(5-Bromo-2-hy-droxy-phen-yl)(4-propyl-cyclo-hex-yl)methanone.

In the title compound, C(16)H(21)BrO(2), the cyclo-hexane ring adopts a chair conformation. The hy-droxy and carbonyl groups are involved in an intra-molecular O-H⋯O hydrogen bond. In the crystal, weak C-H⋯O inter-actions link the mol-ecules into zigzag chains along [010].

Related literature

For details of the biological activity of SGLT2 inhibitors, see: Meng et al. (2008 ▶); Gao et al. (2010 ▶); Shao et al. (2011 ▶). For related structures, see: Robinson et al. (2002 ▶); Wang et al. (2011 ▶).

Experimental

Crystal data

C16H21BrO2

M = 325.24

Monoclinic,

a = 14.5826 (12) Å

b = 8.5467 (8) Å

c = 12.6369 (10) Å

β = 113.037 (5)°

V = 1449.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 2.83 mm−1

T = 113 K

0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn 724 CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku/MSC, 2009 ▶) T min = 0.601, T max = 0.727

17988 measured reflections

3441 independent reflections

3069 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.062

S = 1.04

3441 reflections

177 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.81 e Å−3

Δρmin = −0.34 e Å−3

Data collection: CrystalClear-SM Expert (Rigaku/MSC, 2009 ▶); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; 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 datablock(s) I, global. DOI: 10.1107/S1600536812011634/cv5261sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011634/cv5261Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812011634/cv5261Isup3.cml

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

C16H21BrO2	F(000) = 672
Mr = 325.24	Dx = 1.490 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5072 reflections
a = 14.5826 (12) Å	θ = 1.8–27.9°
b = 8.5467 (8) Å	µ = 2.83 mm−1
c = 12.6369 (10) Å	T = 113 K
β = 113.037 (5)°	Prism, colourless
V = 1449.4 (2) Å3	0.20 × 0.18 × 0.12 mm
Z = 4

Rigaku Saturn 724 CCD area-detector diffractometer	3441 independent reflections
Radiation source: rotating anode	3069 reflections with I > 2σ(I)
Multilayer monochromator	Rint = 0.035
Detector resolution: 14.22 pixels mm-1	θmax = 27.9°, θmin = 2.8°
ω and φ scans	h = −19→19
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku/MSC, 2009)	k = −11→11
Tmin = 0.601, Tmax = 0.727	l = −16→16
17988 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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.062	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0334P)2 + 0.0947P] where P = (Fo2 + 2Fc2)/3
3441 reflections	(Δ/σ)max = 0.002
177 parameters	Δρmax = 0.81 e Å−3
0 restraints	Δρmin = −0.34 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	1.101943 (12)	0.65152 (2)	0.057741 (15)	0.02149 (7)
O1	0.80421 (9)	1.03963 (14)	−0.31892 (10)	0.0200 (3)
H1	0.759 (2)	1.066 (3)	−0.301 (2)	0.058 (8)*
O2	0.69906 (9)	1.05226 (14)	−0.19829 (10)	0.0202 (3)
C1	0.92537 (13)	0.83440 (18)	−0.04336 (14)	0.0169 (3)
H1A	0.9181	0.8160	0.0271	0.020*
C2	1.00541 (12)	0.77214 (19)	−0.06037 (14)	0.0174 (3)
C3	1.01921 (13)	0.8002 (2)	−0.16215 (15)	0.0197 (4)
H3	1.0747	0.7565	−0.1733	0.024*
C4	0.95127 (13)	0.8920 (2)	−0.24620 (15)	0.0193 (4)
H4	0.9610	0.9135	−0.3148	0.023*
C5	0.86871 (13)	0.95348 (19)	−0.23174 (14)	0.0170 (3)
C6	0.85425 (12)	0.92496 (19)	−0.12913 (14)	0.0153 (3)
C7	0.76554 (12)	0.99105 (19)	−0.11519 (14)	0.0157 (3)
C8	0.75600 (12)	0.98403 (19)	−0.00005 (13)	0.0153 (3)
H8	0.8240	0.9946	0.0623	0.018*
C9	0.69103 (13)	1.11868 (19)	0.01104 (14)	0.0174 (4)
H9A	0.7221	1.2196	0.0053	0.021*
H9B	0.6247	1.1133	−0.0530	0.021*
C10	0.67844 (13)	1.11146 (19)	0.12561 (14)	0.0169 (4)
H10A	0.7440	1.1282	0.1893	0.020*
H10B	0.6335	1.1968	0.1283	0.020*
C11	0.63570 (12)	0.95477 (18)	0.14288 (13)	0.0154 (3)
H11	0.5675	0.9435	0.0812	0.018*
C12	0.70000 (13)	0.82152 (19)	0.12971 (14)	0.0174 (4)
H12A	0.6697	0.7205	0.1368	0.021*
H12B	0.7668	0.8276	0.1928	0.021*
C13	0.71144 (13)	0.82583 (19)	0.01480 (14)	0.0164 (3)
H13A	0.6456	0.8109	−0.0487	0.020*
H13B	0.7556	0.7396	0.0116	0.020*
C14	0.62659 (13)	0.9434 (2)	0.25955 (14)	0.0183 (4)
H14A	0.5998	0.8389	0.2656	0.022*
H14B	0.6942	0.9509	0.3211	0.022*
C15	0.56089 (13)	1.0669 (2)	0.28140 (15)	0.0202 (4)
H15A	0.4955	1.0692	0.2156	0.024*
H15B	0.5923	1.1709	0.2869	0.024*
C16	0.54478 (14)	1.0347 (2)	0.39195 (15)	0.0247 (4)
H16A	0.5087	0.9359	0.3843	0.037*
H16B	0.5059	1.1201	0.4056	0.037*
H16C	0.6095	1.0276	0.4568	0.037*

	U11	U22	U33	U12	U13	U23
Br1	0.01672 (10)	0.02144 (10)	0.02637 (11)	0.00224 (7)	0.00849 (8)	0.00249 (7)
O1	0.0228 (7)	0.0202 (6)	0.0201 (6)	0.0024 (5)	0.0115 (6)	0.0036 (5)
O2	0.0184 (6)	0.0240 (6)	0.0187 (6)	0.0029 (5)	0.0077 (5)	0.0018 (5)
C1	0.0178 (8)	0.0165 (8)	0.0184 (8)	−0.0028 (7)	0.0094 (7)	−0.0016 (7)
C2	0.0158 (8)	0.0140 (8)	0.0215 (9)	−0.0014 (7)	0.0063 (7)	−0.0009 (7)
C3	0.0195 (9)	0.0169 (8)	0.0267 (9)	−0.0027 (7)	0.0135 (8)	−0.0054 (7)
C4	0.0225 (9)	0.0189 (8)	0.0213 (9)	−0.0041 (7)	0.0139 (8)	−0.0025 (7)
C5	0.0202 (9)	0.0138 (8)	0.0176 (8)	−0.0040 (7)	0.0079 (7)	−0.0033 (7)
C6	0.0168 (8)	0.0129 (8)	0.0173 (8)	−0.0028 (7)	0.0080 (7)	−0.0023 (6)
C7	0.0163 (8)	0.0130 (8)	0.0185 (8)	−0.0029 (6)	0.0075 (7)	−0.0016 (7)
C8	0.0142 (8)	0.0163 (8)	0.0162 (8)	−0.0005 (7)	0.0069 (7)	−0.0006 (6)
C9	0.0200 (9)	0.0151 (8)	0.0201 (9)	0.0005 (7)	0.0112 (7)	0.0011 (7)
C10	0.0195 (9)	0.0148 (8)	0.0199 (9)	0.0009 (7)	0.0115 (7)	−0.0007 (7)
C11	0.0155 (8)	0.0158 (8)	0.0150 (8)	0.0009 (6)	0.0061 (7)	0.0003 (7)
C12	0.0192 (9)	0.0152 (8)	0.0198 (9)	0.0020 (7)	0.0098 (7)	0.0039 (7)
C13	0.0179 (8)	0.0146 (8)	0.0185 (8)	0.0006 (6)	0.0089 (7)	−0.0017 (7)
C14	0.0194 (9)	0.0187 (8)	0.0181 (8)	−0.0002 (7)	0.0089 (7)	0.0014 (7)
C15	0.0205 (9)	0.0218 (9)	0.0202 (9)	0.0020 (7)	0.0100 (7)	0.0006 (7)
C16	0.0285 (10)	0.0260 (10)	0.0245 (9)	−0.0005 (8)	0.0157 (8)	−0.0008 (8)

