2-Fluoro-N-[7-fluoro-3,4-di­hydro-2-methyl-3-oxo-4-(prop-2-ynyl)-2H-1,4-benzoxazin-6-yl]­benz­amide

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.

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

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Computing details

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

Crystal data

C19H14F2N2O3	Dx = 1.419 Mg m^−3
Mr = 356.32	Melting point: 229.42 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
a = 10.904 (4) Å	Cell parameters from 783 reflections
b = 8.670 (3) Å	θ = 3.1–21.8°
c = 35.271 (13) Å	µ = 0.11 mm^−1
V = 3334 (2) Å^3	T = 293 K
Z = 8	Block, colorless
F(000) = 1472	0.34 × 0.30 × 0.22 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	2942 independent reflections
Radiation source: fine-focus sealed tube	2003 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
φ and ω scans	θmax = 25.0°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −12→11
Tmin = 0.937, Tmax = 0.976	k = −10→10
14457 measured reflections	l = −41→19

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.054	w = 1/[σ^2(Fo^2) + (0.0402P)^2 + 2.5094P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.137	(Δ/σ)max = 0.001
S = 1.11	Δρmax = 0.27 e Å^−3
2942 reflections	Δρmin = −0.16 e Å^−3
236 parameters

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
F1	0.27155 (19)	1.1759 (2)	0.38709 (6)	0.0876 (7)
F2	0.2597 (2)	1.0144 (3)	0.47901 (6)	0.0946 (8)
O1	0.7390 (2)	0.9232 (3)	0.24376 (5)	0.0585 (6)
O2	0.50254 (18)	1.1674 (2)	0.27383 (5)	0.0498 (5)
O3	0.5263 (2)	0.7465 (3)	0.42645 (6)	0.0774 (8)
N1	0.6508 (2)	0.9402 (2)	0.30202 (6)	0.0389 (5)
N2	0.4048 (2)	0.9536 (3)	0.41919 (7)	0.0521 (7)
H2	0.3494	1.0075	0.4304	0.062*
C1	0.6549 (3)	0.9671 (3)	0.26369 (8)	0.0429 (7)
C2	0.5435 (3)	1.0495 (3)	0.24762 (8)	0.0512 (8)
H2A	0.4773	0.9742	0.2444	0.061*
C3	0.5674 (3)	1.1245 (4)	0.21061 (8)	0.0673 (10)
H3A	0.4925	1.1672	0.2009	0.101*
H3B	0.5985	1.0494	0.1931	0.101*
H3C	0.6266	1.2053	0.2139	0.101*
C4	0.4781 (3)	1.1098 (3)	0.30932 (8)	0.0425 (7)
C5	0.3835 (3)	1.1717 (4)	0.33014 (9)	0.0533 (8)
H5	0.3344	1.2499	0.3203	0.064*
C6	0.3639 (3)	1.1144 (4)	0.36583 (9)	0.0550 (8)
C7	0.4325 (3)	0.9977 (3)	0.38166 (8)	0.0463 (7)
C8	0.5279 (3)	0.9375 (3)	0.36030 (8)	0.0429 (7)
H8	0.5764	0.8590	0.3702	0.051*
C9	0.5512 (2)	0.9940 (3)	0.32421 (7)	0.0384 (6)
C10	0.7480 (3)	0.8473 (3)	0.31903 (7)	0.0411 (7)
H10A	0.8034	0.8129	0.2992	0.049*
H10B	0.7120	0.7565	0.3306	0.049*
C11	0.8181 (3)	0.9321 (3)	0.34776 (8)	0.0448 (7)
