(5-Bromo-2-meth-oxy-phen-yl)(4-ethyl-cyclo-hex-yl)methanone.

In the title compound, C(16)H(21)BrO(2), the cyclo-hexane ring is in a chair conformation and its least-squares plane is at an angle of 61.3 (9)° to the benzene ring. The crystal packing is stabilized by weak π-π stacking inter-actions [centroid-centroid distance = 3.697 (9) Å] between the bromo-meth-oxy-phenyl rings of neighbouring mol-ecules.

Related literature

For the anti­hyperglycemic activity of SGLT2 inhibitors, see: Gao et al. (2010 ▶); Meng et al. (2008 ▶); Shao et al. (2010 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H21BrO2

M = 325.24

Monoclinic,

a = 14.204 (3) Å

b = 11.276 (2) Å

c = 9.604 (2) Å

β = 102.329 (4)°

V = 1502.8 (6) Å3

Z = 4

Mo Kα radiation

μ = 2.73 mm−1

T = 113 K

0.26 × 0.22 × 0.20 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ▶) T min = 0.537, T max = 0.611

13836 measured reflections

3588 independent reflections

2581 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.058

S = 1.04

3588 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrystalClear (Rigaku, 2007 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811013687/bx2347sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013687/bx2347Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H21BrO2	F(000) = 672
Mr = 325.24	Dx = 1.438 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5413 reflections
a = 14.204 (3) Å	θ = 2.2–27.9°
b = 11.276 (2) Å	µ = 2.73 mm−1
c = 9.604 (2) Å	T = 113 K
β = 102.329 (4)°	Prism, colorless
V = 1502.8 (6) Å3	0.26 × 0.22 × 0.20 mm
Z = 4

Rigaku Saturn CCD area-detector diffractometer	3588 independent reflections
Radiation source: rotating anode	2581 reflections with I > 2σ(I)
multilayer	Rint = 0.033
Detector resolution: 14.63 pixels mm-1	θmax = 27.9°, θmin = 2.3°
ω and φ scans	h = −18→18
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	k = −14→11
Tmin = 0.537, Tmax = 0.611	l = −12→12
13836 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.058	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.026P)2] where P = (Fo2 + 2Fc2)/3
3588 reflections	(Δ/σ)max = 0.001
174 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

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.

	x	y	z	Uiso*/Ueq
Br1	0.359389 (12)	1.039199 (15)	0.078211 (19)	0.02887 (7)
O1	0.67370 (8)	1.14977 (9)	0.58965 (11)	0.0236 (3)
O2	0.71492 (8)	0.90082 (11)	0.30034 (13)	0.0339 (3)
C1	0.66083 (12)	1.24071 (14)	0.68801 (17)	0.0272 (4)
H1A	0.6506	1.3170	0.6382	0.041*
H1B	0.7184	1.2455	0.7650	0.041*
H1C	0.6047	1.2219	0.7281	0.041*
C2	0.59954 (11)	1.12527 (13)	0.47931 (16)	0.0176 (3)
C3	0.51379 (11)	1.19027 (13)	0.45009 (17)	0.0202 (4)
H3	0.5046	1.2526	0.5124	0.024*
C4	0.44236 (11)	1.16512 (13)	0.33205 (17)	0.0212 (4)
H4	0.3845	1.2102	0.3123	0.025*
C5	0.45613 (11)	1.07334 (14)	0.24293 (17)	0.0193 (4)
C6	0.54008 (11)	1.00793 (14)	0.26967 (17)	0.0181 (3)
H6	0.5482	0.9459	0.2063	0.022*
C7	0.61305 (11)	1.03146 (12)	0.38797 (16)	0.0160 (3)
C8	0.70157 (11)	0.95429 (13)	0.40477 (17)	0.0192 (3)
C9	0.77081 (11)	0.93956 (12)	0.54697 (17)	0.0170 (3)
H9	0.7377	0.9641	0.6244	0.020*
C10	0.80398 (11)	0.81086 (13)	0.57217 (17)	0.0205 (4)
H10A	0.7474	0.7589	0.5690	0.025*
H10B	0.8367	0.7853	0.4960	0.025*
C11	0.87275 (11)	0.79932 (13)	0.71633 (17)	0.0208 (4)
H11A	0.8930	0.7155	0.7317	0.025*
H11B	0.8386	0.8217	0.7921	0.025*
C12	0.96177 (11)	0.87687 (13)	0.72848 (17)	0.0205 (4)
H12	0.9971	0.8502	0.6545	0.025*
C13	0.93087 (11)	1.00610 (14)	0.69645 (18)	0.0232 (4)
H13A	0.9005	1.0362	0.7731	0.028*
H13B	0.9887	1.0550	0.6959	0.028*
C14	0.86004 (10)	1.01921 (14)	0.55324 (17)	0.0205 (4)
H14A	0.8924	0.9971	0.4753	0.025*
H14B	0.8394	1.1030	0.5393	0.025*
C15	1.02894 (11)	0.86209 (15)	0.87409 (18)	0.0268 (4)
H15A	0.9958	0.8927	0.9476	0.032*
H15B	1.0405	0.7763	0.8923	0.032*
C16	1.12570 (12)	0.92389 (19)	0.8919 (2)	0.0430 (5)
H16A	1.1575	0.8988	0.8157	0.064*
H16B	1.1662	0.9029	0.9846	0.064*
H16C	1.1159	1.0099	0.8870	0.064*

