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

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COMMUNICATIONS
ISSN: 2056-9890

Iso­propyl 2,2-bis­­(4-bromo­phen­yl)-2-hy­dr­oxy­acetate

aScience and Engineering Faculty, Queensland University of Technology, GPO Box 2434, Brisbane, Queensland 4001, Australia
*Correspondence e-mail: g.smith@qut.edu.au

(Received 27 October 2012; accepted 28 October 2012; online 3 November 2012)

The title compound, C17H16Br2O3, which is a restricted commercial acaricide (common name bromo­propyl­ate), has two independent and conformationally similar mol­ecules in the asymmetric unit [dihedral angles between the planes of the two phenyl rings = 68.7 (4) and 77.4 (5)°]. The C atoms of the isopropyl group of one of the mol­ecules are disordered over two sites with occupancies of 0.638 (16) and 0.362 (16). Minor non-merohedral twinning was also present in the crystal. Inter­molecular O—H⋯O hydrogen-bonding inter­actions involving the hy­droxy groups and carboxyl O-atom acceptors give separate centrosymmetric homodimers through cyclic hydrogen-bonding motifs [graph set R22(10)].

Related literature

For background information on bromo­propyl­ate, see: O'Neil (2001[O'Neil, M. C. (2001). The Merck Index, 13th ed., p. 239. Whitehouse Station, NJ, USA: Merck & Co. Inc.]). For the structures of benzilic acid and an analogous benzilate ester, see: Qui et al. (2007[Qui, Y., Wang, K., Liu, Y., Deng, H., Sun, F. & Cai, Y. (2007). Inorg. Chim. Acta, 360, 1819-1824.]); Fu et al. (2006[Fu, D.-C., Sun, F.-X., Liu, Q. & Lv, H.-J. (2006). Acta Cryst. E62, o5284-o5285.]). For graph-set analysis, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]).

[Scheme 1]

Experimental

Crystal data
  • C17H16Br2O3

  • Mr = 428.10

  • Triclinic, [P \overline 1]

  • a = 10.2036 (6) Å

  • b = 10.2166 (6) Å

  • c = 17.6687 (13) Å

  • α = 83.775 (5)°

  • β = 73.346 (6)°

  • γ = 72.937 (5)°

  • V = 1686.4 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 4.82 mm−1

  • T = 200 K

  • 0.30 × 0.20 × 0.12 mm

Data collection
  • Oxford Diffraction Gemini-S CCD-detector diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]) Tmin = 0.581, Tmax = 0.980

  • 21160 measured reflections

  • 6627 independent reflections

  • 5435 reflections with I > 2σ(I)

  • Rint = 0.048

Refinement
  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 0.156

  • S = 1.08

  • 6627 reflections

  • 408 parameters

  • H-atom parameters constrained

  • Δρmax = 1.20 e Å−3

  • Δρmin = −1.14 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O11A—H11A⋯O22Ai 0.94 1.99 2.866 (6) 154
O11C—H11C⋯O22Cii 0.82 2.17 2.828 (6) 137
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+2, -y, -z.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) within WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.

Supporting information


Comment top

The title compound C17H16Br2O3, (common name bromopropylate) is the isopropyl ester of 4,4'-dibromobenzilic acid and is available for limited commercial use as a contact acaricide (Acarol, Neorol) (O'Neil, 2001). The structure of benzilic acid (Qui et al., 2007) and its 1-methylpiperidin-4-yl ester (Fu et al., 2006) have previously been reported.

In the structure of the title compound there are two independent and conformationally similar molecules in the asymmetric unit (Figs. 1, 2). The dihedral angles between the planes of the two phenyl rings in these molecules are 68.7 (4) and 77.4 (5)°. However, in one of the molecules the isopropyl group is disordered over two separate sites [C31A, C41A, C51A [S.O.F = 0.638 (16)] and C31E, C41E, C51E [S.O.F. = 0.362 (16)]. Minor non-merohedral twinning was also present in the crystal. Intermolecular hydrogen-bonding interactions involving the hydroxy groups and carboxyl O-atom acceptors (Table 1) give separate centrosymmetric homodimers through cyclic motifs [graph set R22(10) (Etter et al., 1990)] (Fig. 3). Other intramolecular aromatic C—H···O interactions are also present in the dimers as well as relatively short intermolecular Br···O interactions [Br4B···O11Aiii, 3.348 (4) Å; Br4C···O11Ciii, 3.389 (4) Å [for symmetry code (iii), x-1, y, z].

