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In the mol­ecule of the title compound, C18H12FNO2, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680700829X/hk2207sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680700829X/hk2207Isup2.hkl
Contains datablock I

CCDC reference: 640370

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](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

Computing details top

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-1H-naphtho[1,2-e][1,3]oxazin-3-one top
Crystal data top
C18H12FNO2F(000) = 608
Mr = 293.29Dx = 1.35 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2000 reflections
a = 13.319 (4) Åθ = 1.8–26.8°
b = 6.3601 (15) ŵ = 0.10 mm1
c = 17.331 (6) ÅT = 294 K
β = 100.55 (3)°Plate, colorless
V = 1443.4 (8) Å30.5 × 0.2 × 0.1 mm
Z = 4
Data collection top
Stoe IPDSII
diffractometer
Rint = 0.038
rotation method scansθmax = 26.8°, θmin = 1.8°
7507 measured reflectionsh = 1616
3035 independent reflectionsk = 87
2291 reflections with I > 2σ(I)l = 2116
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullAll 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 = 1.13Δρmax = 0.13 e Å3
3035 reflectionsΔρmin = 0.15 e Å3
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
xyzUiso*/Ueq
F10.92485 (9)0.1807 (3)0.87148 (11)0.1179 (6)
O10.40249 (9)0.04298 (19)0.92693 (7)0.0558 (3)
O20.42599 (10)0.2798 (2)1.02123 (8)0.0631 (4)
N10.47282 (11)0.3643 (2)0.90620 (9)0.0521 (4)
H1B0.5019 (14)0.481 (3)0.9289 (11)0.060 (5)*
C10.65897 (14)0.0919 (3)0.87560 (12)0.0602 (5)
H10.6156 (16)0.021 (4)0.8908 (13)0.080 (7)*
C20.76388 (15)0.0615 (4)0.88668 (15)0.0747 (6)
H20.7933 (17)0.062 (4)0.9144 (14)0.086 (7)*
C30.82210 (14)0.2131 (4)0.86147 (13)0.0748 (6)
C40.78253 (17)0.3921 (4)0.82598 (15)0.0789 (7)
H40.823 (2)0.497 (4)0.8084 (15)0.103 (8)*
C50.67741 (15)0.4224 (4)0.81567 (12)0.0635 (5)
H50.6441 (17)0.552 (4)0.7917 (14)0.085 (7)*
C60.61523 (12)0.2717 (3)0.84002 (9)0.0467 (4)
C70.50028 (12)0.3080 (3)0.83083 (10)0.0469 (4)
H70.4812 (13)0.430 (3)0.7962 (10)0.051 (5)*
C80.43795 (11)0.1211 (3)0.79805 (10)0.0475 (4)
C90.41978 (12)0.0707 (3)0.71654 (11)0.0533 (4)
C100.45185 (16)0.2016 (4)0.65971 (12)0.0668 (5)
H100.4899 (15)0.328 (4)0.6740 (12)0.068 (6)*
C110.4267 (2)0.1534 (5)0.58144 (14)0.0857 (7)
H110.4514 (18)0.250 (4)0.5457 (15)0.088 (7)*
C120.3702 (2)0.0283 (5)0.55674 (17)0.0915 (8)
H120.352 (2)0.052 (5)0.5010 (19)0.122 (10)*
