(Z)-N-[5-Bromo-2-(4-methyl­anilino)-3H-indol-3-yl­idene]-4-methyl­aniline oxide

Asgri, D.; Ghanbari, M.; Mehrdad, M.; Jadidi, K.; Khavasi, H.R.

doi:10.1107/S1600536811000833

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o350

doi:10.1107/S1600536811000833

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(Z)-N-[5-Bromo-2-(4-methylanilino)-3H-indol-3-ylidene]-4-methylaniline oxide

Davood Asgri,^a Mohammad Ghanbari,^a Morteza Mehrdad,^b ^* Khosrow Jadidi ^a and Hamid Reza Khavasi ^a

^aDepartement of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran, and ^bDepartment of Environmental Pollution, Environmental Sciences Research Institute, Shahid Beheshti University, G.C., Evin, Tehran 1983963113, Iran
^*Correspondence e-mail: m_mehrdad4@yahoo.com

(Received 5 January 2011; accepted 6 January 2011; online 12 January 2011)

The crystal structure of the title compound, C₂₂H₁₈BrN₃O, is stabilized by π–π contacts [centroid–centroid distance = 3.476 (2) Å] between five-membered rings as well as intermolecular C—H⋯O and C—H⋯N hydrogen bonds. An intramolecular N—H⋯O hydrogen bond occurs. The benzene rings make a dihedral angle of 59.89 (8)°. The dihedral angles between the fused ring systemand the two benzene rings are 3.46 (7) and 61.97 (7)°.

Related literature

For background to this study and a related structure, see: Mehrdad et al. (2011 ). For the Baeyer–Villiger oxidation of 1-alkyl-3-arylimino-2-indolinones, see: Jadidi et al. (2008 ); Azizian et al. (2010 ).

Experimental

Crystal data

C₂₂H₁₈BrN₃O
M_r = 420.29
Triclinic, $[P \overline 1]$
a = 7.8676 (4) Å
b = 8.9748 (4) Å
c = 14.1353 (7) Å
α = 83.090 (4)°
β = 74.363 (4)°
γ = 69.776 (4)°
V = 901.49 (8) Å³
Z = 2
Mo Kα radiation
μ = 2.30 mm⁻¹
T = 298 K
0.3 × 0.16 × 0.11 mm

Data collection

Stoe IPDS IIT diffractometer
Absorption correction: numerical [shape of crystal determined optically (X-RED and X-SHAPE; Stoe & Cie, 2005 ) T_min = 0.681, T_max = 0.805
9841 measured reflections
4839 independent reflections
4382 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.119
S = 1.10
4839 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.91 e Å⁻³
Δρ_min = −1.10 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O1	0.86	1.99	2.677 (3)	137
C16—H16⋯N3ⁱ	0.93	2.45	3.369 (3)	169
C20—H20⋯O1ⁱⁱ	0.93	2.62	3.434 (3)	146
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) x-1, y+1, z.

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-AREA; 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: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811000833/bt5458sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811000833/bt5458Isup2.hkl

checkCIF report

Comment top

The background to this study is set out in the preceding paper (Mehrdad et al., 2011). In this paper, we report the structure of N-aryl-N-(2-arylamino-3H-indol-3-ylidene) amine N-oxide. The molecular structure of the title compound is shown in Fig. 1.

In the molecules of the title compound, bond distances and angles are within normal ranges.

The dihedral angles between the rings are A (C1—C7), B (C10—C16) and C (C17—C22/N3/C8/C9) are A/B = 59.89 (8)°, A/C = 3.46 (7)° and B/C = 61.97 (7)°. A packing diagram is shown in Fig. 2. Intermolecular C—H···N contacts and π–π interactions between 5-membered rings [centroid···centroid distance = 3.476 (2) Å; symmetry operator 2-x,2-y,1-z] stabilize the crystal structure.

Related literature top

For background to this study and a related structure, see: Mehrdad et al. (2011). For the Baeyer–Villiger oxidation of 1-alkyl-3-arylimino-2-indolinones, see: Jadidi et al. (2008); Azizian et al. (2010).

