5-Benzoyl-2-(1H-indol-3-yl)-4-(naphthalen-2-yl)-1H-pyrrole-3-carbo­nitrile

Vimala, G.; Raja, J.K.; Perumal, P.T.; SubbiahPandi, A.

doi:10.1107/S2414314616005265

organic compounds

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ISSN: 2414-3146

Volume 1| Part 4| April 2016| x160526

doi:10.1107/S2414314616005265

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5-Benzoyl-2-(1H-indol-3-yl)-4-(naphthalen-2-yl)-1H-pyrrole-3-carbonitrile

G. Vimala,^a J. Kamal Raja,^b P. T. Perumal ^b and A. SubbiahPandi ^a ^*

^aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and ^bOrganic Chemistry, CSIR Central Leather Research Institute, Adyar, Chennai 600 020, India
^*Correspondence e-mail: aspandian59@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 14 March 2016; accepted 29 March 2016; online 12 April 2016)

In the title compound, C₃₀H₁₉N₃O, the indole and the naphthalene ring systems are inclined to the central pyrrole ring (r.m.s. deviation = 0.012 Å) by 29.09 (9) and 49.92 (9)°, respectively. The naphthalene ring system and the indole ring are inclined to one another by 73.57 (6) and by 42.58 (10) and 74.12 (10)°, respectively, to the benzoyl ring. In the crystal, molecules are linked by pairs of N_p—H⋯O (p = pyrrole) hydrogen bonds, forming inversion dimers with R²₂(10) loops. These dimers are linked via pairs of N_i—H⋯N_c (i = indole and c = carbonitrile) hydrogen bonds, enclosing R²₂(16) loops, which leads to the formation of chains propagating in [101]. The chains are linked by C—H⋯π interactions, forming slabs lying parallel to (10-1).

Keywords: crystal structure; indole; indole alkaloids; naphthalene; 3-carbonitrile-pyrrole; inversion dimers; hydrogen bonding.

CCDC reference: 1471048

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Chemical scheme

Structure description

Indole derivatives exhibit antibacterial, antifungal (Singh et al. 2000 ), antitumor (Andreani et al., 2001 ), antihepatitis B virus (Chai et al., 2006 ) and anti-inflammatory (Rodriguez et al., 1985 ) activities. Some of the indole alkaloids extracted from plants possess interesting cytotoxic and antiparasitic properties (Quetin-Leclercq, 1994 ). They are also used as bioactive drugs (Stevenson et al., 2000 ) and have also been shown to display high aldose reductase inhibitory (Rajeswaran et al., 1999 ) and antimicrobial activities (Amal Raj et al., 2003 ). As part of our studies of this family of compounds, we synthesized the title indole derivative and report herein on its crystal structure.

The molecular structure of the title compound is illustrated in Fig. 1. The five-membered central pyrrole ring (N2/C2–C5; r.m.s. deviation = 0.012 Å) makes dihedral angles of 29.09 (9) and 45.92 (9)° with the indole ring (N3/C23–C30) and the naphthalene ring system (C6–C15), respectively. The naphthalene ring system and the benzoyl ring (C17–C22) are inclined to the indole ring by 73.57 (6) and 74.12 (10)°, respectively. The bond lengths and bond angles are similar to those for reported similar structures (Vimala et al., 2015 ; Inglebert et al., 2013 ).

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

In the crystal, molecules are linked by pairs of N_p—H⋯O (p = pyrrole) hydrogen bonds, forming inversion dimers with $[R_{2}^{2}]$ (10) loops (Table 1 and Fig. 2). These dimers are linked via pairs of N_i—H⋯N_c (i = indole and c = carbonitrile) hydrogen bonds, enclosing $[R_{2}^{2}]$ (16) loops, which leads to the formation of chains propagating in [101]; see Table 1 and Fig. 2. The chains are linked by C—H⋯π interactions (Table 1), forming slabs lying parallel to (10 $[\overline{1}]$ ).

Table 1
Hydrogen-bond geometry (Å, °)

Cg3, Cg4 and Cg6 are the centroids of rings C6–C9/C14/C15, C9–C14 and C25–C30, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1ⁱ	0.86	2.15	2.875 (2)	141
N3—H3⋯N1ⁱⁱ	0.86	2.27	3.023 (3)	147
C22—H22⋯Cg6ⁱ	0.93	2.58	3.456 (2)	158
C26—H26⋯Cg4ⁱⁱⁱ	0.93	2.98	3.784 (2)	146
C27—H27⋯Cg3ⁱⁱⁱ	0.93	2.74	3.555 (2)	147
Symmetry codes: (i) -x, -y, -z; (ii) -x+1, -y, -z+1; (iii) x, y+1, z.

Figure 2
The crystal packing of the title compound, viewed along the a axis. The hydrogen bonds are shown as dashed lines (see Table 1

), and C-bound H atoms have been omitted for clarity.

Synthesis and crystallization

To a stirred mixture of 2-naphthaldehyde 1 (1.0 mmol), 3-cyanoacetylindole 2 (1.0 mmol) and phenacylazide 3 (1.0 mmol) in water (3 ml), piperidine (0.25 mmol) was added at 353 K. The turbid solution slowly turned into a clear solution, followed by the formation of a solid after 2 h. After completion of the reaction, as indicated by TLC, the solid was filtered and washed with a petroleum ether–EtOAc mixture (1:1 ratio, v/v, 5 ml) to give the pure compound (as confirmed by TLC, NMR and mass spectroscopy). The compound was recrystallized from ethanol solution by slow evaporation, giving yellow block-like crystals of the title compound (yield 86%).

Refinement

Crystal data, data collection and structure refinement details for the title compound are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₃₀H₁₉N₃O
M_r	437.48
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	293
a, b, c (Å)	10.2688 (4), 10.5322 (4), 11.2934 (4)
α, β, γ (°)	111.720 (2), 93.883 (2), 91.653 (3)
V (Å³)	1130.18 (7)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004 )
T_min, T_max	0.984, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	25456, 3992, 2997
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.129, 0.74
No. of reflections	3950
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.20
Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008 ), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1471048

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2414314616005265/su4022sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616005265/su4022Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616005265/su4022Isup3.cml

checkCIF report

Experimental top

To a stirred mixture of 2-naphthaldehyde 1 (1.0 mmol), 3-cyanoacetylindole 2 (1.0 mmol) and phenacylazide 3 (1.0 mmol) in water (3 ml), piperidine (0.25 mmol) was added at 353 K. The turbid solution slowly turned into a clear solution, followed by the formation of a solid after 2 h. After completion of the reaction, as indicated by TLC, the solid was filtered and washed with a petroleum ether–EtOAc mixture (1:1 ratio, v/v, 5 ml) to give a pure compound. This pure compound was recrystallized from ethanol by slow evaporation giving yellow block-like crystals of the title compound (yield 86%).

Structure description top

Indole derivatives exhibit antibacterial, antifungal (Singh et al. 2000), antitumor (Andreani et al., 2001), antihepatitis B virus (Chai et al., 2006) and anti-inflammatory (Rodriguez et al., 1985) activities. Some of the indole alkaloids extracted from plants possess interesting cytotoxic and antiparasitic properties (Quetin-Leclercq, 1994). They are also used as bioactive drugs (Stevenson et al., 2000) and have also been shown to display high aldose reductase inhibitory (Rajeswaran et al., 1999) and antimicrobial activities (Amal Raj et al., 2003). In view of the importance of such compounds, we synthesized the title indole derivative and report herein on its crystal structure.

In the crystal, molecules are linked by pairs of N_p—H···O (p = pyrrole) hydrogen bonds, forming inversion dimers with R²₂(10) loops (Table 1 and Fig. 2). These dimers are linked via pairs of N_i—H···N_c (i = indole and c = carbonitrile) hydrogen bonds, enclosing R²₂(16) loops, which leads to the formation of chains propagating in [101]; see Table 1 and Fig. 2. The chains are linked by C—H···π interactions (Table 1), forming slabs lying parallel to (101).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at 30% probability level.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis. The hydrogen bonds are shown as dashed lines (see Table 1), and C-bound H atoms have been omitted for clarity.

5-Benzoyl-2-(1H-indol-3-yl)-4-(naphthalen-2-yl)-1H-pyrrole-3-carbonitrile top

Crystal data top

C₃₀H₁₉N₃O	Z = 2
M_r = 437.48	F(000) = 456
Triclinic, P1	D_x = 1.285 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.2688 (4) Å	Cell parameters from 2997 reflections
b = 10.5322 (4) Å	θ = 2.0–25.0°
c = 11.2934 (4) Å	µ = 0.08 mm⁻¹
α = 111.720 (2)°	T = 293 K
β = 93.883 (2)°	Block, yellow
γ = 91.653 (3)°	0.30 × 0.25 × 0.20 mm
V = 1130.18 (7) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	3992 independent reflections
Radiation source: fine-focus sealed tube	2997 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω and φ scan	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −12→12
T_min = 0.984, T_max = 0.987	k = −12→12
25456 measured reflections	l = −13→13

