Crystal structure of (E)-9-(4-nitro­benzyl­idene)-8,9-di­hydro­pyrido[2,3-d]pyrrolo­[1,2-a]pyrimidin-5(7H)-one

Khodjaniyazov, Kh.U.; Ashurov, J.M.

doi:10.1107/S2056989016003583

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ISSN: 2056-9890

Volume 72| Part 4| April 2016| Pages 452-455

https://doi.org/10.1107/S2056989016003583

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Crystal structure of (E)-9-(4-nitrobenzylidene)-8,9-dihydropyrido[2,3-d]pyrrolo[1,2-a]pyrimidin-5(7H)-one

Khamid U. Khodjaniyazov ^a ^* and Jamshid M. Ashurov ^b

^aS. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str. 77, Tashkent 100170, Uzbekistan, and ^bA. S. Sadikov Institute of Bioorganic Chemistry, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str. 83, Tashkent 100125, Uzbekistan
^*Correspondence e-mail: hamidkhodjaniyazov@yandex.ru

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 24 February 2016; accepted 1 March 2016; online 4 March 2016)

The title compound, C₁₇H₁₂N₄O₃, a pyridopyrrolopyrimidine derivative, is almost planar. The nitrobenzene ring is inclined to the mean plane of the 8,9-dihydropyrido[2,3-d]pyrrolo[1,2-a]pyrimidin-5(7H)-one moiety (r.m.s. deviation = 0.023 Å) by 6.8 (1)°. In the crystal, molecules are linked via C—H⋯O and C—H⋯N hydrogen bonds, forming layers parallel to (101).

Keywords: crystal structure; pyridopyrimidine; pyridopyrrolopyrimidine; 4-nitrobenzaldehyde; ylidene derivative; hydrogen bonding.

CCDC reference: 1456732

1. Chemical context

Pyrido[2,3-d]pyrimidines, and their derivatives, are an important group of heterocyclic compounds that exhibit biological and pharmacological activities. For example, Le Corre et al. (2010 ) have produced a library of pyrido[2,3-d]pyrimidines designed as inhibitors of FGFR3 tyrosine kinase. Ramana Reddy et al. (2014 ) have shown that such compounds are potent inhibitors of cyclin-dependent Kinase 4 (CDK4) and AMPK-related Kinase 5 (ARK5). A series of pyrazolo [4,3-d]pyrimidin-7-ones were synthesizied to study their pyrido kinases (CDKs) inhibitory activities (Geffken et al. 2011 ). The antitumor activity of some new pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidin-5-one derivatives have also been studied (El-Nassan, 2011 ), and the antitumor activity of pyrido[2,3-d]pyrimidine and pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidine derivatives that induce apoptosis through G1 cell-cycle arrest have been reported on by Fares et al. (2014 ). The above observations prompted us to synthesize the title compound, which contains a pyrido[2,3-d]pyrimidin-4-one moiety, and we report herein on its crystal structure.

2. Structural commentary

In the molecular structure of the title compound (Fig. 1), the three fused rings of the 8,9-dihydropyrido[2,3-d]pyrrolo[1,2-a]pyrimidin-5(7H)-one moiety (N1–N3/C1–C10), are essentially planar (r.m.s. deviation = 0.023 Å), with the maximum deviation from the mean plane being 0.036 (2) Å for atom C8. The nitrobenzene ring (C12–C17) is inclined to this mean plane by 6.8 (1)°, while the nitro group (N4/O2/O3) is inclined to the benzene ring by 15.0 (3)°.

Figure 1
Molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

3. Supramolecular features

In the crystal, molecules are linked via C—H⋯O and C—H⋯N hydrogen bonds, forming layers lying parallel to (101); see Fig. 2 and Table 1. Within the layers there are R₂²(7), R₃³(17), and R₃³(21) graph-set motifs present (Fig. 2). The layers are separated by an average interplanar distance of ca 3.4 Å, but there are no significant interlayer interactions present (Fig. 3).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N3ⁱ	0.93	2.58	3.292 (3)	133
C4—H4⋯N1ⁱ	0.93	2.57	3.480 (3)	166
C13—H13⋯O3ⁱⁱ	0.93	2.51	3.363 (3)	153
C16—H16⋯O1ⁱⁱⁱ	0.93	2.45	3.259 (3)	145
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x, y+1, z.

