N′-[(E)-4-Meth­oxy­benzyl­idene]-2-(5-meth­oxy-2-methyl-1H-indol-3-yl)acetohydrazide

Akkurt, M.; Mague, J.T.; Mohamed, S.K.; Abelhamid, A.A.; Albayati, M.R.

doi:10.1107/S1600536813027050

organic compounds

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ISSN: 2056-9890

Volume 69| Part 11| November 2013| Pages o1660-o1661

doi:10.1107/S1600536813027050

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N′-[(E)-4-Methoxybenzylidene]-2-(5-methoxy-2-methyl-1H-indol-3-yl)acetohydrazide

Mehmet Akkurt,^a Joel T. Mague,^b Shaaban K. Mohamed,^c,^d Antar A. Abelhamid ^e and Mustafa R. Albayati ^f ^*

^aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^cChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^dChemistry Department, Faculty of Science, Mini University, 61519 El-Minia, Egypt, ^eDepartment of Chemistry, Faculty of Science, Sohag University, 82524 Sohag, Egypt, and ^fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

(Received 30 September 2013; accepted 2 October 2013; online 19 October 2013)

The conformation adopted by the title compound, C₂₀H₂₁N₃O₃, in the crystal is `J'-shaped and appears to be at least partially directed by a weak intramolecular C—H⋯N hydrogen bond. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, forming dimers with R₂²(8) motifs. Furthermore, these dimers connect to each other via C—H⋯O and N—H⋯O hydrogen bonds to form a three-dimensional network.

CCDC reference: 964356

Related literature

For general medical applications of non-steriodal anti-inflammatory drugs (NSAIDs), see: Richy et al. (2004 ). For the undesirable side effects of such drugs, see: Allison et al. (1992 ); McMahon (2001 ); Rocha et al. (2001 ); Halen et al. (2009 ). For a similar structure, see: Mague et al. (2013 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₀H₂₁N₃O₃
M_r = 351.40
Triclinic, $[P \overline 1]$
a = 7.1894 (2) Å
b = 10.4055 (3) Å
c = 12.4403 (4) Å
α = 107.983 (2)°
β = 92.451 (2)°
γ = 97.882 (2)°
V = 873.24 (5) Å³
Z = 2
Cu Kα radiation
μ = 0.74 mm⁻¹
T = 100 K
0.14 × 0.12 × 0.08 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2013 ) T_min = 0.85, T_max = 0.94
8928 measured reflections
3121 independent reflections
2579 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.090
S = 1.04
3121 reflections
246 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.88 (2)	2.04 (2)	2.9212 (17)	174.0 (18)
N2—H2⋯O2ⁱⁱ	0.920 (18)	1.988 (18)	2.9025 (16)	171.9 (15)
C4—H4⋯O3ⁱⁱⁱ	0.95	2.50	3.410 (2)	161
C11—H11B⋯N3	0.99	2.36	2.8373 (19)	109
C20—H20A⋯O1^iv	0.98	2.49	3.215 (2)	131
Symmetry codes: (i) -x+2, -y+1, -z+2; (ii) -x+2, -y+2, -z+2; (iii) x+1, y-1, z; (iv) x-1, y, z.

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 964356

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813027050/sj5357sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813027050/sj5357Isup2.hkl

checkCIF report

Comment top

Indomethacin like other non-steroidal anti-inflammatory drugs (NSAIDs) is widely used in treatment of pain, fever, and inflammation (Richy et al., 2004). Prolonged administration of such drugs is commonly associated with several undesired side-effects. The most common of these are gastrointestinal hemorrhage, ulceration, and decreased renal function (Allison et al., 1992; McMahon 2001; Rocha et al., 2001). The existence of a free carboxylic acid group in the parent drug has been considred to be the major factor in establishing superficial stomach erosion, particularly in the corpus region of the stomach (Halen et al., 2009). Thus, it was considered essential to mask or to remove this functional group in order to produce a safer and more tolerant prodrug profile. Following this reasoning, we report here the synthesis and crystal structure of the title compound.

