(E)-3-[4-(Dimethyl­amino)­benzyl­idene]-2,3-di­hydro-1H,9H-pyrrolo­[2,1-b]quinazolin-9-one

Elmuradov, B.Z.; Okmanov, R.Y.; Abdurazakov, A.S.; Tashkhodjaev, B.; Shakhidoyatov, K.M.

doi:10.1107/S1600536810020878

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1592

doi:10.1107/S1600536810020878

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(E)-3-[4-(Dimethylamino)benzylidene]-2,3-dihydro-1H,9H-pyrrolo[2,1-b]quinazolin-9-one

Burkhon Zh. Elmuradov,^a ^* Rasul Ya. Okmanov,^a Asqar Sh. Abdurazakov,^a Bakhodir Tashkhodjaev ^a and Khusnutdin M. Shakhidoyatov ^a

^aS. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str. 77, Tashkent 100170, Uzbekistan
^*Correspondence e-mail: burkhon@rambler.ru

(Received 18 May 2010; accepted 1 June 2010; online 5 June 2010)

The title compound, C₂₀H₁₉N₃O, was obtained by condensation of 2,3-dihydro-1H,9H-pyrrolo[2,1-b]quinazolin-9-one (alkaloid deoxyvasicinone, isolated from Peganum Harmala) with 4-(dimethylamino)benzaldehyde in the presence of sodium methoxide. The 2,3-dihydro-1H,9H-pyrrolo[2,1-b]quinazolin-9-one part of the molecule is roughly planar (r.m.s. deviation = 0.0178 Å) and is essentially coplanar with the benzilidene ring (r.m.s. deviation = 0.0080 Å), forming a dihedral angle of 5.0 (1)°. The crystal structure is stabilized by two aromatic π–π stacking interactions observed between the benzene rings of neighboring molecules [centroid–centroid distance = 3.7555 (19) Å.

Related literature

For the synthesis of 2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one and the title compound, see: Shakhidoyatov et al. (1977 ); Elmuradov et al. (2009 ); Shakhidoyatov & Kaysarov, (1998 ); Jahng et al. (2008 ). For the physiological activity of 2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one and its derivatives, see: Chatterjee & Ganguly, (1968 ); Al-Shamma et al. (1981 ); Johne (1981 ); Telezhenetskaya & Yunusov, (1977 ); Yunusov et al. (1978 ). For related structures, see: Barnes et al. (1985 ); Wu et al. (1997 ).

Experimental

Crystal data

C₂₀H₁₉N₃O
M_r = 317.38
Monoclinic, P 2₁ /c
a = 8.8030 (18) Å
b = 16.415 (3) Å
c = 11.463 (2) Å
β = 105.05 (3)°
V = 1599.6 (6) Å³
Z = 4
Cu Kα radiation
μ = 0.66 mm⁻¹
T = 300 K
0.60 × 0.20 × 0.15 mm

Data collection

Stoe Stadi-4 four-circle diffractometer
Absorption correction: ψ scan (X-RED; Stoe & Cie, 1997 ). T_min = 0.854, T_max = 0.906
2446 measured reflections
2342 independent reflections
1728 reflections with I > 2σ(I)
θ_max = 60.0°
3 standard reflections every 60 min intensity decay: 10.0%

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.142
S = 1.13
2342 reflections
220 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: STADI4 (Stoe & Cie, 1997); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 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: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810020878/si2264sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810020878/si2264Isup2.hkl

checkCIF report

Comment top

The derivatives of tricyclic quinazoline alkaloids possess different pharmacological activities (Chatterjee & Ganguly, 1968; Al-Shamma et al., 1981; Johne, 1981; Telezhenetskaya & Yunusov, 1977; Yunusov et al., 1978) and was found simples and convenient methods of a synthesis of these compounds (Shakhidoyatov et al., 1977; Shakhidoyatov & Kaysarov, 1998; Jahng et al., 2008).

