Color-tunable phosphorescence of 1,10-phenanthrolines by 4,7-methyl/-diphenyl/-dichloro substituents in cocrystals assembled via bifurcated C—I...N halogen bonds using 1,4-diiodotetrafluorobenzene as a bonding donor

Single-crystal X-ray diffraction reveals a series of phosphorescent cocrystals which were assembled by 1,4-diiodotetrafluorobenzene (1,4-DITFB) and either 4,7-dimethyl-1,10-phenanthroline (DMPhe), 4,7-diphenyl-1,10-phenanthroline (DPPhe) or 4,7-dichloro-1,10-phenanthroline (DClPhe) via C—I...N halogen bonding. These cocrystals, labeled (1), (2) and (3), respectively, are phosphorescent and a distinct change in phosphorescent color can be observed from orange–yellow, green to yellow–green, with well defined vibrational band maxima at 587, 520 and 611 nm for (1), (2) and (3). Based on the dependence of halogen bonding in sites and strength, we discussed the impact of substituents with different electron-withdrawing effects and steric hindrance on intermolecular noncovalent interactions and phosphorescence. The method of inducing and modulating phosphorescence by halogen bonding and other weak non-covalent interactions through changing the substituent groups of molecules should be significant in both theory and the application of optical function materials with predictable and modulated luminescent properties.

Computing details

For all compounds, data collection: Bruker APEX2; cell refinement: Bruker SAINT; data reduction: Bruker SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Bruker SHELXTL; software used to prepare material for publication: Bruker SHELXTL.

(160411a_0m)

Crystal data

C33H18F8I4N3	F(000) = 4168
Mr = 1116.10	Dx = 2.145 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.455 (4) Å	Cell parameters from 656 reflections
b = 27.777 (10) Å	θ = 2.6–17.9°
c = 21.823 (9) Å	µ = 3.68 mm^−1
β = 95.607 (9)°	T = 296 K
V = 6911 (4) Å^3	Block, pale-yellow
Z = 8	0.17 × 0.11 × 0.10 mm

Data collection

Bruker APEX-II CCD diffractometer	7926 independent reflections
Radiation source: fine-focus sealed tube	2398 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.165
φ and ω scans	θmax = 27.5°, θmin = 1.5°
Absorption correction: multi-scan SADABS	h = −14→14
Tmin = 0.574, Tmax = 0.710	k = −32→36
22301 measured reflections	l = −19→28

