organic compounds
5′-Benzylidene-1′′-methyl-4′′-phenyltrispiro[1,3-dioxolane-2,1′-cyclohexane-3′,3′′-pyrrolidine-2′′,3′′′-indole]-4′,2′′′-dione
aDepartment of Physics, S. D. N. B. Vaishnav College for Women, Chromepet, Chennai 600 004, India, bSchool of Basic Sciences, Vels University, Pallavaram, Chennai, India, and cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
*Correspondence e-mail: lakssdnbvc@gmail.com
In the title compound, C32H30N2O4, two spiro links connect the methyl-substituted pyrrolidine ring to the oxindole and cyclohexanone rings. The cyclohexanone ring is further connected to the dioxalane ring by a third spiro junction. Both the pyrrolidine and dioxalane rings adopt a twist conformation. The indole ring is nearly planar, with a maximum deviation of 0.0296 (7) Å, and the cyclohexanone ring adopts a distorted boat conformation. In the crystal, C—H⋯O and N—H⋯N hydrogen-bonding interactions connect molecules into chains running parallel to the b axis, which are further linked into layers parallel to the ab plane by C—H⋯O hydrogen bonds.
Keywords: crystal structure; trispiropyrrolidine; spirooxindole; dioxalane.
CCDC reference: 1546766
Structure description
et al., 1991) and possess anticancer (Chin et al., 2008), antibacterial (Sar et al., 2006), antioxidant (Sarma et al., 2010) and anticonvulsant activities (Obniska & Kamiński, 2006). Some act as pain-relief agents (Frank et al., 2008) and pesticides (Wei et al., 2009). Spiro pyrrolidine derivatives exhibit antimicrobial and neurotoxic properties (Obniska et al., 2006). Oxindole derivatives are found to have antimicrobial (Karki et al., 2011) and antioxidant (Rindhe et al., 2011) properties. Spirooxindole derivatives act as inhibitors of human NK-1 receptor. containing a spiroindolepyrrolidine nucleus are found to be useful in cancer chemotherapy (Fischer et al., 2000). Spiropyrrolidine compounds containing oxindole and cyclohexanone ring systems are found to have antimicrobial and antifungal activities (Raj et al., 2003). Dioxalane moieties play a significant role in stabilizing mutant HIV-1 RT and nucleoside triphosphate and act as nucleoside reverse transcriptase inhibitors (NRTIs) (Liang et al., 2006).
are present in many natural products (JamesIn the title compound (Fig. 1) the methyl-substituted pyrrolidine ring (N1/C10/C16/C17/C8) and the dioxalane ring (O3/O2/C12/C14/C15) both adopt a twist conformation with puckering parameters q2 = 0.480 (8) Å, φ2 = 313.34 (6)° and q2 = 0.221 (9) Å, φ2 = 350.46 (3)°, respectively. The six-membered cyclohexanone ring (C8–C13) adopts a distorted boat conformation [QT = 0.666 (2) Å, θ = 99.42 (16)°, φ = 71.38 (7)°]. The pyrrolidine ring mean plane forms dihedral angles of 58.10 (1) and 87.45 (9)°, respectively, with the mean planes of the benzene ring and the mean plane of the cyclohexanone rings The cyclohexanone ring makes a dihedral angle of 84.14 (1)° with the mean plane of the dioxalane ring. The indole ring (C21–C26/N2/C19/C20) is nearly planar with a maximum deviation of 0.0296 (7) Å for atom C23. An intramolecular C—H⋯O hydrogen bond occurs. The geometrical parameters of the title compound are in good agreement with those previously reported for trispiropyrrolidine compounds (Chandralekha et al., 2015, 2016).
In the crystal, molecules are linked by weak C—H⋯O and N—H⋯O interactions (Table 1), forming chains extending along the b-axis direction (Fig. 2). The chains are further linked into layers parallel to the ab plane by C—H⋯O hydrogen bonds.
