1-[3,5-Bis(4-chloro-phen-yl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone.

In the title compound, C(17)H(14)Cl(2)N(2)O, the dihedral angles between the pyrazole ring and the mean planes of the benzene and chloro-substituted benzene rings are 75.97 (1) and 16.63 (1)° respectively. In the crystal, two weak C-H⋯O inter-molecular hydrogen bonds and π-π stacking inter-actions [centroid-centroid distances = 3.774 (4) and 3.716 (7) Å] are observed.

Related literature

For the anti­tumor, anti­bacterial, anti­fungal, anti­viral, anti­parasitic, anti-tubercular and insecticidal properties of substituted pyrazolines, see: Hes et al. (1978 ▶); Manna et al. (2005 ▶); Amir et al. (2008 ▶). For their anti-inflammatory, anti-diabetic, anaesthetic and analgesic properties, see: Regaila et al. (1979 ▶). For their use in organic synthesis, see: Klimova et al. (1999 ▶); Bhaskarreddy et al. (1997 ▶). For a continuation of the work on pyrazoline derivatives, see: Samshuddin et al. (2010 ▶); Fun et al. (2010 ▶); Yathirajan et al. (2007a ▶,b ▶); Butcher et al. (2007 ▶). For related structures, see: Jian & Wang (2006 ▶); Anuradha et al. (2008 ▶); Lu et al. (2008 ▶); Jian et al. (2006 ▶); Wang et al. (2005 ▶).

Experimental

Crystal data

C17H14Cl2N2O

M = 333.20

Monoclinic,

a = 6.0716 (9) Å

b = 13.160 (2) Å

c = 19.782 (3) Å

β = 98.412 (2)°

V = 1563.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.42 mm−1

T = 100 K

0.55 × 0.38 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (APEX2; Bruker, 2008 ▶) T min = 0.803, T max = 0.917

18906 measured reflections

4809 independent reflections

4141 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.111

S = 1.44

4809 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810025584/fj2320sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025584/fj2320Isup2.hkl

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

C17H14Cl2N2O	F(000) = 688
Mr = 333.20	Dx = 1.415 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6706 reflections
a = 6.0716 (9) Å	θ = 2.6–30.8°
b = 13.160 (2) Å	µ = 0.42 mm−1
c = 19.782 (3) Å	T = 100 K
β = 98.412 (2)°	Block, colourless
V = 1563.6 (4) Å3	0.55 × 0.38 × 0.21 mm
Z = 4

Bruker APEXII CCD diffractometer	4809 independent reflections
Radiation source: fine-focus sealed tube	4141 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω scans	θmax = 31.3°, θmin = 1.9°
Absorption correction: multi-scan (APEX2; Bruker, 2008)	h = −8→8
Tmin = 0.803, Tmax = 0.917	k = −18→18
18906 measured reflections	l = −28→28

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H-atom parameters constrained
S = 1.44	w = 1/[σ2(Fo2) + (0.0475P)2] where P = (Fo2 + 2Fc2)/3
4809 reflections	(Δ/σ)max = 0.001
200 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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	−0.05600 (5)	0.67498 (2)	0.037299 (16)	0.02593 (9)
Cl2	1.07200 (6)	0.31318 (3)	0.545917 (17)	0.03442 (10)
O1	1.42292 (14)	0.36398 (8)	0.25597 (5)	0.0284 (2)
N1	1.10312 (16)	0.44665 (8)	0.22241 (5)	0.0223 (2)
N2	0.90756 (16)	0.45866 (8)	0.17716 (5)	0.0215 (2)
C1	0.80954 (19)	0.53952 (9)	0.19412 (6)	0.0198 (2)
C2	0.93583 (19)	0.59546 (9)	0.25404 (6)	0.0227 (2)
H2A	0.8438	0.6066	0.2895	0.027*
H2B	0.9900	0.6604	0.2401	0.027*
C3	1.13032 (19)	0.52236 (9)	0.27851 (6)	0.0205 (2)
H3	1.2730	0.5578	0.2802	0.025*
C4	1.11491 (18)	0.47227 (8)	0.34639 (6)	0.0185 (2)
C5	1.29877 (19)	0.46775 (9)	0.39706 (6)	0.0204 (2)
H5	1.4322	0.4973	0.3895	0.024*
C6	1.2861 (2)	0.41974 (9)	0.45879 (6)	0.0226 (2)
H6	1.4100	0.4164	0.4924	0.027*
C7	1.0866 (2)	0.37695 (9)	0.46945 (6)	0.0227 (2)
C8	0.9003 (2)	0.38125 (9)	0.42023 (6)	0.0239 (2)
H8	0.7665	0.3528	0.4285	0.029*
C9	0.91492 (19)	0.42834 (9)	0.35855 (6)	0.0218 (2)
H9	0.7908	0.4308	0.3249	0.026*
C10	0.59722 (19)	0.57204 (8)	0.15606 (6)	0.0189 (2)
C11	0.4946 (2)	0.51628 (9)	0.10008 (6)	0.0230 (2)
H11	0.5614	0.4571	0.0874	0.028*
C12	0.2948 (2)	0.54783 (9)	0.06325 (6)	0.0236 (2)
H12	0.2282	0.5108	0.0257	0.028*
C13	0.19554 (19)	0.63577 (9)	0.08334 (6)	0.0200 (2)
C14	0.2917 (2)	0.69243 (9)	0.13857 (6)	0.0214 (2)
H14	0.2227	0.7510	0.1515	0.026*
C15	0.4939 (2)	0.66028 (9)	0.17462 (6)	0.0214 (2)
H15	0.5610	0.6982	0.2116	0.026*
C16	1.2506 (2)	0.37105 (9)	0.21546 (6)	0.0233 (2)
C17	1.1866 (2)	0.29880 (10)	0.15692 (6)	0.0307 (3)
H17A	1.3052	0.2512	0.1549	0.046*
H17B	1.1597	0.3363	0.1149	0.046*
H17C	1.0539	0.2628	0.1636	0.046*

	U11	U22	U33	U12	U13	U23
Cl1	0.02224 (16)	0.02398 (16)	0.02988 (17)	0.00321 (10)	−0.00184 (11)	−0.00217 (11)
Cl2	0.0471 (2)	0.03506 (19)	0.02341 (17)	−0.00037 (14)	0.01295 (14)	0.00586 (12)
O1	0.0234 (5)	0.0361 (5)	0.0260 (5)	0.0063 (4)	0.0045 (3)	0.0069 (4)
N1	0.0212 (5)	0.0270 (5)	0.0184 (5)	0.0046 (4)	0.0016 (4)	−0.0002 (4)
N2	0.0211 (5)	0.0251 (5)	0.0181 (5)	0.0027 (4)	0.0023 (4)	0.0016 (4)
C1	0.0212 (5)	0.0202 (5)	0.0181 (5)	−0.0008 (4)	0.0034 (4)	0.0016 (4)
C2	0.0245 (6)	0.0202 (6)	0.0229 (6)	0.0004 (4)	0.0010 (4)	0.0009 (4)
C3	0.0194 (5)	0.0212 (5)	0.0203 (5)	−0.0013 (4)	0.0011 (4)	0.0014 (4)
C4	0.0183 (5)	0.0175 (5)	0.0194 (5)	−0.0005 (4)	0.0020 (4)	0.0000 (4)
C5	0.0171 (5)	0.0214 (5)	0.0223 (5)	−0.0033 (4)	0.0015 (4)	−0.0019 (4)
C6	0.0246 (6)	0.0223 (5)	0.0201 (5)	−0.0008 (4)	0.0004 (4)	−0.0023 (4)
C7	0.0301 (6)	0.0200 (5)	0.0194 (5)	0.0003 (4)	0.0087 (5)	−0.0005 (4)
C8	0.0205 (5)	0.0227 (6)	0.0300 (6)	−0.0016 (4)	0.0085 (5)	0.0010 (5)
C9	0.0168 (5)	0.0218 (5)	0.0266 (6)	−0.0009 (4)	0.0021 (4)	−0.0002 (4)
C10	0.0200 (5)	0.0183 (5)	0.0188 (5)	−0.0001 (4)	0.0046 (4)	0.0024 (4)
C11	0.0228 (6)	0.0209 (5)	0.0255 (6)	0.0024 (4)	0.0044 (4)	−0.0043 (4)
C12	0.0227 (6)	0.0218 (6)	0.0259 (6)	0.0000 (4)	0.0018 (4)	−0.0053 (4)
C13	0.0188 (5)	0.0195 (5)	0.0219 (6)	0.0003 (4)	0.0037 (4)	0.0019 (4)
C14	0.0257 (6)	0.0173 (5)	0.0215 (6)	0.0034 (4)	0.0043 (4)	0.0011 (4)
C15	0.0273 (6)	0.0187 (5)	0.0177 (5)	0.0009 (4)	0.0018 (4)	0.0010 (4)
C16	0.0240 (6)	0.0272 (6)	0.0202 (6)	0.0055 (5)	0.0083 (4)	0.0064 (4)
C17	0.0373 (7)	0.0318 (7)	0.0239 (6)	0.0122 (6)	0.0069 (5)	0.0006 (5)

