(3-Oxo-3H-benzo[f]chromen-1-yl)methyl N,N-dimethyl­carbamodithio­ate

Mahabaleshwaraiah, N.M.; Ravi, H.R.; Vinduvahini, M.; Sreepad, H.R.; Kotresh, O.

doi:10.1107/S160053681203975X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page o3001

https://doi.org/10.1107/S160053681203975X

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(3-Oxo-3H-benzo[f]chromen-1-yl)methyl N,N-dimethylcarbamodithioate

N. M. Mahabaleshwaraiah,^a H. R. Ravi,^b M. Vinduvahini,^c ^* H. R. Sreepad ^b and O. Kotresh ^a

^aDepartment of Chemistry, Karnatak University's Karnatak Science College, Dharwad, Karnataka 580 001, India, ^bResearch Centre, Postgraduate Department of Physics, Government First Grade College (Autonomous), Mandya 571 401, Karnataka, India, and ^cDepartment of Physics, Sri D Devaraja Urs Government First Grade College, Hunsur 571 105, Mysore District, Karnataka, India
^*Correspondence e-mail: vinduvahinim@yahoo.in

(Received 21 August 2012; accepted 19 September 2012; online 26 September 2012)

In the title compound, C₁₇H₁₅NO₂S₂, the 3H-benzo[f]chromene ring system is distinctly twisted; the dihedral angle between the pyran ring and its opposite benzene ring is 9.11 (8)°. The N,N-dimethylcarbamodithioate residue lies almost perpendicular to the pyran ring [dihedral angle = 85.15 (7)°]. In the crystal, weak C—H⋯O hydrogen bonds link the molecules into C(10) chains propagating in [001].

Related literature

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

Experimental

Crystal data

C₁₇H₁₅NO₂S₂
M_r = 329.42
Monoclinic, P 2₁ /n
a = 14.1575 (2) Å
b = 6.9399 (1) Å
c = 15.9750 (2) Å
β = 101.591 (1)°
V = 1537.56 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 296 K
0.24 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.770, T_max = 1.000
14561 measured reflections
2708 independent reflections
2387 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.104
S = 1.06
2708 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2ⁱ	0.93	2.51	3.405 (3)	162
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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: https://doi.org/10.1107/S160053681203975X/hb6942sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681203975X/hb6942Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681203975X/hb6942Isup3.cml

checkCIF report

Related literature top

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

Experimental top

The title compound was synthesized according to the reported method (Kumar et al., 2012). It was recrystallized from an ethanol–chloroform solvent mixture as colourless plates. Yield = 81%, m.p. 435 K.

Structure description top

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

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. The H atoms are shown as spheres of arbitrary radii.
	Fig. 2. Packing of the molecules.

(3-oxo-3H-benzo[f]chromen-1-yl)methyl N,N-dimethylcarbamodithioate top

Crystal data top

C₁₇H₁₅NO₂S₂	F(000) = 688
M_r = 329.42	D_x = 1.423 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 435 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 14.1575 (2) Å	Cell parameters from 2708 reflections
b = 6.9399 (1) Å	θ = 1.8–25.0°
c = 15.9750 (2) Å	µ = 0.35 mm⁻¹
β = 101.591 (1)°	T = 296 K
V = 1537.56 (4) Å³	Plate, colourless
Z = 4	0.24 × 0.20 × 0.12 mm

Data collection top

Bruker SMART CCD diffractometer	2708 independent reflections
Radiation source: fine-focus sealed tube	2387 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω and φ scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −16→16
T_min = 0.770, T_max = 1.000	k = −8→8
14561 measured reflections	l = −18→18

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) = 0.104	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0638P)² + 0.371P] where P = (F_o² + 2F_c²)/3
2708 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₇H₁₅NO₂S₂	V = 1537.56 (4) Å³
M_r = 329.42	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.1575 (2) Å	µ = 0.35 mm⁻¹
b = 6.9399 (1) Å	T = 296 K
c = 15.9750 (2) Å	0.24 × 0.20 × 0.12 mm
β = 101.591 (1)°

Data collection top

Bruker SMART CCD diffractometer	2708 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2387 reflections with I > 2σ(I)
T_min = 0.770, T_max = 1.000	R_int = 0.023
14561 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.06	Δρ_max = 0.28 e Å⁻³
2708 reflections	Δρ_min = −0.24 e Å⁻³
199 parameters

Special details top

Experimental. IR (KBr): 660 cm^-1 (C—S), 1251 cm^-1 (C═S), 1036 cm^-1 (C—O), 842 cm^-1 (C—N), 1279 cm^-1 (C—O—C), 1708.6 cm^-1 (C═O). GCMS: m/e: 335. 1H NMR (400 MHz, DMSO.D₆, δ, p.p.m.): 1.92 (m, 2H, C₁₀), 2.01 (m, 2H, C₁), 2.49 (m, 4H, C₂, C₁₁), 3.80 (s, 3H, C₉), 4.86 (s, 2H, C₄), 6.57 (s, 1H, C₁₂), 7.24 (m, 1H, C₁₅), 7.36 (t, 1H, C₇), 7.38 (s, 1H, C₁₆). Elemental analysis: C, 57.26; H, 5.07; N, 4.15.