Refinement top

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 0.74	w = 1/[σ²(F_o²) + (0.0737P)² + 1.3759P] where P = (F_o² + 2F_c²)/3
3950 reflections	(Δ/σ)_max < 0.001
307 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₃₀H₁₉N₃O	γ = 91.653 (3)°
M_r = 437.48	V = 1130.18 (7) Å³
Triclinic, P1	Z = 2
a = 10.2688 (4) Å	Mo Kα radiation
b = 10.5322 (4) Å	µ = 0.08 mm⁻¹
c = 11.2934 (4) Å	T = 293 K
α = 111.720 (2)°	0.30 × 0.25 × 0.20 mm
β = 93.883 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3992 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2997 reflections with I > 2σ(I)
T_min = 0.984, T_max = 0.987	R_int = 0.030
25456 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 0.74	Δρ_max = 0.15 e Å⁻³
3950 reflections	Δρ_min = −0.19 e Å⁻³
307 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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) 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
N2	0.06088 (15)	−0.00372 (16)	0.19168 (15)	0.0361 (4)
H2	0.0550	0.0483	0.1484	0.043*
C6	−0.04251 (18)	−0.29361 (19)	0.27603 (18)	0.0344 (4)
C16	−0.14783 (18)	−0.12464 (19)	0.09442 (17)	0.0341 (4)
O1	−0.14205 (14)	−0.08637 (15)	0.00453 (13)	0.0473 (4)
C15	−0.08017 (18)	−0.40765 (19)	0.17018 (18)	0.0355 (4)
H15	−0.0728	−0.4049	0.0895	0.043*
C3	0.16176 (18)	0.00371 (19)	0.27732 (17)	0.0343 (4)
C4	−0.03160 (18)	−0.10523 (19)	0.18232 (17)	0.0340 (4)
C17	−0.27269 (18)	−0.18422 (19)	0.11539 (18)	0.0360 (4)
C14	−0.12994 (18)	−0.52944 (19)	0.1799 (2)	0.0383 (5)
C5	0.01315 (18)	−0.16945 (19)	0.26318 (17)	0.0338 (4)
C24	0.27135 (18)	0.10241 (19)	0.30757 (18)	0.0363 (4)
C7	−0.0546 (2)	−0.2977 (2)	0.39845 (19)	0.0446 (5)
H7	−0.0293	−0.2208	0.4712	0.054*
C2	0.13406 (18)	−0.09886 (19)	0.32411 (18)	0.0360 (4)
C25	0.27433 (18)	0.23655 (19)	0.30202 (17)	0.0335 (4)
N3	0.47408 (17)	0.19722 (19)	0.36922 (18)	0.0511 (5)
H3	0.5558	0.2072	0.3951	0.061*
C1	0.2157 (2)	−0.1277 (2)	0.4167 (2)	0.0413 (5)
C26	0.18131 (19)	0.3171 (2)	0.27229 (19)	0.0392 (5)
H26	0.0953	0.2831	0.2456	0.047*
C9	−0.1415 (2)	−0.5319 (2)	0.3034 (2)	0.0435 (5)
C18	−0.3052 (2)	−0.1726 (2)	0.2361 (2)	0.0437 (5)
H18	−0.2481	−0.1261	0.3077	0.052*
N1	0.2814 (2)	−0.1508 (2)	0.4910 (2)	0.0592 (5)
C27	0.2193 (2)	0.4470 (2)	0.2832 (2)	0.0476 (5)
H27	0.1575	0.5017	0.2654	0.057*
C8	−0.1029 (2)	−0.4134 (2)	0.4105 (2)	0.0504 (6)
H8	−0.1106	−0.4141	0.4919	0.061*
C29	0.4423 (2)	0.4229 (2)	0.3486 (2)	0.0473 (5)
H29	0.5287	0.4571	0.3718	0.057*
C10	−0.1894 (2)	−0.6545 (2)	0.3141 (3)	0.0583 (6)
H10	−0.1973	−0.6572	0.3947	0.070*
C28	0.3479 (2)	0.4990 (2)	0.3203 (2)	0.0508 (6)
H28	0.3703	0.5874	0.3260	0.061*
C30	0.40339 (19)	0.2926 (2)	0.34107 (18)	0.0393 (5)
C13	−0.1667 (2)	−0.6492 (2)	0.0723 (2)	0.0520 (6)
H13	−0.1600	−0.6491	−0.0094	0.062*
C23	0.3952 (2)	0.0853 (2)	0.3500 (2)	0.0489 (5)
H23	0.4213	0.0076	0.3636	0.059*
C22	−0.3603 (2)	−0.2515 (2)	0.0105 (2)	0.0505 (6)
H22	−0.3404	−0.2572	−0.0704	0.061*
C12	−0.2121 (2)	−0.7655 (2)	0.0868 (3)	0.0656 (7)