Experimental top

The preparation of the title compound has been reported previously, except that the temperature was room temperature in place of -20°C (Mehrdad et al., 2010). At -20°C (2Z)-N-(4-Methoxyphenyl)-2-(4-methoxyphenylimino)-2H-1,4-benzoxazin-3-amine was obtained, whereas at room temperature (Z)—N-(5-bromo-2-(p-tolylamino)-3H-indol-3- ylidene)-4-methylaniline oxide was obtained. It was isolated as a violet solid in 72% yield: m.p. = 183–184 C.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); 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: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

(Z)-N-[5-Bromo-2-(4-methylanilino)-3H-indol-3- ylidene]-4-methylaniline oxide top

Crystal data top

C₂₂H₁₈BrN₃O	Z = 2
M_r = 420.29	F(000) = 428
Triclinic, P1	D_x = 1.548 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8676 (4) Å	Cell parameters from 9841 reflections
b = 8.9748 (4) Å	θ = 2.4–29.1°
c = 14.1353 (7) Å	µ = 2.30 mm⁻¹
α = 83.090 (4)°	T = 298 K
β = 74.363 (4)°	Prism, red
γ = 69.776 (4)°	0.3 × 0.16 × 0.11 mm
V = 901.49 (8) Å³

Data collection top

Stoe IPDS IIT diffractometer	4839 independent reflections
Graphite monochromator	4382 reflections with I > 2σ(I)
Detector resolution: 0.15 mm pixels mm^-1	R_int = 0.049
rotation method scans	θ_max = 29.1°, θ_min = 2.4°
Absorption correction: numerical [shape of crystal determined optically (X-RED and X-SHAPE; Stoe & Cie, 2005)	h = −10→10
T_min = 0.681, T_max = 0.805	k = −12→12
9841 measured reflections	l = −19→14

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0603P)² + 1.2665P] where P = (F_o² + 2F_c²)/3
4839 reflections	(Δ/σ)_max = 0.008
244 parameters	Δρ_max = 0.91 e Å⁻³
0 restraints	Δρ_min = −1.10 e Å⁻³

Crystal data top

C₂₂H₁₈BrN₃O	γ = 69.776 (4)°
M_r = 420.29	V = 901.49 (8) Å³
Triclinic, P1	Z = 2
a = 7.8676 (4) Å	Mo Kα radiation
b = 8.9748 (4) Å	µ = 2.30 mm⁻¹
c = 14.1353 (7) Å	T = 298 K
α = 83.090 (4)°	0.3 × 0.16 × 0.11 mm
β = 74.363 (4)°