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	−0.10475 (3)	0.58858 (7)	0.13224 (3)	0.04867 (17)
S2	−0.13511 (3)	1.01975 (7)	0.13357 (4)	0.05409 (18)
O1	0.15254 (9)	0.74478 (19)	0.41212 (8)	0.0436 (3)
O2	0.01004 (11)	0.7691 (3)	0.44665 (9)	0.0652 (4)
N1	−0.27082 (10)	0.7553 (3)	0.12911 (10)	0.0488 (4)
C1	0.41046 (13)	0.7183 (3)	0.19340 (13)	0.0456 (4)
H1	0.4754	0.7065	0.2185	0.055*
C2	0.38414 (14)	0.7329 (3)	0.10721 (13)	0.0508 (5)
H2	0.4303	0.7288	0.0733	0.061*
C3	0.28694 (14)	0.7539 (3)	0.07027 (13)	0.0499 (5)
H3	0.2688	0.7681	0.0113	0.060*
C4	0.21747 (13)	0.7542 (3)	0.11888 (11)	0.0416 (4)
H4	0.1532	0.7687	0.0921	0.050*
C5	0.24097 (12)	0.7331 (2)	0.20858 (11)	0.0328 (4)
C6	0.34099 (12)	0.7208 (2)	0.24588 (12)	0.0366 (4)
C7	0.17168 (11)	0.7307 (2)	0.26443 (10)	0.0314 (3)
C8	0.20897 (12)	0.7360 (2)	0.35158 (11)	0.0354 (4)
C9	0.30765 (13)	0.7276 (3)	0.38766 (12)	0.0435 (4)
H9	0.3286	0.7302	0.4467	0.052*
C10	0.37191 (12)	0.7158 (3)	0.33586 (12)	0.0426 (4)
H10	0.4373	0.7042	0.3595	0.051*
C11	0.06649 (11)	0.7181 (2)	0.23967 (11)	0.0339 (4)
C12	0.01393 (12)	0.7310 (3)	0.30092 (12)	0.0409 (4)
H12	−0.0529	0.7268	0.2842	0.049*
C13	0.05420 (13)	0.7508 (3)	0.38989 (12)	0.0446 (4)
C14	0.01533 (12)	0.6860 (3)	0.14798 (11)	0.0404 (4)
H14A	0.0544	0.5996	0.1213	0.048*
H14B	0.0123	0.8083	0.1181	0.048*
C15	−0.17873 (12)	0.7969 (3)	0.13185 (11)	0.0397 (4)
C16	−0.31006 (16)	0.5603 (4)	0.12493 (16)	0.0676 (6)
H16A	−0.3781	0.5660	0.1236	0.101*
H16B	−0.2789	0.4888	0.1742	0.101*
H16C	−0.2990	0.4977	0.0742	0.101*
C17	−0.34233 (14)	0.9085 (4)	0.12752 (16)	0.0668 (6)
H17A	−0.4046	0.8523	0.1258	0.100*
H17B	−0.3443	0.9873	0.0778	0.100*
H17C	−0.3249	0.9863	0.1779	0.100*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0357 (3)	0.0472 (3)	0.0603 (3)	−0.00403 (19)	0.0030 (2)	−0.0062 (2)
S2	0.0350 (3)	0.0487 (3)	0.0741 (4)	−0.0002 (2)	0.0003 (2)	0.0049 (2)
O1	0.0400 (7)	0.0563 (7)	0.0364 (6)	0.0031 (5)	0.0123 (5)	0.0014 (5)
O2	0.0541 (9)	0.0994 (12)	0.0492 (8)	0.0075 (8)	0.0273 (7)	0.0011 (8)
N1	0.0305 (8)	0.0658 (10)	0.0500 (9)	−0.0064 (7)	0.0073 (7)	−0.0073 (8)
C1	0.0313 (9)	0.0448 (10)	0.0642 (12)	0.0016 (7)	0.0176 (8)	0.0010 (9)
C2	0.0462 (11)	0.0542 (11)	0.0603 (12)	0.0013 (8)	0.0305 (10)	0.0005 (9)
C3	0.0536 (12)	0.0564 (11)	0.0447 (10)	0.0038 (9)	0.0214 (9)	0.0036 (9)
C4	0.0372 (9)	0.0475 (10)	0.0422 (9)	0.0035 (7)	0.0125 (8)	0.0037 (8)
C5	0.0327 (8)	0.0267 (7)	0.0406 (9)	0.0024 (6)	0.0107 (7)	0.0020 (6)
C6	0.0330 (9)	0.0291 (8)	0.0492 (10)	0.0002 (6)	0.0123 (7)	0.0009 (7)
C7	0.0294 (8)	0.0272 (7)	0.0385 (9)	0.0031 (6)	0.0090 (6)	0.0025 (6)
C8	0.0365 (9)	0.0336 (8)	0.0381 (9)	0.0015 (6)	0.0116 (7)	0.0017 (7)
C9	0.0397 (10)	0.0493 (10)	0.0393 (9)	−0.0007 (8)	0.0026 (7)	0.0006 (8)
C10	0.0291 (8)	0.0437 (10)	0.0525 (10)	0.0000 (7)	0.0025 (7)	0.0017 (8)
C11	0.0311 (8)	0.0318 (8)	0.0393 (9)	0.0039 (6)	0.0080 (7)	0.0027 (6)
C12	0.0295 (8)	0.0464 (10)	0.0476 (10)	0.0032 (7)	0.0097 (7)	0.0041 (8)
C13	0.0395 (10)	0.0511 (10)	0.0463 (10)	0.0044 (8)	0.0163 (8)	0.0042 (8)
C14	0.0305 (8)	0.0471 (10)	0.0439 (9)	0.0031 (7)	0.0082 (7)	−0.0025 (7)
C15	0.0298 (8)	0.0539 (11)	0.0334 (8)	−0.0012 (7)	0.0019 (6)	−0.0023 (7)
C16	0.0446 (12)	0.0797 (16)	0.0781 (15)	−0.0233 (11)	0.0115 (11)	−0.0075 (13)
C17	0.0313 (10)	0.0920 (18)	0.0773 (15)	0.0048 (10)	0.0113 (10)	−0.0135 (13)