Condensation of 2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one (alkaloid Deoxyvasicinone, isolated from Peganum Harmala) (Chatterjee & Ganguly, 1968) with 4-dimethylaminobenzaldehyde at 278 (1) K in presence of sodium methoxide (Elmuradov et al., 2009) leads to the formation of (E)-3-(4-dimethylamino)benzylidene-2,3-dihydro- 1H-pyrrolo[2,1-b]quinazolin-9-one (Figure 1).

The quinazoline part of molecule (C1/C2/C3/C3a/N4/C4a/C5/C6/C7/C8/C8a/C9/N10) is flat, r.m.s. deviation = 0.0178 Å, and benzilidene ring (C1'/C2'/C3'/C4'/C5'/C6'/C7') is also flat, r.m.s. deviation = 0.0080 Å, the angle between fragment planes is 5.0 (1)° (Figure 2). Torsion angle in fragment C3a–C3–C7'–C6' is 175.0 (5)° (Barnes et al., 1985; Wu et al., 1997), indicating the conjugation of π-electronic systems of pyrrolo(2,1-b)quinazolone and benzilidene rings. The sum of valent angles of all nitrogen atoms are close to 360° (Figure 3) which specifies sp² hybridizations of nitrogen atoms. It specifies, that the lone electronic pair of nitrogen atoms participate in a conjugation with π electrons of aromatic ring. The crystal structure is stabilized by π-π interactions between the benzene rings of neighbor standing molecules with the distance Cg3···Cg4ⁱ = 3.7555 (19) Å [symmetry code: (i) -x, 1 - y, 1 - z; Cg3 and Cg4 are centroid of the C1'-C6' and C4a/C5-C8/C8a two benzene rings].

Related literature top

For the synthesis of 2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one and the title compound, see: Shakhidoyatov et al. (1977); Elmuradov et al. (2009); Shakhidoyatov & Kaysarov, (1998); Jahng et al. (2008). For the physiological activity of 2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one and its derivatives, see: Chatterjee & Ganguly, (1968); Al-Shamma et al. (1981); Johne (1981); Telezhenetskaya & Yunusov, (1977); Yunusov et al. (1978). For related structures, see: Barnes et al. (1985); Wu et al. (1997).

Experimental top

0.115 g sodium (5 mmole) was dissolved in 5 ml absolute methanol, and 0.186 g (1 mmole) of 2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one and 0.151 g (1 mmole) 4-dimethylamino-benzaldehyde were added (Figure 1). Reaction mixture was left at 278 (1) K for 3 weeks. The dropped out single crystals, suitable for X-ray analysis were filtered, flushed at first with alcohol, then water. 0.05 g (16%) of the title compound was obtained in the reaction, m.p. 514-516 K.

Computing details top

Data collection: STADI4 (Stoe & Cie, 1997); cell refinement: STADI4 (Stoe & Cie, 1997); data reduction: X-RED (Stoe & Cie, 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: SHELXL97 and PLATON (Spek, 2009).

Figures top

	Fig. 1. Reaction sequence.
	Fig. 2. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 3. A section of molecular packing of the title compound.

(E)-3-[4-(Dimethylamino)benzylidene]-2,3-dihydro- 1H,9H-pyrrolo[2,1-b]quinazolin-9-one top

Crystal data top

C₂₀H₁₉N₃O	F(000) = 672
M_r = 317.38	D_x = 1.318 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 514(2) K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54184 Å
a = 8.8030 (18) Å	Cell parameters from 12 reflections
b = 16.415 (3) Å	θ = 10–20°
c = 11.463 (2) Å	µ = 0.66 mm⁻¹
β = 105.05 (3)°	T = 300 K
V = 1599.6 (6) Å³	Prizmatic, light yellow
Z = 4	0.60 × 0.20 × 0.15 mm

