—H43B0.9900
C9—C371.535 (6)C44—C451.488 (6)
C9—H91.0000C44—H44A0.9900
C10—C111.385 (6)C44—H44B0.9900
C10—C151.400 (6)C45—C461.566 (8)
C10—C161.489 (6)C45—H45A0.9900
C11—O21.383 (5)C45—H45B0.9900
C11—C121.396 (6)C46—H46A0.9800
C12—C131.398 (6)C46—H46B0.9800
C13—C141.385 (6)C46—H46C0.9800
C13—H130.9500C47—C481.528 (6)
C14—C151.386 (6)C47—H47A0.9900
C14—C181.524 (5)C47—H47B0.9900
C15—O31.382 (5)C48—C491.506 (7)
C16—Br21.964 (4)C48—C49A1.508 (9)
C16—H16A0.9900C48—H48A0.9900
C16—H16B0.9900C48—H48B0.9900
C17—O41.412 (5)C49—C501.488 (9)
C17—O31.420 (5)C49—H49A0.9900
C17—H17A0.9900C49—H49B0.9900
C17—H17B0.9900C50—C511.484 (9)
C18—C211.512 (5)C50—H50A0.9900
C18—C421.521 (5)C50—H50B0.9900
C18—H181.0000C51—H51A0.9800
C19—C201.387 (6)C51—H51B0.9800
C19—C241.395 (6)C51—H51C0.9800
C19—C251.497 (6)C49A—C50A1.498 (10)
C20—C211.390 (6)C49A—H49C0.9900
C20—O41.394 (5)C49A—H49D0.9900
C21—C221.389 (6)C50A—C51A1.484 (10)
C22—C231.388 (5)C50A—H50C0.9900
C22—H220.9500C50A—H50D0.9900
C23—C241.384 (6)C51A—H51D0.9800
C23—C271.514 (5)C51A—H51E0.9800
C24—O51.391 (4)C51A—H51F0.9800
C25—Br31.966 (5)C52—C531.461 (7)
C25—H25A0.9900C52—C53A1.478 (8)
C25—H25B0.9900C52—H52A0.9900
C26—O51.414 (5)C52—H52B0.9900
C26—O61.424 (5)C52—H52C0.9900
C26—H26A0.9900C52—H52D0.9900
C26—H26B0.9900C53—C541.499 (5)
C27—C301.512 (5)C53—H52D0.8681
C27—C471.534 (5)C53—H53A0.9900
C27—H271.0000C53—H53B0.9900
C28—C291.397 (6)C54—C551.497 (5)
C28—C331.404 (6)C54—H54A0.9900
C28—C341.479 (5)C54—H54B0.9900
C29—O61.384 (5)C55—C561.533 (6)
C29—C301.397 (5)C55—H55A0.9900
C30—C311.388 (6)C55—H55B0.9900
C31—C321.399 (6)C56—H56A0.9800
C31—H310.9500C56—H56B0.9800
C32—C331.390 (6)C56—H56C0.9800
C32—C361.523 (6)C53A—C54A1.499 (5)
C33—O71.379 (5)C53A—H53C0.9900
C34—Br41.964 (4)C53A—H53D0.9900
C34—H34A0.9900C54A—C55A1.497 (5)
C34—H34B0.9900C54A—H54C0.9900
C35—O81.410 (5)C54A—H54D0.9900
C35—O71.438 (5)C55A—C56A1.532 (6)
C35—H35A0.9900C55A—H55C0.9900
C35—H35B0.9900C55A—H55D0.9900
C36—C521.516 (6)C56A—H56D0.9800
C36—H361.0000C56A—H56E0.9800
C37—C381.544 (6)C56A—H56F0.9800
C6—C1—C2117.3 (4)C41—C40—H40B109.0
C6—C1—C7121.6 (4)H40A—C40—H40B107.8
C2—C1—C7121.1 (4)C40—C41—H41A109.5
C3—C2—O8121.7 (4)C40—C41—H41B109.5
C3—C2—C1122.2 (4)H41A—C41—H41B109.5
