organic compounds
E)-1-(2,4-dinitrophenyl)-2-[(E)-5-phenyl-1-(p-tolyl)pent-2-en-4-yn-1-ylidene]hydrazine
of (aDepartment of Chemistry Chemical Processes and Technologies, Togliatti State University, 445667 Togliatti, Russian Federation, bNesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, 119991 Moscow, Russian Federation, and cLaboratory of Functional of Heterocyclic Compounds, Togliatti State University, 445667 Togliatti, Russian Federation
*Correspondence e-mail: labofhc@gmail.com
In the title compound, C24H18N4O4, the plane of the phenyl ring is inclined to those of the toluene ring and the dinitro-substituted benzene ring by 66.96 (19) and 47.06 (18)°, respectively, while the planes of the two benzene rings are inclined to one another by 36.26 (19)°. There is an intramolecular N—H⋯O hydrogen bond between the NH group and the O atom of a nitro group, forming an S(6) ring motif. In the crystal, molecules are linked by C—H⋯O hydrogen bonds and C—H⋯π interactions, forming a three-dimensional network. There are also weak π–π interactions present involving the phenyl ring and the dinitro-substituted benzene ring [inter-centroid distance = 3.741 (2) Å].
Keywords: crystal structure; hydrazones; hydrazine; hydrogen bonding; C—H⋯π interactions; π–π interactions.
CCDC reference: 1430774
1. Related literature
For the biological activity of et al. (2005); Wu et al. (2011); Chate et al. (2012); Karaman et al. (2012). For the synthesis and of 1,5-diarylpent-2-en-4-yn-1-one precursors, see: Golovanov et al. (2013); Vologzhanina et al. (2014).
and their arylthio-containing derivatives, see: Nielsen2. Experimental
2.1. Crystal data
|
2.3. Refinement
|
Data collection: APEX2 (Bruker, 2005); cell SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2.
Supporting information
CCDC reference: 1430774
https://doi.org/10.1107/S2056989015019301/su5223sup1.cif
contains datablocks Global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015019301/su5223Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989015019301/su5223Isup3.cml
Chalcones exhibit antibiotic (Nielsen et al., 2005) and anti-inflammatory (Wu et al., 2011) activity. Arylthio-containing
are also active against some human pathogenic microorganisms (Chate et al., 2012; Karaman et al., 2012). Thus, a molecule which contains both fragments may have a high biological effect. Herein we present the synthesis and of the title hydrazone, prepared by the reaction between 2,4-dinitrophenylhydrazine and 1-(4-methylphenyl)-5-phenyl-2-penten-4-yn-1-one.In the title compound, Fig. 1, the length of the C3—C4 bond [1.427 (6) Å] indicates slight delocalization of electron density along the polyene C═ C—C═C chain. In contrast with the parent pent-2-en-4-yn-1-one compound (Vologzhanina et al., 2014) the benzene rings at C1 and C5 atoms are twisted with respect to one another, with a dihedral angle of 66.96 (19) °. There is an intramolecular N—H···O hydrogen bond, between an O atom of a nitro-group and the NH H atom forming an S(6) ring motif (Table 1 and Fig. 1).
In the crystal, molecules are linked by C—H···O hydrogen bonds and C—H···π interactions, forming a three-dimensional structure (Table 1 and Fig. 2). There are also weak π-π interactions present involving the phenyl ring and the dinitro-substituted benzene ring [Cg1···Cg3i = 3.741 (2) Å; Cg1 and Cg3 are the centroids of rings C6—C11 and C19—C24, respectively; symmetry code: x-1/2, -y+3/2, z-1/2].
