Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229620006130/fp3085sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620006130/fp30851sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620006130/fp30852sup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620006130/fp30853sup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620006130/fp30854sup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620006130/fp30855sup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620006130/fp30856sup7.hkl |
CCDC references: 2001365; 2001364; 2001363; 2001362; 2001361; 2001360
For all structures, data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2020); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b) and PLATON (Spek, 2015, 2020).
(C5H9N3)2[BiCl6]Cl·H2O | Z = 2 |
Mr = 697.45 | F(000) = 664 |
Triclinic, P1 | Dx = 2.135 Mg m−3 |
a = 9.1612 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.8591 (6) Å | Cell parameters from 5333 reflections |
c = 11.7273 (7) Å | θ = 3.5–29.2° |
α = 94.303 (4)° | µ = 9.00 mm−1 |
β = 101.914 (4)° | T = 160 K |
γ = 106.254 (4)° | Prism, red |
V = 1084.89 (10) Å3 | 0.25 × 0.20 × 0.10 mm |
Oxford Diffraction SuperNova dual radiation diffractometer | 5056 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray source | 4589 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.040 |
Detector resolution: 10.3801 pixels mm-1 | θmax = 29.4°, θmin = 2.9° |
ω scans | h = −11→9 |
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2018) | k = −14→14 |
Tmin = 0.551, Tmax = 1.000 | l = −16→13 |
8459 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: geom & difmap |
R[F2 > 2σ(F2)] = 0.036 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.075 | w = 1/[σ2(Fo2) + (0.0172P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.002 |
5054 reflections | Δρmax = 3.53 e Å−3 |
237 parameters | Δρmin = −1.74 e Å−3 |
2 restraints | Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: dual | Extinction coefficient: 0.00175 (19) |
Experimental. Data collection and full structure determination done by Prof. Anthony Linden: anthony.linden@chem.uzh.ch Solvent used: 2M HCl Cooling Device: Oxford Instruments Cryojet XL Crystal mount: on a glass fibre Frames collected: 272 Seconds exposure per frame: 1.5 Degrees rotation per frame: 1.0 Crystal-detector distance (mm): 55.0 Client: Levi Senior Sample code: LS009 |
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. |
Refinement. The water H-atoms were refined isotropically with O-H distance restraints of 0.84 (1) Å. All other H atoms were placed in calculated positions and allowed to ride on their parent atoms. |
x | y | z | Uiso*/Ueq | ||
Bi1 | 0.33379 (2) | 0.65001 (2) | 0.77021 (2) | 0.01333 (8) | |
Cl1 | 0.30114 (15) | 0.87093 (12) | 0.86367 (13) | 0.0217 (3) | |
Cl2 | 0.62022 (15) | 0.67918 (13) | 0.92734 (13) | 0.0205 (3) | |
Cl3 | 0.13301 (14) | 0.50002 (12) | 0.90309 (12) | 0.0197 (3) | |
Cl4 | 0.35744 (16) | 0.43435 (12) | 0.65545 (13) | 0.0234 (3) | |
Cl5 | 0.06380 (14) | 0.62274 (12) | 0.62347 (12) | 0.0165 (3) | |
Cl6 | 0.47286 (14) | 0.77900 (12) | 0.62570 (13) | 0.0190 (3) | |
Cl7 | 1.20723 (15) | 0.98098 (13) | 0.50220 (13) | 0.0216 (3) | |
O1 | 0.7385 (4) | 0.6577 (4) | 0.6206 (4) | 0.0200 (8) | |
H11 | 0.714 (7) | 0.619 (5) | 0.552 (2) | 0.033 (19)* | |
H12 | 0.666 (5) | 0.687 (6) | 0.630 (6) | 0.039 (19)* | |
N1 | 1.0249 (5) | 1.1946 (4) | 0.8540 (4) | 0.0219 (11) | |
H1 | 1.077768 | 1.277490 | 0.863992 | 0.026* | |
N2 | 1.1604 (5) | 1.1615 (4) | 0.7142 (4) | 0.0239 (11) | |
H21 | 1.210656 | 1.245035 | 0.725912 | 0.029* | |
H22 | 1.180074 | 1.109362 | 0.662307 | 0.029* | |
N3 | 0.9957 (5) | 0.8895 (4) | 0.6795 (4) | 0.0207 (11) | |
H31 | 1.013412 | 0.926401 | 0.614533 | 0.031* | |
H32 | 0.910623 | 0.817732 | 0.658148 | 0.031* | |
H33 | 1.080894 | 0.866756 | 0.714239 | 0.031* | |
C1 | 1.0544 (6) | 1.1142 (5) | 0.7748 (5) | 0.0163 (11) | |
C2 | 0.9672 (6) | 0.9818 (5) | 0.7621 (5) | 0.0138 (10) | |
C3 | 0.8594 (6) | 0.9399 (5) | 0.8260 (5) | 0.0166 (11) | |
H3 | 0.801713 | 0.850647 | 0.816354 | 0.020* | |
C4 | 0.8338 (7) | 1.0302 (5) | 0.9070 (5) | 0.0237 (13) | |
H41 | 0.758216 | 1.002400 | 0.951731 | 0.028* | |
C5 | 0.9173 (6) | 1.1551 (5) | 0.9200 (5) | 0.0227 (13) | |
H5 | 0.902074 | 1.216442 | 0.974894 | 0.027* | |
N4 | 0.6479 (5) | 0.1627 (4) | 0.6711 (4) | 0.0182 (10) | |
H4 | 0.660330 | 0.111762 | 0.614219 | 0.022* | |
N5 | 0.8359 (5) | 0.3288 (4) | 0.6238 (4) | 0.0236 (11) | |
H51 | 0.847672 | 0.273505 | 0.570243 | 0.028* | |
H52 | 0.892155 | 0.410810 | 0.634629 | 0.028* | |
N6 | 0.7879 (5) | 0.5058 (4) | 0.7981 (4) | 0.0163 (10) | |
H61 | 0.764422 | 0.540181 | 0.730778 | 0.024* | |
H62 | 0.892872 | 0.518114 | 0.819174 | 0.024* | |
H63 | 0.758381 | 0.545460 | 0.856654 | 0.024* | |
C6 | 0.7327 (6) | 0.2881 (5) | 0.6888 (5) | 0.0147 (11) | |
C7 | 0.7050 (6) | 0.3677 (5) | 0.7784 (5) | 0.0139 (10) | |
C8 | 0.6028 (5) | 0.3158 (5) | 0.8446 (5) | 0.0163 (11) | |
H8 | 0.585925 | 0.369955 | 0.904868 | 0.020* | |
C9 | 0.5238 (6) | 0.1843 (5) | 0.8239 (5) | 0.0205 (12) | |
H9 | 0.455741 | 0.147067 | 0.871621 | 0.025* | |
C10 | 0.5452 (6) | 0.1091 (5) | 0.7341 (5) | 0.0191 (12) | |
H10 | 0.488022 | 0.019523 | 0.716078 | 0.023* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Bi1 | 0.01174 (11) | 0.01138 (11) | 0.01661 (13) | 0.00237 (7) | 0.00483 (8) | 0.00072 (8) |
Cl1 | 0.0263 (7) | 0.0161 (7) | 0.0216 (8) | 0.0048 (5) | 0.0082 (6) | −0.0046 (6) |
Cl2 | 0.0183 (6) | 0.0211 (7) | 0.0211 (8) | 0.0060 (5) | 0.0035 (6) | 0.0002 (6) |
Cl3 | 0.0194 (6) | 0.0190 (7) | 0.0191 (8) | 0.0026 (5) | 0.0055 (6) | 0.0032 (6) |
Cl4 | 0.0300 (7) | 0.0165 (7) | 0.0251 (8) | 0.0083 (5) | 0.0090 (6) | −0.0004 (6) |
Cl5 | 0.0154 (6) | 0.0157 (6) | 0.0166 (7) | 0.0032 (5) | 0.0028 (5) | −0.0004 (5) |
Cl6 | 0.0194 (6) | 0.0180 (7) | 0.0231 (8) | 0.0070 (5) | 0.0096 (6) | 0.0057 (6) |
Cl7 | 0.0239 (7) | 0.0247 (7) | 0.0199 (8) | 0.0109 (5) | 0.0088 (6) | 0.0025 (6) |
O1 | 0.0153 (19) | 0.024 (2) | 0.022 (3) | 0.0085 (16) | 0.0050 (18) | −0.0008 (19) |
N1 | 0.023 (2) | 0.012 (2) | 0.030 (3) | 0.0060 (18) | 0.004 (2) | 0.002 (2) |
N2 | 0.028 (3) | 0.011 (2) | 0.030 (3) | −0.0012 (19) | 0.014 (2) | −0.004 (2) |
N3 | 0.027 (3) | 0.010 (2) | 0.026 (3) | 0.0038 (18) | 0.013 (2) | 0.002 (2) |
C1 | 0.014 (2) | 0.016 (3) | 0.021 (3) | 0.006 (2) | 0.004 (2) | 0.004 (2) |
C2 | 0.016 (2) | 0.015 (3) | 0.011 (3) | 0.007 (2) | 0.001 (2) | 0.001 (2) |
C3 | 0.015 (2) | 0.019 (3) | 0.013 (3) | 0.002 (2) | 0.002 (2) | 0.000 (2) |
C4 | 0.022 (3) | 0.030 (3) | 0.023 (4) | 0.011 (2) | 0.012 (3) | 0.005 (3) |
C5 | 0.023 (3) | 0.031 (3) | 0.017 (3) | 0.013 (2) | 0.006 (3) | −0.001 (3) |
N4 | 0.019 (2) | 0.015 (2) | 0.017 (3) | 0.0016 (18) | 0.004 (2) | −0.003 (2) |
N5 | 0.030 (3) | 0.018 (2) | 0.025 (3) | 0.0024 (19) | 0.016 (2) | 0.001 (2) |
N6 | 0.016 (2) | 0.013 (2) | 0.019 (3) | 0.0041 (17) | 0.005 (2) | −0.0023 (19) |
C6 | 0.013 (2) | 0.016 (3) | 0.012 (3) | 0.004 (2) | −0.001 (2) | −0.003 (2) |
C7 | 0.013 (2) | 0.013 (3) | 0.014 (3) | 0.0051 (19) | 0.000 (2) | 0.002 (2) |
C8 | 0.013 (2) | 0.019 (3) | 0.016 (3) | 0.004 (2) | 0.002 (2) | 0.000 (2) |
C9 | 0.016 (3) | 0.017 (3) | 0.029 (4) | 0.002 (2) | 0.011 (3) | 0.002 (3) |
C10 | 0.016 (3) | 0.016 (3) | 0.023 (3) | 0.000 (2) | 0.005 (2) | 0.005 (2) |
Bi1—Cl1 | 2.6812 (12) | C3—H3 | 0.9500 |
Bi1—Cl2 | 2.7986 (14) | C4—C5 | 1.337 (8) |
Bi1—Cl3 | 2.8899 (12) | C4—H41 | 0.9500 |
Bi1—Cl4 | 2.6970 (13) | C5—H5 | 0.9500 |
Bi1—Cl5 | 2.6312 (13) | N4—C6 | 1.342 (6) |
Bi1—Cl6 | 2.5896 (12) | N4—C10 | 1.348 (6) |
O1—H11 | 0.837 (10) | N4—H4 | 0.8800 |
O1—H12 | 0.836 (10) | N5—C6 | 1.335 (6) |
N1—C1 | 1.346 (7) | N5—H51 | 0.8800 |
N1—C5 | 1.373 (7) | N5—H52 | 0.8800 |
N1—H1 | 0.8800 | N6—C7 | 1.455 (6) |
N2—C1 | 1.331 (6) | N6—H61 | 0.9100 |
N2—H21 | 0.8800 | N6—H62 | 0.9100 |
N2—H22 | 0.8800 | N6—H63 | 0.9100 |
N3—C2 | 1.454 (6) | C6—C7 | 1.418 (7) |
N3—H31 | 0.9100 | C7—C8 | 1.367 (6) |
N3—H32 | 0.9100 | C8—C9 | 1.385 (7) |
N3—H33 | 0.9100 | C8—H8 | 0.9500 |
C1—C2 | 1.415 (7) | C9—C10 | 1.364 (7) |
C2—C3 | 1.360 (7) | C9—H9 | 0.9500 |
C3—C4 | 1.414 (7) | C10—H10 | 0.9500 |
Cl6—Bi1—Cl5 | 88.69 (4) | C2—C3—H3 | 120.3 |
Cl6—Bi1—Cl1 | 88.51 (4) | C4—C3—H3 | 120.3 |
Cl5—Bi1—Cl1 | 85.39 (4) | C5—C4—C3 | 119.3 (5) |
Cl6—Bi1—Cl4 | 87.53 (4) | C5—C4—H41 | 120.4 |
Cl5—Bi1—Cl4 | 90.58 (4) | C3—C4—H41 | 120.4 |
Cl1—Bi1—Cl4 | 174.42 (4) | C4—C5—N1 | 120.0 (5) |
Cl6—Bi1—Cl2 | 91.56 (4) | C4—C5—H5 | 120.0 |
Cl5—Bi1—Cl2 | 179.68 (4) | N1—C5—H5 | 120.0 |
Cl1—Bi1—Cl2 | 94.42 (4) | C6—N4—C10 | 124.7 (5) |
Cl4—Bi1—Cl2 | 89.62 (4) | C6—N4—H4 | 117.6 |
Cl6—Bi1—Cl3 | 170.83 (4) | C10—N4—H4 | 117.6 |
Cl5—Bi1—Cl3 | 82.16 (4) | C6—N5—H51 | 120.0 |
Cl1—Bi1—Cl3 | 91.37 (4) | C6—N5—H52 | 120.0 |
Cl4—Bi1—Cl3 | 91.91 (4) | H51—N5—H52 | 120.0 |
Cl2—Bi1—Cl3 | 97.59 (4) | C7—N6—H61 | 109.5 |
H11—O1—H12 | 108 (6) | C7—N6—H62 | 109.5 |
C1—N1—C5 | 123.9 (5) | H61—N6—H62 | 109.5 |
C1—N1—H1 | 118.1 | C7—N6—H63 | 109.5 |
C5—N1—H1 | 118.1 | H61—N6—H63 | 109.5 |
C1—N2—H21 | 120.0 | H62—N6—H63 | 109.5 |
C1—N2—H22 | 120.0 | N5—C6—N4 | 119.2 (5) |
H21—N2—H22 | 120.0 | N5—C6—C7 | 125.0 (5) |
C2—N3—H31 | 109.5 | N4—C6—C7 | 115.8 (4) |
C2—N3—H32 | 109.5 | C8—C7—C6 | 120.7 (5) |
H31—N3—H32 | 109.5 | C8—C7—N6 | 120.8 (4) |
C2—N3—H33 | 109.5 | C6—C7—N6 | 118.4 (4) |
H31—N3—H33 | 109.5 | C7—C8—C9 | 120.0 (5) |
H32—N3—H33 | 109.5 | C7—C8—H8 | 120.0 |
N2—C1—N1 | 119.7 (5) | C9—C8—H8 | 120.0 |
N2—C1—C2 | 124.3 (5) | C10—C9—C8 | 119.1 (5) |
N1—C1—C2 | 116.0 (4) | C10—C9—H9 | 120.5 |
C3—C2—C1 | 121.4 (5) | C8—C9—H9 | 120.5 |
C3—C2—N3 | 119.9 (5) | N4—C10—C9 | 119.5 (5) |
C1—C2—N3 | 118.7 (4) | N4—C10—H10 | 120.3 |
C2—C3—C4 | 119.4 (5) | C9—C10—H10 | 120.3 |
C5—N1—C1—N2 | 179.5 (5) | C10—N4—C6—N5 | 177.1 (5) |
C5—N1—C1—C2 | −0.3 (8) | C10—N4—C6—C7 | −2.2 (8) |
N2—C1—C2—C3 | −179.3 (5) | N5—C6—C7—C8 | −176.4 (5) |
N1—C1—C2—C3 | 0.5 (8) | N4—C6—C7—C8 | 2.8 (7) |
N2—C1—C2—N3 | 1.3 (8) | N5—C6—C7—N6 | 3.6 (8) |
N1—C1—C2—N3 | −178.9 (5) | N4—C6—C7—N6 | −177.2 (5) |
C1—C2—C3—C4 | −0.1 (8) | C6—C7—C8—C9 | −0.6 (8) |
N3—C2—C3—C4 | 179.3 (5) | N6—C7—C8—C9 | 179.4 (5) |
C2—C3—C4—C5 | −0.6 (8) | C7—C8—C9—C10 | −2.5 (8) |
C3—C4—C5—N1 | 0.8 (9) | C6—N4—C10—C9 | −0.8 (8) |
C1—N1—C5—C4 | −0.4 (9) | C8—C9—C10—N4 | 3.2 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Cl3i | 0.88 | 2.31 | 3.154 (5) | 160 |
N2—H21···Cl4i | 0.88 | 2.43 | 3.215 (4) | 150 |
N2—H22···Cl7 | 0.88 | 2.35 | 3.223 (5) | 171 |
N3—H31···Cl7ii | 0.91 | 2.68 | 3.202 (5) | 118 |
N3—H32···O1 | 0.91 | 1.94 | 2.848 (6) | 176 |
N3—H33···Cl1iii | 0.91 | 2.37 | 3.228 (5) | 157 |
N4—H4···Cl7iv | 0.88 | 2.35 | 3.181 (4) | 158 |
N5—H51···Cl7iv | 0.88 | 2.70 | 3.453 (5) | 144 |
N5—H52···Cl5iii | 0.88 | 2.43 | 3.290 (5) | 167 |
N6—H61···O1 | 0.91 | 1.91 | 2.794 (6) | 163 |
N6—H62···Cl3iii | 0.91 | 2.29 | 3.167 (4) | 163 |
N6—H63···Cl2 | 0.91 | 2.38 | 3.218 (4) | 153 |
O1—H11···Cl4v | 0.84 (1) | 2.36 (2) | 3.177 (5) | 165 (6) |
O1—H12···Cl6 | 0.84 (1) | 2.26 (2) | 3.083 (4) | 170 (6) |
Symmetry codes: (i) x+1, y+1, z; (ii) −x+2, −y+2, −z+1; (iii) x+1, y, z; (iv) −x+2, −y+1, −z+1; (v) −x+1, −y+1, −z+1. |
(C6H9N2)4[Bi2Cl10] | Z = 1 |
Mr = 1209.07 | F(000) = 572 |
Triclinic, P1 | Dx = 2.109 Mg m−3 |
a = 8.8144 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.9982 (3) Å | Cell parameters from 6026 reflections |
c = 12.3440 (4) Å | θ = 3.2–29.2° |
α = 76.784 (3)° | µ = 9.96 mm−1 |
β = 87.111 (3)° | T = 160 K |
γ = 88.514 (3)° | Block, colourless |
V = 951.80 (6) Å3 | 0.25 × 0.15 × 0.07 mm |
Oxford Diffraction SuperNova dual radiation diffractometer | 4463 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray source | 4137 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.026 |
Detector resolution: 10.3801 pixels mm-1 | θmax = 29.5°, θmin = 2.8° |
ω scans | h = −11→11 |
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2018) | k = −10→11 |
Tmin = 0.660, Tmax = 1.000 | l = −11→16 |
8469 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.024 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.049 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.015P)2] where P = (Fo2 + 2Fc2)/3 |
4463 reflections | (Δ/σ)max < 0.001 |
201 parameters | Δρmax = 0.89 e Å−3 |
54 restraints | Δρmin = −1.03 e Å−3 |
Experimental. Data collection and full structure determination done by Prof. Anthony Linden: anthony.linden@chem.uzh.ch Solvent used: 2M HCl Cooling Device: Oxford Instruments Cryojet XL Crystal mount: on a glass fibre Frames collected: 312 Seconds exposure per frame: 3.0 Degrees rotation per frame: 1.0 Crystal-detector distance (mm): 55.0 Client: Levi Senior Sample code: LS010 |
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. |
