Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806037299/lh2161sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806037299/lh21612sup2.hkl |
CCDC reference: 624900
Data collection: CAD-4 EXPRESS; cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wokadlo, (1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).
C12H8BrN2O+·ClO4− | F(000) = 744 |
Mr = 375.56 | Dx = 1.879 Mg m−3 |
Monoclinic, P21/n | Melting point: 553 K |
Hall symbol: -P 2yn | Cu Kα radiation, λ = 1.5418 Å |
a = 6.291 (2) Å | Cell parameters from 25 reflections |
b = 12.052 (2) Å | θ = 34–36° |
c = 17.688 (4) Å | µ = 6.33 mm−1 |
β = 98.19 (2)° | T = 293 K |
V = 1327.4 (6) Å3 | Prism, colourless |
Z = 4 | 0.15 × 0.15 × 0.15 mm |
Enraf–Nonius CAD 4 diffractometer | Rint = 0.084 |
Radiation source: Fine-focus sealed tube | θmax = 74.9°, θmin = 4.5° |
Graphite monochromator | h = −7→7 |
ω scans | k = 0→15 |
2811 measured reflections | l = 0→22 |
2714 independent reflections | 1 standard reflections every 60 min |
2375 reflections with I > 2σ(I) | intensity decay: 3% |
Refinement on F2 | Primary atom site location: Direct |
Least-squares matrix: Full | Secondary atom site location: Difmap |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: Geom |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 0.92 | w = 1/[σ2(Fo2) + (0.0909P)2 + 0.38P] where P = (Fo2 + 2Fc2)/3 |
2714 reflections | (Δ/σ)max = 0.001 |
190 parameters | Δρmax = 0.48 e Å−3 |
0 restraints | Δρmin = −0.47 e Å−3 |
Experimental. 1-[2-(4-Bromophenyl)-2-oxoethyl] pyrimidin-2(1H)-one (1) was prepared analogously to previously described procedure (Rybakov et al., 2006). Hydrochloride of pyrimidone-2 (1) (26.5 g, 0.2 mol) was suspended in 500 ml of dry acetone. Solution of 0.1 mol of p-bromophenacylbromide in 100 ml acetone and 0.4 mol K2CO3 was added with stirring. Reaction mixture was stirred for 2 days at room temperature, and then the solvent was evaporated in vacuum. The residue was washed with water and then with ethylacetate. The white solid product was isolated by suction and recrystallized from acetonitrile. Yield 95%, m.p. 510–512 K. IR (Nujol): 1700, 1660 cm-1. 1H NMR (360 MHz, DMSO-d6): δ J(Hz) 5.43 (s, 2H, CH2), 6.41 (m, 1H, H-5), 7.72 (m, 2H, H—Ar, BB'), 7.99 (m, 2H, H—Ar, AA'), 8.08 (m, 1H, H-4), 8.57 (m, 1H, H-6). Calculated, %: C 49.17 H 3.09 N 9.56. C12H9BrN2O2. Found, %: C 48.75 H 2.89 N 9.36. 2-(p-bromophenyl)oxazolo[3,2-a]pyrimidinium perchlorate (2). 1H NMR (360 MHz, DMSO-d6): δ J(Hz) 7.81 (m, 2H, H—Ar, BB'), 8.02 (m, 2H, H—Ar, AA'), 8.14 (dd, J67 = 4.6 Hz, J65 = 6.3 Hz, 1H, H-6), 9.31 (s, 1H, H-3), 9.36 (dd, J76 = 4.6 Hz, J75 = 1.8 Hz, 1H, H-7), 9.68 (dd, J56 = 6.3 Hz, J57 = 1.8 Hz, 1H, H-5). Calculated, %: C 38.38 H 2.15 N 7.46. C12H8BrClN2O5. Found, %: C 38.24 H 1.86 N 7.71. |
