1-Methyl-4-phenyl-3-[4-(tri­fluoro­meth­yl)phen­yl]-1H-pyrazolo­[3,4-d]pyrimidine

El Hafi, M.; Boulhaoua, M.; Lahmidi, S.; Ramli, Y.; Essassi, E.M.; Mague, J.T.

doi:10.1107/S2414314618008751

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 6| June 2018| x180875

https://doi.org/10.1107/S2414314618008751

Open

access

1-Methyl-4-phenyl-3-[4-(trifluoromethyl)phenyl]-1H-pyrazolo[3,4-d]pyrimidine

Mohamed El Hafi,^a ^* Mohammed Boulhaoua,^a Sanae Lahmidi,^a Youssef Ramli,^b El Mokhtar Essassi ^a and Joel T. Mague ^c

^aLaboratoire de Chimie Organique Hétérocyclique, Centre de Recherche Des Sciences des Médicaments, Pôle de Compétence Pharmacochimie, Av Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco, ^bLaboratory of Medicinal Chemistry, Faculty of Medicine and Pharmacy, Mohammed V, University Rabat, Morocco, and ^cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
^*Correspondence e-mail: m.elhafi1@yahoo.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 8 June 2018; accepted 14 June 2018; online 26 June 2018)

In the title molecule, C₁₉H₁₃F₃N₄, the pyrazolopyrimidine unit is slightly non-planar [dihedral angle between the five- and six-membered rings = 3.03 (15)°]. In the crystal, offset head-to-tail π-stacking interactions between pyrazolopyrimidine units [centroid–centroid separation = 3.665 (2) Å] together with weak C—H⋯N hydrogen bonds form stepped chains propagating along the c-axis direction. The structure was refined as a two-component twin.

Keywords: crystal structure; hydrogen bond; π-stacking; pyrimidine; crystal structure.

CCDC reference: 1849367

Structure description

Pyrazolo [3,4-d] pyrimidine derivatives display a broad spectrum of biological properties, such as antiviral (Bektemirov et al., 1981 ), antibacterial (Rostamizadeh et al., 2013 ) and antitumor (Tintori et al., 2015 ). The present work is a continuation of our studies of pyrazolo[3,4-d]pyrimidine derivatives (El Hafi et al., 2017 ).

In the title molecule (Fig. 1), the pyrazolopyrimidine unit is slightly non-planar as indicated by the dihedral angle of 3.03 (15)° between the mean planes of the five- and six-membered rings. The plane of the C7–C12 benzene ring bearing the CF₃ substituent is inclined to the pyrazole moiety by 31.98 (16)° while the plane of the C14–C19 benzene ring is inclined by 50.69 (14)° to that of the pyrimidine ring.

Figure 1
The title molecule with 50% probability ellipsoids.

In the crystal, offset, head-to-tail π-stacking interactions between adjacent pyrazolopyrimidine units reinforced by weak, complementary C6—H6B⋯N1 hydrogen bonds form centrosymmetric dimers, which are connected into stepped chains along the c axis direction by weak, complementary C4—H4⋯N2 hydrogen bonds (Table 1 and Figs. 2 and 3). The centroid–centroid distance for the π-stacking interaction is 3.665 (2) Å.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯N2ⁱ	0.96 (3)	2.66 (3)	3.588 (4)	162 (2)
C6—H6B⋯N1ⁱⁱ	1.01 (4)	2.64 (3)	3.346 (4)	127 (2)
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+1, -y+1, -z+1.

Figure 2
Detail of the stepped chain formed by C—H⋯N hydrogen bonds (black dashed lines) and offset π-stacking interactions (orange dashed lines).

Figure 3
Packing projected along the c-axis direction giving end views of three adjacent chains. Intermolecular interactions are depicted as in Fig. 2

Synthesis and crystallization

A mixture 1-methyl-4-phenyl-1H-pyrazolo [3,4-d] pyrimidine (0.1 g, 0.47 mmol), 4-iodobenzotrifluoride (0.26 g, 0.95 mmol), Cs₂CO₃ (0.46 g, 1.42 mmol), K₃PO₄ (0.25 g, 1.18 mmol), 1,10- phenanthroline (0.034 g, 0.19 mmol), and Pd(OAc)₂ (0.021 g, 0.094 mmol) was dissolved/suspended in DMA (3 ml). The resulting mixture was flushed with argon and heated to 165°C for 48 h. After completion of the reaction, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Water (15 ml) was added, and the resulting aqueous phase was extracted with CH₂Cl₂ (3 × 15 ml). The combined organic layers were dried with MgSO₄ and concentrated under vacuum. The residue was purified by column chromatography on silica gel (mixed solvents of EtOAc/ petroleum ether). The title compound was recrystallized from ethanol solution at room temperature in the form of colourless plates (yield: 65%; m.p. 418–420 K).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The structure was refined as a two-component twin.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₉H₁₃F₃N₄
M_r	354.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	15.0553 (10), 15.7338 (12), 6.9701 (5)
β (°)	99.540 (4)
V (Å³)	1628.2 (2)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	0.96
Crystal size (mm)	0.19 × 0.12 × 0.02

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (TWINABS; Sheldrick, 2009 )
T_min, T_max	0.84, 0.98
No. of measured, independent and observed [I > 2σ(I)] reflections	17099, 16740, 12748
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.147, 1.03
No. of reflections	16740
No. of parameters	288
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.44
Computer programs: APEX3 and SAINT (Bruker, 2016 ), SHELXT (Sheldrick, 2015a ), SHELXL2016 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ), SHELXTL (Sheldrick, 2008a ) and CELL_NOW (Sheldrick, 2008b ).

Structural data

CCDC reference: 1849367

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314618008751/hb4239sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618008751/hb4239Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314618008751/hb4239Isup3.cdx

Supporting information file. DOI: https://doi.org/10.1107/S2414314618008751/hb4239Isup4.cml

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008a), CELL_NOW (Sheldrick, 2008b).

1-Methyl-4-phenyl-3-[4-(trifluoromethyl)phenyl]-1H-pyrazolo[3,4-d]pyrimidine top

Crystal data top

C₁₉H₁₃F₃N₄	F(000) = 728
M_r = 354.33	D_x = 1.445 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
a = 15.0553 (10) Å	Cell parameters from 9981 reflections
b = 15.7338 (12) Å	θ = 3.0–72.5°
c = 6.9701 (5) Å	µ = 0.96 mm⁻¹
β = 99.540 (4)°	T = 150 K
V = 1628.2 (2) Å³	Plate, colourless
Z = 4	0.19 × 0.12 × 0.02 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	16740 independent reflections
Radiation source: INCOATEC IµS micro-focus source	12748 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.046
Detector resolution: 10.4167 pixels mm^-1	θ_max = 72.5°, θ_min = 3.0°
ω scans	h = −18→18
Absorption correction: multi-scan (TWINABS; Sheldrick, 2009)	k = −18→18
T_min = 0.84, T_max = 0.98	l = −8→8
17099 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)] = 0.060	Hydrogen site location: difference Fourier map
wR(F²) = 0.147	All H-atom parameters refined
S = 1.02	w = 1/[σ²(F_o²) + (0.0509P)² + 0.8087P] where P = (F_o² + 2F_c²)/3
16740 reflections	(Δ/σ)_max < 0.001
288 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Special details top

Experimental. Analysis of 1332 reflections having I/σ(I) > 12 and chosen from the full data set with CELL_NOW (Sheldrick, 2008b) showed the crystal to belong to the monoclinic system and to be twinned by a 180° rotation about the a axis. The raw data were processed using the multi-component version ofSAINT under control of the two-component orientation file generated by CELL_NOW.

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.

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 > 2sigma(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. Refined as a 2-component twin.

