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The N-containing ring of the tetra­hydro­isoquinolinium ion of the title compound, C19H24NO3+·SCN, has a half-chair conformation. There is a network of hydrogen bonds between the phenolic groups and thio­cyanate anions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807005879/cf2079sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807005879/cf2079Isup2.hkl
Contains datablock I

CCDC reference: 640291

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.033
  • wR factor = 0.085
  • Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT031_ALERT_4_B Refined Extinction Parameter within Range ...... 1.86 Sigma
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

6-Hydroxy-1-(4-hydroxybenzyl)-7-methoxy-2,2-dimethyl-1,2,3,4- tetrahydroisoquinolinium thiocyanate top
Crystal data top
C19H24NO3+·SCNF(000) = 792
Mr = 372.47Dx = 1.345 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.8059 (18) ÅCell parameters from 5242 reflections
b = 9.7744 (13) Åθ = 2.6–29.6°
c = 14.1049 (18) ŵ = 0.20 mm1
β = 104.938 (2)°T = 273 K
V = 1839.1 (4) Å3Block, colourless
Z = 40.52 × 0.47 × 0.32 mm
Data collection top
Bruker SMART CCD
diffractometer
3135 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.014
Graphite monochromatorθmax = 26.0°, θmin = 2.6°
φ and ω scansh = 1617
10178 measured reflectionsk = 812
3593 independent reflectionsl = 1717
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)] = 0.033H-atom parameters constrained
wR(F2) = 0.085 w = 1/[σ2(Fo2) + (0.0372P)2 + 0.8143P]
where P = (Fo2 + 2Fc2)/3
S = 0.95(Δ/σ)max < 0.001
3593 reflectionsΔρmax = 0.22 e Å3
241 parametersΔρmin = 0.16 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0013 (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
C60.39894 (10)1.13914 (15)0.09207 (10)0.0367 (3)
H60.39781.19250.03720.044*
C30.40928 (11)0.98264 (15)0.25638 (10)0.0378 (3)
H30.41530.92910.31210.045*
C20.39675 (10)0.92105 (15)0.16546 (10)0.0362 (3)
H20.39310.82620.16070.043*
C40.41278 (10)1.12346 (15)0.26428 (10)0.0359 (3)
C10.38957 (9)0.99834 (14)0.08179 (10)0.0322 (3)
N20.23738 (8)0.91813 (13)0.18402 (8)0.0346 (3)
C110.16156 (9)0.98652 (14)0.04769 (9)0.0293 (3)
H110.19491.06870.06660.035*
C130.25938 (10)0.96808 (14)0.07758 (9)0.0303 (3)
H130.25311.06800.07930.036*
C80.06129 (10)0.74527 (15)0.00981 (10)0.0353 (3)
H80.02760.66330.02880.042*
C100.09419 (9)0.93951 (14)0.09679 (9)0.0297 (3)
C70.13011 (10)0.79169 (14)0.05991 (9)0.0306 (3)
C150.14030 (11)0.71585 (15)0.14979 (10)0.0385 (3)
H15A0.14880.61910.13450.046*
H15B0.07890.72670.20140.046*
C140.22725 (11)0.76464 (15)0.18701 (10)0.0387 (3)
H14A0.28860.72430.14740.046*
H14B0.21830.73350.25400.046*
C170.14254 (12)0.98473 (17)0.24234 (11)0.0451 (4)
H17A0.15411.08070.24900.068*
H17B0.09060.97260.20910.068*
H17C0.12230.94350.30620.068*
C180.31960 (13)0.9576 (2)0.23044 (12)0.0524 (4)
H18A0.29810.94130.29980.079*
H18B0.37820.90380.20260.079*
H18C0.33511.05280.21860.079*
O10.41825 (9)1.19052 (12)0.35059 (8)0.0515 (3)
H10.40981.13580.39180.077*
