research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 72| Part 8| August 2016| Pages 1126-1129
https://doi.org/10.1107/S2056989016011336

Crystal structures of two substituted thia­zolidine derivatives

CROSSMARK_Color_square_no_text.svg
Vijayan Viswanathan,a Naga Siva Rao,b Raghavachary Raghunathanb and Devadasan Velmurugana*

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

Edited by R. F. Baggio, Comisión Nacional de Energía Atómica, Argentina (Received 3 June 2016; accepted 12 July 2016; online 19 July 2016)

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 envelope conformation 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.

CCDC references: 1023737; 1023726

Similar articles

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[Fun, H.-K., Hemamalini, M., Shanmugavelan, P., Ponnuswamy, A. & Jagatheesan, R. (2011). Acta Cryst. E67, o2706.]). Thia­zolidine derivatives have attracted continuous inter­est over the years because of their varied biological activities (Shih et al., 2015[Shih, M. H., Xu, Y. Y., Yang, Y. S. & Lin, G. L. (2015). Molecules, 20, 6520-6532.]). 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[Čačić, M., Molnar, M., Šarkanj, B., Has-Schön, E. & Rajković, V. (2010). Molecules, 15, 6795-6809.]). 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[Samadhiya, P., Sharma, R., Srivastava, S. K. & Srivastava, S. D. (2012). Leonardo J. Sci. 20, 37-58.]), anti­convulsant (Pandey et al., 2011[Pandey, Y., Sharma, P. K., Kumar, N. & Singh, A. (2011). Int. J. Pharm. Tech Res. 3, 980-985.]), anti­cancer and anti-oxidant, and also has inter­esting anti­microbial activity (influenza). In addition, anti­diabetic properties (Majed & Abid, 2015[Majed, A. A. & Abid, D. S. (2015). Basrah J. Sci. 33, 101-117.]) have been reported. Thia­zolidine derivatives exhibit anti-HIV, anti­tuberculotic (Fun et al., 2011[Fun, H.-K., Hemamalini, M., Shanmugavelan, P., Ponnuswamy, A. & Jagatheesan, R. (2011). Acta Cryst. E67, o2706.]), herbicidal, anti­neoplastic, hypolipidemic and anti-inflammatory activities (Vennila et al., 2011[Vennila, J. P., Thiruvadigal, D. J., Kavitha, H. P., Chakkaravarthi, G. & Manivannan, V. (2011). Acta Cryst. E67, o1902.]). 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 peptidoglycan, non-nucleoside inhibitors of HIV–RT and anti-histaminic agents (Čačić et al., 2010[Čačić, M., Molnar, M., Šarkanj, B., Has-Schön, E. & Rajković, V. (2010). Molecules, 15, 6795-6809.]).

[Scheme 1]
[Scheme 2]

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)[link] (Fig. 1[link]), 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)[link] (Fig. 2[link]), 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)[link] and an envelope conformation with atom C15 as the flap in (II)[link]. 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)[link] and (II)[link], 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 envelope conformation, the flaps being atom C24 in (I)[link], displaced by −0.5585 (1) Å, and atom C16 in (II)[link], displaced by 0.4076 (3) Å.

[Figure 1]
Figure 1
The mol­ecular structure of (I)[link], showing the atom labelling and displacement ellipsoids drawn at 30% probability level. The C—H⋯O contact is shown as a thin dashed line.
[Figure 2]
Figure 2
The mol­ecular structure of (II)[link], showing the atom labelling and displacement ellipsoids drawn at 30% probability level. The C—H⋯O contact is shown as a thin dashed line.

The pyrrolidine and the chromane ring systems subtend dihedral angles of 74.94 (8) and 67.68 (7)° in (I)[link] and (II)[link], respectively. In (I)[link], 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)[link], 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)[link] and (II)[link], respectively.

In both compounds, an intra­molecular C—H⋯O hydrogen bond forms an S(7) ring motif (Figs. 1[link] and 2[link]; Tables 1[link] and 2[link]).

Table 1
Hydrogen-bond geometry (Å, °) for (I)[link]

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+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Table 2
Hydrogen-bond geometry (Å, °) for (II)[link]

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.

3. Supra­molecular features

In the crystal of (I)[link], mol­ecules are linked via C—H⋯O hydrogen bonds along [001] and [100] (Fig. 3[link] and Table 1[link]), generating planes parallel to (010) with embedded R44(29) ring motifs. In the crystal of (II)[link], mol­ecules are linked via C—H⋯O hydrogen bonds, forming dimers with an [R_{2}^{2}](10) ring motif, as shown in Fig. 4[link] and Table 2[link]. C—H⋯π inter­actions link the mol­ecules in a head-to-tail fashion, forming chains extending along [100] (Fig. 5[link]).

[Figure 3]
Figure 3
The crystal packing of (I)[link]. Note that the C—H⋯O hydrogen bonds (shown as dashed lines) run along [001] and [100] and generate an R44(29) ring motif. H atoms not involved in hydrogen bonds have been excluded for clarity.
[Figure 4]
Figure 4
The crystal packing of (II)[link], showing the [R_{2}^{2}](10) ring motif. H atoms not involved in hydrogen bonds have been excluded for clarity.
[Figure 5]
Figure 5
The compound (II)[link] showing the C—H⋯π inter­actions linking mol­ecules in a head-to-tail fashion, forming chains running along the a axis. H atoms not involved in hydrogen bonds are omitted for clarity.

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)[link], or 2-(4-meth­oxy­phen­yl)-3-nitro-2H-chromene (1 mmol) for compound (II)[link]. 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 column chromatography using hexa­ne/EtOAc (8:2) as eluent [Yields: 91% for (I)[link], 88% for (II)].

5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3[link]. 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.

Table 3
Experimental details

  (I) (II)
Crystal data
Chemical formula [Fe(C5H5)(C29H21N2O4S)] C31H24N2O5S
Mr 614.48 536.58
Crystal system, space group Monoclinic, P21/n Triclinic, P[\overline{1}]
Temperature (K) 293 293
a, b, c (Å) 11.782 (5), 16.741 (5), 14.147 (5) 11.1123 (5), 11.6373 (2), 12.4095 (3)
α, β, γ (°) 90, 98.013 (5), 90 117.812 (1), 110.812 (1), 95.468 (1)
V (Å3) 2763.1 (17) 1258.89 (7)
Z 4 2
Radiation type Mo Kα Mo Kα
μ (mm−1) 0.67 0.18
Crystal size (mm) 0.19 × 0.16 × 0.11 0.22 × 0.18 × 0.10
 
Data collection
Diffractometer Bruker SMART APEXII area-detector Bruker SMART APEXII area-detector
Absorption correction Multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.746, 0.845 0.746, 0.845
No. of measured, independent and observed [I > 2σ(I)] reflections 25994, 6900, 5281 18670, 5157, 4192
Rint 0.028 0.023
(sin θ/λ)max (Å−1) 0.668 0.626
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.097, 1.03 0.037, 0.105, 1.04
No. of reflections 6900 5157
No. of parameters 379 353
H-atom treatment H-atom parameters constrained H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.29, −0.33 0.25, −0.29
Computer programs: APEX2 and SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

CCDC references: 1023737; 1023726

Crystal structure: contains datablocks global, I, II. DOI: https://doi.org/10.1107/S2056989016011336/bg2588sup1.cif

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

checkCIF report


Computing details top

For both compounds, data collection: APEX2 (Bruker, 2008); cell refinement: 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).

(I) 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 top
Crystal data top
[Fe(C5H5)(C29H21N2O4S)]F(000) = 1272
Mr = 614.48Dx = 1.477 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 11.782 (5) ÅCell parameters from 6900 reflections
b = 16.741 (5) Åθ = 1.9–28.3°
c = 14.147 (5) ŵ = 0.67 mm−1
β = 98.013 (5)°T = 293 K
V = 2763.1 (17) Å3Block, colourless
Z = 40.19 × 0.16 × 0.11 mm
Data collection top
Bruker SMART APEXII area-detector
diffractometer		5281 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.028
ω and φ scansθmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)		h = −15→12
Tmin = 0.746, Tmax = 0.845k = −22→20
25994 measured reflectionsl = −16→18
6900 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H-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 reflectionsΔρmax = 0.29 e Å−3
379 parametersΔρmin = −0.33 e Å−3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.17168 (14)0.29715 (10)0.34129 (12)0.0382 (4)
C20.27528 (15)0.26349 (12)0.30982 (13)0.0437 (4)
C30.36894 (17)0.29875 (15)0.27815 (15)0.0580 (5)
H30.37510.35400.27410.070*
C40.45406 (18)0.24843 (19)0.25235 (17)0.0714 (7)
H40.51730.27130.23010.086*
C50.44852 (18)0.16710 (18)0.25835 (16)0.0683 (7)
H50.50810.13630.24120.082*
C60.35397 (17)0.12899 (14)0.29018 (14)0.0536 (5)
C70.3351 (2)0.04678 (15)0.30007 (16)0.0660 (6)
H70.38970.01030.28550.079*
C80.2377 (2)0.02016 (13)0.33066 (17)0.0649 (6)
H80.2277−0.03460.33720.078*
C90.15032 (19)0.07272 (11)0.35320 (15)0.0528 (5)
H90.08340.05260.37200.063*
C100.16661 (15)0.15301 (10)0.34672 (12)0.0397 (4)
C110.26808 (15)0.18037 (11)0.31521 (12)0.0409 (4)
C120.09371 (13)0.22504 (9)0.36526 (11)0.0327 (3)
C130.13859 (17)0.19957 (12)0.54151 (13)0.0478 (4)
H13A0.15020.23510.59610.057*
H13B0.21280.18630.52350.057*
C14−0.06611 (17)0.13300 (11)0.49327 (14)0.0489 (5)
H14A−0.07380.10070.43580.059*
H14B−0.13300.12480.52500.059*
C15−0.05289 (14)0.22215 (9)0.46914 (11)0.0344 (3)
H15−0.07820.25540.51930.041*
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)
H17−0.04500.17110.28100.037*
C18−0.03280 (14)0.27774 (10)0.21409 (11)0.0335 (3)
C190.02668 (16)0.25728 (12)0.13894 (13)0.0445 (4)
H190.06990.21060.14260.053*
C200.02230 (19)0.30546 (14)0.05904 (14)0.0562 (5)
H200.06210.29110.00930.067*
C21−0.04142 (19)0.37487 (13)0.05351 (13)0.0556 (5)
H21−0.04390.40750.00000.067*
C22−0.10152 (17)0.39641 (11)0.12664 (12)0.0462 (4)
H22−0.14450.44320.12280.055*
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)
H24−0.05180.36740.39300.037*
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)
H26−0.10900.42220.55450.065*
C27−0.2915 (2)0.43003 (14)0.55249 (15)0.0691 (7)
H27−0.30030.45790.61190.083*
C28−0.3806 (2)0.40483 (13)0.48430 (18)0.0621 (6)
H28−0.46250.41140.48780.074*
C29−0.33282 (16)0.36859 (11)0.40861 (16)0.0476 (4)
H29−0.37590.34540.35080.057*
C30−0.1999 (2)0.54692 (11)0.33192 (16)0.0600 (6)
H30−0.13250.52990.30370.072*
C31−0.1986 (2)0.59003 (12)0.41768 (18)0.0629 (6)
H31−0.13010.60780.45980.075*
C32−0.3126 (2)0.60257 (11)0.43236 (16)0.0586 (6)
H32−0.33770.63050.48670.070*
C33−0.3842 (2)0.56757 (12)0.35621 (16)0.0595 (5)
H33−0.46820.56710.34770.071*
C34−0.3144 (2)0.53302 (12)0.29394 (14)0.0591 (6)
H34−0.34130.50480.23430.071*
N10.06793 (12)0.23745 (8)0.46323 (9)0.0346 (3)
N2−0.22575 (12)0.21372 (8)0.34208 (11)0.0363 (3)
O10.14788 (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)
S10.06376 (5)0.10735 (3)0.57181 (4)0.06071 (16)
Fe1−0.27986 (2)0.48313 (2)0.42494 (2)0.03501 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0313 (9)0.0423 (9)0.0401 (9)−0.0019 (7)0.0014 (7)−0.0009 (7)
C20.0288 (9)0.0600 (11)0.0413 (9)−0.0012 (8)0.0016 (7)−0.0017 (8)
C30.0392 (11)0.0821 (15)0.0526 (12)−0.0127 (10)0.0066 (9)−0.0002 (10)
C40.0352 (11)0.125 (2)0.0563 (13)−0.0084 (13)0.0130 (10)−0.0133 (14)
C50.0345 (11)0.117 (2)0.0537 (13)0.0167 (12)0.0063 (9)−0.0229 (13)
C60.0384 (10)0.0803 (15)0.0400 (10)0.0192 (10)−0.0023 (8)−0.0148 (9)