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

	x	y	z	U_iso*/U_eq
F1	0.93746 (17)	0.43794 (15)	−0.1891 (4)	0.0744 (8)
F2	1.00377 (15)	0.3438 (2)	−0.0044 (4)	0.0895 (10)
F3	0.90729 (18)	0.31053 (18)	−0.2496 (4)	0.0824 (9)
N1	0.64088 (16)	0.55427 (16)	0.7611 (4)	0.0311 (6)
N2	0.52893 (16)	0.44411 (16)	0.7545 (4)	0.0315 (6)
N3	0.53400 (15)	0.34150 (15)	0.4998 (4)	0.0300 (6)
N4	0.58613 (15)	0.32541 (15)	0.3609 (4)	0.0305 (6)
C1	0.64887 (18)	0.38622 (18)	0.3746 (4)	0.0277 (6)
C2	0.63661 (18)	0.44456 (18)	0.5265 (4)	0.0266 (6)
C3	0.67118 (18)	0.52239 (18)	0.6055 (4)	0.0274 (6)
C4	0.5736 (2)	0.5126 (2)	0.8265 (5)	0.0337 (7)
H4	0.5549 (19)	0.5358 (19)	0.941 (5)	0.031 (8)*
C5	0.56320 (18)	0.41149 (18)	0.6036 (4)	0.0274 (6)
C6	0.4576 (2)	0.2875 (2)	0.5169 (6)	0.0353 (7)
H6A	0.477 (2)	0.228 (2)	0.522 (6)	0.048 (10)*
H6B	0.407 (2)	0.298 (2)	0.405 (6)	0.036 (9)*
H6C	0.435 (2)	0.305 (2)	0.635 (7)	0.053 (11)*
C7	0.71865 (19)	0.38123 (18)	0.2509 (4)	0.0272 (6)
C8	0.6999 (2)	0.34624 (19)	0.0652 (5)	0.0294 (7)
H8	0.641 (2)	0.3240 (17)	0.017 (5)	0.023 (7)*
C9	0.7662 (2)	0.33996 (19)	−0.0502 (5)	0.0311 (7)
H9	0.753 (2)	0.315 (2)	−0.175 (6)	0.048 (10)*
C10	0.8521 (2)	0.36943 (18)	0.0192 (5)	0.0306 (7)
C11	0.8724 (2)	0.4041 (2)	0.2034 (5)	0.0338 (7)
H11	0.935 (2)	0.425 (2)	0.253 (6)	0.045 (10)*
C12	0.8064 (2)	0.4091 (2)	0.3195 (5)	0.0322 (7)
H12	0.821 (2)	0.434 (2)	0.447 (5)	0.036 (9)*
C13	0.9243 (2)	0.3649 (2)	−0.1037 (5)	0.0370 (8)
C14	0.73663 (19)	0.57372 (18)	0.5194 (5)	0.0282 (7)
C15	0.8139 (2)	0.6051 (2)	0.6335 (5)	0.0333 (7)
H15	0.828 (2)	0.592 (2)	0.772 (6)	0.042 (10)*
C16	0.8760 (2)	0.6503 (2)	0.5480 (6)	0.0405 (8)
H16	0.931 (2)	0.668 (2)	0.627 (6)	0.044 (10)*
C17	0.8595 (2)	0.6674 (2)	0.3512 (6)	0.0427 (9)
H17	0.903 (3)	0.698 (2)	0.296 (6)	0.053 (11)*
C18	0.7813 (2)	0.6387 (2)	0.2375 (6)	0.0418 (8)
H18	0.768 (2)	0.652 (2)	0.110 (6)	0.052 (11)*
C19	0.7201 (2)	0.5910 (2)	0.3209 (5)	0.0341 (7)
H19	0.668 (2)	0.570 (2)	0.245 (6)	0.040 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0874 (17)	0.0592 (15)	0.092 (2)	0.0045 (12)	0.0588 (16)	0.0163 (13)
F2	0.0474 (13)	0.177 (3)	0.0493 (14)	0.0533 (16)	0.0231 (12)	0.0258 (17)
F3	0.0830 (17)	0.0977 (19)	0.0802 (19)	−0.0278 (14)	0.0537 (15)	−0.0485 (16)
N1	0.0312 (13)	0.0380 (14)	0.0253 (13)	0.0007 (10)	0.0077 (11)	−0.0008 (11)
N2	0.0297 (13)	0.0390 (15)	0.0268 (14)	0.0030 (10)	0.0075 (11)	0.0033 (11)
N3	0.0280 (12)	0.0331 (14)	0.0300 (14)	0.0000 (10)	0.0082 (11)	0.0020 (11)
N4	0.0287 (12)	0.0319 (14)	0.0322 (14)	0.0037 (10)	0.0092 (12)	0.0026 (11)
C1	0.0245 (14)	0.0318 (16)	0.0268 (15)	0.0046 (11)	0.0039 (12)	0.0009 (13)
C2	0.0235 (13)	0.0323 (16)	0.0239 (15)	0.0031 (11)	0.0039 (12)	0.0022 (12)
C3	0.0256 (14)	0.0339 (16)	0.0222 (15)	0.0036 (11)	0.0024 (12)	0.0016 (12)
C4	0.0343 (16)	0.0433 (19)	0.0252 (16)	0.0038 (13)	0.0100 (13)	0.0014 (13)
C5	0.0263 (14)	0.0322 (16)	0.0233 (15)	0.0041 (11)	0.0033 (12)	0.0033 (12)
C6	0.0327 (16)	0.0340 (18)	0.041 (2)	−0.0034 (13)	0.0116 (16)	0.0027 (14)
C7	0.0288 (14)	0.0261 (15)	0.0274 (16)	0.0045 (11)	0.0065 (13)	0.0034 (12)
C8	0.0300 (15)	0.0268 (15)	0.0308 (17)	0.0003 (12)	0.0030 (13)	0.0002 (13)
C9	0.0369 (16)	0.0306 (16)	0.0259 (16)	0.0040 (12)	0.0059 (14)	−0.0024 (13)
C10	0.0314 (15)	0.0287 (15)	0.0336 (17)	0.0063 (12)	0.0108 (13)	0.0017 (13)
C11	0.0268 (15)	0.0361 (17)	0.0388 (18)	0.0023 (12)	0.0063 (14)	−0.0069 (14)
C12	0.0279 (15)	0.0385 (18)	0.0297 (18)	0.0054 (12)	0.0034 (13)	−0.0074 (13)
C13	0.0396 (17)	0.0376 (18)	0.0360 (19)	0.0053 (13)	0.0125 (15)	−0.0004 (14)
C14	0.0272 (14)	0.0285 (16)	0.0303 (17)	0.0028 (11)	0.0089 (13)	−0.0023 (13)
C15	0.0316 (16)	0.0360 (17)	0.0324 (18)	0.0016 (12)	0.0060 (14)	−0.0053 (14)
C16	0.0328 (17)	0.0355 (18)	0.054 (2)	−0.0033 (13)	0.0105 (17)	−0.0080 (17)
C17	0.0418 (19)	0.0365 (19)	0.055 (2)	−0.0040 (15)	0.0250 (18)	−0.0006 (17)
C18	0.049 (2)	0.043 (2)	0.038 (2)	0.0016 (15)	0.0202 (17)	0.0044 (15)
C19	0.0342 (17)	0.0399 (18)	0.0287 (18)	−0.0001 (14)	0.0070 (14)	0.0000 (14)

