N'-[(E)-4-Meth-oxy-benzyl-idene]-2-(5-meth-oxy-2-methyl-1H-indol-3-yl)acetohydrazide.

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 intra-molecular C-H⋯N hydrogen bond. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, forming dimers with R 2 (2)(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.

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 = 351.40

Triclinic,

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[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.090

S = 1.04

3121 reflections

246 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.18 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813027050/sj5357sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H21N3O3	Z = 2
Mr = 351.40	F(000) = 372
Triclinic, P1	Dx = 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

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	Rint = 0.029
Detector resolution: 10.4167 pixels mm-1	θmax = 68.2°, θmin = 3.8°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −11→12
Tmin = 0.85, Tmax = 0.94	l = −14→12
8928 measured reflections

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(Fo2) + (0.0398P)2 + 0.2493P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.090	(Δ/σ)max = 0.001
S = 1.04	Δρmax = 0.19 e Å−3
3121 reflections	Δρmin = −0.18 e Å−3
246 parameters

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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···O1iv	0.98	2.49	3.215 (2)	131

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⋯O1iv	0.98	2.49	3.215 (2)	131

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .