2-{4-[(E)-2,3-Diiodo­allyl]-7-fluoro-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl}-2,3,4,5,6,7-hexa­hydro-1H-isoindole-1,3-dione

Pang, H.-L.; Huang, Y.; Yin, D.-L.; Yang, H.; Li, W.-A.

doi:10.1107/S1600536807020077

2-{4-[(E)-2,3-Diiodoallyl]-7-fluoro-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl}-2,3,4,5,6,7-hexahydro-1H-isoindole-1,3-dione

H.-L. Pang, Y. Huang, D.-L. Yin, H. Yang and W.-A. Li

In the title compound, C₁₉H₁₅FI₂N₂O₄, the cyclohexene and morpholinone rings adopt half-chair conformations. The dihedral angle between the benzene and pyrrole rings is 69.0 (2)°. The crystal packing is stabilized by C—H

O and C—H

F hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807020077/ci2366sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807020077/ci2366Isup2.hkl Contains datablock I

CCDC reference: 647716

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.006 Å
R factor = 0.030
wR factor = 0.079
Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT431_ALERT_2_B Short Inter HL..A Contact  I1     ..  O4      ..       3.06 Ang.

Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.64
PLAT432_ALERT_2_C Short Inter X...Y Contact  O2     ..  C4      ..       2.99 Ang.

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.643
            Tmax scaled      0.643 Tmin scaled      0.471

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   2 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
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Compounds containing 2H-benzo[b][1,4]oxazin-3(4H)-one groups are known to exhibit insecticidal (Nair et al., 2003) and herbicidal (Schallner et al., 2002) activities. As part of our investigations of the relationship between structure and bioactivity, we have synthesized a series of 2H-benzo[b][1,4]oxazin-3(4H)-one derivatives and we report here the structure of (I).

The cyclohexene ring adopts a half-chair conformation, with atoms C15 and C16 deviating from the C13/C14/C17/C18 plane by -0.192 (9) Å and 0.500 (9) Å, respectively. The morpholinone ring also adopts a half-chair conformation, with O2 and C5 deviating from the C4/C6/C11/N1 plane by -0.199 (6) and 0.344 (7) Å, respectively. The dihedral angle between the benzene and pyrrole rings is 69.0 (2)°.

The crystal packing is stabilized by intermolecular C—H···O and C—H···F hydrogen bonds (Table 1).

Related literature top

For general background, see: Nair et al. (2003); Schallner et al. (2002).

Experimental top

Iodine (1.91 g, 7.5 mmol) was dissolved in methanol (30 ml) and the solution was added slowly to a stirred solution of 2-(7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-\ 4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (1.8 g, 5 mmol) and potassium hydroxide (0.56 g, 10 mmol) in methanol (50 ml) at room temperature. The resulting mixture was stirred for 5 h, then poured into iced water (100 ml). After filtration, the solid was washed with water and recrystallized from acetonitrile. Yellow block-shaped single crystals of (I) were obtained by evaporation of the solvent over a period of two weeks.

Structure description top

The crystal packing is stabilized by intermolecular C—H···O and C—H···F hydrogen bonds (Table 1).

For general background, see: Nair et al. (2003); Schallner et al. (2002).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

Figures top

Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids. H atoms have been omitted for clarity.

2-{4-[(E)-2,3-Diiodoallyl]-7-fluoro-3-oxo-3,4-dihydro-2H- benzo[b][1,4]oxazin-6-yl}-2,3,4,5,6,7-hexahydro-1H-isoindole- 1,3-dione top

Crystal data top

C₁₉H₁₅FI₂N₂O₄	F(000) = 2320
M_r = 608.13	D_x = 2.004 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5415 reflections
a = 23.118 (4) Å	θ = 2.7–26.3°
b = 13.926 (2) Å	µ = 3.16 mm⁻¹
c = 14.975 (3) Å	T = 294 K
β = 123.266 (2)°	Block, yellow
V = 4030.9 (12) Å³	0.24 × 0.20 × 0.14 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	4138 independent reflections
Radiation source: fine-focus sealed tube	3361 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
φ and ω scans	θ_max = 26.4°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −28→28
T_min = 0.732, T_max = 1.000	k = −17→17
11268 measured reflections	l = −13→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.079	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0354P)² + 9.6041P] where P = (F_o² + 2F_c²)/3
4138 reflections	(Δ/σ)_max = 0.001
253 parameters	Δρ_max = 1.05 e Å⁻³
0 restraints	Δρ_min = −0.85 e Å⁻³

