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The title compound, C18H19NO, in racemic form, was obtained by the reaction of naphthalene-1-carboxaldehyde with 1-aza­bicyclo­[2.2.2]octan-3-one in the presence of methano­lic potassium hydroxide and subsequent reduction of the product with sodium borohydride to the secondary alcohol. The double bond linking the 1-naphthyl and 1-aza­bicyclo­[2.2.2]octan-3-ol moieties has Z geometry. The C=C-CH=C torsion angle [42.4 (2)°] indicates a deviation of the 1-naphthyl ring from the plane of the double bond connected to the aza­bicyclic ring. Part of the 1-aza­bicyclo­[2.2.2]octan-3-ol moiety is disordered, with the approximate ratio of occupancies being 63:37.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807041682/lh2484sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807041682/lh2484Isup2.hkl
Contains datablock I

CCDC reference: 660371

Key indicators

  • Single-crystal X-ray study
  • T = 90 K
  • Mean [sigma](C-C) = 0.002 Å
  • Disorder in main residue
  • R factor = 0.047
  • wR factor = 0.126
  • Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C13 PLAT301_ALERT_3_C Main Residue Disorder ......................... 13.00 Perc. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C7 - C8 ... 1.33 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 1
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C9 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C9' = ... S PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Recently, we have reported (Sekhar et al., 2007) on the radio- sensitizing activity of N-arylsubstituted rac-(Z)-2- (1H-indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-ols. In addition to these indole analogues, we also synthesized 1-azabicyclo[2.2.2]octan-3-ols linked to non-indolic systems, such 1-naphthyl systems, to compare their radio-sensitizing activities with those of the indole analogs.

The crystal structure of the title compound confirmed the molecular structure and atom connectivity as illustrated in Fig. 1. The title compound comprises a 1-azabicyclo[2.2.2]octan-3-ol moiety and a 1-naphthyl group linked via the C7=C8 bond that has the Z geometry. The bond angles around the C7 and C8 atoms deviate from the ideal value [120°]; the angles for N1—C8—C9, C7=C8—N1, and C7=C8—C1 [113.35 (18), 124.84 (13), and 129.11 (14)°, respectively] are distorted. These deviations contribute to the release of the intramolecular nonbonded interactions. The C2=C1—C7=C8 torsion angle [-42.4 (2)°]indicates a deviation of the 1-naphthyl ring from the plane of the double bond connected to the azabicyclic ring. Also, the C1—C7 bond length, in comparison with the standard value for a Car—Csp2 single bond [1.470 (15) Å; Wilson, 1992], suggests absence of conjugation to the π electron system of the 1-naphthyl ring.

Related literature top

For related literature, see: Sekhar et al. (2007); Sonar et al. (2004); Wilson (1992).

Experimental top

The title compound was prepared according to the previously reported procedure of Sonar et al. (2004). Crystallization from ethyl acetate afforded colorless crystals. 1H NMR (CDCl3, p.p.m.): δ 1.45–2.13 (m, 3H), 1.94–2.04 (m, 2H), 2.12 (p, 1H), 2.79–3.05 (m, 4H), 4.47 (s, 1H), 6.99 (s, 1H), 7.44–7.53 (m, 3H), 7.75 (d, 1H), 7.84 (dd, 2H), 8.07 (dd, 1H). 13C NMR (CDCl3, p.p.m.): δ 19.22, 25.37, 31.21, 47.85, 48.88, 71.51, 120.17, 124.22, 125.53, 125.72, 125.83, 127.45, 128.67, 131.80, 132.16, 133.62, 153.52.

Refinement top

All H atoms were found in difference Fourier maps and subsequently placed in idealized positions with constrained distances of 0.99 Å (R2CH2), 1.00 Å (R3CH), 0.95 Å (CArH) and 0.84 Å (OH). Uiso(H) values were set to either 1.5Ueq (OH only) or 1.2Ueq of the attached atom. The crystal structure is centrosymmetric and therefore it is a racemic mixture of isomers. The two enantiomers have very nearly the same shape and the position of the hydroxyl group for each is very similar. This inevitably leads to a form of disorder in which one enantiomer substitutes for the other. In this case the occupancy factor ratio is 63:37. A single restraint equation was required in the least-squares refinement to ensure similarity of the C—O bond lengths of the two enantiomers (SADI in SHELXL97; Sheldrick, 1997).

