Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229624002018/vp3032sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229624002018/vp3032L2.C2H5OHsup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229624002018/vp3032L3sup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229624002018/vp3032L4sup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229624002018/vp3032L5sup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229624002018/vp3032L6sup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229624002018/vp3032L2_autosup7.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229624002018/vp3032L2.C2H5OHsup8.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229624002018/vp3032L3sup9.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229624002018/vp3032L4sup10.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229624002018/vp3032L5sup11.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229624002018/vp3032L6sup12.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229624002018/vp3032L2_autosup13.cml | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229624002018/vp3032sup14.pdf |
CCDC references: 2336435; 2336434; 2336433; 2336432; 2336431; 2336430
C18H14N6·C2H6O | Z = 2 |
Mr = 360.42 | F(000) = 380 |
Triclinic, P1 | Dx = 1.277 Mg m−3 |
a = 9.455 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.628 (8) Å | Cell parameters from 1462 reflections |
c = 12.023 (10) Å | θ = 2.4–21.7° |
α = 69.506 (10)° | µ = 0.08 mm−1 |
β = 79.904 (12)° | T = 293 K |
γ = 66.215 (11)° | Block, clear light colourless |
V = 937.3 (13) Å3 | 0.19 × 0.15 × 0.11 mm |
Bruker APEXII CCD area detector diffractometer | 2042 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
phi and ω scans | θmax = 25.1°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −11→11 |
Tmin = 0.984, Tmax = 0.991 | k = −11→11 |
6792 measured reflections | l = −13→14 |
3305 independent reflections |
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.063 | H-atom parameters constrained |
wR(F2) = 0.197 | w = 1/[σ2(Fo2) + (0.1138P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
3305 reflections | Δρmax = 0.54 e Å−3 |
247 parameters | Δρmin = −0.31 e Å−3 |
13 restraints |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.9353 (3) | 0.2070 (3) | 0.8372 (2) | 0.0721 (8) | |
N2 | 0.8502 (3) | 0.3247 (3) | 0.5367 (2) | 0.0565 (7) | |
N3 | 0.7357 (3) | 0.3032 (3) | 0.49514 (19) | 0.0558 (7) | |
N4 | 0.6887 (2) | 0.2718 (2) | 0.68607 (17) | 0.0424 (6) | |
N5 | 0.4824 (3) | 0.1168 (3) | 0.6702 (2) | 0.0570 (7) | |
N6 | 0.4419 (3) | 0.2999 (3) | 0.4735 (2) | 0.0604 (7) | |
C1 | 1.0356 (5) | 0.2029 (5) | 0.9042 (3) | 0.0923 (13) | |
H1 | 1.047673 | 0.132340 | 0.981106 | 0.111* | |
C2 | 1.1231 (4) | 0.2976 (5) | 0.8658 (4) | 0.0908 (12) | |
H2 | 1.192204 | 0.290709 | 0.915696 | 0.109* | |
C3 | 1.1062 (4) | 0.4001 (4) | 0.7547 (4) | 0.0779 (10) | |
H3 | 1.163903 | 0.465035 | 0.726720 | 0.093* | |
C4 | 1.0038 (3) | 0.4084 (4) | 0.6830 (3) | 0.0591 (8) | |
H4 | 0.990150 | 0.479194 | 0.606141 | 0.071* | |
C5 | 0.9216 (3) | 0.3097 (3) | 0.7270 (3) | 0.0519 (7) | |
C6 | 0.8202 (3) | 0.3051 (3) | 0.6501 (2) | 0.0465 (7) | |
C7 | 0.6405 (3) | 0.2726 (3) | 0.5852 (2) | 0.0451 (7) | |
C8 | 0.5107 (3) | 0.2293 (3) | 0.5769 (2) | 0.0454 (7) | |
C9 | 0.3336 (4) | 0.2493 (4) | 0.4644 (3) | 0.0678 (9) | |
H9 | 0.282112 | 0.294333 | 0.393682 | 0.081* | |
C10 | 0.2944 (3) | 0.1352 (4) | 0.5532 (3) | 0.0663 (9) | |
H10 | 0.218794 | 0.101512 | 0.544282 | 0.080* | |
C11 | 0.3715 (3) | 0.0727 (4) | 0.6558 (3) | 0.0670 (9) | |
H11 | 0.345771 | −0.003971 | 0.718614 | 0.080* | |
C12 | 0.5992 (3) | 0.2806 (3) | 0.7965 (2) | 0.0409 (6) | |
C13 | 0.6242 (3) | 0.1473 (4) | 0.8948 (2) | 0.0576 (8) | |
H13 | 0.694940 | 0.048344 | 0.890597 | 0.069* | |
C14 | 0.5430 (4) | 0.1625 (4) | 0.9996 (2) | 0.0645 (9) | |
H14 | 0.559807 | 0.072510 | 1.066172 | 0.077* | |
C15 | 0.4374 (4) | 0.3076 (4) | 1.0082 (2) | 0.0571 (8) | |
C16 | 0.4129 (3) | 0.4379 (4) | 0.9081 (3) | 0.0585 (8) | |
H16 | 0.340327 | 0.536496 | 0.911420 | 0.070* | |
C17 | 0.4947 (3) | 0.4252 (3) | 0.8015 (2) | 0.0496 (7) | |
H17 | 0.478021 | 0.514711 | 0.734484 | 0.060* | |
C18 | 0.3492 (5) | 0.3233 (5) | 1.1240 (3) | 0.0936 (13) | |
H18A | 0.295129 | 0.251033 | 1.151200 | 0.140* | |
H18B | 0.276236 | 0.430790 | 1.111696 | 0.140* | |
H18C | 0.420407 | 0.297986 | 1.182579 | 0.140* | |
O1 | 0.7849 (3) | 0.1999 (4) | 0.2878 (2) | 0.0960 (8) | |
H1A | 0.772421 | 0.235221 | 0.343189 | 0.144* | |
C19 | 1.0594 (5) | 0.1292 (6) | 0.3210 (5) | 0.1319 (18) | |
H19A | 1.157812 | 0.100920 | 0.279131 | 0.198* | |
H19B | 1.059019 | 0.041673 | 0.390943 | 0.198* | |
H19C | 1.041388 | 0.221420 | 0.343545 | 0.198* | |
C20 | 0.9376 (6) | 0.1648 (7) | 0.2443 (4) | 0.1362 (19) | |
H20A | 0.939953 | 0.254738 | 0.175537 | 0.163* | |
H20B | 0.965645 | 0.074129 | 0.215827 | 0.163* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0834 (18) | 0.086 (2) | 0.0587 (16) | −0.0527 (16) | −0.0174 (14) | −0.0042 (15) |
N2 | 0.0560 (14) | 0.0713 (17) | 0.0470 (14) | −0.0316 (13) | 0.0061 (11) | −0.0184 (12) |
N3 | 0.0571 (14) | 0.0705 (17) | 0.0421 (13) | −0.0289 (13) | 0.0043 (11) | −0.0171 (12) |
N4 | 0.0463 (12) | 0.0467 (13) | 0.0348 (11) | −0.0210 (10) | −0.0006 (9) | −0.0093 (10) |
N5 | 0.0610 (14) | 0.0710 (17) | 0.0456 (14) | −0.0367 (13) | −0.0063 (11) | −0.0093 (12) |
N6 | 0.0627 (15) | 0.0678 (17) | 0.0459 (14) | −0.0200 (13) | −0.0166 (12) | −0.0101 (12) |
C1 | 0.107 (3) | 0.120 (3) | 0.070 (2) | −0.068 (3) | −0.032 (2) | −0.008 (2) |
C2 | 0.078 (2) | 0.112 (3) | 0.107 (3) | −0.053 (2) | −0.020 (2) | −0.035 (3) |
C3 | 0.064 (2) | 0.076 (3) | 0.110 (3) | −0.0412 (19) | −0.001 (2) | −0.031 (2) |
C4 | 0.0516 (16) | 0.0555 (19) | 0.074 (2) | −0.0276 (15) | 0.0051 (15) | −0.0186 (16) |
C5 | 0.0457 (15) | 0.0542 (18) | 0.0591 (18) | −0.0208 (14) | 0.0017 (13) | −0.0205 (15) |
C6 | 0.0452 (15) | 0.0500 (17) | 0.0449 (16) | −0.0216 (13) | 0.0024 (12) | −0.0127 (13) |
C7 | 0.0491 (15) | 0.0501 (17) | 0.0362 (14) | −0.0192 (13) | 0.0001 (12) | −0.0134 (12) |
C8 | 0.0449 (14) | 0.0528 (17) | 0.0371 (14) | −0.0155 (13) | −0.0002 (11) | −0.0160 (13) |
C9 | 0.0621 (19) | 0.086 (3) | 0.0533 (19) | −0.0206 (18) | −0.0179 (15) | −0.0197 (18) |
C10 | 0.0542 (18) | 0.089 (2) | 0.069 (2) | −0.0317 (17) | −0.0082 (16) | −0.0312 (19) |
C11 | 0.0652 (19) | 0.085 (2) | 0.0576 (19) | −0.0400 (18) | −0.0040 (15) | −0.0150 (17) |
C12 | 0.0442 (14) | 0.0494 (17) | 0.0329 (13) | −0.0239 (13) | −0.0047 (11) | −0.0080 (12) |
C13 | 0.0710 (19) | 0.0512 (18) | 0.0466 (17) | −0.0236 (15) | −0.0035 (14) | −0.0088 (14) |
C14 | 0.090 (2) | 0.073 (2) | 0.0361 (16) | −0.047 (2) | 0.0000 (15) | −0.0041 (15) |
C15 | 0.0671 (19) | 0.084 (2) | 0.0418 (16) | −0.0509 (19) | 0.0093 (14) | −0.0231 (16) |
C16 | 0.0587 (17) | 0.067 (2) | 0.0561 (18) | −0.0283 (16) | 0.0104 (14) | −0.0271 (16) |
C17 | 0.0525 (16) | 0.0537 (19) | 0.0440 (16) | −0.0238 (15) | 0.0003 (12) | −0.0129 (13) |
C18 | 0.119 (3) | 0.136 (4) | 0.056 (2) | −0.079 (3) | 0.034 (2) | −0.045 (2) |
O1 | 0.0978 (19) | 0.117 (2) | 0.0848 (19) | −0.0393 (17) | 0.0047 (15) | −0.0490 (17) |
C19 | 0.104 (3) | 0.131 (3) | 0.149 (4) | −0.030 (3) | 0.016 (3) | −0.056 (3) |
C20 | 0.141 (4) | 0.147 (4) | 0.123 (3) | −0.027 (3) | 0.010 (3) | −0.083 (3) |
N1—C1 | 1.329 (4) | C10—C11 | 1.363 (4) |
N1—C5 | 1.337 (4) | C11—H11 | 0.9300 |
N2—N3 | 1.381 (3) | C12—C13 | 1.375 (4) |
N2—C6 | 1.304 (3) | C12—C17 | 1.359 (4) |
N3—C7 | 1.311 (3) | C13—H13 | 0.9300 |
N4—C6 | 1.369 (3) | C13—C14 | 1.377 (4) |
N4—C7 | 1.365 (3) | C14—H14 | 0.9300 |
N4—C12 | 1.453 (3) | C14—C15 | 1.379 (4) |
