research communications
Crystal structures of two substituted thiazolidine derivatives
aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
*Correspondence e-mail: shirai2011@gmail.com
In the first of the compounds reported herein, namely 6′-ferrocenyl-6a′-nitro-6′,6a′,6b′,7′,9′,11a′-hexahydro-2H-spiro[acenaphthylene-1,11′-chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazol]-2-one, [Fe(C5H5)(C29H21N2O4S)], (I), the thiazolidine ring adopts a twist conformation on the methine N—C atoms. In the second compound, viz. 6′-(4-methoxyphenyl)-6a′-nitro-6′,6a′,6b′,7′,9′,11a′-hexahydro-2H-spiro[acenaphthylene-1,11′-chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazol]-2-one, [Fe(C5H5)(C26H19N2O5S)], (II), the thiazolidine ring adopts an with a methine C atom as the flap. In both compounds, the pyrrolidine ring adopts a twist conformation on the thiazolidine and tetrahydropyran C atoms. The mean planes of the thiazolidine and pyrrolidine rings subtend angles of 67.30 (1) and 62.95 (7)° in (I) and (II), respectively, while the mean plane of the pyrrolidine ring makes dihedral angles of 76.53 (1) and 87.74 (7)° with the acenaphthylene ring system in (I) and (II), respectively. In both compounds, an intramolecular C—H⋯O hydrogen bond forms an S(7) ring motif. In the crystal of (I), molecules are linked via two different C—H⋯O hydrogen bonds, forming chains along [001] and [100]. In (II), they are linked through C—H⋯O hydrogen bonds, forming dimers with an R22(10) ring motif while C—H⋯π interactions link the molecules in a head-to-tail fashion, forming chains along the a-axis direction.
1. Chemical context
There are numerous biologically active molecules with five-membered rings containing two hetero atoms. Among them, thiazolidines are the most extensively investigated class of compounds (Fun et al., 2011). Thiazolidine derivatives have attracted continuous interest over the years because of their varied biological activities (Shih et al., 2015). The special importance of the thiazolidine ring system derives from the fact that it plays an important role in medicinal chemistry. The presence of a thiazolidine ring in penicillin and related derivatives was the first recognition of its occurrence in nature (Čačić et al., 2010). Substituted thiazolidine derivatives represent important key intermediates for the synthesis of pharmacologically active drugs. The group has wide range of biological activities such as antifungal, antiproliferative, anti-inflammatory, antimalarial, herbicidal, antiviral (Samadhiya et al., 2012), anticonvulsant (Pandey et al., 2011), anticancer and anti-oxidant, and also has interesting antimicrobial activity (influenza). In addition, antidiabetic properties (Majed & Abid, 2015) have been reported. Thiazolidine derivatives exhibit anti-HIV, antituberculotic (Fun et al., 2011), herbicidal, antineoplastic, hypolipidemic and anti-inflammatory activities (Vennila et al., 2011). Thiazolidines have many interesting activity profiles, namely as COX-1 inhibitors, inhibitors of the bacterial enzyme MurB, which is a precursor, acting during the biosynthesis of non-nucleoside inhibitors of HIV–RT and anti-histaminic agents (Čačić et al., 2010).
2. Structural commentary
In the molecular structures of the compounds reported herein, namely 2′-ferrocenyl-6′-methyl-6a′-nitro-6′,6a′,6b′,7′,9′,11a′-hexahydro-2H-spiro[acenaphthylene-1,11′-chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazol]-2-one, (I) (Fig. 1), and 6′-(4-methoxyphenyl)-6a′-nitro-6′,6a′,6b′,7′,9′,11a′-hexahydro-2H-spiro[acenaphthylene-1,11′-chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazol]-2-one, (II) (Fig. 2), the pyrrolidine ring (C12/N1/C15–C17) is fused with the thiazolidine ring (N1/C13/S1/C14/C15), the chromane ring system (C16–C23/O2/C24) and the acenaphthylene ring system (C1–C12). The thiazolidine ring adopts a twist conformation on the N1—C15 bond with puckering parameters q2 = 0.3710 (8) Å, Φ2 = 96.7 (3)° in (I) and an with atom C15 as the flap in (II). The pyrrolidine ring adopts a twist conformation on the C15—C16 bond with puckering parameters q2 = 0.3616 (7) Å and Φ2 = 131.3 (3)°, and q2 = 0.3829 (8) Å and Φ2 = 123.4 (3)° in the structures of (I) and (II), respectively. The mean planes of the thiazolidine and pyrrolidine rings are inclined to one another by 67.30 (1) and 62.95 (7)°, while the pyrrolidine and acenaphthylene ring systems are almost orthogonal to each other [dihedral angles = 76.53 (1) and 87.74 (7)°, respectively]. The chromane ring system adopts a distorted the flaps being atom C24 in (I), displaced by −0.5585 (1) Å, and atom C16 in (II), displaced by 0.4076 (3) Å.
The pyrrolidine and the chromane ring systems subtend dihedral angles of 74.94 (8) and 67.68 (7)° in (I) and (II), respectively. In (I), the chromane and ferrocene ring systems lie in a plane [C17—C16—C24—C25 = 176.16 (13)° and C23—O2—C24—C25 = −177.50 (13)°]. In (II), the chromane ring system makes a dihedral angle of 62.58 (4)° with the phenyl ring. Atom O1 deviates from the acenaphthylene ring system by −0.0718 (4) and −0.2218 (3) Å in (I) and (II), respectively.
In both compounds, an intramolecular C—H⋯O hydrogen bond forms an S(7) ring motif (Figs. 1 and 2; Tables 1 and 2).
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3. Supramolecular features
In the crystal of (I), molecules are linked via C—H⋯O hydrogen bonds along [001] and [100] (Fig. 3 and Table 1), generating planes parallel to (010) with embedded R44(29) ring motifs. In the crystal of (II), molecules are linked via C—H⋯O hydrogen bonds, forming dimers with an (10) ring motif, as shown in Fig. 4 and Table 2. C—H⋯π interactions link the molecules in a head-to-tail fashion, forming chains extending along [100] (Fig. 5).
4. Synthesis and crystallization
Both compounds were obtained through a similar procedure. To a solution of acenaphthoquinone (1.0 mmol) and thiazolidine-4-carboxylic acid (1.5 mmol) in dry toluene, were added under nitrogen atmosphere 3-nitro-2-ferrocenyl-2H-chromene (1 mmol), for compound (I), or 2-(4-methoxyphenyl)-3-nitro-2H-chromene (1 mmol) for compound (II). The solutions were refluxed for 18 h in a Dean–Stark apparatus to give the corresponding cycloadduct. After completion of the reaction as indicated by TLC, the solvent was evaporated under reduced pressure. The crude product obtained was purified by using hexane/EtOAc (8:2) as [Yields: 91% for (I), 88% for (II)].
5. Refinement
Crystal data, data collection and structure . The hydrogen atoms were placed in calculated positions with C—H = 0.93–0.98 Å and refined using a riding model with fixed isotropic displacement parameters: Uiso(H) = 1.5Ueq(C) for the methyl group and Uiso(H) = 1.2Ueq(C) for the remaining H atoms.
