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organic compounds
Arising from a hydrogen bond between the OH group of one molecule and the quinuclidine N atom of an adjacent molecule, molecules of the title compound, C19H24N2O, [also known as (3R,8S,9R)-10,11-dihydrocinchonidine] are linked [ON = 2.749 (4) Å] into a helical chain that runs along the shortest axis of the orthorhombic unit cell. The compound is isostructural with cinchonidine (which has a vinyl group instead of the ethyl group), whose structure has been described in detail [Oleksyn (1982). Acta Cryst. B38, 1832–1834].
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804034117/bt6573sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804034117/bt6573Isup2.hkl |
CCDC reference: 263662
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.007 Å
- R factor = 0.072
- wR factor = 0.160
- Data-to-parameter ratio = 8.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
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 25.00 From the CIF: _reflns_number_total 1663 Count of symmetry unique reflns 1663 Completeness (_total/calc) 100.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: atomic coordinates taken from isostructural cinchonidine (Oleksyn, 1982); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
(3R,8S,9R)-10,11-Dihydrocinchonidine top
Crystal data top
C19H24N2O | F(000) = 640 |
Mr = 296.40 | Dx = 1.217 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1148 reflections |
a = 10.518 (1) Å | θ = 2.1–18.5° |
b = 20.610 (2) Å | µ = 0.08 mm−1 |
c = 7.4612 (8) Å | T = 295 K |
V = 1617.4 (3) Å3 | Rod, colorless |
Z = 4 | 0.39 × 0.14 × 0.13 mm |
Data collection top
Bruker APEX area-detector diffractometer | 1533 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.050 |
Graphite monochromator | θmax = 25.0°, θmin = 2.0° |
φ and ω scans | h = −11→12 |
8440 measured reflections | k = −17→24 |
1663 independent reflections | l = −8→8 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.072 | H-atom parameters constrained |
wR(F2) = 0.160 | w = 1/[σ2(Fo2) + (0.0633P)2 + 0.5083P] where P = (Fo2 + 2Fc2)/3 |
S = 1.29 | (Δ/σ)max = 0.001 |
1663 reflections | Δρmax = 0.21 e Å−3 |
200 parameters | Δρmin = −0.15 e Å−3 |
0 restraints | Absolute structure: the calculation of the Flack parameter was suppressed. |
Primary atom site location: structure-invariant direct methods |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.8353 (3) | 0.5267 (1) | 1.0757 (4) | 0.046 (1) | |
N1 | 0.8003 (3) | 0.5798 (2) | 0.6889 (5) | 0.035 (1) | |
N2 | 1.2627 (4) | 0.4156 (2) | 1.0388 (7) | 0.054 (1) | |
C1 | 0.8341 (4) | 0.6299 (2) | 0.5573 (6) | 0.041 (1) | |
C2 | 0.8673 (4) | 0.6955 (2) | 0.6483 (7) | 0.042 (1) | |
C3 | 0.8838 (4) | 0.6812 (2) | 0.8494 (6) | 0.041 (1) | |