Br1—C2	1.9046 (17)	C10—C11	1.528 (2)
O1—C5	1.353 (2)	C10—H10A	0.9900
O1—H1	0.81 (2)	C10—H10B	0.9900
O2—C7	1.233 (2)	C11—C12	1.525 (2)
C1—C2	1.374 (2)	C11—C14	1.534 (2)
C1—C6	1.403 (2)	C11—H11	1.0000
C1—H1A	0.9500	C12—C13	1.525 (2)
C2—C3	1.398 (2)	C12—H12A	0.9900
C3—C4	1.379 (2)	C12—H12B	0.9900
C3—H3	0.9500	C13—H13A	0.9900
C4—C5	1.390 (2)	C13—H13B	0.9900
C4—H4	0.9500	C14—C15	1.522 (2)
C5—C6	1.414 (2)	C14—H14A	0.9900
C6—C7	1.484 (2)	C14—H14B	0.9900
C7—C8	1.516 (2)	C15—C16	1.530 (2)
C8—C9	1.531 (2)	C15—H15A	0.9900
C8—C13	1.543 (2)	C15—H15B	0.9900
C8—H8	1.0000	C16—H16A	0.9800
C9—C10	1.530 (2)	C16—H16B	0.9800
C9—H9A	0.9900	C16—H16C	0.9800
C9—H9B	0.9900
C5—O1—H1	107.5 (19)	C9—C10—H10B	109.2
C2—C1—C6	120.60 (15)	H10A—C10—H10B	107.9
C2—C1—H1A	119.7	C12—C11—C10	109.65 (13)
C6—C1—H1A	119.7	C12—C11—C14	110.22 (13)
C1—C2—C3	120.96 (16)	C10—C11—C14	112.72 (13)
C1—C2—Br1	119.98 (13)	C12—C11—H11	108.0
C3—C2—Br1	119.03 (13)	C10—C11—H11	108.0
C4—C3—C2	119.17 (16)	C14—C11—H11	108.0
C4—C3—H3	120.4	C11—C12—C13	112.75 (13)
C2—C3—H3	120.4	C11—C12—H12A	109.0
C3—C4—C5	120.81 (16)	C13—C12—H12A	109.0
C3—C4—H4	119.6	C11—C12—H12B	109.0
C5—C4—H4	119.6	C13—C12—H12B	109.0
O1—C5—C4	117.44 (15)	H12A—C12—H12B	107.8
O1—C5—C6	122.35 (15)	C12—C13—C8	110.19 (13)
C4—C5—C6	120.21 (16)	C12—C13—H13A	109.6
C1—C6—C5	118.23 (15)	C8—C13—H13A	109.6
C1—C6—C7	122.23 (15)	C12—C13—H13B	109.6
C5—C6—C7	119.54 (15)	C8—C13—H13B	109.6
O2—C7—C6	119.47 (14)	H13A—C13—H13B	108.1
O2—C7—C8	119.83 (14)	C15—C14—C11	115.33 (14)
C6—C7—C8	120.70 (14)	C15—C14—H14A	108.4
C7—C8—C9	110.51 (13)	C11—C14—H14A	108.4
C7—C8—C13	110.65 (13)	C15—C14—H14B	108.4
C9—C8—C13	110.01 (13)	C11—C14—H14B	108.4
C7—C8—H8	108.5	H14A—C14—H14B	107.5
C9—C8—H8	108.5	C14—C15—C16	111.95 (14)
C13—C8—H8	108.5	C14—C15—H15A	109.2
C10—C9—C8	111.34 (13)	C16—C15—H15A	109.2
C10—C9—H9A	109.4	C14—C15—H15B	109.2
C8—C9—H9A	109.4	C16—C15—H15B	109.2
C10—C9—H9B	109.4	H15A—C15—H15B	107.9
C8—C9—H9B	109.4	C15—C16—H16A	109.5
H9A—C9—H9B	108.0	C15—C16—H16B	109.5
C11—C10—C9	112.15 (13)	H16A—C16—H16B	109.5
C11—C10—H10A	109.2	C15—C16—H16C	109.5
C9—C10—H10A	109.2	H16A—C16—H16C	109.5
C11—C10—H10B	109.2	H16B—C16—H16C	109.5
C6—C1—C2—C3	1.4 (3)	O2—C7—C8—C9	−27.0 (2)
C6—C1—C2—Br1	179.29 (12)	C6—C7—C8—C9	152.95 (14)
C1—C2—C3—C4	0.1 (3)	O2—C7—C8—C13	95.07 (18)
Br1—C2—C3—C4	−177.77 (13)	C6—C7—C8—C13	−84.95 (18)
C2—C3—C4—C5	−1.4 (3)	C7—C8—C9—C10	178.66 (13)
C3—C4—C5—O1	−178.60 (15)	C13—C8—C9—C10	56.18 (18)
C3—C4—C5—C6	1.2 (3)	C8—C9—C10—C11	−56.10 (18)
C2—C1—C6—C5	−1.6 (2)	C9—C10—C11—C12	54.50 (18)
C2—C1—C6—C7	178.51 (15)	C9—C10—C11—C14	177.69 (14)
O1—C5—C6—C1	−179.88 (15)	C10—C11—C12—C13	−55.68 (18)
C4—C5—C6—C1	0.3 (2)	C14—C11—C12—C13	179.67 (14)
O1—C5—C6—C7	0.0 (2)	C11—C12—C13—C8	57.25 (18)
C4—C5—C6—C7	−179.81 (15)	C7—C8—C13—C12	−178.73 (13)
C1—C6—C7—O2	−170.67 (15)	C9—C8—C13—C12	−56.33 (17)
C5—C6—C7—O2	9.5 (2)	C12—C11—C14—C15	−177.88 (14)
C1—C6—C7—C8	9.3 (2)	C10—C11—C14—C15	59.25 (19)
C5—C6—C7—C8	−170.52 (15)	C11—C14—C15—C16	172.51 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.81 (2)	1.82 (2)	2.5527 (16)	148 (3)
C3—H3···O1i	0.95	2.59	3.483 (2)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.81 (2)	1.82 (2)	2.5527 (16)	148 (3)
C3—H3⋯O1i	0.95	2.59	3.483 (2)	157

Symmetry code: (i) .