4-Cyano-3,5-bis­(phen­yl)pyrazole

Zhao, N.; Adeyemi, A.; Pompilius, A.

doi:10.1107/S2414314617012573

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 9| September 2017| x171257

https://doi.org/10.1107/S2414314617012573

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4-Cyano-3,5-bis(phenyl)pyrazole

Ningfeng Zhao,^a ^* Aanuoluwapo Adeyemi ^a and Arielle Pompilius ^a

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

Edited by P. C. Healy, Griffith University, Australia (Received 30 August 2017; accepted 1 September 2017; online 8 September 2017)

There are two independent molecules in the asymmetric unit of the title compound, C₁₆H₁₁N₃. The molecules are linked by pairs of N—H⋯N hydrogen bonds, forming inversion dimers with an R₂² (6) ring motif.

Keywords: crystal structure; cyano-pyrazole; symmetrical substitutes.

CCDC reference: 1572144

Structure description

The title compound, representing a symmetrically phenyl substituted 4-cyano pyrazole, was prepared as a precursor for the preparation of scorpionate ligands (Trofimenko, 1999 ). There are two molecules in the asymmetric unit. The C—C≡N fragments deviate only slightly from linearity with a bonding angle of 179.4 (2)° (N1—C1—C2) and 178.9 (2)° (N1′—C1′—C2′) (Fig. 1). The dihedral angles between one pyrazole ring (N2/N3/C2–C4) and the mean planes of the two phenyl rings are 21.26° (C5–C10) and 24.31° (C11–C16) in one molecule of the asymmetric unit. In the other molecule, the dihedral angles between the pyrazole ring (N2′/N3′/C2′–C4′) and the mean planes of the two phenyl rings are 19.72° (C5′–C10′) and 34.39° (C11′–C16′).

Figure 1
A view of the asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary radii.

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.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N3ⁱ	0.88	2.13	2.812 (2)	133
N2′—H2′⋯N3′ⁱⁱ	0.88	2.13	2.793 (2)	131
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+2, -y+1, -z+1.

Figure 2
A view along the b axis of the crystal packing of the title compound. The N—H⋯N hydrogen bonds (Table 1

) are shown as dashed lines.

Synthesis and crystallization

Toluene was dried over sodium and benzophenone. All other solvents and reagents were used as received from Alfa Aesar or Fisher Scientific without further purification. The synthesis of 4-cyano-3,5-bisphenyl pyrazole has been reported (Som, 2013 ). The procedure was modified in this work to recrystallize the final product. 0.69 g (17.24 mmol, 60% dispersion in mineral oil) of sodium hydride was added to 100 ml dry toluene. To this solution was added 2.50 g of benzoylacetonitrile (17.24 mmol), resulting in the immediate appearance of bubbles. The mixture was stirred for 18 h before benzoyl chloride (2.43 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 HCl/H₂O (50/50) solution to pH ∼1. A white precipitate appeared immediately and was extracted with three 100 ml portions of ethyl acetate. Removal of the solvent under reduced pressure yielded 2.55 g (10.24 mmol, yield 59.40%) of crude product, which was recrystallized from ethanol to give 2-cyano-1,3-diphenyl-1,3-propanedione (1.38 g, 5.54 mmol, 32.15%). This diketone compound (1.38 g, 5.54 mmol) was then reacted with hydrazine monohydrate (0.28 g, 5.54 mmol) in 100 ml of methanol and stirred overnight. The solvent was removed under reduced pressure to yield the crude product of 4-cyano-3,5-bisphenyl pyrazole as a pale-yellow solid, which was recrystallized from ethanol (1.01 g, 4.65 mmol, 27.00%). Infrared spectroscopy showed characteristic peaks at 3177 cm⁻¹ and 2227 cm⁻¹ for N—H and C≡N stretches respectively. The ¹H NMR (chloroform-d) showed chemical shifts at 8.06 (d, 4H), 7.64 (t, 4H), and 7.54 p.p.m. (t, 2H).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₆H₁₁N₃
M_r	245.28
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	100
a, b, c (Å)	9.6036 (7), 10.4998 (6), 13.4359 (7)
α, β, γ (°)	104.899 (2), 106.704 (2), 90.647 (2)
V (Å³)	1248.70 (13)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.25 × 0.24 × 0.16

