(2E)-1-(4-Amino­phen­yl)-3-(2,4-dichloro­phen­yl)prop-2-en-1-one

Singh, S.; Singh, M.K.; Agarwal, A.; Hussain, F.; Awasthi, S.K.

doi:10.1107/S1600536811020460

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Pages o1616-o1617

doi:10.1107/S1600536811020460

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(2E)-1-(4-Aminophenyl)-3-(2,4-dichlorophenyl)prop-2-en-1-one

Shailja Singh,^a Manavendra K. Singh,^b Alka Agarwal,^b Firasat Hussain ^c and Satish K. Awasthi ^a ^*

^aChemical Biology Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India, ^bDepartment of Medicinal Chemistry, Institute of Medical Sciences, Banaras Hindu University, Varanasi 225 001, Uttar Pradesh, India, and ^cNanoscience and Nanotechnology, Department of Chemistry, University of Delhi, Delhi 110 007, India
^*Correspondence e-mail: awasthisatish@yahoo.com

(Received 22 April 2011; accepted 28 May 2011; online 11 June 2011)

The title compound, C₁₅H₁₁Cl₂NO, is approximately planar (r.m.s. deviation = 0.062 Å) and contains a single C=C double bond in a trans (E) configuration. The crystal packing is stabilized by intermolecular N—H⋯N and N—H⋯O intermolecular hydrogen bonding.

Related literature

For related flavonoids, see: Bargellini & Marini-Bettolo (1940 ). For isoflavonoids, see: Nógrádi & Szöllösy (1996 ). For the biological activities of chalcones, see: Go et al. (2005 ); Hans et al. (2010 ); Trivedi et al. (2007 ); Nielsen et al. (2004 ). For antimalarial activity, see: Mishra et al. (2008 ). For antifilarial activity, see: Awasthi, Mishra, Dixit et al. (2009 ). For other chalcone crystal structures and small molecules, see: Fun et al. (2008 ); Li et al. (2009 ); Singh et al. (2011 ). For the synthesis, see: Migrdichian (1957 ); Awasthi, Mishra, Kumar et al. (2009 ). For intermolecular N—H⋯N and N—H⋯O hydrogen bonding, see: Fonar et al. (2001 ).

Experimental

Crystal data

C₁₅H₁₁Cl₂NO
M_r = 292.15
Monoclinic, P 2₁ /c
a = 22.771 (2) Å
b = 3.9889 (5) Å
c = 14.7848 (18) Å
β = 92.401 (12)°
V = 1341.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.47 mm⁻¹
T = 293 K
0.23 × 0.11 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.597, T_max = 1.000
5765 measured reflections
2625 independent reflections
1733 reflections with I > 2σ(I)
R_int = 0.047
Standard reflections: 0

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.159
S = 0.98
2625 reflections
216 parameters
All H-atom parameters refined
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1ⁱ	0.78 (3)	2.210	2.977 (4)	171 (3)
N1—H2N1⋯N1ⁱⁱ	0.76 (4)	2.469	3.134 (5)	147 (4)
Symmetry codes: (i) $[x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: 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: Mercury (Macrae et al., 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811020460/zj2011sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811020460/zj2011Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811020460/zj2011Isup3.cml

checkCIF report

Comment top

Chalcones (trans-1,3-diphenyl-2-propen-1-ones) are precursor of various natural products such as flavonoids (Bargellini & Marini-Bettolo, 1940), isoflavanoids (Nógrádi & Szöllösy, 1996) and key intermediates for synthesis of various heterocyclic scaffolds. Chalcone consists of two aromatic rings joined together by a three carbon α, β-unsaturated carbonyl system (Figure 1). These compounds have broad range of biological activities such as anticancer (Go et al., 2005), antimalarial activity (Mishra et al. 2008), anti-TB activity (Hans et al. 2010), antiviral (Trivedi et al., 2007), antibacterial (Nielsen et al., 2004) and more recently antifilarial activity (Awasthi, Mishra, Dixit et al. 2009) etc. Further, SAR on substituted chalcones reveal that presence of α, β-unsaturated ketone is critical for activity in which double bond is in a trans (E)-configuration (Li et al., 2009). The crystal structures of few substituted chalcones have been recently reported (Fun et al., 2008; Li et al., 2009). As a part of our ongoing research work on antimicrobial activities of substituted chalcones and crystal structure analysis of small molecules (Singh et al., 2011), we further explored the possibility of characterization of chalcone in the solid state. We crystallized substituted chalcone (2E)-1-(4-aminophenyl)-4-(2,4-dichlorophenyl) but-2-en-1-one,in the mixture of methanol and acetone at room temperature. In this paper, we report the single-crystal X-ray structure of the title compound and possible role of hydrogen bonding in the structure stabilization. The crystal packing is stabilized by intermolecular hydrogen bonding between N1-H2N1···N1 and N1-H1N1···O1(Fonar et al., 2001).as shown in packing diagram along b axis(figure 2, table 1).The torsion angle between atom C7—C8 - C9—C10 is 177.8 (3)°. The aminophenyl ring, dichlorophenyl ring and central ketone group are in the same plane, thus molecule is planer. The CCDC No. of the crystal is 797089.