H12	−0.2356	−0.8440	0.0150	0.079*
C11	−0.2235 (3)	−0.7672 (3)	0.2089 (3)	0.0685 (8)
H11	−0.2549	−0.8468	0.2176	0.082*
C20	−0.5076 (3)	−0.2994 (3)	0.1439 (3)	0.0733 (8)
H20	−0.5864	−0.3391	0.1534	0.088*
C21	−0.4763 (2)	−0.3098 (3)	0.0249 (3)	0.0678 (7)
H21	−0.5339	−0.3565	−0.0463	0.081*
C19	−0.4231 (2)	−0.2306 (3)	0.2493 (2)	0.0604 (7)
H19	−0.4451	−0.2230	0.3300	0.072*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N2	0.0379 (9)	0.0380 (9)	0.0386 (9)	−0.0036 (7)	−0.0047 (7)	0.0233 (7)
C6	0.0350 (10)	0.0348 (10)	0.0377 (10)	0.0054 (8)	0.0028 (8)	0.0185 (8)
C16	0.0392 (10)	0.0321 (10)	0.0327 (10)	−0.0004 (8)	−0.0024 (8)	0.0150 (8)
O1	0.0489 (8)	0.0579 (9)	0.0435 (8)	−0.0119 (7)	−0.0089 (7)	0.0317 (7)
C15	0.0354 (10)	0.0391 (10)	0.0365 (10)	0.0043 (8)	0.0038 (8)	0.0189 (9)
C3	0.0341 (10)	0.0356 (10)	0.0354 (10)	0.0033 (8)	−0.0013 (8)	0.0164 (8)
C4	0.0376 (10)	0.0339 (10)	0.0330 (10)	−0.0030 (8)	−0.0012 (8)	0.0164 (8)
C17	0.0352 (10)	0.0365 (10)	0.0388 (11)	0.0021 (8)	−0.0003 (8)	0.0174 (8)
C14	0.0317 (10)	0.0359 (10)	0.0496 (12)	0.0060 (8)	0.0061 (8)	0.0177 (9)
C5	0.0380 (10)	0.0332 (10)	0.0319 (10)	0.0038 (8)	0.0008 (8)	0.0143 (8)
C24	0.0360 (10)	0.0366 (10)	0.0374 (10)	−0.0008 (8)	−0.0046 (8)	0.0167 (8)
C7	0.0588 (13)	0.0416 (11)	0.0358 (11)	0.0025 (10)	0.0037 (9)	0.0174 (9)
C2	0.0386 (10)	0.0357 (10)	0.0368 (10)	0.0033 (8)	−0.0032 (8)	0.0180 (8)
C25	0.0346 (10)	0.0365 (10)	0.0291 (9)	0.0001 (8)	0.0005 (8)	0.0123 (8)
N3	0.0321 (9)	0.0598 (12)	0.0661 (12)	−0.0051 (8)	−0.0136 (8)	0.0327 (10)
C1	0.0444 (11)	0.0356 (11)	0.0456 (12)	−0.0014 (9)	−0.0068 (9)	0.0193 (9)
C26	0.0372 (10)	0.0402 (11)	0.0412 (11)	0.0040 (8)	0.0034 (8)	0.0163 (9)
C9	0.0405 (11)	0.0425 (11)	0.0578 (13)	0.0087 (9)	0.0132 (10)	0.0286 (10)
C18	0.0432 (11)	0.0498 (12)	0.0406 (11)	0.0073 (9)	0.0041 (9)	0.0193 (10)
N1	0.0602 (12)	0.0602 (12)	0.0643 (13)	−0.0040 (10)	−0.0216 (10)	0.0367 (11)
C27	0.0523 (13)	0.0419 (12)	0.0541 (13)	0.0113 (10)	0.0090 (10)	0.0227 (10)
C8	0.0635 (14)	0.0553 (14)	0.0441 (12)	0.0081 (11)	0.0148 (10)	0.0300 (11)
C29	0.0466 (12)	0.0480 (12)	0.0432 (12)	−0.0134 (10)	−0.0038 (9)	0.0148 (10)
C10	0.0570 (14)	0.0509 (14)	0.0846 (18)	0.0086 (11)	0.0245 (13)	0.0420 (14)
C28	0.0644 (15)	0.0377 (11)	0.0506 (13)	−0.0038 (10)	0.0070 (11)	0.0169 (10)
C30	0.0367 (10)	0.0457 (11)	0.0343 (10)	−0.0027 (9)	−0.0044 (8)	0.0150 (9)
C13	0.0484 (13)	0.0434 (12)	0.0594 (14)	0.0002 (10)	0.0088 (11)	0.0131 (11)
C23	0.0427 (12)	0.0496 (13)	0.0610 (14)	−0.0005 (10)	−0.0097 (10)	0.0309 (11)
C22	0.0424 (12)	0.0665 (15)	0.0430 (12)	−0.0084 (10)	−0.0010 (9)	0.0225 (11)
C12	0.0572 (15)	0.0372 (13)	0.093 (2)	−0.0017 (10)	0.0140 (14)	0.0127 (13)
C11	0.0607 (16)	0.0431 (14)	0.111 (2)	0.0036 (11)	0.0278 (15)	0.0360 (15)
C20	0.0465 (14)	0.101 (2)	0.081 (2)	−0.0155 (14)	0.0082 (13)	0.0447 (17)
C21	0.0483 (14)	0.090 (2)	0.0606 (16)	−0.0231 (13)	−0.0077 (12)	0.0264 (14)
C19	0.0531 (14)	0.0819 (18)	0.0583 (15)	0.0076 (13)	0.0189 (12)	0.0376 (14)

