Crystal structures of 6a,6b,7,11a-tetra­hydro-6H,9H-spiro­[chromeno[3′,4′:3,4]pyrrolo­[1,2-c]thia­zole-11,3′-indoline]-2′,6-dione and 5′-methyl-6a,6b,7,11a-tetra­hydro-6H,9H-spiro­[chromeno[3′,4′:3,4]pyrrolo­[1,2-c]thia­zole-11,3′-indoline]-2′,6-dione

Pangajavalli, S.; Ranjithkumar, R.; Srinivasan, N.; Ramaswamy, S.; Selvanayagam, S.

doi:10.1107/S2056989019000045

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 75| Part 2| February 2019| Pages 246-250

https://doi.org/10.1107/S2056989019000045

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Crystal structures of 6a,6b,7,11a-tetrahydro-6H,9H-spiro[chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazole-11,3′-indoline]-2′,6-dione and 5′-methyl-6a,6b,7,11a-tetrahydro-6H,9H-spiro[chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazole-11,3′-indoline]-2′,6-dione

S. Pangajavalli,^a ^* R. Ranjithkumar,^b N. Srinivasan,^c S. Ramaswamy ^d and S. Selvanayagam ^e ‡

^aDepartment of Physics, Sri S. Ramasamy Naidu Memorial College, Sattur 626 203, India, ^bSchool of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, ^cDepartment of Physics, Thiagarajar College, Madurai 625 009, India, ^dDepartment of Physics, N. M. S. S. Vellaichamy Nadar College, Madurai 625 019, India, and ^ePG & Research Department of Physics, Government Arts College, Melur 625 106, India
^*Correspondence e-mail: pangajam2015@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 6 December 2018; accepted 2 January 2019; online 22 January 2019)

The title compounds, C₂₀H₁₆N₂O₃S, (I), and C₂₁H₁₈N₂O₃S, (II), differ by the presence of a methyl group in position 5 on the 1H-indole-2-one ring of compound (II). The two compounds have a structural overlap r.m.s. deviation of 0.48 Å. There is a significant difference in the conformation of the thiazolidine ring: it has a twisted conformation on the fused N—C bond in (I), but an envelope conformation in compound (II) with the S atom as the flap. The planar pyrrolidine ring of the indole ring system is normal to the mean plane of the five-membered pyrrolidine ring of the pyrrolothiazole unit in both compounds, with dihedral angles of 88.71 (9) and 84.59 (8)°. The pyran rings in both structures have envelope conformations with the methylene C atom adjacent to the C=O group as the flap. In both compounds, there is a short intramolecular C—H⋯O contact present. In the crystal of (I), molecules are linked by C—H⋯O hydrogen bonds forming chains propagating along the b-axis direction. The chains are linked by N—H⋯π interactions, forming layers parallel to (10 $[\overline{1}]$ ). In the crystal of (II), molecules are linked by pairs of N—H⋯O hydrogen bonds, forming inversion dimers which are linked by C—H⋯O hydrogen bonds to form a three-dimensional structure.

Keywords: crystal structure; indole derivatives; pyrrolo; chromeno; spiro; thiazole; N—H⋯π interactions; C—H⋯π interactions; hydrogen bonding.

CCDC references: 1888373; 1888372

1. Chemical context

Indole derivatives have been reported to exhibit a large number of biological activities, such as anti-inflammatory (Chen et al., 2017 ), anti-fungal (Singh et al., 2000 ), anti-hepatitis B virus (Chai et al., 2006 ) and anti-HIV (Sriram et al., 2006 ; Pandeya et al., 2000 ). Indole analogues play a significant role in a diverse array of products, such as vitamin supplements, dyes, plastics, flavour enhancers, and in the agricultural and perfumery industries (Barden, 2011 ). In view of the importance of such compounds, we report herein on the synthesis and molecular and crystal structures of the title compounds, 6a,6b,7,11a-tetrahydro-6H,9H-spiro[chromeno[3′,4′:3,4]pyrrolo [1,2-c]thiazole-11,3′-indoline]-2′,6-dione (I) and 5′-methyl-6a,6b,7,11a-tetrahydro-6H,9H-spiro[chromeno[3′,4′:3,4]pyrrolo [1,2-c]thiazole-11,3′-indoline]-2′,6-dione (II).

2. Structural commentary

The molecular structure of compound (I) is illustrated in Fig. 1, and for compound (II) in Fig. 2. The conformations of the two molecules differ by an r.m.s. deviation of 0.48 Å, as shown in the structural overlap figure (Fig. 3). The molecular structures of both compounds are influenced by a short intramolecular C—H⋯O contact (Tables 1 and 2), which forms an S(5) ring motif (Figs. 1 and 2).

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

Cg is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O2	0.98	2.50	2.902 (2)	104
N2—H2⋯Cgⁱ	0.86	2.57	3.799 (18)	157
C8—H8⋯O2ⁱⁱ	0.98	2.38	3.321 (2)	160
C9—H9⋯O3ⁱⁱ	0.98	2.44	3.376 (2)	159
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O2	0.98	2.44	2.882 (2)	107
N2—H2⋯O3ⁱ	0.86	2.06	2.903 (2)	168
C3—H3⋯O1ⁱⁱ	0.93	2.55	3.302 (2)	139
C9—H9⋯O2ⁱⁱⁱ	0.98	2.59	3.320 (2)	131
C21—H21C⋯O2^iv	0.96	2.57	3.390 (2)	144
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x+1, -y+1, -z+1; (iii) -x, -y+1, -z+1; (iv) x, y, z-1.

Figure 1
A view of the molecular structure of compound (I)

, showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level. The intramolecular C—H⋯O interaction (Table 1

) is shown as a dashed line.

Figure 2
A view of the molecular structure of compound (II)

, showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level. The intramolecular C—H⋯O interaction (Table 2

) is shown as a dashed line.

Figure 3
Structural overlay of compound (I)

(purple) and compound (II)

(red). The r.m.s. deviation is 0.48 Å (Mercury; Macrae et al., 2008

There is a significant difference in the conformation of the five-membered thiazolidine ring in the two compounds. In compound (I), the thiazolidine ring (S1/N1/C10–C12) adopts a twist conformation on the N1—C10 bond [ΔC₂(S1) asymmetry parameter is 0.006 (1)]. In (II) this ring adopts an envelope conformation [puckering parameters q₂ = 0.529 (2) Å and φ = 105.8 (1)°] with atom S1 as the flap, deviating by 0.896 (1) Å from the mean plane through the remaining four atoms.

In compound (I), the pyrrolidine ring (C8–C10/N1/C13) adopts an envelope conformation [puckering parameters q₂ = 0.335 (2) Å and φ = 39.4 (1)°] with atom C9 as the flap, deviating by 0.518 (2) Å from the mean plane through the remaining four atoms. In (II) this ring adopts a twist conformation on the C8—C13 bond [ΔC₂(C10) asymmetry parameter is 0.005 (1)].

