The molecular and crystal structures of (I), C20H19N3O2, and (II), C22H21N3O, are similar because they differ only in the substituent at the hydrazide N atom where a phenylmethylene moiety for (II) is present instead of a furanmethylene moiety for (I).
Keywords: crystal structure, hydrogen bond, benzohydrazide, C—H⋯π(ring), mefenamic, NSAIDs
Abstract
The conformation about the central benzene ring in the molecule of (I), C20H19N3O2, is partially determined by an intramolecular N—H⋯O hydrogen bond. In the crystal, chains parallel to the c axis are generated by intermolecular N—H⋯O hydrogen bonds with the chains assembled into a three-dimensional network structure by intermolecular C—H⋯O hydrogen bonds and C—H⋯π(ring) interactions. The molecule of (II), C22H21N3O, differs from (I) only in the substituent at the hydrazide N atom where a phenylmethylene moiety for (II) is present instead of a furanmethylene moiety for (I). Hence, molecules of (I) and (II) show similarities in their molecular and crystal structures. The conformation of the central portion of the molecule of (II) is also therefore partially determined by an intramolecular N—H⋯O hydrogen bond and intermolecular N—H⋯O hydrogen bonds form chains parallel to the c axis. Likewise, the chains are connected into a three-dimensional network by C—H⋯O hydrogen bonds and C—H⋯π(ring) interactions.
Chemical context
Hydrazones possess a wide variety of biological activities such as anticonvulsant (Kumar et al., 2010 ▸), anti-depressant (Mohareb et al., 2010 ▸), analgesic, anti-inflammatory (Hernandez et al., 2012 ▸), antimicrobial (Maguene et al., 2011 ▸), anticancer (Al-Said et al., 2011 ▸) or antiparasitic (Siddiqui et al., 2012 ▸) properties. A better tolerated and potent non-steroidal anti-inflammatory drug (NSAID) with fewer side effect characteristic is mefenamic acid. This drug belongs to the most commonly prescribed medications worldwide for treatment of painful inflammatory conditions such as rheumatic arthritis, traumatic injuries, pain and fever (Abbas, 2017 ▸). It is also used to treat mild to moderate pain, including menstrual pain and the associated migraines (Pringsheim et al., 2008 ▸). With this background in mind, we report here the synthesis and crystal structural determination of two hydrazide derivatives of mefenamic acid, (I) and (II).
Structural commentary
In the molecule of (I) (Fig. 1 ▸), the dihedral angles between the central C9–C14 benzene ring and the C1–C6 and C17–C20/O2 rings are, respectively, 51.90 (6) and 43.32 (8)°. The conformation about the central portion of the molecule is partially determined by the intramolecular N1—H1⋯O1 hydrogen bond (Table 1 ▸).
Figure 1.
The molecule of (I) with atom-labeling scheme and displacement ellipsoids drawn at the 50% probability level. The intramolecular N—H⋯O hydrogen bond is shown as a dashed line.
Table 1. Hydrogen-bond geometry (Å, °) for (I) .
Cg1 and Cg2 are the centroids of the C17–C20/O2 and C1–C6 rings, respectively.
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| N1—H1⋯O1 | 0.910 (19) | 1.977 (18) | 2.7045 (14) | 135.8 (15) |
| N2—H2⋯O1i | 0.883 (18) | 2.014 (18) | 2.8458 (13) | 156.4 (15) |
| C4—H4⋯Cg1ii | 0.955 (17) | 2.941 (17) | 3.7248 (15) | 140.1 (17) |
| C6—H6⋯O1iii | 0.976 (18) | 2.556 (18) | 3.3434 (16) | 137.7 (14) |
| C11—H11⋯Cg2iv | 0.996 (16) | 2.765 (16) | 3.6231 (14) | 144.8 (12) |
Symmetry codes: (i) x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}; (ii) -x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}; (iii) -x+1, -y+1, -z+1; (iv) x, y, z+1.
Molecule (II) (Fig. 2 ▸) differs from molecule (I) only by the substituent at N3, i.e. a phenylmethylene moiety for (II) instead of a furanmethylene moiety for (I). Hence, the structural characteristics for most parts of the two molecules are very similar, as exemplified by the dihedral angles between the central C9–C14 benzene ring and the C1–C6 and C17–C22 benzene rings of 57.38 (6) and 43.48 (6)°, respectively, observed in molecule (II). Likewise, in the crystal of (II), the conformation of the central portion of the molecule is also partially determined by the intramolecular N1—H1⋯O1 hydrogen bond (Table 2 ▸; Fig. 2 ▸).
Figure 2.
The molecule of (II) with atom-labeling scheme and displacement ellipsoids drawn at the 50% probability level. The intramolecular N—H⋯O hydrogen bond is shown by a dashed line.
Table 2. Hydrogen-bond geometry (Å, °) for (II) .
Cg1 and Cg3 are the centroids of the C1–C6 and C17–C22 benzene rings, respectively.
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| N1—H1⋯O1 | 0.908 (18) | 1.946 (18) | 2.6920 (13) | 138.2 (15) |
| N2—H2⋯O1i | 0.913 (16) | 1.974 (17) | 2.8564 (13) | 162.0 (14) |
| C4—H4⋯Cg3ii | 1.001 (17) | 2.796 (17) | 3.6141 (15) | 139.4 (13) |
| C6—H6⋯O1iii | 0.980 (18) | 2.583 (19) | 3.4815 (16) | 152.5 (13) |
| C20—H20⋯Cg1iv | 1.000 (18) | 2.838 (17) | 3.6644 (15) | 140.5 (13) |
Symmetry codes: (i) x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}; (ii) -x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}; (iii) -x+1, -y+1, -z+1; (iv) x-1, -y-{\script{1\over 2}}, z-{\script{3\over 2}}.
Supramolecular features
In the crystal structure of (I), chains of molecules extending parallel to the c-axis direction are generated by N2—H2⋯O2 hydrogen bonds (Table 1 ▸; Fig. 3 ▸). These chains are linked into a three-dimensional network structure by a combination of C6—H6⋯O1 hydrogen bonds and C4—H4⋯Cg1 and C11—H11⋯Cg2 interactions (Table 1 ▸; Fig. 4 ▸).
Figure 3.
A portion of one N—H⋯O hydrogen-bonded chain viewed along the b axis of (I) with hydrogen bonds shown as dashed lines.
Figure 4.
Packing view of (I) along the c axis with intermolecular C—H⋯O hydrogen bonds shown as dashed lines.
In the crystal structure of (II), intermolecular N2—H2⋯O1 hydrogen bonds form chains parallel the c-axis direction (Table 2 ▸; Fig. 5 ▸), which are connected through C6—H6⋯O1 hydrogen bonds and C4—H4⋯Cg3 and C20—H20⋯Cg1 interactions to form a three-dimensional network (Table 2 ▸; Fig. 6 ▸).
Figure 5.
A portion of the N—H⋯O hydrogen-bonded chain viewed along the b axis of (II) with hydrogen bonds shown as dashed lines..
Figure 6.
Packing view of (II) along the c axis with intermolecular C—H⋯O hydrogen bonds shown as dashed lines.
