organic compounds
4-[2-(1,3-Dioxoisoindolin-2-yl)-1,3-thiazol-4-yl]benzonitrile
aDrug Discovery Lab, Department of Chemistry, Annamalai University, Annamalainagar, Chidambaram 608 002, India, bDepartment of Pharmacology, PSG College of Pharmacy, Coimbatore 641 004, India, cDrug Discovery Laboratory, Life Sciences Division, Institute of Advanced Study in Science and Technology, Guwahati, Assam 781 035, India, and dPG & Research Department of Physics, Government Arts College, Melur 625 106, India
*Correspondence e-mail: profskabilan@gmail.com
The title isoindole, C18H8N3O2S, crystallizes with two independent molecules (A and B) in the whose geometrical features are similar. The benzonitrile ring is oriented at an angle of 2.1 (1)° (molecule A) and 16.0 (1)° (molecule B), with respect to the isoindole ring system. In the crystal, A molecules are linked via C—H⋯N hydrogen bonds, forming C(15) chains propagating along along the c axis. B molecules are linked via C—H⋯O interactions, forming dimers with an R22(10) graph-set motif. C—H⋯O and C—H⋯N interactions, charcterized by R22(15) and R21(7) motifs, are observed between molecules A and B.
CCDC reference: 1491736
Structure description
In a continuation of our work on the et al., 2016), we have undertaken a single-crystal X-ray diffraction study of the title compound which has confirmed the molecular structure and atomic connectivity, as illustrated in Fig. 1. The of contains two molecules (A and B) (Fig. 1); their corresponding bond lengths and bond angles are in good agreement. Fig. 2 shows a superposition of the two molecules using Qmol (Gans & Shalloway, 2001); the r.m.s. deviation is 0.2 Å.
analysis of isoindole derivatives (SaravananThe thiazole ring is planar with the maximum deviation of 0.001 (3) Å for atoms C9 and C9′ in molecules A and B. Keto atoms O2 and O3 deviate from the mean plane of the ring to which they are attached by 0.032 (2) and −0.044 (3) Å, respectively, in molecule A, −0.011 (3) and −0.122 (3) Å in molecule B. The nitrile group atoms (C18 and N1/C18′ and N1′) deviate by −0.036 (4) and −0.145 (2) Å, respectively, in molecule A, −0.015 (3) and −0.028 (3) Å in molecule B. The benzonitrile rings make dihedral angles of 4.2 (1) (molecule A) and 3.4 (1)° (molecule B) with thiazole rings. The benzonitrile ring in molecule A is oriented at an angle of 2.1 (1)° with respect to the isoindole ring system whereas it is oriented at an angle of 16.0 (1)° in molecule B.
The molecular structure is influenced by intramolecular C—H⋯N hydrogen bonds (Table 1). In the crystal, C13—H13⋯N3 hydrogen bonds link A molecules, forming C(15) chains propagating along the c axis; see Fig. 3. C12′—H12′⋯O2′ interactions form dimers of B molecules with graph-set motif R22(10). There are intermolecular interactions between molecules A and B: C2—H2⋯N3′ and C2′—H2′⋯O3 form an R22(15) ring, while C5′—H5′⋯O2 and C8′—H8′⋯O2 form an R12(7) ring; see Fig. 4.