The 2,3-dihydro-1H-indol-2-one ring is planar in both compounds, with a maximum deviation of 0.054 (1) and 0.080 (1) Å from the mean plane for atom C14 in (I) and (II), respectively. Oxygen atom O3 of this ring deviates by 0.151 (1) and 0.185 (1) Å, respectively, from the above mean planes. The methyl atom C21 in (II) deviates by 0.056 (2) Å from the plane of the benzene ring to which it is attached.

The pyran rings (C1/O1/C2/C7–C9) in both structures have distorted sofa conformations, with ΔC_s(C2) asymmetry parameters (Nardelli, 1983 ) of 0.005 (1) and 0.006 (1), respectively. Atom C9 deviates from the mean plane through the remaining five atoms (O1/C1/C2/C7/C8) of the pyran ring by 0.465 (2) Å in (I) and by 0.383 (2) Å in (II).

In both compounds, the planar pyrrolidine ring (N2/C13–C15/C20) of the indole ring system is normal to the mean plane of the pyrrolidine ring (N1/C8–C10/C13) of the pyrrolothiazole unit, with a dihedral angle of 88.71 (9)° for (I) and 84.59 (8)° for (II). The mean plane of the pyrrolidine ring (N1/C8–C10/C13) is inclined to the mean plane of the thiazolidine ring (S1/N1/C10–C12) by 64.39 (2)° in (I) and 79.51 (9)° in (II).

3. Supramolecular features

In the crystal of compound (I), molecules associate via two C—H⋯O intermolecular interactions (C8—H8⋯O2ⁱⁱ, C9—H9⋯O3ⁱⁱ, Table 1) forming chains propagating along [001]; see Fig. 4. In addition to this, inversion-related molecules are linked to form dimers by N—H⋯π interactions; N2—H2⋯Cgⁱ, where Cg is the centroid of the benzene ring (C2–C7); see Fig. 4 and Table 1. The result of these interactions is the formation of layers lying parallel to the (10 $[\overline{1}]$ ) plane.

Figure 4
The crystal packing of compound (I)

viewed along the a axis. The C—H⋯O hydrogen bonds (see Table 1

) are shown as dashed lines, while the N—H⋯π interactions are shown as orange arrows. For clarity, H atoms not involved in these interactions have been omitted.

In the crystal of compound (II), molecules are linked via pairs of N—H⋯O hydrogen bonds (N2—H2⋯O3ⁱ, Table 2), forming inversion dimers with an R₂²(8) ring motif (Fig. 5). There are two pairs of weak C—H⋯O intermolecular interactions (C3—H3⋯O1ⁱⁱ, C9—H9⋯O2ⁱⁱⁱ, Table 2) also forming inversion dimers and enclosing R₂²(8) ring motifs. These dimers are linked to form a helix along the a-axis direction. A further C—H⋯O hydrogen bond (C21—H21C⋯O2^iv, Table 2) links the molecules to form C(10) chains propagating along [010] in an anti-parallel manner. As a result of the various N—H⋯O and C—H⋯O hydrogen bonds, a three-dimensional structure is formed (Table 2 and Fig. 5)

Figure 5
The crystal packing of compound (II)

viewed along the a axis. The N—H⋯O and C—H⋯O hydrogen bonds (Table 2

) are shown as dashed lines. For clarity, H atoms not involved in the hydrogen bonds have been omitted.

4. Database survey

A search of the Cambridge Structural Database (Version 5.39, last update August 2018; Groom et al., 2016 ) for partial structure S1 (Fig. 6) gave three hits. Details are given in the supporting information (CSD search S1). They include: 2,4-dichloro-5′-methyl-6a,6b,7,8,9,11a-hexahydro-6H-spiro[chromeno[3,4-a]pyrrolizine-11,3′-indole]-2′,6(1′H)-dione monohydrate (GUCGIN; Kanchithalaivan et al., 2014a ), 3a-acetyl-2-methyl-2,3,3a,9b-tetrahydro-4H-spiro[chromeno[3,4-c]pyrrole-1,3′-indole]-2′,4(1′H)-dione (SUTLAV; Ghandi et al., 2010 ), and 8-bromo-2-methyl-2,3,3a,9b-tetrahydro-4H-spiro[chromeno[3,4-c]pyrrole-1,3′-indole]-2′,4(1′H)-dione (SUTLEZ; Ghandi et al., 2010). Here the dihedral angle between the planar pyrrolidine ring of the indole ring system and the mean plane of the pyrrolidine ring of the pyrrolothiazole unit are 82.85, 87.66 and 86.60°, respectively, compared to 88.71 (9)° in (I) and 84.59 (8)° in (II).

Figure 6
Partial structures for the CSD database searches.

A search for partial structure S2 (Fig. 6) gave 23 hits. Details are given in in the supporting information (CSD search S2). In these structures, the dihedral angle between the planar pyrrolidine ring of the indole ring system and the mean plane of the pyrrolidine ring of the pyrrolothiazole unit varies from 77.60° in 1′-phenyl-6′-thiacycloheptane-1-spiro-2′-perhydropyrrolizine-3′-spiro-3′′-indoline-2,2′′-dione (GITDOD; Sundaramoorthy et al., 2008 ) to 89.72° in 3-hydroxy-10,13-dimethyl-7′-(4-methylphenyl)-1,3,4,5,6,7,7′,7a′,8,9,10,11,12,13,14,15-hexadecahydro-1′H-dispiro[cyclopenta[a]phenanthrene-16,6′-pyrrolo[1,2-c][1,3]thiazole-5′,3′′-indole]-2′′,17(1′′H,2H)-dione (MUDLAA; Kanchithalaivan et al., 2014b ). Only four of these compounds are monospiro, the others, like the two above, have a dispiro arrangement. The four compounds are 7′-(2-chlorophenyl)-6′-(pyridin-2-ylcarbonyl)-1′,6′,7′,7a′-tetrahydrospiro[indole-3,5′-pyrrolo[1,2-c][1,3]thiazol]-2(1H)-one ethanol solvate (GUCHET; Li et al., 2014 ), ethyl 7′-(6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-oxo-1,1′,2,6′,7′,7a′-hexahydrospiro[indole-3,5′-pyrrolo[1,2-c][1,3]thiazole]-6′-carboxylate (NUHHIJ; Suhitha et al., 2013 ), ethyl 2-oxo-7′-(2,2,7,7-tetramethyltetrahydro-3aH-bis[1,3]dioxolo[4,5-b:4′,5′-d]pyran-5-yl)-1,1′,2,6′,7′,7a′-hexahydrospiro[indole-3,5′-pyrrolo[1,2-c][1,3]thiazole]-6′-carboxylate monohydrate (SUWNEE; Prasanna et al., 2010 ) and 6′-benzoyl-7′-(4-chlorophenyl)-3′-phenyl-1′,6′,7′,7a′-tetrahydrospiro[indole-3,5′-pyrrolo[1,2-c][1,3]thiazol]-2(1H)-one (XEVGIQ; Kumar et al., 2013 ). Here the dihedral angles between the planar pyrrolidine ring of the indole ring system and the mean plane of the pyrrolidine ring of the pyrrolothiazole unit are 79.94, 87.79, 84.78 and 81.44°, respectively, compared to 88.71 (9)° in (I) and 84.59 (8)° in (II).