Synthesis and crystallization
An equimolar mixture of 7,9-bis[(E)-benzylidine)]-1,4-dioxospiro[4,5]decane-8-one (1 mmol), isatin (1 mmol) and sarcosine (1 mmol) in methanol (25–30 ml) was refluxed for 3 h. After the completion of the reaction as indicated by TLC, the crude product was purified by using a mixture of petroleum ether and ethylacetate (8:2 v/v). Crystals of the title compound were obtained by the slow evaporation of a methanol solution at room temperature.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1546766
https://doi.org/10.1107/S2414314617006393/rz4014sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617006393/rz4014Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617006393/rz4014Isup3.cml
Data collection: APEX2 (Bruker, 2008); cell
APEX2 (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).C32H30N2O4 | F(000) = 1072 |
Mr = 506.58 | Dx = 1.303 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 13.9601 (2) Å | Cell parameters from 6394 reflections |
b = 11.1172 (2) Å | θ = 1.8–28.4° |
c = 16.7313 (3) Å | µ = 0.09 mm−1 |
β = 96.019 (1)° | T = 296 K |
V = 2582.34 (8) Å3 | Block, colorless |
Z = 4 | 0.23 × 0.15 × 0.11 mm |
Bruker SMART APEXII area-detector diffractometer | 3887 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.029 |
ω and φ scans | θmax = 28.4°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −18→14 |
Tmin = 0.744, Tmax = 0.859 | k = −14→14 |
24317 measured reflections | l = −22→22 |
6395 independent reflections |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.045 | w = 1/[σ2(Fo2) + (0.0534P)2 + 0.3939P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.130 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.18 e Å−3 |
6395 reflections | Δρmin = −0.19 e Å−3 |
349 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0017 (6) |
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. The N-bound indole H atom was located in a difference Fourier map and refined freely. All other H atoms were placed geometrically and refined using a riding atom approximation, with C–H = 0.93–0.97 \%A, and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C) for methyl H atoms. A rotating model was used for the methyl group. |
x | y | z | Uiso*/Ueq | ||
H34 | 0.2804 (14) | −0.0171 (18) | 0.2545 (12) | 0.075 (6)* | |
O1 | 0.55773 (8) | 0.20767 (10) | 0.13693 (6) | 0.0542 (3) | |
O2 | 0.60579 (9) | 0.38736 (11) | 0.31054 (7) | 0.0640 (3) | |
O3 | 0.50902 (10) | 0.40585 (12) | 0.41115 (7) | 0.0714 (4) | |
O4 | 0.27663 (10) | 0.19821 (11) | 0.30938 (8) | 0.0711 (4) | |
