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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3149
https://doi.org/10.1107/S1600536811044849

Iso­propyl­tri­phenyl­phospho­nium bromide monohydrate

Hai Wang,a Xi-Man Zhang,a Ping Lia and Hong-Yu Chena*

aSchool of Chemistry and Chemical Engineering, TaiShan Medical University, Tai'an 271016, People's Republic of China
*Correspondence e-mail: binboll@126.com

(Received 4 October 2011; accepted 26 October 2011; online 2 November 2011)

In the title water-solvated salt, C21H22P+·Br−·H2O, the ionic components are linked by short C—H⋯Br contacts along the a-axis direction. The two half occupied water mol­ecules are connected to each other by strong O—H⋯O hydrogen bonds and they are also linked to the bromide anion by short O—H⋯Br contacts.

Related literature

For information on phase-transfer catalysts, see: Asai et al. (1994[Asai, S., Nakamura, H., Tanabe, M. & Sakamoto, K. (1994). Ind. Eng. Chem. Res. 33, 1687-1691]). For the crystal structure of tetra­phenyl­phospho­niuum bromide, see: Alcock et al. (1985[Alcock, N. W., Pennington, M. & Willey, G. R. (1985). Acta Cryst. C41, 1549-1550.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data

  • C21H22P+·Br−·H2O

  • Mr = 403.28

  • Orthorhombic, P 21 21 21

  • a = 9.078 (5) Å

  • b = 13.043 (5) Å

  • c = 17.755 (5) Å

  • V = 2102.3 (15) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 2.04 mm−1

  • T = 293 K

  • 0.20 × 0.15 × 0.13 mm
Data collection

  • Brucker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.668, Tmax = 0.688

  • 12177 measured reflections

  • 4250 independent reflections

  • 3331 reflections with I > 2σ(I)

  • Rint = 0.034
Refinement

  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.140

  • S = 1.03

  • 4250 reflections

  • 228 parameters

  • 6 restraints

  • H-atom parameters constrained

  • Δρmax = 0.82 e Å−3

  • Δρmin = −0.28 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1799 Friedel pairs

  • Flack parameter: 0.014 (13)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1O1⋯Br1i 0.85 2.86 3.701 (8) 169
O1—H2O1⋯O2 0.85 2.20 2.960 (11) 149
O2—H1O2⋯Br1ii 0.85 2.68 3.526 (7) 175
O2—H2O2⋯Br1iii 0.85 2.81 3.598 (8) 154
C19—H19⋯Br1iv 0.98 2.76 3.723 (4) 169
Symmetry codes: (i) [-x+{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}]; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [-x+{\script{3\over 2}}, -y+1, z+{\script{1\over 2}}]; (iv) x, y, z+1.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811044849/su2327sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811044849/su2327Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811044849/su2327Isup3.cml

checkCIF report


Comment top

The title compound belongs to a family of phase transfer catalysts, which usually contain large alkyl or aryl ions, such as R4N+,R4P+,R4B- etc. Because of their ease of dissolution in water, such salts have a conveninient to satisfactory hydrophobic hydration(Asai, et al., 1994).

The asymmetry unit of the title structure consists of one isopropyltriphenylphosphonium cation, one bromide anion and two half occupied water molecules (Fig. 1). In contrast with tetraphenylphosphonium salts, the major character of the cation of the title compound is that one phenyl group has been substituted by an isopropyl group. The fluctuation of the Cphenyl—P1 bond lengths in the title compound [from 1.789 (4)–1.806 (4) Å] is similar to that in the crystal structure of tetraphenylphosphonium bromide [1.801 (3)Å; Alcock, et al., 1985]. The bonds between P1 and the C atoms of phenyl rings are Csp2—Psp3 bonds, but the connection between P1 and isopropyl group is typically an Csp3—Psp3 bond (Allen, et al., 1987). The bond length of C19—P1 [1.818 (3) Å] associated with the isopropyl group is longer than that involving the phenyl groups, which vary from 1.789 (4) - 1.806 (4) Å.

In the crystal the water molecules are linked to the Br anion by short O—H···Br contacts, and the two half occupied water molecules are connected to one another by strong O-H···O hydrogen bonds (Table 1 and Fig. 2). The large cations and bromide anions are linked by short C19—H19···Br1 contacts (Table 1 and Fig. 2). These weak interactions also that play an important role in the stabilization of the crystal structure.

