Literature DB >> 24940224

N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-di-hydro-1H-pyrazol-4-yl)-2-(4-nitro-phen-yl)acetamide.

Manpreet Kaur1, Jerry P Jasinski2, H S Yathirajan1, B Narayana3, K Byrappa4.   

Abstract

In the title compound, C19H18N4O4, the nitro-phenyl 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 anti-periplanar 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 inter-actions forming R 2 (2)(10) graph-set motifs, link the mol-ecules into chains along [100]. Additional weak C-H⋯O inter-actions involving the nitro-phenyl rings further link the mol-ecules along [001], also forming R 2 (2)(10) graph-set motifs, thereby generating (010) layers.

Entities:  

Year:  2014        PMID： 24940224      PMCID： PMC4051092          DOI： 10.1107/S1600536814009738

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


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 = 366.37 Triclinic, 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[F 2 > 2σ(F 2)] = 0.046 wR(F 2) = 0.129 S = 1.07 3262 reflections 247 parameters H-atom parameters constrained Δρmax = 0.27 e Å−3 Δρmin = −0.21 e Å−3 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. Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814009738/hg5393sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814009738/hg5393Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814009738/hg5393Isup3.cml CCDC reference: 1000268 Additional supporting information: crystallographic information; 3D view; checkCIF report
C19H18N4O4Z = 2
Mr = 366.37F(000) = 384
Triclinic, P1Dx = 1.400 Mg m−3
a = 6.7023 (6) ÅCu Kα radiation, λ = 1.54184 Å
b = 8.6335 (8) ÅCell parameters from 2476 reflections
c = 15.8720 (13) Åθ = 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) Å30.28 × 0.22 × 0.12 mm
Agilent Eos Gemini diffractometer3262 independent reflections
Radiation source: Enhance (Cu) X-ray Source2913 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm-1Rint = 0.030
ω scansθmax = 71.6°, θmin = 5.4°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)h = −4→8
Tmin = 0.851, Tmax = 1.000k = −10→10
5113 measured reflectionsl = −19→19
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.046w = 1/[σ2(Fo2) + (0.0731P)2 + 0.1699P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.129(Δ/σ)max < 0.001
S = 1.07Δρmax = 0.27 e Å−3
3262 reflectionsΔρmin = −0.21 e Å−3
247 parametersExtinction correction: SHELXL2012 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0160 (14)
Primary atom site location: structure-invariant direct methods
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.
xyzUiso*/Ueq
O10.1021 (2)0.22514 (15)0.69436 (8)0.0438 (3)
O20.42534 (16)0.19900 (14)0.42650 (7)0.0318 (3)
O30.5894 (2)0.31428 (19)1.03446 (9)0.0505 (4)
O40.8856 (2)0.18161 (18)1.00103 (10)0.0521 (4)
N10.2446 (2)0.05926 (16)0.60349 (8)0.0288 (3)
H10.3271−0.03000.59830.035*
N2−0.10661 (19)0.30173 (16)0.44159 (8)0.0285 (3)
N30.08379 (19)0.31651 (16)0.39847 (8)0.0273 (3)
N40.6997 (2)0.22341 (17)0.99332 (9)0.0342 (3)
C10.2184 (2)0.10192 (19)0.68181 (10)0.0295 (3)
C20.3372 (3)−0.02284 (19)0.75387 (10)0.0333 (4)
H2A0.2456−0.08930.78780.040*
H2B0.4453−0.09400.72770.040*
C30.4314 (2)0.04908 (18)0.81419 (9)0.0290 (3)
C40.3122 (3)0.1581 (2)0.86039 (11)0.0345 (4)
