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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 (11R)-(-)-cinchonidine and methyl iodide. The N-Me bond lengths are in the range of 1.476 (7)-1.497 (6) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804000583/ww6155sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804000583/ww6155Isup2.hkl
Contains datablock I

CCDC reference: 234911

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.050
  • wR factor = 0.084
  • Data-to-parameter ratio = 21.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT094_ALERT_2_B Ratio of Maximum / Minimum Residual Density .... 4.51 PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.88 Ratio
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.43 Ratio PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C20 PLAT368_ALERT_2_C Short C(sp2)-C(sp2) Bond C20 - C21 = 1.22 Ang. 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 6680 Count of symmetry unique reflns 3823 Completeness (_total/calc) 174.73% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2857 Fraction of Friedel pairs measured 0.747 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 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 4 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) = 1128
Mr = 578.27Dx = 1.709 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2ac 2abCell parameters from 29792 reflections
a = 11.3103 (4) Åθ = 1.4–30.5°
b = 13.3106 (3) ŵ = 2.81 mm1
c = 14.9280 (5) ÅT = 296 K
V = 2247.4 (1) Å3Prism, yellow
Z = 40.20 × 0.16 × 0.10 mm
Data collection top
Rigaku R-AXIS RAPID Imaging Plate
diffractometer
5056 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm-1Rint = 0.046
ω scansθmax = 30.5°, θmin = 1.7°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1516
Tmin = 0.619, Tmax = 0.755k = 1818
26613 measured reflectionsl = 2121
6680 independent reflections
Refinement top
Refinement on F2 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.050(Δ/σ)max = 0.013
wR(F2) = 0.084Δρmax = 1.76 e Å3
S = 1.10Δρmin = 0.39 e Å3
5056 reflectionsAbsolute structure: Flack (1983), 2857 Friedel pairs [CHECK]
235 parametersAbsolute structure parameter: 0.01 (2)
H-atom parameters constrained
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
I10.47477 (3)0.19712 (2)0.03022 (2)0.05140 (9)
I20.49191 (3)0.22709 (2)0.46580 (2)0.0591 (1)
O10.3889 (3)0.1533 (2)0.2192 (2)0.0476 (7)
N10.6937 (3)0.0112 (3)0.4073 (3)0.0456 (9)
