organic compounds
5-Methyl-4-(5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-phenyl-1H-pyrazol-3(2H)-one
aDepartment of Chemistry & Biochemistry, Abilene Christian University, Abilene, Texas 79699-8132, USA
*Correspondence e-mail: powellg@acu.edu
The title compound, C20H18N4O2, known as bispyrazolone, was crystallized from dimethyl sulfoxide. The structure has orthorhombic (Pbca) symmetry at 150 K, and displays both intra- and intermolecular hydrogen bonding through C—H⋯O and N—H⋯O contacts, respectively. None of the phenyl and pyrazolone rings in the molecule are coplanar. The dihedral angle between the pyrazolone rings is 66.18 (5)°.
Keywords: crystal structure; pyrazolone rings; hydrogen bonding.
CCDC reference: 1949067
Structure description
Pyrazolones have been studied as antipyretics and analgesics (Brune, 1997; Badawey & El–Ashmawey, 1998; Gürsoy et al., 2000), as anxiolytics (Geronikaki et al., 2004), and as antihyperglycemic agents (Kees et al., 1996). These compound types have also been found to have antioxidant and neuroprotective activities, and have been used to treat amyotrophic lateral sclerosis (ALS) and ischemia (Watanabe et al., 2004; Yoshida et al., 2006; Yuan et al., 2008). Pyrazolones have also been looked at as potential HIV-1 integrase inhibitors (Hadi, et al., 2010). In addition to the multitude of possibilities in medicinal chemistry, pyrazolone research has led to prospective antimicrobial compounds (Chande et al., 2007) and corrosion inhibitors (Elmorsi & Hassanein, 1999). The title compound, bispyrazolone, is primarily used as part of a pyridine-pyrazolone reagent for the detection of amine compounds. This method can quantify levels of cyanide (Epstein, 1947), ammonia and cyanate (Kruse & Mellon, 1952), and urea (Sharma et al., 2013). It may also be used to determine the percentage of nitrogen in steel samples (Lear & Mellon, 1957). Bispyrazolone and similar derivatives have also been examined as color developers (Bavley, 1946) and as lubricating oil thickeners (McGrath and Pellegrini, 1961) for high-temperature greases.
In the ). The dihedral angle between the two pyrazolone rings is 66.18 (5)°, while that between the phenyl rings is 39.44 (6)°. The ring systems in the halves of the molecules have significantly different degrees of rotation with respect to one another. The dihedral angle between the C9–C14 phenyl ring and the N1/N2/C1–C3 pyrazolone ring is 34.29 (6)° while that between the C15–C20 phenyl ring and the N3/N4/C5–C7 pyrazolone ring is 13.75 (7)°. The latter is a consequence of intramolecular C—H⋯O hydrogen bonding between the C20—H20 group on the phenyl ring and the O2 atom of the pyrazolone ring (Table 1, Fig. 2).
of the title compound, the molecules are non-planar (Fig. 1In the crystal, the molecules pack in a manner that maximizes intermolecular hydrogen bonding. Both oxygen atoms and both N—H groups of each bispyrazolone molecule are involved in forming four hydrogen bonds with three neighboring molecules (Table 1, Fig. 2). The intermolecular hydrogen bond axes lie approximately in the bc plane of the Thus hydrogen-bonded sheets of the molecules stack perpendicular to the a axis (Fig. 3).
