organic compounds
Ethyl 6′-cyano-7′-phenyl-1′,6′,7′,7a'-tetrahydro-3′H-spiro[indeno[1,2-b]quinoxaline-11,5′-pyrrolo[1,2-c]thiazole-6′-carboxylate
aDepartment of Physics, Devanga Arts College, Aruppukottai 626 101, Tamilnadu, India, bDepartment of Physics, University College of Engineering, Anna University Constituent College, Konam 629 004, Nagercoil, Tamilnadu, India, and cDepartment of Physics, Thiagarajar College, Madurai 625 009, Tamilnadu, India
*Correspondence e-mail: vasan692000@yahoo.co.in
In the title compound, C22H22ClN4O2S, the angle between the mean planes of the indene ring and the quinoxaline ring system is 3.93 (11)°. The five-membered indene and thiazole rings both adopt envelope conformations while the pyrrole ring adopts a twisted conformation. The two acceptor O atoms form a chelated three-centred hydrogen bond with a phenyl C atom.
Keywords: crystal structure; hydrogen bonding; graph-set; quinoxaline; thiazole.
CCDC reference: 1867229
Structure description
Quinoxaline derivatives have attracted considerable attention due to their biological activities and use as anti-viral, anti-bacterial, anti-inflammatory, anti-protozaoal, anti cancer, anti depressant and anti-HIV agents. Drugs containing a quinoxaline core are under clinical trial for anticancer therapeutic purposes (Zhang et al., 2013). Indenoquinoxaline derivatives have found applications in dyes (Sehlstedt et al., 1998) and as organic semiconductors (Gazit et al., 1996). Moreover, thiazole derivatives are found to be antituberculous, bacteriostatic and fungistatic agents (Shao et al., 2004). A search in the CSD (version 5.39, update, May 2018; Groom et al., 2016) for structures of the title compound containing indene, quinoxaline pyrrolo and thiazole with no filters gave seven hits: DEHFUU (Muthuselvi et al., 2017), DOPYO,(Sivakumar et al., 2014), DUXPET (Malathi et al.,2015), FUQCAX (Hamzehloueian et al., 2015), NIKSOR (Suhitha et al., 2013a), NIKSUK (Suhitha et al., 2013b) and RENZUI (Muthuselvi et al., 2018). In view of the important biological activities of indenoquinoxaline-pyrolothiazole derivatives, the of the title compound has been determined (Fig. 1).
The five-membered thiazole ring (S1/C17/C16/N3/C18) adopts an Q(2) = 0.473 (2) Å and φ(2) = 358.2 (2)°. The pyrrole ring (N3/C1/C19/C23/C16) adopts a twisted conformation on C19—C23 with puckering amplitude Q(2) = 0.443 (3) Å and φ(2) = 82.6 (3)°. The five-membered indene ring (C1–C5) adopts an on C1 with puckering parameters Q(2) = 0.076 (3) Å and φ(2) = 182 (2)°, but the six-membered rings of both indene and quinoxaline does not show any significant deviation from planarity. The mean planes of indene and quinoxaline make an angle 3.93 (11)°.
on S1 with puckering parametersThe mean plane through the quinoxaline ring system and the fused indene ring makes dihedral angles of 76.36 (6) and 54.94 (8)°, respectively, with the mean planes through the pyrrole and thiazole rings.
In the crystal, pairs of C17—H117B⋯·N4i hydrogen bonds (Table 1) connect molecules into inversion dimers with an R22(14) motif while C21—H21B⋯·O1ii hydrogen bonds form an R22(10) graph-set motif. Together, these interactions lead to the formation of chains running along the c-axis direction (Fig. 2). The O atoms O1 and O2 form a chelated three-centered hydrogen bond with the phenyl carbon atom C27, leading to a dimeric R22(18) motif. The C18—H18B⋯·N2iv hydrogen bond forms an R22(24) graph-set motif. This C—H⋯·N hydrogen bond and the chelated three-centered C—H⋯·O hydrogen bonds lead to the formation of a linear chain extending along the b-axis direction (Fig. 3).