	U11	U22	U33	U12	U13	U23
Br1	0.02108 (10)	0.03198 (11)	0.02822 (11)	0.00216 (7)	−0.00667 (7)	0.00102 (8)
O1	0.0236 (6)	0.0242 (6)	0.0208 (6)	0.0053 (5)	−0.0002 (5)	−0.0083 (5)
O2	0.0284 (7)	0.0513 (8)	0.0192 (7)	0.0171 (6)	−0.0011 (6)	−0.0109 (6)
C1	0.0309 (10)	0.0257 (9)	0.0242 (9)	0.0016 (8)	0.0045 (8)	−0.0107 (8)
C2	0.0187 (8)	0.0196 (8)	0.0147 (8)	−0.0011 (6)	0.0039 (7)	0.0027 (7)
C3	0.0238 (9)	0.0182 (8)	0.0206 (9)	0.0022 (7)	0.0094 (7)	0.0016 (7)
C4	0.0177 (8)	0.0209 (9)	0.0265 (9)	0.0031 (6)	0.0081 (7)	0.0066 (7)
C5	0.0168 (8)	0.0215 (8)	0.0178 (8)	−0.0019 (6)	−0.0002 (7)	0.0053 (7)
C6	0.0209 (9)	0.0173 (8)	0.0162 (8)	−0.0005 (6)	0.0040 (7)	0.0027 (6)
C7	0.0159 (7)	0.0164 (8)	0.0162 (8)	−0.0005 (6)	0.0044 (6)	0.0034 (7)
C8	0.0164 (8)	0.0219 (8)	0.0188 (8)	0.0005 (6)	0.0028 (7)	−0.0019 (7)
C9	0.0151 (8)	0.0199 (8)	0.0157 (8)	−0.0003 (6)	0.0027 (6)	−0.0017 (7)
C10	0.0175 (8)	0.0192 (8)	0.0240 (9)	−0.0001 (6)	0.0029 (7)	−0.0020 (7)
C11	0.0215 (8)	0.0162 (8)	0.0235 (9)	0.0013 (6)	0.0024 (7)	0.0014 (7)
C12	0.0169 (8)	0.0229 (9)	0.0202 (9)	0.0017 (6)	0.0007 (7)	−0.0016 (7)
C13	0.0180 (9)	0.0205 (8)	0.0283 (10)	−0.0041 (7)	−0.0011 (8)	0.0038 (7)
C14	0.0178 (8)	0.0208 (9)	0.0225 (9)	−0.0016 (6)	0.0036 (7)	0.0036 (7)
C15	0.0244 (9)	0.0262 (9)	0.0259 (10)	0.0017 (7)	−0.0035 (8)	0.0000 (8)
C16	0.0230 (10)	0.0583 (13)	0.0406 (13)	−0.0021 (9)	−0.0089 (9)	0.0032 (10)

