In the molecule of the title compound, C
18H
12FNO
2, the oxazine ring is not planar and has a flattened boat conformation The dihedral angle between the benzene ring and the naphthalene system is 78.4 (3)°. In the crystal structure, intermolecular N—H
O hydrogen bonds link the molecules into dimers, which may be effective in the stabilization of the structure.
Supporting information
CCDC reference: 640370
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.050
- wR factor = 0.118
- Data-to-parameter ratio = 12.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for C12 - C13 .. 5.12 su
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C3
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
0 ALERT type 5 Informative message, check
Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2005); 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).
1-(4-Fluorophenyl)-2,3-dihydro-1
H-naphtho[1,2-
e][1,3]oxazin-3-one
top
Crystal data top
C18H12FNO2 | F(000) = 608 |
Mr = 293.29 | Dx = 1.35 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2000 reflections |
a = 13.319 (4) Å | θ = 1.8–26.8° |
b = 6.3601 (15) Å | µ = 0.10 mm−1 |
c = 17.331 (6) Å | T = 294 K |
β = 100.55 (3)° | Plate, colorless |
V = 1443.4 (8) Å3 | 0.5 × 0.2 × 0.1 mm |
Z = 4 | |
Data collection top
Stoe IPDSII diffractometer | Rint = 0.038 |
rotation method scans | θmax = 26.8°, θmin = 1.8° |
7507 measured reflections | h = −16→16 |
3035 independent reflections | k = −8→7 |
2291 reflections with I > 2σ(I) | l = −21→16 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.05 | w = 1/[σ2(Fo2) + (0.0428P)2 + 0.268P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.118 | (Δ/σ)max = 0.002 |
S = 1.13 | Δρmax = 0.13 e Å−3 |
3035 reflections | Δρmin = −0.15 e Å−3 |
247 parameters | |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
F1 | 0.92485 (9) | 0.1807 (3) | 0.87148 (11) | 0.1179 (6) | |
O1 | 0.40249 (9) | 0.04298 (19) | 0.92693 (7) | 0.0558 (3) | |
O2 | 0.42599 (10) | 0.2798 (2) | 1.02123 (8) | 0.0631 (4) | |
N1 | 0.47282 (11) | 0.3643 (2) | 0.90620 (9) | 0.0521 (4) | |
H1B | 0.5019 (14) | 0.481 (3) | 0.9289 (11) | 0.060 (5)* | |
C1 | 0.65897 (14) | 0.0919 (3) | 0.87560 (12) | 0.0602 (5) | |
H1 | 0.6156 (16) | −0.021 (4) | 0.8908 (13) | 0.080 (7)* | |
C2 | 0.76388 (15) | 0.0615 (4) | 0.88668 (15) | 0.0747 (6) | |
H2 | 0.7933 (17) | −0.062 (4) | 0.9144 (14) | 0.086 (7)* | |
C3 | 0.82210 (14) | 0.2131 (4) | 0.86147 (13) | 0.0748 (6) | |
C4 | 0.78253 (17) | 0.3921 (4) | 0.82598 (15) | 0.0789 (7) | |
H4 | 0.823 (2) | 0.497 (4) | 0.8084 (15) | 0.103 (8)* | |
C5 | 0.67741 (15) | 0.4224 (4) | 0.81567 (12) | 0.0635 (5) | |
H5 | 0.6441 (17) | 0.552 (4) | 0.7917 (14) | 0.085 (7)* | |
C6 | 0.61523 (12) | 0.2717 (3) | 0.84002 (9) | 0.0467 (4) | |
C7 | 0.50028 (12) | 0.3080 (3) | 0.83083 (10) | 0.0469 (4) | |
H7 | 0.4812 (13) | 0.430 (3) | 0.7962 (10) | 0.051 (5)* | |
C8 | 0.43795 (11) | 0.1211 (3) | 0.79805 (10) | 0.0475 (4) | |
C9 | 0.41978 (12) | 0.0707 (3) | 0.71654 (11) | 0.0533 (4) | |
C10 | 0.45185 (16) | 0.2016 (4) | 0.65971 (12) | 0.0668 (5) | |
H10 | 0.4899 (15) | 0.328 (4) | 0.6740 (12) | 0.068 (6)* | |
C11 | 0.4267 (2) | 0.1534 (5) | 0.58144 (14) | 0.0857 (7) | |
H11 | 0.4514 (18) | 0.250 (4) | 0.5457 (15) | 0.088 (7)* | |
C12 | 0.3702 (2) | −0.0283 (5) | 0.55674 (17) | 0.0915 (8) | |
H12 | 0.352 (2) | −0.052 (5) | 0.5010 (19) | 0.122 (10)* | |
C13 | 0.34062 (17) | −0.1594 (4) | 0.60960 (15) | 0.0772 (6) | |
H13 | 0.3005 (19) | −0.295 (4) | 0.5939 (15) | 0.104 (8)* | |
C14 | 0.36381 (12) | −0.1153 (3) | 0.69086 (12) | 0.0600 (5) | |
C15 | 0.33022 (13) | −0.2461 (3) | 0.74723 (14) | 0.0629 (5) | |
H15 | 0.2938 (15) | −0.375 (3) | 0.7316 (12) | 0.069 (6)* | |
C16 | 0.34458 (13) | −0.1928 (3) | 0.82406 (13) | 0.0572 (5) | |
H16 | 0.3178 (15) | −0.276 (3) | 0.8639 (12) | 0.072 (6)* | |
C17 | 0.39713 (11) | −0.0054 (3) | 0.84824 (11) | 0.0487 (4) | |
C18 | 0.43550 (12) | 0.2358 (3) | 0.95441 (11) | 0.0497 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F1 | 0.0445 (6) | 0.1531 (16) | 0.1577 (15) | −0.0099 (8) | 0.0228 (7) | −0.0317 (13) |
O1 | 0.0609 (7) | 0.0467 (7) | 0.0606 (8) | −0.0077 (5) | 0.0130 (6) | 0.0076 (6) |
O2 | 0.0753 (8) | 0.0598 (8) | 0.0597 (8) | −0.0090 (6) | 0.0270 (6) | 0.0030 (7) |
N1 | 0.0598 (8) | 0.0428 (8) | 0.0579 (9) | −0.0060 (7) | 0.0218 (7) | −0.0005 (7) |
C1 | 0.0491 (9) | 0.0620 (12) | 0.0699 (12) | −0.0030 (9) | 0.0118 (8) | 0.0123 (10) |
C2 | 0.0539 (11) | 0.0812 (16) | 0.0865 (16) | 0.0065 (11) | 0.0058 (10) | 0.0055 (13) |
C3 | 0.0437 (9) | 0.1029 (18) | 0.0792 (14) | −0.0128 (11) | 0.0148 (9) | −0.0207 (14) |
C4 | 0.0642 (12) | 0.0934 (18) | 0.0850 (16) | −0.0319 (13) | 0.0291 (11) | −0.0057 (14) |
C5 | 0.0633 (11) | 0.0624 (12) | 0.0674 (13) | −0.0185 (10) | 0.0192 (9) | 0.0050 (10) |
C6 | 0.0475 (8) | 0.0513 (9) | 0.0423 (8) | −0.0080 (7) | 0.0112 (6) | 0.0002 (7) |