Figure 2
A view along the a axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1

). For clarity, H atoms not involved in hydrogen bonding have been omitted.

Figure 3
A view along the b axis of the crystal packing of the title compound. The hydrogen bonds and interplanar distances (of ca 3.4 Å) are shown as dashed lines (see Table 1

). For clarity, H atoms not involved in hydrogen bonding have been omitted.

4. Database survey

A search of the Cambridge Structural Database (Version 5.37, update November 2015; Groom & Allen, 2014 ) was carried out for various substructures (S1 and S2; Fig. 4) resembling the title compound. For substructure S1 (8,9-dihydropyrido[2,3-d]pyrrolo[1,2-a]pyrimidin-5(7H)-one), no hits were obtained. For substructure S2 (4H-3λ2-pyrido[2,3-d]pyrimidin-4-one), seven hits were found. Two of these compounds have substructure S3 (pyrido[2′,3′:4,5]pyrimido[1,2-a]indol-5(11H)-one), viz 9-fluoropyrido[2′,3′:4,5]pyrimido[1,2-a]indole-5,11-dione (refcode NIJYIP; CCDC 269950; Hicks et al., 2005 ), and 9-bromopyrido[2′,3′:4,5]pyrimido[1,2-a]indole-5,11-dione (refcode NIJYOV; CCDC 218226; DiTusa, 2003 ). They are classed as tryptanthrins, which have been shown to have strong antibacterial activity, for example, against malaria (Hicks et al., 2005).

Figure 4
Substructures used for the database survey.

5. Synthesis and crystallization

To a mixture of 2,3-trimethylenepyrido[2,3-d]pyrimidin-4-one (0.094 g, 0.5 mmol) and p-nitrobenzaldehyde (0.094 g, 0.6 mmol) was added acetic acid (3 ml, 98%). This mixture was refluxed in an oil bath (ca. 423-433 K) for 5 h after which it was left to stand for 24 h. During this time a yellow precipitate formed. It was filtered and washed with distilled water, giving yellow crystals of the title compound (yield: 0.144 g, 0.45 mmol, 90%; m.p. 567–568 K). Yellow block-like crystals suitable for X-ray analysis were grown from a solution of ethanol:water (2:1) by slow evaporation at room temperature. The title product is insoluble in benzene, chloroform, acetic acid, acetone, DMF, and DMSO, but soluble in trifluoroacetic acid. ¹H NMR (400MHz, CDCl₃, δ, p.p.m., J/Hz): 3.15 (2H, td, J = 6.5; 2.9, β-CH₂), 4.16 (2H, t, J = 6.5, γ-CH₂), 7.44 (2H, d, J = 8.8, H-2′,6′), 7.60 (1H, dd, J = 7.9; 5.9, H-6), 7.83 (1H, t, J = 2.9, =CH), 7.98 (2H, d, J = 8.8, H-3′,5′), 8.63 (1H, dd, J = 5.9; 1.7, H-5), 9.00 (1H, dd, J = 7.9; 1.7, H-7). R_f = 0.47 (chloroform:methanol, 10:1).

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms were placed in calculated positions and included in the final cycles of refinement using a riding-model approximation: C—H = 0.93–0.97 Å with U_iso(H) = 1.2U_eq(C).

