2,3-Tri­methyl­ene-7,8-di­hydro­pyrrolo­[1,2-a]thieno[2,3-d]pyrimidin-4(6H)-one

Bozorov, K.; Elmuradov, B.; Shakhidoyatov, K.; Aisa, H.A.; Tashkhodjaev, B.

doi:10.1107/S1600536813017935

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1224

doi:10.1107/S1600536813017935

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2,3-Trimethylene-7,8-dihydropyrrolo[1,2-a]thieno[2,3-d]pyrimidin-4(6H)-one

Khurshed Bozorov,^a,^b ^* Burkhon Elmuradov,^a Khusnutdin Shakhidoyatov,^a Haji Akber Aisa ^b and Bakhodir Tashkhodjaev ^a

^aS. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str. 77, Tashkent 100170, Uzbekistan, and ^bXinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Science, Urumqi 830011, People's Republic of China
^*Correspondence e-mail: khurshed-m@mail.ru

(Received 17 June 2013; accepted 28 June 2013; online 10 July 2013)

The title molecule, C₁₂H₁₂N₂OS, is planar, with an r.m.s. deviation of 0.04 Å. In the crystal, the N atom adjacent to the carbonyl group is sp²-hybridized. The crystal structure is stabilized by π–π stacking interactions observed between thiophene and pyrimidinone rings of c-glide-related molecules [centroid–centroid distance = 3.9554 (13) Å] and by C—H⋯π interactions, forming an infinite chain along the c-axis direction.

Related literature

For background information on related compounds, see: Ibrahim et al. (1996 ); Litvinov (2004 ). For the synthesis of the title compound, see: Csukonyi et al. (1986 ); Elmuradov et al. (2011 ). For its physiological activity, see: Lilienkampf et al. (2007 ); Moore et al. (2006 ). For ¹H NMR and IR spectroscopy of the title compound, see: Bozorov et al. (2013 ). For the related structures of the thieno[2,3-d] pyrimidin-4-one derivatives, see; Lilienkampf et al. (2007).

Experimental

Crystal data

C₁₂H₁₂N₂OS
M_r = 232.30
Monoclinic, P 2₁ /c
a = 10.181 (2) Å
b = 12.163 (2) Å
c = 8.8624 (18) Å
β = 100.17 (3)°
V = 1080.2 (4) Å³
Z = 4
Cu Kα radiation
μ = 2.48 mm⁻¹
T = 292 K
0.20 × 0.17 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur Ruby diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.639, T_max = 0.689
5655 measured reflections
2225 independent reflections
1874 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.124
S = 1.06
2225 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the S1/C2/C3/C3A/C9A (thiophene) and C3A/C4/N5/C8A/N9/C9A rings

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6B⋯Cg2ⁱ	0.97	2.85	3.770 (2)	159
C10—H10B⋯Cg1ⁱⁱ	0.97	2.95	3.735 (2)	139
Symmetry codes: (i) -x, -y+1, -z; (ii) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: SHELXTL, PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813017935/pk2490sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813017935/pk2490Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813017935/pk2490Isup3.cml

checkCIF report

Comment top

Thieno[2,3-d]pyrimidin-4-ones (Litvinov, 2004; Ibrahim, et al., 1996) are a large group of heterocyclic compounds. These compounds and their derivatives possess different pharmacological activities (Lilienkampf, et al., 2007; Moore, et al., 2006).

Interaction of ethyl 2-amino-4,5-trimethylene-thiophene-3-carboxylate with γ-butyrolactam in presence of phosphorus oxycloride leads to the formation of a new potentially active tetracyclic thieno[2,3-d] pyrimidin-4-one. Synthesis of the title compound was carried out at 368-371 K with reagents in the ratio ester:lactam:POCl₃ of 1:1.5:3.6. The structure of the synthesized compound has been investigated by XRD analysis.

The molecular structure of the title compound is shown in Fig. 2. As shown in the picture, the molecule of the title compound is planar with r.m.s. deviation of 0.04 Å (non-hydrogen atoms). The sum of bond angles of atom N5 (close to 360°) and bond lengths indicate sp² hybridization of the nitrogen atom. This indicates that the lone electron pair of N5 atom participates in a conjugation with π-electrons of carbonyl group (C4═O1).

The crystal structure is stabilized by π-π interactions between neighboring molecules Cg1···Cg2 [Cg1 and Cg2 are centroids of the S1/C2/C3/C3A/C9A (thiophene) and C3A/C4/N5/C8A/N9/C9A rings]. With the distance Cg1···Cg2ⁱ of 3.9554 (13) Å [symmetry code: (i) x, 1/2 - y, 1/2 + z] (Spek, 2009). In addition, intermolecular C6–H···Cg2 and C10–H···Cg1 interactions are present (Table 1).

Related literature top

For background information on related compounds, see: Ibrahim et al. (1996); Litvinov (2004). For the synthesis of the title compound, see: Csukonyi et al. (1986); Elmuradov et al. (2011). For its physiological activity, see: Lilienkampf et al. (2007); Moore et al. (2006). For ¹H NMR and IR spectroscopy of the title compound, see: Bozorov et al. (2013). For the related structures of the thieno[2,3-d] pyrimidin-4-one derivatives, see; Lilienkampf et al. (2007).

Experimental top

The title compound was synthesized on the basis of a well-known method (Elmuradov, et al., 2011) (Fig. 2). Light yellow crystals suitable for X-ray analysis (in the form of prisms with size 0.20x0.17x0.15 mm) were obtained from DMSO solvent at room temperature, m.p. 475-476 K.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); 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: SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Reaction scheme for the formation of the title compound.

15-Thia-2,7-diazatetracyclo[7.6.0.0^3,7.0^10,14]pentadeca-1(9),2,10 (14)-trien-8-one top

Crystal data top

C₁₂H₁₂N₂OS	F(000) = 488
M_r = 232.30	D_x = 1.428 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 475(1) K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54184 Å
a = 10.181 (2) Å	Cell parameters from 3341 reflections
b = 12.163 (2) Å	θ = 3.6–75.5°
c = 8.8624 (18) Å	µ = 2.48 mm⁻¹
β = 100.17 (3)°	T = 292 K
V = 1080.2 (4) Å³	Prismatic, light yellow
Z = 4	0.20 × 0.17 × 0.15 mm

Data collection top

Oxford Diffraction Xcalibur Ruby diffractometer	2225 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1874 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Detector resolution: 10.2576 pixels mm^-1	θ_max = 75.7°, θ_min = 4.4°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −15→14
T_min = 0.639, T_max = 0.689	l = −9→11
5655 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0783P)² + 0.1555P] where P = (F_o² + 2F_c²)/3
2225 reflections	(Δ/σ)_max < 0.001
145 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₂H₁₂N₂OS	V = 1080.2 (4) Å³
M_r = 232.30	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 10.181 (2) Å	µ = 2.48 mm⁻¹
b = 12.163 (2) Å	T = 292 K
c = 8.8624 (18) Å	0.20 × 0.17 × 0.15 mm
β = 100.17 (3)°

Data collection top

Oxford Diffraction Xcalibur Ruby diffractometer	2225 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	1874 reflections with I > 2σ(I)
T_min = 0.639, T_max = 0.689	R_int = 0.022
5655 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.06	Δρ_max = 0.25 e Å⁻³
2225 reflections	Δρ_min = −0.20 e Å⁻³
145 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.

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

	x	y	z	U_iso*/U_eq
S1	0.30220 (5)	0.15857 (4)	0.11554 (6)	0.05357 (19)
O1	0.23418 (14)	0.55482 (10)	−0.02313 (17)	0.0605 (4)
N5	0.08460 (14)	0.42802 (12)	−0.13884 (16)	0.0443 (3)
N9	0.09373 (15)	0.23714 (13)	−0.08909 (19)	0.0531 (4)
C2	0.41506 (17)	0.25495 (15)	0.2035 (2)	0.0463 (4)
C3	0.38380 (17)	0.35900 (14)	0.15532 (19)	0.0436 (4)
C3A	0.26442 (16)	0.36454 (13)	0.04359 (18)	0.0417 (4)
C4	0.19968 (16)	0.45820 (14)	−0.03696 (19)	0.0439 (4)
C6	0.0044 (2)	0.50792 (17)	−0.2400 (2)	0.0543 (4)
H6A	0.0578	0.5446	−0.3053	0.065*
H6B	−0.0338	0.5627	−0.1810	0.065*
C7	−0.1031 (3)	0.4386 (2)	−0.3334 (3)	0.0831 (8)
H7A	−0.1903	0.4673	−0.3247	0.100*
H7B	−0.0942	0.4403	−0.4405	0.100*
C8	−0.0894 (2)	0.3233 (2)	−0.2749 (3)	0.0686 (6)
H8A	−0.0839	0.2721	−0.3575	0.082*
H8B	−0.1647	0.3033	−0.2272	0.082*
C8A	0.03749 (18)	0.32290 (16)	−0.1596 (2)	0.0485 (4)
C9A	0.20876 (16)	0.26112 (14)	0.0111 (2)	0.0451 (4)
C10	0.5408 (2)	0.24589 (17)	0.3183 (2)	0.0588 (5)
H10A	0.6061	0.2001	0.2806	0.071*
H10B	0.5240	0.2165	0.4148	0.071*
C11	0.5869 (2)	0.36625 (19)	0.3350 (3)	0.0713 (6)
H11A	0.5949	0.3891	0.4411	0.086*
H11B	0.6737	0.3735	0.3052	0.086*
C12	0.4854 (2)	0.43942 (16)	0.2330 (2)	0.0571 (5)
H12A	0.4453	0.4918	0.2938	0.069*
H12B	0.5268	0.4790	0.1587	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0499 (3)	0.0376 (3)	0.0673 (3)	−0.00227 (17)	−0.0058 (2)	0.00621 (18)
O1	0.0616 (8)	0.0397 (7)	0.0736 (9)	−0.0042 (6)	−0.0058 (7)	0.0034 (6)
N5	0.0413 (7)	0.0445 (8)	0.0446 (7)	0.0029 (6)	0.0010 (6)	0.0028 (6)
N9	0.0455 (8)	0.0439 (8)	0.0636 (9)	−0.0057 (6)	−0.0080 (7)	−0.0022 (7)
C2	0.0415 (8)	0.0443 (9)	0.0501 (9)	−0.0001 (7)	−0.0002 (7)	0.0022 (7)
C3	0.0412 (8)	0.0415 (8)	0.0461 (8)	−0.0018 (6)	0.0019 (7)	−0.0006 (7)
C3A	0.0401 (8)	0.0387 (8)	0.0443 (8)	−0.0013 (6)	0.0021 (6)	−0.0012 (7)
C4	0.0425 (8)	0.0412 (8)	0.0459 (9)	−0.0004 (6)	0.0024 (6)	0.0003 (7)
C6	0.0516 (9)	0.0579 (11)	0.0499 (9)	0.0109 (8)	−0.0002 (7)	0.0097 (8)
C7	0.0787 (16)	0.0799 (18)	0.0743 (15)	−0.0024 (13)	−0.0312 (12)	0.0092 (13)
C8	0.0481 (11)	0.0695 (14)	0.0780 (14)	−0.0021 (9)	−0.0167 (10)	−0.0014 (11)
C8A	0.0404 (8)	0.0516 (10)	0.0501 (9)	−0.0021 (7)	−0.0011 (7)	−0.0034 (7)
C9A	0.0420 (8)	0.0392 (8)	0.0517 (9)	−0.0009 (7)	0.0013 (7)	0.0002 (7)
C10	0.0482 (10)	0.0584 (12)	0.0631 (11)	0.0020 (8)	−0.0086 (8)	0.0058 (9)
C11	0.0600 (12)	0.0613 (13)	0.0799 (14)	−0.0044 (10)	−0.0226 (11)	0.0019 (11)
C12	0.0504 (10)	0.0495 (10)	0.0640 (11)	−0.0065 (8)	−0.0101 (8)	−0.0023 (8)

