Crystal structure of methyl (2Z)-3-(4-chloro­phen­yl)-2-[(3-methyl-1H-indol-1-yl)meth­yl]prop-2-enoate

Selvanayagam, S.; Sridhar, B.; Kathiravan, S.; Raghunathan, R.

doi:10.1107/S2056989015010002

research communications

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 71| Part 6| June 2015| Pages 720-722

doi:10.1107/S2056989015010002

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Crystal structure of methyl (2Z)-3-(4-chlorophenyl)-2-[(3-methyl-1H-indol-1-yl)methyl]prop-2-enoate

S. Selvanayagam,^a ^* B. Sridhar,^b S. Kathiravan ^c and R. Raghunathan ^c

^aDepartment of Physics, Kings College of Engineering, Punalkulam 613 303, India, ^bLaboratory of X-ray Crystallography, Indian Institute of Chemical Technology, Hyderabad 500 067, India, and ^cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: s_selvanayagam@rediffmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 7 May 2015; accepted 23 May 2015; online 30 May 2015)

In the title indole derivative, C₂₀H₁₈ClNO₂, the chlorophenyl ring is almost perpendicular to the indole moiety, making a dihedral angle of 87.6 (1)°. The molecular packing is stabilized by C—H⋯π interactions, which form a C(9) chain motif along [10-1]. In addition, there are weak π–π interactions [centroid–centroid distance 3.851 (1) Å] between the chains, involving inversion-related chlorophenyl rings.

Keywords: crystal structure; indole; methyl methacrylate; C—H⋯π interactions; π–π interactions.

CCDC reference: 1402521

1. Chemical context

Indole derivatives inhibit hepatitis C virus replication through induction of pro-inflammatory cytokines (Lee et al., 2015 ) and these derivatives act as a new anti-hepatitis C virus agents (Andreev et al., 2015 ). These derivatives also act as potential mushroom tyrosinase inhibitors (Ferro et al., 2015 ). Indole derivatives also exhibit anti-proliferative (Parrino et al., 2015 ), anti-inflammatory (Chen et al., 2015 ) and anti-tumor (Ma et al., 2015 ) activities. In view of the many interesting applications of indole derivatives, we synthesized the title compound and report herein on its crystal structure.

2. Structural commentary

The molecular structure of the title compound, (I), is illustrated in Fig. 1. The geometry of the indole ring system (N1/C1–C8) in (I) is comparable with those reported for similar structures, namely 1-vinyl-1H-indole-3-carbaldehyde (II) (Selvanayagam et al., 2008 ) and methyl (2Z)-2-[(2-formyl-3-methyl-1H-indol-1-yl)methyl]-3-(4-methoxyphenyl)-prop-2-enoate (III) (Selvanayagam et al., 2014 ). The superposition of the indole ring system of (I) with the related reported structures, using Qmol (Gans & Shalloway, 2001 ), gives an r.m.s. deviation of 0.025 Å between (I) and (II), and 0.030 Å between (I) and (III); see Fig. 2. The indole ring system is planar with an r.m.s. deviation of 0.017 Å [maximum deviation of 0.028 (2) Å for atom C3], and the methyl atom C9 deviates by 0.050 (2) Å from its mean plane. The chlorine atom, Cl1, deviates by 0.008 (1) Å from the benzene ring (C15–C20) to which it is attached. This ring is almost perpendicular to the indole ring system, making a dihedral angle of 87.59 (6)°. The sum of the angles at atom N1 of the indole ring (360°) is in accordance with sp² hybridization. The widening of the C16—C15—C14 bond angle to 125.2 (1)° is due to the short H⋯H contact (H10B⋯H16 = 2.10 Å). The mean plane of the methyl methacrylate unit [O1/O2/C10–C14; maximum deviation of 0.015 (2) Å for atom O1] is almost planar with the chlrophenyl ring, making a dihedral angle of 18.98 (17)°, but is normal to the indole ring system with a dihedral angle of 89.96 (5)°.

