2-(5-Meth-oxy-2-methyl-1H-indol-3-yl)-N'-[(1E,2E)-3-phenyl-prop-2-en-1-yl-idene]acetohydrazide.

The title compound, C21H21N3O2, adopts a J-shaped conformation which 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 into R 2 (2)(8) and R 2 (2)(14) cyclic dimers, which form a chain running parallel to the b axis.

Related literature

For general background to side-effect toxicity of non-steroidal anti-inflammatory drugs (NSAIDs), see: Agrawal et al. (2010 ▶); Champion et al. (1997 ▶); Allan & Fletcher (1990 ▶). For reduction of GI toxicity attributed to NSAIDs, see: Halen et al. (2009 ▶); Schoen & Vender (1989 ▶); Mitchell & Warner (1999 ▶). For hydrogen-bond motifs, see: Etter et al. (1990 ▶).

Experimental

Crystal data

C21H21N3O2

M = 347.41

Triclinic,

a = 8.2786 (9) Å

b = 10.1194 (11) Å

c = 11.7739 (13) Å

α = 93.001 (2)°

β = 108.993 (2)°

γ = 105.578 (2)°

V = 887.76 (17) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 150 K

0.26 × 0.13 × 0.08 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.78, T max = 0.99

16303 measured reflections

4574 independent reflections

3675 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.126

S = 1.08

4574 reflections

245 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; 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, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813023805/qm2100sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813023805/qm2100Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813023805/qm2100Isup3.cml

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

C21H21N3O2	Z = 2
Mr = 347.41	F(000) = 368
Triclinic, P1	Dx = 1.300 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2786 (9) Å	Cell parameters from 8428 reflections
b = 10.1194 (11) Å	θ = 2.6–29.1°
c = 11.7739 (13) Å	µ = 0.09 mm−1
α = 93.001 (2)°	T = 150 K
β = 108.993 (2)°	Tablet, clear colourless
γ = 105.578 (2)°	0.26 × 0.13 × 0.08 mm
V = 887.76 (17) Å3

Bruker SMART APEX CCD diffractometer	4574 independent reflections
Radiation source: fine-focus sealed tube	3675 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Detector resolution: 8.3660 pixels mm-1	θmax = 29.1°, θmin = 1.9°
φ and ω scans	h = −11→10
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −13→13
Tmin = 0.78, Tmax = 0.99	l = −16→15
16303 measured reflections

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	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.126	W = 1/[Σ2(FO2) + (0.0677P)2 + 0.0983P] WHERE P = (FO2 + 2FC2)/3
S = 1.08	(Δ/σ)max = 0.001
4574 reflections	Δρmax = 0.36 e Å−3
245 parameters	Δρmin = −0.25 e Å−3
0 restraints

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = -30.00 and 210.00°. The scan time was 15 sec/frame.