Database survey
A search of the Cambridge Structural Database (CSD, version 5.42, November 2020; Groom et al., 2016 ▸) gave six hits for structures with a 2-(2,3-dimethylanilino)-N′-methylidenebenzohydrazide skeleton: N′-[(4-chlorophenyl)methylidene]-2-[(2,3-dimethylphenyl)amino]benzohydrazide (VEDBAK; Jasinski et al., 2017 ▸), N′-[1-(4-chlorophenyl)ethylidene]-2-[(2,3-dimethylphenyl)amino]benzohydrazide (LEBSET; Mohamed et al., 2017 ▸), 2-[(2,3-dimethylphenyl)amino]-N′-(2-hydroxybenzylidene)benzohydrazide (DABREG; Mohamed et al., 2015 ▸), 2-[(2,3-dimethylphenyl)amino]-N′-(2-thienylmethylene)benzohydrazide (LEGHAI; Fun et al., 2012a ▸), 2-[(2,3-dimethylphenyl)amino]benzohydrazide (LEGHIQ; Fun et al., 2012b ▸) and (E)-2-[(2,3-dimethylphenyl)amino]-N′-(2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-ylidene)benzohydrazide (YAXJUE; Bhat et al., 2012 ▸).
In the structure of VEDBAK, the dihedral angle between the planes of the chlorophenyl and dimethylphenyl rings is 66.50 (9)°. These rings make dihedral angles of 47.79 (8) and 69.24 (9)°, respectively, with the central benzene ring. In the crystal structure of VEDBAK, molecules are linked into a three-dimensional supramolecular network by N—H⋯O, C—H⋯O hydrogen bonds and weak C—H⋯π interactions.
In the crystal structure of LEBSET, molecules are linked into a three-dimensional supramolecular network by N—H⋯N, N—H⋯O, C—H⋯O hydrogen bonds and weak C—H⋯π interactions.
The asymmetric unit of DABREG consists of two molecules (A and B) having differing conformations that mainly concern the dihedral angles between the hydroxyphenyl and dimethylphenyl rings relative to the central phenylene ring, with values of 30.16 (6) and 58.60 (6)° in molecule A and of 13.42 (7) and 60.31 (7)° in molecule B. With the exception of the dimethylphenyl substituent, the conformations of the rest of each molecule are largely determined by intramolecular O—H⋯N and N—H⋯O hydrogen bonds. In the crystal structure, N—H⋯O hydrogen bonds link the molecules into chains extending parallel to the a axis where the types of molecules alternate in an ⋯A⋯B⋯A⋯B⋯ fashion.
In LEGHAI, the central benzene ring makes dihedral angles of 45.36 (9) and 55.33 (9)° with the thiophene ring and the dimethyl-substituted benzene ring, respectively. The dihedral angle between the thiophene ring and dimethyl-substituted benzene ring is 83.60 (9)°. The thiophene ring and the benzene ring are twisted from the mean plane of the C(=O)—N—N=C bridge [maximum deviation = 0.0860 (13) Å], with dihedral angles of 23.86 (9) and 24.77 (8)°, respectively. An intramolecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal structure of LEGHAI, molecules are linked by N—H⋯O and C—H⋯O hydrogen bonds to the same acceptor atom, forming sheets lying parallel to the bc plane. The crystal packing also features C—H⋯π interactions.
In LEGHIQ, the dihedral angle between the benzene rings is 58.05 (9)°. The non-H atoms of the hydrazide group lie in a common plane (r.m.s. deviation = 0.0006 Å) and are close to co-planar with their attached benzene ring [dihedral angle = 8.02 (9)°]. An intramolecular N—H⋯O hydrogen bond generates an S(6) ring motif in the molecule, and a short intramolecular contact (H⋯H = 1.88 Å) is also observed. In the crystal structure of LEGHIQ, molecules are linked by pairs of N—H⋯N hydrogen bonds into inversion dimers. The crystal packing also features C—H⋯π interactions.
The asymmetric unit of the compound YAXJUE comprises two molecules. The dihedral angles between the benzene rings in the two molecules are 59.7 (2) and 61.27 (18)°. The cyclohexene rings adopt sofa and half-chair conformations. In the crystal structure of YAXJUE, molecules are connected via N—H⋯O and weak C—H⋯O hydrogen bonds, forming chains along the a-axis direction. In each molecule, there is an intramolecular N—H⋯O hydrogen bond.
Synthesis and crystallization
Synthesis of (I): A mixture of 1 mmol of 2-furaldehyde (96 mg) and 1 mmol of 2-[(2,3-dimethylphenyl)amino]benzohydrazide (255 mg) in 20 ml of ethanol was refluxed and monitored by TLC until completion. The reaction mixture was cooled to room temperature when the solid product was obtained. The crude product was filtered off, dried and recrystallized from ethanol to afford crystals suitable for X-ray diffraction. M.p. 479–483 K.
Synthesis of (II): In a solution of 20 ml of ethanol, a mixture of 106 mg (1 mmol) of benzaldehyde (106 mg) and 255 mg (1 mmol) of 2-[(2,3-dimethylphenyl)amino]benzohydrazide was refluxed for 4 h. The solid product was obtained after the reaction mixture was cooled to room temperature. The crude product was filtered off, dried and recrystallized from ethanol to afford crystals suitable for X-ray diffraction. M.p. 466–469 K.
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 3 ▸. For (I) and (II), all H atoms were located in a difference-Fourier map and were refined freely.
Table 3. Experimental details.