Synthesis and crystallization
Equimolar amounts of 11H-indeno[1,2-b]quinoxalin-11-one and thiazolidine-4-carboxylic acid were added to methanol (20 ml) and the mixture was refluxed in a water bath for 2 min. Then an equimolar amount of propyl (E)-2-cyano-3-(phenyl) acrylate was added to the reaction mixture and refluxing was continued until the completion of the reaction (monitored using TLC) after 4 h. The precipitated solid was filtered and washed with methanol to obtain the title compound. Colourless needle-shaped crystals were obtained by the slow evaporation of a chloroform solution.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1867229
https://doi.org/10.1107/S2414314618012865/ff4027sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618012865/ff4027Isup2.hkl
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: PLUTON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).C30H24N4O2S | F(000) = 2112 |
Mr = 504.59 | Dx = 1.330 Mg m−3 Dm = 1.32 Mg m−3 Dm measured by floatation method |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 18.6131 (13) Å | Cell parameters from 6051 reflections |
b = 18.2243 (13) Å | θ = 1.5–26.5° |
c = 15.8867 (11) Å | µ = 0.16 mm−1 |
β = 110.757 (1)° | T = 273 K |
V = 5039.2 (6) Å3 | Needle, colorless |
Z = 8 | 0.30 × 0.16 × 0.12 mm |
Bruker SMART APEXII CCD diffractometer | 3836 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.028 |
φ and ω scans | θmax = 26.3°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −23→23 |
Tmin = 0.95, Tmax = 1.0 | k = −22→22 |
26271 measured reflections | l = −19→19 |
5092 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.064 | H-atom parameters constrained |
wR(F2) = 0.186 | w = 1/[σ2(Fo2) + (0.1079P)2 + 2.3737P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
5092 reflections | Δρmax = 0.52 e Å−3 |
335 parameters | Δρmin = −0.16 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.30934 (4) | 0.17536 (4) | 0.57840 (5) | 0.0739 (3) | |
O1 | 0.45967 (11) | 0.30451 (11) | 0.37194 (12) | 0.0762 (5) | |
O2 | 0.57726 (10) | 0.25504 (11) | 0.43424 (11) | 0.0723 (5) | |
N1 | 0.61674 (11) | 0.13563 (12) | 0.64087 (13) | 0.0621 (5) | |
N2 | 0.61166 (12) | 0.04137 (12) | 0.49401 (14) | 0.0666 (5) | |
N3 | 0.45872 (10) | 0.18686 (11) | 0.61438 (12) | 0.0598 (5) | |
N4 | 0.63289 (13) | 0.31402 (15) | 0.64698 (17) | 0.0825 (7) | |
C1 | 0.48811 (12) | 0.18165 (13) | 0.54051 (14) | 0.0548 (5) | |
C2 | 0.43822 (13) | 0.14707 (13) | 0.44885 (14) | 0.0563 (5) | |
C3 | 0.48151 (13) | 0.09497 (14) | 0.42181 (15) | 0.0612 (6) | |
C4 | 0.55572 (13) | 0.08615 (13) | 0.49236 (15) | 0.0578 (5) | |
