Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S205322962400771X/vp3039sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S205322962400771X/vp30392DMAP.DITCBsup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S205322962400771X/vp30392DMAP.DITBBsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S205322962400771X/vp30392DMAP.IBTFBsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S205322962400771X/vp30392DMAP.DIBFBsup5.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S205322962400771X/vp30392DMAP.DITCBsup6.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S205322962400771X/vp30392DMAP.DITBBsup7.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S205322962400771X/vp30392DMAP.IBTFBsup8.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S205322962400771X/vp30392DMAP.DIBFBsup9.cml |
CCDC references: 2375541; 2375540; 2375539; 2375538
2C7H10N2·C6Cl4I2 | Z = 1 |
Mr = 712.03 | F(000) = 344.569 |
Triclinic, P1 | Dx = 1.987 Mg m−3 |
a = 8.1680 (3) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 9.1290 (4) Å | Cell parameters from 5533 reflections |
c = 9.8118 (3) Å | θ = 5.2–76.7° |
α = 103.727 (3)° | µ = 25.03 mm−1 |
β = 107.165 (3)° | T = 100 K |
γ = 112.180 (4)° | Block, colourless |
V = 594.91 (5) Å3 | 0.14 × 0.1 × 0.03 mm |
Rigaku XtaLAB Synergy Dualflex diffractometer with a HyPix detector | 2500 independent reflections |
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source | 2413 reflections with I ≥ 2u(I) |
Mirror monochromator | Rint = 0.063 |
Detector resolution: 10.0000 pixels mm-1 | θmax = 77.8°, θmin = 5.1° |
ω scans | h = −8→10 |
Absorption correction: analytical (CrysAlis PRO; Rigaku OD, 2023) | k = −11→11 |
Tmin = 0.104, Tmax = 0.510 | l = −12→10 |
8921 measured reflections |
Refinement on F2 | 16 constraints |
Least-squares matrix: full | Primary atom site location: dual |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.107 | w = 1/[σ2(Fo2) + (0.0833P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = −0.0004 |
2500 reflections | Δρmax = 1.33 e Å−3 |
138 parameters | Δρmin = −1.51 e Å−3 |
0 restraints |
x | y | z | Uiso*/Ueq | ||
I1 | 0.66832 (3) | 0.55170 (3) | 0.83016 (2) | 0.02027 (14) | |
Cl1 | 0.55433 (14) | 0.87164 (13) | 0.82188 (12) | 0.0244 (2) | |
Cl2 | 0.84204 (14) | 1.25822 (12) | 0.96798 (12) | 0.0236 (2) | |
N1 | 0.4176 (6) | 0.2104 (5) | 0.6920 (5) | 0.0256 (8) | |
N2 | −0.0264 (6) | −0.3045 (5) | 0.4505 (5) | 0.0265 (8) | |
C10 | 0.9318 (6) | 1.1168 (5) | 0.9868 (5) | 0.0191 (7) | |
C2 | 0.3727 (6) | 0.1184 (6) | 0.5449 (5) | 0.0250 (8) | |
H2 | 0.4439 (6) | 0.1742 (6) | 0.4948 (5) | 0.0299 (10)* | |
C5 | 0.1183 (6) | −0.1363 (5) | 0.5291 (5) | 0.0206 (8) | |
C9 | 0.8010 (6) | 0.9401 (5) | 0.9196 (5) | 0.0197 (7) | |
C1 | 0.2313 (6) | −0.0503 (6) | 0.4621 (5) | 0.0246 (8) | |
H1 | 0.2100 (6) | −0.1089 (6) | 0.3594 (5) | 0.0295 (10)* | |
C3 | 0.3125 (6) | 0.1261 (5) | 0.7584 (5) | 0.0240 (8) | |
H3 | 0.3424 (6) | 0.1869 (5) | 0.8631 (5) | 0.0287 (10)* | |
C8 | 0.8668 (6) | 0.8202 (5) | 0.9319 (5) | 0.0197 (8) | |
C4 | 0.1660 (6) | −0.0410 (6) | 0.6849 (5) | 0.0233 (8) | |
H4 | 0.0967 (6) | −0.0928 (6) | 0.7379 (5) | 0.0280 (10)* | |
C6 | −0.1438 (7) | −0.3878 (6) | 0.5229 (6) | 0.0297 (9) | |
H6a | −0.0579 (8) | −0.381 (4) | 0.621 (2) | 0.0445 (14)* | |
H6b | −0.218 (4) | −0.330 (3) | 0.544 (4) | 0.0445 (14)* | |
H6c | −0.234 (4) | −0.5088 (14) | 0.453 (2) | 0.0445 (14)* | |
C7 | −0.0832 (7) | −0.3915 (6) | 0.2866 (5) | 0.0287 (9) | |
H7a | −0.119 (5) | −0.325 (3) | 0.2303 (8) | 0.0431 (13)* | |
H7b | 0.027 (2) | −0.402 (4) | 0.2728 (6) | 0.0431 (13)* | |
H7c | −0.195 (4) | −0.5064 (19) | 0.2461 (12) | 0.0431 (13)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.01750 (18) | 0.01770 (19) | 0.02180 (19) | 0.00611 (13) | 0.00822 (13) | 0.00595 (13) |
Cl1 | 0.0153 (4) | 0.0225 (5) | 0.0289 (5) | 0.0072 (4) | 0.0055 (4) | 0.0081 (4) |
Cl2 | 0.0205 (5) | 0.0205 (5) | 0.0285 (5) | 0.0109 (4) | 0.0086 (4) | 0.0084 (4) |
N1 | 0.0211 (18) | 0.0238 (18) | 0.0272 (19) | 0.0105 (15) | 0.0079 (15) | 0.0063 (16) |
