(3aR,8bR)-3a,8b-Dihy­droxy-1-(4-meth­oxy­phen­yl)-2-methyl­sulfan­yl-3-nitro-1,8b-di­hydro­indeno­[1,2-b]pyrrol-4(3aH)-one

Nagalakshmi, R.A.; Suresh, J.; Jeyachandran, V.; Kumar, R.R.; Lakshman, P.L.N.

doi:10.1107/S1600536813031279

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 12| December 2013| Pages o1849-o1850

doi:10.1107/S1600536813031279

Open

access

(3aR,8bR)-3a,8b-Dihydroxy-1-(4-methoxyphenyl)-2-methylsulfanyl-3-nitro-1,8b-dihydroindeno[1,2-b]pyrrol-4(3aH)-one

R. A. Nagalakshmi,^a J. Suresh,^a V. Jeyachandran,^b R. Ranjith Kumar ^b and P. L. Nilantha Lakshman ^c ^*

^aDepartment of Physics, The Madura College, Madurai 625 011, India, ^bDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, and ^cDepartment of Food Science and Technology, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
^*Correspondence e-mail: plakshmannilantha@ymail.com

(Received 31 October 2013; accepted 14 November 2013; online 30 November 2013)

In the title compound, C₁₉H₁₆N₂O₆S, the pyrrolidine ring adopts a twisted conformation with puckering parameters q₂ = 0.088 (3) Å and Φ₂ = 61.5 (14)°. The cyclopentane ring adopts a twisted conformation with puckering parameters q₂ = 0.099 (2) Å and Φ₂ = 242.8 (14)°. A weak intramolecular O—H⋯O interaction occurs. In the crystal, pairs of C—H⋯O interactions generate dimers with graph-set motif R₂²(24) and they are interconnected by pairs of O—H⋯O hydrogen bonds, which link the molecules into inversion dimers with graph-set motif R₂²(10).

CCDC reference: 972037

Related literature

For the importance of pyrrolidine derivatives, see: Cordell (1981 ); Morais et al. (2009 ); Bello et al. (2010 ); Obniska et al. (2010 ). For related structures, see: Liu et al. (2008 ); Ghorbani (2012 ). For additional conformation analysis, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₉H₁₆N₂O₆S
M_r = 400.40
Monoclinic, P 2₁ /n
a = 13.6601 (7) Å
b = 8.5782 (5) Å
c = 15.2373 (8) Å
β = 97.684 (3)°
V = 1769.46 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 293 K
0.21 × 0.19 × 0.18 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.967, T_max = 0.974
13771 measured reflections
3311 independent reflections
2661 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.155
S = 1.02
3311 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O5	0.82	2.50	3.014 (3)	122
O3—H3⋯O1ⁱ	0.82	2.06	2.821 (2)	155
C11—H11⋯O6ⁱⁱ	0.93	2.60	3.461 (3)	155
Symmetry codes: (i) -x+2, -y, -z+1; (ii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 972037

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813031279/zq2211sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813031279/zq2211Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813031279/zq2211Isup3.cml

checkCIF report

Comment top

Pyrrolidine ring system is a frequently encountered structural motif in many biologically relevant alkaloids (Cordell, 1981). Pyrrolidine derivatives possess anticonvulsant (Obniska et al., 2010), anti-angiogenic (Morais et al., 2009) and antitumor activities (Bello et al., 2010). In view of the high medicinal value of these compounds in conjunction with our research interests, prompted us to synthesize and report the X-ray studies of the title compound (Fig. 1).

In the title compound, C₁₉H₁₆N₂O₆S, the pyrrolidine ring (N1/C1/C2/C3/C4) adopts a twisted conformation with the puckering parameters q₂ = 0.088 (3) Å and Φ₂ = 61.5 (14) °. The cyclopentane ring (C1/C2/C6–C8) adopts a twisted conformation with the puckering parameters q₂ = 0.099 (2) Å and Φ₂ = 242.8 (14) °. The benzene ring of the indane ring is planar with a r.m.s deviation of 0.0113 (1) °. The methoxy benzene ring (C13–C18) is planar with a r.m.s. deviation of 0.0120 Å. The sum of the C—N—C bond angles around N1 atom (352.99 (18)°) is implying a noticeable flattening of the trigonal pyramidal geometry about N1. The conformation of the methylsulfanyl moiety is antiperiplanar, as evidenced from the torsion angles C5—S1—C4—C3 = 165.1 (2) °. The bond length C4—S1 = 1.727 (2) Å is shorter than S1—C5 = 1.804 (3) Å as found in a similar structure (Ghorbani, 2012). The methyl group of the methyl sulfanyl substituent is tilted towards the plane of the benzene ring as indicated by the angle C4—S1—C5 = 106.52 (11) °. Due to the p - π conjugation of atom O6, the bond distance of O6—C16 (1.371 (2) Å) is significantly shorter than the bond distance of O6—C19 (1.427 (3) Å) as found in a similar structure (Liu et al., 2008). The dihedral angle 68.8 (1) ° between the mean planes of the phenyl ring and of the pyrrolidine ring (C1/C3/C4/N1) indicates that the substituent at N1 is in an equatorial position. The shorter bond lengths, C4—N1 (1.352 (3) Å), C3—N2 (1.385 (3) Å) than the normal C—N (1.47 Å) indicate the electron donating effects of nitrogen atoms.

The crystal structure features a weak intramolecular O—H···O interaction and some intermolecular C—H···O and O—H···O interactions. The O3—H3···O1ⁱ (symmetry code: i = -x+2, -y, -z+1) intermolecular interaction connects, inversely related dimers generating a graph set motif R₂²(10) (Cremer & Pople, 1975). The C11—H11···O6 intermolecular interaction connects dimers generating a graph set motif R₂²(24) (Fig 2).

Related literature top

For the importance of pyrrolidine derivatives, see: Cordell (1981); Morais et al. (2009); Bello et al. (2010); Obniska et al. (2010). For related structures, see: Liu et al. (2008); Ghorbani (2012). For additional conformation analysis, see: Cremer & Pople (1975).

Experimental top

A mixture of (E)-4-methoxy-N-(1-(methylthio)-2-nitrovinyl)aniline (1 mmol) with ninhydrin (1 mmol) in presence of glacial AcOH (3–5 drops) was thoroughly ground in a pestle and mortar at room temperature for 2–10 min. The reaction progress was monitored by thin layer chromatography. After completion of the reaction, the reaction mixture was triturated with crushed ice, the resulting solid filtered off and washed with water to afford the pure product. The compound was further recrystallized from ethanol to obtain suitable crystals for X-ray analysis. Melting point 473 K - 475 K. Yield: 95%

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 20% probability displacement ellipsoids and the atom-numbering scheme. H-atoms are omitted for clarity.
	Fig. 2. The partial packing diagram showing O—H···O and C—H···O interactions.

(3aR,8bR)-3a,8b-Dihydroxy-1-(4-methoxyphenyl)-2-methylsulfanyl-3-nitro-1,8b-dihydroindeno[1,2-b]pyrrol-4(3aH)-one top

Crystal data top

C₁₉H₁₆N₂O₆S	F(000) = 832
M_r = 400.40	D_x = 1.503 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2yn	Cell parameters from 2000 reflections
a = 13.6601 (7) Å	θ = 2–31°
b = 8.5782 (5) Å	µ = 0.23 mm⁻¹
c = 15.2373 (8) Å	T = 293 K
β = 97.684 (3)°	Block, yellow
V = 1769.46 (17) Å³	0.21 × 0.19 × 0.18 mm
Z = 4

Data collection top

Bruker Kappa APEXII diffractometer	3311 independent reflections
Radiation source: fine-focus sealed tube	2661 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
Detector resolution: 0 pixels mm^-1	θ_max = 25.5°, θ_min = 1.9°
ω and ϕ scans	h = −16→15
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −10→7
T_min = 0.967, T_max = 0.974	l = −17→18
13771 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.155	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0989P)² + 0.7209P] where P = (F_o² + 2F_c²)/3
3311 reflections	(Δ/σ)_max < 0.001
253 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

C₁₉H₁₆N₂O₆S	V = 1769.46 (17) Å³
M_r = 400.40	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.6601 (7) Å	µ = 0.23 mm⁻¹
b = 8.5782 (5) Å	T = 293 K
c = 15.2373 (8) Å	0.21 × 0.19 × 0.18 mm
β = 97.684 (3)°

Data collection top

Bruker Kappa APEXII diffractometer	3311 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2661 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.974	R_int = 0.047
13771 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.155	H-atom parameters constrained
S = 1.02	Δρ_max = 0.42 e Å⁻³
3311 reflections	Δρ_min = −0.44 e Å⁻³
253 parameters

Special details top

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ (F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F.² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.70509 (13)	0.0236 (3)	0.42776 (14)	0.0363 (5)
C2	0.82032 (13)	0.0315 (3)	0.43000 (14)	0.0375 (5)
C3	0.82888 (14)	0.0735 (3)	0.33568 (15)	0.0387 (5)
C4	0.73865 (14)	0.0682 (2)	0.28246 (14)	0.0361 (5)
C5	0.60238 (18)	0.0213 (4)	0.12776 (17)	0.0575 (7)
H5A	0.5917	0.0297	0.0644	0.086*
H5B	0.5551	0.0849	0.1525	0.086*
H5C	0.5948	−0.0854	0.1446	0.086*
C6	0.85309 (15)	0.1658 (3)	0.49362 (14)	0.0407 (5)
C7	0.76369 (15)	0.2479 (3)	0.51268 (14)	0.0410 (5)
C8	0.67980 (14)	0.1644 (3)	0.48003 (13)	0.0389 (5)
C9	0.58736 (16)	0.2127 (3)	0.49893 (14)	0.0468 (6)
H9	0.5307	0.1555	0.4797	0.056*
C10	0.58276 (19)	0.3479 (3)	0.54700 (16)	0.0557 (7)
H10	0.5218	0.3826	0.5599	0.067*
C11	0.6668 (2)	0.4338 (3)	0.57670 (18)	0.0609 (7)
H11	0.6611	0.5260	0.6077	0.073*
C12	0.75837 (19)	0.3837 (3)	0.56070 (16)	0.0540 (6)
H12	0.8151	0.4395	0.5816	0.065*
C13	0.56455 (13)	0.0879 (2)	0.31000 (13)	0.0337 (5)
C14	0.54498 (14)	0.2415 (3)	0.28747 (14)	0.0393 (5)
H14	0.5967	0.3094	0.2813	0.047*
C15	0.44902 (14)	0.2942 (3)	0.27415 (15)	0.0413 (5)
H15	0.4355	0.3966	0.2565	0.050*
C16	0.37246 (13)	0.1939 (3)	0.28725 (14)	0.0367 (5)
C17	0.39162 (14)	0.0406 (3)	0.30889 (15)	0.0400 (5)
H17	0.3400	−0.0268	0.3164	0.048*
C18	0.48858 (14)	−0.0138 (3)	0.31960 (14)	0.0377 (5)
H18	0.5020	−0.1180	0.3331	0.045*
C19	0.20231 (15)	0.1754 (3)	0.30760 (19)	0.0563 (7)
H19A	0.1421	0.2340	0.2963	0.085*
H19B	0.2181	0.1579	0.3701	0.085*
H19C	0.1942	0.0771	0.2774	0.085*
N1	0.66559 (11)	0.0372 (2)	0.33164 (11)	0.0349 (4)
N2	0.91927 (13)	0.0968 (2)	0.30602 (14)	0.0452 (5)
O1	0.93701 (11)	0.1960 (2)	0.52411 (12)	0.0554 (5)
O2	0.67032 (10)	−0.11114 (19)	0.46335 (10)	0.0443 (4)
H2	0.6844	−0.1868	0.4346	0.066*
O3	0.86160 (10)	−0.11224 (19)	0.45807 (11)	0.0475 (4)
H3	0.9208	−0.1119	0.4537	0.071*
O4	0.92122 (12)	0.1327 (2)	0.22720 (13)	0.0597 (5)
O5	0.99515 (11)	0.0817 (2)	0.35945 (13)	0.0621 (5)
O6	0.28043 (9)	0.2606 (2)	0.27626 (11)	0.0473 (4)
S1	0.72558 (4)	0.08679 (9)	0.16864 (4)	0.0526 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0206 (9)	0.0434 (13)	0.0459 (11)	0.0030 (8)	0.0079 (8)	0.0032 (9)
C2	0.0209 (9)	0.0407 (12)	0.0519 (12)	0.0040 (8)	0.0077 (8)	−0.0005 (9)
C3	0.0242 (9)	0.0430 (13)	0.0514 (12)	0.0010 (8)	0.0143 (8)	−0.0048 (9)
C4	0.0274 (9)	0.0350 (11)	0.0483 (11)	0.0048 (8)	0.0138 (8)	0.0023 (9)
C5	0.0478 (13)	0.0747 (19)	0.0499 (13)	0.0045 (12)	0.0060 (10)	−0.0085 (13)
C6	0.0293 (10)	0.0464 (13)	0.0466 (11)	0.0039 (9)	0.0056 (8)	−0.0001 (10)
C7	0.0343 (10)	0.0467 (13)	0.0424 (11)	0.0065 (9)	0.0067 (8)	0.0003 (9)
C8	0.0295 (10)	0.0468 (13)	0.0416 (10)	0.0076 (8)	0.0095 (8)	0.0019 (9)
C9	0.0335 (10)	0.0617 (16)	0.0482 (12)	0.0097 (10)	0.0158 (9)	0.0032 (11)
C10	0.0508 (14)	0.0675 (18)	0.0533 (13)	0.0196 (12)	0.0235 (11)	−0.0003 (12)
C11	0.0675 (17)	0.0617 (18)	0.0571 (15)	0.0136 (13)	0.0216 (13)	−0.0126 (13)
C12	0.0523 (14)	0.0603 (17)	0.0505 (13)	0.0019 (11)	0.0104 (11)	−0.0109 (12)
C13	0.0189 (9)	0.0404 (12)	0.0426 (11)	0.0019 (7)	0.0074 (7)	0.0010 (8)
C14	0.0219 (9)	0.0413 (13)	0.0568 (12)	−0.0010 (8)	0.0136 (8)	0.0046 (10)
C15	0.0272 (10)	0.0400 (13)	0.0583 (13)	0.0042 (8)	0.0118 (9)	0.0090 (10)
C16	0.0200 (9)	0.0449 (13)	0.0457 (11)	0.0024 (8)	0.0068 (7)	−0.0011 (9)
C17	0.0218 (9)	0.0444 (13)	0.0547 (12)	−0.0044 (8)	0.0086 (8)	0.0008 (10)
C18	0.0273 (9)	0.0364 (12)	0.0504 (12)	0.0003 (8)	0.0085 (8)	0.0018 (9)
C19	0.0245 (10)	0.0686 (17)	0.0778 (17)	0.0003 (10)	0.0140 (10)	0.0083 (14)
N1	0.0186 (7)	0.0440 (11)	0.0436 (9)	0.0031 (6)	0.0094 (6)	0.0022 (8)
N2	0.0292 (9)	0.0450 (12)	0.0653 (13)	−0.0016 (7)	0.0203 (8)	−0.0069 (9)
O1	0.0299 (8)	0.0645 (12)	0.0697 (11)	0.0010 (7)	−0.0008 (7)	−0.0141 (9)
O2	0.0334 (8)	0.0465 (10)	0.0547 (9)	0.0002 (6)	0.0126 (6)	0.0093 (7)
O3	0.0247 (7)	0.0448 (10)	0.0719 (11)	0.0070 (6)	0.0022 (7)	0.0016 (8)
O4	0.0439 (9)	0.0645 (12)	0.0767 (12)	−0.0021 (8)	0.0300 (8)	0.0084 (10)
O5	0.0217 (8)	0.0881 (14)	0.0779 (12)	−0.0032 (7)	0.0118 (8)	−0.0144 (10)
O6	0.0194 (6)	0.0518 (10)	0.0723 (10)	0.0048 (6)	0.0117 (6)	0.0072 (8)
S1	0.0402 (3)	0.0725 (5)	0.0474 (4)	0.0029 (3)	0.0146 (3)	0.0101 (3)

Geometric parameters (Å, º) top

C1—O2	1.387 (3)	C11—C12	1.375 (4)
C1—N1	1.496 (3)	C11—H11	0.9300
C1—C8	1.512 (3)	C12—H12	0.9300
C1—C2	1.571 (2)	C13—C14	1.378 (3)
C2—O3	1.399 (3)	C13—C18	1.379 (3)
C2—C3	1.501 (3)	C13—N1	1.443 (2)
C2—C6	1.533 (3)	C14—C15	1.376 (3)
C3—C4	1.383 (3)	C14—H14	0.9300
C3—N2	1.385 (3)	C15—C16	1.389 (3)
C4—N1	1.352 (3)	C15—H15	0.9300
C4—S1	1.727 (2)	C16—O6	1.371 (2)
C5—S1	1.804 (3)	C16—C17	1.372 (3)
C5—H5A	0.9600	C17—C18	1.393 (3)
C5—H5B	0.9600	C17—H17	0.9300
C5—H5C	0.9600	C18—H18	0.9300
C6—O1	1.206 (3)	C19—O6	1.427 (3)
C6—C7	1.472 (3)	C19—H19A	0.9600
C7—C12	1.383 (3)	C19—H19B	0.9600
C7—C8	1.386 (3)	C19—H19C	0.9600
C8—C9	1.395 (3)	N2—O5	1.236 (3)
C9—C10	1.378 (4)	N2—O4	1.244 (3)
C9—H9	0.9300	O2—H2	0.8200
C10—C11	1.388 (4)	O3—H3	0.8200
C10—H10	0.9300

O2—C1—N1	110.51 (17)	C12—C11—H11	119.7
O2—C1—C8	110.19 (16)	C10—C11—H11	119.7
N1—C1—C8	112.04 (17)	C11—C12—C7	118.1 (2)
O2—C1—C2	114.95 (16)	C11—C12—H12	121.0
N1—C1—C2	104.30 (15)	C7—C12—H12	121.0
C8—C1—C2	104.65 (16)	C14—C13—C18	120.52 (18)
O3—C2—C3	115.10 (17)	C14—C13—N1	119.52 (17)
O3—C2—C6	113.41 (17)	C18—C13—N1	119.71 (19)
C3—C2—C6	111.82 (18)	C15—C14—C13	120.01 (19)
O3—C2—C1	109.29 (17)	C15—C14—H14	120.0
C3—C2—C1	101.28 (15)	C13—C14—H14	120.0
C6—C2—C1	104.66 (16)	C14—C15—C16	119.7 (2)
C4—C3—N2	125.2 (2)	C14—C15—H15	120.1
C4—C3—C2	112.11 (17)	C16—C15—H15	120.1
N2—C3—C2	122.27 (18)	O6—C16—C17	124.89 (18)
N1—C4—C3	110.34 (18)	O6—C16—C15	114.77 (19)
N1—C4—S1	126.15 (16)	C17—C16—C15	120.34 (18)
C3—C4—S1	123.39 (15)	C16—C17—C18	119.81 (19)
S1—C5—H5A	109.5	C16—C17—H17	120.1
S1—C5—H5B	109.5	C18—C17—H17	120.1
H5A—C5—H5B	109.5	C13—C18—C17	119.5 (2)
S1—C5—H5C	109.5	C13—C18—H18	120.2
H5A—C5—H5C	109.5	C17—C18—H18	120.2
H5B—C5—H5C	109.5	O6—C19—H19A	109.5
O1—C6—C7	126.3 (2)	O6—C19—H19B	109.5
O1—C6—C2	125.94 (19)	H19A—C19—H19B	109.5
C7—C6—C2	107.72 (17)	O6—C19—H19C	109.5
C12—C7—C8	121.7 (2)	H19A—C19—H19C	109.5
C12—C7—C6	127.7 (2)	H19B—C19—H19C	109.5
C8—C7—C6	110.5 (2)	C4—N1—C13	124.66 (17)
C7—C8—C9	120.0 (2)	C4—N1—C1	111.19 (15)
C7—C8—C1	111.45 (17)	C13—N1—C1	117.14 (15)
C9—C8—C1	128.5 (2)	O5—N2—O4	122.52 (18)
C10—C9—C8	117.8 (2)	O5—N2—C3	118.4 (2)
C10—C9—H9	121.1	O4—N2—C3	119.08 (19)
C8—C9—H9	121.1	C1—O2—H2	109.5
C9—C10—C11	121.7 (2)	C2—O3—H3	109.5
C9—C10—H10	119.1	C16—O6—C19	117.35 (18)
C11—C10—H10	119.1	C4—S1—C5	106.52 (11)
C12—C11—C10	120.6 (3)

