5′-Amino-1,3-dioxo-2′,3′-di­hydro-7′H-spiro­[indane-2,7′-thieno[3,2-b]pyran]-6′-carbonitrile 1′,1′-dioxide

Wang, S.-H.; Jiang, Y.-N.; Zhang, J.-N.

doi:10.1107/S1600536810010019

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o909

doi:10.1107/S1600536810010019

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5′-Amino-1,3-dioxo-2′,3′-dihydro-7′H-spiro[indane-2,7′-thieno[3,2-b]pyran]-6′-carbonitrile 1′,1′-dioxide

Shun-Hua Wang,^a ^* Yue-Ning Jiang ^b and Jiang-Na Zhang ^a

^aSchool of Mechatronic Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China, and ^bSchool of Civil Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
^*Correspondence e-mail: wangsh200912@163.com

(Received 7 March 2010; accepted 17 March 2010; online 24 March 2010)

The title compound, C₁₆H₁₀N₂O₅S, was synthesized via the condesation of dihydrothiophen-3(2H)-one 1,1-dioxide, 1H-indene-1,2,3-trione and malononitrile in ethanol. The 2,3-dihydrothiophene 1,1-dioxide and pyran rings adopt envelope conformations. The mean planes through the planar part of the pyran ring and the benzene ring are nearly perpendicular, forming a dihedral angle of 88.40 (7)°. The crystal packing is stabilized by intermolecular N—H⋯O and N—H⋯N hydrogen bonds with the sulfone O atom and the cyano N atom acting as acceptors.

Related literature

For the uses of thienopyranyl compounds such as thieno[3,2-b]pyran derivatives as antiviral agents and α-2C adrenoreceptor agonists, see: Chao et al. (2009 ); Friary et al. (1991 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₆H₁₀N₂O₅S
M_r = 342.32
Monoclinic, P 2₁ /c
a = 9.436 (3) Å
b = 10.602 (3) Å
c = 14.777 (4) Å
β = 99.137 (4)°
V = 1459.6 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 116 K
0.28 × 0.20 × 0.18 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002 ) T_min = 0.933, T_max = 0.956
9619 measured reflections
2549 independent reflections
1985 reflections with I > 2σ(I)
R_int = 0.068

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.127
S = 1.00
2549 reflections
226 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.64 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯N2ⁱ	0.89 (1)	2.23 (1)	3.067 (3)	157 (2)
N1—H1D⋯O2ⁱⁱ	0.89 (1)	2.03 (1)	2.865 (2)	156 (2)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2002); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810010019/hg2656sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810010019/hg2656Isup2.hkl

checkCIF report

Comment top

Thienopyranyl compounds, such as thieno [3,2-b]pyran derivatives, can be used as antiviral agents (Friary et al., 1991) and α-2 C adrenoreceptor agonists ( Chao et al., 2009). This led us to pay attention to the synthesis and bioactivity of these compounds. During the synthesis of thieno[3,2-b]pyran derivatives, the title compound, (I) was isolated and its structure was determined by X-ray diffraction. Here we report its crystal structure.

The molecular structure of (I) is shown in Fig. 1. In the molecular structure, the thiophene ring is in envelope conformation, for the deviation of C1 from the C2/C3/C4/S1 plane is 0.364 (3)Å with r.m.s. of 0.0056.

The pyran ring adopts an envelope conformation with atome C5 deviating from the C3/C4/C6/C7/O5 plane 0.228 (3) Å. According to Cremer & Pople analysis (Cremer & Pople, 1975), the puckering amplitude (Q) is 0.168 (2) Å. Its θ and ϕ are 103.2 (7) and 349.6 (7)°, respectively. The weighted planes of the pyran and phenyl rings are nearly perpendicular, with the dihedral angle between them 88.40 (7)°. The five membered ring of 1H-indene-1,3(2H)-dione fragment adopts an envelope conformation, for the deviation of C5 from the C9/C10/C15/C16 plane is 0.149 (3)Å with r.m.s. of 0.0033. The crystal packing is stabilized by intermolecular hydrogen bonds: N1—H1C···N2, N1—H1D···O2(Fig.2 & Table 1).

Related literature top

For the uses of thienopyranyl compounds such as thieno [3,2-b]pyran derivatives can be used as antiviral agents and α-2 C adrenoreceptor agonists, see: Chao et al. (2009); Friary et al. (1991). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

The title compound was synthesized by the reaction of dihydrothiophen-3(2H)-one-1,1-dioxide (1 mmol), 1H-indene-1,2,3-trione (1 mmol) and malononitrile (1 mmol) in 10 ml ethanol under reluxing until completion (monitored by TLC). Cooling the reaction mixture slowly gave single crystals suitable for X-ray diffraction.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2002); cell refinement: CrystalClear (Rigaku/MSC, 2002); data reduction: CrystalClear (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The packing diagram of (I). Intermolecular hydrogen bonds are shown as dashed lines.