details are summarized in Table 3
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Supporting information
https://doi.org/10.1107/S2056989016011336/bg2588sup1.cif
contains datablocks global, I, II. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989016011336/bg2588Isup2.hkl
Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989016011336/bg2588IIsup3.hkl
For both compounds, data collection: APEX2 (Bruker, 2008); cell
APEX2 (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).[Fe(C5H5)(C29H21N2O4S)] | F(000) = 1272 |
Mr = 614.48 | Dx = 1.477 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 11.782 (5) Å | Cell parameters from 6900 reflections |
b = 16.741 (5) Å | θ = 1.9–28.3° |
c = 14.147 (5) Å | µ = 0.67 mm−1 |
β = 98.013 (5)° | T = 293 K |
V = 2763.1 (17) Å3 | Block, colourless |
Z = 4 | 0.19 × 0.16 × 0.11 mm |
Bruker SMART APEXII area-detector diffractometer | 5281 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.028 |
ω and φ scans | θmax = 28.3°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −15→12 |
Tmin = 0.746, Tmax = 0.845 | k = −22→20 |
25994 measured reflections | l = −16→18 |
6900 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.035 | H-atom parameters constrained |
wR(F2) = 0.097 | w = 1/[σ2(Fo2) + (0.0472P)2 + 0.6353P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
6900 reflections | Δρmax = 0.29 e Å−3 |
379 parameters | Δρmin = −0.33 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 | ||
C1 | 0.17168 (14) | 0.29715 (10) | 0.34129 (12) | 0.0382 (4) | |
C2 | 0.27528 (15) | 0.26349 (12) | 0.30982 (13) | 0.0437 (4) | |
C3 | 0.36894 (17) | 0.29875 (15) | 0.27815 (15) | 0.0580 (5) | |
H3 | 0.3751 | 0.3540 | 0.2741 | 0.070* | |
C4 | 0.45406 (18) | 0.24843 (19) | 0.25235 (17) | 0.0714 (7) | |
H4 | 0.5173 | 0.2713 | 0.2301 | 0.086* | |
C5 | 0.44852 (18) | 0.16710 (18) | 0.25835 (16) | 0.0683 (7) | |
H5 | 0.5081 | 0.1363 | 0.2412 | 0.082* | |
C6 | 0.35397 (17) | 0.12899 (14) | 0.29018 (14) | 0.0536 (5) | |
C7 | 0.3351 (2) | 0.04678 (15) | 0.30007 (16) | 0.0660 (6) | |
H7 | 0.3897 | 0.0103 | 0.2855 | 0.079* | |
C8 | 0.2377 (2) | 0.02016 (13) | 0.33066 (17) | 0.0649 (6) | |
H8 | 0.2277 | −0.0346 | 0.3372 | 0.078* | |
C9 | 0.15032 (19) | 0.07272 (11) | 0.35320 (15) | 0.0528 (5) | |
H9 | 0.0834 | 0.0526 | 0.3720 | 0.063* | |
C10 | 0.16661 (15) | 0.15301 (10) | 0.34672 (12) | 0.0397 (4) | |
C11 | 0.26808 (15) | 0.18037 (11) | 0.31521 (12) | 0.0409 (4) | |
C12 | 0.09371 (13) | 0.22504 (9) | 0.36526 (11) | 0.0327 (3) | |
C13 | 0.13859 (17) | 0.19957 (12) | 0.54151 (13) | 0.0478 (4) | |
H13A | 0.1502 | 0.2351 | 0.5961 | 0.057* | |
H13B | 0.2128 | 0.1863 | 0.5235 | 0.057* | |
C14 | −0.06611 (17) | 0.13300 (11) | 0.49327 (14) | 0.0489 (5) | |
H14A | −0.0738 | 0.1007 | 0.4358 | 0.059* | |
H14B | −0.1330 | 0.1248 | 0.5250 | 0.059* | |
C15 | −0.05289 (14) | 0.22215 (9) | 0.46914 (11) | 0.0344 (3) | |
H15 | −0.0782 | 0.2554 | 0.5193 | 0.041* | |
C16 | −0.10955 (13) | 0.25086 (9) | 0.37114 (11) | 0.0302 (3) | |
C17 | −0.02634 (13) | 0.22598 (9) | 0.30174 (11) | 0.0305 (3) | |
H17 | −0.0450 | 0.1711 | 0.2810 | 0.037* | |
C18 | −0.03280 (14) | 0.27774 (10) | 0.21409 (11) | 0.0335 (3) | |
C19 | 0.02668 (16) | 0.25728 (12) | 0.13894 (13) | 0.0445 (4) | |
H19 | 0.0699 | 0.2106 | 0.1426 | 0.053* | |
C20 | 0.02230 (19) | 0.30546 (14) | 0.05904 (14) | 0.0562 (5) | |
H20 | 0.0621 | 0.2911 | 0.0093 | 0.067* | |
C21 | −0.04142 (19) | 0.37487 (13) | 0.05351 (13) | 0.0556 (5) | |
H21 | −0.0439 | 0.4075 | 0.0000 | 0.067* | |
C22 | −0.10152 (17) | 0.39641 (11) | 0.12664 (12) | 0.0462 (4) | |
H22 | −0.1445 | 0.4432 | 0.1228 | 0.055* | |
C23 | −0.09665 (14) | 0.34702 (10) | 0.20609 (11) | 0.0351 (3) | |
C24 | −0.12592 (14) | 0.34274 (9) | 0.36993 (10) | 0.0310 (3) | |
H24 | −0.0518 | 0.3674 | 0.3930 | 0.037* | |
C25 | −0.21170 (15) | 0.37219 (9) | 0.43064 (11) | 0.0360 (4) | |
C26 | −0.1857 (2) | 0.41094 (13) | 0.52068 (13) | 0.0546 (5) | |
H26 | −0.1090 | 0.4222 | 0.5545 | 0.065* | |
C27 | −0.2915 (2) | 0.43003 (14) | 0.55249 (15) | 0.0691 (7) | |
H27 | −0.3003 | 0.4579 | 0.6119 | 0.083* | |
C28 | −0.3806 (2) | 0.40483 (13) | 0.48430 (18) | 0.0621 (6) | |
H28 | −0.4625 | 0.4114 | 0.4878 | 0.074* | |
C29 | −0.33282 (16) | 0.36859 (11) | 0.40861 (16) | 0.0476 (4) | |
H29 | −0.3759 | 0.3454 | 0.3508 | 0.057* | |
C30 | −0.1999 (2) | 0.54692 (11) | 0.33192 (16) | 0.0600 (6) | |
H30 | −0.1325 | 0.5299 | 0.3037 | 0.072* | |
C31 | −0.1986 (2) | 0.59003 (12) | 0.41768 (18) | 0.0629 (6) | |
H31 | −0.1301 | 0.6078 | 0.4598 | 0.075* | |
C32 | −0.3126 (2) | 0.60257 (11) | 0.43236 (16) | 0.0586 (6) | |
H32 | −0.3377 | 0.6305 | 0.4867 | 0.070* | |
C33 | −0.3842 (2) | 0.56757 (12) | 0.35621 (16) | 0.0595 (5) | |
H33 | −0.4682 | 0.5671 | 0.3477 | 0.071* | |
C34 | −0.3144 (2) | 0.53302 (12) | 0.29394 (14) | 0.0591 (6) | |
H34 | −0.3413 | 0.5048 | 0.2343 | 0.071* | |
N1 | 0.06793 (12) | 0.23745 (8) | 0.46323 (9) | 0.0346 (3) | |
N2 | −0.22575 (12) | 0.21372 (8) | 0.34208 (11) | 0.0363 (3) | |
O1 | 0.14788 (12) | 0.36653 (7) | 0.35017 (10) | 0.0508 (3) | |
O2 | −0.16222 (11) | 0.37057 (7) | 0.27473 (8) | 0.0390 (3) | |
O3 | −0.26393 (11) | 0.21596 (8) | 0.25751 (9) | 0.0492 (3) | |
O4 | −0.27784 (11) | 0.18748 (9) | 0.40367 (11) | 0.0580 (4) | |
S1 | 0.06376 (5) | 0.10735 (3) | 0.57181 (4) | 0.06071 (16) | |
Fe1 | −0.27986 (2) | 0.48313 (2) | 0.42494 (2) | 0.03501 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0313 (9) | 0.0423 (9) | 0.0401 (9) | −0.0019 (7) | 0.0014 (7) | −0.0009 (7) |
C2 | 0.0288 (9) | 0.0600 (11) | 0.0413 (9) | −0.0012 (8) | 0.0016 (7) | −0.0017 (8) |
C3 | 0.0392 (11) | 0.0821 (15) | 0.0526 (12) | −0.0127 (10) | 0.0066 (9) | −0.0002 (10) |
C4 | 0.0352 (11) | 0.125 (2) | 0.0563 (13) | −0.0084 (13) | 0.0130 (10) | −0.0133 (14) |
C5 | 0.0345 (11) | 0.117 (2) | 0.0537 (13) | 0.0167 (12) | 0.0063 (9) | −0.0229 (13) |
C6 | 0.0384 (10) | 0.0803 (15) | 0.0400 (10) | 0.0192 (10) | −0.0023 (8) | −0.0148 (9) |
C7 | 0.0633 (15) | 0.0755 (15) | 0.0566 (13) | 0.0355 (12) | −0.0007 (11) | −0.0184 (11) |
C8 | 0.0830 (17) | 0.0436 (11) | 0.0657 (14) | 0.0229 (11) | 0.0015 (13) | −0.0096 (9) |
C9 | 0.0585 (13) | 0.0423 (10) | 0.0584 (12) | 0.0086 (9) | 0.0105 (10) | −0.0052 (9) |
C10 | 0.0375 (9) | 0.0413 (9) | 0.0400 (9) | 0.0090 (7) | 0.0044 (7) | −0.0042 (7) |
C11 | 0.0312 (9) | 0.0562 (11) | 0.0340 (9) | 0.0100 (8) | −0.0003 (7) | −0.0066 (7) |
C12 | 0.0286 (8) | 0.0324 (8) | 0.0369 (8) | 0.0029 (6) | 0.0038 (6) | −0.0023 (6) |
C13 | 0.0474 (11) | 0.0517 (11) | 0.0411 (10) | 0.0094 (8) | −0.0045 (8) | 0.0007 (8) |
C14 | 0.0484 (11) | 0.0448 (10) | 0.0539 (11) | 0.0039 (8) | 0.0082 (9) | 0.0155 (8) |
C15 | 0.0358 (9) | 0.0373 (8) | 0.0307 (8) | 0.0051 (7) | 0.0072 (7) | 0.0016 (6) |
C16 | 0.0268 (8) | 0.0320 (8) | 0.0318 (8) | 0.0013 (6) | 0.0039 (6) | −0.0004 (6) |
C17 | 0.0284 (8) | 0.0312 (7) | 0.0323 (8) | 0.0007 (6) | 0.0060 (6) | −0.0034 (6) |
C18 | 0.0308 (8) | 0.0406 (8) | 0.0290 (8) | −0.0047 (7) | 0.0039 (6) | −0.0044 (6) |
C19 | 0.0424 (10) | 0.0546 (11) | 0.0384 (9) | −0.0024 (8) | 0.0120 (8) | −0.0084 (8) |
C20 | 0.0576 (13) | 0.0762 (14) | 0.0389 (10) | −0.0099 (11) | 0.0215 (9) | −0.0057 (9) |
C21 | 0.0658 (14) | 0.0681 (13) | 0.0338 (9) | −0.0130 (11) | 0.0101 (9) | 0.0091 (9) |
C22 | 0.0532 (12) | 0.0482 (10) | 0.0364 (9) | −0.0053 (8) | 0.0029 (8) | 0.0054 (7) |
C23 | 0.0352 (9) | 0.0418 (9) | 0.0284 (8) | −0.0051 (7) | 0.0045 (6) | −0.0022 (6) |
C24 | 0.0328 (8) | 0.0317 (8) | 0.0285 (7) | 0.0022 (6) | 0.0045 (6) | 0.0005 (6) |
C25 | 0.0406 (9) | 0.0341 (8) | 0.0341 (8) | 0.0090 (7) | 0.0083 (7) | 0.0049 (6) |
C26 | 0.0668 (13) | 0.0656 (12) | 0.0300 (9) | 0.0278 (10) | 0.0021 (9) | 0.0005 (8) |
C27 | 0.100 (2) | 0.0739 (15) | 0.0400 (11) | 0.0418 (14) | 0.0312 (13) | 0.0130 (10) |
C28 | 0.0616 (14) | 0.0558 (12) | 0.0778 (16) | 0.0136 (10) | 0.0413 (13) | 0.0157 (11) |
C29 | 0.0403 (10) | 0.0371 (9) | 0.0687 (12) | −0.0014 (8) | 0.0191 (9) | −0.0013 (8) |
C30 | 0.0800 (16) | 0.0359 (10) | 0.0717 (14) | −0.0013 (10) | 0.0380 (13) | 0.0044 (9) |
C31 | 0.0682 (15) | 0.0406 (10) | 0.0811 (16) | −0.0106 (10) | 0.0151 (12) | −0.0122 (10) |
C32 | 0.0757 (15) | 0.0358 (10) | 0.0663 (14) | 0.0118 (9) | 0.0172 (12) | −0.0083 (9) |
C33 | 0.0657 (14) | 0.0489 (11) | 0.0620 (13) | 0.0194 (10) | 0.0019 (11) | 0.0094 (10) |
C34 | 0.0931 (18) | 0.0450 (11) | 0.0387 (10) | 0.0105 (11) | 0.0074 (11) | 0.0085 (8) |
N1 | 0.0331 (7) | 0.0372 (7) | 0.0323 (7) | 0.0056 (6) | 0.0005 (6) | −0.0015 (5) |
N2 | 0.0288 (7) | 0.0346 (7) | 0.0460 (8) | 0.0028 (6) | 0.0071 (6) | −0.0001 (6) |
O1 | 0.0481 (8) | 0.0373 (7) | 0.0668 (9) | −0.0048 (6) | 0.0071 (7) | −0.0017 (6) |
O2 | 0.0476 (7) | 0.0409 (6) | 0.0292 (6) | 0.0123 (5) | 0.0078 (5) | 0.0049 (5) |
O3 | 0.0339 (7) | 0.0675 (9) | 0.0444 (7) | −0.0035 (6) | −0.0003 (6) | −0.0090 (6) |
O4 | 0.0411 (8) | 0.0710 (9) | 0.0645 (9) | −0.0105 (7) | 0.0165 (7) | 0.0170 (7) |
S1 | 0.0694 (4) | 0.0521 (3) | 0.0579 (3) | 0.0147 (3) | −0.0006 (3) | 0.0201 (2) |
Fe1 | 0.03822 (15) | 0.03383 (13) | 0.03325 (13) | 0.00572 (10) | 0.00597 (10) | −0.00222 (9) |
C1—O1 | 1.205 (2) | C19—H19 | 0.9300 |
C1—C2 | 1.469 (2) | C20—C21 | 1.380 (3) |
C1—C12 | 1.582 (2) | C20—H20 | 0.9300 |
C2—C3 | 1.380 (3) | C21—C22 | 1.380 (3) |
C2—C11 | 1.397 (3) | C21—H21 | 0.9300 |
C3—C4 | 1.397 (3) | C22—C23 | 1.390 (2) |
C3—H3 | 0.9300 | C22—H22 | 0.9300 |
C4—C5 | 1.366 (4) | C23—O2 | 1.3799 (19) |
C4—H4 | 0.9300 | C24—O2 | 1.4330 (19) |
C5—C6 | 1.411 (3) | C24—C25 | 1.498 (2) |
C5—H5 | 0.9300 | C24—H24 | 0.9800 |
C6—C7 | 1.404 (3) | C25—C29 | 1.419 (3) |
C6—C11 | 1.410 (2) | C25—C26 | 1.424 (3) |
C7—C8 | 1.357 (4) | C25—Fe1 | 2.0206 (16) |
C7—H7 | 0.9300 | C26—C27 | 1.419 (3) |
C8—C9 | 1.424 (3) | C26—Fe1 | 2.0263 (19) |
C8—H8 | 0.9300 | C26—H26 | 0.9800 |
C9—C10 | 1.363 (3) | C27—C28 | 1.388 (4) |
C9—H9 | 0.9300 | C27—Fe1 | 2.033 (2) |
C10—C11 | 1.409 (3) | C27—H27 | 0.9800 |
C10—C12 | 1.524 (2) | C28—C29 | 1.414 (3) |
C12—N1 | 1.474 (2) | C28—Fe1 | 2.027 (2) |
C12—C17 | 1.566 (2) | C28—H28 | 0.9800 |
C13—N1 | 1.437 (2) | C29—Fe1 | 2.0197 (19) |
C13—S1 | 1.857 (2) | C29—H29 | 0.9800 |
C13—H13A | 0.9700 | C30—C34 | 1.401 (3) |
C13—H13B | 0.9700 | C30—C31 | 1.410 (3) |
C14—C15 | 1.544 (2) | C30—Fe1 | 2.026 (2) |
C14—S1 | 1.813 (2) | C30—H30 | 0.9800 |
C14—H14A | 0.9700 | C31—C32 | 1.403 (3) |
C14—H14B | 0.9700 | C31—Fe1 | 2.039 (2) |
C15—N1 | 1.460 (2) | C31—H31 | 0.9800 |
C15—C16 | 1.530 (2) | C32—C33 | 1.401 (3) |
C15—H15 | 0.9800 | C32—Fe1 | 2.042 (2) |
C16—N2 | 1.508 (2) | C32—H32 | 0.9800 |
C16—C17 | 1.538 (2) | C33—C34 | 1.410 (3) |
C16—C24 | 1.550 (2) | C33—Fe1 | 2.030 (2) |
C17—C18 | 1.506 (2) | C33—H33 | 0.9800 |
C17—H17 | 0.9800 | C34—Fe1 | 2.022 (2) |
C18—C23 | 1.378 (2) | C34—H34 | 0.9800 |
C18—C19 | 1.395 (2) | N2—O4 | 1.2158 (19) |
C19—C20 | 1.384 (3) | N2—O3 | 1.2186 (19) |
O1—C1—C2 | 128.05 (16) | C25—C26—H26 | 126.3 |
O1—C1—C12 | 124.22 (15) | Fe1—C26—H26 | 126.3 |
C2—C1—C12 | 107.71 (14) | C28—C27—C26 | 108.86 (19) |
C3—C2—C11 | 120.08 (18) | C28—C27—Fe1 | 69.77 (12) |
C3—C2—C1 | 132.09 (19) | C26—C27—Fe1 | 69.27 (11) |
C11—C2—C1 | 107.83 (15) | C28—C27—H27 | 125.6 |
C2—C3—C4 | 117.6 (2) | C26—C27—H27 | 125.6 |
C2—C3—H3 | 121.2 | Fe1—C27—H27 | 125.6 |
C4—C3—H3 | 121.2 | C27—C28—C29 | 108.34 (19) |
C5—C4—C3 | 122.9 (2) | C27—C28—Fe1 | 70.25 (13) |
C5—C4—H4 | 118.6 | C29—C28—Fe1 | 69.27 (11) |
C3—C4—H4 | 118.6 | C27—C28—H28 | 125.8 |
C4—C5—C6 | 121.1 (2) | C29—C28—H28 | 125.8 |
C4—C5—H5 | 119.4 | Fe1—C28—H28 | 125.8 |
C6—C5—H5 | 119.4 | C28—C29—C25 | 108.0 (2) |
C7—C6—C11 | 116.3 (2) | C28—C29—Fe1 | 69.84 (12) |
C7—C6—C5 | 128.2 (2) | C25—C29—Fe1 | 69.47 (10) |
C11—C6—C5 | 115.5 (2) | C28—C29—H29 | 126.0 |
C8—C7—C6 | 120.43 (19) | C25—C29—H29 | 126.0 |
C8—C7—H7 | 119.8 | Fe1—C29—H29 | 126.0 |
C6—C7—H7 | 119.8 | C34—C30—C31 | 108.0 (2) |
C7—C8—C9 | 122.6 (2) | C34—C30—Fe1 | 69.59 (12) |
C7—C8—H8 | 118.7 | C31—C30—Fe1 | 70.19 (12) |
C9—C8—H8 | 118.7 | C34—C30—H30 | 126.0 |
C10—C9—C8 | 118.8 (2) | C31—C30—H30 | 126.0 |
C10—C9—H9 | 120.6 | Fe1—C30—H30 | 126.0 |
C8—C9—H9 | 120.6 | C32—C31—C30 | 108.0 (2) |
C9—C10—C11 | 118.39 (16) | C32—C31—Fe1 | 70.00 (12) |
C9—C10—C12 | 132.91 (17) | C30—C31—Fe1 | 69.22 (11) |
C11—C10—C12 | 108.70 (15) | C32—C31—H31 | 126.0 |
C2—C11—C10 | 113.68 (15) | C30—C31—H31 | 126.0 |
C2—C11—C6 | 122.87 (18) | Fe1—C31—H31 | 126.0 |
C10—C11—C6 | 123.45 (19) | C33—C32—C31 | 108.0 (2) |
N1—C12—C10 | 117.90 (13) | C33—C32—Fe1 | 69.43 (11) |
N1—C12—C17 | 104.47 (12) | C31—C32—Fe1 | 69.79 (11) |
C10—C12—C17 | 113.24 (13) | C33—C32—H32 | 126.0 |
N1—C12—C1 | 107.21 (13) | C31—C32—H32 | 126.0 |
C10—C12—C1 | 102.06 (13) | Fe1—C32—H32 | 126.0 |
C17—C12—C1 | 111.98 (13) | C32—C33—C34 | 108.1 (2) |
N1—C13—S1 | 107.58 (13) | C32—C33—Fe1 | 70.32 (12) |
N1—C13—H13A | 110.2 | C34—C33—Fe1 | 69.32 (12) |
S1—C13—H13A | 110.2 | C32—C33—H33 | 125.9 |
N1—C13—H13B | 110.2 | C34—C33—H33 | 125.9 |
S1—C13—H13B | 110.2 | Fe1—C33—H33 | 125.9 |
H13A—C13—H13B | 108.5 | C30—C34—C33 | 107.9 (2) |
C15—C14—S1 | 105.19 (13) | C30—C34—Fe1 | 69.93 (12) |
C15—C14—H14A | 110.7 | C33—C34—Fe1 | 69.95 (12) |
S1—C14—H14A | 110.7 | C30—C34—H34 | 126.1 |
C15—C14—H14B | 110.7 | C33—C34—H34 | 126.1 |
S1—C14—H14B | 110.7 | Fe1—C34—H34 | 126.1 |
H14A—C14—H14B | 108.8 | C13—N1—C15 | 110.07 (14) |
N1—C15—C16 | 101.46 (12) | C13—N1—C12 | 119.29 (14) |
N1—C15—C14 | 108.15 (13) | C15—N1—C12 | 111.06 (13) |
C16—C15—C14 | 117.35 (14) | O4—N2—O3 | 124.10 (15) |
N1—C15—H15 | 109.8 | O4—N2—C16 | 118.91 (14) |
C16—C15—H15 | 109.8 | O3—N2—C16 | 116.87 (13) |
C14—C15—H15 | 109.8 | C23—O2—C24 | 116.45 (12) |
N2—C16—C15 | 112.49 (13) | C14—S1—C13 | 92.80 (9) |
N2—C16—C17 | 110.46 (12) | C29—Fe1—C25 | 41.12 (8) |
C15—C16—C17 | 104.88 (12) | C29—Fe1—C34 | 105.54 (9) |
N2—C16—C24 | 107.42 (12) | C25—Fe1—C34 | 116.39 (8) |
C15—C16—C24 | 111.08 (12) | C29—Fe1—C30 | 126.18 (8) |
C17—C16—C24 | 110.55 (12) | C25—Fe1—C30 | 106.99 (8) |
C18—C17—C16 | 113.96 (13) | C34—Fe1—C30 | 40.48 (10) |
C18—C17—C12 | 114.58 (13) | C29—Fe1—C26 | 69.01 (9) |
C16—C17—C12 | 103.97 (12) | C25—Fe1—C26 | 41.21 (7) |
C18—C17—H17 | 108.0 | C34—Fe1—C26 | 151.72 (9) |
C16—C17—H17 | 108.0 | C30—Fe1—C26 | 119.19 (10) |
C12—C17—H17 | 108.0 | C29—Fe1—C28 | 40.89 (8) |
C23—C18—C19 | 118.06 (16) | C25—Fe1—C28 | 68.99 (8) |
C23—C18—C17 | 121.07 (14) | C34—Fe1—C28 | 126.31 (11) |
C19—C18—C17 | 120.87 (15) | C30—Fe1—C28 | 164.13 (11) |
C20—C19—C18 | 120.93 (19) | C26—Fe1—C28 | 68.58 (10) |
C20—C19—H19 | 119.5 | C29—Fe1—C33 | 116.71 (9) |
C18—C19—H19 | 119.5 | C25—Fe1—C33 | 150.45 (8) |
C21—C20—C19 | 119.68 (17) | C34—Fe1—C33 | 40.73 (9) |
C21—C20—H20 | 120.2 | C30—Fe1—C33 | 68.12 (10) |
C19—C20—H20 | 120.2 | C26—Fe1—C33 | 166.86 (8) |
C20—C21—C22 | 120.62 (18) | C28—Fe1—C33 | 107.36 (10) |
C20—C21—H21 | 119.7 | C29—Fe1—C27 | 68.18 (10) |
C22—C21—H21 | 119.7 | C25—Fe1—C27 | 68.80 (7) |
C21—C22—C23 | 118.88 (19) | C34—Fe1—C27 | 164.63 (11) |
C21—C22—H22 | 120.6 | C30—Fe1—C27 | 154.40 (12) |
C23—C22—H22 | 120.6 | C26—Fe1—C27 | 40.93 (9) |
C18—C23—O2 | 122.36 (14) | C28—Fe1—C27 | 39.98 (10) |
C18—C23—C22 | 121.83 (16) | C33—Fe1—C27 | 128.18 (9) |
O2—C23—C22 | 115.78 (15) | C29—Fe1—C31 | 165.30 (8) |
O2—C24—C25 | 107.16 (13) | C25—Fe1—C31 | 128.46 (9) |
O2—C24—C16 | 110.69 (12) | C34—Fe1—C31 | 68.11 (10) |
C25—C24—C16 | 114.40 (13) | C30—Fe1—C31 | 40.58 (9) |
O2—C24—H24 | 108.1 | C26—Fe1—C31 | 109.88 (10) |
C25—C24—H24 | 108.1 | C28—Fe1—C31 | 153.45 (9) |
C16—C24—H24 | 108.1 | C33—Fe1—C31 | 67.79 (10) |
C29—C25—C26 | 107.44 (16) | C27—Fe1—C31 | 121.25 (11) |
C29—C25—C24 | 126.76 (16) | C29—Fe1—C32 | 151.41 (9) |
C26—C25—C24 | 125.79 (17) | C25—Fe1—C32 | 167.14 (9) |
C29—C25—Fe1 | 69.41 (10) | C34—Fe1—C32 | 68.12 (9) |
C26—C25—Fe1 | 69.61 (10) | C30—Fe1—C32 | 68.01 (9) |
C24—C25—Fe1 | 125.15 (11) | C26—Fe1—C32 | 129.74 (9) |
C27—C26—C25 | 107.3 (2) | C28—Fe1—C32 | 119.10 (9) |
C27—C26—Fe1 | 69.80 (12) | C33—Fe1—C32 | 40.25 (9) |
C25—C26—Fe1 | 69.18 (10) | C27—Fe1—C32 | 110.24 (9) |
C27—C26—H26 | 126.3 | C31—Fe1—C32 | 40.22 (9) |
O1—C1—C2—C3 | −3.5 (3) | C21—C22—C23—C18 | 0.6 (3) |
C12—C1—C2—C3 | 177.9 (2) | C21—C22—C23—O2 | −177.60 (17) |
O1—C1—C2—C11 | 177.00 (18) | N2—C16—C24—O2 | −65.60 (15) |
C12—C1—C2—C11 | −1.61 (19) | C15—C16—C24—O2 | 171.00 (12) |
C11—C2—C3—C4 | 0.0 (3) | C17—C16—C24—O2 | 54.99 (17) |
C1—C2—C3—C4 | −179.4 (2) | N2—C16—C24—C25 | 55.58 (17) |
C2—C3—C4—C5 | −0.8 (3) | C15—C16—C24—C25 | −67.83 (18) |
C3—C4—C5—C6 | 1.0 (4) | C17—C16—C24—C25 | 176.16 (13) |
C4—C5—C6—C7 | 179.8 (2) | O2—C24—C25—C29 | 46.3 (2) |
C4—C5—C6—C11 | −0.3 (3) | C16—C24—C25—C29 | −76.8 (2) |
C11—C6—C7—C8 | 1.1 (3) | O2—C24—C25—C26 | −132.02 (17) |
C5—C6—C7—C8 | −179.0 (2) | C16—C24—C25—C26 | 104.88 (19) |
C6—C7—C8—C9 | 0.6 (4) | O2—C24—C25—Fe1 | −43.03 (18) |
C7—C8—C9—C10 | −2.1 (3) | C16—C24—C25—Fe1 | −166.13 (11) |
C8—C9—C10—C11 | 1.8 (3) | C29—C25—C26—C27 | 0.3 (2) |
C8—C9—C10—C12 | −179.70 (19) | C24—C25—C26—C27 | 178.93 (16) |
C3—C2—C11—C10 | −178.66 (17) | Fe1—C25—C26—C27 | 59.64 (14) |
C1—C2—C11—C10 | 0.9 (2) | C29—C25—C26—Fe1 | −59.33 (12) |
C3—C2—C11—C6 | 0.6 (3) | C24—C25—C26—Fe1 | 119.29 (16) |
C1—C2—C11—C6 | −179.89 (16) | C25—C26—C27—C28 | −0.6 (2) |
C9—C10—C11—C2 | 179.08 (17) | Fe1—C26—C27—C28 | 58.67 (15) |
C12—C10—C11—C2 | 0.3 (2) | C25—C26—C27—Fe1 | −59.25 (13) |
C9—C10—C11—C6 | −0.1 (3) | C26—C27—C28—C29 | 0.6 (2) |
C12—C10—C11—C6 | −178.96 (16) | Fe1—C27—C28—C29 | 58.98 (14) |
C7—C6—C11—C2 | 179.51 (18) | C26—C27—C28—Fe1 | −58.37 (15) |
C5—C6—C11—C2 | −0.4 (3) | C27—C28—C29—C25 | −0.4 (2) |
C7—C6—C11—C10 | −1.3 (3) | Fe1—C28—C29—C25 | 59.17 (12) |
C5—C6—C11—C10 | 178.75 (18) | C27—C28—C29—Fe1 | −59.59 (15) |
C9—C10—C12—N1 | 63.2 (3) | C26—C25—C29—C28 | 0.1 (2) |
C11—C10—C12—N1 | −118.28 (16) | C24—C25—C29—C28 | −178.55 (16) |
C9—C10—C12—C17 | −59.2 (3) | Fe1—C25—C29—C28 | −59.40 (13) |
C11—C10—C12—C17 | 119.36 (15) | C26—C25—C29—Fe1 | 59.46 (13) |
C9—C10—C12—C1 | −179.8 (2) | C24—C25—C29—Fe1 | −119.15 (16) |
C11—C10—C12—C1 | −1.18 (17) | C34—C30—C31—C32 | 0.0 (2) |
O1—C1—C12—N1 | −52.4 (2) | Fe1—C30—C31—C32 | −59.50 (15) |
C2—C1—C12—N1 | 126.23 (14) | C34—C30—C31—Fe1 | 59.54 (14) |
O1—C1—C12—C10 | −177.00 (17) | C30—C31—C32—C33 | −0.1 (2) |
C2—C1—C12—C10 | 1.68 (17) | Fe1—C31—C32—C33 | −59.08 (15) |
O1—C1—C12—C17 | 61.6 (2) | C30—C31—C32—Fe1 | 59.01 (15) |
C2—C1—C12—C17 | −119.74 (15) | C31—C32—C33—C34 | 0.1 (2) |
S1—C14—C15—N1 | 34.99 (16) | Fe1—C32—C33—C34 | −59.23 (14) |
S1—C14—C15—C16 | 148.88 (12) | C31—C32—C33—Fe1 | 59.30 (15) |
N1—C15—C16—N2 | 157.43 (12) | C31—C30—C34—C33 | 0.0 (2) |
C14—C15—C16—N2 | 39.87 (19) | Fe1—C30—C34—C33 | 59.93 (14) |
N1—C15—C16—C17 | 37.33 (15) | C31—C30—C34—Fe1 | −59.92 (15) |
C14—C15—C16—C17 | −80.23 (17) | C32—C33—C34—C30 | −0.1 (2) |
N1—C15—C16—C24 | −82.12 (14) | Fe1—C33—C34—C30 | −59.91 (14) |
C14—C15—C16—C24 | 160.32 (14) | C32—C33—C34—Fe1 | 59.86 (15) |
N2—C16—C17—C18 | 85.38 (16) | S1—C13—N1—C15 | 31.86 (16) |
C15—C16—C17—C18 | −153.19 (13) | S1—C13—N1—C12 | −98.21 (16) |
C24—C16—C17—C18 | −33.38 (18) | C16—C15—N1—C13 | −168.36 (13) |
N2—C16—C17—C12 | −149.19 (12) | C14—C15—N1—C13 | −44.33 (18) |
C15—C16—C17—C12 | −27.75 (15) | C16—C15—N1—C12 | −34.03 (15) |
C24—C16—C17—C12 | 92.05 (14) | C14—C15—N1—C12 | 90.01 (16) |
N1—C12—C17—C18 | 132.57 (13) | C10—C12—N1—C13 | 19.8 (2) |
C10—C12—C17—C18 | −97.87 (16) | C17—C12—N1—C13 | 146.48 (15) |
C1—C12—C17—C18 | 16.87 (18) | C1—C12—N1—C13 | −94.53 (17) |
N1—C12—C17—C16 | 7.54 (15) | C10—C12—N1—C15 | −109.86 (16) |
C10—C12—C17—C16 | 137.10 (14) | C17—C12—N1—C15 | 16.86 (16) |
C1—C12—C17—C16 | −108.16 (14) | C1—C12—N1—C15 | 135.85 (13) |
C16—C17—C18—C23 | 8.6 (2) | C15—C16—N2—O4 | 22.38 (19) |
C12—C17—C18—C23 | −111.04 (17) | C17—C16—N2—O4 | 139.20 (15) |
C16—C17—C18—C19 | −172.07 (15) | C24—C16—N2—O4 | −100.16 (16) |
C12—C17—C18—C19 | 68.33 (19) | C15—C16—N2—O3 | −161.40 (13) |
C23—C18—C19—C20 | 0.4 (3) | C17—C16—N2—O3 | −44.58 (18) |
C17—C18—C19—C20 | −178.95 (17) | C24—C16—N2—O3 | 76.06 (16) |
C18—C19—C20—C21 | 0.2 (3) | C18—C23—O2—C24 | 26.5 (2) |
C19—C20—C21—C22 | −0.5 (3) | C22—C23—O2—C24 | −155.38 (15) |
C20—C21—C22—C23 | 0.1 (3) | C25—C24—O2—C23 | −177.50 (13) |
C19—C18—C23—O2 | 177.22 (15) | C16—C24—O2—C23 | −52.13 (18) |
C17—C18—C23—O2 | −3.4 (2) | C15—C14—S1—C13 | −14.50 (13) |
C19—C18—C23—C22 | −0.8 (3) | N1—C13—S1—C14 | −8.95 (14) |
C17—C18—C23—C22 | 178.54 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13A···O3i | 0.97 | 2.50 | 3.417 (3) | 157 |
C20—H20···O4ii | 0.93 | 2.59 | 3.440 (3) | 152 |
C24—H24···O1 | 0.98 | 2.51 | 3.301 (3) | 138 |
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x+1/2, −y+1/2, z−1/2. |
C31H24N2O5S | Z = 2 |
Mr = 536.58 | F(000) = 560 |
Triclinic, P1 | Dx = 1.416 Mg m−3 |
a = 11.1123 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.6373 (2) Å | Cell parameters from 5157 reflections |
c = 12.4095 (3) Å | θ = 2.0–26.4° |
α = 117.812 (1)° | µ = 0.18 mm−1 |
β = 110.812 (1)° | T = 293 K |
γ = 95.468 (1)° | Block, colourless |
V = 1258.89 (7) Å3 | 0.22 × 0.18 × 0.10 mm |
Bruker SMART APEXII area-detector diffractometer | 4192 reflections with I > 2σ(I) |
ω and φ scans | Rint = 0.023 |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | θmax = 26.4°, θmin = 2.0° |
Tmin = 0.746, Tmax = 0.845 | h = −13→13 |
18670 measured reflections | k = −14→14 |
