Literature DB >> 23125653

(4-Meth-oxy-phen-yl)(4-methyl-cyclo-hex-yl)methanone.

Wei Liu1, Lida Tang.   

Abstract

The title compound, C(15)H(20)O(2), crystallizes with two independent mol-ecules of similar geometry in the asymmetric unit. The cyclo-hexyl ring adopts a chair conformation in each mol-ecule. In the crystal, mol-ecules related by translation are linked into chains along the a axis via weak C-H⋯O inter-actions.

Entities:  

Year:  2012        PMID: 23125653      PMCID: PMC3470209          DOI: 10.1107/S1600536812037373

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


Related literature

For the anti­hyperglycemic activity of SGLT2 inhibitors, see: Shao et al. (2011 ▶); Zhao et al. (2011 ▶). For related structures, see: Meng et al. (2012 ▶); Wang et al. (2011 ▶).

Experimental

Crystal data

C15H20O2 M = 232.31 Triclinic, a = 5.7003 (18) Å b = 7.279 (2) Å c = 30.76 (1) Å α = 96.700 (9)° β = 94.380 (16)° γ = 93.332 (12)° V = 1261.0 (7) Å3 Z = 4 Mo Kα radiation μ = 0.08 mm−1 T = 113 K 0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2009 ▶) T min = 0.984, T max = 0.991 12908 measured reflections 5924 independent reflections 3739 reflections with I > 2σ(I) R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.043 wR(F 2) = 0.120 S = 1.03 5924 reflections 311 parameters H-atom parameters constrained Δρmax = 0.35 e Å−3 Δρmin = −0.18 e Å−3 Data collection: CrystalClear (Rigaku/MSC, 2009 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536812037373/cv5337sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037373/cv5337Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812037373/cv5337Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C15H20O2Z = 4
Mr = 232.31F(000) = 504
Triclinic, P1Dx = 1.224 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.7003 (18) ÅCell parameters from 4144 reflections
b = 7.279 (2) Åθ = 2.0–27.9°
c = 30.76 (1) ŵ = 0.08 mm1
α = 96.700 (9)°T = 113 K
β = 94.380 (16)°Prism, colourless
γ = 93.332 (12)°0.20 × 0.18 × 0.12 mm
V = 1261.0 (7) Å3
Rigaku Saturn CCD area-detector diffractometer5924 independent reflections
Radiation source: rotating anode3739 reflections with I > 2σ(I)
Multilayer monochromatorRint = 0.038
Detector resolution: 14.63 pixels mm-1θmax = 27.9°, θmin = 2.0°
ω and φ scansh = −7→7
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2009)k = −9→9
Tmin = 0.984, Tmax = 0.991l = −39→40
12908 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0506P)2] where P = (Fo2 + 2Fc2)/3
5924 reflections(Δ/σ)max = 0.004
311 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = −0.18 e Å3
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.
