organic compounds
2,4-Bis(2-ethoxyphenyl)-3-azabicyclo[3.3.1]nonan-9-one
aDepartment of Biomedicinal Chemistry, Inje University, Gimhae, Gyeongnam 621 749, Republic of Korea, and bDepartment of Chemistry, IIT Madras, Chennai 600 036, TamilNadu, India
*Correspondence e-mail: parthisivam@yahoo.co.in
The 24H29NO3, contains two independent molecules, which each exibit a twin-chair conformation with an equatorial orientation of the ortho-ethoxyphenyl groups but different dihedral angles [41.3 (1) and 24.1 (1)°] between the benzene rings. In the crystal, pairs of weak C—H⋯O hydrogen bonds link the two different independent molecules into dimers.
of the title compound, CRelated literature
For the synthesis and stereochemistry of 3-azabicyclo[3.3.1]nonan-9-ones, see: Park et al. (2011) and for their biological properties, see: Jeyaraman & Avila (1981); Park et al. (2012a); Parthiban et al. (2010a,b; 2011a). For similar structures, see: Park et al. (2012b); Parthiban et al. (2009a,b; 2011b). For see: Kalsi (1997); Cremer & Pople (1975).
Experimental
Crystal data
|
Refinement
|
|
Data collection: APEX2 (Bruker, 2004); cell SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536812044856/cv5345sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812044856/cv5345Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812044856/cv5345Isup3.cml
The 2,4-bis(2-ethoxyphenyl)-3-azabicyclo[3.3.1]nonan-9-one was synthesized by a modified and an optimized double Mannich condensation in one-pot, using 2-ethoxybenzaldehyde (0.1 mol, 15.018 g/13.94 ml), cyclohexanone (0.05 mol, 4.90 g/5.18 ml) and ammonium acetate (0.075 mol, 5.78 g) in a 50 ml of absolute ethanol (Park et al., 2011). The mixture was gently warmed on a hot plate at 303–308 K (30–35° C) with moderate stirring till the complete consumption of the starting materials, which was monitored by TLC. After completion of the rection, the crude compound was separated by filtration and gently washed with 1:5 cold ethanol-ether mixture. X-ray diffraction quality crystals of the title compound were obtained by slow evaporation from ethanol.
All hydrogen atoms were fixed geometrically and allowed to ride on the parent carbon atoms, with C—H = 0.93–0.98 Å and N—H = 0.86 Å, and with Uiso(H) = 1.2–1.5Ueq of the parent atom.
Data collection: APEX2 (Bruker, 2004); cell
SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. Two independent molecules of the title compound with atomic labels and displacement ellipsoids represented with 30% probability level. H atoms omitted for clarity. |
C24H29NO3 | Z = 4 |
Mr = 379.49 | F(000) = 816 |
Triclinic, P1 | Dx = 1.194 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.7981 (3) Å | Cell parameters from 5334 reflections |
b = 13.6139 (5) Å | θ = 0.0–0.0° |
c = 16.7098 (6) Å | µ = 0.08 mm−1 |
α = 74.363 (2)° | T = 298 K |
β = 80.464 (2)° | Block, colourless |
γ = 83.563 (2)° | 0.35 × 0.28 × 0.22 mm |
V = 2111.42 (13) Å3 |
Bruker APEXII CCD area-detector diffractometer | 9839 independent reflections |
Radiation source: fine-focus sealed tube | 6037 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
phi and ω scans | θmax = 28.6°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −12→12 |
Tmin = 0.973, Tmax = 0.983 | k = −17→18 |
27579 measured reflections | l = −21→22 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.150 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0546P)2 + 0.6801P] where P = (Fo2 + 2Fc2)/3 |
9839 reflections | (Δ/σ)max < 0.001 |
509 parameters | Δρmax = 0.53 e Å−3 |
0 restraints | Δρmin = −0.45 e Å−3 |
C24H29NO3 | γ = 83.563 (2)° |
Mr = 379.49 | V = 2111.42 (13) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.7981 (3) Å | Mo Kα radiation |
b = 13.6139 (5) Å | µ = 0.08 mm−1 |
c = 16.7098 (6) Å | T = 298 K |
α = 74.363 (2)° | 0.35 × 0.28 × 0.22 mm |
β = 80.464 (2)° |
Bruker APEXII CCD area-detector diffractometer | 9839 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 6037 reflections with I > 2σ(I) |
Tmin = 0.973, Tmax = 0.983 | Rint = 0.022 |