N1 | 0.26684 (9) | 0.33561 (12) | 0.15637 (9) | 0.0563 (4) | |
N2 | 0.30089 (10) | 0.04319 (13) | 0.22479 (9) | 0.0539 (3) | |
C1 | 0.56550 (15) | −0.05286 (18) | 0.39691 (13) | 0.0785 (6) | |
H1 | 0.5130 | −0.0036 | 0.4033 | 0.094* | |
C2 | 0.5949 (2) | −0.1353 (2) | 0.45585 (15) | 0.1011 (8) | |
H2 | 0.5617 | −0.1414 | 0.5010 | 0.121* | |
C3 | 0.67203 (17) | −0.2077 (2) | 0.44884 (15) | 0.0856 (6) | |
H3 | 0.6933 | −0.2607 | 0.4899 | 0.103* | |
C4 | 0.71750 (14) | −0.20157 (17) | 0.38123 (15) | 0.0763 (6) | |
H4 | 0.7690 | −0.2526 | 0.3751 | 0.092* | |
C5 | 0.68774 (13) | −0.12001 (16) | 0.32126 (12) | 0.0647 (5) | |
H5 | 0.7191 | −0.1176 | 0.2749 | 0.078* | |
C6 | 0.61193 (11) | −0.04194 (14) | 0.32915 (10) | 0.0529 (4) | |
C7 | 0.58309 (11) | 0.04513 (14) | 0.26516 (10) | 0.0510 (4) | |
H7 | 0.5944 | 0.0223 | 0.2135 | 0.061* | |
C8 | 0.54258 (11) | 0.15314 (13) | 0.27172 (9) | 0.0462 (4) | |
C9 | 0.51663 (10) | 0.22333 (13) | 0.19660 (9) | 0.0431 (3) | |
C10 | 0.43116 (11) | 0.31046 (13) | 0.19660 (9) | 0.0439 (3) | |
C11 | 0.43230 (12) | 0.37857 (14) | 0.27751 (9) | 0.0499 (4) | |
H11A | 0.4331 | 0.4644 | 0.2671 | 0.060* | |
H11B | 0.3735 | 0.3603 | 0.3012 | 0.060* | |
C12 | 0.51770 (12) | 0.34690 (15) | 0.33712 (9) | 0.0537 (4) | |
C13 | 0.52437 (13) | 0.21313 (14) | 0.34906 (10) | 0.0560 (4) | |
H13A | 0.5763 | 0.1945 | 0.3903 | 0.067* | |
H13B | 0.4648 | 0.1832 | 0.3666 | 0.067* | |
C14 | 0.62840 (17) | 0.4986 (2) | 0.34848 (13) | 0.0810 (6) | |
H14A | 0.6055 | 0.5650 | 0.3140 | 0.097* | |
H14B | 0.6974 | 0.5068 | 0.3619 | 0.097* | |
C15 | 0.5784 (2) | 0.4959 (3) | 0.42173 (17) | 0.1216 (11) | |
H15A | 0.6237 | 0.4787 | 0.4683 | 0.146* | |
H15B | 0.5483 | 0.5730 | 0.4298 | 0.146* | |
C16 | 0.42296 (11) | 0.39768 (13) | 0.12265 (9) | 0.0477 (4) | |
H16 | 0.4426 | 0.3513 | 0.0773 | 0.057* | |
C17 | 0.31406 (12) | 0.41924 (16) | 0.10477 (11) | 0.0585 (4) | |
H17A | 0.2982 | 0.5018 | 0.1169 | 0.070* | |
H17B | 0.2933 | 0.4036 | 0.0486 | 0.070* | |
C18 | 0.17083 (14) | 0.2983 (2) | 0.12196 (15) | 0.0858 (6) | |
H18A | 0.1756 | 0.2573 | 0.0720 | 0.129* | |
H18B | 0.1305 | 0.3678 | 0.1126 | 0.129* | |
H18C | 0.1434 | 0.2451 | 0.1587 | 0.129* | |
C19 | 0.33456 (11) | 0.23636 (14) | 0.17605 (9) | 0.0478 (4) | |
C20 | 0.30084 (11) | 0.16007 (15) | 0.24632 (10) | 0.0527 (4) | |
C21 | 0.32460 (11) | 0.02762 (14) | 0.14589 (9) | 0.0478 (4) | |
C22 | 0.33136 (13) | −0.07893 (15) | 0.10525 (11) | 0.0602 (4) | |
H22 | 0.3184 | −0.1521 | 0.1288 | 0.072* | |
C23 | 0.35801 (13) | −0.07359 (16) | 0.02831 (11) | 0.0633 (5) | |
