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The title compound, (+)-4-[hydroxy(1-methyl-5-vinyl-1-azoniabi­cyclo­[2.2.2]­oct-2-yl)­methyl]-1-methyl­quinolinium diiodide, C21H28N2O2+·2I-, is formed from optically active (11S)-(+)-cinchonine and methyl iodide. The N-Me bond lengths are in the range 1.48 (1)-1.49 (1) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803027181/ob6320sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803027181/ob6320Isup2.hkl
Contains datablock I

CCDC reference: 232132

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.010 Å
  • R factor = 0.049
  • wR factor = 0.107
  • Data-to-parameter ratio = 19.8

checkCIF/PLATON results

No syntax errors found



Alert level C SHFSU01_ALERT_2_C The absolute value of parameter shift to su ratio > 0.05 Absolute value of the parameter shift to su ratio given 0.081 Additional refinement cycles may be required. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT080_ALERT_2_C Maximum Shift/Error ............................ 0.08 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.98 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10 PLAT368_ALERT_2_C Short C(sp2)-C(sp2) Bond C20 - C21 = 1.23 Ang. PLAT390_ALERT_3_C Deviating Methyl C10 X-C-H Bond Angle ...... 117.66 Deg. PLAT391_ALERT_3_C Deviating Methyl C10 H-C-H Bond Angle ...... 100.43 Deg. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C21 H28 N2 O PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 I PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 I
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 30.50 From the CIF: _reflns_number_total 5957 Count of symmetry unique reflns 3652 Completeness (_total/calc) 163.12% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2305 Fraction of Friedel pairs measured 0.631 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 3 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: TEXSAN (Molecular Structure Corporation, 2000); program(s) used to solve structure: SIR92 (Altomare et al., 1992); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

(I) top
Crystal data top
C21H28N2O2+·2IF(000) = 564
Mr = 578.27Dx = 1.682 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.7107 Å
a = 8.8608 (5) ÅCell parameters from 14933 reflections
b = 10.9102 (4) Åθ = 1.7–30.5°
c = 12.2876 (5) ŵ = 2.77 mm1
β = 106.018 (2)°T = 296 K
V = 1141.76 (9) Å3Prism, yellow
Z = 20.20 × 0.15 × 0.10 mm
Data collection top
Rigaku R-AXIS RAPID Imaging Plate
diffractometer
4656 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm-1Rint = 0.027
ω scansθmax = 30.5°, θmin = 1.7°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1212
Tmin = 0.559, Tmax = 0.758k = 1315
13000 measured reflectionsl = 1717
5957 independent reflections
Refinement top
Refinement on F2 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.049(Δ/σ)max = 0.081
wR(F2) = 0.107Δρmax = 1.34 e Å3
S = 1.48Δρmin = 0.45 e Å3
4656 reflectionsAbsolute structure: Flack (1983), 2305 Friedel pairs
235 parametersAbsolute structure parameter: 0.02 (3)
H-atom parameters not refined
Special details top

Refinement. Refinement using reflections with F2 > -10.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.11325 (4)0.69411 (4)0.75256 (3)0.0662 (1)
I20.64094 (4)0.17588 (3)0.70539 (3)0.0653 (1)
O10.0142 (4)0.1589 (4)0.8642 (3)0.0564 (10)
N10.2313 (6)0.0613 (5)0.5431 (4)0.058 (1)
N20.1862 (6)0.3694 (4)0.9846 (4)0.055 (1)
C10.1577 (8)0.3791 (6)0.6126 (5)0.056 (2)
C20.2018 (9)0.4427 (6)0.5309 (6)0.069 (2)
C30.259 (1)0.376 (1)0.4513 (7)0.077 (3)
C40.2697 (7)0.2546 (8)0.4555 (5)0.065 (2)
C50.2237 (5)0.1869 (8)0.5397 (3)0.051 (1)
C60.1705 (5)0.2524 (5)0.6223 (4)0.045 (1)
C70.1316 (5)0.1834 (6)0.7095 (3)0.0433 (9)
C80.1413 (7)0.0575 (6)0.7058 (5)0.057 (1)
C90.1908 (9)0.0017 (6)0.6234 (7)0.060 (2)
C100.286 (1)0.008 (1)0.4582 (9)0.091 (3)
C110.0794 (6)0.2446 (5)0.8046 (4)0.044 (1)
C120.2222 (6)0.3036 (4)0.8847 (4)0.0426 (10)
C130.3564 (5)0.2160 (5)0.9340 (4)0.047 (1)
C140.4502 (7)0.2621 (6)1.0490 (5)0.056 (1)
C150.470 (1)0.4007 (8)1.0448 (6)0.078 (2)
C160.314 (1)0.4636 (6)1.0250 (5)0.077 (2)
C170.033 (1)0.4366 (8)0.9520 (7)0.087 (3)
C180.1922 (8)0.2830 (6)1.0814 (4)0.064 (2)
C190.3536 (9)0.2350 (6)1.1338 (5)0.060 (2)
C200.354 (1)0.1009 (7)1.1677 (7)0.081 (2)
C210.460 (1)0.0441 (10)1.2351 (8)0.097 (3)
H10.11640.42360.66570.0718*
H20.18650.52980.52380.0846*
H30.29370.42040.39790.0884*
H40.30910.21600.39930.0740*
H50.11040.01100.76280.0687*
H60.19690.08950.62390.0674*
H70.29080.09300.46490.1170*
H80.22760.01160.37880.1170*
H90.39720.01820.45830.1170*
H100.00350.30600.77320.0519*
H110.07590.12130.81370.0662*
H120.26160.36390.84280.0501*
H130.42240.21060.88540.0566*
H140.31420.13730.94190.0566*
H150.54980.22101.07260.0681*
H160.54140.42661.11160.0939*
H170.51200.41740.98150.0939*
H180.30510.49881.09520.0938*
H190.30170.52750.97090.0938*
H200.01590.47761.01540.1190*
H210.02950.49160.89280.1190*
H220.05100.37680.92610.1190*
H230.15660.32571.13750.0779*
H240.12290.21651.05330.0779*
H250.39700.28031.20070.0687*
H260.26150.05681.12940.0966*
H270.55480.08341.27470.1134*
H280.44650.04141.24860.1134*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0553 (2)0.0589 (2)0.0812 (3)0.0058 (2)0.0134 (2)0.0131 (3)
I20.0513 (2)0.0745 (3)0.0657 (2)0.0026 (2)0.0086 (1)0.0020 (2)
O10.044 (2)0.070 (3)0.058 (2)0.012 (2)0.020 (2)0.012 (2)
N10.063 (3)0.062 (3)0.048 (3)0.001 (2)0.011 (2)0.020 (2)
N20.076 (3)0.044 (2)0.046 (2)0.007 (2)0.019 (2)0.002 (2)
C10.062 (4)0.059 (4)0.041 (3)0.004 (3)0.003 (3)0.002 (3)
C20.084 (5)0.055 (4)0.059 (4)0.015 (3)0.004 (3)0.013 (3)
C30.082 (6)0.103 (7)0.043 (4)0.028 (4)0.009 (3)0.018 (4)