27579 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.150 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.53 e Å−3 |
9839 reflections | Δρmin = −0.45 e Å−3 |
509 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.36743 (18) | 0.85897 (14) | 0.06351 (11) | 0.0500 (4) | |
H1 | 0.4178 | 0.8488 | 0.0103 | 0.060* | |
C2 | 0.25640 (19) | 0.77992 (14) | 0.09612 (12) | 0.0533 (4) | |
H2 | 0.1937 | 0.7901 | 0.0541 | 0.064* | |
C3 | 0.1701 (2) | 0.78294 (16) | 0.18078 (13) | 0.0647 (5) | |
H3A | 0.1321 | 0.8526 | 0.1778 | 0.078* | |
H3B | 0.0927 | 0.7406 | 0.1902 | 0.078* | |
C4 | 0.2490 (2) | 0.74703 (17) | 0.25537 (13) | 0.0695 (6) | |
H4A | 0.3019 | 0.8022 | 0.2574 | 0.083* | |
H4B | 0.1828 | 0.7322 | 0.3063 | 0.083* | |
C5 | 0.3472 (2) | 0.65312 (15) | 0.25377 (13) | 0.0616 (5) | |
H5A | 0.2940 | 0.5931 | 0.2713 | 0.074* | |
H5B | 0.4107 | 0.6462 | 0.2941 | 0.074* | |
C6 | 0.4315 (2) | 0.65624 (14) | 0.16746 (12) | 0.0536 (5) | |
H6 | 0.4811 | 0.5892 | 0.1692 | 0.064* | |
C7 | 0.53772 (18) | 0.73929 (14) | 0.13630 (11) | 0.0488 (4) | |
H7 | 0.5881 | 0.7323 | 0.0821 | 0.059* | |
C8 | 0.3305 (2) | 0.67594 (15) | 0.10576 (13) | 0.0586 (5) | |
C9 | 0.29786 (19) | 0.96590 (14) | 0.04698 (13) | 0.0554 (5) | |
C10 | 0.2861 (2) | 1.02513 (16) | 0.10223 (16) | 0.0747 (6) | |
H10 | 0.3272 | 1.0012 | 0.1508 | 0.090* | |
C11 | 0.2138 (3) | 1.12062 (19) | 0.0872 (2) | 0.0993 (9) | |
H11 | 0.2060 | 1.1604 | 0.1253 | 0.119* | |
C12 | 0.1538 (3) | 1.15537 (18) | 0.0147 (2) | 0.0938 (9) | |
H12 | 0.1057 | 1.2194 | 0.0039 | 0.113* | |
C13 | 0.1635 (2) | 1.09799 (18) | −0.04144 (17) | 0.0791 (7) | |
H13 | 0.1215 | 1.1224 | −0.0897 | 0.095* | |
C14 | 0.2359 (2) | 1.00353 (16) | −0.02670 (14) | 0.0635 (5) | |
C15 | 0.1763 (3) | 0.9619 (2) | −0.14731 (16) | 0.0920 (8) | |
H15A | 0.2042 | 1.0245 | −0.1879 | 0.110* | |
H15B | 0.0777 | 0.9700 | −0.1282 | 0.110* | |
C16 | 0.2073 (4) | 0.8738 (3) | −0.1860 (2) | 0.1269 (12) | |
H16A | 0.3050 | 0.8670 | −0.2050 | 0.190* | |
H16B | 0.1571 | 0.8854 | −0.2327 | 0.190* | |
H16C | 0.1799 | 0.8123 | −0.1451 | 0.190* | |
C17 | 0.64188 (18) | 0.72424 (14) | 0.19648 (11) | 0.0486 (4) | |
C18 | 0.75334 (18) | 0.65048 (14) | 0.19377 (11) | 0.0505 (4) | |
C19 | 0.8500 (2) | 0.63614 (16) | 0.24840 (12) | 0.0581 (5) | |
H19 | 0.9245 | 0.5878 | 0.2460 | 0.070* | |
C20 | 0.8364 (2) | 0.69305 (18) | 0.30616 (13) | 0.0651 (6) | |
H20 | 0.9017 | 0.6828 | 0.3427 | 0.078* | |
C21 | 0.7274 (2) | 0.76473 (18) | 0.31044 (13) | 0.0671 (6) | |
H21 | 0.7179 | 0.8028 | 0.3499 | 0.081* | |
C22 | 0.6315 (2) | 0.77980 (16) | 0.25514 (12) | 0.0585 (5) | |
H22 | 0.5580 | 0.8289 | 0.2578 | 0.070* | |
C23 | 0.8671 (2) | 0.51955 (16) | 0.12899 (14) | 0.0691 (6) | |
H23A | 0.8744 | 0.4733 | 0.1838 | 0.083* | |
H23B | 0.9548 | 0.5504 | 0.1076 | 0.083* | |
C24 | 0.8344 (3) | 0.4629 (2) | 0.0709 (2) | 0.1067 (10) | |
H24A | 0.7482 | 0.4319 | 0.0930 | 0.160* | |
H24B | 0.9071 | 0.4108 | 0.0650 | 0.160* | |
H24C | 0.8267 | 0.5094 | 0.0170 | 0.160* | |
C1A | 0.64687 (16) | 0.15039 (12) | 0.44479 (10) | 0.0422 (4) | |
H1A | 0.6561 | 0.1204 | 0.3968 | 0.051* | |
C2A | 0.76566 (17) | 0.22198 (13) | 0.42932 (11) | 0.0473 (4) | |
H2A | 0.8545 | 0.1818 | 0.4231 | 0.057* | |
C3A | 0.7659 (2) | 0.27739 (14) | 0.49824 (12) | 0.0556 (5) | |
H3A1 | 0.7619 | 0.2270 | 0.5520 | 0.067* | |
H3A2 | 0.8529 | 0.3093 | 0.4883 | 0.067* | |
C4A | 0.6469 (2) | 0.35883 (15) | 0.50361 (12) | 0.0602 (5) | |
H4A1 | 0.6689 | 0.4024 | 0.5364 | 0.072* | |
H4A2 | 0.5636 | 0.3256 | 0.5329 | 0.072* | |
C5A | 0.6178 (2) | 0.42519 (14) | 0.41788 (13) | 0.0589 (5) | |
H5A1 | 0.6878 | 0.4745 | 0.3966 | 0.071* | |
H5A2 | 0.5285 | 0.4630 | 0.4247 | 0.071* | |
C6A | 0.61683 (18) | 0.36447 (13) | 0.35247 (11) | 0.0484 (4) | |
H6A | 0.6112 | 0.4128 | 0.2976 | 0.058* | |
C7A | 0.50066 (17) | 0.28949 (12) | 0.37073 (10) | 0.0426 (4) | |
H7A | 0.5136 | 0.2557 | 0.3248 | 0.051* | |
C8A | 0.75265 (18) | 0.30110 (14) | 0.34832 (12) | 0.0496 (4) | |
C9A | 0.65574 (18) | 0.06396 (12) | 0.52316 (11) | 0.0450 (4) | |
C10A | 0.5745 (2) | 0.06544 (14) | 0.59797 (12) | 0.0576 (5) | |
H10A | 0.5097 | 0.1203 | 0.6007 | 0.069* | |
C11A | 0.5869 (3) | −0.01343 (16) | 0.66985 (13) | 0.0712 (6) | |
H11A | 0.5304 | −0.0116 | 0.7200 | 0.085* | |
C12A | 0.6830 (3) | −0.09377 (15) | 0.66610 (15) | 0.0729 (6) | |
H12A | 0.6926 | −0.1461 | 0.7143 | 0.087* | |
C13A | 0.7656 (2) | −0.09789 (14) | 0.59183 (15) | 0.0638 (6) | |
H13A | 0.8301 | −0.1531 | 0.5898 | 0.077* | |
C14A | 0.75241 (19) | −0.01967 (12) | 0.52014 (12) | 0.0503 (4) | |
C15A | 0.9384 (2) | −0.09232 (16) | 0.43565 (16) | 0.0736 (7) | |
H15C | 0.9027 | −0.1594 | 0.4497 | 0.088* | |
H15D | 1.0042 | −0.0933 | 0.4734 | 0.088* | |
C16A | 1.0074 (3) | −0.0658 (2) | 0.34722 (17) | 0.0906 (8) | |
H16D | 0.9444 | −0.0723 | 0.3109 | 0.136* | |
H16E | 1.0885 | −0.1114 | 0.3413 | 0.136* | |
H16F | 1.0339 | 0.0033 | 0.3323 | 0.136* | |
C17A | 0.35634 (17) | 0.34232 (12) | 0.37438 (10) | 0.0419 (4) | |
C18A | 0.28975 (18) | 0.36874 (12) | 0.30268 (11) | 0.0451 (4) | |
C19A | 0.15377 (19) | 0.41012 (14) | 0.30671 (13) | 0.0563 (5) | |
H19A | 0.1086 | 0.4249 | 0.2596 | 0.068* | |
C20A | 0.0859 (2) | 0.42923 (15) | 0.37999 (14) | 0.0643 (6) | |
H20A | −0.0052 | 0.4574 | 0.3822 | 0.077* | |
C21A | 0.1504 (2) | 0.40738 (16) | 0.45031 (13) | 0.0637 (5) | |
H21A | 0.1046 | 0.4224 | 0.4995 | 0.076* | |
C22A | 0.28471 (19) | 0.36263 (14) | 0.44692 (12) | 0.0538 (5) | |
H22A | 0.3276 | 0.3459 | 0.4950 | 0.065* | |
C23A | 0.3037 (2) | 0.36747 (16) | 0.15767 (12) | 0.0666 (6) | |
H23C | 0.2675 | 0.4381 | 0.1408 | 0.080* | |
H23D | 0.2278 | 0.3237 | 0.1677 | 0.080* | |
C24A | 0.4124 (3) | 0.3436 (2) | 0.09121 (15) | 0.1005 (9) | |
H24D | 0.4836 | 0.3907 | 0.0790 | 0.151* | |
H24E | 0.3719 | 0.3496 | 0.0414 | 0.151* | |
H24F | 0.4520 | 0.2751 | 0.1102 | 0.151* | |
N1 | 0.46630 (15) | 0.84156 (11) | 0.12323 (9) | 0.0500 (4) | |
H1B | 0.4809 | 0.8864 | 0.1480 | 0.060* | |
N1A | 0.51362 (13) | 0.21006 (10) | 0.44872 (8) | 0.0422 (3) | |
H1A1 | 0.4502 | 0.1998 | 0.4917 | 0.051* | |
O1 | 0.3081 (2) | 0.61501 (12) | 0.06929 (11) | 0.0909 (5) | |
O2 | 0.25195 (18) | 0.94051 (14) | −0.07861 (10) | 0.0878 (5) | |
O3 | 0.75755 (14) | 0.59694 (11) | 0.13539 (9) | 0.0661 (4) | |
O1A | 0.84094 (15) | 0.31195 (12) | 0.28738 (9) | 0.0741 (4) | |
O2A | 0.82815 (14) | −0.01692 (10) | 0.44357 (9) | 0.0644 (4) | |
O3A | 0.36692 (14) | 0.35032 (10) | 0.23189 (8) | 0.0589 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0456 (10) | 0.0543 (10) | 0.0472 (10) | −0.0013 (8) | −0.0110 (8) | −0.0063 (8) |
C2 | 0.0506 (10) | 0.0540 (11) | 0.0582 (11) | −0.0054 (8) | −0.0189 (9) | −0.0116 (9) |
C3 | 0.0476 (11) | 0.0613 (12) | 0.0793 (15) | −0.0091 (9) | −0.0014 (10) | −0.0105 (11) |
C4 | 0.0655 (13) | 0.0780 (14) | 0.0604 (13) | −0.0117 (11) | 0.0062 (10) | −0.0165 (11) |
C5 | 0.0645 (12) | 0.0567 (11) | 0.0587 (12) | −0.0146 (10) | −0.0085 (10) | −0.0025 (9) |
C6 | 0.0604 (11) | 0.0431 (9) | 0.0590 (11) | 0.0024 (8) | −0.0152 (9) | −0.0143 (8) |
C7 | 0.0473 (10) | 0.0551 (10) | 0.0418 (9) | 0.0023 (8) | −0.0075 (8) | −0.0106 (8) |
C8 | 0.0666 (13) | 0.0530 (11) | 0.0600 (12) | −0.0098 (9) | −0.0135 (10) | −0.0162 (9) |
C9 | 0.0470 (10) | 0.0486 (10) | 0.0663 (12) | −0.0060 (8) | −0.0142 (9) | −0.0028 (9) |
C10 | 0.0813 (15) | 0.0523 (12) | 0.0957 (17) | −0.0022 (11) | −0.0362 (13) | −0.0146 (12) |
C11 | 0.116 (2) | 0.0553 (14) | 0.139 (3) | 0.0024 (14) | −0.049 (2) | −0.0305 (15) |
C12 | 0.0855 (18) | 0.0458 (12) | 0.140 (3) | 0.0024 (12) | −0.0352 (17) | 0.0019 (15) |
C13 | 0.0705 (15) | 0.0619 (14) | 0.0921 (18) | −0.0055 (11) | −0.0250 (13) | 0.0106 (13) |
C14 | 0.0512 (11) | 0.0592 (12) | 0.0702 (14) | −0.0024 (9) | −0.0175 (10) | 0.0052 (11) |
C15 | 0.0973 (19) | 0.0965 (19) | 0.0769 (16) | −0.0138 (15) | −0.0428 (14) | 0.0078 (14) |
C16 | 0.162 (3) | 0.133 (3) | 0.100 (2) | 0.015 (2) | −0.057 (2) | −0.041 (2) |
C17 | 0.0442 (10) | 0.0558 (10) | 0.0414 (9) | −0.0019 (8) | −0.0066 (7) | −0.0052 (8) |
C18 | 0.0470 (10) | 0.0554 (10) | 0.0417 (10) | −0.0013 (8) | −0.0052 (8) | −0.0015 (8) |