5. Synthesis and crystallization

Compound (I): A flask containing salicylaldehyde (1 mmol) and 2,2-dimethyl-1,3-dioxane-4,6-dione (1 mmol) in water (7 ml) was placed at the maximum energy area in an ultrasonic cleaner and the surface of the reactants was placed slightly lower than the level of the water. The mixture was subjected to ultrasonic irradiation of low power at 323 K for ca 30 min. To this, a mixture of isatin (1 mmol) and 1,3-thiazolane-4-carboxylic acid (1 mmol) dissolved in methanol (7 ml) was added. The irradiation was continued until the completion of the reaction (ca 50 min), during which time the product precipitated from the reaction mixture. It was then filtered and dried to obtain the pure product. The compound was further recrystallized from an ethanol–ethyl acetate mixture (1:1) to obtain colourless block-like crystals.

Compound (II): A flask containing salicylaldehyde (1 mmol) and 2,2-dimethyl-1,3-dioxane-4,6-dione (1 mmol) in water (7 ml) was placed at the maximum energy area in an ultrasonic cleaner and the surface of the reactants was placed slightly lower than the level of the water. The mixture was subjected to ultrasonic irradiation of low power at 323 K for about 30 min. To this, a mixture of 5-methylisatin (1 mmol) and 1,3-thiazolane-4-carboxylic acid (1 mmol) dissolved in methanol (7 ml) was added. The irradiation was continued until the completion of the reaction (ca 45 min), during which time the product precipitated from the reaction mixture. It was then filtered and dried to obtain the pure product. The compound was further recrystallized from ethyl acetate to obtain colourless block-like crystals.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. For both compounds, the H atoms were placed in idealized positions and allowed to ride on their parent atoms: N—H = 0.86 Å and C—H = 0.93–0.97 Å, with U_iso(H) = 1.5U_eq(C-methyl) and 1.2U_eq(N, C) for other H atoms.

Table 3
Experimental details

	(I)	(II)
Crystal data
Chemical formula	C₂₀H₁₆N₂O₃S	C₂₁H₁₈N₂O₃S
M_r	364.41	378.43
Crystal system, space group	Monoclinic, P2₁/n	Triclinic, P $[\overline{1}]$
Temperature (K)	298	298
a, b, c (Å)	11.3058 (9), 10.0905 (8), 15.1957 (12)	8.3648 (5), 9.7648 (6), 11.9677 (7)
α, β, γ (°)	90, 101.072 (1), 90	112.622 (1), 99.388 (1), 91.885 (1)
V (Å³)	1701.3 (2)	885.31 (9)
Z	4	2
Radiation type	Mo Kα	Mo Kα
μ (mm⁻¹)	0.21	0.21
Crystal size (mm)	0.21 × 0.18 × 0.16	0.22 × 0.19 × 0.17

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector	Bruker SMART APEX CCD area-detector
No. of measured, independent and observed [I > 2σ(I)] reflections	19453, 4146, 3646	10444, 4164, 3747
R_int	0.023	0.016
(sin θ/λ)_max (Å⁻¹)	0.668	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.141, 1.02	0.048, 0.140, 1.05
No. of reflections	4146	4164
No. of parameters	235	245
No. of restraints	1	0
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.37	0.67, −0.58
Computer programs: SMART and SAINT (Bruker, 2002 ), SHELXS97 (Sheldrick, 2008 ), SHELXL2018 (Sheldrick, 2015 ), PLATON (Spek, 2009 ), Mercury (Macrae et al., 2008 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC references: 1888373; 1888372

Crystal structure: contains datablocks I, II, global. DOI: https://doi.org/10.1107/S2056989019000045/su5467sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019000045/su5467Isup2.hkl

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989019000045/su5467IIsup3.hkl

CSD search S1. DOI: https://doi.org/10.1107/S2056989019000045/su5467sup4.pdf

CSD search S2. DOI: https://doi.org/10.1107/S2056989019000045/su5467sup5.pdf

checkCIF report

Computing details top

For both structures, data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

6a,6b,7,11a-Tetrahydro-6H,9H-spiro[chromeno[3',4':3,4]pyrrolo[1,2-c]thiazole-11,3'-indoline]-2',6-dione (I) top

Crystal data top

C₂₀H₁₆N₂O₃S	F(000) = 760
M_r = 364.41	D_x = 1.423 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.3058 (9) Å	Cell parameters from 11828 reflections
b = 10.0905 (8) Å	θ = 2.4–27.6°
c = 15.1957 (12) Å	µ = 0.21 mm⁻¹
β = 101.072 (1)°	T = 298 K
V = 1701.3 (2) Å³	Block, colourless
Z = 4	0.21 × 0.18 × 0.16 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	R_int = 0.023
Radiation source: fine-focus sealed tube	θ_max = 28.4°, θ_min = 2.1°
ω and φ scans	h = −15→15
19453 measured reflections	k = −13→13
4146 independent reflections	l = −19→20
3646 reflections with I > 2σ(I)

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0749P)² + 0.6691P] where P = (F_o² + 2F_c²)/3
4146 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.65 e Å⁻³
1 restraint	Δρ_min = −0.37 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