Geometric parameters (Å, º) top

S1—C15	1.7844 (18)	C6—C10	1.416 (3)
S1—C14	1.7997 (17)	C7—C8	1.387 (2)
S2—C15	1.6637 (18)	C7—C11	1.465 (2)
O1—C13	1.367 (2)	C8—C9	1.401 (2)
O1—C8	1.374 (2)	C9—C10	1.350 (3)
O2—C13	1.207 (2)	C9—H9	0.9300
N1—C15	1.327 (2)	C10—H10	0.9300
N1—C16	1.460 (3)	C11—C12	1.346 (2)
N1—C17	1.465 (3)	C11—C14	1.514 (2)
C1—C2	1.356 (3)	C12—C13	1.428 (3)
C1—C6	1.415 (2)	C12—H12	0.9300
C1—H1	0.9300	C14—H14A	0.9700
C2—C3	1.392 (3)	C14—H14B	0.9700
C2—H2	0.9300	C16—H16A	0.9600
C3—C4	1.370 (2)	C16—H16B	0.9600
C3—H3	0.9300	C16—H16C	0.9600
C4—C5	1.412 (2)	C17—H17A	0.9600
C4—H4	0.9300	C17—H17B	0.9600
C5—C6	1.424 (2)	C17—H17C	0.9600
C5—C7	1.453 (2)

