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The potential of pyrimidines to serve as ditopic halogen-bond acceptors is explored. The halogen-bonded cocrystals formed from solutions of either 5,5′-bi­pyrimidine (C8H6N4) or 1,2-bis­(pyrimidin-5-yl)ethyne (C10H6N4) and 2 molar equivalents of 1,3-di­iodo­tetra­fluoro­benzene (C6F4I2) have a 1:1 com­position. Each pyrimidine moiety acts as a single halogen-bond acceptor and the bi­pyrimidines act as ditopic halogen-bond acceptors. In contrast, the activated pyrimidines 2- and 5-{[4-(di­methyl­amino)­phen­yl]ethyn­yl}pyrimidine (C14H13N3) are ditopic halogen-bond acceptors, and 1:1 halogen-bonded cocrystals are formed from 1:1 mixtures of each of the activated pyrimidines and either 1,2- or 1,3-di­iodo­tetra­fluoro­benzene. A 1:1 cocrystal was also formed between 2-{[4-(di­methyl­amino)­phen­yl]ethyn­yl}pyrimidine and 1,4-di­iodo­tetra­fluoro­benzene, while a 2:1 cocrystal was formed between 5-{[4-(di­methyl­amino)­phen­yl]ethyn­yl}pyrimidine and 1,4-di­iodo­tetra­fluoro­benzene.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229620005082/fn3332sup1.cif
Contains datablocks 1_eb897_a, 2_eb843_a, 3_eb797_a, 4_eb814_a, 5_eb948_a, 6_eb951_a_F, 7_eb945_a_tw, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620005082/fn33321_eb897_asup2.hkl
Contains datablock 1_eb897_a

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620005082/fn33322_eb843_asup3.hkl
Contains datablock 2_eb843_a

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620005082/fn33323_eb797_asup4.hkl
Contains datablock 3_eb797_a

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620005082/fn33324_eb814_asup5.hkl
Contains datablock 4_eb814_a

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620005082/fn33325_eb948_asup6.hkl
Contains datablock 5_eb948_a

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620005082/fn33326_eb951_a_Fsup7.hkl
Contains datablock 6_eb951_a_F

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620005082/fn33327_eb945_a_twsup8.hkl
Contains datablock 7_eb945_a_tw

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229620005082/fn33321_eb897_asup9.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229620005082/fn33322_eb843_asup10.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229620005082/fn33323_eb797_asup11.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229620005082/fn33324_eb814_asup12.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229620005082/fn33325_eb948_asup13.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229620005082/fn33326_eb951_a_Fsup14.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229620005082/fn33327_eb945_a_twsup15.cml
Supplementary material

CCDC references: 1996176; 1996175; 1996174; 1996173; 1996172; 1996171; 1996170

Computing details top

For all structures, data collection: SMART (Bruker, 2016); cell refinement: SMART (Bruker, 2016); data reduction: SAINT (Bruker, 2016). Program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a) for 1_eb897_a, 2_eb843_a; SHELXT2018 (Sheldrick, 2015) for 3_eb797_a, 4_eb814_a, 5_eb948_a, 6_eb951_a_F, 7_eb945_a_tw. Program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b) for 1_eb897_a, 2_eb843_a; SHELXL2018 (Sheldrick, 2015) for 3_eb797_a, 4_eb814_a, 5_eb948_a, 6_eb951_a_F, 7_eb945_a_tw. For all structures, molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: X-SEED (Barbour, 2001).

1,2-Bis(pyrimidin-5-yl)ethyne–1,2,3,5-tetrafluoro-4,6-diiodobenzene (1/1) (1_eb897_a) top
Crystal data top
C10H6N4·C6F4I2F(000) = 2176
Mr = 584.05Dx = 2.282 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 27.2812 (12) ÅCell parameters from 9912 reflections
b = 6.2100 (3) Åθ = 2.9–27.2°
c = 20.9742 (9) ŵ = 3.75 mm1
β = 106.931 (1)°T = 100 K
V = 3399.4 (3) Å3Cut, colourless
Z = 80.2 × 0.1 × 0.03 mm
Data collection top
Bruker APEXII CCD
diffractometer
3766 independent reflections
Radiation source: fine-focus sealed tube3544 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
Detector resolution: 8.3660 pixels mm-1θmax = 27.2°, θmin = 2.0°
phi and ω scansh = 3434
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
k = 77
Tmin = 0.644, Tmax = 0.894l = 2626
19984 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.020H-atom parameters constrained
wR(F2) = 0.050 w = 1/[σ2(Fo2) + (0.0273P)2 + 4.1245P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.004
3766 reflectionsΔρmax = 1.22 e Å3
235 parametersΔρmin = 0.46 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
I10.71386 (2)0.64479 (2)0.38942 (2)0.01647 (5)
F10.77768 (5)0.7557 (2)0.28731 (7)0.0187 (3)
N10.64733 (8)0.8906 (3)0.44851 (10)0.0166 (4)
C10.61871 (9)0.7914 (4)0.48177 (12)0.0176 (5)
H10.6185340.6385590.4832440.021*
I20.87690 (2)0.61878 (2)0.24466 (2)0.01686 (5)
F20.88729 (5)0.1537 (2)0.31325 (7)0.0221 (3)
N20.61952 (7)1.2324 (3)0.47719 (10)0.0187 (4)
C20.64661 (9)1.1054 (4)0.44840 (12)0.0173 (5)
H20.6674711.1754900.4255360.021*
F30.83918 (5)0.0311 (2)0.39399 (7)0.0224 (3)
N30.44514 (8)0.6426 (3)0.68510 (11)0.0188 (4)
C30.59090 (9)1.1307 (4)0.50990 (12)0.0173 (5)
H30.5709661.2146480.5309560.021*
F40.76310 (5)0.1776 (2)0.42656 (7)0.0208 (3)
N40.46927 (8)0.2967 (3)0.65483 (11)0.0213 (4)
C40.58901 (9)0.9068 (4)0.51447 (12)0.0151 (4)
C50.55827 (9)0.8022 (4)0.55049 (12)0.0194 (5)
C60.53333 (9)0.7184 (4)0.58159 (12)0.0189 (5)
C70.50276 (9)0.6167 (4)0.61884 (12)0.0168 (5)
C80.47516 (9)0.7373 (4)0.65275 (12)0.0193 (5)
H80.4776700.8899260.6529360.023*
C90.44393 (9)0.4276 (4)0.68436 (12)0.0198 (5)
H90.4227070.3609040.7073860.024*
C100.49836 (9)0.3937 (4)0.62182 (13)0.0193 (5)
H100.5168000.3066530.5994600.023*
C110.76858 (8)0.4738 (4)0.35771 (11)0.0149 (4)
C120.79342 (8)0.5618 (4)0.31458 (11)0.0146 (5)
C130.83388 (8)0.4621 (4)0.29861 (11)0.0150 (4)
C140.84753 (8)0.2595 (4)0.32529 (11)0.0159 (5)
C150.82325 (9)0.1620 (4)0.36694 (12)0.0161 (5)
C160.78434 (8)0.2708 (4)0.38301 (11)0.0156 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.01574 (8)0.01570 (9)0.02075 (9)0.00149 (5)0.00968 (6)0.00026 (6)
F10.0219 (7)0.0146 (7)0.0206 (7)0.0040 (5)0.0080 (6)0.0050 (5)
N10.0166 (10)0.0194 (10)0.0163 (10)0.0017 (8)0.0086 (8)0.0006 (8)
C10.0203 (12)0.0175 (11)0.0162 (12)0.0010 (9)0.0074 (9)0.0006 (9)
I20.01862 (9)0.01897 (9)0.01590 (9)0.00233 (5)0.00958 (6)0.00125 (5)
F20.0202 (7)0.0221 (7)0.0271 (8)0.0071 (6)0.0119 (6)0.0008 (6)
N20.0211 (10)0.0166 (10)0.0201 (10)0.0003 (8)0.0084 (8)0.0001 (8)
C20.0172 (11)0.0199 (12)0.0168 (12)0.0014 (9)0.0079 (9)0.0005 (9)
F30.0266 (7)0.0145 (7)0.0258 (8)0.0047 (6)0.0071 (6)0.0043 (6)
N30.0190 (10)0.0221 (11)0.0186 (11)0.0002 (8)0.0107 (8)0.0003 (8)
C30.0165 (11)0.0204 (12)0.0167 (12)0.0021 (9)0.0077 (9)0.0019 (9)
F40.0242 (7)0.0189 (7)0.0231 (8)0.0011 (6)0.0129 (6)0.0055 (6)
N40.0205 (10)0.0201 (10)0.0249 (11)0.0010 (8)0.0091 (9)0.0015 (9)
C40.0116 (10)0.0212 (11)0.0130 (11)0.0007 (9)0.0040 (9)0.0012 (9)
C50.0176 (11)0.0226 (12)0.0193 (12)0.0020 (9)0.0073 (10)0.0013 (10)
C60.0171 (11)0.0220 (12)0.0178 (12)0.0016 (9)0.0055 (9)0.0004 (10)
C70.0154 (11)0.0224 (12)0.0134 (11)0.0008 (9)0.0057 (9)0.0008 (9)
C80.0203 (12)0.0192 (12)0.0203 (12)0.0010 (9)0.0088 (10)0.0015 (10)
C90.0178 (11)0.0247 (12)0.0204 (12)0.0020 (10)0.0110 (10)0.0015 (10)
C100.0163 (11)0.0231 (12)0.0200 (13)0.0004 (9)0.0075 (10)0.0024 (10)
C110.0140 (10)0.0149 (11)0.0171 (11)0.0004 (8)0.0064 (9)0.0015 (9)
C120.0176 (11)0.0111 (11)0.0157 (12)0.0000 (8)0.0057 (9)0.0001 (8)
C130.0144 (10)0.0187 (11)0.0130 (11)0.0010 (9)0.0058 (9)0.0012 (9)
C140.0126 (10)0.0185 (11)0.0170 (11)0.0020 (9)0.0050 (9)0.0035 (9)
C150.0176 (11)0.0124 (10)0.0163 (12)0.0023 (8)0.0019 (9)0.0001 (8)
C160.0167 (11)0.0165 (11)0.0148 (11)0.0033 (9)0.0066 (9)0.0004 (9)
Geometric parameters (Å, º) top
I1—C112.092 (2)N4—C91.331 (3)
F1—C121.348 (3)N4—C101.339 (3)
N1—C21.334 (3)C4—C51.437 (3)
N1—C11.339 (3)C5—C61.191 (4)
C1—C41.401 (3)C6—C71.444 (3)
C1—H10.9500C7—C101.393 (3)
I2—C132.092 (2)C7—C81.395 (3)
F2—C141.353 (2)C8—H80.9500
N2—C31.339 (3)C9—H90.9500
N2—C21.339 (3)C10—H100.9500
C2—H20.9500C11—C161.387 (3)
F3—C151.343 (3)C11—C121.390 (3)
N3—C91.336 (3)C12—C131.389 (3)
N3—C81.342 (3)C13—C141.383 (3)
C3—C41.396 (3)C14—C151.381 (3)
C3—H30.9500C15—C161.380 (3)
F4—C161.347 (3)
C2—N1—C1116.7 (2)N4—C9—N3127.0 (2)
N1—C1—C4121.9 (2)N4—C9—H9116.5
N1—C1—H1119.1N3—C9—H9116.5
C4—C1—H1119.1N4—C10—C7122.8 (2)
C3—N2—C2115.7 (2)N4—C10—H10118.6
N1—C2—N2126.7 (2)C7—C10—H10118.6
N1—C2—H2116.6C16—C11—C12116.8 (2)
N2—C2—H2116.6C16—C11—I1120.67 (16)
C9—N3—C8116.7 (2)C12—C11—I1122.37 (17)
N2—C3—C4123.0 (2)F1—C12—C13118.23 (19)
N2—C3—H3118.5F1—C12—C11118.15 (19)
C4—C3—H3118.5C13—C12—C11123.6 (2)
C9—N4—C10115.6 (2)C14—C13—C12116.6 (2)
C3—C4—C1115.9 (2)C14—C13—I2120.95 (16)
C3—C4—C5121.7 (2)C12—C13—I2122.24 (17)
C1—C4—C5122.4 (2)F2—C14—C15117.6 (2)
C6—C5—C4178.5 (3)F2—C14—C13120.1 (2)
C5—C6—C7179.6 (3)C15—C14—C13122.2 (2)
C10—C7—C8116.4 (2)F3—C15—C16120.7 (2)
C10—C7—C6122.0 (2)F3—C15—C14120.2 (2)
C8—C7—C6121.6 (2)C16—C15—C14119.0 (2)
N3—C8—C7121.4 (2)F4—C16—C15117.9 (2)
N3—C8—H8119.3F4—C16—C11120.24 (19)
C7—C8—H8119.3C15—C16—C11121.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···N2i0.952.533.473 (3)175
C2—H2···F4ii0.952.603.370 (3)138
C8—H8···N4ii0.952.543.478 (3)171
Symmetry codes: (i) x, y1, z; (ii) x, y+1, z.
5,5'-Bipyrimidine–1,2,3,5-tetrafluoro-4,6-diiodobenzene (1/1) (2_eb843_a) top
Crystal data top
C8H6N4·C6F4I2F(000) = 1040
Mr = 560.03Dx = 2.330 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.4617 (10) ÅCell parameters from 6501 reflections
b = 6.4681 (6) Åθ = 2.8–27.1°
c = 23.966 (2) ŵ = 3.99 mm1
β = 100.069 (1)°T = 100 K
V = 1596.7 (3) Å3Cut, colourless
Z = 40.44 × 0.23 × 0.09 mm
Data collection top
Bruker APEXII CCD
diffractometer
3557 independent reflections
Radiation source: fine-focus sealed tube3283 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
Detector resolution: 8.3660 pixels mm-1θmax = 27.2°, θmin = 1.7°
phi and ω scansh = 1313
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
k = 88
Tmin = 0.345, Tmax = 0.699l = 3030
18558 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029H-atom parameters constrained
wR(F2) = 0.051 w = 1/[σ2(Fo2) + (0.0041P)2 + 4.730P]
where P = (Fo2 + 2Fc2)/3
S = 1.18(Δ/σ)max = 0.002
3557 reflectionsΔρmax = 0.94 e Å3
217 parametersΔρmin = 1.00 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
I10.37336 (2)0.38726 (4)0.71890 (2)0.01442 (6)
F10.5983 (2)0.2430 (3)0.65150 (9)0.0174 (5)
N10.2137 (3)0.2038 (5)0.79103 (13)0.0166 (7)
C10.1543 (4)0.3107 (6)0.82688 (15)0.0161 (8)
H10.1877150.4426450.8393140.019*
I20.73110 (2)0.35214 (4)0.54356 (2)0.01583 (7)
F20.6115 (2)0.8049 (3)0.52729 (9)0.0216 (5)
N20.0607 (3)0.0699 (5)0.79163 (13)0.0193 (7)
C20.1635 (4)0.0179 (6)0.77553 (16)0.0179 (8)
H20.2056550.0595750.7503680.022*
F30.4345 (2)1.0065 (3)0.57584 (9)0.0204 (5)
N30.1352 (3)0.3714 (5)0.96376 (13)0.0179 (7)
C30.0023 (4)0.0433 (6)0.82699 (16)0.0169 (8)
H30.0725450.0115480.8391220.020*
F40.3330 (2)0.8283 (3)0.65982 (9)0.0197 (5)
N40.0976 (3)0.6816 (5)0.91511 (14)0.0194 (7)
C40.0467 (4)0.2373 (6)0.84653 (15)0.0142 (7)
C50.0210 (4)0.3555 (6)0.88593 (15)0.0149 (7)
C60.0729 (4)0.2630 (6)0.92913 (15)0.0160 (8)
H60.0640190.1177980.9343570.019*
C70.1446 (4)0.5748 (6)0.95445 (17)0.0188 (8)
H70.1898140.6517750.9785910.023*
C80.0361 (4)0.5689 (6)0.88104 (16)0.0169 (8)
H80.0011930.6380650.8521160.020*
C90.4617 (3)0.5277 (5)0.65676 (14)0.0123 (7)
C100.5548 (4)0.4301 (5)0.63152 (15)0.0138 (7)
C110.6071 (3)0.5156 (6)0.58747 (15)0.0131 (7)
C120.5653 (4)0.7124 (6)0.57009 (14)0.0137 (7)
C130.4751 (4)0.8188 (5)0.59472 (15)0.0138 (7)
C140.4237 (4)0.7253 (6)0.63740 (15)0.0137 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.01711 (13)0.01538 (11)0.01217 (11)0.00043 (9)0.00645 (9)0.00128 (9)
F10.0226 (12)0.0133 (10)0.0180 (11)0.0042 (9)0.0086 (9)0.0033 (8)
N10.0183 (17)0.0186 (16)0.0136 (16)0.0012 (13)0.0049 (13)0.0032 (13)
C10.018 (2)0.0159 (18)0.0144 (18)0.0007 (15)0.0027 (15)0.0036 (14)
I20.01594 (13)0.01947 (12)0.01335 (12)0.00000 (10)0.00608 (9)0.00225 (9)
F20.0245 (13)0.0252 (12)0.0176 (11)0.0005 (10)0.0108 (10)0.0092 (9)
N20.0245 (19)0.0178 (16)0.0171 (16)0.0008 (14)0.0079 (14)0.0019 (13)
C20.020 (2)0.0200 (19)0.0137 (18)0.0027 (16)0.0029 (16)0.0023 (15)
F30.0257 (13)0.0146 (11)0.0200 (12)0.0031 (9)0.0018 (10)0.0065 (9)
N30.0175 (17)0.0220 (17)0.0159 (16)0.0015 (14)0.0080 (13)0.0027 (13)
C30.017 (2)0.0164 (18)0.0182 (19)0.0008 (15)0.0048 (16)0.0028 (15)
F40.0222 (12)0.0200 (11)0.0184 (11)0.0064 (9)0.0080 (9)0.0011 (9)
N40.0208 (18)0.0177 (16)0.0213 (17)0.0019 (13)0.0080 (14)0.0009 (13)
C40.0156 (19)0.0165 (18)0.0110 (17)0.0013 (15)0.0035 (15)0.0020 (14)
C50.0136 (18)0.0161 (18)0.0151 (17)0.0001 (15)0.0024 (14)0.0005 (15)
C60.018 (2)0.0158 (18)0.0148 (18)0.0011 (15)0.0050 (16)0.0033 (14)
C70.017 (2)0.0193 (19)0.021 (2)0.0026 (15)0.0070 (16)0.0028 (15)
C80.019 (2)0.0171 (18)0.0159 (19)0.0024 (15)0.0080 (16)0.0015 (14)
C90.0128 (18)0.0156 (17)0.0091 (17)0.0005 (14)0.0032 (14)0.0002 (13)
C100.0167 (19)0.0117 (17)0.0127 (17)0.0007 (14)0.0021 (14)0.0002 (14)
C110.0109 (18)0.0197 (18)0.0090 (17)0.0014 (14)0.0031 (14)0.0014 (14)
C120.0150 (19)0.0193 (18)0.0065 (16)0.0044 (15)0.0009 (14)0.0030 (13)
C130.0158 (19)0.0130 (17)0.0115 (17)0.0004 (14)0.0008 (15)0.0005 (13)
C140.0141 (19)0.0163 (18)0.0109 (17)0.0013 (14)0.0026 (14)0.0035 (14)
Geometric parameters (Å, º) top
I1—C92.092 (3)F4—C141.346 (4)
F1—C101.351 (4)N4—C71.331 (5)
N1—C11.337 (5)N4—C81.340 (5)
N1—C21.338 (5)C4—C51.487 (5)
C1—C41.379 (5)C5—C61.386 (5)
C1—H10.9500C5—C81.392 (5)
I2—C112.094 (4)C6—H60.9500
F2—C121.348 (4)C7—H70.9500
N2—C21.332 (5)C8—H80.9500
N2—C31.345 (5)C9—C101.386 (5)
C2—H20.9500C9—C141.394 (5)
F3—C131.339 (4)C10—C111.386 (5)
N3—C71.335 (5)C11—C121.386 (5)
N3—C61.339 (5)C12—C131.381 (5)
C3—C41.390 (5)C13—C141.376 (5)
C3—H30.9500
C1—N1—C2116.0 (3)N4—C7—H7116.4
N1—C1—C4122.7 (4)N3—C7—H7116.4
N1—C1—H1118.7N4—C8—C5123.2 (3)
C4—C1—H1118.7N4—C8—H8118.4
C2—N2—C3115.4 (3)C5—C8—H8118.4
N2—C2—N1126.9 (4)C10—C9—C14117.0 (3)
N2—C2—H2116.5C10—C9—I1123.0 (3)
N1—C2—H2116.5C14—C9—I1120.0 (3)
C7—N3—C6116.2 (3)F1—C10—C9118.2 (3)
N2—C3—C4122.8 (4)F1—C10—C11118.3 (3)
N2—C3—H3118.6C9—C10—C11123.5 (3)
C4—C3—H3118.6C10—C11—C12116.7 (3)
C7—N4—C8115.2 (3)C10—C11—I2122.9 (3)
C1—C4—C3116.1 (3)C12—C11—I2120.2 (3)
C1—C4—C5123.2 (3)F2—C12—C13117.8 (3)
C3—C4—C5120.7 (3)F2—C12—C11120.0 (3)
C6—C5—C8115.9 (3)C13—C12—C11122.2 (3)
C6—C5—C4123.0 (3)F3—C13—C14120.5 (3)
C8—C5—C4121.1 (3)F3—C13—C12120.5 (3)
N3—C6—C5122.3 (3)C14—C13—C12118.9 (3)
N3—C6—H6118.9F4—C14—C13118.3 (3)
C5—C6—H6118.9F4—C14—C9120.1 (3)
N4—C7—N3127.2 (4)C13—C14—C9121.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···I1i0.953.284.020 (4)137
C7—H7···F2ii0.952.573.424 (4)150
C8—H8···N2iii0.952.533.440 (5)160
Symmetry codes: (i) x, y1/2, z+3/2; (ii) x1, y+3/2, z+1/2; (iii) x, y+1, z.