N2 | 0.0226 (18) | 0.0239 (18) | 0.0230 (18) | 0.0053 (15) | 0.0093 (15) | 0.0040 (15) |
C10 | 0.0201 (19) | 0.0204 (18) | 0.0195 (18) | 0.0102 (16) | 0.0113 (16) | 0.0082 (15) |
C2 | 0.021 (2) | 0.029 (2) | 0.029 (2) | 0.0129 (18) | 0.0130 (18) | 0.0147 (18) |
C5 | 0.0157 (19) | 0.0203 (19) | 0.024 (2) | 0.0101 (16) | 0.0052 (16) | 0.0067 (16) |
C9 | 0.0153 (17) | 0.0236 (19) | 0.0149 (18) | 0.0065 (15) | 0.0051 (14) | 0.0054 (15) |
C1 | 0.022 (2) | 0.025 (2) | 0.025 (2) | 0.0124 (17) | 0.0097 (17) | 0.0058 (17) |
C3 | 0.0191 (19) | 0.023 (2) | 0.026 (2) | 0.0087 (17) | 0.0091 (17) | 0.0068 (17) |
C8 | 0.0178 (19) | 0.0172 (18) | 0.021 (2) | 0.0058 (16) | 0.0089 (16) | 0.0066 (16) |
C4 | 0.0199 (19) | 0.026 (2) | 0.024 (2) | 0.0120 (17) | 0.0096 (17) | 0.0097 (17) |
C6 | 0.027 (2) | 0.027 (2) | 0.032 (2) | 0.0087 (19) | 0.013 (2) | 0.014 (2) |
C7 | 0.025 (2) | 0.021 (2) | 0.025 (2) | 0.0063 (17) | 0.0052 (18) | 0.0006 (17) |
I1—C8 | 2.125 (4) | C5—C4 | 1.417 (6) |
Cl1—C9 | 1.730 (4) | C9—C8 | 1.405 (6) |
Cl2—C10 | 1.728 (4) | C1—H1 | 0.9500 |
N1—C2 | 1.343 (6) | C3—H3 | 0.9500 |
N1—C3 | 1.350 (6) | C3—C4 | 1.367 (6) |
N2—C5 | 1.371 (6) | C4—H4 | 0.9500 |
N2—C6 | 1.453 (6) | C6—H6a | 0.9800 |
N2—C7 | 1.451 (6) | C6—H6b | 0.9800 |
C10—C9 | 1.398 (6) | C6—H6c | 0.9800 |
C10—C8i | 1.402 (6) | C7—H7a | 0.9800 |
C2—H2 | 0.9500 | C7—H7b | 0.9800 |
C2—C1 | 1.370 (6) | C7—H7c | 0.9800 |
C5—C1 | 1.398 (6) | ||
C3—N1—C2 | 115.7 (4) | C4—C3—N1 | 124.3 (4) |
C6—N2—C5 | 120.4 (4) | C4—C3—H3 | 117.8 (3) |
C7—N2—C5 | 119.7 (4) | C10i—C8—I1 | 121.0 (3) |
C7—N2—C6 | 119.2 (4) | C9—C8—I1 | 121.2 (3) |
C9—C10—Cl2 | 119.0 (3) | C9—C8—C10i | 117.8 (4) |
C8i—C10—Cl2 | 119.9 (3) | C3—C4—C5 | 119.5 (4) |
C8i—C10—C9 | 121.1 (4) | H4—C4—C5 | 120.3 (2) |
H2—C2—N1 | 117.8 (2) | H4—C4—C3 | 120.3 (3) |
C1—C2—N1 | 124.4 (4) | H6a—C6—N2 | 109.5 |
C1—C2—H2 | 117.8 (3) | H6b—C6—N2 | 109.5 |
C1—C5—N2 | 122.1 (4) | H6b—C6—H6a | 109.5 |
C4—C5—N2 | 121.8 (4) | H6c—C6—N2 | 109.5 |
C4—C5—C1 | 116.1 (4) | H6c—C6—H6a | 109.5 |
C10—C9—Cl1 | 118.5 (3) | H6c—C6—H6b | 109.5 |
C8—C9—Cl1 | 120.4 (3) | H7a—C7—N2 | 109.5 |
C8—C9—C10 | 121.1 (4) | H7b—C7—N2 | 109.5 |
C5—C1—C2 | 119.9 (4) | H7b—C7—H7a | 109.5 |
H1—C1—C2 | 120.1 (3) | H7c—C7—N2 | 109.5 |
H1—C1—C5 | 120.1 (2) | H7c—C7—H7a | 109.5 |
H3—C3—N1 | 117.8 (3) | H7c—C7—H7b | 109.5 |
I1—C8—C10i—Cl2i | −0.2 (3) | Cl2—C10—C8i—C9i | 179.9 (3) |
I1—C8—C10i—C9i | −179.9 (3) | N1—C2—C1—C5 | 2.1 (5) |
I1—C8—C9—Cl1 | 0.6 (3) | N1—C3—C4—C5 | 0.5 (5) |
I1—C8—C9—C10 | 179.9 (3) | N2—C5—C1—C2 | 179.3 (4) |
Cl1—C9—C10—Cl2 | −0.6 (3) | N2—C5—C4—C3 | 179.5 (4) |
Cl1—C9—C10—C8i | 179.7 (3) | C10—C9—C8—C10i | −0.4 (4) |
Cl1—C9—C8—C10i | −179.7 (3) | C10i—C8—C9—C10 | −0.4 (4) |
Cl2—C10—C9—C8 | −179.9 (3) | C2—C1—C5—C4 | −2.6 (5) |
Symmetry code: (i) −x+2, −y+2, −z+2. |
2C7H10N2·C6Br4I2 | Z = 1 |
Mr = 889.83 | F(000) = 412.446 |
Triclinic, P1 | Dx = 2.411 Mg m−3 |
a = 8.3361 (2) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 9.3089 (3) Å | Cell parameters from 8887 reflections |
c = 9.8204 (2) Å | θ = 5.1–76.2° |
α = 102.484 (2)° | µ = 27.92 mm−1 |
β = 108.399 (2)° | T = 100 K |
γ = 113.064 (2)° | Irregular, clear colourless |
V = 612.84 (4) Å3 | 0.21 × 0.17 × 0.08 mm |
Rigaku XtaLAB Synergy Dualflex diffractometer with a HyPix detector | 2446 independent reflections |
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source | 2429 reflections with I ≥ 2u(I) |
Mirror monochromator | Rint = 0.055 |
Detector resolution: 10.0000 pixels mm-1 | θmax = 77.1°, θmin = 5.2° |
ω scans | h = −10→10 |
Absorption correction: analytical (CrysAlis PRO; Rigaku OD, 2023) | k = −8→11 |
Tmin = 0.011, Tmax = 0.146 | l = −12→11 |
11315 measured reflections |
Refinement on F2 | 16 constraints |
Least-squares matrix: full | Primary atom site location: dual |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.110 | w = 1/[σ2(Fo2) + (0.0862P)2 + 0.8994P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