C5 | 0.56009 (12) | 0.13355 (13) | 0.56520 (15) | 0.0562 (5) | |
C6 | 0.67664 (13) | 0.08905 (14) | 0.64557 (16) | 0.0629 (6) | |
C7 | 0.67404 (13) | 0.04323 (14) | 0.57230 (17) | 0.0622 (6) | |
C8 | 0.73716 (15) | −0.00236 (16) | 0.5810 (2) | 0.0765 (7) | |
H8 | 0.736470 | −0.032498 | 0.533507 | 0.092* | |
C9 | 0.79906 (15) | −0.00253 (19) | 0.6585 (2) | 0.0869 (9) | |
H9 | 0.840694 | −0.032686 | 0.663610 | 0.104* | |
C10 | 0.80104 (15) | 0.0418 (2) | 0.7304 (2) | 0.0900 (9) | |
H10 | 0.843691 | 0.040567 | 0.783354 | 0.108* | |
C11 | 0.74084 (14) | 0.08723 (18) | 0.72407 (18) | 0.0806 (8) | |
H11 | 0.742915 | 0.116967 | 0.772452 | 0.097* | |
C12 | 0.36429 (14) | 0.16269 (15) | 0.39147 (16) | 0.0650 (6) | |
H12 | 0.334415 | 0.196494 | 0.408266 | 0.078* | |
C13 | 0.33503 (15) | 0.12760 (16) | 0.30874 (17) | 0.0719 (7) | |
H13 | 0.285422 | 0.138216 | 0.270113 | 0.086* | |
C14 | 0.37851 (17) | 0.07725 (18) | 0.28311 (18) | 0.0810 (8) | |
H14 | 0.358092 | 0.054641 | 0.227159 | 0.097* | |
C15 | 0.45188 (16) | 0.05996 (16) | 0.33932 (16) | 0.0716 (7) | |
H15 | 0.480913 | 0.025485 | 0.322203 | 0.086* | |
C16 | 0.43303 (13) | 0.26156 (14) | 0.62393 (15) | 0.0613 (6) | |
H16 | 0.469645 | 0.283697 | 0.678522 | 0.074* | |
C17 | 0.35336 (15) | 0.25831 (17) | 0.63304 (19) | 0.0755 (7) | |
H17A | 0.322730 | 0.300548 | 0.604378 | 0.091* | |
H17B | 0.358505 | 0.257668 | 0.695971 | 0.091* | |
C18 | 0.40462 (15) | 0.13219 (16) | 0.62071 (19) | 0.0725 (7) | |
H18A | 0.417100 | 0.116742 | 0.682696 | 0.087* | |
H18B | 0.405837 | 0.089559 | 0.584682 | 0.087* | |
C19 | 0.50524 (12) | 0.26528 (13) | 0.52728 (14) | 0.0559 (5) | |
C20 | 0.50988 (14) | 0.27817 (13) | 0.43387 (16) | 0.0595 (6) | |
C21 | 0.59318 (19) | 0.2614 (2) | 0.3500 (2) | 0.0898 (9) | |
H21A | 0.569101 | 0.221297 | 0.309738 | 0.108* | |
H21B | 0.572803 | 0.307257 | 0.319989 | 0.108* | |
C22 | 0.57810 (14) | 0.29091 (15) | 0.59573 (16) | 0.0628 (6) | |
C23 | 0.43634 (13) | 0.30320 (13) | 0.54228 (15) | 0.0579 (6) | |
H23 | 0.390463 | 0.288851 | 0.491480 | 0.070* | |
C24 | 0.43508 (13) | 0.38595 (14) | 0.54682 (17) | 0.0635 (6) | |
C25 | 0.48189 (15) | 0.42620 (17) | 0.6192 (2) | 0.0792 (8) | |
H25 | 0.517107 | 0.402287 | 0.668255 | 0.095* | |
C26 | 0.47659 (19) | 0.5021 (2) | 0.6190 (3) | 0.0985 (11) | |
H26 | 0.508978 | 0.529091 | 0.667254 | 0.118* | |
C27 | 0.4239 (2) | 0.5372 (2) | 0.5480 (3) | 0.1001 (11) | |
H27 | 0.420269 | 0.588046 | 0.548416 | 0.120* | |
C28 | 0.3769 (2) | 0.49888 (17) | 0.4773 (3) | 0.0904 (9) | |
H28 | 0.340960 | 0.523328 | 0.429366 | 0.108* | |
C29 | 0.38218 (16) | 0.42342 (15) | 0.4762 (2) | 0.0731 (7) | |