Refinement. Rigid body restraints were applied to the atoms of the cation containing atom N3. |
x | y | z | Uiso*/Ueq | ||
Bi1 | 0.50769 (2) | 0.39447 (2) | 0.17732 (2) | 0.01904 (5) | |
Cl1 | 0.50021 (11) | 0.12800 (10) | 0.30547 (8) | 0.0342 (2) | |
Cl2 | 0.53940 (10) | 0.53069 (11) | 0.33900 (8) | 0.0316 (2) | |
Cl3 | 0.80433 (10) | 0.36762 (11) | 0.14781 (9) | 0.0311 (2) | |
Cl4 | 0.19902 (10) | 0.42985 (10) | 0.20710 (8) | 0.0275 (2) | |
Cl5 | 0.47878 (12) | 0.29835 (11) | −0.02343 (8) | 0.0339 (2) | |
N1 | 0.1469 (3) | 0.6424 (3) | 0.3902 (2) | 0.0236 (7) | |
H1 | 0.190004 | 0.588325 | 0.345739 | 0.028* | |
N2 | −0.0854 (3) | 0.5797 (3) | 0.3363 (2) | 0.0241 (7) | |
H21 | −0.037783 | 0.526435 | 0.293025 | 0.029* | |
H22 | −0.185334 | 0.584809 | 0.339472 | 0.029* | |
C1 | −0.0069 (4) | 0.6519 (4) | 0.3964 (3) | 0.0201 (7) | |
C2 | −0.0762 (4) | 0.7402 (4) | 0.4683 (3) | 0.0220 (8) | |
C3 | 0.0177 (4) | 0.8060 (4) | 0.5287 (3) | 0.0270 (8) | |
H31 | −0.026500 | 0.862991 | 0.578447 | 0.032* | |
C4 | 0.1757 (4) | 0.7925 (4) | 0.5199 (3) | 0.0314 (9) | |
H4 | 0.238106 | 0.839019 | 0.562910 | 0.038* | |
C5 | 0.2381 (4) | 0.7110 (4) | 0.4482 (3) | 0.0296 (9) | |
H5 | 0.345384 | 0.702426 | 0.438924 | 0.036* | |
C6 | −0.2452 (4) | 0.7578 (4) | 0.4745 (3) | 0.0290 (9) | |
H61 | −0.280318 | 0.809261 | 0.401056 | 0.044* | |
H62 | −0.274901 | 0.818780 | 0.528682 | 0.044* | |
H63 | −0.291321 | 0.656853 | 0.497726 | 0.044* | |
N3 | 0.1583 (4) | 0.8106 (4) | 0.0943 (3) | 0.0449 (10) | |
H3 | 0.207612 | 0.748010 | 0.059175 | 0.054* | |
N4 | −0.0581 (4) | 0.7233 (4) | 0.0399 (3) | 0.0435 (9) | |
H41 | −0.002586 | 0.663843 | 0.005540 | 0.052* | |
H42 | −0.157750 | 0.722971 | 0.038404 | 0.052* | |
C7 | 0.0078 (5) | 0.8122 (4) | 0.0933 (3) | 0.0361 (9) | |
C8 | −0.0776 (5) | 0.9127 (4) | 0.1492 (3) | 0.0274 (8) | |
C9 | 0.0085 (5) | 1.0004 (5) | 0.1983 (4) | 0.0380 (10) | |
H9 | −0.043656 | 1.069626 | 0.235317 | 0.046* | |
C10 | 0.1659 (6) | 0.9968 (5) | 0.1985 (4) | 0.0499 (12) | |
H10 | 0.218704 | 1.061239 | 0.234552 | 0.060* | |
C11 | 0.2436 (6) | 0.8974 (5) | 0.1452 (4) | 0.0447 (11) | |
H11 | 0.351336 | 0.889422 | 0.143717 | 0.054* | |
C12 | −0.2428 (5) | 0.9150 (5) | 0.1498 (4) | 0.0398 (10) | |
H121 | −0.275546 | 0.939059 | 0.072959 | 0.060* | |
H122 | −0.282958 | 0.992859 | 0.188067 | 0.060* | |
H123 | −0.281062 | 0.814759 | 0.188748 | 0.060* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Bi1 | 0.01407 (8) | 0.02466 (8) | 0.01962 (8) | −0.00037 (5) | −0.00009 (5) | −0.00777 (5) |
Cl1 | 0.0329 (6) | 0.0299 (5) | 0.0370 (6) | 0.0011 (4) | 0.0011 (4) | −0.0027 (4) |
Cl2 | 0.0246 (5) | 0.0464 (6) | 0.0298 (5) | −0.0023 (4) | −0.0013 (4) | −0.0209 (4) |
Cl3 | 0.0145 (4) | 0.0381 (5) | 0.0427 (6) | 0.0007 (4) | 0.0013 (4) | −0.0142 (4) |
Cl4 | 0.0141 (4) | 0.0353 (5) | 0.0360 (6) | 0.0007 (4) | −0.0006 (4) | −0.0143 (4) |
Cl5 | 0.0458 (6) | 0.0310 (5) | 0.0280 (5) | −0.0058 (4) | −0.0029 (4) | −0.0126 (4) |
N1 | 0.0229 (17) | 0.0233 (15) | 0.0240 (17) | 0.0039 (13) | 0.0030 (13) | −0.0054 (12) |
N2 | 0.0221 (16) | 0.0282 (16) | 0.0238 (17) | 0.0011 (13) | 0.0025 (13) | −0.0101 (13) |
C1 | 0.0217 (19) | 0.0178 (17) | 0.0170 (18) | 0.0010 (14) | 0.0022 (14) | 0.0032 (13) |
C2 | 0.026 (2) | 0.0184 (17) | 0.0192 (19) | 0.0037 (15) | 0.0026 (15) | −0.0012 (13) |
C3 | 0.034 (2) | 0.0233 (19) | 0.025 (2) | 0.0027 (16) | −0.0008 (17) | −0.0080 (15) |
C4 | 0.028 (2) | 0.029 (2) | 0.040 (3) | 0.0005 (17) | −0.0092 (18) | −0.0118 (17) |
C5 | 0.021 (2) | 0.027 (2) | 0.038 (2) | −0.0004 (16) | −0.0019 (17) | −0.0014 (17) |
C6 | 0.025 (2) | 0.031 (2) | 0.032 (2) | 0.0051 (16) | 0.0019 (17) | −0.0095 (16) |
N3 | 0.033 (2) | 0.035 (2) | 0.054 (3) | 0.0113 (15) | 0.0176 (18) | 0.0107 (16) |
N4 | 0.061 (3) | 0.0355 (19) | 0.036 (2) | −0.0048 (18) | 0.0116 (18) | −0.0150 (16) |
C7 | 0.047 (2) | 0.024 (2) | 0.032 (2) | −0.0013 (17) | 0.0063 (19) | 0.0032 (16) |
C8 | 0.034 (2) | 0.0230 (18) | 0.023 (2) | 0.0018 (16) | 0.0053 (16) | −0.0009 (14) |
C9 | 0.039 (2) | 0.033 (2) | 0.038 (3) | −0.0009 (18) | −0.003 (2) | 0.0019 (18) |
C10 | 0.052 (3) | 0.049 (3) | 0.045 (3) | −0.016 (2) | −0.015 (2) | 0.002 (2) |
C11 | 0.046 (3) | 0.036 (2) | 0.043 (3) | −0.002 (2) | 0.004 (2) | 0.0077 (19) |
C12 | 0.037 (2) | 0.043 (3) | 0.039 (3) | −0.001 (2) | 0.001 (2) | −0.010 (2) |
Bi1—Cl1 | 2.5533 (10) | C6—H61 | 0.9800 |
Bi1—Cl2 | 2.5992 (9) | C6—H62 | 0.9800 |
Bi1—Cl3 | 2.6342 (9) | C6—H63 | 0.9800 |
Bi1—Cl4 | 2.7471 (8) | N3—C7 | 1.327 (5) |
Bi1—Cl5 | 2.8300 (9) | N3—C11 | 1.368 (6) |
Bi1—Cl5i | 2.9760 (10) | N3—H3 | 0.8800 |
N1—C5 | 1.351 (5) | N4—C7 | 1.310 (5) |
N1—C1 | 1.356 (4) | N4—H41 | 0.8800 |
N1—H1 | 0.8800 | N4—H42 | 0.8800 |
N2—C1 | 1.323 (4) | C7—C8 | 1.435 (5) |
N2—H21 | 0.8800 | C8—C9 | 1.364 (6) |
N2—H22 | 0.8800 | C8—C12 | 1.455 (6) |
C1—C2 | 1.426 (5) | C9—C10 | 1.387 (6) |
C2—C3 | 1.372 (5) | C9—H9 | 0.9500 |
C2—C6 | 1.494 (5) | C10—C11 | 1.377 (6) |
C3—C4 | 1.396 (5) | C10—H10 | 0.9500 |
C3—H31 | 0.9500 | C11—H11 | 0.9500 |
C4—C5 | 1.360 (5) | C12—H121 | 0.9800 |
C4—H4 | 0.9500 | C12—H122 | 0.9800 |
C5—H5 | 0.9500 | C12—H123 | 0.9800 |
Cl1—Bi1—Cl2 | 93.93 (3) | N1—C5—H5 | 120.1 |
Cl1—Bi1—Cl3 | 90.08 (3) | C4—C5—H5 | 120.1 |
Cl2—Bi1—Cl3 | 91.38 (3) | C2—C6—H61 | 109.5 |
Cl1—Bi1—Cl4 | 91.13 (3) | C2—C6—H62 | 109.5 |
Cl2—Bi1—Cl4 | 87.92 (3) | H61—C6—H62 | 109.5 |
Cl3—Bi1—Cl4 | 178.64 (3) | C2—C6—H63 | 109.5 |
Cl1—Bi1—Cl5 | 96.18 (3) | H61—C6—H63 | 109.5 |
Cl2—Bi1—Cl5 | 169.86 (3) | H62—C6—H63 | 109.5 |
Cl3—Bi1—Cl5 | 87.88 (3) | C7—N3—C11 | 125.8 (4) |
Cl4—Bi1—Cl5 | 92.59 (3) | C7—N3—H3 | 117.1 |
Cl1—Bi1—Cl5i | 178.47 (3) | C11—N3—H3 | 117.1 |
Cl2—Bi1—Cl5i | 87.27 (3) | C7—N4—H41 | 120.0 |
Cl3—Bi1—Cl5i | 88.94 (3) | C7—N4—H42 | 120.0 |
Cl4—Bi1—Cl5i | 89.86 (3) | H41—N4—H42 | 120.0 |
Cl5—Bi1—Cl5i | 82.60 (3) | N4—C7—N3 | 118.8 (4) |
Bi1—Cl5—Bi1i | 97.40 (3) | N4—C7—C8 | 122.1 (4) |
C5—N1—C1 | 124.0 (3) | N3—C7—C8 | 119.1 (4) |
C5—N1—H1 | 118.0 | C9—C8—C7 | 114.6 (4) |
C1—N1—H1 | 118.0 | C9—C8—C12 | 125.5 (4) |
C1—N2—H21 | 120.0 | C7—C8—C12 | 119.8 (4) |
C1—N2—H22 | 120.0 | C8—C9—C10 | 125.4 (4) |
H21—N2—H22 | 120.0 | C8—C9—H9 | 117.3 |
N2—C1—N1 | 119.0 (3) | C10—C9—H9 | 117.3 |
N2—C1—C2 | 123.1 (3) | C11—C10—C9 | 118.2 (5) |
N1—C1—C2 | 117.9 (3) | C11—C10—H10 | 120.9 |
C3—C2—C1 | 117.5 (3) | C9—C10—H10 | 120.9 |