Related literature top

For information on phase-transfer catalysts, see: Asai et al. (1994). For the crystal structure of tetraphenylphosphoniuum bromide, see: Alcock et al. (1985). For standard bond lengths, see: Allen et al. (1987).

Experimental top

Triphenyl phosphine (10.5 g) and 2-bromopropane (4.2 mL) were placed in a teflon lined tube. The sealed tube was placed in an autoclave and heated to 433 K for 48 h, then cooled at a rate of 10 K/min. Colourless block-like crystals of the title compound were obtained.

Refinement top

The water H atoms were located in difference Fourier maps and were subsequently treated as riding atoms: O—H = 0.85 Å with Uiso(H) = 1.5Ueq(O). The C-bound H-atoms were included in calculated positions and treated as riding atoms: C-H = 0.93, 0.96, and 0.98 Å for CH(aromatic), CH3, and CH(methine) H-atoms, respectively, with = k × Ueq(parent C-atom), where k = 1.5 for CH3 H-atoms and k = 1.2 for all other H-atoms.

Structure description top

The title compound belongs to a family of phase transfer catalysts, which usually contain large alkyl or aryl ions, such as R4N+,R4P+,R4B- etc. Because of their ease of dissolution in water, such salts have a conveninient to satisfactory hydrophobic hydration(Asai, et al., 1994).

The asymmetry unit of the title structure consists of one isopropyltriphenylphosphonium cation, one bromide anion and two half occupied water molecules (Fig. 1). In contrast with tetraphenylphosphonium salts, the major character of the cation of the title compound is that one phenyl group has been substituted by an isopropyl group. The fluctuation of the Cphenyl—P1 bond lengths in the title compound [from 1.789 (4)–1.806 (4) Å] is similar to that in the crystal structure of tetraphenylphosphonium bromide [1.801 (3)Å; Alcock, et al., 1985]. The bonds between P1 and the C atoms of phenyl rings are Csp2—Psp3 bonds, but the connection between P1 and isopropyl group is typically an Csp3—Psp3 bond (Allen, et al., 1987). The bond length of C19—P1 [1.818 (3) Å] associated with the isopropyl group is longer than that involving the phenyl groups, which vary from 1.789 (4) - 1.806 (4) Å.

In the crystal the water molecules are linked to the Br anion by short O—H···Br contacts, and the two half occupied water molecules are connected to one another by strong O-H···O hydrogen bonds (Table 1 and Fig. 2). The large cations and bromide anions are linked by short C19—H19···Br1 contacts (Table 1 and Fig. 2). These weak interactions also that play an important role in the stabilization of the crystal structure.