C130.34062 (17)0.1594 (4)0.60960 (15)0.0772 (6)
H130.3005 (19)0.295 (4)0.5939 (15)0.104 (8)*
C140.36381 (12)0.1153 (3)0.69086 (12)0.0600 (5)
C150.33022 (13)0.2461 (3)0.74723 (14)0.0629 (5)
H150.2938 (15)0.375 (3)0.7316 (12)0.069 (6)*
C160.34458 (13)0.1928 (3)0.82406 (13)0.0572 (5)
H160.3178 (15)0.276 (3)0.8639 (12)0.072 (6)*
C170.39713 (11)0.0054 (3)0.84824 (11)0.0487 (4)
C180.43550 (12)0.2358 (3)0.95441 (11)0.0497 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0445 (6)0.1531 (16)0.1577 (15)0.0099 (8)0.0228 (7)0.0317 (13)
O10.0609 (7)0.0467 (7)0.0606 (8)0.0077 (5)0.0130 (6)0.0076 (6)
O20.0753 (8)0.0598 (8)0.0597 (8)0.0090 (6)0.0270 (6)0.0030 (7)
N10.0598 (8)0.0428 (8)0.0579 (9)0.0060 (7)0.0218 (7)0.0005 (7)
C10.0491 (9)0.0620 (12)0.0699 (12)0.0030 (9)0.0118 (8)0.0123 (10)
C20.0539 (11)0.0812 (16)0.0865 (16)0.0065 (11)0.0058 (10)0.0055 (13)
C30.0437 (9)0.1029 (18)0.0792 (14)0.0128 (11)0.0148 (9)0.0207 (14)
C40.0642 (12)0.0934 (18)0.0850 (16)0.0319 (13)0.0291 (11)0.0057 (14)
C50.0633 (11)0.0624 (12)0.0674 (13)0.0185 (10)0.0192 (9)0.0050 (10)
C60.0475 (8)0.0513 (9)0.0423 (8)0.0080 (7)0.0112 (6)0.0002 (7)
C70.0485 (8)0.0425 (9)0.0504 (9)0.0009 (7)0.0107 (7)0.0054 (7)
C80.0371 (7)0.0459 (9)0.0581 (10)0.0021 (7)0.0052 (7)0.0024 (8)
C90.0396 (8)0.0585 (10)0.0601 (11)0.0066 (7)0.0047 (7)0.0028 (9)
C100.0633 (11)0.0788 (14)0.0581 (12)0.0019 (11)0.0105 (9)0.0013 (11)
C110.0913 (16)0.105 (2)0.0604 (14)0.0021 (15)0.0130 (12)0.0024 (14)
C120.0879 (16)0.117 (2)0.0643 (15)0.0008 (16)0.0004 (13)0.0234 (16)
C130.0620 (12)0.0877 (17)0.0771 (15)0.0001 (12)0.0003 (10)0.0211 (13)
C140.0394 (8)0.0628 (12)0.0737 (13)0.0052 (8)0.0006 (8)0.0133 (10)
C150.0407 (8)0.0519 (11)0.0921 (16)0.0019 (8)0.0017 (9)0.0088 (10)
C160.0429 (8)0.0475 (10)0.0790 (14)0.0015 (7)0.0050 (8)0.0034 (10)
C170.0385 (7)0.0449 (9)0.0613 (11)0.0032 (7)0.0051 (7)0.0043 (8)
C180.0468 (8)0.0433 (9)0.0603 (11)0.0006 (7)0.0133 (7)0.0065 (8)
Geometric parameters (Å, º) top
C1—C61.377 (3)C10—C111.371 (3)
C1—C21.389 (3)C10—H100.96 (2)
C1—H10.99 (2)C11—C121.402 (4)
C2—C31.359 (3)C11—H110.97 (3)
C2—H20.96 (3)C12—C131.350 (4)
C3—C41.354 (4)C12—H120.96 (3)
C3—F11.363 (2)C13—C141.413 (3)
C4—C51.392 (3)C13—H131.02 (3)
C4—H40.94 (3)C14—C151.416 (3)
C5—C61.382 (2)C15—C161.353 (3)
C5—H50.99 (2)C15—H150.97 (2)
C6—C71.528 (2)C16—C171.407 (2)
C7—N11.464 (2)C16—H160.99 (2)
C7—C81.501 (2)C17—O11.387 (2)
C7—H70.986 (19)C18—O21.220 (2)
C8—C171.369 (2)C18—N11.328 (2)
C8—C91.426 (3)C18—O11.359 (2)
C9—C101.414 (3)N1—H1B0.90 (2)
C9—C141.425 (3)
C6—C1—C2120.69 (19)C11—C10—H10117.7 (13)
C6—C1—H1120.3 (13)C9—C10—H10121.8 (13)
C2—C1—H1118.9 (13)C10—C11—C12120.4 (3)
C3—C2—C1118.4 (2)C10—C11—H11116.0 (15)
C3—C2—H2122.3 (14)C12—C11—H11123.6 (15)
C1—C2—H2119.3 (14)C13—C12—C11120.6 (2)
C4—C3—C2123.05 (19)C13—C12—H12122.3 (19)
C4—C3—F1118.9 (2)C11—C12—H12117.1 (19)
C2—C3—F1118.0 (2)C12—C13—C14121.1 (2)
C3—C4—C5118.2 (2)C12—C13—H13122.9 (15)
C3—C4—H4122.6 (16)C14—C13—H13116.1 (15)
C5—C4—H4119.2 (16)C13—C14—C15122.1 (2)
C6—C5—C4120.6 (2)C13—C14—C9118.8 (2)
C6—C5—H5117.3 (14)C15—C14—C9119.01 (18)
C4—C5—H5122.1 (14)C16—C15—C14121.74 (19)
C1—C6—C5118.99 (17)C16—C15—H15117.5 (12)
C1—C6—C7120.41 (15)C14—C15—H15120.7 (12)
C5—C6—C7120.55 (17)C15—C16—C17118.57 (19)
N1—C7—C8108.66 (14)C15—C16—H16123.3 (13)
N1—C7—C6110.69 (14)C17—C16—H16118.1 (12)
C8—C7—C6113.21 (14)C8—C17—O1122.67 (15)
N1—C7—H7105.7 (10)C8—C17—C16122.87 (18)
C8—C7—H7109.3 (10)O1—C17—C16114.45 (16)
C6—C7—H7108.9 (10)O2—C18—N1124.88 (17)
C17—C8—C9118.84 (16)O2—C18—O1117.14 (15)
C17—C8—C7118.79 (16)N1—C18—O1117.95 (16)
C9—C8—C7122.37 (16)C18—N1—C7126.48 (16)
C10—C9—C14118.58 (19)C18—N1—H1B114.6 (13)
C10—C9—C8122.65 (18)C7—N1—H1B115.8 (13)
C14—C9—C8118.72 (17)C18—O1—C17119.97 (13)
C11—C10—C9120.5 (2)
C6—C1—C2—C30.1 (3)C10—C11—C12—C130.6 (4)
C1—C2—C3—C40.1 (4)C11—C12—C13—C141.3 (4)
C1—C2—C3—F1179.0 (2)C12—C13—C14—C15177.5 (2)
C2—C3—C4—C50.7 (4)C12—C13—C14—C90.3 (3)
F1—C3—C4—C5179.6 (2)C10—C9—C14—C131.4 (3)
C3—C4—C5—C61.0 (3)C8—C9—C14—C13176.40 (16)
C2—C1—C6—C50.3 (3)C10—C9—C14—C15179.21 (16)
C2—C1—C6—C7177.66 (19)C8—C9—C14—C151.4 (2)
C4—C5—C6—C10.8 (3)C13—C14—C15—C16173.80 (18)
C4—C5—C6—C7178.21 (19)C9—C14—C15—C164.0 (3)
C1—C6—C7—N174.1 (2)C14—C15—C16—C172.0 (3)
C5—C6—C7—N1103.27 (19)C9—C8—C17—O1173.57 (14)
C1—C6—C7—C848.2 (2)C7—C8—C17—O16.5 (2)
C5—C6—C7—C8134.45 (18)C9—C8—C17—C165.1 (2)
N1—C7—C8—C1721.8 (2)C7—C8—C17—C16174.84 (15)
C6—C7—C8—C17101.62 (17)C15—C16—C17—C82.7 (2)
N1—C7—C8—C9158.23 (14)C15—C16—C17—O1176.10 (15)
C6—C7—C8—C978.36 (19)O2—C18—N1—C7169.77 (16)
C17—C8—C9—C10174.74 (16)O1—C18—N1—C712.3 (2)
C7—C8—C9—C105.3 (3)C8—C7—N1—C1826.1 (2)
C17—C8—C9—C142.9 (2)C6—C7—N1—C1898.77 (19)
C7—C8—C9—C14177.05 (15)O2—C18—O1—C17170.55 (14)
C14—C9—C10—C112.0 (3)N1—C18—O1—C177.6 (2)
C8—C9—C10—C11175.63 (19)C8—C17—O1—C1810.0 (2)
C9—C10—C11—C121.1 (4)C16—C17—O1—C18168.77 (14)
 

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