O8—C2—C1116.0 (4)C40—C41—H41C109.5
C2—C3—C4117.9 (4)H41A—C41—H41C109.5
C2—C3—C36119.7 (4)H41B—C41—H41C109.5
C4—C3—C36122.3 (4)C18—C42—C43114.3 (3)
C5—C4—C3122.4 (4)C18—C42—H42A108.7
C5—C4—H4118.8C43—C42—H42A108.7
C3—C4—H4118.8C18—C42—H42B108.7
C6—C5—C4118.1 (4)C43—C42—H42B108.7
C6—C5—C9118.7 (4)H42A—C42—H42B107.6
C4—C5—C9123.2 (4)C44—C43—C42113.2 (4)
C5—C6—O1120.6 (4)C44—C43—H43A108.9
C5—C6—C1122.0 (4)C42—C43—H43A108.9
O1—C6—C1117.3 (4)C44—C43—H43B108.9
C1—C7—Br1109.9 (3)C42—C43—H43B108.9
C1—C7—H7A109.7H43A—C43—H43B107.8
Br1—C7—H7A109.7C45—C44—C43116.1 (4)
C1—C7—H7B109.7C45—C44—H44A108.3
Br1—C7—H7B109.7C43—C44—H44A108.3
H7A—C7—H7B108.2C45—C44—H44B108.3
O1—C8—O2112.0 (4)C43—C44—H44B108.3
O1—C8—H8A109.2H44A—C44—H44B107.4
O2—C8—H8A109.2C44—C45—C46113.5 (5)
O1—C8—H8B109.2C44—C45—H45A108.9
O2—C8—H8B109.2C46—C45—H45A108.9
H8A—C8—H8B107.9C44—C45—H45B108.9
C12—C9—C5108.1 (3)C46—C45—H45B108.9
C12—C9—C37113.4 (4)H45A—C45—H45B107.7
C5—C9—C37113.7 (4)C45—C46—H46A109.5
C12—C9—H9107.1C45—C46—H46B109.5
C5—C9—H9107.1H46A—C46—H46B109.5
C37—C9—H9107.1C45—C46—H46C109.5
C11—C10—C15118.1 (4)H46A—C46—H46C109.5
C11—C10—C16121.0 (4)H46B—C46—H46C109.5
C15—C10—C16120.9 (4)C48—C47—C27112.2 (3)
O2—C11—C10118.0 (4)C48—C47—H47A109.2
O2—C11—C12119.8 (4)C27—C47—H47A109.2
C10—C11—C12122.1 (4)C48—C47—H47B109.2
C11—C12—C13117.3 (4)C27—C47—H47B109.2
C11—C12—C9120.9 (4)H47A—C47—H47B107.9
C13—C12—C9121.8 (4)C49—C48—C47116.2 (8)
C14—C13—C12122.6 (4)C49A—C48—C47114.4 (18)
C14—C13—H13118.7C49—C48—H48A108.2
C12—C13—H13118.7C49A—C48—H48A97.5
C13—C14—C15117.9 (4)C47—C48—H48A108.2
C13—C14—C18121.6 (4)C49—C48—H48B108.2
C15—C14—C18120.4 (4)C49A—C48—H48B119.9
O3—C15—C14120.5 (4)C47—C48—H48B108.2
O3—C15—C10117.4 (4)H48A—C48—H48B107.4
C14—C15—C10121.9 (4)C50—C49—C48115.0 (8)
C10—C16—Br2111.0 (3)C50—C49—H49A108.5
C10—C16—H16A109.4C48—C49—H49A108.5
Br2—C16—H16A109.4C50—C49—H49B108.5
C10—C16—H16B109.4C48—C49—H49B108.5
Br2—C16—H16B109.4H49A—C49—H49B107.5
H16A—C16—H16B108.0C51—C50—C49110.5 (10)
O4—C17—O3113.0 (3)C51—C50—H50A109.6
O4—C17—H17A109.0C49—C50—H50A109.6
O3—C17—H17A109.0C51—C50—H50B109.6
O4—C17—H17B109.0C49—C50—H50B109.6
O3—C17—H17B109.0H50A—C50—H50B108.1
H17A—C17—H17B107.8C50—C51—H51A109.5
