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

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.

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

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

Crystal data

C19H14FIN2O4	Dx = 1.703 Mg m^−3
Mr = 480.22	Melting point: 281.88 K
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 908 reflections
a = 9.613 (4) Å	θ = 3.7–24.4°
b = 11.759 (5) Å	µ = 1.75 mm^−1
c = 16.571 (7) Å	T = 293 K
V = 1873.1 (14) Å^3	Plate, colourless
Z = 4	0.42 × 0.38 × 0.24 mm
F(000) = 944

Data collection

Bruker SMART CCD area-detector diffractometer	3752 independent reflections
Radiation source: fine-focus sealed tube	2828 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
φ and ω scans	θmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −11→12
Tmin = 0.472, Tmax = 0.658	k = −14→10
10073 measured reflections	l = −20→19

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0247P)^2] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.030	(Δ/σ)max = 0.001
wR(F^2) = 0.060	Δρmax = 0.36 e Å^−3
S = 0.99	Δρmin = −0.41 e Å^−3
3752 reflections	Absolute structure: Flack (1983), with XX Friedel pairs
244 parameters	Absolute structure parameter: 0.01 (2)
1 restraint

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
I1	0.11202 (3)	0.461567 (19)	0.66270 (3)	0.05838 (10)
F1	0.5273 (3)	1.0204 (2)	0.87142 (19)	0.0759 (8)
N1	0.2328 (3)	0.6344 (3)	0.95420 (17)	0.0407 (7)
N2	0.6202 (3)	0.8172 (3)	0.81260 (19)	0.0449 (8)
O1	0.0431 (3)	0.5620 (3)	1.01631 (17)	0.0600 (8)
O2	0.1642 (4)	0.8504 (3)	1.0145 (2)	0.0810 (11)
O3	0.5304 (3)	0.8860 (3)	0.69248 (17)	0.0698 (9)
O4	0.7781 (3)	0.7560 (2)	0.9078 (2)	0.0567 (9)
C1	0.1906 (5)	0.4870 (3)	0.7736 (3)	0.0515 (10)
C2	0.2283 (4)	0.5027 (3)	0.8405 (3)	0.0450 (10)
C3	0.2721 (5)	0.5215 (3)	0.9242 (3)	0.0479 (12)
H3A	0.2302	0.4639	0.9584	0.058*
H3B	0.3723	0.5131	0.9278	0.058*
C4	0.1153 (4)	0.6436 (4)	0.9989 (2)	0.0465 (10)
C5	0.0748 (4)	0.7621 (5)	1.0246 (3)	0.0710 (15)
H5A	−0.0102	0.7813	0.9962	0.085*
H5B	0.0518	0.7587	1.0816	0.085*
C6	0.2692 (4)	0.8379 (3)	0.9607 (2)	0.0436 (10)
C7	0.3093 (4)	0.7325 (3)	0.9313 (2)	0.0370 (9)
C8	0.4241 (4)	0.7271 (3)	0.8814 (2)	0.0438 (10)
H8	0.4514	0.6573	0.8603	0.053*
C9	0.4990 (4)	0.8236 (3)	0.8623 (2)	0.0428 (9)
C10	0.4539 (5)	0.9252 (3)	0.8913 (3)	0.0483 (10)
C11	0.3423 (5)	0.9350 (4)	0.9398 (3)	0.0562 (12)
H11	0.3147	1.0058	0.9591	0.067*
C12	0.6269 (5)	0.8510 (3)	0.7314 (3)	0.0529 (11)
C13	0.7737 (5)	0.8332 (4)	0.7068 (3)	0.0539 (13)