C7 | 0.0485 (8) | 0.0425 (9) | 0.0504 (9) | −0.0009 (7) | 0.0107 (7) | 0.0054 (7) |
C8 | 0.0371 (7) | 0.0459 (9) | 0.0581 (10) | 0.0021 (7) | 0.0052 (7) | 0.0024 (8) |
C9 | 0.0396 (8) | 0.0585 (10) | 0.0601 (11) | 0.0066 (7) | 0.0047 (7) | −0.0028 (9) |
C10 | 0.0633 (11) | 0.0788 (14) | 0.0581 (12) | −0.0019 (11) | 0.0105 (9) | −0.0013 (11) |
C11 | 0.0913 (16) | 0.105 (2) | 0.0604 (14) | −0.0021 (15) | 0.0130 (12) | 0.0024 (14) |
C12 | 0.0879 (16) | 0.117 (2) | 0.0643 (15) | 0.0008 (16) | −0.0004 (13) | −0.0234 (16) |
C13 | 0.0620 (12) | 0.0877 (17) | 0.0771 (15) | 0.0001 (12) | −0.0003 (10) | −0.0211 (13) |
C14 | 0.0394 (8) | 0.0628 (12) | 0.0737 (13) | 0.0052 (8) | −0.0006 (8) | −0.0133 (10) |
C15 | 0.0407 (8) | 0.0519 (11) | 0.0921 (16) | −0.0019 (8) | 0.0017 (9) | −0.0088 (10) |
C16 | 0.0429 (8) | 0.0475 (10) | 0.0790 (14) | −0.0015 (7) | 0.0050 (8) | 0.0034 (10) |
C17 | 0.0385 (7) | 0.0449 (9) | 0.0613 (11) | 0.0032 (7) | 0.0051 (7) | 0.0043 (8) |
C18 | 0.0468 (8) | 0.0433 (9) | 0.0603 (11) | 0.0006 (7) | 0.0133 (7) | 0.0065 (8) |
Geometric parameters (Å, º) top
C1—C6 | 1.377 (3) | C10—C11 | 1.371 (3) |
C1—C2 | 1.389 (3) | C10—H10 | 0.96 (2) |
C1—H1 | 0.99 (2) | C11—C12 | 1.402 (4) |
C2—C3 | 1.359 (3) | C11—H11 | 0.97 (3) |
C2—H2 | 0.96 (3) | C12—C13 | 1.350 (4) |
C3—C4 | 1.354 (4) | C12—H12 | 0.96 (3) |
C3—F1 | 1.363 (2) | C13—C14 | 1.413 (3) |
C4—C5 | 1.392 (3) | C13—H13 | 1.02 (3) |
C4—H4 | 0.94 (3) | C14—C15 | 1.416 (3) |
C5—C6 | 1.382 (2) | C15—C16 | 1.353 (3) |
C5—H5 | 0.99 (2) | C15—H15 | 0.97 (2) |
C6—C7 | 1.528 (2) | C16—C17 | 1.407 (2) |
C7—N1 | 1.464 (2) | C16—H16 | 0.99 (2) |
C7—C8 | 1.501 (2) | C17—O1 | 1.387 (2) |
C7—H7 | 0.986 (19) | C18—O2 | 1.220 (2) |
C8—C17 | 1.369 (2) | C18—N1 | 1.328 (2) |
C8—C9 | 1.426 (3) | C18—O1 | 1.359 (2) |
C9—C10 | 1.414 (3) | N1—H1B | 0.90 (2) |
C9—C14 | 1.425 (3) | | |
| | | |
C6—C1—C2 | 120.69 (19) | C11—C10—H10 | 117.7 (13) |
C6—C1—H1 | 120.3 (13) | C9—C10—H10 | 121.8 (13) |
C2—C1—H1 | 118.9 (13) | C10—C11—C12 | 120.4 (3) |
C3—C2—C1 | 118.4 (2) | C10—C11—H11 | 116.0 (15) |
C3—C2—H2 | 122.3 (14) | C12—C11—H11 | 123.6 (15) |
C1—C2—H2 | 119.3 (14) | C13—C12—C11 | 120.6 (2) |
C4—C3—C2 | 123.05 (19) | C13—C12—H12 | 122.3 (19) |
C4—C3—F1 | 118.9 (2) | C11—C12—H12 | 117.1 (19) |
C2—C3—F1 | 118.0 (2) | C12—C13—C14 | 121.1 (2) |
C3—C4—C5 | 118.2 (2) | C12—C13—H13 | 122.9 (15) |
C3—C4—H4 | 122.6 (16) | C14—C13—H13 | 116.1 (15) |
C5—C4—H4 | 119.2 (16) | C13—C14—C15 | 122.1 (2) |
C6—C5—C4 | 120.6 (2) | C13—C14—C9 | 118.8 (2) |
C6—C5—H5 | 117.3 (14) | C15—C14—C9 | 119.01 (18) |
C4—C5—H5 | 122.1 (14) | C16—C15—C14 | 121.74 (19) |
C1—C6—C5 | 118.99 (17) | C16—C15—H15 | 117.5 (12) |
C1—C6—C7 | 120.41 (15) | C14—C15—H15 | 120.7 (12) |
C5—C6—C7 | 120.55 (17) | C15—C16—C17 | 118.57 (19) |
N1—C7—C8 | 108.66 (14) | C15—C16—H16 | 123.3 (13) |
N1—C7—C6 | 110.69 (14) | C17—C16—H16 | 118.1 (12) |
C8—C7—C6 | 113.21 (14) | C8—C17—O1 | 122.67 (15) |
N1—C7—H7 | 105.7 (10) | C8—C17—C16 | 122.87 (18) |
C8—C7—H7 | 109.3 (10) | O1—C17—C16 | 114.45 (16) |
C6—C7—H7 | 108.9 (10) | O2—C18—N1 | 124.88 (17) |
C17—C8—C9 | 118.84 (16) | O2—C18—O1 | 117.14 (15) |
C17—C8—C7 | 118.79 (16) | N1—C18—O1 | 117.95 (16) |
C9—C8—C7 | 122.37 (16) | C18—N1—C7 | 126.48 (16) |
C10—C9—C14 | 118.58 (19) | C18—N1—H1B | 114.6 (13) |
C10—C9—C8 | 122.65 (18) | C7—N1—H1B | 115.8 (13) |
C14—C9—C8 | 118.72 (17) | C18—O1—C17 | 119.97 (13) |
C11—C10—C9 | 120.5 (2) | | |
| | | |
C6—C1—C2—C3 | −0.1 (3) | C10—C11—C12—C13 | −0.6 (4) |
C1—C2—C3—C4 | −0.1 (4) | C11—C12—C13—C14 | 1.3 (4) |
C1—C2—C3—F1 | −179.0 (2) | C12—C13—C14—C15 | 177.5 (2) |
C2—C3—C4—C5 | 0.7 (4) | C12—C13—C14—C9 | −0.3 (3) |
F1—C3—C4—C5 | 179.6 (2) | C10—C9—C14—C13 | −1.4 (3) |
C3—C4—C5—C6 | −1.0 (3) | C8—C9—C14—C13 | 176.40 (16) |
C2—C1—C6—C5 | −0.3 (3) | C10—C9—C14—C15 | −179.21 (16) |
C2—C1—C6—C7 | −177.66 (19) | C8—C9—C14—C15 | −1.4 (2) |
C4—C5—C6—C1 | 0.8 (3) | C13—C14—C15—C16 | −173.80 (18) |
C4—C5—C6—C7 | 178.21 (19) | C9—C14—C15—C16 | 4.0 (3) |
C1—C6—C7—N1 | 74.1 (2) | C14—C15—C16—C17 | −2.0 (3) |
C5—C6—C7—N1 | −103.27 (19) | C9—C8—C17—O1 | −173.57 (14) |
C1—C6—C7—C8 | −48.2 (2) | C7—C8—C17—O1 | 6.5 (2) |
C5—C6—C7—C8 | 134.45 (18) | C9—C8—C17—C16 | 5.1 (2) |
N1—C7—C8—C17 | −21.8 (2) | C7—C8—C17—C16 | −174.84 (15) |
C6—C7—C8—C17 | 101.62 (17) | C15—C16—C17—C8 | −2.7 (2) |
N1—C7—C8—C9 | 158.23 (14) | C15—C16—C17—O1 | 176.10 (15) |
C6—C7—C8—C9 | −78.36 (19) | O2—C18—N1—C7 | 169.77 (16) |
C17—C8—C9—C10 | 174.74 (16) | O1—C18—N1—C7 | −12.3 (2) |
C7—C8—C9—C10 | −5.3 (3) | C8—C7—N1—C18 | 26.1 (2) |
C17—C8—C9—C14 | −2.9 (2) | C6—C7—N1—C18 | −98.77 (19) |
C7—C8—C9—C14 | 177.05 (15) | O2—C18—O1—C17 | 170.55 (14) |
C14—C9—C10—C11 | 2.0 (3) | N1—C18—O1—C17 | −7.6 (2) |
C8—C9—C10—C11 | −175.63 (19) | C8—C17—O1—C18 | 10.0 (2) |
C9—C10—C11—C12 | −1.1 (4) | C16—C17—O1—C18 | −168.77 (14) |