7-Chloro-2-[1-(4-methoxy­phen­yl)pyrazol-4-yl]-3,3-dimethyl-3H-indole

Helliwell, M.; Afghan, A.; Keshvari, F.; Baradarani, M.M.; Joule, J.A.

doi:10.1107/S1600536809052581

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o112

doi:10.1107/S1600536809052581

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7-Chloro-2-[1-(4-methoxyphenyl)pyrazol-4-yl]-3,3-dimethyl-3H-indole

Madeleine Helliwell,^a Arash Afghan,^b Foroogh Keshvari,^c Mehdi M. Baradarani ^c ^* and John A. Joule ^a

^aThe School of Chemistry, The University of Manchester, Manchester M13 9PL, England, ^bFaculty of Petroleum Chemistry, Urmia University of Technology, Urmia, Iran, and ^cDepartment of Chemistry, Faculty of Science, University of Urmia, Urmia 57135, Iran
^*Correspondence e-mail: mmbaradarani@yahoo.com

(Received 26 November 2009; accepted 7 December 2009; online 12 December 2009)

In the title compound, C₂₀H₁₈ClN₃O, the dihedral angle between the pyrazole and the 3H-indole components is only 13.28 (6)°, indicating that there is conjugation between the two heterocyclic subunits. The N-methoxyphenyl unit makes a dihedral angle of 25.10 (7)° with the pyrazole ring.

Related literature

For related structures, see: Baradarani et al. (2006 ); Rashidi et al. (2009 ).

Experimental

Crystal data

C₂₀H₁₈ClN₃O
M_r = 351.82
Monoclinic, P 2₁ /n
a = 11.635 (3) Å
b = 10.328 (3) Å
c = 14.141 (4) Å
β = 95.681 (5)°
V = 1690.9 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 100 K
0.50 × 0.40 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
9553 measured reflections
3461 independent reflections
2662 reflections with I > 2σ(I)
R_int = 0.092

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.124
S = 0.97
3461 reflections
229 parameters
H-atom parameters constrained
Δρ_max = 0.70 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2002 ); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809052581/ez2195sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809052581/ez2195Isup2.hkl

checkCIF report

Comment top

We have been studying the interaction of 2,3,3-trimethyl-3H-indoles with the Vilsmeier reagent and discovered that this produced (3,3-dimethyl-2,3-dihydroindol-2-ylidene)malondialdehydes (Baradarani et al., 2006). 2,3,3-trimethyl-3H-pyrrolo[2,3-f]quinoline and 2,3,3-trimethyl-3H-pyrrolo[3,2-h]quinoline behave similarly (Rashidi et al., 2009). The malondialdehydes could be reacted in turn with arylhydrazines to produce mono-arylhydrazones which, on simple reflux in ethanol, were converted into 3,3-dimethyl-2-[1-aryl-1H -pyrazol-4-yl]-3H-indoles (Scheme 2). We now report the crystallographically determined structure of one of these: (1-(4-methoxyphenyl)pyrazol-4-yl)-3H-indole (1).

The structure of (1) reveals the extent of conjugation of the two heterocyclic components of the molecule, i.e. the pyrazole and the 3H-indole. Each of these two components is essential planar; the greatest distance from the least squares plane through the atoms C11 - C13, N2, N3 is 0.004 (2) Å for C11 and the greatest distance from the least squares plane through the atoms C1—C8, N1 is 0.027 (2) Å for C7. Furthermore, the dihedral angle between these two planes is only 13.28 (6) °, indicating conjugation between the two aromatic heterocycles. The N-methoxyphenyl unit, perhaps surprisingly, is not coplanar with its attached pyrazole making a dihedral angle of 25.10 (7) ° with the pyrazole unit.

Related literature top

For related structures, see: Baradarani et al. (2006); Rashidi et al. (2009).

