3,5-Di-tert-butyl-1H-pyrazole-4-carbo­nitrile

Zhao, N.; Akwataghibe, K.; Pompilius, A.; Shelly, E.

doi:10.1107/S2414314616006738

organic compounds

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ISSN: 2414-3146

Volume 1| Part 4| April 2016| x160673

doi:10.1107/S2414314616006738

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3,5-Di-tert-butyl-1H-pyrazole-4-carbonitrile

Ningfeng Zhao,^a ^* Kelechi Akwataghibe,^a Arielle Pompilius ^a and Everett Shelly ^a

^aDepartment of Chemistry, Jacksonville University, Jacksonville, FL 32211, USA
^*Correspondence e-mail: pzhao@ju.edu

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 13 April 2016; accepted 20 April 2016; online 22 April 2016)

In the title compound, C₁₂H₁₉N₃, the cyano group lies in the plane of the pyrazole ring, and has a linear C—C N bond angle of 179.2 (1)°. The NH H atom of the pyrazole ring is disordered equally over the two ring N atoms. In the crystal, molecules are linked via N—H⋯N hydrogen bonds, forming inversion dimers with an R₂²(6) ring motif.

Keywords: crystal structure; cyanopyrazole; carbonitrile; symmetrically substituted; N—H⋯N hydrogen bonds; inversion dimers.

CCDC reference: 1475402

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Chemical scheme

Structure description

The title compound, represents the first symmetrically substituted 4-carbonitrile pyrazole, and was prepared as a precursor for the preparation of scorpionate ligands. In the title compound, Fig. 1, the NH H atom is disordered across the two N atoms (N2 and N3) of the pyrazole ring. The carbonitrile unit, C2—C1 N1, lies in the plane of the pyrazole ring and deviates only slightly from linearity with a bond angle of 179.2 (1)°.

Figure 1
A view of the molecular structure of the title compound, showing the atom labeling. Displacement ellipsoids are drawn at the 50% probability level. The two positions of the disordered NH H atoms are shown, with hashed bonds.

In the crystal, molecules are linked by pairs of N—H⋯N hydrogen bonds, forming inversion dimers with an $[R_{2}^{2}]$ (6) ring motif (Fig. 2 and Table 1). There are no other significant intermolecular interactions present.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N3ⁱ	0.86 (3)	2.23 (3)	2.9232 (14)	138 (2)
N3—H3⋯N2ⁱ	0.85 (3)	2.19 (3)	2.9232 (14)	144 (2)
Symmetry code: (i) -x+1, -y+2, -z+1.

Figure 2
A view along the b axis of the crystal packing of the title compound. The N—H⋯N hydrogen bonds are shown as dashed lines. Only one disordered NH H atom is shown and all C-bound H atoms have been omitted for clarity.

Synthesis and crystallization

Sodium hydride (0.69 g, 17.24 mmol, 60% dispersion in mineral oil) was added to 100 ml of dry toluene in an ice bath forming a suspension. Trimethylacetylacetonitrile (2.16 g, 17.24 mmol) was added to this suspension, resulting in the immediate appearance of bubbles. The mixture was stirred for 18 h before trimethylacetyl chloride (2.08 g, 17.24 mmol) was added. The reaction mixture was stirred overnight followed by three extractions using 100 ml of 0.2 M NaOH solution each time. The aqueous layers were combined and acidified with an HCl/H₂O (50/50) solution to pH1. A white precipitate appeared immediately and was extracted with three portions of 100 ml of ethyl acetate. Removal of the solvent under reduced pressure yielded 2.15 g (10.29 mmol, yield 59.67%) of the crude product, which was recrystallized from ethanol to give 4-cyano-2,2,6,6-tetramethyl-3,5-heptanedione (1.07 g, 5.12 mmol, 29.70%). This diketone compound was then reacted with hydrazine monohydrate (0.26 g, 5.12 mmol) in 100 ml of methanol and stirred overnight. The solvent was removed under reduced pressure to yield the crude product of the title compound as a white solid (0.93 g, 4.54 mmol, 26.31%). X-ray quality crystals were obtained by slow evaporation of a solution in ethanol at room temperature (0.66 g, 3.22 mmol, 18.67%).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The NH H atom was located in a difference Fourier map and found to be disordered equally across the two N atoms (N2 and N3) of the pyrazole ring. These two H atoms (H2 and H3) were freely refined with an occupancy of 0.5 each.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₂H₁₉N₃
M_r	205.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	10.5993 (3), 9.7641 (3), 12.4435 (4)
β (°)	109.065 (1)
V (Å³)	1217.17 (6)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	0.53
Crystal size (mm)	0.15 × 0.10 × 0.09

