(6-Meth­oxy-2-oxo-2H-chromen-4-yl)methyl morpholine-4-carbodithio­ate

Devarajegowda, H.C.; Kumar, K.M.; Seenivasa, S.; Arunkashi, H.K.; Kotresh, O.

doi:10.1107/S1600536812051847

organic compounds

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Volume 69| Part 2| February 2013| Page o192

doi:10.1107/S1600536812051847

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(6-Methoxy-2-oxo-2H-chromen-4-yl)methyl morpholine-4-carbodithioate

H. C. Devarajegowda,^a ^* K. Mahesh Kumar,^b S. Seenivasa,^c H. K. Arunkashi ^a and O. Kotresh ^b

^aDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India, ^bDepartment of Chemistry, Karnatak University's Karnatak Science College, Dharwad, Karnataka 580 001, India, and ^cDeapartment of Studies and Research in Chemistry, Tumkur University, Tumkur 572 103, Karnataka, India
^*Correspondence e-mail: devarajegowda@yahoo.com

(Received 2 November 2012; accepted 25 December 2012; online 9 January 2013)

In the title compound, C₁₆H₁₇NO₄S₂, the 2H-chromene ring system is nearly planar, with a maximum deviation of 0.070 (1) Å, and the morpholine ring adopts a chair conformation; the bond-angle sum for its N atom is 357.9°. The dihedral angle between the the 2H-chromene ring and the best plane through the morpholine ring is 89.09 (6)°. An intramolecular C—H⋯S hydrogen bond occurs. In the crystal, C—H⋯O hydrogen bonds generate R₂²(8) rings and π–π interactions occur between fused benzene rings of the chromene system [shortest centroid–centroid distance = 3.5487 (8) Å].

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

C₁₆H₁₇NO₄S₂
M_r = 351.43
Triclinic, $[P \overline 1]$
a = 7.0026 (5) Å
b = 7.9939 (6) Å
c = 14.8033 (11) Å
α = 75.433 (4)°
β = 86.642 (4)°
γ = 78.355 (4)°
V = 785.49 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 296 K
0.24 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.770, T_max = 1.000
13583 measured reflections
2725 independent reflections
2482 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.073
S = 1.06
2725 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O6ⁱ	0.93	2.55	3.4582 (19)	166
C17—H17B⋯O3ⁱⁱ	0.96	2.57	3.386 (2)	143
C18—H18B⋯S2	0.97	2.55	3.1527 (14)	120
Symmetry codes: (i) -x-1, -y+1, -z+1; (ii) x, y-1, z.

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 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812051847/gw2129sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812051847/gw2129Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812051847/gw2129Isup3.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 (6-methoxy-2-oxo-2H-chromen-4-yl) methyl morpholine-4-carbodithioate.

The asymmetric unit of (6-methoxy-2-oxo-2H-chromen-4-yl)methyl morpholine-4-carbodithioate is shown in Fig. 1. The 2H-chromene ring system (O3/C8–C16) is essentially planar, with a maximum deviation of 0.070 (1) Å for atom C8 and the morpholine ring adopts a chair conformation: the bond-angle sum for its N7 atom is 357.9 Å. The dihedral angle between the 2H-chromene (O3/C8–C16) ring and the morpholine (N7/O5/C20–C23) ring is 89.09 (6)°. In the crystal structure, (Fig. 2), intermolecular C14—H14···O6 and C17B—H17B···O3 and intramolecular C18—H18B···S2 hydrogen bonds observed and also π–π interactions between fused benzene Cg₍₃₎ (C11–C16) rings of chromene [shortest centroid–centroid distance = 3.5487 (8) Å] further stabilize the crystal packing

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. Colour: yellowish. Yield= 84%, m.p.481 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, 2012); 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.
	Fig. 2. The packing of molecules.

(6-Methoxy-2-oxo-2H-chromen-4-yl)methyl morpholine-4-carbodithioate top

Crystal data top

C₁₆H₁₇NO₄S₂	Z = 2
M_r = 351.43	F(000) = 368
Triclinic, P1	D_x = 1.486 Mg m⁻³
Hall symbol: -P 1	Melting point: 481 K
a = 7.0026 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.9939 (6) Å	Cell parameters from 2725 reflections
c = 14.8033 (11) Å	θ = 2.7–25.0°
α = 75.433 (4)°	µ = 0.36 mm⁻¹
β = 86.642 (4)°	T = 296 K
γ = 78.355 (4)°	Plate, colourless
V = 785.49 (10) Å³	0.24 × 0.20 × 0.12 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2725 independent reflections
Radiation source: fine-focus sealed tube	2482 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω and ϕ scans	θ_max = 25.0°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −8→8
T_min = 0.770, T_max = 1.000	k = −9→9
13583 measured reflections	l = −17→17

