(5S,6R)-6-Bromo-6-methyl-5-phenyl-3,4,5,6-tetra­hydro-2H-cyclo­penta­[b]pyran-7-one

Ieawsuwan, W.; Bolte, M.

doi:10.1107/S1600536811038232

organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2748

https://doi.org/10.1107/S1600536811038232

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(5S,6R)-6-Bromo-6-methyl-5-phenyl-3,4,5,6-tetrahydro-2H-cyclopenta[b]pyran-7-one

Winai Ieawsuwan ^a and Michael Bolte ^b ^*

^aInstitute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany, and ^bInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Str. 7, 60438 Frankfurt/Main, Germany
^*Correspondence e-mail: bolte@chemie.uni-frankfurt.de

(Received 9 September 2011; accepted 19 September 2011; online 30 September 2011)

The title compound, C₁₅H₁₅BrO₂, was synthesized by a Brønsted acid-catalysed domino electrocyclization-halogenation reaction. The five-membered ring is essentially planar (r.m.s. deviation 0.006 Å) and forms a dihedral angle of 72.7 (3)° with the attached phenyl ring. The six-membered heterocycle adopts a half-chair conformation. The crystal packing is stabilized by a C—H⋯O contact.

Related literature

For background information, see: Rueping & Ieawsuwan (2009 ); Rueping et al. (2007 ). For the synthesis of the title compound, see: Rueping & Ieawsuwan (2011 ). For a comparable compound, see: Liang et al. (2003 ).

Experimental

Crystal data

C₁₅H₁₅BrO₂
M_r = 307.18
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.2217 (11) Å
b = 11.5041 (12) Å
c = 12.9149 (17) Å
V = 1370.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 2.99 mm⁻¹
T = 173 K
0.21 × 0.12 × 0.03 mm

Data collection

STOE IPDS II two-circle-diffractometer
Absorption correction: multi-scan (MULABS; Spek, 2009 ; Blessing, 1995 ) T_min = 0.572, T_max = 0.916
11129 measured reflections
2407 independent reflections
1849 reflections with I > 2σ(I)
R_int = 0.078

Refinement

R[F² > 2σ(F²)] = 0.082
wR(F²) = 0.217
S = 1.03
2407 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 1.07 e Å⁻³
Δρ_min = −1.13 e Å⁻³
Absolute structure: Flack (1983 ), 1009 Friedel pairs
Flack parameter: 0.02 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O31ⁱ	1.00	2.47	3.282 (9)	138
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2001 ); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811038232/ds2143sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811038232/ds2143Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811038232/ds2143Isup3.cml

checkCIF report

Comment top

Trans-4,5-substituted 5-bromocyclopentenone derivatives have been prepared by a organocatalyzed cascade protocol (Rueping & Ieawsuwan, 2009; Rueping et al., 2007). The Brønsted acid catalyzed domino electrocyclization-halogenation reaction provides for the first time, a variety of α-brominated cyclopent-2-enones with a wide substrate scope and with excellent enantioselectivities (Rueping & Ieawsuwan, 2011). Two chiral centers, a tertiary and a quaternary one, can be established during this transformation. The title compound was synthesized for the first time following this reaction and yellow needles suitable for crystal structure determination were obtained.

The five membered ring in the title compound is essentially planar (r.m.s. deviation 0.006 Å) and forms a dihedral angle of 72.7 (3)° with the attached phenyl ring. The six-membered heterocycle adopts a half chair conformation.

A comparable structure, cis-6-Methyl-5-phenyl-3,4,5,6-tetrahydro-2H-cyclopenta(b)pyran-7-one, with an H atom instead of a bromine residue (Liang et al., 2003) has essentially the same conformation (r.m.s. deviation for all C and O atoms 0.183 Å) (Fig. 2).

The crystal packing is stabilized by a C—H···O contact (Table 2).

Related literature top

For background information, see: Rueping & Ieawsuwan (2009); Rueping et al. (2007). For the synthesis of the title compound, see: Rueping & Ieawsuwan (2011). For a comparable compound, see: Liang et al. (2003).

Experimental top

The title compound has been synthesized as described by Rueping & Ieawsuwan (2011).

Structure description top

The crystal packing is stabilized by a C—H···O contact (Table 2).

For background information, see: Rueping & Ieawsuwan (2009); Rueping et al. (2007). For the synthesis of the title compound, see: Rueping & Ieawsuwan (2011). For a comparable compound, see: Liang et al. (2003).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Perspective view of the title compound with the atom numbering scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. Least-squares fit of the title compound (open bonds) with cis-6-Methyl-5-phenyl-3,4,5,6-tetrahydro-2H-cyclopenta(b)pyran-7-one (full bonds).

