(3-Oxo-3H-benzo[f]chromen-1-yl)methyl piperidine-1-carbodithio­ate

Kotresh, O.; Kumar, K.M.; Mahabaleshwaraiah, N.M.; Arunkashi, H.K.; Devarajegowda, H.C.

doi:10.1107/S1600536812042870

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3167

doi:10.1107/S1600536812042870

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(3-Oxo-3H-benzo[f]chromen-1-yl)methyl piperidine-1-carbodithioate

O. Kotresh,^a K. Mahesh Kumar,^a N. M. Mahabaleshwaraiah,^a H. K. Arunkashi ^b and H. C. Devarajegowda ^b ^*

^aDepartment of Chemistry, Karnatak University's Karnatak Science College, Dharwad, Karnataka 580 001, India, and ^bDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India
^*Correspondence e-mail: devarajegowda@yahoo.com

(Received 11 October 2012; accepted 13 October 2012; online 20 October 2012)

In the title compound, C₂₀H₁₉N O₂S₂,the 3Hbenzo-chromene ring system is nearly planar, with a maximum deviation of 0.036 (2) Å, and the piperidine ring adopts a chair conformation: the bond-angle sum for its N atom is 358.7°. The dihedral angle between the 3H-benzo[f]chromene ring and the piperidine ring is 89.07 (8)°. In the crystal, C—H⋯O hydrogen bonds lead to [010] C(6) chains and weak aromatic π–π interactions between the fused pyran ring and fused benzene ring of benzochromene [centroid–centroid distance = 3.652 (1) Å] are also observed.

Related literature

For a related structure, background to coumarins and details of the synthesis of the title compound, see: Kumar et al. (2012 ).

Experimental

Crystal data

C₂₀H₁₉NO₂S₂
M_r = 369.48
Monoclinic, P 2₁ /c
a = 12.4508 (3) Å
b = 10.1924 (3) Å
c = 14.0188 (4) Å
β = 100.953 (2)°
V = 1746.63 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 296 K
0.24 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.770, T_max = 1.000
12000 measured reflections
2993 independent reflections
2380 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.082
S = 1.06
2993 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O4ⁱ	0.93	2.56	3.308 (2)	138
Symmetry code: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812042870/hb6973sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812042870/hb6973Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812042870/hb6973Isup3.cml

checkCIF report

Comment top

As part of our ongoing studies of coumarins (or 2H-chromen-2-ones) with possible biological activities (Kumar et al., 2012), we now describe the structure of the title compound, (I).

The asymmetric unit of (I) is shown in Fig. 1. The 3Hbenzo- chromene ring system (O3/C6–C18) is essentially planar, with a maximum deviation of 0.036 (2) Å for atom C15 and the piperidine ring adopts a chair conformation. The dihedral angle between the 3Hbenzo- chromene (O3/C6–C18) ring and the piperidine (N5/C21–C25) ring is 81.07 (8)°.

In the crystal structure, (Fig. 2), C11—H11···O4 hydrogen bonds and π–π interactions between the fused pyran ring (O3/C6–C10) and fused benzene(C13–C18) ring of benzo-chromene [shortest centroid–centroid distance = 3.652 (1) Å] are observed.

Related literature top

For a related structure, background to coumarins and details of the synthesis of the title compound, see: Kumar et al. (2012).

Experimental top

This compound was prepared according to the reported method (Kumar et al., 2012). Colourless needles of the title compound were grown from a mixed solution of EtOH / CHCl₃(V/V = 1/1) by slow evaporation at room temperature. Yield= 85%, m.p. 455 K.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary radius.

(3-Oxo-3H-benzo[f]chromen-1-yl)methyl piperidine-1-carbodithioate top

Crystal data top

C₂₀H₁₉NO₂S₂	F(000) = 776
M_r = 369.48	D_x = 1.405 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 455 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.4508 (3) Å	Cell parameters from 2993 reflections
b = 10.1924 (3) Å	θ = 1.7–24.9°
c = 14.0188 (4) Å	µ = 0.32 mm⁻¹
β = 100.953 (2)°	T = 296 K
V = 1746.63 (8) Å³	Plate, colourless
Z = 4	0.24 × 0.20 × 0.12 mm

Data collection top

Bruker SMART CCD diffractometer	2993 independent reflections
Radiation source: fine-focus sealed tube	2380 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ω and ϕ scans	θ_max = 24.9°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −14→14
T_min = 0.770, T_max = 1.000	k = −12→10
12000 measured reflections	l = −16→16

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.082	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0374P)² + 0.1604P] where P = (F_o² + 2F_c²)/3
2993 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₂₀H₁₉NO₂S₂	V = 1746.63 (8) Å³
M_r = 369.48	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.4508 (3) Å	µ = 0.32 mm⁻¹
b = 10.1924 (3) Å	T = 296 K
c = 14.0188 (4) Å	0.24 × 0.20 × 0.12 mm
β = 100.953 (2)°

