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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S205252061700292X/ao5026sup1.cif
Contains datablocks 160411a_0m, 150617a_0m, 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252061700292X/ao5026160411a_0msup2.hkl
Contains datablock 160411a_0m

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252061700292X/ao5026150617a_0msup3.hkl
Contains datablock 150617a_0m

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252061700292X/ao50261sup4.hkl
Contains datablock 1

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S205252061700292X/ao5026sup5.pdf
Supporting figures

CCDC references: 1518205; 1518206; 1518207

Computing details top

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) top
Crystal data top
C33H18F8I4N3F(000) = 4168
Mr = 1116.10Dx = 2.145 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 11.455 (4) ÅCell parameters from 656 reflections
b = 27.777 (10) Åθ = 2.6–17.9°
c = 21.823 (9) ŵ = 3.68 mm1
β = 95.607 (9)°T = 296 K
V = 6911 (4) Å3Block, pale-yellow
Z = 80.17 × 0.11 × 0.10 mm
Data collection top
Bruker APEX-II CCD
diffractometer
7926 independent reflections
Radiation source: fine-focus sealed tube2398 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.165
φ and ω scansθmax = 27.5°, θmin = 1.5°
Absorption correction: multi-scan
SADABS
h = 1414
Tmin = 0.574, Tmax = 0.710k = 3236
22301 measured reflectionsl = 1928
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149H atoms treated by a mixture of independent and constrained refinement
S = 0.87 w = 1/[σ2(Fo2) + (0.030P)2]
where P = (Fo2 + 2Fc2)/3
7926 reflections(Δ/σ)max < 0.001
435 parametersΔρmax = 1.10 e Å3
0 restraintsΔρmin = 1.42 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
C10.4925 (9)0.1804 (4)0.3335 (6)0.037 (3)
C20.5114 (11)0.1311 (5)0.3330 (6)0.048 (4)
C30.4230 (11)0.0994 (4)0.3144 (7)0.060 (4)
C40.3093 (9)0.1148 (4)0.2915 (6)0.040 (3)
C50.2935 (10)0.1643 (4)0.2888 (6)0.045 (4)
C60.3817 (11)0.1953 (4)0.3106 (6)0.046 (4)
C70.1114 (11)0.1905 (5)0.4106 (7)0.051 (4)
C80.2185 (14)0.2102 (5)0.4297 (7)0.065 (5)
C90.3112 (13)0.1818 (7)0.4577 (7)0.074 (5)
C100.2988 (12)0.1327 (6)0.4620 (7)0.063 (4)
C110.1924 (13)0.1126 (6)0.4422 (7)0.068 (5)
C120.1017 (12)0.1421 (5)0.4153 (7)0.057 (4)
C130.1562 (11)0.3085 (5)0.2524 (7)0.056 (4)
H130.14590.27840.26970.067*
C140.1473 (10)0.3475 (5)0.2888 (7)0.059 (4)
H140.13170.34420.32970.071*
C150.1624 (10)0.3928 (5)0.2632 (8)0.052 (4)
C160.1455 (10)0.4359 (5)0.3055 (7)0.068 (4)
H16A0.13200.42450.34570.103*
H16B0.07920.45460.28880.103*
H16C0.21460.45570.30840.103*
C170.1831 (10)0.3977 (5)0.2033 (8)0.048 (4)
C180.1948 (11)0.4422 (4)0.1739 (7)0.055 (4)
H180.18550.47060.19540.066*
C190.2196 (10)0.4443 (5)0.1140 (7)0.058 (4)
H190.22490.47420.09550.070*
C200.2378 (9)0.4021 (4)0.0785 (7)0.041 (3)
C210.2655 (11)0.4033 (5)0.0172 (7)0.054 (4)
C220.2724 (11)0.4506 (5)0.0160 (7)0.078 (5)
H22A0.28160.44470.05860.118*
H22B0.33840.46870.00220.118*
H22C0.20170.46860.01270.118*
C230.2810 (11)0.3601 (6)0.0122 (7)0.067 (5)
H230.29810.35910.05300.081*
C240.2699 (11)0.3179 (5)0.0218 (8)0.064 (5)
