Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680704932X/hb2549sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680704932X/hb2549Isup2.hkl |
CCDC reference: 667342
The title compound was synthesized according to the literature method (She & Huang, 2007). Colourless blocks of (I) were obtained by slow evaporation of the dichloromethane solution at 283 K.
The positions of H12 and H14 were freely refined with Uiso(H) = 1.2Ueq(C). The other H atoms were positioned geometrically, with C—H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
Quinazolinone is a naturally occurring alkaloid as well as a core structural subunit in a growing class of bioactive natural products and synthetic compounds (Liu et al., 2006). Furthermore, dithiocarbamate derivatives are found to possess pharmacological activities and generally form an essential part of the molecular structure of important drugs (Cao et al., 2005). We report herein the crystal structure of the title dithiocarbamate derivative, (I).
In the molecule of (I), (Fig. 1) the bond lengths and angles are generally within normal ranges (Allen et al., 1987) and are in accordance with the corresponding values in similar compounds (She & Huang, 2007). Rings A (N1/N2/C1/C6—C8) and B (C1—C6) are, of course, planar and they are also almost coplanar with a dihedral angle of A/B = 3.60 (3)°.
In the crystal, a weak intermolecular C—H···O hydrogen bond (Table 1, Fig. 2) link the molecules into chains along the c axis.
For related literature, see: Liu et al. (2006); Cao et al. (2005). For bond-length data, see: Allen et al. (1987). For related structures, see: She & Huang (2007); Jiang (2007).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Bruker, 2001).
C16H21N3OS2 | F(000) = 712 |
Mr = 335.48 | Dx = 1.323 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3183 reflections |
a = 12.9585 (12) Å | θ = 2.3–23.8° |
b = 8.8470 (8) Å | µ = 0.32 mm−1 |
c = 14.9378 (15) Å | T = 292 K |
β = 100.422 (2)° | Block, colorless |
V = 1684.3 (3) Å3 | 0.20 × 0.10 × 0.06 mm |
Z = 4 |
Bruker SMART 4K CCD diffractometer | 2740 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.033 |
Graphite monochromator | θmax = 27.0°, θmin = 1.9° |
φ and ω scans | h = −16→15 |
9077 measured reflections | k = −11→9 |
3615 independent reflections | l = −18→19 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.129 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0646P)2 + 0.1059P] where P = (Fo2 + 2Fc2)/3 |
3615 reflections | (Δ/σ)max < 0.001 |
209 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
C16H21N3OS2 | V = 1684.3 (3) Å3 |
Mr = 335.48 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 12.9585 (12) Å | µ = 0.32 mm−1 |
b = 8.8470 (8) Å | T = 292 K |
c = 14.9378 (15) Å | 0.20 × 0.10 × 0.06 mm |
β = 100.422 (2)° |
Bruker SMART 4K CCD diffractometer | 2740 reflections with I > 2σ(I) |
9077 measured reflections | Rint = 0.033 |
3615 independent reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.129 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.31 e Å−3 |
3615 reflections | Δρmin = −0.22 e Å−3 |
209 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. |
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 > σ(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 | 0.10518 (4) | 0.08161 (6) | 0.22859 (4) | 0.04484 (19) | |
S2 | −0.07121 (5) | 0.30153 (7) | 0.17179 (5) | 0.0584 (2) | |
N3 | −0.08186 (13) | 0.0036 (2) | 0.14073 (11) | 0.0388 (4) | |
N2 | 0.21525 (13) | 0.31472 (19) | 0.17370 (11) | 0.0401 (4) | |
C10 | −0.02751 (15) | 0.1253 (2) | 0.17468 (13) | 0.0368 (5) | |
O1 | 0.33747 (13) | 0.1290 (2) | 0.20134 (11) | 0.0583 (5) | |
C9 | 0.16744 (17) | 0.2629 (3) | 0.24957 (14) | 0.0444 (5) | |
H9A | 0.1157 | 0.3365 | 0.2608 | 0.053* | |
H9B | 0.2211 | 0.2568 | 0.3039 | 0.053* | |
C1 | 0.29368 (18) | 0.4198 (3) | 0.02963 (15) | 0.0469 (6) | |
C6 | 0.34002 (17) | 0.2922 (3) | 0.07510 (14) | 0.0444 (5) | |
N1 | 0.21223 (16) | 0.4984 (2) | 0.05789 (13) | 0.0503 (5) | |
C7 | 0.30154 (16) | 0.2364 (3) | 0.15455 (15) | 0.0437 (5) | |
C14 | −0.03619 (17) | −0.1516 (3) | 0.14633 (15) | 0.0448 (5) | |
H14 | 0.0382 (19) | −0.142 (3) | 0.1735 (15) | 0.054* | |
C8 | 0.17786 (18) | 0.4423 (2) | 0.12571 (15) | 0.0450 (5) | |
H8 | 0.1223 | 0.4924 | 0.1444 | 0.054* | |
C12 | −0.19555 (16) | 0.0091 (3) | 0.09710 (16) | 0.0474 (6) | |
H12 | −0.2154 (18) | −0.096 (3) | 0.0815 (16) | 0.057* | |
C5 | 0.42100 (19) | 0.2173 (3) | 0.04318 (18) | 0.0596 (7) | |
H5 | 0.4525 | 0.1331 | 0.0740 | 0.071* | |
C15 | −0.0415 (2) | −0.2205 (3) | 0.05282 (18) | 0.0653 (7) | |
H15A | −0.1134 | −0.2398 | 0.0262 | 0.098* | |
H15B | −0.0029 | −0.3137 | 0.0581 | 0.098* | |
H15C | −0.0116 | −0.1516 | 0.0149 | 0.098* | |
C2 | 0.3287 (2) | 0.4689 (3) | −0.04888 (17) | 0.0630 (7) | |
H2 | 0.2981 | 0.5531 | −0.0803 | 0.076* | |
C11 | −0.21454 (19) | 0.0946 (3) | 0.00728 (16) | 0.0607 (7) | |
H11A | −0.1963 | 0.1991 | 0.0182 | 0.091* | |
H11B | −0.2872 | 0.0869 | −0.0203 | 0.091* | |
H11C | −0.1720 | 0.0519 | −0.0327 | 0.091* | |
C3 | 0.4073 (2) | 0.3937 (4) | −0.07935 (19) | 0.0735 (8) | |
H3 | 0.4300 | 0.4272 | −0.1315 | 0.088* | |
C4 | 0.4538 (2) | 0.2679 (4) | −0.0335 (2) | 0.0732 (8) | |
H4 | 0.5076 | 0.2178 | −0.0550 | 0.088* | |
C16 | −0.0861 (2) | −0.2510 (3) | 0.20894 (19) | 0.0701 (8) | |
H16A | −0.0771 | −0.2055 | 0.2682 | 0.105* | |
H16B | −0.0533 | −0.3486 | 0.2135 | 0.105* | |
H16C | −0.1596 | −0.2618 | 0.1849 | 0.105* | |
C13 | −0.26576 (19) | 0.0594 (4) | 0.1623 (2) | 0.0725 (8) | |
H13A | −0.2492 | 0.0023 | 0.2177 | 0.109* | |
H13B | −0.3378 | 0.0428 | 0.1350 | 0.109* | |
H13C | −0.2548 | 0.1650 | 0.1755 | 0.109* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0407 (3) | 0.0363 (3) | 0.0540 (3) | −0.0030 (2) | −0.0009 (2) | 0.0056 (2) |
S2 | 0.0552 (4) | 0.0392 (4) | 0.0779 (5) | 0.0094 (3) | 0.0045 (3) | −0.0070 (3) |
N3 | 0.0366 (9) | 0.0397 (11) | 0.0398 (9) | −0.0017 (8) | 0.0056 (7) | −0.0011 (8) |
N2 | 0.0446 (10) | 0.0334 (10) | 0.0410 (9) | −0.0048 (8) | 0.0040 (7) | −0.0009 (7) |
C10 | 0.0390 (10) | 0.0387 (12) | 0.0337 (10) | 0.0014 (9) | 0.0094 (8) | 0.0010 (9) |
O1 | 0.0542 (10) | 0.0527 (11) | 0.0664 (10) | 0.0071 (8) | 0.0069 (8) | 0.0199 (9) |
C9 | 0.0506 (12) | 0.0410 (13) | 0.0396 (11) | −0.0099 (10) | 0.0026 (9) | −0.0034 (9) |
C1 | 0.0521 (13) | 0.0430 (14) | 0.0428 (12) | −0.0119 (11) | 0.0010 (10) | −0.0012 (10) |
C6 | 0.0432 (12) | 0.0413 (13) | 0.0473 (12) | −0.0065 (10) | 0.0047 (9) | −0.0018 (10) |
N1 | 0.0608 (12) | 0.0395 (11) | 0.0491 (11) | −0.0002 (9) | 0.0063 (9) | 0.0029 (9) |
C7 | 0.0418 (12) | 0.0384 (13) | 0.0478 (12) | −0.0056 (10) | −0.0004 (9) | 0.0008 (10) |
C14 | 0.0417 (12) | 0.0342 (13) | 0.0574 (13) | −0.0005 (10) | 0.0061 (10) | −0.0009 (10) |
C8 | 0.0511 (12) | 0.0326 (12) | 0.0487 (12) | 0.0007 (10) | 0.0024 (10) | −0.0043 (10) |
C12 | 0.0364 (11) | 0.0519 (15) | 0.0532 (13) | 0.0005 (10) | 0.0061 (9) | −0.0017 (11) |
C5 | 0.0516 (14) | 0.0583 (17) | 0.0687 (16) | −0.0011 (12) | 0.0106 (12) | −0.0026 (13) |
C15 | 0.0670 (16) | 0.0579 (17) | 0.0738 (17) | 0.0029 (13) | 0.0198 (13) | −0.0197 (13) |
C2 | 0.0730 (18) | 0.0618 (18) | 0.0541 (15) | −0.0097 (14) | 0.0110 (13) | 0.0089 (13) |
C11 | 0.0556 (14) | 0.0644 (18) | 0.0564 (14) | 0.0026 (13) | −0.0052 (11) | 0.0039 (12) |
C3 | 0.079 (2) | 0.087 (2) | 0.0579 (16) | −0.0156 (18) | 0.0217 (14) | 0.0035 (15) |
C4 | 0.0619 (17) | 0.088 (2) | 0.0757 (19) | −0.0038 (16) | 0.0275 (15) | −0.0124 (17) |
C16 | 0.085 (2) | 0.0526 (17) | 0.0726 (17) | −0.0013 (14) | 0.0151 (15) | 0.0173 (14) |
C13 | 0.0442 (14) | 0.094 (2) | 0.0831 (19) | 0.0049 (15) | 0.0225 (13) | −0.0084 (16) |
S1—C9 | 1.798 (2) | C12—C13 | 1.515 (3) |
S1—C10 | 1.804 (2) | C12—C11 | 1.521 (3) |
S2—C10 | 1.657 (2) | C12—H12 | 0.98 (2) |
N3—C10 | 1.335 (3) | C5—C4 | 1.368 (4) |
N3—C14 | 1.492 (3) | C5—H5 | 0.9300 |
N3—C12 | 1.500 (3) | C15—H15A | 0.9600 |
N2—C8 | 1.377 (3) | C15—H15B | 0.9600 |
N2—C7 | 1.389 (3) | C15—H15C | 0.9600 |
N2—C9 | 1.460 (3) | C2—C3 | 1.362 (4) |
O1—C7 | 1.221 (3) | C2—H2 | 0.9300 |
C9—H9A | 0.9700 | C11—H11A | 0.9600 |
C9—H9B | 0.9700 | C11—H11B | 0.9600 |
C1—N1 | 1.392 (3) | C11—H11C | 0.9600 |
C1—C6 | 1.396 (3) | C3—C4 | 1.387 (4) |
C1—C2 | 1.401 (3) | C3—H3 | 0.9300 |
C6—C5 | 1.396 (3) | C4—H4 | 0.9300 |
C6—C7 | 1.454 (3) | C16—H16A | 0.9600 |
N1—C8 | 1.278 (3) | C16—H16B | 0.9600 |
C14—C16 | 1.511 (3) | C16—H16C | 0.9600 |
C14—C15 | 1.514 (3) | C13—H13A | 0.9600 |
C14—H14 | 0.98 (2) | C13—H13B | 0.9600 |
C8—H8 | 0.9300 | C13—H13C | 0.9600 |
C9—S1—C10 | 104.37 (10) | C13—C12—H12 | 105.5 (14) |
C10—N3—C14 | 122.98 (17) | C11—C12—H12 | 105.5 (14) |
C10—N3—C12 | 123.22 (18) | C4—C5—C6 | 119.8 (3) |
C14—N3—C12 | 113.76 (17) | C4—C5—H5 | 120.1 |
C8—N2—C7 | 121.50 (19) | C6—C5—H5 | 120.1 |
C8—N2—C9 | 120.15 (19) | C14—C15—H15A | 109.5 |
C7—N2—C9 | 118.28 (18) | C14—C15—H15B | 109.5 |
N3—C10—S2 | 126.48 (16) | H15A—C15—H15B | 109.5 |
N3—C10—S1 | 113.05 (15) | C14—C15—H15C | 109.5 |
S2—C10—S1 | 120.47 (12) | H15A—C15—H15C | 109.5 |
N2—C9—S1 | 112.62 (14) | H15B—C15—H15C | 109.5 |
N2—C9—H9A | 109.1 | C3—C2—C1 | 120.3 (3) |
S1—C9—H9A | 109.1 | C3—C2—H2 | 119.9 |
N2—C9—H9B | 109.1 | C1—C2—H2 | 119.9 |
S1—C9—H9B | 109.1 | C12—C11—H11A | 109.5 |
H9A—C9—H9B | 107.8 | C12—C11—H11B | 109.5 |
N1—C1—C6 | 122.7 (2) | H11A—C11—H11B | 109.5 |
N1—C1—C2 | 118.5 (2) | C12—C11—H11C | 109.5 |
C6—C1—C2 | 118.8 (2) | H11A—C11—H11C | 109.5 |
C5—C6—C1 | 120.1 (2) | H11B—C11—H11C | 109.5 |
C5—C6—C7 | 120.5 (2) | C2—C3—C4 | 120.8 (3) |
C1—C6—C7 | 119.4 (2) | C2—C3—H3 | 119.6 |
C8—N1—C1 | 116.0 (2) | C4—C3—H3 | 119.6 |
O1—C7—N2 | 120.6 (2) | C5—C4—C3 | 120.2 (3) |
O1—C7—C6 | 125.4 (2) | C5—C4—H4 | 119.9 |
N2—C7—C6 | 113.97 (19) | C3—C4—H4 | 119.9 |
N3—C14—C16 | 111.1 (2) | C14—C16—H16A | 109.5 |
N3—C14—C15 | 111.55 (19) | C14—C16—H16B | 109.5 |
C16—C14—C15 | 112.6 (2) | H16A—C16—H16B | 109.5 |
N3—C14—H14 | 107.1 (14) | C14—C16—H16C | 109.5 |
C16—C14—H14 | 107.1 (14) | H16A—C16—H16C | 109.5 |
C15—C14—H14 | 107.1 (13) | H16B—C16—H16C | 109.5 |
N1—C8—N2 | 126.2 (2) | C12—C13—H13A | 109.5 |
N1—C8—H8 | 116.9 | C12—C13—H13B | 109.5 |
N2—C8—H8 | 116.9 | H13A—C13—H13B | 109.5 |
N3—C12—C13 | 112.78 (19) | C12—C13—H13C | 109.5 |
N3—C12—C11 | 112.89 (19) | H13A—C13—H13C | 109.5 |
C13—C12—C11 | 113.6 (2) | H13B—C13—H13C | 109.5 |
N3—C12—H12 | 105.5 (14) | ||
C14—N3—C10—S2 | 180.00 (16) | C5—C6—C7—N2 | −174.88 (19) |
C12—N3—C10—S2 | −2.7 (3) | C1—C6—C7—N2 | 3.7 (3) |
C14—N3—C10—S1 | −0.7 (2) | C10—N3—C14—C16 | 112.0 (2) |
C12—N3—C10—S1 | 176.61 (15) | C12—N3—C14—C16 | −65.5 (2) |
C9—S1—C10—N3 | 170.00 (14) | C10—N3—C14—C15 | −121.5 (2) |
C9—S1—C10—S2 | −10.62 (15) | C12—N3—C14—C15 | 61.0 (2) |
C8—N2—C9—S1 | 115.45 (18) | C1—N1—C8—N2 | 1.4 (3) |
C7—N2—C9—S1 | −67.5 (2) | C7—N2—C8—N1 | 3.6 (3) |
C10—S1—C9—N2 | −89.67 (17) | C9—N2—C8—N1 | −179.47 (19) |
N1—C1—C6—C5 | 179.5 (2) | C10—N3—C12—C13 | −62.5 (3) |
C2—C1—C6—C5 | 1.1 (3) | C14—N3—C12—C13 | 115.0 (2) |
N1—C1—C6—C7 | 0.9 (3) | C10—N3—C12—C11 | 68.0 (3) |
C2—C1—C6—C7 | −177.5 (2) | C14—N3—C12—C11 | −114.5 (2) |
C6—C1—N1—C8 | −3.6 (3) | C1—C6—C5—C4 | −0.9 (4) |
C2—C1—N1—C8 | 174.8 (2) | C7—C6—C5—C4 | 177.7 (2) |
C8—N2—C7—O1 | 175.52 (19) | N1—C1—C2—C3 | −179.2 (2) |
C9—N2—C7—O1 | −1.5 (3) | C6—C1—C2—C3 | −0.7 (4) |
C8—N2—C7—C6 | −5.9 (3) | C1—C2—C3—C4 | 0.0 (4) |
C9—N2—C7—C6 | 177.09 (17) | C6—C5—C4—C3 | 0.3 (4) |
C5—C6—C7—O1 | 3.6 (3) | C2—C3—C4—C5 | 0.2 (4) |
C1—C6—C7—O1 | −177.8 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O1i | 0.93 | 2.57 | 3.103 (3) | 117 |
Symmetry code: (i) −x+1/2, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C16H21N3OS2 |
Mr | 335.48 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 292 |
a, b, c (Å) | 12.9585 (12), 8.8470 (8), 14.9378 (15) |
β (°) | 100.422 (2) |
V (Å3) | 1684.3 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.32 |
Crystal size (mm) | 0.20 × 0.10 × 0.06 |
Data collection | |
Diffractometer | Bruker SMART 4K CCD |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9077, 3615, 2740 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.129, 1.04 |
No. of reflections | 3615 |
No. of parameters | 209 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.31, −0.22 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT (Bruker, 2001, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXTL (Bruker, 2001).
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O1i | 0.93 | 2.57 | 3.103 (3) | 117 |
Symmetry code: (i) −x+1/2, y+1/2, −z+1/2. |
Quinazolinone is a naturally occurring alkaloid as well as a core structural subunit in a growing class of bioactive natural products and synthetic compounds (Liu et al., 2006). Furthermore, dithiocarbamate derivatives are found to possess pharmacological activities and generally form an essential part of the molecular structure of important drugs (Cao et al., 2005). We report herein the crystal structure of the title dithiocarbamate derivative, (I).
In the molecule of (I), (Fig. 1) the bond lengths and angles are generally within normal ranges (Allen et al., 1987) and are in accordance with the corresponding values in similar compounds (She & Huang, 2007). Rings A (N1/N2/C1/C6—C8) and B (C1—C6) are, of course, planar and they are also almost coplanar with a dihedral angle of A/B = 3.60 (3)°.
In the crystal, a weak intermolecular C—H···O hydrogen bond (Table 1, Fig. 2) link the molecules into chains along the c axis.