Figure 1
The molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Figure 2
Superposition of (I)

(cyan) with the similar reported structures (II) (yellow; Selvanayagam et al., 2008

) and (III) (green; Selvanayagam et al., 2014

3. Supramolecular features

In the crystal, C—H⋯π interactions link the molecules, forming C(9) chains propagating along [10 $[\overline{1}]$ ]; see Fig. 3 and Table 1. Between the chains there are weak π–π interactions involving inversion-related chlorophenyl rings (C15–C20), stabilizing the molecular packing [centroid-to-centroid distance = 3.851 (1) Å]; see Fig. 4.

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of ring C1–C6.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯Cgⁱ	0.96	2.69	3.581 (2)	154
Symmetry code: (i) $[x-{\script{1\over 2}}, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Figure 3
The molecular packing of the title compound, viewed along the b axis. C—H⋯π interactions (Table 1

) are shown as dashed lines. For clarity, H atoms not involved in these interactions have been omitted.

Figure 4
Molecular packing of the title compound, showing the π–π interactions as dashed lines. For clarity, H atoms not involved in these interactions have been omitted.

4. Synthesis and crystallization

Substituted (Z)-methyl-2-(bromomethyl)-3-phenylacrylate (1 mmol), tetra-butyl-ammonium bromide (0.5 mmol), and 50% NaOH (20 ml) were added to a solution of 3-methyl indole (1 mmol) in benzene (55 ml). The mixture was stirred vigorously at room temperature for 5–6 h. The organic layer was separated, washed with water and dried over MgSO₄. The solvent was evaporated under reduced pressure (yield: 70%). Suitable crystals were obtained by slow evaporation of a solution of the title compound in methanol at room temperature.

5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms were placed in idealized positions and allowed to ride on their parent atoms: C—H = 0.93–0.97 Å, with U_iso(H) = 1.5U_eq(C) for methyl H atoms and 1.2U_eq(C) for other H atoms.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₀H₁₈ClNO₂
M_r	339.80
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	292
a, b, c (Å)	9.5867 (5), 15.9077 (8), 10.8902 (6)
β (°)	94.787 (1)
V (Å³)	1654.99 (15)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.24
Crystal size (mm)	0.20 × 0.18 × 0.16

Data collection
Diffractometer	Bruker SMART APEX CCD area detector
No. of measured, independent and observed [I > 2σ(I)] reflections	19078, 3944, 3313
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.127, 1.02
No. of reflections	3944
No. of parameters	219
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.23
Computer programs: SMART and SAINT (Bruker, 2001 ), SHELXS1997 (Sheldrick, 2008 ), SHELXL2013 (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1402521

Crystal structure: contains datablocks I, global. DOI: 10.1107/S2056989015010002/su5135sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015010002/su5135Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015010002/su5135Isup3.cml

checkCIF report

Chemical context top

Indole derivatives inhibit hepatitis C virus replication through induction of pro-inflammatory cytokines (Lee et al., 2015) and these derivatives act as a new anti-hepatitis C virus agents (Andreev et al., 2015). These derivatives also act as potential mushroom tyrosinase inhibitors (Ferro et al., 2015). Indole derivatives also exhibit anti-proliferative (Parrino et al., 2015), anti-inflammatory (Chen et al., 2015) and anti-tumor (Ma et al., 2015) activities. In view of the many interesting applications of indole derivatives, we synthesized the title compound and report herein on its crystal structure.

