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The multiple-bond character of the C—C bond connecting the pyridine and benzoxazole ring systems results in an overall planarity of the central aromatic part of the title compound, C
20H
24N
2O. The crystal structure is stabilized by intermolecular C—H
N close contacts, linking molecules into layers.
Supporting information
CCDC reference: 651379
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.002 Å
- R factor = 0.041
- wR factor = 0.106
- Data-to-parameter ratio = 14.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10 .. N1 .. 2.65 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12 .. N2 .. 2.69 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H19A .. N1 .. 2.66 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 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
0 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
3 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Johnson & Burnett, 1996); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
5,7-Di-
tert-butyl-2-(2-pyridyl)benzo[
d]oxazole
top
Crystal data top
C20H24N2O | F(000) = 664 |
Mr = 308.41 | Dx = 1.178 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2375 reflections |
a = 9.7224 (13) Å | θ = 2.2–26.9° |
b = 6.0174 (8) Å | µ = 0.07 mm−1 |
c = 30.103 (4) Å | T = 120 K |
β = 99.019 (13)° | Prism, colorless |
V = 1739.4 (4) Å3 | 0.50 × 0.30 × 0.20 mm |
Z = 4 | |
Data collection top
Kuma KM-4-Plus CCD diffractometer | 2403 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.030 |
Enhance (Oxford Diffraction) monochromator | θmax = 25.0°, θmin = 3.2° |
Detector resolution: 16.3 pixels mm-1 | h = −11→10 |
rotation method, ω scans | k = −7→5 |
8261 measured reflections | l = −35→33 |
3066 independent reflections | |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.05P)2 + 0.5P] where P = (Fo2 + 2Fc2)/3 |
3066 reflections | (Δ/σ)max = 0.001 |
214 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.55083 (10) | 0.21006 (18) | 0.66155 (4) | 0.0219 (3) | |
N1 | 0.34649 (13) | 0.2561 (2) | 0.68716 (4) | 0.0240 (3) | |
N2 | 0.61057 (13) | −0.1691 (2) | 0.70865 (5) | 0.0243 (3) | |
C1 | 0.52536 (16) | 0.5129 (3) | 0.60447 (5) | 0.0205 (4) | |
C2 | 0.42763 (16) | 0.6707 (3) | 0.58642 (5) | 0.0214 (4) | |
H2 | 0.4502 | 0.7624 | 0.5629 | 0.026* | |
C3 | 0.29714 (16) | 0.7043 (3) | 0.60056 (5) | 0.0205 (4) | |
C4 | 0.26295 (16) | 0.5762 (3) | 0.63556 (5) | 0.0230 (4) | |
H4 | 0.1771 | 0.5969 | 0.6464 | 0.028* | |
C5 | 0.35775 (16) | 0.4168 (3) | 0.65436 (5) | 0.0214 (4) | |
C6 | 0.48332 (16) | 0.3884 (3) | 0.63856 (5) | 0.0198 (4) | |
C7 | 0.45995 (16) | 0.1407 (3) | 0.68930 (5) | 0.0223 (4) | |
C8 | 0.49814 (16) | −0.0562 (3) | 0.71690 (5) | 0.0217 (4) | |
C9 | 0.41854 (17) | −0.1187 (3) | 0.74923 (6) | 0.0295 (4) | |
H9 | 0.3389 | −0.0352 | 0.7537 | 0.035* | |
