4,5,6,7-Tetra­chloro-N-(2,3,4-trifluoro­phen­yl)phthalimide

Abstract

The asymmetric unit of the title compound, C₁₄H₂Cl₄F₃NO₂, contains two independent mol­ecules. In each mol­ecule, the phthalimide ring system is nearly planar [maximum atomic deviation = 0.031 (2) or 0.038 (2) Å] and oriented with respect to the benzene ring at 65.04 (7) or 71.76 (10)°. Weak inter­molecular C—H⋯O and C—H⋯F hydrogen bonding is present in the crystal structure.

Related literature

For the title compound as an inter­mediate of organic electro-luminescent materials, see: Han & Kay (2005 ▶). For the synthesis, see: Valkonen et al. (2007 ▶); Barchin et al. (2002 ▶). For related structures, see: Xu et al. (2006 ▶); Fu et al. (2010a ▶,b ▶,c ▶).

Experimental

Crystal data

• C₁₄H₂Cl₄F₃NO₂

• M _r = 414.97

• Triclinic,

• a = 6.7722 (7) Å

• b = 8.8052 (12) Å

• c = 24.493 (3) Å

• α = 95.777 (9)°

• β = 94.514 (17)°

• γ = 98.839 (12)°

• V = 1429.2 (3) ų

• Z = 4

• Mo Kα radiation

• μ = 0.87 mm⁻¹

• T = 113 K

• 0.20 × 0.18 × 0.12 mm

Data collection

• Rigaku Saturn 724CCD area-detector diffractometer

• Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.845, T _max = 0.903

• 13490 measured reflections

• 6684 independent reflections

• 4832 reflections with I > 2σ(I)

• R _int = 0.033

Refinement

• R[F ² > 2σ(F ²)] = 0.038

• wR(F ²) = 0.095

• S = 0.98

• 6684 reflections

• 433 parameters

• H-atom parameters constrained

• Δρ_max = 0.62 e Å⁻³

• Δρ_min = −0.38 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Supplementary material file. DOI: 10.1107/S1600536811020721/xu5228Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O3i	0.95	2.44	3.210 (3)	138
C27—H27⋯F3ii	0.95	2.45	3.379 (3)	165
C28—H28⋯O1	0.95	2.50	3.403 (3)	158

Symmetry codes: (i) ; (ii) .

supplementary crystallographic information

Comment

The title compound is a key intermediate of organic electro-luminescent, the emission of light by organic molecules exposed in the electric field, which has been wide investigated in academic and industrial displays (Han & Kay, 2005).

The molecular structure of the title compound is illustrated in Fig. 1. In the title compound, two rings are nearly planar, but the molecule as a whole is not planar. The dihedral angle between the benzene ring and the phthalimide plane is 66.03 (12) °, which is greater than 60.3 (5)° found in a related compound 2-(2-iodoethyl)isoindole-1,3-dione (Valkonen et al. 2007). Intermolecular weak C—H···O and C—H···F hydrogen bonding is present in the crystal structure (Table 1).

Experimental

Compound (I) was prepared according to the procedure in the literature (Barchin et al., 2002). The reaction was initiated by the addition of one molar equivalent of 2,3,4-trifluoroaniline and one molar equivalents of 4,5,6,7-tetrachlorophthalic anhydride and subsequent refluxing overnight, and then filtered. The crude produce was washed with water three times, and dried. The compound resulted (yield 96%) and single crystals suitable for X-ray analysis were obtained by slow evaporation of a ethyl acetate solution.

Refinement

H atoms were positioned geometrically and refined as riding with C—H = 0.95 Å, and U_iso(H) = 1.2U_eq(C).

Figures

Fig. 1.

View of the molecule of showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

C14H2Cl4F3NO2	Z = 4
Mr = 414.97	F(000) = 816
Triclinic, P1	Dx = 1.928 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.7722 (7) Å	Cell parameters from 4943 reflections
b = 8.8052 (12) Å	θ = 1.7–27.9°
c = 24.493 (3) Å	µ = 0.87 mm−1
α = 95.777 (9)°	T = 113 K
β = 94.514 (17)°	Prism, colorless
γ = 98.839 (12)°	0.20 × 0.18 × 0.12 mm
V = 1429.2 (3) Å3

Data collection

Rigaku Saturn 724CCD area-detector diffractometer	6684 independent reflections
Radiation source: rotating anode	4832 reflections with I > 2σ(I)
multilayer	Rint = 0.033
Detector resolution: 14.22 pixels mm-1	θmax = 27.9°, θmin = 1.7°
ω and φ scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −11→11
Tmin = 0.845, Tmax = 0.903	l = −31→32
13490 measured reflections

Refinement

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0384P)2] where P = (Fo2 + 2Fc2)/3
6684 reflections	(Δ/σ)max = 0.001
433 parameters	Δρmax = 0.62 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

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	0.32227 (8)	0.91214 (6)	0.18882 (2)	0.01916 (13)
Cl2	0.25294 (9)	0.79727 (7)	0.06239 (2)	0.02243 (14)
Cl3	0.24340 (8)	0.44993 (7)	0.02105 (2)	0.02233 (13)
Cl4	0.28079 (8)	0.20952 (6)	0.10536 (2)	0.01886 (13)
Cl5	0.83636 (8)	1.38342 (6)	0.20872 (2)	0.01938 (13)
Cl6	0.77697 (8)	1.27830 (6)	0.08171 (2)	0.02106 (13)
Cl7	0.75697 (8)	0.93290 (7)	0.03745 (2)	0.02244 (14)
Cl8	0.78622 (8)	0.68379 (6)	0.11969 (2)	0.01849 (13)
F1	0.09797 (18)	0.52932 (15)	0.35163 (5)	0.0272 (3)
F2	0.1377 (2)	0.44755 (17)	0.45515 (5)	0.0370 (4)
F3	0.4616 (2)	0.32808 (17)	0.48974 (5)	0.0351 (4)
F4	1.29401 (19)	1.04373 (16)	0.33909 (5)	0.0290 (3)
F5	1.4227 (2)	0.98029 (18)	0.44020 (6)	0.0427 (4)
F6	1.1612 (2)	0.82690 (18)	0.50178 (5)	0.0442 (4)
O1	0.3982 (2)	0.74947 (18)	0.29461 (6)	0.0233 (4)
O2	0.3402 (2)	0.23349 (17)	0.23416 (6)	0.0229 (4)
O3	0.9291 (2)	1.21384 (18)	0.31271 (6)	0.0216 (4)
O4	0.8648 (2)	0.70099 (18)	0.24803 (6)	0.0257 (4)
N1	0.3776 (3)	0.4840 (2)	0.27781 (7)	0.0171 (4)
N2	0.9077 (3)	0.9487 (2)	0.29353 (7)	0.0177 (4)
C1	0.3739 (3)	0.6333 (3)	0.26336 (9)	0.0176 (5)
C2	0.3363 (3)	0.6123 (2)	0.20166 (8)	0.0151 (5)
C3	0.3126 (3)	0.7200 (2)	0.16569 (9)	0.0163 (5)
C4	0.2817 (3)	0.6680 (3)	0.10912 (8)	0.0168 (5)
C5	0.2751 (3)	0.5115 (3)	0.09030 (8)	0.0166 (5)
C6	0.2956 (3)	0.4031 (2)	0.12762 (8)	0.0164 (5)