xyzUiso*/Ueq
O10.19664 (16)1.11167 (12)0.33482 (3)0.0263 (2)
O20.46796 (15)0.82156 (13)0.14498 (3)0.0305 (2)
O30.77830 (16)0.33602 (12)0.17072 (3)0.0275 (2)
O40.52284 (16)0.73059 (14)0.35409 (3)0.0334 (3)
C10.4001 (2)1.19400 (18)0.36164 (4)0.0295 (3)
H1A0.52781.10960.35980.044*
H1B0.36141.21750.39220.044*
H1C0.45061.31130.35130.044*
C20.2251 (2)1.05419 (16)0.29179 (4)0.0209 (3)
C30.4298 (2)1.08989 (16)0.27130 (4)0.0218 (3)
H30.56191.15980.28700.026*
C40.4368 (2)1.02131 (16)0.22748 (4)0.0212 (3)
H40.57721.04280.21350.025*
C50.2447 (2)0.92202 (16)0.20324 (4)0.0192 (3)
C60.0383 (2)0.89343 (16)0.22415 (4)0.0205 (3)
H6−0.09710.82980.20800.025*
C70.0302 (2)0.95706 (16)0.26805 (4)0.0213 (3)
H7−0.10940.93430.28210.026*
C80.2704 (2)0.84618 (17)0.15690 (4)0.0219 (3)
C90.0566 (2)0.80827 (17)0.12401 (4)0.0220 (3)
H9−0.08750.79170.14010.026*
C100.0752 (2)0.63558 (17)0.09157 (4)0.0272 (3)
H10A0.07430.52510.10750.033*
H10B0.22670.64530.07800.033*
C11−0.1284 (2)0.61157 (18)0.05559 (4)0.0283 (3)
H11A−0.10740.50110.03460.034*
H11B−0.27870.59040.06900.034*
C12−0.1415 (2)0.78128 (18)0.03088 (4)0.0258 (3)
H120.00950.79780.01680.031*
C13−0.1635 (2)0.95325 (18)0.06335 (4)0.0267 (3)
H13A−0.31540.94160.07670.032*
H13B−0.16451.06370.04740.032*
C140.0378 (2)0.98096 (17)0.09963 (4)0.0259 (3)
H14A0.01121.08940.12080.031*
H14B0.18811.00710.08670.031*
C15−0.3433 (3)0.7554 (2)−0.00528 (4)0.0344 (3)
H15A−0.49310.73580.00770.052*
H15B−0.31950.6475−0.02630.052*
H15C−0.34700.8664−0.02050.052*
C160.5868 (3)0.3403 (2)0.13812 (4)0.0324 (3)
H16A0.44460.27880.14740.049*
H16B0.62620.27560.11010.049*
H16C0.55820.46930.13450.049*
C170.7511 (2)0.41843 (16)0.21210 (4)0.0213 (3)
C180.5547 (2)0.51267 (16)0.22355 (4)0.0215 (3)
H180.42860.52340.20210.026*
C190.5460 (2)0.59047 (16)0.26667 (4)0.0214 (3)
H190.41110.65290.27470.026*
C200.7298 (2)0.57948 (16)0.29851 (4)0.0195 (3)
C210.9266 (2)0.48535 (16)0.28615 (4)0.0214 (3)
H211.05490.47740.30730.026*
C220.9355 (2)0.40431 (16)0.24356 (4)0.0219 (3)
H221.06810.33860.23570.026*
C230.7117 (2)0.67370 (17)0.34374 (4)0.0223 (3)
C240.9260 (2)0.69855 (17)0.37672 (4)0.0216 (3)
H241.07060.71090.36050.026*
C250.9183 (2)0.87238 (17)0.40970 (4)0.0242 (3)
H25A0.91960.98330.39390.029*
H25B0.77000.86580.42440.029*
C261.1281 (2)0.89120 (17)0.44422 (4)0.0251 (3)
H26A1.11561.00270.46540.030*
H26B1.27570.90820.42970.030*
C271.1396 (2)0.72105 (18)0.46893 (4)0.0252 (3)
H270.99180.70930.48420.030*
C281.1465 (2)0.54731 (17)0.43608 (4)0.0250 (3)
H28A1.29540.55360.42160.030*
H28B1.14510.43690.45210.030*
C290.9384 (2)0.52528 (17)0.40108 (4)0.0244 (3)
H29A0.79000.50530.41510.029*
H29B0.95520.41510.37970.029*