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.073	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0403P)² + 0.1479P] where P = (F_o² + 2F_c²)/3
2725 reflections	(Δ/σ)_max = 0.001
208 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₆H₁₇NO₄S₂	γ = 78.355 (4)°
M_r = 351.43	V = 785.49 (10) Å³
Triclinic, P1	Z = 2
a = 7.0026 (5) Å	Mo Kα radiation
b = 7.9939 (6) Å	µ = 0.36 mm⁻¹
c = 14.8033 (11) Å	T = 296 K
α = 75.433 (4)°	0.24 × 0.20 × 0.12 mm
β = 86.642 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2725 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	2482 reflections with I > 2σ(I)
T_min = 0.770, T_max = 1.000	R_int = 0.024
13583 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.073	H-atom parameters constrained
S = 1.06	Δρ_max = 0.21 e Å⁻³
2725 reflections	Δρ_min = −0.15 e Å⁻³
208 parameters

Special details top

Experimental. IR (KBr): 662 cm^-1(C—S), 1233 cm^-11 (C=S), 1032 cm^-1(C—O), 842 cm^-1 (C—N),1118 cm^-1(C—O—C), 1703 cm^-1(C=O). GCMS: m/e: 335. 1H NMR (400 MHz, CDCl₃, \?, p.p.m.) 1.91 (m, 6H, Morpholine-CH₂), 2.34 (s, 4H, Morpholine –CH₂), 4.63 (d, 2H, Methylene-CH₂),5.88(s, 1H, Ar—H), 6.39 (s, 1H, Ar—H), 7.08 (s, 1H, Ar—H), 7.12 (s, 1H, Ar—H). Elemental analysis for C₁₆H₁₇NO₃S₂: C, 57.21; H, 5.04; N, 4.11.