C3—C2—C6 | 123.1 (3) | N3—C11—C10 | 116.8 (4) |
C1—C2—C6 | 119.5 (3) | N3—C11—H11 | 121.6 |
C2—C3—C4 | 122.6 (3) | C10—C11—H11 | 121.6 |
C2—C3—H31 | 118.7 | C8—C12—H121 | 109.5 |
C4—C3—H31 | 118.7 | C8—C12—H122 | 109.5 |
C5—C4—C3 | 118.3 (4) | H121—C12—H122 | 109.5 |
C5—C4—H4 | 120.8 | C8—C12—H123 | 109.5 |
C3—C4—H4 | 120.8 | H121—C12—H123 | 109.5 |
N1—C5—C4 | 119.7 (3) | H122—C12—H123 | 109.5 |
C5—N1—C1—N2 | −179.8 (3) | C11—N3—C7—N4 | 179.3 (4) |
C5—N1—C1—C2 | 0.2 (5) | C11—N3—C7—C8 | 0.2 (6) |
N2—C1—C2—C3 | 178.2 (3) | N4—C7—C8—C9 | −178.4 (4) |
N1—C1—C2—C3 | −1.8 (5) | N3—C7—C8—C9 | 0.7 (6) |
N2—C1—C2—C6 | −2.1 (5) | N4—C7—C8—C12 | 1.5 (6) |
N1—C1—C2—C6 | 177.9 (3) | N3—C7—C8—C12 | −179.4 (4) |
C1—C2—C3—C4 | 1.6 (5) | C7—C8—C9—C10 | −0.9 (6) |
C6—C2—C3—C4 | −178.1 (3) | C12—C8—C9—C10 | 179.3 (4) |
C2—C3—C4—C5 | 0.2 (6) | C8—C9—C10—C11 | 0.1 (7) |
C1—N1—C5—C4 | 1.6 (6) | C7—N3—C11—C10 | −1.0 (7) |
C3—C4—C5—N1 | −1.8 (6) | C9—C10—C11—N3 | 0.9 (6) |
Symmetry code: (i) −x+1, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Cl4 | 0.88 | 2.46 | 3.287 (3) | 156 |
N2—H21···Cl4 | 0.88 | 2.52 | 3.324 (3) | 153 |
N2—H22···Cl2ii | 0.88 | 2.49 | 3.345 (3) | 165 |
N3—H3···Cl5i | 0.88 | 2.81 | 3.451 (4) | 131 |
N4—H41···Cl3i | 0.88 | 2.57 | 3.360 (3) | 150 |
N4—H42···Cl5iii | 0.88 | 2.86 | 3.737 (4) | 175 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1, y, z; (iii) −x, −y+1, −z. |
(C6H9N2)4[Bi2Br10] | Z = 1 |
Mr = 1653.67 | F(000) = 752 |
Triclinic, P1 | Dx = 2.692 Mg m−3 |
a = 9.2145 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.0678 (2) Å | Cell parameters from 11813 reflections |
c = 12.6314 (4) Å | θ = 3.2–29.1° |
α = 75.476 (3)° | µ = 18.43 mm−1 |
β = 86.926 (3)° | T = 160 K |
γ = 89.221 (2)° | Needle, yellow |
V = 1020.22 (5) Å3 | 0.15 × 0.14 × 0.07 mm |
Oxford Diffraction SuperNova dual radiation diffractometer | 5122 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray source | 4575 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.046 |
Detector resolution: 10.3801 pixels mm-1 | θmax = 29.6°, θmin = 2.8° |
ω scans | h = −12→12 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2018) | k = −12→11 |
Tmin = 0.274, Tmax = 1.000 | l = −17→17 |
22534 measured reflections |
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)] = 0.028 | H-atom parameters constrained |
wR(F2) = 0.059 | w = 1/[σ2(Fo2) + (0.0239P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
5122 reflections | Δρmax = 1.52 e Å−3 |
202 parameters | Δρmin = −1.77 e Å−3 |
0 restraints | Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: dual | Extinction coefficient: 0.00191 (12) |
Experimental. Data collection and full structure determination done by Prof. Anthony Linden: anthony.linden@chem.uzh.ch Solvent used: 2M HBr Cooling Device: Oxford Instruments Cryojet XL Crystal mount: on a glass fibre Frames collected: 779 Seconds exposure per frame: 4.0 Degrees rotation per frame: 1.0 Crystal-detector distance (mm): 55.0 Client: Levi Senior Sample code: LS015 |
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 | 0.50924 (2) | 0.39135 (2) | 0.18009 (2) | 0.01729 (6) | |
Br1 | 0.49907 (5) | 0.10892 (4) | 0.31794 (3) | 0.03099 (11) | |
Br2 | 0.54101 (5) | 0.53721 (5) | 0.34378 (3) | 0.03024 (11) | |
Br3 | 0.80913 (4) | 0.36706 (5) | 0.14958 (4) | 0.02761 (10) | |
Br4 | 0.19658 (4) | 0.42565 (5) | 0.20682 (3) | 0.02398 (10) | |
Br5 | 0.47475 (5) | 0.28502 (5) | −0.02029 (3) | 0.02953 (11) | |
N1 | 0.1423 (4) | 0.6474 (4) | 0.3917 (3) | 0.0233 (7) | |
H1 | 0.182106 | 0.594938 | 0.347717 | 0.028* | |
N2 | −0.0819 (4) | 0.5842 (4) | 0.3417 (3) | 0.0236 (7) | |
H21 | −0.038140 | 0.531909 | 0.299312 | 0.028* | |
H22 | −0.177440 | 0.589217 | 0.346206 | 0.028* | |
C1 | −0.0037 (4) | 0.6559 (4) | 0.3992 (3) | 0.0186 (8) | |
C2 | −0.0686 (4) | 0.7419 (4) | 0.4696 (3) | 0.0203 (8) | |
C3 | 0.0223 (5) | 0.8057 (4) | 0.5276 (3) | 0.0261 (9) | |
H31 | −0.018820 | 0.860328 | 0.576999 | 0.031* | |
C4 | 0.1735 (5) | 0.7937 (5) | 0.5173 (4) | 0.0307 (10) | |
H4 | 0.233970 | 0.840133 | 0.558282 | 0.037* | |
C5 | 0.2323 (5) | 0.7145 (5) | 0.4475 (4) | 0.0302 (10) | |
H5 | 0.334778 | 0.706145 | 0.437882 | 0.036* | |
C6 | −0.2303 (5) | 0.7586 (5) | 0.4778 (3) | 0.0287 (10) | |
H61 | −0.264979 | 0.808926 | 0.405592 | 0.043* | |
H62 | −0.256672 | 0.820236 | 0.529537 | 0.043* | |
H63 | −0.275192 | 0.657767 | 0.503642 | 0.043* | |
N3 | 0.1565 (5) | 0.8165 (4) | 0.0970 (3) | 0.0442 (11) | |
H3 | 0.203006 | 0.755442 | 0.062552 | 0.053* | |
N4 | −0.0543 (5) | 0.7318 (4) | 0.0450 (3) | 0.0449 (11) | |
H41 | −0.003796 | 0.673130 | 0.010658 | 0.054* | |
H42 | −0.149760 | 0.732884 | 0.044756 | 0.054* | |
C7 | 0.0126 (6) | 0.8173 (5) | 0.0962 (4) | 0.0335 (11) | |
C8 | −0.0674 (5) | 0.9164 (4) | 0.1518 (3) | 0.0259 (9) | |
C9 | 0.0146 (5) | 1.0014 (5) | 0.1998 (4) | 0.0341 (11) | |
H9 | −0.034406 | 1.068018 | 0.237036 | 0.041* | |
C10 | 0.1645 (6) | 0.9982 (6) | 0.1983 (4) | 0.0490 (15) | |
H10 | 0.215978 | 1.061851 | 0.232809 | 0.059* | |
C11 | 0.2389 (6) | 0.9005 (5) | 0.1457 (4) | 0.0445 (13) | |
H11 | 0.341889 | 0.892861 | 0.143944 | 0.053* | |
C12 | −0.2276 (5) | 0.9185 (5) | 0.1540 (4) | 0.0398 (12) | |
H121 | −0.259677 | 0.944393 | 0.078855 | 0.060* | |
H122 | −0.264395 | 0.994630 | 0.191737 | 0.060* | |
H123 | −0.265109 | 0.817750 | 0.192919 | 0.060* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Bi1 | 0.01270 (9) | 0.02202 (9) | 0.01806 (9) | 0.00003 (6) | −0.00008 (6) | −0.00686 (6) |
Br1 | 0.0271 (3) | 0.0268 (2) | 0.0350 (3) | 0.00156 (19) | 0.0008 (2) | −0.00079 (19) |
Br2 | 0.0243 (2) | 0.0457 (3) | 0.0272 (2) | −0.0019 (2) | −0.00147 (18) | −0.02122 (19) |
Br3 | 0.0127 (2) | 0.0323 (2) | 0.0384 (2) | 0.00028 (17) | 0.00157 (18) | −0.01046 (19) |
Br4 | 0.0124 (2) | 0.0303 (2) | 0.0308 (2) | 0.00217 (16) | −0.00031 (17) | −0.01082 (17) |
Br5 | 0.0410 (3) | 0.0264 (2) | 0.0239 (2) | −0.00511 (19) | −0.00182 (19) | −0.01101 (17) |
N1 | 0.022 (2) | 0.0224 (17) | 0.0241 (17) | 0.0033 (14) | 0.0047 (15) | −0.0044 (14) |
N2 | 0.023 (2) | 0.0247 (17) | 0.0255 (18) | 0.0037 (14) | 0.0000 (15) | −0.0101 (14) |
C1 | 0.022 (2) | 0.0142 (18) | 0.0164 (18) | 0.0039 (16) | −0.0002 (16) | 0.0020 (14) |
C2 | 0.022 (2) | 0.0163 (18) | 0.0195 (19) | 0.0019 (16) | −0.0004 (17) | 0.0000 (15) |
C3 | 0.034 (3) | 0.020 (2) | 0.023 (2) | 0.0015 (18) | −0.0022 (19) | −0.0051 (17) |