| (I) | (II) | |
|---|---|---|
| Crystal data | ||
| Chemical formula | C20H19N3O2 | C22H21N3O |
| M r | 333.38 | 343.42 |
| Crystal system, space group | Monoclinic, P21/c | Monoclinic, P21/c |
| Temperature (K) | 150 | 150 |
| a, b, c (Å) | 13.8467 (3), 15.8409 (3), 8.0225 (2) | 14.3493 (8), 15.7501 (9), 8.3737 (5) |
| β (°) | 104.814 (1) | 106.285 (2) |
| V (Å3) | 1701.20 (7) | 1816.55 (18) |
| Z | 4 | 4 |
| Radiation type | Cu Kα | Cu Kα |
| μ (mm−1) | 0.69 | 0.62 |
| Crystal size (mm) | 0.19 × 0.11 × 0.07 | 0.19 × 0.13 × 0.08 |
| Data collection | ||
| Diffractometer | Bruker D8 VENTURE PHOTON 100 CMOS | Bruker D8 VENTURE PHOTON 100 CMOS |
| Absorption correction | Multi-scan (SADABS; Krause et al., 2015 ▸) | Multi-scan (SADABS; Krause et al., 2015 ▸) |
| T min, T max | 0.88, 0.95 | 0.86, 0.95 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 13222, 3372, 2939 | 13875, 3665, 3140 |
| R int | 0.031 | 0.031 |
| (sin θ/λ)max (Å−1) | 0.625 | 0.625 |
| Refinement | ||
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.036, 0.095, 1.05 | 0.037, 0.092, 1.04 |
| No. of reflections | 3372 | 3665 |
| No. of parameters | 303 | 320 |
| H-atom treatment | All H-atom parameters refined | All H-atom parameters refined |
| Δρmax, Δρmin (e Å−3) | 0.23, −0.19 | 0.17, −0.16 |
Supplementary Material
Crystal structure: contains datablock(s) global, I, II. DOI: 10.1107/S2056989021001353/wm5599sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989021001353/wm5599Isup2.hkl
Structure factors: contains datablock(s) II. DOI: 10.1107/S2056989021001353/wm5599IIsup3.hkl
Supporting information file. DOI: 10.1107/S2056989021001353/wm5599Isup4.cml
Supporting information file. DOI: 10.1107/S2056989021001353/wm5599IIsup5.cml
Additional supporting information: crystallographic information; 3D view; checkCIF report
supplementary crystallographic information
3-(2,3-Dimethylanilino)-N'-[(E)-(furan-2-yl)methylidene]benzohydrazide (I) . Crystal data
| C20H19N3O2 | F(000) = 704 |
| Mr = 333.38 | Dx = 1.302 Mg m−3 |
| Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
| a = 13.8467 (3) Å | Cell parameters from 9755 reflections |
| b = 15.8409 (3) Å | θ = 3.3–74.5° |
| c = 8.0225 (2) Å | µ = 0.69 mm−1 |
| β = 104.814 (1)° | T = 150 K |
| V = 1701.20 (7) Å3 | Column, colourless |
| Z = 4 | 0.19 × 0.11 × 0.07 mm |
3-(2,3-Dimethylanilino)-N'-[(E)-(furan-2-yl)methylidene]benzohydrazide (I) . Data collection
| Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 3372 independent reflections |
| Radiation source: INCOATEC IµS micro–focus source | 2939 reflections with I > 2σ(I) |
| Mirror monochromator | Rint = 0.031 |
| Detector resolution: 10.4167 pixels mm-1 | θmax = 74.5°, θmin = 3.3° |
| ω scans | h = −14→16 |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | k = −18→19 |
| Tmin = 0.88, Tmax = 0.95 | l = −9→9 |
| 13222 measured reflections |
3-(2,3-Dimethylanilino)-N'-[(E)-(furan-2-yl)methylidene]benzohydrazide (I) . Refinement
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.036 | All H-atom parameters refined |
| wR(F2) = 0.095 | w = 1/[σ2(Fo2) + (0.0475P)2 + 0.3981P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.05 | (Δ/σ)max < 0.001 |
| 3372 reflections | Δρmax = 0.23 e Å−3 |
| 303 parameters | Δρmin = −0.19 e Å−3 |
| 0 restraints | Extinction correction: SHELXL 2016/6 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0049 (4) |
3-(2,3-Dimethylanilino)-N'-[(E)-(furan-2-yl)methylidene]benzohydrazide (I) . Special details
| 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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
3-(2,3-Dimethylanilino)-N'-[(E)-(furan-2-yl)methylidene]benzohydrazide (I) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.43892 (6) | 0.33178 (5) | 0.45837 (10) | 0.0275 (2) | |
| O2 | 0.10644 (7) | 0.20592 (6) | 0.31256 (12) | 0.0371 (2) | |
| N1 | 0.62923 (8) | 0.38535 (8) | 0.58252 (15) | 0.0353 (3) | |
| H1 | 0.5810 (13) | 0.3629 (11) | 0.495 (2) | 0.051 (5)* | |
| N2 | 0.37222 (7) | 0.26862 (7) | 0.65665 (13) | 0.0262 (2) | |
| H2 | 0.3836 (12) | 0.2485 (11) | 0.763 (2) | 0.043 (4)* | |
| N3 | 0.29029 (7) | 0.24278 (6) | 0.52997 (12) | 0.0260 (2) | |
| C1 | 0.70907 (9) | 0.42610 (8) | 0.53437 (15) | 0.0279 (3) | |
| C2 | 0.76645 (9) | 0.37935 (8) | 0.44626 (15) | 0.0276 (3) | |
| C3 | 0.84199 (9) | 0.42133 (9) | 0.39033 (15) | 0.0313 (3) | |
| C4 | 0.85989 (10) | 0.50619 (9) | 0.42738 (17) | 0.0361 (3) | |
| H4 | 0.9119 (12) | 0.5334 (11) | 0.389 (2) | 0.047 (5)* | |
| C5 | 0.80281 (11) | 0.55168 (9) | 0.51433 (19) | 0.0378 (3) | |
| H5 | 0.8130 (13) | 0.6122 (12) | 0.533 (2) | 0.052 (5)* | |
| C6 | 0.72631 (10) | 0.51191 (9) | 0.56546 (18) | 0.0342 (3) | |
