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

Jasinski, J.P.; Pek, A.E.; Samshuddin, S.; Narayana, B.; Yathirajan, H.S.

doi:10.1107/S1600536810025584

organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Pages o1950-o1951

https://doi.org/10.1107/S1600536810025584

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

Jerry P. Jasinski,^a ^* Albert E. Pek,^a S. Samshuddin,^b B. Narayana ^b and H. S. Yathirajan ^c

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

(Received 14 June 2010; accepted 29 June 2010; online 7 July 2010)

In the title compound, C₁₇H₁₄Cl₂N₂O, 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 intermolecular hydrogen bonds and π–π stacking interactions [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_r = 333.20
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.037
wR(F²) = 0.111
S = 1.44
4809 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.26 e Å⁻³

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) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x-1, y, z.

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810025584/fj2320Isup2.hkl

checkCIF report

Comment top

Due to the interesting activity of variously substituted pyrazolines as biological agents considerable attention has been focused on this class of compounds. They are used as antitumor, antibacterial, antifungal, antiviral, antiparasitic, anti-tubercular and insecticidal agents (Hes et al., 1978; Manna et al. 2005; Amir et al., 2008).Some of these compounds have also anti-inflammatory, anti-diabetic, anaesthetic and analgesic properties Regaila et al., 1979). Among the existing various pyrazoline type derivatives, 1-acetyl-pyrazolines have been identified as one of the most promising scaffolds. In the field of medicinal chemistry, 1-acetyl-pyrazoline derivatives were found to display anticancer and anti-inflammatory activities. In addition, pyrazolines have played a crucial part in the development of theory in heterocyclic chemistry and also used extensively in organic synthesis (Klimova et al., 1999 & Bhaskarreddy et al., 1997). In continuation of our work on pyrazoline derivatives (Samshuddin et al., 2010, Fun et al., 2010, Yathirajan et al., 2007a,b, Butcher et al., 2007) and in view of the importance of these derivatives, the title compound (I) is synthesized and its crystal structure is reported here.

In (I), two chloro-substituted benzene rings are bonded to opposite ends of an acetyl substituted pyrazole ring in a slightly distorted envelope conformation (Fig. 1). The dihedral angle between the mean planes of the benzene (C4–C9) and chloro substituted benzene rings (C10–C15) with the pyrazole ring are 75.97 ° and 16.63 ° respectively. Two weak C—H···O intermolecular hydrogen bonds (Table 1) and π-π stacking interactions (Table 2) are observed which contribute to crystal packing stability (Fig. 2).

Related literature top

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 top

A mixture of (2E)-1,3-bis(4-chlorophenyl)prop-2-en-1-one (2.77 g, 0.01 mol) and hydrazine hydrate (0.5 ml, 0.01 mol) in 25 ml e thanol in presence of 2 ml glacial acetic acid was refluxed for 5 h (Fig. 3). The reaction mixture was cooled and poured into 50 ml ice-cold water. The precipitate was collected by filtration and purified by recrystallization from ethanol. The single-crystal was grown from DMF by slow evaporation method and yield of the compound was 84%.(m.p. 376 K). Analytical data: Found (Calculated): C %: 61.21(61.28); H%: 4.25 (4.23); N%: 8.35(8.41).

Structure description top

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).

Computing details top

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

Figures top

	Fig. 1. Molecular structure of (I), C₁₇H₁₄C₁₂N₂O, showing the atom labeling scheme and 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the title compound, (I), viewed down the a axis.
	Fig. 3. Reaction scheme of (I).

1-[3,5-Bis(4-chlorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone top

Crystal data top

C₁₇H₁₄Cl₂N₂O	F(000) = 688
M_r = 333.20	D_x = 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

Data collection top

Bruker APEXII CCD diffractometer	4809 independent reflections
Radiation source: fine-focus sealed tube	4141 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 31.3°, θ_min = 1.9°
Absorption correction: multi-scan (APEX2; Bruker, 2008)	h = −8→8
T_min = 0.803, T_max = 0.917	k = −18→18
18906 measured reflections	l = −28→28

Refinement top

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(F_o²) + (0.0475P)²] where P = (F_o² + 2F_c²)/3
4809 reflections	(Δ/σ)_max = 0.001
200 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₇H₁₄Cl₂N₂O	V = 1563.6 (4) Å³
M_r = 333.20	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.0716 (9) Å	µ = 0.42 mm⁻¹
b = 13.160 (2) Å	T = 100 K
c = 19.782 (3) Å	0.55 × 0.38 × 0.21 mm
β = 98.412 (2)°

Data collection top

Bruker APEXII CCD diffractometer	4809 independent reflections
Absorption correction: multi-scan (APEX2; Bruker, 2008)	4141 reflections with I > 2σ(I)
T_min = 0.803, T_max = 0.917	R_int = 0.026
18906 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.44	Δρ_max = 0.39 e Å⁻³
4809 reflections	Δρ_min = −0.26 e Å⁻³
200 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1/2, y−1/2, −z+1/2; (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₄Cl₂N₂O
M_r	333.20
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	6.0716 (9), 13.160 (2), 19.782 (3)
β (°)	98.412 (2)
V (Å³)	1563.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.42
Crystal size (mm)	0.55 × 0.38 × 0.21

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (APEX2; Bruker, 2008)
T_min, T_max	0.803, 0.917
No. of measured, independent and observed [I > 2σ(I)] reflections	18906, 4809, 4141
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.731

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.111, 1.44
No. of reflections	4809
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.26

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+1/2, y−1/2, −z+1/2; (ii) x−1, y, z.

Cg···Cg π stacking interactions, top

Cg1 is the centroid of the ring N1/N2/C1/C2/C3, Cg2 is the centroid of the ring C4–C9 and Cg3 is the centroid of the ring C10–C125.

	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)

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

Acknowledgements

JPJ thanks Dr Matthias Zeller and the YSU Department of Chemistry for their assistance with the data collection. The diffractometer was funded by NSF grant 0087210, by Ohio Board of Regents grant CAP-491, and by YSU. CSC thanks the University of Mysore for research facilities and HSY thanks University of Mysore for sabbatical leave.

References

Amir, M., Kumar, H. & Khan, S. A. (2008). Bioorg. Med. Chem. Lett. 18, 918–922. Web of Science CrossRef PubMed CAS Google Scholar
Anuradha, N., Thiruvalluvar, A., Mahalinga, M. & Butcher, R. J. (2008). Acta Cryst. E64, o2160. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bhaskarreddy, D., Chandrasekhar, B. N., Padmavathi, V. & Sumathi, R. P. (1997). Synthesis, 3, 491–494. Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA Google Scholar
Butcher, R. J., Jasinski, J. P., Prasad, D. J., Narayana, B. & Yathirajan, H. S. (2007). Acta Cryst. E63, o4005–o4006. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010). Acta Cryst. E66, o582–o583. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Hes, R. V., Wellinga, K. & Grosscurt, A. C. (1978). J. Agric. Food Chem. 26, 915–918. Google Scholar
Jian, F.-F. & Wang, J. (2006). Acta Cryst. E62, o5303–o5304. Web of Science CSD CrossRef IUCr Journals Google Scholar
Jian, F.-F., Wang, J. & Xiao, H.-L. (2006). Acta Cryst. E62, o4771–o4772. Web of Science CSD CrossRef IUCr Journals Google Scholar
Klimova, E. I., Marcos, M., Klimova, T. B., Cecilio, A. T., Ruben, A. T. & Lena, R. R. (1999). J. Organomet. Chem. 585, 106–111. Web of Science CSD CrossRef CAS Google Scholar
Lu, Z.-K., Diao, H.-L., Li, S. & He, B. (2008). Acta Cryst. E64, o1638. Web of Science CSD CrossRef IUCr Journals Google Scholar
Manna, F., Chimenti, F., Fioravanti, R., Bolasco, A., Secci, D., Chimenti, P., Ferlini, C. & Scambia, G. (2005). Bioorg. Med. Chem. Lett. 15, 4632–4635. Web of Science CrossRef PubMed CAS Google Scholar
Regaila, H. A., El-Bayonk, A. K. & Hammad, M. (1979). Egypt. J. Chem. 20, 197–202. Google Scholar
Samshuddin, S., Narayana, B., Yathirajan, H. S., Safwan, A. P. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o1279–o1280. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, S.-F., Zhu, W., Yang, X. & Zhou, L.-J. (2005). Acta Cryst. E61, o3985–o3986. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yathirajan, H. S., Bindya, S., Sarojini, B. K., Narayana, B. & Bolte, M. (2007a). Acta Cryst. E63, o2718. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yathirajan, H. S., Bindya, S., Sarojini, B. K., Narayana, B. & Bolte, M. (2007b). Acta Cryst. E63, o2566. Web of Science CSD CrossRef IUCr Journals Google Scholar