Related literature top

For related flavonoids, see: Bargellini & Marini-Bettolo (1940). For isoflavonoids, see: Nógrádi & Szöllösy (1996). For biological activities of chalcones, see: Go et al. (2005); Hans et al. (2010); Trivedi et al. (2007); Nielsen et al. (2004). For antimalarial activity, see: Mishra et al. (2008). For antifilarial activity, see: Awasthi, Mishra, Dixit et al. (2009). For other chalcone crystal structures and small molecules, see: Fun et al. (2008); Li et al. (2009). Singh et al. (2011). For synthesis, see: Migrdichian (1957); Awasthi, Mishra, Kumar et al. (2009). For intermolecular hydrogen bonding between N—H···N and N—H···O, see: Fonar et al. (2001).

Experimental top

The synthesis of the title compound was carried out according to the published procedure (Migrdichian 1957; Awasthi, Mishra, Kumar et al., 2009). Briefly, an aqueous solution of sodium hydroxide (10%, 10 ml) was added to a solution of acetlylated 4-aminoacetophenone (1.77 g m, 10 mmol) and 2, 4-dichlorobenzaldehyde (1.73 g m, 10 mmol) in minimum amount of methanol (3–5 ml) at ice cooled flask. The reaction mixture was allowed to draw closer to room temperature and stirred for 18–20 hrs yielded a yellow solid. The completion of the reaction was monitored by thin layer chromatography. After completion of the reaction, the mixture was neutralized with 10% hydrochloric acid in water. The acetyl group was removed by refluxing with HCl/C₂H₅OH for 4hrs. The product was recrystallized from dry methanol and acetone in 1:1 ratio. After few weeks, light yellow single crystals were obtained. Yield 70%. R_f = 0.64 (CHCl₃: MeOH, 99:1). MS (Macromass G) m/z = 292.16 (M⁺). Elemental analysis (Perkin Elmer): Calcd. for C₁₅ H₁₁ Cl₂ NO: C 61.67, H 3.79, Cl 24.26, N 4.79, O 5.48%. Found C 61.70, H 3.81, Cl 24.23, N 4.83, O 5.44%. IR (Perkin Elmer Fourier transform Spectrometer with KBr pellets (cm^-1): 3462.18–3369.75 (–NH₂), 2925.42- 2851.54 (aromatic), 1704.23 (C=O in conjugation C=C), 1656.19 (C=C str aromatic), 1584.94 (C=C str in conjugation CO—C=C), 1269.49 (C—N str), 1018.68–1105.40 (C—O—C str), C—Cl (867.02–814.49). ¹³C-NMR (CDCl₃, 300 MHz): δ 186.66, 152.16, 136.54, 135.27, 135.13, 131.78, 130.75, 130.22, 129.38, 128.07, 127.03, 126.46, 124.75, 113.20, 113.00. ¹HNMR (Brucker AMX, 300 MHz, CDCl₃): δ 4. 196 (s, 2H, NH₂), δ 6.7 (d, 2H, H₂ and H₆, J = 8.7 Hz), δ 7.92 (d, 2H, H₃ and H₅, J = 8.4 Hz), δ 7.46 (d, 1H, H_α, J = 15.6 Hz), δ 8.06 (d, 1H, H_β, J = 15.6 Hz), δ 7.463 (s, 1H, H'₃), δ 7.29 (d, 1H, H'₅, J = 6.9 Hz), δ 7.67 (d, 1H, H'₆, J = 8.4 Hz).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. ORTEP diagram of the molecule with thermal ellipsoids drawn at 50% probability level Color code: White: C; red: O; blue: N; white: H; Green: Cl; Green: F
	Fig. 2. Packing diagram of molecule viewed through b plane showing Intermolecular hydrogen bonding.
	Fig. 3. The formation of the title compound.