C15—S1—C14	103.50 (8)	C9—C10—H10	119.6
C13—O1—C8	121.63 (14)	C6—C10—H10	119.6
C15—N1—C16	124.41 (17)	C12—C11—C7	118.71 (15)
C15—N1—C17	120.92 (18)	C12—C11—C14	119.09 (15)
C16—N1—C17	114.64 (17)	C7—C11—C14	122.18 (14)
C2—C1—C6	121.25 (17)	C11—C12—C13	124.16 (16)
C2—C1—H1	119.4	C11—C12—H12	117.9
C6—C1—H1	119.4	C13—C12—H12	117.9
C1—C2—C3	119.01 (17)	O2—C13—O1	117.55 (17)
C1—C2—H2	120.5	O2—C13—C12	126.46 (18)
C3—C2—H2	120.5	O1—C13—C12	115.97 (15)
C4—C3—C2	121.41 (19)	C11—C14—S1	116.43 (12)
C4—C3—H3	119.3	C11—C14—H14A	108.2
C2—C3—H3	119.3	S1—C14—H14A	108.2
C3—C4—C5	121.69 (17)	C11—C14—H14B	108.2
C3—C4—H4	119.2	S1—C14—H14B	108.2
C5—C4—H4	119.2	H14A—C14—H14B	107.3
C4—C5—C6	116.26 (15)	N1—C15—S2	124.15 (14)
C4—C5—C7	125.03 (15)	N1—C15—S1	113.33 (14)
C6—C5—C7	118.66 (15)	S2—C15—S1	122.51 (10)
C1—C6—C10	119.42 (16)	N1—C16—H16A	109.5
C1—C6—C5	120.26 (17)	N1—C16—H16B	109.5
C10—C6—C5	120.31 (15)	H16A—C16—H16B	109.5
C8—C7—C5	116.65 (15)	N1—C16—H16C	109.5
C8—C7—C11	115.72 (14)	H16A—C16—H16C	109.5
C5—C7—C11	127.61 (15)	H16B—C16—H16C	109.5
O1—C8—C7	123.37 (15)	N1—C17—H17A	109.5
O1—C8—C9	112.63 (15)	N1—C17—H17B	109.5
C7—C8—C9	123.98 (15)	H17A—C17—H17B	109.5
C10—C9—C8	119.30 (17)	N1—C17—H17C	109.5
C10—C9—H9	120.4	H17A—C17—H17C	109.5
C8—C9—H9	120.4	H17B—C17—H17C	109.5
C9—C10—C6	120.78 (16)

C6—C1—C2—C3	1.1 (3)	C8—C9—C10—C6	3.0 (3)
C1—C2—C3—C4	−2.0 (3)	C1—C6—C10—C9	176.69 (17)
C2—C3—C4—C5	−0.1 (3)	C5—C6—C10—C9	−1.8 (3)
C3—C4—C5—C6	2.9 (3)	C8—C7—C11—C12	6.2 (2)
C3—C4—C5—C7	−179.57 (17)	C5—C7—C11—C12	−175.55 (15)
C2—C1—C6—C10	−176.61 (17)	C8—C7—C11—C14	−172.20 (15)
C2—C1—C6—C5	1.9 (3)	C5—C7—C11—C14	6.1 (2)
C4—C5—C6—C1	−3.8 (2)	C7—C11—C12—C13	−1.9 (3)
C7—C5—C6—C1	178.55 (15)	C14—C11—C12—C13	176.53 (16)
C4—C5—C6—C10	174.68 (15)	C8—O1—C13—O2	−176.03 (17)
C7—C5—C6—C10	−3.0 (2)	C8—O1—C13—C12	5.1 (2)
C4—C5—C7—C8	−171.14 (16)	C11—C12—C13—O2	177.5 (2)
C6—C5—C7—C8	6.3 (2)	C11—C12—C13—O1	−3.8 (3)
C4—C5—C7—C11	10.6 (3)	C12—C11—C14—S1	−20.2 (2)
C6—C5—C7—C11	−171.94 (15)	C7—C11—C14—S1	158.21 (12)
C13—O1—C8—C7	−0.7 (2)	C15—S1—C14—C11	86.48 (14)
C13—O1—C8—C9	−178.99 (16)	C16—N1—C15—S2	178.01 (16)
C5—C7—C8—O1	176.45 (14)	C17—N1—C15—S2	−0.1 (3)
C11—C7—C8—O1	−5.1 (2)	C16—N1—C15—S1	−1.3 (2)
C5—C7—C8—C9	−5.4 (2)	C17—N1—C15—S1	−179.39 (14)
C11—C7—C8—C9	173.06 (15)	C14—S1—C15—N1	−173.89 (13)
O1—C8—C9—C10	179.10 (16)	C14—S1—C15—S2	6.82 (14)
C7—C8—C9—C10	0.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ⁱ	0.93	2.51	3.405 (3)	162

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅NO₂S₂
M_r	329.42
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	14.1575 (2), 6.9399 (1), 15.9750 (2)
β (°)	101.591 (1)
V (Å³)	1537.56 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.24 × 0.20 × 0.12

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.770, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	14561, 2708, 2387
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.104, 1.06
No. of reflections	2708
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.24

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
C2—H2···O2ⁱ	0.93	2.51	3.405 (3)	162

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

Acknowledgements

The authors acknowledge the Universities Sophisticated Instrumental Centre, Karnatak University, Dharwad, for measuring the single-crystal X-ray data and providing the chemical analysis (GCMS, IR, CHNS and NMR data). NM is grateful to Karnatak Science College, Dharwad, for providing laboratory facilities. He is also grateful to P. C. Jabin Science College, Hubli and the UGC for support under the FIP.

References

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