Geometric parameters (Å, º) top

S1—C2	1.7278 (18)	C6—H6B	0.9700
S1—C9A	1.7339 (18)	C7—C8	1.493 (3)
O1—C4	1.226 (2)	C7—H7A	0.9700
N5—C8A	1.367 (2)	C7—H7B	0.9700
N5—C4	1.396 (2)	C8—C8A	1.499 (2)
N5—C6	1.468 (2)	C8—H8A	0.9700
N9—C8A	1.296 (2)	C8—H8B	0.9700
N9—C9A	1.371 (2)	C10—C11	1.536 (3)
C2—C3	1.355 (2)	C10—H10A	0.9700
C2—C10	1.492 (2)	C10—H10B	0.9700
C3—C3A	1.427 (2)	C11—C12	1.532 (3)
C3—C12	1.500 (2)	C11—H11A	0.9700
C3A—C9A	1.389 (2)	C11—H11B	0.9700
C3A—C4	1.441 (2)	C12—H12A	0.9700
C6—C7	1.508 (3)	C12—H12B	0.9700
C6—H6A	0.9700

C2—S1—C9A	90.63 (9)	C7—C8—H8A	110.8
C8A—N5—C4	124.57 (15)	C8A—C8—H8A	110.8
C8A—N5—C6	113.15 (15)	C7—C8—H8B	110.8
C4—N5—C6	122.23 (16)	C8A—C8—H8B	110.8
C8A—N9—C9A	113.28 (15)	H8A—C8—H8B	108.9
C3—C2—C10	114.15 (16)	N9—C8A—N5	125.00 (16)
C3—C2—S1	113.02 (13)	N9—C8A—C8	125.83 (17)
C10—C2—S1	132.81 (14)	N5—C8A—C8	109.16 (16)
C2—C3—C3A	112.72 (15)	N9—C9A—C3A	126.71 (15)
C2—C3—C12	111.10 (15)	N9—C9A—S1	121.22 (13)
C3A—C3—C12	136.18 (16)	C3A—C9A—S1	112.07 (12)
C9A—C3A—C3	111.55 (14)	C2—C10—C11	101.88 (15)
C9A—C3A—C4	118.64 (15)	C2—C10—H10A	111.4
C3—C3A—C4	129.80 (15)	C11—C10—H10A	111.4
O1—C4—N5	120.62 (16)	C2—C10—H10B	111.4
O1—C4—C3A	127.61 (16)	C11—C10—H10B	111.4
N5—C4—C3A	111.77 (15)	H10A—C10—H10B	109.3
N5—C6—C7	103.66 (17)	C12—C11—C10	109.51 (16)
N5—C6—H6A	111.0	C12—C11—H11A	109.8
C7—C6—H6A	111.0	C10—C11—H11A	109.8
N5—C6—H6B	111.0	C12—C11—H11B	109.8
C7—C6—H6B	111.0	C10—C11—H11B	109.8
H6A—C6—H6B	109.0	H11A—C11—H11B	108.2
C8—C7—C6	108.70 (17)	C3—C12—C11	103.34 (16)
C8—C7—H7A	109.9	C3—C12—H12A	111.1
C6—C7—H7A	109.9	C11—C12—H12A	111.1
C8—C7—H7B	109.9	C3—C12—H12B	111.1
C6—C7—H7B	109.9	C11—C12—H12B	111.1
H7A—C7—H7B	108.3	H12A—C12—H12B	109.1
C7—C8—C8A	104.84 (17)