A mixture of 2,4-dinitrophenylhydrazine (320 mg, 1.61 mmol), 1-(4-methylphenyl)-5-phenyl-2-penten-4-yn-1-one (374 mg, 1.61 mmol) and 1 ml concentrated HCl were dissolved in MeOH (20 ml). The reaction mixture was heated under reflux. The mixture was cooled, and the precipitate of the hydrozone was filtered off, washed on a filter with 2 ml of cold 95% EtOH, and dried (yield 87%). The single-crystals of the title compound were obtained by slow crystallization of a solution in MeOH (m.p.: 415–417 K). IR (KBr), ν/cm-1: 2196, 1615. 1H NMR (400 MHz, CDCl3): 2.44 (s, 3H), 6.43 (d, 1H, J = 16.3 Hz), 7.07 (d, 1H, J = 16.3 Hz), 7.32 (m, 5H), 7.53 (dd, 2H, J = 4.3 Hz, J = 3.0 Hz), 7.61 (d, 2H, J =8.0 Hz), 8.10 (d, 1H, J = 9.0 Hz), 8.35 (dd, 1H, J = 9.6 Hz, J = 2.0 Hz), 9.17 (d, 1H, J = 2.3 Hz), 11.65 (s, 1H). Anal. Calcd. for C24H18N4O4: C, 67.60; H, 4.26. Found: C, 67.95; H, 4.08.
Crystal data, data collection and structure
details are summarized in Table 2. The NH H atom was located in a difference Fourier map and freely refined. The C-bound H atoms were included in calculated positions and treated as riding atoms: C—H = 0.95-0.98 Å with Uiso(H) = 1.5Ueq(C-methyl) and 1.2Ueq(C) for other H atoms.Chalcones exhibit antibiotic (Nielsen et al., 2005) and anti-inflammatory (Wu et al., 2011) activity. Arylthio-containing
are also active against some human pathogenic microorganisms (Chate et al., 2012; Karaman et al., 2012). Thus, a molecule which contains both fragments may have a high biological effect. Herein we present the synthesis and of the title hydrazone, prepared by the reaction between 2,4-dinitrophenylhydrazine and 1-(4-methylphenyl)-5-phenyl-2-penten-4-yn-1-one.In the title compound, Fig. 1, the length of the C3—C4 bond [1.427 (6) Å] indicates slight delocalization of electron density along the polyene C═ C—C═C chain. In contrast with the parent pent-2-en-4-yn-1-one compound (Vologzhanina et al., 2014) the benzene rings at C1 and C5 atoms are twisted with respect to one another, with a dihedral angle of 66.96 (19) °. There is an intramolecular N—H···O hydrogen bond, between an O atom of a nitro-group and the NH H atom forming an S(6) ring motif (Table 1 and Fig. 1).
In the crystal, molecules are linked by C—H···O hydrogen bonds and C—H···π interactions, forming a three-dimensional structure (Table 1 and Fig. 2). There are also weak π-π interactions present involving the phenyl ring and the dinitro-substituted benzene ring [Cg1···Cg3i = 3.741 (2) Å; Cg1 and Cg3 are the centroids of rings C6—C11 and C19—C24, respectively; symmetry code: x-1/2, -y+3/2, z-1/2].
For the biological activity of
and their arylthio-containing derivatives, see: Nielsen et al. (2005); Wu et al. (2011); Chate et al. (2012); Karaman et al. (2012). For the synthesis and of 1,5-diarylpent-2-en-4-yn-1-one precursors, see: Golovanov et al. (2013); Vologzhanina et al. (2014).A mixture of 2,4-dinitrophenylhydrazine (320 mg, 1.61 mmol), 1-(4-methylphenyl)-5-phenyl-2-penten-4-yn-1-one (374 mg, 1.61 mmol) and 1 ml concentrated HCl were dissolved in MeOH (20 ml). The reaction mixture was heated under reflux. The mixture was cooled, and the precipitate of the hydrozone was filtered off, washed on a filter with 2 ml of cold 95% EtOH, and dried (yield 87%). The single-crystals of the title compound were obtained by slow crystallization of a solution in MeOH (m.p.: 415–417 K). IR (KBr), ν/cm-1: 2196, 1615. 1H NMR (400 MHz, CDCl3): 2.44 (s, 3H), 6.43 (d, 1H, J = 16.3 Hz), 7.07 (d, 1H, J = 16.3 Hz), 7.32 (m, 5H), 7.53 (dd, 2H, J = 4.3 Hz, J = 3.0 Hz), 7.61 (d, 2H, J =8.0 Hz), 8.10 (d, 1H, J = 9.0 Hz), 8.35 (dd, 1H, J = 9.6 Hz, J = 2.0 Hz), 9.17 (d, 1H, J = 2.3 Hz), 11.65 (s, 1H). Anal. Calcd. for C24H18N4O4: C, 67.60; H, 4.26. Found: C, 67.95; H, 4.08.
