organic compounds
4-{[2-(2,4-Dinitrophenyl)hydrazinylidene](phenyl)methyl}-5-methyl-2-phenyl-1H-pyrazol-3(2H)-one ethanol monosolvate
aUniversity of Fort Hare, Department of Chemistry, Private Bag X1314, Alice 5700, South Africa, and bNelson Mandela Metropolitan University, Department of Chemistry, PO Box 77000, Port Elizabeth 6031, South Africa
*Correspondence e-mail: idemudiaog@yahoo.com
In the title compound, C23H18N6O5·C2H6O, all three benzene rings lie in an approximate plane [maximum deviation = 0.2688 (16) Å] that makes an angle of 53.56 (3)° with the plane of the pyrazolone ring. Intramolecular N—H⋯O hydrogen bonds occur. In the crystal, the ethanol solvent molecule links adjacent molecules through N—H⋯O—H⋯O hydrogen bonds, leading to an infinite chain along the c-axis direction. The ethyl group of the ethanol solvent molecule is disordered over two set of sites in a 0.762 (5):0.238 (5) ratio.
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2010); cell SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and SHELXLE (Hübschle et al., 2011); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).
Supporting information
10.1107/S1600536812044935/ng5294sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812044935/ng5294Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812044935/ng5294Isup3.cdx
Supporting information file. DOI: 10.1107/S1600536812044935/ng5294Isup4.cml
An equimolar mixture of 2,4-dinitrophenyl hydrazine and 4-benzoyl-3-methyl-1-phenyl-2-pyrazoline-5-one in ethanol stirred under reflux for 4 h, afforded a precipitate of the titled compound. Slow evaporation at room temperature of an ethanolic solution of it, gave red single crystals suitable for X-ray diffraction with a melting point of 233–236 °C after a few days.
Carbon bound H atoms were placed in calculated positions and refined as riding atoms, with C—H = 0.95 Å (aromatic CH), 0.99 Å (CH2), 0.98 Å (CH3) and with Uiso(H) = 1.2 (1.5 for methyl) Ueq(C). The nitrogen and oxygen bound H atoms were located on a difference Fourier map and allowed to refine freely. The reflections 011 and 100 were omitted from the
since they were obscured by the beam-stop.Data collection: APEX2 (Bruker, 2010); cell
SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and SHELXLE (Hübschle et al., 2011); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).C23H18N6O5·C2H6O | Dx = 1.358 Mg m−3 |
Mr = 504.50 | Melting point: 507 K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.8289 (4) Å | Cell parameters from 94 reflections |
b = 14.3247 (4) Å | θ = 2.9–28.9° |
c = 14.4213 (4) Å | µ = 0.10 mm−1 |
β = 111.347 (1)° | T = 200 K |
V = 2468.38 (12) Å3 | Block, red |
Z = 4 | 0.61 × 0.43 × 0.39 mm |
F(000) = 1056 |
Bruker APEXII CCD diffractometer | 6124 independent reflections |
Graphite monochromator | 5136 reflections with I > 2σ(I) |
Detector resolution: 8.3333 pixels mm-1 | Rint = 0.014 |
ϕ and ω scans | θmax = 28.3°, θmin = 2.2° |
Absorption correction: numerical (SADABS; Bruker, 2008) | h = −16→17 |
Tmin = 0.89, Tmax = 0.96 | k = −13→19 |
23873 measured reflections | l = −19→19 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.116 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0507P)2 + 0.8241P] where P = (Fo2 + 2Fc2)/3 |
6124 reflections | (Δ/σ)max < 0.001 |
368 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
C23H18N6O5·C2H6O | V = 2468.38 (12) Å3 |
Mr = 504.50 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.8289 (4) Å | µ = 0.10 mm−1 |
b = 14.3247 (4) Å | T = 200 K |
c = 14.4213 (4) Å | 0.61 × 0.43 × 0.39 mm |
β = 111.347 (1)° |
Bruker APEXII CCD diffractometer | 6124 independent reflections |
Absorption correction: numerical (SADABS; Bruker, 2008) | 5136 reflections with I > 2σ(I) |
Tmin = 0.89, Tmax = 0.96 | Rint = 0.014 |
23873 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.116 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.28 e Å−3 |
6124 reflections | Δρmin = −0.22 e Å−3 |
368 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.14776 (8) | 0.69594 (6) | 0.47229 (6) | 0.0383 (2) | |
O2 | −0.07049 (9) | 0.77842 (7) | 0.42852 (9) | 0.0543 (3) | |
O3 | −0.22537 (11) | 0.83873 (7) | 0.42516 (10) | 0.0588 (3) | |
O4 | −0.53149 (10) | 0.65498 (10) | 0.42226 (12) | 0.0730 (4) | |
O5 | −0.53782 (10) | 0.50904 (11) | 0.38432 (14) | 0.0876 (5) | |
O6 | 0.30397 (9) | 0.73560 (9) | 0.64059 (8) | 0.0517 (3) | |
N1 | 0.20431 (9) | 0.73686 (7) | 0.34187 (7) | 0.0317 (2) | |
N2 | 0.20240 (9) | 0.69518 (7) | 0.25557 (8) | 0.0341 (2) | |
N3 | −0.01147 (8) | 0.51321 (7) | 0.38324 (8) | 0.0325 (2) | |
N4 | −0.05711 (9) | 0.59824 (7) | 0.39281 (8) | 0.0328 (2) | |
N5 | −0.16820 (10) | 0.77102 (7) | 0.42199 (8) | 0.0399 (2) | |
N6 | −0.48924 (10) | 0.58418 (10) | 0.40330 (11) | 0.0553 (3) | |
C1 | 0.15772 (9) | 0.67707 (8) | 0.39078 (8) | 0.0299 (2) | |
C2 | 0.12604 (9) | 0.59567 (8) | 0.33014 (8) | 0.0294 (2) | |
C3 | 0.15677 (10) | 0.61039 (8) | 0.24838 (9) | 0.0321 (2) | |
C4 | 0.14119 (14) | 0.55220 (10) | 0.15841 (10) | 0.0466 (3) | |
H4A | 0.1162 | 0.5919 | 0.099 | 0.07* | |
H4B | 0.0848 | 0.504 | 0.1522 | 0.07* | |
H4C | 0.2123 | 0.5225 | 0.1649 | 0.07* | |
C5 | 0.07256 (9) | 0.51282 (8) | 0.35381 (8) | 0.0292 (2) | |
C11 | 0.24261 (10) | 0.82994 (8) | 0.36714 (9) | 0.0322 (2) | |
