1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-aminium chloride–thio­urea (1/1)

Shahzad Murtaza; Muhammad Hamza; M Nawaz Tahir

doi:10.1107/S1600536811029989

. 2011 Jul 30;67(Pt 8):o2193. doi: 10.1107/S1600536811029989

1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-aminium chloride–thiourea (1/1)

Shahzad Murtaza ^a, Muhammad Hamza ^a, M Nawaz Tahir ^b,^*

PMCID: PMC3213624 PMID: 22091201

Abstract

In the title compound, C₁₁H₁₄N₃O⁺·Cl⁻·CH₄N₂S, the components are connected into a two-dimensional polymeric structure parallel to (001) via N—H⋯Cl, N—H⋯O, N—H⋯S and C—H⋯S hydrogen bonds. The dihedral angle between the phenyl and 2,3-dihydro-1H-pyrazole rings is 44.96 (7)°.

Related literature

For the structure of 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol- 4-aminium 2-hydroxybenzoate, see: Chitradevi et al. (2009 ▶).

Experimental

Crystal data

C₁₁H₁₄N₃O⁺·Cl⁻·CH₄N₂S
M _r = 315.82
Monoclinic,
a = 9.9733 (11) Å
b = 8.2572 (8) Å
c = 18.859 (2) Å
β = 90.851 (4)°
V = 1552.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 296 K
0.30 × 0.15 × 0.14 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.935, T _max = 0.950
14413 measured reflections
3876 independent reflections
2948 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.111
S = 1.02
3876 reflections
192 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811029989/gk2395sup1.cif

e-67-o2193-sup1.cif^{(23.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029989/gk2395Isup2.hkl

e-67-o2193-Isup2.hkl^{(186.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811029989/gk2395Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯S1ⁱ	0.92 (2)	2.28 (2)	3.1619 (17)	159.9 (19)
N3—H3B⋯O1ⁱⁱ	0.90 (2)	1.87 (2)	2.764 (2)	174 (2)
N3—H3C⋯Cl1ⁱⁱⁱ	0.952 (19)	2.08 (2)	3.0316 (16)	180 (2)
N4—H4A⋯Cl1	0.86	2.41	3.2404 (17)	163
N4—H4B⋯O1^iv	0.86	2.12	2.970 (2)	170
N5—H5A⋯Cl1	0.86	2.74	3.4956 (19)	148
N5—H5A⋯S1^v	0.86	2.87	3.3768 (17)	120
N5—H5B⋯Cl1^vi	0.86	2.56	3.4091 (18)	171
C10—H10B⋯S1^vi	0.96	2.85	3.505 (2)	126

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .

Acknowledgments

The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, former Vice Chancellor, University of Sargodha, Pakistan. The authors also acknowledge the technical support provided by Bana International, Karachi, Pakistan.

supplementary crystallographic information

Comment

The crystal structure of 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol- 4-aminium 2-hydroxybenzoate (Chitradevi et al., 2009) has been published which is related to the title compound (Fig. 1).

The asymmetric unit of title compound consists of three components: 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-aminium cation, chloride ion and thiourea molecule. In cation the phenyl ring A (C1—C6) and 2,3-dihydro-1H-pyrazole ring B (N1/N2/C7/C8/C9) are planar with r. m. s. deviations of 0.005 and 0.020 Å. The dihedral angle between A/B is 44.96 (7)°. The attached atoms O1, N3, C10 and C11 are at a distance of -0.122 (3), 0.005 (3), 0.034 (3) and 0.513 (3) Å respectively, from the mean plane of B. The thiourea molecule (S1/C12/N4/N5) is planar with r.m.s. deviations of 0.003 Å. There exist intermolecular hydrogen bonds of N–H···Cl, N–H···O, N–H···S and C–H···S types (Table 1, Fig. 2). The crystal components are connected by hydrogen bonds into infinite two dimensional polymeric network parallel to (0 0 1)

Experimental

4-Aminophenazone (0.203 g, 1.0 mmol) and thiourea (0.076 g, 1.0 mmol) were dissolved in ethanol (15 ml) and the mixture was acidified by 1 N HCl. The mixture was refluxed for one hour and solvent was evaporated on rotary evaporator to almost dryness. The crude product was recrystallized from ethanol yielding light yellow needles of the title compound.