(2-Oxo-2H-benzo[h]chromen-4-yl)methyl morpholine-4-carbodithio-ate.

In the title compound, C(19)H(17)NO(3)S(2), the morpholine ring is in a chair conformation. In the coumarin ring system, the dihedral angle between the benzene and pyran rings is 3.9 (1)°. In the crystal, weak C-H⋯O inter-actions link the mol-ecules into corrugated layers parallel to (102). The crystal packing also exhibits π-π inter-actions, with distances of 3.644 (1) and 3.677 (1) Å between the centroids of the benzene rings of neighbouring mol-ecules.

Related literature

For the biological activity of coumarins, see: Kontogiorgis & Hadjipavlou-Litina (2004 ▶). For a related structure, see: Kumar et al. (2012 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C19H17NO3S2

M = 371.46

Monoclinic,

a = 13.0928 (4) Å

b = 11.6978 (3) Å

c = 11.3673 (3) Å

β = 99.232 (3)°

V = 1718.43 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 293 K

0.3 × 0.2 × 0.1 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.818, T max = 1.000

18655 measured reflections

3017 independent reflections

2457 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.104

S = 1.05

3017 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); 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: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681201094X/cv5260sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201094X/cv5260Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681201094X/cv5260Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H17NO3S2	F(000) = 776
Mr = 371.46	Dx = 1.436 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9000 reflections
a = 13.0928 (4) Å	θ = 3.5–29.0°
b = 11.6978 (3) Å	µ = 0.33 mm−1
c = 11.3673 (3) Å	T = 293 K
β = 99.232 (3)°	Plate shaped, light yellow
V = 1718.43 (8) Å3	0.3 × 0.2 × 0.1 mm
Z = 4

Oxford Diffraction Xcalibur Sapphire3 diffractometer	3017 independent reflections
Radiation source: fine-focus sealed tube	2457 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
Detector resolution: 16.1049 pixels mm-1	θmax = 25.0°, θmin = 3.5°
ω scans	h = −15→15
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −13→13
Tmin = 0.818, Tmax = 1.000	l = −13→13
18655 measured reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0471P)2 + 0.803P] where P = (Fo2 + 2Fc2)/3
3017 reflections	(Δ/σ)max = 0.001
226 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Experimental. CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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.

	x	y	z	Uiso*/Ueq
S1	0.85592 (4)	0.20784 (5)	0.78872 (5)	0.04418 (18)
S2	0.82222 (5)	0.40595 (6)	0.61667 (6)	0.0577 (2)
O1	0.74719 (10)	0.50873 (12)	1.10256 (12)	0.0393 (3)
O2	0.90505 (12)	0.56115 (14)	1.08171 (15)	0.0528 (4)
O3	1.20360 (13)	0.26933 (17)	0.65798 (18)	0.0683 (5)
N1	0.98691 (14)	0.26938 (16)	0.65122 (16)	0.0461 (5)
C1	0.74297 (15)	0.35148 (17)	0.91788 (17)	0.0359 (5)
C2	0.82708 (16)	0.41668 (18)	0.95188 (18)	0.0399 (5)
H2	0.8838	0.4079	0.9128	0.048*
C3	0.83295 (16)	0.49940 (18)	1.04603 (19)	0.0392 (5)
C4	0.66310 (15)	0.43868 (17)	1.07426 (18)	0.0342 (4)
C5	0.58582 (15)	0.45029 (18)	1.14826 (18)	0.0375 (5)
C6	0.59575 (18)	0.5245 (2)	1.2473 (2)	0.0478 (6)
H6	0.6539	0.5708	1.2654	0.057*
C7	0.5195 (2)	0.5279 (2)	1.3166 (2)	0.0594 (7)
H7	0.5270	0.5758	1.3828	0.071*
C8	0.4307 (2)	0.4611 (2)	1.2901 (2)	0.0594 (7)
H8	0.3795	0.4654	1.3379	0.071*
C9	0.41879 (17)	0.3897 (2)	1.1947 (2)	0.0523 (6)
H9	0.3592	0.3456	1.1776	0.063*
C10	0.49592 (15)	0.38159 (18)	1.12088 (19)	0.0405 (5)
C11	0.48607 (16)	0.30730 (19)	1.0208 (2)	0.0460 (5)
H11	0.4257	0.2650	1.0002	0.055*
C12	0.56292 (16)	0.29700 (19)	0.9549 (2)	0.0426 (5)
H12	0.5549	0.2463	0.8910	0.051*
C13	0.65541 (15)	0.36174 (17)	0.98100 (18)	0.0346 (4)
C14	0.73585 (16)	0.2666 (2)	0.8168 (2)	0.0455 (5)
H14A	0.7022	0.3037	0.7445	0.055*
H14B	0.6916	0.2040	0.8334	0.055*
C15	0.89538 (16)	0.29882 (18)	0.67899 (18)	0.0389 (5)
C16	1.03585 (19)	0.3310 (3)	0.5620 (2)	0.0592 (7)
H16A	0.9953	0.3981	0.5349	0.071*
H16B	1.0386	0.2820	0.4937	0.071*
C17	1.1420 (2)	0.3656 (3)	0.6158 (3)	0.0657 (7)
H17A	1.1743	0.4058	0.5568	0.079*
H17B	1.1385	0.4175	0.6815	0.079*
C18	1.15784 (19)	0.2117 (2)	0.7477 (2)	0.0595 (7)
H18A	1.1555	0.2632	0.8142	0.071*
H18B	1.2004	0.1466	0.7770	0.071*
C19	1.05149 (17)	0.1718 (2)	0.7007 (2)	0.0521 (6)
H19A	1.0540	0.1152	0.6389	0.063*
H19B	1.0213	0.1364	0.7642	0.063*