Data collection top

Stoe IPDS IIT diffractometer	4839 independent reflections
Absorption correction: numerical [shape of crystal determined optically (X-RED and X-SHAPE; Stoe & Cie, 2005)	4382 reflections with I > 2σ(I)
T_min = 0.681, T_max = 0.805	R_int = 0.049
9841 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.10	Δρ_max = 0.91 e Å⁻³
4839 reflections	Δρ_min = −1.10 e Å⁻³
244 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	1.0280 (4)	0.6363 (3)	0.3135 (2)	0.0203 (5)
H1	0.9265	0.7273	0.3328	0.024*
C2	1.0624 (4)	0.5714 (3)	0.2226 (2)	0.0219 (5)
H2	0.9835	0.6211	0.1814	0.026*
C3	1.2118 (4)	0.4339 (3)	0.1920 (2)	0.0208 (5)
C4	1.2539 (4)	0.3684 (4)	0.0918 (2)	0.0288 (6)
H4A	1.2522	0.2611	0.099	0.035*
H4B	1.3751	0.3699	0.0548	0.035*
H4C	1.1613	0.4324	0.0581	0.035*
C5	1.3260 (4)	0.3607 (3)	0.2564 (2)	0.0219 (5)
H5	1.4245	0.2673	0.2384	0.026*
C6	1.2958 (4)	0.4239 (3)	0.3460 (2)	0.0199 (5)
H6	1.3745	0.3736	0.3873	0.024*
C7	1.1468 (3)	0.5638 (3)	0.37508 (19)	0.0173 (4)
C8	0.9991 (3)	0.7513 (3)	0.51299 (19)	0.0162 (4)
C9	1.0160 (3)	0.7961 (3)	0.60744 (19)	0.0167 (4)
C10	1.1776 (3)	0.7865 (3)	0.73329 (19)	0.0169 (4)
C11	1.1803 (4)	0.6950 (3)	0.8196 (2)	0.0196 (5)
H11	1.1661	0.5956	0.8241	0.023*
C12	1.2048 (4)	0.7557 (3)	0.8991 (2)	0.0206 (5)
H12	1.2046	0.6967	0.9579	0.025*
C13	1.2295 (4)	0.9033 (3)	0.89224 (19)	0.0195 (5)
C14	1.2576 (4)	0.9686 (4)	0.9787 (2)	0.0268 (6)
H14A	1.1625	1.0694	0.9953	0.032*
H14B	1.3783	0.9819	0.9616	0.032*
H14C	1.2499	0.8959	1.0341	0.032*
C15	1.2301 (4)	0.9902 (3)	0.8033 (2)	0.0194 (5)
H15	1.2478	1.0884	0.7977	0.023*
C16	1.2046 (4)	0.9327 (3)	0.7233 (2)	0.0192 (5)
H16	1.2056	0.991	0.6642	0.023*
C17	0.8539 (3)	0.9366 (3)	0.63666 (19)	0.0159 (4)
C18	0.7762 (3)	1.0326 (3)	0.71857 (18)	0.0174 (5)
H18	0.8311	1.0128	0.7714	0.021*
C19	0.6130 (3)	1.1593 (3)	0.71750 (19)	0.0171 (4)
C20	0.5291 (4)	1.1944 (3)	0.6390 (2)	0.0190 (5)
H20	0.4235	1.2832	0.64	0.023*
C21	0.6048 (4)	1.0953 (3)	0.55863 (19)	0.0189 (5)
H21	0.5489	1.1161	0.5061	0.023*
C22	0.7650 (3)	0.9650 (3)	0.55820 (18)	0.0166 (4)
N1	1.1289 (3)	0.6222 (3)	0.46644 (16)	0.0177 (4)
H1B	1.2127	0.568	0.497	0.021*
N2	1.1553 (3)	0.7223 (2)	0.64904 (17)	0.0176 (4)
N3	0.8540 (3)	0.8514 (2)	0.48464 (16)	0.0166 (4)
O1	1.2865 (3)	0.5915 (2)	0.61671 (15)	0.0233 (4)
Br1	0.49974 (4)	1.28997 (3)	0.82884 (2)	0.02254 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0190 (11)	0.0149 (11)	0.0265 (13)	−0.0007 (9)	−0.0084 (10)	−0.0072 (9)
C2	0.0230 (12)	0.0170 (11)	0.0264 (13)	−0.0033 (10)	−0.0090 (10)	−0.0068 (10)
C3	0.0185 (11)	0.0188 (11)	0.0251 (12)	−0.0055 (9)	−0.0030 (10)	−0.0084 (10)
C4	0.0300 (14)	0.0300 (14)	0.0257 (13)	−0.0073 (12)	−0.0032 (11)	−0.0138 (11)
C5	0.0164 (11)	0.0164 (11)	0.0292 (13)	−0.0019 (9)	−0.0014 (10)	−0.0072 (10)
C6	0.0166 (11)	0.0148 (11)	0.0255 (12)	−0.0013 (9)	−0.0046 (9)	−0.0033 (9)
C7	0.0163 (10)	0.0136 (10)	0.0218 (11)	−0.0038 (9)	−0.0036 (9)	−0.0052 (9)
C8	0.0172 (11)	0.0115 (10)	0.0200 (11)	−0.0044 (8)	−0.0041 (9)	−0.0034 (8)
C9	0.0162 (11)	0.0125 (10)	0.0211 (11)	−0.0024 (8)	−0.0063 (9)	−0.0019 (8)
C10	0.0149 (10)	0.0142 (10)	0.0208 (11)	−0.0005 (8)	−0.0075 (9)	−0.0037 (8)
C11	0.0207 (11)	0.0134 (10)	0.0250 (12)	−0.0042 (9)	−0.0083 (10)	−0.0003 (9)
C12	0.0210 (12)	0.0208 (12)	0.0193 (11)	−0.0039 (10)	−0.0078 (9)	−0.0002 (9)
C13	0.0158 (11)	0.0198 (11)	0.0205 (12)	−0.0009 (9)	−0.0041 (9)	−0.0077 (9)
C14	0.0275 (14)	0.0301 (14)	0.0241 (13)	−0.0058 (11)	−0.0096 (11)	−0.0094 (11)
C15	0.0189 (11)	0.0134 (10)	0.0252 (12)	−0.0028 (9)	−0.0064 (10)	−0.0033 (9)
C16	0.0205 (11)	0.0141 (10)	0.0215 (12)	−0.0026 (9)	−0.0065 (9)	−0.0016 (9)
C17	0.0148 (10)	0.0127 (10)	0.0205 (11)	−0.0034 (8)	−0.0054 (9)	−0.0026 (8)
C18	0.0182 (11)	0.0156 (11)	0.0178 (11)	−0.0035 (9)	−0.0053 (9)	−0.0033 (8)
C19	0.0154 (10)	0.0131 (10)	0.0207 (11)	−0.0022 (8)	−0.0013 (9)	−0.0069 (8)
C20	0.0175 (11)	0.0146 (10)	0.0241 (12)	−0.0022 (9)	−0.0071 (9)	−0.0020 (9)
C21	0.0191 (11)	0.0160 (11)	0.0215 (12)	−0.0038 (9)	−0.0075 (9)	−0.0008 (9)
C22	0.0178 (11)	0.0146 (10)	0.0184 (11)	−0.0058 (9)	−0.0051 (9)	−0.0016 (8)
N1	0.0170 (9)	0.0148 (9)	0.0209 (10)	−0.0016 (8)	−0.0069 (8)	−0.0040 (8)
N2	0.0165 (9)	0.0119 (9)	0.0234 (10)	−0.0010 (7)	−0.0070 (8)	−0.0027 (8)
N3	0.0175 (9)	0.0137 (9)	0.0180 (9)	−0.0031 (8)	−0.0048 (8)	−0.0035 (7)
O1	0.0207 (9)	0.0149 (8)	0.0308 (10)	0.0043 (7)	−0.0107 (8)	−0.0089 (7)
Br1	0.02190 (14)	0.01708 (13)	0.02465 (15)	−0.00021 (9)	−0.00401 (10)	−0.00834 (9)