H23 | 0.3651 | −0.1444 | 0.0000 | 0.076* | |
C24 | 0.37418 (13) | 0.03456 (17) | −0.00690 (10) | 0.0619 (5) | |
H24 | 0.3911 | 0.0363 | −0.0592 | 0.074* | |
C25 | 0.36575 (13) | 0.14113 (16) | 0.03418 (10) | 0.0578 (4) | |
H25 | 0.3757 | 0.2142 | 0.0093 | 0.069* | |
C26 | 0.34236 (11) | 0.13880 (14) | 0.11277 (9) | 0.0472 (4) | |
C27 | 0.48698 (12) | 0.50767 (14) | 0.13050 (9) | 0.0513 (4) | |
C28 | 0.57991 (13) | 0.49828 (17) | 0.10901 (11) | 0.0620 (5) | |
H28 | 0.5999 | 0.4264 | 0.0877 | 0.074* | |
C29 | 0.64358 (15) | 0.5941 (2) | 0.11874 (12) | 0.0752 (6) | |
H29 | 0.7059 | 0.5856 | 0.1047 | 0.090* | |
C30 | 0.61510 (18) | 0.70108 (19) | 0.14885 (13) | 0.0801 (6) | |
H30 | 0.6579 | 0.7652 | 0.1557 | 0.096* | |
C31 | 0.52327 (18) | 0.71291 (18) | 0.16884 (13) | 0.0813 (6) | |
H31 | 0.5035 | 0.7858 | 0.1888 | 0.098* | |
C32 | 0.45946 (15) | 0.61805 (16) | 0.15977 (12) | 0.0674 (5) | |
H32 | 0.3971 | 0.6280 | 0.1734 | 0.081* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0603 (7) | 0.0571 (7) | 0.0482 (6) | 0.0074 (5) | 0.0201 (5) | −0.0006 (5) |
O2 | 0.0668 (8) | 0.0686 (8) | 0.0587 (7) | −0.0144 (6) | 0.0169 (6) | −0.0134 (6) |
O3 | 0.0961 (10) | 0.0747 (8) | 0.0465 (7) | −0.0110 (7) | 0.0218 (6) | −0.0175 (6) |
O4 | 0.0849 (9) | 0.0665 (8) | 0.0694 (8) | −0.0102 (6) | 0.0441 (7) | −0.0104 (6) |
N1 | 0.0473 (8) | 0.0520 (8) | 0.0710 (9) | 0.0041 (6) | 0.0122 (7) | 0.0024 (7) |
N2 | 0.0617 (8) | 0.0473 (8) | 0.0562 (8) | −0.0055 (6) | 0.0232 (7) | 0.0015 (6) |
C1 | 0.0779 (13) | 0.0704 (12) | 0.0926 (15) | 0.0236 (10) | 0.0340 (11) | 0.0289 (11) |
C2 | 0.125 (2) | 0.0888 (16) | 0.0965 (17) | 0.0344 (15) | 0.0462 (15) | 0.0448 (13) |
C3 | 0.0870 (15) | 0.0738 (14) | 0.0952 (16) | 0.0150 (11) | 0.0054 (13) | 0.0334 (12) |
C4 | 0.0584 (11) | 0.0577 (11) | 0.1112 (17) | 0.0115 (9) | 0.0019 (11) | 0.0116 (11) |
C5 | 0.0608 (11) | 0.0547 (10) | 0.0798 (13) | 0.0059 (8) | 0.0131 (9) | 0.0003 (9) |
C6 | 0.0486 (9) | 0.0457 (9) | 0.0642 (10) | 0.0006 (7) | 0.0048 (8) | 0.0056 (7) |
C7 | 0.0488 (9) | 0.0500 (9) | 0.0546 (9) | 0.0010 (7) | 0.0076 (7) | 0.0013 (7) |
C8 | 0.0473 (8) | 0.0463 (9) | 0.0459 (8) | −0.0016 (7) | 0.0097 (7) | 0.0028 (7) |
C9 | 0.0476 (8) | 0.0397 (8) | 0.0435 (8) | −0.0018 (6) | 0.0113 (7) | −0.0023 (6) |
C10 | 0.0500 (8) | 0.0405 (8) | 0.0432 (8) | 0.0011 (6) | 0.0139 (7) | 0.0009 (6) |
C11 | 0.0624 (10) | 0.0414 (8) | 0.0488 (9) | 0.0006 (7) | 0.0191 (7) | −0.0027 (7) |
C12 | 0.0666 (10) | 0.0566 (10) | 0.0404 (8) | −0.0044 (8) | 0.0173 (7) | −0.0059 (7) |
