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

In the title compound, C19H17Cl2N3O2, the amide group is planar and, through N-H⋯O hydrogen bonding to an adjoining mol-ecule, forms dimers of the R2(2)(10) type. As a result of steric repulsion, the amide group is rotated with respect to both the dichloro-phenyl and 2,3-dihydro-1H-pyrazol-4-yl rings, making dihedral angles of 71.63 (11) and 57.93 (10)°, respectively. The dihedral angle between the dichloro-phenyl and 2,3-dihydro-1H-pyrazol-4-yl rings is 76.60 (10)° while that between the 2,3-dihydro-1H-pyrazol-4-yl and phenyl rings is 49.29 (7)°. The crystal structure also features weak C-H⋯O inter-actions.

Related literature

N-Substituted 2-aryl­acetamides are of inter­est because of their structural similarity to the lateral chain of natural benzyl­penicillin, see: Mijin & Marinkovic (2006 ▶); Mijin et al. (2008 ▶). For amides as ligands, see: Wu et al. (2008 ▶, 2010 ▶). For the structures of acetamide derivatives, see: Fun et al. (2011a ▶,b ▶, 2012a ▶,b ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C19H17Cl2N3O2

M = 390.26

Monoclinic,

a = 20.3442 (11) Å

b = 12.1080 (8) Å

c = 14.9500 (8) Å

β = 93.837 (5)°

V = 3674.3 (4) Å3

Z = 8

Cu Kα radiation

μ = 3.34 mm−1

T = 123 K

0.60 × 0.55 × 0.24 mm

Data collection

Agilent Xcalibur (Ruby, Gemini) diffractometer

Absorption correction: analytical [CrysAlis PRO (Agilent, 2011 ▶) based on expressions derived by Clark & Reid (1995 ▶)] T min = 0.276, T max = 0.560

6894 measured reflections

3692 independent reflections

2836 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.185

S = 1.05

3692 reflections

237 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.62 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; 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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681204963X/hg5277sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681204963X/hg5277Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681204963X/hg5277Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H17Cl2N3O2	F(000) = 1616
Mr = 390.26	Dx = 1.411 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -C 2yc	Cell parameters from 2393 reflections
a = 20.3442 (11) Å	θ = 3.0–75.9°
b = 12.1080 (8) Å	µ = 3.34 mm−1
c = 14.9500 (8) Å	T = 123 K
β = 93.837 (5)°	Prism, colorless
V = 3674.3 (4) Å3	0.60 × 0.55 × 0.24 mm
Z = 8

Agilent Xcalibur (Ruby, Gemini) diffractometer	3692 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2836 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
Detector resolution: 10.5081 pixels mm-1	θmax = 76.1°, θmin = 4.3°
ω scans	h = −25→17
Absorption correction: analytical [CrysAlis PRO (Agilent, 2011) based on expressions derived by Clark & Reid (1995)]	k = −14→13
Tmin = 0.276, Tmax = 0.560	l = −18→18
6894 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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.185	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0919P)2 + 2.7039P] where P = (Fo2 + 2Fc2)/3
3692 reflections	(Δ/σ)max < 0.001
237 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.62 e Å−3

Experimental. CrysAlisPro (Agilent Technologies, 2011) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)

