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The crystal structure of (S)-(+)-ibuprofen, C13H18O2, has been redetermined. It crystallizes in the monoclinic space group P21 with two mol­ecules in the asymmetric unit, giving a cyclic hydrogen-bonded dimer. All the H atoms were located from difference maps and refined isotropically.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680301451X/cf6266sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680301451X/cf6266Isup2.hkl
Contains datablock I

CCDC reference: 222894

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.038
  • wR factor = 0.105
  • Data-to-parameter ratio = 7.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT390_ALERT_3_B Deviating Methyl C13B X-C-H Bond Angle ...... 98.00 Deg.
Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.00 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.28 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.75 Ratio PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C1A PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C11A PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C1B PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C11B PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT351_ALERT_3_C Long C-H Bond (0.96A) C12A - H131 = 1.12 Ang. PLAT351_ALERT_3_C Long C-H Bond (0.96A) C3B - H3B3 = 1.14 Ang. PLAT351_ALERT_3_C Long C-H Bond (0.96A) C12B - H126 = 1.12 Ang. PLAT355_ALERT_3_C Long O-H Bond (0.82A) O1B - H1BO = 1.07 Ang. PLAT390_ALERT_3_C Deviating Methyl C12B X-C-H Bond Angle ...... 117.00 Deg. PLAT390_ALERT_3_C Deviating Methyl C12B X-C-H Bond Angle ...... 100.00 Deg. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 8 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C13 H18 O2
Alert level G 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 26.96 From the CIF: _reflns_number_total 2910 Count of symmetry unique reflns 2909 Completeness (_total/calc) 100.03% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 17 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 11 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

The structure of racemic ibuprofen (IBP), (I), has been well described both by X-ray diffraction at 298 K (McConnell, 1974) and single-crystal pulsed neutron diffraction at 100 K (Shankland et al., 1997). The structure of (S)-ibuprofen has also been solved by X-ray diffraction (Freer et al., 1993). However, in contrast to the racemate, the quality and paucity of data did not allow the determination of the positions of the H atoms. It should be noted that the lack of this information is a serious obstacle for a logical classification of the hydrogen-bond topology of the compound, and for the calculation of crystal-lattice energy by methods which are sensitive to the geometry of hydrogen bonding (e.g. Gavezzotti & Filippini, 1997). With this background, the main aim of this work has been to find and refine the positions of the H atoms.

A view of the two crystallographically independent (S)-IBP molecules, with the atomic numbering, is presented in Fig. 1. The parameters of the hydrogen-bond geometry for both the racemic and S-enantiomer IBP are shown in Table 1 (Taylor & Kennard, 1982). As there are two independent molecules in the asymmetric unit, the two hydrogen bonds are not geometrically equivalent; one of them is shorter than the other. Comparison of these data gives the following conclusions: (a) the hydrogen bond in the racemate is more linear than in the S-enantiomer; (b) one of the O···O distances in (S)-IBP is essentially the same as that in the racemate, but the other is longer; (c) the H···O distance in the racemate is an average of the analogous parameters of the S-enantiomer. The conformations of the S-enantiomer molecules are different; the main parameters characterizing these differences are presented in Table 2, together with corresponding ones for the racemate. As can be seen, molecule A in the S-enantiomer structure has approximately the same conformation as the IBP molecule in the racemate.

Experimental top

(S)-IBP single crystals were grown by slow evaporation from an n-heptanol solution.

Computing details top

Data collection: CAD-4-PC Software (Enraf–Nonius, 1992); cell refinement: CELDIM in CAD-4-PC Software; data reduction: XCAD4 (McArdle & Higgins, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: OSCAIL (Version 9; McArdle, 1993).

