7′-(2,5-Dimeth­oxy­phen­yl)-1′,3′,5′,6′,7′,7a'-hexa­hydro­dispiro­[indan-2,5′-pyrrolo­[1,2-c][1,3]thia­zole-6′,2′′-indan]-1,3,1′′-trione

Wei, A.C.; Ali, M.A.; Choon, T.S.; Razak, I.A.; Arshad, S.

doi:10.1107/S1600536812003169

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o560-o561

doi:10.1107/S1600536812003169

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7′-(2,5-Dimethoxyphenyl)-1′,3′,5′,6′,7′,7a'-hexahydrodispiro[indan-2,5′-pyrrolo[1,2-c][1,3]thiazole-6′,2′′-indan]-1,3,1′′-trione

Ang Chee Wei,^a Mohamed Ashraf Ali,^a Tan Soo Choon,^a Ibrahim Abdul Razak ^b ^*‡ and Suhana Arshad ^b

^aInstitute for Research in Molecular Medicine, Universiti Sains Malaysia, Minden 11800, Penang, Malaysia, and ^bSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: arazaki@usm.my

(Received 16 January 2012; accepted 25 January 2012; online 4 February 2012)

In the title compound, C₃₀H₂₅NO₅S, all the five-membered rings are in envelope conformations with the spiro and methylene C atoms as the flap atoms. Intramolecular C—H⋯O interactions stabilize the molecular structure and form S(6) and S(7) ring motifs. The mean plane through the hexahydropyrrolo[1,2-c]thiazole ring [r.m.s deviation of 0.0393 (1) Å] makes dihedral angles of 60.92 (5), 88.33 (4) and 84.12 (4)° with the terminal benzene ring and the mean planes of the mono and di-oxo substituted indan rings, respectively. Molecules are linked by intermolecular C—H⋯O interactions into a three-dimensional network. In addition, C—H⋯π and π–π interactions [centroid-to-centroid distance = 3.4084 (8) Å] further stabilize the crystal structure.

Related literature

For related structures, see: Wei, Ali, Choon et al. (2011 ); Wei, Ali, Ismail et al. (2011 ); Wei, Ali, Yoon et al. (2011 ). For ring conformations, see: Cremer & Pople (1975 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₃₀H₂₅NO₅S
M_r = 511.57
Triclinic, $[P \overline 1]$
a = 9.0425 (4) Å
b = 11.1127 (5) Å
c = 13.3005 (6) Å
α = 68.016 (1)°
β = 84.588 (1)°
γ = 79.735 (1)°
V = 1218.95 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 100 K
0.36 × 0.19 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.939, T_max = 0.983
27399 measured reflections
7546 independent reflections
6172 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.106
S = 1.03
7546 reflections
336 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C16–C21 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O1	0.99	2.58	3.2234 (15)	123
C4—H4A⋯O1	1.00	2.49	3.1289 (15)	122
C22—H22B⋯O2	0.99	2.27	3.0697 (16)	137
C11—H11A⋯O3ⁱ	0.95	2.44	3.1210 (15)	129
C20—H20A⋯O2ⁱⁱ	0.95	2.48	3.1176 (14)	124
C1—H1A⋯O4ⁱⁱⁱ	0.99	2.40	3.2806 (16)	148
C30—H30C⋯O1^iv	0.98	2.47	3.2433 (18)	136
C2—H2B⋯Cg1^v	0.99	2.58	3.5224 (14)	160
Symmetry codes: (i) -x, -y+2, -z; (ii) -x, -y+1, -z+1; (iii) -x+1, -y+1, -z+1; (iv) -x+1, -y+1, -z; (v) x+1, y, z.

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812003169/rz2700sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812003169/rz2700Isup2.hkl

checkCIF report

Comment top

As part of our ongoing search for novel heterocyclic compounds with antitubercular activity (Wei, Ali, Choon et al., 2011; Wei, Ali, Ismail et al., 2011; Wei, Ali, Yoon et al., 2011) our group has synthesized the title compound as described below.