| H6 | 0.6815 (13) | 0.5435 (11) | 0.618 (2) | 0.052 (5)* | |
| C7 | 0.74397 (12) | 0.28753 (9) | 0.40596 (19) | 0.0381 (3) | |
| H7A | 0.6963 (16) | 0.2816 (13) | 0.295 (3) | 0.073 (6)* | |
| H7B | 0.8049 (17) | 0.2542 (14) | 0.398 (3) | 0.078 (6)* | |
| H7C | 0.7169 (13) | 0.2599 (12) | 0.493 (2) | 0.055 (5)* | |
| C8 | 0.90166 (13) | 0.37716 (12) | 0.2834 (2) | 0.0470 (4) | |
| H8A | 0.8587 (14) | 0.3622 (12) | 0.170 (3) | 0.056 (5)* | |
| H8B | 0.957 (2) | 0.4145 (17) | 0.265 (3) | 0.105 (8)* | |
| H8C | 0.9298 (16) | 0.3242 (15) | 0.331 (3) | 0.075 (6)* | |
| C9 | 0.60374 (9) | 0.39480 (8) | 0.73618 (15) | 0.0275 (3) | |
| C10 | 0.66889 (10) | 0.43330 (8) | 0.88024 (16) | 0.0326 (3) | |
| H10 | 0.7324 (13) | 0.4574 (11) | 0.866 (2) | 0.045 (4)* | |
| C11 | 0.64394 (10) | 0.44053 (9) | 1.03499 (16) | 0.0350 (3) | |
| H11 | 0.6916 (11) | 0.4702 (10) | 1.131 (2) | 0.037 (4)* | |
| C12 | 0.55432 (10) | 0.40856 (9) | 1.05579 (16) | 0.0343 (3) | |
| H12 | 0.5341 (11) | 0.4161 (10) | 1.165 (2) | 0.037 (4)* | |
| C13 | 0.48990 (10) | 0.36959 (8) | 0.91722 (16) | 0.0293 (3) | |
| H13 | 0.4250 (12) | 0.3490 (10) | 0.9272 (19) | 0.038 (4)* | |
| C14 | 0.51281 (9) | 0.36090 (7) | 0.75761 (15) | 0.0251 (3) | |
| C15 | 0.44003 (8) | 0.32000 (7) | 0.61193 (14) | 0.0238 (2) | |
| C16 | 0.23183 (9) | 0.19224 (8) | 0.58218 (15) | 0.0280 (3) | |
| H16 | 0.2460 (11) | 0.1729 (10) | 0.701 (2) | 0.038 (4)* | |
| C17 | 0.13770 (9) | 0.16726 (8) | 0.46938 (16) | 0.0297 (3) | |
| C18 | 0.06614 (11) | 0.11334 (10) | 0.4926 (2) | 0.0410 (3) | |
| H18 | 0.0716 (14) | 0.0788 (12) | 0.597 (2) | 0.059 (5)* | |
| C19 | −0.01455 (11) | 0.11896 (10) | 0.3418 (2) | 0.0440 (4) | |
| H19 | −0.0782 (15) | 0.0886 (12) | 0.319 (2) | 0.061 (5)* | |
| C20 | 0.01305 (10) | 0.17477 (10) | 0.2391 (2) | 0.0425 (4) | |
| H20 | −0.0217 (15) | 0.1968 (13) | 0.124 (3) | 0.063 (5)* |
3-(2,3-Dimethylanilino)-N'-[(E)-(furan-2-yl)methylidene]benzohydrazide (I) . Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0276 (4) | 0.0337 (5) | 0.0215 (4) | −0.0028 (3) | 0.0067 (3) | −0.0006 (3) |
| O2 | 0.0308 (5) | 0.0430 (5) | 0.0328 (5) | −0.0046 (4) | −0.0004 (4) | 0.0003 (4) |
| N1 | 0.0289 (6) | 0.0477 (7) | 0.0315 (6) | −0.0131 (5) | 0.0118 (4) | −0.0092 (5) |
| N2 | 0.0236 (5) | 0.0337 (5) | 0.0197 (5) | −0.0034 (4) | 0.0026 (4) | 0.0016 (4) |
| N3 | 0.0225 (5) | 0.0315 (5) | 0.0229 (5) | −0.0018 (4) | 0.0040 (4) | −0.0016 (4) |
| C1 | 0.0224 (6) | 0.0326 (6) | 0.0280 (6) | −0.0021 (5) | 0.0051 (4) | 0.0011 (5) |
| C2 | 0.0266 (6) | 0.0307 (6) | 0.0239 (6) | −0.0007 (5) | 0.0037 (4) | 0.0010 (5) |
| C3 | 0.0236 (6) | 0.0426 (7) | 0.0269 (6) | −0.0005 (5) | 0.0050 (5) | 0.0022 (5) |
| C4 | 0.0288 (7) | 0.0433 (8) | 0.0352 (7) | −0.0101 (6) | 0.0065 (5) | 0.0057 (6) |
| C5 | 0.0387 (8) | 0.0292 (7) | 0.0428 (8) | −0.0044 (5) | 0.0056 (6) | 0.0025 (6) |
| C6 | 0.0295 (7) | 0.0321 (7) | 0.0402 (7) | 0.0025 (5) | 0.0078 (5) | −0.0009 (5) |
| C7 | 0.0498 (9) | 0.0314 (7) | 0.0344 (7) | −0.0032 (6) | 0.0130 (6) | −0.0027 (5) |
| C8 | 0.0392 (9) | 0.0645 (11) | 0.0414 (9) | −0.0004 (7) | 0.0176 (7) | −0.0055 (7) |
| C9 | 0.0250 (6) | 0.0297 (6) | 0.0271 (6) | 0.0004 (5) | 0.0052 (4) | 0.0000 (5) |
| C10 | 0.0260 (6) | 0.0356 (7) | 0.0327 (7) | −0.0025 (5) | 0.0011 (5) | −0.0009 (5) |
| C11 | 0.0358 (7) | 0.0358 (7) | 0.0275 (6) | −0.0008 (5) | −0.0028 (5) | −0.0015 (5) |
| C12 | 0.0411 (7) | 0.0370 (7) | 0.0235 (6) | −0.0008 (6) | 0.0060 (5) | −0.0024 (5) |
| C13 | 0.0301 (7) | 0.0313 (6) | 0.0268 (6) | −0.0012 (5) | 0.0079 (5) | 0.0003 (5) |
| C14 | 0.0232 (6) | 0.0275 (6) | 0.0233 (6) | 0.0009 (4) | 0.0033 (4) | 0.0001 (4) |
| C15 | 0.0217 (6) | 0.0260 (6) | 0.0236 (6) | 0.0023 (4) | 0.0055 (4) | 0.0000 (4) |
| C16 | 0.0264 (6) | 0.0335 (6) | 0.0249 (6) | −0.0010 (5) | 0.0081 (5) | −0.0001 (5) |
| C17 | 0.0272 (6) | 0.0341 (6) | 0.0286 (6) | −0.0013 (5) | 0.0088 (5) | −0.0029 (5) |
| C18 | 0.0342 (7) | 0.0482 (8) | 0.0433 (8) | −0.0102 (6) | 0.0150 (6) | −0.0046 (6) |
| C19 | 0.0250 (7) | 0.0502 (9) | 0.0563 (9) | −0.0075 (6) | 0.0097 (6) | −0.0170 (7) |
| C20 | 0.0285 (7) | 0.0471 (8) | 0.0451 (8) | −0.0014 (6) | −0.0033 (6) | −0.0108 (7) |
3-(2,3-Dimethylanilino)-N'-[(E)-(furan-2-yl)methylidene]benzohydrazide (I) . Geometric parameters (Å, º)
| O1—C15 | 1.2422 (14) | C7—H7C | 0.978 (19) |
| O2—C17 | 1.3663 (16) | C8—H8A | 0.98 (2) |
| O2—C20 | 1.3687 (16) | C8—H8B | 1.01 (3) |
| N1—C9 | 1.3744 (16) | C8—H8C | 0.96 (2) |
| N1—C1 | 1.4165 (16) | C9—C10 | 1.4102 (17) |
| N1—H1 | 0.910 (19) | C9—C14 | 1.4191 (17) |
| N2—C15 | 1.3582 (15) | C10—C11 | 1.3759 (19) |
| N2—N3 | 1.3777 (13) | C10—H10 | 0.993 (17) |
| N2—H2 | 0.883 (18) | C11—C12 | 1.389 (2) |
| N3—C16 | 1.2826 (16) | C11—H11 | 0.996 (16) |
| C1—C6 | 1.3915 (18) | C12—C13 | 1.3804 (18) |
| C1—C2 | 1.4023 (17) | C12—H12 | 0.989 (16) |
| C2—C3 | 1.4063 (17) | C13—C14 | 1.4024 (17) |
| C2—C7 | 1.5053 (18) | C13—H13 | 0.978 (16) |
| C3—C4 | 1.385 (2) | C14—C15 | 1.4829 (15) |
| C3—C8 | 1.507 (2) | C16—C17 | 1.4392 (17) |
| C4—C5 | 1.383 (2) | C16—H16 | 0.973 (16) |
| C4—H4 | 0.955 (17) | C17—C18 | 1.3566 (19) |
| C5—C6 | 1.3818 (19) | C18—C19 | 1.424 (2) |
| C5—H5 | 0.975 (19) | C18—H18 | 0.990 (19) |
| C6—H6 | 0.976 (18) | C19—C20 | 1.330 (2) |
| C7—H7A | 0.97 (2) | C19—H19 | 0.98 (2) |
| C7—H7B | 1.01 (2) | C20—H20 | 0.99 (2) |
| C17—O2—C20 | 106.08 (11) | H8B—C8—H8C | 108.9 (19) |
| C9—N1—C1 | 126.32 (11) | N1—C9—C10 | 121.67 (11) |
| C9—N1—H1 | 115.6 (11) | N1—C9—C14 | 120.45 (11) |
| C1—N1—H1 | 115.8 (11) | C10—C9—C14 | 117.77 (11) |
| C15—N2—N3 | 118.53 (10) | C11—C10—C9 | 121.32 (12) |
| C15—N2—H2 | 120.4 (11) | C11—C10—H10 | 120.6 (10) |
| N3—N2—H2 | 120.9 (11) | C9—C10—H10 | 118.0 (10) |
| C16—N3—N2 | 114.45 (10) | C10—C11—C12 | 121.07 (12) |
| C6—C1—C2 | 120.85 (11) | C10—C11—H11 | 118.0 (9) |
| C6—C1—N1 | 120.43 (11) | C12—C11—H11 | 120.9 (9) |
| C2—C1—N1 | 118.62 (11) | C13—C12—C11 | 118.64 (12) |
| C1—C2—C3 | 118.33 (11) | C13—C12—H12 | 119.6 (9) |
| C1—C2—C7 | 120.39 (11) | C11—C12—H12 | 121.7 (9) |
| C3—C2—C7 | 121.21 (12) | C12—C13—C14 | 121.92 (12) |
| C4—C3—C2 | 119.82 (12) | C12—C13—H13 | 120.1 (9) |
| C4—C3—C8 | 118.60 (13) | C14—C13—H13 | 118.0 (9) |
| C2—C3—C8 | 121.53 (13) | C13—C14—C9 | 119.23 (11) |
| C5—C4—C3 | 121.32 (12) | C13—C14—C15 | 119.71 (11) |
| C5—C4—H4 | 120.2 (10) | C9—C14—C15 | 121.00 (10) |
| C3—C4—H4 | 118.5 (10) | O1—C15—N2 | 121.19 (10) |
| C6—C5—C4 | 119.50 (13) | O1—C15—C14 | 123.33 (10) |
| C6—C5—H5 | 119.7 (10) | N2—C15—C14 | 115.47 (10) |
| C4—C5—H5 | 120.7 (10) | N3—C16—C17 | 120.80 (11) |
| C5—C6—C1 | 120.11 (13) | N3—C16—H16 | 122.0 (9) |
| C5—C6—H6 | 121.1 (11) | C17—C16—H16 | 117.0 (9) |
| C1—C6—H6 | 118.7 (11) | C18—C17—O2 | 109.77 (12) |
| C2—C7—H7A | 110.2 (13) | C18—C17—C16 | 131.50 (13) |
| C2—C7—H7B | 112.8 (13) | O2—C17—C16 | 118.59 (11) |
| H7A—C7—H7B | 106.1 (17) | C17—C18—C19 | 106.60 (14) |
| C2—C7—H7C | 112.1 (11) | C17—C18—H18 | 124.4 (11) |
| H7A—C7—H7C | 108.4 (16) | C19—C18—H18 | 129.0 (11) |
| H7B—C7—H7C | 106.9 (17) | C20—C19—C18 | 106.30 (13) |
| C3—C8—H8A | 110.5 (11) | C20—C19—H19 | 126.7 (11) |
| C3—C8—H8B | 111.0 (15) | C18—C19—H19 | 127.0 (11) |
| H8A—C8—H8B | 108.1 (18) | C19—C20—O2 | 111.25 (13) |
| C3—C8—H8C | 113.8 (13) | C19—C20—H20 | 131.6 (12) |
| H8A—C8—H8C | 104.2 (17) | O2—C20—H20 | 117.1 (12) |
| C15—N2—N3—C16 | 177.81 (11) | C11—C12—C13—C14 | 0.5 (2) |
| C9—N1—C1—C6 | −44.52 (19) | C12—C13—C14—C9 | −1.49 (19) |
| C9—N1—C1—C2 | 139.08 (13) | C12—C13—C14—C15 | −178.79 (12) |
| C6—C1—C2—C3 | 0.10 (18) | N1—C9—C14—C13 | 178.37 (11) |
| N1—C1—C2—C3 | 176.49 (11) | C10—C9—C14—C13 | 2.26 (17) |
| C6—C1—C2—C7 | −177.09 (12) | N1—C9—C14—C15 | −4.36 (18) |
| N1—C1—C2—C7 | −0.70 (18) | C10—C9—C14—C15 | 179.53 (11) |
| C1—C2—C3—C4 | 1.90 (18) | N3—N2—C15—O1 | −12.62 (17) |
| C7—C2—C3—C4 | 179.07 (12) | N3—N2—C15—C14 | 166.53 (10) |
| C1—C2—C3—C8 | −175.36 (12) | C13—C14—C15—O1 | 157.42 (11) |
| C7—C2—C3—C8 | 1.81 (19) | C9—C14—C15—O1 | −19.84 (18) |
| C2—C3—C4—C5 | −1.98 (19) | C13—C14—C15—N2 | −21.70 (16) |
| C8—C3—C4—C5 | 175.36 (13) | C9—C14—C15—N2 | 161.04 (11) |
| C3—C4—C5—C6 | 0.0 (2) | N2—N3—C16—C17 | 173.06 (11) |
| C4—C5—C6—C1 | 2.0 (2) | C20—O2—C17—C18 | 0.28 (15) |
| C2—C1—C6—C5 | −2.09 (19) | C20—O2—C17—C16 | −175.78 (12) |
| N1—C1—C6—C5 | −178.41 (12) | N3—C16—C17—C18 | 177.42 (14) |
| C1—N1—C9—C10 | −14.2 (2) | N3—C16—C17—O2 | −7.54 (18) |
| C1—N1—C9—C14 | 169.88 (12) | O2—C17—C18—C19 | −0.22 (16) |
| N1—C9—C10—C11 | −178.26 (12) | C16—C17—C18—C19 | 175.15 (13) |
| C14—C9—C10—C11 | −2.20 (19) | C17—C18—C19—C20 | 0.08 (17) |
| C9—C10—C11—C12 | 1.3 (2) | C18—C19—C20—O2 | 0.10 (18) |
| C10—C11—C12—C13 | −0.4 (2) | C17—O2—C20—C19 | −0.23 (16) |
3-(2,3-Dimethylanilino)-N'-[(E)-(furan-2-yl)methylidene]benzohydrazide (I) . Hydrogen-bond geometry (Å, º)
Cg1 and Cg2 are the centroids of the C17–C20/O2 and C1–C6 rings, respectively.
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1···O1 | 0.910 (19) | 1.977 (18) | 2.7045 (14) | 135.8 (15) |
| N2—H2···O1i | 0.883 (18) | 2.014 (18) | 2.8458 (13) | 156.4 (15) |
| C4—H4···Cg1ii | 0.955 (17) | 2.941 (17) | 3.7248 (15) | 140.1 (17) |
| C6—H6···O1iii | 0.976 (18) | 2.556 (18) | 3.3434 (16) | 137.7 (14) |
| C11—H11···Cg2iv | 0.996 (16) | 2.765 (16) | 3.6231 (14) | 144.8 (12) |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+1, −y+1, −z+1; (iv) x, y, z+1.
N'-[(E)-Benzylidene]-2-(2,3-dimethylanilino)-benzohydrazide (II) . Crystal data
| C22H21N3O | F(000) = 728 |
| Mr = 343.42 | Dx = 1.256 Mg m−3 |
| Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
| a = 14.3493 (8) Å | Cell parameters from 9904 reflections |
| b = 15.7501 (9) Å | θ = 4.3–74.6° |
| c = 8.3737 (5) Å | µ = 0.62 mm−1 |
| β = 106.285 (2)° | T = 150 K |
| V = 1816.55 (18) Å3 | Block, pale yellow |
| Z = 4 | 0.19 × 0.13 × 0.08 mm |
N'-[(E)-Benzylidene]-2-(2,3-dimethylanilino)-benzohydrazide (II) . Data collection
| Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 3665 independent reflections |
| Radiation source: INCOATEC IµS micro–focus source | 3140 reflections with I > 2σ(I) |
| Mirror monochromator | Rint = 0.031 |
| Detector resolution: 10.4167 pixels mm-1 | θmax = 74.6°, θmin = 4.3° |
| ω scans | h = −17→16 |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | k = −19→18 |
| Tmin = 0.86, Tmax = 0.95 | l = −10→9 |
| 13875 measured reflections |
N'-[(E)-Benzylidene]-2-(2,3-dimethylanilino)-benzohydrazide (II) . Refinement
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.037 | All H-atom parameters refined |
| wR(F2) = 0.092 | w = 1/[σ2(Fo2) + (0.0409P)2 + 0.444P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.04 | (Δ/σ)max < 0.001 |
| 3665 reflections | Δρmax = 0.17 e Å−3 |
| 320 parameters | Δρmin = −0.15 e Å−3 |
| 0 restraints | Extinction correction: SHELXL 2016/6 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0033 (3) |
N'-[(E)-Benzylidene]-2-(2,3-dimethylanilino)-benzohydrazide (II) . Special details
| 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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
N'-[(E)-Benzylidene]-2-(2,3-dimethylanilino)-benzohydrazide (II) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.44514 (6) | 0.33126 (6) | 0.43024 (9) | 0.0300 (2) | |
| N1 | 0.62636 (8) | 0.39413 (8) | 0.53993 (14) | 0.0392 (3) | |
| H1 | 0.5771 (13) | 0.3712 (11) | 0.458 (2) | 0.051 (5)* | |
| N2 | 0.39227 (7) | 0.26174 (7) | 0.62519 (12) | 0.0287 (2) | |
| H2 | 0.4042 (11) | 0.2421 (10) | 0.732 (2) | 0.040 (4)* | |
| N3 | 0.30815 (7) | 0.23802 (7) | 0.50842 (12) | 0.0278 (2) | |
| C1 | 0.70441 (8) | 0.43293 (8) | 0.49433 (14) | 0.0301 (3) | |
| C2 | 0.75817 (9) | 0.38475 (8) | 0.41121 (14) | 0.0301 (3) | |
| C3 | 0.83421 (9) | 0.42441 (9) | 0.36395 (15) | 0.0330 (3) | |
| C4 | 0.85496 (10) | 0.50931 (9) | 0.40197 (17) | 0.0386 (3) | |
| H4 | 0.9098 (13) | 0.5351 (11) | 0.367 (2) | 0.052 (5)* | |
| C5 | 0.80049 (11) | 0.55653 (9) | 0.48198 (18) | 0.0411 (3) | |
| H5 | 0.8132 (13) | 0.6202 (12) | 0.504 (2) | 0.053 (5)* | |
| C6 | 0.72458 (10) | 0.51889 (9) | 0.52686 (16) | 0.0365 (3) | |
| H6 | 0.6833 (13) | 0.5527 (12) | 0.578 (2) | 0.054 (5)* | |
| C7 | 0.73544 (13) | 0.29257 (9) | 0.3725 (2) | 0.0451 (4) | |
| H7A | 0.7008 (18) | 0.2847 (16) | 0.256 (3) | 0.095 (7)* | |
| H7B | 0.7995 (19) | 0.2567 (16) | 0.388 (3) | 0.096 (8)* | |
| H7C | 0.6979 (15) | 0.2671 (13) | 0.443 (3) | 0.072 (6)* | |
| C8 | 0.89350 (12) | 0.37677 (12) | 0.2713 (2) | 0.0490 (4) | |
| H8A | 0.8504 (15) | 0.3577 (13) | 0.155 (3) | 0.068 (6)* | |
| H8B | 0.9499 (16) | 0.4120 (13) | 0.259 (2) | 0.074 (6)* | |
| H8C | 0.9197 (17) | 0.3238 (15) | 0.328 (3) | 0.083 (7)* | |
| C9 | 0.60826 (8) | 0.39908 (8) | 0.69193 (14) | 0.0300 (3) | |
| C10 | 0.67446 (9) | 0.43734 (9) | 0.83041 (16) | 0.0356 (3) | |
| H10 | 0.7358 (12) | 0.4613 (10) | 0.8156 (19) | 0.045 (4)* | |
| C11 | 0.65461 (10) | 0.44332 (9) | 0.98135 (16) | 0.0391 (3) | |
| H11 | 0.7018 (12) | 0.4732 (10) | 1.073 (2) | 0.045 (4)* | |
| C12 | 0.56938 (10) | 0.41042 (9) | 1.00387 (16) | 0.0386 (3) | |
| H12 | 0.5526 (12) | 0.4186 (11) | 1.110 (2) | 0.053 (5)* | |
| C13 | 0.50518 (9) | 0.36998 (8) | 0.87248 (15) | 0.0323 (3) | |
| H13 | 0.4448 (11) | 0.3485 (10) | 0.8855 (18) | 0.037 (4)* | |
| C14 | 0.52311 (8) | 0.36209 (8) | 0.71679 (14) | 0.0273 (3) | |
| C15 | 0.45190 (8) | 0.31809 (8) | 0.57935 (14) | 0.0259 (2) | |
| C16 | 0.25463 (8) | 0.18507 (8) | 0.55850 (14) | 0.0283 (3) | |
| H16 | 0.2745 (11) | 0.1595 (10) | 0.6724 (19) | 0.039 (4)* | |
| C17 | 0.15643 (8) | 0.16629 (8) | 0.45380 (14) | 0.0270 (2) | |
| C18 | 0.11897 (9) | 0.20627 (8) | 0.30028 (15) | 0.0325 (3) | |
| H18 | 0.1624 (12) | 0.2442 (11) | 0.258 (2) | 0.046 (4)* | |
| C19 | 0.02375 (10) | 0.19387 (9) | 0.20915 (17) | 0.0387 (3) | |
| H19 | −0.0003 (12) | 0.2241 (11) | 0.098 (2) | 0.051 (5)* | |
