4-{[2-(2,4-Dinitro­phen­yl)hydrazinyl­idene](phen­yl)meth­yl}-5-methyl-2-phenyl-1H-pyrazol-3(2H)-one ethanol monosolvate

Idemudia, O.G.; Sadimenko, A.P.; Hosten, E.C.

doi:10.1107/S1600536812044935

organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3380

doi:10.1107/S1600536812044935

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4-{[2-(2,4-Dinitrophenyl)hydrazinylidene](phenyl)methyl}-5-methyl-2-phenyl-1H-pyrazol-3(2H)-one ethanol monosolvate

Omoruyi G. Idemudia,^a ^* Alexander P. Sadimenko ^a and Eric C. Hosten ^b

^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

(Received 6 September 2012; accepted 30 October 2012; online 17 November 2012)

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.

Related literature

For a related structure, see: Idemudia et al. (2012 ).

Experimental

Crystal data

C₂₃H₁₈N₆O₅·C₂H₆O
M_r = 504.50
Monoclinic, P 2₁ /c
a = 12.8289 (4) Å
b = 14.3247 (4) Å
c = 14.4213 (4) Å
β = 111.347 (1)°
V = 2468.38 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 200 K
0.61 × 0.43 × 0.39 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: numerical (SADABS; Bruker, 2008 ) T_min = 0.89, T_max = 0.96
23873 measured reflections
6124 independent reflections
5136 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.116
S = 1.04
6124 reflections
368 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2010 ); cell refinement: 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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812044935/ng5294sup1.cif

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

checkCIF report

Comment top

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).

Related literature top

For a related structure, see: Idemudia et al. (2012).

Experimental top

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.

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: 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).

Figures top

	Fig. 1. Molecular structure of the titled compound, with atom labels and displacement ellipsoids drawn at 50% probability level.
	Fig. 2. Selected intra and inter molecular contacts, with displacement ellipsoids drawn at 50% probability level. Symmetry operators: ⁱ x, -y + 3/2, z - 1/2.

4-{[2-(2,4-Dinitrophenyl)hydrazinylidene](phenyl)methyl}-5-methyl-2- phenyl-1H-pyrazol-3(2H)-one ethanol monosolvate top

Crystal data top

C₂₃H₁₈N₆O₅·C₂H₆O	D_x = 1.358 Mg m⁻³
M_r = 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

Data collection top

Bruker APEXII CCD diffractometer	6124 independent reflections
Graphite monochromator	5136 reflections with I > 2σ(I)
Detector resolution: 8.3333 pixels mm^-1	R_int = 0.014
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.2°
Absorption correction: numerical (SADABS; Bruker, 2008)	h = −16→17
T_min = 0.89, T_max = 0.96	k = −13→19
23873 measured reflections	l = −19→19

Refinement top

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(F_o²) + (0.0507P)² + 0.8241P] where P = (F_o² + 2F_c²)/3
6124 reflections	(Δ/σ)_max < 0.001
368 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₃H₁₈N₆O₅·C₂H₆O	V = 2468.38 (12) Å³
M_r = 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)°

Data collection top

Bruker APEXII CCD diffractometer	6124 independent reflections
Absorption correction: numerical (SADABS; Bruker, 2008)	5136 reflections with I > 2σ(I)
T_min = 0.89, T_max = 0.96	R_int = 0.014
23873 measured reflections

Refinement top

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	Δρ_max = 0.28 e Å⁻³
6124 reflections	Δρ_min = −0.22 e Å⁻³
368 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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
M_r	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)
T_min, T_max	0.89, 0.96
No. of measured, independent and observed [I > 2σ(I)] reflections	23873, 6124, 5136
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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

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Volume 68| Part 12| December 2012| Page o3380

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-{[2-(2,4-Di­nitro­phen­yl)hydrazinyl­­idene](phen­yl)meth­yl}-5-methyl-2-phenyl-1H-pyrazol-3(2H)-one ethanol monosolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-{[2-(2,4-Dinitrophenyl)hydrazinylidene](phenyl)methyl}-5-methyl-2-phenyl-1H-pyrazol-3(2H)-one ethanol monosolvate