Methyl (2Z)-2-[(2-formyl-3-methyl-1H-indol-1-yl)meth-yl]-3-(4-meth-oxy-phen-yl)prop-2-enoate.

In the title indole derivative, C22H21NO4, the dihedral angle between the benzene and pyrrole rings of indole moiety is 1.8 (1)°. The plane of the 4-meth-oxy-phenyl ring is oriented with a dihedral angle of 60.7 (1)° with respect to the plane of the indole moiety. The mol-ecular packing is stabilized by C-H⋯O hydrogen bonds which form a V-shaped chain arrangement along the bc plane of the unit cell. In addition to this, C-H⋯π and π-π inter-actions [centroid-centroid distances = 3.8102 (11) and 3.8803(12) Å], which run along the b-axis direction, stabilize the mol-ecular packing.

Related literature

For general background to indole derivatives, see: Kaushik et al. (2013 ▶); Singh et al. (2000 ▶); Andreani et al. (2001 ▶); Grinev et al. (1984 ▶); Rodriguez et al. (1985 ▶). For a related structure, see: Selvanayagam et al. (2008 ▶). For the superposition of a related structure, see: Gans & Shalloway (2001 ▶)

Experimental

Crystal data

C22H21NO4

M = 363.40

Monoclinic,

a = 12.6009 (13) Å

b = 10.7458 (11) Å

c = 14.8937 (16) Å

β = 111.954 (2)°

V = 1870.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 292 K

0.20 × 0.18 × 0.16 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

21494 measured reflections

4462 independent reflections

3214 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.143

S = 1.01

4462 reflections

247 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL2013 and PLATON.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814005261/zq2219sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814005261/zq2219Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814005261/zq2219Isup3.cml

CCDC reference: 990594

Additional supporting information: crystallographic information; 3D view; checkCIF report

C22H21NO4	F(000) = 768
Mr = 363.40	Dx = 1.290 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.6009 (13) Å	Cell parameters from 13428 reflections
b = 10.7458 (11) Å	θ = 2.2–27.7°
c = 14.8937 (16) Å	µ = 0.09 mm−1
β = 111.954 (2)°	T = 292 K
V = 1870.5 (3) Å3	Block, colourless
Z = 4	0.20 × 0.18 × 0.16 mm

Bruker SMART APEX CCD area-detector diffractometer	Rint = 0.030
Radiation source: fine-focus sealed tube	θmax = 28.0°, θmin = 1.8°
ω scans	h = −16→16
21494 measured reflections	k = −14→14
4462 independent reflections	l = −19→19
3214 reflections with I > 2σ(I)

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052	H-atom parameters constrained
wR(F2) = 0.143	w = 1/[σ2(Fo2) + (0.069P)2 + 0.3592P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
4462 reflections	Δρmax = 0.21 e Å−3
247 parameters	Δρmin = −0.15 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	1.09513 (15)	0.60014 (19)	0.38553 (11)	0.1024 (6)
O2	0.73093 (13)	0.23166 (15)	0.23313 (11)	0.0890 (5)
O3	0.83214 (11)	0.40122 (13)	0.29526 (9)	0.0682 (4)
O4	0.44555 (12)	0.52878 (12)	−0.32562 (9)	0.0700 (4)
N1	0.93920 (10)	0.46791 (12)	0.15072 (9)	0.0437 (3)
C1	0.97938 (13)	0.39988 (13)	0.09250 (12)	0.0453 (4)
C2	0.92204 (16)	0.35281 (16)	0.00003 (13)	0.0555 (4)
H2	0.8437	0.3640	−0.0321	0.067*
C3	0.9859 (2)	0.28912 (17)	−0.04190 (16)	0.0710 (6)
H3	0.9499	0.2570	−0.1039	0.085*
C4	1.1026 (2)	0.27130 (18)	0.00578 (19)	0.0789 (7)
H4	1.1428	0.2267	−0.0247	0.095*
C5	1.15958 (17)	0.31737 (18)	0.09595 (18)	0.0709 (6)
H5	1.2379	0.3047	0.1270	0.085*
C6	1.09796 (14)	0.38477 (15)	0.14165 (13)	0.0534 (4)
C7	1.12943 (14)	0.44737 (16)	0.23098 (13)	0.0559 (4)
C8	1.03115 (13)	0.49785 (15)	0.23520 (12)	0.0481 (4)
C9	1.24838 (17)	0.4581 (3)	0.30555 (18)	0.0886 (7)
H9A	1.2584	0.5388	0.3352	0.133*
H9B	1.3028	0.4471	0.2751	0.133*
H9C	1.2601	0.3952	0.3541	0.133*
C10	0.81868 (12)	0.50076 (14)	0.12346 (12)	0.0450 (3)
H10A	0.7900	0.5348	0.0584	0.054*
H10B	0.8118	0.5646	0.1670	0.054*
C11	0.74697 (12)	0.39005 (14)	0.12710 (12)	0.0469 (4)
C12	0.76846 (14)	0.33019 (18)	0.22202 (13)	0.0571 (4)
C13	0.8478 (2)	0.3602 (3)	0.39105 (15)	0.0955 (8)
H13A	0.7749	0.3565	0.3976	0.143*
H13B	0.8967	0.4176	0.4376	0.143*
H13C	0.8822	0.2791	0.4020	0.143*
C14	0.66281 (13)	0.34297 (16)	0.05107 (12)	0.0521 (4)
H14	0.6321	0.2685	0.0621	0.063*
C15	0.61153 (12)	0.39180 (15)	−0.04761 (12)	0.0483 (4)
C16	0.57841 (15)	0.31163 (16)	−0.12596 (13)	0.0573 (4)
H16	0.5927	0.2270	−0.1150	0.069*
C17	0.52504 (16)	0.35310 (17)	−0.21948 (13)	0.0588 (4)
H17	0.5059	0.2973	−0.2708	0.071*
C18	0.49998 (14)	0.47814 (16)	−0.23680 (12)	0.0514 (4)
C19	0.53108 (14)	0.55973 (15)	−0.15976 (13)	0.0530 (4)
H19	0.5147	0.6440	−0.1708	0.064*
C20	0.58585 (13)	0.51745 (15)	−0.06720 (12)	0.0508 (4)
H20	0.6064	0.5739	−0.0162	0.061*
C21	0.4105 (3)	0.4468 (2)	−0.40614 (16)	0.0957 (8)
H21A	0.4760	0.4035	−0.4086	0.144*
H21B	0.3751	0.4937	−0.4646	0.144*
H21C	0.3567	0.3877	−0.3996	0.144*
C22	1.01886 (18)	0.57581 (18)	0.30950 (14)	0.0651 (5)
H22	0.9471	0.6098	0.2981	0.078*