C12 | 0.17815 (12) | 0.89102 (9) | 0.39821 (11) | 0.0424 (3) | |
H12 | 0.1083 | 0.8716 | 0.4005 | 0.051* | |
C13 | 0.21730 (15) | 0.98106 (10) | 0.42595 (12) | 0.0514 (4) | |
H13 | 0.1746 | 1.0234 | 0.4484 | 0.062* | |
C14 | 0.31808 (15) | 1.00912 (10) | 0.42101 (12) | 0.0532 (4) | |
H14 | 0.3447 | 1.0706 | 0.4406 | 0.064* | |
C15 | 0.38033 (14) | 0.94861 (11) | 0.38782 (12) | 0.0520 (4) | |
H15 | 0.4485 | 0.9691 | 0.3828 | 0.062* | |
C16 | 0.34373 (11) | 0.85755 (9) | 0.36157 (10) | 0.0410 (3) | |
H16 | 0.3873 | 0.8151 | 0.3402 | 0.049* | |
C21 | 0.11659 (10) | 0.41870 (8) | 0.34431 (8) | 0.0304 (2) | |
C22 | 0.05139 (11) | 0.33871 (9) | 0.33661 (10) | 0.0375 (3) | |
H22 | −0.0221 | 0.3442 | 0.3374 | 0.045* | |
C23 | 0.09362 (13) | 0.25170 (9) | 0.32782 (11) | 0.0453 (3) | |
H23 | 0.0489 | 0.1977 | 0.3227 | 0.054* | |
C24 | 0.20034 (13) | 0.24258 (10) | 0.32641 (10) | 0.0461 (3) | |
H24 | 0.2282 | 0.1827 | 0.3189 | 0.055* | |
C25 | 0.26619 (12) | 0.32073 (10) | 0.33591 (11) | 0.0455 (3) | |
H25 | 0.34 | 0.3147 | 0.3361 | 0.055* | |
C26 | 0.22459 (11) | 0.40835 (9) | 0.34526 (10) | 0.0379 (3) | |
H26 | 0.2706 | 0.4618 | 0.3524 | 0.045* | |
C31 | −0.16063 (10) | 0.59744 (8) | 0.39772 (8) | 0.0302 (2) | |
C32 | −0.21772 (10) | 0.67863 (8) | 0.41052 (9) | 0.0322 (2) | |
C33 | −0.32476 (11) | 0.67409 (9) | 0.41267 (9) | 0.0364 (3) | |
H33 | −0.3614 | 0.7291 | 0.4215 | 0.044* | |
C34 | −0.37698 (10) | 0.58920 (10) | 0.40188 (10) | 0.0393 (3) | |
C35 | −0.32465 (11) | 0.50752 (10) | 0.38895 (11) | 0.0422 (3) | |
H35 | −0.3622 | 0.4493 | 0.3817 | 0.051* | |
C36 | −0.21948 (11) | 0.51165 (9) | 0.38672 (10) | 0.0378 (3) | |
H36 | −0.1846 | 0.4557 | 0.3776 | 0.045* | |
H2N | 0.2371 (14) | 0.7212 (12) | 0.2146 (13) | 0.054 (5)* | |
H4N | −0.0119 (14) | 0.6495 (12) | 0.4120 (12) | 0.050 (4)* | |
H6 | 0.2561 (18) | 0.7277 (14) | 0.5787 (17) | 0.072 (6)* | |
C6A | 0.41626 (18) | 0.74427 (15) | 0.64338 (17) | 0.0497 (6) | 0.762 (5) |
H6AA | 0.4222 | 0.7136 | 0.584 | 0.06* | 0.762 (5) |
H6AB | 0.4678 | 0.7119 | 0.7031 | 0.06* | 0.762 (5) |
C7A | 0.4500 (3) | 0.8432 (2) | 0.64576 (19) | 0.0669 (9) | 0.762 (5) |
H7AA | 0.4044 | 0.8737 | 0.5833 | 0.1* | 0.762 (5) |
H7AB | 0.5292 | 0.8467 | 0.6539 | 0.1* | 0.762 (5) |
H7AC | 0.4389 | 0.8749 | 0.7017 | 0.1* | 0.762 (5) |
C6B | 0.3762 (6) | 0.8194 (5) | 0.6360 (5) | 0.053 (2) | 0.238 (5) |
H6BA | 0.3433 | 0.8529 | 0.5719 | 0.064* | 0.238 (5) |
H6BB | 0.3852 | 0.8636 | 0.6913 | 0.064* | 0.238 (5) |
C7B | 0.4832 (8) | 0.7761 (8) | 0.6459 (10) | 0.091 (4) | 0.238 (5) |
H7BA | 0.4727 | 0.7356 | 0.5885 | 0.136* | 0.238 (5) |
H7BB | 0.5105 | 0.7389 | 0.7071 | 0.136* | 0.238 (5) |