Cl1—C13	1.7382 (12)	C6—H6	0.9300
Cl2—C7	1.7435 (12)	C7—C8	1.3817 (17)
O1—C16	1.2249 (15)	C8—C9	1.3829 (17)
N1—C16	1.3588 (15)	C8—H8	0.9300
N1—N2	1.3875 (14)	C9—H9	0.9300
N1—C3	1.4826 (15)	C10—C15	1.3946 (16)
N2—C1	1.2875 (14)	C10—C11	1.3968 (16)
C1—C10	1.4587 (16)	C11—C12	1.3842 (17)
C1—C2	1.5063 (16)	C11—H11	0.9300
C2—C3	1.5449 (16)	C12—C13	1.3895 (16)
C2—H2A	0.9700	C12—H12	0.9300
C2—H2B	0.9700	C13—C14	1.3799 (17)
C3—C4	1.5110 (16)	C14—C15	1.3923 (17)
C3—H3	0.9800	C14—H14	0.9300
C4—C5	1.3881 (16)	C15—H15	0.9300
C4—C9	1.3972 (16)	C16—C17	1.5049 (18)
C5—C6	1.3871 (16)	C17—H17A	0.9600
C5—H5	0.9300	C17—H17B	0.9600
C6—C7	1.3795 (17)	C17—H17C	0.9600
C16—N1—N2	122.18 (10)	C7—C8—H8	120.4
C16—N1—C3	124.39 (10)	C9—C8—H8	120.4
N2—N1—C3	113.42 (9)	C8—C9—C4	120.47 (11)
C1—N2—N1	108.10 (10)	C8—C9—H9	119.8
N2—C1—C10	121.01 (11)	C4—C9—H9	119.8
N2—C1—C2	114.05 (10)	C15—C10—C11	118.71 (11)
C10—C1—C2	124.93 (10)	C15—C10—C1	120.40 (11)
C1—C2—C3	102.71 (9)	C11—C10—C1	120.88 (10)
C1—C2—H2A	111.2	C12—C11—C10	120.98 (11)
C3—C2—H2A	111.2	C12—C11—H11	119.5
C1—C2—H2B	111.2	C10—C11—H11	119.5
C3—C2—H2B	111.2	C11—C12—C13	118.86 (11)
H2A—C2—H2B	109.1	C11—C12—H12	120.6
N1—C3—C4	110.94 (9)	C13—C12—H12	120.6
N1—C3—C2	100.81 (9)	C14—C13—C12	121.71 (11)
C4—C3—C2	113.97 (9)	C14—C13—Cl1	119.46 (9)
N1—C3—H3	110.3	C12—C13—Cl1	118.82 (9)
C4—C3—H3	110.3	C13—C14—C15	118.71 (11)
C2—C3—H3	110.3	C13—C14—H14	120.6
C5—C4—C9	119.03 (10)	C15—C14—H14	120.6
C5—C4—C3	120.83 (10)	C14—C15—C10	121.01 (11)
C9—C4—C3	120.13 (10)	C14—C15—H15	119.5
C6—C5—C4	120.86 (11)	C10—C15—H15	119.5
C6—C5—H5	119.6	O1—C16—N1	120.13 (12)
C4—C5—H5	119.6	O1—C16—C17	123.72 (11)
C7—C6—C5	118.91 (11)	N1—C16—C17	116.14 (11)
C7—C6—H6	120.5	C16—C17—H17A	109.5
