organic compounds
In the title molecular structure, C20H8Cl4N4O, the 1,3,4-triazole ring is twisted with an r.m.s. deviation of 0.0035 Å. One of the quinolinyl substituents makes a dihedral angle of 55.8 (1)° with respect to the central ring, while the other is rotated by 71.7 (1)°; these twists are necessary to relieve steric crowding.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806019702/lh2088sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806019702/lh2088Isup2.hkl |
CCDC reference: 613768
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.003 Å
- R factor = 0.038
- wR factor = 0.103
- Data-to-parameter ratio = 16.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT431_ALERT_2_C Short Inter HL..A Contact Cl2 .. N4 .. 3.09 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Cl3 .. O1 .. 3.12 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and SHELXTL (Bruker, 2004); software used to prepare material for publication: SHELXL97.
2,5-Bis(3,7-dichloroquinolin-8-yl)-1,3,4-oxadiazole top
Crystal data top
C20H8Cl4N4O | F(000) = 1856 |
Mr = 462.10 | Dx = 1.631 Mg m−3 |
Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2n 2ab | Cell parameters from 3645 reflections |
a = 14.1016 (8) Å | θ = 2.5–24.5° |
b = 9.8811 (6) Å | µ = 0.65 mm−1 |
c = 27.016 (2) Å | T = 295 K |
V = 3764.4 (4) Å3 | Block, colorless |
Z = 8 | 0.27 × 0.17 × 0.16 mm |
Data collection top
Bruker APEX-II area-detector diffractometer | 2953 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.037 |
Graphite monochromator | θmax = 27.5°, θmin = 2.5° |
φ and ω scans | h = −18→17 |
21631 measured reflections | k = −12→12 |
4317 independent reflections | l = −32→35 |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.103 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0437P)2 + 1.1566P] where P = (Fo2 + 2Fc2)/3 |
4317 reflections | (Δ/σ)max = 0.001 |
262 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.30770 (5) | 0.63219 (6) | 0.41230 (2) | 0.0586 (2) | |
Cl2 | 0.39529 (4) | 0.00516 (6) | 0.61656 (2) | 0.0534 (2) | |
Cl3 | 0.12054 (5) | −0.14164 (6) | 0.69643 (3) | 0.0670 (2) | |
Cl4 | 0.12485 (6) | 0.61943 (8) | 0.83252 (3) | 0.0794 (2) | |
O1 | 0.2300 (1) | 0.1808 (2) | 0.6414 (1) | 0.0389 (3) | |
N1 | 0.2294 (1) | 0.3725 (2) | 0.5155 (1) | 0.0396 (4) | |
N2 | 0.1411 (1) | 0.1389 (2) | 0.5766 (1) | 0.0473 (5) | |
N3 | 0.0863 (1) | 0.1186 (2) | 0.6201 (1) | 0.0502 (5) | |
N4 | 0.1303 (1) | 0.3689 (2) | 0.7188 (1) | 0.0464 (5) | |
C1 | 0.3958 (2) | 0.4295 (2) | 0.4617 (1) | 0.0429 (5) | |
C2 | 0.3143 (2) | 0.4993 (2) | 0.4542 (1) | 0.0412 (5) | |
C3 | 0.2323 (2) | 0.4667 (2) | 0.4814 (1) | 0.0424 (5) | |
C4 | 0.3111 (1) | 0.3023 (2) | 0.5246 (1) | 0.0352 (4) | |
C5 | 0.3959 (2) | 0.3266 (2) | 0.4978 (1) | 0.0387 (5) | |
C6 | 0.4777 (2) | 0.2497 (2) | 0.5088 (1) | 0.0484 (6) | |
C7 | 0.4757 (2) | 0.1548 (2) | 0.5450 (1) | 0.0490 (6) | |
C8 | 0.3923 (2) | 0.1311 (2) | 0.5720 (1) | 0.0404 (5) | |
C9 | 0.3103 (1) | 0.2024 (2) | 0.5627 (1) | 0.0355 (4) | |
C10 | 0.2236 (2) | 0.1752 (2) | 0.5913 (1) | 0.0360 (5) | |
C11 | 0.1423 (2) | 0.1432 (2) | 0.6564 (1) | 0.0384 (5) | |
C12 | 0.1279 (1) | 0.1289 (2) | 0.7103 (1) | 0.0370 (5) | |
C13 | 0.1212 (2) | 0.0033 (2) | 0.7319 (1) | 0.0428 (5) | |
C14 | 0.1161 (2) | −0.0118 (2) | 0.7837 (1) | 0.0492 (6) | |
C15 | 0.1155 (2) | 0.0992 (2) | 0.8132 (1) | 0.0473 (6) | |
C16 | 0.1201 (1) | 0.2301 (2) | 0.7930 (1) | 0.0387 (5) | |
C17 | 0.1267 (1) | 0.2452 (2) | 0.7409 (1) | 0.0370 (5) | |
C18 | 0.1299 (2) | 0.4764 (2) | 0.7470 (1) | 0.0530 (6) | |
C19 | 0.1243 (2) | 0.4701 (2) | 0.7990 (1) | 0.0500 (6) | |
C20 | 0.1183 (2) | 0.3486 (2) | 0.8219 (1) | 0.0471 (6) | |
H1 | 0.4501 | 0.4490 | 0.4435 | 0.051* | |
H3 | 0.1771 | 0.5148 | 0.4749 | 0.051* | |
H6 | 0.5333 | 0.2642 | 0.4910 | 0.058* | |
H7 | 0.5300 | 0.1050 | 0.5520 | 0.059* | |
H14 | 0.1133 | −0.0977 | 0.7976 | 0.059* | |
H15 | 0.1118 | 0.0885 | 0.8473 | 0.057* | |
H18 | 0.1336 | 0.5610 | 0.7321 | 0.064* | |
H20 | 0.1130 | 0.3435 | 0.8562 | 0.057* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0820 (5) | 0.0501 (4) | 0.0438 (3) | −0.0001 (3) | 0.0032 (3) | 0.0125 (3) |
Cl2 | 0.0563 (4) | 0.0556 (4) | 0.0485 (3) | 0.0018 (3) | −0.0039 (3) | 0.0157 (3) |
Cl3 | 0.0931 (5) | 0.0459 (4) | 0.0620 (4) | 0.0077 (3) | 0.0145 (3) | −0.0054 (3) |
Cl4 | 0.0986 (6) | 0.0588 (4) | 0.0808 (5) | −0.0112 (4) | 0.0153 (4) | −0.0234 (4) |
O1 | 0.040 (1) | 0.051 (1) | 0.026 (1) | −0.009 (1) | 0.002 (1) | −0.001 (1) |
N1 | 0.042 (1) | 0.042 (1) | 0.034 (1) | 0.001 (1) | 0.003 (1) | −0.001 (1) |
N2 | 0.042 (1) | 0.068 (1) | 0.032 (1) | −0.009 (1) | 0.002 (1) | 0.003 (1) |
N3 | 0.040 (1) | 0.076 (1) | 0.035 (1) | −0.011 (1) | 0.002 (1) | 0.005 (1) |
N4 | 0.055 (1) | 0.044 (1) | 0.040 (1) | −0.001 (1) | 0.002 (1) | 0.008 (1) |
C1 | 0.049 (1) | 0.046 (1) | 0.034 (1) | −0.007 (1) | 0.010 (1) | −0.001 (1) |
C2 | 0.058 (1) | 0.038 (1) | 0.028 (1) | −0.002 (1) | 0.001 (1) | 0.000 (1) |
C3 | 0.048 (1) | 0.044 (1) | 0.035 (1) | 0.002 (1) | −0.002 (1) | −0.002 (1) |
C4 | 0.039 (1) | 0.039 (1) | 0.027 (1) | −0.003 (1) | 0.002 (1) | −0.003 (1) |
C5 | 0.042 (1) | 0.043 (1) | 0.031 (1) | −0.003 (1) | 0.004 (1) | −0.001 (1) |
C6 | 0.040 (1) | 0.059 (1) | 0.047 (1) | 0.000 (1) | 0.011 (1) | 0.006 (1) |
C7 | 0.039 (1) | 0.059 (2) | 0.049 (1) | 0.005 (1) | 0.002 (1) | 0.007 (1) |