H40.17270.19240.85160.041*
C50.3993 (3)0.2157 (2)0.91904 (11)0.0347 (4)
H50.31960.28790.95020.042*
C60.6072 (2)0.16397 (18)0.93061 (9)0.0292 (3)
C70.7300 (3)0.0574 (2)0.88551 (11)0.0348 (4)
H70.86980.02470.89400.042*
C80.6403 (3)0.0001 (2)0.82728 (10)0.0336 (4)
H80.7208−0.07210.79640.040*
C90.1396 (2)0.15810 (18)0.53105 (9)0.0273 (3)
C10−0.0656 (2)0.20985 (19)0.52365 (10)0.0288 (3)
C110.2410 (2)0.22118 (18)0.45045 (9)0.0259 (3)
C120.0955 (2)0.35883 (18)0.30627 (10)0.0270 (3)
C13−0.0571 (3)0.33649 (19)0.25914 (10)0.0321 (4)
H13−0.16760.29410.28780.039*
C14−0.0426 (3)0.3779 (2)0.16951 (11)0.0377 (4)
H14−0.14570.36600.13780.045*
C150.1246 (3)0.4370 (2)0.12657 (11)0.0402 (4)
H150.13500.46290.06620.048*
C160.2765 (3)0.4574 (2)0.17385 (11)0.0377 (4)
H160.38960.49550.14490.045*
C170.2615 (2)0.42151 (19)0.26367 (10)0.0319 (4)
H170.36120.43910.29510.038*
C18−0.2656 (2)0.4522 (2)0.42912 (11)0.0346 (4)
H18A−0.24600.51740.46770.052*
H18B−0.39830.42480.44140.052*
H18C−0.25610.51220.37020.052*
C19−0.2353 (3)0.1816 (2)0.58962 (11)0.0402 (4)
H19A−0.26640.26760.62060.060*
H19B−0.19430.07920.62960.060*
H19C−0.35450.17990.56120.060*
U11U22U33U12U13U23
O10.0579 (8)0.0399 (7)0.0327 (6)0.0048 (6)−0.0132 (5)−0.0154 (5)
O20.0265 (6)0.0381 (6)0.0309 (6)−0.0061 (4)−0.0018 (4)−0.0081 (5)
O30.0527 (8)0.0643 (9)0.0441 (8)−0.0095 (7)−0.0063 (6)−0.0315 (7)
O40.0444 (8)0.0567 (8)0.0606 (9)−0.0034 (6)−0.0248 (6)−0.0207 (7)
N10.0320 (7)0.0311 (7)0.0243 (6)−0.0055 (5)−0.0044 (5)−0.0077 (5)
N20.0241 (6)0.0364 (7)0.0266 (7)−0.0075 (5)−0.0009 (5)−0.0088 (5)
N30.0253 (6)0.0338 (7)0.0244 (6)−0.0067 (5)−0.0013 (5)−0.0088 (5)
N40.0423 (8)0.0332 (7)0.0280 (7)−0.0087 (6)−0.0102 (6)−0.0044 (6)
C10.0351 (8)0.0311 (8)0.0252 (7)−0.0097 (6)−0.0051 (6)−0.0075 (6)
C20.0468 (9)0.0282 (8)0.0269 (8)−0.0086 (7)−0.0076 (7)−0.0068 (6)
C30.0401 (9)0.0276 (7)0.0197 (7)−0.0090 (6)−0.0050 (6)−0.0023 (6)
C40.0303 (8)0.0438 (9)0.0318 (8)−0.0058 (7)−0.0037 (6)−0.0135 (7)
C50.0375 (9)0.0380 (9)0.0307 (8)−0.0035 (7)−0.0029 (6)−0.0147 (7)
C60.0371 (8)0.0291 (8)0.0226 (7)−0.0099 (6)−0.0064 (6)−0.0032 (6)
C70.0322 (8)0.0377 (9)0.0328 (8)−0.0025 (6)−0.0080 (6)−0.0065 (7)
C80.0402 (9)0.0307 (8)0.0284 (8)−0.0003 (6)−0.0045 (6)−0.0088 (6)
C90.0318 (8)0.0304 (8)0.0237 (7)−0.0098 (6)−0.0041 (6)−0.0095 (6)
C100.0322 (8)0.0337 (8)0.0252 (7)−0.0118 (6)−0.0017 (6)−0.0107 (6)
C110.0284 (7)0.0275 (7)0.0254 (7)−0.0068 (6)−0.0041 (6)−0.0106 (6)
C120.0324 (8)0.0251 (7)0.0242 (7)−0.0042 (6)−0.0034 (6)−0.0078 (5)
C130.0356 (8)0.0319 (8)0.0310 (8)−0.0077 (6)−0.0064 (6)−0.0085 (6)
C140.0478 (10)0.0357 (9)0.0313 (9)−0.0048 (7)−0.0133 (7)−0.0098 (7)
C150.0567 (11)0.0367 (9)0.0234 (8)−0.0037 (8)−0.0041 (7)−0.0041 (6)
C160.0453 (10)0.0329 (8)0.0311 (9)−0.0073 (7)0.0037 (7)−0.0023 (7)
C170.0345 (8)0.0309 (8)0.0306 (8)−0.0071 (6)−0.0029 (6)−0.0064 (6)
C180.0310 (8)0.0354 (8)0.0390 (9)−0.0041 (6)−0.0019 (6)−0.0137 (7)
C190.0346 (9)0.0571 (11)0.0315 (9)−0.0166 (8)0.0025 (7)−0.0098 (8)
O1—C11.217 (2)C7—H70.9300
O2—C111.2436 (19)C7—C81.384 (2)
O3—N41.2168 (19)C8—H80.9300
O4—N41.2278 (19)C9—C101.357 (2)
N1—H10.8600C9—C111.435 (2)
N1—C11.3630 (19)C10—C191.489 (2)
N1—C91.405 (2)C12—C131.396 (2)
N2—N31.4047 (17)C12—C171.390 (2)
N2—C101.373 (2)C13—H130.9300
N2—C181.473 (2)C13—C141.382 (2)
N3—C111.3905 (19)C14—H140.9300
N3—C121.4206 (19)C14—C151.386 (3)
N4—C61.463 (2)C15—H150.9300
C1—C21.523 (2)C15—C161.386 (3)
C2—H2A0.9700C16—H160.9300
C2—H2B0.9700C16—C171.384 (2)
C2—C31.508 (2)C17—H170.9300
C3—C41.394 (2)C18—H18A0.9600
C3—C81.391 (2)C18—H18B0.9600
C4—H40.9300C18—H18C0.9600
C4—C51.381 (2)C19—H19A0.9600
C5—H50.9300C19—H19B0.9600
C5—C61.382 (2)C19—H19C0.9600
C6—C71.378 (2)
C1—N1—H1119.3N1—C9—C11123.26 (13)
C1—N1—C9121.36 (13)C10—C9—N1127.98 (14)
C9—N1—H1119.3C10—C9—C11108.77 (13)
N3—N2—C18115.56 (12)N2—C10—C19120.59 (14)
C10—N2—N3106.45 (12)C9—C10—N2109.94 (13)
C10—N2—C18120.24 (13)C9—C10—C19129.46 (15)
N2—N3—C12118.84 (12)O2—C11—N3124.28 (14)
C11—N3—N2109.85 (12)O2—C11—C9131.03 (14)
C11—N3—C12125.33 (12)N3—C11—C9104.68 (13)
O3—N4—O4122.92 (14)C13—C12—N3120.30 (14)
O3—N4—C6118.50 (14)C17—C12—N3119.20 (14)
O4—N4—C6118.56 (14)C17—C12—C13120.49 (15)
O1—C1—N1123.02 (14)C12—C13—H13120.3
O1—C1—C2122.67 (14)C14—C13—C12119.43 (16)
N1—C1—C2114.22 (13)C14—C13—H13120.3
C1—C2—H2A108.6C13—C14—H14119.8
C1—C2—H2B108.6C13—C14—C15120.40 (16)
H2A—C2—H2B107.6C15—C14—H14119.8
C3—C2—C1114.64 (13)C14—C15—H15120.1
C3—C2—H2A108.6C14—C15—C16119.79 (15)
C3—C2—H2B108.6C16—C15—H15120.1
C4—C3—C2121.41 (15)C15—C16—H16119.7
C8—C3—C2119.46 (14)C17—C16—C15120.67 (16)
C8—C3—C4119.05 (14)C17—C16—H16119.7
C3—C4—H4119.7C12—C17—H17120.4
C5—C4—C3120.64 (15)C16—C17—C12119.16 (15)
C5—C4—H4119.7C16—C17—H17120.4
C4—C5—H5120.6N2—C18—H18A109.5
C4—C5—C6118.71 (15)N2—C18—H18B109.5
C6—C5—H5120.6N2—C18—H18C109.5
C5—C6—N4118.90 (14)H18A—C18—H18B109.5
C7—C6—N4118.88 (14)H18A—C18—H18C109.5
C7—C6—C5122.21 (14)H18B—C18—H18C109.5
C6—C7—H7120.8C10—C19—H19A109.5
C6—C7—C8118.36 (15)C10—C19—H19B109.5
C8—C7—H7120.8C10—C19—H19C109.5
C3—C8—H8119.5H19A—C19—H19B109.5
C7—C8—C3121.01 (15)H19A—C19—H19C109.5
C7—C8—H8119.5H19B—C19—H19C109.5
O1—C1—C2—C3−43.2 (2)C4—C5—C6—N4−179.40 (14)
O3—N4—C6—C51.4 (2)C4—C5—C6—C70.1 (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—C30.2 (2)
O4—N4—C6—C73.0 (2)C8—C3—C4—C5−0.7 (2)
N1—C1—C2—C3140.27 (14)C9—N1—C1—O11.0 (2)
N1—C9—C10—N2−178.78 (14)C9—N1—C1—C2177.54 (13)
N1—C9—C10—C192.0 (3)C10—N2—N3—C115.88 (16)
N1—C9—C11—O23.9 (2)C10—N2—N3—C12160.12 (13)
N1—C9—C11—N3−177.63 (13)C10—C9—C11—O2−176.07 (15)
N2—N3—C11—O2173.55 (13)C10—C9—C11—N32.41 (16)
N2—N3—C11—C9−5.07 (15)C11—N3—C12—C13130.08 (16)
N2—N3—C12—C13−19.9 (2)C11—N3—C12—C17−49.4 (2)
N2—N3—C12—C17160.63 (13)C11—C9—C10—N21.18 (17)
N3—N2—C10—C9−4.27 (16)C11—C9—C10—C19−178.02 (16)
N3—N2—C10—C19175.01 (13)C12—N3—C11—O221.4 (2)
N3—C12—C13—C14−179.79 (14)C12—N3—C11—C9−157.26 (14)
N3—C12—C17—C16177.76 (14)C12—C13—C14—C151.7 (2)
N4—C6—C7—C8179.08 (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—C11123.16 (16)C14—C15—C16—C17−0.9 (3)
C1—C2—C3—C457.6 (2)C15—C16—C17—C122.4 (2)
C1—C2—C3—C8−125.41 (16)C17—C12—C13—C14−0.3 (2)
C2—C3—C4—C5176.33 (15)C18—N2—N3—C11142.19 (13)
C2—C3—C8—C7−176.71 (15)C18—N2—N3—C12−63.56 (17)
C3—C4—C5—C60.4 (3)C18—N2—C10—C9−138.12 (14)
C4—C3—C8—C70.3 (2)C18—N2—C10—C1941.2 (2)
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.862.032.8658 (18)164
C7—H7···O4ii0.932.543.307 (2)139
C18—H18B···O2iii0.962.563.336 (2)138
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
N1—H1⋯O2i 0.862.032.8658 (18)164
C7—H7⋯O4ii 0.932.543.307 (2)139
C18—H18B⋯O2iii 0.962.563.336 (2)138

