organic compounds
2-(2,4-Dichlorophenyl)-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide
aDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, bLake Braddock Secondary School, 9200 Burke Lake Road, Burke, VA 22015, USA, cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and dDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
*Correspondence e-mail: rbutcher99@yahoo.com
In the 19H17Cl2N3O2, the molecules form dimers of the R22(10) type through N—H⋯O hydrogen bonding. As a result of steric repulsion, the amide group is rotated with respect to both the dichlorophenyl and 2,3-dihydro-1H-pyrazol-4-yl rings, making dihedral angles of 80.70 (13) and 64.82 (12)°, respectively. The dihedral angle between the dichlorophenyl and 2,3-dihydro-1H-pyrazol-4-yl rings is 48.45 (5)° while that between the 2,3-dihydro-1H-pyrazol-4-yl and phenyl rings is 56.33 (6)°.
of the title compound, CRelated literature
For a description of the Cambridge Structural Database, see: Allen (2002). For hydrogen-bond motifs, see: Bernstein et al. (1995). For N-substituted 2-arylacetamides and see: Mijin & Marinkovic (2006); Mijin et al. (2008); Fun et al. (2011a,b); Fun, Shahani et al. (2012); Fun, Quah et al. (2012); Wu et al. (2008, 2010).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis PRO (Agilent, 2011); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
https://doi.org/10.1107/S1600536812049628/bt6879sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812049628/bt6879Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812049628/bt6879Isup3.cml
2,4-Dichlorophenylacetic acid (0.240 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. The contents were poured into 100 ml of ice-cold aqueous hydrochloric acid with stirring, which was extracted thrice with dichloromethane. Organic layer was washed with saturated NaHCO3 solution and brine solution, dried and concentrated under reduced pressure to give the title compound (I). Single crystals were grown from methylene chloride by the slow evaporation method (m.p.: 473–475 K).
The H atoms were placed in calculated positions and refined in the riding mode: N—H = 0.88 Å, C—H = 0.95–0.99 Å with Uiso(H) = 1.5Ueq(C) for methyl H atoms and = 1.2Ueq(O,C) for other H atoms.
N-Substituted 2-arylacetamides are very interesting compounds because of their structural similarity to the lateral chain of natural benzylpenicillin (Mijin et al., 2006, 2008).
are also used as ligands due to their excellent coordination abilities (Wu et al., 2008, 2010). Crystal structures of some acetamide derivatives viz., (2E)-1-(2,5-dimethoxyphenyl)-3-(3-nitrophenyl)prop-2-en-1-one, N-(4-bromophenyl)-2-(naphthalen-1-yl)acetamide, N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-\[4-(methylsulfanyl)phenyl]acetamide, N-(4-bromophenyl)-2-(4-chlorophenyl)acetamide (Fun et al., 2011a; Fun et al., 2011b; Fun, Shahani et al., 2012; Fun, Quah et al., 2012) have been reported. In view of the importance of we report herein the of the title compound (I).In the title compound, I, C19H17Cl2N3O2 the amide group is planar and through N—H···O hydrogen bonding to an adjoining molecule forms dimers of the R22(10) type (Bernstein et al., 1995). Due to steric repulsion the amide group is rotated with respect to both the dichlorophenyl and 2,3-dihydro-1H-pyrazol-4-yl rings with dihedral angles of 80.70 (13)° and 64.82 (12)° respectively. The dihedral angles between the three rings are 48.45 (5)° for the dichlorophenyl and 2,3-dihydro-1H-pyrazol-4-yl rings and and 56.33 (6)° for the 2,3-dihydro-1H-pyrazol-4-yl and phenyl rings, respectively. All other metrical parameters are in the normal ranges (Allen, 2002).
For a description of the Cambridge Structural Database, see: Allen (2002). For hydrogen-bond motifs, see: Bernstein et al. (1995). For N-substituted 2-arylacetamides and
see: Mijin & Marinkovic (2006); Mijin et al. (2008); Fun et al. (2011a,b); Fun, Shahani et al. (2012); Fun, Quah et al. (2012); Wu et al. (2008, 2010).Data collection: CrysAlis PRO (Agilent, 2011); cell
CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C19H17Cl2N3O2 | F(000) = 1616 |
Mr = 390.26 | Dx = 1.374 Mg m−3 |
Monoclinic, C2/c | Cu Kα radiation, λ = 1.54184 Å |
a = 25.1853 (5) Å | Cell parameters from 9236 reflections |
b = 8.18108 (9) Å | θ = 3.5–75.5° |
c = 21.0978 (4) Å | µ = 3.25 mm−1 |
β = 119.772 (3)° | T = 123 K |
V = 3773.26 (16) Å3 | Plate, colorless |
Z = 8 | 0.59 × 0.22 × 0.08 mm |
Agilent Xcalibur (Ruby, Gemini) diffractometer | 3849 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 3663 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
Detector resolution: 10.5081 pixels mm-1 | θmax = 75.7°, θmin = 4.0° |
ω scans | h = −31→31 |
Absorption correction: analytical [CrysAlis PRO (Agilent, 2011), based on expressions derived by Clark & Reid (1995)] | k = −5→10 |
Tmin = 0.429, Tmax = 0.804 | l = −24→26 |
12628 measured reflections |
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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.095 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.053P)2 + 3.0975P] where P = (Fo2 + 2Fc2)/3 |
3849 reflections | (Δ/σ)max = 0.001 |
237 parameters | Δρmax = 0.57 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
C19H17Cl2N3O2 | V = 3773.26 (16) Å3 |
Mr = 390.26 | Z = 8 |
Monoclinic, C2/c | Cu Kα radiation |
a = 25.1853 (5) Å | µ = 3.25 mm−1 |
b = 8.18108 (9) Å | T = 123 K |
c = 21.0978 (4) Å | 0.59 × 0.22 × 0.08 mm |
β = 119.772 (3)° |
Agilent Xcalibur (Ruby, Gemini) diffractometer | 3849 independent reflections |
Absorption correction: analytical [CrysAlis PRO (Agilent, 2011), based on expressions derived by Clark & Reid (1995)] | 3663 reflections with I > 2σ(I) |
Tmin = 0.429, Tmax = 0.804 | Rint = 0.027 |
12628 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.095 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.57 e Å−3 |
3849 reflections | Δρmin = −0.30 e Å−3 |
237 parameters |
Experimental. CrysAlisPro (Agilent Technologies, 2011) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995). |
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 | ||
Cl1 | 0.322039 (15) | 0.55288 (4) | 0.50139 (2) | 0.03074 (11) | |
Cl2 | 0.26743 (2) | 1.17963 (5) | 0.42432 (2) | 0.04088 (13) | |
O1 | 0.48051 (5) | 0.65179 (13) | 0.60154 (6) | 0.0275 (2) | |
O2 | 0.58614 (5) | 0.26875 (13) | 0.77321 (5) | 0.0281 (2) | |
N1 | 0.46909 (5) | 0.42833 (14) | 0.65739 (6) | 0.0225 (2) | |
H1A | 0.4505 | 0.3881 | 0.6799 | 0.027* | |