Geometric parameters (Å, º) top

N2—C3	1.348 (2)	C1—N1	1.141 (3)
N2—C4	1.378 (2)	C26—C27	1.370 (3)
N2—H2	0.8600	C26—H26	0.9300
C6—C15	1.367 (3)	C9—C8	1.402 (3)
C6—C7	1.413 (3)	C9—C10	1.417 (3)
C6—C5	1.472 (3)	C18—C19	1.381 (3)
C16—O1	1.227 (2)	C18—H18	0.9300
C16—C4	1.458 (3)	C27—C28	1.391 (3)
C16—C17	1.483 (3)	C27—H27	0.9300
C15—C14	1.412 (3)	C8—H8	0.9300
C15—H15	0.9300	C29—C28	1.370 (3)
C3—C2	1.397 (3)	C29—C30	1.389 (3)
C3—C24	1.443 (3)	C29—H29	0.9300
C4—C5	1.386 (3)	C10—C11	1.349 (4)
C17—C22	1.383 (3)	C10—H10	0.9300
C17—C18	1.388 (3)	C28—H28	0.9300
C14—C13	1.409 (3)	C13—C12	1.368 (3)
C14—C9	1.418 (3)	C13—H13	0.9300
C5—C2	1.421 (3)	C23—H23	0.9300
C24—C23	1.368 (3)	C22—C21	1.372 (3)
C24—C25	1.437 (3)	C22—H22	0.9300
C7—C8	1.360 (3)	C12—C11	1.398 (4)
C7—H7	0.9300	C12—H12	0.9300
C2—C1	1.421 (3)	C11—H11	0.9300
C25—C26	1.400 (3)	C20—C21	1.369 (4)
C25—C30	1.408 (3)	C20—C19	1.371 (4)
N3—C23	1.351 (3)	C20—H20	0.9300
N3—C30	1.372 (3)	C21—H21	0.9300
N3—H3	0.8600	C19—H19	0.9300

C3—N2—C4	111.47 (15)	C8—C9—C10	122.5 (2)
C3—N2—H2	124.3	C14—C9—C10	118.9 (2)
C4—N2—H2	124.3	C19—C18—C17	119.6 (2)
C15—C6—C7	118.99 (18)	C19—C18—H18	120.2
C15—C6—C5	120.71 (17)	C17—C18—H18	120.2
C7—C6—C5	120.28 (17)	C26—C27—C28	121.7 (2)
O1—C16—C4	118.79 (17)	C26—C27—H27	119.2
O1—C16—C17	120.14 (16)	C28—C27—H27	119.2
C4—C16—C17	121.03 (16)	C7—C8—C9	121.70 (19)
C6—C15—C14	121.82 (18)	C7—C8—H8	119.2
C6—C15—H15	119.1	C9—C8—H8	119.2
C14—C15—H15	119.1	C28—C29—C30	117.08 (19)
N2—C3—C2	105.95 (16)	C28—C29—H29	121.5
N2—C3—C24	123.18 (17)	C30—C29—H29	121.5
C2—C3—C24	130.88 (17)	C11—C10—C9	120.9 (2)
N2—C4—C5	107.75 (16)	C11—C10—H10	119.6
N2—C4—C16	117.92 (16)	C9—C10—H10	119.6
C5—C4—C16	134.31 (17)	C29—C28—C27	121.4 (2)
C22—C17—C18	119.26 (19)	C29—C28—H28	119.3
C22—C17—C16	118.33 (18)	C27—C28—H28	119.3
C18—C17—C16	122.40 (17)	N3—C30—C29	129.86 (19)
C13—C14—C15	122.87 (19)	N3—C30—C25	107.47 (17)
C13—C14—C9	118.61 (19)	C29—C30—C25	122.67 (19)
C15—C14—C9	118.52 (18)	C12—C13—C14	120.7 (2)
C4—C5—C2	105.71 (16)	C12—C13—H13	119.7
C4—C5—C6	128.48 (17)	C14—C13—H13	119.7
C2—C5—C6	125.52 (16)	N3—C23—C24	110.37 (18)
C23—C24—C25	106.17 (17)	N3—C23—H23	124.8
C23—C24—C3	125.53 (18)	C24—C23—H23	124.8
C25—C24—C3	128.29 (17)	C21—C22—C17	120.4 (2)
C8—C7—C6	120.37 (19)	C21—C22—H22	119.8
C8—C7—H7	119.8	C17—C22—H22	119.8
C6—C7—H7	119.8	C13—C12—C11	120.4 (2)
C3—C2—C1	124.81 (17)	C13—C12—H12	119.8
C3—C2—C5	109.08 (16)	C11—C12—H12	119.8
C1—C2—C5	126.10 (17)	C10—C11—C12	120.5 (2)
C26—C25—C30	118.37 (18)	C10—C11—H11	119.7
C26—C25—C24	134.94 (18)	C12—C11—H11	119.7
C30—C25—C24	106.66 (16)	C21—C20—C19	120.1 (2)
C23—N3—C30	109.33 (17)	C21—C20—H20	119.9
C23—N3—H3	125.3	C19—C20—H20	119.9
C30—N3—H3	125.3	C20—C21—C22	120.2 (2)
N1—C1—C2	179.9 (3)	C20—C21—H21	119.9
C27—C26—C25	118.76 (19)	C22—C21—H21	119.9
C27—C26—H26	120.6	C20—C19—C18	120.4 (2)
C25—C26—H26	120.6	C20—C19—H19	119.8
C8—C9—C14	118.60 (18)	C18—C19—H19	119.8