For information on phase-transfer catalysts, see: Asai et al. (1994). For the crystal structure of tetraphenylphosphoniuum bromide, see: Alcock et al. (1985). For standard bond lengths, see: Allen et al. (1987).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of the title compound, with the numbering scheme and thermal ellipsoids drawn at the 30%probability level.
[Figure 2] Fig. 2. A view of the crystal packing of the title compound, showing the O-H···Br and O-H···O hydrogen bonds, and the C-H···Br contacts as dashed lines [H atoms not involved in these contacts have been omitted for calrity].
Isopropyltriphenylphosphonium bromide monohydrate top
Crystal data top
C21H22P+·Br−·H2OF(000) = 832
Mr = 403.28Dx = 1.274 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2ac 2abCell parameters from 3565 reflections
a = 9.078 (5) Åθ = 2.5–23.5°
b = 13.043 (5) ŵ = 2.04 mm−1
c = 17.755 (5) ÅT = 293 K
V = 2102.3 (15) Å3ROD, colourless
Z = 40.20 × 0.15 × 0.13 mm
Data collection top
Brucker APEXII CCD area-detector
diffractometer		4250 independent reflections
Radiation source: fine-focus sealed tube3331 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
phi and ω scansθmax = 26.4°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −7→11
Tmin = 0.668, Tmax = 0.688k = −16→15
12177 measured reflectionsl = −21→21
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)] = 0.049H-atom parameters constrained
wR(F2) = 0.140 w = 1/[σ2(Fo2) + (0.0853P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
4250 reflectionsΔρmax = 0.82 e Å−3
228 parametersΔρmin = −0.28 e Å−3
6 restraintsAbsolute structure: Flack (1983), 1799 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.014 (13)
Crystal data top
C21H22P+·Br−·H2OV = 2102.3 (15) Å3
Mr = 403.28Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 9.078 (5) ŵ = 2.04 mm−1
b = 13.043 (5) ÅT = 293 K
c = 17.755 (5) Å0.20 × 0.15 × 0.13 mm
Data collection top
Brucker APEXII CCD area-detector
diffractometer		4250 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3331 reflections with I > 2σ(I)
Tmin = 0.668, Tmax = 0.688Rint = 0.034
12177 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.140Δρmax = 0.82 e Å−3
S = 1.03Δρmin = −0.28 e Å−3
4250 reflectionsAbsolute structure: Flack (1983), 1799 Friedel pairs
228 parametersAbsolute structure parameter: 0.014 (13)
6 restraints
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)
Br10.46181 (8)0.58731 (5)0.00805 (3)0.0720 (2)
C10.2804 (4)0.5002 (3)0.7564 (2)0.0320 (8)
C20.2503 (5)0.4645 (3)0.8289 (3)0.0468 (11)
H20.27220.50500.87050.056*
C30.1873 (6)0.3679 (4)0.8386 (3)0.0570 (13)
H30.16900.34330.88680.068*
C40.1527 (5)0.3098 (3)0.7778 (3)0.0502 (13)
H40.10750.24660.78500.060*
C50.1833 (5)0.3426 (3)0.7054 (3)0.0463 (12)
H50.16070.30110.66440.056*
C60.2478 (4)0.4378 (3)0.6943 (2)0.0371 (9)
H60.26940.46020.64580.045*
C70.3207 (5)0.6876 (3)0.6626 (2)0.0340 (9)
C80.4105 (6)0.7668 (3)0.6355 (3)0.0493 (12)
H80.50320.77700.65640.059*
C90.3631 (8)0.8296 (4)0.5783 (3)0.0737 (18)
H90.42280.88220.56040.088*
C100.2238 (10)0.8130 (5)0.5476 (3)0.082 (2)
H100.18930.85610.50980.098*
C110.1386 (7)0.7354 (6)0.5719 (3)0.0754 (18)
H110.04780.72390.54910.090*
C120.1835 (5)0.6726 (4)0.6299 (3)0.0498 (12)
H120.12230.62050.64710.060*
C130.5706 (4)0.5878 (3)0.7380 (2)0.0312 (8)
C140.6312 (5)0.5673 (3)0.6682 (3)0.0430 (10)
H140.57650.57660.62450.052*
C150.7767 (5)0.5321 (3)0.6648 (3)0.0538 (14)
H150.81990.51870.61830.065*
C160.8552 (5)0.5173 (3)0.7293 (4)0.0567 (14)
H160.95140.49300.72640.068*
C170.7943 (5)0.5379 (4)0.7989 (3)0.0569 (14)
H170.84930.52770.84250.068*
C180.6508 (4)0.5737 (3)0.8037 (3)0.0446 (11)
H180.60890.58800.85030.054*
C190.3403 (5)0.7009 (3)0.8260 (2)0.0352 (9)
H190.36550.66180.87130.042*
C200.4348 (6)0.7974 (3)0.8257 (3)0.0538 (13)
H20A0.40540.84080.78470.081*
H20B0.53650.77890.81980.081*
H20C0.42200.83340.87240.081*
C210.1779 (5)0.7266 (4)0.8303 (3)0.0530 (12)
H21A0.15930.76690.87450.079*
H21B0.12160.66440.83270.079*
H21C0.14980.76480.78640.079*
O10.4288 (9)0.4940 (6)0.5103 (4)0.0650 (19)0.50
H1O10.34050.47450.50270.097*0.50
H2O10.47220.44690.48550.097*0.50
O20.6608 (8)0.3426 (5)0.4736 (4)0.0566 (18)0.50
H1O20.63700.27970.47770.085*0.50
H2O20.75220.33650.48350.085*0.50
P10.37744 (10)0.61951 (7)0.74506 (6)0.0269 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0904 (5)0.0823 (4)0.0433 (3)0.0170 (3)−0.0098 (3)0.0009 (3)
C10.0245 (18)0.0290 (17)0.042 (2)0.0013 (15)0.0014 (18)0.0014 (17)
C20.054 (3)0.039 (2)0.047 (3)−0.008 (2)0.000 (2)0.005 (2)
C30.062 (3)0.048 (3)0.061 (3)−0.016 (3)0.000 (3)0.019 (2)
C40.035 (3)0.032 (2)0.084 (4)−0.0057 (18)−0.004 (2)0.004 (2)
C50.035 (2)0.035 (2)0.068 (3)−0.001 (2)−0.006 (2)−0.018 (2)
C60.033 (2)0.037 (2)0.041 (2)0.0025 (18)0.0034 (18)−0.0061 (18)
C70.033 (2)0.032 (2)0.036 (2)0.0060 (17)0.0020 (18)0.0009 (17)
C80.059 (3)0.040 (2)0.049 (3)0.000 (2)0.006 (2)0.006 (2)
C90.111 (5)0.050 (3)0.061 (4)0.020 (3)0.026 (4)0.021 (3)
C100.125 (6)0.077 (4)0.042 (3)0.043 (4)−0.001 (4)0.021 (3)
C110.071 (4)0.110 (5)0.045 (3)0.026 (4)−0.017 (3)0.006 (3)
C120.043 (3)0.064 (3)0.043 (3)0.014 (2)−0.006 (2)0.005 (2)
C130.0247 (17)0.0274 (17)0.042 (2)0.0007 (14)0.0065 (16)−0.0011 (17)
C140.041 (2)0.036 (2)0.053 (3)0.000 (2)0.009 (2)−0.0011 (19)
C150.041 (3)0.042 (3)0.079 (4)0.000 (2)0.028 (3)−0.007 (3)
C160.029 (2)0.038 (2)0.104 (5)0.0034 (19)0.016 (3)0.006 (3)
C170.035 (3)0.053 (3)0.083 (4)0.003 (2)−0.007 (3)0.016 (3)
C180.030 (2)0.049 (3)0.055 (3)0.006 (2)0.0002 (19)0.004 (2)
C190.037 (2)0.032 (2)0.036 (2)0.0005 (17)0.0023 (18)−0.0023 (16)
C200.053 (3)0.037 (2)0.071 (3)−0.009 (2)0.008 (3)−0.010 (2)
C210.036 (2)0.061 (3)0.061 (3)0.009 (2)0.006 (2)−0.012 (2)
O10.072 (5)0.077 (5)0.045 (4)−0.015 (4)−0.011 (4)0.001 (3)
O20.062 (4)0.059 (4)0.049 (4)−0.009 (3)0.008 (3)0.013 (3)
P10.0222 (4)0.0273 (4)0.0313 (5)0.0001 (4)0.0016 (4)0.0009 (4)
Geometric parameters (Å, º) top
C1—C21.395 (6)C13—C181.387 (6)
C1—C61.402 (6)C13—P11.806 (4)
C1—P11.800 (4)C14—C151.400 (6)
C2—C31.394 (6)C14—H140.9300
C2—H20.9300C15—C161.363 (8)
C3—C41.355 (7)C15—H150.9300
C3—H30.9300C16—C171.381 (8)
C4—C51.384 (7)C16—H160.9300
C4—H40.9300C17—C181.386 (6)
C5—C61.387 (6)C17—H170.9300
C5—H50.9300C18—H180.9300
C6—H60.9300C19—C211.514 (6)
C7—C121.388 (6)C19—C201.523 (6)
C7—C81.400 (6)C19—P11.818 (4)
C7—P11.789 (4)C19—H190.9800
C8—C91.374 (7)C20—H20A0.9600
C8—H80.9300C20—H20B0.9600
C9—C101.394 (10)C20—H20C0.9600
C9—H90.9300C21—H21A0.9600
C10—C111.345 (10)C21—H21B0.9600
C10—H100.9300C21—H21C0.9600
C11—C121.377 (7)O1—H1O10.8522
C11—H110.9300O1—H2O10.8527
C12—H120.9300O2—H1O20.8515
C13—C141.382 (6)O2—H2O20.8512
C2—C1—C6119.4 (4)C13—C14—H14120.7
C2—C1—P1119.2 (3)C15—C14—H14120.7
C6—C1—P1121.1 (3)C16—C15—C14120.2 (5)
C3—C2—C1119.7 (5)C16—C15—H15119.9
C3—C2—H2120.2C14—C15—H15119.9
C1—C2—H2120.2C15—C16—C17121.1 (4)
C4—C3—C2120.2 (5)C15—C16—H16119.5
C4—C3—H3119.9C17—C16—H16119.5
C2—C3—H3119.9C16—C17—C18119.7 (5)
