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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...O2N 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520621002961/bm5139sup1.cif
Contains datablocks ep2o, ep2m, ep8p

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520621002961/bm5139ep2osup2.hkl
Contains datablock ep2o

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520621002961/bm5139ep2msup3.hkl
Contains datablock ep2m

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520621002961/bm5139ep8psup4.hkl
Contains datablock ep8p

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520621002961/bm5139sup5.pdf
Addition information

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2052520621002961/bm5139ep2osup6.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2052520621002961/bm5139ep2msup7.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2052520621002961/bm5139ep8psup8.cml
Supplementary material

CCDC references: 2050700; 2050701; 2050702

Computing details top

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).

(2E)-3-(2-Fluorophenyl)-1-(4-iodophenyl)prop-2-en-1-one (ep2o) top
Crystal data top
C15H10FIOF(000) = 680
Mr = 352.13Dx = 1.769 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 22.9802 (10) ÅCell parameters from 4157 reflections
b = 4.7448 (2) Åθ = 2.7–27.8°
c = 12.2026 (6) ŵ = 2.42 mm1
β = 96.534 (2)°T = 100 K
V = 1321.89 (10) Å3Block, clear colourless
Z = 40.48 × 0.28 × 0.18 mm
Data collection top
Bruker APEXII Kappa CCD area detector
diffractometer
3019 independent reflections
Radiation source: fine-focus sealed tube2628 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
φ and ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
h = 2929
Tmin = 0.606, Tmax = 0.746k = 66
10963 measured reflectionsl = 815
Refinement top
Refinement on F2Primary atom site location: iterative
Least-squares matrix: fullSecondary atom site location: diffmap
R[F2 > 2σ(F2)] = 0.024Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.057H-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 parametersΔρmax = 0.66 e Å3
0 restraintsΔρmin = 0.52 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.95514 (2)0.08114 (4)0.32982 (2)0.02230 (7)
F10.57442 (7)1.4067 (3)0.52807 (12)0.0303 (4)
O10.74598 (9)0.8128 (5)0.60332 (14)0.0330 (5)
C10.75618 (11)0.8393 (6)0.5071 (2)0.0214 (5)
C20.72235 (11)1.0410 (5)0.4316 (2)0.0203 (5)
H20.7344521.0751800.3609200.024*
C30.67557 (11)1.1752 (5)0.46031 (19)0.0202 (5)
H30.6640831.1336010.5309010.024*
C40.80339 (11)0.6695 (5)0.46366 (19)0.0188 (5)
C50.84511 (12)0.5329 (6)0.5388 (2)0.0235 (6)
H50.8436740.5560980.6157600.028*
C60.88826 (12)0.3649 (6)0.5021 (2)0.0236 (6)
H60.9164310.2744720.5533480.028*
C70.88983 (11)0.3304 (5)0.38914 (19)0.0187 (5)
C80.84888 (11)0.4611 (5)0.3131 (2)0.0205 (5)
H80.8499210.4331930.2362820.025*
C90.80618 (11)0.6337 (5)0.35095 (19)0.0199 (5)
H90.7787590.7278330.2993590.024*
C100.64031 (11)1.3807 (5)0.39290 (19)0.0183 (5)
C110.59061 (11)1.5000 (6)0.4304 (2)0.0208 (5)
C120.55626 (11)1.7033 (6)0.3732 (2)0.0250 (6)
H120.5229721.7789460.4023570.030*
C130.57147 (12)1.7939 (6)0.2726 (2)0.0260 (6)
H130.5488371.9346270.2320410.031*
C140.62004 (12)1.6782 (6)0.2310 (2)0.0246 (6)
H140.6300731.7387650.1613240.029*
C150.65387 (11)1.4765 (5)0.2896 (2)0.0207 (5)
H150.6869311.4008270.2596770.025*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.02079 (10)0.02608 (10)0.02034 (10)0.00181 (7)0.00365 (6)0.00239 (7)
F10.0324 (9)0.0377 (10)0.0228 (8)0.0026 (7)0.0118 (6)0.0023 (7)
O10.0399 (12)0.0464 (13)0.0130 (9)0.0138 (10)0.0048 (8)0.0026 (9)
C10.0244 (13)0.0233 (13)0.0159 (12)0.0018 (10)0.0006 (10)0.0015 (10)
C20.0265 (13)0.0203 (13)0.0143 (11)0.0019 (11)0.0038 (10)0.0002 (10)
C30.0244 (13)0.0230 (13)0.0129 (11)0.0034 (10)0.0013 (9)0.0013 (10)
C40.0209 (13)0.0204 (12)0.0151 (11)0.0032 (10)0.0015 (9)0.0015 (10)
C50.0294 (14)0.0277 (14)0.0129 (11)0.0022 (12)0.0009 (10)0.0005 (10)
C60.0269 (14)0.0263 (14)0.0166 (12)0.0022 (11)0.0020 (10)0.0040 (10)
C70.0203 (12)0.0191 (12)0.0168 (12)0.0004 (10)0.0022 (9)0.0003 (10)
C80.0236 (13)0.0248 (14)0.0134 (11)0.0010 (11)0.0028 (9)0.0010 (10)
C90.0230 (13)0.0221 (13)0.0138 (11)0.0005 (10)0.0009 (9)0.0035 (9)
C100.0188 (12)0.0189 (12)0.0168 (12)0.0029 (10)0.0000 (9)0.0033 (9)
C110.0234 (13)0.0226 (13)0.0170 (11)0.0065 (10)0.0050 (10)0.0046 (10)
C120.0182 (12)0.0259 (14)0.0311 (14)0.0002 (11)0.0040 (10)0.0073 (12)
C130.0262 (14)0.0239 (14)0.0259 (13)0.0019 (12)0.0050 (10)0.0014 (11)
C140.0301 (15)0.0246 (14)0.0187 (12)0.0002 (11)0.0016 (10)0.0001 (11)
C150.0217 (13)0.0228 (13)0.0181 (12)0.0012 (10)0.0039 (10)0.0018 (10)
Geometric parameters (Å, º) top
I1—C72.103 (2)C7—C81.390 (3)
F1—C111.362 (3)C8—H80.9500
O1—C11.230 (3)C8—C91.396 (4)
C1—C21.485 (4)C9—H90.9500
C1—C41.496 (4)C10—C111.398 (3)
C2—H20.9500C10—C151.408 (3)
C2—C31.330 (4)C11—C121.384 (4)
C3—H30.9500C12—H120.9500
C3—C101.460 (3)C12—C131.383 (4)
C4—C51.407 (4)C13—H130.9500
C4—C91.395 (3)C13—C141.391 (4)
C5—H50.9500C14—H140.9500
C5—C61.386 (4)C14—C151.381 (4)
C6—H60.9500C15—H150.9500
C6—C71.392 (3)
O1—C1—C2121.0 (2)C9—C8—H8120.4
O1—C1—C4120.5 (2)C4—C9—C8120.7 (2)
C2—C1—C4118.5 (2)C4—C9—H9119.7
C1—C2—H2119.1C8—C9—H9119.7
C3—C2—C1121.8 (2)C11—C10—C3120.5 (2)
C3—C2—H2119.1C11—C10—C15115.8 (2)
C2—C3—H3117.1C15—C10—C3123.7 (2)
C2—C3—C10125.8 (2)F1—C11—C10118.0 (2)
C10—C3—H3117.1F1—C11—C12118.1 (2)
C5—C4—C1119.0 (2)C12—C11—C10123.9 (2)
C9—C4—C1122.1 (2)C11—C12—H12120.7
C9—C4—C5118.8 (2)C13—C12—C11118.5 (2)
C4—C5—H5119.5C13—C12—H12120.7
C6—C5—C4120.9 (2)C12—C13—H13120.1
C6—C5—H5119.5C12—C13—C14119.7 (2)
C5—C6—H6120.4C14—C13—H13120.1
C5—C6—C7119.2 (2)C13—C14—H14119.6
C7—C6—H6120.4C15—C14—C13120.8 (2)
C6—C7—I1120.45 (18)C15—C14—H14119.6
C8—C7—I1118.47 (17)C10—C15—H15119.4
C8—C7—C6121.1 (2)C14—C15—C10121.3 (2)
C7—C8—H8120.4C14—C15—H15119.4
C7—C8—C9119.3 (2)
I1—C7—C8—C9178.22 (18)C4—C1—C2—C3172.2 (2)
F1—C11—C12—C13178.3 (2)C4—C5—C6—C70.4 (4)
O1—C1—C2—C38.1 (4)C5—C4—C9—C81.3 (4)
O1—C1—C4—C515.5 (4)C5—C6—C7—I1179.3 (2)
O1—C1—C4—C9162.2 (2)C5—C6—C7—C80.1 (4)
C1—C2—C3—C10178.7 (2)C6—C7—C8—C91.2 (4)
C1—C4—C5—C6177.6 (2)C7—C8—C9—C41.8 (4)
C1—C4—C9—C8176.4 (2)C9—C4—C5—C60.2 (4)
C2—C1—C4—C5164.1 (2)C10—C11—C12—C130.4 (4)
C2—C1—C4—C918.2 (4)C11—C10—C15—C140.7 (4)
C2—C3—C10—C11177.5 (3)C11—C12—C13—C140.6 (4)
C2—C3—C10—C154.0 (4)C12—C13—C14—C150.9 (4)
C3—C10—C11—F13.8 (3)C13—C14—C15—C100.2 (4)
C3—C10—C11—C12177.6 (2)C15—C10—C11—F1177.6 (2)
C3—C10—C15—C14177.8 (2)C15—C10—C11—C121.1 (4)
(2E)-3-(3-Fluorophenyl)-1-(4-iodophenyl)prop-2-en-1-one (ep2m) top
Crystal data top
C15H10FIOZ = 4
Mr = 352.13F(000) = 680
Triclinic, P1Dx = 1.815 Mg m3
a = 6.1200 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.7976 (3) ÅCell parameters from 9911 reflections
c = 20.3875 (7) Åθ = 2.4–27.9°
α = 103.101 (2)°µ = 2.48 mm1
β = 95.160 (2)°T = 100 K
γ = 98.186 (2)°Block, clear colourless
V = 1288.32 (7) Å30.43 × 0.29 × 0.16 mm
Data collection top
Bruker APEXII Kappa CCD area detector
diffractometer
6172 independent reflections
Radiation source: fine-focus sealed tube5279 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
φ and ω scansθmax = 28.0°, θmin = 1.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
h = 68
Tmin = 0.555, Tmax = 0.746k = 1414
23620 measured reflectionsl = 2626
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.022Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.051H-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 parametersΔρmax = 0.92 e Å3
0 restraintsΔρmin = 0.85 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I11.36555 (2)0.01728 (2)0.63593 (2)0.02351 (5)
F10.4599 (2)0.67105 (14)0.25145 (7)0.0307 (3)
O10.6655 (3)0.38312 (17)0.53627 (9)0.0312 (4)
C10.8089 (4)0.3402 (2)0.50417 (12)0.0190 (5)
C20.8480 (4)0.3726 (2)0.43902 (11)0.0179 (4)
H20.9602820.3388560.4146390.021*
C30.7264 (3)0.4490 (2)0.41422 (11)0.0179 (4)
H30.6159660.4800710.4404040.021*
C40.9441 (3)0.2544 (2)0.53183 (11)0.0172 (4)
C50.8831 (4)0.2159 (2)0.58929 (12)0.0215 (5)
H50.7569390.2432060.6085010.026*
C61.0022 (4)0.1390 (2)0.61890 (12)0.0216 (5)
H60.9589560.1135910.6581520.026*
C71.1868 (4)0.0991 (2)0.59038 (11)0.0190 (5)
C81.2509 (4)0.1360 (2)0.53339 (12)0.0212 (5)
H81.3775030.1088100.5144510.025*
C91.1293 (4)0.2130 (2)0.50399 (11)0.0192 (5)
H91.1724520.2378530.4645850.023*
C100.7455 (3)0.4897 (2)0.35101 (11)0.0170 (4)
C110.5933 (4)0.5627 (2)0.33085 (11)0.0184 (4)
H110.4813480.5869840.3581830.022*
C120.6081 (4)0.5989 (2)0.27056 (11)0.0209 (5)
C130.7660 (4)0.5665 (2)0.22861 (12)0.0247 (5)
H130.7706570.5919760.1870560.030*
C140.9179 (4)0.4950 (3)0.24956 (12)0.0276 (5)
H141.0301150.4718040.2221030.033*
C150.9086 (4)0.4569 (2)0.30975 (12)0.0229 (5)
H151.0141600.4079120.3231170.027*
I21.34320 (2)1.22178 (2)0.27403 (2)0.02419 (5)
F20.2840 (2)0.90338 (13)0.06543 (8)0.0326 (3)
O20.6838 (2)0.64905 (15)0.07814 (8)0.0209 (3)
C160.6377 (3)0.7580 (2)0.08590 (11)0.0163 (4)
C170.4295 (3)0.7795 (2)0.05074 (11)0.0179 (4)
H170.3895370.8630060.0599150.021*
C180.2975 (3)0.6819 (2)0.00618 (11)0.0159 (4)
H180.3466460.6008440.0013020.019*
C190.7950 (3)0.8707 (2)0.13102 (11)0.0160 (4)
C200.9986 (3)0.8468 (2)0.15839 (12)0.0192 (5)
H201.0309030.7615120.1482110.023*
C211.1530 (4)0.9455 (2)0.19995 (12)0.0201 (5)
H211.2904450.9285460.2185370.024*
C221.1047 (3)1.0695 (2)0.21416 (11)0.0184 (4)
C230.9043 (4)1.0961 (2)0.18863 (12)0.0218 (5)
H230.8720021.1813880.1995810.026*
C240.7505 (4)0.9956 (2)0.14655 (12)0.0210 (5)
H240.6130471.0130140.1282150.025*
C250.0865 (3)0.6851 (2)0.03245 (11)0.0151 (4)
C260.0024 (4)0.7995 (2)0.03130 (11)0.0192 (5)
H260.0849470.8803090.0063660.023*
C270.2018 (4)0.7921 (2)0.06701 (12)0.0211 (5)
C280.3296 (4)0.6781 (2)0.10412 (12)0.0212 (5)
H280.4707380.6772400.1279920.025*
C290.2463 (4)0.5647 (2)0.10560 (11)0.0196 (5)
H290.3309170.4845260.1306580.024*
C300.0388 (4)0.5682 (2)0.07041 (11)0.0176 (4)
H300.0182870.4903060.0722120.021*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.02484 (8)0.02027 (8)0.02522 (9)0.00525 (6)0.00598 (6)0.00778 (6)
F10.0384 (8)0.0314 (8)0.0261 (8)0.0128 (7)0.0025 (6)0.0131 (6)
O10.0326 (10)0.0420 (11)0.0330 (10)0.0238 (9)0.0176 (8)0.0219 (9)
C10.0180 (11)0.0194 (11)0.0202 (11)0.0026 (9)0.0011 (9)0.0067 (9)
C20.0187 (11)0.0178 (11)0.0183 (11)0.0038 (9)0.0047 (9)0.0053 (9)
C30.0167 (10)0.0176 (11)0.0194 (11)0.0031 (8)0.0030 (8)0.0042 (9)
C40.0166 (10)0.0161 (10)0.0186 (11)0.0026 (8)0.0002 (8)0.0046 (9)
C50.0192 (11)0.0257 (12)0.0231 (12)0.0065 (9)0.0045 (9)0.0102 (10)
C60.0239 (12)0.0232 (12)0.0194 (11)0.0015 (9)0.0029 (9)0.0099 (10)
C70.0208 (11)0.0152 (10)0.0196 (11)0.0027 (9)0.0049 (9)0.0043 (9)
C80.0183 (11)0.0243 (12)0.0201 (11)0.0051 (9)0.0023 (9)0.0028 (9)
C90.0220 (11)0.0220 (12)0.0149 (11)0.0047 (9)0.0041 (9)0.0060 (9)
C100.0188 (11)0.0149 (10)0.0155 (11)0.0002 (8)0.0008 (8)0.0027 (8)
C110.0206 (11)0.0161 (11)0.0181 (11)0.0029 (9)0.0022 (9)0.0038 (9)
C120.0253 (12)0.0160 (11)0.0190 (11)0.0004 (9)0.0054 (9)0.0047 (9)
C130.0317 (13)0.0265 (13)0.0150 (11)0.0015 (10)0.0016 (9)0.0076 (10)
C140.0271 (13)0.0366 (14)0.0203 (12)0.0065 (11)0.0082 (10)0.0067 (11)
C150.0221 (12)0.0272 (13)0.0219 (12)0.0088 (10)0.0043 (9)0.0079 (10)
I20.02082 (8)0.01741 (8)0.02992 (9)0.00249 (6)0.00759 (6)0.00138 (6)
F20.0301 (8)0.0217 (7)0.0454 (9)0.0113 (6)0.0086 (7)0.0080 (7)
O20.0214 (8)0.0169 (8)0.0238 (8)0.0044 (6)0.0008 (6)0.0044 (7)
C160.0157 (10)0.0176 (11)0.0161 (11)0.0031 (8)0.0034 (8)0.0045 (9)
C170.0167 (10)0.0172 (11)0.0205 (11)0.0041 (8)0.0012 (8)0.0056 (9)
C180.0154 (10)0.0175 (11)0.0162 (10)0.0030 (8)0.0036 (8)0.0060 (9)
C190.0147 (10)0.0183 (11)0.0153 (10)0.0032 (8)0.0018 (8)0.0047 (9)
C200.0190 (11)0.0166 (11)0.0215 (11)0.0054 (9)0.0007 (9)0.0030 (9)
C210.0154 (10)0.0225 (12)0.0235 (12)0.0064 (9)0.0003 (9)0.0069 (10)
C220.0168 (10)0.0184 (11)0.0179 (11)0.0005 (8)0.0010 (8)0.0027 (9)
C230.0206 (11)0.0163 (11)0.0266 (12)0.0052 (9)0.0019 (9)0.0019 (9)
C240.0174 (11)0.0202 (11)0.0246 (12)0.0046 (9)0.0031 (9)0.0049 (10)
C250.0150 (10)0.0176 (11)0.0134 (10)0.0023 (8)0.0031 (8)0.0049 (8)
C260.0209 (11)0.0156 (11)0.0203 (11)0.0019 (9)0.0007 (9)0.0043 (9)
C270.0244 (12)0.0203 (11)0.0222 (12)0.0090 (9)0.0020 (9)0.0095 (9)
C280.0162 (10)0.0294 (13)0.0185 (11)0.0032 (9)0.0000 (9)0.0079 (10)
C290.0199 (11)0.0201 (11)0.0160 (11)0.0013 (9)0.0012 (9)0.0019 (9)
C300.0215 (11)0.0171 (11)0.0145 (10)0.0040 (9)0.0032 (8)0.0039 (9)
Geometric parameters (Å, º) top
I1—C72.092 (2)I2—C222.100 (2)
F1—C121.363 (3)F2—C271.363 (2)
O1—C11.222 (3)O2—C161.228 (3)
C1—C21.479 (3)C16—C171.479 (3)
C1—C41.495 (3)C16—C191.501 (3)
C2—H20.9500C17—H170.9500
C2—C31.337 (3)C17—C181.334 (3)
C3—H30.9500C18—H180.9500
C3—C101.462 (3)C18—C251.460 (3)
C4—C51.393 (3)C19—C201.401 (3)
C4—C91.397 (3)C19—C241.386 (3)
C5—H50.9500C20—H200.9500
C5—C61.381 (3)C20—C211.381 (3)
C6—H60.9500C21—H210.9500
C6—C71.394 (3)C21—C221.384 (3)
C7—C81.382 (3)C22—C231.383 (3)
C8—H80.9500C23—H230.9500
C8—C91.388 (3)C23—C241.393 (3)
C9—H90.9500C24—H240.9500
C10—C111.394 (3)C25—C261.400 (3)
C10—C151.395 (3)C25—C301.399 (3)
C11—H110.9500C26—H260.9500
C11—C121.378 (3)C26—C271.371 (3)
C12—C131.377 (3)C27—C281.377 (3)
C13—H130.9500C28—H280.9500
C13—C141.387 (3)C28—C291.388 (3)
C14—H140.9500C29—H290.9500
C14—C151.383 (3)C29—C301.393 (3)
C15—H150.9500C30—H300.9500
O1—C1—C2120.6 (2)O2—C16—C17120.59 (19)
O1—C1—C4118.9 (2)O2—C16—C19119.74 (19)
C2—C1—C4120.5 (2)C17—C16—C19119.66 (18)
C1—C2—H2119.8C16—C17—H17119.9
C3—C2—C1120.4 (2)C18—C17—C16120.2 (2)
C3—C2—H2119.8C18—C17—H17119.9
C2—C3—H3116.6C17—C18—H18116.2
C2—C3—C10126.8 (2)C17—C18—C25127.6 (2)
C10—C3—H3116.6C25—C18—H18116.2
C5—C4—C1117.7 (2)C20—C19—C16117.37 (19)
C5—C4—C9118.7 (2)C24—C19—C16123.86 (19)
C9—C4—C1123.6 (2)C24—C19—C20118.8 (2)
C4—C5—H5119.4C19—C20—H20119.6
C6—C5—C4121.3 (2)C21—C20—C19120.9 (2)
C6—C5—H5119.4C21—C20—H20119.6
C5—C6—H6120.5C20—C21—H21120.5
C5—C6—C7119.1 (2)C20—C21—C22119.1 (2)
C7—C6—H6120.5C22—C21—H21120.5
C6—C7—I1118.55 (17)C21—C22—I2119.47 (15)
C8—C7—I1120.68 (17)C23—C22—I2119.01 (17)
C8—C7—C6120.8 (2)C23—C22—C21121.5 (2)
C7—C8—H8120.2C22—C23—H23120.6
C7—C8—C9119.6 (2)C22—C23—C24118.8 (2)
C9—C8—H8120.2C24—C23—H23120.6
C4—C9—H9119.7C19—C24—C23121.0 (2)
C8—C9—C4120.6 (2)C19—C24—H24119.5
C8—C9—H9119.7C23—C24—H24119.5
C11—C10—C3118.7 (2)C26—C25—C18122.73 (19)
C11—C10—C15118.9 (2)C30—C25—C18118.18 (19)
C15—C10—C3122.4 (2)C30—C25—C26119.07 (19)
C10—C11—H11120.6C25—C26—H26120.8
C12—C11—C10118.8 (2)C27—C26—C25118.4 (2)
C12—C11—H11120.6C27—C26—H26120.8
F1—C12—C11118.5 (2)F2—C27—C26118.4 (2)
F1—C12—C13118.1 (2)F2—C27—C28118.0 (2)
C13—C12—C11123.4 (2)C26—C27—C28123.7 (2)
C12—C13—H13121.4C27—C28—H28121.0
C12—C13—C14117.2 (2)C27—C28—C29118.0 (2)
C14—C13—H13121.4C29—C28—H28121.0
C13—C14—H14119.5C28—C29—H29120.0
C15—C14—C13121.1 (2)C28—C29—C30120.1 (2)
C15—C14—H14119.5C30—C29—H29120.0
C10—C15—H15119.7C25—C30—H30119.6
C14—C15—C10120.6 (2)C29—C30—C25120.7 (2)
C14—C15—H15119.7C29—C30—H30119.6
I1—C7—C8—C9179.84 (16)I2—C22—C23—C24177.27 (17)
F1—C12—C13—C14178.8 (2)F2—C27—C28—C29179.8 (2)
O1—C1—C2—C30.2 (3)O2—C16—C17—C185.1 (3)
O1—C1—C4—C57.0 (3)O2—C16—C19—C205.0 (3)
O1—C1—C4—C9171.8 (2)O2—C16—C19—C24175.4 (2)
C1—C2—C3—C10179.8 (2)C16—C17—C18—C25179.4 (2)
C1—C4—C5—C6178.6 (2)C16—C19—C20—C21179.5 (2)
C1—C4—C9—C8178.3 (2)C16—C19—C24—C23179.7 (2)
C2—C1—C4—C5173.0 (2)C17—C16—C19—C20174.6 (2)
C2—C1—C4—C98.2 (3)C17—C16—C19—C245.1 (3)
C2—C3—C10—C11175.5 (2)C17—C18—C25—C265.7 (4)
C2—C3—C10—C153.6 (4)C17—C18—C25—C30172.4 (2)
C3—C10—C11—C12178.6 (2)C18—C25—C26—C27177.3 (2)
C3—C10—C15—C14178.5 (2)C18—C25—C30—C29176.9 (2)
C4—C1—C2—C3179.7 (2)C19—C16—C17—C18174.4 (2)
C4—C5—C6—C70.1 (3)C19—C20—C21—C220.3 (3)
C5—C4—C9—C80.5 (3)C20—C19—C24—C230.1 (3)
C5—C6—C7—I1179.95 (17)C20—C21—C22—I2177.51 (17)
C5—C6—C7—C80.2 (3)C20—C21—C22—C231.1 (4)
C6—C7—C8—C90.4 (3)C21—C22—C23—C241.4 (4)
C7—C8—C9—C40.5 (3)C22—C23—C24—C190.8 (4)
C9—C4—C5—C60.3 (3)C24—C19—C20—C210.2 (3)
C10—C11—C12—F1179.47 (19)C25—C26—C27—F2179.53 (19)
C10—C11—C12—C130.2 (3)C25—C26—C27—C280.0 (4)
C11—C10—C15—C140.6 (3)C26—C25—C30—C291.2 (3)
C11—C12—C13—C140.8 (3)C26—C27—C28—C290.3 (4)
C12—C13—C14—C150.7 (4)C27—C28—C29—C300.2 (3)
C13—C14—C15—C100.1 (4)C28—C29—C30—C251.0 (3)
C15—C10—C11—C120.5 (3)C30—C25—C26—C270.8 (3)
(2E)-1-(4-Iodophenyl)-3-(4-nitrophenyl)prop-2-en-1-one (ep8p) top
Crystal data top
C15H10INO3F(000) = 1472
Mr = 379.14Dx = 1.882 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 17.9016 (7) ÅCell parameters from 8739 reflections
b = 5.8824 (2) Åθ = 2.3–29.6°
c = 25.4871 (9) ŵ = 2.40 mm1
β = 94.427 (2)°T = 100 K
V = 2675.89 (17) Å3Plate, clear yellow
Z = 80.47 × 0.19 × 0.08 mm
Data collection top
Bruker APEXII Kappa CCD area detector
diffractometer
6154 independent reflections
Radiation source: fine-focus sealed tube4831 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.051
φ and ω scansθmax = 27.5°, θmin = 1.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
h = 2323
Tmin = 0.581, Tmax = 0.746k = 77
36371 measured reflectionsl = 3333
Refinement top
Refinement on F2Primary atom site location: iterative
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072H-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 parametersΔρmax = 0.92 e Å3
0 restraintsΔρmin = 0.80 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.46827 (2)0.18749 (4)0.89263 (2)0.02620 (7)
O10.68944 (14)0.6988 (4)0.70781 (9)0.0251 (5)
N10.87643 (15)0.1862 (5)0.48753 (11)0.0190 (6)
C10.67394 (18)0.4972 (5)0.71254 (13)0.0188 (7)
O20.92791 (17)0.1047 (5)0.46719 (13)0.0473 (8)
C20.70117 (18)0.3212 (6)0.67699 (13)0.0214 (7)
H20.6832580.1695600.6786920.026*
O30.84712 (15)0.3676 (4)0.47756 (10)0.0300 (6)
C30.75063 (18)0.3755 (5)0.64273 (13)0.0182 (7)
H30.7681370.5280130.6435820.022*
C40.62526 (18)0.4217 (5)0.75461 (13)0.0192 (7)
C50.57507 (19)0.5762 (5)0.77384 (13)0.0204 (7)
H50.5716660.7255560.7596550.024*
C60.53000 (19)0.5148 (6)0.81344 (14)0.0227 (7)
H60.4951380.6199720.8258370.027*
C70.53647 (18)0.2985 (6)0.83465 (13)0.0200 (7)
C80.58707 (19)0.1446 (6)0.81632 (14)0.0218 (7)
H80.5917960.0025570.8315620.026*
C90.63056 (18)0.2040 (5)0.77610 (13)0.0208 (7)
H90.6641320.0965090.7630570.025*
C100.78105 (17)0.2247 (5)0.60376 (12)0.0175 (7)
C110.84278 (18)0.2979 (5)0.57823 (13)0.0189 (7)
H110.8634880.4433700.5865490.023*
C120.87495 (18)0.1652 (6)0.54110 (13)0.0213 (7)
H120.9176500.2161210.5245190.026*
C130.84279 (18)0.0432 (5)0.52907 (13)0.0181 (6)
C140.78134 (19)0.1245 (5)0.55299 (13)0.0193 (7)
H140.7605770.2691510.5438570.023*
C150.75071 (18)0.0098 (5)0.59061 (13)0.0197 (7)
H150.7088000.0440260.6076710.024*
I21.03760 (2)0.56634 (4)0.61108 (2)0.02643 (7)
N20.61577 (15)0.1927 (5)1.01386 (11)0.0214 (6)
O40.80218 (13)1.0460 (4)0.78924 (9)0.0234 (5)
O50.56272 (16)0.2723 (5)1.03340 (12)0.0398 (7)
O60.64466 (14)0.0096 (4)1.02509 (10)0.0278 (6)
C160.81836 (17)0.8438 (5)0.78593 (13)0.0181 (7)
C170.79033 (18)0.6748 (6)0.82274 (13)0.0204 (7)
H170.8043120.5196740.8200700.024*
C180.74621 (18)0.7376 (5)0.85914 (13)0.0191 (7)
H180.7339380.8945800.8601840.023*
C190.86846 (17)0.7688 (5)0.74496 (13)0.0167 (6)
C200.88392 (18)0.9224 (5)0.70561 (13)0.0201 (7)
H200.8608911.0679660.7049960.024*
C210.93160 (18)0.8689 (5)0.66763 (13)0.0201 (7)
H210.9410170.9753050.6408790.024*
C220.96584 (18)0.6563 (6)0.66908 (13)0.0198 (7)
C230.95161 (18)0.4993 (5)0.70757 (13)0.0203 (7)
H230.9751370.3544600.7080910.024*
C240.90279 (18)0.5546 (5)0.74538 (13)0.0200 (7)
H240.8926250.4467850.7716520.024*
C250.71394 (18)0.5920 (5)0.89822 (13)0.0189 (7)
C260.65261 (18)0.6727 (6)0.92375 (13)0.0198 (7)
H260.6332720.8197740.9153790.024*
C270.61967 (18)0.5430 (5)0.96082 (13)0.0198 (7)
H270.5772320.5967840.9772790.024*
C280.65047 (17)0.3322 (5)0.97321 (13)0.0179 (6)
C290.71203 (18)0.2460 (5)0.94951 (13)0.0189 (7)
H290.7322230.1011360.9590700.023*
C300.74283 (18)0.3765 (5)0.91181 (13)0.0198 (7)
H300.7843070.3195330.8947460.024*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.02316 (12)0.03385 (13)0.02215 (12)0.00656 (10)0.00543 (9)0.00175 (10)
O10.0314 (13)0.0209 (12)0.0238 (13)0.0031 (10)0.0064 (11)0.0010 (10)
N10.0187 (13)0.0190 (14)0.0192 (14)0.0050 (12)0.0007 (11)0.0050 (11)
C10.0196 (16)0.0191 (16)0.0178 (16)0.0026 (13)0.0013 (13)0.0005 (13)
O20.0505 (18)0.0415 (17)0.054 (2)0.0123 (14)0.0310 (16)0.0199 (15)
C20.0240 (17)0.0175 (16)0.0225 (17)0.0001 (14)0.0007 (14)0.0000 (14)
O30.0374 (15)0.0239 (13)0.0297 (14)0.0004 (11)0.0094 (12)0.0033 (11)
C30.0208 (16)0.0158 (15)0.0179 (16)0.0005 (12)0.0013 (13)0.0002 (12)
C40.0204 (16)0.0193 (16)0.0173 (16)0.0008 (13)0.0016 (13)0.0018 (13)
C50.0260 (17)0.0141 (15)0.0208 (17)0.0026 (13)0.0003 (14)0.0018 (13)
C60.0203 (17)0.0218 (17)0.0257 (18)0.0033 (13)0.0003 (14)0.0030 (14)
C70.0201 (16)0.0217 (16)0.0184 (16)0.0044 (14)0.0021 (13)0.0005 (13)
C80.0235 (17)0.0189 (16)0.0225 (17)0.0007 (13)0.0008 (14)0.0036 (13)
C90.0195 (16)0.0168 (16)0.0263 (18)0.0060 (13)0.0035 (14)0.0037 (14)
C100.0178 (16)0.0193 (15)0.0154 (16)0.0016 (13)0.0016 (13)0.0041 (13)
C110.0215 (16)0.0152 (15)0.0199 (16)0.0009 (13)0.0012 (13)0.0020 (13)
C120.0188 (16)0.0228 (17)0.0228 (17)0.0014 (14)0.0053 (14)0.0025 (14)
C130.0196 (16)0.0172 (15)0.0173 (16)0.0057 (13)0.0007 (13)0.0015 (13)
C140.0238 (17)0.0149 (15)0.0189 (17)0.0015 (13)0.0005 (14)0.0024 (12)
C150.0199 (16)0.0179 (16)0.0212 (17)0.0000 (13)0.0017 (14)0.0015 (13)
I20.02098 (12)0.03531 (14)0.02379 (12)0.00022 (10)0.00677 (9)0.00353 (10)
N20.0216 (14)0.0216 (14)0.0204 (15)0.0047 (12)0.0014 (12)0.0072 (12)
O40.0257 (13)0.0186 (12)0.0264 (13)0.0016 (10)0.0059 (10)0.0014 (10)
O50.0422 (16)0.0365 (15)0.0446 (17)0.0118 (13)0.0279 (14)0.0095 (13)
O60.0344 (14)0.0192 (12)0.0309 (14)0.0012 (11)0.0100 (12)0.0044 (10)
C160.0168 (15)0.0177 (16)0.0194 (16)0.0014 (13)0.0019 (13)0.0021 (13)
C170.0202 (16)0.0186 (16)0.0225 (17)0.0013 (14)0.0024 (14)0.0007 (13)
C180.0200 (16)0.0171 (16)0.0200 (17)0.0012 (13)0.0005 (13)0.0017 (13)
C190.0159 (15)0.0155 (15)0.0188 (16)0.0028 (12)0.0011 (13)0.0002 (12)
C200.0225 (17)0.0154 (15)0.0216 (17)0.0040 (13)0.0026 (14)0.0017 (13)
C210.0217 (17)0.0190 (16)0.0196 (17)0.0005 (13)0.0005 (14)0.0037 (13)
C220.0179 (16)0.0218 (16)0.0199 (17)0.0032 (13)0.0028 (13)0.0036 (13)
C230.0199 (16)0.0142 (15)0.0267 (18)0.0027 (12)0.0015 (14)0.0031 (13)
C240.0182 (16)0.0181 (16)0.0240 (17)0.0000 (13)0.0041 (13)0.0043 (13)
C250.0199 (16)0.0186 (16)0.0180 (16)0.0026 (13)0.0011 (13)0.0033 (13)
C260.0242 (17)0.0173 (15)0.0181 (16)0.0031 (14)0.0023 (13)0.0021 (13)
C270.0210 (16)0.0195 (16)0.0193 (16)0.0019 (13)0.0037 (13)0.0041 (13)
C280.0177 (15)0.0207 (16)0.0156 (15)0.0006 (13)0.0030 (13)0.0028 (13)
C290.0193 (16)0.0165 (15)0.0209 (17)0.0024 (13)0.0015 (13)0.0014 (13)
C300.0187 (16)0.0197 (16)0.0212 (17)0.0021 (13)0.0039 (14)0.0026 (13)
Geometric parameters (Å, º) top
I1—C72.093 (3)I2—C222.100 (3)
O1—C11.226 (4)N2—O51.201 (4)
N1—O21.192 (4)N2—O61.219 (3)
N1—O31.207 (3)N2—C281.494 (4)
N1—C131.513 (4)O4—C161.229 (4)
C1—C21.483 (5)C16—C171.481 (4)
C1—C41.500 (5)C16—C191.495 (5)
C2—H20.9500C17—H170.9500
C2—C31.330 (5)C17—C181.317 (5)
C3—H30.9500C18—H180.9500
C3—C101.467 (4)C18—C251.466 (5)
C4—C51.394 (4)C19—C201.393 (4)
C4—C91.393 (4)C19—C241.402 (4)
C5—H50.9500C20—H200.9500
C5—C61.388 (5)C20—C211.376 (5)
C6—H60.9500C21—H210.9500
C6—C71.384 (5)C21—C221.392 (4)
C7—C81.387 (5)C22—C231.385 (5)
C8—H80.9500C23—H230.9500
C8—C91.379 (5)C23—C241.389 (5)
C9—H90.9500C24—H240.9500
C10—C111.393 (4)C25—C261.402 (4)
C10—C151.406 (4)C25—C301.403 (4)
C11—H110.9500C26—H260.9500
C11—C121.386 (5)C26—C271.382 (5)
C12—H120.9500C27—H270.9500
C12—C131.379 (5)C27—C281.383 (4)
C13—C141.384 (5)C28—C291.393 (4)
C14—H140.9500C29—H290.9500
C14—C151.388 (5)C29—C301.378 (5)
C15—H150.9500C30—H300.9500
O2—N1—O3127.0 (3)O5—N2—O6125.6 (3)
O2—N1—C13116.3 (3)O5—N2—C28117.3 (3)
O3—N1—C13116.7 (3)O6—N2—C28117.2 (3)
O1—C1—C2121.8 (3)O4—C16—C17120.9 (3)
O1—C1—C4120.3 (3)O4—C16—C19119.4 (3)
C2—C1—C4117.8 (3)C17—C16—C19119.7 (3)
C1—C2—H2120.0C16—C17—H17119.7
C3—C2—C1120.0 (3)C18—C17—C16120.6 (3)
C3—C2—H2120.0C18—C17—H17119.7
C2—C3—H3116.6C17—C18—H18116.4
C2—C3—C10126.9 (3)C17—C18—C25127.2 (3)
C10—C3—H3116.6C25—C18—H18116.4
C5—C4—C1118.9 (3)C20—C19—C16118.3 (3)
C9—C4—C1121.8 (3)C20—C19—C24118.5 (3)
C9—C4—C5119.2 (3)C24—C19—C16123.1 (3)
C4—C5—H5119.6C19—C20—H20119.1
C6—C5—C4120.8 (3)C21—C20—C19121.8 (3)
C6—C5—H5119.6C21—C20—H20119.1
C5—C6—H6120.4C20—C21—H21120.6
C7—C6—C5119.2 (3)C20—C21—C22118.8 (3)
C7—C6—H6120.4C22—C21—H21120.6
C6—C7—I1121.8 (2)C21—C22—I2120.0 (2)
C6—C7—C8120.4 (3)C23—C22—I2119.1 (2)
C8—C7—I1117.8 (2)C23—C22—C21120.9 (3)
C7—C8—H8119.8C22—C23—H23120.2
C9—C8—C7120.4 (3)C22—C23—C24119.7 (3)
C9—C8—H8119.8C24—C23—H23120.2
C4—C9—H9120.0C19—C24—H24119.9
C8—C9—C4120.0 (3)C23—C24—C19120.3 (3)
C8—C9—H9120.0C23—C24—H24119.9
C11—C10—C3118.6 (3)C26—C25—C18118.8 (3)
C11—C10—C15118.2 (3)C26—C25—C30118.6 (3)
C15—C10—C3123.2 (3)C30—C25—C18122.6 (3)
C10—C11—H11118.9C25—C26—H26119.3
C12—C11—C10122.1 (3)C27—C26—C25121.4 (3)
C12—C11—H11118.9C27—C26—H26119.3
C11—C12—H12121.2C26—C27—H27121.1
C13—C12—C11117.7 (3)C26—C27—C28117.9 (3)
C13—C12—H12121.2C28—C27—H27121.1
C12—C13—N1117.9 (3)C27—C28—N2118.1 (3)
C12—C13—C14122.8 (3)C27—C28—C29122.8 (3)
C14—C13—N1119.3 (3)C29—C28—N2119.1 (3)
C13—C14—H14120.7C28—C29—H29120.9
C13—C14—C15118.5 (3)C30—C29—C28118.2 (3)
C15—C14—H14120.7C30—C29—H29120.9
C10—C15—H15119.6C25—C30—H30119.5
C14—C15—C10120.7 (3)C29—C30—C25121.1 (3)
C14—C15—H15119.6C29—C30—H30119.5
I1—C7—C8—C9176.4 (3)I2—C22—C23—C24178.4 (2)
O1—C1—C2—C37.9 (5)N2—C28—C29—C30179.5 (3)
O1—C1—C4—C525.1 (5)O4—C16—C17—C181.4 (5)
O1—C1—C4—C9152.8 (3)O4—C16—C19—C2011.8 (5)
N1—C13—C14—C15179.3 (3)O4—C16—C19—C24165.7 (3)
C1—C2—C3—C10177.7 (3)O5—N2—C28—C270.2 (4)
C1—C4—C5—C6178.8 (3)O5—N2—C28—C29179.9 (3)
C1—C4—C9—C8177.2 (3)O6—N2—C28—C27178.5 (3)
O2—N1—C13—C121.6 (4)O6—N2—C28—C291.5 (4)
O2—N1—C13—C14177.9 (3)C16—C17—C18—C25179.9 (3)
C2—C1—C4—C5154.0 (3)C16—C19—C20—C21177.6 (3)
C2—C1—C4—C928.0 (5)C16—C19—C24—C23176.9 (3)
C2—C3—C10—C11167.7 (3)C17—C16—C19—C20169.6 (3)
C2—C3—C10—C1512.6 (5)C17—C16—C19—C2412.9 (5)
O3—N1—C13—C12179.7 (3)C17—C18—C25—C26162.2 (3)
O3—N1—C13—C140.2 (4)C17—C18—C25—C3018.9 (5)
C3—C10—C11—C12179.7 (3)C18—C25—C26—C27179.8 (3)
C3—C10—C15—C14179.3 (3)C18—C25—C30—C29178.7 (3)
C4—C1—C2—C3173.0 (3)C19—C16—C17—C18179.9 (3)
C4—C5—C6—C71.4 (5)C19—C20—C21—C220.7 (5)
C5—C4—C9—C80.7 (5)C20—C19—C24—C230.6 (5)
C5—C6—C7—I1177.9 (2)C20—C21—C22—I2179.0 (2)
C5—C6—C7—C80.4 (5)C20—C21—C22—C230.8 (5)
C6—C7—C8—C91.2 (5)C21—C22—C23—C240.2 (5)
C7—C8—C9—C41.7 (5)C22—C23—C24—C190.5 (5)
C9—C4—C5—C60.8 (5)C24—C19—C20—C210.0 (5)
C10—C11—C12—C131.3 (5)C25—C26—C27—C281.8 (5)
C11—C10—C15—C140.4 (5)C26—C25—C30—C290.2 (5)
C11—C12—C13—N1178.4 (3)C26—C27—C28—N2179.1 (3)
C11—C12—C13—C141.0 (5)C26—C27—C28—C290.8 (5)
C12—C13—C14—C150.1 (5)C27—C28—C29—C300.6 (5)
C13—C14—C15—C100.6 (5)C28—C29—C30—C251.1 (5)
C15—C10—C11—C120.6 (5)C30—C25—C26—C271.3 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9···O4i0.952.533.202 (4)128
C14—H14···O6ii0.952.533.370 (4)148
C29—H29···O3iii0.952.493.324 (4)147
Symmetry codes: (i) x, y1, z; (ii) x, y1/2, z1/2; (iii) x, y1/2, z+1/2.
 

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