7-Nitro-1,2,3,4-tetra­hydro­naphthalene-1-spiro-2′-(1,3-dithiane)

Fun, H.-K.; Kia, R.; Maity, A.C.; Goswami, S.

doi:10.1107/S1600536809001536

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o347

doi:10.1107/S1600536809001536

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7-Nitro-1,2,3,4-tetrahydronaphthalene-1-spiro-2′-(1,3-dithiane)

Hoong-Kun Fun,^a ^* Reza Kia,^a Annada C. Maity ^b and Shyamaprosad Goswami ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, Bengal Engineering and Science University, Shibpur, Howrah 711 103, India
^*Correspondence e-mail: hkfun@usm.my

(Received 25 December 2008; accepted 13 January 2009; online 17 January 2009)

In the title compound, C₁₃H₁₅NO₂S₂, the nitro group is coplanar with the benzene ring to which it is attached, forming a dihedral angle of 1.07 (14)°. The dithiane ring adopts a chair conformation. In the crystal structure, molecules are linked through C—H⋯O and C—H⋯π [C⋯Cg = 3.7164 (15) Å] interactions. The crystal studied was an inversion twin with an 0.134 (5):0.866 (5) domain ratio.

Related literature

For the calculation of ring puckering parameters, see: Cremer & Pople (1975 ). For related literature including applications, see: Goswami & Maity (2008 ); Fun et al. (2009 ).

Experimental

Crystal data

C₁₃H₁₅NO₂S₂
M_r = 281.38
Orthorhombic, F d d 2
a = 12.8673 (1) Å
b = 42.2330 (6) Å
c = 9.1819 (1) Å
V = 4989.67 (10) Å³
Z = 16
Mo Kα radiation
μ = 0.42 mm⁻¹
T = 100.0 (1) K
0.41 × 0.30 × 0.06 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.849, T_max = 0.977
54206 measured reflections
6726 independent reflections
5979 reflections with I > 2σ(I)
R_int = 0.067

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.077
S = 1.06
6726 reflections
164 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983 ), 3202 Friedel pairs
Flack parameter: 0.13 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯O1ⁱ	0.97	2.58	3.4565 (18)	151
C7—H7A⋯Cg1ⁱⁱ	0.93	2.82	3.7164 (15)	162
Symmetry codes: (i) $[-x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 4}}, y+{\script{3\over 4}}, z+{\script{1\over 4}}]$ . Cg1 is the centroid of the C5–C10 benzene ring.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809001536/tk2351sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809001536/tk2351Isup2.hkl

checkCIF report

Comment top

The protection of carbonyl groups to produce dithioketals is now commonly used as an important synthetic technique in the preparation of many organic compounds, including multi-functional complex molecules (Goswami & Maity 2008; Fun et al., 2009). Herein, we report the synthesis of the title compound, (I), from 5-nitro-3,4-dihydro-2H-naphthalen-1-one using boron trifluoride etherate as the catalyst.

In (I), Fig. 1, the nitro group is co-planar with the benzene ring, forming a dihedral angle of 1.07 (14)°. The thiacyclohexane ring adopts a chair conformation with ring puckering parameters of Q = 0.7198 (11) Å, Θ = 8.49 (10)°, and Φ = 79.6 (6)° (Cremer & Pople, 1975). The crystal structure is stabilized by intermolecular C—H···π interactions (Cg1 is the centroid of the C5–C10 benzene ring), see Table 1. Further, neighbouring molecules are linked through C—H···O interactions along the c axis, Fig. 2.

Related literature top

For the calculation of ring puckering parameters, see: Cremer & Pople (1975). For related literature including applications, see: Goswami & Maity (2008); Fun et al. (2009). Cg1 is the centroid of the C5–C10 benzene ring.