C301.3480 (2)0.74087 (19)0.50368 (4)0.0329 (3)
H30A1.34970.62960.51880.049*
H30B1.33300.84970.52500.049*
H30C1.49510.75610.48960.049*
U11U22U33U12U13U23
O10.0278 (5)0.0285 (5)0.0217 (5)0.0011 (4)0.0032 (4)−0.0006 (4)
O20.0202 (5)0.0442 (6)0.0272 (5)0.0045 (4)0.0047 (4)0.0015 (4)
O30.0290 (5)0.0311 (5)0.0217 (5)0.0059 (4)0.0004 (4)−0.0002 (4)
O40.0217 (5)0.0480 (6)0.0301 (6)0.0073 (5)0.0046 (4)−0.0009 (5)
C10.0333 (8)0.0294 (7)0.0232 (7)0.0005 (6)−0.0047 (6)−0.0016 (6)
C20.0240 (7)0.0176 (6)0.0220 (7)0.0046 (5)0.0028 (6)0.0040 (5)
C30.0187 (7)0.0193 (6)0.0270 (7)−0.0002 (5)−0.0017 (5)0.0042 (5)
C40.0172 (7)0.0214 (6)0.0259 (7)0.0016 (5)0.0025 (5)0.0058 (5)
C50.0175 (7)0.0183 (6)0.0227 (7)0.0032 (5)0.0009 (5)0.0058 (5)
C60.0173 (7)0.0178 (6)0.0263 (7)0.0000 (5)0.0012 (5)0.0035 (5)
C70.0197 (7)0.0195 (6)0.0256 (7)0.0000 (5)0.0050 (5)0.0055 (5)
C80.0217 (7)0.0223 (6)0.0224 (7)0.0027 (5)0.0018 (6)0.0053 (5)
C90.0182 (7)0.0279 (7)0.0197 (7)0.0013 (5)0.0024 (5)0.0022 (5)
C100.0285 (8)0.0238 (6)0.0288 (8)0.0031 (6)−0.0009 (6)0.0025 (6)
C110.0295 (8)0.0265 (7)0.0269 (8)0.0009 (6)−0.0016 (6)−0.0018 (6)
C120.0243 (7)0.0334 (7)0.0189 (7)0.0012 (6)0.0026 (6)0.0001 (6)
C130.0281 (8)0.0282 (7)0.0241 (7)0.0049 (6)0.0000 (6)0.0043 (6)
C140.0267 (7)0.0245 (7)0.0253 (7)0.0021 (6)−0.0017 (6)0.0000 (6)
C150.0362 (9)0.0414 (8)0.0234 (8)0.0020 (7)−0.0038 (6)−0.0001 (6)
C160.0377 (9)0.0345 (8)0.0233 (8)0.0044 (7)−0.0038 (6)−0.0001 (6)
C170.0237 (7)0.0187 (6)0.0214 (7)−0.0014 (5)0.0034 (6)0.0032 (5)
C180.0194 (7)0.0209 (6)0.0240 (7)−0.0002 (5)−0.0025 (5)0.0057 (5)
C190.0177 (7)0.0194 (6)0.0279 (7)0.0008 (5)0.0035 (6)0.0050 (5)
C200.0174 (6)0.0188 (6)0.0224 (7)−0.0012 (5)0.0022 (5)0.0047 (5)
C210.0184 (7)0.0227 (6)0.0236 (7)0.0008 (5)0.0004 (5)0.0064 (5)
C220.0201 (7)0.0195 (6)0.0273 (7)0.0030 (5)0.0050 (6)0.0052 (5)
C230.0205 (7)0.0226 (6)0.0247 (7)0.0009 (5)0.0046 (6)0.0055 (5)
C240.0196 (7)0.0244 (6)0.0209 (7)0.0009 (5)0.0041 (5)0.0022 (5)
C250.0244 (7)0.0235 (6)0.0247 (7)0.0026 (5)0.0034 (6)0.0019 (5)
C260.0255 (7)0.0250 (6)0.0237 (7)0.0001 (5)0.0023 (6)−0.0015 (5)
C270.0245 (7)0.0298 (7)0.0208 (7)0.0002 (6)0.0033 (6)0.0012 (6)
C280.0275 (8)0.0251 (6)0.0224 (7)0.0028 (6)0.0005 (6)0.0033 (5)
C290.0260 (7)0.0239 (6)0.0226 (7)−0.0002 (5)0.0013 (6)0.0012 (5)
C300.0342 (9)0.0367 (8)0.0262 (8)0.0037 (7)−0.0020 (6)−0.0006 (6)
O1—C21.3658 (15)C15—H15A0.9800
O1—C11.4289 (16)C15—H15B0.9800
O2—C81.2273 (14)C15—H15C0.9800
O3—C171.3663 (15)C16—H16A0.9800
O3—C161.4290 (16)C16—H16B0.9800
O4—C231.2269 (14)C16—H16C0.9800
C1—H1A0.9800C17—C221.3898 (18)
C1—H1B0.9800C17—C181.3936 (17)
C1—H1C0.9800C18—C191.3860 (17)