The "J" shaped conformation of the title molecule (I) is shown in Fig. 1. The bond lengths and bond angles of (I) compare well with those in related compounds (Mague et al., 2013).

In the crystal, the molecules form inversion dimers with R₂²(8) motifs (Bernstein et al., 1995) through N—H···O hydrogen bonds (Fig. 2, Table 1). In addition, the dimers are linked by C—H···O and N—H···O hydrogen bonds (Table 1), forming a three-dimensional network.

Related literature top

For general medical applications of non-steriodal anti-inflammatory drugs (NSAIDs), see: Richy et al. (2004). For the undesirable side effects of such drugs, see: Allison et al. (1992); McMahon (2001); Rocha et al. (2001); Halen et al. (2009). For a similar structure, see: Mague et al. (2013). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A mixture of 233 mg (1 mmol) 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetohydrazide and 136 mg (1 mmol) of 4-methoxybenzaldehyde in 30 ml ethanol containing few drops of glacial acetic acid was refluxed for 5 h. The reaction mixture was allowed to cool to room temperature and the excess solvent was evaporated under vacuum. The residual solid was collected, washed with cold ethanol and recrystallized from ethanol. Colourless blocks of X-ray quality were obtained. M.p. 453–455 K.

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Perspective view of the title compound with 50% probability displacement ellipsoids.
	Fig. 2. Packing viewed along a showing the hydrogen bonds as dotted lines.

N'-[(E)-4-Methoxybenzylidene]-2-(5-methoxy-2-methyl-1H-indol-3-yl)-acetohydrazide top

Crystal data top

C₂₀H₂₁N₃O₃	Z = 2
M_r = 351.40	F(000) = 372
Triclinic, P1	D_x = 1.336 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 7.1894 (2) Å	Cell parameters from 6305 reflections
b = 10.4055 (3) Å	θ = 3.8–68.2°
c = 12.4403 (4) Å	µ = 0.74 mm⁻¹
α = 107.983 (2)°	T = 100 K
β = 92.451 (2)°	Block, colourless
γ = 97.882 (2)°	0.14 × 0.12 × 0.08 mm
V = 873.24 (5) Å³

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3121 independent reflections
Radiation source: INCOATEC IµS micro–focus source	2579 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.029
Detector resolution: 10.4167 pixels mm^-1	θ_max = 68.2°, θ_min = 3.8°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −11→12
T_min = 0.85, T_max = 0.94	l = −14→12
8928 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.036	w = 1/[Σ²(F_o²) + (0.0398P)² + 0.2493P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.090	(Δ/σ)_max = 0.001
S = 1.04	Δρ_max = 0.19 e Å⁻³
3121 reflections	Δρ_min = −0.18 e Å⁻³
246 parameters

Crystal data top

C₂₀H₂₁N₃O₃	γ = 97.882 (2)°
M_r = 351.40	V = 873.24 (5) Å³
Triclinic, P1	Z = 2
a = 7.1894 (2) Å	Cu Kα radiation
b = 10.4055 (3) Å	µ = 0.74 mm⁻¹
c = 12.4403 (4) Å	T = 100 K
α = 107.983 (2)°	0.14 × 0.12 × 0.08 mm
β = 92.451 (2)°

