Crystal structure of (E)-4-{[2-(2,4-di­nitro­phen­yl)hydrazin-1-yl­idene]meth­yl}-3-methyl-1-phenyl-5-(1H-pyrrol-1-yl)-1H-pyrazole

Mague, J.T.; Mohamed, S.K.; Akkurt, M.; El-Kashef, H.M.S.; Albayati, M.R.

doi:10.1107/S1600536814024039

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 70| Part 12| December 2014| Pages o1246-o1247

doi:10.1107/S1600536814024039

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Crystal structure of (E)-4-{[2-(2,4-dinitrophenyl)hydrazin-1-ylidene]methyl}-3-methyl-1-phenyl-5-(1H-pyrrol-1-yl)-1H-pyrazole

Joel T. Mague,^a Shaaban K. Mohamed,^b,^c Mehmet Akkurt,^d Hussein M. S. El-Kashef ^e and Mustafa R. Albayati ^f ^*

^aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^eDepartment of Chemistry, Faculty of Science, Assiut University, 71515 Assiut, Egypt, and ^fDepartment of Chemistry, College of Science, Kirkuk University, Kirkuk, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by H. Ishida, Okayama University, Japan (Received 23 October 2014; accepted 31 October 2014; online 8 November 2014)

The title compound, C₂₁H₁₇N₇O₄, is in an `extended' conformation aided by an intramolecular N—H⋯O hydrogen bond. The pyrazole ring makes dihedral angles of 29.17 (6), 65.47 (4) and 9.91 (7)°, respectively, with the phenyl, pyrrole and benzene rings. In the crystal, molecules are connected by pairs of N—H⋯O and C—H⋯O hydrogen bonds, forming inversion dimers which associate into ribbons running along the b axis through complementary C—H⋯O interactions.

Keywords: crystal structure; pyrazole; azopyrazole; hydrogen bonding.

CCDC reference: 1031959

1. Related literature

For the use of pyrazole compounds as building blocks of various heterocyclic compounds, see: Abramov et al. (2001 ); Quiroga et al. (2001 ); Wu et al. (2006 ); El-Emary (2006 ); Rangnekar & Dhamnaskar (1988 ). For the bioactivity of pyrazole-containing compounds, see: Mashevskaya et al. (2001 ); Janus et al. (1999 ); Park et al. (2005 ); Bouabdallah et al. (2006 ); Yıldırım et al. (2005 ); Bailey et al. (1985 ); Chu & Cutler (1986 ). For industrial applications of azopyrazole derivatives, see: Karci & Demircah (2006 ); Vicentini et al. (1998 ).

2. Experimental

2.1. Crystal data

C₂₁H₁₇N₇O₄
M_r = 431.42
Monoclinic, P 2₁ /n
a = 5.7955 (1) Å
b = 15.4472 (4) Å
c = 21.9289 (5) Å
β = 93.831 (1)°
V = 1958.78 (8) Å³
Z = 4
Cu Kα radiation
μ = 0.88 mm⁻¹
T = 150 K
0.17 × 0.10 × 0.09 mm

2.2. Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer
Absorption correction: numerical (SADABS; Bruker, 2014 ) T_min = 0.89, T_max = 0.93
30722 measured reflections
3854 independent reflections
3425 reflections with I > 2σ(I)
R_int = 0.034

2.3. Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.089
S = 1.03
3854 reflections
290 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5A⋯O4	0.92	1.97	2.6208 (13)	126
N5—H5A⋯O4ⁱ	0.92	2.34	3.2065 (13)	158
C15—H15⋯O3ⁱ	0.95	2.59	3.4853 (15)	158
C18—H18⋯O1ⁱⁱ	0.95	2.40	3.1887 (16)	140
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

