(3aR,8bR)-3a,8b-Dihy­droxy-2-methyl­sulfanyl-3-nitro-1-phenyl-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/S1600536813029577

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 12| December 2013| Pages o1770-o1771

doi:10.1107/S1600536813029577

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(3aR,8bR)-3a,8b-Dihydroxy-2-methylsulfanyl-3-nitro-1-phenyl-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 22 October 2013; accepted 27 October 2013; online 13 November 2013)

In the title compound, C₁₈H₁₄N₂O₅, the pyrrolidine ring adopts a shallow envelope conformation, with the C atom bearing the OH group (and remote from the N atom) displaced by 0.257 (2) Å from the other atoms. The cyclopentane ring has a twisted conformation about the C—C bond bearing one =O and one —OH grouping. The dihedral angle between the five-membered rings (all atoms) is 65.54 (9)° and the OH groups lie to the same side of the ring-junction. The molecular structure features a weak intramolecular O—H⋯O bond and a possible C—H⋯π interaction. In the crystal, the molecules are linked into [010] chains by O—H⋯O hydrogen bonds. Weak C—H⋯O bonds connect the chains into (100) sheets.

CCDC reference: 968756

Related literature

For background to pyrrolidine derivatives, see: Grigg (1995 ); Kravchenko et al. (2005 ). For ring conformation analysis, see: Cremer & Pople (1975 ). For a related structure, see: Ghorbani (2012 ).

Experimental

Crystal data

C₁₈H₁₄N₂O₅S
M_r = 370.37
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.6625 (3) Å
b = 10.8994 (2) Å
c = 15.8154 (4) Å
V = 1665.61 (7) 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
9249 measured reflections
4140 independent reflections
3800 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.092
S = 1.00
4140 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.19 e Å⁻³
Absolute structure: Flack (1983 )
Absolute structure parameter: 0.00 (6)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C13–C18 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O5	0.82	2.34	2.895 (2)	126
O2—H2⋯O5ⁱ	0.82	2.00	2.8155 (18)	171
C11—H11⋯O4ⁱⁱ	0.93	2.51	3.423 (3)	166
C9—H9⋯Cg1	0.93	2.89	3.545 (2)	129
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y-{\script{1\over 2}}, -z]$ ; (ii) $[-x-{\script{1\over 2}}, -y, z+{\script{1\over 2}}]$ .

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: 968756

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813029577/hb7154sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813029577/hb7154Isup2.hkl

checkCIF report

Comment top

Pyrrolidine-containing compounds are of significant importance because of their biological activities and widespread employment in catalysis (Grigg, 1995; Kravchenko et al., 2005). As part of our own studies in this area, we have undertaken the crystal structure determination of the title compound, a pyrrolidine derivative,and the results are presented here.

In the title compound (Fig 1) C₁₈H₁₄N₂O₅, the central pyrrolidine ring is enveloped on C2 with the puckering parameters q₂ = 0.1576 (16) Å and ϕ₂ = 243.9 (6) ° (Cremer & Pople, 1975). The cyclopentane ring has a twisted conformation with the puckering parameters q₂ = 0.1540 (18) Å and ϕ₂ = 45.5 (7) °. The benzene ring of the indane ring is in planar with r.m.s. deviation 0.007 (1) Å. The benzene ring attached to the pyrrole ring is also planar with r.m.s. deviation 0.0096 Å. The aryl ring makes the dihedral angle of 57.40 (1) ° with the mean plane of the pyrrolidine ring. The sum of the C—N—C angles around N1 (359.89 (1)°) atom is implying a noticeable flattening of the trigonal pyramidal geometry about N1. The conformation of the methylsulfanyl moiety is in anticlinical conformation as evidenced from the torsion angle C5-S1-C4-C3 = -145.2 ° . The nitro group is well ordered and makes a dihedral angle of 20.25 (17) ° with the mean plane of pyrrolidine ring. The twist of the methyl sulfanyl ring attached with the pyrrolidine ring is indicated by the torsion angle C5-S1-C4-N1 = 28.5 °. The bond length C4-S1 = 1.727 (2) Å is shorter than S1-C5 = 1.804 (3) Å as found in 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 conjugation ,the bond length C1-O2 = 1.380 (4)Å is shorter than the bond length C2-O3 = 1.409 (2) Å. The methoxy groups substituted at the phenyl rings are twisted, as it can be seen from the torsion angles C19-O6-C16-C17 = 14.1 (3) °.

The structure features a weak intra-molecular O—H···O interaction. An inter- molecular O2—H2···O5 inteaction forms a zig-zag chain along b axis and they are further connected by C11—H11···O4 inter-molecular interaction, forming a zig-zag chain along c axis. A weak C—H···Cg1 interaction is also observed, as in Table 1 (Cg1 is the centroid of the benzene ring C13-C18).

Related literature top

For background to pyrrolidine derivatives, see: Grigg (1995); Kravchenko et al. (2005). For ring conformation analysis, see: Cremer & Pople (1975). For a related structure, see: Ghorbani (2012).

Experimental top

A mixture of (E)-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 mins. Thereaction 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 colourless blocks. Melting point : 451K - 453K. Yield : 94%.

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 (I), showing 20% probability displacement ellipsoids. H-atoms are omitted for clarity.
	Fig. 2. The partial packing diagram showing 0—H···O and C—H···O interactions.

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

Crystal data top

C₁₈H₁₄N₂O₅S	F(000) = 768
M_r = 370.37	D_x = 1.477 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2000 reflections
a = 9.6625 (3) Å	θ = 2–31°
b = 10.8994 (2) Å	µ = 0.23 mm⁻¹
c = 15.8154 (4) Å	T = 293 K
V = 1665.61 (7) Å³	Block, colourless
Z = 4	0.21 × 0.19 × 0.18 mm

Data collection top

Bruker Kappa APEXII diffractometer	4140 independent reflections
Radiation source: fine-focus sealed tube	3800 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
Detector resolution: 0 pixels mm^-1	θ_max = 28.3°, θ_min = 2.3°
ω and ϕ scans	h = −12→12
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→14
T_min = 0.967, T_max = 0.974	l = −18→21
9249 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.092	w = 1/[σ²(F_o²) + (0.0557P)² + 0.2428P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
4140 reflections	Δρ_max = 0.23 e Å⁻³
236 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 000 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (6)

Crystal data top

C₁₈H₁₄N₂O₅S	V = 1665.61 (7) Å³
M_r = 370.37	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.6625 (3) Å	µ = 0.23 mm⁻¹
b = 10.8994 (2) Å	T = 293 K
c = 15.8154 (4) Å	0.21 × 0.19 × 0.18 mm

Data collection top

Bruker Kappa APEXII diffractometer	4140 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3800 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.974	R_int = 0.018
9249 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.092	Δρ_max = 0.23 e Å⁻³
S = 1.00	Δρ_min = −0.19 e Å⁻³
4140 reflections	Absolute structure: Flack (1983), 000 Friedel pairs
236 parameters	Absolute structure parameter: 0.00 (6)
0 restraints

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	0.14622 (15)	−0.06791 (13)	0.10358 (9)	0.0281 (3)
C2	0.07556 (17)	−0.17588 (14)	0.05420 (10)	0.0322 (3)
C3	0.07626 (16)	−0.12630 (14)	−0.03423 (9)	0.0315 (3)
C4	0.16436 (15)	−0.02676 (14)	−0.04222 (9)	0.0287 (3)
C5	0.3928 (2)	0.0803 (2)	−0.11431 (14)	0.0551 (5)
H5A	0.4342	0.1155	−0.1639	0.083*
H5B	0.4461	0.0106	−0.0964	0.083*
H5C	0.3910	0.1403	−0.0699	0.083*
C6	−0.07130 (19)	−0.18225 (19)	0.09064 (12)	0.0447 (4)
C7	−0.09638 (18)	−0.06680 (17)	0.13669 (12)	0.0426 (4)
C8	0.02672 (16)	−0.00269 (14)	0.14699 (9)	0.0326 (3)
C9	0.0300 (2)	0.10338 (17)	0.19568 (11)	0.0438 (4)
H9	0.1121	0.1461	0.2044	0.053*
C10	−0.0939 (3)	0.1434 (2)	0.23091 (13)	0.0583 (6)
H10	−0.0941	0.2146	0.2633	0.070*
C11	−0.2169 (3)	0.0807 (2)	0.21922 (15)	0.0663 (6)
H11	−0.2982	0.1110	0.2428	0.080*
C12	−0.2199 (2)	−0.0259 (2)	0.17303 (15)	0.0612 (5)
H12	−0.3018	−0.0697	0.1661	0.073*
C13	0.25948 (16)	0.12942 (13)	0.05639 (10)	0.0318 (3)
C14	0.3684 (2)	0.14182 (18)	0.11299 (11)	0.0446 (4)
H14	0.4143	0.0729	0.1335	0.054*
C15	0.4078 (2)	0.2584 (2)	0.13854 (14)	0.0559 (5)
H15	0.4781	0.2674	0.1782	0.067*
C16	0.3443 (3)	0.36057 (19)	0.10607 (15)	0.0605 (6)
H16	0.3729	0.4383	0.1229	0.073*
C17	0.2376 (2)	0.34801 (17)	0.04819 (16)	0.0566 (5)
H17	0.1954	0.4173	0.0255	0.068*
C18	0.1936 (2)	0.23165 (15)	0.02401 (12)	0.0430 (4)
H18	0.1203	0.2227	−0.0136	0.052*
N1	0.21036 (13)	0.00884 (11)	0.03503 (7)	0.0280 (2)
N2	0.02304 (15)	−0.19222 (14)	−0.10135 (10)	0.0405 (3)
O1	−0.14751 (19)	−0.26911 (18)	0.08517 (13)	0.0783 (6)
O2	0.24185 (12)	−0.10349 (10)	0.16359 (7)	0.0339 (2)
H2	0.3065	−0.1386	0.1404	0.051*
O3	0.14813 (16)	−0.28697 (11)	0.06474 (9)	0.0464 (3)
H3	0.1156	−0.3392	0.0331	0.070*
O4	0.01453 (17)	−0.14460 (16)	−0.17197 (9)	0.0568 (4)
O5	−0.01833 (16)	−0.30050 (13)	−0.08714 (10)	0.0559 (4)
S1	0.21819 (5)	0.03237 (4)	−0.13829 (2)	0.04134 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0308 (7)	0.0277 (6)	0.0257 (6)	−0.0027 (5)	0.0015 (5)	0.0009 (5)
C2	0.0339 (7)	0.0293 (7)	0.0336 (7)	−0.0048 (6)	−0.0008 (6)	−0.0018 (6)
C3	0.0317 (7)	0.0334 (7)	0.0295 (7)	0.0016 (6)	−0.0019 (6)	−0.0056 (6)
C4	0.0297 (6)	0.0302 (7)	0.0262 (6)	0.0051 (6)	0.0003 (5)	−0.0009 (5)
C5	0.0551 (11)	0.0604 (12)	0.0497 (10)	−0.0134 (10)	0.0204 (9)	−0.0003 (9)
C6	0.0372 (8)	0.0548 (11)	0.0421 (9)	−0.0125 (8)	0.0044 (7)	−0.0029 (8)
C7	0.0355 (8)	0.0529 (10)	0.0395 (8)	−0.0020 (7)	0.0064 (7)	0.0023 (8)
C8	0.0355 (7)	0.0361 (7)	0.0262 (6)	0.0027 (6)	0.0047 (6)	0.0031 (6)
C9	0.0557 (11)	0.0398 (8)	0.0359 (8)	0.0028 (8)	0.0116 (8)	−0.0025 (7)
C10	0.0778 (16)	0.0532 (11)	0.0441 (10)	0.0179 (11)	0.0222 (10)	−0.0019 (9)
C11	0.0537 (13)	0.0828 (15)	0.0625 (13)	0.0234 (12)	0.0275 (11)	0.0038 (12)
C12	0.0374 (9)	0.0844 (15)	0.0616 (12)	0.0002 (11)	0.0152 (9)	0.0022 (11)
C13	0.0357 (8)	0.0300 (7)	0.0297 (7)	−0.0073 (6)	0.0046 (6)	−0.0022 (5)
C14	0.0445 (9)	0.0487 (10)	0.0408 (9)	−0.0166 (8)	−0.0042 (7)	0.0046 (7)
C15	0.0618 (12)	0.0596 (11)	0.0462 (10)	−0.0313 (10)	−0.0019 (10)	−0.0048 (10)
C16	0.0737 (14)	0.0452 (11)	0.0626 (12)	−0.0282 (10)	0.0175 (11)	−0.0168 (9)
C17	0.0615 (13)	0.0334 (8)	0.0749 (14)	−0.0024 (9)	0.0114 (11)	−0.0033 (9)
C18	0.0438 (10)	0.0353 (8)	0.0498 (10)	0.0015 (7)	0.0015 (8)	−0.0031 (7)
N1	0.0304 (6)	0.0273 (5)	0.0262 (5)	−0.0031 (5)	0.0021 (5)	−0.0003 (4)
N2	0.0346 (7)	0.0460 (8)	0.0409 (8)	0.0039 (6)	−0.0072 (6)	−0.0161 (6)
O1	0.0633 (10)	0.0836 (12)	0.0880 (12)	−0.0434 (10)	0.0184 (9)	−0.0231 (10)
O2	0.0361 (6)	0.0368 (5)	0.0288 (5)	0.0014 (5)	−0.0028 (4)	0.0014 (4)
O3	0.0615 (8)	0.0269 (5)	0.0507 (7)	0.0006 (5)	−0.0068 (6)	−0.0009 (5)
O4	0.0583 (9)	0.0755 (10)	0.0365 (7)	0.0049 (8)	−0.0143 (6)	−0.0108 (6)
O5	0.0563 (8)	0.0461 (7)	0.0652 (9)	−0.0123 (6)	−0.0069 (7)	−0.0198 (7)
S1	0.0506 (2)	0.0458 (2)	0.02760 (17)	0.00591 (19)	0.00479 (17)	0.00507 (16)

Geometric parameters (Å, º) top

C1—O2	1.3802 (18)	C10—C11	1.383 (4)
C1—N1	1.5030 (18)	C10—H10	0.9300
C1—C8	1.520 (2)	C11—C12	1.373 (4)
C1—C2	1.569 (2)	C11—H11	0.9300
C2—O3	1.409 (2)	C12—H12	0.9300
C2—C3	1.499 (2)	C13—C18	1.382 (2)
C2—C6	1.533 (2)	C13—C14	1.388 (2)
C3—N2	1.3811 (19)	C13—N1	1.4377 (18)
C3—C4	1.385 (2)	C14—C15	1.387 (3)
C4—N1	1.3567 (18)	C14—H14	0.9300
C4—S1	1.7304 (15)	C15—C16	1.371 (3)
C5—S1	1.807 (2)	C15—H15	0.9300
C5—H5A	0.9600	C16—C17	1.386 (4)
C5—H5B	0.9600	C16—H16	0.9300
C5—H5C	0.9600	C17—C18	1.391 (3)
C6—O1	1.202 (2)	C17—H17	0.9300
C6—C7	1.474 (3)	C18—H18	0.9300
C7—C8	1.389 (2)	N2—O4	1.234 (2)
C7—C12	1.398 (3)	N2—O5	1.266 (2)
C8—C9	1.389 (2)	O2—H2	0.8200
C9—C10	1.391 (3)	O3—H3	0.8200
C9—H9	0.9300

O2—C1—N1	112.11 (12)	C11—C10—C9	122.07 (19)
O2—C1—C8	109.23 (12)	C11—C10—H10	119.0
N1—C1—C8	112.26 (11)	C9—C10—H10	119.0
O2—C1—C2	115.02 (12)	C12—C11—C10	120.5 (2)
N1—C1—C2	103.76 (11)	C12—C11—H11	119.7
C8—C1—C2	104.18 (12)	C10—C11—H11	119.7
O3—C2—C3	114.69 (13)	C11—C12—C7	118.1 (2)
O3—C2—C6	112.16 (14)	C11—C12—H12	121.0
C3—C2—C6	111.79 (14)	C7—C12—H12	121.0
O3—C2—C1	111.66 (13)	C18—C13—C14	120.66 (15)
C3—C2—C1	101.07 (12)	C18—C13—N1	119.86 (15)
C6—C2—C1	104.46 (13)	C14—C13—N1	119.39 (15)
N2—C3—C4	124.50 (14)	C15—C14—C13	119.01 (19)
N2—C3—C2	121.85 (14)	C15—C14—H14	120.5
C4—C3—C2	111.73 (13)	C13—C14—H14	120.5
N1—C4—C3	110.08 (13)	C16—C15—C14	120.83 (19)
N1—C4—S1	125.85 (11)	C16—C15—H15	119.6
C3—C4—S1	123.82 (11)	C14—C15—H15	119.6
S1—C5—H5A	109.5	C15—C16—C17	120.00 (17)
S1—C5—H5B	109.5	C15—C16—H16	120.0
H5A—C5—H5B	109.5	C17—C16—H16	120.0
S1—C5—H5C	109.5	C16—C17—C18	120.0 (2)
H5A—C5—H5C	109.5	C16—C17—H17	120.0
H5B—C5—H5C	109.5	C18—C17—H17	120.0
O1—C6—C7	127.37 (19)	C13—C18—C17	119.48 (18)
O1—C6—C2	125.13 (19)	C13—C18—H18	120.3
C7—C6—C2	107.41 (14)	C17—C18—H18	120.3
C8—C7—C12	121.52 (18)	C4—N1—C13	125.54 (12)
C8—C7—C6	110.28 (15)	C4—N1—C1	110.81 (11)
C12—C7—C6	128.00 (18)	C13—N1—C1	118.38 (11)
C7—C8—C9	120.20 (16)	O4—N2—O5	122.11 (15)
C7—C8—C1	111.24 (14)	O4—N2—C3	120.10 (15)
C9—C8—C1	128.48 (15)	O5—N2—C3	117.78 (16)
C8—C9—C10	117.6 (2)	C1—O2—H2	109.5
C8—C9—H9	121.2	C2—O3—H3	109.5
C10—C9—H9	121.2	C4—S1—C5	101.78 (8)

O2—C1—C2—O3	−15.37 (18)	N1—C1—C8—C9	−64.8 (2)
N1—C1—C2—O3	107.44 (14)	C2—C1—C8—C9	−176.43 (15)
C8—C1—C2—O3	−134.90 (13)	C7—C8—C9—C10	−1.7 (3)
O2—C1—C2—C3	−137.77 (13)	C1—C8—C9—C10	−178.21 (16)
N1—C1—C2—C3	−14.95 (14)	C8—C9—C10—C11	0.5 (3)
C8—C1—C2—C3	102.70 (13)	C9—C10—C11—C12	1.2 (4)
O2—C1—C2—C6	106.06 (15)	C10—C11—C12—C7	−1.7 (4)
N1—C1—C2—C6	−131.12 (13)	C8—C7—C12—C11	0.4 (3)
C8—C1—C2—C6	−13.47 (16)	C6—C7—C12—C11	174.7 (2)
O3—C2—C3—N2	59.5 (2)	C18—C13—C14—C15	1.8 (3)
C6—C2—C3—N2	−69.58 (19)	N1—C13—C14—C15	−174.80 (16)
C1—C2—C3—N2	179.80 (14)	C13—C14—C15—C16	−2.6 (3)
O3—C2—C3—C4	−105.35 (15)	C14—C15—C16—C17	1.3 (3)
C6—C2—C3—C4	125.53 (15)	C15—C16—C17—C18	0.9 (3)
C1—C2—C3—C4	14.91 (16)	C14—C13—C18—C17	0.3 (3)
N2—C3—C4—N1	−173.08 (14)	N1—C13—C18—C17	176.95 (17)
C2—C3—C4—N1	−8.67 (18)	C16—C17—C18—C13	−1.7 (3)
N2—C3—C4—S1	1.5 (2)	C3—C4—N1—C13	−156.00 (14)
C2—C3—C4—S1	165.92 (11)	S1—C4—N1—C13	29.5 (2)
O3—C2—C6—O1	−40.0 (3)	C3—C4—N1—C1	−2.30 (16)
C3—C2—C6—O1	90.4 (2)	S1—C4—N1—C1	−176.76 (11)
C1—C2—C6—O1	−161.1 (2)	C18—C13—N1—C4	39.6 (2)
O3—C2—C6—C7	136.79 (15)	C14—C13—N1—C4	−143.72 (16)
C3—C2—C6—C7	−92.78 (16)	C18—C13—N1—C1	−112.28 (17)
C1—C2—C6—C7	15.68 (18)	C14—C13—N1—C1	64.36 (19)
O1—C6—C7—C8	164.5 (2)	O2—C1—N1—C4	136.14 (13)
C2—C6—C7—C8	−12.2 (2)	C8—C1—N1—C4	−100.46 (14)
O1—C6—C7—C12	−10.3 (4)	C2—C1—N1—C4	11.43 (15)
C2—C6—C7—C12	173.0 (2)	O2—C1—N1—C13	−68.05 (16)
C12—C7—C8—C9	1.3 (3)	C8—C1—N1—C13	55.35 (17)
C6—C7—C8—C9	−173.89 (16)	C2—C1—N1—C13	167.24 (13)
C12—C7—C8—C1	178.35 (18)	C4—C3—N2—O4	−23.3 (2)
C6—C7—C8—C1	3.1 (2)	C2—C3—N2—O4	173.83 (16)
O2—C1—C8—C7	−116.54 (15)	C4—C3—N2—O5	158.10 (16)
N1—C1—C8—C7	118.47 (14)	C2—C3—N2—O5	−4.8 (2)
C2—C1—C8—C7	6.84 (17)	N1—C4—S1—C5	28.50 (16)
O2—C1—C8—C9	60.2 (2)	C3—C4—S1—C5	−145.23 (14)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C13–C18 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O5	0.82	2.34	2.895 (2)	126
O2—H2···O5ⁱ	0.82	2.00	2.8155 (18)	171
C11—H11···O4ⁱⁱ	0.93	2.51	3.423 (3)	166
C9—H9···Cg1	0.93	2.89	3.545 (2)	129

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C13–C18 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O5	0.82	2.34	2.895 (2)	126
O2—H2···O5ⁱ	0.82	2.00	2.8155 (18)	171
C11—H11···O4ⁱⁱ	0.93	2.51	3.423 (3)	166
C9—H9···Cg1	0.93	2.89	3.545 (2)	129

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

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

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Volume 69| Part 12| December 2013| Pages o1770-o1771

doi:10.1107/S1600536813029577

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

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

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organic compounds

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