N2 | 0.54781 (5) | 0.15657 (15) | 0.59681 (6) | 0.0229 (2) | |
N3 | 0.58823 (5) | 0.16033 (15) | 0.67299 (6) | 0.0230 (2) | |
C1 | 0.37725 (6) | 0.80141 (17) | 0.59726 (8) | 0.0237 (3) | |
C2 | 0.33397 (6) | 0.75827 (17) | 0.52636 (8) | 0.0230 (3) | |
C3 | 0.29970 (6) | 0.87188 (18) | 0.47298 (8) | 0.0255 (3) | |
H3A | 0.2701 | 0.8385 | 0.4251 | 0.031* | |
C4 | 0.30983 (7) | 1.03615 (18) | 0.49149 (8) | 0.0263 (3) | |
C5 | 0.35183 (7) | 1.08602 (19) | 0.56138 (9) | 0.0299 (3) | |
H5A | 0.3579 | 1.1989 | 0.5735 | 0.036* | |
C6 | 0.38487 (7) | 0.96809 (19) | 0.61340 (8) | 0.0288 (3) | |
H6A | 0.4136 | 1.0018 | 0.6616 | 0.035* | |
C7 | 0.41457 (7) | 0.67467 (18) | 0.65363 (8) | 0.0276 (3) | |
H7A | 0.3868 | 0.5946 | 0.6574 | 0.033* | |
H7B | 0.4387 | 0.7282 | 0.7018 | 0.033* | |
C8 | 0.45797 (6) | 0.58490 (17) | 0.63435 (7) | 0.0217 (3) | |
C9 | 0.50922 (6) | 0.32646 (16) | 0.64690 (7) | 0.0212 (3) | |
C10 | 0.50219 (6) | 0.26811 (17) | 0.58283 (7) | 0.0220 (3) | |
C11 | 0.45465 (7) | 0.30761 (19) | 0.50647 (8) | 0.0278 (3) | |
H11A | 0.4249 | 0.3838 | 0.5071 | 0.042* | |
H11B | 0.4337 | 0.2070 | 0.4811 | 0.042* | |
H11C | 0.4741 | 0.3580 | 0.4809 | 0.042* | |
C12 | 0.57913 (8) | 0.1578 (2) | 0.55384 (8) | 0.0307 (3) | |
H12A | 0.5490 | 0.1455 | 0.5019 | 0.046* | |
H12B | 0.6084 | 0.0671 | 0.5694 | 0.046* | |
H12C | 0.6010 | 0.2615 | 0.5615 | 0.046* | |
C13 | 0.56376 (6) | 0.25707 (17) | 0.70619 (7) | 0.0219 (3) | |
C14 | 0.62640 (6) | 0.02126 (18) | 0.70612 (7) | 0.0236 (3) | |
C15 | 0.60320 (8) | −0.13441 (19) | 0.68234 (8) | 0.0305 (3) | |
H15A | 0.5620 | −0.1488 | 0.6446 | 0.037* | |
C16 | 0.64078 (10) | −0.2690 (2) | 0.71423 (10) | 0.0428 (4) | |
H16A | 0.6256 | −0.3760 | 0.6978 | 0.051* | |
C17 | 0.70029 (10) | −0.2473 (3) | 0.76984 (10) | 0.0494 (5) | |
H17A | 0.7259 | −0.3395 | 0.7917 | 0.059* | |
C18 | 0.72255 (9) | −0.0917 (3) | 0.79377 (10) | 0.0491 (5) | |
H18A | 0.7634 | −0.0777 | 0.8323 | 0.059* | |
C19 | 0.68580 (7) | 0.0448 (2) | 0.76203 (9) | 0.0352 (4) | |
H19A | 0.7012 | 0.1518 | 0.7784 | 0.042* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.02802 (19) | 0.01940 (18) | 0.0432 (2) | −0.00059 (12) | 0.01644 (16) | −0.00417 (13) |
Cl2 | 0.0505 (2) | 0.0273 (2) | 0.0381 (2) | 0.01167 (16) | 0.01682 (19) | 0.00933 (15) |
O1 | 0.0318 (5) | 0.0260 (5) | 0.0317 (5) | 0.0038 (4) | 0.0210 (4) | 0.0068 (4) |
O2 | 0.0340 (5) | 0.0323 (6) | 0.0187 (5) | 0.0082 (4) | 0.0136 (4) | 0.0003 (4) |
N1 | 0.0281 (6) | 0.0239 (6) | 0.0229 (5) | 0.0047 (5) | 0.0182 (5) | 0.0043 (4) |
N2 | 0.0277 (6) | 0.0261 (6) | 0.0175 (5) | 0.0045 (5) | 0.0131 (5) | 0.0010 (4) |
N3 | 0.0270 (6) | 0.0255 (6) | 0.0182 (5) | 0.0053 (5) | 0.0126 (5) | 0.0010 (4) |
C1 | 0.0260 (6) | 0.0233 (7) | 0.0274 (7) | 0.0042 (5) | 0.0175 (6) | 0.0007 (5) |
