research communications
Ethyl 2-(4-benzyl-3-methyl-6-oxo-1,6-dihydropyridazin-1-yl)acetate:
and Hirshfeld surface analysisaLaboratory of Medicinal Chemistry, Drug Sciences Research Center, Faculty of Medicine and Pharmacy, Mohammed V University, Rabat, Morocco, bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, cDepartment of Physics, Bhavan's Sheth R. A. College of Science, Ahmedabad, Gujarat 380001, India, and dResearch Centre for Crystalline Materials, School of Science and Technology, Sunway University, 47500 Bandar Sunway, Selangor Darul Ehsan, Malaysia
*Correspondence e-mail: edwardt@sunway.edu.my
The title compound, C16H18N2O3, is constructed about a central oxopyridazinyl ring (r.m.s. deviation = 0.0047 Å), which is connected to an ethylacetate group at the N atom closest to the carbonyl group, and benzyl and methyl groups second furthest and furthest from the carbonyl group, respectively. An approximately orthogonal relationship exists between the oxopyridazinyl ring and the best plane through the ethylacetate group [dihedral angle = 77.48 (3)°]; the latter lies to one side of the central plane [the Nr—Nr—Cm—Cc (r = ring, m = methylene, c = carbonyl) torsion angle being 104.34 (9)°]. In the crystal, both H atoms of the N-bound methylene group form methylene-C—H⋯O(ring carbonyl) or N(pyridazinyl) interactions, resulting in the formation of a supramolecular tape along the a-axis direction. The tapes are assembled into a three-dimensional architecture by methyl- and phenyl-C—H⋯O(ring carbonyl) and phenyl-C—H⋯O(ester carbonyl) interactions. The analysis of the calculated Hirshfeld surface indicates the dominance of H⋯H contacts to the overall surface (i.e. 52.2%). Reflecting other identified points of contact between molecules noted above, O⋯H/H⋯O (23.3%), C⋯H/H⋯C (14.7%) and N⋯H/H⋯N (6.6%) contacts also make significant contributions to the surface.
Keywords: crystal structure; oxopyridazinyl; ester; Hirshfeld surface analysis.
CCDC reference: 1897511
1. Chemical context
Pyridazin-3(2H)-ones are pyridazine derivatives, being constructed about a six-membered ring which contains two adjacent nitrogen atoms, at positions one and two, and with a carbonyl group at position three. The interest in these nitrogen-rich heterocyclic derivatives arises from the fact that they exhibit a number of promising pharmacological and biological activities. These include anti-oxidant (Khokra et al., 2016), anti-bacterial and anti-fungal (Abiha et al. 2018), anti-cancer (Kamble et al. 2017), analgesic and anti-inflammatory (Ibrahim et al. 2017), anti-depressant (Boukharsa et al. 2016) and anti-ulcer activities (Yamada et al., 1981). In addition, a number of pyridazinone derivatives have been reported to have potential as agrochemicals, for example as insecticides (Nauen & Bretschneider, 2002), acaricides (Igarashi & Sakamoto, 1994) and herbicides (Azaari et al., 2016). Given the interest in this class of compound and the paucity in structural data (see Database survey), the crystal and molecular structures of the the title pyridazin-3(2H)-one derivative, (I), has been undertaken along with an analysis of the calculated Hirshfeld surface in order to gain further insight into the molecular packing.