x | y | z | Uiso*/Ueq | ||
Br13 | 0.04764 (4) | 0.07749 (3) | −0.111497 (17) | 0.04885 (15) | |
N1 | 1.1667 (3) | 0.32306 (15) | 0.13154 (10) | 0.0294 (4) | |
C2 | 0.9824 (4) | 0.25917 (19) | 0.12708 (13) | 0.0337 (5) | |
H2 | 0.9388 | 0.2163 | 0.1658 | 0.040* | |
C3 | 0.8792 (4) | 0.27135 (17) | 0.05578 (12) | 0.0282 (4) | |
O4 | 0.9946 (3) | 0.34262 (14) | 0.01574 (8) | 0.0322 (3) | |
C5 | 1.1668 (4) | 0.37276 (18) | 0.06303 (12) | 0.0286 (4) | |
N6 | 1.3173 (4) | 0.43928 (18) | 0.04443 (12) | 0.0372 (5) | |
C7 | 1.4759 (4) | 0.4589 (2) | 0.10101 (15) | 0.0394 (6) | |
H7 | 1.5863 | 0.5057 | 0.0913 | 0.047* | |
C8 | 1.4867 (4) | 0.4136 (2) | 0.17387 (15) | 0.0382 (6) | |
H8 | 1.6016 | 0.4300 | 0.2113 | 0.046* | |
C9 | 1.3271 (4) | 0.34487 (19) | 0.18955 (13) | 0.0338 (5) | |
H9 | 1.3278 | 0.3142 | 0.2378 | 0.041* | |
C10 | 0.6796 (4) | 0.22816 (18) | 0.01586 (12) | 0.0306 (5) | |
C11 | 0.6130 (4) | 0.2531 (2) | −0.06063 (13) | 0.0345 (5) | |
H11 | 0.6964 | 0.2993 | −0.0866 | 0.041* | |
C12 | 0.4233 (4) | 0.2094 (2) | −0.09832 (13) | 0.0364 (5) | |
H12 | 0.3775 | 0.2268 | −0.1493 | 0.044* | |
C13 | 0.3052 (4) | 0.1409 (2) | −0.05974 (13) | 0.0344 (5) | |
C14 | 0.3618 (4) | 0.1158 (2) | 0.01629 (13) | 0.0349 (5) | |
H14 | 0.2741 | 0.0714 | 0.0418 | 0.042* | |
C15 | 0.5530 (4) | 0.1584 (2) | 0.05422 (12) | 0.0323 (5) | |
H15 | 0.5969 | 0.1405 | 0.1052 | 0.039* | |
Cl1 | 0.01661 (10) | 0.57078 (5) | 0.23198 (3) | 0.03760 (17) | |
O11 | −0.1441 (5) | 0.6452 (3) | 0.25201 (16) | 0.0786 (8) | |
O12 | 0.0014 (5) | 0.4655 (3) | 0.26678 (18) | 0.0850 (9) | |
O13 | −0.0160 (5) | 0.5490 (3) | 0.15224 (18) | 0.0840 (8) | |
O14 | 0.2249 (5) | 0.6165 (3) | 0.24949 (19) | 0.0863 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br13 | 0.0423 (2) | 0.0571 (2) | 0.0461 (2) | −0.00886 (12) | 0.00254 (13) | −0.00393 (12) |
N1 | 0.0384 (10) | 0.0227 (9) | 0.0285 (8) | 0.0020 (7) | 0.0101 (7) | 0.0025 (7) |
C2 | 0.0408 (12) | 0.0252 (11) | 0.0362 (11) | −0.0007 (9) | 0.0098 (9) | 0.0048 (9) |
C3 | 0.0344 (11) | 0.0197 (9) | 0.0328 (10) | 0.0035 (8) | 0.0130 (8) | −0.0012 (8) |
O4 | 0.0388 (8) | 0.0317 (8) | 0.0269 (7) | 0.0010 (7) | 0.0077 (6) | 0.0040 (6) |
C5 | 0.0360 (11) | 0.0249 (10) | 0.0264 (9) | 0.0076 (9) | 0.0092 (8) | 0.0013 (8) |
N6 | 0.0403 (11) | 0.0355 (11) | 0.0387 (10) | −0.0017 (9) | 0.0151 (9) | 0.0089 (8) |
C7 | 0.0454 (14) | 0.0286 (12) | 0.0486 (14) | −0.0067 (10) | 0.0220 (11) | −0.0067 (10) |
C8 | 0.0395 (13) | 0.0337 (12) | 0.0404 (13) | 0.0007 (10) | 0.0023 (10) | −0.0050 (9) |
C9 | 0.0436 (12) | 0.0272 (11) | 0.0297 (10) | −0.0016 (10) | 0.0018 (9) | −0.0031 (8) |