C9A—S1—C2—C3	−0.38 (15)	C9A—N9—C8A—N5	−0.2 (3)
C9A—S1—C2—C10	−178.7 (2)	C9A—N9—C8A—C8	−179.6 (2)
C10—C2—C3—C3A	178.91 (16)	C4—N5—C8A—N9	−0.8 (3)
S1—C2—C3—C3A	0.3 (2)	C6—N5—C8A—N9	176.90 (19)
C10—C2—C3—C12	−0.5 (2)	C4—N5—C8A—C8	178.62 (17)
S1—C2—C3—C12	−179.19 (14)	C6—N5—C8A—C8	−3.7 (2)
C2—C3—C3A—C9A	0.0 (2)	C7—C8—C8A—N9	−174.1 (2)
C12—C3—C3A—C9A	179.3 (2)	C7—C8—C8A—N5	6.5 (3)
C2—C3—C3A—C4	−178.74 (17)	C8A—N9—C9A—C3A	1.6 (3)
C12—C3—C3A—C4	0.5 (4)	C8A—N9—C9A—S1	−178.89 (14)
C8A—N5—C4—O1	−178.76 (18)	C3—C3A—C9A—N9	179.23 (17)
C6—N5—C4—O1	3.7 (3)	C4—C3A—C9A—N9	−1.8 (3)
C8A—N5—C4—C3A	0.6 (2)	C3—C3A—C9A—S1	−0.3 (2)
C6—N5—C4—C3A	−176.96 (15)	C4—C3A—C9A—S1	178.60 (12)
C9A—C3A—C4—O1	179.91 (18)	C2—S1—C9A—N9	−179.18 (16)
C3—C3A—C4—O1	−1.4 (3)	C2—S1—C9A—C3A	0.40 (14)
C9A—C3A—C4—N5	0.6 (2)	C3—C2—C10—C11	−0.4 (3)
C3—C3A—C4—N5	179.35 (17)	S1—C2—C10—C11	177.87 (17)
C8A—N5—C6—C7	−0.8 (2)	C2—C10—C11—C12	1.2 (3)
C4—N5—C6—C7	177.02 (18)	C2—C3—C12—C11	1.3 (2)
N5—C6—C7—C8	4.9 (3)	C3A—C3—C12—C11	−178.0 (2)
C6—C7—C8—C8A	−6.9 (3)	C10—C11—C12—C3	−1.5 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the S1/C2/C3/C3A/C9A (thiophene) and C3A/C4/N5/C8A/N9/C9A rings

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6B···Cg2ⁱ	0.97	2.85	3.770 (2)	159
C10—H10B···Cg1ⁱⁱ	0.97	2.95	3.735 (2)	139

Symmetry codes: (i) −x, −y+1, −z; (ii) x, −y−1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₂N₂OS
M_r	232.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	292
a, b, c (Å)	10.181 (2), 12.163 (2), 8.8624 (18)
β (°)	100.17 (3)
V (Å³)	1080.2 (4)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	2.48
Crystal size (mm)	0.20 × 0.17 × 0.15

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.639, 0.689
No. of measured, independent and observed [I > 2σ(I)] reflections	5655, 2225, 1874
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.124, 1.06
No. of reflections	2225
No. of parameters	145
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.20

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the S1/C2/C3/C3A/C9A (thiophene) and C3A/C4/N5/C8A/N9/C9A rings

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6B···Cg2ⁱ	0.97	2.85	3.770 (2)	159
C10—H10B···Cg1ⁱⁱ	0.97	2.95	3.735 (2)	139

Symmetry codes: (i) −x, −y+1, −z; (ii) x, −y−1/2, z−1/2.

Acknowledgements

We thank the Academy of Sciences of the Republic of Uzbekistan for supporting this study (grants FA-F7-T185 and FA-F7-T207), and the project supported by the Funds for International Cooperation and Exchange of the National Natural Science Foundation of China (grant No. 31110103908).

References

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