C7—C6—C15—C14	−0.4 (3)	C3—C24—C25—C30	179.78 (19)
C5—C6—C15—C14	177.95 (17)	C3—C2—C1—N1	−38 (100)
C4—N2—C3—C2	0.8 (2)	C5—C2—C1—N1	141 (100)
C4—N2—C3—C24	−179.00 (17)	C30—C25—C26—C27	−0.4 (3)
C3—N2—C4—C5	−1.7 (2)	C24—C25—C26—C27	176.9 (2)
C3—N2—C4—C16	179.21 (17)	C13—C14—C9—C8	178.97 (19)
O1—C16—C4—N2	23.7 (3)	C15—C14—C9—C8	−0.1 (3)
C17—C16—C4—N2	−153.80 (17)	C13—C14—C9—C10	0.1 (3)
O1—C16—C4—C5	−155.0 (2)	C15—C14—C9—C10	−178.97 (18)
C17—C16—C4—C5	27.5 (3)	C22—C17—C18—C19	1.3 (3)
O1—C16—C17—C22	28.7 (3)	C16—C17—C18—C19	−179.9 (2)
C4—C16—C17—C22	−153.85 (19)	C25—C26—C27—C28	1.4 (3)
O1—C16—C17—C18	−150.2 (2)	C6—C7—C8—C9	0.4 (3)
C4—C16—C17—C18	27.3 (3)	C14—C9—C8—C7	−0.3 (3)
C6—C15—C14—C13	−178.58 (19)	C10—C9—C8—C7	178.5 (2)
C6—C15—C14—C9	0.4 (3)	C8—C9—C10—C11	−178.9 (2)
N2—C4—C5—C2	1.9 (2)	C14—C9—C10—C11	0.0 (3)
C16—C4—C5—C2	−179.3 (2)	C30—C29—C28—C27	−1.3 (3)
N2—C4—C5—C6	−172.21 (18)	C26—C27—C28—C29	−0.5 (3)
C16—C4—C5—C6	6.6 (4)	C23—N3—C30—C29	178.8 (2)
C15—C6—C5—C4	46.2 (3)	C23—N3—C30—C25	−0.2 (2)
C7—C6—C5—C4	−135.5 (2)	C28—C29—C30—N3	−176.7 (2)
C15—C6—C5—C2	−126.8 (2)	C28—C29—C30—C25	2.2 (3)
C7—C6—C5—C2	51.5 (3)	C26—C25—C30—N3	177.73 (18)
N2—C3—C24—C23	−152.6 (2)	C24—C25—C30—N3	−0.3 (2)
C2—C3—C24—C23	27.7 (3)	C26—C25—C30—C29	−1.4 (3)
N2—C3—C24—C25	28.5 (3)	C24—C25—C30—C29	−179.39 (19)
C2—C3—C24—C25	−151.3 (2)	C15—C14—C13—C12	178.8 (2)
C15—C6—C7—C8	0.0 (3)	C9—C14—C13—C12	−0.3 (3)
C5—C6—C7—C8	−178.36 (19)	C30—N3—C23—C24	0.7 (3)
N2—C3—C2—C1	179.65 (19)	C25—C24—C23—N3	−0.8 (2)
C24—C3—C2—C1	−0.5 (3)	C3—C24—C23—N3	−179.97 (19)
N2—C3—C2—C5	0.4 (2)	C18—C17—C22—C21	−2.0 (4)
C24—C3—C2—C5	−179.81 (19)	C16—C17—C22—C21	179.1 (2)
C4—C5—C2—C3	−1.4 (2)	C14—C13—C12—C11	0.4 (4)
C6—C5—C2—C3	172.89 (18)	C9—C10—C11—C12	0.1 (4)
C4—C5—C2—C1	179.3 (2)	C13—C12—C11—C10	−0.3 (4)
C6—C5—C2—C1	−6.4 (3)	C19—C20—C21—C22	0.0 (5)
C23—C24—C25—C26	−176.9 (2)	C17—C22—C21—C20	1.4 (4)
C3—C24—C25—C26	2.3 (4)	C21—C20—C19—C18	−0.7 (4)
C23—C24—C25—C30	0.7 (2)	C17—C18—C19—C20	0.0 (4)