Table 2
Experimental details

Crystal data
Chemical formula	C₁₇H₁₂N₄O₃
M_r	320.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.1755 (3), 11.5855 (3), 17.2515 (5)
β (°)	90.360 (3)
V (Å³)	1434.12 (8)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	0.88
Crystal size (mm)	0.20 × 0.18 × 0.15

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ )
T_min, T_max	0.928, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10375, 2965, 2194
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.629

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.175, 1.08
No. of reflections	2965
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.20
Computer programs: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ), SHELXS97, XP and SHELXTL (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ) and Mercury (Macrae et al., 2008 ).

Supporting information

CCDC reference: 1456732

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989016003583/su5283sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989016003583/su5283Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989016003583/su5283Isup3.cml

checkCIF report

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: SHELXL2014 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(E)-9-(4-Nitrobenzylidene)-8,9-dihydropyrido[2,3-d]pyrrolo[1,2-a]pyrimidin-5(7H)-one top

Crystal data top

C₁₇H₁₂N₄O₃	F(000) = 664
M_r = 320.31	D_x = 1.483 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 7.1755 (3) Å	Cell parameters from 2842 reflections
b = 11.5855 (3) Å	θ = 4.6–75.6°
c = 17.2515 (5) Å	µ = 0.88 mm⁻¹
β = 90.360 (3)°	T = 293 K
V = 1434.12 (8) Å³	Block, yellow
Z = 4	0.20 × 0.18 × 0.15 mm

Data collection top

Oxford Diffraction Xcalibur Ruby diffractometer	2194 reflections with I > 2σ(I)
Detector resolution: 10.2576 pixels mm^-1	R_int = 0.045
ω scans	θ_max = 76.0°, θ_min = 4.6°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −8→9
T_min = 0.928, T_max = 1.000	k = −7→14
10375 measured reflections	l = −21→20
2965 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.057	H-atom parameters constrained
wR(F²) = 0.175	w = 1/[σ²(F_o²) + (0.0826P)² + 0.3825P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
2965 reflections	Δρ_max = 0.31 e Å⁻³
217 parameters	Δρ_min = −0.20 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
O1	0.7005 (3)	−0.09081 (15)	0.54727 (12)	0.0677 (6)
O2	0.9284 (3)	0.88109 (16)	0.33072 (13)	0.0718 (6)
O3	0.9755 (5)	0.7632 (2)	0.23673 (14)	0.0913 (9)
N1	0.6413 (3)	0.24377 (15)	0.62105 (12)	0.0462 (5)
N2	0.7312 (3)	0.10238 (16)	0.52922 (11)	0.0446 (5)
N3	0.5181 (4)	0.18637 (18)	0.73866 (13)	0.0584 (6)
N4	0.9345 (3)	0.78291 (19)	0.30362 (13)	0.0560 (6)
C1	0.7062 (3)	0.21345 (18)	0.55449 (13)	0.0428 (5)
C2	0.6831 (4)	0.00730 (19)	0.57260 (15)	0.0471 (5)
C3	0.5521 (4)	−0.0476 (2)	0.70117 (16)	0.0527 (6)
H3	0.5655	−0.1253	0.6891	0.063*
C4	0.4772 (4)	−0.0150 (2)	0.76967 (16)	0.0572 (7)
H4	0.4362	−0.0698	0.8051	0.069*
C5	0.4631 (5)	0.1021 (2)	0.78581 (16)	0.0611 (7)
H5	0.4114	0.1232	0.8330	0.073*
C6	0.5898 (3)	0.15420 (19)	0.66978 (14)	0.0454 (5)
C7	0.6088 (3)	0.03714 (19)	0.64897 (13)	0.0441 (5)
C8	0.7641 (3)	0.29244 (19)	0.49255 (13)	0.0428 (5)
C9	0.8364 (4)	0.2207 (2)	0.42615 (14)	0.0506 (6)
H9A	0.9678	0.2356	0.4178	0.061*
H9B	0.7685	0.2379	0.3787	0.061*
C10	0.8050 (4)	0.0949 (2)	0.45079 (15)	0.0526 (6)
H10A	0.7167	0.0572	0.4164	0.063*
H10B	0.9213	0.0522	0.4503	0.063*
C11	0.7470 (3)	0.4070 (2)	0.50057 (14)	0.0452 (5)
H11	0.6939	0.4308	0.5469	0.054*
C12	0.7990 (3)	0.50060 (19)	0.44770 (13)	0.0422 (5)
C13	0.8910 (4)	0.4833 (2)	0.37725 (15)	0.0502 (6)
H13	0.9231	0.4089	0.3621	0.060*
C14	0.9345 (4)	0.5759 (2)	0.33012 (14)	0.0495 (6)
H14	0.9938	0.5643	0.2830	0.059*
C15	0.8886 (3)	0.6858 (2)	0.35404 (13)	0.0459 (5)
C16	0.8010 (4)	0.7066 (2)	0.42325 (14)	0.0474 (5)
H16	0.7732	0.7816	0.4385	0.057*
C17	0.7552 (3)	0.6140 (2)	0.46970 (14)	0.0465 (5)
H17	0.6944	0.6270	0.5163	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1034 (16)	0.0362 (9)	0.0640 (12)	−0.0012 (9)	0.0249 (11)	−0.0063 (8)
O2	0.1033 (17)	0.0415 (10)	0.0708 (13)	−0.0056 (10)	0.0169 (12)	0.0069 (9)
O3	0.151 (2)	0.0669 (14)	0.0568 (13)	0.0001 (14)	0.0446 (15)	0.0151 (10)
N1	0.0638 (12)	0.0332 (9)	0.0419 (10)	−0.0014 (8)	0.0163 (9)	−0.0002 (7)
N2	0.0558 (11)	0.0365 (9)	0.0416 (10)	0.0003 (8)	0.0106 (8)	−0.0027 (7)
N3	0.0854 (16)	0.0414 (11)	0.0485 (12)	0.0009 (10)	0.0222 (11)	0.0014 (9)
N4	0.0722 (14)	0.0476 (11)	0.0485 (12)	−0.0036 (10)	0.0120 (10)	0.0120 (9)
C1	0.0499 (12)	0.0336 (10)	0.0448 (12)	0.0002 (8)	0.0075 (9)	−0.0014 (8)
C2	0.0582 (13)	0.0356 (11)	0.0476 (13)	−0.0007 (9)	0.0096 (10)	−0.0010 (9)
C3	0.0683 (15)	0.0383 (11)	0.0516 (14)	−0.0024 (11)	0.0052 (12)	0.0048 (10)
C4	0.0755 (17)	0.0467 (13)	0.0496 (14)	−0.0040 (12)	0.0113 (12)	0.0123 (11)
C5	0.087 (2)	0.0504 (14)	0.0460 (14)	0.0001 (13)	0.0224 (13)	0.0072 (11)
C6	0.0562 (13)	0.0387 (11)	0.0414 (11)	0.0005 (9)	0.0095 (10)	0.0026 (9)
C7	0.0517 (12)	0.0374 (11)	0.0433 (12)	−0.0003 (9)	0.0073 (10)	0.0014 (9)
C8	0.0496 (12)	0.0422 (12)	0.0368 (11)	−0.0013 (9)	0.0102 (9)	−0.0022 (9)
C9	0.0649 (14)	0.0481 (12)	0.0389 (12)	−0.0027 (11)	0.0120 (10)	−0.0025 (10)
C10	0.0688 (16)	0.0437 (12)	0.0455 (13)	−0.0001 (11)	0.0116 (12)	−0.0053 (10)
C11	0.0559 (13)	0.0409 (11)	0.0390 (11)	0.0001 (9)	0.0124 (9)	0.0010 (9)
C12	0.0498 (12)	0.0401 (11)	0.0369 (11)	−0.0017 (9)	0.0083 (9)	0.0012 (8)
C13	0.0695 (15)	0.0378 (11)	0.0435 (13)	0.0005 (10)	0.0154 (11)	−0.0026 (9)
C14	0.0687 (15)	0.0463 (12)	0.0335 (11)	−0.0020 (11)	0.0165 (10)	−0.0013 (9)
C15	0.0558 (13)	0.0405 (11)	0.0415 (12)	−0.0039 (9)	0.0040 (10)	0.0074 (9)
C16	0.0604 (14)	0.0377 (11)	0.0440 (12)	0.0016 (9)	0.0095 (10)	−0.0019 (9)
C17	0.0552 (13)	0.0438 (12)	0.0406 (12)	0.0019 (10)	0.0115 (10)	−0.0006 (9)

