Crystal structure of 1,5-diethyl-3′,5′-di­phenyl-1,5-di­hydro-3′H-spiro­[pyra­zolo[3,4-d]pyrimidine-4,2′-[1,3,4]thia­diazole]

El Fal, M.; Ramli, Y.; Essassi, E.M.; Saadi, M.; El Ammari, L.

doi:10.1107/S2056989015017405

organic compounds

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ISSN: 2056-9890

Volume 71| Part 10| October 2015| Pages o769-o770

doi:10.1107/S2056989015017405

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Crystal structure of 1,5-diethyl-3′,5′-diphenyl-1,5-dihydro-3′H-spiro[pyrazolo[3,4-d]pyrimidine-4,2′-[1,3,4]thiadiazole]

Mohammed El Fal,^a Youssef Ramli,^b El Mokhtar Essassi,^a ^* Mohamed Saadi ^c and Lahcen El Ammari ^c

^aLaboratoire de Chimie Organique Hétérocyclique URAC 21, 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, University Mohammed V, Rabat, Morocco, and ^cLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
^*Correspondence e-mail: em_essassi@yahoo.fr

Edited by E. R. T. Tiekink, University of Malaya, Malaysia (Received 16 September 2015; accepted 17 September 2015; online 26 September 2015)

In the title compound, C₂₂H₂₂N₆S, the pyrazolo[3,4-d]pyrimidine rings system is almost planar, with the r.m.s. deviation for the fitted atoms being 0.011 Å. The two phenyl groups linked to the thiadiazole ring are nearly perpendicular to the fused-ring system as indicated by the dihedral angles of 86.93 (10) and 83.35 (11)°. However, the phenyl rings are almost coplanar with the thiadiazole ring (r.m.s. deviation = 0.015 Å), forming dihedral angles of 10.44 (11) and 10.06 (12)°. In the crystal, molecules are connected into a supramolecular layer in the ac plane via C—H⋯π interactions.

Keywords: crystal structure; pyrazolo[3,4-d]pyrimidine; thiadiazole.

CCDC reference: 1425539

1. Related literature

For biological properties of pyrazolo[3,4-d]pyrimidine derivatives, see: Chern et al. (2004 ); Schenone et al. (2009 ); Dinér et al. (2012 ); Taliani et al. (2010 ); Trivedi et al. (2012 ). For related structures, see: El Fal et al. (2014 , 2015 ); Ahoya et al. (2011 ); Anothane et al. (2012 ).

2. Experimental

2.1. Crystal data

C₂₂H₂₂N₆S
M_r = 402.51
Orthorhombic, P b c a
a = 14.501 (5) Å
b = 22.898 (5) Å
c = 12.468 (4) Å
V = 4140 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 296 K
0.37 × 0.34 × 0.29 mm

2.2. Data collection

Bruker X8 APEX diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.589, T_max = 0.746
25025 measured reflections
4224 independent reflections
2566 reflections with I > 2σ(I)
R_int = 0.079

2.3. Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.138
S = 1.00
4224 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C17–C22 and C11–C16 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯Cg1ⁱ	0.93	2.75	3.615 (3)	155
C20—H20⋯Cg2ⁱⁱ	0.93	2.77	3.564 (4)	144
Symmetry codes: (i) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL2013.

Supporting information

CCDC reference: 1425539

Crystal structure: contains datablock I. DOI: 10.1107/S2056989015017405/tk5387sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015017405/tk5387Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015017405/tk5387Isup3.cml

checkCIF report

Comment top

The pyrazolo[3,4-d]pyrimidine nucleus is considered as a very interesting and versatile scaffold for the synthesis of potential drug candidates acting on a wide range of biological targets (Schenone et al., 2009). Among their many applications, they have been used as kinase inhibitors (Dinér et al., 2012), antiviral agents (Chern et al., 2004), adenosine antagonists (Taliani et al., 2010 and as antitubercular agents (Trivedi et al., 2012). In the search for new compounds with therapeutic interest, we have prepared spiro[pyrazolo[3,4-d]pyrimidine-1,2'-[1,3,4]thiadiazole] derivatives via 1,3-dipolar cycloaddition using diphenyl hydrazonoyl chloride as the precursor for diphenyl nitrilimine, and 1,5-diethyl-1H-pyrazolo [3,4-d]pyrimidin-4(5H)-thione as the dipolarophile (El Fal et al., 2014; El Fal et al., 2015; Ahoya et al., 2011, Anothane et al., 2012).