In the molecular structure (Fig. 1), all five-membered rings are in envelope conformation with puckering parameters (Cremer & Pople, 1975) Q = 0.3813 (11) Å and ϕ = 152.84 (18)° with atom C2 at the flap for the thiazolidine ring (S1/C1/N1/C3/C2), Q = 0.4536 (12) Å and ϕ = 296.92 (15)° with atom C5 at the flap for the pyrrolidine ring (N1/C3–C6), Q = 0.1467 (12) Å and ϕ = 357.9 (5)° with atom C5 at the flap for the cyclopentane ring (C5/C15/C16/C21/C22) and Q = 0.0816 (13) Å and ϕ= 1.5 (9)° with atom C6 at the flap for the cyclopentene ring (C6–C8/C13/C14). The intramolecular C2—H2A···O1, C4—H4A···O1 and C22—H22B···O2 hydrogen bonds (Table 1) stabilize the molecular structure and form S(6) and S(7) ring motifs (Bernstein et al., 1995). In addition, the mean plane through the hexahydropyrrolo[1,2-c]thiazole ring (S1/N1/C1–C6) makes dihedral angles of 60.92 (5), 88.33 (4) and 84.12 (4)° with the terminal benzene ring (C23–C28) and the mean plane of the two 2,3-dihydro-1H-indene rings (C5/C15–C22, C6–C14), respectively. The bond lengths and angles are within normal ranges and comparable to related structures (Wei, Ali, Choon et al., 2011; Wei, Ali, Ismail et al., 2011; Wei, Ali, Yoon et al., 2011).

The crystal packing is shown in Fig. 2. The molecules are linked by the intermolecular C11—H11A···O3, C20—H20A···O2, C1—H1A···O4 and C30—H30C···O1 interactions (Table 1) into three-dimensional network. In addition, the crystal structure is further stabilized by an intermolecular C2—H2B···Cg1 (Table 1) interactions (Cg1 is the centroid of the C16–C22 ring). π–π interactions are also observed with centroid to centroid distance Cg2···Cg3 = 3.4084 (8) Å [Cg2 and Cg3 are the centroids of the cyclopentane ring (C5/C15/C16/C21/C22) and cyclopentene ring (C6–C8/C13/C14), respectively].

Related literature top

For related structures, see: Wei, Ali, Choon et al. (2011); Wei, Ali, Ismail et al. (2011); Wei, Ali, Yoon et al. (2011). For ring conformations, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of 2-(2,5-dimethoxybenzylidene)-2,3-dihydro-1H-indene (0.001 mol), ninhydrin (0.001 mol) and thiazolidine-4-carboxylic acid (0.002 mol) was dissolved in methanol (10 ml) and refluxed for 4 h. After completion of the reaction as evident from TLC, the mixture was poured into crushed ice. The precipitated solid was filtered, washed and recrystallized from petroleum ether–ethyl acetate mixture (1:1 v/v) to afford the title compound as yellow crystals.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids. Intramolecular hydrogen bonds are shown as dashed lines
	Fig. 2. The crystal packing of the title compound viewed along the b axis. The H atoms not involved in intermolecular interactions (dashed lines) have been omitted for clarity.

3'-(2,5-dimethoxyphenyl)-1,1'',3,3',3'',3'a,4',6'-octahydrodispiro[indene- 2,1'-pyrrolo[1,2-c][1,3]thiazole-2',2''-indene]-1,1'',3-trione top

Crystal data top

C₃₀H₂₅NO₅S	Z = 2
M_r = 511.57	F(000) = 536
Triclinic, P1	D_x = 1.394 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0425 (4) Å	Cell parameters from 9674 reflections
b = 11.1127 (5) Å	θ = 2.3–30.7°
c = 13.3005 (6) Å	µ = 0.18 mm⁻¹
α = 68.016 (1)°	T = 100 K
β = 84.588 (1)°	Plate, yellow
γ = 79.735 (1)°	0.36 × 0.19 × 0.10 mm
V = 1218.95 (9) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	7546 independent reflections
Radiation source: fine-focus sealed tube	6172 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ϕ and ω scans	θ_max = 30.8°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
T_min = 0.939, T_max = 0.983	k = −15→16
27399 measured reflections	l = −19→19

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0547P)² + 0.3649P] where P = (F_o² + 2F_c²)/3
7546 reflections	(Δ/σ)_max = 0.001
336 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₃₀H₂₅NO₅S	γ = 79.735 (1)°
M_r = 511.57	V = 1218.95 (9) Å³
Triclinic, P1	Z = 2
a = 9.0425 (4) Å	Mo Kα radiation
b = 11.1127 (5) Å	µ = 0.18 mm⁻¹
c = 13.3005 (6) Å	T = 100 K
α = 68.016 (1)°	0.36 × 0.19 × 0.10 mm
β = 84.588 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	7546 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	6172 reflections with I > 2σ(I)
T_min = 0.939, T_max = 0.983	R_int = 0.030
27399 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.03	Δρ_max = 0.46 e Å⁻³
7546 reflections	Δρ_min = −0.34 e Å⁻³
336 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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 F² 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
S1	0.73773 (3)	0.75887 (3)	0.32247 (3)	0.02242 (8)
O1	0.48652 (10)	0.81440 (8)	0.08968 (7)	0.02018 (17)
O2	0.13926 (9)	0.78758 (9)	0.38401 (7)	0.01972 (17)
O3	0.22209 (10)	0.66773 (8)	0.08718 (6)	0.02009 (17)
O4	0.69120 (10)	0.08851 (8)	0.50375 (7)	0.02352 (18)
O5	0.42757 (10)	0.42066 (9)	0.12125 (7)	0.02060 (17)
N1	0.46129 (10)	0.70280 (9)	0.33292 (8)	0.01505 (17)
C1	0.53549 (13)	0.81258 (12)	0.32540 (10)	0.0197 (2)
H1A	0.5058	0.8389	0.3887	0.024*
H1B	0.5060	0.8890	0.2586	0.024*
C2	0.71655 (13)	0.62872 (12)	0.27699 (10)	0.0188 (2)
H2A	0.7143	0.6611	0.1969	0.023*
H2B	0.8001	0.5546	0.3019	0.023*
C3	0.56602 (12)	0.58616 (11)	0.32835 (9)	0.01487 (19)
H3A	0.5821	0.5197	0.4034	0.018*
C4	0.48564 (12)	0.53056 (11)	0.26182 (8)	0.01420 (19)
H4A	0.5193	0.5718	0.1844	0.017*
C5	0.31662 (12)	0.59219 (10)	0.27073 (8)	0.01339 (18)
C6	0.33703 (12)	0.73236 (11)	0.26064 (8)	0.01379 (19)
C7	0.36942 (12)	0.82428 (11)	0.14128 (9)	0.0156 (2)
C8	0.24279 (13)	0.93367 (11)	0.10817 (9)	0.0165 (2)
C9	0.22010 (14)	1.03660 (12)	0.00841 (10)	0.0206 (2)
H9A	0.2887	1.0420	−0.0512	0.025*
C10	0.09331 (15)	1.13115 (12)	−0.00065 (10)	0.0229 (2)
H10A	0.0747	1.2021	−0.0679	0.028*
C11	−0.00773 (14)	1.12392 (12)	0.08755 (10)	0.0233 (2)
H11A	−0.0937	1.1896	0.0789	0.028*
C12	0.01611 (13)	1.02212 (12)	0.18730 (10)	0.0208 (2)
H12A	−0.0514	1.0176	0.2474	0.025*
C13	0.14256 (13)	0.92684 (11)	0.19611 (9)	0.0167 (2)
C14	0.19522 (12)	0.81249 (11)	0.29325 (9)	0.01488 (19)
C15	0.22061 (12)	0.59216 (11)	0.18119 (8)	0.01511 (19)
C16	0.12391 (12)	0.49049 (11)	0.23166 (9)	0.01496 (19)
C17	0.03024 (13)	0.44286 (12)	0.18221 (9)	0.0189 (2)
H17A	0.0225	0.4761	0.1056	0.023*
C18	−0.05095 (13)	0.34581 (12)	0.24801 (10)	0.0209 (2)
H18A	−0.1146	0.3112	0.2164	0.025*
C19	−0.03949 (13)	0.29862 (12)	0.36080 (10)	0.0196 (2)
H19A	−0.0959	0.2322	0.4048	0.024*
C20	0.05276 (12)	0.34686 (11)	0.40993 (9)	0.0169 (2)
H20A	0.0591	0.3147	0.4866	0.020*
C21	0.13569 (12)	0.44365 (11)	0.34392 (9)	0.01400 (19)
C22	0.24062 (12)	0.51134 (11)	0.37847 (8)	0.01415 (19)
H22A	0.3162	0.4465	0.4285	0.017*
H22B	0.1843	0.5694	0.4148	0.017*
C23	0.52094 (12)	0.38279 (11)	0.29094 (9)	0.01523 (19)
C24	0.58450 (12)	0.29594 (11)	0.38738 (9)	0.0171 (2)
H24A	0.5980	0.3275	0.4426	0.020*
C25	0.62912 (12)	0.16255 (11)	0.40491 (10)	0.0183 (2)
C26	0.61226 (13)	0.11484 (12)	0.32496 (10)	0.0211 (2)