C13 | 0.0693 (11) | 0.0558 (10) | 0.0441 (9) | 0.0043 (8) | 0.0119 (8) | 0.0047 (7) |
C14 | 0.0905 (15) | 0.0779 (13) | 0.0751 (13) | −0.0227 (11) | 0.0114 (11) | −0.0172 (11) |
C15 | 0.156 (3) | 0.120 (2) | 0.0979 (19) | −0.0632 (19) | 0.0531 (18) | −0.0549 (16) |
C16 | 0.0562 (9) | 0.0433 (8) | 0.0450 (8) | 0.0043 (7) | 0.0120 (7) | 0.0023 (6) |
C17 | 0.0593 (10) | 0.0574 (10) | 0.0589 (10) | 0.0069 (8) | 0.0072 (8) | 0.0074 (8) |
C18 | 0.0533 (11) | 0.0822 (14) | 0.1205 (19) | 0.0042 (10) | 0.0019 (11) | 0.0063 (13) |
C19 | 0.0497 (9) | 0.0455 (8) | 0.0504 (9) | 0.0013 (7) | 0.0155 (7) | −0.0006 (7) |
C20 | 0.0496 (9) | 0.0541 (10) | 0.0577 (10) | −0.0018 (7) | 0.0213 (8) | −0.0009 (8) |
C21 | 0.0452 (8) | 0.0493 (9) | 0.0503 (9) | −0.0027 (7) | 0.0117 (7) | −0.0012 (7) |
C22 | 0.0674 (11) | 0.0469 (9) | 0.0683 (11) | −0.0082 (8) | 0.0175 (9) | −0.0052 (8) |
C23 | 0.0685 (11) | 0.0583 (11) | 0.0646 (11) | −0.0092 (9) | 0.0143 (9) | −0.0183 (9) |
C24 | 0.0699 (11) | 0.0695 (12) | 0.0473 (9) | −0.0115 (9) | 0.0113 (8) | −0.0110 (8) |
C25 | 0.0724 (11) | 0.0552 (10) | 0.0464 (9) | −0.0079 (8) | 0.0082 (8) | −0.0003 (8) |
C26 | 0.0468 (8) | 0.0480 (9) | 0.0476 (9) | −0.0030 (7) | 0.0086 (7) | −0.0020 (7) |
C27 | 0.0604 (10) | 0.0468 (9) | 0.0477 (9) | 0.0020 (7) | 0.0112 (7) | 0.0121 (7) |
C28 | 0.0660 (11) | 0.0575 (10) | 0.0648 (11) | 0.0005 (9) | 0.0172 (9) | 0.0160 (8) |
C29 | 0.0698 (12) | 0.0789 (14) | 0.0778 (13) | −0.0103 (10) | 0.0122 (10) | 0.0303 (11) |
C30 | 0.0956 (17) | 0.0639 (13) | 0.0779 (14) | −0.0256 (12) | −0.0035 (12) | 0.0208 (11) |
C31 | 0.1030 (17) | 0.0495 (11) | 0.0910 (15) | −0.0065 (11) | 0.0088 (13) | 0.0022 (10) |
C32 | 0.0745 (12) | 0.0492 (10) | 0.0798 (13) | 0.0032 (9) | 0.0150 (10) | 0.0040 (9) |
O1—C9 | 1.2149 (16) | C13—H13B | 0.9700 |
O2—C14 | 1.411 (2) | C14—C15 | 1.473 (3) |
O2—C12 | 1.424 (2) | C14—H14A | 0.9700 |
O3—C15 | 1.391 (3) | C14—H14B | 0.9700 |
O3—C12 | 1.4176 (18) | C15—H15A | 0.9700 |
O4—C20 | 1.2174 (19) | C15—H15B | 0.9700 |
N1—C18 | 1.462 (2) | C16—C27 | 1.512 (2) |
N1—C19 | 1.468 (2) | C16—C17 | 1.537 (2) |
N1—C17 | 1.471 (2) | C16—H16 | 0.9800 |
N2—C20 | 1.348 (2) | C17—H17A | 0.9700 |
N2—C21 | 1.405 (2) | C17—H17B | 0.9700 |
N2—H34 | 0.90 (2) | C18—H18A | 0.9600 |
C1—C6 | 1.369 (2) | C18—H18B | 0.9600 |
C1—C2 | 1.377 (3) | C18—H18C | 0.9600 |
C1—H1 | 0.9300 | C19—C26 | 1.528 (2) |
C2—C3 | 1.359 (3) | C19—C20 | 1.562 (2) |
C2—H2 | 0.9300 | C21—C22 | 1.374 (2) |
C3—C4 | 1.356 (3) | C21—C26 | 1.388 (2) |
C3—H3 | 0.9300 | C22—C23 | 1.378 (2) |
C4—C5 | 1.384 (3) | C22—H22 | 0.9300 |
