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The title compound, C19H14F2N2O3, known as a protox inhibitor, was synthesized from 7-fluoro-3,4-di­hydro-2-methyl­benzoxazinone. The bond lengths and angles are unexceptional and the heterocyclic ring adopts a screw-boat conformation. Molecules are linked into two-dimensional layers by intermolecular C—H...O hydrogen bonds, with an H...O distance of 2.22 Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804024304/wn6284sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804024304/wn6284Isup2.hkl
Contains datablock I

CCDC reference: 255876

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.054
  • wR factor = 0.137
  • Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 37 N1 -C10 -C11 -C12 -87.00100.00 1.555 1.555 1.555 1.555
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 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

2-Fluoro-N-[7-fluoro-3,4-dihydro-2-methyl-3-oxo-4-(prop-2-ynyl)- 2H-1,4-benzoxazin-6-yl]benzamide top
Crystal data top
C19H14F2N2O3Dx = 1.419 Mg m3
Mr = 356.32Melting point: 229.42 K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
a = 10.904 (4) ÅCell parameters from 783 reflections
b = 8.670 (3) Åθ = 3.1–21.8°
c = 35.271 (13) ŵ = 0.11 mm1
V = 3334 (2) Å3T = 293 K
Z = 8Block, colorless
F(000) = 14720.34 × 0.30 × 0.22 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
2942 independent reflections
Radiation source: fine-focus sealed tube2003 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
φ and ω scansθmax = 25.0°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 1211
Tmin = 0.937, Tmax = 0.976k = 1010
14457 measured reflectionsl = 4119
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.054 w = 1/[σ2(Fo2) + (0.0402P)2 + 2.5094P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.137(Δ/σ)max = 0.001
S = 1.11Δρmax = 0.27 e Å3
2942 reflectionsΔρmin = 0.16 e Å3
236 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.

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
xyzUiso*/Ueq
F10.27155 (19)1.1759 (2)0.38709 (6)0.0876 (7)
F20.2597 (2)1.0144 (3)0.47901 (6)0.0946 (8)
O10.7390 (2)0.9232 (3)0.24376 (5)0.0585 (6)
O20.50254 (18)1.1674 (2)0.27383 (5)0.0498 (5)
O30.5263 (2)0.7465 (3)0.42645 (6)0.0774 (8)
N10.6508 (2)0.9402 (2)0.30202 (6)0.0389 (5)
N20.4048 (2)0.9536 (3)0.41919 (7)0.0521 (7)
H20.34941.00750.43040.062*
C10.6549 (3)0.9671 (3)0.26369 (8)0.0429 (7)
C20.5435 (3)1.0495 (3)0.24762 (8)0.0512 (8)
H2A0.47730.97420.24440.061*
C30.5674 (3)1.1245 (4)0.21061 (8)0.0673 (10)
H3A0.49251.16720.20090.101*
H3B0.59851.04940.19310.101*
H3C0.62661.20530.21390.101*
C40.4781 (3)1.1098 (3)0.30932 (8)0.0425 (7)
C50.3835 (3)1.1717 (4)0.33014 (9)0.0533 (8)
H50.33441.24990.32030.064*
C60.3639 (3)1.1144 (4)0.36583 (9)0.0550 (8)
C70.4325 (3)0.9977 (3)0.38166 (8)0.0463 (7)
C80.5279 (3)0.9375 (3)0.36030 (8)0.0429 (7)
H80.57640.85900.37020.051*
C90.5512 (2)0.9940 (3)0.32421 (7)0.0384 (6)
C100.7480 (3)0.8473 (3)0.31903 (7)0.0411 (7)
H10A0.80340.81290.29920.049*
H10B0.71200.75650.33060.049*
C110.8181 (3)0.9321 (3)0.34776 (8)0.0448 (7)
C120.8743 (3)0.9998 (4)0.37055 (9)0.0649 (9)
H120.91891.05380.38870.078*
C130.4535 (3)0.8385 (4)0.43968 (8)0.0493 (7)
C140.4181 (3)0.8279 (3)0.48066 (8)0.0479 (7)
C150.3290 (3)0.9120 (4)0.49887 (9)0.0587 (9)
C160.3037 (4)0.8987 (5)0.53685 (10)0.0725 (10)
H160.24290.95860.54800.087*
C170.3696 (4)0.7960 (5)0.55788 (10)0.0736 (11)
H170.35330.78490.58360.088*
C180.4597 (4)0.7089 (4)0.54125 (9)0.0724 (10)
H180.50500.63920.55560.087*
C190.4827 (3)0.7258 (4)0.50300 (9)0.0612 (9)
H190.54380.66620.49190.073*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0780 (14)0.0988 (16)0.0858 (14)0.0448 (13)0.0331 (12)0.0099 (12)
F20.0882 (15)0.1190 (18)0.0768 (13)0.0476 (14)0.0331 (13)0.0122 (13)
O10.0544 (13)0.0735 (15)0.0476 (11)0.0186 (12)0.0092 (11)0.0023 (11)
O20.0521 (12)0.0447 (11)0.0527 (12)0.0104 (10)0.0020 (10)0.0028 (10)
O30.1023 (19)0.0780 (17)0.0518 (13)0.0395 (16)0.0190 (13)0.0004 (12)
N10.0381 (13)0.0393 (12)0.0393 (12)0.0079 (11)0.0008 (10)0.0005 (10)
N20.0525 (16)0.0525 (16)0.0512 (15)0.0117 (13)0.0142 (12)0.0020 (13)
C10.0425 (17)0.0411 (16)0.0451 (17)0.0006 (14)0.0010 (14)0.0031 (13)
C20.0525 (19)0.0506 (17)0.0505 (17)0.0072 (16)0.0018 (15)0.0021 (15)
C30.079 (3)0.069 (2)0.0535 (19)0.012 (2)0.0045 (18)0.0036 (17)
C40.0401 (16)0.0387 (15)0.0488 (16)0.0008 (13)0.0000 (14)0.0013 (13)
C50.0469 (18)0.0502 (18)0.063 (2)0.0154 (15)0.0029 (16)0.0032 (16)
C60.0462 (18)0.057 (2)0.062 (2)0.0152 (16)0.0135 (16)0.0054 (16)
C70.0442 (17)0.0475 (17)0.0470 (16)0.0034 (14)0.0074 (14)0.0038 (14)
C80.0428 (17)0.0401 (16)0.0458 (16)0.0048 (14)0.0009 (13)0.0012 (13)
C90.0345 (15)0.0358 (15)0.0448 (16)0.0003 (12)0.0017 (13)0.0063 (12)
C100.0429 (16)0.0357 (15)0.0445 (15)0.0075 (13)0.0053 (14)0.0036 (12)
C110.0481 (18)0.0411 (16)0.0452 (16)0.0044 (14)0.0006 (15)0.0094 (14)
C120.078 (3)0.058 (2)0.059 (2)0.0067 (19)0.017 (2)0.0066 (17)
C130.0487 (18)0.0513 (19)0.0478 (17)0.0016 (16)0.0054 (15)0.0057 (15)
C140.0468 (18)0.0487 (17)0.0483 (17)0.0081 (15)0.0072 (15)0.0057 (15)
C150.055 (2)0.065 (2)0.0562 (19)0.0013 (18)0.0127 (17)0.0008 (17)
C160.076 (3)0.082 (3)0.059 (2)0.001 (2)0.0270 (19)0.009 (2)
C170.090 (3)0.081 (3)0.050 (2)0.016 (2)0.014 (2)0.0046 (19)