C12	0.8743 (3)	0.9998 (4)	0.37055 (9)	0.0649 (9)
H12	0.9189	1.0538	0.3887	0.078*
C13	0.4535 (3)	0.8385 (4)	0.43968 (8)	0.0493 (7)
C14	0.4181 (3)	0.8279 (3)	0.48066 (8)	0.0479 (7)
C15	0.3290 (3)	0.9120 (4)	0.49887 (9)	0.0587 (9)
C16	0.3037 (4)	0.8987 (5)	0.53685 (10)	0.0725 (10)
H16	0.2429	0.9586	0.5480	0.087*
C17	0.3696 (4)	0.7960 (5)	0.55788 (10)	0.0736 (11)
H17	0.3533	0.7849	0.5836	0.088*
C18	0.4597 (4)	0.7089 (4)	0.54125 (9)	0.0724 (10)
H18	0.5050	0.6392	0.5556	0.087*
C19	0.4827 (3)	0.7258 (4)	0.50300 (9)	0.0612 (9)
H19	0.5438	0.6662	0.4919	0.073*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0780 (14)	0.0988 (16)	0.0858 (14)	0.0448 (13)	0.0331 (12)	0.0099 (12)
F2	0.0882 (15)	0.1190 (18)	0.0768 (13)	0.0476 (14)	0.0331 (13)	0.0122 (13)
O1	0.0544 (13)	0.0735 (15)	0.0476 (11)	0.0186 (12)	0.0092 (11)	0.0023 (11)
O2	0.0521 (12)	0.0447 (11)	0.0527 (12)	0.0104 (10)	0.0020 (10)	0.0028 (10)
O3	0.1023 (19)	0.0780 (17)	0.0518 (13)	0.0395 (16)	0.0190 (13)	−0.0004 (12)
N1	0.0381 (13)	0.0393 (12)	0.0393 (12)	0.0079 (11)	0.0008 (10)	−0.0005 (10)
N2	0.0525 (16)	0.0525 (16)	0.0512 (15)	0.0117 (13)	0.0142 (12)	−0.0020 (13)
C1	0.0425 (17)	0.0411 (16)	0.0451 (17)	0.0006 (14)	−0.0010 (14)	−0.0031 (13)
C2	0.0525 (19)	0.0506 (17)	0.0505 (17)	0.0072 (16)	−0.0018 (15)	−0.0021 (15)
C3	0.079 (3)	0.069 (2)	0.0535 (19)	0.012 (2)	−0.0045 (18)	0.0036 (17)
C4	0.0401 (16)	0.0387 (15)	0.0488 (16)	−0.0008 (13)	0.0000 (14)	−0.0013 (13)
C5	0.0469 (18)	0.0502 (18)	0.063 (2)	0.0154 (15)	0.0029 (16)	0.0032 (16)
C6	0.0462 (18)	0.057 (2)	0.062 (2)	0.0152 (16)	0.0135 (16)	−0.0054 (16)
C7	0.0442 (17)	0.0475 (17)	0.0470 (16)	0.0034 (14)	0.0074 (14)	−0.0038 (14)
C8	0.0428 (17)	0.0401 (16)	0.0458 (16)	0.0048 (14)	0.0009 (13)	−0.0012 (13)
C9	0.0345 (15)	0.0358 (15)	0.0448 (16)	0.0003 (12)	0.0017 (13)	−0.0063 (12)
C10	0.0429 (16)	0.0357 (15)	0.0445 (15)	0.0075 (13)	0.0053 (14)	0.0036 (12)
C11	0.0481 (18)	0.0411 (16)	0.0452 (16)	0.0044 (14)	−0.0006 (15)	0.0094 (14)
C12	0.078 (3)	0.058 (2)	0.059 (2)	−0.0067 (19)	−0.017 (2)	0.0066 (17)
C13	0.0487 (18)	0.0513 (19)	0.0478 (17)	0.0016 (16)	0.0054 (15)	−0.0057 (15)
C14	0.0468 (18)	0.0487 (17)	0.0483 (17)	−0.0081 (15)	0.0072 (15)	−0.0057 (15)
C15	0.055 (2)	0.065 (2)	0.0562 (19)	0.0013 (18)	0.0127 (17)	−0.0008 (17)
C16	0.076 (3)	0.082 (3)	0.059 (2)	−0.001 (2)	0.0270 (19)	−0.009 (2)
C17	0.090 (3)	0.081 (3)	0.050 (2)	−0.016 (2)	0.014 (2)	−0.0046 (19)
C18	0.087 (3)	0.077 (3)	0.054 (2)	−0.002 (2)	0.001 (2)	0.0078 (19)
C19	0.065 (2)	0.061 (2)	0.0579 (19)	0.0035 (18)	0.0073 (18)	−0.0039 (17)

