Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680603296X/ez2020sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680603296X/ez2020Isup2.hkl |
CCDC reference: 620961
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.006 Å
- R factor = 0.026
- wR factor = 0.053
- Data-to-parameter ratio = 25.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Pd1
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 28.30 From the CIF: _reflns_number_total 5993 Count of symmetry unique reflns 3142 Completeness (_total/calc) 190.74% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2851 Fraction of Friedel pairs measured 0.907 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2005); cell refinement: SMART; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 2000).
(C8H15N2)2[PdBr4] | Dx = 1.940 Mg m−3 |
Mr = 704.46 | Melting point = 396.5–397.3 K |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 7186 reflections |
a = 21.6041 (8) Å | θ = 2.4–23.1° |
b = 9.1708 (3) Å | µ = 7.40 mm−1 |
c = 12.1753 (4) Å | T = 294 K |
V = 2412.25 (14) Å3 | Needle, purple–red |
Z = 4 | 0.20 × 0.20 × 0.18 mm |
F(000) = 1360 |
Bruker SMART APEX CCD area-detector diffractometer | 5993 independent reflections |
Radiation source: fine-focus sealed tube | 4817 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
φ and ω scans | θmax = 28.3°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2005) | h = −28→28 |
Tmin = 0.230, Tmax = 0.264 | k = −12→12 |
24651 measured reflections | l = −16→16 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.026 | H-atom parameters constrained |
wR(F2) = 0.053 | w = 1/[σ2(Fo2) + (0.0383P)2 + 1.1806P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
5993 reflections | Δρmax = 0.34 e Å−3 |
231 parameters | Δρmin = −0.38 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 2851 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.02 (2) |
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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) - 6.3043 (0.0241) x - 7.9188 (0.0097) y + 5.0089 (0.0256) z = 1.7249 (0.0222) * -0.0079 (0.0037) C1 * -0.0005 (0.0032) C2 * 0.0059 (0.0032) C3 * -0.0092 (0.0036) N1 * -0.0164 (0.0032) N2 * 0.0147 (0.0026) C4 * 0.0133 (0.0029) C8 Rms deviation of fitted atoms = 0.0110 5.8979 (0.0328) x + 7.3449 (0.0119) y - 6.4888 (0.0216) z = 0.2792 (0.0094) Angle to previous plane (with approximate e.s.d.) = 7.91 (0.27) * -0.0061 (0.0027) C9 * -0.0067 (0.0034) C10 * 0.0071 (0.0035) C11 * 0.0114 (0.0024) C16 * -0.0118 (0.0034) N3 * 0.0060 (0.0028) N4 Rms deviation of fitted atoms = 0.0085 - 6.1540 (0.0027) x + 0.5946 (0.0012) y + 11.6442 (0.0006) z = 0.3094 (0.0009) Angle to previous plane (with approximate e.s.d.) = 57.62 (0.12) * 0.0285 (0.0002) Br1 * -0.0285 (0.0002) Br2 * 0.0288 (0.0002) Br3 * -0.0284 (0.0002) Br4 * -0.0005 (0.0003) Pd1 Rms deviation of fitted atoms = 0.0255 |
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 | ||
N1 | 0.16251 (17) | 0.1678 (4) | 0.8124 (3) | 0.0574 (9) | |
N2 | 0.06762 (16) | 0.2224 (4) | 0.7778 (3) | 0.0522 (8) | |
C1 | 0.1119 (2) | 0.2326 (5) | 0.8513 (4) | 0.0560 (11) | |
H1 | 0.1084 | 0.2777 | 0.9194 | 0.067* | |
C2 | 0.1490 (2) | 0.1127 (5) | 0.7100 (4) | 0.0691 (12) | |
H2 | 0.1760 | 0.0621 | 0.6642 | 0.083* | |
C3 | 0.0895 (2) | 0.1458 (5) | 0.6886 (4) | 0.0663 (12) | |
H3 | 0.0674 | 0.1215 | 0.6257 | 0.080* | |
C4 | 0.0041 (2) | 0.2773 (5) | 0.7908 (4) | 0.0649 (12) | |
H4A | −0.0160 | 0.2789 | 0.7197 | 0.078* | |
H4B | 0.0056 | 0.3765 | 0.8182 | 0.078* | |
C5 | −0.0334 (2) | 0.1855 (5) | 0.8683 (4) | 0.0702 (13) | |
H5A | −0.0338 | 0.0863 | 0.8408 | 0.084* | |
H5B | −0.0126 | 0.1843 | 0.9389 | 0.084* | |
C6 | −0.0979 (2) | 0.2324 (6) | 0.8857 (4) | 0.0777 (14) | |
H6A | −0.1197 | 0.2280 | 0.8162 | 0.093* | |
H6B | −0.0980 | 0.3331 | 0.9099 | 0.093* | |
C7 | −0.1316 (2) | 0.1423 (6) | 0.9676 (5) | 0.0868 (16) | |
H7A | −0.1283 | 0.0412 | 0.9479 | 0.130* | |
H7B | −0.1744 | 0.1704 | 0.9687 | 0.130* | |
H7C | −0.1138 | 0.1572 | 1.0390 | 0.130* | |
C8 | 0.2217 (2) | 0.1541 (6) | 0.8697 (5) | 0.0797 (15) | |
H8A | 0.2276 | 0.2367 | 0.9171 | 0.120* | |
H8B | 0.2547 | 0.1502 | 0.8170 | 0.120* | |
H8C | 0.2218 | 0.0664 | 0.9127 | 0.120* | |
N3 | 0.08872 (14) | 0.2164 (4) | 0.2843 (3) | 0.0507 (8) | |
N4 | 0.18466 (15) | 0.1722 (4) | 0.3188 (3) | 0.0506 (8) | |
C9 | 0.13894 (17) | 0.1469 (4) | 0.2505 (3) | 0.0466 (9) | |
H9 | 0.1414 | 0.0891 | 0.1879 | 0.056* | |
C10 | 0.1038 (2) | 0.2886 (5) | 0.3789 (4) | 0.0698 (13) | |
H10 | 0.0773 | 0.3461 | 0.4208 | 0.084* | |
C11 | 0.1629 (2) | 0.2619 (5) | 0.4003 (4) | 0.0650 (12) | |
H11 | 0.1854 | 0.2974 | 0.4596 | 0.078* | |
C12 | 0.24776 (17) | 0.1125 (5) | 0.3113 (4) | 0.0541 (10) | |
H12A | 0.2472 | 0.0253 | 0.2662 | 0.065* | |
H12B | 0.2618 | 0.0852 | 0.3841 | 0.065* | |
C13 | 0.29225 (18) | 0.2202 (5) | 0.2628 (4) | 0.0636 (11) | |
H13A | 0.2944 | 0.3053 | 0.3099 | 0.076* | |