The molecule of the title compound is built up from two fused five- and six-membered heterocycles linked to two ethyls and to two phenyl rings via the thiadiazole ring as shown in Fig. 1. The pyrazolo[3,4-d]pyrimidine system is virtually planar with the largest deviation from the mean plane being 0.016 (2) Å at N3 and makes dihedral angles of 86.93 (10) and 83.35 (11)° with the mean plane through the first (C11 to C16) and the second (C17 to C22) phenyl rings, respectively. Furthermore, the two phenyl rings are virtually coplanar with the largest deviation from the mean plane of -0.069 (2) Å, and makes a dihedral angle of 9.88 (9)° with the thiadiazole ring. No classic hydrogen bonds are observed in the structure.

Related literature top

For biological properties of pyrazolo[3,4-d]pyrimidine derivatives, see: Chern et al. (2004); Schenone et al. (2009); Dinér et al. (2012); Taliani et al. (2010); Trivedi et al. (2012). For related structures, see: El Fal et al. (2014, 2015); Ahoya et al. (2011); Anothane et al. (2012).

Experimental top

To a solution of 1,5-diethyl-1H-pyrazolo [3,4-d] pyrimidin-4(5H)–thione (2.08 g, 10 mmol) and diphenyl hydrazonoyl chloride (3.00 g, 13 mmol) in THF (30 ml) was added triethylamine (2 ml). The mixture was refluxed for 24 h. The precipitate was collected by filtration and was separated by silica gel chromatography (hexane/ethyl acetate: 8/2). The solid obtained was recrystallized from ethanol to afford the title compound as yellow crystals (yield: 60%; m.p. = 468 K).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXL2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015).

Figures top

Fig. 1. Molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles.

1,5-Diethyl-3',5'-diphenyl-1,5-dihydro-3'H-spiro[pyrazolo[3,4-d]pyrimidine-4,2'-[1,3,4]thiadiazole] top

Crystal data top

C₂₂H₂₂N₆S	D_x = 1.292 Mg m⁻³
M_r = 402.51	Melting point: 468 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
a = 14.501 (5) Å	Cell parameters from 4224 reflections
b = 22.898 (5) Å	θ = 2.3–26.4°
c = 12.468 (4) Å	µ = 0.18 mm⁻¹
V = 4140 (2) Å³	T = 296 K
Z = 8	Block, yellow
F(000) = 1696	0.37 × 0.34 × 0.29 mm

Data collection top

Bruker X8 APEX diffractometer	4224 independent reflections
Radiation source: fine-focus sealed tube	2566 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.079
φ and ω scans	θ_max = 26.4°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −18→17
T_min = 0.589, T_max = 0.746	k = −24→28
25025 measured reflections	l = −15→15

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.138	w = 1/[σ²(F_o²) + (0.0625P)² + 0.732P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
4224 reflections	Δρ_max = 0.31 e Å⁻³
262 parameters	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₂H₂₂N₆S	V = 4140 (2) Å³
M_r = 402.51	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 14.501 (5) Å	µ = 0.18 mm⁻¹
b = 22.898 (5) Å	T = 296 K
c = 12.468 (4) Å	0.37 × 0.34 × 0.29 mm

Data collection top

Bruker X8 APEX diffractometer	4224 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2566 reflections with I > 2σ(I)
T_min = 0.589, T_max = 0.746	R_int = 0.079
25025 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.00	Δρ_max = 0.31 e Å⁻³
4224 reflections	Δρ_min = −0.30 e Å⁻³
262 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.