C10 | 0.0388 (11) | 0.0224 (10) | 0.0313 (10) | 0.0059 (9) | 0.0075 (8) | −0.0076 (8) |
C11 | 0.0422 (12) | 0.0334 (11) | 0.0304 (10) | 0.0021 (10) | 0.0144 (9) | 0.0013 (9) |
C12 | 0.0396 (12) | 0.0407 (13) | 0.0281 (10) | 0.0044 (10) | 0.0018 (9) | 0.0027 (9) |
C13 | 0.0367 (12) | 0.0359 (12) | 0.0311 (10) | 0.0065 (10) | 0.0065 (9) | −0.0091 (9) |
C14 | 0.0376 (12) | 0.0346 (12) | 0.0351 (11) | −0.0014 (10) | 0.0140 (9) | −0.0021 (9) |
C15 | 0.0375 (12) | 0.0313 (11) | 0.0291 (10) | −0.0024 (9) | 0.0077 (8) | 0.0021 (8) |
Cl1 | 0.0424 (3) | 0.0317 (3) | 0.0392 (3) | 0.0033 (2) | 0.0077 (2) | −0.0078 (2) |
O11 | 0.0806 (18) | 0.0799 (19) | 0.0769 (16) | 0.0289 (15) | 0.0169 (14) | −0.0084 (14) |
O12 | 0.097 (2) | 0.0731 (18) | 0.0895 (19) | 0.0289 (16) | 0.0290 (16) | 0.0060 (15) |
O13 | 0.090 (2) | 0.086 (2) | 0.0774 (18) | 0.0256 (17) | 0.0172 (15) | −0.0076 (16) |
O14 | 0.083 (2) | 0.0756 (19) | 0.101 (2) | 0.0190 (16) | 0.0133 (17) | −0.0188 (16) |
Br13—C13 | 1.904 (3) | C9—H9 | 0.9300 |
N1—C5 | 1.352 (3) | C10—C11 | 1.391 (3) |
N1—C9 | 1.359 (3) | C10—C15 | 1.398 (3) |
N1—C2 | 1.384 (3) | C11—C12 | 1.385 (4) |
C2—C3 | 1.342 (3) | C11—H11 | 0.9300 |
C2—H2 | 0.9300 | C12—C13 | 1.358 (4) |
C3—O4 | 1.383 (3) | C12—H12 | 0.9300 |
C3—C10 | 1.447 (3) | C13—C14 | 1.375 (3) |
O4—C5 | 1.322 (3) | C14—C15 | 1.390 (3) |
C5—N6 | 1.317 (3) | C14—H14 | 0.9300 |
N6—C7 | 1.330 (3) | C15—H15 | 0.9300 |
C7—C8 | 1.392 (4) | Cl1—O14 | 1.415 (4) |
C7—H7 | 0.9300 | Cl1—O12 | 1.419 (3) |
C8—C9 | 1.360 (4) | Cl1—O13 | 1.420 (3) |
C8—H8 | 0.9300 | Cl1—O11 | 1.433 (3) |
C5—N1—C9 | 119.7 (2) | C11—C10—C3 | 121.1 (2) |
C5—N1—C2 | 107.63 (19) | C15—C10—C3 | 119.6 (2) |
C9—N1—C2 | 132.6 (2) | C12—C11—C10 | 120.4 (2) |
C3—C2—N1 | 106.4 (2) | C12—C11—H11 | 119.8 |
C3—C2—H2 | 126.8 | C10—C11—H11 | 119.8 |
N1—C2—H2 | 126.8 | C13—C12—C11 | 119.0 (2) |
C2—C3—O4 | 109.3 (2) | C13—C12—H12 | 120.5 |
C2—C3—C10 | 133.6 (2) | C11—C12—H12 | 120.5 |
O4—C3—C10 | 117.12 (19) | C12—C13—C14 | 122.8 (2) |
C5—O4—C3 | 106.82 (17) | C12—C13—Br13 | 119.43 (18) |
N6—C5—O4 | 124.2 (2) | C14—C13—Br13 | 117.80 (19) |
N6—C5—N1 | 125.9 (2) | C13—C14—C15 | 118.5 (2) |
O4—C5—N1 | 109.9 (2) | C13—C14—H14 | 120.8 |
C5—N6—C7 | 114.1 (2) | C15—C14—H14 | 120.8 |
N6—C7—C8 | 124.0 (2) | C14—C15—C10 | 120.1 (2) |
N6—C7—H7 | 118.0 | C14—C15—H15 | 120.0 |
C8—C7—H7 | 118.0 | C10—C15—H15 | 120.0 |
C9—C8—C7 | 119.2 (2) | O14—Cl1—O12 | 111.7 (2) |
C9—C8—H8 | 120.4 | O14—Cl1—O13 | 106.7 (2) |
C7—C8—H8 | 120.4 | O12—Cl1—O13 | 104.86 (19) |
N1—C9—C8 | 117.0 (2) | O14—Cl1—O11 | 111.53 (17) |
N1—C9—H9 | 121.5 | O12—Cl1—O11 | 111.00 (18) |
C8—C9—H9 | 121.5 | O13—Cl1—O11 | 110.72 (17) |
C11—C10—C15 | 119.2 (2) |