C40.062 (4)0.091 (5)0.042 (3)0.014 (3)0.013 (3)0.002 (3)
C50.043 (2)0.071 (3)0.036 (2)0.011 (3)0.002 (2)0.003 (3)
C60.037 (2)0.054 (3)0.040 (2)0.009 (2)0.002 (2)0.004 (2)
C70.039 (2)0.050 (3)0.038 (2)0.008 (2)0.006 (2)0.005 (3)
C80.067 (4)0.052 (3)0.048 (3)0.008 (2)0.009 (3)0.002 (2)
C90.071 (4)0.044 (3)0.057 (4)0.003 (3)0.007 (3)0.007 (3)
C100.107 (8)0.093 (7)0.076 (6)0.003 (5)0.033 (6)0.020 (5)
C110.039 (2)0.050 (3)0.045 (2)0.001 (2)0.013 (2)0.006 (2)
C120.053 (3)0.039 (2)0.040 (2)0.003 (2)0.020 (2)0.004 (2)
C130.043 (2)0.054 (3)0.045 (2)0.000 (2)0.012 (2)0.003 (2)
C140.056 (3)0.060 (3)0.047 (3)0.008 (2)0.006 (2)0.005 (3)
C150.096 (5)0.072 (5)0.056 (3)0.040 (4)0.002 (3)0.000 (3)
C160.124 (6)0.046 (3)0.048 (3)0.012 (4)0.005 (4)0.004 (3)
C170.103 (6)0.081 (6)0.088 (5)0.043 (5)0.041 (5)0.003 (4)
C180.085 (4)0.069 (4)0.046 (3)0.006 (3)0.030 (3)0.011 (3)
C190.077 (4)0.063 (4)0.034 (3)0.013 (3)0.005 (3)0.001 (2)
C200.101 (6)0.071 (5)0.062 (4)0.006 (4)0.007 (4)0.018 (3)
C210.086 (6)0.102 (6)0.107 (6)0.012 (5)0.036 (5)0.027 (5)
Geometric parameters (Å, º) top
O1—C111.406 (7)C11—C121.516 (6)
O1—H110.958C11—H100.952
N1—C51.37 (1)C12—C131.515 (6)
N1—C91.331 (10)C12—H120.959
N1—C101.48 (1)C13—C141.513 (7)
N2—C121.529 (7)C13—H130.946
N2—C161.507 (9)C13—H140.953
N2—C171.49 (1)C14—C151.52 (1)
N2—C181.507 (8)C14—C191.548 (10)
C1—C21.36 (1)C14—H150.961
C1—C61.389 (8)C15—C161.50 (1)
C1—H10.963C15—H160.932
C2—C31.42 (1)C15—H170.970
C2—H20.961C16—H180.966
C3—C41.33 (1)C16—H190.950
C3—H30.933C17—H200.947
C4—C51.420 (9)C17—H210.937
C4—H40.954C17—H220.976
C5—C61.424 (8)C18—C191.492 (9)
C6—C71.427 (7)C18—H230.954
C7—C81.378 (9)C18—H240.952
C7—C111.525 (8)C19—C201.52 (1)
C8—C91.37 (1)C19—H250.945
C8—H50.964C20—C211.23 (1)
C9—H60.959C20—H260.957
C10—H70.928C21—H270.946
C10—H80.994C21—H280.961
C10—H91.024
I2···O1i3.350 (3)C2···C9iii3.53 (1)
O1···C17ii3.42 (1)C10···C21iv3.54 (2)
C11—O1—H11109.6C11—C12—C13114.5 (4)
C5—N1—C9121.1 (5)C11—C12—H12107.7
C5—N1—C10121.0 (6)C13—C12—H12106.6
C9—N1—C10117.9 (7)C12—C13—C14109.4 (4)
C12—N2—C16106.3 (5)C12—C13—H13109.9
C12—N2—C17112.9 (5)C12—C13—H14108.8
C12—N2—C18111.7 (4)C14—C13—H13109.5
C16—N2—C17107.3 (5)C14—C13—H14109.6
C16—N2—C18107.8 (4)H13—C13—H14109.6
C17—N2—C18110.5 (6)C13—C14—C15109.7 (5)
C2—C1—C6122.4 (7)C13—C14—C19107.6 (5)
C2—C1—H1118.8C13—C14—H15110.4
C6—C1—H1118.7C15—C14—C19107.5 (6)
C1—C2—C3118.4 (7)C15—C14—H15111.7
C1—C2—H2120.6C19—C14—H15109.9
C3—C2—H2120.9C14—C15—C16110.5 (7)
C2—C3—C4121.3 (8)C14—C15—H16109.1
C2—C3—H3117.7C14—C15—H17106.6
