N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-di­hydro-1H-pyrazol-4-yl)-2-(4-nitro­phen­yl)acetamide

Kaur, M.; Jasinski, J.P.; Yathirajan, H.S.; Narayana, B.; Byrappa, K.

doi:10.1107/S1600536814009738

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 6| June 2014| Pages o636-o637

doi:10.1107/S1600536814009738

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N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-(4-nitrophenyl)acetamide

Manpreet Kaur,^a Jerry P. Jasinski,^b ^* H. S. Yathirajan,^a B. Narayana ^c and K. Byrappa ^d

^aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, ^bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, ^cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^dMaterials Science Center, University of Mysore, Vijyana Bhavan Building, Manasagangothri, Mysore 570 006, India
^*Correspondence e-mail: jjasinski@keene.edu

Edited by P. C. Healy, Griffith University, Australia (Received 26 April 2014; accepted 30 April 2014; online 3 May 2014)

In the title compound, C₁₉H₁₈N₄O₄, the nitrophenyl and phenyl rings are twisted by 67.0 (6) and 37.4 (4)°, respectively, with respect to the pyrazole ring plane [maximum deviation = 0.0042 (16) Å]. The dihedral angle between the mean planes of the phenyl rings is 59.3 (3)°. The amide group, with a C—N—C—C torsion angle of 177.54 (13)°, is twisted away from the plane of the pyrazole ring in an antiperiplanar conformation. In the crystal, N—H⋯O hydrogen bonds involving the carbonyl group on the pyrazole ring and the amide group, together with weak C—H⋯O interactions forming R₂²(10) graph-set motifs, link the molecules into chains along [100]. Additional weak C—H⋯O interactions involving the nitrophenyl rings further link the molecules along [001], also forming R₂²(10) graph-set motifs, thereby generating (010) layers.

CCDC reference: 1000268

Related literature

For the structural similarity of N-substituted 2-arylacetamides to the lateral chain of natural benzylpenicillin, see: Mijin & Marinkovic (2006 ); Mijin et al. (2008 ). For the coordination abilities of amides, see: Wu et al. (2008 , 2010 ). For the pharmaceutical, insecticidal and non-linear properties of pyrazoles, see: Chandrakantha et al. (2013 ); Cheng et al. (2008 ); Hatton et al. (1993 ); Liu et al. (2010 ). For related structures, see: Fun et al. (2012 ); Butcher et al. (2013a ,b ); Kaur et al. (2013 ); Mahan et al. (2013 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₉H₁₈N₄O₄
M_r = 366.37
Triclinic, $[P \overline 1]$
a = 6.7023 (6) Å
b = 8.6335 (8) Å
c = 15.8720 (13) Å
α = 76.305 (7)°
β = 84.399 (7)°
γ = 77.252 (7)°
V = 869.33 (13) Å³
Z = 2
Cu Kα radiation
μ = 0.84 mm⁻¹
T = 173 K
0.28 × 0.22 × 0.12 mm

Data collection

Agilent Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ) T_min = 0.851, T_max = 1.000
5113 measured reflections
3262 independent reflections
2913 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.129
S = 1.07
3262 reflections
247 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.86	2.03	2.8658 (18)	164
C7—H7⋯O4ⁱⁱ	0.93	2.54	3.307 (2)	139
C18—H18B⋯O2ⁱⁱⁱ	0.96	2.56	3.336 (2)	138
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+2, -y, -z+2; (iii) x-1, y, z.

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

CCDC reference: 1000268

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814009738/hg5393sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814009738/hg5393Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814009738/hg5393Isup3.cml

checkCIF report

Comment top

N-Substituted 2-arylacetamides are biologically active compounds because of their structural similarity to the lateral chain of natural benzylpenicillin (Mijin et al., 2006, 2008). Amides are also used as ligands due to their excellent coordination abilities (Wu et al., 2008, 2010). In a variety of biological heterocyclic compounds, N-pyrazole derivatives are of great interest because of their chemical and pharmaceutical properties (Cheng et al., 2008). Some of the N-pyrazole derivatives have been found to exhibit good insecticidal activities (Hatton et al., 1993), antifungal activities (Liu et al., 2010) and non-linear optical properties (Chandrakantha et al., 2013). Crystal structures of some related acetamide and pyrazole derivatives including: N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihrdro-1H-pyrazol-4-yl)-2- [4-(methylsulfanyl)phenyl]acetamide, (Fun et al., 2012), 2-(2,4-dichlorophenyl)-N-(1,5-dimethyl-3-oxo-2- phenyl)-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol- 4-yl)acetamide (Butcher et al., 2013a,b), 2-(3,4-Dichloro phenyl)-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl) acteamide (Mahan et al., 2013) and recently N-(1,5-Dimethyl- 3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-phenylacetamide (Kaur et al., 2013) have been reported. In view of the importance of amide derivatives of pyrazoles, this paper reports the crystal structure of the title compound (I), C₁₉H₁₈N₄O₄.