Experimental top

A stirred dichloromethane (50 mL) solution of 5-nitro-3,4-dihydro-2H-naphthalen-1-one (500 mg, 2.61 mmol) and boron trifluoride etherate (0.5 mL) in was cooled to 273 K. To this 1,3-propanedithiol (450 mg, 4.1 mmol) was added dropwise over 15 min. The mixture was stirred at room temperature for 3 h and the progress of the reaction was monitored by TLC. After completion of the reaction, NaHCO₃ solution was added carefully to neutralize the mixture at room temperature. This was then extracted with dichloromethane. The organic layer was dried (anhydrous Na₂SO₄) and the solvent removed under reduced pressure. The crude product was purified by column chromatography using silica gel with 10 % ethyl acetate in petroleum ether as eluant to afford (I) (670 mg, 92 %) as a colourless crystalline solid along with other thiane derivatives.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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, 2003).

Figures top

	Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atomic numbering.
	Fig. 2. The crystal packing of (I), viewed down the a-axis showing the linking of molecules through intermolecular C—H···O interactions (dashed lines) along the c-axis.

7-Nitro-1,2,3,4-tetrahydronaphthalene-1-spiro-2'-(1,3-dithiane) top

Crystal data top

C₁₃H₁₅NO₂S₂	F(000) = 2368
M_r = 281.38	D_x = 1.498 Mg m⁻³
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 9946 reflections
a = 12.8673 (1) Å	θ = 2.8–35.0°
b = 42.2330 (6) Å	µ = 0.42 mm⁻¹
c = 9.1819 (1) Å	T = 100 K
V = 4989.67 (10) Å³	Plate, colourless
Z = 16	0.41 × 0.30 × 0.06 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6726 independent reflections
Radiation source: fine-focus sealed tube	5979 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.067
ϕ and ω scans	θ_max = 37.9°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −22→22
T_min = 0.849, T_max = 0.977	k = −72→72
54206 measured reflections	l = −15→15

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)] = 0.042	H-atom parameters constrained
wR(F²) = 0.077	w = 1/[σ²(F_o²) + (0.0258P)² + 6.6616P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
6726 reflections	Δρ_max = 0.42 e Å⁻³
164 parameters	Δρ_min = −0.23 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 3202 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.13 (5)

Crystal data top

C₁₃H₁₅NO₂S₂	V = 4989.67 (10) Å³
M_r = 281.38	Z = 16
Orthorhombic, Fdd2	Mo Kα radiation
a = 12.8673 (1) Å	µ = 0.42 mm⁻¹
b = 42.2330 (6) Å	T = 100 K
c = 9.1819 (1) Å	0.41 × 0.30 × 0.06 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6726 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	5979 reflections with I > 2σ(I)
T_min = 0.849, T_max = 0.977	R_int = 0.067
54206 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.077	Δρ_max = 0.42 e Å⁻³
S = 1.06	Δρ_min = −0.23 e Å⁻³
6726 reflections	Absolute structure: Flack (1983), 3202 Friedel pairs
164 parameters	Absolute structure parameter: 0.13 (5)
1 restraint