5'-Amino-1,3-dioxo-2',3'-dihydro-7'H-spiro[indane-2,7'- thieno[3,2-b]pyran]-6'-carbonitrile 1',1'-dioxide top

Crystal data top

C₁₆H₁₀N₂O₅S	F(000) = 704
M_r = 342.32	D_x = 1.558 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5046 reflections
a = 9.436 (3) Å	θ = 1.4–27.9°
b = 10.602 (3) Å	µ = 0.25 mm⁻¹
c = 14.777 (4) Å	T = 116 K
β = 99.137 (4)°	Prism, colorless
V = 1459.6 (6) Å³	0.28 × 0.20 × 0.18 mm
Z = 4

Data collection top

Rigaku Saturn CCD area-detector diffractometer	2549 independent reflections
Radiation source: rotating anode	1985 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.068
Detector resolution: 14.63 pixels mm^-1	θ_max = 25.0°, θ_min = 2.2°
ω and ϕ scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002)	k = −12→12
T_min = 0.933, T_max = 0.956	l = −17→11
9619 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)] = 0.058	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.127	w = 1/[σ²(F_o²) + (0.0872P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
2549 reflections	Δρ_max = 0.58 e Å⁻³
226 parameters	Δρ_min = −0.64 e Å⁻³
3 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.287 (14)

Crystal data top

C₁₆H₁₀N₂O₅S	V = 1459.6 (6) Å³
M_r = 342.32	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.436 (3) Å	µ = 0.25 mm⁻¹
b = 10.602 (3) Å	T = 116 K
c = 14.777 (4) Å	0.28 × 0.20 × 0.18 mm
β = 99.137 (4)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	2549 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002)	1985 reflections with I > 2σ(I)
T_min = 0.933, T_max = 0.956	R_int = 0.068
9619 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	3 restraints
wR(F²) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.58 e Å⁻³
2549 reflections	Δρ_min = −0.64 e Å⁻³
226 parameters

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.