C14	0.8439 (4)	0.7924 (3)	0.7681 (3)	0.0489 (10)
C15	0.7508 (4)	0.7840 (3)	0.8398 (3)	0.0449 (9)
C16	0.9941 (4)	0.7567 (5)	0.7663 (3)	0.0688 (14)
H16A	1.0011	0.6745	0.7687	0.083*
H16B	1.0433	0.7884	0.8122	0.083*
C17	1.0576 (6)	0.8004 (6)	0.6877 (5)	0.103 (3)
H17A	1.0784	0.8807	0.6938	0.124*
H17B	1.1448	0.7610	0.6783	0.124*
C18	0.9662 (7)	0.7850 (6)	0.6158 (4)	0.100 (2)
H18A	0.9459	0.7048	0.6091	0.120*
H18B	1.0151	0.8108	0.5680	0.120*
C19	0.8291 (6)	0.8510 (5)	0.6239 (4)	0.0790 (19)
H19A	0.8452	0.9313	0.6145	0.095*
H19B	0.7626	0.8240	0.5843	0.095*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.08092 (18)	0.04596 (13)	0.04824 (13)	0.00249 (14)	−0.0111 (2)	−0.0073 (2)
F1	0.0762 (19)	0.0438 (16)	0.108 (2)	−0.0120 (14)	0.0230 (16)	0.0025 (15)
N1	0.0453 (19)	0.0402 (19)	0.0368 (15)	−0.0012 (16)	0.0007 (15)	−0.0023 (14)
N2	0.0387 (18)	0.050 (2)	0.0458 (18)	0.0026 (17)	0.0064 (16)	0.0052 (15)
O1	0.0618 (18)	0.070 (2)	0.0485 (17)	−0.0234 (17)	0.0090 (15)	0.0016 (14)
O2	0.081 (2)	0.055 (2)	0.107 (3)	0.0078 (19)	0.051 (2)	−0.0054 (18)
O3	0.079 (2)	0.072 (2)	0.058 (2)	0.0191 (19)	−0.0115 (16)	0.0043 (16)
O4	0.054 (2)	0.0592 (16)	0.0565 (17)	0.0039 (16)	−0.0092 (16)	−0.0003 (19)
C1	0.067 (3)	0.031 (2)	0.057 (3)	0.006 (2)	−0.007 (2)	−0.0070 (18)
C2	0.054 (3)	0.0287 (19)	0.052 (3)	0.0039 (18)	−0.004 (2)	−0.0034 (18)
C3	0.049 (3)	0.041 (2)	0.055 (3)	−0.004 (2)	0.000 (2)	0.006 (2)
C4	0.046 (2)	0.062 (3)	0.0314 (19)	−0.008 (2)	−0.004 (2)	−0.0025 (18)
C5	0.057 (3)	0.079 (4)	0.077 (3)	−0.020 (3)	0.024 (2)	−0.036 (3)
C6	0.042 (2)	0.047 (2)	0.042 (2)	0.006 (2)	0.0018 (19)	−0.0033 (19)
C7	0.036 (2)	0.038 (2)	0.037 (2)	−0.0013 (18)	−0.0043 (17)	−0.0033 (16)
C8	0.047 (2)	0.037 (2)	0.047 (2)	0.0029 (18)	0.0025 (19)	−0.0060 (18)
C9	0.041 (2)	0.046 (2)	0.042 (2)	0.002 (2)	−0.0016 (18)	−0.0024 (18)
C10	0.050 (2)	0.038 (2)	0.057 (2)	−0.005 (2)	0.000 (2)	−0.002 (2)
C11	0.058 (3)	0.039 (3)	0.072 (3)	0.008 (2)	0.013 (2)	−0.006 (2)
C12	0.066 (3)	0.037 (2)	0.055 (3)	0.000 (2)	0.005 (2)	−0.0021 (19)
C13	0.064 (3)	0.033 (3)	0.064 (3)	0.001 (2)	0.016 (3)	0.002 (2)
C14	0.045 (2)	0.035 (2)	0.067 (3)	−0.004 (2)	0.013 (2)	−0.010 (2)
C15	0.046 (2)	0.034 (2)	0.054 (3)	−0.005 (2)	0.005 (2)	−0.0061 (19)
C16	0.052 (3)	0.059 (3)	0.095 (4)	0.008 (3)	0.023 (3)	−0.016 (3)
C17	0.065 (3)	0.088 (4)	0.157 (8)	−0.004 (3)	0.052 (4)	−0.007 (4)
C18	0.116 (5)	0.086 (4)	0.098 (5)	0.005 (5)	0.063 (5)	0.010 (4)
C19	0.101 (4)	0.065 (4)	0.071 (3)	0.004 (3)	0.032 (3)	0.013 (3)