5157 independent reflections | l = −15→15 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.105 | w = 1/[σ2(Fo2) + (0.0497P)2 + 0.3546P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
5157 reflections | Δρmax = 0.25 e Å−3 |
353 parameters | Δρmin = −0.29 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 | ||
C1 | 0.16234 (14) | 0.21087 (14) | 1.00050 (14) | 0.0303 (3) | |
C2 | 0.29371 (14) | 0.31519 (15) | 1.06617 (14) | 0.0334 (3) | |
C3 | 0.35025 (16) | 0.44717 (16) | 1.17791 (16) | 0.0426 (4) | |
H3 | 0.3036 | 0.4866 | 1.2273 | 0.051* | |
C4 | 0.48101 (18) | 0.52074 (18) | 1.2151 (2) | 0.0555 (5) | |
H4 | 0.5204 | 0.6108 | 1.2895 | 0.067* | |
C5 | 0.55205 (18) | 0.46379 (19) | 1.1449 (2) | 0.0596 (5) | |
H5 | 0.6383 | 0.5160 | 1.1729 | 0.071* | |
C6 | 0.49749 (16) | 0.32733 (18) | 1.03078 (18) | 0.0466 (4) | |
C7 | 0.55832 (18) | 0.2539 (2) | 0.9491 (2) | 0.0587 (5) | |
H7 | 0.6456 | 0.2956 | 0.9691 | 0.070* | |
C8 | 0.48953 (18) | 0.1227 (2) | 0.8415 (2) | 0.0567 (5) | |
H8 | 0.5320 | 0.0765 | 0.7898 | 0.068* | |
C9 | 0.35631 (16) | 0.05349 (18) | 0.80482 (17) | 0.0456 (4) | |
H9 | 0.3117 | −0.0359 | 0.7297 | 0.055* | |
C10 | 0.29429 (14) | 0.12055 (15) | 0.88192 (15) | 0.0338 (3) | |
C11 | 0.36606 (14) | 0.25606 (15) | 0.99389 (15) | 0.0350 (3) | |
C12 | 0.15158 (13) | 0.08333 (14) | 0.86708 (14) | 0.0296 (3) | |
C17 | 0.04423 (13) | 0.07120 (14) | 0.73580 (14) | 0.0300 (3) | |
H17 | 0.0788 | 0.0420 | 0.6679 | 0.036* | |
C18 | 0.01547 (14) | 0.20175 (15) | 0.76059 (14) | 0.0330 (3) | |
C19 | 0.10115 (16) | 0.30340 (17) | 0.76795 (17) | 0.0422 (4) | |
H19 | 0.1760 | 0.2885 | 0.7529 | 0.051* | |
C20 | 0.07654 (18) | 0.42587 (18) | 0.7973 (2) | 0.0537 (5) | |
H20 | 0.1339 | 0.4925 | 0.8008 | 0.064* | |
C21 | −0.03321 (18) | 0.44951 (18) | 0.8216 (2) | 0.0539 (5) | |
H21 | −0.0484 | 0.5331 | 0.8437 | 0.065* | |
C22 | −0.12025 (16) | 0.34983 (16) | 0.81319 (17) | 0.0464 (4) | |
H22 | −0.1941 | 0.3659 | 0.8300 | 0.056* | |
C23 | −0.09723 (14) | 0.22551 (15) | 0.77958 (15) | 0.0358 (3) | |
C24 | −0.17388 (14) | 0.00433 (14) | 0.75027 (14) | 0.0326 (3) | |
H24 | −0.1306 | 0.0227 | 0.8431 | 0.039* | |
C25 | −0.31406 (14) | −0.09614 (14) | 0.67748 (14) | 0.0320 (3) | |
C30 | −0.41836 (15) | −0.10188 (16) | 0.56946 (16) | 0.0396 (3) | |
H30 | −0.4010 | −0.0438 | 0.5410 | 0.047* | |
C29 | −0.54640 (16) | −0.19207 (17) | 0.50438 (17) | 0.0453 (4) | |
H29 | −0.6151 | −0.1937 | 0.4332 | 0.054* | |
C28 | −0.57380 (15) | −0.28045 (17) | 0.54407 (16) | 0.0426 (4) | |
C31 | −0.7326 (2) | −0.4772 (2) | 0.4878 (2) | 0.0693 (6) | |
H31A | −0.6753 | −0.5323 | 0.4670 | 0.104* | |
H31B | −0.8259 | −0.5322 | 0.4271 | 0.104* | |
H31C | −0.7160 | −0.4419 | 0.5806 | 0.104* | |
C27 | −0.47286 (17) | −0.27538 (18) | 0.65139 (18) | 0.0481 (4) | |
H27 | −0.4906 | −0.3335 | 0.6797 | 0.058* | |
C26 | −0.34419 (15) | −0.18291 (18) | 0.71723 (16) | 0.0420 (4) | |
H26 | −0.2765 | −0.1795 | 0.7902 | 0.050* | |
C16 | −0.07894 (14) | −0.04652 (14) | 0.68327 (13) | 0.0313 (3) | |
C15 | −0.01600 (15) | −0.14060 (14) | 0.72294 (15) | 0.0355 (3) | |
H15 | −0.0812 | −0.1964 | 0.7299 | 0.043* | |
C14 | 0.04383 (17) | −0.23249 (16) | 0.63316 (17) | 0.0456 (4) | |
H14A | 0.0794 | −0.1880 | 0.5964 | 0.055* | |
H14B | −0.0246 | −0.3194 | 0.5579 | 0.055* | |
C13 | 0.18494 (18) | −0.11019 (17) | 0.90177 (18) | 0.0451 (4) | |
H13A | 0.1559 | −0.1419 | 0.9510 | 0.054* | |
H13B | 0.2769 | −0.0476 | 0.9621 | 0.054* | |
N1 | 0.09591 (12) | −0.04224 (12) | 0.85801 (12) | 0.0338 (3) | |
N2 | −0.16219 (13) | −0.11755 (14) | 0.53086 (13) | 0.0409 (3) | |
O1 | 0.07738 (10) | 0.21597 (11) | 1.04066 (10) | 0.0397 (3) | |
O2 | −0.19534 (11) | 0.12778 (11) | 0.76151 (12) | 0.0450 (3) | |
O3 | −0.17443 (13) | −0.04707 (14) | 0.48225 (12) | 0.0574 (3) | |
O4 | −0.21819 (13) | −0.24098 (12) | 0.46534 (12) | 0.0571 (3) | |
O5 | −0.70369 (12) | −0.36725 (14) | 0.47129 (14) | 0.0640 (4) | |
S1 | 0.17845 (6) | −0.25726 (5) | 0.74712 (6) | 0.06168 (16) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0301 (7) | 0.0321 (7) | 0.0293 (7) | 0.0130 (6) | 0.0119 (6) | 0.0175 (6) |
C2 | 0.0312 (7) | 0.0345 (8) | 0.0328 (7) | 0.0120 (6) | 0.0114 (6) | 0.0187 (6) |
C3 | 0.0398 (8) | 0.0347 (8) | 0.0419 (8) | 0.0123 (7) | 0.0141 (7) | 0.0157 (7) |
C4 | 0.0441 (9) | 0.0352 (9) | 0.0585 (11) | 0.0029 (7) | 0.0138 (8) | 0.0135 (8) |
C5 | 0.0361 (9) | 0.0491 (11) | 0.0702 (12) | −0.0016 (8) | 0.0169 (8) | 0.0235 (10) |
C6 | 0.0313 (8) | 0.0496 (10) | 0.0552 (10) | 0.0094 (7) | 0.0171 (7) | 0.0280 (8) |
C7 | 0.0335 (9) | 0.0705 (13) | 0.0716 (12) | 0.0135 (9) | 0.0282 (9) | 0.0353 (11) |
C8 | 0.0428 (9) | 0.0705 (13) | 0.0626 (11) | 0.0248 (9) | 0.0348 (9) | 0.0309 (10) |
C9 | 0.0397 (8) | 0.0479 (10) | 0.0469 (9) | 0.0175 (7) | 0.0242 (7) | 0.0198 (8) |
C10 | 0.0295 (7) | 0.0388 (8) | 0.0360 (7) | 0.0137 (6) | 0.0151 (6) | 0.0215 (7) |
C11 | 0.0291 (7) | 0.0377 (8) | 0.0383 (8) | 0.0115 (6) | 0.0133 (6) | 0.0219 (7) |
C12 | 0.0293 (7) | 0.0296 (7) | 0.0312 (7) | 0.0114 (6) | 0.0147 (6) | 0.0162 (6) |
C17 | 0.0293 (7) | 0.0315 (7) | 0.0285 (7) | 0.0087 (6) | 0.0140 (5) | 0.0153 (6) |
C18 | 0.0320 (7) | 0.0331 (7) | 0.0294 (7) | 0.0081 (6) | 0.0090 (6) | 0.0175 (6) |
C19 | 0.0386 (8) | 0.0416 (9) | 0.0494 (9) | 0.0092 (7) | 0.0171 (7) | 0.0292 (8) |
C20 | 0.0474 (10) | 0.0427 (10) | 0.0685 (12) | 0.0070 (8) | 0.0164 (9) | 0.0366 (9) |