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

	x	y	z	U_iso*/U_eq
C1	0.48041 (15)	0.16398 (10)	0.52664 (19)	0.0383 (5)
C2	0.54607 (15)	0.07863 (9)	0.63901 (19)	0.0363 (5)
C3	0.49773 (15)	0.04386 (10)	0.72025 (19)	0.0373 (5)
C4	0.41299 (17)	0.04978 (11)	0.7732 (2)	0.0511 (7)
H4	0.3727	0.0809	0.7631	0.061*
C5	0.53365 (15)	−0.00752 (10)	0.75801 (19)	0.0377 (5)
C6	0.65913 (16)	−0.00200 (10)	0.6605 (2)	0.0413 (6)
H6	0.7162	−0.0164	0.6392	0.050*
C7	0.69620 (18)	0.07699 (12)	0.5361 (2)	0.0554 (7)
H7A	0.7560	0.0814	0.5700	0.066*
H7B	0.6733	0.1158	0.5199	0.066*
C8	0.7081 (3)	0.04447 (17)	0.4342 (3)	0.1022 (13)
H8A	0.7498	0.0654	0.3884	0.153*
H8B	0.6495	0.0406	0.3992	0.153*
H8C	0.7327	0.0064	0.4492	0.153*
C9	0.4750 (2)	−0.08616 (13)	0.8837 (3)	0.0726 (9)
H9A	0.4554	−0.0814	0.9576	0.087*
H9B	0.5377	−0.1009	0.8841	0.087*
C10	0.4139 (3)	−0.12911 (14)	0.8295 (3)	0.0962 (13)
H10A	0.4166	−0.1657	0.8668	0.144*
H10B	0.4340	−0.1345	0.7568	0.144*
H10C	0.3517	−0.1148	0.8298	0.144*
C11	0.61067 (15)	0.15818 (10)	0.76316 (19)	0.0383 (6)
C12	0.66082 (17)	0.11905 (11)	0.8257 (2)	0.0478 (6)
H12	0.6632	0.0797	0.8072	0.057*
C13	0.70698 (17)	0.13906 (13)	0.9156 (2)	0.0538 (7)
H13	0.7404	0.1128	0.9571	0.065*
C14	0.70444 (18)	0.19696 (13)	0.9449 (2)	0.0576 (8)
H14	0.7357	0.2099	1.0054	0.069*
C15	0.65481 (18)	0.23514 (13)	0.8829 (2)	0.0577 (8)
H15	0.6524	0.2744	0.9021	0.069*
C16	0.60827 (16)	0.21655 (11)	0.7924 (2)	0.0479 (7)
H16	0.5753	0.2432	0.7512	0.058*
C17	0.43453 (15)	0.20319 (10)	0.4501 (2)	0.0399 (6)
C18	0.39468 (17)	0.18210 (12)	0.3574 (2)	0.0505 (7)
H18	0.3970	0.1423	0.3424	0.061*
C19	0.35137 (19)	0.21958 (14)	0.2866 (2)	0.0623 (8)
H19	0.3252	0.2051	0.2239	0.075*
C20	0.3471 (2)	0.27838 (14)	0.3090 (3)	0.0665 (9)
H20	0.3182	0.3037	0.2614	0.080*
C21	0.38543 (19)	0.29943 (13)	0.4014 (3)	0.0646 (8)
H21	0.3823	0.3392	0.4165	0.077*
C22	0.42870 (18)	0.26235 (11)	0.4724 (2)	0.0527 (7)
H22	0.4540	0.2771	0.5354	0.063*
N1	0.52713 (13)	0.18375 (8)	0.60593 (16)	0.0414 (5)
N2	0.56296 (14)	0.14038 (8)	0.67014 (16)	0.0444 (5)
N3	0.63253 (12)	0.04874 (8)	0.61271 (16)	0.0396 (5)
N4	0.61620 (13)	−0.03289 (9)	0.73112 (17)	0.0430 (5)
N5	0.47290 (14)	−0.02945 (9)	0.82976 (18)	0.0523 (6)
N6	0.39730 (15)	0.00565 (10)	0.8391 (2)	0.0618 (7)