H26A	0.6467	0.0252	0.3355	0.025*
C27	0.54419 (14)	0.19992 (12)	0.22873 (10)	0.0218 (2)
H27A	0.5302	0.1675	0.1741	0.026*
C28	0.49688 (13)	0.33129 (11)	0.21227 (9)	0.0175 (2)
C29	0.75456 (15)	−0.04449 (12)	0.52243 (12)	0.0270 (3)
H29A	0.7961	−0.0853	0.5951	0.040*
H29B	0.8348	−0.0474	0.4681	0.040*
H29C	0.6764	−0.0923	0.5170	0.040*
C30	0.38015 (16)	0.37160 (14)	0.04664 (10)	0.0272 (3)
H30A	0.3236	0.4439	−0.0109	0.041*
H30B	0.3159	0.3050	0.0849	0.041*
H30C	0.4684	0.3322	0.0147	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01879 (14)	0.01845 (15)	0.03543 (17)	−0.00579 (10)	−0.00349 (11)	−0.01403 (12)
O1	0.0222 (4)	0.0175 (4)	0.0211 (4)	−0.0063 (3)	0.0074 (3)	−0.0077 (3)
O2	0.0224 (4)	0.0204 (4)	0.0179 (4)	−0.0058 (3)	0.0050 (3)	−0.0088 (3)
O3	0.0277 (4)	0.0174 (4)	0.0149 (4)	−0.0050 (3)	−0.0012 (3)	−0.0048 (3)
O4	0.0283 (4)	0.0122 (4)	0.0293 (4)	0.0013 (3)	−0.0056 (3)	−0.0076 (3)
O5	0.0279 (4)	0.0197 (4)	0.0188 (4)	−0.0060 (3)	−0.0003 (3)	−0.0112 (3)
N1	0.0163 (4)	0.0122 (4)	0.0198 (4)	−0.0047 (3)	0.0002 (3)	−0.0085 (3)
C1	0.0189 (5)	0.0160 (5)	0.0294 (6)	−0.0068 (4)	0.0015 (4)	−0.0129 (5)
C2	0.0169 (5)	0.0157 (5)	0.0271 (5)	−0.0047 (4)	−0.0001 (4)	−0.0108 (4)
C3	0.0174 (5)	0.0113 (5)	0.0178 (5)	−0.0040 (4)	−0.0007 (4)	−0.0066 (4)
C4	0.0162 (5)	0.0127 (5)	0.0159 (4)	−0.0053 (4)	0.0019 (3)	−0.0069 (4)
C5	0.0164 (4)	0.0115 (5)	0.0135 (4)	−0.0050 (4)	0.0010 (3)	−0.0051 (4)
C6	0.0155 (4)	0.0121 (5)	0.0148 (4)	−0.0040 (4)	0.0022 (3)	−0.0058 (4)
C7	0.0201 (5)	0.0118 (5)	0.0162 (5)	−0.0057 (4)	0.0028 (4)	−0.0060 (4)
C8	0.0199 (5)	0.0120 (5)	0.0183 (5)	−0.0048 (4)	0.0016 (4)	−0.0058 (4)
C9	0.0255 (6)	0.0163 (5)	0.0196 (5)	−0.0075 (4)	0.0022 (4)	−0.0048 (4)
C10	0.0290 (6)	0.0155 (5)	0.0221 (5)	−0.0043 (4)	−0.0036 (4)	−0.0033 (4)
C11	0.0256 (6)	0.0179 (6)	0.0263 (6)	0.0006 (4)	−0.0039 (5)	−0.0089 (5)
C12	0.0216 (5)	0.0193 (6)	0.0226 (5)	−0.0013 (4)	0.0006 (4)	−0.0099 (5)
C13	0.0190 (5)	0.0135 (5)	0.0188 (5)	−0.0042 (4)	0.0010 (4)	−0.0068 (4)
C14	0.0164 (5)	0.0136 (5)	0.0173 (5)	−0.0054 (4)	0.0019 (4)	−0.0078 (4)
C15	0.0178 (5)	0.0137 (5)	0.0153 (4)	−0.0030 (4)	0.0002 (4)	−0.0068 (4)
C16	0.0155 (5)	0.0143 (5)	0.0168 (5)	−0.0034 (4)	0.0000 (4)	−0.0071 (4)
C17	0.0184 (5)	0.0213 (6)	0.0205 (5)	−0.0034 (4)	−0.0018 (4)	−0.0111 (4)
C18	0.0174 (5)	0.0208 (6)	0.0299 (6)	−0.0051 (4)	−0.0015 (4)	−0.0143 (5)
C19	0.0161 (5)	0.0136 (5)	0.0294 (6)	−0.0049 (4)	0.0005 (4)	−0.0073 (4)
C20	0.0160 (5)	0.0134 (5)	0.0202 (5)	−0.0035 (4)	−0.0001 (4)	−0.0046 (4)
C21	0.0134 (4)	0.0120 (5)	0.0174 (5)	−0.0028 (4)	0.0003 (3)	−0.0061 (4)
C22	0.0170 (5)	0.0136 (5)	0.0133 (4)	−0.0062 (4)	0.0002 (3)	−0.0049 (4)
C23	0.0153 (4)	0.0134 (5)	0.0196 (5)	−0.0051 (4)	0.0031 (4)	−0.0085 (4)
C24	0.0175 (5)	0.0142 (5)	0.0222 (5)	−0.0045 (4)	0.0012 (4)	−0.0092 (4)
C25	0.0166 (5)	0.0138 (5)	0.0256 (5)	−0.0042 (4)	0.0014 (4)	−0.0081 (4)
C26	0.0206 (5)	0.0146 (5)	0.0319 (6)	−0.0050 (4)	0.0030 (4)	−0.0127 (5)
C27	0.0248 (6)	0.0196 (6)	0.0279 (6)	−0.0067 (4)	0.0030 (4)	−0.0159 (5)
C28	0.0187 (5)	0.0172 (5)	0.0201 (5)	−0.0059 (4)	0.0025 (4)	−0.0101 (4)
C29	0.0288 (6)	0.0130 (6)	0.0360 (7)	0.0018 (5)	−0.0007 (5)	−0.0077 (5)
C30	0.0384 (7)	0.0295 (7)	0.0210 (5)	−0.0110 (6)	−0.0008 (5)	−0.0149 (5)

Geometric parameters (Å, º) top

S1—C2	1.8083 (12)	C11—C12	1.3891 (17)
S1—C1	1.8213 (12)	C11—H11A	0.9500
O1—C7	1.2174 (13)	C12—C13	1.3939 (16)
O2—C14	1.2142 (13)	C12—H12A	0.9500
O3—C15	1.2180 (13)	C13—C14	1.4771 (16)
O4—C25	1.3729 (14)	C15—C16	1.4715 (15)
O4—C29	1.4229 (15)	C16—C21	1.3928 (14)
O5—C28	1.3660 (14)	C16—C17	1.3985 (15)
O5—C30	1.4264 (14)	C17—C18	1.3864 (17)
N1—C6	1.4595 (14)	C17—H17A	0.9500
N1—C1	1.4617 (14)	C18—C19	1.3990 (17)
N1—C3	1.4802 (14)	C18—H18A	0.9500
C1—H1A	0.9900	C19—C20	1.3909 (16)
C1—H1B	0.9900	C19—H19A	0.9500
C2—C3	1.5347 (16)	C20—C21	1.3951 (15)
C2—H2A	0.9900	C20—H20A	0.9500
C2—H2B	0.9900	C21—C22	1.5075 (14)
C3—C4	1.5439 (14)	C22—H22A	0.9900
C3—H3A	1.0000	C22—H22B	0.9900
C4—C23	1.5195 (15)	C23—C24	1.3862 (16)
C4—C5	1.5724 (15)	C23—C28	1.4162 (14)
C4—H4A	1.0000	C24—C25	1.4001 (16)
C5—C15	1.5387 (14)	C24—H24A	0.9500
C5—C22	1.5503 (15)	C25—C26	1.3845 (16)
C5—C6	1.5555 (15)	C26—C27	1.3951 (18)
C6—C14	1.5501 (15)	C26—H26A	0.9500
C6—C7	1.5666 (15)	C27—C28	1.3848 (16)
C7—C8	1.4768 (15)	C27—H27A	0.9500
C8—C9	1.3937 (16)	C29—H29A	0.9800
C8—C13	1.3977 (15)	C29—H29B	0.9800
C9—C10	1.3910 (17)	C29—H29C	0.9800
C9—H9A	0.9500	C30—H30A	0.9800
C10—C11	1.4039 (18)	C30—H30B	0.9800
C10—H10A	0.9500	C30—H30C	0.9800