H7BC | 0.5379 | 0.8248 | 0.6488 | 0.136* | 0.238 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0441 (5) | 0.0430 (5) | 0.0328 (4) | −0.0148 (4) | 0.0199 (4) | −0.0091 (4) |
O2 | 0.0559 (6) | 0.0345 (5) | 0.0824 (8) | −0.0116 (4) | 0.0368 (6) | −0.0076 (5) |
O3 | 0.0760 (8) | 0.0300 (5) | 0.0843 (8) | 0.0055 (5) | 0.0457 (7) | −0.0046 (5) |
O4 | 0.0488 (6) | 0.0734 (8) | 0.1089 (11) | 0.0175 (6) | 0.0432 (7) | 0.0078 (8) |
O5 | 0.0437 (7) | 0.0796 (10) | 0.1479 (15) | −0.0183 (6) | 0.0448 (8) | −0.0171 (9) |
O6 | 0.0405 (5) | 0.0805 (8) | 0.0385 (5) | −0.0101 (5) | 0.0197 (4) | −0.0182 (5) |
N1 | 0.0401 (5) | 0.0269 (5) | 0.0327 (5) | −0.0068 (4) | 0.0186 (4) | −0.0038 (4) |
N2 | 0.0466 (6) | 0.0290 (5) | 0.0335 (5) | −0.0046 (4) | 0.0229 (4) | −0.0024 (4) |
N3 | 0.0329 (5) | 0.0267 (5) | 0.0399 (5) | −0.0011 (4) | 0.0154 (4) | −0.0001 (4) |
N4 | 0.0347 (5) | 0.0252 (5) | 0.0423 (5) | −0.0032 (4) | 0.0185 (4) | −0.0012 (4) |
N5 | 0.0526 (7) | 0.0289 (5) | 0.0443 (6) | −0.0025 (5) | 0.0249 (5) | −0.0027 (4) |
N6 | 0.0333 (6) | 0.0630 (9) | 0.0725 (9) | 0.0017 (6) | 0.0227 (6) | 0.0030 (7) |
C1 | 0.0308 (5) | 0.0297 (5) | 0.0305 (5) | −0.0050 (4) | 0.0129 (4) | −0.0017 (4) |
C2 | 0.0323 (5) | 0.0259 (5) | 0.0314 (5) | −0.0024 (4) | 0.0134 (4) | −0.0012 (4) |
C3 | 0.0383 (6) | 0.0267 (5) | 0.0338 (6) | −0.0006 (4) | 0.0162 (5) | −0.0015 (4) |
C4 | 0.0689 (9) | 0.0375 (7) | 0.0414 (7) | −0.0057 (6) | 0.0297 (7) | −0.0093 (5) |
C5 | 0.0296 (5) | 0.0269 (5) | 0.0302 (5) | −0.0041 (4) | 0.0098 (4) | −0.0006 (4) |
C11 | 0.0394 (6) | 0.0254 (5) | 0.0311 (5) | −0.0054 (4) | 0.0119 (5) | −0.0003 (4) |
C12 | 0.0466 (7) | 0.0338 (6) | 0.0478 (7) | −0.0022 (5) | 0.0182 (6) | −0.0054 (5) |
C13 | 0.0679 (10) | 0.0303 (7) | 0.0527 (8) | 0.0016 (6) | 0.0181 (7) | −0.0058 (6) |
C14 | 0.0717 (10) | 0.0267 (6) | 0.0499 (8) | −0.0124 (6) | 0.0089 (7) | 0.0011 (6) |
C15 | 0.0540 (8) | 0.0406 (8) | 0.0571 (9) | −0.0187 (7) | 0.0151 (7) | 0.0049 (6) |
C16 | 0.0425 (7) | 0.0354 (6) | 0.0466 (7) | −0.0072 (5) | 0.0181 (6) | 0.0018 (5) |
C21 | 0.0328 (6) | 0.0273 (5) | 0.0298 (5) | −0.0020 (4) | 0.0098 (4) | −0.0001 (4) |
C22 | 0.0366 (6) | 0.0318 (6) | 0.0414 (6) | −0.0067 (5) | 0.0108 (5) | −0.0041 (5) |
C23 | 0.0542 (8) | 0.0294 (6) | 0.0461 (7) | −0.0078 (6) | 0.0110 (6) | −0.0064 (5) |
C24 | 0.0596 (9) | 0.0319 (6) | 0.0423 (7) | 0.0098 (6) | 0.0132 (6) | −0.0015 (5) |
C25 | 0.0431 (7) | 0.0435 (7) | 0.0509 (8) | 0.0108 (6) | 0.0184 (6) | 0.0043 (6) |
C26 | 0.0348 (6) | 0.0330 (6) | 0.0465 (7) | −0.0002 (5) | 0.0155 (5) | 0.0034 (5) |
C31 | 0.0317 (5) | 0.0293 (5) | 0.0306 (5) | −0.0022 (4) | 0.0124 (4) | −0.0004 (4) |
