cis-(3R,5R)-3-Bromo-2,2-di­methyl-5-phenyl­tetra­hydro­pyran

The heterocyclic ring in the title compound, C₁₃H₁₇BrO, adopts a ₁C⁴ conformation, with the phenyl and bromo substituents located in equatorial positions.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](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

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Computing details

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-(3R,5R)-3-Bromo-2,2-dimethyl-5-phenyltetrahydropyran

Crystal data

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) Å^3	T = 173 K
Z = 4	Block, colourless
F(000) = 552	0.30 × 0.20 × 0.20 mm

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.031	H-atom parameters constrained
wR(F^2) = 0.073	w = 1/[σ^2(Fo^2) + (0.0348P)^2 + 0.2533P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)