C4—H4 | 0.9300 | C23—C24 | 1.368 (2) |
C5—C6 | 1.386 (2) | C23—H23 | 0.9300 |
C5—H5 | 0.9300 | C24—C25 | 1.381 (2) |
C6—C7 | 1.468 (2) | C24—H24 | 0.9300 |
C7—C8 | 1.337 (2) | C25—C26 | 1.388 (2) |
C7—H7 | 0.9300 | C25—H25 | 0.9300 |
C8—C9 | 1.491 (2) | C27—C28 | 1.386 (2) |
C8—C13 | 1.501 (2) | C27—C32 | 1.390 (2) |
C9—C10 | 1.537 (2) | C28—C29 | 1.386 (3) |
C10—C11 | 1.550 (2) | C28—H28 | 0.9300 |
C10—C16 | 1.567 (2) | C29—C30 | 1.367 (3) |
C10—C19 | 1.587 (2) | C29—H29 | 0.9300 |
C11—C12 | 1.514 (2) | C30—C31 | 1.365 (3) |
C11—H11A | 0.9700 | C30—H30 | 0.9300 |
C11—H11B | 0.9700 | C31—C32 | 1.379 (3) |
C12—C13 | 1.502 (2) | C31—H31 | 0.9300 |
C13—H13A | 0.9700 | C32—H32 | 0.9300 |
C14—O2—C12 | 107.23 (13) | C14—C15—H15A | 110.3 |
C15—O3—C12 | 108.77 (14) | O3—C15—H15B | 110.3 |
C18—N1—C19 | 114.64 (14) | C14—C15—H15B | 110.3 |
C18—N1—C17 | 113.39 (15) | H15A—C15—H15B | 108.6 |
C19—N1—C17 | 106.80 (12) | C27—C16—C17 | 117.02 (13) |
C20—N2—C21 | 112.12 (14) | C27—C16—C10 | 116.00 (13) |
C20—N2—H34 | 124.1 (12) | C17—C16—C10 | 103.83 (12) |
C21—N2—H34 | 123.3 (12) | C27—C16—H16 | 106.4 |
C6—C1—C2 | 121.37 (19) | C17—C16—H16 | 106.4 |
C6—C1—H1 | 119.3 | C10—C16—H16 | 106.4 |
C2—C1—H1 | 119.3 | N1—C17—C16 | 106.39 (13) |
C3—C2—C1 | 120.8 (2) | N1—C17—H17A | 110.5 |
C3—C2—H2 | 119.6 | C16—C17—H17A | 110.5 |
C1—C2—H2 | 119.6 | N1—C17—H17B | 110.5 |
C4—C3—C2 | 119.13 (19) | C16—C17—H17B | 110.5 |
C4—C3—H3 | 120.4 | H17A—C17—H17B | 108.6 |
C2—C3—H3 | 120.4 | N1—C18—H18A | 109.5 |
C3—C4—C5 | 120.44 (18) | N1—C18—H18B | 109.5 |
C3—C4—H4 | 119.8 | H18A—C18—H18B | 109.5 |
C5—C4—H4 | 119.8 | N1—C18—H18C | 109.5 |
C4—C5—C6 | 121.04 (18) | H18A—C18—H18C | 109.5 |
C4—C5—H5 | 119.5 | H18B—C18—H18C | 109.5 |
C6—C5—H5 | 119.5 | N1—C19—C26 | 117.99 (13) |
C1—C6—C5 | 117.13 (16) | N1—C19—C20 | 109.83 (12) |
C1—C6—C7 | 123.03 (15) | C26—C19—C20 | 100.67 (12) |
C5—C6—C7 | 119.82 (16) | N1—C19—C10 | 99.85 (11) |
C8—C7—C6 | 128.21 (16) | C26—C19—C10 | 113.46 (12) |
C8—C7—H7 | 115.9 | C20—C19—C10 | 115.80 (13) |
C6—C7—H7 | 115.9 | O4—C20—N2 | 125.11 (15) |
C7—C8—C9 | 117.92 (14) | O4—C20—C19 | 126.60 (15) |
C7—C8—C13 | 125.54 (14) | N2—C20—C19 | 108.28 (13) |
C9—C8—C13 | 116.48 (13) | C22—C21—C26 | 123.09 (15) |
O1—C9—C8 | 121.57 (13) | C22—C21—N2 | 127.33 (15) |
O1—C9—C10 | 121.59 (13) | C26—C21—N2 | 109.57 (13) |
C8—C9—C10 | 116.73 (12) | C21—C22—C23 | 117.67 (16) |
C9—C10—C11 | 111.79 (12) | C21—C22—H22 | 121.2 |
C9—C10—C16 | 112.48 (12) | C23—C22—H22 | 121.2 |
C11—C10—C16 | 112.37 (12) | C24—C23—C22 | 120.86 (16) |