Experimental top

A mixture of 7-chloro-3,3-dimethyl-2,3-dihydroindol- 2-ylidene)malondialdehyde (150 mg, 0.6 mmol) and 4-methoxyphenylhydrazine hydrochloride (110 mg, 0.6 mmol) in ethanol (15 ml) was heated at reflux for 2 h. After this time, the solvent was evaporated and residue recrystallized from absolute ethanol to give 7-chloro-3,3-dimethyl-2- (1-(4-methoxyphenyl)pyrazol-4-yl)-3H-indole (179 mg, 85%). m.p. 464–465 K. ¹H-NMR (CDCl₃) δ 1.56 (6H, s, 2xMe), 3.88 (3H, s, OMe), 7.02 (2H, d, J = 9 Hz, Ar—H), 7.17 (t, J = 7.5 Hz, 1H, H-5), 7.24 (dd, J = 7.5, 1.2 Hz, H-4), 7.35 (1H, dd, J = 7.5, 1.2 Hz, H-6), 7.69 (2H, d, J = 9 Hz, Ar—H), 8.29 (1H, s, pyrazol-5-yl-H), 8.61 (1H, s, pyrazol-3-yl-H). ¹³C-NMR (CDCl₃) δ 24.72, 54.56, 55.61, 114.67, 119.33, 121.15, 126.19, 127.75, 128.32, 140.30, 148.22, 158.91, 179.38. ν_max 3022, 2970, 2927, 1606, 1508, 1255.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. View of the title compound showing the atom numbering scheme with 50% probability displacement ellipsoids.
	Fig. 2. The formation of the title compound.

7-Chloro-2-[1-(4-methoxyphenyl)pyrazol-4-yl]-3,3-dimethyl-3H-indole top

Crystal data top

C₂₀H₁₈ClN₃O	F(000) = 736
M_r = 351.82	D_x = 1.382 Mg m⁻³
Monoclinic, P2₁/n	Melting point = 464–465 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 11.635 (3) Å	Cell parameters from 858 reflections
b = 10.328 (3) Å	θ = 2.9–26.0°
c = 14.141 (4) Å	µ = 0.24 mm⁻¹
β = 95.681 (5)°	T = 100 K
V = 1690.9 (8) Å³	Irregular, yellow
Z = 4	0.50 × 0.40 × 0.20 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2662 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.092
Graphite monochromator	θ_max = 26.4°, θ_min = 2.2°
phi and ω scans	h = −14→14
9553 measured reflections	k = −12→12
3461 independent reflections	l = −10→17