C10 | 0.45767 (18) | −0.3048 (3) | 0.77479 (6) | 0.0333 (5) | |
H10 | 0.4053 | −0.3521 | 0.7972 | 0.040* | |
C11 | 0.57415 (18) | −0.4214 (3) | 0.76733 (6) | 0.0290 (4) | |
H11 | 0.6045 | −0.5487 | 0.7848 | 0.035* | |
C12 | 0.64538 (17) | −0.3487 (3) | 0.73396 (6) | 0.0265 (4) | |
H12 | 0.7243 | −0.4318 | 0.7286 | 0.032* | |
C13 | 0.66507 (16) | 0.4738 (3) | 0.58839 (6) | 0.0223 (4) | |
C14 | 0.67180 (18) | 0.2330 (3) | 0.57234 (6) | 0.0289 (4) | |
H14A | 0.5956 | 0.2058 | 0.5475 | 0.043* | |
H14B | 0.6630 | 0.1318 | 0.5972 | 0.043* | |
H14C | 0.7611 | 0.2073 | 0.5620 | 0.043* | |
C15 | 0.78409 (17) | 0.5148 (3) | 0.62767 (6) | 0.0317 (4) | |
H15A | 0.8738 | 0.4954 | 0.6172 | 0.048* | |
H15B | 0.7768 | 0.4087 | 0.6519 | 0.048* | |
H15C | 0.7774 | 0.6666 | 0.6389 | 0.048* | |
C16 | 0.68513 (17) | 0.6263 (3) | 0.54932 (6) | 0.0278 (4) | |
H16A | 0.7760 | 0.5969 | 0.5403 | 0.042* | |
H16B | 0.6809 | 0.7817 | 0.5588 | 0.042* | |
H16C | 0.6113 | 0.5982 | 0.5238 | 0.042* | |
C17 | 0.18928 (16) | 0.8620 (3) | 0.57439 (5) | 0.0230 (4) | |
C18 | 0.25739 (18) | 1.0497 (3) | 0.55127 (6) | 0.0279 (4) | |
H18A | 0.1856 | 1.1542 | 0.5377 | 0.042* | |
H18B | 0.3054 | 0.9872 | 0.5278 | 0.042* | |
H18C | 0.3247 | 1.1277 | 0.5735 | 0.042* | |
C19 | 0.09573 (17) | 0.9680 (3) | 0.60498 (6) | 0.0306 (4) | |
H19A | 0.1534 | 1.0477 | 0.6295 | 0.046* | |
H19B | 0.0425 | 0.8518 | 0.6175 | 0.046* | |
H19C | 0.0314 | 1.0724 | 0.5875 | 0.046* | |
C20 | 0.09854 (18) | 0.7225 (3) | 0.53810 (6) | 0.0320 (4) | |
H20A | 0.0275 | 0.8177 | 0.5209 | 0.048* | |
H20B | 0.0532 | 0.6029 | 0.5525 | 0.048* | |
H20C | 0.1573 | 0.6581 | 0.5178 | 0.048* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0196 (6) | 0.0240 (6) | 0.0224 (6) | −0.0001 (5) | 0.0040 (5) | 0.0030 (5) |
N1 | 0.0206 (7) | 0.0286 (8) | 0.0229 (7) | −0.0001 (6) | 0.0037 (6) | 0.0031 (6) |
N2 | 0.0221 (7) | 0.0254 (8) | 0.0246 (8) | −0.0014 (6) | 0.0017 (6) | −0.0004 (6) |
C1 | 0.0202 (8) | 0.0194 (9) | 0.0218 (9) | −0.0032 (7) | 0.0027 (7) | −0.0038 (7) |
C2 | 0.0224 (8) | 0.0208 (9) | 0.0210 (8) | −0.0022 (7) | 0.0032 (7) | −0.0008 (7) |
C3 | 0.0195 (8) | 0.0204 (9) | 0.0212 (8) | −0.0006 (6) | 0.0018 (6) | −0.0034 (7) |
C4 | 0.0173 (8) | 0.0294 (10) | 0.0227 (9) | 0.0002 (7) | 0.0047 (7) | −0.0022 (8) |
C5 | 0.0203 (8) | 0.0245 (9) | 0.0192 (8) | −0.0028 (7) | 0.0029 (7) | −0.0014 (7) |
C6 | 0.0187 (8) | 0.0187 (9) | 0.0212 (9) | −0.0001 (6) | 0.0006 (7) | −0.0012 (7) |
C7 | 0.0196 (8) | 0.0277 (10) | 0.0203 (9) | −0.0047 (7) | 0.0048 (7) | −0.0005 (7) |
C8 | 0.0192 (8) | 0.0251 (9) | 0.0196 (8) | −0.0032 (7) | −0.0005 (7) | −0.0009 (7) |
C9 | 0.0249 (9) | 0.0375 (11) | 0.0272 (10) | 0.0052 (8) | 0.0078 (8) | 0.0064 (8) |
C10 | 0.0309 (10) | 0.0421 (12) | 0.0283 (10) | 0.0026 (8) | 0.0092 (8) | 0.0114 (9) |