C21—C18—C42112.9 (3)C50—C51—H51B109.5
C21—C18—C14107.8 (3)H51A—C51—H51B109.5
C42—C18—C14114.4 (3)C50—C51—H51C109.5
C21—C18—H18107.1H51A—C51—H51C109.5
C42—C18—H18107.1H51B—C51—H51C109.5
C14—C18—H18107.1C50A—C49A—C48109.9 (14)
C20—C19—C24117.4 (4)C50A—C49A—H49C109.7
C20—C19—C25121.4 (4)C48—C49A—H49C109.7
C24—C19—C25121.2 (4)C50A—C49A—H49D109.7
C19—C20—C21122.9 (4)C48—C49A—H49D109.7
C19—C20—O4117.3 (4)H49C—C49A—H49D108.2
C21—C20—O4119.7 (4)C51A—C50A—C49A122.1 (18)
C22—C21—C20116.8 (4)C51A—C50A—H50C106.8
C22—C21—C18123.5 (4)C49A—C50A—H50C106.8
C20—C21—C18119.7 (3)C51A—C50A—H50D106.8
C23—C22—C21123.1 (4)C49A—C50A—H50D106.8
C23—C22—H22118.5H50C—C50A—H50D106.7
C21—C22—H22118.5C50A—C51A—H51D109.5
C24—C23—C22117.5 (4)C50A—C51A—H51E109.5
C24—C23—C27119.5 (3)H51D—C51A—H51E109.5
C22—C23—C27123.0 (4)C50A—C51A—H51F109.5
C23—C24—O5120.7 (4)H51D—C51A—H51F109.5
C23—C24—C19122.3 (4)H51E—C51A—H51F109.5
O5—C24—C19116.9 (3)C53—C52—C53A78.0 (9)
C19—C25—Br3110.5 (3)C53—C52—C36116.0 (5)
C19—C25—H25A109.6C53A—C52—C36110.2 (7)
Br3—C25—H25A109.6C53—C52—H52A108.3
C19—C25—H25B109.6C36—C52—H52A108.3
Br3—C25—H25B109.6C53—C52—H52B108.3
H25A—C25—H25B108.1C53A—C52—H52B132.7
O5—C26—O6112.9 (3)C36—C52—H52B108.3
O5—C26—H26A109.0H52A—C52—H52B107.4
O6—C26—H26A109.0C53—C52—H52C128.9
O5—C26—H26B109.0C53A—C52—H52C111.8
O6—C26—H26B109.0C36—C52—H52C107.2
H26A—C26—H26B107.8H52A—C52—H52C81.1
C30—C27—C23109.2 (3)C53A—C52—H52D112.7
C30—C27—C47114.4 (3)C36—C52—H52D107.8
C23—C27—C47113.5 (3)H52A—C52—H52D138.5
C30—C27—H27106.3H52B—C52—H52D79.7
C23—C27—H27106.3H52C—C52—H52D107.0
C47—C27—H27106.3C52—C53—C54117.6 (8)
C29—C28—C33117.5 (4)C54—C53—H52D103.1
C29—C28—C34121.5 (4)C52—C53—H53A107.9
C33—C28—C34121.0 (4)C54—C53—H53A107.9
O6—C29—C30120.8 (3)H52D—C53—H53A145.1
O6—C29—C28116.8 (3)C52—C53—H53B107.9
C30—C29—C28122.4 (4)C54—C53—H53B107.9
C31—C30—C29117.6 (4)H52D—C53—H53B77.4
C31—C30—C27123.3 (3)H53A—C53—H53B107.2
C29—C30—C27119.1 (4)C55—C54—C53114.3 (4)
C30—C31—C32122.6 (4)C55—C54—H54A108.7
C30—C31—H31118.7C53—C54—H54A108.7
C32—C31—H31118.7C55—C54—H54B108.7
C33—C32—C31117.7 (4)C53—C54—H54B108.7
C33—C32—C36119.8 (4)H54A—C54—H54B107.6
C31—C32—C36122.5 (4)C54—C55—C56113.0 (5)
O7—C33—C32120.7 (4)C54—C55—H55A109.0
