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The methoxy­piperidinium cation of the title compound, C6H14NO+·Cl, adopts a chair conformation. The crystal structure is stabilized by N—H...Cl hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807000700/sa2038sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807000700/sa2038Isup2.hkl
Contains datablock I

CCDC reference: 636797

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.030
  • wR factor = 0.079
  • Data-to-parameter ratio = 18.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - C5 .. 6.24 su PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 0.07
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 26.01 From the CIF: _reflns_number_total 1564 Count of symmetry unique reflns 891 Completeness (_total/calc) 175.53% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 673 Fraction of Friedel pairs measured 0.755 Are heavy atom types Z>Si present yes PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

4-methoxypiperidinium chloride top
Crystal data top
C6H14NO+·ClF(000) = 164
Mr = 151.63Dx = 1.200 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 6.6778 (13) ÅCell parameters from 1438 reflections
b = 7.4041 (14) Åθ = 3.1–25.5°
c = 8.6654 (16) ŵ = 0.39 mm1
β = 101.666 (3)°T = 293 K
V = 419.59 (14) Å3Needle, colorless
Z = 20.22 × 0.21 × 0.10 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1564 independent reflections
Radiation source: fine-focus sealed tube1507 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.013
φ and ω scansθmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 78
Tmin = 0.922, Tmax = 0.964k = 99
2344 measured reflectionsl = 107
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.030 w = 1/[σ2(Fo2) + (0.0456P)2 + 0.0315P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.079(Δ/σ)max < 0.001
S = 1.05Δρmax = 0.19 e Å3
1564 reflectionsΔρmin = 0.13 e Å3
84 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.043 (6)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983)
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.00 (7)
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
Cl10.13927 (7)0.44584 (8)0.36920 (5)0.05378 (17)
N10.9025 (3)0.3657 (3)0.63622 (19)0.0536 (4)
H1A0.88430.24530.63040.064*
H1B0.98170.39690.56800.064*
O10.5309 (2)0.3806 (2)0.96713 (17)0.0668 (5)
C11.0076 (3)0.4151 (3)0.7982 (2)0.0571 (6)
H1C1.02990.54450.80490.069*
H1D1.13960.35560.82370.069*
C20.8773 (3)0.3576 (3)0.9145 (2)0.0510 (5)
H2A0.86250.22730.91210.061*
H2B0.94460.39251.02020.061*
C30.6677 (2)0.4448 (6)0.87426 (19)0.0481 (4)
H30.68320.57570.88870.058*
C40.5668 (3)0.4068 (4)0.7053 (2)0.0611 (7)
H4A0.44000.47440.67920.073*
H4B0.53340.27940.69410.073*
C50.7011 (3)0.4567 (5)0.5906 (2)0.0587 (5)
H5A0.63550.42030.48500.070*
H5B0.72030.58660.59080.070*
C60.5849 (4)0.4252 (5)1.1290 (2)0.0699 (7)
H6A0.69960.35331.17840.105*
H6B0.47110.40181.17830.105*
H6C0.62050.55081.14000.105*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0607 (3)0.0562 (3)0.0486 (3)0.0026 (3)0.02092 (17)0.0056 (3)
N10.0676 (11)0.0509 (9)0.0497 (10)0.0071 (8)0.0290 (8)0.0007 (7)
O10.0541 (8)0.0987 (13)0.0519 (8)0.0162 (8)0.0209 (6)0.0129 (8)
C10.0462 (9)0.0715 (18)0.0553 (11)0.0022 (10)0.0143 (7)0.0017 (11)
C20.0538 (11)0.0606 (11)0.0382 (9)0.0005 (9)0.0083 (8)0.0018 (8)
C30.0472 (8)0.0542 (9)0.0456 (9)0.0019 (15)0.0154 (6)0.0044 (11)
C40.0473 (9)0.089 (2)0.0457 (10)0.0044 (11)0.0065 (7)0.0067 (11)
C50.0640 (10)0.0689 (12)0.0430 (9)0.0009 (16)0.0104 (8)0.0086 (13)
C60.0800 (13)0.085 (2)0.0521 (11)0.0081 (16)0.0308 (9)0.0159 (16)
Geometric parameters (Å, º) top
N1—C11.482 (3)C2—H2B0.9700
N1—C51.484 (3)C3—C41.510 (3)
N1—H1A0.9000C3—H30.9800
N1—H1B0.9000C4—C51.513 (3)
O1—C61.415 (3)C4—H4A0.9700
O1—C31.416 (3)C4—H4B0.9700
C1—C21.519 (3)C5—H5A0.9700
C1—H1C0.9700C5—H5B0.9700
C1—H1D0.9700C6—H6A0.9600
C2—C31.517 (3)C6—H6B0.9600
C2—H2A0.9700C6—H6C0.9600
C1—N1—C5111.72 (18)O1—C3—H3108.9
C1—N1—H1A109.3C4—C3—H3108.9
C5—N1—H1A109.3C2—C3—H3108.9
C1—N1—H1B109.3C3—C4—C5112.58 (18)
C5—N1—H1B109.3C3—C4—H4A109.1
H1A—N1—H1B107.9C5—C4—H4A109.1
C6—O1—C3114.86 (17)C3—C4—H4B109.1
N1—C1—C2109.52 (16)C5—C4—H4B109.1
N1—C1—H1C109.8H4A—C4—H4B107.8
C2—C1—H1C109.8N1—C5—C4109.9 (2)
N1—C1—H1D109.8N1—C5—H5A109.7
C2—C1—H1D109.8C4—C5—H5A109.7
H1C—C1—H1D108.2N1—C5—H5B109.7
C3—C2—C1110.74 (18)C4—C5—H5B109.7
C3—C2—H2A109.5H5A—C5—H5B108.2
C1—C2—H2A109.5O1—C6—H6A109.5
C3—C2—H2B109.5O1—C6—H6B109.5
C1—C2—H2B109.5H6A—C6—H6B109.5
H2A—C2—H2B108.1O1—C6—H6C109.5
O1—C3—C4106.02 (19)H6A—C6—H6C109.5
O1—C3—C2113.4 (3)H6B—C6—H6C109.5
C4—C3—C2110.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Cl1i0.902.223.121 (2)176
N1—H1B···Cl1ii0.902.223.112 (2)170
Symmetry codes: (i) x+1, y1/2, z+1; (ii) x+1, y, z.
 

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