Related literature top

For background information on bromopropylate, see: O'Neil (2001). For the structures of benzilic acid and an analogous benzilate ester, see: Qui et al. (2007); Fu et al. (2006). For graph-set analysis, see: Etter et al. (1990).

Experimental top

The title compound bromopropylate was obtained as an analytical reference standard from the U.S. Environmental Protection Agency. Colourless crystal plates suitable for X-ray analysis were obtained by room temperature evaporation of a solution in ethanol.

Refinement top

Hydroxyl H-atoms were located in a difference-Fourier synthesis but were subsequently allowed to ride in the refinement with Uiso(H) = 1.2Ueq(O). Other H-atoms were included in the refinement at calculated positions [C—H = 0.93 Å (aromatic), 0.97 Å (methine) and 0.96 Å (methyl), with Uiso(H) = 1.2Ueq(aromatic or methine C) or 1.5Ueq(methyl C)], also using a riding-model approximation. Disorder was present in the C-atoms of the isopropyl group of one of the molecules and the occupancies were determined as 0.638 (16) [atoms C31A, C41A, C51A], and 0.362 (16) [atoms C31E, C41E, C51E]. Minor non-merohedral twinning was identified and handled in the refinement (BASF = 0.0779). The maximum difference electron density peak was 1.195 Å-3 (0.90 Å from Br4B).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. Molecular conformation and atom numbering scheme for molecule 1 of the two independent molecules in the asymmetric unit of the title compound, including the C atoms (C31E, C41E, C51E) of the disordered isopropyl group. Displacement ellipsoids are drawn at the 40% probability level.
[Figure 2] Fig. 2. Molecular conformation and atom numbering scheme for the second molecule in the asymmetric unit of the title compound, with displacement ellipsoids drawn at the 40% probability level.
[Figure 3] Fig. 3. A perspective view of the two hydrogen-bonded homodimeric units in the unit cell, viewed along a. The minor disorder component of the isopropyl group of the first molecule is not shown.
Isopropyl 2,2-bis(4-bromophenyl)-2-hydroxyacetate top
Crystal data top
C17H16Br2O3Z = 4
Mr = 428.10F(000) = 848
Triclinic, P1Dx = 1.686 Mg m3
Hall symbol: -P 1Melting point: 350 K
a = 10.2036 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.2166 (6) ÅCell parameters from 5077 reflections
c = 17.6687 (13) Åθ = 3.1–28.9°
α = 83.775 (5)°µ = 4.82 mm1
β = 73.346 (6)°T = 200 K
γ = 72.937 (5)°Block, colourless
V = 1686.4 (2) Å30.30 × 0.20 × 0.12 mm
Data collection top
Oxford Diffraction Gemini-S CCD-detector
diffractometer
6627 independent reflections
Radiation source: Enhance (Mo) X-ray source5435 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
Detector resolution: 16.077 pixels mm-1θmax = 26.0°, θmin = 3.1°
ω scansh = 1212
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
k = 1212
Tmin = 0.581, Tmax = 0.980l = 2121