N5—C8 | 1.334 (3) | C15—C16 | 1.372 (4) |
N5—C11 | 1.335 (4) | C15—C18 | 1.515 (4) |
N6—C8 | 1.329 (3) | C16—H16 | 0.9300 |
N6—C9 | 1.333 (4) | C16—C17 | 1.394 (4) |
C1—H1 | 0.9300 | C17—H17 | 0.9300 |
C1—C2 | 1.382 (5) | C18—H18A | 0.9600 |
C2—H2 | 0.9300 | C18—H18B | 0.9600 |
C2—C3 | 1.345 (5) | C18—H18C | 0.9600 |
C3—H3 | 0.9300 | O1—H1A | 0.8200 |
C3—C4 | 1.367 (5) | O1—C20 | 1.392 (5) |
C4—H4 | 0.9300 | C19—H19A | 0.9600 |
C4—C5 | 1.373 (4) | C19—H19B | 0.9600 |
C5—C6 | 1.467 (4) | C19—H19C | 0.9600 |
C7—C8 | 1.475 (4) | C19—C20 | 1.458 (4) |
C9—H9 | 0.9300 | C20—H20A | 0.9700 |
C9—C10 | 1.361 (4) | C20—H20B | 0.9700 |
C10—H10 | 0.9300 | ||
C1—N1—C5 | 116.3 (3) | N5—C11—H11 | 118.5 |
C6—N2—N3 | 107.1 (2) | C10—C11—H11 | 118.5 |
C7—N3—N2 | 107.5 (2) | C13—C12—N4 | 120.8 (2) |
C6—N4—C12 | 126.3 (2) | C17—C12—N4 | 118.2 (2) |
C7—N4—C6 | 104.3 (2) | C17—C12—C13 | 120.9 (3) |
C7—N4—C12 | 127.2 (2) | C12—C13—H13 | 120.5 |
C8—N5—C11 | 115.0 (2) | C12—C13—C14 | 119.0 (3) |
C8—N6—C9 | 114.6 (3) | C14—C13—H13 | 120.5 |
N1—C1—H1 | 118.2 | C13—C14—H14 | 119.2 |
N1—C1—C2 | 123.6 (4) | C13—C14—C15 | 121.7 (3) |
C2—C1—H1 | 118.2 | C15—C14—H14 | 119.2 |
C1—C2—H2 | 120.7 | C14—C15—C18 | 121.3 (3) |
C3—C2—C1 | 118.5 (3) | C16—C15—C14 | 118.0 (3) |
C3—C2—H2 | 120.7 | C16—C15—C18 | 120.7 (3) |
C2—C3—H3 | 120.2 | C15—C16—H16 | 119.4 |
C2—C3—C4 | 119.7 (3) | C15—C16—C17 | 121.2 (3) |
C4—C3—H3 | 120.2 | C17—C16—H16 | 119.4 |
C3—C4—H4 | 120.8 | C12—C17—C16 | 119.3 (3) |
C3—C4—C5 | 118.5 (3) | C12—C17—H17 | 120.4 |
C5—C4—H4 | 120.8 | C16—C17—H17 | 120.4 |
N1—C5—C4 | 123.3 (3) | C15—C18—H18A | 109.5 |
N1—C5—C6 | 116.3 (3) | C15—C18—H18B | 109.5 |
C4—C5—C6 | 120.2 (3) | C15—C18—H18C | 109.5 |
N2—C6—N4 | 110.8 (2) | H18A—C18—H18B | 109.5 |
N2—C6—C5 | 123.2 (2) | H18A—C18—H18C | 109.5 |
N4—C6—C5 | 125.9 (2) | H18B—C18—H18C | 109.5 |
N3—C7—N4 | 110.3 (2) | C20—O1—H1A | 109.5 |
N3—C7—C8 | 123.0 (2) | H19A—C19—H19B | 109.5 |
N4—C7—C8 | 126.4 (2) | H19A—C19—H19C | 109.5 |
N5—C8—C7 | 116.8 (2) | H19B—C19—H19C | 109.5 |
N6—C8—N5 | 127.4 (3) | C20—C19—H19A | 109.5 |
N6—C8—C7 | 115.6 (2) | C20—C19—H19B | 109.5 |
N6—C9—H9 | 118.3 | C20—C19—H19C | 109.5 |
N6—C9—C10 | 123.5 (3) | O1—C20—C19 | 120.2 (4) |
C10—C9—H9 | 118.3 | O1—C20—H20A | 107.3 |
C9—C10—H10 | 121.7 | O1—C20—H20B | 107.3 |
C9—C10—C11 | 116.6 (3) | C19—C20—H20A | 107.3 |
C11—C10—H10 | 121.7 | C19—C20—H20B | 107.3 |
N5—C11—C10 | 122.9 (3) | H20A—C20—H20B | 106.9 |
N1—C1—C2—C3 | 0.1 (6) | C6—N4—C12—C13 | −94.6 (3) |
N1—C5—C6—N2 | −142.7 (3) | C6—N4—C12—C17 | 82.7 (3) |
N1—C5—C6—N4 | 33.4 (4) | C7—N4—C6—N2 | 0.0 (3) |
N2—N3—C7—N4 | −0.5 (3) | C7—N4—C6—C5 | −176.6 (3) |
N2—N3—C7—C8 | −174.6 (2) | C7—N4—C12—C13 | 104.9 (3) |
N3—N2—C6—N4 | −0.3 (3) | C7—N4—C12—C17 | −77.8 (3) |
N3—N2—C6—C5 | 176.4 (2) | C8—N5—C11—C10 | 1.2 (5) |
N3—C7—C8—N5 | 140.8 (3) | C8—N6—C9—C10 | 0.3 (4) |
N3—C7—C8—N6 | −34.7 (4) | C9—N6—C8—N5 | −0.4 (4) |
N4—C7—C8—N5 | −32.3 (4) | C9—N6—C8—C7 | 174.6 (2) |
N4—C7—C8—N6 | 152.1 (3) | C9—C10—C11—N5 | −1.2 (5) |
N4—C12—C13—C14 | 176.4 (2) | C11—N5—C8—N6 | −0.3 (4) |
N4—C12—C17—C16 | −177.0 (2) | C11—N5—C8—C7 | −175.3 (2) |
N6—C9—C10—C11 | 0.5 (5) | C12—N4—C6—N2 | −164.1 (2) |
C1—N1—C5—C4 | −0.6 (5) | C12—N4—C6—C5 | 19.3 (4) |
C1—N1—C5—C6 | 175.3 (3) | C12—N4—C7—N3 | 164.2 (2) |
C1—C2—C3—C4 | 0.1 (6) | C12—N4—C7—C8 | −21.9 (4) |
C2—C3—C4—C5 | −0.5 (5) | C12—C13—C14—C15 | 0.1 (4) |
C3—C4—C5—N1 | 0.8 (5) | C13—C12—C17—C16 | 0.4 (4) |
C3—C4—C5—C6 | −174.9 (3) | C13—C14—C15—C16 | 1.1 (4) |
C4—C5—C6—N2 | 33.3 (4) | C13—C14—C15—C18 | −179.7 (3) |
C4—C5—C6—N4 | −150.5 (3) | C14—C15—C16—C17 | −1.6 (4) |
C5—N1—C1—C2 | 0.2 (6) | C15—C16—C17—C12 | 0.9 (4) |
C6—N2—N3—C7 | 0.5 (3) | C17—C12—C13—C14 | −0.8 (4) |
C6—N4—C7—N3 | 0.3 (3) | C18—C15—C16—C17 | 179.2 (3) |
C6—N4—C7—C8 | 174.2 (2) |
C17H12N6 | Dx = 1.310 Mg m−3 |
Mr = 300.33 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 1290 reflections |
a = 8.5626 (16) Å | θ = 2.2–16.6° |
b = 18.701 (4) Å | µ = 0.08 mm−1 |
c = 19.024 (4) Å | T = 293 K |
V = 3046.3 (10) Å3 | Block, clear light colourless |
Z = 8 | 0.17 × 0.14 × 0.11 mm |
F(000) = 1248 |
Bruker APEXII CCD area detector diffractometer | 1346 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.106 |
phi and ω scans | θmax = 25.1°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −9→10 |
Tmin = 0.986, Tmax = 0.991 | k = −22→22 |
20705 measured reflections | l = −22→22 |
2701 independent reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.050 | w = 1/[σ2(Fo2) + (0.0664P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.135 | (Δ/σ)max < 0.001 |
S = 0.92 | Δρmax = 0.19 e Å−3 |
2701 reflections | Δρmin = −0.17 e Å−3 |
209 parameters | Extinction correction: SHELXL (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
3 restraints | Extinction coefficient: 0.0045 (7) |
Primary atom site location: dual |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.2611 (3) | 0.63964 (12) | 0.80798 (11) | 0.0609 (6) | |
N2 | 0.3929 (3) | 0.75741 (11) | 0.67566 (12) | 0.0654 (7) | |
N3 | 0.3770 (3) | 0.74752 (12) | 0.60376 (12) | 0.0685 (7) | |
N4 | 0.3426 (2) | 0.64382 (10) | 0.65638 (10) | 0.0469 (5) | |
N5 | 0.4212 (3) | 0.59210 (13) | 0.50840 (11) | 0.0711 (7) | |
N6 | 0.2171 (3) | 0.67474 (12) | 0.48277 (13) | 0.0679 (7) | |
C1 | 0.2554 (4) | 0.63366 (17) | 0.87791 (15) | 0.0722 (9) | |
H1 | 0.183476 | 0.601986 | 0.897180 | 0.087* | |
C2 | 0.3495 (4) | 0.67147 (18) | 0.92307 (15) | 0.0815 (9) | |
H2 | 0.341471 | 0.665512 | 0.971466 | 0.098* | |
C3 | 0.4558 (4) | 0.71830 (17) | 0.89478 (16) | 0.0823 (9) | |
H3 | 0.521022 | 0.744796 | 0.923915 | 0.099* | |
C4 | 0.4648 (3) | 0.72564 (14) | 0.82340 (15) | 0.0622 (7) | |
H4 | 0.535822 | 0.757127 | 0.803127 | 0.075* | |
C5 | 0.3672 (3) | 0.68566 (13) | 0.78268 (13) | 0.0511 (7) | |
C6 | 0.3706 (3) | 0.69515 (13) | 0.70601 (14) | 0.0515 (7) | |
C7 | 0.3485 (3) | 0.67978 (14) | 0.59342 (14) | 0.0533 (7) | |
C8 | 0.3275 (3) | 0.64661 (14) | 0.52365 (14) | 0.0547 (7) | |
C9 | 0.2008 (3) | 0.64351 (18) | 0.41862 (17) | 0.0755 (9) | |
H9 | 0.126224 | 0.661370 | 0.387743 | 0.091* | |
C10 | 0.2900 (4) | 0.58703 (18) | 0.39810 (16) | 0.0789 (9) | |
H10 | 0.277146 | 0.565705 | 0.354317 | 0.095* | |
C11 | 0.3995 (4) | 0.56308 (17) | 0.44497 (16) | 0.0830 (10) | |
H11 | 0.461945 | 0.524606 | 0.431979 | 0.100* | |
C12 | 0.3166 (3) | 0.56847 (13) | 0.66557 (12) | 0.0481 (6) | |
C13 | 0.1898 (3) | 0.53672 (17) | 0.63395 (15) | 0.0664 (8) | |
H13 | 0.118539 | 0.563968 | 0.608585 | 0.080* | |
C14 | 0.1701 (4) | 0.46387 (19) | 0.64046 (19) | 0.0875 (10) | |
H14 | 0.087278 | 0.441638 | 0.617643 | 0.105* | |
C15 | 0.2707 (5) | 0.42387 (17) | 0.67999 (19) | 0.0864 (11) | |
H15 | 0.254380 | 0.374995 | 0.685170 | 0.104* | |
C16 | 0.3957 (4) | 0.45597 (15) | 0.71197 (15) | 0.0709 (8) | |
H16 | 0.464375 | 0.428659 | 0.738702 | 0.085* | |
C17 | 0.4207 (3) | 0.52890 (13) | 0.70480 (13) | 0.0538 (7) | |
H17 | 0.506161 | 0.550692 | 0.726071 | 0.065* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0576 (15) | 0.0683 (15) | 0.0567 (15) | −0.0007 (12) | 0.0050 (12) | −0.0074 (12) |
N2 | 0.0728 (17) | 0.0475 (14) | 0.0759 (17) | −0.0059 (12) | 0.0065 (13) | −0.0048 (12) |
N3 | 0.0804 (18) | 0.0537 (15) | 0.0715 (17) | 0.0008 (13) | 0.0105 (14) | 0.0004 (12) |
N4 | 0.0465 (13) | 0.0436 (12) | 0.0506 (13) | −0.0029 (10) | 0.0025 (9) | −0.0021 (10) |
N5 | 0.0746 (18) | 0.0815 (18) | 0.0571 (15) | 0.0256 (14) | −0.0045 (13) | −0.0079 (13) |
N6 | 0.0593 (16) | 0.0728 (17) | 0.0715 (17) | 0.0032 (12) | 0.0031 (13) | 0.0074 (14) |
C1 | 0.074 (2) | 0.086 (2) | 0.0561 (19) | 0.0075 (17) | 0.0065 (16) | −0.0054 (16) |
C2 | 0.088 (3) | 0.102 (3) | 0.0541 (18) | 0.0295 (17) | −0.0038 (16) | −0.0119 (16) |
C3 | 0.071 (2) | 0.095 (2) | 0.0809 (15) | 0.0189 (15) | −0.0160 (16) | −0.0311 (18) |
C4 | 0.0452 (16) | 0.0584 (16) | 0.0831 (15) | 0.0007 (14) | −0.0038 (14) | −0.0199 (15) |
C5 | 0.0432 (16) | 0.0506 (16) | 0.0595 (16) | 0.0049 (14) | −0.0008 (13) | −0.0107 (13) |
C6 | 0.0464 (16) | 0.0452 (16) | 0.0628 (17) | −0.0034 (13) | 0.0036 (13) | −0.0069 (14) |
C7 | 0.0492 (17) | 0.0521 (17) | 0.0587 (17) | 0.0058 (13) | 0.0053 (13) | 0.0045 (14) |
C8 | 0.0521 (17) | 0.0583 (17) | 0.0537 (17) | 0.0037 (15) | 0.0046 (14) | 0.0052 (14) |
C9 | 0.064 (2) | 0.090 (2) | 0.073 (2) | −0.0006 (18) | −0.0077 (17) | 0.0113 (18) |
C10 | 0.075 (2) | 0.105 (3) | 0.0564 (19) | 0.0201 (19) | −0.0064 (16) | −0.0113 (18) |
C11 | 0.088 (2) | 0.097 (2) | 0.063 (2) | 0.032 (2) | −0.0099 (19) | −0.0135 (18) |
C12 | 0.0486 (16) | 0.0479 (16) | 0.0479 (15) | −0.0063 (13) | 0.0044 (13) | −0.0027 (13) |
C13 | 0.0558 (19) | 0.071 (2) | 0.0724 (19) | −0.0126 (16) | −0.0048 (15) | −0.0079 (15) |
C14 | 0.083 (3) | 0.072 (2) | 0.108 (3) | −0.036 (2) | 0.002 (2) | −0.019 (2) |
C15 | 0.104 (3) | 0.0479 (19) | 0.107 (3) | −0.017 (2) | 0.023 (2) | −0.0058 (19) |
C16 | 0.081 (2) | 0.0552 (19) | 0.076 (2) | 0.0013 (18) | 0.0086 (18) | 0.0041 (15) |
C17 | 0.0573 (18) | 0.0505 (16) | 0.0537 (16) | −0.0038 (13) | 0.0044 (14) | −0.0012 (13) |
N1—C1 | 1.336 (3) | C4—C5 | 1.363 (3) |
N1—C5 | 1.341 (3) | C5—C6 | 1.470 (3) |
N2—N3 | 1.387 (3) | C7—C8 | 1.476 (3) |
N2—C6 | 1.314 (3) | C9—H9 | 0.9300 |
N3—C7 | 1.305 (3) | C9—C10 | 1.360 (4) |
N4—C6 | 1.368 (3) | C10—H10 | 0.9300 |
N4—C7 | 1.375 (3) | C10—C11 | 1.369 (4) |
N4—C12 | 1.437 (3) | C11—H11 | 0.9300 |
N5—C8 | 1.329 (3) | C12—C13 | 1.376 (3) |
N5—C11 | 1.336 (3) | C12—C17 | 1.378 (3) |
N6—C8 | 1.332 (3) | C13—H13 | 0.9300 |
N6—C9 | 1.360 (3) | C13—C14 | 1.378 (4) |
C1—H1 | 0.9300 | C14—H14 | 0.9300 |
C1—C2 | 1.374 (4) | C14—C15 | 1.366 (5) |
C2—H2 | 0.9300 | C15—H15 | 0.9300 |
C2—C3 | 1.373 (4) | C15—C16 | 1.370 (4) |
C3—H3 | 0.9300 | C16—H16 | 0.9300 |
C3—C4 | 1.367 (4) | C16—C17 | 1.387 (3) |
C4—H4 | 0.9300 | C17—H17 | 0.9300 |
C1—N1—C5 | 115.8 (2) | N5—C8—C7 | 116.4 (2) |
C6—N2—N3 | 107.5 (2) | N6—C8—C7 | 116.4 (2) |
C7—N3—N2 | 107.3 (2) | N6—C9—H9 | 118.9 |
C6—N4—C7 | 104.6 (2) | N6—C9—C10 | 122.2 (3) |
C6—N4—C12 | 129.2 (2) | C10—C9—H9 | 118.9 |
C7—N4—C12 | 126.2 (2) | C9—C10—H10 | 121.6 |
C8—N5—C11 | 115.1 (2) | C9—C10—C11 | 116.8 (3) |
C8—N6—C9 | 115.3 (2) | C11—C10—H10 | 121.6 |
N1—C1—H1 | 118.0 | N5—C11—C10 | 123.4 (3) |
N1—C1—C2 | 123.9 (3) | N5—C11—H11 | 118.3 |
C2—C1—H1 | 118.0 | C10—C11—H11 | 118.3 |
C1—C2—H2 | 120.9 | C13—C12—N4 | 119.5 (2) |
C3—C2—C1 | 118.2 (3) | C13—C12—C17 | 121.0 (2) |
C3—C2—H2 | 120.9 | C17—C12—N4 | 119.4 (2) |
C2—C3—H3 | 120.3 | C12—C13—H13 | 120.5 |
C4—C3—C2 | 119.4 (3) | C12—C13—C14 | 118.9 (3) |
C4—C3—H3 | 120.3 | C14—C13—H13 | 120.5 |
C3—C4—H4 | 120.8 | C13—C14—H14 | 119.5 |
C5—C4—C3 | 118.3 (3) | C15—C14—C13 | 120.9 (3) |
C5—C4—H4 | 120.8 | C15—C14—H14 | 119.5 |
N1—C5—C4 | 124.3 (3) | C14—C15—H15 | 120.1 |
N1—C5—C6 | 116.5 (2) | C14—C15—C16 | 119.8 (3) |
C4—C5—C6 | 119.1 (3) | C16—C15—H15 | 120.1 |
N2—C6—N4 | 110.1 (2) | C15—C16—H16 | 119.7 |
N2—C6—C5 | 123.1 (2) | C15—C16—C17 | 120.5 (3) |
N4—C6—C5 | 126.7 (2) | C17—C16—H16 | 119.7 |
N3—C7—N4 | 110.5 (2) | C12—C17—C16 | 118.8 (3) |
N3—C7—C8 | 124.5 (2) | C12—C17—H17 | 120.6 |
N4—C7—C8 | 125.0 (2) | C16—C17—H17 | 120.6 |
N5—C8—N6 | 127.1 (3) | ||
N1—C1—C2—C3 | 0.0 (5) | C6—N4—C7—C8 | 179.0 (2) |
N1—C5—C6—N2 | 140.9 (3) | C6—N4—C12—C13 | 129.8 (3) |
N1—C5—C6—N4 | −35.0 (4) | C6—N4—C12—C17 | −51.5 (3) |
N2—N3—C7—N4 | 0.8 (3) | C7—N4—C6—N2 | −0.4 (3) |
N2—N3—C7—C8 | −178.5 (2) | C7—N4—C6—C5 | 175.8 (2) |
N3—N2—C6—N4 | 1.0 (3) | C7—N4—C12—C13 | −52.0 (3) |
N3—N2—C6—C5 | −175.5 (2) | C7—N4—C12—C17 | 126.7 (3) |
N3—C7—C8—N5 | 124.0 (3) | C8—N5—C11—C10 | 0.3 (5) |
N3—C7—C8—N6 | −55.8 (4) | C8—N6—C9—C10 | 0.7 (4) |
N4—C7—C8—N5 | −55.2 (3) | C9—N6—C8—N5 | −0.1 (4) |
N4—C7—C8—N6 | 125.0 (3) | C9—N6—C8—C7 | 179.6 (2) |
N4—C12—C13—C14 | 177.0 (2) | C9—C10—C11—N5 | 0.2 (5) |
N4—C12—C17—C16 | −178.7 (2) | C11—N5—C8—N6 | −0.4 (4) |
N6—C9—C10—C11 | −0.7 (5) | C11—N5—C8—C7 | 179.9 (2) |
C1—N1—C5—C4 | −0.7 (4) | C12—N4—C6—N2 | 178.1 (2) |
C1—N1—C5—C6 | −177.5 (2) | C12—N4—C6—C5 | −5.7 (4) |
C1—C2—C3—C4 | −0.2 (4) | C12—N4—C7—N3 | −178.8 (2) |
C2—C3—C4—C5 | −0.1 (4) | C12—N4—C7—C8 | 0.5 (4) |
C3—C4—C5—N1 | 0.6 (4) | C12—C13—C14—C15 | 2.7 (5) |
C3—C4—C5—C6 | 177.4 (2) | C13—C12—C17—C16 | 0.0 (4) |
C4—C5—C6—N2 | −36.2 (4) | C13—C14—C15—C16 | −2.0 (5) |
C4—C5—C6—N4 | 148.0 (2) | C14—C15—C16—C17 | 0.3 (5) |
C5—N1—C1—C2 | 0.4 (4) | C15—C16—C17—C12 | 0.7 (4) |
C6—N2—N3—C7 | −1.1 (3) | C17—C12—C13—C14 | −1.7 (4) |
C6—N4—C7—N3 | −0.3 (3) |
C17H11BrN6 | Z = 2 |
Mr = 379.23 | F(000) = 380 |
Triclinic, P1 | Dx = 1.574 Mg m−3 |
a = 8.5510 (13) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.4214 (15) Å | Cell parameters from 2667 reflections |
c = 11.5813 (18) Å | θ = 2.4–26.1° |
α = 85.894 (2)° | µ = 2.58 mm−1 |
β = 70.776 (2)° | T = 293 K |
γ = 65.640 (2)° | Block, clear light colourless |
V = 800.3 (2) Å3 | 0.19 × 0.16 × 0.12 mm |
Bruker APEXII CCD area detector diffractometer | 2264 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
phi and ω scans | θmax = 25.1°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −10→10 |
Tmin = 0.619, Tmax = 0.734 | k = −11→11 |
5827 measured reflections | l = −13→13 |
2813 independent reflections |
Refinement on F2 | 42 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.101 | w = 1/[σ2(Fo2) + (0.0343P)2 + 0.7585P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
2813 reflections | Δρmax = 0.73 e Å−3 |
217 parameters | Δρmin = −0.53 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
Br1 | 1.27151 (5) | 0.65581 (6) | 0.58278 (4) | 0.07508 (19) | |
N1 | 0.4324 (4) | 0.9672 (3) | 0.6896 (3) | 0.0628 (8) | |
N2 | 0.2244 (3) | 0.7508 (3) | 0.8981 (3) | 0.0520 (7) | |
N3 | 0.2992 (3) | 0.5913 (3) | 0.9065 (2) | 0.0493 (7) | |
N4 | 0.5182 (3) | 0.6601 (3) | 0.7952 (2) | 0.0352 (5) | |
N5 | 0.7600 (4) | 0.3286 (3) | 0.7388 (3) | 0.0595 (8) | |
N6 | 0.5368 (4) | 0.2789 (4) | 0.9008 (3) | 0.0597 (8) | |
C1 | 0.4071 (6) | 1.1130 (5) | 0.6604 (4) | 0.0787 (13) | |
H1 | 0.479963 | 1.126790 | 0.584641 | 0.094* | |
C2 | 0.2789 (6) | 1.2443 (5) | 0.7363 (5) | 0.0808 (13) | |
H2 | 0.266611 | 1.343748 | 0.712749 | 0.097* | |
C3 | 0.1713 (6) | 1.2240 (5) | 0.8460 (4) | 0.0804 (13) | |
H3 | 0.081477 | 1.310378 | 0.898076 | 0.096* | |
C4 | 0.1950 (5) | 1.0760 (4) | 0.8804 (3) | 0.0610 (10) | |
H4 | 0.123224 | 1.060289 | 0.955799 | 0.073* | |
C5 | 0.3291 (4) | 0.9502 (4) | 0.7993 (3) | 0.0461 (8) | |
C6 | 0.3560 (4) | 0.7900 (4) | 0.8317 (3) | 0.0418 (7) | |
C7 | 0.4746 (4) | 0.5384 (4) | 0.8451 (3) | 0.0390 (7) | |
C8 | 0.5994 (4) | 0.3724 (4) | 0.8267 (3) | 0.0400 (7) | |
C9 | 0.6466 (6) | 0.1271 (5) | 0.8801 (4) | 0.0752 (12) | |
H9 | 0.606912 | 0.057322 | 0.928239 | 0.090* | |
C10 | 0.8138 (7) | 0.0686 (4) | 0.7920 (4) | 0.0769 (12) | |
H10 | 0.887981 | −0.037842 | 0.779115 | 0.092* | |
C11 | 0.8660 (6) | 0.1761 (4) | 0.7238 (4) | 0.0768 (12) | |
H11 | 0.980552 | 0.141022 | 0.664281 | 0.092* | |
C12 | 0.6983 (3) | 0.6579 (3) | 0.7434 (3) | 0.0337 (6) | |
C13 | 0.7943 (4) | 0.6467 (3) | 0.8207 (3) | 0.0370 (6) | |
H13 | 0.744552 | 0.639134 | 0.904150 | 0.044* | |
C14 | 0.9656 (4) | 0.6466 (3) | 0.7735 (3) | 0.0421 (7) | |
H14 | 1.032378 | 0.639405 | 0.824585 | 0.050* | |
C15 | 1.0353 (4) | 0.6575 (4) | 0.6491 (3) | 0.0529 (6) | |
C16 | 0.9405 (4) | 0.6665 (4) | 0.5715 (3) | 0.0459 (7) | |
H16 | 0.991259 | 0.671997 | 0.487854 | 0.055* | |
