organic compounds
(6-Bromo-2-oxo-2H-chromen-4-yl)methyl diethylcarbamodithioate
aDepartment of Physics, Sri D Devaraja Urs Govt. First Grade College, Hunsur-571105, Mysore District, Karnataka, India, bDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore-570005, Karnataka, India, and cDepartment of Chemistry, Karnatak University's Karnatak Science College, Dharwad, Karnataka 580001, India
*Correspondence e-mail: devarajegowda@yahoo.com
In the title compound, C15H16BrNO2S2, the 2H-chromene ring system is nearly planar, with a maximum deviation of 0.0182 (22) Å. In the crystal, π–π interactions between pyran and benzene rings of chromene [shortest centroid–centroid distance = 3.7588 (14) Å] occur.
CCDC reference: 1445314
Structure description
Coumarin derivatives are an interesting class of heterocyclic system since the coumarin ring is an essential core moiety in a variety of natural and synthetic biologically active compounds. Coumarin and its derivatives are a group of et al., 2010; Sato et al., 2008; Singh et al., 2011). A series of dithiocarbamate compounds have been synthesized and found to possess in vitro and in vivo antitumor activity (Li et al., 2004; Guo et al., 2004). In an effort to look for the possible non-classical antifolates acting as antitumor agents, we were interested in the incorporation of the dithiocarbamate moiety with coumarin. Herein we report the synthesis, and structural characterization of (6-bromo-2-oxo-2H-chromen-4-yl)methyl diethylcarbamodithioate.
derived from Alternately stated, a coumarin ring system is formed by the fusion of benzene and 1,2-pyrone ring. The structure of benzopyrone has many advantages including high fluorescence large excellent light stability, and low toxicity (ZhouThe H-chromen-4-yl)methyl diethylcarbamodithioate is shown in Fig. 1. The 2H-chromene ring system (O4/C7–C15) is nearly planar, with a maximum deviation of 0.018 (2) Å for atom C13. In the crystal, π–π interactions between pyran (O4/C9/C10/C13–C15) and benzene rings of chromene [shortest centroid–centroid distance = 3.7588 (14) Å] occur.
of (6-bromo-2-oxo-2Synthesis and crystallization
All the chemicals used were of analytical reagent grade and were used directly without further purification. The title compound was synthesized according to the reported method (Kumar et al., 2012). The compound was recrystallized from an ethanol–chloroform mixture (v/v = 2/1) by slow evaporation at room temperature. Yield = 72%, m.p. 401–403 K; IR (KBr, cm−1): 985, 1141, 1201, 1410, 1492, and 1730. GCMS: m/e: 386. 1H NMR (400 MHz, CDCl3, δ, p.p.m): 7.74 (s, 1H, Ar—H), 7.51 (dd, 1H, Ar—H), 7.31 (t, 1H, Ar—H), 6.62 (s, 1H, Ar—H), 4.72 (s, 2H, CH2), 4.07 (q, 2H, CH2), 3.80 (q, 2H, CH2), 1.34 (q, 6H, CH3). Elemental analysis for C15H16BrNO2S2: C, 46.63; H, 4.17; N, 3.63 (calculated); C, 46.67; H, 4.12; N, 3.68(found).
Refinement
Crystal data, data collection and structure .
details are summarized in Table 1Structural data
CCDC reference: 1445314
10.1107/S2414314616000158/bv4001sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616000158/bv4001Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616000158/bv4001Isup3.cml
All the chemicals used were of analytical reagent grade and were used directly without further purification. The title compound was synthesized according to the reported method (Kumar et al., 2012). The compound was recrystallized from an ethanol–chloroform mixture (v/v = 2/1) by slow evaporation at room temperature. Yield = 72%, m.p. 401–403 K; IR (KBr, cm−1): 985, 1141, 1201, 1410, 1492, and 1730. GCMS: m/e: 386. 1H NMR (400 MHz, CDCl3, δ, p.p.m): 7.74 (s, 1H, Ar—H), 7.51 (dd, 1H, Ar—H), 7.31 (t, 1H, Ar—H), 6.62 (s, 1H, Ar—H), 4.72 (s, 2H, CH2), 4.07 (q, 2H, CH2), 3.80 (q, 2H, CH2), 1.34 (q, 6H, CH3). Elemental analysis for C15H16BrNO2S2: C, 46.63; H, 4.17; N, 3.63 (calculated); C, 46.67; H, 4.12; N, 3.68(found).