S1	0.47272 (5)	0.08793 (3)	0.51716 (6)	0.0486 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0362 (12)	0.0355 (13)	0.0431 (14)	0.0013 (10)	−0.0001 (11)	0.0032 (11)
C2	0.0380 (12)	0.0283 (12)	0.0425 (14)	0.0008 (10)	−0.0069 (10)	−0.0008 (10)
C3	0.0362 (12)	0.0305 (12)	0.0453 (15)	0.0006 (10)	−0.0020 (10)	−0.0003 (11)
C4	0.0440 (14)	0.0471 (16)	0.0621 (19)	0.0096 (12)	0.0070 (12)	0.0006 (14)
C5	0.0365 (12)	0.0331 (13)	0.0435 (14)	−0.0019 (10)	−0.0020 (10)	0.0033 (11)
C6	0.0332 (12)	0.0411 (14)	0.0496 (15)	0.0055 (11)	−0.0048 (11)	−0.0022 (12)
C7	0.0491 (15)	0.0602 (18)	0.0568 (19)	−0.0083 (13)	0.0078 (12)	0.0152 (15)
C8	0.127 (3)	0.107 (3)	0.073 (3)	−0.015 (2)	0.048 (2)	−0.004 (2)
C9	0.070 (2)	0.066 (2)	0.082 (2)	0.0031 (17)	0.0156 (17)	0.0367 (18)
C10	0.118 (3)	0.054 (2)	0.117 (3)	−0.008 (2)	0.038 (3)	0.014 (2)
C11	0.0373 (12)	0.0403 (14)	0.0372 (14)	−0.0053 (10)	0.0004 (10)	−0.0034 (11)
C12	0.0557 (15)	0.0409 (15)	0.0469 (16)	−0.0021 (13)	−0.0091 (12)	0.0008 (12)
C13	0.0506 (15)	0.068 (2)	0.0425 (16)	−0.0036 (14)	−0.0098 (12)	0.0037 (14)
C14	0.0461 (15)	0.075 (2)	0.0516 (18)	−0.0088 (15)	−0.0046 (12)	−0.0178 (15)
C15	0.0515 (15)	0.0553 (18)	0.066 (2)	−0.0024 (14)	−0.0024 (14)	−0.0238 (15)
C16	0.0451 (14)	0.0396 (15)	0.0591 (18)	0.0003 (11)	−0.0071 (12)	−0.0098 (13)
C17	0.0360 (12)	0.0388 (14)	0.0449 (15)	0.0055 (11)	0.0022 (10)	0.0085 (11)
C18	0.0537 (15)	0.0487 (16)	0.0491 (17)	0.0087 (13)	−0.0019 (13)	0.0070 (13)
C19	0.0596 (17)	0.074 (2)	0.0532 (19)	0.0092 (15)	−0.0122 (14)	0.0101 (16)
C20	0.0640 (18)	0.061 (2)	0.074 (2)	0.0148 (16)	−0.0108 (16)	0.0262 (17)
C21	0.0640 (18)	0.0450 (17)	0.085 (2)	0.0131 (14)	−0.0074 (17)	0.0128 (16)
C22	0.0547 (15)	0.0406 (16)	0.0627 (19)	0.0054 (13)	−0.0086 (13)	0.0080 (13)
N1	0.0478 (11)	0.0308 (11)	0.0457 (12)	0.0023 (9)	−0.0042 (10)	0.0065 (9)
N2	0.0595 (13)	0.0278 (11)	0.0461 (13)	−0.0011 (9)	−0.0168 (10)	0.0046 (9)
N3	0.0373 (10)	0.0369 (11)	0.0446 (12)	−0.0005 (9)	0.0006 (8)	0.0041 (9)
N4	0.0377 (11)	0.0395 (12)	0.0519 (14)	0.0061 (9)	−0.0012 (9)	0.0091 (10)
N5	0.0481 (12)	0.0468 (13)	0.0619 (15)	0.0026 (10)	0.0098 (11)	0.0169 (11)
N6	0.0516 (13)	0.0624 (16)	0.0714 (17)	0.0052 (12)	0.0180 (12)	0.0111 (13)
S1	0.0567 (4)	0.0362 (4)	0.0531 (4)	−0.0001 (3)	−0.0217 (3)	0.0025 (3)