C11 | 0.0302 (9) | 0.0301 (10) | 0.0258 (10) | 0.0025 (8) | 0.0020 (8) | 0.0073 (8) |
C12 | 0.0255 (9) | 0.0279 (10) | 0.0255 (9) | 0.0019 (8) | 0.0023 (7) | 0.0022 (8) |
C13 | 0.0198 (8) | 0.0216 (9) | 0.0267 (9) | −0.0001 (7) | 0.0071 (7) | 0.0001 (7) |
C14 | 0.0296 (10) | 0.0259 (10) | 0.0340 (10) | 0.0010 (7) | 0.0133 (8) | 0.0000 (8) |
C15 | 0.0199 (9) | 0.0407 (12) | 0.0353 (10) | −0.0028 (8) | 0.0071 (8) | −0.0003 (9) |
C16 | 0.0260 (9) | 0.0260 (10) | 0.0338 (10) | −0.0001 (7) | 0.0126 (8) | 0.0012 (8) |
C17 | 0.0203 (8) | 0.0234 (9) | 0.0247 (9) | 0.0011 (7) | 0.0017 (7) | −0.0008 (7) |
C18 | 0.0253 (9) | 0.0279 (10) | 0.0300 (10) | 0.0024 (7) | 0.0024 (7) | 0.0033 (8) |
C19 | 0.0255 (9) | 0.0305 (10) | 0.0361 (11) | 0.0061 (8) | 0.0058 (8) | 0.0014 (8) |
C20 | 0.0290 (9) | 0.0320 (11) | 0.0321 (10) | −0.0002 (8) | −0.0043 (8) | −0.0016 (8) |
Geometric parameters (Å, º) top
O1—C7 | 1.3727 (19) | C13—C16 | 1.528 (2) |
O1—C6 | 1.3852 (19) | C13—C14 | 1.532 (2) |
N1—C7 | 1.296 (2) | C13—C15 | 1.539 (2) |
N1—C5 | 1.398 (2) | C14—H14A | 0.9800 |
N2—C12 | 1.335 (2) | C14—H14B | 0.9800 |
N2—C8 | 1.343 (2) | C14—H14C | 0.9800 |
C1—C6 | 1.383 (2) | C15—H15A | 0.9800 |
C1—C2 | 1.392 (2) | C15—H15B | 0.9800 |
C1—C13 | 1.530 (2) | C15—H15C | 0.9800 |
C2—C3 | 1.415 (2) | C16—H16A | 0.9800 |
C2—H2 | 0.9500 | C16—H16B | 0.9800 |
C3—C4 | 1.387 (2) | C16—H16C | 0.9800 |
C3—C17 | 1.537 (2) | C17—C18 | 1.531 (2) |
C4—C5 | 1.388 (2) | C17—C19 | 1.531 (2) |
C4—H4 | 0.9500 | C17—C20 | 1.541 (2) |
C5—C6 | 1.388 (2) | C18—H18A | 0.9800 |
C7—C8 | 1.461 (2) | C18—H18B | 0.9800 |
C8—C9 | 1.387 (2) | C18—H18C | 0.9800 |
C9—C10 | 1.378 (3) | C19—H19A | 0.9800 |
C9—H9 | 0.9500 | C19—H19B | 0.9800 |
C10—C11 | 1.380 (2) | C19—H19C | 0.9800 |
C10—H10 | 0.9500 | C20—H20A | 0.9800 |
C11—C12 | 1.378 (2) | C20—H20B | 0.9800 |
C11—H11 | 0.9500 | C20—H20C | 0.9800 |
C12—H12 | 0.9500 | | |
| | | |
C7—O1—C6 | 103.87 (12) | C14—C13—C15 | 109.26 (14) |
C7—N1—C5 | 104.20 (13) | C13—C14—H14A | 109.5 |
C12—N2—C8 | 116.42 (14) | C13—C14—H14B | 109.5 |
C6—C1—C2 | 113.33 (14) | H14A—C14—H14B | 109.5 |
C6—C1—C13 | 122.13 (14) | C13—C14—H14C | 109.5 |
C2—C1—C13 | 124.53 (15) | H14A—C14—H14C | 109.5 |
C1—C2—C3 | 124.71 (15) | H14B—C14—H14C | 109.5 |
C1—C2—H2 | 117.6 | C13—C15—H15A | 109.5 |
C3—C2—H2 | 117.6 | C13—C15—H15B | 109.5 |
C4—C3—C2 | 118.82 (15) | H15A—C15—H15B | 109.5 |
C4—C3—C17 | 120.46 (14) | C13—C15—H15C | 109.5 |
C2—C3—C17 | 120.40 (14) | H15A—C15—H15C | 109.5 |
C3—C4—C5 | 118.08 (15) | H15B—C15—H15C | 109.5 |
C3—C4—H4 | 121.0 | C13—C16—H16A | 109.5 |
C5—C4—H4 | 121.0 | C13—C16—H16B | 109.5 |
C4—C5—C6 | 120.59 (15) | H16A—C16—H16B | 109.5 |
C4—C5—N1 | 130.18 (15) | C13—C16—H16C | 109.5 |
C6—C5—N1 | 109.09 (14) | H16A—C16—H16C | 109.5 |
C1—C6—O1 | 128.18 (14) | H16B—C16—H16C | 109.5 |
C1—C6—C5 | 124.44 (15) | C18—C17—C19 | 107.81 (14) |