C70.0633 (15)0.0755 (15)0.0566 (13)0.0355 (12)−0.0007 (11)−0.0184 (11)
C80.0830 (17)0.0436 (11)0.0657 (14)0.0229 (11)0.0015 (13)−0.0096 (9)
C90.0585 (13)0.0423 (10)0.0584 (12)0.0086 (9)0.0105 (10)−0.0052 (9)
C100.0375 (9)0.0413 (9)0.0400 (9)0.0090 (7)0.0044 (7)−0.0042 (7)
C110.0312 (9)0.0562 (11)0.0340 (9)0.0100 (8)−0.0003 (7)−0.0066 (7)
C120.0286 (8)0.0324 (8)0.0369 (8)0.0029 (6)0.0038 (6)−0.0023 (6)
C130.0474 (11)0.0517 (11)0.0411 (10)0.0094 (8)−0.0045 (8)0.0007 (8)
C140.0484 (11)0.0448 (10)0.0539 (11)0.0039 (8)0.0082 (9)0.0155 (8)
C150.0358 (9)0.0373 (8)0.0307 (8)0.0051 (7)0.0072 (7)0.0016 (6)
C160.0268 (8)0.0320 (8)0.0318 (8)0.0013 (6)0.0039 (6)−0.0004 (6)
C170.0284 (8)0.0312 (7)0.0323 (8)0.0007 (6)0.0060 (6)−0.0034 (6)
C180.0308 (8)0.0406 (8)0.0290 (8)−0.0047 (7)0.0039 (6)−0.0044 (6)
C190.0424 (10)0.0546 (11)0.0384 (9)−0.0024 (8)0.0120 (8)−0.0084 (8)
C200.0576 (13)0.0762 (14)0.0389 (10)−0.0099 (11)0.0215 (9)−0.0057 (9)
C210.0658 (14)0.0681 (13)0.0338 (9)−0.0130 (11)0.0101 (9)0.0091 (9)
C220.0532 (12)0.0482 (10)0.0364 (9)−0.0053 (8)0.0029 (8)0.0054 (7)
C230.0352 (9)0.0418 (9)0.0284 (8)−0.0051 (7)0.0045 (6)−0.0022 (6)
C240.0328 (8)0.0317 (8)0.0285 (7)0.0022 (6)0.0045 (6)0.0005 (6)
C250.0406 (9)0.0341 (8)0.0341 (8)0.0090 (7)0.0083 (7)0.0049 (6)
C260.0668 (13)0.0656 (12)0.0300 (9)0.0278 (10)0.0021 (9)0.0005 (8)
C270.100 (2)0.0739 (15)0.0400 (11)0.0418 (14)0.0312 (13)0.0130 (10)
C280.0616 (14)0.0558 (12)0.0778 (16)0.0136 (10)0.0413 (13)0.0157 (11)
C290.0403 (10)0.0371 (9)0.0687 (12)−0.0014 (8)0.0191 (9)−0.0013 (8)
C300.0800 (16)0.0359 (10)0.0717 (14)−0.0013 (10)0.0380 (13)0.0044 (9)
C310.0682 (15)0.0406 (10)0.0811 (16)−0.0106 (10)0.0151 (12)−0.0122 (10)
C320.0757 (15)0.0358 (10)0.0663 (14)0.0118 (9)0.0172 (12)−0.0083 (9)
C330.0657 (14)0.0489 (11)0.0620 (13)0.0194 (10)0.0019 (11)0.0094 (10)
C340.0931 (18)0.0450 (11)0.0387 (10)0.0105 (11)0.0074 (11)0.0085 (8)
N10.0331 (7)0.0372 (7)0.0323 (7)0.0056 (6)0.0005 (6)−0.0015 (5)
N20.0288 (7)0.0346 (7)0.0460 (8)0.0028 (6)0.0071 (6)−0.0001 (6)
O10.0481 (8)0.0373 (7)0.0668 (9)−0.0048 (6)0.0071 (7)−0.0017 (6)
O20.0476 (7)0.0409 (6)0.0292 (6)0.0123 (5)0.0078 (5)0.0049 (5)
O30.0339 (7)0.0675 (9)0.0444 (7)−0.0035 (6)−0.0003 (6)−0.0090 (6)
O40.0411 (8)0.0710 (9)0.0645 (9)−0.0105 (7)0.0165 (7)0.0170 (7)
S10.0694 (4)0.0521 (3)0.0579 (3)0.0147 (3)−0.0006 (3)0.0201 (2)
Fe10.03822 (15)0.03383 (13)0.03325 (13)0.00572 (10)0.00597 (10)−0.00222 (9)
Geometric parameters (Å, º) top
C1—O11.205 (2)C19—H190.9300
C1—C21.469 (2)C20—C211.380 (3)
C1—C121.582 (2)C20—H200.9300
C2—C31.380 (3)C21—C221.380 (3)
C2—C111.397 (3)C21—H210.9300
C3—C41.397 (3)C22—C231.390 (2)
C3—H30.9300C22—H220.9300
C4—C51.366 (4)C23—O21.3799 (19)
C4—H40.9300C24—O21.4330 (19)
C5—C61.411 (3)C24—C251.498 (2)
C5—H50.9300C24—H240.9800
C6—C71.404 (3)C25—C291.419 (3)
C6—C111.410 (2)C25—C261.424 (3)
C7—C81.357 (4)C25—Fe12.0206 (16)
C7—H70.9300C26—C271.419 (3)
C8—C91.424 (3)C26—Fe12.0263 (19)
C8—H80.9300C26—H260.9800
C9—C101.363 (3)C27—C281.388 (4)
C9—H90.9300C27—Fe12.033 (2)
C10—C111.409 (3)C27—H270.9800
C10—C121.524 (2)C28—C291.414 (3)
C12—N11.474 (2)C28—Fe12.027 (2)
C12—C171.566 (2)C28—H280.9800
C13—N11.437 (2)C29—Fe12.0197 (19)
C13—S11.857 (2)C29—H290.9800
C13—H13A0.9700C30—C341.401 (3)
C13—H13B0.9700C30—C311.410 (3)
C14—C151.544 (2)C30—Fe12.026 (2)
C14—S11.813 (2)C30—H300.9800
C14—H14A0.9700C31—C321.403 (3)
C14—H14B0.9700C31—Fe12.039 (2)
C15—N11.460 (2)C31—H310.9800
C15—C161.530 (2)C32—C331.401 (3)
C15—H150.9800C32—Fe12.042 (2)
C16—N21.508 (2)C32—H320.9800
C16—C171.538 (2)C33—C341.410 (3)
C16—C241.550 (2)C33—Fe12.030 (2)
C17—C181.506 (2)C33—H330.9800
C17—H170.9800C34—Fe12.022 (2)
C18—C231.378 (2)C34—H340.9800
C18—C191.395 (2)N2—O41.2158 (19)
C19—C201.384 (3)N2—O31.2186 (19)
O1—C1—C2128.05 (16)C25—C26—H26126.3
O1—C1—C12124.22 (15)Fe1—C26—H26126.3
C2—C1—C12107.71 (14)C28—C27—C26108.86 (19)
C3—C2—C11120.08 (18)C28—C27—Fe169.77 (12)
C3—C2—C1132.09 (19)C26—C27—Fe169.27 (11)
C11—C2—C1107.83 (15)C28—C27—H27125.6
C2—C3—C4117.6 (2)C26—C27—H27125.6
C2—C3—H3121.2Fe1—C27—H27125.6
C4—C3—H3121.2C27—C28—C29108.34 (19)
C5—C4—C3122.9 (2)C27—C28—Fe170.25 (13)
C5—C4—H4118.6C29—C28—Fe169.27 (11)
C3—C4—H4118.6C27—C28—H28125.8
C4—C5—C6121.1 (2)C29—C28—H28125.8
C4—C5—H5119.4Fe1—C28—H28125.8
C6—C5—H5119.4C28—C29—C25108.0 (2)
C7—C6—C11116.3 (2)C28—C29—Fe169.84 (12)
C7—C6—C5128.2 (2)C25—C29—Fe169.47 (10)
C11—C6—C5115.5 (2)C28—C29—H29126.0
C8—C7—C6120.43 (19)C25—C29—H29126.0
C8—C7—H7119.8Fe1—C29—H29126.0
C6—C7—H7119.8C34—C30—C31108.0 (2)
C7—C8—C9122.6 (2)C34—C30—Fe169.59 (12)
C7—C8—H8118.7C31—C30—Fe170.19 (12)
C9—C8—H8118.7C34—C30—H30126.0
C10—C9—C8118.8 (2)C31—C30—H30126.0
C10—C9—H9120.6Fe1—C30—H30126.0
C8—C9—H9120.6C32—C31—C30108.0 (2)
C9—C10—C11118.39 (16)C32—C31—Fe170.00 (12)
C9—C10—C12132.91 (17)C30—C31—Fe169.22 (11)
C11—C10—C12108.70 (15)C32—C31—H31126.0
C2—C11—C10113.68 (15)C30—C31—H31126.0
C2—C11—C6122.87 (18)Fe1—C31—H31126.0
C10—C11—C6123.45 (19)C33—C32—C31108.0 (2)
N1—C12—C10117.90 (13)C33—C32—Fe169.43 (11)
N1—C12—C17104.47 (12)C31—C32—Fe169.79 (11)
C10—C12—C17113.24 (13)C33—C32—H32126.0
N1—C12—C1107.21 (13)C31—C32—H32126.0
C10—C12—C1102.06 (13)Fe1—C32—H32126.0
C17—C12—C1111.98 (13)C32—C33—C34108.1 (2)
N1—C13—S1107.58 (13)C32—C33—Fe170.32 (12)
N1—C13—H13A110.2C34—C33—Fe169.32 (12)
S1—C13—H13A110.2C32—C33—H33125.9
N1—C13—H13B110.2C34—C33—H33125.9
S1—C13—H13B110.2Fe1—C33—H33125.9
H13A—C13—H13B108.5C30—C34—C33107.9 (2)
C15—C14—S1105.19 (13)C30—C34—Fe169.93 (12)
C15—C14—H14A110.7C33—C34—Fe169.95 (12)
S1—C14—H14A110.7C30—C34—H34126.1
C15—C14—H14B110.7C33—C34—H34126.1
S1—C14—H14B110.7Fe1—C34—H34126.1
H14A—C14—H14B108.8C13—N1—C15110.07 (14)
N1—C15—C16101.46 (12)C13—N1—C12119.29 (14)
N1—C15—C14108.15 (13)C15—N1—C12111.06 (13)
C16—C15—C14117.35 (14)O4—N2—O3124.10 (15)
N1—C15—H15109.8O4—N2—C16118.91 (14)
C16—C15—H15109.8O3—N2—C16116.87 (13)
C14—C15—H15109.8C23—O2—C24116.45 (12)
N2—C16—C15112.49 (13)C14—S1—C1392.80 (9)
N2—C16—C17110.46 (12)C29—Fe1—C2541.12 (8)
C15—C16—C17104.88 (12)C29—Fe1—C34105.54 (9)
N2—C16—C24107.42 (12)C25—Fe1—C34116.39 (8)
C15—C16—C24111.08 (12)C29—Fe1—C30126.18 (8)
C17—C16—C24110.55 (12)C25—Fe1—C30106.99 (8)
C18—C17—C16113.96 (13)C34—Fe1—C3040.48 (10)
C18—C17—C12114.58 (13)C29—Fe1—C2669.01 (9)
C16—C17—C12103.97 (12)C25—Fe1—C2641.21 (7)
C18—C17—H17108.0C34—Fe1—C26151.72 (9)
C16—C17—H17108.0C30—Fe1—C26119.19 (10)
C12—C17—H17108.0C29—Fe1—C2840.89 (8)
C23—C18—C19118.06 (16)C25—Fe1—C2868.99 (8)
C23—C18—C17121.07 (14)C34—Fe1—C28126.31 (11)
C19—C18—C17120.87 (15)C30—Fe1—C28164.13 (11)
C20—C19—C18120.93 (19)C26—Fe1—C2868.58 (10)
C20—C19—H19119.5C29—Fe1—C33116.71 (9)
C18—C19—H19119.5C25—Fe1—C33150.45 (8)
C21—C20—C19119.68 (17)C34—Fe1—C3340.73 (9)
C21—C20—H20120.2C30—Fe1—C3368.12 (10)
C19—C20—H20120.2C26—Fe1—C33166.86 (8)
C20—C21—C22120.62 (18)C28—Fe1—C33107.36 (10)
C20—C21—H21119.7C29—Fe1—C2768.18 (10)
C22—C21—H21119.7C25—Fe1—C2768.80 (7)
C21—C22—C23118.88 (19)C34—Fe1—C27164.63 (11)
C21—C22—H22120.6C30—Fe1—C27154.40 (12)
C23—C22—H22120.6C26—Fe1—C2740.93 (9)
C18—C23—O2122.36 (14)C28—Fe1—C2739.98 (10)
C18—C23—C22121.83 (16)C33—Fe1—C27128.18 (9)
O2—C23—C22115.78 (15)C29—Fe1—C31165.30 (8)
O2—C24—C25107.16 (13)C25—Fe1—C31128.46 (9)
O2—C24—C16110.69 (12)C34—Fe1—C3168.11 (10)
C25—C24—C16114.40 (13)C30—Fe1—C3140.58 (9)
O2—C24—H24108.1C26—Fe1—C31109.88 (10)
C25—C24—H24108.1C28—Fe1—C31153.45 (9)
C16—C24—H24108.1C33—Fe1—C3167.79 (10)
C29—C25—C26107.44 (16)C27—Fe1—C31121.25 (11)
C29—C25—C24126.76 (16)C29—Fe1—C32151.41 (9)
C26—C25—C24125.79 (17)C25—Fe1—C32167.14 (9)
C29—C25—Fe169.41 (10)C34—Fe1—C3268.12 (9)
C26—C25—Fe169.61 (10)C30—Fe1—C3268.01 (9)
C24—C25—Fe1125.15 (11)C26—Fe1—C32129.74 (9)
C27—C26—C25107.3 (2)C28—Fe1—C32119.10 (9)
C27—C26—Fe169.80 (12)C33—Fe1—C3240.25 (9)
C25—C26—Fe169.18 (10)C27—Fe1—C32110.24 (9)
C27—C26—H26126.3C31—Fe1—C3240.22 (9)
O1—C1—C2—C3−3.5 (3)C21—C22—C23—C180.6 (3)
C12—C1—C2—C3177.9 (2)C21—C22—C23—O2−177.60 (17)
O1—C1—C2—C11177.00 (18)N2—C16—C24—O2−65.60 (15)
C12—C1—C2—C11−1.61 (19)C15—C16—C24—O2171.00 (12)
C11—C2—C3—C40.0 (3)C17—C16—C24—O254.99 (17)
C1—C2—C3—C4−179.4 (2)N2—C16—C24—C2555.58 (17)
C2—C3—C4—C5−0.8 (3)C15—C16—C24—C25−67.83 (18)
C3—C4—C5—C61.0 (4)C17—C16—C24—C25176.16 (13)
C4—C5—C6—C7179.8 (2)O2—C24—C25—C2946.3 (2)
C4—C5—C6—C11−0.3 (3)C16—C24—C25—C29−76.8 (2)
C11—C6—C7—C81.1 (3)O2—C24—C25—C26−132.02 (17)
C5—C6—C7—C8−179.0 (2)C16—C24—C25—C26104.88 (19)
C6—C7—C8—C90.6 (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—C111.8 (3)C29—C25—C26—C270.3 (2)
C8—C9—C10—C12−179.70 (19)C24—C25—C26—C27178.93 (16)
C3—C2—C11—C10−178.66 (17)Fe1—C25—C26—C2759.64 (14)
C1—C2—C11—C100.9 (2)C29—C25—C26—Fe1−59.33 (12)
C3—C2—C11—C60.6 (3)C24—C25—C26—Fe1119.29 (16)
C1—C2—C11—C6−179.89 (16)C25—C26—C27—C28−0.6 (2)
C9—C10—C11—C2179.08 (17)Fe1—C26—C27—C2858.67 (15)
C12—C10—C11—C20.3 (2)C25—C26—C27—Fe1−59.25 (13)
C9—C10—C11—C6−0.1 (3)C26—C27—C28—C290.6 (2)
C12—C10—C11—C6−178.96 (16)Fe1—C27—C28—C2958.98 (14)
C7—C6—C11—C2179.51 (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—C2559.17 (12)
C5—C6—C11—C10178.75 (18)C27—C28—C29—Fe1−59.59 (15)
C9—C10—C12—N163.2 (3)C26—C25—C29—C280.1 (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—C17119.36 (15)C26—C25—C29—Fe159.46 (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—C320.0 (2)
O1—C1—C12—N1−52.4 (2)Fe1—C30—C31—C32−59.50 (15)
C2—C1—C12—N1126.23 (14)C34—C30—C31—Fe159.54 (14)
O1—C1—C12—C10−177.00 (17)C30—C31—C32—C33−0.1 (2)
C2—C1—C12—C101.68 (17)Fe1—C31—C32—C33−59.08 (15)
O1—C1—C12—C1761.6 (2)C30—C31—C32—Fe159.01 (15)
C2—C1—C12—C17−119.74 (15)C31—C32—C33—C340.1 (2)
S1—C14—C15—N134.99 (16)Fe1—C32—C33—C34−59.23 (14)
S1—C14—C15—C16148.88 (12)C31—C32—C33—Fe159.30 (15)
N1—C15—C16—N2157.43 (12)C31—C30—C34—C330.0 (2)
C14—C15—C16—N239.87 (19)Fe1—C30—C34—C3359.93 (14)
N1—C15—C16—C1737.33 (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—C24160.32 (14)C32—C33—C34—Fe159.86 (15)
N2—C16—C17—C1885.38 (16)S1—C13—N1—C1531.86 (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—C1292.05 (14)C14—C15—N1—C1290.01 (16)
N1—C12—C17—C18132.57 (13)C10—C12—N1—C1319.8 (2)
C10—C12—C17—C18−97.87 (16)C17—C12—N1—C13146.48 (15)
C1—C12—C17—C1816.87 (18)C1—C12—N1—C13−94.53 (17)
N1—C12—C17—C167.54 (15)C10—C12—N1—C15−109.86 (16)
C10—C12—C17—C16137.10 (14)C17—C12—N1—C1516.86 (16)
C1—C12—C17—C16−108.16 (14)C1—C12—N1—C15135.85 (13)
C16—C17—C18—C238.6 (2)C15—C16—N2—O422.38 (19)
C12—C17—C18—C23−111.04 (17)C17—C16—N2—O4139.20 (15)
C16—C17—C18—C19−172.07 (15)C24—C16—N2—O4−100.16 (16)
C12—C17—C18—C1968.33 (19)C15—C16—N2—O3−161.40 (13)
C23—C18—C19—C200.4 (3)C17—C16—N2—O3−44.58 (18)
C17—C18—C19—C20−178.95 (17)C24—C16—N2—O376.06 (16)
C18—C19—C20—C210.2 (3)C18—C23—O2—C2426.5 (2)
C19—C20—C21—C22−0.5 (3)C22—C23—O2—C24−155.38 (15)
C20—C21—C22—C230.1 (3)C25—C24—O2—C23−177.50 (13)
C19—C18—C23—O2177.22 (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—C22178.54 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13A···O3i0.972.503.417 (3)157
C20—H20···O4ii0.932.593.440 (3)152
C24—H24···O10.982.513.301 (3)138
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x+1/2, −y+1/2, z−1/2.
(II) 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 top
Crystal data top
C31H24N2O5SZ = 2
Mr = 536.58F(000) = 560
Triclinic, P1Dx = 1.416 Mg m−3
a = 11.1123 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.6373 (2) ÅCell parameters from 5157 reflections
c = 12.4095 (3) Åθ = 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) Å30.22 × 0.18 × 0.10 mm
Data collection top
Bruker SMART APEXII area-detector
diffractometer		4192 reflections with I > 2σ(I)
ω and φ scansRint = 0.023
Absorption correction: multi-scan
(SADABS; Bruker, 2008)		θmax = 26.4°, θmin = 2.0°
Tmin = 0.746, Tmax = 0.845h = −13→13