Structural commentary top

The molecular structure of the title compound, (I), is illustrated in Fig. 1. The geometry of the indole ring system (N1/C1–C8) in (I) is comparable with those reported for similar structures, namely 1-vinyl-1H-indole-3-carbaldehyde (II) (Selvanayagam et al., 2008) and methyl (2Z)-2-[(2-formyl-3-methyl-1H-indol-1-yl)methyl]-3-(4-methoxyphenyl)-prop-2-enoate (III) (Selvanayagam et al., 2014). The superposition of the indole ring system of (I) with the related reported structures, using Qmol (Gans & Shalloway, 2001), gives an r.m.s. deviation of 0.025 Å between (I) and (II), and 0.030 Å between (I) and (III); see Fig. 2. The indole ring system is planar with an r.m.s. deviation of 0.017 Å [maximum deviation of 0.028 (2) Å for atom C3], and the methyl atom C9 deviates by 0.050 (2) Å from its mean plane. The chlorine atom, Cl1, deviates by 0.008 (1) Å from the benzene ring (C15–C20) to which it is attached. This ring is almost perpendicular to the indole ring system, making a dihedral angle of 87.59 (6)°. The sum of the angles at atom N1 of the indole ring (360°) is in accordance with sp² hybridization. The widening of the C16—C15—C14 bond angle to 125.2 (1)° is due to the short H···H contact (H10B···H16 = 2.10 Å). The mean plane of the methyl methacrylate unit [O1/O2/C10–C14; maximum deviation of 0.015 (2) Å for atom O1] is almost planar with the chlrophenyl ring, making a dihedral angle of 18.98 (17)°, but is normal to the indole ring system with a dihedral angle of 89.96 (5)°.

Supramolecular features top

In the crystal, C—H···π interactions link the molecules, forming C(9) chains propagating along [101]; see Fig. 3 and Table 1. Between the chains there are weak π–π interactions involving inversion-related chlorophenyl rings (C15–C20), stabilizing the molecular packing [centroid-to-centroid distance = 3.851 (1) Å]; see Fig. 4.

Synthesis and crystallization top

Refinement top

Related literature top

For related literature, see: Andreev et al. (2015); Chen et al. (2015); Ferro et al. (2015); Gans & Shalloway (2001); Lee et al. (2015); Ma et al. (2015); Parrino et al. (2015); Selvanayagam et al. (2008, 2014).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS1997 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Superposition of (I) (cyan) with the similar reported structures (II) (yellow; Selvanayagam et al., 2008) and (III) (green; Selvanayagam et al., 2014).
	Fig. 3. The molecular packing of the title compound, viewed along the b axis. C—H···π interactions (Table 1) are shown as dashed lines. For clarity, H atoms not involved in these interactions have been omitted.
	Fig. 4. Molecular packing of the title compound, showing the π–π interactions as dashed lines. For clarity, H atoms not involved in these interactions have been omitted.

Methyl (2Z)-3-(4-chlorophenyl)-2-[(3-methyl-1H-indol-1-yl)methyl]prop-2-enoate top

Crystal data top

C₂₀H₁₈ClNO₂	F(000) = 712
M_r = 339.80	D_x = 1.364 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.5867 (5) Å	Cell parameters from 12437 reflections
b = 15.9077 (8) Å	θ = 2.3–27.7°
c = 10.8902 (6) Å	µ = 0.24 mm⁻¹
β = 94.787 (1)°	T = 292 K
V = 1654.99 (15) Å³	Block, colourless
Z = 4	0.20 × 0.18 × 0.16 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	R_int = 0.026
Radiation source: fine-focus sealed tube	θ_max = 28.0°, θ_min = 2.3°
ω scans	h = −12→12
19078 measured reflections	k = −20→20
3944 independent reflections	l = −14→14
3313 reflections with I > 2σ(I)