(5S,6R)-6-Bromo-6-methyl-5-phenyl-3,4,5,6-tetrahydro-2H- cyclopenta[b]pyran-7-one top

Crystal data top

C₁₅H₁₅BrO₂	F(000) = 624
M_r = 307.18	D_x = 1.489 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7315 reflections
a = 9.2217 (11) Å	θ = 3.6–25.5°
b = 11.5041 (12) Å	µ = 2.99 mm⁻¹
c = 12.9149 (17) Å	T = 173 K
V = 1370.1 (3) Å³	Needle, colourless
Z = 4	0.21 × 0.12 × 0.03 mm

Data collection top

STOE IPDS II two-circle- diffractometer	2407 independent reflections
Radiation source: fine-focus sealed tube	1849 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.078
ω scans	θ_max = 25.0°, θ_min = 3.5°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −10→10
T_min = 0.572, T_max = 0.916	k = −13→13
11129 measured reflections	l = −15→15

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)] = 0.082	H-atom parameters constrained
wR(F²) = 0.217	w = 1/[σ²(F_o²) + (0.1273P)² + 1.2132P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2407 reflections	Δρ_max = 1.07 e Å⁻³
163 parameters	Δρ_min = −1.13 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1009 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (3)

Crystal data top

C₁₅H₁₅BrO₂	V = 1370.1 (3) Å³
M_r = 307.18	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.2217 (11) Å	µ = 2.99 mm⁻¹
b = 11.5041 (12) Å	T = 173 K
c = 12.9149 (17) Å	0.21 × 0.12 × 0.03 mm

Data collection top

STOE IPDS II two-circle- diffractometer	2407 independent reflections
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	1849 reflections with I > 2σ(I)
T_min = 0.572, T_max = 0.916	R_int = 0.078
11129 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.082	H-atom parameters constrained
wR(F²) = 0.217	Δρ_max = 1.07 e Å⁻³
S = 1.03	Δρ_min = −1.13 e Å⁻³
2407 reflections	Absolute structure: Flack (1983), 1009 Friedel pairs
163 parameters	Absolute structure parameter: 0.02 (3)
0 restraints

Special details top

Experimental. ;

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	U_iso*/U_eq
Br1	0.4532 (2)	0.30553 (14)	0.06794 (12)	0.1312 (10)
C1	0.6283 (9)	0.3284 (6)	0.2534 (5)	0.0310 (16)
H1	0.5988	0.2457	0.2422	0.037*
C2	0.5646 (11)	0.4039 (7)	0.1618 (5)	0.0404 (19)
C3	0.4546 (10)	0.4875 (6)	0.2110 (6)	0.0343 (17)
C4	0.4544 (9)	0.4612 (5)	0.3206 (5)	0.0278 (15)
C5	0.5450 (10)	0.3752 (6)	0.3462 (5)	0.0307 (17)