2446 reflections | Δρmax = 1.81 e Å−3 |
138 parameters | Δρmin = −1.59 e Å−3 |
0 restraints |
x | y | z | Uiso*/Ueq | ||
I1 | 0.66402 (4) | 0.55739 (3) | 0.82970 (3) | 0.02993 (15) | |
Br1 | 1.15967 (7) | 0.73203 (6) | 1.03222 (6) | 0.03016 (17) | |
Br2 | 1.46760 (7) | 1.13485 (6) | 1.18536 (6) | 0.03136 (17) | |
N1 | 0.4123 (7) | 0.2193 (6) | 0.6942 (6) | 0.0353 (10) | |
N2 | −0.0154 (7) | −0.2952 (6) | 0.4640 (6) | 0.0353 (10) | |
C9 | 1.0645 (7) | 0.8856 (6) | 1.0133 (6) | 0.0272 (9) | |
C10 | 1.1981 (7) | 1.0596 (6) | 1.0791 (6) | 0.0275 (9) | |
C3 | 0.1231 (7) | −0.1283 (6) | 0.5382 (6) | 0.0288 (10) | |
C8 | 0.8650 (7) | 0.8220 (6) | 0.9320 (6) | 0.0276 (10) | |
C2 | 0.1625 (8) | −0.0294 (7) | 0.6879 (6) | 0.0326 (10) | |
H2 | 0.0909 (8) | −0.0788 (7) | 0.7395 (6) | 0.0391 (12)* | |
C4 | 0.2372 (8) | −0.0440 (7) | 0.4711 (6) | 0.0331 (10) | |
H4 | 0.2183 (8) | −0.1031 (7) | 0.3705 (6) | 0.0398 (12)* | |
C5 | 0.3767 (8) | 0.1251 (7) | 0.5530 (6) | 0.0318 (10) | |
H5 | 0.4529 (8) | 0.1783 (7) | 0.5058 (6) | 0.0381 (12)* | |
C1 | 0.3051 (8) | 0.1395 (6) | 0.7594 (6) | 0.0313 (10) | |
H1 | 0.3289 (8) | 0.2028 (6) | 0.8605 (6) | 0.0375 (12)* | |
C6 | −0.1347 (9) | −0.3752 (7) | 0.5351 (7) | 0.0389 (12) | |
H6a | −0.0505 (9) | −0.362 (6) | 0.638 (3) | 0.0583 (18)* | |
H6b | −0.213 (6) | −0.322 (4) | 0.546 (6) | 0.0583 (18)* | |
H6c | −0.221 (5) | −0.4962 (15) | 0.469 (3) | 0.0583 (18)* | |
C7 | −0.0661 (9) | −0.3860 (7) | 0.3027 (7) | 0.0415 (13) | |
H7a | −0.103 (7) | −0.326 (4) | 0.2392 (13) | 0.0623 (19)* | |
H7b | 0.046 (3) | −0.392 (6) | 0.2968 (11) | 0.0623 (19)* | |
H7c | −0.175 (5) | −0.501 (2) | 0.264 (2) | 0.0623 (19)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.0289 (2) | 0.0298 (2) | 0.0321 (2) | 0.01458 (16) | 0.01462 (16) | 0.01236 (15) |
Br1 | 0.0299 (3) | 0.0301 (3) | 0.0361 (3) | 0.0184 (2) | 0.0154 (2) | 0.0147 (2) |
Br2 | 0.0245 (3) | 0.0328 (3) | 0.0362 (3) | 0.0150 (2) | 0.0118 (2) | 0.0135 (2) |
N1 | 0.032 (2) | 0.034 (2) | 0.035 (2) | 0.0144 (19) | 0.0144 (19) | 0.0111 (19) |
N2 | 0.036 (2) | 0.037 (2) | 0.032 (2) | 0.016 (2) | 0.018 (2) | 0.0133 (19) |
C9 | 0.029 (2) | 0.031 (2) | 0.029 (2) | 0.0178 (19) | 0.016 (2) | 0.0135 (18) |
C10 | 0.025 (2) | 0.031 (2) | 0.028 (2) | 0.0134 (18) | 0.0143 (19) | 0.0132 (18) |
C3 | 0.026 (2) | 0.030 (2) | 0.031 (2) | 0.0150 (19) | 0.012 (2) | 0.0119 (19) |
C8 | 0.031 (2) | 0.028 (2) | 0.025 (2) | 0.0141 (19) | 0.014 (2) | 0.0108 (18) |
C2 | 0.029 (2) | 0.040 (3) | 0.035 (3) | 0.020 (2) | 0.016 (2) | 0.018 (2) |
C4 | 0.031 (2) | 0.041 (3) | 0.032 (2) | 0.020 (2) | 0.015 (2) | 0.015 (2) |
C5 | 0.031 (2) | 0.036 (2) | 0.037 (3) | 0.019 (2) | 0.020 (2) | 0.019 (2) |
C1 | 0.033 (3) | 0.031 (2) | 0.032 (2) | 0.017 (2) | 0.016 (2) | 0.011 (2) |
C6 | 0.034 (3) | 0.037 (3) | 0.039 (3) | 0.013 (2) | 0.014 (2) | 0.015 (2) |
C7 | 0.042 (3) | 0.034 (3) | 0.038 (3) | 0.014 (2) | 0.017 (3) | 0.006 (2) |
I1—C8 | 2.126 (5) | C2—H2 | 0.9500 |
Br1—C9 | 1.902 (5) | C2—C1 | 1.382 (8) |
Br2—C10 | 1.897 (5) | C4—H4 | 0.9500 |
N1—C5 | 1.338 (7) | C4—C5 | 1.380 (8) |
N1—C1 | 1.345 (7) | C5—H5 | 0.9500 |
N2—C3 | 1.361 (7) | C1—H1 | 0.9500 |
N2—C6 | 1.454 (8) | C6—H6a | 0.9800 |
N2—C7 | 1.457 (7) | C6—H6b | 0.9800 |
C9—C10 | 1.400 (7) | C6—H6c | 0.9800 |
C9—C8 | 1.393 (7) | C7—H7a | 0.9800 |
C10—C8i | 1.404 (7) | C7—H7b | 0.9800 |
C3—C2 | 1.411 (8) | C7—H7c | 0.9800 |
C3—C4 | 1.410 (7) | ||
C1—N1—C5 | 116.3 (5) | C5—C4—C3 | 119.4 (5) |
C6—N2—C3 | 120.3 (5) | C5—C4—H4 | 120.3 (3) |
C7—N2—C3 | 119.5 (5) | C4—C5—N1 | 124.6 (5) |
C7—N2—C6 | 119.4 (5) | H5—C5—N1 | 117.7 (3) |
C10—C9—Br1 | 118.8 (4) | H5—C5—C4 | 117.7 (3) |
C8—C9—Br1 | 119.3 (4) | C2—C1—N1 | 123.7 (5) |
C8—C9—C10 | 121.9 (5) | H1—C1—N1 | 118.1 (3) |
C9—C10—Br2 | 119.1 (4) | H1—C1—C2 | 118.1 (3) |
C8i—C10—Br2 | 120.0 (4) | H6a—C6—N2 | 109.5 |
C8i—C10—C9 | 121.0 (5) | H6b—C6—N2 | 109.5 |
C2—C3—N2 | 121.9 (5) | H6b—C6—H6a | 109.5 |
C4—C3—N2 | 122.2 (5) | H6c—C6—N2 | 109.5 |
C4—C3—C2 | 115.9 (5) | H6c—C6—H6a | 109.5 |
C9—C8—I1 | 121.5 (4) | H6c—C6—H6b | 109.5 |
