Crystal structure of N,N′-bis­(2,4-di­fluoro­benzo­yloxy)benzene-1,2:4,5-tetra­carboximide

The title compound crystallizes with half a mol­ecule in the asymmetric unit and shows C_ar—H...F inter­actions in the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.048
• wR factor = 0.120
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.4 Note
PLAT334_ALERT_2_C Small Aver. Benzene C-C Dist C7       -C12A            1.37 Ang.
PLAT334_ALERT_2_C Small Aver. Benzene C-C Dist C7       -C12B            1.37 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9       ..F2               2.63 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.657 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          5 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          4 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          1 Report
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          2 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          1 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        16% Note
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O3             112.0 Degree
PLAT432_ALERT_2_G Short Inter X...Y Contact  O2       ..C5               2.92 Ang.
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          1 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          4 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         29 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          5 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  12 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012).

N,N'-Bis(2,4-difluorobenzoyloxy)benzene-1,2:4,5-tetracarboximide

Crystal data

C24H8F4N2O8	F(000) = 532
Mr = 528.32	Dx = 1.654 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.100 (6) Å	Cell parameters from 85 reflections
b = 4.744 (2) Å	θ = 5.1–21.4°
c = 13.662 (4) Å	µ = 0.15 mm^−1
β = 106.83 (2)°	T = 173 K
V = 1060.8 (7) Å^3	Plate, colourless
Z = 2	0.40 × 0.15 × 0.01 mm

Data collection

Bruker–Nonius KappaCCD diffractometer	2396 independent reflections
Radiation source: normal-focus sealed tube	1440 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
Detector resolution: 9 pixels mm^-1	θmax = 27.5°, θmin = 3.4°
CCD rotation images, thick slices scans	h = −22→21
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −6→6
Tmin = 0.931, Tmax = 0.986	l = −15→17
7948 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.045P)^2 + 0.4397P] where P = (Fo^2 + 2Fc^2)/3
2396 reflections	(Δ/σ)max < 0.001
176 parameters	Δρmax = 0.26 e Å^−3
1 restraint	Δρmin = −0.32 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The difluorophenyl ring is disordered over two orientations. The two split positions were refined by applying SADI restraints on bond lengths.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.53428 (13)	−0.2108 (5)	0.44840 (16)	0.0196 (5)
H1	0.557147	−0.349497	0.414668	0.024*
