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The title compound, C16H16ClFN2O3, known as a protox inhibitor, was synthesized from 7-fluoro-2H-benz­[1,4]­oxazin-3(4H)-one. The bond lengths and angles are unexceptional and the heterocyclic ring adopts a screw-boat conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680402121X/wn6255sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680402121X/wn6255Isup2.hkl
Contains datablock I

CCDC reference: 253001

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.037
  • wR factor = 0.103
  • Data-to-parameter ratio = 13.4

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 ... # 20 N1 -C5 -C6 -C7 -6.00 13.00 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.

3-Chloro-N-(7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl)- 2,2-dimethylpropionamide top
Crystal data top
C16H16ClFN2O3F(000) = 704
Mr = 338.76Dx = 1.405 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.292 (4) ÅCell parameters from 903 reflections
b = 7.529 (2) Åθ = 2.6–25.9°
c = 17.213 (5) ŵ = 0.27 mm1
β = 111.607 (5)°T = 293 K
V = 1601.5 (8) Å3Block, colorless
Z = 40.26 × 0.24 × 0.20 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
2813 independent reflections
Radiation source: fine-focus sealed tube2157 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
φ and ω scansθmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 1515
Tmin = 0.930, Tmax = 0.948k = 88
6555 measured reflectionsl = 2019
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.037 w = 1/[σ2(Fo2) + (0.0478P)2 + 0.4903P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.103(Δ/σ)max = 0.001
S = 1.03Δρmax = 0.19 e Å3
2813 reflectionsΔρmin = 0.23 e Å3
210 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
Cl10.91868 (5)0.07858 (8)1.13147 (4)0.0663 (2)
F10.81674 (10)0.1382 (2)0.79840 (7)0.0682 (4)
O10.22392 (13)0.0684 (3)0.71987 (10)0.0779 (6)
O20.44259 (11)0.0558 (2)0.65097 (8)0.0512 (4)
O30.71855 (11)0.2528 (2)1.03954 (8)0.0520 (4)
N10.40373 (13)0.0734 (2)0.79758 (9)0.0418 (4)
N20.79358 (12)0.1861 (2)0.94458 (9)0.0412 (4)
H20.85460.17600.93830.049*
C10.31677 (17)0.0874 (3)0.72457 (13)0.0493 (5)
C20.34319 (17)0.1297 (3)0.64876 (12)0.0521 (6)
H2A0.28520.08590.59950.063*
H2B0.34620.25770.64350.063*
C30.52753 (16)0.0879 (3)0.72459 (11)0.0400 (5)
C40.51018 (15)0.1004 (2)0.79943 (11)0.0347 (4)
C50.38506 (17)0.0371 (3)0.87512 (12)0.0504 (6)
H5A0.31490.01890.86130.060*
H5B0.43960.04550.90900.060*
C60.38873 (17)0.1984 (4)0.92369 (13)0.0531 (6)
C70.3922 (2)0.3282 (4)0.96123 (16)0.0721 (8)
H70.39500.43200.99120.087*
C80.63041 (17)0.0995 (3)0.72369 (12)0.0474 (5)
H80.64250.08840.67400.057*
C90.71438 (16)0.1279 (3)0.79782 (12)0.0441 (5)
C100.70083 (15)0.1489 (3)0.87340 (11)0.0363 (4)
C110.59669 (15)0.1336 (3)0.87329 (11)0.0356 (4)
H110.58490.14570.92300.043*
C120.79899 (15)0.2359 (2)1.02187 (11)0.0352 (4)
C130.91208 (15)0.2731 (3)1.08707 (11)0.0376 (5)
C141.00477 (16)0.2526 (3)1.05529 (13)0.0537 (6)
H14A1.07170.28561.09870.081*
H14B0.99200.32821.00770.081*
H14C1.00880.13131.03960.081*
C150.9109 (2)0.4652 (3)1.11847 (14)0.0577 (6)
H15A0.85710.47521.14320.087*
H15B0.89420.54611.07230.087*
H15C0.98070.49361.15940.087*
C160.92862 (18)0.1504 (3)1.16103 (12)0.0479 (5)
H16A0.87460.17671.18490.058*
H16B0.99940.17241.20360.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0752 (4)0.0436 (4)0.0741 (4)0.0061 (3)0.0203 (3)0.0086 (3)
F10.0442 (7)0.1167 (12)0.0501 (7)0.0021 (7)0.0248 (6)0.0090 (7)
O10.0375 (9)0.1241 (17)0.0610 (10)0.0074 (9)0.0053 (8)0.0119 (10)
O20.0483 (9)0.0657 (10)0.0301 (7)0.0010 (7)0.0032 (6)0.0082 (7)
O30.0396 (8)0.0778 (11)0.0392 (7)0.0011 (7)0.0153 (6)0.0094 (7)
N10.0375 (9)0.0513 (11)0.0328 (8)0.0056 (8)0.0087 (7)0.0023 (7)
N20.0310 (8)0.0579 (11)0.0338 (8)0.0018 (8)0.0108 (7)0.0053 (8)
C10.0412 (13)0.0554 (14)0.0430 (12)0.0035 (10)0.0057 (10)0.0019 (10)
C20.0475 (13)0.0594 (15)0.0361 (11)0.0019 (11)0.0004 (9)0.0023 (10)
C30.0457 (12)0.0399 (11)0.0296 (10)0.0003 (9)0.0082 (8)0.0030 (8)
C40.0377 (11)0.0330 (10)0.0324 (10)0.0008 (8)0.0116 (8)0.0024 (8)
C50.0392 (12)0.0671 (16)0.0432 (12)0.0098 (10)0.0131 (9)0.0097 (11)
C60.0455 (12)0.0794 (18)0.0380 (11)0.0016 (12)0.0194 (10)0.0045 (12)
C70.0785 (18)0.095 (2)0.0531 (15)0.0034 (16)0.0360 (14)0.0070 (15)
C80.0519 (13)0.0618 (14)0.0316 (10)0.0021 (11)0.0191 (9)0.0049 (9)
C90.0352 (11)0.0587 (14)0.0405 (11)0.0020 (9)0.0165 (9)0.0028 (10)
C100.0367 (10)0.0403 (11)0.0306 (9)0.0011 (8)0.0107 (8)0.0009 (8)
C110.0372 (11)0.0406 (11)0.0284 (9)0.0002 (8)0.0114 (8)0.0002 (8)
C120.0388 (11)0.0335 (10)0.0335 (10)0.0006 (8)0.0135 (8)0.0018 (8)
C130.0393 (10)0.0385 (11)0.0324 (10)0.0049 (9)0.0100 (8)0.0038 (8)
C140.0395 (12)0.0697 (16)0.0501 (12)0.0134 (11)0.0144 (10)0.0111 (11)
C150.0665 (15)0.0481 (14)0.0555 (14)0.0117 (11)0.0190 (11)0.0137 (11)
C160.0480 (12)0.0515 (13)0.0358 (10)0.0010 (10)0.0054 (9)0.0012 (9)
Geometric parameters (Å, º) top
Cl1—C161.788 (2)C5—H5B0.9700
F1—C91.359 (2)C6—C71.163 (4)
O1—C11.215 (3)C7—H70.9300
O2—C31.373 (2)C8—C91.368 (3)
O2—C21.421 (3)C8—H80.9300
O3—C121.221 (2)C9—C101.387 (3)
N1—C11.363 (3)C10—C111.388 (3)
N1—C41.418 (2)C11—H110.9300
N1—C51.470 (2)C12—C131.535 (3)
N2—C121.358 (2)C13—C161.522 (3)