Coumarin derivatives are an interesting class of heterocyclic system since the coumarin ring is an essential core moiety in a variety of natural and synthetic biologically active compounds. Coumarin and its derivatives are a group of
derived from Alternately stated, a coumarin ring system is formed by the fusion of benzene and 1,2-pyrone ring. The structure of benzopyrone has many advantages including high fluorescence large excellent light stability, and low toxicity (Zhou et al., 2010; Sato et al., 2008; Singh et al., 2011). A series of dithiocarbamate compounds have been synthesized and found to possess in vitro and in vivo antitumor activity (Li et al., 2004; Guo et al., 2004). In an effort to look for the possible non-classical antifolates acting as antitumor agents, we were interested in the incorporation of the dithiocarbamate moiety with coumarin. Herein we report the synthesis, and structural characterization of (6-bromo-2-oxo-2H-chromen-4-yl)methyl diethylcarbamodithioate.The π–π interactions between pyran (O4/C9/C10/C13–C15) and benzene rings of chromene [shortest centroid–centroid distance = 3.7588 (14) Å] occur.
of (6-bromo-2-oxo-2H-chromen-4-yl)methyl diethylcarbamodithioate is shown in Fig. 1. The 2H-chromene ring system (O4/C7–C15) is nearly planar, with a maximum deviation of 0.018 (2) Å for atom C13. In the crystal,Data collection: SMART (Bruker, 2001); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2014/7.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. |
C15H16BrNO2S2 | Dx = 1.612 Mg m−3 |
Mr = 386.32 | Melting point: 401 K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 7.8958 (2) Å | Cell parameters from 2806 reflections |
b = 8.0536 (2) Å | θ = 2.8–25.0° |
c = 25.2735 (8) Å | µ = 2.85 mm−1 |
β = 97.909 (2)° | T = 296 K |
V = 1591.84 (8) Å3 | Plate, colourless |
Z = 4 | 0.24 × 0.20 × 0.12 mm |
F(000) = 784 |
Bruker SMART CCD area-detector diffractometer | 2806 independent reflections |
Radiation source: fine-focus sealed tube | 2419 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ω and φ scans | θmax = 25.0°, θmin = 2.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2007) | h = −9→9 |
Tmin = 0.770, Tmax = 1.000 | k = −9→9 |
12640 measured reflections | l = −30→28 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.030 | w = 1/[σ2(Fo2) + (0.0341P)2 + 0.9395P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.074 | (Δ/σ)max = 0.003 |
S = 1.04 | Δρmax = 0.62 e Å−3 |
2806 reflections | Δρmin = −0.44 e Å−3 |
191 parameters | Extinction correction: SHELXL2014/7 (Sheldrick 2015, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0078 (6) |
C15H16BrNO2S2 | V = 1591.84 (8) Å3 |
Mr = 386.32 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.8958 (2) Å | µ = 2.85 mm−1 |
b = 8.0536 (2) Å | T = 296 K |
c = 25.2735 (8) Å | 0.24 × 0.20 × 0.12 mm |
β = 97.909 (2)° |
Bruker SMART CCD area-detector diffractometer | 2806 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2007) | 2419 reflections with I > 2σ(I) |
Tmin = 0.770, Tmax = 1.000 | Rint = 0.033 |
12640 measured reflections |
R[F2 > 2σ(F2)] = 0.030 | 0 restraints |
wR(F2) = 0.074 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.62 e Å−3 |
2806 reflections | Δρmin = −0.44 e Å−3 |
191 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.59128 (4) | 1.00761 (4) | 1.10054 (2) | 0.05696 (14) | |
S2 | 0.97175 (8) | 0.75097 (8) | 0.86560 (2) | 0.03566 (17) | |
S3 | 0.60724 (8) | 0.65728 (8) | 0.82431 (3) | 0.03919 (18) | |
O4 | 0.7447 (2) | 0.3444 (2) | 1.01068 (7) | 0.0385 (4) | |
O5 | 0.8515 (3) | 0.1807 (2) | 0.95411 (8) | 0.0511 (5) | |
N6 | 0.8656 (2) | 0.6584 (2) | 0.76765 (8) | 0.0327 (4) | |
C7 | 0.6395 (3) | 0.8010 (3) | 1.06954 (10) | 0.0366 (6) | |
C8 | 0.7109 (3) | 0.7968 (3) | 1.02306 (10) | 0.0336 (5) | |
H8 | 0.7347 | 0.8951 | 1.0062 | 0.040* | |
C9 | 0.7477 (3) | 0.6432 (3) | 1.00118 (9) | 0.0306 (5) | |
C10 | 0.7105 (3) | 0.5005 (3) | 1.02818 (10) | 0.0324 (5) | |
C11 | 0.6357 (3) | 0.5063 (3) | 1.07453 (11) | 0.0409 (6) | |
H11 | 0.6103 | 0.4087 | 1.0915 | 0.049* | |
C12 | 0.5995 (3) | 0.6573 (3) | 1.09518 (11) | 0.0430 (6) | |
H12 | 0.5485 | 0.6632 | 1.1262 | 0.052* | |
C13 | 0.8253 (3) | 0.6230 (3) | 0.95250 (9) | 0.0291 (5) | |
C14 | 0.8597 (3) | 0.4683 (3) | 0.93707 (10) | 0.0332 (5) | |
H14 | 0.9110 | 0.4555 | 0.9063 | 0.040* | |
C15 | 0.8213 (3) | 0.3214 (3) | 0.96566 (10) | 0.0362 (6) | |
C16 | 0.8615 (3) | 0.7774 (3) | 0.92238 (10) | 0.0340 (5) | |
H16A | 0.9283 | 0.8521 | 0.9472 | 0.041* | |
H16B | 0.7534 | 0.8318 | 0.9105 | 0.041* | |
C17 | 0.8095 (3) | 0.6840 (3) | 0.81439 (9) | 0.0285 (5) | |
C18 | 1.0413 (3) | 0.6957 (4) | 0.75752 (11) | 0.0465 (7) | |
H18A | 1.0886 | 0.7822 | 0.7819 | 0.056* | |
H18B | 1.0373 | 0.7380 | 0.7214 | 0.056* | |
C19 | 1.1578 (4) | 0.5469 (5) | 0.76417 (16) | 0.0681 (9) | |
H19A | 1.2698 | 0.5783 | 0.7571 | 0.102* | |
H19B | 1.1645 | 0.5058 | 0.8001 | 0.102* | |
H19C | 1.1132 | 0.4616 | 0.7396 | 0.102* | |
C20 | 0.7533 (3) | 0.5899 (3) | 0.72156 (10) | 0.0406 (6) | |
H20A | 0.6700 | 0.5172 | 0.7344 | 0.049* | |
H20B | 0.8214 | 0.5234 | 0.7004 | 0.049* | |
C21 | 0.6610 (5) | 0.7204 (4) | 0.68662 (12) | 0.0607 (8) | |
H21A | 0.5900 | 0.6684 | 0.6574 | 0.091* | |
H21B | 0.5911 | 0.7851 | 0.7070 | 0.091* | |
H21C | 0.7426 | 0.7914 | 0.6730 | 0.091* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0733 (2) | 0.04765 (19) | 0.0528 (2) | 0.00713 (14) | 0.01885 (16) | −0.01305 (14) |
S2 | 0.0369 (3) | 0.0427 (4) | 0.0276 (3) | −0.0064 (3) | 0.0053 (2) | 0.0020 (3) |
S3 | 0.0343 (3) | 0.0448 (4) | 0.0391 (4) | −0.0033 (3) | 0.0073 (3) | 0.0049 (3) |
O4 | 0.0511 (10) | 0.0296 (9) | 0.0359 (10) | −0.0034 (7) | 0.0102 (8) | 0.0035 (7) |
O5 | 0.0772 (13) | 0.0281 (10) | 0.0493 (12) | 0.0013 (9) | 0.0127 (10) | −0.0027 (8) |
N6 | 0.0408 (11) | 0.0318 (10) | 0.0262 (11) | −0.0029 (8) | 0.0070 (8) | 0.0011 (8) |
C7 | 0.0394 (13) | 0.0387 (13) | 0.0318 (14) | 0.0032 (10) | 0.0054 (10) | −0.0051 (11) |
C8 | 0.0378 (13) | 0.0321 (13) | 0.0309 (14) | −0.0005 (10) | 0.0045 (10) | 0.0021 (10) |
C9 | 0.0301 (11) | 0.0329 (12) | 0.0278 (13) | −0.0012 (9) | 0.0006 (9) | 0.0020 (10) |