18670 measured reflectionsk = −14→14
5157 independent reflectionsl = −15→15
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H-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 reflectionsΔρmax = 0.25 e Å−3
353 parametersΔρmin = −0.29 e Å−3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.16234 (14)0.21087 (14)1.00050 (14)0.0303 (3)
C20.29371 (14)0.31519 (15)1.06617 (14)0.0334 (3)
C30.35025 (16)0.44717 (16)1.17791 (16)0.0426 (4)
H30.30360.48661.22730.051*
C40.48101 (18)0.52074 (18)1.2151 (2)0.0555 (5)
H40.52040.61081.28950.067*
C50.55205 (18)0.46379 (19)1.1449 (2)0.0596 (5)
H50.63830.51601.17290.071*
C60.49749 (16)0.32733 (18)1.03078 (18)0.0466 (4)
C70.55832 (18)0.2539 (2)0.9491 (2)0.0587 (5)
H70.64560.29560.96910.070*
C80.48953 (18)0.1227 (2)0.8415 (2)0.0567 (5)
H80.53200.07650.78980.068*
C90.35631 (16)0.05349 (18)0.80482 (17)0.0456 (4)
H90.3117−0.03590.72970.055*
C100.29429 (14)0.12055 (15)0.88192 (15)0.0338 (3)
C110.36606 (14)0.25606 (15)0.99389 (15)0.0350 (3)
C120.15158 (13)0.08333 (14)0.86708 (14)0.0296 (3)
C170.04423 (13)0.07120 (14)0.73580 (14)0.0300 (3)
H170.07880.04200.66790.036*
C180.01547 (14)0.20175 (15)0.76059 (14)0.0330 (3)
C190.10115 (16)0.30340 (17)0.76795 (17)0.0422 (4)
H190.17600.28850.75290.051*
C200.07654 (18)0.42587 (18)0.7973 (2)0.0537 (5)
H200.13390.49250.80080.064*
C21−0.03321 (18)0.44951 (18)0.8216 (2)0.0539 (5)
H21−0.04840.53310.84370.065*
C22−0.12025 (16)0.34983 (16)0.81319 (17)0.0464 (4)
H22−0.19410.36590.83000.056*
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)
H24−0.13060.02270.84310.039*
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)
H30−0.4010−0.04380.54100.047*
C29−0.54640 (16)−0.19207 (17)0.50438 (17)0.0453 (4)
H29−0.6151−0.19370.43320.054*
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−0.6753−0.53230.46700.104*
H31B−0.8259−0.53220.42710.104*
H31C−0.7160−0.44190.58060.104*
C27−0.47286 (17)−0.27538 (18)0.65139 (18)0.0481 (4)
H27−0.4906−0.33350.67970.058*
C26−0.34419 (15)−0.18291 (18)0.71723 (16)0.0420 (4)
H26−0.2765−0.17950.79020.050*
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)
H15−0.0812−0.19640.72990.043*
C140.04383 (17)−0.23249 (16)0.63316 (17)0.0456 (4)
H14A0.0794−0.18800.59640.055*
H14B−0.0246−0.31940.55790.055*
C130.18494 (18)−0.11019 (17)0.90177 (18)0.0451 (4)
H13A0.1559−0.14190.95100.054*
H13B0.2769−0.04760.96210.054*
N10.09591 (12)−0.04224 (12)0.85801 (12)0.0338 (3)
N2−0.16219 (13)−0.11755 (14)0.53086 (13)0.0409 (3)
O10.07738 (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)
S10.17845 (6)−0.25726 (5)0.74712 (6)0.06168 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0301 (7)0.0321 (7)0.0293 (7)0.0130 (6)0.0119 (6)0.0175 (6)
C20.0312 (7)0.0345 (8)0.0328 (7)0.0120 (6)0.0114 (6)0.0187 (6)
C30.0398 (8)0.0347 (8)0.0419 (8)0.0123 (7)0.0141 (7)0.0157 (7)
C40.0441 (9)0.0352 (9)0.0585 (11)0.0029 (7)0.0138 (8)0.0135 (8)
C50.0361 (9)0.0491 (11)0.0702 (12)−0.0016 (8)0.0169 (8)0.0235 (10)
C60.0313 (8)0.0496 (10)0.0552 (10)0.0094 (7)0.0171 (7)0.0280 (8)
C70.0335 (9)0.0705 (13)0.0716 (12)0.0135 (9)0.0282 (9)0.0353 (11)
C80.0428 (9)0.0705 (13)0.0626 (11)0.0248 (9)0.0348 (9)0.0309 (10)
C90.0397 (8)0.0479 (10)0.0469 (9)0.0175 (7)0.0242 (7)0.0198 (8)
C100.0295 (7)0.0388 (8)0.0360 (7)0.0137 (6)0.0151 (6)0.0215 (7)
C110.0291 (7)0.0377 (8)0.0383 (8)0.0115 (6)0.0133 (6)0.0219 (7)
C120.0293 (7)0.0296 (7)0.0312 (7)0.0114 (6)0.0147 (6)0.0162 (6)
C170.0293 (7)0.0315 (7)0.0285 (7)0.0087 (6)0.0140 (5)0.0153 (6)
C180.0320 (7)0.0331 (7)0.0294 (7)0.0081 (6)0.0090 (6)0.0175 (6)
C190.0386 (8)0.0416 (9)0.0494 (9)0.0092 (7)0.0171 (7)0.0292 (8)
C200.0474 (10)0.0427 (10)0.0685 (12)0.0070 (8)0.0164 (9)0.0366 (9)
C210.0479 (10)0.0341 (9)0.0647 (11)0.0123 (7)0.0108 (8)0.0266 (8)
C220.0367 (8)0.0380 (9)0.0515 (9)0.0139 (7)0.0124 (7)0.0200 (8)
C230.0308 (7)0.0315 (7)0.0349 (7)0.0068 (6)0.0088 (6)0.0157 (6)
C240.0317 (7)0.0324 (7)0.0315 (7)0.0098 (6)0.0152 (6)0.0151 (6)
