(E)-3-(2-Chloro-6-methyl-3-quinol­yl)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)prop-2-en-1-one

Rizvi, S.U.F.; Siddiqui, H.L.; Hussain, T.; Azam, M.; Parvez, M.

doi:10.1107/S1600536810007464

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o744

doi:10.1107/S1600536810007464

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(E)-3-(2-Chloro-6-methyl-3-quinolyl)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)prop-2-en-1-one

Syed Umar Farooq Rizvi,^a Hamid Latif Siddiqui,^a ^* Tanvir Hussain,^a Muhammad Azam ^b and Masood Parvez ^c

^aInstitute of Chemistry, University of the Punjab, Lahore 54590, Pakistan, ^bInstitute of Biochemistry, University of Balouchistan, Quetta 7800, Pakistan, and ^cDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
^*Correspondence e-mail: drhamidlatif@yahoo.com

(Received 23 February 2010; accepted 26 February 2010; online 3 March 2010)

In the title molecule, C₂₁H₁₆ClNO₃, the quinoline and benzene rings are inclined at 56.96 (6)° with respect to each other and the dioxine ring is in a twist-chair conformation. The structure is devoid of any classical hydrogen bonds. Rather weak intermolecular hydrogen-bonding interactions of the types C—H⋯N and C—H⋯O are present, consolidating the crystal structure.

Related literature

For background to chalcones, see: Mishra et al. (2008 ); Xia et al. (2000 ); Vaya et al. (1997 ); Bhakuni & Chaturvedi (1984 ); Nielsen et al. (2005 ); Wu et al. (2003 ). For comparison bond lengths, see: Allen et al. (1987 ). For a related structure, see: Rizvi et al. (2010 ) For the preparation of the precursor 2-chloro-6-methyl-3-formylquinoline, see: Meth-Cohn et al. (1981 ).

Experimental

Crystal data

C₂₁H₁₆ClNO₃
M_r = 365.80
Monoclinic, P 2₁ /c
a = 6.370 (3) Å
b = 38.735 (9) Å
c = 7.409 (4) Å
β = 114.93 (2)°
V = 1657.8 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 173 K
0.18 × 0.16 × 0.14 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ) T_min = 0.956, T_max = 0.966
6971 measured reflections
2933 independent reflections
2256 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.091
S = 1.03
2933 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯N1ⁱ	0.95	2.57	3.514 (3)	170
C18—H18⋯O2ⁱⁱ	0.95	2.53	3.266 (3)	134
C21—H21A⋯O1ⁱⁱⁱ	0.99	2.53	3.406 (3)	147
Symmetry codes: (i) -x+2, -y, -z+2; (ii) x+1, y, z; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810007464/si2245sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810007464/si2245Isup2.hkl

checkCIF report

Comment top

α,β-Unsaturated ketones or 1,3-diaryl-2-propen-1-ones, commonly known as chalcones, have already been recognized as antimalarial (Mishra et al., 2008), antitumor (Xia et al., 2000), antioxidant (Vaya et al., 1997), antifungal (Bhakuni & Chaturvedi, 1984), antibacterial (Nielsen et al., 2005), and anti-AIDS agents (Wu et al., 2003). Continuing our investigations in this important area (Rizvi et al., 2010) we now report the synthesis and crystal structure of a new chalcone, containing quinolyl ring system, (2E)-3-(2-chloro-6-methylquinolin-3-yl)-1-(2,3-dihydro-1,4-benzodioxin-6-yl) prop-2-en-1-one, in this article. A series of chalcones related to the title compound is under investigation for their biological activities in our laboratory.

The title molecule is presented in Fig. 1. The bond distances (Allen et al., 1987) and angles are as expected and agree with the corresponding bond distances and angles reported in a closely related compound (Rizvi et al., 2010). The least-square planes of the quinoline and phenyl rings defined by atoms N1/C1—C9 and C14—C19, respectively, are inclined at 56.95 (6)° with respect to each other. The dioxine ring is in a twist-chair conformation with C20 and C21 atoms 0.425 (3) and 0.307 (3) Å on the opposite sides of the plane formed by the remining ring atoms. The structure is devoid of any classical hydrogen bonds. However, short intramolecular interactions involving Cl1 and O1 and rather weak hydrogen bonding inter-molecular interactions of the types C—H···N and C—H···O are present consolidating the crystal packing; details have been provided in Table 1.