Br1—C5	1.9002 (16)	C10—C11	1.520 (2)
O1—C2	1.3536 (17)	C10—H10A	0.9900
O1—C1	1.4322 (17)	C10—H10B	0.9900
O2—C8	1.2192 (18)	C11—C12	1.521 (2)
C1—H1A	0.9800	C11—H11A	0.9900
C1—H1B	0.9800	C11—H11B	0.9900
C1—H1C	0.9800	C12—C15	1.524 (2)
C2—C3	1.398 (2)	C12—C13	1.534 (2)
C2—C7	1.413 (2)	C12—H12	1.0000
C3—C4	1.380 (2)	C13—C14	1.528 (2)
C3—H3	0.9500	C13—H13A	0.9900
C4—C5	1.383 (2)	C13—H13B	0.9900
C4—H4	0.9500	C14—H14A	0.9900
C5—C6	1.379 (2)	C14—H14B	0.9900
C6—C7	1.390 (2)	C15—C16	1.518 (2)
C6—H6	0.9500	C15—H15A	0.9900
C7—C8	1.509 (2)	C15—H15B	0.9900
C8—C9	1.512 (2)	C16—H16A	0.9800
C9—C10	1.529 (2)	C16—H16B	0.9800
C9—C14	1.544 (2)	C16—H16C	0.9800
C9—H9	1.0000
C2—O1—C1	118.36 (12)	C9—C10—H10B	109.7
O1—C1—H1A	109.5	H10A—C10—H10B	108.2
O1—C1—H1B	109.5	C10—C11—C12	112.50 (13)
H1A—C1—H1B	109.5	C10—C11—H11A	109.1
O1—C1—H1C	109.5	C12—C11—H11A	109.1
H1A—C1—H1C	109.5	C10—C11—H11B	109.1
H1B—C1—H1C	109.5	C12—C11—H11B	109.1
O1—C2—C3	123.32 (14)	H11A—C11—H11B	107.8
O1—C2—C7	116.91 (14)	C11—C12—C15	110.78 (13)
C3—C2—C7	119.73 (15)	C11—C12—C13	109.46 (12)
C4—C3—C2	120.91 (15)	C15—C12—C13	112.58 (13)
C4—C3—H3	119.5	C11—C12—H12	108.0
C2—C3—H3	119.5	C15—C12—H12	108.0
C3—C4—C5	119.06 (15)	C13—C12—H12	108.0
C3—C4—H4	120.5	C14—C13—C12	112.18 (13)
C5—C4—H4	120.5	C14—C13—H13A	109.2
C6—C5—C4	121.06 (15)	C12—C13—H13A	109.2
C6—C5—Br1	119.32 (12)	C14—C13—H13B	109.2
C4—C5—Br1	119.61 (12)	C12—C13—H13B	109.2
C5—C6—C7	120.96 (15)	H13A—C13—H13B	107.9
C5—C6—H6	119.5	C13—C14—C9	110.86 (13)
C7—C6—H6	119.5	C13—C14—H14A	109.5
C6—C7—C2	118.28 (14)	C9—C14—H14A	109.5
C6—C7—C8	115.86 (14)	C13—C14—H14B	109.5
C2—C7—C8	125.85 (14)	C9—C14—H14B	109.5
O2—C8—C7	118.01 (14)	H14A—C14—H14B	108.1
O2—C8—C9	120.22 (14)	C16—C15—C12	115.32 (15)
C7—C8—C9	121.75 (14)	C16—C15—H15A	108.4
C8—C9—C10	111.48 (13)	C12—C15—H15A	108.4
C8—C9—C14	109.97 (13)	C16—C15—H15B	108.4
C10—C9—C14	108.86 (13)	C12—C15—H15B	108.4
C8—C9—H9	108.8	H15A—C15—H15B	107.5
C10—C9—H9	108.8	C15—C16—H16A	109.5
C14—C9—H9	108.8	C15—C16—H16B	109.5
C11—C10—C9	109.99 (12)	H16A—C16—H16B	109.5
C11—C10—H10A	109.7	C15—C16—H16C	109.5
C9—C10—H10A	109.7	H16A—C16—H16C	109.5
C11—C10—H10B	109.7	H16B—C16—H16C	109.5
C1—O1—C2—C3	5.2 (2)	C2—C7—C8—C9	22.2 (2)
C1—O1—C2—C7	−177.20 (13)	O2—C8—C9—C10	−39.5 (2)
O1—C2—C3—C4	176.77 (14)	C7—C8—C9—C10	138.54 (14)
C7—C2—C3—C4	−0.8 (2)	O2—C8—C9—C14	81.31 (18)
C2—C3—C4—C5	0.7 (2)	C7—C8—C9—C14	−100.62 (16)
C3—C4—C5—C6	−0.6 (2)	C8—C9—C10—C11	−179.57 (13)
C3—C4—C5—Br1	−178.97 (11)	C14—C9—C10—C11	58.95 (17)
C4—C5—C6—C7	0.7 (2)	C9—C10—C11—C12	−59.46 (17)
Br1—C5—C6—C7	179.06 (11)	C10—C11—C12—C15	−179.67 (13)
C5—C6—C7—C2	−0.8 (2)	C10—C11—C12—C13	55.60 (18)
C5—C6—C7—C8	−179.56 (14)	C11—C12—C13—C14	−53.76 (18)
O1—C2—C7—C6	−176.87 (13)	C15—C12—C13—C14	−177.44 (14)
C3—C2—C7—C6	0.9 (2)	C12—C13—C14—C9	56.16 (18)
O1—C2—C7—C8	1.7 (2)	C8—C9—C14—C13	179.77 (13)
C3—C2—C7—C8	179.47 (14)	C10—C9—C14—C13	−57.84 (17)
C6—C7—C8—O2	18.9 (2)	C11—C12—C15—C16	172.94 (15)
C2—C7—C8—O2	−159.73 (16)	C13—C12—C15—C16	−64.1 (2)
C6—C7—C8—C9	−159.20 (14)