Geometric parameters (Å, º) top

C1—C7	1.391 (4)	C11—H11	0.93
C1—C2	1.396 (4)	C12—C13	1.393 (4)
C1—H1	0.93	C12—H12	0.93
C2—C3	1.394 (4)	C13—C15	1.397 (4)
C2—H2	0.93	C13—C14	1.515 (4)
C3—C5	1.398 (4)	C14—H14A	0.96
C3—C4	1.507 (4)	C14—H14B	0.96
C4—H4A	0.96	C14—H14C	0.96
C4—H4B	0.96	C15—C16	1.385 (4)
C4—H4C	0.96	C15—H15	0.93
C5—C6	1.378 (4)	C16—H16	0.93
C5—H5	0.93	C17—C18	1.397 (3)
C6—C7	1.403 (3)	C17—C22	1.418 (3)
C6—H6	0.93	C18—C19	1.393 (3)
C7—N1	1.406 (3)	C18—H18	0.93
C8—N3	1.312 (3)	C19—C20	1.391 (4)
C8—N1	1.349 (3)	C19—Br1	1.901 (2)
C8—C9	1.491 (3)	C20—C21	1.395 (4)
C9—N2	1.318 (3)	C20—H20	0.93
C9—C17	1.455 (3)	C21—C22	1.391 (3)
C10—C16	1.385 (4)	C21—H21	0.93
C10—C11	1.387 (4)	C22—N3	1.407 (3)
C10—N2	1.459 (3)	N1—H1B	0.86
C11—C12	1.390 (4)	N2—O1	1.300 (3)