Crystal data top

C₁₉H₁₅FI₂N₂O₄	V = 4030.9 (12) Å³
M_r = 608.13	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 23.118 (4) Å	µ = 3.16 mm⁻¹
b = 13.926 (2) Å	T = 294 K
c = 14.975 (3) Å	0.24 × 0.20 × 0.14 mm
β = 123.266 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4138 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3361 reflections with I > 2σ(I)
T_min = 0.732, T_max = 1.000	R_int = 0.026
11268 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.079	H-atom parameters constrained
S = 1.01	Δρ_max = 1.05 e Å⁻³
4138 reflections	Δρ_min = −0.85 e Å⁻³
253 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

	x	y	z	U_iso*/U_eq
I1	0.085767 (14)	0.79872 (2)	0.22966 (2)	0.05341 (10)
I2	0.242669 (15)	0.56013 (2)	0.50881 (3)	0.05973 (11)
F1	0.09204 (15)	0.8397 (2)	0.7385 (2)	0.0669 (7)
O1	0.08081 (17)	0.4150 (2)	0.4174 (3)	0.0632 (8)
O2	0.06687 (15)	0.51904 (18)	0.6219 (2)	0.0504 (7)
O3	0.22865 (16)	0.9158 (2)	0.7464 (3)	0.0718 (10)
O4	0.02229 (15)	0.9427 (2)	0.4271 (2)	0.0582 (8)
N1	0.08795 (15)	0.5729 (2)	0.4618 (2)	0.0383 (7)
N2	0.11976 (15)	0.9039 (2)	0.5913 (2)	0.0383 (7)
C1	0.1654 (2)	0.7084 (3)	0.3419 (3)	0.0482 (9)
H1	0.2100	0.7189	0.3581	0.058*
C2	0.15559 (18)	0.6375 (3)	0.3907 (3)	0.0401 (8)
C3	0.08655 (19)	0.6034 (3)	0.3686 (3)	0.0404 (8)
H3A	0.0532	0.6551	0.3344	0.049*
H3B	0.0705	0.5503	0.3186	0.049*
C4	0.0862 (2)	0.4759 (3)	0.4793 (3)	0.0451 (9)
C5	0.0955 (2)	0.4511 (3)	0.5838 (4)	0.0531 (10)
H5A	0.0745	0.3890	0.5768	0.064*
H5B	0.1446	0.4449	0.6373	0.064*
C6	0.08179 (17)	0.6133 (3)	0.6143 (3)	0.0392 (8)
C7	0.0813 (2)	0.6781 (3)	0.6830 (3)	0.0469 (9)
H7	0.0733	0.6583	0.7347	0.056*
C8	0.0931 (2)	0.7739 (3)	0.6729 (3)	0.0456 (9)
C9	0.10596 (18)	0.8049 (2)	0.5982 (3)	0.0364 (7)
C10	0.10609 (17)	0.7381 (2)	0.5293 (3)	0.0351 (7)
H10	0.1151	0.7577	0.4788	0.042*
C11	0.09276 (17)	0.6418 (2)	0.5361 (3)	0.0346 (7)
C12	0.1811 (2)	0.9511 (3)	0.6655 (3)	0.0432 (9)
C13	0.17571 (19)	1.0491 (2)	0.6224 (3)	0.0391 (8)
C14	0.2311 (2)	1.1238 (3)	0.6715 (3)	0.0547 (11)
H14A	0.2717	1.1005	0.6745	0.066*
H14B	0.2442	1.1368	0.7439	0.066*
C15	0.2052 (3)	1.2164 (3)	0.6053 (4)	0.0656 (13)
H15A	0.1799	1.2538	0.6277	0.079*
H15B	0.2448	1.2542	0.6200	0.079*
C16	0.1595 (3)	1.1994 (3)	0.4877 (4)	0.0638 (12)
H16A	0.1853	1.1646	0.4643	0.077*
H16B	0.1459	1.2607	0.4509	0.077*