Structure description top

Recently, we have reported (Sekhar et al., 2007) on the radio- sensitizing activity of N-arylsubstituted rac-(Z)-2- (1H-indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-ols. In addition to these indole analogues, we also synthesized 1-azabicyclo[2.2.2]octan-3-ols linked to non-indolic systems, such 1-naphthyl systems, to compare their radio-sensitizing activities with those of the indole analogs.

The crystal structure of the title compound confirmed the molecular structure and atom connectivity as illustrated in Fig. 1. The title compound comprises a 1-azabicyclo[2.2.2]octan-3-ol moiety and a 1-naphthyl group linked via the C7=C8 bond that has the Z geometry. The bond angles around the C7 and C8 atoms deviate from the ideal value [120°]; the angles for N1—C8—C9, C7=C8—N1, and C7=C8—C1 [113.35 (18), 124.84 (13), and 129.11 (14)°, respectively] are distorted. These deviations contribute to the release of the intramolecular nonbonded interactions. The C2=C1—C7=C8 torsion angle [-42.4 (2)°]indicates a deviation of the 1-naphthyl ring from the plane of the double bond connected to the azabicyclic ring. Also, the C1—C7 bond length, in comparison with the standard value for a Car—Csp2 single bond [1.470 (15) Å; Wilson, 1992], suggests absence of conjugation to the π electron system of the 1-naphthyl ring.

For related literature, see: Sekhar et al. (2007); Sonar et al. (2004); Wilson (1992).

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1995); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and local procedures.

Figures top
[Figure 1] Fig. 1. A view of the title molecule, with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. The azabicyclic ring is disordered and only the ring with the major occupancy is shown.
rac-(Z)-2-(1-Naphthylmethylene)-1-azabicyclo[2.2.2]octan-3-ol top
Crystal data top
C18H19NOF(000) = 568
Mr = 265.34Dx = 1.283 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3326 reflections
a = 6.1892 (1) Åθ = 1.0–27.5°
b = 8.8706 (2) ŵ = 0.08 mm1
c = 25.1693 (5) ÅT = 90 K
β = 96.0631 (8)°Block, colourless
V = 1374.11 (5) Å30.25 × 0.20 × 0.15 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
3132 independent reflections
Radiation source: fine-focus sealed tube2155 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
Detector resolution: 18 pixels mm-1θmax = 27.5°, θmin = 1.6°
ω scans at fixed χ = 55°h = 88
Absorption correction: multi-scan
SCALEPACK (Otwinowski & Minor, 1997)
k = 1111
Tmin = 0.981, Tmax = 0.988l = 3232
5940 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0611P)2 + 0.3438P]
where P = (Fo2 + 2Fc2)/3
3132 reflections(Δ/σ)max = 0.005
205 parametersΔρmax = 0.27 e Å3
1 restraintΔρmin = 0.25 e Å3
Crystal data top
C18H19NOV = 1374.11 (5) Å3
Mr = 265.34Z = 4
Monoclinic, P21/cMo Kα radiation
a = 6.1892 (1) ŵ = 0.08 mm1
b = 8.8706 (2) ÅT = 90 K
c = 25.1693 (5) Å0.25 × 0.20 × 0.15 mm
β = 96.0631 (8)°
Data collection top
Nonius KappaCCD
diffractometer
3132 independent reflections
Absorption correction: multi-scan
SCALEPACK (Otwinowski & Minor, 1997)
2155 reflections with I > 2σ(I)
Tmin = 0.981, Tmax = 0.988Rint = 0.035
5940 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0471 restraint
wR(F2) = 0.126H-atom parameters constrained
S = 1.02Δρmax = 0.27 e Å3
3132 reflectionsΔρmin = 0.25 e Å3
205 parameters
Special details top

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.

Some disorder caused by this being a mixture of isomers. The model is a compromise but the fit is quite good.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N10.79527 (18)0.14764 (14)0.08644 (5)0.0224 (3)
C10.7826 (2)0.17785 (16)0.12963 (6)0.0191 (3)
C20.9384 (2)0.19584 (17)0.09501 (6)0.0222 (3)
H20.93020.13710.06330.027*
C31.1100 (2)0.29966 (18)0.10563 (6)0.0250 (4)
H31.21520.31050.08100.030*
C41.1258 (2)0.38435 (18)0.15093 (6)0.0255 (4)
H41.24450.45180.15810.031*
C50.9682 (2)0.37340 (17)0.18746 (6)0.0219 (3)
C60.7926 (2)0.26997 (16)0.17679 (6)0.0189 (3)
C70.6004 (2)0.07164 (18)0.11800 (6)0.0235 (3)
H70.46240.10770.12550.028*
C80.6021 (2)0.06755 (19)0.09843 (6)0.0266 (4)
C90.3949 (6)0.1687 (4)0.09465 (13)0.0179 (7)0.630 (3)
H90.35070.18900.13110.021*0.630 (3)
O10.2307 (2)0.0842 (2)0.06349 (7)0.0257 (5)0.630 (3)
H1O0.11030.09850.07520.038*0.630 (3)
C9'0.3883 (12)0.1425 (9)0.0770 (2)0.0179 (7)0.370 (3)
H9'0.32600.09490.04270.021*0.370 (3)
O1'0.2545 (4)0.1171 (4)0.11801 (11)0.0263 (9)0.370 (3)
H1O'0.12380.11530.10500.039*0.370 (3)
C100.4502 (2)0.31263 (17)0.06831 (6)0.0217 (3)
H100.32140.38100.06250.026*
C110.601 (2)0.3579 (11)0.1187 (5)0.032 (2)0.370 (3)
H11A0.62080.46870.11920.038*0.370 (3)
H11B0.53250.32900.15100.038*0.370 (3)
C11'0.6166 (12)0.3993 (6)0.1062 (3)0.0263 (11)0.630 (3)
H11C0.55260.42950.13900.032*0.630 (3)
H11D0.66620.49090.08860.032*0.630 (3)
C120.8142 (2)0.28499 (19)0.12014 (6)0.0286 (4)
H12A0.86720.25760.15740.034*
H12B0.92000.35540.10670.034*
C130.5584 (3)0.2930 (2)0.01790 (7)0.0416 (5)
H13A0.59850.39270.00430.050*
H13B0.45650.24400.00980.050*
C140.7627 (2)0.19550 (19)0.02959 (6)0.0264 (4)
H14A0.74980.10510.00640.032*
H14B0.89110.25340.02090.032*
C150.9787 (3)0.46434 (19)0.23397 (6)0.0285 (4)
H151.09770.53140.24160.034*
C160.8215 (3)0.4573 (2)0.26784 (6)0.0321 (4)
H160.83000.52010.29860.039*
C170.6457 (3)0.35661 (19)0.25718 (6)0.0283 (4)
H170.53520.35270.28060.034*
C180.6331 (2)0.26472 (18)0.21344 (6)0.0228 (3)
H180.51550.19590.20740.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0157 (6)0.0194 (7)0.0326 (7)0.0002 (5)0.0044 (5)0.0048 (6)
C10.0175 (7)0.0144 (7)0.0248 (7)0.0022 (6)0.0011 (6)0.0019 (6)
C20.0232 (7)0.0188 (8)0.0244 (7)0.0046 (6)0.0021 (6)0.0006 (6)
C30.0206 (7)0.0221 (8)0.0332 (8)0.0027 (6)0.0070 (6)0.0052 (7)
C40.0188 (7)0.0193 (8)0.0378 (9)0.0022 (6)0.0001 (6)0.0036 (7)
C50.0203 (7)0.0171 (8)0.0270 (8)0.0016 (6)0.0045 (6)0.0015 (6)
C60.0193 (7)0.0151 (7)0.0214 (7)0.0028 (6)0.0016 (5)0.0011 (6)
C70.0156 (7)0.0249 (8)0.0300 (8)0.0014 (6)0.0023 (6)0.0055 (7)
C80.0147 (7)0.0260 (9)0.0394 (9)0.0007 (6)0.0039 (6)0.0096 (7)
C90.0169 (8)0.0195 (17)0.017 (2)0.0000 (10)0.0003 (15)0.0030 (15)
O10.0133 (8)0.0252 (10)0.0382 (11)0.0003 (7)0.0011 (7)0.0080 (8)
C9'0.0169 (8)0.0195 (17)0.017 (2)0.0000 (10)0.0003 (15)0.0030 (15)
O1'0.0130 (14)0.040 (2)0.0262 (17)0.0033 (13)0.0056 (11)0.0075 (13)
C100.0165 (7)0.0187 (8)0.0298 (8)0.0048 (6)0.0027 (6)0.0012 (6)
C110.035 (4)0.017 (5)0.042 (6)0.001 (4)0.002 (3)0.006 (3)
C11'0.0203 (17)0.017 (3)0.042 (3)0.007 (2)0.0035 (18)0.0090 (19)
C120.0215 (8)0.0330 (10)0.0305 (8)0.0004 (7)0.0010 (6)0.0049 (7)
C130.0270 (9)0.0675 (14)0.0314 (9)0.0121 (9)0.0084 (7)0.0178 (9)
C140.0253 (8)0.0268 (9)0.0287 (8)0.0017 (7)0.0098 (6)0.0004 (7)
C150.0269 (8)0.0241 (9)0.0324 (9)0.0015 (7)0.0069 (7)0.0044 (7)
C160.0388 (9)0.0305 (10)0.0252 (8)0.0046 (8)0.0051 (7)0.0067 (7)
C170.0299 (8)0.0324 (10)0.0225 (8)0.0059 (7)0.0029 (6)0.0011 (7)
C180.0220 (7)0.0217 (8)0.0243 (8)0.0005 (6)0.0005 (6)0.0028 (6)
Geometric parameters (Å, º) top
N1—C81.4495 (19)O1'—H1O'0.8400
N1—C121.482 (2)C10—C131.506 (2)
N1—C141.4858 (19)C10—C11'1.534 (8)
C1—C21.376 (2)C10—C111.548 (15)
C1—C61.437 (2)C10—H101.0000
C1—C71.475 (2)C11—C121.464 (14)
C2—C31.410 (2)C11—H11A0.9900
C2—H20.9500C11—H11B0.9900
C3—C41.360 (2)C11'—C121.599 (7)
C3—H30.9500C11'—H11C0.9900
C4—C51.413 (2)C11'—H11D0.9900
C4—H40.9500C12—H12A0.9900
C5—C151.418 (2)C12—H12B0.9900
C5—C61.426 (2)C13—C141.535 (2)
C6—C181.421 (2)C13—H13A0.9900
C7—C81.330 (2)C13—H13B0.9900
C7—H70.9500C14—H14A0.9900
C8—C9'1.528 (8)C14—H14B0.9900
C8—C91.560 (4)C15—C161.361 (2)
C9—O11.429 (3)C15—H150.9500
C9—C101.495 (4)C16—C171.412 (2)
C9—H91.0000C16—H160.9500
O1—H1O0.8400C17—C181.365 (2)
C9'—O1'1.408 (6)C17—H170.9500
C9'—C101.578 (8)C18—H180.9500
C9'—H9'1.0000
C8—N1—C12107.51 (12)C9—C10—H10111.5
C8—N1—C14108.03 (12)C13—C10—H10111.5
C12—N1—C14108.10 (12)C11'—C10—H10105.0
C2—C1—C6119.03 (13)C11—C10—H10111.5
C2—C1—C7121.38 (13)C9'—C10—H10113.5
C6—C1—C7119.51 (13)C12—C11—C10111.7 (8)
C1—C2—C3121.35 (14)C12—C11—H11A109.3
C1—C2—H2119.3C10—C11—H11A109.3
C3—C2—H2119.3C12—C11—H11B109.3
C4—C3—C2120.37 (14)C10—C11—H11B109.3
C4—C3—H3119.8H11A—C11—H11B107.9
C2—C3—H3119.8C10—C11'—C12105.4 (4)
C3—C4—C5120.93 (14)C10—C11'—H11C110.7
C3—C4—H4119.5C12—C11'—H11C110.7
C5—C4—H4119.5C10—C11'—H11D110.7
C4—C5—C15121.57 (14)C12—C11'—H11D110.7
C4—C5—C6119.13 (13)H11C—C11'—H11D108.8
C15—C5—C6119.30 (14)C11—C12—N1109.4 (5)
C18—C6—C5117.81 (13)N1—C12—C11'112.5 (3)
C18—C6—C1123.05 (13)C11—C12—H12A109.8
C5—C6—C1119.13 (13)N1—C12—H12A109.8
C8—C7—C1129.11 (14)C11'—C12—H12A122.2
C8—C7—H7115.4C11—C12—H12B109.8
C1—C7—H7115.4N1—C12—H12B109.8
C7—C8—N1124.84 (13)C11'—C12—H12B92.5
C7—C8—C9'119.6 (3)H12A—C12—H12B108.2
N1—C8—C9'114.6 (3)C10—C13—C14109.53 (13)
C7—C8—C9121.19 (18)C10—C13—H13A109.8
N1—C8—C9113.35 (18)C14—C13—H13A109.8
O1—C9—C10112.8 (3)C10—C13—H13B109.8
O1—C9—C8105.3 (2)C14—C13—H13B109.8
C10—C9—C8107.0 (2)H13A—C13—H13B108.2
O1—C9—H9110.5N1—C14—C13111.77 (12)
C10—C9—H9110.5N1—C14—H14A109.3
C8—C9—H9110.5C13—C14—H14A109.3
O1'—C9'—C8103.1 (5)N1—C14—H14B109.3
O1'—C9'—C10115.1 (4)C13—C14—H14B109.3
C8—C9'—C10104.5 (4)H14A—C14—H14B107.9
O1'—C9'—H9'111.2C16—C15—C5121.16 (14)
C8—C9'—H9'111.2C16—C15—H15119.4
C10—C9'—H9'111.2C5—C15—H15119.4
C9'—O1'—H1O'109.5C15—C16—C17119.84 (14)
C9—C10—C13114.70 (18)C15—C16—H16120.1
C9—C10—C11'108.8 (2)C17—C16—H16120.1
C13—C10—C11'104.7 (3)C18—C17—C16120.54 (15)
C9—C10—C1190.3 (3)C18—C17—H17119.7
C13—C10—C11115.9 (5)C16—C17—H17119.7
C13—C10—C9'98.2 (2)C17—C18—C6121.31 (14)
C11'—C10—C9'123.4 (3)C17—C18—H18119.3
C11—C10—C9'105.6 (4)C6—C18—H18119.3
C6—C1—C2—C31.7 (2)C8—C9—C10—C1170.2 (5)
C7—C1—C2—C3178.68 (13)O1—C9—C10—C9'38.9 (11)
C1—C2—C3—C40.4 (2)C8—C9—C10—C9'76.5 (12)
C2—C3—C4—C51.8 (2)O1'—C9'—C10—C933.5 (8)
C3—C4—C5—C15177.98 (14)C8—C9'—C10—C978.8 (12)
C3—C4—C5—C61.0 (2)O1'—C9'—C10—C13171.8 (4)
C4—C5—C6—C18178.17 (13)C8—C9'—C10—C1375.9 (3)
C15—C5—C6—C180.9 (2)O1'—C9'—C10—C11'74.6 (6)
C4—C5—C6—C11.0 (2)C8—C9'—C10—C11'37.7 (5)
C15—C5—C6—C1179.93 (13)O1'—C9'—C10—C1168.3 (7)
C2—C1—C6—C18176.80 (13)C8—C9'—C10—C1144.0 (6)
C7—C1—C6—C180.2 (2)C9—C10—C11—C1281.2 (5)
C2—C1—C6—C52.4 (2)C13—C10—C11—C1236.6 (6)
C7—C1—C6—C5179.41 (13)C11'—C10—C11—C1293 (2)
C2—C1—C7—C842.4 (2)C9'—C10—C11—C1270.8 (6)
C6—C1—C7—C8140.60 (17)C9—C10—C11'—C1255.3 (4)
C1—C7—C8—N13.0 (3)C13—C10—C11'—C1267.7 (3)
C1—C7—C8—C9'165.1 (2)C11—C10—C11'—C1262 (2)
C1—C7—C8—C9173.36 (17)C9'—C10—C11'—C1242.7 (5)
C12—N1—C8—C7119.28 (17)C10—C11—C12—N122.5 (6)
C14—N1—C8—C7124.27 (17)C10—C11—C12—C11'81 (3)
C12—N1—C8—C9'72.0 (3)C8—N1—C12—C1144.8 (4)
C14—N1—C8—C9'44.4 (3)C14—N1—C12—C1171.6 (4)
C12—N1—C8—C951.73 (19)C8—N1—C12—C11'63.9 (3)
C14—N1—C8—C964.72 (19)C14—N1—C12—C11'52.5 (3)
C7—C8—C9—O156.6 (3)C10—C11'—C12—C1174 (2)
N1—C8—C9—O1132.0 (2)C10—C11'—C12—N19.9 (4)
C9'—C8—C9—O134.1 (10)C9—C10—C13—C1455.7 (2)
C7—C8—C9—C10176.91 (17)C11'—C10—C13—C1463.5 (3)
N1—C8—C9—C1011.7 (2)C11—C10—C13—C1447.6 (4)
C9'—C8—C9—C1086.2 (12)C9'—C10—C13—C1464.2 (3)
C7—C8—C9'—O1'48.6 (5)C8—N1—C14—C1357.09 (18)
N1—C8—C9'—O1'142.1 (3)C12—N1—C14—C1358.97 (17)
C9—C8—C9'—O1'51.6 (9)C10—C13—C14—N10.4 (2)
C7—C8—C9'—C10169.3 (2)C4—C5—C15—C16177.35 (15)
N1—C8—C9'—C1021.4 (3)C6—C5—C15—C161.7 (2)
C9—C8—C9'—C1069.1 (11)C5—C15—C16—C170.9 (2)
O1—C9—C10—C1366.7 (3)C15—C16—C17—C180.8 (2)
C8—C9—C10—C1348.7 (2)C16—C17—C18—C61.6 (2)
O1—C9—C10—C11'176.5 (3)C5—C6—C18—C170.7 (2)
C8—C9—C10—C11'68.1 (3)C1—C6—C18—C17178.45 (14)
O1—C9—C10—C11174.5 (5)

Experimental details

Crystal data
Chemical formulaC18H19NO
Mr265.34
Crystal system, space groupMonoclinic, P21/c
Temperature (K)90
a, b, c (Å)6.1892 (1), 8.8706 (2), 25.1693 (5)
β (°) 96.0631 (8)
V3)1374.11 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.25 × 0.20 × 0.15
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
SCALEPACK (Otwinowski & Minor, 1997)
Tmin, Tmax0.981, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections
5940, 3132, 2155
Rint0.035
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.126, 1.02
No. of reflections3132
No. of parameters205
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.27, 0.25

Computer programs: COLLECT (Nonius, 1999), SCALEPACK (Otwinowski & Minor, 1997), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997), XP in SHELXTL/PC (Sheldrick, 1995), SHELXL97 (Sheldrick, 1997) and local procedures.

 

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