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	0.20243 (5)	0.57411 (5)	0.13634 (2)	0.03769 (12)
S2	0.56769 (5)	0.71727 (6)	0.06898 (3)	0.04523 (13)
O3	0.11086 (15)	0.92127 (12)	0.39849 (7)	0.0387 (2)
O4	0.3416 (2)	1.06890 (16)	0.34092 (10)	0.0637 (3)
O5	0.05206 (16)	0.92565 (15)	−0.20255 (7)	0.0481 (3)
O6	−0.32490 (16)	0.41563 (13)	0.41094 (8)	0.0478 (3)
N7	0.25269 (16)	0.75947 (14)	−0.03248 (8)	0.0338 (3)
C8	0.2732 (2)	0.94051 (19)	0.34374 (10)	0.0423 (3)
C9	0.3469 (2)	0.80463 (19)	0.29565 (10)	0.0391 (3)
H9	0.4639	0.8085	0.2627	0.047*
C10	0.2545 (2)	0.67253 (17)	0.29619 (9)	0.0316 (3)
C11	0.0733 (2)	0.66496 (16)	0.34768 (8)	0.0302 (3)
C12	0.0084 (2)	0.79116 (16)	0.39807 (9)	0.0322 (3)
C13	−0.1612 (2)	0.79099 (18)	0.45089 (9)	0.0380 (3)
H13	−0.2017	0.8758	0.4846	0.046*
C14	−0.2691 (2)	0.66436 (19)	0.45309 (10)	0.0396 (3)
H14	−0.3836	0.6639	0.4882	0.047*
C15	−0.2080 (2)	0.53636 (17)	0.40304 (9)	0.0355 (3)
C16	−0.0384 (2)	0.53634 (17)	0.35082 (9)	0.0336 (3)
H16	0.0020	0.4508	0.3176	0.040*
C17	−0.2599 (2)	0.2748 (2)	0.36796 (13)	0.0518 (4)
H17A	−0.3539	0.1994	0.3787	0.078*
H17B	−0.1370	0.2086	0.3939	0.078*
H17C	−0.2448	0.3208	0.3020	0.078*
C18	0.3358 (2)	0.53685 (18)	0.24300 (9)	0.0353 (3)
H18A	0.3293	0.4206	0.2818	0.042*
H18B	0.4718	0.5408	0.2280	0.042*
C19	0.34447 (19)	0.69401 (16)	0.04920 (9)	0.0311 (3)
C20	0.0686 (2)	0.71676 (19)	−0.05329 (10)	0.0407 (3)
H20A	−0.0043	0.6857	0.0042	0.049*
H20B	0.0962	0.6156	−0.0802	0.049*
C21	−0.0524 (2)	0.8689 (2)	−0.11983 (11)	0.0441 (4)
H21A	−0.1690	0.8341	−0.1351	0.053*
H21B	−0.0923	0.9658	−0.0901	0.053*
C22	0.2181 (2)	0.9831 (2)	−0.18091 (11)	0.0497 (4)
H22A	0.1762	1.0806	−0.1518	0.060*
H22B	0.2864	1.0260	−0.2383	0.060*
C23	0.3561 (2)	0.8398 (2)	−0.11672 (10)	0.0430 (3)
H23A	0.4142	0.7502	−0.1491	0.052*
H23B	0.4600	0.8887	−0.0989	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0381 (2)	0.0462 (2)	0.0334 (2)	−0.01826 (16)	0.00258 (14)	−0.01081 (15)
S2	0.0298 (2)	0.0622 (3)	0.0451 (2)	−0.01602 (17)	−0.00144 (16)	−0.00997 (18)
O3	0.0470 (6)	0.0347 (5)	0.0383 (5)	−0.0103 (4)	−0.0010 (4)	−0.0142 (4)
O4	0.0665 (8)	0.0560 (7)	0.0859 (9)	−0.0322 (6)	0.0105 (7)	−0.0352 (6)
O5	0.0433 (6)	0.0585 (7)	0.0405 (6)	−0.0172 (5)	−0.0066 (5)	−0.0014 (5)
O6	0.0432 (6)	0.0412 (6)	0.0627 (7)	−0.0158 (5)	0.0115 (5)	−0.0164 (5)
N7	0.0285 (6)	0.0383 (6)	0.0351 (6)	−0.0111 (5)	0.0005 (5)	−0.0066 (5)
C8	0.0440 (9)	0.0426 (8)	0.0438 (8)	−0.0140 (7)	−0.0039 (7)	−0.0118 (6)
C9	0.0347 (8)	0.0430 (8)	0.0414 (8)	−0.0098 (6)	0.0002 (6)	−0.0118 (6)
C10	0.0328 (7)	0.0316 (6)	0.0278 (6)	−0.0024 (5)	−0.0047 (5)	−0.0045 (5)
C11	0.0343 (7)	0.0283 (6)	0.0254 (6)	−0.0030 (5)	−0.0039 (5)	−0.0032 (5)
C12	0.0397 (8)	0.0283 (6)	0.0274 (6)	−0.0052 (6)	−0.0052 (6)	−0.0044 (5)
C13	0.0457 (9)	0.0344 (7)	0.0323 (7)	−0.0020 (6)	0.0026 (6)	−0.0107 (6)
C14	0.0400 (8)	0.0397 (7)	0.0356 (7)	−0.0049 (6)	0.0065 (6)	−0.0067 (6)
C15	0.0372 (8)	0.0307 (7)	0.0361 (7)	−0.0076 (6)	−0.0006 (6)	−0.0029 (5)
C16	0.0397 (8)	0.0279 (6)	0.0331 (7)	−0.0042 (6)	0.0001 (6)	−0.0090 (5)
C17	0.0464 (9)	0.0387 (8)	0.0733 (11)	−0.0102 (7)	−0.0034 (8)	−0.0174 (8)
C18	0.0342 (7)	0.0351 (7)	0.0344 (7)	−0.0033 (6)	−0.0012 (6)	−0.0072 (5)
C19	0.0292 (7)	0.0295 (6)	0.0366 (7)	−0.0051 (5)	0.0034 (5)	−0.0127 (5)
C20	0.0337 (8)	0.0456 (8)	0.0436 (8)	−0.0170 (6)	−0.0039 (6)	−0.0041 (6)
C21	0.0327 (8)	0.0516 (9)	0.0454 (8)	−0.0084 (7)	−0.0024 (6)	−0.0068 (7)
C22	0.0481 (10)	0.0533 (9)	0.0456 (9)	−0.0225 (8)	−0.0038 (7)	0.0023 (7)
C23	0.0342 (8)	0.0559 (9)	0.0381 (8)	−0.0149 (7)	0.0036 (6)	−0.0061 (7)