O1—C6—C5 | 107.31 (13) | C18—C17—C3 | 112.31 (13) |
N1—C7—O1 | 115.51 (14) | C19—C17—C3 | 111.77 (13) |
N1—C7—C8 | 126.94 (15) | C18—C17—C20 | 108.68 (14) |
O1—C7—C8 | 117.52 (14) | C19—C17—C20 | 108.98 (14) |
N2—C8—C9 | 123.53 (16) | C3—C17—C20 | 107.22 (13) |
N2—C8—C7 | 116.53 (14) | C17—C18—H18A | 109.5 |
C9—C8—C7 | 119.93 (15) | C17—C18—H18B | 109.5 |
C10—C9—C8 | 118.47 (16) | H18A—C18—H18B | 109.5 |
C10—C9—H9 | 120.8 | C17—C18—H18C | 109.5 |
C8—C9—H9 | 120.8 | H18A—C18—H18C | 109.5 |
C9—C10—C11 | 118.94 (17) | H18B—C18—H18C | 109.5 |
C9—C10—H10 | 120.5 | C17—C19—H19A | 109.5 |
C11—C10—H10 | 120.5 | C17—C19—H19B | 109.5 |
C12—C11—C10 | 118.46 (17) | H19A—C19—H19B | 109.5 |
C12—C11—H11 | 120.8 | C17—C19—H19C | 109.5 |
C10—C11—H11 | 120.8 | H19A—C19—H19C | 109.5 |
N2—C12—C11 | 124.16 (16) | H19B—C19—H19C | 109.5 |
N2—C12—H12 | 117.9 | C17—C20—H20A | 109.5 |
C11—C12—H12 | 117.9 | C17—C20—H20B | 109.5 |
C16—C13—C1 | 112.20 (13) | H20A—C20—H20B | 109.5 |
C16—C13—C14 | 107.97 (14) | C17—C20—H20C | 109.5 |
C1—C13—C14 | 109.22 (13) | H20A—C20—H20C | 109.5 |
C16—C13—C15 | 108.87 (14) | H20B—C20—H20C | 109.5 |
C1—C13—C15 | 109.27 (13) | | |
| | | |
C6—C1—C2—C3 | −0.3 (2) | C12—N2—C8—C9 | −0.8 (2) |
C13—C1—C2—C3 | 178.64 (15) | C12—N2—C8—C7 | 179.91 (14) |
C1—C2—C3—C4 | 1.5 (2) | N1—C7—C8—N2 | 170.00 (16) |
C1—C2—C3—C17 | −172.09 (15) | O1—C7—C8—N2 | −8.1 (2) |
C2—C3—C4—C5 | −1.5 (2) | N1—C7—C8—C9 | −9.3 (3) |
C17—C3—C4—C5 | 172.10 (14) | O1—C7—C8—C9 | 172.60 (15) |
C3—C4—C5—C6 | 0.4 (2) | N2—C8—C9—C10 | 1.0 (3) |
C3—C4—C5—N1 | −174.78 (16) | C7—C8—C9—C10 | −179.79 (16) |
C7—N1—C5—C4 | 174.84 (17) | C8—C9—C10—C11 | 0.1 (3) |
C7—N1—C5—C6 | −0.74 (18) | C9—C10—C11—C12 | −1.1 (3) |
C2—C1—C6—O1 | 175.54 (14) | C8—N2—C12—C11 | −0.4 (2) |
C13—C1—C6—O1 | −3.4 (3) | C10—C11—C12—N2 | 1.3 (3) |
C2—C1—C6—C5 | −1.0 (2) | C6—C1—C13—C16 | 177.90 (15) |
C13—C1—C6—C5 | −179.90 (15) | C2—C1—C13—C16 | −0.9 (2) |
C7—O1—C6—C1 | −176.13 (16) | C6—C1—C13—C14 | 58.2 (2) |
C7—O1—C6—C5 | 0.85 (16) | C2—C1—C13—C14 | −120.58 (17) |
C4—C5—C6—C1 | 0.9 (3) | C6—C1—C13—C15 | −61.2 (2) |
N1—C5—C6—C1 | 177.03 (15) | C2—C1—C13—C15 | 119.95 (17) |
C4—C5—C6—O1 | −176.18 (14) | C4—C3—C17—C18 | 157.19 (15) |
N1—C5—C6—O1 | −0.10 (18) | C2—C3—C17—C18 | −29.3 (2) |
C5—N1—C7—O1 | 1.39 (19) | C4—C3—C17—C19 | 35.9 (2) |
C5—N1—C7—C8 | −176.74 (15) | C2—C3—C17—C19 | −150.65 (15) |
C6—O1—C7—N1 | −1.46 (18) | C4—C3—C17—C20 | −83.50 (19) |
C6—O1—C7—C8 | 176.85 (13) | C2—C3—C17—C20 | 89.99 (18) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···N1i | 0.95 | 2.65 | 3.355 (2) | 132 |
C12—H12···N2ii | 0.95 | 2.69 | 3.323 (2) | 125 |
C19—H19A···N1iii | 0.98 | 2.66 | 3.630 (2) | 170 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2; (ii) −x+3/2, y−1/2, −z+3/2; (iii) x, y+1, z. |
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