The title compound, (I), C₁₉H₁₈N₄O₄, crystallizes with one independent molecule in the asymmetric unit (Fig. 1). In the molecule, the pyrazole ring is nearly planar with C9 atom showing a maximum deviation of 0.0042 (16)Å. The mean planes of the 4-nitrophenyl and phenyl rings is twisted with respect to that of the pyrazole ring by 67.0 (6)° and 37.4 (4)°, respectively. The dihedral angle between the mean planes of the two phenyl rings is 59.3 (3)°. The amide group, with a torsion angle of 177.54° is twisted away from the plane of the pyrazole ring in an anti-periplanar conformation. Bond lengths are in normal ranges (Allen et al., 1987). Classical N—H···O intermolecular hydrogen bonds involving the pyrazole ring and the amide group along with weak C—H···O intermolecular interactions forming R₂²(10) graph set motifs link the molecules into chains along [100]. Additional weak C—H···O intermolecular interactions involving the nitrophenyl rings link the molecules further along [001] also forming R₂²(10) graph set motifs and further extending crystal packing into a 2-D supramolecular network (Fig. 2).

Related literature top

For the structural similarity of N-substituted 2-arylacetamides to the lateral chain of natural benzylpenicillin, see: Mijin & Marinkovic (2006); Mijin et al. (2008). For the coordination abilities of amides, see: Wu et al. (2008, 2010). For the pharmaceutical, insecticidal and non-linear properties of pyrazoles, see: Chandrakantha et al. (2013); Cheng et al. (2008); Hatton et al. (1993); Liu et al. (2010). For related structures, see: Fun et al. (2012); Butcher et al. (2013a,b); Kaur et al. (2013); Mahan et al. (2013). For standard bond lengths, see: Allen et al. (1987).

Experimental top

4-Nitrophenylacetic acid (0.181 g, 1 mmol) and 4-aminoantipyrine (0.203 g, 1 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (1.0 g, 0.01 mol) and were dissolved in dichloromethane (20 mL). The mixture was stirred in presence of triethylamine at 273 K for about 3 h (Fig. 3). The reaction completion was confirmed by thin layer chormatography. The contents were poured into 100 ml of ice-cold aqueous hydrochloric acid with stirring, which was extracted thrice with dichloromethane. The organic layer was washed with a saturated NaHCO₃ solution and brine solution, dried and concentrated under reduced pressure to give the title compound, (I). Single crystals were grown from dichloromethane and and further recrystallised from methanol solution by the slow evaporation method which were subsequently used for x-ray studies.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. ORTEP drawing of (I) (C₁₉H₁₈N₄O₄) showing the labeling scheme of the molecule with 30% probability displacement ellipsoids.
	Fig. 2. Molecular packing for (I) viewed along the b axis. Dashed lines indicate N—H···O intermolecular hydrogen bonds and weak C—H···O intermolecular interactions forming R₂²(10) graph set motifs linking the molecules into chains along [100]. Additional weak C—H···O intermolecular interactions involving the nitrophenyl rings link the molecules further along [001] also forming R₂²(10) graph set motifs viewed with dashed lines. H atoms not involved in hydrogen bonding have been removed for clarity.
	Fig. 3. Synthesis scheme of (I).