(2E)-1-(4-Aminophenyl)-3-(2,4-dichlorophenyl)prop-2-en-1-one top

Crystal data top

C₁₅H₁₁Cl₂NO	F(000) = 600
M_r = 292.15	D_x = 1.446 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1458 reflections
a = 22.771 (2) Å	θ = 3.0–29.0°
b = 3.9889 (5) Å	µ = 0.47 mm⁻¹
c = 14.7848 (18) Å	T = 293 K
β = 92.401 (12)°	Rod, yellow
V = 1341.7 (3) Å³	0.23 × 0.11 × 0.08 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	2625 independent reflections
Radiation source: fine-focus sealed tube	1733 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
ω scans	θ_max = 26.0°, θ_min = 3.2°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −25→28
T_min = 0.597, T_max = 1.000	k = −3→4
5765 measured reflections	l = −17→18

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	All H-atom parameters refined
S = 0.98	w = 1/[σ²(F_o²) + (0.0919P)²] where P = (F_o² + 2F_c²)/3
2625 reflections	(Δ/σ)_max = 0.003
216 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₅H₁₁Cl₂NO	V = 1341.7 (3) Å³
M_r = 292.15	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 22.771 (2) Å	µ = 0.47 mm⁻¹
b = 3.9889 (5) Å	T = 293 K
c = 14.7848 (18) Å	0.23 × 0.11 × 0.08 mm
β = 92.401 (12)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	2625 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	1733 reflections with I > 2σ(I)
T_min = 0.597, T_max = 1.000	R_int = 0.047
5765 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.159	All H-atom parameters refined
S = 0.98	Δρ_max = 0.33 e Å⁻³
2625 reflections	Δρ_min = −0.29 e Å⁻³
216 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
C1	0.85377 (14)	0.5099 (8)	0.5485 (2)	0.0466 (8)
C2	0.91136 (15)	0.6162 (9)	0.5505 (2)	0.0496 (8)
C3	0.93472 (13)	0.7698 (8)	0.6273 (2)	0.0454 (8)
C4	0.90165 (14)	0.8197 (8)	0.7010 (2)	0.0465 (8)
C5	0.84351 (14)	0.7060 (8)	0.6984 (2)	0.0440 (7)
C6	0.81845 (12)	0.5488 (7)	0.62200 (19)	0.0376 (7)
C7	0.75725 (13)	0.4285 (8)	0.6200 (2)	0.0434 (8)
C8	0.72868 (14)	0.2879 (9)	0.5517 (2)	0.0452 (8)
C9	0.66735 (13)	0.1629 (7)	0.5571 (2)	0.0403 (7)
C10	0.63905 (12)	−0.0047 (7)	0.47851 (18)	0.0334 (6)
C11	0.66507 (13)	−0.0353 (8)	0.3948 (2)	0.0408 (7)
C12	0.63760 (13)	−0.1948 (8)	0.3229 (2)	0.0421 (7)
C13	0.58122 (12)	−0.3296 (7)	0.33087 (19)	0.0344 (7)
C14	0.55456 (13)	−0.2959 (8)	0.4125 (2)	0.0384 (7)
