Crystal structure of 1,7,8,9-tetra­chloro-4-(2-fluoro­benz­yl)-10,10-dimeth­oxy-4-aza­tri­cyclo­[5.2.1.0^2,6]dec-8-ene-3,5-dione

In the title compound, C₁₇H₁₂Cl₄FNO₄, the configuration of the cyclo­alkene skeleton is endo,cis. The benzene ring is twisted by 71.01 (11)° from the attached pyrrolidine ring. In the crystal, one of the methine groups of the fused-ring system forms a weak C—H...O hydrogen bond. The other methine groups participates in a C—H...F inter­action to the same adjacent mol­ecule. Together, these generate [010] chains.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.046
• wR factor = 0.101
• Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N4     --  C5      ..        5.5 su
PLAT334_ALERT_2_C Small Average Benzene  C-C Dist. C11    -C16           1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0043 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.830 Check

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT434_ALERT_2_G Short Inter HL..HL Contact  Cl2    ..  Cl4     .       3.31 Ang.
PLAT791_ALERT_4_G The Model has Chirality at C1      .............          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C2      .............          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C6      .............          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C7      .............          R Verify
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT910_ALERT_3_G Missing # of FCF Reflections Below Th(Min) .....          4 Report

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

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

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S1. Comment

The title compound, (I)(Fig.1), 1,7,8,9-tetrachloro-4-(2'-fluorobenzyl) -10,10-dimethoxy-4-azatricyclo(5,2,1,0^2,6)dec-8-ene-3,5-dione was synthesized from N-(2'-fluorobenzyl)maleimide and 5,5-dimethoxy- 1,2,3,4-tetrachlorocydopentadiene.

The fused pyrrolidine ring systems, are frequently encountered structural units in many synthetically challenging and biologically active alkaloids. The interest of constructing skeletons of this type was further enlightened by the recent disclosure of Kossakowski et al., (2006) that the rigid arylcyclo analogues having azatricyclo ring systems show anti-HIV-1, anti-cancer, antiviral, and antibacterial activities. We have synthesized a serial compounds with this cycloalkene skeleton. This report is one of them.

In the crystal structure, there is a tricyclic fused pyrrolidine ring system. The configuration of the cycloalkene skeleton is endo, cis. The dihedral angle of pyrrolidine ring and benzene ring is 71.01 (11)°.

The molecules packed in spacegroup P2₁2₁2₁, and the absolute configuration of the title compound can be determined from Flack parameter x=-0.02 (7), and the compound has chirality at C1S, C2S, C6R, C7R.

Weak intermolecular C—H···X(X=O,F) hydrogen bonds can be found between adjacent molecules. In details(Table 1), C2—H2A and C6—H6A of the same molecule(1 - x, 1/2 + y, 1/2 - z) provide H-bonds donors to O2, F1, respectively. These pairs of H-bonds link the neighbour molecules along baxis to form infinite chains. Another two molecules in the unit cell along baxis linked by the same weak H-bonds in the opposite direction. So the whole crystal packing exists as countless helices along baxis.

Related literature

For similar structures, see: Shan et al. (2012); Kossakowski et al. (2009). For the biochemical activity of related compounds, see: Kossakowski et al. (2006, 2008); Struga et al. (2007).

S2. Experimental

The synthetic pathway for the title compound is described as follows. N-(2'fluorobenzyl)maleimide (1.9 g, 10 mmol) and 5,5- dimethoxy- 1,2,3,4-tetrachlorocydopentadiene (2.63 g, 10 mmol) were dissolved in anhydrous toluene (100 mL). Then the solution was refluxed for 8 h. After the solvent was removed under reduced pressure, the residue was dissolved in ether (150 mL), washed with water and brine, dried over anhydrous sodium sulfate, and concentrated to dryness. The product was purified by flash-chromatography (petroleum ether/ethyl acetate, 6:1) and the title compound was isolated as a white solid (3.86 g, 85%). m.p.: 116–118°C.

The crystals appropriate for X-ray data collection were obtained from ethyl acetate solution at room temperature after two days.

S3. Refinement

All H atoms were placed in geometically idealized positions and constrained to ride on their parent atoms with C—H distances of 0.93 Å (0.98 for alicylic CH) for aromatic ring CH, and U_iso(H) = 1.2(1.5 for CH₃)U_eq(C).

Computing details

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures

	Fig. 1. View of the molecule of (I) showing displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The C—H···X(X=O/F) interactions, dashed lines. Non-essential H atoms are omitted for clarity. Symmetry code: (i) 1 - x, 1/2 + y, 1/2 - z. (ii) 1 - x, y - 1/2, 1/2 - z.

