organic compounds
(R*)-1-Benzyl-3-(2-hydroxyphenyl)indoline-2-one
aDepartment of Physics, S.D.N.B. Vaishnav College for Women, Chrompet, Chennai 600 044, India, and bIndustrial Chemistry Polymer Division, CSIR Central Leather Research Institute, Adyar, Chennai 600 020, India
*Correspondence e-mail: lakssdnbvc@gmail.com
The title compound, C21H17NO2, crystallizes with two independent molecules (A and B) in the The indoline ring system is almost planar in both molecules (r.m.s. deviations = 0.020 and 0.024 Å for molecules A and B, respectively). The benzyl and phenol rings are inclined to the indole ring system by 80.39 (12) and 68.39 (12)° in molecule A, and by 79.90 (13) and 74.88 (10)° in molecule B. The aryl rings are inclined to one another by 33.30 (14) and 30.62 (14)° in molecules A and B, respectively. In the crystal, A molecules are linked by pairs of O—H⋯O hydrogen bonds, forming inversion dimers. The same situation is observed for the B molecules and both sets of inversion dimers enclose R22(14) ring motifs. These dimers stack along the a-axis direction and are linked by offset π–π interactions [intercentroid distance = 3.6802 (13) Å] involving A and B indole ring systems, forming layers parallel to the ab plane.
Keywords: crystal structure; isatin; O—H⋯O hydrogen bonds; π–π interactions.
CCDC reference: 1530740
Structure description
Isatin is a starting material for the synthesis of a number of organic compounds (Hajare & Chavan, 2014). Isatin and its metabolites are constituents of many natural substances (Medvedev et al., 2007). It is found in humans and acts as a metabolic derivative of adrenaline (Sonawane & Tripathi, 2013). It exhibits endogamous activity in mammals (Chaudhary et al., 2013) and has shown cardioinhibitory effects on a frog's heart, and hypotensive, respiratory depression and antidiuretic effects (Pandeya et al., 2005). Isatin also possess anticancer (Khan et al., 2015), antioxidant (Sammaiah & Pragathi, 2014), antiviral (Gomathi et al., 2013), antimicrobial (Saxena et al., 2015), analgesic (Pal et al., 201), anti-inflammatory (Hajare & Chinchole, 2013), antitubercular (Aboul-fadl & Bin-Jubair, 2010), anticonvulsant (Raj, 2012) and antianxiety (Grewal, 2014) activities.
The title compound, crystallizes with two independent molecules (A and B) in the (Fig. 1). The indoline ring system is nearly planar in both molecules, the largest deviation from the mean plane being 0.042 (2) Å for atom C7 in molecule A and 0.080 (2) Å for atom O3 in molecule B. The dihedral angle between the isatin group and the phenol and benzyl rings are, respectively, 68.39 (12) and 80.39 (12)° for molecule A and 74.88 (10) and 79.90 (13)° for molecule B. The dihedral angle between the aryl rings is 33.30 (14)° for molecule A and 30.62 (14)° for molecule B.
In the crystal, the A molecules are linked by pairs of O—H⋯O hydrogen bonds, forming A–A inversion dimers. Likewise, the B molecules are also linked by a pair of O—H⋯O hydrogen bonds, forming B–B inversion dimers (see Table 1 and Fig. 2). Both dimers enclose (14) ring motifs. These dimers stack along the a-axis direction and are linked by offset π–π interactions, involving A and B indole ring systems (Fig. 3), forming layers parallel to the ab plane [Cg1⋯Cg2i = 3.743 (1) Å, interplanar distance = 3.557 (1) Å, Cg1 and Cg2 are the centroids of the indole rings N1/C5–C8 and N2/C26–C29, respectively; symmetry code: (i) x, y, z].
Synthesis and crystallization
An isatin-based MBH of adduct 1-benzyl-3-hydroxy-3-(6-oxocyclohex-1-en-1-yl)indolin-2-one (200 mg, 0.5 mmol, 1.0 equiv.) in 15 ml of dry dichloromethane was deposited dropwise in a flame-dried round-bottom flask equipped with a magnetic stirring bar and the solution was stirred vigorously to obtain a homogenous mixture. The resulting solution was purged with nitrogen gas for 15 min. Trifluoroacetic anhydride (0.06 ml, 0.12 mmol, and 1.5 equiv) was added dropwise to the reaction mixture and then dimethylaminopyridine (20 mg, 30 mol %) was added dropwise at 273 K. The reaction mixture was gradually brought to room temperature and stirred for a further 5 h. After completion of the reaction (monitored by TLC), the mixture was diluted with CH2Cl2 and the organic layer was washed sequentially with 2 N HCl solution, H2O, and brine, then dried over Na2SO4, filtered and concentrated under reduced pressure. It was then purified by silica gel using hexane: EtOAc (8:2) as and afforded the title compound. Colourless block-like crystals were obtained by slow evaporation of a solution in CH2Cl2:acetonitrile (1:1, v/v).
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1530740
https://doi.org/10.1107/S2414314617011646/su4159sup1.cif
contains datablocks I, Global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617011646/su4159Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617011646/su4159Isup3.cml
Data collection: APEX2 (Bruker, 2004); cell
SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek,2009); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015), PLATON (Spek, 2009) and publCIF (Westrip, 2010).C21H17NO2 | Z = 4 |
Mr = 315.36 | F(000) = 664 |
Triclinic, P1 | Dx = 1.278 Mg m−3 |
a = 11.1344 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.0889 (5) Å | Cell parameters from 8113 reflections |
c = 12.4679 (6) Å | θ = 2.4–25.7° |
α = 89.171 (3)° | µ = 0.08 mm−1 |
β = 79.125 (3)° | T = 296 K |
γ = 84.202 (3)° | Block, colourless |
V = 1639.62 (14) Å3 | 0.35 × 0.25 × 0.20 mm |
Bruker Kappa APEXII CCD diffractometer | 3525 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.035 |
ω and φ scan | θmax = 25.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −13→13 |
Tmin = 0.972, Tmax = 0.984 | k = −14→14 |
26691 measured reflections | l = −14→14 |
5763 independent reflections |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.197 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.1204P)2 + 0.1554P] where P = (Fo2 + 2Fc2)/3 |
5763 reflections | (Δ/σ)max < 0.001 |
433 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.20 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 | ||
O4 | 0.46387 (17) | 0.61250 (15) | 0.44690 (15) | 0.0685 (5) | |
H4 | 0.492150 | 0.577156 | 0.390610 | 0.103* | |
N2 | 0.38028 (18) | 0.69335 (16) | 0.82332 (15) | 0.0503 (5) | |
O3 | 0.43219 (19) | 0.54674 (15) | 0.70547 (15) | 0.0718 (6) | |
C26 | 0.3491 (2) | 0.80907 (19) | 0.8179 (2) | 0.0484 (6) | |
C37 | 0.5165 (2) | 0.74505 (18) | 0.56209 (18) | 0.0456 (6) | |
C28 | 0.3937 (2) | 0.73869 (19) | 0.63812 (19) | 0.0494 (6) | |
H28 | 0.330556 | 0.724990 | 0.596145 | 0.059* | |
C27 | 0.3521 (2) | 0.8390 (2) | 0.7102 (2) | 0.0501 (6) | |
C42 | 0.5483 (2) | 0.67851 (19) | 0.46908 (19) | 0.0489 (6) | |
C29 | 0.4045 (2) | 0.6465 (2) | 0.7224 (2) | 0.0522 (6) | |
C31 | 0.4977 (2) | 0.65051 (19) | 0.97035 (19) | 0.0486 (6) | |
C41 | 0.6625 (3) | 0.6816 (2) | 0.4024 (2) | 0.0590 (7) | |
H41 | 0.684161 | 0.636726 | 0.340486 | 0.071* | |
C5 | 0.0533 (2) | 0.7082 (2) | 0.8208 (3) | 0.0636 (7) | |
O1 | 0.0392 (2) | 0.80217 (16) | 0.5609 (2) | 0.0898 (7) | |
O2 | −0.00597 (18) | 1.06347 (16) | 0.61019 (19) | 0.0867 (7) | |
H2 | −0.016343 | 1.115971 | 0.569435 | 0.130* | |
C30 | 0.3871 (2) | 0.6317 (2) | 0.9235 (2) | 0.0550 (6) | |
H30A | 0.388706 | 0.552929 | 0.908650 | 0.066* | |