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	0.60120 (7)	0.75806 (10)	−0.05511 (9)	0.0942 (4)
Cl2	0.55602 (5)	1.09130 (9)	0.17378 (6)	0.0674 (3)
O1	0.65197 (10)	0.84440 (18)	0.21156 (15)	0.0483 (5)
O2	0.53366 (8)	0.62011 (15)	0.38199 (13)	0.0384 (4)
N1	0.58629 (10)	0.69208 (19)	0.20824 (15)	0.0368 (5)
H1A	0.5532	0.6580	0.1791	0.044*
N2	0.70088 (10)	0.56877 (19)	0.37326 (16)	0.0389 (5)
N3	0.64116 (10)	0.56119 (18)	0.41658 (15)	0.0361 (5)
C1	0.57761 (12)	0.9297 (2)	0.05381 (19)	0.0401 (6)
C2	0.59995 (15)	0.8983 (3)	−0.0287 (2)	0.0517 (7)
C3	0.62067 (15)	0.9765 (4)	−0.0903 (2)	0.0673 (11)
H3A	0.6348	0.9533	−0.1466	0.081*
C4	0.62042 (16)	1.0866 (4)	−0.0685 (3)	0.0630 (10)
H4A	0.6343	1.1397	−0.1100	0.076*
C5	0.60035 (15)	1.1204 (3)	0.0123 (3)	0.0560 (8)
H5A	0.6005	1.1965	0.0276	0.067*
C6	0.57985 (13)	1.0419 (2)	0.0715 (2)	0.0432 (6)
C7	0.55062 (14)	0.8480 (3)	0.1174 (2)	0.0485 (7)
H7A	0.5277	0.7886	0.0820	0.058*
H7B	0.5175	0.8856	0.1522	0.058*
C8	0.60213 (12)	0.7957 (2)	0.18258 (18)	0.0396 (6)
C9	0.62085 (12)	0.6371 (2)	0.27977 (17)	0.0345 (5)
C10	0.68553 (13)	0.6078 (2)	0.28850 (19)	0.0386 (5)
C11	0.73533 (15)	0.6115 (3)	0.2201 (2)	0.0500 (7)
H11A	0.7150	0.6413	0.1639	0.075*
H11B	0.7516	0.5367	0.2098	0.075*
H11C	0.7721	0.6589	0.2415	0.075*
C12	0.74646 (13)	0.4761 (3)	0.3919 (2)	0.0474 (7)
H12A	0.7865	0.4876	0.3600	0.071*
H12B	0.7252	0.4071	0.3716	0.071*
H12C	0.7581	0.4720	0.4565	0.071*
C13	0.59091 (12)	0.60777 (19)	0.36049 (17)	0.0328 (5)
C14	0.64444 (13)	0.5810 (2)	0.51087 (18)	0.0366 (5)
C15	0.69919 (13)	0.6324 (2)	0.55341 (19)	0.0392 (6)
H15A	0.7364	0.6495	0.5209	0.047*
C16	0.69888 (14)	0.6585 (2)	0.6438 (2)	0.0447 (6)
H16A	0.7366	0.6917	0.6736	0.054*
C17	0.64403 (15)	0.6366 (2)	0.6907 (2)	0.0466 (6)
H17A	0.6433	0.6576	0.7519	0.056*
C18	0.58991 (14)	0.5837 (2)	0.6480 (2)	0.0441 (6)
H18A	0.5522	0.5688	0.6802	0.053*
C19	0.59051 (13)	0.5527 (2)	0.55887 (19)	0.0406 (6)
H19A	0.5546	0.5127	0.5308	0.049*

	U11	U22	U33	U12	U13	U23
Cl1	0.0878 (8)	0.0868 (7)	0.1062 (9)	0.0214 (6)	−0.0073 (7)	−0.0455 (7)
Cl2	0.0517 (5)	0.0811 (6)	0.0699 (5)	0.0068 (4)	0.0073 (4)	−0.0209 (4)
O1	0.0335 (10)	0.0511 (11)	0.0600 (12)	−0.0147 (8)	0.0014 (9)	0.0098 (9)
O2	0.0220 (8)	0.0463 (10)	0.0477 (10)	0.0035 (7)	0.0085 (7)	0.0055 (8)
N1	0.0264 (10)	0.0412 (11)	0.0431 (11)	−0.0065 (8)	0.0058 (8)	0.0012 (9)
N2	0.0223 (10)	0.0439 (11)	0.0515 (12)	0.0034 (8)	0.0097 (9)	−0.0044 (9)
N3	0.0215 (9)	0.0405 (11)	0.0472 (12)	0.0016 (8)	0.0083 (8)	0.0018 (9)
C1	0.0233 (11)	0.0518 (15)	0.0453 (14)	−0.0026 (10)	0.0036 (10)	0.0061 (11)
C2	0.0337 (14)	0.071 (2)	0.0501 (16)	0.0045 (13)	0.0039 (12)	−0.0048 (14)
C3	0.0317 (14)	0.130 (4)	0.0406 (15)	0.0040 (18)	0.0074 (11)	0.0080 (19)
C4	0.0306 (14)	0.088 (3)	0.070 (2)	−0.0103 (15)	0.0014 (14)	0.0365 (19)
C5	0.0331 (14)	0.0568 (17)	0.077 (2)	−0.0092 (12)	−0.0039 (14)	0.0207 (15)
C6	0.0254 (11)	0.0506 (15)	0.0537 (15)	−0.0020 (11)	0.0039 (10)	0.0050 (12)
C7	0.0298 (13)	0.0562 (16)	0.0595 (17)	−0.0094 (12)	0.0033 (12)	0.0137 (13)
C8	0.0280 (12)	0.0448 (13)	0.0467 (14)	−0.0078 (10)	0.0085 (10)	0.0042 (11)
C9	0.0266 (11)	0.0348 (11)	0.0430 (12)	−0.0039 (9)	0.0082 (9)	−0.0037 (9)
C10	0.0282 (12)	0.0409 (12)	0.0475 (14)	−0.0041 (10)	0.0100 (10)	−0.0082 (10)
C11	0.0355 (14)	0.0576 (16)	0.0593 (17)	−0.0042 (12)	0.0209 (13)	−0.0130 (13)
C12	0.0279 (12)	0.0502 (15)	0.0635 (17)	0.0105 (11)	−0.0004 (11)	−0.0120 (13)
C13	0.0252 (11)	0.0279 (10)	0.0461 (13)	0.0019 (8)	0.0065 (9)	−0.0012 (9)
C14	0.0294 (12)	0.0336 (11)	0.0473 (14)	0.0026 (9)	0.0060 (10)	0.0025 (10)
C15	0.0302 (12)	0.0343 (12)	0.0537 (15)	0.0016 (9)	0.0073 (11)	0.0012 (10)
C16	0.0391 (14)	0.0386 (13)	0.0559 (16)	−0.0003 (11)	−0.0005 (12)	−0.0042 (11)
C17	0.0465 (16)	0.0466 (14)	0.0469 (14)	0.0079 (12)	0.0047 (12)	−0.0010 (12)
C18	0.0369 (14)	0.0475 (14)	0.0490 (15)	0.0046 (11)	0.0101 (11)	0.0093 (11)
C19	0.0281 (12)	0.0433 (13)	0.0506 (14)	−0.0003 (10)	0.0052 (10)	0.0074 (11)