Data collection
Diffractometer	Bruker X8 APEX II
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.235, 0.260
No. of measured, independent and observed [I > 2σ(I)] reflections	25032, 5069, 3178
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.122, 1.02
No. of reflections	5069
No. of parameters	343
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.29
Computer programs: APEX3 (Bruker, 2016), SAINT (Bruker, 2016), SHELXL (Sheldrick, 2015 ), OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 1572144

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314617012573/hg4027sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617012573/hg4027Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617012573/hg4027Isup3.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 refine structure: SHELXL (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

4-Cyano-3,5-bis(phenyl)pyrazole top

Crystal data top

C₁₆H₁₁N₃	Z = 4
M_r = 245.28	F(000) = 512
Triclinic, P1	D_x = 1.305 Mg m⁻³
a = 9.6036 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.4998 (6) Å	Cell parameters from 2987 reflections
c = 13.4359 (7) Å	θ = 2.9–26.3°
α = 104.899 (2)°	µ = 0.08 mm⁻¹
β = 106.704 (2)°	T = 100 K
γ = 90.647 (2)°	Block, colourless
V = 1248.70 (13) Å³	0.25 × 0.24 × 0.16 mm

Data collection top

Bruker X8 APEX II diffractometer	5069 independent reflections
Radiation source: sealed tube, fine-focus	3178 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
Detector resolution: 7.9 pixels mm^-1	θ_max = 26.4°, θ_min = 2.3°
ω and φ scans	h = −12→11
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −11→13
T_min = 0.235, T_max = 0.260	l = −16→12
25032 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0555P)² + 0.1764P] where P = (F_o² + 2F_c²)/3
5069 reflections	(Δ/σ)_max < 0.001
343 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