Symmetry codes: (i) ; (ii) ; (iii) .

  7 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  2-(2,4-Dichloro-phen-yl)-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide.

Authors:  Ray J Butcher; Aneeka Mahan; P S Nayak; B Narayana; H S Yathirajan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-12-08

3.  Aqua-[N-phenyl-2-(quinolin-8-yl-oxy)acetamide]dinitratozinc(II).

Authors:  Wei-Na Wu; Yuan Wang; Ai-Yun Zhang; Rui-Qi Zhao; Qiu-Fen Wang
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-02-13

4.  N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-di-hydro-1H-pyrazol-4-yl)-2-phenyl-acetamide.

Authors:  Manpreet Kaur; Jerry P Jasinski; Brian J Anderson; H S Yathirajan; B Narayana
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-11-06

5.  N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-[4-(methyl-sulfan-yl)phen-yl]acetamide.

Authors:  Hoong-Kun Fun; Ching Kheng Quah; Prakash S Nayak; B Narayana; B K Sarojini
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-08-11

6.  2-(3,4-Dichloro-phen-yl)-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide.

Authors:  Aneeka Mahan; Ray J Butcher; Prakash S Nayak; B Narayana; H S Yathirajan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-02-20

7.  2-(2,6-Dichloro-phen-yl)-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide.

Authors:  Ray J Butcher; Aneeka Mahan; P S Nayak; B Narayana; H S Yathirajan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-12-08
  7 in total

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