Geometric parameters (Å, º) top

F1—C13	1.324 (4)	C7—C12	1.399 (4)
F2—C13	1.321 (4)	C8—C9	1.385 (4)
F3—C13	1.321 (4)	C8—H8	0.96 (3)
N1—C3	1.342 (4)	C9—C10	1.383 (4)
N1—C4	1.348 (4)	C9—H9	0.95 (4)
N2—C4	1.324 (4)	C10—C11	1.382 (5)
N2—C5	1.347 (4)	C10—C13	1.493 (4)
N3—C5	1.350 (4)	C11—C12	1.384 (4)
N3—N4	1.367 (3)	C11—H11	1.00 (4)
N3—C6	1.451 (4)	C12—H12	0.97 (4)
N4—C1	1.337 (4)	C14—C15	1.387 (4)
C1—C2	1.436 (4)	C14—C19	1.392 (5)
C1—C7	1.468 (4)	C15—C16	1.386 (5)
C2—C3	1.406 (4)	C15—H15	0.98 (4)
C2—C5	1.406 (4)	C16—C17	1.379 (6)
C3—C14	1.476 (4)	C16—H16	0.96 (4)
C4—H4	0.96 (3)	C17—C18	1.382 (5)
C6—H6A	0.99 (4)	C17—H17	0.94 (4)
C6—H6B	1.01 (4)	C18—C19	1.387 (5)
C6—H6C	0.98 (5)	C18—H18	0.90 (4)
C7—C8	1.392 (4)	C19—H19	0.94 (4)

