organic compounds
4-Cyano-3,5-bis(phenyl)pyrazole
aDepartment of Chemistry, Jacksonville University, Jacksonville, FL 32211, USA
*Correspondence e-mail: pzhao@ju.edu
There are two independent molecules in the 16H11N3. The molecules are linked by pairs of N—H⋯N hydrogen bonds, forming inversion dimers with an R22 (6) ring motif.
of the title compound, CKeywords: 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 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 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′).
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.
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 .
details are summarized in Table 2Structural data
CCDC reference: 1572144
https://doi.org/10.1107/S2414314617012573/hg4027sup1.cif
contains datablock I. DOI: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
Data collection: APEX3 (Bruker, 2016); cell
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).C16H11N3 | Z = 4 |
Mr = 245.28 | F(000) = 512 |
Triclinic, P1 | Dx = 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 |
Bruker X8 APEX II diffractometer | 5069 independent reflections |
Radiation source: sealed tube, fine-focus | 3178 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
Detector resolution: 7.9 pixels mm-1 | θmax = 26.4°, θmin = 2.3° |
ω and φ scans | h = −12→11 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −11→13 |
Tmin = 0.235, Tmax = 0.260 | l = −16→12 |
25032 measured reflections |
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(Fo2) + (0.0555P)2 + 0.1764P] where P = (Fo2 + 2Fc2)/3 |
5069 reflections | (Δ/σ)max < 0.001 |
343 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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 |
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.
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