C9—C10—C19 | 108.36 (11) | C24—C23—H23 | 119.6 |
C11—C10—C19 | 111.94 (12) | C22—C23—H23 | 119.6 |
C16—C10—C19 | 99.22 (12) | C23—C24—C25 | 120.88 (16) |
C12—C11—C10 | 113.41 (12) | C23—C24—H24 | 119.6 |
C12—C11—H11A | 108.9 | C25—C24—H24 | 119.6 |
C10—C11—H11A | 108.9 | C24—C25—C26 | 119.76 (16) |
C12—C11—H11B | 108.9 | C24—C25—H25 | 120.1 |
C10—C11—H11B | 108.9 | C26—C25—H25 | 120.1 |
H11A—C11—H11B | 107.7 | C21—C26—C25 | 117.68 (14) |
O3—C12—O2 | 106.42 (13) | C21—C26—C19 | 109.09 (13) |
O3—C12—C13 | 110.57 (13) | C25—C26—C19 | 133.19 (14) |
O2—C12—C13 | 108.10 (14) | C28—C27—C32 | 117.30 (16) |
O3—C12—C11 | 109.55 (13) | C28—C27—C16 | 118.51 (15) |
O2—C12—C11 | 111.54 (13) | C32—C27—C16 | 124.17 (15) |
C13—C12—C11 | 110.58 (14) | C27—C28—C29 | 121.18 (18) |
C8—C13—C12 | 109.82 (13) | C27—C28—H28 | 119.4 |
C8—C13—H13A | 109.7 | C29—C28—H28 | 119.4 |
C12—C13—H13A | 109.7 | C30—C29—C28 | 120.28 (19) |
C8—C13—H13B | 109.7 | C30—C29—H29 | 119.9 |
C12—C13—H13B | 109.7 | C28—C29—H29 | 119.9 |
H13A—C13—H13B | 108.2 | C31—C30—C29 | 119.42 (19) |
O2—C14—C15 | 104.66 (17) | C31—C30—H30 | 120.3 |
O2—C14—H14A | 110.8 | C29—C30—H30 | 120.3 |
C15—C14—H14A | 110.8 | C30—C31—C32 | 120.8 (2) |
O2—C14—H14B | 110.8 | C30—C31—H31 | 119.6 |
C15—C14—H14B | 110.8 | C32—C31—H31 | 119.6 |
H14A—C14—H14B | 108.9 | C31—C32—C27 | 120.97 (19) |
O3—C15—C14 | 107.05 (17) | C31—C32—H32 | 119.5 |
O3—C15—H15A | 110.3 | C27—C32—H32 | 119.5 |
C6—C1—C2—C3 | 0.7 (4) | C17—N1—C19—C26 | −78.91 (16) |
C1—C2—C3—C4 | −2.8 (4) | C18—N1—C19—C20 | −66.90 (19) |
C2—C3—C4—C5 | 2.0 (4) | C17—N1—C19—C20 | 166.60 (13) |
C3—C4—C5—C6 | 0.8 (3) | C18—N1—C19—C10 | 170.95 (15) |
C2—C1—C6—C5 | 2.1 (3) | C17—N1—C19—C10 | 44.45 (15) |
C2—C1—C6—C7 | −179.7 (2) | C9—C10—C19—N1 | −164.64 (11) |
C4—C5—C6—C1 | −2.8 (3) | C11—C10—C19—N1 | 71.64 (14) |
C4—C5—C6—C7 | 178.88 (16) | C16—C10—C19—N1 | −47.12 (13) |
C1—C6—C7—C8 | 30.7 (3) | C9—C10—C19—C26 | −38.16 (16) |
C5—C6—C7—C8 | −151.10 (17) | C11—C10—C19—C26 | −161.88 (12) |
C6—C7—C8—C9 | −177.82 (15) | C16—C10—C19—C26 | 79.36 (14) |
C6—C7—C8—C13 | 4.9 (3) | C9—C10—C19—C20 | 77.57 (15) |
C7—C8—C9—O1 | −25.1 (2) | C11—C10—C19—C20 | −46.16 (17) |
C13—C8—C9—O1 | 152.40 (15) | C16—C10—C19—C20 | −164.92 (12) |
C7—C8—C9—C10 | 151.08 (14) | C21—N2—C20—O4 | 174.93 (16) |
C13—C8—C9—C10 | −31.41 (19) | C21—N2—C20—C19 | −3.78 (18) |
O1—C9—C10—C11 | −142.89 (14) | N1—C19—C20—O4 | −48.5 (2) |
C8—C9—C10—C11 | 40.92 (17) | C26—C19—C20—O4 | −173.63 (17) |
O1—C9—C10—C16 | −15.4 (2) | C10—C19—C20—O4 | 63.6 (2) |
C8—C9—C10—C16 | 168.44 (12) | N1—C19—C20—N2 | 130.20 (14) |