1,7,8,9-Tetrachloro-4-(2-fluorobenzyl)-10,10-dimethoxy-4-azatricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione

Crystal data

C17H12Cl4FNO4	F(000) = 920
Mr = 455.08	Dx = 1.632 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4520 reflections
a = 9.965 (2) Å	θ = 3.0–27.5°
b = 10.982 (2) Å	µ = 0.67 mm^−1
c = 16.926 (3) Å	T = 296 K
V = 1852.1 (6) Å^3	Prismatic, colorless
Z = 4	0.20 × 0.15 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer	3231 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.069
Graphite monochromator	θmax = 27.5°, θmin = 3.0°
φ and ω scans	h = −12→12
17912 measured reflections	k = −14→14
4238 independent reflections	l = −21→21

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.101	w = 1/[σ^2(Fo^2) + (0.050P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
4238 reflections	Δρmax = 0.28 e Å^−3
244 parameters	Δρmin = −0.27 e Å^−3
0 restraints	Absolute structure: Flack (1983), 1826 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.02 (7)

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
Cl1	0.09057 (8)	0.72603 (7)	0.11428 (5)	0.0470 (2)
Cl2	0.31474 (10)	0.49911 (9)	0.37871 (5)	0.0614 (3)
Cl3	0.28576 (9)	0.30235 (7)	0.23337 (6)	0.0541 (2)
Cl4	0.16447 (10)	0.44681 (8)	0.07087 (5)	0.0549 (3)
F1	0.5234 (2)	0.33581 (19)	0.09916 (14)	0.0675 (6)
O1	0.4175 (2)	0.6801 (2)	0.03909 (14)	0.0582 (7)
O2	0.5994 (2)	0.4890 (2)	0.25327 (14)	0.0578 (6)
O3	0.1973 (2)	0.74679 (18)	0.30831 (13)	0.0420 (5)
O4	0.0408 (2)	0.59723 (19)	0.27636 (13)	0.0416 (5)
N4	0.5329 (2)	0.5781 (2)	0.13621 (15)	0.0354 (6)
C1	0.2012 (3)	0.6451 (2)	0.17531 (17)	0.0305 (6)
C2	0.3479 (3)	0.6939 (3)	0.17719 (17)	0.0328 (6)
H2A	0.3501	0.7825	0.1839	0.039*
C3	0.4315 (3)	0.6544 (3)	0.1073 (2)	0.0380 (7)
C5	0.5247 (3)	0.5554 (3)	0.21679 (19)	0.0394 (7)
C6	0.4076 (3)	0.6283 (3)	0.24928 (18)	0.0354 (7)
H6A	0.4383	0.6870	0.2889	0.042*
C7	0.2890 (3)	0.5511 (3)	0.28159 (17)	0.0365 (7)
C8	0.2570 (3)	0.4540 (3)	0.22159 (18)	0.0347 (7)
C9	0.2065 (3)	0.5094 (3)	0.15910 (17)	0.0335 (6)
C10	0.1705 (3)	0.6410 (3)	0.26658 (18)	0.0344 (7)
C11	0.6311 (3)	0.5241 (3)	0.08502 (18)	0.0357 (7)
C12	0.6251 (3)	0.4016 (3)	0.06730 (19)	0.0400 (7)
C13	0.7166 (4)	0.3465 (3)	0.0191 (2)	0.0529 (9)
H13A	0.7117	0.2634	0.0090	0.063*
C14	0.8162 (4)	0.4165 (3)	−0.0142 (2)	0.0517 (9)
H14A	0.8782	0.3810	−0.0481	0.062*
C15	0.8242 (3)	0.5388 (3)	0.0026 (2)	0.0511 (9)
H15A	0.8925	0.5855	−0.0195	0.061*
C16	0.7320 (3)	0.5925 (3)	0.0517 (2)	0.0458 (8)
