Redetermination and H-atom refinement of (S)-(+)-ibuprofen. Corrigendum.

Hansen, L.K.; Perlovich, G.L.; Bauer-Brandl, A.

doi:10.1107/S1600536806020575

addenda and errata

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 62| Part 7| July 2006| Pages e17-e18

https://doi.org/10.1107/S1600536806020575

Redetermination and H-atom refinement of (S)-(+)-ibuprofen. Corrigendum.

Lars Kr. Hansen,^a ^* German L. Perlovich ^b,^c and Annette Bauer-Brandl ^b

^aDepartment of Chemistry, University of Tromsø, 9037 Tromsø, Norway, ^bDepartment of Pharmaceutics and Biopharmaceutics, University of Tromsø, 9037 Tromsø, Norway, and ^cInstitute of Solution Chemistry, Russian Academy of Sciences, 153045 Ivanovo, Russian Federation
^*Correspondence e-mail: larsk@chem.uit.no

(Received 8 May 2006; accepted 31 May 2006; online 9 June 2006)

In the paper by Hansen, Perlovich & Bauer-Brandl [Acta Cryst. (2003), E59, o1357–o1358], the coordinates of the R enantiomer of the title compound, C₁₃H₁₈O₂, were incorrectly given instead of those of the S enantiomer. The correct coordinates of the S enantiomer are given here.

1. Comment

In the paper by Hansen et al. (2003 ), the coordinates of the R enantiomer were incorrectly given instead of those of the S enantiomer, (I). The correct coordinates of the S enantiomer are given in the deposited replacement CIF. Molecular geometry parameters are not affected, except for the signs of torsion angles; the correct values are given in Table 1 below for the torsion angles in Table 2 of the previous report (where there was also an error in the atom numbering). Fig. 1 shows the correct structure of the two independent molecules, which form a hydrogen-bonded dimer without crystallographic symmetry.

Figure 1
The structure of the two independent molecules of (I)

. Displacement ellipsoids are shown at the 30% probability level. Hydrogen bonds are shown as dashed lines.

2. Experimental

Table 1
Selected torsion angles (°)

C5B—C4B—C2B—C3B	29.1 (4)
C7B—C10B—C11B—C12B	−68.0 (5)
C4B—C2B—C1B—O1B	83.5 (3)
O1A—C1A—C2A—C4A	−81.7 (4)
C3A—C2A—C4A—C5A	−144.4 (4)
C7A—C10A—C11A—C13A	67.9 (5)

All H atoms were refined freely [C—H = 0.85 (3)–114 (5) Å].

Data collection: CAD-4-PC Software (Enraf–Nonius, 1992 ); cell refinement: CELDIM in CAD-4-PC Software; data reduction: XCAD (McArdle & Higgins, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ); molecular graphics: ORTEX (McArdle, 1995 ); software used to prepare material for publication: OSCAIL (McArdle, 1993 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536806020575/cf2031sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536806020575/cf2031Isup2.hkl

Computing details top

Data collection: CAD-4-PC Software (Enraf–Nonius, 1992); cell refinement: CELDIM in CAD-4-PC Software; data reduction: XCAD (McArdle & Higgins, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: OSCAIL (McArdle, 1993).

S(+)-2-(4-Isobutylphenyl)propionic acid top

Crystal data top

C₁₃H₁₈O₂	D_x = 1.098 Mg m⁻³
M_r = 206.27	Melting point: 323.45 K
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71069 Å
a = 12.456 (4) Å	Cell parameters from 25 reflections
b = 8.0362 (11) Å	θ = 14–20°
c = 13.533 (3) Å	µ = 0.07 mm⁻¹
β = 112.86 (2)°	T = 298 K
V = 1248.2 (5) Å³	Block, colourless
Z = 4	0.40 × 0.40 × 0.30 mm
F(000) = 448

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.019
Radiation source: fine-focus sealed tube	θ_max = 27.0°, θ_min = 1.6°
Graphite monochromator	h = 0→15
ω–2θ scans	k = −1→10
3086 measured reflections	l = −17→15
2910 independent reflections	3 standard reflections every 120 min
1683 reflections with I > 2σ(I)	intensity decay: 2%

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)] = 0.039	All H-atom parameters refined
wR(F²) = 0.104	w = 1/[σ²(F_o²) + (0.0573P)²] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max = 0.004
2910 reflections	Δρ_max = 0.12 e Å⁻³
416 parameters	Δρ_min = −0.11 e Å⁻³
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.016 (3)

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.