C7	0.3259 (3)	0.4568 (3)	0.18312 (8)	0.0160 (5)
C8	0.3474 (3)	0.3692 (3)	0.23222 (8)	0.0169 (5)
C9	0.4061 (3)	0.4492 (2)	0.33327 (8)	0.0180 (5)
C10	0.2611 (3)	0.4700 (3)	0.36825 (9)	0.0208 (5)
C11	0.2802 (3)	0.4284 (3)	0.42102 (9)	0.0241 (5)
C12	0.4469 (4)	0.3681 (3)	0.43799 (9)	0.0254 (6)
C13	0.5958 (4)	0.3496 (3)	0.40436 (9)	0.0251 (6)
H13	0.7109	0.3090	0.4171	0.030*
C14	0.5749 (3)	0.3914 (3)	0.35132 (9)	0.0211 (5)
H14	0.6769	0.3802	0.3274	0.025*
C15	0.8977 (3)	1.0995 (3)	0.28042 (8)	0.0165 (5)
C16	0.8468 (3)	1.0809 (2)	0.21917 (8)	0.0155 (5)
C17	0.8229 (3)	1.1919 (2)	0.18423 (8)	0.0167 (5)
C18	0.7927 (3)	1.1435 (3)	0.12721 (8)	0.0171 (5)
C19	0.7833 (3)	0.9880 (3)	0.10714 (8)	0.0170 (5)
C20	0.8001 (3)	0.8765 (2)	0.14369 (8)	0.0155 (5)
C21	0.8327 (3)	0.9259 (2)	0.19943 (8)	0.0155 (5)
C22	0.8675 (3)	0.8368 (3)	0.24746 (8)	0.0169 (5)
C23	0.9670 (3)	0.9153 (2)	0.34779 (8)	0.0189 (5)
C24	1.1641 (3)	0.9649 (3)	0.36851 (9)	0.0209 (5)
C25	1.2298 (4)	0.9340 (3)	0.42078 (9)	0.0257 (6)
C26	1.0962 (4)	0.8546 (3)	0.45089 (9)	0.0294 (6)
C27	0.8992 (4)	0.8043 (3)	0.43104 (9)	0.0316 (6)
H27	0.8088	0.7490	0.4526	0.038*
C28	0.8346 (4)	0.8359 (3)	0.37858 (9)	0.0254 (5)
H28	0.6988	0.8026	0.3641	0.031*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
Cl1	0.0216 (3)	0.0129 (3)	0.0235 (3)	0.0040 (2)	0.0019 (2)	0.0027 (2)
Cl2	0.0282 (3)	0.0206 (3)	0.0198 (3)	0.0039 (3)	0.0020 (2)	0.0088 (2)
Cl3	0.0299 (3)	0.0228 (3)	0.0139 (2)	0.0036 (3)	0.0013 (2)	0.0017 (2)
Cl4	0.0233 (3)	0.0144 (3)	0.0185 (3)	0.0032 (2)	0.0022 (2)	−0.0004 (2)
Cl5	0.0240 (3)	0.0126 (3)	0.0220 (3)	0.0042 (2)	0.0030 (2)	0.0020 (2)
Cl6	0.0251 (3)	0.0195 (3)	0.0201 (3)	0.0044 (2)	0.0025 (2)	0.0083 (2)
Cl7	0.0308 (3)	0.0228 (3)	0.0136 (3)	0.0044 (3)	0.0018 (2)	0.0017 (2)
Cl8	0.0228 (3)	0.0142 (3)	0.0179 (3)	0.0029 (2)	0.0021 (2)	−0.0008 (2)
F1	0.0239 (7)	0.0282 (8)	0.0303 (7)	0.0102 (6)	0.0008 (6)	0.0002 (6)
F2	0.0414 (9)	0.0446 (10)	0.0289 (8)	0.0109 (8)	0.0184 (7)	0.0044 (7)
F3	0.0549 (10)	0.0372 (10)	0.0147 (7)	0.0081 (8)	0.0041 (7)	0.0084 (6)
F4	0.0300 (8)	0.0265 (8)	0.0295 (8)	−0.0009 (6)	0.0030 (6)	0.0068 (6)
F5	0.0369 (9)	0.0459 (11)	0.0404 (9)	−0.0005 (8)	−0.0177 (7)	0.0088 (8)
F6	0.0619 (11)	0.0490 (11)	0.0223 (8)	0.0097 (9)	−0.0087 (7)	0.0154 (7)
O1	0.0322 (10)	0.0181 (9)	0.0186 (8)	0.0070 (8)	−0.0033 (7)	−0.0026 (7)
O2	0.0354 (10)	0.0141 (9)	0.0192 (8)	0.0041 (7)	0.0022 (7)	0.0026 (6)