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.0596P)²] where P = (F_o² + 2F_c²)/3
3461 reflections	(Δ/σ)_max = 0.001
229 parameters	Δρ_max = 0.70 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₀H₁₈ClN₃O	V = 1690.9 (8) Å³
M_r = 351.82	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.635 (3) Å	µ = 0.24 mm⁻¹
b = 10.328 (3) Å	T = 100 K
c = 14.141 (4) Å	0.50 × 0.40 × 0.20 mm
β = 95.681 (5)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2662 reflections with I > 2σ(I)
9553 measured reflections	R_int = 0.092
3461 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 0.97	Δρ_max = 0.70 e Å⁻³
3461 reflections	Δρ_min = −0.30 e Å⁻³
229 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	1.22881 (4)	0.17525 (5)	0.17785 (4)	0.02511 (18)
O1	0.48712 (12)	0.88812 (14)	0.58360 (11)	0.0251 (4)
N1	1.03001 (14)	0.27790 (17)	0.29514 (12)	0.0184 (4)
N2	0.81439 (14)	0.57762 (16)	0.43402 (12)	0.0190 (4)
N3	0.91804 (14)	0.62821 (17)	0.41446 (12)	0.0203 (4)
C1	1.04052 (17)	0.1445 (2)	0.27506 (14)	0.0180 (4)
C2	1.12290 (17)	0.0837 (2)	0.22603 (14)	0.0208 (5)
C3	1.11990 (18)	−0.0494 (2)	0.21418 (15)	0.0236 (5)
H3	1.1750	−0.0904	0.1814	0.028*
C4	1.03402 (18)	−0.1217 (2)	0.25156 (15)	0.0249 (5)
H4	1.0329	−0.2112	0.2442	0.030*
C5	0.95010 (19)	−0.0621 (2)	0.29962 (15)	0.0229 (5)
H5	0.8922	−0.1105	0.3237	0.028*
C6	0.95434 (17)	0.0709 (2)	0.31094 (14)	0.0192 (5)
C7	0.87609 (17)	0.16310 (19)	0.35671 (14)	0.0182 (5)
C8	0.93947 (17)	0.2890 (2)	0.34114 (14)	0.0171 (4)
C9	0.86942 (19)	0.1327 (2)	0.46245 (15)	0.0254 (5)
H9A	0.8386	0.0473	0.4688	0.038*
H9B	0.8201	0.1947	0.4890	0.038*
H9C	0.9454	0.1373	0.4957	0.038*
C10	0.75543 (18)	0.1630 (2)	0.30166 (16)	0.0265 (5)
H10A	0.7609	0.1928	0.2380	0.040*
H10B	0.7054	0.2194	0.3327	0.040*
H10C	0.7246	0.0767	0.3000	0.040*
C11	0.90599 (17)	0.41488 (19)	0.37521 (14)	0.0183 (5)
C12	0.80538 (18)	0.4512 (2)	0.41173 (14)	0.0205 (5)
H12	0.7426	0.3980	0.4196	0.025*
C13	0.97206 (17)	0.5295 (2)	0.37985 (14)	0.0196 (5)
H13	1.0460	0.5349	0.3605	0.024*
C14	0.73117 (18)	0.6587 (2)	0.47155 (14)	0.0189 (5)
C15	0.76750 (18)	0.7680 (2)	0.52286 (14)	0.0209 (5)
H15	0.8458	0.7879	0.5318	0.025*
C16	0.68888 (18)	0.8471 (2)	0.56077 (15)	0.0210 (5)
H16	0.7138	0.9209	0.5946	0.025*
C17	0.57208 (18)	0.8165 (2)	0.54834 (15)	0.0202 (5)
C18	0.53577 (18)	0.7079 (2)	0.49591 (15)	0.0223 (5)
H18	0.4575	0.6879	0.4869	0.027*
C19	0.61435 (18)	0.6295 (2)	0.45722 (15)	0.0215 (5)
H19	0.5894	0.5573	0.4216	0.026*
C20	0.5233 (2)	1.0001 (2)	0.63873 (16)	0.0274 (5)
H20A	0.5720	0.9738	0.6942	0.041*
H20B	0.4567	1.0442	0.6577	0.041*
H20C	0.5654	1.0572	0.6012	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0224 (3)	0.0279 (3)	0.0255 (3)	0.0004 (2)	0.0048 (2)	0.0008 (2)
O1	0.0289 (8)	0.0239 (8)	0.0229 (9)	0.0037 (7)	0.0038 (7)	−0.0050 (7)
N1	0.0208 (9)	0.0183 (9)	0.0151 (9)	0.0010 (7)	−0.0019 (7)	0.0004 (7)
N2	0.0212 (9)	0.0192 (9)	0.0161 (9)	−0.0004 (7)	−0.0009 (7)	0.0000 (7)
N3	0.0212 (9)	0.0220 (9)	0.0174 (9)	−0.0015 (8)	0.0007 (8)	0.0005 (7)
C1	0.0186 (10)	0.0201 (11)	0.0142 (11)	0.0020 (8)	−0.0041 (9)	0.0015 (8)
C2	0.0188 (10)	0.0269 (12)	0.0161 (11)	−0.0005 (9)	−0.0014 (9)	0.0028 (9)
C3	0.0260 (11)	0.0249 (12)	0.0193 (12)	0.0062 (10)	−0.0011 (9)	−0.0027 (9)
C4	0.0281 (12)	0.0207 (11)	0.0249 (13)	0.0018 (10)	−0.0031 (10)	−0.0016 (9)
C5	0.0244 (11)	0.0234 (12)	0.0204 (12)	−0.0033 (9)	−0.0003 (9)	−0.0007 (9)
C6	0.0221 (10)	0.0214 (11)	0.0128 (11)	0.0003 (9)	−0.0038 (8)	0.0014 (8)
C7	0.0203 (10)	0.0193 (11)	0.0147 (11)	0.0002 (8)	0.0008 (9)	0.0001 (8)
C8	0.0195 (10)	0.0204 (11)	0.0103 (10)	0.0015 (8)	−0.0046 (8)	0.0017 (8)
C9	0.0333 (12)	0.0233 (11)	0.0203 (12)	0.0002 (10)	0.0059 (10)	0.0018 (9)
C10	0.0231 (11)	0.0272 (12)	0.0287 (13)	0.0003 (10)	−0.0002 (10)	−0.0067 (10)
C11	0.0215 (10)	0.0200 (11)	0.0127 (10)	0.0017 (9)	−0.0017 (8)	0.0038 (8)
C12	0.0244 (11)	0.0178 (11)	0.0188 (11)	−0.0020 (9)	−0.0009 (9)	0.0013 (8)
C13	0.0190 (10)	0.0234 (11)	0.0160 (11)	0.0028 (9)	−0.0002 (9)	0.0021 (9)
C14	0.0232 (11)	0.0202 (11)	0.0127 (11)	0.0035 (9)	−0.0007 (9)	0.0017 (8)
C15	0.0222 (10)	0.0231 (11)	0.0162 (11)	−0.0006 (9)	−0.0035 (9)	0.0027 (9)
C16	0.0275 (11)	0.0183 (11)	0.0163 (11)	−0.0019 (9)	−0.0020 (9)	−0.0008 (9)
C17	0.0269 (11)	0.0200 (11)	0.0133 (11)	0.0025 (9)	0.0008 (9)	0.0023 (8)
C18	0.0207 (10)	0.0249 (12)	0.0206 (12)	−0.0013 (9)	−0.0010 (9)	0.0005 (9)
C19	0.0274 (11)	0.0182 (11)	0.0179 (11)	−0.0022 (9)	−0.0020 (9)	−0.0023 (9)
C20	0.0393 (14)	0.0223 (12)	0.0206 (12)	0.0051 (10)	0.0030 (10)	−0.0042 (9)