C8 | 0.045 (1) | 0.043 (1) | 0.033 (1) | −0.004 (1) | −0.001 (1) | 0.003 (1) |
C9 | 0.039 (1) | 0.040 (1) | 0.028 (1) | −0.002 (1) | 0.000 (1) | −0.003 (1) |
C10 | 0.042 (1) | 0.041 (1) | 0.025 (1) | −0.002 (1) | −0.001 (1) | 0.000 (1) |
C11 | 0.038 (1) | 0.044 (1) | 0.034 (1) | −0.004 (1) | 0.003 (1) | 0.002 (1) |
C12 | 0.033 (1) | 0.048 (1) | 0.030 (1) | 0.001 (1) | 0.003 (1) | 0.005 (1) |
C13 | 0.042 (1) | 0.042 (1) | 0.044 (1) | 0.004 (1) | 0.008 (1) | 0.003 (1) |
C14 | 0.054 (1) | 0.048 (1) | 0.046 (1) | 0.006 (1) | 0.009 (1) | 0.017 (1) |
C15 | 0.050 (1) | 0.059 (2) | 0.033 (1) | 0.004 (1) | 0.005 (1) | 0.011 (1) |
C16 | 0.033 (1) | 0.051 (1) | 0.032 (1) | 0.000 (1) | 0.002 (1) | 0.005 (1) |
C17 | 0.033 (1) | 0.044 (1) | 0.034 (1) | 0.000 (1) | 0.002 (1) | 0.006 (1) |
C18 | 0.062 (2) | 0.041 (1) | 0.056 (1) | −0.003 (1) | 0.006 (1) | 0.007 (1) |
C19 | 0.050 (1) | 0.048 (1) | 0.053 (1) | −0.003 (1) | 0.004 (1) | −0.003 (1) |
C20 | 0.044 (1) | 0.061 (2) | 0.036 (1) | 0.000 (1) | 0.002 (1) | −0.003 (1) |
Geometric parameters (Å, º) top
Cl1—C2 | 1.736 (2) | C8—C9 | 1.378 (3) |
Cl2—C8 | 1.732 (2) | C9—C10 | 1.470 (3) |
Cl3—C13 | 1.724 (2) | C11—C12 | 1.477 (3) |
Cl4—C19 | 1.732 (2) | C12—C13 | 1.375 (3) |
O1—C11 | 1.354 (2) | C12—C17 | 1.416 (3) |
O1—C10 | 1.358 (2) | C13—C14 | 1.409 (3) |
N1—C3 | 1.309 (3) | C14—C15 | 1.355 (3) |
N1—C4 | 1.368 (3) | C15—C16 | 1.404 (3) |
N2—C10 | 1.280 (3) | C16—C20 | 1.408 (3) |
N2—N3 | 1.420 (2) | C16—C17 | 1.419 (3) |
N3—C11 | 1.282 (3) | C18—C19 | 1.408 (3) |
N4—C18 | 1.307 (3) | C19—C20 | 1.353 (3) |
N4—C17 | 1.361 (3) | C1—H1 | 0.93 |
C1—C2 | 1.355 (3) | C3—H3 | 0.93 |
C1—C5 | 1.409 (3) | C6—H6 | 0.93 |
C2—C3 | 1.408 (3) | C7—H7 | 0.93 |
C4—C5 | 1.418 (3) | C14—H14 | 0.93 |
C4—C9 | 1.427 (3) | C15—H15 | 0.93 |
C5—C6 | 1.413 (3) | C18—H18 | 0.93 |
C6—C7 | 1.355 (3) | C20—H20 | 0.93 |
C7—C8 | 1.403 (3) | ||
C11—O1—C10 | 103.0 (2) | C12—C13—C14 | 121.4 (2) |
C3—N1—C4 | 117.4 (2) | C12—C13—Cl3 | 120.9 (2) |
C10—N2—N3 | 106.1 (2) | C14—C13—Cl3 | 117.7 (2) |
C11—N3—N2 | 105.7 (2) | C15—C14—C13 | 119.9 (2) |
C18—N4—C17 | 118.3 (2) | C14—C15—C16 | 121.1 (2) |
C2—C1—C5 | 118.2 (2) | C15—C16—C20 | 123.4 (2) |
C1—C2—C3 | 120.1 (2) | C15—C16—C17 | 119.0 (2) |
C1—C2—Cl1 | 121.9 (2) | C20—C16—C17 | 117.6 (2) |
C3—C2—Cl1 | 118.0 (2) | N4—C17—C12 | 118.2 (2) |
N1—C3—C2 | 123.8 (2) | N4—C17—C16 | 122.1 (2) |
N1—C4—C5 | 122.2 (2) | C12—C17—C16 | 119.6 (2) |
N1—C4—C9 | 118.3 (2) | N4—C18—C19 | 123.0 (2) |
C5—C4—C9 | 119.5 (2) | C20—C19—C18 | 120.0 (2) |
C1—C5—C4 | 118.3 (2) | C20—C19—Cl4 | 121.1 (2) |
C1—C5—C6 | 122.3 (2) | C18—C19—Cl4 | 118.9 (2) |
C4—C5—C6 | 119.4 (2) | C19—C20—C16 | 118.9 (2) |
C7—C6—C5 | 120.4 (2) | C2—C1—H1 | 120.9 |
C6—C7—C8 | 120.6 (2) | C5—C1—H1 | 120.9 |
C9—C8—C7 | 121.6 (2) | N1—C3—H3 | 118.1 |
C9—C8—Cl2 | 120.9 (2) | C2—C3—H3 | 118.1 |
C7—C8—Cl2 | 117.5 (2) | C7—C6—H6 | 119.8 |
C8—C9—C4 | 118.5 (2) | C5—C6—H6 | 119.8 |
C8—C9—C10 | 120.7 (2) | C6—C7—H7 | 119.7 |
C4—C9—C10 | 120.8 (2) | C8—C7—H7 | 119.7 |
N2—C10—O1 | 112.4 (2) | C15—C14—H14 | 120.1 |
N2—C10—C9 | 130.1 (2) | C13—C14—H14 | 120.1 |
O1—C10—C9 | 117.4 (2) | C14—C15—H15 | 119.4 |
N3—C11—O1 | 112.7 (2) | C16—C15—H15 | 119.4 |
N3—C11—C12 | 130.7 (2) | N4—C18—H18 | 118.5 |
O1—C11—C12 | 116.5 (2) | C19—C18—H18 | 118.5 |
C13—C12—C17 | 118.9 (2) | C19—C20—H20 | 120.6 |
C13—C12—C11 | 121.0 (2) | C16—C20—H20 | 120.6 |
C17—C12—C11 | 120.0 (2) | ||
C10—N2—N3—C11 | −0.8 (3) | N2—N3—C11—O1 | 1.0 (3) |
C5—C1—C2—C3 | −1.2 (3) | N2—N3—C11—C12 | −174.7 (2) |
C5—C1—C2—Cl1 | 177.5 (2) | C10—O1—C11—N3 | −0.8 (2) |
C4—N1—C3—C2 | −0.1 (3) | C10—O1—C11—C12 | 175.5 (2) |
C1—C2—C3—N1 | 1.6 (3) | N3—C11—C12—C13 | 69.9 (3) |
Cl1—C2—C3—N1 | −177.2 (2) | O1—C11—C12—C13 | −105.7 (2) |
C3—N1—C4—C5 | −1.7 (3) | N3—C11—C12—C17 | −114.1 (3) |
C3—N1—C4—C9 | 177.9 (2) | O1—C11—C12—C17 | 70.4 (3) |
C2—C1—C5—C4 | −0.5 (3) | C17—C12—C13—C14 | −1.9 (3) |
C2—C1—C5—C6 | −179.1 (2) | C11—C12—C13—C14 | 174.2 (2) |
N1—C4—C5—C1 | 2.0 (3) | C17—C12—C13—Cl3 | 179.1 (2) |
C9—C4—C5—C1 | −177.6 (2) | C11—C12—C13—Cl3 | −4.9 (3) |
N1—C4—C5—C6 | −179.3 (2) | C12—C13—C14—C15 | 1.6 (3) |
C9—C4—C5—C6 | 1.1 (3) | Cl3—C13—C14—C15 | −179.3 (2) |
C1—C5—C6—C7 | 177.7 (2) | C13—C14—C15—C16 | −0.3 (3) |
C4—C5—C6—C7 | −0.9 (3) | C14—C15—C16—C20 | 179.1 (2) |
C5—C6—C7—C8 | 0.3 (4) | C14—C15—C16—C17 | −0.7 (3) |
C6—C7—C8—C9 | 0.2 (3) | C18—N4—C17—C12 | −179.5 (2) |
C6—C7—C8—Cl2 | 178.5 (2) | C18—N4—C17—C16 | 1.8 (3) |
C7—C8—C9—C4 | 0.0 (3) | C13—C12—C17—N4 | −177.9 (2) |
Cl2—C8—C9—C4 | −178.2 (2) | C11—C12—C17—N4 | 6.0 (3) |
C7—C8—C9—C10 | 179.6 (2) | C13—C12—C17—C16 | 0.9 (3) |
Cl2—C8—C9—C10 | 1.4 (3) | C11—C12—C17—C16 | −175.2 (2) |
N1—C4—C9—C8 | 179.8 (2) | C15—C16—C17—N4 | 179.1 (2) |
C5—C4—C9—C8 | −0.6 (3) | C20—C16—C17—N4 | −0.7 (3) |
N1—C4—C9—C10 | 0.2 (3) | C15—C16—C17—C12 | 0.4 (3) |
C5—C4—C9—C10 | 179.8 (2) | C20—C16—C17—C12 | −179.4 (2) |
N3—N2—C10—O1 | 0.3 (3) | C17—N4—C18—C19 | −1.2 (3) |
N3—N2—C10—C9 | 176.2 (2) | N4—C18—C19—C20 | −0.4 (4) |
C11—O1—C10—N2 | 0.3 (2) | N4—C18—C19—Cl4 | 179.8 (2) |
C11—O1—C10—C9 | −176.2 (2) | C18—C19—C20—C16 | 1.5 (3) |
C8—C9—C10—N2 | −121.9 (3) | Cl4—C19—C20—C16 | −178.7 (2) |
C4—C9—C10—N2 | 57.7 (3) | C15—C16—C20—C19 | 179.2 (2) |
C8—C9—C10—O1 | 53.7 (3) | C17—C16—C20—C19 | −1.0 (3) |
C4—C9—C10—O1 | −126.7 (2) |