C19 | 0.0463 (10) | 0.0652 (12) | 0.0538 (11) | 0.0013 (9) | −0.0092 (9) | −0.0010 (10) |
C20 | 0.0511 (12) | 0.0883 (15) | 0.0521 (12) | −0.0092 (11) | −0.0147 (9) | −0.0056 (11) |
C21 | 0.0571 (12) | 0.0916 (16) | 0.0579 (12) | −0.0059 (11) | −0.0111 (10) | −0.0261 (11) |
C22 | 0.0492 (11) | 0.0708 (13) | 0.0559 (11) | −0.0002 (9) | −0.0092 (9) | −0.0172 (10) |
C23 | 0.0626 (13) | 0.0655 (13) | 0.0713 (14) | 0.0150 (10) | −0.0071 (11) | −0.0133 (11) |
C24 | 0.108 (2) | 0.103 (2) | 0.124 (2) | 0.0248 (17) | −0.0270 (19) | −0.0614 (19) |
C1A | 0.0416 (9) | 0.0383 (8) | 0.0458 (9) | 0.0075 (7) | −0.0142 (7) | −0.0083 (7) |
C2A | 0.0358 (9) | 0.0492 (10) | 0.0518 (10) | 0.0056 (7) | −0.0110 (7) | −0.0050 (8) |
C3A | 0.0541 (11) | 0.0552 (11) | 0.0580 (11) | −0.0090 (9) | −0.0212 (9) | −0.0052 (9) |
C4A | 0.0675 (13) | 0.0555 (11) | 0.0641 (13) | −0.0064 (10) | −0.0174 (10) | −0.0208 (10) |
C5A | 0.0560 (11) | 0.0425 (10) | 0.0771 (14) | −0.0019 (8) | −0.0147 (10) | −0.0108 (9) |
C6A | 0.0466 (10) | 0.0443 (9) | 0.0452 (10) | 0.0034 (8) | −0.0100 (8) | 0.0037 (8) |
C7A | 0.0428 (9) | 0.0427 (9) | 0.0412 (9) | 0.0071 (7) | −0.0144 (7) | −0.0079 (7) |
C8A | 0.0421 (10) | 0.0531 (10) | 0.0502 (11) | −0.0038 (8) | −0.0078 (8) | −0.0064 (8) |
C9A | 0.0457 (9) | 0.0381 (9) | 0.0504 (10) | 0.0002 (7) | −0.0169 (8) | −0.0054 (7) |
C10A | 0.0653 (12) | 0.0477 (10) | 0.0550 (12) | 0.0000 (9) | −0.0130 (10) | −0.0038 (9) |
C11A | 0.0909 (16) | 0.0619 (13) | 0.0550 (12) | −0.0117 (12) | −0.0132 (11) | −0.0008 (10) |
C12A | 0.1019 (18) | 0.0451 (11) | 0.0682 (15) | −0.0135 (12) | −0.0378 (13) | 0.0100 (10) |
C13A | 0.0768 (14) | 0.0348 (9) | 0.0820 (15) | 0.0025 (9) | −0.0395 (12) | −0.0045 (10) |
C14A | 0.0511 (10) | 0.0382 (9) | 0.0642 (12) | 0.0023 (8) | −0.0258 (9) | −0.0091 (8) |
C15A | 0.0755 (14) | 0.0576 (12) | 0.1014 (18) | 0.0314 (11) | −0.0464 (13) | −0.0378 (12) |
C16A | 0.0789 (16) | 0.105 (2) | 0.100 (2) | 0.0374 (15) | −0.0292 (15) | −0.0553 (16) |
C17A | 0.0396 (9) | 0.0363 (8) | 0.0480 (10) | 0.0039 (7) | −0.0129 (7) | −0.0064 (7) |
C18A | 0.0473 (10) | 0.0348 (8) | 0.0513 (10) | 0.0008 (7) | −0.0163 (8) | −0.0036 (7) |
C19A | 0.0483 (11) | 0.0501 (10) | 0.0670 (13) | 0.0043 (8) | −0.0256 (10) | −0.0016 (9) |
C20A | 0.0410 (10) | 0.0598 (12) | 0.0801 (15) | 0.0105 (9) | −0.0118 (10) | −0.0011 (11) |
C21A | 0.0517 (11) | 0.0672 (13) | 0.0613 (12) | 0.0137 (10) | −0.0016 (9) | −0.0089 (10) |
C22A | 0.0496 (10) | 0.0565 (11) | 0.0526 (11) | 0.0085 (9) | −0.0146 (9) | −0.0100 (9) |
C23A | 0.0905 (16) | 0.0575 (12) | 0.0560 (12) | 0.0004 (11) | −0.0338 (11) | −0.0100 (10) |
C24A | 0.122 (2) | 0.126 (2) | 0.0593 (15) | 0.0061 (19) | −0.0238 (15) | −0.0328 (15) |
N1 | 0.0488 (8) | 0.0465 (8) | 0.0555 (9) | −0.0023 (7) | −0.0180 (7) | −0.0085 (7) |
N1A | 0.0365 (7) | 0.0422 (7) | 0.0420 (8) | 0.0067 (6) | −0.0079 (6) | −0.0033 (6) |
O1 | 0.1271 (15) | 0.0672 (10) | 0.0981 (12) | −0.0053 (9) | −0.0477 (11) | −0.0361 (9) |
O2 | 0.0957 (12) | 0.1031 (13) | 0.0630 (10) | 0.0266 (10) | −0.0349 (9) | −0.0180 (9) |
O3 | 0.0636 (9) | 0.0718 (9) | 0.0633 (9) | 0.0197 (7) | −0.0188 (7) | −0.0218 (7) |
O1A | 0.0576 (8) | 0.0869 (11) | 0.0582 (9) | 0.0040 (8) | 0.0064 (7) | 0.0023 (8) |
O2A | 0.0614 (8) | 0.0535 (8) | 0.0740 (10) | 0.0239 (6) | −0.0188 (7) | −0.0146 (7) |
O3A | 0.0659 (8) | 0.0636 (8) | 0.0467 (7) | 0.0129 (7) | −0.0236 (6) | −0.0106 (6) |
C1—N1 | 1.460 (2) | C1A—C9A | 1.514 (2) |
C1—C9 | 1.511 (3) | C1A—C2A | 1.546 (2) |
C1—C2 | 1.545 (3) | C1A—H1A | 0.9800 |
C1—H1 | 0.9800 | C2A—C8A | 1.500 (2) |
C2—C8 | 1.497 (3) | C2A—C3A | 1.538 (3) |
C2—C3 | 1.531 (3) | C2A—H2A | 0.9800 |
C2—H2 | 0.9800 | C3A—C4A | 1.525 (3) |
C3—C4 | 1.516 (3) | C3A—H3A1 | 0.9700 |
C3—H3A | 0.9700 | C3A—H3A2 | 0.9700 |
C3—H3B | 0.9700 | C4A—C5A | 1.526 (3) |
C4—C5 | 1.515 (3) | C4A—H4A1 | 0.9700 |
C4—H4A | 0.9700 | C4A—H4A2 | 0.9700 |
C4—H4B | 0.9700 | C5A—C6A | 1.540 (3) |
C5—C6 | 1.531 (3) | C5A—H5A1 | 0.9700 |
C5—H5A | 0.9700 | C5A—H5A2 | 0.9700 |
C5—H5B | 0.9700 | C6A—C8A | 1.505 (2) |
