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The title compound, C19H14FIN2O4, known as a protox inhibitor, was synthesized from flumioxazin. The cyclo­hexene ring in the mol­ecule is in a distorted chair conformation. The mol­ecules are connected into two-dimensional layers by C=O...I interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680401637X/ww6219sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680401637X/ww6219Isup2.hkl
Contains datablock I

CCDC reference: 248798

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.030
  • wR factor = 0.060
  • Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT431_ALERT_2_A Short Inter HL..A Contact I1 .. O1 .. 2.86 Ang.
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.78 Ratio PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... O2 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C17 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 1 I1 -C1 -C2 -C3 20.00 24.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 4 C1 -C2 -C3 -N1 -83.00 21.00 1.555 1.555 1.555 1.555
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.40 From the CIF: _reflns_number_total 3752 Count of symmetry unique reflns 1983 Completeness (_total/calc) 189.21% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1769 Fraction of Friedel pairs measured 0.892 Are heavy atom types Z>Si present yes
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 3 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-[7-Fluoro-3,4-dihydro-4-(3-iodoprop-2-ynyl)-3-oxo-2H-1,4-benzoxazin-6-yl]- 4,5,6,7-tetrahydro-2H-isoindole-1,3-dione top
Crystal data top
C19H14FIN2O4Dx = 1.703 Mg m3
Mr = 480.22Melting point: 281.88 K
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 908 reflections
a = 9.613 (4) Åθ = 3.7–24.4°
b = 11.759 (5) ŵ = 1.75 mm1
c = 16.571 (7) ÅT = 293 K
V = 1873.1 (14) Å3Plate, colourless
Z = 40.42 × 0.38 × 0.24 mm
F(000) = 944
Data collection top
Bruker SMART CCD area-detector
diffractometer
3752 independent reflections
Radiation source: fine-focus sealed tube2828 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
φ and ω scansθmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 1112
Tmin = 0.472, Tmax = 0.658k = 1410
10073 measured reflectionsl = 2019
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0247P)2]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.030(Δ/σ)max = 0.001
wR(F2) = 0.060Δρmax = 0.36 e Å3
S = 0.99Δρmin = 0.41 e Å3
3752 reflectionsAbsolute structure: Flack (1983), with XX Friedel pairs
244 parametersAbsolute structure parameter: 0.01 (2)
1 restraint
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
I10.11202 (3)0.461567 (19)0.66270 (3)0.05838 (10)
F10.5273 (3)1.0204 (2)0.87142 (19)0.0759 (8)
N10.2328 (3)0.6344 (3)0.95420 (17)0.0407 (7)
N20.6202 (3)0.8172 (3)0.81260 (19)0.0449 (8)
O10.0431 (3)0.5620 (3)1.01631 (17)0.0600 (8)
O20.1642 (4)0.8504 (3)1.0145 (2)0.0810 (11)
O30.5304 (3)0.8860 (3)0.69248 (17)0.0698 (9)
O40.7781 (3)0.7560 (2)0.9078 (2)0.0567 (9)
C10.1906 (5)0.4870 (3)0.7736 (3)0.0515 (10)
C20.2283 (4)0.5027 (3)0.8405 (3)0.0450 (10)
C30.2721 (5)0.5215 (3)0.9242 (3)0.0479 (12)
H3A0.23020.46390.95840.058*