	x	y	z	U_iso*/U_eq
S1	0.57371 (5)	0.86992 (6)	0.95071 (3)	0.06229 (18)
O1	0.84530 (11)	0.85243 (14)	0.62287 (8)	0.0483 (3)
O2	0.91582 (12)	0.96789 (15)	0.74380 (10)	0.0580 (4)
O3	0.63036 (12)	1.05167 (12)	0.61274 (9)	0.0491 (3)
N1	0.61304 (11)	0.95792 (13)	0.79329 (8)	0.0363 (3)
N2	0.42770 (14)	1.00915 (16)	0.59558 (11)	0.0510 (4)
H2	0.401330	1.064837	0.553539	0.061*
C1	0.84352 (14)	0.88731 (17)	0.70943 (12)	0.0414 (4)
C2	0.75317 (15)	0.77756 (17)	0.57221 (11)	0.0413 (4)
C3	0.77089 (19)	0.7398 (2)	0.48794 (13)	0.0545 (5)
H3	0.842381	0.760585	0.469330	0.065*
C4	0.6811 (2)	0.6711 (2)	0.43215 (13)	0.0619 (5)
H4	0.692571	0.644363	0.375835	0.074*
C5	0.5742 (2)	0.6417 (2)	0.45907 (13)	0.0585 (5)
H5	0.512648	0.598674	0.420168	0.070*
C6	0.55927 (18)	0.67675 (18)	0.54432 (13)	0.0496 (4)
H6	0.487889	0.655046	0.562774	0.060*
C7	0.64923 (15)	0.74391 (15)	0.60294 (11)	0.0383 (3)
C8	0.63887 (13)	0.77552 (15)	0.69741 (10)	0.0351 (3)
H8	0.608885	0.695840	0.722794	0.042*
C9	0.75974 (14)	0.81137 (16)	0.75678 (10)	0.0382 (3)
H9	0.799982	0.729271	0.780519	0.046*
C10	0.72344 (14)	0.88742 (18)	0.83418 (10)	0.0417 (4)
H10	0.786632	0.950538	0.859742	0.050*
C11	0.6941 (2)	0.7942 (2)	0.90799 (13)	0.0611 (6)
H11A	0.764283	0.783469	0.955452	0.073*
H11B	0.669905	0.707638	0.883100	0.073*
C12	0.54452 (15)	0.99367 (18)	0.86045 (11)	0.0433 (4)
H12A	0.459238	0.995734	0.834284	0.052*
H12B	0.568283	1.080964	0.884175	0.052*
C13	0.55309 (13)	0.89158 (14)	0.70978 (10)	0.0325 (3)
C14	0.54547 (15)	0.99491 (15)	0.63379 (10)	0.0375 (3)
C15	0.35371 (15)	0.92197 (19)	0.63287 (12)	0.0465 (4)
C16	0.23026 (18)	0.9034 (3)	0.60850 (16)	0.0679 (6)
H16	0.183914	0.953834	0.563437	0.081*
C17	0.17892 (19)	0.8076 (3)	0.65336 (18)	0.0767 (8)
H17	0.096136	0.793850	0.638706	0.092*
C18	0.2469 (2)	0.7318 (3)	0.71934 (17)	0.0718 (7)
H18	0.209658	0.666702	0.747758	0.086*
C19	0.37089 (18)	0.7509 (2)	0.74433 (13)	0.0547 (5)
H19	0.417048	0.699062	0.788679	0.066*
C20	0.42334 (14)	0.84931 (17)	0.70121 (10)	0.0391 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0646 (3)	0.0793 (4)	0.0497 (3)	0.0140 (3)	0.0277 (2)	0.0133 (2)
O1	0.0390 (6)	0.0624 (8)	0.0475 (7)	0.0000 (5)	0.0180 (5)	0.0005 (6)
O2	0.0435 (7)	0.0635 (8)	0.0679 (9)	−0.0092 (6)	0.0132 (6)	−0.0084 (7)
O3	0.0530 (7)	0.0456 (7)	0.0512 (7)	−0.0028 (5)	0.0164 (5)	0.0105 (5)
N1	0.0341 (6)	0.0409 (7)	0.0333 (6)	0.0016 (5)	0.0047 (5)	−0.0035 (5)
N2	0.0463 (8)	0.0557 (9)	0.0473 (8)	0.0107 (7)	−0.0002 (6)	0.0104 (7)
C1	0.0321 (7)	0.0452 (9)	0.0481 (9)	0.0056 (6)	0.0107 (6)	0.0017 (7)
C2	0.0430 (8)	0.0418 (8)	0.0405 (8)	0.0097 (7)	0.0115 (7)	0.0029 (6)
C3	0.0605 (11)	0.0619 (11)	0.0458 (9)	0.0179 (9)	0.0218 (8)	0.0045 (8)
C4	0.0869 (15)	0.0603 (12)	0.0398 (9)	0.0177 (11)	0.0152 (9)	−0.0056 (8)
C5	0.0756 (14)	0.0496 (10)	0.0463 (10)	0.0016 (9)	0.0017 (9)	−0.0086 (8)
C6	0.0549 (10)	0.0423 (9)	0.0512 (10)	−0.0011 (8)	0.0090 (8)	−0.0056 (7)
C7	0.0443 (8)	0.0322 (7)	0.0394 (8)	0.0060 (6)	0.0105 (6)	−0.0008 (6)
C8	0.0366 (7)	0.0314 (7)	0.0388 (7)	0.0015 (6)	0.0111 (6)	0.0026 (6)
C9	0.0357 (7)	0.0418 (8)	0.0376 (7)	0.0066 (6)	0.0081 (6)	0.0046 (6)
C10	0.0334 (7)	0.0560 (10)	0.0352 (8)	0.0038 (7)	0.0053 (6)	−0.0002 (7)
C11	0.0646 (12)	0.0792 (14)	0.0438 (9)	0.0259 (11)	0.0210 (9)	0.0182 (9)
C12	0.0431 (8)	0.0475 (9)	0.0399 (8)	0.0052 (7)	0.0090 (6)	−0.0078 (7)
C13	0.0313 (7)	0.0341 (7)	0.0328 (7)	−0.0005 (5)	0.0079 (5)	−0.0005 (5)
C14	0.0419 (8)	0.0348 (7)	0.0362 (7)	0.0040 (6)	0.0087 (6)	−0.0006 (6)
C15	0.0356 (8)	0.0571 (10)	0.0457 (9)	0.0043 (7)	0.0054 (7)	−0.0124 (8)
C16	0.0381 (10)	0.0904 (16)	0.0697 (13)	0.0066 (10)	−0.0029 (9)	−0.0207 (12)
C17	0.0366 (10)	0.111 (2)	0.0841 (16)	−0.0196 (12)	0.0150 (10)	−0.0381 (15)
C18	0.0551 (12)	0.0933 (17)	0.0739 (14)	−0.0346 (12)	0.0293 (11)	−0.0258 (13)
C19	0.0510 (10)	0.0648 (12)	0.0519 (10)	−0.0176 (9)	0.0192 (8)	−0.0071 (9)
C20	0.0332 (7)	0.0479 (9)	0.0379 (8)	−0.0037 (6)	0.0108 (6)	−0.0097 (6)

Geometric parameters (Å, º) top

S1—C11	1.789 (2)	C8—C9	1.529 (2)
S1—C12	1.8373 (19)	C8—C13	1.555 (2)
O1—C1	1.366 (2)	C8—H8	0.9800
O1—C2	1.393 (2)	C9—C10	1.525 (2)
O2—C1	1.199 (2)	C9—H9	0.9800
O3—C14	1.212 (2)	C10—C11	1.548 (3)
N1—C12	1.441 (2)	C10—H10	0.9800
N1—C10	1.467 (2)	C11—H11A	0.9700
N1—C13	1.4791 (19)	C11—H11B	0.9700
N2—C14	1.354 (2)	C12—H12A	0.9700
N2—C15	1.406 (3)	C12—H12B	0.9700
N2—H2	0.8600	C13—C20	1.509 (2)
C1—C9	1.505 (2)	C13—C14	1.546 (2)
C2—C3	1.387 (2)	C15—C20	1.386 (3)
C2—C7	1.387 (2)	C15—C16	1.386 (3)
C3—C4	1.378 (3)	C16—C17	1.374 (4)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.380 (3)	C17—C18	1.373 (4)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.384 (3)	C18—C19	1.394 (3)
C5—H5	0.9300	C18—H18	0.9300
C6—C7	1.393 (2)	C19—C20	1.384 (3)
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.497 (2)

C11—S1—C12	93.42 (8)	C9—C10—C11	112.32 (15)
C1—O1—C2	121.62 (13)	N1—C10—H10	110.4
C12—N1—C10	110.55 (12)	C9—C10—H10	110.4
C12—N1—C13	120.07 (13)	C11—C10—H10	110.4
C10—N1—C13	110.87 (12)	C10—C11—S1	106.68 (13)
C14—N2—C15	111.89 (14)	C10—C11—H11A	110.4
C14—N2—H2	124.1	S1—C11—H11A	110.4
C15—N2—H2	124.1	C10—C11—H11B	110.4
O2—C1—O1	117.34 (16)	S1—C11—H11B	110.4
O2—C1—C9	125.18 (17)	H11A—C11—H11B	108.6
O1—C1—C9	117.17 (15)	N1—C12—S1	108.34 (11)
C3—C2—C7	121.70 (17)	N1—C12—H12A	110.0
C3—C2—O1	115.71 (16)	S1—C12—H12A	110.0
C7—C2—O1	122.58 (14)	N1—C12—H12B	110.0
C4—C3—C2	119.08 (19)	S1—C12—H12B	110.0
C4—C3—H3	120.5	H12A—C12—H12B	108.4
C2—C3—H3	120.5	N1—C13—C20	118.66 (12)
C3—C4—C5	120.61 (18)	N1—C13—C14	106.63 (12)
C3—C4—H4	119.7	C20—C13—C14	102.26 (12)
C5—C4—H4	119.7	N1—C13—C8	104.53 (11)
C4—C5—C6	119.59 (19)	C20—C13—C8	113.28 (12)
C4—C5—H5	120.2	C14—C13—C8	111.37 (12)
C6—C5—H5	120.2	O3—C14—N2	126.85 (16)
C5—C6—C7	121.16 (19)	O3—C14—C13	125.62 (14)
C5—C6—H6	119.4	N2—C14—C13	107.52 (14)
C7—C6—H6	119.4	C20—C15—C16	121.8 (2)
C2—C7—C6	117.74 (16)	C20—C15—N2	109.67 (14)
C2—C7—C8	119.86 (15)	C16—C15—N2	128.57 (19)
C6—C7—C8	122.36 (15)	C17—C16—C15	117.5 (2)
C7—C8—C9	112.99 (13)	C17—C16—H16	121.2
C7—C8—C13	116.23 (12)	C15—C16—H16	121.2
C9—C8—C13	104.95 (12)	C18—C17—C16	121.6 (2)
C7—C8—H8	107.4	C18—C17—H17	119.2
C9—C8—H8	107.4	C16—C17—H17	119.2
C13—C8—H8	107.4	C17—C18—C19	121.0 (2)
C1—C9—C10	113.58 (14)	C17—C18—H18	119.5
C1—C9—C8	114.30 (13)	C19—C18—H18	119.5
C10—C9—C8	103.39 (12)	C20—C19—C18	118.0 (2)
C1—C9—H9	108.4	C20—C19—H19	121.0
C10—C9—H9	108.4	C18—C19—H19	121.0
C8—C9—H9	108.4	C19—C20—C15	120.05 (16)
N1—C10—C9	104.51 (12)	C19—C20—C13	131.26 (16)
N1—C10—C11	108.58 (13)	C15—C20—C13	108.54 (14)

C2—O1—C1—O2	−168.97 (15)	C11—S1—C12—N1	9.94 (14)
C2—O1—C1—C9	17.2 (2)	C12—N1—C13—C20	−6.6 (2)
C1—O1—C2—C3	−174.90 (15)	C10—N1—C13—C20	124.34 (15)
C1—O1—C2—C7	6.0 (2)	C12—N1—C13—C14	108.01 (15)
C7—C2—C3—C4	2.3 (3)	C10—N1—C13—C14	−121.09 (13)
O1—C2—C3—C4	−176.83 (16)	C12—N1—C13—C8	−133.94 (14)
C2—C3—C4—C5	0.9 (3)	C10—N1—C13—C8	−3.04 (15)
C3—C4—C5—C6	−2.7 (3)	C7—C8—C13—N1	−143.84 (13)
C4—C5—C6—C7	1.4 (3)	C9—C8—C13—N1	−18.23 (15)
C3—C2—C7—C6	−3.5 (3)	C7—C8—C13—C20	85.55 (16)
O1—C2—C7—C6	175.57 (15)	C9—C8—C13—C20	−148.84 (12)
C3—C2—C7—C8	174.22 (15)	C7—C8—C13—C14	−29.07 (18)
O1—C2—C7—C8	−6.7 (2)	C9—C8—C13—C14	96.54 (14)
C5—C6—C7—C2	1.6 (3)	C15—N2—C14—O3	176.23 (16)
C5—C6—C7—C8	−176.06 (17)	C15—N2—C14—C13	−3.47 (19)
C2—C7—C8—C9	−14.6 (2)	N1—C13—C14—O3	58.27 (19)
C6—C7—C8—C9	162.98 (15)	C20—C13—C14—O3	−176.48 (15)
C2—C7—C8—C13	106.78 (17)	C8—C13—C14—O3	−55.2 (2)
C6—C7—C8—C13	−75.59 (19)	N1—C13—C14—N2	−122.03 (14)
O2—C1—C9—C10	30.5 (2)	C20—C13—C14—N2	3.23 (16)
O1—C1—C9—C10	−156.16 (14)	C8—C13—C14—N2	124.51 (14)
O2—C1—C9—C8	148.82 (17)	C14—N2—C15—C20	2.3 (2)
O1—C1—C9—C8	−37.8 (2)	C14—N2—C15—C16	−176.71 (19)
C7—C8—C9—C1	35.47 (18)	C20—C15—C16—C17	−1.4 (3)
C13—C8—C9—C1	−92.13 (15)	N2—C15—C16—C17	177.50 (19)
C7—C8—C9—C10	159.44 (13)	C15—C16—C17—C18	−0.7 (3)
C13—C8—C9—C10	31.84 (15)	C16—C17—C18—C19	1.1 (4)
C12—N1—C10—C9	158.83 (13)	C17—C18—C19—C20	0.5 (3)
C13—N1—C10—C9	23.14 (17)	C18—C19—C20—C15	−2.5 (3)
C12—N1—C10—C11	38.78 (19)	C18—C19—C20—C13	−177.54 (17)
C13—N1—C10—C11	−96.91 (16)	C16—C15—C20—C19	3.0 (3)
C1—C9—C10—N1	90.83 (16)	N2—C15—C20—C19	−176.04 (16)
C8—C9—C10—N1	−33.61 (16)	C16—C15—C20—C13	179.08 (17)
C1—C9—C10—C11	−151.65 (15)	N2—C15—C20—C13	0.01 (18)
C8—C9—C10—C11	83.91 (16)	N1—C13—C20—C19	−69.5 (2)
N1—C10—C11—S1	−29.53 (19)	C14—C13—C20—C19	173.54 (17)
C9—C10—C11—S1	−144.59 (13)	C8—C13—C20—C19	53.6 (2)
C12—S1—C11—C10	11.05 (16)	N1—C13—C20—C15	115.00 (15)
C10—N1—C12—S1	−29.65 (16)	C14—C13—C20—C15	−1.91 (16)
C13—N1—C12—S1	101.39 (14)	C8—C13—C20—C15	−121.87 (14)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2	0.98	2.50	2.902 (2)	104
N2—H2···Cgⁱ	0.86	2.57	3.799 (18)	157
C8—H8···O2ⁱⁱ	0.98	2.38	3.321 (2)	160
C9—H9···O3ⁱⁱ	0.98	2.44	3.376 (2)	159

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+3/2, y−1/2, −z+3/2.

5'-Methyl-6a,6b,7,11a-tetrahydro-6H,9H-spiro[chromeno[3',4':3,4]pyrrolo[1,2-c]thiazole-11,3'-indoline]-2',6-dione (II) top

Crystal data top

C₂₁H₁₈N₂O₃S	Z = 2
M_r = 378.43	F(000) = 396
Triclinic, P1	D_x = 1.420 Mg m⁻³
a = 8.3648 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.7648 (6) Å	Cell parameters from 7888 reflections
c = 11.9677 (7) Å	θ = 1.9–27.2°
α = 112.622 (1)°	µ = 0.21 mm⁻¹
β = 99.388 (1)°	T = 298 K
γ = 91.885 (1)°	Block, colourless
V = 885.31 (9) Å³	0.22 × 0.19 × 0.17 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	R_int = 0.016
Radiation source: fine-focus sealed tube	θ_max = 28.3°, θ_min = 1.9°
ω and φ scans	h = −11→10
10444 measured reflections	k = −12→12
4164 independent reflections	l = −15→15
3747 reflections with I > 2σ(I)

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.140	w = 1/[σ²(F_o²) + (0.0815P)² + 0.2689P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
4164 reflections	Δρ_max = 0.67 e Å⁻³
245 parameters	Δρ_min = −0.58 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
S1	−0.29132 (5)	0.74000 (6)	0.23215 (5)	0.06325 (18)
O1	0.28203 (16)	0.52624 (15)	0.43732 (11)	0.0523 (3)
O2	0.13654 (18)	0.64554 (16)	0.57307 (11)	0.0577 (3)
O3	0.33381 (14)	0.85985 (13)	0.48566 (10)	0.0430 (3)
N1	0.00582 (14)	0.86415 (13)	0.35425 (11)	0.0349 (3)
N2	0.38289 (15)	0.95200 (14)	0.34299 (12)	0.0385 (3)
H2	0.470194	1.010156	0.384421	0.046*
C1	0.1543 (2)	0.60502 (18)	0.46820 (14)	0.0429 (3)
C2	0.3272 (2)	0.48986 (17)	0.32294 (14)	0.0412 (3)
C3	0.4559 (2)	0.4032 (2)	0.30405 (18)	0.0530 (4)
H3	0.504909	0.372078	0.364539	0.064*
C4	0.5103 (2)	0.3637 (2)	0.19411 (19)	0.0543 (4)
H4	0.597736	0.306867	0.180813	0.065*
C5	0.4360 (2)	0.4081 (2)	0.10393 (18)	0.0516 (4)
H5	0.472276	0.380135	0.029583	0.062*
C6	0.3071 (2)	0.49431 (17)	0.12417 (15)	0.0415 (3)
H6	0.257290	0.523540	0.062749	0.050*
C7	0.25060 (17)	0.53824 (15)	0.23529 (13)	0.0344 (3)
C8	0.10802 (17)	0.62702 (14)	0.25841 (12)	0.0304 (3)
H8	0.022930	0.584116	0.184089	0.037*
C9	0.03505 (18)	0.62333 (16)	0.36667 (12)	0.0342 (3)
H9	−0.050188	0.539144	0.334102	0.041*
C10	−0.04772 (19)	0.76820 (17)	0.41498 (13)	0.0384 (3)
H10	−0.011738	0.818793	0.504508	0.046*
C11	−0.2345 (2)	0.7416 (2)	0.3835 (2)	0.0562 (5)
H11A	−0.281609	0.820745	0.442410	0.067*
H11B	−0.271795	0.647102	0.384579	0.067*
C12	−0.1351 (2)	0.8969 (2)	0.28430 (17)	0.0490 (4)
H12A	−0.105957	0.911235	0.214080	0.059*
H12B	−0.175301	0.987402	0.335626	0.059*
C13	0.13847 (16)	0.79580 (15)	0.28968 (12)	0.0310 (3)
C14	0.29735 (17)	0.87016 (15)	0.38586 (13)	0.0338 (3)
C15	0.31155 (17)	0.93035 (16)	0.22215 (14)	0.0355 (3)
C16	0.3694 (2)	0.98465 (19)	0.14429 (16)	0.0463 (4)
H16	0.466289	1.047091	0.169880	0.056*
C17	0.2784 (2)	0.94312 (19)	0.02629 (16)	0.0470 (4)
H17	0.315011	0.980334	−0.026878	0.056*
C18	0.1343 (2)	0.84777 (16)	−0.01552 (14)	0.0398 (3)
C19	0.07923 (19)	0.79402 (15)	0.06572 (13)	0.0365 (3)
H19	−0.015862	0.729181	0.039691	0.044*
C20	0.16607 (17)	0.83718 (14)	0.18489 (13)	0.0321 (3)
C21	0.0385 (3)	0.8044 (2)	−0.14405 (15)	0.0522 (4)
H21A	−0.023462	0.884117	−0.147536	0.078*
H21B	−0.034059	0.716052	−0.165745	0.078*
H21C	0.111978	0.785222	−0.200908	0.078*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0352 (2)	0.0722 (3)	0.0593 (3)	0.0004 (2)	−0.00072 (19)	0.0054 (2)
O1	0.0604 (8)	0.0633 (8)	0.0366 (6)	0.0138 (6)	0.0050 (5)	0.0245 (6)
O2	0.0719 (9)	0.0725 (9)	0.0334 (6)	0.0018 (7)	0.0122 (6)	0.0255 (6)
O3	0.0408 (6)	0.0495 (6)	0.0329 (5)	−0.0105 (5)	−0.0009 (4)	0.0144 (5)
N1	0.0321 (6)	0.0334 (6)	0.0370 (6)	−0.0014 (4)	0.0093 (5)	0.0109 (5)
N2	0.0311 (6)	0.0413 (7)	0.0378 (6)	−0.0093 (5)	0.0043 (5)	0.0120 (5)
C1	0.0512 (9)	0.0462 (8)	0.0328 (7)	−0.0035 (7)	0.0057 (6)	0.0188 (6)
C2	0.0433 (8)	0.0394 (7)	0.0361 (7)	0.0003 (6)	0.0026 (6)	0.0120 (6)
C3	0.0510 (10)	0.0467 (9)	0.0545 (10)	0.0085 (7)	−0.0017 (8)	0.0171 (8)
C4	0.0463 (9)	0.0441 (9)	0.0646 (11)	0.0098 (7)	0.0112 (8)	0.0124 (8)
C5	0.0528 (10)	0.0450 (9)	0.0531 (10)	0.0035 (7)	0.0211 (8)	0.0110 (7)
C6	0.0462 (8)	0.0383 (7)	0.0386 (8)	0.0020 (6)	0.0115 (6)	0.0126 (6)
C7	0.0361 (7)	0.0298 (6)	0.0330 (7)	−0.0029 (5)	0.0047 (5)	0.0091 (5)
C8	0.0335 (6)	0.0303 (6)	0.0254 (6)	−0.0037 (5)	0.0041 (5)	0.0100 (5)
C9	0.0385 (7)	0.0351 (7)	0.0280 (6)	−0.0053 (5)	0.0070 (5)	0.0118 (5)
C10	0.0426 (8)	0.0384 (7)	0.0312 (7)	−0.0027 (6)	0.0121 (6)	0.0093 (6)
C11	0.0434 (9)	0.0535 (10)	0.0752 (13)	0.0006 (7)	0.0276 (9)	0.0233 (9)
C12	0.0419 (8)	0.0568 (10)	0.0570 (10)	0.0120 (7)	0.0164 (7)	0.0286 (8)
C13	0.0302 (6)	0.0305 (6)	0.0295 (6)	−0.0040 (5)	0.0048 (5)	0.0097 (5)
C14	0.0306 (6)	0.0315 (6)	0.0338 (7)	−0.0028 (5)	0.0062 (5)	0.0073 (5)
C15	0.0343 (7)	0.0340 (7)	0.0376 (7)	−0.0003 (5)	0.0100 (6)	0.0127 (6)
C16	0.0438 (8)	0.0475 (9)	0.0511 (9)	−0.0062 (7)	0.0158 (7)	0.0214 (7)
C17	0.0567 (10)	0.0471 (9)	0.0470 (9)	0.0038 (7)	0.0235 (8)	0.0240 (7)
C18	0.0538 (9)	0.0330 (7)	0.0344 (7)	0.0076 (6)	0.0137 (6)	0.0132 (6)
C19	0.0425 (8)	0.0311 (7)	0.0342 (7)	−0.0015 (5)	0.0061 (6)	0.0118 (5)
C20	0.0338 (7)	0.0289 (6)	0.0335 (7)	−0.0006 (5)	0.0081 (5)	0.0117 (5)
C21	0.0774 (12)	0.0452 (9)	0.0342 (8)	0.0052 (8)	0.0107 (8)	0.0159 (7)

Geometric parameters (Å, º) top

S1—C11	1.790 (2)	C8—C13	1.5453 (18)
S1—C12	1.8191 (19)	C8—H8	0.9800
O1—C1	1.355 (2)	C9—C10	1.543 (2)
O1—C2	1.395 (2)	C9—H9	0.9800
O2—C1	1.1985 (19)	C10—C11	1.535 (2)
O3—C14	1.2270 (18)	C10—H10	0.9800
N1—C12	1.450 (2)	C11—H11A	0.9700
N1—C13	1.4851 (17)	C11—H11B	0.9700
N1—C10	1.4862 (18)	C12—H12A	0.9700
N2—C14	1.3458 (18)	C12—H12B	0.9700
N2—C15	1.4026 (19)	C13—C20	1.5058 (18)
N2—H2	0.8600	C13—C14	1.5534 (18)
C1—C9	1.512 (2)	C15—C16	1.376 (2)
C2—C7	1.384 (2)	C15—C20	1.3948 (19)
C2—C3	1.385 (2)	C16—C17	1.388 (2)
C3—C4	1.380 (3)	C16—H16	0.9300
C3—H3	0.9300	C17—C18	1.393 (2)
C4—C5	1.377 (3)	C17—H17	0.9300
C4—H4	0.9300	C18—C19	1.398 (2)
C5—C6	1.385 (2)	C18—C21	1.504 (2)
C5—H5	0.9300	C19—C20	1.385 (2)
C6—C7	1.399 (2)	C19—H19	0.9300
C6—H6	0.9300	C21—H21A	0.9600
C7—C8	1.497 (2)	C21—H21B	0.9600
C8—C9	1.5314 (18)	C21—H21C	0.9600

C11—S1—C12	85.68 (8)	C9—C10—H10	109.6
C1—O1—C2	122.33 (12)	C10—C11—S1	105.85 (11)
C12—N1—C13	118.56 (12)	C10—C11—H11A	110.6
C12—N1—C10	109.63 (12)	S1—C11—H11A	110.6
C13—N1—C10	108.19 (11)	C10—C11—H11B	110.6
C14—N2—C15	111.38 (11)	S1—C11—H11B	110.6
C14—N2—H2	124.3	H11A—C11—H11B	108.7
C15—N2—H2	124.3	N1—C12—S1	107.95 (11)
O2—C1—O1	117.29 (15)	N1—C12—H12A	110.1
O2—C1—C9	124.23 (17)	S1—C12—H12A	110.1
O1—C1—C9	118.21 (13)	N1—C12—H12B	110.1
C7—C2—C3	122.38 (16)	S1—C12—H12B	110.1
C7—C2—O1	122.58 (15)	H12A—C12—H12B	108.4
C3—C2—O1	115.03 (15)	N1—C13—C20	116.57 (11)
C4—C3—C2	118.98 (17)	N1—C13—C8	105.43 (10)
C4—C3—H3	120.5	C20—C13—C8	115.84 (11)
C2—C3—H3	120.5	N1—C13—C14	104.40 (10)
C5—C4—C3	120.40 (17)	C20—C13—C14	101.50 (11)
C5—C4—H4	119.8	C8—C13—C14	112.66 (11)
C3—C4—H4	119.8	O3—C14—N2	126.47 (13)
C4—C5—C6	119.87 (17)	O3—C14—C13	125.21 (12)
C4—C5—H5	120.1	N2—C14—C13	108.26 (12)
C6—C5—H5	120.1	C16—C15—C20	121.57 (14)
C5—C6—C7	121.20 (16)	C16—C15—N2	128.55 (14)
C5—C6—H6	119.4	C20—C15—N2	109.85 (12)
C7—C6—H6	119.4	C15—C16—C17	117.78 (15)
C2—C7—C6	117.15 (14)	C15—C16—H16	121.1
C2—C7—C8	120.27 (13)	C17—C16—H16	121.1
C6—C7—C8	122.51 (13)	C16—C17—C18	122.49 (14)
C7—C8—C9	113.73 (11)	C16—C17—H17	118.8
C7—C8—C13	116.91 (11)	C18—C17—H17	118.8
C9—C8—C13	102.92 (11)	C17—C18—C19	118.28 (14)
C7—C8—H8	107.6	C17—C18—C21	121.29 (14)
C9—C8—H8	107.6	C19—C18—C21	120.43 (15)
C13—C8—H8	107.6	C20—C19—C18	120.12 (14)
C1—C9—C8	115.20 (12)	C20—C19—H19	119.9
C1—C9—C10	111.88 (12)	C18—C19—H19	119.9
C8—C9—C10	106.10 (11)	C19—C20—C15	119.71 (13)
C1—C9—H9	107.8	C19—C20—C13	131.67 (12)
C8—C9—H9	107.8	C15—C20—C13	108.54 (12)
C10—C9—H9	107.8	C18—C21—H21A	109.5
N1—C10—C11	108.17 (13)	C18—C21—H21B	109.5
N1—C10—C9	106.68 (11)	H21A—C21—H21B	109.5
C11—C10—C9	113.15 (13)	C18—C21—H21C	109.5
N1—C10—H10	109.6	H21A—C21—H21C	109.5
C11—C10—H10	109.6	H21B—C21—H21C	109.5