C2—C71.3897 (18)C18—H180.9500
C2—C31.3935 (17)C19—C201.3908 (17)
C3—C41.3863 (17)C19—H190.9500
C3—H30.9500C20—C211.4022 (17)
C4—C51.3910 (17)C20—C231.4915 (17)
C4—H40.9500C21—C221.3785 (17)
C5—C61.4000 (16)C21—H210.9500
C5—C81.4886 (17)C22—H220.9500
C6—C71.3806 (17)C23—C241.5152 (18)
C6—H60.9500C24—C251.5317 (16)
C7—H70.9500C24—C291.5427 (17)
C8—C91.5142 (18)C24—H241.0000
C9—C101.5251 (17)C25—C261.5264 (18)
C9—C141.5418 (17)C25—H25A0.9900
C9—H91.0000C25—H25B0.9900
C10—C111.5290 (18)C26—C271.5289 (17)
C10—H10A0.9900C26—H26A0.9900
C10—H10B0.9900C26—H26B0.9900
C11—C121.5266 (18)C27—C301.5244 (18)
C11—H11A0.9900C27—C281.5283 (17)
C11—H11B0.9900C27—H271.0000
C12—C151.5252 (18)C28—C291.5277 (17)
C12—C131.5251 (18)C28—H28A0.9900
C12—H121.0000C28—H28B0.9900
C13—C141.5256 (18)C29—H29A0.9900
C13—H13A0.9900C29—H29B0.9900
C13—H13B0.9900C30—H30A0.9800
C14—H14A0.9900C30—H30B0.9800
C14—H14B0.9900C30—H30C0.9800
C2—O1—C1117.19 (10)H15B—C15—H15C109.5
C17—O3—C16117.13 (10)O3—C16—H16A109.5
O1—C1—H1A109.5O3—C16—H16B109.5
O1—C1—H1B109.5H16A—C16—H16B109.5
H1A—C1—H1B109.5O3—C16—H16C109.5
O1—C1—H1C109.5H16A—C16—H16C109.5
H1A—C1—H1C109.5H16B—C16—H16C109.5
H1B—C1—H1C109.5O3—C17—C22115.81 (11)
O1—C2—C7115.38 (11)O3—C17—C18124.01 (12)
O1—C2—C3124.43 (12)C22—C17—C18120.19 (12)
C7—C2—C3120.18 (12)C19—C18—C17118.95 (12)
C4—C3—C2118.62 (12)C19—C18—H18120.5
C4—C3—H3120.7C17—C18—H18120.5
C2—C3—H3120.7C18—C19—C20121.69 (11)
C3—C4—C5122.11 (11)C18—C19—H19119.2
C3—C4—H4118.9C20—C19—H19119.2
C5—C4—H4118.9C19—C20—C21118.35 (12)
C4—C5—C6118.18 (12)C19—C20—C23118.46 (11)
C4—C5—C8118.67 (11)C21—C20—C23123.16 (12)
C6—C5—C8123.13 (12)C22—C21—C20120.54 (12)
C7—C6—C5120.43 (12)C22—C21—H21119.7
C7—C6—H6119.8C20—C21—H21119.7
C5—C6—H6119.8C21—C22—C17120.26 (11)
C6—C7—C2120.42 (11)C21—C22—H22119.9
C6—C7—H7119.8C17—C22—H22119.9
C2—C7—H7119.8O4—C23—C20119.73 (12)
O2—C8—C5119.42 (12)O4—C23—C24120.28 (12)
O2—C8—C9119.92 (11)C20—C23—C24119.99 (10)
C5—C8—C9120.59 (10)C23—C24—C25111.55 (10)
C8—C9—C10112.24 (10)C23—C24—C29109.11 (11)
C8—C9—C14106.83 (11)C25—C24—C29110.09 (10)
C10—C9—C14110.54 (11)C23—C24—H24108.7
C8—C9—H9109.1C25—C24—H24108.7
C10—C9—H9109.1C29—C24—H24108.7
C14—C9—H9109.1C26—C25—C24111.27 (10)
C9—C10—C11111.49 (10)C26—C25—H25A109.4
C9—C10—H10A109.3C24—C25—H25A109.4
C11—C10—H10A109.3C26—C25—H25B109.4
C9—C10—H10B109.3C24—C25—H25B109.4
C11—C10—H10B109.3H25A—C25—H25B108.0
H10A—C10—H10B108.0C25—C26—C27111.83 (11)
C12—C11—C10111.75 (11)C25—C26—H26A109.2
C12—C11—H11A109.3C27—C26—H26A109.3
C10—C11—H11A109.3C25—C26—H26B109.3
C12—C11—H11B109.3C27—C26—H26B109.3
C10—C11—H11B109.3H26A—C26—H26B107.9
H11A—C11—H11B107.9C30—C27—C28111.83 (10)