C4 | 0.7531 (4) | 0.6624 (2) | 0.9243 (7) | 0.047 (1) | |
C5 | 0.7023 (4) | 0.6070 (2) | 0.8085 (6) | 0.041 (1) | |
C6 | 0.9740 (4) | 0.6242 (2) | 0.8785 (6) | 0.041 (1) | |
C7 | 0.9176 (4) | 0.5631 (2) | 0.7890 (6) | 0.034 (1) | |
C8 | 0.8972 (4) | 0.5056 (2) | 0.9180 (6) | 0.035 (1) | |
C9 | 0.9785 (5) | 0.7300 (3) | 0.5605 (7) | 0.056 (1) | |
C10 | 0.9500 (7) | 0.7514 (3) | 0.3696 (8) | 0.082 (2) | |
C11 | 1.2025 (5) | 0.4536 (2) | 1.1512 (8) | 0.056 (1) | |
C12 | 1.0839 (5) | 0.4830 (2) | 1.1198 (7) | 0.045 (1) | |
C13 | 1.0229 (4) | 0.4728 (2) | 0.9615 (6) | 0.035 (1) | |
C14 | 1.0827 (4) | 0.4308 (2) | 0.8346 (6) | 0.037 (1) | |
C15 | 1.0306 (4) | 0.4137 (2) | 0.6674 (6) | 0.042 (1) | |
C16 | 1.0919 (5) | 0.3747 (2) | 0.5509 (7) | 0.051 (1) | |
C17 | 1.2117 (5) | 0.3495 (2) | 0.5933 (8) | 0.054 (1) | |
C18 | 1.2652 (4) | 0.3638 (2) | 0.7545 (8) | 0.052 (1) | |
C19 | 1.2035 (4) | 0.4040 (2) | 0.8806 (7) | 0.045 (1) | |
H1o | 0.7917 | 0.4956 | 1.1191 | 0.056* | |
H1a | 0.7633 | 0.6363 | 0.4758 | 0.049* | |
H1b | 0.9064 | 0.6152 | 0.4876 | 0.049* | |
H2 | 0.7929 | 0.7237 | 0.6359 | 0.051* | |
H3 | 0.9160 | 0.7197 | 0.9113 | 0.049* | |
H4a | 0.7608 | 0.6485 | 1.0480 | 0.057* | |
H4b | 0.6958 | 0.6992 | 0.9195 | 0.057* | |
H5a | 0.6702 | 0.5728 | 0.8858 | 0.050* | |
H5b | 0.6319 | 0.6228 | 0.7367 | 0.050* | |
H6a | 0.9854 | 0.6166 | 1.0058 | 0.049* | |
H6b | 1.0564 | 0.6339 | 0.8267 | 0.049* | |
H7 | 0.9799 | 0.5487 | 0.6997 | 0.041* | |
H8 | 0.8423 | 0.4738 | 0.8584 | 0.042* | |
H9a | 1.0514 | 0.7011 | 0.5594 | 0.067* | |
H9b | 1.0007 | 0.7677 | 0.6315 | 0.067* | |
H10a | 1.0235 | 0.7724 | 0.3200 | 0.123* | |
H10b | 0.8797 | 0.7811 | 0.3701 | 0.123* | |
H10c | 0.9288 | 0.7142 | 0.2983 | 0.123* | |
H11 | 1.2414 | 0.4618 | 1.2608 | 0.067* | |
H12 | 1.0474 | 0.5094 | 1.2069 | 0.054* | |
H15 | 0.9511 | 0.4300 | 0.6362 | 0.050* | |
H16 | 1.0542 | 0.3645 | 0.4417 | 0.061* | |
H17 | 1.2545 | 0.3232 | 0.5118 | 0.065* | |
H18 | 1.3445 | 0.3466 | 0.7824 | 0.062* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.056 (2) | 0.039 (2) | 0.044 (2) | −0.004 (2) | 0.018 (2) | 0.006 (2) |
N1 | 0.033 (2) | 0.035 (2) | 0.037 (2) | −0.002 (2) | 0.000 (2) | 0.000 (2) |
N2 | 0.045 (2) | 0.051 (3) | 0.067 (3) | 0.002 (2) | −0.022 (2) | 0.009 (2) |
C1 | 0.043 (3) | 0.039 (2) | 0.040 (3) | 0.003 (2) | −0.006 (2) | 0.004 (2) |
C2 | 0.044 (3) | 0.033 (2) | 0.050 (3) | 0.004 (2) | 0.004 (2) | 0.003 (2) |
C3 | 0.050 (3) | 0.029 (2) | 0.043 (3) | −0.008 (2) | −0.001 (2) | −0.003 (2) |
C4 | 0.053 (3) | 0.045 (3) | 0.044 (3) | 0.005 (2) | 0.011 (3) | −0.005 (2) |
C5 | 0.033 (2) | 0.041 (2) | 0.049 (3) | 0.000 (2) | −0.005 (2) | 0.003 (2) |
C6 | 0.038 (2) | 0.042 (2) | 0.041 (3) | −0.010 (2) | −0.001 (2) | 0.003 (2) |
C7 | 0.030 (2) | 0.034 (2) | 0.039 (2) | 0.001 (2) | 0.003 (2) | −0.004 (2) |