detailsCrystal data, data collection and structure
details are summarized in Table 2. The NH H atom was located in a difference Fourier map and freely refined. The C-bound H atoms were included in calculated positions and treated as riding atoms: C—H = 0.95-0.98 Å with Uiso(H) = 1.5Ueq(C-methyl) and 1.2Ueq(C) for other H atoms.Data collection: APEX2 (Bruker, 2005); cell
SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).Fig. 1. The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. | |
Fig. 2. A partial view along the b axis of the crystal packing of the title compound. The H atoms have been omitted. |
C24H18N4O4 | F(000) = 888 |
Mr = 426.42 | Dx = 1.374 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54178 Å |
a = 18.4810 (6) Å | Cell parameters from 4900 reflections |
b = 6.1674 (2) Å | θ = 2.9–66.5° |
c = 19.2366 (12) Å | µ = 0.79 mm−1 |
β = 109.902 (5)° | T = 120 K |
V = 2061.63 (17) Å3 | Needle, red |
Z = 4 | 0.42 × 0.06 × 0.06 mm |
Bruker APEXII CCD diffractometer | 3661 independent reflections |
Radiation source: fine-focus sealed tube | 2388 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.174 |
φ and ω scans | θmax = 68.1°, θmin = 2.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −22→22 |
Tmin = 0.903, Tmax = 0.916 | k = −7→7 |
27966 measured reflections | l = −21→22 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.091 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.283 | w = 1/[σ2(Fo2) + (0.1877P)2 + 0.4158P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3661 reflections | Δρmax = 0.53 e Å−3 |
295 parameters | Δρmin = −0.49 e Å−3 |
0 restraints | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0043 (10) |
C24H18N4O4 | V = 2061.63 (17) Å3 |
Mr = 426.42 | Z = 4 |
Monoclinic, P21/n | Cu Kα radiation |
a = 18.4810 (6) Å | µ = 0.79 mm−1 |
b = 6.1674 (2) Å | T = 120 K |
c = 19.2366 (12) Å | 0.42 × 0.06 × 0.06 mm |
β = 109.902 (5)° |
Bruker APEXII CCD diffractometer | 3661 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 2388 reflections with I > 2σ(I) |
Tmin = 0.903, Tmax = 0.916 | Rint = 0.174 |
27966 measured reflections |
R[F2 > 2σ(F2)] = 0.091 | 0 restraints |
wR(F2) = 0.283 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.53 e Å−3 |
3661 reflections | Δρmin = −0.49 e Å−3 |
295 parameters |
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 | 0.03666 (16) | 0.8320 (6) | 0.91286 (19) | 0.0415 (10) | |
