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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
CCDC references: 1996176; 1996175; 1996174; 1996173; 1996172; 1996171; 1996170
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·C6F4I2 | F(000) = 2176 |
Mr = 584.05 | Dx = 2.282 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 27.2812 (12) Å | Cell parameters from 9912 reflections |
b = 6.2100 (3) Å | θ = 2.9–27.2° |
c = 20.9742 (9) Å | µ = 3.75 mm−1 |
β = 106.931 (1)° | T = 100 K |
V = 3399.4 (3) Å3 | Cut, colourless |
Z = 8 | 0.2 × 0.1 × 0.03 mm |
Data collection top
Bruker APEXII CCD diffractometer | 3766 independent reflections |
Radiation source: fine-focus sealed tube | 3544 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
Detector resolution: 8.3660 pixels mm-1 | θmax = 27.2°, θmin = 2.0° |
phi and ω scans | h = −34→34 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −7→7 |
Tmin = 0.644, Tmax = 0.894 | l = −26→26 |
19984 measured reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.020 | H-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 reflections | Δρmax = 1.22 e Å−3 |
235 parameters | Δρmin = −0.46 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 | 0.71386 (2) | 0.64479 (2) | 0.38942 (2) | 0.01647 (5) | |
F1 | 0.77768 (5) | 0.7557 (2) | 0.28731 (7) | 0.0187 (3) | |
N1 | 0.64733 (8) | 0.8906 (3) | 0.44851 (10) | 0.0166 (4) | |
C1 | 0.61871 (9) | 0.7914 (4) | 0.48177 (12) | 0.0176 (5) | |
H1 | 0.618534 | 0.638559 | 0.483244 | 0.021* | |
I2 | 0.87690 (2) | 0.61878 (2) | 0.24466 (2) | 0.01686 (5) | |
F2 | 0.88729 (5) | 0.1537 (2) | 0.31325 (7) | 0.0221 (3) | |
N2 | 0.61952 (7) | 1.2324 (3) | 0.47719 (10) | 0.0187 (4) | |
C2 | 0.64661 (9) | 1.1054 (4) | 0.44840 (12) | 0.0173 (5) | |
H2 | 0.667471 | 1.175490 | 0.425536 | 0.021* | |
F3 | 0.83918 (5) | −0.0311 (2) | 0.39399 (7) | 0.0224 (3) | |
N3 | 0.44514 (8) | 0.6426 (3) | 0.68510 (11) | 0.0188 (4) | |
C3 | 0.59090 (9) | 1.1307 (4) | 0.50990 (12) | 0.0173 (5) | |
H3 | 0.570966 | 1.214648 | 0.530956 | 0.021* | |
F4 | 0.76310 (5) | 0.1776 (2) | 0.42656 (7) | 0.0208 (3) | |
N4 | 0.46927 (8) | 0.2967 (3) | 0.65483 (11) | 0.0213 (4) | |
C4 | 0.58901 (9) | 0.9068 (4) | 0.51447 (12) | 0.0151 (4) | |
C5 | 0.55827 (9) | 0.8022 (4) | 0.55049 (12) | 0.0194 (5) | |
C6 | 0.53333 (9) | 0.7184 (4) | 0.58159 (12) | 0.0189 (5) | |
C7 | 0.50276 (9) | 0.6167 (4) | 0.61884 (12) | 0.0168 (5) | |
C8 | 0.47516 (9) | 0.7373 (4) | 0.65275 (12) | 0.0193 (5) | |
H8 | 0.477670 | 0.889926 | 0.652936 | 0.023* | |
C9 | 0.44393 (9) | 0.4276 (4) | 0.68436 (12) | 0.0198 (5) | |
H9 | 0.422707 | 0.360904 | 0.707386 | 0.024* | |
C10 | 0.49836 (9) | 0.3937 (4) | 0.62182 (13) | 0.0193 (5) | |
H10 | 0.516800 | 0.306653 | 0.599460 | 0.023* | |
C11 | 0.76858 (8) | 0.4738 (4) | 0.35771 (11) | 0.0149 (4) | |
C12 | 0.79342 (8) | 0.5618 (4) | 0.31458 (11) | 0.0146 (5) | |
C13 | 0.83388 (8) | 0.4621 (4) | 0.29861 (11) | 0.0150 (4) | |
C14 | 0.84753 (8) | 0.2595 (4) | 0.32529 (11) | 0.0159 (5) | |
C15 | 0.82325 (9) | 0.1620 (4) | 0.36694 (12) | 0.0161 (5) | |
C16 | 0.78434 (8) | 0.2708 (4) | 0.38301 (11) | 0.0156 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.01574 (8) | 0.01570 (9) | 0.02075 (9) | 0.00149 (5) | 0.00968 (6) | −0.00026 (6) |
F1 | 0.0219 (7) | 0.0146 (7) | 0.0206 (7) | 0.0040 (5) | 0.0080 (6) | 0.0050 (5) |
N1 | 0.0166 (10) | 0.0194 (10) | 0.0163 (10) | 0.0017 (8) | 0.0086 (8) | 0.0006 (8) |
C1 | 0.0203 (12) | 0.0175 (11) | 0.0162 (12) | 0.0010 (9) | 0.0074 (9) | 0.0006 (9) |
I2 | 0.01862 (9) | 0.01897 (9) | 0.01590 (9) | −0.00233 (5) | 0.00958 (6) | −0.00125 (5) |
F2 | 0.0202 (7) | 0.0221 (7) | 0.0271 (8) | 0.0071 (6) | 0.0119 (6) | −0.0008 (6) |
N2 | 0.0211 (10) | 0.0166 (10) | 0.0201 (10) | 0.0003 (8) | 0.0084 (8) | −0.0001 (8) |
C2 | 0.0172 (11) | 0.0199 (12) | 0.0168 (12) | −0.0014 (9) | 0.0079 (9) | 0.0005 (9) |
F3 | 0.0266 (7) | 0.0145 (7) | 0.0258 (8) | 0.0047 (6) | 0.0071 (6) | 0.0043 (6) |
N3 | 0.0190 (10) | 0.0221 (11) | 0.0186 (11) | 0.0002 (8) | 0.0107 (8) | −0.0003 (8) |
C3 | 0.0165 (11) | 0.0204 (12) | 0.0167 (12) | 0.0021 (9) | 0.0077 (9) | −0.0019 (9) |
F4 | 0.0242 (7) | 0.0189 (7) | 0.0231 (8) | −0.0011 (6) | 0.0129 (6) | 0.0055 (6) |
N4 | 0.0205 (10) | 0.0201 (10) | 0.0249 (11) | −0.0010 (8) | 0.0091 (9) | −0.0015 (9) |
C4 | 0.0116 (10) | 0.0212 (11) | 0.0130 (11) | −0.0007 (9) | 0.0040 (9) | 0.0012 (9) |
C5 | 0.0176 (11) | 0.0226 (12) | 0.0193 (12) | 0.0020 (9) | 0.0073 (10) | 0.0013 (10) |
C6 | 0.0171 (11) | 0.0220 (12) | 0.0178 (12) | 0.0016 (9) | 0.0055 (9) | −0.0004 (10) |
C7 | 0.0154 (11) | 0.0224 (12) | 0.0134 (11) | −0.0008 (9) | 0.0057 (9) | 0.0008 (9) |
C8 | 0.0203 (12) | 0.0192 (12) | 0.0203 (12) | 0.0010 (9) | 0.0088 (10) | 0.0015 (10) |
C9 | 0.0178 (11) | 0.0247 (12) | 0.0204 (12) | −0.0020 (10) | 0.0110 (10) | 0.0015 (10) |
C10 | 0.0163 (11) | 0.0231 (12) | 0.0200 (13) | 0.0004 (9) | 0.0075 (10) | −0.0024 (10) |
C11 | 0.0140 (10) | 0.0149 (11) | 0.0171 (11) | −0.0004 (8) | 0.0064 (9) | −0.0015 (9) |
C12 | 0.0176 (11) | 0.0111 (11) | 0.0157 (12) | 0.0000 (8) | 0.0057 (9) | −0.0001 (8) |
C13 | 0.0144 (10) | 0.0187 (11) | 0.0130 (11) | −0.0010 (9) | 0.0058 (9) | −0.0012 (9) |
C14 | 0.0126 (10) | 0.0185 (11) | 0.0170 (11) | 0.0020 (9) | 0.0050 (9) | −0.0035 (9) |
C15 | 0.0176 (11) | 0.0124 (10) | 0.0163 (12) | 0.0023 (8) | 0.0019 (9) | 0.0001 (8) |
C16 | 0.0167 (11) | 0.0165 (11) | 0.0148 (11) | −0.0033 (9) | 0.0066 (9) | 0.0004 (9) |
Geometric parameters (Å, º) top
I1—C11 | 2.092 (2) | N4—C9 | 1.331 (3) |
F1—C12 | 1.348 (3) | N4—C10 | 1.339 (3) |
N1—C2 | 1.334 (3) | C4—C5 | 1.437 (3) |
N1—C1 | 1.339 (3) | C5—C6 | 1.191 (4) |
C1—C4 | 1.401 (3) | C6—C7 | 1.444 (3) |
C1—H1 | 0.9500 | C7—C10 | 1.393 (3) |
I2—C13 | 2.092 (2) | C7—C8 | 1.395 (3) |
F2—C14 | 1.353 (2) | C8—H8 | 0.9500 |
N2—C3 | 1.339 (3) | C9—H9 | 0.9500 |
N2—C2 | 1.339 (3) | C10—H10 | 0.9500 |
C2—H2 | 0.9500 | C11—C16 | 1.387 (3) |
F3—C15 | 1.343 (3) | C11—C12 | 1.390 (3) |
N3—C9 | 1.336 (3) | C12—C13 | 1.389 (3) |
N3—C8 | 1.342 (3) | C13—C14 | 1.383 (3) |
C3—C4 | 1.396 (3) | C14—C15 | 1.381 (3) |
C3—H3 | 0.9500 | C15—C16 | 1.380 (3) |
F4—C16 | 1.347 (3) | | |
| | | |
C2—N1—C1 | 116.7 (2) | N4—C9—N3 | 127.0 (2) |
N1—C1—C4 | 121.9 (2) | N4—C9—H9 | 116.5 |
N1—C1—H1 | 119.1 | N3—C9—H9 | 116.5 |
C4—C1—H1 | 119.1 | N4—C10—C7 | 122.8 (2) |
C3—N2—C2 | 115.7 (2) | N4—C10—H10 | 118.6 |
N1—C2—N2 | 126.7 (2) | C7—C10—H10 | 118.6 |
N1—C2—H2 | 116.6 | C16—C11—C12 | 116.8 (2) |
N2—C2—H2 | 116.6 | C16—C11—I1 | 120.67 (16) |
C9—N3—C8 | 116.7 (2) | C12—C11—I1 | 122.37 (17) |
N2—C3—C4 | 123.0 (2) | F1—C12—C13 | 118.23 (19) |
N2—C3—H3 | 118.5 | F1—C12—C11 | 118.15 (19) |
C4—C3—H3 | 118.5 | C13—C12—C11 | 123.6 (2) |
C9—N4—C10 | 115.6 (2) | C14—C13—C12 | 116.6 (2) |
C3—C4—C1 | 115.9 (2) | C14—C13—I2 | 120.95 (16) |
C3—C4—C5 | 121.7 (2) | C12—C13—I2 | 122.24 (17) |
C1—C4—C5 | 122.4 (2) | F2—C14—C15 | 117.6 (2) |
C6—C5—C4 | 178.5 (3) | F2—C14—C13 | 120.1 (2) |
C5—C6—C7 | 179.6 (3) | C15—C14—C13 | 122.2 (2) |
C10—C7—C8 | 116.4 (2) | F3—C15—C16 | 120.7 (2) |
C10—C7—C6 | 122.0 (2) | F3—C15—C14 | 120.2 (2) |
C8—C7—C6 | 121.6 (2) | C16—C15—C14 | 119.0 (2) |
N3—C8—C7 | 121.4 (2) | F4—C16—C15 | 117.9 (2) |
N3—C8—H8 | 119.3 | F4—C16—C11 | 120.24 (19) |
C7—C8—H8 | 119.3 | C15—C16—C11 | 121.8 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···N2i | 0.95 | 2.53 | 3.473 (3) | 175 |
C2—H2···F4ii | 0.95 | 2.60 | 3.370 (3) | 138 |
C8—H8···N4ii | 0.95 | 2.54 | 3.478 (3) | 171 |
Symmetry codes: (i) x, y−1, 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·C6F4I2 | F(000) = 1040 |
Mr = 560.03 | Dx = 2.330 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.4617 (10) Å | Cell parameters from 6501 reflections |
b = 6.4681 (6) Å | θ = 2.8–27.1° |
c = 23.966 (2) Å | µ = 3.99 mm−1 |
β = 100.069 (1)° | T = 100 K |
V = 1596.7 (3) Å3 | Cut, colourless |
Z = 4 | 0.44 × 0.23 × 0.09 mm |
Data collection top
Bruker APEXII CCD diffractometer | 3557 independent reflections |
Radiation source: fine-focus sealed tube | 3283 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
Detector resolution: 8.3660 pixels mm-1 | θmax = 27.2°, θmin = 1.7° |
phi and ω scans | h = −13→13 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −8→8 |