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	0.28193 (13)	0.03509 (10)	0.57833 (8)	0.0383 (3)
O2	1.01220 (10)	0.33474 (8)	1.05582 (8)	0.0235 (3)
N1	0.76159 (13)	−0.14643 (9)	0.92901 (9)	0.0233 (3)
N2	0.76767 (12)	0.39782 (9)	0.96609 (9)	0.0198 (3)
N3	0.58483 (12)	0.37175 (9)	0.92778 (9)	0.0213 (3)
C1	0.1780 (2)	−0.04316 (16)	0.46126 (12)	0.0406 (4)
C2	0.40353 (16)	−0.01850 (12)	0.65687 (11)	0.0261 (3)
C3	0.44402 (17)	−0.13776 (12)	0.62313 (11)	0.0289 (3)
C4	0.56565 (16)	−0.18727 (11)	0.70752 (11)	0.0264 (3)
C5	0.64546 (14)	−0.11740 (10)	0.82602 (11)	0.0210 (3)
C6	0.61147 (14)	0.00623 (10)	0.85962 (10)	0.0190 (3)
C7	0.48756 (14)	0.05444 (11)	0.77385 (10)	0.0216 (3)
C8	0.92662 (16)	−0.04883 (12)	1.14821 (11)	0.0266 (3)
C9	0.80675 (14)	−0.04222 (11)	1.02468 (11)	0.0212 (3)
C10	0.71796 (14)	0.05319 (10)	0.98586 (10)	0.0190 (3)
C11	0.73269 (15)	0.18427 (10)	1.06001 (10)	0.0203 (3)
C12	0.84755 (14)	0.31009 (10)	1.02798 (10)	0.0184 (3)
C13	0.52187 (15)	0.45707 (11)	0.86269 (10)	0.0217 (3)
C14	0.33089 (15)	0.43345 (11)	0.81838 (11)	0.0235 (3)
C15	0.24928 (15)	0.51098 (12)	0.74611 (11)	0.0245 (3)
C16	0.05663 (15)	0.49356 (11)	0.70035 (10)	0.0223 (3)
C17	−0.06817 (16)	0.38488 (12)	0.72362 (11)	0.0257 (3)
C18	−0.24894 (16)	0.37336 (13)	0.68079 (11)	0.0289 (3)
C19	−0.30851 (17)	0.47052 (15)	0.61408 (12)	0.0342 (4)
C20	−0.18776 (18)	0.57806 (15)	0.58911 (12)	0.0350 (4)
C21	−0.00671 (17)	0.58889 (13)	0.63135 (11)	0.0291 (3)
H1	0.827 (2)	−0.2041 (17)	0.9322 (15)	0.044 (4)*
H1A	0.25730	−0.05190	0.41690	0.0610*
H1B	0.09370	0.00410	0.41640	0.0610*
H1C	0.11120	−0.13570	0.46960	0.0610*
H2	0.838 (2)	0.4754 (16)	0.9519 (13)	0.032 (4)*
H3	0.38760	−0.18480	0.54180	0.0350*
H4	0.59380	−0.26740	0.68470	0.0320*
H7	0.46140	0.13600	0.79550	0.0260*
H8A	0.98240	0.04490	1.19500	0.0400*
H8B	1.02000	−0.08780	1.14140	0.0400*
H8C	0.85640	−0.10790	1.18960	0.0400*
H11A	0.78640	0.17950	1.14750	0.0240*
H11B	0.61160	0.19340	1.04460	0.0240*
H13	0.59940	0.53380	0.84430	0.0260*
H14	0.25880	0.35810	0.84210	0.0280*
H15	0.32320	0.58470	0.72200	0.0290*
H17	−0.02820	0.31800	0.76950	0.0310*
H18	−0.33210	0.29880	0.69720	0.0350*
H19	−0.43240	0.46330	0.58550	0.0410*
H20	−0.22870	0.64450	0.54300	0.0420*
H21	0.07530	0.66240	0.61290	0.0350*

	U11	U22	U33	U12	U13	U23
O1	0.0382 (5)	0.0443 (5)	0.0258 (5)	0.0207 (4)	−0.0034 (4)	0.0015 (4)
O2	0.0174 (4)	0.0182 (4)	0.0346 (5)	0.0081 (3)	0.0066 (3)	0.0048 (3)
N1	0.0215 (5)	0.0171 (4)	0.0333 (5)	0.0093 (4)	0.0093 (4)	0.0057 (4)
N2	0.0159 (4)	0.0161 (4)	0.0280 (5)	0.0064 (3)	0.0072 (4)	0.0047 (4)
N3	0.0161 (4)	0.0197 (4)	0.0277 (5)	0.0069 (3)	0.0064 (4)	0.0016 (4)
C1	0.0359 (8)	0.0526 (8)	0.0244 (7)	0.0121 (6)	0.0006 (6)	0.0028 (6)
C2	0.0228 (6)	0.0271 (5)	0.0261 (6)	0.0082 (4)	0.0052 (5)	0.0048 (5)
C3	0.0302 (6)	0.0265 (6)	0.0257 (6)	0.0048 (5)	0.0083 (5)	−0.0029 (5)
C4	0.0277 (6)	0.0190 (5)	0.0338 (7)	0.0063 (4)	0.0138 (5)	0.0002 (4)
C5	0.0181 (5)	0.0161 (5)	0.0297 (6)	0.0054 (4)	0.0095 (4)	0.0040 (4)
C6	0.0162 (5)	0.0162 (4)	0.0252 (6)	0.0045 (4)	0.0084 (4)	0.0034 (4)
C7	0.0201 (5)	0.0191 (5)	0.0264 (6)	0.0074 (4)	0.0078 (5)	0.0041 (4)
C8	0.0227 (6)	0.0250 (5)	0.0329 (6)	0.0098 (4)	0.0076 (5)	0.0126 (5)
C9	0.0174 (5)	0.0180 (5)	0.0285 (6)	0.0057 (4)	0.0075 (4)	0.0071 (4)
C10	0.0165 (5)	0.0163 (4)	0.0244 (5)	0.0054 (4)	0.0068 (4)	0.0048 (4)
C11	0.0210 (5)	0.0183 (5)	0.0227 (5)	0.0075 (4)	0.0076 (4)	0.0044 (4)
C12	0.0190 (5)	0.0159 (4)	0.0206 (5)	0.0075 (4)	0.0059 (4)	0.0004 (4)
C13	0.0205 (5)	0.0191 (5)	0.0265 (6)	0.0085 (4)	0.0076 (5)	0.0024 (4)
C14	0.0199 (5)	0.0220 (5)	0.0278 (6)	0.0080 (4)	0.0065 (5)	0.0021 (4)
C15	0.0204 (5)	0.0242 (5)	0.0301 (6)	0.0088 (4)	0.0084 (5)	0.0059 (4)
C16	0.0212 (5)	0.0248 (5)	0.0223 (5)	0.0115 (4)	0.0059 (4)	0.0019 (4)
C17	0.0239 (6)	0.0260 (5)	0.0281 (6)	0.0116 (4)	0.0071 (5)	0.0043 (5)
C18	0.0230 (6)	0.0335 (6)	0.0282 (6)	0.0074 (5)	0.0082 (5)	0.0003 (5)
C19	0.0224 (6)	0.0487 (8)	0.0317 (7)	0.0172 (5)	0.0049 (5)	0.0051 (6)
C20	0.0320 (7)	0.0429 (7)	0.0341 (7)	0.0226 (6)	0.0066 (6)	0.0131 (6)
C21	0.0272 (6)	0.0319 (6)	0.0307 (6)	0.0136 (5)	0.0089 (5)	0.0095 (5)

O1—C1	1.4195 (17)	C16—C17	1.3991 (17)
O1—C2	1.3793 (16)	C17—C18	1.384 (2)
O2—C12	1.2432 (15)	C18—C19	1.3842 (19)
N1—C5	1.3824 (16)	C19—C20	1.382 (2)
N1—C9	1.3822 (15)	C20—C21	1.388 (2)
N2—N3	1.3758 (15)	C1—H1A	0.9800
N2—C12	1.3512 (15)	C1—H1B	0.9800
N3—C13	1.2866 (15)	C1—H1C	0.9800
N1—H1	0.891 (18)	C3—H3	0.9500
N2—H2	0.903 (16)	C4—H4	0.9500
C2—C7	1.3856 (16)	C7—H7	0.9500
C2—C3	1.4073 (18)	C8—H8A	0.9800
C3—C4	1.3871 (18)	C8—H8B	0.9800
C4—C5	1.3888 (17)	C8—H8C	0.9800
C5—C6	1.4179 (15)	C11—H11A	0.9900
C6—C10	1.4354 (16)	C11—H11B	0.9900
C6—C7	1.3986 (16)	C13—H13	0.9500
C8—C9	1.4869 (17)	C14—H14	0.9500
C9—C10	1.3748 (16)	C15—H15	0.9500
C10—C11	1.5030 (15)	C17—H17	0.9500
C11—C12	1.5169 (15)	C18—H18	0.9500
C13—C14	1.4409 (19)	C19—H19	0.9500
C14—C15	1.3328 (17)	C20—H20	0.9500
C15—C16	1.4645 (19)	C21—H21	0.9500
C16—C21	1.3936 (17)
C1—O1—C2	117.79 (11)	C16—C21—C20	121.01 (13)
C5—N1—C9	109.03 (9)	O1—C1—H1A	109.00
N3—N2—C12	121.25 (9)	O1—C1—H1B	109.00
N2—N3—C13	116.02 (10)	O1—C1—H1C	109.00
C9—N1—H1	121.1 (11)	H1A—C1—H1B	109.00
C5—N1—H1	127.1 (11)	H1A—C1—H1C	109.00
N3—N2—H2	120.7 (11)	H1B—C1—H1C	109.00
C12—N2—H2	118.1 (11)	C2—C3—H3	120.00
O1—C2—C3	123.67 (11)	C4—C3—H3	120.00
O1—C2—C7	115.35 (11)	C3—C4—H4	121.00
C3—C2—C7	120.98 (12)	C5—C4—H4	121.00
C2—C3—C4	120.58 (11)	C2—C7—H7	121.00
C3—C4—C5	118.66 (11)	C6—C7—H7	120.00
C4—C5—C6	121.15 (11)	C9—C8—H8A	109.00
N1—C5—C6	107.51 (10)	C9—C8—H8B	109.00
N1—C5—C4	131.34 (10)	C9—C8—H8C	109.00
C5—C6—C10	106.84 (10)	H8A—C8—H8B	109.00
C7—C6—C10	133.62 (10)	H8A—C8—H8C	109.00
C5—C6—C7	119.50 (10)	H8B—C8—H8C	109.00
C2—C7—C6	119.01 (11)	C10—C11—H11A	109.00
N1—C9—C8	120.64 (10)	C10—C11—H11B	109.00
N1—C9—C10	109.46 (10)	C12—C11—H11A	109.00
C8—C9—C10	129.81 (11)	C12—C11—H11B	109.00
C6—C10—C11	126.11 (10)	H11A—C11—H11B	108.00
C9—C10—C11	126.77 (10)	N3—C13—H13	121.00
C6—C10—C9	107.10 (10)	C14—C13—H13	121.00
C10—C11—C12	110.76 (10)	C13—C14—H14	118.00
N2—C12—C11	118.76 (11)	C15—C14—H14	118.00
O2—C12—N2	118.88 (10)	C14—C15—H15	117.00
O2—C12—C11	122.36 (10)	C16—C15—H15	117.00