O7—C33—C28117.1 (3)C56—C55—H55A109.0
C32—C33—C28122.2 (4)C54—C55—H55B109.0
C28—C34—Br4109.6 (3)C56—C55—H55B109.0
C28—C34—H34A109.8H55A—C55—H55B107.8
Br4—C34—H34A109.8C55—C56—H56A109.5
C28—C34—H34B109.8C55—C56—H56B109.5
Br4—C34—H34B109.8H56A—C56—H56B109.5
H34A—C34—H34B108.2C55—C56—H56C109.5
O8—C35—O7111.7 (3)H56A—C56—H56C109.5
O8—C35—H35A109.3H56B—C56—H56C109.5
O7—C35—H35A109.3C52—C53A—C54A115.9 (12)
O8—C35—H35B109.3C52—C53A—H53C108.3
O7—C35—H35B109.3C54A—C53A—H53C108.3
H35A—C35—H35B107.9C52—C53A—H53D108.3
C52—C36—C32114.1 (4)C54A—C53A—H53D108.3
C52—C36—C3114.3 (4)H53C—C53A—H53D107.4
C32—C36—C3108.1 (3)C55A—C54A—C53A114.3 (4)
C52—C36—H36106.6C55A—C54A—H54C108.7
C32—C36—H36106.6C53A—C54A—H54C108.7
C3—C36—H36106.6C55A—C54A—H54D108.7
C9—C37—C38112.8 (4)C53A—C54A—H54D108.7
C9—C37—H37A109.0H54C—C54A—H54D107.6
C38—C37—H37A109.0C54A—C55A—C56A113.0 (5)
C9—C37—H37B109.0C54A—C55A—H55C109.0
C38—C37—H37B109.0C56A—C55A—H55C109.0
H37A—C37—H37B107.8C54A—C55A—H55D109.0
C39—C38—C37112.8 (4)C56A—C55A—H55D109.0
C39—C38—H38A109.0H55C—C55A—H55D107.8
C37—C38—H38A109.0C55A—C56A—H56D109.5
C39—C38—H38B109.0C55A—C56A—H56E109.5
C37—C38—H38B109.0H56D—C56A—H56E109.5
H38A—C38—H38B107.8C55A—C56A—H56F109.5
C40—C39—C38114.3 (4)H56D—C56A—H56F109.5
C40—C39—H39A108.7H56E—C56A—H56F109.5
C38—C39—H39A108.7C6—O1—C8117.5 (3)
C40—C39—H39B108.7C11—O2—C8116.6 (3)
C38—C39—H39B108.7C15—O3—C17116.9 (3)
H39A—C39—H39B107.6C20—O4—C17115.8 (3)
C39—C40—C41113.0 (5)C24—O5—C26116.8 (3)
C39—C40—H40A109.0C29—O6—C26115.8 (3)
C41—C40—H40A109.0C33—O7—C35115.4 (3)
C39—C40—H40B109.0C2—O8—C35118.2 (3)
C6—C1—C2—C30.6 (6)C33—C28—C29—C302.0 (6)
C7—C1—C2—C3179.5 (4)C34—C28—C29—C30178.6 (4)
C6—C1—C2—O8176.2 (3)O6—C29—C30—C31179.6 (3)
C7—C1—C2—O83.8 (6)C28—C29—C30—C311.4 (6)
O8—C2—C3—C4177.7 (3)O6—C29—C30—C273.8 (5)
C1—C2—C3—C41.2 (6)C28—C29—C30—C27178.0 (3)
O8—C2—C3—C365.6 (6)C23—C27—C30—C3189.7 (4)
C1—C2—C3—C36177.9 (4)C47—C27—C30—C3138.8 (5)
C2—C3—C4—C51.9 (6)C23—C27—C30—C2986.7 (4)
C36—C3—C4—C5178.5 (4)C47—C27—C30—C29144.8 (4)
C3—C4—C5—C60.7 (6)C29—C30—C31—C320.2 (6)
C3—C4—C5—C9176.8 (4)C27—C30—C31—C32176.7 (4)
C4—C5—C6—O1176.7 (4)C30—C31—C32—C330.4 (6)
C9—C5—C6—O17.1 (6)C30—C31—C32—C36176.6 (4)