Synthesis and crystallization
A mixture of 4-(2-aminothiazol-4-yl)benzonitrile (300 mg, 1.49 mmol), phthalic anhydride (441 mmol, 2.98 mmol) in glacial acetic acid (5 ml) was refluxed for 3 h. After cooling, the resulting solid was collected by filtration, washed with petroleum ether and dried under vacuum, giving the compound as a lemon-yellow solid. The solid was further recrystallized in DMF to yield yellow crystals of the title compound.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
|
Structural data
CCDC reference: 1491736
https://doi.org/10.1107/S2414314616011172/zp4007sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616011172/zp4007Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314616011172/zp4007Isup3.cml
Data collection: SMART (Bruker, 2002); cell
SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).C18H9N3O2S | Z = 4 |
Mr = 331.34 | F(000) = 680 |
Triclinic, P1 | Dx = 1.441 Mg m−3 |
a = 7.915 (7) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.1641 (10) Å | Cell parameters from 5982 reflections |
c = 17.255 (14) Å | θ = 3.3–26.7° |
α = 69.51 (2)° | µ = 0.23 mm−1 |
β = 79.50 (2)° | T = 296 K |
γ = 82.93 (3)° | Block, yellow |
V = 1527.0 (19) Å3 | 0.22 × 0.20 × 0.18 mm |
Bruker SMART APEX CCD area-detector diffractometer | Rint = 0.078 |
Radiation source: fine-focus sealed tube | θmax = 27.6°, θmin = 3.1° |
ω scans | h = −10→10 |
9065 measured reflections | k = −14→15 |
6901 independent reflections | l = −10→22 |
4330 reflections with I > 2σ(I) |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.058 | H-atom parameters constrained |
wR(F2) = 0.183 | w = 1/[σ2(Fo2) + (0.0829P)2 + 0.1516P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
6901 reflections | Δρmax = 0.23 e Å−3 |
433 parameters | Δρmin = −0.36 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 | 0.38921 (8) | 0.78889 (6) | 0.39010 (4) | 0.0571 (2) | |
O2 | 0.4162 (2) | 0.76188 (17) | 0.54965 (12) | 0.0647 (5) | |
O3 | 0.8033 (2) | 0.48462 (17) | 0.48373 (12) | 0.0654 (5) | |
N1 | 0.6111 (2) | 0.63277 (17) | 0.35764 (12) | 0.0464 (5) | |
N2 | 0.5965 (2) | 0.63508 (17) | 0.49470 (12) | 0.0438 (4) | |
N3 | 0.7847 (4) | 0.4946 (3) | −0.04423 (19) | 0.1041 (11) | |
C1 | 0.7234 (3) | 0.5651 (2) | 0.21528 (16) | 0.0545 (6) | |
H1 | 0.7776 | 0.5324 | 0.2625 | 0.065* | |
C2 | 0.7744 (4) | 0.5259 (3) | 0.14837 (16) | 0.0612 (7) | |
H2 | 0.8623 | 0.4672 | 0.1505 | 0.073* | |
C3 | 0.6945 (4) | 0.5743 (3) | 0.07798 (16) | 0.0581 (7) | |
C4 | 0.5645 (4) | 0.6618 (3) | 0.07480 (17) | 0.0614 (7) | |
H4 | 0.5111 | 0.6944 | 0.0273 | 0.074* | |
C5 | 0.5139 (4) | 0.7006 (2) | 0.14184 (16) | 0.0586 (7) | |
H5 | 0.4264 | 0.7597 | 0.1393 | 0.070* | |