C15	0.58231 (13)	−0.1377 (8)	0.4847 (2)	0.0392 (7)
N1	0.55305 (14)	−0.4825 (8)	0.2576 (2)	0.0443 (7)
O1	0.64210 (10)	0.1991 (6)	0.62783 (15)	0.0604 (7)
Cl1	1.00725 (4)	0.9059 (2)	0.63141 (7)	0.0648 (3)
Cl2	0.80366 (5)	0.7782 (3)	0.79390 (6)	0.0786 (4)
H1	0.8413 (15)	0.404 (8)	0.482 (2)	0.057 (9)*
H1N1	0.5731 (15)	−0.545 (9)	0.220 (2)	0.041 (10)*
H2	0.9359 (16)	0.602 (9)	0.509 (2)	0.058 (10)*
H2N1	0.5329 (19)	−0.618 (10)	0.275 (3)	0.067 (15)*
H4	0.9136 (16)	0.923 (9)	0.749 (3)	0.065 (11)*
H7	0.7369 (18)	0.430 (10)	0.674 (3)	0.078 (12)*
H8	0.7462 (17)	0.234 (9)	0.505 (3)	0.065 (12)*
H11	0.7039 (18)	0.068 (10)	0.384 (3)	0.075 (11)*
H12	0.6574 (14)	−0.213 (7)	0.271 (2)	0.042 (8)*
H14	0.5245 (17)	−0.397 (9)	0.422 (2)	0.060 (11)*
H15	0.5611 (13)	−0.119 (7)	0.537 (2)	0.038 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0408 (17)	0.055 (2)	0.0431 (18)	−0.0017 (16)	−0.0039 (14)	−0.0028 (16)
C2	0.0424 (18)	0.056 (2)	0.051 (2)	−0.0029 (16)	0.0079 (16)	−0.0013 (17)
C3	0.0372 (15)	0.0416 (17)	0.056 (2)	−0.0002 (14)	−0.0094 (15)	0.0068 (15)
C4	0.0461 (18)	0.0424 (19)	0.050 (2)	−0.0059 (15)	−0.0119 (16)	−0.0010 (16)
C5	0.0446 (17)	0.0468 (18)	0.0400 (16)	−0.0010 (15)	−0.0043 (14)	−0.0017 (14)
C6	0.0349 (15)	0.0369 (16)	0.0403 (16)	−0.0002 (13)	−0.0054 (13)	0.0005 (13)
C7	0.0380 (16)	0.0498 (19)	0.0424 (17)	−0.0030 (15)	−0.0007 (14)	−0.0002 (15)
C8	0.0368 (16)	0.057 (2)	0.0421 (18)	−0.0077 (15)	0.0036 (15)	−0.0031 (16)
C9	0.0370 (15)	0.0422 (18)	0.0414 (17)	0.0001 (14)	−0.0004 (14)	0.0033 (14)
C10	0.0268 (13)	0.0373 (16)	0.0361 (15)	0.0007 (12)	−0.0003 (11)	0.0033 (12)
C11	0.0286 (14)	0.0513 (19)	0.0426 (17)	−0.0049 (14)	0.0017 (13)	0.0028 (15)
C12	0.0338 (15)	0.057 (2)	0.0362 (16)	0.0001 (15)	0.0057 (13)	−0.0007 (15)
C13	0.0303 (14)	0.0349 (16)	0.0374 (15)	0.0042 (12)	−0.0043 (12)	0.0009 (12)
C14	0.0275 (15)	0.0425 (18)	0.0452 (17)	−0.0054 (14)	0.0007 (13)	0.0031 (14)
C15	0.0333 (15)	0.0470 (19)	0.0378 (16)	0.0013 (14)	0.0068 (13)	0.0016 (14)
N1	0.0372 (15)	0.054 (2)	0.0409 (16)	−0.0038 (15)	−0.0023 (13)	−0.0097 (15)
O1	0.0515 (13)	0.0868 (19)	0.0436 (13)	−0.0177 (13)	0.0096 (11)	−0.0133 (12)
Cl1	0.0387 (5)	0.0691 (6)	0.0857 (7)	−0.0114 (4)	−0.0079 (4)	0.0039 (5)
Cl2	0.0705 (6)	0.1094 (9)	0.0565 (6)	−0.0218 (6)	0.0104 (5)	−0.0299 (6)