C180.087 (3)0.077 (3)0.054 (2)0.002 (2)0.001 (2)0.0078 (19)
C190.065 (2)0.061 (2)0.0579 (19)0.0035 (18)0.0073 (18)0.0039 (17)
Geometric parameters (Å, º) top
F1—C61.365 (3)C5—H50.9300
F2—C151.360 (4)C6—C71.376 (4)
O1—C11.216 (3)C7—C81.386 (4)
O2—C41.374 (3)C8—C91.387 (4)
O2—C21.449 (3)C8—H80.9300
O3—C131.218 (3)C10—C111.467 (4)
N1—C11.372 (3)C10—H10A0.9700
N1—C91.418 (3)C10—H10B0.9700
N1—C101.461 (3)C11—C121.169 (4)
N2—C131.342 (4)C12—H120.9300
N2—C71.411 (3)C13—C141.498 (4)
N2—H20.8600C14—C151.374 (4)
C1—C21.519 (4)C14—C191.379 (4)
C2—C31.481 (4)C15—C161.372 (4)
C2—H2A0.9800C16—C171.364 (5)
C3—H3A0.9600C16—H160.9300
C3—H3B0.9600C17—C181.371 (5)
C3—H3C0.9600C17—H170.9300
C4—C51.375 (4)C18—C191.380 (5)
C4—C91.385 (4)C18—H180.9300
C5—C61.370 (4)C19—H190.9300
C4—O2—C2112.6 (2)C7—C8—H8119.9
C1—N1—C9120.9 (2)C9—C8—H8119.9
C1—N1—C10118.3 (2)C4—C9—C8119.9 (3)
C9—N1—C10120.7 (2)C4—C9—N1118.0 (2)
C13—N2—C7128.5 (2)C8—C9—N1122.0 (2)
C13—N2—H2115.8N1—C10—C11112.7 (2)
C7—N2—H2115.8N1—C10—H10A109.1
O1—C1—N1122.7 (3)C11—C10—H10A109.1
O1—C1—C2122.3 (2)N1—C10—H10B109.1
N1—C1—C2114.9 (2)C11—C10—H10B109.1
O2—C2—C3107.9 (2)H10A—C10—H10B107.8
O2—C2—C1109.9 (2)C12—C11—C10179.8 (4)
C3—C2—C1113.2 (3)C11—C12—H12180.0
O2—C2—H2A108.6O3—C13—N2122.6 (3)
C3—C2—H2A108.6O3—C13—C14119.8 (3)
C1—C2—H2A108.6N2—C13—C14117.6 (3)
C2—C3—H3A109.5C15—C14—C19115.8 (3)
C2—C3—H3B109.5C15—C14—C13126.9 (3)
H3A—C3—H3B109.5C19—C14—C13117.3 (3)
C2—C3—H3C109.5F2—C15—C16116.5 (3)
H3A—C3—H3C109.5F2—C15—C14119.9 (3)
H3B—C3—H3C109.5C16—C15—C14123.6 (3)
O2—C4—C5119.3 (3)C17—C16—C15118.7 (3)
O2—C4—C9119.8 (2)C17—C16—H16120.7
C5—C4—C9120.8 (3)C15—C16—H16120.7
C6—C5—C4117.7 (3)C16—C17—C18120.3 (3)
C6—C5—H5121.1C16—C17—H17119.9
C4—C5—H5121.1C18—C17—H17119.9
F1—C6—C5118.5 (3)C17—C18—C19119.3 (4)
F1—C6—C7117.8 (3)C17—C18—H18120.3
C5—C6—C7123.7 (3)C19—C18—H18120.3
C6—C7—C8117.6 (3)C14—C19—C18122.3 (3)
C6—C7—N2117.6 (3)C14—C19—H19118.9
C8—C7—N2124.7 (3)C18—C19—H19118.9
C7—C8—C9120.2 (3)
C9—N1—C1—O1179.8 (3)C5—C4—C9—N1177.0 (2)
C10—N1—C1—O13.6 (4)C7—C8—C9—C40.7 (4)
C9—N1—C1—C23.0 (4)C7—C8—C9—N1177.4 (3)
C10—N1—C1—C2173.6 (2)C1—N1—C9—C418.4 (4)
C4—O2—C2—C3179.8 (3)C10—N1—C9—C4165.1 (2)
C4—O2—C2—C155.9 (3)C1—N1—C9—C8163.5 (3)
O1—C1—C2—O2143.6 (3)C10—N1—C9—C813.1 (4)
N1—C1—C2—O239.1 (3)C1—N1—C10—C11119.1 (3)
O1—C1—C2—C322.9 (4)C9—N1—C10—C1164.3 (3)
N1—C1—C2—C3159.8 (3)N1—C10—C11—C1287 (100)
C2—O2—C4—C5145.0 (3)C7—N2—C13—O35.3 (5)
C2—O2—C4—C937.2 (3)C7—N2—C13—C14172.9 (3)
O2—C4—C5—C6178.2 (3)O3—C13—C14—C15173.0 (3)
C9—C4—C5—C60.4 (4)N2—C13—C14—C158.7 (5)
C4—C5—C6—F1179.1 (3)O3—C13—C14—C198.4 (4)
C4—C5—C6—C70.8 (5)N2—C13—C14—C19169.9 (3)
F1—C6—C7—C8178.7 (3)C19—C14—C15—F2179.3 (3)
C5—C6—C7—C81.2 (5)C13—C14—C15—F22.1 (5)
F1—C6—C7—N21.9 (4)C19—C14—C15—C160.3 (5)
C5—C6—C7—N2177.9 (3)C13—C14—C15—C16178.3 (3)
C13—N2—C7—C6175.8 (3)F2—C15—C16—C17179.1 (3)
C13—N2—C7—C87.6 (5)C14—C15—C16—C170.5 (6)
C6—C7—C8—C90.4 (4)C15—C16—C17—C180.5 (6)
N2—C7—C8—C9176.9 (3)C16—C17—C18—C190.3 (6)
O2—C4—C9—C8178.9 (2)C15—C14—C19—C180.1 (5)
C5—C4—C9—C81.1 (4)C13—C14—C19—C18178.6 (3)
O2—C4—C9—N10.7 (4)C17—C18—C19—C140.1 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···O3i0.932.223.104 (4)159
Symmetry code: (i) x+3/2, y+1/2, z.
 

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