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Enantiomers of the title compound, C10H17BrO3, form hydrogen-bonded centrosymmetric dimers, where the carb­oxy H atom serves as donor and the C=O group of a neighbouring mol­ecule acts as acceptor. The proximity of two axial methyl substituents causes distortions of the tetra­hydro­pyran chair conformation, which are evident from the magnitude of the endocyclic bond angle at the O atom and the values of the endocyclic torsion angles.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806012499/fl2009sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806012499/fl2009Isup2.hkl
Contains datablock I

CCDC reference: 608327

Key indicators

  • Single-crystal X-ray study
  • T = 299 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.043
  • wR factor = 0.135
  • Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.97 PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.80 mm PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT731_ALERT_1_C Bond Calc 0.82(4), Rep 0.814(10) ...... 4.00 su-Rat O2 -H2 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.82(4), Rep 0.814(10) ...... 4.00 su-Rat O2 -H2 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 1.83(4), Rep 1.832(12) ...... 3.33 su-Rat H2 -O3 1.555 5.566
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 Diffractometer Control Software (Enraf–Nonius, 1993); cell refinement: CAD-4 Diffractometer Control Software; data reduction: CAD-4 Diffractometer Control Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON2002 (Spek, 2003) and ORTEP-3 (Farrugia, 1997, 2005); software used to prepare material for publication: SHELXL97.

5-cis-Bromo-2,2,6,6-tetramethyltetrahydropyran-3-carboxylic acid top
Crystal data top
C10H17BrO3Dx = 1.489 Mg m3
Mr = 265.15Melting point: 407 K
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 30.539 (1) ÅCell parameters from 25 reflections
b = 10.051 (1) Åθ = 4.1–12.3°
c = 7.748 (1) ŵ = 3.46 mm1
β = 95.74 (1)°T = 299 K
V = 2366.3 (4) Å3Needle, colourless
Z = 80.80 × 0.33 × 0.08 mm
F(000) = 1088
Data collection top
Enraf–Nonius CAD-4
diffractometer
1596 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
Graphite monochromatorθmax = 26.0°, θmin = 1.3°
ω/2θ scansh = 3737
Absorption correction: ψ scan
(North et al., 1968)
k = 120
Tmin = 0.169, Tmax = 0.782l = 91
2604 measured reflections3 standard reflections every 120 min
2328 independent reflections intensity decay: 0.1%
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0793P)2 + 3.5651P]
where P = (Fo2 + 2Fc2)/3
2328 reflections(Δ/σ)max = 0.005
134 parametersΔρmax = 0.94 e Å3
1 restraintΔρmin = 0.90 e Å3
Special details top

Experimental. 1H NMR (CDCl3, 400 MHz): δ 1.32 (s, 3H), 1.33 (s, 3H), 1.36 (s, 3H), 1.44 (s, 3H), 2.30 (dt, Jd = 13.3 Hz, Jt = 3.9 Hz, 1H), 2.52 (q, J = 13.3 Hz, 1H), 2.69 (dd, J = 3.9 and 13.3 Hz, 1H), 3.90 (dd, J = 3.9 and 13.3 Hz, 1H). 13C NMR (CDCl3, 63 MHz): δ 23.0, 24.0, 30.8, 30.9, 31.9, 53.7, 55.7, 73.6, 75.6, 177.0.

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C20.09472 (13)0.8108 (3)0.5259 (5)0.0425 (8)
C30.07493 (12)0.7306 (4)0.6705 (5)0.0403 (8)
H30.05990.79360.74080.048*
C40.11058 (13)0.6604 (4)0.7909 (5)0.0456 (9)
H4A0.09740.61970.88670.055*
H4B0.12410.59080.72760.055*
C50.14529 (12)0.7598 (4)0.8600 (5)0.0419 (8)
H50.13080.82800.92450.050*
C60.16739 (12)0.8296 (3)0.7160 (5)0.0411 (8)
C70.19730 (14)0.7407 (5)0.6197 (6)0.0581 (11)
H7A0.18310.65660.59520.070*
H7B0.22460.72690.69040.070*
H7C0.20300.78270.51290.070*
C80.19314 (14)0.9502 (4)0.7861 (6)0.0534 (10)
H8A0.21750.92190.86560.064*
H8B0.17431.00710.84520.064*
H8C0.20390.99810.69180.064*
C90.10740 (17)0.7207 (5)0.3791 (6)0.0646 (12)
H9A0.08120.69090.31110.077*
H9B0.12350.64520.42770.077*
H9C0.12540.76970.30670.077*
C100.06341 (16)0.9176 (5)0.4515 (6)0.0648 (13)
H10A0.05620.97570.54290.078*
H10B0.03700.87690.39810.078*
H10C0.07710.96790.36640.078*
C110.04133 (12)0.6300 (4)0.5972 (5)0.0424 (8)
O10.13141 (8)0.8876 (2)0.6032 (3)0.0419 (6)
O20.00411 (10)0.6809 (3)0.5287 (5)0.0623 (8)
H20.0110 (15)0.619 (4)0.489 (6)0.075*
O30.04830 (9)0.5108 (3)0.6033 (4)0.0576 (8)
Br10.188211 (15)0.66752 (5)1.02415 (6)0.0655 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.046 (2)0.0416 (19)0.0392 (18)0.0098 (16)0.0013 (16)0.0003 (15)
C30.0348 (18)0.0428 (19)0.0424 (19)0.0034 (15)0.0004 (15)0.0000 (16)
C40.0398 (19)0.048 (2)0.048 (2)0.0029 (16)0.0005 (16)0.0100 (17)
C50.0360 (18)0.047 (2)0.0419 (19)0.0022 (16)0.0019 (15)0.0015 (16)
C60.0361 (18)0.0426 (19)0.0439 (19)0.0031 (15)0.0008 (15)0.0019 (16)
C70.051 (2)0.059 (3)0.066 (3)0.002 (2)0.016 (2)0.006 (2)
C80.047 (2)0.051 (2)0.060 (2)0.0097 (18)0.0046 (19)0.0021 (19)
C90.077 (3)0.077 (3)0.042 (2)0.026 (3)0.013 (2)0.016 (2)
C100.066 (3)0.060 (3)0.063 (3)0.013 (2)0.021 (2)0.019 (2)
C110.038 (2)0.044 (2)0.045 (2)0.0042 (15)0.0007 (16)0.0039 (16)
O10.0434 (14)0.0375 (12)0.0429 (14)0.0084 (11)0.0050 (11)0.0020 (11)
O20.0427 (16)0.0486 (16)0.091 (2)0.0033 (12)0.0175 (16)0.0022 (15)
O30.0478 (16)0.0431 (16)0.078 (2)0.0059 (13)0.0118 (14)0.0024 (14)
Br10.0508 (3)0.0771 (4)0.0647 (3)0.0000 (2)0.0140 (2)0.0209 (2)
Geometric parameters (Å, º) top
C2—O11.441 (4)C7—H7A0.9600
C2—C101.513 (6)C7—H7B0.9600
C2—C91.534 (6)C7—H7C0.9600
C2—C31.551 (5)C8—H8A0.9600
C3—C111.510 (5)C8—H8B0.9600
C3—C41.533 (5)C8—H8C0.9600
C3—H30.9800C9—H9A0.9600
C4—C51.515 (5)C9—H9B0.9600
C4—H4A0.9700C9—H9C0.9600
C4—H4B0.9700C10—H10A0.9600
C5—C61.531 (5)C10—H10B0.9600
C5—Br11.966 (3)C10—H10C0.9600
C5—H50.9800C11—O31.216 (5)
C6—O11.455 (4)C11—O21.310 (5)
C6—C81.516 (5)O2—H20.814 (10)
C6—C71.525 (5)
O1—C2—C10102.4 (3)C6—C7—H7A109.5
O1—C2—C9112.4 (3)C6—C7—H7B109.5
C10—C2—C9109.5 (4)H7A—C7—H7B109.5
O1—C2—C3108.8 (3)C6—C7—H7C109.5
C10—C2—C3111.5 (3)H7A—C7—H7C109.5
C9—C2—C3112.0 (3)H7B—C7—H7C109.5
C11—C3—C4109.6 (3)C6—C8—H8A109.5
C11—C3—C2112.1 (3)C6—C8—H8B109.5
C4—C3—C2112.0 (3)H8A—C8—H8B109.5
C11—C3—H3107.7C6—C8—H8C109.5
C4—C3—H3107.7H8A—C8—H8C109.5
C2—C3—H3107.7H8B—C8—H8C109.5
C5—C4—C3110.0 (3)C2—C9—H9A109.5
C5—C4—H4A109.7C2—C9—H9B109.5
C3—C4—H4A109.7H9A—C9—H9B109.5
C5—C4—H4B109.7C2—C9—H9C109.5
C3—C4—H4B109.7H9A—C9—H9C109.5
H4A—C4—H4B108.2H9B—C9—H9C109.5
C4—C5—C6112.9 (3)C2—C10—H10A109.5
C4—C5—Br1108.4 (2)C2—C10—H10B109.5
C6—C5—Br1112.0 (2)H10A—C10—H10B109.5
C4—C5—H5107.8C2—C10—H10C109.5
C6—C5—H5107.8H10A—C10—H10C109.5
Br1—C5—H5107.8H10B—C10—H10C109.5
O1—C6—C8103.2 (3)O3—C11—O2122.8 (3)
O1—C6—C7113.2 (3)O3—C11—C3122.3 (3)
C8—C6—C7109.2 (3)O2—C11—C3114.8 (3)
O1—C6—C5105.0 (3)C2—O1—C6123.0 (3)
C8—C6—C5110.9 (3)C11—O2—H2107 (4)
C7—C6—C5114.7 (3)
O1—C2—C3—C11170.3 (3)Br1—C5—C6—C871.4 (4)
C10—C2—C3—C1177.5 (4)C4—C5—C6—C769.8 (4)
C9—C2—C3—C1145.5 (4)Br1—C5—C6—C752.8 (4)
O1—C2—C3—C446.7 (4)C4—C3—C11—O315.6 (5)
C10—C2—C3—C4158.8 (3)C2—C3—C11—O3109.4 (4)
C9—C2—C3—C478.1 (4)C4—C3—C11—O2163.7 (4)
C11—C3—C4—C5178.0 (3)C2—C3—C11—O271.4 (5)
C2—C3—C4—C553.0 (4)C10—C2—O1—C6169.9 (3)
C3—C4—C5—C658.8 (4)C9—C2—O1—C672.8 (4)
C3—C4—C5—Br1176.6 (3)C3—C2—O1—C651.8 (4)
C4—C5—C6—O155.1 (4)C8—C6—O1—C2171.2 (3)
Br1—C5—C6—O1177.7 (2)C7—C6—O1—C270.9 (4)
C4—C5—C6—C8166.0 (3)C5—C6—O1—C255.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O3i0.81 (1)1.83 (1)2.645 (4)176 (6)
Symmetry code: (i) x, y+1, z+1.
 

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