Geometric parameters (Å, º) top

C1—C2	1.377 (5)	C9—O1	1.223 (4)
C1—C6	1.388 (4)	C9—C10	1.466 (4)
C1—H1	1.10 (3)	C10—C11	1.399 (4)
C2—C3	1.377 (5)	C10—C15	1.403 (4)
C2—H2	0.85 (4)	C11—C12	1.368 (4)
C3—C4	1.365 (5)	C11—H11	0.99 (4)
C3—Cl1	1.737 (3)	C12—C13	1.401 (4)
C4—C5	1.399 (5)	C12—H12	0.91 (3)
C4—H4	0.86 (4)	C13—C14	1.381 (4)
C5—C6	1.393 (4)	C13—N1	1.378 (4)
C5—Cl2	1.734 (3)	C14—C15	1.371 (4)
C6—C7	1.473 (4)	C14—H14	0.81 (4)
C7—C8	1.305 (4)	C15—H15	0.93 (3)
C7—H7	0.94 (4)	N1—H1N1	0.78 (4)
C8—C9	1.488 (4)	N1—H2N1	0.76 (4)
C8—H8	0.84 (4)

C2—C1—C6	122.1 (3)	O1—C9—C10	121.7 (3)
C2—C1—H1	110.2 (18)	O1—C9—C8	118.8 (3)
C6—C1—H1	127.6 (18)	C10—C9—C8	119.5 (3)
C3—C2—C1	119.3 (3)	C11—C10—C15	116.7 (3)
C3—C2—H2	113 (2)	C11—C10—C9	123.5 (3)
C1—C2—H2	128 (2)	C15—C10—C9	119.7 (3)
C4—C3—C2	121.1 (3)	C12—C11—C10	122.1 (3)
C4—C3—Cl1	118.8 (2)	C12—C11—H11	117 (2)
C2—C3—Cl1	120.1 (3)	C10—C11—H11	121 (2)
C3—C4—C5	119.0 (3)	C11—C12—C13	120.2 (3)
C3—C4—H4	125 (3)	C11—C12—H12	117.7 (19)
C5—C4—H4	116 (3)	C13—C12—H12	122.0 (19)
C6—C5—C4	121.5 (3)	C14—C13—N1	121.6 (3)
C6—C5—Cl2	121.6 (2)	C14—C13—C12	118.3 (3)
C4—C5—Cl2	116.8 (2)	N1—C13—C12	120.1 (3)
C1—C6—C5	117.0 (3)	C15—C14—C13	121.4 (3)
C1—C6—C7	121.8 (3)	C15—C14—H14	117 (3)
C5—C6—C7	121.2 (3)	C13—C14—H14	120 (3)
C8—C7—C6	126.6 (3)	C14—C15—C10	121.2 (3)
C8—C7—H7	114 (2)	C14—C15—H15	116.4 (18)
C6—C7—H7	119 (2)	C10—C15—H15	122.4 (18)
C7—C8—C9	122.8 (3)	C13—N1—H1N1	116 (2)
C7—C8—H8	120 (3)	C13—N1—H2N1	109 (3)
C9—C8—H8	116 (3)	H1N1—N1—H2N1	113 (4)

C6—C1—C2—C3	−0.8 (5)	C7—C8—C9—O1	1.5 (5)
C1—C2—C3—C4	−0.4 (5)	C7—C8—C9—C10	−177.5 (3)
C1—C2—C3—Cl1	180.0 (2)	O1—C9—C10—C11	176.4 (3)
C2—C3—C4—C5	1.3 (5)	C8—C9—C10—C11	−4.6 (4)
Cl1—C3—C4—C5	−179.1 (2)	O1—C9—C10—C15	−2.1 (4)
C3—C4—C5—C6	−1.2 (5)	C8—C9—C10—C15	176.8 (3)
C3—C4—C5—Cl2	−179.8 (2)	C15—C10—C11—C12	−1.8 (4)
C2—C1—C6—C5	0.9 (5)	C9—C10—C11—C12	179.7 (3)
C2—C1—C6—C7	−178.8 (3)	C10—C11—C12—C13	1.0 (5)
C4—C5—C6—C1	0.1 (5)	C11—C12—C13—C14	0.2 (4)
Cl2—C5—C6—C1	178.6 (2)	C11—C12—C13—N1	178.3 (3)
C4—C5—C6—C7	179.7 (3)	N1—C13—C14—C15	−178.7 (3)
Cl2—C5—C6—C7	−1.7 (4)	C12—C13—C14—C15	−0.6 (4)
C1—C6—C7—C8	−2.6 (5)	C13—C14—C15—C10	−0.2 (5)
C5—C6—C7—C8	177.8 (3)	C11—C10—C15—C14	1.4 (4)
C6—C7—C8—C9	177.8 (3)	C9—C10—C15—C14	180.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ⁱ	0.78 (3)	2.210	2.977 (4)	171 (3)
N1—H2N1···N1ⁱⁱ	0.76 (4)	2.469	3.134 (5)	147 (4)

Symmetry codes: (i) x, −y−1/2, z+1/2; (ii) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₁Cl₂NO
M_r	292.15
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	22.771 (2), 3.9889 (5), 14.7848 (18)
β (°)	92.401 (12)
V (Å³)	1341.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.47
Crystal size (mm)	0.23 × 0.11 × 0.08

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.597, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	5765, 2625, 1733
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.159, 0.98
No. of reflections	2625
No. of parameters	216
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.29

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ⁱ	0.78 (3)	2.210	2.977 (4)	171 (3)
N1—H2N1···N1ⁱⁱ	0.76 (4)	2.469	3.134 (5)	147 (4)

Symmetry codes: (i) x, −y−1/2, z+1/2; (ii) −x+1, y−1/2, −z+1/2.

Acknowledgements

SKA is thankful to the University Grants Commission (UGC) [scheme F. No. 37-410/2009(SR)] and the University of Delhi, India, for financial assistance. The authors are highly thankful to the University Sophisticated Instrument Center (USIC), University of Delhi, India, for providing the single-crystal X-ray diffractometer facility.

References

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