Data collection top

Stoe Stadi-4 four-circle diffractometer	1728 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.000
Graphite monochromator	θ_max = 60.0°, θ_min = 4.8°
Scan width (ω) = 1.32 – 1.56, scan ratio 2θ:ω = 0.00 I(Net) and sigma(I) calculated according to Blessing (1987)	h = −9→9
Absorption correction: ψ scan (X-RED; Stoe & Cie, 1997).	k = 0→18
T_min = 0.854, T_max = 0.906	l = 0→12
2446 measured reflections	3 standard reflections every 60 min
2342 independent reflections	intensity decay: 10.0%

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)] = 0.057	H-atom parameters constrained
wR(F²) = 0.142	w = 1/[σ²(F_o²) + (0.0446P)² + 1.0639P] where P = (F_o² + 2F_c²)/3
S = 1.13	(Δ/σ)_max < 0.001
2342 reflections	Δρ_max = 0.16 e Å⁻³
220 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0033 (3)

Crystal data top

C₂₀H₁₉N₃O	V = 1599.6 (6) Å³
M_r = 317.38	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 8.8030 (18) Å	µ = 0.66 mm⁻¹
b = 16.415 (3) Å	T = 300 K
c = 11.463 (2) Å	0.60 × 0.20 × 0.15 mm
β = 105.05 (3)°

Data collection top

Stoe Stadi-4 four-circle diffractometer	1728 reflections with I > 2σ(I)
Absorption correction: ψ scan (X-RED; Stoe & Cie, 1997).	R_int = 0.000
T_min = 0.854, T_max = 0.906	θ_max = 60.0°
2446 measured reflections	3 standard reflections every 60 min
2342 independent reflections	intensity decay: 10.0%

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.142	H-atom parameters constrained
S = 1.13	Δρ_max = 0.16 e Å⁻³
2342 reflections	Δρ_min = −0.18 e Å⁻³
220 parameters

Special details top

Experimental. Empirical absorption correction using ψ Scan. Reflections used Mu * R = 0.00

H K L, θ, χ, I~min~/I~max~: -2 1 1 21.1 80.5 0.900

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.