Synthesis and crystallization
A sample of the title compound was used as received from Sigma–Aldrich, and dissolved in hot dimethylsulfoxide. Colorless crystals were obtained by slow cooling of this solution to 298 K.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
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Structural data
CCDC reference: 1949067
https://doi.org/10.1107/S2414314620001212/wm4125sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314620001212/wm4125Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314620001212/wm4125Isup3.cml
Data collection: CrysAlis PRO (Rigaku OD, 2019); cell
CrysAlis PRO (Rigaku OD, 2019); data reduction: CrysAlis PRO (Rigaku OD, 2019); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).C20H18N4O2 | Dx = 1.349 Mg m−3 |
Mr = 346.38 | Cu Kα radiation, λ = 1.54184 Å |
Orthorhombic, Pbca | Cell parameters from 9599 reflections |
a = 8.7438 (1) Å | θ = 4.7–72.3° |
b = 18.7561 (2) Å | µ = 0.73 mm−1 |
c = 20.8005 (2) Å | T = 150 K |
V = 3411.27 (6) Å3 | Plate, clear colourless |
Z = 8 | 0.27 × 0.21 × 0.03 mm |
F(000) = 1456 |
Rigaku Oxford Diffraction SuperNova, Cu, AtlasS2 CCD diffractometer | 3336 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source | 3020 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.028 |
Detector resolution: 5.2387 pixels mm-1 | θmax = 72.6°, θmin = 4.3° |
ω scans | h = −7→10 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2019) | k = −22→23 |
Tmin = 0.874, Tmax = 1.000 | l = −25→24 |
16964 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | All H-atom parameters refined |
wR(F2) = 0.113 | w = 1/[σ2(Fo2) + (0.0692P)2 + 1.0751P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
3336 reflections | Δρmax = 0.26 e Å−3 |
307 parameters | Δρmin = −0.25 e Å−3 |
0 restraints |
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. |
Refinement. The H atoms bound to N2 and N4 were located in a difference map and refined. All hydrogen atoms were located in a difference map and were refined isotropically without constraints. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.17850 (10) | 0.59409 (5) | 0.52406 (4) | 0.0228 (2) | |
O2 | 0.41464 (11) | 0.62429 (5) | 0.38211 (4) | 0.0254 (2) | |
N1 | 0.33303 (11) | 0.51616 (5) | 0.58208 (5) | 0.0197 (2) | |
N2 | 0.48738 (12) | 0.51224 (6) | 0.59817 (5) | 0.0203 (2) | |
H2 | 0.525 (2) | 0.4688 (11) | 0.6043 (9) | 0.040 (5)* | |
N3 | 0.49474 (13) | 0.74084 (6) | 0.40463 (5) | 0.0228 (2) | |
N4 | 0.53811 (15) | 0.77703 (6) | 0.45972 (6) | 0.0283 (3) | |
H4 | 0.587 (2) | 0.8209 (12) | 0.4598 (9) | 0.043 (5)* | |
C1 | 0.30864 (14) | 0.57394 (6) | 0.54173 (6) | 0.0189 (3) | |
C2 | 0.45779 (14) | 0.60260 (6) | 0.52877 (6) | 0.0200 (3) | |
C3 | 0.56144 (15) | 0.56250 (6) | 0.56271 (6) | 0.0205 (3) | |
C4 | 0.73088 (16) | 0.56807 (8) | 0.56622 (7) | 0.0280 (3) | |
H4A | 0.760 (2) | 0.5841 (11) | 0.6082 (10) | 0.047 (5)* | |
H4B | 0.769 (2) | 0.6027 (12) | 0.5330 (10) | 0.048 (5)* | |
H4C | 0.781 (2) | 0.5205 (13) | 0.5591 (11) | 0.057 (6)* | |
C5 | 0.46008 (14) | 0.67053 (6) | 0.42150 (6) | 0.0206 (3) | |
C6 | 0.48650 (14) | 0.66557 (6) | 0.48898 (6) | 0.0210 (3) | |
C7 | 0.53634 (16) | 0.73124 (7) | 0.50942 (7) | 0.0252 (3) | |
C8 | 0.5806 (2) | 0.75544 (8) | 0.57491 (7) | 0.0378 (4) | |
H8A | 0.615 (3) | 0.7180 (16) | 0.6015 (14) | 0.088 (9)* | |
H8B | 0.657 (3) | 0.7932 (13) | 0.5731 (11) | 0.060 (6)* | |
H8C | 0.490 (3) | 0.7748 (16) | 0.5982 (14) | 0.086 (9)* | |
C9 | 0.22459 (14) | 0.47963 (6) | 0.62063 (6) | 0.0203 (3) | |
C10 | 0.26090 (16) | 0.46291 (7) | 0.68395 (7) | 0.0249 (3) | |
H10 | 0.3582 (19) | 0.4766 (9) | 0.7016 (8) | 0.028 (4)* | |
C11 | 0.15554 (16) | 0.42644 (7) | 0.72142 (7) | 0.0282 (3) | |
H11 | 0.1800 (19) | 0.4165 (9) | 0.7650 (9) | 0.030 (4)* | |
C12 | 0.01470 (16) | 0.40714 (7) | 0.69603 (7) | 0.0280 (3) | |
H12 | −0.060 (2) | 0.3814 (9) | 0.7228 (9) | 0.033 (4)* | |
C13 | −0.02218 (15) | 0.42573 (7) | 0.63351 (7) | 0.0264 (3) | |
H13 | −0.122 (2) | 0.4129 (9) | 0.6151 (8) | 0.031 (4)* | |
C14 | 0.08272 (15) | 0.46155 (7) | 0.59499 (7) | 0.0234 (3) | |
H14 | 0.0610 (18) | 0.4727 (9) | 0.5502 (8) | 0.025 (4)* | |
C15 | 0.47280 (15) | 0.77740 (7) | 0.34550 (6) | 0.0232 (3) | |
C16 | 0.52997 (19) | 0.84583 (8) | 0.33728 (8) | 0.0349 (4) | |
H16 | 0.585 (2) | 0.8683 (12) | 0.3736 (11) | 0.056 (6)* | |
C17 | 0.5073 (2) | 0.88090 (8) | 0.27926 (8) | 0.0388 (4) | |
H17 | 0.552 (2) | 0.9301 (11) | 0.2736 (10) | 0.046 (5)* | |
C18 | 0.4295 (2) | 0.84888 (8) | 0.22973 (7) | 0.0368 (4) | |
H18 | 0.417 (2) | 0.8738 (10) | 0.1885 (9) | 0.040 (5)* | |
C19 | 0.3694 (2) | 0.78142 (9) | 0.23859 (8) | 0.0440 (4) | |
H19 | 0.313 (2) | 0.7578 (12) | 0.2045 (11) | 0.054 (6)* | |
C20 | 0.3906 (2) | 0.74557 (8) | 0.29632 (7) | 0.0367 (4) | |
H20 | 0.352 (2) | 0.6986 (12) | 0.3029 (10) | 0.051 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0240 (5) | 0.0187 (4) | 0.0256 (5) | 0.0027 (3) | −0.0025 (4) | 0.0029 (3) |