CCDC reference: 1031959

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814024039/is5380sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814024039/is5380Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814024039/is5380Isup3.cml

checkCIF report

Comment top

Functionalized pyrazoles have received much attention from chemists in recent decades due to their wide use as building blocks of various pyrazole-containing structures such as pyrazoloisoquinolines (Abramov et al., 2001), pyrazolopyrimidines (Quiroga et al., 2001), pyrazolopyridines (Wu et al., 2006), pyrazolopyrazines (El-Emary, 2006) and pyrazolotriazoles (Rangnekar & Dhamnaskar, 1988). In addition, pyrazole-containing compounds have shown outstanding biological activities such as anti-microbial (Mashevskaya et al., 2001), anti-viral (Janus et al., 1999), anti-tumor (Park et al., 2005; Bouabdallah et al., 2006), anti-histaminic (Yıldırım et al., 2005) and anti-depressant (Bailey et al., 1985) applications as well as in insecticides and fungicides (Chu & Cutler, 1986). Some azopyrazole derivatives have many applications in dyes (Karci & Demircah, 2006; Vicentini et al., 1998). In light of these factors, we report here the synthesis and crystal structure determination of the title compound.

The title molecule exists in an "extended" conformation aided by the intramolecular N5—H5A···O4 interaction which is half of the bifurcated hydrogen bonding involving H5a (Fig. 1 and Table 1). The rings C1–C6, N3/C11–C14 and C16–C21, respectively, make dihedral angles of 29.17 (6), 65.47 (4) and 9.91 (7)° with the central N1/N2/C7/C8/C9 ring. In the crystal, complementary N5—H5A···O4ⁱ and C15—H15···O3ⁱ (i: -x, 1 - y, 1 - z) interactions form dimers which are further associated into ribbons running parallel to the b axis through complementary C18—H18···O1ⁱⁱ (ii: -x, 2 - y, 1 - z) interactions (Table 1 and Figs. 2 and 3).

Related literature top

For the use of pyrazole compounds as building blocks of various heterocyclic compounds, see: Abramov et al. (2001); Quiroga et al. (2001); Wu et al. (2006); El-Emary (2006); Rangnekar & Dhamnaskar (1988). For the bioactivity of pyrazole-containing compounds, see: Mashevskaya et al. (2001); Janus et al. (1999); Park et al. (2005); Bouabdallah et al. (2006); Yıldırım et al. (2005); Bailey et al. (1985); Chu & Cutler (1986). For industrial applications of azopyrazole derivatives, see: Karci & Demircah (2006); Vicentini et al. (1998).

Experimental top

In 20 ml of ethanol, a mixture of 5.06 g m (0.02 mol) of 3-methyl-1-phenyl-5-(1H-pyrrol-1-yl)-4,5-dihydro-1H-pyrazole-4-carbaldehyde and 3.96 g m (0.02 mol) of (2,4-dinitrophenyl)hydrazine was heated under reflux for 8 h. The resulting solid product was filtered off, dried under vacuum and crystallized from dioxane to furnish red-orange crystals in a sufficient quality for X-ray diffraction. M.p 491–493 K, yield 71%.

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Numbering scheme for the title molecule. Ellipsoids are drawn at the 50% probability level.

Packing diagram looking down the c axis showing two chains formed by complementary N—H···O and C—H···O interactions and their association through additional C—H···O interactions.

Packing diagram viewed down the a axis showing an edge view of several ribbons.

(E)-4-{[2-(2,4-Dinitrophenyl)hydrazin-1-ylidene]methyl}-3-methyl-1-phenyl-5-(1H-pyrrol-1-yl)-1H-pyrazole top

Crystal data top

C₂₁H₁₇N₇O₄	F(000) = 896
M_r = 431.42	D_x = 1.463 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54178 Å
a = 5.7955 (1) Å	Cell parameters from 9846 reflections
b = 15.4472 (4) Å	θ = 6.3–72.1°
c = 21.9289 (5) Å	µ = 0.88 mm⁻¹
β = 93.831 (1)°	T = 150 K
V = 1958.78 (8) Å³	Column, red-orange
Z = 4	0.17 × 0.10 × 0.09 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3854 independent reflections
Radiation source: INCOATEC IµS micro–focus source	3425 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.034
Detector resolution: 10.4167 pixels mm^-1	θ_max = 72.1°, θ_min = 3.5°
ω scans	h = −7→6
Absorption correction: numerical (SADABS; Bruker, 2014)	k = −19→19
T_min = 0.89, T_max = 0.93	l = −26→26
30722 measured reflections