H29 | 0.349685 | 0.397341 | 0.427102 | 0.088* | |
C30 | 0.6754 (2) | 0.2591 (3) | 0.3728 (3) | 0.1403 (17) | |
H30A | 0.698959 | 0.296744 | 0.415987 | 0.210* | |
H30B | 0.687503 | 0.266864 | 0.319552 | 0.210* | |
H30C | 0.694450 | 0.211981 | 0.398039 | 0.210* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0546 (4) | 0.1003 (6) | 0.0709 (4) | −0.0089 (3) | 0.0272 (3) | 0.0014 (3) |
O1 | 0.0766 (12) | 0.0963 (13) | 0.0531 (9) | 0.0020 (10) | 0.0197 (9) | 0.0065 (9) |
O2 | 0.0684 (10) | 0.0938 (13) | 0.0640 (10) | 0.0025 (9) | 0.0349 (8) | 0.0006 (9) |
N1 | 0.0505 (10) | 0.0813 (14) | 0.0550 (11) | 0.0075 (9) | 0.0193 (9) | 0.0018 (9) |
N2 | 0.0626 (12) | 0.0781 (14) | 0.0654 (12) | −0.0012 (10) | 0.0304 (10) | −0.0021 (10) |
N3 | 0.0508 (10) | 0.0833 (14) | 0.0498 (10) | 0.0048 (9) | 0.0232 (8) | 0.0061 (9) |
N4 | 0.0566 (13) | 0.1076 (19) | 0.0755 (14) | −0.0109 (12) | 0.0137 (11) | −0.0064 (13) |
C1 | 0.0470 (11) | 0.0719 (15) | 0.0463 (11) | 0.0013 (10) | 0.0175 (9) | 0.0042 (10) |
C2 | 0.0551 (12) | 0.0683 (14) | 0.0481 (11) | −0.0080 (10) | 0.0214 (10) | 0.0027 (10) |
C3 | 0.0610 (13) | 0.0737 (15) | 0.0513 (12) | −0.0078 (11) | 0.0229 (10) | 0.0045 (11) |
C4 | 0.0575 (13) | 0.0670 (14) | 0.0559 (12) | −0.0020 (10) | 0.0287 (10) | 0.0029 (10) |
C5 | 0.0505 (12) | 0.0711 (15) | 0.0512 (12) | 0.0004 (10) | 0.0231 (10) | 0.0051 (10) |
C6 | 0.0500 (12) | 0.0808 (16) | 0.0623 (13) | 0.0050 (11) | 0.0253 (11) | 0.0062 (12) |
C7 | 0.0518 (12) | 0.0745 (15) | 0.0683 (14) | 0.0002 (11) | 0.0310 (11) | 0.0042 (12) |
C8 | 0.0600 (15) | 0.0912 (19) | 0.0889 (18) | 0.0045 (13) | 0.0395 (14) | −0.0050 (15) |
C9 | 0.0539 (15) | 0.110 (2) | 0.105 (2) | 0.0155 (15) | 0.0383 (15) | 0.0020 (18) |
C10 | 0.0512 (14) | 0.133 (3) | 0.0815 (18) | 0.0188 (15) | 0.0178 (13) | 0.0002 (18) |
C11 | 0.0555 (14) | 0.118 (2) | 0.0666 (15) | 0.0141 (14) | 0.0202 (12) | −0.0042 (15) |
C12 | 0.0557 (13) | 0.0815 (17) | 0.0549 (13) | −0.0072 (12) | 0.0159 (11) | 0.0068 (11) |
C13 | 0.0637 (15) | 0.0923 (19) | 0.0543 (13) | −0.0121 (13) | 0.0142 (12) | 0.0051 (13) |
C14 | 0.0829 (19) | 0.104 (2) | 0.0505 (13) | −0.0182 (16) | 0.0165 (13) | −0.0042 (14) |
C15 | 0.0804 (17) | 0.0837 (18) | 0.0555 (14) | −0.0095 (14) | 0.0299 (13) | −0.0073 (12) |
C16 | 0.0507 (12) | 0.0833 (16) | 0.0500 (12) | −0.0045 (11) | 0.0179 (10) | −0.0080 (11) |
C17 | 0.0632 (15) | 0.104 (2) | 0.0678 (15) | −0.0002 (14) | 0.0332 (12) | −0.0061 (14) |
C18 | 0.0722 (16) | 0.0829 (18) | 0.0721 (15) | 0.0038 (13) | 0.0374 (13) | 0.0158 (13) |
C19 | 0.0482 (11) | 0.0705 (15) | 0.0502 (12) | −0.0030 (10) | 0.0187 (9) | −0.0004 (10) |