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	0.97876 (6)	0.43469 (5)	0.18224 (4)	0.0160 (2)
O1	0.95541 (18)	0.55710 (13)	0.14090 (11)	0.0236 (4)
O2	0.95173 (17)	0.32826 (14)	0.12109 (11)	0.0253 (4)
O3	0.68230 (16)	0.65052 (13)	0.24233 (10)	0.0205 (4)
O4	0.68085 (16)	0.20574 (13)	0.21541 (10)	0.0216 (4)
O5	0.93203 (15)	0.34731 (13)	0.42896 (10)	0.0183 (4)
N1	0.7756 (2)	0.36526 (18)	0.52595 (13)	0.0224 (5)
N2	0.4414 (2)	0.46284 (18)	0.40031 (13)	0.0242 (5)
C1	1.1509 (2)	0.42085 (19)	0.25136 (15)	0.0170 (5)
H1A	1.2145	0.3705	0.2204	0.020*
H1B	1.1936	0.5034	0.2644	0.020*
C2	1.1251 (2)	0.35644 (19)	0.33972 (15)	0.0172 (5)
H2A	1.1471	0.2672	0.3379	0.021*
H2B	1.1854	0.3937	0.3922	0.021*
C3	0.9718 (2)	0.37524 (18)	0.34620 (14)	0.0151 (5)
C4	0.8818 (2)	0.41635 (18)	0.27348 (14)	0.0148 (5)
C5	0.7227 (2)	0.42359 (18)	0.26815 (15)	0.0149 (5)
C6	0.6933 (2)	0.41396 (18)	0.36651 (15)	0.0150 (5)
C7	0.7939 (2)	0.37715 (18)	0.43869 (14)	0.0160 (5)
C8	0.5539 (2)	0.43993 (18)	0.38449 (15)	0.0160 (5)
C9	0.6480 (2)	0.54337 (19)	0.22236 (15)	0.0158 (5)
C10	0.5243 (2)	0.50111 (19)	0.15446 (14)	0.0151 (5)
C11	0.4185 (2)	0.5739 (2)	0.10321 (15)	0.0201 (5)
H11	0.4207	0.6615	0.1074	0.024*
C12	0.3101 (2)	0.5133 (2)	0.04602 (15)	0.0233 (6)
H12	0.2375	0.5604	0.0118	0.028*
C13	0.3079 (3)	0.3814 (2)	0.03878 (15)	0.0226 (5)
H13	0.2340	0.3425	−0.0005	0.027*
C14	0.4129 (2)	0.3084 (2)	0.08852 (14)	0.0197 (5)
H14	0.4117	0.2210	0.0831	0.024*
C15	0.5215 (2)	0.36997 (18)	0.14740 (14)	0.0152 (5)
C16	0.6443 (2)	0.31490 (19)	0.20917 (14)	0.0156 (5)
H1C	0.6992 (18)	0.394 (2)	0.5484 (15)	0.036 (7)*
H1D	0.841 (2)	0.325 (2)	0.5651 (14)	0.047 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0134 (4)	0.0201 (4)	0.0148 (3)	−0.0004 (2)	0.0034 (2)	−0.0006 (2)
O1	0.0225 (10)	0.0262 (9)	0.0231 (9)	0.0053 (6)	0.0064 (7)	0.0088 (7)
O2	0.0227 (10)	0.0316 (9)	0.0226 (9)	−0.0070 (7)	0.0062 (7)	−0.0101 (7)
O3	0.0213 (10)	0.0148 (8)	0.0257 (9)	−0.0017 (6)	0.0046 (7)	−0.0003 (7)
O4	0.0219 (9)	0.0154 (8)	0.0268 (9)	0.0029 (6)	0.0016 (7)	0.0006 (7)
O5	0.0147 (9)	0.0241 (8)	0.0167 (8)	0.0048 (6)	0.0043 (6)	0.0037 (6)
N1	0.0222 (12)	0.0287 (11)	0.0171 (10)	0.0084 (9)	0.0056 (9)	0.0052 (9)
N2	0.0179 (12)	0.0353 (11)	0.0196 (11)	0.0024 (8)	0.0039 (9)	−0.0013 (8)
C1	0.0133 (12)	0.0185 (11)	0.0191 (12)	−0.0018 (9)	0.0029 (9)	−0.0009 (9)
C2	0.0152 (12)	0.0183 (10)	0.0181 (11)	0.0014 (9)	0.0025 (9)	0.0007 (9)
C3	0.0175 (12)	0.0131 (10)	0.0157 (11)	0.0008 (8)	0.0051 (9)	−0.0015 (9)
C4	0.0135 (12)	0.0162 (10)	0.0156 (11)	−0.0006 (8)	0.0053 (9)	−0.0018 (9)
C5	0.0124 (12)	0.0157 (10)	0.0167 (11)	−0.0001 (8)	0.0027 (9)	0.0002 (9)
C6	0.0141 (12)	0.0150 (10)	0.0167 (11)	0.0009 (8)	0.0047 (9)	0.0005 (9)
C7	0.0168 (12)	0.0127 (10)	0.0196 (12)	0.0011 (8)	0.0065 (9)	−0.0003 (9)
C8	0.0185 (13)	0.0163 (11)	0.0125 (11)	−0.0024 (9)	0.0005 (9)	0.0002 (8)
C9	0.0140 (12)	0.0193 (11)	0.0158 (11)	0.0014 (8)	0.0074 (9)	0.0002 (9)
C10	0.0139 (12)	0.0187 (11)	0.0136 (11)	0.0013 (9)	0.0050 (9)	0.0010 (9)
C11	0.0217 (13)	0.0201 (11)	0.0192 (12)	0.0054 (9)	0.0052 (10)	0.0012 (9)
C12	0.0215 (14)	0.0305 (12)	0.0168 (12)	0.0077 (10)	−0.0007 (10)	0.0042 (10)
C13	0.0189 (13)	0.0309 (12)	0.0169 (12)	−0.0023 (10)	−0.0008 (10)	−0.0034 (10)
C14	0.0214 (13)	0.0205 (11)	0.0175 (12)	−0.0008 (9)	0.0040 (10)	−0.0001 (9)
C15	0.0138 (12)	0.0187 (10)	0.0135 (11)	−0.0001 (8)	0.0038 (9)	−0.0001 (9)
C16	0.0143 (12)	0.0179 (11)	0.0158 (11)	−0.0012 (9)	0.0064 (9)	0.0017 (9)

Geometric parameters (Å, º) top

S1—O1	1.4364 (15)	C4—C5	1.493 (3)
S1—O2	1.4428 (16)	C5—C6	1.526 (3)
S1—C4	1.756 (2)	C5—C9	1.554 (3)
S1—C1	1.782 (2)	C5—C16	1.559 (3)
O3—C9	1.205 (2)	C6—C7	1.368 (3)
O4—C16	1.207 (2)	C6—C8	1.409 (3)
O5—C3	1.367 (2)	C9—C10	1.482 (3)
O5—C7	1.371 (3)	C10—C11	1.388 (3)
N1—C7	1.334 (3)	C10—C15	1.394 (3)
N1—H1C	0.893 (9)	C11—C12	1.378 (3)
N1—H1D	0.889 (9)	C11—H11	0.9300
N2—C8	1.149 (3)	C12—C13	1.403 (3)
C1—C2	1.527 (3)	C12—H12	0.9300
C1—H1A	0.9700	C13—C14	1.374 (3)
C1—H1B	0.9700	C13—H13	0.9300
C2—C3	1.478 (3)	C14—C15	1.396 (3)
C2—H2A	0.9700	C14—H14	0.9300
C2—H2B	0.9700	C15—C16	1.477 (3)
C3—C4	1.333 (3)

O1—S1—O2	116.12 (10)	C9—C5—C16	102.61 (17)
O1—S1—C4	111.29 (10)	C7—C6—C8	117.51 (19)
O2—S1—C4	109.41 (9)	C7—C6—C5	123.58 (19)
O1—S1—C1	112.48 (10)	C8—C6—C5	118.87 (19)
O2—S1—C1	110.42 (10)	N1—C7—C6	126.9 (2)
C4—S1—C1	95.13 (10)	N1—C7—O5	110.57 (19)
C3—O5—C7	116.39 (16)	C6—C7—O5	122.56 (18)
C7—N1—H1C	124.3 (15)	N2—C8—C6	178.7 (2)
C7—N1—H1D	119.4 (16)	O3—C9—C10	127.1 (2)
H1C—N1—H1D	116.3 (15)	O3—C9—C5	125.3 (2)
C2—C1—S1	105.81 (14)	C10—C9—C5	107.55 (16)
C2—C1—H1A	110.6	C11—C10—C15	120.68 (19)
S1—C1—H1A	110.6	C11—C10—C9	128.46 (19)
C2—C1—H1B	110.6	C15—C10—C9	110.84 (17)
S1—C1—H1B	110.6	C12—C11—C10	118.3 (2)
H1A—C1—H1B	108.7	C12—C11—H11	120.8
C3—C2—C1	106.59 (17)	C10—C11—H11	120.8
C3—C2—H2A	110.4	C11—C12—C13	120.8 (2)
C1—C2—H2A	110.4	C11—C12—H12	119.6
C3—C2—H2B	110.4	C13—C12—H12	119.6
C1—C2—H2B	110.4	C14—C13—C12	121.3 (2)
H2A—C2—H2B	108.6	C14—C13—H13	119.3
C4—C3—O5	124.2 (2)	C12—C13—H13	119.3
C4—C3—C2	119.78 (19)	C13—C14—C15	117.7 (2)
O5—C3—C2	116.05 (18)	C13—C14—H14	121.1
C3—C4—C5	124.48 (19)	C15—C14—H14	121.1
C3—C4—S1	108.20 (16)	C10—C15—C14	121.09 (19)
C5—C4—S1	126.58 (16)	C10—C15—C16	110.13 (17)
C4—C5—C6	106.25 (17)	C14—C15—C16	128.78 (19)
C4—C5—C9	116.60 (17)	O4—C16—C15	127.8 (2)
C6—C5—C9	109.32 (16)	O4—C16—C5	124.15 (19)
C4—C5—C16	112.07 (16)	C15—C16—C5	108.03 (16)
C6—C5—C16	109.94 (16)

