The structures of three iodochalcones, functionalized with fluorine or a nitro group, have been investigated to explore the impact of different molecular electrostatic distributions on the halogen bonding within each crystal structure. The strongly withdrawing nitro group presented a switch of the halogen bond from a lateral to a linear motif. Surprisingly, this appears to be influenced by a net positive shift in charge distribution around the lateral edges of the σ-hole, making the lateral I
I bonding motif less preferable. A channel of amphoteric I
I type II halogen bonds is observed for a chalcone molecule, which was not previously reported in chalcones, alongside an example of the common synthon involving extended linear chains of I
O
2N donor–acceptor halogen bonds. This work shows that halogenated chalcones may be an interesting target for developing halogen bonding as a significant tool within crystal engineering, a thus far underexplored area for this common structural motif.
Supporting information
CCDC references: 2050700; 2050701; 2050702
For all structures, data collection: APEX2 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016). Program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007; Palatinus & van der Lee, 2008; Palatinus et al., 2012) for ep2o, ep8p; SHELXT (Sheldrick, 2015a) for ep2m. For all structures, program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
(2
E)-3-(2-Fluorophenyl)-1-(4-iodophenyl)prop-2-en-1-one (ep2o)
top
Crystal data top
C15H10FIO | F(000) = 680 |
Mr = 352.13 | Dx = 1.769 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 22.9802 (10) Å | Cell parameters from 4157 reflections |
b = 4.7448 (2) Å | θ = 2.7–27.8° |
c = 12.2026 (6) Å | µ = 2.42 mm−1 |
β = 96.534 (2)° | T = 100 K |
V = 1321.89 (10) Å3 | Block, clear colourless |
Z = 4 | 0.48 × 0.28 × 0.18 mm |
Data collection top
Bruker APEXII Kappa CCD area detector diffractometer | 3019 independent reflections |
Radiation source: fine-focus sealed tube | 2628 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
φ and ω scans | θmax = 27.5°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −29→29 |
Tmin = 0.606, Tmax = 0.746 | k = −6→6 |
10963 measured reflections | l = −8→15 |
Refinement top
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Secondary atom site location: diffmap |
R[F2 > 2σ(F2)] = 0.024 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.057 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0285P)2 + 0.2311P] where P = (Fo2 + 2Fc2)/3 |
3019 reflections | (Δ/σ)max = 0.003 |
163 parameters | Δρmax = 0.66 e Å−3 |
0 restraints | Δρmin = −0.52 e Å−3 |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
I1 | 0.95514 (2) | 0.08114 (4) | 0.32982 (2) | 0.02230 (7) | |
F1 | 0.57442 (7) | 1.4067 (3) | 0.52807 (12) | 0.0303 (4) | |
O1 | 0.74598 (9) | 0.8128 (5) | 0.60332 (14) | 0.0330 (5) | |
C1 | 0.75618 (11) | 0.8393 (6) | 0.5071 (2) | 0.0214 (5) | |
C2 | 0.72235 (11) | 1.0410 (5) | 0.4316 (2) | 0.0203 (5) | |
H2 | 0.734452 | 1.075180 | 0.360920 | 0.024* | |
C3 | 0.67557 (11) | 1.1752 (5) | 0.46031 (19) | 0.0202 (5) | |
H3 | 0.664083 | 1.133601 | 0.530901 | 0.024* | |
C4 | 0.80339 (11) | 0.6695 (5) | 0.46366 (19) | 0.0188 (5) | |
C5 | 0.84511 (12) | 0.5329 (6) | 0.5388 (2) | 0.0235 (6) | |
H5 | 0.843674 | 0.556098 | 0.615760 | 0.028* | |
C6 | 0.88826 (12) | 0.3649 (6) | 0.5021 (2) | 0.0236 (6) | |
H6 | 0.916431 | 0.274472 | 0.553348 | 0.028* | |
C7 | 0.88983 (11) | 0.3304 (5) | 0.38914 (19) | 0.0187 (5) | |
C8 | 0.84888 (11) | 0.4611 (5) | 0.3131 (2) | 0.0205 (5) | |
H8 | 0.849921 | 0.433193 | 0.236282 | 0.025* | |
C9 | 0.80618 (11) | 0.6337 (5) | 0.35095 (19) | 0.0199 (5) | |
H9 | 0.778759 | 0.727833 | 0.299359 | 0.024* | |
C10 | 0.64031 (11) | 1.3807 (5) | 0.39290 (19) | 0.0183 (5) | |
C11 | 0.59061 (11) | 1.5000 (6) | 0.4304 (2) | 0.0208 (5) | |
C12 | 0.55626 (11) | 1.7033 (6) | 0.3732 (2) | 0.0250 (6) | |
H12 | 0.522972 | 1.778946 | 0.402357 | 0.030* | |
C13 | 0.57147 (12) | 1.7939 (6) | 0.2726 (2) | 0.0260 (6) | |
H13 | 0.548837 | 1.934627 | 0.232041 | 0.031* | |
C14 | 0.62004 (12) | 1.6782 (6) | 0.2310 (2) | 0.0246 (6) | |
H14 | 0.630073 | 1.738765 | 0.161324 | 0.029* | |
C15 | 0.65387 (11) | 1.4765 (5) | 0.2896 (2) | 0.0207 (5) | |
H15 | 0.686931 | 1.400827 | 0.259677 | 0.025* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.02079 (10) | 0.02608 (10) | 0.02034 (10) | 0.00181 (7) | 0.00365 (6) | 0.00239 (7) |