C20 | 0.0605 (13) | 0.0682 (15) | 0.0527 (12) | −0.0086 (11) | 0.0237 (11) | −0.0053 (11) |
C21 | 0.097 (2) | 0.120 (3) | 0.0687 (17) | −0.0065 (18) | 0.0489 (16) | −0.0110 (16) |
C22 | 0.0526 (13) | 0.0817 (17) | 0.0562 (13) | −0.0019 (12) | 0.0219 (11) | −0.0003 (12) |
C23 | 0.0475 (11) | 0.0750 (15) | 0.0510 (12) | −0.0037 (10) | 0.0171 (9) | −0.0081 (10) |
C24 | 0.0508 (12) | 0.0759 (16) | 0.0714 (15) | −0.0082 (11) | 0.0310 (11) | −0.0120 (12) |
C25 | 0.0595 (14) | 0.090 (2) | 0.095 (2) | −0.0110 (13) | 0.0364 (14) | −0.0284 (16) |
C26 | 0.0746 (19) | 0.104 (3) | 0.136 (3) | −0.0325 (18) | 0.061 (2) | −0.056 (2) |
C27 | 0.099 (2) | 0.079 (2) | 0.153 (3) | −0.0158 (19) | 0.084 (3) | −0.020 (2) |
C28 | 0.106 (2) | 0.0700 (19) | 0.117 (2) | 0.0009 (17) | 0.066 (2) | −0.0001 (18) |
C29 | 0.0704 (16) | 0.0769 (18) | 0.0795 (17) | −0.0056 (13) | 0.0358 (14) | −0.0029 (14) |
C30 | 0.109 (3) | 0.219 (5) | 0.122 (3) | −0.036 (3) | 0.078 (3) | −0.039 (3) |
S1—C17 | 1.791 (3) | C13—H13 | 0.9300 |
S1—C18 | 1.836 (3) | C14—C15 | 1.377 (4) |
O1—C20 | 1.192 (3) | C14—H14 | 0.9300 |
O2—C20 | 1.321 (3) | C15—H15 | 0.9300 |
O2—C21 | 1.475 (3) | C16—C23 | 1.523 (3) |
N1—C5 | 1.288 (3) | C16—C17 | 1.541 (3) |
N1—C6 | 1.382 (3) | C16—H16 | 0.9800 |
N2—C4 | 1.316 (3) | C17—H17A | 0.9700 |
N2—C7 | 1.369 (3) | C17—H17B | 0.9700 |
N3—C18 | 1.445 (3) | C18—H18A | 0.9700 |
N3—C1 | 1.463 (3) | C18—H18B | 0.9700 |
N3—C16 | 1.468 (3) | C19—C22 | 1.481 (3) |
N4—C22 | 1.137 (3) | C19—C20 | 1.535 (3) |
C1—C5 | 1.531 (3) | C19—C23 | 1.548 (3) |
C1—C2 | 1.556 (3) | C21—C30 | 1.443 (5) |
C1—C19 | 1.586 (3) | C21—H21A | 0.9700 |
C2—C12 | 1.384 (3) | C21—H21B | 0.9700 |
C2—C3 | 1.407 (3) | C23—C24 | 1.510 (4) |
C3—C15 | 1.384 (3) | C23—H23 | 0.9800 |
C3—C4 | 1.447 (3) | C24—C25 | 1.382 (4) |
C4—C5 | 1.423 (3) | C24—C29 | 1.383 (4) |
C6—C11 | 1.389 (3) | C25—C26 | 1.387 (5) |
C6—C7 | 1.419 (4) | C25—H25 | 0.9300 |
C7—C8 | 1.405 (3) | C26—C27 | 1.363 (5) |
C8—C9 | 1.356 (4) | C26—H26 | 0.9300 |
C8—H8 | 0.9300 | C27—C28 | 1.348 (5) |
C9—C10 | 1.388 (4) | C27—H27 | 0.9300 |
C9—H9 | 0.9300 | C28—C29 | 1.379 (4) |
C10—C11 | 1.368 (4) | C28—H28 | 0.9300 |
C10—H10 | 0.9300 | C29—H29 | 0.9300 |
C11—H11 | 0.9300 | C30—H30A | 0.9600 |
C12—C13 | 1.388 (4) | C30—H30B | 0.9600 |
C12—H12 | 0.9300 | C30—H30C | 0.9600 |
C13—C14 | 1.377 (4) | ||
C17—S1—C18 | 88.14 (13) | C17—C16—H16 | 108.9 |
C20—O2—C21 | 117.8 (2) | C16—C17—S1 | 106.09 (18) |
C5—N1—C6 | 114.2 (2) | C16—C17—H17A | 110.5 |
C4—N2—C7 | 114.4 (2) | S1—C17—H17A | 110.5 |
C18—N3—C1 | 118.6 (2) | C16—C17—H17B | 110.5 |
