Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520617003444/bm5091sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520617003444/bm5091ico231sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520617003444/bm5091ico281_4sup3.hkl | |
Zip compressed file https://doi.org/10.1107/S2052520617003444/bm5091sup4.zip |
CCDC references: 1449803; 1449806
For both compounds, data collection: Bruker APEX2; cell refinement: Bruker SAINT; data reduction: Bruker SAINT; program(s) used to solve structure: SHELXS (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122). Program(s) used to refine structure: SHELXL97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122) for ico231; SHELXL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122) for ico281_4. For both compounds, molecular graphics: ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457. Software used to prepare material for publication: SHELXL97 for ico231; SHELXL for ico281_4.
C24H29F4IN2O | Z = 2 |
Mr = 564.39 | F(000) = 568 |
Triclinic, P1 | Dx = 1.587 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.4374 (9) Å | Cell parameters from 9935 reflections |
b = 10.2935 (12) Å | θ = 2.6–34.9° |
c = 16.536 (2) Å | µ = 1.41 mm−1 |
α = 105.237 (10)° | T = 103 K |
β = 101.641 (10)° | Flat Prism, orange |
γ = 95.607 (12)° | 0.40 × 0.25 × 0.05 mm |
V = 1181.0 (2) Å3 |
Bruker APEX-II CCD diffractometer | 10045 independent reflections |
Radiation source: fine-focus sealed tube | 8800 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
φ and ω scans | θmax = 35.7°, θmin = 2.1° |
Absorption correction: multi-scan Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. | h = −12→12 |
Tmin = 0.553, Tmax = 0.706 | k = −16→16 |
39236 measured reflections | l = −26→26 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.080 | H-atom parameters not refined |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0425P)2 + 0.3826P] where P = (Fo2 + 2Fc2)/3 |
10045 reflections | (Δ/σ)max = 0.001 |
290 parameters | Δρmax = 1.39 e Å−3 |
0 restraints | Δρmin = −1.72 e Å−3 |
Experimental. Bruker KRYOFLEX low temperature device. |
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. |
x | y | z | Uiso*/Ueq | ||
I1 | −1.032228 (12) | 0.233555 (10) | −0.130000 (6) | 0.02364 (3) | |
F1 | −0.38325 (13) | 0.06570 (9) | −0.04237 (6) | 0.02267 (17) | |
F2 | −0.72409 (13) | 0.03719 (9) | −0.13340 (6) | 0.02432 (18) | |
F3 | −0.78666 (13) | 0.47590 (9) | 0.02874 (6) | 0.02363 (18) | |
F4 | −0.44186 (13) | 0.50605 (9) | 0.12306 (6) | 0.02269 (17) | |
O1 | 0.59484 (15) | 0.36006 (11) | 0.29865 (7) | 0.0229 (2) | |
N1 | −0.21713 (17) | 0.32153 (13) | 0.09942 (8) | 0.0194 (2) | |
N2 | −0.11712 (17) | 0.22878 (13) | 0.08737 (8) | 0.0200 (2) | |
C1 | −0.47714 (19) | 0.16927 (14) | −0.02183 (9) | 0.0174 (2) | |
C2 | −0.6567 (2) | 0.15381 (14) | −0.07001 (9) | 0.0187 (2) | |
C3 | −0.76610 (19) | 0.25559 (15) | −0.05494 (9) | 0.0185 (2) | |
C4 | −0.6888 (2) | 0.37353 (14) | 0.01176 (9) | 0.0183 (2) | |
C5 | −0.50994 (19) | 0.38927 (14) | 0.06028 (9) | 0.0176 (2) | |
C6 | −0.39736 (19) | 0.28853 (14) | 0.04520 (9) | 0.0168 (2) | |
C7 | 0.06324 (19) | 0.26716 (14) | 0.14248 (9) | 0.0174 (2) | |
C8 | 0.1734 (2) | 0.16420 (15) | 0.13852 (10) | 0.0200 (2) | |
H8 | 0.1252 | 0.0757 | 0.1000 | 0.024* | |
C9 | 0.3531 (2) | 0.18983 (15) | 0.19033 (9) | 0.0192 (2) | |
H9 | 0.4270 | 0.1193 | 0.1882 | 0.023* | |
C10 | 0.4229 (2) | 0.32103 (14) | 0.24541 (9) | 0.0185 (2) | |
C11 | 0.3134 (2) | 0.42484 (15) | 0.24785 (10) | 0.0214 (3) | |
H11 | 0.3629 | 0.5142 | 0.2848 | 0.026* | |
C12 | 0.1352 (2) | 0.39889 (15) | 0.19741 (9) | 0.0203 (2) | |
H12 | 0.0615 | 0.4696 | 0.1998 | 0.024* | |
C13 | 0.7167 (2) | 0.26024 (15) | 0.30047 (9) | 0.0196 (2) | |
H13A | 0.7363 | 0.2203 | 0.2421 | 0.023* | |
H13B | 0.6624 | 0.1859 | 0.3202 | 0.023* | |
C14 | 0.8984 (2) | 0.33278 (15) | 0.36217 (10) | 0.0202 (2) | |
H14A | 0.8747 | 0.3772 | 0.4190 | 0.024* | |
H14B | 0.9519 | 0.4051 | 0.3405 | 0.024* | |
C15 | 1.03874 (19) | 0.23712 (15) | 0.37353 (10) | 0.0199 (2) | |
H15A | 0.9854 | 0.1651 | 0.3955 | 0.024* | |
H15B | 1.0617 | 0.1923 | 0.3166 | 0.024* | |
C16 | 1.22276 (19) | 0.30984 (15) | 0.43527 (10) | 0.0199 (2) | |
H16A | 1.1983 | 0.3587 | 0.4911 | 0.024* | |
H16B | 1.2783 | 0.3789 | 0.4117 | 0.024* | |
C17 | 1.3630 (2) | 0.21589 (15) | 0.45142 (10) | 0.0207 (3) | |
H17A | 1.3862 | 0.1657 | 0.3956 | 0.025* | |
H17B | 1.3091 | 0.1481 | 0.4763 | 0.025* | |
C18 | 1.5474 (2) | 0.29147 (15) | 0.51204 (10) | 0.0213 (3) | |
H18A | 1.5233 | 0.3451 | 0.5669 | 0.026* | |
H18B | 1.6037 | 0.3564 | 0.4859 | 0.026* | |
C19 | 1.6860 (2) | 0.19764 (15) | 0.53182 (10) | 0.0214 (3) | |
H19A | 1.6290 | 0.1326 | 0.5577 | 0.026* | |
H19B | 1.7095 | 0.1440 | 0.4769 | 0.026* | |
C20 | 1.8718 (2) | 0.27090 (15) | 0.59251 (10) | 0.0206 (3) | |
H20A | 1.9311 | 0.3350 | 0.5666 | 0.025* | |
H20B | 1.8497 | 0.3249 | 0.6477 | 0.025* | |
C21 | 2.0034 (2) | 0.17184 (15) | 0.61045 (10) | 0.0222 (3) | |
H21A | 2.0183 | 0.1146 | 0.5546 | 0.027* | |
H21B | 1.9449 | 0.1107 | 0.6384 | 0.027* | |
C22 | 2.1960 (2) | 0.23800 (15) | 0.66732 (10) | 0.0200 (2) | |
H22A | 2.2586 | 0.2963 | 0.6389 | 0.024* | |
H22B | 2.1831 | 0.2969 | 0.7231 | 0.024* | |
C23 | 2.3148 (2) | 0.13084 (16) | 0.68374 (11) | 0.0244 (3) | |
H23A | 2.2495 | 0.0720 | 0.7110 | 0.029* | |
H23B | 2.3263 | 0.0725 | 0.6275 | 0.029* | |
C24 | 2.5089 (2) | 0.18819 (17) | 0.74072 (11) | 0.0266 (3) | |
H24A | 2.5781 | 0.2418 | 0.7127 | 0.040* | |
H24B | 2.5741 | 0.1130 | 0.7497 | 0.040* | |
H24C | 2.4997 | 0.2467 | 0.7965 | 0.040* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.01525 (5) | 0.02909 (6) | 0.02601 (5) | 0.00334 (3) | 0.00098 (3) | 0.01008 (4) |
F1 | 0.0194 (4) | 0.0195 (4) | 0.0257 (4) | 0.0069 (3) | 0.0037 (3) | 0.0007 (3) |
F2 | 0.0218 (4) | 0.0201 (4) | 0.0237 (4) | 0.0008 (3) | −0.0002 (3) | −0.0011 (3) |
F3 | 0.0217 (4) | 0.0216 (4) | 0.0289 (5) | 0.0098 (3) | 0.0061 (4) | 0.0071 (4) |
F4 | 0.0242 (4) | 0.0170 (4) | 0.0224 (4) | 0.0029 (3) | 0.0028 (3) | 0.0002 (3) |
O1 | 0.0180 (5) | 0.0201 (5) | 0.0245 (5) | 0.0046 (4) | −0.0033 (4) | 0.0021 (4) |
N1 | 0.0161 (5) | 0.0216 (5) | 0.0192 (5) | 0.0037 (4) | 0.0024 (4) | 0.0046 (4) |
N2 | 0.0161 (5) | 0.0206 (5) | 0.0222 (6) | 0.0036 (4) | 0.0016 (4) | 0.0063 (4) |
C1 | 0.0164 (5) | 0.0167 (5) | 0.0190 (6) | 0.0044 (4) | 0.0046 (4) | 0.0042 (5) |
C2 | 0.0170 (6) | 0.0188 (6) | 0.0178 (6) | 0.0007 (4) | 0.0024 (5) | 0.0028 (5) |
C3 | 0.0148 (5) | 0.0213 (6) | 0.0202 (6) | 0.0035 (4) | 0.0033 (4) | 0.0079 (5) |
C4 | 0.0168 (6) | 0.0183 (5) | 0.0210 (6) | 0.0047 (4) | 0.0051 (5) | 0.0067 (5) |
C5 | 0.0183 (6) | 0.0163 (5) | 0.0170 (6) | 0.0024 (4) | 0.0038 (4) | 0.0034 (4) |
C6 | 0.0152 (5) | 0.0185 (5) | 0.0169 (5) | 0.0034 (4) | 0.0034 (4) | 0.0054 (5) |
C7 | 0.0150 (5) | 0.0188 (6) | 0.0172 (6) | 0.0028 (4) | 0.0019 (4) | 0.0048 (5) |
C8 | 0.0179 (6) | 0.0180 (6) | 0.0214 (6) | 0.0034 (4) | 0.0013 (5) | 0.0032 (5) |
C9 | 0.0174 (6) | 0.0185 (6) | 0.0198 (6) | 0.0046 (4) | 0.0016 (5) | 0.0038 (5) |
C10 | 0.0171 (6) | 0.0193 (6) | 0.0172 (6) | 0.0037 (4) | 0.0015 (4) | 0.0040 (5) |
C11 | 0.0204 (6) | 0.0186 (6) | 0.0205 (6) | 0.0046 (5) | −0.0005 (5) | 0.0014 (5) |
C12 | 0.0197 (6) | 0.0198 (6) | 0.0196 (6) | 0.0059 (5) | 0.0019 (5) | 0.0037 (5) |
C13 | 0.0155 (6) | 0.0206 (6) | 0.0204 (6) | 0.0042 (4) | 0.0006 (5) | 0.0047 (5) |
C14 | 0.0155 (6) | 0.0216 (6) | 0.0214 (6) | 0.0025 (4) | 0.0012 (5) | 0.0050 (5) |
C15 | 0.0125 (5) | 0.0231 (6) | 0.0209 (6) | 0.0031 (4) | −0.0006 (4) | 0.0045 (5) |
C16 | 0.0148 (5) | 0.0213 (6) | 0.0221 (6) | 0.0024 (4) | 0.0027 (5) | 0.0051 (5) |
C17 | 0.0145 (5) | 0.0223 (6) | 0.0214 (6) | 0.0014 (4) | 0.0006 (5) | 0.0031 (5) |
C18 | 0.0136 (5) | 0.0231 (6) | 0.0228 (6) | 0.0010 (4) | 0.0009 (5) | 0.0023 (5) |
C19 | 0.0154 (6) | 0.0217 (6) | 0.0223 (6) | 0.0022 (4) | 0.0001 (5) | 0.0020 (5) |
C20 | 0.0149 (6) | 0.0217 (6) | 0.0220 (6) | 0.0019 (4) | 0.0017 (5) | 0.0032 (5) |
C21 | 0.0173 (6) | 0.0211 (6) | 0.0228 (6) | 0.0023 (5) | −0.0014 (5) | 0.0021 (5) |
C22 | 0.0157 (6) | 0.0212 (6) | 0.0201 (6) | 0.0013 (4) | 0.0013 (5) | 0.0039 (5) |
C23 | 0.0188 (6) | 0.0229 (6) | 0.0260 (7) | 0.0031 (5) | −0.0031 (5) | 0.0044 (6) |
C24 | 0.0195 (7) | 0.0276 (7) | 0.0287 (8) | 0.0033 (5) | −0.0014 (6) | 0.0069 (6) |
I1—C3 | 2.0694 (14) | C14—H14B | 0.9900 |
F1—C1 | 1.3380 (15) | C15—C16 | 1.520 (2) |
F2—C2 | 1.3416 (16) | C15—H15A | 0.9900 |
F3—C4 | 1.3398 (16) | C15—H15B | 0.9900 |
F4—C5 | 1.3387 (16) | C16—C17 | 1.522 (2) |
O1—C10 | 1.3533 (18) | C16—H16A | 0.9900 |
O1—C13 | 1.4373 (18) | C16—H16B | 0.9900 |
N1—N2 | 1.2661 (17) | C17—C18 | 1.522 (2) |
N1—C6 | 1.4078 (19) | C17—H17A | 0.9900 |
N2—C7 | 1.4141 (18) | C17—H17B | 0.9900 |
C1—C2 | 1.381 (2) | C18—C19 | 1.526 (2) |
C1—C6 | 1.4017 (19) | C18—H18A | 0.9900 |
C2—C3 | 1.390 (2) | C18—H18B | 0.9900 |
C3—C4 | 1.387 (2) | C19—C20 | 1.525 (2) |
C4—C5 | 1.378 (2) | C19—H19A | 0.9900 |
C5—C6 | 1.3987 (19) | C19—H19B | 0.9900 |
C7—C8 | 1.3979 (19) | C20—C21 | 1.524 (2) |
C7—C12 | 1.402 (2) | C20—H20A | 0.9900 |
C8—C9 | 1.393 (2) | C20—H20B | 0.9900 |
C8—H8 | 0.9500 | C21—C22 | 1.526 (2) |
C9—C10 | 1.396 (2) | C21—H21A | 0.9900 |
C9—H9 | 0.9500 | C21—H21B | 0.9900 |
C10—C11 | 1.403 (2) | C22—C23 | 1.524 (2) |
C11—C12 | 1.375 (2) | C22—H22A | 0.9900 |
C11—H11 | 0.9500 | C22—H22B | 0.9900 |
C12—H12 | 0.9500 | C23—C24 | 1.521 (2) |
C13—C14 | 1.507 (2) | C23—H23A | 0.9900 |
C13—H13A | 0.9900 | C23—H23B | 0.9900 |
C13—H13B | 0.9900 | C24—H24A | 0.9800 |
C14—C15 | 1.521 (2) | C24—H24B | 0.9800 |
C14—H14A | 0.9900 | C24—H24C | 0.9800 |
C10—O1—C13 | 118.62 (11) | H15A—C15—H15B | 107.8 |
N2—N1—C6 | 115.12 (12) | C15—C16—C17 | 114.19 (12) |
N1—N2—C7 | 113.08 (12) | C15—C16—H16A | 108.7 |
F1—C1—C2 | 116.96 (12) | C17—C16—H16A | 108.7 |
F1—C1—C6 | 121.80 (12) | C15—C16—H16B | 108.7 |
C2—C1—C6 | 121.25 (12) | C17—C16—H16B | 108.7 |
F2—C2—C1 | 118.10 (13) | H16A—C16—H16B | 107.6 |
F2—C2—C3 | 120.09 (13) | C16—C17—C18 | 113.17 (12) |
C1—C2—C3 | 121.80 (13) | C16—C17—H17A | 108.9 |
C4—C3—C2 | 117.35 (13) | C18—C17—H17A | 108.9 |
C4—C3—I1 | 121.22 (10) | C16—C17—H17B | 108.9 |
C2—C3—I1 | 121.43 (11) | C18—C17—H17B | 108.9 |
F3—C4—C5 | 118.79 (13) | H17A—C17—H17B | 107.8 |
F3—C4—C3 | 120.11 (13) | C17—C18—C19 | 113.60 (12) |
C5—C4—C3 | 121.08 (13) | C17—C18—H18A | 108.8 |
F4—C5—C4 | 118.44 (12) | C19—C18—H18A | 108.8 |
F4—C5—C6 | 119.31 (12) | C17—C18—H18B | 108.8 |
C4—C5—C6 | 122.24 (13) | C19—C18—H18B | 108.8 |
C5—C6—C1 | 116.27 (12) | H18A—C18—H18B | 107.7 |
C5—C6—N1 | 115.16 (12) | C20—C19—C18 | 114.63 (12) |
C1—C6—N1 | 128.56 (12) | C20—C19—H19A | 108.6 |
C8—C7—C12 | 119.95 (13) | C18—C19—H19A | 108.6 |
C8—C7—N2 | 115.66 (12) | C20—C19—H19B | 108.6 |
C12—C7—N2 | 124.38 (13) | C18—C19—H19B | 108.6 |
C9—C8—C7 | 120.77 (13) | H19A—C19—H19B | 107.6 |
C9—C8—H8 | 119.6 | C21—C20—C19 | 112.15 (12) |
C7—C8—H8 | 119.6 | C21—C20—H20A | 109.2 |
C8—C9—C10 | 118.83 (13) | C19—C20—H20A | 109.2 |
C8—C9—H9 | 120.6 | C21—C20—H20B | 109.2 |
C10—C9—H9 | 120.6 | C19—C20—H20B | 109.2 |
O1—C10—C9 | 124.98 (13) | H20A—C20—H20B | 107.9 |
O1—C10—C11 | 114.78 (12) | C20—C21—C22 | 115.23 (12) |
C9—C10—C11 | 120.24 (13) | C20—C21—H21A | 108.5 |
C12—C11—C10 | 120.82 (13) | C22—C21—H21A | 108.5 |
C12—C11—H11 | 119.6 | C20—C21—H21B | 108.5 |
C10—C11—H11 | 119.6 | C22—C21—H21B | 108.5 |
C11—C12—C7 | 119.37 (13) | H21A—C21—H21B | 107.5 |
C11—C12—H12 | 120.3 | C23—C22—C21 | 111.26 (12) |
C7—C12—H12 | 120.3 | C23—C22—H22A | 109.4 |
O1—C13—C14 | 106.98 (11) | C21—C22—H22A | 109.4 |
O1—C13—H13A | 110.3 | C23—C22—H22B | 109.4 |
C14—C13—H13A | 110.3 | C21—C22—H22B | 109.4 |
O1—C13—H13B | 110.3 | H22A—C22—H22B | 108.0 |
C14—C13—H13B | 110.3 | C24—C23—C22 | 114.72 (13) |
H13A—C13—H13B | 108.6 | C24—C23—H23A | 108.6 |
C13—C14—C15 | 112.62 (12) | C22—C23—H23A | 108.6 |
C13—C14—H14A | 109.1 | C24—C23—H23B | 108.6 |
C15—C14—H14A | 109.1 | C22—C23—H23B | 108.6 |
C13—C14—H14B | 109.1 | H23A—C23—H23B | 107.6 |
C15—C14—H14B | 109.1 | C23—C24—H24A | 109.5 |
H14A—C14—H14B | 107.8 | C23—C24—H24B | 109.5 |
C16—C15—C14 | 112.88 (12) | H24A—C24—H24B | 109.5 |
C16—C15—H15A | 109.0 | C23—C24—H24C | 109.5 |
C14—C15—H15A | 109.0 | H24A—C24—H24C | 109.5 |
C16—C15—H15B | 109.0 | H24B—C24—H24C | 109.5 |
C14—C15—H15B | 109.0 | ||
C6—N1—N2—C7 | 179.24 (12) | N2—N1—C6—C1 | −2.6 (2) |
F1—C1—C2—F2 | 0.0 (2) | N1—N2—C7—C8 | 173.55 (13) |
C6—C1—C2—F2 | 179.77 (13) | N1—N2—C7—C12 | −7.7 (2) |
F1—C1—C2—C3 | −179.22 (13) | C12—C7—C8—C9 | 1.7 (2) |
C6—C1—C2—C3 | 0.5 (2) | N2—C7—C8—C9 | −179.53 (14) |
F2—C2—C3—C4 | 179.74 (13) | C7—C8—C9—C10 | −1.1 (2) |
C1—C2—C3—C4 | −1.0 (2) | C13—O1—C10—C9 | −0.7 (2) |
F2—C2—C3—I1 | −1.13 (19) | C13—O1—C10—C11 | 179.93 (13) |
C1—C2—C3—I1 | 178.11 (11) | C8—C9—C10—O1 | −179.60 (14) |
C2—C3—C4—F3 | 179.21 (13) | C8—C9—C10—C11 | −0.3 (2) |
I1—C3—C4—F3 | 0.07 (19) | O1—C10—C11—C12 | −179.53 (14) |
C2—C3—C4—C5 | 0.7 (2) | C9—C10—C11—C12 | 1.1 (2) |
I1—C3—C4—C5 | −178.40 (11) | C10—C11—C12—C7 | −0.5 (2) |
F3—C4—C5—F4 | 0.6 (2) | C8—C7—C12—C11 | −0.9 (2) |
C3—C4—C5—F4 | 179.11 (13) | N2—C7—C12—C11 | −179.55 (14) |
F3—C4—C5—C6 | −178.43 (13) | C10—O1—C13—C14 | 177.97 (13) |
C3—C4—C5—C6 | 0.1 (2) | O1—C13—C14—C15 | 177.40 (12) |
F4—C5—C6—C1 | −179.62 (12) | C13—C14—C15—C16 | 179.64 (13) |
C4—C5—C6—C1 | −0.6 (2) | C14—C15—C16—C17 | 177.19 (13) |
F4—C5—C6—N1 | −0.16 (19) | C15—C16—C17—C18 | 178.86 (13) |
C4—C5—C6—N1 | 178.88 (13) | C16—C17—C18—C19 | 177.46 (13) |
F1—C1—C6—C5 | −179.99 (13) | C17—C18—C19—C20 | −179.94 (13) |
C2—C1—C6—C5 | 0.3 (2) | C18—C19—C20—C21 | 179.44 (13) |
F1—C1—C6—N1 | 0.6 (2) | C19—C20—C21—C22 | 177.18 (13) |
C2—C1—C6—N1 | −179.08 (14) | C20—C21—C22—C23 | 178.26 (14) |
N2—N1—C6—C5 | 178.07 (13) | C21—C22—C23—C24 | −179.46 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9···F1i | 0.95 | 2.59 | 3.1477 (17) | 118 |
Symmetry code: (i) −x, −y, −z. |
C24H29F4IN2O | F(000) = 1136 |
Mr = 564.39 | Dx = 1.571 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 7540 reflections |
a = 8.5802 (16) Å | θ = 2.6–26.9° |
b = 33.663 (5) Å | µ = 1.39 mm−1 |
c = 8.752 (2) Å | T = 103 K |
β = 109.255 (16)° | Lamina, orange |
V = 2386.5 (8) Å3 | 0.20 × 0.10 × 0.05 mm |
Z = 4 |
Bruker APEX-II CCD diffractometer | 5073 independent reflections |
Radiation source: fine-focus sealed tube | 3840 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
φ and ω scans | θmax = 27.5°, θmin = 2.4° |
Absorption correction: multi-scan Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. | h = −11→10 |
Tmin = 0.791, Tmax = 0.862 | k = −43→42 |
25224 measured reflections | l = −11→10 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.059 | H-atom parameters not refined |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0132P)2 + 3.0191P] where P = (Fo2 + 2Fc2)/3 |
5073 reflections | (Δ/σ)max = 0.004 |
290 parameters | Δρmax = 0.57 e Å−3 |
0 restraints | Δρmin = −0.99 e Å−3 |
Experimental. Crystals were orange thin plate, nearly always twinned. The champion used for data collection was an untwinned portion cut from a large twinned crystal. The experiment temperature was controlled by a Bruker KRYOFLEX low temperature device. |
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. |
x | y | z | Uiso*/Ueq | ||
I1 | −0.33486 (3) | 0.719707 (6) | 0.50898 (2) | 0.01803 (6) | |
C1 | 0.0686 (4) | 0.69226 (9) | 0.9478 (3) | 0.0146 (7) | |
C2 | −0.0729 (4) | 0.69065 (9) | 0.8160 (4) | 0.0151 (7) | |
C3 | −0.1316 (4) | 0.72358 (9) | 0.7209 (3) | 0.0152 (6) | |
C4 | −0.0458 (4) | 0.75871 (9) | 0.7667 (4) | 0.0167 (7) | |
C5 | 0.0956 (4) | 0.76055 (9) | 0.8995 (4) | 0.0162 (7) | |
C6 | 0.1587 (4) | 0.72706 (8) | 0.9900 (3) | 0.0143 (6) | |
F1 | 0.1189 (2) | 0.65949 (5) | 1.0380 (2) | 0.0204 (4) | |
F2 | −0.1538 (2) | 0.65581 (5) | 0.7814 (2) | 0.0217 (4) | |
F3 | −0.0999 (2) | 0.79237 (5) | 0.6820 (2) | 0.0221 (4) | |
F4 | 0.1772 (2) | 0.79515 (5) | 0.9384 (2) | 0.0225 (4) | |
N1 | 0.2931 (3) | 0.73196 (7) | 1.1398 (3) | 0.0166 (6) | |
N2 | 0.4156 (3) | 0.70914 (7) | 1.1791 (3) | 0.0167 (6) | |
C7 | 0.4508 (4) | 0.67991 (9) | 1.0768 (3) | 0.0149 (7) | |
C8 | 0.5412 (4) | 0.64763 (9) | 1.1593 (4) | 0.0170 (7) | |
H8 | 0.5695 | 0.6461 | 1.2736 | 0.020* | |
C9 | 0.5899 (4) | 0.61800 (9) | 1.0770 (4) | 0.0182 (7) | |
H9 | 0.6482 | 0.5956 | 1.1341 | 0.022* | |
C10 | 0.5542 (4) | 0.62068 (9) | 0.9107 (4) | 0.0168 (7) | |
C11 | 0.4685 (4) | 0.65333 (9) | 0.8273 (4) | 0.0162 (7) | |
H11 | 0.4451 | 0.6554 | 0.7137 | 0.019* | |
C12 | 0.4169 (4) | 0.68300 (9) | 0.9102 (3) | 0.0152 (7) | |
H12 | 0.3585 | 0.7054 | 0.8533 | 0.018* | |
O1 | 0.6138 (3) | 0.59014 (6) | 0.8444 (2) | 0.0206 (5) | |
C13 | 0.5739 (4) | 0.58791 (9) | 0.6719 (4) | 0.0188 (7) | |
H13A | 0.6000 | 0.6133 | 0.6290 | 0.023* | |
H13B | 0.4549 | 0.5822 | 0.6197 | 0.023* | |
C14 | 0.6770 (4) | 0.55465 (9) | 0.6391 (4) | 0.0190 (7) | |
H14A | 0.6637 | 0.5307 | 0.6991 | 0.023* | |
H14B | 0.7948 | 0.5624 | 0.6802 | 0.023* | |
C15 | 0.6298 (4) | 0.54457 (9) | 0.4600 (4) | 0.0181 (7) | |
H15A | 0.5173 | 0.5331 | 0.4228 | 0.022* | |
H15B | 0.6271 | 0.5694 | 0.3982 | 0.022* | |
C16 | 0.7479 (4) | 0.51547 (9) | 0.4231 (4) | 0.0200 (7) | |
H16A | 0.7582 | 0.4917 | 0.4925 | 0.024* | |
H16B | 0.8583 | 0.5280 | 0.4520 | 0.024* | |
C17 | 0.6956 (4) | 0.50221 (9) | 0.2471 (4) | 0.0199 (7) | |
H17A | 0.5931 | 0.4864 | 0.2225 | 0.024* | |
H17B | 0.6703 | 0.5260 | 0.1768 | 0.024* | |
C18 | 0.8253 (4) | 0.47760 (9) | 0.2061 (4) | 0.0195 (7) | |
H18A | 0.9278 | 0.4934 | 0.2298 | 0.023* | |
H18B | 0.8511 | 0.4538 | 0.2763 | 0.023* | |
C19 | 0.7702 (4) | 0.46457 (9) | 0.0302 (4) | 0.0190 (7) | |
H19A | 0.7359 | 0.4883 | −0.0394 | 0.023* | |
H19B | 0.6723 | 0.4472 | 0.0092 | 0.023* | |
C20 | 0.9012 (4) | 0.44251 (9) | −0.0185 (4) | 0.0187 (7) | |
H20A | 0.9970 | 0.4603 | −0.0038 | 0.022* | |
H20B | 0.9395 | 0.4193 | 0.0536 | 0.022* | |
C21 | 0.8373 (4) | 0.42840 (9) | −0.1932 (4) | 0.0185 (7) | |
H21A | 0.7895 | 0.4514 | −0.2634 | 0.022* | |
H21B | 0.7471 | 0.4091 | −0.2046 | 0.022* | |
C22 | 0.9665 (4) | 0.40908 (9) | −0.2537 (4) | 0.0194 (7) | |
H22A | 1.0522 | 0.4289 | −0.2519 | 0.023* | |
H22B | 1.0206 | 0.3872 | −0.1797 | 0.023* | |
C23 | 0.8925 (4) | 0.39274 (10) | −0.4243 (4) | 0.0215 (7) | |
H23A | 0.8372 | 0.4147 | −0.4976 | 0.026* | |
H23B | 0.8072 | 0.3728 | −0.4254 | 0.026* | |
C24 | 1.0181 (5) | 0.37354 (10) | −0.4895 (4) | 0.0291 (8) | |
H24A | 1.0753 | 0.3521 | −0.4167 | 0.044* | |
H24B | 1.0987 | 0.3935 | −0.4965 | 0.044* | |
H24C | 0.9615 | 0.3626 | −0.5974 | 0.044* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.01436 (10) | 0.02283 (11) | 0.01573 (10) | 0.00240 (11) | 0.00336 (7) | −0.00071 (10) |
C1 | 0.0150 (17) | 0.0163 (17) | 0.0141 (15) | 0.0046 (14) | 0.0069 (13) | 0.0024 (13) |
C2 | 0.0165 (17) | 0.0133 (17) | 0.0186 (16) | −0.0038 (14) | 0.0099 (14) | −0.0038 (13) |
C3 | 0.0128 (15) | 0.0209 (17) | 0.0127 (14) | 0.0018 (15) | 0.0052 (12) | −0.0016 (13) |
C4 | 0.0207 (18) | 0.0151 (17) | 0.0168 (16) | 0.0046 (15) | 0.0095 (14) | 0.0046 (13) |
C5 | 0.0199 (18) | 0.0115 (16) | 0.0199 (16) | −0.0011 (15) | 0.0102 (14) | −0.0022 (13) |
C6 | 0.0135 (15) | 0.0155 (17) | 0.0153 (15) | 0.0005 (14) | 0.0067 (12) | −0.0055 (12) |
F1 | 0.0216 (10) | 0.0151 (9) | 0.0224 (10) | 0.0002 (8) | 0.0044 (8) | 0.0053 (7) |
F2 | 0.0196 (10) | 0.0185 (10) | 0.0247 (10) | −0.0052 (8) | 0.0041 (8) | −0.0011 (8) |
F3 | 0.0256 (11) | 0.0166 (10) | 0.0231 (10) | 0.0046 (8) | 0.0067 (8) | 0.0054 (7) |
F4 | 0.0242 (11) | 0.0129 (9) | 0.0275 (10) | −0.0030 (8) | 0.0047 (8) | −0.0020 (8) |
N1 | 0.0155 (15) | 0.0174 (15) | 0.0150 (13) | −0.0017 (11) | 0.0025 (11) | −0.0028 (10) |
N2 | 0.0169 (15) | 0.0153 (15) | 0.0174 (13) | 0.0008 (11) | 0.0048 (11) | −0.0015 (10) |
C7 | 0.0124 (16) | 0.0164 (16) | 0.0157 (15) | −0.0029 (14) | 0.0044 (13) | −0.0017 (13) |
C8 | 0.0169 (18) | 0.0208 (18) | 0.0123 (15) | −0.0003 (14) | 0.0033 (13) | −0.0011 (13) |
C9 | 0.0163 (18) | 0.0193 (17) | 0.0170 (16) | 0.0011 (14) | 0.0028 (13) | 0.0032 (13) |
C10 | 0.0147 (17) | 0.0169 (17) | 0.0197 (16) | −0.0022 (14) | 0.0070 (13) | −0.0016 (13) |
C11 | 0.0156 (17) | 0.0204 (18) | 0.0128 (15) | 0.0008 (14) | 0.0051 (13) | 0.0015 (13) |
C12 | 0.0118 (16) | 0.0151 (16) | 0.0175 (16) | −0.0006 (13) | 0.0031 (13) | 0.0028 (13) |
O1 | 0.0285 (13) | 0.0184 (12) | 0.0168 (11) | 0.0063 (10) | 0.0101 (10) | −0.0010 (9) |
C13 | 0.0175 (18) | 0.0215 (18) | 0.0179 (17) | −0.0026 (15) | 0.0062 (14) | −0.0021 (13) |
C14 | 0.0223 (19) | 0.0178 (17) | 0.0186 (17) | 0.0028 (15) | 0.0090 (14) | 0.0014 (13) |
C15 | 0.0170 (18) | 0.0163 (17) | 0.0204 (17) | 0.0001 (14) | 0.0053 (14) | −0.0019 (13) |
C16 | 0.0221 (19) | 0.0192 (18) | 0.0204 (17) | 0.0030 (15) | 0.0092 (14) | 0.0006 (13) |
C17 | 0.0207 (18) | 0.0203 (18) | 0.0201 (17) | −0.0007 (15) | 0.0085 (14) | −0.0014 (13) |
C18 | 0.0254 (19) | 0.0153 (17) | 0.0183 (16) | 0.0041 (15) | 0.0081 (14) | 0.0013 (13) |
C19 | 0.0209 (19) | 0.0168 (17) | 0.0196 (17) | 0.0012 (15) | 0.0070 (14) | −0.0016 (13) |
C20 | 0.0204 (18) | 0.0172 (17) | 0.0180 (16) | −0.0012 (15) | 0.0057 (14) | −0.0016 (13) |
C21 | 0.0205 (18) | 0.0177 (17) | 0.0180 (16) | 0.0019 (14) | 0.0073 (14) | 0.0014 (13) |
C22 | 0.0193 (19) | 0.0180 (17) | 0.0209 (17) | −0.0015 (15) | 0.0067 (14) | 0.0024 (13) |
C23 | 0.0230 (19) | 0.0200 (18) | 0.0227 (18) | 0.0015 (15) | 0.0093 (15) | −0.0011 (14) |
C24 | 0.033 (2) | 0.027 (2) | 0.033 (2) | −0.0037 (17) | 0.0190 (17) | −0.0067 (16) |
I1—C3 | 2.090 (3) | C14—H14B | 0.9900 |
C1—F1 | 1.343 (3) | C15—C16 | 1.519 (4) |
C1—C2 | 1.372 (4) | C15—H15A | 0.9900 |
C1—C6 | 1.385 (4) | C15—H15B | 0.9900 |
C2—F2 | 1.345 (3) | C16—C17 | 1.523 (4) |
C2—C3 | 1.378 (4) | C16—H16A | 0.9900 |
C3—C4 | 1.380 (4) | C16—H16B | 0.9900 |
C4—F3 | 1.350 (3) | C17—C18 | 1.522 (4) |
C4—C5 | 1.378 (4) | C17—H17A | 0.9900 |
C5—F4 | 1.344 (3) | C17—H17B | 0.9900 |
C5—C6 | 1.381 (4) | C18—C19 | 1.519 (4) |
C6—N1 | 1.442 (4) | C18—H18A | 0.9900 |
N1—N2 | 1.255 (3) | C18—H18B | 0.9900 |
N2—C7 | 1.429 (4) | C19—C20 | 1.520 (4) |
C7—C8 | 1.391 (4) | C19—H19A | 0.9900 |
C7—C12 | 1.393 (4) | C19—H19B | 0.9900 |
C8—C9 | 1.374 (4) | C20—C21 | 1.520 (4) |
C8—H8 | 0.9500 | C20—H20A | 0.9900 |
C9—C10 | 1.388 (4) | C20—H20B | 0.9900 |
C9—H9 | 0.9500 | C21—C22 | 1.524 (4) |
C10—O1 | 1.360 (4) | C21—H21A | 0.9900 |
C10—C11 | 1.389 (4) | C21—H21B | 0.9900 |
C11—C12 | 1.390 (4) | C22—C23 | 1.520 (4) |
C11—H11 | 0.9500 | C22—H22A | 0.9900 |
C12—H12 | 0.9500 | C22—H22B | 0.9900 |
O1—C13 | 1.435 (3) | C23—C24 | 1.520 (4) |
C13—C14 | 1.512 (4) | C23—H23A | 0.9900 |
C13—H13A | 0.9900 | C23—H23B | 0.9900 |
C13—H13B | 0.9900 | C24—H24A | 0.9800 |
C14—C15 | 1.522 (4) | C24—H24B | 0.9800 |
C14—H14A | 0.9900 | C24—H24C | 0.9800 |
F1—C1—C2 | 119.1 (3) | H15A—C15—H15B | 107.8 |
F1—C1—C6 | 119.7 (3) | C15—C16—C17 | 114.2 (3) |
C2—C1—C6 | 121.3 (3) | C15—C16—H16A | 108.7 |
F2—C2—C1 | 118.1 (3) | C17—C16—H16A | 108.7 |
F2—C2—C3 | 120.5 (3) | C15—C16—H16B | 108.7 |
C1—C2—C3 | 121.4 (3) | C17—C16—H16B | 108.7 |
C2—C3—C4 | 117.4 (3) | H16A—C16—H16B | 107.6 |
C2—C3—I1 | 121.2 (2) | C18—C17—C16 | 113.8 (3) |
C4—C3—I1 | 121.3 (2) | C18—C17—H17A | 108.8 |
F3—C4—C5 | 118.3 (3) | C16—C17—H17A | 108.8 |
F3—C4—C3 | 120.4 (3) | C18—C17—H17B | 108.8 |
C5—C4—C3 | 121.3 (3) | C16—C17—H17B | 108.8 |
F4—C5—C4 | 119.5 (3) | H17A—C17—H17B | 107.7 |
F4—C5—C6 | 119.3 (3) | C19—C18—C17 | 112.9 (3) |
C4—C5—C6 | 121.1 (3) | C19—C18—H18A | 109.0 |
C5—C6—C1 | 117.3 (3) | C17—C18—H18A | 109.0 |
C5—C6—N1 | 118.2 (3) | C19—C18—H18B | 109.0 |
C1—C6—N1 | 123.2 (3) | C17—C18—H18B | 109.0 |
N2—N1—C6 | 121.7 (2) | H18A—C18—H18B | 107.8 |
N1—N2—C7 | 125.5 (2) | C18—C19—C20 | 114.4 (3) |
C8—C7—C12 | 119.4 (3) | C18—C19—H19A | 108.7 |
C8—C7—N2 | 114.2 (3) | C20—C19—H19A | 108.7 |
C12—C7—N2 | 126.2 (3) | C18—C19—H19B | 108.7 |
C9—C8—C7 | 120.6 (3) | C20—C19—H19B | 108.7 |
C9—C8—H8 | 119.7 | H19A—C19—H19B | 107.6 |
C7—C8—H8 | 119.7 | C21—C20—C19 | 112.3 (3) |
C8—C9—C10 | 120.2 (3) | C21—C20—H20A | 109.1 |
C8—C9—H9 | 119.9 | C19—C20—H20A | 109.1 |
C10—C9—H9 | 119.9 | C21—C20—H20B | 109.1 |
O1—C10—C9 | 114.5 (3) | C19—C20—H20B | 109.1 |
O1—C10—C11 | 125.6 (3) | H20A—C20—H20B | 107.9 |
C9—C10—C11 | 119.8 (3) | C20—C21—C22 | 114.9 (3) |
C10—C11—C12 | 120.0 (3) | C20—C21—H21A | 108.5 |
C10—C11—H11 | 120.0 | C22—C21—H21A | 108.5 |
C12—C11—H11 | 120.0 | C20—C21—H21B | 108.5 |
C11—C12—C7 | 120.0 (3) | C22—C21—H21B | 108.5 |
C11—C12—H12 | 120.0 | H21A—C21—H21B | 107.5 |
C7—C12—H12 | 120.0 | C23—C22—C21 | 112.3 (3) |
C10—O1—C13 | 119.7 (2) | C23—C22—H22A | 109.1 |
O1—C13—C14 | 106.7 (2) | C21—C22—H22A | 109.1 |
O1—C13—H13A | 110.4 | C23—C22—H22B | 109.1 |
C14—C13—H13A | 110.4 | C21—C22—H22B | 109.1 |
O1—C13—H13B | 110.4 | H22A—C22—H22B | 107.9 |
C14—C13—H13B | 110.4 | C22—C23—C24 | 113.9 (3) |
H13A—C13—H13B | 108.6 | C22—C23—H23A | 108.8 |
C13—C14—C15 | 112.8 (3) | C24—C23—H23A | 108.8 |
C13—C14—H14A | 109.0 | C22—C23—H23B | 108.8 |
C15—C14—H14A | 109.0 | C24—C23—H23B | 108.8 |
C13—C14—H14B | 109.0 | H23A—C23—H23B | 107.7 |
C15—C14—H14B | 109.0 | C23—C24—H24A | 109.5 |
H14A—C14—H14B | 107.8 | C23—C24—H24B | 109.5 |
C16—C15—C14 | 113.1 (2) | H24A—C24—H24B | 109.5 |
C16—C15—H15A | 109.0 | C23—C24—H24C | 109.5 |
C14—C15—H15A | 109.0 | H24A—C24—H24C | 109.5 |
C16—C15—H15B | 109.0 | H24B—C24—H24C | 109.5 |
C14—C15—H15B | 109.0 | ||
F1—C1—C2—F2 | −1.1 (4) | C6—N1—N2—C7 | 9.3 (4) |
C6—C1—C2—F2 | 179.6 (3) | N1—N2—C7—C8 | −152.1 (3) |
F1—C1—C2—C3 | 178.9 (3) | N1—N2—C7—C12 | 34.3 (5) |
C6—C1—C2—C3 | −0.3 (5) | C12—C7—C8—C9 | −3.2 (5) |
F2—C2—C3—C4 | 177.7 (3) | N2—C7—C8—C9 | −177.3 (3) |
C1—C2—C3—C4 | −2.3 (4) | C7—C8—C9—C10 | 2.3 (5) |
F2—C2—C3—I1 | −5.5 (4) | C8—C9—C10—O1 | 177.9 (3) |
C1—C2—C3—I1 | 174.5 (2) | C8—C9—C10—C11 | −0.3 (5) |
C2—C3—C4—F3 | −177.7 (3) | O1—C10—C11—C12 | −178.7 (3) |
I1—C3—C4—F3 | 5.5 (4) | C9—C10—C11—C12 | −0.8 (5) |
C2—C3—C4—C5 | 1.8 (4) | C10—C11—C12—C7 | −0.2 (5) |
I1—C3—C4—C5 | −174.9 (2) | C8—C7—C12—C11 | 2.2 (4) |
F3—C4—C5—F4 | −1.6 (4) | N2—C7—C12—C11 | 175.5 (3) |
C3—C4—C5—F4 | 178.8 (3) | C9—C10—O1—C13 | 175.1 (3) |
F3—C4—C5—C6 | −179.1 (3) | C11—C10—O1—C13 | −6.9 (5) |
C3—C4—C5—C6 | 1.3 (5) | C10—O1—C13—C14 | 172.0 (3) |
F4—C5—C6—C1 | 178.6 (3) | O1—C13—C14—C15 | 171.5 (3) |
C4—C5—C6—C1 | −3.9 (5) | C13—C14—C15—C16 | 171.8 (3) |
F4—C5—C6—N1 | 11.0 (4) | C14—C15—C16—C17 | 175.1 (3) |
C4—C5—C6—N1 | −171.5 (3) | C15—C16—C17—C18 | 172.1 (3) |
F1—C1—C6—C5 | −175.8 (3) | C16—C17—C18—C19 | 179.8 (3) |
C2—C1—C6—C5 | 3.4 (5) | C17—C18—C19—C20 | 175.7 (3) |
F1—C1—C6—N1 | −8.9 (4) | C18—C19—C20—C21 | 177.2 (3) |
C2—C1—C6—N1 | 170.4 (3) | C19—C20—C21—C22 | 175.2 (3) |
C5—C6—N1—N2 | −136.4 (3) | C20—C21—C22—C23 | 175.5 (3) |
C1—C6—N1—N2 | 56.8 (4) | C21—C22—C23—C24 | 179.5 (3) |
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