N20.2413 (3)0.0067 (3)0.1359 (2)0.0397 (8)
C10.6283 (4)0.0978 (3)0.1783 (3)0.0376 (9)
C20.7162 (4)0.1646 (3)0.1657 (3)0.0433 (10)
C30.8004 (4)0.1815 (3)0.2333 (3)0.046 (1)
C40.7932 (4)0.1331 (3)0.3135 (3)0.046 (1)
C50.7021 (4)0.0626 (3)0.3276 (3)0.0370 (9)
C60.6178 (4)0.0430 (3)0.2598 (3)0.0340 (8)
C70.5301 (4)0.0318 (3)0.2739 (2)0.0359 (8)
C80.5303 (4)0.0829 (3)0.3538 (3)0.0449 (9)
C90.6114 (4)0.0592 (3)0.4189 (3)0.050 (1)
C100.7745 (5)0.0362 (4)0.4817 (4)0.068 (1)
C110.4377 (4)0.0574 (3)0.2029 (3)0.0383 (9)
C120.3414 (4)0.0235 (3)0.2049 (3)0.0340 (8)
C130.2815 (4)0.0371 (3)0.2964 (3)0.0421 (10)
C140.1554 (4)0.0737 (4)0.2835 (3)0.050 (1)
C150.0821 (4)0.0150 (4)0.2495 (4)0.057 (1)
C160.1470 (4)0.0651 (4)0.1720 (3)0.051 (1)
C170.2846 (4)0.0325 (4)0.0478 (3)0.051 (1)
C180.1856 (4)0.1079 (3)0.1221 (3)0.048 (1)
C190.1514 (4)0.1565 (4)0.2124 (4)0.051 (1)
C200.2242 (5)0.2469 (4)0.2349 (4)0.068 (2)
C210.2050 (9)0.3099 (7)0.2923 (7)0.132 (4)
H10.57300.08630.13110.0436*
H20.71980.20160.11020.0485*
H30.86310.22850.22310.0531*
H40.84970.14790.36000.0558*
H50.47090.13430.36310.0533*
H60.61060.09490.47490.0594*
H70.77480.10760.49090.0760*
H80.74830.00330.53530.0760*
H90.85300.01410.46720.0760*
H100.47380.05840.14380.0448*
H110.45060.20200.21780.0539*
H120.37900.08530.18940.0410*
H130.28350.02380.32820.0497*
H140.32690.08670.33000.0497*
H150.12390.10030.33830.0587*
H160.06950.06260.29690.0679*
H170.00530.00740.22950.0679*
H180.18520.12580.19150.0581*
H190.09410.08210.12430.0581*
H200.21910.03950.00790.0576*
H210.32030.09660.05600.0576*
H220.34020.01260.02310.0576*
H230.11600.09960.08540.0546*
H240.23950.15010.09090.0546*
H250.06920.17640.20600.0614*
H260.29190.26100.19730.0779*
H270.14080.30110.33380.1405*
H280.25830.36530.30300.1405*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0691 (2)0.0450 (1)0.0400 (1)0.0006 (1)0.0026 (2)0.0072 (1)
I20.0593 (2)0.0541 (2)0.0638 (2)0.0009 (1)0.0125 (2)0.0088 (1)
O10.052 (2)0.033 (1)0.058 (2)0.004 (1)0.001 (2)0.001 (1)
N10.049 (2)0.047 (2)0.040 (2)0.010 (2)0.012 (2)0.003 (2)
N20.047 (2)0.040 (2)0.032 (2)0.006 (2)0.005 (1)0.004 (1)
C10.044 (2)0.036 (2)0.033 (2)0.001 (2)0.001 (2)0.001 (2)
C20.047 (2)0.041 (2)0.042 (2)0.001 (2)0.015 (2)0.001 (2)
C30.035 (2)0.041 (2)0.063 (3)0.001 (2)0.008 (2)0.006 (2)
C40.038 (2)0.044 (2)0.058 (3)0.005 (2)0.004 (2)0.010 (2)
C50.037 (2)0.033 (2)0.041 (2)0.011 (2)0.001 (2)0.004 (2)
C60.038 (2)0.032 (2)0.032 (2)0.007 (2)0.001 (2)0.002 (2)