Special details top

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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 > 2sigma(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	0.10407 (2)	0.241432 (7)	0.34587 (3)	0.01374 (6)
S2	−0.04426 (2)	0.186537 (7)	0.31249 (4)	0.01436 (6)
O1	0.08674 (9)	0.16135 (3)	0.79752 (12)	0.0220 (2)
O2	0.22833 (9)	0.13439 (3)	0.82907 (13)	0.0258 (2)
N1	0.16994 (9)	0.15045 (3)	0.75344 (12)	0.0163 (2)
C1	0.08854 (9)	0.20066 (3)	0.27797 (13)	0.01231 (19)
C2	0.11450 (10)	0.19792 (3)	0.11508 (14)	0.0159 (2)
H2A	0.0911	0.1775	0.0791	0.019*
H2B	0.0776	0.2143	0.0618	0.019*
C3	0.23059 (10)	0.20125 (3)	0.08744 (15)	0.0167 (2)
H3A	0.2552	0.2212	0.1269	0.020*
H3B	0.2440	0.2011	−0.0165	0.020*
C4	0.28806 (11)	0.17388 (3)	0.15959 (15)	0.0167 (2)
H4A	0.2745	0.1546	0.1055	0.020*
H4B	0.3622	0.1779	0.1556	0.020*
C5	0.25624 (9)	0.16909 (3)	0.31606 (15)	0.0139 (2)
C6	0.32137 (11)	0.15154 (3)	0.40812 (16)	0.0173 (2)
H6A	0.3840	0.1439	0.3719	0.021*
C7	0.29507 (11)	0.14526 (3)	0.55123 (16)	0.0169 (2)
H7A	0.3388	0.1335	0.6112	0.020*
C8	0.20103 (10)	0.15708 (3)	0.60257 (14)	0.0140 (2)
C9	0.13528 (10)	0.17506 (3)	0.51660 (14)	0.0132 (2)
H9A	0.0739	0.1831	0.5550	0.016*
C10	0.16192 (10)	0.18097 (3)	0.37155 (13)	0.0127 (2)
C11	−0.11830 (10)	0.21555 (3)	0.20993 (15)	0.0160 (2)
H11A	−0.0973	0.2145	0.1086	0.019*
H11B	−0.1913	0.2100	0.2147	0.019*
C12	−0.10538 (11)	0.24943 (3)	0.26325 (16)	0.0176 (2)
H12A	−0.1238	0.2503	0.3656	0.021*
H12B	−0.1535	0.2629	0.2107	0.021*
C13	0.00429 (10)	0.26252 (3)	0.24439 (15)	0.0164 (2)
H13A	0.0046	0.2845	0.2747	0.020*
H13B	0.0220	0.2619	0.1418	0.020*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01297 (12)	0.01371 (11)	0.01454 (13)	0.00002 (10)	−0.00051 (10)	−0.00104 (10)
S2	0.01150 (11)	0.01563 (11)	0.01593 (13)	−0.00058 (10)	−0.00027 (10)	0.00191 (10)
O1	0.0251 (5)	0.0258 (5)	0.0152 (4)	0.0057 (4)	0.0027 (4)	−0.0002 (4)
O2	0.0277 (5)	0.0308 (5)	0.0188 (5)	0.0073 (4)	−0.0041 (4)	0.0086 (4)
N1	0.0198 (5)	0.0157 (4)	0.0135 (5)	0.0000 (4)	−0.0024 (4)	0.0006 (4)
C1	0.0110 (5)	0.0143 (4)	0.0117 (5)	−0.0003 (4)	0.0009 (4)	−0.0003 (4)
C2	0.0159 (5)	0.0197 (5)	0.0121 (5)	0.0014 (4)	0.0012 (4)	−0.0010 (4)
C3	0.0171 (5)	0.0185 (5)	0.0146 (5)	0.0009 (4)	0.0045 (4)	0.0010 (4)
C4	0.0154 (5)	0.0187 (5)	0.0159 (5)	0.0023 (4)	0.0047 (4)	0.0002 (4)
C5	0.0123 (5)	0.0135 (4)	0.0158 (5)	−0.0003 (4)	0.0018 (4)	−0.0002 (4)
C6	0.0141 (5)	0.0172 (5)	0.0205 (6)	0.0031 (4)	0.0015 (5)	0.0006 (5)
C7	0.0153 (5)	0.0156 (5)	0.0197 (6)	0.0020 (4)	−0.0024 (4)	0.0013 (4)
C8	0.0158 (5)	0.0137 (4)	0.0124 (5)	−0.0012 (4)	−0.0010 (4)	0.0003 (4)
C9	0.0123 (5)	0.0146 (5)	0.0128 (5)	−0.0001 (4)	−0.0003 (4)	−0.0006 (4)
C10	0.0116 (5)	0.0135 (4)	0.0129 (5)	−0.0009 (4)	−0.0002 (4)	−0.0002 (4)
C11	0.0129 (5)	0.0179 (5)	0.0173 (6)	0.0011 (4)	−0.0022 (4)	0.0010 (4)
C12	0.0158 (6)	0.0164 (5)	0.0207 (6)	0.0033 (4)	−0.0006 (5)	−0.0002 (4)
C13	0.0152 (5)	0.0152 (5)	0.0187 (6)	0.0019 (4)	−0.0006 (4)	0.0013 (4)