Figures top
[Figure 1] Fig. 1. A view of the (S)-(+)-ibuprofen dimer with the atomic numbering scheme. Displacement ellipsoids are drawn at the 20% probability level.
(I) top
Crystal data top
C13H18O2F(000) = 448
Mr = 206.27Dx = 1.098 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71069 Å
a = 12.456 (4) ÅCell parameters from 25 reflections
b = 8.0362 (11) Åθ = 14–20°
c = 13.533 (3) ŵ = 0.07 mm1
β = 112.86 (2)°T = 298 K
V = 1248.2 (5) Å3Block, colourless
Z = 40.40 × 0.40 × 0.30 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.019
Radiation source: fine-focus sealed tubeθmax = 27.0°, θmin = 1.6°
Graphite monochromatorh = 015
ω–2θ scansk = 110
3086 measured reflectionsl = 1715
2910 independent reflections3 standard reflections every 120 min
1683 reflections with I > 2σ(I) intensity decay: 2%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039All H-atom parameters refined
wR(F2) = 0.105 w = 1/[σ2(Fo2) + (0.0583P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max = 0.002
2910 reflectionsΔρmax = 0.12 e Å3
416 parametersΔρmin = 0.11 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.016 (3)
Crystal data top
C13H18O2V = 1248.2 (5) Å3
Mr = 206.27Z = 4
Monoclinic, P21Mo Kα radiation
a = 12.456 (4) ŵ = 0.07 mm1
b = 8.0362 (11) ÅT = 298 K
c = 13.533 (3) Å0.40 × 0.40 × 0.30 mm
β = 112.86 (2)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.019
3086 measured reflections3 standard reflections every 120 min
2910 independent reflections intensity decay: 2%
1683 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0391 restraint
wR(F2) = 0.105All H-atom parameters refined
S = 0.98Δρmax = 0.12 e Å3
2910 reflectionsΔρmin = 0.11 e Å3
416 parameters
Special details top

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

10.1787 (0.0112) x + 4.6284 (0.0096) y − 4.5783 (0.0166) z = 3.3305 (0.0116)

* −0.0072 (0.0022) C4A * 0.0049 (0.0026) C5A * 0.0010 (0.0026) C6A * −0.0047 (0.0023) C7A * 0.0024 (0.0024) C8A * 0.0036 (0.0023) C9A 1.4672 (0.0056) C1A 0.0366 (0.0051) C2A −0.7949 (0.0064) C3A 2.1128 (0.0059) O1A 2.0110 (0.0057) O2A −0.0771 (0.0056) C10A −1.4843 (0.0060) C11A −1.4790 (0.0092) C12A −2.2935 (0.0070) C13A

Rms deviation of fitted atoms = 0.0044

9.9282 (0.0098) x + 4.8474 (0.0078) y − 4.5545 (0.0147) z = 9.7391 (0.0062)

Angle to previous plane (with approximate e.s.d.) = 1.98 (0.18)

* 0.0096 (0.0019) C4B * −0.0063 (0.0021) C5B * −0.0037 (0.0021) C6B * 0.0105 (0.0019) C7B * −0.0073 (0.0020) C8B * −0.0027 (0.0020) C9B −1.4004 (0.0051) C1B 0.0314 (0.0046) C2B 0.7091 (0.0063) C3B −2.0812 (0.0050) O1B −1.8909 (0.0052) O2B 0.0649 (0.0047) C10B 1.4528 (0.0055) C11B 2.4265 (0.0067) C12B 1.3582 (0.0088) C13B

Rms deviation of fitted atoms = 0.0073

Hydrogen bonds with H.·A < r(A) + 2.000 Angstroms and <DHA > 110 °.

