(Z)-4-[3-(3-Oxoquinuclidin-2-ylidene­meth­yl)-1H-indol-1-ylmeth­yl]benzo­nitrile

Reddy, T.R.Y.; Penthala, N.R.; Parkin, S.; Crooks, P.A.

doi:10.1107/S1600536808030006

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2049

doi:10.1107/S1600536808030006

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(Z)-4-[3-(3-Oxoquinuclidin-2-ylidenemethyl)-1H-indol-1-ylmethyl]benzonitrile

Thirupathi Reddy Yerram Reddy,^a Narsimha Reddy Penthala,^a Sean Parkin ^b and Peter A. Crooks ^a ^*

^aDepartment of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, KY 40536, USA, and ^bDepartment of Chemistry, University of Kentucky, Lexington, KY 40506, USA
^*Correspondence e-mail: pcrooks@uky.edu

(Received 28 August 2008; accepted 17 September 2008; online 4 October 2008)

The title compound, C₂₄H₂₁N₃O, was prepared by the reaction of (Z)-2-(1H-indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-one with α-bromo-p-toluonitrile, under phase-transfer catalytic (PTC) conditions using triethylbenzylammonium chloride and 50% w/v aqueous NaOH solution in dichloromethane. The crystal structure indicates the presence of a double bond with Z geometry connecting the azabicyclic and indole groups.

Related literature

For related structures, see: Mason et al. (2003 ); Zarza et al. (1988 ). For related bond angles, see: Wilson (1992 ). For related literature, see: Sekhar et al. (2003 ); Sonar et al. (2007 ).

Experimental

Crystal data

C₂₄H₂₁N₃O
M_r = 367.44
Triclinic, $[P \overline 1]$
a = 9.0627 (2) Å
b = 10.7959 (3) Å
c = 11.6969 (4) Å
α = 99.1571 (13)°
β = 106.0935 (14)°
γ = 113.7908 (14)°
V = 957.16 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 90.0 (2) K
0.44 × 0.40 × 0.25 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ) T_min = 0.966, T_max = 0.980
20970 measured reflections
4385 independent reflections
2935 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.128
S = 1.04
4385 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: COLLECT (Nonius, 1998 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELX97 and local procedures.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808030006/om2261sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808030006/om2261Isup2.hkl

checkCIF report

Comment top

The molecular structure and the atom-numbering scheme are illustrated in Fig. 1. The indole ring is planar with bond distances and angles comparable with those previously reported for other indole derivatives (Mason et al., 2003; Zarza et al., 1988). The compound is the Z isomer, with the C11—C17 bond in a trans position with respect to the C3—C10 bond. The olefinic bond (C10=C11) has a nearly planar atomic arrangement, since the r.m.s. deviation from the best plane passing through atoms N2, C11,C17, C10 and C3 is 0.0188 (9) Å. Deviations from ideal geometry are observed in the bond angles around atoms C3, C10 and C11. The C10=C11—C17 bond angle is close to the standard planar triangular value of 120°, whereas the C2=C3—C10, C3—C10=C11 and C10=C11—C17 bond angles are more distorted due to the strain induced by the C10=C11—C18=O1 conjugated double bond linkage. These bond angle deformations, which require little energy, are needed to relieve the strain of intramolecular interactions between non-bonded atoms. The azabicyclic system presents very small distortions around atoms N2, C13, C14, C15, C16 and C17. The value of the C2—C3—C10—C11 torsion angle [-5.1 (3)°] indicates the deviation of the indole ring from the plane of the double bond connected to the azabicyclic ring. The C3—C10 bond length, when compared with the standard value for a single bond connecting a C_ar atom to a Csp² atom (1.470 (15) Å; Wilson, 1992), suggests extensive conjugation, beginning at atom O1 and extending through to the indole ring. The bond angles in the azabicyclic system at C13, C14 and C15 are, on average, smaller than the standard tetrahedral value of 109.5°, while the bond angles at C12 and C16 are, on average, slightly larger than the ideal tetrahedral bond angle.

There are no significant intermolecular hydrogen-bonding interactions in the packing of this compound. The packing is essentially stabilized via van der Waals forces.

Related literature top

For related literature, see: Mason et al. (2003); Sekhar et al. (2003); Sonar et al. (2007); Wilson (1992); Zarza et al. (1988).

Experimental top

To a stirred solution of diisopropylamine (1.923 g, 19 mmol) in THF (20 ml) at 273 K under nitrogen was added a solution of 2.0 M n-butyllithium (9 ml, 18.8 mmol) and the mixture stirred at 273 K for 30 min. To this solution at 273 K, was added 1-aza-bicyclo[2.2.2]octan-3-one hydrochloride (1.5 g, 9.28 mmol) in one portion and stirring continued until the mixture completely dissolved (20 min). The temperature was lowered to 195 K and a solution of 1-acetyl-1H-indole-3-carboxaldehyde (1.722 g, 9.2 mmol) in THF (25 ml) was added dropwise. Stirring was continued for 30 min at this temperature and then for 90 min at 0°C. The reaction mixture was poured into saturated NaHCO₃ at 273 K and the resulting solution was extracted with CHCl₃ (3 x 15 ml). The combined organic extracts were dried over anhydrous Na₂SO₄ and evaporated to afford (Z)-2-(1-acetyl- 1H-indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-one, which was subsequently refluxed with sodium hydroxide solution (25 ml, 1 N) for 30 min. The reaction mixture was cooled to room temperature, and the yellow solid that separated was collected by filtration, washed with cold water and dried to afford the (Z)-2-(1H-indol-3-ylmethylene) -1-azabicyclo[2.2.2]octan-3-one.

To a stirred mixture of (Z)-2-(1H-indol-3-ylmethylene) -1-azabicyclo[2.2.2]octan-3-one (1.0 g, 3.96 mmol), 50% w/v aqueous NaOH solution (1.52 g, 19 mmol) and benzyltriethylammonium chloride (0.172 g, 0.75 mmol) in dichloromethane (DCM, 25 ml) at room temperature was added α-bromo-p-tolunitrile (0.78 g, 4.0 mmol) in one portion, then the reaction mixture was stirred vigorously for 1 hr until no (Z)-2-(1H-indol-3-ylmethylene)-1-azabicyclo[2.2.2] octan-3-one was detected by TLC. The organic layer was separated, washed exhaustively with water, dried with Na₂SO₄ and evaporated to afford the crude product. Crystallization from methanol gave a yellow crystalline product of compound (I) that was suitable for X-ray analysis. ¹H NMR (CDCl₃): δ 1.98–2.04 (m, 4H), 2.60 (p, 1H), 2.92–2.99 (m, 2H), 3.08–3.18 (m, 2H), 5.43 (s, 2H), 7.10–7.23 (m, 5H), 7.45 (s, 1H), 7.57 (d, J = 7.2 Hz, 2H), 7.87 (d, J = 7.2 Hz, 1H), 8.37 (s, 1H); ¹³C NMR (CDCl₃): δ 27.1, 41.1, 48.2, 50.8, 110.4, 111.5, 112.3, 118.0, 118.9, 119.9, 121.8, 123.5, 127.6, 129.3, 133.2, 134.2, 136.3, 141.7, 142.5, 205.7.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELX97 (Sheldrick, 2008) and local procedures.

Figures top

	Fig. 1. A view of the title molecule with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The formation of the title compound.

(Z)-4-[3-(3-Oxoquinuclidin-2-ylidenemethyl)-1H-indol-1- ylmethyl]benzonitrile top

Crystal data top

C₂₄H₂₁N₃O	Z = 2
M_r = 367.44	F(000) = 388
Triclinic, P1	D_x = 1.275 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0627 (2) Å	Cell parameters from 4341 reflections
b = 10.7959 (3) Å	θ = 1.0–27.5°
c = 11.6969 (4) Å	µ = 0.08 mm⁻¹
α = 99.1571 (13)°	T = 90 K
β = 106.0935 (14)°	Irregular block, colourless
γ = 113.7908 (14)°	0.44 × 0.40 × 0.25 mm
V = 957.16 (5) Å³

Data collection top

Nonius KappaCCD diffractometer	4385 independent reflections
Radiation source: fine-focus sealed tube	2935 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
Detector resolution: 18 pixels mm^-1	θ_max = 27.5°, θ_min = 1.9°
ω scans at fixed χ = 55°	h = −11→11
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −14→13
T_min = 0.966, T_max = 0.980	l = 0→15
20970 measured reflections

Refinement top

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0661P)² + 0.0538P] where P = (F_o² + 2F_c²)/3
4385 reflections	(Δ/σ)_max = 0.004
253 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₄H₂₁N₃O	γ = 113.7908 (14)°
M_r = 367.44	V = 957.16 (5) Å³
Triclinic, P1	Z = 2
a = 9.0627 (2) Å	Mo Kα radiation
b = 10.7959 (3) Å	µ = 0.08 mm⁻¹
c = 11.6969 (4) Å	T = 90 K
α = 99.1571 (13)°	0.44 × 0.40 × 0.25 mm
β = 106.0935 (14)°

Data collection top

Nonius KappaCCD diffractometer	4385 independent reflections
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	2935 reflections with I > 2σ(I)
T_min = 0.966, T_max = 0.980	R_int = 0.054
20970 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.128	H-atom parameters constrained
S = 1.04	Δρ_max = 0.22 e Å⁻³
4385 reflections	Δρ_min = −0.21 e Å⁻³
253 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 > 2σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.63840 (16)	0.43150 (13)	0.54539 (11)	0.0220 (3)
N2	0.29373 (16)	0.01430 (13)	0.25488 (12)	0.0241 (3)
N3	1.56395 (18)	0.85155 (14)	1.00029 (13)	0.0306 (3)
O1	0.00836 (14)	−0.22274 (12)	0.37598 (11)	0.0320 (3)
C2	0.53780 (19)	0.29481 (16)	0.46742 (15)	0.0243 (4)
H2	0.5404	0.2614	0.3882	0.029*
C3	0.43160 (19)	0.21170 (16)	0.51985 (14)	0.0228 (3)
C4	0.47183 (19)	0.30524 (16)	0.63990 (14)	0.0215 (3)
C5	0.4079 (2)	0.28731 (16)	0.73508 (15)	0.0251 (4)
H5	0.3221	0.1967	0.7294	0.030*
C6	0.4719 (2)	0.40387 (17)	0.83761 (15)	0.0287 (4)
H6	0.4307	0.3925	0.9036	0.034*
C7	0.5965 (2)	0.53862 (17)	0.84652 (16)	0.0296 (4)
H7	0.6366	0.6171	0.9177	0.036*
C8	0.6620 (2)	0.55952 (16)	0.75394 (15)	0.0258 (4)
H8	0.7465	0.6508	0.7598	0.031*
C9	0.59912 (19)	0.44119 (16)	0.65166 (14)	0.0221 (3)
C10	0.29595 (19)	0.06574 (15)	0.46778 (15)	0.0237 (4)
H10	0.2459	0.0273	0.5236	0.028*
C11	0.23045 (19)	−0.02341 (15)	0.35161 (14)	0.0225 (3)
C12	0.1480 (2)	0.00383 (16)	0.15034 (15)	0.0266 (4)
H12A	0.1881	0.0271	0.0822	0.032*
H12B	0.1124	0.0744	0.1797	0.032*
C13	−0.0109 (2)	−0.14677 (17)	0.09871 (16)	0.0301 (4)
H13A	−0.1140	−0.1411	0.1069	0.036*
H13B	−0.0382	−0.1885	0.0090	0.036*
C14	0.03321 (19)	−0.24051 (16)	0.17351 (15)	0.0259 (4)
H14	−0.0676	−0.3383	0.1441	0.031*
C15	0.1944 (2)	−0.24547 (17)	0.15857 (16)	0.0303 (4)
H15A	0.1687	−0.2881	0.0694	0.036*
H15B	0.2270	−0.3043	0.2066	0.036*
C16	0.3455 (2)	−0.09142 (16)	0.20803 (15)	0.0280 (4)
H16A	0.4442	−0.0848	0.2765	0.034*
H16B	0.3857	−0.0684	0.1399	0.034*
C17	0.0820 (2)	−0.16865 (16)	0.30955 (15)	0.0249 (4)
C18	0.76263 (19)	0.55154 (16)	0.52187 (14)	0.0235 (3)
H18A	0.7227	0.6243	0.5193	0.028*
H18B	0.7662	0.5186	0.4392	0.028*
C19	0.94360 (19)	0.61802 (15)	0.62085 (14)	0.0222 (3)
C20	1.04167 (19)	0.76546 (16)	0.67051 (15)	0.0264 (4)
H20	0.9969	0.8237	0.6379	0.032*
C21	1.2034 (2)	0.82836 (17)	0.76673 (15)	0.0284 (4)
H21	1.2684	0.9290	0.8012	0.034*
C22	1.26979 (19)	0.74218 (16)	0.81242 (14)	0.0238 (4)
C23	1.1756 (2)	0.59485 (16)	0.76076 (15)	0.0257 (4)
H23	1.2224	0.5365	0.7905	0.031*
C24	1.0130 (2)	0.53398 (16)	0.66567 (15)	0.0256 (4)
H24	0.9482	0.4334	0.6307	0.031*
C25	1.4347 (2)	0.80457 (16)	0.91607 (15)	0.0251 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0188 (6)	0.0228 (7)	0.0201 (7)	0.0072 (6)	0.0063 (5)	0.0052 (6)
N2	0.0228 (7)	0.0244 (7)	0.0227 (7)	0.0105 (6)	0.0066 (6)	0.0063 (6)
N3	0.0275 (8)	0.0302 (8)	0.0286 (8)	0.0114 (6)	0.0075 (7)	0.0067 (6)
O1	0.0327 (7)	0.0271 (6)	0.0347 (7)	0.0098 (5)	0.0162 (6)	0.0113 (5)
C2	0.0227 (8)	0.0239 (8)	0.0208 (8)	0.0099 (7)	0.0046 (7)	0.0026 (7)
C3	0.0214 (8)	0.0241 (8)	0.0208 (8)	0.0111 (7)	0.0055 (7)	0.0052 (7)
C4	0.0190 (8)	0.0230 (8)	0.0211 (8)	0.0108 (7)	0.0043 (6)	0.0068 (7)
C5	0.0222 (8)	0.0252 (9)	0.0251 (9)	0.0091 (7)	0.0081 (7)	0.0079 (7)
C6	0.0281 (9)	0.0324 (9)	0.0242 (9)	0.0123 (8)	0.0119 (7)	0.0069 (7)
C7	0.0298 (9)	0.0288 (9)	0.0255 (9)	0.0116 (8)	0.0106 (8)	0.0022 (7)
C8	0.0231 (8)	0.0230 (8)	0.0249 (9)	0.0081 (7)	0.0060 (7)	0.0046 (7)
C9	0.0199 (8)	0.0248 (8)	0.0199 (8)	0.0108 (7)	0.0051 (6)	0.0059 (7)
C10	0.0245 (8)	0.0229 (8)	0.0250 (9)	0.0117 (7)	0.0092 (7)	0.0091 (7)
C11	0.0214 (8)	0.0207 (8)	0.0243 (9)	0.0094 (7)	0.0075 (7)	0.0075 (7)
C12	0.0262 (9)	0.0262 (9)	0.0245 (9)	0.0114 (7)	0.0067 (7)	0.0082 (7)
C13	0.0244 (9)	0.0304 (9)	0.0287 (9)	0.0106 (7)	0.0041 (7)	0.0092 (7)
C14	0.0210 (8)	0.0187 (8)	0.0273 (9)	0.0043 (7)	0.0036 (7)	0.0044 (7)
C15	0.0324 (9)	0.0269 (9)	0.0300 (10)	0.0148 (8)	0.0100 (8)	0.0060 (7)
C16	0.0260 (9)	0.0296 (9)	0.0286 (9)	0.0139 (7)	0.0101 (7)	0.0074 (7)
C17	0.0229 (8)	0.0238 (8)	0.0300 (9)	0.0129 (7)	0.0090 (7)	0.0105 (7)
C18	0.0207 (8)	0.0240 (8)	0.0230 (8)	0.0081 (7)	0.0078 (7)	0.0082 (7)
C19	0.0215 (8)	0.0232 (8)	0.0210 (8)	0.0083 (7)	0.0104 (7)	0.0068 (7)
C20	0.0243 (8)	0.0239 (9)	0.0293 (9)	0.0108 (7)	0.0077 (7)	0.0101 (7)
C21	0.0243 (9)	0.0198 (8)	0.0318 (10)	0.0060 (7)	0.0068 (7)	0.0040 (7)
C22	0.0208 (8)	0.0272 (9)	0.0222 (8)	0.0104 (7)	0.0084 (7)	0.0068 (7)
C23	0.0247 (9)	0.0252 (9)	0.0285 (9)	0.0128 (7)	0.0091 (7)	0.0105 (7)
C24	0.0242 (8)	0.0223 (8)	0.0256 (9)	0.0084 (7)	0.0081 (7)	0.0049 (7)
C25	0.0251 (9)	0.0241 (9)	0.0270 (9)	0.0109 (7)	0.0115 (8)	0.0090 (7)

Geometric parameters (Å, º) top

N1—C2	1.3659 (19)	C12—H12B	0.9900
N1—C9	1.3845 (19)	C13—C14	1.537 (2)
N1—C18	1.4597 (18)	C13—H13A	0.9900
N2—C11	1.4466 (19)	C13—H13B	0.9900
N2—C12	1.4804 (19)	C14—C17	1.507 (2)
N2—C16	1.4825 (19)	C14—C15	1.539 (2)
N3—C25	1.150 (2)	C14—H14	1.0000
O1—C17	1.2280 (18)	C15—C16	1.547 (2)
C2—C3	1.383 (2)	C15—H15A	0.9900
C2—H2	0.9500	C15—H15B	0.9900
C3—C10	1.443 (2)	C16—H16A	0.9900
C3—C4	1.446 (2)	C16—H16B	0.9900
C4—C5	1.396 (2)	C18—C19	1.510 (2)
C4—C9	1.409 (2)	C18—H18A	0.9900
C5—C6	1.380 (2)	C18—H18B	0.9900
C5—H5	0.9500	C19—C24	1.387 (2)
C6—C7	1.401 (2)	C19—C20	1.392 (2)
C6—H6	0.9500	C20—C21	1.384 (2)
C7—C8	1.379 (2)	C20—H20	0.9500
C7—H7	0.9500	C21—C22	1.395 (2)
C8—C9	1.391 (2)	C21—H21	0.9500
C8—H8	0.9500	C22—C23	1.392 (2)
C10—C11	1.342 (2)	C22—C25	1.442 (2)
C10—H10	0.9500	C23—C24	1.384 (2)
C11—C17	1.482 (2)	C23—H23	0.9500
C12—C13	1.549 (2)	C24—H24	0.9500
C12—H12A	0.9900

C2—N1—C9	108.68 (12)	H13A—C13—H13B	108.3
C2—N1—C18	127.10 (13)	C17—C14—C13	107.70 (13)
C9—N1—C18	124.18 (13)	C17—C14—C15	107.79 (13)
C11—N2—C12	108.02 (12)	C13—C14—C15	108.08 (13)
C11—N2—C16	108.35 (11)	C17—C14—H14	111.0
C12—N2—C16	108.05 (12)	C13—C14—H14	111.0
N1—C2—C3	110.60 (14)	C15—C14—H14	111.0
N1—C2—H2	124.7	C14—C15—C16	108.19 (12)
C3—C2—H2	124.7	C14—C15—H15A	110.1
C2—C3—C10	129.90 (14)	C16—C15—H15A	110.1
C2—C3—C4	105.74 (13)	C14—C15—H15B	110.1
C10—C3—C4	124.17 (13)	C16—C15—H15B	110.1
C5—C4—C9	119.08 (14)	H15A—C15—H15B	108.4
C5—C4—C3	133.84 (14)	N2—C16—C15	112.41 (12)
C9—C4—C3	107.03 (13)	N2—C16—H16A	109.1
C6—C5—C4	118.62 (15)	C15—C16—H16A	109.1
C6—C5—H5	120.7	N2—C16—H16B	109.1
C4—C5—H5	120.7	C15—C16—H16B	109.1
C5—C6—C7	121.38 (15)	H16A—C16—H16B	107.9
C5—C6—H6	119.3	O1—C17—C11	124.83 (15)
C7—C6—H6	119.3	O1—C17—C14	124.67 (14)
C8—C7—C6	121.27 (15)	C11—C17—C14	110.51 (13)
C8—C7—H7	119.4	N1—C18—C19	112.15 (12)
C6—C7—H7	119.4	N1—C18—H18A	109.2
C7—C8—C9	117.14 (15)	C19—C18—H18A	109.2
C7—C8—H8	121.4	N1—C18—H18B	109.2
C9—C8—H8	121.4	C19—C18—H18B	109.2
N1—C9—C8	129.54 (14)	H18A—C18—H18B	107.9
N1—C9—C4	107.93 (13)	C24—C19—C20	119.08 (14)
C8—C9—C4	122.50 (15)	C24—C19—C18	120.83 (14)
C11—C10—C3	129.13 (15)	C20—C19—C18	120.07 (13)
C11—C10—H10	115.4	C21—C20—C19	120.97 (14)
C3—C10—H10	115.4	C21—C20—H20	119.5
C10—C11—N2	123.45 (14)	C19—C20—H20	119.5
C10—C11—C17	122.77 (14)	C20—C21—C22	119.17 (15)
N2—C11—C17	113.76 (13)	C20—C21—H21	120.4
N2—C12—C13	111.92 (12)	C22—C21—H21	120.4
N2—C12—H12A	109.2	C23—C22—C21	120.39 (14)
C13—C12—H12A	109.2	C23—C22—C25	119.24 (14)
N2—C12—H12B	109.2	C21—C22—C25	120.35 (14)
C13—C12—H12B	109.2	C24—C23—C22	119.51 (14)
H12A—C12—H12B	107.9	C24—C23—H23	120.2
C14—C13—C12	108.64 (13)	C22—C23—H23	120.2
C14—C13—H13A	110.0	C23—C24—C19	120.82 (14)
C12—C13—H13A	110.0	C23—C24—H24	119.6
C14—C13—H13B	110.0	C19—C24—H24	119.6
C12—C13—H13B	110.0	N3—C25—C22	178.06 (17)

C9—N1—C2—C3	−0.32 (16)	C16—N2—C12—C13	59.45 (16)
C18—N1—C2—C3	−177.95 (13)	N2—C12—C13—C14	−0.11 (18)
N1—C2—C3—C10	174.58 (14)	C12—C13—C14—C17	56.92 (16)
N1—C2—C3—C4	−0.44 (16)	C12—C13—C14—C15	−59.29 (17)
C2—C3—C4—C5	178.37 (16)	C17—C14—C15—C16	−57.07 (16)
C10—C3—C4—C5	3.0 (3)	C13—C14—C15—C16	59.08 (16)
C2—C3—C4—C9	1.02 (16)	C11—N2—C16—C15	57.11 (16)
C10—C3—C4—C9	−174.37 (14)	C12—N2—C16—C15	−59.69 (16)
C9—C4—C5—C6	0.0 (2)	C14—C15—C16—N2	0.19 (18)
C3—C4—C5—C6	−177.08 (15)	C10—C11—C17—O1	−2.1 (2)
C4—C5—C6—C7	1.0 (2)	N2—C11—C17—O1	179.80 (13)
C5—C6—C7—C8	−1.0 (2)	C10—C11—C17—C14	177.55 (14)
C6—C7—C8—C9	0.0 (2)	N2—C11—C17—C14	−0.58 (17)
C2—N1—C9—C8	−176.79 (15)	C13—C14—C17—O1	121.88 (16)
C18—N1—C9—C8	0.9 (2)	C15—C14—C17—O1	−121.72 (16)
C2—N1—C9—C4	0.97 (16)	C13—C14—C17—C11	−57.74 (16)
C18—N1—C9—C4	178.69 (12)	C15—C14—C17—C11	58.66 (16)
C7—C8—C9—N1	178.54 (15)	C2—N1—C18—C19	−122.47 (16)
C7—C8—C9—C4	1.1 (2)	C9—N1—C18—C19	60.24 (18)
C5—C4—C9—N1	−179.04 (12)	N1—C18—C19—C24	42.68 (19)
C3—C4—C9—N1	−1.23 (16)	N1—C18—C19—C20	−135.82 (14)
C5—C4—C9—C8	−1.1 (2)	C24—C19—C20—C21	−2.6 (2)
C3—C4—C9—C8	176.73 (14)	C18—C19—C20—C21	175.96 (14)
C2—C3—C10—C11	−5.1 (3)	C19—C20—C21—C22	1.3 (2)
C4—C3—C10—C11	169.08 (15)	C20—C21—C22—C23	0.9 (2)
C3—C10—C11—N2	2.1 (2)	C20—C21—C22—C25	−177.41 (14)
C3—C10—C11—C17	−175.87 (14)	C21—C22—C23—C24	−1.7 (2)
C12—N2—C11—C10	−119.06 (15)	C25—C22—C23—C24	176.58 (14)
C16—N2—C11—C10	124.13 (15)	C22—C23—C24—C19	0.4 (2)
C12—N2—C11—C17	59.06 (15)	C20—C19—C24—C23	1.7 (2)
C16—N2—C11—C17	−57.76 (16)	C18—C19—C24—C23	−176.82 (14)
C11—N2—C12—C13	−57.57 (16)

Experimental details

Crystal data
Chemical formula	C₂₄H₂₁N₃O
M_r	367.44
Crystal system, space group	Triclinic, P1
Temperature (K)	90
a, b, c (Å)	9.0627 (2), 10.7959 (3), 11.6969 (4)
α, β, γ (°)	99.1571 (13), 106.0935 (14), 113.7908 (14)
V (Å³)	957.16 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.44 × 0.40 × 0.25

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SCALEPACK; Otwinowski & Minor, 1997)
T_min, T_max	0.966, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	20970, 4385, 2935
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.128, 1.04
No. of reflections	4385
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.21

Computer programs: COLLECT (Nonius, 1998), SCALEPACK (Otwinowski & Minor, 1997), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELX97 (Sheldrick, 2008) and local procedures.

Acknowledgements

This investigation was supported by NIH/National Cancer Institute grant PO1 CA104457.

References

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