Geometric parameters (Å, º) top

S1—C13	1.8192 (13)	C5—C6	1.4022 (18)
S1—C1	1.8421 (12)	C5—C10	1.4086 (17)
S2—C11	1.8153 (13)	C6—C7	1.383 (2)
S2—C1	1.8375 (12)	C6—H6A	0.9300
O1—N1	1.2337 (16)	C7—C8	1.3915 (18)
O2—N1	1.2276 (15)	C7—H7A	0.9300
N1—C8	1.4688 (17)	C8—C9	1.3840 (17)
C1—C10	1.5236 (17)	C9—C10	1.3977 (17)
C1—C2	1.5369 (17)	C9—H9A	0.9300
C2—C3	1.5217 (18)	C11—C12	1.5216 (19)
C2—H2A	0.9700	C11—H11A	0.9700
C2—H2B	0.9700	C11—H11B	0.9700
C3—C4	1.5237 (18)	C12—C13	1.5254 (19)
C3—H3A	0.9700	C12—H12A	0.9700
C3—H3B	0.9700	C12—H12B	0.9700
C4—C5	1.5075 (19)	C13—H13A	0.9700
C4—H4A	0.9700	C13—H13B	0.9700
C4—H4B	0.9700

C13—S1—C1	101.98 (6)	C7—C6—H6A	119.1
C11—S2—C1	100.34 (6)	C5—C6—H6A	119.1
O2—N1—O1	123.49 (12)	C6—C7—C8	117.77 (12)
O2—N1—C8	118.18 (11)	C6—C7—H7A	121.1
O1—N1—C8	118.33 (11)	C8—C7—H7A	121.1
C10—C1—C2	111.90 (10)	C9—C8—C7	122.36 (12)
C10—C1—S2	107.56 (8)	C9—C8—N1	118.43 (11)
C2—C1—S2	110.21 (9)	C7—C8—N1	119.20 (11)
C10—C1—S1	104.60 (8)	C8—C9—C10	119.44 (11)
C2—C1—S1	112.11 (8)	C8—C9—H9A	120.3
S2—C1—S1	110.24 (6)	C10—C9—H9A	120.3
C3—C2—C1	111.63 (11)	C9—C10—C5	119.50 (11)
C3—C2—H2A	109.3	C9—C10—C1	118.87 (11)
C1—C2—H2A	109.3	C5—C10—C1	121.62 (11)
C3—C2—H2B	109.3	C12—C11—S2	114.24 (9)
C1—C2—H2B	109.3	C12—C11—H11A	108.7
H2A—C2—H2B	108.0	S2—C11—H11A	108.7
C2—C3—C4	109.49 (11)	C12—C11—H11B	108.7
C2—C3—H3A	109.8	S2—C11—H11B	108.7
C4—C3—H3A	109.8	H11A—C11—H11B	107.6
C2—C3—H3B	109.8	C11—C12—C13	113.91 (11)
C4—C3—H3B	109.8	C11—C12—H12A	108.8
H3A—C3—H3B	108.2	C13—C12—H12A	108.8
C5—C4—C3	112.60 (11)	C11—C12—H12B	108.8
C5—C4—H4A	109.1	C13—C12—H12B	108.8
C3—C4—H4A	109.1	H12A—C12—H12B	107.7
C5—C4—H4B	109.1	C12—C13—S1	114.67 (9)
C3—C4—H4B	109.1	C12—C13—H13A	108.6
H4A—C4—H4B	107.8	S1—C13—H13A	108.6
C6—C5—C10	119.02 (12)	C12—C13—H13B	108.6
C6—C5—C4	118.89 (11)	S1—C13—H13B	108.6
C10—C5—C4	122.07 (11)	H13A—C13—H13B	107.6
C7—C6—C5	121.88 (12)

