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Hydrolysis of the methyl ester (±)-threo-methyl phenidate afforded the free acid in 40% yield, viz. (±)-threo-ritalinic acid, C13H17NO2. Hydrolysis and subsequent crystallization were accomplished at pH values between 5 and 7 to yield colourless prisms which were analysed by X-ray crystallography. Crystals of (±)-threo-ritalinic acid belong to the P21/n space group and form inter­molecular hydrogen bonds. An anti­periplanar disposition of the H atoms of the (HOOC-)CH-CHpy group (py is pyridine) was found in both the solid (diffraction analysis) and solution state (NMR analysis). It was also determined that (±)-threo-ritalinic acid conforms to the minimization of negative gauche+-gauche- inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827011302595X/fm3004sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827011302595X/fm3004Isup2.hkl
Contains datablock I

txt

Text file https://doi.org/10.1107/S010827011302595X/fm3004Isup3.txt
Supplementary material

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S010827011302595X/fm3004sup4.pdf
Supplementary material

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827011302595X/fm3004sup5.cif
Contains datablock x231012_0ma

CCDC reference: 936328

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: OLEX2 (Dolomanov et al., 2009) and SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and ORTEPIII (Johnson & Burnett, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(R,R)-2-Phenyl-2-(piperidin-2-yl)acetic acid top
Crystal data top
C13H17NO2F(000) = 472
Mr = 219.28Dx = 1.292 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 895 reflections
a = 13.495 (3) Åθ = 3.2–24.3°
b = 5.6335 (12) ŵ = 0.09 mm1
c = 15.721 (4) ÅT = 100 K
β = 109.368 (8)°Rod, colourless
V = 1127.5 (4) Å30.14 × 0.05 × 0.02 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer
2603 independent reflections
Radiation source: fine-focus sealed tube1482 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.097
φ and ω scansθmax = 27.6°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2006)
h = 1717
Tmin = 0.988, Tmax = 0.998k = 76
10280 measured reflectionsl = 2020
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.065Hydrogen site location: difference Fourier map
wR(F2) = 0.143All H-atom parameters refined
S = 1.12 w = 1/[σ2(Fo2) + (0.0513P)2]
where P = (Fo2 + 2Fc2)/3
2603 reflections(Δ/σ)max = 0.007
213 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.28 e Å3
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
xyzUiso*/Ueq