C3—N1—C4	117.8 (3)	C8—C9—H9	121 (2)
C4—N2—C5	111.7 (3)	C11—C10—C9	120.5 (3)
C5—N3—N4	110.9 (2)	C11—C10—C13	118.8 (3)
C5—N3—C6	128.7 (3)	C9—C10—C13	120.7 (3)
N4—N3—C6	120.4 (3)	C10—C11—C12	119.7 (3)
C1—N4—N3	107.4 (2)	C10—C11—H11	120 (2)
N4—C1—C2	109.6 (2)	C12—C11—H11	120 (2)
N4—C1—C7	119.1 (3)	C11—C12—C7	120.8 (3)
C2—C1—C7	131.3 (3)	C11—C12—H12	119.0 (19)
C3—C2—C5	115.8 (3)	C7—C12—H12	120.2 (19)
C3—C2—C1	139.5 (3)	F3—C13—F2	106.5 (3)
C5—C2—C1	104.5 (2)	F3—C13—F1	103.9 (3)
N1—C3—C2	119.2 (3)	F2—C13—F1	105.3 (3)
N1—C3—C14	117.6 (3)	F3—C13—C10	114.0 (3)
C2—C3—C14	123.1 (3)	F2—C13—C10	113.2 (3)
N2—C4—N1	129.1 (3)	F1—C13—C10	113.2 (3)
N2—C4—H4	115.1 (18)	C15—C14—C19	119.7 (3)
N1—C4—H4	115.8 (19)	C15—C14—C3	121.0 (3)
N2—C5—N3	126.6 (3)	C19—C14—C3	119.3 (3)
N2—C5—C2	125.7 (3)	C16—C15—C14	119.9 (3)
N3—C5—C2	107.7 (2)	C16—C15—H15	119 (2)
N3—C6—H6A	109 (2)	C14—C15—H15	121 (2)
N3—C6—H6B	110.0 (19)	C17—C16—C15	120.3 (3)
H6A—C6—H6B	112 (3)	C17—C16—H16	121 (2)
N3—C6—H6C	108 (2)	C15—C16—H16	119 (2)
H6A—C6—H6C	112 (3)	C16—C17—C18	120.2 (3)
H6B—C6—H6C	106 (3)	C16—C17—H17	119 (2)
C8—C7—C12	118.4 (3)	C18—C17—H17	121 (2)
C8—C7—C1	120.9 (3)	C17—C18—C19	119.9 (3)
C12—C7—C1	120.7 (3)	C17—C18—H18	121 (2)
C9—C8—C7	120.9 (3)	C19—C18—H18	119 (3)
C9—C8—H8	118.9 (19)	C18—C19—C14	120.1 (3)
C7—C8—H8	120.1 (19)	C18—C19—H19	121 (2)
C10—C9—C8	119.6 (3)	C14—C19—H19	119 (2)
C10—C9—H9	120 (2)

C5—N3—N4—C1	−0.6 (3)	C2—C1—C7—C12	30.2 (5)
C6—N3—N4—C1	177.9 (3)	C12—C7—C8—C9	−0.7 (4)
N3—N4—C1—C2	−0.6 (3)	C1—C7—C8—C9	−178.7 (3)
N3—N4—C1—C7	175.7 (2)	C7—C8—C9—C10	−0.5 (4)
N4—C1—C2—C3	−173.5 (3)	C8—C9—C10—C11	0.8 (5)
C7—C1—C2—C3	10.8 (6)	C8—C9—C10—C13	−178.9 (3)
N4—C1—C2—C5	1.6 (3)	C9—C10—C11—C12	0.2 (5)
C7—C1—C2—C5	−174.1 (3)	C13—C10—C11—C12	179.8 (3)
C4—N1—C3—C2	−4.5 (4)	C10—C11—C12—C7	−1.5 (5)
C4—N1—C3—C14	172.5 (3)	C8—C7—C12—C11	1.7 (4)
C5—C2—C3—N1	8.1 (4)	C1—C7—C12—C11	179.7 (3)
C1—C2—C3—N1	−177.2 (3)	C11—C10—C13—F3	161.7 (3)
C5—C2—C3—C14	−168.7 (3)	C9—C10—C13—F3	−18.7 (4)
C1—C2—C3—C14	5.9 (6)	C11—C10—C13—F2	39.8 (4)
C5—N2—C4—N1	5.2 (5)	C9—C10—C13—F2	−140.6 (3)
C3—N1—C4—N2	−2.7 (5)	C11—C10—C13—F1	−79.9 (4)
C4—N2—C5—N3	179.1 (3)	C9—C10—C13—F1	99.7 (4)
C4—N2—C5—C2	−0.6 (4)	N1—C3—C14—C15	51.8 (4)
N4—N3—C5—N2	−178.2 (3)	C2—C3—C14—C15	−131.3 (3)
C6—N3—C5—N2	3.4 (5)	N1—C3—C14—C19	−128.0 (3)
N4—N3—C5—C2	1.6 (3)	C2—C3—C14—C19	48.9 (4)
C6—N3—C5—C2	−176.8 (3)	C19—C14—C15—C16	−2.7 (5)
C3—C2—C5—N2	−5.7 (4)	C3—C14—C15—C16	177.5 (3)
C1—C2—C5—N2	177.9 (3)	C14—C15—C16—C17	2.7 (5)
C3—C2—C5—N3	174.6 (2)	C15—C16—C17—C18	−0.7 (5)
C1—C2—C5—N3	−1.9 (3)	C16—C17—C18—C19	−1.3 (5)
N4—C1—C7—C8	32.8 (4)	C17—C18—C19—C14	1.3 (5)
C2—C1—C7—C8	−151.9 (3)	C15—C14—C19—C18	0.7 (5)
N4—C1—C7—C12	−145.2 (3)	C3—C14—C19—C18	−179.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···N2ⁱ	0.96 (3)	2.66 (3)	3.588 (4)	162 (2)
C6—H6B···N1ⁱⁱ	1.01 (4)	2.64 (3)	3.346 (4)	127 (2)

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

Funding information

The support of NSF–MRI grant No.1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

References

Bektemirov, T. A., Chekunova, E. V., Korbukh, I. A., Bulychev, Y. N., Yakunina, N. G. & Preobrazhenskaya, M. N. (1981). Acta Virol. 25, 326–329. Google Scholar
Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2016). APEX3, SAINT and SADABS . Bruker AXS, Inc., Madison, Wisconsin, USA. Google Scholar
El Hafi, M., Naas, M., Loubidi, M., Jouha, J., Ramli, Y., Mague, J. T., Essassi, E. M. & Guillaumet, G. (2017). C. R. Chim. 20, 927–933. Web of Science CSD CrossRef CAS Google Scholar
Rostamizadeh, S., Nojavan, M., Aryan, R., Sadeghian, H. & Davoodnejad, M. (2013). Chin. Chem. Lett. 24, 629–632. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008a). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008b). CELL_NOW. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2009). TWINABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Tintori, C., Fallacara, A. L., Radi, M., Zamperini, C., Dreassi, E., Crespan, E., Maga, G., Schenone, S., Musumeci, F., Brullo, C., Richters, A., Gasparrini, F., Angelucci, A., Festuccia, C., Delle Monache, S., Rauh, D. & Botta, M. (2015). J. Med. Chem. 58, 347–361. Web of Science CrossRef Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.