Hydrogen-bond geometry (Å, º) top

Cg3, Cg4 and Cg6 are the centroids of rings C6–C9/C14/C15, C9–C14 and C25–C30, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.86	2.15	2.875 (2)	141
N3—H3···N1ⁱⁱ	0.86	2.27	3.023 (3)	147
C22—H22···Cg6ⁱ	0.93	2.58	3.456 (2)	158
C26—H26···Cg4ⁱⁱⁱ	0.93	2.98	3.784 (2)	146
C27—H27···Cg3ⁱⁱⁱ	0.93	2.74	3.555 (2)	147

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

Hydrogen-bond geometry (Å, º) top

Cg3, Cg4 and Cg6 are the centroids of rings C6–C9/C14/C15, C9–C14 and C25–C30, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.86	2.15	2.875 (2)	141
N3—H3···N1ⁱⁱ	0.86	2.27	3.023 (3)	147
C22—H22···Cg6ⁱ	0.93	2.58	3.456 (2)	158
C26—H26···Cg4ⁱⁱⁱ	0.93	2.98	3.784 (2)	146
C27—H27···Cg3ⁱⁱⁱ	0.93	2.74	3.555 (2)	147

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

Experimental details

Crystal data
Chemical formula	C₃₀H₁₉N₃O
M_r	437.48
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	10.2688 (4), 10.5322 (4), 11.2934 (4)
α, β, γ (°)	111.720 (2), 93.883 (2), 91.653 (3)
V (Å³)	1130.18 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.984, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	25456, 3992, 2997
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.129, 0.74
No. of reflections	3950
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.19

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Acknowledgements

The authors thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.

References

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Volume 1| Part 4| April 2016| x160526

doi:10.1107/S2414314616005265

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

5-Benzoyl-2-(1H-indol-3-yl)-4-(naphthalen-2-yl)-1H-pyrrole-3-carbo­nitrile

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

5-Benzoyl-2-(1H-indol-3-yl)-4-(naphthalen-2-yl)-1H-pyrrole-3-carbonitrile