Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229613031598/gz3240sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229613031598/gz3240Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229613031598/gz3240IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229613031598/gz3240IIIsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229613031598/gz3240IVsup5.hkl |
CCDC references: 972772; 972773; 972774; 972775
For all compounds, data collection: SMART (Bruker, 2003); cell refinement: SMART (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
C26H20N6 | Z = 2 |
Mr = 416.48 | F(000) = 436 |
Triclinic, P1 | Dx = 1.348 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.094 (4) Å | Cell parameters from 1073 reflections |
b = 10.183 (4) Å | θ = 2.4–22.6° |
c = 10.972 (4) Å | µ = 0.08 mm−1 |
α = 106.389 (5)° | T = 298 K |
β = 103.167 (5)° | Block, yellow |
γ = 98.409 (5)° | 0.21 × 0.14 × 0.10 mm |
V = 1026.4 (6) Å3 |
Bruker SMART CCD area-detector diffractometer | 3762 independent reflections |
Radiation source: fine-focus sealed tube | 2341 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
phi and ω scans | θmax = 25.5°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | h = −12→12 |
Tmin = 0.986, Tmax = 0.992 | k = −12→8 |
5451 measured reflections | l = −10→13 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.077 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.200 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0943P)2] where P = (Fo2 + 2Fc2)/3 |
3762 reflections | (Δ/σ)max < 0.001 |
289 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.4589 (4) | −0.0172 (4) | 0.1635 (4) | 0.0661 (10) | |
H1 | 0.4161 | −0.1078 | 0.1552 | 0.079* | |
C2 | 0.3778 (4) | 0.0619 (3) | 0.1108 (3) | 0.0568 (9) | |
H2 | 0.2827 | 0.0254 | 0.0703 | 0.068* | |
C3 | 0.4378 (3) | 0.1945 (3) | 0.1182 (3) | 0.0427 (7) | |
C4 | 0.5782 (3) | 0.2430 (3) | 0.1807 (3) | 0.0535 (9) | |
H4 | 0.6240 | 0.3325 | 0.1887 | 0.064* | |
C5 | 0.6503 (4) | 0.1551 (4) | 0.2316 (3) | 0.0600 (9) | |
H5 | 0.7455 | 0.1890 | 0.2733 | 0.072* | |
C6 | 0.3519 (3) | 0.2804 (3) | 0.0548 (3) | 0.0503 (8) | |
H6A | 0.3428 | 0.2499 | −0.0394 | 0.060* | |
H6B | 0.2590 | 0.2622 | 0.0656 | 0.060* | |
C7 | 0.4875 (3) | 0.5212 (3) | 0.0652 (3) | 0.0414 (7) | |
C8 | 0.4107 (3) | 0.5116 (3) | 0.2359 (3) | 0.0446 (8) | |
C9 | 0.4877 (3) | 0.6449 (3) | 0.2585 (3) | 0.0468 (8) | |
C10 | 0.5095 (4) | 0.7521 (4) | 0.3783 (3) | 0.0604 (9) | |
H10 | 0.5604 | 0.8422 | 0.3948 | 0.072* | |
C11 | 0.4526 (4) | 0.7180 (4) | 0.4694 (4) | 0.0660 (10) | |
H11 | 0.4671 | 0.7864 | 0.5508 | 0.079* | |
C12 | 0.3733 (4) | 0.5841 (4) | 0.4454 (4) | 0.0637 (10) | |
H12 | 0.3338 | 0.5668 | 0.5097 | 0.076* | |
C13 | 0.3525 (3) | 0.4777 (4) | 0.3292 (3) | 0.0551 (9) | |
H13 | 0.3020 | 0.3876 | 0.3135 | 0.066* | |
C14 | 0.0140 (3) | 0.5264 (3) | 0.5713 (3) | 0.0413 (7) | |
C15 | 0.0878 (3) | 0.5416 (3) | 0.7811 (3) | 0.0456 (8) | |
C16 | 0.0232 (3) | 0.6517 (3) | 0.7687 (3) | 0.0473 (8) | |
C17 | 0.0148 (4) | 0.7520 (4) | 0.8792 (4) | 0.0612 (10) | |
H17 | −0.0283 | 0.8252 | 0.8715 | 0.073* | |
C18 | 0.0719 (4) | 0.7413 (4) | 1.0015 (4) | 0.0678 (11) | |
H18 | 0.0675 | 0.8079 | 1.0776 | 0.081* | |
C19 | 0.1369 (4) | 0.6304 (4) | 1.0125 (4) | 0.0678 (11) | |
H19 | 0.1758 | 0.6259 | 1.0962 | 0.081* | |
C20 | 0.1445 (3) | 0.5300 (4) | 0.9045 (3) | 0.0580 (9) | |
H20 | 0.1861 | 0.4560 | 0.9126 | 0.070* | |
C21 | 0.1332 (3) | 0.3328 (3) | 0.6268 (3) | 0.0511 (8) | |
H21A | 0.2264 | 0.3508 | 0.6857 | 0.061* | |
H21B | 0.1399 | 0.3066 | 0.5367 | 0.061* | |
C22 | 0.0419 (3) | 0.2130 (3) | 0.6430 (3) | 0.0448 (8) | |
C23 | −0.1013 (3) | 0.1973 (4) | 0.6203 (3) | 0.0555 (9) | |
H23 | −0.1450 | 0.2643 | 0.5966 | 0.067* | |
C24 | −0.1775 (4) | 0.0819 (4) | 0.6332 (4) | 0.0681 (11) | |
H24 | −0.2732 | 0.0739 | 0.6181 | 0.082* | |
C25 | 0.0122 (5) | −0.0037 (4) | 0.6856 (4) | 0.0721 (11) | |
H25 | 0.0527 | −0.0737 | 0.7067 | 0.087* | |
C26 | 0.0983 (4) | 0.1086 (3) | 0.6771 (3) | 0.0538 (9) | |
H26 | 0.1939 | 0.1143 | 0.6942 | 0.065* | |
N1 | 0.5940 (3) | 0.0277 (3) | 0.2252 (3) | 0.0631 (8) | |
N2 | 0.4121 (3) | 0.4319 (2) | 0.1107 (2) | 0.0440 (6) | |
N3 | 0.5341 (3) | 0.6494 (3) | 0.1504 (2) | 0.0491 (7) | |
N4 | −0.0216 (3) | 0.6393 (3) | 0.6362 (2) | 0.0480 (7) | |
N5 | 0.0810 (3) | 0.4621 (2) | 0.6554 (2) | 0.0454 (7) | |
N6 | −0.1243 (4) | −0.0196 (3) | 0.6660 (3) | 0.0762 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.070 (3) | 0.042 (2) | 0.083 (3) | 0.0096 (19) | 0.016 (2) | 0.0215 (19) |
C2 | 0.045 (2) | 0.045 (2) | 0.075 (2) | 0.0044 (16) | 0.0062 (17) | 0.0237 (18) |
C3 | 0.0409 (18) | 0.0437 (18) | 0.0431 (17) | 0.0078 (15) | 0.0110 (13) | 0.0152 (14) |
C4 | 0.045 (2) | 0.0462 (19) | 0.068 (2) | 0.0060 (16) | 0.0105 (16) | 0.0233 (17) |
C5 | 0.043 (2) | 0.062 (2) | 0.078 (3) | 0.0157 (18) | 0.0138 (17) | 0.027 (2) |
C6 | 0.0442 (19) | 0.0454 (19) | 0.0529 (19) | 0.0010 (15) | −0.0001 (14) | 0.0190 (16) |
C7 | 0.0342 (16) | 0.0380 (17) | 0.0506 (17) | 0.0125 (14) | 0.0018 (13) | 0.0182 (15) |
C8 | 0.0327 (16) | 0.0485 (19) | 0.057 (2) | 0.0176 (15) | 0.0050 (14) | 0.0255 (16) |
C9 | 0.0360 (17) | 0.051 (2) | 0.055 (2) | 0.0221 (15) | 0.0066 (14) | 0.0187 (16) |
C10 | 0.061 (2) | 0.052 (2) | 0.063 (2) | 0.0231 (18) | 0.0131 (18) | 0.0111 (18) |
C11 | 0.062 (2) | 0.079 (3) | 0.053 (2) | 0.032 (2) | 0.0117 (18) | 0.011 (2) |
C12 | 0.053 (2) | 0.083 (3) | 0.059 (2) | 0.028 (2) | 0.0145 (17) | 0.026 (2) |
C13 | 0.0417 (19) | 0.063 (2) | 0.068 (2) | 0.0195 (17) | 0.0081 (16) | 0.0338 (19) |
C14 | 0.0355 (17) | 0.0366 (16) | 0.0543 (17) | 0.0120 (14) | 0.0063 (14) | 0.0220 (15) |
C15 | 0.0358 (17) | 0.0479 (19) | 0.052 (2) | 0.0072 (15) | 0.0065 (14) | 0.0210 (16) |
C16 | 0.0427 (18) | 0.0427 (18) | 0.053 (2) | 0.0018 (15) | 0.0116 (14) | 0.0156 (16) |
C17 | 0.062 (2) | 0.052 (2) | 0.068 (2) | 0.0067 (18) | 0.0186 (19) | 0.0195 (19) |
C18 | 0.069 (3) | 0.069 (3) | 0.057 (2) | 0.004 (2) | 0.0188 (19) | 0.013 (2) |
C19 | 0.059 (2) | 0.083 (3) | 0.054 (2) | 0.003 (2) | 0.0057 (17) | 0.025 (2) |
C20 | 0.044 (2) | 0.072 (2) | 0.058 (2) | 0.0114 (18) | 0.0055 (16) | 0.0310 (19) |
C21 | 0.0426 (19) | 0.056 (2) | 0.063 (2) | 0.0263 (16) | 0.0109 (15) | 0.0278 (17) |
C22 | 0.0495 (19) | 0.0436 (18) | 0.0411 (17) | 0.0201 (15) | 0.0067 (14) | 0.0135 (14) |
C23 | 0.047 (2) | 0.052 (2) | 0.066 (2) | 0.0186 (17) | 0.0061 (16) | 0.0213 (17) |
C24 | 0.058 (2) | 0.059 (2) | 0.083 (3) | 0.014 (2) | 0.020 (2) | 0.017 (2) |
C25 | 0.093 (3) | 0.052 (2) | 0.092 (3) | 0.037 (2) | 0.038 (2) | 0.034 (2) |
C26 | 0.060 (2) | 0.050 (2) | 0.059 (2) | 0.0294 (18) | 0.0170 (16) | 0.0211 (17) |
N1 | 0.062 (2) | 0.0549 (19) | 0.078 (2) | 0.0198 (16) | 0.0182 (16) | 0.0281 (16) |
N2 | 0.0424 (15) | 0.0386 (14) | 0.0480 (15) | 0.0101 (12) | 0.0032 (11) | 0.0167 (12) |
N3 | 0.0462 (16) | 0.0450 (16) | 0.0546 (17) | 0.0136 (13) | 0.0069 (13) | 0.0182 (14) |
N4 | 0.0518 (17) | 0.0404 (15) | 0.0551 (17) | 0.0143 (13) | 0.0117 (13) | 0.0214 (13) |
N5 | 0.0400 (15) | 0.0429 (15) | 0.0556 (17) | 0.0157 (12) | 0.0072 (12) | 0.0217 (13) |
N6 | 0.088 (3) | 0.053 (2) | 0.099 (3) | 0.0219 (19) | 0.039 (2) | 0.0302 (18) |
C1—N1 | 1.323 (4) | C14—N4 | 1.317 (4) |
C1—C2 | 1.376 (5) | C14—N5 | 1.387 (4) |
C1—H1 | 0.9300 | C14—C14ii | 1.448 (6) |
C2—C3 | 1.369 (4) | C15—N5 | 1.369 (4) |
C2—H2 | 0.9300 | C15—C20 | 1.390 (4) |
C3—C4 | 1.372 (4) | C15—C16 | 1.399 (4) |
C3—C6 | 1.513 (4) | C16—C17 | 1.377 (4) |
C4—C5 | 1.389 (5) | C16—N4 | 1.383 (4) |
C4—H4 | 0.9300 | C17—C18 | 1.376 (5) |
C5—N1 | 1.314 (4) | C17—H17 | 0.9300 |
C5—H5 | 0.9300 | C18—C19 | 1.406 (5) |
C6—N2 | 1.466 (4) | C18—H18 | 0.9300 |
C6—H6A | 0.9700 | C19—C20 | 1.355 (5) |
C6—H6B | 0.9700 | C19—H19 | 0.9300 |
C7—N3 | 1.316 (4) | C20—H20 | 0.9300 |
C7—N2 | 1.372 (4) | C21—N5 | 1.468 (4) |
C7—C7i | 1.464 (6) | C21—C22 | 1.495 (4) |
C8—C9 | 1.386 (4) | C21—H21A | 0.9700 |
C8—C13 | 1.388 (4) | C21—H21B | 0.9700 |
C8—N2 | 1.389 (4) | C22—C26 | 1.378 (4) |
C9—N3 | 1.380 (4) | C22—C23 | 1.387 (4) |
C9—C10 | 1.399 (4) | C23—C24 | 1.368 (5) |
C10—C11 | 1.360 (5) | C23—H23 | 0.9300 |
C10—H10 | 0.9300 | C24—N6 | 1.330 (5) |
C11—C12 | 1.397 (5) | C24—H24 | 0.9300 |
C11—H11 | 0.9300 | C25—N6 | 1.324 (5) |
C12—C13 | 1.370 (5) | C25—C26 | 1.370 (5) |
C12—H12 | 0.9300 | C25—H25 | 0.9300 |
C13—H13 | 0.9300 | C26—H26 | 0.9300 |
N1—C1—C2 | 124.1 (3) | C20—C15—C16 | 121.3 (3) |
N1—C1—H1 | 118.0 | C17—C16—N4 | 130.2 (3) |
C2—C1—H1 | 118.0 | C17—C16—C15 | 120.5 (3) |
C3—C2—C1 | 119.6 (3) | N4—C16—C15 | 109.3 (3) |
C3—C2—H2 | 120.2 | C18—C17—C16 | 118.2 (4) |
C1—C2—H2 | 120.2 | C18—C17—H17 | 120.9 |
C2—C3—C4 | 117.4 (3) | C16—C17—H17 | 120.9 |
C2—C3—C6 | 120.4 (3) | C17—C18—C19 | 120.6 (3) |
C4—C3—C6 | 122.1 (3) | C17—C18—H18 | 119.7 |
C3—C4—C5 | 118.4 (3) | C19—C18—H18 | 119.7 |
C3—C4—H4 | 120.8 | C20—C19—C18 | 121.8 (4) |
C5—C4—H4 | 120.8 | C20—C19—H19 | 119.1 |
N1—C5—C4 | 124.8 (3) | C18—C19—H19 | 119.1 |
N1—C5—H5 | 117.6 | C19—C20—C15 | 117.5 (4) |
C4—C5—H5 | 117.6 | C19—C20—H20 | 121.2 |
N2—C6—C3 | 113.4 (2) | C15—C20—H20 | 121.2 |
N2—C6—H6A | 108.9 | N5—C21—C22 | 112.8 (2) |
C3—C6—H6A | 108.9 | N5—C21—H21A | 109.0 |
N2—C6—H6B | 108.9 | C22—C21—H21A | 109.0 |
C3—C6—H6B | 108.9 | N5—C21—H21B | 109.0 |
H6A—C6—H6B | 107.7 | C22—C21—H21B | 109.0 |
N3—C7—N2 | 113.0 (3) | H21A—C21—H21B | 107.8 |
N3—C7—C7i | 123.4 (3) | C26—C22—C23 | 116.7 (3) |
N2—C7—C7i | 123.6 (3) | C26—C22—C21 | 120.1 (3) |
C9—C8—C13 | 122.5 (3) | C23—C22—C21 | 123.1 (3) |
C9—C8—N2 | 105.6 (3) | C24—C23—C22 | 119.2 (3) |
C13—C8—N2 | 132.0 (3) | C24—C23—H23 | 120.4 |
N3—C9—C8 | 110.5 (3) | C22—C23—H23 | 120.4 |
N3—C9—C10 | 129.0 (3) | N6—C24—C23 | 124.7 (4) |
C8—C9—C10 | 120.5 (3) | N6—C24—H24 | 117.7 |
C11—C10—C9 | 116.7 (3) | C23—C24—H24 | 117.7 |
C11—C10—H10 | 121.6 | N6—C25—C26 | 124.8 (3) |
C9—C10—H10 | 121.6 | N6—C25—H25 | 117.6 |
C10—C11—C12 | 122.5 (3) | C26—C25—H25 | 117.6 |
C10—C11—H11 | 118.7 | C25—C26—C22 | 119.4 (3) |
C12—C11—H11 | 118.7 | C25—C26—H26 | 120.3 |
C13—C12—C11 | 121.4 (3) | C22—C26—H26 | 120.3 |
C13—C12—H12 | 119.3 | C5—N1—C1 | 115.6 (3) |
C11—C12—H12 | 119.3 | C7—N2—C8 | 106.0 (2) |
C12—C13—C8 | 116.4 (3) | C7—N2—C6 | 131.4 (3) |
C12—C13—H13 | 121.8 | C8—N2—C6 | 122.4 (3) |
C8—C13—H13 | 121.8 | C7—N3—C9 | 105.0 (3) |
N4—C14—N5 | 112.1 (3) | C14—N4—C16 | 105.8 (3) |
N4—C14—C14ii | 124.4 (3) | C15—N5—C14 | 106.3 (3) |
N5—C14—C14ii | 123.4 (3) | C15—N5—C21 | 122.8 (3) |
N5—C15—C20 | 132.3 (3) | C14—N5—C21 | 130.8 (3) |
N5—C15—C16 | 106.5 (3) | C25—N6—C24 | 115.3 (3) |
N1—C1—C2—C3 | 1.5 (6) | N6—C25—C26—C22 | −1.5 (6) |
C1—C2—C3—C4 | −0.8 (5) | C23—C22—C26—C25 | 0.6 (5) |
C1—C2—C3—C6 | 176.9 (3) | C21—C22—C26—C25 | −177.1 (3) |
C2—C3—C4—C5 | 0.2 (5) | C4—C5—N1—C1 | 0.9 (5) |
C6—C3—C4—C5 | −177.5 (3) | C2—C1—N1—C5 | −1.5 (6) |
C3—C4—C5—N1 | −0.3 (5) | N3—C7—N2—C8 | 0.3 (3) |
C2—C3—C6—N2 | 158.5 (3) | C7i—C7—N2—C8 | −179.1 (3) |
C4—C3—C6—N2 | −23.9 (4) | N3—C7—N2—C6 | −174.3 (3) |
C13—C8—C9—N3 | 179.5 (3) | C7i—C7—N2—C6 | 6.3 (5) |
N2—C8—C9—N3 | 0.9 (3) | C9—C8—N2—C7 | −0.7 (3) |
C13—C8—C9—C10 | −0.2 (5) | C13—C8—N2—C7 | −179.1 (3) |
N2—C8—C9—C10 | −178.8 (3) | C9—C8—N2—C6 | 174.5 (2) |
N3—C9—C10—C11 | −179.2 (3) | C13—C8—N2—C6 | −4.0 (5) |
C8—C9—C10—C11 | 0.4 (5) | C3—C6—N2—C7 | 101.2 (3) |
C9—C10—C11—C12 | −1.4 (5) | C3—C6—N2—C8 | −72.6 (4) |
C10—C11—C12—C13 | 2.2 (5) | N2—C7—N3—C9 | 0.3 (3) |
C11—C12—C13—C8 | −1.9 (5) | C7i—C7—N3—C9 | 179.7 (3) |
C9—C8—C13—C12 | 0.9 (5) | C8—C9—N3—C7 | −0.8 (3) |
N2—C8—C13—C12 | 179.1 (3) | C10—C9—N3—C7 | 178.9 (3) |
N5—C15—C16—C17 | −179.1 (3) | N5—C14—N4—C16 | 0.1 (3) |
C20—C15—C16—C17 | 0.3 (5) | C14ii—C14—N4—C16 | 179.6 (3) |
N5—C15—C16—N4 | −0.4 (3) | C17—C16—N4—C14 | 178.8 (3) |
C20—C15—C16—N4 | 179.0 (3) | C15—C16—N4—C14 | 0.2 (3) |
N4—C16—C17—C18 | −178.2 (3) | C20—C15—N5—C14 | −178.9 (3) |
C15—C16—C17—C18 | 0.2 (5) | C16—C15—N5—C14 | 0.4 (3) |
C16—C17—C18—C19 | 0.0 (5) | C20—C15—N5—C21 | 3.2 (5) |
C17—C18—C19—C20 | −0.8 (6) | C16—C15—N5—C21 | −177.5 (3) |
C18—C19—C20—C15 | 1.2 (5) | N4—C14—N5—C15 | −0.4 (3) |
N5—C15—C20—C19 | 178.3 (3) | C14ii—C14—N5—C15 | −179.9 (3) |
C16—C15—C20—C19 | −1.0 (5) | N4—C14—N5—C21 | 177.3 (3) |
N5—C21—C22—C26 | −151.8 (3) | C14ii—C14—N5—C21 | −2.2 (6) |
N5—C21—C22—C23 | 30.8 (4) | C22—C21—N5—C15 | 72.9 (4) |
C26—C22—C23—C24 | 0.3 (5) | C22—C21—N5—C14 | −104.5 (3) |
C21—C22—C23—C24 | 177.8 (3) | C26—C25—N6—C24 | 1.4 (6) |
C22—C23—C24—N6 | −0.4 (6) | C23—C24—N6—C25 | −0.4 (6) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+1, −z+1. |
[HgCl2(C26H20N6)] | F(000) = 1328 |
Mr = 687.97 | Dx = 1.862 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C2yc | Cell parameters from 2207 reflections |
a = 29.641 (15) Å | θ = 2.8–24.7° |
b = 4.953 (2) Å | µ = 6.52 mm−1 |
c = 16.932 (8) Å | T = 298 K |
β = 99.236 (11)° | Plan, colourless |
V = 2454 (2) Å3 | 0.20 × 0.10 × 0.04 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 2293 independent reflections |
Radiation source: fine-focus sealed tube | 1745 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
phi and ω scans | θmax = 25.6°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | h = −36→29 |
Tmin = 0.356, Tmax = 0.781 | k = −6→5 |
6064 measured reflections | l = −19→20 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.076 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.033P)2] where P = (Fo2 + 2Fc2)/3 |
2293 reflections | (Δ/σ)max = 0.001 |
159 parameters | Δρmax = 1.06 e Å−3 |
0 restraints | Δρmin = −0.75 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.04608 (19) | 0.6141 (13) | 0.3915 (4) | 0.0735 (17) | |
H1 | 0.0153 | 0.6350 | 0.3954 | 0.088* | |
C2 | 0.0770 (2) | 0.7553 (10) | 0.4436 (4) | 0.0680 (16) | |
H2 | 0.0672 | 0.8723 | 0.4804 | 0.082* | |
C3 | 0.12272 (17) | 0.7234 (9) | 0.4415 (3) | 0.0444 (12) | |
C4 | 0.13442 (16) | 0.5511 (11) | 0.3852 (3) | 0.0565 (13) | |
H4 | 0.1650 | 0.5216 | 0.3816 | 0.068* | |
C5 | 0.10072 (19) | 0.4217 (13) | 0.3341 (3) | 0.0654 (15) | |
H5 | 0.1095 | 0.3071 | 0.2958 | 0.078* | |
C6 | 0.15835 (16) | 0.8771 (9) | 0.4984 (3) | 0.0478 (12) | |
H6A | 0.1718 | 1.0157 | 0.4691 | 0.057* | |
H6B | 0.1438 | 0.9652 | 0.5389 | 0.057* | |
C7 | 0.23906 (17) | 0.6681 (9) | 0.5277 (2) | 0.0403 (10) | |
C8 | 0.18701 (16) | 0.5128 (9) | 0.5949 (2) | 0.0423 (11) | |
C9 | 0.22823 (17) | 0.3793 (9) | 0.6164 (3) | 0.0442 (12) | |
C10 | 0.2318 (2) | 0.1755 (10) | 0.6743 (3) | 0.0541 (13) | |
H10 | 0.2590 | 0.0818 | 0.6897 | 0.065* | |
C11 | 0.1939 (2) | 0.1202 (11) | 0.7073 (3) | 0.0604 (15) | |
H11 | 0.1953 | −0.0150 | 0.7457 | 0.072* | |
C12 | 0.1531 (2) | 0.2589 (10) | 0.6854 (3) | 0.0577 (15) | |
H12 | 0.1281 | 0.2143 | 0.7097 | 0.069* | |
C13 | 0.14858 (17) | 0.4585 (11) | 0.6292 (3) | 0.0524 (12) | |
H13 | 0.1214 | 0.5525 | 0.6148 | 0.063* | |
Cl1 | 0.04580 (5) | 0.0778 (4) | 0.15364 (10) | 0.0924 (5) | |
Hg1 | 0.0000 | 0.19383 (7) | 0.2500 | 0.07134 (16) | |
N1 | 0.05643 (14) | 0.4501 (10) | 0.3360 (2) | 0.0566 (11) | |
N2 | 0.19419 (14) | 0.6973 (7) | 0.5371 (2) | 0.0426 (9) | |
N3 | 0.26075 (13) | 0.4803 (8) | 0.5749 (2) | 0.0458 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.030 (3) | 0.091 (5) | 0.095 (4) | 0.013 (3) | −0.001 (3) | −0.006 (4) |
C2 | 0.046 (4) | 0.078 (4) | 0.080 (4) | 0.015 (3) | 0.007 (3) | −0.021 (3) |
C3 | 0.042 (3) | 0.047 (3) | 0.043 (3) | 0.006 (2) | 0.003 (2) | 0.009 (2) |
C4 | 0.032 (3) | 0.083 (4) | 0.054 (3) | −0.001 (3) | 0.009 (2) | −0.015 (3) |
C5 | 0.050 (4) | 0.092 (4) | 0.054 (3) | −0.001 (3) | 0.008 (3) | −0.017 (3) |
C6 | 0.047 (3) | 0.039 (3) | 0.056 (3) | 0.005 (2) | 0.003 (2) | −0.001 (2) |
C7 | 0.046 (3) | 0.037 (3) | 0.036 (2) | −0.003 (2) | 0.001 (2) | −0.009 (2) |
C8 | 0.051 (3) | 0.040 (3) | 0.035 (2) | −0.006 (2) | 0.002 (2) | −0.010 (2) |
C9 | 0.052 (3) | 0.037 (3) | 0.040 (2) | −0.006 (2) | −0.001 (2) | −0.004 (2) |
C10 | 0.062 (4) | 0.048 (3) | 0.049 (3) | −0.001 (3) | −0.002 (3) | 0.004 (3) |
C11 | 0.075 (4) | 0.055 (4) | 0.049 (3) | −0.012 (3) | 0.001 (3) | 0.004 (2) |
C12 | 0.064 (4) | 0.061 (4) | 0.051 (3) | −0.019 (3) | 0.015 (3) | −0.007 (3) |
C13 | 0.052 (3) | 0.051 (3) | 0.053 (3) | −0.005 (3) | 0.008 (2) | −0.008 (3) |
Cl1 | 0.0523 (10) | 0.1269 (14) | 0.0996 (11) | −0.0066 (9) | 0.0175 (8) | −0.0222 (11) |
Hg1 | 0.0383 (2) | 0.1028 (3) | 0.0689 (2) | 0.000 | −0.00357 (14) | 0.000 |
N1 | 0.037 (2) | 0.076 (3) | 0.054 (2) | 0.002 (2) | −0.0026 (19) | 0.000 (2) |
N2 | 0.044 (2) | 0.039 (2) | 0.042 (2) | −0.0003 (19) | −0.0011 (17) | −0.0023 (18) |
N3 | 0.045 (2) | 0.047 (3) | 0.042 (2) | −0.001 (2) | −0.0022 (18) | 0.0004 (19) |
C1—N1 | 1.316 (7) | C8—N2 | 1.380 (6) |
C1—C2 | 1.359 (8) | C8—C9 | 1.386 (6) |
C1—H1 | 0.9300 | C8—C13 | 1.386 (6) |
C2—C3 | 1.371 (7) | C9—N3 | 1.374 (6) |
C2—H2 | 0.9300 | C9—C10 | 1.400 (7) |
C3—C4 | 1.365 (7) | C10—C11 | 1.361 (8) |
C3—C6 | 1.516 (7) | C10—H10 | 0.9300 |
C4—C5 | 1.371 (7) | C11—C12 | 1.388 (8) |
C4—H4 | 0.9300 | C11—H11 | 0.9300 |
C5—N1 | 1.326 (6) | C12—C13 | 1.363 (7) |
C5—H5 | 0.9300 | C12—H12 | 0.9300 |
C6—N2 | 1.458 (6) | C13—H13 | 0.9300 |
C6—H6A | 0.9700 | Hg1—N1 | 2.397 (4) |
C6—H6B | 0.9700 | Hg1—N1ii | 2.397 (4) |
C7—N3 | 1.324 (5) | Hg1—Cl1 | 2.3553 (18) |
C7—N2 | 1.372 (6) | Hg1—Cl1ii | 2.3553 (18) |
C7—C7i | 1.468 (10) | ||
N1—C1—C2 | 124.9 (5) | N3—C9—C10 | 129.8 (5) |
N1—C1—H1 | 117.6 | C8—C9—C10 | 119.5 (5) |
C2—C1—H1 | 117.6 | C11—C10—C9 | 117.2 (5) |
C1—C2—C3 | 119.3 (5) | C11—C10—H10 | 121.4 |
C1—C2—H2 | 120.3 | C9—C10—H10 | 121.4 |
C3—C2—H2 | 120.3 | C10—C11—C12 | 122.2 (5) |
C4—C3—C2 | 117.0 (5) | C10—C11—H11 | 118.9 |
C4—C3—C6 | 122.0 (4) | C12—C11—H11 | 118.9 |
C2—C3—C6 | 121.1 (4) | C13—C12—C11 | 122.0 (5) |
C3—C4—C5 | 119.5 (5) | C13—C12—H12 | 119.0 |
C3—C4—H4 | 120.3 | C11—C12—H12 | 119.0 |
C5—C4—H4 | 120.3 | C12—C13—C8 | 116.0 (5) |
N1—C5—C4 | 124.0 (5) | C12—C13—H13 | 122.0 |
N1—C5—H5 | 118.0 | C8—C13—H13 | 122.0 |
C4—C5—H5 | 118.0 | N1—Hg1—N1ii | 116.0 (2) |
N2—C6—C3 | 111.2 (4) | Cl1—Hg1—N1 | 97.25 (12) |
N2—C6—H6A | 109.4 | Cl1ii—Hg1—N1 | 97.60 (11) |
C3—C6—H6A | 109.4 | Cl1—Hg1—N1ii | 97.60 (11) |
N2—C6—H6B | 109.4 | Cl1ii—Hg1—N1ii | 97.25 (12) |
C3—C6—H6B | 109.4 | Cl1—Hg1—Cl1ii | 151.74 (10) |
H6A—C6—H6B | 108.0 | C1—N1—C5 | 115.3 (4) |
N3—C7—N2 | 112.9 (4) | C1—N1—Hg1 | 122.7 (3) |
N3—C7—C7i | 123.5 (6) | C5—N1—Hg1 | 121.8 (4) |
N2—C7—C7i | 123.5 (5) | C7—N2—C8 | 106.0 (4) |
N2—C8—C9 | 105.8 (4) | C7—N2—C6 | 131.5 (4) |
N2—C8—C13 | 131.1 (5) | C8—N2—C6 | 122.6 (4) |
C9—C8—C13 | 123.1 (5) | C7—N3—C9 | 104.6 (4) |
N3—C9—C8 | 110.7 (4) | ||
N1—C1—C2—C3 | −2.1 (9) | C4—C5—N1—Hg1 | −175.9 (4) |
C1—C2—C3—C4 | 0.9 (8) | Cl1—Hg1—N1—C1 | 164.5 (4) |
C1—C2—C3—C6 | 179.9 (5) | Cl1ii—Hg1—N1—C1 | −39.6 (4) |
C2—C3—C4—C5 | 0.4 (8) | N1ii—Hg1—N1—C1 | 62.4 (4) |
C6—C3—C4—C5 | −178.6 (5) | Cl1—Hg1—N1—C5 | −20.1 (4) |
C3—C4—C5—N1 | −0.8 (9) | Cl1ii—Hg1—N1—C5 | 135.8 (4) |
C4—C3—C6—N2 | −50.0 (6) | N1ii—Hg1—N1—C5 | −122.3 (4) |
C2—C3—C6—N2 | 131.0 (5) | N3—C7—N2—C8 | −0.1 (5) |
N2—C8—C9—N3 | 1.3 (5) | C7i—C7—N2—C8 | −178.9 (5) |
C13—C8—C9—N3 | −177.8 (4) | N3—C7—N2—C6 | 179.7 (4) |
N2—C8—C9—C10 | −179.6 (4) | C7i—C7—N2—C6 | 0.9 (8) |
C13—C8—C9—C10 | 1.3 (7) | C9—C8—N2—C7 | −0.8 (4) |
N3—C9—C10—C11 | 178.5 (4) | C13—C8—N2—C7 | 178.3 (4) |
C8—C9—C10—C11 | −0.4 (7) | C9—C8—N2—C6 | 179.4 (4) |
C9—C10—C11—C12 | −0.3 (8) | C13—C8—N2—C6 | −1.5 (7) |
C10—C11—C12—C13 | 0.3 (8) | C3—C6—N2—C7 | 108.6 (5) |
C11—C12—C13—C8 | 0.5 (7) | C3—C6—N2—C8 | −71.6 (5) |
N2—C8—C13—C12 | 179.8 (4) | N2—C7—N3—C9 | 0.9 (5) |
C9—C8—C13—C12 | −1.3 (7) | C7i—C7—N3—C9 | 179.7 (5) |
C2—C1—N1—C5 | 1.7 (9) | C8—C9—N3—C7 | −1.4 (5) |
C2—C1—N1—Hg1 | 177.3 (5) | C10—C9—N3—C7 | 179.7 (4) |
C4—C5—N1—C1 | −0.2 (8) |
Symmetry codes: (i) −x+1/2, −y+3/2, −z+1; (ii) −x, y, −z+1/2. |
[HgBr2(C26H20N6)] | F(000) = 1472 |
Mr = 776.89 | Dx = 2.037 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -c2yc | Cell parameters from 3227 reflections |
a = 24.494 (8) Å | θ = 2.4–25.9° |
b = 6.006 (2) Å | µ = 9.26 mm−1 |
c = 17.306 (6) Å | T = 298 K |
β = 95.796 (4)° | Block, colourless |
V = 2532.8 (15) Å3 | 0.23 × 0.18 × 0.10 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 2387 independent reflections |
Radiation source: fine-focus sealed tube | 2101 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
phi and ω scans | θmax = 25.6°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | h = −29→22 |
Tmin = 0.225, Tmax = 0.458 | k = −5→7 |
6393 measured reflections | l = −21→20 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.085 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0537P)2] where P = (Fo2 + 2Fc2)/3 |
2387 reflections | (Δ/σ)max = 0.001 |
159 parameters | Δρmax = 1.05 e Å−3 |
0 restraints | Δρmin = −1.35 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.0507 (2) | 0.5005 (10) | 0.9059 (3) | 0.0543 (15) | |
H1 | 0.0291 | 0.6031 | 0.9292 | 0.065* | |
C2 | 0.0822 (2) | 0.3553 (10) | 0.9522 (3) | 0.0505 (14) | |
H2 | 0.0819 | 0.3599 | 1.0058 | 0.061* | |
C3 | 0.1150 (2) | 0.2002 (8) | 0.9183 (3) | 0.0377 (11) | |
C4 | 0.1135 (2) | 0.2007 (9) | 0.8392 (3) | 0.0462 (13) | |
H4 | 0.1346 | 0.0994 | 0.8144 | 0.055* | |
C5 | 0.0808 (3) | 0.3517 (10) | 0.7964 (3) | 0.0513 (14) | |
H5 | 0.0805 | 0.3497 | 0.7426 | 0.062* | |
C6 | 0.1503 (2) | 0.0404 (8) | 0.9690 (3) | 0.0401 (11) | |
H6A | 0.1509 | 0.0872 | 1.0227 | 0.048* | |
H6B | 0.1339 | −0.1067 | 0.9646 | 0.048* | |
C7 | 0.2518 (2) | 0.1531 (8) | 0.9745 (3) | 0.0353 (10) | |
C8 | 0.2264 (2) | −0.1381 (8) | 0.9033 (3) | 0.0371 (11) | |
C9 | 0.2823 (2) | −0.1007 (8) | 0.9044 (3) | 0.0385 (11) | |
C10 | 0.3151 (3) | −0.2426 (8) | 0.8651 (3) | 0.0463 (13) | |
H10 | 0.3527 | −0.2192 | 0.8657 | 0.056* | |
C11 | 0.2895 (3) | −0.4189 (9) | 0.8256 (3) | 0.0534 (15) | |
H11 | 0.3103 | −0.5175 | 0.7992 | 0.064* | |
C12 | 0.2334 (3) | −0.4529 (9) | 0.8241 (3) | 0.0542 (15) | |
H12 | 0.2176 | −0.5731 | 0.7963 | 0.065* | |
C13 | 0.2000 (3) | −0.3131 (8) | 0.8627 (3) | 0.0486 (13) | |
H13 | 0.1623 | −0.3354 | 0.8614 | 0.058* | |
Hg1 | 0.0000 | 0.77841 (5) | 0.7500 | 0.04575 (14) | |
Br1 | −0.05808 (4) | 0.90727 (16) | 0.84956 (4) | 0.0981 (3) | |
N1 | 0.04965 (17) | 0.5005 (8) | 0.8282 (2) | 0.0464 (11) | |
N2 | 0.20649 (16) | 0.0267 (6) | 0.9488 (2) | 0.0353 (9) | |
N3 | 0.29770 (18) | 0.0830 (6) | 0.9497 (2) | 0.0401 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.041 (3) | 0.074 (4) | 0.049 (3) | 0.021 (3) | 0.008 (3) | −0.004 (3) |
C2 | 0.042 (3) | 0.071 (3) | 0.040 (3) | 0.015 (3) | 0.008 (2) | 0.002 (2) |
C3 | 0.024 (3) | 0.043 (2) | 0.046 (3) | −0.004 (2) | 0.002 (2) | −0.001 (2) |
C4 | 0.045 (3) | 0.049 (3) | 0.045 (3) | 0.010 (2) | 0.002 (2) | −0.012 (2) |
C5 | 0.056 (4) | 0.059 (3) | 0.038 (3) | 0.012 (3) | −0.003 (3) | −0.007 (2) |
C6 | 0.033 (3) | 0.041 (2) | 0.047 (3) | −0.001 (2) | 0.008 (2) | 0.003 (2) |
C7 | 0.032 (3) | 0.039 (2) | 0.034 (2) | 0.005 (2) | 0.000 (2) | 0.0017 (19) |
C8 | 0.039 (3) | 0.037 (2) | 0.035 (2) | 0.005 (2) | 0.000 (2) | 0.0017 (19) |
C9 | 0.044 (3) | 0.040 (3) | 0.031 (2) | 0.011 (2) | 0.001 (2) | 0.0042 (19) |
C10 | 0.045 (3) | 0.051 (3) | 0.045 (3) | 0.014 (2) | 0.011 (2) | 0.006 (2) |
C11 | 0.075 (5) | 0.045 (3) | 0.042 (3) | 0.016 (3) | 0.016 (3) | −0.002 (2) |
C12 | 0.073 (5) | 0.043 (3) | 0.047 (3) | 0.002 (3) | 0.008 (3) | −0.009 (2) |
C13 | 0.051 (4) | 0.045 (3) | 0.050 (3) | −0.003 (3) | 0.006 (3) | −0.007 (2) |
Hg1 | 0.0374 (2) | 0.0554 (2) | 0.04453 (19) | 0.000 | 0.00467 (12) | 0.000 |
Br1 | 0.1052 (7) | 0.1223 (7) | 0.0746 (5) | 0.0701 (6) | 0.0467 (4) | 0.0372 (4) |
N1 | 0.030 (3) | 0.067 (3) | 0.042 (2) | 0.010 (2) | −0.0012 (19) | −0.007 (2) |
N2 | 0.027 (2) | 0.039 (2) | 0.040 (2) | 0.0041 (17) | 0.0032 (17) | −0.0009 (16) |
N3 | 0.034 (3) | 0.043 (2) | 0.044 (2) | 0.0037 (19) | 0.0030 (18) | −0.0030 (18) |
C1—N1 | 1.343 (6) | C8—C9 | 1.385 (7) |
C1—C2 | 1.370 (8) | C8—N2 | 1.385 (6) |
C1—H1 | 0.9300 | C8—C13 | 1.388 (8) |
C2—C3 | 1.396 (8) | C9—N3 | 1.384 (6) |
C2—H2 | 0.9300 | C9—C10 | 1.394 (7) |
C3—C4 | 1.365 (7) | C10—C11 | 1.377 (8) |
C3—C6 | 1.513 (7) | C10—H10 | 0.9300 |
C4—C5 | 1.376 (8) | C11—C12 | 1.387 (9) |
C4—H4 | 0.9300 | C11—H11 | 0.9300 |
C5—N1 | 1.330 (7) | C12—C13 | 1.390 (8) |
C5—H5 | 0.9300 | C12—H12 | 0.9300 |
C6—N2 | 1.455 (6) | C13—H13 | 0.9300 |
C6—H6A | 0.9700 | Hg1—N1ii | 2.400 (4) |
C6—H6B | 0.9700 | Hg1—N1 | 2.400 (4) |
C7—N3 | 1.313 (6) | Hg1—Br1 | 2.4671 (9) |
C7—N2 | 1.380 (6) | Hg1—Br1ii | 2.4671 (9) |
C7—C7i | 1.470 (10) | ||
N1—C1—C2 | 122.6 (5) | N3—C9—C10 | 128.7 (5) |
N1—C1—H1 | 118.7 | C8—C9—C10 | 120.8 (5) |
C2—C1—H1 | 118.7 | C11—C10—C9 | 117.1 (6) |
C1—C2—C3 | 119.5 (5) | C11—C10—H10 | 121.4 |
C1—C2—H2 | 120.2 | C9—C10—H10 | 121.4 |
C3—C2—H2 | 120.2 | C10—C11—C12 | 121.5 (5) |
C4—C3—C2 | 117.5 (5) | C10—C11—H11 | 119.2 |
C4—C3—C6 | 122.6 (5) | C12—C11—H11 | 119.2 |
C2—C3—C6 | 119.9 (5) | C11—C12—C13 | 122.2 (5) |
C3—C4—C5 | 119.7 (5) | C11—C12—H12 | 118.9 |
C3—C4—H4 | 120.2 | C13—C12—H12 | 118.9 |
C5—C4—H4 | 120.2 | C8—C13—C12 | 115.7 (6) |
N1—C5—C4 | 123.2 (5) | C8—C13—H13 | 122.2 |
N1—C5—H5 | 118.4 | C12—C13—H13 | 122.2 |
C4—C5—H5 | 118.4 | N1ii—Hg1—N1 | 91.9 (2) |
N2—C6—C3 | 113.4 (4) | N1ii—Hg1—Br1 | 108.46 (11) |
N2—C6—H6A | 108.9 | N1—Hg1—Br1 | 96.87 (10) |
C3—C6—H6A | 108.9 | N1ii—Hg1—Br1ii | 96.87 (10) |
N2—C6—H6B | 108.9 | N1—Hg1—Br1ii | 108.46 (11) |
C3—C6—H6B | 108.9 | Br1—Hg1—Br1ii | 143.43 (5) |
H6A—C6—H6B | 107.7 | C5—N1—C1 | 117.4 (5) |
N3—C7—N2 | 114.0 (4) | C5—N1—Hg1 | 120.9 (3) |
N3—C7—C7i | 123.7 (6) | C1—N1—Hg1 | 121.5 (3) |
N2—C7—C7i | 122.4 (6) | C7—N2—C8 | 104.9 (4) |
C9—C8—N2 | 106.4 (4) | C7—N2—C6 | 129.8 (4) |
C9—C8—C13 | 122.7 (5) | C8—N2—C6 | 125.0 (4) |
N2—C8—C13 | 131.0 (5) | C7—N3—C9 | 104.3 (4) |
N3—C9—C8 | 110.5 (4) | ||
N1—C1—C2—C3 | 0.1 (10) | C2—C1—N1—Hg1 | −174.5 (5) |
C1—C2—C3—C4 | −0.3 (9) | N1ii—Hg1—N1—C5 | 59.3 (4) |
C1—C2—C3—C6 | 179.5 (5) | Br1—Hg1—N1—C5 | 168.2 (4) |
C2—C3—C4—C5 | 0.4 (8) | Br1ii—Hg1—N1—C5 | −38.6 (5) |
C6—C3—C4—C5 | −179.4 (5) | N1ii—Hg1—N1—C1 | −126.3 (5) |
C3—C4—C5—N1 | −0.2 (10) | Br1—Hg1—N1—C1 | −17.4 (4) |
C4—C3—C6—N2 | 47.3 (7) | Br1ii—Hg1—N1—C1 | 135.9 (4) |
C2—C3—C6—N2 | −132.5 (5) | N3—C7—N2—C8 | −0.2 (5) |
N2—C8—C9—N3 | 0.2 (5) | C7i—C7—N2—C8 | −179.6 (5) |
C13—C8—C9—N3 | −179.5 (5) | N3—C7—N2—C6 | 174.1 (4) |
N2—C8—C9—C10 | 178.4 (4) | C7i—C7—N2—C6 | −5.3 (9) |
C13—C8—C9—C10 | −1.3 (7) | C9—C8—N2—C7 | 0.0 (5) |
N3—C9—C10—C11 | 178.1 (5) | C13—C8—N2—C7 | 179.7 (5) |
C8—C9—C10—C11 | 0.3 (7) | C9—C8—N2—C6 | −174.7 (4) |
C9—C10—C11—C12 | 0.6 (8) | C13—C8—N2—C6 | 5.0 (8) |
C10—C11—C12—C13 | −0.6 (9) | C3—C6—N2—C7 | 88.2 (6) |
C9—C8—C13—C12 | 1.3 (8) | C3—C6—N2—C8 | −98.4 (5) |
N2—C8—C13—C12 | −178.3 (5) | N2—C7—N3—C9 | 0.3 (5) |
C11—C12—C13—C8 | −0.4 (8) | C7i—C7—N3—C9 | 179.7 (6) |
C4—C5—N1—C1 | −0.1 (9) | C8—C9—N3—C7 | −0.3 (5) |
C4—C5—N1—Hg1 | 174.6 (5) | C10—C9—N3—C7 | −178.4 (5) |
C2—C1—N1—C5 | 0.1 (9) |
Symmetry codes: (i) −x+1/2, −y+1/2, −z+2; (ii) −x, y, −z+3/2. |
[HgI2(C26H20N6)] | F(000) = 1616 |
Mr = 870.87 | Dx = 2.156 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -c2yc | Cell parameters from 2156 reflections |
a = 25.339 (9) Å | θ = 2.6–21.8° |
b = 6.056 (2) Å | µ = 8.06 mm−1 |
c = 17.683 (6) Å | T = 298 K |
β = 98.619 (4)° | Block, colourless |
V = 2682.9 (16) Å3 | 0.16 × 0.12 × 0.09 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 2526 independent reflections |
Radiation source: fine-focus sealed tube | 1950 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
phi and ω scans | θmax = 25.6°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | h = −25→30 |
Tmin = 0.359, Tmax = 0.531 | k = −7→6 |
6723 measured reflections | l = −21→21 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.071 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0281P)2] where P = (Fo2 + 2Fc2)/3 |
2526 reflections | (Δ/σ)max < 0.001 |
159 parameters | Δρmax = 0.61 e Å−3 |
0 restraints | Δρmin = −1.19 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.0544 (3) | 0.4861 (12) | 0.9012 (4) | 0.070 (2) | |
H1 | 0.0324 | 0.5807 | 0.9237 | 0.084* | |
C2 | 0.0866 (2) | 0.3435 (13) | 0.9476 (4) | 0.070 (2) | |
H2 | 0.0868 | 0.3449 | 1.0002 | 0.084* | |
C3 | 0.1185 (2) | 0.1987 (9) | 0.9154 (3) | 0.0445 (14) | |
C4 | 0.1174 (2) | 0.2097 (10) | 0.8381 (3) | 0.0574 (17) | |
H4 | 0.1386 | 0.1161 | 0.8138 | 0.069* | |
C5 | 0.0846 (2) | 0.3602 (11) | 0.7965 (4) | 0.0572 (16) | |
H5 | 0.0846 | 0.3664 | 0.7439 | 0.069* | |
C6 | 0.1538 (2) | 0.0365 (10) | 0.9658 (3) | 0.0482 (14) | |
H6A | 0.1549 | 0.0795 | 1.0189 | 0.058* | |
H6B | 0.1378 | −0.1092 | 0.9596 | 0.058* | |
C7 | 0.2517 (2) | 0.1563 (9) | 0.9751 (3) | 0.0425 (13) | |
C8 | 0.2271 (2) | −0.1350 (10) | 0.9037 (3) | 0.0467 (14) | |
C9 | 0.2813 (2) | −0.0919 (10) | 0.9059 (3) | 0.0463 (14) | |
C10 | 0.3128 (3) | −0.2277 (10) | 0.8663 (3) | 0.0570 (16) | |
H10 | 0.3490 | −0.2005 | 0.8669 | 0.068* | |
C11 | 0.2877 (3) | −0.4028 (11) | 0.8267 (3) | 0.0638 (18) | |
H11 | 0.3076 | −0.4979 | 0.8008 | 0.077* | |
C12 | 0.2336 (3) | −0.4418 (11) | 0.8242 (4) | 0.0695 (19) | |
H12 | 0.2182 | −0.5613 | 0.7961 | 0.083* | |
C13 | 0.2021 (3) | −0.3098 (10) | 0.8619 (4) | 0.0611 (17) | |
H13 | 0.1657 | −0.3360 | 0.8595 | 0.073* | |
Hg1 | 0.0000 | 0.77000 (6) | 0.7500 | 0.05394 (13) | |
I1 | −0.05707 (3) | 0.90708 (11) | 0.85377 (3) | 0.1074 (3) | |
N1 | 0.05302 (18) | 0.4963 (9) | 0.8265 (3) | 0.0548 (13) | |
N2 | 0.20830 (17) | 0.0240 (8) | 0.9488 (3) | 0.0437 (11) | |
N3 | 0.29606 (17) | 0.0913 (8) | 0.9509 (3) | 0.0473 (12) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.059 (4) | 0.094 (5) | 0.060 (4) | 0.032 (4) | 0.014 (3) | 0.007 (4) |
C2 | 0.059 (4) | 0.101 (6) | 0.054 (4) | 0.031 (4) | 0.020 (3) | 0.012 (4) |
C3 | 0.036 (3) | 0.051 (4) | 0.047 (3) | −0.001 (3) | 0.006 (3) | −0.001 (3) |
C4 | 0.055 (4) | 0.060 (4) | 0.056 (4) | 0.016 (3) | 0.006 (3) | −0.011 (3) |
C5 | 0.061 (4) | 0.063 (4) | 0.047 (4) | 0.008 (3) | 0.003 (3) | −0.007 (3) |
C6 | 0.042 (3) | 0.050 (4) | 0.052 (3) | −0.004 (3) | 0.007 (3) | 0.002 (3) |
C7 | 0.044 (3) | 0.043 (3) | 0.040 (3) | 0.006 (3) | 0.001 (3) | 0.004 (2) |
C8 | 0.053 (4) | 0.041 (3) | 0.044 (3) | 0.009 (3) | −0.001 (3) | 0.002 (3) |
C9 | 0.051 (4) | 0.048 (4) | 0.039 (3) | 0.011 (3) | 0.001 (3) | 0.004 (3) |
C10 | 0.058 (4) | 0.058 (4) | 0.056 (4) | 0.018 (3) | 0.011 (3) | 0.006 (3) |
C11 | 0.091 (5) | 0.054 (4) | 0.048 (4) | 0.017 (4) | 0.017 (4) | −0.003 (3) |
C12 | 0.089 (6) | 0.055 (4) | 0.065 (4) | 0.002 (4) | 0.011 (4) | −0.010 (4) |
C13 | 0.065 (4) | 0.049 (4) | 0.067 (4) | 0.001 (3) | 0.003 (4) | −0.003 (3) |
Hg1 | 0.0463 (2) | 0.0654 (3) | 0.0506 (2) | 0.000 | 0.00860 (14) | 0.000 |
I1 | 0.1231 (5) | 0.1306 (6) | 0.0804 (4) | 0.0764 (4) | 0.0547 (3) | 0.0385 (4) |
N1 | 0.042 (3) | 0.072 (4) | 0.048 (3) | 0.009 (3) | 0.000 (2) | −0.001 (3) |
N2 | 0.036 (3) | 0.047 (3) | 0.048 (3) | 0.002 (2) | 0.005 (2) | −0.004 (2) |
N3 | 0.038 (3) | 0.049 (3) | 0.054 (3) | 0.008 (2) | 0.004 (2) | 0.002 (2) |
C1—N1 | 1.317 (7) | C8—N2 | 1.380 (7) |
C1—C2 | 1.373 (8) | C8—C13 | 1.389 (8) |
C1—H1 | 0.9300 | C8—C9 | 1.392 (8) |
C2—C3 | 1.372 (8) | C9—N3 | 1.384 (7) |
C2—H2 | 0.9300 | C9—C10 | 1.404 (8) |
C3—C4 | 1.365 (8) | C10—C11 | 1.374 (9) |
C3—C6 | 1.523 (7) | C10—H10 | 0.9300 |
C4—C5 | 1.371 (8) | C11—C12 | 1.385 (9) |
C4—H4 | 0.9300 | C11—H11 | 0.9300 |
C5—N1 | 1.315 (7) | C12—C13 | 1.370 (8) |
C5—H5 | 0.9300 | C12—H12 | 0.9300 |
C6—N2 | 1.459 (6) | C13—H13 | 0.9300 |
C6—H6A | 0.9700 | Hg1—N1ii | 2.416 (5) |
C6—H6B | 0.9700 | Hg1—N1 | 2.416 (5) |
C7—N3 | 1.321 (7) | Hg1—I1ii | 2.6349 (8) |
C7—N2 | 1.384 (7) | Hg1—I1 | 2.6349 (8) |
C7—C7i | 1.447 (11) | ||
N1—C1—C2 | 123.6 (6) | N3—C9—C10 | 129.2 (6) |
N1—C1—H1 | 118.2 | C8—C9—C10 | 120.5 (6) |
C2—C1—H1 | 118.2 | C11—C10—C9 | 116.9 (6) |
C3—C2—C1 | 119.2 (6) | C11—C10—H10 | 121.6 |
C3—C2—H2 | 120.4 | C9—C10—H10 | 121.6 |
C1—C2—H2 | 120.4 | C10—C11—C12 | 121.9 (6) |
C4—C3—C2 | 117.3 (5) | C10—C11—H11 | 119.1 |
C4—C3—C6 | 122.7 (5) | C12—C11—H11 | 119.1 |
C2—C3—C6 | 120.0 (5) | C13—C12—C11 | 122.1 (6) |
C3—C4—C5 | 119.3 (6) | C13—C12—H12 | 119.0 |
C3—C4—H4 | 120.3 | C11—C12—H12 | 119.0 |
C5—C4—H4 | 120.3 | C12—C13—C8 | 116.8 (6) |
N1—C5—C4 | 123.8 (6) | C12—C13—H13 | 121.6 |
N1—C5—H5 | 118.1 | C8—C13—H13 | 121.6 |
C4—C5—H5 | 118.1 | N1ii—Hg1—N1 | 93.4 (2) |
N2—C6—C3 | 113.8 (5) | N1ii—Hg1—I1ii | 98.24 (12) |
N2—C6—H6A | 108.8 | N1—Hg1—I1ii | 106.80 (12) |
C3—C6—H6A | 108.8 | N1ii—Hg1—I1 | 106.80 (12) |
N2—C6—H6B | 108.8 | N1—Hg1—I1 | 98.24 (12) |
C3—C6—H6B | 108.8 | I1ii—Hg1—I1 | 143.27 (4) |
H6A—C6—H6B | 107.7 | C5—N1—C1 | 116.7 (5) |
N3—C7—N2 | 113.0 (5) | C5—N1—Hg1 | 121.6 (4) |
N3—C7—C7i | 124.2 (7) | C1—N1—Hg1 | 121.5 (4) |
N2—C7—C7i | 122.8 (6) | C8—N2—C7 | 105.8 (4) |
N2—C8—C13 | 132.1 (6) | C8—N2—C6 | 125.1 (5) |
N2—C8—C9 | 106.1 (5) | C7—N2—C6 | 129.1 (5) |
C13—C8—C9 | 121.8 (6) | C7—N3—C9 | 104.8 (5) |
N3—C9—C8 | 110.3 (5) | ||
N1—C1—C2—C3 | −1.6 (12) | C2—C1—N1—Hg1 | −175.5 (6) |
C1—C2—C3—C4 | 1.8 (10) | N1ii—Hg1—N1—C5 | 64.5 (5) |
C1—C2—C3—C6 | −178.9 (6) | I1ii—Hg1—N1—C5 | −35.2 (5) |
C2—C3—C4—C5 | −0.8 (10) | I1—Hg1—N1—C5 | 172.0 (5) |
C6—C3—C4—C5 | −180.0 (6) | N1ii—Hg1—N1—C1 | −120.2 (6) |
C3—C4—C5—N1 | −0.7 (10) | I1ii—Hg1—N1—C1 | 140.2 (5) |
C4—C3—C6—N2 | 45.1 (8) | I1—Hg1—N1—C1 | −12.6 (5) |
C2—C3—C6—N2 | −134.1 (6) | C13—C8—N2—C7 | −179.3 (6) |
N2—C8—C9—N3 | −0.5 (6) | C9—C8—N2—C7 | 0.7 (6) |
C13—C8—C9—N3 | 179.5 (5) | C13—C8—N2—C6 | 3.0 (9) |
N2—C8—C9—C10 | 179.0 (5) | C9—C8—N2—C6 | −177.1 (5) |
C13—C8—C9—C10 | −1.0 (9) | N3—C7—N2—C8 | −0.7 (6) |
N3—C9—C10—C11 | 178.9 (6) | C7i—C7—N2—C8 | −179.8 (6) |
C8—C9—C10—C11 | −0.5 (8) | N3—C7—N2—C6 | 176.9 (5) |
C9—C10—C11—C12 | 1.4 (9) | C7i—C7—N2—C6 | −2.2 (10) |
C10—C11—C12—C13 | −0.8 (10) | C3—C6—N2—C8 | −97.9 (6) |
C11—C12—C13—C8 | −0.7 (10) | C3—C6—N2—C7 | 84.8 (7) |
N2—C8—C13—C12 | −178.4 (6) | N2—C7—N3—C9 | 0.5 (6) |
C9—C8—C13—C12 | 1.6 (9) | C7i—C7—N3—C9 | 179.5 (6) |
C4—C5—N1—C1 | 1.0 (10) | C8—C9—N3—C7 | 0.0 (6) |
C4—C5—N1—Hg1 | 176.6 (5) | C10—C9—N3—C7 | −179.4 (5) |
C2—C1—N1—C5 | 0.1 (11) |
Symmetry codes: (i) −x+1/2, −y+1/2, −z+2; (ii) −x, y, −z+3/2. |
D—H···A | H···A | D···A | D—H···A |
C12—H12···Cl1v | 2.86 | 3.555 (6) | 132 |
C2—H2···Br1iii | 3.08 | 3.875 (6) | 145 |
C2—H2···I1iii | 3.19 | 3.998 (7) | 147 |
Symmetry codes: (iii) -x, -y+1, -z+2; (v) x, -y, z+1/2. |