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The heterocyclic ring in the title compound, C13H17BrO, adopts a 1C4 conformation, with the phenyl and bromo substituents located in equatorial positions.
Supporting information
CCDC reference: 262426
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.007 Å
- R factor = 0.031
- wR factor = 0.073
- Data-to-parameter ratio = 10.9
checkCIF/PLATON results
No syntax errors found
Alert level A
THETM01_ALERT_3_A The value of sine(theta_max)/wavelength is less than 0.550
Calculated sin(theta_max)/wavelength = 0.5380
| Author Response: I wish to point out that the theta range used for the analysis of
(I) is lower than meanwhile required by the Union of Crystallography.
The compound was prepared in a project that ended several years ago.
The meassurement was performed using the theta range that was state
of the art at that time.
The compound in questions is hard to purify and to crystallize,
since it is prone to thermal and photochemical decomposition. Therefore,
it is no longer available in our laboratory. In
view of the fact that the structure is an organic compound, which scatters
with little intensity at high theta values we feel that the presented
structural information on this compound is reliable enough in order to merit
publication in Acta Crystallograhica E.
|
PLAT023_ALERT_3_A Resolution (too) Low [sin(th)/Lambda < 0.6]..... 22.48 Deg.
| Author Response: Please refer to the arguments given above at vrf_THETM01_I
|
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 22.48 Deg.
| Author Response: Please refer to the arguments given above at vrf_THETM01_PS57
|
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 2
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
Alert level G
ABSTY01_ALERT_1_G Extra text has been found in the _exptl_absorpt_correction_type
field, which should be only a single keyword. A literature
citation should be included in the _exptl_absorpt_process_details
field.
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 22.48
From the CIF: _reflns_number_total 1598
Count of symmetry unique reflns 970
Completeness (_total/calc) 164.74%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 628
Fraction of Friedel pairs measured 0.647
Are heavy atom types Z>Si present yes
3 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
1 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
4 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
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: PLATON (Spek, 2002) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
cis-(3
R,5
R)-3-Bromo-2,2-dimethyl-5-phenyltetrahydropyran
top
Crystal data top
C13H17BrO | Dx = 1.462 Mg m−3 |
Mr = 269.18 | Melting point: 337 K |
Orthorhombic, P21212 | Mo Kα radiation, λ = 0.71073 Å |
a = 13.269 (2) Å | Cell parameters from 25 reflections |
b = 16.085 (2) Å | θ = 10–15° |
c = 5.7278 (4) Å | µ = 3.34 mm−1 |
V = 1222.5 (3) Å3 | T = 173 K |
Z = 4 | Block, colourless |
F(000) = 552 | 0.30 × 0.20 × 0.20 mm |
Data collection top
Enraf–Nonius CAD-4 diffractometer | 1360 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.036 |
Graphite monochromator | θmax = 22.5°, θmin = 3.1° |
ω/2θ scans | h = −14→8 |
Absorption correction: empirical from ψ scan (North et al., 1968) | k = 0→17 |
Tmin = 0.402, Tmax = 0.513 | l = −6→6 |
2915 measured reflections | 3 standard reflections every 100 reflections |
1598 independent reflections | intensity decay: none |
Refinement top
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)] = 0.031 | H-atom parameters constrained |
wR(F2) = 0.073 | w = 1/[σ2(Fo2) + (0.0348P)2 + 0.2533P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
1598 reflections | Δρmax = 0.39 e Å−3 |
146 parameters | Δρmin = −0.27 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 628 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.009 (19) |
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 | x | y | z | Uiso*/Ueq | |
C2 | 0.0188 (3) | 0.1919 (3) | 0.1890 (8) | 0.0314 (12) | |
C3 | 0.0766 (3) | 0.2727 (3) | 0.2293 (9) | 0.0365 (13) | |
H3 | 0.118 (3) | 0.281 (2) | 0.080 (8) | 0.030 (12)* | |
C4 | 0.0119 (4) | 0.3481 (3) | 0.2745 (8) | 0.0304 (12) | |
H4A | 0.0548 | 0.3980 | 0.2937 | 0.037* | |
H4B | −0.0277 | 0.3402 | 0.4193 | 0.037* | |
C5 | −0.0595 (4) | 0.3594 (3) | 0.0641 (9) | 0.0360 (14) | |
H5 | −0.014 (3) | 0.374 (2) | −0.081 (8) | 0.026 (12)* | |
C6 | −0.1159 (3) | 0.2776 (2) | 0.0271 (11) | 0.0384 (12) | |
H6A | −0.1582 | 0.2657 | 0.1656 | 0.046* | |
H6B | −0.1611 | 0.2829 | −0.1098 | 0.046* | |
C7 | −0.0418 (4) | 0.1617 (3) | 0.3955 (10) | 0.0478 (14) | |
H7A | −0.0760 | 0.2090 | 0.4691 | 0.072* | |
H7B | 0.0033 | 0.1353 | 0.5090 | 0.072* | |
H7C | −0.0921 | 0.1213 | 0.3425 | 0.072* | |
C8 | 0.0859 (4) | 0.1246 (3) | 0.0938 (10) | 0.0488 (15) | |
H8A | 0.0453 | 0.0753 | 0.0579 | 0.073* | |
H8B | 0.1371 | 0.1102 | 0.2102 | 0.073* | |
H8C | 0.1189 | 0.1443 | −0.0489 | 0.073* | |
C9 | −0.1333 (4) | 0.4298 (3) | 0.0936 (9) | 0.0348 (13) | |
C10 | −0.1450 (4) | 0.4883 (4) | −0.0862 (9) | 0.0421 (14) | |
H10 | −0.1042 | 0.4849 | −0.2221 | 0.051* | |
C11 | −0.2169 (5) | 0.5520 (3) | −0.0657 (10) | 0.0484 (16) | |
H11 | −0.2250 | 0.5913 | −0.1881 | 0.058* | |
C12 | −0.2758 (5) | 0.5575 (4) | 0.1322 (12) | 0.0500 (16) | |
H12 | −0.3248 | 0.6003 | 0.1463 | 0.060* | |
C13 | −0.2633 (4) | 0.5009 (3) | 0.3079 (10) | 0.0465 (14) | |
H13 | −0.3037 | 0.5048 | 0.4444 | 0.056* | |
C14 | −0.1935 (4) | 0.4391 (3) | 0.2894 (9) | 0.0391 (13) | |
H14 | −0.1858 | 0.4011 | 0.4152 | 0.047* | |
O1 | −0.0479 (2) | 0.21043 (16) | −0.0097 (7) | 0.0392 (8) | |
Br1 | 0.17155 (3) | 0.25918 (2) | 0.49307 (11) | 0.04250 (18) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C2 | 0.026 (3) | 0.031 (2) | 0.038 (3) | 0.001 (2) | −0.006 (2) | 0.000 (2) |
C3 | 0.028 (3) | 0.049 (3) | 0.032 (3) | 0.000 (3) | −0.003 (2) | 0.001 (3) |
C4 | 0.034 (3) | 0.026 (2) | 0.032 (3) | −0.004 (2) | −0.006 (2) | −0.002 (2) |
C5 | 0.037 (3) | 0.039 (3) | 0.031 (4) | −0.002 (2) | −0.002 (2) | 0.001 (2) |
C6 | 0.034 (2) | 0.039 (2) | 0.043 (3) | 0.003 (2) | −0.013 (3) | −0.011 (3) |
C7 | 0.049 (4) | 0.051 (3) | 0.043 (3) | −0.008 (3) | 0.007 (3) | 0.000 (3) |
C8 | 0.045 (4) | 0.050 (3) | 0.052 (4) | 0.001 (3) | 0.004 (3) | −0.006 (3) |
C9 | 0.032 (3) | 0.031 (3) | 0.041 (3) | −0.002 (2) | −0.013 (2) | −0.003 (2) |
C10 | 0.035 (3) | 0.053 (3) | 0.038 (3) | −0.016 (3) | −0.007 (2) | −0.001 (3) |
C11 | 0.055 (4) | 0.036 (3) | 0.054 (4) | −0.007 (3) | −0.031 (3) | 0.013 (3) |
C12 | 0.044 (4) | 0.039 (3) | 0.066 (4) | 0.004 (3) | −0.018 (3) | −0.009 (3) |
C13 | 0.043 (4) | 0.045 (3) | 0.052 (4) | 0.005 (3) | −0.003 (3) | −0.008 (3) |
C14 | 0.040 (3) | 0.038 (3) | 0.039 (3) | −0.001 (3) | −0.004 (3) | −0.003 (2) |
O1 | 0.0404 (17) | 0.0384 (15) | 0.0388 (19) | 0.0024 (14) | 0.000 (2) | −0.009 (2) |
Br1 | 0.0336 (3) | 0.0498 (3) | 0.0440 (3) | 0.0010 (2) | −0.0124 (3) | 0.0018 (4) |
Geometric parameters (Å, º) top
C2—O1 | 1.472 (6) | C7—H7B | 0.9800 |
C2—C8 | 1.504 (6) | C7—H7C | 0.9800 |
C2—C7 | 1.511 (7) | C8—H8A | 0.9800 |
C2—C3 | 1.527 (7) | C8—H8B | 0.9800 |
C3—C4 | 1.508 (7) | C8—H8C | 0.9800 |
C3—Br1 | 1.979 (5) | C9—C14 | 1.385 (7) |
C3—H3 | 1.03 (4) | C9—C10 | 1.404 (7) |
C4—C5 | 1.544 (6) | C10—C11 | 1.404 (8) |
C4—H4A | 0.9900 | C10—H10 | 0.9500 |
C4—H4B | 0.9900 | C11—C12 | 1.380 (8) |
C5—C9 | 1.505 (7) | C11—H11 | 0.9500 |
C5—C6 | 1.529 (7) | C12—C13 | 1.367 (8) |
C5—H5 | 1.06 (4) | C12—H12 | 0.9500 |
C6—O1 | 1.424 (5) | C13—C14 | 1.364 (7) |
C6—H6A | 0.9900 | C13—H13 | 0.9500 |
C6—H6B | 0.9900 | C14—H14 | 0.9500 |
C7—H7A | 0.9800 | | |
| | | |
O1—C2—C8 | 102.8 (4) | C2—C7—H7B | 109.5 |
O1—C2—C7 | 110.5 (4) | H7A—C7—H7B | 109.5 |
C8—C2—C7 | 111.5 (4) | C2—C7—H7C | 109.5 |
O1—C2—C3 | 104.3 (3) | H7A—C7—H7C | 109.5 |
C8—C2—C3 | 111.8 (4) | H7B—C7—H7C | 109.5 |
C7—C2—C3 | 115.0 (4) | C2—C8—H8A | 109.5 |
C4—C3—C2 | 115.1 (4) | C2—C8—H8B | 109.5 |
C4—C3—Br1 | 108.7 (3) | H8A—C8—H8B | 109.5 |
C2—C3—Br1 | 110.0 (3) | C2—C8—H8C | 109.5 |
C4—C3—H3 | 111 (2) | H8A—C8—H8C | 109.5 |
C2—C3—H3 | 105 (2) | H8B—C8—H8C | 109.5 |
Br1—C3—H3 | 108 (2) | C14—C9—C10 | 117.2 (5) |
C3—C4—C5 | 108.1 (4) | C14—C9—C5 | 123.2 (5) |
C3—C4—H4A | 110.1 | C10—C9—C5 | 119.6 (5) |
C5—C4—H4A | 110.1 | C11—C10—C9 | 120.2 (5) |
C3—C4—H4B | 110.1 | C11—C10—H10 | 119.9 |
C5—C4—H4B | 110.1 | C9—C10—H10 | 119.9 |
H4A—C4—H4B | 108.4 | C12—C11—C10 | 120.0 (5) |
C9—C5—C6 | 110.1 (4) | C12—C11—H11 | 120.0 |
C9—C5—C4 | 113.6 (4) | C10—C11—H11 | 120.0 |
C6—C5—C4 | 107.9 (4) | C13—C12—C11 | 119.5 (5) |
C9—C5—H5 | 107 (2) | C13—C12—H12 | 120.2 |
C6—C5—H5 | 111 (2) | C11—C12—H12 | 120.2 |
C4—C5—H5 | 107 (2) | C14—C13—C12 | 120.7 (6) |
O1—C6—C5 | 111.3 (4) | C14—C13—H13 | 119.6 |
O1—C6—H6A | 109.4 | C12—C13—H13 | 119.6 |
C5—C6—H6A | 109.4 | C13—C14—C9 | 122.3 (5) |
O1—C6—H6B | 109.4 | C13—C14—H14 | 118.9 |
C5—C6—H6B | 109.4 | C9—C14—H14 | 118.9 |
H6A—C6—H6B | 108.0 | C6—O1—C2 | 114.9 (4) |
C2—C7—H7A | 109.5 | | |
| | | |
O1—C2—C3—C4 | 57.1 (5) | C6—C5—C9—C10 | −107.9 (5) |
C8—C2—C3—C4 | 167.4 (4) | C4—C5—C9—C10 | 130.9 (5) |
C7—C2—C3—C4 | −64.1 (6) | C14—C9—C10—C11 | −1.3 (7) |
O1—C2—C3—Br1 | −179.8 (3) | C5—C9—C10—C11 | 177.0 (5) |
C8—C2—C3—Br1 | −69.5 (5) | C9—C10—C11—C12 | 0.4 (7) |
C7—C2—C3—Br1 | 59.0 (5) | C10—C11—C12—C13 | 0.3 (8) |
C2—C3—C4—C5 | −57.9 (5) | C11—C12—C13—C14 | −0.2 (8) |
Br1—C3—C4—C5 | 178.3 (3) | C12—C13—C14—C9 | −0.8 (8) |
C3—C4—C5—C9 | 176.4 (4) | C10—C9—C14—C13 | 1.5 (7) |
C3—C4—C5—C6 | 54.0 (5) | C5—C9—C14—C13 | −176.7 (5) |
C9—C5—C6—O1 | 177.9 (5) | C5—C6—O1—C2 | 63.3 (5) |
C4—C5—C6—O1 | −57.6 (6) | C8—C2—O1—C6 | −175.7 (4) |
C6—C5—C9—C14 | 70.3 (6) | C7—C2—O1—C6 | 65.2 (5) |
C4—C5—C9—C14 | −50.8 (6) | C3—C2—O1—C6 | −59.0 (5) |
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