O11.10921 (14)0.2562 (3)0.61033 (13)0.0188 (5)
O20.99451 (14)0.0390 (3)0.59486 (12)0.0173 (5)
N10.84435 (17)0.3000 (4)0.42549 (15)0.0149 (5)
H1A0.867 (2)0.458 (6)0.418 (2)0.037 (9)*
H1B0.903 (3)0.195 (6)0.423 (2)0.049 (10)*
C20.8278 (2)0.2914 (5)0.51527 (18)0.0162 (6)
H20.803 (2)0.131 (5)0.5193 (18)0.017 (7)*
C30.7376 (2)0.4585 (6)0.5116 (2)0.0238 (7)
H3A0.725 (2)0.446 (5)0.573 (2)0.031 (8)*
H3B0.759 (2)0.623 (6)0.507 (2)0.025 (8)*
C40.6384 (2)0.3989 (6)0.4352 (2)0.0265 (7)
H4A0.615 (2)0.235 (6)0.449 (2)0.035 (9)*
H4B0.579 (2)0.509 (5)0.4344 (19)0.030 (8)*
C50.6590 (2)0.4042 (6)0.34566 (19)0.0214 (7)
H5A0.599 (2)0.345 (5)0.300 (2)0.021 (8)*
H5B0.676 (2)0.569 (5)0.3305 (19)0.024 (8)*
C60.7487 (2)0.2388 (5)0.3486 (2)0.0197 (6)
H6A0.766 (2)0.254 (5)0.295 (2)0.021 (8)*
H6B0.731 (2)0.075 (5)0.3593 (19)0.024 (8)*
C70.9294 (2)0.3550 (5)0.58976 (18)0.0160 (6)
H70.948 (2)0.514 (5)0.5718 (18)0.017 (7)*
C80.9128 (2)0.3658 (4)0.68055 (18)0.0147 (6)
C90.8648 (2)0.1789 (5)0.71042 (19)0.0187 (6)
H90.837 (2)0.043 (5)0.6660 (18)0.019 (7)*
C100.8501 (2)0.1864 (5)0.7927 (2)0.0202 (6)
H100.814 (2)0.046 (6)0.814 (2)0.038 (9)*
C110.8852 (2)0.3802 (5)0.8488 (2)0.0222 (7)
H110.877 (2)0.380 (5)0.907 (2)0.038 (9)*
C120.9339 (2)0.5657 (5)0.82067 (19)0.0228 (7)
H120.958 (2)0.705 (5)0.858 (2)0.023 (8)*
C130.9474 (2)0.5600 (5)0.73721 (19)0.0189 (6)
H130.977 (2)0.698 (5)0.712 (2)0.036 (9)*
C141.0181 (2)0.1778 (5)0.59797 (17)0.0144 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0162 (10)0.0149 (10)0.0247 (11)0.0001 (8)0.0061 (8)0.0016 (8)
O20.0217 (10)0.0107 (9)0.0200 (11)0.0004 (8)0.0076 (8)0.0008 (8)
N10.0172 (12)0.0129 (12)0.0143 (12)0.0006 (10)0.0050 (10)0.0001 (9)
C20.0154 (14)0.0159 (14)0.0182 (15)0.0004 (12)0.0067 (12)0.0027 (11)
C30.0189 (16)0.0322 (18)0.0205 (17)0.0060 (14)0.0068 (13)0.0013 (14)
C40.0204 (17)0.036 (2)0.0229 (17)0.0062 (15)0.0062 (13)0.0031 (14)
C50.0198 (16)0.0242 (17)0.0154 (15)0.0022 (13)0.0007 (13)0.0010 (12)
C60.0222 (16)0.0194 (16)0.0148 (15)0.0038 (13)0.0024 (12)0.0057 (12)
C70.0186 (14)0.0115 (14)0.0193 (15)0.0013 (12)0.0083 (12)0.0002 (11)
C80.0124 (13)0.0139 (14)0.0155 (14)0.0024 (11)0.0016 (11)0.0014 (11)
C90.0200 (15)0.0180 (15)0.0177 (15)0.0010 (12)0.0057 (12)0.0008 (12)
C100.0186 (15)0.0230 (15)0.0193 (16)0.0016 (13)0.0068 (12)0.0050 (13)
C110.0256 (16)0.0267 (17)0.0146 (15)0.0067 (13)0.0071 (13)0.0043 (13)
C120.0271 (17)0.0225 (16)0.0165 (15)0.0013 (14)0.0044 (13)0.0044 (13)
C130.0194 (15)0.0155 (14)0.0203 (15)0.0040 (12)0.0044 (12)0.0023 (12)
C140.0199 (15)0.0130 (14)0.0120 (14)0.0015 (11)0.0075 (12)0.0003 (11)
