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
CCDC reference: 234911
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (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
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.
Crystal data top
C21H28N2O2+·2I− | F(000) = 1128 |
Mr = 578.27 | Dx = 1.709 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 29792 reflections |
a = 11.3103 (4) Å | θ = 1.4–30.5° |
b = 13.3106 (3) Å | µ = 2.81 mm−1 |
c = 14.9280 (5) Å | T = 296 K |
V = 2247.4 (1) Å3 | Prism, yellow |
Z = 4 | 0.20 × 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-1 | Rint = 0.046 |
ω scans | θmax = 30.5°, θmin = 1.7° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −15→16 |
Tmin = 0.619, Tmax = 0.755 | k = −18→18 |
26613 measured reflections | l = −21→21 |
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) = 0.084 | Δρmax = 1.76 e Å−3 |
S = 1.10 | Δρmin = −0.39 e Å−3 |
5056 reflections | Absolute structure: Flack (1983), 2857 Friedel pairs [CHECK] |
235 parameters | Absolute 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 | x | y | z | Uiso*/Ueq | |
I1 | −0.47477 (3) | 0.19712 (2) | 0.03022 (2) | 0.05140 (9) | |
I2 | −0.49191 (3) | 0.22709 (2) | −0.46580 (2) | 0.0591 (1) | |
O1 | −0.3889 (3) | −0.1533 (2) | −0.2192 (2) | 0.0476 (7) | |
N1 | −0.6937 (3) | 0.0112 (3) | −0.4073 (3) | 0.0456 (9) | |
N2 | −0.2413 (3) | 0.0067 (3) | −0.1359 (2) | 0.0397 (8) | |
C1 | −0.6283 (4) | 0.0978 (3) | −0.1783 (3) | 0.0376 (9) | |
C2 | −0.7162 (4) | 0.1646 (3) | −0.1657 (3) | 0.0433 (10) | |
C3 | −0.8004 (4) | 0.1815 (3) | −0.2333 (3) | 0.046 (1) | |
C4 | −0.7932 (4) | 0.1331 (3) | −0.3135 (3) | 0.046 (1) | |
C5 | −0.7021 (4) | 0.0626 (3) | −0.3276 (3) | 0.0370 (9) | |
C6 | −0.6178 (4) | 0.0430 (3) | −0.2598 (3) | 0.0340 (8) | |
C7 | −0.5301 (4) | −0.0318 (3) | −0.2739 (2) | 0.0359 (8) | |
C8 | −0.5303 (4) | −0.0829 (3) | −0.3538 (3) | 0.0449 (9) | |
C9 | −0.6114 (4) | −0.0592 (3) | −0.4189 (3) | 0.050 (1) | |
C10 | −0.7745 (5) | 0.0362 (4) | −0.4817 (4) | 0.068 (1) | |
C11 | −0.4377 (4) | −0.0574 (3) | −0.2029 (3) | 0.0383 (9) | |
C12 | −0.3414 (4) | 0.0235 (3) | −0.2049 (3) | 0.0340 (8) | |
C13 | −0.2815 (4) | 0.0371 (3) | −0.2964 (3) | 0.0421 (10) | |
C14 | −0.1554 (4) | 0.0737 (4) | −0.2835 (3) | 0.050 (1) | |