C21 | 0.0479 (10) | 0.0341 (9) | 0.0647 (11) | 0.0123 (7) | 0.0108 (8) | 0.0266 (8) |
C22 | 0.0367 (8) | 0.0380 (9) | 0.0515 (9) | 0.0139 (7) | 0.0124 (7) | 0.0200 (8) |
C23 | 0.0308 (7) | 0.0315 (7) | 0.0349 (7) | 0.0068 (6) | 0.0088 (6) | 0.0157 (6) |
C24 | 0.0317 (7) | 0.0324 (7) | 0.0315 (7) | 0.0098 (6) | 0.0152 (6) | 0.0151 (6) |
C25 | 0.0299 (7) | 0.0331 (7) | 0.0316 (7) | 0.0105 (6) | 0.0142 (6) | 0.0162 (6) |
C30 | 0.0368 (8) | 0.0396 (8) | 0.0413 (8) | 0.0091 (7) | 0.0123 (7) | 0.0255 (7) |
C29 | 0.0347 (8) | 0.0464 (9) | 0.0422 (9) | 0.0078 (7) | 0.0054 (7) | 0.0245 (8) |
C28 | 0.0327 (8) | 0.0390 (8) | 0.0441 (9) | 0.0042 (6) | 0.0141 (7) | 0.0176 (7) |
C31 | 0.0636 (12) | 0.0463 (11) | 0.0810 (14) | −0.0031 (9) | 0.0374 (11) | 0.0227 (10) |
C27 | 0.0418 (9) | 0.0533 (10) | 0.0589 (10) | 0.0097 (8) | 0.0215 (8) | 0.0389 (9) |
C26 | 0.0352 (8) | 0.0543 (10) | 0.0431 (8) | 0.0129 (7) | 0.0145 (7) | 0.0334 (8) |
C16 | 0.0310 (7) | 0.0304 (7) | 0.0269 (7) | 0.0069 (6) | 0.0132 (6) | 0.0118 (6) |
C15 | 0.0376 (8) | 0.0282 (7) | 0.0392 (8) | 0.0090 (6) | 0.0203 (6) | 0.0151 (6) |
C14 | 0.0523 (10) | 0.0332 (8) | 0.0487 (9) | 0.0159 (7) | 0.0277 (8) | 0.0163 (7) |
C13 | 0.0530 (10) | 0.0438 (9) | 0.0514 (9) | 0.0249 (8) | 0.0262 (8) | 0.0311 (8) |
N1 | 0.0363 (6) | 0.0312 (6) | 0.0373 (6) | 0.0129 (5) | 0.0174 (5) | 0.0198 (5) |
N2 | 0.0362 (7) | 0.0433 (8) | 0.0306 (6) | 0.0059 (6) | 0.0147 (5) | 0.0126 (6) |
O1 | 0.0362 (5) | 0.0429 (6) | 0.0366 (6) | 0.0130 (5) | 0.0201 (5) | 0.0162 (5) |
O2 | 0.0356 (6) | 0.0318 (6) | 0.0648 (7) | 0.0117 (5) | 0.0261 (5) | 0.0214 (5) |
O3 | 0.0608 (8) | 0.0663 (8) | 0.0370 (6) | 0.0120 (6) | 0.0136 (6) | 0.0296 (6) |
O4 | 0.0537 (7) | 0.0416 (7) | 0.0383 (6) | −0.0039 (6) | 0.0137 (5) | 0.0034 (5) |
O5 | 0.0394 (6) | 0.0582 (8) | 0.0674 (8) | −0.0082 (6) | 0.0094 (6) | 0.0297 (7) |
S1 | 0.0781 (4) | 0.0513 (3) | 0.0716 (3) | 0.0425 (3) | 0.0426 (3) | 0.0342 (3) |
C1—O1 | 1.2085 (17) | C22—H22 | 0.9300 |
C1—C2 | 1.471 (2) | C23—O2 | 1.3728 (18) |
C1—C12 | 1.5783 (19) | C24—O2 | 1.4291 (18) |
C2—C3 | 1.373 (2) | C24—C25 | 1.5090 (19) |
C2—C11 | 1.402 (2) | C24—C16 | 1.5612 (19) |
C3—C4 | 1.405 (2) | C24—H24 | 0.9800 |
C3—H3 | 0.9300 | C25—C26 | 1.376 (2) |
C4—C5 | 1.367 (3) | C25—C30 | 1.394 (2) |
C4—H4 | 0.9300 | C30—C29 | 1.373 (2) |
C5—C6 | 1.415 (3) | C30—H30 | 0.9300 |
C5—H5 | 0.9300 | C29—C28 | 1.383 (2) |
C6—C11 | 1.404 (2) | C29—H29 | 0.9300 |
C6—C7 | 1.415 (3) | C28—O5 | 1.3652 (18) |
C7—C8 | 1.359 (3) | C28—C27 | 1.374 (2) |
C7—H7 | 0.9300 | C31—O5 | 1.413 (2) |
C8—C9 | 1.414 (2) | C31—H31A | 0.9600 |
C8—H8 | 0.9300 | C31—H31B | 0.9600 |
C9—C10 | 1.369 (2) | C31—H31C | 0.9600 |
C9—H9 | 0.9300 | C27—C26 | 1.388 (2) |
C10—C11 | 1.408 (2) | C27—H27 | 0.9300 |
C10—C12 | 1.5242 (19) | C26—H26 | 0.9300 |
C12—N1 | 1.4682 (18) | C16—N2 | 1.5061 (18) |
C12—C17 | 1.5714 (19) | C16—C15 | 1.528 (2) |
C17—C18 | 1.494 (2) | C15—N1 | 1.4572 (19) |
C17—C16 | 1.5331 (19) | C15—C14 | 1.542 (2) |
C17—H17 | 0.9800 | C15—H15 | 0.9800 |
C18—C23 | 1.384 (2) | C14—S1 | 1.8111 (18) |
C18—C19 | 1.392 (2) | C14—H14A | 0.9700 |
C19—C20 | 1.378 (2) | C14—H14B | 0.9700 |
C19—H19 | 0.9300 | C13—N1 | 1.438 (2) |
C20—C21 | 1.379 (3) | C13—S1 | 1.8521 (17) |
C20—H20 | 0.9300 | C13—H13A | 0.9700 |
C21—C22 | 1.376 (2) | C13—H13B | 0.9700 |
C21—H21 | 0.9300 | N2—O3 | 1.2164 (18) |
C22—C23 | 1.384 (2) | N2—O4 | 1.2215 (17) |
O1—C1—C2 | 127.79 (13) | O2—C24—C25 | 105.19 (11) |
O1—C1—C12 | 124.36 (12) | O2—C24—C16 | 113.86 (11) |
C2—C1—C12 | 107.80 (11) | C25—C24—C16 | 114.99 (11) |
C3—C2—C11 | 120.59 (14) | O2—C24—H24 | 107.5 |
C3—C2—C1 | 132.13 (14) | C25—C24—H24 | 107.5 |
C11—C2—C1 | 107.27 (12) | C16—C24—H24 | 107.5 |
C2—C3—C4 | 117.80 (16) | C26—C25—C30 | 117.72 (13) |
C2—C3—H3 | 121.1 | C26—C25—C24 | 121.29 (13) |
C4—C3—H3 | 121.1 | C30—C25—C24 | 120.97 (13) |
C5—C4—C3 | 121.91 (16) | C29—C30—C25 | 120.97 (14) |
C5—C4—H4 | 119.0 | C29—C30—H30 | 119.5 |
C3—C4—H4 | 119.0 | C25—C30—H30 | 119.5 |
C4—C5—C6 | 121.62 (16) | C30—C29—C28 | 120.37 (15) |
C4—C5—H5 | 119.2 | C30—C29—H29 | 119.8 |
C6—C5—H5 | 119.2 | C28—C29—H29 | 119.8 |
C11—C6—C5 | 115.69 (16) | O5—C28—C27 | 124.78 (15) |
C11—C6—C7 | 116.01 (16) | O5—C28—C29 | 115.62 (15) |
C5—C6—C7 | 128.30 (16) | C27—C28—C29 | 119.60 (14) |
C8—C7—C6 | 120.19 (16) | O5—C31—H31A | 109.5 |
C8—C7—H7 | 119.9 | O5—C31—H31B | 109.5 |
C6—C7—H7 | 119.9 | H31A—C31—H31B | 109.5 |
C7—C8—C9 | 122.90 (16) | O5—C31—H31C | 109.5 |
C7—C8—H8 | 118.6 | H31A—C31—H31C | 109.5 |
C9—C8—H8 | 118.6 | H31B—C31—H31C | 109.5 |
C10—C9—C8 | 118.72 (16) | C28—C27—C26 | 119.50 (15) |
C10—C9—H9 | 120.6 | C28—C27—H27 | 120.2 |
C8—C9—H9 | 120.6 | C26—C27—H27 | 120.2 |
C9—C10—C11 | 118.31 (14) | C25—C26—C27 | 121.81 (14) |
C9—C10—C12 | 132.99 (14) | C25—C26—H26 | 119.1 |
C11—C10—C12 | 108.51 (12) | C27—C26—H26 | 119.1 |
C2—C11—C6 | 122.37 (14) | N2—C16—C15 | 111.92 (12) |
C2—C11—C10 | 113.76 (13) | N2—C16—C17 | 110.50 (11) |
C6—C11—C10 | 123.87 (14) | C15—C16—C17 | 103.66 (11) |
N1—C12—C10 | 120.51 (12) | N2—C16—C24 | 107.57 (11) |
N1—C12—C17 | 104.32 (11) | C15—C16—C24 | 111.11 (11) |
C10—C12—C17 | 110.66 (11) | C17—C16—C24 | 112.14 (11) |
N1—C12—C1 | 108.87 (11) | N1—C15—C16 | 101.78 (11) |
C10—C12—C1 | 101.87 (11) | N1—C15—C14 | 107.69 (12) |
C17—C12—C1 | 110.56 (11) | C16—C15—C14 | 116.88 (13) |
C18—C17—C16 | 114.61 (12) | N1—C15—H15 | 110.0 |