Geometric parameters (Å, º) top
O1—C141.260 (3)C5—C61.517 (4)
O2—C141.259 (3)C6—H6A0.95 (3)
N1—H1A0.96 (3)C6—H6B0.98 (3)
N1—H1B1.00 (4)C7—H70.99 (3)
N1—C21.501 (3)C7—C81.518 (4)
N1—C61.487 (3)C7—C141.530 (4)
C2—H20.97 (3)C8—C91.397 (4)
C2—C31.524 (4)C8—C131.390 (4)
C2—C71.522 (4)C9—H91.02 (3)
C3—H3A1.04 (3)C9—C101.373 (4)
C3—H3B0.98 (3)C10—H101.04 (3)
C3—C41.511 (4)C10—C111.385 (4)
C4—H4A1.02 (3)C11—H110.95 (3)
C4—H4B1.01 (3)C11—C121.382 (4)
C4—C51.522 (4)C12—H120.97 (3)
C5—H5A0.95 (3)C12—C131.384 (4)
C5—H5B1.00 (3)C13—H131.01 (3)
H1A—N1—H1B105 (3)N1—C6—H6B105.9 (16)
C2—N1—H1A107.4 (19)C5—C6—H6A110.3 (16)
C2—N1—H1B113 (2)C5—C6—H6B110.3 (16)
C6—N1—H1A109.6 (19)H6A—C6—H6B113 (2)
C6—N1—H1B108 (2)C2—C7—H7103.7 (16)
C6—N1—C2113.4 (2)C2—C7—C14113.1 (2)
N1—C2—H2104.6 (16)C8—C7—C2110.9 (2)
N1—C2—C3108.1 (2)C8—C7—H7111.0 (15)
N1—C2—C7109.8 (2)C8—C7—C14107.6 (2)
C3—C2—H2106.8 (16)C14—C7—H7110.7 (15)
C7—C2—H2114.2 (16)C9—C8—C7121.0 (2)
C7—C2—C3112.9 (2)C13—C8—C7120.8 (2)
C2—C3—H3A107.3 (16)C13—C8—C9118.2 (3)
C2—C3—H3B109.3 (17)C8—C9—H9116.1 (15)
H3A—C3—H3B106 (2)C10—C9—C8121.4 (3)
C4—C3—C2112.2 (3)C10—C9—H9122.3 (15)
C4—C3—H3A110.6 (16)C9—C10—H10120.5 (18)
C4—C3—H3B110.8 (18)C9—C10—C11119.9 (3)
C3—C4—H4A106.6 (18)C11—C10—H10119.6 (17)
C3—C4—H4B111.3 (17)C10—C11—H11119.0 (19)
C3—C4—C5110.2 (3)C12—C11—C10119.4 (3)
H4A—C4—H4B105 (2)C12—C11—H11121.6 (19)
C5—C4—H4A112.1 (17)C11—C12—H12121.0 (16)
C5—C4—H4B111.3 (17)C11—C12—C13120.8 (3)
C4—C5—H5A108.8 (17)C13—C12—H12118.2 (17)
C4—C5—H5B111.4 (16)C8—C13—H13116.6 (17)
H5A—C5—H5B110 (2)C12—C13—C8120.3 (3)
C6—C5—C4110.4 (3)C12—C13—H13123.0 (17)
C6—C5—H5A106.3 (16)O1—C14—O2124.6 (2)
C6—C5—H5B109.4 (16)O1—C14—C7118.7 (2)
N1—C6—C5110.6 (2)O2—C14—C7116.7 (2)
N1—C6—H6A107.1 (17)
N1—C2—C3—C456.2 (3)C6—N1—C2—C7179.7 (2)
N1—C2—C7—C8175.7 (2)C7—C2—C3—C4177.8 (3)
N1—C2—C7—C1463.3 (3)C7—C8—C9—C10179.6 (3)
C2—N1—C6—C557.8 (3)C7—C8—C13—C12178.6 (3)
C2—C3—C4—C557.1 (4)C8—C7—C14—O199.4 (3)
C2—C7—C8—C951.1 (3)C8—C7—C14—O278.2 (3)
C2—C7—C8—C13130.5 (3)C8—C9—C10—C111.4 (4)
C2—C7—C14—O1137.8 (2)C9—C8—C13—C120.1 (4)
C2—C7—C14—O244.6 (3)C9—C10—C11—C120.7 (4)
C3—C2—C7—C855.1 (3)C10—C11—C12—C130.3 (4)
C3—C2—C7—C14176.0 (2)C11—C12—C13—C80.5 (4)
C3—C4—C5—C655.6 (4)C13—C8—C9—C101.1 (4)
C4—C5—C6—N155.7 (4)C14—C7—C8—C973.0 (3)
C6—N1—C2—C356.8 (3)C14—C7—C8—C13105.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.96 (3)1.73 (3)2.682 (3)172 (2)
N1—H1B···O2ii1.00 (4)1.74 (3)2.730 (3)171 (3)
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+2, y, z+1.
 

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