O3	0.0298 (9)	0.0161 (9)	0.0179 (8)	0.0053 (7)	0.0002 (7)	−0.0031 (6)
O4	0.0417 (11)	0.0150 (9)	0.0202 (8)	0.0056 (8)	0.0000 (8)	0.0019 (7)
N1	0.0248 (10)	0.0137 (10)	0.0130 (9)	0.0047 (8)	0.0000 (8)	0.0013 (7)
N2	0.0267 (11)	0.0128 (10)	0.0137 (9)	0.0038 (8)	0.0002 (8)	0.0019 (7)
C1	0.0191 (12)	0.0163 (12)	0.0173 (11)	0.0046 (10)	−0.0019 (9)	0.0014 (9)
C2	0.0131 (11)	0.0154 (12)	0.0162 (10)	0.0013 (9)	0.0005 (9)	0.0019 (8)
C3	0.0146 (11)	0.0124 (11)	0.0215 (11)	0.0018 (9)	0.0020 (9)	0.0009 (9)
C4	0.0155 (11)	0.0168 (12)	0.0183 (11)	0.0015 (9)	0.0009 (9)	0.0062 (9)
C5	0.0160 (11)	0.0182 (12)	0.0153 (10)	0.0006 (9)	0.0029 (9)	0.0022 (9)
C6	0.0148 (11)	0.0150 (12)	0.0190 (11)	0.0017 (9)	0.0021 (9)	0.0011 (9)
C7	0.0152 (11)	0.0147 (11)	0.0184 (11)	0.0035 (9)	0.0015 (9)	0.0019 (9)
C8	0.0188 (12)	0.0164 (12)	0.0158 (11)	0.0053 (10)	0.0017 (9)	0.0003 (9)
C9	0.0272 (13)	0.0139 (11)	0.0122 (10)	0.0025 (10)	−0.0002 (9)	0.0008 (8)
C10	0.0229 (13)	0.0174 (12)	0.0215 (11)	0.0047 (10)	−0.0008 (10)	−0.0017 (9)
C11	0.0295 (14)	0.0235 (14)	0.0187 (11)	0.0014 (11)	0.0096 (10)	−0.0013 (10)
C12	0.0417 (16)	0.0206 (13)	0.0130 (11)	0.0006 (11)	0.0019 (11)	0.0039 (9)
C13	0.0313 (14)	0.0260 (14)	0.0192 (12)	0.0095 (11)	−0.0024 (10)	0.0043 (10)
C14	0.0255 (13)	0.0202 (13)	0.0188 (11)	0.0057 (10)	0.0048 (10)	0.0022 (9)
C15	0.0168 (11)	0.0150 (12)	0.0182 (11)	0.0039 (9)	0.0013 (9)	0.0024 (9)
C16	0.0144 (11)	0.0167 (12)	0.0149 (10)	0.0025 (9)	0.0007 (9)	0.0005 (9)
C17	0.0165 (12)	0.0133 (11)	0.0202 (11)	0.0020 (9)	0.0026 (9)	0.0019 (9)
C18	0.0154 (11)	0.0173 (12)	0.0192 (11)	0.0029 (9)	0.0015 (9)	0.0050 (9)
C19	0.0165 (11)	0.0203 (12)	0.0140 (10)	0.0015 (9)	0.0019 (9)	0.0027 (9)
C20	0.0123 (11)	0.0151 (12)	0.0184 (11)	0.0013 (9)	0.0009 (9)	0.0004 (9)
C21	0.0178 (12)	0.0134 (11)	0.0158 (10)	0.0040 (9)	0.0018 (9)	0.0014 (8)
C22	0.0192 (12)	0.0150 (12)	0.0162 (10)	0.0031 (9)	0.0014 (9)	0.0004 (9)
C23	0.0279 (13)	0.0156 (12)	0.0137 (10)	0.0064 (10)	−0.0008 (10)	0.0015 (9)
C24	0.0251 (13)	0.0168 (12)	0.0210 (11)	0.0028 (10)	0.0032 (10)	0.0034 (9)
C25	0.0273 (14)	0.0239 (14)	0.0238 (12)	0.0047 (11)	−0.0077 (11)	0.0006 (10)
C26	0.0438 (17)	0.0286 (15)	0.0164 (11)	0.0093 (13)	−0.0042 (11)	0.0055 (10)
C27	0.0409 (16)	0.0349 (16)	0.0209 (12)	0.0054 (13)	0.0058 (12)	0.0112 (11)
C28	0.0300 (14)	0.0258 (14)	0.0197 (12)	0.0021 (11)	0.0016 (10)	0.0030 (10)

Geometric parameters (Å, °)

Cl1—C3	1.719 (2)	C4—C5	1.401 (3)
Cl2—C4	1.714 (2)	C5—C6	1.401 (3)
Cl3—C5	1.714 (2)	C6—C7	1.382 (3)
Cl4—C6	1.722 (2)	C7—C8	1.503 (3)
Cl5—C17	1.718 (2)	C9—C10	1.375 (3)
Cl6—C18	1.717 (2)	C9—C14	1.381 (3)
Cl7—C19	1.715 (2)	C10—C11	1.380 (3)
Cl8—C20	1.725 (2)	C11—C12	1.373 (3)
F1—C10	1.344 (2)	C12—C13	1.370 (3)
F2—C11	1.344 (2)	C13—C14	1.388 (3)
F3—C12	1.350 (2)	C13—H13	0.9500
F4—C24	1.337 (2)	C14—H14	0.9500
F5—C25	1.341 (3)	C15—C16	1.499 (3)
F6—C26	1.347 (2)	C16—C17	1.382 (3)
O1—C1	1.196 (2)	C16—C21	1.387 (3)
O2—C8	1.194 (2)	C17—C18	1.408 (3)
O3—C15	1.197 (2)	C18—C19	1.398 (3)
O4—C22	1.195 (2)	C19—C20	1.404 (3)
N1—C1	1.399 (3)	C20—C21	1.380 (3)
N1—C8	1.409 (2)	C21—C22	1.501 (3)
N1—C9	1.427 (2)	C23—C28	1.371 (3)
N2—C22	1.402 (2)	C23—C24	1.378 (3)
N2—C15	1.407 (3)	C24—C25	1.389 (3)
N2—C23	1.430 (2)	C25—C26	1.366 (3)
C1—C2	1.500 (3)	C26—C27	1.374 (3)
C2—C3	1.376 (3)	C27—C28	1.393 (3)
C2—C7	1.387 (3)	C27—H27	0.9500
C3—C4	1.404 (3)	C28—H28	0.9500
C1—N1—C8	113.57 (17)	C9—C14—C13	120.1 (2)
C1—N1—C9	123.83 (18)	C9—C14—H14	120.0
C8—N1—C9	122.60 (18)	C13—C14—H14	120.0
C22—N2—C15	113.18 (17)	O3—C15—N2	125.24 (19)
C22—N2—C23	123.55 (18)	O3—C15—C16	130.1 (2)
C15—N2—C23	123.13 (18)	N2—C15—C16	104.68 (17)
O1—C1—N1	125.92 (19)	C17—C16—C21	121.68 (19)
O1—C1—C2	129.4 (2)	C17—C16—C15	129.5 (2)
N1—C1—C2	104.68 (17)	C21—C16—C15	108.75 (18)
C3—C2—C7	121.54 (19)	C16—C17—C18	117.6 (2)
C3—C2—C1	129.7 (2)	C16—C17—Cl5	121.73 (16)
C7—C2—C1	108.72 (18)	C18—C17—Cl5	120.65 (16)
C2—C3—C4	117.8 (2)	C19—C18—C17	120.79 (19)
C2—C3—Cl1	121.46 (17)	C19—C18—Cl6	119.63 (16)
C4—C3—Cl1	120.77 (16)	C17—C18—Cl6	119.54 (17)
C5—C4—C3	120.72 (19)	C18—C19—C20	120.45 (19)
C5—C4—Cl2	119.49 (16)	C18—C19—Cl7	119.97 (16)
C3—C4—Cl2	119.79 (17)	C20—C19—Cl7	119.56 (17)
C4—C5—C6	120.68 (19)	C21—C20—C19	118.1 (2)
C4—C5—Cl3	120.40 (16)	C21—C20—Cl8	120.78 (16)
C6—C5—Cl3	118.92 (17)	C19—C20—Cl8	121.09 (16)
C7—C6—C5	117.6 (2)	C20—C21—C16	121.3 (2)
C7—C6—Cl4	121.10 (17)	C20—C21—C22	130.2 (2)
C5—C6—Cl4	121.33 (17)	C16—C21—C22	108.44 (18)
C6—C7—C2	121.7 (2)	O4—C22—N2	125.79 (19)
C6—C7—C8	129.7 (2)	O4—C22—C21	129.3 (2)
C2—C7—C8	108.60 (18)	N2—C22—C21	104.91 (18)
O2—C8—N1	125.93 (19)	C28—C23—C24	120.4 (2)
O2—C8—C7	129.7 (2)	C28—C23—N2	121.9 (2)
N1—C8—C7	104.38 (18)	C24—C23—N2	117.7 (2)
C10—C9—C14	120.17 (19)	F4—C24—C23	120.94 (19)
C10—C9—N1	119.27 (19)	F4—C24—C25	119.1 (2)
C14—C9—N1	120.53 (19)	C23—C24—C25	120.0 (2)
F1—C10—C9	120.85 (19)	F5—C25—C26	121.5 (2)
F1—C10—C11	119.0 (2)	F5—C25—C24	119.6 (2)
C9—C10—C11	120.2 (2)	C26—C25—C24	118.9 (2)
F2—C11—C12	120.8 (2)	F6—C26—C25	118.4 (2)
F2—C11—C10	120.3 (2)	F6—C26—C27	119.6 (2)
C12—C11—C10	118.9 (2)	C25—C26—C27	122.0 (2)
F3—C12—C13	120.3 (2)	C26—C27—C28	118.6 (2)
F3—C12—C11	117.7 (2)	C26—C27—H27	120.7
C13—C12—C11	122.0 (2)	C28—C27—H27	120.7
C12—C13—C14	118.6 (2)	C23—C28—C27	120.0 (2)
C12—C13—H13	120.7	C23—C28—H28	120.0
C14—C13—H13	120.7	C27—C28—H28	120.0
C8—N1—C1—O1	−179.0 (2)	C22—N2—C15—O3	−178.8 (2)
C9—N1—C1—O1	1.9 (4)	C23—N2—C15—O3	−3.1 (4)
C8—N1—C1—C2	0.2 (2)	C22—N2—C15—C16	−0.4 (2)
C9—N1—C1—C2	−178.89 (19)	C23—N2—C15—C16	175.38 (19)
O1—C1—C2—C3	−2.9 (4)	O3—C15—C16—C17	−0.1 (4)
N1—C1—C2—C3	177.9 (2)	N2—C15—C16—C17	−178.4 (2)
O1—C1—C2—C7	177.5 (2)	O3—C15—C16—C21	177.4 (2)
N1—C1—C2—C7	−1.7 (2)	N2—C15—C16—C21	−0.9 (2)
C7—C2—C3—C4	−1.4 (3)	C21—C16—C17—C18	−2.9 (3)
C1—C2—C3—C4	179.1 (2)	C15—C16—C17—C18	174.3 (2)
C7—C2—C3—Cl1	179.12 (16)	C21—C16—C17—Cl5	178.95 (16)
C1—C2—C3—Cl1	−0.4 (3)	C15—C16—C17—Cl5	−3.8 (3)
C2—C3—C4—C5	0.1 (3)	C16—C17—C18—C19	1.3 (3)
Cl1—C3—C4—C5	179.60 (16)	Cl5—C17—C18—C19	179.47 (16)
C2—C3—C4—Cl2	−179.57 (16)	C16—C17—C18—Cl6	−176.17 (16)
Cl1—C3—C4—Cl2	−0.1 (3)	Cl5—C17—C18—Cl6	2.0 (3)
C3—C4—C5—C6	1.2 (3)	C17—C18—C19—C20	1.2 (3)
Cl2—C4—C5—C6	−179.15 (16)	Cl6—C18—C19—C20	178.69 (16)
C3—C4—C5—Cl3	−178.42 (16)	C17—C18—C19—Cl7	−177.29 (16)
Cl2—C4—C5—Cl3	1.3 (3)	Cl6—C18—C19—Cl7	0.2 (3)
C4—C5—C6—C7	−1.1 (3)	C18—C19—C20—C21	−2.1 (3)
Cl3—C5—C6—C7	178.44 (15)	Cl7—C19—C20—C21	176.36 (16)
C4—C5—C6—Cl4	178.15 (16)	C18—C19—C20—Cl8	179.31 (16)
Cl3—C5—C6—Cl4	−2.3 (3)	Cl7—C19—C20—Cl8	−2.2 (3)
C5—C6—C7—C2	−0.1 (3)	C19—C20—C21—C16	0.6 (3)
Cl4—C6—C7—C2	−179.42 (16)	Cl8—C20—C21—C16	179.13 (16)
C5—C6—C7—C8	178.2 (2)	C19—C20—C21—C22	−176.3 (2)
Cl4—C6—C7—C8	−1.1 (3)	Cl8—C20—C21—C22	2.2 (3)
C3—C2—C7—C6	1.4 (3)	C17—C16—C21—C20	2.0 (3)
C1—C2—C7—C6	−178.94 (19)	C15—C16—C21—C20	−175.73 (19)
C3—C2—C7—C8	−177.2 (2)	C17—C16—C21—C22	179.53 (19)
C1—C2—C7—C8	2.4 (2)	C15—C16—C21—C22	1.8 (2)
C1—N1—C8—O2	−178.4 (2)	C15—N2—C22—O4	−179.2 (2)
C9—N1—C8—O2	0.8 (4)	C23—N2—C22—O4	5.1 (4)
C1—N1—C8—C7	1.1 (2)	C15—N2—C22—C21	1.4 (2)
C9—N1—C8—C7	−179.71 (18)	C23—N2—C22—C21	−174.33 (19)
C6—C7—C8—O2	−1.2 (4)	C20—C21—C22—O4	−4.1 (4)
C2—C7—C8—O2	177.3 (2)	C16—C21—C22—O4	178.7 (2)
C6—C7—C8—N1	179.3 (2)	C20—C21—C22—N2	175.3 (2)
C2—C7—C8—N1	−2.2 (2)	C16—C21—C22—N2	−2.0 (2)
C1—N1—C9—C10	66.6 (3)	C22—N2—C23—C28	−72.5 (3)
C8—N1—C9—C10	−112.4 (2)	C15—N2—C23—C28	112.2 (3)
C1—N1—C9—C14	−115.1 (2)	C22—N2—C23—C24	107.1 (2)
C8—N1—C9—C14	65.9 (3)	C15—N2—C23—C24	−68.2 (3)
C14—C9—C10—F1	178.6 (2)	C28—C23—C24—F4	−179.3 (2)
N1—C9—C10—F1	−3.1 (3)	N2—C23—C24—F4	1.1 (3)
C14—C9—C10—C11	−2.1 (4)	C28—C23—C24—C25	0.2 (3)
N1—C9—C10—C11	176.2 (2)	N2—C23—C24—C25	−179.4 (2)
F1—C10—C11—F2	−0.2 (4)	F4—C24—C25—F5	−1.6 (3)
C9—C10—C11—F2	−179.5 (2)	C23—C24—C25—F5	178.8 (2)
F1—C10—C11—C12	−179.9 (2)	F4—C24—C25—C26	179.4 (2)
C9—C10—C11—C12	0.8 (4)	C23—C24—C25—C26	−0.1 (4)
F2—C11—C12—F3	0.4 (4)	F5—C25—C26—F6	1.8 (4)
C10—C11—C12—F3	−179.8 (2)	C24—C25—C26—F6	−179.3 (2)
F2—C11—C12—C13	−179.0 (2)	F5—C25—C26—C27	−178.8 (2)
C10—C11—C12—C13	0.7 (4)	C24—C25—C26—C27	0.1 (4)
F3—C12—C13—C14	179.7 (2)	F6—C26—C27—C28	179.2 (2)
C11—C12—C13—C14	−0.9 (4)	C25—C26—C27—C28	−0.2 (4)
C10—C9—C14—C13	2.0 (4)	C24—C23—C28—C27	−0.3 (3)
N1—C9—C14—C13	−176.3 (2)	N2—C23—C28—C27	179.3 (2)
C12—C13—C14—C9	−0.5 (4)	C26—C27—C28—C23	0.3 (4)

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O3i	0.95	2.44	3.210 (3)	138.
C27—H27···F3ii	0.95	2.45	3.379 (3)	165.
C28—H28···O1	0.95	2.50	3.403 (3)	158.

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