C18—N3—C16 | 111.81 (18) | S1—C17—H17B | 110.5 |
C1—N3—C16 | 111.78 (18) | H17A—C17—H17B | 108.7 |
N3—C1—C5 | 111.94 (17) | N3—C18—S1 | 106.59 (18) |
N3—C1—C2 | 120.54 (18) | N3—C18—H18A | 110.4 |
C5—C1—C2 | 100.70 (18) | S1—C18—H18A | 110.4 |
N3—C1—C19 | 101.18 (18) | N3—C18—H18B | 110.4 |
C5—C1—C19 | 112.66 (17) | S1—C18—H18B | 110.4 |
C2—C1—C19 | 110.27 (17) | H18A—C18—H18B | 108.6 |
C12—C2—C3 | 118.7 (2) | C22—C19—C20 | 108.11 (18) |
C12—C2—C1 | 131.1 (2) | C22—C19—C23 | 109.83 (18) |
C3—C2—C1 | 110.03 (19) | C20—C19—C23 | 114.47 (19) |
C15—C3—C2 | 121.4 (2) | C22—C19—C1 | 112.36 (19) |
C15—C3—C4 | 129.3 (2) | C20—C19—C1 | 110.98 (18) |
C2—C3—C4 | 109.3 (2) | C23—C19—C1 | 101.08 (17) |
N2—C4—C5 | 122.9 (2) | O1—C20—O2 | 126.7 (2) |
N2—C4—C3 | 128.0 (2) | O1—C20—C19 | 124.3 (2) |
C5—C4—C3 | 109.0 (2) | O2—C20—C19 | 109.0 (2) |
N1—C5—C4 | 124.7 (2) | C30—C21—O2 | 107.8 (3) |
N1—C5—C1 | 125.1 (2) | C30—C21—H21A | 110.1 |
C4—C5—C1 | 110.28 (19) | O2—C21—H21A | 110.1 |
N1—C6—C11 | 119.0 (2) | C30—C21—H21B | 110.1 |
N1—C6—C7 | 121.6 (2) | O2—C21—H21B | 110.1 |
C11—C6—C7 | 119.4 (2) | H21A—C21—H21B | 108.5 |
N2—C7—C8 | 119.0 (2) | N4—C22—C19 | 176.6 (3) |
N2—C7—C6 | 122.1 (2) | C24—C23—C16 | 116.79 (19) |
C8—C7—C6 | 118.9 (2) | C24—C23—C19 | 118.75 (19) |
C9—C8—C7 | 120.2 (3) | C16—C23—C19 | 101.22 (18) |
C9—C8—H8 | 119.9 | C24—C23—H23 | 106.4 |
C7—C8—H8 | 119.9 | C16—C23—H23 | 106.4 |
C8—C9—C10 | 120.8 (3) | C19—C23—H23 | 106.4 |
C8—C9—H9 | 119.6 | C25—C24—C29 | 118.1 (3) |
C10—C9—H9 | 119.6 | C25—C24—C23 | 123.6 (3) |
C11—C10—C9 | 120.6 (3) | C29—C24—C23 | 118.2 (2) |
C11—C10—H10 | 119.7 | C24—C25—C26 | 120.3 (3) |
C9—C10—H10 | 119.7 | C24—C25—H25 | 119.9 |
C10—C11—C6 | 120.2 (3) | C26—C25—H25 | 119.9 |
C10—C11—H11 | 119.9 | C27—C26—C25 | 119.9 (3) |
C6—C11—H11 | 119.9 | C27—C26—H26 | 120.0 |
C2—C12—C13 | 119.6 (3) | C25—C26—H26 | 120.0 |
C2—C12—H12 | 120.2 | C28—C27—C26 | 120.7 (3) |
C13—C12—H12 | 120.2 | C28—C27—H27 | 119.6 |
C14—C13—C12 | 120.8 (3) | C26—C27—H27 | 119.6 |
C14—C13—H13 | 119.6 | C27—C28—C29 | 119.9 (4) |
C12—C13—H13 | 119.6 | C27—C28—H28 | 120.0 |
C15—C14—C13 | 120.8 (2) | C29—C28—H28 | 120.0 |
C15—C14—H14 | 119.6 | C28—C29—C24 | 121.0 (3) |
C13—C14—H14 | 119.6 | C28—C29—H29 | 119.5 |
C14—C15—C3 | 118.6 (3) | C24—C29—H29 | 119.5 |
C14—C15—H15 | 120.7 | C21—C30—H30A | 109.5 |
C3—C15—H15 | 120.7 | C21—C30—H30B | 109.5 |
N3—C16—C23 | 105.12 (17) | H30A—C30—H30B | 109.5 |
N3—C16—C17 | 109.5 (2) | C21—C30—H30C | 109.5 |
C23—C16—C17 | 115.5 (2) | H30A—C30—H30C | 109.5 |
N3—C16—H16 | 108.9 | H30B—C30—H30C | 109.5 |
C23—C16—H16 | 108.9 |
