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The title compound, also known as salicifoline chloride, C12H20NO2+·Cl, was isolated from Eniconsanthum membranifolium J. Sinclair for X-ray analysis. Salicifoline is hydrogen bonded to a chloride ion via the OH group.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806023361/bt2111sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806023361/bt2111Isup2.hkl
Contains datablock I

CCDC reference: 613599

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C)= 0.003 Å
  • R factor = 0.073
  • wR factor = 0.119
  • Data-to-parameter ratio = 19.3

checkCIF/PLATON results

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No errors found in this datablock

Computing details top

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2001); cell refinement: CrystalClear; data reduction: TEXSAN (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 and TEXSAN.

2-(3-Hydroxy-4-methoxyphenyl)-N,N,N-trimethylethanaminium chloride top
Crystal data top
C12H20NO2+·ClF(000) = 528
Mr = 245.74Dx = 1.272 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybcCell parameters from 2883 reflections
a = 9.758 (5) Åθ = 3.3–27.5°
b = 11.686 (6) ŵ = 0.29 mm1
c = 11.253 (6) ÅT = 296 K
β = 90.180 (7)°Block, colorless
V = 1283.2 (12) Å30.46 × 0.17 × 0.11 mm
Z = 4
Data collection top
Rigaku/MSC Mercury CCD
diffractometer
2928 independent reflections
Graphite monochromator2472 reflections with I > 2σ(I)
Detector resolution: 14.62 pixels mm-1Rint = 0.043
ω scansθmax = 27.5°, θmin = 3.3°
Absorption correction: integration
(NUMABS; Higashi, 1999)
h = 1212
Tmin = 0.919, Tmax = 0.975k = 915
10211 measured reflectionsl = 1214
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)] = 0.073Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.25 w = 1/[σ2(Fo2) + (0.0217P)2 + 0.8281P]
where P = (Fo2 + 2Fc2)/3
2928 reflections(Δ/σ)max < 0.001
152 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.19 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
C10.4264 (2)0.6094 (2)0.3427 (2)0.0356 (6)
C20.5230 (2)0.5401 (2)0.2854 (2)0.0343 (6)
C30.4829 (2)0.4738 (2)0.1893 (2)0.0334 (5)
H10.54670.42650.15270.040*
C40.3486 (2)0.4768 (2)0.14648 (19)0.0299 (5)
C50.2560 (3)0.5468 (2)0.2031 (2)0.0379 (6)
H20.16600.54980.17590.045*
C60.2945 (3)0.6129 (2)0.2998 (2)0.0408 (6)
H30.23030.66010.33600.049*
O10.47340 (19)0.67064 (18)0.43837 (17)0.0532 (6)
C70.3727 (3)0.7201 (3)0.5141 (3)0.0575 (8)
H40.32330.77810.47140.086*
H50.41690.75360.58210.086*
H60.31010.66180.53980.086*
O20.65370 (19)0.5432 (2)0.32778 (19)0.0579 (6)
H70.709 (4)0.498 (3)0.288 (3)0.087*
C80.3036 (3)0.4057 (2)0.04073 (19)0.0359 (6)
H80.25360.45330.01520.043*
H90.38330.37490.00060.043*
C90.2129 (2)0.3087 (2)0.08249 (18)0.0280 (5)
H100.26850.25560.12810.034*
H110.14420.33980.13560.034*
N10.1406 (2)0.24257 (16)0.01491 (16)0.0300 (4)
C100.0428 (3)0.3177 (2)0.0806 (2)0.0476 (7)
H120.09290.37490.12350.071*
H130.01780.35410.02520.071*
H140.00970.27240.13540.071*
C110.0598 (3)0.1496 (2)0.0429 (2)0.0495 (7)
H150.00780.10930.01630.074*
H160.00140.18240.10030.074*
H170.12110.09740.08200.074*
C120.2405 (3)0.1900 (3)0.0982 (2)0.0550 (8)
H180.19260.14230.15400.082*
H190.30500.14450.05410.082*
H200.28850.24920.14010.082*