H16A	0.7378	0.6753	0.0626	0.055*
C17	0.1104 (3)	0.8490 (3)	0.2942 (2)	0.0523 (9)
H17A	0.1389	0.9166	0.3260	0.078*
H17B	0.0199	0.8275	0.3078	0.078*
H17C	0.1144	0.8712	0.2394	0.078*
C18	−0.0074 (4)	0.5857 (4)	0.3562 (2)	0.0682 (12)
H18A	−0.0975	0.5547	0.3556	0.102*
H18B	−0.0063	0.6640	0.3814	0.102*
H18C	0.0493	0.5306	0.3848	0.102*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0449 (4)	0.0488 (4)	0.0472 (5)	0.0125 (4)	−0.0076 (4)	0.0056 (4)
Cl2	0.0770 (6)	0.0779 (6)	0.0295 (4)	0.0107 (5)	−0.0045 (4)	0.0089 (4)
Cl3	0.0587 (5)	0.0322 (4)	0.0714 (6)	0.0060 (4)	0.0034 (5)	0.0080 (4)
Cl4	0.0725 (6)	0.0539 (5)	0.0382 (5)	0.0019 (4)	−0.0065 (4)	−0.0174 (4)
F1	0.0668 (13)	0.0489 (11)	0.0869 (17)	−0.0211 (11)	0.0124 (13)	−0.0032 (11)
O1	0.0571 (15)	0.0707 (17)	0.0467 (15)	0.0238 (14)	0.0139 (13)	0.0245 (13)
O2	0.0512 (13)	0.0732 (16)	0.0489 (14)	0.0201 (14)	−0.0076 (12)	0.0059 (13)
O3	0.0397 (12)	0.0425 (12)	0.0438 (12)	0.0047 (10)	0.0007 (10)	−0.0187 (10)
O4	0.0354 (12)	0.0516 (13)	0.0380 (13)	−0.0048 (10)	0.0104 (9)	−0.0076 (10)
N4	0.0318 (13)	0.0332 (13)	0.0410 (16)	0.0069 (11)	0.0050 (11)	0.0015 (12)
C1	0.0289 (15)	0.0310 (14)	0.0315 (15)	0.0016 (12)	−0.0015 (13)	−0.0001 (12)
C2	0.0293 (14)	0.0277 (14)	0.0413 (17)	0.0005 (12)	0.0025 (13)	−0.0005 (13)
C3	0.0356 (16)	0.0309 (15)	0.048 (2)	0.0011 (13)	0.0073 (15)	0.0087 (14)
C5	0.0314 (16)	0.0379 (16)	0.049 (2)	0.0036 (14)	−0.0049 (15)	−0.0054 (15)
C6	0.0324 (15)	0.0363 (15)	0.0374 (17)	0.0006 (13)	−0.0038 (14)	−0.0072 (14)
C7	0.0409 (16)	0.0403 (15)	0.0282 (16)	0.0041 (14)	−0.0019 (14)	0.0023 (13)
C8	0.0369 (16)	0.0315 (14)	0.0356 (16)	0.0003 (13)	0.0015 (14)	0.0023 (13)
C9	0.0369 (15)	0.0328 (14)	0.0308 (15)	0.0001 (14)	0.0031 (12)	−0.0060 (13)
C10	0.0360 (16)	0.0357 (15)	0.0316 (16)	0.0008 (13)	−0.0004 (13)	−0.0054 (12)
C11	0.0343 (15)	0.0340 (15)	0.0389 (16)	0.0052 (13)	0.0005 (13)	0.0005 (13)
C12	0.0393 (18)	0.0385 (17)	0.0422 (19)	−0.0049 (14)	0.0008 (14)	0.0015 (14)
C13	0.062 (2)	0.0429 (18)	0.054 (2)	0.0043 (18)	−0.0030 (19)	−0.0170 (17)
C14	0.052 (2)	0.063 (2)	0.0401 (19)	0.0176 (18)	0.0028 (17)	−0.0024 (17)
C15	0.0406 (19)	0.055 (2)	0.057 (2)	0.0036 (17)	0.0133 (18)	0.0102 (18)
C16	0.0453 (19)	0.0336 (16)	0.058 (2)	−0.0006 (15)	0.0057 (17)	0.0055 (16)
C17	0.047 (2)	0.0437 (18)	0.066 (2)	0.0124 (16)	−0.0026 (18)	−0.0189 (17)
C18	0.064 (3)	0.086 (3)	0.054 (2)	−0.009 (2)	0.030 (2)	−0.004 (2)

Geometric parameters (Å, º)

Cl1—C1	1.753 (3)	C6—C7	1.554 (4)
Cl2—C7	1.759 (3)	C6—H6A	0.9800
Cl3—C8	1.702 (3)	C7—C8	1.506 (4)
Cl4—C9	1.696 (3)	C7—C10	1.560 (4)
F1—C12	1.356 (4)	C8—C9	1.320 (4)
O1—C3	1.197 (4)	C11—C16	1.376 (4)
O2—C5	1.211 (4)	C11—C12	1.380 (4)
O3—C10	1.385 (3)	C12—C13	1.365 (5)
O3—C17	1.438 (4)	C13—C14	1.376 (5)
O4—C10	1.389 (3)	C13—H13A	0.9300
O4—C18	1.440 (4)	C14—C15	1.375 (5)
N4—C5	1.389 (4)	C14—H14A	0.9300
N4—C3	1.401 (4)	C15—C16	1.372 (5)
N4—C11	1.435 (4)	C15—H15A	0.9300
C1—C9	1.516 (4)	C16—H16A	0.9300
C1—C2	1.557 (4)	C17—H17A	0.9600
C1—C10	1.576 (4)	C17—H17B	0.9600
C2—C3	1.511 (4)	C17—H17C	0.9600
C2—C6	1.537 (4)	C18—H18A	0.9600
C2—H2A	0.9800	C18—H18B	0.9600
C5—C6	1.518 (4)	C18—H18C	0.9600
C10—O3—C17	117.0 (2)	C8—C9—Cl4	127.8 (2)
C10—O4—C18	116.9 (3)	C1—C9—Cl4	123.3 (2)
C5—N4—C3	114.1 (3)	O3—C10—O4	114.1 (2)
C5—N4—C11	124.0 (2)	O3—C10—C7	107.6 (2)
C3—N4—C11	121.9 (3)	O4—C10—C7	117.7 (2)
C9—C1—C2	108.0 (2)	O3—C10—C1	116.0 (2)
C9—C1—C10	99.0 (2)	O4—C10—C1	107.9 (2)
C2—C1—C10	99.9 (2)	C7—C10—C1	91.8 (2)
C9—C1—Cl1	114.4 (2)	C16—C11—C12	118.4 (3)
C2—C1—Cl1	115.35 (19)	C16—C11—N4	121.3 (3)
C10—C1—Cl1	118.0 (2)	C12—C11—N4	120.3 (3)
C3—C2—C6	105.9 (2)	F1—C12—C13	120.0 (3)
C3—C2—C1	113.7 (2)	F1—C12—C11	117.7 (3)
C6—C2—C1	102.6 (2)	C13—C12—C11	122.2 (3)
C3—C2—H2A	111.4	C12—C13—C14	118.6 (3)
C6—C2—H2A	111.4	C12—C13—H13A	120.7
C1—C2—H2A	111.4	C14—C13—H13A	120.7
O1—C3—N4	124.2 (3)	C15—C14—C13	120.2 (3)
O1—C3—C2	128.5 (3)	C15—C14—H14A	119.9
N4—C3—C2	107.2 (3)	C13—C14—H14A	119.9
O2—C5—N4	124.9 (3)	C16—C15—C14	120.3 (3)
O2—C5—C6	127.2 (3)	C16—C15—H15A	119.8
N4—C5—C6	107.8 (2)	C14—C15—H15A	119.8
C5—C6—C2	104.9 (2)	C15—C16—C11	120.2 (3)
C5—C6—C7	115.1 (2)	C15—C16—H16A	119.9
C2—C6—C7	104.0 (2)	C11—C16—H16A	119.9
C5—C6—H6A	110.8	O3—C17—H17A	109.5
C2—C6—H6A	110.8	O3—C17—H17B	109.5
C7—C6—H6A	110.8	H17A—C17—H17B	109.5
C8—C7—C6	108.0 (2)	O3—C17—H17C	109.5
C8—C7—C10	100.3 (2)	H17A—C17—H17C	109.5
C6—C7—C10	99.9 (2)	H17B—C17—H17C	109.5
C8—C7—Cl2	115.6 (2)	O4—C18—H18A	109.5
C6—C7—Cl2	113.3 (2)	O4—C18—H18B	109.5
C10—C7—Cl2	117.9 (2)	H18A—C18—H18B	109.5
C9—C8—C7	107.1 (2)	O4—C18—H18C	109.5
C9—C8—Cl3	127.5 (2)	H18A—C18—H18C	109.5
C7—C8—Cl3	125.3 (2)	H18B—C18—H18C	109.5
C8—C9—C1	108.7 (3)
C9—C1—C2—C3	49.3 (3)	Cl1—C1—C9—C8	−160.5 (2)
C10—C1—C2—C3	152.2 (2)	C2—C1—C9—Cl4	−106.0 (3)
Cl1—C1—C2—C3	−80.2 (3)	C10—C1—C9—Cl4	150.4 (2)
C9—C1—C2—C6	−64.6 (3)	Cl1—C1—C9—Cl4	24.0 (3)
C10—C1—C2—C6	38.3 (2)	C17—O3—C10—O4	−55.9 (4)
Cl1—C1—C2—C6	165.98 (19)	C17—O3—C10—C7	171.5 (3)
C5—N4—C3—O1	−176.4 (3)	C17—O3—C10—C1	70.5 (3)
C11—N4—C3—O1	0.4 (5)	C18—O4—C10—O3	−49.8 (4)
C5—N4—C3—C2	3.3 (3)	C18—O4—C10—C7	77.8 (4)
C11—N4—C3—C2	−179.9 (3)	C18—O4—C10—C1	179.7 (3)
C6—C2—C3—O1	177.2 (3)	C8—C7—C10—O3	−170.1 (2)
C1—C2—C3—O1	65.3 (4)	C6—C7—C10—O3	−59.5 (3)
C6—C2—C3—N4	−2.4 (3)	Cl2—C7—C10—O3	63.6 (3)
C1—C2—C3—N4	−114.3 (3)	C8—C7—C10—O4	59.3 (3)
C3—N4—C5—O2	177.5 (3)	C6—C7—C10—O4	169.9 (2)
C11—N4—C5—O2	0.8 (5)	Cl2—C7—C10—O4	−67.0 (3)
C3—N4—C5—C6	−2.7 (3)	C8—C7—C10—C1	−52.0 (2)
C11—N4—C5—C6	−179.4 (3)	C6—C7—C10—C1	58.5 (2)
O2—C5—C6—C2	−179.2 (3)	Cl2—C7—C10—C1	−178.3 (2)
N4—C5—C6—C2	0.9 (3)	C9—C1—C10—O3	161.4 (2)
O2—C5—C6—C7	−65.6 (4)	C2—C1—C10—O3	51.1 (3)
N4—C5—C6—C7	114.5 (3)	Cl1—C1—C10—O3	−74.7 (3)
C3—C2—C6—C5	0.9 (3)	C9—C1—C10—O4	−69.1 (3)
C1—C2—C6—C5	120.4 (2)	C2—C1—C10—O4	−179.4 (2)
C3—C2—C6—C7	−120.4 (3)	Cl1—C1—C10—O4	54.8 (3)
C1—C2—C6—C7	−0.9 (3)	C9—C1—C10—C7	50.8 (2)
C5—C6—C7—C8	−47.1 (3)	C2—C1—C10—C7	−59.4 (2)
C2—C6—C7—C8	67.1 (3)	Cl1—C1—C10—C7	174.7 (2)
C5—C6—C7—C10	−151.4 (2)	C5—N4—C11—C16	−110.9 (4)
C2—C6—C7—C10	−37.3 (3)	C3—N4—C11—C16	72.6 (4)
C5—C6—C7—Cl2	82.2 (3)	C5—N4—C11—C12	69.9 (4)
C2—C6—C7—Cl2	−163.61 (19)	C3—N4—C11—C12	−106.6 (3)
C6—C7—C8—C9	−68.4 (3)	C16—C11—C12—F1	−178.6 (3)
C10—C7—C8—C9	35.7 (3)	N4—C11—C12—F1	0.6 (5)
Cl2—C7—C8—C9	163.6 (2)	C16—C11—C12—C13	1.0 (5)
C6—C7—C8—Cl3	110.2 (3)	N4—C11—C12—C13	−179.8 (3)
C10—C7—C8—Cl3	−145.7 (2)	F1—C12—C13—C14	178.1 (3)
Cl2—C7—C8—Cl3	−17.8 (3)	C11—C12—C13—C14	−1.5 (5)
C7—C8—C9—C1	−0.7 (3)	C12—C13—C14—C15	1.4 (6)
Cl3—C8—C9—C1	−179.2 (2)	C13—C14—C15—C16	−0.9 (6)
C7—C8—C9—Cl4	174.6 (2)	C14—C15—C16—C11	0.3 (5)
Cl3—C8—C9—Cl4	−4.0 (4)	C12—C11—C16—C15	−0.4 (5)
C2—C1—C9—C8	69.5 (3)	N4—C11—C16—C15	−179.6 (3)
C10—C1—C9—C8	−34.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O2^i	0.98	2.55	3.487 (4)	159
C6—H6A···F1^i	0.98	2.53	3.500 (4)	170

Symmetry code: (i) −x+1, y+1/2, −z+1/2.