N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-(4-nitrophenyl)acetamide top

Crystal data top

C₁₉H₁₈N₄O₄	Z = 2
M_r = 366.37	F(000) = 384
Triclinic, P1	D_x = 1.400 Mg m⁻³
a = 6.7023 (6) Å	Cu Kα radiation, λ = 1.54184 Å
b = 8.6335 (8) Å	Cell parameters from 2476 reflections
c = 15.8720 (13) Å	θ = 5.4–71.4°
α = 76.305 (7)°	µ = 0.84 mm⁻¹
β = 84.399 (7)°	T = 173 K
γ = 77.252 (7)°	Block, colourless
V = 869.33 (13) Å³	0.28 × 0.22 × 0.12 mm

Data collection top

Agilent Eos Gemini diffractometer	3262 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2913 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm^-1	R_int = 0.030
ω scans	θ_max = 71.6°, θ_min = 5.4°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	h = −4→8
T_min = 0.851, T_max = 1.000	k = −10→10
5113 measured reflections	l = −19→19

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.046	w = 1/[σ²(F_o²) + (0.0731P)² + 0.1699P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.129	(Δ/σ)_max < 0.001
S = 1.07	Δρ_max = 0.27 e Å⁻³
3262 reflections	Δρ_min = −0.21 e Å⁻³
247 parameters	Extinction correction: SHELXL2012 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0160 (14)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₉H₁₈N₄O₄	γ = 77.252 (7)°
M_r = 366.37	V = 869.33 (13) Å³
Triclinic, P1	Z = 2
a = 6.7023 (6) Å	Cu Kα radiation
b = 8.6335 (8) Å	µ = 0.84 mm⁻¹
c = 15.8720 (13) Å	T = 173 K
α = 76.305 (7)°	0.28 × 0.22 × 0.12 mm
β = 84.399 (7)°