C10i—C8—I1 | 121.3 (4) | H7a—C7—N2 | 109.5 |
C10i—C8—C9 | 117.1 (5) | H7b—C7—N2 | 109.5 |
H2—C2—C3 | 120.0 (3) | H7b—C7—H7a | 109.5 |
C1—C2—C3 | 120.1 (5) | H7c—C7—N2 | 109.5 |
C1—C2—H2 | 120.0 (3) | H7c—C7—H7a | 109.5 |
H4—C4—C3 | 120.3 (3) | H7c—C7—H7b | 109.5 |
I1—C8—C9—Br1 | 0.3 (4) | Br2—C10—C8i—C9i | 179.2 (4) |
I1—C8—C9—C10 | 179.1 (4) | N1—C5—C4—C3 | −0.9 (7) |
I1—C8—C10i—Br2i | 0.6 (4) | N1—C1—C2—C3 | 0.4 (7) |
I1—C8—C10i—C9i | −179.1 (4) | N2—C3—C2—C1 | 179.7 (5) |
Br1—C9—C10—Br2 | −0.4 (4) | N2—C3—C4—C5 | −179.4 (5) |
Br1—C9—C10—C8i | 179.9 (4) | C9—C10—C8i—C9i | −1.1 (4) |
Br1—C9—C8—C10i | −179.9 (4) | C9—C8—C10i—C9i | 1.1 (4) |
Br2—C10—C9—C8 | −179.2 (4) |
Symmetry code: (i) −x+2, −y+2, −z+2. |
2C7H10N2·C6BrF4I | F(000) = 584.861 |
Mr = 599.21 | Dx = 1.837 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 7.3898 (1) Å | Cell parameters from 6158 reflections |
b = 16.2120 (2) Å | θ = 2.7–77.2° |
c = 9.4236 (1) Å | µ = 14.21 mm−1 |
β = 106.304 (2)° | T = 100 K |
V = 1083.58 (3) Å3 | Irregular, clear colourless |
Z = 2 | 0.12 × 0.08 × 0.05 mm |
Rigaku XtaLAB Synergy Dualflex diffractometer with a HyPix detector | 2300 independent reflections |
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source | 2252 reflections with I ≥ 2u(I) |
Mirror monochromator | Rint = 0.042 |
Detector resolution: 10.0000 pixels mm-1 | θmax = 77.8°, θmin = 5.5° |
ω scans | h = −9→8 |
Absorption correction: analytical (CrysAlis PRO; Rigaku OD, 2023) | k = −20→20 |
Tmin = 0.357, Tmax = 0.595 | l = −11→11 |
10454 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.034 | w = 1/[σ2(Fo2) + (0.P)2 + 7.3962P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.080 | (Δ/σ)max = −0.0003 |
S = 1.00 | Δρmax = 0.75 e Å−3 |
2300 reflections | Δρmin = −0.58 e Å−3 |
142 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
2 restraints | Extinction coefficient: 0.00052 (12) |
17 constraints |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Br1 | 0.5971 (11) | 0.1994 (3) | 0.5192 (9) | 0.0152 (3) | 0.500000 |
F1 | 0.8516 (3) | 0.05177 (14) | 0.5086 (3) | 0.0208 (5) | |
F2 | 0.7755 (3) | −0.10968 (14) | 0.4932 (3) | 0.0225 (5) | |
N2 | 0.8291 (5) | 0.6174 (2) | 0.5179 (4) | 0.0232 (7) | |
N1 | 0.6838 (5) | 0.3679 (2) | 0.5376 (4) | 0.0223 (7) | |
C9 | 0.6759 (5) | 0.0271 (2) | 0.5040 (4) | 0.0166 (7) | |
C8 | 0.5400 (5) | 0.0856 (2) | 0.5067 (4) | 0.0165 (7) | |
C3 | 0.7814 (5) | 0.5370 (2) | 0.5251 (4) | 0.0182 (7) | |
C4 | 0.8329 (5) | 0.4914 (2) | 0.6585 (4) | 0.0196 (8) | |
H4 | 0.9035 (5) | 0.5168 (2) | 0.7478 (4) | 0.0236 (9)* | |
C10 | 0.6374 (5) | −0.0562 (2) | 0.4966 (4) | 0.0171 (7) | |
C1 | 0.6320 (6) | 0.4122 (3) | 0.4111 (4) | 0.0220 (8) | |
H1 | 0.5583 (6) | 0.3852 (3) | 0.3247 (4) | 0.0264 (10)* | |
C5 | 0.7796 (6) | 0.4098 (3) | 0.6572 (5) | 0.0215 (8) | |
H5 | 0.8137 (6) | 0.3811 (3) | 0.7488 (5) | 0.0258 (10)* | |
C2 | 0.6781 (6) | 0.4934 (2) | 0.3983 (4) | 0.0200 (8) | |
H2 | 0.6407 (6) | 0.5202 (2) | 0.3049 (4) | 0.0241 (9)* | |
C6 | 0.7750 (6) | 0.6616 (3) | 0.3788 (5) | 0.0255 (9) | |
H6a | 0.826 (4) | 0.6332 (11) | 0.3067 (12) | 0.0383 (13)* | |
H6b | 0.6371 (6) | 0.6635 (18) | 0.3418 (19) | 0.0383 (13)* | |
H6c | 0.825 (4) | 0.7179 (7) | 0.3937 (9) | 0.0383 (13)* | |
C7 | 0.9279 (7) | 0.6620 (3) | 0.6521 (5) | 0.0289 (9) | |
H7a | 0.853 (2) | 0.6603 (19) | 0.7228 (16) | 0.0433 (14)* | |
H7b | 1.051 (2) | 0.6362 (13) | 0.696 (2) | 0.0433 (14)* | |
H7c | 0.946 (4) | 0.7195 (6) | 0.6272 (8) | 0.0433 (14)* | |
I1 | 0.6049 (7) | 0.21223 (17) | 0.5197 (5) | 0.0152 (3) | 0.500000 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0184 (4) | 0.0075 (9) | 0.01871 (18) | −0.0009 (7) | 0.0037 (2) | −0.0006 (7) |
F1 | 0.0143 (10) | 0.0228 (12) | 0.0258 (12) | −0.0028 (9) | 0.0063 (9) | −0.0008 (9) |
F2 | 0.0177 (11) | 0.0188 (11) | 0.0314 (13) | 0.0042 (9) | 0.0077 (9) | −0.0014 (9) |
N2 | 0.0305 (18) | 0.0171 (16) | 0.0202 (17) | −0.0049 (14) | 0.0042 (14) | 0.0000 (13) |
N1 | 0.0174 (15) | 0.0232 (18) | 0.0257 (18) | 0.0008 (13) | 0.0051 (13) | 0.0012 (14) |
C9 | 0.0152 (16) | 0.0190 (19) | 0.0140 (17) | −0.0041 (14) | 0.0015 (13) | 0.0014 (14) |
C8 | 0.0175 (17) | 0.0146 (17) | 0.0170 (18) | −0.0014 (14) | 0.0042 (14) | −0.0003 (14) |
C3 | 0.0187 (17) | 0.0188 (18) | 0.0191 (18) | −0.0002 (15) | 0.0086 (15) | −0.0031 (15) |
C4 | 0.0200 (18) | 0.0194 (19) | 0.0197 (19) | 0.0003 (15) | 0.0058 (15) | −0.0010 (15) |
C10 | 0.0177 (17) | 0.0175 (18) | 0.0167 (18) | 0.0023 (14) | 0.0057 (14) | 0.0005 (14) |
C1 | 0.0222 (19) | 0.026 (2) | 0.0180 (19) | 0.0003 (16) | 0.0055 (15) | −0.0035 (16) |
C5 | 0.0233 (19) | 0.022 (2) | 0.0194 (19) | 0.0020 (16) | 0.0062 (15) | 0.0009 (15) |
C2 | 0.0239 (19) | 0.0200 (19) | 0.0154 (18) | −0.0003 (15) | 0.0041 (15) | 0.0006 (15) |
C6 | 0.033 (2) | 0.019 (2) | 0.025 (2) | 0.0001 (17) | 0.0101 (18) | 0.0021 (16) |
C7 | 0.036 (2) | 0.020 (2) | 0.027 (2) | −0.0085 (18) | 0.0041 (19) | −0.0047 (17) |
I1 | 0.0184 (4) | 0.0075 (9) | 0.01871 (18) | −0.0009 (7) | 0.0037 (2) | −0.0006 (7) |
Br1—C8 | 1.888 (6) | C3—C2 | 1.413 (5) |
Br1—I1 | 0.216 (8) | C4—H4 | 0.9500 |
F1—C9 | 1.348 (4) | C4—C5 | 1.380 (6) |
F2—C10 | 1.346 (4) | C1—H1 | 0.9500 |
N2—C3 | 1.358 (5) | C1—C2 | 1.373 (6) |
N2—C6 | 1.448 (5) | C5—H5 | 0.9500 |
N2—C7 | 1.462 (5) | C2—H2 | 0.9500 |
N1—C1 | 1.352 (5) | C6—H6a | 0.9800 |
N1—C5 | 1.336 (5) | C6—H6b | 0.9800 |
C9—C8 | 1.388 (5) | C6—H6c | 0.9800 |
C9—C10 | 1.377 (5) | C7—H7a | 0.9800 |
C8—C10i | 1.387 (5) | C7—H7b | 0.9800 |
C8—I1 | 2.103 (5) | C7—H7c | 0.9800 |
C3—C4 | 1.415 (6) | ||
C6—N2—C3 | 120.7 (3) | H1—C1—N1 | 117.6 (2) |
C7—N2—C3 | 120.4 (3) | C2—C1—N1 | 124.8 (4) |
C7—N2—C6 | 118.8 (3) | C2—C1—H1 | 117.6 (2) |
C5—N1—C1 | 115.2 (4) | C4—C5—N1 | 125.2 (4) |
C8—C9—F1 | 119.4 (3) | H5—C5—N1 | 117.4 (2) |
C10—C9—F1 | 118.4 (3) | H5—C5—C4 | 117.4 (2) |
C10—C9—C8 | 122.1 (3) | C1—C2—C3 | 119.5 (4) |
C9—C8—Br1 | 121.3 (4) | H2—C2—C3 | 120.2 (2) |
C10i—C8—Br1 | 122.1 (4) | H2—C2—C1 | 120.2 (2) |
C10i—C8—C9 | 116.6 (3) | H6a—C6—N2 | 109.5 |
I1—C8—C9 | 121.0 (3) | H6b—C6—N2 | 109.5 |
I1—C8—C10i | 122.4 (3) | H6b—C6—H6a | 109.5 |
C4—C3—N2 | 122.4 (4) | H6c—C6—N2 | 109.5 |
C2—C3—N2 | 121.6 (4) | H6c—C6—H6a | 109.5 |
C2—C3—C4 | 115.9 (4) | H6c—C6—H6b | 109.5 |
H4—C4—C3 | 120.4 (2) | H7a—C7—N2 | 109.5 |
C5—C4—C3 | 119.2 (4) | H7b—C7—N2 | 109.5 |
C5—C4—H4 | 120.4 (2) | H7b—C7—H7a | 109.5 |
C9—C10—F2 | 119.0 (3) | H7c—C7—N2 | 109.5 |
C8i—C10—F2 | 119.7 (3) | H7c—C7—H7a | 109.5 |
C8i—C10—C9 | 121.2 (4) | H7c—C7—H7b | 109.5 |
Br1—C8—C9—F1 | −0.8 (4) | F2—C10—C8i—C9i | −179.6 (3) |
Br1—C8—C9—C10 | 179.3 (4) | F2—C10—C8i—I1i | −0.8 (4) |
Br1—C8—C10i—F2i | 1.1 (5) | N2—C3—C4—C5 | −179.9 (4) |
Br1—C8—C10i—C9i | −179.2 (4) | N2—C3—C2—C1 | −179.6 (4) |
F1—C9—C8—C10i | −179.3 (3) | N1—C1—C2—C3 | −2.4 (5) |
F1—C9—C8—I1 | −0.5 (4) | N1—C5—C4—C3 | 1.4 (5) |
F1—C9—C10—F2 | −0.5 (4) | C9—C8—C10i—C9i | −0.7 (3) |
F1—C9—C10—C8i | 179.2 (3) | C9—C10—C8i—C9i | 0.7 (4) |
F2—C10—C9—C8 | 179.5 (3) | C9—C10—C8i—I1i | 179.5 (3) |
Symmetry code: (i) −x+1, −y, −z+1. |
2C7H10N2·C6Br2F2I2 | Z = 2 |
Mr = 768.02 | F(000) = 723.788 |
Triclinic, P1 | Dx = 2.169 Mg m−3 |
a = 9.6158 (4) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 9.7518 (4) Å | Cell parameters from 12656 reflections |
c = 14.8423 (7) Å | θ = 3.1–77.0° |
α = 74.473 (4)° | µ = 25.26 mm−1 |
β = 85.820 (4)° | T = 100 K |
γ = 61.476 (4)° | Plate, clear colourless |
V = 1175.73 (10) Å3 | 0.23 × 0.1 × 0.04 mm |
Rigaku XtaLAB Synergy Dualflex diffractometer with a HyPix detector | 4962 independent reflections |
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source | 4694 reflections with I ≥ 2u(I) |
Mirror monochromator | Rint = 0.063 |
Detector resolution: 10.0000 pixels mm-1 | θmax = 78.5°, θmin = 3.1° |
ω scans | h = −11→12 |
Absorption correction: analytical (CrysAlis PRO; Rigaku OD, 2023) | k = −12→12 |
Tmin = 0.055, Tmax = 0.441 | l = −18→18 |
22021 measured reflections |
Refinement on F2 | 32 constraints |
Least-squares matrix: full | Primary atom site location: dual |
R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.142 | w = 1/[σ2(Fo2) + (0.1145P)2 + 0.3489P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = −0.0004 |
4962 reflections | Δρmax = 3.00 e Å−3 |
275 parameters | Δρmin = −1.94 e Å−3 |
0 restraints |
x | y | z | Uiso*/Ueq | ||
I1 | 0.40062 (3) | 0.97911 (4) | 0.70655 (2) | 0.02939 (14) | |
I2 | 0.79056 (4) | 0.12383 (4) | 0.81263 (2) | 0.03182 (14) | |
Br2 | 0.54649 (6) | 0.76869 (6) | 0.53272 (3) | 0.02882 (15) | |
Br1 | 0.72000 (6) | 0.37330 (6) | 0.58100 (4) | 0.03075 (16) | |
F1 | 0.4850 (4) | 0.6969 (4) | 0.8923 (2) | 0.0365 (7) | |
F2 | 0.6273 (4) | 0.3785 (4) | 0.9317 (2) | 0.0396 (7) | |
N1 | 0.2482 (6) | 1.3018 (6) | 0.6717 (4) | 0.0349 (10) | |
N2 | 0.0075 (6) | 1.8081 (7) | 0.6108 (4) | 0.0360 (10) | |
N3 | 0.9490 (6) | −0.2038 (6) | 0.8602 (4) | 0.0376 (10) | |
N4 | 1.1802 (6) | −0.7074 (7) | 0.9133 (4) | 0.0392 (11) | |
C12 | 0.6494 (5) | 0.4759 (6) | 0.6795 (3) | 0.0257 (9) | |
C8 | 0.5171 (6) | 0.7235 (6) | 0.7292 (4) | 0.0262 (9) | |
C1 | 0.2447 (6) | 1.5495 (7) | 0.6697 (4) | 0.0290 (10) | |
C5 | 0.0864 (6) | 1.6428 (7) | 0.6311 (3) | 0.0272 (9) | |
C13 | 0.5739 (5) | 0.6440 (6) | 0.6585 (3) | 0.0251 (9) | |
C11 | 0.6720 (6) | 0.3808 (6) | 0.7722 (4) | 0.0267 (10) | |
C3 | 0.0972 (6) | 1.3892 (7) | 0.6354 (4) | 0.0336 (11) | |
C9 | 0.5373 (6) | 0.6278 (7) | 0.8202 (4) | 0.0311 (10) | |
C4 | 0.0143 (6) | 1.5545 (7) | 0.6148 (4) | 0.0313 (10) | |
C2 | 0.3179 (6) | 1.3846 (7) | 0.6872 (4) | 0.0334 (11) | |
C10 | 0.6122 (6) | 0.4623 (7) | 0.8411 (4) | 0.0321 (10) | |
C17 | 0.9472 (6) | −0.4472 (7) | 0.8581 (4) | 0.0347 (11) | |
C16 | 0.8784 (7) | −0.2829 (8) | 0.8424 (4) | 0.0380 (12) | |
C15 | 1.1001 (7) | −0.2938 (7) | 0.8956 (4) | 0.0352 (11) | |
C18 | 1.1063 (6) | −0.5444 (7) | 0.8958 (4) | 0.0304 (10) | |
C14 | 1.1818 (6) | −0.4598 (7) | 0.9140 (4) | 0.0333 (11) | |
C6 | −0.1606 (6) | 1.8945 (7) | 0.5886 (5) | 0.0383 (12) | |
C7 | 0.0866 (6) | 1.8924 (7) | 0.6323 (4) | 0.0352 (11) | |
C19 | 1.0981 (8) | −0.7907 (8) | 0.8951 (5) | 0.0424 (13) | |
C20 | 1.3464 (8) | −0.8058 (8) | 0.9470 (6) | 0.0496 (16) | |
H1 | 0.2999 (6) | 1.6011 (7) | 0.6834 (4) | 0.0348 (12)* | |
H4 | −0.0923 (6) | 1.6100 (7) | 0.5894 (4) | 0.0376 (12)* | |
H14 | 1.2888 (6) | −0.5176 (7) | 0.9388 (4) | 0.0400 (13)* | |
H17 | 0.8890 (6) | −0.4956 (7) | 0.8438 (4) | 0.0417 (13)* | |
H6a | −0.1829 (7) | 1.887 (6) | 0.5273 (18) | 0.0575 (18)* | |
H6b | −0.2125 (9) | 1.847 (4) | 0.637 (2) | 0.0575 (18)* | |
H6c | −0.2011 (12) | 2.0085 (15) | 0.587 (4) | 0.0575 (18)* | |
H7a | 0.101 (6) | 1.869 (5) | 0.7005 (4) | 0.0529 (17)* | |
H7b | 0.190 (3) | 1.856 (5) | 0.605 (3) | 0.0529 (17)* | |
H7c | 0.021 (3) | 2.0093 (8) | 0.606 (3) | 0.0529 (17)* | |
H19a | 1.002 (4) | −0.763 (6) | 0.930 (3) | 0.0636 (19)* | |
H19b | 1.069 (6) | −0.758 (5) | 0.8279 (7) | 0.0636 (19)* | |
H19c | 1.168 (3) | −0.9079 (8) | 0.915 (4) | 0.0636 (19)* | |
H20a | 1.4084 (14) | −0.757 (4) | 0.910 (3) | 0.074 (2)* | |
H20b | 1.3569 (12) | −0.811 (7) | 1.0132 (14) | 0.074 (2)* | |
H20c | 1.386 (2) | −0.915 (2) | 0.940 (4) | 0.074 (2)* | |
H3 | 0.0454 (6) | 1.3331 (7) | 0.6235 (4) | 0.0403 (13)* | |
H2 | 0.4250 (6) | 1.3250 (7) | 0.7119 (4) | 0.0400 (13)* | |
H15 | 1.1535 (7) | −0.2400 (7) | 0.9087 (4) | 0.0422 (13)* | |
H16 | 0.7718 (7) | −0.2206 (8) | 0.8168 (4) | 0.0456 (14)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.0264 (2) | 0.0275 (2) | 0.0354 (2) | −0.01116 (15) | −0.00138 (12) | −0.01253 (14) |
I2 | 0.0300 (2) | 0.0277 (2) | 0.0357 (2) | −0.01197 (16) | −0.00371 (13) | −0.00713 (14) |
Br2 | 0.0297 (3) | 0.0295 (3) | 0.0269 (3) | −0.0135 (2) | −0.00174 (18) | −0.0074 (2) |
Br1 | 0.0323 (3) | 0.0306 (3) | 0.0308 (3) | −0.0132 (2) | 0.00128 (19) | −0.0139 (2) |
F1 | 0.0482 (17) | 0.0334 (16) | 0.0300 (14) | −0.0177 (14) | 0.0055 (12) | −0.0162 (12) |
F2 | 0.0489 (17) | 0.0399 (18) | 0.0280 (14) | −0.0198 (15) | 0.0013 (12) | −0.0080 (13) |
N1 | 0.033 (2) | 0.034 (3) | 0.038 (2) | −0.013 (2) | −0.0033 (18) | −0.013 (2) |
N2 | 0.028 (2) | 0.037 (3) | 0.044 (3) | −0.013 (2) | −0.0039 (18) | −0.017 (2) |
N3 | 0.038 (2) | 0.030 (2) | 0.042 (3) | −0.015 (2) | −0.0056 (19) | −0.0049 (19) |
N4 | 0.035 (2) | 0.034 (3) | 0.043 (3) | −0.011 (2) | −0.009 (2) | −0.010 (2) |
C12 | 0.024 (2) | 0.026 (2) | 0.032 (2) | −0.0121 (18) | 0.0011 (16) | −0.0142 (19) |
C8 | 0.0194 (19) | 0.026 (2) | 0.033 (2) | −0.0094 (19) | −0.0002 (16) | −0.0105 (19) |
C1 | 0.028 (2) | 0.035 (3) | 0.031 (2) | −0.019 (2) | 0.0023 (18) | −0.013 (2) |
C5 | 0.024 (2) | 0.028 (2) | 0.027 (2) | −0.0095 (19) | 0.0007 (16) | −0.0100 (19) |
C13 | 0.027 (2) | 0.027 (2) | 0.0214 (19) | −0.0140 (19) | −0.0010 (15) | −0.0037 (17) |
C11 | 0.026 (2) | 0.021 (2) | 0.034 (2) | −0.0109 (19) | 0.0000 (18) | −0.0077 (19) |
C3 | 0.029 (2) | 0.038 (3) | 0.039 (3) | −0.017 (2) | −0.0026 (19) | −0.016 (2) |
C9 | 0.030 (2) | 0.037 (3) | 0.032 (2) | −0.015 (2) | 0.0013 (18) | −0.019 (2) |
C4 | 0.024 (2) | 0.034 (3) | 0.037 (2) | −0.013 (2) | −0.0007 (18) | −0.012 (2) |
C2 | 0.025 (2) | 0.036 (3) | 0.040 (3) | −0.013 (2) | −0.0026 (19) | −0.014 (2) |
C10 | 0.034 (2) | 0.039 (3) | 0.026 (2) | −0.020 (2) | −0.0008 (18) | −0.006 (2) |
C17 | 0.030 (2) | 0.037 (3) | 0.037 (3) | −0.016 (2) | 0.000 (2) | −0.008 (2) |
C16 | 0.032 (2) | 0.039 (3) | 0.037 (3) | −0.013 (2) | −0.005 (2) | −0.006 (2) |
C15 | 0.038 (3) | 0.034 (3) | 0.035 (2) | −0.018 (2) | −0.001 (2) | −0.009 (2) |
C18 | 0.030 (2) | 0.031 (3) | 0.026 (2) | −0.010 (2) | −0.0016 (18) | −0.009 (2) |
C14 | 0.029 (2) | 0.034 (3) | 0.035 (2) | −0.013 (2) | −0.0021 (19) | −0.010 (2) |
C6 | 0.027 (2) | 0.030 (3) | 0.051 (3) | −0.007 (2) | −0.003 (2) | −0.012 (2) |
C7 | 0.031 (2) | 0.030 (3) | 0.048 (3) | −0.013 (2) | 0.002 (2) | −0.017 (2) |
C19 | 0.043 (3) | 0.037 (3) | 0.048 (3) | −0.017 (3) | 0.002 (2) | −0.016 (3) |
C20 | 0.037 (3) | 0.031 (3) | 0.069 (4) | −0.002 (2) | −0.009 (3) | −0.016 (3) |
I1—C8 | 2.127 (5) | C3—C4 | 1.368 (8) |
I2—C11 | 2.123 (5) | C3—H3 | 0.9500 |
Br2—C13 | 1.894 (5) | C9—C10 | 1.369 (8) |
Br1—C12 | 1.894 (5) | C4—H4 | 0.9500 |
F1—C9 | 1.354 (6) | C2—H2 | 0.9500 |
F2—C10 | 1.351 (6) | C17—C16 | 1.367 (9) |
N1—C3 | 1.346 (7) | C17—C18 | 1.417 (7) |
N1—C2 | 1.338 (8) | C17—H17 | 0.9500 |
N2—C5 | 1.368 (8) | C16—H16 | 0.9500 |
N2—C6 | 1.435 (7) | C15—C14 | 1.375 (8) |
N2—C7 | 1.459 (8) | C15—H15 | 0.9500 |
N3—C16 | 1.327 (8) | C18—C14 | 1.414 (8) |
N3—C15 | 1.343 (8) | C14—H14 | 0.9500 |
N4—C18 | 1.352 (8) | C6—H6a | 0.9800 |
N4—C19 | 1.455 (8) | C6—H6b | 0.9800 |
N4—C20 | 1.456 (8) | C6—H6c | 0.9800 |
C12—C13 | 1.391 (7) | C7—H7a | 0.9800 |
C12—C11 | 1.403 (7) | C7—H7b | 0.9800 |
C8—C13 | 1.394 (7) | C7—H7c | 0.9800 |
C8—C9 | 1.388 (8) | C19—H19a | 0.9800 |
C1—C5 | 1.414 (7) | C19—H19b | 0.9800 |
C1—C2 | 1.368 (8) | C19—H19c | 0.9800 |
C1—H1 | 0.9500 | C20—H20a | 0.9800 |
C5—C4 | 1.409 (8) | C20—H20b | 0.9800 |
C11—C10 | 1.385 (8) | C20—H20c | 0.9800 |
C2—N1—C3 | 116.7 (5) | C9—C10—C11 | 121.8 (5) |
C6—N2—C5 | 119.9 (5) | C18—C17—C16 | 119.2 (5) |
C7—N2—C5 | 119.3 (5) | H17—C17—C16 | 120.4 (3) |
C7—N2—C6 | 119.3 (5) | H17—C17—C18 | 120.4 (3) |
C15—N3—C16 | 116.6 (5) | C17—C16—N3 | 125.1 (5) |
C19—N4—C18 | 121.0 (5) | H16—C16—N3 | 117.5 (3) |
C20—N4—C18 | 121.5 (5) | H16—C16—C17 | 117.5 (3) |
C20—N4—C19 | 117.4 (5) | C14—C15—N3 | 123.5 (5) |
C13—C12—Br1 | 119.5 (4) | H15—C15—N3 | 118.2 (3) |
C11—C12—Br1 | 119.3 (4) | H15—C15—C14 | 118.2 (3) |
C11—C12—C13 | 121.2 (5) | C17—C18—N4 | 121.8 (5) |
C13—C8—I1 | 124.6 (4) | C14—C18—N4 | 122.5 (5) |
C9—C8—I1 | 118.2 (4) | C14—C18—C17 | 115.7 (5) |
C9—C8—C13 | 117.1 (5) | C18—C14—C15 | 119.9 (5) |
C2—C1—C5 | 119.7 (5) | H14—C14—C15 | 120.0 (3) |
H1—C1—C5 | 120.2 (3) | H14—C14—C18 | 120.0 (3) |
H1—C1—C2 | 120.2 (3) | H6a—C6—N2 | 109.5 |
C1—C5—N2 | 122.4 (5) | H6b—C6—N2 | 109.5 |
C4—C5—N2 | 121.9 (5) | H6b—C6—H6a | 109.5 |
C4—C5—C1 | 115.7 (5) | H6c—C6—N2 | 109.5 |
C12—C13—Br2 | 120.1 (4) | H6c—C6—H6a | 109.5 |
C8—C13—Br2 | 118.9 (4) | H6c—C6—H6b | 109.5 |
C8—C13—C12 | 120.9 (4) | H7a—C7—N2 | 109.5 |
C12—C11—I2 | 124.4 (4) | H7b—C7—N2 | 109.5 |
C10—C11—I2 | 118.7 (4) | H7b—C7—H7a | 109.5 |
C10—C11—C12 | 116.9 (5) | H7c—C7—N2 | 109.5 |
C4—C3—N1 | 123.5 (5) | H7c—C7—H7a | 109.5 |
H3—C3—N1 | 118.3 (3) | H7c—C7—H7b | 109.5 |
H3—C3—C4 | 118.3 (3) | H19a—C19—N4 | 109.5 |
C8—C9—F1 | 120.3 (5) | H19b—C19—N4 | 109.5 |
C10—C9—F1 | 117.7 (5) | H19b—C19—H19a | 109.5 |
C10—C9—C8 | 122.0 (5) | H19c—C19—N4 | 109.5 |
C3—C4—C5 | 120.2 (5) | H19c—C19—H19a | 109.5 |
H4—C4—C5 | 119.9 (3) | H19c—C19—H19b | 109.5 |
H4—C4—C3 | 119.9 (3) | H20a—C20—N4 | 109.5 |
C1—C2—N1 | 124.2 (5) | H20b—C20—N4 | 109.5 |
H2—C2—N1 | 117.9 (3) | H20b—C20—H20a | 109.5 |
H2—C2—C1 | 117.9 (3) | H20c—C20—N4 | 109.5 |
C11—C10—F2 | 120.1 (5) | H20c—C20—H20a | 109.5 |
C9—C10—F2 | 118.1 (5) | H20c—C20—H20b | 109.5 |
I1—C8—C13—Br2 | −0.3 (4) | F2—C10—C11—C12 | 178.9 (5) |
I1—C8—C13—C12 | 179.7 (4) | F2—C10—C9—C8 | 179.7 (4) |
I1—C8—C9—F1 | −0.7 (4) | N1—C3—C4—C5 | 0.2 (7) |
I1—C8—C9—C10 | −179.4 (4) | N1—C2—C1—C5 | −1.3 (7) |
I2—C11—C12—Br1 | 2.7 (4) | N2—C5—C1—C2 | −179.1 (5) |
I2—C11—C12—C13 | −178.4 (4) | N2—C5—C4—C3 | 179.6 (5) |
I2—C11—C10—F2 | −1.2 (4) | N3—C16—C17—C18 | −0.3 (7) |
I2—C11—C10—C9 | 178.7 (4) | N3—C15—C14—C18 | −0.2 (7) |
Br2—C13—C12—Br1 | −1.5 (4) | N4—C18—C17—C16 | 179.6 (6) |
Br2—C13—C12—C11 | 179.6 (4) | N4—C18—C14—C15 | −179.3 (6) |
Br2—C13—C8—C9 | 179.0 (4) | C12—C13—C8—C9 | −1.0 (5) |
Br1—C12—C13—C8 | 178.5 (3) | C12—C11—C10—C9 | −1.3 (6) |
Br1—C12—C11—C10 | −177.4 (4) | C8—C9—C10—C11 | −0.2 (6) |
F1—C9—C8—C13 | 180.0 (5) | C1—C5—C4—C3 | −0.5 (6) |
F1—C9—C10—F2 | 1.0 (5) | C17—C18—C14—C15 | 0.5 (6) |
F1—C9—C10—C11 | −178.9 (4) |
Perhalobenzene | DITFBa | DITCB | DITBB | IBTFB | DIBFB |
N···I | 2.6622 (4) | 2.698 (4) | 2.708 (5) | 2.588 (5) I | 2.675 (5) |
2.797 (6) Br | 2.707 (5) | ||||
C—-I···N | 179.323 (14) | 178.08 (13) | 178.48 (16) | 179.5 (3) | 178.11 (18) |
177.71 (18) | |||||
Cp—N···Ib | 172.92 (2) | 172.67 (17) | 174.9 (2) | 173.2 (2) | 175.5 (3) |
175.5 (3) | |||||
CX6···DMAP | 79.17 (2) | 86.6 (16) | 82.4 (5) | 78.6 (4) | 76.59 (19) |
76.3 (2) |
Notes: (a) data from CSD refcode RUYHID02 collected at 100 K (Wang et al., 2018); (b) Cp is the pyridyl C atom para to the pyridyl N atom. |
XB donor | H···Ha,b | C···Xa | C···Ca | H···Ca,b | H···Xa | H···Ia | N···Ia |
DITCB | 35.5 | 3.3 | 3.4 | 20.9 | 17.6 | 7.7 | 3.0 |
DITBB | 37.0 | 4.0 | 3.3 | 20.2 | 16.4 | 7.6 | 3.0 |
DIBFB | 35.8 | 4.5 (Br) | 3.4 | 20.3 | 16.0 (Br) | 8.2 | 3.1 |
0.0 (F) | 0.0 (F) | ||||||
DITFB | 34.3 | 0.0 | 5.3 | 21.3 | 17.5 | 8.2 | 3.0 |
Notes: (a) the first element listed corresponds to the DMAP molecule, while the second element is an element with a close contact from outside the DMAP molecule. (b) Includes reciprocal contacts. Part corresponds to a DMAP methyl–H contact with the C atom of a π-stacked DMAP molecule and part corresponds to the DMAP pyridyl–H contact to a C atom of C6X6. |
XB donor | X···Ha | I···H | C···H | X···X | I···Xb | I···N |
DITCB | 37.2 | 26.5 | 16.0 | 4.3 | 3.9 | 5.3 |
DITBB | 36.0 | 25.1 | 15.9 | 5.8 | 3.9 | 5.0 |
DIBFB | 19.0 (Br) | 29.9 | 16.0 | 3.8 (Br) | 2.1 (Br) | 5.4 |
15.5 (F) | 3.3 (F) | 0.0 (F) | ||||
DITFB | 34.6 | 35.1 | 16.6 | 7.4 | 0.0 | 6.2 |
Notes: (a) the first element listed corresponds to the CI2X4 molecule, while the second is an element with a close contact from outside the CI2X4 molecule; (b) includes reciprocal contacts. |
Halobenzene major interaction | DITCB | DITBB | DIBFB |
DMAP π–π stackinga | -36.8 | -36.9 | -37.0, -36.9d |
DMAP offset π–π stackedb | -15.4 | -13.8 | -12.8 |
Halogen bond (N···I)c | -29.9 (76.4) | -29.5 (76.7) | -32.2 (75.8, 76.6) |
C—H···π (C6X6) | -19.7 | -22.0 | -21.1 |
C—X···π (DMAP) | -9.6 | -15.4 | -15.9 (X = Br) |
Notes: (a) corresponds to pairs of DMAP molecules with maximum π–π overlap. (b) Mainly methyl–methyl interactions. (c) N···I separation as a % of the van der Waals radii in parentheses. (d) The second value corresponds to the inner two DMAP molecules, labeled `y2' in Fig. 6(b). |