Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520621004753/xk5082sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520621004753/xk5082NNBiCl_1_295Ksup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520621004753/xk5082NNBiCl_1_100Ksup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520621004753/xk5082NNBiCl_2_295Ksup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520621004753/xk5082TmgBiCl_3_295Ksup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520621004753/xk5082TmgBiCl_4_295Ksup6.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2052520621004753/xk5082sup7.pdf |
CCDC references: 2067265; 2067266; 2067267; 2067268; 2067269
For all structures, data collection: CrysAlis CCD 1.171.29.10 (Oxford Diffraction, 2006); cell refinement: CrysAlis PRO 1.171.40.56a (Rigaku Oxford Diffraction, 2019); data reduction: CrysAlis PRO 1.171.40.56a (Rigaku Oxford Diffraction, 2019); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2014); molecular graphics: Mercury (Macrae at al., 2020); software used to prepare material for publication: SHELXL2014/7 (Sheldrick, 2014).
(C4H14N2)3[BiCl6]2 | F(000) = 2104 |
Mr = 1113.88 | Dx = 2.144 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 27.8842 (4) Å | Cell parameters from 8308 reflections |
b = 10.19431 (13) Å | θ = 3.2–29.5° |
c = 12.45639 (17) Å | µ = 11.13 mm−1 |
β = 102.9110 (14)° | T = 295 K |
V = 3451.34 (8) Å3 | Plate, colourless |
Z = 4 | 0.25 × 0.16 × 0.09 mm |
Xcalibur diffractometer | 3130 reflections with I > 2σ(I) |
ω–scan | Rint = 0.017 |
Absorption correction: multi-scan CrysAlisPro 1.171.40.56a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | θmax = 26.0°, θmin = 3.0° |
Tmin = 0.30, Tmax = 1.00 | h = −34→34 |
11329 measured reflections | k = −9→12 |
3386 independent reflections | l = −15→15 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.016 | H-atom parameters constrained |
wR(F2) = 0.037 | w = 1/[σ2(Fo2) + (0.0163P)2 + 4.6776P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.003 |
3386 reflections | Δρmax = 0.63 e Å−3 |
189 parameters | Δρmin = −0.45 e Å−3 |
18 restraints | Extinction correction: SHELXL-2014/7 (Sheldrick 2014, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00068 (2) |
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) | |
Bi1 | 0.12880 (2) | 0.19413 (2) | 0.59479 (2) | 0.03268 (5) | |
Cl1 | 0.14239 (4) | 0.07948 (9) | 0.79109 (7) | 0.0631 (3) | |
Cl2 | 0.12098 (3) | 0.31871 (8) | 0.39393 (7) | 0.04733 (19) | |
Cl3 | 0.18255 (3) | 0.40206 (7) | 0.68834 (6) | 0.04779 (19) | |
Cl4 | 0.07140 (3) | −0.00882 (8) | 0.50912 (7) | 0.0525 (2) | |
Cl5 | 0.21238 (3) | 0.08005 (9) | 0.56471 (7) | 0.0559 (2) | |
Cl6 | 0.04708 (4) | 0.31178 (11) | 0.63193 (11) | 0.0798 (3) | |
N21 | 0.20715 (11) | 0.8141 (3) | 0.8035 (2) | 0.0542 (7) | |
H211 | 0.2383 | 0.8247 | 0.8392 | 0.081* | |
H212 | 0.1922 | 0.7596 | 0.8412 | 0.081* | |
H213 | 0.1919 | 0.8914 | 0.7966 | 0.081* | |
C21 | 0.20558 (13) | 0.7592 (4) | 0.6935 (3) | 0.0528 (8) | |
H214 | 0.2235 | 0.6769 | 0.7012 | 0.063* | |
H215 | 0.2218 | 0.8191 | 0.6526 | 0.063* | |
C22 | 0.15403 (12) | 0.7362 (3) | 0.6307 (3) | 0.0454 (7) | |
H223 | 0.1417 | 0.6578 | 0.6595 | 0.054* | |
H224 | 0.1339 | 0.8091 | 0.6446 | 0.054* | |
N221 | 0.14721 (17) | 0.7210 (5) | 0.5098 (4) | 0.0482 (12) | 0.660 (8) |
H221 | 0.1472 | 0.8091 | 0.4783 | 0.058* | 0.660 (8) |
N222 | 0.1510 (3) | 0.6437 (10) | 0.5384 (7) | 0.0428 (19) | 0.340 (8) |
H222 | 0.1516 | 0.5557 | 0.5703 | 0.051* | 0.340 (8) |
C23 | 0.09882 (15) | 0.6601 (4) | 0.4610 (3) | 0.0663 (11) | |
H231 | 0.0940 | 0.6583 | 0.3822 | 0.099* | |
H232 | 0.0731 | 0.7106 | 0.4810 | 0.099* | |
H233 | 0.0981 | 0.5722 | 0.4882 | 0.099* | |
C24 | 0.18779 (16) | 0.6442 (4) | 0.4764 (3) | 0.0671 (11) | |
H241 | 0.2183 | 0.6910 | 0.4987 | 0.101* | |
H242 | 0.1802 | 0.6331 | 0.3979 | 0.101* | |
H243 | 0.1907 | 0.5598 | 0.5114 | 0.101* | |
N11 | −0.0090 (4) | −0.0775 (5) | 0.2653 (10) | 0.058 (2) | 0.5 |
H111 | −0.0090 | −0.0789 | 0.3367 | 0.086* | 0.5 |
H112 | 0.0078 | −0.1461 | 0.2490 | 0.086* | 0.5 |
H113 | −0.0398 | −0.0814 | 0.2259 | 0.086* | 0.5 |
C11 | 0.0142 (2) | 0.0444 (6) | 0.2391 (5) | 0.0393 (14) | 0.5 |
H114 | 0.0119 | 0.0498 | 0.1603 | 0.047* | 0.5 |
H115 | 0.0487 | 0.0450 | 0.2760 | 0.047* | 0.5 |
C12 | −0.0117 (2) | 0.1610 (6) | 0.2767 (5) | 0.0408 (14) | 0.5 |
H122 | −0.0456 | 0.1635 | 0.2354 | 0.049* | 0.5 |
H123 | −0.0119 | 0.1507 | 0.3540 | 0.049* | 0.5 |
N12 | 0.01278 (16) | 0.2863 (5) | 0.2610 (6) | 0.0428 (14) | 0.5 |
H121 | 0.0478 | 0.2758 | 0.2950 | 0.051* | 0.5 |
C13 | 0.0084 (3) | 0.3990 (8) | 0.1891 (7) | 0.060 (2) | 0.5 |
H131 | −0.0047 | 0.3720 | 0.1144 | 0.090* | 0.5 |
H132 | 0.0402 | 0.4378 | 0.1947 | 0.090* | 0.5 |
H133 | −0.0133 | 0.4621 | 0.2104 | 0.090* | 0.5 |
C14 | −0.0138 (3) | 0.3143 (8) | 0.3549 (7) | 0.0554 (18) | 0.5 |
H141 | 0.0100 | 0.3358 | 0.4210 | 0.083* | 0.5 |
H142 | −0.0319 | 0.2380 | 0.3676 | 0.083* | 0.5 |
H143 | −0.0361 | 0.3866 | 0.3346 | 0.083* | 0.5 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Bi1 | 0.03254 (7) | 0.03421 (7) | 0.03032 (7) | 0.00249 (4) | 0.00497 (4) | 0.00204 (4) |
Cl1 | 0.1046 (8) | 0.0494 (5) | 0.0396 (4) | 0.0095 (5) | 0.0250 (5) | 0.0098 (4) |
Cl2 | 0.0458 (4) | 0.0540 (5) | 0.0396 (4) | −0.0010 (3) | 0.0040 (3) | 0.0097 (3) |
Cl3 | 0.0573 (5) | 0.0402 (4) | 0.0406 (4) | −0.0056 (3) | −0.0002 (4) | 0.0021 (3) |
Cl4 | 0.0532 (5) | 0.0522 (5) | 0.0479 (4) | −0.0114 (4) | 0.0024 (4) | −0.0035 (4) |
Cl5 | 0.0420 (4) | 0.0650 (5) | 0.0597 (5) | 0.0116 (4) | 0.0093 (4) | −0.0031 (4) |
Cl6 | 0.0629 (6) | 0.0810 (7) | 0.0960 (8) | 0.0308 (5) | 0.0188 (6) | −0.0121 (6) |
N21 | 0.0446 (17) | 0.068 (2) | 0.0472 (17) | 0.0034 (14) | 0.0034 (13) | −0.0123 (14) |
C21 | 0.048 (2) | 0.062 (2) | 0.0460 (19) | −0.0005 (17) | 0.0071 (16) | −0.0123 (17) |
C22 | 0.0490 (19) | 0.0435 (17) | 0.0393 (17) | 0.0097 (15) | 0.0008 (14) | −0.0025 (14) |
N221 | 0.061 (2) | 0.045 (3) | 0.035 (2) | 0.000 (2) | 0.0030 (18) | 0.0036 (18) |
N222 | 0.051 (3) | 0.040 (3) | 0.034 (3) | 0.002 (3) | 0.003 (3) | 0.003 (3) |
C23 | 0.069 (3) | 0.063 (2) | 0.055 (2) | 0.000 (2) | −0.0121 (19) | −0.0109 (19) |
C24 | 0.083 (3) | 0.081 (3) | 0.043 (2) | −0.002 (2) | 0.026 (2) | −0.0013 (19) |
N11 | 0.065 (7) | 0.045 (3) | 0.064 (7) | −0.003 (3) | 0.018 (4) | −0.002 (3) |
C11 | 0.035 (4) | 0.048 (4) | 0.034 (3) | 0.001 (2) | 0.007 (3) | 0.001 (3) |
C12 | 0.033 (3) | 0.052 (4) | 0.038 (4) | 0.006 (3) | 0.009 (2) | 0.003 (3) |
N12 | 0.030 (4) | 0.046 (3) | 0.050 (4) | 0.0008 (19) | 0.004 (4) | −0.008 (3) |
C13 | 0.050 (4) | 0.063 (5) | 0.066 (5) | −0.006 (4) | 0.009 (4) | 0.019 (4) |
C14 | 0.056 (5) | 0.055 (5) | 0.055 (5) | 0.002 (4) | 0.013 (4) | −0.005 (4) |
Bi1—Cl1 | 2.6597 (8) | C23—H233 | 0.9600 |
Bi1—Cl4 | 2.6866 (8) | C24—H241 | 0.9600 |
Bi1—Cl5 | 2.7045 (8) | C24—H242 | 0.9600 |
Bi1—Cl6 | 2.7047 (10) | C24—H243 | 0.9600 |