C18—C17—C12 | 114.00 (11) | C16—C15—H15 | 110.0 |
C16—C17—C12 | 103.47 (11) | C14—C15—H15 | 110.0 |
C18—C17—H17 | 108.1 | C15—C14—S1 | 104.77 (11) |
C16—C17—H17 | 108.1 | C15—C14—H14A | 110.8 |
C12—C17—H17 | 108.1 | S1—C14—H14A | 110.8 |
C23—C18—C19 | 118.15 (14) | C15—C14—H14B | 110.8 |
C23—C18—C17 | 120.18 (13) | S1—C14—H14B | 110.8 |
C19—C18—C17 | 121.66 (14) | H14A—C14—H14B | 108.9 |
C20—C19—C18 | 120.87 (16) | N1—C13—S1 | 107.70 (11) |
C20—C19—H19 | 119.6 | N1—C13—H13A | 110.2 |
C18—C19—H19 | 119.6 | S1—C13—H13A | 110.2 |
C19—C20—C21 | 119.93 (16) | N1—C13—H13B | 110.2 |
C19—C20—H20 | 120.0 | S1—C13—H13B | 110.2 |
C21—C20—H20 | 120.0 | H13A—C13—H13B | 108.5 |
C22—C21—C20 | 120.20 (16) | C13—N1—C15 | 110.12 (12) |
C22—C21—H21 | 119.9 | C13—N1—C12 | 120.18 (12) |
C20—C21—H21 | 119.9 | C15—N1—C12 | 111.07 (11) |
C21—C22—C23 | 119.54 (16) | O3—N2—O4 | 124.37 (14) |
C21—C22—H22 | 120.2 | O3—N2—C16 | 117.71 (13) |
C23—C22—H22 | 120.2 | O4—N2—C16 | 117.82 (13) |
O2—C23—C18 | 123.07 (13) | C23—O2—C24 | 121.41 (11) |
O2—C23—C22 | 115.68 (14) | C28—O5—C31 | 118.60 (15) |
C18—C23—C22 | 121.20 (14) | C14—S1—C13 | 92.72 (7) |
O1—C1—C2—C3 | −7.6 (3) | O2—C24—C25—C26 | −138.70 (14) |
C12—C1—C2—C3 | 174.87 (16) | C16—C24—C25—C26 | 95.21 (17) |
O1—C1—C2—C11 | 171.08 (14) | O2—C24—C25—C30 | 39.81 (17) |
C12—C1—C2—C11 | −6.50 (15) | C16—C24—C25—C30 | −86.28 (17) |
C11—C2—C3—C4 | 1.2 (2) | C26—C25—C30—C29 | −0.6 (2) |
C1—C2—C3—C4 | 179.63 (16) | C24—C25—C30—C29 | −179.14 (14) |
C2—C3—C4—C5 | −1.1 (3) | C25—C30—C29—C28 | −0.8 (3) |
C3—C4—C5—C6 | 0.0 (3) | C30—C29—C28—O5 | −179.01 (16) |
C4—C5—C6—C11 | 0.9 (3) | C30—C29—C28—C27 | 1.5 (3) |
C4—C5—C6—C7 | −179.3 (2) | O5—C28—C27—C26 | 179.69 (16) |
C11—C6—C7—C8 | 0.5 (3) | C29—C28—C27—C26 | −0.9 (3) |
C5—C6—C7—C8 | −179.3 (2) | C30—C25—C26—C27 | 1.2 (2) |
C6—C7—C8—C9 | 0.5 (3) | C24—C25—C26—C27 | 179.76 (15) |
C7—C8—C9—C10 | −1.0 (3) | C28—C27—C26—C25 | −0.5 (3) |
C8—C9—C10—C11 | 0.5 (2) | C18—C17—C16—N2 | 82.79 (14) |
C8—C9—C10—C12 | 174.67 (16) | C12—C17—C16—N2 | −152.48 (11) |
C3—C2—C11—C6 | −0.2 (2) | C18—C17—C16—C15 | −157.15 (11) |
C1—C2—C11—C6 | −179.06 (14) | C12—C17—C16—C15 | −32.42 (13) |
C3—C2—C11—C10 | −179.84 (14) | C18—C17—C16—C24 | −37.21 (16) |
C1—C2—C11—C10 | 1.34 (17) | C12—C17—C16—C24 | 87.52 (13) |
C5—C6—C11—C2 | −0.8 (2) | O2—C24—C16—N2 | −79.34 (14) |
C7—C6—C11—C2 | 179.40 (16) | C25—C24—C16—N2 | 42.14 (16) |
C5—C6—C11—C10 | 178.78 (16) | O2—C24—C16—C15 | 157.84 (11) |
C7—C6—C11—C10 | −1.0 (2) | C25—C24—C16—C15 | −80.67 (15) |
C9—C10—C11—C2 | −179.85 (14) | O2—C24—C16—C17 | 42.35 (16) |
C12—C10—C11—C2 | 4.61 (17) | C25—C24—C16—C17 | 163.83 (12) |
C9—C10—C11—C6 | 0.6 (2) | N2—C16—C15—N1 | 158.74 (11) |
C12—C10—C11—C6 | −174.99 (14) | C17—C16—C15—N1 | 39.65 (13) |
C9—C10—C12—N1 | 56.9 (2) | C24—C16—C15—N1 | −80.99 (13) |
C11—C10—C12—N1 | −128.44 (13) | N2—C16—C15—C14 | 41.75 (17) |
C9—C10—C12—C17 | −65.0 (2) | C17—C16—C15—C14 | −77.34 (15) |
C11—C10—C12—C17 | 109.62 (13) | C24—C16—C15—C14 | 162.02 (12) |
C9—C10—C12—C1 | 177.43 (17) | N1—C15—C14—S1 | 37.43 (14) |
C11—C10—C12—C1 | −7.94 (15) | C16—C15—C14—S1 | 151.13 (11) |
O1—C1—C12—N1 | −40.63 (18) | S1—C13—N1—C15 | 30.38 (15) |
C2—C1—C12—N1 | 137.05 (11) | S1—C13—N1—C12 | −100.60 (13) |
O1—C1—C12—C10 | −168.95 (13) | C16—C15—N1—C13 | −168.37 (12) |
C2—C1—C12—C10 | 8.73 (14) | C14—C15—N1—C13 | −44.91 (16) |
O1—C1—C12—C17 | 73.41 (17) | C16—C15—N1—C12 | −32.75 (14) |
C2—C1—C12—C17 | −108.91 (12) | C14—C15—N1—C12 | 90.71 (14) |
N1—C12—C17—C18 | 138.20 (12) | C10—C12—N1—C13 | 18.04 (19) |
C10—C12—C17—C18 | −90.79 (14) | C17—C12—N1—C13 | 143.01 (13) |
C1—C12—C17—C18 | 21.31 (16) | C1—C12—N1—C13 | −98.94 (14) |
N1—C12—C17—C16 | 13.06 (13) | C10—C12—N1—C15 | −112.52 (14) |
C10—C12—C17—C16 | 144.08 (11) | C17—C12—N1—C15 | 12.44 (14) |
C1—C12—C17—C16 | −103.82 (12) | C1—C12—N1—C15 | 130.49 (12) |
C16—C17—C18—C23 | 20.89 (18) | C15—C16—N2—O3 | −152.92 (13) |
C12—C17—C18—C23 | −98.09 (15) | C17—C16—N2—O3 | −37.95 (17) |
C16—C17—C18—C19 | −160.37 (13) | C24—C16—N2—O3 | 84.76 (15) |
C12—C17—C18—C19 | 80.65 (17) | C15—C16—N2—O4 | 30.56 (18) |
C23—C18—C19—C20 | 1.9 (2) | C17—C16—N2—O4 | 145.53 (13) |
C17—C18—C19—C20 | −176.89 (15) | C24—C16—N2—O4 | −91.76 (15) |
C18—C19—C20—C21 | 0.8 (3) | C18—C23—O2—C24 | 13.6 (2) |
C19—C20—C21—C22 | −1.7 (3) | C22—C23—O2—C24 | −168.94 (13) |
C20—C21—C22—C23 | −0.3 (3) | C25—C24—O2—C23 | −157.98 (12) |
C19—C18—C23—O2 | 173.50 (14) | C16—C24—O2—C23 | −31.20 (18) |
C17—C18—C23—O2 | −7.7 (2) | C27—C28—O5—C31 | −12.7 (3) |
C19—C18—C23—C22 | −3.9 (2) | C29—C28—O5—C31 | 167.94 (17) |
C17—C18—C23—C22 | 174.92 (14) | C15—C14—S1—C13 | −17.28 (12) |
C21—C22—C23—O2 | −174.43 (15) | N1—C13—S1—C14 | −6.37 (12) |
C21—C22—C23—C18 | 3.1 (2) |
Cg1 and Cg2 are the centroids of the C25–C30 and C2–C11 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17···O3i | 0.98 | 2.47 | 3.412 (2) | 161 |
C24—H24···O1 | 0.98 | 2.50 | 3.178 (19) | 126 |
C8—H8···Cg1ii | 0.93 | 2.82 | 3.759 (2) | 148 |
C27—H27···Cg2iii | 0.93 | 2.79 | 3.720 (3) | 149 |
Symmetry codes: (i) −x, −y, −z+1; (ii) x+1, y, z; (iii) −x, −y, −z+2. |
Acknowledgements
VV and DV thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. VV thanks the DBT, Government of India, for a fellowship.
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