C17	0.0948 (2)	1.1424 (3)	0.4576 (4)	0.0539 (10)
H17A	0.0635	1.1822	0.4656	0.065*
H17B	0.0710	1.1218	0.3837	0.065*
C18	0.11612 (19)	1.0573 (2)	0.5290 (3)	0.0366 (8)
C19	0.07739 (19)	0.9643 (3)	0.5051 (3)	0.0374 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.05111 (17)	0.05720 (18)	0.05416 (17)	0.00914 (12)	0.03029 (14)	0.01610 (13)
I2	0.04430 (17)	0.0638 (2)	0.0657 (2)	0.02076 (13)	0.02673 (15)	0.01226 (14)
F1	0.100 (2)	0.0582 (15)	0.0623 (16)	−0.0063 (14)	0.0572 (16)	−0.0156 (12)
O1	0.074 (2)	0.0320 (14)	0.085 (2)	−0.0006 (14)	0.0442 (19)	−0.0107 (15)
O2	0.0565 (17)	0.0378 (14)	0.0631 (17)	−0.0050 (12)	0.0368 (15)	0.0070 (13)
O3	0.0561 (19)	0.0563 (18)	0.0576 (19)	−0.0079 (15)	0.0023 (16)	0.0142 (15)
O4	0.0465 (17)	0.0525 (17)	0.0503 (17)	−0.0066 (13)	0.0103 (14)	−0.0037 (13)
N1	0.0380 (16)	0.0302 (15)	0.0470 (17)	−0.0005 (12)	0.0235 (14)	−0.0023 (13)
N2	0.0420 (17)	0.0297 (14)	0.0382 (16)	−0.0025 (13)	0.0188 (14)	−0.0039 (12)
C1	0.039 (2)	0.058 (2)	0.051 (2)	0.0101 (18)	0.0262 (19)	0.0049 (19)
C2	0.0377 (19)	0.0395 (19)	0.041 (2)	0.0099 (15)	0.0207 (17)	−0.0019 (16)
C3	0.043 (2)	0.0351 (18)	0.0384 (19)	0.0034 (16)	0.0189 (17)	−0.0060 (15)
C4	0.039 (2)	0.0311 (18)	0.063 (2)	0.0017 (15)	0.0266 (19)	0.0030 (18)
C5	0.048 (2)	0.035 (2)	0.070 (3)	0.0056 (17)	0.029 (2)	0.0108 (19)
C6	0.0325 (18)	0.0366 (19)	0.044 (2)	−0.0026 (14)	0.0178 (16)	0.0066 (16)
C7	0.052 (2)	0.048 (2)	0.047 (2)	−0.0047 (18)	0.032 (2)	0.0025 (18)
C8	0.052 (2)	0.047 (2)	0.041 (2)	−0.0010 (18)	0.0277 (19)	−0.0043 (17)
C9	0.0359 (18)	0.0322 (17)	0.0383 (18)	−0.0012 (14)	0.0186 (16)	−0.0002 (15)
C10	0.0355 (19)	0.0335 (17)	0.0400 (19)	−0.0002 (14)	0.0230 (16)	−0.0011 (15)
C11	0.0270 (16)	0.0332 (17)	0.0387 (18)	0.0001 (13)	0.0150 (15)	−0.0006 (14)
C12	0.041 (2)	0.040 (2)	0.038 (2)	−0.0039 (16)	0.0150 (18)	−0.0032 (16)
C13	0.044 (2)	0.0317 (17)	0.0401 (19)	−0.0023 (15)	0.0224 (18)	−0.0057 (15)
C14	0.053 (2)	0.048 (2)	0.055 (2)	−0.0154 (19)	0.024 (2)	−0.0125 (19)
C15	0.074 (3)	0.044 (2)	0.080 (3)	−0.019 (2)	0.044 (3)	−0.009 (2)
C16	0.078 (3)	0.038 (2)	0.077 (3)	0.000 (2)	0.044 (3)	0.010 (2)
C17	0.057 (3)	0.045 (2)	0.054 (2)	0.0067 (19)	0.027 (2)	0.0070 (19)
C18	0.042 (2)	0.0313 (17)	0.0403 (19)	0.0014 (15)	0.0252 (17)	−0.0032 (15)
C19	0.037 (2)	0.0355 (18)	0.0386 (19)	0.0018 (15)	0.0197 (17)	−0.0067 (15)