C4—C5—C6—C11.2 (6)C31—C32—C33—O7179.1 (3)
C9—C5—C6—C1175.1 (4)C36—C32—C33—O73.9 (6)
C2—C1—C6—C51.8 (6)C31—C32—C33—C280.2 (6)
C7—C1—C6—C5178.2 (4)C36—C32—C33—C28177.2 (4)
C2—C1—C6—O1176.1 (3)C29—C28—C33—O7179.8 (3)
C7—C1—C6—O13.8 (6)C34—C28—C33—O70.3 (5)
C6—C1—C7—Br192.4 (4)C29—C28—C33—C321.3 (6)
C2—C1—C7—Br187.6 (4)C34—C28—C33—C32179.2 (4)
C6—C5—C9—C1283.5 (4)C29—C28—C34—Br486.8 (4)
C4—C5—C9—C1292.5 (5)C33—C28—C34—Br492.7 (4)
C6—C5—C9—C37149.7 (4)C33—C32—C36—C52145.4 (4)
C4—C5—C9—C3734.3 (5)C31—C32—C36—C5237.7 (5)
C15—C10—C11—O2177.3 (3)C33—C32—C36—C386.2 (4)
C16—C10—C11—O23.5 (6)C31—C32—C36—C390.7 (5)
C15—C10—C11—C120.2 (6)C2—C3—C36—C52148.6 (4)
C16—C10—C11—C12179.3 (4)C4—C3—C36—C5234.9 (6)
O2—C11—C12—C13177.6 (3)C2—C3—C36—C3283.2 (5)
C10—C11—C12—C130.5 (6)C4—C3—C36—C3293.3 (4)
O2—C11—C12—C95.2 (5)C12—C9—C37—C3861.2 (5)
C10—C11—C12—C9177.7 (4)C5—C9—C37—C38174.7 (4)
C5—C9—C12—C1186.0 (4)C9—C37—C38—C39173.7 (4)
C37—C9—C12—C11146.9 (4)C37—C38—C39—C40174.0 (5)
C5—C9—C12—C1391.1 (4)C38—C39—C40—C41179.5 (5)
C37—C9—C12—C1336.0 (5)C21—C18—C42—C43172.5 (4)
C11—C12—C13—C141.4 (6)C14—C18—C42—C4363.7 (5)
C9—C12—C13—C14178.6 (3)C18—C42—C43—C44175.5 (4)
C12—C13—C14—C152.0 (5)C42—C43—C44—C45179.8 (5)
C12—C13—C14—C18178.8 (3)C43—C44—C45—C46179.3 (5)
C13—C14—C15—O3177.8 (3)C30—C27—C47—C4865.3 (5)
C18—C14—C15—O35.4 (5)C23—C27—C47—C48168.4 (4)
C13—C14—C15—C101.7 (5)C27—C47—C48—C49168.8 (6)
C18—C14—C15—C10178.5 (3)C27—C47—C48—C49A176.7 (11)
C11—C10—C15—O3177.0 (3)C49A—C48—C49—C5019 (9)
C16—C10—C15—O33.8 (5)C47—C48—C49—C5066.4 (14)
C11—C10—C15—C140.8 (6)C48—C49—C50—C5160.5 (15)
C16—C10—C15—C14180.0 (4)C49—C48—C49A—C50A17 (8)
C11—C10—C16—Br287.0 (4)C47—C48—C49A—C50A83 (3)
C15—C10—C16—Br292.2 (4)C48—C49A—C50A—C51A173 (2)
C13—C14—C18—C2191.7 (4)C32—C36—C52—C53165.1 (5)
C15—C14—C18—C2185.0 (4)C3—C36—C52—C5369.8 (6)
C13—C14—C18—C4234.8 (5)C32—C36—C52—C53A78.9 (10)
C15—C14—C18—C42148.5 (4)C3—C36—C52—C53A156.0 (10)
C24—C19—C20—C212.2 (6)C53A—C52—C53—C5491.1 (9)
C25—C19—C20—C21178.1 (4)C36—C52—C53—C54162.2 (6)
C24—C19—C20—O4179.3 (3)C52—C53—C54—C5567.0 (15)
C25—C19—C20—O41.0 (6)C53—C54—C55—C56171.6 (12)
C19—C20—C21—C220.4 (6)C53—C52—C53A—C54A55.5 (16)
O4—C20—C21—C22177.5 (3)C36—C52—C53A—C54A169.1 (14)
C19—C20—C21—C18177.8 (4)C52—C53A—C54A—C55A42 (2)
O4—C20—C21—C185.1 (5)C53A—C54A—C55A—C56A93 (2)
C42—C18—C21—C2235.5 (5)C5—C6—O1—C884.5 (5)
C14—C18—C21—C2291.8 (4)C1—C6—O1—C897.6 (4)
C42—C18—C21—C20147.2 (4)O2—C8—O1—C692.3 (4)
C14—C18—C21—C2085.4 (4)C10—C11—O2—C8100.7 (4)
C20—C21—C22—C230.1 (6)C12—C11—O2—C882.1 (5)
C18—C21—C22—C23177.2 (4)O1—C8—O2—C1191.4 (4)
C21—C22—C23—C241.2 (6)C14—C15—O3—C1780.7 (5)
C21—C22—C23—C27178.9 (3)C10—C15—O3—C17103.1 (4)
C22—C23—C24—O5178.9 (3)O4—C17—O3—C1592.0 (4)
C27—C23—C24—O53.3 (5)C19—C20—O4—C1799.4 (4)
C22—C23—C24—C193.1 (6)C21—C20—O4—C1783.4 (5)
C27—C23—C24—C19179.1 (3)O3—C17—O4—C2093.9 (4)
C20—C19—C24—C233.6 (6)C23—C24—O5—C2679.7 (5)
C25—C19—C24—C23176.7 (4)C19—C24—O5—C26104.3 (4)
C20—C19—C24—O5179.6 (3)O6—C26—O5—C2494.1 (4)
C25—C19—C24—O50.8 (6)C30—C29—O6—C2680.2 (4)
C20—C19—C25—Br392.9 (4)C28—C29—O6—C26101.5 (4)
C24—C19—C25—Br386.8 (4)O5—C26—O6—C2994.3 (4)
C24—C23—C27—C3086.5 (4)C32—C33—O7—C3582.8 (4)
C22—C23—C27—C3091.1 (4)C28—C33—O7—C3598.3 (4)
C24—C23—C27—C47144.4 (4)O8—C35—O7—C3393.6 (4)
C22—C23—C27—C4737.9 (5)C3—C2—O8—C3581.4 (5)
C33—C28—C29—O6179.8 (3)C1—C2—O8—C35101.9 (4)
C34—C28—C29—O60.3 (5)O7—C35—O8—C291.9 (4)

Experimental details

Crystal data
Chemical formulaC56H68Br4O8·0.415H2O
Mr1197.75
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)11.5151 (2), 11.9323 (2), 22.7986 (5)
α, β, γ (°)93.655 (1), 92.921 (1), 118.676 (1)
V3)2730.83 (9)
Z2
Radiation typeMo Kα
µ (mm1)3.00
Crystal size (mm)0.41 × 0.30 × 0.29
Data collection
DiffractometerBruker APEXII CCD area-detector
Absorption correctionIntegration
[face-indexed absorption corrections carried out with XPREP (Bruker, 2005)]
Tmin, Tmax0.373, 0.477
No. of measured, independent and
observed [I > 2σ(I)] reflections
42983, 10730, 7721
Rint0.044
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.187, 1.12
No. of reflections10730
No. of parameters649
No. of restraints102
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.41, 1.41

Computer programs: APEX2 (Bruker, 2005), SAINT-NT (Bruker, 2005), SHELXTL (Bruker, 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Version 1.4.2; Bruno et al., 2002).

 

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