2. Structural commentary
The molecular structure of (I), Fig. 1, comprises a central oxopyridazinyl ring connected to an ethylacetate group at the N1 atom, a methyl group at the C2 position and a benzyl residue at the C3 atom. The oxopyridazinyl ring is almost planar, having an r.m.s. deviation of 0.0047 Å for the ring atoms, with the maximum deviation from the ring being 0.0072 (6) Å for the C3 atom; the O1 atom lies 0.0260 (13) Å out of the plane in the same direction as the C3 atom. The ethyl acetate group is close to planar with the r.m.s. deviation for the O2,O3,C12–C16 atoms being 0.0476 Å [the maximum deviation from the least-squares plane is 0.0711 (7) Å for the O3 atom]. The dihedral angle between the two mentioned planes is 77.48 (3)°, indicating an approximately orthogonal relationship. The ethyl acetate group lies to one side of the central plane, as seen in the value of the N2—N1—C13—C14 torsion angle of 104.34 (9)°. The benzyl ring forms a dihedral angle of 76.94 (3)° with the central ring, also indicating an approximately orthogonal relationship but, in this case, the benzyl ring is bisected by the pseudo mirror plane passing through the oxopyridazinyl ring. Consistent with this, the pendant groups form a dihedral angle of 69.74 (3)°. Within the ester group, it is the carboxylate-O3 atom that is directed away from the oxopyridazinyl ring so that the carbonyl-O1 and O2 atoms are proximate, at least to a first approximation.
3. Supramolecular features
The molecular packing of (I) reveals a prominent role for the N1-bound methylene group as each hydrogen atom of this residue participates in a methylene-C13—H⋯O1(ring carbonyl) or N2(pyridazinyl) interaction, Table 1, leading to ten-membered {⋯OCNCH}2 and eight-membered {⋯NNCH}2 synthons, respectively. The result is the formation of a supramolecular tape orientated along the a-axis direction, Fig. 2(a). Globally, the tapes assemble into layers in the ab plane and these stack along the c-axis direction as shown in Fig. 2(b). Weak interactions contributing to the formation of the layers include methyl-C16—H⋯O1(ring carbonyl) contacts (Table 2). Between layers are weak contacts of the type phenyl-C8, C9—H⋯O2(ester carbonyl), phenyl-C10⋯O1(ring carbonyl) and π–π between the oxopyridazinyl and phenyl ring [inter-centroid separation = 3.9573 (7) Å, angle of inclination = 15.00 (4)° for − x, + y, − z]. These interactions are discussed further in the section Hirshfeld surface analysis.
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4. Hirshfeld surface analysis
The Hirshfeld surfaces calculated for (I) were performed in accord with recent studies (Tan et al., 2019) in order to provide complementary information on the influence of short interatomic contacts on the molecular packing. On the Hirshfeld surfaces mapped over dnorm in Fig. 3(a), the C—H⋯N contact involving the methylene-H13A and pyridazinyl-N2 atoms are represented as bright-red spots on the surface. The diminutive red spots appearing near the methylene-H13B and carbonyl-O1 atoms indicate the weak C—H⋯O contact, Fig. 3(a) and (b). The intense blue and red regions corresponding to positive and negative electrostatic potentials on the Hirshfeld surfaces mapped over electrostatic potential in Fig. 4 also represent the donors and acceptors of the above intermolecular interactions, respectively. The influence of the short interatomic O⋯H/H⋯O, C⋯H/H⋯C and C⋯C contacts, as summarized in Table 2, are viewed as the faint-red spots on the dnorm-mapped Hirshfeld surfaces in Fig. 3. The environment of short interatomic O⋯H/H⋯O, C⋯H/H⋯C and C⋯C contacts about the reference molecule within dnorm mapped Hirshfeld surface illustrating weak intermolecular interactions are shown in the views of Fig. 5.
