Azobenzene-based difunctional halogen-bond donor: towards the engineering of photoresponsive co-crystals

Halogen bonding is emerging as a powerful non-covalent interaction in the context of supramolecular photoresponsive materials design, particularly due to its high directionality. In order to obtain further insight into the solid-state features of halogen-bonded photoactive molecules, three halogen-bonded co-crystals containing an azobenzene-based difunctional halogen-bond donor molecule, (E)-bis(4-iodo-2,3,5,6-tetrafluorophenyl)diazene, C₁₂F₈I₂N₂, have been synthesized and structurally characterized by single-crystal X-ray diffraction. The crystal structure of the non-iodinated homologue (E)-bis(2,3,5,6-tetrafluorophenyl)diazene, C₁₂H₂F₈N₂, is also reported. It is demonstrated that the studied halogen-bond donor molecule is a reliable tecton for assembling halogen-bonded co-crystals with potential photoresponsive behaviour. The azo group is not involved in any specific intermolecular interactions in any of the co-crystals studied, which is an interesting feature in the context of enhanced photoisomerization behaviour and photoactive properties of the material systems.

Computing details

For all compounds, data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97.

Figures

(1)

Crystal data

C12H2F8N2	F(000) = 320
Mr = 326.16	Dx = 1.964 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9712 reflections
a = 6.2100 (8) Å	θ = 3.1–36.2°
b = 9.7294 (13) Å	µ = 0.21 mm^−1
c = 9.2163 (13) Å	T = 103 K
β = 98.019 (6)°	Block, orange
V = 551.40 (13) Å^3	0.44 × 0.22 × 0.16 mm
Z = 2

Data collection

Bruker APEX-II CCD diffractometer	2030 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
Graphite monochromator	θmax = 36.3°, θmin = 3.1°
φ and ω scans	h = −9→9
20442 measured reflections	k = −15→15
2342 independent reflections	l = −14→14

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)] = 0.032	Hydrogen site location: difference Fourier map
wR(F^2) = 0.104	All H-atom parameters refined
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0587P)^2 + 0.1154P] where P = (Fo^2 + 2Fc^2)/3
2342 reflections	(Δ/σ)max < 0.001
104 parameters	Δρmax = 0.66 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

Experimental. Bruker KRYOFLEX low temperature device.

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
F1	1.02393 (8)	0.28181 (5)	0.99996 (6)	0.02039 (12)
F2	0.71748 (9)	0.47007 (5)	0.93211 (6)	0.02319 (13)
F3	0.21506 (8)	0.12769 (5)	0.75035 (6)	0.02165 (12)
F4	0.52048 (8)	−0.06541 (5)	0.81766 (5)	0.01921 (11)
N1	0.92475 (11)	−0.01162 (7)	0.94829 (7)	0.01682 (13)
C1	0.77970 (12)	0.10003 (7)	0.91706 (7)	0.01461 (13)
C2	0.82550 (12)	0.23957 (7)	0.94339 (8)	0.01548 (13)
C3	0.66607 (13)	0.33760 (7)	0.90619 (8)	0.01698 (14)
C4	0.45784 (13)	0.30312 (8)	0.84335 (8)	0.01797 (14)
C5	0.41422 (12)	0.16611 (8)	0.81444 (8)	0.01626 (14)
C6	0.57130 (12)	0.06636 (7)	0.84808 (8)	0.01515 (13)
H4	0.350 (2)	0.3750 (13)	0.8209 (15)	0.024 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0169 (2)	0.0167 (2)	0.0266 (2)	−0.00425 (15)	−0.00006 (17)	−0.00257 (16)
F2	0.0273 (3)	0.0112 (2)	0.0314 (3)	−0.00166 (16)	0.0052 (2)	−0.00189 (17)
F3	0.0155 (2)	0.0239 (2)	0.0241 (2)	−0.00130 (17)	−0.00194 (17)	0.00046 (18)
F4	0.0205 (2)	0.0131 (2)	0.0233 (2)	−0.00318 (15)	0.00053 (16)	−0.00253 (15)
N1	0.0170 (3)	0.0141 (3)	0.0190 (3)	0.00067 (19)	0.0012 (2)	−0.0009 (2)
C1	0.0155 (3)	0.0121 (3)	0.0162 (3)	−0.0006 (2)	0.0023 (2)	−0.0010 (2)
C2	0.0152 (3)	0.0136 (3)	0.0176 (3)	−0.0020 (2)	0.0024 (2)	−0.0012 (2)
C3	0.0198 (3)	0.0118 (3)	0.0197 (3)	−0.0004 (2)	0.0041 (2)	−0.0002 (2)
C4	0.0186 (3)	0.0157 (3)	0.0198 (3)	0.0015 (2)	0.0032 (2)	0.0016 (2)
C5	0.0149 (3)	0.0169 (3)	0.0168 (3)	−0.0003 (2)	0.0015 (2)	0.0008 (2)
C6	0.0166 (3)	0.0126 (3)	0.0162 (3)	−0.0016 (2)	0.0022 (2)	−0.0008 (2)

Geometric parameters (Å, º)

F1—C2	1.3341 (9)	C1—C2	1.4013 (10)
F2—C3	1.3411 (9)	C2—C3	1.3830 (11)
F3—C5	1.3470 (9)	C3—C4	1.3825 (11)
F4—C6	1.3405 (8)	C4—C5	1.3788 (11)
N1—N1^i	1.2589 (13)	C4—H4	0.972 (13)
N1—C1	1.4149 (10)	C5—C6	1.3803 (11)
C1—C6	1.3989 (10)
N1^i—N1—C1	113.60 (8)	C5—C4—C3	117.56 (7)
C6—C1—C2	117.27 (6)	C5—C4—H4	122.9 (8)
C6—C1—N1	115.78 (6)	C3—C4—H4	119.5 (8)
C2—C1—N1	126.91 (7)	F3—C5—C4	119.78 (7)
F1—C2—C3	118.34 (6)	F3—C5—C6	118.70 (7)
F1—C2—C1	121.34 (6)	C4—C5—C6	121.52 (7)
C3—C2—C1	120.28 (7)	F4—C6—C5	119.15 (7)
F2—C3—C4	119.56 (7)	F4—C6—C1	119.66 (6)
F2—C3—C2	118.31 (7)	C5—C6—C1	121.16 (7)
C4—C3—C2	122.13 (7)
N1^i—N1—C1—C6	−156.06 (8)	C2—C3—C4—C5	−1.81 (11)
N1^i—N1—C1—C2	26.28 (12)	C3—C4—C5—F3	−178.56 (6)
C6—C1—C2—F1	−175.62 (6)	C3—C4—C5—C6	0.64 (11)
N1—C1—C2—F1	2.01 (11)	F3—C5—C6—F4	−0.77 (10)
C6—C1—C2—C3	2.13 (10)	C4—C5—C6—F4	−179.98 (7)
N1—C1—C2—C3	179.76 (7)	F3—C5—C6—C1	−178.84 (6)
F1—C2—C3—F2	−1.59 (10)	C4—C5—C6—C1	1.95 (11)
C1—C2—C3—F2	−179.41 (6)	C2—C1—C6—F4	178.65 (6)
F1—C2—C3—C4	178.22 (7)	N1—C1—C6—F4	0.75 (10)
C1—C2—C3—C4	0.39 (11)	C2—C1—C6—C5	−3.29 (10)
F2—C3—C4—C5	177.99 (7)	N1—C1—C6—C5	178.82 (6)

Symmetry code: (i) −x+2, −y, −z+2.

(2_dmso)

Crystal data

C12F8I2N2·C2H6OS	F(000) = 1224
Mr = 656.07	Dx = 2.298 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6005 reflections
a = 21.140 (3) Å	θ = 2.3–24.9°
b = 10.0766 (16) Å	µ = 3.51 mm^−1
c = 9.5589 (15) Å	T = 103 K
β = 111.347 (12)°	Lamina, orange
V = 1896.5 (5) Å^3	0.40 × 0.10 × 0.03 mm
Z = 4

Data collection

Bruker APEX-II CCD diffractometer	1662 independent reflections
Radiation source: fine-focus sealed tube	1379 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 25.0°, θmin = 3.5°
Absorption correction: multi-scan SADABS (Bruker, 2008)	h = −25→24
Tmin = 0.518, Tmax = 0.602	k = −11→11
12815 measured reflections	l = −11→10

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.065	H-atom parameters not refined
S = 1.08	w = 1/[σ^2(Fo^2) + (0.026P)^2 + 10.7129P] where P = (Fo^2 + 2Fc^2)/3
1662 reflections	(Δ/σ)max = 0.001
137 parameters	Δρmax = 0.83 e Å^−3
0 restraints	Δρmin = −1.19 e Å^−3

Special details

Experimental. Bruker KRYOFLEX low temperature device.

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	Occ. (<1)
I1	0.928736 (15)	1.17322 (3)	1.02513 (4)	0.03522 (13)
F1	0.81527 (13)	1.2003 (2)	0.6927 (3)	0.0358 (6)
F2	0.74142 (13)	1.0229 (3)	0.4973 (3)	0.0348 (6)
F3	0.84236 (15)	0.6785 (3)	0.8460 (3)	0.0418 (7)
F4	0.91586 (14)	0.8587 (3)	1.0427 (3)	0.0391 (7)
N1	0.7567 (2)	0.7375 (4)	0.5677 (4)	0.0335 (9)
C1	0.8234 (2)	1.0705 (4)	0.7321 (5)	0.0283 (10)
C2	0.7852 (2)	0.9786 (5)	0.6296 (5)	0.0302 (11)
C3	0.7914 (2)	0.8438 (4)	0.6643 (5)	0.0301 (11)
C4	0.8352 (2)	0.8074 (4)	0.8064 (5)	0.0327 (11)
C5	0.8738 (2)	0.9003 (5)	0.9066 (5)	0.0311 (11)
C6	0.8693 (2)	1.0349 (5)	0.8715 (5)	0.0312 (11)
S7	0.50223 (13)	0.9893 (2)	0.1722 (3)	0.0317 (5)	0.50
O1	0.5069 (6)	0.8464 (6)	0.2163 (9)	0.042 (3)	0.50
C7	0.5689 (4)	1.0615 (7)	0.2991 (8)	0.072 (2)
H7A	0.5625	1.1579	0.2937	0.108*	0.50
H7B	0.6099	1.0390	0.2793	0.108*	0.50
H7C	0.5736	1.0303	0.3995	0.108*	0.50
H7D	0.6015	0.9935	0.3547	0.108*	0.50
H7E	0.5541	1.1125	0.3691	0.108*	0.50
H7F	0.5904	1.1212	0.2488	0.108*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.02782 (18)	0.0385 (2)	0.0400 (2)	−0.00540 (14)	0.01311 (14)	0.00487 (15)
F1	0.0375 (15)	0.0297 (15)	0.0416 (17)	−0.0004 (11)	0.0162 (13)	0.0052 (12)
F2	0.0366 (15)	0.0330 (15)	0.0353 (16)	0.0026 (12)	0.0138 (12)	0.0043 (12)
F3	0.0627 (19)	0.0301 (15)	0.0386 (17)	0.0066 (13)	0.0256 (15)	0.0045 (12)
F4	0.0474 (17)	0.0437 (16)	0.0305 (16)	0.0084 (13)	0.0192 (13)	0.0079 (12)
N1	0.039 (2)	0.033 (2)	0.037 (2)	0.0026 (18)	0.024 (2)	0.0016 (19)
C1	0.032 (3)	0.025 (2)	0.035 (3)	0.006 (2)	0.021 (2)	0.008 (2)
C2	0.030 (2)	0.039 (3)	0.028 (3)	0.005 (2)	0.018 (2)	0.006 (2)
C3	0.036 (3)	0.032 (3)	0.033 (3)	0.001 (2)	0.024 (2)	0.001 (2)
C4	0.043 (3)	0.028 (3)	0.036 (3)	0.007 (2)	0.025 (2)	0.007 (2)
C5	0.035 (3)	0.041 (3)	0.025 (3)	0.007 (2)	0.021 (2)	0.004 (2)
C6	0.028 (3)	0.039 (3)	0.035 (3)	−0.001 (2)	0.021 (2)	−0.001 (2)
S7	0.0525 (15)	0.0210 (11)	0.0197 (11)	−0.0049 (10)	0.0108 (10)	−0.0030 (9)
O1	0.053 (6)	0.022 (3)	0.033 (8)	0.002 (3)	−0.007 (5)	0.001 (3)
C7	0.089 (5)	0.065 (4)	0.072 (5)	−0.041 (4)	0.041 (4)	−0.005 (4)

Geometric parameters (Å, º)

I1—C6	2.083 (5)	C4—C5	1.375 (7)
F1—C1	1.355 (5)	C5—C6	1.392 (7)
F2—C2	1.343 (5)	S7—O1	1.493 (6)
F3—C4	1.346 (5)	S7—C7	1.656 (7)
F4—C5	1.347 (5)	C7—H7A	0.9800
N1—N1^i	1.246 (7)	C7—H7B	0.9800
N1—C3	1.430 (6)	C7—H7C	0.9800
C1—C2	1.376 (7)	C7—H7D	0.9800
C1—C6	1.379 (6)	C7—H7E	0.9800
C2—C3	1.393 (6)	C7—H7F	0.9800
C3—C4	1.386 (7)
N1^i—N1—C3	112.9 (5)	F4—C5—C4	118.5 (4)
F1—C1—C2	118.0 (4)	F4—C5—C6	119.9 (4)
F1—C1—C6	119.6 (4)	C4—C5—C6	121.6 (4)
C2—C1—C6	122.5 (4)	C1—C6—C5	116.7 (4)
F2—C2—C1	118.2 (4)	C1—C6—I1	122.6 (3)
F2—C2—C3	121.4 (4)	C5—C6—I1	120.7 (4)
C1—C2—C3	120.4 (4)	O1—S7—C7	105.4 (5)
C4—C3—C2	117.6 (4)	H7A—C7—H7B	109.6
C4—C3—N1	115.9 (4)	H7A—C7—H7C	109.4
C2—C3—N1	126.5 (4)	H7B—C7—H7C	109.5
F3—C4—C5	118.9 (4)	H7D—C7—H7E	109.4
F3—C4—C3	119.8 (4)	H7D—C7—H7F	109.6
C5—C4—C3	121.2 (4)	H7E—C7—H7F	109.5
F1—C1—C2—F2	−0.8 (6)	N1—C3—C4—C5	176.8 (4)
C6—C1—C2—F2	179.4 (4)	F3—C4—C5—F4	−2.0 (6)
F1—C1—C2—C3	−179.9 (4)	C3—C4—C5—F4	−179.5 (4)
C6—C1—C2—C3	0.4 (7)	F3—C4—C5—C6	179.2 (4)
F2—C2—C3—C4	−176.7 (4)	C3—C4—C5—C6	1.8 (7)
C1—C2—C3—C4	2.3 (6)	F1—C1—C6—C5	178.2 (4)
F2—C2—C3—N1	3.1 (7)	C2—C1—C6—C5	−2.0 (6)
C1—C2—C3—N1	−177.9 (4)	F1—C1—C6—I1	−1.1 (6)
N1^i—N1—C3—C4	−150.3 (5)	C2—C1—C6—I1	178.7 (3)
N1^i—N1—C3—C2	29.9 (7)	F4—C5—C6—C1	−177.8 (4)
C2—C3—C4—F3	179.2 (4)	C4—C5—C6—C1	1.0 (6)
N1—C3—C4—F3	−0.6 (6)	F4—C5—C6—I1	1.6 (6)
C2—C3—C4—C5	−3.4 (7)	C4—C5—C6—I1	−179.7 (3)

Symmetry code: (i) −x+3/2, −y+3/2, −z+1.

(2_bipy)

Crystal data

C12F8I2N2·C10H8N2	F(000) = 692
Mr = 734.12	Dx = 2.244 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7724 reflections
a = 5.9388 (10) Å	θ = 2.6–34.6°
b = 8.293 (2) Å	µ = 2.98 mm^−1
c = 22.160 (4) Å	T = 103 K
β = 95.371 (12)°	Block, orange
V = 1086.6 (4) Å^3	0.40 × 0.19 × 0.10 mm
Z = 2

Data collection

Bruker APEX-II CCD diffractometer	3840 independent reflections
Radiation source: fine-focus sealed tube	3177 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 34.7°, θmin = 2.6°
Absorption correction: multi-scan SADABS (Bruker, 2008)	h = −7→8
Tmin = 0.372, Tmax = 0.442	k = −12→12
14181 measured reflections	l = −32→33

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.050	H-atom parameters not refined
S = 1.06	w = 1/[σ^2(Fo^2) + (0.015P)^2 + 1.3358P] where P = (Fo^2 + 2Fc^2)/3
3840 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 1.60 e Å^−3
0 restraints	Δρmin = −0.77 e Å^−3

Special details

Experimental. Bruker KRYOFLEX low temperature device

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
I1	0.48107 (2)	−0.005344 (15)	0.239073 (5)	0.01774 (4)
F1	0.0331 (2)	−0.19078 (15)	0.27488 (5)	0.0219 (2)
F2	−0.1805 (2)	−0.19120 (16)	0.37490 (5)	0.0231 (2)
F3	0.3923 (2)	0.14598 (15)	0.47139 (5)	0.0241 (3)
F4	0.5989 (2)	0.14730 (15)	0.37167 (5)	0.0234 (2)
N1	−0.0390 (3)	−0.0359 (2)	0.47651 (8)	0.0221 (4)
C1	0.3200 (3)	−0.0180 (2)	0.31924 (8)	0.0163 (3)
C2	0.1219 (3)	−0.1046 (2)	0.32258 (8)	0.0166 (3)
C3	0.0108 (3)	−0.1057 (2)	0.37466 (8)	0.0173 (3)
C4	0.0943 (3)	−0.0227 (2)	0.42699 (8)	0.0168 (3)
C5	0.2970 (3)	0.0616 (2)	0.42406 (8)	0.0178 (3)
C6	0.4055 (3)	0.0627 (2)	0.37143 (9)	0.0178 (3)
N2	0.7031 (3)	0.0083 (2)	0.13240 (8)	0.0260 (4)
C7	0.6291 (4)	0.0895 (3)	0.08267 (9)	0.0243 (4)
H7	0.4934	0.1500	0.0830	0.029*
C8	0.7408 (3)	0.0900 (3)	0.03015 (9)	0.0214 (4)
H8	0.6814	0.1505	−0.0041	0.026*
C9	0.9387 (3)	0.0023 (2)	0.02784 (8)	0.0166 (3)
C10	1.0161 (4)	−0.0804 (3)	0.08052 (9)	0.0237 (4)
H10	1.1521	−0.1412	0.0818	0.028*
C11	0.8951 (4)	−0.0740 (3)	0.13104 (10)	0.0272 (4)
H11	0.9519	−0.1311	0.1664	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.01949 (6)	0.02095 (6)	0.01384 (6)	−0.00101 (5)	0.00708 (4)	−0.00067 (4)
F1	0.0222 (6)	0.0314 (6)	0.0126 (5)	−0.0054 (5)	0.0033 (4)	−0.0053 (4)
F2	0.0186 (6)	0.0338 (7)	0.0175 (5)	−0.0098 (5)	0.0057 (4)	−0.0031 (5)
F3	0.0253 (7)	0.0324 (6)	0.0152 (5)	−0.0104 (5)	0.0042 (5)	−0.0083 (5)
F4	0.0207 (6)	0.0298 (6)	0.0206 (6)	−0.0100 (5)	0.0065 (5)	−0.0043 (5)
N1	0.0225 (9)	0.0301 (9)	0.0148 (7)	−0.0045 (6)	0.0072 (6)	−0.0040 (6)
C1	0.0176 (9)	0.0191 (8)	0.0130 (7)	0.0004 (6)	0.0052 (6)	0.0004 (6)
C2	0.0168 (9)	0.0215 (8)	0.0115 (7)	−0.0003 (7)	0.0009 (6)	−0.0014 (6)
C3	0.0141 (9)	0.0223 (8)	0.0158 (8)	−0.0023 (7)	0.0036 (6)	0.0001 (7)
C4	0.0170 (9)	0.0212 (9)	0.0128 (7)	0.0004 (6)	0.0050 (6)	−0.0010 (6)
C5	0.0179 (9)	0.0213 (8)	0.0143 (8)	−0.0014 (7)	0.0025 (7)	−0.0030 (7)
C6	0.0162 (9)	0.0207 (8)	0.0170 (8)	−0.0033 (7)	0.0046 (7)	−0.0004 (7)
N2	0.0265 (9)	0.0356 (10)	0.0173 (7)	−0.0045 (8)	0.0088 (7)	−0.0038 (7)
C7	0.0204 (10)	0.0306 (10)	0.0232 (10)	0.0023 (8)	0.0091 (8)	−0.0049 (8)
C8	0.0193 (10)	0.0261 (9)	0.0194 (9)	0.0037 (7)	0.0050 (7)	−0.0003 (7)
C9	0.0157 (8)	0.0202 (8)	0.0143 (7)	−0.0013 (7)	0.0035 (6)	−0.0006 (7)
C10	0.0200 (10)	0.0337 (11)	0.0179 (9)	0.0050 (8)	0.0038 (7)	0.0073 (8)
C11	0.0271 (12)	0.0370 (12)	0.0180 (9)	−0.0016 (9)	0.0046 (8)	0.0052 (8)

Geometric parameters (Å, º)

I1—C1	2.0975 (18)	C5—C6	1.384 (3)
F1—C2	1.342 (2)	N2—C7	1.331 (3)
F2—C3	1.339 (2)	N2—C11	1.332 (3)
F3—C5	1.341 (2)	C7—C8	1.393 (3)
F4—C6	1.346 (2)	C7—H7	0.9500
N1—N1^i	1.250 (3)	C8—C9	1.387 (3)
N1—C4	1.416 (2)	C8—H8	0.9500
C1—C2	1.386 (3)	C9—C10	1.394 (3)
C1—C6	1.391 (3)	C9—C9^ii	1.490 (4)
C2—C3	1.382 (3)	C10—C11	1.387 (3)
C3—C4	1.399 (3)	C10—H10	0.9500
C4—C5	1.399 (3)	C11—H11	0.9500
N1^i—N1—C4	114.7 (2)	C5—C6—C1	122.34 (18)
C2—C1—C6	116.78 (16)	C7—N2—C11	117.25 (18)
C2—C1—I1	121.85 (13)	N2—C7—C8	123.2 (2)
C6—C1—I1	121.36 (14)	N2—C7—H7	118.4
F1—C2—C3	118.11 (17)	C8—C7—H7	118.4
F1—C2—C1	120.42 (16)	C9—C8—C7	120.05 (19)
C3—C2—C1	121.47 (17)	C9—C8—H8	120.0
F2—C3—C2	118.57 (16)	C7—C8—H8	120.0
F2—C3—C4	119.48 (16)	C8—C9—C10	116.17 (17)
C2—C3—C4	121.94 (17)	C8—C9—C9^ii	121.7 (2)
C3—C4—C5	116.58 (16)	C10—C9—C9^ii	122.1 (2)
C3—C4—N1	115.08 (17)	C11—C10—C9	120.1 (2)
C5—C4—N1	128.34 (17)	C11—C10—H10	119.9
F3—C5—C6	117.36 (17)	C9—C10—H10	119.9
F3—C5—C4	121.77 (16)	N2—C11—C10	123.2 (2)
C6—C5—C4	120.86 (17)	N2—C11—H11	118.4
F4—C6—C5	117.70 (17)	C10—C11—H11	118.4
F4—C6—C1	119.95 (16)
C6—C1—C2—F1	−177.46 (17)	N1—C4—C5—C6	−179.54 (19)
I1—C1—C2—F1	3.6 (3)	F3—C5—C6—F4	0.4 (3)
C6—C1—C2—C3	2.2 (3)	C4—C5—C6—F4	179.54 (18)
I1—C1—C2—C3	−176.72 (14)	F3—C5—C6—C1	−178.82 (18)
F1—C2—C3—F2	−0.6 (3)	C4—C5—C6—C1	0.3 (3)
C1—C2—C3—F2	179.72 (17)	C2—C1—C6—F4	179.08 (17)
F1—C2—C3—C4	178.31 (17)	I1—C1—C6—F4	−2.0 (3)
C1—C2—C3—C4	−1.4 (3)	C2—C1—C6—C5	−1.7 (3)
F2—C3—C4—C5	178.80 (17)	I1—C1—C6—C5	177.24 (15)
C2—C3—C4—C5	−0.1 (3)	C11—N2—C7—C8	0.8 (3)
F2—C3—C4—N1	−1.1 (3)	N2—C7—C8—C9	0.4 (3)
C2—C3—C4—N1	−179.97 (18)	C7—C8—C9—C10	−1.2 (3)
N1^i—N1—C4—C3	178.6 (2)	C7—C8—C9—C9^ii	179.0 (2)
N1^i—N1—C4—C5	−1.2 (4)	C8—C9—C10—C11	0.9 (3)
C3—C4—C5—F3	179.71 (17)	C9^ii—C9—C10—C11	−179.3 (2)
N1—C4—C5—F3	−0.5 (3)	C7—N2—C11—C10	−1.1 (3)
C3—C4—C5—C6	0.6 (3)	C9—C10—C11—N2	0.2 (4)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···F2^iii	0.95	2.53	3.429 (3)	159
C8—H8···F3^iv	0.95	2.43	3.205 (3)	138
C10—H10···F4^v	0.95	2.46	3.316 (3)	150
C11—H11···F1^vi	0.95	2.46	3.359 (3)	158

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

(2_StOMe)

Crystal data

2(C14H13NO)·C12F8I2N2	Z = 2
Mr = 1000.45	F(000) = 976
Triclinic, P1	Dx = 1.854 Mg m^−3
a = 5.9758 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.998 (2) Å	Cell parameters from 8866 reflections
c = 21.989 (3) Å	θ = 2.2–32.3°
α = 80.264 (12)°	µ = 1.84 mm^−1
β = 88.694 (12)°	T = 103 K
γ = 81.381 (12)°	Plate, yellow
V = 1792.4 (4) Å^3	0.46 × 0.18 × 0.06 mm

Data collection

Bruker APEX-II CCD diffractometer	9283 independent reflections
Radiation source: fine-focus sealed tube	7497 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 32.5°, θmin = 2.2°
Absorption correction: multi-scan SADABS (Bruker, 2008)	h = −8→7
Tmin = 0.294, Tmax = 0.398	k = −20→20
17334 measured reflections	l = −29→32

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.073	H-atom parameters not refined
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0294P)^2 + 1.6067P] where P = (Fo^2 + 2Fc^2)/3
9283 reflections	(Δ/σ)max = 0.002
596 parameters	Δρmax = 1.53 e Å^−3
509 restraints	Δρmin = −0.64 e Å^−3

Special details

Experimental. Bruker KRYOFLEX low temperature device.

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. One of the two independent 1-(4-pyridyl)-2-phenylethylene group is disordered. It was refined with restraints, imposing the same geometry for the two components. The ADPs of atoms whose distances was less than 0.4 Å were constrained to be equal.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
I1	−0.17958 (3)	0.323393 (13)	0.138381 (8)	0.02006 (5)
F1	0.5775 (2)	0.07615 (12)	0.10441 (7)	0.0211 (3)
F2	0.3267 (2)	0.20420 (12)	0.16135 (8)	0.0229 (4)
F3	−0.2654 (2)	0.23317 (12)	0.01745 (7)	0.0207 (3)
F4	−0.0183 (2)	0.10190 (12)	−0.04003 (7)	0.0214 (3)
N1	0.3974 (3)	0.01507 (17)	−0.00678 (11)	0.0204 (5)
C1	0.3720 (4)	0.11342 (19)	0.08115 (12)	0.0165 (5)
C2	0.2396 (4)	0.18133 (19)	0.11062 (12)	0.0166 (5)
C3	0.0232 (4)	0.22427 (19)	0.09062 (12)	0.0173 (5)
C4	−0.0574 (4)	0.19423 (19)	0.03963 (12)	0.0159 (5)
C5	0.0701 (4)	0.12597 (19)	0.00983 (12)	0.0165 (5)
C6	0.2889 (4)	0.08334 (19)	0.02917 (12)	0.0163 (5)
I2	0.71377 (3)	0.216320 (13)	0.343201 (8)	0.02074 (5)
F5	0.3996 (3)	0.53838 (12)	0.44052 (8)	0.0274 (4)
F6	0.6927 (3)	0.43255 (12)	0.37829 (8)	0.0258 (4)
F7	0.2619 (3)	0.17173 (12)	0.41781 (8)	0.0263 (4)
F8	−0.0363 (3)	0.27766 (13)	0.48017 (8)	0.0287 (4)
N2	−0.0131 (4)	0.45875 (19)	0.49555 (13)	0.0288 (6)
C7	0.3586 (5)	0.4492 (2)	0.43547 (13)	0.0210 (6)
C8	0.5134 (4)	0.3933 (2)	0.40340 (13)	0.0188 (5)
C9	0.4843 (4)	0.2993 (2)	0.39505 (13)	0.0182 (5)
C10	0.2972 (4)	0.2628 (2)	0.42234 (13)	0.0202 (6)
C11	0.1410 (4)	0.3174 (2)	0.45461 (13)	0.0220 (6)
C12	0.1663 (4)	0.4123 (2)	0.46222 (13)	0.0213 (6)
O1	−0.0260 (3)	0.42275 (15)	0.96035 (10)	0.0241 (4)
N3	1.0066 (4)	−0.09297 (18)	0.72218 (12)	0.0244 (5)
C13	0.6670 (4)	0.0159 (2)	0.73791 (13)	0.0221 (6)
H13	0.5161	0.0424	0.7255	0.027*
C14	0.7930 (5)	−0.0523 (2)	0.70700 (14)	0.0234 (6)
H14	0.7245	−0.0713	0.6732	0.028*
C15	1.0994 (4)	−0.0648 (2)	0.76973 (13)	0.0222 (6)
H15	1.2508	−0.0924	0.7810	0.027*
C16	0.9869 (4)	0.0024 (2)	0.80332 (13)	0.0192 (5)
H16	1.0602	0.0195	0.8370	0.023*
C17	0.7644 (4)	0.0453 (2)	0.78764 (12)	0.0176 (5)
C18	0.6444 (4)	0.1152 (2)	0.82425 (13)	0.0193 (5)
H18	0.7245	0.1284	0.8580	0.023*
C19	0.4328 (4)	0.1621 (2)	0.81473 (13)	0.0180 (5)
H19	0.3540	0.1504	0.7803	0.022*
C20	0.3121 (4)	0.2296 (2)	0.85238 (13)	0.0179 (5)
C21	0.0915 (4)	0.2744 (2)	0.83726 (13)	0.0219 (6)
H21	0.0209	0.2594	0.8025	0.026*
C22	−0.0292 (4)	0.3402 (2)	0.87119 (13)	0.0204 (6)
H22	−0.1788	0.3700	0.8595	0.024*
C23	0.0727 (4)	0.3616 (2)	0.92259 (13)	0.0191 (5)
C24	0.2929 (4)	0.3163 (2)	0.93916 (13)	0.0190 (5)
H24	0.3616	0.3298	0.9747	0.023*
C25	0.4108 (4)	0.2524 (2)	0.90461 (13)	0.0189 (5)
H25	0.5610	0.2233	0.9162	0.023*
C26	−0.2423 (4)	0.4788 (2)	0.94241 (15)	0.0280 (7)
H26A	−0.2943	0.5197	0.9735	0.042*
H26B	−0.3517	0.4343	0.9391	0.042*
H26C	−0.2289	0.5207	0.9024	0.042*
O2	0.4479 (4)	0.95255 (16)	0.43865 (10)	0.0325 (5)
N4A	1.5291 (6)	0.4413 (3)	0.2072 (3)	0.0250 (5)	0.767 (4)
C27A	1.4206 (7)	0.5807 (3)	0.2575 (2)	0.0217 (8)	0.767 (4)
H27A	1.4544	0.6413	0.2660	0.026*	0.767 (4)
C28A	1.5648 (7)	0.5273 (3)	0.2214 (3)	0.0246 (7)	0.767 (4)
H28A	1.6969	0.5530	0.2057	0.029*	0.767 (4)
C29A	1.3446 (7)	0.4054 (3)	0.2317 (2)	0.0232 (7)	0.767 (4)
H29A	1.3191	0.3431	0.2240	0.028*	0.767 (4)
C30A	1.1895 (7)	0.4548 (3)	0.2678 (2)	0.0233 (9)	0.767 (4)
H30A	1.0595	0.4271	0.2832	0.028*	0.767 (4)
C31A	1.2248 (6)	0.5451 (3)	0.28137 (17)	0.0183 (7)	0.767 (4)
C32A	1.0551 (6)	0.5995 (3)	0.31742 (17)	0.0222 (8)	0.767 (4)
H32A	0.9357	0.5669	0.3358	0.027*	0.767 (4)
C33A	1.0579 (6)	0.6907 (3)	0.32596 (17)	0.0208 (7)	0.767 (4)
H33A	1.1865	0.7193	0.3103	0.025*	0.767 (4)
C34A	0.8874 (6)	0.7533 (3)	0.35653 (19)	0.0187 (8)	0.767 (4)
C35A	0.9156 (7)	0.8510 (3)	0.3551 (2)	0.0237 (9)	0.767 (4)
H35A	1.0425	0.8747	0.3343	0.028*	0.767 (4)
C36A	0.7621 (7)	0.9141 (3)	0.3835 (3)	0.0241 (8)	0.767 (4)
H36A	0.7847	0.9802	0.3819	0.029*	0.767 (4)
C37A	0.5751 (9)	0.8808 (4)	0.4142 (4)	0.0234 (6)	0.767 (4)
C38A	0.5412 (10)	0.7844 (3)	0.4154 (3)	0.0254 (8)	0.767 (4)
H38A	0.4123	0.7612	0.4353	0.031*	0.767 (4)
C39A	0.6975 (7)	0.7224 (3)	0.3871 (2)	0.0232 (9)	0.767 (4)
H39A	0.6742	0.6564	0.3887	0.028*	0.767 (4)
N4B	1.5352 (16)	0.4394 (9)	0.2101 (8)	0.0250 (5)	0.233 (4)
C27B	1.5010 (17)	0.5905 (9)	0.2489 (6)	0.021 (2)	0.233 (4)
H27B	1.5646	0.6477	0.2521	0.026*	0.233 (4)
C28B	1.612 (2)	0.5229 (10)	0.2154 (9)	0.0246 (7)	0.233 (4)
H28B	1.7488	0.5361	0.1952	0.029*	0.233 (4)
C29B	1.339 (2)	0.4240 (9)	0.2382 (9)	0.0232 (7)	0.233 (4)
H29B	1.2816	0.3653	0.2351	0.028*	0.233 (4)
C30B	1.2159 (18)	0.4893 (8)	0.2715 (6)	0.019 (2)	0.233 (4)
H30B	1.0765	0.4755	0.2899	0.023*	0.233 (4)
C31B	1.2967 (17)	0.5756 (7)	0.2779 (6)	0.0186 (18)	0.233 (4)
C32B	1.1728 (14)	0.6513 (8)	0.3105 (5)	0.0195 (18)	0.233 (4)
H32B	1.2485	0.7045	0.3154	0.023*	0.233 (4)
C33B	0.9677 (14)	0.6518 (8)	0.3332 (5)	0.0177 (18)	0.233 (4)
H33B	0.9005	0.5950	0.3314	0.021*	0.233 (4)
C34B	0.8279 (18)	0.7288 (7)	0.3613 (6)	0.0160 (19)	0.233 (4)
C35B	0.901 (2)	0.8202 (8)	0.3545 (8)	0.022 (2)	0.233 (4)
H35B	1.0388	0.8288	0.3334	0.027*	0.233 (4)
C36B	0.780 (2)	0.8987 (12)	0.3774 (10)	0.0241 (8)	0.233 (4)
H36B	0.8268	0.9616	0.3699	0.029*	0.233 (4)
C37B	0.588 (3)	0.8816 (12)	0.4118 (13)	0.0234 (6)	0.233 (4)
C38B	0.510 (4)	0.7916 (11)	0.4190 (12)	0.0254 (8)	0.233 (4)
H38B	0.3781	0.7808	0.4426	0.031*	0.233 (4)
C39B	0.629 (2)	0.7178 (12)	0.3911 (9)	0.024 (2)	0.233 (4)
H39B	0.5697	0.6581	0.3928	0.028*	0.233 (4)
C40	0.2671 (5)	0.9254 (3)	0.47794 (16)	0.0379 (8)
H40A	0.1872	0.9834	0.4928	0.057*
H40B	0.3279	0.8765	0.5132	0.057*
H40C	0.1616	0.8976	0.4549	0.057*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.01672 (8)	0.02013 (9)	0.02312 (10)	0.00133 (6)	0.00175 (6)	−0.00680 (8)
F1	0.0110 (7)	0.0268 (9)	0.0242 (9)	0.0034 (6)	−0.0043 (6)	−0.0058 (7)
F2	0.0179 (7)	0.0293 (9)	0.0235 (9)	−0.0012 (6)	−0.0038 (6)	−0.0113 (8)
F3	0.0124 (7)	0.0253 (8)	0.0228 (9)	0.0035 (6)	−0.0031 (6)	−0.0047 (7)
F4	0.0173 (7)	0.0277 (9)	0.0199 (8)	0.0016 (6)	−0.0039 (6)	−0.0100 (7)
N1	0.0146 (10)	0.0225 (12)	0.0237 (12)	0.0015 (8)	0.0017 (8)	−0.0063 (10)
C1	0.0096 (10)	0.0194 (13)	0.0192 (14)	0.0003 (9)	0.0002 (9)	−0.0019 (11)
C2	0.0145 (11)	0.0180 (12)	0.0173 (13)	−0.0018 (9)	−0.0012 (9)	−0.0032 (11)
C3	0.0155 (11)	0.0173 (12)	0.0185 (14)	−0.0022 (9)	0.0044 (9)	−0.0021 (11)
C4	0.0112 (11)	0.0162 (12)	0.0185 (13)	0.0004 (9)	−0.0013 (9)	0.0004 (11)
C5	0.0155 (11)	0.0187 (12)	0.0152 (13)	−0.0010 (9)	0.0004 (9)	−0.0040 (11)
C6	0.0140 (11)	0.0151 (12)	0.0187 (14)	−0.0007 (9)	0.0024 (9)	−0.0011 (11)
I2	0.01984 (9)	0.02140 (9)	0.02055 (10)	0.00298 (6)	0.00186 (6)	−0.00783 (8)
F5	0.0369 (9)	0.0170 (8)	0.0293 (10)	−0.0024 (7)	0.0010 (7)	−0.0088 (8)
F6	0.0273 (8)	0.0228 (9)	0.0277 (10)	−0.0059 (6)	0.0035 (7)	−0.0035 (8)
F7	0.0240 (8)	0.0221 (9)	0.0359 (10)	−0.0040 (6)	0.0024 (7)	−0.0133 (8)
F8	0.0219 (8)	0.0301 (10)	0.0355 (10)	−0.0032 (7)	0.0082 (7)	−0.0106 (9)
N2	0.0277 (13)	0.0270 (13)	0.0335 (15)	−0.0011 (10)	0.0036 (10)	−0.0127 (12)
C7	0.0258 (13)	0.0160 (12)	0.0212 (15)	0.0018 (10)	−0.0050 (10)	−0.0068 (12)
C8	0.0204 (12)	0.0190 (13)	0.0166 (14)	−0.0021 (10)	0.0001 (9)	−0.0023 (11)
C9	0.0175 (12)	0.0189 (13)	0.0171 (13)	0.0041 (9)	−0.0028 (9)	−0.0054 (11)
C10	0.0199 (12)	0.0204 (13)	0.0192 (14)	0.0027 (10)	−0.0013 (10)	−0.0054 (12)
C11	0.0164 (12)	0.0270 (15)	0.0229 (15)	0.0008 (10)	0.0018 (10)	−0.0085 (13)
C12	0.0215 (13)	0.0220 (14)	0.0193 (14)	0.0051 (10)	−0.0011 (10)	−0.0077 (12)
O1	0.0204 (9)	0.0250 (10)	0.0270 (11)	0.0044 (7)	−0.0019 (8)	−0.0111 (9)
N3	0.0234 (11)	0.0233 (12)	0.0268 (14)	−0.0005 (9)	0.0060 (9)	−0.0086 (11)
C13	0.0179 (12)	0.0258 (14)	0.0234 (15)	−0.0003 (10)	0.0001 (10)	−0.0090 (13)
C14	0.0232 (13)	0.0272 (15)	0.0219 (15)	−0.0029 (11)	0.0009 (10)	−0.0108 (13)
C15	0.0174 (12)	0.0243 (14)	0.0236 (15)	0.0006 (10)	0.0031 (10)	−0.0042 (12)
C16	0.0193 (12)	0.0200 (13)	0.0184 (14)	−0.0029 (10)	0.0000 (10)	−0.0036 (11)
C17	0.0177 (12)	0.0183 (13)	0.0165 (13)	−0.0021 (9)	0.0038 (9)	−0.0034 (11)
C18	0.0210 (12)	0.0207 (13)	0.0175 (14)	−0.0032 (10)	0.0004 (10)	−0.0066 (11)
C19	0.0201 (12)	0.0182 (13)	0.0167 (13)	−0.0031 (9)	−0.0004 (9)	−0.0055 (11)
C20	0.0176 (12)	0.0188 (13)	0.0168 (13)	−0.0004 (9)	0.0007 (9)	−0.0037 (11)
C21	0.0186 (12)	0.0264 (15)	0.0212 (15)	−0.0019 (10)	−0.0032 (10)	−0.0067 (12)
C22	0.0136 (11)	0.0244 (14)	0.0221 (15)	0.0012 (9)	−0.0019 (9)	−0.0041 (12)
C23	0.0201 (12)	0.0162 (12)	0.0199 (14)	0.0000 (9)	0.0017 (10)	−0.0025 (11)
C24	0.0200 (12)	0.0196 (13)	0.0170 (14)	0.0004 (9)	−0.0024 (9)	−0.0047 (11)
C25	0.0152 (11)	0.0198 (13)	0.0209 (14)	0.0007 (9)	−0.0020 (9)	−0.0042 (12)
C26	0.0182 (13)	0.0296 (16)	0.0365 (18)	0.0033 (11)	0.0027 (11)	−0.0128 (14)
O2	0.0356 (12)	0.0298 (12)	0.0302 (12)	0.0043 (9)	0.0084 (9)	−0.0083 (10)
N4A	0.0243 (11)	0.0264 (12)	0.0229 (13)	0.0050 (9)	−0.0018 (9)	−0.0079 (11)
C27A	0.021 (2)	0.0185 (16)	0.024 (2)	−0.0003 (15)	−0.0003 (16)	−0.0038 (15)
C28A	0.0223 (18)	0.0258 (15)	0.0233 (17)	0.0023 (13)	0.0009 (14)	−0.0026 (13)
C29A	0.0245 (13)	0.0236 (18)	0.0212 (17)	0.0035 (13)	−0.0010 (11)	−0.0085 (14)
C30A	0.0244 (17)	0.022 (2)	0.0238 (19)	−0.0003 (15)	−0.0016 (14)	−0.0065 (17)
C31A	0.0193 (16)	0.0181 (17)	0.0161 (16)	0.0010 (13)	0.0000 (13)	−0.0023 (15)
C32A	0.0209 (16)	0.0253 (18)	0.0185 (17)	0.0004 (13)	0.0011 (13)	−0.0023 (15)
C33A	0.0187 (16)	0.0229 (18)	0.0209 (18)	−0.0017 (13)	0.0022 (13)	−0.0055 (15)
C34A	0.0175 (16)	0.0201 (18)	0.0186 (17)	−0.0013 (13)	0.0006 (13)	−0.0045 (16)
C35A	0.0263 (17)	0.022 (2)	0.0242 (19)	−0.0026 (16)	0.0013 (14)	−0.0097 (19)
C36A	0.0293 (14)	0.0225 (18)	0.0209 (17)	0.0001 (12)	0.0043 (12)	−0.0086 (15)
C37A	0.0261 (13)	0.0246 (13)	0.0183 (14)	0.0032 (10)	0.0000 (10)	−0.0061 (11)
C38A	0.0260 (19)	0.0268 (15)	0.0218 (16)	−0.0001 (13)	0.0019 (14)	−0.0031 (13)
C39A	0.023 (2)	0.0226 (18)	0.0237 (19)	−0.0001 (16)	0.0010 (18)	−0.0060 (16)
N4B	0.0243 (11)	0.0264 (12)	0.0229 (13)	0.0050 (9)	−0.0018 (9)	−0.0079 (11)
C27B	0.020 (4)	0.024 (4)	0.020 (4)	−0.003 (4)	0.001 (4)	−0.003 (4)
C28B	0.0223 (18)	0.0258 (15)	0.0233 (17)	0.0023 (13)	0.0009 (14)	−0.0026 (13)
C29B	0.0245 (13)	0.0236 (18)	0.0212 (17)	0.0035 (13)	−0.0010 (11)	−0.0085 (14)
C30B	0.020 (4)	0.019 (4)	0.018 (4)	0.000 (3)	0.002 (3)	−0.009 (4)
C31B	0.018 (4)	0.019 (3)	0.018 (3)	−0.001 (3)	0.001 (3)	−0.003 (3)
C32B	0.021 (3)	0.020 (3)	0.015 (3)	0.005 (3)	−0.003 (3)	−0.003 (3)
C33B	0.018 (3)	0.015 (3)	0.021 (4)	−0.003 (3)	−0.003 (3)	−0.002 (3)
C34B	0.018 (4)	0.014 (3)	0.019 (3)	−0.007 (3)	−0.002 (3)	−0.007 (3)
C35B	0.023 (4)	0.022 (4)	0.022 (4)	0.003 (4)	0.004 (3)	−0.009 (4)
C36B	0.0293 (14)	0.0225 (18)	0.0209 (17)	0.0001 (12)	0.0043 (12)	−0.0086 (15)
C37B	0.0261 (13)	0.0246 (13)	0.0183 (14)	0.0032 (10)	0.0000 (10)	−0.0061 (11)
C38B	0.0260 (19)	0.0268 (15)	0.0218 (16)	−0.0001 (13)	0.0019 (14)	−0.0031 (13)
C39B	0.022 (5)	0.025 (4)	0.024 (4)	−0.008 (4)	0.000 (4)	0.000 (4)
C40	0.0234 (15)	0.059 (2)	0.0320 (18)	0.0021 (14)	0.0052 (12)	−0.0182 (18)

Geometric parameters (Å, º)

I1—C3	2.104 (2)	O2—C37A	1.345 (6)
F1—C1	1.338 (3)	O2—C37B	1.400 (19)
F2—C2	1.347 (3)	O2—C40	1.424 (4)
F3—C4	1.347 (3)	N4A—C28A	1.341 (3)
F4—C5	1.341 (3)	N4A—C29A	1.345 (3)
N1—N1^i	1.260 (4)	C27A—C28A	1.381 (4)
N1—C6	1.416 (3)	C27A—C31A	1.397 (4)
C1—C2	1.382 (3)	C27A—H27A	0.9500
C1—C6	1.408 (4)	C28A—H28A	0.9500
C2—C3	1.389 (3)	C29A—C30A	1.387 (4)
C3—C4	1.382 (4)	C29A—H29A	0.9500
C4—C5	1.376 (3)	C30A—C31A	1.394 (4)
C5—C6	1.397 (3)	C30A—H30A	0.9500
I2—C9	2.104 (2)	C31A—C32A	1.474 (4)
F5—C7	1.331 (3)	C32A—C33A	1.324 (5)
F6—C8	1.342 (3)	C32A—H32A	0.9500
F7—C10	1.343 (3)	C33A—C34A	1.469 (4)
F8—C11	1.339 (3)	C33A—H33A	0.9500
N2—N2^ii	1.236 (5)	C34A—C39A	1.393 (5)
N2—C12	1.423 (3)	C34A—C35A	1.397 (4)
C7—C8	1.380 (4)	C35A—C36A	1.389 (5)
C7—C12	1.406 (4)	C35A—H35A	0.9500
C8—C9	1.396 (4)	C36A—C37A	1.392 (4)
C9—C10	1.382 (4)	C36A—H36A	0.9500
C10—C11	1.378 (4)	C37A—C38A	1.391 (4)
C11—C12	1.397 (4)	C38A—C39A	1.387 (5)
O1—C23	1.355 (3)	C38A—H38A	0.9500
O1—C26	1.434 (3)	C39A—H39A	0.9500
N3—C15	1.337 (4)	N4B—C28B	1.342 (4)
N3—C14	1.342 (3)	N4B—C29B	1.343 (4)
C13—C14	1.387 (4)	C27B—C28B	1.379 (8)
C13—C17	1.399 (4)	C27B—C31B	1.392 (7)
C13—H13	0.9500	C27B—H27B	0.9500
C14—H14	0.9500	C28B—H28B	0.9500
C15—C16	1.380 (4)	C29B—C30B	1.382 (8)
C15—H15	0.9500	C29B—H29B	0.9500
C16—C17	1.400 (3)	C30B—C31B	1.395 (7)
C16—H16	0.9500	C30B—H30B	0.9500
C17—C18	1.466 (3)	C31B—C32B	1.477 (7)
C18—C19	1.338 (4)	C32B—C33B	1.313 (9)
C18—H18	0.9500	C32B—H32B	0.9500
C19—C20	1.460 (3)	C33B—C34B	1.474 (7)
C19—H19	0.9500	C33B—H33B	0.9500
C20—C21	1.394 (3)	C34B—C39B	1.362 (15)
C20—C25	1.407 (4)	C34B—C35B	1.396 (7)
C21—C22	1.391 (4)	C35B—C36B	1.383 (8)
C21—H21	0.9500	C35B—H35B	0.9500
C22—C23	1.393 (4)	C36B—C37B	1.391 (5)
C22—H22	0.9500	C36B—H36B	0.9500
C23—C24	1.400 (3)	C37B—C38B	1.391 (5)
C24—C25	1.375 (3)	C38B—C39B	1.386 (8)
C24—H24	0.9500	C38B—H38B	0.9500
C25—H25	0.9500	C39B—H39B	0.9500
C26—H26A	0.9800	C40—H40A	0.9800
C26—H26B	0.9800	C40—H40B	0.9800
C26—H26C	0.9800	C40—H40C	0.9800
N1^i—N1—C6	114.4 (3)	C28A—N4A—C29A	116.6 (3)
F1—C1—C2	117.9 (2)	C28A—C27A—C31A	119.7 (3)
F1—C1—C6	121.6 (2)	C28A—C27A—H27A	120.1
C2—C1—C6	120.4 (2)	C31A—C27A—H27A	120.1
F2—C2—C1	117.3 (2)	N4A—C28A—C27A	123.8 (3)
F2—C2—C3	120.0 (2)	N4A—C28A—H28A	118.1
C1—C2—C3	122.7 (2)	C27A—C28A—H28A	118.1
C4—C3—C2	116.5 (2)	N4A—C29A—C30A	123.2 (3)
C4—C3—I1	121.51 (18)	N4A—C29A—H29A	118.4
C2—C3—I1	121.92 (19)	C30A—C29A—H29A	118.4
F3—C4—C5	118.3 (2)	C29A—C30A—C31A	119.9 (4)
F3—C4—C3	119.7 (2)	C29A—C30A—H30A	120.1
C5—C4—C3	122.0 (2)	C31A—C30A—H30A	120.1
F4—C5—C4	118.4 (2)	C30A—C31A—C27A	116.7 (3)
F4—C5—C6	119.6 (2)	C30A—C31A—C32A	119.8 (3)
C4—C5—C6	121.9 (2)	C27A—C31A—C32A	123.5 (3)
C5—C6—C1	116.4 (2)	C33A—C32A—C31A	124.4 (3)
C5—C6—N1	114.8 (2)	C33A—C32A—H32A	117.8
C1—C6—N1	128.7 (2)	C31A—C32A—H32A	117.8
N2^ii—N2—C12	114.1 (3)	C32A—C33A—C34A	128.3 (4)
F5—C7—C8	117.5 (3)	C32A—C33A—H33A	115.9
F5—C7—C12	121.5 (2)	C34A—C33A—H33A	115.9
C8—C7—C12	120.9 (2)	C39A—C34A—C35A	117.1 (3)
F6—C8—C7	118.4 (2)	C39A—C34A—C33A	124.6 (3)
F6—C8—C9	119.8 (2)	C35A—C34A—C33A	118.3 (3)
C7—C8—C9	121.8 (3)	C36A—C35A—C34A	121.4 (4)
C10—C9—C8	117.0 (2)	C36A—C35A—H35A	119.3
C10—C9—I2	121.22 (19)	C34A—C35A—H35A	119.3
C8—C9—I2	121.8 (2)	C35A—C36A—C37A	120.2 (5)
F7—C10—C11	117.7 (3)	C35A—C36A—H36A	119.9
F7—C10—C9	120.3 (2)	C37A—C36A—H36A	119.9
C11—C10—C9	122.0 (3)	O2—C37A—C38A	129.3 (4)
F8—C11—C10	119.0 (3)	O2—C37A—C36A	111.2 (4)
F8—C11—C12	119.5 (2)	C38A—C37A—C36A	119.5 (5)
C10—C11—C12	121.5 (3)	C39A—C38A—C37A	119.4 (5)
C11—C12—C7	116.8 (2)	C39A—C38A—H38A	120.3
C11—C12—N2	113.9 (3)	C37A—C38A—H38A	120.3
C7—C12—N2	129.3 (2)	C38A—C39A—C34A	122.5 (4)
C23—O1—C26	117.8 (2)	C38A—C39A—H39A	118.8
C15—N3—C14	117.1 (2)	C34A—C39A—H39A	118.8
C14—C13—C17	119.3 (2)	C28B—N4B—C29B	116.9 (7)
C14—C13—H13	120.3	C28B—C27B—C31B	120.4 (9)
C17—C13—H13	120.4	C28B—C27B—H27B	119.8
N3—C14—C13	123.5 (2)	C31B—C27B—H27B	119.8
N3—C14—H14	118.2	N4B—C28B—C27B	123.1 (8)
C13—C14—H14	118.2	N4B—C28B—H28B	118.4
N3—C15—C16	123.5 (2)	C27B—C28B—H28B	118.4
N3—C15—H15	118.3	N4B—C29B—C30B	123.4 (8)
C16—C15—H15	118.3	N4B—C29B—H29B	118.3
C15—C16—C17	119.8 (2)	C30B—C29B—H29B	118.3
C15—C16—H16	120.1	C29B—C30B—C31B	119.9 (8)
C17—C16—H16	120.1	C29B—C30B—H30B	120.0
C13—C17—C16	116.9 (2)	C31B—C30B—H30B	120.0
C13—C17—C18	123.6 (2)	C27B—C31B—C30B	116.3 (7)
C16—C17—C18	119.5 (2)	C27B—C31B—C32B	119.9 (9)
C19—C18—C17	126.2 (2)	C30B—C31B—C32B	123.7 (8)
C19—C18—H18	116.9	C33B—C32B—C31B	126.0 (9)
C17—C18—H18	116.9	C33B—C32B—H32B	117.0
C18—C19—C20	126.0 (2)	C31B—C32B—H32B	117.0
C18—C19—H19	117.0	C32B—C33B—C34B	128.6 (9)
C20—C19—H19	117.0	C32B—C33B—H33B	115.7
C21—C20—C25	117.4 (2)	C34B—C33B—H33B	115.7
C21—C20—C19	120.4 (2)	C39B—C34B—C35B	118.1 (10)
C25—C20—C19	122.3 (2)	C39B—C34B—C33B	124.4 (10)
C22—C21—C20	122.5 (2)	C35B—C34B—C33B	117.5 (10)
C22—C21—H21	118.8	C36B—C35B—C34B	122.6 (13)
C20—C21—H21	118.8	C36B—C35B—H35B	118.7
C21—C22—C23	119.0 (2)	C34B—C35B—H35B	118.7
C21—C22—H22	120.5	C35B—C36B—C37B	117.2 (17)
C23—C22—H22	120.5	C35B—C36B—H36B	121.4
O1—C23—C22	125.3 (2)	C37B—C36B—H36B	121.4
O1—C23—C24	115.2 (2)	C38B—C37B—C36B	121.5 (19)
C22—C23—C24	119.5 (2)	C38B—C37B—O2	113.9 (12)
C25—C24—C23	120.7 (2)	C36B—C37B—O2	124.5 (13)
C25—C24—H24	119.6	C39B—C38B—C37B	118.7 (18)
C23—C24—H24	119.6	C39B—C38B—H38B	120.7
C24—C25—C20	120.9 (2)	C37B—C38B—H38B	120.7
C24—C25—H25	119.5	C34B—C39B—C38B	121.7 (14)
C20—C25—H25	119.5	C34B—C39B—H39B	119.2
O1—C26—H26A	109.5	C38B—C39B—H39B	119.2
O1—C26—H26B	109.5	O2—C40—H40A	109.5
H26A—C26—H26B	109.5	O2—C40—H40B	109.5
O1—C26—H26C	109.5	H40A—C40—H40B	109.5
H26A—C26—H26C	109.5	O2—C40—H40C	109.5
H26B—C26—H26C	109.5	H40A—C40—H40C	109.5
C37A—O2—C40	117.0 (3)	H40B—C40—H40C	109.5
C37B—O2—C40	120.1 (6)
F1—C1—C2—F2	−0.8 (4)	C19—C20—C21—C22	−179.1 (3)
C6—C1—C2—F2	177.7 (2)	C20—C21—C22—C23	−0.6 (5)
F1—C1—C2—C3	−179.6 (3)	C26—O1—C23—C22	−7.7 (4)
C6—C1—C2—C3	−1.1 (4)	C26—O1—C23—C24	173.9 (3)
F2—C2—C3—C4	−177.6 (2)	C21—C22—C23—O1	−178.8 (3)
C1—C2—C3—C4	1.2 (4)	C21—C22—C23—C24	−0.4 (4)
F2—C2—C3—I1	−1.2 (4)	O1—C23—C24—C25	179.8 (3)
C1—C2—C3—I1	177.6 (2)	C22—C23—C24—C25	1.3 (4)
C2—C3—C4—F3	−179.6 (2)	C23—C24—C25—C20	−1.1 (4)
I1—C3—C4—F3	3.9 (4)	C21—C20—C25—C24	0.1 (4)
C2—C3—C4—C5	−0.5 (4)	C19—C20—C25—C24	180.0 (3)
I1—C3—C4—C5	−176.9 (2)	C29A—N4A—C28A—C27A	−2.2 (8)
F3—C4—C5—F4	0.4 (4)	C31A—C27A—C28A—N4A	0.1 (8)
C3—C4—C5—F4	−178.8 (2)	C28A—N4A—C29A—C30A	3.0 (8)
F3—C4—C5—C6	178.8 (2)	N4A—C29A—C30A—C31A	−1.7 (8)
C3—C4—C5—C6	−0.3 (4)	C29A—C30A—C31A—C27A	−0.5 (6)
F4—C5—C6—C1	178.9 (2)	C29A—C30A—C31A—C32A	177.4 (4)
C4—C5—C6—C1	0.4 (4)	C28A—C27A—C31A—C30A	1.2 (6)
F4—C5—C6—N1	−1.1 (4)	C28A—C27A—C31A—C32A	−176.5 (4)
C4—C5—C6—N1	−179.5 (3)	C30A—C31A—C32A—C33A	−170.9 (4)
F1—C1—C6—C5	178.7 (2)	C27A—C31A—C32A—C33A	6.8 (6)
C2—C1—C6—C5	0.3 (4)	C31A—C32A—C33A—C34A	174.4 (4)
F1—C1—C6—N1	−1.3 (4)	C32A—C33A—C34A—C39A	5.9 (7)
C2—C1—C6—N1	−179.8 (3)	C32A—C33A—C34A—C35A	−174.0 (4)
N1^i—N1—C6—C5	172.8 (3)	C39A—C34A—C35A—C36A	0.6 (7)
N1^i—N1—C6—C1	−7.2 (5)	C33A—C34A—C35A—C36A	−179.4 (4)
F5—C7—C8—F6	−1.3 (4)	C34A—C35A—C36A—C37A	0.0 (8)
C12—C7—C8—F6	179.3 (2)	C37B—O2—C37A—C38A	−18E1 (3)
F5—C7—C8—C9	−179.4 (2)	C40—O2—C37A—C38A	8.7 (11)
C12—C7—C8—C9	1.2 (4)	C37B—O2—C37A—C36A	0E1 (3)
F6—C8—C9—C10	179.6 (2)	C40—O2—C37A—C36A	−172.3 (4)
C7—C8—C9—C10	−2.3 (4)	C35A—C36A—C37A—O2	179.8 (5)
F6—C8—C9—I2	−0.5 (4)	C35A—C36A—C37A—C38A	−1.1 (10)
C7—C8—C9—I2	177.6 (2)	O2—C37A—C38A—C39A	−179.5 (7)
C8—C9—C10—F7	−178.0 (2)	C36A—C37A—C38A—C39A	1.6 (11)
I2—C9—C10—F7	2.1 (4)	C37A—C38A—C39A—C34A	−1.0 (10)
C8—C9—C10—C11	2.2 (4)	C35A—C34A—C39A—C38A	−0.1 (7)
I2—C9—C10—C11	−177.7 (2)	C33A—C34A—C39A—C38A	179.9 (5)
F7—C10—C11—F8	0.5 (4)	C29B—N4B—C28B—C27B	1 (3)
C9—C10—C11—F8	−179.8 (3)	C31B—C27B—C28B—N4B	−2 (3)
F7—C10—C11—C12	179.2 (3)	C28B—N4B—C29B—C30B	0 (3)
C9—C10—C11—C12	−1.1 (4)	N4B—C29B—C30B—C31B	−1 (3)
F8—C11—C12—C7	178.6 (2)	C28B—C27B—C31B—C30B	1 (2)
C10—C11—C12—C7	−0.1 (4)	C28B—C27B—C31B—C32B	−176.4 (14)
F8—C11—C12—N2	−2.7 (4)	C29B—C30B—C31B—C27B	1 (2)
C10—C11—C12—N2	178.7 (3)	C29B—C30B—C31B—C32B	177.6 (14)
F5—C7—C12—C11	−179.4 (3)	C27B—C31B—C32B—C33B	171.4 (13)
C8—C7—C12—C11	0.0 (4)	C30B—C31B—C32B—C33B	−5 (2)
F5—C7—C12—N2	2.1 (5)	C31B—C32B—C33B—C34B	−174.2 (12)
C8—C7—C12—N2	−178.5 (3)	C32B—C33B—C34B—C39B	−170.9 (15)
N2^ii—N2—C12—C11	177.3 (3)	C32B—C33B—C34B—C35B	12 (2)
N2^ii—N2—C12—C7	−4.1 (5)	C39B—C34B—C35B—C36B	1 (3)
C15—N3—C14—C13	−0.2 (5)	C33B—C34B—C35B—C36B	178.1 (16)
C17—C13—C14—N3	0.2 (5)	C34B—C35B—C36B—C37B	4 (3)
C14—N3—C15—C16	0.4 (4)	C35B—C36B—C37B—C38B	−5 (3)
N3—C15—C16—C17	−0.6 (5)	C35B—C36B—C37B—O2	179 (2)
C14—C13—C17—C16	−0.3 (4)	C37A—O2—C37B—C38B	1E1 (3)
C14—C13—C17—C18	−178.6 (3)	C40—O2—C37B—C38B	10 (3)
C15—C16—C17—C13	0.5 (4)	C37A—O2—C37B—C36B	−18E1 (10)
C15—C16—C17—C18	178.8 (3)	C40—O2—C37B—C36B	−174.0 (18)
C13—C17—C18—C19	−2.1 (5)	C36B—C37B—C38B—C39B	0 (4)
C16—C17—C18—C19	179.7 (3)	O2—C37B—C38B—C39B	176 (2)
C17—C18—C19—C20	178.2 (3)	C35B—C34B—C39B—C38B	−6 (3)
C18—C19—C20—C21	179.6 (3)	C33B—C34B—C39B—C38B	177.0 (18)
C18—C19—C20—C25	−0.2 (5)	C37B—C38B—C39B—C34B	5 (3)
C25—C20—C21—C22	0.8 (4)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···F7^iii	0.95	2.62	3.492 (3)	152
C16—H16···F1^iv	0.95	2.61	3.276 (3)	127
C24—H24···F3^v	0.95	2.54	3.145 (3)	122
C25—H25···F3^v	0.95	2.51	3.132 (3)	123
C29A—H29A···F2^vi	0.95	2.56	3.451 (3)	156
C32A—H32A···F6	0.95	2.59	3.503 (3)	163
C39A—H39A···F5	0.95	2.61	3.382 (3)	139

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