5-{[4-(Dimethylamino)phenyl]ethynyl}pyrimidine–1,2,3,5-tetrafluoro-4,6-diiodobenzene (1/1) (3_eb797_a) top
Crystal data top
C14H13N3·C6F4I2F(000) = 592
Mr = 625.13Dx = 1.943 Mg m3
Monoclinic, P21/mMo Kα radiation, λ = 0.71073 Å
a = 6.9939 (5) ÅCell parameters from 9430 reflections
b = 13.640 (1) Åθ = 2.4–27.1°
c = 11.2299 (8) ŵ = 2.99 mm1
β = 94.260 (1)°T = 100 K
V = 1068.34 (13) Å3Cut BLOCK, colourless
Z = 20.25 × 0.20 × 0.10 mm
Data collection top
Bruker APEXII CCD
diffractometer
2445 independent reflections
Radiation source: fine-focus sealed tube2326 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.015
Detector resolution: 8.3660 pixels mm-1θmax = 27.1°, θmin = 1.8°
phi and ω scansh = 88
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
k = 1717
Tmin = 0.493, Tmax = 0.742l = 1414
13568 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.018H-atom parameters constrained
wR(F2) = 0.043 w = 1/[σ2(Fo2) + (0.0209P)2 + 1.2801P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
2445 reflectionsΔρmax = 1.12 e Å3
149 parametersΔρmin = 0.56 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
I10.17202 (2)0.52669 (2)0.69662 (2)0.02063 (5)
F10.2034 (2)0.7500000.61207 (14)0.0201 (3)
N10.2135 (2)0.33712 (12)0.58048 (15)0.0211 (3)
C10.1924 (4)0.2500000.6314 (2)0.0208 (5)
H10.1589630.2500000.7118350.025*
F20.06563 (19)0.57924 (9)0.96021 (11)0.0286 (3)
N20.6266 (4)0.2500000.2843 (2)0.0227 (5)
C20.2628 (3)0.33650 (15)0.46776 (18)0.0217 (4)
H20.2801770.3973420.4288370.026*
F30.0162 (3)0.7500001.07364 (15)0.0267 (4)
C30.2895 (4)0.2500000.4052 (2)0.0192 (5)
C40.3387 (4)0.2500000.2838 (3)0.0245 (6)
C50.3753 (4)0.2500000.1819 (3)0.0246 (6)
C60.4261 (4)0.2500000.0604 (3)0.0226 (6)
C70.4557 (3)0.33794 (16)0.00044 (18)0.0244 (4)
H70.4312260.3984290.0383980.029*
C80.5200 (3)0.33845 (16)0.11335 (18)0.0234 (4)
H80.5388340.3991880.1522020.028*
C90.5579 (4)0.2500000.1722 (2)0.0204 (5)
C100.7009 (3)0.34144 (17)0.32998 (19)0.0275 (5)
H10A0.5982520.3904770.3368680.041*
H10B0.7483420.3299230.4087220.041*
H10C0.8059900.3653510.2750030.041*
C110.1585 (4)0.7500000.7276 (2)0.0157 (5)
C120.1363 (3)0.66066 (13)0.78312 (17)0.0165 (4)
C130.0885 (3)0.66292 (14)0.90066 (17)0.0184 (4)
C140.0633 (4)0.7500000.9597 (2)0.0187 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.02501 (8)0.01135 (7)0.02520 (8)0.00111 (4)0.00041 (5)0.00193 (4)
F10.0264 (8)0.0196 (8)0.0147 (7)0.0000.0038 (6)0.000
N10.0236 (8)0.0166 (8)0.0229 (8)0.0024 (6)0.0003 (6)0.0022 (6)
C10.0213 (13)0.0242 (14)0.0166 (13)0.0000.0005 (10)0.000
F20.0399 (7)0.0196 (6)0.0267 (6)0.0059 (5)0.0056 (5)0.0085 (5)
N20.0237 (12)0.0239 (13)0.0208 (12)0.0000.0036 (9)0.000
C20.0221 (9)0.0185 (10)0.0242 (10)0.0003 (8)0.0003 (7)0.0050 (8)
F30.0274 (9)0.0356 (10)0.0178 (8)0.0000.0066 (7)0.000
C30.0144 (12)0.0252 (14)0.0179 (13)0.0000.0000 (10)0.000
C40.0172 (13)0.0325 (17)0.0234 (15)0.0000.0007 (11)0.000
C50.0154 (13)0.0347 (16)0.0234 (15)0.0000.0006 (10)0.000
C60.0143 (12)0.0347 (16)0.0189 (13)0.0000.0022 (10)0.000
C70.0218 (10)0.0274 (11)0.0239 (10)0.0042 (8)0.0005 (8)0.0035 (8)
C80.0218 (9)0.0258 (10)0.0224 (10)0.0033 (8)0.0003 (7)0.0015 (8)
C90.0150 (12)0.0276 (15)0.0184 (13)0.0000.0000 (10)0.000
C100.0307 (11)0.0282 (11)0.0246 (10)0.0037 (9)0.0072 (8)0.0018 (9)
C110.0167 (12)0.0154 (12)0.0151 (11)0.0000.0014 (9)0.000
C120.0176 (8)0.0116 (8)0.0202 (9)0.0003 (7)0.0001 (7)0.0012 (7)
C130.0195 (9)0.0159 (9)0.0199 (9)0.0021 (7)0.0018 (7)0.0044 (7)
C140.0163 (12)0.0235 (14)0.0168 (12)0.0000.0035 (10)0.000
Geometric parameters (Å, º) top
I1—C122.0932 (18)C5—C61.436 (4)
F1—C111.357 (3)C6—C7i1.398 (3)
N1—C11.332 (2)C6—C71.398 (3)
N1—C21.336 (3)C7—C81.386 (3)
C1—H10.9500C7—H70.9500
F2—C131.338 (2)C8—C91.410 (3)
N2—C91.380 (4)C8—H80.9500
N2—C10i1.459 (2)C10—H10A0.9800
N2—C101.459 (2)C10—H10B0.9800
C2—C31.393 (2)C10—H10C0.9800
C2—H20.9500C11—C12ii1.383 (2)
F3—C141.345 (3)C11—C121.383 (2)
C3—C41.430 (4)C12—C131.386 (3)
C4—C51.191 (4)C13—C141.378 (2)
C1—N1—C2116.46 (18)C9—C8—H8119.6
N1i—C1—N1126.4 (3)N2—C9—C8i121.18 (13)
N1i—C1—H1116.8N2—C9—C8121.18 (13)
N1—C1—H1116.8C8i—C9—C8117.6 (3)
C9—N2—C10i118.53 (13)N2—C10—H10A109.5
C9—N2—C10118.53 (13)N2—C10—H10B109.5
C10i—N2—C10117.5 (2)H10A—C10—H10B109.5
N1—C2—C3122.47 (19)N2—C10—H10C109.5
N1—C2—H2118.8H10A—C10—H10C109.5
C3—C2—H2118.8H10B—C10—H10C109.5
C2—C3—C2i115.8 (2)F1—C11—C12ii118.21 (12)
C2—C3—C4122.11 (12)F1—C11—C12118.21 (12)
C2i—C3—C4122.11 (12)C12ii—C11—C12123.6 (2)
C5—C4—C3178.5 (3)C11—C12—C13116.94 (18)
C4—C5—C6178.1 (3)C11—C12—I1122.60 (15)
C7i—C6—C7118.1 (3)C13—C12—I1120.47 (14)
C7i—C6—C5120.90 (13)F2—C13—C14118.06 (17)
C7—C6—C5120.90 (13)F2—C13—C12120.21 (17)
C8—C7—C6121.2 (2)C14—C13—C12121.73 (18)
C8—C7—H7119.4F3—C14—C13120.45 (12)
C6—C7—H7119.4F3—C14—C13ii120.45 (12)
C7—C8—C9120.9 (2)C13—C14—C13ii119.1 (2)
C7—C8—H8119.6
Symmetry codes: (i) x, y+1/2, z; (ii) x, y+3/2, z.