Bi1—Cl3 | 2.7049 (8) | N11—C11 | 1.471 (7) |
Bi1—Cl2 | 2.7707 (8) | N11—H111 | 0.8900 |
N21—C21 | 1.471 (4) | N11—H112 | 0.8900 |
N21—H211 | 0.8900 | N11—H113 | 0.8900 |
N21—H212 | 0.8900 | C11—C12 | 1.518 (8) |
N21—H213 | 0.8900 | C11—H114 | 0.9700 |
C21—C22 | 1.494 (5) | C11—H115 | 0.9700 |
C21—H214 | 0.9700 | C12—N12 | 1.481 (8) |
C21—H215 | 0.9700 | C12—C14 | 1.850 (9) |
C22—N222 | 1.475 (8) | C12—H122 | 0.9700 |
C22—N221 | 1.483 (5) | C12—H123 | 0.9700 |
C22—H223 | 0.9700 | N12—C13 | 1.445 (9) |
C22—H224 | 0.9700 | N12—C14 | 1.547 (11) |
N221—C23 | 1.486 (6) | N12—H121 | 0.9800 |
N221—C24 | 1.508 (6) | C13—H131 | 0.9600 |
N221—H221 | 0.9800 | C13—H132 | 0.9600 |
N222—C24 | 1.415 (9) | C13—H133 | 0.9600 |
N222—C23 | 1.565 (9) | C14—H141 | 0.9600 |
N222—H222 | 0.9800 | C14—H142 | 0.9600 |
C23—H231 | 0.9600 | C14—H143 | 0.9600 |
C23—H232 | 0.9600 | ||
Cl1—Bi1—Cl4 | 88.66 (3) | H232—C23—H233 | 109.5 |
Cl1—Bi1—Cl5 | 89.33 (3) | N221—C24—H241 | 109.5 |
Cl4—Bi1—Cl5 | 93.97 (3) | N221—C24—H242 | 109.5 |
Cl1—Bi1—Cl6 | 89.43 (4) | H241—C24—H242 | 109.5 |
Cl4—Bi1—Cl6 | 87.68 (3) | N221—C24—H243 | 109.5 |
Cl5—Bi1—Cl6 | 177.91 (3) | H241—C24—H243 | 109.5 |
Cl1—Bi1—Cl3 | 89.82 (3) | H242—C24—H243 | 109.5 |
Cl4—Bi1—Cl3 | 176.53 (3) | C11—N11—H111 | 109.5 |
Cl5—Bi1—Cl3 | 89.14 (3) | C11—N11—H112 | 109.5 |
Cl6—Bi1—Cl3 | 89.18 (3) | H111—N11—H112 | 109.5 |
Cl1—Bi1—Cl2 | 176.27 (3) | C11—N11—H113 | 109.5 |
Cl4—Bi1—Cl2 | 94.28 (2) | H111—N11—H113 | 109.5 |
Cl5—Bi1—Cl2 | 88.19 (3) | H112—N11—H113 | 109.5 |
Cl6—Bi1—Cl2 | 92.97 (3) | N11—C11—C12 | 109.3 (5) |
Cl3—Bi1—Cl2 | 87.37 (2) | N11—C11—H114 | 109.8 |
C21—N21—H211 | 109.5 | C12—C11—H114 | 109.8 |
C21—N21—H212 | 109.5 | N11—C11—H115 | 109.8 |
H211—N21—H212 | 109.5 | C12—C11—H115 | 109.8 |
C21—N21—H213 | 109.5 | H114—C11—H115 | 108.3 |
H211—N21—H213 | 109.5 | N12—C12—C11 | 111.6 (5) |
H212—N21—H213 | 109.5 | N12—C12—C14 | 54.0 (4) |
N21—C21—C22 | 111.9 (3) | C11—C12—C14 | 153.9 (5) |
N21—C21—H214 | 109.2 | N12—C12—H122 | 109.3 |
C22—C21—H214 | 109.2 | C11—C12—H122 | 109.3 |
N21—C21—H215 | 109.2 | C14—C12—H122 | 96.6 |
C22—C21—H215 | 109.2 | N12—C12—H123 | 109.3 |
H214—C21—H215 | 107.9 | C11—C12—H123 | 109.3 |
N222—C22—C21 | 112.9 (4) | C14—C12—H123 | 63.9 |
N221—C22—C21 | 116.0 (3) | H122—C12—H123 | 108.0 |
N221—C22—H223 | 108.3 | C13—N12—C12 | 142.2 (6) |
C21—C22—H223 | 108.3 | C13—N12—C14 | 109.5 (6) |
N221—C22—H224 | 108.3 | C12—N12—C14 | 75.3 (5) |
C21—C22—H224 | 108.3 | C13—N12—H121 | 107.0 |
H223—C22—H224 | 107.4 | C12—N12—H121 | 107.0 |
C22—N221—C23 | 111.0 (4) | C14—N12—H121 | 107.0 |
C22—N221—C24 | 113.6 (4) | N12—C13—H131 | 109.5 |
C23—N221—C24 | 109.8 (4) | N12—C13—H132 | 109.5 |
C22—N221—H221 | 107.4 | H131—C13—H132 | 109.5 |
C23—N221—H221 | 107.4 | N12—C13—H133 | 109.5 |
C24—N221—H221 | 107.4 | H131—C13—H133 | 109.5 |
C24—N222—C22 | 120.0 (7) | H132—C13—H133 | 109.5 |
C24—N222—C23 | 110.6 (6) | N12—C14—C12 | 50.8 (3) |
C22—N222—C23 | 107.2 (6) | N12—C14—H141 | 109.5 |
C24—N222—H222 | 106.0 | C12—C14—H141 | 123.1 |
C22—N222—H222 | 106.0 | N12—C14—H142 | 109.5 |
C23—N222—H222 | 106.0 | C12—C14—H142 | 58.8 |
N221—C23—H231 | 109.5 | H141—C14—H142 | 109.5 |
N221—C23—H232 | 109.5 | N12—C14—H143 | 109.5 |
H231—C23—H232 | 109.5 | C12—C14—H143 | 127.2 |
N221—C23—H233 | 109.5 | H141—C14—H143 | 109.5 |
H231—C23—H233 | 109.5 | H142—C14—H143 | 109.5 |
N21—C21—C22—N222 | −161.1 (5) | N11—C11—C12—C14 | 124.1 (12) |
N21—C21—C22—N221 | 161.7 (4) | C11—C12—N12—C13 | 102.2 (10) |
C21—C22—N221—C23 | 163.0 (4) | C14—C12—N12—C13 | −102.9 (11) |
C21—C22—N221—C24 | 38.6 (5) | C11—C12—N12—C14 | −154.9 (6) |
C21—C22—N222—C24 | −36.6 (9) | C13—N12—C14—C12 | 140.6 (6) |
C21—C22—N222—C23 | −163.7 (5) | C11—C12—C14—N12 | 63.5 (12) |
N11—C11—C12—N12 | 175.2 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H113···Cl1i | 0.89 | 2.82 | 3.628 (11) | 152 |
N11—H111···Cl4 | 0.89 | 2.83 | 3.421 (14) | 125 |
N11—H111···Cl6i | 0.89 | 2.66 | 3.013 (6) | 105 |
N11—H112···Cl6ii | 0.89 | 2.63 | 3.474 (6) | 160 |
N12—H121···Cl2 | 0.98 | 2.18 | 3.118 (5) | 160 |
N21—H213···Cl1iii | 0.89 | 2.35 | 3.237 (3) | 171 |
N21—H212···Cl2iv | 0.89 | 2.36 | 3.176 (3) | 152 |
N21—H211···Cl3v | 0.89 | 2.44 | 3.183 (3) | 142 |
N221—H221···Cl1vi | 0.98 | 2.57 | 3.379 (5) | 140 |
N221—H221···Cl4iii | 0.98 | 2.90 | 3.471 (5) | 118 |
N222—H222···Cl3 | 0.98 | 2.19 | 3.098 (11) | 154 |
C11—H114···Cl4ii | 0.97 | 2.81 | 3.595 (6) | 139 |
C11—H114···Cl4vii | 0.97 | 2.83 | 3.500 (7) | 127 |
C11—H115···Cl4 | 0.97 | 2.88 | 3.429 (7) | 117 |
C12—H122···Cl2vii | 0.97 | 2.83 | 3.673 (6) | 146 |
C13—H132···Cl6vi | 0.96 | 2.69 | 3.272 (8) | 120 |
C14—H141···Cl6 | 0.96 | 2.61 | 3.489 (8) | 152 |
C21—H215···Cl5iii | 0.97 | 2.87 | 3.667 (4) | 141 |
C22—H223···Cl3 | 0.97 | 2.84 | 3.535 (3) | 130 |
C22—H224···Cl4iii | 0.97 | 2.83 | 3.577 (3) | 134 |
C23—H232···Cl4iii | 0.96 | 2.88 | 3.541 (4) | 127 |
C24—H242···Cl3vi | 0.96 | 2.65 | 3.590 (4) | 166 |
C24—H243···Cl3 | 0.96 | 2.78 | 3.641 (4) | 150 |
Symmetry codes: (i) −x, −y, −z+1; (ii) x, −y, z−1/2; (iii) x, y+1, z; (iv) x, −y+1, z+1/2; (v) −x+1/2, y+1/2, −z+3/2; (vi) x, −y+1, z−1/2; (vii) −x, y, −z+1/2. |
(C4H14N2)3[BiCl6]2 | F(000) = 2104 |
Mr = 1113.88 | Dx = 2.194 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 27.5447 (3) Å | Cell parameters from 9666 reflections |
b = 10.14187 (11) Å | θ = 3.1–29.5° |
c = 12.38379 (14) Å | µ = 11.39 mm−1 |
β = 102.9055 (12)° | T = 100 K |
V = 3372.08 (7) Å3 | Plate, colourless |
Z = 4 | 0.25 × 0.16 × 0.09 mm |
Xcalibur diffractometer | 3182 reflections with I > 2σ(I) |
ω–scan | Rint = 0.014 |
Absorption correction: multi-scan CrysAlisPro 1.171.40.56a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | θmax = 26.0°, θmin = 3.0° |
Tmin = 0.25, Tmax = 1.00 | h = −33→33 |
10977 measured reflections | k = −8→12 |
3301 independent reflections | l = −15→15 |
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)] = 0.016 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.037 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0171P)2 + 9.7374P] where P = (Fo2 + 2Fc2)/3 |
3301 reflections | (Δ/σ)max = 0.004 |
188 parameters | Δρmax = 0.92 e Å−3 |
18 restraints | Δρmin = −0.88 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) | |
Bi1 | 0.12889 (2) | 0.19747 (2) | 0.59449 (2) | 0.01351 (4) | |
Cl1 | 0.14238 (3) | 0.08234 (7) | 0.79430 (6) | 0.02641 (17) | |
Cl2 | 0.12157 (3) | 0.32433 (7) | 0.39517 (6) | 0.02001 (14) | |
Cl3 | 0.18234 (3) | 0.40586 (7) | 0.68923 (5) | 0.01988 (14) | |
Cl4 | 0.07098 (3) | −0.00762 (7) | 0.50787 (6) | 0.02230 (15) | |
Cl5 | 0.21344 (3) | 0.08319 (7) | 0.56496 (6) | 0.02164 (15) | |
Cl6 | 0.04548 (4) | 0.31386 (11) | 0.63160 (10) | 0.0507 (3) | |
N21 | 0.20711 (10) | 0.8168 (3) | 0.8057 (2) | 0.0224 (6) | |
H211 | 0.2386 | 0.8298 | 0.8410 | 0.034* | |
H212 | 0.1930 | 0.7586 | 0.8431 | 0.034* | |
H213 | 0.1906 | 0.8927 | 0.8007 | 0.034* | |
C21 | 0.20562 (12) | 0.7652 (3) | 0.6924 (2) | 0.0219 (6) | |
H214 | 0.2250 | 0.6846 | 0.6976 | 0.026* | |
H215 | 0.2203 | 0.8292 | 0.6511 | 0.026* | |
C22 | 0.15256 (12) | 0.7379 (3) | 0.6325 (2) | 0.0211 (6) | |
H223 | 0.1413 | 0.6579 | 0.6622 | 0.025* | |
H224 | 0.1316 | 0.8097 | 0.6469 | 0.025* | |
N221 | 0.14607 (13) | 0.7228 (4) | 0.5100 (3) | 0.0239 (9) | 0.813 (7) |
H221 | 0.1467 | 0.8114 | 0.4788 | 0.029* | 0.813 (7) |
N222 | 0.1501 (5) | 0.6447 (16) | 0.5366 (11) | 0.019 (2) | 0.187 (7) |
H222 | 0.1502 | 0.5558 | 0.5677 | 0.023* | 0.187 (7) |
C23 | 0.09665 (13) | 0.6636 (3) | 0.4595 (3) | 0.0291 (7) | |
H231 | 0.0923 | 0.6608 | 0.3804 | 0.044* | |
H232 | 0.0707 | 0.7162 | 0.4782 | 0.044* | |
H233 | 0.0951 | 0.5757 | 0.4873 | 0.044* | |
C24 | 0.18666 (13) | 0.6445 (3) | 0.4768 (3) | 0.0283 (7) | |
H241 | 0.2183 | 0.6846 | 0.5074 | 0.042* | |
H242 | 0.1812 | 0.6428 | 0.3974 | 0.042* | |
H243 | 0.1864 | 0.5560 | 0.5042 | 0.042* | |
N11 | −0.0105 (2) | −0.0788 (5) | 0.2663 (5) | 0.0209 (12) | 0.5 |
H111 | −0.0081 | −0.0832 | 0.3391 | 0.031* | 0.5 |
H112 | 0.0043 | −0.1486 | 0.2444 | 0.031* | 0.5 |
H113 | −0.0425 | −0.0779 | 0.2316 | 0.031* | 0.5 |
C11 | 0.0139 (2) | 0.0429 (5) | 0.2395 (5) | 0.0150 (12) | 0.5 |
H114 | 0.0118 | 0.0477 | 0.1604 | 0.018* | 0.5 |
H115 | 0.0488 | 0.0427 | 0.2772 | 0.018* | 0.5 |
C12 | −0.0123 (2) | 0.1610 (6) | 0.2767 (5) | 0.0157 (11) | 0.5 |
H122 | −0.0465 | 0.1643 | 0.2347 | 0.019* | 0.5 |
H123 | −0.0127 | 0.1514 | 0.3544 | 0.019* | 0.5 |
N12 | 0.01358 (16) | 0.2863 (4) | 0.2603 (5) | 0.0165 (12) | 0.5 |
H121 | 0.0491 | 0.2752 | 0.2933 | 0.020* | 0.5 |
C13 | 0.0079 (2) | 0.4019 (6) | 0.1910 (5) | 0.0229 (13) | 0.5 |
H131 | −0.0035 | 0.3764 | 0.1149 | 0.034* | 0.5 |
H132 | 0.0394 | 0.4461 | 0.2003 | 0.034* | 0.5 |
H133 | −0.0159 | 0.4603 | 0.2117 | 0.034* | 0.5 |
C14 | −0.0143 (2) | 0.3129 (6) | 0.3582 (5) | 0.0205 (13) | 0.5 |
H141 | 0.0099 | 0.3307 | 0.4254 | 0.031* | 0.5 |
H142 | −0.0334 | 0.2367 | 0.3682 | 0.031* | 0.5 |
H143 | −0.0360 | 0.3875 | 0.3397 | 0.031* | 0.5 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Bi1 | 0.01258 (6) | 0.01472 (6) | 0.01197 (6) | 0.00171 (4) | 0.00004 (4) | 0.00031 (4) |
Cl1 | 0.0470 (5) | 0.0187 (3) | 0.0164 (3) | 0.0031 (3) | 0.0132 (3) | 0.0028 (3) |
Cl2 | 0.0195 (4) | 0.0206 (3) | 0.0173 (3) | −0.0019 (3) | −0.0015 (3) | 0.0037 (3) |
Cl3 | 0.0263 (4) | 0.0170 (3) | 0.0140 (3) | −0.0029 (3) | −0.0003 (3) | 0.0009 (3) |
Cl4 | 0.0234 (4) | 0.0242 (4) | 0.0166 (3) | −0.0058 (3) | −0.0015 (3) | 0.0007 (3) |
Cl5 | 0.0169 (3) | 0.0256 (4) | 0.0214 (3) | 0.0031 (3) | 0.0022 (3) | −0.0008 (3) |
Cl6 | 0.0305 (5) | 0.0552 (6) | 0.0601 (7) | 0.0248 (4) | −0.0031 (5) | −0.0199 (5) |
N21 | 0.0212 (14) | 0.0259 (14) | 0.0172 (13) | 0.0045 (11) | −0.0019 (11) | −0.0050 (10) |
C21 | 0.0238 (16) | 0.0254 (16) | 0.0155 (14) | −0.0024 (13) | 0.0022 (12) | −0.0069 (12) |
C22 | 0.0262 (17) | 0.0186 (14) | 0.0148 (14) | 0.0049 (12) | −0.0031 (12) | −0.0027 (12) |
N221 | 0.0330 (18) | 0.0205 (19) | 0.0147 (15) | −0.0024 (14) | −0.0019 (13) | 0.0017 (13) |
N222 | 0.023 (4) | 0.018 (4) | 0.014 (4) | −0.001 (3) | −0.001 (3) | 0.000 (3) |
C23 | 0.034 (2) | 0.0240 (16) | 0.0223 (16) | −0.0019 (14) | −0.0087 (14) | −0.0028 (13) |
C24 | 0.038 (2) | 0.0319 (18) | 0.0145 (15) | −0.0022 (15) | 0.0062 (14) | −0.0010 (13) |
N11 | 0.019 (4) | 0.019 (2) | 0.025 (4) | 0.002 (2) | 0.003 (2) | 0.001 (2) |
C11 | 0.017 (3) | 0.018 (3) | 0.010 (3) | 0.001 (2) | 0.003 (2) | 0.001 (2) |
C12 | 0.012 (3) | 0.019 (3) | 0.015 (3) | 0.003 (2) | 0.003 (2) | 0.002 (2) |
N12 | 0.013 (3) | 0.018 (2) | 0.017 (3) | 0.0012 (16) | 0.002 (3) | −0.004 (2) |
C13 | 0.020 (3) | 0.023 (3) | 0.025 (3) | −0.005 (3) | 0.003 (3) | 0.005 (3) |
C14 | 0.024 (3) | 0.020 (3) | 0.016 (3) | 0.000 (2) | 0.004 (2) | 0.000 (2) |
Bi1—Cl1 | 2.6858 (7) | C23—H233 | 0.9600 |
Bi1—Cl3 | 2.6906 (7) | C24—H241 | 0.9600 |
Bi1—Cl4 | 2.6939 (7) | C24—H242 | 0.9600 |
Bi1—Cl5 | 2.6985 (7) | C24—H243 | 0.9600 |
Bi1—Cl6 | 2.7120 (9) | N11—C11 | 1.478 (7) |
Bi1—Cl2 | 2.7507 (7) | N11—H111 | 0.8900 |
N21—C21 | 1.489 (4) | N11—H112 | 0.8900 |
N21—H211 | 0.8900 | N11—H113 | 0.8900 |
N21—H212 | 0.8900 | C11—C12 | 1.521 (7) |
N21—H213 | 0.8900 | C11—H114 | 0.9700 |
C21—C22 | 1.510 (4) | C11—H115 | 0.9700 |
C21—H214 | 0.9700 | C12—N12 | 1.494 (7) |
C21—H215 | 0.9700 | C12—C14 | 1.849 (8) |
C22—N221 | 1.495 (4) | C12—H122 | 0.9700 |
C22—N222 | 1.508 (13) | C12—H123 | 0.9700 |
C22—H223 | 0.9700 | N12—C13 | 1.440 (8) |
C22—H224 | 0.9700 | N12—C14 | 1.596 (8) |
N221—C23 | 1.491 (5) | N12—H121 | 0.9800 |
N221—C24 | 1.502 (5) | C13—H131 | 0.9600 |
N221—H221 | 0.9800 | C13—H132 | 0.9600 |
N222—C24 | 1.377 (14) | C13—H133 | 0.9600 |
N222—C23 | 1.577 (14) | C14—H141 | 0.9600 |
N222—H222 | 0.9800 | C14—H142 | 0.9600 |
C23—H231 | 0.9600 | C14—H143 | 0.9600 |
C23—H232 | 0.9600 | ||
Cl1—Bi1—Cl3 | 89.43 (2) | H232—C23—H233 | 109.5 |
Cl1—Bi1—Cl4 | 88.79 (2) | N221—C24—H241 | 109.5 |
Cl3—Bi1—Cl4 | 176.20 (2) | N221—C24—H242 | 109.5 |
Cl1—Bi1—Cl5 | 89.55 (2) | H241—C24—H242 | 109.5 |
Cl3—Bi1—Cl5 | 89.53 (2) | N221—C24—H243 | 109.5 |
Cl4—Bi1—Cl5 | 93.82 (2) | H241—C24—H243 | 109.5 |
Cl1—Bi1—Cl6 | 88.92 (3) | H242—C24—H243 | 109.5 |
Cl3—Bi1—Cl6 | 89.19 (3) | C11—N11—H111 | 109.5 |
Cl4—Bi1—Cl6 | 87.41 (3) | C11—N11—H112 | 109.5 |
Cl5—Bi1—Cl6 | 178.02 (3) | H111—N11—H112 | 109.5 |
Cl1—Bi1—Cl2 | 175.87 (2) | C11—N11—H113 | 109.5 |
Cl3—Bi1—Cl2 | 86.97 (2) | H111—N11—H113 | 109.5 |
Cl4—Bi1—Cl2 | 94.91 (2) | H112—N11—H113 | 109.5 |
Cl5—Bi1—Cl2 | 88.38 (2) | N11—C11—C12 | 108.7 (4) |
Cl6—Bi1—Cl2 | 93.06 (3) | N11—C11—H114 | 110.0 |
C21—N21—H211 | 109.5 | C12—C11—H114 | 110.0 |
C21—N21—H212 | 109.5 | N11—C11—H115 | 110.0 |
H211—N21—H212 | 109.5 | C12—C11—H115 | 110.0 |
C21—N21—H213 | 109.5 | H114—C11—H115 | 108.3 |
H211—N21—H213 | 109.5 | N12—C12—C11 | 110.9 (4) |
H212—N21—H213 | 109.5 | N12—C12—C14 | 55.8 (3) |
N21—C21—C22 | 110.3 (3) | C11—C12—C14 | 153.5 (5) |
N21—C21—H214 | 109.6 | N12—C12—H122 | 109.5 |
C22—C21—H214 | 109.6 | C11—C12—H122 | 109.5 |
N21—C21—H215 | 109.6 | C14—C12—H122 | 96.9 |
C22—C21—H215 | 109.6 | N12—C12—H123 | 109.5 |
H214—C21—H215 | 108.1 | C11—C12—H123 | 109.5 |
N221—C22—C21 | 113.7 (3) | C14—C12—H123 | 62.3 |
N222—C22—C21 | 111.7 (6) | H122—C12—H123 | 108.1 |
N221—C22—H223 | 108.8 | C13—N12—C12 | 141.5 (5) |
C21—C22—H223 | 108.8 | C13—N12—C14 | 107.9 (4) |
N221—C22—H224 | 108.8 | C12—N12—C14 | 73.5 (4) |
C21—C22—H224 | 108.8 | C13—N12—H121 | 107.9 |
H223—C22—H224 | 107.7 | C12—N12—H121 | 107.9 |
C23—N221—C22 | 111.0 (3) | C14—N12—H121 | 107.9 |
C23—N221—C24 | 109.7 (3) | N12—C13—H131 | 109.5 |
C22—N221—C24 | 113.9 (3) | N12—C13—H132 | 109.5 |
C23—N221—H221 | 107.3 | H131—C13—H132 | 109.5 |
C22—N221—H221 | 107.3 | N12—C13—H133 | 109.5 |
C24—N221—H221 | 107.3 | H131—C13—H133 | 109.5 |
C24—N222—C22 | 121.0 (10) | H132—C13—H133 | 109.5 |
C24—N222—C23 | 111.7 (9) | N12—C14—C12 | 50.7 (3) |
C22—N222—C23 | 105.8 (9) | N12—C14—H141 | 109.5 |
C24—N222—H222 | 105.7 | C12—C14—H141 | 122.0 |
C22—N222—H222 | 105.7 | N12—C14—H142 | 109.5 |
C23—N222—H222 | 105.7 | C12—C14—H142 | 58.9 |
N221—C23—H231 | 109.5 | H141—C14—H142 | 109.5 |
N221—C23—H232 | 109.5 | N12—C14—H143 | 109.5 |
H231—C23—H232 | 109.5 | C12—C14—H143 | 128.3 |
N221—C23—H233 | 109.5 | H141—C14—H143 | 109.5 |
H231—C23—H233 | 109.5 | H142—C14—H143 | 109.5 |
N21—C21—C22—N221 | 163.7 (3) | N11—C11—C12—C14 | 120.9 (10) |
N21—C21—C22—N222 | −160.4 (7) | C11—C12—N12—C13 | 107.8 (8) |
C21—C22—N221—C23 | 165.8 (3) | C14—C12—N12—C13 | −98.2 (8) |
C21—C22—N221—C24 | 41.3 (4) | C11—C12—N12—C14 | −154.0 (5) |
C21—C22—N222—C24 | −32.7 (14) | C13—N12—C14—C12 | 139.6 (5) |
C21—C22—N222—C23 | −160.9 (6) | C11—C12—C14—N12 | 66.6 (10) |
N11—C11—C12—N12 | 175.2 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H113···Cl1i | 0.89 | 2.70 | 3.541 (5) | 159 |
N11—H111···Cl4 | 0.89 | 2.77 | 3.392 (7) | 128 |
N11—H111···Cl6i | 0.89 | 2.61 | 2.959 (5) | 104 |
N11—H112···Cl6ii | 0.89 | 2.60 | 3.463 (5) | 164 |
N12—H121···Cl2 | 0.98 | 2.17 | 3.093 (4) | 157 |
N21—H213···Cl1iii | 0.89 | 2.33 | 3.216 (3) | 175 |
N21—H212···Cl2iv | 0.89 | 2.36 | 3.161 (3) | 150 |
N21—H211···Cl3v | 0.89 | 2.42 | 3.163 (3) | 142 |
N221—H221···Cl1vi | 0.98 | 2.51 | 3.307 (4) | 139 |
N221—H221···Cl4iii | 0.98 | 2.86 | 3.425 (4) | 118 |
N222—H222···Cl3 | 0.98 | 2.18 | 3.079 (17) | 151 |
C11—H114···Cl4ii | 0.97 | 2.79 | 3.584 (5) | 140 |
C11—H114···Cl4vii | 0.97 | 2.78 | 3.451 (6) | 127 |
C11—H115···Cl4 | 0.97 | 2.83 | 3.383 (6) | 117 |
C12—H122···Cl2vii | 0.97 | 2.83 | 3.671 (6) | 145 |
C13—H132···Cl6vi | 0.96 | 2.60 | 3.203 (6) | 121 |
C14—H141···Cl6 | 0.96 | 2.53 | 3.419 (6) | 154 |
C21—H215···Cl5iii | 0.97 | 2.78 | 3.619 (3) | 145 |
C22—H223···Cl3 | 0.97 | 2.78 | 3.500 (3) | 131 |
C22—H224···Cl4iii | 0.97 | 2.81 | 3.542 (3) | 133 |
C23—H232···Cl4iii | 0.96 | 2.82 | 3.488 (3) | 127 |
C24—H242···Cl3vi | 0.96 | 2.63 | 3.573 (3) | 166 |
C24—H243···Cl3 | 0.96 | 2.77 | 3.596 (3) | 144 |
Symmetry codes: (i) −x, −y, −z+1; (ii) x, −y, z−1/2; (iii) x, y+1, z; (iv) x, −y+1, z+1/2; (v) −x+1/2, y+1/2, −z+3/2; (vi) x, −y+1, z−1/2; (vii) −x, y, −z+1/2. |
(C4H14N2)[BiCl5] | Dx = 2.442 Mg m−3 |
Mr = 476.40 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 8285 reflections |
a = 7.60312 (9) Å | θ = 3.1–29.7° |
b = 12.50404 (14) Å | µ = 14.60 mm−1 |
c = 13.63023 (15) Å | T = 295 K |
V = 1295.82 (3) Å3 | Pillar, colourless |
Z = 4 | 0.35 × 0.23 × 0.13 mm |
F(000) = 880 |
Xcalibur diffractometer | 2514 reflections with I > 2σ(I) |
ω–scan | Rint = 0.012 |
Absorption correction: analytical CrysAlisPro 1.171.40.56a (Rigaku Oxford Diffraction, 2019) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | θmax = 26.0°, θmin = 3.1° |
Tmin = 0.06, Tmax = 0.22 | h = −9→5 |
8742 measured reflections | k = −15→15 |
2545 independent reflections | l = −16→16 |
Refinement on F2 | Hydrogen site location: difference Fourier map |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.010 | w = 1/[σ2(Fo2) + (0.0097P)2 + 0.4838P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.024 | (Δ/σ)max = 0.001 |
S = 1.14 | Δρmax = 0.46 e Å−3 |
2545 reflections | Δρmin = −0.31 e Å−3 |
113 parameters | Extinction correction: SHELXL-2014/7 (Sheldrick 2014, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.00133 (10) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack x determined using 1035 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.031 (2) |
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 | ||
Bi1 | 0.18597 (2) | 0.39389 (2) | 0.06540 (2) | 0.02607 (5) | |
Cl1 | 0.48961 (14) | 0.47531 (10) | 0.10365 (9) | 0.0464 (3) | |
Cl2 | −0.13638 (14) | 0.29292 (10) | 0.00821 (9) | 0.0482 (3) | |
Cl3 | 0.02510 (16) | 0.56208 (9) | 0.12695 (8) | 0.0448 (3) | |
Cl4 | 0.19903 (16) | 0.48399 (9) | −0.11328 (8) | 0.0456 (3) | |
Cl5 | 0.15790 (18) | 0.29450 (9) | 0.24127 (8) | 0.0482 (3) | |
N1 | 0.8915 (5) | 0.5624 (3) | 0.3614 (3) | 0.0459 (10) | |
H11 | 0.9031 | 0.6206 | 0.3244 | 0.069* | |
H12 | 0.9936 | 0.5278 | 0.3641 | 0.069* | |
H13 | 0.8591 | 0.5814 | 0.4217 | 0.069* | |
N2 | 0.5883 (5) | 0.3251 (3) | 0.3396 (3) | 0.0430 (9) | |
H21 | 0.4903 | 0.3708 | 0.3192 | 0.052* | |
C1 | 0.7568 (6) | 0.4921 (5) | 0.3186 (4) | 0.0530 (12) | |
H14 | 0.7936 | 0.4696 | 0.2537 | 0.064* | |
H15 | 0.6471 | 0.5311 | 0.3121 | 0.064* | |
C2 | 0.7293 (6) | 0.3968 (4) | 0.3816 (4) | 0.0494 (11) | |
H22 | 0.6952 | 0.4196 | 0.4469 | 0.059* | |
H23 | 0.8385 | 0.3572 | 0.3869 | 0.059* | |
C3 | 0.6432 (8) | 0.2614 (5) | 0.2529 (4) | 0.0603 (15) | |
H31 | 0.6803 | 0.3087 | 0.2014 | 0.090* | |
H32 | 0.5459 | 0.2191 | 0.2304 | 0.090* | |
H33 | 0.7388 | 0.2152 | 0.2707 | 0.090* | |
C4 | 0.5220 (9) | 0.2529 (4) | 0.4179 (4) | 0.0667 (16) | |
H41 | 0.4759 | 0.2948 | 0.4710 | 0.100* | |
H42 | 0.6166 | 0.2090 | 0.4415 | 0.100* | |
H43 | 0.4307 | 0.2081 | 0.3918 | 0.100* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Bi1 | 0.02598 (7) | 0.02497 (7) | 0.02727 (7) | −0.00014 (6) | 0.00064 (6) | −0.00007 (6) |
Cl1 | 0.0341 (5) | 0.0450 (6) | 0.0601 (7) | −0.0077 (5) | −0.0095 (5) | −0.0042 (5) |
Cl2 | 0.0390 (6) | 0.0489 (7) | 0.0568 (7) | −0.0115 (5) | −0.0036 (5) | −0.0088 (5) |
Cl3 | 0.0535 (7) | 0.0391 (6) | 0.0418 (6) | 0.0107 (5) | 0.0081 (5) | −0.0064 (5) |
Cl4 | 0.0427 (6) | 0.0550 (6) | 0.0390 (5) | 0.0119 (6) | 0.0061 (5) | 0.0150 (5) |
Cl5 | 0.0643 (8) | 0.0461 (6) | 0.0342 (5) | −0.0105 (6) | 0.0002 (5) | 0.0062 (4) |
N1 | 0.040 (2) | 0.050 (2) | 0.048 (2) | −0.0048 (18) | −0.0029 (18) | 0.0072 (19) |
N2 | 0.040 (2) | 0.0320 (19) | 0.057 (2) | 0.0057 (16) | −0.0008 (18) | −0.0030 (18) |
C1 | 0.038 (2) | 0.062 (3) | 0.060 (3) | −0.009 (2) | −0.007 (2) | 0.012 (3) |
C2 | 0.047 (3) | 0.049 (3) | 0.052 (3) | 0.002 (2) | −0.003 (2) | 0.005 (3) |
C3 | 0.064 (4) | 0.066 (4) | 0.051 (3) | 0.018 (3) | 0.002 (3) | −0.011 (3) |
C4 | 0.089 (4) | 0.047 (3) | 0.064 (4) | −0.004 (3) | 0.014 (3) | −0.002 (3) |
Bi1—Cl3 | 2.5735 (11) | N2—C2 | 1.510 (6) |
Bi1—Cl1 | 2.5764 (11) | N2—H21 | 0.9800 |
Bi1—Cl4 | 2.6853 (10) | C1—C2 | 1.483 (7) |
Bi1—Cl5 | 2.7085 (11) | C1—H14 | 0.9700 |
Bi1—Cl2 | 2.8650 (11) | C1—H15 | 0.9700 |
Bi1—Cl2i | 2.8788 (11) | C2—H22 | 0.9700 |
Cl2—Bi1ii | 2.8787 (11) | C2—H23 | 0.9700 |
N1—C1 | 1.470 (6) | C3—H31 | 0.9600 |
N1—H11 | 0.8900 | C3—H32 | 0.9600 |
N1—H12 | 0.8900 | C3—H33 | 0.9600 |
N1—H13 | 0.8900 | C4—H41 | 0.9600 |
N2—C3 | 1.485 (6) | C4—H42 | 0.9600 |
N2—C4 | 1.486 (6) | C4—H43 | 0.9600 |
Cl3—Bi1—Cl1 | 92.12 (4) | C4—N2—H21 | 107.5 |
Cl3—Bi1—Cl4 | 88.30 (4) | C2—N2—H21 | 107.5 |
Cl1—Bi1—Cl4 | 89.12 (4) | N1—C1—C2 | 110.4 (4) |
Cl3—Bi1—Cl5 | 92.81 (4) | N1—C1—H14 | 109.6 |
Cl1—Bi1—Cl5 | 94.18 (4) | C2—C1—H14 | 109.6 |
Cl4—Bi1—Cl5 | 176.48 (4) | N1—C1—H15 | 109.6 |
Cl3—Bi1—Cl2 | 92.42 (4) | C2—C1—H15 | 109.6 |
Cl1—Bi1—Cl2 | 174.69 (4) | H14—C1—H15 | 108.1 |
Cl4—Bi1—Cl2 | 88.27 (4) | C1—C2—N2 | 111.0 (4) |
Cl5—Bi1—Cl2 | 88.35 (4) | C1—C2—H22 | 109.4 |
Cl3—Bi1—Cl2i | 178.62 (4) | N2—C2—H22 | 109.4 |
Cl1—Bi1—Cl2i | 88.33 (4) | C1—C2—H23 | 109.4 |
Cl4—Bi1—Cl2i | 90.40 (4) | N2—C2—H23 | 109.4 |
Cl5—Bi1—Cl2i | 88.46 (4) | H22—C2—H23 | 108.0 |
Cl2—Bi1—Cl2i | 87.077 (12) | N2—C3—H31 | 109.5 |
Bi1—Cl2—Bi1ii | 148.62 (5) | N2—C3—H32 | 109.5 |
C1—N1—H11 | 109.5 | H31—C3—H32 | 109.5 |
C1—N1—H12 | 109.5 | N2—C3—H33 | 109.5 |
H11—N1—H12 | 109.5 | H31—C3—H33 | 109.5 |
C1—N1—H13 | 109.5 | H32—C3—H33 | 109.5 |
H11—N1—H13 | 109.5 | N2—C4—H41 | 109.5 |
H12—N1—H13 | 109.5 | N2—C4—H42 | 109.5 |
C3—N2—C4 | 109.9 (4) | H41—C4—H42 | 109.5 |
C3—N2—C2 | 114.9 (4) | N2—C4—H43 | 109.5 |
C4—N2—C2 | 109.2 (4) | H41—C4—H43 | 109.5 |
C3—N2—H21 | 107.5 | H42—C4—H43 | 109.5 |
N1—C1—C2—N2 | 178.8 (4) | C4—N2—C2—C1 | −161.0 (4) |
C3—N2—C2—C1 | 74.9 (5) |
Symmetry codes: (i) x+1/2, −y+1/2, −z; (ii) x−1/2, −y+1/2, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H13···Cl1iii | 0.89 | 2.82 | 3.455 (4) | 129 |
N1—H13···Cl2iv | 0.89 | 2.59 | 3.322 (4) | 140 |
N1—H12···Cl4iii | 0.89 | 2.36 | 3.186 (4) | 154 |
N1—H11···Cl5v | 0.89 | 2.40 | 3.243 (4) | 159 |
N2—H21···Cl4iv | 0.98 | 2.49 | 3.299 (4) | 139 |
N2—H21···Cl5 | 0.98 | 2.90 | 3.557 (4) | 125 |
C1—H14···Cl3vi | 0.97 | 2.72 | 3.428 (6) | 130 |
C1—H15···Cl4iv | 0.97 | 2.83 | 3.600 (5) | 137 |
C4—H41···Cl3iv | 0.96 | 2.78 | 3.688 (6) | 158 |
Symmetry codes: (iii) −x+3/2, −y+1, z+1/2; (iv) −x+1/2, −y+1, z+1/2; (v) −x+1, y+1/2, −z+1/2; (vi) x+1, y, z. |
(C5H14N3)3[Bi2Cl9] | F(000) = 2056 |
Mr = 1085.59 | Dx = 2.024 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.57031 (17) Å | Cell parameters from 12505 reflections |
b = 29.2063 (4) Å | θ = 3.0–29.5° |
c = 12.04367 (19) Å | µ = 10.56 mm−1 |
β = 106.6342 (17)° | T = 295 K |
V = 3562.52 (10) Å3 | Pillar, colourless |
Z = 4 | 0.22 × 0.20 × 0.19 mm |
Xcalibur diffractometer | 6102 reflections with I > 2σ(I) |
ω–scan | Rint = 0.023 |
Absorption correction: analytical CrysAlisPro 1.171.40.56a (Rigaku Oxford Diffraction, 2019) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | θmax = 26.0°, θmin = 3.1° |
Tmin = 0.21, Tmax = 0.27 | h = −13→13 |
23916 measured reflections | k = −36→36 |
6979 independent reflections | l = −14→11 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.018 | H-atom parameters constrained |
wR(F2) = 0.037 | w = 1/[σ2(Fo2) + (0.0127P)2 + 1.928P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.003 |
6979 reflections | Δρmax = 0.70 e Å−3 |
329 parameters | Δρmin = −0.63 e Å−3 |
12 restraints | Extinction correction: SHELXL-2014/7 (Sheldrick 2014, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00220 (4) |
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 | ||
Bi1 | 0.17900 (2) | 0.40340 (2) | 0.29526 (2) | 0.03424 (4) | |
Bi2 | 0.25329 (2) | 0.34809 (2) | 0.60555 (2) | 0.03534 (4) | |
Cl1 | −0.05278 (9) | 0.39190 (4) | 0.16377 (8) | 0.0602 (2) | |
Cl2 | 0.42743 (8) | 0.40316 (3) | 0.50121 (8) | 0.0504 (2) | |
Cl3 | 0.08193 (9) | 0.30002 (4) | 0.66543 (9) | 0.0613 (3) | |
Cl4 | 0.29023 (10) | 0.38508 (3) | 0.13968 (8) | 0.0580 (2) | |
Cl5 | 0.06958 (8) | 0.41757 (3) | 0.49445 (7) | 0.0459 (2) | |
Cl6 | 0.42799 (9) | 0.28379 (3) | 0.68143 (8) | 0.0512 (2) | |
Cl7 | 0.16839 (10) | 0.49020 (3) | 0.24346 (9) | 0.0576 (2) | |
Cl8 | 0.18885 (10) | 0.31149 (3) | 0.37320 (8) | 0.0530 (2) | |
Cl9 | 0.33459 (9) | 0.39077 (3) | 0.79966 (8) | 0.0556 (2) | |
N11 | 0.5794 (3) | 0.30533 (12) | 0.4881 (3) | 0.0741 (11) | |
H111 | 0.5318 | 0.3272 | 0.4501 | 0.089* | |
H112 | 0.5606 | 0.2934 | 0.5467 | 0.089* | |
C11 | 0.6817 (4) | 0.29006 (12) | 0.4566 (3) | 0.0488 (9) | |
N12 | 0.7070 (3) | 0.30919 (11) | 0.3668 (3) | 0.0576 (8) | |
C12 | 0.8468 (4) | 0.31255 (15) | 0.3587 (4) | 0.0720 (12) | |
H121 | 0.9072 | 0.3023 | 0.4300 | 0.108* | |
H122 | 0.8661 | 0.3438 | 0.3447 | 0.108* | |
H123 | 0.8559 | 0.2937 | 0.2961 | 0.108* | |
C13 | 0.6082 (6) | 0.33624 (19) | 0.2834 (4) | 0.1047 (19) | |
H131 | 0.5216 | 0.3273 | 0.2858 | 0.157* | |
H132 | 0.6162 | 0.3311 | 0.2070 | 0.157* | |
H133 | 0.6217 | 0.3681 | 0.3023 | 0.157* | |
N13 | 0.7567 (3) | 0.25636 (9) | 0.5145 (2) | 0.0476 (7) | |
C14 | 0.8263 (4) | 0.22276 (14) | 0.4633 (3) | 0.0680 (11) | |
H141 | 0.8018 | 0.2268 | 0.3808 | 0.102* | |
H142 | 0.8030 | 0.1924 | 0.4810 | 0.102* | |
H143 | 0.9199 | 0.2270 | 0.4946 | 0.102* | |
C15 | 0.7549 (4) | 0.24619 (15) | 0.6314 (3) | 0.0672 (11) | |
H151 | 0.7441 | 0.2741 | 0.6700 | 0.101* | |
H152 | 0.8366 | 0.2319 | 0.6727 | 0.101* | |
H153 | 0.6828 | 0.2259 | 0.6294 | 0.101* | |
N21 | 0.6443 (3) | 0.37057 (14) | 0.7702 (3) | 0.0802 (11) | |
H211 | 0.5818 | 0.3592 | 0.7944 | 0.096* | |
H212 | 0.6261 | 0.3897 | 0.7135 | 0.096* | |
C21 | 0.7679 (3) | 0.35864 (11) | 0.8202 (3) | 0.0419 (8) | |
N22 | 0.8632 (3) | 0.37592 (10) | 0.7807 (2) | 0.0446 (7) | |
C22 | 0.9892 (4) | 0.38961 (15) | 0.8581 (4) | 0.0671 (11) | |
H221 | 0.9888 | 0.3849 | 0.9368 | 0.101* | |
H222 | 1.0043 | 0.4214 | 0.8463 | 0.101* | |
H223 | 1.0582 | 0.3716 | 0.8424 | 0.101* | |
C23 | 0.8335 (4) | 0.39353 (13) | 0.6624 (3) | 0.0611 (10) | |
H231 | 0.7636 | 0.3758 | 0.6125 | 0.092* | |
H232 | 0.9108 | 0.3914 | 0.6361 | 0.092* | |
H233 | 0.8065 | 0.4250 | 0.6611 | 0.092* | |
N23 | 0.7935 (3) | 0.32924 (10) | 0.9072 (2) | 0.0478 (7) | |
C24 | 0.9098 (4) | 0.29955 (14) | 0.9337 (4) | 0.0715 (12) | |
H241 | 0.9525 | 0.3023 | 0.8735 | 0.107* | |
H242 | 0.8832 | 0.2684 | 0.9385 | 0.107* | |
H243 | 0.9700 | 0.3085 | 1.0064 | 0.107* | |
C25 | 0.6966 (4) | 0.31749 (15) | 0.9673 (4) | 0.0714 (12) | |
H251 | 0.6401 | 0.3433 | 0.9664 | 0.107* | |
H252 | 0.7412 | 0.3094 | 1.0461 | 0.107* | |
H253 | 0.6446 | 0.2920 | 0.9292 | 0.107* | |
N31 | 0.1341 (3) | 0.49680 (10) | 0.7121 (2) | 0.0484 (7) | |
H311 | 0.1071 | 0.4920 | 0.6387 | 0.058* | |
H312 | 0.0814 | 0.4927 | 0.7540 | 0.058* | |
C31 | 0.2564 (3) | 0.51056 (11) | 0.7607 (3) | 0.0392 (8) | |
N32 | 0.2977 (3) | 0.51754 (9) | 0.8753 (2) | 0.0452 (7) | |
C32 | 0.3894 (4) | 0.55436 (13) | 0.9254 (3) | 0.0640 (11) | |
H321 | 0.4101 | 0.5713 | 0.8645 | 0.096* | |
H322 | 0.4688 | 0.5416 | 0.9758 | 0.096* | |
H323 | 0.3496 | 0.5745 | 0.9688 | 0.096* | |
C33 | 0.2250 (4) | 0.49829 (14) | 0.9508 (3) | 0.0634 (11) | |
H331 | 0.1917 | 0.4686 | 0.9227 | 0.095* | |
H332 | 0.1527 | 0.5181 | 0.9513 | 0.095* | |
H333 | 0.2830 | 0.4955 | 1.0281 | 0.095* | |
N33 | 0.3376 (3) | 0.51693 (10) | 0.6959 (2) | 0.0458 (7) | |
C34 | 0.4786 (3) | 0.50633 (14) | 0.7376 (4) | 0.0624 (11) | |
H341 | 0.4975 | 0.4918 | 0.8121 | 0.094* | |
H342 | 0.5287 | 0.5341 | 0.7443 | 0.094* | |
H343 | 0.5021 | 0.4861 | 0.6839 | 0.094* | |
C35 | 0.2861 (4) | 0.52309 (14) | 0.5701 (3) | 0.0621 (11) | |
H351 | 0.2019 | 0.5381 | 0.5523 | 0.093* | |
H352 | 0.2762 | 0.4937 | 0.5328 | 0.093* | |
H353 | 0.3465 | 0.5415 | 0.5430 | 0.093* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Bi1 | 0.03585 (7) | 0.03608 (7) | 0.03089 (7) | 0.00278 (5) | 0.00970 (5) | 0.00190 (5) |
Bi2 | 0.03480 (7) | 0.03907 (7) | 0.03305 (7) | 0.00171 (5) | 0.01113 (5) | 0.00272 (5) |
Cl1 | 0.0462 (5) | 0.0757 (7) | 0.0509 (5) | −0.0061 (5) | 0.0014 (4) | −0.0017 (5) |
Cl2 | 0.0390 (5) | 0.0501 (5) | 0.0618 (6) | −0.0023 (4) | 0.0140 (4) | 0.0013 (4) |
Cl3 | 0.0496 (5) | 0.0743 (7) | 0.0621 (6) | −0.0163 (5) | 0.0198 (5) | 0.0056 (5) |
Cl4 | 0.0716 (6) | 0.0575 (6) | 0.0559 (6) | 0.0088 (5) | 0.0360 (5) | −0.0016 (4) |
Cl5 | 0.0429 (5) | 0.0522 (5) | 0.0447 (5) | 0.0077 (4) | 0.0155 (4) | −0.0008 (4) |
Cl6 | 0.0536 (5) | 0.0510 (5) | 0.0525 (5) | 0.0146 (4) | 0.0209 (4) | 0.0092 (4) |
Cl7 | 0.0610 (6) | 0.0413 (5) | 0.0782 (7) | 0.0058 (4) | 0.0323 (5) | 0.0063 (4) |
Cl8 | 0.0672 (6) | 0.0410 (5) | 0.0512 (5) | −0.0001 (4) | 0.0177 (5) | −0.0050 (4) |
Cl9 | 0.0560 (6) | 0.0610 (6) | 0.0507 (5) | −0.0012 (4) | 0.0168 (4) | −0.0142 (4) |
N11 | 0.063 (2) | 0.073 (2) | 0.101 (3) | 0.0215 (18) | 0.049 (2) | 0.019 (2) |
C11 | 0.0487 (12) | 0.0488 (12) | 0.0495 (12) | −0.0004 (9) | 0.0147 (9) | −0.0021 (9) |
N12 | 0.060 (2) | 0.063 (2) | 0.0490 (18) | −0.0119 (16) | 0.0153 (16) | 0.0133 (15) |
C12 | 0.073 (3) | 0.089 (3) | 0.065 (3) | −0.024 (2) | 0.039 (2) | 0.000 (2) |
C13 | 0.114 (5) | 0.123 (5) | 0.079 (3) | 0.049 (4) | 0.029 (3) | 0.045 (3) |
N13 | 0.0480 (10) | 0.0447 (10) | 0.0481 (10) | 0.0028 (8) | 0.0103 (8) | 0.0005 (8) |
C14 | 0.088 (3) | 0.064 (3) | 0.056 (2) | 0.010 (2) | 0.027 (2) | −0.003 (2) |
C15 | 0.079 (3) | 0.068 (3) | 0.060 (3) | 0.009 (2) | 0.027 (2) | 0.002 (2) |
N21 | 0.041 (2) | 0.119 (3) | 0.079 (3) | 0.004 (2) | 0.0136 (18) | 0.032 (2) |
C21 | 0.0398 (19) | 0.0417 (19) | 0.0435 (19) | −0.0026 (15) | 0.0108 (16) | −0.0045 (15) |
N22 | 0.0409 (16) | 0.0491 (17) | 0.0452 (17) | −0.0046 (13) | 0.0145 (14) | 0.0043 (13) |
C22 | 0.047 (2) | 0.083 (3) | 0.071 (3) | −0.020 (2) | 0.016 (2) | 0.001 (2) |
C23 | 0.080 (3) | 0.056 (2) | 0.053 (2) | 0.000 (2) | 0.029 (2) | 0.0093 (18) |
N23 | 0.0530 (19) | 0.0476 (17) | 0.0430 (17) | −0.0081 (14) | 0.0141 (14) | 0.0014 (13) |
C24 | 0.088 (3) | 0.057 (3) | 0.069 (3) | 0.015 (2) | 0.022 (2) | 0.016 (2) |
C25 | 0.083 (3) | 0.080 (3) | 0.060 (3) | −0.027 (2) | 0.034 (2) | 0.000 (2) |
N31 | 0.0399 (17) | 0.0632 (19) | 0.0425 (16) | −0.0012 (14) | 0.0123 (14) | −0.0007 (14) |
C31 | 0.0389 (19) | 0.0356 (18) | 0.0404 (19) | 0.0046 (14) | 0.0068 (15) | 0.0051 (14) |
N32 | 0.0491 (17) | 0.0466 (17) | 0.0378 (16) | −0.0035 (13) | 0.0091 (13) | 0.0034 (13) |
C32 | 0.071 (3) | 0.057 (2) | 0.054 (2) | −0.012 (2) | 0.003 (2) | −0.0072 (19) |
C33 | 0.068 (3) | 0.077 (3) | 0.045 (2) | 0.000 (2) | 0.015 (2) | 0.011 (2) |
N33 | 0.0382 (16) | 0.0564 (18) | 0.0418 (16) | −0.0016 (13) | 0.0101 (13) | 0.0071 (13) |
C34 | 0.036 (2) | 0.082 (3) | 0.069 (3) | 0.0007 (19) | 0.0138 (19) | 0.005 (2) |
C35 | 0.061 (3) | 0.080 (3) | 0.046 (2) | −0.007 (2) | 0.0171 (19) | 0.013 (2) |
Bi1—Cl1 | 2.5301 (9) | N22—C22 | 1.446 (4) |
Bi1—Cl4 | 2.5378 (9) | N22—C23 | 1.461 (4) |
Bi1—Cl7 | 2.6055 (9) | C22—H221 | 0.9600 |
Bi1—Cl8 | 2.8357 (9) | C22—H222 | 0.9600 |
Bi1—Cl5 | 2.9754 (8) | C22—H223 | 0.9600 |
Bi1—Cl2 | 3.0527 (9) | C23—H231 | 0.9600 |
Bi2—Cl3 | 2.5534 (9) | C23—H232 | 0.9600 |
Bi2—Cl9 | 2.5704 (9) | C23—H233 | 0.9600 |
Bi2—Cl6 | 2.6088 (8) | N23—C25 | 1.455 (4) |
Bi2—Cl5 | 2.8621 (8) | N23—C24 | 1.462 (5) |
Bi2—Cl8 | 2.8890 (9) | C24—H241 | 0.9600 |
Bi2—Cl2 | 2.9797 (9) | C24—H242 | 0.9600 |
N11—C11 | 1.322 (4) | C24—H243 | 0.9600 |
N11—H111 | 0.8600 | C25—H251 | 0.9600 |
N11—H112 | 0.8600 | C25—H252 | 0.9600 |
C11—N12 | 1.310 (4) | C25—H253 | 0.9600 |
C11—N13 | 1.329 (4) | N31—C31 | 1.320 (4) |
N12—C13 | 1.457 (5) | N31—H311 | 0.8600 |
N12—C12 | 1.512 (5) | N31—H312 | 0.8600 |
C12—H121 | 0.9600 | C31—N33 | 1.327 (4) |
C12—H122 | 0.9600 | C31—N32 | 1.339 (4) |
C12—H123 | 0.9600 | N32—C32 | 1.458 (4) |
C13—H131 | 0.9600 | N32—C33 | 1.461 (4) |
C13—H132 | 0.9600 | C32—H321 | 0.9600 |
C13—H133 | 0.9600 | C32—H322 | 0.9600 |
N13—C15 | 1.445 (4) | C32—H323 | 0.9600 |
N13—C14 | 1.464 (5) | C33—H331 | 0.9600 |
C14—H141 | 0.9600 | C33—H332 | 0.9600 |
C14—H142 | 0.9600 | C33—H333 | 0.9600 |
C14—H143 | 0.9600 | N33—C34 | 1.463 (4) |
C15—H151 | 0.9600 | N33—C35 | 1.467 (4) |
C15—H152 | 0.9600 | C34—H341 | 0.9600 |
C15—H153 | 0.9600 | C34—H342 | 0.9600 |
N21—C21 | 1.320 (4) | C34—H343 | 0.9600 |
N21—H211 | 0.8600 | C35—H351 | 0.9600 |
N21—H212 | 0.8600 | C35—H352 | 0.9600 |
C21—N23 | 1.322 (4) | C35—H353 | 0.9600 |
C21—N22 | 1.331 (4) | ||
Cl1—Bi1—Cl4 | 94.60 (3) | H211—N21—H212 | 120.0 |
Cl1—Bi1—Cl7 | 90.67 (3) | N21—C21—N23 | 119.0 (3) |
Cl4—Bi1—Cl7 | 91.47 (3) | N21—C21—N22 | 119.3 (3) |
Cl1—Bi1—Cl8 | 91.08 (3) | N23—C21—N22 | 121.7 (3) |
Cl4—Bi1—Cl8 | 93.67 (3) | C21—N22—C22 | 121.7 (3) |
Cl7—Bi1—Cl8 | 174.42 (3) | C21—N22—C23 | 120.5 (3) |
Cl1—Bi1—Cl5 | 89.59 (3) | C22—N22—C23 | 115.6 (3) |
Cl4—Bi1—Cl5 | 173.61 (3) | N22—C22—H221 | 109.5 |
Cl7—Bi1—Cl5 | 93.31 (3) | N22—C22—H222 | 109.5 |
Cl8—Bi1—Cl5 | 81.41 (2) | H221—C22—H222 | 109.5 |
Cl1—Bi1—Cl2 | 164.13 (3) | N22—C22—H223 | 109.5 |
Cl4—Bi1—Cl2 | 97.29 (3) | H221—C22—H223 | 109.5 |
Cl7—Bi1—Cl2 | 99.48 (3) | H222—C22—H223 | 109.5 |
Cl8—Bi1—Cl2 | 77.73 (3) | N22—C23—H231 | 109.5 |
Cl5—Bi1—Cl2 | 77.74 (2) | N22—C23—H232 | 109.5 |
Cl3—Bi2—Cl9 | 95.12 (3) | H231—C23—H232 | 109.5 |
Cl3—Bi2—Cl6 | 89.63 (3) | N22—C23—H233 | 109.5 |
Cl9—Bi2—Cl6 | 90.67 (3) | H231—C23—H233 | 109.5 |
Cl3—Bi2—Cl5 | 94.62 (3) | H232—C23—H233 | 109.5 |
Cl9—Bi2—Cl5 | 94.98 (3) | C21—N23—C25 | 122.3 (3) |
Cl6—Bi2—Cl5 | 172.59 (3) | C21—N23—C24 | 121.8 (3) |
Cl3—Bi2—Cl8 | 94.62 (3) | C25—N23—C24 | 114.8 (3) |
Cl9—Bi2—Cl8 | 170.11 (3) | N23—C24—H241 | 109.5 |
Cl6—Bi2—Cl8 | 91.14 (3) | N23—C24—H242 | 109.5 |
Cl5—Bi2—Cl8 | 82.48 (2) | H241—C24—H242 | 109.5 |
Cl3—Bi2—Cl2 | 171.77 (3) | N23—C24—H243 | 109.5 |
Cl9—Bi2—Cl2 | 92.05 (3) | H241—C24—H243 | 109.5 |
Cl6—Bi2—Cl2 | 94.33 (3) | H242—C24—H243 | 109.5 |
Cl5—Bi2—Cl2 | 80.70 (2) | N23—C25—H251 | 109.5 |
Cl8—Bi2—Cl2 | 78.12 (3) | N23—C25—H252 | 109.5 |
Bi2—Cl2—Bi1 | 81.51 (2) | H251—C25—H252 | 109.5 |
Bi2—Cl5—Bi1 | 84.84 (2) | N23—C25—H253 | 109.5 |
Bi1—Cl8—Bi2 | 86.94 (2) | H251—C25—H253 | 109.5 |
C11—N11—H111 | 120.0 | H252—C25—H253 | 109.5 |
C11—N11—H112 | 120.0 | C31—N31—H311 | 120.0 |
H111—N11—H112 | 120.0 | C31—N31—H312 | 120.0 |
N12—C11—N11 | 118.1 (4) | H311—N31—H312 | 120.0 |
N12—C11—N13 | 121.1 (3) | N31—C31—N33 | 119.9 (3) |
N11—C11—N13 | 120.9 (3) | N31—C31—N32 | 119.4 (3) |
C11—N12—C13 | 121.7 (4) | N33—C31—N32 | 120.7 (3) |
C11—N12—C12 | 121.0 (3) | C31—N32—C32 | 121.4 (3) |
C13—N12—C12 | 116.1 (3) | C31—N32—C33 | 120.7 (3) |
N12—C12—H121 | 109.5 | C32—N32—C33 | 115.6 (3) |
N12—C12—H122 | 109.5 | N32—C32—H321 | 109.5 |
H121—C12—H122 | 109.5 | N32—C32—H322 | 109.5 |
N12—C12—H123 | 109.5 | H321—C32—H322 | 109.5 |
H121—C12—H123 | 109.5 | N32—C32—H323 | 109.5 |
H122—C12—H123 | 109.5 | H321—C32—H323 | 109.5 |
N12—C13—H131 | 109.5 | H322—C32—H323 | 109.5 |
N12—C13—H132 | 109.5 | N32—C33—H331 | 109.5 |
H131—C13—H132 | 109.5 | N32—C33—H332 | 109.5 |
N12—C13—H133 | 109.5 | H331—C33—H332 | 109.5 |
H131—C13—H133 | 109.5 | N32—C33—H333 | 109.5 |
H132—C13—H133 | 109.5 | H331—C33—H333 | 109.5 |
C11—N13—C15 | 119.4 (3) | H332—C33—H333 | 109.5 |
C11—N13—C14 | 124.9 (3) | C31—N33—C34 | 122.3 (3) |
C15—N13—C14 | 114.9 (3) | C31—N33—C35 | 120.8 (3) |
N13—C14—H141 | 109.5 | C34—N33—C35 | 114.9 (3) |
N13—C14—H142 | 109.5 | N33—C34—H341 | 109.5 |
H141—C14—H142 | 109.5 | N33—C34—H342 | 109.5 |
N13—C14—H143 | 109.5 | H341—C34—H342 | 109.5 |
H141—C14—H143 | 109.5 | N33—C34—H343 | 109.5 |
H142—C14—H143 | 109.5 | H341—C34—H343 | 109.5 |
N13—C15—H151 | 109.5 | H342—C34—H343 | 109.5 |
N13—C15—H152 | 109.5 | N33—C35—H351 | 109.5 |
H151—C15—H152 | 109.5 | N33—C35—H352 | 109.5 |
N13—C15—H153 | 109.5 | H351—C35—H352 | 109.5 |
H151—C15—H153 | 109.5 | N33—C35—H353 | 109.5 |
H152—C15—H153 | 109.5 | H351—C35—H353 | 109.5 |
C21—N21—H211 | 120.0 | H352—C35—H353 | 109.5 |
C21—N21—H212 | 120.0 | ||
N11—C11—N12—C13 | −17.9 (6) | N21—C21—N23—C25 | −14.4 (5) |
N13—C11—N12—C13 | 162.2 (4) | N22—C21—N23—C25 | 166.7 (3) |
N11—C11—N12—C12 | 149.2 (4) | N21—C21—N23—C24 | 152.8 (4) |
N13—C11—N12—C12 | −30.7 (5) | N22—C21—N23—C24 | −26.1 (5) |
N12—C11—N13—C15 | 159.9 (3) | N31—C31—N32—C32 | −144.2 (3) |
N11—C11—N13—C15 | −19.9 (5) | N33—C31—N32—C32 | 36.4 (5) |
N12—C11—N13—C14 | −31.0 (6) | N31—C31—N32—C33 | 17.5 (5) |
N11—C11—N13—C14 | 149.2 (4) | N33—C31—N32—C33 | −161.9 (3) |
N21—C21—N22—C22 | 140.5 (4) | N31—C31—N33—C34 | −144.1 (3) |
N23—C21—N22—C22 | −40.5 (5) | N32—C31—N33—C34 | 35.3 (5) |
N21—C21—N22—C23 | −22.3 (5) | N31—C31—N33—C35 | 19.3 (5) |
N23—C21—N22—C23 | 156.6 (3) | N32—C31—N33—C35 | −161.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H111···Cl2 | 0.86 | 2.63 | 3.304 (3) | 136 |
N11—H112···Cl6 | 0.86 | 2.44 | 3.242 (3) | 155 |
N21—H212···Cl2 | 0.86 | 2.83 | 3.522 (4) | 138 |
N21—H211···Cl6 | 0.86 | 2.84 | 3.376 (4) | 122 |
N21—H211···Cl9 | 0.86 | 2.79 | 3.443 (3) | 134 |
N31—H311···Cl5 | 0.86 | 2.74 | 3.416 (3) | 137 |
N31—H312···Cl7i | 0.86 | 2.70 | 3.411 (3) | 141 |
C23—H232···Cl5ii | 0.96 | 2.82 | 3.702 (4) | 153 |
C23—H233···Cl7iii | 0.96 | 2.71 | 3.582 (4) | 151 |
C12—H121···N13 | 0.96 | 2.51 | 2.854 (5) | 101 |
C14—H141···N12 | 0.96 | 2.59 | 2.911 (5) | 100 |
C22—H221···N23 | 0.96 | 2.57 | 2.905 (5) | 101 |
C24—H241···N22 | 0.96 | 2.48 | 2.845 (5) | 102 |
C32—H321···N33 | 0.96 | 2.52 | 2.875 (5) | 102 |
C34—H341···N32 | 0.96 | 2.55 | 2.886 (5) | 100 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x+1, y, z; (iii) −x+1, −y+1, −z+1. |
(C5H14N3)[BiCl4] | Z = 4 |
Mr = 466.97 | F(000) = 864 |
Triclinic, P1 | Dx = 2.273 Mg m−3 |
a = 7.7179 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.5660 (5) Å | Cell parameters from 5942 reflections |
c = 18.0362 (7) Å | θ = 3.2–29.3° |
α = 95.585 (3)° | µ = 13.67 mm−1 |
β = 91.008 (3)° | T = 295 K |
γ = 110.965 (4)° | Pillar, colourless |
V = 1364.74 (11) Å3 | 0.31 × 0.22 × 0.06 mm |
Xcalibur diffractometer | 4631 reflections with I > 2σ(I) |
ω–scan | Rint = 0.030 |
Absorption correction: analytical CrysAlisPro 1.171.40.56a (Rigaku Oxford Diffraction, 2019) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | θmax = 26.0°, θmin = 3.0° |
Tmin = 0.09, Tmax = 0.49 | h = −9→6 |
9281 measured reflections | k = −13→13 |
5286 independent reflections | l = −22→22 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.026 | H-atom parameters constrained |
wR(F2) = 0.059 | w = 1/[σ2(Fo2) + (0.0208P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
5286 reflections | Δρmax = 0.69 e Å−3 |
244 parameters | Δρmin = −0.76 e Å−3 |
0 restraints | Extinction correction: SHELXL-2014/7 (Sheldrick 2014, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00533 (17) |
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 | ||
Bi1 | −0.03098 (2) | 0.21386 (2) | 0.31887 (2) | 0.03733 (7) | |
Cl1 | −0.0051 (2) | 0.05740 (15) | 0.40971 (9) | 0.0644 (4) | |
Cl2 | −0.16017 (18) | 0.38086 (15) | 0.21434 (9) | 0.0623 (4) | |
Cl3 | −0.0778 (2) | 0.37333 (17) | 0.42162 (9) | 0.0700 (4) | |
Cl4 | 0.10690 (19) | 0.06298 (16) | 0.19700 (10) | 0.0691 (5) | |
Cl5 | 0.33920 (18) | 0.35196 (14) | 0.34011 (9) | 0.0565 (4) | |
Cl6 | −0.4051 (2) | 0.06421 (18) | 0.30445 (12) | 0.0830 (6) | |
Bi2 | 0.47181 (2) | 0.22420 (2) | 0.20850 (2) | 0.03656 (7) | |
Cl7 | 0.5155 (2) | 0.08178 (16) | 0.09500 (9) | 0.0664 (4) | |
Cl8 | 0.4005 (2) | 0.39216 (15) | 0.13139 (10) | 0.0666 (4) | |
N11 | 0.5139 (7) | 0.7670 (6) | 0.5078 (3) | 0.0822 (18) | |
H111 | 0.4380 | 0.7970 | 0.5314 | 0.099* | |
H112 | 0.6012 | 0.7532 | 0.5321 | 0.099* | |
C11 | 0.4963 (7) | 0.7422 (5) | 0.4339 (3) | 0.0498 (13) | |
N12 | 0.6132 (6) | 0.6947 (4) | 0.3984 (3) | 0.0499 (11) | |
C12 | 0.6680 (9) | 0.7244 (7) | 0.3235 (4) | 0.080 (2) | |
H121 | 0.6130 | 0.7858 | 0.3069 | 0.120* | |
H122 | 0.6262 | 0.6412 | 0.2903 | 0.120* | |
H123 | 0.8009 | 0.7657 | 0.3238 | 0.120* | |
C13 | 0.7216 (8) | 0.6319 (7) | 0.4384 (4) | 0.075 (2) | |
H131 | 0.8387 | 0.7002 | 0.4566 | 0.112* | |
H132 | 0.7430 | 0.5629 | 0.4052 | 0.112* | |
H133 | 0.6546 | 0.5913 | 0.4796 | 0.112* | |
N13 | 0.3615 (6) | 0.7641 (5) | 0.3976 (3) | 0.0556 (12) | |
C14 | 0.2655 (10) | 0.6826 (7) | 0.3302 (4) | 0.088 (2) | |
H141 | 0.3165 | 0.6136 | 0.3165 | 0.132* | |
H142 | 0.2802 | 0.7399 | 0.2907 | 0.132* | |
H143 | 0.1358 | 0.6402 | 0.3383 | 0.132* | |
C15 | 0.2735 (9) | 0.8558 (8) | 0.4307 (4) | 0.082 (2) | |
H151 | 0.3587 | 0.9222 | 0.4671 | 0.123* | |
H152 | 0.1640 | 0.8042 | 0.4543 | 0.123* | |
H153 | 0.2400 | 0.9012 | 0.3924 | 0.123* | |
N21 | 0.0315 (7) | 0.7625 (6) | −0.0444 (3) | 0.0752 (17) | |
H211 | 0.1136 | 0.7457 | −0.0711 | 0.090* | |
H212 | −0.0462 | 0.7928 | −0.0640 | 0.090* | |
C21 | 0.0247 (7) | 0.7417 (5) | 0.0272 (3) | 0.0486 (13) | |
N22 | 0.1447 (6) | 0.6952 (5) | 0.0565 (3) | 0.0518 (11) | |
C22 | 0.2214 (10) | 0.7360 (7) | 0.1328 (4) | 0.083 (2) | |
H221 | 0.1660 | 0.7957 | 0.1573 | 0.125* | |
H222 | 0.3534 | 0.7828 | 0.1328 | 0.125* | |
H223 | 0.1956 | 0.6566 | 0.1587 | 0.125* | |
C23 | 0.2413 (8) | 0.6230 (6) | 0.0084 (4) | 0.0693 (18) | |
H231 | 0.1627 | 0.5762 | −0.0351 | 0.104* | |
H232 | 0.2690 | 0.5582 | 0.0356 | 0.104* | |
H233 | 0.3547 | 0.6878 | −0.0064 | 0.104* | |
N23 | −0.1047 (6) | 0.7679 (5) | 0.0671 (3) | 0.0569 (12) | |
C24 | −0.1815 (11) | 0.6964 (7) | 0.1312 (4) | 0.092 (2) | |
H241 | −0.1291 | 0.6279 | 0.1371 | 0.139* | |
H242 | −0.3141 | 0.6540 | 0.1233 | 0.139* | |
H243 | −0.1520 | 0.7603 | 0.1754 | 0.139* | |
C25 | −0.2012 (8) | 0.8532 (8) | 0.0420 (5) | 0.083 (2) | |
H251 | −0.1230 | 0.9164 | 0.0109 | 0.124* | |
H252 | −0.2303 | 0.9025 | 0.0844 | 0.124* | |
H253 | −0.3140 | 0.7968 | 0.0140 | 0.124* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Bi1 | 0.03750 (11) | 0.04648 (12) | 0.03575 (12) | 0.02369 (9) | 0.00246 (8) | 0.00779 (8) |
Cl1 | 0.0806 (10) | 0.0680 (9) | 0.0623 (10) | 0.0437 (8) | 0.0002 (8) | 0.0250 (8) |
Cl2 | 0.0445 (7) | 0.0640 (9) | 0.0737 (11) | 0.0077 (7) | −0.0059 (7) | 0.0337 (8) |
Cl3 | 0.0968 (12) | 0.0769 (10) | 0.0585 (10) | 0.0591 (9) | 0.0153 (9) | 0.0013 (8) |
Cl4 | 0.0445 (7) | 0.0649 (9) | 0.0800 (12) | 0.0073 (7) | 0.0055 (7) | −0.0286 (8) |
Cl5 | 0.0485 (7) | 0.0573 (8) | 0.0557 (9) | 0.0145 (6) | −0.0020 (6) | −0.0134 (7) |
Cl6 | 0.0474 (8) | 0.0795 (11) | 0.1264 (17) | 0.0150 (8) | 0.0001 (9) | 0.0632 (11) |
Bi2 | 0.03232 (11) | 0.04369 (12) | 0.03724 (12) | 0.01759 (8) | 0.00117 (8) | 0.00645 (8) |
Cl7 | 0.0768 (10) | 0.0673 (9) | 0.0596 (10) | 0.0331 (8) | 0.0202 (8) | −0.0017 (8) |
Cl8 | 0.0656 (9) | 0.0618 (9) | 0.0790 (11) | 0.0280 (7) | −0.0140 (8) | 0.0234 (8) |
N11 | 0.081 (4) | 0.140 (5) | 0.053 (4) | 0.073 (4) | 0.005 (3) | 0.010 (3) |
C11 | 0.041 (3) | 0.054 (3) | 0.054 (4) | 0.015 (2) | 0.003 (3) | 0.017 (3) |
N12 | 0.045 (2) | 0.048 (2) | 0.058 (3) | 0.020 (2) | 0.000 (2) | 0.002 (2) |
C12 | 0.095 (5) | 0.080 (5) | 0.066 (5) | 0.033 (4) | 0.030 (4) | 0.003 (4) |
C13 | 0.058 (4) | 0.081 (5) | 0.095 (6) | 0.038 (4) | −0.009 (4) | 0.000 (4) |
N13 | 0.051 (3) | 0.057 (3) | 0.064 (3) | 0.023 (2) | −0.002 (2) | 0.021 (2) |
C14 | 0.088 (5) | 0.077 (5) | 0.094 (6) | 0.026 (4) | −0.044 (4) | 0.007 (4) |
C15 | 0.063 (4) | 0.100 (5) | 0.101 (6) | 0.047 (4) | 0.013 (4) | 0.023 (5) |
N21 | 0.061 (3) | 0.134 (5) | 0.054 (3) | 0.057 (3) | 0.013 (3) | 0.037 (3) |
C21 | 0.040 (3) | 0.051 (3) | 0.047 (3) | 0.007 (2) | 0.001 (2) | 0.004 (3) |
N22 | 0.052 (3) | 0.057 (3) | 0.047 (3) | 0.018 (2) | 0.000 (2) | 0.012 (2) |
C22 | 0.107 (6) | 0.079 (5) | 0.062 (5) | 0.033 (4) | −0.027 (4) | 0.006 (4) |
C23 | 0.067 (4) | 0.068 (4) | 0.081 (5) | 0.032 (3) | 0.004 (3) | 0.016 (4) |
N23 | 0.052 (3) | 0.056 (3) | 0.057 (3) | 0.014 (2) | 0.009 (2) | −0.001 (2) |
C24 | 0.115 (6) | 0.066 (4) | 0.084 (6) | 0.015 (4) | 0.053 (5) | 0.014 (4) |
C25 | 0.046 (4) | 0.094 (5) | 0.113 (7) | 0.031 (4) | 0.002 (4) | 0.007 (5) |
Bi1—Cl1 | 2.4917 (13) | N13—C15 | 1.458 (8) |
Bi1—Cl3 | 2.5011 (15) | C14—H141 | 0.9600 |
Bi1—Cl5 | 2.7033 (13) | C14—H142 | 0.9600 |
Bi1—Cl6 | 2.7441 (15) | C14—H143 | 0.9600 |
Bi1—Cl4 | 3.0199 (15) | C15—H151 | 0.9600 |
Bi1—Cl2 | 3.0826 (14) | C15—H152 | 0.9600 |
Cl2—Bi2i | 2.7220 (13) | C15—H153 | 0.9600 |
Cl4—Bi2 | 2.7119 (14) | N21—C21 | 1.330 (7) |
Cl5—Bi2 | 2.9925 (14) | N21—H211 | 0.8600 |
Cl6—Bi2i | 2.9011 (15) | N21—H212 | 0.8600 |
Bi2—Cl7 | 2.5212 (15) | C21—N22 | 1.318 (7) |
Bi2—Cl8 | 2.5572 (14) | C21—N23 | 1.333 (7) |
Bi2—Cl2ii | 2.7220 (13) | N22—C22 | 1.450 (8) |
Bi2—Cl6ii | 2.9010 (15) | N22—C23 | 1.479 (7) |
N11—C11 | 1.329 (7) | C22—H221 | 0.9600 |
N11—H111 | 0.8600 | C22—H222 | 0.9600 |
N11—H112 | 0.8600 | C22—H223 | 0.9600 |
C11—N13 | 1.319 (6) | C23—H231 | 0.9600 |
C11—N12 | 1.326 (7) | C23—H232 | 0.9600 |
N12—C12 | 1.453 (8) | C23—H233 | 0.9600 |
N12—C13 | 1.460 (7) | N23—C25 | 1.456 (8) |
C12—H121 | 0.9600 | N23—C24 | 1.461 (8) |
C12—H122 | 0.9600 | C24—H241 | 0.9600 |
C12—H123 | 0.9600 | C24—H242 | 0.9600 |
C13—H131 | 0.9600 | C24—H243 | 0.9600 |
C13—H132 | 0.9600 | C25—H251 | 0.9600 |
C13—H133 | 0.9600 | C25—H252 | 0.9600 |
N13—C14 | 1.442 (8) | C25—H253 | 0.9600 |
Cl1—Bi1—Cl3 | 91.12 (5) | H131—C13—H133 | 109.5 |
Cl1—Bi1—Cl5 | 89.01 (5) | H132—C13—H133 | 109.5 |
Cl3—Bi1—Cl5 | 88.43 (5) | C11—N13—C14 | 123.5 (5) |
Cl1—Bi1—Cl6 | 87.39 (5) | C11—N13—C15 | 121.6 (6) |
Cl3—Bi1—Cl6 | 91.22 (6) | C14—N13—C15 | 113.9 (5) |
Cl5—Bi1—Cl6 | 176.37 (5) | N13—C14—H141 | 109.5 |
Cl1—Bi1—Cl4 | 91.01 (5) | N13—C14—H142 | 109.5 |
Cl3—Bi1—Cl4 | 168.17 (5) | H141—C14—H142 | 109.5 |
Cl5—Bi1—Cl4 | 79.98 (4) | N13—C14—H143 | 109.5 |
Cl6—Bi1—Cl4 | 100.50 (6) | H141—C14—H143 | 109.5 |
Cl1—Bi1—Cl2 | 166.53 (5) | H142—C14—H143 | 109.5 |
Cl3—Bi1—Cl2 | 84.94 (5) | N13—C15—H151 | 109.5 |
Cl5—Bi1—Cl2 | 103.72 (4) | N13—C15—H152 | 109.5 |
Cl6—Bi1—Cl2 | 79.84 (4) | H151—C15—H152 | 109.5 |
Cl4—Bi1—Cl2 | 95.48 (5) | N13—C15—H153 | 109.5 |
Bi2i—Cl2—Bi1 | 96.37 (4) | H151—C15—H153 | 109.5 |
Bi2—Cl4—Bi1 | 99.03 (4) | H152—C15—H153 | 109.5 |
Bi1—Cl5—Bi2 | 99.90 (4) | C21—N21—H211 | 120.0 |
Bi1—Cl6—Bi2i | 100.22 (5) | C21—N21—H212 | 120.0 |
Cl7—Bi2—Cl8 | 93.38 (6) | H211—N21—H212 | 120.0 |
Cl7—Bi2—Cl4 | 87.84 (5) | N22—C21—N21 | 119.3 (5) |
Cl8—Bi2—Cl4 | 89.98 (5) | N22—C21—N23 | 122.0 (5) |
Cl7—Bi2—Cl2ii | 89.77 (5) | N21—C21—N23 | 118.7 (5) |
Cl8—Bi2—Cl2ii | 89.78 (5) | C21—N22—C22 | 122.9 (5) |
Cl4—Bi2—Cl2ii | 177.58 (5) | C21—N22—C23 | 120.7 (5) |
Cl7—Bi2—Cl6ii | 90.17 (6) | C22—N22—C23 | 115.0 (5) |
Cl8—Bi2—Cl6ii | 172.42 (5) | N22—C22—H221 | 109.5 |
Cl4—Bi2—Cl6ii | 96.85 (5) | N22—C22—H222 | 109.5 |
Cl2ii—Bi2—Cl6ii | 83.54 (4) | H221—C22—H222 | 109.5 |
Cl7—Bi2—Cl5 | 168.16 (5) | N22—C22—H223 | 109.5 |
Cl8—Bi2—Cl5 | 87.43 (5) | H221—C22—H223 | 109.5 |
Cl4—Bi2—Cl5 | 80.34 (4) | H222—C22—H223 | 109.5 |
Cl2ii—Bi2—Cl5 | 102.06 (5) | N22—C23—H231 | 109.5 |
Cl6ii—Bi2—Cl5 | 90.46 (6) | N22—C23—H232 | 109.5 |
C11—N11—H111 | 120.0 | H231—C23—H232 | 109.5 |
C11—N11—H112 | 120.0 | N22—C23—H233 | 109.5 |
H111—N11—H112 | 120.0 | H231—C23—H233 | 109.5 |
N13—C11—N12 | 121.6 (6) | H232—C23—H233 | 109.5 |
N13—C11—N11 | 119.1 (5) | C21—N23—C25 | 121.5 (5) |
N12—C11—N11 | 119.2 (5) | C21—N23—C24 | 122.8 (5) |
C11—N12—C12 | 122.8 (5) | C25—N23—C24 | 115.0 (5) |
C11—N12—C13 | 120.5 (5) | N23—C24—H241 | 109.5 |
C12—N12—C13 | 115.6 (5) | N23—C24—H242 | 109.5 |
N12—C12—H121 | 109.5 | H241—C24—H242 | 109.5 |
N12—C12—H122 | 109.5 | N23—C24—H243 | 109.5 |
H121—C12—H122 | 109.5 | H241—C24—H243 | 109.5 |
N12—C12—H123 | 109.5 | H242—C24—H243 | 109.5 |
H121—C12—H123 | 109.5 | N23—C25—H251 | 109.5 |
H122—C12—H123 | 109.5 | N23—C25—H252 | 109.5 |
N12—C13—H131 | 109.5 | H251—C25—H252 | 109.5 |
N12—C13—H132 | 109.5 | N23—C25—H253 | 109.5 |
H131—C13—H132 | 109.5 | H251—C25—H253 | 109.5 |
N12—C13—H133 | 109.5 | H252—C25—H253 | 109.5 |
N13—C11—N12—C12 | 31.3 (8) | N21—C21—N22—C22 | 145.0 (6) |
N11—C11—N12—C12 | −149.4 (6) | N23—C21—N22—C22 | −35.5 (8) |
N13—C11—N12—C13 | −160.9 (5) | N21—C21—N22—C23 | −20.9 (8) |
N11—C11—N12—C13 | 18.4 (8) | N23—C21—N22—C23 | 158.7 (5) |
N12—C11—N13—C14 | 33.1 (8) | N22—C21—N23—C25 | 162.6 (5) |
N11—C11—N13—C14 | −146.2 (7) | N21—C21—N23—C25 | −17.9 (8) |
N12—C11—N13—C15 | −159.3 (5) | N22—C21—N23—C24 | −28.0 (8) |
N11—C11—N13—C15 | 21.4 (8) | N21—C21—N23—C24 | 151.5 (6) |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H112···Cl5iii | 0.86 | 2.75 | 3.460 (6) | 140 |
C12—H121···N13 | 0.96 | 2.52 | 2.876 (8) | 102 |
C14—H141···N12 | 0.96 | 2.53 | 2.888 (8) | 102 |
C22—H221···N23 | 0.96 | 2.54 | 2.903 (8) | 103 |
C24—H241···N22 | 0.96 | 2.51 | 2.881 (9) | 103 |
Symmetry code: (iii) −x+1, −y+1, −z+1. |
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