21160 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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0571P)2 + 8.7092P]
where P = (Fo2 + 2Fc2)/3
6627 reflections(Δ/σ)max = 0.002
408 parametersΔρmax = 1.20 e Å3
0 restraintsΔρmin = 1.14 e Å3
Crystal data top
C17H16Br2O3γ = 72.937 (5)°
Mr = 428.10V = 1686.4 (2) Å3
Triclinic, P1Z = 4
a = 10.2036 (6) ÅMo Kα radiation
b = 10.2166 (6) ŵ = 4.82 mm1
c = 17.6687 (13) ÅT = 200 K
α = 83.775 (5)°0.30 × 0.20 × 0.12 mm
β = 73.346 (6)°
Data collection top
Oxford Diffraction Gemini-S CCD-detector
diffractometer
6627 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
5435 reflections with I > 2σ(I)
Tmin = 0.581, Tmax = 0.980Rint = 0.048
21160 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0550 restraints
wR(F2) = 0.156H-atom parameters constrained
S = 1.08Δρmax = 1.20 e Å3
6627 reflectionsΔρmin = 1.14 e Å3
408 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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)
Br4A0.89518 (9)1.30205 (7)0.27385 (4)0.0459 (3)
Br4B0.30004 (9)0.64421 (10)0.40830 (5)0.0564 (3)
O11A0.9752 (4)0.6496 (4)0.3992 (2)0.0296 (12)
O21A0.7448 (6)0.8256 (5)0.5730 (3)0.0483 (18)
O22A0.9228 (6)0.6320 (5)0.5558 (3)0.0418 (17)
C1A0.8626 (6)0.8855 (6)0.4047 (3)0.0237 (17)
C1B0.7154 (7)0.7172 (6)0.4347 (3)0.0267 (17)
C2A0.8808 (7)0.9874 (7)0.4424 (4)0.0324 (19)
C2B0.5880 (8)0.8199 (7)0.4497 (5)0.043 (3)
C3A0.8907 (7)1.1118 (7)0.4037 (4)0.034 (2)
C3B0.4654 (8)0.7966 (8)0.4439 (5)0.045 (3)
C4A0.8842 (7)1.1319 (6)0.3272 (4)0.0281 (17)
C4B0.4695 (8)0.6706 (8)0.4218 (4)0.040 (3)
C5A0.8678 (8)1.0319 (7)0.2868 (4)0.038 (2)
C5B0.5937 (8)0.5666 (7)0.4060 (4)0.036 (2)
C6A0.8579 (8)0.9096 (7)0.3262 (4)0.036 (2)
C6B0.7167 (8)0.5900 (7)0.4130 (4)0.035 (2)
C11A0.8518 (6)0.7449 (6)0.4404 (4)0.0260 (17)
C21A0.8464 (7)0.7282 (6)0.5296 (4)0.0310 (19)
C31A0.7366 (17)0.8166 (16)0.6594 (8)0.040 (4)0.638 (16)
C41A0.719 (3)0.9601 (19)0.6863 (12)0.056 (6)0.638 (16)
C51A0.609 (2)0.7606 (19)0.6920 (10)0.079 (7)0.638 (16)
C51E0.525 (4)0.828 (4)0.6798 (19)0.079 (7)0.362 (16)
C31E0.675 (3)0.802 (3)0.6601 (17)0.040 (4)0.362 (16)
C41E0.723 (5)0.904 (4)0.697 (2)0.056 (6)0.362 (16)
Br4C0.18617 (7)0.14249 (8)0.07253 (5)0.0447 (3)
Br4D0.66910 (9)0.77309 (7)0.21608 (4)0.0419 (2)
O11C0.8480 (4)0.1314 (4)0.0961 (2)0.0261 (12)
O21C0.8124 (4)0.3361 (4)0.0781 (2)0.0285 (12)
O22C0.9644 (5)0.1328 (4)0.0599 (2)0.0317 (12)
C1C0.6305 (6)0.2050 (6)0.0518 (3)0.0208 (17)
C1D0.7444 (6)0.3692 (6)0.0908 (3)0.0208 (17)
C2C0.5973 (7)0.0877 (6)0.0871 (3)0.0260 (17)
C2D0.8500 (7)0.4364 (6)0.0735 (4)0.0282 (17)
C3C0.4664 (7)0.0675 (6)0.0915 (4)0.0288 (17)
C3D0.8284 (7)0.5557 (6)0.1114 (4)0.0300 (17)
C4C0.3697 (7)0.1655 (7)0.0614 (4)0.0302 (17)
C4D0.7019 (7)0.6066 (6)0.1669 (3)0.0272 (19)
C5C0.4017 (7)0.2818 (7)0.0237 (4)0.034 (2)
C5D0.5988 (7)0.5403 (6)0.1858 (4)0.0301 (17)
C6C0.5316 (7)0.3007 (6)0.0177 (4)0.0298 (19)
