(3aR,8bR)-3a,8b-Dihy-droxy-1-(4-meth-oxy-phen-yl)-2-methyl-sulfan-yl-3-nitro-1,8b-di-hydro-indeno-[1,2-b]pyrrol-4(3aH)-one.

In the title compound, C19H16N2O6S, the pyrrolidine ring adopts a twisted conformation with puckering parameters q 2 = 0.088 (3) Å and Φ2 = 61.5 (14)°. The cyclo-pentane ring adopts a twisted conformation with puckering parameters q 2 = 0.099 (2) Å and Φ2 = 242.8 (14)°. A weak intra-molecular O-H⋯O inter-action occurs. In the crystal, pairs of C-H⋯O inter-actions generate dimers with graph-set motif R 2 (2)(24) and they are interconnected by pairs of O-H⋯O hydrogen bonds, which link the mol-ecules into inversion dimers with graph-set motif R 2 (2)(10).

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 = 400.40

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.155

S = 1.02

3311 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.44 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813031279/zq2211sup1.cif

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813031279/zq2211Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H16N2O6S	F(000) = 832
Mr = 400.40	Dx = 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

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

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(Fo2) + (0.0989P)2 + 0.7209P] where P = (Fo2 + 2Fc2)/3
3311 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.44 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) ; (ii) .