C2—S1—C1	92.41 (5)	C8—C13—C14	110.52 (10)
C25—O4—C29	117.86 (10)	O2—C14—C13	125.67 (10)
C28—O5—C30	117.49 (10)	O2—C14—C6	125.75 (10)
C6—N1—C1	116.85 (9)	C13—C14—C6	108.55 (9)
C6—N1—C3	109.94 (8)	O3—C15—C16	127.44 (10)
C1—N1—C3	114.03 (9)	O3—C15—C5	124.96 (10)
N1—C1—S1	107.80 (8)	C16—C15—C5	107.52 (9)
N1—C1—H1A	110.1	C21—C16—C17	121.64 (10)
S1—C1—H1A	110.1	C21—C16—C15	109.33 (9)
N1—C1—H1B	110.1	C17—C16—C15	129.03 (10)
S1—C1—H1B	110.1	C18—C17—C16	118.22 (10)
H1A—C1—H1B	108.5	C18—C17—H17A	120.9
C3—C2—S1	104.63 (7)	C16—C17—H17A	120.9
C3—C2—H2A	110.8	C17—C18—C19	120.29 (10)
S1—C2—H2A	110.8	C17—C18—H18A	119.9
C3—C2—H2B	110.8	C19—C18—H18A	119.9
S1—C2—H2B	110.8	C20—C19—C18	121.43 (11)
H2A—C2—H2B	108.9	C20—C19—H19A	119.3
N1—C3—C2	108.88 (9)	C18—C19—H19A	119.3
N1—C3—C4	105.18 (8)	C19—C20—C21	118.44 (10)
C2—C3—C4	113.74 (9)	C19—C20—H20A	120.8
N1—C3—H3A	109.6	C21—C20—H20A	120.8
C2—C3—H3A	109.6	C16—C21—C20	119.98 (10)
C4—C3—H3A	109.6	C16—C21—C22	112.13 (9)
C23—C4—C3	115.74 (9)	C20—C21—C22	127.88 (10)
C23—C4—C5	117.58 (9)	C21—C22—C5	104.02 (8)
C3—C4—C5	102.55 (8)	C21—C22—H22A	111.0
C23—C4—H4A	106.7	C5—C22—H22A	111.0
C3—C4—H4A	106.7	C21—C22—H22B	111.0
C5—C4—H4A	106.7	C5—C22—H22B	111.0
C15—C5—C22	104.83 (8)	H22A—C22—H22B	109.0
C15—C5—C6	113.28 (9)	C24—C23—C28	117.81 (10)
C22—C5—C6	115.15 (8)	C24—C23—C4	123.85 (9)
C15—C5—C4	112.77 (8)	C28—C23—C4	118.21 (10)
C22—C5—C4	111.13 (8)	C23—C24—C25	121.22 (10)
C6—C5—C4	99.96 (8)	C23—C24—H24A	119.4
N1—C6—C14	112.51 (8)	C25—C24—H24A	119.4
N1—C6—C5	101.36 (8)	O4—C25—C26	124.86 (11)
C14—C6—C5	114.44 (9)	O4—C25—C24	114.81 (10)
N1—C6—C7	113.84 (9)	C26—C25—C24	120.32 (11)
C14—C6—C7	101.90 (8)	C25—C26—C27	119.25 (11)
C5—C6—C7	113.32 (8)	C25—C26—H26A	120.4
O1—C7—C8	125.97 (10)	C27—C26—H26A	120.4
O1—C7—C6	125.21 (10)	C28—C27—C26	120.45 (10)
C8—C7—C6	108.37 (9)	C28—C27—H27A	119.8
C9—C8—C13	121.07 (11)	C26—C27—H27A	119.8
C9—C8—C7	128.86 (10)	O5—C28—C27	124.19 (10)
C13—C8—C7	109.99 (10)	O5—C28—C23	114.99 (10)
C10—C9—C8	117.57 (11)	C27—C28—C23	120.81 (11)
C10—C9—H9A	121.2	O4—C29—H29A	109.5
C8—C9—H9A	121.2	O4—C29—H29B	109.5
C9—C10—C11	121.34 (11)	H29A—C29—H29B	109.5
C9—C10—H10A	119.3	O4—C29—H29C	109.5
C11—C10—H10A	119.3	H29A—C29—H29C	109.5
C12—C11—C10	120.99 (11)	H29B—C29—H29C	109.5
C12—C11—H11A	119.5	O5—C30—H30A	109.5
C10—C11—H11A	119.5	O5—C30—H30B	109.5
C11—C12—C13	117.65 (11)	H30A—C30—H30B	109.5
C11—C12—H12A	121.2	O5—C30—H30C	109.5
C13—C12—H12A	121.2	H30A—C30—H30C	109.5
C12—C13—C8	121.37 (11)	H30B—C30—H30C	109.5
C12—C13—C14	128.06 (10)

C6—N1—C1—S1	−134.10 (8)	C8—C13—C14—O2	173.06 (11)
C3—N1—C1—S1	−3.99 (11)	C12—C13—C14—C6	177.49 (11)
C2—S1—C1—N1	21.48 (9)	C8—C13—C14—C6	−5.04 (12)
C1—S1—C2—C3	−31.84 (8)	N1—C6—C14—O2	−48.10 (15)
C6—N1—C3—C2	113.37 (10)	C5—C6—C14—O2	66.90 (14)
C1—N1—C3—C2	−20.09 (12)	C7—C6—C14—O2	−170.40 (11)
C6—N1—C3—C4	−8.87 (11)	N1—C6—C14—C13	129.99 (9)
C1—N1—C3—C4	−142.33 (9)	C5—C6—C14—C13	−115.01 (10)
S1—C2—C3—N1	34.39 (10)	C7—C6—C14—C13	7.69 (11)
S1—C2—C3—C4	151.30 (8)	C22—C5—C15—O3	162.88 (11)
N1—C3—C4—C23	−149.38 (9)	C6—C5—C15—O3	36.55 (15)
C2—C3—C4—C23	91.57 (11)	C4—C5—C15—O3	−76.08 (14)
N1—C3—C4—C5	−20.04 (10)	C22—C5—C15—C16	−14.21 (11)
C2—C3—C4—C5	−139.09 (9)	C6—C5—C15—C16	−140.54 (9)
C23—C4—C5—C15	−71.71 (12)	C4—C5—C15—C16	106.83 (10)
C3—C4—C5—C15	160.10 (9)	O3—C15—C16—C21	−168.21 (11)
C23—C4—C5—C22	45.66 (12)	C5—C15—C16—C21	8.79 (12)
C3—C4—C5—C22	−82.53 (10)	O3—C15—C16—C17	11.16 (19)
C23—C4—C5—C6	167.69 (9)	C5—C15—C16—C17	−171.85 (11)
C3—C4—C5—C6	39.51 (9)	C21—C16—C17—C18	−0.56 (17)
C1—N1—C6—C14	−71.05 (12)	C15—C16—C17—C18	−179.85 (11)
C3—N1—C6—C14	156.95 (9)	C16—C17—C18—C19	0.60 (17)
C1—N1—C6—C5	166.27 (9)	C17—C18—C19—C20	−0.08 (18)
C3—N1—C6—C5	34.26 (10)	C18—C19—C20—C21	−0.51 (17)
C1—N1—C6—C7	44.24 (12)	C17—C16—C21—C20	−0.02 (16)
C3—N1—C6—C7	−87.76 (11)	C15—C16—C21—C20	179.40 (10)
C15—C5—C6—N1	−164.96 (8)	C17—C16—C21—C22	−178.82 (10)
C22—C5—C6—N1	74.39 (10)	C15—C16—C21—C22	0.60 (12)
C4—C5—C6—N1	−44.74 (9)	C19—C20—C21—C16	0.55 (16)
C15—C5—C6—C14	73.69 (11)	C19—C20—C21—C22	179.14 (10)
C22—C5—C6—C14	−46.96 (12)	C16—C21—C22—C5	−9.50 (12)
C4—C5—C6—C14	−166.09 (8)	C20—C21—C22—C5	171.82 (10)
C15—C5—C6—C7	−42.58 (12)	C15—C5—C22—C21	13.99 (11)
C22—C5—C6—C7	−163.23 (9)	C6—C5—C22—C21	139.16 (9)
C4—C5—C6—C7	77.64 (10)	C4—C5—C22—C21	−108.12 (9)
N1—C6—C7—O1	43.42 (15)	C3—C4—C23—C24	17.73 (15)
C14—C6—C7—O1	164.81 (11)	C5—C4—C23—C24	−103.87 (12)
C5—C6—C7—O1	−71.73 (14)	C3—C4—C23—C28	−157.93 (10)
N1—C6—C7—C8	−129.22 (9)	C5—C4—C23—C28	80.47 (12)
C14—C6—C7—C8	−7.83 (11)	C28—C23—C24—C25	2.52 (16)
C5—C6—C7—C8	115.62 (10)	C4—C23—C24—C25	−173.15 (10)
O1—C7—C8—C9	9.64 (19)	C29—O4—C25—C26	5.59 (17)
C6—C7—C8—C9	−177.79 (11)	C29—O4—C25—C24	−173.03 (11)
O1—C7—C8—C13	−167.21 (11)	C23—C24—C25—O4	179.56 (10)
C6—C7—C8—C13	5.37 (12)	C23—C24—C25—C26	0.87 (17)
C13—C8—C9—C10	−0.76 (17)	O4—C25—C26—C27	178.59 (11)
C7—C8—C9—C10	−177.30 (11)	C24—C25—C26—C27	−2.86 (18)
C8—C9—C10—C11	0.45 (18)	C25—C26—C27—C28	1.39 (18)
C9—C10—C11—C12	0.35 (19)	C30—O5—C28—C27	10.24 (17)
C10—C11—C12—C13	−0.82 (18)	C30—O5—C28—C23	−170.86 (10)
C11—C12—C13—C8	0.51 (17)	C26—C27—C28—O5	−179.08 (11)
C11—C12—C13—C14	177.73 (11)	C26—C27—C28—C23	2.08 (18)
C9—C8—C13—C12	0.29 (17)	C24—C23—C28—O5	177.07 (10)
C7—C8—C13—C12	177.43 (10)	C4—C23—C28—O5	−7.01 (15)
C9—C8—C13—C14	−177.38 (10)	C24—C23—C28—C27	−3.99 (16)
C7—C8—C13—C14	−0.24 (13)	C4—C23—C28—C27	171.93 (10)
C12—C13—C14—O2	−4.42 (19)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C16–C21 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1	0.99	2.58	3.2234 (15)	123
C4—H4A···O1	1.00	2.49	3.1289 (15)	122
C22—H22B···O2	0.99	2.27	3.0697 (16)	137
C11—H11A···O3ⁱ	0.95	2.44	3.1210 (15)	129
C20—H20A···O2ⁱⁱ	0.95	2.48	3.1176 (14)	124
C1—H1A···O4ⁱⁱⁱ	0.99	2.40	3.2806 (16)	148
C30—H30C···O1^iv	0.98	2.47	3.2433 (18)	136
C2—H2B···Cg1^v	0.99	2.58	3.5224 (14)	160

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

Experimental details

Crystal data
Chemical formula	C₃₀H₂₅NO₅S
M_r	511.57
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.0425 (4), 11.1127 (5), 13.3005 (6)
α, β, γ (°)	68.016 (1), 84.588 (1), 79.735 (1)
V (Å³)	1218.95 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.36 × 0.19 × 0.10

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.939, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	27399, 7546, 6172
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.721

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.106, 1.03
No. of reflections	7546
No. of parameters	336
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.34

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C16–C21 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1	0.9900	2.5800	3.2234 (15)	123.00
C4—H4A···O1	1.0000	2.4900	3.1289 (15)	122.00
C22—H22B···O2	0.9900	2.2700	3.0697 (16)	137.00
C11—H11A···O3ⁱ	0.9500	2.4400	3.1210 (15)	129.00
C20—H20A···O2ⁱⁱ	0.9500	2.4800	3.1176 (14)	124.00
C1—H1A···O4ⁱⁱⁱ	0.9900	2.4000	3.2806 (16)	148.00
C30—H30C···O1^iv	0.9800	2.4700	3.2433 (18)	136.00
C2—H2B···Cg1^v	0.9900	2.5800	3.5224 (14)	160.00

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

Footnotes

‡Thomson Reuters ResearcherID: A-5599-2009.

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia for Research University grants Nos. 1001/PFIZIK/811151 and 1001/PSK/8620012. The authors are also grateful to Pharmacogenetic and Novel Therapeutic Research, Institute for Research in Molecular Medicine, Universiti Sains Malaysia.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science 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
Wei, A. C., Ali, M. A., Choon, T. S., Quah, C. K. & Fun, H.-K. (2011). Acta Cryst. E67, o2383. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wei, A. C., Ali, M. A., Ismail, R., Quah, C. K. & Fun, H.-K. (2011). Acta Cryst. E67, o2381–o2382. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wei, A. C., Ali, M. A., Yoon, Y. K., Quah, C. K. & Fun, H.-K. (2011). Acta Cryst. E67, o2404. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 68| Part 3| March 2012| Pages o560-o561

doi:10.1107/S1600536812003169

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

7′-(2,5-Dimeth­­oxy­phen­yl)-1′,3′,5′,6′,7′,7a'-hexa­hydro­di­spiro­[indan-2,5′-pyrrolo­[1,2-c][1,3]thia­zole-6′,2′′-indan]-1,3,1′′-trione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

7′-(2,5-Dimethoxyphenyl)-1′,3′,5′,6′,7′,7a'-hexahydrodispiro[indan-2,5′-pyrrolo[1,2-c][1,3]thiazole-6′,2′′-indan]-1,3,1′′-trione