	U11	U22	U33	U12	U13	U23
S1	0.0474 (3)	0.0374 (3)	0.0509 (3)	0.0035 (2)	0.0176 (3)	−0.0012 (2)
S2	0.0595 (4)	0.0539 (4)	0.0601 (4)	0.0195 (3)	0.0114 (3)	0.0097 (3)
O1	0.0370 (8)	0.0371 (8)	0.0459 (8)	−0.0050 (6)	0.0130 (6)	−0.0069 (6)
O2	0.0448 (9)	0.0505 (10)	0.0661 (11)	−0.0162 (8)	0.0178 (8)	−0.0156 (8)
O3	0.0451 (10)	0.0716 (13)	0.0908 (13)	0.0030 (9)	0.0190 (9)	0.0225 (11)
N1	0.0415 (10)	0.0494 (11)	0.0487 (11)	0.0067 (9)	0.0109 (8)	0.0093 (9)
C1	0.0365 (11)	0.0320 (11)	0.0400 (11)	0.0015 (9)	0.0087 (9)	−0.0001 (9)
C2	0.0394 (12)	0.0378 (12)	0.0455 (12)	−0.0019 (10)	0.0159 (9)	−0.0023 (9)
C3	0.0372 (11)	0.0357 (11)	0.0466 (12)	−0.0024 (10)	0.0124 (9)	0.0001 (9)
C4	0.0310 (10)	0.0299 (10)	0.0423 (11)	0.0002 (8)	0.0074 (9)	0.0047 (9)
C5	0.0363 (11)	0.0339 (11)	0.0434 (11)	0.0075 (9)	0.0101 (9)	0.0071 (9)
C6	0.0471 (13)	0.0464 (13)	0.0523 (13)	0.0020 (11)	0.0157 (11)	−0.0034 (11)
C7	0.0645 (17)	0.0640 (17)	0.0547 (15)	0.0105 (14)	0.0241 (12)	−0.0039 (12)
C8	0.0524 (15)	0.0662 (17)	0.0668 (17)	0.0141 (13)	0.0317 (13)	0.0105 (14)
C9	0.0368 (12)	0.0556 (15)	0.0679 (16)	0.0036 (11)	0.0184 (11)	0.0114 (13)
C10	0.0320 (11)	0.0395 (12)	0.0513 (13)	0.0073 (9)	0.0104 (9)	0.0111 (10)
C11	0.0314 (11)	0.0433 (13)	0.0631 (15)	−0.0039 (10)	0.0066 (10)	0.0032 (11)
C12	0.0373 (11)	0.0397 (12)	0.0505 (12)	−0.0032 (10)	0.0059 (9)	−0.0035 (10)
C13	0.0313 (10)	0.0315 (10)	0.0412 (11)	0.0013 (9)	0.0062 (8)	0.0034 (9)
C14	0.0392 (12)	0.0473 (13)	0.0521 (13)	−0.0058 (10)	0.0142 (10)	−0.0126 (10)
C15	0.0411 (12)	0.0394 (12)	0.0365 (11)	0.0011 (9)	0.0076 (9)	−0.0043 (9)
C16	0.0541 (15)	0.0763 (18)	0.0482 (14)	0.0025 (13)	0.0117 (11)	0.0168 (13)
C17	0.0595 (16)	0.0668 (18)	0.0714 (17)	−0.0074 (14)	0.0129 (13)	0.0187 (14)
C18	0.0513 (15)	0.0550 (16)	0.0717 (16)	0.0093 (12)	0.0079 (12)	0.0117 (13)
C19	0.0487 (14)	0.0452 (14)	0.0657 (15)	0.0080 (11)	0.0193 (12)	0.0051 (11)