Data collection top

Bruker SMART CCD diffractometer	2993 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	2380 reflections with I > 2σ(I)
T_min = 0.770, T_max = 1.000	R_int = 0.029
12000 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.082	H-atom parameters constrained
S = 1.06	Δρ_max = 0.16 e Å⁻³
2993 reflections	Δρ_min = −0.14 e Å⁻³
226 parameters

Special details top

Experimental. IR (KBr): 655 cm^-1(C—S), 1235 cm^-1(C=S), 1007 cm^-1(C—O), 877 cm^-1(C—N),1137 cm^-1(C—O—C), 1720 cm^-1(C=O). GCMS: m/e: 369. 1H NMR (400 MHz, CDCl₃, \?, p.p.m.): 1.74(s, 6H, Piperidine-CH₂), 3.90(s, 2H, Piperidine-CH₂), 4.32(s, 2H Piperidine-CH₂), 4.85(s, 2H, Methylene-CH₂), 6.67(s,1H, Ar—H), 7.64(s, 2H, Ar—H), 7.65(s, 2H, Ar—H), 7.88(m,1H, Ar—H), 8.56(m,1H, Ar—H). Elemental analysis for C₂₀H₁₉NO₂S₂: C, 64.93; H, 5.11; N, 3.68.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.27800 (4)	0.69065 (5)	0.37375 (3)	0.05055 (15)
S2	0.48792 (4)	0.78586 (6)	0.49758 (3)	0.06250 (17)
O3	0.09397 (10)	0.81457 (13)	0.67448 (8)	0.0520 (3)
O4	0.12823 (11)	0.60307 (14)	0.68426 (9)	0.0669 (4)
N5	0.46698 (11)	0.57768 (15)	0.38149 (9)	0.0502 (4)
C6	0.13705 (14)	0.7038 (2)	0.64137 (12)	0.0502 (5)
C7	0.18621 (14)	0.72190 (18)	0.55883 (12)	0.0469 (4)
H7	0.2160	0.6487	0.5340	0.056*
C8	0.19268 (12)	0.83761 (17)	0.51406 (11)	0.0412 (4)
C9	0.15023 (12)	0.95573 (17)	0.55367 (11)	0.0410 (4)
C10	0.10299 (13)	0.93577 (18)	0.63419 (11)	0.0448 (4)
C11	0.05735 (16)	1.0358 (2)	0.68248 (13)	0.0619 (6)
H11	0.0263	1.0168	0.7362	0.074*
C12	0.05917 (17)	1.1592 (2)	0.64997 (15)	0.0691 (6)
H12	0.0297	1.2258	0.6824	0.083*
C13	0.10462 (15)	1.19123 (19)	0.56782 (14)	0.0574 (5)
C14	0.10225 (19)	1.3216 (2)	0.53383 (19)	0.0753 (7)
H14	0.0715	1.3865	0.5668	0.090*
C15	0.14331 (19)	1.3548 (2)	0.4550 (2)	0.0779 (7)
H15	0.1404	1.4412	0.4333	0.093*
C16	0.18980 (18)	1.2583 (2)	0.40712 (19)	0.0778 (7)
H16	0.2185	1.2806	0.3527	0.093*
C17	0.19479 (16)	1.1313 (2)	0.43759 (16)	0.0662 (6)
H17	0.2279	1.0695	0.4039	0.079*
C18	0.15154 (12)	1.09039 (18)	0.51844 (12)	0.0473 (4)
C19	0.24178 (14)	0.84276 (18)	0.42314 (12)	0.0491 (4)
H19A	0.3070	0.8968	0.4371	0.059*
H19B	0.1901	0.8873	0.3731	0.059*
C20	0.42141 (14)	0.67877 (17)	0.41861 (11)	0.0438 (4)
C21	0.41030 (16)	0.48928 (19)	0.30567 (13)	0.0568 (5)
H21A	0.3318	0.5002	0.2989	0.068*
H21B	0.4282	0.3990	0.3239	0.068*
C22	0.44414 (17)	0.5192 (2)	0.21075 (13)	0.0663 (6)
H22A	0.4193	0.6065	0.1894	0.080*
H22B	0.4098	0.4571	0.1619	0.080*
C23	0.56693 (18)	0.5117 (2)	0.22032 (15)	0.0780 (7)
H23A	0.5871	0.5421	0.1606	0.094*
H23B	0.5903	0.4211	0.2303	0.094*
C24	0.62477 (16)	0.5941 (2)	0.30422 (15)	0.0700 (6)
H24A	0.7030	0.5792	0.3131	0.084*
H24B	0.6112	0.6862	0.2892	0.084*
C25	0.58614 (14)	0.5613 (2)	0.39697 (13)	0.0630 (6)
H25A	0.6055	0.4715	0.4158	0.076*
H25B	0.6212	0.6189	0.4488	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0437 (3)	0.0616 (3)	0.0487 (3)	0.0059 (2)	0.01482 (19)	−0.0062 (2)
S2	0.0606 (3)	0.0702 (4)	0.0536 (3)	0.0040 (3)	0.0032 (2)	−0.0135 (2)
O3	0.0525 (7)	0.0653 (9)	0.0419 (6)	0.0039 (6)	0.0182 (5)	0.0000 (6)
O4	0.0801 (9)	0.0660 (10)	0.0613 (8)	0.0012 (8)	0.0303 (7)	0.0170 (8)
N5	0.0491 (8)	0.0593 (10)	0.0437 (7)	0.0116 (7)	0.0126 (6)	−0.0042 (7)
C6	0.0484 (10)	0.0607 (14)	0.0433 (9)	0.0027 (9)	0.0130 (8)	0.0041 (9)
C7	0.0466 (10)	0.0502 (12)	0.0478 (9)	0.0071 (8)	0.0192 (8)	0.0002 (8)
C8	0.0324 (8)	0.0510 (12)	0.0416 (8)	0.0034 (8)	0.0108 (7)	0.0005 (8)
C9	0.0302 (8)	0.0487 (11)	0.0440 (9)	0.0018 (7)	0.0069 (7)	−0.0048 (8)
C10	0.0384 (9)	0.0544 (12)	0.0411 (9)	0.0026 (8)	0.0062 (7)	−0.0051 (8)
C11	0.0632 (13)	0.0766 (17)	0.0473 (10)	0.0106 (11)	0.0143 (9)	−0.0165 (10)
C12	0.0717 (14)	0.0691 (17)	0.0649 (13)	0.0160 (12)	0.0090 (11)	−0.0274 (12)
C13	0.0477 (11)	0.0527 (13)	0.0657 (12)	0.0018 (9)	−0.0043 (9)	−0.0156 (10)
C14	0.0724 (15)	0.0483 (14)	0.0958 (17)	0.0052 (11)	−0.0076 (13)	−0.0186 (12)
C15	0.0727 (15)	0.0456 (14)	0.1077 (18)	−0.0077 (11)	−0.0022 (13)	0.0075 (13)
C16	0.0667 (14)	0.0626 (16)	0.1065 (17)	−0.0027 (12)	0.0223 (13)	0.0195 (13)
C17	0.0600 (12)	0.0517 (14)	0.0930 (15)	0.0079 (10)	0.0298 (11)	0.0149 (11)
C18	0.0316 (9)	0.0487 (12)	0.0594 (10)	−0.0001 (8)	0.0033 (7)	−0.0035 (9)
C19	0.0467 (10)	0.0546 (12)	0.0507 (9)	0.0123 (8)	0.0209 (8)	0.0073 (8)
C20	0.0484 (10)	0.0524 (12)	0.0334 (8)	0.0075 (8)	0.0151 (7)	0.0053 (7)
C21	0.0619 (12)	0.0504 (12)	0.0602 (11)	0.0073 (9)	0.0172 (9)	−0.0064 (9)
C22	0.0743 (14)	0.0786 (16)	0.0473 (10)	0.0168 (11)	0.0150 (9)	−0.0072 (10)
C23	0.0788 (15)	0.106 (2)	0.0560 (12)	0.0296 (13)	0.0302 (11)	0.0052 (12)
C24	0.0554 (12)	0.0809 (17)	0.0787 (14)	0.0189 (11)	0.0252 (10)	0.0102 (12)
C25	0.0504 (11)	0.0821 (16)	0.0569 (11)	0.0239 (10)	0.0112 (9)	−0.0007 (10)