Geometric parameters (Å, º)

I1—C1	2.010 (5)	C7—C8	1.380 (5)
F1—C10	1.363 (5)	C8—C9	1.381 (5)
N1—C4	1.356 (5)	C8—H8	0.9300
N1—C7	1.419 (5)	C9—C10	1.358 (5)
N1—C3	1.467 (5)	C10—C11	1.346 (6)
N2—C15	1.391 (5)	C11—H11	0.9300
N2—C12	1.405 (5)	C12—C13	1.483 (6)
N2—C9	1.429 (5)	C13—C14	1.310 (7)
O1—C4	1.219 (5)	C13—C19	1.489 (6)
O2—C6	1.355 (5)	C14—C15	1.491 (6)
O2—C5	1.359 (5)	C14—C16	1.505 (6)
O3—C12	1.203 (5)	C16—C17	1.526 (8)
O4—C15	1.203 (5)	C16—H16A	0.9700
C1—C2	1.180 (5)	C16—H16B	0.9700
C2—C3	1.468 (6)	C17—C18	1.491 (9)
C3—H3A	0.9700	C17—H17A	0.9700
C3—H3B	0.9700	C17—H17B	0.9700
C4—C5	1.508 (6)	C18—C19	1.535 (8)
C5—H5A	0.9700	C18—H18A	0.9700
C5—H5B	0.9700	C18—H18B	0.9700
C6—C11	1.384 (6)	C19—H19A	0.9700
C6—C7	1.386 (5)	C19—H19B	0.9700
C4—N1—C7	120.8 (3)	C10—C11—C6	118.9 (4)
C4—N1—C3	118.2 (3)	C10—C11—H11	120.5
C7—N1—C3	120.8 (3)	C6—C11—H11	120.5
C15—N2—C12	110.4 (3)	O3—C12—N2	125.1 (4)
C15—N2—C9	124.3 (3)	O3—C12—C13	129.4 (4)
C12—N2—C9	125.1 (3)	N2—C12—C13	105.5 (4)
C6—O2—C5	118.0 (3)	C14—C13—C12	109.2 (4)
C2—C1—I1	175.8 (4)	C14—C13—C19	125.6 (5)
C1—C2—C3	178.8 (5)	C12—C13—C19	125.0 (5)
N1—C3—C2	112.5 (3)	C13—C14—C15	109.5 (4)
N1—C3—H3A	109.1	C13—C14—C16	125.5 (4)
C2—C3—H3A	109.1	C15—C14—C16	125.0 (4)
N1—C3—H3B	109.1	O4—C15—N2	125.3 (4)
C2—C3—H3B	109.1	O4—C15—C14	129.4 (4)
H3A—C3—H3B	107.8	N2—C15—C14	105.3 (4)
O1—C4—N1	122.7 (4)	C14—C16—C17	107.9 (5)
O1—C4—C5	121.0 (4)	C14—C16—H16A	110.1
N1—C4—C5	116.3 (4)	C17—C16—H16A	110.1
O2—C5—C4	120.6 (4)	C14—C16—H16B	110.1
O2—C5—H5A	107.2	C17—C16—H16B	110.1
C4—C5—H5A	107.2	H16A—C16—H16B	108.4
O2—C5—H5B	107.2	C18—C17—C16	113.9 (5)
C4—C5—H5B	107.2	C18—C17—H17A	108.8
H5A—C5—H5B	106.8	C16—C17—H17A	108.8
O2—C6—C11	116.9 (4)	C18—C17—H17B	108.8
O2—C6—C7	122.4 (4)	C16—C17—H17B	108.8
C11—C6—C7	120.6 (4)	H17A—C17—H17B	107.7
C8—C7—C6	118.3 (4)	C17—C18—C19	112.0 (6)
C8—C7—N1	122.5 (3)	C17—C18—H18A	109.2