H240.28090.28900.00160.077*
C250.2243 (9)0.3575 (5)0.1081 (7)0.044 (4)
C260.1976 (10)0.3543 (5)0.1690 (7)0.045 (4)
C270.4879 (9)0.4450 (4)0.2820 (5)0.035 (3)
C280.4739 (9)0.4008 (4)0.3128 (6)0.033 (3)
C290.4500 (10)0.4007 (5)0.3742 (7)0.053 (4)
C300.4391 (10)0.4458 (5)0.4018 (7)0.054 (4)
H300.42000.44800.44210.065*
C310.4574 (10)0.4874 (5)0.3680 (8)0.060 (4)
H310.45590.51680.38850.072*
C320.4870 (10)0.3570 (4)0.2787 (6)0.046 (4)
H320.47670.32770.29800.055*
C330.4295 (11)0.3560 (4)0.4094 (7)0.074 (5)
H33A0.35610.34190.39380.111*
H33B0.42740.36380.45220.111*
H33C0.49180.33360.40510.111*
F10.6160 (6)0.1132 (2)0.3547 (4)0.069 (3)
F20.4469 (6)0.0519 (2)0.3174 (4)0.072 (3)
F30.1877 (5)0.1811 (2)0.2698 (4)0.059 (2)
F40.3568 (6)0.2425 (2)0.3082 (4)0.065 (2)
F50.2361 (6)0.2577 (3)0.4273 (4)0.091 (3)
F60.4123 (7)0.2036 (4)0.4757 (5)0.117 (4)
F70.1749 (7)0.0655 (3)0.4453 (5)0.102 (3)
F80.0003 (6)0.1202 (2)0.3965 (4)0.078 (3)
I10.62177 (7)0.23024 (3)0.35990 (5)0.0548 (3)
I20.17799 (7)0.06692 (3)0.26217 (6)0.0679 (4)
I30.02562 (7)0.23528 (3)0.37571 (5)0.0627 (3)
I40.43465 (11)0.09201 (6)0.50263 (7)0.1477 (7)
N10.1783 (9)0.3098 (4)0.1941 (6)0.053 (3)
N20.2458 (9)0.3151 (4)0.0784 (6)0.050 (3)
N30.4767 (9)0.4883 (4)0.3092 (6)0.055 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.037 (7)0.043 (8)0.034 (9)0.001 (6)0.013 (7)0.008 (6)
C20.054 (9)0.049 (9)0.038 (10)0.010 (7)0.009 (8)0.002 (7)
C30.064 (9)0.025 (8)0.088 (14)0.010 (7)0.005 (9)0.001 (8)
C40.039 (7)0.031 (7)0.049 (10)0.005 (6)0.001 (7)0.001 (7)
C50.038 (8)0.047 (9)0.050 (10)0.007 (7)0.002 (7)0.003 (7)
C60.071 (10)0.022 (7)0.046 (10)0.006 (7)0.013 (8)0.002 (7)
C70.046 (8)0.050 (9)0.057 (11)0.001 (7)0.006 (8)0.004 (8)
C80.074 (11)0.061 (11)0.064 (13)0.019 (9)0.026 (10)0.006 (9)
C90.049 (10)0.119 (16)0.052 (13)0.009 (11)0.000 (9)0.007 (11)
C100.051 (10)0.091 (12)0.048 (11)0.017 (9)0.001 (8)0.002 (10)
C110.065 (11)0.073 (12)0.067 (13)0.012 (9)0.010 (10)0.021 (10)
C120.054 (10)0.073 (11)0.044 (11)0.001 (9)0.007 (8)0.008 (9)
C130.050 (9)0.060 (10)0.051 (12)0.011 (7)0.024 (9)0.015 (9)
C140.057 (9)0.069 (11)0.049 (11)0.012 (8)0.013 (8)0.009 (10)
C150.038 (8)0.038 (8)0.077 (13)0.004 (6)0.011 (9)0.016 (9)
C160.069 (10)0.073 (10)0.062 (12)0.019 (8)0.002 (9)0.008 (9)
C170.048 (8)0.048 (9)0.051 (11)0.003 (7)0.009 (8)0.004 (9)
C180.069 (9)0.032 (8)0.064 (12)0.001 (7)0.003 (9)0.009 (8)
C190.065 (9)0.037 (9)0.072 (13)0.000 (7)0.007 (9)0.030 (9)
C200.027 (7)0.040 (8)0.056 (11)0.007 (6)0.001 (7)0.006 (8)
C210.063 (9)0.064 (10)0.037 (10)0.010 (8)0.013 (8)0.019 (9)
C220.090 (11)0.101 (13)0.048 (12)0.008 (9)0.023 (9)0.014 (10)
C230.074 (10)0.070 (11)0.057 (13)0.007 (9)0.005 (9)0.017 (10)
C240.066 (10)0.050 (10)0.075 (14)0.005 (7)0.004 (10)0.010 (10)
C250.026 (7)0.043 (8)0.060 (11)0.002 (6)0.008 (7)0.013 (8)
C260.043 (8)0.042 (9)0.047 (11)0.005 (6)0.009 (7)0.015 (8)
C270.035 (7)0.026 (6)0.045 (9)0.004 (5)0.007 (7)0.006 (6)
C280.027 (6)0.041 (8)0.028 (9)0.004 (6)0.001 (6)0.002 (7)
C290.057 (9)0.060 (10)0.042 (11)0.004 (7)0.010 (8)0.003 (9)
C300.051 (8)0.059 (10)0.054 (11)0.001 (7)0.010 (8)0.002 (9)
C310.052 (9)0.058 (10)0.073 (13)0.000 (7)0.024 (9)0.025 (10)
C320.048 (8)0.026 (6)0.065 (12)0.010 (6)0.011 (9)0.012 (6)
C330.083 (10)0.073 (10)0.068 (13)0.012 (8)0.011 (9)0.041 (10)
F10.059 (5)0.046 (4)0.096 (7)0.013 (4)0.022 (5)0.009 (5)
F20.063 (5)0.029 (4)0.119 (8)0.013 (3)0.017 (5)0.004 (5)
F30.038 (4)0.060 (5)0.075 (7)0.006 (4)0.007 (4)0.003 (4)
F40.070 (5)0.034 (4)0.087 (7)0.004 (4)0.008 (5)0.008 (4)
F50.084 (6)0.082 (6)0.109 (9)0.032 (5)0.016 (6)0.018 (6)
F60.051 (5)0.196 (10)0.105 (9)0.028 (6)0.008 (6)0.056 (8)
F70.112 (7)0.070 (6)0.129 (10)0.030 (6)0.034 (6)0.035 (6)
F80.052 (5)0.067 (5)0.113 (9)0.006 (4)0.003 (5)0.005 (5)
I10.0550 (6)0.0470 (5)0.0604 (7)0.0112 (4)0.0038 (5)0.0009 (5)
I20.0506 (5)0.0438 (5)0.1065 (10)0.0087 (5)0.0059 (6)0.0008 (6)
I30.0577 (6)0.0612 (6)0.0698 (8)0.0067 (5)0.0091 (6)0.0048 (6)
I40.0903 (9)0.2480 (18)0.1041 (13)0.0790 (10)0.0069 (9)0.0503 (13)
N10.062 (7)0.035 (7)0.061 (10)0.008 (5)0.005 (7)0.000 (7)
N20.072 (8)0.039 (7)0.039 (9)0.003 (6)0.013 (7)0.002 (6)
N30.048 (7)0.042 (7)0.075 (11)0.006 (5)0.002 (7)0.003 (7)
Geometric parameters (Å, º) top
C1—C61.382 (14)C18—H180.9300
C1—C21.386 (14)C19—C201.430 (17)
C1—I12.068 (11)C19—H190.9300
C2—F11.340 (12)C20—C211.405 (18)
C2—C31.372 (15)C20—C251.414 (16)
C3—F21.350 (12)C21—C231.380 (18)
C3—C41.415 (14)C21—C221.505 (16)
C4—C51.389 (14)C22—H22A0.9600
C4—I22.062 (11)C22—H22B0.9600
C5—F31.326 (12)C22—H22C0.9600
C5—C61.375 (15)C23—C241.400 (18)
C6—F41.342 (11)C23—H230.9300
C6—C83.373 (19)C24—N21.296 (17)
C7—C121.352 (16)C24—H240.9300
C7—C81.370 (16)C25—N21.378 (15)
C7—I32.089 (12)C25—C261.394 (17)
C8—F51.337 (14)C26—N11.379 (14)
C8—C91.412 (19)C27—N31.352 (13)
C9—F61.331 (15)C27—C281.417 (14)
C9—C101.374 (18)C27—C27i1.45 (2)
C10—C111.372 (17)C28—C291.393 (17)
C10—I42.054 (13)C28—C321.441 (14)
C11—F71.327 (15)C29—C301.399 (16)
C11—C121.407 (17)C29—C331.492 (16)
C12—F81.340 (13)C30—C311.398 (17)
C13—N11.321 (17)C30—H300.9300
C13—C141.356 (17)C31—N31.324 (17)
C13—H130.9300C31—H310.9300
C14—C151.395 (17)C32—C32i1.32 (2)
C14—H140.9300C32—H320.9300
C15—C171.358 (19)C33—H33A0.9600
C15—C161.536 (17)C33—H33B0.9600
C16—H16A0.9600C33—H33C0.9600
C16—H16B0.9600I1—N2i3.044 (10)
C16—H16C0.9600I1—N1i3.471 (11)
C17—C181.405 (17)I2—N3ii3.131 (10)
C17—C261.437 (17)I3—N1iii3.025 (10)
C18—C191.366 (18)
C6—C1—C2115.6 (10)C19—C18—H18119.6
C6—C1—I1120.5 (9)C17—C18—H18119.6
C2—C1—I1123.7 (9)C18—C19—C20122.7 (12)
F1—C2—C3118.4 (11)C18—C19—H19118.7
F1—C2—C1119.9 (11)C20—C19—H19118.7
C3—C2—C1121.6 (11)C21—C20—C25120.1 (13)
F2—C3—C2118.3 (11)C21—C20—C19123.7 (13)
F2—C3—C4119.2 (10)C25—C20—C19116.2 (14)
C2—C3—C4122.6 (11)C23—C21—C20118.2 (13)
C5—C4—C3115.2 (10)C23—C21—C22121.3 (14)
C5—C4—I2122.6 (8)C20—C21—C22120.4 (14)
C3—C4—I2122.3 (8)C21—C22—H22A109.5
F3—C5—C6120.5 (11)C21—C22—H22B109.5
F3—C5—C4118.1 (10)H22A—C22—H22B109.5
C6—C5—C4121.1 (11)C21—C22—H22C109.5
F4—C6—C5116.8 (11)H22A—C22—H22C109.5
F4—C6—C1119.4 (11)H22B—C22—H22C109.5
C5—C6—C1123.8 (11)C21—C23—C24117.4 (15)
F4—C6—C877.2 (7)C21—C23—H23121.3
C5—C6—C884.2 (8)C24—C23—H23121.3
C1—C6—C8108.5 (9)N2—C24—C23126.5 (14)
C12—C7—C8116.9 (13)N2—C24—H24116.7
C12—C7—I3123.7 (10)C23—C24—H24116.7
C8—C7—I3119.4 (11)N2—C25—C26117.4 (12)
F5—C8—C7121.1 (15)N2—C25—C20120.1 (14)
F5—C8—C9117.2 (14)C26—C25—C20122.3 (14)
C7—C8—C9121.4 (14)N1—C26—C25119.5 (13)
F5—C8—C689.6 (8)N1—C26—C17120.9 (14)
C7—C8—C6105.3 (10)C25—C26—C17119.4 (13)
C9—C8—C679.3 (9)N3—C27—C28122.8 (11)
F6—C9—C10121.5 (16)N3—C27—C27i117.3 (8)
F6—C9—C8118.0 (16)C28—C27—C27i119.9 (7)
C10—C9—C8120.3 (14)C29—C28—C27119.9 (11)
C11—C10—C9118.6 (13)C29—C28—C32122.3 (11)
C11—C10—I4121.5 (12)C27—C28—C32117.7 (11)
C9—C10—I4119.8 (12)C28—C29—C30116.6 (13)
F7—C11—C10121.3 (14)C28—C29—C33123.5 (13)
F7—C11—C12119.3 (14)C30—C29—C33119.8 (14)
C10—C11—C12119.3 (14)C31—C30—C29119.3 (14)
F8—C12—C7120.2 (12)C31—C30—H30120.4
F8—C12—C11116.4 (13)C29—C30—H30120.4
C7—C12—C11123.3 (13)N3—C31—C30125.0 (14)
N1—C13—C14125.1 (14)N3—C31—H31117.5
N1—C13—H13117.5C30—C31—H31117.5
C14—C13—H13117.5C32i—C32—C28122.4 (7)
C13—C14—C15117.8 (15)C32i—C32—H32118.8
C13—C14—H14121.1C28—C32—H32118.8
C15—C14—H14121.1C29—C33—H33A109.5
C17—C15—C14121.1 (13)C29—C33—H33B109.5
C17—C15—C16123.0 (13)H33A—C33—H33B109.5
C14—C15—C16115.7 (16)C29—C33—H33C109.5
C15—C16—H16A109.5H33A—C33—H33C109.5
C15—C16—H16B109.5H33B—C33—H33C109.5
H16A—C16—H16B109.5C1—I1—N2i162.6 (4)
C15—C16—H16C109.5C1—I1—N1i144.1 (4)
H16A—C16—H16C109.5N2i—I1—N1i48.7 (3)
H16B—C16—H16C109.5C4—I2—N3ii164.8 (4)
C15—C17—C18124.2 (14)C7—I3—N1iii165.7 (4)
C15—C17—C26117.2 (13)C13—N1—C26117.5 (12)
C18—C17—C26118.6 (14)C24—N2—C25117.5 (12)
C19—C18—C17120.8 (13)C31—N3—C27116.3 (12)
Symmetry codes: (i) x+1, y, z+1/2; (ii) x+1/2, y1/2, z+1/2; (iii) x, y, z+1/2.
(150617a_0m) top
Crystal data top
C27H16F2IN2F(000) = 1052
Mr = 533.32Dx = 1.628 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 7.367 (5) ÅCell parameters from 2530 reflections
b = 11.435 (8) Åθ = 2.4–23.4°
c = 25.882 (16) ŵ = 1.51 mm1
β = 93.609 (11)°T = 100 K
V = 2176 (2) Å3Block, pale-yallow
Z = 40.37 × 0.33 × 0.24 mm
Data collection top
Bruker APEX-II CCD
diffractometer
5049 independent reflections
Radiation source: fine-focus sealed tube3673 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.080
φ and ω scansθmax = 27.6°, θmin = 1.6°
Absorption correction: multi-scan
SADABS
h = 79
Tmin = 0.606, Tmax = 0.714k = 1214
14556 measured reflectionsl = 3330
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H atoms treated by a mixture of independent and constrained refinement
S = 0.99 w = 1/[σ2(Fo2) + (0.0493P)2]
where P = (Fo2 + 2Fc2)/3
5049 reflections(Δ/σ)max = 0.001
289 parametersΔρmax = 0.68 e Å3
30 restraintsΔρmin = 0.74 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
C10.3672 (6)0.9335 (4)0.47183 (18)0.0283 (10)
C20.3635 (5)0.9482 (4)0.52444 (17)0.0283 (10)
C30.4912 (6)1.0130 (4)0.55167 (17)0.0291 (10)
C40.2892 (8)0.7897 (8)0.2261 (2)0.0690 (19)
H40.33730.71330.22260.083*
C50.1328 (12)0.8228 (11)0.1964 (4)0.103 (3)
H50.07320.76970.17270.124*
C60.0702 (12)0.9292 (12)0.2021 (4)0.103 (3)
H60.03640.94990.18160.124*
C70.1449 (11)1.0138 (9)0.2350 (4)0.096 (3)
H70.09361.08970.23710.115*
C80.3023 (8)0.9801 (6)0.2651 (3)0.0640 (18)
H80.35951.03440.28870.077*
C90.3753 (7)0.8678 (5)0.2608 (2)0.0466 (14)
C100.5440 (6)0.8360 (4)0.29097 (19)0.0338 (11)
C110.6955 (7)0.9047 (5)0.28818 (19)0.0397 (12)
H110.69220.97120.26610.048*
C120.8551 (7)0.8769 (5)0.3178 (2)0.0413 (12)
H120.95620.92800.31610.050*
C130.7274 (6)0.7122 (4)0.35050 (17)0.0280 (9)
C140.5582 (5)0.7358 (4)0.32387 (16)0.0277 (9)
C150.4074 (6)0.6601 (4)0.33348 (18)0.0304 (10)
H150.29020.67780.31800.036*
C160.4287 (6)0.5656 (4)0.36376 (17)0.0303 (10)
H160.32560.51840.36920.036*
C170.6001 (6)0.5330 (4)0.38818 (16)0.0264 (9)
C180.7506 (6)0.6086 (4)0.38230 (16)0.0269 (9)
C190.9367 (6)0.4920 (5)0.43367 (18)0.0363 (11)
H191.05390.47610.44950.044*
C200.7985 (6)0.4129 (4)0.44279 (19)0.0350 (11)
H200.82200.34650.46420.042*
C210.6267 (6)0.4331 (4)0.42005 (17)0.0298 (10)
C220.4756 (6)0.3510 (4)0.42897 (19)0.0311 (10)
C230.4226 (7)0.3341 (4)0.4796 (2)0.0373 (11)
H230.48530.37360.50770.045*
C240.2793 (7)0.2601 (5)0.4888 (2)0.0440 (13)
H240.24190.25140.52300.053*
C250.1919 (7)0.2000 (5)0.4495 (3)0.0482 (14)
H250.09410.14940.45640.058*
C260.2452 (7)0.2125 (5)0.3990 (2)0.0466 (13)
H260.18570.16910.37160.056*
C270.3867 (6)0.2892 (5)0.3889 (2)0.0379 (11)
H270.42180.29900.35450.045*
F10.2301 (3)0.8973 (3)0.55017 (11)0.0433 (7)
F20.4799 (4)1.0232 (3)0.60345 (10)0.0443 (7)
I10.16711 (4)0.83994 (3)0.428249 (12)0.03612 (13)
N10.8735 (5)0.7847 (4)0.34764 (14)0.0342 (9)
N20.9189 (5)0.5875 (4)0.40486 (14)0.0317 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.021 (2)0.025 (2)0.038 (3)0.0035 (16)0.0031 (18)0.0046 (19)
C20.021 (2)0.030 (3)0.033 (2)0.0059 (17)0.0002 (18)0.0011 (19)
C30.028 (2)0.031 (3)0.028 (2)0.0011 (18)0.0004 (18)0.0027 (19)
C40.045 (3)0.111 (5)0.049 (3)0.024 (3)0.014 (3)0.028 (4)
C50.076 (5)0.155 (8)0.077 (5)0.039 (5)0.006 (4)0.039 (5)
C60.062 (4)0.162 (8)0.086 (5)0.007 (5)0.007 (4)0.074 (6)
C70.069 (4)0.111 (6)0.114 (6)0.028 (4)0.045 (4)0.076 (5)
C80.046 (3)0.078 (4)0.070 (4)0.015 (3)0.020 (3)0.045 (3)
C90.031 (3)0.070 (4)0.038 (3)0.004 (2)0.000 (2)0.031 (3)
C100.031 (2)0.039 (3)0.032 (2)0.0007 (19)0.003 (2)0.004 (2)
C110.037 (3)0.048 (3)0.034 (3)0.010 (2)0.000 (2)0.013 (2)
C120.033 (3)0.048 (3)0.043 (3)0.017 (2)0.002 (2)0.011 (2)
C130.026 (2)0.032 (3)0.026 (2)0.0044 (18)0.0016 (17)0.0043 (19)
C140.022 (2)0.035 (3)0.025 (2)0.0042 (18)0.0017 (17)0.0016 (19)
C150.022 (2)0.036 (3)0.032 (2)0.0039 (18)0.0024 (18)0.001 (2)
C160.022 (2)0.037 (3)0.032 (2)0.0070 (18)0.0000 (18)0.001 (2)
C170.025 (2)0.032 (3)0.021 (2)0.0041 (17)0.0019 (17)0.0036 (18)
C180.024 (2)0.036 (3)0.021 (2)0.0036 (18)0.0001 (17)0.0029 (18)
C190.033 (2)0.043 (3)0.032 (2)0.002 (2)0.006 (2)0.003 (2)
C200.030 (2)0.036 (3)0.038 (3)0.004 (2)0.002 (2)0.007 (2)
C210.027 (2)0.035 (3)0.027 (2)0.0026 (18)0.0001 (18)0.0040 (19)
C220.027 (2)0.029 (3)0.037 (3)0.0001 (18)0.0011 (19)0.0060 (19)
C230.041 (3)0.032 (3)0.039 (3)0.005 (2)0.006 (2)0.003 (2)
C240.040 (3)0.036 (3)0.058 (3)0.006 (2)0.019 (3)0.007 (3)
C250.029 (3)0.033 (3)0.085 (4)0.004 (2)0.013 (3)0.013 (3)
C260.035 (3)0.031 (3)0.071 (4)0.005 (2)0.014 (3)0.000 (3)
C270.034 (3)0.037 (3)0.042 (3)0.005 (2)0.000 (2)0.001 (2)
F10.0291 (14)0.058 (2)0.0432 (16)0.0177 (13)0.0081 (12)0.0019 (14)
F20.0420 (16)0.062 (2)0.0283 (14)0.0132 (14)0.0020 (12)0.0045 (13)
I10.02552 (18)0.0423 (2)0.0399 (2)0.00981 (13)0.00301 (13)0.00978 (14)
N10.029 (2)0.042 (3)0.030 (2)0.0113 (17)0.0047 (16)0.0049 (18)
N20.0247 (19)0.040 (2)0.029 (2)0.0039 (16)0.0053 (15)0.0014 (17)
Geometric parameters (Å, º) top
C1—C21.374 (6)C13—C141.412 (6)
C1—C3i1.383 (6)C13—C181.447 (7)
C1—I12.093 (4)C14—C151.442 (6)
C1—C25ii3.346 (7)C15—C161.339 (6)
C2—F11.353 (5)C15—H150.9500
C2—C31.360 (6)C16—C171.425 (6)
C3—F21.353 (5)C16—H160.9500
C3—C1i1.383 (6)C17—C211.416 (6)
C4—C91.390 (9)C17—C181.421 (6)
C4—C51.397 (11)C18—N21.358 (6)
C4—H40.9500C19—N21.324 (6)
C5—C61.312 (14)C19—C201.393 (7)
C5—H50.9500C19—H190.9500
C6—C71.380 (14)C20—C211.381 (6)
C6—C18iii3.329 (9)C20—H200.9500
C6—H60.9500C21—C221.485 (6)
C7—C81.410 (10)C22—C271.385 (7)
C7—C13iii3.345 (8)C22—C231.404 (7)
C7—C18iii3.357 (9)C23—C241.385 (7)
C7—H70.9500C23—H230.9500
C8—C91.400 (9)C24—C251.355 (8)
C8—H80.9500C24—H240.9500
C9—C101.471 (7)C25—C261.396 (8)
C10—C111.371 (7)C25—H250.9500
C10—C141.427 (6)C26—C271.400 (7)
C11—C121.399 (7)C26—H260.9500
C11—H110.9500C27—H270.9500
C12—N11.310 (6)I1—N1iv2.977 (4)
C12—H120.9500I1—N2iv3.451 (4)
C13—N11.364 (6)
C2—C1—C3i116.4 (4)N1—C13—C18117.6 (4)
C2—C1—I1122.6 (3)C14—C13—C18120.2 (4)
C3i—C1—I1120.9 (3)C13—C14—C10118.3 (4)
C2—C1—C25ii91.6 (3)C13—C14—C15117.8 (4)
C3i—C1—C25ii79.4 (3)C10—C14—C15123.8 (4)
I1—C1—C25ii96.98 (19)C16—C15—C14121.5 (4)
F1—C2—C3118.7 (4)C16—C15—H15119.3
F1—C2—C1119.7 (4)C14—C15—H15119.3
C3—C2—C1121.6 (4)C15—C16—C17122.6 (4)
F2—C3—C2118.5 (4)C15—C16—H16118.7
F2—C3—C1i119.5 (4)C17—C16—H16118.7
C2—C3—C1i122.0 (4)C21—C17—C18118.2 (4)
C9—C4—C5120.6 (9)C21—C17—C16123.7 (4)
C9—C4—H4119.7C18—C17—C16118.0 (4)
C5—C4—H4119.7N2—C18—C17122.9 (4)
C6—C5—C4118.2 (10)N2—C18—C13117.5 (4)
C6—C5—H5120.9C17—C18—C13119.6 (4)
C4—C5—H5120.9N2—C19—C20125.7 (4)
C5—C6—C7126.1 (9)N2—C19—H19117.2
C5—C6—C18iii110.0 (6)C20—C19—H19117.2
C7—C6—C18iii79.3 (5)C21—C20—C19118.6 (5)
C5—C6—H6116.9C21—C20—H20120.7
C7—C6—H6116.9C19—C20—H20120.7
C18iii—C6—H680.1C20—C21—C17118.2 (4)
C6—C7—C8115.6 (9)C20—C21—C22120.3 (4)
C6—C7—C13iii100.7 (5)C17—C21—C22121.6 (4)
C8—C7—C13iii107.2 (5)C27—C22—C23118.8 (4)
C6—C7—C18iii76.9 (5)C27—C22—C21122.0 (4)
C8—C7—C18iii111.2 (4)C23—C22—C21119.2 (4)
C13iii—C7—C18iii24.93 (12)C24—C23—C22120.2 (5)
C6—C7—H7122.2C24—C23—H23119.9
C8—C7—H7122.2C22—C23—H23119.9
C13iii—C7—H763.2C25—C24—C23120.8 (5)
C18iii—C7—H782.7C25—C24—H24119.6
C9—C8—C7120.9 (8)C23—C24—H24119.6
C9—C8—H8119.6C24—C25—C26120.1 (5)
C7—C8—H8119.6C24—C25—H25119.9
C4—C9—C8118.6 (6)C26—C25—H25119.9
C4—C9—C10121.3 (6)C25—C26—C27119.7 (5)
C8—C9—C10120.0 (6)C25—C26—H26120.2
C11—C10—C14117.5 (4)C27—C26—H26120.2
C11—C10—C9119.6 (5)C22—C27—C26120.2 (5)
C14—C10—C9122.9 (4)C22—C27—H27119.9
C10—C11—C12120.0 (5)C26—C27—H27119.9
C10—C11—H11120.0C1—I1—N1iv160.42 (15)
C12—C11—H11120.0C1—I1—N2iv150.44 (14)
N1—C12—C11123.9 (4)N1iv—I1—N2iv49.14 (10)
N1—C12—H12118.0C12—N1—C13118.0 (4)
C11—C12—H12118.0C19—N2—C18116.4 (4)
N1—C13—C14122.2 (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) x1, y, z.
(1) top
Crystal data top
C15H6Cl2F2IN2F(000) = 860
Mr = 450.02Dx = 1.981 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.5713 (10) ÅCell parameters from 4288 reflections
b = 21.091 (2) Åθ = 2.3–27.5°
c = 7.1214 (7) ŵ = 2.49 mm1
β = 108.149 (2)°T = 296 K
V = 1508.8 (3) Å3Block, pale-yellow
Z = 4
Data collection top
Bruker APEX-II CCD
diffractometer
3404 independent reflections
Radiation source: fine-focus sealed tube2899 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
φ and ω scansθmax = 27.6°, θmin = 1.9°
Absorption correction: multi-scanh = 1312
Tmin = 0.530, Tmax = 0.746k = 2711
8418 measured reflectionsl = 99
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0435P)2 + 0.6889P]
where P = (Fo2 + 2Fc2)/3
3404 reflections(Δ/σ)max < 0.001
199 parametersΔρmax = 0.85 e Å3
0 restraintsΔρmin = 1.11 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
I10.27436 (2)0.398258 (11)0.16527 (3)0.05797 (11)
Cl10.52755 (13)0.05800 (4)0.33875 (19)0.0847 (3)
Cl21.00409 (9)0.32697 (6)0.72108 (19)0.0875 (3)
F10.0283 (2)0.42786 (13)0.3243 (4)0.0872 (8)
F20.1796 (2)0.50480 (13)0.1982 (4)0.0871 (8)
N20.5753 (3)0.35926 (12)0.3659 (4)0.0500 (6)
N10.4044 (2)0.26266 (13)0.2260 (4)0.0497 (6)
C70.5306 (3)0.24772 (13)0.3336 (4)0.0392 (6)
C80.6219 (3)0.29911 (13)0.4076 (4)0.0390 (6)
C120.7560 (3)0.28519 (14)0.5181 (4)0.0416 (6)
C10.1113 (3)0.45930 (13)0.0667 (4)0.0445 (6)
C150.5765 (3)0.18467 (13)0.3742 (4)0.0425 (6)
C20.0157 (3)0.46304 (15)0.1622 (5)0.0500 (7)
C140.7117 (3)0.17305 (14)0.4867 (5)0.0497 (7)
H140.74120.13150.51320.060*
C30.0921 (3)0.50290 (16)0.0971 (5)0.0517 (7)
C40.4814 (4)0.13679 (15)0.2981 (5)0.0537 (8)
C130.7974 (3)0.22100 (15)0.5552 (5)0.0494 (7)
H130.88520.21210.62790.059*
C110.8394 (3)0.33799 (17)0.5827 (5)0.0548 (8)
C50.3537 (4)0.15177 (18)0.1925 (5)0.0625 (9)
H50.29040.12030.14370.075*
C60.3208 (3)0.21569 (19)0.1598 (5)0.0615 (9)
H60.23380.22580.08620.074*
C100.7919 (4)0.39821 (16)0.5393 (7)0.0673 (10)
H100.84720.43310.58160.081*
C90.6589 (4)0.40598 (16)0.4305 (7)0.0651 (10)
H90.62710.44710.40170.078*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.05144 (15)0.06538 (16)0.05562 (16)0.02333 (10)0.01457 (10)0.01240 (9)
Cl10.1152 (9)0.0422 (4)0.1032 (8)0.0110 (5)0.0434 (7)0.0013 (5)
Cl20.0445 (5)0.1049 (8)0.1011 (8)0.0127 (5)0.0053 (5)0.0073 (6)
F10.0820 (15)0.1092 (18)0.0842 (16)0.0418 (14)0.0458 (13)0.0562 (14)
F20.0714 (13)0.117 (2)0.0922 (17)0.0434 (14)0.0535 (13)0.0493 (15)
N20.0526 (14)0.0411 (13)0.0588 (16)0.0062 (11)0.0207 (12)0.0052 (11)
N10.0391 (13)0.0586 (15)0.0500 (15)0.0028 (11)0.0119 (11)0.0055 (12)
C70.0433 (14)0.0446 (14)0.0346 (13)0.0014 (11)0.0192 (11)0.0030 (11)
C80.0419 (14)0.0424 (14)0.0371 (14)0.0040 (11)0.0186 (11)0.0044 (11)
C120.0407 (14)0.0486 (15)0.0390 (14)0.0021 (12)0.0176 (12)0.0008 (11)
C10.0397 (14)0.0410 (14)0.0490 (16)0.0052 (11)0.0082 (12)0.0024 (12)
C150.0528 (16)0.0422 (14)0.0375 (14)0.0003 (12)0.0213 (12)0.0032 (11)
C20.0499 (16)0.0484 (16)0.0509 (17)0.0093 (13)0.0148 (13)0.0148 (13)
C140.0589 (18)0.0423 (15)0.0498 (17)0.0120 (13)0.0197 (14)0.0076 (13)
C30.0454 (16)0.0579 (18)0.0564 (19)0.0103 (14)0.0225 (14)0.0098 (15)
C40.074 (2)0.0450 (16)0.0494 (17)0.0113 (15)0.0300 (16)0.0010 (13)
C130.0437 (15)0.0584 (18)0.0463 (16)0.0118 (13)0.0146 (13)0.0070 (14)
C110.0447 (16)0.068 (2)0.0539 (18)0.0069 (15)0.0185 (14)0.0043 (15)
C50.066 (2)0.068 (2)0.0533 (19)0.0257 (18)0.0184 (16)0.0069 (16)
C60.0460 (17)0.082 (2)0.054 (2)0.0102 (17)0.0110 (14)0.0054 (17)
C100.070 (2)0.054 (2)0.080 (3)0.0181 (17)0.026 (2)0.0073 (17)
C90.073 (2)0.0436 (17)0.081 (3)0.0011 (16)0.027 (2)0.0026 (16)
Geometric parameters (Å, º) top
I1—C12.090 (3)C1—C21.384 (4)
I1—N13.144 (3)C15—C41.409 (4)
I1—N23.163 (3)C15—C141.426 (4)
Cl1—C41.731 (4)C2—C31.375 (4)
Cl2—C111.728 (3)C14—C131.344 (5)
F1—C21.343 (4)C14—H140.9300
F2—C31.339 (4)C3—C1i1.375 (4)
N2—C91.308 (4)C4—C51.362 (5)
N2—C81.360 (3)C13—H130.9300
N1—C61.314 (4)C11—C101.365 (5)
N1—C71.352 (4)C5—C61.394 (6)
C7—C151.414 (4)C5—H50.9300
C7—C81.438 (4)C6—H60.9300
C8—C121.421 (4)C10—C91.388 (6)
C12—C111.406 (4)C10—H100.9300
C12—C131.422 (4)C9—H90.9300
C1—C3i1.375 (4)
C1—I1—N1152.39 (9)C13—C14—C15121.3 (3)
C1—I1—N2156.94 (9)C13—C14—H14119.4
N1—I1—N250.67 (6)C15—C14—H14119.4
C9—N2—C8117.8 (3)F2—C3—C1i119.7 (3)
C9—N2—I1115.9 (2)F2—C3—C2118.4 (3)
C8—N2—I1125.91 (19)C1i—C3—C2121.9 (3)
C6—N1—C7117.6 (3)C5—C4—C15120.8 (3)
C6—N1—I1114.8 (2)C5—C4—Cl1119.6 (3)
C7—N1—I1126.99 (19)C15—C4—Cl1119.6 (3)
N1—C7—C15123.4 (3)C14—C13—C12121.0 (3)
N1—C7—C8117.6 (2)C14—C13—H13119.5
C15—C7—C8119.0 (3)C12—C13—H13119.5
N2—C8—C12123.0 (3)C10—C11—C12120.9 (3)
N2—C8—C7117.8 (2)C10—C11—Cl2119.2 (3)
C12—C8—C7119.2 (2)C12—C11—Cl2119.9 (3)
C11—C12—C8115.7 (3)C4—C5—C6118.0 (3)
C11—C12—C13124.6 (3)C4—C5—H5121.0
C8—C12—C13119.7 (3)C6—C5—H5121.0
C3i—C1—C2116.5 (3)N1—C6—C5124.4 (3)
C3i—C1—I1122.0 (2)N1—C6—H6117.8
C2—C1—I1121.5 (2)C5—C6—H6117.8
C4—C15—C7115.9 (3)C11—C10—C9118.3 (3)
C4—C15—C14124.3 (3)C11—C10—H10120.9
C7—C15—C14119.8 (3)C9—C10—H10120.9
F1—C2—C3118.5 (3)N2—C9—C10124.3 (3)
F1—C2—C1119.9 (3)N2—C9—H9117.9
C3—C2—C1121.6 (3)C10—C9—H9117.8
C1—I1—N2—C92.0 (4)C3i—C1—C2—F1179.5 (3)
N1—I1—N2—C9178.7 (3)I1—C1—C2—F11.4 (4)
C1—I1—N2—C8171.1 (3)C3i—C1—C2—C30.5 (5)
N1—I1—N2—C88.2 (2)I1—C1—C2—C3179.6 (3)
C1—I1—N1—C60.1 (3)C4—C15—C14—C13179.9 (3)
N2—I1—N1—C6179.3 (3)C7—C15—C14—C130.2 (5)
C1—I1—N1—C7170.8 (2)F1—C2—C3—F20.0 (5)
N2—I1—N1—C78.6 (2)C1—C2—C3—F2179.0 (3)
C6—N1—C7—C151.2 (4)F1—C2—C3—C1i179.5 (3)
I1—N1—C7—C15171.65 (19)C1—C2—C3—C1i0.6 (6)
C6—N1—C7—C8179.5 (3)C7—C15—C4—C50.0 (4)
I1—N1—C7—C89.1 (4)C14—C15—C4—C5179.7 (3)
C9—N2—C8—C120.4 (5)C7—C15—C4—Cl1179.8 (2)
I1—N2—C8—C12172.58 (19)C14—C15—C4—Cl10.5 (4)
C9—N2—C8—C7179.0 (3)C15—C14—C13—C120.1 (5)
I1—N2—C8—C78.1 (4)C11—C12—C13—C14179.4 (3)
N1—C7—C8—N20.5 (4)C8—C12—C13—C140.2 (5)
C15—C7—C8—N2179.8 (3)C8—C12—C11—C100.1 (5)
N1—C7—C8—C12178.8 (3)C13—C12—C11—C10179.5 (3)
C15—C7—C8—C120.5 (4)C8—C12—C11—Cl2179.2 (2)
N2—C8—C12—C110.2 (4)C13—C12—C11—Cl21.2 (4)
C7—C8—C12—C11179.1 (3)C15—C4—C5—C60.9 (5)
N2—C8—C12—C13179.8 (3)Cl1—C4—C5—C6178.9 (3)
C7—C8—C12—C130.5 (4)C7—N1—C6—C50.2 (5)
N1—I1—C1—C3i107.3 (3)I1—N1—C6—C5171.8 (3)
N2—I1—C1—C3i73.9 (4)C4—C5—C6—N10.8 (6)
N1—I1—C1—C271.8 (3)C12—C11—C10—C90.3 (6)
N2—I1—C1—C2107.0 (3)Cl2—C11—C10—C9179.1 (3)
N1—C7—C15—C41.1 (4)C8—N2—C9—C100.2 (6)
C8—C7—C15—C4179.6 (3)I1—N2—C9—C10173.4 (3)
N1—C7—C15—C14179.2 (3)C11—C10—C9—N20.1 (7)
C8—C7—C15—C140.1 (4)
Symmetry code: (i) x, y+1, z.
 

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