2-{[4-(Dimethylamino)phenyl]ethynyl}pyrimidine–1,2,3,5-tetrafluoro-4,6-diiodobenzene (1/1) (4_eb814_a) top
Crystal data top
2C14H13N3·2C6F4I2Z = 2
Mr = 1250.27F(000) = 1184
Triclinic, P1Dx = 1.978 Mg m3
a = 9.1740 (7) ÅMo Kα radiation, λ = 0.71073 Å
b = 14.0178 (10) ÅCell parameters from 9917 reflections
c = 17.5605 (13) Åθ = 2.4–27.1°
α = 100.065 (1)°µ = 3.04 mm1
β = 95.285 (1)°T = 100 K
γ = 107.225 (1)°Cut, colourless
V = 2098.8 (3) Å30.50 × 0.27 × 0.17 mm
Data collection top
Bruker APEXII CCD
diffractometer
9224 independent reflections
Radiation source: fine-focus sealed tube8375 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
Detector resolution: 8.3660 pixels mm-1θmax = 27.1°, θmin = 1.6°
phi and ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
k = 1717
Tmin = 0.394, Tmax = 0.589l = 2222
26355 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.021H-atom parameters constrained
wR(F2) = 0.050 w = 1/[σ2(Fo2) + (0.0241P)2 + 0.6867P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.003
9224 reflectionsΔρmax = 0.99 e Å3
527 parametersΔρmin = 0.46 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
I10.01383 (2)0.28785 (2)0.05480 (2)0.01866 (4)
F10.29851 (17)0.16750 (12)0.06022 (8)0.0234 (3)
N10.3243 (2)0.34365 (15)0.01771 (12)0.0166 (4)
C10.3477 (3)0.31927 (18)0.05610 (14)0.0186 (5)
H10.2611440.2818680.0951030.022*
I20.65899 (2)0.05764 (2)0.07293 (2)0.01721 (4)
F20.66975 (16)0.13500 (12)0.11002 (9)0.0262 (3)
N20.5967 (2)0.42626 (16)0.05520 (12)0.0175 (4)
C20.4932 (3)0.34632 (19)0.07814 (15)0.0192 (5)
H20.5080720.3284170.1309080.023*
I30.85764 (2)0.54755 (2)0.17666 (2)0.01709 (4)
F30.44678 (17)0.24057 (12)0.23158 (8)0.0257 (3)
N30.3471 (2)0.59644 (17)0.52730 (12)0.0201 (5)
C30.6155 (3)0.40069 (19)0.01934 (15)0.0195 (5)
H30.7168490.4206280.0324220.023*
I41.12375 (2)0.78072 (2)0.51038 (2)0.01727 (4)
F40.14869 (17)0.30235 (11)0.21104 (8)0.0223 (3)
N41.0435 (2)0.83658 (16)0.66195 (12)0.0191 (4)
C40.4508 (3)0.39684 (18)0.07058 (14)0.0151 (5)
F50.88976 (15)0.65121 (11)0.35745 (8)0.0197 (3)
N51.1087 (2)0.92578 (16)0.79570 (12)0.0176 (4)
C50.4270 (3)0.42633 (19)0.14981 (14)0.0182 (5)
F61.42714 (16)0.81466 (11)0.42497 (9)0.0243 (3)
N62.0672 (2)1.09674 (17)0.67626 (13)0.0225 (5)
C60.4048 (3)0.45375 (19)0.21490 (15)0.0181 (5)
F71.46342 (16)0.75035 (13)0.27629 (9)0.0300 (4)
C70.3872 (3)0.48979 (19)0.29340 (14)0.0171 (5)
F81.21991 (17)0.63395 (13)0.16906 (9)0.0295 (4)
C80.2453 (3)0.45855 (19)0.32093 (15)0.0182 (5)
H80.1568800.4133560.2861010.022*
C90.2326 (3)0.49255 (19)0.39781 (15)0.0174 (5)
H90.1357320.4694170.4151930.021*
C100.3607 (3)0.56111 (18)0.45137 (14)0.0163 (5)
C110.5024 (3)0.59344 (19)0.42259 (14)0.0170 (5)
H110.5904620.6404730.4566260.020*
C120.5146 (3)0.55782 (19)0.34612 (15)0.0189 (5)
H120.6115770.5798360.3286220.023*
C130.2122 (3)0.5466 (2)0.56038 (16)0.0247 (6)
H13A0.1225330.5626520.5381630.037*
H13B0.2314710.5711210.6173170.037*
H13C0.1916800.4724560.5479220.037*
C140.4766 (3)0.6724 (2)0.57970 (16)0.0261 (6)
H14A0.5557270.6413020.5926970.039*
H14B0.4414340.6983600.6277270.039*
H14C0.5203420.7289650.5541200.039*
C150.2167 (3)0.23794 (18)0.07389 (14)0.0167 (5)
C160.3351 (3)0.18531 (18)0.01254 (14)0.0166 (5)
C170.4891 (3)0.14794 (18)0.02118 (14)0.0169 (5)
C180.5228 (3)0.16846 (19)0.09641 (15)0.0187 (5)
C190.4097 (3)0.22148 (19)0.15931 (14)0.0181 (5)
C200.2573 (3)0.25419 (18)0.14763 (14)0.0175 (5)
C211.0472 (3)0.63818 (18)0.26077 (14)0.0157 (5)
C221.0333 (3)0.67444 (18)0.33750 (14)0.0146 (5)
C231.1557 (3)0.73286 (18)0.39466 (14)0.0161 (5)
C241.3013 (3)0.75763 (19)0.37278 (15)0.0181 (5)
C251.3215 (3)0.7243 (2)0.29693 (15)0.0207 (5)
C261.1958 (3)0.66498 (19)0.24240 (15)0.0189 (5)
C270.8960 (3)0.80064 (19)0.67321 (15)0.0205 (5)
H270.8213000.7573050.6303980.025*
C280.8489 (3)0.82401 (19)0.74399 (15)0.0206 (5)
H280.7443050.7972650.7511600.025*
C290.9611 (3)0.88851 (19)0.80456 (15)0.0198 (5)
H290.9318910.9068480.8541690.024*
C301.1437 (3)0.89742 (18)0.72425 (14)0.0154 (5)
C311.3025 (3)0.93454 (19)0.71349 (15)0.0189 (5)
C321.4343 (3)0.96259 (19)0.70317 (15)0.0189 (5)
C331.5941 (3)0.99660 (18)0.69455 (15)0.0180 (5)
C341.7046 (3)1.05532 (19)0.75934 (15)0.0192 (5)
H341.6721901.0719760.8083920.023*
C351.8596 (3)1.08942 (19)0.75311 (15)0.0188 (5)
H351.9318281.1297480.7978430.023*
C361.9126 (3)1.06565 (18)0.68200 (14)0.0163 (5)
C371.8002 (3)1.00715 (18)0.61632 (14)0.0172 (5)
H371.8318280.9904580.5670900.021*
C381.6458 (3)0.97431 (18)0.62308 (14)0.0174 (5)
H381.5726750.9356400.5782100.021*
C392.1782 (3)1.1623 (2)0.74254 (17)0.0272 (6)
H39A2.1602721.2284080.7547270.041*
H39B2.2829071.1725740.7298950.041*
H39C2.1668611.1302200.7879200.041*
C402.1221 (3)1.0737 (2)0.60229 (15)0.0224 (6)
H40A2.0837570.9997160.5813630.034*
H40B2.2352921.0971430.6107350.034*
H40C2.0843471.1085840.5649570.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.01293 (8)0.02075 (9)0.01951 (9)0.00233 (6)0.00128 (6)0.00298 (6)
F10.0202 (8)0.0313 (9)0.0134 (7)0.0035 (7)0.0040 (6)0.0016 (6)
N10.0149 (10)0.0174 (10)0.0158 (10)0.0043 (8)0.0001 (8)0.0019 (8)
C10.0213 (13)0.0164 (12)0.0156 (12)0.0052 (10)0.0023 (10)0.0009 (10)
I20.01488 (8)0.01587 (8)0.01746 (8)0.00258 (6)0.00194 (6)0.00105 (6)
F20.0133 (7)0.0376 (9)0.0244 (8)0.0036 (7)0.0062 (6)0.0040 (7)
N20.0157 (10)0.0169 (10)0.0170 (11)0.0029 (8)0.0022 (8)0.0002 (8)
C20.0251 (14)0.0181 (12)0.0143 (12)0.0068 (10)0.0045 (10)0.0024 (10)
I30.01489 (8)0.01655 (8)0.01638 (8)0.00303 (6)0.00064 (6)0.00043 (6)
F30.0270 (8)0.0372 (9)0.0140 (8)0.0119 (7)0.0066 (6)0.0036 (7)
N30.0169 (11)0.0270 (12)0.0135 (10)0.0047 (9)0.0037 (8)0.0002 (9)
C30.0176 (13)0.0195 (13)0.0204 (13)0.0036 (10)0.0060 (10)0.0036 (10)
I40.01797 (8)0.01846 (8)0.01424 (8)0.00583 (6)0.00058 (6)0.00149 (6)
F40.0208 (8)0.0262 (8)0.0152 (7)0.0050 (6)0.0044 (6)0.0004 (6)
N40.0159 (11)0.0202 (11)0.0180 (11)0.0023 (9)0.0020 (8)0.0023 (9)
C40.0171 (12)0.0132 (11)0.0135 (12)0.0032 (9)0.0007 (9)0.0024 (9)
F50.0110 (7)0.0281 (8)0.0176 (7)0.0027 (6)0.0046 (6)0.0032 (6)
N50.0154 (10)0.0189 (11)0.0165 (11)0.0029 (8)0.0026 (8)0.0033 (8)
C50.0148 (12)0.0207 (13)0.0167 (13)0.0042 (10)0.0002 (10)0.0015 (10)
F60.0137 (7)0.0272 (8)0.0230 (8)0.0011 (6)0.0039 (6)0.0016 (7)
N60.0136 (11)0.0278 (12)0.0200 (11)0.0009 (9)0.0053 (9)0.0015 (9)
C60.0143 (12)0.0195 (13)0.0198 (13)0.0050 (10)0.0009 (10)0.0039 (10)
F70.0116 (7)0.0431 (10)0.0305 (9)0.0023 (7)0.0089 (7)0.0032 (8)
C70.0174 (12)0.0181 (12)0.0152 (12)0.0060 (10)0.0019 (10)0.0014 (10)
F80.0210 (8)0.0424 (10)0.0193 (8)0.0057 (7)0.0064 (6)0.0025 (7)
C80.0121 (12)0.0176 (12)0.0203 (13)0.0011 (10)0.0017 (10)0.0010 (10)