Related literature top

For background to chalcones, see: Mishra et al. (2008); Xia et al. (2000); Vaya et al. (1997); Bhakuni & Chaturvedi (1984); Nielsen et al. (2005; Wu et al. (2003). For comparison bond lengthet al.987 s, see: Allen et al. (1987). For a related structure, see: Rizvi et al. (2010) For the preparation of the precursor 2-chloro-6-methyl-3-formylquinoline, see: Meth-Cohn et al. (1981).

Experimental top

The precursor 2-chloro-6-methyl-3-formylquinoline was prepared by reported method (Meth-Cohn et al., 1981). A mixture of 2-chloro-6-methyl-3-formylquinoline (2.055 g, 10 mmol) and 6-acetyl-1,4-benzodioxane (1.7819 g, 10 mmol) in methanol (50 ml) was stirred at room temperature followed by dropwise addition of aq. NaOH (4 ml, 10%). The stirring was continued (2 h) and the reaction mixture was kept at 273 K (24 h). Then it was poured on to ice-cold water (200 ml). The precipitates were collected by filtration, washed with cold water followed by cold MeOH. The resulting chalcone was recrystallised from CHCl₃ to obtain the title compound as yellow crystalline product, (yield 2.76 g, 7.55 mmol, 75.5%), (m.p. 458-460 K).

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. ORTEP-3 (Farrugia, 1997) drawing of (I) with displacement ellipsoids plotted at 50% probability level.

(E)-3-(2-Chloro-6-methyl-3-quinolyl)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)prop-2-en-1-one top

Crystal data top

C₂₁H₁₆ClNO₃	F(000) = 760
M_r = 365.80	D_x = 1.466 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6971 reflections
a = 6.370 (3) Å	θ = 3.6–25.3°
b = 38.735 (9) Å	µ = 0.25 mm⁻¹
c = 7.409 (4) Å	T = 173 K
β = 114.93 (2)°	Prism, colorless
V = 1657.8 (12) Å³	0.18 × 0.16 × 0.14 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	2933 independent reflections
Radiation source: fine-focus sealed tube	2256 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ω and ϕ scans	θ_max = 25.4°, θ_min = 3.6°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −7→7
T_min = 0.956, T_max = 0.966	k = −46→45
6971 measured reflections	l = −8→8

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: difference Fourier map
wR(F²) = 0.091	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0323P)² + 0.8409P] where P = (F_o² + 2F_c²)/3
2933 reflections	(Δ/σ)_max = 0.001
236 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₁H₁₆ClNO₃	V = 1657.8 (12) Å³
M_r = 365.80	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.370 (3) Å	µ = 0.25 mm⁻¹
b = 38.735 (9) Å	T = 173 K
c = 7.409 (4) Å	0.18 × 0.16 × 0.14 mm
β = 114.93 (2)°