C2	0.47095 (12)	−0.0358 (5)	0.39704 (15)	0.0177 (5)
C3	0.43844 (12)	0.1672 (5)	0.44705 (16)	0.0191 (5)
C4	0.37402 (13)	0.3243 (5)	0.36996 (17)	0.0226 (5)
C5	0.42706 (13)	−0.0236 (5)	0.28530 (16)	0.0208 (5)
C6	0.24590 (14)	0.1960 (6)	0.15987 (18)	0.0306 (6)
C7	0.19802 (14)	0.3233 (6)	0.06271 (17)	0.0260 (5)
C9	0.07036 (16)	0.3516 (7)	−0.0723 (2)	0.0406 (7)
H9	0.015390	0.292807	−0.101232	0.049*
C10	0.10527 (16)	0.5453 (7)	−0.11934 (18)	0.0354 (7)
C11	0.18428 (15)	0.6341 (6)	−0.08085 (19)	0.0333 (6)
H11	0.206836	0.769181	−0.116313	0.040*
C8A	0.11781 (16)	0.2431 (6)	0.0194 (2)	0.0369 (7)	0.947 (4)
F1A	0.08458 (11)	0.0511 (5)	0.06620 (15)	0.0714 (8)	0.947 (4)
C12A	0.23029 (14)	0.5223 (6)	0.01072 (18)	0.0289 (6)	0.947 (4)
H12A	0.285205	0.582553	0.038893	0.035*	0.947 (4)
C8B	0.11781 (16)	0.2431 (6)	0.0194 (2)	0.0369 (7)	0.053 (4)
H8B	0.094436	0.108079	0.053933	0.044*	0.053 (4)
C12B	0.23029 (14)	0.5223 (6)	0.01072 (18)	0.0289 (6)	0.053 (4)
F1B	0.3060 (9)	0.615 (6)	0.037 (2)	0.043*	0.053 (4)
F2	0.05967 (10)	0.6562 (4)	−0.20823 (12)	0.0554 (6)
N1	0.37352 (12)	0.1997 (5)	0.27779 (14)	0.0256 (5)
O1	0.33327 (10)	0.5199 (4)	0.38057 (13)	0.0315 (4)
O2	0.43410 (10)	−0.1664 (4)	0.21582 (12)	0.0258 (4)
O3	0.32607 (9)	0.2995 (4)	0.18452 (11)	0.0268 (4)
O4	0.22619 (12)	0.0326 (6)	0.21309 (16)	0.0623 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0185 (10)	0.0213 (12)	0.0195 (10)	0.0013 (10)	0.0062 (8)	0.0007 (10)
C2	0.0187 (10)	0.0186 (12)	0.0162 (9)	−0.0022 (9)	0.0056 (8)	0.0006 (9)
C3	0.0162 (10)	0.0209 (12)	0.0195 (10)	−0.0013 (9)	0.0040 (8)	0.0037 (10)
C4	0.0197 (10)	0.0247 (13)	0.0220 (11)	0.0006 (10)	0.0038 (8)	0.0030 (11)
C5	0.0214 (10)	0.0206 (12)	0.0189 (10)	−0.0006 (10)	0.0037 (8)	0.0034 (10)
C6	0.0236 (12)	0.0388 (16)	0.0262 (12)	−0.0060 (12)	0.0023 (10)	0.0058 (12)
C7	0.0241 (11)	0.0309 (14)	0.0197 (11)	−0.0020 (11)	0.0012 (9)	0.0036 (11)
C9	0.0254 (12)	0.055 (2)	0.0326 (14)	−0.0102 (13)	−0.0051 (10)	0.0056 (14)
C10	0.0307 (13)	0.0479 (18)	0.0209 (11)	0.0052 (13)	−0.0034 (10)	0.0070 (13)
C11	0.0286 (12)	0.0401 (17)	0.0294 (13)	−0.0004 (12)	0.0055 (10)	0.0120 (12)
C8A	0.0308 (13)	0.0423 (17)	0.0331 (14)	−0.0113 (13)	0.0021 (11)	0.0098 (13)
F1A	0.0388 (10)	0.0959 (19)	0.0636 (13)	−0.0361 (11)	−0.0101 (9)	0.0451 (13)
C12A	0.0209 (11)	0.0368 (16)	0.0262 (11)	−0.0034 (11)	0.0021 (9)	0.0042 (12)
C8B	0.0308 (13)	0.0423 (17)	0.0331 (14)	−0.0113 (13)	0.0021 (11)	0.0098 (13)
C12B	0.0209 (11)	0.0368 (16)	0.0262 (11)	−0.0034 (11)	0.0021 (9)	0.0042 (12)
F2	0.0409 (9)	0.0744 (14)	0.0363 (9)	−0.0026 (9)	−0.0119 (7)	0.0227 (9)
N1	0.0271 (10)	0.0289 (12)	0.0162 (9)	0.0073 (9)	−0.0010 (7)	0.0046 (9)
O1	0.0284 (9)	0.0306 (10)	0.0324 (9)	0.0103 (8)	0.0037 (7)	0.0007 (8)
O2	0.0313 (9)	0.0267 (10)	0.0194 (8)	0.0009 (7)	0.0074 (7)	−0.0017 (8)
O3	0.0214 (8)	0.0352 (10)	0.0180 (7)	0.0013 (8)	−0.0035 (6)	0.0083 (8)
O4	0.0424 (12)	0.0860 (19)	0.0466 (12)	−0.0228 (12)	−0.0057 (9)	0.0414 (13)