C6	0.5505 (10)	0.3268 (6)	0.4533 (5)	0.0369 (18)
H6A	0.6408	0.3521	0.4880	0.044*
H6B	0.5501	0.2408	0.4505	0.044*
C7	0.4190 (11)	0.3697 (7)	0.5144 (6)	0.046 (2)
H7A	0.3318	0.3257	0.4929	0.055*
H7B	0.4348	0.3557	0.5892	0.055*
C8	0.3945 (10)	0.4988 (7)	0.4959 (6)	0.040 (2)
H8A	0.3121	0.5260	0.5386	0.048*
H8B	0.4819	0.5427	0.5170	0.048*
O9	0.3636 (7)	0.5214 (5)	0.3851 (4)	0.0397 (14)
C11	0.7886 (9)	0.3324 (6)	0.2644 (5)	0.0289 (16)
C12	0.8645 (11)	0.4156 (7)	0.3217 (7)	0.040 (2)
H12	0.8109	0.4724	0.3589	0.048*
C13	1.0115 (11)	0.4188 (7)	0.3266 (7)	0.045 (2)
H13	1.0581	0.4778	0.3659	0.054*
C14	1.0948 (10)	0.3360 (8)	0.2742 (7)	0.045 (2)
H14	1.1977	0.3366	0.2781	0.054*
C15	1.0224 (12)	0.2534 (7)	0.2169 (7)	0.047 (2)
H15	1.0777	0.1984	0.1788	0.057*
C16	0.8782 (10)	0.2473 (6)	0.2126 (7)	0.0346 (18)
H16	0.8336	0.1860	0.1748	0.042*
C21	0.6732 (16)	0.4727 (19)	0.0990 (12)	0.137 (9)
H21A	0.7434	0.4194	0.0675	0.206*
H21B	0.7241	0.5274	0.1443	0.206*
H21C	0.6225	0.5157	0.0444	0.206*
O31	0.3838 (9)	0.5587 (5)	0.1641 (5)	0.0542 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.1929 (19)	0.1099 (10)	0.0906 (10)	0.1023 (12)	−0.1072 (11)	−0.0738 (9)
C1	0.035 (4)	0.035 (4)	0.022 (4)	0.005 (3)	−0.001 (3)	0.001 (3)
C2	0.044 (5)	0.060 (5)	0.018 (3)	0.011 (4)	0.003 (4)	0.004 (3)
C3	0.038 (5)	0.037 (4)	0.028 (4)	−0.006 (3)	−0.009 (4)	0.008 (3)
C4	0.026 (4)	0.033 (3)	0.024 (3)	0.002 (3)	−0.003 (3)	−0.003 (3)
C5	0.039 (5)	0.030 (3)	0.023 (3)	−0.007 (3)	0.004 (3)	0.001 (3)
C6	0.050 (5)	0.040 (4)	0.021 (3)	−0.005 (4)	−0.003 (4)	0.007 (3)
C7	0.052 (6)	0.058 (5)	0.028 (4)	−0.006 (4)	0.011 (4)	0.009 (3)
C8	0.049 (5)	0.053 (4)	0.019 (4)	0.008 (4)	0.010 (4)	0.002 (3)
O9	0.042 (3)	0.046 (3)	0.031 (3)	0.014 (3)	−0.005 (3)	0.001 (2)
C11	0.031 (4)	0.033 (4)	0.023 (3)	−0.001 (3)	0.006 (3)	0.001 (3)
C12	0.047 (6)	0.031 (4)	0.042 (5)	−0.008 (4)	0.009 (4)	−0.010 (4)
C13	0.047 (6)	0.042 (4)	0.046 (5)	−0.019 (4)	−0.001 (4)	−0.005 (4)
C14	0.027 (5)	0.071 (6)	0.038 (4)	−0.003 (4)	0.001 (3)	0.003 (4)
C15	0.051 (7)	0.048 (4)	0.043 (5)	0.004 (4)	0.003 (4)	−0.001 (4)
C16	0.034 (5)	0.034 (4)	0.036 (4)	−0.003 (3)	0.005 (4)	−0.016 (3)
C21	0.077 (10)	0.24 (2)	0.090 (10)	0.074 (12)	0.048 (8)	0.127 (13)
O31	0.088 (5)	0.038 (3)	0.036 (3)	0.023 (3)	−0.015 (3)	0.003 (2)