O2—C1—C2—O3	7.7 (2)	C7—C8—C9—C10	2.8 (3)
N1—C1—C2—O3	−113.49 (18)	C1—C8—C9—C10	−178.9 (2)
C8—C1—C2—O3	128.67 (18)	C8—C9—C10—C11	−0.5 (4)
O2—C1—C2—C3	129.54 (19)	C9—C10—C11—C12	−1.6 (4)
N1—C1—C2—C3	8.4 (2)	C10—C11—C12—C7	1.4 (4)
C8—C1—C2—C3	−109.45 (18)	C8—C7—C12—C11	0.9 (4)
O2—C1—C2—C6	−114.1 (2)	C6—C7—C12—C11	−174.7 (2)
N1—C1—C2—C6	124.73 (18)	C18—C13—C14—C15	−0.2 (3)
C8—C1—C2—C6	6.9 (2)	N1—C13—C14—C15	−174.4 (2)
O3—C2—C3—C4	109.7 (2)	C13—C14—C15—C16	2.8 (3)
C6—C2—C3—C4	−119.03 (19)	C14—C15—C16—O6	177.0 (2)
C1—C2—C3—C4	−8.1 (2)	C14—C15—C16—C17	−3.4 (3)
O3—C2—C3—N2	−63.6 (3)	O6—C16—C17—C18	−179.1 (2)
C6—C2—C3—N2	67.7 (3)	C15—C16—C17—C18	1.4 (3)
C1—C2—C3—N2	178.6 (2)	C14—C13—C18—C17	−1.9 (3)
N2—C3—C4—N1	177.5 (2)	N1—C13—C18—C17	172.37 (19)
C2—C3—C4—N1	4.4 (3)	C16—C17—C18—C13	1.3 (3)
N2—C3—C4—S1	1.3 (3)	C3—C4—N1—C13	151.4 (2)
C2—C3—C4—S1	−171.80 (15)	S1—C4—N1—C13	−32.5 (3)
O3—C2—C6—O1	49.2 (3)	C3—C4—N1—C1	1.8 (2)
C3—C2—C6—O1	−82.9 (3)	S1—C4—N1—C1	177.84 (15)
C1—C2—C6—O1	168.3 (2)	C14—C13—N1—C4	−48.6 (3)
O3—C2—C6—C7	−129.12 (18)	C18—C13—N1—C4	137.1 (2)
C3—C2—C6—C7	98.72 (19)	C14—C13—N1—C1	99.4 (2)
C1—C2—C6—C7	−10.1 (2)	C18—C13—N1—C1	−74.9 (3)
O1—C6—C7—C12	7.6 (4)	O2—C1—N1—C4	−130.78 (17)
C2—C6—C7—C12	−174.1 (2)	C8—C1—N1—C4	105.92 (19)
O1—C6—C7—C8	−168.5 (2)	C2—C1—N1—C4	−6.7 (2)
C2—C6—C7—C8	9.9 (3)	O2—C1—N1—C13	77.1 (2)
C12—C7—C8—C9	−3.1 (3)	C8—C1—N1—C13	−46.2 (2)
C6—C7—C8—C9	173.2 (2)	C2—C1—N1—C13	−158.86 (17)
C12—C7—C8—C1	178.3 (2)	C4—C3—N2—O5	−172.1 (2)
C6—C7—C8—C1	−5.3 (3)	C2—C3—N2—O5	0.3 (3)
O2—C1—C8—C7	122.85 (19)	C4—C3—N2—O4	8.2 (3)
N1—C1—C8—C7	−113.67 (19)	C2—C3—N2—O4	−179.4 (2)
C2—C1—C8—C7	−1.3 (2)	C17—C16—O6—C19	14.1 (3)
O2—C1—C8—C9	−55.6 (3)	C15—C16—O6—C19	−166.3 (2)
N1—C1—C8—C9	67.9 (3)	N1—C4—S1—C5	−10.5 (2)
C2—C1—C8—C9	−179.7 (2)	C3—C4—S1—C5	165.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O5	0.82	2.50	3.014 (3)	122
O3—H3···O1ⁱ	0.82	2.06	2.821 (2)	155
C11—H11···O6ⁱⁱ	0.93	2.60	3.461 (3)	155

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O5	0.82	2.50	3.014 (3)	122.0
O3—H3···O1ⁱ	0.82	2.06	2.821 (2)	154.8
C11—H11···O6ⁱⁱ	0.93	2.60	3.461 (3)	155.1

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+1, −y+1, −z+1.

Acknowledgements

JS and RAN thank the management of the Madura College for their encouragement and support. RRK thanks the DST, New Delhi, for funds under the fast-track scheme (No. SR/FT/CS-073/2009)

References

Bello, C., Cea, M., Dal Bello, G., Garuti, A., Rocco, I., Cirmena, G., Moran, E., Nahimana, A., Duchosal, M. A., Fruscione, F., Pronzato, P., Grossi, F., Patrone, F., Ballestrero, A., Dupuis, M., Sordat, B., Nencioni, A. & Vogel, P. (2010). Bioorg. Med. Chem. 18, 3320–3334. Web of Science CrossRef CAS PubMed Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin,USA. Google Scholar
Cordell, G. A. (1981). In Introduction to Alkaloids: A Biogenetic Approach. New York: Wiley International. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Ghorbani, M. H. (2012). Acta Cryst. E68, o2605. CSD CrossRef IUCr Journals Google Scholar
Liu, P., Liu, Z., Wang, X.-W. & Wang, W. (2008). Acta Cryst. E64, o1406. Web of Science CSD CrossRef IUCr Journals Google Scholar
Morais, C., Gobe, G., Johnson, D. W. & Healy, H. (2009). Angiogenesis, 12, 365–379. Web of Science CrossRef PubMed CAS Google Scholar
Obniska, J., Kopytko, M., Zagórska, A., Chlebek, I. & Kaminski, K. (2010). Arch. Pharm. (Weinheim), 343, 333–341. Web of Science CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 12| December 2013| Pages o1849-o1850

doi:10.1107/S1600536813031279

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(3aR,8bR)-3a,8b-Dihy­dr­oxy-1-(4-meth­­oxy­phen­yl)-2-methyl­sulfan­yl-3-nitro-1,8b-di­hydro­indeno­[1,2-b]pyrrol-4(3aH)-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(3aR,8bR)-3a,8b-Dihydroxy-1-(4-methoxyphenyl)-2-methylsulfanyl-3-nitro-1,8b-dihydroindeno[1,2-b]pyrrol-4(3aH)-one