organic compounds
5-Benzoyl-2-(1H-indol-3-yl)-4-(naphthalen-2-yl)-1H-pyrrole-3-carbonitrile
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
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 Np—H⋯O (p = pyrrole) hydrogen bonds, forming inversion dimers with R22(10) loops. These dimers are linked via pairs of Ni—H⋯Nc (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
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 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).
In the crystal, molecules are linked by pairs of Np—H⋯O (p = pyrrole) hydrogen bonds, forming inversion dimers with (10) loops (Table 1 and Fig. 2). These dimers are linked via pairs of Ni—H⋯Nc (i = indole and c = carbonitrile) hydrogen bonds, enclosing (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).
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 .
details for the title compound are summarized in Table 2
|
Structural data
CCDC reference: 1471048
10.1107/S2414314616005265/su4022sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616005265/su4022Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616005265/su4022Isup3.cml
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%).
Crystal data, data collection and structure
details for the title compound are summarized in Table 2.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
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.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).
In the crystal, molecules are linked by pairs of Np—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 Ni—H···Nc (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).
Data collection: APEX2 (Bruker, 2004); cell
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).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. |
C30H19N3O | Z = 2 |
Mr = 437.48 | F(000) = 456 |
Triclinic, P1 | Dx = 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 |
Bruker Kappa APEXII CCD diffractometer | 3992 independent reflections |
Radiation source: fine-focus sealed tube | 2997 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
ω and φ scan | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −12→12 |
Tmin = 0.984, Tmax = 0.987 | k = −12→12 |
25456 measured reflections | l = −13→13 |
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(Fo2) + (0.0737P)2 + 1.3759P] where P = (Fo2 + 2Fc2)/3 |
3950 reflections | (Δ/σ)max < 0.001 |
307 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C30H19N3O | γ = 91.653 (3)° |
Mr = 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)° |
Bruker Kappa APEXII CCD diffractometer | 3992 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 2997 reflections with I > 2σ(I) |
Tmin = 0.984, Tmax = 0.987 | Rint = 0.030 |
25456 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.129 | H-atom parameters constrained |
S = 0.74 | Δρmax = 0.15 e Å−3 |
3950 reflections | Δρmin = −0.19 e Å−3 |
307 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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) |
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. |
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 |
Mr | 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) |
Tmin, Tmax | 0.984, 0.987 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 25456, 3992, 2997 |
Rint | 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 |
Δρmax, Δρmin (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
Amal Raj, A., Raghunathan, R., Sridevikumar, M. R. & Raman, N. (2003). Bioorg. Med. Chem. 11, 407–419. Web of Science PubMed Google Scholar
Andreani, A., Granaiola, M., Leoni, A., Locatelli, A., Morigi, R., Rambaldi, M., Giorgi, G., Salvini, L. & Garaliene, V. (2001). Anticancer Drug. Des. 16, 167–174. Web of Science PubMed CAS Google Scholar
Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chai, H., Zhao, C., Zhao, C. & Gong, P. (2006). Bioorg. Med. Chem. 14, 911–917. Web of Science CrossRef PubMed CAS Google Scholar
Inglebert, S. A., Arun, Y., Sethusankar, K. & Perumal, P. T. (2013). Acta Cryst. E69, o1585. CSD CrossRef IUCr Journals Google Scholar
Quetin-Leclercq, J. (1994). J. Pharm. Belg. 49, 181–192. CAS PubMed Google Scholar
Rajeswaran, W. G., Labroo, R. B., Cohen, L. A. & King, M. M. (1999). J. Org. Chem. 64, 1369–1371. Web of Science CrossRef CAS Google Scholar
Rodriguez, J. G., Temprano, F., Esteban-Calderon, C., Martinez-Ripoll, M. & Garcia-Blanco, S. (1985). Tetrahedron, 41, 3813–3823. CSD CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Singh, U. P., Sarma, B. K., Mishra, P. K. & Ray, A. B. (2000). Fol. Microbiol. 45, 173–176. Web of Science CrossRef CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stevenson, G. I., Smith, A. L., Lewis, S. G., Michie, S. G., Neduvelil, J. G., Patel, S., Marwood, R., Patel, S. & Castro, J. L. (2000). Bioorg. Med. Chem. Lett. 10, 2697–2699. Web of Science CrossRef PubMed CAS Google Scholar
Vimala, G., Raja, J. K., Naaz, Y. A., Preumal, P. T. & SubbiahPandi, A. (2015). Acta Cryst. E71, o335–o336. Web of Science CSD CrossRef IUCr Journals Google Scholar
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