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.127	w = 1/[σ²(F_o²) + (0.0722P)² + 0.3404P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.002
3944 reflections	Δρ_max = 0.30 e Å⁻³
219 parameters	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₀H₁₈ClNO₂	V = 1654.99 (15) Å³
M_r = 339.80	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.5867 (5) Å	µ = 0.24 mm⁻¹
b = 15.9077 (8) Å	T = 292 K
c = 10.8902 (6) Å	0.20 × 0.18 × 0.16 mm
β = 94.787 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3313 reflections with I > 2σ(I)
19078 measured reflections	R_int = 0.026
3944 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.02	Δρ_max = 0.30 e Å⁻³
3944 reflections	Δρ_min = −0.23 e Å⁻³
219 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.85221 (5)	1.06092 (3)	0.06559 (4)	0.05976 (16)
O1	0.23237 (16)	0.66473 (11)	−0.05769 (11)	0.0775 (4)
O2	0.21544 (12)	0.62293 (7)	0.13579 (10)	0.0524 (3)
N1	0.32743 (12)	0.78373 (7)	0.30864 (10)	0.0366 (3)
C1	0.32983 (13)	0.78740 (8)	0.43477 (12)	0.0333 (3)
C2	0.40942 (15)	0.74169 (9)	0.52459 (13)	0.0405 (3)
H2	0.4756	0.7027	0.5035	0.049*
C3	0.38621 (16)	0.75652 (10)	0.64588 (13)	0.0472 (4)
H3	0.4365	0.7262	0.7077	0.057*
C4	0.28848 (17)	0.81630 (11)	0.67783 (13)	0.0487 (4)
H4	0.2759	0.8254	0.7605	0.058*
C5	0.21077 (15)	0.86187 (9)	0.58952 (13)	0.0421 (3)
H5	0.1468	0.9018	0.6120	0.051*
C6	0.22927 (13)	0.84726 (8)	0.46513 (12)	0.0341 (3)
C7	0.16518 (14)	0.87978 (9)	0.35139 (13)	0.0384 (3)
C8	0.22748 (14)	0.83989 (9)	0.25968 (13)	0.0390 (3)
H8	0.2059	0.8491	0.1759	0.047*
C9	0.05055 (18)	0.94375 (11)	0.33648 (17)	0.0551 (4)
H9A	0.0297	0.9559	0.2506	0.083*
H9B	0.0800	0.9943	0.3792	0.083*
H9C	−0.0316	0.9221	0.3701	0.083*
C10	0.41548 (15)	0.72823 (9)	0.24128 (12)	0.0391 (3)
H10A	0.4063	0.6711	0.2708	0.047*
H10B	0.5126	0.7449	0.2578	0.047*
C11	0.37749 (15)	0.73022 (9)	0.10415 (12)	0.0395 (3)
C12	0.26941 (16)	0.67031 (10)	0.05008 (14)	0.0457 (3)
C13	0.1091 (2)	0.56359 (11)	0.0915 (2)	0.0622 (5)
H13A	0.0294	0.5934	0.0543	0.093*
H13B	0.0815	0.5306	0.1592	0.093*
H13C	0.1457	0.5272	0.0316	0.093*
C14	0.43561 (15)	0.78067 (10)	0.02431 (13)	0.0427 (3)
H14	0.4052	0.7706	−0.0577	0.051*
C15	0.53784 (15)	0.84850 (9)	0.04181 (13)	0.0418 (3)
C16	0.57356 (18)	0.89031 (11)	0.15350 (14)	0.0499 (4)
H16	0.5315	0.8742	0.2238	0.060*
C17	0.66983 (18)	0.95481 (11)	0.16082 (15)	0.0516 (4)
H17	0.6930	0.9818	0.2355	0.062*
C18	0.73146 (16)	0.97890 (9)	0.05648 (14)	0.0447 (3)
C19	0.69899 (19)	0.93986 (11)	−0.05510 (15)	0.0521 (4)
H19	0.7414	0.9567	−0.1248	0.063*
C20	0.60262 (18)	0.87549 (11)	−0.06176 (14)	0.0495 (4)
H20	0.5800	0.8492	−0.1371	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0659 (3)	0.0532 (3)	0.0606 (3)	−0.00944 (19)	0.0072 (2)	0.00371 (18)
O1	0.0809 (9)	0.1119 (12)	0.0386 (7)	−0.0357 (9)	−0.0008 (6)	−0.0147 (7)
O2	0.0572 (7)	0.0500 (6)	0.0490 (6)	−0.0075 (5)	−0.0016 (5)	−0.0016 (5)
N1	0.0384 (6)	0.0420 (6)	0.0293 (5)	0.0067 (5)	0.0016 (4)	−0.0017 (4)
C1	0.0341 (6)	0.0353 (6)	0.0304 (6)	−0.0008 (5)	0.0024 (5)	−0.0030 (5)
C2	0.0428 (7)	0.0411 (7)	0.0371 (7)	0.0080 (6)	−0.0005 (6)	−0.0006 (6)
C3	0.0524 (9)	0.0538 (9)	0.0341 (7)	0.0067 (7)	−0.0031 (6)	0.0035 (6)
C4	0.0528 (9)	0.0641 (10)	0.0292 (7)	0.0029 (7)	0.0041 (6)	−0.0049 (6)
C5	0.0407 (7)	0.0468 (8)	0.0394 (7)	0.0032 (6)	0.0070 (6)	−0.0069 (6)
C6	0.0328 (6)	0.0344 (6)	0.0351 (7)	−0.0016 (5)	0.0025 (5)	−0.0014 (5)
C7	0.0360 (7)	0.0397 (7)	0.0390 (7)	0.0028 (5)	0.0013 (5)	0.0002 (6)
C8	0.0391 (7)	0.0446 (7)	0.0324 (7)	0.0043 (6)	−0.0010 (5)	0.0031 (5)
C9	0.0504 (9)	0.0552 (10)	0.0591 (10)	0.0181 (7)	0.0013 (7)	0.0038 (8)
C10	0.0403 (7)	0.0446 (7)	0.0321 (7)	0.0069 (6)	0.0016 (5)	−0.0041 (5)
C11	0.0400 (7)	0.0478 (8)	0.0306 (7)	0.0066 (6)	0.0019 (5)	−0.0069 (6)
C12	0.0450 (8)	0.0538 (9)	0.0384 (8)	0.0033 (7)	0.0034 (6)	−0.0098 (6)
C13	0.0606 (11)	0.0505 (9)	0.0739 (12)	−0.0092 (8)	−0.0043 (9)	−0.0039 (8)
C14	0.0433 (8)	0.0540 (8)	0.0305 (7)	0.0056 (6)	0.0007 (6)	−0.0064 (6)
C15	0.0441 (8)	0.0463 (8)	0.0349 (7)	0.0072 (6)	0.0024 (6)	−0.0006 (6)
C16	0.0583 (9)	0.0570 (9)	0.0357 (8)	−0.0043 (7)	0.0108 (7)	−0.0050 (7)
C17	0.0602 (10)	0.0545 (9)	0.0406 (8)	−0.0044 (7)	0.0075 (7)	−0.0088 (7)
C18	0.0456 (8)	0.0406 (8)	0.0476 (8)	0.0049 (6)	0.0024 (6)	0.0041 (6)
C19	0.0626 (10)	0.0563 (10)	0.0384 (8)	−0.0001 (7)	0.0095 (7)	0.0067 (7)
C20	0.0606 (9)	0.0555 (9)	0.0319 (7)	−0.0002 (7)	0.0015 (6)	−0.0003 (6)