Geometric parameters (Å, º) top

S1—C20	1.7809 (17)	C14—H14	0.9300
S1—C19	1.7904 (18)	C15—C16	1.379 (3)
S2—C20	1.6597 (18)	C15—H15	0.9300
O3—C6	1.368 (2)	C16—C17	1.361 (3)
O3—C10	1.372 (2)	C16—H16	0.9300
O4—C6	1.205 (2)	C17—C18	1.407 (3)
N5—C20	1.329 (2)	C17—H17	0.9300
N5—C25	1.468 (2)	C19—H19A	0.9700
N5—C21	1.468 (2)	C19—H19B	0.9700
C6—C7	1.420 (2)	C21—C22	1.501 (3)
C7—C8	1.346 (2)	C21—H21A	0.9700
C7—H7	0.9300	C21—H21B	0.9700
C8—C9	1.466 (2)	C22—C23	1.511 (3)
C8—C19	1.516 (2)	C22—H22A	0.9700
C9—C10	1.383 (2)	C22—H22B	0.9700
C9—C18	1.460 (2)	C23—C24	1.512 (3)
C10—C11	1.403 (2)	C23—H23A	0.9700
C11—C12	1.339 (3)	C23—H23B	0.9700
C11—H11	0.9300	C24—C25	1.507 (3)
C12—C13	1.414 (3)	C24—H24A	0.9700
C12—H12	0.9300	C24—H24B	0.9700
C13—C14	1.410 (3)	C25—H25A	0.9700
C13—C18	1.425 (2)	C25—H25B	0.9700
C14—C15	1.346 (3)