C3—C4—C5121.4 (4)C16—C17—H17120.1
C3—C4—H4119.3C18—C17—H17120.1
C5—C4—H4119.3C17—C18—C13119.2 (5)
C4—C5—C6119.5 (4)C17—C18—H18120.4
C4—C5—H5120.2C13—C18—H18120.4
C6—C5—H5120.2C21—C19—C20111.4 (4)
C5—C6—C1119.8 (4)C21—C19—P1110.5 (3)
C5—C6—H6120.1C20—C19—P1112.1 (3)
C1—C6—H6120.1C21—C19—H19107.6
C12—C7—C8118.9 (4)C20—C19—H19107.6
C12—C7—P1122.0 (3)P1—C19—H19107.6
C8—C7—P1118.7 (3)C19—C20—H20A109.5
C9—C8—C7120.8 (5)C19—C20—H20B109.5
C9—C8—H8119.6H20A—C20—H20B109.5
C7—C8—H8119.6C19—C20—H20C109.5
C8—C9—C10118.7 (6)H20A—C20—H20C109.5
C8—C9—H9120.7H20B—C20—H20C109.5
C10—C9—H9120.7C19—C21—H21A109.5
C11—C10—C9120.9 (5)C19—C21—H21B109.5
C11—C10—H10119.6H21A—C21—H21B109.5
C9—C10—H10119.6C19—C21—H21C109.5
C10—C11—C12121.1 (6)H21A—C21—H21C109.5
C10—C11—H11119.4H21B—C21—H21C109.5
C12—C11—H11119.4H1O1—O1—H2O198.0
C11—C12—C7119.6 (5)H1O2—O2—H2O298.0
C11—C12—H12120.2C7—P1—C1112.38 (19)
C7—C12—H12120.2C7—P1—C13109.67 (19)
C14—C13—C18121.2 (4)C1—P1—C13106.56 (17)
C14—C13—P1119.5 (3)C7—P1—C19107.68 (18)
C18—C13—P1118.8 (3)C1—P1—C19108.99 (19)
C13—C14—C15118.6 (5)C13—P1—C19111.62 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O1···Br1i0.852.863.701 (8)169
O1—H2O1···O20.852.202.960 (11)149
O2—H1O2···Br1ii0.852.683.526 (7)175
O2—H2O2···Br1iii0.852.813.598 (8)154
C19—H19···Br1iv0.982.763.723 (4)169
Symmetry codes: (i) −x+1/2, −y+1, z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+3/2, −y+1, z+1/2; (iv) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC21H22P+·Br−·H2O
Mr403.28
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)9.078 (5), 13.043 (5), 17.755 (5)
V (Å3)2102.3 (15)
Z4
Radiation typeMo Kα
µ (mm−1)2.04
Crystal size (mm)0.20 × 0.15 × 0.13
Data collection
DiffractometerBrucker APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.668, 0.688
No. of measured, independent and
observed [I > 2σ(I)] reflections		12177, 4250, 3331
Rint0.034
(sin θ/λ)max (Å−1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.140, 1.03
No. of reflections4250
No. of parameters228
No. of restraints6
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.82, −0.28
Absolute structureFlack (1983), 1799 Friedel pairs
Absolute structure parameter0.014 (13)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O1···Br1i0.852.863.701 (8)168.91
O1—H2O1···O20.852.202.960 (11)148.89
O2—H1O2···Br1ii0.852.683.526 (7)175.08
O2—H2O2···Br1iii0.852.813.598 (8)153.85
C19—H19···Br1iv0.982.763.723 (4)168.69
Symmetry codes: (i) −x+1/2, −y+1, z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+3/2, −y+1, z+1/2; (iv) x, y, z+1.
 

Acknowledgements

This work was supported by Shandong College research program (J11LB15) and the Young and Middle-aged Scientist Research Awards Foundation of Shandong Province (BS2010CL045).

References

First citationAlcock, N. W., Pennington, M. & Willey, G. R. (1985). Acta Cryst. C41, 1549–1550.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CSD CrossRef Web of Science Google Scholar
 First citationAsai, S., Nakamura, H., Tanabe, M. & Sakamoto, K. (1994). Ind. Eng. Chem. Res. 33, 1687–1691  CrossRef CAS Web of Science Google Scholar
 First citationBruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals 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

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ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3149
https://doi.org/10.1107/S1600536811044849
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