Geometric parameters (Å, º) top

Cl1—C18	1.7417 (16)	C9—H9B	0.9600
O1—C12	1.2007 (19)	C9—H9C	0.9600
O2—C12	1.3370 (19)	C10—C11	1.5077 (18)
O2—C13	1.442 (2)	C10—H10A	0.9700
N1—C1	1.3731 (16)	C10—H10B	0.9700
N1—C8	1.3839 (17)	C11—C14	1.338 (2)
N1—C10	1.4607 (17)	C11—C12	1.492 (2)
C1—C2	1.3940 (19)	C13—H13A	0.9600
C1—C6	1.4138 (18)	C13—H13B	0.9600
C2—C3	1.378 (2)	C13—H13C	0.9600
C2—H2	0.9300	C14—C15	1.460 (2)
C3—C4	1.399 (2)	C14—H14	0.9300
C3—H3	0.9300	C15—C20	1.400 (2)
C4—C5	1.373 (2)	C15—C16	1.403 (2)
C4—H4	0.9300	C16—C17	1.378 (2)
C5—C6	1.4001 (19)	C16—H16	0.9300
C5—H5	0.9300	C17—C18	1.378 (2)
C6—C7	1.4327 (19)	C17—H17	0.9300
C7—C8	1.363 (2)	C18—C19	1.377 (2)
C7—C9	1.497 (2)	C19—C20	1.377 (2)
C8—H8	0.9300	C19—H19	0.9300
C9—H9A	0.9600	C20—H20	0.9300