Data collection top

Agilent Eos Gemini diffractometer	3262 independent reflections
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	2913 reflections with I > 2σ(I)
T_min = 0.851, T_max = 1.000	R_int = 0.030
5113 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.07	Δρ_max = 0.27 e Å⁻³
3262 reflections	Δρ_min = −0.21 e Å⁻³
247 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
O1	0.1021 (2)	0.22514 (15)	0.69436 (8)	0.0438 (3)
O2	0.42534 (16)	0.19900 (14)	0.42650 (7)	0.0318 (3)
O3	0.5894 (2)	0.31428 (19)	1.03446 (9)	0.0505 (4)
O4	0.8856 (2)	0.18161 (18)	1.00103 (10)	0.0521 (4)
N1	0.2446 (2)	0.05926 (16)	0.60349 (8)	0.0288 (3)
H1	0.3271	−0.0300	0.5983	0.035*
N2	−0.10661 (19)	0.30173 (16)	0.44159 (8)	0.0285 (3)
N3	0.08379 (19)	0.31651 (16)	0.39847 (8)	0.0273 (3)
N4	0.6997 (2)	0.22341 (17)	0.99332 (9)	0.0342 (3)
C1	0.2184 (2)	0.10192 (19)	0.68181 (10)	0.0295 (3)
C2	0.3372 (3)	−0.02284 (19)	0.75387 (10)	0.0333 (4)
H2A	0.2456	−0.0893	0.7878	0.040*
H2B	0.4453	−0.0940	0.7277	0.040*
C3	0.4314 (2)	0.04908 (18)	0.81419 (9)	0.0290 (3)
C4	0.3122 (3)	0.1581 (2)	0.86039 (11)	0.0345 (4)
H4	0.1727	0.1924	0.8516	0.041*
C5	0.3993 (3)	0.2157 (2)	0.91904 (11)	0.0347 (4)
H5	0.3196	0.2879	0.9502	0.042*
C6	0.6072 (2)	0.16397 (18)	0.93061 (9)	0.0292 (3)
C7	0.7300 (3)	0.0574 (2)	0.88551 (11)	0.0348 (4)
H7	0.8698	0.0247	0.8940	0.042*
C8	0.6403 (3)	0.0001 (2)	0.82728 (10)	0.0336 (4)
H8	0.7208	−0.0721	0.7964	0.040*
C9	0.1396 (2)	0.15810 (18)	0.53105 (9)	0.0273 (3)
C10	−0.0656 (2)	0.20985 (19)	0.52365 (10)	0.0288 (3)
C11	0.2410 (2)	0.22118 (18)	0.45045 (9)	0.0259 (3)
C12	0.0955 (2)	0.35883 (18)	0.30627 (10)	0.0270 (3)
C13	−0.0571 (3)	0.33649 (19)	0.25914 (10)	0.0321 (4)
H13	−0.1676	0.2941	0.2878	0.039*
C14	−0.0426 (3)	0.3779 (2)	0.16951 (11)	0.0377 (4)
H14	−0.1457	0.3660	0.1378	0.045*
C15	0.1246 (3)	0.4370 (2)	0.12657 (11)	0.0402 (4)
H15	0.1350	0.4629	0.0662	0.048*
C16	0.2765 (3)	0.4574 (2)	0.17385 (11)	0.0377 (4)
H16	0.3896	0.4955	0.1449	0.045*
C17	0.2615 (2)	0.42151 (19)	0.26367 (10)	0.0319 (4)
H17	0.3612	0.4391	0.2951	0.038*
C18	−0.2656 (2)	0.4522 (2)	0.42912 (11)	0.0346 (4)
H18A	−0.2460	0.5174	0.4677	0.052*
H18B	−0.3983	0.4248	0.4414	0.052*
H18C	−0.2561	0.5122	0.3702	0.052*
C19	−0.2353 (3)	0.1816 (2)	0.58962 (11)	0.0402 (4)
H19A	−0.2664	0.2676	0.6206	0.060*
H19B	−0.1943	0.0792	0.6296	0.060*
H19C	−0.3545	0.1799	0.5612	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0579 (8)	0.0399 (7)	0.0327 (6)	0.0048 (6)	−0.0132 (5)	−0.0154 (5)
O2	0.0265 (6)	0.0381 (6)	0.0309 (6)	−0.0061 (4)	−0.0018 (4)	−0.0081 (5)
O3	0.0527 (8)	0.0643 (9)	0.0441 (8)	−0.0095 (7)	−0.0063 (6)	−0.0315 (7)
O4	0.0444 (8)	0.0567 (8)	0.0606 (9)	−0.0034 (6)	−0.0248 (6)	−0.0207 (7)
N1	0.0320 (7)	0.0311 (7)	0.0243 (6)	−0.0055 (5)	−0.0044 (5)	−0.0077 (5)
N2	0.0241 (6)	0.0364 (7)	0.0266 (7)	−0.0075 (5)	−0.0009 (5)	−0.0088 (5)
N3	0.0253 (6)	0.0338 (7)	0.0244 (6)	−0.0067 (5)	−0.0013 (5)	−0.0088 (5)
N4	0.0423 (8)	0.0332 (7)	0.0280 (7)	−0.0087 (6)	−0.0102 (6)	−0.0044 (6)
C1	0.0351 (8)	0.0311 (8)	0.0252 (7)	−0.0097 (6)	−0.0051 (6)	−0.0075 (6)
C2	0.0468 (9)	0.0282 (8)	0.0269 (8)	−0.0086 (7)	−0.0076 (7)	−0.0068 (6)
C3	0.0401 (9)	0.0276 (7)	0.0197 (7)	−0.0090 (6)	−0.0050 (6)	−0.0023 (6)
C4	0.0303 (8)	0.0438 (9)	0.0318 (8)	−0.0058 (7)	−0.0037 (6)	−0.0135 (7)
C5	0.0375 (9)	0.0380 (9)	0.0307 (8)	−0.0035 (7)	−0.0029 (6)	−0.0147 (7)
C6	0.0371 (8)	0.0291 (8)	0.0226 (7)	−0.0099 (6)	−0.0064 (6)	−0.0032 (6)
C7	0.0322 (8)	0.0377 (9)	0.0328 (8)	−0.0025 (6)	−0.0080 (6)	−0.0065 (7)
C8	0.0402 (9)	0.0307 (8)	0.0284 (8)	−0.0003 (6)	−0.0045 (6)	−0.0088 (6)
C9	0.0318 (8)	0.0304 (8)	0.0237 (7)	−0.0098 (6)	−0.0041 (6)	−0.0095 (6)
C10	0.0322 (8)	0.0337 (8)	0.0252 (7)	−0.0118 (6)	−0.0017 (6)	−0.0107 (6)
C11	0.0284 (7)	0.0275 (7)	0.0254 (7)	−0.0068 (6)	−0.0041 (6)	−0.0106 (6)
C12	0.0324 (8)	0.0251 (7)	0.0242 (7)	−0.0042 (6)	−0.0034 (6)	−0.0078 (5)
C13	0.0356 (8)	0.0319 (8)	0.0310 (8)	−0.0077 (6)	−0.0064 (6)	−0.0085 (6)
C14	0.0478 (10)	0.0357 (9)	0.0313 (9)	−0.0048 (7)	−0.0133 (7)	−0.0098 (7)
C15	0.0567 (11)	0.0367 (9)	0.0234 (8)	−0.0037 (8)	−0.0041 (7)	−0.0041 (6)
C16	0.0453 (10)	0.0329 (8)	0.0311 (9)	−0.0073 (7)	0.0037 (7)	−0.0023 (7)
C17	0.0345 (8)	0.0309 (8)	0.0306 (8)	−0.0071 (6)	−0.0029 (6)	−0.0064 (6)
C18	0.0310 (8)	0.0354 (8)	0.0390 (9)	−0.0041 (6)	−0.0019 (6)	−0.0137 (7)
C19	0.0346 (9)	0.0571 (11)	0.0315 (9)	−0.0166 (8)	0.0025 (7)	−0.0098 (8)