H3B0.37230.51310.92780.058*
C40.1153 (4)0.6436 (4)0.9989 (2)0.0465 (10)
C50.0748 (4)0.7621 (5)1.0246 (3)0.0710 (15)
H5A0.01020.78130.99620.085*
H5B0.05180.75871.08160.085*
C60.2692 (4)0.8379 (3)0.9607 (2)0.0436 (10)
C70.3093 (4)0.7325 (3)0.9313 (2)0.0370 (9)
C80.4241 (4)0.7271 (3)0.8814 (2)0.0438 (10)
H80.45140.65730.86030.053*
C90.4990 (4)0.8236 (3)0.8623 (2)0.0428 (9)
C100.4539 (5)0.9252 (3)0.8913 (3)0.0483 (10)
C110.3423 (5)0.9350 (4)0.9398 (3)0.0562 (12)
H110.31471.00580.95910.067*
C120.6269 (5)0.8510 (3)0.7314 (3)0.0529 (11)
C130.7737 (5)0.8332 (4)0.7068 (3)0.0539 (13)
C140.8439 (4)0.7924 (3)0.7681 (3)0.0489 (10)
C150.7508 (4)0.7840 (3)0.8398 (3)0.0449 (9)
C160.9941 (4)0.7567 (5)0.7663 (3)0.0688 (14)
H16A1.00110.67450.76870.083*
H16B1.04330.78840.81220.083*
C171.0576 (6)0.8004 (6)0.6877 (5)0.103 (3)
H17A1.07840.88070.69380.124*
H17B1.14480.76100.67830.124*
C180.9662 (7)0.7850 (6)0.6158 (4)0.100 (2)
H18A0.94590.70480.60910.120*
H18B1.01510.81080.56800.120*
C190.8291 (6)0.8510 (5)0.6239 (4)0.0790 (19)
H19A0.84520.93130.61450.095*
H19B0.76260.82400.58430.095*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.08092 (18)0.04596 (13)0.04824 (13)0.00249 (14)0.0111 (2)0.0073 (2)
F10.0762 (19)0.0438 (16)0.108 (2)0.0120 (14)0.0230 (16)0.0025 (15)
N10.0453 (19)0.0402 (19)0.0368 (15)0.0012 (16)0.0007 (15)0.0023 (14)
N20.0387 (18)0.050 (2)0.0458 (18)0.0026 (17)0.0064 (16)0.0052 (15)
O10.0618 (18)0.070 (2)0.0485 (17)0.0234 (17)0.0090 (15)0.0016 (14)
O20.081 (2)0.055 (2)0.107 (3)0.0078 (19)0.051 (2)0.0054 (18)
O30.079 (2)0.072 (2)0.058 (2)0.0191 (19)0.0115 (16)0.0043 (16)
O40.054 (2)0.0592 (16)0.0565 (17)0.0039 (16)0.0092 (16)0.0003 (19)
C10.067 (3)0.031 (2)0.057 (3)0.006 (2)0.007 (2)0.0070 (18)
C20.054 (3)0.0287 (19)0.052 (3)0.0039 (18)0.004 (2)0.0034 (18)
C30.049 (3)0.041 (2)0.055 (3)0.004 (2)0.000 (2)0.006 (2)
C40.046 (2)0.062 (3)0.0314 (19)0.008 (2)0.004 (2)0.0025 (18)
C50.057 (3)0.079 (4)0.077 (3)0.020 (3)0.024 (2)0.036 (3)
C60.042 (2)0.047 (2)0.042 (2)0.006 (2)0.0018 (19)0.0033 (19)
C70.036 (2)0.038 (2)0.037 (2)0.0013 (18)0.0043 (17)0.0033 (16)
C80.047 (2)0.037 (2)0.047 (2)0.0029 (18)0.0025 (19)0.0060 (18)
C90.041 (2)0.046 (2)0.042 (2)0.002 (2)0.0016 (18)0.0024 (18)
C100.050 (2)0.038 (2)0.057 (2)0.005 (2)0.000 (2)0.002 (2)
C110.058 (3)0.039 (3)0.072 (3)0.008 (2)0.013 (2)0.006 (2)
C120.066 (3)0.037 (2)0.055 (3)0.000 (2)0.005 (2)0.0021 (19)
C130.064 (3)0.033 (3)0.064 (3)0.001 (2)0.016 (3)0.002 (2)
C140.045 (2)0.035 (2)0.067 (3)0.004 (2)0.013 (2)0.010 (2)
C150.046 (2)0.034 (2)0.054 (3)0.005 (2)0.005 (2)0.0061 (19)
C160.052 (3)0.059 (3)0.095 (4)0.008 (3)0.023 (3)0.016 (3)
C170.065 (3)0.088 (4)0.157 (8)0.004 (3)0.052 (4)0.007 (4)
C180.116 (5)0.086 (4)0.098 (5)0.005 (5)0.063 (5)0.010 (4)
C190.101 (4)0.065 (4)0.071 (3)0.004 (3)0.032 (3)0.013 (3)
Geometric parameters (Å, º) top
I1—C12.010 (5)C7—C81.380 (5)
F1—C101.363 (5)C8—C91.381 (5)
N1—C41.356 (5)C8—H80.9300
N1—C71.419 (5)C9—C101.358 (5)
N1—C31.467 (5)C10—C111.346 (6)
N2—C151.391 (5)C11—H110.9300
N2—C121.405 (5)C12—C131.483 (6)
N2—C91.429 (5)C13—C141.310 (7)
O1—C41.219 (5)C13—C191.489 (6)
O2—C61.355 (5)C14—C151.491 (6)
O2—C51.359 (5)C14—C161.505 (6)
O3—C121.203 (5)C16—C171.526 (8)
O4—C151.203 (5)C16—H16A0.9700
C1—C21.180 (5)C16—H16B0.9700
C2—C31.468 (6)C17—C181.491 (9)
C3—H3A0.9700C17—H17A0.9700
C3—H3B0.9700C17—H17B0.9700
C4—C51.508 (6)C18—C191.535 (8)
C5—H5A0.9700C18—H18A0.9700
C5—H5B0.9700C18—H18B0.9700
C6—C111.384 (6)C19—H19A0.9700
C6—C71.386 (5)C19—H19B0.9700
C4—N1—C7120.8 (3)C10—C11—C6118.9 (4)
C4—N1—C3118.2 (3)C10—C11—H11120.5
C7—N1—C3120.8 (3)C6—C11—H11120.5
C15—N2—C12110.4 (3)O3—C12—N2125.1 (4)
C15—N2—C9124.3 (3)O3—C12—C13129.4 (4)
C12—N2—C9125.1 (3)N2—C12—C13105.5 (4)
C6—O2—C5118.0 (3)C14—C13—C12109.2 (4)
C2—C1—I1175.8 (4)C14—C13—C19125.6 (5)
C1—C2—C3178.8 (5)C12—C13—C19125.0 (5)
N1—C3—C2112.5 (3)C13—C14—C15109.5 (4)
N1—C3—H3A109.1C13—C14—C16125.5 (4)
C2—C3—H3A109.1C15—C14—C16125.0 (4)
N1—C3—H3B109.1O4—C15—N2125.3 (4)
C2—C3—H3B109.1O4—C15—C14129.4 (4)
H3A—C3—H3B107.8N2—C15—C14105.3 (4)
O1—C4—N1122.7 (4)C14—C16—C17107.9 (5)
O1—C4—C5121.0 (4)C14—C16—H16A110.1
N1—C4—C5116.3 (4)C17—C16—H16A110.1
O2—C5—C4120.6 (4)C14—C16—H16B110.1
O2—C5—H5A107.2C17—C16—H16B110.1
C4—C5—H5A107.2H16A—C16—H16B108.4
O2—C5—H5B107.2C18—C17—C16113.9 (5)
C4—C5—H5B107.2C18—C17—H17A108.8
H5A—C5—H5B106.8C16—C17—H17A108.8
O2—C6—C11116.9 (4)C18—C17—H17B108.8
O2—C6—C7122.4 (4)C16—C17—H17B108.8
C11—C6—C7120.6 (4)H17A—C17—H17B107.7
C8—C7—C6118.3 (4)C17—C18—C19112.0 (6)
C8—C7—N1122.5 (3)C17—C18—H18A109.2
C6—C7—N1119.3 (3)C19—C18—H18A109.2
C7—C8—C9121.1 (4)C17—C18—H18B109.2
C7—C8—H8119.4C19—C18—H18B109.2
C9—C8—H8119.4H18A—C18—H18B107.9
C10—C9—C8118.4 (4)C13—C19—C18108.5 (5)
C10—C9—N2120.7 (4)C13—C19—H19A110.0
C8—C9—N2120.9 (3)C18—C19—H19A110.0
C11—C10—C9122.7 (4)C13—C19—H19B110.0
C11—C10—F1119.2 (4)C18—C19—H19B110.0
C9—C10—F1118.1 (4)H19A—C19—H19B108.4
I1—C1—C2—C320 (24)N2—C9—C10—F10.1 (6)
C4—N1—C3—C297.7 (4)C9—C10—C11—C60.7 (7)
C7—N1—C3—C277.1 (5)F1—C10—C11—C6179.1 (4)
C1—C2—C3—N183 (21)O2—C6—C11—C10175.1 (4)
C7—N1—C4—O1176.3 (3)C7—C6—C11—C100.7 (6)
C3—N1—C4—O11.5 (5)C15—N2—C12—O3178.4 (4)
C7—N1—C4—C52.0 (5)C9—N2—C12—O32.6 (7)
C3—N1—C4—C5176.8 (4)C15—N2—C12—C131.8 (4)
C6—O2—C5—C419.5 (7)C9—N2—C12—C13177.6 (4)
O1—C4—C5—O2171.2 (4)O3—C12—C13—C14179.4 (4)
N1—C4—C5—O210.5 (6)N2—C12—C13—C140.4 (5)
C5—O2—C6—C11167.9 (4)O3—C12—C13—C193.5 (9)
C5—O2—C6—C716.3 (6)N2—C12—C13—C19176.2 (5)
O2—C6—C7—C8175.2 (4)C12—C13—C14—C152.3 (5)
C11—C6—C7—C80.5 (6)C19—C13—C14—C15178.1 (5)
O2—C6—C7—N14.0 (6)C12—C13—C14—C16176.3 (4)
C11—C6—C7—N1179.6 (4)C19—C13—C14—C160.5 (8)
C4—N1—C7—C8175.6 (3)C12—N2—C15—O4176.3 (4)
C3—N1—C7—C80.9 (5)C9—N2—C15—O40.5 (6)
C4—N1—C7—C65.3 (5)C12—N2—C15—C143.1 (4)
C3—N1—C7—C6180.0 (3)C9—N2—C15—C14178.9 (3)
C6—C7—C8—C91.2 (5)C13—C14—C15—O4176.0 (4)
N1—C7—C8—C9177.9 (3)C16—C14—C15—O45.4 (7)
C7—C8—C9—C102.6 (6)C13—C14—C15—N23.3 (5)
C7—C8—C9—N2178.1 (3)C16—C14—C15—N2175.2 (4)
C15—N2—C9—C10100.8 (5)C13—C14—C16—C1712.4 (7)
C12—N2—C9—C1074.4 (5)C15—C14—C16—C17169.2 (4)
C15—N2—C9—C879.9 (5)C14—C16—C17—C1842.7 (7)
C12—N2—C9—C8104.9 (5)C16—C17—C18—C1961.9 (7)
C8—C9—C10—C112.3 (7)C14—C13—C19—C1815.2 (9)
N2—C9—C10—C11178.4 (4)C12—C13—C19—C18160.0 (5)
C8—C9—C10—F1179.2 (4)C17—C18—C19—C1344.4 (7)
 

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