C250.0299 (7)0.0331 (7)0.0316 (7)0.0105 (6)0.0142 (6)0.0162 (6)
C300.0368 (8)0.0396 (8)0.0413 (8)0.0091 (7)0.0123 (7)0.0255 (7)
C290.0347 (8)0.0464 (9)0.0422 (9)0.0078 (7)0.0054 (7)0.0245 (8)
C280.0327 (8)0.0390 (8)0.0441 (9)0.0042 (6)0.0141 (7)0.0176 (7)
C310.0636 (12)0.0463 (11)0.0810 (14)−0.0031 (9)0.0374 (11)0.0227 (10)
C270.0418 (9)0.0533 (10)0.0589 (10)0.0097 (8)0.0215 (8)0.0389 (9)
C260.0352 (8)0.0543 (10)0.0431 (8)0.0129 (7)0.0145 (7)0.0334 (8)
C160.0310 (7)0.0304 (7)0.0269 (7)0.0069 (6)0.0132 (6)0.0118 (6)
C150.0376 (8)0.0282 (7)0.0392 (8)0.0090 (6)0.0203 (6)0.0151 (6)
C140.0523 (10)0.0332 (8)0.0487 (9)0.0159 (7)0.0277 (8)0.0163 (7)
C130.0530 (10)0.0438 (9)0.0514 (9)0.0249 (8)0.0262 (8)0.0311 (8)
N10.0363 (6)0.0312 (6)0.0373 (6)0.0129 (5)0.0174 (5)0.0198 (5)
N20.0362 (7)0.0433 (8)0.0306 (6)0.0059 (6)0.0147 (5)0.0126 (6)
O10.0362 (5)0.0429 (6)0.0366 (6)0.0130 (5)0.0201 (5)0.0162 (5)
O20.0356 (6)0.0318 (6)0.0648 (7)0.0117 (5)0.0261 (5)0.0214 (5)
O30.0608 (8)0.0663 (8)0.0370 (6)0.0120 (6)0.0136 (6)0.0296 (6)
O40.0537 (7)0.0416 (7)0.0383 (6)−0.0039 (6)0.0137 (5)0.0034 (5)
O50.0394 (6)0.0582 (8)0.0674 (8)−0.0082 (6)0.0094 (6)0.0297 (7)
S10.0781 (4)0.0513 (3)0.0716 (3)0.0425 (3)0.0426 (3)0.0342 (3)
Geometric parameters (Å, º) top
C1—O11.2085 (17)C22—H220.9300
C1—C21.471 (2)C23—O21.3728 (18)
C1—C121.5783 (19)C24—O21.4291 (18)
C2—C31.373 (2)C24—C251.5090 (19)
C2—C111.402 (2)C24—C161.5612 (19)
C3—C41.405 (2)C24—H240.9800
C3—H30.9300C25—C261.376 (2)
C4—C51.367 (3)C25—C301.394 (2)
C4—H40.9300C30—C291.373 (2)
C5—C61.415 (3)C30—H300.9300
C5—H50.9300C29—C281.383 (2)
C6—C111.404 (2)C29—H290.9300
C6—C71.415 (3)C28—O51.3652 (18)
C7—C81.359 (3)C28—C271.374 (2)
C7—H70.9300C31—O51.413 (2)
C8—C91.414 (2)C31—H31A0.9600
C8—H80.9300C31—H31B0.9600
C9—C101.369 (2)C31—H31C0.9600
C9—H90.9300C27—C261.388 (2)
C10—C111.408 (2)C27—H270.9300
C10—C121.5242 (19)C26—H260.9300
C12—N11.4682 (18)C16—N21.5061 (18)
C12—C171.5714 (19)C16—C151.528 (2)
C17—C181.494 (2)C15—N11.4572 (19)
C17—C161.5331 (19)C15—C141.542 (2)
C17—H170.9800C15—H150.9800
C18—C231.384 (2)C14—S11.8111 (18)
C18—C191.392 (2)C14—H14A0.9700
C19—C201.378 (2)C14—H14B0.9700
C19—H190.9300C13—N11.438 (2)
C20—C211.379 (3)C13—S11.8521 (17)
C20—H200.9300C13—H13A0.9700
C21—C221.376 (2)C13—H13B0.9700
C21—H210.9300N2—O31.2164 (18)
C22—C231.384 (2)N2—O41.2215 (17)
O1—C1—C2127.79 (13)O2—C24—C25105.19 (11)
O1—C1—C12124.36 (12)O2—C24—C16113.86 (11)
C2—C1—C12107.80 (11)C25—C24—C16114.99 (11)
C3—C2—C11120.59 (14)O2—C24—H24107.5
C3—C2—C1132.13 (14)C25—C24—H24107.5
C11—C2—C1107.27 (12)C16—C24—H24107.5
C2—C3—C4117.80 (16)C26—C25—C30117.72 (13)
C2—C3—H3121.1C26—C25—C24121.29 (13)
C4—C3—H3121.1C30—C25—C24120.97 (13)
C5—C4—C3121.91 (16)C29—C30—C25120.97 (14)
C5—C4—H4119.0C29—C30—H30119.5
C3—C4—H4119.0C25—C30—H30119.5
C4—C5—C6121.62 (16)C30—C29—C28120.37 (15)
C4—C5—H5119.2C30—C29—H29119.8
C6—C5—H5119.2C28—C29—H29119.8
C11—C6—C5115.69 (16)O5—C28—C27124.78 (15)
C11—C6—C7116.01 (16)O5—C28—C29115.62 (15)
C5—C6—C7128.30 (16)C27—C28—C29119.60 (14)
C8—C7—C6120.19 (16)O5—C31—H31A109.5
C8—C7—H7119.9O5—C31—H31B109.5
C6—C7—H7119.9H31A—C31—H31B109.5
C7—C8—C9122.90 (16)O5—C31—H31C109.5
C7—C8—H8118.6H31A—C31—H31C109.5
C9—C8—H8118.6H31B—C31—H31C109.5
C10—C9—C8118.72 (16)C28—C27—C26119.50 (15)
C10—C9—H9120.6C28—C27—H27120.2
C8—C9—H9120.6C26—C27—H27120.2
C9—C10—C11118.31 (14)C25—C26—C27121.81 (14)
C9—C10—C12132.99 (14)C25—C26—H26119.1
C11—C10—C12108.51 (12)C27—C26—H26119.1
C2—C11—C6122.37 (14)N2—C16—C15111.92 (12)
C2—C11—C10113.76 (13)N2—C16—C17110.50 (11)
C6—C11—C10123.87 (14)C15—C16—C17103.66 (11)
N1—C12—C10120.51 (12)N2—C16—C24107.57 (11)
N1—C12—C17104.32 (11)C15—C16—C24111.11 (11)
C10—C12—C17110.66 (11)C17—C16—C24112.14 (11)
N1—C12—C1108.87 (11)N1—C15—C16101.78 (11)
C10—C12—C1101.87 (11)N1—C15—C14107.69 (12)
C17—C12—C1110.56 (11)C16—C15—C14116.88 (13)
C18—C17—C16114.61 (12)N1—C15—H15110.0
C18—C17—C12114.00 (11)C16—C15—H15110.0
C16—C17—C12103.47 (11)C14—C15—H15110.0
C18—C17—H17108.1C15—C14—S1104.77 (11)
C16—C17—H17108.1C15—C14—H14A110.8
C12—C17—H17108.1S1—C14—H14A110.8
C23—C18—C19118.15 (14)C15—C14—H14B110.8
C23—C18—C17120.18 (13)S1—C14—H14B110.8
C19—C18—C17121.66 (14)H14A—C14—H14B108.9
C20—C19—C18120.87 (16)N1—C13—S1107.70 (11)
C20—C19—H19119.6N1—C13—H13A110.2
C18—C19—H19119.6S1—C13—H13A110.2
C19—C20—C21119.93 (16)N1—C13—H13B110.2
C19—C20—H20120.0S1—C13—H13B110.2
C21—C20—H20120.0H13A—C13—H13B108.5
C22—C21—C20120.20 (16)C13—N1—C15110.12 (12)
C22—C21—H21119.9C13—N1—C12120.18 (12)
C20—C21—H21119.9C15—N1—C12111.07 (11)
C21—C22—C23119.54 (16)O3—N2—O4124.37 (14)
C21—C22—H22120.2O3—N2—C16117.71 (13)
C23—C22—H22120.2O4—N2—C16117.82 (13)
O2—C23—C18123.07 (13)C23—O2—C24121.41 (11)
O2—C23—C22115.68 (14)C28—O5—C31118.60 (15)
C18—C23—C22121.20 (14)C14—S1—C1392.72 (7)
O1—C1—C2—C3−7.6 (3)O2—C24—C25—C26−138.70 (14)
C12—C1—C2—C3174.87 (16)C16—C24—C25—C2695.21 (17)
O1—C1—C2—C11171.08 (14)O2—C24—C25—C3039.81 (17)
C12—C1—C2—C11−6.50 (15)C16—C24—C25—C30−86.28 (17)
C11—C2—C3—C41.2 (2)C26—C25—C30—C29−0.6 (2)
C1—C2—C3—C4179.63 (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—C60.0 (3)C30—C29—C28—O5−179.01 (16)
C4—C5—C6—C110.9 (3)C30—C29—C28—C271.5 (3)
C4—C5—C6—C7−179.3 (2)O5—C28—C27—C26179.69 (16)
C11—C6—C7—C80.5 (3)C29—C28—C27—C26−0.9 (3)
C5—C6—C7—C8−179.3 (2)C30—C25—C26—C271.2 (2)
C6—C7—C8—C90.5 (3)C24—C25—C26—C27179.76 (15)
C7—C8—C9—C10−1.0 (3)C28—C27—C26—C25−0.5 (3)
C8—C9—C10—C110.5 (2)C18—C17—C16—N282.79 (14)
C8—C9—C10—C12174.67 (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—C101.34 (17)C12—C17—C16—C2487.52 (13)
C5—C6—C11—C2−0.8 (2)O2—C24—C16—N2−79.34 (14)
C7—C6—C11—C2179.40 (16)C25—C24—C16—N242.14 (16)
C5—C6—C11—C10178.78 (16)O2—C24—C16—C15157.84 (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—C1742.35 (16)
C12—C10—C11—C24.61 (17)C25—C24—C16—C17163.83 (12)
C9—C10—C11—C60.6 (2)N2—C16—C15—N1158.74 (11)
C12—C10—C11—C6−174.99 (14)C17—C16—C15—N139.65 (13)
C9—C10—C12—N156.9 (2)C24—C16—C15—N1−80.99 (13)
C11—C10—C12—N1−128.44 (13)N2—C16—C15—C1441.75 (17)
C9—C10—C12—C17−65.0 (2)C17—C16—C15—C14−77.34 (15)
C11—C10—C12—C17109.62 (13)C24—C16—C15—C14162.02 (12)
C9—C10—C12—C1177.43 (17)N1—C15—C14—S137.43 (14)
C11—C10—C12—C1−7.94 (15)C16—C15—C14—S1151.13 (11)
O1—C1—C12—N1−40.63 (18)S1—C13—N1—C1530.38 (15)
C2—C1—C12—N1137.05 (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—C108.73 (14)C14—C15—N1—C13−44.91 (16)
O1—C1—C12—C1773.41 (17)C16—C15—N1—C12−32.75 (14)
C2—C1—C12—C17−108.91 (12)C14—C15—N1—C1290.71 (14)
N1—C12—C17—C18138.20 (12)C10—C12—N1—C1318.04 (19)
C10—C12—C17—C18−90.79 (14)C17—C12—N1—C13143.01 (13)
C1—C12—C17—C1821.31 (16)C1—C12—N1—C13−98.94 (14)
N1—C12—C17—C1613.06 (13)C10—C12—N1—C15−112.52 (14)
C10—C12—C17—C16144.08 (11)C17—C12—N1—C1512.44 (14)
C1—C12—C17—C16−103.82 (12)C1—C12—N1—C15130.49 (12)
C16—C17—C18—C2320.89 (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—O384.76 (15)
C12—C17—C18—C1980.65 (17)C15—C16—N2—O430.56 (18)
C23—C18—C19—C201.9 (2)C17—C16—N2—O4145.53 (13)
C17—C18—C19—C20−176.89 (15)C24—C16—N2—O4−91.76 (15)
C18—C19—C20—C210.8 (3)C18—C23—O2—C2413.6 (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—O2173.50 (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—C31167.94 (17)
C17—C18—C23—C22174.92 (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—C183.1 (2)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C25–C30 and C2–C11 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C17—H17···O3i0.982.473.412 (2)161
C24—H24···O10.982.503.178 (19)126
C8—H8···Cg1ii0.932.823.759 (2)148
C27—H27···Cg2iii0.932.793.720 (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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ISSN: 2056-9890
Volume 72| Part 8| August 2016| Pages 1126-1129
https://doi.org/10.1107/S2056989016011336
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