| C20 | −0.03663 (9) | 0.14166 (9) | 0.26957 (17) | 0.0377 (3) | |
| H20 | −0.1059 (13) | 0.1325 (11) | 0.205 (2) | 0.050 (4)* | |
| C21 | −0.00080 (9) | 0.10191 (9) | 0.42071 (17) | 0.0373 (3) | |
| H21 | −0.0449 (13) | 0.0660 (11) | 0.467 (2) | 0.051 (4)* | |
| C22 | 0.09561 (9) | 0.11354 (9) | 0.51326 (16) | 0.0333 (3) | |
| H22 | 0.1219 (11) | 0.0868 (10) | 0.6234 (19) | 0.038 (4)* |
N'-[(E)-Benzylidene]-2-(2,3-dimethylanilino)-benzohydrazide (II) . Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0270 (4) | 0.0408 (5) | 0.0213 (4) | −0.0033 (3) | 0.0051 (3) | −0.0017 (3) |
| N1 | 0.0290 (5) | 0.0598 (8) | 0.0297 (5) | −0.0158 (5) | 0.0096 (4) | −0.0104 (5) |
| N2 | 0.0229 (5) | 0.0392 (6) | 0.0212 (5) | −0.0030 (4) | 0.0019 (4) | 0.0015 (4) |
| N3 | 0.0219 (5) | 0.0362 (6) | 0.0235 (5) | −0.0016 (4) | 0.0034 (4) | −0.0018 (4) |
| C1 | 0.0235 (5) | 0.0390 (7) | 0.0261 (6) | −0.0033 (5) | 0.0041 (4) | 0.0003 (5) |
| C2 | 0.0309 (6) | 0.0328 (6) | 0.0253 (6) | −0.0003 (5) | 0.0053 (5) | 0.0017 (5) |
| C3 | 0.0282 (6) | 0.0424 (7) | 0.0281 (6) | 0.0030 (5) | 0.0076 (5) | 0.0056 (5) |
| C4 | 0.0333 (7) | 0.0454 (8) | 0.0364 (7) | −0.0080 (6) | 0.0085 (5) | 0.0067 (6) |
| C5 | 0.0463 (8) | 0.0333 (7) | 0.0417 (7) | −0.0066 (6) | 0.0092 (6) | 0.0012 (6) |
| C6 | 0.0354 (7) | 0.0362 (7) | 0.0368 (7) | 0.0037 (5) | 0.0083 (5) | −0.0027 (5) |
| C7 | 0.0632 (10) | 0.0346 (7) | 0.0402 (8) | −0.0068 (7) | 0.0189 (7) | −0.0025 (6) |
| C8 | 0.0463 (8) | 0.0616 (10) | 0.0453 (9) | 0.0114 (8) | 0.0229 (7) | 0.0053 (7) |
| C9 | 0.0248 (5) | 0.0366 (7) | 0.0263 (6) | −0.0003 (5) | 0.0034 (4) | −0.0009 (5) |
| C10 | 0.0292 (6) | 0.0416 (7) | 0.0306 (6) | −0.0046 (5) | −0.0005 (5) | −0.0013 (5) |
| C11 | 0.0416 (7) | 0.0412 (7) | 0.0268 (6) | −0.0047 (6) | −0.0030 (5) | −0.0025 (5) |
| C12 | 0.0467 (7) | 0.0436 (8) | 0.0234 (6) | −0.0018 (6) | 0.0065 (5) | −0.0032 (5) |
| C13 | 0.0336 (6) | 0.0367 (7) | 0.0260 (6) | −0.0004 (5) | 0.0074 (5) | −0.0008 (5) |
| C14 | 0.0246 (5) | 0.0329 (6) | 0.0226 (5) | 0.0012 (5) | 0.0037 (4) | −0.0007 (4) |
| C15 | 0.0205 (5) | 0.0326 (6) | 0.0237 (5) | 0.0029 (4) | 0.0050 (4) | 0.0003 (4) |
| C16 | 0.0260 (6) | 0.0352 (6) | 0.0236 (5) | 0.0009 (5) | 0.0066 (4) | 0.0004 (5) |
| C17 | 0.0251 (6) | 0.0307 (6) | 0.0252 (5) | 0.0008 (5) | 0.0070 (4) | −0.0030 (4) |
| C18 | 0.0300 (6) | 0.0369 (7) | 0.0292 (6) | 0.0000 (5) | 0.0057 (5) | 0.0012 (5) |
| C19 | 0.0330 (7) | 0.0451 (8) | 0.0326 (7) | 0.0035 (6) | 0.0001 (5) | 0.0003 (6) |
| C20 | 0.0244 (6) | 0.0447 (8) | 0.0402 (7) | 0.0007 (5) | 0.0028 (5) | −0.0106 (6) |
| C21 | 0.0298 (6) | 0.0425 (7) | 0.0411 (7) | −0.0077 (6) | 0.0123 (5) | −0.0075 (6) |
| C22 | 0.0306 (6) | 0.0381 (7) | 0.0306 (6) | −0.0049 (5) | 0.0076 (5) | −0.0009 (5) |
N'-[(E)-Benzylidene]-2-(2,3-dimethylanilino)-benzohydrazide (II) . Geometric parameters (Å, º)
| O1—C15 | 1.2424 (14) | C9—C10 | 1.4115 (17) |
| N1—C9 | 1.3707 (16) | C9—C14 | 1.4208 (17) |
| N1—C1 | 1.4189 (16) | C10—C11 | 1.3745 (19) |
| N1—H1 | 0.908 (18) | C10—H10 | 0.997 (16) |
| N2—C15 | 1.3607 (16) | C11—C12 | 1.389 (2) |
| N2—N3 | 1.3750 (13) | C11—H11 | 0.990 (16) |
| N2—H2 | 0.913 (16) | C12—C13 | 1.3770 (18) |
| N3—C16 | 1.2814 (16) | C12—H12 | 0.988 (17) |
| C1—C6 | 1.3954 (19) | C13—C14 | 1.4033 (16) |
| C1—C2 | 1.3987 (17) | C13—H13 | 0.965 (16) |
| C2—C3 | 1.4068 (17) | C14—C15 | 1.4796 (15) |
| C2—C7 | 1.5034 (19) | C16—C17 | 1.4659 (16) |
| C3—C4 | 1.387 (2) | C16—H16 | 1.000 (15) |
| C3—C8 | 1.5030 (19) | C17—C22 | 1.3941 (17) |
| C4—C5 | 1.381 (2) | C17—C18 | 1.3966 (17) |
| C4—H4 | 1.001 (17) | C18—C19 | 1.3793 (18) |
| C5—C6 | 1.382 (2) | C18—H18 | 0.997 (17) |
| C5—H5 | 1.026 (18) | C19—C20 | 1.389 (2) |
| C6—H6 | 0.980 (18) | C19—H19 | 1.013 (18) |
| C7—H7A | 0.97 (3) | C20—C21 | 1.376 (2) |
| C7—H7B | 1.06 (3) | C20—H20 | 1.000 (18) |
| C7—H7C | 0.99 (2) | C21—C22 | 1.3952 (18) |
| C8—H8A | 1.04 (2) | C21—H21 | 1.004 (18) |
| C8—H8B | 1.01 (2) | C22—H22 | 0.988 (15) |
| C8—H8C | 0.98 (2) | ||
| C9—N1—C1 | 126.50 (11) | C11—C10—C9 | 121.30 (12) |
| C9—N1—H1 | 114.2 (11) | C11—C10—H10 | 120.4 (9) |
| C1—N1—H1 | 118.4 (11) | C9—C10—H10 | 118.3 (9) |
| C15—N2—N3 | 118.21 (10) | C10—C11—C12 | 121.11 (12) |
| C15—N2—H2 | 122.4 (10) | C10—C11—H11 | 118.3 (9) |
| N3—N2—H2 | 119.3 (10) | C12—C11—H11 | 120.6 (9) |
| C16—N3—N2 | 115.55 (10) | C13—C12—C11 | 118.77 (12) |
| C6—C1—C2 | 120.68 (11) | C13—C12—H12 | 120.0 (10) |