Data collection top

Nonius KappaCCD diffractometer	2933 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	2256 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.966	R_int = 0.037
6971 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 1.03	Δρ_max = 0.19 e Å⁻³
2933 reflections	Δρ_min = −0.23 e Å⁻³
236 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.61049 (9)	0.077424 (13)	1.07582 (8)	0.03394 (16)
O1	0.1834 (2)	0.18022 (3)	0.7158 (2)	0.0336 (4)
O2	0.0375 (2)	0.30663 (3)	0.6559 (2)	0.0320 (4)
O3	0.4801 (2)	0.33735 (3)	0.7522 (2)	0.0338 (4)
N1	0.8742 (3)	0.05188 (4)	0.9228 (2)	0.0267 (4)
C1	0.9871 (3)	0.05159 (5)	0.8010 (3)	0.0246 (4)
C2	1.1233 (3)	0.02252 (5)	0.8050 (3)	0.0287 (5)
H2	1.1381	0.0039	0.8932	0.034*
C3	1.2333 (3)	0.02116 (5)	0.6821 (3)	0.0306 (5)
H3	1.3235	0.0014	0.6859	0.037*
C4	1.2168 (3)	0.04847 (5)	0.5487 (3)	0.0276 (5)
C5	1.0885 (3)	0.07697 (5)	0.5472 (3)	0.0269 (4)
H5	1.0790	0.0956	0.4605	0.032*
C6	0.9699 (3)	0.07956 (5)	0.6704 (3)	0.0243 (4)
C7	0.8272 (3)	0.10775 (5)	0.6683 (3)	0.0258 (4)
H7	0.8131	0.1269	0.5838	0.031*
C8	0.7085 (3)	0.10785 (5)	0.7868 (3)	0.0241 (4)
C9	0.7448 (3)	0.07847 (5)	0.9125 (3)	0.0255 (4)
C10	1.3379 (4)	0.04523 (6)	0.4128 (3)	0.0350 (5)
H10A	1.3123	0.0663	0.3328	0.042*
H10B	1.2757	0.0253	0.3246	0.042*
H10C	1.5042	0.0420	0.4928	0.042*
C11	0.5459 (3)	0.13523 (5)	0.7802 (3)	0.0261 (5)
H11	0.4158	0.1282	0.8025	0.031*
C12	0.5602 (3)	0.16871 (5)	0.7467 (3)	0.0268 (5)
H12	0.6904	0.1774	0.7302	0.032*
C13	0.3705 (3)	0.19247 (5)	0.7352 (3)	0.0259 (4)
C14	0.4061 (3)	0.23038 (5)	0.7428 (3)	0.0222 (4)
C15	0.2138 (3)	0.25160 (5)	0.6999 (3)	0.0239 (4)
H15	0.0667	0.2415	0.6683	0.029*
C16	0.2342 (3)	0.28706 (5)	0.7026 (3)	0.0235 (4)
C17	0.4504 (3)	0.30212 (5)	0.7508 (3)	0.0252 (4)
C18	0.6434 (3)	0.28131 (5)	0.8000 (3)	0.0300 (5)
H18	0.7915	0.2916	0.8382	0.036*
C19	0.6226 (3)	0.24564 (5)	0.7942 (3)	0.0278 (5)
H19	0.7555	0.2316	0.8250	0.033*
C20	0.0868 (3)	0.34184 (5)	0.7204 (3)	0.0290 (5)
H20A	0.1447	0.3430	0.8670	0.035*
H20B	−0.0566	0.3558	0.6607	0.035*
C21	0.2653 (4)	0.35620 (5)	0.6590 (3)	0.0346 (5)
H21A	0.2077	0.3547	0.5125	0.041*
H21B	0.2925	0.3808	0.6974	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0392 (3)	0.0327 (3)	0.0351 (3)	0.0045 (2)	0.0207 (2)	0.0033 (2)
O1	0.0288 (8)	0.0239 (8)	0.0471 (9)	−0.0005 (6)	0.0150 (7)	0.0008 (6)
O2	0.0259 (7)	0.0194 (7)	0.0490 (9)	0.0032 (6)	0.0141 (7)	−0.0016 (6)
O3	0.0339 (8)	0.0204 (7)	0.0498 (9)	−0.0021 (6)	0.0202 (7)	0.0013 (7)
N1	0.0287 (9)	0.0218 (9)	0.0289 (9)	0.0011 (7)	0.0113 (8)	0.0026 (7)
C1	0.0238 (10)	0.0200 (10)	0.0269 (11)	−0.0003 (8)	0.0077 (9)	−0.0001 (8)
C2	0.0314 (11)	0.0216 (10)	0.0333 (12)	0.0026 (8)	0.0138 (9)	0.0055 (9)
C3	0.0312 (11)	0.0228 (11)	0.0375 (12)	0.0034 (9)	0.0142 (10)	0.0004 (9)
C4	0.0267 (10)	0.0237 (11)	0.0323 (11)	−0.0023 (8)	0.0123 (9)	−0.0019 (9)
C5	0.0281 (10)	0.0220 (10)	0.0291 (11)	−0.0034 (8)	0.0106 (9)	0.0039 (8)
C6	0.0213 (9)	0.0199 (10)	0.0278 (11)	−0.0024 (8)	0.0066 (8)	−0.0018 (8)
C7	0.0270 (10)	0.0175 (10)	0.0289 (11)	−0.0025 (8)	0.0078 (9)	0.0030 (8)
C8	0.0232 (10)	0.0185 (10)	0.0263 (10)	−0.0018 (8)	0.0063 (8)	−0.0011 (8)
C9	0.0267 (10)	0.0224 (10)	0.0264 (10)	−0.0025 (8)	0.0102 (8)	−0.0015 (8)
C10	0.0375 (12)	0.0321 (12)	0.0404 (13)	−0.0001 (9)	0.0214 (11)	0.0003 (10)
C11	0.0246 (10)	0.0220 (11)	0.0278 (11)	0.0003 (8)	0.0072 (9)	−0.0027 (8)
C12	0.0265 (10)	0.0247 (11)	0.0282 (11)	0.0016 (8)	0.0104 (9)	−0.0012 (8)
C13	0.0267 (10)	0.0246 (11)	0.0234 (10)	−0.0003 (8)	0.0075 (9)	0.0014 (8)
C14	0.0258 (10)	0.0209 (10)	0.0206 (10)	0.0025 (8)	0.0103 (8)	0.0010 (8)
C15	0.0222 (10)	0.0228 (11)	0.0265 (10)	−0.0013 (8)	0.0101 (8)	0.0002 (8)
C16	0.0249 (10)	0.0219 (10)	0.0233 (10)	0.0024 (8)	0.0097 (8)	0.0006 (8)
C17	0.0312 (11)	0.0183 (10)	0.0271 (11)	−0.0010 (8)	0.0131 (9)	−0.0003 (8)
C18	0.0246 (10)	0.0279 (11)	0.0385 (12)	−0.0055 (9)	0.0144 (9)	−0.0022 (9)
C19	0.0234 (10)	0.0270 (11)	0.0341 (11)	0.0041 (8)	0.0130 (9)	0.0015 (9)
C20	0.0336 (11)	0.0204 (11)	0.0328 (11)	0.0040 (9)	0.0137 (9)	−0.0005 (9)
C21	0.0417 (13)	0.0219 (11)	0.0426 (13)	0.0055 (9)	0.0202 (11)	0.0044 (9)

Geometric parameters (Å, º) top

Cl1—C9	1.752 (2)	C10—H10A	0.9800
O1—C13	1.234 (2)	C10—H10B	0.9800
O2—C16	1.378 (2)	C10—H10C	0.9800
O2—C20	1.435 (2)	C11—C12	1.331 (3)
O3—C17	1.377 (2)	C11—H11	0.9500
O3—C21	1.444 (2)	C12—C13	1.492 (3)
N1—C9	1.301 (2)	C12—H12	0.9500
N1—C1	1.371 (3)	C13—C14	1.483 (3)
C1—C2	1.414 (3)	C14—C15	1.396 (3)
C1—C6	1.426 (3)	C14—C19	1.398 (3)
C2—C3	1.364 (3)	C15—C16	1.379 (3)
C2—H2	0.9500	C15—H15	0.9500
C3—C4	1.421 (3)	C16—C17	1.396 (3)
C3—H3	0.9500	C17—C18	1.385 (3)
C4—C5	1.371 (3)	C18—C19	1.387 (3)
C4—C10	1.509 (3)	C18—H18	0.9500
C5—C6	1.413 (3)	C19—H19	0.9500
C5—H5	0.9500	C20—C21	1.498 (3)
C6—C7	1.416 (3)	C20—H20A	0.9900
C7—C8	1.379 (3)	C20—H20B	0.9900
C7—H7	0.9500	C21—H21A	0.9900
C8—C9	1.426 (3)	C21—H21B	0.9900
C8—C11	1.469 (3)

