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

Muthuselvi, C.; Athimoolam, S.; Srinivasan, N.; Ravikumar, B.; Pandiarajan, S.; Krishnakumar, R.V.

doi:10.1107/S2414314618012865

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 9| September 2018| x181286

https://doi.org/10.1107/S2414314618012865

Open

access

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

C. Muthuselvi,^a S. Athimoolam,^b N. Srinivasan,^c ^* B. Ravikumar,^a S. Pandiarajan ^a and R. V. Krishnakumar ^c

^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

Edited by K. Fejfarova, Institute of Biotechnology CAS, Czech Republic (Received 21 August 2018; accepted 12 September 2018; online 18 September 2018)

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 crystal structure of the title compound has been determined (Fig. 1).

Figure 1
Displacement ellipsoid plot (50% probability level) of the title compound, showing the atom-labelling scheme. H atoms have been omitted for clarity.

The five-membered thiazole ring (S1/C17/C16/N3/C18) adopts an envelope conformation on S1 with puckering parameters 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 envelope conformation 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)°.

The 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⋯·N2^iv 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).

Table 1
Hydrogen-bond geometry (Å, °)

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⋯N2^iv	0.97	2.66	3.609 (4)	166
Symmetry codes: (i) $[-x+1, y, -z+{\script{3\over 2}}]$ ; (ii) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z+1; (iv) -x+1, -y, -z+1.

Figure 2
Part of the crystal structure of the title compound, showing the formation of R₂²(10) and R₂²(14) graph-set motifs. Dashed lines indicate hydrogen bonds. The fused indeno-quinoxaline rings and H atoms not involved in the hydrogen bonding have been omitted for the sake of clarity.

Figure 3
Part of the crystal structure of the title compound, showing the formation of R₂²(18) and R₂²(24) graph-set motifs. Dashed lines indicate hydrogen bonds. The H atoms not involved in the hydrogen bonding have been omitted for the sake of clarity.

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 refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₃₀H₂₄N₄O₂S
M_r	504.59
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	273
a, b, c (Å)	18.6131 (13), 18.2243 (13), 15.8867 (11)
β (°)	110.757 (1)
V (Å³)	5039.2 (6)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.16
Crystal size (mm)	0.30 × 0.16 × 0.12

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009 )
T_min, T_max	0.95, 1.0
No. of measured, independent and observed [I > 2σ(I)] reflections	26271, 5092, 3836
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.622

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.186, 1.03
No. of reflections	5092
No. of parameters	335
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.16
Computer programs: APEX2 and SAINT (Bruker, 2009), SHELXS2013 (Sheldrick, 2008 ), SHELXL2018 (Sheldrick, 2015 ), PLUTON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1867229

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314618012865/ff4027sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618012865/ff4027Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: 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).

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 top

Crystal data top

C₃₀H₂₄N₄O₂S	F(000) = 2112
M_r = 504.59	D_x = 1.330 Mg m⁻³ D_m = 1.32 Mg m⁻³ D_m 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

Data collection top

Bruker SMART APEXII CCD diffractometer	3836 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.028
φ and ω scans	θ_max = 26.3°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −23→23
T_min = 0.95, T_max = 1.0	k = −22→22
26271 measured reflections	l = −19→19
5092 independent reflections

Refinement top

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(F_o²) + (0.1079P)² + 2.3737P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
5092 reflections	Δρ_max = 0.52 e Å⁻³
335 parameters	Δρ_min = −0.16 e Å⁻³

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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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···N2^iv	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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.