D—H d(D—H) d(H.·A) <DHA d(D.·A) A

O1B—H1BO 1.070 1.579 167.64 2.634 O2A

O1A—H1AO 0.937 1.726 168.97 2.651 O2B

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
xyzUiso*/Ueq
C4B0.8401 (2)0.3199 (3)0.0314 (2)0.0497 (7)
O2A0.58499 (19)0.2352 (3)0.10390 (18)0.0757 (6)
O1A0.4640 (2)0.0661 (4)0.2241 (2)0.0890 (8)
O1B0.7685 (2)0.0391 (3)0.04780 (18)0.0710 (6)
O2B0.6486 (2)0.1313 (3)0.16958 (17)0.0840 (7)
C7B0.8336 (2)0.4998 (3)0.2083 (2)0.0493 (7)
C9B0.7668 (2)0.4546 (4)0.0175 (2)0.0547 (7)
C6B0.9054 (3)0.3626 (4)0.2220 (2)0.0604 (8)
C8B0.7632 (2)0.5422 (4)0.1041 (2)0.0548 (7)
C2B0.8429 (3)0.2278 (4)0.0655 (2)0.0590 (8)
C5B0.9085 (3)0.2746 (4)0.1358 (2)0.0599 (8)
C10B0.8355 (3)0.5965 (4)0.3034 (2)0.0614 (8)
C11B0.9402 (3)0.7128 (5)0.3508 (2)0.0688 (9)
C1B0.7446 (3)0.1014 (4)0.0998 (2)0.0547 (7)
C12B0.9347 (5)0.8545 (7)0.2759 (4)0.1068 (17)
C3B0.9591 (3)0.1463 (6)0.0477 (4)0.0835 (11)
C13B0.9486 (6)0.7781 (7)0.4595 (4)0.1045 (15)
H3B30.990 (3)0.047 (6)0.017 (3)0.117 (14)*
H1330.170 (5)0.953 (8)0.765 (4)0.16 (2)*
H1230.363 (5)1.006 (10)0.537 (4)0.19 (3)*
H1BO0.688 (4)0.106 (6)0.077 (3)0.113 (13)*
H1320.225 (4)0.765 (7)0.783 (4)0.129 (18)*
H1310.328 (4)0.925 (7)0.732 (4)0.16 (2)*
H1260.865 (6)0.933 (12)0.286 (6)0.24 (4)*
H3B20.949 (2)0.094 (4)0.118 (2)0.072 (9)*
H2B0.821 (2)0.309 (4)0.128 (2)0.064 (8)*
H3B11.020 (4)0.236 (8)0.031 (4)0.144 (18)*
H1250.913 (4)0.826 (6)0.200 (4)0.114 (14)*
H1241.015 (5)0.917 (9)0.310 (4)0.16 (2)*
H1030.840 (2)0.513 (4)0.360 (2)0.068 (9)*
H1040.761 (3)0.665 (4)0.279 (2)0.065 (9)*
H6B0.957 (3)0.326 (4)0.298 (3)0.075 (10)*
H1360.883 (4)0.850 (7)0.435 (4)0.14 (2)*
H8B0.712 (3)0.632 (5)0.093 (2)0.073 (9)*
H1341.009 (3)0.841 (5)0.486 (3)0.074 (11)*
H5B0.966 (2)0.183 (4)0.152 (2)0.071 (9)*
H9B0.712 (3)0.480 (5)0.053 (3)0.093 (11)*
H1350.949 (5)0.679 (10)0.516 (5)0.19 (3)*
H11B1.020 (3)0.655 (4)0.3544 (19)0.065 (8)*
H3A30.332 (3)0.522 (6)0.127 (3)0.108 (12)*
H11A0.195 (4)0.741 (6)0.642 (3)0.111 (14)*
H1010.434 (3)0.741 (5)0.577 (3)0.088 (12)*
H3A20.403 (3)0.385 (6)0.050 (3)0.104 (14)*
H1020.348 (3)0.600 (6)0.645 (3)0.115 (15)*
H1210.298 (3)0.904 (6)0.474 (3)0.108 (12)*
H1220.210 (4)1.024 (7)0.584 (3)0.122 (14)*
H6A0.257 (3)0.404 (6)0.563 (3)0.105 (12)*
H2A0.326 (3)0.265 (5)0.217 (3)0.096 (12)*
H8A0.500 (3)0.738 (5)0.376 (2)0.074 (9)*
H9A0.500 (3)0.598 (4)0.227 (3)0.058 (8)*
H5A0.271 (3)0.283 (5)0.398 (2)0.074 (10)*
H1AO0.533 (4)0.007 (8)0.208 (4)0.16 (2)*
H3A10.481 (4)0.502 (6)0.073 (3)0.131 (16)*