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
C4B	0.1599 (2)	0.6802 (3)	0.9686 (2)	0.0497 (7)
O2A	0.41501 (19)	1.2352 (3)	1.10391 (18)	0.0757 (6)
O1A	0.5360 (2)	1.0661 (4)	1.2241 (2)	0.0890 (8)
O1B	0.2315 (2)	1.0390 (3)	1.04780 (18)	0.0710 (6)
O2B	0.3514 (2)	0.8687 (3)	1.16959 (17)	0.0840 (7)
C7B	0.1665 (2)	0.5002 (3)	0.7917 (2)	0.0493 (7)
C9B	0.2332 (2)	0.5454 (4)	0.9825 (2)	0.0547 (7)
C6B	0.0946 (3)	0.6374 (4)	0.7780 (2)	0.0604 (8)
C8B	0.2368 (2)	0.4578 (4)	0.8959 (2)	0.0548 (7)
C2B	0.1572 (3)	0.7722 (4)	1.0655 (2)	0.0590 (8)
C5B	0.0915 (3)	0.7254 (4)	0.8642 (2)	0.0599 (8)
C10B	0.1645 (3)	0.4036 (4)	0.6966 (2)	0.0614 (8)
C11B	0.0598 (3)	0.2872 (5)	0.6492 (2)	0.0689 (9)
C1B	0.2553 (3)	0.8986 (4)	1.0998 (2)	0.0547 (7)
C12B	0.0653 (5)	0.1455 (7)	0.7241 (4)	0.1069 (17)
C3B	0.0409 (3)	0.8537 (6)	1.0477 (4)	0.0835 (11)
C13B	0.0514 (6)	0.2219 (7)	0.5405 (4)	0.1046 (15)
H3B3	0.010 (3)	0.953 (6)	0.983 (3)	0.117 (14)*
H133	0.830 (4)	1.953 (8)	1.765 (4)	0.16 (2)*
H123	0.637 (5)	2.006 (10)	1.537 (4)	0.18 (3)*
H1BO	0.312 (4)	1.106 (6)	1.077 (3)	0.113 (13)*
H132	0.775 (4)	1.765 (7)	1.783 (4)	0.129 (18)*
H131	0.672 (4)	1.925 (7)	1.732 (4)	0.16 (2)*
H126	0.135 (6)	0.067 (12)	0.714 (6)	0.24 (3)*
H3B2	0.051 (2)	0.906 (4)	1.118 (2)	0.072 (9)*
H2B	0.179 (2)	0.691 (4)	1.128 (2)	0.064 (8)*
H3B1	−0.020 (4)	0.764 (8)	1.031 (4)	0.144 (18)*
H125	0.087 (4)	0.174 (6)	0.800 (4)	0.114 (14)*
H124	−0.015 (5)	0.083 (9)	0.690 (4)	0.16 (2)*
H103	0.160 (2)	0.487 (4)	0.640 (2)	0.068 (9)*
H104	0.239 (3)	0.335 (4)	0.721 (2)	0.065 (9)*
H6B	0.043 (3)	0.674 (4)	0.701 (3)	0.075 (9)*
H136	0.117 (4)	0.150 (7)	0.565 (4)	0.14 (2)*
H8B	0.288 (3)	0.368 (5)	0.907 (2)	0.073 (9)*
H134	−0.009 (3)	0.159 (5)	0.515 (3)	0.074 (11)*
H5B	0.034 (2)	0.817 (4)	0.848 (2)	0.071 (9)*
H9B	0.288 (3)	0.520 (5)	1.053 (3)	0.093 (11)*
H135	0.051 (5)	0.321 (10)	0.484 (5)	0.19 (3)*
H11B	−0.020 (3)	0.345 (4)	0.6456 (19)	0.065 (8)*
H3A3	0.668 (3)	1.522 (6)	1.127 (3)	0.108 (12)*
H11A	0.805 (4)	1.741 (6)	1.642 (3)	0.111 (14)*
H101	0.566 (3)	1.741 (5)	1.577 (3)	0.088 (12)*
H3A2	0.597 (3)	1.385 (6)	1.050 (3)	0.104 (14)*
H102	0.652 (3)	1.600 (6)	1.645 (3)	0.114 (15)*
H121	0.702 (3)	1.904 (6)	1.474 (3)	0.108 (12)*
H122	0.790 (4)	2.024 (7)	1.584 (3)	0.122 (14)*
H6A	0.743 (3)	1.404 (6)	1.563 (3)	0.105 (12)*
H2A	0.674 (3)	1.266 (5)	1.217 (3)	0.096 (12)*
H8A	0.500 (3)	1.738 (5)	1.377 (2)	0.074 (9)*
H9A	0.500 (3)	1.598 (4)	1.227 (2)	0.059 (8)*
H5A	0.729 (3)	1.283 (5)	1.398 (2)	0.074 (10)*
H1AO	0.466 (4)	1.007 (8)	1.208 (4)	0.16 (2)*
H3A1	0.519 (4)	1.503 (6)	1.073 (3)	0.132 (16)*
C1A	0.5121 (3)	1.2052 (4)	1.1705 (2)	0.0613 (8)
C2A	0.6101 (3)	1.3274 (4)	1.1995 (3)	0.0680 (9)
C3A	0.5972 (4)	1.4412 (7)	1.1044 (4)	0.0899 (13)
C4A	0.6163 (2)	1.4215 (4)	1.2990 (2)	0.0592 (8)
C5A	0.6865 (3)	1.3646 (5)	1.4000 (3)	0.0776 (10)
C6A	0.6905 (3)	1.4469 (5)	1.4913 (3)	0.0796 (10)
C7A	0.6248 (3)	1.5870 (4)	1.4856 (3)	0.0666 (9)
C8A	0.5540 (3)	1.6416 (5)	1.3850 (3)	0.0685 (9)
C9A	0.5499 (3)	1.5605 (4)	1.2941 (3)	0.0660 (8)
C10A	0.6351 (4)	1.6797 (6)	1.5864 (3)	0.0820 (12)
C11A	0.7349 (3)	1.8032 (5)	1.6258 (3)	0.0756 (10)
C13A	0.7144 (5)	1.9476 (6)	1.5496 (4)	0.0921 (13)
C12A	0.7559 (5)	1.8665 (9)	1.7376 (3)	0.1028 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C4B	0.0532 (14)	0.0418 (16)	0.0556 (16)	−0.0049 (13)	0.0229 (12)	−0.0050 (13)
O2A	0.0602 (12)	0.0612 (14)	0.0891 (14)	−0.0027 (11)	0.0106 (11)	0.0095 (12)
O1A	0.0719 (16)	0.0732 (17)	0.0998 (18)	0.0059 (14)	0.0094 (13)	0.0200 (15)
O1B	0.0699 (14)	0.0505 (13)	0.0826 (14)	0.0005 (11)	0.0186 (11)	0.0060 (12)
O2B	0.0822 (14)	0.0658 (15)	0.0800 (13)	−0.0033 (13)	0.0051 (13)	0.0127 (13)
C7B	0.0488 (14)	0.0476 (16)	0.0541 (16)	−0.0071 (13)	0.0227 (12)	−0.0038 (14)
C9B	0.0545 (16)	0.0520 (17)	0.0523 (16)	0.0047 (15)	0.0148 (13)	0.0004 (14)
C6B	0.0728 (19)	0.0565 (18)	0.0504 (17)	0.0013 (17)	0.0224 (15)	0.0047 (15)
C8B	0.0555 (16)	0.0487 (16)	0.0566 (16)	0.0090 (15)	0.0178 (13)	0.0005 (14)
C2B	0.0716 (19)	0.0511 (19)	0.0646 (18)	−0.0018 (16)	0.0379 (15)	−0.0023 (16)
C5B	0.0644 (17)	0.0455 (17)	0.0676 (19)	0.0141 (15)	0.0231 (15)	0.0061 (15)
C10B	0.0675 (19)	0.064 (2)	0.0547 (16)	−0.0061 (17)	0.0259 (14)	−0.0025 (17)
C11B	0.075 (2)	0.066 (2)	0.0639 (19)	−0.0088 (18)	0.0247 (16)	−0.0154 (17)
C1B	0.0708 (18)	0.0455 (17)	0.0530 (16)	0.0069 (15)	0.0296 (15)	−0.0022 (14)
C12B	0.137 (4)	0.098 (4)	0.086 (3)	−0.047 (3)	0.043 (3)	−0.009 (3)
C3B	0.079 (2)	0.080 (3)	0.111 (3)	−0.006 (2)	0.058 (2)	−0.028 (3)
C13B	0.134 (4)	0.093 (3)	0.077 (3)	−0.022 (4)	0.030 (3)	−0.030 (3)
C1A	0.0580 (18)	0.059 (2)	0.0647 (18)	0.0051 (16)	0.0210 (16)	−0.0113 (18)
C2A	0.0517 (17)	0.069 (2)	0.084 (2)	0.0060 (17)	0.0268 (16)	−0.0115 (19)
C3A	0.096 (3)	0.105 (3)	0.085 (3)	−0.027 (3)	0.053 (2)	−0.014 (3)
C4A	0.0421 (14)	0.059 (2)	0.0702 (19)	−0.0021 (14)	0.0149 (13)	−0.0007 (16)
C5A	0.076 (2)	0.059 (2)	0.087 (3)	0.014 (2)	0.0197 (19)	−0.003 (2)
C6A	0.089 (2)	0.069 (2)	0.064 (2)	0.002 (2)	0.0107 (18)	0.006 (2)
C7A	0.0706 (19)	0.063 (2)	0.069 (2)	−0.0111 (17)	0.0302 (16)	−0.0028 (18)
C8A	0.0582 (18)	0.068 (2)	0.073 (2)	0.0080 (18)	0.0184 (16)	−0.0084 (19)
C9A	0.0570 (17)	0.065 (2)	0.0634 (19)	0.0084 (17)	0.0098 (15)	−0.0041 (18)
C10A	0.089 (3)	0.093 (3)	0.071 (2)	−0.017 (2)	0.038 (2)	−0.006 (2)
C11A	0.073 (2)	0.086 (3)	0.0644 (19)	0.000 (2)	0.0234 (16)	−0.007 (2)
C13A	0.106 (3)	0.084 (3)	0.084 (3)	−0.013 (3)	0.036 (3)	−0.003 (2)
C12A	0.105 (3)	0.126 (4)	0.073 (2)	−0.010 (3)	0.030 (2)	−0.022 (3)

Geometric parameters (Å, º) top

C4B—C9B	1.382 (4)	C13B—H136	0.95 (5)
C4B—C5B	1.385 (4)	C13B—H134	0.86 (4)
C4B—C2B	1.517 (4)	C13B—H135	1.10 (7)
O2A—C1A	1.219 (3)	C1A—C2A	1.496 (5)
O1A—C1A	1.303 (4)	C2A—C4A	1.519 (4)
O1A—H1AO	0.94 (6)	C2A—C3A	1.536 (6)
O1B—C1B	1.301 (4)	C2A—H2A	0.89 (4)
O1B—H1BO	1.07 (5)	C3A—H3A3	1.05 (4)
O2B—C1B	1.226 (3)	C3A—H3A2	0.87 (4)
C7B—C8B	1.383 (4)	C3A—H3A1	1.03 (5)
C7B—C6B	1.386 (4)	C4A—C9A	1.377 (4)
C7B—C10B	1.495 (4)	C4A—C5A	1.384 (4)
C9B—C8B	1.382 (4)	C5A—C6A	1.385 (5)
C9B—H9B	0.96 (3)	C5A—H5A	0.85 (3)
C6B—C5B	1.378 (4)	C6A—C7A	1.376 (5)
C6B—H6B	1.03 (3)	C6A—H6A	1.00 (4)
C8B—H8B	0.93 (4)	C7A—C8A	1.375 (4)
C2B—C1B	1.517 (4)	C7A—C10A	1.515 (5)
C2B—C3B	1.521 (5)	C8A—C9A	1.374 (4)
C2B—H2B	1.01 (3)	C8A—H8A	1.01 (4)
C5B—H5B	0.99 (3)	C9A—H9A	0.93 (3)
C10B—C11B	1.529 (4)	C10A—C11A	1.516 (6)
C10B—H103	1.00 (3)	C10A—H101	0.96 (4)
C10B—H104	1.01 (3)	C10A—H102	0.97 (5)
C11B—C12B	1.508 (6)	C11A—C13A	1.506 (6)
C11B—C13B	1.526 (5)	C11A—C12A	1.520 (5)
C11B—H11B	1.08 (3)	C11A—H11A	0.95 (4)
C12B—H126	1.12 (8)	C13A—H123	1.03 (6)
C12B—H125	0.98 (4)	C13A—H121	1.04 (4)
C12B—H124	1.05 (6)	C13A—H122	1.06 (5)
C3B—H3B3	1.14 (5)	C12A—H133	1.10 (6)
C3B—H3B2	1.00 (3)	C12A—H132	0.99 (6)
C3B—H3B1	1.00 (6)	C12A—H131	1.12 (5)

C9B—C4B—C5B	117.1 (3)	H134—C13B—H135	112 (4)
C9B—C4B—C2B	120.0 (3)	O2A—C1A—O1A	121.9 (3)
C5B—C4B—C2B	122.8 (3)	O2A—C1A—C2A	122.6 (3)
C1A—O1A—H1AO	108 (4)	O1A—C1A—C2A	115.5 (3)
C1B—O1B—H1BO	105 (2)	C1A—C2A—C4A	108.3 (3)
C8B—C7B—C6B	116.9 (3)	C1A—C2A—C3A	111.3 (3)
C8B—C7B—C10B	122.8 (3)	C4A—C2A—C3A	113.5 (3)
C6B—C7B—C10B	120.3 (3)	C1A—C2A—H2A	105 (3)
C8B—C9B—C4B	121.4 (3)	C4A—C2A—H2A	108 (2)
C8B—C9B—H9B	120 (2)	C3A—C2A—H2A	110 (2)
C4B—C9B—H9B	118 (2)	C2A—C3A—H3A3	109 (2)
C5B—C6B—C7B	121.7 (3)	C2A—C3A—H3A2	112 (3)
C5B—C6B—H6B	119.4 (19)	H3A3—C3A—H3A2	107 (3)
C7B—C6B—H6B	119.0 (19)	C2A—C3A—H3A1	114 (2)
C9B—C8B—C7B	121.5 (3)	H3A3—C3A—H3A1	113 (4)
C9B—C8B—H8B	119.7 (18)	H3A2—C3A—H3A1	103 (3)
C7B—C8B—H8B	118.7 (17)	C9A—C4A—C5A	116.9 (3)
C4B—C2B—C1B	107.7 (2)	C9A—C4A—C2A	122.6 (3)
C4B—C2B—C3B	114.4 (3)	C5A—C4A—C2A	120.4 (3)
C1B—C2B—C3B	111.4 (3)	C4A—C5A—C6A	120.9 (4)
C4B—C2B—H2B	108.2 (16)	C4A—C5A—H5A	113 (2)
C1B—C2B—H2B	104.6 (16)	C6A—C5A—H5A	126 (2)
C3B—C2B—H2B	110.0 (15)	C7A—C6A—C5A	121.7 (4)
C6B—C5B—C4B	121.3 (3)	C7A—C6A—H6A	119 (2)
C6B—C5B—H5B	116.7 (16)	C5A—C6A—H6A	119 (2)
C4B—C5B—H5B	121.8 (16)	C8A—C7A—C6A	117.1 (3)
C7B—C10B—C11B	113.9 (3)	C8A—C7A—C10A	122.2 (3)
C7B—C10B—H103	106.8 (17)	C6A—C7A—C10A	120.7 (4)
C11B—C10B—H103	107.5 (16)	C9A—C8A—C7A	121.4 (3)
C7B—C10B—H104	107.4 (16)	C9A—C8A—H8A	118.3 (17)
C11B—C10B—H104	109.0 (18)	C7A—C8A—H8A	120.2 (17)
H103—C10B—H104	112 (2)	C8A—C9A—C4A	121.9 (3)
C12B—C11B—C13B	110.9 (4)	C8A—C9A—H9A	120.0 (18)
C12B—C11B—C10B	111.8 (3)	C4A—C9A—H9A	118.0 (18)
C13B—C11B—C10B	110.0 (4)	C7A—C10A—C11A	114.2 (3)
C12B—C11B—H11B	98.8 (16)	C7A—C10A—H101	112 (2)
C13B—C11B—H11B	112.7 (14)	C11A—C10A—H101	106 (2)
C10B—C11B—H11B	112.2 (17)	C7A—C10A—H102	109 (3)
O2B—C1B—O1B	122.4 (3)	C11A—C10A—H102	105 (3)
O2B—C1B—C2B	122.2 (3)	H101—C10A—H102	111 (3)
O1B—C1B—C2B	115.3 (3)	C13A—C11A—C10A	111.5 (4)
C11B—C12B—H126	100 (4)	C13A—C11A—C12A	110.0 (4)
C11B—C12B—H125	117 (3)	C10A—C11A—C12A	111.7 (4)
H126—C12B—H125	110 (4)	C13A—C11A—H11A	117 (3)
C11B—C12B—H124	106 (3)	C10A—C11A—H11A	107 (3)
H126—C12B—H124	109 (5)	C12A—C11A—H11A	99 (2)
H125—C12B—H124	113 (4)	C11A—C13A—H123	112 (4)
C2B—C3B—H3B3	116 (2)	C11A—C13A—H121	110 (3)
C2B—C3B—H3B2	105.4 (17)	H123—C13A—H121	102 (4)
H3B3—C3B—H3B2	109 (3)	C11A—C13A—H122	105 (2)
C2B—C3B—H3B1	108 (3)	H123—C13A—H122	115 (5)
H3B3—C3B—H3B1	109 (4)	H121—C13A—H122	114 (3)
H3B2—C3B—H3B1	109 (3)	C11A—C12A—H133	110 (3)
C11B—C13B—H136	98 (3)	C11A—C12A—H132	104 (3)
C11B—C13B—H134	109 (3)	H133—C12A—H132	111 (4)
H136—C13B—H134	106 (4)	C11A—C12A—H131	106 (2)
C11B—C13B—H135	114 (3)	H133—C12A—H131	113 (4)
H136—C13B—H135	117 (4)	H132—C12A—H131	112 (4)

C5B—C4B—C9B—C8B	−1.1 (4)	O2A—C1A—C2A—C4A	95.9 (4)
C2B—C4B—C9B—C8B	179.3 (3)	O1A—C1A—C2A—C4A	−81.7 (4)
C8B—C7B—C6B—C5B	−1.4 (4)	O2A—C1A—C2A—C3A	−29.6 (5)
C10B—C7B—C6B—C5B	177.7 (3)	O1A—C1A—C2A—C3A	152.8 (3)
C4B—C9B—C8B—C7B	−0.5 (4)	C1A—C2A—C4A—C9A	−85.5 (4)
C6B—C7B—C8B—C9B	1.7 (4)	C3A—C2A—C4A—C9A	38.7 (4)
C10B—C7B—C8B—C9B	−177.3 (3)	C1A—C2A—C4A—C5A	91.4 (4)
C9B—C4B—C2B—C1B	84.3 (3)	C3A—C2A—C4A—C5A	−144.4 (4)
C5B—C4B—C2B—C1B	−95.3 (3)	C9A—C4A—C5A—C6A	−1.2 (5)
C9B—C4B—C2B—C3B	−151.3 (3)	C2A—C4A—C5A—C6A	−178.3 (3)
C5B—C4B—C2B—C3B	29.1 (4)	C4A—C5A—C6A—C7A	0.5 (6)
C7B—C6B—C5B—C4B	−0.2 (5)	C5A—C6A—C7A—C8A	0.4 (5)
C9B—C4B—C5B—C6B	1.4 (4)	C5A—C6A—C7A—C10A	−177.0 (3)
C2B—C4B—C5B—C6B	−178.9 (3)	C6A—C7A—C8A—C9A	−0.5 (5)
C8B—C7B—C10B—C11B	101.8 (3)	C10A—C7A—C8A—C9A	176.8 (3)
C6B—C7B—C10B—C11B	−77.2 (4)	C7A—C8A—C9A—C4A	−0.2 (5)
C7B—C10B—C11B—C12B	−68.0 (5)	C5A—C4A—C9A—C8A	1.1 (5)
C7B—C10B—C11B—C13B	168.3 (4)	C2A—C4A—C9A—C8A	178.1 (3)
C4B—C2B—C1B—O2B	−94.6 (3)	C8A—C7A—C10A—C11A	−93.2 (5)
C3B—C2B—C1B—O2B	139.2 (3)	C6A—C7A—C10A—C11A	84.0 (5)
C4B—C2B—C1B—O1B	83.5 (3)	C7A—C10A—C11A—C13A	67.9 (5)
C3B—C2B—C1B—O1B	−42.7 (4)	C7A—C10A—C11A—C12A	−168.7 (4)

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Volume 62| Part 7| July 2006| Pages e17-e18

https://doi.org/10.1107/S1600536806020575

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addenda and errata\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Redetermination and H-atom refinement of (S)-(+)-ibuprofen. Corrigendum.

1. Comment

2. Experimental

Supporting information

References

addenda and errata