Geometric parameters (Å, º) top

Cl1—C2	1.744 (2)	C9—H9A	0.9600
O1—C17	1.367 (2)	C9—H9B	0.9600
O1—C20	1.434 (2)	C9—H9C	0.9600
N1—C8	1.297 (2)	C10—H10A	0.9600
N1—C1	1.415 (3)	C10—H10B	0.9600
N2—C12	1.344 (3)	C10—H10C	0.9600
N2—N3	1.367 (2)	C11—C12	1.378 (3)
N2—C14	1.422 (3)	C11—C13	1.410 (3)
N3—C13	1.317 (3)	C12—H12	0.9300
C1—C2	1.387 (3)	C13—H13	0.9300
C1—C6	1.393 (3)	C14—C15	1.384 (3)
C2—C3	1.385 (3)	C14—C19	1.387 (3)
C3—C4	1.393 (3)	C15—C16	1.375 (3)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.388 (3)	C16—C17	1.389 (3)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.383 (3)	C17—C18	1.388 (3)
C5—H5	0.9300	C18—C19	1.375 (3)
C6—C7	1.507 (3)	C18—H18	0.9300
C7—C8	1.521 (3)	C19—H19	0.9300
C7—C10	1.536 (3)	C20—H20A	0.9600
C7—C9	1.537 (3)	C20—H20B	0.9600
C8—C11	1.453 (3)	C20—H20C	0.9600

C17—O1—C20	116.76 (16)	C7—C10—H10A	109.5
C8—N1—C1	106.09 (17)	C7—C10—H10B	109.5
C12—N2—N3	111.93 (16)	H10A—C10—H10B	109.5
C12—N2—C14	128.26 (17)	C7—C10—H10C	109.5
N3—N2—C14	119.80 (16)	H10A—C10—H10C	109.5
C13—N3—N2	104.03 (16)	H10B—C10—H10C	109.5
C2—C1—C6	119.53 (19)	C12—C11—C13	103.48 (18)
C2—C1—N1	128.23 (18)	C12—C11—C8	129.33 (19)
C6—C1—N1	112.24 (17)	C13—C11—C8	127.18 (18)
C3—C2—C1	119.95 (19)	N2—C12—C11	107.65 (18)
C3—C2—Cl1	120.07 (16)	N2—C12—H12	126.2
C1—C2—Cl1	119.97 (17)	C11—C12—H12	126.2
C2—C3—C4	119.77 (19)	N3—C13—C11	112.91 (18)
C2—C3—H3	120.1	N3—C13—H13	123.5
C4—C3—H3	120.1	C11—C13—H13	123.5
C5—C4—C3	120.9 (2)	C15—C14—C19	119.85 (19)
C5—C4—H4	119.5	C15—C14—N2	119.45 (18)
C3—C4—H4	119.5	C19—C14—N2	120.70 (18)
C6—C5—C4	118.58 (19)	C16—C15—C14	120.6 (2)
C6—C5—H5	120.7	C16—C15—H15	119.7
C4—C5—H5	120.7	C14—C15—H15	119.7
C5—C6—C1	121.21 (19)	C15—C16—C17	119.71 (19)
C5—C6—C7	131.37 (19)	C15—C16—H16	120.1
C1—C6—C7	107.40 (17)	C17—C16—H16	120.1
C6—C7—C8	98.95 (16)	O1—C17—C18	116.06 (18)
C6—C7—C10	110.03 (17)	O1—C17—C16	124.34 (19)
C8—C7—C10	111.04 (17)	C18—C17—C16	119.59 (19)
C6—C7—C9	112.32 (17)	C19—C18—C17	120.63 (19)
C8—C7—C9	112.76 (17)	C19—C18—H18	119.7
C10—C7—C9	111.17 (17)	C17—C18—H18	119.7
N1—C8—C11	120.19 (19)	C18—C19—C14	119.63 (19)
N1—C8—C7	115.26 (18)	C18—C19—H19	120.2
C11—C8—C7	124.54 (18)	C14—C19—H19	120.2
C7—C9—H9A	109.5	O1—C20—H20A	109.5
C7—C9—H9B	109.5	O1—C20—H20B	109.5
H9A—C9—H9B	109.5	H20A—C20—H20B	109.5
C7—C9—H9C	109.5	O1—C20—H20C	109.5
H9A—C9—H9C	109.5	H20A—C20—H20C	109.5
H9B—C9—H9C	109.5	H20B—C20—H20C	109.5