C6 | 0.5924 (3) | 0.6524 (2) | 0.21352 (14) | 0.0467 (5) | |
C7 | 0.5361 (3) | 0.6902 (2) | 0.28647 (14) | 0.0448 (5) | |
C8 | 0.4156 (3) | 0.7758 (2) | 0.29379 (16) | 0.0551 (6) | |
H8 | 0.3542 | 0.8220 | 0.2513 | 0.066* | |
C9 | 0.5460 (3) | 0.6755 (2) | 0.41544 (14) | 0.0428 (5) | |
C10 | 0.5266 (3) | 0.6826 (2) | 0.55746 (15) | 0.0477 (5) | |
C11 | 0.6149 (3) | 0.6191 (2) | 0.62956 (15) | 0.0478 (6) | |
C12 | 0.5935 (4) | 0.6341 (3) | 0.70662 (16) | 0.0595 (7) | |
H12 | 0.5112 | 0.6885 | 0.7202 | 0.071* | |
C13 | 0.6988 (4) | 0.5651 (3) | 0.76203 (17) | 0.0662 (8) | |
H13 | 0.6893 | 0.5737 | 0.8142 | 0.079* | |
C14 | 0.8181 (4) | 0.4836 (3) | 0.74229 (18) | 0.0670 (8) | |
H14 | 0.8873 | 0.4380 | 0.7816 | 0.080* | |
C15 | 0.8387 (3) | 0.4669 (2) | 0.66527 (17) | 0.0600 (7) | |
H15 | 0.9191 | 0.4111 | 0.6523 | 0.072* | |
C16 | 0.7339 (3) | 0.5375 (2) | 0.60933 (15) | 0.0457 (5) | |
C17 | 0.7246 (3) | 0.5424 (2) | 0.52334 (15) | 0.0472 (5) | |
C18 | 0.7454 (4) | 0.5311 (3) | 0.00934 (18) | 0.0742 (9) | |
S1' | 0.37678 (10) | −0.06821 (7) | 0.74956 (5) | 0.0658 (2) | |
O2' | 0.4044 (3) | −0.0300 (2) | 0.89536 (15) | 0.0899 (7) | |
O3' | −0.0673 (3) | 0.1952 (2) | 0.79880 (13) | 0.0790 (6) | |
N1' | 0.1656 (2) | 0.10281 (18) | 0.68470 (12) | 0.0479 (5) | |
N2' | 0.1870 (2) | 0.08009 (18) | 0.82460 (13) | 0.0493 (5) | |
N3' | −0.0485 (4) | 0.2563 (3) | 0.24512 (17) | 0.0912 (9) | |
C1' | 0.0585 (3) | 0.1964 (2) | 0.52348 (16) | 0.0480 (5) | |
H1' | 0.0214 | 0.2343 | 0.5625 | 0.058* | |
C2' | 0.0002 (3) | 0.2396 (2) | 0.44717 (16) | 0.0517 (6) | |
H2' | −0.0755 | 0.3060 | 0.4349 | 0.062* | |
C3' | 0.0556 (3) | 0.1831 (2) | 0.38873 (16) | 0.0497 (6) | |
C4' | 0.1694 (3) | 0.0849 (2) | 0.40719 (16) | 0.0576 (6) | |
H4' | 0.2076 | 0.0477 | 0.3678 | 0.069* | |
C5' | 0.2258 (3) | 0.0424 (2) | 0.48295 (16) | 0.0548 (6) | |
H5' | 0.3016 | −0.0240 | 0.4949 | 0.066* | |
C6' | 0.1714 (3) | 0.0974 (2) | 0.54304 (15) | 0.0449 (5) | |
C7' | 0.2291 (3) | 0.0505 (2) | 0.62486 (15) | 0.0461 (5) | |
C8' | 0.3429 (3) | −0.0425 (2) | 0.65024 (17) | 0.0597 (7) | |
H8' | 0.3960 | −0.0870 | 0.6173 | 0.072* | |
C9' | 0.2308 (3) | 0.0485 (2) | 0.75202 (15) | 0.0473 (5) | |
C10' | 0.2784 (3) | 0.0368 (3) | 0.89290 (17) | 0.0601 (7) | |
C11' | 0.1890 (3) | 0.0870 (3) | 0.95609 (16) | 0.0561 (6) | |
C12' | 0.2259 (4) | 0.0738 (3) | 1.03407 (19) | 0.0738 (9) | |
H12' | 0.3198 | 0.0260 | 1.0550 | 0.089* | |
C13' | 0.1183 (5) | 0.1343 (3) | 1.07954 (19) | 0.0792 (9) | |
H13' | 0.1400 | 0.1267 | 1.1324 | 0.095* | |
C14' | −0.0192 (5) | 0.2052 (3) | 1.04946 (19) | 0.0765 (9) | |
H14' | −0.0889 | 0.2452 | 1.0818 | 0.092* | |
C15' | −0.0558 (4) | 0.2181 (3) | 0.97160 (18) | 0.0682 (8) | |
H15' | −0.1495 | 0.2662 | 0.9507 | 0.082* | |
C16' | 0.0499 (3) | 0.1579 (2) | 0.92597 (15) | 0.0528 (6) | |
C17' | 0.0407 (3) | 0.1526 (2) | 0.84234 (16) | 0.0541 (6) | |
C18' | −0.0037 (4) | 0.2253 (2) | 0.30838 (19) | 0.0634 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0587 (4) | 0.0613 (4) | 0.0521 (4) | 0.0151 (3) | −0.0127 (3) | −0.0241 (3) |
O2 | 0.0701 (11) | 0.0740 (13) | 0.0571 (12) | 0.0228 (10) | −0.0165 (9) | −0.0364 (10) |
O3 | 0.0708 (12) | 0.0683 (12) | 0.0598 (12) | 0.0211 (10) | −0.0134 (10) | −0.0317 (10) |
N1 | 0.0489 (11) | 0.0513 (11) | 0.0420 (11) | 0.0000 (9) | −0.0085 (9) | −0.0194 (9) |
N2 | 0.0465 (10) | 0.0470 (11) | 0.0399 (10) | 0.0023 (8) | −0.0081 (8) | −0.0179 (9) |
N3 | 0.131 (3) | 0.128 (3) | 0.0669 (18) | 0.038 (2) | −0.0350 (18) | −0.0558 (19) |
C1 | 0.0574 (14) | 0.0671 (16) | 0.0398 (13) | 0.0062 (12) | −0.0135 (11) | −0.0193 (12) |
C2 | 0.0624 (16) | 0.0743 (18) | 0.0465 (15) | 0.0122 (14) | −0.0104 (12) | −0.0242 (14) |
C3 | 0.0672 (16) | 0.0701 (17) | 0.0401 (14) | −0.0036 (14) | −0.0082 (12) | −0.0225 (13) |
C4 | 0.0690 (17) | 0.0734 (19) | 0.0437 (15) | 0.0025 (14) | −0.0187 (13) | −0.0194 (13) |
C5 | 0.0680 (16) | 0.0619 (16) | 0.0484 (15) | 0.0081 (13) | −0.0182 (13) | −0.0210 (13) |
C6 | 0.0498 (13) | 0.0526 (14) | 0.0380 (12) | −0.0076 (11) | −0.0083 (10) | −0.0131 (11) |
C7 | 0.0473 (12) | 0.0498 (13) | 0.0391 (12) | −0.0062 (10) | −0.0064 (10) | −0.0160 (11) |
C8 | 0.0599 (15) | 0.0584 (15) | 0.0458 (14) | 0.0052 (12) | −0.0161 (12) | −0.0150 (12) |
C9 | 0.0448 (12) | 0.0451 (12) | 0.0401 (12) | −0.0030 (10) | −0.0063 (10) | −0.0162 (10) |
C10 | 0.0484 (12) | 0.0521 (14) | 0.0467 (14) | 0.0027 (11) | −0.0087 (11) | −0.0229 (11) |
C11 | 0.0526 (13) | 0.0491 (13) | 0.0426 (13) | −0.0079 (11) | −0.0065 (11) | −0.0153 (11) |
C12 | 0.0742 (17) | 0.0638 (16) | 0.0431 (14) | −0.0063 (14) | −0.0049 (13) | −0.0225 (13) |
C13 | 0.085 (2) | 0.0716 (19) | 0.0431 (15) | −0.0184 (16) | −0.0138 (14) | −0.0137 (14) |
C14 | 0.0723 (18) | 0.0733 (19) | 0.0497 (16) | −0.0117 (15) | −0.0233 (14) | −0.0041 (14) |
C15 | 0.0589 (15) | 0.0610 (17) | 0.0550 (16) | −0.0002 (13) | −0.0147 (13) | −0.0113 (13) |
C16 | 0.0459 (12) | 0.0478 (13) | 0.0430 (13) | −0.0047 (10) | −0.0089 (10) | −0.0132 (11) |
C17 | 0.0458 (12) | 0.0448 (13) | 0.0497 (14) | 0.0022 (10) | −0.0080 (11) | −0.0157 (11) |
C18 | 0.092 (2) | 0.088 (2) | 0.0480 (16) | 0.0144 (18) | −0.0217 (15) | −0.0300 (16) |
S1' | 0.0709 (4) | 0.0651 (5) | 0.0625 (5) | 0.0207 (4) | −0.0220 (4) | −0.0252 (4) |
O2' | 0.0619 (12) | 0.137 (2) | 0.0828 (16) | 0.0369 (13) | −0.0346 (11) | −0.0536 (15) |