C11—S2—C1—C10	173.57 (8)	O2—N1—C8—C7	−0.47 (18)
C11—S2—C1—C2	−64.20 (9)	O1—N1—C8—C7	179.39 (12)
C11—S2—C1—S1	60.08 (7)	C7—C8—C9—C10	1.89 (18)
C13—S1—C1—C10	−173.77 (8)	N1—C8—C9—C10	−178.31 (11)
C13—S1—C1—C2	64.78 (10)	C8—C9—C10—C5	−1.31 (17)
C13—S1—C1—S2	−58.40 (8)	C8—C9—C10—C1	179.70 (11)
C10—C1—C2—C3	−45.80 (14)	C6—C5—C10—C9	0.02 (17)
S2—C1—C2—C3	−165.44 (8)	C4—C5—C10—C9	178.31 (11)
S1—C1—C2—C3	71.36 (12)	C6—C5—C10—C1	178.98 (11)
C1—C2—C3—C4	64.05 (14)	C4—C5—C10—C1	−2.73 (18)
C2—C3—C4—C5	−49.41 (15)	C2—C1—C10—C9	−165.62 (11)
C3—C4—C5—C6	−161.70 (12)	S2—C1—C10—C9	−44.44 (13)
C3—C4—C5—C10	20.01 (17)	S1—C1—C10—C9	72.78 (12)
C10—C5—C6—C7	0.79 (19)	C2—C1—C10—C5	15.41 (16)
C4—C5—C6—C7	−177.56 (12)	S2—C1—C10—C5	136.59 (10)
C5—C6—C7—C8	−0.27 (19)	S1—C1—C10—C5	−106.18 (11)
C6—C7—C8—C9	−1.09 (19)	C1—S2—C11—C12	−61.71 (11)
C6—C7—C8—N1	179.11 (11)	S2—C11—C12—C13	65.29 (14)
O2—N1—C8—C9	179.72 (12)	C11—C12—C13—S1	−62.18 (14)
O1—N1—C8—C9	−0.42 (17)	C1—S1—C13—C12	56.76 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O1ⁱ	0.97	2.58	3.4565 (18)	151
C7—H7A···Cg1ⁱⁱ	0.93	2.82	3.7164 (15)	162

Symmetry codes: (i) −x, −y+1/2, z−1/2; (ii) −x+3/4, y+3/4, z+1/4.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₅NO₂S₂
M_r	281.38
Crystal system, space group	Orthorhombic, Fdd2
Temperature (K)	100
a, b, c (Å)	12.8673 (1), 42.2330 (6), 9.1819 (1)
V (Å³)	4989.67 (10)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.42
Crystal size (mm)	0.41 × 0.30 × 0.06

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.849, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	54206, 6726, 5979
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.864

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.077, 1.06
No. of reflections	6726
No. of parameters	164
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.23
Absolute structure	Flack (1983), 3202 Friedel pairs
Absolute structure parameter	0.13 (5)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O1ⁱ	0.97	2.58	3.4565 (18)	151
C7—H7A···Cg1ⁱⁱ	0.93	2.82	3.7164 (15)	162

Symmetry codes: (i) −x, −y+1/2, z−1/2; (ii) −x+3/4, y+3/4, z+1/4.

Acknowledgements

HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant (No. 305/PFIZIK/613312). RK thanks Universiti Sains Malaysia for a post-doctoral research fellowship. We thank the DST [SR/S1/OC-13/2005], Government of India, for financial support. ACM thanks the UGC, Government of India, for a fellowship. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant (No. 1001/PFIZIK/811012).

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