O1—S1—C1—C2	135.04 (14)	C3—O5—C7—C6	10.1 (3)
O2—S1—C1—C2	−93.46 (15)	C7—C6—C8—N2	59 (11)
C4—S1—C1—C2	19.47 (15)	C5—C6—C8—N2	−123 (11)
S1—C1—C2—C3	−20.47 (19)	C4—C5—C9—O3	−51.7 (3)
C7—O5—C3—C4	−7.2 (3)	C6—C5—C9—O3	68.8 (3)
C7—O5—C3—C2	173.23 (16)	C16—C5—C9—O3	−174.58 (19)
C1—C2—C3—C4	13.2 (3)	C4—C5—C9—C10	131.25 (19)
C1—C2—C3—O5	−167.28 (16)	C6—C5—C9—C10	−108.26 (18)
O5—C3—C4—C5	−7.5 (3)	C16—C5—C9—C10	8.4 (2)
C2—C3—C4—C5	172.05 (18)	O3—C9—C10—C11	−3.5 (4)
O5—C3—C4—S1	−178.14 (15)	C5—C9—C10—C11	173.4 (2)
C2—C3—C4—S1	1.4 (2)	O3—C9—C10—C15	177.91 (19)
O1—S1—C4—C3	−129.26 (15)	C5—C9—C10—C15	−5.1 (2)
O2—S1—C4—C3	101.07 (16)	C15—C10—C11—C12	0.6 (3)
C1—S1—C4—C3	−12.70 (16)	C9—C10—C11—C12	−177.8 (2)
O1—S1—C4—C5	60.3 (2)	C10—C11—C12—C13	−0.9 (3)
O2—S1—C4—C5	−69.34 (19)	C11—C12—C13—C14	0.3 (3)
C1—S1—C4—C5	176.89 (18)	C12—C13—C14—C15	0.6 (3)
C3—C4—C5—C6	16.4 (3)	C11—C10—C15—C14	0.3 (3)
S1—C4—C5—C6	−174.71 (14)	C9—C10—C15—C14	178.97 (19)
C3—C4—C5—C9	138.5 (2)	C11—C10—C15—C16	−179.47 (19)
S1—C4—C5—C9	−52.6 (2)	C9—C10—C15—C16	−0.8 (2)
C3—C4—C5—C16	−103.7 (2)	C13—C14—C15—C10	−0.9 (3)
S1—C4—C5—C16	65.2 (2)	C13—C14—C15—C16	178.8 (2)
C4—C5—C6—C7	−13.2 (3)	C10—C15—C16—O4	−173.9 (2)
C9—C5—C6—C7	−139.8 (2)	C14—C15—C16—O4	6.3 (4)
C16—C5—C6—C7	108.3 (2)	C10—C15—C16—C5	6.4 (2)
C4—C5—C6—C8	169.09 (17)	C14—C15—C16—C5	−173.4 (2)
C9—C5—C6—C8	42.5 (2)	C4—C5—C16—O4	45.5 (3)
C16—C5—C6—C8	−69.4 (2)	C6—C5—C16—O4	−72.4 (2)
C8—C6—C7—N1	−1.5 (3)	C9—C5—C16—O4	171.39 (18)
C5—C6—C7—N1	−179.2 (2)	C4—C5—C16—C15	−134.76 (18)
C8—C6—C7—O5	178.80 (17)	C6—C5—C16—C15	107.32 (18)
C5—C6—C7—O5	1.0 (3)	C9—C5—C16—C15	−8.9 (2)
C3—O5—C7—N1	−169.63 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···N2ⁱ	0.89 (1)	2.23 (1)	3.067 (3)	157 (2)
N1—H1D···O2ⁱⁱ	0.89 (1)	2.03 (1)	2.865 (2)	156 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₀N₂O₅S
M_r	342.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	116
a, b, c (Å)	9.436 (3), 10.602 (3), 14.777 (4)
β (°)	99.137 (4)
V (Å³)	1459.6 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.28 × 0.20 × 0.18

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2002)
T_min, T_max	0.933, 0.956
No. of measured, independent and observed [I > 2σ(I)] reflections	9619, 2549, 1985
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.127, 1.00
No. of reflections	2549
No. of parameters	226
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.64

Computer programs: CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···N2ⁱ	0.893 (9)	2.227 (13)	3.067 (3)	157 (2)
N1—H1D···O2ⁱⁱ	0.889 (9)	2.031 (14)	2.865 (2)	156 (2)

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

Acknowledgements

The authors acknowledge the financial support of the Natural Science Foundation of Gansu Province (No. 0916RJZA0500).

References

Chao, J. H., Zheng, J. Y. & Aslanian, R. G. (2009). WO Patent No. 2009020578. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Friary, R. J., Schwerdt, J. H. & Ganguly, A. K. (1991). US Patent No. 5 034 531. Google Scholar
Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 66| Part 4| April 2010| Page o909

doi:10.1107/S1600536810010019

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

5′-Amino-1,3-dioxo-2′,3′-di­hydro-7′H-spiro­[indane-2,7′-thieno[3,2-b]pyran]-6′-carbo­nitrile 1′,1′-dioxide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

5′-Amino-1,3-dioxo-2′,3′-dihydro-7′H-spiro[indane-2,7′-thieno[3,2-b]pyran]-6′-carbonitrile 1′,1′-dioxide