O1—C9—C10—C19 | 93.29 (16) | C26—C19—C20—N2 | 5.05 (16) |
C8—C9—C10—C19 | −82.90 (15) | C10—C19—C20—N2 | −117.70 (15) |
C9—C10—C11—C12 | 1.45 (17) | C20—N2—C21—C22 | 179.89 (16) |
C16—C10—C11—C12 | −126.14 (14) | C20—N2—C21—C26 | 0.63 (19) |
C19—C10—C11—C12 | 123.22 (14) | C26—C21—C22—C23 | 0.6 (3) |
C15—O3—C12—O2 | 11.2 (2) | N2—C21—C22—C23 | −178.53 (16) |
C15—O3—C12—C13 | 128.3 (2) | C21—C22—C23—C24 | −2.0 (3) |
C15—O3—C12—C11 | −109.5 (2) | C22—C23—C24—C25 | 1.1 (3) |
C14—O2—C12—O3 | −22.49 (19) | C23—C24—C25—C26 | 1.2 (3) |
C14—O2—C12—C13 | −141.28 (16) | C22—C21—C26—C25 | 1.6 (2) |
C14—O2—C12—C11 | 96.94 (16) | N2—C21—C26—C25 | −179.14 (14) |
C10—C11—C12—O3 | −175.50 (12) | C22—C21—C26—C19 | −176.40 (15) |
C10—C11—C12—O2 | 66.95 (17) | N2—C21—C26—C19 | 2.89 (17) |
C10—C11—C12—C13 | −53.39 (17) | C24—C25—C26—C21 | −2.5 (2) |
C7—C8—C13—C12 | 156.55 (16) | C24—C25—C26—C19 | 174.90 (16) |
C9—C8—C13—C12 | −20.8 (2) | N1—C19—C26—C21 | −124.11 (14) |
O3—C12—C13—C8 | −174.84 (13) | C20—C19—C26—C21 | −4.70 (16) |
O2—C12—C13—C8 | −58.72 (17) | C10—C19—C26—C21 | 119.67 (14) |
C11—C12—C13—C8 | 63.64 (17) | N1—C19—C26—C25 | 58.4 (2) |
C12—O2—C14—C15 | 24.4 (2) | C20—C19—C26—C25 | 177.77 (17) |
C12—O3—C15—C14 | 3.9 (3) | C10—C19—C26—C25 | −57.9 (2) |
O2—C14—C15—O3 | −17.5 (3) | C17—C16—C27—C28 | −150.01 (15) |
C9—C10—C16—C27 | −82.41 (16) | C10—C16—C27—C28 | 86.82 (18) |
C11—C10—C16—C27 | 44.81 (17) | C17—C16—C27—C32 | 31.5 (2) |
C19—C10—C16—C27 | 163.24 (12) | C10—C16—C27—C32 | −91.68 (19) |
C9—C10—C16—C17 | 147.76 (13) | C32—C27—C28—C29 | 2.0 (3) |
C11—C10—C16—C17 | −85.03 (15) | C16—C27—C28—C29 | −176.65 (16) |
C19—C10—C16—C17 | 33.40 (14) | C27—C28—C29—C30 | −1.0 (3) |
C18—N1—C17—C16 | −150.61 (15) | C28—C29—C30—C31 | −0.4 (3) |
C19—N1—C17—C16 | −23.37 (17) | C29—C30—C31—C32 | 0.7 (3) |
C27—C16—C17—N1 | −137.40 (14) | C30—C31—C32—C27 | 0.4 (3) |
C10—C16—C17—N1 | −8.18 (17) | C28—C27—C32—C31 | −1.7 (3) |
C18—N1—C19—C26 | 47.6 (2) | C16—C27—C32—C31 | 176.86 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H34···N1i | 0.90 (2) | 2.36 (2) | 3.251 (2) | 174.3 (18) |
C4—H4···O1ii | 0.93 | 2.49 | 3.340 (2) | 152 |
C11—H11B···O4 | 0.97 | 2.27 | 3.045 (2) | 137 |
C22—H22···O4i | 0.93 | 2.43 | 3.302 (2) | 157 |
C32—H32···O4iii | 0.93 | 2.59 | 3.504 (3) | 167 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+3/2, y−1/2, −z+1/2; (iii) −x+1/2, y+1/2, −z+1/2. |
Acknowledgements
The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection.
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