Geometric parameters (Å, º) top

O1—C2	1.225 (3)	C8—C11	1.340 (3)
O2—N4	1.231 (3)	C8—C9	1.510 (3)
O3—N4	1.214 (3)	C9—C10	1.535 (3)
N1—C1	1.291 (3)	C9—H9A	0.9700
N1—C6	1.387 (3)	C9—H9B	0.9700
N2—C1	1.371 (3)	C10—H10A	0.9700
N2—C2	1.377 (3)	C10—H10B	0.9700
N2—C10	1.459 (3)	C11—C12	1.467 (3)
N3—C5	1.332 (3)	C11—H11	0.9300
N3—C6	1.350 (3)	C12—C13	1.401 (3)
N4—C15	1.461 (3)	C12—C17	1.404 (3)
C1—C8	1.469 (3)	C13—C14	1.383 (3)
C2—C7	1.466 (3)	C13—H13	0.9300
C3—C4	1.355 (4)	C14—C15	1.379 (3)
C3—C7	1.394 (3)	C14—H14	0.9300
C3—H3	0.9300	C15—C16	1.374 (3)
C4—C5	1.389 (4)	C16—C17	1.380 (3)
C4—H4	0.9300	C16—H16	0.9300
C5—H5	0.9300	C17—H17	0.9300
C6—C7	1.410 (3)

C1—N1—C6	115.76 (19)	C8—C9—H9A	110.7
C1—N2—C2	123.0 (2)	C10—C9—H9A	110.7
C1—N2—C10	113.55 (19)	C8—C9—H9B	110.7
C2—N2—C10	123.40 (19)	C10—C9—H9B	110.7
C5—N3—C6	116.8 (2)	H9A—C9—H9B	108.8
O3—N4—O2	123.0 (2)	N2—C10—C9	104.79 (18)
O3—N4—C15	118.5 (2)	N2—C10—H10A	110.8
O2—N4—C15	118.5 (2)	C9—C10—H10A	110.8
N1—C1—N2	125.9 (2)	N2—C10—H10B	110.8
N1—C1—C8	125.7 (2)	C9—C10—H10B	110.8
N2—C1—C8	108.39 (19)	H10A—C10—H10B	108.9
O1—C2—N2	121.5 (2)	C8—C11—C12	130.1 (2)
O1—C2—C7	125.3 (2)	C8—C11—H11	114.9
N2—C2—C7	113.18 (19)	C12—C11—H11	114.9
C4—C3—C7	119.1 (2)	C13—C12—C17	118.4 (2)
C4—C3—H3	120.4	C13—C12—C11	123.8 (2)
C7—C3—H3	120.4	C17—C12—C11	117.8 (2)
C3—C4—C5	118.5 (2)	C14—C13—C12	120.5 (2)
C3—C4—H4	120.8	C14—C13—H13	119.7
C5—C4—H4	120.8	C12—C13—H13	119.7
N3—C5—C4	124.8 (3)	C15—C14—C13	119.0 (2)
N3—C5—H5	117.6	C15—C14—H14	120.5
C4—C5—H5	117.6	C13—C14—H14	120.5
N3—C6—N1	115.5 (2)	C16—C15—C14	122.3 (2)
N3—C6—C7	121.8 (2)	C16—C15—N4	119.2 (2)
N1—C6—C7	122.6 (2)	C14—C15—N4	118.5 (2)
C3—C7—C6	118.9 (2)	C15—C16—C17	118.7 (2)
C3—C7—C2	121.6 (2)	C15—C16—H16	120.7
C6—C7—C2	119.5 (2)	C17—C16—H16	120.7
C11—C8—C1	121.0 (2)	C16—C17—C12	121.1 (2)
C11—C8—C9	131.0 (2)	C16—C17—H17	119.5
C1—C8—C9	108.02 (19)	C12—C17—H17	119.5
C8—C9—C10	105.11 (19)