F1 | 0.0324 (9) | 0.0377 (10) | 0.0228 (8) | −0.0026 (7) | 0.0118 (6) | −0.0023 (7) |
O1 | 0.0399 (12) | 0.0464 (13) | 0.0130 (9) | 0.0138 (10) | 0.0048 (8) | 0.0026 (9) |
C1 | 0.0244 (13) | 0.0233 (13) | 0.0159 (12) | −0.0018 (10) | −0.0006 (10) | −0.0015 (10) |
C2 | 0.0265 (13) | 0.0203 (13) | 0.0143 (11) | −0.0019 (11) | 0.0038 (10) | −0.0002 (10) |
C3 | 0.0244 (13) | 0.0230 (13) | 0.0129 (11) | −0.0034 (10) | 0.0013 (9) | −0.0013 (10) |
C4 | 0.0209 (13) | 0.0204 (12) | 0.0151 (11) | −0.0032 (10) | 0.0015 (9) | 0.0015 (10) |
C5 | 0.0294 (14) | 0.0277 (14) | 0.0129 (11) | 0.0022 (12) | 0.0009 (10) | 0.0005 (10) |
C6 | 0.0269 (14) | 0.0263 (14) | 0.0166 (12) | 0.0022 (11) | −0.0020 (10) | 0.0040 (10) |
C7 | 0.0203 (12) | 0.0191 (12) | 0.0168 (12) | −0.0004 (10) | 0.0022 (9) | 0.0003 (10) |
C8 | 0.0236 (13) | 0.0248 (14) | 0.0134 (11) | −0.0010 (11) | 0.0028 (9) | 0.0010 (10) |
C9 | 0.0230 (13) | 0.0221 (13) | 0.0138 (11) | 0.0005 (10) | −0.0009 (9) | 0.0035 (9) |
C10 | 0.0188 (12) | 0.0189 (12) | 0.0168 (12) | −0.0029 (10) | 0.0000 (9) | −0.0033 (9) |
C11 | 0.0234 (13) | 0.0226 (13) | 0.0170 (11) | −0.0065 (10) | 0.0050 (10) | −0.0046 (10) |
C12 | 0.0182 (12) | 0.0259 (14) | 0.0311 (14) | −0.0002 (11) | 0.0040 (10) | −0.0073 (12) |
C13 | 0.0262 (14) | 0.0239 (14) | 0.0259 (13) | 0.0019 (12) | −0.0050 (10) | −0.0014 (11) |
C14 | 0.0301 (15) | 0.0246 (14) | 0.0187 (12) | −0.0002 (11) | 0.0016 (10) | −0.0001 (11) |
C15 | 0.0217 (13) | 0.0228 (13) | 0.0181 (12) | 0.0012 (10) | 0.0039 (10) | −0.0018 (10) |
Geometric parameters (Å, º) top
I1—C7 | 2.103 (2) | C7—C8 | 1.390 (3) |
F1—C11 | 1.362 (3) | C8—H8 | 0.9500 |
O1—C1 | 1.230 (3) | C8—C9 | 1.396 (4) |
C1—C2 | 1.485 (4) | C9—H9 | 0.9500 |
C1—C4 | 1.496 (4) | C10—C11 | 1.398 (3) |
C2—H2 | 0.9500 | C10—C15 | 1.408 (3) |
C2—C3 | 1.330 (4) | C11—C12 | 1.384 (4) |
C3—H3 | 0.9500 | C12—H12 | 0.9500 |
C3—C10 | 1.460 (3) | C12—C13 | 1.383 (4) |
C4—C5 | 1.407 (4) | C13—H13 | 0.9500 |
C4—C9 | 1.395 (3) | C13—C14 | 1.391 (4) |
C5—H5 | 0.9500 | C14—H14 | 0.9500 |
C5—C6 | 1.386 (4) | C14—C15 | 1.381 (4) |
C6—H6 | 0.9500 | C15—H15 | 0.9500 |
C6—C7 | 1.392 (3) | | |
| | | |
O1—C1—C2 | 121.0 (2) | C9—C8—H8 | 120.4 |
O1—C1—C4 | 120.5 (2) | C4—C9—C8 | 120.7 (2) |
C2—C1—C4 | 118.5 (2) | C4—C9—H9 | 119.7 |
C1—C2—H2 | 119.1 | C8—C9—H9 | 119.7 |
C3—C2—C1 | 121.8 (2) | C11—C10—C3 | 120.5 (2) |
C3—C2—H2 | 119.1 | C11—C10—C15 | 115.8 (2) |
C2—C3—H3 | 117.1 | C15—C10—C3 | 123.7 (2) |
C2—C3—C10 | 125.8 (2) | F1—C11—C10 | 118.0 (2) |
C10—C3—H3 | 117.1 | F1—C11—C12 | 118.1 (2) |
C5—C4—C1 | 119.0 (2) | C12—C11—C10 | 123.9 (2) |
C9—C4—C1 | 122.1 (2) | C11—C12—H12 | 120.7 |
C9—C4—C5 | 118.8 (2) | C13—C12—C11 | 118.5 (2) |
C4—C5—H5 | 119.5 | C13—C12—H12 | 120.7 |
C6—C5—C4 | 120.9 (2) | C12—C13—H13 | 120.1 |
C6—C5—H5 | 119.5 | C12—C13—C14 | 119.7 (2) |
C5—C6—H6 | 120.4 | C14—C13—H13 | 120.1 |
C5—C6—C7 | 119.2 (2) | C13—C14—H14 | 119.6 |
C7—C6—H6 | 120.4 | C15—C14—C13 | 120.8 (2) |
C6—C7—I1 | 120.45 (18) | C15—C14—H14 | 119.6 |
C8—C7—I1 | 118.47 (17) | C10—C15—H15 | 119.4 |
C8—C7—C6 | 121.1 (2) | C14—C15—C10 | 121.3 (2) |
C7—C8—H8 | 120.4 | C14—C15—H15 | 119.4 |
C7—C8—C9 | 119.3 (2) | | |
| | | |
I1—C7—C8—C9 | −178.22 (18) | C4—C1—C2—C3 | 172.2 (2) |
F1—C11—C12—C13 | −178.3 (2) | C4—C5—C6—C7 | −0.4 (4) |
O1—C1—C2—C3 | −8.1 (4) | C5—C4—C9—C8 | 1.3 (4) |
O1—C1—C4—C5 | −15.5 (4) | C5—C6—C7—I1 | 179.3 (2) |
O1—C1—C4—C9 | 162.2 (2) | C5—C6—C7—C8 | −0.1 (4) |
C1—C2—C3—C10 | 178.7 (2) | C6—C7—C8—C9 | 1.2 (4) |
C1—C4—C5—C6 | 177.6 (2) | C7—C8—C9—C4 | −1.8 (4) |
C1—C4—C9—C8 | −176.4 (2) | C9—C4—C5—C6 | −0.2 (4) |
C2—C1—C4—C5 | 164.1 (2) | C10—C11—C12—C13 | 0.4 (4) |
C2—C1—C4—C9 | −18.2 (4) | C11—C10—C15—C14 | 0.7 (4) |
C2—C3—C10—C11 | 177.5 (3) | C11—C12—C13—C14 | 0.6 (4) |
C2—C3—C10—C15 | −4.0 (4) | C12—C13—C14—C15 | −0.9 (4) |
C3—C10—C11—F1 | −3.8 (3) | C13—C14—C15—C10 | 0.2 (4) |
C3—C10—C11—C12 | 177.6 (2) | C15—C10—C11—F1 | 177.6 (2) |
C3—C10—C15—C14 | −177.8 (2) | C15—C10—C11—C12 | −1.1 (4) |
(2
E)-3-(3-Fluorophenyl)-1-(4-iodophenyl)prop-2-en-1-one (ep2m)
top
Crystal data top
C15H10FIO | Z = 4 |
Mr = 352.13 | F(000) = 680 |
Triclinic, P1 | Dx = 1.815 Mg m−3 |
a = 6.1200 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.7976 (3) Å | Cell parameters from 9911 reflections |
c = 20.3875 (7) Å | θ = 2.4–27.9° |
α = 103.101 (2)° | µ = 2.48 mm−1 |
β = 95.160 (2)° | T = 100 K |
γ = 98.186 (2)° | Block, clear colourless |
V = 1288.32 (7) Å3 | 0.43 × 0.29 × 0.16 mm |
Data collection top
Bruker APEXII Kappa CCD area detector diffractometer | 6172 independent reflections |
Radiation source: fine-focus sealed tube | 5279 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
φ and ω scans | θmax = 28.0°, θmin = 1.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −6→8 |
Tmin = 0.555, Tmax = 0.746 | k = −14→14 |
23620 measured reflections | l = −26→26 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.022 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.051 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0222P)2 + 0.4226P] where P = (Fo2 + 2Fc2)/3 |
6172 reflections | (Δ/σ)max = 0.004 |
325 parameters | Δρmax = 0.92 e Å−3 |
0 restraints | Δρmin = −0.85 e Å−3 |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
I1 | 1.36555 (2) | −0.01728 (2) | 0.63593 (2) | 0.02351 (5) | |
F1 | 0.4599 (2) | 0.67105 (14) | 0.25145 (7) | 0.0307 (3) | |
O1 | 0.6655 (3) | 0.38312 (17) | 0.53627 (9) | 0.0312 (4) | |
C1 | 0.8089 (4) | 0.3402 (2) | 0.50417 (12) | 0.0190 (5) | |
C2 | 0.8480 (4) | 0.3726 (2) | 0.43902 (11) | 0.0179 (4) | |
H2 | 0.960282 | 0.338856 | 0.414639 | 0.021* | |
C3 | 0.7264 (3) | 0.4490 (2) | 0.41422 (11) | 0.0179 (4) | |
H3 | 0.615966 | 0.480071 | 0.440404 | 0.021* | |
C4 | 0.9441 (3) | 0.2544 (2) | 0.53183 (11) | 0.0172 (4) | |
C5 | 0.8831 (4) | 0.2159 (2) | 0.58929 (12) | 0.0215 (5) | |
H5 | 0.756939 | 0.243206 | 0.608501 | 0.026* | |
C6 | 1.0022 (4) | 0.1390 (2) | 0.61890 (12) | 0.0216 (5) | |
H6 | 0.958956 | 0.113591 | 0.658152 | 0.026* | |
C7 | 1.1868 (4) | 0.0991 (2) | 0.59038 (11) | 0.0190 (5) | |
C8 | 1.2509 (4) | 0.1360 (2) | 0.53339 (12) | 0.0212 (5) | |
H8 | 1.377503 | 0.108810 | 0.514451 | 0.025* | |
C9 | 1.1293 (4) | 0.2130 (2) | 0.50399 (11) | 0.0192 (5) | |
H9 | 1.172452 | 0.237853 | 0.464585 | 0.023* | |
C10 | 0.7455 (3) | 0.4897 (2) | 0.35101 (11) | 0.0170 (4) | |
C11 | 0.5933 (4) | 0.5627 (2) | 0.33085 (11) | 0.0184 (4) | |
H11 | 0.481348 | 0.586984 | 0.358183 | 0.022* | |
C12 | 0.6081 (4) | 0.5989 (2) | 0.27056 (11) | 0.0209 (5) | |
C13 | 0.7660 (4) | 0.5665 (2) | 0.22861 (12) | 0.0247 (5) | |
H13 | 0.770657 | 0.591976 | 0.187056 | 0.030* | |
C14 | 0.9179 (4) | 0.4950 (3) | 0.24956 (12) | 0.0276 (5) | |
H14 | 1.030115 | 0.471804 | 0.222103 | 0.033* | |
C15 | 0.9086 (4) | 0.4569 (2) | 0.30975 (12) | 0.0229 (5) | |
H15 | 1.014160 | 0.407912 | 0.323117 | 0.027* | |
I2 | 1.34320 (2) | 1.22178 (2) | 0.27403 (2) | 0.02419 (5) | |
F2 | −0.2840 (2) | 0.90338 (13) | −0.06543 (8) | 0.0326 (3) | |
O2 | 0.6838 (2) | 0.64905 (15) | 0.07814 (8) | 0.0209 (3) | |
C16 | 0.6377 (3) | 0.7580 (2) | 0.08590 (11) | 0.0163 (4) | |
C17 | 0.4295 (3) | 0.7795 (2) | 0.05074 (11) | 0.0179 (4) | |
H17 | 0.389537 | 0.863006 | 0.059915 | 0.021* | |
C18 | 0.2975 (3) | 0.6819 (2) | 0.00618 (11) | 0.0159 (4) | |
H18 | 0.346646 | 0.600844 | −0.001302 | 0.019* | |
C19 | 0.7950 (3) | 0.8707 (2) | 0.13102 (11) | 0.0160 (4) | |
C20 | 0.9986 (3) | 0.8468 (2) | 0.15839 (12) | 0.0192 (5) | |
H20 | 1.030903 | 0.761512 | 0.148211 | 0.023* | |
C21 | 1.1530 (4) | 0.9455 (2) | 0.19995 (12) | 0.0201 (5) | |
H21 | 1.290445 | 0.928546 | 0.218537 | 0.024* | |
C22 | 1.1047 (3) | 1.0695 (2) | 0.21416 (11) | 0.0184 (4) | |
C23 | 0.9043 (4) | 1.0961 (2) | 0.18863 (12) | 0.0218 (5) | |
H23 | 0.872002 | 1.181388 | 0.199581 | 0.026* | |
C24 | 0.7505 (4) | 0.9956 (2) | 0.14655 (12) | 0.0210 (5) | |
H24 | 0.613047 | 1.013014 | 0.128215 | 0.025* | |
C25 | 0.0865 (3) | 0.6851 (2) | −0.03245 (11) | 0.0151 (4) | |
C26 | 0.0024 (4) | 0.7995 (2) | −0.03130 (11) | 0.0192 (5) | |
H26 | 0.084947 | 0.880309 | −0.006366 | 0.023* | |
C27 | −0.2018 (4) | 0.7921 (2) | −0.06701 (12) | 0.0211 (5) | |
C28 | −0.3296 (4) | 0.6781 (2) | −0.10412 (12) | 0.0212 (5) | |
H28 | −0.470738 | 0.677240 | −0.127992 | 0.025* | |
C29 | −0.2463 (4) | 0.5647 (2) | −0.10560 (11) | 0.0196 (5) | |
H29 | −0.330917 | 0.484526 | −0.130658 | 0.024* | |
C30 | −0.0388 (4) | 0.5682 (2) | −0.07041 (11) | 0.0176 (4) | |
H30 | 0.018287 | 0.490306 | −0.072212 | 0.021* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.02484 (8) | 0.02027 (8) | 0.02522 (9) | 0.00525 (6) | −0.00598 (6) | 0.00778 (6) |
F1 | 0.0384 (8) | 0.0314 (8) | 0.0261 (8) | 0.0128 (7) | −0.0025 (6) | 0.0131 (6) |
O1 | 0.0326 (10) | 0.0420 (11) | 0.0330 (10) | 0.0238 (9) | 0.0176 (8) | 0.0219 (9) |
C1 | 0.0180 (11) | 0.0194 (11) | 0.0202 (11) | 0.0026 (9) | 0.0011 (9) | 0.0067 (9) |
C2 | 0.0187 (11) | 0.0178 (11) | 0.0183 (11) | 0.0038 (9) | 0.0047 (9) | 0.0053 (9) |
C3 | 0.0167 (10) | 0.0176 (11) | 0.0194 (11) | 0.0031 (8) | 0.0030 (8) | 0.0042 (9) |
C4 | 0.0166 (10) | 0.0161 (10) | 0.0186 (11) | 0.0026 (8) | 0.0002 (8) | 0.0046 (9) |
C5 | 0.0192 (11) | 0.0257 (12) | 0.0231 (12) | 0.0065 (9) | 0.0045 (9) | 0.0102 (10) |
C6 | 0.0239 (12) | 0.0232 (12) | 0.0194 (11) | 0.0015 (9) | 0.0029 (9) | 0.0099 (10) |
C7 | 0.0208 (11) | 0.0152 (10) | 0.0196 (11) | 0.0027 (9) | −0.0049 (9) | 0.0043 (9) |
C8 | 0.0183 (11) | 0.0243 (12) | 0.0201 (11) | 0.0051 (9) | 0.0023 (9) | 0.0028 (9) |
C9 | 0.0220 (11) | 0.0220 (12) | 0.0149 (11) | 0.0047 (9) | 0.0041 (9) | 0.0060 (9) |
C10 | 0.0188 (11) | 0.0149 (10) | 0.0155 (11) | 0.0002 (8) | −0.0008 (8) | 0.0027 (8) |
C11 | 0.0206 (11) | 0.0161 (11) | 0.0181 (11) | 0.0029 (9) | 0.0022 (9) | 0.0038 (9) |
C12 | 0.0253 (12) | 0.0160 (11) | 0.0190 (11) | 0.0004 (9) | −0.0054 (9) | 0.0047 (9) |
C13 | 0.0317 (13) | 0.0265 (13) | 0.0150 (11) | −0.0015 (10) | 0.0016 (9) | 0.0076 (10) |
C14 | 0.0271 (13) | 0.0366 (14) | 0.0203 (12) | 0.0065 (11) | 0.0082 (10) | 0.0067 (11) |
C15 | 0.0221 (12) | 0.0272 (13) | 0.0219 (12) | 0.0088 (10) | 0.0043 (9) | 0.0079 (10) |
I2 | 0.02082 (8) | 0.01741 (8) | 0.02992 (9) | 0.00249 (6) | −0.00759 (6) | 0.00138 (6) |
F2 | 0.0301 (8) | 0.0217 (7) | 0.0454 (9) | 0.0113 (6) | −0.0086 (7) | 0.0080 (7) |
O2 | 0.0214 (8) | 0.0169 (8) | 0.0238 (8) | 0.0044 (6) | −0.0008 (6) | 0.0044 (7) |
C16 | 0.0157 (10) | 0.0176 (11) | 0.0161 (11) | 0.0031 (8) | 0.0034 (8) | 0.0045 (9) |
C17 | 0.0167 (10) | 0.0172 (11) | 0.0205 (11) | 0.0041 (8) | 0.0012 (8) | 0.0056 (9) |
C18 | 0.0154 (10) | 0.0175 (11) | 0.0162 (10) | 0.0030 (8) | 0.0036 (8) | 0.0060 (9) |
C19 | 0.0147 (10) | 0.0183 (11) | 0.0153 (10) | 0.0032 (8) | 0.0018 (8) | 0.0047 (9) |
C20 | 0.0190 (11) | 0.0166 (11) | 0.0215 (11) | 0.0054 (9) | 0.0007 (9) | 0.0030 (9) |
C21 | 0.0154 (10) | 0.0225 (12) | 0.0235 (12) | 0.0064 (9) | −0.0003 (9) | 0.0069 (10) |
C22 | 0.0168 (10) | 0.0184 (11) | 0.0179 (11) | 0.0005 (8) | −0.0010 (8) | 0.0027 (9) |
C23 | 0.0206 (11) | 0.0163 (11) | 0.0266 (12) | 0.0052 (9) | −0.0019 (9) | 0.0019 (9) |
C24 | 0.0174 (11) | 0.0202 (11) | 0.0246 (12) | 0.0046 (9) | −0.0031 (9) | 0.0049 (10) |
C25 | 0.0150 (10) | 0.0176 (11) | 0.0134 (10) | 0.0023 (8) | 0.0031 (8) | 0.0049 (8) |
C26 | 0.0209 (11) | 0.0156 (11) | 0.0203 (11) | 0.0019 (9) | 0.0007 (9) | 0.0043 (9) |
C27 | 0.0244 (12) | 0.0203 (11) | 0.0222 (12) | 0.0090 (9) | 0.0020 (9) | 0.0095 (9) |
C28 | 0.0162 (10) | 0.0294 (13) | 0.0185 (11) | 0.0032 (9) | 0.0000 (9) | 0.0079 (10) |
C29 | 0.0199 (11) | 0.0201 (11) | 0.0160 (11) | −0.0013 (9) | 0.0012 (9) | 0.0019 (9) |
C30 | 0.0215 (11) | 0.0171 (11) | 0.0145 (10) | 0.0040 (9) | 0.0032 (8) | 0.0039 (9) |
Geometric parameters (Å, º) top
I1—C7 | 2.092 (2) | I2—C22 | 2.100 (2) |
F1—C12 | 1.363 (3) | F2—C27 | 1.363 (2) |
O1—C1 | 1.222 (3) | O2—C16 | 1.228 (3) |
C1—C2 | 1.479 (3) | C16—C17 | 1.479 (3) |
C1—C4 | 1.495 (3) | C16—C19 | 1.501 (3) |
C2—H2 | 0.9500 | C17—H17 | 0.9500 |
C2—C3 | 1.337 (3) | C17—C18 | 1.334 (3) |
C3—H3 | 0.9500 | C18—H18 | 0.9500 |
C3—C10 | 1.462 (3) | C18—C25 | 1.460 (3) |
C4—C5 | 1.393 (3) | C19—C20 | 1.401 (3) |
C4—C9 | 1.397 (3) | C19—C24 | 1.386 (3) |
C5—H5 | 0.9500 | C20—H20 | 0.9500 |
C5—C6 | 1.381 (3) | C20—C21 | 1.381 (3) |
C6—H6 | 0.9500 | C21—H21 | 0.9500 |
C6—C7 | 1.394 (3) | C21—C22 | 1.384 (3) |
C7—C8 | 1.382 (3) | C22—C23 | 1.383 (3) |
C8—H8 | 0.9500 | C23—H23 | 0.9500 |
C8—C9 | 1.388 (3) | C23—C24 | 1.393 (3) |
C9—H9 | 0.9500 | C24—H24 | 0.9500 |
C10—C11 | 1.394 (3) | C25—C26 | 1.400 (3) |
C10—C15 | 1.395 (3) | C25—C30 | 1.399 (3) |
C11—H11 | 0.9500 | C26—H26 | 0.9500 |
C11—C12 | 1.378 (3) | C26—C27 | 1.371 (3) |
C12—C13 | 1.377 (3) | C27—C28 | 1.377 (3) |
C13—H13 | 0.9500 | C28—H28 | 0.9500 |
C13—C14 | 1.387 (3) | C28—C29 | 1.388 (3) |
C14—H14 | 0.9500 | C29—H29 | 0.9500 |
C14—C15 | 1.383 (3) | C29—C30 | 1.393 (3) |
C15—H15 | 0.9500 | C30—H30 | 0.9500 |
| | | |
O1—C1—C2 | 120.6 (2) | O2—C16—C17 | 120.59 (19) |
O1—C1—C4 | 118.9 (2) | O2—C16—C19 | 119.74 (19) |
C2—C1—C4 | 120.5 (2) | C17—C16—C19 | 119.66 (18) |
C1—C2—H2 | 119.8 | C16—C17—H17 | 119.9 |
C3—C2—C1 | 120.4 (2) | C18—C17—C16 | 120.2 (2) |
C3—C2—H2 | 119.8 | C18—C17—H17 | 119.9 |
C2—C3—H3 | 116.6 | C17—C18—H18 | 116.2 |
C2—C3—C10 | 126.8 (2) | C17—C18—C25 | 127.6 (2) |
C10—C3—H3 | 116.6 | C25—C18—H18 | 116.2 |
C5—C4—C1 | 117.7 (2) | C20—C19—C16 | 117.37 (19) |
C5—C4—C9 | 118.7 (2) | C24—C19—C16 | 123.86 (19) |
C9—C4—C1 | 123.6 (2) | C24—C19—C20 | 118.8 (2) |
C4—C5—H5 | 119.4 | C19—C20—H20 | 119.6 |
C6—C5—C4 | 121.3 (2) | C21—C20—C19 | 120.9 (2) |
C6—C5—H5 | 119.4 | C21—C20—H20 | 119.6 |
C5—C6—H6 | 120.5 | C20—C21—H21 | 120.5 |
C5—C6—C7 | 119.1 (2) | C20—C21—C22 | 119.1 (2) |
C7—C6—H6 | 120.5 | C22—C21—H21 | 120.5 |
C6—C7—I1 | 118.55 (17) | C21—C22—I2 | 119.47 (15) |
C8—C7—I1 | 120.68 (17) | C23—C22—I2 | 119.01 (17) |
C8—C7—C6 | 120.8 (2) | C23—C22—C21 | 121.5 (2) |
C7—C8—H8 | 120.2 | C22—C23—H23 | 120.6 |
C7—C8—C9 | 119.6 (2) | C22—C23—C24 | 118.8 (2) |
C9—C8—H8 | 120.2 | C24—C23—H23 | 120.6 |
C4—C9—H9 | 119.7 | C19—C24—C23 | 121.0 (2) |
C8—C9—C4 | 120.6 (2) | C19—C24—H24 | 119.5 |
C8—C9—H9 | 119.7 | C23—C24—H24 | 119.5 |
C11—C10—C3 | 118.7 (2) | C26—C25—C18 | 122.73 (19) |
C11—C10—C15 | 118.9 (2) | C30—C25—C18 | 118.18 (19) |
C15—C10—C3 | 122.4 (2) | C30—C25—C26 | 119.07 (19) |
C10—C11—H11 | 120.6 | C25—C26—H26 | 120.8 |
C12—C11—C10 | 118.8 (2) | C27—C26—C25 | 118.4 (2) |
C12—C11—H11 | 120.6 | C27—C26—H26 | 120.8 |
F1—C12—C11 | 118.5 (2) | F2—C27—C26 | 118.4 (2) |
F1—C12—C13 | 118.1 (2) | F2—C27—C28 | 118.0 (2) |
C13—C12—C11 | 123.4 (2) | C26—C27—C28 | 123.7 (2) |
C12—C13—H13 | 121.4 | C27—C28—H28 | 121.0 |
C12—C13—C14 | 117.2 (2) | C27—C28—C29 | 118.0 (2) |
C14—C13—H13 | 121.4 | C29—C28—H28 | 121.0 |
C13—C14—H14 | 119.5 | C28—C29—H29 | 120.0 |
C15—C14—C13 | 121.1 (2) | C28—C29—C30 | 120.1 (2) |
C15—C14—H14 | 119.5 | C30—C29—H29 | 120.0 |
C10—C15—H15 | 119.7 | C25—C30—H30 | 119.6 |
C14—C15—C10 | 120.6 (2) | C29—C30—C25 | 120.7 (2) |
C14—C15—H15 | 119.7 | C29—C30—H30 | 119.6 |
| | | |
I1—C7—C8—C9 | 179.84 (16) | I2—C22—C23—C24 | 177.27 (17) |
F1—C12—C13—C14 | 178.8 (2) | F2—C27—C28—C29 | −179.8 (2) |
O1—C1—C2—C3 | −0.2 (3) | O2—C16—C17—C18 | −5.1 (3) |
O1—C1—C4—C5 | 7.0 (3) | O2—C16—C19—C20 | 5.0 (3) |
O1—C1—C4—C9 | −171.8 (2) | O2—C16—C19—C24 | −175.4 (2) |
C1—C2—C3—C10 | 179.8 (2) | C16—C17—C18—C25 | 179.4 (2) |
C1—C4—C5—C6 | −178.6 (2) | C16—C19—C20—C21 | 179.5 (2) |
C1—C4—C9—C8 | 178.3 (2) | C16—C19—C24—C23 | −179.7 (2) |
C2—C1—C4—C5 | −173.0 (2) | C17—C16—C19—C20 | −174.6 (2) |
C2—C1—C4—C9 | 8.2 (3) | C17—C16—C19—C24 | 5.1 (3) |
C2—C3—C10—C11 | 175.5 (2) | C17—C18—C25—C26 | 5.7 (4) |
C2—C3—C10—C15 | −3.6 (4) | C17—C18—C25—C30 | −172.4 (2) |
C3—C10—C11—C12 | −178.6 (2) | C18—C25—C26—C27 | −177.3 (2) |
C3—C10—C15—C14 | 178.5 (2) | C18—C25—C30—C29 | 176.9 (2) |
C4—C1—C2—C3 | 179.7 (2) | C19—C16—C17—C18 | 174.4 (2) |
C4—C5—C6—C7 | −0.1 (3) | C19—C20—C21—C22 | −0.3 (3) |
C5—C4—C9—C8 | −0.5 (3) | C20—C19—C24—C23 | −0.1 (3) |
C5—C6—C7—I1 | 179.95 (17) | C20—C21—C22—I2 | −177.51 (17) |
C5—C6—C7—C8 | 0.2 (3) | C20—C21—C22—C23 | 1.1 (4) |
C6—C7—C8—C9 | −0.4 (3) | C21—C22—C23—C24 | −1.4 (4) |
C7—C8—C9—C4 | 0.5 (3) | C22—C23—C24—C19 | 0.8 (4) |
C9—C4—C5—C6 | 0.3 (3) | C24—C19—C20—C21 | −0.2 (3) |
C10—C11—C12—F1 | −179.47 (19) | C25—C26—C27—F2 | 179.53 (19) |
C10—C11—C12—C13 | 0.2 (3) | C25—C26—C27—C28 | 0.0 (4) |
C11—C10—C15—C14 | −0.6 (3) | C26—C25—C30—C29 | −1.2 (3) |
C11—C12—C13—C14 | −0.8 (3) | C26—C27—C28—C29 | −0.3 (4) |
C12—C13—C14—C15 | 0.7 (4) | C27—C28—C29—C30 | −0.2 (3) |
C13—C14—C15—C10 | −0.1 (4) | C28—C29—C30—C25 | 1.0 (3) |
C15—C10—C11—C12 | 0.5 (3) | C30—C25—C26—C27 | 0.8 (3) |
(2
E)-1-(4-Iodophenyl)-3-(4-nitrophenyl)prop-2-en-1-one (ep8p)
top
Crystal data top
C15H10INO3 | F(000) = 1472 |
Mr = 379.14 | Dx = 1.882 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 17.9016 (7) Å | Cell parameters from 8739 reflections |
b = 5.8824 (2) Å | θ = 2.3–29.6° |
c = 25.4871 (9) Å | µ = 2.40 mm−1 |
β = 94.427 (2)° | T = 100 K |
V = 2675.89 (17) Å3 | Plate, clear yellow |
Z = 8 | 0.47 × 0.19 × 0.08 mm |
Data collection top
Bruker APEXII Kappa CCD area detector diffractometer | 6154 independent reflections |
Radiation source: fine-focus sealed tube | 4831 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.051 |
φ and ω scans | θmax = 27.5°, θmin = 1.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −23→23 |
Tmin = 0.581, Tmax = 0.746 | k = −7→7 |
36371 measured reflections | l = −33→33 |
Refinement top
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.072 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0251P)2 + 3.8267P] where P = (Fo2 + 2Fc2)/3 |
6154 reflections | (Δ/σ)max = 0.003 |
361 parameters | Δρmax = 0.92 e Å−3 |
0 restraints | Δρmin = −0.80 e Å−3 |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
I1 | 0.46827 (2) | 0.18749 (4) | 0.89263 (2) | 0.02620 (7) | |
O1 | 0.68944 (14) | 0.6988 (4) | 0.70781 (9) | 0.0251 (5) | |
N1 | 0.87643 (15) | −0.1862 (5) | 0.48753 (11) | 0.0190 (6) | |
C1 | 0.67394 (18) | 0.4972 (5) | 0.71254 (13) | 0.0188 (7) | |
O2 | 0.92791 (17) | −0.1047 (5) | 0.46719 (13) | 0.0473 (8) | |
C2 | 0.70117 (18) | 0.3212 (6) | 0.67699 (13) | 0.0214 (7) | |
H2 | 0.683258 | 0.169560 | 0.678692 | 0.026* | |
O3 | 0.84712 (15) | −0.3676 (4) | 0.47756 (10) | 0.0300 (6) | |
C3 | 0.75063 (18) | 0.3755 (5) | 0.64273 (13) | 0.0182 (7) | |
H3 | 0.768137 | 0.528013 | 0.643582 | 0.022* | |
C4 | 0.62526 (18) | 0.4217 (5) | 0.75461 (13) | 0.0192 (7) | |
C5 | 0.57507 (19) | 0.5762 (5) | 0.77384 (13) | 0.0204 (7) | |
H5 | 0.571666 | 0.725556 | 0.759655 | 0.024* | |
C6 | 0.53000 (19) | 0.5148 (6) | 0.81344 (14) | 0.0227 (7) | |
H6 | 0.495138 | 0.619972 | 0.825837 | 0.027* | |
C7 | 0.53647 (18) | 0.2985 (6) | 0.83465 (13) | 0.0200 (7) | |
C8 | 0.58707 (19) | 0.1446 (6) | 0.81632 (14) | 0.0218 (7) | |
H8 | 0.591796 | −0.002557 | 0.831562 | 0.026* | |
C9 | 0.63056 (18) | 0.2040 (5) | 0.77610 (13) | 0.0208 (7) | |
H9 | 0.664132 | 0.096509 | 0.763057 | 0.025* | |
C10 | 0.78105 (17) | 0.2247 (5) | 0.60376 (12) | 0.0175 (7) | |
C11 | 0.84278 (18) | 0.2979 (5) | 0.57823 (13) | 0.0189 (7) | |
H11 | 0.863488 | 0.443370 | 0.586549 | 0.023* | |
C12 | 0.87495 (18) | 0.1652 (6) | 0.54110 (13) | 0.0213 (7) | |
H12 | 0.917650 | 0.216121 | 0.524519 | 0.026* | |
C13 | 0.84279 (18) | −0.0432 (5) | 0.52907 (13) | 0.0181 (6) | |
C14 | 0.78134 (19) | −0.1245 (5) | 0.55299 (13) | 0.0193 (7) | |
H14 | 0.760577 | −0.269151 | 0.543857 | 0.023* | |
C15 | 0.75071 (18) | 0.0098 (5) | 0.59061 (13) | 0.0197 (7) | |
H15 | 0.708800 | −0.044026 | 0.607671 | 0.024* | |
I2 | 1.03760 (2) | 0.56634 (4) | 0.61108 (2) | 0.02643 (7) | |
N2 | 0.61577 (15) | 0.1927 (5) | 1.01386 (11) | 0.0214 (6) | |
O4 | 0.80218 (13) | 1.0460 (4) | 0.78924 (9) | 0.0234 (5) | |
O5 | 0.56272 (16) | 0.2723 (5) | 1.03340 (12) | 0.0398 (7) | |
O6 | 0.64466 (14) | 0.0096 (4) | 1.02509 (10) | 0.0278 (6) | |
C16 | 0.81836 (17) | 0.8438 (5) | 0.78593 (13) | 0.0181 (7) | |
C17 | 0.79033 (18) | 0.6748 (6) | 0.82274 (13) | 0.0204 (7) | |
H17 | 0.804312 | 0.519674 | 0.820070 | 0.024* | |
C18 | 0.74621 (18) | 0.7376 (5) | 0.85914 (13) | 0.0191 (7) | |
H18 | 0.733938 | 0.894580 | 0.860184 | 0.023* | |
C19 | 0.86846 (17) | 0.7688 (5) | 0.74496 (13) | 0.0167 (6) | |
C20 | 0.88392 (18) | 0.9224 (5) | 0.70561 (13) | 0.0201 (7) | |
H20 | 0.860891 | 1.067966 | 0.704996 | 0.024* | |
C21 | 0.93160 (18) | 0.8689 (5) | 0.66763 (13) | 0.0201 (7) | |
H21 | 0.941017 | 0.975305 | 0.640879 | 0.024* | |
C22 | 0.96584 (18) | 0.6563 (6) | 0.66908 (13) | 0.0198 (7) | |
C23 | 0.95161 (18) | 0.4993 (5) | 0.70757 (13) | 0.0203 (7) | |
H23 | 0.975137 | 0.354460 | 0.708091 | 0.024* | |
C24 | 0.90279 (18) | 0.5546 (5) | 0.74538 (13) | 0.0200 (7) | |
H24 | 0.892625 | 0.446785 | 0.771652 | 0.024* | |
C25 | 0.71394 (18) | 0.5920 (5) | 0.89822 (13) | 0.0189 (7) | |
C26 | 0.65261 (18) | 0.6727 (6) | 0.92375 (13) | 0.0198 (7) | |
H26 | 0.633272 | 0.819774 | 0.915379 | 0.024* | |
C27 | 0.61967 (18) | 0.5430 (5) | 0.96082 (13) | 0.0198 (7) | |
H27 | 0.577232 | 0.596784 | 0.977279 | 0.024* | |
C28 | 0.65047 (17) | 0.3322 (5) | 0.97321 (13) | 0.0179 (6) | |
C29 | 0.71203 (18) | 0.2460 (5) | 0.94951 (13) | 0.0189 (7) | |
H29 | 0.732223 | 0.101136 | 0.959070 | 0.023* | |
C30 | 0.74283 (18) | 0.3765 (5) | 0.91181 (13) | 0.0198 (7) | |
H30 | 0.784307 | 0.319533 | 0.894746 | 0.024* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.02316 (12) | 0.03385 (13) | 0.02215 (12) | −0.00656 (10) | 0.00543 (9) | −0.00175 (10) |
O1 | 0.0314 (13) | 0.0209 (12) | 0.0238 (13) | −0.0031 (10) | 0.0064 (11) | −0.0010 (10) |
N1 | 0.0187 (13) | 0.0190 (14) | 0.0192 (14) | −0.0050 (12) | 0.0007 (11) | 0.0050 (11) |
C1 | 0.0196 (16) | 0.0191 (16) | 0.0178 (16) | 0.0026 (13) | 0.0013 (13) | −0.0005 (13) |
O2 | 0.0505 (18) | 0.0415 (17) | 0.054 (2) | −0.0123 (14) | 0.0310 (16) | −0.0199 (15) |
C2 | 0.0240 (17) | 0.0175 (16) | 0.0225 (17) | 0.0001 (14) | 0.0007 (14) | 0.0000 (14) |
O3 | 0.0374 (15) | 0.0239 (13) | 0.0297 (14) | −0.0004 (11) | 0.0094 (12) | −0.0033 (11) |
C3 | 0.0208 (16) | 0.0158 (15) | 0.0179 (16) | 0.0005 (12) | 0.0013 (13) | −0.0002 (12) |
C4 | 0.0204 (16) | 0.0193 (16) | 0.0173 (16) | −0.0008 (13) | −0.0016 (13) | −0.0018 (13) |
C5 | 0.0260 (17) | 0.0141 (15) | 0.0208 (17) | 0.0026 (13) | 0.0003 (14) | −0.0018 (13) |
C6 | 0.0203 (17) | 0.0218 (17) | 0.0257 (18) | 0.0033 (13) | 0.0003 (14) | −0.0030 (14) |
C7 | 0.0201 (16) | 0.0217 (16) | 0.0184 (16) | −0.0044 (14) | 0.0021 (13) | −0.0005 (13) |
C8 | 0.0235 (17) | 0.0189 (16) | 0.0225 (17) | −0.0007 (13) | −0.0008 (14) | 0.0036 (13) |
C9 | 0.0195 (16) | 0.0168 (16) | 0.0263 (18) | 0.0060 (13) | 0.0035 (14) | −0.0037 (14) |
C10 | 0.0178 (16) | 0.0193 (15) | 0.0154 (16) | 0.0016 (13) | 0.0016 (13) | 0.0041 (13) |
C11 | 0.0215 (16) | 0.0152 (15) | 0.0199 (16) | −0.0009 (13) | 0.0012 (13) | 0.0020 (13) |
C12 | 0.0188 (16) | 0.0228 (17) | 0.0228 (17) | −0.0014 (14) | 0.0053 (14) | 0.0025 (14) |
C13 | 0.0196 (16) | 0.0172 (15) | 0.0173 (16) | 0.0057 (13) | 0.0007 (13) | 0.0015 (13) |
C14 | 0.0238 (17) | 0.0149 (15) | 0.0189 (17) | −0.0015 (13) | −0.0005 (14) | 0.0024 (12) |
C15 | 0.0199 (16) | 0.0179 (16) | 0.0212 (17) | 0.0000 (13) | 0.0017 (14) | 0.0015 (13) |
I2 | 0.02098 (12) | 0.03531 (14) | 0.02379 (12) | −0.00022 (10) | 0.00677 (9) | −0.00353 (10) |
N2 | 0.0216 (14) | 0.0216 (14) | 0.0204 (15) | 0.0047 (12) | −0.0014 (12) | −0.0072 (12) |
O4 | 0.0257 (13) | 0.0186 (12) | 0.0264 (13) | 0.0016 (10) | 0.0059 (10) | 0.0014 (10) |
O5 | 0.0422 (16) | 0.0365 (15) | 0.0446 (17) | 0.0118 (13) | 0.0279 (14) | 0.0095 (13) |
O6 | 0.0344 (14) | 0.0192 (12) | 0.0309 (14) | 0.0012 (11) | 0.0100 (12) | 0.0044 (10) |
C16 | 0.0168 (15) | 0.0177 (16) | 0.0194 (16) | −0.0014 (13) | −0.0019 (13) | 0.0021 (13) |
C17 | 0.0202 (16) | 0.0186 (16) | 0.0225 (17) | −0.0013 (14) | 0.0024 (14) | 0.0007 (13) |
C18 | 0.0200 (16) | 0.0171 (16) | 0.0200 (17) | −0.0012 (13) | 0.0005 (13) | −0.0017 (13) |
C19 | 0.0159 (15) | 0.0155 (15) | 0.0188 (16) | −0.0028 (12) | 0.0011 (13) | 0.0002 (12) |
C20 | 0.0225 (17) | 0.0154 (15) | 0.0216 (17) | 0.0040 (13) | −0.0026 (14) | 0.0017 (13) |
C21 | 0.0217 (17) | 0.0190 (16) | 0.0196 (17) | −0.0005 (13) | 0.0005 (14) | 0.0037 (13) |
C22 | 0.0179 (16) | 0.0218 (16) | 0.0199 (17) | −0.0032 (13) | 0.0028 (13) | −0.0036 (13) |
C23 | 0.0199 (16) | 0.0142 (15) | 0.0267 (18) | 0.0027 (12) | 0.0015 (14) | −0.0031 (13) |
C24 | 0.0182 (16) | 0.0181 (16) | 0.0240 (17) | 0.0000 (13) | 0.0041 (13) | 0.0043 (13) |
C25 | 0.0199 (16) | 0.0186 (16) | 0.0180 (16) | −0.0026 (13) | 0.0011 (13) | −0.0033 (13) |
C26 | 0.0242 (17) | 0.0173 (15) | 0.0181 (16) | 0.0031 (14) | 0.0023 (13) | −0.0021 (13) |
C27 | 0.0210 (16) | 0.0195 (16) | 0.0193 (16) | 0.0019 (13) | 0.0037 (13) | −0.0041 (13) |
C28 | 0.0177 (15) | 0.0207 (16) | 0.0156 (15) | −0.0006 (13) | 0.0030 (13) | −0.0028 (13) |
C29 | 0.0193 (16) | 0.0165 (15) | 0.0209 (17) | 0.0024 (13) | 0.0015 (13) | −0.0014 (13) |
C30 | 0.0187 (16) | 0.0197 (16) | 0.0212 (17) | 0.0021 (13) | 0.0039 (14) | −0.0026 (13) |
Geometric parameters (Å, º) top
I1—C7 | 2.093 (3) | I2—C22 | 2.100 (3) |
O1—C1 | 1.226 (4) | N2—O5 | 1.201 (4) |
N1—O2 | 1.192 (4) | N2—O6 | 1.219 (3) |
N1—O3 | 1.207 (3) | N2—C28 | 1.494 (4) |
N1—C13 | 1.513 (4) | O4—C16 | 1.229 (4) |
C1—C2 | 1.483 (5) | C16—C17 | 1.481 (4) |
C1—C4 | 1.500 (5) | C16—C19 | 1.495 (5) |
C2—H2 | 0.9500 | C17—H17 | 0.9500 |
C2—C3 | 1.330 (5) | C17—C18 | 1.317 (5) |
C3—H3 | 0.9500 | C18—H18 | 0.9500 |
C3—C10 | 1.467 (4) | C18—C25 | 1.466 (5) |
C4—C5 | 1.394 (4) | C19—C20 | 1.393 (4) |
C4—C9 | 1.393 (4) | C19—C24 | 1.402 (4) |
C5—H5 | 0.9500 | C20—H20 | 0.9500 |
C5—C6 | 1.388 (5) | C20—C21 | 1.376 (5) |
C6—H6 | 0.9500 | C21—H21 | 0.9500 |
C6—C7 | 1.384 (5) | C21—C22 | 1.392 (4) |
C7—C8 | 1.387 (5) | C22—C23 | 1.385 (5) |
C8—H8 | 0.9500 | C23—H23 | 0.9500 |
C8—C9 | 1.379 (5) | C23—C24 | 1.389 (5) |
C9—H9 | 0.9500 | C24—H24 | 0.9500 |
C10—C11 | 1.393 (4) | C25—C26 | 1.402 (4) |
C10—C15 | 1.406 (4) | C25—C30 | 1.403 (4) |
C11—H11 | 0.9500 | C26—H26 | 0.9500 |
C11—C12 | 1.386 (5) | C26—C27 | 1.382 (5) |
C12—H12 | 0.9500 | C27—H27 | 0.9500 |
C12—C13 | 1.379 (5) | C27—C28 | 1.383 (4) |
C13—C14 | 1.384 (5) | C28—C29 | 1.393 (4) |
C14—H14 | 0.9500 | C29—H29 | 0.9500 |
C14—C15 | 1.388 (5) | C29—C30 | 1.378 (5) |
C15—H15 | 0.9500 | C30—H30 | 0.9500 |
| | | |
O2—N1—O3 | 127.0 (3) | O5—N2—O6 | 125.6 (3) |
O2—N1—C13 | 116.3 (3) | O5—N2—C28 | 117.3 (3) |
O3—N1—C13 | 116.7 (3) | O6—N2—C28 | 117.2 (3) |
O1—C1—C2 | 121.8 (3) | O4—C16—C17 | 120.9 (3) |
O1—C1—C4 | 120.3 (3) | O4—C16—C19 | 119.4 (3) |
C2—C1—C4 | 117.8 (3) | C17—C16—C19 | 119.7 (3) |
C1—C2—H2 | 120.0 | C16—C17—H17 | 119.7 |
C3—C2—C1 | 120.0 (3) | C18—C17—C16 | 120.6 (3) |
C3—C2—H2 | 120.0 | C18—C17—H17 | 119.7 |
C2—C3—H3 | 116.6 | C17—C18—H18 | 116.4 |
C2—C3—C10 | 126.9 (3) | C17—C18—C25 | 127.2 (3) |
C10—C3—H3 | 116.6 | C25—C18—H18 | 116.4 |
C5—C4—C1 | 118.9 (3) | C20—C19—C16 | 118.3 (3) |
C9—C4—C1 | 121.8 (3) | C20—C19—C24 | 118.5 (3) |
C9—C4—C5 | 119.2 (3) | C24—C19—C16 | 123.1 (3) |
C4—C5—H5 | 119.6 | C19—C20—H20 | 119.1 |
C6—C5—C4 | 120.8 (3) | C21—C20—C19 | 121.8 (3) |
C6—C5—H5 | 119.6 | C21—C20—H20 | 119.1 |
C5—C6—H6 | 120.4 | C20—C21—H21 | 120.6 |
C7—C6—C5 | 119.2 (3) | C20—C21—C22 | 118.8 (3) |
C7—C6—H6 | 120.4 | C22—C21—H21 | 120.6 |
C6—C7—I1 | 121.8 (2) | C21—C22—I2 | 120.0 (2) |
C6—C7—C8 | 120.4 (3) | C23—C22—I2 | 119.1 (2) |
C8—C7—I1 | 117.8 (2) | C23—C22—C21 | 120.9 (3) |
C7—C8—H8 | 119.8 | C22—C23—H23 | 120.2 |
C9—C8—C7 | 120.4 (3) | C22—C23—C24 | 119.7 (3) |
C9—C8—H8 | 119.8 | C24—C23—H23 | 120.2 |
C4—C9—H9 | 120.0 | C19—C24—H24 | 119.9 |
C8—C9—C4 | 120.0 (3) | C23—C24—C19 | 120.3 (3) |
C8—C9—H9 | 120.0 | C23—C24—H24 | 119.9 |
C11—C10—C3 | 118.6 (3) | C26—C25—C18 | 118.8 (3) |
C11—C10—C15 | 118.2 (3) | C26—C25—C30 | 118.6 (3) |
C15—C10—C3 | 123.2 (3) | C30—C25—C18 | 122.6 (3) |
C10—C11—H11 | 118.9 | C25—C26—H26 | 119.3 |
C12—C11—C10 | 122.1 (3) | C27—C26—C25 | 121.4 (3) |
C12—C11—H11 | 118.9 | C27—C26—H26 | 119.3 |
C11—C12—H12 | 121.2 | C26—C27—H27 | 121.1 |
C13—C12—C11 | 117.7 (3) | C26—C27—C28 | 117.9 (3) |
C13—C12—H12 | 121.2 | C28—C27—H27 | 121.1 |
C12—C13—N1 | 117.9 (3) | C27—C28—N2 | 118.1 (3) |
C12—C13—C14 | 122.8 (3) | C27—C28—C29 | 122.8 (3) |
C14—C13—N1 | 119.3 (3) | C29—C28—N2 | 119.1 (3) |
C13—C14—H14 | 120.7 | C28—C29—H29 | 120.9 |
C13—C14—C15 | 118.5 (3) | C30—C29—C28 | 118.2 (3) |
C15—C14—H14 | 120.7 | C30—C29—H29 | 120.9 |
C10—C15—H15 | 119.6 | C25—C30—H30 | 119.5 |
C14—C15—C10 | 120.7 (3) | C29—C30—C25 | 121.1 (3) |
C14—C15—H15 | 119.6 | C29—C30—H30 | 119.5 |
| | | |
I1—C7—C8—C9 | 176.4 (3) | I2—C22—C23—C24 | −178.4 (2) |
O1—C1—C2—C3 | 7.9 (5) | N2—C28—C29—C30 | 179.5 (3) |
O1—C1—C4—C5 | 25.1 (5) | O4—C16—C17—C18 | 1.4 (5) |
O1—C1—C4—C9 | −152.8 (3) | O4—C16—C19—C20 | −11.8 (5) |
N1—C13—C14—C15 | −179.3 (3) | O4—C16—C19—C24 | 165.7 (3) |
C1—C2—C3—C10 | −177.7 (3) | O5—N2—C28—C27 | 0.2 (4) |
C1—C4—C5—C6 | −178.8 (3) | O5—N2—C28—C29 | −179.9 (3) |
C1—C4—C9—C8 | 177.2 (3) | O6—N2—C28—C27 | −178.5 (3) |
O2—N1—C13—C12 | −1.6 (4) | O6—N2—C28—C29 | 1.5 (4) |
O2—N1—C13—C14 | 177.9 (3) | C16—C17—C18—C25 | 179.9 (3) |
C2—C1—C4—C5 | −154.0 (3) | C16—C19—C20—C21 | 177.6 (3) |
C2—C1—C4—C9 | 28.0 (5) | C16—C19—C24—C23 | −176.9 (3) |
C2—C3—C10—C11 | −167.7 (3) | C17—C16—C19—C20 | 169.6 (3) |
C2—C3—C10—C15 | 12.6 (5) | C17—C16—C19—C24 | −12.9 (5) |
O3—N1—C13—C12 | −179.7 (3) | C17—C18—C25—C26 | −162.2 (3) |
O3—N1—C13—C14 | −0.2 (4) | C17—C18—C25—C30 | 18.9 (5) |
C3—C10—C11—C12 | 179.7 (3) | C18—C25—C26—C27 | 179.8 (3) |
C3—C10—C15—C14 | 179.3 (3) | C18—C25—C30—C29 | 178.7 (3) |
C4—C1—C2—C3 | −173.0 (3) | C19—C16—C17—C18 | 179.9 (3) |
C4—C5—C6—C7 | 1.4 (5) | C19—C20—C21—C22 | −0.7 (5) |
C5—C4—C9—C8 | −0.7 (5) | C20—C19—C24—C23 | 0.6 (5) |
C5—C6—C7—I1 | −177.9 (2) | C20—C21—C22—I2 | 179.0 (2) |
C5—C6—C7—C8 | −0.4 (5) | C20—C21—C22—C23 | 0.8 (5) |
C6—C7—C8—C9 | −1.2 (5) | C21—C22—C23—C24 | −0.2 (5) |
C7—C8—C9—C4 | 1.7 (5) | C22—C23—C24—C19 | −0.5 (5) |
C9—C4—C5—C6 | −0.8 (5) | C24—C19—C20—C21 | 0.0 (5) |
C10—C11—C12—C13 | 1.3 (5) | C25—C26—C27—C28 | 1.8 (5) |
C11—C10—C15—C14 | −0.4 (5) | C26—C25—C30—C29 | −0.2 (5) |
C11—C12—C13—N1 | 178.4 (3) | C26—C27—C28—N2 | 179.1 (3) |
C11—C12—C13—C14 | −1.0 (5) | C26—C27—C28—C29 | −0.8 (5) |
C12—C13—C14—C15 | 0.1 (5) | C27—C28—C29—C30 | −0.6 (5) |
C13—C14—C15—C10 | 0.6 (5) | C28—C29—C30—C25 | 1.1 (5) |
C15—C10—C11—C12 | −0.6 (5) | C30—C25—C26—C27 | −1.3 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9···O4i | 0.95 | 2.53 | 3.202 (4) | 128 |
C14—H14···O6ii | 0.95 | 2.53 | 3.370 (4) | 148 |
C29—H29···O3iii | 0.95 | 2.49 | 3.324 (4) | 147 |
Symmetry codes: (i) x, y−1, z; (ii) x, −y−1/2, z−1/2; (iii) x, −y−1/2, z+1/2. |