C6—C7—N1	119.3 (3)	C19—C18—H18A	109.2
C7—C8—C9	121.1 (4)	C17—C18—H18B	109.2
C7—C8—H8	119.4	C19—C18—H18B	109.2
C9—C8—H8	119.4	H18A—C18—H18B	107.9
C10—C9—C8	118.4 (4)	C13—C19—C18	108.5 (5)
C10—C9—N2	120.7 (4)	C13—C19—H19A	110.0
C8—C9—N2	120.9 (3)	C18—C19—H19A	110.0
C11—C10—C9	122.7 (4)	C13—C19—H19B	110.0
C11—C10—F1	119.2 (4)	C18—C19—H19B	110.0
C9—C10—F1	118.1 (4)	H19A—C19—H19B	108.4
I1—C1—C2—C3	20 (24)	N2—C9—C10—F1	0.1 (6)
C4—N1—C3—C2	97.7 (4)	C9—C10—C11—C6	−0.7 (7)
C7—N1—C3—C2	−77.1 (5)	F1—C10—C11—C6	−179.1 (4)
C1—C2—C3—N1	−83 (21)	O2—C6—C11—C10	175.1 (4)
C7—N1—C4—O1	176.3 (3)	C7—C6—C11—C10	−0.7 (6)
C3—N1—C4—O1	1.5 (5)	C15—N2—C12—O3	−178.4 (4)
C7—N1—C4—C5	−2.0 (5)	C9—N2—C12—O3	−2.6 (7)
C3—N1—C4—C5	−176.8 (4)	C15—N2—C12—C13	1.8 (4)
C6—O2—C5—C4	19.5 (7)	C9—N2—C12—C13	177.6 (4)
O1—C4—C5—O2	171.2 (4)	O3—C12—C13—C14	−179.4 (4)
N1—C4—C5—O2	−10.5 (6)	N2—C12—C13—C14	0.4 (5)
C5—O2—C6—C11	167.9 (4)	O3—C12—C13—C19	−3.5 (9)
C5—O2—C6—C7	−16.3 (6)	N2—C12—C13—C19	176.2 (5)
O2—C6—C7—C8	−175.2 (4)	C12—C13—C14—C15	−2.3 (5)
C11—C6—C7—C8	0.5 (6)	C19—C13—C14—C15	−178.1 (5)
O2—C6—C7—N1	4.0 (6)	C12—C13—C14—C16	176.3 (4)
C11—C6—C7—N1	179.6 (4)	C19—C13—C14—C16	0.5 (8)
C4—N1—C7—C8	−175.6 (3)	C12—N2—C15—O4	176.3 (4)
C3—N1—C7—C8	−0.9 (5)	C9—N2—C15—O4	0.5 (6)
C4—N1—C7—C6	5.3 (5)	C12—N2—C15—C14	−3.1 (4)
C3—N1—C7—C6	180.0 (3)	C9—N2—C15—C14	−178.9 (3)
C6—C7—C8—C9	1.2 (5)	C13—C14—C15—O4	−176.0 (4)
N1—C7—C8—C9	−177.9 (3)	C16—C14—C15—O4	5.4 (7)
C7—C8—C9—C10	−2.6 (6)	C13—C14—C15—N2	3.3 (5)
C7—C8—C9—N2	178.1 (3)	C16—C14—C15—N2	−175.2 (4)
C15—N2—C9—C10	100.8 (5)	C13—C14—C16—C17	12.4 (7)
C12—N2—C9—C10	−74.4 (5)	C15—C14—C16—C17	−169.2 (4)
C15—N2—C9—C8	−79.9 (5)	C14—C16—C17—C18	−42.7 (7)
C12—N2—C9—C8	104.9 (5)	C16—C17—C18—C19	61.9 (7)
C8—C9—C10—C11	2.3 (7)	C14—C13—C19—C18	15.2 (9)
N2—C9—C10—C11	−178.4 (4)	C12—C13—C19—C18	−160.0 (5)
C8—C9—C10—F1	−179.2 (4)	C17—C18—C19—C13	−44.4 (7)