C15 | −0.0821 (4) | −0.0150 (4) | −0.2495 (4) | 0.057 (1) | |
C16 | −0.1470 (4) | −0.0651 (4) | −0.1720 (3) | 0.051 (1) | |
C17 | −0.2846 (4) | −0.0325 (4) | −0.0478 (3) | 0.051 (1) | |
C18 | −0.1856 (4) | 0.1079 (3) | −0.1221 (3) | 0.048 (1) | |
C19 | −0.1514 (4) | 0.1565 (4) | −0.2124 (4) | 0.051 (1) | |
C20 | −0.2242 (5) | 0.2469 (4) | −0.2349 (4) | 0.068 (2) | |
C21 | −0.2050 (9) | 0.3099 (7) | −0.2923 (7) | 0.132 (4) | |
H1 | −0.5730 | 0.0863 | −0.1311 | 0.0436* | |
H2 | −0.7198 | 0.2016 | −0.1102 | 0.0485* | |
H3 | −0.8631 | 0.2285 | −0.2231 | 0.0531* | |
H4 | −0.8497 | 0.1479 | −0.3600 | 0.0558* | |
H5 | −0.4709 | −0.1343 | −0.3631 | 0.0533* | |
H6 | −0.6106 | −0.0949 | −0.4749 | 0.0594* | |
H7 | −0.7748 | 0.1076 | −0.4909 | 0.0760* | |
H8 | −0.7483 | 0.0033 | −0.5353 | 0.0760* | |
H9 | −0.8530 | 0.0141 | −0.4672 | 0.0760* | |
H10 | −0.4738 | −0.0584 | −0.1438 | 0.0448* | |
H11 | −0.4506 | −0.2020 | −0.2178 | 0.0539* | |
H12 | −0.3790 | 0.0853 | −0.1894 | 0.0410* | |
H13 | −0.2835 | −0.0238 | −0.3282 | 0.0497* | |
H14 | −0.3269 | 0.0867 | −0.3300 | 0.0497* | |
H15 | −0.1239 | 0.1003 | −0.3383 | 0.0587* | |
H16 | −0.0695 | −0.0626 | −0.2969 | 0.0679* | |
H17 | −0.0053 | 0.0074 | −0.2295 | 0.0679* | |
H18 | −0.1852 | −0.1258 | −0.1915 | 0.0581* | |
H19 | −0.0941 | −0.0821 | −0.1243 | 0.0581* | |
H20 | −0.2191 | −0.0395 | −0.0079 | 0.0576* | |
H21 | −0.3203 | −0.0966 | −0.0560 | 0.0576* | |
H22 | −0.3402 | 0.0126 | −0.0231 | 0.0576* | |
H23 | −0.1160 | 0.0996 | −0.0854 | 0.0546* | |
H24 | −0.2395 | 0.1501 | −0.0909 | 0.0546* | |
H25 | −0.0692 | 0.1764 | −0.2060 | 0.0614* | |
H26 | −0.2919 | 0.2610 | −0.1973 | 0.0779* | |
H27 | −0.1408 | 0.3011 | −0.3338 | 0.1405* | |
H28 | −0.2583 | 0.3653 | −0.3030 | 0.1405* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.0691 (2) | 0.0450 (1) | 0.0400 (1) | 0.0006 (1) | −0.0026 (2) | −0.0072 (1) |
I2 | 0.0593 (2) | 0.0541 (2) | 0.0638 (2) | 0.0009 (1) | 0.0125 (2) | −0.0088 (1) |
O1 | 0.052 (2) | 0.033 (1) | 0.058 (2) | 0.004 (1) | 0.001 (2) | −0.001 (1) |
N1 | 0.049 (2) | 0.047 (2) | 0.040 (2) | −0.010 (2) | −0.012 (2) | −0.003 (2) |
N2 | 0.047 (2) | 0.040 (2) | 0.032 (2) | 0.006 (2) | −0.005 (1) | −0.004 (1) |
C1 | 0.044 (2) | 0.036 (2) | 0.033 (2) | −0.001 (2) | 0.001 (2) | 0.001 (2) |