C8 | 0.033 (2) | 0.032 (2) | 0.039 (3) | −0.004 (2) | 0.002 (2) | −0.003 (2) |
C9 | 0.054 (3) | 0.048 (3) | 0.066 (4) | −0.006 (3) | 0.012 (3) | 0.003 (3) |
C10 | 0.097 (5) | 0.070 (4) | 0.079 (5) | 0.010 (4) | 0.023 (4) | 0.028 (4) |
C11 | 0.060 (3) | 0.052 (3) | 0.055 (3) | −0.012 (3) | −0.027 (3) | 0.005 (3) |
C12 | 0.051 (3) | 0.040 (2) | 0.045 (3) | −0.010 (2) | −0.003 (2) | 0.002 (2) |
C13 | 0.037 (2) | 0.028 (2) | 0.038 (2) | −0.006 (2) | −0.002 (2) | 0.008 (2) |
C14 | 0.033 (2) | 0.030 (2) | 0.046 (3) | −0.005 (2) | −0.003 (2) | 0.010 (2) |
C15 | 0.039 (2) | 0.040 (3) | 0.046 (3) | 0.006 (2) | −0.004 (2) | 0.001 (2) |
C16 | 0.055 (3) | 0.047 (3) | 0.050 (3) | 0.006 (3) | 0.007 (3) | −0.003 (3) |
C17 | 0.054 (3) | 0.044 (3) | 0.064 (4) | 0.001 (3) | 0.022 (3) | −0.003 (3) |
C18 | 0.035 (2) | 0.035 (3) | 0.086 (4) | 0.005 (2) | 0.002 (3) | 0.013 (3) |
C19 | 0.039 (2) | 0.033 (2) | 0.064 (3) | −0.004 (2) | 0.002 (2) | 0.013 (2) |
Geometric parameters (Å, º) top
O1—C8 | 1.413 (5) | O1—H1o | 0.85 |
N1—C1 | 1.469 (5) | C1—H1a | 0.97 |
N1—C5 | 1.474 (5) | C1—H1b | 0.97 |
N1—C7 | 1.483 (5) | C2—H2 | 0.98 |
N2—C11 | 1.311 (7) | C3—H3 | 0.98 |
N2—C19 | 1.356 (7) | C4—H4a | 0.97 |
C1—C2 | 1.552 (6) | C4—H4b | 0.97 |
C2—C9 | 1.517 (6) | C5—H5a | 0.97 |
C2—C3 | 1.539 (7) | C5—H5b | 0.97 |
C3—C6 | 1.525 (6) | C6—H6a | 0.97 |
C3—C4 | 1.533 (6) | C6—H6b | 0.97 |
C4—C5 | 1.529 (6) | C7—H7 | 0.98 |
C6—C7 | 1.544 (6) | C8—H8 | 0.98 |
C7—C8 | 1.542 (6) | C9—H9a | 0.97 |
C8—C13 | 1.520 (6) | C9—H9b | 0.97 |
C9—C10 | 1.521 (7) | C10—H10a | 0.96 |
C11—C12 | 1.407 (7) | C10—H10b | 0.96 |
C12—C13 | 1.361 (6) | C10—H10c | 0.96 |
C13—C14 | 1.428 (6) | C11—H11 | 0.93 |
C14—C15 | 1.407 (6) | C12—H12 | 0.93 |
C14—C19 | 1.427 (6) | C15—H15 | 0.93 |
C15—C16 | 1.348 (6) | C16—H16 | 0.93 |
C16—C17 | 1.400 (7) | C17—H17 | 0.93 |
C17—C18 | 1.360 (7) | C18—H18 | 0.93 |
C18—C19 | 1.411 (7) | ||
C1—N1—C5 | 107.8 (3) | C4—C3—H3 | 110.0 |
C1—N1—C7 | 107.4 (3) | C2—C3—H3 | 110.0 |
C5—N1—C7 | 111.4 (3) | C5—C4—H4a | 110.3 |
C11—N2—C19 | 116.1 (4) | C3—C4—H4a | 110.3 |
N1—C1—C2 | 112.0 (4) | C5—C4—H4b | 110.3 |
C1—C2—C3 | 106.6 (4) | C3—C4—H4b | 110.3 |
C1—C2—C9 | 113.1 (4) | H4a—C4—H4b | 108.5 |
C3—C2—C9 | 115.1 (4) | N1—C5—H5a | 109.1 |
C2—C3—C4 | 107.6 (4) | C4—C5—H5a | 109.1 |
C2—C3—C6 | 110.9 (4) | N1—C5—H5b | 109.1 |
C4—C3—C6 | 108.2 (4) | C4—C5—H5b | 109.1 |
C5—C4—C3 | 107.2 (4) | H5a—C5—H5b | 107.9 |
N1—C5—C4 | 112.4 (3) | C3—C6—H6a | 109.9 |
C3—C6—C7 | 109.1 (3) | C7—C6—H6a | 109.9 |
N1—C7—C6 | 110.4 (3) | C3—C6—H6b | 109.9 |
N1—C7—C8 | 112.1 (3) | C7—C6—H6b | 109.9 |
C6—C7—C8 | 114.2 (4) | H6a—C6—H6b | 108.3 |
O1—C8—C7 | 110.4 (3) | N1—C7—H7 | 106.5 |
O1—C8—C13 | 111.1 (4) | C8—C7—H7 | 106.5 |
C7—C8—C13 | 110.7 (3) | C6—C7—H7 | 106.5 |