	U11	U22	U33	U12	U13	U23
O1	0.0958 (12)	0.1354 (16)	0.0626 (9)	−0.0236 (11)	0.0141 (8)	−0.0265 (9)
O2	0.0856 (10)	0.0859 (10)	0.0928 (11)	−0.0224 (8)	0.0304 (8)	0.0320 (8)
O3	0.0729 (8)	0.0836 (9)	0.0526 (7)	−0.0043 (7)	0.0284 (6)	0.0071 (6)
O4	0.0881 (9)	0.0592 (8)	0.0563 (8)	0.0043 (7)	0.0197 (7)	−0.0027 (6)
N1	0.0396 (6)	0.0444 (7)	0.0481 (7)	−0.0008 (5)	0.0174 (6)	0.0023 (5)
C1	0.0491 (8)	0.0369 (7)	0.0578 (9)	−0.0016 (6)	0.0290 (7)	0.0064 (7)
C2	0.0657 (10)	0.0494 (9)	0.0614 (10)	−0.0101 (8)	0.0351 (9)	−0.0008 (8)
C3	0.0993 (16)	0.0541 (11)	0.0823 (13)	−0.0183 (10)	0.0601 (12)	−0.0107 (9)
C4	0.1000 (17)	0.0518 (11)	0.1216 (19)	−0.0048 (10)	0.0836 (16)	−0.0062 (12)
C5	0.0616 (11)	0.0558 (11)	0.1150 (17)	0.0047 (9)	0.0556 (12)	0.0115 (11)
C6	0.0482 (9)	0.0452 (9)	0.0750 (12)	0.0008 (7)	0.0324 (8)	0.0135 (8)
C7	0.0436 (8)	0.0562 (10)	0.0655 (11)	−0.0032 (7)	0.0177 (8)	0.0156 (8)
C8	0.0448 (8)	0.0475 (8)	0.0499 (9)	−0.0061 (6)	0.0152 (7)	0.0068 (7)
C9	0.0472 (11)	0.1087 (18)	0.0958 (17)	−0.0028 (11)	0.0107 (10)	0.0148 (14)
C10	0.0420 (8)	0.0429 (8)	0.0502 (8)	0.0020 (6)	0.0173 (7)	0.0027 (7)
C11	0.0396 (8)	0.0479 (9)	0.0575 (10)	0.0023 (6)	0.0232 (7)	0.0046 (7)
C12	0.0454 (9)	0.0649 (11)	0.0660 (11)	0.0019 (8)	0.0266 (8)	0.0137 (9)
C13	0.0927 (16)	0.144 (2)	0.0604 (13)	0.0094 (15)	0.0402 (12)	0.0229 (14)
C14	0.0445 (8)	0.0483 (9)	0.0676 (11)	−0.0025 (7)	0.0255 (8)	0.0015 (8)
C15	0.0373 (7)	0.0489 (9)	0.0602 (10)	−0.0023 (6)	0.0201 (7)	−0.0044 (7)
C16	0.0573 (10)	0.0437 (9)	0.0696 (12)	−0.0010 (7)	0.0221 (9)	−0.0051 (8)
C17	0.0648 (11)	0.0505 (10)	0.0601 (11)	−0.0014 (8)	0.0220 (9)	−0.0133 (8)
C18	0.0484 (9)	0.0522 (9)	0.0554 (10)	0.0004 (7)	0.0215 (8)	−0.0047 (7)
C19	0.0497 (9)	0.0432 (8)	0.0661 (11)	0.0039 (7)	0.0216 (8)	−0.0042 (8)
C20	0.0442 (8)	0.0478 (9)	0.0598 (10)	0.0007 (7)	0.0186 (7)	−0.0122 (7)
C21	0.138 (2)	0.0762 (15)	0.0564 (12)	0.0015 (14)	0.0173 (13)	−0.0096 (11)
C22	0.0671 (11)	0.0654 (11)	0.0594 (11)	−0.0121 (9)	0.0198 (9)	−0.0061 (9)

O1—C22	1.209 (2)	C9—H9C	0.9600
O2—C12	1.196 (2)	C10—C11	1.507 (2)
O3—C12	1.327 (2)	C10—H10A	0.9700
O3—C13	1.435 (2)	C10—H10B	0.9700
O4—C18	1.356 (2)	C11—C14	1.328 (2)
O4—C21	1.419 (2)	C11—C12	1.483 (2)
N1—C1	1.3678 (19)	C13—H13A	0.9600
N1—C8	1.3926 (19)	C13—H13B	0.9600
N1—C10	1.4610 (18)	C13—H13C	0.9600
C1—C2	1.390 (2)	C14—C15	1.464 (2)
C1—C6	1.406 (2)	C14—H14	0.9300
C2—C3	1.371 (3)	C15—C16	1.383 (2)
C2—H2	0.9300	C15—C20	1.394 (2)
C3—C4	1.387 (3)	C16—C17	1.375 (2)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.358 (3)	C17—C18	1.382 (2)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.409 (3)	C18—C19	1.379 (2)
C5—H5	0.9300	C19—C20	1.368 (2)
C6—C7	1.409 (3)	C19—H19	0.9300
C7—C8	1.375 (2)	C20—H20	0.9300
C7—C9	1.499 (3)	C21—H21A	0.9600
C8—C22	1.442 (3)	C21—H21B	0.9600
C9—H9A	0.9600	C21—H21C	0.9600
C9—H9B	0.9600	C22—H22	0.9300
C12—O3—C13	117.18 (17)	C14—C11—C10	124.63 (15)
C18—O4—C21	117.36 (15)	C12—C11—C10	118.58 (14)
C1—N1—C8	108.43 (13)	O2—C12—O3	122.96 (17)
C1—N1—C10	123.07 (13)	O2—C12—C11	125.11 (18)
C8—N1—C10	128.50 (13)	O3—C12—C11	111.89 (15)
N1—C1—C2	130.12 (15)	O3—C13—H13A	109.5
N1—C1—C6	107.75 (14)	O3—C13—H13B	109.5
C2—C1—C6	122.11 (15)	H13A—C13—H13B	109.5
C3—C2—C1	117.19 (18)	O3—C13—H13C	109.5
C3—C2—H2	121.4	H13A—C13—H13C	109.5
C1—C2—H2	121.4	H13B—C13—H13C	109.5
C2—C3—C4	121.7 (2)	C11—C14—C15	129.15 (15)
C2—C3—H3	119.1	C11—C14—H14	115.4
C4—C3—H3	119.1	C15—C14—H14	115.4
C5—C4—C3	121.58 (18)	C16—C15—C20	116.97 (16)
C5—C4—H4	119.2	C16—C15—C14	120.29 (15)
C3—C4—H4	119.2	C20—C15—C14	122.56 (15)
C4—C5—C6	118.82 (19)	C17—C16—C15	122.12 (16)
C4—C5—H5	120.6	C17—C16—H16	118.9
C6—C5—H5	120.6	C15—C16—H16	118.9
C1—C6—C7	107.79 (14)	C16—C17—C18	119.69 (16)
C1—C6—C5	118.56 (18)	C16—C17—H17	120.2
C7—C6—C5	133.63 (18)	C18—C17—H17	120.2
C8—C7—C6	106.93 (14)	O4—C18—C19	116.06 (15)
C8—C7—C9	127.16 (19)	O4—C18—C17	124.70 (15)
C6—C7—C9	125.90 (18)	C19—C18—C17	119.24 (16)
C7—C8—N1	109.09 (15)	C20—C19—C18	120.44 (16)
C7—C8—C22	128.42 (16)	C20—C19—H19	119.8
N1—C8—C22	122.41 (15)	C18—C19—H19	119.8
C7—C9—H9A	109.5	C19—C20—C15	121.53 (15)
C7—C9—H9B	109.5	C19—C20—H20	119.2
H9A—C9—H9B	109.5	C15—C20—H20	119.2
C7—C9—H9C	109.5	O4—C21—H21A	109.5
H9A—C9—H9C	109.5	O4—C21—H21B	109.5
H9B—C9—H9C	109.5	H21A—C21—H21B	109.5