C2 | 0.047 (2) | 0.041 (2) | 0.042 (2) | 0.001 (2) | 0.015 (2) | −0.001 (2) |
C3 | 0.035 (2) | 0.041 (2) | 0.063 (3) | 0.001 (2) | 0.008 (2) | 0.006 (2) |
C4 | 0.038 (2) | 0.044 (2) | 0.058 (3) | −0.005 (2) | −0.004 (2) | 0.010 (2) |
C5 | 0.037 (2) | 0.033 (2) | 0.041 (2) | −0.011 (2) | −0.001 (2) | 0.004 (2) |
C6 | 0.038 (2) | 0.032 (2) | 0.032 (2) | −0.007 (2) | 0.001 (2) | 0.002 (2) |
C7 | 0.040 (2) | 0.033 (2) | 0.035 (2) | −0.004 (2) | 0.004 (2) | 0.001 (1) |
C8 | 0.054 (2) | 0.038 (2) | 0.042 (2) | 0.001 (2) | 0.001 (2) | −0.010 (2) |
C9 | 0.064 (3) | 0.046 (2) | 0.040 (2) | −0.005 (2) | −0.006 (2) | −0.017 (2) |
C10 | 0.077 (3) | 0.076 (4) | 0.052 (3) | −0.006 (3) | −0.026 (3) | −0.004 (3) |
C11 | 0.043 (2) | 0.038 (2) | 0.034 (2) | 0.005 (2) | −0.001 (2) | −0.001 (2) |
C12 | 0.034 (2) | 0.036 (2) | 0.032 (2) | 0.007 (2) | 0.000 (2) | 0.004 (2) |
C13 | 0.053 (3) | 0.045 (2) | 0.028 (2) | −0.007 (2) | −0.001 (2) | −0.003 (2) |
C14 | 0.049 (3) | 0.058 (3) | 0.042 (3) | 0.002 (2) | 0.013 (2) | 0.000 (2) |
C15 | 0.046 (3) | 0.064 (3) | 0.062 (3) | 0.007 (2) | 0.008 (2) | −0.016 (2) |
C16 | 0.047 (3) | 0.047 (3) | 0.057 (3) | 0.014 (2) | −0.009 (2) | −0.003 (2) |
C17 | 0.068 (3) | 0.057 (3) | 0.028 (2) | 0.004 (2) | −0.004 (2) | 0.005 (2) |
C18 | 0.051 (3) | 0.047 (2) | 0.045 (3) | −0.003 (2) | −0.001 (2) | −0.008 (2) |
C19 | 0.044 (2) | 0.049 (3) | 0.061 (3) | −0.008 (2) | 0.002 (2) | −0.002 (2) |
C20 | 0.065 (3) | 0.049 (3) | 0.088 (4) | 0.000 (3) | 0.017 (3) | 0.010 (3) |
C21 | 0.145 (8) | 0.116 (6) | 0.136 (7) | 0.057 (6) | 0.057 (6) | 0.059 (6) |
Geometric parameters (Å, º) top
O1—C11 | 1.411 (5) | C11—C12 | 1.531 (6) |
O1—H11 | 0.953 | C11—H10 | 0.973 |
N1—C5 | 1.376 (6) | C12—C13 | 1.536 (6) |
N1—C9 | 1.332 (6) | C12—H12 | 0.956 |
N1—C10 | 1.476 (7) | C13—C14 | 1.520 (7) |
N2—C12 | 1.547 (5) | C13—H13 | 0.939 |
N2—C16 | 1.529 (6) | C13—H14 | 0.976 |
N2—C17 | 1.497 (6) | C14—C15 | 1.530 (7) |
N2—C18 | 1.501 (6) | C14—C19 | 1.530 (7) |
C1—C2 | 1.347 (6) | C14—H15 | 0.959 |
C1—C6 | 1.423 (5) | C15—C16 | 1.524 (7) |
C1—H1 | 0.954 | C15—H16 | 0.960 |
C2—C3 | 1.406 (6) | C15—H17 | 0.966 |
C2—H2 | 0.965 | C16—H18 | 0.961 |
C3—C4 | 1.362 (7) | C16—H19 | 0.958 |
C3—H3 | 0.958 | C17—H20 | 0.955 |
C4—C5 | 1.410 (6) | C17—H21 | 0.952 |