C32 | 0.0384 (6) | 0.0280 (6) | 0.0317 (5) | −0.0011 (5) | 0.0145 (5) | −0.0002 (4) |
C33 | 0.0375 (6) | 0.0374 (6) | 0.0354 (6) | 0.0061 (5) | 0.0147 (5) | 0.0016 (5) |
C34 | 0.0284 (6) | 0.0458 (7) | 0.0442 (7) | 0.0004 (5) | 0.0137 (5) | 0.0007 (5) |
C35 | 0.0341 (6) | 0.0367 (7) | 0.0555 (8) | −0.0072 (5) | 0.0159 (6) | −0.0049 (6) |
C36 | 0.0342 (6) | 0.0295 (6) | 0.0511 (7) | −0.0033 (5) | 0.0172 (5) | −0.0050 (5) |
C6A | 0.0436 (12) | 0.0495 (12) | 0.0643 (13) | −0.0020 (9) | 0.0296 (9) | −0.0051 (9) |
C7A | 0.072 (2) | 0.0563 (16) | 0.0620 (14) | −0.0192 (13) | 0.0121 (12) | 0.0037 (11) |
C6B | 0.044 (4) | 0.060 (5) | 0.049 (4) | −0.006 (3) | 0.008 (3) | 0.001 (3) |
C7B | 0.052 (5) | 0.074 (7) | 0.150 (10) | 0.005 (4) | 0.041 (6) | 0.025 (6) |
O1—C1 | 1.2572 (14) | C15—C16 | 1.3913 (19) |
O2—N5 | 1.2270 (15) | C15—H15 | 0.95 |
O3—N5 | 1.2269 (15) | C16—H16 | 0.95 |
O4—N6 | 1.2268 (18) | C21—C26 | 1.3886 (17) |
O5—N6 | 1.2238 (19) | C21—C22 | 1.3991 (16) |
O6—C6A | 1.432 (2) | C22—C23 | 1.3831 (19) |
O6—C6B | 1.533 (8) | C22—H22 | 0.95 |
O6—H6 | 0.89 (2) | C23—C24 | 1.383 (2) |
N1—N2 | 1.3725 (13) | C23—H23 | 0.95 |
N1—C1 | 1.3767 (14) | C24—C25 | 1.379 (2) |
N1—C11 | 1.4218 (14) | C24—H24 | 0.95 |
N2—C3 | 1.3358 (15) | C25—C26 | 1.3895 (18) |
N2—H2N | 0.936 (18) | C25—H25 | 0.95 |
N3—C5 | 1.2942 (15) | C26—H26 | 0.95 |
N3—N4 | 1.3801 (14) | C31—C36 | 1.4206 (16) |
N4—C31 | 1.3554 (15) | C31—C32 | 1.4219 (16) |
N4—H4N | 0.915 (17) | C32—C33 | 1.3864 (17) |
N5—C32 | 1.4512 (15) | C33—C34 | 1.3696 (19) |
N6—C34 | 1.4496 (17) | C33—H33 | 0.95 |
C1—C2 | 1.4251 (15) | C34—C35 | 1.3948 (19) |
C2—C3 | 1.3888 (16) | C35—C36 | 1.3626 (18) |
C2—C5 | 1.4718 (15) | C35—H35 | 0.95 |
C3—C4 | 1.4931 (17) | C36—H36 | 0.95 |
C4—H4A | 0.98 | C6A—C7A | 1.479 (3) |
C4—H4B | 0.98 | C6A—H6AA | 0.99 |
C4—H4C | 0.98 | C6A—H6AB | 0.99 |
C5—C21 | 1.4873 (16) | C7A—H7AA | 0.98 |
C11—C12 | 1.3856 (18) | C7A—H7AB | 0.98 |
C11—C16 | 1.3863 (18) | C7A—H7AC | 0.98 |
C12—C13 | 1.3891 (19) | C6B—C7B | 1.466 (13) |
C12—H12 | 0.95 | C6B—H6BA | 0.99 |
C13—C14 | 1.380 (2) | C6B—H6BB | 0.99 |
C13—H13 | 0.95 | C7B—H7BA | 0.98 |
C14—C15 | 1.377 (2) | C7B—H7BB | 0.98 |
C14—H14 | 0.95 | C7B—H7BC | 0.98 |
C6A—O6—H6 | 111.1 (13) | C26—C21—C22 | 118.61 (11) |
C6B—O6—H6 | 105.4 (13) | C26—C21—C5 | 120.47 (10) |
N2—N1—C1 | 109.04 (9) | C22—C21—C5 | 120.91 (11) |
N2—N1—C11 | 122.07 (9) | C23—C22—C21 | 120.16 (12) |
C1—N1—C11 | 128.75 (10) | C23—C22—H22 | 119.9 |
C3—N2—N1 | 109.19 (9) | C21—C22—H22 | 119.9 |
C3—N2—H2N | 127.5 (11) | C24—C23—C22 | 120.63 (13) |
N1—N2—H2N | 122.9 (11) | C24—C23—H23 | 119.7 |
C5—N3—N4 | 118.09 (10) | C22—C23—H23 | 119.7 |
