1-Benzyl-6-phenyl­imino-5-(pyrrol-2-yl­idene)hexa­hydro­pyrimidine-2,4-dione

Tamazyan, R.; Ayvazyan, A.; Martirosyan, V.; Avagyan, K.; Martirosyan, A.

doi:10.1107/S1600536808001384

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o483

doi:10.1107/S1600536808001384

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1-Benzyl-6-phenylimino-5-(pyrrol-2-ylidene)hexahydropyrimidine-2,4-dione

Rafael Tamazyan,^a ^* Armen Ayvazyan,^a Vahan Martirosyan,^b Kristine Avagyan ^b and Ashot Martirosyan ^b

^aMolecule Structure Research Center, National Academy of Sciences RA, Azatutyan Avenue 26, 375014 Yerevan, Republic of Armenia, and ^bInstitute of Fine Organic Chemistry, National Academy of Sciences RA, Azatutyan Avenue 26, 375014 Yerevan, Republic of Armenia
^*Correspondence e-mail: rafael@msrc.am

(Received 12 December 2007; accepted 14 January 2008; online 23 January 2008)

In the title compound, C₂₁H₂₀N₄O₂, a potential anti-human immunodeficiency virus type 1 (HIV-1) non-nucleoside reverse transcriptase inhibitor, the pyrrolidine ring adopts an envelope conformation, while the hydrogenated pyrimidine ring adopts a weakly expressed twist conformation. The molecules are connected into infinite chains via N—H⋯O hydrogen bonds.

Related literature

For related structures, see: Karapetyan et al. (2002 ); Tamazyan et al. (2002 ). For details of the pharmacological properties of similar compounds, see: De Clercq (1996 ).

Experimental

Crystal data

C₂₁H₂₀N₄O₂
M_r = 360.41
Triclinic, $[P \overline 1]$
a = 5.7844 (12) Å
b = 10.378 (2) Å
c = 15.595 (3) Å
α = 102.64 (3)°
β = 93.32 (3)°
γ = 102.45 (3)°
V = 886.6 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 (2) K
0.3 × 0.27 × 0.25 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
5619 measured reflections
5144 independent reflections
2944 reflections with I > 2σ(I)
R_int = 0.028
3 standard reflections frequency: 180 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.128
S = 1.04
5144 reflections
325 parameters
All H-atom parameters refined
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N10—H10⋯O7	0.90 (2)	2.03 (2)	2.664 (3)	127 (2)
N10—H10⋯O7ⁱ	0.90 (2)	2.22 (2)	2.891 (3)	131 (2)
N3—H3⋯O8ⁱⁱ	0.86 (2)	2.10 (2)	2.937 (3)	165 (2)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y, -z+1.

Data collection: CAD-4 Software (Enraf–Nonius 1988 ); cell refinement: CAD-4 Software; data reduction: HELENA (Spek, 1997 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and ORTEPII (Johnson, 1976 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808001384/pv2060sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808001384/pv2060Isup2.hkl

checkCIF report

Comment top

The interest to X-ray structural investigation of the title compound, (I), was stimulated by its potentially HIV-1 RT inhibition properties. It belong to the family of non-nucleoside reverse transcriptase inhibitors (NNRTIs).

A view of (I) with our numbering scheme is depicted in Fig. 1. A l l intramolecular interatomic distances in (I) are in good agreement with their mean statistical values. The crystal structure consists of infinite chains along [112] direction of crystal lattice. These chains are formed by molecules of (I) via O7···H10—N10 and O8···H3—N3 hydrogen bonds (Fig. 2).

Related literature top

For related structures, see: Karapetyan et al. (2002); Tamazyan et al. (2002). For details of the pharmacological properties of similar compounds, see: De Clercq (1996).

Experimental top

The title compound was synthesized by the condensation of 6-anilino-1-benzyl-1,2,3,4-tetrahydro-2,4-pyrimidinedione with pyrrolidon-2. The crystals were grown from an ethanol solution. A suitable crystal of the size ~0.3 mm was selected for X-ray diffraction experiment.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius 1988); cell refinement: CAD-4 Software (Enraf–Nonius 1988); data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of (I) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Unit cell packing of (I) showing infinite chains of molecules via hydrogen bonding; for clarifity only H atoms participating in bonding have been included. Symmetry cods: (i) 1 - x, 1 - y, 1 - z; (ii) 1 + x, 1 + y, z; (iii) -x, -y, 1 - z.