C7—C1—C2	119.5 (2)	C12—C13—C14	121.1 (3)
C7—C1—H1	120.2	C15—C13—C14	120.3 (2)
C2—C1—H1	120.2	C13—C14—H14A	109.5
C3—C2—C1	121.7 (3)	C13—C14—H14B	109.5
C3—C2—H2	119.1	H14A—C14—H14B	109.5
C1—C2—H2	119.1	C13—C14—H14C	109.5
C2—C3—C5	117.7 (2)	H14A—C14—H14C	109.5
C2—C3—C4	121.6 (3)	H14B—C14—H14C	109.5
C5—C3—C4	120.7 (2)	C16—C15—C13	121.2 (2)
C3—C4—H4A	109.5	C16—C15—H15	119.4
C3—C4—H4B	109.5	C13—C15—H15	119.4
H4A—C4—H4B	109.5	C15—C16—C10	118.5 (2)
C3—C4—H4C	109.5	C15—C16—H16	120.8
H4A—C4—H4C	109.5	C10—C16—H16	120.8
H4B—C4—H4C	109.5	C18—C17—C22	120.8 (2)
C6—C5—C3	121.5 (2)	C18—C17—C9	135.5 (2)
C6—C5—H5	119.2	C22—C17—C9	103.6 (2)
C3—C5—H5	119.2	C19—C18—C17	117.0 (2)
C5—C6—C7	120.1 (2)	C19—C18—H18	121.5
C5—C6—H6	119.9	C17—C18—H18	121.5
C7—C6—H6	119.9	C20—C19—C18	123.1 (2)
C1—C7—C6	119.4 (2)	C20—C19—Br1	118.58 (18)
C1—C7—N1	124.2 (2)	C18—C19—Br1	118.31 (19)
C6—C7—N1	116.4 (2)	C19—C20—C21	119.5 (2)
N3—C8—N1	128.1 (2)	C19—C20—H20	120.3
N3—C8—C9	112.3 (2)	C21—C20—H20	120.3
N1—C8—C9	119.6 (2)	C22—C21—C20	119.1 (2)
N2—C9—C17	130.5 (2)	C22—C21—H21	120.5
N2—C9—C8	124.9 (2)	C20—C21—H21	120.5
C17—C9—C8	104.6 (2)	C21—C22—N3	125.9 (2)
C16—C10—C11	122.1 (2)	C21—C22—C17	120.4 (2)
C16—C10—N2	119.2 (2)	N3—C22—C17	113.7 (2)
C11—C10—N2	118.6 (2)	C8—N1—C7	129.2 (2)
C10—C11—C12	118.4 (2)	C8—N1—H1B	115.4
C10—C11—H11	120.8	C7—N1—H1B	115.4
C12—C11—H11	120.8	O1—N2—C9	123.3 (2)
C11—C12—C13	121.2 (2)	O1—N2—C10	114.8 (2)
C11—C12—H12	119.4	C9—N2—C10	121.8 (2)
C13—C12—H12	119.4	C8—N3—C22	105.6 (2)
C12—C13—C15	118.7 (2)