C6—C8 | 1.498 (3) | C6A—C7A | 1.552 (2) |
C6—C7 | 1.549 (3) | C6A—H6A | 0.9800 |
C6—H6 | 0.9800 | C7A—N1A | 1.466 (2) |
C7—N1 | 1.464 (2) | C7A—C17A | 1.513 (2) |
C7—C17 | 1.509 (2) | C7A—H7A | 0.9800 |
C7—H7 | 0.9800 | C8A—O1A | 1.210 (2) |
C8—O1 | 1.210 (2) | C9A—C10A | 1.370 (3) |
C9—C10 | 1.364 (3) | C9A—C14A | 1.403 (2) |
C9—C14 | 1.409 (3) | C10A—C11A | 1.391 (3) |
C10—C11 | 1.390 (3) | C10A—H10A | 0.9300 |
C10—H10 | 0.9300 | C11A—C12A | 1.368 (3) |
C11—C12 | 1.380 (4) | C11A—H11A | 0.9300 |
C11—H11 | 0.9300 | C12A—C13A | 1.376 (3) |
C12—C13 | 1.359 (4) | C12A—H12A | 0.9300 |
C12—H12 | 0.9300 | C13A—C14A | 1.385 (3) |
C13—C14 | 1.378 (3) | C13A—H13A | 0.9300 |
C13—H13 | 0.9300 | C14A—O2A | 1.362 (2) |
C14—O2 | 1.356 (3) | C15A—O2A | 1.420 (2) |
C15—O2 | 1.416 (3) | C15A—C16A | 1.485 (3) |
C15—C16 | 1.489 (4) | C15A—H15C | 0.9700 |
C15—H15A | 0.9700 | C15A—H15D | 0.9700 |
C15—H15B | 0.9700 | C16A—H16D | 0.9600 |
C16—H16A | 0.9600 | C16A—H16E | 0.9600 |
C16—H16B | 0.9600 | C16A—H16F | 0.9600 |
C16—H16C | 0.9600 | C17A—C22A | 1.376 (2) |
C17—C22 | 1.376 (3) | C17A—C18A | 1.402 (2) |
C17—C18 | 1.402 (2) | C18A—O3A | 1.362 (2) |
C18—O3 | 1.359 (2) | C18A—C19A | 1.385 (2) |
C18—C19 | 1.385 (3) | C19A—C20A | 1.369 (3) |
C19—C20 | 1.374 (3) | C19A—H19A | 0.9300 |
C19—H19 | 0.9300 | C20A—C21A | 1.373 (3) |
C20—C21 | 1.370 (3) | C20A—H20A | 0.9300 |
C20—H20 | 0.9300 | C21A—C22A | 1.386 (3) |
C21—C22 | 1.386 (3) | C21A—H21A | 0.9300 |
C21—H21 | 0.9300 | C22A—H22A | 0.9300 |
C22—H22 | 0.9300 | C23A—O3A | 1.429 (2) |
C23—O3 | 1.429 (2) | C23A—C24A | 1.482 (3) |
C23—C24 | 1.484 (3) | C23A—H23C | 0.9700 |
C23—H23A | 0.9700 | C23A—H23D | 0.9700 |
C23—H23B | 0.9700 | C24A—H24D | 0.9600 |
C24—H24A | 0.9600 | C24A—H24E | 0.9600 |
C24—H24B | 0.9600 | C24A—H24F | 0.9600 |
C24—H24C | 0.9600 | N1—H1B | 0.8600 |
C1A—N1A | 1.460 (2) | N1A—H1A1 | 0.8600 |
N1—C1—C9 | 112.73 (15) | C2A—C1A—H1A | 108.0 |
N1—C1—C2 | 109.67 (14) | C8A—C2A—C3A | 108.26 (15) |
C9—C1—C2 | 109.74 (14) | C8A—C2A—C1A | 107.36 (13) |
N1—C1—H1 | 108.2 | C3A—C2A—C1A | 115.16 (15) |
C9—C1—H1 | 108.2 | C8A—C2A—H2A | 108.6 |
C2—C1—H1 | 108.2 | C3A—C2A—H2A | 108.6 |
C8—C2—C3 | 107.69 (16) | C1A—C2A—H2A | 108.6 |
C8—C2—C1 | 107.31 (15) | C4A—C3A—C2A | 114.66 (15) |
C3—C2—C1 | 115.21 (16) | C4A—C3A—H3A1 | 108.6 |
C8—C2—H2 | 108.8 | C2A—C3A—H3A1 | 108.6 |
C3—C2—H2 | 108.8 | C4A—C3A—H3A2 | 108.6 |
C1—C2—H2 | 108.8 | C2A—C3A—H3A2 | 108.6 |
C4—C3—C2 | 114.79 (16) | H3A1—C3A—H3A2 | 107.6 |
C4—C3—H3A | 108.6 | C3A—C4A—C5A | 113.24 (17) |
C2—C3—H3A | 108.6 | C3A—C4A—H4A1 | 108.9 |
C4—C3—H3B | 108.6 | C5A—C4A—H4A1 | 108.9 |
C2—C3—H3B | 108.6 | C3A—C4A—H4A2 | 108.9 |
H3A—C3—H3B | 107.5 | C5A—C4A—H4A2 | 108.9 |
C5—C4—C3 | 114.22 (18) | H4A1—C4A—H4A2 | 107.7 |
C5—C4—H4A | 108.7 | C4A—C5A—C6A | 113.95 (15) |
C3—C4—H4A | 108.7 | C4A—C5A—H5A1 | 108.8 |
C5—C4—H4B | 108.7 | C6A—C5A—H5A1 | 108.8 |
C3—C4—H4B | 108.7 | C4A—C5A—H5A2 | 108.8 |
H4A—C4—H4B | 107.6 | C6A—C5A—H5A2 | 108.8 |
C4—C5—C6 | 113.58 (16) | H5A1—C5A—H5A2 | 107.7 |
C4—C5—H5A | 108.8 | C8A—C6A—C5A | 107.13 (15) |
C6—C5—H5A | 108.8 | C8A—C6A—C7A | 106.65 (14) |
C4—C5—H5B | 108.8 | C5A—C6A—C7A | 116.51 (15) |
C6—C5—H5B | 108.8 | C8A—C6A—H6A | 108.8 |
H5A—C5—H5B | 107.7 | C5A—C6A—H6A | 108.8 |
C8—C6—C5 | 107.26 (16) | C7A—C6A—H6A | 108.8 |
C8—C6—C7 | 108.30 (15) | N1A—C7A—C17A | 110.19 (13) |
C5—C6—C7 | 115.01 (15) | N1A—C7A—C6A | 110.42 (13) |
C8—C6—H6 | 108.7 | C17A—C7A—C6A | 113.17 (13) |
C5—C6—H6 | 108.7 | N1A—C7A—H7A | 107.6 |
C7—C6—H6 | 108.7 | C17A—C7A—H7A | 107.6 |
N1—C7—C17 | 111.45 (14) | C6A—C7A—H7A | 107.6 |
N1—C7—C6 | 110.49 (14) | O1A—C8A—C2A | 123.74 (16) |
C17—C7—C6 | 110.87 (14) | O1A—C8A—C6A | 124.56 (16) |
N1—C7—H7 | 108.0 | C2A—C8A—C6A | 111.70 (15) |
C17—C7—H7 | 108.0 | C10A—C9A—C14A | 118.50 (16) |
C6—C7—H7 | 108.0 | C10A—C9A—C1A | 122.21 (15) |
O1—C8—C2 | 123.55 (19) | C14A—C9A—C1A | 119.28 (16) |
O1—C8—C6 | 124.69 (19) | C9A—C10A—C11A | 121.32 (19) |
C2—C8—C6 | 111.73 (15) | C9A—C10A—H10A | 119.3 |
C10—C9—C14 | 118.76 (19) | C11A—C10A—H10A | 119.3 |