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)] = 0.033	Hydrogen site location: mixed
wR(F²) = 0.089	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0466P)² + 0.6128P] where P = (F_o² + 2F_c²)/3
3854 reflections	(Δ/σ)_max < 0.001
290 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₁H₁₇N₇O₄	V = 1958.78 (8) Å³
M_r = 431.42	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 5.7955 (1) Å	µ = 0.88 mm⁻¹
b = 15.4472 (4) Å	T = 150 K
c = 21.9289 (5) Å	0.17 × 0.10 × 0.09 mm
β = 93.831 (1)°

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3854 independent reflections
Absorption correction: numerical (SADABS; Bruker, 2014)	3425 reflections with I > 2σ(I)
T_min = 0.89, T_max = 0.93	R_int = 0.034
30722 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.089	H-atom parameters constrained
S = 1.03	Δρ_max = 0.20 e Å⁻³
3854 reflections	Δρ_min = −0.27 e Å⁻³
290 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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.98 Å) while that attached to nitrogen was placed in a location derived from a difference map and its parameters adjusted to give N—H = 0.91 Å. All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms.

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

	x	y	z	U_iso*/U_eq
O1	−0.33378 (17)	0.99482 (6)	0.45404 (5)	0.0375 (2)
O2	−0.58503 (18)	0.90272 (7)	0.41597 (5)	0.0501 (3)
O3	−0.49349 (16)	0.60444 (6)	0.45127 (4)	0.0358 (2)
O4	−0.18232 (15)	0.54965 (6)	0.49537 (4)	0.0332 (2)
N1	0.97263 (17)	0.60556 (6)	0.70725 (5)	0.0242 (2)
N2	0.94167 (18)	0.69340 (6)	0.70316 (5)	0.0269 (2)
N3	0.80335 (16)	0.47264 (6)	0.66558 (4)	0.0232 (2)
N4	0.33730 (17)	0.67100 (7)	0.58210 (5)	0.0256 (2)
N5	0.14465 (17)	0.64891 (6)	0.54543 (5)	0.0258 (2)
H5A	0.1113	0.5925	0.5350	0.031*
N6	−0.40360 (19)	0.92045 (7)	0.44522 (5)	0.0327 (3)
N7	−0.30076 (17)	0.61280 (7)	0.47743 (5)	0.0260 (2)
C1	1.14907 (19)	0.57328 (8)	0.75003 (5)	0.0241 (2)
C2	1.3424 (2)	0.62502 (8)	0.76363 (6)	0.0276 (3)
H2	1.3569	0.6794	0.7440	0.033*
C3	1.5137 (2)	0.59637 (8)	0.80620 (6)	0.0304 (3)
H3	1.6455	0.6315	0.8159	0.036*
C4	1.4935 (2)	0.51679 (9)	0.83452 (6)	0.0312 (3)
H4	1.6119	0.4971	0.8632	0.037*
C5	1.3000 (2)	0.46609 (9)	0.82076 (6)	0.0312 (3)
H5	1.2866	0.4115	0.8402	0.037*
C6	1.1250 (2)	0.49398 (8)	0.77893 (6)	0.0276 (3)
H6	0.9912	0.4594	0.7702	0.033*
C7	0.81077 (19)	0.56305 (8)	0.67051 (5)	0.0226 (2)
C8	0.6671 (2)	0.62469 (7)	0.64242 (5)	0.0230 (2)
C9	0.7576 (2)	0.70498 (8)	0.66482 (5)	0.0249 (2)
C10	0.6691 (2)	0.79431 (8)	0.65187 (6)	0.0316 (3)
H10A	0.7726	0.8365	0.6729	0.047*
H10B	0.5136	0.8000	0.6664	0.047*
H10C	0.6630	0.8050	0.6077	0.047*
C11	0.9756 (2)	0.42083 (8)	0.64524 (6)	0.0304 (3)
H11	1.1119	0.4404	0.6277	0.036*
C12	0.9170 (3)	0.33692 (9)	0.65452 (6)	0.0365 (3)
H12	1.0042	0.2874	0.6445	0.044*
C13	0.7022 (2)	0.33657 (9)	0.68190 (6)	0.0348 (3)
H13	0.6194	0.2868	0.6936	0.042*
C14	0.6360 (2)	0.42042 (8)	0.68838 (6)	0.0284 (3)
H14	0.4988	0.4396	0.7056	0.034*
C15	0.4654 (2)	0.60777 (8)	0.60170 (5)	0.0236 (2)
H15	0.4279	0.5502	0.5895	0.028*
C16	0.0083 (2)	0.71292 (8)	0.52114 (5)	0.0247 (2)
C17	0.0773 (2)	0.80070 (8)	0.52864 (6)	0.0304 (3)
H17	0.2187	0.8136	0.5512	0.037*
C18	−0.0544 (2)	0.86720 (8)	0.50421 (6)	0.0320 (3)
H18	−0.0038	0.9254	0.5096	0.038*
C19	−0.2638 (2)	0.84940 (8)	0.47125 (6)	0.0285 (3)
C20	−0.3414 (2)	0.76630 (8)	0.46297 (5)	0.0269 (3)
H20	−0.4847	0.7551	0.4408	0.032*
C21	−0.2072 (2)	0.69842 (7)	0.48756 (5)	0.0241 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0399 (5)	0.0267 (5)	0.0456 (6)	0.0029 (4)	0.0011 (4)	0.0057 (4)
O2	0.0423 (6)	0.0412 (6)	0.0629 (7)	0.0049 (5)	−0.0245 (5)	0.0074 (5)
O3	0.0296 (5)	0.0349 (5)	0.0410 (5)	−0.0028 (4)	−0.0129 (4)	−0.0048 (4)
O4	0.0302 (5)	0.0241 (5)	0.0442 (5)	0.0018 (4)	−0.0058 (4)	−0.0011 (4)
N1	0.0234 (5)	0.0212 (5)	0.0272 (5)	0.0005 (4)	−0.0034 (4)	−0.0015 (4)
N2	0.0285 (5)	0.0212 (5)	0.0305 (5)	0.0007 (4)	−0.0028 (4)	−0.0014 (4)
N3	0.0242 (5)	0.0210 (5)	0.0240 (5)	0.0003 (4)	−0.0023 (4)	−0.0007 (4)
N4	0.0224 (5)	0.0259 (5)	0.0276 (5)	0.0003 (4)	−0.0039 (4)	−0.0006 (4)
N5	0.0237 (5)	0.0232 (5)	0.0297 (5)	−0.0004 (4)	−0.0052 (4)	−0.0014 (4)
N6	0.0317 (6)	0.0313 (6)	0.0343 (6)	0.0039 (5)	−0.0024 (5)	0.0050 (4)
N7	0.0252 (5)	0.0278 (5)	0.0248 (5)	0.0003 (4)	−0.0012 (4)	−0.0024 (4)
C1	0.0217 (5)	0.0265 (6)	0.0237 (6)	0.0024 (5)	−0.0016 (4)	−0.0029 (5)
C2	0.0267 (6)	0.0250 (6)	0.0306 (6)	−0.0015 (5)	−0.0011 (5)	−0.0014 (5)
C3	0.0241 (6)	0.0318 (7)	0.0343 (7)	−0.0025 (5)	−0.0050 (5)	−0.0052 (5)
C4	0.0273 (6)	0.0343 (7)	0.0308 (6)	0.0015 (5)	−0.0075 (5)	−0.0015 (5)
C5	0.0320 (7)	0.0303 (6)	0.0304 (6)	−0.0020 (5)	−0.0041 (5)	0.0044 (5)
C6	0.0241 (6)	0.0300 (6)	0.0282 (6)	−0.0042 (5)	−0.0024 (5)	0.0011 (5)
C7	0.0219 (5)	0.0229 (6)	0.0228 (6)	−0.0005 (4)	−0.0006 (4)	−0.0016 (4)
C8	0.0232 (6)	0.0229 (6)	0.0229 (6)	0.0006 (4)	0.0008 (4)	−0.0002 (4)
C9	0.0251 (6)	0.0240 (6)	0.0255 (6)	0.0004 (5)	0.0003 (4)	−0.0010 (4)
C10	0.0351 (7)	0.0226 (6)	0.0359 (7)	0.0012 (5)	−0.0053 (5)	−0.0012 (5)
C11	0.0312 (6)	0.0287 (6)	0.0317 (6)	0.0048 (5)	0.0047 (5)	−0.0013 (5)
C12	0.0490 (8)	0.0243 (6)	0.0362 (7)	0.0084 (6)	0.0033 (6)	−0.0006 (5)
C13	0.0465 (8)	0.0247 (6)	0.0329 (7)	−0.0059 (6)	−0.0009 (6)	0.0029 (5)
C14	0.0271 (6)	0.0295 (6)	0.0281 (6)	−0.0031 (5)	−0.0009 (5)	0.0007 (5)
C15	0.0244 (6)	0.0215 (6)	0.0246 (6)	−0.0010 (4)	−0.0001 (4)	−0.0004 (4)
C16	0.0232 (6)	0.0257 (6)	0.0251 (6)	0.0015 (5)	0.0002 (4)	0.0011 (4)
C17	0.0264 (6)	0.0268 (6)	0.0371 (7)	−0.0019 (5)	−0.0059 (5)	0.0011 (5)
C18	0.0306 (7)	0.0250 (6)	0.0396 (7)	−0.0020 (5)	−0.0033 (5)	0.0027 (5)
C19	0.0273 (6)	0.0280 (6)	0.0299 (6)	0.0040 (5)	−0.0014 (5)	0.0045 (5)
C20	0.0243 (6)	0.0310 (6)	0.0251 (6)	0.0019 (5)	−0.0018 (4)	0.0001 (5)
C21	0.0241 (6)	0.0244 (6)	0.0235 (6)	−0.0011 (5)	0.0002 (4)	−0.0012 (4)