C7—C1—C2—C3	0.9 (4)	C9—C17—C18—C19	−179.4 (3)
C1—C2—C3—C5	1.0 (4)	C17—C18—C19—C20	−1.3 (4)
C1—C2—C3—C4	−177.1 (3)	C17—C18—C19—Br1	178.59 (18)
C2—C3—C5—C6	−1.7 (4)	C18—C19—C20—C21	3.1 (4)
C4—C3—C5—C6	176.3 (3)	Br1—C19—C20—C21	−176.81 (19)
C3—C5—C6—C7	0.7 (4)	C19—C20—C21—C22	−1.3 (4)
C2—C1—C7—C6	−1.9 (4)	C20—C21—C22—N3	177.6 (2)
C2—C1—C7—N1	177.7 (3)	C20—C21—C22—C17	−2.2 (4)
C5—C6—C7—C1	1.2 (4)	C18—C17—C22—C21	4.0 (4)
C5—C6—C7—N1	−178.5 (2)	C9—C17—C22—C21	−178.0 (2)
N3—C8—C9—N2	−175.3 (2)	C18—C17—C22—N3	−175.8 (2)
N1—C8—C9—N2	3.0 (4)	C9—C17—C22—N3	2.2 (3)
N3—C8—C9—C17	2.5 (3)	N3—C8—N1—C7	2.1 (4)
N1—C8—C9—C17	−179.2 (2)	C9—C8—N1—C7	−175.9 (2)
C16—C10—C11—C12	2.2 (4)	C1—C7—N1—C8	1.4 (4)
N2—C10—C11—C12	179.0 (2)	C6—C7—N1—C8	−178.9 (3)
C10—C11—C12—C13	−1.2 (4)	C17—C9—N2—O1	176.1 (2)
C11—C12—C13—C15	−0.2 (4)	C8—C9—N2—O1	−6.7 (4)
C11—C12—C13—C14	−179.5 (2)	C17—C9—N2—C10	−6.7 (4)
C12—C13—C15—C16	0.7 (4)	C8—C9—N2—C10	170.5 (2)
C14—C13—C15—C16	180.0 (2)	C16—C10—N2—O1	115.9 (3)
C13—C15—C16—C10	0.3 (4)	C11—C10—N2—O1	−60.9 (3)
C11—C10—C16—C15	−1.7 (4)	C16—C10—N2—C9	−61.5 (3)
N2—C10—C16—C15	−178.5 (2)	C11—C10—N2—C9	121.7 (3)
N2—C9—C17—C18	−7.4 (5)	N1—C8—N3—C22	−179.3 (3)
C8—C9—C17—C18	175.0 (3)	C9—C8—N3—C22	−1.2 (3)
N2—C9—C17—C22	175.1 (3)	C21—C22—N3—C8	179.5 (3)
C8—C9—C17—C22	−2.6 (3)	C17—C22—N3—C8	−0.6 (3)
C22—C17—C18—C19	−2.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O1	0.86	1.99	2.677 (3)	137
C16—H16···N3ⁱ	0.93	2.45	3.369 (3)	169
C20—H20···O1ⁱⁱ	0.93	2.62	3.434 (3)	146

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

Experimental details

Crystal data
Chemical formula	C₂₂H₁₈BrN₃O
M_r	420.29
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.8676 (4), 8.9748 (4), 14.1353 (7)
α, β, γ (°)	83.090 (4), 74.363 (4), 69.776 (4)
V (Å³)	901.49 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.30
Crystal size (mm)	0.3 × 0.16 × 0.11

Data collection
Diffractometer	Stoe IPDS IIT diffractometer
Absorption correction	Numerical [shape of crystal determined optically (X-RED and X-SHAPE; Stoe & Cie, 2005)
T_min, T_max	0.681, 0.805
No. of measured, independent and observed [I > 2σ(I)] reflections	9841, 4839, 4382
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.685

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.119, 1.10
No. of reflections	4839
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.91, −1.10

Computer programs: X-AREA (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O1	0.86	1.99	2.677 (3)	137
C16—H16···N3ⁱ	0.93	2.45	3.369 (3)	169
C20—H20···O1ⁱⁱ	0.93	2.615	3.434 (3)	146

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

Acknowledgements

The authors thank the Vice President of Research Affairs at Shahid Beheshti University, General Campus, for financial support.

References

Azizian, J., Mehrdad, M., Jadidi, K. & Sarrafi, Y. (2010). Tetrahedron Lett. 41, 5265–5268. Web of Science CrossRef Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Jadidi, K., Ghahremanzadeh, R., Mehrdad, M., Ghanbari, M. & Arvin-Nezhad, H. (2008). Monatsh. Chem. 139, 277–280. Web of Science CSD CrossRef CAS Google Scholar
Mehrdad, M., Ghanbari, M., Jadidi, K., Salemi, A. & Khavasi, H. R. (2011). Acta Cryst. E67, o49. 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
Stoe & Cie (2005). X-AREA, X-RED and X-SHAPE. Stoe & Cie, Darmstadt, Germany. Google Scholar

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Volume 67| Part 2| February 2011| Page o350

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

(Z)-N-[5-Bromo-2-(4-methyl­anilino)-3H-indol-3-yl­­idene]-4-methyl­aniline oxide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(Z)-N-[5-Bromo-2-(4-methylanilino)-3H-indol-3-ylidene]-4-methylaniline oxide