The overall two-dimensional fingerprint plot, Fig. 6(a), and those delineated into H⋯H, O⋯H/H⋯O, N⋯H/H⋯N and C⋯H/H⋯C and C⋯C contacts (McKinnon et al., 2007) are illustrated in Fig. 6(b)–(f); the percentage contribution from different interatomic contacts to the Hirshfeld surfaces of (I) are summarized in Table 3. In the fingerprint plot delineated into H⋯H contacts shown in Fig. 6(b), having the greatest contribution, i.e. 52.2%, to the Hirshfeld surface, a pair of beak-shaped tips at de + di ∼2.3 Å reflect the short interatomic contact between the methyl-H5C and H16C atoms, Table 2. The fingerprint plot delineated into O⋯H/H⋯O contacts in Fig. 6(c) demonstrates two pairs of adjoining short tips at de + di ∼2.5 and 2.6 Å, together with the green aligned points in the central region, which are indicative of weak C—H⋯O contacts present in the crystal. The pair of long spikes at de + di ∼2.5 Å in the fingerprint plot delineated into N⋯H/H⋯N contacts of Fig. 6(d), are the result of a potential C—H⋯N interaction involving the methylene-C13—H13A and pyridazinyl-N2 atoms. The short interatomic C⋯H/H⋯C contacts as summarized in Table 2 are represented by a pair of forceps-like and parabolic tips a de + di ∼2.7 and 2.8 Å, respectively in Fig. 6(e). The presence of a weak π–π contact between the oxopyridazinyl and phenyl rings is reflected in the thick arrow-like tip at de + di ∼3.4 Å in the fingerprint plot delineated into C⋯C contacts of Fig. 6(f), specifically the short interatomic C2⋯C9 contact, Table 2, and the small but notable, i.e. 2.3%, contribution from C⋯N/N⋯C contacts to the Hirshfeld surface.
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5. Database survey
The most closely related structure to (I) in the crystallographic literature is compound (II) whereby the benzyl group of (I) is substituted by a (5-chloro-1-benzofuran-2-yl)methyl) group (Aydın et al., 2007). The structure of (II) presents the same features as for (I) but, with the ester-carbonyl atom directed away from the ring carbonyl group as highlighted in the overlay diagram of Fig. 7.
6. Synthesis and crystallization
A mixture of 3-benzylidene-4-oxopentanoic acid (0.05 mol) and hydrazine hydrate (0.1 mol) in ethanol (100 ml) was refluxed for 2 h. The precipitate formed was filtered off and recrystallized from acetone to obtain the 5-benzyl-6-methylpyridazin-3(2H)-one precursor. To this pyridazine (0.05 mol) was added potassium carbonate (0.1 mmol), tetrabutylammonium bromide (0.01 mmol) and 2-ethyl bromoacetate (0.1 mol) in dimethylformamide (20 ml). The mixture was stirred for 24 h at room temperature. At the end of the reaction, the solution was filtered and the solvent evaporated under reduced pressure. The residue was washed with water and methylenechloride. The solvent was removed and colourless blocks of (I) were obtained by recrystallization of the product from its acetone solution.