O2 | 0.08785 (16) | 1.1218 (6) | 0.97070 (17) | 0.0347 (9) | |
O3 | 0.35551 (17) | 1.2102 (5) | 1.08437 (18) | 0.0343 (8) | |
O4 | 0.43421 (15) | 0.9726 (5) | 1.06733 (17) | 0.0337 (9) | |
N1 | 0.13617 (18) | 0.3687 (6) | 0.84326 (18) | 0.0235 (9) | |
N2 | 0.12194 (18) | 0.5366 (6) | 0.88310 (19) | 0.0239 (9) | |
H2N | 0.077 (3) | 0.598 (8) | 0.877 (3) | 0.036 (14)* | |
N3 | 0.09357 (18) | 0.9408 (6) | 0.94809 (19) | 0.0253 (9) | |
N4 | 0.36865 (19) | 1.0372 (6) | 1.05984 (19) | 0.0256 (9) | |
C1 | 0.0782 (2) | 0.2979 (7) | 0.7893 (2) | 0.0218 (10) | |
C2 | −0.0018 (2) | 0.3818 (7) | 0.7662 (2) | 0.0237 (10) | |
H2 | −0.0418 | 0.2810 | 0.7626 | 0.028* | |
C3 | −0.0214 (2) | 0.5874 (7) | 0.7502 (2) | 0.0239 (10) | |
H3 | 0.0183 | 0.6913 | 0.7564 | 0.029* | |
C4 | −0.0994 (2) | 0.6596 (8) | 0.7240 (2) | 0.0267 (10) | |
C5 | −0.1651 (2) | 0.7169 (8) | 0.7004 (2) | 0.0261 (10) | |
C6 | −0.2456 (2) | 0.7682 (7) | 0.6685 (2) | 0.0229 (10) | |
C7 | −0.3002 (2) | 0.6081 (8) | 0.6657 (2) | 0.0278 (11) | |
H7 | −0.2841 | 0.4694 | 0.6868 | 0.033* | |
C8 | −0.3780 (2) | 0.6527 (8) | 0.6322 (2) | 0.0307 (11) | |
H8 | −0.4150 | 0.5436 | 0.6301 | 0.037* | |
C9 | −0.4020 (2) | 0.8530 (8) | 0.6020 (2) | 0.0293 (11) | |
H9 | −0.4553 | 0.8816 | 0.5785 | 0.035* | |
C10 | −0.3485 (2) | 1.0128 (8) | 0.6058 (2) | 0.0292 (11) | |
H10 | −0.3650 | 1.1522 | 0.5857 | 0.035* | |
C11 | −0.2702 (2) | 0.9698 (7) | 0.6390 (2) | 0.0268 (10) | |
H11 | −0.2336 | 1.0802 | 0.6414 | 0.032* | |
C12 | 0.0927 (2) | 0.1107 (7) | 0.7471 (2) | 0.0210 (9) | |
C13 | 0.0446 (2) | 0.0721 (7) | 0.6754 (2) | 0.0260 (10) | |
H13 | 0.0018 | 0.1644 | 0.6534 | 0.031* | |
C14 | 0.0585 (2) | −0.1003 (7) | 0.6353 (2) | 0.0275 (11) | |
H14 | 0.0253 | −0.1240 | 0.5859 | 0.033* | |
C15 | 0.1208 (2) | −0.2392 (7) | 0.6668 (2) | 0.0245 (10) | |
C16 | 0.1688 (2) | −0.2011 (7) | 0.7387 (2) | 0.0261 (10) | |
H16 | 0.2108 | −0.2960 | 0.7611 | 0.031* | |
C17 | 0.1563 (2) | −0.0273 (7) | 0.7783 (2) | 0.0251 (10) | |
H17 | 0.1908 | −0.0003 | 0.8269 | 0.030* | |
C18 | 0.1338 (2) | −0.4305 (8) | 0.6238 (3) | 0.0331 (12) | |
H18C | 0.1508 | −0.5552 | 0.6569 | 0.050* | |
H18B | 0.1733 | −0.3941 | 0.6023 | 0.050* | |
H18A | 0.0856 | −0.4667 | 0.5841 | 0.050* | |
C19 | 0.1805 (2) | 0.6534 (7) | 0.9298 (2) | 0.0218 (10) | |
C20 | 0.1700 (2) | 0.8485 (7) | 0.9621 (2) | 0.0207 (9) | |
C21 | 0.2312 (2) | 0.9736 (7) | 1.0058 (2) | 0.0216 (10) | |
H21 | 0.2226 | 1.1075 | 1.0261 | 0.026* | |
C22 | 0.3048 (2) | 0.8976 (7) | 1.0187 (2) | 0.0221 (10) | |
C23 | 0.3174 (2) | 0.7040 (8) | 0.9893 (2) | 0.0251 (10) | |
H23 | 0.3687 | 0.6549 | 0.9996 | 0.030* | |
C24 | 0.2583 (2) | 0.5810 (7) | 0.9458 (2) | 0.0261 (10) | |
H24 | 0.2685 | 0.4476 | 0.9261 | 0.031* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0141 (15) | 0.054 (2) | 0.049 (2) | 0.0019 (15) | 0.0020 (14) | −0.0209 (18) |
O2 | 0.0210 (15) | 0.045 (2) | 0.0337 (19) | 0.0090 (14) | 0.0032 (13) | −0.0054 (16) |
O3 | 0.0243 (16) | 0.036 (2) | 0.0363 (19) | −0.0025 (14) | 0.0024 (13) | −0.0077 (15) |
O4 | 0.0146 (14) | 0.048 (2) | 0.0335 (18) | 0.0014 (14) | 0.0018 (12) | −0.0048 (15) |
N1 | 0.0194 (17) | 0.030 (2) | 0.0198 (18) | 0.0003 (15) | 0.0045 (14) | −0.0016 (15) |
N2 | 0.0113 (16) | 0.036 (2) | 0.0210 (19) | 0.0008 (15) | 0.0010 (14) | −0.0081 (16) |
N3 | 0.0165 (17) | 0.034 (2) | 0.0212 (19) | 0.0048 (16) | 0.0011 (14) | −0.0079 (16) |
N4 | 0.0204 (18) | 0.033 (2) | 0.0205 (19) | −0.0014 (16) | 0.0033 (14) | 0.0011 (16) |
C1 | 0.0145 (19) | 0.031 (3) | 0.019 (2) | 0.0018 (17) | 0.0055 (16) | 0.0040 (17) |
C2 | 0.0153 (19) | 0.032 (3) | 0.023 (2) | 0.0005 (18) | 0.0053 (16) | 0.0000 (19) |
C3 | 0.0149 (19) | 0.036 (3) | 0.017 (2) | 0.0038 (18) | 0.0001 (15) | 0.0029 (18) |
C4 | 0.022 (2) | 0.036 (3) | 0.020 (2) | 0.0042 (19) | 0.0058 (17) | 0.0005 (19) |
C5 | 0.021 (2) | 0.037 (3) | 0.016 (2) | 0.0047 (19) | −0.0004 (16) | 0.0026 (18) |
C6 | 0.0140 (18) | 0.033 (3) | 0.019 (2) | 0.0037 (17) | 0.0017 (15) | 0.0028 (18) |
C7 | 0.027 (2) | 0.036 (3) | 0.019 (2) | 0.001 (2) | 0.0067 (18) | 0.0023 (19) |
C8 | 0.019 (2) | 0.045 (3) | 0.029 (2) | −0.005 (2) | 0.0081 (18) | −0.002 (2) |
C9 | 0.016 (2) | 0.046 (3) | 0.024 (2) | 0.001 (2) | 0.0044 (17) | −0.004 (2) |
C10 | 0.022 (2) | 0.039 (3) | 0.023 (2) | 0.010 (2) | 0.0021 (17) | 0.007 (2) |
C11 | 0.021 (2) | 0.031 (3) | 0.025 (2) | 0.0005 (19) | 0.0038 (17) | 0.0026 (18) |
C12 | 0.0152 (18) | 0.030 (3) | 0.017 (2) | 0.0005 (17) | 0.0045 (15) | 0.0024 (17) |
C13 | 0.019 (2) | 0.032 (3) | 0.021 (2) | 0.0030 (18) | −0.0013 (17) | 0.0017 (19) |
C14 | 0.022 (2) | 0.035 (3) | 0.020 (2) | −0.0017 (19) | 0.0011 (17) | −0.0041 (19) |
C15 | 0.021 (2) | 0.027 (3) | 0.027 (2) | −0.0035 (18) | 0.0115 (17) | −0.0019 (18) |