C1A0.4879 (3)0.2052 (4)0.1705 (2)0.0613 (8)
C2A0.3900 (3)0.3274 (4)0.1995 (3)0.0680 (9)
C3A0.4028 (4)0.4412 (7)0.1044 (4)0.0899 (13)
C4A0.3837 (2)0.4215 (4)0.2990 (2)0.0592 (8)
C5A0.3135 (3)0.3645 (5)0.4000 (3)0.0776 (10)
C6A0.3095 (3)0.4468 (5)0.4913 (3)0.0795 (10)
C7A0.3752 (3)0.5870 (4)0.4856 (3)0.0666 (9)
C8A0.4460 (3)0.6415 (5)0.3850 (3)0.0685 (9)
C9A0.4501 (3)0.5605 (4)0.2941 (3)0.0659 (9)
C10A0.3649 (4)0.6796 (6)0.5864 (3)0.0820 (12)
C11A0.2651 (3)0.8032 (5)0.6258 (3)0.0756 (10)
C13A0.2856 (5)0.9476 (6)0.5496 (4)0.0920 (13)
C12A0.2441 (5)0.8664 (9)0.7376 (3)0.1028 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C4B0.0532 (14)0.0418 (16)0.0556 (16)0.0049 (13)0.0229 (12)0.0050 (13)
O2A0.0602 (12)0.0611 (14)0.0891 (14)0.0027 (11)0.0106 (11)0.0094 (12)
O1A0.0719 (16)0.0732 (17)0.0998 (18)0.0059 (14)0.0094 (14)0.0200 (15)
O1B0.0699 (14)0.0505 (13)0.0825 (14)0.0005 (11)0.0186 (11)0.0060 (12)
O2B0.0822 (14)0.0658 (15)0.0799 (14)0.0034 (13)0.0051 (13)0.0127 (13)
C7B0.0488 (14)0.0476 (16)0.0541 (16)0.0070 (13)0.0227 (12)0.0038 (14)
C9B0.0545 (16)0.0519 (17)0.0523 (16)0.0047 (15)0.0148 (13)0.0004 (14)
C6B0.0727 (19)0.0566 (18)0.0504 (17)0.0013 (17)0.0224 (15)0.0047 (16)
C8B0.0554 (16)0.0487 (16)0.0566 (16)0.0090 (15)0.0178 (13)0.0005 (14)
C2B0.0716 (19)0.0511 (19)0.0646 (18)0.0018 (16)0.0379 (15)0.0023 (16)
C5B0.0644 (17)0.0454 (17)0.0676 (19)0.0142 (15)0.0231 (15)0.0061 (15)
C10B0.0675 (19)0.064 (2)0.0547 (16)0.0061 (17)0.0259 (14)0.0025 (17)
C11B0.075 (2)0.065 (2)0.0639 (19)0.0088 (18)0.0246 (16)0.0154 (17)
C1B0.0708 (18)0.0455 (17)0.0530 (16)0.0069 (15)0.0296 (15)0.0022 (14)
C12B0.137 (4)0.098 (4)0.086 (3)0.047 (3)0.043 (3)0.009 (3)
C3B0.079 (2)0.080 (3)0.111 (3)0.006 (2)0.058 (2)0.028 (3)
C13B0.134 (4)0.093 (3)0.077 (3)0.022 (4)0.030 (3)0.030 (3)
C1A0.0580 (18)0.059 (2)0.0647 (18)0.0051 (16)0.0210 (16)0.0113 (18)
C2A0.0517 (17)0.069 (2)0.084 (2)0.0060 (17)0.0268 (16)0.0114 (19)
C3A0.096 (3)0.105 (3)0.085 (3)0.027 (3)0.053 (2)0.014 (3)
C4A0.0421 (14)0.059 (2)0.0703 (19)0.0021 (14)0.0149 (13)0.0007 (16)
C5A0.076 (2)0.059 (2)0.087 (3)0.014 (2)0.0197 (19)0.003 (2)
C6A0.088 (2)0.069 (2)0.064 (2)0.002 (2)0.0107 (18)0.006 (2)
C7A0.0706 (19)0.063 (2)0.069 (2)0.0111 (17)0.0302 (16)0.0028 (18)
C8A0.0582 (18)0.068 (2)0.073 (2)0.0080 (18)0.0184 (16)0.0084 (19)
C9A0.0570 (17)0.065 (2)0.0634 (19)0.0084 (17)0.0098 (15)0.0041 (18)
C10A0.089 (3)0.093 (3)0.071 (2)0.017 (2)0.038 (2)0.006 (2)
C11A0.073 (2)0.086 (3)0.0643 (19)0.000 (2)0.0234 (16)0.007 (2)