C17 | 0.7694 (4) | 0.6673 (3) | 0.6186 (3) | 0.0407 (7) | |
H17 | 0.703110 | 0.674001 | 0.567279 | 0.049* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0427 (2) | 0.1164 (4) | 0.0665 (3) | −0.0476 (2) | 0.00220 (17) | −0.0005 (2) |
N1 | 0.0529 (17) | 0.0464 (17) | 0.0630 (19) | −0.0077 (13) | −0.0040 (15) | 0.0056 (14) |
N2 | 0.0300 (13) | 0.0641 (19) | 0.0564 (17) | −0.0192 (13) | −0.0065 (12) | −0.0007 (14) |
N3 | 0.0376 (14) | 0.0654 (19) | 0.0476 (15) | −0.0287 (13) | −0.0075 (12) | 0.0036 (13) |
N4 | 0.0268 (11) | 0.0404 (13) | 0.0367 (13) | −0.0148 (10) | −0.0072 (10) | 0.0034 (10) |
N5 | 0.0580 (17) | 0.0383 (16) | 0.0620 (18) | −0.0166 (13) | 0.0005 (14) | 0.0050 (13) |
N6 | 0.0668 (19) | 0.0611 (19) | 0.0567 (18) | −0.0386 (16) | −0.0140 (15) | 0.0175 (14) |
C1 | 0.071 (3) | 0.052 (2) | 0.081 (3) | −0.009 (2) | −0.008 (2) | 0.018 (2) |
C2 | 0.082 (3) | 0.045 (2) | 0.093 (3) | −0.008 (2) | −0.027 (3) | 0.011 (2) |
C3 | 0.071 (3) | 0.054 (2) | 0.084 (3) | 0.004 (2) | −0.020 (2) | −0.013 (2) |
C4 | 0.0468 (19) | 0.058 (2) | 0.056 (2) | −0.0051 (16) | −0.0084 (16) | −0.0042 (17) |
C5 | 0.0298 (15) | 0.0451 (18) | 0.0528 (19) | −0.0064 (13) | −0.0116 (14) | −0.0010 (15) |
C6 | 0.0269 (14) | 0.0490 (18) | 0.0427 (17) | −0.0117 (13) | −0.0066 (12) | −0.0049 (14) |
C7 | 0.0361 (15) | 0.0527 (18) | 0.0346 (15) | −0.0258 (14) | −0.0106 (12) | 0.0062 (13) |
C8 | 0.0442 (16) | 0.0481 (18) | 0.0362 (16) | −0.0274 (14) | −0.0135 (13) | 0.0055 (13) |
C9 | 0.096 (3) | 0.066 (3) | 0.077 (3) | −0.051 (3) | −0.025 (3) | 0.029 (2) |
C10 | 0.102 (3) | 0.041 (2) | 0.080 (3) | −0.030 (2) | −0.022 (3) | 0.0097 (19) |
C11 | 0.076 (3) | 0.049 (2) | 0.073 (3) | −0.0188 (19) | 0.007 (2) | 0.0035 (19) |
C12 | 0.0274 (12) | 0.0310 (13) | 0.0391 (14) | −0.0129 (10) | −0.0053 (11) | 0.0021 (11) |
C13 | 0.0326 (13) | 0.0396 (14) | 0.0348 (14) | −0.0160 (11) | −0.0049 (11) | 0.0032 (11) |
C14 | 0.0329 (13) | 0.0486 (16) | 0.0464 (16) | −0.0200 (12) | −0.0107 (12) | 0.0016 (13) |
C15 | 0.0381 (9) | 0.0694 (10) | 0.0577 (10) | −0.0385 (8) | −0.0017 (9) | −0.0003 (9) |
C16 | 0.0404 (15) | 0.0497 (16) | 0.0393 (15) | −0.0206 (13) | −0.0002 (12) | 0.0021 (13) |
C17 | 0.0354 (14) | 0.0467 (16) | 0.0352 (14) | −0.0151 (12) | −0.0080 (11) | 0.0019 (12) |
Br1—C15 | 1.903 (3) | C4—H4 | 0.9300 |
N1—C1 | 1.336 (5) | C4—C5 | 1.389 (5) |
N1—C5 | 1.330 (4) | C5—C6 | 1.471 (5) |
N2—N3 | 1.380 (4) | C7—C8 | 1.466 (4) |
N2—C6 | 1.314 (4) | C9—H9 | 0.9300 |
N3—C7 | 1.317 (4) | C9—C10 | 1.363 (6) |
N4—C6 | 1.374 (4) | C10—H10 | 0.9300 |
N4—C7 | 1.381 (4) | C10—C11 | 1.369 (5) |
N4—C12 | 1.448 (3) | C11—H11 | 0.9300 |
N5—C8 | 1.329 (4) | C12—C13 | 1.373 (4) |
N5—C11 | 1.332 (5) | C12—C17 | 1.384 (4) |
N6—C8 | 1.333 (4) | C13—H13 | 0.9300 |
N6—C9 | 1.333 (5) | C13—C14 | 1.385 (4) |
C1—H1 | 0.9300 | C14—H14 | 0.9300 |
C1—C2 | 1.381 (6) | C14—C15 | 1.381 (4) |
C2—H2 | 0.9300 | C15—C16 | 1.372 (5) |
C2—C3 | 1.356 (6) | C16—H16 | 0.9300 |
C3—H3 | 0.9300 | C16—C17 | 1.380 (4) |
C3—C4 | 1.373 (6) | C17—H17 | 0.9300 |
C5—N1—C1 | 117.1 (3) | N5—C8—C7 | 118.4 (3) |
C6—N2—N3 | 107.6 (2) | N6—C8—C7 | 115.4 (3) |
C7—N3—N2 | 107.6 (2) | N6—C9—H9 | 118.2 |
C6—N4—C7 | 104.4 (2) | N6—C9—C10 | 123.5 (3) |
C6—N4—C12 | 126.8 (2) | C10—C9—H9 | 118.2 |
C7—N4—C12 | 127.1 (2) | C9—C10—H10 | 122.0 |
C8—N5—C11 | 115.9 (3) | C9—C10—C11 | 116.0 (4) |
C9—N6—C8 | 115.4 (3) | C11—C10—H10 | 122.0 |
N1—C1—H1 | 118.2 | N5—C11—C10 | 123.0 (4) |
N1—C1—C2 | 123.7 (4) | N5—C11—H11 | 118.5 |
C2—C1—H1 | 118.2 | C10—C11—H11 | 118.5 |
C1—C2—H2 | 120.9 | C13—C12—N4 | 118.5 (2) |
C3—C2—C1 | 118.1 (4) | C13—C12—C17 | 121.6 (3) |
C3—C2—H2 | 120.9 | C17—C12—N4 | 119.9 (3) |
C2—C3—H3 | 120.0 | C12—C13—H13 | 120.2 |
C2—C3—C4 | 120.0 (4) | C12—C13—C14 | 119.6 (3) |
C4—C3—H3 | 120.0 | C14—C13—H13 | 120.2 |
C3—C4—H4 | 120.9 | C13—C14—H14 | 120.7 |
C3—C4—C5 | 118.2 (4) | C15—C14—C13 | 118.6 (3) |
C5—C4—H4 | 120.9 | C15—C14—H14 | 120.7 |
N1—C5—C4 | 122.9 (3) | C14—C15—Br1 | 119.1 (3) |
N1—C5—C6 | 117.2 (3) | C16—C15—Br1 | 119.1 (2) |
C4—C5—C6 | 119.8 (3) | C16—C15—C14 | 121.8 (3) |
N2—C6—N4 | 110.3 (3) | C15—C16—H16 | 120.2 |
N2—C6—C5 | 123.9 (3) | C15—C16—C17 | 119.6 (3) |
N4—C6—C5 | 125.7 (3) | C17—C16—H16 | 120.2 |
N3—C7—N4 | 110.0 (3) | C12—C17—H17 | 120.6 |
N3—C7—C8 | 123.9 (3) | C16—C17—C12 | 118.8 (3) |
N4—C7—C8 | 126.0 (2) | C16—C17—H17 | 120.6 |
N5—C8—N6 | 126.2 (3) | ||
Br1—C15—C16—C17 | 179.8 (2) | C6—N4—C7—C8 | 176.2 (3) |
N1—C1—C2—C3 | −0.8 (8) | C6—N4—C12—C13 | 94.1 (3) |
N1—C5—C6—N2 | −144.9 (3) | C6—N4—C12—C17 | −85.8 (4) |
N1—C5—C6—N4 | 33.1 (5) | C7—N4—C6—N2 | −0.2 (3) |
N2—N3—C7—N4 | −0.3 (3) | C7—N4—C6—C5 | −178.4 (3) |
N2—N3—C7—C8 | −176.3 (3) | C7—N4—C12—C13 | −69.0 (4) |
N3—N2—C6—N4 | 0.0 (3) | C7—N4—C12—C17 | 111.1 (3) |
N3—N2—C6—C5 | 178.3 (3) | C8—N5—C11—C10 | 1.4 (7) |
N3—C7—C8—N5 | 162.8 (3) | C8—N6—C9—C10 | 1.6 (6) |
N3—C7—C8—N6 | −16.2 (4) | C9—N6—C8—N5 | −2.1 (5) |
N4—C7—C8—N5 | −12.6 (5) | C9—N6—C8—C7 | 176.8 (3) |
N4—C7—C8—N6 | 168.4 (3) | C9—C10—C11—N5 | −1.7 (7) |
N4—C12—C13—C14 | −179.1 (2) | C11—N5—C8—N6 | 0.6 (5) |
N4—C12—C17—C16 | 179.4 (3) | C11—N5—C8—C7 | −178.2 (3) |
N6—C9—C10—C11 | 0.1 (7) | C12—N4—C6—N2 | −166.3 (3) |
C1—N1—C5—C4 | 2.4 (6) | C12—N4—C6—C5 | 15.4 (5) |
C1—N1—C5—C6 | 179.7 (3) | C12—N4—C7—N3 | 166.3 (3) |
C1—C2—C3—C4 | 1.8 (7) | C12—N4—C7—C8 | −17.8 (4) |
C2—C3—C4—C5 | −0.8 (7) | C12—C13—C14—C15 | −0.2 (4) |
C3—C4—C5—N1 | −1.4 (6) | C13—C12—C17—C16 | −0.5 (4) |
C3—C4—C5—C6 | −178.7 (3) | C13—C14—C15—Br1 | −179.5 (2) |
C4—C5—C6—N2 | 32.5 (5) | C13—C14—C15—C16 | −0.7 (5) |
C4—C5—C6—N4 | −149.4 (3) | C14—C15—C16—C17 | 1.0 (5) |
C5—N1—C1—C2 | −1.3 (7) | C15—C16—C17—C12 | −0.4 (4) |
C6—N2—N3—C7 | 0.2 (3) | C17—C12—C13—C14 | 0.8 (4) |
C6—N4—C7—N3 | 0.3 (3) |
C17H11ClN6 | Z = 2 |
Mr = 334.77 | F(000) = 344 |
Triclinic, P1 | Dx = 1.407 Mg m−3 |
a = 8.5105 (13) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.3681 (14) Å | Cell parameters from 3029 reflections |
c = 10.8959 (16) Å | θ = 2.6–26.5° |
α = 81.355 (2)° | µ = 0.25 mm−1 |
β = 82.482 (2)° | T = 293 K |
γ = 67.388 (2)° | Block, clear light colourless |
V = 790.3 (2) Å3 | 0.18 × 0.17 × 0.14 mm |
Bruker APEXII CCD area detector diffractometer | 2383 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
phi and ω scans | θmax = 25.1°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −9→10 |
Tmin = 0.955, Tmax = 0.965 | k = −11→11 |
5712 measured reflections | l = −12→12 |
2765 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.102 | w = 1/[σ2(Fo2) + (0.0432P)2 + 0.253P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
2765 reflections | Δρmax = 0.17 e Å−3 |
217 parameters | Δρmin = −0.22 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 1.00724 (6) | 0.66378 (7) | 0.40056 (5) | 0.06079 (19) | |
N1 | 0.2531 (2) | 0.9522 (2) | 0.30700 (17) | 0.0638 (5) | |
N2 | 0.17141 (19) | 0.7360 (2) | 0.09767 (15) | 0.0519 (4) | |
N3 | 0.2479 (2) | 0.5775 (2) | 0.09445 (15) | 0.0522 (4) | |
N4 | 0.39452 (17) | 0.64924 (16) | 0.20889 (13) | 0.0376 (3) | |
N5 | 0.5750 (3) | 0.3255 (2) | 0.29005 (17) | 0.0646 (5) | |
N6 | 0.4922 (3) | 0.2676 (2) | 0.10816 (17) | 0.0665 (5) | |
C1 | 0.2042 (4) | 1.0970 (3) | 0.3366 (2) | 0.0814 (8) | |
H1 | 0.232181 | 1.110408 | 0.412588 | 0.098* | |
C2 | 0.1149 (3) | 1.2277 (3) | 0.2616 (3) | 0.0796 (7) | |
H2 | 0.083816 | 1.326243 | 0.286470 | 0.096* | |
C3 | 0.0735 (3) | 1.2096 (3) | 0.1510 (2) | 0.0765 (7) | |
H3 | 0.012383 | 1.295962 | 0.098710 | 0.092* | |
C4 | 0.1226 (3) | 1.0620 (3) | 0.1161 (2) | 0.0616 (6) | |
H4 | 0.096085 | 1.047237 | 0.040053 | 0.074* | |
C5 | 0.2118 (2) | 0.9370 (2) | 0.19654 (18) | 0.0463 (4) | |
C6 | 0.2602 (2) | 0.7767 (2) | 0.16599 (16) | 0.0421 (4) | |
C7 | 0.3809 (2) | 0.5276 (2) | 0.16051 (16) | 0.0416 (4) | |
C8 | 0.4915 (2) | 0.3633 (2) | 0.18782 (17) | 0.0456 (4) | |
C9 | 0.5897 (4) | 0.1186 (3) | 0.1370 (3) | 0.0863 (8) | |
H9 | 0.593537 | 0.046315 | 0.085612 | 0.104* | |
C10 | 0.6844 (4) | 0.0668 (3) | 0.2380 (3) | 0.0933 (9) | |
H10 | 0.753036 | −0.037510 | 0.254984 | 0.112* | |
C11 | 0.6733 (4) | 0.1761 (3) | 0.3136 (3) | 0.0886 (8) | |
H11 | 0.736249 | 0.144766 | 0.383099 | 0.106* | |
C12 | 0.5441 (2) | 0.64901 (18) | 0.25914 (15) | 0.0352 (4) | |
C13 | 0.5468 (2) | 0.6525 (2) | 0.38479 (16) | 0.0423 (4) | |
H13 | 0.452750 | 0.653274 | 0.439250 | 0.051* | |
C14 | 0.6907 (2) | 0.6547 (2) | 0.42902 (16) | 0.0445 (4) | |
H14 | 0.694864 | 0.657181 | 0.513504 | 0.053* | |
C15 | 0.8283 (2) | 0.6531 (2) | 0.34571 (16) | 0.0400 (4) | |
C16 | 0.8273 (2) | 0.6466 (2) | 0.22091 (17) | 0.0443 (4) | |
H16 | 0.922184 | 0.643682 | 0.166676 | 0.053* | |
C17 | 0.6831 (2) | 0.6444 (2) | 0.17696 (16) | 0.0417 (4) | |
H17 | 0.679923 | 0.639756 | 0.092688 | 0.050* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0501 (3) | 0.0850 (4) | 0.0577 (3) | −0.0339 (3) | −0.0209 (2) | −0.0005 (3) |
N1 | 0.0710 (12) | 0.0497 (10) | 0.0616 (11) | −0.0055 (9) | −0.0249 (9) | −0.0084 (8) |
N2 | 0.0412 (9) | 0.0643 (11) | 0.0537 (10) | −0.0217 (8) | −0.0122 (7) | −0.0042 (8) |
N3 | 0.0477 (9) | 0.0712 (11) | 0.0504 (9) | −0.0333 (8) | −0.0080 (7) | −0.0105 (8) |
N4 | 0.0330 (7) | 0.0431 (8) | 0.0391 (8) | −0.0156 (6) | −0.0055 (6) | −0.0058 (6) |
N5 | 0.0837 (13) | 0.0436 (10) | 0.0632 (11) | −0.0177 (9) | −0.0148 (10) | −0.0045 (8) |
N6 | 0.0839 (13) | 0.0626 (12) | 0.0634 (11) | −0.0359 (10) | 0.0041 (10) | −0.0232 (9) |
C1 | 0.101 (2) | 0.0564 (14) | 0.0742 (16) | −0.0038 (13) | −0.0302 (14) | −0.0179 (12) |
C2 | 0.0843 (18) | 0.0530 (14) | 0.0854 (18) | −0.0039 (12) | −0.0153 (14) | −0.0110 (12) |
C3 | 0.0712 (15) | 0.0574 (14) | 0.0769 (17) | −0.0002 (12) | −0.0149 (13) | 0.0074 (12) |
C4 | 0.0539 (12) | 0.0676 (14) | 0.0529 (12) | −0.0102 (10) | −0.0164 (10) | 0.0012 (10) |
C5 | 0.0352 (9) | 0.0501 (11) | 0.0493 (10) | −0.0111 (8) | −0.0067 (8) | −0.0027 (8) |
C6 | 0.0325 (9) | 0.0534 (11) | 0.0397 (9) | −0.0158 (8) | −0.0072 (7) | −0.0001 (8) |
C7 | 0.0412 (9) | 0.0513 (10) | 0.0400 (9) | −0.0250 (8) | −0.0001 (7) | −0.0093 (8) |
C8 | 0.0509 (11) | 0.0507 (11) | 0.0430 (10) | −0.0284 (9) | 0.0046 (8) | −0.0101 (8) |
C9 | 0.118 (2) | 0.0662 (17) | 0.0839 (19) | −0.0437 (16) | 0.0127 (17) | −0.0289 (14) |
C10 | 0.118 (2) | 0.0407 (13) | 0.105 (2) | −0.0171 (14) | 0.0076 (19) | −0.0079 (13) |
C11 | 0.116 (2) | 0.0506 (14) | 0.0872 (19) | −0.0173 (14) | −0.0232 (17) | 0.0028 (13) |
C12 | 0.0320 (8) | 0.0336 (8) | 0.0405 (9) | −0.0113 (7) | −0.0085 (7) | −0.0036 (7) |
C13 | 0.0377 (9) | 0.0495 (10) | 0.0382 (9) | −0.0156 (8) | −0.0020 (7) | −0.0032 (7) |
C14 | 0.0460 (10) | 0.0522 (11) | 0.0355 (9) | −0.0168 (8) | −0.0110 (8) | −0.0025 (8) |
C15 | 0.0355 (9) | 0.0394 (9) | 0.0462 (10) | −0.0126 (7) | −0.0157 (7) | −0.0008 (7) |
C16 | 0.0355 (9) | 0.0541 (11) | 0.0447 (10) | −0.0182 (8) | −0.0025 (7) | −0.0058 (8) |
C17 | 0.0406 (9) | 0.0512 (10) | 0.0357 (9) | −0.0180 (8) | −0.0051 (7) | −0.0080 (7) |
Cl1—C15 | 1.7495 (16) | C4—H4 | 0.9300 |
N1—C1 | 1.334 (3) | C4—C5 | 1.377 (3) |
N1—C5 | 1.339 (3) | C5—C6 | 1.475 (3) |
N2—N3 | 1.377 (2) | C7—C8 | 1.471 (3) |
N2—C6 | 1.313 (2) | C9—H9 | 0.9300 |
N3—C7 | 1.313 (2) | C9—C10 | 1.367 (4) |
N4—C6 | 1.368 (2) | C10—H10 | 0.9300 |
N4—C7 | 1.374 (2) | C10—C11 | 1.377 (4) |
N4—C12 | 1.449 (2) | C11—H11 | 0.9300 |
N5—C8 | 1.329 (3) | C12—C13 | 1.378 (2) |
N5—C11 | 1.331 (3) | C12—C17 | 1.377 (2) |
N6—C8 | 1.336 (2) | C13—H13 | 0.9300 |
N6—C9 | 1.335 (3) | C13—C14 | 1.382 (2) |
C1—H1 | 0.9300 | C14—H14 | 0.9300 |
C1—C2 | 1.374 (3) | C14—C15 | 1.381 (3) |
C2—H2 | 0.9300 | C15—C16 | 1.372 (3) |
C2—C3 | 1.351 (4) | C16—H16 | 0.9300 |
C3—H3 | 0.9300 | C16—C17 | 1.383 (2) |
C3—C4 | 1.379 (3) | C17—H17 | 0.9300 |
C1—N1—C5 | 116.48 (18) | N5—C8—C7 | 116.99 (16) |
C6—N2—N3 | 107.51 (15) | N6—C8—C7 | 115.71 (18) |
C7—N3—N2 | 107.42 (14) | N6—C9—H9 | 118.3 |
C6—N4—C7 | 104.27 (14) | N6—C9—C10 | 123.4 (2) |
C6—N4—C12 | 126.84 (14) | C10—C9—H9 | 118.3 |
C7—N4—C12 | 126.36 (14) | C9—C10—H10 | 121.6 |
C8—N5—C11 | 116.1 (2) | C9—C10—C11 | 116.9 (2) |
C9—N6—C8 | 114.5 (2) | C11—C10—H10 | 121.6 |
N1—C1—H1 | 118.0 | N5—C11—C10 | 121.9 (3) |
N1—C1—C2 | 124.1 (2) | N5—C11—H11 | 119.1 |
C2—C1—H1 | 118.0 | C10—C11—H11 | 119.1 |
C1—C2—H2 | 120.8 | C13—C12—N4 | 120.92 (15) |
C3—C2—C1 | 118.5 (2) | C17—C12—N4 | 117.61 (14) |
C3—C2—H2 | 120.8 | C17—C12—C13 | 121.47 (15) |
C2—C3—H3 | 120.3 | C12—C13—H13 | 120.4 |
C2—C3—C4 | 119.5 (2) | C12—C13—C14 | 119.27 (16) |
C4—C3—H3 | 120.3 | C14—C13—H13 | 120.4 |
C3—C4—H4 | 120.7 | C13—C14—H14 | 120.5 |
C5—C4—C3 | 118.5 (2) | C15—C14—C13 | 118.92 (16) |
C5—C4—H4 | 120.7 | C15—C14—H14 | 120.5 |
N1—C5—C4 | 123.01 (19) | C14—C15—Cl1 | 119.00 (13) |
N1—C5—C6 | 116.42 (16) | C16—C15—Cl1 | 119.04 (14) |
C4—C5—C6 | 120.52 (18) | C16—C15—C14 | 121.95 (15) |
N2—C6—N4 | 110.45 (16) | C15—C16—H16 | 120.5 |
N2—C6—C5 | 123.32 (16) | C15—C16—C17 | 118.96 (16) |
N4—C6—C5 | 126.13 (15) | C17—C16—H16 | 120.5 |
N3—C7—N4 | 110.34 (16) | C12—C17—C16 | 119.40 (16) |
N3—C7—C8 | 124.94 (16) | C12—C17—H17 | 120.3 |
N4—C7—C8 | 124.54 (15) | C16—C17—H17 | 120.3 |
N5—C8—N6 | 127.27 (19) | ||
Cl1—C15—C16—C17 | −177.46 (14) | C6—N4—C7—C8 | −175.78 (16) |
N1—C1—C2—C3 | 0.0 (5) | C6—N4—C12—C13 | 90.6 (2) |
N1—C5—C6—N2 | 148.07 (19) | C6—N4—C12—C17 | −89.8 (2) |
N1—C5—C6—N4 | −27.9 (3) | C7—N4—C6—N2 | 0.35 (19) |
N2—N3—C7—N4 | 0.5 (2) | C7—N4—C6—C5 | 176.74 (16) |
N2—N3—C7—C8 | 175.73 (15) | C7—N4—C12—C13 | −110.35 (19) |
N3—N2—C6—N4 | −0.1 (2) | C7—N4—C12—C17 | 69.3 (2) |
N3—N2—C6—C5 | −176.59 (16) | C8—N5—C11—C10 | −1.5 (4) |
N3—C7—C8—N5 | −154.66 (19) | C8—N6—C9—C10 | −1.1 (4) |
N3—C7—C8—N6 | 23.3 (3) | C9—N6—C8—N5 | −0.5 (3) |
N4—C7—C8—N5 | 19.9 (3) | C9—N6—C8—C7 | −178.21 (19) |
N4—C7—C8—N6 | −162.08 (17) | C9—C10—C11—N5 | 0.1 (5) |
N4—C12—C13—C14 | −178.95 (16) | C11—N5—C8—N6 | 1.8 (3) |
N4—C12—C17—C16 | 178.94 (15) | C11—N5—C8—C7 | 179.5 (2) |
N6—C9—C10—C11 | 1.3 (5) | C12—N4—C6—N2 | 163.09 (15) |
C1—N1—C5—C4 | −0.5 (3) | C12—N4—C6—C5 | −20.5 (3) |
C1—N1—C5—C6 | −177.8 (2) | C12—N4—C7—N3 | −163.36 (16) |
C1—C2—C3—C4 | −0.5 (4) | C12—N4—C7—C8 | 21.4 (3) |
C2—C3—C4—C5 | 0.5 (4) | C12—C13—C14—C15 | −0.1 (3) |
C3—C4—C5—N1 | 0.0 (3) | C13—C12—C17—C16 | −1.4 (3) |
C3—C4—C5—C6 | 177.2 (2) | C13—C14—C15—Cl1 | 177.46 (13) |
C4—C5—C6—N2 | −29.4 (3) | C13—C14—C15—C16 | −1.2 (3) |
C4—C5—C6—N4 | 154.69 (18) | C14—C15—C16—C17 | 1.2 (3) |
C5—N1—C1—C2 | 0.5 (4) | C15—C16—C17—C12 | 0.1 (3) |
C6—N2—N3—C7 | −0.3 (2) | C17—C12—C13—C14 | 1.4 (3) |
C6—N4—C7—N3 | −0.51 (19) |
C17H11FN6 | Z = 2 |
Mr = 318.32 | F(000) = 328 |
Triclinic, P1 | Dx = 1.386 Mg m−3 |
a = 8.624 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.503 (2) Å | Cell parameters from 1265 reflections |
c = 10.471 (3) Å | θ = 2.4–22.0° |
α = 80.312 (3)° | µ = 0.10 mm−1 |
β = 81.512 (4)° | T = 293 K |
γ = 64.780 (3)° | Block, clear light colourless |
V = 762.5 (3) Å3 | 0.18 × 0.14 × 0.12 mm |
Bruker APEXII CCD area detector diffractometer | 1778 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
phi and ω scans | θmax = 25.1°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −10→10 |
Tmin = 0.984, Tmax = 0.988 | k = −11→11 |
5556 measured reflections | l = −12→12 |
2676 independent reflections |
Refinement on F2 | 13 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.138 | w = 1/[σ2(Fo2) + (0.0684P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
2676 reflections | Δρmax = 0.19 e Å−3 |
217 parameters | Δρmin = −0.23 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
F1 | 0.97294 (17) | 0.63947 (18) | 0.39616 (14) | 0.0802 (5) | |
N1 | 0.2472 (3) | 0.9553 (2) | 0.3243 (2) | 0.0768 (7) | |
N2 | 0.1623 (2) | 0.7479 (2) | 0.11258 (19) | 0.0584 (5) | |
N3 | 0.2434 (2) | 0.5876 (2) | 0.10485 (18) | 0.0557 (5) | |
N4 | 0.39664 (19) | 0.65217 (19) | 0.21641 (15) | 0.0406 (4) | |
N5 | 0.5977 (3) | 0.3235 (2) | 0.28799 (18) | 0.0611 (6) | |
N6 | 0.4896 (3) | 0.2738 (2) | 0.1124 (2) | 0.0671 (6) | |
C1 | 0.1997 (4) | 1.1000 (3) | 0.3536 (3) | 0.0963 (11) | |
H1 | 0.226224 | 1.111040 | 0.433238 | 0.116* | |
C2 | 0.1144 (4) | 1.2333 (3) | 0.2740 (3) | 0.0868 (9) | |
H2 | 0.086100 | 1.331697 | 0.298227 | 0.104* | |
C3 | 0.0725 (4) | 1.2181 (3) | 0.1592 (3) | 0.0786 (9) | |
H3 | 0.011934 | 1.306441 | 0.103914 | 0.094* | |
C4 | 0.1202 (3) | 1.0709 (3) | 0.1249 (2) | 0.0642 (7) | |
H4 | 0.094069 | 1.058242 | 0.045685 | 0.077* | |
C5 | 0.2070 (3) | 0.9428 (3) | 0.2098 (2) | 0.0511 (6) | |
C6 | 0.2547 (3) | 0.7834 (3) | 0.1791 (2) | 0.0473 (6) | |
C7 | 0.3832 (3) | 0.5337 (2) | 0.16723 (19) | 0.0425 (5) | |
C8 | 0.4998 (3) | 0.3667 (3) | 0.1904 (2) | 0.0452 (5) | |
C9 | 0.5904 (4) | 0.1226 (4) | 0.1394 (3) | 0.0834 (9) | |
H9 | 0.587265 | 0.052364 | 0.088908 | 0.100* | |
C10 | 0.6978 (4) | 0.0647 (3) | 0.2366 (3) | 0.0834 (9) | |
H10 | 0.767361 | −0.041583 | 0.252592 | 0.100* | |
C11 | 0.6978 (4) | 0.1712 (3) | 0.3093 (3) | 0.0785 (8) | |
H11 | 0.770398 | 0.136136 | 0.376134 | 0.094* | |
C12 | 0.5457 (2) | 0.6483 (2) | 0.26658 (19) | 0.0398 (5) | |
C13 | 0.5525 (3) | 0.6463 (2) | 0.3963 (2) | 0.0481 (6) | |
H13 | 0.459390 | 0.648340 | 0.454678 | 0.058* | |
C14 | 0.6985 (3) | 0.6414 (3) | 0.4407 (2) | 0.0543 (6) | |
H14 | 0.705748 | 0.638370 | 0.528956 | 0.065* | |
C15 | 0.8314 (3) | 0.6410 (3) | 0.3519 (2) | 0.0516 (6) | |
C16 | 0.8291 (3) | 0.6428 (3) | 0.2218 (2) | 0.0517 (6) | |
H16 | 0.923012 | 0.641668 | 0.164667 | 0.062* | |
C17 | 0.6847 (3) | 0.6465 (2) | 0.1761 (2) | 0.0468 (5) | |
H17 | 0.679518 | 0.647686 | 0.087790 | 0.056* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.0649 (10) | 0.1008 (12) | 0.0907 (11) | −0.0423 (9) | −0.0384 (8) | −0.0028 (9) |
N1 | 0.0919 (17) | 0.0484 (13) | 0.0765 (15) | −0.0051 (11) | −0.0370 (13) | −0.0119 (11) |
N2 | 0.0472 (11) | 0.0606 (13) | 0.0704 (13) | −0.0209 (10) | −0.0193 (10) | −0.0063 (10) |
N3 | 0.0498 (12) | 0.0662 (14) | 0.0604 (12) | −0.0296 (10) | −0.0129 (9) | −0.0090 (10) |
N4 | 0.0365 (10) | 0.0415 (10) | 0.0446 (10) | −0.0143 (8) | −0.0090 (8) | −0.0075 (8) |
N5 | 0.0760 (14) | 0.0442 (12) | 0.0597 (12) | −0.0170 (11) | −0.0186 (11) | −0.0074 (9) |
N6 | 0.0852 (16) | 0.0583 (14) | 0.0668 (14) | −0.0333 (13) | −0.0060 (11) | −0.0210 (11) |
C1 | 0.124 (3) | 0.0550 (18) | 0.090 (2) | −0.0032 (17) | −0.0455 (19) | −0.0194 (16) |
C2 | 0.099 (2) | 0.0508 (17) | 0.094 (2) | −0.0072 (15) | −0.0263 (18) | −0.0134 (16) |
C3 | 0.077 (2) | 0.0538 (17) | 0.0804 (19) | −0.0037 (15) | −0.0175 (16) | 0.0021 (14) |
C4 | 0.0564 (15) | 0.0623 (17) | 0.0613 (15) | −0.0110 (13) | −0.0156 (12) | −0.0024 (13) |
C5 | 0.0399 (12) | 0.0487 (14) | 0.0577 (14) | −0.0099 (10) | −0.0091 (10) | −0.0066 (11) |
C6 | 0.0372 (12) | 0.0534 (14) | 0.0502 (13) | −0.0164 (11) | −0.0103 (10) | −0.0038 (11) |
C7 | 0.0419 (12) | 0.0511 (13) | 0.0406 (12) | −0.0241 (10) | −0.0022 (9) | −0.0089 (10) |
C8 | 0.0481 (13) | 0.0528 (14) | 0.0431 (12) | −0.0288 (11) | 0.0037 (10) | −0.0126 (10) |
C9 | 0.112 (2) | 0.065 (2) | 0.084 (2) | −0.0427 (18) | 0.0028 (18) | −0.0306 (16) |
C10 | 0.107 (2) | 0.0426 (15) | 0.089 (2) | −0.0205 (15) | −0.0019 (18) | −0.0112 (15) |
C11 | 0.094 (2) | 0.0514 (17) | 0.0813 (19) | −0.0182 (15) | −0.0244 (16) | −0.0023 (14) |
C12 | 0.0365 (11) | 0.0365 (11) | 0.0478 (12) | −0.0131 (9) | −0.0136 (9) | −0.0053 (9) |
C13 | 0.0475 (13) | 0.0528 (14) | 0.0445 (13) | −0.0203 (11) | −0.0068 (10) | −0.0054 (10) |
C14 | 0.0628 (16) | 0.0577 (15) | 0.0466 (13) | −0.0251 (12) | −0.0206 (12) | −0.0024 (11) |
C15 | 0.0455 (13) | 0.0473 (13) | 0.0678 (16) | −0.0195 (11) | −0.0264 (12) | −0.0025 (11) |
C16 | 0.0398 (12) | 0.0593 (15) | 0.0590 (14) | −0.0222 (11) | −0.0065 (10) | −0.0081 (11) |
C17 | 0.0440 (12) | 0.0508 (13) | 0.0479 (13) | −0.0193 (11) | −0.0097 (10) | −0.0076 (10) |
F1—C15 | 1.362 (2) | C4—H4 | 0.9300 |
N1—C1 | 1.334 (3) | C4—C5 | 1.374 (3) |
N1—C5 | 1.333 (3) | C5—C6 | 1.470 (3) |
N2—N3 | 1.390 (3) | C7—C8 | 1.474 (3) |
N2—C6 | 1.306 (3) | C9—H9 | 0.9300 |
N3—C7 | 1.317 (2) | C9—C10 | 1.360 (4) |
N4—C6 | 1.372 (2) | C10—H10 | 0.9300 |
N4—C7 | 1.368 (2) | C10—C11 | 1.365 (4) |
N4—C12 | 1.443 (2) | C11—H11 | 0.9300 |
N5—C8 | 1.320 (3) | C12—C13 | 1.365 (3) |
N5—C11 | 1.332 (3) | C12—C17 | 1.410 (3) |
N6—C8 | 1.335 (3) | C13—H13 | 0.9300 |
N6—C9 | 1.331 (4) | C13—C14 | 1.385 (3) |
C1—H1 | 0.9300 | C14—H14 | 0.9300 |
C1—C2 | 1.368 (4) | C14—C15 | 1.365 (3) |
C2—H2 | 0.9300 | C15—C16 | 1.362 (3) |
C2—C3 | 1.352 (4) | C16—H16 | 0.9300 |
C3—H3 | 0.9300 | C16—C17 | 1.384 (3) |
C3—C4 | 1.375 (4) | C17—H17 | 0.9300 |
C5—N1—C1 | 116.7 (2) | N5—C8—C7 | 117.32 (18) |
C6—N2—N3 | 107.64 (17) | N6—C8—C7 | 115.7 (2) |
C7—N3—N2 | 106.77 (17) | N6—C9—H9 | 118.1 |
C6—N4—C12 | 126.52 (17) | N6—C9—C10 | 123.9 (3) |
C7—N4—C6 | 104.51 (16) | C10—C9—H9 | 118.1 |
C7—N4—C12 | 127.31 (17) | C9—C10—H10 | 121.8 |
C8—N5—C11 | 116.1 (2) | C9—C10—C11 | 116.4 (3) |
C9—N6—C8 | 114.4 (2) | C11—C10—H10 | 121.8 |
N1—C1—H1 | 117.9 | N5—C11—C10 | 122.3 (3) |
N1—C1—C2 | 124.2 (3) | N5—C11—H11 | 118.8 |
C2—C1—H1 | 117.9 | C10—C11—H11 | 118.8 |
C1—C2—H2 | 120.9 | C13—C12—N4 | 121.55 (18) |
C3—C2—C1 | 118.2 (3) | C13—C12—C17 | 121.15 (18) |
C3—C2—H2 | 120.9 | C17—C12—N4 | 117.29 (17) |
C2—C3—H3 | 120.3 | C12—C13—H13 | 120.1 |
C2—C3—C4 | 119.4 (3) | C12—C13—C14 | 119.8 (2) |
C4—C3—H3 | 120.3 | C14—C13—H13 | 120.1 |
C3—C4—H4 | 120.6 | C13—C14—H14 | 120.8 |
C5—C4—C3 | 118.8 (2) | C15—C14—C13 | 118.4 (2) |
C5—C4—H4 | 120.6 | C15—C14—H14 | 120.8 |
N1—C5—C4 | 122.7 (2) | F1—C15—C14 | 118.0 (2) |
N1—C5—C6 | 116.71 (19) | F1—C15—C16 | 118.6 (2) |
C4—C5—C6 | 120.6 (2) | C16—C15—C14 | 123.40 (19) |
N2—C6—N4 | 110.47 (19) | C15—C16—H16 | 120.6 |
N2—C6—C5 | 123.29 (19) | C15—C16—C17 | 118.9 (2) |
N4—C6—C5 | 126.23 (18) | C17—C16—H16 | 120.6 |
N3—C7—N4 | 110.62 (19) | C12—C17—H17 | 120.8 |
N3—C7—C8 | 124.28 (19) | C16—C17—C12 | 118.39 (19) |
N4—C7—C8 | 124.89 (18) | C16—C17—H17 | 120.8 |
N5—C8—N6 | 126.9 (2) | ||
F1—C15—C16—C17 | −179.15 (19) | C6—N4—C7—C8 | −175.15 (19) |
N1—C1—C2—C3 | 1.3 (5) | C6—N4—C12—C13 | 88.4 (3) |
N1—C5—C6—N2 | 145.4 (2) | C6—N4—C12—C17 | −91.7 (3) |
N1—C5—C6—N4 | −33.3 (3) | C7—N4—C6—N2 | 0.0 (2) |
N2—N3—C7—N4 | 0.4 (2) | C7—N4—C6—C5 | 178.8 (2) |
N2—N3—C7—C8 | 175.31 (18) | C7—N4—C12—C13 | −108.6 (2) |
N3—N2—C6—N4 | 0.2 (2) | C7—N4—C12—C17 | 71.3 (3) |
N3—N2—C6—C5 | −178.7 (2) | C8—N5—C11—C10 | −1.2 (4) |
N3—C7—C8—N5 | −157.6 (2) | C8—N6—C9—C10 | −0.9 (4) |
N3—C7—C8—N6 | 19.9 (3) | C9—N6—C8—N5 | 0.2 (4) |
N4—C7—C8—N5 | 16.7 (3) | C9—N6—C8—C7 | −177.0 (2) |
N4—C7—C8—N6 | −165.86 (19) | C9—C10—C11—N5 | 0.6 (4) |
N4—C12—C13—C14 | 179.48 (19) | C11—N5—C8—N6 | 0.8 (4) |
N4—C12—C17—C16 | 179.98 (18) | C11—N5—C8—C7 | 178.0 (2) |
N6—C9—C10—C11 | 0.5 (5) | C12—N4—C6—N2 | 166.09 (19) |
C1—N1—C5—C4 | −0.4 (4) | C12—N4—C6—C5 | −15.1 (3) |
C1—N1—C5—C6 | −178.2 (2) | C12—N4—C7—N3 | −166.18 (18) |
C1—C2—C3—C4 | −1.7 (5) | C12—N4—C7—C8 | 18.9 (3) |
C2—C3—C4—C5 | 1.1 (4) | C12—C13—C14—C15 | 1.0 (3) |
C3—C4—C5—N1 | 0.0 (4) | C13—C12—C17—C16 | −0.1 (3) |
C3—C4—C5—C6 | 177.7 (2) | C13—C14—C15—F1 | 178.62 (19) |
C4—C5—C6—N2 | −32.5 (3) | C13—C14—C15—C16 | −1.0 (4) |
C4—C5—C6—N4 | 148.8 (2) | C14—C15—C16—C17 | 0.5 (4) |
C5—N1—C1—C2 | −0.2 (5) | C15—C16—C17—C12 | 0.1 (3) |
C6—N2—N3—C7 | −0.4 (2) | C17—C12—C13—C14 | −0.4 (3) |
C6—N4—C7—N3 | −0.2 (2) |
C18H14N6 | Dx = 1.279 Mg m−3 |
Mr = 314.35 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 3494 reflections |
a = 15.7069 (10) Å | θ = 2.5–29.1° |
b = 11.8266 (11) Å | µ = 0.08 mm−1 |
c = 17.5763 (12) Å | T = 293 K |
V = 3265.0 (4) Å3 | Block, colourless |
Z = 8 | 0.17 × 0.16 × 0.15 mm |
F(000) = 1312 |
Rigaku XtaLAB Synergy-R DW diffractometer with a HyPix detector | 1901 reflections with I > 2σ(I) |
ω scans | Rint = 0.116 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | θmax = 25.1°, θmin = 2.3° |
Tmin = 0.986, Tmax = 0.988 | h = −18→17 |
13041 measured reflections | k = −14→12 |
2885 independent reflections | l = −19→20 |
Refinement on F2 | 84 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.054 | H-atom parameters constrained |
wR(F2) = 0.157 | w = 1/[σ2(Fo2) + (0.0911P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max < 0.001 |
2885 reflections | Δρmax = 0.17 e Å−3 |
264 parameters | Δρmin = −0.24 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1 | 0.7327 (6) | 0.7143 (9) | 0.7364 (6) | 0.072 (2) | 0.463 (15) |
N1A | 0.7685 (8) | 0.5238 (10) | 0.6743 (9) | 0.077 (3) | 0.537 (15) |
N2 | 0.57795 (11) | 0.6717 (2) | 0.66033 (10) | 0.0738 (6) | |
N3 | 0.52512 (11) | 0.67512 (19) | 0.59781 (10) | 0.0689 (6) | |
N4 | 0.65335 (8) | 0.63004 (14) | 0.55907 (9) | 0.0446 (4) | |
N5 | 0.59188 (11) | 0.69239 (18) | 0.40577 (10) | 0.0651 (5) | |
N6 | 0.45851 (10) | 0.62154 (16) | 0.44943 (11) | 0.0613 (5) | |
C1 | 0.7947 (7) | 0.7092 (12) | 0.7837 (6) | 0.092 (3) | 0.463 (15) |
H1 | 0.799769 | 0.765967 | 0.819973 | 0.110* | 0.463 (15) |
C1A | 0.8367 (6) | 0.4992 (8) | 0.7145 (6) | 0.078 (2) | 0.537 (15) |
H1A | 0.865411 | 0.431957 | 0.704875 | 0.094* | 0.537 (15) |
C2 | 0.8541 (6) | 0.6240 (15) | 0.7834 (5) | 0.086 (3) | 0.463 (15) |
H2 | 0.897391 | 0.622952 | 0.819459 | 0.103* | 0.463 (15) |
C2A | 0.8672 (5) | 0.5713 (8) | 0.7713 (5) | 0.069 (2) | 0.537 (15) |
H2A | 0.914895 | 0.552054 | 0.799861 | 0.083* | 0.537 (15) |
C3 | 0.8491 (6) | 0.5408 (14) | 0.7296 (7) | 0.090 (3) | 0.463 (15) |
H3 | 0.889682 | 0.483550 | 0.727983 | 0.108* | 0.463 (15) |
C3A | 0.8251 (6) | 0.6708 (7) | 0.7839 (4) | 0.0682 (19) | 0.537 (15) |
H3A | 0.842542 | 0.720597 | 0.821815 | 0.082* | 0.537 (15) |
C4 | 0.7824 (10) | 0.5426 (15) | 0.6771 (11) | 0.076 (3) | 0.463 (15) |
H4 | 0.776377 | 0.488276 | 0.639198 | 0.091* | 0.463 (15) |
C4A | 0.7561 (7) | 0.6946 (10) | 0.7387 (7) | 0.0680 (18) | 0.537 (15) |
H4A | 0.727409 | 0.762402 | 0.746512 | 0.082* | 0.537 (15) |
C5 | 0.72861 (13) | 0.6272 (2) | 0.68533 (12) | 0.0612 (6) | |
C6 | 0.65382 (12) | 0.64461 (19) | 0.63607 (11) | 0.0556 (6) | |
C7 | 0.57106 (11) | 0.65062 (17) | 0.53805 (11) | 0.0486 (5) | |
C8 | 0.53903 (11) | 0.65312 (17) | 0.45930 (11) | 0.0461 (5) | |
C9 | 0.43020 (15) | 0.6304 (2) | 0.37810 (16) | 0.0722 (7) | |
H9 | 0.374351 | 0.608988 | 0.368030 | 0.087* | |
C10 | 0.47852 (18) | 0.6690 (2) | 0.31916 (14) | 0.0767 (8) | |
H10 | 0.456760 | 0.673876 | 0.270055 | 0.092* | |
C11 | 0.56022 (17) | 0.7002 (2) | 0.33530 (13) | 0.0740 (7) | |
H11 | 0.594684 | 0.727501 | 0.296399 | 0.089* | |
C12 | 0.72520 (10) | 0.59963 (16) | 0.51216 (11) | 0.0429 (5) | |
C13 | 0.72638 (11) | 0.49870 (19) | 0.47468 (13) | 0.0547 (5) | |
H13 | 0.679812 | 0.450259 | 0.477123 | 0.066* | |
C14 | 0.79750 (13) | 0.4693 (2) | 0.43310 (14) | 0.0672 (7) | |
H14 | 0.798442 | 0.400489 | 0.407559 | 0.081* | |
C15 | 0.86783 (12) | 0.5404 (2) | 0.42854 (13) | 0.0604 (6) | |
C16 | 0.86363 (12) | 0.6421 (2) | 0.46576 (14) | 0.0623 (6) | |
H16 | 0.909371 | 0.691848 | 0.462664 | 0.075* | |
C17 | 0.79330 (12) | 0.67211 (19) | 0.50752 (12) | 0.0539 (5) | |
H17 | 0.791778 | 0.741324 | 0.532589 | 0.065* | |
C18 | 0.94599 (16) | 0.5079 (3) | 0.38356 (19) | 0.0980 (10) | |
H18A | 0.981640 | 0.573071 | 0.376907 | 0.147* | |
H18B | 0.929106 | 0.479457 | 0.334676 | 0.147* | |
H18C | 0.976901 | 0.450441 | 0.410504 | 0.147* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.061 (4) | 0.107 (5) | 0.047 (3) | 0.001 (3) | −0.008 (3) | −0.016 (3) |
N1A | 0.063 (5) | 0.093 (3) | 0.074 (4) | 0.008 (3) | −0.021 (4) | −0.004 (3) |
N2 | 0.0595 (11) | 0.1190 (18) | 0.0427 (10) | 0.0293 (10) | 0.0036 (9) | −0.0048 (10) |
N3 | 0.0510 (10) | 0.1107 (17) | 0.0448 (10) | 0.0258 (9) | 0.0043 (8) | −0.0004 (9) |
N4 | 0.0369 (8) | 0.0571 (11) | 0.0398 (9) | 0.0040 (6) | 0.0037 (7) | −0.0016 (7) |
N5 | 0.0602 (10) | 0.0851 (15) | 0.0499 (11) | −0.0041 (9) | 0.0047 (9) | 0.0098 (9) |
N6 | 0.0437 (9) | 0.0784 (14) | 0.0620 (12) | 0.0004 (8) | −0.0043 (9) | 0.0012 (9) |
C1 | 0.068 (5) | 0.140 (7) | 0.067 (4) | −0.003 (4) | −0.015 (4) | 0.005 (5) |
C1A | 0.069 (3) | 0.088 (4) | 0.077 (4) | 0.000 (3) | −0.027 (3) | −0.002 (3) |
C2 | 0.058 (4) | 0.141 (9) | 0.058 (4) | 0.004 (5) | −0.013 (4) | 0.018 (6) |
C2A | 0.054 (3) | 0.091 (4) | 0.063 (4) | −0.002 (3) | −0.013 (3) | 0.001 (3) |
C3 | 0.058 (4) | 0.142 (8) | 0.070 (5) | 0.004 (5) | −0.017 (4) | 0.019 (6) |
C3A | 0.063 (4) | 0.091 (4) | 0.051 (3) | 0.000 (3) | −0.011 (3) | 0.003 (3) |
C4 | 0.045 (4) | 0.117 (6) | 0.065 (6) | 0.019 (5) | −0.008 (4) | 0.021 (5) |
C4A | 0.062 (4) | 0.096 (4) | 0.045 (3) | 0.009 (3) | −0.008 (3) | −0.004 (2) |
C5 | 0.0477 (11) | 0.0935 (16) | 0.0425 (11) | −0.0015 (10) | 0.0007 (9) | 0.0019 (10) |
C6 | 0.0502 (11) | 0.0748 (15) | 0.0416 (11) | 0.0082 (9) | 0.0007 (9) | −0.0048 (9) |
C7 | 0.0368 (9) | 0.0627 (13) | 0.0461 (11) | 0.0095 (8) | 0.0046 (8) | 0.0014 (9) |
C8 | 0.0392 (9) | 0.0541 (12) | 0.0450 (11) | 0.0058 (7) | 0.0020 (8) | 0.0023 (8) |
C9 | 0.0571 (13) | 0.0838 (18) | 0.0756 (17) | 0.0076 (11) | −0.0186 (13) | −0.0107 (13) |
C10 | 0.0930 (19) | 0.090 (2) | 0.0466 (13) | 0.0229 (14) | −0.0167 (13) | −0.0050 (12) |
C11 | 0.0839 (17) | 0.091 (2) | 0.0475 (13) | 0.0027 (13) | 0.0076 (13) | 0.0108 (12) |
C12 | 0.0341 (8) | 0.0530 (12) | 0.0416 (10) | 0.0002 (7) | 0.0034 (8) | 0.0010 (8) |
C13 | 0.0405 (10) | 0.0586 (13) | 0.0648 (13) | −0.0064 (8) | 0.0083 (10) | −0.0091 (10) |
C14 | 0.0545 (11) | 0.0686 (16) | 0.0786 (17) | −0.0034 (10) | 0.0156 (12) | −0.0217 (12) |
C15 | 0.0438 (10) | 0.0756 (17) | 0.0618 (14) | 0.0020 (9) | 0.0145 (10) | −0.0028 (11) |
C16 | 0.0418 (10) | 0.0722 (16) | 0.0730 (16) | −0.0125 (9) | 0.0089 (10) | 0.0013 (12) |
C17 | 0.0465 (10) | 0.0546 (13) | 0.0605 (14) | −0.0068 (8) | 0.0048 (10) | −0.0068 (10) |
C18 | 0.0659 (15) | 0.120 (3) | 0.108 (2) | 0.0026 (15) | 0.0404 (16) | −0.0081 (18) |
N1—C1 | 1.283 (10) | C4—H4 | 0.9300 |
N1—C5 | 1.368 (10) | C4—C5 | 1.317 (14) |
N1A—C1A | 1.316 (11) | C4A—H4A | 0.9300 |
N1A—C5 | 1.387 (11) | C4A—C5 | 1.304 (11) |
N2—N3 | 1.377 (2) | C5—C6 | 1.474 (3) |
N2—C6 | 1.306 (2) | C7—C8 | 1.473 (3) |
N3—C7 | 1.307 (2) | C9—H9 | 0.9300 |
N4—C6 | 1.364 (2) | C9—C10 | 1.363 (4) |
N4—C7 | 1.366 (2) | C10—H10 | 0.9300 |
N4—C12 | 1.443 (2) | C10—C11 | 1.365 (4) |
N5—C8 | 1.338 (2) | C11—H11 | 0.9300 |
N5—C11 | 1.338 (3) | C12—C13 | 1.364 (3) |
N6—C8 | 1.330 (2) | C12—C17 | 1.373 (3) |
N6—C9 | 1.334 (3) | C13—H13 | 0.9300 |
C1—H1 | 0.9300 | C13—C14 | 1.379 (3) |
C1—C2 | 1.373 (11) | C14—H14 | 0.9300 |
C1A—H1A | 0.9300 | C14—C15 | 1.390 (3) |
C1A—C2A | 1.397 (9) | C15—C16 | 1.371 (3) |
C2—H2 | 0.9300 | C15—C18 | 1.510 (3) |
C2—C3 | 1.367 (11) | C16—H16 | 0.9300 |
C2A—H2A | 0.9300 | C16—C17 | 1.373 (3) |
C2A—C3A | 1.369 (9) | C17—H17 | 0.9300 |
C3—H3 | 0.9300 | C18—H18A | 0.9600 |
C3—C4 | 1.397 (13) | C18—H18B | 0.9600 |
C3A—H3A | 0.9300 | C18—H18C | 0.9600 |
C3A—C4A | 1.373 (10) | ||
C1—N1—C5 | 115.1 (7) | N4—C6—C5 | 124.72 (17) |
C1A—N1A—C5 | 119.2 (9) | N3—C7—N4 | 110.15 (17) |
C6—N2—N3 | 107.25 (17) | N3—C7—C8 | 124.22 (16) |
C7—N3—N2 | 107.59 (16) | N4—C7—C8 | 125.51 (16) |
C6—N4—C7 | 104.54 (15) | N5—C8—C7 | 117.12 (16) |
C6—N4—C12 | 126.43 (14) | N6—C8—N5 | 126.56 (18) |
C7—N4—C12 | 129.03 (16) | N6—C8—C7 | 116.21 (17) |
C11—N5—C8 | 116.38 (19) | N6—C9—H9 | 118.1 |
C8—N6—C9 | 114.7 (2) | N6—C9—C10 | 123.7 (2) |
N1—C1—H1 | 118.3 | C10—C9—H9 | 118.1 |
N1—C1—C2 | 123.3 (9) | C9—C10—H10 | 121.4 |
C2—C1—H1 | 118.3 | C9—C10—C11 | 117.1 (2) |
N1A—C1A—H1A | 119.1 | C11—C10—H10 | 121.4 |
N1A—C1A—C2A | 121.9 (9) | N5—C11—C10 | 121.6 (2) |
C2A—C1A—H1A | 119.1 | N5—C11—H11 | 119.2 |
C1—C2—H2 | 120.3 | C10—C11—H11 | 119.2 |
C3—C2—C1 | 119.5 (8) | C13—C12—N4 | 120.32 (15) |
C3—C2—H2 | 120.3 | C13—C12—C17 | 120.47 (17) |
C1A—C2A—H2A | 120.8 | C17—C12—N4 | 119.18 (17) |
C3A—C2A—C1A | 118.4 (8) | C12—C13—H13 | 120.4 |
C3A—C2A—H2A | 120.8 | C12—C13—C14 | 119.16 (18) |
C2—C3—H3 | 120.4 | C14—C13—H13 | 120.4 |
C2—C3—C4 | 119.3 (10) | C13—C14—H14 | 119.3 |
C4—C3—H3 | 120.4 | C13—C14—C15 | 121.5 (2) |
C2A—C3A—H3A | 121.2 | C15—C14—H14 | 119.3 |
C2A—C3A—C4A | 117.6 (8) | C14—C15—C18 | 121.5 (2) |
C4A—C3A—H3A | 121.2 | C16—C15—C14 | 117.70 (19) |
C3—C4—H4 | 122.6 | C16—C15—C18 | 120.8 (2) |
C5—C4—C3 | 114.8 (12) | C15—C16—H16 | 119.3 |
C5—C4—H4 | 122.6 | C15—C16—C17 | 121.36 (19) |
C3A—C4A—H4A | 118.2 | C17—C16—H16 | 119.3 |
C5—C4A—C3A | 123.5 (8) | C12—C17—H17 | 120.1 |
C5—C4A—H4A | 118.2 | C16—C17—C12 | 119.8 (2) |
N1—C5—C6 | 108.5 (4) | C16—C17—H17 | 120.1 |
N1A—C5—C6 | 113.6 (5) | C15—C18—H18A | 109.5 |
C4—C5—N1 | 127.9 (7) | C15—C18—H18B | 109.5 |
C4—C5—C6 | 123.5 (7) | C15—C18—H18C | 109.5 |
C4A—C5—N1A | 119.3 (6) | H18A—C18—H18B | 109.5 |
C4A—C5—C6 | 126.9 (4) | H18A—C18—H18C | 109.5 |
N2—C6—N4 | 110.48 (17) | H18B—C18—H18C | 109.5 |
N2—C6—C5 | 124.75 (19) | ||
N1—C1—C2—C3 | 1.3 (15) | C4A—C5—C6—N4 | 133.2 (7) |
N1—C5—C6—N2 | −46.4 (7) | C5—N1—C1—C2 | 0.9 (14) |
N1—C5—C6—N4 | 136.5 (6) | C5—N1A—C1A—C2A | 4.0 (18) |
N1A—C1A—C2A—C3A | −1.1 (14) | C6—N2—N3—C7 | −0.4 (3) |
N1A—C5—C6—N2 | 126.3 (8) | C6—N4—C7—N3 | −0.3 (2) |
N1A—C5—C6—N4 | −50.9 (8) | C6—N4—C7—C8 | 175.63 (19) |
N2—N3—C7—N4 | 0.4 (3) | C6—N4—C12—C13 | 114.7 (2) |
N2—N3—C7—C8 | −175.6 (2) | C6—N4—C12—C17 | −63.5 (3) |
N3—N2—C6—N4 | 0.2 (3) | C7—N4—C6—N2 | 0.1 (2) |
N3—N2—C6—C5 | −177.3 (2) | C7—N4—C6—C5 | 177.6 (2) |
N3—C7—C8—N5 | 141.3 (2) | C7—N4—C12—C13 | −65.3 (3) |
N3—C7—C8—N6 | −35.2 (3) | C7—N4—C12—C17 | 116.5 (2) |
N4—C7—C8—N5 | −34.1 (3) | C8—N5—C11—C10 | −0.4 (4) |
N4—C7—C8—N6 | 149.4 (2) | C8—N6—C9—C10 | −0.3 (3) |
N4—C12—C13—C14 | −176.98 (19) | C9—N6—C8—N5 | 0.5 (3) |
N4—C12—C17—C16 | 177.20 (19) | C9—N6—C8—C7 | 176.68 (18) |
N6—C9—C10—C11 | −0.2 (4) | C9—C10—C11—N5 | 0.5 (4) |
C1—N1—C5—C4 | −3.3 (19) | C11—N5—C8—N6 | −0.2 (3) |
C1—N1—C5—C6 | 179.3 (8) | C11—N5—C8—C7 | −176.3 (2) |
C1—C2—C3—C4 | −1.5 (17) | C12—N4—C6—N2 | −179.9 (2) |
C1A—N1A—C5—C4A | −4.5 (18) | C12—N4—C6—C5 | −2.4 (3) |
C1A—N1A—C5—C6 | 179.2 (10) | C12—N4—C7—N3 | 179.67 (19) |
C1A—C2A—C3A—C4A | −1.2 (13) | C12—N4—C7—C8 | −4.4 (3) |
C2—C3—C4—C5 | 0 (2) | C12—C13—C14—C15 | −0.1 (4) |
C2A—C3A—C4A—C5 | 0.6 (16) | C13—C12—C17—C16 | −1.0 (3) |
C3—C4—C5—N1 | 3 (2) | C13—C14—C15—C16 | −1.2 (4) |
C3—C4—C5—C6 | −179.9 (9) | C13—C14—C15—C18 | 179.5 (2) |
C3A—C4A—C5—N1A | 2.2 (16) | C14—C15—C16—C17 | 1.4 (4) |
C3A—C4A—C5—C6 | 177.9 (7) | C15—C16—C17—C12 | −0.3 (4) |
C4—C5—C6—N2 | 136.0 (12) | C17—C12—C13—C14 | 1.2 (3) |
C4—C5—C6—N4 | −41.1 (12) | C18—C15—C16—C17 | −179.3 (2) |
C4A—C5—C6—N2 | −49.6 (8) |
L2·C2H5OH | L2 | L3 | L4 | L5 | L6 | |
N1—C1 | 1.329 (4) | 1.283 (10) | 1.336 (3) | 1.336 (5) | 1.334 (3) | 1.334 (3) |
N2—N3 | 1.380 (3) | 1.377 (2) | 1.387 (3) | 1.380 (4) | 1.377 (2) | 1.390 (3) |
N4—C6 | 1.368 (3) | 1.364 (2) | 1.367 (2) | 1.374 (3) | 1.368 (2) | 1.372 (2) |
N5—C8 | 1.334 (4) | 1.338 (2) | 1.329 (3) | 1.329 (4) | 1.329 (3) | 1.321 (3) |
N6—C8 | 1.330 (3) | 1.330 (2) | 1.332 (3) | 1.333 (4) | 1.337 (2) | 1.335 (3) |
C18—C15 | 1.515 (4) | 1.510 (3) | ||||
O1—C20 | 1.391 (6) | |||||
Br1—C15 | 1.902 (3) | |||||
Cl1—C15 | 1.749 (6) | |||||
F1—C15 | 1.361 (2) | |||||
C1—N1—C5 | 116.4 (3) | 115.1 (7) | 115.8 (2) | 117.1 (3) | 116.5 (2) | 116.7 (2) |
C6—N2—N3 | 107.1 (2) | 107.25 (17) | 107.5 (2) | 107.7 (2) | 107.5 (2) | 107.6 (2) |
C7—N3—N2 | 107.6 (2) | 107.58 (16) | 107.2 (2) | 107.6 (2) | 107.3 (2) | 106.8 (2) |
C7—N4—C6 | 104.3 (2) | 104.54 (15) | 104.6 (2) | 104.5 (2) | 104.2 (3) | 104.5 (2) |
C8—N5—C11 | 115.0 (3) | 116.38 (19) | 115.1 (2) | 115.9 (3) | 116.0 (2) | 116.1 (2) |
C8—N6—C9 | 114.7 (3) | 114.7 (2) | 115.3 (2) | 115.4 (3) | 114.5 (2) | 114.4 (2) |
C18—C15—C14 | 121.4 (3) | 111.3 (7) | ||||
O1—C20—C19 | 120.2 (4) | |||||
Br1—C15—C14 | 119.1 (2) | |||||
Cl1—C15—C14 | 119.0 (2) | |||||
F1—C15—C14 | 118.0 (2) |
Compound | Py/Trz | Ph/Trz | Pym/Trz |
L2·C2H5OH | 34.4 (2) | 87.2 (4) | 34.7 (3) |
L2 | 50.1 (3) | 64.4 (5) | 35.4 (4) |
L3 | 36.4 (1) | 51.3 (3) | 55.6 (1) |
L4 | 32.7 (7) | 78.0 (1) | 15.0 (5) |
L5 | 29.2 (2) | 80.4 (6) | 21.8 (6) |
L6 | 33.1 (3) | 80.4 (2) | 19.0 (1) |
Compound | D—H···A | D—H | H···A | D···A | D—H···A |
L2·C2H5OH | O1—H1A···N3 | 0.82 | 2.077 | 2.894 (1) | 174 |
C11—H11···O1i | 0.93 | 2.665 | 3.328 (3) | 129 | |
C17—H17···N6ii | 0.93 | 2.705 | 3.570 (2) | 155 | |
C2—H2···π(Ph)iii | 0.93 | 3.072 | 3.821 (3) | 139 | |
L2 | C2A—H2A···N3i | 0.93 | 2.553 | 3.455 (2) | 164 |
C11—H11···N1Aii | 0.93 | 2.505 | 3.372 (4) | 155 | |
C13—H13···N6iii | 0.93 | 2.666 | 3.498 (3) | 149 | |
L3 | C9—H9···N3i | 0.93 | 2.736 | 3.467 (2) | 136 |
C11—H11···N5ii | 0.93 | 2.665 | 3.401 (1) | 138 | |
C15—H15···N2iii | 0.93 | 2.541 | 3.415 (3) | 157 | |
L4 | C13—H13···N6i | 0.93 | 2.574 | 3.403 (1) | 149 |
C14—H14···N2ii | 0.93 | 2.643 | 3.469 (3) | 148 | |
C10—H10···π(Ph)iii | 0.93 | 3.185 | 3.911 (1) | 136 | |
L5 | C16—H16···N2i | 0.93 | 2.570 | 3.405 (1) | 150 |
C17—H17···N6ii | 0.93 | 2.640 | 3.470 (6) | 149 | |
C10–H10···π(Ph)iii | 0.93 | 3.146 | 3.854 (1) | 134 | |
L6 | C13—H13···N5i | 0.93 | 2.704 | 3.380 (1) | 130 |
C16—H16···N2ii | 0.93 | 2.613 | 3.412 (4) | 144 | |
C17—H17···N6iii | 0.93 | 2.554 | 3.399 (2) | 151 | |
C10—H10···π(Ph)iv | 0.93 | 3.267 | 3.965 (1) | 133 |
Symmetry codes for L2·C2H5OH: (i) -x+1, -y, -z+1; (ii) -x+1, -y+1, -z+1; (iii) x+1, y, z. For L2: (i) x+1/2, y, -z+3/2; (ii) x, -y+3/2, z-0.5; (iii) -x+1, -y+1, -z+1. For L3: (i) x-1/2, -y+3/2, -z+1; (ii) -x+1, -y+1, -z+1; (iii) -x+1/2, y-1/2, z. For L4: (i) -x+1, -y+1, -z+2; (ii) x+1, y, z; (iii) x-1, y+1, z. For L5: (i) x+1, y, z; (ii) -x+1, -y+1, -z; (iii) x, y-1, z. For L6: (i) -x+1, -y+1, -z+1; (ii) x+1, y, z; (iii) -x+1, -y+1, -z; (iv) x, y-1, z. |
Compound | X···π interaction | X···cent |
L4 | Br···π(Trz)ii | 3.562 (4) |
L5 | Cl···π(Trz)i | 3.422 (6) |
L6 | F···π(Trz)ii | 3.469 (3) |
Symmetry code: (i/ii) x+1, y, z. |
Contact | L2·C2H5OH | L2 | L3 | L4 | L5 | L6 |
H···H | 54.5 | 47.0 | 36.7 | 30.4 | 32.4 | 32.8 |
N···H/H···N | 16.1 | 28.2 | 31.6 | 21.8 | 22.2 | 23.8 |
C···H/H···C | 18.1 | 20.6 | 25.6 | 21.9 | 20.6 | 21.9 |
O···H/H···O | 5.1 | |||||
N···C/C···N | 1.9 | 1.9 | 3.4 | 4.6 | 4.3 | 4.4 |
C···C | 3 | 1.5 | 1.9 | 2.7 | 2.8 | 2.8 |
N···N | 1.3 | 0.8 | 0.8 | 1 | 1.3 | 1.1 |
Br···H/H···Br | 10.9 | |||||
Br···N/N···Br | 3.1 | |||||
Br···C/C···Br | 2.5 | |||||
Br···Br | 1.2 | |||||
Cl···H/H···Cl | 10.8 | |||||
Cl···N/N···Cl | 2.4 | |||||
Cl···C/C···Cl | 2.7 | |||||
Cl···Cl | 0.4 | |||||
F···H/H···F | 9.3 | |||||
F···N/N···F | 1.6 | |||||
F···C/C···F | 1.6 | |||||
F···F | 0.6 |