N1—C10—C11	111.97 (12)	O4—C21—H21C	109.5
N1—C10—H10A	109.2	H21A—C21—H21C	109.5
C11—C10—H10A	109.2	H21B—C21—H21C	109.5
N1—C10—H10B	109.2	O1—C22—C8	124.7 (2)
C11—C10—H10B	109.2	O1—C22—H22	117.7
H10A—C10—H10B	107.9	C8—C22—H22	117.7
C14—C11—C12	116.77 (15)
C8—N1—C1—C2	−177.30 (15)	C8—N1—C10—C11	−108.02 (17)
C10—N1—C1—C2	2.3 (2)	N1—C10—C11—C14	−117.11 (17)
C8—N1—C1—C6	1.06 (16)	N1—C10—C11—C12	64.62 (18)
C10—N1—C1—C6	−179.33 (12)	C13—O3—C12—O2	−5.0 (3)
N1—C1—C2—C3	178.78 (15)	C13—O3—C12—C11	172.89 (16)
C6—C1—C2—C3	0.6 (2)	C14—C11—C12—O2	13.9 (3)
C1—C2—C3—C4	0.4 (3)	C10—C11—C12—O2	−167.73 (18)
C2—C3—C4—C5	−0.8 (3)	C14—C11—C12—O3	−163.96 (15)
C3—C4—C5—C6	0.0 (3)	C10—C11—C12—O3	14.4 (2)
N1—C1—C6—C7	−0.97 (17)	C12—C11—C14—C15	170.52 (15)
C2—C1—C6—C7	177.54 (14)	C10—C11—C14—C15	−7.8 (3)
N1—C1—C6—C5	−179.87 (14)	C11—C14—C15—C16	142.41 (18)
C2—C1—C6—C5	−1.4 (2)	C11—C14—C15—C20	−42.6 (2)
C4—C5—C6—C1	1.0 (3)	C20—C15—C16—C17	1.6 (2)
C4—C5—C6—C7	−177.55 (18)	C14—C15—C16—C17	176.85 (16)
C1—C6—C7—C8	0.51 (17)	C15—C16—C17—C18	−2.0 (3)
C5—C6—C7—C8	179.17 (17)	C21—O4—C18—C19	−178.81 (19)
C1—C6—C7—C9	−178.39 (17)	C21—O4—C18—C17	1.0 (3)
C5—C6—C7—C9	0.3 (3)	C16—C17—C18—O4	−178.54 (16)
C6—C7—C8—N1	0.14 (17)	C16—C17—C18—C19	1.2 (3)
C9—C7—C8—N1	179.02 (17)	O4—C18—C19—C20	179.64 (15)
C6—C7—C8—C22	−176.54 (16)	C17—C18—C19—C20	−0.2 (2)
C9—C7—C8—C22	2.3 (3)	C18—C19—C20—C15	−0.2 (2)
C1—N1—C8—C7	−0.75 (17)	C16—C15—C20—C19	−0.4 (2)
C10—N1—C8—C7	179.66 (13)	C14—C15—C20—C19	−175.62 (14)
C1—N1—C8—C22	176.17 (14)	C7—C8—C22—O1	−6.8 (3)
C10—N1—C8—C22	−3.4 (2)	N1—C8—C22—O1	176.90 (19)
C1—N1—C10—C11	72.45 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1	0.96	2.53	3.033 (3)	113
C14—H14···O2	0.93	2.41	2.789 (2)	104
C10—H10B···O2i	0.97	2.51	3.480 (2)	173
C22—H22···O2i	0.93	2.49	3.409 (3)	171
C17—H17···Cg1ii	0.93	2.76	3.573 (2)	146
C21—H21A···Cg2ii	0.96	2.84	3.635 (3)	140

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N1/C1/C6–C8 and C1–C6 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O1	0.96	2.53	3.033 (3)	113
C14—H14⋯O2	0.93	2.41	2.789 (2)	104
C10—H10B⋯O2i	0.97	2.51	3.480 (2)	173
C22—H22⋯O2i	0.93	2.49	3.409 (3)	171
C17—H17⋯Cg1ii	0.93	2.76	3.573 (2)	146
C21—H21A⋯Cg2ii	0.96	2.84	3.635 (3)	140

Symmetry codes: (i) ; (ii) .