O20.07185 (7)1.00571 (11)0.17409 (7)0.0393 (2)
O30.02596 (8)0.77673 (13)0.11592 (7)0.0476 (3)
H3A0.06760.72650.08050.071*
C190.13020 (12)1.12271 (18)0.21127 (11)0.0480 (4)
H19A0.19961.09740.23240.072*
H19B0.10901.15900.26590.072*
H19C0.12141.19080.16070.072*
C120.18067 (9)0.91251 (13)0.03035 (9)0.0276 (3)
C90.04213 (10)0.81766 (15)0.06685 (9)0.0336 (3)
C160.36691 (10)0.93333 (16)0.01869 (10)0.0374 (3)
H16A0.37430.83490.01200.045*
H16B0.41420.96620.05370.045*
C50.40994 (11)1.20207 (15)0.18186 (11)0.0384 (3)
H50.41541.29680.18700.046*
S10.36127 (3)0.01363 (4)0.51510 (3)0.04728 (13)
N10.17909 (13)0.1212 (2)0.49360 (14)0.0771 (5)
C200.25418 (13)0.06578 (17)0.50175 (11)0.0469 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C60.0349 (7)0.0397 (8)0.0362 (7)0.0023 (6)0.0106 (6)0.0044 (6)
C30.0382 (8)0.0410 (8)0.0341 (7)0.0009 (6)0.0090 (6)0.0059 (6)
C20.0346 (7)0.0320 (7)0.0419 (8)0.0003 (6)0.0095 (6)0.0001 (6)
C40.0310 (7)0.0415 (8)0.0350 (7)0.0025 (6)0.0080 (5)0.0057 (6)
C10.0236 (6)0.0393 (8)0.0344 (7)0.0010 (5)0.0086 (5)0.0020 (6)
N20.0372 (6)0.0425 (7)0.0271 (6)0.0017 (5)0.0138 (5)0.0000 (5)
C110.0275 (6)0.0324 (7)0.0283 (6)0.0002 (5)0.0079 (5)0.0013 (5)
C130.0334 (7)0.0330 (7)0.0275 (6)0.0001 (5)0.0129 (5)0.0030 (5)
C80.0371 (7)0.0338 (7)0.0328 (7)0.0072 (6)0.0052 (6)0.0025 (6)
C100.0273 (6)0.0389 (7)0.0234 (6)0.0044 (5)0.0074 (5)0.0021 (5)
C70.0322 (7)0.0327 (7)0.0262 (6)0.0018 (5)0.0061 (5)0.0012 (5)
C150.0466 (8)0.0355 (8)0.0329 (7)0.0023 (6)0.0094 (6)0.0048 (6)
C140.0456 (8)0.0412 (8)0.0299 (7)0.0071 (6)0.0109 (6)0.0076 (6)
C170.0506 (9)0.0508 (9)0.0327 (7)0.0087 (7)0.0083 (6)0.0079 (7)
C180.0556 (10)0.0718 (12)0.0395 (8)0.0051 (9)0.0296 (7)0.0004 (8)
O10.0683 (8)0.0501 (7)0.0388 (6)0.0073 (6)0.0190 (5)0.0105 (5)
O20.0393 (5)0.0514 (6)0.0323 (5)0.0008 (5)0.0183 (4)0.0048 (4)
O30.0448 (6)0.0644 (8)0.0377 (5)0.0173 (5)0.0182 (5)0.0038 (5)
C190.0481 (9)0.0590 (10)0.0407 (8)0.0037 (8)0.0185 (7)0.0173 (7)
C120.0255 (6)0.0326 (7)0.0251 (6)0.0023 (5)0.0073 (5)0.0021 (5)
C90.0293 (6)0.0442 (8)0.0272 (6)0.0019 (6)0.0073 (5)0.0093 (6)
C160.0307 (7)0.0462 (8)0.0378 (7)0.0004 (6)0.0133 (6)0.0063 (6)
C50.0395 (8)0.0321 (7)0.0447 (8)0.0034 (6)0.0126 (6)0.0015 (6)
S10.0490 (2)0.0497 (3)0.0427 (2)0.00986 (18)0.01127 (17)0.00314 (17)
N10.0564 (10)0.0831 (13)0.0873 (13)0.0238 (9)0.0106 (9)0.0077 (10)
C200.0516 (9)0.0484 (9)0.0392 (8)0.0043 (8)0.0090 (7)0.0029 (7)
Geometric parameters (Å, º) top
C6—C51.381 (2)C7—C121.3804 (19)
C6—C11.386 (2)C7—C151.5062 (18)
C6—H60.930C15—C141.506 (2)
C3—C41.381 (2)C15—H15A0.970
C3—C21.386 (2)C15—H15B0.970
C3—H30.930C14—H14A0.970
C2—C11.3831 (19)C14—H14B0.970
C2—H20.930C17—H17A0.960
C4—O11.3675 (17)C17—H17B0.960
C4—C51.386 (2)C17—H17C0.960
C1—C161.5104 (19)C18—H18A0.960
N2—C181.4998 (18)C18—H18B0.960
N2—C171.5031 (19)C18—H18C0.960
N2—C141.5064 (19)O1—H10.820
N2—C131.5329 (16)O2—C191.4191 (18)
C11—C101.3741 (18)O3—C91.3631 (15)
C11—C121.3979 (17)O3—H3A0.820
C11—H110.930C19—H19A0.960
C13—C121.5142 (17)C19—H19B0.960
C13—C161.5406 (19)C19—H19C0.960
C13—H130.980C16—H16A0.970
C8—C91.374 (2)C16—H16B0.970