H30B | 0.313738 | 0.653266 | 0.977235 | 0.066* | |
C10 | −0.0150 (2) | 0.5262 (2) | 0.6615 (2) | 0.0570 (7) | |
C16 | −0.1160 (2) | 0.9517 (2) | 0.7407 (2) | 0.0609 (7) | |
N1 | 0.0688 (2) | 0.69565 (18) | 0.7074 (2) | 0.0666 (6) | |
C25 | 0.3207 (2) | 0.8848 (2) | 0.9022 (2) | 0.0591 (7) | |
H25 | 0.319239 | 0.862822 | 0.974243 | 0.071* | |
C21 | −0.1169 (3) | 1.0392 (2) | 0.6678 (2) | 0.0667 (8) | |
C38 | 0.6004 (2) | 0.8135 (2) | 0.5845 (2) | 0.0580 (7) | |
H38 | 0.579726 | 0.858638 | 0.646359 | 0.070* | |
C8 | 0.0386 (2) | 0.7933 (2) | 0.6585 (3) | 0.0689 (8) | |
C40 | 0.7439 (3) | 0.7510 (2) | 0.4276 (2) | 0.0677 (8) | |
H40 | 0.820268 | 0.752820 | 0.382363 | 0.081* | |
C7 | 0.0038 (2) | 0.8830 (2) | 0.7478 (2) | 0.0648 (7) | |
H7 | 0.068746 | 0.933263 | 0.737248 | 0.078* | |
C22 | 0.3256 (2) | 0.9492 (2) | 0.6852 (2) | 0.0632 (7) | |
H22 | 0.327328 | 0.971179 | 0.613131 | 0.076* | |
C24 | 0.2945 (3) | 0.9949 (2) | 0.8759 (3) | 0.0694 (8) | |
H24 | 0.275422 | 1.048307 | 0.931109 | 0.083* | |
C11 | −0.0165 (3) | 0.4223 (2) | 0.7062 (2) | 0.0683 (8) | |
H11 | 0.051960 | 0.390760 | 0.732365 | 0.082* | |
C17 | −0.2264 (3) | 0.9277 (2) | 0.8038 (2) | 0.0690 (8) | |
H17 | −0.227202 | 0.869856 | 0.853875 | 0.083* | |
C6 | 0.0122 (2) | 0.8185 (2) | 0.8486 (3) | 0.0643 (7) | |
C39 | 0.7136 (3) | 0.8171 (2) | 0.5184 (2) | 0.0672 (8) | |
H39 | 0.768729 | 0.864014 | 0.535308 | 0.081* | |
C13 | −0.2193 (3) | 0.4095 (3) | 0.6766 (2) | 0.0700 (8) | |
H13 | −0.287695 | 0.370238 | 0.681014 | 0.084* | |
C18 | −0.3357 (3) | 0.9886 (3) | 0.7934 (3) | 0.0802 (9) | |
H18 | −0.409399 | 0.972573 | 0.836734 | 0.096* | |
C1 | −0.0093 (3) | 0.8493 (3) | 0.9580 (3) | 0.0779 (9) | |
H1 | −0.038062 | 0.922200 | 0.978999 | 0.093* | |
C36 | 0.4861 (3) | 0.6869 (2) | 1.0755 (2) | 0.0718 (8) | |
H36 | 0.408038 | 0.702398 | 1.117624 | 0.086* | |
C2 | 0.0125 (3) | 0.7706 (3) | 1.0350 (3) | 0.0879 (10) | |
H2A | −0.001137 | 0.790974 | 1.108236 | 0.106* | |
C20 | −0.2257 (3) | 1.0979 (2) | 0.6558 (3) | 0.0780 (9) | |
H20 | −0.225973 | 1.154959 | 0.605021 | 0.094* | |
C23 | 0.2962 (3) | 1.0267 (2) | 0.7696 (3) | 0.0726 (8) | |
H23 | 0.277373 | 1.101192 | 0.753898 | 0.087* | |
C4 | 0.0742 (3) | 0.6298 (3) | 0.8971 (3) | 0.0727 (8) | |
H4A | 0.101207 | 0.556516 | 0.876558 | 0.087* | |
C9 | 0.0963 (3) | 0.5902 (2) | 0.6491 (3) | 0.0709 (8) | |
H9A | 0.161286 | 0.545878 | 0.676735 | 0.085* | |
H9B | 0.125575 | 0.603928 | 0.572233 | 0.085* | |
C3 | 0.0542 (3) | 0.6621 (3) | 1.0051 (3) | 0.0835 (9) | |
H3 | 0.068983 | 0.610288 | 1.058122 | 0.100* | |
C19 | −0.3343 (3) | 1.0721 (3) | 0.7191 (3) | 0.0841 (10) | |
H19 | −0.407784 | 1.112389 | 0.710997 | 0.101* | |
C32 | 0.6145 (3) | 0.6286 (3) | 0.9098 (3) | 0.0751 (8) | |
H32 | 0.625252 | 0.603469 | 0.838144 | 0.090* | |
C15 | −0.1186 (3) | 0.5711 (2) | 0.6259 (2) | 0.0710 (8) | |
H15 | −0.120036 | 0.642028 | 0.595998 | 0.085* | |
C12 | −0.1174 (3) | 0.3632 (2) | 0.7134 (3) | 0.0777 (9) | |
H12 | −0.116115 | 0.292220 | 0.743091 | 0.093* | |
C14 | −0.2197 (3) | 0.5139 (3) | 0.6335 (2) | 0.0761 (8) | |
H14 | −0.289045 | 0.546281 | 0.609107 | 0.091* | |
C35 | 0.5864 (4) | 0.7011 (3) | 1.1198 (3) | 0.0973 (12) | |
H35 | 0.575943 | 0.725624 | 1.191677 | 0.117* | |
C33 | 0.7156 (3) | 0.6440 (3) | 0.9551 (4) | 0.0982 (12) | |
H33 | 0.794259 | 0.629754 | 0.913735 | 0.118* | |
C34 | 0.7003 (4) | 0.6798 (3) | 1.0604 (5) | 0.1030 (14) | |
H34 | 0.768506 | 0.689614 | 1.091063 | 0.124* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O4 | 0.0774 (13) | 0.0655 (12) | 0.0685 (12) | −0.0134 (10) | −0.0242 (10) | −0.0221 (9) |
N2 | 0.0550 (12) | 0.0461 (12) | 0.0513 (12) | −0.0111 (9) | −0.0102 (10) | −0.0048 (9) |
O3 | 0.1073 (16) | 0.0436 (11) | 0.0650 (12) | −0.0164 (10) | −0.0124 (10) | −0.0084 (8) |
C26 | 0.0399 (13) | 0.0483 (14) | 0.0569 (15) | −0.0079 (10) | −0.0066 (11) | −0.0065 (11) |
C37 | 0.0500 (14) | 0.0419 (13) | 0.0478 (13) | −0.0053 (10) | −0.0160 (11) | −0.0022 (10) |
C28 | 0.0519 (14) | 0.0496 (14) | 0.0507 (14) | −0.0110 (11) | −0.0163 (11) | −0.0057 (11) |
C27 | 0.0426 (13) | 0.0500 (14) | 0.0578 (15) | −0.0070 (10) | −0.0085 (11) | −0.0049 (11) |
C42 | 0.0603 (16) | 0.0421 (13) | 0.0485 (14) | −0.0038 (11) | −0.0213 (12) | −0.0005 (11) |
C29 | 0.0508 (15) | 0.0493 (16) | 0.0590 (15) | −0.0145 (11) | −0.0112 (12) | −0.0076 (12) |
C31 | 0.0512 (15) | 0.0418 (13) | 0.0524 (14) | −0.0096 (10) | −0.0069 (12) | 0.0047 (11) |
C41 | 0.0724 (19) | 0.0532 (15) | 0.0485 (14) | 0.0038 (13) | −0.0090 (13) | −0.0042 (11) |
C5 | 0.0380 (14) | 0.0608 (18) | 0.092 (2) | −0.0133 (12) | −0.0069 (14) | −0.0085 (16) |
O1 | 0.1099 (18) | 0.0655 (13) | 0.0787 (15) | −0.0053 (12) | 0.0197 (13) | −0.0025 (11) |
O2 | 0.0701 (14) | 0.0613 (12) | 0.1211 (18) | −0.0184 (10) | 0.0067 (12) | 0.0114 (12) |
C30 | 0.0575 (15) | 0.0558 (15) | 0.0528 (14) | −0.0174 (12) | −0.0069 (12) | 0.0029 (12) |
C10 | 0.0591 (17) | 0.0497 (15) | 0.0562 (15) | 0.0016 (12) | 0.0018 (12) | −0.0111 (12) |
C16 | 0.0520 (16) | 0.0478 (15) | 0.0802 (18) | −0.0153 (12) | 0.0007 (13) | −0.0177 (13) |
N1 | 0.0558 (14) | 0.0536 (14) | 0.0845 (17) | −0.0089 (10) | 0.0041 (12) | −0.0108 (12) |
C25 | 0.0572 (16) | 0.0581 (16) | 0.0578 (15) | −0.0057 (12) | 0.0004 (12) | −0.0115 (12) |
C21 | 0.0587 (18) | 0.0454 (15) | 0.092 (2) | −0.0123 (13) | 0.0007 (15) | −0.0161 (14) |
C38 | 0.0582 (16) | 0.0567 (15) | 0.0610 (16) | −0.0092 (12) | −0.0134 (13) | −0.0141 (12) |
C8 | 0.0509 (17) | 0.0581 (18) | 0.088 (2) | −0.0095 (13) | 0.0134 (15) | −0.0064 (16) |
C40 | 0.0599 (17) | 0.0609 (17) | 0.0768 (19) | −0.0066 (14) | 0.0011 (14) | 0.0045 (15) |
C7 | 0.0474 (15) | 0.0502 (15) | 0.093 (2) | −0.0155 (12) | 0.0027 (14) | −0.0117 (15) |
C22 | 0.0614 (17) | 0.0571 (17) | 0.0697 (17) | −0.0020 (13) | −0.0109 (14) | 0.0022 (14) |
C24 | 0.0649 (18) | 0.0572 (17) | 0.079 (2) | 0.0022 (13) | 0.0011 (15) | −0.0188 (15) |
C11 | 0.0670 (18) | 0.0516 (16) | 0.088 (2) | 0.0033 (13) | −0.0225 (16) | −0.0061 (14) |
C17 | 0.0569 (18) | 0.0725 (19) | 0.0762 (19) | −0.0184 (15) | −0.0010 (15) | −0.0185 (15) |
C6 | 0.0453 (15) | 0.0583 (17) | 0.088 (2) | −0.0143 (12) | −0.0031 (14) | −0.0142 (15) |
C39 | 0.0580 (17) | 0.0588 (17) | 0.086 (2) | −0.0161 (13) | −0.0110 (15) | −0.0076 (15) |
C13 | 0.073 (2) | 0.075 (2) | 0.0657 (17) | −0.0189 (16) | −0.0169 (15) | −0.0033 (15) |
C18 | 0.0542 (19) | 0.091 (2) | 0.092 (2) | −0.0155 (17) | 0.0013 (16) | −0.031 (2) |
C1 | 0.0603 (19) | 0.071 (2) | 0.103 (3) | −0.0149 (15) | −0.0110 (17) | −0.0228 (19) |
C36 | 0.073 (2) | 0.079 (2) | 0.0649 (18) | 0.0019 (15) | −0.0204 (15) | −0.0119 (15) |
C2 | 0.074 (2) | 0.106 (3) | 0.089 (2) | −0.0201 (19) | −0.0206 (18) | −0.012 (2) |
C20 | 0.077 (2) | 0.0543 (17) | 0.102 (2) | −0.0088 (15) | −0.0115 (18) | −0.0159 (16) |
C23 | 0.0681 (19) | 0.0467 (16) | 0.097 (2) | 0.0043 (13) | −0.0051 (16) | −0.0072 (16) |
C4 | 0.0515 (17) | 0.0682 (19) | 0.099 (2) | −0.0089 (14) | −0.0147 (16) | −0.0056 (18) |
C9 | 0.0577 (17) | 0.0554 (16) | 0.090 (2) | −0.0020 (13) | 0.0099 (15) | −0.0146 (15) |
C3 | 0.063 (2) | 0.091 (3) | 0.101 (3) | −0.0152 (17) | −0.0232 (18) | 0.001 (2) |
C19 | 0.061 (2) | 0.080 (2) | 0.111 (3) | 0.0014 (16) | −0.0157 (19) | −0.033 (2) |
C32 | 0.0594 (19) | 0.088 (2) | 0.0713 (19) | −0.0060 (15) | 0.0015 (15) | 0.0098 (16) |
C15 | 0.081 (2) | 0.0563 (16) | 0.0761 (19) | −0.0048 (15) | −0.0175 (16) | 0.0079 (14) |
C12 | 0.093 (2) | 0.0561 (17) | 0.092 (2) | −0.0187 (16) | −0.0321 (19) | 0.0075 (16) |
C14 | 0.074 (2) | 0.082 (2) | 0.0760 (19) | −0.0005 (16) | −0.0275 (16) | 0.0025 (16) |
C35 | 0.118 (3) | 0.083 (2) | 0.106 (3) | −0.001 (2) | −0.063 (3) | −0.015 (2) |
C33 | 0.050 (2) | 0.110 (3) | 0.132 (3) | −0.0178 (18) | −0.008 (2) | 0.042 (3) |
C34 | 0.095 (3) | 0.076 (2) | 0.160 (4) | −0.031 (2) | −0.070 (3) | 0.031 (3) |
O4—C42 | 1.361 (3) | C40—H40 | 0.9300 |
O4—H4 | 0.8200 | C7—C6 | 1.483 (4) |
N2—C29 | 1.355 (3) | C7—H7 | 0.9800 |
N2—C26 | 1.411 (3) | C22—C23 | 1.390 (4) |
N2—C30 | 1.456 (3) | C22—H22 | 0.9300 |
O3—C29 | 1.226 (3) | C24—C23 | 1.371 (4) |
C26—C25 | 1.374 (3) | C24—H24 | 0.9300 |
C26—C27 | 1.382 (3) | C11—C12 | 1.379 (4) |
C37—C38 | 1.377 (3) | C11—H11 | 0.9300 |
C37—C42 | 1.390 (3) | C17—C18 | 1.385 (4) |
C37—C28 | 1.518 (3) | C17—H17 | 0.9300 |
C28—C27 | 1.502 (3) | C6—C1 | 1.389 (4) |
C28—C29 | 1.532 (3) | C39—H39 | 0.9300 |
C28—H28 | 0.9800 | C13—C14 | 1.364 (4) |
C27—C22 | 1.379 (3) | C13—C12 | 1.368 (4) |
C42—C41 | 1.385 (4) | C13—H13 | 0.9300 |
C31—C36 | 1.367 (4) | C18—C19 | 1.359 (5) |
C31—C32 | 1.377 (4) | C18—H18 | 0.9300 |
C31—C30 | 1.497 (3) | C1—C2 | 1.379 (5) |
C41—C40 | 1.375 (4) | C1—H1 | 0.9300 |
C41—H41 | 0.9300 | C36—C35 | 1.362 (5) |
C5—C4 | 1.366 (4) | C36—H36 | 0.9300 |
C5—C6 | 1.392 (4) | C2—C3 | 1.379 (5) |
C5—N1 | 1.401 (4) | C2—H2A | 0.9300 |
O1—C8 | 1.220 (4) | C20—C19 | 1.375 (4) |
O2—C21 | 1.364 (3) | C20—H20 | 0.9300 |
O2—H2 | 0.8200 | C23—H23 | 0.9300 |
C30—H30A | 0.9700 | C4—C3 | 1.378 (5) |
C30—H30B | 0.9700 | C4—H4A | 0.9300 |
C10—C11 | 1.367 (4) | C9—H9A | 0.9700 |
C10—C15 | 1.372 (4) | C9—H9B | 0.9700 |
C10—C9 | 1.508 (4) | C3—H3 | 0.9300 |
C16—C17 | 1.384 (4) | C19—H19 | 0.9300 |
C16—C21 | 1.386 (4) | C32—C33 | 1.381 (5) |
C16—C7 | 1.514 (4) | C32—H32 | 0.9300 |
N1—C8 | 1.362 (4) | C15—C14 | 1.368 (4) |
N1—C9 | 1.452 (4) | C15—H15 | 0.9300 |
C25—C24 | 1.382 (4) | C12—H12 | 0.9300 |
C25—H25 | 0.9300 | C14—H14 | 0.9300 |
C21—C20 | 1.373 (4) | C35—C34 | 1.346 (6) |
C38—C39 | 1.374 (4) | C35—H35 | 0.9300 |
C38—H38 | 0.9300 | C33—C34 | 1.363 (6) |
C8—C7 | 1.533 (4) | C33—H33 | 0.9300 |
C40—C39 | 1.365 (4) | C34—H34 | 0.9300 |
C42—O4—H4 | 109.5 | C23—C22—H22 | 120.6 |
C29—N2—C26 | 111.12 (19) | C23—C24—C25 | 121.0 (3) |
C29—N2—C30 | 124.0 (2) | C23—C24—H24 | 119.5 |
C26—N2—C30 | 124.8 (2) | C25—C24—H24 | 119.5 |
C25—C26—C27 | 122.7 (2) | C10—C11—C12 | 121.5 (3) |
C25—C26—N2 | 128.2 (2) | C10—C11—H11 | 119.3 |
C27—C26—N2 | 109.1 (2) | C12—C11—H11 | 119.3 |
C38—C37—C42 | 118.4 (2) | C18—C17—C16 | 120.9 (3) |
C38—C37—C28 | 121.5 (2) | C18—C17—H17 | 119.6 |
C42—C37—C28 | 120.2 (2) | C16—C17—H17 | 119.6 |
C27—C28—C37 | 114.06 (18) | C1—C6—C5 | 118.6 (3) |
C27—C28—C29 | 101.62 (19) | C1—C6—C7 | 132.1 (3) |
C37—C28—C29 | 110.23 (19) | C5—C6—C7 | 109.3 (3) |
C27—C28—H28 | 110.2 | C40—C39—C38 | 119.0 (2) |
C37—C28—H28 | 110.2 | C40—C39—H39 | 120.5 |
C29—C28—H28 | 110.2 | C38—C39—H39 | 120.5 |
C22—C27—C26 | 119.3 (2) | C14—C13—C12 | 119.4 (3) |
C22—C27—C28 | 131.1 (2) | C14—C13—H13 | 120.3 |
C26—C27—C28 | 109.5 (2) | C12—C13—H13 | 120.3 |
O4—C42—C41 | 122.4 (2) | C19—C18—C17 | 119.4 (3) |
O4—C42—C37 | 117.8 (2) | C19—C18—H18 | 120.3 |
C41—C42—C37 | 119.8 (2) | C17—C18—H18 | 120.3 |
O3—C29—N2 | 123.7 (2) | C2—C1—C6 | 119.1 (3) |
O3—C29—C28 | 127.8 (2) | C2—C1—H1 | 120.4 |
N2—C29—C28 | 108.5 (2) | C6—C1—H1 | 120.4 |
C36—C31—C32 | 117.9 (3) | C35—C36—C31 | 121.5 (3) |
C36—C31—C30 | 121.1 (2) | C35—C36—H36 | 119.2 |
C32—C31—C30 | 120.9 (2) | C31—C36—H36 | 119.2 |
C40—C41—C42 | 120.2 (3) | C3—C2—C1 | 121.1 (3) |
C40—C41—H41 | 119.9 | C3—C2—H2A | 119.5 |
C42—C41—H41 | 119.9 | C1—C2—H2A | 119.5 |
C4—C5—C6 | 122.4 (3) | C21—C20—C19 | 119.9 (3) |
C4—C5—N1 | 128.6 (3) | C21—C20—H20 | 120.1 |
C6—C5—N1 | 109.0 (3) | C19—C20—H20 | 120.1 |
C21—O2—H2 | 109.5 | C24—C23—C22 | 120.9 (3) |
N2—C30—C31 | 113.23 (18) | C24—C23—H23 | 119.5 |
N2—C30—H30A | 108.9 | C22—C23—H23 | 119.5 |
C31—C30—H30A | 108.9 | C5—C4—C3 | 118.4 (3) |
N2—C30—H30B | 108.9 | C5—C4—H4A | 120.8 |
C31—C30—H30B | 108.9 | C3—C4—H4A | 120.8 |
H30A—C30—H30B | 107.7 | N1—C9—C10 | 111.9 (2) |
C11—C10—C15 | 117.7 (3) | N1—C9—H9A | 109.2 |
C11—C10—C9 | 122.2 (3) | C10—C9—H9A | 109.2 |
C15—C10—C9 | 120.1 (3) | N1—C9—H9B | 109.2 |
C17—C16—C21 | 118.5 (3) | C10—C9—H9B | 109.2 |
C17—C16—C7 | 121.6 (3) | H9A—C9—H9B | 107.9 |
C21—C16—C7 | 119.9 (2) | C4—C3—C2 | 120.5 (3) |
C8—N1—C5 | 111.4 (2) | C4—C3—H3 | 119.8 |
C8—N1—C9 | 122.9 (3) | C2—C3—H3 | 119.8 |
C5—N1—C9 | 125.1 (2) | C18—C19—C20 | 120.8 (3) |
C26—C25—C24 | 117.4 (2) | C18—C19—H19 | 119.6 |
C26—C25—H25 | 121.3 | C20—C19—H19 | 119.6 |
C24—C25—H25 | 121.3 | C31—C32—C33 | 120.2 (3) |
O2—C21—C20 | 122.5 (3) | C31—C32—H32 | 119.9 |
O2—C21—C16 | 117.0 (3) | C33—C32—H32 | 119.9 |
C20—C21—C16 | 120.5 (3) | C14—C15—C10 | 121.5 (3) |
C39—C38—C37 | 122.0 (2) | C14—C15—H15 | 119.3 |
C39—C38—H38 | 119.0 | C10—C15—H15 | 119.3 |
C37—C38—H38 | 119.0 | C13—C12—C11 | 119.7 (3) |
O1—C8—N1 | 123.5 (3) | C13—C12—H12 | 120.1 |
O1—C8—C7 | 128.8 (3) | C11—C12—H12 | 120.1 |
N1—C8—C7 | 107.6 (3) | C13—C14—C15 | 120.2 (3) |
C39—C40—C41 | 120.6 (3) | C13—C14—H14 | 119.9 |
C39—C40—H40 | 119.7 | C15—C14—H14 | 119.9 |
C41—C40—H40 | 119.7 | C34—C35—C36 | 120.4 (4) |
C6—C7—C16 | 118.5 (2) | C34—C35—H35 | 119.8 |
C6—C7—C8 | 102.5 (2) | C36—C35—H35 | 119.8 |
C16—C7—C8 | 112.2 (2) | C34—C33—C32 | 120.2 (3) |
C6—C7—H7 | 107.7 | C34—C33—H33 | 119.9 |
C16—C7—H7 | 107.7 | C32—C33—H33 | 119.9 |
C8—C7—H7 | 107.7 | C35—C34—C33 | 119.8 (3) |
C27—C22—C23 | 118.7 (3) | C35—C34—H34 | 120.1 |
C27—C22—H22 | 120.6 | C33—C34—H34 | 120.1 |
C29—N2—C26—C25 | −178.9 (2) | C21—C16—C7—C8 | −82.0 (3) |
C30—N2—C26—C25 | 0.5 (4) | O1—C8—C7—C6 | 175.7 (3) |
C29—N2—C26—C27 | 0.5 (3) | N1—C8—C7—C6 | −3.4 (3) |
C30—N2—C26—C27 | 179.8 (2) | O1—C8—C7—C16 | 47.4 (4) |
C38—C37—C28—C27 | 22.5 (3) | N1—C8—C7—C16 | −131.7 (2) |
C42—C37—C28—C27 | −159.4 (2) | C26—C27—C22—C23 | −0.3 (4) |
C38—C37—C28—C29 | −91.0 (3) | C28—C27—C22—C23 | −175.8 (2) |
C42—C37—C28—C29 | 87.0 (2) | C26—C25—C24—C23 | 0.4 (4) |
C25—C26—C27—C22 | 0.0 (4) | C15—C10—C11—C12 | 1.4 (4) |
N2—C26—C27—C22 | −179.4 (2) | C9—C10—C11—C12 | −177.7 (3) |
C25—C26—C27—C28 | 176.4 (2) | C21—C16—C17—C18 | 0.9 (4) |
N2—C26—C27—C28 | −3.0 (3) | C7—C16—C17—C18 | −177.5 (3) |