C6D0.6194 (7)0.4215 (6)0.1476 (4)0.0296 (17)
C11C0.7712 (6)0.2330 (6)0.0516 (3)0.0231 (17)
C21C0.8619 (6)0.2286 (6)0.0351 (3)0.0222 (17)
C31C0.8718 (7)0.3287 (7)0.1646 (4)0.0315 (19)
C41C0.8017 (9)0.2421 (9)0.1959 (5)0.050 (3)
C51C0.8390 (10)0.4762 (8)0.1954 (4)0.054 (3)
H2A0.886500.973000.494400.0390*
H5A0.863601.046600.234600.0460*
H5B0.595300.481600.390900.0430*
H6A0.847800.841000.299600.0430*
H6B0.801100.519800.403000.0420*
H11A0.993000.567600.429500.0440*
H31A0.822200.751600.669500.0480*0.638 (16)
H41A0.805800.985500.664000.0850*0.638 (16)
H42A0.696700.959700.743000.0850*0.638 (16)
H43A0.643001.024800.669000.0850*0.638 (16)
H51A0.628900.672000.670900.1190*0.638 (16)
H52A0.527900.821600.677200.1190*0.638 (16)
H53A0.587900.752900.748600.1190*0.638 (16)
H2B0.585600.905800.464000.0520*
H3A0.901801.180500.429800.0400*
H3B0.380200.865800.454900.0550*
H31E0.717400.708200.676800.0480*0.362 (16)
H41E0.824800.875600.686200.0850*0.362 (16)
H42E0.680600.906200.752600.0850*0.362 (16)
H43E0.693800.993600.673500.0850*0.362 (16)
H51E0.501100.752900.664200.1190*0.362 (16)
H52E0.485400.910500.652600.1190*0.362 (16)
H53E0.486300.839400.735800.1190*0.362 (16)
H2C0.662900.021700.108200.0310*
H2D0.935800.401100.036200.0340*
H3C0.444800.012400.114800.0350*
H3D0.899000.601000.099400.0360*
H5C0.335700.347000.002500.0410*
H5D0.514500.574500.224300.0360*
H6C0.554800.377700.009300.0350*
H6D0.548400.376700.160300.0350*
H11C0.863500.055700.078400.0390*
H31C0.975000.287400.177600.0440*
H41C0.825900.150200.174900.0750*
H42C0.834500.241100.252500.0750*
H43C0.700300.280100.180100.0750*
H51C0.886400.526100.174300.0810*
H52C0.738200.517700.179300.0810*
H53C0.871700.478100.252000.0810*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br4A0.0662 (5)0.0316 (4)0.0400 (4)0.0165 (3)0.0145 (4)0.0082 (3)
Br4B0.0428 (4)0.0875 (7)0.0494 (5)0.0334 (4)0.0163 (4)0.0080 (4)
O11A0.028 (2)0.030 (2)0.023 (2)0.0009 (18)0.0006 (18)0.0052 (17)
O21A0.067 (4)0.035 (3)0.019 (2)0.010 (2)0.000 (2)0.0008 (19)
O22A0.054 (3)0.034 (3)0.033 (3)0.002 (2)0.020 (2)0.001 (2)
C1A0.021 (3)0.030 (3)0.016 (3)0.003 (2)0.003 (2)0.000 (2)
C1B0.028 (3)0.029 (3)0.019 (3)0.007 (3)0.001 (3)0.000 (2)
C2A0.043 (4)0.035 (3)0.025 (3)0.014 (3)0.015 (3)0.000 (3)
C2B0.032 (4)0.035 (4)0.056 (5)0.001 (3)0.007 (3)0.013 (3)
C3A0.044 (4)0.034 (4)0.031 (3)0.017 (3)0.015 (3)0.003 (3)
C3B0.026 (4)0.054 (5)0.049 (5)0.003 (3)0.005 (3)0.007 (4)
C4A0.035 (3)0.024 (3)0.027 (3)0.009 (3)0.011 (3)0.002 (2)
C4B0.038 (4)0.057 (5)0.031 (4)0.024 (3)0.013 (3)0.013 (3)
C5A0.055 (5)0.041 (4)0.022 (3)0.014 (3)0.014 (3)0.001 (3)
C5B0.043 (4)0.033 (4)0.037 (4)0.016 (3)0.015 (3)0.004 (3)
C6A0.058 (5)0.032 (3)0.023 (3)0.017 (3)0.015 (3)0.003 (3)
C6B0.039 (4)0.028 (3)0.038 (4)0.011 (3)0.010 (3)0.006 (3)
C11A0.025 (3)0.024 (3)0.024 (3)0.000 (2)0.005 (3)0.003 (2)
C21A0.040 (4)0.020 (3)0.030 (3)0.006 (3)0.007 (3)0.001 (2)
C31A0.041 (10)0.043 (6)0.018 (4)0.004 (7)0.007 (7)0.010 (4)