O3' | 0.0830 (13) | 0.0973 (16) | 0.0602 (13) | 0.0427 (12) | −0.0321 (11) | −0.0362 (12) |
N1' | 0.0455 (10) | 0.0549 (12) | 0.0451 (12) | 0.0023 (9) | −0.0078 (9) | −0.0202 (10) |
N2' | 0.0468 (10) | 0.0600 (13) | 0.0426 (11) | 0.0038 (9) | −0.0120 (9) | −0.0189 (10) |
N3' | 0.123 (2) | 0.087 (2) | 0.0622 (18) | −0.0089 (18) | −0.0356 (17) | −0.0122 (15) |
C1' | 0.0465 (12) | 0.0509 (14) | 0.0486 (14) | −0.0012 (10) | −0.0024 (11) | −0.0221 (11) |
C2' | 0.0477 (13) | 0.0487 (14) | 0.0556 (15) | −0.0002 (11) | −0.0061 (11) | −0.0157 (12) |
C3' | 0.0507 (13) | 0.0495 (14) | 0.0462 (14) | −0.0088 (11) | −0.0057 (11) | −0.0117 (11) |
C4' | 0.0651 (16) | 0.0614 (16) | 0.0491 (15) | 0.0014 (13) | −0.0037 (12) | −0.0261 (13) |
C5' | 0.0562 (14) | 0.0554 (15) | 0.0542 (15) | 0.0106 (12) | −0.0086 (12) | −0.0248 (13) |
C6' | 0.0415 (11) | 0.0464 (13) | 0.0461 (13) | −0.0059 (10) | −0.0009 (10) | −0.0167 (11) |
C7' | 0.0439 (12) | 0.0477 (13) | 0.0482 (14) | −0.0031 (10) | −0.0047 (10) | −0.0190 (11) |
C8' | 0.0642 (16) | 0.0601 (16) | 0.0586 (17) | 0.0122 (13) | −0.0121 (13) | −0.0285 (14) |
C9' | 0.0441 (12) | 0.0508 (14) | 0.0470 (14) | −0.0001 (10) | −0.0067 (11) | −0.0172 (11) |
C10' | 0.0473 (14) | 0.0809 (19) | 0.0542 (16) | 0.0007 (13) | −0.0172 (12) | −0.0222 (14) |
C11' | 0.0558 (14) | 0.0688 (17) | 0.0454 (14) | −0.0097 (13) | −0.0113 (12) | −0.0175 (13) |
C12' | 0.0722 (18) | 0.099 (2) | 0.0525 (17) | −0.0070 (17) | −0.0211 (15) | −0.0222 (17) |
C13' | 0.099 (2) | 0.099 (3) | 0.0463 (17) | −0.027 (2) | −0.0124 (17) | −0.0247 (17) |
C14' | 0.099 (2) | 0.080 (2) | 0.0518 (18) | −0.0114 (19) | −0.0020 (17) | −0.0272 (16) |
C15' | 0.0832 (19) | 0.0667 (18) | 0.0537 (17) | 0.0069 (15) | −0.0108 (15) | −0.0227 (14) |
C16' | 0.0605 (15) | 0.0552 (15) | 0.0418 (14) | −0.0055 (12) | −0.0070 (11) | −0.0152 (12) |
C17' | 0.0566 (14) | 0.0568 (15) | 0.0465 (14) | 0.0061 (12) | −0.0104 (12) | −0.0163 (12) |
C18' | 0.0736 (18) | 0.0568 (16) | 0.0574 (18) | −0.0089 (14) | −0.0114 (15) | −0.0138 (14) |
S1—C8 | 1.698 (3) | S1'—C8' | 1.697 (3) |
S1—C9 | 1.728 (3) | S1'—C9' | 1.724 (3) |
O2—C10 | 1.207 (3) | O2'—C10' | 1.204 (3) |
O3—C17 | 1.193 (3) | O3'—C17' | 1.190 (3) |
N1—C9 | 1.281 (3) | N1'—C9' | 1.284 (3) |
N1—C7 | 1.383 (3) | N1'—C7' | 1.384 (3) |
N2—C9 | 1.397 (3) | N2'—C10' | 1.404 (3) |
N2—C10 | 1.398 (3) | N2'—C9' | 1.408 (3) |
N2—C17 | 1.433 (3) | N2'—C17' | 1.421 (3) |
N3—C18 | 1.138 (4) | N3'—C18' | 1.131 (4) |
C1—C2 | 1.375 (4) | C1'—C2' | 1.378 (4) |
C1—C6 | 1.386 (3) | C1'—C6' | 1.387 (3) |
C1—H1 | 0.9300 | C1'—H1' | 0.9300 |
C2—C3 | 1.382 (4) | C2'—C3' | 1.389 (3) |
C2—H2 | 0.9300 | C2'—H2' | 0.9300 |
C3—C4 | 1.380 (4) | C3'—C4' | 1.384 (4) |
C3—C18 | 1.432 (4) | C3'—C18' | 1.444 (4) |