C37—C28—C27—C22 | 61.3 (3) | C4—C5—C6—C1 | −0.6 (4) |
C29—C28—C27—C22 | 179.9 (2) | N1—C5—C6—C1 | 180.0 (2) |
C37—C28—C27—C26 | −114.6 (2) | C4—C5—C6—C7 | 177.6 (2) |
C29—C28—C27—C26 | 4.0 (2) | N1—C5—C6—C7 | −1.8 (3) |
C38—C37—C42—O4 | −179.0 (2) | C16—C7—C6—C1 | −54.8 (4) |
C28—C37—C42—O4 | 2.9 (3) | C8—C7—C6—C1 | −179.0 (3) |
C38—C37—C42—C41 | 0.6 (3) | C16—C7—C6—C5 | 127.3 (2) |
C28—C37—C42—C41 | −177.5 (2) | C8—C7—C6—C5 | 3.1 (3) |
C26—N2—C29—O3 | −179.0 (2) | C41—C40—C39—C38 | 0.0 (4) |
C30—N2—C29—O3 | 1.6 (4) | C37—C38—C39—C40 | 0.1 (4) |
C26—N2—C29—C28 | 2.1 (2) | C16—C17—C18—C19 | 0.8 (4) |
C30—N2—C29—C28 | −177.21 (19) | C5—C6—C1—C2 | 1.0 (4) |
C27—C28—C29—O3 | 177.6 (2) | C7—C6—C1—C2 | −176.7 (3) |
C37—C28—C29—O3 | −61.2 (3) | C32—C31—C36—C35 | −0.2 (4) |
C27—C28—C29—N2 | −3.7 (2) | C30—C31—C36—C35 | 178.0 (3) |
C37—C28—C29—N2 | 117.6 (2) | C6—C1—C2—C3 | −0.5 (5) |
O4—C42—C41—C40 | 179.1 (2) | O2—C21—C20—C19 | −177.6 (3) |
C37—C42—C41—C40 | −0.5 (3) | C16—C21—C20—C19 | 2.1 (4) |
C29—N2—C30—C31 | 105.8 (3) | C25—C24—C23—C22 | −0.7 (4) |
C26—N2—C30—C31 | −73.5 (3) | C27—C22—C23—C24 | 0.6 (4) |
C36—C31—C30—N2 | 124.5 (3) | C6—C5—C4—C3 | −0.4 (4) |
C32—C31—C30—N2 | −57.3 (3) | N1—C5—C4—C3 | 178.9 (3) |
C4—C5—N1—C8 | −179.9 (2) | C8—N1—C9—C10 | −95.5 (3) |
C6—C5—N1—C8 | −0.5 (3) | C5—N1—C9—C10 | 75.2 (3) |
C4—C5—N1—C9 | 8.5 (4) | C11—C10—C9—N1 | −120.7 (3) |
C6—C5—N1—C9 | −172.2 (2) | C15—C10—C9—N1 | 60.2 (4) |
C27—C26—C25—C24 | 0.0 (4) | C5—C4—C3—C2 | 0.9 (4) |
N2—C26—C25—C24 | 179.2 (2) | C1—C2—C3—C4 | −0.5 (5) |
C17—C16—C21—O2 | 177.4 (2) | C17—C18—C19—C20 | −1.1 (5) |
C7—C16—C21—O2 | −4.2 (4) | C21—C20—C19—C18 | −0.3 (5) |
C17—C16—C21—C20 | −2.3 (4) | C36—C31—C32—C33 | −0.3 (4) |
C7—C16—C21—C20 | 176.1 (3) | C30—C31—C32—C33 | −178.5 (2) |
C42—C37—C38—C39 | −0.4 (4) | C11—C10—C15—C14 | −0.8 (4) |
C28—C37—C38—C39 | 177.7 (2) | C9—C10—C15—C14 | 178.3 (3) |
C5—N1—C8—O1 | −176.6 (3) | C14—C13—C12—C11 | −0.1 (5) |
C9—N1—C8—O1 | −4.7 (4) | C10—C11—C12—C13 | −1.0 (5) |
C5—N1—C8—C7 | 2.6 (3) | C12—C13—C14—C15 | 0.8 (5) |
C9—N1—C8—C7 | 174.4 (2) | C10—C15—C14—C13 | −0.3 (5) |
C42—C41—C40—C39 | 0.2 (4) | C31—C36—C35—C34 | 0.3 (5) |
C17—C16—C7—C6 | −22.9 (4) | C31—C32—C33—C34 | 0.6 (5) |
C21—C16—C7—C6 | 158.8 (2) | C36—C35—C34—C33 | 0.0 (5) |
C17—C16—C7—C8 | 96.4 (3) | C32—C33—C34—C35 | −0.5 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 0.82 | 1.93 | 2.721 (3) | 160 |
O4—H4···O3ii | 0.82 | 1.95 | 2.735 (3) | 160 |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x+1, −y+1, −z+1. |
Acknowledgements
The authors thank the single-crystal XRD facility, SAIF IIT Madras, Chennai, for the data collection.
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