C90.0118 (11)0.0219 (13)0.0180 (12)0.0038 (10)0.0037 (9)0.0048 (10)
C100.0177 (12)0.0166 (12)0.0153 (12)0.0078 (10)0.0019 (10)0.0011 (10)
C110.0122 (11)0.0200 (12)0.0154 (12)0.0021 (10)0.0006 (9)0.0014 (10)
C120.0113 (11)0.0244 (13)0.0193 (13)0.0043 (10)0.0017 (10)0.0031 (11)
C130.0249 (14)0.0300 (15)0.0204 (14)0.0088 (12)0.0084 (11)0.0060 (11)
C140.0235 (14)0.0307 (15)0.0175 (13)0.0042 (12)0.0002 (11)0.0029 (11)
C150.0142 (12)0.0167 (12)0.0187 (12)0.0042 (10)0.0027 (10)0.0038 (10)
C160.0178 (12)0.0169 (12)0.0142 (12)0.0042 (10)0.0023 (10)0.0032 (10)
C170.0174 (12)0.0160 (12)0.0156 (12)0.0055 (10)0.0019 (10)0.0008 (10)
C180.0137 (12)0.0216 (13)0.0220 (13)0.0061 (10)0.0050 (10)0.0058 (11)
C190.0208 (13)0.0225 (13)0.0128 (12)0.0086 (11)0.0048 (10)0.0036 (10)
C200.0168 (12)0.0175 (12)0.0155 (12)0.0049 (10)0.0041 (10)0.0008 (10)
C210.0134 (11)0.0174 (12)0.0148 (12)0.0037 (10)0.0001 (9)0.0027 (10)
C220.0097 (11)0.0167 (12)0.0167 (12)0.0026 (9)0.0018 (9)0.0048 (10)
C230.0156 (12)0.0167 (12)0.0153 (12)0.0043 (10)0.0022 (9)0.0028 (10)
C240.0117 (11)0.0178 (12)0.0203 (13)0.0009 (10)0.0035 (10)0.0015 (10)
C250.0121 (12)0.0238 (13)0.0249 (14)0.0029 (10)0.0062 (10)0.0053 (11)
C260.0170 (12)0.0230 (13)0.0164 (12)0.0067 (10)0.0050 (10)0.0018 (10)
C270.0144 (12)0.0211 (13)0.0207 (13)0.0001 (10)0.0013 (10)0.0023 (11)
C280.0122 (12)0.0228 (13)0.0245 (14)0.0015 (10)0.0029 (10)0.0062 (11)
C290.0197 (13)0.0216 (13)0.0185 (13)0.0057 (11)0.0062 (10)0.0049 (10)
C300.0140 (12)0.0156 (12)0.0153 (12)0.0026 (9)0.0014 (9)0.0038 (9)
C310.0165 (13)0.0203 (13)0.0167 (12)0.0028 (10)0.0011 (10)0.0016 (10)
C320.0171 (13)0.0178 (12)0.0184 (13)0.0022 (10)0.0005 (10)0.0024 (10)
C330.0173 (12)0.0164 (12)0.0193 (13)0.0034 (10)0.0042 (10)0.0039 (10)
C340.0185 (13)0.0227 (13)0.0147 (12)0.0054 (10)0.0040 (10)0.0008 (10)
C350.0168 (12)0.0200 (13)0.0155 (12)0.0024 (10)0.0010 (10)0.0003 (10)
C360.0136 (12)0.0148 (12)0.0190 (12)0.0018 (9)0.0027 (10)0.0043 (10)
C370.0185 (12)0.0179 (12)0.0146 (12)0.0055 (10)0.0037 (10)0.0020 (10)
C380.0157 (12)0.0164 (12)0.0164 (12)0.0016 (10)0.0010 (10)0.0020 (10)
C390.0140 (13)0.0300 (15)0.0283 (15)0.0002 (11)0.0015 (11)0.0047 (12)
C400.0165 (13)0.0295 (15)0.0239 (14)0.0083 (11)0.0078 (11)0.0085 (11)
Geometric parameters (Å, º) top
I1—C152.101 (2)C12—H120.9500
F1—C161.351 (3)C13—H13A0.9800
N1—C11.335 (3)C13—H13B0.9800
N1—C41.346 (3)C13—H13C0.9800
C1—C21.386 (4)C14—H14A0.9800
C1—H10.9500C14—H14B0.9800
I2—C172.095 (2)C14—H14C0.9800
F2—C181.349 (3)C15—C201.380 (3)
N2—C31.336 (3)C15—C161.384 (3)
N2—C41.346 (3)C16—C171.386 (3)
C2—C31.383 (4)C17—C181.385 (3)
C2—H20.9500C18—C191.376 (4)
I3—C212.094 (2)C19—C201.383 (3)
F3—C191.346 (3)C21—C221.386 (3)
N3—C101.369 (3)C21—C261.387 (3)
N3—C141.449 (3)C22—C231.378 (3)
N3—C131.456 (3)C23—C241.385 (3)
C3—H30.9500C24—C251.381 (4)
I4—C232.101 (2)C25—C261.374 (4)
F4—C201.350 (3)C27—C281.371 (4)
N4—C301.339 (3)C27—H270.9500
N4—C271.344 (3)C28—C291.386 (4)
C4—C51.436 (3)C28—H280.9500
F5—C221.354 (3)C29—H290.9500
N5—C291.334 (3)C30—C311.437 (3)
N5—C301.346 (3)C31—C321.196 (3)
C5—C61.196 (3)C32—C331.433 (3)
F6—C241.347 (3)C33—C381.399 (3)
N6—C361.373 (3)C33—C341.402 (3)
N6—C391.446 (3)C34—C351.382 (3)
N6—C401.455 (3)C34—H340.9500
C6—C71.424 (3)C35—C361.403 (3)
F7—C251.346 (3)C35—H350.9500
C7—C121.401 (3)C36—C371.420 (3)
C7—C81.404 (3)C37—C381.377 (3)
F8—C261.345 (3)C37—H370.9500
C8—C91.378 (3)C38—H380.9500
C8—H80.9500C39—H39A0.9800
C9—C101.414 (3)C39—H39B0.9800
C9—H90.9500C39—H39C0.9800
C10—C111.415 (3)C40—H40A0.9800
C11—C121.375 (3)C40—H40B0.9800
C11—H110.9500C40—H40C0.9800
C1—N1—C4116.2 (2)F3—C19—C20120.3 (2)
N1—C1—C2122.7 (2)C18—C19—C20119.3 (2)
N1—C1—H1118.7F4—C20—C15120.8 (2)
C2—C1—H1118.7F4—C20—C19117.8 (2)
C3—N2—C4116.4 (2)C15—C20—C19121.4 (2)
C3—C2—C1116.5 (2)C22—C21—C26116.0 (2)
C3—C2—H2121.7C22—C21—I3122.78 (17)
C1—C2—H2121.7C26—C21—I3121.25 (18)
C10—N3—C14120.6 (2)F5—C22—C23117.9 (2)
C10—N3—C13120.4 (2)F5—C22—C21117.7 (2)
C14—N3—C13118.3 (2)C23—C22—C21124.3 (2)
N2—C3—C2122.5 (2)C22—C23—C24117.1 (2)
N2—C3—H3118.8C22—C23—I4121.55 (17)
C2—C3—H3118.8C24—C23—I4121.33 (18)
C30—N4—C27116.1 (2)F6—C24—C25118.2 (2)
N1—C4—N2125.6 (2)F6—C24—C23120.9 (2)
N1—C4—C5116.9 (2)C25—C24—C23120.9 (2)
N2—C4—C5117.5 (2)F7—C25—C26120.1 (2)
C29—N5—C30116.3 (2)F7—C25—C24120.2 (2)
C6—C5—C4177.4 (3)C26—C25—C24119.7 (2)
C36—N6—C39120.1 (2)F8—C26—C25118.0 (2)
C36—N6—C40121.5 (2)F8—C26—C21120.0 (2)
C39—N6—C40118.1 (2)C25—C26—C21122.0 (2)
C5—C6—C7176.8 (3)N4—C27—C28122.6 (2)
C12—C7—C8118.0 (2)N4—C27—H27118.7
C12—C7—C6119.9 (2)C28—C27—H27118.7
C8—C7—C6122.2 (2)C27—C28—C29116.8 (2)
C9—C8—C7120.9 (2)C27—C28—H28121.6
C9—C8—H8119.5C29—C28—H28121.6
C7—C8—H8119.5N5—C29—C28122.4 (2)
C8—C9—C10121.5 (2)N5—C29—H29118.8
C8—C9—H9119.3C28—C29—H29118.8
C10—C9—H9119.3N4—C30—N5125.8 (2)
N3—C10—C9121.4 (2)N4—C30—C31116.7 (2)
N3—C10—C11121.5 (2)N5—C30—C31117.6 (2)
C9—C10—C11117.1 (2)C32—C31—C30178.0 (3)
C12—C11—C10121.0 (2)C31—C32—C33177.4 (3)
C12—C11—H11119.5C38—C33—C34117.9 (2)
C10—C11—H11119.5C38—C33—C32122.5 (2)
C11—C12—C7121.5 (2)C34—C33—C32119.6 (2)
C11—C12—H12119.2C35—C34—C33121.1 (2)
C7—C12—H12119.2C35—C34—H34119.4
N3—C13—H13A109.5C33—C34—H34119.4
N3—C13—H13B109.5C34—C35—C36121.3 (2)
H13A—C13—H13B109.5C34—C35—H35119.4
N3—C13—H13C109.5C36—C35—H35119.4
H13A—C13—H13C109.5N6—C36—C35121.4 (2)
H13B—C13—H13C109.5N6—C36—C37121.3 (2)
N3—C14—H14A109.5C35—C36—C37117.3 (2)
N3—C14—H14B109.5C38—C37—C36120.8 (2)
H14A—C14—H14B109.5C38—C37—H37119.6
N3—C14—H14C109.5C36—C37—H37119.6
H14A—C14—H14C109.5C37—C38—C33121.5 (2)
H14B—C14—H14C109.5C37—C38—H38119.3
C20—C15—C16116.9 (2)C33—C38—H38119.3
C20—C15—I1122.01 (18)N6—C39—H39A109.5
C16—C15—I1121.06 (18)N6—C39—H39B109.5
F1—C16—C15118.2 (2)H39A—C39—H39B109.5
F1—C16—C17117.7 (2)N6—C39—H39C109.5
C15—C16—C17124.1 (2)H39A—C39—H39C109.5
C18—C17—C16116.2 (2)H39B—C39—H39C109.5
C18—C17—I2121.82 (18)N6—C40—H40A109.5
C16—C17—I2121.83 (18)N6—C40—H40B109.5
F2—C18—C19117.9 (2)H40A—C40—H40B109.5
F2—C18—C17120.1 (2)N6—C40—H40C109.5
C19—C18—C17122.0 (2)H40A—C40—H40C109.5
F3—C19—C18120.4 (2)H40B—C40—H40C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···F8i0.952.573.170 (3)121
C3—H3···F8i0.952.563.185 (3)124
C13—H13A···I4ii0.983.183.828 (3)125
C13—H13C···F5iii0.982.613.280 (3)126
C14—H14B···F3iv0.982.463.391 (3)158
C29—H29···F2iv0.952.473.145 (3)128
C39—H39A···I3v0.983.224.187 (3)170
C39—H39B···F7vi0.982.283.221 (3)161
C39—H39C···I2vii0.983.274.117 (3)146
C40—H40A···I4viii0.983.244.146 (3)154
C40—H40C···I4v0.983.134.060 (3)159
Symmetry codes: (i) x+2, y+1, z; (ii) x1, y, z; (iii) x+1, y+1, z+1; (iv) x, y+1, z+1; (v) x+3, y+2, z+1; (vi) x+4, y+2, z+1; (vii) x+3, y+1, z+1; (viii) x+1, y, z.
5-{[4-(Dimethylamino)phenyl]ethynyl}pyrimidine–1,2,3,4-tetrafluoro-5,6-diiodobenzene (1/1) (5_eb948_a) top
Crystal data top
C14H13N3·C6F4I2Z = 2
Mr = 625.13F(000) = 592
Triclinic, P1Dx = 1.957 Mg m3
a = 9.3688 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.4346 (7) ÅCell parameters from 9177 reflections
c = 12.0797 (7) Åθ = 2.3–27.1°
α = 62.075 (1)°µ = 3.01 mm1
β = 82.310 (1)°T = 100 K
γ = 68.234 (1)°Cut, colourless
V = 1060.63 (11) Å30.38 × 0.18 × 0.10 mm
Data collection top
Bruker APEXII CCD
diffractometer
4679 independent reflections
Radiation source: fine-focus sealed tube4312 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
Detector resolution: 8.3660 pixels mm-1θmax = 27.1°, θmin = 1.9°
phi and ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
k = 1414
Tmin = 0.527, Tmax = 0.740l = 1515
13784 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.020H-atom parameters constrained
wR(F2) = 0.046 w = 1/[σ2(Fo2) + (0.0193P)2 + 1.2644P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.003
4679 reflectionsΔρmax = 1.44 e Å3
264 parametersΔρmin = 0.61 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
I10.22187 (2)1.06411 (2)0.72486 (2)0.01787 (5)
F10.17435 (16)1.58998 (14)0.64783 (13)0.0235 (3)
N10.4842 (2)0.8055 (2)0.84647 (19)0.0209 (4)
C10.5097 (3)0.6930 (2)0.8286 (2)0.0203 (5)
H10.4472730.7019090.7672670.024*
I20.12511 (2)1.35300 (2)0.81081 (2)0.01766 (5)
F20.36196 (17)1.60429 (15)0.49033 (14)0.0305 (3)
N20.6888 (2)0.6694 (2)1.00246 (19)0.0210 (4)
C20.5751 (3)0.7878 (2)0.9331 (2)0.0214 (5)
H20.5571000.8672990.9467770.026*
F30.29595 (17)1.38803 (16)0.43050 (13)0.0287 (3)
N30.7907 (2)0.0955 (2)0.72789 (19)0.0208 (4)
C30.7120 (3)0.5580 (2)0.9832 (2)0.0210 (5)
H30.7921260.4717801.0310130.025*
F40.04156 (16)1.15776 (15)0.53062 (13)0.0241 (3)
C40.6238 (3)0.5630 (2)0.8961 (2)0.0176 (4)
C50.6472 (3)0.4423 (2)0.8780 (2)0.0199 (5)
C60.6648 (3)0.3425 (2)0.8616 (2)0.0190 (4)
C70.6900 (3)0.2267 (2)0.8354 (2)0.0177 (4)
C80.8143 (3)0.1001 (2)0.8922 (2)0.0195 (5)
H80.8774070.0873260.9552210.023*
C90.8473 (3)0.0068 (2)0.8584 (2)0.0188 (4)
H90.9321240.0919790.8986320.023*
C100.7563 (3)0.0091 (2)0.7647 (2)0.0177 (4)
C110.6279 (3)0.1343 (2)0.7116 (2)0.0191 (4)
H110.5623140.1462210.6506160.023*
C120.5955 (3)0.2405 (2)0.7466 (2)0.0194 (5)
H120.5077480.3239020.7097230.023*
C130.9382 (3)0.2114 (3)0.7686 (3)0.0268 (5)
H13A1.0217500.1736460.7375470.040*
H13B0.9453870.2765900.7351050.040*
H13C0.9467710.2620870.8604180.040*
C140.7166 (3)0.0627 (3)0.6131 (2)0.0260 (5)
H14A0.6049160.0340840.6210280.039*
H14B0.7537060.1465150.5988640.039*
H14C0.7414680.0146730.5421110.039*
C150.0283 (2)1.2500 (2)0.6468 (2)0.0164 (4)
C160.0068 (3)1.3611 (2)0.6781 (2)0.0165 (4)
C170.1368 (3)1.4791 (2)0.6224 (2)0.0177 (4)
C180.2346 (3)1.4895 (2)0.5400 (2)0.0206 (5)
C190.2006 (3)1.3799 (3)0.5095 (2)0.0209 (5)
C200.0697 (3)1.2625 (2)0.5627 (2)0.0189 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.01696 (8)0.01741 (8)0.01916 (8)0.00427 (6)0.00035 (5)0.00947 (6)
F10.0265 (7)0.0156 (6)0.0248 (7)0.0044 (6)0.0007 (6)0.0086 (6)
N10.0224 (10)0.0165 (9)0.0227 (10)0.0055 (8)0.0008 (8)0.0089 (8)
C10.0224 (12)0.0218 (11)0.0188 (11)0.0079 (9)0.0012 (9)0.0102 (9)
I20.02004 (8)0.01798 (8)0.01638 (8)0.00698 (6)0.00079 (5)0.00828 (6)
F20.0247 (8)0.0243 (7)0.0300 (8)0.0004 (6)0.0102 (6)0.0065 (6)
N20.0235 (10)0.0218 (10)0.0218 (10)0.0096 (8)0.0008 (8)0.0118 (8)
C20.0241 (12)0.0192 (11)0.0261 (12)0.0104 (10)0.0060 (10)0.0134 (10)
F30.0273 (8)0.0361 (8)0.0236 (7)0.0131 (7)0.0075 (6)0.0105 (6)
N30.0242 (10)0.0177 (9)0.0206 (10)0.0050 (8)0.0006 (8)0.0101 (8)
C30.0199 (11)0.0191 (11)0.0221 (11)0.0046 (9)0.0008 (9)0.0092 (9)
F40.0252 (7)0.0291 (8)0.0262 (7)0.0099 (6)0.0007 (6)0.0184 (6)
C40.0196 (11)0.0186 (11)0.0182 (11)0.0084 (9)0.0054 (9)0.0111 (9)
C50.0193 (11)0.0208 (11)0.0205 (11)0.0064 (9)0.0031 (9)0.0112 (9)
C60.0187 (11)0.0212 (11)0.0157 (10)0.0075 (9)0.0027 (8)0.0075 (9)
C70.0186 (11)0.0183 (11)0.0176 (11)0.0074 (9)0.0051 (9)0.0097 (9)
C80.0206 (11)0.0208 (11)0.0174 (11)0.0084 (9)0.0017 (9)0.0075 (9)
C90.0174 (11)0.0145 (10)0.0201 (11)0.0027 (9)0.0009 (9)0.0061 (9)
C100.0199 (11)0.0164 (10)0.0176 (10)0.0089 (9)0.0042 (9)0.0073 (9)
C110.0189 (11)0.0195 (11)0.0189 (11)0.0057 (9)0.0034 (9)0.0085 (9)
C120.0178 (11)0.0155 (10)0.0213 (11)0.0032 (9)0.0009 (9)0.0071 (9)
C130.0258 (13)0.0221 (12)0.0339 (14)0.0051 (10)0.0025 (11)0.0166 (11)
C140.0324 (14)0.0258 (13)0.0252 (12)0.0102 (11)0.0016 (10)0.0159 (11)
C150.0163 (10)0.0170 (10)0.0141 (10)0.0053 (8)0.0009 (8)0.0060 (8)
C160.0177 (11)0.0180 (11)0.0140 (10)0.0086 (9)0.0005 (8)0.0056 (9)
C170.0188 (11)0.0150 (10)0.0162 (10)0.0063 (9)0.0030 (8)0.0049 (9)
C180.0174 (11)0.0178 (11)0.0169 (11)0.0031 (9)0.0024 (9)0.0019 (9)
C190.0204 (11)0.0275 (12)0.0148 (10)0.0126 (10)0.0013 (9)0.0059 (9)
C200.0205 (11)0.0238 (11)0.0164 (10)0.0119 (9)0.0045 (9)0.0101 (9)
Geometric parameters (Å, º) top
I1—C152.102 (2)C7—C81.399 (3)
F1—C171.354 (3)C8—C91.383 (3)
N1—C21.331 (3)C8—H80.9500
N1—C11.333 (3)C9—C101.410 (3)
C1—C41.392 (3)C9—H90.9500
C1—H10.9500C10—C111.406 (3)
I2—C162.100 (2)C11—C121.386 (3)
F2—C181.341 (3)C11—H110.9500
N2—C21.333 (3)C12—H120.9500
N2—C31.335 (3)C13—H13A0.9800
C2—H20.9500C13—H13B0.9800
F3—C191.342 (3)C13—H13C0.9800
N3—C101.381 (3)C14—H14A0.9800
N3—C131.456 (3)C14—H14B0.9800
N3—C141.457 (3)C14—H14C0.9800
C3—C41.392 (3)C15—C201.383 (3)
C3—H30.9500C15—C161.405 (3)
F4—C201.352 (3)C16—C171.381 (3)
C4—C51.431 (3)C17—C181.377 (3)
C5—C61.197 (3)C18—C191.382 (3)
C6—C71.432 (3)C19—C201.379 (3)
C7—C121.397 (3)
C2—N1—C1116.3 (2)C11—C12—C7121.0 (2)
N1—C1—C4122.8 (2)C11—C12—H12119.5
N1—C1—H1118.6C7—C12—H12119.5
C4—C1—H1118.6N3—C13—H13A109.5
C2—N2—C3116.3 (2)N3—C13—H13B109.5
N1—C2—N2126.4 (2)H13A—C13—H13B109.5
N1—C2—H2116.8N3—C13—H13C109.5
N2—C2—H2116.8H13A—C13—H13C109.5
C10—N3—C13119.2 (2)H13B—C13—H13C109.5
C10—N3—C14119.05 (19)N3—C14—H14A109.5
C13—N3—C14116.9 (2)N3—C14—H14B109.5
N2—C3—C4122.7 (2)H14A—C14—H14B109.5
N2—C3—H3118.7N3—C14—H14C109.5
C4—C3—H3118.7H14A—C14—H14C109.5
C1—C4—C3115.5 (2)H14B—C14—H14C109.5
C1—C4—C5122.1 (2)C20—C15—C16118.7 (2)
C3—C4—C5122.4 (2)C20—C15—I1118.66 (17)
C6—C5—C4179.0 (3)C16—C15—I1122.63 (16)
C5—C6—C7176.7 (2)C17—C16—C15118.5 (2)
C12—C7—C8118.2 (2)C17—C16—I2118.46 (16)
C12—C7—C6120.5 (2)C15—C16—I2122.97 (16)
C8—C7—C6121.2 (2)F1—C17—C18116.9 (2)
C9—C8—C7121.3 (2)F1—C17—C16120.9 (2)
C9—C8—H8119.4C18—C17—C16122.2 (2)
C7—C8—H8119.4F2—C18—C17120.4 (2)
C8—C9—C10120.8 (2)F2—C18—C19120.3 (2)
C8—C9—H9119.6C17—C18—C19119.2 (2)
C10—C9—H9119.6F3—C19—C20120.9 (2)
N3—C10—C11121.1 (2)F3—C19—C18119.9 (2)
N3—C10—C9121.2 (2)C20—C19—C18119.2 (2)
C11—C10—C9117.7 (2)F4—C20—C19117.1 (2)
C12—C11—C10121.1 (2)F4—C20—C15120.8 (2)
C12—C11—H11119.5C19—C20—C15122.0 (2)
C10—C11—H11119.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11···F2i0.952.633.220 (3)121
C14—H14B···F1ii0.982.613.541 (3)159
Symmetry codes: (i) x, y+2, z+1; (ii) x+1, y2, z.
5-{[4-(Dimethylamino)phenyl]ethynyl}pyrimidine–1,2,3,4-tetrafluoro-5,6-diiodobenzene–benzene (1/1/1) (6_eb951_a_F) top
Crystal data top
C14H13N3·C6F4I2·C6H6F(000) = 1352
Mr = 703.24Dx = 1.852 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 7.2512 (6) ÅCell parameters from 7881 reflections
b = 20.6215 (17) Åθ = 2.3–27.1°
c = 17.1906 (14) ŵ = 2.54 mm1
β = 101.166 (1)°T = 100 K
V = 2521.9 (4) Å3Cut block, colourless
Z = 40.40 × 0.25 × 0.04 mm
Data collection top
Bruker APEXII CCD
diffractometer
5618 independent reflections
Radiation source: fine-focus sealed tube4701 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
Detector resolution: 8.3660 pixels mm-1θmax = 27.2°, θmin = 2.0°
phi and ω scansh = 99
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
k = 2626
Tmin = 0.471, Tmax = 0.903l = 2222
28632 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.078 w = 1/[σ2(Fo2) + (0.0447P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
5618 reflectionsΔρmax = 1.93 e Å3
318 parametersΔρmin = 0.44 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
I10.74810 (3)0.58944 (2)0.35906 (2)0.02079 (7)
F10.8779 (3)0.53503 (10)0.67688 (11)0.0262 (5)
N10.7641 (4)0.65935 (14)0.21470 (16)0.0247 (7)
C10.9069 (5)0.64382 (18)0.1799 (2)0.0299 (9)
H10.9986080.6140180.2057250.036*
I20.93280 (3)0.64921 (2)0.56357 (2)0.02015 (7)
F20.7492 (3)0.41418 (9)0.65467 (11)0.0251 (5)
N20.6419 (4)0.72863 (14)0.10478 (16)0.0257 (7)
C20.9269 (5)0.66945 (19)0.1074 (2)0.0302 (8)
H21.0301790.6583730.0834280.036*
F30.6133 (3)0.36921 (9)0.50499 (12)0.0273 (5)
N30.2691 (4)0.83280 (15)0.35686 (16)0.0260 (7)
C30.7892 (5)0.71178 (18)0.0722 (2)0.0300 (8)
H30.7986240.7300060.0223410.036*
F40.6131 (3)0.44633 (9)0.37948 (11)0.0259 (4)
C40.6367 (5)0.70149 (16)0.17603 (19)0.0223 (7)
C50.4841 (5)0.71971 (17)0.21178 (19)0.0246 (8)
C60.3540 (5)0.73840 (16)0.2400 (2)0.0250 (8)
C70.1972 (5)0.76244 (16)0.27073 (19)0.0224 (7)
C80.0761 (5)0.80838 (17)0.2278 (2)0.0252 (8)
H80.1002440.8240000.1787080.030*
C90.0785 (5)0.83138 (17)0.25581 (19)0.0246 (8)
H90.1581710.8626870.2256980.030*
C100.1198 (5)0.80931 (16)0.32791 (19)0.0228 (7)
C110.0037 (5)0.76200 (16)0.36992 (19)0.0231 (7)
H110.0211320.7452480.4183410.028*
C120.1561 (5)0.74013 (16)0.34260 (19)0.0224 (7)
H120.2366210.7090940.3728000.027*
C130.3920 (6)0.8812 (2)0.3115 (2)0.0335 (9)
H13A0.3161640.9172470.2978780.050*
H13B0.4805820.8974040.3433560.050*
H13C0.4619350.8613910.2627790.050*
C140.3345 (5)0.79854 (19)0.4205 (2)0.0317 (9)
H14A0.3624320.7533800.4047880.047*
H14B0.4484830.8195040.4310220.047*
H14C0.2365540.7997030.4685960.047*
C150.7514 (5)0.53281 (16)0.46159 (18)0.0197 (7)
C160.8187 (4)0.55641 (16)0.53831 (19)0.0179 (7)
C170.8149 (5)0.51475 (17)0.60199 (18)0.0202 (7)
C180.7471 (5)0.45259 (16)0.59164 (19)0.0211 (7)
C190.6811 (5)0.42983 (16)0.5161 (2)0.0217 (7)
C200.6825 (5)0.47031 (17)0.45225 (19)0.0218 (7)
C210.6473 (7)0.5202 (3)0.8395 (3)0.0568 (13)
H210.6250200.5404630.7889530.068*
C220.7002 (7)0.5565 (2)0.9062 (3)0.0576 (13)
H220.7118530.6022170.9020120.069*
C230.7371 (8)0.5272 (3)0.9801 (3)0.0645 (15)
H230.7777020.5522591.0265590.077*
C240.7139 (7)0.4603 (2)0.9852 (3)0.0541 (13)
H240.7366330.4395281.0355220.065*
C250.6582 (6)0.4247 (2)0.9176 (3)0.0418 (11)
H250.6417690.3791480.9209350.050*
C260.6261 (6)0.4547 (2)0.8449 (3)0.0476 (12)
H260.5888190.4296500.7981290.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.02514 (13)0.02112 (13)0.01538 (11)0.00266 (9)0.00210 (9)0.00049 (8)
F10.0349 (12)0.0270 (11)0.0152 (9)0.0048 (9)0.0015 (8)0.0012 (8)
N10.0290 (17)0.0240 (16)0.0196 (14)0.0011 (13)0.0012 (12)0.0012 (12)
C10.033 (2)0.029 (2)0.0265 (19)0.0049 (16)0.0024 (16)0.0009 (15)
I20.02672 (13)0.01681 (12)0.01653 (11)0.00109 (8)0.00324 (9)0.00140 (8)
F20.0301 (12)0.0213 (11)0.0241 (10)0.0030 (8)0.0060 (9)0.0065 (8)
N20.0330 (18)0.0234 (16)0.0190 (14)0.0023 (13)0.0007 (13)0.0018 (12)
C20.032 (2)0.039 (2)0.0211 (18)0.0024 (17)0.0066 (15)0.0020 (16)
F30.0300 (11)0.0177 (10)0.0335 (11)0.0030 (8)0.0048 (9)0.0023 (8)
N30.0278 (17)0.0289 (17)0.0207 (15)0.0050 (13)0.0034 (13)0.0048 (12)
C30.039 (2)0.031 (2)0.0201 (17)0.0005 (17)0.0064 (16)0.0030 (15)
F40.0321 (12)0.0229 (11)0.0213 (10)0.0001 (9)0.0013 (8)0.0068 (8)
C40.0276 (19)0.0195 (18)0.0189 (16)0.0011 (14)0.0025 (14)0.0007 (13)
C50.033 (2)0.0197 (18)0.0197 (17)0.0009 (15)0.0026 (15)0.0031 (13)
C60.037 (2)0.0165 (17)0.0201 (17)0.0008 (15)0.0010 (15)0.0022 (13)
C70.028 (2)0.0168 (17)0.0213 (17)0.0026 (14)0.0037 (14)0.0008 (13)
C80.032 (2)0.0241 (19)0.0190 (17)0.0012 (15)0.0037 (15)0.0020 (14)
C90.034 (2)0.0204 (18)0.0191 (16)0.0054 (15)0.0045 (15)0.0043 (14)
C100.0286 (19)0.0209 (18)0.0172 (16)0.0003 (14)0.0004 (14)0.0012 (13)
C110.033 (2)0.0197 (18)0.0164 (15)0.0048 (15)0.0031 (14)0.0027 (13)
C120.030 (2)0.0163 (17)0.0187 (16)0.0004 (14)0.0012 (14)0.0020 (13)
C130.035 (2)0.036 (2)0.0281 (19)0.0105 (18)0.0032 (16)0.0036 (17)
C140.034 (2)0.038 (2)0.0261 (19)0.0025 (17)0.0117 (16)0.0038 (16)
C150.0195 (17)0.0238 (18)0.0155 (15)0.0015 (13)0.0028 (13)0.0014 (13)
C160.0160 (16)0.0180 (16)0.0198 (16)0.0027 (13)0.0037 (13)0.0004 (13)
C170.0205 (17)0.0256 (18)0.0137 (15)0.0033 (14)0.0014 (13)0.0010 (13)
C180.0190 (17)0.0240 (18)0.0210 (16)0.0028 (14)0.0060 (14)0.0053 (13)
C190.0214 (18)0.0165 (17)0.0285 (18)0.0009 (14)0.0081 (14)0.0009 (14)
C200.0221 (18)0.0238 (18)0.0181 (16)0.0031 (14)0.0008 (13)0.0051 (13)
C210.063 (3)0.049 (3)0.058 (3)0.007 (3)0.011 (3)0.018 (3)
C220.056 (3)0.034 (3)0.084 (4)0.000 (2)0.019 (3)0.002 (3)
C230.078 (4)0.048 (3)0.060 (3)0.004 (3)0.004 (3)0.021 (3)
C240.073 (4)0.047 (3)0.038 (3)0.004 (2)0.001 (2)0.001 (2)
C250.047 (3)0.034 (2)0.042 (2)0.0030 (19)0.001 (2)0.0020 (19)
C260.051 (3)0.049 (3)0.039 (2)0.001 (2)0.000 (2)0.003 (2)
Geometric parameters (Å, º) top
I1—C152.110 (3)C11—C121.359 (5)
F1—C171.347 (3)C11—H110.9500
N1—C11.331 (5)C12—H120.9500
N1—C41.347 (4)C13—H13A0.9800
C1—C21.387 (5)C13—H13B0.9800
C1—H10.9500C13—H13C0.9800
I2—C162.097 (3)C14—H14A0.9800
F2—C181.340 (4)C14—H14B0.9800
N2—C31.345 (5)C14—H14C0.9800
N2—C41.354 (4)C15—C201.380 (5)
C2—C31.376 (5)C15—C161.402 (4)
C2—H20.9500C16—C171.396 (4)
F3—C191.343 (4)C17—C181.372 (5)
N3—C101.365 (5)C18—C191.376 (5)
N3—C141.457 (4)C19—C201.381 (5)
N3—C131.459 (4)C21—C221.361 (7)
C3—H30.9500C21—C261.364 (7)
F4—C201.349 (4)C21—H210.9500
C4—C51.416 (5)C22—C231.386 (7)
C5—C61.205 (5)C22—H220.9500
C6—C71.432 (5)C23—C241.394 (7)
C7—C81.401 (5)C23—H230.9500
C7—C121.403 (5)C24—C251.368 (6)
C8—C91.387 (5)C24—H240.9500
C8—H80.9500C25—C261.372 (6)
C9—C101.406 (5)C25—H250.9500
C9—H90.9500C26—H260.9500
C10—C111.423 (5)
C1—N1—C4116.9 (3)N3—C14—H14A109.5
N1—C1—C2122.5 (3)N3—C14—H14B109.5
N1—C1—H1118.7H14A—C14—H14B109.5
C2—C1—H1118.7N3—C14—H14C109.5
C3—N2—C4115.7 (3)H14A—C14—H14C109.5
C3—C2—C1116.4 (4)H14B—C14—H14C109.5
C3—C2—H2121.8C20—C15—C16119.1 (3)
C1—C2—H2121.8C20—C15—I1118.3 (2)
C10—N3—C14119.9 (3)C16—C15—I1122.6 (2)
C10—N3—C13119.6 (3)C17—C16—C15117.9 (3)
C14—N3—C13118.6 (3)C17—C16—I2117.8 (2)
N2—C3—C2123.2 (3)C15—C16—I2124.3 (2)
N2—C3—H3118.4F1—C17—C18117.4 (3)
C2—C3—H3118.4F1—C17—C16120.3 (3)
N1—C4—N2125.2 (3)C18—C17—C16122.3 (3)
N1—C4—C5118.4 (3)F2—C18—C17120.0 (3)
N2—C4—C5116.3 (3)F2—C18—C19120.6 (3)
C6—C5—C4176.4 (4)C17—C18—C19119.4 (3)
C5—C6—C7177.6 (4)F3—C19—C18120.2 (3)
C8—C7—C12117.9 (3)F3—C19—C20120.5 (3)
C8—C7—C6120.0 (3)C18—C19—C20119.3 (3)
C12—C7—C6122.0 (3)F4—C20—C15120.8 (3)
C9—C8—C7120.9 (3)F4—C20—C19117.2 (3)
C9—C8—H8119.5C15—C20—C19122.0 (3)
C7—C8—H8119.5C22—C21—C26120.3 (5)
C8—C9—C10121.3 (3)C22—C21—H21119.8
C8—C9—H9119.3C26—C21—H21119.8
C10—C9—H9119.3C21—C22—C23120.3 (5)
N3—C10—C9121.7 (3)C21—C22—H22119.9
N3—C10—C11121.6 (3)C23—C22—H22119.9
C9—C10—C11116.7 (3)C22—C23—C24119.1 (5)
C12—C11—C10121.7 (3)C22—C23—H23120.4
C12—C11—H11119.1C24—C23—H23120.4
C10—C11—H11119.1C25—C24—C23119.7 (5)
C11—C12—C7121.4 (3)C25—C24—H24120.1
C11—C12—H12119.3C23—C24—H24120.1
C7—C12—H12119.3C24—C25—C26120.1 (4)
N3—C13—H13A109.5C24—C25—H25119.9
N3—C13—H13B109.5C26—C25—H25119.9
H13A—C13—H13B109.5C21—C26—C25120.4 (5)
N3—C13—H13C109.5C21—C26—H26119.8
H13A—C13—H13C109.5C25—C26—H26119.8
H13B—C13—H13C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9···F4i0.952.573.296 (4)134
C11—H11···I2ii0.953.254.173 (3)163
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x1, y, z.
2-{[4-(Dimethylamino)phenyl]ethynyl}pyrimidine–1,2,4,5-tetrafluoro-3,6-diiodobenzene (1/1) (7_eb945_a_tw) top
Crystal data top
C14H13N3·C6F4I2F(000) = 1184
Mr = 625.13Dx = 1.937 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.0191 (18) ÅCell parameters from 9994 reflections
b = 26.805 (5) Åθ = 2.4–27.3°
c = 9.5664 (19) ŵ = 2.98 mm1
β = 112.052 (3)°T = 100 K
V = 2143.6 (7) Å3Cut block, colourless
Z = 40.33 × 0.32 × 0.12 mm
Data collection top
Bruker APEXII CCD
diffractometer
4793 measured reflections
Radiation source: fine-focus sealed tube26551 independent reflections
Graphite monochromator4305 reflections with I > 2σ(I)
Detector resolution: 8.3660 pixels mm-1θmax = 27.4°, θmin = 1.5°
phi and ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
k = 3434
Tmin = 0.393, Tmax = 0.691l = 1012
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H-atom parameters constrained
wR(F2) = 0.147 w = 1/[σ2(Fo2) + 36.0237P]
where P = (Fo2 + 2Fc2)/3
S = 1.13(Δ/σ)max < 0.001
4793 reflectionsΔρmax = 3.63 e Å3
265 parametersΔρmin = 3.33 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.42385 (7)0.75016 (2)0.88434 (7)0.02056 (15)
F10.7099 (6)0.77369 (18)0.7652 (7)0.0251 (12)
N10.2630 (9)0.6585 (3)0.9476 (10)0.0226 (16)
C10.1539 (12)0.6603 (4)1.0098 (12)0.027 (2)
H10.1256890.6919561.0372590.032*
I20.69015 (7)0.97266 (2)0.67044 (7)0.02209 (15)
F20.8057 (7)0.8576 (2)0.6788 (7)0.0266 (13)
N20.2295 (10)0.5695 (3)0.9308 (10)0.0239 (16)
C20.0791 (12)0.6182 (4)1.0366 (12)0.031 (2)
H20.0021090.6204161.0821250.037*
F30.4304 (7)0.9485 (2)0.8144 (7)0.0305 (13)
N31.0120 (10)0.6228 (3)0.5699 (11)0.0278 (18)
C30.1217 (12)0.5730 (4)0.9941 (12)0.026 (2)
H30.0724270.5434521.0105000.031*
F40.3284 (7)0.8645 (2)0.8935 (7)0.0289 (13)
C40.2983 (11)0.6123 (3)0.9113 (11)0.0199 (18)
C50.4176 (11)0.6097 (3)0.8469 (10)0.0195 (18)
C60.5212 (11)0.6081 (3)0.7975 (11)0.0208 (19)
C70.6456 (10)0.6104 (3)0.7397 (10)0.0181 (17)
C80.7068 (11)0.5678 (3)0.6941 (11)0.0226 (19)
H80.6641730.5359380.7012650.027*
C90.8276 (11)0.5716 (3)0.6392 (12)0.0228 (19)
H90.8679200.5421070.6110600.027*
C100.8929 (11)0.6185 (3)0.6239 (11)0.0213 (19)
C110.8282 (11)0.6613 (3)0.6672 (11)0.0227 (19)
H110.8676590.6934230.6570460.027*
C120.7092 (11)0.6571 (3)0.7235 (11)0.0217 (19)
H120.6688180.6864180.7523650.026*
C131.0778 (12)0.5792 (4)0.5224 (12)0.026 (2)
H13A1.1191640.5557050.6066080.039*
H13B1.1648430.5896870.4911520.039*
H13C0.9936650.5630700.4375540.039*
C141.0742 (12)0.6715 (4)0.5514 (13)0.028 (2)
H14A0.9892440.6908340.4762500.042*
H14B1.1633180.6670680.5175380.042*
H14C1.1118650.6892040.6480410.042*
C150.5138 (11)0.8161 (3)0.8288 (11)0.0199 (18)
C160.6361 (11)0.8168 (3)0.7749 (10)0.0187 (18)
C170.6883 (10)0.8604 (3)0.7332 (10)0.0174 (17)
C180.6211 (11)0.9060 (3)0.7417 (11)0.0208 (18)
C190.5022 (12)0.9056 (3)0.8000 (11)0.024 (2)
C200.4484 (11)0.8620 (3)0.8413 (10)0.0205 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0219 (3)0.0166 (3)0.0240 (3)0.0029 (2)0.0095 (2)0.0011 (2)
F10.026 (3)0.012 (2)0.041 (3)0.002 (2)0.017 (3)0.001 (2)
N10.023 (4)0.020 (4)0.025 (4)0.000 (3)0.009 (3)0.004 (3)
C10.027 (5)0.027 (5)0.030 (5)0.005 (4)0.014 (4)0.004 (4)
I20.0227 (3)0.0142 (3)0.0275 (3)0.0015 (2)0.0074 (3)0.0033 (2)
F20.023 (3)0.022 (3)0.041 (4)0.001 (2)0.020 (3)0.001 (2)
N20.026 (4)0.021 (4)0.029 (4)0.001 (3)0.016 (4)0.000 (3)
C20.025 (5)0.044 (6)0.028 (6)0.001 (4)0.016 (5)0.003 (5)
F30.035 (3)0.016 (3)0.045 (4)0.006 (2)0.021 (3)0.001 (3)
N30.029 (4)0.018 (4)0.046 (5)0.005 (3)0.024 (4)0.001 (4)
C30.024 (5)0.020 (4)0.033 (5)0.004 (4)0.010 (4)0.005 (4)
F40.032 (3)0.023 (3)0.040 (3)0.003 (2)0.022 (3)0.000 (3)
C40.022 (4)0.015 (4)0.026 (5)0.001 (3)0.013 (4)0.001 (4)
C50.019 (4)0.017 (4)0.021 (4)0.001 (3)0.006 (4)0.001 (3)
C60.021 (4)0.014 (4)0.025 (5)0.001 (3)0.006 (4)0.000 (3)
C70.013 (4)0.024 (4)0.017 (4)0.002 (3)0.005 (3)0.003 (4)
C80.019 (4)0.022 (4)0.026 (5)0.003 (3)0.009 (4)0.002 (4)
C90.025 (5)0.016 (4)0.034 (5)0.004 (3)0.019 (4)0.002 (4)
C100.020 (4)0.019 (4)0.025 (5)0.001 (3)0.009 (4)0.004 (4)
C110.023 (4)0.015 (4)0.031 (5)0.001 (3)0.010 (4)0.004 (4)
C120.018 (4)0.020 (4)0.027 (5)0.004 (3)0.009 (4)0.003 (4)
C130.023 (5)0.027 (5)0.029 (5)0.001 (4)0.011 (4)0.003 (4)
C140.027 (5)0.021 (5)0.044 (6)0.003 (4)0.022 (5)0.004 (4)
C150.026 (4)0.014 (4)0.020 (4)0.003 (3)0.009 (4)0.001 (3)
C160.019 (4)0.009 (4)0.024 (5)0.001 (3)0.004 (4)0.003 (3)
C170.019 (4)0.016 (4)0.018 (4)0.002 (3)0.008 (4)0.000 (3)
C180.023 (4)0.015 (4)0.022 (5)0.003 (3)0.006 (4)0.001 (3)
C190.029 (5)0.017 (4)0.022 (5)0.002 (4)0.006 (4)0.003 (4)
C200.020 (4)0.022 (4)0.023 (4)0.000 (4)0.012 (4)0.001 (4)
Geometric parameters (Å, º) top
I1—C152.096 (9)C7—C121.410 (12)
F1—C161.355 (10)C8—C91.379 (13)
N1—C11.329 (13)C8—H80.9500
N1—C41.357 (11)C9—C101.419 (12)
C1—C21.387 (15)C9—H90.9500
C1—H10.9500C10—C111.419 (13)
I2—C182.090 (9)C11—C121.374 (13)
F2—C171.346 (10)C11—H110.9500
N2—C31.328 (13)C12—H120.9500
N2—C41.348 (11)C13—H13A0.9800
C2—C31.377 (14)C13—H13B0.9800
C2—H20.9500C13—H13C0.9800
F3—C191.353 (10)C14—H14A0.9800
N3—C101.360 (12)C14—H14B0.9800
N3—C131.456 (12)C14—H14C0.9800
N3—C141.458 (12)C15—C161.382 (13)
C3—H30.9500C15—C201.386 (12)
F4—C201.353 (10)C16—C171.375 (12)
C4—C51.428 (13)C17—C181.378 (12)
C5—C61.196 (13)C18—C191.382 (14)
C6—C71.427 (13)C19—C201.379 (13)
C7—C81.406 (13)
C1—N1—C4115.6 (8)C11—C12—C7121.8 (9)
N1—C1—C2123.1 (9)C11—C12—H12119.1
N1—C1—H1118.5C7—C12—H12119.1
C2—C1—H1118.5N3—C13—H13A109.5
C3—N2—C4117.2 (8)N3—C13—H13B109.5
C3—C2—C1116.9 (9)H13A—C13—H13B109.5
C3—C2—H2121.6N3—C13—H13C109.5
C1—C2—H2121.6H13A—C13—H13C109.5
C10—N3—C13121.5 (8)H13B—C13—H13C109.5
C10—N3—C14121.1 (8)N3—C14—H14A109.5
C13—N3—C14117.3 (8)N3—C14—H14B109.5
N2—C3—C2122.0 (9)H14A—C14—H14B109.5
N2—C3—H3119.0N3—C14—H14C109.5
C2—C3—H3119.0H14A—C14—H14C109.5
N2—C4—N1125.2 (8)H14B—C14—H14C109.5
N2—C4—C5118.6 (8)C16—C15—C20116.4 (8)
N1—C4—C5116.2 (8)C16—C15—I1123.0 (6)
C6—C5—C4177.8 (10)C20—C15—I1120.5 (7)
C5—C6—C7175.4 (10)F1—C16—C17118.3 (8)
C8—C7—C12117.6 (8)F1—C16—C15119.8 (8)
C8—C7—C6122.8 (8)C17—C16—C15121.9 (8)
C12—C7—C6119.5 (8)F2—C17—C16118.0 (8)
C9—C8—C7121.1 (9)F2—C17—C18120.0 (8)
C9—C8—H8119.4C16—C17—C18122.0 (8)
C7—C8—H8119.4C17—C18—C19116.3 (8)
C8—C9—C10121.5 (9)C17—C18—I2123.1 (7)
C8—C9—H9119.3C19—C18—I2120.6 (7)
C10—C9—H9119.3F3—C19—C20117.3 (9)
N3—C10—C11120.8 (8)F3—C19—C18120.5 (8)
N3—C10—C9122.1 (9)C20—C19—C18122.1 (9)
C11—C10—C9117.0 (8)F4—C20—C19118.6 (8)
C12—C11—C10121.0 (8)F4—C20—C15120.1 (8)
C12—C11—H11119.5C19—C20—C15121.3 (8)
C10—C11—H11119.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···F2i0.952.363.297 (12)169
C13—H13A···I2ii0.983.124.069 (10)165
C13—H13B···F4iii0.982.363.316 (12)164
C13—H13C···I2iv0.983.114.081 (10)170
C14—H14B···F4iii0.982.383.327 (12)162
C14—H14C···I1v0.983.304.123 (11)142
Symmetry codes: (i) x1, y+3/2, z+1/2; (ii) x+2, y1/2, z+3/2; (iii) x+1, y+3/2, z1/2; (iv) x, y+3/2, z1/2; (v) x+1, y, z.
 

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