Geometric parameters (Å, º) top

Br1—C2	1.951 (9)	C8—O9	1.481 (9)
C1—C11	1.486 (11)	C8—H8A	0.9900
C1—C5	1.522 (10)	C8—H8B	0.9900
C1—C2	1.582 (10)	C11—C12	1.398 (11)
C1—H1	1.0000	C11—C16	1.445 (10)
C2—C21	1.512 (17)	C12—C13	1.357 (14)
C2—C3	1.535 (12)	C12—H12	0.9500
C3—O31	1.211 (10)	C13—C14	1.398 (13)
C3—C4	1.447 (11)	C13—H13	0.9500
C4—C5	1.337 (11)	C14—C15	1.377 (13)
C4—O9	1.369 (9)	C14—H14	0.9500
C5—C6	1.491 (9)	C15—C16	1.333 (13)
C6—C7	1.528 (13)	C15—H15	0.9500
C6—H6A	0.9900	C16—H16	0.9500
C6—H6B	0.9900	C21—H21A	0.9800
C7—C8	1.521 (12)	C21—H21B	0.9800
C7—H7A	0.9900	C21—H21C	0.9800
C7—H7B	0.9900

C11—C1—C5	114.6 (6)	H7A—C7—H7B	108.1
C11—C1—C2	115.1 (7)	O9—C8—C7	110.6 (7)
C5—C1—C2	102.0 (6)	O9—C8—H8A	109.5
C11—C1—H1	108.3	C7—C8—H8A	109.5
C5—C1—H1	108.3	O9—C8—H8B	109.5
C2—C1—H1	108.3	C7—C8—H8B	109.5
C21—C2—C3	109.4 (9)	H8A—C8—H8B	108.1
C21—C2—C1	116.3 (8)	C4—O9—C8	112.4 (6)
C3—C2—C1	106.2 (6)	C12—C11—C16	115.0 (8)
C21—C2—Br1	108.6 (10)	C12—C11—C1	124.7 (7)
C3—C2—Br1	105.9 (6)	C16—C11—C1	120.2 (7)
C1—C2—Br1	110.0 (5)	C13—C12—C11	122.9 (8)
O31—C3—C4	129.1 (8)	C13—C12—H12	118.5
O31—C3—C2	124.9 (7)	C11—C12—H12	118.5
C4—C3—C2	106.0 (6)	C12—C13—C14	120.5 (8)
C5—C4—O9	127.3 (7)	C12—C13—H13	119.7
C5—C4—C3	113.3 (6)	C14—C13—H13	119.7
O9—C4—C3	119.4 (6)	C15—C14—C13	117.6 (9)
C4—C5—C6	121.8 (7)	C15—C14—H14	121.2
C4—C5—C1	112.4 (6)	C13—C14—H14	121.2
C6—C5—C1	125.5 (7)	C16—C15—C14	122.9 (9)
C5—C6—C7	109.3 (7)	C16—C15—H15	118.6
C5—C6—H6A	109.8	C14—C15—H15	118.6
C7—C6—H6A	109.8	C15—C16—C11	121.0 (8)
C5—C6—H6B	109.8	C15—C16—H16	119.5
C7—C6—H6B	109.8	C11—C16—H16	119.5
H6A—C6—H6B	108.3	C2—C21—H21A	109.5
C8—C7—C6	110.6 (7)	C2—C21—H21B	109.5
C8—C7—H7A	109.5	H21A—C21—H21B	109.5
C6—C7—H7A	109.5	C2—C21—H21C	109.5
C8—C7—H7B	109.5	H21A—C21—H21C	109.5
C6—C7—H7B	109.5	H21B—C21—H21C	109.5

C11—C1—C2—C21	−1.5 (13)	C11—C1—C5—C6	−61.6 (10)
C5—C1—C2—C21	123.2 (12)	C2—C1—C5—C6	173.4 (7)
C11—C1—C2—C3	−123.5 (7)	C4—C5—C6—C7	12.9 (10)
C5—C1—C2—C3	1.2 (8)	C1—C5—C6—C7	−161.6 (8)
C11—C1—C2—Br1	122.4 (6)	C5—C6—C7—C8	−44.3 (9)
C5—C1—C2—Br1	−112.9 (6)	C6—C7—C8—O9	61.9 (10)
C21—C2—C3—O31	53.9 (13)	C5—C4—O9—C8	11.8 (11)
C1—C2—C3—O31	−179.9 (8)	C3—C4—O9—C8	−170.1 (7)
Br1—C2—C3—O31	−63.0 (9)	C7—C8—O9—C4	−44.0 (10)
C21—C2—C3—C4	−126.8 (10)	C5—C1—C11—C12	−30.5 (10)
C1—C2—C3—C4	−0.6 (9)	C2—C1—C11—C12	87.3 (9)
Br1—C2—C3—C4	116.3 (6)	C5—C1—C11—C16	150.4 (7)
O31—C3—C4—C5	178.8 (8)	C2—C1—C11—C16	−91.8 (8)
C2—C3—C4—C5	−0.4 (9)	C16—C11—C12—C13	1.7 (12)
O31—C3—C4—O9	0.4 (13)	C1—C11—C12—C13	−177.4 (8)
C2—C3—C4—O9	−178.9 (6)	C11—C12—C13—C14	−0.9 (14)
O9—C4—C5—C6	4.4 (12)	C12—C13—C14—C15	1.1 (13)
C3—C4—C5—C6	−173.9 (7)	C13—C14—C15—C16	−2.4 (14)
O9—C4—C5—C1	179.6 (7)	C14—C15—C16—C11	3.4 (14)
C3—C4—C5—C1	1.3 (9)	C12—C11—C16—C15	−2.9 (12)
C11—C1—C5—C4	123.5 (7)	C1—C11—C16—C15	176.3 (8)
C2—C1—C5—C4	−1.6 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O31ⁱ	1.00	2.47	3.282 (9)	138

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₅BrO₂
M_r	307.18
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	173
a, b, c (Å)	9.2217 (11), 11.5041 (12), 12.9149 (17)
V (Å³)	1370.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.99
Crystal size (mm)	0.21 × 0.12 × 0.03

Data collection
Diffractometer	STOE IPDS II two-circle- diffractometer
Absorption correction	Multi-scan (MULABS; Spek, 2009; Blessing, 1995)
T_min, T_max	0.572, 0.916
No. of measured, independent and observed [I > 2σ(I)] reflections	11129, 2407, 1849
R_int	0.078
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.082, 0.217, 1.03
No. of reflections	2407
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.07, −1.13
Absolute structure	Flack (1983), 1009 Friedel pairs
Absolute structure parameter	0.02 (3)

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O31ⁱ	1.00	2.47	3.282 (9)	137.6

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

References

Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
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Volume 67| Part 10| October 2011| Page o2748

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

(5S,6R)-6-Bromo-6-methyl-5-phenyl-3,4,5,6-tetra­hydro-2H-cyclo­penta­[b]pyran-7-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

(5S,6R)-6-Bromo-6-methyl-5-phenyl-3,4,5,6-tetrahydro-2H-cyclopenta[b]pyran-7-one