C16—O2—C20	112.99 (15)	C8—C11—H11	116.3
C17—O3—C21	113.44 (15)	C11—C12—C13	119.61 (19)
C9—N1—C1	117.57 (16)	C11—C12—H12	120.2
N1—C1—C2	118.71 (17)	C13—C12—H12	120.2
N1—C1—C6	121.93 (17)	O1—C13—C14	120.65 (18)
C2—C1—C6	119.36 (18)	O1—C13—C12	119.25 (18)
C3—C2—C1	120.01 (18)	C14—C13—C12	120.09 (18)
C3—C2—H2	120.0	C15—C14—C19	118.90 (18)
C1—C2—H2	120.0	C15—C14—C13	117.97 (17)
C2—C3—C4	121.82 (19)	C19—C14—C13	123.12 (17)
C2—C3—H3	119.1	C16—C15—C14	121.01 (18)
C4—C3—H3	119.1	C16—C15—H15	119.5
C5—C4—C3	118.31 (19)	C14—C15—H15	119.5
C5—C4—C10	122.13 (18)	O2—C16—C15	118.31 (17)
C3—C4—C10	119.56 (18)	O2—C16—C17	121.94 (17)
C4—C5—C6	122.10 (18)	C15—C16—C17	119.75 (17)
C4—C5—H5	119.0	O3—C17—C18	118.09 (18)
C6—C5—H5	119.0	O3—C17—C16	122.24 (17)
C5—C6—C7	124.26 (18)	C18—C17—C16	119.67 (18)
C5—C6—C1	118.38 (17)	C17—C18—C19	120.62 (19)
C7—C6—C1	117.32 (18)	C17—C18—H18	119.7
C8—C7—C6	121.09 (17)	C19—C18—H18	119.7
C8—C7—H7	119.5	C18—C19—C14	120.00 (18)
C6—C7—H7	119.5	C18—C19—H19	120.0
C7—C8—C9	115.58 (17)	C14—C19—H19	120.0
C7—C8—C11	123.31 (17)	O2—C20—C21	109.83 (16)
C9—C8—C11	121.05 (18)	O2—C20—H20A	109.7
N1—C9—C8	126.48 (19)	C21—C20—H20A	109.7
N1—C9—Cl1	114.99 (15)	O2—C20—H20B	109.7
C8—C9—Cl1	118.51 (15)	C21—C20—H20B	109.7
C4—C10—H10A	109.5	H20A—C20—H20B	108.2
C4—C10—H10B	109.5	O3—C21—C20	110.74 (17)
H10A—C10—H10B	109.5	O3—C21—H21A	109.5
C4—C10—H10C	109.5	C20—C21—H21A	109.5
H10A—C10—H10C	109.5	O3—C21—H21B	109.5
H10B—C10—H10C	109.5	C20—C21—H21B	109.5
C12—C11—C8	127.38 (19)	H21A—C21—H21B	108.1
C12—C11—H11	116.3

C9—N1—C1—C2	−178.11 (17)	C8—C11—C12—C13	176.79 (18)
C9—N1—C1—C6	1.5 (3)	C11—C12—C13—O1	−14.8 (3)
N1—C1—C2—C3	178.47 (18)	C11—C12—C13—C14	166.44 (18)
C6—C1—C2—C3	−1.1 (3)	O1—C13—C14—C15	−8.8 (3)
C1—C2—C3—C4	0.3 (3)	C12—C13—C14—C15	169.95 (17)
C2—C3—C4—C5	0.9 (3)	O1—C13—C14—C19	170.08 (19)
C2—C3—C4—C10	−178.64 (19)	C12—C13—C14—C19	−11.2 (3)
C3—C4—C5—C6	−1.3 (3)	C19—C14—C15—C16	1.7 (3)
C10—C4—C5—C6	178.19 (18)	C13—C14—C15—C16	−179.44 (17)
C4—C5—C6—C7	−177.15 (18)	C20—O2—C16—C15	162.26 (17)
C4—C5—C6—C1	0.5 (3)	C20—O2—C16—C17	−18.1 (3)
N1—C1—C6—C5	−178.89 (17)	C14—C15—C16—O2	179.02 (17)
C2—C1—C6—C5	0.7 (3)	C14—C15—C16—C17	−0.6 (3)
N1—C1—C6—C7	−1.0 (3)	C21—O3—C17—C18	167.52 (18)
C2—C1—C6—C7	178.55 (17)	C21—O3—C17—C16	−12.7 (3)
C5—C6—C7—C8	177.13 (18)	O2—C16—C17—O3	−0.9 (3)
C1—C6—C7—C8	−0.6 (3)	C15—C16—C17—O3	178.76 (17)
C6—C7—C8—C9	1.6 (3)	O2—C16—C17—C18	178.86 (18)
C6—C7—C8—C11	−175.60 (17)	C15—C16—C17—C18	−1.5 (3)
C1—N1—C9—C8	−0.4 (3)	O3—C17—C18—C19	−177.65 (18)
C1—N1—C9—Cl1	−178.80 (13)	C16—C17—C18—C19	2.6 (3)
C7—C8—C9—N1	−1.2 (3)	C17—C18—C19—C14	−1.6 (3)
C11—C8—C9—N1	176.08 (18)	C15—C14—C19—C18	−0.6 (3)
C7—C8—C9—Cl1	177.23 (14)	C13—C14—C19—C18	−179.41 (18)
C11—C8—C9—Cl1	−5.5 (2)	C16—O2—C20—C21	48.1 (2)
C7—C8—C11—C12	−34.3 (3)	C17—O3—C21—C20	43.1 (2)
C9—C8—C11—C12	148.6 (2)	O2—C20—C21—O3	−62.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Cl1	0.95	2.72	3.036 (2)	100
C11—H11···O1	0.95	2.42	2.769 (2)	101
C2—H2···N1ⁱ	0.95	2.57	3.514 (3)	170
C18—H18···O2ⁱⁱ	0.95	2.53	3.266 (3)	134
C21—H21A···O1ⁱⁱⁱ	0.99	2.53	3.406 (3)	147