C16 | 0.0173 (19) | 0.033 (3) | 0.025 (2) | 0.0044 (18) | 0.0032 (17) | 0.0001 (19) |
C17 | 0.0133 (19) | 0.037 (3) | 0.021 (2) | −0.0007 (18) | 0.0008 (16) | 0.0014 (19) |
C18 | 0.023 (2) | 0.045 (3) | 0.031 (3) | −0.001 (2) | 0.0092 (19) | −0.010 (2) |
C19 | 0.017 (2) | 0.031 (3) | 0.016 (2) | 0.0003 (17) | 0.0042 (16) | 0.0017 (17) |
C20 | 0.0126 (19) | 0.028 (3) | 0.018 (2) | 0.0026 (16) | 0.0005 (15) | 0.0028 (17) |
C21 | 0.023 (2) | 0.029 (3) | 0.0111 (19) | 0.0003 (18) | 0.0024 (15) | 0.0005 (17) |
C22 | 0.0154 (19) | 0.033 (3) | 0.014 (2) | −0.0037 (18) | 0.0002 (15) | 0.0028 (17) |
C23 | 0.0135 (19) | 0.037 (3) | 0.023 (2) | 0.0015 (18) | 0.0034 (16) | 0.0007 (19) |
C24 | 0.017 (2) | 0.033 (3) | 0.025 (2) | 0.0033 (18) | 0.0033 (17) | 0.0020 (19) |
O1—N3 | 1.237 (4) | C10—C11 | 1.394 (6) |
O2—N3 | 1.215 (4) | C10—H10 | 0.9500 |
O3—N4 | 1.224 (5) | C11—H11 | 0.9500 |
O4—N4 | 1.236 (4) | C12—C13 | 1.383 (6) |
N1—C1 | 1.288 (5) | C12—C17 | 1.409 (6) |
N1—N2 | 1.366 (5) | C13—C14 | 1.388 (6) |
N2—C19 | 1.355 (5) | C13—H13 | 0.9500 |
N2—H2N | 0.89 (5) | C14—C15 | 1.396 (6) |
N3—C20 | 1.461 (5) | C14—H14 | 0.9500 |
N4—C22 | 1.457 (5) | C15—C16 | 1.387 (6) |
C1—C2 | 1.484 (5) | C15—C18 | 1.507 (6) |
C1—C12 | 1.488 (6) | C16—C17 | 1.378 (6) |
C2—C3 | 1.326 (6) | C16—H16 | 0.9500 |
C2—H2 | 0.9500 | C17—H17 | 0.9500 |
C3—C4 | 1.427 (6) | C18—H18C | 0.9800 |
C3—H3 | 0.9500 | C18—H18B | 0.9800 |
C4—C5 | 1.195 (6) | C18—H18A | 0.9800 |
C5—C6 | 1.439 (5) | C19—C20 | 1.398 (6) |
C6—C11 | 1.377 (6) | C19—C24 | 1.435 (5) |
C6—C7 | 1.400 (6) | C20—C21 | 1.391 (6) |
C7—C8 | 1.388 (6) | C21—C22 | 1.379 (6) |
C7—H7 | 0.9500 | C21—H21 | 0.9500 |
C8—C9 | 1.373 (7) | C22—C23 | 1.374 (6) |
C8—H8 | 0.9500 | C23—C24 | 1.358 (6) |
C9—C10 | 1.380 (6) | C23—H23 | 0.9500 |
C9—H9 | 0.9500 | C24—H24 | 0.9500 |
C1—N1—N2 | 116.2 (3) | C17—C12—C1 | 121.0 (4) |
C19—N2—N1 | 120.8 (3) | C12—C13—C14 | 120.6 (4) |
C19—N2—H2N | 112 (3) | C12—C13—H13 | 119.7 |
N1—N2—H2N | 127 (3) | C14—C13—H13 | 119.7 |
O2—N3—O1 | 122.2 (3) | C13—C14—C15 | 120.6 (4) |
O2—N3—C20 | 119.2 (3) | C13—C14—H14 | 119.7 |
O1—N3—C20 | 118.6 (4) | C15—C14—H14 | 119.7 |
O3—N4—O4 | 123.4 (4) | C16—C15—C14 | 118.8 (4) |
O3—N4—C22 | 119.6 (3) | C16—C15—C18 | 120.9 (4) |
O4—N4—C22 | 116.9 (4) | C14—C15—C18 | 120.3 (4) |
N1—C1—C2 | 126.5 (4) | C17—C16—C15 | 120.8 (4) |
N1—C1—C12 | 116.6 (3) | C17—C16—H16 | 119.6 |
C2—C1—C12 | 117.0 (3) | C15—C16—H16 | 119.6 |
C3—C2—C1 | 124.6 (4) | C16—C17—C12 | 120.4 (4) |
C3—C2—H2 | 117.7 | C16—C17—H17 | 119.8 |
C1—C2—H2 | 117.7 | C12—C17—H17 | 119.8 |
C2—C3—C4 | 122.9 (4) | C15—C18—H18C | 109.5 |
C2—C3—H3 | 118.5 | C15—C18—H18B | 109.5 |
C4—C3—H3 | 118.5 | H18C—C18—H18B | 109.5 |
C5—C4—C3 | 178.3 (5) | C15—C18—H18A | 109.5 |
C4—C5—C6 | 174.9 (5) | H18C—C18—H18A | 109.5 |
C11—C6—C7 | 119.2 (4) | H18B—C18—H18A | 109.5 |
C11—C6—C5 | 121.5 (4) | N2—C19—C20 | 123.5 (4) |
C7—C6—C5 | 119.3 (4) | N2—C19—C24 | 119.6 (4) |
C8—C7—C6 | 119.8 (4) | C20—C19—C24 | 116.9 (4) |
C8—C7—H7 | 120.1 | C21—C20—C19 | 122.6 (4) |
C6—C7—H7 | 120.1 | C21—C20—N3 | 115.6 (4) |
C9—C8—C7 | 120.6 (4) | C19—C20—N3 | 121.7 (3) |
C9—C8—H8 | 119.7 | C22—C21—C20 | 118.0 (4) |
C7—C8—H8 | 119.7 | C22—C21—H21 | 121.0 |
C8—C9—C10 | 119.9 (4) | C20—C21—H21 | 121.0 |
C8—C9—H9 | 120.1 | C23—C22—C21 | 121.0 (4) |
C10—C9—H9 | 120.1 | C23—C22—N4 | 121.2 (4) |
C9—C10—C11 | 120.1 (4) | C21—C22—N4 | 117.6 (4) |
C9—C10—H10 | 120.0 | C24—C23—C22 | 121.7 (4) |
C11—C10—H10 | 120.0 | C24—C23—H23 | 119.1 |
C6—C11—C10 | 120.4 (4) | C22—C23—H23 | 119.1 |
C6—C11—H11 | 119.8 | C23—C24—C19 | 119.6 (4) |
C10—C11—H11 | 119.8 | C23—C24—H24 | 120.2 |
C13—C12—C17 | 118.7 (4) | C19—C24—H24 | 120.2 |
C13—C12—C1 | 120.2 (4) | ||
C1—N1—N2—C19 | −165.5 (4) | C13—C12—C17—C16 | −2.0 (6) |
N2—N1—C1—C2 | 0.5 (6) | C1—C12—C17—C16 | 179.5 (4) |
N2—N1—C1—C12 | −178.2 (3) | N1—N2—C19—C20 | 168.5 (4) |
N1—C1—C2—C3 | 54.1 (6) | N1—N2—C19—C24 | −9.2 (6) |
C12—C1—C2—C3 | −127.2 (5) | N2—C19—C20—C21 | −175.4 (4) |
C1—C2—C3—C4 | 176.3 (4) | C24—C19—C20—C21 | 2.4 (6) |
C11—C6—C7—C8 | 1.3 (6) | N2—C19—C20—N3 | 0.5 (6) |
C5—C6—C7—C8 | −177.2 (4) | C24—C19—C20—N3 | 178.3 (4) |
C6—C7—C8—C9 | −0.4 (7) | O2—N3—C20—C21 | 4.4 (6) |
C7—C8—C9—C10 | −0.9 (7) | O1—N3—C20—C21 | −176.3 (4) |
C8—C9—C10—C11 | 1.1 (7) | O2—N3—C20—C19 | −171.9 (4) |
C7—C6—C11—C10 | −1.1 (6) | O1—N3—C20—C19 | 7.5 (6) |
C5—C6—C11—C10 | 177.4 (4) | C19—C20—C21—C22 | −1.6 (6) |
C9—C10—C11—C6 | −0.1 (7) | N3—C20—C21—C22 | −177.8 (3) |
N1—C1—C12—C13 | −157.2 (4) | C20—C21—C22—C23 | 0.0 (6) |
C2—C1—C12—C13 | 24.0 (6) | C20—C21—C22—N4 | 175.5 (3) |
N1—C1—C12—C17 | 21.3 (6) | O3—N4—C22—C23 | 178.9 (4) |
C2—C1—C12—C17 | −157.5 (4) | O4—N4—C22—C23 | −0.4 (6) |
C17—C12—C13—C14 | 0.5 (6) | O3—N4—C22—C21 | 3.4 (6) |
C1—C12—C13—C14 | 179.0 (4) | O4—N4—C22—C21 | −175.9 (4) |
C12—C13—C14—C15 | 0.7 (7) | C21—C22—C23—C24 | 0.8 (7) |
C13—C14—C15—C16 | −0.4 (6) | N4—C22—C23—C24 | −174.6 (4) |
C13—C14—C15—C18 | 177.8 (4) | C22—C23—C24—C19 | 0.0 (7) |
C14—C15—C16—C17 | −1.1 (6) | N2—C19—C24—C23 | 176.4 (4) |
C18—C15—C16—C17 | −179.3 (4) | C20—C19—C24—C23 | −1.5 (6) |
C15—C16—C17—C12 | 2.3 (7) |
Cg2 is the centroid of the C12–C17 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···O1 | 0.89 (5) | 1.86 (5) | 2.597 (5) | 139 (4) |
C8—H8···O1i | 0.95 | 2.49 | 3.396 (5) | 160 |
C10—H10···O2ii | 0.95 | 2.51 | 3.337 (5) | 146 |
C3—H3···Cg2iii | 0.95 | 2.63 | 3.504 (4) | 153 |
Symmetry codes: (i) −x−1/2, y−1/2, −z+3/2; (ii) x−1/2, −y+5/2, z−1/2; (iii) x, y+1, z. |
Cg2 is the centroid of the C12–C17 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···O1 | 0.89 (5) | 1.86 (5) | 2.597 (5) | 139 (4) |
C8—H8···O1i | 0.95 | 2.49 | 3.396 (5) | 160 |
C10—H10···O2ii | 0.95 | 2.51 | 3.337 (5) | 146 |
C3—H3···Cg2iii | 0.95 | 2.63 | 3.504 (4) | 153 |
Symmetry codes: (i) −x−1/2, y−1/2, −z+3/2; (ii) x−1/2, −y+5/2, z−1/2; (iii) x, y+1, z. |
Acknowledgements
The authors are grateful to the Ministry of Education and Science of the Russian Federation for supporting this work (State program No. 426).
References
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chate, A. V., Joshi, R. S., Mandhane, P. G., Mohekar, S. R. & Gill, C. H. (2012). Phosphorus Sulfur Silicon Relat. Elem. 187, 327–335. Web of Science CrossRef CAS Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Golovanov, A. A., Latypova, D. R., Bekin, V. V., Pisareva, V. S., Vologzhanina, A. V. & Dokichev, V. A. (2013). Russ. J. Org. Chem. 49, 1264–1269. Web of Science CrossRef CAS Google Scholar
Karaman, İ, Gezegen, H., Ceylan, M. & Dilmaç, M. (2012). Phosphorus Sulfur Silicon Relat. Elem. 187, 580–586. Web of Science CrossRef CAS Google Scholar
Nielsen, S. F., Larsen, M., Boesen, T., Schønning, K. & Kromann, H. (2005). J. Med. Chem. 48, 2667–2677. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Vologzhanina, A. V., Golovanov, A. A., Gusev, D. M., Odin, S. I., Apreyan, R. A. & Suponitsky, K. Yu. (2014). Cryst. Growth Des. 14, 4402–4410. Web of Science CSD CrossRef CAS Google Scholar
Wu, J., Li, J., Cai, Y., Pan, Y., Ye, F., Zhang, Y., Zhao, Y., Yang, S., Li, X. & Liang, G. (2011). J. Med. Chem. 54, 8110–8123. Web of Science CrossRef CAS PubMed Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.