Tmin = 0.345, Tmax = 0.699 | l = −30→30 |
18558 measured reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.029 | H-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 reflections | Δρmax = 0.94 e Å−3 |
217 parameters | Δρmin = −1.00 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 | 0.37336 (2) | 0.38726 (4) | 0.71890 (2) | 0.01442 (6) | |
F1 | 0.5983 (2) | 0.2430 (3) | 0.65150 (9) | 0.0174 (5) | |
N1 | 0.2137 (3) | 0.2038 (5) | 0.79103 (13) | 0.0166 (7) | |
C1 | 0.1543 (4) | 0.3107 (6) | 0.82688 (15) | 0.0161 (8) | |
H1 | 0.187715 | 0.442645 | 0.839314 | 0.019* | |
I2 | 0.73110 (2) | 0.35214 (4) | 0.54356 (2) | 0.01583 (7) | |
F2 | 0.6115 (2) | 0.8049 (3) | 0.52729 (9) | 0.0216 (5) | |
N2 | 0.0607 (3) | −0.0699 (5) | 0.79163 (13) | 0.0193 (7) | |
C2 | 0.1635 (4) | 0.0179 (6) | 0.77553 (16) | 0.0179 (8) | |
H2 | 0.205655 | −0.059575 | 0.750368 | 0.022* | |
F3 | 0.4345 (2) | 1.0065 (3) | 0.57584 (9) | 0.0204 (5) | |
N3 | −0.1352 (3) | 0.3714 (5) | 0.96376 (13) | 0.0179 (7) | |
C3 | 0.0023 (4) | 0.0433 (6) | 0.82699 (16) | 0.0169 (8) | |
H3 | −0.072545 | −0.011548 | 0.839122 | 0.020* | |
F4 | 0.3330 (2) | 0.8283 (3) | 0.65982 (9) | 0.0197 (5) | |
N4 | −0.0976 (3) | 0.6816 (5) | 0.91511 (14) | 0.0194 (7) | |
C4 | 0.0467 (4) | 0.2373 (6) | 0.84653 (15) | 0.0142 (7) | |
C5 | −0.0210 (4) | 0.3555 (6) | 0.88593 (15) | 0.0149 (7) | |
C6 | −0.0729 (4) | 0.2630 (6) | 0.92913 (15) | 0.0160 (8) | |
H6 | −0.064019 | 0.117798 | 0.934357 | 0.019* | |
C7 | −0.1446 (4) | 0.5748 (6) | 0.95445 (17) | 0.0188 (8) | |
H7 | −0.189814 | 0.651775 | 0.978591 | 0.023* | |
C8 | −0.0361 (4) | 0.5689 (6) | 0.88104 (16) | 0.0169 (8) | |
H8 | −0.001193 | 0.638065 | 0.852116 | 0.020* | |
C9 | 0.4617 (3) | 0.5277 (5) | 0.65676 (14) | 0.0123 (7) | |
C10 | 0.5548 (4) | 0.4301 (5) | 0.63152 (15) | 0.0138 (7) | |
C11 | 0.6071 (3) | 0.5156 (6) | 0.58747 (15) | 0.0131 (7) | |
C12 | 0.5653 (4) | 0.7124 (6) | 0.57009 (14) | 0.0137 (7) | |
C13 | 0.4751 (4) | 0.8188 (5) | 0.59472 (15) | 0.0138 (7) | |
C14 | 0.4237 (4) | 0.7253 (6) | 0.63740 (15) | 0.0137 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.01711 (13) | 0.01538 (11) | 0.01217 (11) | −0.00043 (9) | 0.00645 (9) | 0.00128 (9) |
F1 | 0.0226 (12) | 0.0133 (10) | 0.0180 (11) | 0.0042 (9) | 0.0086 (9) | 0.0033 (8) |
N1 | 0.0183 (17) | 0.0186 (16) | 0.0136 (16) | 0.0012 (13) | 0.0049 (13) | 0.0032 (13) |
C1 | 0.018 (2) | 0.0159 (18) | 0.0144 (18) | −0.0007 (15) | 0.0027 (15) | 0.0036 (14) |
I2 | 0.01594 (13) | 0.01947 (12) | 0.01335 (12) | 0.00000 (10) | 0.00608 (9) | −0.00225 (9) |
F2 | 0.0245 (13) | 0.0252 (12) | 0.0176 (11) | −0.0005 (10) | 0.0108 (10) | 0.0092 (9) |
N2 | 0.0245 (19) | 0.0178 (16) | 0.0171 (16) | −0.0008 (14) | 0.0079 (14) | −0.0019 (13) |
C2 | 0.020 (2) | 0.0200 (19) | 0.0137 (18) | 0.0027 (16) | 0.0029 (16) | 0.0023 (15) |
F3 | 0.0257 (13) | 0.0146 (11) | 0.0200 (12) | 0.0031 (9) | 0.0018 (10) | 0.0065 (9) |
N3 | 0.0175 (17) | 0.0220 (17) | 0.0159 (16) | −0.0015 (14) | 0.0080 (13) | 0.0027 (13) |
C3 | 0.017 (2) | 0.0164 (18) | 0.0182 (19) | −0.0008 (15) | 0.0048 (16) | 0.0028 (15) |
F4 | 0.0222 (12) | 0.0200 (11) | 0.0184 (11) | 0.0064 (9) | 0.0080 (9) | 0.0011 (9) |
N4 | 0.0208 (18) | 0.0177 (16) | 0.0213 (17) | −0.0019 (13) | 0.0080 (14) | −0.0009 (13) |
C4 | 0.0156 (19) | 0.0165 (18) | 0.0110 (17) | 0.0013 (15) | 0.0035 (15) | 0.0020 (14) |
C5 | 0.0136 (18) | 0.0161 (18) | 0.0151 (17) | −0.0001 (15) | 0.0024 (14) | 0.0005 (15) |
C6 | 0.018 (2) | 0.0158 (18) | 0.0148 (18) | −0.0011 (15) | 0.0050 (16) | 0.0033 (14) |
C7 | 0.017 (2) | 0.0193 (19) | 0.021 (2) | −0.0026 (15) | 0.0070 (16) | −0.0028 (15) |
C8 | 0.019 (2) | 0.0171 (18) | 0.0159 (19) | −0.0024 (15) | 0.0080 (16) | 0.0015 (14) |
C9 | 0.0128 (18) | 0.0156 (17) | 0.0091 (17) | −0.0005 (14) | 0.0032 (14) | 0.0002 (13) |
C10 | 0.0167 (19) | 0.0117 (17) | 0.0127 (17) | −0.0007 (14) | 0.0021 (14) | −0.0002 (14) |
C11 | 0.0109 (18) | 0.0197 (18) | 0.0090 (17) | −0.0014 (14) | 0.0031 (14) | −0.0014 (14) |
C12 | 0.0150 (19) | 0.0193 (18) | 0.0065 (16) | −0.0044 (15) | 0.0009 (14) | 0.0030 (13) |
C13 | 0.0158 (19) | 0.0130 (17) | 0.0115 (17) | −0.0004 (14) | −0.0008 (15) | 0.0005 (13) |
C14 | 0.0141 (19) | 0.0163 (18) | 0.0109 (17) | 0.0013 (14) | 0.0026 (14) | −0.0035 (14) |
Geometric parameters (Å, º) top
I1—C9 | 2.092 (3) | F4—C14 | 1.346 (4) |
F1—C10 | 1.351 (4) | N4—C7 | 1.331 (5) |
N1—C1 | 1.337 (5) | N4—C8 | 1.340 (5) |
N1—C2 | 1.338 (5) | C4—C5 | 1.487 (5) |
C1—C4 | 1.379 (5) | C5—C6 | 1.386 (5) |
C1—H1 | 0.9500 | C5—C8 | 1.392 (5) |
I2—C11 | 2.094 (4) | C6—H6 | 0.9500 |
F2—C12 | 1.348 (4) | C7—H7 | 0.9500 |
N2—C2 | 1.332 (5) | C8—H8 | 0.9500 |
N2—C3 | 1.345 (5) | C9—C10 | 1.386 (5) |
C2—H2 | 0.9500 | C9—C14 | 1.394 (5) |
F3—C13 | 1.339 (4) | C10—C11 | 1.386 (5) |
N3—C7 | 1.335 (5) | C11—C12 | 1.386 (5) |
N3—C6 | 1.339 (5) | C12—C13 | 1.381 (5) |
C3—C4 | 1.390 (5) | C13—C14 | 1.376 (5) |
C3—H3 | 0.9500 | | |
| | | |
C1—N1—C2 | 116.0 (3) | N4—C7—H7 | 116.4 |
N1—C1—C4 | 122.7 (4) | N3—C7—H7 | 116.4 |
N1—C1—H1 | 118.7 | N4—C8—C5 | 123.2 (3) |
C4—C1—H1 | 118.7 | N4—C8—H8 | 118.4 |
C2—N2—C3 | 115.4 (3) | C5—C8—H8 | 118.4 |
N2—C2—N1 | 126.9 (4) | C10—C9—C14 | 117.0 (3) |
N2—C2—H2 | 116.5 | C10—C9—I1 | 123.0 (3) |
N1—C2—H2 | 116.5 | C14—C9—I1 | 120.0 (3) |
C7—N3—C6 | 116.2 (3) | F1—C10—C9 | 118.2 (3) |
N2—C3—C4 | 122.8 (4) | F1—C10—C11 | 118.3 (3) |
N2—C3—H3 | 118.6 | C9—C10—C11 | 123.5 (3) |
C4—C3—H3 | 118.6 | C10—C11—C12 | 116.7 (3) |
C7—N4—C8 | 115.2 (3) | C10—C11—I2 | 122.9 (3) |
C1—C4—C3 | 116.1 (3) | C12—C11—I2 | 120.2 (3) |
C1—C4—C5 | 123.2 (3) | F2—C12—C13 | 117.8 (3) |
C3—C4—C5 | 120.7 (3) | F2—C12—C11 | 120.0 (3) |
C6—C5—C8 | 115.9 (3) | C13—C12—C11 | 122.2 (3) |
C6—C5—C4 | 123.0 (3) | F3—C13—C14 | 120.5 (3) |
C8—C5—C4 | 121.1 (3) | F3—C13—C12 | 120.5 (3) |
N3—C6—C5 | 122.3 (3) | C14—C13—C12 | 118.9 (3) |
N3—C6—H6 | 118.9 | F4—C14—C13 | 118.3 (3) |
C5—C6—H6 | 118.9 | F4—C14—C9 | 120.1 (3) |
N4—C7—N3 | 127.2 (4) | C13—C14—C9 | 121.7 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···I1i | 0.95 | 3.28 | 4.020 (4) | 137 |
C7—H7···F2ii | 0.95 | 2.57 | 3.424 (4) | 150 |
C8—H8···N2iii | 0.95 | 2.53 | 3.440 (5) | 160 |
Symmetry codes: (i) −x, y−1/2, −z+3/2; (ii) x−1, −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·C6F4I2 | F(000) = 592 |
Mr = 625.13 | Dx = 1.943 Mg m−3 |
Monoclinic, P21/m | Mo Kα radiation, λ = 0.71073 Å |
a = 6.9939 (5) Å | Cell parameters from 9430 reflections |
b = 13.640 (1) Å | θ = 2.4–27.1° |
c = 11.2299 (8) Å | µ = 2.99 mm−1 |
β = 94.260 (1)° | T = 100 K |
V = 1068.34 (13) Å3 | Cut BLOCK, colourless |
Z = 2 | 0.25 × 0.20 × 0.10 mm |
Data collection top
Bruker APEXII CCD diffractometer | 2445 independent reflections |
Radiation source: fine-focus sealed tube | 2326 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.015 |
Detector resolution: 8.3660 pixels mm-1 | θmax = 27.1°, θmin = 1.8° |
phi and ω scans | h = −8→8 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −17→17 |
Tmin = 0.493, Tmax = 0.742 | l = −14→14 |
13568 measured reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.018 | H-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 reflections | Δρmax = 1.12 e Å−3 |
149 parameters | Δρmin = −0.56 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 | 0.17202 (2) | 0.52669 (2) | 0.69662 (2) | 0.02063 (5) | |
F1 | 0.2034 (2) | 0.750000 | 0.61207 (14) | 0.0201 (3) | |
N1 | 0.2135 (2) | 0.33712 (12) | 0.58048 (15) | 0.0211 (3) | |
C1 | 0.1924 (4) | 0.250000 | 0.6314 (2) | 0.0208 (5) | |
H1 | 0.158963 | 0.250000 | 0.711835 | 0.025* | |
F2 | 0.06563 (19) | 0.57924 (9) | 0.96021 (11) | 0.0286 (3) | |
N2 | 0.6266 (4) | 0.250000 | −0.2843 (2) | 0.0227 (5) | |
C2 | 0.2628 (3) | 0.33650 (15) | 0.46776 (18) | 0.0217 (4) | |
H2 | 0.280177 | 0.397342 | 0.428837 | 0.026* | |
F3 | 0.0162 (3) | 0.750000 | 1.07364 (15) | 0.0267 (4) | |
C3 | 0.2895 (4) | 0.250000 | 0.4052 (2) | 0.0192 (5) | |
C4 | 0.3387 (4) | 0.250000 | 0.2838 (3) | 0.0245 (6) | |
C5 | 0.3753 (4) | 0.250000 | 0.1819 (3) | 0.0246 (6) | |
C6 | 0.4261 (4) | 0.250000 | 0.0604 (3) | 0.0226 (6) | |
C7 | 0.4557 (3) | 0.33794 (16) | 0.00044 (18) | 0.0244 (4) | |
H7 | 0.431226 | 0.398429 | 0.038398 | 0.029* | |
C8 | 0.5200 (3) | 0.33845 (16) | −0.11335 (18) | 0.0234 (4) | |