C70.040 (2)0.033 (2)0.035 (2)0.004 (2)0.004 (2)0.001 (1)
C80.054 (2)0.038 (2)0.042 (2)0.001 (2)0.001 (2)0.010 (2)
C90.064 (3)0.046 (2)0.040 (2)0.005 (2)0.006 (2)0.017 (2)
C100.077 (3)0.076 (4)0.052 (3)0.006 (3)0.026 (3)0.004 (3)
C110.043 (2)0.038 (2)0.034 (2)0.005 (2)0.001 (2)0.001 (2)
C120.034 (2)0.036 (2)0.032 (2)0.007 (2)0.000 (2)0.004 (2)
C130.053 (3)0.045 (2)0.028 (2)0.007 (2)0.001 (2)0.003 (2)
C140.049 (3)0.058 (3)0.042 (3)0.002 (2)0.013 (2)0.000 (2)
C150.046 (3)0.064 (3)0.062 (3)0.007 (2)0.008 (2)0.016 (2)
C160.047 (3)0.047 (3)0.057 (3)0.014 (2)0.009 (2)0.003 (2)
C170.068 (3)0.057 (3)0.028 (2)0.004 (2)0.004 (2)0.005 (2)
C180.051 (3)0.047 (2)0.045 (3)0.003 (2)0.001 (2)0.008 (2)
C190.044 (2)0.049 (3)0.061 (3)0.008 (2)0.002 (2)0.002 (2)
C200.065 (3)0.049 (3)0.088 (4)0.000 (3)0.017 (3)0.010 (3)
C210.145 (8)0.116 (6)0.136 (7)0.057 (6)0.057 (6)0.059 (6)
Geometric parameters (Å, º) top
O1—C111.411 (5)C11—C121.531 (6)
O1—H110.953C11—H100.973
N1—C51.376 (6)C12—C131.536 (6)
N1—C91.332 (6)C12—H120.956
N1—C101.476 (7)C13—C141.520 (7)
N2—C121.547 (5)C13—H130.939
N2—C161.529 (6)C13—H140.976
N2—C171.497 (6)C14—C151.530 (7)
N2—C181.501 (6)C14—C191.530 (7)
C1—C21.347 (6)C14—H150.959
C1—C61.423 (5)C15—C161.524 (7)
C1—H10.954C15—H160.960
C2—C31.406 (6)C15—H170.966
C2—H20.965C16—H180.961
C3—C41.362 (7)C16—H190.958
C3—H30.958C17—H200.955
C4—C51.410 (6)C17—H210.952
C4—H40.964C17—H220.945
C5—C61.415 (6)C18—C191.544 (7)
C6—C71.421 (5)C18—H230.965
C7—C81.373 (5)C18—H240.951
C7—C111.527 (6)C19—C201.497 (7)
C8—C91.373 (6)C19—H250.972
C8—H50.969C20—C211.22 (1)
C9—H60.962C20—H260.968
C10—H70.960C21—H270.962
C10—H80.960C21—H280.965
C10—H90.960
I2···O1i3.461 (3)O1···C2ii3.200 (5)
O1···C3ii3.151 (5)O1···C4ii3.545 (5)
C11—O1—H11109.0C11—C12—C13114.5 (3)
C5—N1—C9120.7 (4)C11—C12—H12106.5
C5—N1—C10119.7 (4)C13—C12—H12108.1
C9—N1—C10119.6 (4)C12—C13—C14109.8 (3)
C12—N2—C16111.5 (3)C12—C13—H13109.7
C12—N2—C17113.3 (3)C12—C13—H14107.7
C12—N2—C18105.6 (3)C14—C13—H13111.3
C16—N2—C17108.6 (3)C14—C13—H14110.0
C16—N2—C18108.4 (3)H13—C13—H14108.2
C17—N2—C18109.2 (3)C13—C14—C15107.6 (4)
C2—C1—C6121.3 (4)C13—C14—C19110.3 (4)
C2—C1—H1119.1C13—C14—H15111.1
C6—C1—H1119.6C15—C14—C19108.0 (4)
C1—C2—C3120.4 (4)C15—C14—H15111.5
C1—C2—H2119.2C19—C14—H15108.3
C3—C2—H2120.4C14—C15—C16109.2 (4)
C2—C3—C4121.0 (4)C14—C15—H16110.2
C2—C3—H3119.5C14—C15—H17110.6
C4—C3—H3119.5C16—C15—H16110.0
C3—C4—C5119.3 (4)C16—C15—H17109.5
C3—C4—H4119.9H16—C15—H17107.3
C5—C4—H4120.8N2—C16—C15109.3 (4)
N1—C5—C4120.7 (4)N2—C16—H18108.6
N1—C5—C6118.7 (4)N2—C16—H19108.7
C4—C5—C6120.5 (4)C15—C16—H18110.7
C1—C6—C5117.4 (4)C15—C16—H19111.5
C1—C6—C7123.0 (3)H18—C16—H19107.9
C5—C6—C7119.6 (3)N2—C17—H20109.2
C6—C7—C8118.4 (4)N2—C17—H21109.8
C6—C7—C11122.1 (3)N2—C17—H22109.8
C8—C7—C11119.5 (4)H20—C17—H21108.8
C7—C8—C9120.1 (4)H20—C17—H22109.5
C7—C8—H5118.3H21—C17—H22109.7
C9—C8—H5121.6N2—C18—C19111.2 (4)
N1—C9—C8122.5 (4)N2—C18—H23108.5
N1—C9—H6117.9N2—C18—H24109.2
C8—C9—H6119.7C19—C18—H23109.8
N1—C10—H7109.5C19—C18—H24110.0
N1—C10—H8109.5H23—C18—H24108.1
N1—C10—H9109.5C14—C19—C18107.3 (4)
H7—C10—H8109.5C14—C19—C20114.0 (4)
H7—C10—H9109.5C14—C19—H25107.0
H8—C10—H9109.5C18—C19—C20113.3 (4)
O1—C11—C7110.5 (3)C18—C19—H25105.5
O1—C11—C12110.8 (3)C20—C19—H25109.2
O1—C11—H10108.0C19—C20—C21127.8 (7)
C7—C11—C12108.4 (3)C19—C20—H26117.4
C7—C11—H10110.1C21—C20—H26114.6
C12—C11—H10109.0C20—C21—H27120.2
N2—C12—C11114.0 (3)C20—C21—H28122.0
N2—C12—C13106.6 (3)H27—C21—H28117.3
N2—C12—H12106.8
O1—C11—C7—C6160.0 (3)C6—C7—C8—C92.0 (6)
O1—C11—C7—C819.2 (5)C6—C7—C11—C1278.4 (4)
O1—C11—C12—N258.5 (4)C7—C11—C12—C1356.9 (4)
O1—C11—C12—C1364.6 (4)C8—C7—C11—C12102.3 (4)
N1—C5—C4—C3178.8 (4)C8—C9—N1—C10177.1 (4)
N1—C5—C6—C1179.6 (4)C9—C8—C7—C11178.7 (4)
N1—C5—C6—C72.5 (6)C11—C12—N2—C1684.2 (4)
N1—C9—C8—C71.5 (7)C11—C12—N2—C1738.7 (4)
N2—C12—C11—C7179.9 (3)C11—C12—N2—C18158.2 (3)
N2—C12—C13—C1424.2 (4)C11—C12—C13—C14151.1 (4)
N2—C16—C15—C1417.2 (5)C12—N2—C16—C1567.5 (4)
N2—C18—C19—C1414.9 (5)C12—N2—C18—C1951.8 (4)
N2—C18—C19—C20111.8 (4)C12—C13—C14—C1573.8 (5)
C1—C2—C3—C41.9 (7)C12—C13—C14—C1943.8 (5)
C1—C6—C5—C40.9 (6)C13—C12—N2—C1643.0 (4)
C1—C6—C7—C8177.7 (4)C13—C12—N2—C17165.9 (3)
C1—C6—C7—C111.5 (6)C13—C12—N2—C1874.5 (4)
C2—C1—C6—C51.2 (6)C13—C14—C15—C1648.6 (5)
C2—C1—C6—C7176.7 (4)C13—C14—C19—C1866.2 (5)
C2—C3—C4—C52.1 (7)C13—C14—C19—C2060.1 (5)
C3—C2—C1—C60.2 (6)C14—C19—C20—C2170.8 (9)
C3—C4—C5—C60.7 (6)C15—C14—C19—C1851.2 (5)
C4—C5—N1—C9176.4 (4)C15—C14—C19—C20177.4 (4)
C4—C5—N1—C105.4 (6)C15—C16—N2—C17167.0 (4)
C4—C5—C6—C7177.0 (4)C15—C16—N2—C1848.4 (5)
C5—N1—C9—C81.1 (7)C16—N2—C18—C1967.8 (4)
C5—C6—C7—C80.0 (6)C16—C15—C14—C1970.5 (5)
C5—C6—C7—C11179.3 (4)C17—N2—C18—C19174.0 (4)
C6—C5—N1—C93.1 (6)C18—C19—C20—C21166.1 (8)
C6—C5—N1—C10175.1 (4)C18—C19—C20—C21166.1 (8)
Symmetry codes: (i) x1, y+1/2, z1/2; (ii) x1, y1/2, z1/2.
 

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