C4—C3—H3121.0C16—C15—H16112.2
C3—C4—C5121.1 (7)C16—C15—H17109.0
C3—C4—H4116.6H16—C15—H17109.2
C5—C4—H4122.3N2—C16—C15108.4 (5)
N1—C5—C4121.3 (6)N2—C16—H18109.1
N1—C5—C6120.2 (5)N2—C16—H19109.9
C4—C5—C6118.4 (7)C15—C16—H18109.5
C1—C6—C5118.3 (6)C15—C16—H19111.8
C1—C6—C7123.9 (5)H18—C16—H19108.1
C5—C6—C7117.8 (5)N2—C17—H20110.6
C6—C7—C8118.1 (5)N2—C17—H21111.0
C6—C7—C11122.1 (5)N2—C17—H22108.3
C8—C7—C11119.8 (5)H20—C17—H21110.9
C7—C8—C9122.0 (6)H20—C17—H22107.5
C7—C8—H5117.9H21—C17—H22108.4
C9—C8—H5120.1N2—C18—C19112.4 (6)
N1—C9—C8120.7 (6)N2—C18—H23108.6
N1—C9—H6119.7N2—C18—H24108.1
C8—C9—H6119.6C19—C18—H23109.2
N1—C10—H7117.6C19—C18—H24109.5
N1—C10—H8113.3H23—C18—H24108.9
N1—C10—H9111.0C14—C19—C18106.5 (5)
H7—C10—H8107.6C14—C19—C20114.0 (6)
H7—C10—H9105.2C14—C19—H25108.5
H8—C10—H9100.5C18—C19—C20112.8 (6)
O1—C11—C7111.3 (4)C18—C19—H25107.6
O1—C11—C12109.5 (4)C20—C19—H25107.1
O1—C11—H10109.5C19—C20—C21127.7 (8)
C7—C11—C12107.9 (4)C19—C20—H26114.2
C7—C11—H10109.1C21—C20—H26118.0
C12—C11—H10109.6C20—C21—H27121.2
N2—C12—C11113.5 (4)C20—C21—H28119.5
N2—C12—C13106.9 (4)H27—C21—H28119.2
N2—C12—H12107.3
O1—C11—C7—C6166.6 (4)C6—C7—C8—C91.8 (7)
O1—C11—C7—C813.0 (5)C6—C7—C11—C1273.3 (5)
O1—C11—C12—N259.1 (5)C7—C11—C12—C1357.3 (6)
O1—C11—C12—C1364.0 (6)C8—C7—C11—C12107.1 (5)
N1—C5—C4—C3178.6 (6)C8—C9—N1—C10178.9 (7)
N1—C5—C6—C1177.0 (4)C9—C8—C7—C11178.6 (5)
N1—C5—C6—C72.1 (6)C11—C12—N2—C16156.6 (4)
N1—C9—C8—C70.2 (9)C11—C12—N2—C1739.2 (7)
N2—C12—C11—C7179.7 (4)C11—C12—N2—C1886.1 (5)
N2—C12—C13—C1424.9 (6)C11—C12—C13—C14151.5 (5)
N2—C16—C15—C1415.2 (8)C12—N2—C16—C1552.1 (6)
N2—C18—C19—C1415.6 (6)C12—N2—C18—C1966.1 (6)
N2—C18—C19—C20141.5 (6)C12—C13—C14—C1541.4 (7)
C1—C2—C3—C40 (1)C12—C13—C14—C1975.2 (6)
C1—C6—C5—C43.6 (6)C13—C12—N2—C1676.2 (5)
C1—C6—C7—C8176.4 (5)C13—C12—N2—C17166.4 (5)
C1—C6—C7—C113.2 (7)C13—C12—N2—C1841.1 (6)
C2—C1—C6—C53.5 (8)C13—C14—C15—C1665.8 (7)
C2—C1—C6—C7177.3 (5)C13—C14—C19—C1850.2 (6)
C2—C3—C4—C50 (1)C13—C14—C19—C2074.9 (6)
C3—C2—C1—C61.6 (10)C14—C19—C20—C2177 (1)
C3—C4—C5—C62.0 (8)C15—C14—C19—C1867.9 (6)
C4—C5—N1—C9178.8 (5)C15—C14—C19—C20167.0 (5)
C4—C5—N1—C100.6 (8)C15—C16—N2—C17173.2 (6)
C4—C5—C6—C7177.2 (4)C15—C16—N2—C1867.8 (7)
C5—N1—C9—C80.5 (9)C16—N2—C18—C1950.3 (7)
C5—C6—C7—C82.7 (6)C16—C15—C14—C1950.9 (7)
C5—C6—C7—C11177.7 (4)C17—N2—C18—C19167.2 (5)
C6—C5—N1—C90.6 (7)C18—C19—C20—C21161.2 (10)
C6—C5—N1—C10179.9 (6)C18—C19—C20—C21161.2 (10)
Symmetry codes: (i) x1, y, z; (ii) x, y+1/2, z2; (iii) x, y1/2, z1; (iv) x, y, z+1.
 

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