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
N1	−0.02188 (18)	0.73573 (16)	0.25572 (13)	0.0251 (4)
N2	0.37446 (17)	0.51162 (15)	0.39966 (12)	0.0186 (4)
H2	0.433514	0.448492	0.393834	0.022*
N3	0.38722 (16)	0.60550 (15)	0.49310 (12)	0.0179 (4)
C1	0.0762 (2)	0.69081 (18)	0.30236 (15)	0.0176 (4)
C2	0.1967 (2)	0.63420 (17)	0.36031 (14)	0.0162 (4)
C3	0.2628 (2)	0.52451 (17)	0.31689 (14)	0.0155 (4)
C4	0.27925 (19)	0.68260 (17)	0.47057 (14)	0.0154 (4)
C5	0.2349 (2)	0.43615 (18)	0.20816 (14)	0.0164 (4)
C6	0.3463 (2)	0.36427 (19)	0.17986 (15)	0.0213 (5)
H6	0.440196	0.374746	0.231165	0.026*
C7	0.3211 (2)	0.2782 (2)	0.07803 (16)	0.0254 (5)
H7	0.397375	0.229588	0.060013	0.031*
C8	0.1852 (2)	0.2628 (2)	0.00262 (16)	0.0265 (5)
H8	0.167909	0.203569	−0.067200	0.032*
C9	0.0740 (2)	0.3338 (2)	0.02888 (15)	0.0252 (5)
H9	−0.019124	0.324002	−0.023297	0.030*
C10	0.0983 (2)	0.41922 (19)	0.13107 (14)	0.0211 (5)
H10	0.021178	0.466678	0.148755	0.025*
C11	0.2659 (2)	0.79827 (17)	0.55498 (14)	0.0161 (4)
C12	0.1333 (2)	0.85396 (18)	0.55028 (15)	0.0181 (4)
H12	0.048672	0.816321	0.491553	0.022*
C13	0.1247 (2)	0.96388 (18)	0.63099 (15)	0.0204 (4)
H13	0.034133	1.000761	0.627423	0.024*
C14	0.2476 (2)	1.02033 (19)	0.71690 (15)	0.0221 (5)
H14	0.241423	1.095891	0.771824	0.026*
C15	0.3795 (2)	0.96562 (19)	0.72200 (15)	0.0217 (5)
H15	0.463800	1.004018	0.780711	0.026*
C16	0.3891 (2)	0.85577 (18)	0.64240 (14)	0.0184 (4)
H16	0.479864	0.818935	0.646943	0.022*
N1'	0.46981 (18)	0.72545 (15)	0.25682 (12)	0.0225 (4)
N2'	0.87772 (17)	0.59563 (15)	0.49062 (12)	0.0192 (4)
H2'	0.940673	0.601874	0.554283	0.023*
N3'	0.87116 (17)	0.50046 (15)	0.39906 (12)	0.0192 (4)
C1'	0.5726 (2)	0.68557 (17)	0.30272 (14)	0.0163 (4)
C2'	0.69826 (19)	0.63418 (17)	0.35991 (14)	0.0155 (4)
C3'	0.7753 (2)	0.67868 (17)	0.47078 (14)	0.0156 (4)
C4'	0.7634 (2)	0.52153 (17)	0.31792 (14)	0.0154 (4)
C5'	0.7632 (2)	0.79276 (18)	0.55686 (14)	0.0168 (4)
C6'	0.8279 (2)	0.79538 (19)	0.66520 (15)	0.0206 (5)
H6'	0.874686	0.721159	0.682310	0.025*
C7'	0.8244 (2)	0.90496 (19)	0.74751 (16)	0.0245 (5)
H7'	0.868809	0.905714	0.820647	0.029*
C8'	0.7563 (2)	1.01351 (19)	0.72334 (16)	0.0238 (5)
H8'	0.754213	1.088901	0.779799	0.029*
C9'	0.6910 (2)	1.01187 (19)	0.61653 (15)	0.0206 (4)
H9'	0.643333	1.085992	0.600059	0.025*
C10'	0.6948 (2)	0.90301 (18)	0.53375 (15)	0.0181 (4)
H10'	0.650589	0.903232	0.460816	0.022*
C11'	0.73338 (19)	0.43430 (18)	0.20814 (14)	0.0164 (4)
C12'	0.6884 (2)	0.48498 (19)	0.11845 (14)	0.0189 (4)
H12'	0.674383	0.576273	0.128153	0.023*
C13'	0.6642 (2)	0.4018 (2)	0.01540 (15)	0.0230 (5)
H13'	0.634018	0.436559	−0.045343	0.028*
C14'	0.6837 (2)	0.2686 (2)	0.00036 (15)	0.0242 (5)
H14'	0.665821	0.211888	−0.070494	0.029*
C15'	0.7295 (2)	0.2180 (2)	0.08919 (16)	0.0254 (5)
H15'	0.743772	0.126708	0.078976	0.030*
C16'	0.7545 (2)	0.29997 (18)	0.19248 (15)	0.0207 (4)
H16'	0.786021	0.264849	0.252923	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0250 (10)	0.0233 (9)	0.0222 (9)	0.0065 (8)	0.0012 (8)	0.0043 (8)
N2	0.0189 (9)	0.0168 (9)	0.0200 (9)	0.0067 (7)	0.0053 (7)	0.0051 (7)
N3	0.0183 (9)	0.0166 (9)	0.0187 (9)	0.0044 (7)	0.0059 (7)	0.0042 (7)
C1	0.0193 (11)	0.0155 (10)	0.0166 (10)	0.0027 (9)	0.0050 (9)	0.0020 (8)
C2	0.0159 (10)	0.0156 (10)	0.0180 (10)	0.0015 (8)	0.0048 (8)	0.0066 (8)
C3	0.0132 (10)	0.0169 (10)	0.0170 (10)	0.0016 (8)	0.0028 (8)	0.0075 (8)
C4	0.0135 (10)	0.0153 (10)	0.0182 (10)	0.0012 (8)	0.0037 (8)	0.0074 (8)
C5	0.0179 (10)	0.0169 (10)	0.0159 (10)	0.0016 (8)	0.0057 (8)	0.0066 (8)
C6	0.0194 (11)	0.0243 (11)	0.0217 (11)	0.0035 (9)	0.0072 (9)	0.0079 (9)
C7	0.0291 (12)	0.0269 (12)	0.0234 (11)	0.0085 (10)	0.0133 (10)	0.0058 (9)
C8	0.0326 (13)	0.0278 (12)	0.0177 (11)	0.0028 (10)	0.0084 (10)	0.0028 (9)
C9	0.0240 (12)	0.0313 (12)	0.0171 (11)	0.0037 (9)	0.0023 (9)	0.0054 (9)
C10	0.0203 (11)	0.0234 (11)	0.0202 (11)	0.0047 (9)	0.0061 (9)	0.0065 (9)
C11	0.0193 (11)	0.0150 (10)	0.0161 (10)	0.0030 (8)	0.0062 (8)	0.0069 (8)
C12	0.0197 (11)	0.0181 (10)	0.0168 (10)	0.0016 (8)	0.0053 (8)	0.0055 (8)
C13	0.0205 (11)	0.0210 (11)	0.0244 (11)	0.0062 (9)	0.0110 (9)	0.0094 (9)
C14	0.0291 (12)	0.0179 (10)	0.0204 (11)	0.0025 (9)	0.0118 (9)	0.0026 (9)
C15	0.0223 (11)	0.0215 (11)	0.0192 (11)	−0.0011 (9)	0.0043 (9)	0.0041 (9)
C16	0.0182 (11)	0.0186 (10)	0.0198 (10)	0.0036 (8)	0.0054 (9)	0.0077 (9)
N1'	0.0234 (10)	0.0217 (9)	0.0192 (9)	0.0034 (8)	0.0023 (8)	0.0043 (7)
N2'	0.0192 (9)	0.0195 (9)	0.0161 (9)	0.0021 (7)	0.0005 (7)	0.0052 (7)
N3'	0.0202 (9)	0.0202 (9)	0.0149 (9)	0.0000 (7)	0.0022 (7)	0.0046 (7)
C1'	0.0190 (11)	0.0151 (10)	0.0145 (10)	−0.0002 (8)	0.0052 (8)	0.0035 (8)
C2'	0.0136 (10)	0.0167 (10)	0.0156 (10)	0.0007 (8)	0.0028 (8)	0.0057 (8)
C3'	0.0149 (10)	0.0150 (10)	0.0183 (10)	0.0028 (8)	0.0046 (8)	0.0072 (8)
C4'	0.0146 (10)	0.0161 (10)	0.0166 (10)	0.0002 (8)	0.0045 (8)	0.0065 (8)
C5'	0.0152 (10)	0.0178 (10)	0.0180 (10)	−0.0004 (8)	0.0061 (8)	0.0047 (8)
C6'	0.0212 (11)	0.0222 (11)	0.0201 (11)	0.0010 (9)	0.0056 (9)	0.0093 (9)
C7'	0.0274 (12)	0.0279 (12)	0.0171 (10)	−0.0013 (9)	0.0059 (9)	0.0054 (9)
C8'	0.0255 (12)	0.0213 (11)	0.0239 (11)	−0.0027 (9)	0.0125 (9)	−0.0006 (9)
C9'	0.0194 (11)	0.0180 (10)	0.0264 (11)	0.0030 (8)	0.0091 (9)	0.0072 (9)
C10'	0.0173 (10)	0.0196 (10)	0.0183 (10)	0.0023 (8)	0.0061 (8)	0.0061 (9)
C11'	0.0116 (10)	0.0200 (10)	0.0170 (10)	0.0021 (8)	0.0041 (8)	0.0040 (8)
C12'	0.0178 (11)	0.0202 (10)	0.0180 (10)	0.0038 (8)	0.0036 (8)	0.0056 (9)
C13'	0.0209 (11)	0.0308 (12)	0.0182 (10)	0.0054 (9)	0.0057 (9)	0.0085 (9)
C14'	0.0236 (12)	0.0272 (12)	0.0191 (11)	0.0039 (9)	0.0071 (9)	0.0006 (9)
C15'	0.0292 (12)	0.0205 (11)	0.0266 (12)	0.0056 (9)	0.0104 (10)	0.0046 (9)
C16'	0.0226 (11)	0.0228 (11)	0.0175 (10)	0.0024 (9)	0.0056 (9)	0.0072 (9)