C8—C71.3978 (19)C5—H50.930
C8—H80.930S1—C201.6372 (17)
C10—O21.3697 (15)N1—C201.149 (2)
C10—C91.399 (2)
C5—C6—C1121.56 (13)H15A—C15—H15B107.8
C5—C6—H6119.2N2—C14—C15112.47 (11)
C1—C6—H6119.2N2—C14—H14A109.1
C4—C3—C2120.06 (13)C15—C14—H14A109.1
C4—C3—H3120.0N2—C14—H14B109.1
C2—C3—H3120.0C15—C14—H14B109.1
C1—C2—C3121.10 (13)H14A—C14—H14B107.8
C1—C2—H2119.5N2—C17—H17A109.5
C3—C2—H2119.5N2—C17—H17B109.5
O1—C4—C3122.85 (13)H17A—C17—H17B109.5
O1—C4—C5117.66 (13)N2—C17—H17C109.5
C3—C4—C5119.49 (13)H17A—C17—H17C109.5
C6—C1—C2117.95 (13)H17B—C17—H17C109.5
C6—C1—C16120.46 (13)N2—C18—H18A109.5
C2—C1—C16121.52 (13)N2—C18—H18B109.5
C18—N2—C17107.48 (12)H18A—C18—H18B109.5
C18—N2—C14108.60 (12)N2—C18—H18C109.5
C17—N2—C14110.76 (12)H18A—C18—H18C109.5
C18—N2—C13111.38 (11)H18B—C18—H18C109.5
C17—N2—C13108.83 (10)C4—O1—H1109.5
C14—N2—C13109.77 (10)C10—O2—C19116.87 (11)
C10—C11—C12120.89 (12)C9—O3—H3A109.5
C10—C11—H11119.6O2—C19—H19A109.5
C12—C11—H11119.6O2—C19—H19B109.5
C12—C13—N2109.46 (10)H19A—C19—H19B109.5
C12—C13—C16112.63 (11)O2—C19—H19C109.5
N2—C13—C16112.21 (10)H19A—C19—H19C109.5
C12—C13—H13107.4H19B—C19—H19C109.5
N2—C13—H13107.4C7—C12—C11119.81 (12)
C16—C13—H13107.4C7—C12—C13122.57 (11)
C9—C8—C7121.64 (13)C11—C12—C13117.60 (11)
C9—C8—H8119.2O3—C9—C8123.12 (13)
C7—C8—H8119.2O3—C9—C10117.68 (12)
O2—C10—C11124.32 (12)C8—C9—C10119.20 (12)
O2—C10—C9116.04 (11)C1—C16—C13110.54 (11)
C11—C10—C9119.63 (12)C1—C16—H16A109.5
C12—C7—C8118.80 (12)C13—C16—H16A109.5
C12—C7—C15121.71 (12)C1—C16—H16B109.5
C8—C7—C15119.27 (12)C13—C16—H16B109.5
C14—C15—C7113.16 (12)H16A—C16—H16B108.1
C14—C15—H15A108.9C6—C5—C4119.68 (14)
C7—C15—H15A108.9C6—C5—H5120.2
C14—C15—H15B108.9C4—C5—H5120.2
C7—C15—H15B108.9N1—C20—S1179.14 (17)
C4—C3—C2—C11.3 (2)C9—C10—O2—C19174.47 (12)
C2—C3—C4—O1175.51 (13)C8—C7—C12—C110.73 (19)
C2—C3—C4—C54.0 (2)C15—C7—C12—C11173.70 (12)
C5—C6—C1—C23.3 (2)C8—C7—C12—C13177.62 (12)
C5—C6—C1—C16173.63 (12)C15—C7—C12—C137.95 (19)
C3—C2—C1—C62.3 (2)C10—C11—C12—C71.14 (19)
C3—C2—C1—C16174.58 (12)C10—C11—C12—C13177.29 (12)
C18—N2—C13—C12173.67 (12)N2—C13—C12—C727.51 (17)
C17—N2—C13—C1268.01 (14)C16—C13—C12—C798.06 (14)
C14—N2—C13—C1253.36 (14)N2—C13—C12—C11154.11 (11)
C18—N2—C13—C1647.86 (16)C16—C13—C12—C1180.32 (15)
C17—N2—C13—C16166.18 (12)C7—C8—C9—O3178.62 (13)
C14—N2—C13—C1672.45 (14)C7—C8—C9—C101.3 (2)
C12—C11—C10—O2179.67 (11)O2—C10—C9—O30.59 (18)
C12—C11—C10—C91.58 (19)C11—C10—C9—O3178.26 (12)
C9—C8—C7—C120.8 (2)O2—C10—C9—C8179.52 (12)
C9—C8—C7—C15173.75 (13)C11—C10—C9—C81.63 (19)
C12—C7—C15—C1414.08 (19)C6—C1—C16—C1368.99 (16)
C8—C7—C15—C14171.50 (12)C2—C1—C16—C13107.81 (15)
C18—N2—C14—C15175.05 (12)C12—C13—C16—C162.56 (15)
C17—N2—C14—C1557.24 (15)N2—C13—C16—C1173.38 (11)
C13—N2—C14—C1562.97 (14)C1—C6—C5—C40.7 (2)
C7—C15—C14—N241.54 (16)O1—C4—C5—C6176.50 (13)
C11—C10—O2—C196.74 (19)C3—C4—C5—C63.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···N1i0.821.922.735 (2)172
O1—H1···S1ii0.822.493.3054 (12)172
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y+1, z.
 

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