N2—C101.410 (2)C13—C141.529 (3)
N2—H20.8600C13—C151.546 (3)
C1—C21.505 (3)C14—H14A0.9600
C2—H2A0.9700C14—H14B0.9600
C2—H2B0.9700C14—H14C0.9600
C3—C81.376 (3)C15—H15A0.9600
C3—C41.393 (3)C15—H15B0.9600
C4—C111.387 (3)C15—H15C0.9600
C5—C61.465 (3)C16—H16A0.9700
C5—H5A0.9700C16—H16B0.9700
C3—O2—C2113.34 (15)C8—C9—C10123.35 (18)
C1—N1—C4120.68 (16)C9—C10—C11117.60 (16)
C1—N1—C5118.83 (17)C9—C10—N2117.65 (17)
C4—N1—C5120.45 (15)C11—C10—N2124.75 (16)
C12—N2—C10128.32 (16)C4—C11—C10120.37 (16)
C12—N2—H2115.8C4—C11—H11119.8
C10—N2—H2115.8C10—C11—H11119.8
O1—C1—N1123.2 (2)O3—C12—N2122.49 (17)
O1—C1—C2121.51 (19)O3—C12—C13120.70 (16)
N1—C1—C2115.24 (19)N2—C12—C13116.80 (16)
O2—C2—C1113.91 (17)C16—C13—C14110.55 (18)
O2—C2—H2A108.8C16—C13—C12107.57 (16)
C1—C2—H2A108.8C14—C13—C12114.93 (16)
O2—C2—H2B108.8C16—C13—C15106.99 (16)
C1—C2—H2B108.8C14—C13—C15109.42 (17)
H2A—C2—H2B107.7C12—C13—C15107.04 (16)
O2—C3—C8118.93 (17)C13—C14—H14A109.5
O2—C3—C4120.36 (18)C13—C14—H14B109.5
C8—C3—C4120.64 (17)H14A—C14—H14B109.5
C11—C4—C3119.75 (18)C13—C14—H14C109.5
C11—C4—N1121.99 (16)H14A—C14—H14C109.5
C3—C4—N1118.24 (16)H14B—C14—H14C109.5
C6—C5—N1112.50 (18)C13—C15—H15A109.5
C6—C5—H5A109.1C13—C15—H15B109.5
N1—C5—H5A109.1H15A—C15—H15B109.5
C6—C5—H5B109.1C13—C15—H15C109.5
N1—C5—H5B109.1H15A—C15—H15C109.5
H5A—C5—H5B107.8H15B—C15—H15C109.5
C7—C6—C5178.7 (2)C13—C16—Cl1111.98 (14)
C6—C7—H7180.0C13—C16—H16A109.2
C9—C8—C3118.19 (18)Cl1—C16—H16A109.2
C9—C8—H8120.9C13—C16—H16B109.2
C3—C8—H8120.9Cl1—C16—H16B109.2
F1—C9—C8119.11 (17)H16A—C16—H16B107.9
F1—C9—C10117.53 (17)
C4—N1—C1—O1178.8 (2)C3—C8—C9—C101.3 (3)
C5—N1—C1—O11.3 (3)F1—C9—C10—C11178.30 (18)
C4—N1—C1—C20.9 (3)C8—C9—C10—C112.4 (3)
C5—N1—C1—C2178.38 (19)F1—C9—C10—N22.3 (3)
C3—O2—C2—C149.2 (2)C8—C9—C10—N2176.9 (2)
O1—C1—C2—O2147.2 (2)C12—N2—C10—C9170.0 (2)
N1—C1—C2—O233.2 (3)C12—N2—C10—C119.3 (3)
C2—O2—C3—C8150.73 (19)C3—C4—C11—C102.0 (3)
C2—O2—C3—C432.1 (3)N1—C4—C11—C10176.17 (18)
O2—C3—C4—C11179.73 (18)C9—C10—C11—C40.7 (3)
C8—C3—C4—C113.2 (3)N2—C10—C11—C4178.60 (18)
O2—C3—C4—N12.0 (3)C10—N2—C12—O31.0 (3)
C8—C3—C4—N1175.07 (18)C10—N2—C12—C13178.22 (18)
C1—N1—C4—C11162.70 (19)O3—C12—C13—C1658.4 (2)
C5—N1—C4—C1114.8 (3)N2—C12—C13—C16122.33 (19)
C1—N1—C4—C319.1 (3)O3—C12—C13—C14177.99 (19)
C5—N1—C4—C3163.41 (18)N2—C12—C13—C141.3 (3)
C1—N1—C5—C698.3 (2)O3—C12—C13—C1556.3 (2)
C4—N1—C5—C679.2 (2)N2—C12—C13—C15122.99 (18)
N1—C5—C6—C76 (13)C14—C13—C16—Cl166.56 (19)
O2—C3—C8—C9178.67 (19)C12—C13—C16—Cl159.65 (19)
C4—C3—C8—C91.5 (3)C15—C13—C16—Cl1174.36 (15)
C3—C8—C9—F1179.41 (19)
 

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