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The structure of the title compound, C6H12NO2+·Cl, consists of an isonipecotate cation and a Cl anion linked by inter­molecular O—H...Cl and N—H...Cl inter­actions into a three-dimensional network structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806007252/hk6075sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806007252/hk6075Isup2.hkl
Contains datablock I

CCDC reference: 605093

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.046
  • wR factor = 0.123
  • Data-to-parameter ratio = 15.5

checkCIF/PLATON results

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Alert level C STRVA01_ALERT_4_C Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.400 From the CIF: _refine_ls_abs_structure_Flack_su 0.130 PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero ....... 0.40 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.40 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C6 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.27 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
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 25.08 From the CIF: _reflns_number_total 1426 Count of symmetry unique reflns 860 Completeness (_total/calc) 165.81% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 566 Fraction of Friedel pairs measured 0.658 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 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: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Johnson & Burnett, 1996); software used to prepare material for publication: SHELXTL (Bruker, 2002).

Isonipecotate chloride top
Crystal data top
C6H12NO2+·ClF(000) = 352
Mr = 165.62Dx = 1.365 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 352 reflections
a = 7.0405 (7) Åθ = 2.7–25.1°
b = 7.4902 (7) ŵ = 0.42 mm1
c = 15.2806 (15) ÅT = 298 K
V = 805.82 (14) Å3Block, colourless
Z = 40.36 × 0.31 × 0.18 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1426 independent reflections
Radiation source: fine-focus sealed tube1394 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
ω scansθmax = 25.1°, θmin = 2.7°
Absorption correction: numerical
(SADABS; Sheldrick, 1996)
h = 68
Tmin = 0.86, Tmax = 0.93k = 88
3980 measured reflectionsl = 1818
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)] = 0.046H-atom parameters constrained
wR(F2) = 0.123 w = 1/[σ2(Fo2) + (0.0636P)2 + 0.4526P]
where P = (Fo2 + 2Fc2)/3
S = 1.20(Δ/σ)max < 0.001
1426 reflectionsΔρmax = 0.76 e Å3
92 parametersΔρmin = 0.22 e Å3
0 restraintsAbsolute structure: Flack (1983), with 568 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.40 (13)
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
Cl10.19967 (11)0.45733 (11)0.92845 (5)0.0365 (2)
O10.4268 (4)0.4291 (6)0.76164 (17)0.0674 (10)
H10.37220.44600.80830.101*
N10.9303 (4)0.5567 (4)0.54806 (18)0.0394 (7)
H1A1.00820.54930.50150.047*
H1B0.89220.67100.55300.047*
C20.6281 (5)0.4490 (6)0.6107 (2)0.0403 (8)
H2A0.52350.36680.60170.048*
H2B0.57600.56850.61550.048*
C10.7613 (5)0.4404 (5)0.5333 (2)0.0434 (8)
H1C0.80240.31810.52450.052*
H1D0.69500.47900.48100.052*
C30.7313 (4)0.4012 (4)0.69518 (19)0.0333 (7)
H30.77480.27750.68940.040*
C51.0363 (5)0.5047 (6)0.6282 (2)0.0479 (10)
H5A1.14420.58350.63620.057*
H5B1.08360.38370.62200.057*
C40.9062 (5)0.5162 (6)0.7071 (2)0.0442 (9)
H4A0.97450.47760.75890.053*
H4B0.86790.63930.71590.053*
O20.6659 (4)0.3805 (7)0.84800 (16)0.0873 (13)
C60.6068 (5)0.4097 (5)0.7756 (2)0.0405 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0320 (4)0.0415 (4)0.0361 (4)0.0005 (3)0.0034 (3)0.0003 (3)
O10.0436 (15)0.124 (3)0.0349 (13)0.0116 (18)0.0090 (11)0.0077 (18)
N10.0407 (15)0.0378 (15)0.0396 (15)0.0041 (13)0.0123 (12)0.0030 (13)
C20.0308 (16)0.062 (2)0.0283 (15)0.0035 (18)0.0024 (13)0.0009 (17)
C10.0475 (19)0.056 (2)0.0267 (15)0.0023 (18)0.0018 (14)0.0004 (15)
C30.0357 (17)0.0369 (16)0.0272 (15)0.0003 (13)0.0012 (13)0.0010 (12)
C50.0320 (17)0.061 (3)0.050 (2)0.0018 (16)0.0021 (16)0.0019 (18)
C40.0371 (17)0.059 (2)0.0360 (18)0.0018 (16)0.0041 (14)0.0015 (16)
O20.0485 (17)0.179 (4)0.0347 (15)0.005 (2)0.0024 (13)0.0027 (18)
C60.0376 (18)0.057 (2)0.0271 (16)0.0032 (15)0.0008 (14)0.0019 (15)
Geometric parameters (Å, º) top
O1—C61.293 (4)C1—H1D0.9700
O1—H10.8200C3—C61.511 (4)
N1—C51.486 (5)C3—C41.514 (5)
N1—C11.492 (5)C3—H30.9800
N1—H1A0.9000C5—C41.517 (5)
N1—H1B0.9000C5—H5A0.9700
C2—C11.511 (5)C5—H5B0.9700
C2—C31.524 (4)C4—H4A0.9700
C2—H2A0.9700C4—H4B0.9700
C2—H2B0.9700O2—C61.202 (4)
C1—H1C0.9700
C6—O1—H1109.5C6—C3—C2113.8 (3)
C5—N1—C1111.8 (3)C4—C3—C2110.9 (3)
C5—N1—H1A109.3C6—C3—H3107.1
C1—N1—H1A109.3C4—C3—H3107.1
C5—N1—H1B109.3C2—C3—H3107.1
C1—N1—H1B109.3N1—C5—C4109.7 (3)
H1A—N1—H1B107.9N1—C5—H5A109.7
C1—C2—C3110.9 (3)C4—C5—H5A109.7
C1—C2—H2A109.5N1—C5—H5B109.7
C3—C2—H2A109.5C4—C5—H5B109.7
C1—C2—H2B109.5H5A—C5—H5B108.2
C3—C2—H2B109.5C3—C4—C5111.3 (3)
H2A—C2—H2B108.0C3—C4—H4A109.4
N1—C1—C2110.6 (3)C5—C4—H4A109.4
N1—C1—H1C109.5C3—C4—H4B109.4
C2—C1—H1C109.5C5—C4—H4B109.4
N1—C1—H1D109.5H4A—C4—H4B108.0
C2—C1—H1D109.5O2—C6—O1120.8 (3)
H1C—C1—H1D108.1O2—C6—C3122.7 (3)
C6—C3—C4110.5 (3)O1—C6—C3116.0 (3)
C5—N1—C1—C258.6 (4)C2—C3—C4—C554.8 (4)
C3—C2—C1—N155.4 (4)N1—C5—C4—C356.8 (4)
C1—C2—C3—C6179.2 (3)C4—C3—C6—O252.7 (5)
C1—C2—C3—C453.9 (4)C2—C3—C6—O2178.1 (4)
C1—N1—C5—C458.7 (4)C4—C3—C6—O1135.4 (4)
C6—C3—C4—C5178.1 (3)C2—C3—C6—O19.9 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···Cl1i0.902.263.157 (3)178
N1—H1A···Cl1ii0.902.343.184 (3)156
O1—H1···Cl10.822.203.016 (3)172
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x+3/2, y+1, z1/2.
 

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