Cl10.88180 (7)0.40385 (6)0.21980 (6)0.0453 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0302 (13)0.0309 (13)0.0458 (14)0.0040 (11)0.0029 (10)0.0107 (11)
C20.0221 (12)0.0359 (14)0.0449 (14)0.0026 (10)0.0010 (10)0.0086 (11)
C30.0262 (13)0.0322 (13)0.0419 (13)0.0012 (11)0.0037 (10)0.0073 (11)
C40.0297 (13)0.0272 (12)0.0326 (12)0.0056 (10)0.0016 (9)0.0038 (9)
C50.0275 (13)0.0368 (14)0.0493 (15)0.0024 (11)0.0088 (11)0.0023 (12)
C60.0294 (14)0.0329 (15)0.0601 (16)0.0065 (11)0.0043 (12)0.0070 (12)
O10.0350 (11)0.0606 (14)0.0639 (12)0.0037 (9)0.0047 (9)0.0374 (10)
C70.0511 (19)0.060 (2)0.0612 (18)0.0037 (16)0.0154 (15)0.0263 (15)
O20.0249 (10)0.0710 (15)0.0779 (14)0.0054 (10)0.0093 (9)0.0421 (12)
C80.0365 (14)0.0420 (15)0.0292 (12)0.0081 (12)0.0032 (10)0.0032 (11)
C90.0308 (13)0.0316 (13)0.0218 (10)0.0010 (10)0.0040 (9)0.0009 (9)
N10.0326 (11)0.0291 (11)0.0283 (9)0.0002 (9)0.0082 (8)0.0007 (8)
C100.0519 (18)0.0382 (16)0.0526 (16)0.0028 (13)0.0281 (13)0.0054 (13)
C110.0543 (19)0.0372 (15)0.0567 (17)0.0156 (14)0.0153 (13)0.0082 (13)
C120.061 (2)0.064 (2)0.0401 (15)0.0084 (16)0.0006 (13)0.0202 (14)
Cl10.0383 (4)0.0405 (4)0.0570 (4)0.0082 (3)0.0066 (3)0.0027 (3)
Geometric parameters (Å, º) top
C1—O11.370 (3)C8—H80.9700
C1—C61.375 (3)C8—H90.9700
C1—C21.401 (3)C9—N11.513 (3)
C2—O21.361 (3)C9—H100.9700
C2—C31.385 (3)C9—H110.9700
C3—C41.396 (3)N1—C121.487 (3)
C3—H10.9300N1—C101.491 (3)
C4—C51.376 (3)N1—C111.493 (3)
C4—C81.515 (3)C10—H120.9600
C5—C61.385 (4)C10—H130.9600
C5—H20.9300C10—H140.9600
C6—H30.9300C11—H150.9600
O1—C71.425 (3)C11—H160.9600
C7—H40.9600C11—H170.9600
C7—H50.9600C12—H180.9600
C7—H60.9600C12—H190.9600
O2—H70.88 (4)C12—H200.9600
C8—C91.514 (3)
O1—C1—C6124.8 (2)H8—C8—H9108.2
O1—C1—C2116.1 (2)N1—C9—C8115.40 (17)
C6—C1—C2119.1 (2)N1—C9—H10108.4
O2—C2—C3123.4 (2)C8—C9—H10108.4
O2—C2—C1117.0 (2)N1—C9—H11108.4
C3—C2—C1119.6 (2)C8—C9—H11108.4
C2—C3—C4121.2 (2)H10—C9—H11107.5
C2—C3—H1119.4C12—N1—C10110.5 (2)
C4—C3—H1119.4C12—N1—C11108.8 (2)
C5—C4—C3118.2 (2)C10—N1—C11107.8 (2)
C5—C4—C8120.0 (2)C12—N1—C9111.23 (19)
C3—C4—C8121.8 (2)C10—N1—C9110.78 (18)
C4—C5—C6121.2 (2)C11—N1—C9107.53 (18)
C4—C5—H2119.4N1—C10—H12109.5
C6—C5—H2119.4N1—C10—H13109.5
C1—C6—C5120.7 (2)H12—C10—H13109.5
C1—C6—H3119.7N1—C10—H14109.5
C5—C6—H3119.7H12—C10—H14109.5
C1—O1—C7116.9 (2)H13—C10—H14109.5
O1—C7—H4109.5N1—C11—H15109.5
O1—C7—H5109.5N1—C11—H16109.5
H4—C7—H5109.5H15—C11—H16109.5
O1—C7—H6109.5N1—C11—H17109.5
H4—C7—H6109.5H15—C11—H17109.5
H5—C7—H6109.5H16—C11—H17109.5
C2—O2—H7113 (2)N1—C12—H18109.5
C9—C8—C4109.59 (18)N1—C12—H19109.5
C9—C8—H8109.8H18—C12—H19109.5
C4—C8—H8109.8N1—C12—H20109.5
C9—C8—H9109.8H18—C12—H20109.5
C4—C8—H9109.8H19—C12—H20109.5
O1—C1—C2—O21.9 (4)C2—C1—C6—C51.6 (4)
C6—C1—C2—O2177.2 (2)C4—C5—C6—C10.7 (4)
O1—C1—C2—C3178.8 (2)C6—C1—O1—C715.1 (4)
C6—C1—C2—C32.1 (4)C2—C1—O1—C7165.8 (3)
O2—C2—C3—C4177.6 (2)C5—C4—C8—C972.0 (3)
C1—C2—C3—C41.6 (4)C3—C4—C8—C9107.9 (3)
C2—C3—C4—C50.6 (4)C4—C8—C9—N1170.0 (2)
C2—C3—C4—C8179.4 (2)C8—C9—N1—C1259.6 (3)
C3—C4—C5—C60.1 (4)C8—C9—N1—C1063.8 (3)
C8—C4—C5—C6179.9 (2)C8—C9—N1—C11178.6 (2)
O1—C1—C6—C5179.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H7···Cl10.88 (4)2.15 (4)3.017 (2)166 (3)
 

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