Geometric parameters (Å, º)

C1—C2	1.384 (3)	C7—C12A	1.388 (4)
C1—C3^i	1.384 (3)	C9—C10	1.355 (4)
C1—H1	0.9500	C9—C8B	1.379 (4)
C2—C3	1.387 (3)	C9—C8A	1.379 (4)
C2—C5	1.494 (3)	C9—H9	0.9500
C3—C4	1.485 (3)	C10—F2	1.346 (3)
C4—O1	1.194 (3)	C10—C11	1.367 (4)
C4—N1	1.389 (3)	C11—C12B	1.377 (3)
C5—O2	1.200 (3)	C11—C12A	1.377 (3)
C5—N1	1.384 (3)	C11—H11	0.9500
C6—O4	1.177 (3)	C8A—F1A	1.331 (3)
C6—O3	1.402 (3)	C12A—H12A	0.9500
C6—C7	1.472 (3)	C8B—H8B	0.9500
C7—C8B	1.381 (3)	C12B—F1B	1.315 (10)
C7—C8A	1.381 (3)	N1—O3	1.381 (2)
C7—C12B	1.388 (4)
C2—C1—C3^i	114.5 (2)	C10—C9—H9	121.3
C2—C1—H1	122.8	C8A—C9—H9	121.3
C3^i—C1—H1	122.8	F2—C10—C9	118.3 (2)
C1—C2—C3	122.23 (19)	F2—C10—C11	118.5 (3)
C1—C2—C5	129.0 (2)	C9—C10—C11	123.3 (2)
C3—C2—C5	108.78 (19)	C10—C11—C12B	118.2 (2)
C1^i—C3—C2	123.3 (2)	C10—C11—C12A	118.2 (2)
C1^i—C3—C4	128.0 (2)	C10—C11—H11	120.9
C2—C3—C4	108.65 (19)	C12A—C11—H11	120.9
O1—C4—N1	126.2 (2)	F1A—C8A—C9	118.1 (2)
O1—C4—C3	130.0 (2)	F1A—C8A—C7	119.4 (2)
N1—C4—C3	103.76 (19)	C9—C8A—C7	122.5 (2)
O2—C5—N1	126.1 (2)	C11—C12A—C7	121.3 (2)
O2—C5—C2	130.6 (2)	C11—C12A—H12A	119.3
N1—C5—C2	103.36 (19)	C7—C12A—H12A	119.3
O4—C6—O3	121.1 (2)	C9—C8B—C7	122.5 (2)
O4—C6—C7	130.0 (2)	C9—C8B—H8B	118.8
O3—C6—C7	108.8 (2)	C7—C8B—H8B	118.8
C8B—C7—C12B	117.4 (2)	F1B—C12B—C11	112.2 (13)
C8A—C7—C12A	117.4 (2)	F1B—C12B—C7	126.4 (13)
C8B—C7—C6	119.9 (2)	C11—C12B—C7	121.3 (2)
C8A—C7—C6	119.9 (2)	O3—N1—C5	122.00 (19)
C12B—C7—C6	122.7 (2)	O3—N1—C4	122.6 (2)
C12A—C7—C6	122.7 (2)	C5—N1—C4	115.35 (19)
C10—C9—C8B	117.4 (2)	N1—O3—C6	111.96 (18)
C10—C9—C8A	117.4 (2)
C3^i—C1—C2—C3	0.5 (4)	C10—C9—C8A—F1A	−179.5 (3)
C3^i—C1—C2—C5	179.9 (2)	C10—C9—C8A—C7	−0.5 (5)
C1—C2—C3—C1^i	−0.5 (4)	C12A—C7—C8A—F1A	179.5 (3)
C5—C2—C3—C1^i	180.0 (2)	C6—C7—C8A—F1A	0.1 (4)
C1—C2—C3—C4	178.0 (2)	C12A—C7—C8A—C9	0.4 (4)
C5—C2—C3—C4	−1.6 (3)	C6—C7—C8A—C9	−179.0 (3)
C1^i—C3—C4—O1	1.0 (4)	C10—C11—C12A—C7	0.5 (4)
C2—C3—C4—O1	−177.4 (3)	C8A—C7—C12A—C11	−0.4 (4)
C1^i—C3—C4—N1	178.1 (2)	C6—C7—C12A—C11	179.0 (3)
C2—C3—C4—N1	−0.2 (2)	C10—C9—C8B—C7	−0.5 (5)
C1—C2—C5—O2	3.1 (4)	C12B—C7—C8B—C9	0.4 (4)
C3—C2—C5—O2	−177.4 (2)	C6—C7—C8B—C9	−179.0 (3)
C1—C2—C5—N1	−176.8 (2)	C10—C11—C12B—F1B	177.2 (15)
C3—C2—C5—N1	2.7 (2)	C10—C11—C12B—C7	0.5 (4)
O4—C6—C7—C8B	−2.9 (5)	C8B—C7—C12B—F1B	−176.7 (17)
O3—C6—C7—C8B	176.6 (3)	C6—C7—C12B—F1B	2.7 (18)
O4—C6—C7—C8A	−2.9 (5)	C8B—C7—C12B—C11	−0.4 (4)
O3—C6—C7—C8A	176.6 (3)	C6—C7—C12B—C11	179.0 (3)
O4—C6—C7—C12B	177.8 (3)	O2—C5—N1—O3	−6.0 (4)
O3—C6—C7—C12B	−2.7 (4)	C2—C5—N1—O3	173.86 (19)
O4—C6—C7—C12A	177.8 (3)	O2—C5—N1—C4	177.1 (2)
O3—C6—C7—C12A	−2.7 (4)	C2—C5—N1—C4	−3.0 (3)
C8B—C9—C10—F2	−179.2 (3)	O1—C4—N1—O3	2.6 (4)
C8A—C9—C10—F2	−179.2 (3)	C3—C4—N1—O3	−174.73 (19)
C8B—C9—C10—C11	0.6 (5)	O1—C4—N1—C5	179.4 (2)
C8A—C9—C10—C11	0.6 (5)	C3—C4—N1—C5	2.1 (3)
F2—C10—C11—C12B	179.2 (3)	C5—N1—O3—C6	99.6 (3)
C9—C10—C11—C12B	−0.5 (5)	C4—N1—O3—C6	−83.7 (3)
F2—C10—C11—C12A	179.2 (3)	O4—C6—O3—N1	−3.5 (4)
C9—C10—C11—C12A	−0.5 (5)	C7—C6—O3—N1	176.9 (2)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2^ii	0.95	2.37	3.271 (3)	158
C9—H9···F1A^iii	0.95	2.51	3.287 (3)	139
C9—H9···F2^iv	0.95	2.63	3.307 (3)	129
C11—H11···O1^v	0.95	2.39	3.200 (3)	143

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