Geometric parameters (Å, º) top

O1—N6	1.2291 (15)	C5—H5	0.9500
O2—N6	1.2255 (15)	C6—H6	0.9500
O3—N7	1.2279 (13)	C7—C8	1.3822 (16)
O4—N7	1.2416 (13)	C8—C9	1.4213 (16)
N1—C7	1.3636 (15)	C8—C15	1.4469 (16)
N1—N2	1.3708 (14)	C9—C10	1.4928 (16)
N1—C1	1.4305 (14)	C10—H10A	0.9800
N2—C9	1.3254 (15)	C10—H10B	0.9800
N3—C11	1.3769 (16)	C10—H10C	0.9800
N3—C14	1.3806 (16)	C11—C12	1.3589 (19)
N3—C7	1.4012 (15)	C11—H11	0.9500
N4—C15	1.2834 (16)	C12—C13	1.418 (2)
N4—N5	1.3747 (14)	C12—H12	0.9500
N5—C16	1.3527 (15)	C13—C14	1.3609 (19)
N5—H5A	0.9184	C13—H13	0.9500
N6—C19	1.4579 (16)	C14—H14	0.9500
N7—C21	1.4410 (15)	C15—H15	0.9500
C1—C6	1.3906 (17)	C16—C17	1.4201 (17)
C1—C2	1.3921 (17)	C16—C21	1.4246 (16)
C2—C3	1.3891 (17)	C17—C18	1.3677 (18)
C2—H2	0.9500	C17—H17	0.9500
C3—C4	1.3858 (19)	C18—C19	1.3973 (18)
C3—H3	0.9500	C18—H18	0.9500
C4—C5	1.3847 (18)	C19—C20	1.3683 (18)
C4—H4	0.9500	C20—C21	1.3924 (17)
C5—C6	1.3898 (17)	C20—H20	0.9500