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17B···N4i | 0.97 | 2.65 | 3.560 (4) | 156 |
C21—H21B···O1ii | 0.97 | 2.89 | 3.399 (3) | 114 |
C27—H27···O1iii | 0.93 | 2.90 | 3.562 (4) | 129 |
C27—H27···O2iii | 0.93 | 2.87 | 3.798 (4) | 174 |
C18—H18B···N2iv | 0.97 | 2.66 | 3.609 (4) | 166 |
Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+1, y, −z+1/2; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y, −z+1. |
Acknowledgements
The authors thank the Sophisticated Analytical Instrumental Facility (SAIF), Indian Institute of Technology, Chennai for the data collection, the Management of Devanaga Arts College, Aruppuokottai, for their encouragement and the Management of Thiagarajar College, Madurai, for their financial support in establishing the Cambridge Structural Database facility.
References
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Gazit, A., App, H., McMahon, G., Chen, J., Levitzki, A. & Bohmer, F. D. (1996). J. Med. Chem. 39, 2170–2177. CrossRef CAS PubMed Web of Science Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hamzehloueian, M., Sarrafi, Y. & Aghaei, Z. (2015). RSC Adv. 5, 76368–76376. CrossRef Google Scholar
Malathi, K., Kanchithalaivan, S., Kumar, R. R., Almansour, A. I., Kumar, R. S. & Arumugam, N. (2015). Tetrahedron Lett. 56, 6132–6135. CrossRef Google Scholar
Muthuselvi, C., Muthu, M., Athimoolam, S., Ravikumar, B., Pandiarajan, S. & Krishnakumar, R. V. (2017). IUCrData, 2, x171305. Google Scholar
Muthuselvi, C., Muthu, M., Athimoolam, S., Ravikumar, B., Pandiarajan, S. & Krishnakumar, R. V. (2018). IUCrData, 3, x180238. Google Scholar
Sehlstedt, U., Aich, P., Bergman, J., Vallberg, H., Nordén, B. & Gräslund, A. (1998). J. Mol. Biol. 278, 31–56. Web of Science CrossRef CAS PubMed Google Scholar
Shao, L., Jin, Z., Liu, J.-B., Zhou, X., Zhang, Q., Hu, Y. & Fang, J.-X. (2004). Acta Cryst. E60, o2517–o2519. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sivakumar, N., Viswanathan, V., Rao, J. N. S., Raghunathan, R. & Velmurugan, D. (2014). Acta Cryst. E70, o1111–o1112. CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Suhitha, S., Gunasekaran, K., Gavaskar, D., Raghunathan, R. & Velmurugan, D. (2013a). Acta Cryst. E69, m501. CrossRef IUCr Journals Google Scholar
Suhitha, S., Gunasekaran, K., Sureshbabu, A. R., Raghunathan, R. & Velmurugan, D. (2013b). Acta Cryst. E69, m500. CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, Q., Zhai, S., Li, L., Li, X., Zhou, H., Liu, A., Su, G., Mu, Q., Du, Y. & Yan, B. (2013). Biochem. Pharmacol. 86, 351–360. CrossRef Google Scholar
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