Geometric parameters (Å, º) top

O1—C1	1.217 (2)	C7—H7	0.9300
O2—C11	1.2436 (19)	C7—C8	1.384 (2)
O3—N4	1.2168 (19)	C8—H8	0.9300
O4—N4	1.2278 (19)	C9—C10	1.357 (2)
N1—H1	0.8600	C9—C11	1.435 (2)
N1—C1	1.3630 (19)	C10—C19	1.489 (2)
N1—C9	1.405 (2)	C12—C13	1.396 (2)
N2—N3	1.4047 (17)	C12—C17	1.390 (2)
N2—C10	1.373 (2)	C13—H13	0.9300
N2—C18	1.473 (2)	C13—C14	1.382 (2)
N3—C11	1.3905 (19)	C14—H14	0.9300
N3—C12	1.4206 (19)	C14—C15	1.386 (3)
N4—C6	1.463 (2)	C15—H15	0.9300
C1—C2	1.523 (2)	C15—C16	1.386 (3)
C2—H2A	0.9700	C16—H16	0.9300
C2—H2B	0.9700	C16—C17	1.384 (2)
C2—C3	1.508 (2)	C17—H17	0.9300
C3—C4	1.394 (2)	C18—H18A	0.9600
C3—C8	1.391 (2)	C18—H18B	0.9600
C4—H4	0.9300	C18—H18C	0.9600
C4—C5	1.381 (2)	C19—H19A	0.9600
C5—H5	0.9300	C19—H19B	0.9600
C5—C6	1.382 (2)	C19—H19C	0.9600
C6—C7	1.378 (2)

C1—N1—H1	119.3	N1—C9—C11	123.26 (13)
C1—N1—C9	121.36 (13)	C10—C9—N1	127.98 (14)
C9—N1—H1	119.3	C10—C9—C11	108.77 (13)
N3—N2—C18	115.56 (12)	N2—C10—C19	120.59 (14)
C10—N2—N3	106.45 (12)	C9—C10—N2	109.94 (13)
C10—N2—C18	120.24 (13)	C9—C10—C19	129.46 (15)
N2—N3—C12	118.84 (12)	O2—C11—N3	124.28 (14)
C11—N3—N2	109.85 (12)	O2—C11—C9	131.03 (14)
C11—N3—C12	125.33 (12)	N3—C11—C9	104.68 (13)
O3—N4—O4	122.92 (14)	C13—C12—N3	120.30 (14)
O3—N4—C6	118.50 (14)	C17—C12—N3	119.20 (14)
O4—N4—C6	118.56 (14)	C17—C12—C13	120.49 (15)
O1—C1—N1	123.02 (14)	C12—C13—H13	120.3
O1—C1—C2	122.67 (14)	C14—C13—C12	119.43 (16)
N1—C1—C2	114.22 (13)	C14—C13—H13	120.3
C1—C2—H2A	108.6	C13—C14—H14	119.8
C1—C2—H2B	108.6	C13—C14—C15	120.40 (16)
H2A—C2—H2B	107.6	C15—C14—H14	119.8
C3—C2—C1	114.64 (13)	C14—C15—H15	120.1
C3—C2—H2A	108.6	C14—C15—C16	119.79 (15)
C3—C2—H2B	108.6	C16—C15—H15	120.1
C4—C3—C2	121.41 (15)	C15—C16—H16	119.7
C8—C3—C2	119.46 (14)	C17—C16—C15	120.67 (16)
C8—C3—C4	119.05 (14)	C17—C16—H16	119.7
C3—C4—H4	119.7	C12—C17—H17	120.4
C5—C4—C3	120.64 (15)	C16—C17—C12	119.16 (15)
C5—C4—H4	119.7	C16—C17—H17	120.4
C4—C5—H5	120.6	N2—C18—H18A	109.5
C4—C5—C6	118.71 (15)	N2—C18—H18B	109.5
C6—C5—H5	120.6	N2—C18—H18C	109.5
C5—C6—N4	118.90 (14)	H18A—C18—H18B	109.5
C7—C6—N4	118.88 (14)	H18A—C18—H18C	109.5
C7—C6—C5	122.21 (14)	H18B—C18—H18C	109.5
C6—C7—H7	120.8	C10—C19—H19A	109.5
C6—C7—C8	118.36 (15)	C10—C19—H19B	109.5
C8—C7—H7	120.8	C10—C19—H19C	109.5
C3—C8—H8	119.5	H19A—C19—H19B	109.5
C7—C8—C3	121.01 (15)	H19A—C19—H19C	109.5
C7—C8—H8	119.5	H19B—C19—H19C	109.5