C2 | 0.0237 (6) | 0.0177 (6) | 0.0317 (7) | 0.0002 (5) | 0.0169 (6) | −0.0022 (5) |
C3 | 0.0228 (6) | 0.0252 (7) | 0.0283 (7) | 0.0023 (5) | 0.0125 (6) | −0.0013 (6) |
C4 | 0.0279 (7) | 0.0219 (7) | 0.0313 (7) | 0.0060 (5) | 0.0163 (6) | 0.0047 (5) |
C5 | 0.0329 (7) | 0.0199 (7) | 0.0375 (8) | 0.0013 (6) | 0.0178 (6) | −0.0024 (6) |
C6 | 0.0306 (7) | 0.0265 (7) | 0.0279 (7) | 0.0021 (6) | 0.0134 (6) | −0.0042 (6) |
C7 | 0.0343 (7) | 0.0284 (7) | 0.0265 (7) | 0.0083 (6) | 0.0201 (6) | 0.0035 (6) |
C8 | 0.0239 (6) | 0.0239 (7) | 0.0182 (6) | 0.0027 (5) | 0.0112 (5) | 0.0012 (5) |
C9 | 0.0257 (6) | 0.0212 (6) | 0.0210 (6) | 0.0022 (5) | 0.0149 (5) | 0.0028 (5) |
C10 | 0.0259 (6) | 0.0212 (6) | 0.0222 (6) | 0.0017 (5) | 0.0143 (5) | 0.0023 (5) |
C11 | 0.0311 (7) | 0.0315 (8) | 0.0200 (6) | 0.0054 (6) | 0.0122 (6) | 0.0016 (5) |
C12 | 0.0407 (8) | 0.0339 (8) | 0.0276 (7) | 0.0103 (6) | 0.0247 (7) | 0.0049 (6) |
C13 | 0.0265 (6) | 0.0215 (6) | 0.0219 (6) | 0.0011 (5) | 0.0152 (5) | 0.0005 (5) |
C14 | 0.0269 (7) | 0.0276 (7) | 0.0212 (6) | 0.0067 (5) | 0.0157 (6) | 0.0029 (5) |
C15 | 0.0384 (8) | 0.0285 (8) | 0.0274 (7) | 0.0029 (6) | 0.0184 (6) | 0.0018 (6) |
C16 | 0.0682 (12) | 0.0297 (8) | 0.0372 (9) | 0.0139 (8) | 0.0312 (9) | 0.0059 (7) |
C17 | 0.0635 (12) | 0.0501 (11) | 0.0374 (9) | 0.0336 (10) | 0.0273 (9) | 0.0158 (8) |
C18 | 0.0354 (9) | 0.0679 (13) | 0.0355 (9) | 0.0211 (9) | 0.0112 (7) | 0.0108 (9) |
C19 | 0.0299 (7) | 0.0423 (9) | 0.0295 (7) | 0.0038 (7) | 0.0119 (6) | 0.0006 (7) |
Cl1—C2 | 1.7419 (14) | C7—H7A | 0.9900 |
Cl2—C4 | 1.7388 (15) | C7—H7B | 0.9900 |
O1—C8 | 1.2210 (17) | C9—C10 | 1.3597 (19) |
O2—C13 | 1.2390 (17) | C9—C13 | 1.4378 (19) |
N1—C8 | 1.3492 (18) | C10—C11 | 1.4892 (19) |
N1—C9 | 1.4097 (17) | C11—H11A | 0.9800 |
N1—H1A | 0.8800 | C11—H11B | 0.9800 |
N2—C10 | 1.3796 (18) | C11—H11C | 0.9800 |
N2—N3 | 1.4128 (15) | C12—H12A | 0.9800 |
N2—C12 | 1.4678 (17) | C12—H12B | 0.9800 |
N3—C13 | 1.3874 (17) | C12—H12C | 0.9800 |
N3—C14 | 1.4282 (18) | C14—C19 | 1.383 (2) |
C1—C2 | 1.390 (2) | C14—C15 | 1.387 (2) |
C1—C6 | 1.395 (2) | C15—C16 | 1.388 (2) |
C1—C7 | 1.504 (2) | C15—H15A | 0.9500 |
C2—C3 | 1.383 (2) | C16—C17 | 1.381 (3) |
C3—C4 | 1.387 (2) | C16—H16A | 0.9500 |
C3—H3A | 0.9500 | C17—C18 | 1.382 (3) |
C4—C5 | 1.382 (2) | C17—H17A | 0.9500 |
C5—C6 | 1.386 (2) | C18—C19 | 1.392 (3) |
C5—H5A | 0.9500 | C18—H18A | 0.9500 |
C6—H6A | 0.9500 | C19—H19A | 0.9500 |
C7—C8 | 1.5302 (18) | ||
C8—N1—C9 | 122.77 (11) | N1—C9—C13 | 123.13 (12) |
C8—N1—H1A | 118.6 | C9—C10—N2 | 109.64 (12) |
C9—N1—H1A | 118.6 | C9—C10—C11 | 129.58 (13) |
C10—N2—N3 | 106.37 (10) | N2—C10—C11 | 120.77 (12) |
C10—N2—C12 | 120.64 (11) | C10—C11—H11A | 109.5 |
N3—N2—C12 | 113.45 (11) | C10—C11—H11B | 109.5 |
C13—N3—N2 | 109.70 (11) | H11A—C11—H11B | 109.5 |
C13—N3—C14 | 124.55 (11) | C10—C11—H11C | 109.5 |
N2—N3—C14 | 117.97 (11) | H11A—C11—H11C | 109.5 |
C2—C1—C6 | 116.75 (13) | H11B—C11—H11C | 109.5 |
C2—C1—C7 | 121.62 (13) | N2—C12—H12A | 109.5 |
C6—C1—C7 | 121.63 (13) | N2—C12—H12B | 109.5 |
C3—C2—C1 | 123.01 (13) | H12A—C12—H12B | 109.5 |
C3—C2—Cl1 | 117.25 (11) | N2—C12—H12C | 109.5 |
C1—C2—Cl1 | 119.73 (11) | H12A—C12—H12C | 109.5 |
C2—C3—C4 | 117.95 (13) | H12B—C12—H12C | 109.5 |
C2—C3—H3A | 121.0 | O2—C13—N3 | 123.76 (13) |
C4—C3—H3A | 121.0 | O2—C13—C9 | 131.24 (13) |
C5—C4—C3 | 121.51 (14) | N3—C13—C9 | 104.95 (11) |
C5—C4—Cl2 | 120.34 (12) | C19—C14—C15 | 121.28 (14) |
C3—C4—Cl2 | 118.15 (12) | C19—C14—N3 | 119.11 (14) |
C4—C5—C6 | 118.67 (14) | C15—C14—N3 | 119.61 (13) |
C4—C5—H5A | 120.7 | C14—C15—C16 | 119.30 (16) |
C6—C5—H5A | 120.7 | C14—C15—H15A | 120.4 |
C5—C6—C1 | 122.10 (14) | C16—C15—H15A | 120.4 |
C5—C6—H6A | 119.0 | C17—C16—C15 | 120.07 (18) |
C1—C6—H6A | 119.0 | C17—C16—H16A | 120.0 |
C1—C7—C8 | 111.65 (11) | C15—C16—H16A | 120.0 |
C1—C7—H7A | 109.3 | C16—C17—C18 | 120.05 (17) |
C8—C7—H7A | 109.3 | C16—C17—H17A | 120.0 |
C1—C7—H7B | 109.3 | C18—C17—H17A | 120.0 |
C8—C7—H7B | 109.3 | C17—C18—C19 | 120.76 (18) |
H7A—C7—H7B | 108.0 | C17—C18—H18A | 119.6 |
O1—C8—N1 | 123.92 (12) | C19—C18—H18A | 119.6 |
O1—C8—C7 | 122.02 (13) | C14—C19—C18 | 118.54 (17) |
N1—C8—C7 | 114.06 (12) | C14—C19—H19A | 120.7 |
C10—C9—N1 | 127.88 (13) | C18—C19—H19A | 120.7 |
C10—C9—C13 | 108.83 (12) | ||
C10—N2—N3—C13 | 7.36 (15) | N1—C9—C10—C11 | 7.1 (2) |
C12—N2—N3—C13 | 142.30 (12) | C13—C9—C10—C11 | −177.35 (14) |
C10—N2—N3—C14 | 158.08 (12) | N3—N2—C10—C9 | −6.32 (15) |
C12—N2—N3—C14 | −66.98 (16) | C12—N2—C10—C9 | −137.32 (14) |
C6—C1—C2—C3 | 0.5 (2) | N3—N2—C10—C11 | 174.04 (12) |
C7—C1—C2—C3 | −178.87 (13) | C12—N2—C10—C11 | 43.0 (2) |
C6—C1—C2—Cl1 | 179.45 (10) | N2—N3—C13—O2 | 172.17 (13) |
C7—C1—C2—Cl1 | 0.12 (18) | C14—N3—C13—O2 | 23.8 (2) |
C1—C2—C3—C4 | 0.7 (2) | N2—N3—C13—C9 | −5.45 (15) |
Cl1—C2—C3—C4 | −178.31 (10) | C14—N3—C13—C9 | −153.82 (13) |
C2—C3—C4—C5 | −1.4 (2) | C10—C9—C13—O2 | −175.84 (15) |
C2—C3—C4—Cl2 | 179.34 (10) | N1—C9—C13—O2 | 0.0 (2) |
C3—C4—C5—C6 | 0.9 (2) | C10—C9—C13—N3 | 1.53 (15) |
Cl2—C4—C5—C6 | −179.86 (11) | N1—C9—C13—N3 | 177.34 (12) |
C4—C5—C6—C1 | 0.4 (2) | C13—N3—C14—C19 | −72.00 (19) |
C2—C1—C6—C5 | −1.0 (2) | N2—N3—C14—C19 | 142.00 (13) |
C7—C1—C6—C5 | 178.33 (14) | C13—N3—C14—C15 | 107.33 (16) |
C2—C1—C7—C8 | 66.19 (18) | N2—N3—C14—C15 | −38.67 (17) |
C6—C1—C7—C8 | −113.11 (15) | C19—C14—C15—C16 | −1.4 (2) |
C9—N1—C8—O1 | 1.2 (2) | N3—C14—C15—C16 | 179.28 (14) |
C9—N1—C8—C7 | −178.10 (13) | C14—C15—C16—C17 | 1.1 (2) |
C1—C7—C8—O1 | 31.9 (2) | C15—C16—C17—C18 | −0.1 (3) |
C1—C7—C8—N1 | −148.72 (13) | C16—C17—C18—C19 | −0.5 (3) |
C8—N1—C9—C10 | −67.1 (2) | C15—C14—C19—C18 | 0.8 (2) |