Geometric parameters (Å, º) top

S1—C19	1.7846 (13)	C13—C14	1.373 (2)
S1—C18	1.8107 (14)	C13—H13	0.9300
S2—C19	1.6620 (14)	C14—C15	1.395 (2)
O3—C8	1.3682 (18)	C14—H14	0.9300
O3—C12	1.3792 (16)	C15—C16	1.378 (2)
O4—C8	1.2083 (18)	C16—H16	0.9300
O5—C21	1.4105 (19)	C17—H17A	0.9600
O5—C22	1.4136 (19)	C17—H17B	0.9600
O6—C15	1.3661 (17)	C17—H17C	0.9600
O6—C17	1.4134 (19)	C18—H18A	0.9700
N7—C19	1.3363 (17)	C18—H18B	0.9700
N7—C20	1.4662 (18)	C20—C21	1.499 (2)
N7—C23	1.4733 (18)	C20—H20A	0.9700
C8—C9	1.440 (2)	C20—H20B	0.9700
C9—C10	1.344 (2)	C21—H21A	0.9700
C9—H9	0.9300	C21—H21B	0.9700
C10—C11	1.4453 (19)	C22—C23	1.504 (2)
C10—C18	1.4995 (18)	C22—H22A	0.9700
C11—C12	1.3909 (19)	C22—H22B	0.9700
C11—C16	1.4028 (19)	C23—H23A	0.9700
C12—C13	1.383 (2)	C23—H23B	0.9700

C19—S1—C18	103.85 (6)	O6—C17—H17C	109.5
C8—O3—C12	121.50 (11)	H17A—C17—H17C	109.5
C21—O5—C22	109.50 (12)	H17B—C17—H17C	109.5
C15—O6—C17	117.51 (12)	C10—C18—S1	111.36 (9)
C19—N7—C20	124.03 (11)	C10—C18—H18A	109.4
C19—N7—C23	120.79 (12)	S1—C18—H18A	109.4
C20—N7—C23	113.08 (11)	C10—C18—H18B	109.4
O4—C8—O3	117.00 (14)	S1—C18—H18B	109.4
O4—C8—C9	126.27 (15)	H18A—C18—H18B	108.0
O3—C8—C9	116.73 (12)	N7—C19—S2	124.57 (10)
C10—C9—C8	122.97 (14)	N7—C19—S1	112.68 (10)
C10—C9—H9	118.5	S2—C19—S1	122.74 (8)
C8—C9—H9	118.5	N7—C20—C21	111.40 (12)
C9—C10—C11	118.87 (13)	N7—C20—H20A	109.3
C9—C10—C18	120.67 (13)	C21—C20—H20A	109.3
C11—C10—C18	120.46 (12)	N7—C20—H20B	109.3
C12—C11—C16	118.41 (13)	C21—C20—H20B	109.3
C12—C11—C10	117.82 (12)	H20A—C20—H20B	108.0
C16—C11—C10	123.77 (12)	O5—C21—C20	111.41 (12)
O3—C12—C13	116.84 (12)	O5—C21—H21A	109.3
O3—C12—C11	121.63 (12)	C20—C21—H21A	109.3
C13—C12—C11	121.52 (13)	O5—C21—H21B	109.3
C14—C13—C12	119.35 (13)	C20—C21—H21B	109.3
C14—C13—H13	120.3	H21A—C21—H21B	108.0
C12—C13—H13	120.3	O5—C22—C23	112.76 (13)
C13—C14—C15	120.46 (13)	O5—C22—H22A	109.0
C13—C14—H14	119.8	C23—C22—H22A	109.0
C15—C14—H14	119.8	O5—C22—H22B	109.0
O6—C15—C16	124.29 (13)	C23—C22—H22B	109.0
O6—C15—C14	115.64 (13)	H22A—C22—H22B	107.8
C16—C15—C14	120.07 (13)	N7—C23—C22	110.63 (12)
C15—C16—C11	120.20 (12)	N7—C23—H23A	109.5
C15—C16—H16	119.9	C22—C23—H23A	109.5
C11—C16—H16	119.9	N7—C23—H23B	109.5
O6—C17—H17A	109.5	C22—C23—H23B	109.5
O6—C17—H17B	109.5	H23A—C23—H23B	108.1
H17A—C17—H17B	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O6ⁱ	0.93	2.55	3.4582 (19)	166
C17—H17B···O3ⁱⁱ	0.96	2.57	3.386 (2)	143
C18—H18B···S2	0.97	2.55	3.1527 (14)	120

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₇NO₄S₂
M_r	351.43
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.0026 (5), 7.9939 (6), 14.8033 (11)
α, β, γ (°)	75.433 (4), 86.642 (4), 78.355 (4)
V (Å³)	785.49 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.24 × 0.20 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector 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	13583, 2725, 2482
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.073, 1.06
No. of reflections	2725
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.15

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O6ⁱ	0.93	2.5500	3.4582 (19)	166.00
C17—H17B···O3ⁱⁱ	0.96	2.5700	3.386 (2)	143.00
C18—H18B···S2	0.97	2.5500	3.1527 (14)	120.00

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

Acknowledgements

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

References

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