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₆ClNO₃
M_r	365.80
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	6.370 (3), 38.735 (9), 7.409 (4)
β (°)	114.93 (2)
V (Å³)	1657.8 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.18 × 0.16 × 0.14

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1997)
T_min, T_max	0.956, 0.966
No. of measured, independent and observed [I > 2σ(I)] reflections	6971, 2933, 2256
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.604

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.091, 1.03
No. of reflections	2933
No. of parameters	236
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.23

Computer programs: COLLECT (Hooft, 1998), DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Cl1	0.95	2.72	3.036 (2)	100
C11—H11···O1	0.95	2.42	2.769 (2)	101
C2—H2···N1ⁱ	0.95	2.57	3.514 (3)	170
C18—H18···O2ⁱⁱ	0.95	2.53	3.266 (3)	134
C21—H21A···O1ⁱⁱⁱ	0.99	2.53	3.406 (3)	147

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

Acknowledgements

The authors greatly appreciate financial support from the Higher Education Commission, Islamabad, and the Institute of Chemistry, University of the Punjab, Lahore.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bhakuni, D. S. & Chaturvedi, R. (1984). J. Nat. Prod. 47, 585–591. CrossRef CAS PubMed Web of Science Google Scholar
Blessing, R. H. (1997). J. Appl. Cryst. 30, 421–426. CrossRef CAS Web of Science IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hooft, R. (1998). COLLECT. Nonius B V, Delft, The Netherlands. Google Scholar
Meth-Cohn, O., Narine, B. & Tarnowski, B. (1981). J. Chem. Soc. Perkin Trans. 1, pp. 1520–1530. CrossRef Web of Science Google Scholar
Mishra, N., Arora, P., Kumar, B., Mishra, L. C., Bhattacharya, A., Awasthi, S. K. & Bhasin, V. K. (2008). Eur. J. Med. Chem. 43, 1530–1535. Web of Science CrossRef PubMed CAS Google Scholar
Nielsen, S. F., Larsen, M., Bosen, T., Schonning, K. & Kromann, H. (2005). J. Med. Chem. 48, 2667–2677. Web of Science CrossRef PubMed CAS Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Rizvi, S. U. F., Siddiqui, H. L., Zia-ur-Rehman, M., Azam, M. & Parvez, M. (2010). Acta Cryst. E66, o761. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vaya, J., Belinky, P. A. & Aviram, M. (1997). Free Radic. Biol. Med. 23, 302–313. CrossRef CAS PubMed Web of Science Google Scholar
Wu, J. H., Wang, X. H., Yi, Y. H. & Lee, K. H. (2003). Bioorg. Med. Chem. Lett. 13, 1813–1815. Web of Science CrossRef PubMed CAS Google Scholar
Xia, Y., Yang, Z. Y., Xia, P., Baston, K. F., Nakanishi, Y. & Lee, K. H. (2000). Bioorg. Med. Chem. Lett. 10, 699–701. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 66| Part 4| April 2010| Page o744

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(E)-3-(2-Chloro-6-methyl-3-quinol­yl)-1-(2,3-di­hydro-1,4-benzodioxin-6-yl)prop-2-en-1-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(E)-3-(2-Chloro-6-methyl-3-quinolyl)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)prop-2-en-1-one