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3121 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2013)	2579 reflections with I > 2σ(I)
T_min = 0.85, T_max = 0.94	R_int = 0.029
8928 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.19 e Å⁻³
3121 reflections	Δρ_min = −0.18 e Å⁻³
246 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
O1	0.71418 (17)	0.52381 (11)	0.54515 (9)	0.0430 (4)
O2	0.98707 (13)	0.84392 (9)	1.03898 (8)	0.0292 (3)
O3	−0.13304 (14)	0.95693 (11)	0.60125 (9)	0.0371 (3)
N1	0.79353 (17)	0.35490 (13)	0.91900 (12)	0.0351 (4)
N2	0.76381 (16)	0.90476 (12)	0.94351 (10)	0.0260 (3)
N3	0.58416 (16)	0.88308 (12)	0.89050 (9)	0.0265 (3)
C1	0.7349 (3)	0.44162 (19)	0.43283 (14)	0.0480 (6)
C2	0.7324 (2)	0.46796 (15)	0.63133 (13)	0.0345 (5)
C3	0.7787 (2)	0.33672 (16)	0.61512 (15)	0.0388 (5)
C4	0.7991 (2)	0.28921 (15)	0.70661 (15)	0.0384 (5)
C5	0.7752 (2)	0.37351 (15)	0.81367 (14)	0.0326 (4)
C6	0.72832 (19)	0.50583 (14)	0.83158 (13)	0.0296 (4)
C7	0.7039 (2)	0.55117 (15)	0.73782 (13)	0.0310 (4)
C8	0.7797 (2)	0.48079 (17)	1.12353 (14)	0.0379 (5)
C9	0.76673 (19)	0.47320 (15)	1.00178 (14)	0.0317 (5)
C10	0.72383 (19)	0.56677 (14)	0.95159 (12)	0.0281 (4)
C11	0.67910 (19)	0.70663 (14)	1.01121 (12)	0.0284 (4)
C12	0.82053 (19)	0.82164 (14)	0.99829 (11)	0.0256 (4)
C13	0.5515 (2)	0.97217 (14)	0.84341 (11)	0.0272 (4)
C14	0.3702 (2)	0.96285 (14)	0.78169 (11)	0.0269 (4)
C15	0.2179 (2)	0.86146 (14)	0.77499 (12)	0.0290 (4)
C16	0.0484 (2)	0.85462 (15)	0.71417 (12)	0.0302 (4)
C17	0.0283 (2)	0.95182 (15)	0.66076 (12)	0.0296 (4)
C18	0.1787 (2)	1.05399 (15)	0.66754 (12)	0.0322 (5)
C19	0.3475 (2)	1.05862 (15)	0.72627 (12)	0.0305 (5)
C20	−0.2801 (2)	0.84238 (17)	0.57471 (14)	0.0380 (5)
H1	0.855 (3)	0.295 (2)	0.9360 (16)	0.052 (5)*
H1A	0.86220	0.41770	0.42890	0.0720*
H1B	0.71490	0.49270	0.38010	0.0720*
H1C	0.64190	0.35780	0.41200	0.0720*
H2	0.847 (2)	0.9799 (18)	0.9426 (14)	0.037 (4)*
H3	0.79600	0.28050	0.54110	0.0470*
H4	0.82900	0.20030	0.69610	0.0460*
H7	0.66820	0.63830	0.74730	0.0370*
H8A	0.66310	0.43210	1.13970	0.0570*
H8B	0.79780	0.57680	1.17140	0.0570*
H8C	0.88670	0.43840	1.13960	0.0570*
H11A	0.67420	0.71790	1.09300	0.0340*
H11B	0.55260	0.71370	0.98090	0.0340*