C41A0.080 (8)0.061 (14)0.020 (7)0.016 (12)0.007 (6)0.004 (9)
C51A0.097 (15)0.070 (12)0.052 (8)0.030 (9)0.012 (9)0.011 (8)
C51E0.097 (15)0.070 (12)0.052 (8)0.030 (9)0.012 (9)0.011 (8)
C31E0.041 (10)0.043 (6)0.018 (4)0.004 (7)0.007 (7)0.010 (4)
C41E0.080 (8)0.061 (14)0.020 (7)0.016 (12)0.007 (6)0.004 (9)
Br4C0.0290 (4)0.0519 (5)0.0557 (5)0.0159 (3)0.0076 (3)0.0092 (3)
Br4D0.0655 (5)0.0264 (3)0.0359 (4)0.0129 (3)0.0150 (4)0.0055 (3)
O11C0.030 (2)0.022 (2)0.026 (2)0.0013 (17)0.0136 (19)0.0005 (16)
O21C0.031 (2)0.027 (2)0.020 (2)0.0001 (18)0.0045 (18)0.0013 (17)
O22C0.033 (2)0.029 (2)0.026 (2)0.0002 (19)0.0057 (19)0.0008 (18)
C1C0.024 (3)0.020 (3)0.018 (3)0.005 (2)0.006 (2)0.001 (2)
C1D0.022 (3)0.021 (3)0.018 (3)0.005 (2)0.005 (2)0.002 (2)
C2C0.030 (3)0.020 (3)0.024 (3)0.002 (2)0.006 (3)0.001 (2)
C2D0.022 (3)0.033 (3)0.029 (3)0.008 (3)0.005 (3)0.002 (3)
C3C0.035 (3)0.023 (3)0.028 (3)0.014 (3)0.001 (3)0.002 (2)
C3D0.029 (3)0.033 (3)0.030 (3)0.015 (3)0.006 (3)0.003 (3)
C4C0.030 (3)0.035 (3)0.024 (3)0.008 (3)0.003 (3)0.008 (3)
C4D0.042 (4)0.017 (3)0.022 (3)0.005 (3)0.011 (3)0.000 (2)
C5C0.028 (3)0.036 (4)0.042 (4)0.007 (3)0.018 (3)0.000 (3)
C5D0.023 (3)0.034 (3)0.029 (3)0.002 (3)0.004 (3)0.007 (3)
C6C0.031 (3)0.023 (3)0.035 (4)0.008 (3)0.010 (3)0.006 (2)
C6D0.026 (3)0.033 (3)0.028 (3)0.009 (3)0.003 (3)0.003 (3)
C11C0.024 (3)0.020 (3)0.024 (3)0.003 (2)0.009 (2)0.003 (2)
C21C0.022 (3)0.019 (3)0.026 (3)0.005 (2)0.008 (2)0.000 (2)
C31C0.029 (3)0.038 (4)0.021 (3)0.004 (3)0.003 (3)0.002 (3)
C41C0.059 (5)0.060 (5)0.038 (4)0.016 (4)0.022 (4)0.002 (4)
C51C0.071 (6)0.049 (5)0.033 (4)0.014 (4)0.009 (4)0.016 (3)
Geometric parameters (Å, º) top
Br4A—C4A1.903 (6)C41A—H41A0.9600
Br4B—C4B1.909 (9)C41A—H42A0.9600
Br4C—C4C1.907 (8)C41A—H43A0.9600
Br4D—C4D1.892 (6)C41E—H41E0.9600
O11A—C11A1.404 (7)C41E—H42E0.9500
O21A—C31E1.53 (3)C41E—H43E0.9600
O21A—C31A1.499 (15)C51A—H51A0.9600
O21A—C21A1.326 (8)C51A—H53A0.9600
O22A—C21A1.203 (8)C51A—H52A0.9600
O11A—H11A0.9400C51E—H51E0.9600
O11C—C11C1.417 (7)C51E—H53E0.9600
O21C—C31C1.475 (8)C51E—H52E0.9600
O21C—C21C1.324 (7)C1C—C2C1.377 (8)
O22C—C21C1.214 (7)C1C—C6C1.407 (9)
O11C—H11C0.8200C1C—C11C1.543 (9)
C1A—C11A1.526 (8)C1D—C6D1.379 (9)
C1A—C6A1.394 (9)C1D—C11C1.539 (8)
C1A—C2A1.377 (9)C1D—C2D1.388 (10)
C1B—C2B1.387 (10)C2C—C3C1.390 (11)
C1B—C11A1.531 (10)C2D—C3D1.385 (9)
C1B—C6B1.390 (9)C3C—C4C1.365 (10)
C2A—C3A1.393 (10)C3D—C4D1.375 (9)
C2B—C3B1.373 (12)C4C—C5C1.376 (10)
C3A—C4A1.363 (10)C4D—C5D1.358 (10)
C3B—C4B1.371 (11)C5C—C6C1.368 (11)
C4A—C5A1.381 (10)C5D—C6D1.386 (9)
C4B—C5B1.373 (11)C11C—C21C1.544 (7)
C5A—C6A1.379 (10)C31C—C41C1.518 (12)
C5B—C6B1.385 (12)C31C—C51C1.520 (10)
C11A—C21A1.554 (10)C2C—H2C0.9300
C31A—C51A1.51 (3)C2D—H2D0.9300
C31A—C41A1.54 (3)C3C—H3C0.9300
C31E—C41E1.54 (5)C3D—H3D0.9300
C31E—C51E1.42 (5)C5C—H5C0.9300
C2A—H2A0.9300C5D—H5D0.9300
C2B—H2B0.9300C6C—H6C0.9300
C3A—H3A0.9300C6D—H6D0.9300