C10—C9—C1 | 122.92 (18) | C12A—C11A—C10A | 119.4 (2) |
C14—C9—C1 | 118.23 (18) | C12A—C11A—H11A | 120.3 |
C9—C10—C11 | 121.2 (2) | C10A—C11A—H11A | 120.3 |
C9—C10—H10 | 119.4 | C11A—C12A—C13A | 120.68 (19) |
C11—C10—H10 | 119.4 | C11A—C12A—H12A | 119.7 |
C12—C11—C10 | 118.8 (3) | C13A—C12A—H12A | 119.7 |
C12—C11—H11 | 120.6 | C12A—C13A—C14A | 119.83 (19) |
C10—C11—H11 | 120.6 | C12A—C13A—H13A | 120.1 |
C13—C12—C11 | 121.3 (2) | C14A—C13A—H13A | 120.1 |
C13—C12—H12 | 119.3 | O2A—C14A—C13A | 124.40 (17) |
C11—C12—H12 | 119.3 | O2A—C14A—C9A | 115.37 (15) |
C12—C13—C14 | 119.9 (2) | C13A—C14A—C9A | 120.23 (19) |
C12—C13—H13 | 120.1 | O2A—C15A—C16A | 107.61 (18) |
C14—C13—H13 | 120.1 | O2A—C15A—H15C | 110.2 |
O2—C14—C13 | 124.5 (2) | C16A—C15A—H15C | 110.2 |
O2—C14—C9 | 115.44 (18) | O2A—C15A—H15D | 110.2 |
C13—C14—C9 | 120.1 (2) | C16A—C15A—H15D | 110.2 |
O2—C15—C16 | 107.1 (2) | H15C—C15A—H15D | 108.5 |
O2—C15—H15A | 110.3 | C15A—C16A—H16D | 109.5 |
C16—C15—H15A | 110.3 | C15A—C16A—H16E | 109.5 |
O2—C15—H15B | 110.3 | H16D—C16A—H16E | 109.5 |
C16—C15—H15B | 110.3 | C15A—C16A—H16F | 109.5 |
H15A—C15—H15B | 108.6 | H16D—C16A—H16F | 109.5 |
C15—C16—H16A | 109.5 | H16E—C16A—H16F | 109.5 |
C15—C16—H16B | 109.5 | C22A—C17A—C18A | 118.05 (15) |
H16A—C16—H16B | 109.5 | C22A—C17A—C7A | 122.34 (15) |
C15—C16—H16C | 109.5 | C18A—C17A—C7A | 119.57 (15) |
H16A—C16—H16C | 109.5 | O3A—C18A—C19A | 124.10 (16) |
H16B—C16—H16C | 109.5 | O3A—C18A—C17A | 115.66 (14) |
C22—C17—C18 | 118.06 (17) | C19A—C18A—C17A | 120.25 (17) |
C22—C17—C7 | 122.51 (16) | C20A—C19A—C18A | 119.99 (18) |
C18—C17—C7 | 119.43 (16) | C20A—C19A—H19A | 120.0 |
O3—C18—C19 | 124.35 (17) | C18A—C19A—H19A | 120.0 |
O3—C18—C17 | 115.60 (16) | C19A—C20A—C21A | 120.89 (18) |
C19—C18—C17 | 120.05 (18) | C19A—C20A—H20A | 119.6 |
C20—C19—C18 | 120.28 (19) | C21A—C20A—H20A | 119.6 |
C20—C19—H19 | 119.9 | C20A—C21A—C22A | 118.97 (19) |
C18—C19—H19 | 119.9 | C20A—C21A—H21A | 120.5 |
C21—C20—C19 | 120.57 (19) | C22A—C21A—H21A | 120.5 |
C21—C20—H20 | 119.7 | C17A—C22A—C21A | 121.78 (17) |
C19—C20—H20 | 119.7 | C17A—C22A—H22A | 119.1 |
C20—C21—C22 | 119.1 (2) | C21A—C22A—H22A | 119.1 |
C20—C21—H21 | 120.4 | O3A—C23A—C24A | 107.22 (18) |
C22—C21—H21 | 120.4 | O3A—C23A—H23C | 110.3 |
C17—C22—C21 | 121.93 (19) | C24A—C23A—H23C | 110.3 |
C17—C22—H22 | 119.0 | O3A—C23A—H23D | 110.3 |
C21—C22—H22 | 119.0 | C24A—C23A—H23D | 110.3 |
O3—C23—C24 | 107.78 (19) | H23C—C23A—H23D | 108.5 |
O3—C23—H23A | 110.2 | C23A—C24A—H24D | 109.5 |
C24—C23—H23A | 110.2 | C23A—C24A—H24E | 109.5 |
O3—C23—H23B | 110.2 | H24D—C24A—H24E | 109.5 |
C24—C23—H23B | 110.2 | C23A—C24A—H24F | 109.5 |
H23A—C23—H23B | 108.5 | H24D—C24A—H24F | 109.5 |
C23—C24—H24A | 109.5 | H24E—C24A—H24F | 109.5 |
C23—C24—H24B | 109.5 | C1—N1—C7 | 112.51 (14) |
H24A—C24—H24B | 109.5 | C1—N1—H1B | 123.7 |
C23—C24—H24C | 109.5 | C7—N1—H1B | 123.7 |
H24A—C24—H24C | 109.5 | C1A—N1A—C7A | 112.04 (13) |
H24B—C24—H24C | 109.5 | C1A—N1A—H1A1 | 124.0 |
N1A—C1A—C9A | 111.76 (14) | C7A—N1A—H1A1 | 124.0 |
N1A—C1A—C2A | 109.47 (13) | C14—O2—C15 | 120.69 (19) |
C9A—C1A—C2A | 111.38 (13) | C18—O3—C23 | 119.19 (15) |
N1A—C1A—H1A | 108.0 | C14A—O2A—C15A | 119.74 (16) |
C9A—C1A—H1A | 108.0 | C18A—O3A—C23A | 119.32 (15) |
N1—C1—C2—C8 | −59.41 (19) | C8A—C6A—C7A—N1A | 57.59 (17) |
C9—C1—C2—C8 | 176.24 (15) | C5A—C6A—C7A—N1A | −61.93 (18) |
N1—C1—C2—C3 | 60.5 (2) | C8A—C6A—C7A—C17A | −178.36 (14) |
C9—C1—C2—C3 | −63.9 (2) | C5A—C6A—C7A—C17A | 62.12 (19) |
C8—C2—C3—C4 | 50.3 (2) | C3A—C2A—C8A—O1A | 116.7 (2) |
C1—C2—C3—C4 | −69.4 (2) | C1A—C2A—C8A—O1A | −118.4 (2) |
C2—C3—C4—C5 | −41.6 (2) | C3A—C2A—C8A—C6A | −63.49 (19) |
C3—C4—C5—C6 | 43.3 (2) | C1A—C2A—C8A—C6A | 61.42 (19) |
C4—C5—C6—C8 | −53.8 (2) | C5A—C6A—C8A—O1A | −115.0 (2) |
C4—C5—C6—C7 | 66.7 (2) | C7A—C6A—C8A—O1A | 119.6 (2) |
C8—C6—C7—N1 | 55.34 (19) | C5A—C6A—C8A—C2A | 65.14 (19) |
C5—C6—C7—N1 | −64.60 (19) | C7A—C6A—C8A—C2A | −60.28 (18) |
C8—C6—C7—C17 | 179.42 (15) | N1A—C1A—C9A—C10A | −22.4 (2) |
C5—C6—C7—C17 | 59.5 (2) | C2A—C1A—C9A—C10A | 100.38 (19) |