C4—C5 | 1.374 (4) | C4'—C5' | 1.363 (4) |
C4—H4 | 0.9300 | C4'—H4' | 0.9300 |
C5—C6 | 1.394 (3) | C5'—C6' | 1.400 (3) |
C5—H5 | 0.9300 | C5'—H5' | 0.9300 |
C6—C7 | 1.465 (3) | C6'—C7' | 1.461 (4) |
C7—C8 | 1.346 (3) | C7'—C8' | 1.353 (3) |
C8—H8 | 0.9300 | C8'—H8' | 0.9300 |
C10—C11 | 1.464 (3) | C10'—C11' | 1.463 (4) |
C11—C16 | 1.374 (3) | C11'—C16' | 1.374 (4) |
C11—C12 | 1.382 (3) | C11'—C12' | 1.380 (4) |
C12—C13 | 1.367 (4) | C12'—C13' | 1.374 (5) |
C12—H12 | 0.9300 | C12'—H12' | 0.9300 |
C13—C14 | 1.372 (4) | C13'—C14' | 1.363 (5) |
C13—H13 | 0.9300 | C13'—H13' | 0.9300 |
C14—C15 | 1.391 (4) | C14'—C15' | 1.377 (4) |
C14—H14 | 0.9300 | C14'—H14' | 0.9300 |
C15—C16 | 1.376 (4) | C15'—C16' | 1.367 (4) |
C15—H15 | 0.9300 | C15'—H15' | 0.9300 |
C16—C17 | 1.479 (3) | C16'—C17' | 1.482 (4) |
C8—S1—C9 | 87.83 (12) | C8'—S1'—C9' | 88.02 (12) |
C9—N1—C7 | 110.1 (2) | C9'—N1'—C7' | 110.2 (2) |
C9—N2—C10 | 123.2 (2) | C10'—N2'—C9' | 123.8 (2) |
C9—N2—C17 | 126.21 (19) | C10'—N2'—C17' | 110.2 (2) |
C10—N2—C17 | 110.61 (19) | C9'—N2'—C17' | 125.9 (2) |
C2—C1—C6 | 121.1 (2) | C2'—C1'—C6' | 121.1 (2) |
C2—C1—H1 | 119.4 | C2'—C1'—H1' | 119.4 |
C6—C1—H1 | 119.4 | C6'—C1'—H1' | 119.4 |
C1—C2—C3 | 119.7 (3) | C1'—C2'—C3' | 119.5 (2) |
C1—C2—H2 | 120.2 | C1'—C2'—H2' | 120.2 |
C3—C2—H2 | 120.2 | C3'—C2'—H2' | 120.2 |
C4—C3—C2 | 120.1 (2) | C4'—C3'—C2' | 119.9 (2) |
C4—C3—C18 | 120.5 (2) | C4'—C3'—C18' | 119.0 (2) |
C2—C3—C18 | 119.4 (3) | C2'—C3'—C18' | 121.0 (2) |
C5—C4—C3 | 120.0 (2) | C5'—C4'—C3' | 120.2 (2) |
C5—C4—H4 | 120.0 | C5'—C4'—H4' | 119.9 |
C3—C4—H4 | 120.0 | C3'—C4'—H4' | 119.9 |
C4—C5—C6 | 120.7 (3) | C4'—C5'—C6' | 121.0 (2) |
C4—C5—H5 | 119.6 | C4'—C5'—H5' | 119.5 |
C6—C5—H5 | 119.6 | C6'—C5'—H5' | 119.5 |
C1—C6—C5 | 118.4 (2) | C1'—C6'—C5' | 118.2 (2) |
C1—C6—C7 | 120.3 (2) | C1'—C6'—C7' | 120.8 (2) |
C5—C6—C7 | 121.3 (2) | C5'—C6'—C7' | 121.0 (2) |
C8—C7—N1 | 114.2 (2) | C8'—C7'—N1' | 114.0 (2) |
C8—C7—C6 | 127.5 (2) | C8'—C7'—C6' | 126.3 (2) |
N1—C7—C6 | 118.2 (2) | N1'—C7'—C6' | 119.7 (2) |
C7—C8—S1 | 111.79 (19) | C7'—C8'—S1' | 111.73 (19) |
C7—C8—H8 | 124.1 | C7'—C8'—H8' | 124.1 |
S1—C8—H8 | 124.1 | S1'—C8'—H8' | 124.1 |
N1—C9—N2 | 123.2 (2) | N1'—C9'—N2' | 123.1 (2) |
N1—C9—S1 | 116.02 (18) | N1'—C9'—S1' | 116.08 (18) |
N2—C9—S1 | 120.76 (16) | N2'—C9'—S1' | 120.86 (18) |
O2—C10—N2 | 124.1 (2) | O2'—C10'—N2' | 123.7 (3) |
O2—C10—C11 | 129.1 (2) | O2'—C10'—C11' | 129.4 (3) |
N2—C10—C11 | 106.7 (2) | N2'—C10'—C11' | 106.8 (2) |
C16—C11—C12 | 122.1 (2) | C16'—C11'—C12' | 120.7 (3) |
C16—C11—C10 | 108.7 (2) | C16'—C11'—C10' | 108.8 (2) |
C12—C11—C10 | 129.2 (2) | C12'—C11'—C10' | 130.4 (3) |