Geometric parameters (Å, º) top

C1—N1	1.281 (3)	C10—H10B	0.9600
C1—C17	1.469 (3)	C10—H10C	0.9600
C1—S1	1.749 (2)	C11—C16	1.386 (3)
C2—N3	1.466 (3)	C11—C12	1.393 (3)
C2—C3	1.467 (3)	C11—N2	1.411 (3)
C2—N2	1.487 (3)	C12—C13	1.383 (3)
C2—S1	1.867 (2)	C12—H12	0.9300
C3—C5	1.370 (3)	C13—C14	1.376 (4)
C3—C4	1.401 (3)	C13—H13	0.9300
C4—N6	1.323 (3)	C14—C15	1.371 (4)
C4—H4	0.9300	C14—H14	0.9300
C5—N5	1.352 (3)	C15—C16	1.381 (4)
C5—N4	1.372 (3)	C15—H15	0.9300
C6—N4	1.290 (3)	C16—H16	0.9300
C6—N3	1.361 (3)	C17—C18	1.379 (4)
C6—H6	0.9300	C17—C22	1.386 (3)
C7—N3	1.478 (3)	C18—C19	1.382 (4)
C7—C8	1.482 (4)	C18—H18	0.9300
C7—H7A	0.9700	C19—C20	1.377 (4)
C7—H7B	0.9700	C19—H19	0.9300
C8—H8A	0.9600	C20—C21	1.368 (4)
C8—H8B	0.9600	C20—H20	0.9300
C8—H8C	0.9600	C21—C22	1.378 (4)
C9—N5	1.463 (3)	C21—H21	0.9300
C9—C10	1.486 (5)	C22—H22	0.9300
C9—H9A	0.9700	N1—N2	1.377 (3)
C9—H9B	0.9700	N5—N6	1.364 (3)
C10—H10A	0.9600

N1—C1—C17	121.6 (2)	C12—C11—N2	122.1 (2)
N1—C1—S1	115.96 (18)	C13—C12—C11	119.6 (2)
C17—C1—S1	122.39 (18)	C13—C12—H12	120.2
N3—C2—C3	108.05 (18)	C11—C12—H12	120.2
N3—C2—N2	111.20 (18)	C14—C13—C12	121.4 (3)
C3—C2—N2	114.5 (2)	C14—C13—H13	119.3
N3—C2—S1	111.02 (16)	C12—C13—H13	119.3
C3—C2—S1	110.59 (15)	C15—C14—C13	118.6 (3)
N2—C2—S1	101.41 (14)	C15—C14—H14	120.7
C5—C3—C4	104.8 (2)	C13—C14—H14	120.7
C5—C3—C2	121.5 (2)	C14—C15—C16	121.3 (3)
C4—C3—C2	133.8 (2)	C14—C15—H15	119.3
N6—C4—C3	111.7 (2)	C16—C15—H15	119.3
N6—C4—H4	124.2	C15—C16—C11	120.0 (3)
C3—C4—H4	124.2	C15—C16—H16	120.0
N5—C5—C3	107.4 (2)	C11—C16—H16	120.0
N5—C5—N4	124.9 (2)	C18—C17—C22	119.0 (2)
C3—C5—N4	127.7 (2)	C18—C17—C1	121.3 (2)
N4—C6—N3	129.0 (2)	C22—C17—C1	119.6 (2)
N4—C6—H6	115.5	C17—C18—C19	120.6 (3)
N3—C6—H6	115.5	C17—C18—H18	119.7
N3—C7—C8	114.0 (2)	C19—C18—H18	119.7
N3—C7—H7A	108.8	C20—C19—C18	119.9 (3)
C8—C7—H7A	108.8	C20—C19—H19	120.1
N3—C7—H7B	108.8	C18—C19—H19	120.1
C8—C7—H7B	108.8	C21—C20—C19	119.8 (3)
H7A—C7—H7B	107.6	C21—C20—H20	120.1
C7—C8—H8A	109.5	C19—C20—H20	120.1
C7—C8—H8B	109.5	C20—C21—C22	120.6 (3)
H8A—C8—H8B	109.5	C20—C21—H21	119.7
C7—C8—H8C	109.5	C22—C21—H21	119.7
H8A—C8—H8C	109.5	C21—C22—C17	120.1 (3)
H8B—C8—H8C	109.5	C21—C22—H22	120.0
N5—C9—C10	111.5 (3)	C17—C22—H22	120.0
N5—C9—H9A	109.3	C1—N1—N2	113.15 (19)
C10—C9—H9A	109.3	N1—N2—C11	117.04 (18)
N5—C9—H9B	109.3	N1—N2—C2	118.15 (18)
C10—C9—H9B	109.3	C11—N2—C2	124.77 (19)
H9A—C9—H9B	108.0	C6—N3—C2	122.90 (19)
C9—C10—H10A	109.5	C6—N3—C7	118.6 (2)
C9—C10—H10B	109.5	C2—N3—C7	118.34 (19)
H10A—C10—H10B	109.5	C6—N4—C5	110.84 (19)
C9—C10—H10C	109.5	C5—N5—N6	111.18 (19)
H10A—C10—H10C	109.5	C5—N5—C9	128.3 (2)
H10B—C10—H10C	109.5	N6—N5—C9	120.0 (2)
C16—C11—C12	119.1 (2)	C4—N6—N5	105.0 (2)
C16—C11—N2	118.9 (2)	C1—S1—C2	91.28 (10)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the ring centroids of the C17–C22 and C11–C16 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···Cg1ⁱ	0.93	2.75	3.615 (3)	155
C20—H20···Cg2ⁱⁱ	0.93	2.77	3.564 (4)	144