C3B—H3B0.9300C31C—H31C0.9800
C5A—H5A0.9300C41C—H41C0.9600
C5B—H5B0.9300C41C—H42C0.9600
C6A—H6A0.9300C41C—H43C0.9600
C6B—H6B0.9300C51C—H51C0.9600
C31A—H31A0.9800C51C—H52C0.9600
C31E—H31E0.9800C51C—H53C0.9600
C21A—O21A—C31A115.5 (8)H52A—C51A—H53A109.00
C21A—O21A—C31E122.2 (12)H51A—C51A—H52A109.00
C11A—O11A—H11A110.00H51A—C51A—H53A109.00
C21C—O21C—C31C117.2 (4)C31A—C51A—H51A110.00
C11C—O11C—H11C110.00C31A—C51A—H53A110.00
C2A—C1A—C6A117.9 (6)C31E—C51E—H53E110.00
C2A—C1A—C11A125.7 (5)C31E—C51E—H51E110.00
C6A—C1A—C11A116.3 (5)H51E—C51E—H53E110.00
C2B—C1B—C6B118.5 (7)H52E—C51E—H53E109.00
C2B—C1B—C11A120.5 (6)H51E—C51E—H52E109.00
C6B—C1B—C11A121.0 (6)C31E—C51E—H52E109.00
C1A—C2A—C3A120.9 (6)C2C—C1C—C6C118.6 (6)
C1B—C2B—C3B121.0 (7)C6C—C1C—C11C120.6 (5)
C2A—C3A—C4A119.4 (6)C2C—C1C—C11C120.8 (6)
C2B—C3B—C4B119.5 (8)C2D—C1D—C11C120.3 (5)
Br4A—C4A—C3A120.0 (5)C6D—C1D—C11C120.7 (6)
Br4A—C4A—C5A118.4 (5)C2D—C1D—C6D118.9 (6)
C3A—C4A—C5A121.7 (6)C1C—C2C—C3C120.4 (6)
C3B—C4B—C5B121.3 (8)C1D—C2D—C3D120.4 (6)
Br4B—C4B—C3B118.6 (6)C2C—C3C—C4C119.7 (6)
Br4B—C4B—C5B120.1 (6)C2D—C3D—C4D119.5 (7)
C4A—C5A—C6A118.0 (6)Br4C—C4C—C5C119.2 (6)
C4B—C5B—C6B119.0 (7)C3C—C4C—C5C121.1 (7)
C1A—C6A—C5A122.1 (7)Br4C—C4C—C3C119.7 (5)
C1B—C6B—C5B120.7 (7)Br4D—C4D—C3D119.7 (5)
C1A—C11A—C1B111.1 (5)C3D—C4D—C5D120.8 (6)
C1A—C11A—C21A113.8 (5)Br4D—C4D—C5D119.5 (5)
O11A—C11A—C21A107.9 (5)C4C—C5C—C6C119.4 (7)
O11A—C11A—C1A106.2 (5)C4D—C5D—C6D119.9 (6)
O11A—C11A—C1B112.5 (5)C1C—C6C—C5C120.8 (6)
C1B—C11A—C21A105.4 (5)C1D—C6D—C5D120.5 (7)
O21A—C21A—O22A124.5 (6)O11C—C11C—C1C111.5 (5)
O21A—C21A—C11A113.1 (5)O11C—C11C—C1D105.3 (4)
O22A—C21A—C11A122.3 (6)C1C—C11C—C1D111.6 (5)
C41A—C31A—C51A115.7 (16)C1C—C11C—C21C107.1 (5)
O21A—C31A—C41A108.3 (12)O11C—C11C—C21C108.4 (5)
O21A—C31A—C51A100.3 (12)C1D—C11C—C21C112.9 (5)
O21A—C31E—C41E100 (2)O21C—C21C—C11C112.9 (5)
O21A—C31E—C51E115 (2)O22C—C21C—C11C122.0 (5)
C41E—C31E—C51E113 (3)O21C—C21C—O22C125.1 (5)
C3A—C2A—H2A120.00O21C—C31C—C51C105.5 (5)
C1A—C2A—H2A120.00C41C—C31C—C51C112.9 (7)
C3B—C2B—H2B120.00O21C—C31C—C41C108.4 (6)
C1B—C2B—H2B119.00C1C—C2C—H2C120.00
C2A—C3A—H3A120.00C3C—C2C—H2C120.00
C4A—C3A—H3A120.00C1D—C2D—H2D120.00
C4B—C3B—H3B120.00C3D—C2D—H2D120.00
C2B—C3B—H3B120.00C2C—C3C—H3C120.00
C6A—C5A—H5A121.00C4C—C3C—H3C120.00
C4A—C5A—H5A121.00C2D—C3D—H3D120.00
C6B—C5B—H5B120.00C4D—C3D—H3D120.00
C4B—C5B—H5B121.00C4C—C5C—H5C120.00
C1A—C6A—H6A119.00C6C—C5C—H5C120.00
C5A—C6A—H6A119.00C4D—C5D—H5D120.00
C1B—C6B—H6B120.00C6D—C5D—H5D120.00
C5B—C6B—H6B120.00C1C—C6C—H6C120.00
C51A—C31A—H31A111.00C5C—C6C—H6C120.00
O21A—C31A—H31A111.00C1D—C6D—H6D120.00
C41A—C31A—H31A111.00C5D—C6D—H6D120.00
C51E—C31E—H31E109.00O21C—C31C—H31C110.00
C41E—C31E—H31E110.00C41C—C31C—H31C110.00
O21A—C31E—H31E110.00C51C—C31C—H31C110.00
C31A—C41A—H43A109.00C31C—C41C—H41C110.00
H41A—C41A—H42A109.00C31C—C41C—H42C110.00
H41A—C41A—H43A110.00C31C—C41C—H43C109.00
C31A—C41A—H42A109.00H41C—C41C—H42C109.00
