Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807036409/bh2124sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807036409/bh2124Isup2.hkl |
CCDC reference: 657870
Glycine (5 mmol) was refluxed in sulfuryl dichloride (10 ml) for 6 h., and then 2-phenyl-1,3-selenazole methanol was added to the solution. The mixture was refluxed for 4 h., sulfuryl dichloride was evaporated and the residue was washed with water. The residue was dissolved in ether, giving a yellow solution, which afforded yellow single crystals after 7 days.
All H atom were positioned geometrically and refined using a riding model. Constrained C—H bond lengths: 0.93 (aromatic CH) or 0.97 Å (methylene CH2). isotropic displacement parameters for H atoms: Uiso(H) = 1.2Ueq(carrier C).
Selenium-containing molecules are of considerable biochemical and pharmacological relevance. A prominent example is the antitumor and antiviral active C-glycosyl selenazole selenazofurin (Koketsu & Ishihara, 2003; Geisler et al., 2004). In order to prepare compounds with higher anticancer activity, we planed to synthesize some selenazole derivatives containing amino acids. By reacting 2-phenyl-1,3-selenazole methanol with glycine in sulfuryl dichloride, we unexpectedly obtained the title compound, (I), and obtained single crystals suitable for X-ray diffraction.
The asymmetric unit of (I) contains two independent molecules, quoted 1 and 2 for Se1 and Se2 containing molecules, respectively (Fig. 1). The dihedral angle between phenyl and selenazole rings are 7.25 (9) and 7.47 (9)° for molecules 1 and 2, respectively. The Se—C distances, 1.852 (4), 1.883 (3) Å as well as the bond angle C—Se—C, 83.79 (14) ° in molecule 1, are slightly different than corresponding bond lengths [1.851 (3) and 1.878 (3) Å] and angle [83.25 (13)°] in molecule 2. The N═C and N—C distances in molecule 1 are 1.282 (4) and 1.386 (4) Å; the corresponding distances in molecule 2 are 1.291 (3) and 1.372 (4) Å.
In the asymmetric unit, the dihedral angle between two neighboring phenyl rings is 65.79 (11)°, and angle between two neighboring selenazole rings is 51.12 (9)°. Furthermore, there are weak C—H···Se and C—H···Cl intramolecular hydrogen bonds, involving C6 and Se1, C16 and Se2, C1 and Cl2, C11 and Cl3, forming five-membered rings. Via hydrogen bond interactions, all the skeletal atoms in each independent molecule, except for chloromethyl Cl atoms, are approximately coplanar, with maximum deviations of -0.112 Å for C20 and 0.102 Å for C7.
For related literature, see: Koketsu & Ishihara, 2003; Geisler et al., 2004.