N3—C13—C14	118.40 (11)	C16—C17—H17	119.00
C13—C14—C15	123.95 (11)	C18—C17—H17	120.00
C14—C15—C16	126.31 (11)	C17—C18—H18	120.00
C15—C16—C17	122.69 (11)	C19—C18—H18	120.00
C15—C16—C21	119.29 (11)	C18—C19—H19	120.00
C17—C16—C21	118.02 (12)	C20—C19—H19	120.00
C16—C17—C18	121.03 (11)	C19—C20—H20	120.00
C17—C18—C19	119.96 (12)	C21—C20—H20	120.00
C18—C19—C20	119.99 (14)	C16—C21—H21	119.00
C19—C20—C21	119.99 (13)	C20—C21—H21	120.00
C1—O1—C2—C3	7.23 (19)	C5—C6—C10—C11	176.91 (11)
C1—O1—C2—C7	−173.47 (12)	C7—C6—C10—C9	176.05 (13)
C9—N1—C5—C4	178.38 (13)	C7—C6—C10—C11	−5.5 (2)
C9—N1—C5—C6	−2.32 (13)	N1—C9—C10—C6	0.16 (14)
C5—N1—C9—C8	178.24 (11)	N1—C9—C10—C11	−178.30 (11)
C5—N1—C9—C10	1.36 (14)	C8—C9—C10—C6	−176.35 (12)
C12—N2—N3—C13	−175.51 (10)	C8—C9—C10—C11	5.2 (2)
N3—N2—C12—O2	176.74 (10)	C6—C10—C11—C12	−74.62 (15)
N3—N2—C12—C11	−2.72 (16)	C9—C10—C11—C12	103.55 (13)
N2—N3—C13—C14	179.00 (10)	C10—C11—C12—O2	−70.23 (14)
O1—C2—C3—C4	−178.89 (12)	C10—C11—C12—N2	109.21 (12)
C7—C2—C3—C4	1.8 (2)	N3—C13—C14—C15	−177.08 (12)
O1—C2—C7—C6	179.33 (11)	C13—C14—C15—C16	−178.72 (11)
C3—C2—C7—C6	−1.35 (19)	C14—C15—C16—C17	−3.5 (2)
C2—C3—C4—C5	0.5 (2)	C14—C15—C16—C21	176.09 (12)
C3—C4—C5—N1	175.97 (13)	C15—C16—C17—C18	178.73 (11)
C3—C4—C5—C6	−3.25 (19)	C21—C16—C17—C18	−0.85 (18)
N1—C5—C6—C7	−175.64 (11)	C15—C16—C21—C20	−178.26 (12)
N1—C5—C6—C10	2.37 (13)	C17—C16—C21—C20	1.33 (18)
C4—C5—C6—C7	3.75 (18)	C16—C17—C18—C19	−0.17 (19)
C4—C5—C6—C10	−178.25 (11)	C17—C18—C19—C20	0.7 (2)
C5—C6—C7—C2	−1.38 (17)	C18—C19—C20—C21	−0.3 (2)
C10—C6—C7—C2	−178.75 (13)	C19—C20—C21—C16	−0.8 (2)
C5—C6—C10—C9	−1.55 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.891 (18)	2.093 (18)	2.9841 (14)	178.1 (9)
N2—H2···O2ii	0.903 (16)	2.012 (16)	2.9055 (13)	170.0 (14)
C7—H7···N3	0.95	2.54	3.3609 (15)	145
C11—H11B···N3	0.99	2.34	2.7996 (15)	107

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.891 (18)	2.093 (18)	2.9841 (14)	178.1 (9)
N2—H2⋯O2ii	0.903 (16)	2.012 (16)	2.9055 (13)	170.0 (14)
C7—H7⋯N3	0.95	2.54	3.3609 (15)	145

Symmetry codes: (i) ; (ii) .