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

	x	y	z	U_iso*/U_eq
O1	−0.1964 (3)	0.57316 (13)	0.07780 (19)	0.0553 (7)
C1	0.0365 (4)	0.48250 (18)	0.2373 (3)	0.0496 (9)
H1A	0.0818	0.4880	0.1691	0.060*
H1B	−0.0432	0.4402	0.2197	0.060*
C2	0.1634 (4)	0.46318 (18)	0.3530 (3)	0.0435 (8)
H2A	0.1435	0.4107	0.3851	0.052*
H2B	0.2663	0.4617	0.3370	0.052*
C3	0.1562 (3)	0.52982 (17)	0.4410 (3)	0.0373 (7)
C3A	0.0343 (3)	0.58741 (17)	0.3798 (2)	0.0355 (7)
N4	−0.0078 (3)	0.65349 (14)	0.4246 (2)	0.0391 (6)
C4A	−0.1278 (3)	0.69758 (17)	0.3470 (3)	0.0378 (7)
C5	−0.1799 (4)	0.76888 (18)	0.3914 (3)	0.0459 (8)
H5A	−0.1330	0.7856	0.4700	0.055*
C6	−0.2995 (4)	0.8144 (2)	0.3201 (3)	0.0495 (8)
H6A	−0.3327	0.8618	0.3503	0.059*
C7	−0.3707 (4)	0.78958 (19)	0.2026 (3)	0.0476 (8)
H7A	−0.4525	0.8201	0.1549	0.057*
C8	−0.3213 (3)	0.72058 (19)	0.1568 (3)	0.0452 (8)
H8A	−0.3690	0.7047	0.0780	0.054*
C8A	−0.1995 (3)	0.67373 (17)	0.2279 (3)	0.0379 (7)
C9	−0.1474 (3)	0.59996 (18)	0.1804 (3)	0.0413 (7)
N10	−0.0298 (3)	0.55973 (14)	0.2639 (2)	0.0384 (6)
N1'	0.7209 (3)	0.34893 (18)	0.8577 (2)	0.0585 (8)
C1'	0.3643 (3)	0.49063 (17)	0.6292 (2)	0.0375 (7)
C2'	0.4284 (4)	0.42189 (18)	0.5885 (3)	0.0445 (8)
H2'A	0.3902	0.4064	0.5081	0.053*
C3'	0.5455 (4)	0.37605 (19)	0.6621 (3)	0.0451 (8)
H3'A	0.5847	0.3310	0.6303	0.054*
C4'	0.6065 (3)	0.39601 (18)	0.7836 (3)	0.0426 (8)
C5'	0.5453 (4)	0.46547 (19)	0.8262 (3)	0.0462 (8)
H5'A	0.5839	0.4812	0.9064	0.055*
C6'	0.4282 (3)	0.51068 (18)	0.7500 (3)	0.0423 (8)
H6'A	0.3904	0.5566	0.7808	0.051*
C7'	0.2395 (3)	0.54038 (17)	0.5554 (3)	0.0383 (7)
H7'A	0.2135	0.5864	0.5934	0.046*
C8'	0.7668 (5)	0.3632 (3)	0.9855 (3)	0.0906 (15)
H8'A	0.6753	0.3623	1.0164	0.136*
H8'B	0.8171	0.4154	1.0015	0.136*
H8'C	0.8386	0.3214	1.0243	0.136*
C9'	0.7788 (4)	0.2766 (2)	0.8122 (3)	0.0617 (10)
H9'A	0.8256	0.2912	0.7482	0.093*
H9'B	0.6932	0.2397	0.7818	0.093*
H9'C	0.8562	0.2509	0.8762	0.093*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0632 (15)	0.0588 (14)	0.0371 (13)	0.0057 (12)	0.0006 (11)	−0.0039 (11)
C1	0.056 (2)	0.0412 (18)	0.0468 (19)	0.0081 (16)	0.0043 (16)	−0.0075 (15)
C2	0.0460 (18)	0.0406 (18)	0.0415 (17)	0.0033 (15)	0.0072 (15)	−0.0009 (14)
C3	0.0345 (16)	0.0388 (16)	0.0379 (16)	−0.0011 (13)	0.0079 (13)	0.0008 (13)
C3A	0.0346 (16)	0.0360 (16)	0.0353 (15)	−0.0039 (13)	0.0079 (13)	−0.0016 (13)
N4	0.0348 (14)	0.0373 (14)	0.0418 (14)	0.0027 (11)	0.0039 (11)	−0.0016 (11)
C4A	0.0363 (17)	0.0348 (16)	0.0427 (17)	−0.0020 (13)	0.0111 (14)	0.0033 (13)
C5	0.0415 (18)	0.0440 (19)	0.0507 (19)	0.0007 (15)	0.0093 (15)	−0.0026 (15)
C6	0.0465 (19)	0.0432 (18)	0.059 (2)	0.0066 (15)	0.0149 (17)	0.0039 (16)
C7	0.0395 (18)	0.0464 (19)	0.057 (2)	0.0056 (15)	0.0124 (15)	0.0178 (16)
C8	0.0378 (17)	0.0506 (19)	0.0455 (18)	0.0015 (15)	0.0079 (14)	0.0109 (15)
C8A	0.0375 (17)	0.0371 (17)	0.0384 (16)	−0.0026 (13)	0.0088 (13)	0.0044 (13)
C9	0.0400 (18)	0.0453 (18)	0.0370 (17)	−0.0056 (14)	0.0072 (14)	0.0017 (14)
N10	0.0401 (14)	0.0368 (14)	0.0356 (13)	0.0023 (11)	0.0051 (11)	−0.0017 (11)
N1'	0.0514 (17)	0.0607 (19)	0.0523 (17)	0.0112 (15)	−0.0062 (14)	0.0008 (14)
C1'	0.0340 (16)	0.0379 (17)	0.0383 (16)	−0.0034 (13)	0.0052 (13)	−0.0011 (13)
C2'	0.0471 (19)	0.0445 (18)	0.0385 (17)	−0.0001 (15)	0.0054 (14)	−0.0029 (14)
C3'	0.0454 (19)	0.0449 (18)	0.0431 (18)	0.0035 (15)	0.0082 (15)	0.0014 (15)
C4'	0.0336 (17)	0.0441 (18)	0.0462 (18)	−0.0052 (14)	0.0033 (14)	0.0058 (15)
C5'	0.0423 (18)	0.0491 (19)	0.0414 (18)	−0.0042 (16)	0.0004 (15)	−0.0028 (15)
C6'	0.0411 (17)	0.0412 (17)	0.0426 (17)	−0.0020 (14)	0.0071 (14)	−0.0046 (14)
C7'	0.0347 (16)	0.0368 (16)	0.0430 (17)	0.0010 (13)	0.0096 (14)	−0.0007 (13)
C8'	0.092 (3)	0.103 (3)	0.056 (2)	0.034 (3)	−0.017 (2)	0.000 (2)
C9'	0.048 (2)	0.055 (2)	0.075 (2)	0.0088 (18)	0.0019 (18)	0.0083 (19)