Data collection
Diffractometer	Bruker D8 Platinum135
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.211, 0.320
No. of measured, independent and observed [I > 2σ(I)] reflections	11126, 2183, 2037
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.096, 1.05
No. of reflections	2183
No. of parameters	150
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.20
Computer programs: APEX3 and SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), Mercury (Macrae et al., 2008 ) and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 1475402

Crystal structure: contains datablocks Global, I. DOI: 10.1107/S2414314616006738/su4036sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616006738/su4036Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616006738/su4036Isup3.cml

checkCIF report

Experimental top

Sodium hydride (0.69 g, 17.24 mmol, 60% dispersion in mineral oil) was added to 100 ml of dry toluene in an ice bath forming a suspension. Trimethylacetylacetonitrile (2.16 g, 17.24 mmol) was added to this suspension, resulting in the immediate appearance of bubbles. The mixture was stirred for 18 h before trimethylacetyl chloride (2.08 g, 17.24 mmol) was added. The reaction mixture was stirred overnight followed by three extractions using 100 ml of 0.2 M NaOH solution each time. The aqueous layers were combined and acidified with an HCl/H₂O (50/50) solution to pH~1. A white precipitate appeared immediately and was extracted with three portions of 100 ml of ethyl acetate. Removal of the solvent under reduced pressure yielded 2.15 g (10.29 mmol, yield 59.67%) of the crude product, which was recrystallized from ethanol to give 4-cyano-2,2,6,6-tetramethyl-3,5-heptanedione (1.07 g, 5.12 mmol, 29.70%). This diketone compound was then reacted with hydrazine monohydrate (0.26 g, 5.12 mmol) in 100 ml of methanol and stirred overnight. The solvent was removed under reduced pressure to yield the crude product of the title compound as a white solid (0.93 g, 4.54 mmol, 26.31%). X-ray quality crystals were obtained by slow evaporation of a solution in ethanol at room temperature (0.66 g, 3.22 mmol, 18.67%).

Structure description top

The title compound, represents the first symmetrically substituted 4-carbonitrile pyrazole, and was prepared as a precursor for the preparation of scorpionate ligands. In the title compound, Fig. 1, the NH H atom is disordered across the two N atoms (N2 and N3) of the pyrazole ring. The carbonitrile unit, C2—C1≡N1, lies in the plane of the pyrazole ring and deviates only slightly from linearity with a bond angle of 179.2 (1)°.

In the crystal, molecules are linked by pairs of N—H···N hydrogen bonds, forming inversion dimers with an R₂²(6) ring motif (Fig. 2 and Table 1). There are no other significant intermolecular interactions present.

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: SHELXL2014 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. A view of the molecular structure of the title compound, showing the atom labeling. Displacement ellipsoids are drawn at the 50% probability level. The two positions of the disordered NH H atoms are shown, with hashed bonds.
	Fig. 2. A view along the b axis of the crystal packing of the title compound. The N—H···N hydrogen bonds are shown as dashed lines. Only one disordered NH H atom is shown and all C-bound H atoms have been omitted for clarity.