7. details
Crystal data, data collection and structure . The carbon-bound H atoms were placed in calculated positions (C—H = 0.95–0.99 Å) and included in the in the riding model approximation, with Uiso(H) set to 1.2–1.5Ueq(C).
details are summarized in Table 4Supporting information
CCDC reference: 1897511
https://doi.org/10.1107/S205698901900241X/hb7802sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698901900241X/hb7802Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S205698901900241X/hb7802Isup3.cml
Data collection: APEX3 (Bruker, 2016); cell
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: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).C16H18N2O3 | F(000) = 608 |
Mr = 286.32 | Dx = 1.298 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 7.4069 (9) Å | Cell parameters from 9950 reflections |
b = 8.1959 (10) Å | θ = 2.6–29.2° |
c = 24.133 (3) Å | µ = 0.09 mm−1 |
β = 90.295 (2)° | T = 120 K |
V = 1465.0 (3) Å3 | Block, colourless |
Z = 4 | 0.37 × 0.29 × 0.24 mm |
Bruker SMART APEX CCD diffractometer | 3966 independent reflections |
Graphite monochromator | 3354 reflections with I > 2σ(I) |
Detector resolution: 8.3333 pixels mm-1 | Rint = 0.028 |
φ and ω scans | θmax = 29.3°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −10→10 |
Tmin = 0.91, Tmax = 0.98 | k = −11→11 |
27503 measured reflections | l = −32→32 |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.120 | w = 1/[σ2(Fo2) + (0.0785P)2 + 0.123P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
3966 reflections | Δρmax = 0.43 e Å−3 |
192 parameters | Δρmin = −0.15 e Å−3 |
0 restraints |
Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = –30.00 and 210.00°. The scan time was 15 sec/frame. |
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 | ||
O1 | 0.46272 (9) | 0.53825 (9) | 0.41137 (3) | 0.02901 (19) | |
O2 | 0.76767 (11) | 0.83037 (9) | 0.40668 (3) | 0.02903 (18) | |
O3 | 0.73810 (9) | 0.88740 (8) | 0.49738 (3) | 0.02266 (17) | |
N1 | 0.76025 (10) | 0.49470 (9) | 0.42943 (3) | 0.01813 (17) | |
N2 | 0.92321 (10) | 0.42213 (9) | 0.42082 (3) | 0.01830 (17) | |
C1 | 0.60366 (12) | 0.46663 (11) | 0.39934 (4) | 0.02018 (19) | |
C2 | 0.93494 (12) | 0.31446 (11) | 0.38109 (4) | 0.01719 (18) | |
C3 | 0.78234 (12) | 0.27085 (10) | 0.34652 (4) | 0.01715 (18) | |
C4 | 0.62344 (12) | 0.34749 (11) | 0.35575 (4) | 0.01990 (19) | |
H4 | 0.5223 | 0.3222 | 0.3329 | 0.024* | |
C5 | 1.11600 (13) | 0.23628 (12) | 0.37348 (4) | 0.0240 (2) | |
H5A | 1.2046 | 0.2896 | 0.3977 | 0.036* | |
H5B | 1.1535 | 0.2479 | 0.3348 | 0.036* | |
H5C | 1.1083 | 0.1202 | 0.3829 | 0.036* | |
C6 | 0.80584 (13) | 0.14014 (11) | 0.30267 (4) | 0.0217 (2) | |
H6A | 0.9049 | 0.1729 | 0.2776 | 0.026* | |
H6B | 0.8421 | 0.0371 | 0.3210 | 0.026* | |
C7 | 0.63798 (13) | 0.10948 (11) | 0.26856 (4) | 0.01965 (19) | |
C8 | 0.61870 (13) | 0.18014 (11) | 0.21636 (4) | 0.0222 (2) | |
H8 | 0.7153 | 0.2417 | 0.2012 | 0.027* | |
C9 | 0.45975 (15) | 0.16155 (12) | 0.18614 (4) | 0.0277 (2) | |
H9 | 0.4485 | 0.2100 | 0.1505 | 0.033* | |
C10 | 0.31775 (15) | 0.07256 (13) | 0.20780 (5) | 0.0314 (2) | |
H10 | 0.2081 | 0.0621 | 0.1875 | 0.038* | |
C11 | 0.33642 (14) | −0.00130 (13) | 0.25926 (5) | 0.0306 (2) | |
H11 | 0.2401 | −0.0642 | 0.2739 | 0.037* | |
C12 | 0.49596 (14) | 0.01645 (12) | 0.28948 (4) | 0.0253 (2) | |
H12 | 0.5082 | −0.0351 | 0.3246 | 0.030* | |
C13 | 0.75566 (13) | 0.61201 (11) | 0.47460 (4) | 0.01904 (19) | |
H13A | 0.8627 | 0.5955 | 0.4987 | 0.023* | |
H13B | 0.6466 | 0.5924 | 0.4972 | 0.023* | |
C14 | 0.75378 (12) | 0.78657 (11) | 0.45400 (4) | 0.01866 (19) | |
C15 | 0.74349 (16) | 1.06125 (11) | 0.48474 (4) | 0.0277 (2) | |
H15A | 0.6350 | 1.0933 | 0.4632 | 0.033* | |
H15B | 0.8518 | 1.0871 | 0.4625 | 0.033* | |
C16 | 0.74939 (16) | 1.15128 (12) | 0.53893 (5) | 0.0305 (2) | |
H16A | 0.6443 | 1.1210 | 0.5612 | 0.046* | |
H16B | 0.7475 | 1.2690 | 0.5319 | 0.046* | |
H16C | 0.8602 | 1.1225 | 0.5590 | 0.046* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0213 (3) | 0.0338 (4) | 0.0318 (4) | 0.0072 (3) | −0.0028 (3) | −0.0136 (3) |
O2 | 0.0441 (5) | 0.0257 (4) | 0.0173 (4) | 0.0028 (3) | 0.0022 (3) | 0.0014 (3) |
O3 | 0.0351 (4) | 0.0156 (3) | 0.0173 (3) | 0.0007 (3) | 0.0015 (3) | −0.0014 (2) |
N1 | 0.0196 (4) | 0.0183 (4) | 0.0164 (4) | 0.0021 (3) | −0.0026 (3) | −0.0039 (3) |
N2 | 0.0188 (4) | 0.0188 (3) | 0.0173 (4) | 0.0016 (3) | −0.0010 (3) | 0.0014 (3) |
C1 | 0.0195 (4) | 0.0211 (4) | 0.0200 (4) | 0.0010 (3) | −0.0018 (3) | −0.0034 (3) |
C2 | 0.0192 (4) | 0.0172 (4) | 0.0151 (4) | 0.0014 (3) | −0.0004 (3) | 0.0027 (3) |
C3 | 0.0218 (4) | 0.0151 (4) | 0.0145 (4) | −0.0001 (3) | −0.0001 (3) | 0.0003 (3) |
C4 | 0.0203 (4) | 0.0204 (4) | 0.0190 (4) | 0.0002 (3) | −0.0033 (3) | −0.0043 (3) |
C5 | 0.0208 (4) | 0.0282 (5) | 0.0229 (5) | 0.0064 (4) | −0.0006 (4) | −0.0002 (4) |
C6 | 0.0252 (5) | 0.0194 (4) | 0.0206 (5) | 0.0032 (3) | −0.0001 (4) | −0.0052 (3) |
C7 | 0.0253 (5) | 0.0162 (4) | 0.0175 (4) | 0.0008 (3) | 0.0012 (3) | −0.0045 (3) |
C8 | 0.0290 (5) | 0.0188 (4) | 0.0188 (4) | −0.0001 (3) | 0.0031 (4) | −0.0022 (3) |
C9 | 0.0366 (6) | 0.0256 (5) | 0.0208 (5) | 0.0050 (4) | −0.0034 (4) | −0.0053 (4) |
C10 | 0.0298 (5) | 0.0295 (5) | 0.0350 (6) | 0.0000 (4) | −0.0071 (4) | −0.0138 (4) |
C11 | 0.0304 (5) | 0.0245 (5) | 0.0370 (6) | −0.0081 (4) | 0.0061 (4) | −0.0089 (4) |
C12 | 0.0346 (5) | 0.0202 (4) | 0.0212 (5) | −0.0032 (4) | 0.0047 (4) | −0.0022 (3) |
C13 | 0.0244 (4) | 0.0181 (4) | 0.0146 (4) | 0.0004 (3) | −0.0019 (3) | −0.0026 (3) |
C14 | 0.0187 (4) | 0.0201 (4) | 0.0172 (4) | 0.0004 (3) | −0.0009 (3) | −0.0023 (3) |
C15 | 0.0412 (6) | 0.0157 (4) | 0.0261 (5) | 0.0018 (4) | 0.0013 (4) | 0.0011 (4) |
C16 | 0.0397 (6) | 0.0185 (5) | 0.0332 (6) | 0.0025 (4) | 0.0003 (4) | −0.0054 (4) |
O1—C1 | 1.2336 (11) | C7—C8 | 1.3932 (13) |
O2—C14 | 1.2020 (11) | C7—C12 | 1.3958 (13) |
O3—C14 | 1.3392 (10) | C8—C9 | 1.3901 (14) |
O3—C15 | 1.4577 (11) | C8—H8 | 0.9500 |
N1—N2 | 1.3625 (10) | C9—C10 | 1.3846 (16) |
N1—C1 | 1.3845 (12) | C9—H9 | 0.9500 |
N1—C13 | 1.4541 (11) | C10—C11 | 1.3878 (16) |
N2—C2 | 1.3063 (11) | C10—H10 | 0.9500 |
C1—C4 | 1.4434 (12) | C11—C12 | 1.3930 (15) |
C2—C3 | 1.4463 (12) | C11—H11 | 0.9500 |
C2—C5 | 1.4985 (12) | C12—H12 | 0.9500 |
C3—C4 | 1.3535 (13) | C13—C14 | 1.5145 (12) |
C3—C6 | 1.5164 (12) | C13—H13A | 0.9900 |
C4—H4 | 0.9500 | C13—H13B | 0.9900 |
C5—H5A | 0.9800 | C15—C16 | 1.5020 (14) |
C5—H5B | 0.9800 | C15—H15A | 0.9900 |
C5—H5C | 0.9800 | C15—H15B | 0.9900 |
C6—C7 | 1.5088 (13) | C16—H16A | 0.9800 |
C6—H6A | 0.9900 | C16—H16B | 0.9800 |
C6—H6B | 0.9900 | C16—H16C | 0.9800 |
C14—O3—C15 | 115.91 (7) | C7—C8—H8 | 119.6 |
N2—N1—C1 | 126.01 (7) | C10—C9—C8 | 120.17 (10) |
N2—N1—C13 | 115.28 (7) | C10—C9—H9 | 119.9 |
C1—N1—C13 | 118.70 (7) | C8—C9—H9 | 119.9 |
C2—N2—N1 | 117.97 (7) | C9—C10—C11 | 119.69 (10) |
O1—C1—N1 | 120.34 (8) | C9—C10—H10 | 120.2 |
O1—C1—C4 | 125.64 (8) | C11—C10—H10 | 120.2 |
N1—C1—C4 | 114.00 (8) | C10—C11—C12 | 120.21 (10) |
N2—C2—C3 | 122.39 (8) | C10—C11—H11 | 119.9 |
N2—C2—C5 | 116.22 (8) | C12—C11—H11 | 119.9 |
C3—C2—C5 | 121.39 (8) | C11—C12—C7 | 120.44 (9) |
C4—C3—C2 | 117.90 (8) | C11—C12—H12 | 119.8 |
C4—C3—C6 | 123.08 (8) | C7—C12—H12 | 119.8 |
C2—C3—C6 | 119.01 (8) | N1—C13—C14 | 112.26 (7) |
C3—C4—C1 | 121.70 (8) | N1—C13—H13A | 109.2 |
C3—C4—H4 | 119.1 | C14—C13—H13A | 109.2 |
C1—C4—H4 | 119.1 | N1—C13—H13B | 109.2 |
C2—C5—H5A | 109.5 | C14—C13—H13B | 109.2 |
C2—C5—H5B | 109.5 | H13A—C13—H13B | 107.9 |
H5A—C5—H5B | 109.5 | O2—C14—O3 | 124.51 (9) |
C2—C5—H5C | 109.5 | O2—C14—C13 | 126.38 (8) |