Geometric parameters (Å, º) top

O1—C9	1.225 (3)	C8A—C9	1.450 (4)
C1—N10	1.461 (4)	C9—N10	1.382 (4)
C1—C2	1.529 (4)	N1'—C4'	1.375 (4)
C1—H1A	0.9700	N1'—C8'	1.434 (4)
C1—H1B	0.9700	N1'—C9'	1.442 (4)
C2—C3	1.500 (4)	C1'—C6'	1.392 (4)
C2—H2A	0.9700	C1'—C2'	1.395 (4)
C2—H2B	0.9700	C1'—C7'	1.452 (4)
C3—C7'	1.338 (4)	C2'—C3'	1.374 (4)
C3—C3A	1.465 (4)	C2'—H2'A	0.9300
C3A—N4	1.295 (3)	C3'—C4'	1.395 (4)
C3A—N10	1.378 (3)	C3'—H3'A	0.9300
N4—C4A	1.394 (4)	C4'—C5'	1.402 (4)
C4A—C5	1.400 (4)	C5'—C6'	1.381 (4)
C4A—C8A	1.403 (4)	C5'—H5'A	0.9300
C5—C6	1.374 (4)	C6'—H6'A	0.9300
C5—H5A	0.9300	C7'—H7'A	0.9300
C6—C7	1.390 (4)	C8'—H8'A	0.9600
C6—H6A	0.9300	C8'—H8'B	0.9600
C7—C8	1.366 (4)	C8'—H8'C	0.9600
C7—H7A	0.9300	C9'—H9'A	0.9600
C8—C8A	1.397 (4)	C9'—H9'B	0.9600
C8—H8A	0.9300	C9'—H9'C	0.9600