C3—C2—C8—O1 | 114.5 (2) | N1A—C1A—C9A—C14A | 159.10 (15) |
C1—C2—C8—O1 | −120.9 (2) | C2A—C1A—C9A—C14A | −78.10 (19) |
C3—C2—C8—C6 | −63.8 (2) | C14A—C9A—C10A—C11A | 0.3 (3) |
C1—C2—C8—C6 | 60.8 (2) | C1A—C9A—C10A—C11A | −178.19 (18) |
C5—C6—C8—O1 | −112.5 (2) | C9A—C10A—C11A—C12A | 0.6 (3) |
C7—C6—C8—O1 | 122.8 (2) | C10A—C11A—C12A—C13A | −1.0 (3) |
C5—C6—C8—C2 | 65.9 (2) | C11A—C12A—C13A—C14A | 0.5 (3) |
C7—C6—C8—C2 | −58.8 (2) | C12A—C13A—C14A—O2A | −179.41 (18) |
N1—C1—C9—C10 | −23.5 (3) | C12A—C13A—C14A—C9A | 0.4 (3) |
C2—C1—C9—C10 | 99.1 (2) | C10A—C9A—C14A—O2A | 179.03 (16) |
N1—C1—C9—C14 | 160.12 (16) | C1A—C9A—C14A—O2A | −2.4 (2) |
C2—C1—C9—C14 | −77.3 (2) | C10A—C9A—C14A—C13A | −0.8 (3) |
C14—C9—C10—C11 | 0.5 (3) | C1A—C9A—C14A—C13A | 177.77 (16) |
C1—C9—C10—C11 | −175.9 (2) | N1A—C7A—C17A—C22A | 37.4 (2) |
C9—C10—C11—C12 | −0.3 (4) | C6A—C7A—C17A—C22A | −86.8 (2) |
C10—C11—C12—C13 | 0.4 (4) | N1A—C7A—C17A—C18A | −140.27 (15) |
C11—C12—C13—C14 | −0.7 (4) | C6A—C7A—C17A—C18A | 95.57 (18) |
C12—C13—C14—O2 | −179.9 (2) | C22A—C17A—C18A—O3A | 177.77 (15) |
C12—C13—C14—C9 | 1.0 (3) | C7A—C17A—C18A—O3A | −4.5 (2) |
C10—C9—C14—O2 | 180.0 (2) | C22A—C17A—C18A—C19A | −2.6 (2) |
C1—C9—C14—O2 | −3.5 (3) | C7A—C17A—C18A—C19A | 175.13 (15) |
C10—C9—C14—C13 | −0.8 (3) | O3A—C18A—C19A—C20A | −177.73 (17) |
C1—C9—C14—C13 | 175.74 (18) | C17A—C18A—C19A—C20A | 2.7 (3) |
N1—C7—C17—C22 | 24.0 (2) | C18A—C19A—C20A—C21A | −0.4 (3) |
C6—C7—C17—C22 | −99.5 (2) | C19A—C20A—C21A—C22A | −1.9 (3) |
N1—C7—C17—C18 | −156.54 (16) | C18A—C17A—C22A—C21A | 0.3 (3) |
C6—C7—C17—C18 | 79.9 (2) | C7A—C17A—C22A—C21A | −177.36 (18) |
C22—C17—C18—O3 | 179.19 (17) | C20A—C21A—C22A—C17A | 1.9 (3) |
C7—C17—C18—O3 | −0.3 (2) | C9—C1—N1—C7 | −177.56 (15) |
C22—C17—C18—C19 | −0.8 (3) | C2—C1—N1—C7 | 59.85 (19) |
C7—C17—C18—C19 | 179.73 (17) | C17—C7—N1—C1 | 178.51 (14) |
O3—C18—C19—C20 | −179.18 (18) | C6—C7—N1—C1 | −57.74 (19) |
C17—C18—C19—C20 | 0.8 (3) | C9A—C1A—N1A—C7A | −176.10 (13) |
C18—C19—C20—C21 | −0.1 (3) | C2A—C1A—N1A—C7A | 60.01 (17) |
C19—C20—C21—C22 | −0.6 (3) | C17A—C7A—N1A—C1A | 174.44 (13) |
C18—C17—C22—C21 | 0.1 (3) | C6A—C7A—N1A—C1A | −59.81 (17) |
C7—C17—C22—C21 | 179.55 (18) | C13—C14—O2—C15 | −9.5 (3) |
C20—C21—C22—C17 | 0.6 (3) | C9—C14—O2—C15 | 169.7 (2) |
N1A—C1A—C2A—C8A | −58.99 (18) | C16—C15—O2—C14 | −174.7 (2) |
C9A—C1A—C2A—C8A | 176.90 (14) | C19—C18—O3—C23 | 0.6 (3) |
N1A—C1A—C2A—C3A | 61.64 (18) | C17—C18—O3—C23 | −179.40 (17) |
C9A—C1A—C2A—C3A | −62.47 (18) | C24—C23—O3—C18 | 171.1 (2) |
C8A—C2A—C3A—C4A | 50.9 (2) | C13A—C14A—O2A—C15A | −6.7 (3) |
C1A—C2A—C3A—C4A | −69.3 (2) | C9A—C14A—O2A—C15A | 173.51 (16) |
C2A—C3A—C4A—C5A | −42.5 (2) | C16A—C15A—O2A—C14A | −176.14 (18) |
C3A—C4A—C5A—C6A | 44.4 (2) | C19A—C18A—O3A—C23A | −4.5 (3) |
C4A—C5A—C6A—C8A | −54.4 (2) | C17A—C18A—O3A—C23A | 175.13 (16) |
C4A—C5A—C6A—C7A | 64.9 (2) | C24A—C23A—O3A—C18A | 178.68 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
C23—H23A···O1A | 0.97 | 2.42 | 3.311 (3) | 153 |
C23A—H23C···O1 | 0.97 | 2.43 | 3.297 (3) | 149 |
Experimental details
Crystal data | |
Chemical formula | C24H29NO3 |
Mr | 379.49 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 9.7981 (3), 13.6139 (5), 16.7098 (6) |
α, β, γ (°) | 74.363 (2), 80.464 (2), 83.563 (2) |
V (Å3) | 2111.42 (13) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.35 × 0.28 × 0.22 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2004) |
Tmin, Tmax | 0.973, 0.983 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 27579, 9839, 6037 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.673 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.150, 1.02 |
No. of reflections | 9839 |
No. of parameters | 509 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.53, −0.45 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
C23—H23A···O1A | 0.97 | 2.42 | 3.311 (3) | 153 |
C23A—H23C···O1 | 0.97 | 2.43 | 3.297 (3) | 149 |
Acknowledgements
The authors acknowledge the Department of Chemistry, IIT Madras, for the X-ray data collection.
References
Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Jeyaraman, R. & Avila, S. (1981). Chem. Rev. 81, 149–174. CrossRef CAS Web of Science Google Scholar
Kalsi, P. S. (1997). In Stereochemistry: Conformation and Mechanism. New Delhi: New Age International (P) Ltd. Google Scholar
Park, D. H., Jeong, Y. T. & Parthiban, P. (2011). J. Mol. Struct. 1005, 31–44. Web of Science CrossRef CAS Google Scholar
Park, D. H., Ramkumar, V. & Parthiban, P. (2012b). Acta Cryst. E68, o2841. CSD CrossRef IUCr Journals Google Scholar
Park, D. H., Venkatesn, J., Kim, S. K. & Prthiban, P. (2012a). Bioorg. Med. Chem. Lett. 22, 6004–6009. Web of Science CSD CrossRef CAS PubMed Google Scholar
Parthiban, P., Ramkumar, V. & Jeong, Y. T. (2009b). Acta Cryst. E65, o3103. Web of Science CSD CrossRef IUCr Journals Google Scholar
Parthiban, P., Ramkumar, V., Kim, M. S., Son, S. M. & Jeong, Y. T. (2009a). Acta Cryst. E65, o1383. Web of Science CSD CrossRef IUCr Journals Google Scholar
Parthiban, P., Ramkumar, V., Park, D. H. & Jeong, Y. T. (2011b). Acta Cryst. E67, o1475–o1476. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Parthiban, P., Rathika, P., Park, K. S. & Jeong, Y. T. (2010b). Monatsh. Chem. 141, 79–93. Web of Science CrossRef CAS Google Scholar
Parthiban, P., Rathika, P., Ramkumar, V., Son, S. M. & Jeong, Y. T. (2010a). Bioorg. Med. Chem. Lett. 20, 1642–1647. Web of Science CSD CrossRef CAS PubMed Google Scholar
Parthiban, P., Subalakshmi, V., Balasubramanian, K., Islam, Md. N., Choi, J. S. & Jeong, Y. T. (2011a). Bioorg. Med. Chem. Lett. 21, 2287–2296. Web of Science CSD CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Nitrogen containing heterocycles are useful building-blocks of the construction of various pharmacologically important molecules. Since the 3-azabicyclononanes are displying diverse biological actions (Park et al., 2012a; Parthiban et al., 2010a, 2010b, 2011a; Jeyaraman & Avila, 1981), and the biological actions mainly depend on the stereochemistry of the molecules, the synthesis as well as stereochemical analysis of any biologically active molecules are of importance in the drug-design and drug-devlopement programs. Based on the above points, we synthesized the title compound, in order to examine the configurational and conformational status by single-crystal X-ray studies.
Careful examination of the asymmery parameters and torsion angles of the title compound reveal that the values are similar to its analogous compounds (Parthiban et al., 2009a, 2009b, 2011b; Park et al. 2012b). 2,4-Bis(4-ethoxyphenyl)-3-azabicyclo[3.3.1]nonan-9-one is the positional isomer of the title compound that exists in the twin-chair conformation. The impotant torsion angles of the title compound, viz., C2—C8—C6—C7 (-58.8 (2)°), C1—C2—C8—C6 (60.8 (2)°), C2—C8—C6—C5 (65.9 (2)°) and C3—C2—C8—C6 (-63.8 (2)°) insist that the bicycle exists in twin-chair conformation. However, the cyclohexanone torsion angles are more deviated than the piperidone ring as well as well the ideal chair cyclohexanone torsion angle of 56° (Kalsi, 1997). The comparision of above with the corresponding torsion angles of the para-isomer [-62.5 (2), 62.3 (2), 62.6 (2) and -62.6 (2)°, respectively] indicate that in the title compound, the cyclohexnone ring is more flattened than the cyclohexanone of its para-isomer. The above stereochemistry is further witnessed by the Cremer & Pople (1975) ring puckering parameters. For the piperidone ring of the title compound, the total puckering amplitude, QT is 0.5970 Å and the phase angle θ is 176.66°, for the cyclohexanone, QT = 0.5590 Å and θ = 163.39°. The same for the para-isomer are, QT = 0.5999 Å and θ = 173.84° (piperidone) and QT = 0.5643 Å and θ = 168.44°(cyclohexanone). Further, the orientation of the ethoxyphenyl groups on both sides of the secondary amino group are identified by their torsion angles. The torsion angle of C8—C2—C1—C9 and C8—C6—C7—C17 are 176.24 (15) and -179.42 (15)°, respectively.
The two benzene rings in two independent molecules are inclined to each other with angles of 41.3 (1) and 24.1 (1)°, respectively. In the crystal, weak intermolecular C—H···O interactions (Table 1) link independent molecules into dimer.