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The title compound, C14H12BrN2O+·ClO4-, was synthesized from the parent 2-aminooxazole and acetylacetone and characterized by 1H NMR and single-crystal X-ray diffraction. The bromophenyl fragment and the essentially planar nine-membered bicyclic system form a dihedral angle of 10.50 (11)°.
Supporting information
CCDC reference: 627451
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.045
- wR factor = 0.115
- Data-to-parameter ratio = 14.7
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.93
Alert level B
PLAT431_ALERT_2_B Short Inter HL..A Contact Br13 .. O13 .. 2.99 Ang.
PLAT432_ALERT_2_B Short Inter X...Y Contact O13 .. C5 .. 2.84 Ang.
Alert level C
REFLT03_ALERT_3_C Reflection count < 95% complete
From the CIF: _diffrn_reflns_theta_max 75.00
From the CIF: _diffrn_reflns_theta_full 75.00
From the CIF: _reflns_number_total 3090
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 3332
Completeness (_total/calc) 92.74%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.93
PLAT230_ALERT_2_C Hirshfeld Test Diff for C3 - C10 .. 5.97 su
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl1
PLAT432_ALERT_2_C Short Inter X...Y Contact O11 .. C9 .. 2.96 Ang.
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
1 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 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 (Farrugia, 1999).
2-(4-Bromophenyl)-5,7-dimethyl[1,3]oxazolo[3,2-
a]pyrimidin-4-ium
perchlorate
top
Crystal data top
C14H12BrN2O+·ClO4− | F(000) = 808 |
Mr = 403.62 | Dx = 1.660 Mg m−3 |
Monoclinic, P21/c | Melting point: 589 K |
Hall symbol: -P 2ybc | Cu Kα radiation, λ = 1.5418 Å |
a = 15.742 (4) Å | Cell parameters from 25 reflections |
b = 13.292 (4) Å | θ = 30–32° |
c = 7.718 (3) Å | µ = 5.25 mm−1 |
β = 91.14 (2)° | T = 293 K |
V = 1614.6 (9) Å3 | Block, colourless |
Z = 4 | 0.15 × 0.15 × 0.15 mm |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.025 |
Radiation source: Fine-focus sealed tube | θmax = 75.0°, θmin = 2.8° |
Graphite monochromator | h = −19→19 |
ω scans | k = 0→16 |
3354 measured reflections | l = 0→9 |
3090 independent reflections | 1 standard reflections every 60 min |
1986 reflections with I > 2σ(I) | intensity decay: 7% |
Refinement top
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 0.96 | w = 1/[σ2(Fo2) + (0.056P)2] where P = (Fo2 + 2Fc2)/3 |
3090 reflections | (Δ/σ)max = 0.001 |
210 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
Special details top
Experimental. NMR 1H (DMSO-d6/TMS) δ, J (Hz) 9.46 (s, 1H, H-3), 7.97 (m, 3H, (2H,
p-BrPh + H-6)), 7.83 (m, 2H, p-BrPh), 2.91 (s, 3H, 5-CH3),
2.84 (s, 3H, 7-CH3). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.79574 (18) | 0.0765 (2) | −0.1354 (4) | 0.0460 (7) | |
C2 | 0.7566 (2) | 0.1672 (3) | −0.0885 (5) | 0.0488 (9) | |
H2 | 0.7818 | 0.2303 | −0.0794 | 0.059* | |
C3 | 0.6752 (2) | 0.1439 (3) | −0.0598 (5) | 0.0489 (9) | |
O4 | 0.66243 (15) | 0.0418 (2) | −0.0894 (3) | 0.0545 (7) | |
C5 | 0.7370 (2) | 0.0036 (3) | −0.1345 (5) | 0.0498 (9) | |
N6 | 0.7477 (2) | −0.0908 (2) | −0.1702 (5) | 0.0592 (9) | |
C7 | 0.8276 (3) | −0.1156 (3) | −0.2091 (5) | 0.0631 (11) | |
C71 | 0.8421 (3) | −0.2229 (4) | −0.2622 (7) | 0.0866 (16) | |
H71A | 0.8546 | −0.2629 | −0.1613 | 0.130* | |
H71B | 0.8890 | −0.2260 | −0.3395 | 0.130* | |
H71C | 0.7919 | −0.2484 | −0.3198 | 0.130* | |
C8 | 0.8933 (3) | −0.0443 (4) | −0.2074 (5) | 0.0601 (11) | |
H8 | 0.9483 | −0.0649 | −0.2312 | 0.072* | |
C9 | 0.8787 (2) | 0.0534 (3) | −0.1720 (5) | 0.0548 (10) | |
C91 | 0.9411 (2) | 0.1366 (4) | −0.1719 (6) | 0.0668 (12) | |
H91A | 0.9445 | 0.1663 | −0.0586 | 0.100* | |
H91B | 0.9235 | 0.1865 | −0.2549 | 0.100* | |
H91C | 0.9958 | 0.1109 | −0.2020 | 0.100* | |
C10 | 0.6026 (2) | 0.2032 (3) | −0.0045 (5) | 0.0484 (9) | |
C11 | 0.5284 (2) | 0.1561 (4) | 0.0441 (6) | 0.0675 (12) | |
H11 | 0.5251 | 0.0863 | 0.0416 | 0.081* | |
C12 | 0.4589 (2) | 0.2115 (4) | 0.0964 (6) | 0.0661 (12) | |
H12 | 0.4093 | 0.1798 | 0.1304 | 0.079* | |
C13 | 0.4653 (2) | 0.3145 (4) | 0.0967 (6) | 0.0598 (11) | |
Br13 | 0.37035 (3) | 0.39295 (4) | 0.16018 (8) | 0.0827 (2) | |
C14 | 0.5393 (3) | 0.3633 (4) | 0.0515 (6) | 0.0660 (12) | |
H14 | 0.5428 | 0.4330 | 0.0568 | 0.079* | |
C15 | 0.6082 (2) | 0.3071 (3) | −0.0017 (6) | 0.0595 (11) | |
H15 | 0.6578 | 0.3390 | −0.0352 | 0.071* | |
Cl1 | 0.84530 (6) | 0.04819 (8) | 0.33257 (13) | 0.0558 (3) | |
O11 | 0.8082 (3) | 0.0957 (3) | 0.4764 (4) | 0.1070 (14) | |
O12 | 0.8970 (3) | −0.0307 (4) | 0.3935 (5) | 0.1232 (16) | |
O13 | 0.7803 (3) | 0.0099 (4) | 0.2244 (5) | 0.140 (2) | |
O14 | 0.8925 (3) | 0.1175 (3) | 0.2328 (5) | 0.1073 (13) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0582 (15) | 0.0509 (19) | 0.0288 (17) | 0.0037 (13) | −0.0058 (13) | 0.0022 (14) |
C2 | 0.0622 (19) | 0.042 (2) | 0.042 (2) | 0.0032 (16) | −0.0089 (17) | −0.0056 (18) |
C3 | 0.0653 (19) | 0.047 (2) | 0.033 (2) | −0.0006 (17) | −0.0098 (17) | 0.0025 (18) |
O4 | 0.0646 (14) | 0.0476 (16) | 0.0511 (17) | 0.0012 (12) | −0.0053 (12) | −0.0031 (14) |
C5 | 0.0626 (19) | 0.055 (2) | 0.032 (2) | 0.0013 (17) | −0.0074 (16) | 0.0004 (19) |
N6 | 0.082 (2) | 0.045 (2) | 0.051 (2) | 0.0011 (16) | −0.0010 (17) | −0.0045 (17) |
C7 | 0.091 (3) | 0.061 (3) | 0.037 (3) | 0.016 (2) | 0.000 (2) | 0.002 (2) |
C71 | 0.111 (4) | 0.063 (3) | 0.087 (4) | 0.016 (3) | 0.014 (3) | −0.017 (3) |
C8 | 0.078 (2) | 0.067 (3) | 0.036 (2) | 0.021 (2) | 0.0028 (19) | 0.009 (2) |
C9 | 0.070 (2) | 0.066 (3) | 0.028 (2) | 0.0098 (19) | −0.0011 (17) | 0.012 (2) |
C91 | 0.061 (2) | 0.073 (3) | 0.067 (3) | 0.004 (2) | 0.003 (2) | 0.008 (3) |
C10 | 0.0524 (17) | 0.052 (2) | 0.041 (2) | 0.0090 (16) | −0.0065 (16) | 0.0010 (19) |
C11 | 0.068 (2) | 0.056 (3) | 0.079 (3) | −0.0069 (19) | 0.005 (2) | −0.012 (2) |
C12 | 0.062 (2) | 0.063 (3) | 0.073 (3) | −0.0029 (19) | 0.005 (2) | −0.007 (3) |
C13 | 0.0589 (19) | 0.068 (3) | 0.052 (3) | 0.0128 (19) | −0.0040 (18) | 0.000 (2) |
Br13 | 0.0708 (3) | 0.0805 (4) | 0.0972 (5) | 0.0196 (2) | 0.0086 (3) | −0.0018 (3) |
C14 | 0.073 (2) | 0.054 (3) | 0.071 (3) | 0.0089 (19) | 0.003 (2) | 0.010 (2) |