C5—C6—H6	120.5	C16—C17—H17B	109.5
C6—C7—C8	121.49 (11)	H17A—C17—H17B	109.5
C6—C7—Cl2	119.10 (10)	C16—C17—H17C	109.5
C8—C7—Cl2	119.39 (9)	H17A—C17—H17C	109.5
C7—C8—C9	119.23 (11)	H17B—C17—H17C	109.5
C16—N1—N2—C1	−176.08 (10)	Cl2—C7—C8—C9	−177.42 (9)
C3—N1—N2—C1	5.01 (13)	C7—C8—C9—C4	−0.83 (18)
N1—N2—C1—C10	−179.54 (10)	C5—C4—C9—C8	0.14 (17)
N1—N2—C1—C2	1.70 (13)	C3—C4—C9—C8	179.19 (11)
N2—C1—C2—C3	−7.14 (13)	N2—C1—C10—C15	−179.43 (11)
C10—C1—C2—C3	174.16 (10)	C2—C1—C10—C15	−0.81 (17)
C16—N1—C3—C4	−66.76 (14)	N2—C1—C10—C11	−0.06 (17)
N2—N1—C3—C4	112.11 (10)	C2—C1—C10—C11	178.56 (11)
C16—N1—C3—C2	172.18 (11)	C15—C10—C11—C12	0.38 (18)
N2—N1—C3—C2	−8.95 (12)	C1—C10—C11—C12	−179.00 (11)
C1—C2—C3—N1	8.80 (11)	C10—C11—C12—C13	−0.77 (18)
C1—C2—C3—C4	−110.09 (11)	C11—C12—C13—C14	0.43 (18)
N1—C3—C4—C5	113.38 (12)	C11—C12—C13—Cl1	−179.69 (9)
C2—C3—C4—C5	−133.67 (11)	C12—C13—C14—C15	0.28 (18)
N1—C3—C4—C9	−65.65 (13)	Cl1—C13—C14—C15	−179.60 (9)
C2—C3—C4—C9	47.30 (15)	C13—C14—C15—C10	−0.67 (18)
C9—C4—C5—C6	0.53 (17)	C11—C10—C15—C14	0.35 (17)
C3—C4—C5—C6	−178.51 (11)	C1—C10—C15—C14	179.73 (11)
C4—C5—C6—C7	−0.50 (17)	N2—N1—C16—O1	178.94 (10)
C5—C6—C7—C8	−0.21 (18)	C3—N1—C16—O1	−2.28 (18)
C5—C6—C7—Cl2	178.08 (9)	N2—N1—C16—C17	−1.78 (16)
C6—C7—C8—C9	0.87 (18)	C3—N1—C16—C17	177.00 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···Cl1i	0.93	2.80	3.5996 (13)	145
C9—H9···O1ii	0.93	2.59	3.4620 (15)	156

	CgX···CgY (Å)	Cg1···Perp (Å)	Cg2···Perp (Å)	Cg3···Perp (Å)
Cg1···Cg2i	3.774 (4)	-0.283 (8)	-2.559 (6)
Cg1···Cg3ii	3.716 (7)	-3.572 (2)		-3.594 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯Cl1i	0.93	2.80	3.5996 (13)	145
C9—H9⋯O1ii	0.93	2.59	3.4620 (15)	156

Symmetry codes: (i) ; (ii) .