C20—S1—C19	103.40 (8)	C17—C18—C9	125.56 (17)
C6—O3—C10	122.36 (13)	C13—C18—C9	118.80 (16)
C20—N5—C25	121.67 (16)	C8—C19—S1	117.83 (12)
C20—N5—C21	125.25 (15)	C8—C19—H19A	107.8
C25—N5—C21	111.76 (14)	S1—C19—H19A	107.8
O4—C6—O3	117.06 (16)	C8—C19—H19B	107.8
O4—C6—C7	127.68 (18)	S1—C19—H19B	107.8
O3—C6—C7	115.26 (16)	H19A—C19—H19B	107.2
C8—C7—C6	124.55 (16)	N5—C20—S2	125.10 (13)
C8—C7—H7	117.7	N5—C20—S1	112.86 (13)
C6—C7—H7	117.7	S2—C20—S1	122.04 (10)
C7—C8—C9	119.04 (14)	N5—C21—C22	109.86 (16)
C7—C8—C19	119.48 (15)	N5—C21—H21A	109.7
C9—C8—C19	121.48 (14)	C22—C21—H21A	109.7
C10—C9—C18	116.62 (15)	N5—C21—H21B	109.7
C10—C9—C8	115.34 (15)	C22—C21—H21B	109.7
C18—C9—C8	128.03 (14)	H21A—C21—H21B	108.2
O3—C10—C9	123.31 (15)	C21—C22—C23	111.14 (16)
O3—C10—C11	112.56 (15)	C21—C22—H22A	109.4
C9—C10—C11	124.12 (18)	C23—C22—H22A	109.4
C12—C11—C10	118.93 (19)	C21—C22—H22B	109.4
C12—C11—H11	120.5	C23—C22—H22B	109.4
C10—C11—H11	120.5	H22A—C22—H22B	108.0
C11—C12—C13	121.94 (18)	C22—C23—C24	111.43 (16)
C11—C12—H12	119.0	C22—C23—H23A	109.3
C13—C12—H12	119.0	C24—C23—H23A	109.3
C14—C13—C12	120.4 (2)	C22—C23—H23B	109.3
C14—C13—C18	120.0 (2)	C24—C23—H23B	109.3
C12—C13—C18	119.57 (18)	H23A—C23—H23B	108.0
C15—C14—C13	121.8 (2)	C25—C24—C23	111.42 (19)
C15—C14—H14	119.1	C25—C24—H24A	109.3
C13—C14—H14	119.1	C23—C24—H24A	109.3
C14—C15—C16	118.7 (2)	C25—C24—H24B	109.3
C14—C15—H15	120.6	C23—C24—H24B	109.3
C16—C15—H15	120.6	H24A—C24—H24B	108.0
C17—C16—C15	121.6 (2)	N5—C25—C24	109.06 (15)
C17—C16—H16	119.2	N5—C25—H25A	109.9
C15—C16—H16	119.2	C24—C25—H25A	109.9
C16—C17—C18	122.2 (2)	N5—C25—H25B	109.9
C16—C17—H17	118.9	C24—C25—H25B	109.9
C18—C17—H17	118.9	H25A—C25—H25B	108.3
C17—C18—C13	115.63 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O4ⁱ	0.93	2.56	3.308 (2)	138

Symmetry code: (i) −x, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₉NO₂S₂
M_r	369.48
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	12.4508 (3), 10.1924 (3), 14.0188 (4)
β (°)	100.953 (2)
V (Å³)	1746.63 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.24 × 0.20 × 0.12

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.770, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	12000, 2993, 2380
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.593

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.082, 1.06
No. of reflections	2993
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.14

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O4ⁱ	0.93	2.56	3.308 (2)	138

Symmetry code: (i) −x, y+1/2, −z+3/2.

Acknowledgements

The authors thank the Universities Sophisticated Instrumental Centre, Karnatak University, Dharwad, for the X-ray data collection and the GCMS, IR, CHNS and NMR data. KMK is grateful to Karnatak Science College, Dharwad, for providing laboratory facilities.

References

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Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin,USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar