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The title compound (3-carboxy­piperidinium chloride), C6H12NO2+·Cl, is the hydro­chloride of nipecotic acid and is used as a drug inter­mediate and in the synthesis of γ-amino­butyric acid (GABA) uptake inhibitors. The geometric parameters are in the normal ranges. The crystal packing is stabilized by O—H...Cl and N—H...Cl hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805005337/nc6023sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805005337/nc6023Isup2.hkl
Contains datablock I

CCDC reference: 269823

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.022
  • wR factor = 0.057
  • Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry ..... 80 PerFit
Alert level C PLAT213_ALERT_2_C Atom O2 has ADP max/min Ratio ............. 3.80 prolat PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.14 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 3.17 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 Cl
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 25.48 From the CIF: _reflns_number_total 1477 Count of symmetry unique reflns 816 Completeness (_total/calc) 181.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 661 Fraction of Friedel pairs measured 0.810 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 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 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PLATON.

3-carboxypiperidinium chloride top
Crystal data top
C6H12NO2+·ClF(000) = 176
Mr = 165.62Dx = 1.364 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 8363 reflections
a = 7.2545 (10) Åθ = 3.8–25.7°
b = 7.2018 (9) ŵ = 0.42 mm1
c = 7.7886 (13) ÅT = 173 K
β = 97.819 (12)°Block, colourless
V = 403.14 (10) Å30.37 × 0.23 × 0.19 mm
Z = 2
Data collection top
Stoe IPDS-II two-circle
diffractometer
1477 independent reflections
Radiation source: fine-focus sealed tube1460 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
ω scansθmax = 25.5°, θmin = 3.9°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
h = 88
Tmin = 0.861, Tmax = 0.925k = 88
3354 measured reflectionsl = 99
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.022 w = 1/[σ2(Fo2) + (0.0315P)2 + 0.0946P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.057(Δ/σ)max < 0.001
S = 1.10Δρmax = 0.20 e Å3
1477 reflectionsΔρmin = 0.17 e Å3
104 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.075 (10)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 671 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.10 (6)
Special details top

Experimental. ;

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
Cl10.19824 (4)0.89548 (5)0.87208 (4)0.01996 (13)
C10.2393 (2)0.8196 (2)0.41007 (19)0.0182 (3)
H10.26630.68380.40370.022*
C20.11341 (19)0.8717 (3)0.24271 (17)0.0193 (3)
H2A0.00400.80020.23400.023*
H2B0.08251.00550.24410.023*
N30.21165 (19)0.82958 (19)0.09018 (17)0.0187 (3)
H3A0.225 (3)0.696 (3)0.091 (3)0.034 (6)*
H3B0.131 (3)0.863 (3)0.002 (3)0.030 (5)*
C40.3972 (2)0.9239 (2)0.0966 (2)0.0236 (4)
H4A0.37901.06000.08880.028*
H4B0.45780.88380.00370.028*
C50.5219 (2)0.8764 (3)0.26385 (19)0.0246 (3)
H5A0.63950.94730.26960.029*
H5B0.55280.74250.26450.029*
C60.4268 (2)0.9222 (2)0.42292 (19)0.0216 (4)
H6A0.40611.05780.42890.026*
H6B0.50770.88380.52970.026*
C70.1465 (2)0.8503 (2)0.5709 (2)0.0246 (4)
O10.03690 (16)0.8621 (2)0.53883 (15)0.0353 (4)
H1O0.074 (4)0.872 (5)0.642 (3)0.069 (8)*
O20.2290 (2)0.8526 (5)0.71339 (17)0.0714 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.01918 (18)0.02398 (19)0.01762 (17)0.00124 (17)0.00571 (11)0.00071 (17)
C10.0171 (7)0.0238 (7)0.0137 (7)0.0006 (6)0.0019 (6)0.0003 (6)
C20.0170 (6)0.0289 (10)0.0124 (6)0.0022 (7)0.0034 (5)0.0001 (7)
N30.0199 (6)0.0248 (7)0.0116 (6)0.0021 (5)0.0028 (5)0.0003 (5)
C40.0230 (7)0.0296 (11)0.0197 (7)0.0015 (7)0.0083 (6)0.0038 (7)
C50.0167 (6)0.0341 (9)0.0235 (7)0.0028 (8)0.0048 (5)0.0018 (8)
C60.0208 (7)0.0258 (10)0.0175 (6)0.0033 (7)0.0001 (5)0.0034 (6)
C70.0229 (8)0.0354 (12)0.0159 (7)0.0005 (6)0.0035 (6)0.0001 (6)
O10.0221 (6)0.0668 (11)0.0179 (5)0.0079 (6)0.0064 (4)0.0031 (7)
O20.0276 (6)0.174 (3)0.0125 (5)0.0070 (11)0.0020 (5)0.0038 (10)
Geometric parameters (Å, º) top
C1—C71.516 (2)C4—H4A0.9900
C1—C21.5329 (19)C4—H4B0.9900
C1—C61.539 (2)C5—C61.534 (2)
C1—H11.0000C5—H5A0.9900
C2—N31.4972 (18)C5—H5B0.9900
C2—H2A0.9900C6—H6A0.9900
C2—H2B0.9900C6—H6B0.9900
N3—C41.502 (2)C7—O21.187 (2)
N3—H3A0.96 (2)C7—O11.323 (2)
N3—H3B0.90 (2)O1—H1O0.89 (3)
C4—C51.521 (2)
C7—C1—C2112.75 (13)C5—C4—H4A109.5
C7—C1—C6111.35 (12)N3—C4—H4B109.5
C2—C1—C6110.91 (13)C5—C4—H4B109.5
C7—C1—H1107.2H4A—C4—H4B108.1
C2—C1—H1107.2C4—C5—C6111.29 (13)
C6—C1—H1107.2C4—C5—H5A109.4
N3—C2—C1109.41 (12)C6—C5—H5A109.4
N3—C2—H2A109.8C4—C5—H5B109.4
C1—C2—H2A109.8C6—C5—H5B109.4
N3—C2—H2B109.8H5A—C5—H5B108.0
C1—C2—H2B109.8C5—C6—C1109.56 (12)
H2A—C2—H2B108.2C5—C6—H6A109.8
C2—N3—C4113.78 (12)C1—C6—H6A109.8
C2—N3—H3A104.8 (14)C5—C6—H6B109.8
C4—N3—H3A111.3 (14)C1—C6—H6B109.8
C2—N3—H3B104.6 (12)H6A—C6—H6B108.2
C4—N3—H3B113.1 (13)O2—C7—O1122.79 (15)
H3A—N3—H3B108.7 (19)O2—C7—C1123.39 (16)
N3—C4—C5110.65 (13)O1—C7—C1113.68 (14)
N3—C4—H4A109.5C7—O1—H1O104.9 (18)
C7—C1—C2—N3177.50 (13)C7—C1—C6—C5176.03 (15)
C6—C1—C2—N356.85 (18)C2—C1—C6—C557.54 (18)
C1—C2—N3—C456.29 (19)C2—C1—C7—O2165.3 (2)
C2—N3—C4—C555.54 (19)C6—C1—C7—O239.9 (3)
N3—C4—C5—C654.7 (2)C2—C1—C7—O118.9 (2)
C4—C5—C6—C156.3 (2)C6—C1—C7—O1144.29 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···Cl10.89 (3)2.11 (3)2.9985 (13)173 (2)
N3—H3A···Cl1i0.96 (2)2.20 (2)3.1428 (15)166 (2)
N3—H3B···Cl1ii0.90 (2)2.47 (2)3.2525 (15)146.8 (16)
N3—H3B···O2ii0.90 (2)2.419 (19)2.9590 (19)119.0 (15)
Symmetry codes: (i) x, y1/2, z+1; (ii) x, y, z1.
 

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