H5A—C5—H5C | 109.5 | O3—C14—C13 | 109.09 (7) |
H5B—C5—H5C | 109.5 | O3—C15—C16 | 107.38 (8) |
C7—C6—C3 | 113.65 (7) | O3—C15—H15A | 110.2 |
C7—C6—H6A | 108.8 | C16—C15—H15A | 110.2 |
C3—C6—H6A | 108.8 | O3—C15—H15B | 110.2 |
C7—C6—H6B | 108.8 | C16—C15—H15B | 110.2 |
C3—C6—H6B | 108.8 | H15A—C15—H15B | 108.5 |
H6A—C6—H6B | 107.7 | C15—C16—H16A | 109.5 |
C8—C7—C12 | 118.70 (9) | C15—C16—H16B | 109.5 |
C8—C7—C6 | 120.30 (8) | H16A—C16—H16B | 109.5 |
C12—C7—C6 | 120.94 (9) | C15—C16—H16C | 109.5 |
C9—C8—C7 | 120.76 (9) | H16A—C16—H16C | 109.5 |
C9—C8—H8 | 119.6 | H16B—C16—H16C | 109.5 |
C1—N1—N2—C2 | −0.81 (13) | C3—C6—C7—C8 | 98.97 (10) |
C13—N1—N2—C2 | 179.38 (7) | C3—C6—C7—C12 | −78.09 (11) |
N2—N1—C1—O1 | 179.08 (9) | C12—C7—C8—C9 | 1.41 (13) |
C13—N1—C1—O1 | −1.11 (13) | C6—C7—C8—C9 | −175.72 (8) |
N2—N1—C1—C4 | 0.48 (13) | C7—C8—C9—C10 | 0.24 (14) |
C13—N1—C1—C4 | −179.71 (8) | C8—C9—C10—C11 | −1.55 (15) |
N1—N2—C2—C3 | 0.03 (12) | C9—C10—C11—C12 | 1.21 (15) |
N1—N2—C2—C5 | −179.33 (8) | C10—C11—C12—C7 | 0.46 (15) |
N2—C2—C3—C4 | 1.02 (13) | C8—C7—C12—C11 | −1.75 (14) |
C5—C2—C3—C4 | −179.66 (8) | C6—C7—C12—C11 | 175.35 (9) |
N2—C2—C3—C6 | −177.78 (8) | N2—N1—C13—C14 | 104.34 (9) |
C5—C2—C3—C6 | 1.55 (12) | C1—N1—C13—C14 | −75.50 (10) |
C2—C3—C4—C1 | −1.34 (13) | C15—O3—C14—O2 | −1.63 (13) |
C6—C3—C4—C1 | 177.40 (8) | C15—O3—C14—C13 | 176.99 (8) |
O1—C1—C4—C3 | −177.86 (9) | N1—C13—C14—O2 | −5.26 (14) |
N1—C1—C4—C3 | 0.65 (13) | N1—C13—C14—O3 | 176.15 (7) |
C4—C3—C6—C7 | 2.78 (13) | C14—O3—C15—C16 | −172.44 (8) |
C2—C3—C6—C7 | −178.49 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13A···N2i | 0.99 | 2.51 | 3.4704 (13) | 165 |
C13—H13B···O1ii | 0.99 | 2.59 | 3.4281 (13) | 143 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z+1. |
Contact | Distance | Symmetry operation |
H5C···H16C | 2.29 | 2 - x, 1 - y, 1 - z |
O1···H10 | 2.58 | 1/2 - x, 1/2 + y, 1/2 - z |
O1···H16B | 2.55 | 1 - x, 2 - y, 1 - z |
O2···H8 | 2.63 | 3/2 - x, 1/2 + y, 1/2 - z |
O2···H9 | 2.63 | 3/2 - x, 1/2 + y, 1/2 - z |
C2···H1B5 | 2.71 | x, -1 + y, z |
C9···H11 | 2.73 | 1/2 - x, 1/2 + y, 1/2 - z |
C10···H5B | 2.81 | 3/2 - x, -1/2 + y, 1/2 - z |
C2···C9 | 3.3683 (14) | 3/2 - x, 1/2 + y, 1/2 - z |
Contact | Percentage contribution |
H···H | 52.2 |
O···H/H···O | 23.3 |
C···H/H···C | 14.7 |
N···H/H···N | 6.6 |
C···C | 2.9 |
C···N/N···C | 0.3 |
Footnotes
‡Additional correspondence author, e-mail: y.ramli@um5s.net.ma.
Acknowledgements
YR thanks Mohammed V University for the support of the Drug Sciences Research Center. JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.
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