C13—C12—C11 | 117.0 (3) | C13'—C12'—C11' | 117.2 (3) |
C13—C12—H12 | 121.5 | C13'—C12'—H12' | 121.4 |
C11—C12—H12 | 121.5 | C11'—C12'—H12' | 121.4 |
C12—C13—C14 | 121.3 (3) | C14'—C13'—C12' | 122.0 (3) |
C12—C13—H13 | 119.3 | C14'—C13'—H13' | 119.0 |
C14—C13—H13 | 119.3 | C12'—C13'—H13' | 119.0 |
C13—C14—C15 | 122.0 (3) | C13'—C14'—C15' | 120.6 (3) |
C13—C14—H14 | 119.0 | C13'—C14'—H14' | 119.7 |
C15—C14—H14 | 119.0 | C15'—C14'—H14' | 119.7 |
C16—C15—C14 | 116.5 (3) | C16'—C15'—C14' | 117.9 (3) |
C16—C15—H15 | 121.8 | C16'—C15'—H15' | 121.1 |
C14—C15—H15 | 121.8 | C14'—C15'—H15' | 121.1 |
C11—C16—C15 | 121.2 (2) | C15'—C16'—C11' | 121.5 (3) |
C11—C16—C17 | 109.0 (2) | C15'—C16'—C17' | 129.9 (3) |
C15—C16—C17 | 129.8 (2) | C11'—C16'—C17' | 108.5 (2) |
O3—C17—N2 | 125.4 (2) | O3'—C17'—N2' | 125.6 (2) |
O3—C17—C16 | 129.7 (2) | O3'—C17'—C16' | 128.8 (2) |
N2—C17—C16 | 104.86 (19) | N2'—C17'—C16' | 105.6 (2) |
N3—C18—C3 | 178.6 (4) | N3'—C18'—C3' | 178.5 (3) |
C6—C1—C2—C3 | 0.1 (4) | C6'—C1'—C2'—C3' | 0.0 (4) |
C1—C2—C3—C4 | 0.3 (4) | C1'—C2'—C3'—C4' | −0.6 (4) |
C1—C2—C3—C18 | −178.5 (3) | C1'—C2'—C3'—C18' | 179.5 (2) |
C2—C3—C4—C5 | −0.3 (4) | C2'—C3'—C4'—C5' | 0.8 (4) |
C18—C3—C4—C5 | 178.5 (3) | C18'—C3'—C4'—C5' | −179.3 (2) |
C3—C4—C5—C6 | −0.1 (4) | C3'—C4'—C5'—C6' | −0.5 (4) |
C2—C1—C6—C5 | −0.5 (4) | C2'—C1'—C6'—C5' | 0.3 (4) |
C2—C1—C6—C7 | 178.0 (2) | C2'—C1'—C6'—C7' | −178.4 (2) |
C4—C5—C6—C1 | 0.5 (4) | C4'—C5'—C6'—C1' | −0.1 (4) |
C4—C5—C6—C7 | −178.0 (2) | C4'—C5'—C6'—C7' | 178.7 (2) |
C9—N1—C7—C8 | 0.2 (3) | C9'—N1'—C7'—C8' | −0.5 (3) |
C9—N1—C7—C6 | −179.2 (2) | C9'—N1'—C7'—C6' | 179.6 (2) |
C1—C6—C7—C8 | 177.7 (2) | C1'—C6'—C7'—C8' | −177.6 (2) |
C5—C6—C7—C8 | −3.9 (4) | C5'—C6'—C7'—C8' | 3.7 (4) |
C1—C6—C7—N1 | −3.1 (3) | C1'—C6'—C7'—N1' | 2.3 (3) |
C5—C6—C7—N1 | 175.4 (2) | C5'—C6'—C7'—N1' | −176.4 (2) |
N1—C7—C8—S1 | −0.1 (3) | N1'—C7'—C8'—S1' | −0.4 (3) |
C6—C7—C8—S1 | 179.19 (19) | C6'—C7'—C8'—S1' | 179.53 (19) |
C9—S1—C8—C7 | 0.0 (2) | C9'—S1'—C8'—C7' | 0.9 (2) |
C7—N1—C9—N2 | −180.0 (2) | C7'—N1'—C9'—N2' | −178.4 (2) |
C7—N1—C9—S1 | −0.2 (3) | C7'—N1'—C9'—S1' | 1.2 (3) |
C10—N2—C9—N1 | 179.4 (2) | C10'—N2'—C9'—N1' | −167.8 (2) |
C17—N2—C9—N1 | −0.1 (4) | C17'—N2'—C9'—N1' | 16.6 (4) |
C10—N2—C9—S1 | −0.4 (3) | C10'—N2'—C9'—S1' | 12.6 (3) |
C17—N2—C9—S1 | −179.84 (17) | C17'—N2'—C9'—S1' | −162.98 (19) |
C8—S1—C9—N1 | 0.1 (2) | C8'—S1'—C9'—N1' | −1.2 (2) |
C8—S1—C9—N2 | 179.9 (2) | C8'—S1'—C9'—N2' | 178.4 (2) |
C9—N2—C10—O2 | 0.4 (4) | C9'—N2'—C10'—O2' | 1.1 (4) |
C17—N2—C10—O2 | 179.9 (2) | C17'—N2'—C10'—O2' | 177.3 (3) |
C9—N2—C10—C11 | −178.65 (19) | C9'—N2'—C10'—C11' | −178.0 (2) |
C17—N2—C10—C11 | 0.8 (3) | C17'—N2'—C10'—C11' | −1.8 (3) |
O2—C10—C11—C16 | −178.6 (3) | O2'—C10'—C11'—C16' | −179.3 (3) |
N2—C10—C11—C16 | 0.4 (3) | N2'—C10'—C11'—C16' | −0.3 (3) |
O2—C10—C11—C12 | 0.2 (5) | O2'—C10'—C11'—C12' | 1.7 (5) |
N2—C10—C11—C12 | 179.2 (2) | N2'—C10'—C11'—C12' | −179.3 (3) |
C16—C11—C12—C13 | 1.2 (4) | C16'—C11'—C12'—C13' | 0.0 (4) |
C10—C11—C12—C13 | −177.5 (2) | C10'—C11'—C12'—C13' | 179.0 (3) |
C11—C12—C13—C14 | −1.1 (4) | C11'—C12'—C13'—C14' | −0.3 (5) |
C12—C13—C14—C15 | 0.2 (4) | C12'—C13'—C14'—C15' | 0.4 (5) |
C13—C14—C15—C16 | 0.5 (4) | C13'—C14'—C15'—C16' | −0.1 (5) |
C12—C11—C16—C15 | −0.4 (4) | C14'—C15'—C16'—C11' | −0.2 (4) |
C10—C11—C16—C15 | 178.5 (2) | C14'—C15'—C16'—C17' | 178.5 (3) |
C12—C11—C16—C17 | 179.6 (2) | C12'—C11'—C16'—C15' | 0.3 (4) |
C10—C11—C16—C17 | −1.5 (3) | C10'—C11'—C16'—C15' | −178.9 (2) |
C14—C15—C16—C11 | −0.5 (4) | C12'—C11'—C16'—C17' | −178.7 (3) |
C14—C15—C16—C17 | 179.5 (2) | C10'—C11'—C16'—C17' | 2.1 (3) |
C9—N2—C17—O3 | −2.0 (4) | C10'—N2'—C17'—O3' | −174.7 (3) |
C10—N2—C17—O3 | 178.5 (2) | C9'—N2'—C17'—O3' | 1.4 (4) |
C9—N2—C17—C16 | 177.8 (2) | C10'—N2'—C17'—C16' | 3.0 (3) |
C10—N2—C17—C16 | −1.7 (2) | C9'—N2'—C17'—C16' | 179.1 (2) |
C11—C16—C17—O3 | −178.3 (3) | C15'—C16'—C17'—O3' | −4.4 (5) |
C15—C16—C17—O3 | 1.8 (4) | C11'—C16'—C17'—O3' | 174.5 (3) |
C11—C16—C17—N2 | 1.9 (3) | C15'—C16'—C17'—N2' | 178.0 (3) |
C15—C16—C17—N2 | −178.0 (2) | C11'—C16'—C17'—N2' | −3.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···N1 | 0.93 | 2.48 | 2.818 (4) | 102 |
C1′—H1′···N1′ | 0.93 | 2.52 | 2.856 (4) | 101 |
C2—H2···N3′i | 0.93 | 2.61 | 3.376 (4) | 141 |
C13—H13···N3ii | 0.93 | 2.51 | 3.324 (5) | 146 |
C5′—H5′···O2iii | 0.93 | 2.55 | 3.444 (3) | 161 |
C8′—H8′···O2iii | 0.93 | 2.48 | 3.346 (3) | 156 |
C12′—H12′···O2′iv | 0.93 | 2.50 | 3.285 (4) | 143 |
C2′—H2′···O3v | 0.93 | 2.61 | 3.395 (3) | 142 |
Symmetry codes: (i) x+1, y, z; (ii) x, y, z+1; (iii) x, y−1, z; (iv) −x+1, −y, −z+2; (v) x−1, y, z. |
Footnotes
‡Additional correspondence author, e-mail: s_selvanayagam@rediffmail.com.
Acknowledgements
The authors are thankful for funding support from the Department of Biotechnology North East Collaboration (DBT NEC) Research Project, grant No. BT/252/NE/TBP/2011, New Delhi, India.
References
Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gans, J. D. & Shalloway, D. (2001). J. Mol. Graph. Model. 19, 557–559. Web of Science CrossRef PubMed CAS Google Scholar
Saravanan, K., Archana, K., Lakshmithendral, K., Kabilan, S. & Selvanayagam, S. (2016). IUCrData 1, x161053. 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
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals 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.