| C6—C1—N1 | 120.10 (12) | C11—C12—H12 | 121.2 (10) |
| C2—C1—N1 | 119.17 (12) | C12—C13—C14 | 121.83 (12) |
| C1—C2—C3 | 118.60 (12) | C12—C13—H13 | 119.5 (9) |
| C1—C2—C7 | 120.96 (12) | C14—C13—H13 | 118.6 (9) |
| C3—C2—C7 | 120.44 (12) | C13—C14—C9 | 119.28 (11) |
| C4—C3—C2 | 119.79 (12) | C13—C14—C15 | 119.84 (11) |
| C4—C3—C8 | 118.91 (13) | C9—C14—C15 | 120.85 (10) |
| C2—C3—C8 | 121.30 (13) | O1—C15—N2 | 120.95 (10) |
| C5—C4—C3 | 121.08 (12) | O1—C15—C14 | 123.08 (10) |
| C5—C4—H4 | 121.5 (10) | N2—C15—C14 | 115.96 (10) |
| C3—C4—H4 | 117.4 (10) | N3—C16—C17 | 119.96 (11) |
| C4—C5—C6 | 119.84 (13) | N3—C16—H16 | 122.5 (9) |
| C4—C5—H5 | 121.3 (9) | C17—C16—H16 | 117.3 (9) |
| C6—C5—H5 | 118.8 (10) | C22—C17—C18 | 118.65 (11) |
| C5—C6—C1 | 119.96 (12) | C22—C17—C16 | 119.98 (11) |
| C5—C6—H6 | 120.4 (10) | C18—C17—C16 | 121.12 (11) |
| C1—C6—H6 | 119.6 (10) | C19—C18—C17 | 120.75 (12) |
| C2—C7—H7A | 111.1 (15) | C19—C18—H18 | 120.5 (9) |
| C2—C7—H7B | 111.2 (13) | C17—C18—H18 | 118.7 (9) |
| H7A—C7—H7B | 103.8 (19) | C18—C19—C20 | 120.31 (12) |
| C2—C7—H7C | 112.7 (12) | C18—C19—H19 | 118.0 (10) |
| H7A—C7—H7C | 109.5 (19) | C20—C19—H19 | 121.7 (10) |
| H7B—C7—H7C | 108.2 (18) | C21—C20—C19 | 119.62 (12) |
| C3—C8—H8A | 110.6 (11) | C21—C20—H20 | 119.3 (10) |
| C3—C8—H8B | 111.4 (12) | C19—C20—H20 | 121.0 (10) |
| H8A—C8—H8B | 110.3 (15) | C20—C21—C22 | 120.51 (12) |
| C3—C8—H8C | 111.8 (13) | C20—C21—H21 | 119.9 (10) |
| H8A—C8—H8C | 104.6 (17) | C22—C21—H21 | 119.6 (10) |
| H8B—C8—H8C | 107.9 (18) | C17—C22—C21 | 120.16 (12) |
| N1—C9—C10 | 121.87 (11) | C17—C22—H22 | 118.3 (9) |
| N1—C9—C14 | 120.49 (10) | C21—C22—H22 | 121.5 (9) |
| C10—C9—C14 | 117.58 (11) | ||
| C15—N2—N3—C16 | −179.78 (11) | C12—C13—C14—C9 | −2.03 (19) |
| C9—N1—C1—C6 | −49.49 (19) | C12—C13—C14—C15 | −179.98 (12) |
| C9—N1—C1—C2 | 132.87 (14) | N1—C9—C14—C13 | −178.39 (12) |
| C6—C1—C2—C3 | 1.20 (17) | C10—C9—C14—C13 | 4.26 (18) |
| N1—C1—C2—C3 | 178.83 (11) | N1—C9—C14—C15 | −0.46 (18) |
| C6—C1—C2—C7 | −178.68 (12) | C10—C9—C14—C15 | −177.81 (11) |
| N1—C1—C2—C7 | −1.05 (18) | N3—N2—C15—O1 | −18.17 (17) |
| C1—C2—C3—C4 | 0.75 (18) | N3—N2—C15—C14 | 161.30 (10) |
| C7—C2—C3—C4 | −179.36 (12) | C13—C14—C15—O1 | 156.06 (12) |
| C1—C2—C3—C8 | −178.75 (12) | C9—C14—C15—O1 | −21.86 (18) |
| C7—C2—C3—C8 | 1.13 (19) | C13—C14—C15—N2 | −23.40 (16) |
| C2—C3—C4—C5 | −1.70 (19) | C9—C14—C15—N2 | 158.68 (11) |
| C8—C3—C4—C5 | 177.82 (13) | N2—N3—C16—C17 | 169.95 (10) |
| C3—C4—C5—C6 | 0.7 (2) | N3—C16—C17—C22 | −175.28 (12) |
| C4—C5—C6—C1 | 1.3 (2) | N3—C16—C17—C18 | −1.04 (18) |
| C2—C1—C6—C5 | −2.25 (19) | C22—C17—C18—C19 | −0.02 (19) |
| N1—C1—C6—C5 | −179.86 (12) | C16—C17—C18—C19 | −174.33 (12) |
| C1—N1—C9—C10 | −7.4 (2) | C17—C18—C19—C20 | 0.4 (2) |
| C1—N1—C9—C14 | 175.32 (12) | C18—C19—C20—C21 | −0.3 (2) |
| N1—C9—C10—C11 | 178.76 (13) | C19—C20—C21—C22 | −0.1 (2) |
| C14—C9—C10—C11 | −3.9 (2) | C18—C17—C22—C21 | −0.45 (19) |
| C9—C10—C11—C12 | 1.2 (2) | C16—C17—C22—C21 | 173.93 (12) |
| C10—C11—C12—C13 | 1.2 (2) | C20—C21—C22—C17 | 0.5 (2) |
| C11—C12—C13—C14 | −0.7 (2) |
N'-[(E)-Benzylidene]-2-(2,3-dimethylanilino)-benzohydrazide (II) . Hydrogen-bond geometry (Å, º)
Cg1 and Cg3 are the centroids of the C1–C6 and C17–C22 benzene rings, respectively.
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1···O1 | 0.908 (18) | 1.946 (18) | 2.6920 (13) | 138.2 (15) |
| N2—H2···O1i | 0.913 (16) | 1.974 (17) | 2.8564 (13) | 162.0 (14) |
| C4—H4···Cg3ii | 1.001 (17) | 2.796 (17) | 3.6141 (15) | 139.4 (13) |
| C6—H6···O1iii | 0.980 (18) | 2.583 (19) | 3.4815 (16) | 152.5 (13) |
| C20—H20···Cg1iv | 1.000 (18) | 2.838 (17) | 3.6644 (15) | 140.5 (13) |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+1, −y+1, −z+1; (iv) x−1, −y−1/2, z−3/2.
Funding Statement
This work was funded by National Science Foundation grant 1228232. Tulane University grant .
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) global, I, II. DOI: 10.1107/S2056989021001353/wm5599sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989021001353/wm5599Isup2.hkl
Structure factors: contains datablock(s) II. DOI: 10.1107/S2056989021001353/wm5599IIsup3.hkl
Supporting information file. DOI: 10.1107/S2056989021001353/wm5599Isup4.cml
Supporting information file. DOI: 10.1107/S2056989021001353/wm5599IIsup5.cml
Additional supporting information: crystallographic information; 3D view; checkCIF report