1-Benzyl-6-phenylimino-5-(pyrrol-2-ylidene)hexahydropyrimidine-2,4-dione top

Crystal data top

C₂₁H₂₀N₄O₂	Z = 2
M_r = 360.41	F(000) = 380
Triclinic, P1	D_x = 1.350 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.7844 (12) Å	Cell parameters from 22 reflections
b = 10.378 (2) Å	θ = 13–16°
c = 15.595 (3) Å	µ = 0.09 mm⁻¹
α = 102.64 (3)°	T = 293 K
β = 93.32 (3)°	Prism, colourless
γ = 102.45 (3)°	0.3 × 0.27 × 0.25 mm
V = 886.6 (3) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.028
Radiation source: fine-focus sealed tube	θ_max = 30.0°, θ_min = 1.4°
Graphite monochromator	h = 0→8
θ/2θ scans	k = −14→14
5619 measured reflections	l = −21→21
5144 independent reflections	3 standard reflections every 180 min
2944 reflections with I > 2σ(I)	intensity decay: none

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.065	All H-atom parameters refined
wR(F²) = 0.128	w = 1/[σ²(F_o²) + (0.0198P)² + 0.561P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
5144 reflections	Δρ_max = 0.27 e Å⁻³
325 parameters	Δρ_min = −0.26 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: 0.0124 (13)

Crystal data top

C₂₁H₂₀N₄O₂	γ = 102.45 (3)°
M_r = 360.41	V = 886.6 (3) Å³
Triclinic, P1	Z = 2
a = 5.7844 (12) Å	Mo Kα radiation
b = 10.378 (2) Å	µ = 0.09 mm⁻¹
c = 15.595 (3) Å	T = 293 K
α = 102.64 (3)°	0.3 × 0.27 × 0.25 mm
β = 93.32 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.028
5619 measured reflections	3 standard reflections every 180 min
5144 independent reflections	intensity decay: none
2944 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.128	All H-atom parameters refined
S = 1.04	Δρ_max = 0.27 e Å⁻³
5144 reflections	Δρ_min = −0.26 e Å⁻³
325 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
N1	0.4204 (3)	−0.03850 (16)	0.35608 (11)	0.0320 (4)
C2	0.2737 (4)	−0.0209 (2)	0.42132 (14)	0.0329 (5)
H3	0.163 (4)	0.120 (2)	0.4942 (16)	0.043 (7)*
N3	0.2672 (4)	0.11039 (18)	0.45813 (13)	0.0374 (5)
C4	0.4114 (4)	0.2259 (2)	0.44199 (13)	0.0312 (5)
C5	0.5484 (4)	0.20422 (19)	0.36835 (13)	0.0291 (4)
C6	0.5188 (4)	0.0671 (2)	0.31427 (14)	0.0295 (4)
O7	0.4116 (3)	0.33653 (15)	0.49159 (10)	0.0430 (4)
O8	0.1540 (3)	−0.11624 (15)	0.44595 (11)	0.0469 (4)
C9	0.7255 (4)	0.3145 (2)	0.35785 (13)	0.0300 (4)
H10	0.638 (4)	0.464 (2)	0.4363 (16)	0.044 (7)*
N10	0.7427 (4)	0.44206 (18)	0.39838 (13)	0.0393 (5)
C11	0.9511 (5)	0.5384 (2)	0.3816 (2)	0.0465 (6)
H11A	1.017 (5)	0.610 (3)	0.438 (2)	0.075 (9)*
H11B	0.906 (5)	0.585 (3)	0.3357 (18)	0.060 (8)*
C12	1.1099 (5)	0.4461 (3)	0.34836 (19)	0.0462 (6)
H12A	1.208 (5)	0.435 (3)	0.4041 (19)	0.066 (9)*
H12B	1.215 (5)	0.476 (3)	0.3058 (17)	0.058 (8)*
C13	0.9361 (4)	0.3101 (3)	0.30583 (17)	0.0401 (6)
H13A	0.993 (5)	0.228 (3)	0.3025 (17)	0.054 (8)*
H13B	0.890 (5)	0.310 (3)	0.245 (2)	0.071 (9)*
N14	0.5687 (3)	0.02327 (18)	0.23576 (12)	0.0367 (4)
C15	0.5951 (4)	0.0974 (2)	0.16998 (14)	0.0342 (5)
C16	0.4413 (5)	0.1784 (3)	0.15504 (17)	0.0457 (6)
H16	0.325 (4)	0.192 (2)	0.1957 (16)	0.048 (7)*
C17	0.4605 (6)	0.2394 (3)	0.08445 (19)	0.0578 (8)
H17	0.351 (5)	0.292 (3)	0.0734 (19)	0.069 (9)*
C18	0.6315 (6)	0.2211 (3)	0.02769 (18)	0.0593 (8)
H18	0.646 (5)	0.263 (3)	−0.024 (2)	0.072 (9)*
C19	0.7829 (5)	0.1407 (3)	0.04185 (17)	0.0533 (7)
H19	0.904 (5)	0.127 (3)	0.002 (2)	0.072 (9)*
C20	0.7642 (5)	0.0783 (3)	0.11150 (16)	0.0439 (6)
H20	0.866 (5)	0.023 (3)	0.1218 (17)	0.056 (8)*
C21	0.4193 (4)	−0.1793 (2)	0.31229 (15)	0.0350 (5)
H21A	0.575 (4)	−0.179 (2)	0.2917 (14)	0.033 (6)*
H21B	0.403 (4)	−0.229 (2)	0.3603 (15)	0.037 (6)*
C22	0.2243 (4)	−0.2461 (2)	0.23746 (14)	0.0334 (5)
C23	0.2296 (5)	−0.3733 (2)	0.18596 (16)	0.0417 (6)
H23	0.367 (5)	−0.412 (3)	0.1979 (17)	0.058 (8)*
C24	0.0439 (5)	−0.4443 (3)	0.12153 (18)	0.0528 (7)
H24	0.049 (5)	−0.533 (3)	0.0869 (17)	0.059 (8)*
C25	−0.1440 (5)	−0.3884 (3)	0.10493 (18)	0.0546 (7)
H25	−0.276 (5)	−0.439 (3)	0.0577 (18)	0.064 (8)*
C26	−0.1472 (5)	−0.2606 (3)	0.15307 (17)	0.0482 (6)
H26	−0.285 (5)	−0.219 (3)	0.1429 (17)	0.061 (8)*
C27	0.0355 (5)	−0.1909 (2)	0.21906 (16)	0.0415 (6)
H27	0.030 (4)	−0.103 (2)	0.2539 (15)	0.038 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0374 (10)	0.0241 (8)	0.0323 (9)	0.0033 (7)	0.0113 (8)	0.0042 (7)
C2	0.0368 (12)	0.0286 (10)	0.0328 (11)	0.0050 (9)	0.0096 (9)	0.0071 (9)
N3	0.0432 (11)	0.0282 (9)	0.0404 (11)	0.0049 (8)	0.0219 (9)	0.0063 (8)
C4	0.0339 (12)	0.0288 (10)	0.0307 (11)	0.0062 (9)	0.0062 (9)	0.0066 (9)
C5	0.0318 (11)	0.0260 (10)	0.0284 (10)	0.0030 (8)	0.0086 (9)	0.0062 (8)
C6	0.0288 (11)	0.0259 (10)	0.0330 (11)	0.0030 (8)	0.0090 (9)	0.0072 (8)
O7	0.0566 (11)	0.0281 (8)	0.0424 (9)	0.0071 (7)	0.0204 (8)	0.0032 (7)
O8	0.0581 (11)	0.0319 (8)	0.0532 (10)	0.0052 (8)	0.0276 (9)	0.0153 (7)
C9	0.0301 (11)	0.0318 (11)	0.0268 (10)	0.0046 (9)	0.0026 (8)	0.0069 (8)
N10	0.0418 (12)	0.0279 (9)	0.0462 (12)	0.0024 (8)	0.0149 (10)	0.0079 (8)
C11	0.0464 (15)	0.0323 (12)	0.0540 (16)	−0.0060 (11)	0.0077 (13)	0.0106 (12)
C12	0.0374 (14)	0.0424 (14)	0.0541 (16)	−0.0033 (11)	0.0071 (12)	0.0136 (12)
C13	0.0340 (13)	0.0371 (13)	0.0453 (14)	0.0011 (10)	0.0120 (11)	0.0067 (11)
N14	0.0441 (11)	0.0309 (9)	0.0336 (10)	0.0047 (8)	0.0141 (8)	0.0063 (8)
C15	0.0361 (12)	0.0310 (11)	0.0289 (11)	−0.0022 (9)	0.0075 (9)	0.0022 (9)
C16	0.0410 (14)	0.0533 (15)	0.0411 (14)	0.0068 (12)	0.0079 (12)	0.0111 (11)
C17	0.0546 (18)	0.0641 (18)	0.0554 (17)	0.0070 (15)	−0.0062 (14)	0.0257 (15)
C18	0.066 (2)	0.0638 (18)	0.0395 (15)	−0.0107 (15)	−0.0006 (14)	0.0215 (13)
C19	0.0581 (18)	0.0554 (16)	0.0340 (13)	−0.0086 (14)	0.0138 (13)	0.0035 (12)
C20	0.0500 (15)	0.0402 (13)	0.0382 (13)	0.0056 (12)	0.0165 (12)	0.0045 (11)
C21	0.0407 (13)	0.0280 (11)	0.0371 (12)	0.0089 (10)	0.0116 (10)	0.0065 (9)
C22	0.0390 (12)	0.0267 (10)	0.0333 (11)	0.0026 (9)	0.0114 (10)	0.0081 (8)
C23	0.0543 (16)	0.0312 (12)	0.0383 (13)	0.0081 (11)	0.0136 (12)	0.0050 (10)
C24	0.0671 (19)	0.0366 (14)	0.0437 (14)	0.0029 (13)	0.0119 (14)	−0.0061 (11)
C25	0.0545 (18)	0.0550 (17)	0.0405 (14)	−0.0035 (14)	0.0009 (13)	−0.0001 (12)
C26	0.0418 (15)	0.0514 (15)	0.0472 (15)	0.0050 (12)	0.0026 (12)	0.0094 (12)
C27	0.0456 (14)	0.0316 (12)	0.0443 (13)	0.0068 (10)	0.0089 (11)	0.0040 (10)

Geometric parameters (Å, º) top

N1—C2	1.369 (3)	C15—C16	1.391 (3)
N1—C6	1.427 (2)	C15—C20	1.392 (3)
N1—C21	1.470 (3)	C16—C17	1.383 (4)
C2—O8	1.228 (2)	C16—H16	0.96 (3)
C2—N3	1.368 (3)	C17—C18	1.381 (4)
N3—C4	1.386 (3)	C17—H17	0.95 (3)
N3—H3	0.86 (2)	C18—C19	1.373 (4)
C4—O7	1.236 (2)	C18—H18	0.99 (3)
C4—C5	1.437 (3)	C19—C20	1.379 (4)
C5—C9	1.408 (3)	C19—H19	0.97 (3)
C5—C6	1.455 (3)	C20—H20	0.93 (3)
C6—N14	1.282 (3)	C21—C22	1.507 (3)
C9—N10	1.316 (3)	C21—H21A	0.97 (2)
C9—C13	1.506 (3)	C21—H21B	0.99 (2)
N10—C11	1.467 (3)	C22—C27	1.381 (3)
N10—H10	0.90 (2)	C22—C23	1.395 (3)
C11—C12	1.499 (4)	C23—C24	1.384 (4)
C11—H11A	1.01 (3)	C23—H23	0.99 (3)
C11—H11B	1.00 (3)	C24—C25	1.375 (4)
C12—C13	1.531 (3)	C24—H24	0.96 (3)
C12—H12A	1.05 (3)	C25—C26	1.379 (4)
C12—H12B	0.98 (3)	C25—H25	1.00 (3)
C13—H13A	0.97 (3)	C26—C27	1.384 (4)
C13—H13B	0.97 (3)	C26—H26	1.00 (3)
N14—C15	1.407 (3)	C27—H27	0.96 (2)

C2—N1—C6	122.57 (17)	C16—C15—C20	118.3 (2)
C2—N1—C21	116.70 (17)	C16—C15—N14	122.3 (2)
C6—N1—C21	118.51 (17)	C20—C15—N14	119.0 (2)
O8—C2—N3	121.31 (19)	C17—C16—C15	120.3 (3)
O8—C2—N1	122.72 (19)	C17—C16—H16	121.3 (15)
N3—C2—N1	115.97 (18)	C15—C16—H16	118.4 (15)
C2—N3—C4	126.16 (19)	C18—C17—C16	120.8 (3)
C2—N3—H3	115.4 (16)	C18—C17—H17	119.4 (18)
C4—N3—H3	118.5 (16)	C16—C17—H17	119.7 (18)
O7—C4—N3	117.81 (19)	C19—C18—C17	119.1 (3)
O7—C4—C5	126.25 (19)	C19—C18—H18	119.3 (17)
N3—C4—C5	115.94 (18)	C17—C18—H18	121.6 (17)
C9—C5—C4	118.04 (18)	C18—C19—C20	120.6 (3)
C9—C5—C6	122.50 (18)	C18—C19—H19	120.2 (18)
C4—C5—C6	119.06 (17)	C20—C19—H19	119.2 (18)
N14—C6—N1	113.57 (18)	C19—C20—C15	120.8 (3)
N14—C6—C5	131.61 (19)	C19—C20—H20	121.4 (16)
N1—C6—C5	114.81 (17)	C15—C20—H20	117.7 (16)
N10—C9—C5	124.5 (2)	N1—C21—C22	115.08 (19)
N10—C9—C13	107.55 (19)	N1—C21—H21A	107.5 (13)
C5—C9—C13	127.79 (19)	C22—C21—H21A	110.5 (13)
C9—N10—C11	114.7 (2)	N1—C21—H21B	104.6 (13)
C9—N10—H10	120.3 (16)	C22—C21—H21B	110.5 (13)
C11—N10—H10	124.8 (16)	H21A—C21—H21B	108.3 (18)
N10—C11—C12	101.68 (19)	C27—C22—C23	118.0 (2)
N10—C11—H11A	109.7 (17)	C27—C22—C21	123.7 (2)
C12—C11—H11A	115.6 (17)	C23—C22—C21	118.2 (2)
N10—C11—H11B	110.5 (16)	C24—C23—C22	120.5 (3)
C12—C11—H11B	111.4 (16)	C24—C23—H23	121.3 (16)
H11A—C11—H11B	108 (2)	C22—C23—H23	118.2 (16)
C11—C12—C13	103.9 (2)	C25—C24—C23	120.6 (3)
C11—C12—H12A	106.9 (15)	C25—C24—H24	119.8 (16)
C13—C12—H12A	108.7 (15)	C23—C24—H24	119.5 (16)
C11—C12—H12B	115.1 (15)	C24—C25—C26	119.6 (3)
C13—C12—H12B	110.6 (15)	C24—C25—H25	120.6 (16)
H12A—C12—H12B	111 (2)	C26—C25—H25	119.9 (16)
C9—C13—C12	103.0 (2)	C25—C26—C27	119.9 (3)
C9—C13—H13A	113.3 (15)	C25—C26—H26	120.6 (16)
C12—C13—H13A	117.7 (16)	C27—C26—H26	119.4 (16)
C9—C13—H13B	109.5 (18)	C22—C27—C26	121.4 (2)
C12—C13—H13B	107.9 (17)	C22—C27—H27	118.9 (14)
H13A—C13—H13B	105 (2)	C26—C27—H27	119.7 (14)
C6—N14—C15	125.54 (19)

C6—N1—C2—O8	166.1 (2)	N10—C9—C13—C12	18.0 (3)
C21—N1—C2—O8	3.3 (3)	C5—C9—C13—C12	−157.6 (2)
C6—N1—C2—N3	−13.8 (3)	C11—C12—C13—C9	−28.8 (3)
C21—N1—C2—N3	−176.6 (2)	N1—C6—N14—C15	158.8 (2)
O8—C2—N3—C4	173.1 (2)	C5—C6—N14—C15	−22.4 (4)
N1—C2—N3—C4	−7.0 (3)	C6—N14—C15—C16	−42.4 (3)
C2—N3—C4—O7	−167.7 (2)	C6—N14—C15—C20	144.7 (2)
C2—N3—C4—C5	12.0 (3)	C20—C15—C16—C17	−1.0 (4)
O7—C4—C5—C9	9.8 (3)	N14—C15—C16—C17	−174.0 (2)
N3—C4—C5—C9	−169.9 (2)	C15—C16—C17—C18	0.1 (4)
O7—C4—C5—C6	−177.4 (2)	C16—C17—C18—C19	0.3 (4)
N3—C4—C5—C6	3.0 (3)	C17—C18—C19—C20	0.3 (4)
C2—N1—C6—N14	−154.0 (2)	C18—C19—C20—C15	−1.3 (4)
C21—N1—C6—N14	8.5 (3)	C16—C15—C20—C19	1.6 (3)
C2—N1—C6—C5	27.1 (3)	N14—C15—C20—C19	174.8 (2)
C21—N1—C6—C5	−170.4 (2)	C2—N1—C21—C22	84.4 (2)
C9—C5—C6—N14	−26.9 (4)	C6—N1—C21—C22	−79.1 (2)
C4—C5—C6—N14	160.5 (2)	N1—C21—C22—C27	−10.3 (3)
C9—C5—C6—N1	151.8 (2)	N1—C21—C22—C23	172.27 (19)
C4—C5—C6—N1	−20.7 (3)	C27—C22—C23—C24	−3.3 (3)
C4—C5—C9—N10	−15.1 (3)	C21—C22—C23—C24	174.3 (2)
C6—C5—C9—N10	172.4 (2)	C22—C23—C24—C25	2.5 (4)
C4—C5—C9—C13	159.9 (2)	C23—C24—C25—C26	−0.1 (4)
C6—C5—C9—C13	−12.7 (4)	C24—C25—C26—C27	−1.6 (4)
C5—C9—N10—C11	176.1 (2)	C23—C22—C27—C26	1.6 (3)
C13—C9—N10—C11	0.3 (3)	C21—C22—C27—C26	−175.8 (2)
C9—N10—C11—C12	−18.9 (3)	C25—C26—C27—C22	0.8 (4)
N10—C11—C12—C13	28.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N10—H10···O7	0.90 (2)	2.03 (2)	2.664 (3)	127 (2)
N10—H10···O7ⁱ	0.90 (2)	2.22 (2)	2.891 (3)	131 (2)
N3—H3···O8ⁱⁱ	0.86 (2)	2.10 (2)	2.937 (3)	165 (2)

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₀N₄O₂
M_r	360.41
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	5.7844 (12), 10.378 (2), 15.595 (3)
α, β, γ (°)	102.64 (3), 93.32 (3), 102.45 (3)
V (Å³)	886.6 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.3 × 0.27 × 0.25

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5619, 5144, 2944
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.128, 1.04
No. of reflections	5144
No. of parameters	325
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.26

Computer programs: CAD-4 Software (Enraf–Nonius 1988), HELENA (Spek, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and ORTEPII (Johnson, 1976), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N10—H10···O7	0.90 (2)	2.03 (2)	2.664 (3)	127 (2)
N10—H10···O7ⁱ	0.90 (2)	2.22 (2)	2.891 (3)	131 (2)
N3—H3···O8ⁱⁱ	0.86 (2)	2.10 (2)	2.937 (3)	165 (2)

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

Acknowledgements

This research was carried out within the framework of the Armenian Science and Education Foundation (ANSEF, grant No. PS-chemorg-907). The authors express their thanks to ANSEF.

References

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