3,5-Di-tert-butyl-1H-pyrazole-4-carbonitrile top

Crystal data top

C₁₂H₁₉N₃	F(000) = 448
M_r = 205.30	D_x = 1.120 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
a = 10.5993 (3) Å	Cell parameters from 7895 reflections
b = 9.7641 (3) Å	θ = 4.4–68.3°
c = 12.4435 (4) Å	µ = 0.53 mm⁻¹
β = 109.065 (1)°	T = 100 K
V = 1217.17 (6) Å³	Block, colourless
Z = 4	0.15 × 0.10 × 0.09 mm

Data collection top

Bruker D8 Platinum135 diffractometer	2183 independent reflections
Radiation source: Micro Focus Rotating Anode, Bruker FR-591	2037 reflections with I > 2σ(I)
Multilayer Mirrors monochromator	R_int = 0.040
Detector resolution: 7.9 pixels mm^-1	θ_max = 68.2°, θ_min = 4.4°
ω and φ scans	h = −10→12
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −11→11
T_min = 0.211, T_max = 0.320	l = −14→13
11126 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)] = 0.037	Hydrogen site location: mixed
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0453P)² + 0.4223P] where P = (F_o² + 2F_c²)/3
2183 reflections	(Δ/σ)_max < 0.001
150 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₂H₁₉N₃	V = 1217.17 (6) Å³
M_r = 205.30	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 10.5993 (3) Å	µ = 0.53 mm⁻¹
b = 9.7641 (3) Å	T = 100 K
c = 12.4435 (4) Å	0.15 × 0.10 × 0.09 mm
β = 109.065 (1)°

Data collection top

Bruker D8 Platinum135 diffractometer	2183 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2016)	2037 reflections with I > 2σ(I)
T_min = 0.211, T_max = 0.320	R_int = 0.040
11126 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.21 e Å⁻³
2183 reflections	Δρ_min = −0.19 e Å⁻³
150 parameters

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	Occ. (<1)
N1	0.75868 (11)	0.50824 (12)	0.79507 (11)	0.0384 (3)
N2	0.49278 (10)	0.84937 (10)	0.55771 (8)	0.0189 (2)
H2	0.425 (3)	0.897 (3)	0.520 (2)	0.020 (6)*	0.5
N3	0.61616 (9)	0.90020 (10)	0.56683 (8)	0.0182 (2)
H3	0.622 (2)	0.975 (3)	0.534 (2)	0.013 (6)*	0.5
C1	0.70672 (11)	0.59805 (12)	0.73785 (10)	0.0238 (3)
C2	0.64420 (11)	0.70939 (11)	0.66689 (9)	0.0172 (2)
C3	0.50608 (11)	0.73346 (11)	0.61695 (9)	0.0165 (2)
C4	0.70997 (11)	0.81784 (11)	0.63223 (9)	0.0160 (2)
C5	0.38860 (11)	0.65176 (11)	0.62665 (9)	0.0179 (3)
C6	0.25914 (12)	0.70092 (14)	0.53837 (11)	0.0289 (3)
H6A	0.2429	0.7966	0.5537	0.043*
H6B	0.1847	0.6441	0.5426	0.043*
H6C	0.2668	0.6936	0.4622	0.043*
C7	0.40648 (13)	0.49897 (13)	0.60832 (12)	0.0313 (3)
H7A	0.4089	0.4842	0.5311	0.047*
H7B	0.3317	0.4478	0.6185	0.047*
H7C	0.4903	0.4671	0.6636	0.047*
C8	0.38019 (13)	0.67309 (13)	0.74628 (10)	0.0283 (3)
H8A	0.4647	0.6455	0.8031	0.043*
H8B	0.3074	0.6174	0.7553	0.043*
H8C	0.3631	0.7700	0.7569	0.043*
C9	0.85791 (11)	0.84303 (11)	0.65776 (9)	0.0188 (3)
C10	0.88128 (12)	0.97784 (13)	0.60457 (10)	0.0251 (3)
H10A	0.8377	0.9740	0.5220	0.038*
H10B	0.9773	0.9923	0.6217	0.038*
H10C	0.8437	1.0537	0.6360	0.038*
C11	0.92803 (12)	0.84933 (12)	0.78699 (10)	0.0248 (3)
H11A	0.8899	0.9241	0.8191	0.037*
H11B	1.0236	0.8656	0.8030	0.037*
H11C	0.9153	0.7623	0.8214	0.037*
C12	0.91653 (12)	0.72457 (13)	0.60780 (11)	0.0295 (3)
H12A	0.9014	0.6379	0.6414	0.044*
H12B	1.0126	0.7389	0.6249	0.044*
H12C	0.8729	0.7214	0.5252	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0241 (6)	0.0312 (6)	0.0507 (7)	−0.0030 (5)	−0.0004 (5)	0.0191 (5)
N2	0.0160 (5)	0.0200 (5)	0.0209 (5)	−0.0003 (4)	0.0062 (4)	0.0026 (4)
N3	0.0150 (5)	0.0202 (5)	0.0191 (5)	0.0002 (4)	0.0052 (4)	0.0033 (4)
C1	0.0171 (6)	0.0230 (6)	0.0285 (6)	−0.0030 (4)	0.0036 (5)	0.0048 (5)
C2	0.0168 (6)	0.0171 (5)	0.0168 (5)	0.0005 (4)	0.0042 (4)	0.0015 (4)
C3	0.0174 (6)	0.0170 (5)	0.0150 (5)	−0.0010 (4)	0.0052 (4)	−0.0010 (4)
C4	0.0160 (6)	0.0173 (5)	0.0144 (5)	0.0004 (4)	0.0047 (4)	−0.0010 (4)
C5	0.0158 (6)	0.0182 (6)	0.0202 (6)	−0.0019 (4)	0.0065 (4)	0.0005 (4)
C6	0.0171 (6)	0.0366 (7)	0.0307 (7)	−0.0043 (5)	0.0047 (5)	0.0086 (5)
C7	0.0244 (7)	0.0213 (6)	0.0510 (8)	−0.0056 (5)	0.0161 (6)	−0.0072 (5)
C8	0.0332 (7)	0.0303 (7)	0.0258 (6)	−0.0101 (5)	0.0153 (5)	−0.0012 (5)
C9	0.0139 (5)	0.0209 (6)	0.0212 (6)	0.0002 (4)	0.0050 (4)	0.0016 (4)
C10	0.0179 (6)	0.0279 (6)	0.0294 (6)	−0.0025 (4)	0.0074 (5)	0.0059 (5)
C11	0.0184 (6)	0.0280 (6)	0.0240 (6)	−0.0025 (5)	0.0015 (5)	0.0027 (5)
C12	0.0220 (6)	0.0307 (7)	0.0388 (7)	0.0029 (5)	0.0142 (5)	−0.0035 (5)

Geometric parameters (Å, º) top

N1—C1	1.1502 (16)	C7—H7B	0.9800
N2—H2	0.86 (3)	C7—H7C	0.9800
N2—N3	1.3683 (13)	C8—H8A	0.9800
N2—C3	1.3328 (14)	C8—H8B	0.9800
N3—H3	0.85 (3)	C8—H8C	0.9800
N3—C4	1.3301 (14)	C9—C10	1.5295 (16)
C1—C2	1.4207 (16)	C9—C11	1.5366 (16)
C2—C3	1.4107 (15)	C9—C12	1.5372 (16)
C2—C4	1.4107 (15)	C10—H10A	0.9800
C3—C5	1.5165 (15)	C10—H10B	0.9800
C4—C9	1.5148 (15)	C10—H10C	0.9800
C5—C6	1.5281 (16)	C11—H11A	0.9800
C5—C7	1.5303 (16)	C11—H11B	0.9800
C5—C8	1.5343 (15)	C11—H11C	0.9800
C6—H6A	0.9800	C12—H12A	0.9800
C6—H6B	0.9800	C12—H12B	0.9800
C6—H6C	0.9800	C12—H12C	0.9800
C7—H7A	0.9800

N3—N2—H2	117.6 (18)	H7A—C7—H7C	109.5
C3—N2—H2	132.6 (18)	H7B—C7—H7C	109.5
C3—N2—N3	109.67 (9)	C5—C8—H8A	109.5
N2—N3—H3	119.1 (17)	C5—C8—H8B	109.5
C4—N3—N2	109.55 (9)	C5—C8—H8C	109.5
C4—N3—H3	131.3 (17)	H8A—C8—H8B	109.5
N1—C1—C2	179.21 (13)	H8A—C8—H8C	109.5
C3—C2—C1	127.41 (10)	H8B—C8—H8C	109.5
C4—C2—C1	125.99 (10)	C4—C9—C10	110.60 (9)
C4—C2—C3	106.60 (9)	C4—C9—C11	109.86 (9)
N2—C3—C2	106.99 (9)	C4—C9—C12	108.69 (9)
N2—C3—C5	123.33 (10)	C10—C9—C11	109.09 (9)
C2—C3—C5	129.66 (10)	C10—C9—C12	109.18 (10)
N3—C4—C2	107.19 (10)	C11—C9—C12	109.40 (9)
N3—C4—C9	123.09 (10)	C9—C10—H10A	109.5
C2—C4—C9	129.71 (10)	C9—C10—H10B	109.5
C3—C5—C6	110.21 (9)	C9—C10—H10C	109.5
C3—C5—C7	110.86 (9)	H10A—C10—H10B	109.5
C3—C5—C8	108.38 (9)	H10A—C10—H10C	109.5
C6—C5—C7	108.96 (10)	H10B—C10—H10C	109.5
C6—C5—C8	109.37 (10)	C9—C11—H11A	109.5
C7—C5—C8	109.04 (10)	C9—C11—H11B	109.5
C5—C6—H6A	109.5	C9—C11—H11C	109.5
C5—C6—H6B	109.5	H11A—C11—H11B	109.5
C5—C6—H6C	109.5	H11A—C11—H11C	109.5
H6A—C6—H6B	109.5	H11B—C11—H11C	109.5
H6A—C6—H6C	109.5	C9—C12—H12A	109.5
H6B—C6—H6C	109.5	C9—C12—H12B	109.5
C5—C7—H7A	109.5	C9—C12—H12C	109.5
C5—C7—H7B	109.5	H12A—C12—H12B	109.5
C5—C7—H7C	109.5	H12A—C12—H12C	109.5
H7A—C7—H7B	109.5	H12B—C12—H12C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N3ⁱ	0.86 (3)	2.23 (3)	2.9232 (14)	138 (2)
N3—H3···N2ⁱ	0.85 (3)	2.19 (3)	2.9232 (14)	144 (2)

Symmetry code: (i) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N3ⁱ	0.86 (3)	2.23 (3)	2.9232 (14)	138 (2)
N3—H3···N2ⁱ	0.85 (3)	2.19 (3)	2.9232 (14)	144 (2)

Symmetry code: (i) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₉N₃
M_r	205.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	10.5993 (3), 9.7641 (3), 12.4435 (4)
β (°)	109.065 (1)
V (Å³)	1217.17 (6)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.53
Crystal size (mm)	0.15 × 0.10 × 0.09

Data collection
Diffractometer	Bruker D8 Platinum135
Absorption correction	Multi-scan (SADABS; Bruker, 2016)
T_min, T_max	0.211, 0.320
No. of measured, independent and observed [I > 2σ(I)] reflections	11126, 2183, 2037
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.096, 1.05
No. of reflections	2183
No. of parameters	150
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.19

Computer programs: APEX3 (Bruker, 2016), SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a), SHELXL2014 (Sheldrick, 2015b), Mercury (Macrae et al., 2008), OLEX2 (Dolomanov et al., 2009).

Acknowledgements

The authors thank Dr Curtis Moore, Director of X-ray Crystallography Facility at University of California, San Diego, for providing the single-crystal X-ray diffraction data, and the Department of Chemistry at Jacksonville University for supporting the research.

References

Bruker (2016). APEX3, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals 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

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

3,5-Di-tert-butyl-1H-pyrazole-4-carbo­nitrile

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

3,5-Di-tert-butyl-1H-pyrazole-4-carbonitrile