Geometric parameters (Å, º) top

N1—C1	1.151 (2)	N1'—C1'	1.150 (2)
N2—H2	0.8800	N2'—H2'	0.8800
N2—N3	1.355 (2)	N2'—N3'	1.356 (2)
N2—C3	1.342 (2)	N2'—C3'	1.337 (2)
N3—C4	1.337 (2)	N3'—C4'	1.338 (2)
C1—C2	1.426 (3)	C1'—C2'	1.426 (3)
C2—C3	1.398 (2)	C2'—C3'	1.409 (2)
C2—C4	1.418 (2)	C2'—C4'	1.409 (2)
C3—C5	1.463 (3)	C3'—C5'	1.468 (3)
C4—C11	1.468 (3)	C4'—C11'	1.467 (3)
C5—C6	1.401 (3)	C5'—C6'	1.402 (2)
C5—C10	1.394 (3)	C5'—C10'	1.398 (2)
C6—H6	0.9500	C6'—H6'	0.9500
C6—C7	1.384 (3)	C6'—C7'	1.384 (3)
C7—H7	0.9500	C7'—H7'	0.9500
C7—C8	1.381 (3)	C7'—C8'	1.385 (3)
C8—H8	0.9500	C8'—H8'	0.9500
C8—C9	1.385 (3)	C8'—C9'	1.387 (3)
C9—H9	0.9500	C9'—H9'	0.9500
C9—C10	1.386 (3)	C9'—C10'	1.384 (3)
C10—H10	0.9500	C10'—H10'	0.9500
C11—C12	1.400 (3)	C11'—C12'	1.399 (2)
C11—C16	1.401 (3)	C11'—C16'	1.397 (3)
C12—H12	0.9500	C12'—H12'	0.9500
C12—C13	1.387 (3)	C12'—C13'	1.386 (3)
C13—H13	0.9500	C13'—H13'	0.9500
C13—C14	1.387 (3)	C13'—C14'	1.384 (3)
C14—H14	0.9500	C14'—H14'	0.9500
C14—C15	1.388 (3)	C14'—C15'	1.389 (3)
C15—H15	0.9500	C15'—H15'	0.9500
C15—C16	1.381 (3)	C15'—C16'	1.383 (3)
C16—H16	0.9500	C16'—H16'	0.9500

N3—N2—H2	123.4	N3'—N2'—H2'	124.7
C3—N2—H2	123.4	C3'—N2'—H2'	124.7
C3—N2—N3	113.27 (15)	C3'—N2'—N3'	110.59 (15)
C4—N3—N2	106.08 (14)	C4'—N3'—N2'	108.59 (15)
N1—C1—C2	179.40 (19)	N1'—C1'—C2'	178.85 (18)
C3—C2—C1	126.21 (16)	C3'—C2'—C1'	127.30 (17)
C3—C2—C4	106.48 (15)	C4'—C2'—C1'	126.42 (16)
C4—C2—C1	127.18 (17)	C4'—C2'—C3'	106.12 (15)
N2—C3—C2	105.10 (16)	N2'—C3'—C2'	106.76 (16)
N2—C3—C5	121.48 (17)	N2'—C3'—C5'	120.83 (16)
C2—C3—C5	133.38 (17)	C2'—C3'—C5'	132.37 (16)
N3—C4—C2	109.06 (16)	N3'—C4'—C2'	107.95 (16)
N3—C4—C11	119.72 (16)	N3'—C4'—C11'	120.35 (17)
C2—C4—C11	131.19 (16)	C2'—C4'—C11'	131.69 (16)
C6—C5—C3	119.99 (17)	C6'—C5'—C3'	119.77 (16)
C10—C5—C3	121.67 (17)	C10'—C5'—C3'	121.56 (16)
C10—C5—C6	118.34 (17)	C10'—C5'—C6'	118.58 (17)
C5—C6—H6	119.6	C5'—C6'—H6'	119.7
C7—C6—C5	120.81 (18)	C7'—C6'—C5'	120.69 (17)
C7—C6—H6	119.6	C7'—C6'—H6'	119.7
C6—C7—H7	120.0	C6'—C7'—H7'	120.0
C8—C7—C6	120.07 (19)	C6'—C7'—C8'	120.06 (18)
C8—C7—H7	120.0	C8'—C7'—H7'	120.0
C7—C8—H8	120.0	C7'—C8'—H8'	120.1
C7—C8—C9	119.94 (19)	C7'—C8'—C9'	119.83 (18)
C9—C8—H8	120.0	C9'—C8'—H8'	120.1
C8—C9—H9	119.9	C8'—C9'—H9'	119.8
C8—C9—C10	120.19 (19)	C10'—C9'—C8'	120.47 (18)
C10—C9—H9	119.9	C10'—C9'—H9'	119.8
C5—C10—H10	119.7	C5'—C10'—H10'	119.8
C9—C10—C5	120.66 (19)	C9'—C10'—C5'	120.36 (17)
C9—C10—H10	119.7	C9'—C10'—H10'	119.8
C12—C11—C4	121.76 (17)	C12'—C11'—C4'	120.66 (16)
C12—C11—C16	118.72 (17)	C16'—C11'—C4'	120.00 (15)
C16—C11—C4	119.52 (17)	C16'—C11'—C12'	119.30 (17)
C11—C12—H12	119.9	C11'—C12'—H12'	120.0
C13—C12—C11	120.28 (18)	C13'—C12'—C11'	119.92 (17)
C13—C12—H12	119.9	C13'—C12'—H12'	120.0
C12—C13—H13	119.8	C12'—C13'—H13'	119.8
C12—C13—C14	120.48 (18)	C14'—C13'—C12'	120.49 (17)
C14—C13—H13	119.8	C14'—C13'—H13'	119.8
C13—C14—H14	120.2	C13'—C14'—H14'	120.1
C13—C14—C15	119.52 (19)	C13'—C14'—C15'	119.80 (18)
C15—C14—H14	120.2	C15'—C14'—H14'	120.1
C14—C15—H15	119.7	C14'—C15'—H15'	119.9
C16—C15—C14	120.51 (19)	C16'—C15'—C14'	120.29 (18)
C16—C15—H15	119.7	C16'—C15'—H15'	119.9
C11—C16—H16	119.8	C11'—C16'—H16'	119.9
C15—C16—C11	120.49 (18)	C15'—C16'—C11'	120.18 (17)
C15—C16—H16	119.8	C15'—C16'—H16'	119.9

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N3ⁱ	0.88	2.13	2.812 (2)	133
N2′—H2′···N3′ⁱⁱ	0.88	2.13	2.793 (2)	131

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

Acknowledgements

The authors thank Dr Curtis Moore, Director of the 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

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