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

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the ring centroids of the C17–C22 and C11–C16 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···Cg1ⁱ	0.93	2.75	3.615 (3)	155
C20—H20···Cg2ⁱⁱ	0.93	2.77	3.564 (4)	144

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

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements, and the University Mohammed V, Rabat, Morocco, for financial support.

References

Ahoya, C. A., Daouda, B., Bouhfid, R., Hançali, A., Bousmina, M., Zerzouf, A., El Aouad, R. & Essassi, E. M. (2011). Arkivoc, (ii), 217–226. Google Scholar
Anothane, C. A., Bouhfid, R., Essassi, E. M. & Ng, S. W. (2012). Acta Cryst. E68, o103. CSD CrossRef IUCr Journals Google Scholar
Bruker (2009). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chern, J.-H., Shia, K.-S., Hsu, T.-A., Tai, C.-L., Lee, C.-C., Lee, Y.-C., Chang, C.-S., Tseng, S.-N. & Shih, S.-R. (2004). Bioorg. Med. Chem. Lett. 14, 2519–2525. CrossRef PubMed CAS Google Scholar
Dinér, P., Alao, J. P., Söderlund, J., Sunnerhagen, P. & Grøtli, M. (2012). J. Med. Chem. 55, 4872–4876. PubMed Google Scholar
El Fal, M., Ramli, Y., Essassi, E. M., Saadi, M. & El Ammari, L. (2014). Acta Cryst. E70, o1038. CSD CrossRef IUCr Journals Google Scholar
El Fal, M., Ramli, Y., Essassi, E. M., Saadi, M. & El Ammari, L. (2015). Acta Cryst. E71, o95–o96. CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Schenone, S., Bruno, O., Radi, M. & Botta, M. (2009). Mini-Rev. Org. Chem. 6, 220–233. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Taliani, S., La Motta, C., Mugnaini, L., Simorini, F., Salerno, S., Marini, A. M., Da Settimo, F., Cosconati, S., Cosimelli, B. & Greco, G. (2010). J. Med. Chem. 53, 3954–3963. CrossRef CAS PubMed Google Scholar
Trivedi, A. R., Dholariya, B. H., Vakhariya, C. P., Dodiya, D. K., Ram, H. K., Kataria, V. B., Siddiqui, A. B. & Shah, V. H. (2012). Med. Chem. Res. 21, 1887–1891. CrossRef CAS Google Scholar

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Volume 71| Part 10| October 2015| Pages o769-o770

doi:10.1107/S2056989015017405

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 1,5-di­ethyl-3′,5′-di­phenyl-1,5-di­hydro-3′H-spiro­[pyra­zolo[3,4-d]pyrimidine-4,2′-[1,3,4]thia­diazole]

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 1,5-diethyl-3′,5′-diphenyl-1,5-dihydro-3′H-spiro[pyrazolo[3,4-d]pyrimidine-4,2′-[1,3,4]thiadiazole]