C13A0.106 (3)0.084 (3)0.084 (3)0.013 (3)0.036 (3)0.003 (2)
C12A0.105 (3)0.126 (4)0.073 (2)0.010 (3)0.030 (2)0.022 (3)
Geometric parameters (Å, º) top
C4B—C9B1.382 (4)C13B—H1360.95 (5)
C4B—C5B1.385 (4)C13B—H1340.86 (4)
C4B—C2B1.517 (4)C13B—H1351.10 (7)
O2A—C1A1.219 (3)C1A—C2A1.496 (5)
O1A—C1A1.302 (4)C2A—C4A1.519 (4)
O1A—H1AO0.94 (6)C2A—C3A1.536 (6)
O1B—C1B1.302 (4)C2A—H2A0.89 (4)
O1B—H1BO1.07 (5)C3A—H3A31.05 (4)
O2B—C1B1.226 (3)C3A—H3A20.87 (4)
C7B—C8B1.383 (4)C3A—H3A11.03 (5)
C7B—C6B1.386 (4)C4A—C9A1.377 (4)
C7B—C10B1.495 (4)C4A—C5A1.384 (4)
C9B—C8B1.382 (4)C5A—C6A1.385 (5)
C9B—H9B0.96 (3)C5A—H5A0.85 (4)
C6B—C5B1.378 (4)C6A—C7A1.376 (5)
C6B—H6B1.03 (4)C6A—H6A1.00 (4)
C8B—H8B0.93 (4)C7A—C8A1.375 (4)
C2B—C1B1.518 (4)C7A—C10A1.515 (5)
C2B—C3B1.521 (5)C8A—C9A1.374 (4)
C2B—H2B1.01 (3)C8A—H8A1.00 (4)
C5B—H5B0.99 (3)C9A—H9A0.93 (3)
C10B—C11B1.529 (4)C10A—C11A1.516 (6)
C10B—H1031.00 (3)C10A—H1010.95 (4)
C10B—H1041.01 (3)C10A—H1020.97 (5)
C11B—C12B1.508 (6)C11A—C13A1.506 (6)
C11B—C13B1.526 (5)C11A—C12A1.520 (5)
C11B—H11B1.08 (3)C11A—H11A0.95 (4)
C12B—H1261.12 (8)C13A—H1231.03 (6)
C12B—H1250.98 (4)C13A—H1211.04 (4)
C12B—H1241.05 (6)C13A—H1221.06 (5)
C3B—H3B31.14 (5)C12A—H1331.09 (6)
C3B—H3B21.00 (3)C12A—H1320.99 (6)
C3B—H3B11.00 (6)C12A—H1311.12 (5)
C9B—C4B—C5B117.1 (3)H134—C13B—H135112 (4)
C9B—C4B—C2B120.0 (3)O2A—C1A—O1A121.9 (3)
C5B—C4B—C2B122.8 (3)O2A—C1A—C2A122.5 (3)
C1A—O1A—H1AO109 (3)O1A—C1A—C2A115.5 (3)
C1B—O1B—H1BO105 (2)C1A—C2A—C4A108.3 (3)
C8B—C7B—C6B116.9 (3)C1A—C2A—C3A111.3 (3)
C8B—C7B—C10B122.8 (3)C4A—C2A—C3A113.5 (3)
C6B—C7B—C10B120.3 (3)C1A—C2A—H2A105 (3)
C8B—C9B—C4B121.4 (3)C4A—C2A—H2A108 (2)
C8B—C9B—H9B120 (2)C3A—C2A—H2A110 (2)
C4B—C9B—H9B119 (2)C2A—C3A—H3A3109 (2)
C5B—C6B—C7B121.7 (3)C2A—C3A—H3A2112 (3)
C5B—C6B—H6B119.4 (19)H3A3—C3A—H3A2107 (3)
C7B—C6B—H6B119.0 (19)C2A—C3A—H3A1114 (2)
C9B—C8B—C7B121.5 (3)H3A3—C3A—H3A1113 (4)
C9B—C8B—H8B119.7 (18)H3A2—C3A—H3A1102 (3)
C7B—C8B—H8B118.8 (17)C9A—C4A—C5A116.9 (3)
C4B—C2B—C1B107.7 (2)C9A—C4A—C2A122.6 (3)
C4B—C2B—C3B114.4 (3)C5A—C4A—C2A120.4 (3)
C1B—C2B—C3B111.4 (3)C4A—C5A—C6A120.9 (4)
C4B—C2B—H2B108.2 (16)C4A—C5A—H5A113 (2)
C1B—C2B—H2B104.5 (16)C6A—C5A—H5A126 (2)
C3B—C2B—H2B110.1 (15)C7A—C6A—C5A121.7 (4)
C6B—C5B—C4B121.3 (3)C7A—C6A—H6A119 (2)
C6B—C5B—H5B116.7 (16)C5A—C6A—H6A119 (2)
C4B—C5B—H5B121.8 (16)C8A—C7A—C6A117.1 (3)
C7B—C10B—C11B113.9 (3)C8A—C7A—C10A122.2 (3)
C7B—C10B—H103106.8 (17)C6A—C7A—C10A120.7 (4)
C11B—C10B—H103107.5 (16)C9A—C8A—C7A121.4 (3)