Geometric parameters (Å, º) top

I1—C1	2.098 (4)	C6—C11	1.386 (5)
I2—C2	2.106 (3)	C7—C8	1.387 (6)
F1—C8	1.352 (4)	C7—H7	0.93
O1—C4	1.211 (5)	C8—C9	1.376 (5)
O2—C6	1.377 (4)	C9—C10	1.390 (5)
O2—C5	1.440 (5)	C10—C11	1.392 (5)
O3—C12	1.207 (5)	C10—H10	0.93
O4—C19	1.202 (4)	C12—C13	1.485 (5)
N1—C4	1.381 (5)	C13—C18	1.324 (5)
N1—C11	1.426 (5)	C13—C14	1.494 (5)
N1—C3	1.443 (5)	C14—C15	1.535 (6)
N2—C19	1.395 (5)	C14—H14A	0.97
N2—C12	1.397 (5)	C14—H14B	0.97
N2—C9	1.431 (4)	C15—C16	1.494 (7)
C1—C2	1.320 (6)	C15—H15A	0.97
C1—H1	0.93	C15—H15B	0.97
C2—C3	1.518 (5)	C16—C17	1.527 (6)
C3—H3A	0.97	C16—H16A	0.97
C3—H3B	0.97	C16—H16B	0.97
C4—C5	1.498 (6)	C17—C18	1.487 (5)
C5—H5A	0.97	C17—H17A	0.97
C5—H5B	0.97	C17—H17B	0.97
C6—C7	1.374 (5)	C18—C19	1.503 (5)

C6—O2—C5	113.8 (3)	C9—C10—H10	120.0
C4—N1—C11	120.5 (3)	C11—C10—H10	120.0
C4—N1—C3	118.9 (3)	C6—C11—C10	119.2 (3)
C11—N1—C3	120.5 (3)	C6—C11—N1	119.6 (3)
C19—N2—C12	110.1 (3)	C10—C11—N1	121.1 (3)
C19—N2—C9	125.2 (3)	O3—C12—N2	125.1 (3)
C12—N2—C9	124.4 (3)	O3—C12—C13	128.6 (4)
C2—C1—I1	123.3 (3)	N2—C12—C13	106.3 (3)
C2—C1—H1	118.3	C18—C13—C12	109.2 (3)
I1—C1—H1	118.3	C18—C13—C14	125.0 (3)
C1—C2—C3	126.4 (3)	C12—C13—C14	125.5 (3)
C1—C2—I2	118.2 (3)	C13—C14—C15	110.0 (4)
C3—C2—I2	115.4 (3)	C13—C14—H14A	109.7
N1—C3—C2	114.7 (3)	C15—C14—H14A	109.7
N1—C3—H3A	108.6	C13—C14—H14B	109.7
C2—C3—H3A	108.6	C15—C14—H14B	109.7
N1—C3—H3B	108.6	H14A—C14—H14B	108.2
C2—C3—H3B	108.6	C16—C15—C14	113.6 (4)
H3A—C3—H3B	107.6	C16—C15—H15A	108.8
O1—C4—N1	122.8 (4)	C14—C15—H15A	108.8
O1—C4—C5	122.3 (4)	C16—C15—H15B	108.8
N1—C4—C5	114.9 (3)	C14—C15—H15B	108.8
O2—C5—C4	115.4 (3)	H15A—C15—H15B	107.7
O2—C5—H5A	108.4	C15—C16—C17	112.1 (4)
C4—C5—H5A	108.4	C15—C16—H16A	109.2
O2—C5—H5B	108.4	C17—C16—H16A	109.2
C4—C5—H5B	108.4	C15—C16—H16B	109.2
H5A—C5—H5B	107.5	C17—C16—H16B	109.2
C7—C6—O2	117.3 (3)	H16A—C16—H16B	107.9
C7—C6—C11	121.7 (3)	C18—C17—C16	108.5 (3)
O2—C6—C11	120.9 (3)	C18—C17—H17A	110.0
C6—C7—C8	117.9 (4)	C16—C17—H17A	110.0
C6—C7—H7	121.1	C18—C17—H17B	110.0
C8—C7—H7	121.1	C16—C17—H17B	110.0
F1—C8—C9	118.4 (4)	H17A—C17—H17B	108.4
F1—C8—C7	119.3 (3)	C13—C18—C17	124.8 (3)
C9—C8—C7	122.3 (4)	C13—C18—C19	108.4 (3)
C8—C9—C10	118.9 (3)	C17—C18—C19	126.6 (3)
C8—C9—N2	121.2 (3)	O4—C19—N2	125.5 (3)
C10—C9—N2	120.0 (3)	O4—C19—C18	128.5 (4)
C9—C10—C11	120.0 (3)	N2—C19—C18	106.0 (3)

I1—C1—C2—C3	5.7 (6)	C9—C10—C11—C6	−2.2 (5)
I1—C1—C2—I2	−175.86 (18)	C9—C10—C11—N1	175.7 (3)
C4—N1—C3—C2	−104.5 (4)	C4—N1—C11—C6	−12.9 (5)
C11—N1—C3—C2	74.0 (4)	C3—N1—C11—C6	168.6 (3)
C1—C2—C3—N1	−143.5 (4)	C4—N1—C11—C10	169.2 (3)
I2—C2—C3—N1	38.0 (4)	C3—N1—C11—C10	−9.3 (5)
C11—N1—C4—O1	178.6 (3)	C19—N2—C12—O3	−177.3 (4)
C3—N1—C4—O1	−3.0 (6)	C9—N2—C12—O3	−3.1 (6)
C11—N1—C4—C5	−4.8 (5)	C19—N2—C12—C13	0.9 (4)
C3—N1—C4—C5	173.7 (3)	C9—N2—C12—C13	175.1 (3)
C6—O2—C5—C4	−45.6 (5)	O3—C12—C13—C18	177.0 (4)
O1—C4—C5—O2	−149.4 (4)	N2—C12—C13—C18	−1.1 (4)
N1—C4—C5—O2	33.9 (5)	O3—C12—C13—C14	2.0 (7)
C5—O2—C6—C7	−155.2 (4)	N2—C12—C13—C14	−176.1 (4)
C5—O2—C6—C11	28.5 (5)	C18—C13—C14—C15	7.4 (6)
O2—C6—C7—C8	−177.1 (3)	C12—C13—C14—C15	−178.3 (4)
C11—C6—C7—C8	−0.8 (6)	C13—C14—C15—C16	−36.9 (6)
C6—C7—C8—F1	179.2 (3)	C14—C15—C16—C17	60.0 (6)
C6—C7—C8—C9	−1.0 (6)	C15—C16—C17—C18	−48.6 (5)
F1—C8—C9—C10	−179.1 (3)	C12—C13—C18—C17	−174.8 (4)
C7—C8—C9—C10	1.1 (6)	C14—C13—C18—C17	0.3 (6)
F1—C8—C9—N2	1.6 (6)	C12—C13—C18—C19	0.8 (4)
C7—C8—C9—N2	−178.3 (4)	C14—C13—C18—C19	175.9 (4)
C19—N2—C9—C8	−114.3 (4)	C16—C17—C18—C13	20.0 (6)
C12—N2—C9—C8	72.4 (5)	C16—C17—C18—C19	−154.8 (4)
C19—N2—C9—C10	66.3 (5)	C12—N2—C19—O4	177.5 (4)
C12—N2—C9—C10	−107.0 (4)	C9—N2—C19—O4	3.3 (6)
C8—C9—C10—C11	0.5 (5)	C12—N2—C19—C18	−0.4 (4)
N2—C9—C10—C11	179.9 (3)	C9—N2—C19—C18	−174.6 (3)
C7—C6—C11—C10	2.3 (5)	C13—C18—C19—O4	−178.1 (4)
O2—C6—C11—C10	178.5 (3)	C17—C18—C19—O4	−2.6 (6)
C7—C6—C11—N1	−175.6 (3)	C13—C18—C19—N2	−0.3 (4)
O2—C6—C11—N1	0.6 (5)	C17—C18—C19—N2	175.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5B···O3ⁱ	0.97	2.49	3.449 (7)	171
C16—H16B···O1ⁱⁱ	0.97	2.51	3.366 (6)	147
C17—H17B···F1ⁱⁱⁱ	0.97	2.53	3.256 (6)	131

Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2; (ii) x, y+1, z; (iii) x, −y+2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₅FI₂N₂O₄
M_r	608.13
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	294
a, b, c (Å)	23.118 (4), 13.926 (2), 14.975 (3)
β (°)	123.266 (2)
V (Å³)	4030.9 (12)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	3.16
Crystal size (mm)	0.24 × 0.20 × 0.14

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.732, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	11268, 4138, 3361
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.079, 1.01
No. of reflections	4138
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.05, −0.85

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.