C6—N1—C1—N2	−1.3 (4)	N1—C1—C8—C11	−2.2 (4)
C6—N1—C1—C8	178.0 (2)	N2—C1—C8—C11	177.2 (2)
C2—N2—C1—N1	2.0 (4)	N1—C1—C8—C9	178.3 (2)
C10—N2—C1—N1	179.3 (2)	N2—C1—C8—C9	−2.4 (3)
C2—N2—C1—C8	−177.4 (2)	C11—C8—C9—C10	−175.8 (3)
C10—N2—C1—C8	−0.1 (3)	C1—C8—C9—C10	3.7 (3)
C1—N2—C2—O1	177.2 (3)	C1—N2—C10—C9	2.5 (3)
C10—N2—C2—O1	0.2 (4)	C2—N2—C10—C9	179.7 (2)
C1—N2—C2—C7	−1.9 (4)	C8—C9—C10—N2	−3.7 (3)
C10—N2—C2—C7	−178.9 (2)	C1—C8—C11—C12	178.5 (2)
C7—C3—C4—C5	−1.2 (5)	C9—C8—C11—C12	−2.1 (5)
C6—N3—C5—C4	1.1 (5)	C8—C11—C12—C13	−4.0 (4)
C3—C4—C5—N3	0.0 (5)	C8—C11—C12—C17	176.6 (3)
C5—N3—C6—N1	178.4 (3)	C17—C12—C13—C14	−1.1 (4)
C5—N3—C6—C7	−1.0 (4)	C11—C12—C13—C14	179.6 (3)
C1—N1—C6—N3	−178.6 (2)	C12—C13—C14—C15	1.0 (4)
C1—N1—C6—C7	0.8 (4)	C13—C14—C15—C16	0.0 (4)
C4—C3—C7—C6	1.2 (4)	C13—C14—C15—N4	−179.7 (2)
C4—C3—C7—C2	−177.2 (3)	O3—N4—C15—C16	−165.0 (3)
N3—C6—C7—C3	−0.1 (4)	O2—N4—C15—C16	14.5 (4)
N1—C6—C7—C3	−179.4 (2)	O3—N4—C15—C14	14.8 (4)
N3—C6—C7—C2	178.4 (2)	O2—N4—C15—C14	−165.7 (3)
N1—C6—C7—C2	−1.0 (4)	C14—C15—C16—C17	−1.0 (4)
O1—C2—C7—C3	0.8 (4)	N4—C15—C16—C17	178.8 (2)
N2—C2—C7—C3	179.9 (2)	C15—C16—C17—C12	0.9 (4)
O1—C2—C7—C6	−177.7 (3)	C13—C12—C17—C16	0.1 (4)
N2—C2—C7—C6	1.4 (3)	C11—C12—C17—C16	179.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N3ⁱ	0.93	2.58	3.292 (3)	133
C4—H4···N1ⁱ	0.93	2.57	3.480 (3)	166
C13—H13···O3ⁱⁱ	0.93	2.51	3.363 (3)	153
C16—H16···O1ⁱⁱⁱ	0.93	2.45	3.259 (3)	145

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+2, y−1/2, −z+1/2; (iii) x, y+1, z.

Acknowledgements

This work was supported by a Fundamental grant (FA-F7-T207: Theoretical aspects of formation of asymmetrical centers in biologically active heterocyclic molecules) from the Academy of Sciences of the Republic of Uzbekistan.

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