Cl1—C2	1.744 (4)	C7—H7A	0.9900
Cl2—C6	1.741 (3)	C7—H7B	0.9900
O1—C8	1.227 (3)	C9—C10	1.361 (4)
O2—C13	1.238 (3)	C9—C13	1.433 (3)
N1—C8	1.357 (4)	C10—C11	1.487 (4)
N1—C9	1.407 (3)	C11—H11A	0.9800
N1—H1A	0.8800	C11—H11B	0.9800
N2—C10	1.369 (4)	C11—H11C	0.9800
N2—N3	1.417 (3)	C12—H12A	0.9800
N2—C12	1.470 (3)	C12—H12B	0.9800
N3—C13	1.397 (3)	C12—H12C	0.9800
N3—C14	1.427 (4)	C14—C15	1.392 (4)
C1—C6	1.384 (4)	C14—C19	1.393 (4)
C1—C2	1.395 (4)	C15—C16	1.387 (4)
C1—C7	1.502 (4)	C15—H15A	0.9500
C2—C3	1.405 (5)	C16—C17	1.383 (4)
C3—C4	1.373 (6)	C16—H16A	0.9500
C3—H3A	0.9500	C17—C18	1.391 (4)
C4—C5	1.363 (6)	C17—H17A	0.9500
C4—H4A	0.9500	C18—C19	1.385 (4)
C5—C6	1.381 (4)	C18—H18A	0.9500
C5—H5A	0.9500	C19—H19A	0.9500
C7—C8	1.520 (4)
C8—N1—C9	122.4 (2)	N1—C9—C13	122.6 (2)
C8—N1—H1A	118.8	C9—C10—N2	109.7 (2)
C9—N1—H1A	118.8	C9—C10—C11	128.7 (3)
C10—N2—N3	107.2 (2)	N2—C10—C11	121.5 (3)
C10—N2—C12	122.8 (2)	C10—C11—H11A	109.5
N3—N2—C12	114.4 (2)	C10—C11—H11B	109.5
C13—N3—N2	108.4 (2)	H11A—C11—H11B	109.5
C13—N3—C14	120.6 (2)	C10—C11—H11C	109.5
N2—N3—C14	117.1 (2)	H11A—C11—H11C	109.5
C6—C1—C2	115.4 (3)	H11B—C11—H11C	109.5
C6—C1—C7	122.3 (3)	N2—C12—H12A	109.5
C2—C1—C7	122.3 (3)	N2—C12—H12B	109.5
C1—C2—C3	121.6 (3)	H12A—C12—H12B	109.5
C1—C2—Cl1	118.5 (3)	N2—C12—H12C	109.5
C3—C2—Cl1	119.9 (3)	H12A—C12—H12C	109.5
C4—C3—C2	119.6 (3)	H12B—C12—H12C	109.5
C4—C3—H3A	120.2	O2—C13—N3	123.8 (2)
C2—C3—H3A	120.2	O2—C13—C9	130.5 (2)
C5—C4—C3	120.5 (3)	N3—C13—C9	105.7 (2)
C5—C4—H4A	119.8	C15—C14—C19	120.6 (3)
C3—C4—H4A	119.8	C15—C14—N3	120.6 (2)
C4—C5—C6	118.9 (3)	C19—C14—N3	118.7 (2)
C4—C5—H5A	120.6	C16—C15—C14	119.4 (2)
C6—C5—H5A	120.6	C16—C15—H15A	120.3
C5—C6—C1	124.1 (3)	C14—C15—H15A	120.3
C5—C6—Cl2	116.1 (3)	C17—C16—C15	120.5 (3)
C1—C6—Cl2	119.8 (2)	C17—C16—H16A	119.8
C1—C7—C8	114.5 (2)	C15—C16—H16A	119.8
C1—C7—H7A	108.6	C16—C17—C18	119.7 (3)
C8—C7—H7A	108.6	C16—C17—H17A	120.1