C15—C12—C13111.66 (11)C30—C27—C26111.76 (11)
C15—C12—C11111.45 (12)C28—C27—C26109.44 (11)
C13—C12—C11109.48 (11)C30—C27—H27107.9
C15—C12—H12108.0C28—C27—H27107.9
C13—C12—H12108.0C26—C27—H27107.9
C11—C12—H12108.0C29—C28—C27112.45 (10)
C12—C13—C14112.18 (10)C29—C28—H28A109.1
C12—C13—H13A109.2C27—C28—H28A109.1
C14—C13—H13A109.2C29—C28—H28B109.1
C12—C13—H13B109.2C27—C28—H28B109.1
C14—C13—H13B109.2H28A—C28—H28B107.8
H13A—C13—H13B107.9C28—C29—C24111.02 (11)
C13—C14—C9111.44 (11)C28—C29—H29A109.4
C13—C14—H14A109.3C24—C29—H29A109.4
C9—C14—H14A109.3C28—C29—H29B109.4
C13—C14—H14B109.3C24—C29—H29B109.4
C9—C14—H14B109.3H29A—C29—H29B108.0
H14A—C14—H14B108.0C27—C30—H30A109.5
C12—C15—H15A109.5C27—C30—H30B109.5
C12—C15—H15B109.5H30A—C30—H30B109.5
H15A—C15—H15B109.5C27—C30—H30C109.5
C12—C15—H15C109.5H30A—C30—H30C109.5
H15A—C15—H15C109.5H30B—C30—H30C109.5
C1—O1—C2—C7173.31 (10)C16—O3—C17—C22177.02 (11)
C1—O1—C2—C3−7.90 (17)C16—O3—C17—C18−3.19 (17)
O1—C2—C3—C4179.14 (11)O3—C17—C18—C19179.81 (11)
C7—C2—C3—C4−2.13 (17)C22—C17—C18—C19−0.41 (18)
C2—C3—C4—C51.44 (17)C17—C18—C19—C201.11 (18)
C3—C4—C5—C60.71 (17)C18—C19—C20—C21−0.56 (18)
C3—C4—C5—C8−177.36 (10)C18—C19—C20—C23177.42 (11)
C4—C5—C6—C7−2.21 (17)C19—C20—C21—C22−0.68 (18)
C8—C5—C6—C7175.77 (11)C23—C20—C21—C22−178.56 (11)
C5—C6—C7—C21.54 (17)C20—C21—C22—C171.37 (18)
O1—C2—C7—C6179.51 (10)O3—C17—C22—C21178.99 (11)
C3—C2—C7—C60.67 (17)C18—C17—C22—C21−0.81 (18)
C4—C5—C8—O221.98 (17)C19—C20—C23—O412.43 (18)
C6—C5—C8—O2−155.99 (12)C21—C20—C23—O4−169.69 (12)
C4—C5—C8—C9−155.03 (11)C19—C20—C23—C24−167.66 (11)
C6—C5—C8—C927.00 (17)C21—C20—C23—C2410.22 (18)
O2—C8—C9—C1039.30 (16)O4—C23—C24—C25−29.70 (16)
C5—C8—C9—C10−143.71 (11)C20—C23—C24—C25150.39 (11)
O2—C8—C9—C14−82.01 (14)O4—C23—C24—C2992.15 (14)
C5—C8—C9—C1494.98 (13)C20—C23—C24—C29−87.76 (13)
C8—C9—C10—C11−173.66 (11)C23—C24—C25—C26177.09 (10)
C14—C9—C10—C11−54.51 (14)C29—C24—C25—C2655.81 (14)
C9—C10—C11—C1256.90 (15)C24—C25—C26—C27−57.41 (14)
C10—C11—C12—C15179.37 (10)C25—C26—C27—C30−179.46 (10)
C10—C11—C12—C13−56.60 (14)C25—C26—C27—C2856.11 (14)
C15—C12—C13—C14−179.84 (11)C30—C27—C28—C29179.88 (11)
C11—C12—C13—C1456.25 (14)C26—C27—C28—C29−55.74 (14)
C12—C13—C14—C9−55.65 (14)C27—C28—C29—C2456.02 (14)
C8—C9—C14—C13176.27 (10)C23—C24—C29—C28−177.67 (10)
C10—C9—C14—C1353.89 (13)C25—C24—C29—C28−54.94 (13)
D—H···AD—HH···AD···AD—H···A
C9—H9···O2i1.002.573.4694 (18)150
C24—H24···O4ii1.002.603.5244 (18)154
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A DA D—H⋯A
C9—H9⋯O2i 1.002.573.4694 (18)150
C24—H24⋯O4ii 1.002.603.5244 (18)154

Symmetry codes: (i) ; (ii) .

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