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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2008 Jan 11;64(Pt 2):o423. doi: 10.1107/S1600536808000184

[4-(Methoxy­carbon­yl)benz­yl]triphenyl­phospho­nium bromide hemihydrate

Saba Nazir a, M Khawar Rauf b, Masahiro Ebihara b, Shahid Hameed a,*
PMCID: PMC2960404  PMID: 21201450

Abstract

In the crystal structure of the title compound, C27H24O2P+·Br−·0.5H2O, there are inter­molecular O—H⋯Br hydrogen bonds between the H atoms of the water of crystallization and the bromide anions. The three phenyl rings of the triphenyl­phosphonium moiety are at angles of 59.73 (15), 79.15 (14) and 82.81 (17)° with the C/P/C planes.

Related literature

For related literature, see: Ahmed et al. (1996 ▶); Harcken & Martin (2001 ▶); Kojima et al. (2002 ▶); McDonald & Campbell (1959 ▶); Nassar et al. (2004 ▶); Phillips et al. (2002 ▶); Tanaka et al. (2003 ▶); Wittig & Schöllkopf (1954 ▶).graphic file with name e-64-0o423-scheme1.jpg

Experimental

Crystal data

  • C27H24O2P+·Br−·0.5H2O

  • M r = 500.35

  • Monoclinic, Inline graphic

  • a = 21.017 (8) Å

  • b = 14.045 (5) Å

  • c = 19.868 (7) Å

  • β = 126.107 (4)°

  • V = 4738 (3) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 1.83 mm−1

  • T = 123 (2) K

  • 0.40 × 0.31 × 0.22 mm

Data collection

  • Rigaku/MSC Mercury CCD diffractometer

  • Absorption correction: integration (ABSCOR; Higashi, 1999 ▶) T min = 0.404, T max = 0.520

  • 18847 measured reflections

  • 5425 independent reflections

  • 5022 reflections with I > 2σ(I)

  • R int = 0.038

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043

  • wR(F 2) = 0.079

  • S = 1.15

  • 5425 reflections

  • 290 parameters

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

  • Δρmax = 0.51 e Å−3

  • Δρmin = −0.53 e Å−3

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2001 ▶); cell refinement: CrystalClear; data reduction: TEXSAN (Molecular Structure Corporation & Rigaku, 2004 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97 and TEXSAN.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808000184/hg2361sup1.cif

e-64-0o423-sup1.cif (22.3KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808000184/hg2361Isup2.hkl

e-64-0o423-Isup2.hkl (265.8KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O3—H3O⋯Br1 1.03 (4) 2.22 (4) 3.2308 (17) 169 (3)
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Acknowledgments

MKR is grateful to the Higher Education Commission of Pakistan for financial support under the International support initiative program for a Doctoral Fellowship at Gifu University, Japan.

supplementary crystallographic information

Comment

One of the most useful methods for the synthesis of alkenes with control over the stereoselectivity is the well known Wittig reaction (Wittig & Schöllkopf, 1954). It is mainly due to the stereoselectivity of the Wittig reagent that not only its use in the synthesis (Kojima et al., 2002; Phillips et al., 2002; Harcken & Martin, 2001) has not seen a decline but new and improved methods for its synthesis are being constantly developed (Nassar et al., 2004; Tanaka et al., 2003; Kojima et al., 2002). The title compound, (I), is an intermediate in the synthesis of (E)-hydroxyalkyl 4-(4-substituted styryl)benzoate as a part of the project to synthesize ligands for polymeric liquid crystals. Here, we are going to present the crystal structure of the title compound (I). All the geometric parameters are in agreement with the the similar type of studies made by (Ahmed et al., 1996) There are standard electrostatic interactions between the triphenyl-(4-methylcarboxy)benzylphosphonium cations and the bromide anions. It is confirmed that the compound (I) is an ion pair (Fig. 1), with a distance of 4.382 (2)Å between the P+ and Br- centres.