C8—N1—C9—C13 | 117.97 (15) | N3—C14—C19—C18 | −179.91 (15) |
N1—C9—C10—N2 | −172.50 (13) | C17—C18—C19—C14 | 0.2 (3) |
C13—C9—C10—N2 | 3.05 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2i | 0.88 | 1.92 | 2.7938 (15) | 171 |
Symmetry code: (i) −x+1, y, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C19H17Cl2N3O2 |
Mr | 390.26 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 123 |
a, b, c (Å) | 25.1853 (5), 8.18108 (9), 21.0978 (4) |
β (°) | 119.772 (3) |
V (Å3) | 3773.26 (16) |
Z | 8 |
Radiation type | Cu Kα |
µ (mm−1) | 3.25 |
Crystal size (mm) | 0.59 × 0.22 × 0.08 |
Data collection | |
Diffractometer | Agilent Xcalibur (Ruby, Gemini) |
Absorption correction | Analytical [CrysAlis PRO (Agilent, 2011), based on expressions derived by Clark & Reid (1995)] |
Tmin, Tmax | 0.429, 0.804 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12628, 3849, 3663 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.629 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.095, 1.05 |
No. of reflections | 3849 |
No. of parameters | 237 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.57, −0.30 |
Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2i | 0.88 | 1.92 | 2.7938 (15) | 171.4 |
Symmetry code: (i) −x+1, y, −z+3/2. |
Acknowledgements
RJB acknowledges the NSF–MRI program (grant No. CHE-0619278) for funds to purchase the diffractometer.
References
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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.
N-Substituted 2-arylacetamides are very interesting 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). Crystal structures of some acetamide derivatives viz., (2E)-1-(2,5-dimethoxyphenyl)-3-(3-nitrophenyl)prop-2-en-1-one, N-(4-bromophenyl)-2-(naphthalen-1-yl)acetamide, N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-\[4-(methylsulfanyl)phenyl]acetamide, N-(4-bromophenyl)-2-(4-chlorophenyl)acetamide (Fun et al., 2011a; Fun et al., 2011b; Fun, Shahani et al., 2012; Fun, Quah et al., 2012) have been reported. In view of the importance of amides we report herein the crystal structure of the title compound (I).
In the title compound, I, C19H17Cl2N3O2 the amide group is planar and through N—H···O hydrogen bonding to an adjoining molecule forms dimers of the R22(10) type (Bernstein et al., 1995). Due to steric repulsion the amide group is rotated with respect to both the dichlorophenyl and 2,3-dihydro-1H-pyrazol-4-yl rings with dihedral angles of 80.70 (13)° and 64.82 (12)° respectively. The dihedral angles between the three rings are 48.45 (5)° for the dichlorophenyl and 2,3-dihydro-1H-pyrazol-4-yl rings and and 56.33 (6)° for the 2,3-dihydro-1H-pyrazol-4-yl and phenyl rings, respectively. All other metrical parameters are in the normal ranges (Allen, 2002).