C31—N4—N3 | 117.20 (10) | C25—C24—C23 | 119.72 (13) |
C31—N4—H4N | 121.1 (10) | C25—C24—H24 | 120.1 |
N3—N4—H4N | 119.6 (10) | C23—C24—H24 | 120.1 |
O3—N5—O2 | 122.46 (11) | C24—C25—C26 | 120.00 (13) |
O3—N5—C32 | 118.84 (11) | C24—C25—H25 | 120.0 |
O2—N5—C32 | 118.70 (10) | C26—C25—H25 | 120.0 |
O5—N6—O4 | 123.14 (13) | C21—C26—C25 | 120.84 (12) |
O5—N6—C34 | 117.91 (13) | C21—C26—H26 | 119.6 |
O4—N6—C34 | 118.95 (13) | C25—C26—H26 | 119.6 |
O1—C1—N1 | 123.79 (10) | N4—C31—C36 | 119.51 (11) |
O1—C1—C2 | 130.26 (10) | N4—C31—C32 | 124.10 (10) |
N1—C1—C2 | 105.94 (9) | C36—C31—C32 | 116.37 (10) |
C3—C2—C1 | 106.92 (10) | C33—C32—C31 | 121.72 (11) |
C3—C2—C5 | 128.31 (10) | C33—C32—N5 | 115.87 (11) |
C1—C2—C5 | 124.77 (10) | C31—C32—N5 | 122.41 (11) |
N2—C3—C2 | 108.91 (10) | C34—C33—C32 | 119.12 (11) |
N2—C3—C4 | 119.43 (11) | C34—C33—H33 | 120.4 |
C2—C3—C4 | 131.56 (11) | C32—C33—H33 | 120.4 |
C3—C4—H4A | 109.5 | C33—C34—C35 | 121.37 (11) |
C3—C4—H4B | 109.5 | C33—C34—N6 | 119.33 (12) |
H4A—C4—H4B | 109.5 | C35—C34—N6 | 119.30 (12) |
C3—C4—H4C | 109.5 | C36—C35—C34 | 119.71 (12) |
H4A—C4—H4C | 109.5 | C36—C35—H35 | 120.1 |
H4B—C4—H4C | 109.5 | C34—C35—H35 | 120.1 |
N3—C5—C2 | 125.94 (10) | C35—C36—C31 | 121.70 (12) |
N3—C5—C21 | 115.07 (10) | C35—C36—H36 | 119.1 |
C2—C5—C21 | 119.00 (10) | C31—C36—H36 | 119.1 |
C12—C11—C16 | 121.32 (12) | O6—C6A—C7A | 111.5 (2) |
C12—C11—N1 | 118.94 (11) | O6—C6A—H6AA | 109.3 |
C16—C11—N1 | 119.74 (11) | C7A—C6A—H6AA | 109.3 |
C11—C12—C13 | 118.93 (13) | O6—C6A—H6AB | 109.3 |
C11—C12—H12 | 120.5 | C7A—C6A—H6AB | 109.3 |
C13—C12—H12 | 120.5 | H6AA—C6A—H6AB | 108.0 |
C14—C13—C12 | 120.18 (14) | C7B—C6B—O6 | 102.9 (6) |
C14—C13—H13 | 119.9 | C7B—C6B—H6BA | 111.2 |
C12—C13—H13 | 119.9 | O6—C6B—H6BA | 111.2 |
C15—C14—C13 | 120.48 (13) | C7B—C6B—H6BB | 111.2 |
C15—C14—H14 | 119.8 | O6—C6B—H6BB | 111.2 |
C13—C14—H14 | 119.8 | H6BA—C6B—H6BB | 109.1 |
C14—C15—C16 | 120.25 (14) | C6B—C7B—H7BA | 109.5 |
C14—C15—H15 | 119.9 | C6B—C7B—H7BB | 109.5 |
C16—C15—H15 | 119.9 | H7BA—C7B—H7BB | 109.5 |
C11—C16—C15 | 118.82 (13) | C6B—C7B—H7BC | 109.5 |
C11—C16—H16 | 120.6 | H7BA—C7B—H7BC | 109.5 |
C15—C16—H16 | 120.6 | H7BB—C7B—H7BC | 109.5 |
C1—N1—N2—C3 | −0.45 (14) | N3—C5—C21—C26 | −159.14 (11) |
C11—N1—N2—C3 | −176.44 (11) | C2—C5—C21—C26 | 20.72 (16) |
C5—N3—N4—C31 | 163.07 (11) | N3—C5—C21—C22 | 19.34 (16) |
N2—N1—C1—O1 | −179.97 (11) | C2—C5—C21—C22 | −160.80 (11) |
C11—N1—C1—O1 | −4.3 (2) | C26—C21—C22—C23 | −1.49 (19) |
N2—N1—C1—C2 | −0.23 (13) | C5—C21—C22—C23 | 180.00 (12) |
C11—N1—C1—C2 | 175.41 (11) | C21—C22—C23—C24 | −0.1 (2) |
O1—C1—C2—C3 | −179.48 (13) | C22—C23—C24—C25 | 1.3 (2) |