C7—N1—N2	110.87 (9)	N2—C9—C10	119.82 (11)
C7—N1—C1	130.77 (10)	C8—C9—C10	128.81 (11)
N2—N1—C1	118.20 (9)	C9—C10—H10A	109.5
C9—N2—N1	105.75 (9)	C9—C10—H10B	109.5
C11—N3—C14	108.66 (10)	H10A—C10—H10B	109.5
C11—N3—C7	125.81 (10)	C9—C10—H10C	109.5
C14—N3—C7	124.97 (10)	H10A—C10—H10C	109.5
C15—N4—N5	115.85 (10)	H10B—C10—H10C	109.5
C16—N5—N4	118.63 (10)	C12—C11—N3	108.17 (12)
C16—N5—H5A	119.2	C12—C11—H11	125.9
N4—N5—H5A	122.1	N3—C11—H11	125.9
O2—N6—O1	123.59 (11)	C11—C12—C13	107.61 (12)
O2—N6—C19	118.15 (11)	C11—C12—H12	126.2
O1—N6—C19	118.26 (11)	C13—C12—H12	126.2
O3—N7—O4	122.13 (10)	C14—C13—C12	107.58 (12)
O3—N7—C21	119.32 (10)	C14—C13—H13	126.2
O4—N7—C21	118.55 (9)	C12—C13—H13	126.2
C6—C1—C2	120.80 (11)	C13—C14—N3	107.98 (11)
C6—C1—N1	121.12 (11)	C13—C14—H14	126.0
C2—C1—N1	118.04 (11)	N3—C14—H14	126.0
C3—C2—C1	119.34 (12)	N4—C15—C8	119.65 (11)
C3—C2—H2	120.3	N4—C15—H15	120.2
C1—C2—H2	120.3	C8—C15—H15	120.2
C4—C3—C2	120.38 (12)	N5—C16—C17	119.99 (11)
C4—C3—H3	119.8	N5—C16—C21	123.88 (11)
C2—C3—H3	119.8	C17—C16—C21	116.13 (11)
C5—C4—C3	119.70 (12)	C18—C17—C16	121.76 (12)
C5—C4—H4	120.1	C18—C17—H17	119.1
C3—C4—H4	120.1	C16—C17—H17	119.1
C4—C5—C6	120.88 (12)	C17—C18—C19	119.82 (12)
C4—C5—H5	119.6	C17—C18—H18	120.1
C6—C5—H5	119.6	C19—C18—H18	120.1
C5—C6—C1	118.87 (11)	C20—C19—C18	121.32 (11)
C5—C6—H6	120.6	C20—C19—N6	119.01 (11)
C1—C6—H6	120.6	C18—C19—N6	119.67 (11)
N1—C7—C8	107.55 (10)	C19—C20—C21	118.99 (11)
N1—C7—N3	122.82 (10)	C19—C20—H20	120.5
C8—C7—N3	129.63 (10)	C21—C20—H20	120.5
C7—C8—C9	104.47 (10)	C20—C21—C16	121.97 (11)
C7—C8—C15	126.04 (11)	C20—C21—N7	115.90 (10)
C9—C8—C15	129.44 (11)	C16—C21—N7	122.13 (10)
N2—C9—C8	111.35 (10)

C7—N1—N2—C9	1.25 (13)	C14—N3—C11—C12	0.56 (14)
C1—N1—N2—C9	−174.68 (10)	C7—N3—C11—C12	172.24 (11)
C15—N4—N5—C16	−177.12 (11)	N3—C11—C12—C13	−0.41 (15)
C7—N1—C1—C6	−26.82 (18)	C11—C12—C13—C14	0.11 (16)
N2—N1—C1—C6	148.16 (11)	C12—C13—C14—N3	0.22 (15)
C7—N1—C1—C2	155.46 (12)	C11—N3—C14—C13	−0.48 (14)
N2—N1—C1—C2	−29.57 (15)	C7—N3—C14—C13	−172.26 (11)
C6—C1—C2—C3	0.61 (18)	N5—N4—C15—C8	−177.73 (10)
N1—C1—C2—C3	178.34 (11)	C7—C8—C15—N4	175.05 (11)
C1—C2—C3—C4	0.50 (19)	C9—C8—C15—N4	−1.91 (19)
C2—C3—C4—C5	−0.8 (2)	N4—N5—C16—C17	6.28 (17)
C3—C4—C5—C6	−0.1 (2)	N4—N5—C16—C21	−173.53 (11)
C4—C5—C6—C1	1.2 (2)	N5—C16—C17—C18	179.26 (12)
C2—C1—C6—C5	−1.45 (19)	C21—C16—C17—C18	−0.92 (19)
N1—C1—C6—C5	−179.11 (11)	C16—C17—C18—C19	0.5 (2)
N2—N1—C7—C8	−1.12 (13)	C17—C18—C19—C20	0.3 (2)
C1—N1—C7—C8	174.14 (11)	C17—C18—C19—N6	−179.94 (12)
N2—N1—C7—N3	179.54 (10)	O2—N6—C19—C20	−1.03 (18)
C1—N1—C7—N3	−5.19 (19)	O1—N6—C19—C20	178.62 (12)
C11—N3—C7—N1	−60.95 (16)	O2—N6—C19—C18	179.19 (13)
C14—N3—C7—N1	109.43 (13)	O1—N6—C19—C18	−1.16 (18)
C11—N3—C7—C8	119.87 (14)	C18—C19—C20—C21	−0.56 (19)
C14—N3—C7—C8	−69.75 (17)	N6—C19—C20—C21	179.67 (11)
N1—C7—C8—C9	0.52 (12)	C19—C20—C21—C16	0.08 (18)
N3—C7—C8—C9	179.80 (11)	C19—C20—C21—N7	179.52 (11)
N1—C7—C8—C15	−177.05 (11)	N5—C16—C21—C20	−179.55 (11)
N3—C7—C8—C15	2.2 (2)	C17—C16—C21—C20	0.64 (17)
N1—N2—C9—C8	−0.90 (13)	N5—C16—C21—N7	1.04 (18)
N1—N2—C9—C10	177.49 (11)	C17—C16—C21—N7	−178.78 (11)
C7—C8—C9—N2	0.25 (13)	O3—N7—C21—C20	−3.71 (16)
C15—C8—C9—N2	177.71 (11)	O4—N7—C21—C20	176.00 (11)
C7—C8—C9—C10	−177.97 (12)	O3—N7—C21—C16	175.74 (11)
C15—C8—C9—C10	−0.5 (2)	O4—N7—C21—C16	−4.56 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5A···O4	0.92	1.97	2.6208 (13)	126
N5—H5A···O4ⁱ	0.92	2.34	3.2065 (13)	158
C15—H15···O3ⁱ	0.95	2.59	3.4853 (15)	158
C18—H18···O1ⁱⁱ	0.95	2.40	3.1887 (16)	140

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5A···O4	0.92	1.97	2.6208 (13)	126
N5—H5A···O4ⁱ	0.92	2.34	3.2065 (13)	158
C15—H15···O3ⁱ	0.95	2.59	3.4853 (15)	158
C18—H18···O1ⁱⁱ	0.95	2.40	3.1887 (16)	140

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y+2, −z+1.

Acknowledgements

The support of NSF–MRI grant No. 1228232 for the purchase of the diffractometer is gratefully acknowledged. SKM and HSME would also like to thank Prof T. I. El-Emary for his contribution in this study.

References

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Volume 70| Part 12| December 2014| Pages o1246-o1247

doi:10.1107/S1600536814024039

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

Crystal structure of (E)-4-{[2-(2,4-di­nitro­phen­yl)hydrazin-1-yl­­idene]meth­yl}-3-methyl-1-phenyl-5-(1H-pyrrol-1-yl)-1H-pyrazole

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of (E)-4-{[2-(2,4-dinitrophenyl)hydrazin-1-ylidene]methyl}-3-methyl-1-phenyl-5-(1H-pyrrol-1-yl)-1H-pyrazole