N10—C1—C2	103.9 (2)	C3A—N10—C9	123.8 (2)
N10—C1—H1A	111.0	C3A—N10—C1	113.7 (2)
C2—C1—H1A	111.0	C9—N10—C1	122.5 (2)
N10—C1—H1B	111.0	C4'—N1'—C8'	120.5 (3)
C2—C1—H1B	111.0	C4'—N1'—C9'	120.7 (3)
H1A—C1—H1B	109.0	C8'—N1'—C9'	118.2 (3)
C3—C2—C1	106.4 (2)	C6'—C1'—C2'	115.5 (3)
C3—C2—H2A	110.4	C6'—C1'—C7'	119.7 (3)
C1—C2—H2A	110.4	C2'—C1'—C7'	124.8 (3)
C3—C2—H2B	110.4	C3'—C2'—C1'	122.8 (3)
C1—C2—H2B	110.4	C3'—C2'—H2'A	118.6
H2A—C2—H2B	108.6	C1'—C2'—H2'A	118.6
C7'—C3—C3A	122.2 (3)	C2'—C3'—C4'	121.1 (3)
C7'—C3—C2	130.2 (3)	C2'—C3'—H3'A	119.4
C3A—C3—C2	107.6 (2)	C4'—C3'—H3'A	119.4
N4—C3A—N10	124.8 (3)	N1'—C4'—C3'	121.0 (3)
N4—C3A—C3	126.9 (3)	N1'—C4'—C5'	121.8 (3)
N10—C3A—C3	108.3 (2)	C3'—C4'—C5'	117.1 (3)
C3A—N4—C4A	115.4 (2)	C6'—C5'—C4'	120.5 (3)
N4—C4A—C5	117.9 (3)	C6'—C5'—H5'A	119.8
N4—C4A—C8A	123.4 (3)	C4'—C5'—H5'A	119.8
C5—C4A—C8A	118.7 (3)	C5'—C6'—C1'	123.0 (3)
C6—C5—C4A	120.7 (3)	C5'—C6'—H6'A	118.5
C6—C5—H5A	119.6	C1'—C6'—H6'A	118.5
C4A—C5—H5A	119.6	C3—C7'—C1'	129.6 (3)
C5—C6—C7	120.0 (3)	C3—C7'—H7'A	115.2
C5—C6—H6A	120.0	C1'—C7'—H7'A	115.2
C7—C6—H6A	120.0	N1'—C8'—H8'A	109.5
C8—C7—C6	120.4 (3)	N1'—C8'—H8'B	109.5
C8—C7—H7A	119.8	H8'A—C8'—H8'B	109.5
C6—C7—H7A	119.8	N1'—C8'—H8'C	109.5
C7—C8—C8A	120.3 (3)	H8'A—C8'—H8'C	109.5
C7—C8—H8A	119.8	H8'B—C8'—H8'C	109.5
C8A—C8—H8A	119.8	N1'—C9'—H9'A	109.5
C8—C8A—C4A	119.8 (3)	N1'—C9'—H9'B	109.5
C8—C8A—C9	120.7 (3)	H9'A—C9'—H9'B	109.5
C4A—C8A—C9	119.5 (3)	N1'—C9'—H9'C	109.5
O1—C9—N10	120.5 (3)	H9'A—C9'—H9'C	109.5
O1—C9—C8A	126.4 (3)	H9'B—C9'—H9'C	109.5
N10—C9—C8A	113.1 (3)

Experimental details

Crystal data
Chemical formula	C₂₀H₁₉N₃O
M_r	317.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	300
a, b, c (Å)	8.8030 (18), 16.415 (3), 11.463 (2)
β (°)	105.05 (3)
V (Å³)	1599.6 (6)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.66
Crystal size (mm)	0.60 × 0.20 × 0.15

Data collection
Diffractometer	Stoe Stadi-4 four-circle diffractometer
Absorption correction	ψ scan (X-RED; Stoe & Cie, 1997).
T_min, T_max	0.854, 0.906
No. of measured, independent and observed [I > 2σ(I)] reflections	2446, 2342, 1728
R_int	0.000
θ_max (°)	60.0
(sin θ/λ)_max (Å⁻¹)	0.562

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.142, 1.13
No. of reflections	2342
No. of parameters	220
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.18

Computer programs: STADI4 (Stoe & Cie, 1997), X-RED (Stoe & Cie, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXL97 and PLATON (Spek, 2009).

Acknowledgements

We thank the Academy of Sciences of the Republic of Uzbekistan for supporting this study (grant FA-F3-T047).

References

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