C2—C9—C10 | 112.9 (5) | O1—C8—H8 | 108.2 |
N2—C11—C12 | 125.4 (5) | C13—C8—H8 | 108.2 |
C11—C12—C13 | 119.7 (5) | C7—C8—H8 | 108.2 |
C12—C13—C14 | 117.5 (4) | C2—C9—H9a | 109.0 |
C8—C13—C12 | 121.8 (4) | C10—C9—H9a | 109.0 |
C8—C13—C14 | 120.7 (4) | C2—C9—H9b | 109.0 |
C13—C14—C15 | 124.6 (4) | C10—C9—H9b | 109.0 |
C13—C14—C19 | 117.9 (4) | H9a—C9—H9b | 107.8 |
C15—C14—C19 | 117.5 (4) | C9—C10—H10a | 109.5 |
C14—C15—C16 | 122.3 (5) | C9—C10—H10b | 109.5 |
C15—C16—C17 | 120.4 (5) | H10a—C10—H10b | 109.5 |
C16—C17—C18 | 119.5 (5) | C9—C10—H10c | 109.5 |
C17—C18—C19 | 121.8 (5) | H10a—C10—H10c | 109.5 |
N2—C19—C14 | 123.3 (5) | H10b—C10—H10c | 109.5 |
N2—C19—C18 | 118.2 (4) | N2—C11—H11 | 117.3 |
C14—C19—C18 | 118.5 (5) | C12—C11—H11 | 117.3 |
C8—O1—H1o | 109.5 | C13—C12—H12 | 120.1 |
N1—C1—H1a | 109.2 | C11—C12—H12 | 120.1 |
C2—C1—H1a | 109.2 | C16—C15—H15 | 118.8 |
N1—C1—H1b | 109.2 | C14—C15—H15 | 118.8 |
C2—C1—H1b | 109.2 | C15—C16—H16 | 119.8 |
H1a—C1—H1b | 107.9 | C17—C16—H16 | 119.8 |
C9—C2—H2 | 107.2 | C18—C17—H17 | 120.3 |
C3—C2—H2 | 107.2 | C16—C17—H17 | 120.3 |
C1—C2—H2 | 107.2 | C17—C18—H18 | 119.1 |
C6—C3—H3 | 110.0 | C19—C18—H18 | 119.1 |
C5—N1—C1—C2 | 51.2 (5) | C1—C2—C9—C10 | 65.3 (5) |
C7—N1—C1—C2 | −69.0 (4) | C19—N2—C11—C12 | −0.5 (7) |
N1—C1—C2—C9 | 140.5 (4) | N2—C11—C12—C13 | −0.2 (7) |
N1—C1—C2—C3 | 13.0 (5) | C11—C12—C13—C14 | 1.3 (6) |
C9—C2—C3—C6 | −75.7 (5) | C11—C12—C13—C8 | −177.5 (4) |
C1—C2—C3—C6 | 50.5 (5) | O1—C8—C13—C12 | −20.6 (5) |
C9—C2—C3—C4 | 166.2 (4) | C7—C8—C13—C12 | 102.4 (5) |
C1—C2—C3—C4 | −67.6 (4) | O1—C8—C13—C14 | 160.7 (3) |
C6—C3—C4—C5 | −66.0 (5) | C7—C8—C13—C14 | −76.3 (5) |
C2—C3—C4—C5 | 53.9 (5) | C12—C13—C14—C15 | 178.1 (4) |
C1—N1—C5—C4 | −66.6 (5) | C8—C13—C14—C15 | −3.1 (6) |
C7—N1—C5—C4 | 51.0 (5) | C12—C13—C14—C19 | −1.7 (6) |
C3—C4—C5—N1 | 11.7 (5) | C8—C13—C14—C19 | 177.2 (4) |
C4—C3—C6—C7 | 56.6 (5) | C19—C14—C15—C16 | −1.4 (6) |
C2—C3—C6—C7 | −61.2 (5) | C13—C14—C15—C16 | 178.9 (4) |
C1—N1—C7—C8 | −174.0 (3) | C14—C15—C16—C17 | −0.1 (7) |
C5—N1—C7—C8 | 68.1 (4) | C15—C16—C17—C18 | 1.1 (7) |
C1—N1—C7—C6 | 57.5 (4) | C16—C17—C18—C19 | −0.5 (7) |
C5—N1—C7—C6 | −60.4 (4) | C11—N2—C19—C18 | 179.4 (4) |
C3—C6—C7—N1 | 5.2 (5) | C11—N2—C19—C14 | 0.0 (7) |
C3—C6—C7—C8 | −122.2 (4) | C17—C18—C19—N2 | 179.6 (4) |
N1—C7—C8—O1 | −78.9 (4) | C17—C18—C19—C14 | −1.0 (7) |
C6—C7—C8—O1 | 47.6 (5) | C15—C14—C19—N2 | −178.7 (4) |
N1—C7—C8—C13 | 157.7 (3) | C13—C14—C19—N2 | 1.1 (6) |
C6—C7—C8—C13 | −75.8 (5) | C15—C14—C19—C18 | 1.9 (6) |
C3—C2—C9—C10 | −171.9 (4) | C13—C14—C19—C18 | −178.3 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1o···N1i | 0.85 | 1.90 | 2.749 (4) | 173 |
Symmetry code: (i) −x+3/2, −y+1, z+1/2. |
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