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 0.87	w = 1/[σ^2(Fo^2) + (0.030P)^2] where P = (Fo^2 + 2Fc^2)/3
7926 reflections	(Δ/σ)max < 0.001
435 parameters	Δρmax = 1.10 e Å^−3
0 restraints	Δρmin = −1.42 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
C1	0.4925 (9)	0.1804 (4)	0.3335 (6)	0.037 (3)
C2	0.5114 (11)	0.1311 (5)	0.3330 (6)	0.048 (4)
C3	0.4230 (11)	0.0994 (4)	0.3144 (7)	0.060 (4)
C4	0.3093 (9)	0.1148 (4)	0.2915 (6)	0.040 (3)
C5	0.2935 (10)	0.1643 (4)	0.2888 (6)	0.045 (4)
C6	0.3817 (11)	0.1953 (4)	0.3106 (6)	0.046 (4)
C7	0.1114 (11)	0.1905 (5)	0.4106 (7)	0.051 (4)
C8	0.2185 (14)	0.2102 (5)	0.4297 (7)	0.065 (5)
C9	0.3112 (13)	0.1818 (7)	0.4577 (7)	0.074 (5)
C10	0.2988 (12)	0.1327 (6)	0.4620 (7)	0.063 (4)
C11	0.1924 (13)	0.1126 (6)	0.4422 (7)	0.068 (5)
C12	0.1017 (12)	0.1421 (5)	0.4153 (7)	0.057 (4)
C13	0.1562 (11)	0.3085 (5)	0.2524 (7)	0.056 (4)
H13	0.1459	0.2784	0.2697	0.067*
C14	0.1473 (10)	0.3475 (5)	0.2888 (7)	0.059 (4)
H14	0.1317	0.3442	0.3297	0.071*
C15	0.1624 (10)	0.3928 (5)	0.2632 (8)	0.052 (4)
C16	0.1455 (10)	0.4359 (5)	0.3055 (7)	0.068 (4)
H16A	0.1320	0.4245	0.3457	0.103*
H16B	0.0792	0.4546	0.2888	0.103*
H16C	0.2146	0.4557	0.3084	0.103*
C17	0.1831 (10)	0.3977 (5)	0.2033 (8)	0.048 (4)
C18	0.1948 (11)	0.4422 (4)	0.1739 (7)	0.055 (4)
H18	0.1855	0.4706	0.1954	0.066*
C19	0.2196 (10)	0.4443 (5)	0.1140 (7)	0.058 (4)
H19	0.2249	0.4742	0.0955	0.070*
C20	0.2378 (9)	0.4021 (4)	0.0785 (7)	0.041 (3)
C21	0.2655 (11)	0.4033 (5)	0.0172 (7)	0.054 (4)
C22	0.2724 (11)	0.4506 (5)	−0.0160 (7)	0.078 (5)
H22A	0.2816	0.4447	−0.0586	0.118*
H22B	0.3384	0.4687	0.0022	0.118*
H22C	0.2017	0.4686	−0.0127	0.118*
C23	0.2810 (11)	0.3601 (6)	−0.0122 (7)	0.067 (5)
H23	0.2981	0.3591	−0.0530	0.081*
C24	0.2699 (11)	0.3179 (5)	0.0218 (8)	0.064 (5)
H24	0.2809	0.2890	0.0016	0.077*
C25	0.2243 (9)	0.3575 (5)	0.1081 (7)	0.044 (4)
C26	0.1976 (10)	0.3543 (5)	0.1690 (7)	0.045 (4)
C27	0.4879 (9)	0.4450 (4)	0.2820 (5)	0.035 (3)
C28	0.4739 (9)	0.4008 (4)	0.3128 (6)	0.033 (3)
C29	0.4500 (10)	0.4007 (5)	0.3742 (7)	0.053 (4)
C30	0.4391 (10)	0.4458 (5)	0.4018 (7)	0.054 (4)
H30	0.4200	0.4480	0.4421	0.065*
C31	0.4574 (10)	0.4874 (5)	0.3680 (8)	0.060 (4)
H31	0.4559	0.5168	0.3885	0.072*
C32	0.4870 (10)	0.3570 (4)	0.2787 (6)	0.046 (4)
H32	0.4767	0.3277	0.2980	0.055*
C33	0.4295 (11)	0.3560 (4)	0.4094 (7)	0.074 (5)
H33A	0.3561	0.3419	0.3938	0.111*
H33B	0.4274	0.3638	0.4522	0.111*
H33C	0.4918	0.3336	0.4051	0.111*
F1	0.6160 (6)	0.1132 (2)	0.3547 (4)	0.069 (3)
F2	0.4469 (6)	0.0519 (2)	0.3174 (4)	0.072 (3)
F3	0.1877 (5)	0.1811 (2)	0.2698 (4)	0.059 (2)
F4	0.3568 (6)	0.2425 (2)	0.3082 (4)	0.065 (2)
F5	0.2361 (6)	0.2577 (3)	0.4273 (4)	0.091 (3)
F6	0.4123 (7)	0.2036 (4)	0.4757 (5)	0.117 (4)
F7	0.1749 (7)	0.0655 (3)	0.4453 (5)	0.102 (3)
F8	0.0003 (6)	0.1202 (2)	0.3965 (4)	0.078 (3)
I1	0.62177 (7)	0.23024 (3)	0.35990 (5)	0.0548 (3)
I2	0.17799 (7)	0.06692 (3)	0.26217 (6)	0.0679 (4)
I3	−0.02562 (7)	0.23528 (3)	0.37571 (5)	0.0627 (3)
I4	0.43465 (11)	0.09201 (6)	0.50263 (7)	0.1477 (7)
N1	0.1783 (9)	0.3098 (4)	0.1941 (6)	0.053 (3)
N2	0.2458 (9)	0.3151 (4)	0.0784 (6)	0.050 (3)
N3	0.4767 (9)	0.4883 (4)	0.3092 (6)	0.055 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.037 (7)	0.043 (8)	0.034 (9)	−0.001 (6)	0.013 (7)	0.008 (6)
C2	0.054 (9)	0.049 (9)	0.038 (10)	0.010 (7)	−0.009 (8)	0.002 (7)
C3	0.064 (9)	0.025 (8)	0.088 (14)	−0.010 (7)	−0.005 (9)	0.001 (8)
C4	0.039 (7)	0.031 (7)	0.049 (10)	0.005 (6)	0.001 (7)	−0.001 (7)
C5	0.038 (8)	0.047 (9)	0.050 (10)	−0.007 (7)	0.002 (7)	0.003 (7)
C6	0.071 (10)	0.022 (7)	0.046 (10)	0.006 (7)	0.013 (8)	0.002 (7)
C7	0.046 (8)	0.050 (9)	0.057 (11)	0.001 (7)	0.006 (8)	−0.004 (8)
C8	0.074 (11)	0.061 (11)	0.064 (13)	−0.019 (9)	0.026 (10)	−0.006 (9)
C9	0.049 (10)	0.119 (16)	0.052 (13)	−0.009 (11)	0.000 (9)	−0.007 (11)
C10	0.051 (10)	0.091 (12)	0.048 (11)	0.017 (9)	0.001 (8)	0.002 (10)
C11	0.065 (11)	0.073 (12)	0.067 (13)	0.012 (9)	0.010 (10)	0.021 (10)
C12	0.054 (10)	0.073 (11)	0.044 (11)	−0.001 (9)	0.007 (8)	0.008 (9)
C13	0.050 (9)	0.060 (10)	0.051 (12)	−0.011 (7)	−0.024 (9)	0.015 (9)
C14	0.057 (9)	0.069 (11)	0.049 (11)	−0.012 (8)	−0.013 (8)	−0.009 (10)
C15	0.038 (8)	0.038 (8)	0.077 (13)	0.004 (6)	−0.011 (9)	−0.016 (9)
C16	0.069 (10)	0.073 (10)	0.062 (12)	−0.019 (8)	−0.002 (9)	−0.008 (9)
C17	0.048 (8)	0.048 (9)	0.051 (11)	0.003 (7)	0.009 (8)	−0.004 (9)
C18	0.069 (9)	0.032 (8)	0.064 (12)	−0.001 (7)	−0.003 (9)	−0.009 (8)
C19	0.065 (9)	0.037 (9)	0.072 (13)	0.000 (7)	0.007 (9)	0.030 (9)
C20	0.027 (7)	0.040 (8)	0.056 (11)	−0.007 (6)	0.001 (7)	0.006 (8)
C21	0.063 (9)	0.064 (10)	0.037 (10)	−0.010 (8)	0.013 (8)	0.019 (9)
C22	0.090 (11)	0.101 (13)	0.048 (12)	−0.008 (9)	0.023 (9)	0.014 (10)
C23	0.074 (10)	0.070 (11)	0.057 (13)	−0.007 (9)	0.005 (9)	−0.017 (10)
C24	0.066 (10)	0.050 (10)	0.075 (14)	−0.005 (7)	0.004 (10)	−0.010 (10)
C25	0.026 (7)	0.043 (8)	0.060 (11)	−0.002 (6)	−0.008 (7)	0.013 (8)
C26	0.043 (8)	0.042 (9)	0.047 (11)	−0.005 (6)	−0.009 (7)	0.015 (8)
C27	0.035 (7)	0.026 (6)	0.045 (9)	−0.004 (5)	0.007 (7)	0.006 (6)
C28	0.027 (6)	0.041 (8)	0.028 (9)	−0.004 (6)	−0.001 (6)	−0.002 (7)
C29	0.057 (9)	0.060 (10)	0.042 (11)	−0.004 (7)	0.010 (8)	0.003 (9)
C30	0.051 (8)	0.059 (10)	0.054 (11)	−0.001 (7)	0.010 (8)	0.002 (9)
C31	0.052 (9)	0.058 (10)	0.073 (13)	0.000 (7)	0.024 (9)	−0.025 (10)
C32	0.048 (8)	0.026 (6)	0.065 (12)	0.010 (6)	0.011 (9)	0.012 (6)
C33	0.083 (10)	0.073 (10)	0.068 (13)	−0.012 (8)	0.011 (9)	0.041 (10)
F1	0.059 (5)	0.046 (4)	0.096 (7)	0.013 (4)	−0.022 (5)	0.009 (5)
F2	0.063 (5)	0.029 (4)	0.119 (8)	0.013 (3)	−0.017 (5)	−0.004 (5)
F3	0.038 (4)	0.060 (5)	0.075 (7)	0.006 (4)	−0.007 (4)	0.003 (4)
F4	0.070 (5)	0.034 (4)	0.087 (7)	−0.004 (4)	−0.008 (5)	0.008 (4)
F5	0.084 (6)	0.082 (6)	0.109 (9)	−0.032 (5)	0.016 (6)	−0.018 (6)
F6	0.051 (5)	0.196 (10)	0.105 (9)	−0.028 (6)	0.008 (6)	−0.056 (8)
F7	0.112 (7)	0.070 (6)	0.129 (10)	0.030 (6)	0.034 (6)	0.035 (6)
F8	0.052 (5)	0.067 (5)	0.113 (9)	−0.006 (4)	0.003 (5)	0.005 (5)
I1	0.0550 (6)	0.0470 (5)	0.0604 (7)	−0.0112 (4)	−0.0038 (5)	0.0009 (5)
I2	0.0506 (5)	0.0438 (5)	0.1065 (10)	−0.0087 (5)	−0.0059 (6)	−0.0008 (6)
I3	0.0577 (6)	0.0612 (6)	0.0698 (8)	0.0067 (5)	0.0091 (6)	0.0048 (6)
I4	0.0903 (9)	0.2480 (18)	0.1041 (13)	0.0790 (10)	0.0069 (9)	0.0503 (13)
N1	0.062 (7)	0.035 (7)	0.061 (10)	0.008 (5)	−0.005 (7)	0.000 (7)
N2	0.072 (8)	0.039 (7)	0.039 (9)	0.003 (6)	0.013 (7)	0.002 (6)
N3	0.048 (7)	0.042 (7)	0.075 (11)	0.006 (5)	0.002 (7)	−0.003 (7)

Geometric parameters (Å, º)

C1—C6	1.382 (14)	C18—H18	0.9300
C1—C2	1.386 (14)	C19—C20	1.430 (17)
C1—I1	2.068 (11)	C19—H19	0.9300
C2—F1	1.340 (12)	C20—C21	1.405 (18)
C2—C3	1.372 (15)	C20—C25	1.414 (16)
C3—F2	1.350 (12)	C21—C23	1.380 (18)
C3—C4	1.415 (14)	C21—C22	1.505 (16)
C4—C5	1.389 (14)	C22—H22A	0.9600
C4—I2	2.062 (11)	C22—H22B	0.9600
C5—F3	1.326 (12)	C22—H22C	0.9600
C5—C6	1.375 (15)	C23—C24	1.400 (18)
C6—F4	1.342 (11)	C23—H23	0.9300
C6—C8	3.373 (19)	C24—N2	1.296 (17)
C7—C12	1.352 (16)	C24—H24	0.9300
C7—C8	1.370 (16)	C25—N2	1.378 (15)
C7—I3	2.089 (12)	C25—C26	1.394 (17)
C8—F5	1.337 (14)	C26—N1	1.379 (14)
C8—C9	1.412 (19)	C27—N3	1.352 (13)
C9—F6	1.331 (15)	C27—C28	1.417 (14)
C9—C10	1.374 (18)	C27—C27^i	1.45 (2)
C10—C11	1.372 (17)	C28—C29	1.393 (17)
C10—I4	2.054 (13)	C28—C32	1.441 (14)
C11—F7	1.327 (15)	C29—C30	1.399 (16)
C11—C12	1.407 (17)	C29—C33	1.492 (16)
C12—F8	1.340 (13)	C30—C31	1.398 (17)
C13—N1	1.321 (17)	C30—H30	0.9300
C13—C14	1.356 (17)	C31—N3	1.324 (17)
C13—H13	0.9300	C31—H31	0.9300
C14—C15	1.395 (17)	C32—C32^i	1.32 (2)
C14—H14	0.9300	C32—H32	0.9300
C15—C17	1.358 (19)	C33—H33A	0.9600
C15—C16	1.536 (17)	C33—H33B	0.9600
C16—H16A	0.9600	C33—H33C	0.9600
C16—H16B	0.9600	I1—N2^i	3.044 (10)
C16—H16C	0.9600	I1—N1^i	3.471 (11)
C17—C18	1.405 (17)	I2—N3^ii	3.131 (10)
C17—C26	1.437 (17)	I3—N1^iii	3.025 (10)
C18—C19	1.366 (18)
C6—C1—C2	115.6 (10)	C19—C18—H18	119.6
C6—C1—I1	120.5 (9)	C17—C18—H18	119.6
C2—C1—I1	123.7 (9)	C18—C19—C20	122.7 (12)
F1—C2—C3	118.4 (11)	C18—C19—H19	118.7
F1—C2—C1	119.9 (11)	C20—C19—H19	118.7
C3—C2—C1	121.6 (11)	C21—C20—C25	120.1 (13)
F2—C3—C2	118.3 (11)	C21—C20—C19	123.7 (13)
F2—C3—C4	119.2 (10)	C25—C20—C19	116.2 (14)
C2—C3—C4	122.6 (11)	C23—C21—C20	118.2 (13)
C5—C4—C3	115.2 (10)	C23—C21—C22	121.3 (14)
C5—C4—I2	122.6 (8)	C20—C21—C22	120.4 (14)
C3—C4—I2	122.3 (8)	C21—C22—H22A	109.5
F3—C5—C6	120.5 (11)	C21—C22—H22B	109.5
F3—C5—C4	118.1 (10)	H22A—C22—H22B	109.5
C6—C5—C4	121.1 (11)	C21—C22—H22C	109.5
F4—C6—C5	116.8 (11)	H22A—C22—H22C	109.5
F4—C6—C1	119.4 (11)	H22B—C22—H22C	109.5
C5—C6—C1	123.8 (11)	C21—C23—C24	117.4 (15)
F4—C6—C8	77.2 (7)	C21—C23—H23	121.3
C5—C6—C8	84.2 (8)	C24—C23—H23	121.3
C1—C6—C8	108.5 (9)	N2—C24—C23	126.5 (14)
C12—C7—C8	116.9 (13)	N2—C24—H24	116.7
C12—C7—I3	123.7 (10)	C23—C24—H24	116.7
C8—C7—I3	119.4 (11)	N2—C25—C26	117.4 (12)
F5—C8—C7	121.1 (15)	N2—C25—C20	120.1 (14)
F5—C8—C9	117.2 (14)	C26—C25—C20	122.3 (14)
C7—C8—C9	121.4 (14)	N1—C26—C25	119.5 (13)
F5—C8—C6	89.6 (8)	N1—C26—C17	120.9 (14)
C7—C8—C6	105.3 (10)	C25—C26—C17	119.4 (13)
C9—C8—C6	79.3 (9)	N3—C27—C28	122.8 (11)
F6—C9—C10	121.5 (16)	N3—C27—C27^i	117.3 (8)
F6—C9—C8	118.0 (16)	C28—C27—C27^i	119.9 (7)
C10—C9—C8	120.3 (14)	C29—C28—C27	119.9 (11)
C11—C10—C9	118.6 (13)	C29—C28—C32	122.3 (11)
C11—C10—I4	121.5 (12)	C27—C28—C32	117.7 (11)
C9—C10—I4	119.8 (12)	C28—C29—C30	116.6 (13)
F7—C11—C10	121.3 (14)	C28—C29—C33	123.5 (13)
F7—C11—C12	119.3 (14)	C30—C29—C33	119.8 (14)
C10—C11—C12	119.3 (14)	C31—C30—C29	119.3 (14)
F8—C12—C7	120.2 (12)	C31—C30—H30	120.4
F8—C12—C11	116.4 (13)	C29—C30—H30	120.4
C7—C12—C11	123.3 (13)	N3—C31—C30	125.0 (14)
N1—C13—C14	125.1 (14)	N3—C31—H31	117.5
N1—C13—H13	117.5	C30—C31—H31	117.5
C14—C13—H13	117.5	C32^i—C32—C28	122.4 (7)
C13—C14—C15	117.8 (15)	C32^i—C32—H32	118.8
C13—C14—H14	121.1	C28—C32—H32	118.8
C15—C14—H14	121.1	C29—C33—H33A	109.5
C17—C15—C14	121.1 (13)	C29—C33—H33B	109.5
C17—C15—C16	123.0 (13)	H33A—C33—H33B	109.5
C14—C15—C16	115.7 (16)	C29—C33—H33C	109.5
C15—C16—H16A	109.5	H33A—C33—H33C	109.5
C15—C16—H16B	109.5	H33B—C33—H33C	109.5
H16A—C16—H16B	109.5	C1—I1—N2^i	162.6 (4)
C15—C16—H16C	109.5	C1—I1—N1^i	144.1 (4)
H16A—C16—H16C	109.5	N2^i—I1—N1^i	48.7 (3)
H16B—C16—H16C	109.5	C4—I2—N3^ii	164.8 (4)
C15—C17—C18	124.2 (14)	C7—I3—N1^iii	165.7 (4)
C15—C17—C26	117.2 (13)	C13—N1—C26	117.5 (12)
C18—C17—C26	118.6 (14)	C24—N2—C25	117.5 (12)
C19—C18—C17	120.8 (13)	C31—N3—C27	116.3 (12)

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

(150617a_0m)

Crystal data

C27H16F2IN2	F(000) = 1052
Mr = 533.32	Dx = 1.628 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.367 (5) Å	Cell parameters from 2530 reflections
b = 11.435 (8) Å	θ = 2.4–23.4°
c = 25.882 (16) Å	µ = 1.51 mm^−1
β = 93.609 (11)°	T = 100 K
V = 2176 (2) Å^3	Block, pale-yallow
Z = 4	0.37 × 0.33 × 0.24 mm

Data collection

Bruker APEX-II CCD diffractometer	5049 independent reflections
Radiation source: fine-focus sealed tube	3673 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.080
φ and ω scans	θmax = 27.6°, θmin = 1.6°
Absorption correction: multi-scan SADABS	h = −7→9
Tmin = 0.606, Tmax = 0.714	k = −12→14
14556 measured reflections	l = −33→30

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0493P)^2] where P = (Fo^2 + 2Fc^2)/3
5049 reflections	(Δ/σ)max = 0.001
289 parameters	Δρmax = 0.68 e Å^−3
30 restraints	Δρmin = −0.74 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
C1	0.3672 (6)	0.9335 (4)	0.47183 (18)	0.0283 (10)
C2	0.3635 (5)	0.9482 (4)	0.52444 (17)	0.0283 (10)
C3	0.4912 (6)	1.0130 (4)	0.55167 (17)	0.0291 (10)
C4	0.2892 (8)	0.7897 (8)	0.2261 (2)	0.0690 (19)
H4	0.3373	0.7133	0.2226	0.083*
C5	0.1328 (12)	0.8228 (11)	0.1964 (4)	0.103 (3)
H5	0.0732	0.7697	0.1727	0.124*
C6	0.0702 (12)	0.9292 (12)	0.2021 (4)	0.103 (3)
H6	−0.0364	0.9499	0.1816	0.124*
C7	0.1449 (11)	1.0138 (9)	0.2350 (4)	0.096 (3)
H7	0.0936	1.0897	0.2371	0.115*
C8	0.3023 (8)	0.9801 (6)	0.2651 (3)	0.0640 (18)
H8	0.3595	1.0344	0.2887	0.077*
C9	0.3753 (7)	0.8678 (5)	0.2608 (2)	0.0466 (14)
C10	0.5440 (6)	0.8360 (4)	0.29097 (19)	0.0338 (11)
C11	0.6955 (7)	0.9047 (5)	0.28818 (19)	0.0397 (12)
H11	0.6922	0.9712	0.2661	0.048*
C12	0.8551 (7)	0.8769 (5)	0.3178 (2)	0.0413 (12)
H12	0.9562	0.9280	0.3161	0.050*
C13	0.7274 (6)	0.7122 (4)	0.35050 (17)	0.0280 (9)
C14	0.5582 (5)	0.7358 (4)	0.32387 (16)	0.0277 (9)
C15	0.4074 (6)	0.6601 (4)	0.33348 (18)	0.0304 (10)
H15	0.2902	0.6778	0.3180	0.036*
C16	0.4287 (6)	0.5656 (4)	0.36376 (17)	0.0303 (10)
H16	0.3256	0.5184	0.3692	0.036*
C17	0.6001 (6)	0.5330 (4)	0.38818 (16)	0.0264 (9)
C18	0.7506 (6)	0.6086 (4)	0.38230 (16)	0.0269 (9)
C19	0.9367 (6)	0.4920 (5)	0.43367 (18)	0.0363 (11)
H19	1.0539	0.4761	0.4495	0.044*
C20	0.7985 (6)	0.4129 (4)	0.44279 (19)	0.0350 (11)
H20	0.8220	0.3465	0.4642	0.042*
C21	0.6267 (6)	0.4331 (4)	0.42005 (17)	0.0298 (10)
C22	0.4756 (6)	0.3510 (4)	0.42897 (19)	0.0311 (10)
C23	0.4226 (7)	0.3341 (4)	0.4796 (2)	0.0373 (11)
H23	0.4853	0.3736	0.5077	0.045*
C24	0.2793 (7)	0.2601 (5)	0.4888 (2)	0.0440 (13)
H24	0.2419	0.2514	0.5230	0.053*
C25	0.1919 (7)	0.2000 (5)	0.4495 (3)	0.0482 (14)
H25	0.0941	0.1494	0.4564	0.058*
C26	0.2452 (7)	0.2125 (5)	0.3990 (2)	0.0466 (13)
H26	0.1857	0.1691	0.3716	0.056*
C27	0.3867 (6)	0.2892 (5)	0.3889 (2)	0.0379 (11)
H27	0.4218	0.2990	0.3545	0.045*
F1	0.2301 (3)	0.8973 (3)	0.55017 (11)	0.0433 (7)
F2	0.4799 (4)	1.0232 (3)	0.60345 (10)	0.0443 (7)
I1	0.16711 (4)	0.83994 (3)	0.428249 (12)	0.03612 (13)
N1	0.8735 (5)	0.7847 (4)	0.34764 (14)	0.0342 (9)
N2	0.9189 (5)	0.5875 (4)	0.40486 (14)	0.0317 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.021 (2)	0.025 (2)	0.038 (3)	−0.0035 (16)	−0.0031 (18)	−0.0046 (19)
C2	0.021 (2)	0.030 (3)	0.033 (2)	−0.0059 (17)	−0.0002 (18)	−0.0011 (19)
C3	0.028 (2)	0.031 (3)	0.028 (2)	−0.0011 (18)	0.0004 (18)	−0.0027 (19)
C4	0.045 (3)	0.111 (5)	0.049 (3)	−0.024 (3)	−0.014 (3)	0.028 (4)
C5	0.076 (5)	0.155 (8)	0.077 (5)	−0.039 (5)	−0.006 (4)	0.039 (5)
C6	0.062 (4)	0.162 (8)	0.086 (5)	−0.007 (5)	0.007 (4)	0.074 (6)
C7	0.069 (4)	0.111 (6)	0.114 (6)	0.028 (4)	0.045 (4)	0.076 (5)
C8	0.046 (3)	0.078 (4)	0.070 (4)	0.015 (3)	0.020 (3)	0.045 (3)
C9	0.031 (3)	0.070 (4)	0.038 (3)	−0.004 (2)	0.000 (2)	0.031 (3)
C10	0.031 (2)	0.039 (3)	0.032 (2)	−0.0007 (19)	0.003 (2)	0.004 (2)
C11	0.037 (3)	0.048 (3)	0.034 (3)	−0.010 (2)	0.000 (2)	0.013 (2)
C12	0.033 (3)	0.048 (3)	0.043 (3)	−0.017 (2)	0.002 (2)	0.011 (2)
C13	0.026 (2)	0.032 (3)	0.026 (2)	−0.0044 (18)	0.0016 (17)	−0.0043 (19)
C14	0.022 (2)	0.035 (3)	0.025 (2)	−0.0042 (18)	−0.0017 (17)	0.0016 (19)
C15	0.022 (2)	0.036 (3)	0.032 (2)	−0.0039 (18)	−0.0024 (18)	−0.001 (2)
C16	0.022 (2)	0.037 (3)	0.032 (2)	−0.0070 (18)	0.0000 (18)	−0.001 (2)
C17	0.025 (2)	0.032 (3)	0.021 (2)	−0.0041 (17)	−0.0019 (17)	−0.0036 (18)
C18	0.024 (2)	0.036 (3)	0.021 (2)	−0.0036 (18)	−0.0001 (17)	−0.0029 (18)
C19	0.033 (2)	0.043 (3)	0.032 (2)	−0.002 (2)	−0.006 (2)	0.003 (2)
C20	0.030 (2)	0.036 (3)	0.038 (3)	0.004 (2)	−0.002 (2)	0.007 (2)
C21	0.027 (2)	0.035 (3)	0.027 (2)	−0.0026 (18)	0.0001 (18)	−0.0040 (19)
C22	0.027 (2)	0.029 (3)	0.037 (3)	−0.0001 (18)	0.0011 (19)	0.0060 (19)
C23	0.041 (3)	0.032 (3)	0.039 (3)	0.005 (2)	0.006 (2)	0.003 (2)
C24	0.040 (3)	0.036 (3)	0.058 (3)	0.006 (2)	0.019 (3)	0.007 (3)
C25	0.029 (3)	0.033 (3)	0.085 (4)	0.004 (2)	0.013 (3)	0.013 (3)
C26	0.035 (3)	0.031 (3)	0.071 (4)	−0.005 (2)	−0.014 (3)	0.000 (3)
C27	0.034 (3)	0.037 (3)	0.042 (3)	−0.005 (2)	0.000 (2)	0.001 (2)
F1	0.0291 (14)	0.058 (2)	0.0432 (16)	−0.0177 (13)	0.0081 (12)	0.0019 (14)
F2	0.0420 (16)	0.062 (2)	0.0283 (14)	−0.0132 (14)	0.0020 (12)	−0.0045 (13)
I1	0.02552 (18)	0.0423 (2)	0.0399 (2)	−0.00981 (13)	−0.00301 (13)	−0.00978 (14)
N1	0.029 (2)	0.042 (3)	0.030 (2)	−0.0113 (17)	−0.0047 (16)	0.0049 (18)
N2	0.0247 (19)	0.040 (2)	0.029 (2)	−0.0039 (16)	−0.0053 (15)	−0.0014 (17)

Geometric parameters (Å, º)

C1—C2	1.374 (6)	C13—C14	1.412 (6)
C1—C3^i	1.383 (6)	C13—C18	1.447 (7)
C1—I1	2.093 (4)	C14—C15	1.442 (6)
C1—C25^ii	3.346 (7)	C15—C16	1.339 (6)
C2—F1	1.353 (5)	C15—H15	0.9500
C2—C3	1.360 (6)	C16—C17	1.425 (6)
C3—F2	1.353 (5)	C16—H16	0.9500
C3—C1^i	1.383 (6)	C17—C21	1.416 (6)
C4—C9	1.390 (9)	C17—C18	1.421 (6)
C4—C5	1.397 (11)	C18—N2	1.358 (6)
C4—H4	0.9500	C19—N2	1.324 (6)
C5—C6	1.312 (14)	C19—C20	1.393 (7)
C5—H5	0.9500	C19—H19	0.9500
C6—C7	1.380 (14)	C20—C21	1.381 (6)
C6—C18^iii	3.329 (9)	C20—H20	0.9500
C6—H6	0.9500	C21—C22	1.485 (6)
C7—C8	1.410 (10)	C22—C27	1.385 (7)
C7—C13^iii	3.345 (8)	C22—C23	1.404 (7)
C7—C18^iii	3.357 (9)	C23—C24	1.385 (7)
C7—H7	0.9500	C23—H23	0.9500
C8—C9	1.400 (9)	C24—C25	1.355 (8)
C8—H8	0.9500	C24—H24	0.9500
C9—C10	1.471 (7)	C25—C26	1.396 (8)
C10—C11	1.371 (7)	C25—H25	0.9500
C10—C14	1.427 (6)	C26—C27	1.400 (7)
C11—C12	1.399 (7)	C26—H26	0.9500
C11—H11	0.9500	C27—H27	0.9500
C12—N1	1.310 (6)	I1—N1^iv	2.977 (4)
C12—H12	0.9500	I1—N2^iv	3.451 (4)
C13—N1	1.364 (6)
C2—C1—C3^i	116.4 (4)	N1—C13—C18	117.6 (4)
C2—C1—I1	122.6 (3)	C14—C13—C18	120.2 (4)
C3^i—C1—I1	120.9 (3)	C13—C14—C10	118.3 (4)
C2—C1—C25^ii	91.6 (3)	C13—C14—C15	117.8 (4)
C3^i—C1—C25^ii	79.4 (3)	C10—C14—C15	123.8 (4)
I1—C1—C25^ii	96.98 (19)	C16—C15—C14	121.5 (4)
F1—C2—C3	118.7 (4)	C16—C15—H15	119.3
F1—C2—C1	119.7 (4)	C14—C15—H15	119.3
C3—C2—C1	121.6 (4)	C15—C16—C17	122.6 (4)
F2—C3—C2	118.5 (4)	C15—C16—H16	118.7
F2—C3—C1^i	119.5 (4)	C17—C16—H16	118.7
C2—C3—C1^i	122.0 (4)	C21—C17—C18	118.2 (4)
C9—C4—C5	120.6 (9)	C21—C17—C16	123.7 (4)
C9—C4—H4	119.7	C18—C17—C16	118.0 (4)
C5—C4—H4	119.7	N2—C18—C17	122.9 (4)
C6—C5—C4	118.2 (10)	N2—C18—C13	117.5 (4)
C6—C5—H5	120.9	C17—C18—C13	119.6 (4)
C4—C5—H5	120.9	N2—C19—C20	125.7 (4)
C5—C6—C7	126.1 (9)	N2—C19—H19	117.2
C5—C6—C18^iii	110.0 (6)	C20—C19—H19	117.2
C7—C6—C18^iii	79.3 (5)	C21—C20—C19	118.6 (5)
C5—C6—H6	116.9	C21—C20—H20	120.7
C7—C6—H6	116.9	C19—C20—H20	120.7
C18^iii—C6—H6	80.1	C20—C21—C17	118.2 (4)
C6—C7—C8	115.6 (9)	C20—C21—C22	120.3 (4)
C6—C7—C13^iii	100.7 (5)	C17—C21—C22	121.6 (4)
C8—C7—C13^iii	107.2 (5)	C27—C22—C23	118.8 (4)
C6—C7—C18^iii	76.9 (5)	C27—C22—C21	122.0 (4)
C8—C7—C18^iii	111.2 (4)	C23—C22—C21	119.2 (4)
C13^iii—C7—C18^iii	24.93 (12)	C24—C23—C22	120.2 (5)
C6—C7—H7	122.2	C24—C23—H23	119.9
C8—C7—H7	122.2	C22—C23—H23	119.9
C13^iii—C7—H7	63.2	C25—C24—C23	120.8 (5)
C18^iii—C7—H7	82.7	C25—C24—H24	119.6
C9—C8—C7	120.9 (8)	C23—C24—H24	119.6
C9—C8—H8	119.6	C24—C25—C26	120.1 (5)
C7—C8—H8	119.6	C24—C25—H25	119.9
C4—C9—C8	118.6 (6)	C26—C25—H25	119.9
C4—C9—C10	121.3 (6)	C25—C26—C27	119.7 (5)
C8—C9—C10	120.0 (6)	C25—C26—H26	120.2
C11—C10—C14	117.5 (4)	C27—C26—H26	120.2
C11—C10—C9	119.6 (5)	C22—C27—C26	120.2 (5)
C14—C10—C9	122.9 (4)	C22—C27—H27	119.9
C10—C11—C12	120.0 (5)	C26—C27—H27	119.9
C10—C11—H11	120.0	C1—I1—N1^iv	160.42 (15)
C12—C11—H11	120.0	C1—I1—N2^iv	150.44 (14)
N1—C12—C11	123.9 (4)	N1^iv—I1—N2^iv	49.14 (10)
N1—C12—H12	118.0	C12—N1—C13	118.0 (4)
C11—C12—H12	118.0	C19—N2—C18	116.4 (4)
N1—C13—C14	122.2 (4)

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

(1)

Crystal data

C15H6Cl2F2IN2	F(000) = 860
Mr = 450.02	Dx = 1.981 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.5713 (10) Å	Cell parameters from 4288 reflections
b = 21.091 (2) Å	θ = 2.3–27.5°
c = 7.1214 (7) Å	µ = 2.49 mm^−1
β = 108.149 (2)°	T = 296 K
V = 1508.8 (3) Å^3	Block, pale-yellow
Z = 4

Data collection

Bruker APEX-II CCD diffractometer	3404 independent reflections
Radiation source: fine-focus sealed tube	2899 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 27.6°, θmin = 1.9°
Absorption correction: multi-scan	h = −13→12
Tmin = 0.530, Tmax = 0.746	k = −27→11
8418 measured reflections	l = −9→9

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) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0435P)^2 + 0.6889P] where P = (Fo^2 + 2Fc^2)/3
3404 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.85 e Å^−3
0 restraints	Δρmin = −1.11 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
I1	0.27436 (2)	0.398258 (11)	0.16527 (3)	0.05797 (11)
Cl1	0.52755 (13)	0.05800 (4)	0.33875 (19)	0.0847 (3)
Cl2	1.00409 (9)	0.32697 (6)	0.72108 (19)	0.0875 (3)
F1	0.0283 (2)	0.42786 (13)	0.3243 (4)	0.0872 (8)
F2	−0.1796 (2)	0.50480 (13)	0.1982 (4)	0.0871 (8)
N2	0.5753 (3)	0.35926 (12)	0.3659 (4)	0.0500 (6)
N1	0.4044 (2)	0.26266 (13)	0.2260 (4)	0.0497 (6)
C7	0.5306 (3)	0.24772 (13)	0.3336 (4)	0.0392 (6)
C8	0.6219 (3)	0.29911 (13)	0.4076 (4)	0.0390 (6)
C12	0.7560 (3)	0.28519 (14)	0.5181 (4)	0.0416 (6)
C1	0.1113 (3)	0.45930 (13)	0.0667 (4)	0.0445 (6)
C15	0.5765 (3)	0.18467 (13)	0.3742 (4)	0.0425 (6)
C2	0.0157 (3)	0.46304 (15)	0.1622 (5)	0.0500 (7)
C14	0.7117 (3)	0.17305 (14)	0.4867 (5)	0.0497 (7)
H14	0.7412	0.1315	0.5132	0.060*
C3	−0.0921 (3)	0.50290 (16)	0.0971 (5)	0.0517 (7)
C4	0.4814 (4)	0.13679 (15)	0.2981 (5)	0.0537 (8)
C13	0.7974 (3)	0.22100 (15)	0.5552 (5)	0.0494 (7)
H13	0.8852	0.2121	0.6279	0.059*
C11	0.8394 (3)	0.33799 (17)	0.5827 (5)	0.0548 (8)
C5	0.3537 (4)	0.15177 (18)	0.1925 (5)	0.0625 (9)
H5	0.2904	0.1203	0.1437	0.075*
C6	0.3208 (3)	0.21569 (19)	0.1598 (5)	0.0615 (9)
H6	0.2338	0.2258	0.0862	0.074*
C10	0.7919 (4)	0.39821 (16)	0.5393 (7)	0.0673 (10)
H10	0.8472	0.4331	0.5816	0.081*
C9	0.6589 (4)	0.40598 (16)	0.4305 (7)	0.0651 (10)
H9	0.6271	0.4471	0.4017	0.078*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.05144 (15)	0.06538 (16)	0.05562 (16)	0.02333 (10)	0.01457 (10)	0.01240 (9)
Cl1	0.1152 (9)	0.0422 (4)	0.1032 (8)	−0.0110 (5)	0.0434 (7)	−0.0013 (5)
Cl2	0.0445 (5)	0.1049 (8)	0.1011 (8)	−0.0127 (5)	0.0053 (5)	−0.0073 (6)
F1	0.0820 (15)	0.1092 (18)	0.0842 (16)	0.0418 (14)	0.0458 (13)	0.0562 (14)
F2	0.0714 (13)	0.117 (2)	0.0922 (17)	0.0434 (14)	0.0535 (13)	0.0493 (15)
N2	0.0526 (14)	0.0411 (13)	0.0588 (16)	0.0062 (11)	0.0207 (12)	0.0052 (11)
N1	0.0391 (13)	0.0586 (15)	0.0500 (15)	0.0028 (11)	0.0119 (11)	0.0055 (12)
C7	0.0433 (14)	0.0446 (14)	0.0346 (13)	0.0014 (11)	0.0192 (11)	0.0030 (11)
C8	0.0419 (14)	0.0424 (14)	0.0371 (14)	0.0040 (11)	0.0186 (11)	0.0044 (11)
C12	0.0407 (14)	0.0486 (15)	0.0390 (14)	0.0021 (12)	0.0176 (12)	0.0008 (11)
C1	0.0397 (14)	0.0410 (14)	0.0490 (16)	0.0052 (11)	0.0082 (12)	0.0024 (12)
C15	0.0528 (16)	0.0422 (14)	0.0375 (14)	0.0003 (12)	0.0213 (12)	0.0032 (11)
C2	0.0499 (16)	0.0484 (16)	0.0509 (17)	0.0093 (13)	0.0148 (13)	0.0148 (13)
C14	0.0589 (18)	0.0423 (15)	0.0498 (17)	0.0120 (13)	0.0197 (14)	0.0076 (13)
C3	0.0454 (16)	0.0579 (18)	0.0564 (19)	0.0103 (14)	0.0225 (14)	0.0098 (15)
C4	0.074 (2)	0.0450 (16)	0.0494 (17)	−0.0113 (15)	0.0300 (16)	−0.0010 (13)
C13	0.0437 (15)	0.0584 (18)	0.0463 (16)	0.0118 (13)	0.0146 (13)	0.0070 (14)
C11	0.0447 (16)	0.068 (2)	0.0539 (18)	−0.0069 (15)	0.0185 (14)	−0.0043 (15)
C5	0.066 (2)	0.068 (2)	0.0533 (19)	−0.0257 (18)	0.0184 (16)	−0.0069 (16)
C6	0.0460 (17)	0.082 (2)	0.054 (2)	−0.0102 (17)	0.0110 (14)	0.0054 (17)
C10	0.070 (2)	0.054 (2)	0.080 (3)	−0.0181 (17)	0.026 (2)	−0.0073 (17)
C9	0.073 (2)	0.0436 (17)	0.081 (3)	0.0011 (16)	0.027 (2)	0.0026 (16)

Geometric parameters (Å, º)

I1—C1	2.090 (3)	C1—C2	1.384 (4)
I1—N1	3.144 (3)	C15—C4	1.409 (4)
I1—N2	3.163 (3)	C15—C14	1.426 (4)
Cl1—C4	1.731 (4)	C2—C3	1.375 (4)
Cl2—C11	1.728 (3)	C14—C13	1.344 (5)
F1—C2	1.343 (4)	C14—H14	0.9300
F2—C3	1.339 (4)	C3—C1^i	1.375 (4)
N2—C9	1.308 (4)	C4—C5	1.362 (5)
N2—C8	1.360 (3)	C13—H13	0.9300
N1—C6	1.314 (4)	C11—C10	1.365 (5)
N1—C7	1.352 (4)	C5—C6	1.394 (6)
C7—C15	1.414 (4)	C5—H5	0.9300
C7—C8	1.438 (4)	C6—H6	0.9300
C8—C12	1.421 (4)	C10—C9	1.388 (6)
C12—C11	1.406 (4)	C10—H10	0.9300
C12—C13	1.422 (4)	C9—H9	0.9300
C1—C3^i	1.375 (4)
C1—I1—N1	152.39 (9)	C13—C14—C15	121.3 (3)
C1—I1—N2	156.94 (9)	C13—C14—H14	119.4
N1—I1—N2	50.67 (6)	C15—C14—H14	119.4
C9—N2—C8	117.8 (3)	F2—C3—C1^i	119.7 (3)
C9—N2—I1	115.9 (2)	F2—C3—C2	118.4 (3)
C8—N2—I1	125.91 (19)	C1^i—C3—C2	121.9 (3)
C6—N1—C7	117.6 (3)	C5—C4—C15	120.8 (3)
C6—N1—I1	114.8 (2)	C5—C4—Cl1	119.6 (3)
C7—N1—I1	126.99 (19)	C15—C4—Cl1	119.6 (3)
N1—C7—C15	123.4 (3)	C14—C13—C12	121.0 (3)
N1—C7—C8	117.6 (2)	C14—C13—H13	119.5
C15—C7—C8	119.0 (3)	C12—C13—H13	119.5
N2—C8—C12	123.0 (3)	C10—C11—C12	120.9 (3)
N2—C8—C7	117.8 (2)	C10—C11—Cl2	119.2 (3)
C12—C8—C7	119.2 (2)	C12—C11—Cl2	119.9 (3)
C11—C12—C8	115.7 (3)	C4—C5—C6	118.0 (3)
C11—C12—C13	124.6 (3)	C4—C5—H5	121.0
C8—C12—C13	119.7 (3)	C6—C5—H5	121.0
C3^i—C1—C2	116.5 (3)	N1—C6—C5	124.4 (3)
C3^i—C1—I1	122.0 (2)	N1—C6—H6	117.8
C2—C1—I1	121.5 (2)	C5—C6—H6	117.8
C4—C15—C7	115.9 (3)	C11—C10—C9	118.3 (3)
C4—C15—C14	124.3 (3)	C11—C10—H10	120.9
C7—C15—C14	119.8 (3)	C9—C10—H10	120.9
F1—C2—C3	118.5 (3)	N2—C9—C10	124.3 (3)
F1—C2—C1	119.9 (3)	N2—C9—H9	117.9
C3—C2—C1	121.6 (3)	C10—C9—H9	117.8
C1—I1—N2—C9	−2.0 (4)	C3^i—C1—C2—F1	−179.5 (3)
N1—I1—N2—C9	178.7 (3)	I1—C1—C2—F1	1.4 (4)
C1—I1—N2—C8	171.1 (3)	C3^i—C1—C2—C3	−0.5 (5)
N1—I1—N2—C8	−8.2 (2)	I1—C1—C2—C3	−179.6 (3)
C1—I1—N1—C6	−0.1 (3)	C4—C15—C14—C13	−179.9 (3)
N2—I1—N1—C6	179.3 (3)	C7—C15—C14—C13	−0.2 (5)
C1—I1—N1—C7	−170.8 (2)	F1—C2—C3—F2	0.0 (5)
N2—I1—N1—C7	8.6 (2)	C1—C2—C3—F2	−179.0 (3)
C6—N1—C7—C15	1.2 (4)	F1—C2—C3—C1^i	179.5 (3)
I1—N1—C7—C15	171.65 (19)	C1—C2—C3—C1^i	0.6 (6)
C6—N1—C7—C8	−179.5 (3)	C7—C15—C4—C5	0.0 (4)
I1—N1—C7—C8	−9.1 (4)	C14—C15—C4—C5	179.7 (3)
C9—N2—C8—C12	0.4 (5)	C7—C15—C4—Cl1	179.8 (2)
I1—N2—C8—C12	−172.58 (19)	C14—C15—C4—Cl1	−0.5 (4)
C9—N2—C8—C7	−179.0 (3)	C15—C14—C13—C12	0.1 (5)
I1—N2—C8—C7	8.1 (4)	C11—C12—C13—C14	−179.4 (3)
N1—C7—C8—N2	0.5 (4)	C8—C12—C13—C14	0.2 (5)
C15—C7—C8—N2	179.8 (3)	C8—C12—C11—C10	−0.1 (5)
N1—C7—C8—C12	−178.8 (3)	C13—C12—C11—C10	179.5 (3)
C15—C7—C8—C12	0.5 (4)	C8—C12—C11—Cl2	179.2 (2)
N2—C8—C12—C11	−0.2 (4)	C13—C12—C11—Cl2	−1.2 (4)
C7—C8—C12—C11	179.1 (3)	C15—C4—C5—C6	0.9 (5)
N2—C8—C12—C13	−179.8 (3)	Cl1—C4—C5—C6	−178.9 (3)
C7—C8—C12—C13	−0.5 (4)	C7—N1—C6—C5	−0.2 (5)
N1—I1—C1—C3^i	−107.3 (3)	I1—N1—C6—C5	−171.8 (3)
N2—I1—C1—C3^i	73.9 (4)	C4—C5—C6—N1	−0.8 (6)
N1—I1—C1—C2	71.8 (3)	C12—C11—C10—C9	0.3 (6)
N2—I1—C1—C2	−107.0 (3)	Cl2—C11—C10—C9	−179.1 (3)
N1—C7—C15—C4	−1.1 (4)	C8—N2—C9—C10	−0.2 (6)
C8—C7—C15—C4	179.6 (3)	I1—N2—C9—C10	173.4 (3)
N1—C7—C15—C14	179.2 (3)	C11—C10—C9—N2	−0.1 (7)
C8—C7—C15—C14	−0.1 (4)

Symmetry code: (i) −x, −y+1, −z.