C1—C7—H7B	108.6	C18—C17—H17A	120.1
C8—C7—H7B	108.6	C19—C18—C17	120.6 (3)
H7A—C7—H7B	107.6	C19—C18—H18A	119.7
O1—C8—N1	123.4 (3)	C17—C18—H18A	119.7
O1—C8—C7	123.0 (2)	C18—C19—C14	119.1 (3)
N1—C8—C7	113.5 (2)	C18—C19—H19A	120.4
C10—C9—N1	128.8 (2)	C14—C19—H19A	120.4
C10—C9—C13	108.5 (2)
C10—N2—N3—C13	−6.6 (3)	C13—C9—C10—N2	−4.7 (3)
C12—N2—N3—C13	−146.3 (2)	N1—C9—C10—C11	−9.5 (5)
C10—N2—N3—C14	−147.1 (2)	C13—C9—C10—C11	173.6 (3)
C12—N2—N3—C14	73.2 (3)	N3—N2—C10—C9	7.0 (3)
C6—C1—C2—C3	−2.4 (4)	C12—N2—C10—C9	142.5 (2)
C7—C1—C2—C3	175.4 (3)	N3—N2—C10—C11	−171.5 (2)
C6—C1—C2—Cl1	178.1 (2)	C12—N2—C10—C11	−36.0 (4)
C7—C1—C2—Cl1	−4.1 (4)	N2—N3—C13—O2	−175.1 (2)
C1—C2—C3—C4	1.4 (5)	C14—N3—C13—O2	−36.2 (4)
Cl1—C2—C3—C4	−179.1 (3)	N2—N3—C13—C9	3.7 (3)
C2—C3—C4—C5	0.1 (5)	C14—N3—C13—C9	142.6 (2)
C3—C4—C5—C6	−0.5 (5)	C10—C9—C13—O2	179.2 (3)
C4—C5—C6—C1	−0.7 (5)	N1—C9—C13—O2	2.1 (4)
C4—C5—C6—Cl2	179.2 (2)	C10—C9—C13—N3	0.5 (3)
C2—C1—C6—C5	2.1 (4)	N1—C9—C13—N3	−176.6 (2)
C7—C1—C6—C5	−175.7 (3)	C13—N3—C14—C15	−119.6 (3)
C2—C1—C6—Cl2	−177.8 (2)	N2—N3—C14—C15	15.9 (3)
C7—C1—C6—Cl2	4.5 (4)	C13—N3—C14—C19	57.4 (3)
C6—C1—C7—C8	−93.9 (3)	N2—N3—C14—C19	−167.0 (2)
C2—C1—C7—C8	88.5 (4)	C19—C14—C15—C16	−2.0 (4)
C9—N1—C8—O1	9.2 (4)	N3—C14—C15—C16	175.0 (2)
C9—N1—C8—C7	−168.3 (2)	C14—C15—C16—C17	−1.8 (4)
C1—C7—C8—O1	32.0 (4)	C15—C16—C17—C18	2.8 (4)
C1—C7—C8—N1	−150.6 (3)	C16—C17—C18—C19	0.1 (4)
C8—N1—C9—C10	−61.4 (4)	C17—C18—C19—C14	−3.8 (4)
C8—N1—C9—C13	115.1 (3)	C15—C14—C19—C18	4.8 (4)
N1—C9—C10—N2	172.2 (2)	N3—C14—C19—C18	−172.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.88	1.99	2.845 (3)	164
C7—H7A···O2i	0.99	2.47	3.249 (3)	135
C12—H12A···O1ii	0.98	2.43	3.104 (3)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.88	1.99	2.845 (3)	164
C7—H7A⋯O2i	0.99	2.47	3.249 (3)	135
C12—H12A⋯O1ii	0.98	2.43	3.104 (3)	126

Symmetry codes: (i) ; (ii) .