C4 | 0.026 (3) | 0.030 (2) | 0.038 (3) | −0.0017 (19) | −0.011 (2) | −0.010 (2) |
C5 | 0.022 (2) | 0.030 (2) | 0.035 (2) | −0.0020 (19) | −0.004 (2) | −0.0022 (19) |
C6 | 0.026 (3) | 0.034 (2) | 0.029 (2) | 0.0040 (19) | 0.0025 (19) | −0.0127 (19) |
N3 | 0.039 (3) | 0.033 (2) | 0.049 (3) | 0.0100 (19) | 0.018 (2) | 0.0064 (19) |
N4 | 0.064 (3) | 0.037 (2) | 0.036 (2) | −0.010 (2) | 0.014 (2) | −0.0153 (19) |
C7 | 0.044 (3) | 0.023 (2) | 0.027 (2) | −0.006 (2) | 0.008 (2) | 0.0039 (18) |
C8 | 0.036 (3) | 0.021 (2) | 0.019 (2) | 0.0014 (19) | −0.0012 (19) | −0.0025 (16) |
C9 | 0.029 (3) | 0.033 (2) | 0.037 (3) | 0.004 (2) | −0.006 (2) | 0.001 (2) |
C10 | 0.056 (4) | 0.036 (3) | 0.050 (3) | −0.012 (3) | −0.021 (3) | 0.004 (2) |
C11 | 0.044 (3) | 0.032 (3) | 0.048 (3) | −0.002 (2) | 0.008 (3) | 0.005 (2) |
C12 | 0.033 (3) | 0.044 (3) | 0.041 (3) | −0.001 (2) | 0.001 (2) | −0.009 (2) |
Bi1—Br1 | 2.7114 (4) | C6—H61 | 0.9800 |
Bi1—Br2 | 2.7491 (4) | C6—H62 | 0.9800 |
Bi1—Br3 | 2.7830 (4) | C6—H63 | 0.9800 |
Bi1—Br4 | 2.9043 (4) | N3—C7 | 1.327 (6) |
Bi1—Br5 | 2.9590 (4) | N3—C11 | 1.355 (7) |
Bi1—Br5i | 3.1172 (4) | N3—H3 | 0.8800 |
N1—C1 | 1.347 (5) | N4—C7 | 1.306 (6) |
N1—C5 | 1.360 (5) | N4—H41 | 0.8800 |
N1—H1 | 0.8800 | N4—H42 | 0.8800 |
N2—C1 | 1.331 (5) | C7—C8 | 1.445 (6) |
N2—H21 | 0.8800 | C8—C9 | 1.354 (6) |
N2—H22 | 0.8800 | C8—C12 | 1.475 (6) |
C1—C2 | 1.426 (5) | C9—C10 | 1.381 (7) |
C2—C3 | 1.366 (6) | C9—H9 | 0.9500 |
C2—C6 | 1.497 (6) | C10—C11 | 1.388 (8) |
C3—C4 | 1.397 (6) | C10—H10 | 0.9500 |
C3—H31 | 0.9500 | C11—H11 | 0.9500 |
C4—C5 | 1.357 (6) | C12—H121 | 0.9800 |
C4—H4 | 0.9500 | C12—H122 | 0.9800 |
C5—H5 | 0.9500 | C12—H123 | 0.9800 |
Br1—Bi1—Br2 | 94.306 (14) | C4—C5—H5 | 120.5 |
Br1—Bi1—Br3 | 90.383 (13) | N1—C5—H5 | 120.5 |
Br2—Bi1—Br3 | 91.286 (13) | C2—C6—H61 | 109.5 |
Br1—Bi1—Br4 | 91.388 (13) | C2—C6—H62 | 109.5 |
Br2—Bi1—Br4 | 88.747 (13) | H61—C6—H62 | 109.5 |
Br3—Bi1—Br4 | 178.221 (12) | C2—C6—H63 | 109.5 |
Br1—Bi1—Br5 | 95.067 (13) | H61—C6—H63 | 109.5 |
Br2—Bi1—Br5 | 170.620 (13) | H62—C6—H63 | 109.5 |
Br3—Bi1—Br5 | 89.036 (13) | C7—N3—C11 | 126.4 (5) |
Br4—Bi1—Br5 | 90.642 (13) | C7—N3—H3 | 116.8 |
Br1—Bi1—Br5i | 179.186 (13) | C11—N3—H3 | 116.8 |
Br2—Bi1—Br5i | 85.969 (13) | C7—N4—H41 | 120.0 |
Br3—Bi1—Br5i | 88.844 (13) | C7—N4—H42 | 120.0 |
Br4—Bi1—Br5i | 89.383 (13) | H41—N4—H42 | 120.0 |
Br5—Bi1—Br5i | 84.665 (12) | N4—C7—N3 | 120.5 (5) |
Bi1—Br5—Bi1i | 95.335 (12) | N4—C7—C8 | 121.2 (5) |
C1—N1—C5 | 124.3 (4) | N3—C7—C8 | 118.3 (4) |
C1—N1—H1 | 117.9 | C9—C8—C7 | 115.4 (4) |
C5—N1—H1 | 117.9 | C9—C8—C12 | 124.8 (4) |
C1—N2—H21 | 120.0 | C7—C8—C12 | 119.8 (4) |
C1—N2—H22 | 120.0 | C8—C9—C10 | 124.6 (5) |
H21—N2—H22 | 120.0 | C8—C9—H9 | 117.7 |
N2—C1—N1 | 119.4 (3) | C10—C9—H9 | 117.7 |
N2—C1—C2 | 122.5 (4) | C9—C10—C11 | 118.9 (5) |
N1—C1—C2 | 118.0 (4) | C9—C10—H10 | 120.5 |
C3—C2—C1 | 117.4 (4) | C11—C10—H10 | 120.5 |
C3—C2—C6 | 122.7 (4) | N3—C11—C10 | 116.3 (5) |
C1—C2—C6 | 119.9 (4) | N3—C11—H11 | 121.8 |
C2—C3—C4 | 122.6 (4) | C10—C11—H11 | 121.8 |
C2—C3—H31 | 118.7 | C8—C12—H121 | 109.5 |
C4—C3—H31 | 118.7 | C8—C12—H122 | 109.5 |
C5—C4—C3 | 118.7 (4) | H121—C12—H122 | 109.5 |
C5—C4—H4 | 120.6 | C8—C12—H123 | 109.5 |
C3—C4—H4 | 120.6 | H121—C12—H123 | 109.5 |
C4—C5—N1 | 119.0 (4) | H122—C12—H123 | 109.5 |
C5—N1—C1—N2 | −179.2 (4) | C11—N3—C7—N4 | 179.2 (4) |
C5—N1—C1—C2 | 0.6 (5) | C11—N3—C7—C8 | 0.1 (7) |
N2—C1—C2—C3 | 177.6 (3) | N4—C7—C8—C9 | −178.6 (4) |
N1—C1—C2—C3 | −2.2 (5) | N3—C7—C8—C9 | 0.4 (6) |
N2—C1—C2—C6 | −2.2 (6) | N4—C7—C8—C12 | 1.8 (6) |
N1—C1—C2—C6 | 178.0 (3) | N3—C7—C8—C12 | −179.1 (4) |
C1—C2—C3—C4 | 2.2 (6) | C7—C8—C9—C10 | −0.1 (7) |
C6—C2—C3—C4 | −178.0 (4) | C12—C8—C9—C10 | 179.4 (4) |
C2—C3—C4—C5 | −0.6 (6) | C8—C9—C10—C11 | −0.8 (7) |
C3—C4—C5—N1 | −1.2 (6) | C7—N3—C11—C10 | −1.0 (7) |
C1—N1—C5—C4 | 1.2 (6) | C9—C10—C11—N3 | 1.3 (7) |
Symmetry code: (i) −x+1, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Br4 | 0.88 | 2.62 | 3.456 (3) | 158 |
N2—H21···Br4 | 0.88 | 2.68 | 3.496 (3) | 154 |
N2—H22···Br2ii | 0.88 | 2.65 | 3.504 (4) | 165 |
N3—H3···Br5i | 0.88 | 3.02 | 3.653 (4) | 130 |
N4—H41···Br3i | 0.88 | 2.72 | 3.521 (4) | 152 |
N4—H42···Br5iii | 0.88 | 3.04 | 3.912 (5) | 173 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1, y, z; (iii) −x, −y+1, −z. |
(C5H9N3)2[Bi2Cl10]·2H2O | F(000) = 1904 |
Mr = 1030.79 | Dx = 2.409 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 18.0583 (2) Å | Cell parameters from 20128 reflections |
b = 12.07450 (12) Å | θ = 3.4–29.4° |
c = 13.43800 (15) Å | µ = 13.33 mm−1 |
β = 104.0805 (11)° | T = 160 K |
V = 2842.05 (5) Å3 | Block, colourless |
Z = 4 | 0.20 × 0.18 × 0.08 mm |
Oxford Diffraction SuperNova dual radiation diffractometer | 3742 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray source | 3505 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.034 |
Detector resolution: 10.3801 pixels mm-1 | θmax = 29.5°, θmin = 2.7° |
ω scans | h = −24→24 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2018) | k = −16→16 |
Tmin = 0.348, Tmax = 1.000 | l = −18→17 |
30758 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: geom & difmap |
R[F2 > 2σ(F2)] = 0.016 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.030 | w = 1/[σ2(Fo2) + (0.0104P)2 + 2.6097P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.003 |
3742 reflections | Δρmax = 0.66 e Å−3 |
182 parameters | Δρmin = −0.55 e Å−3 |
12 restraints | Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: dual | Extinction coefficient: 0.000247 (12) |
Experimental. Data collection and full structure determination done by Prof. Anthony Linden: anthony.linden@chem.uzh.ch Solvent used: 2M HCl Cooling Device: Oxford Instruments Cryojet XL Crystal mount: on a glass fibre Frames collected: 817 Seconds exposure per frame: 8.0 Degrees rotation per frame: 1.0 Crystal-detector distance (mm): 55.0 Client: Levi Senior Sample code: LS033 |
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. |
Refinement. Anion sites across a centre of inversion. Two sites for water molecules disordered about twofold axes. Distance and angle restraints applied to the water H atoms. Distance restraints applied to all N-H H atoms. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Bi1 | 0.35117 (2) | 0.72988 (2) | −0.05830 (2) | 0.01728 (3) | |
Cl1 | 0.46209 (3) | 0.86237 (5) | −0.03702 (5) | 0.03036 (13) | |
Cl2 | 0.40227 (4) | 0.59985 (5) | −0.18555 (4) | 0.03157 (14) | |
Cl3 | 0.27578 (3) | 0.85878 (4) | −0.21265 (4) | 0.02234 (11) | |
Cl4 | 0.42774 (3) | 0.60321 (4) | 0.10076 (4) | 0.02130 (11) | |
Cl5 | 0.30319 (3) | 0.86838 (5) | 0.08236 (4) | 0.02636 (12) | |
N1 | 0.61203 (12) | 0.66820 (18) | −0.07273 (15) | 0.0298 (5) | |
H1 | 0.6008 (16) | 0.6206 (19) | −0.1237 (16) | 0.048 (9)* | |
N2 | 0.60265 (10) | 0.68466 (17) | 0.19552 (14) | 0.0213 (4) | |
H21 | 0.5785 (14) | 0.6189 (13) | 0.190 (2) | 0.040 (8)* | |
H22 | 0.5709 (13) | 0.7352 (17) | 0.213 (2) | 0.033 (8)* | |
H23 | 0.6480 (8) | 0.679 (2) | 0.2424 (15) | 0.031 (7)* | |
N3 | 0.66863 (13) | 0.89037 (18) | 0.16324 (18) | 0.0349 (5) | |
H31 | 0.6629 (16) | 0.876 (2) | 0.2255 (11) | 0.046 (9)* | |
H32 | 0.6898 (17) | 0.9524 (15) | 0.152 (2) | 0.062 (10)* | |
C1 | 0.59972 (12) | 0.64156 (19) | 0.01852 (16) | 0.0230 (5) | |
H11 | 0.577815 | 0.571984 | 0.027900 | 0.028* | |
C2 | 0.61865 (12) | 0.71426 (17) | 0.09767 (16) | 0.0186 (4) | |
C3 | 0.65074 (12) | 0.81845 (19) | 0.08692 (17) | 0.0227 (5) | |
C4 | 0.66180 (13) | 0.8418 (2) | −0.01215 (19) | 0.0303 (5) | |
H4 | 0.683158 | 0.910721 | −0.024913 | 0.036* | |
C5 | 0.64214 (15) | 0.7667 (2) | −0.0878 (2) | 0.0334 (6) | |
H5 | 0.649733 | 0.783718 | −0.153616 | 0.040* | |
O1 | 0.5074 (3) | 0.8331 (3) | 0.2772 (2) | 0.0267 (8) | 0.5 |
H1A | 0.532 (3) | 0.846 (4) | 0.3376 (15) | 0.040* | 0.5 |
H1B | 0.503 (5) | 0.889 (2) | 0.239 (3) | 0.040* | 0.5 |
O2 | 0.4782 (2) | 1.0460 (4) | 0.2339 (6) | 0.0560 (17) | 0.5 |
H2A | 0.4319 (12) | 1.062 (6) | 0.223 (6) | 0.084* | 0.5 |
H2B | 0.502 (3) | 1.089 (5) | 0.204 (5) | 0.084* | 0.5 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Bi1 | 0.01610 (5) | 0.01685 (5) | 0.01932 (5) | 0.00110 (3) | 0.00514 (3) | 0.00141 (3) |
Cl1 | 0.0208 (3) | 0.0294 (3) | 0.0389 (3) | −0.0061 (2) | 0.0032 (2) | 0.0049 (3) |
Cl2 | 0.0496 (4) | 0.0243 (3) | 0.0239 (3) | 0.0113 (3) | 0.0149 (3) | 0.0031 (2) |
Cl3 | 0.0222 (3) | 0.0179 (2) | 0.0242 (3) | −0.0008 (2) | 0.0003 (2) | 0.0013 (2) |
Cl4 | 0.0250 (3) | 0.0189 (3) | 0.0195 (2) | 0.0009 (2) | 0.0044 (2) | −0.0004 (2) |
Cl5 | 0.0290 (3) | 0.0219 (3) | 0.0299 (3) | −0.0061 (2) | 0.0106 (2) | −0.0054 (2) |
N1 | 0.0356 (11) | 0.0328 (12) | 0.0222 (10) | −0.0038 (9) | 0.0092 (9) | −0.0067 (9) |
N2 | 0.0210 (10) | 0.0248 (10) | 0.0177 (9) | −0.0010 (9) | 0.0037 (8) | 0.0018 (8) |
N3 | 0.0453 (13) | 0.0210 (11) | 0.0346 (13) | −0.0111 (10) | 0.0021 (11) | −0.0022 (9) |
C1 | 0.0225 (11) | 0.0235 (12) | 0.0228 (11) | −0.0024 (9) | 0.0054 (9) | −0.0002 (9) |
C2 | 0.0170 (10) | 0.0203 (11) | 0.0182 (10) | 0.0015 (8) | 0.0038 (8) | 0.0046 (8) |
C3 | 0.0198 (11) | 0.0205 (12) | 0.0247 (11) | −0.0004 (9) | −0.0007 (9) | 0.0024 (9) |
C4 | 0.0276 (12) | 0.0292 (13) | 0.0331 (13) | −0.0053 (10) | 0.0057 (10) | 0.0121 (11) |
C5 | 0.0315 (14) | 0.0452 (16) | 0.0261 (13) | −0.0016 (12) | 0.0118 (11) | 0.0083 (11) |
O1 | 0.030 (2) | 0.0257 (17) | 0.023 (2) | 0.0002 (16) | 0.003 (2) | 0.0021 (12) |
O2 | 0.069 (5) | 0.044 (2) | 0.064 (5) | 0.016 (2) | 0.034 (4) | 0.017 (3) |
Bi1—Cl1 | 2.5247 (5) | N3—H31 | 0.885 (10) |
Bi1—Cl2 | 2.6474 (5) | N3—H32 | 0.871 (10) |
Bi1—Cl3 | 2.6840 (5) | C1—C2 | 1.357 (3) |
Bi1—Cl4 | 2.7170 (5) | C1—H11 | 0.9500 |
Bi1—Cl5 | 2.8136 (5) | C2—C3 | 1.407 (3) |
Bi1—Cl5i | 2.9738 (5) | C3—C4 | 1.422 (3) |
N1—C1 | 1.338 (3) | C4—C5 | 1.344 (4) |
N1—C5 | 1.344 (3) | C4—H4 | 0.9500 |
N1—H1 | 0.880 (10) | C5—H5 | 0.9500 |
N2—C2 | 1.458 (3) | O1—H1A | 0.839 (10) |
N2—H21 | 0.900 (10) | O1—H1B | 0.840 (10) |
N2—H22 | 0.907 (10) | O2—H2A | 0.837 (10) |
N2—H23 | 0.906 (10) | O2—H2B | 0.842 (10) |
N3—C3 | 1.323 (3) | ||
Cl1—Bi1—Cl2 | 93.29 (2) | H21—N2—H23 | 109 (2) |
Cl1—Bi1—Cl3 | 87.673 (17) | H22—N2—H23 | 113 (2) |
Cl2—Bi1—Cl3 | 92.048 (17) | C3—N3—H31 | 123 (2) |
Cl1—Bi1—Cl4 | 91.700 (17) | C3—N3—H32 | 118 (2) |
Cl2—Bi1—Cl4 | 89.060 (16) | H31—N3—H32 | 120 (3) |
Cl3—Bi1—Cl4 | 178.756 (16) | N1—C1—C2 | 119.8 (2) |
Cl1—Bi1—Cl5 | 84.998 (18) | N1—C1—H11 | 120.1 |
Cl2—Bi1—Cl5 | 177.559 (18) | C2—C1—H11 | 120.1 |
Cl3—Bi1—Cl5 | 89.619 (17) | C1—C2—C3 | 122.0 (2) |
Cl4—Bi1—Cl5 | 89.256 (16) | C1—C2—N2 | 118.75 (19) |
Cl1—Bi1—Cl5i | 164.142 (18) | C3—C2—N2 | 119.26 (19) |
Cl2—Bi1—Cl5i | 99.089 (18) | N3—C3—C2 | 122.4 (2) |
Cl3—Bi1—Cl5i | 82.042 (16) | N3—C3—C4 | 122.2 (2) |
Cl4—Bi1—Cl5i | 98.344 (16) | C2—C3—C4 | 115.4 (2) |
Cl5—Bi1—Cl5i | 82.905 (16) | C5—C4—C3 | 120.2 (2) |
Bi1—Cl5—Bi1i | 97.096 (16) | C5—C4—H4 | 119.9 |
C1—N1—C5 | 121.0 (2) | C3—C4—H4 | 119.9 |
C1—N1—H1 | 119.9 (19) | N1—C5—C4 | 121.7 (2) |
C5—N1—H1 | 119.1 (19) | N1—C5—H5 | 119.1 |
C2—N2—H21 | 110.3 (17) | C4—C5—H5 | 119.1 |
C2—N2—H22 | 110.1 (17) | H1A—O1—H1B | 113.1 (19) |
H21—N2—H22 | 107 (2) | H2A—O2—H2B | 112.9 (19) |
C2—N2—H23 | 107.5 (16) | ||
C5—N1—C1—C2 | −0.8 (3) | N2—C2—C3—C4 | −177.80 (19) |
N1—C1—C2—C3 | 0.4 (3) | N3—C3—C4—C5 | −179.4 (2) |
N1—C1—C2—N2 | 178.2 (2) | C2—C3—C4—C5 | −0.1 (3) |
C1—C2—C3—N3 | 179.3 (2) | C1—N1—C5—C4 | 0.7 (4) |
N2—C2—C3—N3 | 1.5 (3) | C3—C4—C5—N1 | −0.2 (4) |
C1—C2—C3—C4 | 0.0 (3) |
Symmetry code: (i) −x+1/2, −y+3/2, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Cl2ii | 0.88 (1) | 2.56 (2) | 3.300 (2) | 142 (2) |
N1—H1···Cl4iii | 0.88 (1) | 2.78 (2) | 3.356 (2) | 124 (2) |
N2—H21···Cl2iii | 0.90 (1) | 2.67 (2) | 3.438 (2) | 144 (2) |
N2—H21···Cl4 | 0.90 (1) | 2.70 (2) | 3.2570 (19) | 121 (2) |
N2—H22···O1 | 0.91 (1) | 1.98 (1) | 2.879 (5) | 169 (3) |
N2—H22···O1iv | 0.91 (1) | 1.87 (1) | 2.766 (5) | 168 (3) |
N2—H23···Cl3v | 0.91 (1) | 2.28 (1) | 3.1137 (19) | 152 (2) |
N3—H31···Cl5iv | 0.89 (1) | 2.51 (2) | 3.342 (2) | 158 (3) |
N3—H32···Cl3vi | 0.87 (1) | 2.45 (2) | 3.209 (2) | 146 (3) |
O1—H1A···Cl1iv | 0.84 (1) | 2.66 (3) | 3.418 (3) | 151 (5) |
O1—H1B···O2 | 0.84 (1) | 1.94 (4) | 2.661 (5) | 143 (6) |
O2—H2B···Cl1vi | 0.84 (1) | 2.55 (4) | 3.282 (7) | 147 (7) |
Symmetry codes: (ii) −x+1, y, −z−1/2; (iii) −x+1, −y+1, −z; (iv) −x+1, y, −z+1/2; (v) x+1/2, −y+3/2, z+1/2; (vi) −x+1, −y+2, −z. |
(C5H8N3)[BiI4] | F(000) = 1416 |
Mr = 826.72 | Dx = 3.816 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 12.02106 (15) Å | Cell parameters from 19181 reflections |
b = 7.80880 (9) Å | θ = 3.1–30.3° |
c = 15.3298 (2) Å | µ = 20.80 mm−1 |
β = 90.0530 (11)° | T = 160 K |
V = 1439.01 (3) Å3 | Prism, red |
Z = 4 | 0.16 × 0.10 × 0.04 mm |
Oxford Diffraction SuperNova dual radiation diffractometer | 4076 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray source | 3831 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.041 |
Detector resolution: 10.3801 pixels mm-1 | θmax = 30.4°, θmin = 2.9° |
ω scans | h = −15→16 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2018) | k = −11→11 |
Tmin = 0.259, Tmax = 1.000 | l = −21→21 |
35690 measured reflections |
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)] = 0.020 | H-atom parameters constrained |
wR(F2) = 0.040 | w = 1/[σ2(Fo2) + (0.0158P)2 + 1.0108P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.002 |
4076 reflections | Δρmax = 1.21 e Å−3 |
120 parameters | Δρmin = −1.04 e Å−3 |
0 restraints | Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: dual | Extinction coefficient: 0.00085 (3) |
Experimental. Data collection and full structure determination done by Prof. Anthony Linden: anthony.linden@chem.uzh.ch Solvent used: 2M HI Cooling Device: Oxford Instruments Cryojet XL Crystal mount: on a glass fibre Frames collected: 843 Seconds exposure per frame: 4.0 Degrees rotation per frame: 1.0 Crystal-detector distance (mm): 55.0 Client: Levi Senior Sample code: LS014 |
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. |
Refinement. Refined as a pseudomerohedral twin. |
x | y | z | Uiso*/Ueq | ||
Bi1 | 0.50460 (2) | 0.74323 (2) | 0.58217 (2) | 0.01486 (5) | |
I1 | 0.34952 (2) | 0.87654 (3) | 0.71421 (2) | 0.02166 (7) | |
I2 | 0.67606 (2) | 0.60869 (3) | 0.69839 (2) | 0.02465 (7) | |
I3 | 0.64735 (2) | 1.07351 (3) | 0.57417 (2) | 0.01894 (6) | |
I4 | 0.37076 (2) | 0.40914 (3) | 0.58707 (2) | 0.01862 (6) | |
N1 | 0.9263 (3) | 0.8116 (4) | 0.5537 (2) | 0.0208 (7) | |
H1 | 0.866088 | 0.859132 | 0.575544 | 0.025* | |
N2 | 0.8629 (3) | 0.8991 (4) | 0.4191 (3) | 0.0284 (9) | |
H2A | 0.806907 | 0.948964 | 0.445890 | 0.034* | |
H2B | 0.868236 | 0.904688 | 0.361884 | 0.034* | |
N3 | 0.9804 (4) | 0.7490 (5) | 0.6951 (3) | 0.0351 (10) | |
H3A | 0.920276 | 0.801655 | 0.713883 | 0.042* | |
H3B | 1.027092 | 0.703144 | 0.732718 | 0.042* | |
C1 | 0.9402 (3) | 0.8146 (5) | 0.4653 (3) | 0.0210 (9) | |
C2 | 1.0331 (4) | 0.7373 (5) | 0.4300 (3) | 0.0230 (9) | |
H2 | 1.045469 | 0.738032 | 0.368830 | 0.028* | |
C3 | 1.1076 (4) | 0.6590 (5) | 0.4857 (3) | 0.0229 (9) | |
H3 | 1.170743 | 0.602856 | 0.461827 | 0.028* | |
C4 | 1.0934 (3) | 0.6595 (5) | 0.5748 (3) | 0.0218 (9) | |
H4 | 1.146698 | 0.606093 | 0.611665 | 0.026* | |
C5 | 1.0007 (4) | 0.7388 (5) | 0.6103 (3) | 0.0223 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Bi1 | 0.01475 (8) | 0.01618 (7) | 0.01365 (8) | −0.00005 (5) | 0.00050 (6) | −0.00046 (6) |
I1 | 0.02187 (14) | 0.02647 (13) | 0.01666 (13) | 0.00351 (10) | 0.00292 (11) | −0.00414 (10) |
I2 | 0.02031 (14) | 0.02924 (14) | 0.02440 (15) | 0.00093 (11) | −0.00569 (12) | 0.00617 (11) |
I3 | 0.01781 (13) | 0.01897 (12) | 0.02003 (13) | −0.00332 (10) | −0.00335 (11) | 0.00159 (10) |
I4 | 0.01745 (13) | 0.01773 (12) | 0.02070 (14) | −0.00210 (9) | 0.00599 (10) | −0.00229 (10) |
N1 | 0.0154 (17) | 0.0211 (16) | 0.026 (2) | 0.0028 (14) | 0.0027 (14) | −0.0034 (15) |
N2 | 0.025 (2) | 0.0316 (19) | 0.028 (2) | 0.0045 (16) | −0.0034 (17) | 0.0052 (17) |
N3 | 0.035 (3) | 0.049 (2) | 0.021 (2) | 0.0148 (19) | 0.0009 (19) | 0.0006 (18) |
C1 | 0.020 (2) | 0.0187 (19) | 0.024 (2) | −0.0040 (16) | −0.0041 (17) | 0.0000 (17) |
C2 | 0.022 (2) | 0.025 (2) | 0.021 (2) | −0.0032 (16) | 0.0051 (18) | −0.0031 (17) |
C3 | 0.019 (2) | 0.0167 (19) | 0.033 (3) | −0.0024 (16) | 0.0040 (18) | −0.0040 (18) |
C4 | 0.018 (2) | 0.0191 (19) | 0.028 (2) | 0.0007 (16) | −0.0001 (18) | 0.0011 (18) |
C5 | 0.018 (2) | 0.022 (2) | 0.026 (2) | −0.0007 (15) | −0.0005 (19) | 0.0017 (17) |
Bi1—I1 | 2.9432 (3) | N2—H2B | 0.8800 |
Bi1—I2 | 2.9187 (3) | N3—C5 | 1.325 (6) |
Bi1—I3 | 3.1003 (3) | N3—H3A | 0.8800 |
Bi1—I3i | 3.3348 (3) | N3—H3B | 0.8800 |
Bi1—I4 | 3.0660 (3) | C1—C2 | 1.381 (6) |
Bi1—I4ii | 3.2248 (3) | C2—C3 | 1.380 (6) |
N1—C1 | 1.365 (6) | C2—H2 | 0.9500 |
N1—C5 | 1.369 (5) | C3—C4 | 1.376 (6) |
N1—H1 | 0.8800 | C3—H3 | 0.9500 |
N2—C1 | 1.342 (5) | C4—C5 | 1.387 (6) |
N2—H2A | 0.8800 | C4—H4 | 0.9500 |
I2—Bi1—I1 | 98.912 (9) | C1—N2—H2B | 120.0 |
I2—Bi1—I4 | 92.810 (8) | H2A—N2—H2B | 120.0 |
I1—Bi1—I4 | 87.214 (8) | C5—N3—H3A | 120.0 |
I2—Bi1—I3 | 86.160 (8) | C5—N3—H3B | 120.0 |
I1—Bi1—I3 | 94.815 (8) | H3A—N3—H3B | 120.0 |
I4—Bi1—I3 | 177.843 (9) | N2—C1—N1 | 116.6 (4) |
I2—Bi1—I4ii | 91.716 (9) | N2—C1—C2 | 124.6 (4) |
I1—Bi1—I4ii | 168.189 (9) | N1—C1—C2 | 118.7 (4) |
I4—Bi1—I4ii | 87.131 (8) | C3—C2—C1 | 118.4 (4) |
I3—Bi1—I4ii | 91.004 (8) | C3—C2—H2 | 120.8 |
I2—Bi1—I3i | 168.288 (10) | C1—C2—H2 | 120.8 |
I1—Bi1—I3i | 89.748 (8) | C4—C3—C2 | 122.1 (4) |
I4—Bi1—I3i | 95.489 (8) | C4—C3—H3 | 118.9 |
I3—Bi1—I3i | 85.263 (7) | C2—C3—H3 | 118.9 |
I4ii—Bi1—I3i | 80.483 (8) | C3—C4—C5 | 119.4 (4) |
Bi1—I3—Bi1i | 94.738 (7) | C3—C4—H4 | 120.3 |
Bi1—I4—Bi1ii | 92.869 (8) | C5—C4—H4 | 120.3 |
C1—N1—C5 | 123.8 (4) | N3—C5—N1 | 118.5 (4) |
C1—N1—H1 | 118.1 | N3—C5—C4 | 124.1 (4) |
C5—N1—H1 | 118.1 | N1—C5—C4 | 117.5 (4) |
C1—N2—H2A | 120.0 | ||
C5—N1—C1—N2 | −176.4 (4) | C2—C3—C4—C5 | 1.0 (6) |
C5—N1—C1—C2 | 1.4 (6) | C1—N1—C5—N3 | 177.6 (4) |
N2—C1—C2—C3 | 178.1 (4) | C1—N1—C5—C4 | −2.0 (6) |
N1—C1—C2—C3 | 0.5 (6) | C3—C4—C5—N3 | −178.8 (4) |
C1—C2—C3—C4 | −1.7 (6) | C3—C4—C5—N1 | 0.8 (6) |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···I3 | 0.88 | 3.12 | 3.941 (3) | 157 |
N2—H2A···I3 | 0.88 | 2.92 | 3.773 (4) | 165 |
N2—H2B···I1iii | 0.88 | 3.16 | 3.811 (4) | 132 |
N3—H3A···I2iv | 0.88 | 2.98 | 3.754 (4) | 147 |
N3—H3B···I1v | 0.88 | 3.06 | 3.816 (4) | 145 |
Symmetry codes: (iii) x+1/2, −y+3/2, z−1/2; (iv) −x+3/2, y+1/2, −z+3/2; (v) −x+3/2, y−1/2, −z+3/2. |
(C5H7N2)[BiBr4] | F(000) = 1096 |
Mr = 623.75 | Dx = 3.443 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.66220 (15) Å | Cell parameters from 13232 reflections |
b = 14.08143 (19) Å | θ = 3.5–29.3° |
c = 7.35193 (9) Å | µ = 27.89 mm−1 |
β = 94.7149 (13)° | T = 160 K |
V = 1203.25 (3) Å3 | Block, colourless |
Z = 4 | 0.21 × 0.08 × 0.06 mm |
Oxford Diffraction SuperNova dual radiation diffractometer | 3128 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray source | 2794 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.040 |
Detector resolution: 10.3801 pixels mm-1 | θmax = 29.5°, θmin = 2.9° |
ω scans | h = −16→15 |
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2018) | k = −19→19 |
Tmin = 0.735, Tmax = 1.000 | l = −10→9 |
26081 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.023 | Hydrogen site location: geom & difmap |
wR(F2) = 0.050 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0231P)2 + 0.9774P] where P = (Fo2 + 2Fc2)/3 |
3127 reflections | (Δ/σ)max = 0.001 |
121 parameters | Δρmax = 1.26 e Å−3 |
0 restraints | Δρmin = −2.21 e Å−3 |
Experimental. Data collection and full structure determination done by Prof. Anthony Linden: anthony.linden@chem.uzh.ch Solvent used: 2M HBr Cooling Device: Oxford Instruments Cryojet XL Crystal mount: on a glass fibre Frames collected: 813 Seconds exposure per frame: 8.0 Degrees rotation per frame: 1.0 Crystal-detector distance (mm): 55.0 Client: Levi Senior Sample code: LS036 |
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 | 0.26448 (2) | 0.33482 (2) | 0.52386 (2) | 0.01425 (5) | |
Br1 | 0.13501 (3) | 0.47782 (3) | 0.37005 (5) | 0.02171 (10) | |
Br2 | 0.41622 (3) | 0.45100 (3) | 0.69260 (5) | 0.01968 (9) | |
Br3 | 0.11987 (3) | 0.33214 (3) | 0.82384 (5) | 0.01866 (9) | |
Br4 | 0.40032 (3) | 0.32819 (3) | 0.21440 (5) | 0.01834 (9) | |
N1 | 0.1705 (4) | 0.5749 (3) | 0.9120 (6) | 0.0401 (11) | |
H1 | 0.144 (5) | 0.523 (5) | 0.881 (8) | 0.06 (2)* | |
N2 | 0.3249 (4) | 0.8303 (3) | 1.0181 (6) | 0.0306 (9) | |
H21 | 0.285 (5) | 0.878 (5) | 0.978 (8) | 0.059 (19)* | |
H22 | 0.389 (5) | 0.830 (4) | 1.079 (8) | 0.056 (19)* | |
C1 | 0.2767 (5) | 0.5783 (4) | 1.0033 (6) | 0.0393 (13) | |
H11 | 0.314405 | 0.520835 | 1.040512 | 0.047* | |
C2 | 0.3290 (4) | 0.6616 (3) | 1.0414 (6) | 0.0274 (10) | |
H2 | 0.402901 | 0.662979 | 1.106108 | 0.033* | |
C3 | 0.2741 (3) | 0.7471 (3) | 0.9855 (5) | 0.0191 (8) | |
C4 | 0.1635 (3) | 0.7410 (3) | 0.8953 (5) | 0.0237 (9) | |
H4 | 0.122560 | 0.797233 | 0.859612 | 0.028* | |
C5 | 0.1155 (4) | 0.6550 (3) | 0.8594 (6) | 0.0307 (11) | |
H5 | 0.041453 | 0.651245 | 0.795595 | 0.037* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Bi1 | 0.01459 (8) | 0.01259 (9) | 0.01554 (8) | −0.00020 (5) | 0.00109 (6) | 0.00034 (5) |
Br1 | 0.01822 (19) | 0.0174 (2) | 0.0288 (2) | 0.00216 (16) | −0.00217 (16) | 0.00382 (16) |
Br2 | 0.01819 (18) | 0.0172 (2) | 0.0231 (2) | −0.00246 (15) | −0.00186 (15) | −0.00160 (15) |
Br3 | 0.01692 (19) | 0.0173 (2) | 0.0222 (2) | 0.00106 (15) | 0.00430 (15) | 0.00167 (14) |
Br4 | 0.01725 (19) | 0.0181 (2) | 0.01999 (19) | −0.00329 (15) | 0.00321 (15) | −0.00210 (14) |
N1 | 0.062 (3) | 0.020 (2) | 0.042 (2) | −0.017 (2) | 0.025 (2) | −0.0098 (19) |
N2 | 0.025 (2) | 0.027 (2) | 0.038 (2) | −0.0059 (18) | −0.0059 (19) | 0.0008 (18) |
C1 | 0.063 (4) | 0.025 (3) | 0.034 (3) | 0.019 (3) | 0.026 (3) | 0.010 (2) |
C2 | 0.029 (2) | 0.032 (3) | 0.021 (2) | 0.012 (2) | 0.0059 (18) | 0.0051 (18) |
C3 | 0.0204 (19) | 0.021 (2) | 0.0162 (19) | −0.0004 (17) | 0.0027 (15) | 0.0018 (16) |
C4 | 0.022 (2) | 0.023 (2) | 0.026 (2) | 0.0014 (18) | 0.0000 (17) | −0.0011 (17) |
C5 | 0.028 (2) | 0.033 (3) | 0.032 (2) | −0.012 (2) | 0.007 (2) | −0.006 (2) |
Bi1—Br1 | 2.7079 (4) | N2—H21 | 0.85 (6) |
Bi1—Br2 | 2.6431 (4) | N2—H22 | 0.84 (6) |
Bi1—Br3 | 2.8846 (4) | C1—C2 | 1.341 (7) |
Bi1—Br3i | 3.1822 (4) | C1—H11 | 0.9500 |
Bi1—Br4 | 2.8787 (4) | C2—C3 | 1.408 (6) |
Bi1—Br4ii | 3.0620 (4) | C2—H2 | 0.9500 |
N1—C5 | 1.338 (7) | C3—C4 | 1.403 (5) |
N1—C1 | 1.361 (7) | C4—C5 | 1.352 (6) |
N1—H1 | 0.81 (6) | C4—H4 | 0.9500 |
N2—C3 | 1.326 (6) | C5—H5 | 0.9500 |
Br2—Bi1—Br1 | 93.702 (13) | C1—N1—H1 | 118 (4) |
Br2—Bi1—Br4 | 90.017 (12) | C3—N2—H21 | 114 (4) |
Br1—Bi1—Br4 | 91.046 (12) | C3—N2—H22 | 117 (4) |
Br2—Bi1—Br3 | 93.452 (12) | H21—N2—H22 | 128 (6) |
Br1—Bi1—Br3 | 89.314 (12) | C2—C1—N1 | 120.9 (5) |
Br4—Bi1—Br3 | 176.482 (12) | C2—C1—H11 | 119.6 |
Br2—Bi1—Br4ii | 87.020 (12) | N1—C1—H11 | 119.6 |
Br1—Bi1—Br4ii | 176.605 (12) | C1—C2—C3 | 119.9 (5) |
Br4—Bi1—Br4ii | 92.272 (11) | C1—C2—H2 | 120.0 |
Br3—Bi1—Br4ii | 87.331 (11) | C3—C2—H2 | 120.0 |
Br2—Bi1—Br3i | 169.462 (12) | N2—C3—C4 | 121.2 (4) |
Br1—Bi1—Br3i | 95.756 (12) | N2—C3—C2 | 121.1 (4) |
Br4—Bi1—Br3i | 85.182 (11) | C4—C3—C2 | 117.7 (4) |
Br3—Bi1—Br3i | 91.301 (11) | C5—C4—C3 | 119.7 (4) |
Br4ii—Bi1—Br3i | 83.810 (12) | C5—C4—H4 | 120.1 |
Bi1—Br3—Bi1ii | 92.407 (11) | C3—C4—H4 | 120.1 |
Bi1—Br4—Bi1i | 95.064 (11) | N1—C5—C4 | 121.2 (5) |
C5—N1—C1 | 120.6 (4) | N1—C5—H5 | 119.4 |
C5—N1—H1 | 121 (4) | C4—C5—H5 | 119.4 |
C5—N1—C1—C2 | −0.5 (7) | N2—C3—C4—C5 | 178.1 (4) |
N1—C1—C2—C3 | −0.5 (7) | C2—C3—C4—C5 | −2.4 (6) |
C1—C2—C3—N2 | −178.6 (4) | C1—N1—C5—C4 | −0.1 (7) |
C1—C2—C3—C4 | 1.9 (6) | C3—C4—C5—N1 | 1.5 (7) |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Br3 | 0.81 (6) | 2.74 (6) | 3.521 (4) | 163 (6) |
N2—H21···Br1iii | 0.85 (6) | 2.76 (7) | 3.605 (5) | 173 (5) |
N2—H22···Br4iv | 0.84 (6) | 2.78 (6) | 3.620 (4) | 179 (5) |
Symmetry codes: (iii) x, −y+3/2, z+1/2; (iv) −x+1, y+1/2, −z+3/2. |
(2) (X = Cl) | (3) (X = Br) | (4) (X = Cl) | |
Bi1—X1 | 2.5533 (10) | 2.7114 (4) | 2.5247 (5) |
Bi1—X2 | 2.5992 (9) | 2.7491 (4) | 2.6474 (5) |
Bi1—X3 | 2.6342 (9) | 2.7830 (4) | 2.6840 (5) |
Bi1—X4 | 2.7471 (8) | 2.9043 (4) | 2.7170 (5) |
Bi1—X5 | 2.8300 (9) | 2.9590 (4) | 2.8136 (5) |
Bi1—X5i | 2.9760 (10) | 3.1172 (4) | 2.9738 (6) |
N2—C1 | 1.323 (4) | 1.331 (5) | – |
N4—C7 | 1.310 (5) | 1.306 (6) | – |
N2—C2 | – | – | 1.458 (3) |
N3—C3 | – | – | 1.323 (3) |
Bi1—X5—Bi1i | 97.40 (3) | 95.335 (12) | 97.096 (16) |
Symmetry code (i) for (2) and (3): -x+1, -y+1, -z; for (4): -x+1/2, -y+3/2, -z. |
(5) (X = I) | (6) (X = Br) | |
Bi1—X1 | 2.9432 (3) | 2.7079 (4) |
Bi1—X2 | 2.9187 (3) | 2.6431 (4) |
Bi1—X3 | 3.1003 (3) | 2.8846 (4) |
Bi1—X3i | 3.3348 (3) | 3.1822 (4) |
Bi1—X4 | 3.0660 (3) | 2.8787 (4) |
Bi1—X4ii | 3.2248 (3) | 3.0620 (4) |
N2—C1 | 1.342 (5) | – |
N3—C5 | 1.325 (6) | – |
N2—C3 | – | 1.326 (6) |
Bi1—X3—Bi1i | 94.738 (7) | 92.407 (11) |
Bi1—X4—Bi1ii | 92.869 (8) | 95.064 (11) |
Symmetry codes for (5): (i) -x+1, -y+2, -z+1; (ii) -x+1, -y+1, -z+1; for (6): (i) x, -y+1/2, z-1/2; (ii) x, -y+1/2, z+1/2. |
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