C12—O2—C13	116.06 (13)	N1—C10—H10B	109.1
C1—N1—C8	108.14 (11)	C11—C10—H10B	109.1
C1—N1—C10	124.46 (11)	H10A—C10—H10B	107.8
C8—N1—C10	127.39 (11)	C14—C11—C12	116.07 (13)
N1—C1—C2	129.96 (12)	C14—C11—C10	125.23 (13)
N1—C1—C6	107.92 (11)	C12—C11—C10	118.67 (13)
C2—C1—C6	122.09 (12)	O1—C12—O2	122.72 (15)
C3—C2—C1	117.42 (13)	O1—C12—C11	124.88 (16)
C3—C2—H2	121.3	O2—C12—C11	112.39 (12)
C1—C2—H2	121.3	O2—C13—H13A	109.5
C2—C3—C4	121.32 (14)	O2—C13—H13B	109.5
C2—C3—H3	119.3	H13A—C13—H13B	109.5
C4—C3—H3	119.3	O2—C13—H13C	109.5
C5—C4—C3	121.33 (13)	H13A—C13—H13C	109.5
C5—C4—H4	119.3	H13B—C13—H13C	109.5
C3—C4—H4	119.3	C11—C14—C15	132.06 (13)
C4—C5—C6	119.00 (13)	C11—C14—H14	114.0
C4—C5—H5	120.5	C15—C14—H14	114.0
C6—C5—H5	120.5	C20—C15—C16	117.42 (15)
C5—C6—C1	118.81 (12)	C20—C15—C14	117.37 (13)
C5—C6—C7	134.17 (13)	C16—C15—C14	125.19 (14)
C1—C6—C7	107.01 (11)	C17—C16—C15	121.12 (15)
C8—C7—C6	106.44 (12)	C17—C16—H16	119.4
C8—C7—C9	126.87 (14)	C15—C16—H16	119.4
C6—C7—C9	126.68 (13)	C18—C17—C16	119.37 (15)
C7—C8—N1	110.49 (12)	C18—C17—H17	120.3
C7—C8—H8	124.8	C16—C17—H17	120.3
N1—C8—H8	124.8	C19—C18—C17	121.42 (15)
C7—C9—H9A	109.5	C19—C18—Cl1	119.23 (12)
C7—C9—H9B	109.5	C17—C18—Cl1	119.34 (12)
H9A—C9—H9B	109.5	C18—C19—C20	118.89 (15)
C7—C9—H9C	109.5	C18—C19—H19	120.6
H9A—C9—H9C	109.5	C20—C19—H19	120.6
H9B—C9—H9C	109.5	C19—C20—C15	121.77 (15)
N1—C10—C11	112.50 (11)	C19—C20—H20	119.1
N1—C10—H10A	109.1	C15—C20—H20	119.1
C11—C10—H10A	109.1

C8—N1—C1—C2	178.13 (14)	C8—N1—C10—C11	−6.0 (2)
C10—N1—C1—C2	−1.0 (2)	N1—C10—C11—C14	92.47 (17)
C8—N1—C1—C6	−0.08 (15)	N1—C10—C11—C12	−89.24 (16)
C10—N1—C1—C6	−179.21 (12)	C13—O2—C12—O1	0.2 (2)
N1—C1—C2—C3	−177.65 (14)	C13—O2—C12—C11	179.53 (13)
C6—C1—C2—C3	0.3 (2)	C14—C11—C12—O1	0.0 (2)
C1—C2—C3—C4	−1.2 (2)	C10—C11—C12—O1	−178.46 (16)
C2—C3—C4—C5	0.7 (3)	C14—C11—C12—O2	−179.30 (13)
C3—C4—C5—C6	0.7 (2)	C10—C11—C12—O2	2.25 (19)
C4—C5—C6—C1	−1.5 (2)	C12—C11—C14—C15	176.82 (14)
C4—C5—C6—C7	177.51 (15)	C10—C11—C14—C15	−4.9 (3)
N1—C1—C6—C5	179.37 (12)	C11—C14—C15—C20	164.77 (16)
C2—C1—C6—C5	1.0 (2)	C11—C14—C15—C16	−17.0 (3)
N1—C1—C6—C7	0.14 (15)	C20—C15—C16—C17	−0.7 (2)
C2—C1—C6—C7	−178.25 (13)	C14—C15—C16—C17	−178.87 (15)
C5—C6—C7—C8	−179.20 (15)	C15—C16—C17—C18	0.3 (3)
C1—C6—C7—C8	−0.14 (15)	C16—C17—C18—C19	0.0 (3)
C5—C6—C7—C9	−0.3 (3)	C16—C17—C18—Cl1	179.55 (13)
C1—C6—C7—C9	178.81 (15)	C17—C18—C19—C20	0.1 (3)
C6—C7—C8—N1	0.09 (16)	Cl1—C18—C19—C20	−179.51 (13)
C9—C7—C8—N1	−178.86 (14)	C18—C19—C20—C15	−0.4 (3)
C1—N1—C8—C7	0.00 (16)	C16—C15—C20—C19	0.7 (2)
C10—N1—C8—C7	179.09 (13)	C14—C15—C20—C19	179.06 (15)
C1—N1—C10—C11	172.92 (13)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of ring C1–C6.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···Cgⁱ	0.96	2.69	3.581 (2)	154

Symmetry code: (i) x−1/2, −y−1/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of ring C1–C6.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···Cgⁱ	0.96	2.69	3.581 (2)	154

Symmetry code: (i) x−1/2, −y−1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈ClNO₂
M_r	339.80
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	292
a, b, c (Å)	9.5867 (5), 15.9077 (8), 10.8902 (6)
β (°)	94.787 (1)
V (Å³)	1654.99 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.20 × 0.18 × 0.16

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	19078, 3944, 3313
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.127, 1.02
No. of reflections	3944
No. of parameters	219
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.23

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS1997 (Sheldrick, 2008), SHELXL2013 (Sheldrick, 2015), ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009), SHELXL2013 (Sheldrick, 2008) and PLATON (Spek, 2009).

Acknowledgements

SS thanks the Principal and Management of Kings College of Engineering, Punalkulam, for their support and encouragement.

References

Andreev, I. A., Manvar, D., Barreca, M. L., Belov, D. S., Basu, A., Sweeney, N. L., Ratmanova, N. K., Lukyanenko, E. R., Manfroni, G., Cecchetti, V., Frick, D. N., Altieri, A., Kaushik-Basu, N. & Kurkin, A. V. (2015). Eur. J. Med. Chem. 96, 250–258. CrossRef CAS PubMed Google Scholar
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Volume 71| Part 6| June 2015| Pages 720-722

doi:10.1107/S2056989015010002

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research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of methyl (2Z)-3-(4-chloro­phen­yl)-2-[(3-methyl-1H-indol-1-yl)meth­yl]prop-2-enoate

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Synthesis and crystallization

5. Refinement

Supporting information

Acknowledgements

References

research communications

Crystal structure of methyl (2Z)-3-(4-chlorophenyl)-2-[(3-methyl-1H-indol-1-yl)methyl]prop-2-enoate

3. Supramolecular features