Experimental

The triphenyl-(4-methylcarboxy)benzylphosphonium bromide (I) was synthesized following a method reported in the literature (Mcdonald & Campbell, 1959).A mixture of methyl 4-(bromomethyl)benzoate 2.5 g, 0.01 mol) and triphenylphosphine (2.43 g, 0.01 mol) in 40 ml of toluene was heated under reflux for 3 hr. After cooling to room temperature the salt was filtered, washed with ether and dried under reduced pressure.Yield: 81%, m.p: 245–248°C, Rf = 0.11 (n-Hexane: ethylacetate 7:3). IR (KBr, νmax, cm-1): 3010, 2926, 2830, 1719, 1605, 786. 1H-NMR (CDCl3): δ 3.87 (3H, s), 5.65 (2H, d, J = 15 Hz), 7.70 (17H, m), 8.04 (2H, d, J = 8.1 Hz). 13C-NMR (75 MHz, CDCl3):δ 52.23, 30.58 (d, J = 186 Hz), 117.56 (d, J = 342 Hz),129.70 (d, J = 12 Hz), 129.87 (d, J = 18 Hz), 130.165 (d, J = 51 Hz), 131.73 (d, J = 21 Hz), 132.80 (d, J = 33 Hz), 134.45 (d, J = 36 Hz), 166.54.

Refinement

H atom on the N atom was refined isotropically. Other H atoms were placed in idealized positions and treated as riding atoms with C—H distance in the range 0.95–0.99 Å and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C).

Figures

Fig. 1.

Fig. 1.

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Molecular structure of (I) showing atom-labelling scheme and displacement ellipsoids at the 30% probability level.

Crystal data

C27H24O2P+·Br–·0.5H2O F000 = 2056
Mr = 500.35 Dx = 1.403 Mg m−3
Monoclinic, C2/c Mo Kα radiation λ = 0.71070 Å
Hall symbol: -C 2yc Cell parameters from 7012 reflections
a = 21.017 (8) Å θ = 3.1–27.5º
b = 14.045 (5) Å µ = 1.83 mm−1
c = 19.868 (7) Å T = 123 (2) K
β = 126.107 (4)º Block, colorless
V = 4738 (3) Å3 0.40 × 0.31 × 0.22 mm
Z = 8
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Data collection

Rigaku/MSC Mercury CCD diffractometer 5022 reflections with I > 2σ(I)
Monochromator: graphite Rint = 0.038
T = 123(2) K θmax = 27.5º
ω scans θmin = 3.2º
Absorption correction: integration(ABSCOR; Higashi, 1999) h = −27→25
Tmin = 0.404, Tmax = 0.520 k = −18→17
18847 measured reflections l = −18→25
5425 independent reflections
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Refinement

Refinement on F2 Secondary atom site location: difference Fourier map
Least-squares matrix: full Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043 H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.079   w = 1/[σ2(Fo2) + (0.0133P)2 + 10.1118P] where P = (Fo2 + 2Fc2)/3
S = 1.15 (Δ/σ)max = 0.001
5425 reflections Δρmax = 0.51 e Å−3
290 parameters Δρmin = −0.53 e Å−3
Primary atom site location: structure-invariant direct methods Extinction correction: none
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Special details

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

x y z Uiso*/Ueq
P1 0.31029 (3) 0.44471 (4) 0.32117 (3) 0.01545 (12)
C1 0.41411 (12) 0.41713 (15) 0.38823 (13) 0.0174 (4)
H1A 0.4424 0.4655 0.3789 0.021*
H1B 0.4324 0.4234 0.4468 0.021*
C2 0.43759 (12) 0.32001 (16) 0.37752 (12) 0.0181 (4)
C3 0.42000 (13) 0.23839 (16) 0.40364 (13) 0.0206 (5)
H3 0.3909 0.2438 0.4261 0.025*
C4 0.44456 (13) 0.14960 (17) 0.39714 (14) 0.0222 (5)
H4 0.4314 0.0945 0.4143 0.027*
C5 0.48845 (12) 0.14061 (16) 0.36557 (13) 0.0205 (5)
C6 0.50870 (13) 0.22217 (18) 0.34252 (14) 0.0249 (5)
H6 0.5408 0.2170 0.3235 0.030*
C7 0.48255 (13) 0.31103 (18) 0.34700 (14) 0.0241 (5)
H7 0.4953 0.3660 0.3292 0.029*
C8 0.51658 (13) 0.04628 (18) 0.35787 (14) 0.0260 (5)
O1 0.56546 (10) 0.03619 (14) 0.34485 (11) 0.0341 (4)
O2 0.48183 (10) −0.02626 (12) 0.36867 (12) 0.0343 (4)
C9 0.50683 (18) −0.1213 (2) 0.3647 (2) 0.0495 (8)
H9A 0.4922 −0.1329 0.3085 0.074*
H9B 0.4811 −0.1685 0.3776 0.074*
H9C 0.5641 −0.1266 0.4052 0.074*
C10 0.27533 (12) 0.45605 (15) 0.21423 (13) 0.0167 (4)
C11 0.19410 (13) 0.45949 (17) 0.15136 (13) 0.0217 (5)
H11 0.1578 0.4523 0.1648 0.026*
C12 0.16704 (14) 0.47353 (17) 0.06923 (14) 0.0252 (5)
H12 0.1120 0.4762 0.0265 0.030*
C13 0.21980 (14) 0.48367 (16) 0.04915 (14) 0.0240 (5)
H13 0.2008 0.4929 −0.0072 0.029*
C14 0.30000 (14) 0.48039 (17) 0.11111 (14) 0.0243 (5)
H14 0.3361 0.4875 0.0974 0.029*
C15 0.32787 (13) 0.46655 (16) 0.19402 (13) 0.0212 (5)
H15 0.3830 0.4643 0.2366 0.025*
C16 0.29724 (13) 0.55555 (15) 0.35705 (13) 0.0182 (4)
C17 0.22172 (14) 0.58176 (18) 0.33081 (17) 0.0311 (6)
H17 0.1780 0.5419 0.2939 0.037*
C18 0.21096 (16) 0.66619 (19) 0.35887 (18) 0.0363 (6)
H18 0.1596 0.6842 0.3409 0.044*
C19 0.27431 (15) 0.72433 (17) 0.41278 (15) 0.0280 (5)
H19 0.2665 0.7816 0.4325 0.034*
C20 0.34886 (14) 0.69949 (17) 0.43800 (14) 0.0253 (5)
H20 0.3921 0.7402 0.4744 0.030*
C21 0.36103 (13) 0.61531 (17) 0.41050 (13) 0.0221 (5)
H21 0.4124 0.5984 0.4279 0.027*
C22 0.25177 (12) 0.35735 (15) 0.32766 (13) 0.0171 (4)
C23 0.24544 (13) 0.36231 (17) 0.39383 (14) 0.0223 (5)
H23 0.2734 0.4097 0.4356 0.027*
C24 0.19816 (14) 0.29762 (18) 0.39790 (15) 0.0265 (5)
H24 0.1933 0.3011 0.4424 0.032*
C25 0.15793 (14) 0.22790 (18) 0.33766 (16) 0.0281 (5)
H25 0.1248 0.1846 0.3404 0.034*
C26 0.16576 (15) 0.22106 (18) 0.27322 (16) 0.0287 (5)
H26 0.1388 0.1725 0.2324 0.034*
C27 0.21322 (13) 0.28556 (16) 0.26844 (14) 0.0230 (5)
H27 0.2193 0.2806 0.2248 0.028*
Br1 0.456153 (14) 0.381335 (18) 0.588418 (14) 0.02564 (7)
O3 0.5000 0.49982 (19) 0.7500 0.0300 (5)
H3O 0.485 (2) 0.455 (3) 0.702 (2) 0.090 (14)*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
P1 0.0136 (2) 0.0170 (3) 0.0155 (2) −0.0005 (2) 0.0084 (2) 0.0006 (2)
C1 0.0142 (9) 0.0186 (10) 0.0169 (10) −0.0006 (8) 0.0077 (8) 0.0010 (8)
C2 0.0129 (9) 0.0227 (11) 0.0153 (9) 0.0020 (8) 0.0064 (8) 0.0026 (8)
C3 0.0206 (11) 0.0213 (11) 0.0230 (11) −0.0003 (9) 0.0146 (9) 0.0007 (9)
C4 0.0208 (11) 0.0208 (11) 0.0260 (11) −0.0012 (9) 0.0144 (10) −0.0006 (9)
C5 0.0146 (10) 0.0261 (12) 0.0147 (10) 0.0029 (8) 0.0053 (8) −0.0020 (8)
C6 0.0200 (11) 0.0386 (14) 0.0201 (10) 0.0080 (10) 0.0140 (9) 0.0060 (10)
C7 0.0208 (11) 0.0294 (13) 0.0227 (11) 0.0054 (10) 0.0132 (9) 0.0101 (10)
C8 0.0173 (11) 0.0318 (13) 0.0184 (11) 0.0062 (10) 0.0047 (9) −0.0048 (9)
O1 0.0263 (9) 0.0428 (11) 0.0333 (9) 0.0090 (8) 0.0176 (8) −0.0058 (8)
O2 0.0256 (9) 0.0222 (9) 0.0494 (11) 0.0018 (7) 0.0189 (9) −0.0084 (8)
C9 0.0380 (16) 0.0257 (14) 0.078 (2) 0.0020 (12) 0.0304 (16) −0.0167 (15)
C10 0.0177 (10) 0.0144 (10) 0.0174 (10) 0.0010 (8) 0.0100 (9) 0.0024 (8)
C11 0.0197 (11) 0.0266 (12) 0.0195 (10) 0.0039 (9) 0.0121 (9) 0.0022 (9)
C12 0.0204 (11) 0.0298 (13) 0.0185 (10) 0.0031 (10) 0.0077 (9) 0.0019 (9)
C13 0.0305 (12) 0.0228 (12) 0.0183 (10) 0.0019 (10) 0.0143 (10) 0.0027 (9)
C14 0.0291 (12) 0.0274 (12) 0.0231 (11) −0.0023 (10) 0.0190 (10) 0.0021 (9)
C15 0.0185 (10) 0.0236 (12) 0.0204 (10) −0.0018 (9) 0.0109 (9) 0.0011 (9)
C16 0.0186 (10) 0.0171 (10) 0.0188 (10) 0.0007 (8) 0.0110 (9) 0.0012 (8)
C17 0.0184 (11) 0.0266 (13) 0.0435 (15) −0.0029 (10) 0.0156 (11) −0.0082 (11)
C18 0.0274 (13) 0.0282 (14) 0.0588 (18) 0.0024 (11) 0.0283 (13) −0.0050 (12)
C19 0.0387 (14) 0.0191 (12) 0.0342 (13) 0.0025 (10) 0.0258 (12) −0.0011 (10)
C20 0.0260 (12) 0.0220 (12) 0.0203 (11) −0.0020 (9) 0.0094 (10) −0.0039 (9)
C21 0.0181 (10) 0.0233 (11) 0.0205 (10) 0.0016 (9) 0.0088 (9) −0.0008 (9)
C22 0.0144 (10) 0.0180 (11) 0.0182 (10) −0.0003 (8) 0.0092 (8) 0.0013 (8)
C23 0.0215 (11) 0.0256 (12) 0.0212 (11) −0.0001 (9) 0.0134 (9) 0.0005 (9)
C24 0.0284 (12) 0.0319 (13) 0.0268 (12) 0.0044 (10) 0.0205 (10) 0.0072 (10)
C25 0.0282 (12) 0.0236 (12) 0.0413 (14) −0.0011 (10) 0.0255 (12) 0.0058 (10)
C26 0.0308 (13) 0.0243 (12) 0.0350 (13) −0.0084 (10) 0.0217 (11) −0.0059 (10)
C27 0.0258 (12) 0.0223 (12) 0.0238 (11) −0.0034 (9) 0.0162 (10) −0.0020 (9)
Br1 0.02436 (12) 0.03282 (14) 0.02411 (12) −0.00150 (10) 0.01670 (10) 0.00167 (10)
O3 0.0276 (13) 0.0313 (14) 0.0331 (13) 0.000 0.0190 (11) 0.000
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Geometric parameters (Å, °)

P1—C22 1.795 (2) C12—H12 0.9500
P1—C16 1.799 (2) C13—C14 1.383 (3)
P1—C10 1.800 (2) C13—H13 0.9500
P1—C1 1.806 (2) C14—C15 1.399 (3)
C1—C2 1.508 (3) C14—H14 0.9500
C1—H1A 0.9900 C15—H15 0.9500
C1—H1B 0.9900 C16—C17 1.397 (3)
C2—C3 1.395 (3) C16—C21 1.397 (3)
C2—C7 1.397 (3) C17—C18 1.384 (4)
C3—C4 1.385 (3) C17—H17 0.9500
C3—H3 0.9500 C18—C19 1.381 (4)
C4—C5 1.393 (3) C18—H18 0.9500
C4—H4 0.9500 C19—C20 1.379 (4)
C5—C6 1.390 (3) C19—H19 0.9500
C5—C8 1.495 (3) C20—C21 1.388 (3)
C6—C7 1.388 (3) C20—H20 0.9500
C6—H6 0.9500 C21—H21 0.9500
C7—H7 0.9500 C22—C27 1.391 (3)
C8—O1 1.207 (3) C22—C23 1.399 (3)
C8—O2 1.343 (3) C23—C24 1.384 (3)
O2—C9 1.454 (3) C23—H23 0.9500
C9—H9A 0.9800 C24—C25 1.383 (4)
C9—H9B 0.9800 C24—H24 0.9500
C9—H9C 0.9800 C25—C26 1.387 (4)
C10—C15 1.388 (3) C25—H25 0.9500
C10—C11 1.401 (3) C26—C27 1.392 (3)
C11—C12 1.390 (3) C26—H26 0.9500
C11—H11 0.9500 C27—H27 0.9500
C12—C13 1.389 (3) O3—H3O 1.03 (4)
C22—P1—C16 107.00 (11) C13—C12—H12 119.7
C22—P1—C10 108.96 (10) C11—C12—H12 119.7
C16—P1—C10 109.85 (10) C14—C13—C12 120.1 (2)
C22—P1—C1 112.43 (10) C14—C13—H13 120.0
C16—P1—C1 107.06 (10) C12—C13—H13 120.0
C10—P1—C1 111.41 (10) C13—C14—C15 119.8 (2)
C2—C1—P1 116.34 (15) C13—C14—H14 120.1
C2—C1—H1A 108.2 C15—C14—H14 120.1
P1—C1—H1A 108.2 C10—C15—C14 120.2 (2)
C2—C1—H1B 108.2 C10—C15—H15 119.9
P1—C1—H1B 108.2 C14—C15—H15 119.9
H1A—C1—H1B 107.4 C17—C16—C21 119.7 (2)
C3—C2—C7 118.9 (2) C17—C16—P1 119.02 (17)
C3—C2—C1 120.7 (2) C21—C16—P1 121.27 (17)
C7—C2—C1 120.3 (2) C18—C17—C16 119.7 (2)
C4—C3—C2 120.7 (2) C18—C17—H17 120.2
C4—C3—H3 119.7 C16—C17—H17 120.2
C2—C3—H3 119.7 C19—C18—C17 120.5 (2)
C3—C4—C5 120.4 (2) C19—C18—H18 119.8
C3—C4—H4 119.8 C17—C18—H18 119.8
C5—C4—H4 119.8 C20—C19—C18 120.1 (2)
C6—C5—C4 119.1 (2) C20—C19—H19 119.9
C6—C5—C8 118.7 (2) C18—C19—H19 119.9
C4—C5—C8 122.2 (2) C19—C20—C21 120.4 (2)
C7—C6—C5 120.7 (2) C19—C20—H20 119.8
C7—C6—H6 119.7 C21—C20—H20 119.8
C5—C6—H6 119.7 C20—C21—C16 119.6 (2)
C6—C7—C2 120.2 (2) C20—C21—H21 120.2
C6—C7—H7 119.9 C16—C21—H21 120.2
C2—C7—H7 119.9 C27—C22—C23 120.0 (2)
O1—C8—O2 123.9 (2) C27—C22—P1 121.14 (17)
O1—C8—C5 124.3 (2) C23—C22—P1 118.82 (16)
O2—C8—C5 111.8 (2) C24—C23—C22 119.4 (2)
C8—O2—C9 116.1 (2) C24—C23—H23 120.3
O2—C9—H9A 109.5 C22—C23—H23 120.3
O2—C9—H9B 109.5 C25—C24—C23 120.5 (2)
H9A—C9—H9B 109.5 C25—C24—H24 119.7
O2—C9—H9C 109.5 C23—C24—H24 119.7
H9A—C9—H9C 109.5 C24—C25—C26 120.2 (2)
H9B—C9—H9C 109.5 C24—C25—H25 119.9
C15—C10—C11 119.9 (2) C26—C25—H25 119.9
C15—C10—P1 120.68 (16) C25—C26—C27 119.8 (2)
C11—C10—P1 119.38 (17) C25—C26—H26 120.1
C12—C11—C10 119.5 (2) C27—C26—H26 120.1
C12—C11—H11 120.3 C22—C27—C26 119.9 (2)
C10—C11—H11 120.3 C22—C27—H27 120.1
C13—C12—C11 120.5 (2) C26—C27—H27 120.1
C22—P1—C1—C2 54.37 (19) C11—C10—C15—C14 −0.1 (3)
C16—P1—C1—C2 171.59 (16) P1—C10—C15—C14 −176.59 (18)
C10—P1—C1—C2 −68.29 (19) C13—C14—C15—C10 0.0 (4)
P1—C1—C2—C3 −71.4 (2) C22—P1—C16—C17 −43.1 (2)
P1—C1—C2—C7 113.4 (2) C10—P1—C16—C17 75.1 (2)
C7—C2—C3—C4 −1.9 (3) C1—P1—C16—C17 −163.83 (19)
C1—C2—C3—C4 −177.2 (2) C22—P1—C16—C21 136.78 (19)
C2—C3—C4—C5 1.1 (3) C10—P1—C16—C21 −105.09 (19)
C3—C4—C5—C6 1.5 (3) C1—P1—C16—C21 16.0 (2)
C3—C4—C5—C8 179.7 (2) C21—C16—C17—C18 −0.8 (4)
C4—C5—C6—C7 −3.1 (3) P1—C16—C17—C18 179.1 (2)
C8—C5—C6—C7 178.7 (2) C16—C17—C18—C19 −0.3 (4)
C5—C6—C7—C2 2.2 (3) C17—C18—C19—C20 1.2 (4)
C3—C2—C7—C6 0.3 (3) C18—C19—C20—C21 −1.0 (4)
C1—C2—C7—C6 175.6 (2) C19—C20—C21—C16 −0.1 (4)
C6—C5—C8—O1 11.6 (3) C17—C16—C21—C20 1.0 (3)
C4—C5—C8—O1 −166.6 (2) P1—C16—C21—C20 −178.90 (17)
C6—C5—C8—O2 −169.47 (19) C16—P1—C22—C27 144.04 (18)
C4—C5—C8—O2 12.3 (3) C10—P1—C22—C27 25.3 (2)
O1—C8—O2—C9 0.5 (3) C1—P1—C22—C27 −98.69 (19)
C5—C8—O2—C9 −178.4 (2) C16—P1—C22—C23 −36.1 (2)
C22—P1—C10—C15 −140.05 (18) C10—P1—C22—C23 −154.78 (17)
C16—P1—C10—C15 103.04 (19) C1—P1—C22—C23 81.2 (2)
C1—P1—C10—C15 −15.4 (2) C27—C22—C23—C24 −2.5 (3)
C22—P1—C10—C11 43.5 (2) P1—C22—C23—C24 177.58 (17)
C16—P1—C10—C11 −73.5 (2) C22—C23—C24—C25 0.6 (4)
C1—P1—C10—C11 168.08 (17) C23—C24—C25—C26 1.2 (4)
C15—C10—C11—C12 −0.1 (3) C24—C25—C26—C27 −1.1 (4)
P1—C10—C11—C12 176.46 (18) C23—C22—C27—C26 2.6 (3)
C10—C11—C12—C13 0.3 (4) P1—C22—C27—C26 −177.47 (18)
C11—C12—C13—C14 −0.4 (4) C25—C26—C27—C22 −0.8 (4)
C12—C13—C14—C15 0.2 (4)
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Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A
O3—H3O···Br1 1.03 (4) 2.22 (4) 3.2308 (17) 169 (3)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2361).

References

  1. Ahmed, S. Z., Glidewell, C. & Ferguson, G. (1996). Acta Cryst. C52, 1634–1636.
  2. Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst.32, 115–119.
  3. Harcken, C. & Martin, S. F. (2001). Org. Lett.3, 3591–3593. [DOI] [PubMed]
  4. Higashi, T. (1999). NUMABS Rigaku Corporation, Tokyo, Japan.
  5. Johnson, C. K. (1976). ORTEPII Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
  6. Kojima, S., Sugino, M., Matsukawa, S., Nakamoto, M. & Akiba, K. (2002). J. Am. Chem. Soc.124, 7674–7675. [DOI] [PubMed]
  7. McDonald, R. N. & Campbell, T. W. (1959). J. Org. Chem.24, 1969–1975.
  8. Molecular Structure Corporation & Rigaku (2001). Crystal Clear Version 1.3. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
  9. Molecular Structure Corporation & Rigaku (2004). TEXSAN Version 2.0. MSC, The Woodlands, Texas USA, and Rigaku Corporation, Tokyo, Japan.
  10. Nassar, R., Noll, B. C. & Henderson, K. W. (2004). Polyhedron, 23, 2499–2506.
  11. Phillips, G., Fevig, T. L., Lau, P. H., Klemm, G. H., Mao, M. K., Ma, C., Gloeckner, J. A. & Clark, A. S. (2002). Org. Process. Res. Dev.6, 357–366.
  12. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  13. Tanaka, K., Hata, T., Hara, H. & Katsumura, S. (2003). Tetrahedron, 59, 4945–4952.
  14. Wittig, G. & Schöllkopf, U. (1954). Chem. Ber.87, 1318–1330.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808000184/hg2361sup1.cif

e-64-0o423-sup1.cif (22.3KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808000184/hg2361Isup2.hkl

e-64-0o423-Isup2.hkl (265.8KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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