N1—C1—C2—C3 | 0.80 (13) | C23—C24—C25—C26 | −1.0 (2) |
O1—C1—C2—C5 | −0.3 (2) | C22—C21—C26—C25 | 1.82 (19) |
N1—C1—C2—C5 | 179.97 (11) | C5—C21—C26—C25 | −179.67 (12) |
N1—N2—C3—C2 | 0.97 (14) | C24—C25—C26—C21 | −0.6 (2) |
N1—N2—C3—C4 | 177.64 (12) | N3—N4—C31—C36 | −3.89 (17) |
C1—C2—C3—N2 | −1.10 (14) | N3—N4—C31—C32 | 178.08 (11) |
C5—C2—C3—N2 | 179.77 (11) | N4—C31—C32—C33 | 178.43 (11) |
C1—C2—C3—C4 | −177.22 (14) | C36—C31—C32—C33 | 0.34 (17) |
C5—C2—C3—C4 | 3.6 (2) | N4—C31—C32—N5 | −1.50 (18) |
N4—N3—C5—C2 | 0.72 (17) | C36—C31—C32—N5 | −179.59 (11) |
N4—N3—C5—C21 | −179.44 (10) | O3—N5—C32—C33 | −5.39 (17) |
C3—C2—C5—N3 | −134.04 (14) | O2—N5—C32—C33 | 174.35 (12) |
C1—C2—C5—N3 | 46.97 (18) | O3—N5—C32—C31 | 174.54 (12) |
C3—C2—C5—C21 | 46.12 (17) | O2—N5—C32—C31 | −5.72 (18) |
C1—C2—C5—C21 | −132.87 (12) | C31—C32—C33—C34 | −0.20 (18) |
N2—N1—C11—C12 | 131.90 (13) | N5—C32—C33—C34 | 179.73 (11) |
C1—N1—C11—C12 | −43.23 (18) | C32—C33—C34—C35 | 0.1 (2) |
N2—N1—C11—C16 | −48.92 (17) | C32—C33—C34—N6 | −179.53 (12) |
C1—N1—C11—C16 | 135.95 (13) | O5—N6—C34—C33 | 173.35 (16) |
C16—C11—C12—C13 | −1.2 (2) | O4—N6—C34—C33 | −5.9 (2) |
N1—C11—C12—C13 | 177.96 (12) | O5—N6—C34—C35 | −6.3 (2) |
C11—C12—C13—C14 | 1.0 (2) | O4—N6—C34—C35 | 174.49 (15) |
C12—C13—C14—C15 | 0.6 (2) | C33—C34—C35—C36 | −0.1 (2) |
C13—C14—C15—C16 | −1.8 (2) | N6—C34—C35—C36 | 179.48 (13) |
C12—C11—C16—C15 | −0.1 (2) | C34—C35—C36—C31 | 0.3 (2) |
N1—C11—C16—C15 | −179.21 (12) | N4—C31—C36—C35 | −178.57 (12) |
C14—C15—C16—C11 | 1.6 (2) | C32—C31—C36—C35 | −0.39 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4N···O1 | 0.915 (17) | 2.023 (17) | 2.8261 (13) | 145.6 (14) |
N4—H4N···O2 | 0.915 (17) | 2.040 (17) | 2.6497 (14) | 122.8 (13) |
N2—H2N···O6i | 0.936 (18) | 1.711 (18) | 2.6464 (14) | 177.4 (16) |
O6—H6···O1 | 0.89 (2) | 1.72 (2) | 2.5863 (14) | 167 (2) |
Symmetry code: (i) x, −y+3/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C23H18N6O5·C2H6O |
Mr | 504.50 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 200 |
a, b, c (Å) | 12.8289 (4), 14.3247 (4), 14.4213 (4) |
β (°) | 111.347 (1) |
V (Å3) | 2468.38 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.61 × 0.43 × 0.39 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Numerical (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.89, 0.96 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 23873, 6124, 5136 |
Rint | 0.014 |
(sin θ/λ)max (Å−1) | 0.668 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.116, 1.04 |
No. of reflections | 6124 |
No. of parameters | 368 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.28, −0.22 |
Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and SHELXLE (Hübschle et al., 2011), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009) and publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4N···O1 | 0.915 (17) | 2.023 (17) | 2.8261 (13) | 145.6 (14) |
N4—H4N···O2 | 0.915 (17) | 2.040 (17) | 2.6497 (14) | 122.8 (13) |
N2—H2N···O6i | 0.936 (18) | 1.711 (18) | 2.6464 (14) | 177.4 (16) |
O6—H6···O1 | 0.89 (2) | 1.72 (2) | 2.5863 (14) | 167.(2) |
Symmetry code: (i) x, −y+3/2, z−1/2. |
Acknowledgements
The authors would like to thank the Department of Chemistry and Govan Mbeki Research and Development Centre (GMRDC) both of the University of Fort Hare for their support.
References
Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hübschle, C. B., Sheldrick, G. M. & Dittrich, B. (2011). J. Appl. Cryst. 44, 1281–1284. Web of Science CrossRef IUCr Journals Google Scholar
Idemudia, O. G., Sadimenko, A. P., Afolayan, A. J. & Hosten, E. C. (2012). Acta Cryst. E68, o1280–o1281. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals 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.
Acylpyrazolone derived heterocycles have received considerable research interest due to their versatile reactivity and enormous applications. So have phenylhydrazine Schiff bases and its derivatives. We have reported the crystal structure of a phenyl hydrazone with 4-benzoyl-3-methyl-1-phenyl-2-pyrazolin-5-one (Idemudia et al., 2012). Presented herein is the crystal structure report of an acylpyrazolone based dinitrophenyl hydrazone in continuation of our probe on acylpyrazolone Schiff bases.
In the titled compound the least square plane of the pyrazolone ring makes a dihedral angle of 53.56 (3) ° with the least square plane of all the phenyl rings C11–C16, C21–C26, and C31–C36. The largest deviation distance from the phenyl ring plane is C14 at 0.2688 (16) Å. The dihedral angles with the individual least square planes through the phenyl rings with the pyrazolone plane are 45.87 (7) °, 58.29 (7) ° and 55.84 (7) ° repectively. The ethyl group of the ethanol solvent molecule is disordered over two set of sites [occupancy ratio 0.762 (5):0.238 (5)].
H4N, the hydrogen on N4, has two intra molecular contacts of 2.023 (17) Å and 2.040 (17) Å with O1 and O2 respectievly (Table 1). A C36—H36···N3 intra molecular contact of 2.34 Å also occurs. Molecules of the title compound are stacked in the c axis direction and linked via the ethanol solvent molecule with N2—H2N···O6 and O6—H6···O1 inter molecular contacts of length 1.711 (18) Å and 1.72 (2) Å respectively (Figure 2). Adjacent molecules have a C26—H26···O5 interaction of 2.43 Å (Table 1).