S1—C15	1.778 (2)	C7—H7	0.9300
S1—C14	1.791 (2)	C8—C9	1.358 (4)
S2—C15	1.665 (2)	C8—H8	0.9300
O1—C4	1.369 (2)	C9—C10	1.416 (3)
O1—C3	1.385 (2)	C9—H9	0.9300
O2—C3	1.206 (2)	C10—C11	1.421 (3)
O3—C17	1.422 (3)	C11—C12	1.353 (3)
O3—C18	1.432 (3)	C11—H11	0.9300
N1—C15	1.333 (3)	C12—C13	1.419 (3)
N1—C16	1.472 (3)	C12—H12	0.9300
N1—C19	1.477 (3)	C14—H14A	0.9700
C1—C2	1.344 (3)	C14—H14B	0.9700
C1—C13	1.452 (3)	C16—C17	1.482 (3)
C1—C14	1.511 (3)	C16—H16A	0.9700
C2—C3	1.436 (3)	C16—H16B	0.9700
C2—H2	0.9300	C17—H17A	0.9700
C4—C13	1.382 (3)	C17—H17B	0.9700
C4—C5	1.422 (3)	C18—C19	1.484 (3)
C5—C6	1.411 (3)	C18—H18A	0.9700
C5—C10	1.418 (3)	C18—H18B	0.9700
C6—C7	1.369 (3)	C19—H19A	0.9700
C6—H6	0.9300	C19—H19B	0.9700
C7—C8	1.392 (4)
C15—S1—C14	104.92 (11)	C11—C12—C13	121.5 (2)
C4—O1—C3	121.69 (16)	C11—C12—H12	119.3
C17—O3—C18	109.50 (18)	C13—C12—H12	119.3
C15—N1—C16	122.97 (19)	C4—C13—C12	117.56 (18)
C15—N1—C19	126.25 (18)	C4—C13—C1	117.83 (18)
C16—N1—C19	110.76 (18)	C12—C13—C1	124.60 (19)
C2—C1—C13	119.11 (19)	C1—C14—S1	116.03 (15)
C2—C1—C14	122.65 (18)	C1—C14—H14A	108.3
C13—C1—C14	118.24 (18)	S1—C14—H14A	108.3
C1—C2—C3	122.69 (19)	C1—C14—H14B	108.3
C1—C2—H2	118.7	S1—C14—H14B	108.3
C3—C2—H2	118.7	H14A—C14—H14B	107.4
O2—C3—O1	116.48 (19)	N1—C15—S2	124.86 (16)
O2—C3—C2	126.85 (19)	N1—C15—S1	112.65 (15)
O1—C3—C2	116.66 (18)	S2—C15—S1	122.47 (12)
O1—C4—C13	121.80 (17)	N1—C16—C17	109.4 (2)
O1—C4—C5	115.18 (18)	N1—C16—H16A	109.8
C13—C4—C5	123.01 (19)	C17—C16—H16A	109.8
C6—C5—C10	119.38 (19)	N1—C16—H16B	109.8
C6—C5—C4	123.2 (2)	C17—C16—H16B	109.8
C10—C5—C4	117.41 (19)	H16A—C16—H16B	108.2
C7—C6—C5	119.7 (2)	O3—C17—C16	111.5 (2)
C7—C6—H6	120.2	O3—C17—H17A	109.3
C5—C6—H6	120.2	C16—C17—H17A	109.3
C6—C7—C8	121.3 (2)	O3—C17—H17B	109.3
C6—C7—H7	119.4	C16—C17—H17B	109.3
C8—C7—H7	119.4	H17A—C17—H17B	108.0
C9—C8—C7	120.2 (2)	O3—C18—C19	111.5 (2)
C9—C8—H8	119.9	O3—C18—H18A	109.3