O1—C1—C2—C3	−43.2 (2)	C4—C5—C6—N4	−179.40 (14)
O3—N4—C6—C5	1.4 (2)	C4—C5—C6—C7	0.1 (3)
O3—N4—C6—C7	−178.19 (15)	C5—C6—C7—C8	−0.5 (2)
O4—N4—C6—C5	−177.43 (15)	C6—C7—C8—C3	0.2 (2)
O4—N4—C6—C7	3.0 (2)	C8—C3—C4—C5	−0.7 (2)
N1—C1—C2—C3	140.27 (14)	C9—N1—C1—O1	1.0 (2)
N1—C9—C10—N2	−178.78 (14)	C9—N1—C1—C2	177.54 (13)
N1—C9—C10—C19	2.0 (3)	C10—N2—N3—C11	5.88 (16)
N1—C9—C11—O2	3.9 (2)	C10—N2—N3—C12	160.12 (13)
N1—C9—C11—N3	−177.63 (13)	C10—C9—C11—O2	−176.07 (15)
N2—N3—C11—O2	173.55 (13)	C10—C9—C11—N3	2.41 (16)
N2—N3—C11—C9	−5.07 (15)	C11—N3—C12—C13	130.08 (16)
N2—N3—C12—C13	−19.9 (2)	C11—N3—C12—C17	−49.4 (2)
N2—N3—C12—C17	160.63 (13)	C11—C9—C10—N2	1.18 (17)
N3—N2—C10—C9	−4.27 (16)	C11—C9—C10—C19	−178.02 (16)
N3—N2—C10—C19	175.01 (13)	C12—N3—C11—O2	21.4 (2)
N3—C12—C13—C14	−179.79 (14)	C12—N3—C11—C9	−157.26 (14)
N3—C12—C17—C16	177.76 (14)	C12—C13—C14—C15	1.7 (2)
N4—C6—C7—C8	179.08 (14)	C13—C12—C17—C16	−1.8 (2)
C1—N1—C9—C10	−56.9 (2)	C13—C14—C15—C16	−1.1 (3)
C1—N1—C9—C11	123.16 (16)	C14—C15—C16—C17	−0.9 (3)
C1—C2—C3—C4	57.6 (2)	C15—C16—C17—C12	2.4 (2)
C1—C2—C3—C8	−125.41 (16)	C17—C12—C13—C14	−0.3 (2)
C2—C3—C4—C5	176.33 (15)	C18—N2—N3—C11	142.19 (13)
C2—C3—C8—C7	−176.71 (15)	C18—N2—N3—C12	−63.56 (17)
C3—C4—C5—C6	0.4 (3)	C18—N2—C10—C9	−138.12 (14)
C4—C3—C8—C7	0.3 (2)	C18—N2—C10—C19	41.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.86	2.03	2.8658 (18)	164
C7—H7···O4ⁱⁱ	0.93	2.54	3.307 (2)	139
C18—H18B···O2ⁱⁱⁱ	0.96	2.56	3.336 (2)	138

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.86	2.03	2.8658 (18)	164.4
C7—H7···O4ⁱⁱ	0.93	2.54	3.307 (2)	139.4
C18—H18B···O2ⁱⁱⁱ	0.96	2.56	3.336 (2)	138.2

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

Acknowledgements

MK is grateful to the CPEPA–UGC for the award of a JRF and thanks the University of Mysore for research facilities. JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

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Volume 70| Part 6| June 2014| Pages o636-o637

doi:10.1107/S1600536814009738

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

N-(1,5-Di­methyl-3-oxo-2-phenyl-2,3-di­hydro-1H-pyrazol-4-yl)-2-(4-nitro­phen­yl)acetamide

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organic compounds

N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-(4-nitrophenyl)acetamide