C2—O1—C1—O2	−171.58 (15)	C12—N1—C13—C20	31.56 (17)
C2—O1—C1—C9	14.1 (2)	C10—N1—C13—C20	157.10 (12)
C1—O1—C2—C7	3.6 (2)	C12—N1—C13—C8	−98.51 (14)
C1—O1—C2—C3	−177.22 (15)	C10—N1—C13—C8	27.03 (14)
C7—C2—C3—C4	0.2 (3)	C12—N1—C13—C14	142.58 (13)
O1—C2—C3—C4	−179.05 (16)	C10—N1—C13—C14	−91.88 (12)
C2—C3—C4—C5	−1.0 (3)	C7—C8—C13—N1	−158.43 (11)
C3—C4—C5—C6	0.8 (3)	C9—C8—C13—N1	−33.02 (13)
C4—C5—C6—C7	0.2 (3)	C7—C8—C13—C20	71.07 (15)
C3—C2—C7—C6	0.8 (2)	C9—C8—C13—C20	−163.51 (12)
O1—C2—C7—C6	179.97 (14)	C7—C8—C13—C14	−45.18 (16)
C3—C2—C7—C8	177.75 (15)	C9—C8—C13—C14	80.23 (13)
O1—C2—C7—C8	−3.1 (2)	C15—N2—C14—O3	176.06 (14)
C5—C6—C7—C2	−1.0 (2)	C15—N2—C14—C13	−6.65 (16)
C5—C6—C7—C8	−177.86 (14)	N1—C13—C14—O3	62.34 (17)
C2—C7—C8—C9	−14.12 (18)	C20—C13—C14—O3	−176.09 (14)
C6—C7—C8—C9	162.65 (13)	C8—C13—C14—O3	−51.55 (18)
C2—C7—C8—C13	105.69 (15)	N1—C13—C14—N2	−115.00 (12)
C6—C7—C8—C13	−77.55 (17)	C20—C13—C14—N2	6.58 (14)
O2—C1—C9—C8	155.28 (16)	C8—C13—C14—N2	131.12 (12)
O1—C1—C9—C8	−30.88 (19)	C14—N2—C15—C16	−174.38 (16)
O2—C1—C9—C10	34.0 (2)	C14—N2—C15—C20	3.89 (17)
O1—C1—C9—C10	−152.16 (13)	C20—C15—C16—C17	−0.3 (2)
C7—C8—C9—C1	29.87 (17)	N2—C15—C16—C17	177.81 (15)
C13—C8—C9—C1	−97.58 (14)	C15—C16—C17—C18	−1.1 (3)
C7—C8—C9—C10	154.24 (11)	C16—C17—C18—C19	0.8 (2)
C13—C8—C9—C10	26.79 (14)	C16—C17—C18—C21	−179.81 (16)
C12—N1—C10—C11	−1.27 (17)	C17—C18—C19—C20	0.8 (2)
C13—N1—C10—C11	−131.91 (13)	C21—C18—C19—C20	−178.52 (14)
C12—N1—C10—C9	120.75 (13)	C18—C19—C20—C15	−2.2 (2)
C13—N1—C10—C9	−9.89 (14)	C18—C19—C20—C13	−178.66 (14)
C1—C9—C10—N1	115.18 (13)	C16—C15—C20—C19	1.9 (2)
C8—C9—C10—N1	−11.22 (15)	N2—C15—C20—C19	−176.49 (13)
C1—C9—C10—C11	−125.99 (15)	C16—C15—C20—C13	179.15 (14)
C8—C9—C10—C11	107.60 (14)	N2—C15—C20—C13	0.73 (16)
N1—C10—C11—S1	32.33 (15)	N1—C13—C20—C19	−74.82 (19)
C9—C10—C11—S1	−85.63 (14)	C8—C13—C20—C19	50.1 (2)
C12—S1—C11—C10	−41.61 (12)	C14—C13—C20—C19	172.50 (15)
C13—N1—C12—S1	94.75 (13)	N1—C13—C20—C15	108.41 (13)
C10—N1—C12—S1	−30.09 (15)	C8—C13—C20—C15	−126.64 (13)
C11—S1—C12—N1	42.32 (12)	C14—C13—C20—C15	−4.27 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2	0.98	2.44	2.882 (2)	107
N2—H2···O3ⁱ	0.86	2.06	2.903 (2)	168
C3—H3···O1ⁱⁱ	0.93	2.55	3.302 (2)	139
C9—H9···O2ⁱⁱⁱ	0.98	2.59	3.320 (2)	131
C21—H21C···O2^iv	0.96	2.57	3.390 (2)	144

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

Footnotes

‡Additional correspondence author, e-mail: s_selvanayagam@rediffmail.com.

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Volume 75| Part 2| February 2019| Pages 246-250

https://doi.org/10.1107/S2056989019000045

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

Crystal structures of 6a,6b,7,11a-tetra­hydro-6H,9H-spiro­[chromeno[3′,4′:3,4]pyrrolo­[1,2-c]thia­zole-11,3′-indoline]-2′,6-dione and 5′-methyl-6a,6b,7,11a-tetra­hydro-6H,9H-spiro­[chromeno[3′,4′:3,4]pyrrolo­[1,2-c]thia­zole-11,3′-indoline]-2′,6-dione

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

Footnotes

References

research communications

Crystal structures of 6a,6b,7,11a-tetrahydro-6H,9H-spiro[chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazole-11,3′-indoline]-2′,6-dione and 5′-methyl-6a,6b,7,11a-tetrahydro-6H,9H-spiro[chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazole-11,3′-indoline]-2′,6-dione

3. Supramolecular features