C15 | 0.0564 (18) | 0.053 (3) | 0.069 (3) | 0.0008 (17) | −0.0058 (19) | 0.009 (2) |
Cl1 | 0.0673 (5) | 0.0613 (6) | 0.0386 (6) | 0.0022 (4) | −0.0063 (4) | 0.0021 (5) |
O11 | 0.155 (3) | 0.115 (3) | 0.051 (2) | 0.062 (3) | 0.010 (2) | 0.001 (2) |
O12 | 0.168 (4) | 0.127 (4) | 0.075 (3) | 0.073 (3) | 0.009 (3) | 0.011 (3) |
O13 | 0.153 (3) | 0.198 (5) | 0.068 (3) | −0.104 (4) | −0.036 (2) | 0.048 (3) |
O14 | 0.120 (3) | 0.119 (3) | 0.082 (3) | −0.045 (2) | 0.000 (2) | 0.011 (2) |
Geometric parameters (Å, º) top
N1—C5 | 1.339 (5) | C91—H91A | 0.96 |
N1—C9 | 1.376 (4) | C91—H91B | 0.96 |
N1—C2 | 1.406 (4) | C91—H91C | 0.96 |
C2—C3 | 1.341 (5) | C10—C11 | 1.383 (5) |
C2—H2 | 0.93 | C10—C15 | 1.385 (5) |
C3—O4 | 1.390 (5) | C11—C12 | 1.385 (6) |
C3—C10 | 1.458 (5) | C11—H11 | 0.93 |
O4—C5 | 1.331 (4) | C12—C13 | 1.373 (6) |
C5—N6 | 1.296 (5) | C12—H12 | 0.93 |
N6—C7 | 1.341 (5) | C13—C14 | 1.384 (6) |
C7—C8 | 1.403 (6) | C13—Br13 | 1.895 (4) |
C7—C71 | 1.502 (6) | C14—C15 | 1.385 (5) |
C71—H71A | 0.96 | C14—H14 | 0.93 |
C71—H71B | 0.96 | C15—H15 | 0.93 |
C71—H71C | 0.96 | Cl1—O13 | 1.403 (4) |
C8—C9 | 1.348 (6) | Cl1—O12 | 1.403 (4) |
C8—H8 | 0.93 | Cl1—O11 | 1.414 (3) |
C9—C91 | 1.478 (6) | Cl1—O14 | 1.420 (4) |
| | | |
C5—N1—C9 | 119.9 (3) | C9—C91—H91B | 109.5 |
C5—N1—C2 | 108.2 (3) | H91A—C91—H91B | 109.5 |
C9—N1—C2 | 131.8 (3) | C9—C91—H91C | 109.5 |
C3—C2—N1 | 105.6 (3) | H91A—C91—H91C | 109.5 |
C3—C2—H2 | 127.2 | H91B—C91—H91C | 109.5 |
N1—C2—H2 | 127.2 | C11—C10—C15 | 120.0 (4) |
C2—C3—O4 | 109.5 (3) | C11—C10—C3 | 120.4 (4) |
C2—C3—C10 | 132.9 (4) | C15—C10—C3 | 119.6 (3) |
O4—C3—C10 | 117.6 (3) | C10—C11—C12 | 121.0 (4) |
C5—O4—C3 | 106.8 (3) | C10—C11—H11 | 119.5 |
N6—C5—O4 | 122.9 (3) | C12—C11—H11 | 119.5 |
N6—C5—N1 | 127.3 (4) | C13—C12—C11 | 118.2 (4) |
O4—C5—N1 | 109.8 (3) | C13—C12—H12 | 120.9 |
C5—N6—C7 | 114.4 (4) | C11—C12—H12 | 120.9 |
N6—C7—C8 | 121.8 (4) | C12—C13—C14 | 121.9 (4) |
N6—C7—C71 | 116.3 (4) | C12—C13—Br13 | 119.4 (3) |
C8—C7—C71 | 121.9 (4) | C14—C13—Br13 | 118.7 (3) |
C7—C71—H71A | 109.5 | C13—C14—C15 | 119.4 (4) |
C7—C71—H71B | 109.5 | C13—C14—H14 | 120.3 |
H71A—C71—H71B | 109.5 | C15—C14—H14 | 120.3 |
C7—C71—H71C | 109.5 | C10—C15—C14 | 119.5 (4) |
H71A—C71—H71C | 109.5 | C10—C15—H15 | 120.2 |
H71B—C71—H71C | 109.5 | C14—C15—H15 | 120.2 |
C9—C8—C7 | 121.6 (4) | O13—Cl1—O12 | 109.9 (3) |
C9—C8—H8 | 119.2 | O13—Cl1—O11 | 108.7 (3) |
C7—C8—H8 | 119.2 | O12—Cl1—O11 | 108.5 (2) |
C8—C9—N1 | 115.0 (4) | O13—Cl1—O14 | 107.2 (2) |
C8—C9—C91 | 127.2 (4) | O12—Cl1—O14 | 111.1 (3) |
N1—C9—C91 | 117.8 (4) | O11—Cl1—O14 | 111.4 (3) |
C9—C91—H91A | 109.5 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O11i | 0.93 | 2.39 | 3.290 (6) | 164 |
C11—H11···O4 | 0.93 | 2.48 | 2.812 (5) | 101 |
C15—H15···O11i | 0.93 | 2.52 | 3.411 (6) | 160 |
C91—H91A···O14 | 0.96 | 2.49 | 3.241 (6) | 135 |
C91—H91C···O12ii | 0.96 | 2.50 | 3.402 (6) | 156 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+2, −y, −z. |
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