C10 | 0.0349 (12) | 0.0314 (12) | 0.0304 (13) | −0.0017 (9) | 0.0024 (10) | 0.0013 (10) |
C11 | 0.0472 (15) | 0.0410 (15) | 0.0367 (15) | −0.0059 (11) | 0.0137 (12) | 0.0087 (12) |
C12 | 0.0481 (15) | 0.0519 (16) | 0.0315 (14) | 0.0010 (12) | 0.0147 (12) | 0.0030 (12) |
C13 | 0.0314 (11) | 0.0313 (12) | 0.0239 (12) | −0.0020 (9) | 0.0007 (9) | 0.0003 (10) |
C14 | 0.0412 (13) | 0.0324 (13) | 0.0252 (12) | −0.0011 (10) | 0.0019 (10) | 0.0007 (10) |
C15 | 0.0429 (14) | 0.0326 (14) | 0.0317 (14) | −0.0018 (10) | −0.0001 (11) | −0.0008 (11) |
C16 | 0.0465 (14) | 0.0293 (12) | 0.0269 (13) | −0.0020 (10) | 0.0075 (10) | 0.0012 (10) |
C17 | 0.0402 (13) | 0.0214 (10) | 0.0237 (12) | 0.0005 (9) | 0.0042 (10) | 0.0060 (9) |
C18 | 0.0487 (15) | 0.0560 (17) | 0.0384 (16) | −0.0092 (13) | 0.0190 (12) | −0.0017 (13) |
C19 | 0.0454 (17) | 0.084 (2) | 0.076 (2) | 0.0058 (16) | 0.0126 (16) | −0.016 (2) |
C20 | 0.0592 (16) | 0.0317 (13) | 0.0305 (14) | −0.0043 (11) | 0.0043 (11) | −0.0047 (11) |
C21 | 0.090 (2) | 0.0470 (17) | 0.0392 (17) | −0.0020 (15) | −0.0134 (15) | 0.0049 (14) |
Br1—C7 | 1.900 (2) | C12—H12 | 0.9300 |
S2—C17 | 1.775 (2) | C13—C14 | 1.344 (3) |
S2—C16 | 1.791 (2) | C13—C16 | 1.506 (3) |
S3—C17 | 1.664 (2) | C14—C15 | 1.440 (3) |
O4—C10 | 1.371 (3) | C14—H14 | 0.9300 |
O4—C15 | 1.372 (3) | C16—H16A | 0.9700 |
O5—C15 | 1.203 (3) | C16—H16B | 0.9700 |
N6—C17 | 1.333 (3) | C18—C19 | 1.506 (4) |
N6—C20 | 1.471 (3) | C18—H18A | 0.9700 |
N6—C18 | 1.476 (3) | C18—H18B | 0.9700 |
C7—C8 | 1.372 (3) | C19—H19A | 0.9600 |
C7—C12 | 1.384 (4) | C19—H19B | 0.9600 |
C8—C9 | 1.402 (3) | C19—H19C | 0.9600 |
C8—H8 | 0.9300 | C20—C21 | 1.496 (4) |
C9—C10 | 1.389 (3) | C20—H20A | 0.9700 |
C9—C13 | 1.457 (3) | C20—H20B | 0.9700 |
C10—C11 | 1.383 (4) | C21—H21A | 0.9600 |
C11—C12 | 1.369 (4) | C21—H21B | 0.9600 |
C11—H11 | 0.9300 | C21—H21C | 0.9600 |
C17—S2—C16 | 103.82 (11) | C13—C16—H16A | 108.0 |
C10—O4—C15 | 121.33 (18) | S2—C16—H16A | 108.0 |
C17—N6—C20 | 121.4 (2) | C13—C16—H16B | 108.0 |
C17—N6—C18 | 123.9 (2) | S2—C16—H16B | 108.0 |
C20—N6—C18 | 114.7 (2) | H16A—C16—H16B | 107.3 |
C8—C7—C12 | 121.9 (2) | N6—C17—S3 | 123.80 (18) |
C8—C7—Br1 | 120.24 (19) | N6—C17—S2 | 113.48 (17) |
C12—C7—Br1 | 117.90 (19) | S3—C17—S2 | 122.72 (14) |
C7—C8—C9 | 119.4 (2) | N6—C18—C19 | 113.1 (2) |
C7—C8—H8 | 120.3 | N6—C18—H18A | 109.0 |
C9—C8—H8 | 120.3 | C19—C18—H18A | 109.0 |
C10—C9—C8 | 117.9 (2) | N6—C18—H18B | 109.0 |
C10—C9—C13 | 117.7 (2) | C19—C18—H18B | 109.0 |
C8—C9—C13 | 124.4 (2) | H18A—C18—H18B | 107.8 |
O4—C10—C11 | 115.5 (2) | C18—C19—H19A | 109.5 |
O4—C10—C9 | 122.4 (2) | C18—C19—H19B | 109.5 |
C11—C10—C9 | 122.1 (2) | H19A—C19—H19B | 109.5 |
C12—C11—C10 | 119.3 (2) | C18—C19—H19C | 109.5 |
C12—C11—H11 | 120.4 | H19A—C19—H19C | 109.5 |
C10—C11—H11 | 120.4 | H19B—C19—H19C | 109.5 |
C11—C12—C7 | 119.4 (2) | N6—C20—C21 | 113.3 (2) |
C11—C12—H12 | 120.3 | N6—C20—H20A | 108.9 |
C7—C12—H12 | 120.3 | C21—C20—H20A | 108.9 |
C14—C13—C9 | 118.3 (2) | N6—C20—H20B | 108.9 |
C14—C13—C16 | 124.0 (2) | C21—C20—H20B | 108.9 |
C9—C13—C16 | 117.8 (2) | H20A—C20—H20B | 107.7 |
C13—C14—C15 | 123.4 (2) | C20—C21—H21A | 109.5 |
C13—C14—H14 | 118.3 | C20—C21—H21B | 109.5 |
C15—C14—H14 | 118.3 | H21A—C21—H21B | 109.5 |
O5—C15—O4 | 117.0 (2) | C20—C21—H21C | 109.5 |
O5—C15—C14 | 126.2 (2) | H21A—C21—H21C | 109.5 |
O4—C15—C14 | 116.9 (2) | H21B—C21—H21C | 109.5 |
C13—C16—S2 | 116.99 (17) |
Experimental details
Crystal data | |
Chemical formula | C15H16BrNO2S2 |
Mr | 386.32 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 296 |
a, b, c (Å) | 7.8958 (2), 8.0536 (2), 25.2735 (8) |
β (°) | 97.909 (2) |
V (Å3) | 1591.84 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.85 |
Crystal size (mm) | 0.24 × 0.20 × 0.12 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2007) |
Tmin, Tmax | 0.770, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12640, 2806, 2419 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.030, 0.074, 1.04 |
No. of reflections | 2806 |
No. of parameters | 191 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.62, −0.44 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL2014/7 (Sheldrick, 2015), ORTEP-3 for Windows (Farrugia, 2012), SHELXL2014/7.
Acknowledgements
The authors thank to Universities Sophisticated Instrumental Centre, Karnatak University, Dharwad for CCD X-ray facilities, X-ray data collection.
References
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Coumarin derivatives are an interesting class of heterocyclic system since the coumarin ring is an essential core moiety in a variety of natural and synthetic biologically active compounds. Coumarin and its derivatives are a group of lactones derived from phenols. Alternately stated, a coumarin ring system is formed by the fusion of benzene and 1,2-pyrone ring. The structure of benzopyrone has many advantages including high fluorescence quantum yield, large Stokes shift, excellent light stability, and low toxicity [(Zhou et al., 2010); (Sato et al., 2008); (Singh et al., 2011)]. A series of dithiocarbamate compounds have been synthesized and found to possess in vitro and in vivo antitumor activity [(Li et al., 2004); (Guo et al., 2004)]. In an effort to look for the possible non-classical antifolates acting as antitumor agents, we were interested in the incorporation of the dithiocarbamate moiety with coumarin. Herein we report the synthesis, and structural characterization of (6-bromo-2-oxo-2H-chromen-4-yl)methyl diethylcarbamodithioate.
The asymmetric unit of (6-bromo-2-oxo-2H-chromen-4-yl)methyl diethylcarbamodithioate is shown in Fig. 1. The 2H-chromene ring systems (O4/C7–C15) is nearly planar, with a maximum deviation of 0.0182 (22) Å for atom C13. In the crystal structure, inversion-related C—H···Br hydrogen bonds form inversion dimers with an R2 2(7) ring motif. In addition, weak intramolecular C—H···O hydrogen bonds along with π–π interactions between pyran (O4/C9/C10/C13–C15) and benzene rings of chromene [shortest centroid–centroid distance = 3.7588 (14) Å], stabilize the crystal packing.