O2 | 0.0357 (5) | 0.0157 (4) | 0.0249 (5) | −0.0017 (3) | −0.0066 (4) | 0.0006 (3) |
N1 | 0.0195 (5) | 0.0171 (5) | 0.0225 (5) | 0.0002 (4) | −0.0011 (4) | 0.0039 (4) |
N2 | 0.0209 (5) | 0.0164 (5) | 0.0236 (6) | 0.0011 (4) | −0.0016 (4) | 0.0029 (4) |
N3 | 0.0324 (6) | 0.0162 (5) | 0.0197 (5) | −0.0033 (4) | −0.0008 (4) | 0.0012 (4) |
N4 | 0.0449 (7) | 0.0185 (5) | 0.0213 (6) | −0.0102 (5) | −0.0016 (5) | 0.0012 (4) |
C1 | 0.0256 (6) | 0.0143 (5) | 0.0167 (6) | 0.0014 (4) | −0.0002 (5) | 0.0000 (4) |
C2 | 0.0255 (6) | 0.0156 (6) | 0.0190 (6) | −0.0012 (4) | −0.0001 (5) | 0.0005 (5) |
C3 | 0.0248 (6) | 0.0167 (5) | 0.0200 (6) | −0.0008 (5) | 0.0007 (5) | −0.0007 (5) |
C4 | 0.0241 (7) | 0.0275 (7) | 0.0324 (8) | −0.0017 (5) | −0.0014 (6) | 0.0024 (6) |
C5 | 0.0231 (6) | 0.0147 (5) | 0.0241 (6) | 0.0002 (4) | 0.0000 (5) | 0.0022 (5) |
C6 | 0.0246 (6) | 0.0166 (6) | 0.0219 (6) | −0.0014 (5) | 0.0006 (5) | 0.0018 (5) |
C7 | 0.0339 (7) | 0.0193 (6) | 0.0224 (7) | −0.0040 (5) | 0.0005 (5) | 0.0014 (5) |
C8 | 0.0647 (11) | 0.0249 (7) | 0.0238 (7) | −0.0129 (7) | −0.0052 (7) | −0.0002 (6) |
C9 | 0.0236 (6) | 0.0141 (5) | 0.0233 (6) | 0.0005 (4) | 0.0021 (5) | 0.0019 (4) |
C10 | 0.0266 (6) | 0.0227 (6) | 0.0255 (7) | −0.0013 (5) | −0.0012 (5) | 0.0033 (5) |
C11 | 0.0332 (7) | 0.0262 (6) | 0.0253 (7) | 0.0020 (5) | 0.0031 (6) | 0.0079 (5) |
C12 | 0.0275 (7) | 0.0216 (6) | 0.0350 (8) | 0.0008 (5) | 0.0096 (6) | 0.0051 (5) |
C13 | 0.0229 (6) | 0.0206 (6) | 0.0357 (8) | −0.0004 (5) | 0.0013 (6) | 0.0010 (5) |
C14 | 0.0245 (6) | 0.0198 (6) | 0.0258 (7) | 0.0009 (5) | −0.0009 (5) | 0.0012 (5) |
C15 | 0.0285 (6) | 0.0192 (6) | 0.0218 (6) | 0.0020 (5) | 0.0035 (5) | 0.0035 (5) |
C16 | 0.0443 (8) | 0.0274 (7) | 0.0330 (8) | −0.0110 (6) | −0.0079 (7) | 0.0083 (6) |
C17 | 0.0509 (9) | 0.0276 (7) | 0.0381 (9) | −0.0095 (6) | −0.0046 (7) | 0.0127 (6) |
C18 | 0.0549 (9) | 0.0295 (7) | 0.0261 (7) | 0.0019 (7) | −0.0006 (7) | 0.0088 (6) |
C19 | 0.0753 (12) | 0.0302 (7) | 0.0265 (8) | −0.0055 (8) | −0.0128 (8) | 0.0028 (6) |
C20 | 0.0616 (10) | 0.0210 (7) | 0.0274 (8) | −0.0076 (7) | −0.0076 (7) | 0.0029 (6) |
O1—C1 | 1.2540 (15) | C8—H8C | 1.00 (3) |
O2—C5 | 1.2577 (16) | C9—C10 | 1.3908 (18) |
N1—N2 | 1.3924 (15) | C9—C14 | 1.3922 (18) |
N1—C1 | 1.3873 (15) | C10—H10 | 0.962 (17) |
N1—C9 | 1.4182 (16) | C10—C11 | 1.3870 (19) |
N2—H2 | 0.89 (2) | C11—H11 | 0.950 (18) |
N2—C3 | 1.3608 (16) | C11—C12 | 1.388 (2) |
N3—N4 | 1.3848 (15) | C12—H12 | 0.986 (18) |
N3—C5 | 1.3979 (15) | C12—C13 | 1.384 (2) |
N3—C15 | 1.4211 (16) | C13—H13 | 0.982 (18) |
N4—H4 | 0.93 (2) | C13—C14 | 1.3908 (19) |
N4—C7 | 1.3442 (17) | C14—H14 | 0.973 (17) |
C1—C2 | 1.4361 (17) | C15—C16 | 1.3880 (19) |
C2—C3 | 1.3732 (18) | C15—C20 | 1.385 (2) |
C2—C6 | 1.4638 (17) | C16—H16 | 0.99 (2) |
C3—C4 | 1.4870 (18) | C16—C17 | 1.389 (2) |
C4—H4A | 0.96 (2) | C17—H17 | 1.01 (2) |
C4—H4B | 1.01 (2) | C17—C18 | 1.373 (2) |
C4—H4C | 1.00 (2) | C18—H18 | 0.984 (19) |
C5—C6 | 1.4255 (18) | C18—C19 | 1.382 (2) |
C6—C7 | 1.3739 (18) | C19—H19 | 0.97 (2) |
C7—C8 | 1.487 (2) | C19—C20 | 1.389 (2) |
C8—H8A | 0.94 (3) | C20—H20 | 0.95 (2) |
C8—H8B | 0.98 (2) | ||
N2—N1—C9 | 119.13 (10) | H8A—C8—H8B | 110 (2) |
C1—N1—N2 | 109.61 (10) | H8A—C8—H8C | 104 (2) |
C1—N1—C9 | 128.07 (10) | H8B—C8—H8C | 108 (2) |
N1—N2—H2 | 116.1 (12) | C10—C9—N1 | 119.46 (11) |
C3—N2—N1 | 107.13 (10) | C10—C9—C14 | 120.74 (12) |
C3—N2—H2 | 122.7 (12) | C14—C9—N1 | 119.80 (12) |
N4—N3—C5 | 108.30 (10) | C9—C10—H10 | 120.3 (10) |
N4—N3—C15 | 121.11 (10) | C11—C10—C9 | 119.46 (13) |
C5—N3—C15 | 130.03 (11) | C11—C10—H10 | 120.3 (10) |
N3—N4—H4 | 124.2 (12) | C10—C11—H11 | 118.9 (10) |
C7—N4—N3 | 108.67 (11) | C10—C11—C12 | 120.27 (13) |
C7—N4—H4 | 124.8 (12) | C12—C11—H11 | 120.8 (10) |
O1—C1—N1 | 123.52 (11) | C11—C12—H12 | 120.1 (10) |
O1—C1—C2 | 131.01 (11) | C13—C12—C11 | 119.90 (13) |
N1—C1—C2 | 105.45 (10) | C13—C12—H12 | 120.0 (10) |
C1—C2—C6 | 124.33 (11) | C12—C13—H13 | 120.7 (10) |
C3—C2—C1 | 107.32 (11) | C12—C13—C14 | 120.61 (13) |
C3—C2—C6 | 128.27 (12) | C14—C13—H13 | 118.7 (10) |
N2—C3—C2 | 110.12 (11) | C9—C14—H14 | 119.2 (10) |
N2—C3—C4 | 119.75 (11) | C13—C14—C9 | 118.99 (12) |
C2—C3—C4 | 130.11 (12) | C13—C14—H14 | 121.7 (10) |
C3—C4—H4A | 109.2 (12) | C16—C15—N3 | 120.27 (13) |
C3—C4—H4B | 110.2 (12) | C20—C15—N3 | 120.08 (12) |
C3—C4—H4C | 111.4 (13) | C20—C15—C16 | 119.63 (13) |
H4A—C4—H4B | 109.6 (17) | C15—C16—H16 | 118.3 (13) |
H4A—C4—H4C | 107.4 (18) | C15—C16—C17 | 119.58 (14) |
H4B—C4—H4C | 109.1 (17) | C17—C16—H16 | 122.1 (13) |
O2—C5—N3 | 123.75 (12) | C16—C17—H17 | 118.7 (11) |
O2—C5—C6 | 130.37 (11) | C18—C17—C16 | 121.05 (14) |
N3—C5—C6 | 105.88 (10) | C18—C17—H17 | 120.2 (11) |
C5—C6—C2 | 125.56 (11) | C17—C18—H18 | 120.2 (11) |
C7—C6—C2 | 127.07 (12) | C17—C18—C19 | 119.25 (14) |
C7—C6—C5 | 107.31 (11) | C19—C18—H18 | 120.6 (11) |
N4—C7—C6 | 109.78 (12) | C18—C19—H19 | 120.9 (13) |
N4—C7—C8 | 120.43 (12) | C18—C19—C20 | 120.51 (15) |
C6—C7—C8 | 129.77 (12) | C20—C19—H19 | 118.6 (13) |
C7—C8—H8A | 113.1 (18) | C15—C20—C19 | 119.94 (14) |
C7—C8—H8B | 111.4 (14) | C15—C20—H20 | 118.5 (13) |
C7—C8—H8C | 110.3 (16) | C19—C20—H20 | 121.5 (13) |
O1—C1—C2—C3 | 176.71 (13) | C1—C2—C6—C7 | 110.02 (16) |
O1—C1—C2—C6 | −0.3 (2) | C2—C6—C7—N4 | −175.33 (13) |
O2—C5—C6—C2 | −3.0 (2) | C2—C6—C7—C8 | 3.0 (3) |
O2—C5—C6—C7 | 179.71 (14) | C3—C2—C6—C5 | 116.89 (15) |
N1—N2—C3—C2 | 5.32 (14) | C3—C2—C6—C7 | −66.4 (2) |
N1—N2—C3—C4 | −175.97 (11) | C5—N3—N4—C7 | 1.98 (15) |
N1—C1—C2—C3 | −1.56 (14) | C5—N3—C15—C16 | −173.56 (14) |
N1—C1—C2—C6 | −178.61 (11) | C5—N3—C15—C20 | 8.1 (2) |
N1—C9—C10—C11 | −179.24 (12) | C5—C6—C7—N4 | 1.88 (16) |
N1—C9—C14—C13 | 180.00 (11) | C5—C6—C7—C8 | −179.78 (16) |
N2—N1—C1—O1 | −173.60 (11) | C6—C2—C3—N2 | 174.55 (12) |
N2—N1—C1—C2 | 4.83 (13) | C6—C2—C3—C4 | −4.0 (2) |
N2—N1—C9—C10 | 23.01 (16) | C9—N1—N2—C3 | −167.76 (11) |
N2—N1—C9—C14 | −157.62 (11) | C9—N1—C1—O1 | −14.3 (2) |
N3—N4—C7—C6 | −2.41 (16) | C9—N1—C1—C2 | 164.12 (12) |
N3—N4—C7—C8 | 179.07 (14) | C9—C10—C11—C12 | −0.3 (2) |
N3—C5—C6—C2 | 176.64 (12) | C10—C9—C14—C13 | −0.64 (19) |
N3—C5—C6—C7 | −0.62 (14) | C10—C11—C12—C13 | −1.4 (2) |
N3—C15—C16—C17 | −179.85 (14) | C11—C12—C13—C14 | 2.2 (2) |
N3—C15—C20—C19 | −179.98 (15) | C12—C13—C14—C9 | −1.17 (19) |
N4—N3—C5—O2 | 178.89 (12) | C14—C9—C10—C11 | 1.40 (19) |
N4—N3—C5—C6 | −0.81 (14) | C15—N3—N4—C7 | 174.20 (12) |
N4—N3—C15—C16 | 16.11 (19) | C15—N3—C5—O2 | 7.6 (2) |
N4—N3—C15—C20 | −162.19 (14) | C15—N3—C5—C6 | −172.10 (12) |
C1—N1—N2—C3 | −6.34 (13) | C15—C16—C17—C18 | −0.2 (3) |
C1—N1—C9—C10 | −134.57 (13) | C16—C15—C20—C19 | 1.7 (3) |
C1—N1—C9—C14 | 44.80 (18) | C16—C17—C18—C19 | 1.8 (3) |
C1—C2—C3—N2 | −2.35 (14) | C17—C18—C19—C20 | −1.6 (3) |
C1—C2—C3—C4 | 179.11 (13) | C18—C19—C20—C15 | −0.1 (3) |
C1—C2—C6—C5 | −66.70 (18) | C20—C15—C16—C17 | −1.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O2i | 0.89 (2) | 1.85 (2) | 2.7313 (14) | 175.1 (18) |
N4—H4···O1ii | 0.93 (2) | 1.81 (2) | 2.7321 (15) | 169.3 (18) |
C20—H20···O2 | 0.95 (2) | 2.23 (2) | 2.8988 (17) | 126.5 (16) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1/2, −y+3/2, −z+1. |
Funding information
Funding for this research was provided by: The Welch Foundation (grant No. R-0021).
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