C4—H4 | 0.964 | C17—H22 | 0.945 |
C5—C6 | 1.415 (6) | C18—C19 | 1.544 (7) |
C6—C7 | 1.421 (5) | C18—H23 | 0.965 |
C7—C8 | 1.373 (5) | C18—H24 | 0.951 |
C7—C11 | 1.527 (6) | C19—C20 | 1.497 (7) |
C8—C9 | 1.373 (6) | C19—H25 | 0.972 |
C8—H5 | 0.969 | C20—C21 | 1.22 (1) |
C9—H6 | 0.962 | C20—H26 | 0.968 |
C10—H7 | 0.960 | C21—H27 | 0.962 |
C10—H8 | 0.960 | C21—H28 | 0.965 |
C10—H9 | 0.960 | | |
| | | |
I2···O1i | 3.461 (3) | O1···C2ii | 3.200 (5) |
O1···C3ii | 3.151 (5) | O1···C4ii | 3.545 (5) |
| | | |
C11—O1—H11 | 109.0 | C11—C12—C13 | 114.5 (3) |
C5—N1—C9 | 120.7 (4) | C11—C12—H12 | 106.5 |
C5—N1—C10 | 119.7 (4) | C13—C12—H12 | 108.1 |
C9—N1—C10 | 119.6 (4) | C12—C13—C14 | 109.8 (3) |
C12—N2—C16 | 111.5 (3) | C12—C13—H13 | 109.7 |
C12—N2—C17 | 113.3 (3) | C12—C13—H14 | 107.7 |
C12—N2—C18 | 105.6 (3) | C14—C13—H13 | 111.3 |
C16—N2—C17 | 108.6 (3) | C14—C13—H14 | 110.0 |
C16—N2—C18 | 108.4 (3) | H13—C13—H14 | 108.2 |
C17—N2—C18 | 109.2 (3) | C13—C14—C15 | 107.6 (4) |
C2—C1—C6 | 121.3 (4) | C13—C14—C19 | 110.3 (4) |
C2—C1—H1 | 119.1 | C13—C14—H15 | 111.1 |
C6—C1—H1 | 119.6 | C15—C14—C19 | 108.0 (4) |
C1—C2—C3 | 120.4 (4) | C15—C14—H15 | 111.5 |
C1—C2—H2 | 119.2 | C19—C14—H15 | 108.3 |
C3—C2—H2 | 120.4 | C14—C15—C16 | 109.2 (4) |
C2—C3—C4 | 121.0 (4) | C14—C15—H16 | 110.2 |
C2—C3—H3 | 119.5 | C14—C15—H17 | 110.6 |
C4—C3—H3 | 119.5 | C16—C15—H16 | 110.0 |
C3—C4—C5 | 119.3 (4) | C16—C15—H17 | 109.5 |
C3—C4—H4 | 119.9 | H16—C15—H17 | 107.3 |
C5—C4—H4 | 120.8 | N2—C16—C15 | 109.3 (4) |
N1—C5—C4 | 120.7 (4) | N2—C16—H18 | 108.6 |
N1—C5—C6 | 118.7 (4) | N2—C16—H19 | 108.7 |
C4—C5—C6 | 120.5 (4) | C15—C16—H18 | 110.7 |
C1—C6—C5 | 117.4 (4) | C15—C16—H19 | 111.5 |
C1—C6—C7 | 123.0 (3) | H18—C16—H19 | 107.9 |
C5—C6—C7 | 119.6 (3) | N2—C17—H20 | 109.2 |
C6—C7—C8 | 118.4 (4) | N2—C17—H21 | 109.8 |
C6—C7—C11 | 122.1 (3) | N2—C17—H22 | 109.8 |
C8—C7—C11 | 119.5 (4) | H20—C17—H21 | 108.8 |
C7—C8—C9 | 120.1 (4) | H20—C17—H22 | 109.5 |
C7—C8—H5 | 118.3 | H21—C17—H22 | 109.7 |
C9—C8—H5 | 121.6 | N2—C18—C19 | 111.2 (4) |
N1—C9—C8 | 122.5 (4) | N2—C18—H23 | 108.5 |
N1—C9—H6 | 117.9 | N2—C18—H24 | 109.2 |
C8—C9—H6 | 119.7 | C19—C18—H23 | 109.8 |
N1—C10—H7 | 109.5 | C19—C18—H24 | 110.0 |
N1—C10—H8 | 109.5 | H23—C18—H24 | 108.1 |
N1—C10—H9 | 109.5 | C14—C19—C18 | 107.3 (4) |
H7—C10—H8 | 109.5 | C14—C19—C20 | 114.0 (4) |
H7—C10—H9 | 109.5 | C14—C19—H25 | 107.0 |
H8—C10—H9 | 109.5 | C18—C19—C20 | 113.3 (4) |
O1—C11—C7 | 110.5 (3) | C18—C19—H25 | 105.5 |
O1—C11—C12 | 110.8 (3) | C20—C19—H25 | 109.2 |
O1—C11—H10 | 108.0 | C19—C20—C21 | 127.8 (7) |
C7—C11—C12 | 108.4 (3) | C19—C20—H26 | 117.4 |
C7—C11—H10 | 110.1 | C21—C20—H26 | 114.6 |
C12—C11—H10 | 109.0 | C20—C21—H27 | 120.2 |
N2—C12—C11 | 114.0 (3) | C20—C21—H28 | 122.0 |
N2—C12—C13 | 106.6 (3) | H27—C21—H28 | 117.3 |
N2—C12—H12 | 106.8 | | |
| | | |
O1—C11—C7—C6 | 160.0 (3) | C6—C7—C8—C9 | 2.0 (6) |
O1—C11—C7—C8 | −19.2 (5) | C6—C7—C11—C12 | −78.4 (4) |
O1—C11—C12—N2 | −58.5 (4) | C7—C11—C12—C13 | −56.9 (4) |
O1—C11—C12—C13 | 64.6 (4) | C8—C7—C11—C12 | 102.3 (4) |
N1—C5—C4—C3 | 178.8 (4) | C8—C9—N1—C10 | 177.1 (4) |
N1—C5—C6—C1 | 179.6 (4) | C9—C8—C7—C11 | −178.7 (4) |
N1—C5—C6—C7 | −2.5 (6) | C11—C12—N2—C16 | 84.2 (4) |
N1—C9—C8—C7 | −1.5 (7) | C11—C12—N2—C17 | −38.7 (4) |
N2—C12—C11—C7 | −179.9 (3) | C11—C12—N2—C18 | −158.2 (3) |
N2—C12—C13—C14 | −24.2 (4) | C11—C12—C13—C14 | −151.1 (4) |
N2—C16—C15—C14 | −17.2 (5) | C12—N2—C16—C15 | 67.5 (4) |
N2—C18—C19—C14 | −14.9 (5) | C12—N2—C18—C19 | −51.8 (4) |
N2—C18—C19—C20 | 111.8 (4) | C12—C13—C14—C15 | 73.8 (5) |
C1—C2—C3—C4 | −1.9 (7) | C12—C13—C14—C19 | −43.8 (5) |
C1—C6—C5—C4 | −0.9 (6) | C13—C12—N2—C16 | −43.0 (4) |
C1—C6—C7—C8 | 177.7 (4) | C13—C12—N2—C17 | −165.9 (3) |
C1—C6—C7—C11 | −1.5 (6) | C13—C12—N2—C18 | 74.5 (4) |
C2—C1—C6—C5 | 1.2 (6) | C13—C14—C15—C16 | −48.6 (5) |
C2—C1—C6—C7 | −176.7 (4) | C13—C14—C19—C18 | 66.2 (5) |
C2—C3—C4—C5 | 2.1 (7) | C13—C14—C19—C20 | −60.1 (5) |
C3—C2—C1—C6 | 0.2 (6) | C14—C19—C20—C21 | −70.8 (9) |
C3—C4—C5—C6 | −0.7 (6) | C15—C14—C19—C18 | −51.2 (5) |
C4—C5—N1—C9 | −176.4 (4) | C15—C14—C19—C20 | −177.4 (4) |
C4—C5—N1—C10 | 5.4 (6) | C15—C16—N2—C17 | −167.0 (4) |
C4—C5—C6—C7 | 177.0 (4) | C15—C16—N2—C18 | −48.4 (5) |
C5—N1—C9—C8 | −1.1 (7) | C16—N2—C18—C19 | 67.8 (4) |
C5—C6—C7—C8 | 0.0 (6) | C16—C15—C14—C19 | 70.5 (5) |
C5—C6—C7—C11 | −179.3 (4) | C17—N2—C18—C19 | −174.0 (4) |
C6—C5—N1—C9 | 3.1 (6) | C18—C19—C20—C21 | 166.1 (8) |
C6—C5—N1—C10 | −175.1 (4) | C18—C19—C20—C21 | 166.1 (8) |
Symmetry codes: (i) −x−1, y+1/2, −z−1/2; (ii) −x−1, y−1/2, −z−1/2. |