Ditopic halogen bonding with bi­pyrimidines and activated pyrimidines

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.

Computing details

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)

Crystal data

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) Å^3	Cut, colourless
Z = 8	0.2 × 0.1 × 0.03 mm

Data collection

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

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.020	H-atom parameters constrained
wR(F^2) = 0.050	w = 1/[σ^2(Fo^2) + (0.0273P)^2 + 4.1245P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N2^i	0.95	2.53	3.473 (3)	175
C2—H2···F4^ii	0.95	2.60	3.370 (3)	138
C8—H8···N4^ii	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)

Crystal data

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) Å^3	Cut, colourless
Z = 4	0.44 × 0.23 × 0.09 mm

Data collection

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

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.029	H-atom parameters constrained
wR(F^2) = 0.051	w = 1/[σ^2(Fo^2) + (0.0041P)^2 + 4.730P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···I1^i	0.95	3.28	4.020 (4)	137
C7—H7···F2^ii	0.95	2.57	3.424 (4)	150
C8—H8···N2^iii	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)

Crystal data

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) Å^3	Cut BLOCK, colourless
Z = 2	0.25 × 0.20 × 0.10 mm

Data collection

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

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.018	H-atom parameters constrained
wR(F^2) = 0.043	w = 1/[σ^2(Fo^2) + (0.0209P)^2 + 1.2801P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

I1—C12	2.0932 (18)	C5—C6	1.436 (4)
F1—C11	1.357 (3)	C6—C7^i	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—C10^i	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—C12^ii	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
N1^i—C1—N1	126.4 (3)	N2—C9—C8^i	121.18 (13)
N1^i—C1—H1	116.8	N2—C9—C8	121.18 (13)
N1—C1—H1	116.8	C8^i—C9—C8	117.6 (3)
C9—N2—C10^i	118.53 (13)	N2—C10—H10A	109.5
C9—N2—C10	118.53 (13)	N2—C10—H10B	109.5
C10^i—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—C2^i	115.8 (2)	F1—C11—C12^ii	118.21 (12)
C2—C3—C4	122.11 (12)	F1—C11—C12	118.21 (12)
C2^i—C3—C4	122.11 (12)	C12^ii—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)
C7^i—C6—C7	118.1 (3)	C13—C12—I1	120.47 (14)
C7^i—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—C13^ii	120.45 (12)
C7—C8—C9	120.9 (2)	C13—C14—C13^ii	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)

Crystal data

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) Å^3	0.50 × 0.27 × 0.17 mm

Data collection

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

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.021	H-atom parameters constrained
wR(F^2) = 0.050	w = 1/[σ^2(Fo^2) + (0.0241P)^2 + 0.6867P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···F8^i	0.95	2.57	3.170 (3)	121
C3—H3···F8^i	0.95	2.56	3.185 (3)	124
C13—H13A···I4^ii	0.98	3.18	3.828 (3)	125
C13—H13C···F5^iii	0.98	2.61	3.280 (3)	126
C14—H14B···F3^iv	0.98	2.46	3.391 (3)	158
C29—H29···F2^iv	0.95	2.47	3.145 (3)	128
C39—H39A···I3^v	0.98	3.22	4.187 (3)	170
C39—H39B···F7^vi	0.98	2.28	3.221 (3)	161
C39—H39C···I2^vii	0.98	3.27	4.117 (3)	146
C40—H40A···I4^viii	0.98	3.24	4.146 (3)	154
C40—H40C···I4^v	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)

Crystal data

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) Å^3	0.38 × 0.18 × 0.10 mm

Data collection

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

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.020	H-atom parameters constrained
wR(F^2) = 0.046	w = 1/[σ^2(Fo^2) + (0.0193P)^2 + 1.2644P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···F2^i	0.95	2.63	3.220 (3)	121
C14—H14B···F1^ii	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)

Crystal data

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) Å^3	Cut block, colourless
Z = 4	0.40 × 0.25 × 0.04 mm

Data collection

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

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.032	H-atom parameters constrained
wR(F^2) = 0.078	w = 1/[σ^2(Fo^2) + (0.0447P)^2] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···F4^i	0.95	2.57	3.296 (4)	134
C11—H11···I2^ii	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)

Crystal data

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) Å^3	Cut block, colourless
Z = 4	0.33 × 0.32 × 0.12 mm

Data collection

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

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.056	H-atom parameters constrained
wR(F^2) = 0.147	w = 1/[σ^2(Fo^2) + 36.0237P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···F2^i	0.95	2.36	3.297 (12)	169
C13—H13A···I2^ii	0.98	3.12	4.069 (10)	165
C13—H13B···F4^iii	0.98	2.36	3.316 (12)	164
C13—H13C···I2^iv	0.98	3.11	4.081 (10)	170
C14—H14B···F4^iii	0.98	2.38	3.327 (12)	162
C14—H14C···I1^v	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.