(3aR,8bR)-3a,8b-Dihy-droxy-2-methyl-sulfanyl-3-nitro-1-phenyl-1,8b-di-hydro-indeno[1,2-b]pyrrol-4(3aH)-one.

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 cyclo-pentane 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 mol-ecular structure features a weak intra-molecular O-H⋯O bond and a possible C-H⋯π inter-action. In the crystal, the mol-ecules are linked into [010] chains by O-H⋯O hydrogen bonds. Weak C-H⋯O bonds connect the chains into (100) sheets.

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 = 370.37

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.092

S = 1.00

4140 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶)

Absolute structure parameter: 0.00 (6)

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/S1600536813029577/hb7154sup1.cif

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

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

C18H14N2O5S	F(000) = 768
Mr = 370.37	Dx = 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

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

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(Fo2) + (0.0557P)2 + 0.2428P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
4140 reflections	Δρmax = 0.23 e Å−3
236 parameters	Δρmin = −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)

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	0.14622 (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)

	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)

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)

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

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) ; (ii) .