H42A—C41A—H43A109.00H41C—C41C—H43C109.00
C31A—C41A—H41A110.00H42C—C41C—H43C109.00
H41E—C41E—H42E110.00C31C—C51C—H51C109.00
C31E—C41E—H42E110.00C31C—C51C—H52C109.00
C31E—C41E—H43E109.00C31C—C51C—H53C110.00
H42E—C41E—H43E110.00H51C—C51C—H52C109.00
C31E—C41E—H41E109.00H51C—C51C—H53C109.00
H41E—C41E—H43E109.00H52C—C51C—H53C109.00
C31A—C51A—H52A110.00
C31A—O21A—C21A—O22A5.0 (13)C1A—C11A—C21A—O22A130.0 (7)
C31A—O21A—C21A—C11A178.7 (9)O11A—C11A—C21A—O21A171.2 (6)
C21A—O21A—C31A—C41A134.8 (15)O11A—C11A—C21A—O22A12.4 (9)
C21A—O21A—C31A—C51A103.6 (12)C1A—C11A—C21A—O21A53.6 (8)
C31C—O21C—C21C—O22C10.2 (9)C6C—C1C—C2C—C3C2.5 (8)
C31C—O21C—C21C—C11C167.4 (5)C11C—C1C—C2C—C3C175.8 (5)
C21C—O21C—C31C—C41C78.6 (7)C2C—C1C—C6C—C5C4.0 (9)
C21C—O21C—C31C—C51C160.4 (6)C11C—C1C—C6C—C5C174.4 (6)
C2A—C1A—C11A—O11A112.2 (7)C2C—C1C—C11C—O11C4.6 (7)
C2A—C1A—C11A—C1B125.2 (7)C2C—C1C—C11C—C1D122.1 (5)
C2A—C1A—C11A—C21A6.4 (10)C2C—C1C—C11C—C21C113.9 (6)
C6A—C1A—C2A—C3A1.5 (11)C6C—C1C—C11C—O11C173.7 (5)
C11A—C1A—C2A—C3A179.4 (7)C6C—C1C—C11C—C1D56.2 (7)
C2A—C1A—C6A—C5A1.4 (11)C6C—C1C—C11C—C21C67.9 (7)
C11A—C1A—C6A—C5A179.4 (7)C6D—C1D—C2D—C3D1.5 (9)
C6A—C1A—C11A—C21A175.7 (6)C11C—C1D—C2D—C3D177.1 (6)
C6A—C1A—C11A—O11A65.7 (7)C2D—C1D—C6D—C5D1.0 (10)
C6A—C1A—C11A—C1B56.9 (8)C11C—C1D—C6D—C5D176.5 (6)
C2B—C1B—C6B—C5B0.4 (10)C2D—C1D—C11C—O11C81.2 (6)
C2B—C1B—C11A—C1A41.2 (8)C2D—C1D—C11C—C1C157.7 (5)
C11A—C1B—C6B—C5B178.4 (6)C2D—C1D—C11C—C21C37.0 (8)
C2B—C1B—C11A—O11A160.1 (6)C6D—C1D—C11C—O11C94.2 (7)
C11A—C1B—C2B—C3B179.3 (7)C6D—C1D—C11C—C1C26.9 (7)
C6B—C1B—C11A—C21A98.7 (6)C6D—C1D—C11C—C21C147.6 (6)
C2B—C1B—C11A—C21A82.5 (7)C1C—C2C—C3C—C4C0.8 (9)
C6B—C1B—C11A—O11A18.7 (8)C1D—C2D—C3D—C4D0.6 (10)
C6B—C1B—C11A—C1A137.6 (6)C2C—C3C—C4C—Br4C176.6 (5)
C6B—C1B—C2B—C3B0.5 (11)C2C—C3C—C4C—C5C2.8 (10)
C1A—C2A—C3A—C4A0.9 (11)C2D—C3D—C4D—Br4D177.7 (5)
C1B—C2B—C3B—C4B1.0 (12)C2D—C3D—C4D—C5D1.0 (10)
C2A—C3A—C4A—Br4A179.2 (6)Br4C—C4C—C5C—C6C178.0 (5)
C2A—C3A—C4A—C5A0.1 (12)C3C—C4C—C5C—C6C1.3 (10)
C2B—C3B—C4B—C5B0.6 (12)Br4D—C4D—C5D—C6D177.2 (5)
C2B—C3B—C4B—Br4B176.4 (6)C3D—C4D—C5D—C6D1.5 (10)
C3A—C4A—C5A—C6A0.1 (12)C4C—C5C—C6C—C1C2.1 (10)
Br4A—C4A—C5A—C6A179.1 (6)C4D—C5D—C6D—C1D0.5 (10)
C3B—C4B—C5B—C6B0.3 (11)O11C—C11C—C21C—O21C167.6 (5)
Br4B—C4B—C5B—C6B177.3 (5)O11C—C11C—C21C—O22C14.7 (8)
C4A—C5A—C6A—C1A0.6 (12)C1C—C11C—C21C—O21C71.9 (6)
C4B—C5B—C6B—C1B0.8 (10)C1C—C11C—C21C—O22C105.7 (7)
C1B—C11A—C21A—O21A68.3 (7)C1D—C11C—C21C—O21C51.3 (7)
C1B—C11A—C21A—O22A108.1 (8)C1D—C11C—C21C—O22C131.0 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O11A—H11A···O22A0.942.252.660 (6)105
O11A—H11A···O22Ai0.941.992.866 (6)154
O11C—H11C···O22Cii0.822.172.828 (6)137
C2A—H2A···O21A0.932.442.944 (9)114
C2C—H2C···O11C0.932.412.773 (9)103
C6A—H6A···Br4D0.932.913.709 (8)144
C6B—H6B···O11A0.932.492.816 (10)101
C6C—H6C···O21C0.932.492.983 (8)113
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+2, y, z.

Experimental details

Crystal data
Chemical formulaC17H16Br2O3
Mr428.10
Crystal system, space groupTriclinic, P1
Temperature (K)200
a, b, c (Å)10.2036 (6), 10.2166 (6), 17.6687 (13)
α, β, γ (°)83.775 (5), 73.346 (6), 72.937 (5)
V3)1686.4 (2)
Z4
Radiation typeMo Kα
µ (mm1)4.82
Crystal size (mm)0.30 × 0.20 × 0.12
Data collection
DiffractometerOxford Diffraction Gemini-S CCD-detector
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2012)
Tmin, Tmax0.581, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections
21160, 6627, 5435
Rint0.048
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.156, 1.08
No. of reflections6627
No. of parameters408
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.20, 1.14

Computer programs: CrysAlis PRO (Agilent, 2012), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O11A—H11A···O22Ai0.941.992.866 (6)154
O11C—H11C···O22Cii0.822.172.828 (6)137
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+2, y, z.
 

Acknowledgements

The author acknowledges financial support from the Australian Research Council and the Science and Engineering Faculty and the University Library, Queensland University of Technology.

References

First citationAgilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.
First citationAltomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350.  CrossRef Web of Science IUCr Journals
First citationEtter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262.  CrossRef CAS Web of Science IUCr Journals
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals
First citationFu, D.-C., Sun, F.-X., Liu, Q. & Lv, H.-J. (2006). Acta Cryst. E62, o5284–o5285.  Web of Science CSD CrossRef IUCr Journals
First citationO'Neil, M. C. (2001). The Merck Index, 13th ed., p. 239. Whitehouse Station, NJ, USA: Merck & Co. Inc.
First citationQui, Y., Wang, K., Liu, Y., Deng, H., Sun, F. & Cai, Y. (2007). Inorg. Chim. Acta, 360, 1819–1824.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals

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