C12—N2—N3—C13	−0.1 (2)	C10—C7—C8—C11	67.3 (2)
C14—N2—N3—C13	−178.87 (18)	C9—C7—C8—C11	−58.2 (3)
C8—N1—C1—C2	179.1 (2)	N1—C8—C11—C12	168.9 (2)
C8—N1—C1—C6	−0.8 (2)	C7—C8—C11—C12	−12.2 (3)
C6—C1—C2—C3	−0.8 (3)	N1—C8—C11—C13	−12.4 (3)
N1—C1—C2—C3	179.3 (2)	C7—C8—C11—C13	166.5 (2)
C6—C1—C2—Cl1	178.18 (15)	N3—N2—C12—C11	−0.4 (2)
N1—C1—C2—Cl1	−1.6 (3)	C14—N2—C12—C11	178.24 (19)
C1—C2—C3—C4	0.0 (3)	C13—C11—C12—N2	0.7 (2)
Cl1—C2—C3—C4	−179.00 (16)	C8—C11—C12—N2	179.67 (19)
C2—C3—C4—C5	0.9 (3)	N2—N3—C13—C11	0.6 (2)
C3—C4—C5—C6	−0.9 (3)	C12—C11—C13—N3	−0.8 (2)
C4—C5—C6—C1	0.1 (3)	C8—C11—C13—N3	−179.82 (19)
C4—C5—C6—C7	178.4 (2)	C12—N2—C14—C15	155.5 (2)
C2—C1—C6—C5	0.8 (3)	N3—N2—C14—C15	−26.0 (3)
N1—C1—C6—C5	−179.35 (19)	C12—N2—C14—C19	−24.5 (3)
C2—C1—C6—C7	−177.89 (18)	N3—N2—C14—C19	154.00 (19)
N1—C1—C6—C7	2.0 (2)	C19—C14—C15—C16	0.8 (3)
C5—C6—C7—C8	179.4 (2)	N2—C14—C15—C16	−179.27 (18)
C1—C6—C7—C8	−2.1 (2)	C14—C15—C16—C17	0.7 (3)
C5—C6—C7—C10	−64.3 (3)	C20—O1—C17—C18	179.43 (18)
C1—C6—C7—C10	114.23 (19)	C20—O1—C17—C16	−1.5 (3)
C5—C6—C7—C9	60.1 (3)	C15—C16—C17—O1	179.54 (19)
C1—C6—C7—C9	−121.36 (19)	C15—C16—C17—C18	−1.5 (3)
C1—N1—C8—C11	178.18 (17)	O1—C17—C18—C19	179.89 (18)
C1—N1—C8—C7	−0.8 (2)	C16—C17—C18—C19	0.8 (3)
C6—C7—C8—N1	1.9 (2)	C17—C18—C19—C14	0.6 (3)
C10—C7—C8—N1	−113.7 (2)	C15—C14—C19—C18	−1.4 (3)
C9—C7—C8—N1	120.8 (2)	N2—C14—C19—C18	178.62 (19)
C6—C7—C8—C11	−177.07 (18)

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈ClN₃O
M_r	351.82
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	11.635 (3), 10.328 (3), 14.141 (4)
β (°)	95.681 (5)
V (Å³)	1690.9 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.50 × 0.40 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9553, 3461, 2662
R_int	0.092
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.124, 0.97
No. of reflections	3461
No. of parameters	229
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.70, −0.30

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors are grateful to the University of Urmia for financial support of the preparative aspects of this work.

References

Baradarani, M. M., Afghan, A., Zebarjadi, F., Hasanzadeh, K. & Joule, J. A. (2006). J. Heterocycl. Chem. 43, 1591–1596. CrossRef CAS Google Scholar
Bruker (2001). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2002). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Rashidi, A., Afghan, A., Baradarani, M. M. & Joule, J. A. (2009). J. Heterocycl. Chem. 46, 428–431. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar