Bis(2-trifluoro­methyl-1H-benzimidazol-3-ium) tetra­chloridomercurate dihydrate

In the title compound, (C₈H₆F₃N₂)₂[HgCl₄]·2H₂O, the Hg^II cation is coordinated by four Cl⁻ anions in a distorted tetra­hedral geometry. In the crystal, the 2-trifluoro­methyl-1H-benzimidazolium cations link to the [HgCl₄]²⁻ complex anions and lattice water mol­ecules via N—H...Cl and N—H...O hydrogen bonds, and the lattice water mol­ecules further link to the Hg complex anion and the organic cations via O—H...Cl and O—H...F hydrogen bonding. One of the trifluoro­methyl groups is disordered over two orientations in a 0.59 (4):0.41 (4) ratio.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.013 Å
• Disorder in main residue
• R factor = 0.053
• wR factor = 0.119
• Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C9
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Hg2
PLAT334_ALERT_2_C Small Average Benzene  C-C Dist. C11    -C16           1.37 Ang.
PLAT342_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0128 Ang
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          9
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         15

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          7
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT007_ALERT_5_G Note: Number of Unrefined D-H Atoms ............          8
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal ..........    0.03000 Deg.
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT301_ALERT_3_G Note: Main Residue  Disorder ...................          9 Perc.
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          9

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   7 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

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

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S1. Comment

Recently much attention has been devoted to simple molecular-ionic compounds containing inorganic and organic ions due to the tunability of their special structural features and their potential ferroelectrics property. Ferroelectric materials that exhibit reversible electric polarization in response to an external electric field have found many applications such as nonvolatile memory storage, electronics and optics. The freezing of a certain functional group at low temperature forces significant orientational motions of the guest molecules and thus induces the formation of the ferroelectric phase. (Fu et al, 2011; Ye et al. 2009; Zhang et al. 2009; Zhang et al. 2012; Zhang et al. 2010). In our laboratory, the title compound has been synthesized to investigate to its potentialferroelectric properties. However, it was found that the dielectric constant of the compound as a function of temperature indicates that the permittivity is basically temperature-independent (ε = C/(T–T₀)), suggesting that this compound is not ferroelectric or there may be no distinct phase transition occurring within the measured temperature (below the melting point).

The title compound,(C₈H₆F₃N₂)₂⁺.HgCl₄^2-.2H₂O, has an asymmetric unit that consists of two 2-trifluoromethyl-1H-benzimidazol cations, one tetrachloridomercuriate anion and two water molecules (Fig 1). The atoms of the benzimidazole ring are nearly coplanar and the triflouromethyl group lies out of this plane. The mercury cation is coordinated by six Cl^- anions in distorted tetrahedral geometry.the average Hg—Cl bond distances range from 2.364 (2) Å to 2.564 (2) Å, the Cl—Hg—Cl angles range from 102.24 (8)°to 120.36 (9)°. In the crystal structure, the 2-trifluoromethyl-1H-benzimidazolecations are linked to adjacent tetrachloridomercuriate anions and watermolecules by N—H···O, N—H···Cl and O—H···Cl hydrogen bonds to form one dimensional chains parallel to ac plane (Fig 2). One of the trifluoromethyl is disordered.

Related literature

For background to ferroelectric complexes, see: Fu et al. (2011); Ye et al. (2009). Zhang et al. (2009, 2010, 2012). For related structures, see: Liu (2011a,b, 2012a,b,c).

S2. Experimental

0.144 g (1 mmol) of 2-trifluoromethyl-1H-benzimidazol was firstly dissolved in 30 ml of ethanol which was added hydrochloric acid, to which 0.271 g (1 mmol) of mercuric chloride was added to give a solution at the ambient temperature. Single crystals suitable for X-ray structure analysis were obtained by the slow evaporation of the above solution after 5 days in air.

S3. Refinement

H atoms were placed in calculated positions (O—H = 0.85 Å; N—H = 0.89 Å; C—H = 0.93Å for Csp² atoms and C—H = 0.96Å and 0.97Å for Csp³ atoms), assigned fixed U_iso values [U_iso = 1.2Ueq(Csp²) and 1.5Ueq(Csp³,N,O)] and allowed to ride. The trifluoromethyl group is disordered over two sites. The site occupancies were refined and restraints were applied to the thermal parameters.

Computing details

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures

	Fig. 1. The molecular structure of the title compound, showing the atomic numbering scheme with 30% probability displacement ellipsoids.
	Fig. 2. The packing of the title compound with view along the b axis. For the sake of clarity only the major component of the disordered trifluoromethyl group is shown.

Bis(2-trifluoromethyl-1H-benzimidazol-3-ium) tetrachloridomercurate dihydrate

Crystal data

(C8H6F3N2)2[HgCl4]·2H2O	Z = 2
Mr = 752.72	F(000) = 716
Triclinic, P1	Dx = 2.047 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2485 (18) Å	Cell parameters from 4366 reflections
b = 10.029 (2) Å	θ = 3.0–26.0°
c = 14.754 (3) Å	µ = 6.81 mm^−1
α = 79.40 (3)°	T = 293 K
β = 75.79 (3)°	Block, colourless
γ = 67.74 (3)°	0.36 × 0.32 × 0.28 mm
V = 1221.4 (4) Å^3

Data collection

Rigaku SCXmini diffractometer	5564 independent reflections
Radiation source: fine-focus sealed tube	4040 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
CCD_Profile_fitting scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −12→12
Tmin = 0.095, Tmax = 0.152	k = −13→12
12786 measured reflections	l = −19→19

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.119	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0373P)^2 + 1.355P] where P = (Fo^2 + 2Fc^2)/3
5564 reflections	(Δ/σ)max = 0.022
326 parameters	Δρmax = 0.57 e Å^−3
9 restraints	Δρmin = −1.28 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. 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 > 2sigma(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	Occ. (<1)
F1	0.7017 (13)	0.721 (2)	0.7840 (6)	0.093 (6)	0.59 (4)
F2	0.499 (3)	0.677 (2)	0.8538 (16)	0.123 (10)	0.59 (4)
F3	0.535 (3)	0.8571 (9)	0.8821 (10)	0.112 (9)	0.59 (4)
F1'	0.656 (4)	0.652 (3)	0.7911 (14)	0.137 (16)	0.41 (4)
F3'	0.639 (4)	0.841 (2)	0.843 (3)	0.16 (2)	0.41 (4)
F2'	0.4537 (9)	0.751 (3)	0.8841 (12)	0.102 (11)	0.41 (4)
N1	0.7197 (6)	0.4910 (6)	0.9609 (4)	0.0463 (14)
H1A	0.6964	0.4371	0.9319	0.056*
N2	0.7409 (6)	0.6807 (6)	0.9988 (4)	0.0446 (13)
H2A	0.7328	0.7692	0.9978	0.053*
C1	0.6080 (8)	0.7210 (7)	0.8664 (5)	0.064 (2)
C2	0.6894 (8)	0.6313 (8)	0.9408 (5)	0.0446 (16)
C3	0.7956 (7)	0.4460 (7)	1.0370 (5)	0.0392 (15)
C4	0.8554 (9)	0.3110 (8)	1.0833 (5)	0.0522 (18)
H4	0.8479	0.2294	1.0662	0.063*
C5	0.9278 (9)	0.3035 (8)	1.1571 (5)	0.0532 (18)
H5	0.9701	0.2150	1.1913	0.064*
C6	0.9371 (8)	0.4285 (9)	1.1801 (5)	0.0535 (18)
H6	0.9860	0.4200	1.2300	0.064*
C7	0.8793 (8)	0.5611 (8)	1.1340 (5)	0.0456 (16)
H7	0.8871	0.6425	1.1511	0.055*
C8	0.8083 (7)	0.5692 (7)	1.0604 (5)	0.0376 (14)
F4	0.2353 (11)	0.1121 (7)	0.5538 (6)	0.146 (3)
F5	0.3648 (10)	0.1573 (10)	0.4248 (7)	0.167 (4)
F6	0.1251 (8)	0.2625 (7)	0.4538 (6)	0.124 (2)
N3	0.3498 (7)	0.3080 (7)	0.5958 (4)	0.0579 (16)
H3A	0.3878	0.2271	0.6286	0.070*
N4	0.2323 (7)	0.4628 (7)	0.4921 (4)	0.0526 (15)
H4A	0.1822	0.4993	0.4462	0.063*
C9	0.2500 (13)	0.2136 (11)	0.4902 (7)	0.076 (3)
C10	0.2768 (8)	0.3277 (8)	0.5263 (5)	0.0503 (17)
C11	0.3561 (8)	0.4384 (9)	0.6076 (5)	0.0516 (18)
C12	0.4205 (10)	0.4786 (14)	0.6680 (6)	0.079 (3)
H12	0.4753	0.4119	0.7117	0.095*
C13	0.3997 (13)	0.6218 (17)	0.6601 (8)	0.097 (4)
H13	0.4396	0.6534	0.7008	0.116*
C14	0.3236 (14)	0.7196 (14)	0.5960 (9)	0.098 (4)
H14	0.3153	0.8155	0.5935	0.117*
C15	0.2581 (11)	0.6842 (10)	0.5344 (7)	0.072 (2)
H15	0.2037	0.7525	0.4912	0.086*
C16	0.2792 (9)	0.5380 (9)	0.5415 (5)	0.0524 (18)
Hg2	0.11556 (4)	0.82505 (3)	0.24321 (2)	0.05631 (13)
Cl1	0.0685 (3)	0.6016 (2)	0.32320 (13)	0.0606 (5)
Cl2	0.3673 (3)	0.7252 (2)	0.11954 (14)	0.0653 (5)
Cl3	−0.1015 (4)	0.9354 (3)	0.1548 (2)	0.1100 (11)
Cl4	0.1746 (4)	0.9720 (3)	0.32658 (19)	0.1004 (9)
O1	0.2620 (9)	0.0518 (6)	1.0084 (5)	0.099 (2)
H1C	0.3067	0.0060	0.9601	0.148*
H1B	0.2751	−0.0072	1.0576	0.148*
O2	0.4458 (11)	0.0872 (10)	0.7187 (7)	0.166 (4)
H2B	0.5002	0.0086	0.6939	0.249*
H2D	0.3630	0.0783	0.7558	0.249*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.066 (7)	0.132 (15)	0.054 (7)	−0.020 (8)	−0.006 (5)	0.016 (7)
F2	0.085 (14)	0.187 (19)	0.124 (17)	−0.076 (13)	−0.071 (14)	0.047 (14)
F3	0.130 (16)	0.066 (9)	0.099 (9)	0.029 (8)	−0.054 (10)	0.000 (7)
F1'	0.11 (3)	0.20 (3)	0.055 (12)	0.015 (19)	−0.030 (13)	−0.034 (13)
F3'	0.15 (3)	0.16 (3)	0.21 (4)	−0.10 (2)	−0.13 (3)	0.13 (3)
F2'	0.041 (8)	0.17 (3)	0.056 (9)	−0.001 (11)	−0.007 (7)	0.001 (12)
N1	0.040 (3)	0.054 (4)	0.053 (3)	−0.023 (3)	−0.011 (3)	−0.007 (3)
N2	0.037 (3)	0.032 (3)	0.061 (4)	−0.011 (2)	−0.009 (3)	0.001 (3)
C1	0.060 (6)	0.069 (6)	0.057 (5)	−0.020 (5)	−0.013 (4)	0.007 (5)
C2	0.031 (4)	0.050 (4)	0.050 (4)	−0.016 (3)	−0.002 (3)	−0.002 (3)
C3	0.031 (3)	0.037 (4)	0.047 (4)	−0.011 (3)	−0.001 (3)	−0.009 (3)
C4	0.046 (4)	0.048 (4)	0.067 (5)	−0.024 (4)	−0.005 (4)	−0.007 (4)
C5	0.053 (5)	0.047 (4)	0.054 (4)	−0.017 (4)	−0.008 (4)	0.004 (4)
C6	0.037 (4)	0.069 (5)	0.054 (4)	−0.022 (4)	−0.002 (3)	−0.005 (4)
C7	0.039 (4)	0.051 (4)	0.050 (4)	−0.019 (3)	−0.002 (3)	−0.016 (3)
C8	0.028 (3)	0.039 (3)	0.045 (4)	−0.014 (3)	0.002 (3)	−0.006 (3)
F4	0.238 (10)	0.076 (4)	0.153 (6)	−0.092 (5)	−0.050 (6)	0.011 (4)
F5	0.130 (6)	0.189 (8)	0.213 (9)	−0.090 (6)	0.056 (6)	−0.144 (7)
F6	0.119 (5)	0.108 (5)	0.188 (7)	−0.048 (4)	−0.078 (5)	−0.035 (5)
N3	0.041 (4)	0.063 (4)	0.059 (4)	−0.012 (3)	−0.014 (3)	0.013 (3)
N4	0.057 (4)	0.065 (4)	0.044 (3)	−0.031 (3)	−0.017 (3)	0.005 (3)
C9	0.078 (7)	0.074 (6)	0.085 (7)	−0.035 (5)	−0.005 (6)	−0.022 (6)
C10	0.037 (4)	0.054 (4)	0.055 (4)	−0.014 (3)	−0.010 (3)	0.003 (4)
C11	0.038 (4)	0.080 (5)	0.040 (4)	−0.027 (4)	−0.006 (3)	0.002 (4)
C12	0.047 (5)	0.137 (10)	0.056 (5)	−0.038 (6)	0.000 (4)	−0.015 (6)
C13	0.080 (8)	0.163 (13)	0.074 (7)	−0.069 (8)	0.011 (6)	−0.055 (8)
C14	0.100 (9)	0.119 (9)	0.101 (8)	−0.078 (8)	0.019 (7)	−0.040 (8)
C15	0.065 (6)	0.079 (6)	0.075 (6)	−0.037 (5)	−0.003 (5)	−0.008 (5)
C16	0.044 (4)	0.067 (5)	0.054 (4)	−0.032 (4)	−0.004 (4)	−0.007 (4)
Hg2	0.0667 (2)	0.0587 (2)	0.05325 (19)	−0.03158 (16)	−0.01580 (15)	−0.00235 (14)
Cl1	0.0810 (14)	0.0633 (12)	0.0535 (11)	−0.0420 (11)	−0.0290 (10)	0.0135 (9)
Cl2	0.0645 (13)	0.0756 (13)	0.0635 (12)	−0.0374 (11)	0.0002 (10)	−0.0144 (11)
Cl3	0.133 (3)	0.0746 (16)	0.155 (3)	−0.0507 (17)	−0.103 (2)	0.0420 (17)
Cl4	0.158 (3)	0.0916 (18)	0.0906 (17)	−0.0746 (19)	−0.0426 (18)	−0.0120 (15)
O1	0.142 (7)	0.050 (3)	0.112 (5)	−0.033 (4)	−0.048 (5)	0.006 (4)
O2	0.122 (7)	0.135 (7)	0.152 (8)	0.018 (6)	−0.038 (6)	0.076 (7)

Geometric parameters (Å, º)

F1—C1	1.308 (2)	N3—C10	1.308 (9)
F2—C1	1.309 (2)	N3—C11	1.375 (10)
F3—C1	1.309 (2)	N3—H3A	0.8599
F1'—C1	1.309 (2)	N4—C10	1.300 (9)
F3'—C1	1.309 (2)	N4—C16	1.376 (9)
F2'—C1	1.309 (2)	N4—H4A	0.8601
N1—C2	1.317 (9)	C9—C10	1.469 (11)
N1—C3	1.386 (8)	C11—C16	1.377 (10)
N1—H1A	0.8600	C11—C12	1.374 (12)
N2—C2	1.318 (8)	C12—C13	1.361 (15)
N2—C8	1.357 (8)	C12—H12	0.9300
N2—H2A	0.8600	C13—C14	1.347 (16)
C1—C2	1.453 (10)	C13—H13	0.9300
C3—C4	1.371 (9)	C14—C15	1.368 (14)
C3—C8	1.395 (8)	C14—H14	0.9300
C4—C5	1.390 (10)	C15—C16	1.391 (11)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.395 (10)	Hg2—Cl4	2.364 (2)
C5—H5	0.9300	Hg2—Cl3	2.455 (3)
C6—C7	1.350 (10)	Hg2—Cl1	2.4734 (19)
C6—H6	0.9300	Hg2—Cl2	2.564 (2)
C7—C8	1.377 (9)	O1—H1C	0.8500
C7—H7	0.9300	O1—H1B	0.8500
F4—C9	1.274 (11)	O2—H2B	0.8500
F5—C9	1.274 (11)	O2—H2D	0.8500
F6—C9	1.281 (11)
C2—N1—C3	107.7 (6)	N2—C8—C3	106.5 (6)
C2—N1—H1A	126.1	C7—C8—C3	120.8 (6)
C3—N1—H1A	126.2	C10—N3—C11	108.6 (6)
C2—N2—C8	108.9 (6)	C10—N3—H3A	125.8
C2—N2—H2A	125.6	C11—N3—H3A	125.7
C8—N2—H2A	125.5	C10—N4—C16	108.4 (6)
F1—C1—F2'	127.4 (10)	C10—N4—H4A	125.9
F1—C1—F3'	68.6 (15)	C16—N4—H4A	125.7
F2'—C1—F3'	109.5 (15)	F4—C9—F5	107.8 (10)
F1—C1—F3	106.1 (10)	F4—C9—F6	107.4 (9)
F2'—C1—F3	70.4 (12)	F5—C9—F6	105.6 (10)
F1—C1—F2	104.5 (11)	F4—C9—C10	112.6 (9)
F3'—C1—F2	135.0 (11)	F5—C9—C10	110.9 (8)
F3—C1—F2	105.9 (12)	F6—C9—C10	112.3 (8)
F2'—C1—F1'	103.1 (16)	N4—C10—N3	110.6 (7)
F3'—C1—F1'	107.4 (18)	N4—C10—C9	124.1 (8)
F3—C1—F1'	134.0 (13)	N3—C10—C9	125.2 (8)
F2—C1—F1'	68.8 (14)	N3—C11—C16	105.9 (6)
F1—C1—C2	113.7 (8)	N3—C11—C12	132.9 (9)
F2'—C1—C2	115.1 (9)	C16—C11—C12	121.2 (9)
F3'—C1—C2	111.0 (9)	C13—C12—C11	116.1 (10)
F3—C1—C2	113.6 (7)	C13—C12—H12	121.9
F2—C1—C2	112.1 (7)	C11—C12—H12	121.9
F1'—C1—C2	110.1 (9)	C14—C13—C12	122.8 (10)
N1—C2—N2	110.7 (6)	C14—C13—H13	118.6
N1—C2—C1	125.2 (6)	C12—C13—H13	118.6
N2—C2—C1	124.1 (6)	C13—C14—C15	123.0 (11)
C4—C3—N1	130.9 (6)	C13—C14—H14	118.5
C4—C3—C8	122.9 (6)	C15—C14—H14	118.5
N1—C3—C8	106.2 (6)	C14—C15—C16	114.7 (10)
C3—C4—C5	116.0 (6)	C14—C15—H15	122.6
C3—C4—H4	122.0	C16—C15—H15	122.6
C5—C4—H4	122.0	C11—C16—N4	106.5 (7)
C4—C5—C6	120.1 (7)	C11—C16—C15	122.1 (8)
C4—C5—H5	119.9	N4—C16—C15	131.4 (8)
C6—C5—H5	119.9	Cl4—Hg2—Cl3	119.35 (10)
C7—C6—C5	123.8 (7)	Cl4—Hg2—Cl1	120.36 (8)
C7—C6—H6	118.1	Cl3—Hg2—Cl1	102.26 (8)
C5—C6—H6	118.1	Cl4—Hg2—Cl2	105.49 (10)
C6—C7—C8	116.4 (6)	Cl3—Hg2—Cl2	105.13 (11)
C6—C7—H7	121.8	Cl1—Hg2—Cl2	102.10 (8)
C8—C7—H7	121.8	H1C—O1—H1B	109.5
N2—C8—C7	132.7 (6)	H2B—O2—H2D	109.5
C3—N1—C2—N2	0.2 (8)	N1—C3—C8—N2	0.0 (7)
C3—N1—C2—C1	−178.8 (6)	C4—C3—C8—C7	−1.7 (10)
C8—N2—C2—N1	−0.2 (8)	N1—C3—C8—C7	−179.9 (6)
C8—N2—C2—C1	178.9 (6)	C16—N4—C10—N3	0.3 (8)
F1—C1—C2—N1	−84.6 (15)	C16—N4—C10—C9	−178.9 (8)
F2'—C1—C2—N1	75.3 (19)	C11—N3—C10—N4	−0.9 (9)
F3'—C1—C2—N1	−160 (2)	C11—N3—C10—C9	178.3 (8)
F3—C1—C2—N1	153.8 (14)	F4—C9—C10—N4	−150.4 (9)
F2—C1—C2—N1	33.7 (19)	F5—C9—C10—N4	88.8 (12)
F1'—C1—C2—N1	−41 (3)	F6—C9—C10—N4	−29.0 (13)
F1—C1—C2—N2	96.5 (14)	F4—C9—C10—N3	30.4 (13)
F2'—C1—C2—N2	−103.6 (17)	F5—C9—C10—N3	−90.4 (12)
F3'—C1—C2—N2	22 (2)	F6—C9—C10—N3	151.8 (9)
F3—C1—C2—N2	−25.1 (14)	C10—N3—C11—C16	1.1 (8)
F2—C1—C2—N2	−145.2 (16)	C10—N3—C11—C12	−178.6 (8)
F1'—C1—C2—N2	140 (2)	N3—C11—C12—C13	−178.5 (8)
C2—N1—C3—C4	−178.1 (7)	C16—C11—C12—C13	1.8 (12)
C2—N1—C3—C8	−0.1 (7)	C11—C12—C13—C14	−1.4 (15)
N1—C3—C4—C5	178.9 (7)	C12—C13—C14—C15	1.3 (17)
C8—C3—C4—C5	1.3 (10)	C13—C14—C15—C16	−1.4 (15)
C3—C4—C5—C6	−0.3 (10)	N3—C11—C16—N4	−0.9 (8)
C4—C5—C6—C7	−0.2 (11)	C12—C11—C16—N4	178.8 (7)
C5—C6—C7—C8	−0.2 (10)	N3—C11—C16—C15	178.1 (7)
C2—N2—C8—C7	180.0 (7)	C12—C11—C16—C15	−2.2 (12)
C2—N2—C8—C3	0.1 (7)	C10—N4—C16—C11	0.4 (8)
C6—C7—C8—N2	−178.8 (7)	C10—N4—C16—C15	−178.5 (8)
C6—C7—C8—C3	1.1 (9)	C14—C15—C16—C11	1.9 (12)
C4—C3—C8—N2	178.2 (6)	C14—C15—C16—N4	−179.5 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl2^i	0.86	2.23	3.081 (6)	170
N2—H2A···O1^ii	0.86	1.80	2.656 (8)	174
N3—H3A···O2	0.86	1.76	2.608 (9)	166
N4—H4A···Cl1	0.86	2.21	3.069 (6)	175
O1—H1C···F3^iii	0.85	2.25	2.994 (18)	146
O1—H1B···Cl2^iv	0.85	2.55	3.279 (6)	144
O2—H2B···F5^v	0.85	2.41	3.224 (13)	160
O2—H2D···Cl3^vi	0.85	2.50	3.339 (10)	172

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