Data collection: APEX2 (Bruker, 2004); cell refinement: SMART (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXTL (Bruker, 2004); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Fig. 1. A view of the molecule of (I) showing the atom-labeling scheme, with displacement ellipsoids drawn at the 30% probability level. dashed lines represent intramolecular hydrogen bonds. |
C10H7Cl2NSe | Z = 4 |
Mr = 291.03 | F(000) = 568 |
Triclinic, P1 | Dx = 1.773 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.1640 (5) Å | Cell parameters from 5903 reflections |
b = 10.4050 (6) Å | θ = 1.6–27.7° |
c = 13.7225 (7) Å | µ = 3.89 mm−1 |
α = 76.264 (3)° | T = 296 K |
β = 74.357 (3)° | Block, yellow |
γ = 86.475 (3)° | 0.57 × 0.30 × 0.22 mm |
V = 1090.39 (11) Å3 |
Bruker APEX2 area-detector diffractometer | 5021 independent reflections |
Radiation source: fine-focus sealed tube | 3550 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
φ and ω scans | θmax = 27.7°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→10 |
Tmin = 0.256, Tmax = 0.423 | k = −13→13 |
17299 measured reflections | l = −17→17 |
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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.098 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0445P)2 + 0.4631P] where P = (Fo2 + 2Fc2)/3 |
5021 reflections | (Δ/σ)max = 0.001 |
253 parameters | Δρmax = 0.42 e Å−3 |
0 restraints | Δρmin = −0.48 e Å−3 |
C10H7Cl2NSe | γ = 86.475 (3)° |
Mr = 291.03 | V = 1090.39 (11) Å3 |
Triclinic, P1 | Z = 4 |
a = 8.1640 (5) Å | Mo Kα radiation |
b = 10.4050 (6) Å | µ = 3.89 mm−1 |
c = 13.7225 (7) Å | T = 296 K |
α = 76.264 (3)° | 0.57 × 0.30 × 0.22 mm |
β = 74.357 (3)° |
Bruker APEX2 area-detector diffractometer | 5021 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3550 reflections with I > 2σ(I) |
Tmin = 0.256, Tmax = 0.423 | Rint = 0.028 |
17299 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.098 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.42 e Å−3 |
5021 reflections | Δρmin = −0.48 e Å−3 |
253 parameters |
x | y | z | Uiso*/Ueq | ||
Se1 | 1.37993 (5) | 1.00206 (4) | −0.11871 (3) | 0.06946 (13) | |
Se2 | 0.72129 (4) | 0.96216 (3) | 0.65950 (2) | 0.06129 (12) | |
Cl1 | 1.2736 (2) | 1.44955 (11) | −0.02164 (11) | 0.1177 (5) | |
Cl2 | 1.43418 (18) | 1.27694 (13) | −0.27490 (8) | 0.1086 (4) | |
Cl3 | 0.56928 (17) | 0.69066 (11) | 0.79275 (8) | 0.1012 (4) | |
Cl4 | 0.70828 (12) | 0.54767 (9) | 0.52221 (9) | 0.0791 (3) | |
N1 | 1.1682 (3) | 1.1290 (2) | 0.01349 (19) | 0.0552 (6) | |
N2 | 0.6747 (3) | 0.8781 (2) | 0.49813 (19) | 0.0500 (6) | |
C1 | 1.1660 (6) | 1.3615 (3) | −0.0819 (3) | 0.0866 (12) | |
H1A | 1.0453 | 1.3592 | −0.0477 | 0.104* | |
H1B | 1.1811 | 1.4075 | −0.1540 | 0.104* | |
C2 | 1.2296 (4) | 1.2242 (3) | −0.0772 (3) | 0.0601 (8) | |
C3 | 1.3401 (4) | 1.1821 (3) | −0.1550 (3) | 0.0650 (8) | |
C4 | 1.2275 (3) | 1.0130 (3) | 0.0093 (2) | 0.0488 (6) | |
C5 | 1.1829 (4) | 0.8961 (3) | 0.0952 (2) | 0.0498 (7) | |
C6 | 1.2630 (5) | 0.7759 (3) | 0.0919 (3) | 0.0771 (10) | |
H6A | 1.3466 | 0.7661 | 0.0329 | 0.093* | |
C7 | 1.2180 (6) | 0.6693 (4) | 0.1774 (4) | 0.0937 (13) | |
H7A | 1.2740 | 0.5889 | 0.1760 | 0.112* | |
C8 | 1.0924 (6) | 0.6819 (4) | 0.2632 (3) | 0.0832 (11) | |
H8A | 1.0617 | 0.6098 | 0.3194 | 0.100* | |
C9 | 1.0126 (5) | 0.7990 (4) | 0.2667 (3) | 0.0712 (9) | |
H9A | 0.9269 | 0.8070 | 0.3254 | 0.085* | |
C10 | 1.0572 (4) | 0.9069 (3) | 0.1840 (2) | 0.0577 (7) | |
H10A | 1.0027 | 0.9874 | 0.1878 | 0.069* | |
C11 | 0.5462 (4) | 0.6569 (3) | 0.5694 (3) | 0.0686 (9) | |
H11A | 0.4769 | 0.6834 | 0.5207 | 0.082* | |
H11B | 0.4733 | 0.6107 | 0.6353 | 0.082* | |
C12 | 0.6184 (3) | 0.7770 (3) | 0.5839 (3) | 0.0543 (7) | |
C13 | 0.6302 (4) | 0.7979 (3) | 0.6745 (3) | 0.0599 (8) | |
C14 | 0.7312 (3) | 0.9791 (3) | 0.5186 (2) | 0.0455 (6) | |
C15 | 0.7991 (3) | 1.0989 (3) | 0.4403 (2) | 0.0464 (6) | |
C16 | 0.8770 (4) | 1.1978 (3) | 0.4642 (3) | 0.0589 (8) | |
H16A | 0.8828 | 1.1904 | 0.5320 | 0.071* | |
C17 | 0.9459 (4) | 1.3072 (3) | 0.3878 (3) | 0.0716 (10) | |
H17A | 0.9982 | 1.3731 | 0.4043 | 0.086* | |
C18 | 0.9374 (5) | 1.3189 (3) | 0.2881 (3) | 0.0776 (11) | |
H18A | 0.9855 | 1.3922 | 0.2367 | 0.093* | |
C19 | 0.8585 (5) | 1.2234 (4) | 0.2632 (3) | 0.0740 (10) | |
H19A | 0.8515 | 1.2328 | 0.1954 | 0.089* | |
C20 | 0.7894 (4) | 1.1132 (3) | 0.3388 (2) | 0.0581 (8) | |
H20A | 0.7362 | 1.0484 | 0.3217 | 0.070* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Se1 | 0.0758 (2) | 0.0742 (2) | 0.0559 (2) | −0.00109 (17) | −0.00420 (16) | −0.02466 (17) |
Se2 | 0.0703 (2) | 0.0623 (2) | 0.0538 (2) | 0.00479 (15) | −0.01144 (15) | −0.02474 (15) |
Cl1 | 0.1783 (13) | 0.0675 (7) | 0.1169 (10) | −0.0122 (7) | −0.0441 (9) | −0.0301 (6) |
Cl2 | 0.1377 (10) | 0.1113 (9) | 0.0589 (6) | −0.0308 (8) | −0.0132 (6) | 0.0084 (6) |
Cl3 | 0.1291 (9) | 0.0759 (6) | 0.0670 (6) | 0.0129 (6) | 0.0058 (6) | 0.0052 (5) |
Cl4 | 0.0805 (6) | 0.0569 (5) | 0.1084 (8) | 0.0072 (4) | −0.0265 (5) | −0.0352 (5) |
N1 | 0.0638 (15) | 0.0485 (14) | 0.0533 (15) | 0.0038 (12) | −0.0148 (12) | −0.0136 (12) |
N2 | 0.0474 (12) | 0.0482 (14) | 0.0561 (15) | 0.0012 (10) | −0.0112 (11) | −0.0185 (12) |
C1 | 0.117 (3) | 0.055 (2) | 0.088 (3) | 0.005 (2) | −0.040 (2) | −0.0034 (19) |
C2 | 0.073 (2) | 0.0517 (18) | 0.059 (2) | −0.0047 (15) | −0.0263 (16) | −0.0078 (15) |
C3 | 0.076 (2) | 0.070 (2) | 0.0488 (18) | −0.0167 (17) | −0.0182 (16) | −0.0062 (16) |
C4 | 0.0501 (15) | 0.0526 (17) | 0.0481 (16) | −0.0009 (13) | −0.0135 (12) | −0.0193 (13) |
C5 | 0.0538 (16) | 0.0471 (16) | 0.0545 (17) | −0.0025 (12) | −0.0197 (13) | −0.0160 (13) |
C6 | 0.089 (2) | 0.052 (2) | 0.085 (3) | 0.0110 (18) | −0.013 (2) | −0.0213 (19) |
C7 | 0.122 (4) | 0.045 (2) | 0.116 (4) | 0.012 (2) | −0.042 (3) | −0.014 (2) |
C8 | 0.113 (3) | 0.058 (2) | 0.078 (3) | −0.017 (2) | −0.035 (2) | 0.000 (2) |
C9 | 0.083 (2) | 0.073 (2) | 0.056 (2) | −0.0168 (19) | −0.0186 (17) | −0.0083 (17) |
C10 | 0.0669 (18) | 0.0546 (18) | 0.0531 (18) | −0.0008 (14) | −0.0164 (15) | −0.0142 (15) |
C11 | 0.0552 (17) | 0.0511 (18) | 0.096 (3) | −0.0055 (14) | −0.0069 (17) | −0.0230 (18) |
C12 | 0.0448 (15) | 0.0468 (17) | 0.067 (2) | 0.0047 (12) | −0.0049 (13) | −0.0179 (15) |
C13 | 0.0588 (18) | 0.0527 (18) | 0.0571 (19) | 0.0058 (14) | −0.0010 (14) | −0.0089 (15) |
C14 | 0.0391 (13) | 0.0483 (16) | 0.0517 (16) | 0.0072 (11) | −0.0091 (11) | −0.0217 (13) |
C15 | 0.0411 (13) | 0.0422 (15) | 0.0564 (17) | 0.0070 (11) | −0.0096 (12) | −0.0177 (13) |
C16 | 0.0584 (17) | 0.0489 (17) | 0.073 (2) | 0.0038 (14) | −0.0169 (15) | −0.0215 (16) |
C17 | 0.065 (2) | 0.0465 (19) | 0.103 (3) | −0.0019 (15) | −0.020 (2) | −0.0188 (19) |
C18 | 0.071 (2) | 0.0480 (19) | 0.097 (3) | 0.0032 (16) | −0.009 (2) | −0.0001 (19) |
C19 | 0.084 (2) | 0.064 (2) | 0.065 (2) | 0.0100 (18) | −0.0134 (18) | −0.0054 (18) |
C20 | 0.0585 (17) | 0.0553 (18) | 0.061 (2) | 0.0048 (14) | −0.0126 (15) | −0.0198 (15) |
Se1—C3 | 1.852 (4) | C7—H7A | 0.9300 |
Se1—C4 | 1.883 (3) | C8—C9 | 1.351 (5) |
Se2—C13 | 1.851 (3) | C8—H8A | 0.9300 |
Se2—C14 | 1.878 (3) | C9—C10 | 1.379 (5) |
Cl1—C1 | 1.773 (4) | C9—H9A | 0.9300 |
Cl2—C3 | 1.706 (3) | C10—H10A | 0.9300 |
Cl3—C13 | 1.703 (3) | C11—C12 | 1.490 (4) |
Cl4—C11 | 1.779 (3) | C11—H11A | 0.9700 |
N1—C4 | 1.282 (4) | C11—H11B | 0.9700 |
N1—C2 | 1.386 (4) | C12—C13 | 1.341 (4) |
N2—C14 | 1.291 (3) | C14—C15 | 1.464 (4) |
N2—C12 | 1.372 (4) | C15—C16 | 1.386 (4) |
C1—C2 | 1.482 (5) | C15—C20 | 1.389 (4) |
C1—H1A | 0.9700 | C16—C17 | 1.380 (5) |
C1—H1B | 0.9700 | C16—H16A | 0.9300 |
C2—C3 | 1.342 (5) | C17—C18 | 1.365 (6) |
C4—C5 | 1.464 (4) | C17—H17A | 0.9300 |
C5—C6 | 1.380 (4) | C18—C19 | 1.371 (5) |
C5—C10 | 1.388 (4) | C18—H18A | 0.9300 |
C6—C7 | 1.393 (6) | C19—C20 | 1.381 (5) |
C6—H6A | 0.9300 | C19—H19A | 0.9300 |
C7—C8 | 1.364 (6) | C20—H20A | 0.9300 |
C3—Se1—C4 | 83.79 (14) | C9—C10—H10A | 119.8 |
C13—Se2—C14 | 83.25 (13) | C5—C10—H10A | 119.8 |
C4—N1—C2 | 113.8 (3) | C12—C11—Cl4 | 111.8 (2) |
C14—N2—C12 | 113.7 (3) | C12—C11—H11A | 109.3 |
C2—C1—Cl1 | 112.0 (3) | Cl4—C11—H11A | 109.3 |
C2—C1—H1A | 109.2 | C12—C11—H11B | 109.3 |
Cl1—C1—H1A | 109.2 | Cl4—C11—H11B | 109.3 |
C2—C1—H1B | 109.2 | H11A—C11—H11B | 107.9 |
Cl1—C1—H1B | 109.2 | C13—C12—N2 | 115.9 (3) |
H1A—C1—H1B | 107.9 | C13—C12—C11 | 125.9 (3) |
C3—C2—N1 | 116.1 (3) | N2—C12—C11 | 118.1 (3) |
C3—C2—C1 | 125.5 (3) | C12—C13—Cl3 | 126.1 (3) |
N1—C2—C1 | 118.3 (3) | C12—C13—Se2 | 112.4 (2) |
C2—C3—Cl2 | 126.1 (3) | Cl3—C13—Se2 | 121.5 (2) |
C2—C3—Se1 | 111.7 (2) | N2—C14—C15 | 124.0 (3) |
Cl2—C3—Se1 | 122.1 (2) | N2—C14—Se2 | 114.8 (2) |
N1—C4—C5 | 124.1 (3) | C15—C14—Se2 | 121.2 (2) |
N1—C4—Se1 | 114.5 (2) | C16—C15—C20 | 118.8 (3) |
C5—C4—Se1 | 121.3 (2) | C16—C15—C14 | 121.7 (3) |
C6—C5—C10 | 118.7 (3) | C20—C15—C14 | 119.5 (3) |
C6—C5—C4 | 122.4 (3) | C17—C16—C15 | 120.4 (3) |
C10—C5—C4 | 118.9 (3) | C17—C16—H16A | 119.8 |
C5—C6—C7 | 119.7 (4) | C15—C16—H16A | 119.8 |
C5—C6—H6A | 120.2 | C18—C17—C16 | 120.1 (3) |
C7—C6—H6A | 120.2 | C18—C17—H17A | 120.0 |
C8—C7—C6 | 120.5 (4) | C16—C17—H17A | 120.0 |
C8—C7—H7A | 119.7 | C17—C18—C19 | 120.4 (3) |
C6—C7—H7A | 119.7 | C17—C18—H18A | 119.8 |
C9—C8—C7 | 120.1 (4) | C19—C18—H18A | 119.8 |
C9—C8—H8A | 119.9 | C18—C19—C20 | 120.1 (4) |
C7—C8—H8A | 119.9 | C18—C19—H19A | 120.0 |
C8—C9—C10 | 120.5 (4) | C20—C19—H19A | 120.0 |
C8—C9—H9A | 119.7 | C19—C20—C15 | 120.2 (3) |
C10—C9—H9A | 119.7 | C19—C20—H20A | 119.9 |
C9—C10—C5 | 120.5 (3) | C15—C20—H20A | 119.9 |
C4—N1—C2—C3 | 0.2 (4) | C14—N2—C12—C13 | 0.0 (4) |
C4—N1—C2—C1 | 178.5 (3) | C14—N2—C12—C11 | 178.4 (2) |
Cl1—C1—C2—C3 | −100.3 (4) | Cl4—C11—C12—C13 | −100.8 (3) |
Cl1—C1—C2—N1 | 81.6 (4) | Cl4—C11—C12—N2 | 81.0 (3) |
N1—C2—C3—Cl2 | 179.5 (2) | N2—C12—C13—Cl3 | 179.6 (2) |
C1—C2—C3—Cl2 | 1.3 (5) | C11—C12—C13—Cl3 | 1.4 (5) |
N1—C2—C3—Se1 | 0.4 (4) | N2—C12—C13—Se2 | 0.2 (3) |
C1—C2—C3—Se1 | −177.8 (3) | C11—C12—C13—Se2 | −178.1 (2) |
C4—Se1—C3—C2 | −0.6 (2) | C14—Se2—C13—C12 | −0.2 (2) |
C4—Se1—C3—Cl2 | −179.7 (2) | C14—Se2—C13—Cl3 | −179.7 (2) |
C2—N1—C4—C5 | 179.6 (3) | C12—N2—C14—C15 | 179.6 (2) |
C2—N1—C4—Se1 | −0.6 (3) | C12—N2—C14—Se2 | −0.2 (3) |
C3—Se1—C4—N1 | 0.7 (2) | C13—Se2—C14—N2 | 0.2 (2) |
C3—Se1—C4—C5 | −179.5 (2) | C13—Se2—C14—C15 | −179.6 (2) |
N1—C4—C5—C6 | −172.8 (3) | N2—C14—C15—C16 | −172.1 (3) |
Se1—C4—C5—C6 | 7.4 (4) | Se2—C14—C15—C16 | 7.7 (4) |
N1—C4—C5—C10 | 6.2 (4) | N2—C14—C15—C20 | 6.4 (4) |
Se1—C4—C5—C10 | −173.6 (2) | Se2—C14—C15—C20 | −173.8 (2) |
C10—C5—C6—C7 | −0.8 (5) | C20—C15—C16—C17 | −1.1 (4) |
C4—C5—C6—C7 | 178.2 (3) | C14—C15—C16—C17 | 177.4 (3) |
C5—C6—C7—C8 | 1.7 (6) | C15—C16—C17—C18 | 0.2 (5) |
C6—C7—C8—C9 | −1.2 (7) | C16—C17—C18—C19 | 0.9 (5) |
C7—C8—C9—C10 | −0.1 (6) | C17—C18—C19—C20 | −1.1 (6) |
C8—C9—C10—C5 | 1.1 (5) | C18—C19—C20—C15 | 0.2 (5) |
C6—C5—C10—C9 | −0.6 (4) | C16—C15—C20—C19 | 0.9 (4) |
C4—C5—C10—C9 | −179.6 (3) | C14—C15—C20—C19 | −177.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1B···Cl2 | 0.97 | 2.78 | 3.213 (5) | 108 |
C6—H6A···Se1 | 0.93 | 2.79 | 3.219 (4) | 109 |
C11—H11B···Cl3 | 0.97 | 2.80 | 3.222 (4) | 107 |
C16—H16A···Se2 | 0.93 | 2.76 | 3.200 (3) | 110 |
Experimental details
Crystal data | |
Chemical formula | C10H7Cl2NSe |
Mr | 291.03 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 8.1640 (5), 10.4050 (6), 13.7225 (7) |
α, β, γ (°) | 76.264 (3), 74.357 (3), 86.475 (3) |
V (Å3) | 1090.39 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 3.89 |
Crystal size (mm) | 0.57 × 0.30 × 0.22 |
Data collection | |
Diffractometer | Bruker APEX2 area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.256, 0.423 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17299, 5021, 3550 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.653 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.098, 1.03 |
No. of reflections | 5021 |
No. of parameters | 253 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.42, −0.48 |
Computer programs: APEX2 (Bruker, 2004), SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXTL (Bruker, 2004), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1B···Cl2 | 0.97 | 2.78 | 3.213 (5) | 107.7 |
C6—H6A···Se1 | 0.93 | 2.79 | 3.219 (4) | 109.3 |
C11—H11B···Cl3 | 0.97 | 2.80 | 3.222 (4) | 107.4 |
C16—H16A···Se2 | 0.93 | 2.76 | 3.200 (3) | 110.2 |
Selenium-containing molecules are of considerable biochemical and pharmacological relevance. A prominent example is the antitumor and antiviral active C-glycosyl selenazole selenazofurin (Koketsu & Ishihara, 2003; Geisler et al., 2004). In order to prepare compounds with higher anticancer activity, we planed to synthesize some selenazole derivatives containing amino acids. By reacting 2-phenyl-1,3-selenazole methanol with glycine in sulfuryl dichloride, we unexpectedly obtained the title compound, (I), and obtained single crystals suitable for X-ray diffraction.
The asymmetric unit of (I) contains two independent molecules, quoted 1 and 2 for Se1 and Se2 containing molecules, respectively (Fig. 1). The dihedral angle between phenyl and selenazole rings are 7.25 (9) and 7.47 (9)° for molecules 1 and 2, respectively. The Se—C distances, 1.852 (4), 1.883 (3) Å as well as the bond angle C—Se—C, 83.79 (14) ° in molecule 1, are slightly different than corresponding bond lengths [1.851 (3) and 1.878 (3) Å] and angle [83.25 (13)°] in molecule 2. The N═C and N—C distances in molecule 1 are 1.282 (4) and 1.386 (4) Å; the corresponding distances in molecule 2 are 1.291 (3) and 1.372 (4) Å.
In the asymmetric unit, the dihedral angle between two neighboring phenyl rings is 65.79 (11)°, and angle between two neighboring selenazole rings is 51.12 (9)°. Furthermore, there are weak C—H···Se and C—H···Cl intramolecular hydrogen bonds, involving C6 and Se1, C16 and Se2, C1 and Cl2, C11 and Cl3, forming five-membered rings. Via hydrogen bond interactions, all the skeletal atoms in each independent molecule, except for chloromethyl Cl atoms, are approximately coplanar, with maximum deviations of -0.112 Å for C20 and 0.102 Å for C7.