H13B | 0.2769 | 0.2515 | 0.1917 | 0.076* | |
C14 | 0.3577 (2) | 0.1565 (5) | 0.2489 (4) | 0.0703 (13) | |
H14A | 0.3858 | 0.2347 | 0.2293 | 0.084* | |
H14B | 0.3712 | 0.1167 | 0.3187 | 0.084* | |
C15 | 0.3616 (2) | 0.0401 (5) | 0.1636 (5) | 0.0801 (15) | |
H15A | 0.3404 | 0.0715 | 0.0984 | 0.120* | |
H15B | 0.3426 | −0.0474 | 0.1909 | 0.120* | |
H15C | 0.4042 | 0.0212 | 0.1467 | 0.120* | |
C16 | 0.02809 (18) | 0.2195 (5) | 0.2292 (5) | 0.0747 (14) | |
H16A | 0.0246 | 0.1369 | 0.1811 | 0.112* | |
H16B | 0.0244 | 0.3077 | 0.1872 | 0.112* | |
H16C | −0.0042 | 0.2159 | 0.2833 | 0.112* | |
Pd1 | 0.121908 (11) | 0.68316 (3) | 0.05607 (3) | 0.03914 (6) | |
Br1 | 0.031465 (18) | 0.53296 (4) | 0.01843 (3) | 0.06008 (11) | |
Br2 | 0.18157 (2) | 0.46384 (4) | 0.09640 (4) | 0.06423 (12) | |
Br3 | 0.211532 (17) | 0.83283 (5) | 0.09831 (4) | 0.06357 (12) | |
Br4 | 0.06354 (2) | 0.90334 (4) | 0.01158 (4) | 0.06590 (12) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.056 (2) | 0.055 (2) | 0.061 (2) | −0.0056 (18) | −0.0035 (18) | 0.0034 (17) |
N2 | 0.061 (2) | 0.051 (2) | 0.045 (2) | −0.0029 (16) | −0.0004 (17) | 0.0033 (15) |
C1 | 0.062 (3) | 0.056 (3) | 0.050 (3) | 0.000 (2) | −0.002 (2) | 0.000 (2) |
C2 | 0.077 (3) | 0.064 (3) | 0.066 (3) | −0.005 (2) | 0.008 (2) | −0.011 (2) |
C3 | 0.072 (3) | 0.072 (3) | 0.055 (3) | −0.012 (2) | 0.003 (2) | −0.012 (2) |
C4 | 0.076 (3) | 0.072 (3) | 0.047 (3) | 0.011 (2) | −0.006 (2) | 0.002 (2) |
C5 | 0.071 (3) | 0.058 (3) | 0.081 (4) | 0.003 (2) | 0.000 (2) | 0.006 (2) |
C6 | 0.070 (3) | 0.096 (4) | 0.067 (3) | 0.021 (3) | −0.006 (3) | 0.005 (3) |
C7 | 0.080 (4) | 0.087 (4) | 0.093 (4) | −0.009 (3) | 0.013 (3) | −0.012 (3) |
C8 | 0.076 (3) | 0.084 (4) | 0.079 (4) | 0.001 (3) | −0.011 (3) | 0.002 (3) |
N3 | 0.043 (2) | 0.054 (2) | 0.056 (2) | 0.0040 (15) | 0.0040 (15) | 0.0066 (16) |
N4 | 0.0432 (19) | 0.049 (2) | 0.060 (2) | 0.0025 (15) | −0.0003 (16) | −0.0052 (16) |
C9 | 0.044 (2) | 0.046 (2) | 0.050 (2) | 0.0018 (17) | 0.0030 (18) | −0.0001 (18) |
C10 | 0.064 (3) | 0.071 (3) | 0.075 (3) | 0.010 (2) | 0.014 (2) | −0.019 (3) |
C11 | 0.063 (3) | 0.071 (3) | 0.060 (3) | −0.001 (2) | 0.000 (2) | −0.024 (2) |
C12 | 0.047 (2) | 0.052 (2) | 0.064 (3) | 0.0017 (18) | −0.0033 (19) | 0.000 (2) |
C13 | 0.057 (2) | 0.063 (3) | 0.071 (3) | 0.004 (2) | 0.011 (2) | 0.001 (2) |
C14 | 0.051 (2) | 0.094 (4) | 0.066 (3) | −0.003 (2) | −0.005 (2) | 0.005 (3) |
C15 | 0.058 (3) | 0.078 (3) | 0.104 (4) | 0.014 (2) | 0.017 (3) | 0.007 (3) |
C16 | 0.050 (3) | 0.084 (4) | 0.091 (4) | 0.012 (2) | −0.008 (2) | 0.012 (3) |
Pd1 | 0.03786 (12) | 0.04298 (12) | 0.03656 (11) | 0.00460 (10) | 0.00091 (11) | 0.00095 (11) |
Br1 | 0.0469 (2) | 0.0615 (2) | 0.0719 (3) | −0.00494 (17) | −0.00524 (19) | −0.0040 (2) |
Br2 | 0.0604 (2) | 0.0551 (2) | 0.0772 (3) | 0.01601 (18) | −0.0112 (2) | 0.0085 (2) |
Br3 | 0.0480 (2) | 0.0666 (3) | 0.0761 (3) | −0.00748 (18) | 0.0026 (2) | −0.0152 (2) |
Br4 | 0.0674 (3) | 0.0518 (2) | 0.0785 (3) | 0.0175 (2) | −0.0079 (2) | 0.0069 (2) |
N1—C1 | 1.332 (6) | N3—C16 | 1.472 (5) |
N1—C2 | 1.376 (6) | N4—C9 | 1.312 (5) |
N1—C8 | 1.463 (6) | N4—C11 | 1.372 (5) |
N2—C1 | 1.313 (5) | N4—C12 | 1.472 (5) |
N2—C3 | 1.376 (6) | C9—H9 | 0.9300 |
N2—C4 | 1.470 (5) | C10—C11 | 1.326 (6) |
C1—H1 | 0.9300 | C10—H10 | 0.9300 |
C2—C3 | 1.348 (7) | C11—H11 | 0.9300 |
C2—H2 | 0.9300 | C12—C13 | 1.499 (6) |
C3—H3 | 0.9300 | C12—H12A | 0.9700 |
C4—C5 | 1.501 (6) | C12—H12B | 0.9700 |
C4—H4A | 0.9700 | C13—C14 | 1.538 (6) |
C4—H4B | 0.9700 | C13—H13A | 0.9700 |
C5—C6 | 1.473 (6) | C13—H13B | 0.9700 |
C5—H5A | 0.9700 | C14—C15 | 1.491 (7) |
C5—H5B | 0.9700 | C14—H14A | 0.9700 |
C6—C7 | 1.486 (7) | C14—H14B | 0.9700 |
C6—H6A | 0.9700 | C15—H15A | 0.9600 |
C6—H6B | 0.9700 | C15—H15B | 0.9600 |
C7—H7A | 0.9600 | C15—H15C | 0.9600 |
C7—H7B | 0.9600 | C16—H16A | 0.9600 |
C7—H7C | 0.9600 | C16—H16B | 0.9600 |
C8—H8A | 0.9600 | C16—H16C | 0.9600 |
C8—H8B | 0.9600 | Pd1—Br3 | 2.4285 (5) |
C8—H8C | 0.9600 | Pd1—Br1 | 2.4342 (4) |
N3—C9 | 1.324 (5) | Pd1—Br2 | 2.4388 (4) |
N3—C10 | 1.368 (6) | Pd1—Br4 | 2.4415 (5) |
C1—N1—C2 | 108.2 (4) | C9—N4—C11 | 107.8 (4) |
C1—N1—C8 | 126.0 (4) | C9—N4—C12 | 126.3 (4) |
C2—N1—C8 | 125.8 (4) | C11—N4—C12 | 125.8 (4) |
C1—N2—C3 | 108.9 (4) | N4—C9—N3 | 109.5 (4) |
C1—N2—C4 | 125.5 (4) | N4—C9—H9 | 125.2 |
C3—N2—C4 | 125.5 (4) | N3—C9—H9 | 125.2 |
N2—C1—N1 | 108.9 (4) | C11—C10—N3 | 107.8 (4) |
N2—C1—H1 | 125.5 | C11—C10—H10 | 126.1 |
N1—C1—H1 | 125.5 | N3—C10—H10 | 126.1 |
C3—C2—N1 | 107.1 (4) | C10—C11—N4 | 107.4 (4) |
C3—C2—H2 | 126.5 | C10—C11—H11 | 126.3 |
N1—C2—H2 | 126.5 | N4—C11—H11 | 126.3 |
C2—C3—N2 | 106.9 (4) | N4—C12—C13 | 111.9 (3) |
C2—C3—H3 | 126.6 | N4—C12—H12A | 109.2 |
N2—C3—H3 | 126.6 | C13—C12—H12A | 109.2 |
N2—C4—C5 | 112.3 (4) | N4—C12—H12B | 109.2 |
N2—C4—H4A | 109.1 | C13—C12—H12B | 109.2 |
C5—C4—H4A | 109.1 | H12A—C12—H12B | 107.9 |
N2—C4—H4B | 109.1 | C12—C13—C14 | 112.5 (4) |
C5—C4—H4B | 109.1 | C12—C13—H13A | 109.1 |
H4A—C4—H4B | 107.9 | C14—C13—H13A | 109.1 |
C6—C5—C4 | 115.9 (4) | C12—C13—H13B | 109.1 |
C6—C5—H5A | 108.3 | C14—C13—H13B | 109.1 |
C4—C5—H5A | 108.3 | H13A—C13—H13B | 107.8 |
C6—C5—H5B | 108.3 | C15—C14—C13 | 113.6 (4) |
C4—C5—H5B | 108.3 | C15—C14—H14A | 108.8 |
H5A—C5—H5B | 107.4 | C13—C14—H14A | 108.8 |
C5—C6—C7 | 113.4 (4) | C15—C14—H14B | 108.8 |
C5—C6—H6A | 108.9 | C13—C14—H14B | 108.8 |
C7—C6—H6A | 108.9 | H14A—C14—H14B | 107.7 |
C5—C6—H6B | 108.9 | C14—C15—H15A | 109.5 |
C7—C6—H6B | 108.9 | C14—C15—H15B | 109.5 |
H6A—C6—H6B | 107.7 | H15A—C15—H15B | 109.5 |
C6—C7—H7A | 109.5 | C14—C15—H15C | 109.5 |
C6—C7—H7B | 109.5 | H15A—C15—H15C | 109.5 |
H7A—C7—H7B | 109.5 | H15B—C15—H15C | 109.5 |
C6—C7—H7C | 109.5 | N3—C16—H16A | 109.5 |
H7A—C7—H7C | 109.5 | N3—C16—H16B | 109.5 |
H7B—C7—H7C | 109.5 | H16A—C16—H16B | 109.5 |
N1—C8—H8A | 109.5 | N3—C16—H16C | 109.5 |
N1—C8—H8B | 109.5 | H16A—C16—H16C | 109.5 |
H8A—C8—H8B | 109.5 | H16B—C16—H16C | 109.5 |
N1—C8—H8C | 109.5 | Br3—Pd1—Br1 | 178.62 (2) |
H8A—C8—H8C | 109.5 | Br3—Pd1—Br2 | 90.121 (17) |
H8B—C8—H8C | 109.5 | Br1—Pd1—Br2 | 89.738 (16) |
C9—N3—C10 | 107.5 (3) | Br3—Pd1—Br4 | 89.505 (17) |
C9—N3—C16 | 126.6 (4) | Br1—Pd1—Br4 | 90.668 (16) |
C10—N3—C16 | 125.9 (4) | Br2—Pd1—Br4 | 178.63 (2) |
C3—N2—C1—N1 | 1.3 (5) | C11—N4—C9—N3 | 0.0 (5) |
C4—N2—C1—N1 | 178.4 (4) | C12—N4—C9—N3 | 178.7 (4) |
C2—N1—C1—N2 | −0.8 (5) | C10—N3—C9—N4 | −0.2 (5) |
C8—N1—C1—N2 | −179.3 (4) | C16—N3—C9—N4 | 178.2 (4) |
C1—N1—C2—C3 | 0.0 (5) | C9—N3—C10—C11 | 0.2 (5) |
C8—N1—C2—C3 | 178.5 (4) | C16—N3—C10—C11 | −178.2 (4) |
N1—C2—C3—N2 | 0.8 (5) | N3—C10—C11—N4 | −0.2 (6) |
C1—N2—C3—C2 | −1.3 (5) | C9—N4—C11—C10 | 0.1 (5) |
C4—N2—C3—C2 | −178.4 (4) | C12—N4—C11—C10 | −178.6 (4) |
C1—N2—C4—C5 | −73.3 (6) | C9—N4—C12—C13 | 99.9 (5) |
C3—N2—C4—C5 | 103.4 (5) | C11—N4—C12—C13 | −81.7 (5) |
N2—C4—C5—C6 | −179.6 (4) | N4—C12—C13—C14 | −177.0 (4) |
C4—C5—C6—C7 | −176.9 (5) | C12—C13—C14—C15 | 68.2 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4B···Br1i | 0.97 | 2.88 | 3.678 (5) | 140 |
C10—H10···Br1ii | 0.93 | 2.86 | 3.755 (5) | 163 |
C11—H11···Br3iii | 0.93 | 2.81 | 3.687 (5) | 157 |
C12—H12A···Br3iv | 0.97 | 2.81 | 3.730 (5) | 159 |
C16—H16B···Br1 | 0.96 | 2.92 | 3.854 (5) | 165 |
Symmetry codes: (i) x, y, z+1; (ii) −x, −y+1, z+1/2; (iii) −x+1/2, y−1/2, z+1/2; (iv) x, y−1, z. |