H8 | 0.538834 | 0.399188 | −0.152202 | 0.028* | |
C9 | 0.5579 (4) | 0.250000 | −0.1722 (2) | 0.0204 (5) | |
C10 | 0.7009 (3) | 0.34144 (17) | −0.32998 (19) | 0.0275 (5) | |
H10A | 0.598252 | 0.390477 | −0.336868 | 0.041* | |
H10B | 0.748342 | 0.329923 | −0.408722 | 0.041* | |
H10C | 0.805990 | 0.365351 | −0.275003 | 0.041* | |
C11 | 0.1585 (4) | 0.750000 | 0.7276 (2) | 0.0157 (5) | |
C12 | 0.1363 (3) | 0.66066 (13) | 0.78312 (17) | 0.0165 (4) | |
C13 | 0.0885 (3) | 0.66292 (14) | 0.90066 (17) | 0.0184 (4) | |
C14 | 0.0633 (4) | 0.750000 | 0.9597 (2) | 0.0187 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.02501 (8) | 0.01135 (7) | 0.02520 (8) | 0.00111 (4) | −0.00041 (5) | −0.00193 (4) |
F1 | 0.0264 (8) | 0.0196 (8) | 0.0147 (7) | 0.000 | 0.0038 (6) | 0.000 |
N1 | 0.0236 (8) | 0.0166 (8) | 0.0229 (8) | 0.0024 (6) | 0.0003 (6) | −0.0022 (6) |
C1 | 0.0213 (13) | 0.0242 (14) | 0.0166 (13) | 0.000 | −0.0005 (10) | 0.000 |
F2 | 0.0399 (7) | 0.0196 (6) | 0.0267 (6) | −0.0059 (5) | 0.0056 (5) | 0.0085 (5) |
N2 | 0.0237 (12) | 0.0239 (13) | 0.0208 (12) | 0.000 | 0.0036 (9) | 0.000 |
C2 | 0.0221 (9) | 0.0185 (10) | 0.0242 (10) | −0.0003 (8) | 0.0003 (7) | 0.0050 (8) |
F3 | 0.0274 (9) | 0.0356 (10) | 0.0178 (8) | 0.000 | 0.0066 (7) | 0.000 |
C3 | 0.0144 (12) | 0.0252 (14) | 0.0179 (13) | 0.000 | 0.0000 (10) | 0.000 |
C4 | 0.0172 (13) | 0.0325 (17) | 0.0234 (15) | 0.000 | −0.0007 (11) | 0.000 |
C5 | 0.0154 (13) | 0.0347 (16) | 0.0234 (15) | 0.000 | 0.0006 (10) | 0.000 |
C6 | 0.0143 (12) | 0.0347 (16) | 0.0189 (13) | 0.000 | 0.0022 (10) | 0.000 |
C7 | 0.0218 (10) | 0.0274 (11) | 0.0239 (10) | 0.0042 (8) | 0.0005 (8) | −0.0035 (8) |
C8 | 0.0218 (9) | 0.0258 (10) | 0.0224 (10) | 0.0033 (8) | 0.0003 (7) | 0.0015 (8) |
C9 | 0.0150 (12) | 0.0276 (15) | 0.0184 (13) | 0.000 | 0.0000 (10) | 0.000 |
C10 | 0.0307 (11) | 0.0282 (11) | 0.0246 (10) | −0.0037 (9) | 0.0072 (8) | 0.0018 (9) |
C11 | 0.0167 (12) | 0.0154 (12) | 0.0151 (11) | 0.000 | 0.0014 (9) | 0.000 |
C12 | 0.0176 (8) | 0.0116 (8) | 0.0202 (9) | 0.0003 (7) | −0.0001 (7) | −0.0012 (7) |
C13 | 0.0195 (9) | 0.0159 (9) | 0.0199 (9) | −0.0021 (7) | 0.0018 (7) | 0.0044 (7) |
C14 | 0.0163 (12) | 0.0235 (14) | 0.0168 (12) | 0.000 | 0.0035 (10) | 0.000 |
Geometric parameters (Å, º) top
I1—C12 | 2.0932 (18) | C5—C6 | 1.436 (4) |
F1—C11 | 1.357 (3) | C6—C7i | 1.398 (3) |
N1—C1 | 1.332 (2) | C6—C7 | 1.398 (3) |
N1—C2 | 1.336 (3) | C7—C8 | 1.386 (3) |
C1—H1 | 0.9500 | C7—H7 | 0.9500 |
F2—C13 | 1.338 (2) | C8—C9 | 1.410 (3) |
N2—C9 | 1.380 (4) | C8—H8 | 0.9500 |
N2—C10i | 1.459 (2) | C10—H10A | 0.9800 |
N2—C10 | 1.459 (2) | C10—H10B | 0.9800 |
C2—C3 | 1.393 (2) | C10—H10C | 0.9800 |
C2—H2 | 0.9500 | C11—C12ii | 1.383 (2) |
F3—C14 | 1.345 (3) | C11—C12 | 1.383 (2) |
C3—C4 | 1.430 (4) | C12—C13 | 1.386 (3) |
C4—C5 | 1.191 (4) | C13—C14 | 1.378 (2) |
| | | |
C1—N1—C2 | 116.46 (18) | C9—C8—H8 | 119.6 |
N1i—C1—N1 | 126.4 (3) | N2—C9—C8i | 121.18 (13) |
N1i—C1—H1 | 116.8 | N2—C9—C8 | 121.18 (13) |
N1—C1—H1 | 116.8 | C8i—C9—C8 | 117.6 (3) |
C9—N2—C10i | 118.53 (13) | N2—C10—H10A | 109.5 |
C9—N2—C10 | 118.53 (13) | N2—C10—H10B | 109.5 |
C10i—N2—C10 | 117.5 (2) | H10A—C10—H10B | 109.5 |
N1—C2—C3 | 122.47 (19) | N2—C10—H10C | 109.5 |
N1—C2—H2 | 118.8 | H10A—C10—H10C | 109.5 |
C3—C2—H2 | 118.8 | H10B—C10—H10C | 109.5 |
C2—C3—C2i | 115.8 (2) | F1—C11—C12ii | 118.21 (12) |
C2—C3—C4 | 122.11 (12) | F1—C11—C12 | 118.21 (12) |
C2i—C3—C4 | 122.11 (12) | C12ii—C11—C12 | 123.6 (2) |
C5—C4—C3 | 178.5 (3) | C11—C12—C13 | 116.94 (18) |
C4—C5—C6 | 178.1 (3) | C11—C12—I1 | 122.60 (15) |
C7i—C6—C7 | 118.1 (3) | C13—C12—I1 | 120.47 (14) |
C7i—C6—C5 | 120.90 (13) | F2—C13—C14 | 118.06 (17) |
C7—C6—C5 | 120.90 (13) | F2—C13—C12 | 120.21 (17) |
C8—C7—C6 | 121.2 (2) | C14—C13—C12 | 121.73 (18) |
C8—C7—H7 | 119.4 | F3—C14—C13 | 120.45 (12) |
C6—C7—H7 | 119.4 | F3—C14—C13ii | 120.45 (12) |
C7—C8—C9 | 120.9 (2) | C13—C14—C13ii | 119.1 (2) |
C7—C8—H8 | 119.6 | | |
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
2C14H13N3·2C6F4I2 | Z = 2 |
Mr = 1250.27 | F(000) = 1184 |
Triclinic, P1 | Dx = 1.978 Mg m−3 |
a = 9.1740 (7) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 14.0178 (10) Å | Cell parameters from 9917 reflections |
c = 17.5605 (13) Å | θ = 2.4–27.1° |
α = 100.065 (1)° | µ = 3.04 mm−1 |
β = 95.285 (1)° | T = 100 K |
γ = 107.225 (1)° | Cut, colourless |
V = 2098.8 (3) Å3 | 0.50 × 0.27 × 0.17 mm |
Data collection top
Bruker APEXII CCD diffractometer | 9224 independent reflections |
Radiation source: fine-focus sealed tube | 8375 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
Detector resolution: 8.3660 pixels mm-1 | θmax = 27.1°, θmin = 1.6° |
phi and ω scans | h = −11→11 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −17→17 |
Tmin = 0.394, Tmax = 0.589 | l = −22→22 |
26355 measured reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.021 | H-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 reflections | Δρmax = 0.99 e Å−3 |
527 parameters | Δρmin = −0.46 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 | 0.01383 (2) | 0.28785 (2) | 0.05480 (2) | 0.01866 (4) | |
F1 | −0.29851 (17) | 0.16750 (12) | −0.06022 (8) | 0.0234 (3) | |
N1 | 0.3243 (2) | 0.34365 (15) | 0.01771 (12) | 0.0166 (4) | |
C1 | 0.3477 (3) | 0.31927 (18) | −0.05610 (14) | 0.0186 (5) | |
H1 | 0.261144 | 0.281868 | −0.095103 | 0.022* | |
I2 | −0.65899 (2) | 0.05764 (2) | −0.07293 (2) | 0.01721 (4) | |
F2 | −0.66975 (16) | 0.13500 (12) | 0.11002 (9) | 0.0262 (3) | |
N2 | 0.5967 (2) | 0.42626 (16) | 0.05520 (12) | 0.0175 (4) | |
C2 | 0.4932 (3) | 0.34632 (19) | −0.07814 (15) | 0.0192 (5) | |
H2 | 0.508072 | 0.328417 | −0.130908 | 0.023* | |
I3 | 0.85764 (2) | 0.54755 (2) | 0.17666 (2) | 0.01709 (4) | |
F3 | −0.44678 (17) | 0.24057 (12) | 0.23158 (8) | 0.0257 (3) | |
N3 | 0.3471 (2) | 0.59644 (17) | 0.52730 (12) | 0.0201 (5) | |
C3 | 0.6155 (3) | 0.40069 (19) | −0.01934 (15) | 0.0195 (5) | |
H3 | 0.716849 | 0.420628 | −0.032422 | 0.023* | |
I4 | 1.12375 (2) | 0.78072 (2) | 0.51038 (2) | 0.01727 (4) | |
F4 | −0.14869 (17) | 0.30235 (11) | 0.21104 (8) | 0.0223 (3) | |
N4 | 1.0435 (2) | 0.83658 (16) | 0.66195 (12) | 0.0191 (4) | |
C4 | 0.4508 (3) | 0.39684 (18) | 0.07058 (14) | 0.0151 (5) | |
F5 | 0.88976 (15) | 0.65121 (11) | 0.35745 (8) | 0.0197 (3) | |
N5 | 1.1087 (2) | 0.92578 (16) | 0.79570 (12) | 0.0176 (4) | |
C5 | 0.4270 (3) | 0.42633 (19) | 0.14981 (14) | 0.0182 (5) | |
F6 | 1.42714 (16) | 0.81466 (11) | 0.42497 (9) | 0.0243 (3) | |
N6 | 2.0672 (2) | 1.09674 (17) | 0.67626 (13) | 0.0225 (5) | |
C6 | 0.4048 (3) | 0.45375 (19) | 0.21490 (15) | 0.0181 (5) | |
F7 | 1.46342 (16) | 0.75035 (13) | 0.27629 (9) | 0.0300 (4) | |
C7 | 0.3872 (3) | 0.48979 (19) | 0.29340 (14) | 0.0171 (5) | |
F8 | 1.21991 (17) | 0.63395 (13) | 0.16906 (9) | 0.0295 (4) | |
C8 | 0.2453 (3) | 0.45855 (19) | 0.32093 (15) | 0.0182 (5) | |
H8 | 0.156880 | 0.413356 | 0.286101 | 0.022* | |
C9 | 0.2326 (3) | 0.49255 (19) | 0.39781 (15) | 0.0174 (5) | |
H9 | 0.135732 | 0.469417 | 0.415193 | 0.021* | |
C10 | 0.3607 (3) | 0.56111 (18) | 0.45137 (14) | 0.0163 (5) | |
C11 | 0.5024 (3) | 0.59344 (19) | 0.42259 (14) | 0.0170 (5) | |
H11 | 0.590462 | 0.640473 | 0.456626 | 0.020* | |
C12 | 0.5146 (3) | 0.55782 (19) | 0.34612 (15) | 0.0189 (5) | |
H12 | 0.611577 | 0.579836 | 0.328622 | 0.023* | |
C13 | 0.2122 (3) | 0.5466 (2) | 0.56038 (16) | 0.0247 (6) | |
H13A | 0.122533 | 0.562652 | 0.538163 | 0.037* | |
H13B | 0.231471 | 0.571121 | 0.617317 | 0.037* | |
H13C | 0.191680 | 0.472456 | 0.547922 | 0.037* | |
C14 | 0.4766 (3) | 0.6724 (2) | 0.57970 (16) | 0.0261 (6) | |
H14A | 0.555727 | 0.641302 | 0.592697 | 0.039* | |
H14B | 0.441434 | 0.698360 | 0.627727 | 0.039* | |
H14C | 0.520342 | 0.728965 | 0.554120 | 0.039* | |
C15 | −0.2167 (3) | 0.23794 (18) | 0.07389 (14) | 0.0167 (5) | |
C16 | −0.3351 (3) | 0.18531 (18) | 0.01254 (14) | 0.0166 (5) | |
C17 | −0.4891 (3) | 0.14794 (18) | 0.02118 (14) | 0.0169 (5) | |
C18 | −0.5228 (3) | 0.16846 (19) | 0.09641 (15) | 0.0187 (5) | |
C19 | −0.4097 (3) | 0.22148 (19) | 0.15931 (14) | 0.0181 (5) | |
C20 | −0.2573 (3) | 0.25419 (18) | 0.14763 (14) | 0.0175 (5) | |
C21 | 1.0472 (3) | 0.63818 (18) | 0.26077 (14) | 0.0157 (5) | |
C22 | 1.0333 (3) | 0.67444 (18) | 0.33750 (14) | 0.0146 (5) | |
C23 | 1.1557 (3) | 0.73286 (18) | 0.39466 (14) | 0.0161 (5) | |
C24 | 1.3013 (3) | 0.75763 (19) | 0.37278 (15) | 0.0181 (5) | |
C25 | 1.3215 (3) | 0.7243 (2) | 0.29693 (15) | 0.0207 (5) | |
C26 | 1.1958 (3) | 0.66498 (19) | 0.24240 (15) | 0.0189 (5) | |
C27 | 0.8960 (3) | 0.80064 (19) | 0.67321 (15) | 0.0205 (5) | |
H27 | 0.821300 | 0.757305 | 0.630398 | 0.025* | |
C28 | 0.8489 (3) | 0.82401 (19) | 0.74399 (15) | 0.0206 (5) | |
H28 | 0.744305 | 0.797265 | 0.751160 | 0.025* | |
C29 | 0.9611 (3) | 0.88851 (19) | 0.80456 (15) | 0.0198 (5) | |
H29 | 0.931891 | 0.906848 | 0.854169 | 0.024* | |
C30 | 1.1437 (3) | 0.89742 (18) | 0.72425 (14) | 0.0154 (5) | |
C31 | 1.3025 (3) | 0.93454 (19) | 0.71349 (15) | 0.0189 (5) | |
C32 | 1.4343 (3) | 0.96259 (19) | 0.70317 (15) | 0.0189 (5) | |
C33 | 1.5941 (3) | 0.99660 (18) | 0.69455 (15) | 0.0180 (5) | |
C34 | 1.7046 (3) | 1.05532 (19) | 0.75934 (15) | 0.0192 (5) | |
H34 | 1.672190 | 1.071976 | 0.808392 | 0.023* | |
C35 | 1.8596 (3) | 1.08942 (19) | 0.75311 (15) | 0.0188 (5) | |
H35 | 1.931828 | 1.129748 | 0.797843 | 0.023* | |
C36 | 1.9126 (3) | 1.06565 (18) | 0.68200 (14) | 0.0163 (5) | |
C37 | 1.8002 (3) | 1.00715 (18) | 0.61632 (14) | 0.0172 (5) | |
H37 | 1.831828 | 0.990458 | 0.567090 | 0.021* | |
C38 | 1.6458 (3) | 0.97431 (18) | 0.62308 (14) | 0.0174 (5) | |
H38 | 1.572675 | 0.935640 | 0.578210 | 0.021* | |
C39 | 2.1782 (3) | 1.1623 (2) | 0.74254 (17) | 0.0272 (6) | |
H39A | 2.160272 | 1.228408 | 0.754727 | 0.041* | |
H39B | 2.282907 | 1.172574 | 0.729895 | 0.041* | |
H39C | 2.166861 | 1.130220 | 0.787920 | 0.041* | |
C40 | 2.1221 (3) | 1.0737 (2) | 0.60229 (15) | 0.0224 (6) | |
H40A | 2.083757 | 0.999716 | 0.581363 | 0.034* | |
H40B | 2.235292 | 1.097143 | 0.610735 | 0.034* | |
H40C | 2.084347 | 1.108584 | 0.564957 | 0.034* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.01293 (8) | 0.02075 (9) | 0.01951 (9) | 0.00233 (6) | 0.00128 (6) | 0.00298 (6) |
F1 | 0.0202 (8) | 0.0313 (9) | 0.0134 (7) | 0.0035 (7) | 0.0040 (6) | −0.0016 (6) |
N1 | 0.0149 (10) | 0.0174 (10) | 0.0158 (10) | 0.0043 (8) | −0.0001 (8) | 0.0019 (8) |
C1 | 0.0213 (13) | 0.0164 (12) | 0.0156 (12) | 0.0052 (10) | −0.0023 (10) | 0.0009 (10) |
I2 | 0.01488 (8) | 0.01587 (8) | 0.01746 (8) | 0.00258 (6) | −0.00194 (6) | 0.00105 (6) |
F2 | 0.0133 (7) | 0.0376 (9) | 0.0244 (8) | 0.0036 (7) | 0.0062 (6) | 0.0040 (7) |
N2 | 0.0157 (10) | 0.0169 (10) | 0.0170 (11) | 0.0029 (8) | 0.0022 (8) | 0.0002 (8) |
C2 | 0.0251 (14) | 0.0181 (12) | 0.0143 (12) | 0.0068 (10) | 0.0045 (10) | 0.0024 (10) |
I3 | 0.01489 (8) | 0.01655 (8) | 0.01638 (8) | 0.00303 (6) | −0.00064 (6) | −0.00043 (6) |
F3 | 0.0270 (8) | 0.0372 (9) | 0.0140 (8) | 0.0119 (7) | 0.0066 (6) | 0.0036 (7) |
N3 | 0.0169 (11) | 0.0270 (12) | 0.0135 (10) | 0.0047 (9) | 0.0037 (8) | 0.0002 (9) |
C3 | 0.0176 (13) | 0.0195 (13) | 0.0204 (13) | 0.0036 (10) | 0.0060 (10) | 0.0036 (10) |
I4 | 0.01797 (8) | 0.01846 (8) | 0.01424 (8) | 0.00583 (6) | 0.00058 (6) | 0.00149 (6) |
F4 | 0.0208 (8) | 0.0262 (8) | 0.0152 (7) | 0.0050 (6) | −0.0044 (6) | 0.0004 (6) |
N4 | 0.0159 (11) | 0.0202 (11) | 0.0180 (11) | 0.0023 (9) | 0.0020 (8) | 0.0023 (9) |
C4 | 0.0171 (12) | 0.0132 (11) | 0.0135 (12) | 0.0032 (9) | 0.0007 (9) | 0.0024 (9) |
F5 | 0.0110 (7) | 0.0281 (8) | 0.0176 (7) | 0.0027 (6) | 0.0046 (6) | 0.0032 (6) |
N5 | 0.0154 (10) | 0.0189 (11) | 0.0165 (11) | 0.0029 (8) | 0.0026 (8) | 0.0033 (8) |
C5 | 0.0148 (12) | 0.0207 (13) | 0.0167 (13) | 0.0042 (10) | 0.0002 (10) | 0.0015 (10) |
F6 | 0.0137 (7) | 0.0272 (8) | 0.0230 (8) | −0.0011 (6) | −0.0039 (6) | −0.0016 (7) |
N6 | 0.0136 (11) | 0.0278 (12) | 0.0200 (11) | 0.0009 (9) | 0.0053 (9) | −0.0015 (9) |
C6 | 0.0143 (12) | 0.0195 (13) | 0.0198 (13) | 0.0050 (10) | 0.0009 (10) | 0.0039 (10) |
F7 | 0.0116 (7) | 0.0431 (10) | 0.0305 (9) | 0.0023 (7) | 0.0089 (7) | 0.0032 (8) |
C7 | 0.0174 (12) | 0.0181 (12) | 0.0152 (12) | 0.0060 (10) | 0.0019 (10) | 0.0014 (10) |
F8 | 0.0210 (8) | 0.0424 (10) | 0.0193 (8) | 0.0057 (7) | 0.0064 (6) | −0.0025 (7) |
C8 | 0.0121 (12) | 0.0176 (12) | 0.0203 (13) | 0.0011 (10) | −0.0017 (10) | 0.0010 (10) |
C9 | 0.0118 (11) | 0.0219 (13) | 0.0180 (12) | 0.0038 (10) | 0.0037 (9) | 0.0048 (10) |
C10 | 0.0177 (12) | 0.0166 (12) | 0.0153 (12) | 0.0078 (10) | 0.0019 (10) | 0.0011 (10) |
C11 | 0.0122 (11) | 0.0200 (12) | 0.0154 (12) | 0.0021 (10) | −0.0006 (9) | 0.0014 (10) |
C12 | 0.0113 (11) | 0.0244 (13) | 0.0193 (13) | 0.0043 (10) | 0.0017 (10) | 0.0031 (11) |
C13 | 0.0249 (14) | 0.0300 (15) | 0.0204 (14) | 0.0088 (12) | 0.0084 (11) | 0.0060 (11) |
C14 | 0.0235 (14) | 0.0307 (15) | 0.0175 (13) | 0.0042 (12) | −0.0002 (11) | −0.0029 (11) |
C15 | 0.0142 (12) | 0.0167 (12) | 0.0187 (12) | 0.0042 (10) | 0.0027 (10) | 0.0038 (10) |
C16 | 0.0178 (12) | 0.0169 (12) | 0.0142 (12) | 0.0042 (10) | 0.0023 (10) | 0.0032 (10) |
C17 | 0.0174 (12) | 0.0160 (12) | 0.0156 (12) | 0.0055 (10) | −0.0019 (10) | 0.0008 (10) |
C18 | 0.0137 (12) | 0.0216 (13) | 0.0220 (13) | 0.0061 (10) | 0.0050 (10) | 0.0058 (11) |
C19 | 0.0208 (13) | 0.0225 (13) | 0.0128 (12) | 0.0086 (11) | 0.0048 (10) | 0.0036 (10) |
C20 | 0.0168 (12) | 0.0175 (12) | 0.0155 (12) | 0.0049 (10) | −0.0041 (10) | 0.0008 (10) |
C21 | 0.0134 (11) | 0.0174 (12) | 0.0148 (12) | 0.0037 (10) | 0.0001 (9) | 0.0027 (10) |
C22 | 0.0097 (11) | 0.0167 (12) | 0.0167 (12) | 0.0026 (9) | 0.0018 (9) | 0.0048 (10) |
C23 | 0.0156 (12) | 0.0167 (12) | 0.0153 (12) | 0.0043 (10) | 0.0022 (9) | 0.0028 (10) |
C24 | 0.0117 (11) | 0.0178 (12) | 0.0203 (13) | 0.0009 (10) | −0.0035 (10) | 0.0015 (10) |
C25 | 0.0121 (12) | 0.0238 (13) | 0.0249 (14) | 0.0029 (10) | 0.0062 (10) | 0.0053 (11) |
C26 | 0.0170 (12) | 0.0230 (13) | 0.0164 (12) | 0.0067 (10) | 0.0050 (10) | 0.0018 (10) |
C27 | 0.0144 (12) | 0.0211 (13) | 0.0207 (13) | 0.0001 (10) | −0.0013 (10) | 0.0023 (11) |
C28 | 0.0122 (12) | 0.0228 (13) | 0.0245 (14) | 0.0015 (10) | 0.0029 (10) | 0.0062 (11) |
C29 | 0.0197 (13) | 0.0216 (13) | 0.0185 (13) | 0.0057 (11) | 0.0062 (10) | 0.0049 (10) |
C30 | 0.0140 (12) | 0.0156 (12) | 0.0153 (12) | 0.0026 (9) | 0.0014 (9) | 0.0038 (9) |
C31 | 0.0165 (13) | 0.0203 (13) | 0.0167 (12) | 0.0028 (10) | 0.0011 (10) | 0.0016 (10) |
C32 | 0.0171 (13) | 0.0178 (12) | 0.0184 (13) | 0.0022 (10) | 0.0005 (10) | 0.0024 (10) |
C33 | 0.0173 (12) | 0.0164 (12) | 0.0193 (13) | 0.0034 (10) | 0.0042 (10) | 0.0039 (10) |
C34 | 0.0185 (13) | 0.0227 (13) | 0.0147 (12) | 0.0054 (10) | 0.0040 (10) | 0.0008 (10) |
C35 | 0.0168 (12) | 0.0200 (13) | 0.0155 (12) | 0.0024 (10) | 0.0010 (10) | −0.0003 (10) |
C36 | 0.0136 (12) | 0.0148 (12) | 0.0190 (12) | 0.0018 (9) | 0.0027 (10) | 0.0043 (10) |
C37 | 0.0185 (12) | 0.0179 (12) | 0.0146 (12) | 0.0055 (10) | 0.0037 (10) | 0.0020 (10) |
C38 | 0.0157 (12) | 0.0164 (12) | 0.0164 (12) | 0.0016 (10) | −0.0010 (10) | 0.0020 (10) |
C39 | 0.0140 (13) | 0.0300 (15) | 0.0283 (15) | −0.0002 (11) | 0.0015 (11) | −0.0047 (12) |
C40 | 0.0165 (13) | 0.0295 (15) | 0.0239 (14) | 0.0083 (11) | 0.0078 (11) | 0.0085 (11) |
Geometric parameters (Å, º) top
I1—C15 | 2.101 (2) | C12—H12 | 0.9500 |
F1—C16 | 1.351 (3) | C13—H13A | 0.9800 |
N1—C1 | 1.335 (3) | C13—H13B | 0.9800 |
N1—C4 | 1.346 (3) | C13—H13C | 0.9800 |
C1—C2 | 1.386 (4) | C14—H14A | 0.9800 |
C1—H1 | 0.9500 | C14—H14B | 0.9800 |
I2—C17 | 2.095 (2) | C14—H14C | 0.9800 |
F2—C18 | 1.349 (3) | C15—C20 | 1.380 (3) |
N2—C3 | 1.336 (3) | C15—C16 | 1.384 (3) |
N2—C4 | 1.346 (3) | C16—C17 | 1.386 (3) |
C2—C3 | 1.383 (4) | C17—C18 | 1.385 (3) |
C2—H2 | 0.9500 | C18—C19 | 1.376 (4) |
I3—C21 | 2.094 (2) | C19—C20 | 1.383 (3) |
F3—C19 | 1.346 (3) | C21—C22 | 1.386 (3) |
N3—C10 | 1.369 (3) | C21—C26 | 1.387 (3) |
N3—C14 | 1.449 (3) | C22—C23 | 1.378 (3) |
N3—C13 | 1.456 (3) | C23—C24 | 1.385 (3) |
C3—H3 | 0.9500 | C24—C25 | 1.381 (4) |
I4—C23 | 2.101 (2) | C25—C26 | 1.374 (4) |
F4—C20 | 1.350 (3) | C27—C28 | 1.371 (4) |
N4—C30 | 1.339 (3) | C27—H27 | 0.9500 |
N4—C27 | 1.344 (3) | C28—C29 | 1.386 (4) |
C4—C5 | 1.436 (3) | C28—H28 | 0.9500 |
F5—C22 | 1.354 (3) | C29—H29 | 0.9500 |
N5—C29 | 1.334 (3) | C30—C31 | 1.437 (3) |
N5—C30 | 1.346 (3) | C31—C32 | 1.196 (3) |
C5—C6 | 1.196 (3) | C32—C33 | 1.433 (3) |
F6—C24 | 1.347 (3) | C33—C38 | 1.399 (3) |
N6—C36 | 1.373 (3) | C33—C34 | 1.402 (3) |
N6—C39 | 1.446 (3) | C34—C35 | 1.382 (3) |
N6—C40 | 1.455 (3) | C34—H34 | 0.9500 |
C6—C7 | 1.424 (3) | C35—C36 | 1.403 (3) |
F7—C25 | 1.346 (3) | C35—H35 | 0.9500 |
C7—C12 | 1.401 (3) | C36—C37 | 1.420 (3) |
C7—C8 | 1.404 (3) | C37—C38 | 1.377 (3) |
F8—C26 | 1.345 (3) | C37—H37 | 0.9500 |
C8—C9 | 1.378 (3) | C38—H38 | 0.9500 |
C8—H8 | 0.9500 | C39—H39A | 0.9800 |
C9—C10 | 1.414 (3) | C39—H39B | 0.9800 |
C9—H9 | 0.9500 | C39—H39C | 0.9800 |
C10—C11 | 1.415 (3) | C40—H40A | 0.9800 |
C11—C12 | 1.375 (3) | C40—H40B | 0.9800 |
C11—H11 | 0.9500 | C40—H40C | 0.9800 |
| | | |
C1—N1—C4 | 116.2 (2) | F3—C19—C20 | 120.3 (2) |
N1—C1—C2 | 122.7 (2) | C18—C19—C20 | 119.3 (2) |
N1—C1—H1 | 118.7 | F4—C20—C15 | 120.8 (2) |
C2—C1—H1 | 118.7 | F4—C20—C19 | 117.8 (2) |
C3—N2—C4 | 116.4 (2) | C15—C20—C19 | 121.4 (2) |
C3—C2—C1 | 116.5 (2) | C22—C21—C26 | 116.0 (2) |
C3—C2—H2 | 121.7 | C22—C21—I3 | 122.78 (17) |
C1—C2—H2 | 121.7 | C26—C21—I3 | 121.25 (18) |
C10—N3—C14 | 120.6 (2) | F5—C22—C23 | 117.9 (2) |
C10—N3—C13 | 120.4 (2) | F5—C22—C21 | 117.7 (2) |
C14—N3—C13 | 118.3 (2) | C23—C22—C21 | 124.3 (2) |
N2—C3—C2 | 122.5 (2) | C22—C23—C24 | 117.1 (2) |
N2—C3—H3 | 118.8 | C22—C23—I4 | 121.55 (17) |
C2—C3—H3 | 118.8 | C24—C23—I4 | 121.33 (18) |
C30—N4—C27 | 116.1 (2) | F6—C24—C25 | 118.2 (2) |
N1—C4—N2 | 125.6 (2) | F6—C24—C23 | 120.9 (2) |
N1—C4—C5 | 116.9 (2) | C25—C24—C23 | 120.9 (2) |
N2—C4—C5 | 117.5 (2) | F7—C25—C26 | 120.1 (2) |
C29—N5—C30 | 116.3 (2) | F7—C25—C24 | 120.2 (2) |
C6—C5—C4 | 177.4 (3) | C26—C25—C24 | 119.7 (2) |
C36—N6—C39 | 120.1 (2) | F8—C26—C25 | 118.0 (2) |
C36—N6—C40 | 121.5 (2) | F8—C26—C21 | 120.0 (2) |
C39—N6—C40 | 118.1 (2) | C25—C26—C21 | 122.0 (2) |
C5—C6—C7 | 176.8 (3) | N4—C27—C28 | 122.6 (2) |
C12—C7—C8 | 118.0 (2) | N4—C27—H27 | 118.7 |
C12—C7—C6 | 119.9 (2) | C28—C27—H27 | 118.7 |
C8—C7—C6 | 122.2 (2) | C27—C28—C29 | 116.8 (2) |
C9—C8—C7 | 120.9 (2) | C27—C28—H28 | 121.6 |
C9—C8—H8 | 119.5 | C29—C28—H28 | 121.6 |
C7—C8—H8 | 119.5 | N5—C29—C28 | 122.4 (2) |
C8—C9—C10 | 121.5 (2) | N5—C29—H29 | 118.8 |
C8—C9—H9 | 119.3 | C28—C29—H29 | 118.8 |
C10—C9—H9 | 119.3 | N4—C30—N5 | 125.8 (2) |
N3—C10—C9 | 121.4 (2) | N4—C30—C31 | 116.7 (2) |
N3—C10—C11 | 121.5 (2) | N5—C30—C31 | 117.6 (2) |
C9—C10—C11 | 117.1 (2) | C32—C31—C30 | 178.0 (3) |
C12—C11—C10 | 121.0 (2) | C31—C32—C33 | 177.4 (3) |
C12—C11—H11 | 119.5 | C38—C33—C34 | 117.9 (2) |
C10—C11—H11 | 119.5 | C38—C33—C32 | 122.5 (2) |
C11—C12—C7 | 121.5 (2) | C34—C33—C32 | 119.6 (2) |
C11—C12—H12 | 119.2 | C35—C34—C33 | 121.1 (2) |
C7—C12—H12 | 119.2 | C35—C34—H34 | 119.4 |
N3—C13—H13A | 109.5 | C33—C34—H34 | 119.4 |
N3—C13—H13B | 109.5 | C34—C35—C36 | 121.3 (2) |
H13A—C13—H13B | 109.5 | C34—C35—H35 | 119.4 |
N3—C13—H13C | 109.5 | C36—C35—H35 | 119.4 |
H13A—C13—H13C | 109.5 | N6—C36—C35 | 121.4 (2) |
H13B—C13—H13C | 109.5 | N6—C36—C37 | 121.3 (2) |
N3—C14—H14A | 109.5 | C35—C36—C37 | 117.3 (2) |
N3—C14—H14B | 109.5 | C38—C37—C36 | 120.8 (2) |
H14A—C14—H14B | 109.5 | C38—C37—H37 | 119.6 |
N3—C14—H14C | 109.5 | C36—C37—H37 | 119.6 |
H14A—C14—H14C | 109.5 | C37—C38—C33 | 121.5 (2) |
H14B—C14—H14C | 109.5 | C37—C38—H38 | 119.3 |
C20—C15—C16 | 116.9 (2) | C33—C38—H38 | 119.3 |
C20—C15—I1 | 122.01 (18) | N6—C39—H39A | 109.5 |
C16—C15—I1 | 121.06 (18) | N6—C39—H39B | 109.5 |
F1—C16—C15 | 118.2 (2) | H39A—C39—H39B | 109.5 |
F1—C16—C17 | 117.7 (2) | N6—C39—H39C | 109.5 |
C15—C16—C17 | 124.1 (2) | H39A—C39—H39C | 109.5 |
C18—C17—C16 | 116.2 (2) | H39B—C39—H39C | 109.5 |
C18—C17—I2 | 121.82 (18) | N6—C40—H40A | 109.5 |
C16—C17—I2 | 121.83 (18) | N6—C40—H40B | 109.5 |
F2—C18—C19 | 117.9 (2) | H40A—C40—H40B | 109.5 |
F2—C18—C17 | 120.1 (2) | N6—C40—H40C | 109.5 |
C19—C18—C17 | 122.0 (2) | H40A—C40—H40C | 109.5 |
F3—C19—C18 | 120.4 (2) | H40B—C40—H40C | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···F8i | 0.95 | 2.57 | 3.170 (3) | 121 |
C3—H3···F8i | 0.95 | 2.56 | 3.185 (3) | 124 |
C13—H13A···I4ii | 0.98 | 3.18 | 3.828 (3) | 125 |
C13—H13C···F5iii | 0.98 | 2.61 | 3.280 (3) | 126 |
C14—H14B···F3iv | 0.98 | 2.46 | 3.391 (3) | 158 |
C29—H29···F2iv | 0.95 | 2.47 | 3.145 (3) | 128 |
C39—H39A···I3v | 0.98 | 3.22 | 4.187 (3) | 170 |
C39—H39B···F7vi | 0.98 | 2.28 | 3.221 (3) | 161 |
C39—H39C···I2vii | 0.98 | 3.27 | 4.117 (3) | 146 |
C40—H40A···I4viii | 0.98 | 3.24 | 4.146 (3) | 154 |
C40—H40C···I4v | 0.98 | 3.13 | 4.060 (3) | 159 |
Symmetry codes: (i) −x+2, −y+1, −z; (ii) x−1, 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·C6F4I2 | Z = 2 |
Mr = 625.13 | F(000) = 592 |
Triclinic, P1 | Dx = 1.957 Mg m−3 |
a = 9.3688 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.4346 (7) Å | Cell parameters from 9177 reflections |
c = 12.0797 (7) Å | θ = 2.3–27.1° |
α = 62.075 (1)° | µ = 3.01 mm−1 |
β = 82.310 (1)° | T = 100 K |
γ = 68.234 (1)° | Cut, colourless |
V = 1060.63 (11) Å3 | 0.38 × 0.18 × 0.10 mm |
Data collection top
Bruker APEXII CCD diffractometer | 4679 independent reflections |
Radiation source: fine-focus sealed tube | 4312 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.014 |
Detector resolution: 8.3660 pixels mm-1 | θmax = 27.1°, θmin = 1.9° |
phi and ω scans | h = −11→11 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −14→14 |
Tmin = 0.527, Tmax = 0.740 | l = −15→15 |
13784 measured reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.020 | H-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 reflections | Δρmax = 1.44 e Å−3 |
264 parameters | Δρmin = −0.61 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 | 0.22187 (2) | 1.06411 (2) | 0.72486 (2) | 0.01787 (5) | |
F1 | −0.17435 (16) | 1.58998 (14) | 0.64783 (13) | 0.0235 (3) | |
N1 | 0.4842 (2) | 0.8055 (2) | 0.84647 (19) | 0.0209 (4) | |
C1 | 0.5097 (3) | 0.6930 (2) | 0.8286 (2) | 0.0203 (5) | |
H1 | 0.447273 | 0.701909 | 0.767267 | 0.024* | |
I2 | 0.12511 (2) | 1.35300 (2) | 0.81081 (2) | 0.01766 (5) | |
F2 | −0.36196 (17) | 1.60429 (15) | 0.49033 (14) | 0.0305 (3) | |
N2 | 0.6888 (2) | 0.6694 (2) | 1.00246 (19) | 0.0210 (4) | |
C2 | 0.5751 (3) | 0.7878 (2) | 0.9331 (2) | 0.0214 (5) | |
H2 | 0.557100 | 0.867299 | 0.946777 | 0.026* | |
F3 | −0.29595 (17) | 1.38803 (16) | 0.43050 (13) | 0.0287 (3) | |
N3 | 0.7907 (2) | −0.0955 (2) | 0.72789 (19) | 0.0208 (4) | |
C3 | 0.7120 (3) | 0.5580 (2) | 0.9832 (2) | 0.0210 (5) | |
H3 | 0.792126 | 0.471780 | 1.031013 | 0.025* | |
F4 | −0.04156 (16) | 1.15776 (15) | 0.53062 (13) | 0.0241 (3) | |
C4 | 0.6238 (3) | 0.5630 (2) | 0.8961 (2) | 0.0176 (4) | |
C5 | 0.6472 (3) | 0.4423 (2) | 0.8780 (2) | 0.0199 (5) | |
C6 | 0.6648 (3) | 0.3425 (2) | 0.8616 (2) | 0.0190 (4) | |
C7 | 0.6900 (3) | 0.2267 (2) | 0.8354 (2) | 0.0177 (4) | |
C8 | 0.8143 (3) | 0.1001 (2) | 0.8922 (2) | 0.0195 (5) | |
H8 | 0.877407 | 0.087326 | 0.955221 | 0.023* | |
C9 | 0.8473 (3) | −0.0068 (2) | 0.8584 (2) | 0.0188 (4) | |
H9 | 0.932124 | −0.091979 | 0.898632 | 0.023* | |
C10 | 0.7563 (3) | 0.0091 (2) | 0.7647 (2) | 0.0177 (4) | |
C11 | 0.6279 (3) | 0.1343 (2) | 0.7116 (2) | 0.0191 (4) | |
H11 | 0.562314 | 0.146221 | 0.650616 | 0.023* | |
C12 | 0.5955 (3) | 0.2405 (2) | 0.7466 (2) | 0.0194 (5) | |
H12 | 0.507748 | 0.323902 | 0.709723 | 0.023* | |
C13 | 0.9382 (3) | −0.2114 (3) | 0.7686 (3) | 0.0268 (5) | |
H13A | 1.021750 | −0.173646 | 0.737547 | 0.040* | |
H13B | 0.945387 | −0.276590 | 0.735105 | 0.040* | |
H13C | 0.946771 | −0.262087 | 0.860418 | 0.040* | |
C14 | 0.7166 (3) | −0.0627 (3) | 0.6131 (2) | 0.0260 (5) | |
H14A | 0.604916 | −0.034084 | 0.621028 | 0.039* | |
H14B | 0.753706 | −0.146515 | 0.598864 | 0.039* | |
H14C | 0.741468 | 0.014673 | 0.542111 | 0.039* | |
C15 | 0.0283 (2) | 1.2500 (2) | 0.6468 (2) | 0.0164 (4) | |
C16 | −0.0068 (3) | 1.3611 (2) | 0.6781 (2) | 0.0165 (4) | |
C17 | −0.1368 (3) | 1.4791 (2) | 0.6224 (2) | 0.0177 (4) | |
C18 | −0.2346 (3) | 1.4895 (2) | 0.5400 (2) | 0.0206 (5) | |
C19 | −0.2006 (3) | 1.3799 (3) | 0.5095 (2) | 0.0209 (5) | |
C20 | −0.0697 (3) | 1.2625 (2) | 0.5627 (2) | 0.0189 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.01696 (8) | 0.01741 (8) | 0.01916 (8) | −0.00427 (6) | 0.00035 (5) | −0.00947 (6) |
F1 | 0.0265 (7) | 0.0156 (6) | 0.0248 (7) | −0.0044 (6) | 0.0007 (6) | −0.0086 (6) |
N1 | 0.0224 (10) | 0.0165 (9) | 0.0227 (10) | −0.0055 (8) | 0.0008 (8) | −0.0089 (8) |
C1 | 0.0224 (12) | 0.0218 (11) | 0.0188 (11) | −0.0079 (9) | −0.0012 (9) | −0.0102 (9) |
I2 | 0.02004 (8) | 0.01798 (8) | 0.01638 (8) | −0.00698 (6) | −0.00079 (5) | −0.00828 (6) |
F2 | 0.0247 (8) | 0.0243 (7) | 0.0300 (8) | 0.0004 (6) | −0.0102 (6) | −0.0065 (6) |
N2 | 0.0235 (10) | 0.0218 (10) | 0.0218 (10) | −0.0096 (8) | 0.0008 (8) | −0.0118 (8) |
C2 | 0.0241 (12) | 0.0192 (11) | 0.0261 (12) | −0.0104 (10) | 0.0060 (10) | −0.0134 (10) |
F3 | 0.0273 (8) | 0.0361 (8) | 0.0236 (7) | −0.0131 (7) | −0.0075 (6) | −0.0105 (6) |
N3 | 0.0242 (10) | 0.0177 (9) | 0.0206 (10) | −0.0050 (8) | −0.0006 (8) | −0.0101 (8) |
C3 | 0.0199 (11) | 0.0191 (11) | 0.0221 (11) | −0.0046 (9) | −0.0008 (9) | −0.0092 (9) |
F4 | 0.0252 (7) | 0.0291 (8) | 0.0262 (7) | −0.0099 (6) | 0.0007 (6) | −0.0184 (6) |
C4 | 0.0196 (11) | 0.0186 (11) | 0.0182 (11) | −0.0084 (9) | 0.0054 (9) | −0.0111 (9) |
C5 | 0.0193 (11) | 0.0208 (11) | 0.0205 (11) | −0.0064 (9) | 0.0031 (9) | −0.0112 (9) |
C6 | 0.0187 (11) | 0.0212 (11) | 0.0157 (10) | −0.0075 (9) | 0.0027 (8) | −0.0075 (9) |
C7 | 0.0186 (11) | 0.0183 (11) | 0.0176 (11) | −0.0074 (9) | 0.0051 (9) | −0.0097 (9) |
C8 | 0.0206 (11) | 0.0208 (11) | 0.0174 (11) | −0.0084 (9) | −0.0017 (9) | −0.0075 (9) |
C9 | 0.0174 (11) | 0.0145 (10) | 0.0201 (11) | −0.0027 (9) | −0.0009 (9) | −0.0061 (9) |
C10 | 0.0199 (11) | 0.0164 (10) | 0.0176 (10) | −0.0089 (9) | 0.0042 (9) | −0.0073 (9) |
C11 | 0.0189 (11) | 0.0195 (11) | 0.0189 (11) | −0.0057 (9) | −0.0034 (9) | −0.0085 (9) |
C12 | 0.0178 (11) | 0.0155 (10) | 0.0213 (11) | −0.0032 (9) | −0.0009 (9) | −0.0071 (9) |
C13 | 0.0258 (13) | 0.0221 (12) | 0.0339 (14) | −0.0051 (10) | 0.0025 (11) | −0.0166 (11) |
C14 | 0.0324 (14) | 0.0258 (13) | 0.0252 (12) | −0.0102 (11) | 0.0016 (10) | −0.0159 (11) |
C15 | 0.0163 (10) | 0.0170 (10) | 0.0141 (10) | −0.0053 (8) | 0.0009 (8) | −0.0060 (8) |
C16 | 0.0177 (11) | 0.0180 (11) | 0.0140 (10) | −0.0086 (9) | 0.0005 (8) | −0.0056 (9) |
C17 | 0.0188 (11) | 0.0150 (10) | 0.0162 (10) | −0.0063 (9) | 0.0030 (8) | −0.0049 (9) |
C18 | 0.0174 (11) | 0.0178 (11) | 0.0169 (11) | −0.0031 (9) | −0.0024 (9) | −0.0019 (9) |
C19 | 0.0204 (11) | 0.0275 (12) | 0.0148 (10) | −0.0126 (10) | −0.0013 (9) | −0.0059 (9) |
C20 | 0.0205 (11) | 0.0238 (11) | 0.0164 (10) | −0.0119 (9) | 0.0045 (9) | −0.0101 (9) |
Geometric parameters (Å, º) top
I1—C15 | 2.102 (2) | C7—C8 | 1.399 (3) |
F1—C17 | 1.354 (3) | C8—C9 | 1.383 (3) |
N1—C2 | 1.331 (3) | C8—H8 | 0.9500 |
N1—C1 | 1.333 (3) | C9—C10 | 1.410 (3) |
C1—C4 | 1.392 (3) | C9—H9 | 0.9500 |
C1—H1 | 0.9500 | C10—C11 | 1.406 (3) |
I2—C16 | 2.100 (2) | C11—C12 | 1.386 (3) |
F2—C18 | 1.341 (3) | C11—H11 | 0.9500 |
N2—C2 | 1.333 (3) | C12—H12 | 0.9500 |
N2—C3 | 1.335 (3) | C13—H13A | 0.9800 |
C2—H2 | 0.9500 | C13—H13B | 0.9800 |
F3—C19 | 1.342 (3) | C13—H13C | 0.9800 |
N3—C10 | 1.381 (3) | C14—H14A | 0.9800 |
N3—C13 | 1.456 (3) | C14—H14B | 0.9800 |
N3—C14 | 1.457 (3) | C14—H14C | 0.9800 |
C3—C4 | 1.392 (3) | C15—C20 | 1.383 (3) |
C3—H3 | 0.9500 | C15—C16 | 1.405 (3) |
F4—C20 | 1.352 (3) | C16—C17 | 1.381 (3) |
C4—C5 | 1.431 (3) | C17—C18 | 1.377 (3) |
C5—C6 | 1.197 (3) | C18—C19 | 1.382 (3) |
C6—C7 | 1.432 (3) | C19—C20 | 1.379 (3) |
C7—C12 | 1.397 (3) | | |
| | | |
C2—N1—C1 | 116.3 (2) | C11—C12—C7 | 121.0 (2) |
N1—C1—C4 | 122.8 (2) | C11—C12—H12 | 119.5 |
N1—C1—H1 | 118.6 | C7—C12—H12 | 119.5 |
C4—C1—H1 | 118.6 | N3—C13—H13A | 109.5 |
C2—N2—C3 | 116.3 (2) | N3—C13—H13B | 109.5 |
N1—C2—N2 | 126.4 (2) | H13A—C13—H13B | 109.5 |
N1—C2—H2 | 116.8 | N3—C13—H13C | 109.5 |
N2—C2—H2 | 116.8 | H13A—C13—H13C | 109.5 |
C10—N3—C13 | 119.2 (2) | H13B—C13—H13C | 109.5 |
C10—N3—C14 | 119.05 (19) | N3—C14—H14A | 109.5 |
C13—N3—C14 | 116.9 (2) | N3—C14—H14B | 109.5 |
N2—C3—C4 | 122.7 (2) | H14A—C14—H14B | 109.5 |
N2—C3—H3 | 118.7 | N3—C14—H14C | 109.5 |
C4—C3—H3 | 118.7 | H14A—C14—H14C | 109.5 |
C1—C4—C3 | 115.5 (2) | H14B—C14—H14C | 109.5 |
C1—C4—C5 | 122.1 (2) | C20—C15—C16 | 118.7 (2) |
C3—C4—C5 | 122.4 (2) | C20—C15—I1 | 118.66 (17) |
C6—C5—C4 | 179.0 (3) | C16—C15—I1 | 122.63 (16) |
C5—C6—C7 | 176.7 (2) | C17—C16—C15 | 118.5 (2) |
C12—C7—C8 | 118.2 (2) | C17—C16—I2 | 118.46 (16) |
C12—C7—C6 | 120.5 (2) | C15—C16—I2 | 122.97 (16) |
C8—C7—C6 | 121.2 (2) | F1—C17—C18 | 116.9 (2) |
C9—C8—C7 | 121.3 (2) | F1—C17—C16 | 120.9 (2) |
C9—C8—H8 | 119.4 | C18—C17—C16 | 122.2 (2) |
C7—C8—H8 | 119.4 | F2—C18—C17 | 120.4 (2) |
C8—C9—C10 | 120.8 (2) | F2—C18—C19 | 120.3 (2) |
C8—C9—H9 | 119.6 | C17—C18—C19 | 119.2 (2) |
C10—C9—H9 | 119.6 | F3—C19—C20 | 120.9 (2) |
N3—C10—C11 | 121.1 (2) | F3—C19—C18 | 119.9 (2) |
N3—C10—C9 | 121.2 (2) | C20—C19—C18 | 119.2 (2) |
C11—C10—C9 | 117.7 (2) | F4—C20—C19 | 117.1 (2) |
C12—C11—C10 | 121.1 (2) | F4—C20—C15 | 120.8 (2) |
C12—C11—H11 | 119.5 | C19—C20—C15 | 122.0 (2) |
C10—C11—H11 | 119.5 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···F2i | 0.95 | 2.63 | 3.220 (3) | 121 |
C14—H14B···F1ii | 0.98 | 2.61 | 3.541 (3) | 159 |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) x+1, y−2, 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·C6H6 | F(000) = 1352 |
Mr = 703.24 | Dx = 1.852 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 7.2512 (6) Å | Cell parameters from 7881 reflections |
b = 20.6215 (17) Å | θ = 2.3–27.1° |
c = 17.1906 (14) Å | µ = 2.54 mm−1 |
β = 101.166 (1)° | T = 100 K |
V = 2521.9 (4) Å3 | Cut block, colourless |
Z = 4 | 0.40 × 0.25 × 0.04 mm |
Data collection top
Bruker APEXII CCD diffractometer | 5618 independent reflections |
Radiation source: fine-focus sealed tube | 4701 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
Detector resolution: 8.3660 pixels mm-1 | θmax = 27.2°, θmin = 2.0° |
phi and ω scans | h = −9→9 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −26→26 |
Tmin = 0.471, Tmax = 0.903 | l = −22→22 |
28632 measured reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.032 | H-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 reflections | Δρmax = 1.93 e Å−3 |
318 parameters | Δρmin = −0.44 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 | 0.74810 (3) | 0.58944 (2) | 0.35906 (2) | 0.02079 (7) | |
F1 | 0.8779 (3) | 0.53503 (10) | 0.67688 (11) | 0.0262 (5) | |
N1 | 0.7641 (4) | 0.65935 (14) | 0.21470 (16) | 0.0247 (7) | |
C1 | 0.9069 (5) | 0.64382 (18) | 0.1799 (2) | 0.0299 (9) | |
H1 | 0.998608 | 0.614018 | 0.205725 | 0.036* | |
I2 | 0.93280 (3) | 0.64921 (2) | 0.56357 (2) | 0.02015 (7) | |
F2 | 0.7492 (3) | 0.41418 (9) | 0.65467 (11) | 0.0251 (5) | |
N2 | 0.6419 (4) | 0.72863 (14) | 0.10478 (16) | 0.0257 (7) | |
C2 | 0.9269 (5) | 0.66945 (19) | 0.1074 (2) | 0.0302 (8) | |
H2 | 1.030179 | 0.658373 | 0.083428 | 0.036* | |
F3 | 0.6133 (3) | 0.36921 (9) | 0.50499 (12) | 0.0273 (5) | |
N3 | −0.2691 (4) | 0.83280 (15) | 0.35686 (16) | 0.0260 (7) | |
C3 | 0.7892 (5) | 0.71178 (18) | 0.0722 (2) | 0.0300 (8) | |
H3 | 0.798624 | 0.730006 | 0.022341 | 0.036* | |
F4 | 0.6131 (3) | 0.44633 (9) | 0.37948 (11) | 0.0259 (4) | |
C4 | 0.6367 (5) | 0.70149 (16) | 0.17603 (19) | 0.0223 (7) | |
C5 | 0.4841 (5) | 0.71971 (17) | 0.21178 (19) | 0.0246 (8) | |
C6 | 0.3540 (5) | 0.73840 (16) | 0.2400 (2) | 0.0250 (8) | |
C7 | 0.1972 (5) | 0.76244 (16) | 0.27073 (19) | 0.0224 (7) | |
C8 | 0.0761 (5) | 0.80838 (17) | 0.2278 (2) | 0.0252 (8) | |
H8 | 0.100244 | 0.824000 | 0.178708 | 0.030* | |
C9 | −0.0785 (5) | 0.83138 (17) | 0.25581 (19) | 0.0246 (8) | |
H9 | −0.158171 | 0.862687 | 0.225698 | 0.030* | |
C10 | −0.1198 (5) | 0.80931 (16) | 0.32791 (19) | 0.0228 (7) | |
C11 | 0.0037 (5) | 0.76200 (16) | 0.36992 (19) | 0.0231 (7) | |
H11 | −0.021132 | 0.745248 | 0.418341 | 0.028* | |
C12 | 0.1561 (5) | 0.74013 (16) | 0.34260 (19) | 0.0224 (7) | |
H12 | 0.236621 | 0.709094 | 0.372800 | 0.027* | |
C13 | −0.3920 (6) | 0.8812 (2) | 0.3115 (2) | 0.0335 (9) | |
H13A | −0.316164 | 0.917247 | 0.297878 | 0.050* | |
H13B | −0.480582 | 0.897404 | 0.343356 | 0.050* | |
H13C | −0.461935 | 0.861391 | 0.262779 | 0.050* | |
C14 | −0.3345 (5) | 0.79854 (19) | 0.4205 (2) | 0.0317 (9) | |
H14A | −0.362432 | 0.753380 | 0.404788 | 0.047* | |
H14B | −0.448483 | 0.819504 | 0.431022 | 0.047* | |
H14C | −0.236554 | 0.799703 | 0.468596 | 0.047* | |
C15 | 0.7514 (5) | 0.53281 (16) | 0.46159 (18) | 0.0197 (7) | |
C16 | 0.8187 (4) | 0.55641 (16) | 0.53831 (19) | 0.0179 (7) | |
C17 | 0.8149 (5) | 0.51475 (17) | 0.60199 (18) | 0.0202 (7) | |
C18 | 0.7471 (5) | 0.45259 (16) | 0.59164 (19) | 0.0211 (7) | |
C19 | 0.6811 (5) | 0.42983 (16) | 0.5161 (2) | 0.0217 (7) | |
C20 | 0.6825 (5) | 0.47031 (17) | 0.45225 (19) | 0.0218 (7) | |
C21 | 0.6473 (7) | 0.5202 (3) | 0.8395 (3) | 0.0568 (13) | |
H21 | 0.625020 | 0.540463 | 0.788953 | 0.068* | |
C22 | 0.7002 (7) | 0.5565 (2) | 0.9062 (3) | 0.0576 (13) | |
H22 | 0.711853 | 0.602217 | 0.902012 | 0.069* | |
C23 | 0.7371 (8) | 0.5272 (3) | 0.9801 (3) | 0.0645 (15) | |
H23 | 0.777702 | 0.552259 | 1.026559 | 0.077* | |
C24 | 0.7139 (7) | 0.4603 (2) | 0.9852 (3) | 0.0541 (13) | |
H24 | 0.736633 | 0.439528 | 1.035522 | 0.065* | |
C25 | 0.6582 (6) | 0.4247 (2) | 0.9176 (3) | 0.0418 (11) | |
H25 | 0.641769 | 0.379148 | 0.920935 | 0.050* | |
C26 | 0.6261 (6) | 0.4547 (2) | 0.8449 (3) | 0.0476 (12) | |
H26 | 0.588819 | 0.429650 | 0.798129 | 0.057* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.02514 (13) | 0.02112 (13) | 0.01538 (11) | 0.00266 (9) | 0.00210 (9) | 0.00049 (8) |
F1 | 0.0349 (12) | 0.0270 (11) | 0.0152 (9) | −0.0048 (9) | 0.0015 (8) | −0.0012 (8) |
N1 | 0.0290 (17) | 0.0240 (16) | 0.0196 (14) | 0.0011 (13) | 0.0012 (12) | 0.0012 (12) |
C1 | 0.033 (2) | 0.029 (2) | 0.0265 (19) | 0.0049 (16) | 0.0024 (16) | 0.0009 (15) |
I2 | 0.02672 (13) | 0.01681 (12) | 0.01653 (11) | −0.00109 (8) | 0.00324 (9) | −0.00140 (8) |
F2 | 0.0301 (12) | 0.0213 (11) | 0.0241 (10) | −0.0030 (8) | 0.0060 (9) | 0.0065 (8) |
N2 | 0.0330 (18) | 0.0234 (16) | 0.0190 (14) | 0.0023 (13) | 0.0007 (13) | 0.0018 (12) |
C2 | 0.032 (2) | 0.039 (2) | 0.0211 (18) | 0.0024 (17) | 0.0066 (15) | −0.0020 (16) |
F3 | 0.0300 (11) | 0.0177 (10) | 0.0335 (11) | −0.0030 (8) | 0.0048 (9) | −0.0023 (8) |
N3 | 0.0278 (17) | 0.0289 (17) | 0.0207 (15) | 0.0050 (13) | 0.0034 (13) | 0.0048 (12) |
C3 | 0.039 (2) | 0.031 (2) | 0.0201 (17) | −0.0005 (17) | 0.0064 (16) | 0.0030 (15) |
F4 | 0.0321 (12) | 0.0229 (11) | 0.0213 (10) | −0.0001 (9) | 0.0013 (8) | −0.0068 (8) |
C4 | 0.0276 (19) | 0.0195 (18) | 0.0189 (16) | 0.0011 (14) | 0.0025 (14) | −0.0007 (13) |
C5 | 0.033 (2) | 0.0197 (18) | 0.0197 (17) | −0.0009 (15) | 0.0026 (15) | 0.0031 (13) |
C6 | 0.037 (2) | 0.0165 (17) | 0.0201 (17) | −0.0008 (15) | 0.0010 (15) | 0.0022 (13) |
C7 | 0.028 (2) | 0.0168 (17) | 0.0213 (17) | −0.0026 (14) | 0.0037 (14) | −0.0008 (13) |
C8 | 0.032 (2) | 0.0241 (19) | 0.0190 (17) | −0.0012 (15) | 0.0037 (15) | 0.0020 (14) |
C9 | 0.034 (2) | 0.0204 (18) | 0.0191 (16) | 0.0054 (15) | 0.0045 (15) | 0.0043 (14) |
C10 | 0.0286 (19) | 0.0209 (18) | 0.0172 (16) | 0.0003 (14) | 0.0004 (14) | −0.0012 (13) |
C11 | 0.033 (2) | 0.0197 (18) | 0.0164 (15) | −0.0048 (15) | 0.0031 (14) | 0.0027 (13) |
C12 | 0.030 (2) | 0.0163 (17) | 0.0187 (16) | −0.0004 (14) | −0.0012 (14) | 0.0020 (13) |
C13 | 0.035 (2) | 0.036 (2) | 0.0281 (19) | 0.0105 (18) | 0.0032 (16) | 0.0036 (17) |
C14 | 0.034 (2) | 0.038 (2) | 0.0261 (19) | 0.0025 (17) | 0.0117 (16) | 0.0038 (16) |
C15 | 0.0195 (17) | 0.0238 (18) | 0.0155 (15) | 0.0015 (13) | 0.0028 (13) | 0.0014 (13) |
C16 | 0.0160 (16) | 0.0180 (16) | 0.0198 (16) | 0.0027 (13) | 0.0037 (13) | −0.0004 (13) |
C17 | 0.0205 (17) | 0.0256 (18) | 0.0137 (15) | 0.0033 (14) | 0.0014 (13) | −0.0010 (13) |
C18 | 0.0190 (17) | 0.0240 (18) | 0.0210 (16) | 0.0028 (14) | 0.0060 (14) | 0.0053 (13) |
C19 | 0.0214 (18) | 0.0165 (17) | 0.0285 (18) | 0.0009 (14) | 0.0081 (14) | −0.0009 (14) |
C20 | 0.0221 (18) | 0.0238 (18) | 0.0181 (16) | 0.0031 (14) | 0.0008 (13) | −0.0051 (13) |
C21 | 0.063 (3) | 0.049 (3) | 0.058 (3) | 0.007 (3) | 0.011 (3) | 0.018 (3) |
C22 | 0.056 (3) | 0.034 (3) | 0.084 (4) | 0.000 (2) | 0.019 (3) | 0.002 (3) |
C23 | 0.078 (4) | 0.048 (3) | 0.060 (3) | 0.004 (3) | −0.004 (3) | −0.021 (3) |
C24 | 0.073 (4) | 0.047 (3) | 0.038 (3) | 0.004 (2) | 0.001 (2) | 0.001 (2) |
C25 | 0.047 (3) | 0.034 (2) | 0.042 (2) | −0.0030 (19) | 0.001 (2) | 0.0020 (19) |
C26 | 0.051 (3) | 0.049 (3) | 0.039 (2) | −0.001 (2) | 0.000 (2) | −0.003 (2) |
Geometric parameters (Å, º) top
I1—C15 | 2.110 (3) | C11—C12 | 1.359 (5) |
F1—C17 | 1.347 (3) | C11—H11 | 0.9500 |
N1—C1 | 1.331 (5) | C12—H12 | 0.9500 |
N1—C4 | 1.347 (4) | C13—H13A | 0.9800 |
C1—C2 | 1.387 (5) | C13—H13B | 0.9800 |
C1—H1 | 0.9500 | C13—H13C | 0.9800 |
I2—C16 | 2.097 (3) | C14—H14A | 0.9800 |
F2—C18 | 1.340 (4) | C14—H14B | 0.9800 |
N2—C3 | 1.345 (5) | C14—H14C | 0.9800 |
N2—C4 | 1.354 (4) | C15—C20 | 1.380 (5) |
C2—C3 | 1.376 (5) | C15—C16 | 1.402 (4) |
C2—H2 | 0.9500 | C16—C17 | 1.396 (4) |
F3—C19 | 1.343 (4) | C17—C18 | 1.372 (5) |
N3—C10 | 1.365 (5) | C18—C19 | 1.376 (5) |
N3—C14 | 1.457 (4) | C19—C20 | 1.381 (5) |
N3—C13 | 1.459 (4) | C21—C22 | 1.361 (7) |
C3—H3 | 0.9500 | C21—C26 | 1.364 (7) |
F4—C20 | 1.349 (4) | C21—H21 | 0.9500 |
C4—C5 | 1.416 (5) | C22—C23 | 1.386 (7) |
C5—C6 | 1.205 (5) | C22—H22 | 0.9500 |
C6—C7 | 1.432 (5) | C23—C24 | 1.394 (7) |
C7—C8 | 1.401 (5) | C23—H23 | 0.9500 |
C7—C12 | 1.403 (5) | C24—C25 | 1.368 (6) |
C8—C9 | 1.387 (5) | C24—H24 | 0.9500 |
C8—H8 | 0.9500 | C25—C26 | 1.372 (6) |
C9—C10 | 1.406 (5) | C25—H25 | 0.9500 |
C9—H9 | 0.9500 | C26—H26 | 0.9500 |
C10—C11 | 1.423 (5) | | |
| | | |
C1—N1—C4 | 116.9 (3) | N3—C14—H14A | 109.5 |
N1—C1—C2 | 122.5 (3) | N3—C14—H14B | 109.5 |
N1—C1—H1 | 118.7 | H14A—C14—H14B | 109.5 |
C2—C1—H1 | 118.7 | N3—C14—H14C | 109.5 |
C3—N2—C4 | 115.7 (3) | H14A—C14—H14C | 109.5 |
C3—C2—C1 | 116.4 (4) | H14B—C14—H14C | 109.5 |
C3—C2—H2 | 121.8 | C20—C15—C16 | 119.1 (3) |
C1—C2—H2 | 121.8 | C20—C15—I1 | 118.3 (2) |
C10—N3—C14 | 119.9 (3) | C16—C15—I1 | 122.6 (2) |
C10—N3—C13 | 119.6 (3) | C17—C16—C15 | 117.9 (3) |
C14—N3—C13 | 118.6 (3) | C17—C16—I2 | 117.8 (2) |
N2—C3—C2 | 123.2 (3) | C15—C16—I2 | 124.3 (2) |
N2—C3—H3 | 118.4 | F1—C17—C18 | 117.4 (3) |
C2—C3—H3 | 118.4 | F1—C17—C16 | 120.3 (3) |
N1—C4—N2 | 125.2 (3) | C18—C17—C16 | 122.3 (3) |
N1—C4—C5 | 118.4 (3) | F2—C18—C17 | 120.0 (3) |
N2—C4—C5 | 116.3 (3) | F2—C18—C19 | 120.6 (3) |
C6—C5—C4 | 176.4 (4) | C17—C18—C19 | 119.4 (3) |
C5—C6—C7 | 177.6 (4) | F3—C19—C18 | 120.2 (3) |
C8—C7—C12 | 117.9 (3) | F3—C19—C20 | 120.5 (3) |
C8—C7—C6 | 120.0 (3) | C18—C19—C20 | 119.3 (3) |
C12—C7—C6 | 122.0 (3) | F4—C20—C15 | 120.8 (3) |
C9—C8—C7 | 120.9 (3) | F4—C20—C19 | 117.2 (3) |
C9—C8—H8 | 119.5 | C15—C20—C19 | 122.0 (3) |
C7—C8—H8 | 119.5 | C22—C21—C26 | 120.3 (5) |
C8—C9—C10 | 121.3 (3) | C22—C21—H21 | 119.8 |
C8—C9—H9 | 119.3 | C26—C21—H21 | 119.8 |
C10—C9—H9 | 119.3 | C21—C22—C23 | 120.3 (5) |
N3—C10—C9 | 121.7 (3) | C21—C22—H22 | 119.9 |
N3—C10—C11 | 121.6 (3) | C23—C22—H22 | 119.9 |
C9—C10—C11 | 116.7 (3) | C22—C23—C24 | 119.1 (5) |
C12—C11—C10 | 121.7 (3) | C22—C23—H23 | 120.4 |
C12—C11—H11 | 119.1 | C24—C23—H23 | 120.4 |
C10—C11—H11 | 119.1 | C25—C24—C23 | 119.7 (5) |
C11—C12—C7 | 121.4 (3) | C25—C24—H24 | 120.1 |
C11—C12—H12 | 119.3 | C23—C24—H24 | 120.1 |
C7—C12—H12 | 119.3 | C24—C25—C26 | 120.1 (4) |
N3—C13—H13A | 109.5 | C24—C25—H25 | 119.9 |
N3—C13—H13B | 109.5 | C26—C25—H25 | 119.9 |
H13A—C13—H13B | 109.5 | C21—C26—C25 | 120.4 (5) |
N3—C13—H13C | 109.5 | C21—C26—H26 | 119.8 |
H13A—C13—H13C | 109.5 | C25—C26—H26 | 119.8 |
H13B—C13—H13C | 109.5 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9···F4i | 0.95 | 2.57 | 3.296 (4) | 134 |
C11—H11···I2ii | 0.95 | 3.25 | 4.173 (3) | 163 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) x−1, 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·C6F4I2 | F(000) = 1184 |
Mr = 625.13 | Dx = 1.937 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.0191 (18) Å | Cell parameters from 9994 reflections |
b = 26.805 (5) Å | θ = 2.4–27.3° |
c = 9.5664 (19) Å | µ = 2.98 mm−1 |
β = 112.052 (3)° | T = 100 K |
V = 2143.6 (7) Å3 | Cut block, colourless |
Z = 4 | 0.33 × 0.32 × 0.12 mm |
Data collection top
Bruker APEXII CCD diffractometer | 4793 measured reflections |
Radiation source: fine-focus sealed tube | 26551 independent reflections |
Graphite monochromator | 4305 reflections with I > 2σ(I) |
Detector resolution: 8.3660 pixels mm-1 | θmax = 27.4°, θmin = 1.5° |
phi and ω scans | h = −11→11 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −34→34 |
Tmin = 0.393, Tmax = 0.691 | l = −10→12 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.056 | H-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 reflections | Δρmax = 3.63 e Å−3 |
265 parameters | Δρmin = −3.33 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. |
Refinement. Refined as a 2-component twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
I1 | 0.42385 (7) | 0.75016 (2) | 0.88434 (7) | 0.02056 (15) | |
F1 | 0.7099 (6) | 0.77369 (18) | 0.7652 (7) | 0.0251 (12) | |
N1 | 0.2630 (9) | 0.6585 (3) | 0.9476 (10) | 0.0226 (16) | |
C1 | 0.1539 (12) | 0.6603 (4) | 1.0098 (12) | 0.027 (2) | |
H1 | 0.125689 | 0.691956 | 1.037259 | 0.032* | |
I2 | 0.69015 (7) | 0.97266 (2) | 0.67044 (7) | 0.02209 (15) | |
F2 | 0.8057 (7) | 0.8576 (2) | 0.6788 (7) | 0.0266 (13) | |
N2 | 0.2295 (10) | 0.5695 (3) | 0.9308 (10) | 0.0239 (16) | |
C2 | 0.0791 (12) | 0.6182 (4) | 1.0366 (12) | 0.031 (2) | |
H2 | 0.002109 | 0.620416 | 1.082125 | 0.037* | |
F3 | 0.4304 (7) | 0.9485 (2) | 0.8144 (7) | 0.0305 (13) | |
N3 | 1.0120 (10) | 0.6228 (3) | 0.5699 (11) | 0.0278 (18) | |
C3 | 0.1217 (12) | 0.5730 (4) | 0.9941 (12) | 0.026 (2) | |
H3 | 0.072427 | 0.543452 | 1.010500 | 0.031* | |
F4 | 0.3284 (7) | 0.8645 (2) | 0.8935 (7) | 0.0289 (13) | |
C4 | 0.2983 (11) | 0.6123 (3) | 0.9113 (11) | 0.0199 (18) | |
C5 | 0.4176 (11) | 0.6097 (3) | 0.8469 (10) | 0.0195 (18) | |
C6 | 0.5212 (11) | 0.6081 (3) | 0.7975 (11) | 0.0208 (19) | |
C7 | 0.6456 (10) | 0.6104 (3) | 0.7397 (10) | 0.0181 (17) | |
C8 | 0.7068 (11) | 0.5678 (3) | 0.6941 (11) | 0.0226 (19) | |
H8 | 0.664173 | 0.535938 | 0.701265 | 0.027* | |
C9 | 0.8276 (11) | 0.5716 (3) | 0.6392 (12) | 0.0228 (19) | |
H9 | 0.867920 | 0.542107 | 0.611060 | 0.027* | |
C10 | 0.8929 (11) | 0.6185 (3) | 0.6239 (11) | 0.0213 (19) | |
C11 | 0.8282 (11) | 0.6613 (3) | 0.6672 (11) | 0.0227 (19) | |
H11 | 0.867659 | 0.693423 | 0.657046 | 0.027* | |
C12 | 0.7092 (11) | 0.6571 (3) | 0.7235 (11) | 0.0217 (19) | |
H12 | 0.668818 | 0.686418 | 0.752365 | 0.026* | |
C13 | 1.0778 (12) | 0.5792 (4) | 0.5224 (12) | 0.026 (2) | |
H13A | 1.119164 | 0.555705 | 0.606608 | 0.039* | |
H13B | 1.164843 | 0.589687 | 0.491152 | 0.039* | |
H13C | 0.993665 | 0.563070 | 0.437554 | 0.039* | |
C14 | 1.0742 (12) | 0.6715 (4) | 0.5514 (13) | 0.028 (2) | |
H14A | 0.989244 | 0.690834 | 0.476250 | 0.042* | |
H14B | 1.163318 | 0.667068 | 0.517538 | 0.042* | |
H14C | 1.111865 | 0.689204 | 0.648041 | 0.042* | |
C15 | 0.5138 (11) | 0.8161 (3) | 0.8288 (11) | 0.0199 (18) | |
C16 | 0.6361 (11) | 0.8168 (3) | 0.7749 (10) | 0.0187 (18) | |
C17 | 0.6883 (10) | 0.8604 (3) | 0.7332 (10) | 0.0174 (17) | |
C18 | 0.6211 (11) | 0.9060 (3) | 0.7417 (11) | 0.0208 (18) | |
C19 | 0.5022 (12) | 0.9056 (3) | 0.8000 (11) | 0.024 (2) | |
C20 | 0.4484 (11) | 0.8620 (3) | 0.8413 (10) | 0.0205 (18) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.0219 (3) | 0.0166 (3) | 0.0240 (3) | −0.0029 (2) | 0.0095 (2) | 0.0011 (2) |
F1 | 0.026 (3) | 0.012 (2) | 0.041 (3) | 0.002 (2) | 0.017 (3) | −0.001 (2) |
N1 | 0.023 (4) | 0.020 (4) | 0.025 (4) | 0.000 (3) | 0.009 (3) | −0.004 (3) |
C1 | 0.027 (5) | 0.027 (5) | 0.030 (5) | 0.005 (4) | 0.014 (4) | −0.004 (4) |
I2 | 0.0227 (3) | 0.0142 (3) | 0.0275 (3) | −0.0015 (2) | 0.0074 (3) | 0.0033 (2) |
F2 | 0.023 (3) | 0.022 (3) | 0.041 (4) | −0.001 (2) | 0.020 (3) | 0.001 (2) |
N2 | 0.026 (4) | 0.021 (4) | 0.029 (4) | −0.001 (3) | 0.016 (4) | 0.000 (3) |
C2 | 0.025 (5) | 0.044 (6) | 0.028 (6) | 0.001 (4) | 0.016 (5) | −0.003 (5) |
F3 | 0.035 (3) | 0.016 (3) | 0.045 (4) | 0.006 (2) | 0.021 (3) | 0.001 (3) |
N3 | 0.029 (4) | 0.018 (4) | 0.046 (5) | −0.005 (3) | 0.024 (4) | 0.001 (4) |
C3 | 0.024 (5) | 0.020 (4) | 0.033 (5) | −0.004 (4) | 0.010 (4) | 0.005 (4) |
F4 | 0.032 (3) | 0.023 (3) | 0.040 (3) | 0.003 (2) | 0.022 (3) | 0.000 (3) |
C4 | 0.022 (4) | 0.015 (4) | 0.026 (5) | 0.001 (3) | 0.013 (4) | 0.001 (4) |
C5 | 0.019 (4) | 0.017 (4) | 0.021 (4) | 0.001 (3) | 0.006 (4) | 0.001 (3) |
C6 | 0.021 (4) | 0.014 (4) | 0.025 (5) | 0.001 (3) | 0.006 (4) | 0.000 (3) |
C7 | 0.013 (4) | 0.024 (4) | 0.017 (4) | 0.002 (3) | 0.005 (3) | 0.003 (4) |
C8 | 0.019 (4) | 0.022 (4) | 0.026 (5) | −0.003 (3) | 0.009 (4) | −0.002 (4) |
C9 | 0.025 (5) | 0.016 (4) | 0.034 (5) | −0.004 (3) | 0.019 (4) | −0.002 (4) |
C10 | 0.020 (4) | 0.019 (4) | 0.025 (5) | −0.001 (3) | 0.009 (4) | 0.004 (4) |
C11 | 0.023 (4) | 0.015 (4) | 0.031 (5) | 0.001 (3) | 0.010 (4) | 0.004 (4) |
C12 | 0.018 (4) | 0.020 (4) | 0.027 (5) | 0.004 (3) | 0.009 (4) | 0.003 (4) |
C13 | 0.023 (5) | 0.027 (5) | 0.029 (5) | 0.001 (4) | 0.011 (4) | −0.003 (4) |
C14 | 0.027 (5) | 0.021 (5) | 0.044 (6) | −0.003 (4) | 0.022 (5) | 0.004 (4) |
C15 | 0.026 (4) | 0.014 (4) | 0.020 (4) | −0.003 (3) | 0.009 (4) | −0.001 (3) |
C16 | 0.019 (4) | 0.009 (4) | 0.024 (5) | −0.001 (3) | 0.004 (4) | −0.003 (3) |
C17 | 0.019 (4) | 0.016 (4) | 0.018 (4) | −0.002 (3) | 0.008 (4) | 0.000 (3) |
C18 | 0.023 (4) | 0.015 (4) | 0.022 (5) | −0.003 (3) | 0.006 (4) | −0.001 (3) |
C19 | 0.029 (5) | 0.017 (4) | 0.022 (5) | 0.002 (4) | 0.006 (4) | −0.003 (4) |
C20 | 0.020 (4) | 0.022 (4) | 0.023 (4) | 0.000 (4) | 0.012 (4) | −0.001 (4) |
Geometric parameters (Å, º) top
I1—C15 | 2.096 (9) | C7—C12 | 1.410 (12) |
F1—C16 | 1.355 (10) | C8—C9 | 1.379 (13) |
N1—C1 | 1.329 (13) | C8—H8 | 0.9500 |
N1—C4 | 1.357 (11) | C9—C10 | 1.419 (12) |
C1—C2 | 1.387 (15) | C9—H9 | 0.9500 |
C1—H1 | 0.9500 | C10—C11 | 1.419 (13) |
I2—C18 | 2.090 (9) | C11—C12 | 1.374 (13) |
F2—C17 | 1.346 (10) | C11—H11 | 0.9500 |
N2—C3 | 1.328 (13) | C12—H12 | 0.9500 |
N2—C4 | 1.348 (11) | C13—H13A | 0.9800 |
C2—C3 | 1.377 (14) | C13—H13B | 0.9800 |
C2—H2 | 0.9500 | C13—H13C | 0.9800 |
F3—C19 | 1.353 (10) | C14—H14A | 0.9800 |
N3—C10 | 1.360 (12) | C14—H14B | 0.9800 |
N3—C13 | 1.456 (12) | C14—H14C | 0.9800 |
N3—C14 | 1.458 (12) | C15—C16 | 1.382 (13) |
C3—H3 | 0.9500 | C15—C20 | 1.386 (12) |
F4—C20 | 1.353 (10) | C16—C17 | 1.375 (12) |
C4—C5 | 1.428 (13) | C17—C18 | 1.378 (12) |
C5—C6 | 1.196 (13) | C18—C19 | 1.382 (14) |
C6—C7 | 1.427 (13) | C19—C20 | 1.379 (13) |
C7—C8 | 1.406 (13) | | |
| | | |
C1—N1—C4 | 115.6 (8) | C11—C12—C7 | 121.8 (9) |
N1—C1—C2 | 123.1 (9) | C11—C12—H12 | 119.1 |
N1—C1—H1 | 118.5 | C7—C12—H12 | 119.1 |
C2—C1—H1 | 118.5 | N3—C13—H13A | 109.5 |
C3—N2—C4 | 117.2 (8) | N3—C13—H13B | 109.5 |
C3—C2—C1 | 116.9 (9) | H13A—C13—H13B | 109.5 |
C3—C2—H2 | 121.6 | N3—C13—H13C | 109.5 |
C1—C2—H2 | 121.6 | H13A—C13—H13C | 109.5 |
C10—N3—C13 | 121.5 (8) | H13B—C13—H13C | 109.5 |
C10—N3—C14 | 121.1 (8) | N3—C14—H14A | 109.5 |
C13—N3—C14 | 117.3 (8) | N3—C14—H14B | 109.5 |
N2—C3—C2 | 122.0 (9) | H14A—C14—H14B | 109.5 |
N2—C3—H3 | 119.0 | N3—C14—H14C | 109.5 |
C2—C3—H3 | 119.0 | H14A—C14—H14C | 109.5 |
N2—C4—N1 | 125.2 (8) | H14B—C14—H14C | 109.5 |
N2—C4—C5 | 118.6 (8) | C16—C15—C20 | 116.4 (8) |
N1—C4—C5 | 116.2 (8) | C16—C15—I1 | 123.0 (6) |
C6—C5—C4 | 177.8 (10) | C20—C15—I1 | 120.5 (7) |
C5—C6—C7 | 175.4 (10) | F1—C16—C17 | 118.3 (8) |
C8—C7—C12 | 117.6 (8) | F1—C16—C15 | 119.8 (8) |
C8—C7—C6 | 122.8 (8) | C17—C16—C15 | 121.9 (8) |
C12—C7—C6 | 119.5 (8) | F2—C17—C16 | 118.0 (8) |
C9—C8—C7 | 121.1 (9) | F2—C17—C18 | 120.0 (8) |
C9—C8—H8 | 119.4 | C16—C17—C18 | 122.0 (8) |
C7—C8—H8 | 119.4 | C17—C18—C19 | 116.3 (8) |
C8—C9—C10 | 121.5 (9) | C17—C18—I2 | 123.1 (7) |
C8—C9—H9 | 119.3 | C19—C18—I2 | 120.6 (7) |
C10—C9—H9 | 119.3 | F3—C19—C20 | 117.3 (9) |
N3—C10—C11 | 120.8 (8) | F3—C19—C18 | 120.5 (8) |
N3—C10—C9 | 122.1 (9) | C20—C19—C18 | 122.1 (9) |
C11—C10—C9 | 117.0 (8) | F4—C20—C19 | 118.6 (8) |
C12—C11—C10 | 121.0 (8) | F4—C20—C15 | 120.1 (8) |
C12—C11—H11 | 119.5 | C19—C20—C15 | 121.3 (8) |
C10—C11—H11 | 119.5 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···F2i | 0.95 | 2.36 | 3.297 (12) | 169 |
C13—H13A···I2ii | 0.98 | 3.12 | 4.069 (10) | 165 |
C13—H13B···F4iii | 0.98 | 2.36 | 3.316 (12) | 164 |
C13—H13C···I2iv | 0.98 | 3.11 | 4.081 (10) | 170 |
C14—H14B···F4iii | 0.98 | 2.38 | 3.327 (12) | 162 |
C14—H14C···I1v | 0.98 | 3.30 | 4.123 (11) | 142 |
Symmetry codes: (i) x−1, −y+3/2, z+1/2; (ii) −x+2, y−1/2, −z+3/2; (iii) x+1, −y+3/2, z−1/2; (iv) x, −y+3/2, z−1/2; (v) x+1, y, z. |
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