H13	0.64810	1.04650	0.84880	0.0330*
H15	0.23020	0.79590	0.81260	0.0350*
H16	−0.05350	0.78380	0.70910	0.0360*
H18	0.16500	1.12090	0.63150	0.0390*
H19	0.45010	1.12800	0.72920	0.0370*
H20A	−0.23210	0.75960	0.53170	0.0570*
H20B	−0.38450	0.85740	0.52910	0.0570*
H20C	−0.32500	0.83130	0.64510	0.0570*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0543 (7)	0.0399 (6)	0.0312 (6)	0.0116 (5)	0.0040 (5)	0.0044 (5)
O2	0.0263 (5)	0.0249 (5)	0.0361 (5)	0.0024 (4)	−0.0050 (4)	0.0112 (4)
O3	0.0322 (6)	0.0354 (6)	0.0412 (6)	0.0052 (5)	−0.0101 (5)	0.0103 (5)
N1	0.0263 (7)	0.0250 (7)	0.0565 (9)	0.0034 (5)	−0.0021 (6)	0.0177 (6)
N2	0.0243 (6)	0.0238 (6)	0.0290 (6)	0.0014 (5)	−0.0035 (5)	0.0091 (5)
N3	0.0257 (6)	0.0267 (6)	0.0251 (6)	0.0044 (5)	−0.0018 (5)	0.0060 (5)
C1	0.0488 (11)	0.0495 (10)	0.0348 (9)	0.0063 (8)	0.0034 (8)	−0.0016 (8)
C2	0.0298 (8)	0.0309 (8)	0.0389 (8)	0.0030 (6)	0.0015 (6)	0.0063 (7)
C3	0.0322 (8)	0.0288 (8)	0.0469 (9)	0.0022 (6)	0.0044 (7)	0.0007 (7)
C4	0.0269 (8)	0.0232 (8)	0.0604 (11)	0.0041 (6)	0.0038 (7)	0.0064 (7)
C5	0.0217 (7)	0.0253 (7)	0.0494 (9)	0.0010 (6)	−0.0006 (6)	0.0117 (7)
C6	0.0201 (7)	0.0245 (7)	0.0421 (8)	0.0007 (5)	−0.0014 (6)	0.0093 (6)
C7	0.0271 (8)	0.0257 (7)	0.0383 (8)	0.0038 (6)	−0.0007 (6)	0.0079 (6)
C8	0.0301 (8)	0.0363 (9)	0.0516 (10)	−0.0003 (6)	−0.0071 (7)	0.0240 (8)
C9	0.0199 (7)	0.0287 (8)	0.0469 (9)	−0.0017 (6)	−0.0035 (6)	0.0159 (7)
C10	0.0212 (7)	0.0250 (7)	0.0388 (8)	0.0006 (5)	−0.0021 (6)	0.0131 (6)
C11	0.0266 (7)	0.0280 (8)	0.0312 (7)	0.0028 (6)	−0.0002 (6)	0.0113 (6)
C12	0.0275 (8)	0.0227 (7)	0.0246 (7)	0.0053 (6)	0.0004 (6)	0.0044 (6)
C13	0.0298 (8)	0.0240 (7)	0.0266 (7)	0.0031 (6)	0.0004 (6)	0.0072 (6)
C14	0.0297 (8)	0.0257 (7)	0.0237 (7)	0.0063 (6)	0.0006 (6)	0.0049 (6)
C15	0.0323 (8)	0.0250 (7)	0.0301 (7)	0.0063 (6)	0.0008 (6)	0.0089 (6)
C16	0.0284 (8)	0.0257 (7)	0.0336 (8)	0.0026 (6)	0.0015 (6)	0.0060 (6)
C17	0.0296 (8)	0.0303 (8)	0.0264 (7)	0.0094 (6)	−0.0022 (6)	0.0042 (6)
C18	0.0362 (8)	0.0313 (8)	0.0316 (8)	0.0066 (6)	−0.0019 (6)	0.0136 (7)
C19	0.0298 (8)	0.0301 (8)	0.0316 (8)	0.0026 (6)	−0.0004 (6)	0.0111 (6)
C20	0.0293 (8)	0.0443 (9)	0.0367 (8)	0.0029 (7)	−0.0040 (6)	0.0098 (7)

Geometric parameters (Å, º) top

O1—C1	1.422 (2)	C14—C15	1.393 (2)
O1—C2	1.3776 (19)	C15—C16	1.388 (2)
O2—C12	1.2422 (17)	C16—C17	1.390 (2)
O3—C17	1.3653 (18)	C17—C18	1.389 (2)
O3—C20	1.425 (2)	C18—C19	1.377 (2)
N1—C5	1.386 (2)	C1—H1A	0.9800
N1—C9	1.383 (2)	C1—H1B	0.9800
N2—N3	1.3818 (16)	C1—H1C	0.9800
N2—C12	1.3475 (19)	C3—H3	0.9500
N3—C13	1.2810 (19)	C4—H4	0.9500
N1—H1	0.88 (2)	C7—H7	0.9500
N2—H2	0.920 (18)	C8—H8A	0.9800
C2—C3	1.406 (2)	C8—H8B	0.9800
C2—C7	1.382 (2)	C8—H8C	0.9800
C3—C4	1.384 (2)	C11—H11A	0.9900
C4—C5	1.383 (2)	C11—H11B	0.9900
C5—C6	1.415 (2)	C13—H13	0.9500
C6—C10	1.434 (2)	C15—H15	0.9500
C6—C7	1.400 (2)	C16—H16	0.9500
C8—C9	1.490 (2)	C18—H18	0.9500
C9—C10	1.369 (2)	C19—H19	0.9500
C10—C11	1.501 (2)	C20—H20A	0.9800
C11—C12	1.514 (2)	C20—H20B	0.9800
C13—C14	1.460 (2)	C20—H20C	0.9800
C14—C19	1.398 (2)

C1—O1—C2	118.05 (13)	C14—C19—C18	121.03 (14)
C17—O3—C20	117.85 (13)	O1—C1—H1A	109.00
C5—N1—C9	109.09 (13)	O1—C1—H1B	109.00
N3—N2—C12	122.52 (12)	O1—C1—H1C	109.00
N2—N3—C13	114.94 (12)	H1A—C1—H1B	109.00
C9—N1—H1	120.9 (12)	H1A—C1—H1C	109.00
C5—N1—H1	126.0 (13)	H1B—C1—H1C	109.00
N3—N2—H2	118.7 (10)	C2—C3—H3	120.00
C12—N2—H2	118.8 (10)	C4—C3—H3	120.00
O1—C2—C3	123.67 (14)	C3—C4—H4	121.00
O1—C2—C7	115.23 (14)	C5—C4—H4	121.00
C3—C2—C7	121.10 (15)	C2—C7—H7	120.00
C2—C3—C4	120.20 (16)	C6—C7—H7	120.00
C3—C4—C5	118.84 (15)	C9—C8—H8A	109.00
C4—C5—C6	121.74 (15)	C9—C8—H8B	109.00
N1—C5—C6	107.17 (14)	C9—C8—H8C	110.00
N1—C5—C4	131.07 (15)	H8A—C8—H8B	109.00
C5—C6—C10	107.06 (13)	H8A—C8—H8C	109.00
C7—C6—C10	134.17 (14)	H8B—C8—H8C	109.00
C5—C6—C7	118.73 (14)	C10—C11—H11A	109.00
C2—C7—C6	119.35 (15)	C10—C11—H11B	109.00
N1—C9—C8	120.08 (14)	C12—C11—H11A	109.00
N1—C9—C10	109.40 (14)	C12—C11—H11B	109.00
C8—C9—C10	130.47 (15)	H11A—C11—H11B	108.00
C6—C10—C11	126.49 (13)	N3—C13—H13	119.00
C9—C10—C11	126.29 (13)	C14—C13—H13	119.00
C6—C10—C9	107.22 (13)	C14—C15—H15	119.00
C10—C11—C12	113.58 (12)	C16—C15—H15	119.00
N2—C12—C11	119.29 (12)	C15—C16—H16	120.00
O2—C12—N2	118.72 (13)	C17—C16—H16	120.00
O2—C12—C11	121.97 (13)	C17—C18—H18	120.00
N3—C13—C14	121.97 (13)	C19—C18—H18	120.00
C13—C14—C19	119.12 (13)	C14—C19—H19	119.00
C15—C14—C19	118.23 (13)	C18—C19—H19	119.00
C13—C14—C15	122.65 (13)	O3—C20—H20A	110.00
C14—C15—C16	121.06 (14)	O3—C20—H20B	109.00
C15—C16—C17	119.73 (14)	O3—C20—H20C	109.00
O3—C17—C16	124.68 (14)	H20A—C20—H20B	109.00
C16—C17—C18	119.73 (13)	H20A—C20—H20C	109.00
O3—C17—C18	115.59 (14)	H20B—C20—H20C	109.00
C17—C18—C19	120.21 (15)

C1—O1—C2—C3	3.0 (2)	C10—C6—C7—C2	174.92 (15)
C1—O1—C2—C7	−177.73 (15)	C7—C6—C10—C9	−177.33 (16)
C20—O3—C17—C18	169.28 (13)	C5—C6—C7—C2	−2.2 (2)
C20—O3—C17—C16	−11.6 (2)	C5—C6—C10—C9	0.04 (16)
C9—N1—C5—C6	−2.29 (16)	C8—C9—C10—C11	0.6 (3)
C5—N1—C9—C10	2.37 (17)	N1—C9—C10—C6	−1.46 (16)
C9—N1—C5—C4	176.09 (16)	N1—C9—C10—C11	178.14 (13)
C5—N1—C9—C8	−179.76 (13)	C8—C9—C10—C6	−179.03 (15)
C12—N2—N3—C13	179.16 (13)	C6—C10—C11—C12	−64.10 (18)
N3—N2—C12—C11	−5.17 (19)	C9—C10—C11—C12	116.38 (16)
N3—N2—C12—O2	176.44 (12)	C10—C11—C12—O2	−65.23 (17)
N2—N3—C13—C14	178.67 (12)	C10—C11—C12—N2	116.43 (14)
O1—C2—C3—C4	178.35 (14)	N3—C13—C14—C19	−176.06 (13)
C7—C2—C3—C4	−0.9 (2)	N3—C13—C14—C15	3.6 (2)
C3—C2—C7—C6	2.4 (2)	C13—C14—C19—C18	−179.70 (13)
O1—C2—C7—C6	−176.95 (13)	C15—C14—C19—C18	0.7 (2)
C2—C3—C4—C5	−0.7 (2)	C13—C14—C15—C16	−179.08 (13)
C3—C4—C5—N1	−177.38 (15)	C19—C14—C15—C16	0.6 (2)
C3—C4—C5—C6	0.8 (2)	C14—C15—C16—C17	−1.3 (2)
N1—C5—C6—C7	179.22 (13)	C15—C16—C17—C18	0.8 (2)
C4—C5—C6—C7	0.7 (2)	C15—C16—C17—O3	−178.29 (13)
C4—C5—C6—C10	−177.19 (14)	O3—C17—C18—C19	179.57 (13)
N1—C5—C6—C10	1.37 (16)	C16—C17—C18—C19	0.4 (2)
C7—C6—C10—C11	3.1 (3)	C17—C18—C19—C14	−1.2 (2)
C5—C6—C10—C11	−179.56 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.88 (2)	2.04 (2)	2.9212 (17)	174.0 (18)
N2—H2···O2ⁱⁱ	0.920 (18)	1.988 (18)	2.9025 (16)	171.9 (15)
C4—H4···O3ⁱⁱⁱ	0.95	2.50	3.410 (2)	161
C11—H11B···N3	0.99	2.36	2.8373 (19)	109
C20—H20A···O1^iv	0.98	2.49	3.215 (2)	131

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.88 (2)	2.04 (2)	2.9212 (17)	174.0 (18)
N2—H2···O2ⁱⁱ	0.920 (18)	1.988 (18)	2.9025 (16)	171.9 (15)
C4—H4···O3ⁱⁱⁱ	0.9500	2.5000	3.410 (2)	161.00
C11—H11B···N3	0.9900	2.3600	2.8373 (19)	109.00
C20—H20A···O1^iv	0.9800	2.4900	3.215 (2)	131.00

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

Acknowledgements

The authors are deeply grateful to Tulane University, Erciyes University and Manchester Metropolitan University for supporting this study.

References

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Volume 69| Part 11| November 2013| Pages o1660-o1661

doi:10.1107/S1600536813027050

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

N′-[(E)-4-Meth­­oxy­benzyl­­idene]-2-(5-meth­­oxy-2-methyl-1H-indol-3-yl)acetohydrazide

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organic compounds

N′-[(E)-4-Methoxybenzylidene]-2-(5-methoxy-2-methyl-1H-indol-3-yl)acetohydrazide