C7B—C10B—H104107.4 (16)C9A—C8A—H8A118.2 (17)
C11B—C10B—H104109.0 (18)C7A—C8A—H8A120.2 (17)
H103—C10B—H104112 (2)C8A—C9A—C4A121.9 (3)
C12B—C11B—C13B110.9 (4)C8A—C9A—H9A120.1 (18)
C12B—C11B—C10B111.8 (3)C4A—C9A—H9A118.0 (18)
C13B—C11B—C10B110.1 (4)C7A—C10A—C11A114.2 (3)
C12B—C11B—H11B98.8 (16)C7A—C10A—H101112 (2)
C13B—C11B—H11B112.7 (14)C11A—C10A—H101106 (2)
C10B—C11B—H11B112.2 (17)C7A—C10A—H102109 (3)
O2B—C1B—O1B122.4 (3)C11A—C10A—H102105 (2)
O2B—C1B—C2B122.3 (3)H101—C10A—H102110 (3)
O1B—C1B—C2B115.3 (3)C13A—C11A—C10A111.5 (4)
C11B—C12B—H126100 (4)C13A—C11A—C12A110.0 (4)
C11B—C12B—H125117 (3)C10A—C11A—C12A111.7 (4)
H126—C12B—H125110 (4)C13A—C11A—H11A117 (3)
C11B—C12B—H124106 (3)C10A—C11A—H11A107 (3)
H126—C12B—H124109 (5)C12A—C11A—H11A99 (2)
H125—C12B—H124113 (4)C11A—C13A—H123112 (4)
C2B—C3B—H3B3116 (2)C11A—C13A—H121110 (3)
C2B—C3B—H3B2105.4 (17)H123—C13A—H121102 (4)
H3B3—C3B—H3B2109 (3)C11A—C13A—H122105 (2)
C2B—C3B—H3B1108 (3)H123—C13A—H122115 (5)
H3B3—C3B—H3B1109 (4)H121—C13A—H122114 (3)
H3B2—C3B—H3B1109 (3)C11A—C12A—H133110 (3)
C11B—C13B—H13698 (3)C11A—C12A—H132104 (3)
C11B—C13B—H134109 (3)H133—C12A—H132111 (4)
H136—C13B—H134107 (4)C11A—C12A—H131106 (2)
C11B—C13B—H135114 (3)H133—C12A—H131113 (4)
H136—C13B—H135117 (4)H132—C12A—H131112 (4)
C5B—C4B—C9B—C8B1.1 (4)O2A—C1A—C2A—C4A95.9 (4)
C2B—C4B—C9B—C8B179.3 (3)O1A—C1A—C2A—C4A81.7 (4)
C8B—C7B—C6B—C5B1.4 (4)O2A—C1A—C2A—C3A29.6 (5)
C10B—C7B—C6B—C5B177.7 (3)O1A—C1A—C2A—C3A152.8 (3)
C4B—C9B—C8B—C7B0.5 (4)C1A—C2A—C4A—C9A85.5 (4)
C6B—C7B—C8B—C9B1.7 (4)C3A—C2A—C4A—C9A38.7 (4)
C10B—C7B—C8B—C9B177.3 (3)C1A—C2A—C4A—C5A91.4 (4)
C9B—C4B—C2B—C1B84.3 (3)C3A—C2A—C4A—C5A144.4 (4)
C5B—C4B—C2B—C1B95.3 (3)C9A—C4A—C5A—C6A1.2 (5)
C9B—C4B—C2B—C3B151.2 (3)C2A—C4A—C5A—C6A178.3 (3)
C5B—C4B—C2B—C3B29.1 (4)C4A—C5A—C6A—C7A0.5 (6)
C7B—C6B—C5B—C4B0.2 (5)C5A—C6A—C7A—C8A0.4 (5)
C9B—C4B—C5B—C6B1.4 (4)C5A—C6A—C7A—C10A177.0 (3)
C2B—C4B—C5B—C6B178.9 (3)C6A—C7A—C8A—C9A0.5 (5)
C8B—C7B—C10B—C11B101.8 (3)C10A—C7A—C8A—C9A176.8 (3)
C6B—C7B—C10B—C11B77.2 (4)C7A—C8A—C9A—C4A0.2 (5)
C7B—C10B—C11B—C12B68.0 (5)C5A—C4A—C9A—C8A1.1 (5)
C7B—C10B—C11B—C13B168.3 (4)C2A—C4A—C9A—C8A178.1 (3)
C4B—C2B—C1B—O2B94.6 (3)C8A—C7A—C10A—C11A93.2 (5)
C3B—C2B—C1B—O2B139.2 (3)C6A—C7A—C10A—C11A84.0 (5)
C4B—C2B—C1B—O1B83.5 (3)C7A—C10A—C11A—C13A67.9 (5)
C3B—C2B—C1B—O1B42.7 (4)C7A—C10A—C11A—C12A168.7 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1B—H1BO···O2A1.07 (5)1.58 (5)2.634 (4)168 (4)
O1A—H1AO···O2B0.94 (5)1.73 (6)2.651 (4)169 (5)

Experimental details

Crystal data
Chemical formulaC13H18O2
Mr206.27
Crystal system, space groupMonoclinic, P21
Temperature (K)298
a, b, c (Å)12.456 (4), 8.0362 (11), 13.533 (3)
β (°) 112.86 (2)
V3)1248.2 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.40 × 0.40 × 0.30
Data collection
DiffractometerEnraf-Nonius CAD-4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
3086, 2910, 1683
Rint0.019
(sin θ/λ)max1)0.638
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.105, 0.98
No. of reflections2910
No. of parameters416
No. of restraints1
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.12, 0.11

Computer programs: CAD-4-PC Software (Enraf–Nonius, 1992), CELDIM in CAD-4-PC Software, XCAD4 (McArdle & Higgins, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEX (McArdle, 1995), OSCAIL (Version 9; McArdle, 1993).

Hydrogen-bond geometry (Å, °) in the crystal structures of the title compound and of its racemate top
D—H···AD—HH···AD···AD—H···A
O1A—H1AO···O2B0.94 (5)1.73 (6)2.651 (4)169 (5)
O1B—H1BO···O2A1.07 (5)1.58 (5)2.634 (4)168 (4)
O2—H2O···O1i,a0.963 (13)1.664 (10)2.627 (7)179.5 (7)
Symmetry code: (i) 1 − x, 1 − y, 1 − z. Reference: (a) Freer et al. (1993).
Geometrical and conformational parameters (Å, °) of (S)- and racemic IBP top
(S)-IBP(S)-IBPracemic IBP
AB
C5—C4—C2—C3144.4 (4)-29.1 (4)140.9 (4)
C7—C10—C11—C12-67.9 (5)68.0 (5)-67.3 (4)
C4—C2—C1—O281.7 (4)-83.5 (3)88.7 (3)
O1—C11.219 (3)1.226 (3)1.222 (3)
O2—C11.302 (4)1.302 (4)1.305 (3)
C1—C21.496 (5)1.518 (4)1.509 (3)
 

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