Geometric parameters (Å, º)

F1—C6	1.365 (3)	C5—H5	0.9300
F2—C15	1.360 (4)	C6—C7	1.376 (4)
O1—C1	1.216 (3)	C7—C8	1.386 (4)
O2—C4	1.374 (3)	C8—C9	1.387 (4)
O2—C2	1.449 (3)	C8—H8	0.9300
O3—C13	1.218 (3)	C10—C11	1.467 (4)
N1—C1	1.372 (3)	C10—H10A	0.9700
N1—C9	1.418 (3)	C10—H10B	0.9700
N1—C10	1.461 (3)	C11—C12	1.169 (4)
N2—C13	1.342 (4)	C12—H12	0.9300
N2—C7	1.411 (3)	C13—C14	1.498 (4)
N2—H2	0.8600	C14—C15	1.374 (4)
C1—C2	1.519 (4)	C14—C19	1.379 (4)
C2—C3	1.481 (4)	C15—C16	1.372 (4)
C2—H2A	0.9800	C16—C17	1.364 (5)
C3—H3A	0.9600	C16—H16	0.9300
C3—H3B	0.9600	C17—C18	1.371 (5)
C3—H3C	0.9600	C17—H17	0.9300
C4—C5	1.375 (4)	C18—C19	1.380 (5)
C4—C9	1.385 (4)	C18—H18	0.9300
C5—C6	1.370 (4)	C19—H19	0.9300
C4—O2—C2	112.6 (2)	C7—C8—H8	119.9
C1—N1—C9	120.9 (2)	C9—C8—H8	119.9
C1—N1—C10	118.3 (2)	C4—C9—C8	119.9 (3)
C9—N1—C10	120.7 (2)	C4—C9—N1	118.0 (2)
C13—N2—C7	128.5 (2)	C8—C9—N1	122.0 (2)
C13—N2—H2	115.8	N1—C10—C11	112.7 (2)
C7—N2—H2	115.8	N1—C10—H10A	109.1
O1—C1—N1	122.7 (3)	C11—C10—H10A	109.1
O1—C1—C2	122.3 (2)	N1—C10—H10B	109.1
N1—C1—C2	114.9 (2)	C11—C10—H10B	109.1
O2—C2—C3	107.9 (2)	H10A—C10—H10B	107.8
O2—C2—C1	109.9 (2)	C12—C11—C10	179.8 (4)
C3—C2—C1	113.2 (3)	C11—C12—H12	180.0
O2—C2—H2A	108.6	O3—C13—N2	122.6 (3)
C3—C2—H2A	108.6	O3—C13—C14	119.8 (3)
C1—C2—H2A	108.6	N2—C13—C14	117.6 (3)
C2—C3—H3A	109.5	C15—C14—C19	115.8 (3)
C2—C3—H3B	109.5	C15—C14—C13	126.9 (3)
H3A—C3—H3B	109.5	C19—C14—C13	117.3 (3)
C2—C3—H3C	109.5	F2—C15—C16	116.5 (3)
H3A—C3—H3C	109.5	F2—C15—C14	119.9 (3)
H3B—C3—H3C	109.5	C16—C15—C14	123.6 (3)
O2—C4—C5	119.3 (3)	C17—C16—C15	118.7 (3)
O2—C4—C9	119.8 (2)	C17—C16—H16	120.7
C5—C4—C9	120.8 (3)	C15—C16—H16	120.7
C6—C5—C4	117.7 (3)	C16—C17—C18	120.3 (3)
C6—C5—H5	121.1	C16—C17—H17	119.9
C4—C5—H5	121.1	C18—C17—H17	119.9
F1—C6—C5	118.5 (3)	C17—C18—C19	119.3 (4)
F1—C6—C7	117.8 (3)	C17—C18—H18	120.3
C5—C6—C7	123.7 (3)	C19—C18—H18	120.3
C6—C7—C8	117.6 (3)	C14—C19—C18	122.3 (3)
C6—C7—N2	117.6 (3)	C14—C19—H19	118.9
C8—C7—N2	124.7 (3)	C18—C19—H19	118.9
C7—C8—C9	120.2 (3)
C9—N1—C1—O1	179.8 (3)	C5—C4—C9—N1	−177.0 (2)
C10—N1—C1—O1	−3.6 (4)	C7—C8—C9—C4	−0.7 (4)
C9—N1—C1—C2	−3.0 (4)	C7—C8—C9—N1	177.4 (3)
C10—N1—C1—C2	173.6 (2)	C1—N1—C9—C4	−18.4 (4)
C4—O2—C2—C3	−179.8 (3)	C10—N1—C9—C4	165.1 (2)
C4—O2—C2—C1	−55.9 (3)	C1—N1—C9—C8	163.5 (3)
O1—C1—C2—O2	−143.6 (3)	C10—N1—C9—C8	−13.1 (4)
N1—C1—C2—O2	39.1 (3)	C1—N1—C10—C11	119.1 (3)
O1—C1—C2—C3	−22.9 (4)	C9—N1—C10—C11	−64.3 (3)
N1—C1—C2—C3	159.8 (3)	N1—C10—C11—C12	−87 (100)
C2—O2—C4—C5	−145.0 (3)	C7—N2—C13—O3	−5.3 (5)
C2—O2—C4—C9	37.2 (3)	C7—N2—C13—C14	172.9 (3)
O2—C4—C5—C6	−178.2 (3)	O3—C13—C14—C15	−173.0 (3)
C9—C4—C5—C6	−0.4 (4)	N2—C13—C14—C15	8.7 (5)
C4—C5—C6—F1	179.1 (3)	O3—C13—C14—C19	8.4 (4)
C4—C5—C6—C7	−0.8 (5)	N2—C13—C14—C19	−169.9 (3)
F1—C6—C7—C8	−178.7 (3)	C19—C14—C15—F2	−179.3 (3)
C5—C6—C7—C8	1.2 (5)	C13—C14—C15—F2	2.1 (5)
F1—C6—C7—N2	−1.9 (4)	C19—C14—C15—C16	0.3 (5)
C5—C6—C7—N2	177.9 (3)	C13—C14—C15—C16	−178.3 (3)
C13—N2—C7—C6	175.8 (3)	F2—C15—C16—C17	179.1 (3)
C13—N2—C7—C8	−7.6 (5)	C14—C15—C16—C17	−0.5 (6)
C6—C7—C8—C9	−0.4 (4)	C15—C16—C17—C18	0.5 (6)
N2—C7—C8—C9	−176.9 (3)	C16—C17—C18—C19	−0.3 (6)
O2—C4—C9—C8	178.9 (2)	C15—C14—C19—C18	−0.1 (5)
C5—C4—C9—C8	1.1 (4)	C13—C14—C19—C18	178.6 (3)
O2—C4—C9—N1	0.7 (4)	C17—C18—C19—C14	0.1 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O3^i	0.93	2.22	3.104 (4)	159

Symmetry code: (i) −x+3/2, y+1/2, z.