C7—C8—H8	119.9	C19—C18—H18A	109.3
C8—C9—C10	120.8 (2)	O3—C18—H18B	109.3
C8—C9—H9	119.6	C19—C18—H18B	109.3
C10—C9—H9	119.6	H18A—C18—H18B	108.0
C9—C10—C5	118.6 (2)	N1—C19—C18	110.0 (2)
C9—C10—C11	122.2 (2)	N1—C19—H19A	109.7
C5—C10—C11	119.20 (19)	C18—C19—H19A	109.7
C12—C11—C10	121.2 (2)	N1—C19—H19B	109.7
C12—C11—H11	119.4	C18—C19—H19B	109.7
C10—C11—H11	119.4	H19A—C19—H19B	108.2
C13—C1—C2—C3	−2.1 (3)	C5—C4—C13—C12	3.8 (3)
C14—C1—C2—C3	178.4 (2)	O1—C4—C13—C1	4.1 (3)
C4—O1—C3—O2	−176.30 (18)	C5—C4—C13—C1	−175.22 (18)
C4—O1—C3—C2	3.2 (3)	C11—C12—C13—C4	−2.0 (3)
C1—C2—C3—O2	−179.9 (2)	C11—C12—C13—C1	177.0 (2)
C1—C2—C3—O1	0.7 (3)	C2—C1—C13—C4	−0.2 (3)
C3—O1—C4—C13	−5.7 (3)	C14—C1—C13—C4	179.26 (19)
C3—O1—C4—C5	173.65 (17)	C2—C1—C13—C12	−179.2 (2)
O1—C4—C5—C6	−2.7 (3)	C14—C1—C13—C12	0.3 (3)
C13—C4—C5—C6	176.6 (2)	C2—C1—C14—S1	27.7 (3)
O1—C4—C5—C10	178.51 (17)	C13—C1—C14—S1	−151.80 (16)
C13—C4—C5—C10	−2.2 (3)	C15—S1—C14—C1	−92.49 (18)
C10—C5—C6—C7	1.0 (3)	C16—N1—C15—S2	1.3 (3)
C4—C5—C6—C7	−177.8 (2)	C19—N1—C15—S2	−177.02 (18)
C5—C6—C7—C8	−1.3 (4)	C16—N1—C15—S1	179.49 (18)
C6—C7—C8—C9	0.7 (4)	C19—N1—C15—S1	1.2 (3)
C7—C8—C9—C10	0.2 (4)	C14—S1—C15—N1	177.39 (16)
C8—C9—C10—C5	−0.4 (3)	C14—S1—C15—S2	−4.34 (16)
C8—C9—C10—C11	179.6 (2)	C15—N1—C16—C17	126.5 (2)
C6—C5—C10—C9	−0.1 (3)	C19—N1—C16—C17	−55.0 (3)
C4—C5—C10—C9	178.67 (19)	C18—O3—C17—C16	−60.7 (3)
C6—C5—C10—C11	179.8 (2)	N1—C16—C17—O3	58.7 (3)
C4—C5—C10—C11	−1.4 (3)	C17—O3—C18—C19	59.6 (3)
C9—C10—C11—C12	−176.9 (2)	C15—N1—C19—C18	−127.2 (2)
C5—C10—C11—C12	3.2 (3)	C16—N1—C19—C18	54.3 (3)
C10—C11—C12—C13	−1.5 (3)	O3—C18—C19—N1	−56.7 (3)
O1—C4—C13—C12	−176.88 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O3i	0.93	2.42	3.346 (3)	173
C18—H18A···O2ii	0.97	2.56	3.466 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O3i	0.93	2.42	3.346 (3)	173
C18—H18A⋯O2ii	0.97	2.56	3.466 (3)	155

Symmetry codes: (i) ; (ii) .