Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616010615/yp3123sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229616010615/yp3123BiTmCl2sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229616010615/yp3123BiTmClm-Cl2sup3.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229616010615/yp3123sup4.pdf |
CCDC references: 1488897; 1488896
For both compounds, data collection: CrystalClear-SM Expert (Rigaku, 2013); cell refinement: CrystalClear-SM Expert (Rigaku, 2013); data reduction: CrystalClear-SM Expert (Rigaku, 2013). Program(s) used to solve structure: SIR2011 (Burla et al., 2012) for BiTmCl2; Il Milione (Burla et al., 2007) for BiTmClm-Cl2. For both compounds, program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: CrystalStructure (Rigaku, 2015); software used to prepare material for publication: CrystalStructure (Rigaku, 2015).
[Bi(C21H34BN6S3)Cl2(CH4O)] | Z = 2 |
Mr = 789.46 | F(000) = 780.00 |
Triclinic, P1 | Dx = 1.697 Mg m−3 |
a = 10.2899 (5) Å | Mo Kα radiation, λ = 0.71075 Å |
b = 10.6653 (4) Å | Cell parameters from 6399 reflections |
c = 15.9818 (10) Å | θ = 3.0–27.5° |
α = 72.157 (6)° | µ = 6.10 mm−1 |
β = 83.838 (8)° | T = 179 K |
γ = 67.742 (7)° | Block, orange |
V = 1545.08 (16) Å3 | 0.24 × 0.16 × 0.07 mm |
Rigaku XtaLAB P200 diffractometer | 6768 reflections with F2 > 2.0σ(F2) |
Detector resolution: 5.814 pixels mm-1 | Rint = 0.037 |
ω scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: numerical (NUMABS; Rigaku, 1999) | h = −13→13 |
Tmin = 0.465, Tmax = 0.653 | k = −13→13 |
51186 measured reflections | l = −20→20 |
7083 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.012 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.032 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0201P)2] where P = (Fo2 + 2Fc2)/3 |
7083 reflections | (Δ/σ)max = 0.008 |
327 parameters | Δρmax = 1.03 e Å−3 |
0 restraints | Δρmin = −0.66 e Å−3 |
Primary atom site location: structure-invariant direct methods |
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. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 sigma(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
Bi1 | 0.36354 (2) | 1.04501 (2) | 0.67383 (2) | 0.01603 (2) | |
Cl1 | 0.25103 (5) | 1.26183 (4) | 0.53006 (3) | 0.02523 (8) | |
Cl2 | 0.50213 (4) | 1.17929 (5) | 0.73128 (3) | 0.02968 (9) | |
S1 | 0.20113 (4) | 1.14394 (4) | 0.79687 (3) | 0.01864 (8) | |
S2 | 0.45474 (4) | 0.76840 (4) | 0.79180 (2) | 0.02165 (8) | |
S3 | 0.15003 (4) | 0.98696 (4) | 0.62743 (2) | 0.01790 (7) | |
O1 | 0.62244 (15) | 0.89575 (17) | 0.61046 (10) | 0.0438 (4) | |
H1D | 0.6395 | 0.8542 | 0.5713 | 0.053* | |
N1 | −0.08146 (13) | 1.24077 (14) | 0.75734 (9) | 0.0191 (3) | |
N2 | 0.01419 (13) | 1.00946 (14) | 0.81002 (9) | 0.0187 (3) | |
N3 | 0.43620 (14) | 0.78152 (14) | 0.96219 (9) | 0.0214 (3) | |
N4 | 0.23275 (15) | 0.82784 (14) | 0.90396 (8) | 0.0202 (3) | |
N5 | 0.22948 (14) | 0.69860 (13) | 0.65939 (9) | 0.0188 (3) | |
N6 | 0.15131 (14) | 0.77211 (14) | 0.77630 (8) | 0.0198 (3) | |
C1 | −0.0224 (2) | 1.4371 (2) | 0.65160 (12) | 0.0338 (4) | |
H1A | −0.0408 | 1.5388 | 0.6351 | 0.041* | |
H1B | 0.0776 | 1.3839 | 0.6658 | 0.041* | |
H1C | −0.0477 | 1.4138 | 0.6024 | 0.041* | |
C2 | −0.2653 (2) | 1.4796 (2) | 0.70769 (15) | 0.0388 (5) | |
H2A | −0.2849 | 1.5815 | 0.6909 | 0.047* | |
H2B | −0.2884 | 1.4551 | 0.6584 | 0.047* | |
H2C | −0.3224 | 1.4546 | 0.7585 | 0.047* | |
C3 | −0.0764 (2) | 1.4329 (2) | 0.81079 (13) | 0.0340 (4) | |
H3A | −0.0940 | 1.5343 | 0.7954 | 0.041* | |
H3B | −0.1363 | 1.4082 | 0.8600 | 0.041* | |
H3C | 0.0224 | 1.3786 | 0.8278 | 0.041* | |
C4 | −0.10966 (17) | 1.39816 (17) | 0.73153 (11) | 0.0243 (3) | |
C5 | 0.04038 (15) | 1.13061 (16) | 0.78764 (10) | 0.0166 (3) | |
C6 | −0.18439 (17) | 1.18594 (18) | 0.75890 (11) | 0.0226 (3) | |
H6 | −0.2794 | 1.2387 | 0.7404 | 0.027* | |
C7 | −0.12563 (17) | 1.04496 (18) | 0.79122 (11) | 0.0228 (3) | |
H7 | −0.1722 | 0.9803 | 0.7998 | 0.027* | |
C8 | 0.6598 (2) | 0.57980 (19) | 0.97319 (12) | 0.0316 (4) | |
H8A | 0.7612 | 0.5455 | 0.9837 | 0.038* | |
H8B | 0.6190 | 0.5192 | 1.0177 | 0.038* | |
H8C | 0.6429 | 0.5773 | 0.9146 | 0.038* | |
C9 | 0.6141 (2) | 0.7329 (2) | 1.07119 (13) | 0.0374 (5) | |
H9A | 0.7149 | 0.7009 | 1.0828 | 0.045* | |
H9B | 0.5673 | 0.8292 | 1.0762 | 0.045* | |
H9C | 0.5745 | 0.6693 | 1.1140 | 0.045* | |
C10 | 0.6543 (2) | 0.8316 (2) | 0.91306 (14) | 0.0427 (5) | |
H10A | 0.7553 | 0.7982 | 0.9245 | 0.051* | |
H10B | 0.6391 | 0.8335 | 0.8531 | 0.051* | |
H10C | 0.6086 | 0.9272 | 0.9195 | 0.051* | |
C11 | 0.59183 (18) | 0.73193 (18) | 0.97865 (11) | 0.0243 (3) | |
C12 | 0.37182 (17) | 0.79315 (16) | 0.88797 (10) | 0.0187 (3) | |
C13 | 0.33391 (19) | 0.81150 (19) | 1.02439 (11) | 0.0278 (4) | |
H13 | 0.3487 | 0.8122 | 1.0819 | 0.033* | |
C14 | 0.20998 (19) | 0.83945 (19) | 0.98888 (10) | 0.0267 (4) | |
H14 | 0.1216 | 0.8632 | 1.0171 | 0.032* | |
C15 | 0.14735 (19) | 0.7795 (2) | 0.50545 (11) | 0.0292 (4) | |
H15A | 0.1754 | 0.7766 | 0.4453 | 0.035* | |
H15B | 0.0738 | 0.7396 | 0.5242 | 0.035* | |
H15C | 0.1114 | 0.8778 | 0.5074 | 0.035* | |
C16 | 0.39551 (19) | 0.7470 (2) | 0.54034 (12) | 0.0288 (4) | |
H16A | 0.4245 | 0.7434 | 0.4804 | 0.035* | |
H16B | 0.3646 | 0.8448 | 0.5427 | 0.035* | |
H16C | 0.4749 | 0.6871 | 0.5809 | 0.035* | |
C17 | 0.3252 (2) | 0.53949 (19) | 0.56530 (13) | 0.0338 (4) | |
H17A | 0.3546 | 0.5344 | 0.5057 | 0.041* | |
H17B | 0.4049 | 0.4820 | 0.6060 | 0.041* | |
H17C | 0.2488 | 0.5035 | 0.5832 | 0.041* | |
C18 | 0.27423 (17) | 0.69314 (17) | 0.56696 (10) | 0.0214 (3) | |
C19 | 0.17947 (16) | 0.81433 (16) | 0.68941 (10) | 0.0171 (3) | |
C20 | 0.23340 (19) | 0.58114 (17) | 0.72914 (11) | 0.0258 (4) | |
H20 | 0.2646 | 0.4861 | 0.7271 | 0.031* | |
C21 | 0.18492 (19) | 0.62702 (17) | 0.79991 (11) | 0.0264 (4) | |
H21 | 0.1752 | 0.5694 | 0.8570 | 0.032* | |
C22 | 0.7500 (2) | 0.8917 (2) | 0.63949 (15) | 0.0427 (5) | |
H22A | 0.7306 | 0.9713 | 0.6633 | 0.051* | |
H22B | 0.8142 | 0.8984 | 0.5899 | 0.051* | |
H22C | 0.7931 | 0.8026 | 0.6853 | 0.051* | |
B1 | 0.1064 (2) | 0.8501 (2) | 0.84775 (12) | 0.0208 (4) | |
H1 | 0.0452 | 0.8058 | 0.8891 | 0.025* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Bi1 | 0.01464 (3) | 0.01767 (3) | 0.01733 (3) | −0.00662 (2) | 0.00094 (2) | −0.00655 (2) |
Cl1 | 0.0344 (2) | 0.02018 (19) | 0.02140 (18) | −0.01082 (17) | 0.00152 (16) | −0.00566 (15) |
Cl2 | 0.0225 (2) | 0.0394 (2) | 0.0369 (2) | −0.01774 (19) | 0.00175 (17) | −0.01666 (19) |
S1 | 0.01422 (17) | 0.0227 (2) | 0.02320 (18) | −0.00741 (15) | 0.00018 (14) | −0.01156 (15) |
S2 | 0.02088 (19) | 0.0249 (2) | 0.01456 (16) | −0.00174 (16) | −0.00040 (14) | −0.00753 (15) |
S3 | 0.02191 (19) | 0.01311 (17) | 0.01865 (17) | −0.00623 (15) | −0.00488 (14) | −0.00307 (14) |
O1 | 0.0377 (8) | 0.0580 (10) | 0.0466 (9) | −0.0171 (7) | 0.0138 (7) | −0.0353 (8) |
N1 | 0.0140 (6) | 0.0211 (7) | 0.0227 (6) | −0.0048 (5) | 0.0013 (5) | −0.0097 (5) |
N2 | 0.0154 (6) | 0.0216 (7) | 0.0210 (6) | −0.0076 (5) | 0.0014 (5) | −0.0082 (5) |
N3 | 0.0235 (7) | 0.0213 (7) | 0.0170 (6) | −0.0028 (6) | −0.0029 (5) | −0.0079 (5) |
N4 | 0.0239 (7) | 0.0206 (7) | 0.0143 (6) | −0.0059 (6) | 0.0016 (5) | −0.0059 (5) |
N5 | 0.0224 (7) | 0.0144 (6) | 0.0207 (6) | −0.0071 (5) | −0.0036 (5) | −0.0048 (5) |
N6 | 0.0248 (7) | 0.0160 (6) | 0.0191 (6) | −0.0087 (6) | −0.0022 (5) | −0.0031 (5) |
C1 | 0.0318 (10) | 0.0274 (10) | 0.0328 (10) | −0.0069 (8) | 0.0053 (8) | −0.0022 (8) |
C2 | 0.0221 (9) | 0.0264 (10) | 0.0568 (13) | 0.0016 (8) | 0.0000 (9) | −0.0098 (9) |
C3 | 0.0388 (11) | 0.0251 (9) | 0.0414 (11) | −0.0087 (8) | 0.0064 (8) | −0.0201 (8) |
C4 | 0.0208 (8) | 0.0193 (8) | 0.0307 (9) | −0.0041 (7) | 0.0037 (7) | −0.0094 (7) |
C5 | 0.0138 (7) | 0.0198 (8) | 0.0185 (7) | −0.0055 (6) | 0.0017 (5) | −0.0099 (6) |
C6 | 0.0134 (7) | 0.0298 (9) | 0.0263 (8) | −0.0078 (7) | 0.0015 (6) | −0.0110 (7) |
C7 | 0.0168 (8) | 0.0305 (9) | 0.0272 (8) | −0.0126 (7) | 0.0032 (6) | −0.0126 (7) |
C8 | 0.0298 (10) | 0.0283 (10) | 0.0304 (9) | 0.0019 (8) | −0.0097 (7) | −0.0124 (8) |
C9 | 0.0402 (11) | 0.0391 (11) | 0.0317 (10) | −0.0031 (9) | −0.0153 (8) | −0.0175 (9) |
C10 | 0.0388 (11) | 0.0449 (12) | 0.0423 (11) | −0.0219 (10) | −0.0124 (9) | 0.0028 (10) |
C11 | 0.0248 (8) | 0.0240 (9) | 0.0224 (8) | −0.0049 (7) | −0.0080 (6) | −0.0067 (7) |
C12 | 0.0225 (8) | 0.0150 (7) | 0.0152 (7) | −0.0031 (6) | −0.0017 (6) | −0.0040 (6) |
C13 | 0.0345 (10) | 0.0299 (9) | 0.0149 (7) | −0.0050 (8) | 0.0008 (7) | −0.0095 (7) |
C14 | 0.0298 (9) | 0.0299 (9) | 0.0161 (7) | −0.0060 (8) | 0.0058 (6) | −0.0087 (7) |
C15 | 0.0316 (9) | 0.0337 (10) | 0.0250 (8) | −0.0094 (8) | −0.0067 (7) | −0.0129 (7) |
C16 | 0.0241 (9) | 0.0283 (9) | 0.0361 (10) | −0.0099 (8) | 0.0037 (7) | −0.0128 (8) |
C17 | 0.0451 (11) | 0.0225 (9) | 0.0370 (10) | −0.0115 (8) | 0.0067 (9) | −0.0160 (8) |
C18 | 0.0243 (8) | 0.0195 (8) | 0.0225 (8) | −0.0071 (7) | −0.0011 (6) | −0.0097 (6) |
C19 | 0.0174 (7) | 0.0151 (7) | 0.0198 (7) | −0.0066 (6) | −0.0038 (6) | −0.0043 (6) |
C20 | 0.0352 (9) | 0.0149 (8) | 0.0271 (8) | −0.0102 (7) | −0.0042 (7) | −0.0029 (6) |
C21 | 0.0383 (10) | 0.0174 (8) | 0.0236 (8) | −0.0131 (7) | −0.0036 (7) | −0.0008 (6) |
C22 | 0.0408 (12) | 0.0457 (13) | 0.0449 (12) | −0.0117 (10) | 0.0046 (9) | −0.0241 (10) |
B1 | 0.0218 (9) | 0.0207 (9) | 0.0212 (8) | −0.0092 (8) | 0.0022 (7) | −0.0066 (7) |
Bi1—S1 | 2.6463 (5) | C3—H3B | 0.9800 |
Bi1—Cl1 | 2.6933 (5) | C3—H3C | 0.9800 |
Bi1—S3 | 2.7242 (4) | C6—C7 | 1.340 (2) |
Bi1—Cl2 | 2.7499 (4) | C6—H6 | 0.9500 |
Bi1—S2 | 2.8307 (5) | C7—H7 | 0.9500 |
Bi1—O1 | 2.8023 (14) | C8—C11 | 1.531 (2) |
S1—C5 | 1.7381 (15) | C8—H8A | 0.9800 |
S2—C12 | 1.7193 (16) | C8—H8B | 0.9800 |
S3—C19 | 1.7283 (15) | C8—H8C | 0.9800 |
O1—C22 | 1.419 (3) | C9—C11 | 1.524 (2) |
O1—H1D | 0.8400 | C9—H9A | 0.9800 |
N1—C5 | 1.361 (2) | C9—H9B | 0.9800 |
N1—C6 | 1.3852 (19) | C9—H9C | 0.9800 |
N1—C4 | 1.518 (2) | C10—C11 | 1.527 (3) |
N2—C5 | 1.3528 (19) | C10—H10A | 0.9800 |
N2—C7 | 1.383 (2) | C10—H10B | 0.9800 |
N2—B1 | 1.558 (2) | C10—H10C | 0.9800 |
N3—C12 | 1.3702 (19) | C13—C14 | 1.342 (3) |
N3—C13 | 1.383 (2) | C13—H13 | 0.9500 |
N3—C11 | 1.509 (2) | C14—H14 | 0.9500 |
N4—C12 | 1.352 (2) | C15—C18 | 1.526 (2) |
N4—C14 | 1.387 (2) | C15—H15A | 0.9800 |
N4—B1 | 1.562 (2) | C15—H15B | 0.9800 |
N5—C19 | 1.359 (2) | C15—H15C | 0.9800 |
N5—C20 | 1.389 (2) | C16—C18 | 1.532 (2) |
N5—C18 | 1.511 (2) | C16—H16A | 0.9800 |
N6—C19 | 1.3580 (19) | C16—H16B | 0.9800 |
N6—C21 | 1.386 (2) | C16—H16C | 0.9800 |
N6—B1 | 1.545 (2) | C17—C18 | 1.528 (2) |
C1—C4 | 1.524 (2) | C17—H17A | 0.9800 |
C1—H1A | 0.9800 | C17—H17B | 0.9800 |
C1—H1B | 0.9800 | C17—H17C | 0.9800 |
C1—H1C | 0.9800 | C20—C21 | 1.342 (2) |
C2—C4 | 1.529 (2) | C20—H20 | 0.9500 |
C2—H2A | 0.9800 | C21—H21 | 0.9500 |
C2—H2B | 0.9800 | C22—H22A | 0.9800 |
C2—H2C | 0.9800 | C22—H22B | 0.9800 |
C3—C4 | 1.528 (2) | C22—H22C | 0.9800 |
C3—H3A | 0.9800 | B1—H1 | 1.0000 |
S1—Bi1—Cl1 | 100.115 (14) | H8A—C8—H8C | 109.5 |
S1—Bi1—S3 | 88.960 (13) | H8B—C8—H8C | 109.5 |
Cl1—Bi1—S3 | 76.546 (13) | C11—C9—H9A | 109.5 |
S1—Bi1—Cl2 | 74.926 (13) | C11—C9—H9B | 109.5 |
Cl1—Bi1—Cl2 | 95.046 (14) | H9A—C9—H9B | 109.5 |
S3—Bi1—Cl2 | 160.381 (14) | C11—C9—H9C | 109.5 |
S1—Bi1—S2 | 90.300 (14) | H9A—C9—H9C | 109.5 |
Cl1—Bi1—S2 | 160.302 (13) | H9B—C9—H9C | 109.5 |
S3—Bi1—S2 | 87.065 (14) | C11—C10—H10A | 109.5 |
Cl2—Bi1—S2 | 103.836 (14) | C11—C10—H10B | 109.5 |
S1—Bi1—O1 | 152.76 (4) | H10A—C10—H10B | 109.5 |
S2—Bi1—O1 | 74.07 (3) | C11—C10—H10C | 109.5 |
S3—Bi1—O1 | 111.80 (4) | H10A—C10—H10C | 109.5 |
Cl1—Bi1—O1 | 101.73 (3) | H10B—C10—H10C | 109.5 |
Cl2—Bi1—O1 | 87.10 (4) | N3—C11—C9 | 108.59 (14) |
C5—S1—Bi1 | 106.38 (5) | N3—C11—C10 | 110.33 (14) |
C12—S2—Bi1 | 103.20 (5) | C9—C11—C10 | 108.58 (16) |
C19—S3—Bi1 | 104.44 (5) | N3—C11—C8 | 108.13 (14) |
C22—O1—H1D | 109.5 | C9—C11—C8 | 108.76 (14) |
C5—N1—C6 | 108.00 (13) | C10—C11—C8 | 112.36 (17) |
C5—N1—C4 | 128.36 (13) | N4—C12—N3 | 107.91 (13) |
C6—N1—C4 | 123.51 (13) | N4—C12—S2 | 126.54 (12) |
C5—N2—C7 | 107.75 (13) | N3—C12—S2 | 125.54 (12) |
C5—N2—B1 | 133.83 (13) | C14—C13—N3 | 107.66 (14) |
C7—N2—B1 | 118.40 (13) | C14—C13—H13 | 126.2 |
C12—N3—C13 | 108.05 (14) | N3—C13—H13 | 126.2 |
C12—N3—C11 | 127.23 (14) | C13—C14—N4 | 108.47 (15) |
C13—N3—C11 | 124.50 (13) | C13—C14—H14 | 125.8 |
C12—N4—C14 | 107.90 (13) | N4—C14—H14 | 125.8 |
C12—N4—B1 | 132.50 (13) | C18—C15—H15A | 109.5 |
C14—N4—B1 | 119.57 (14) | C18—C15—H15B | 109.5 |
C19—N5—C20 | 108.25 (13) | H15A—C15—H15B | 109.5 |
C19—N5—C18 | 127.58 (13) | C18—C15—H15C | 109.5 |
C20—N5—C18 | 124.16 (13) | H15A—C15—H15C | 109.5 |
C19—N6—C21 | 107.34 (13) | H15B—C15—H15C | 109.5 |
C19—N6—B1 | 132.76 (13) | C18—C16—H16A | 109.5 |
C21—N6—B1 | 119.59 (13) | C18—C16—H16B | 109.5 |
C4—C1—H1A | 109.5 | H16A—C16—H16B | 109.5 |
C4—C1—H1B | 109.5 | C18—C16—H16C | 109.5 |
H1A—C1—H1B | 109.5 | H16A—C16—H16C | 109.5 |
C4—C1—H1C | 109.5 | H16B—C16—H16C | 109.5 |
H1A—C1—H1C | 109.5 | C18—C17—H17A | 109.5 |
H1B—C1—H1C | 109.5 | C18—C17—H17B | 109.5 |
C4—C2—H2A | 109.5 | H17A—C17—H17B | 109.5 |
C4—C2—H2B | 109.5 | C18—C17—H17C | 109.5 |
H2A—C2—H2B | 109.5 | H17A—C17—H17C | 109.5 |
C4—C2—H2C | 109.5 | H17B—C17—H17C | 109.5 |
H2A—C2—H2C | 109.5 | N5—C18—C15 | 108.87 (13) |
H2B—C2—H2C | 109.5 | N5—C18—C17 | 108.59 (13) |
C4—C3—H3A | 109.5 | C15—C18—C17 | 108.52 (14) |
C4—C3—H3B | 109.5 | N5—C18—C16 | 109.45 (13) |
H3A—C3—H3B | 109.5 | C15—C18—C16 | 112.53 (14) |
C4—C3—H3C | 109.5 | C17—C18—C16 | 108.80 (15) |
H3A—C3—H3C | 109.5 | N6—C19—N5 | 108.29 (13) |
H3B—C3—H3C | 109.5 | N6—C19—S3 | 125.46 (12) |
N1—C4—C1 | 109.70 (14) | N5—C19—S3 | 126.22 (12) |
N1—C4—C3 | 108.27 (14) | C21—C20—N5 | 107.17 (14) |
C1—C4—C3 | 112.34 (15) | C21—C20—H20 | 126.4 |
N1—C4—C2 | 108.68 (14) | N5—C20—H20 | 126.4 |
C1—C4—C2 | 108.85 (15) | C20—C21—N6 | 108.95 (14) |
C3—C4—C2 | 108.92 (15) | C20—C21—H21 | 125.5 |
N2—C5—N1 | 108.14 (13) | N6—C21—H21 | 125.5 |
N2—C5—S1 | 126.07 (12) | O1—C22—H22A | 109.5 |
N1—C5—S1 | 125.79 (12) | O1—C22—H22B | 109.5 |
C7—C6—N1 | 107.55 (14) | H22A—C22—H22B | 109.5 |
C7—C6—H6 | 126.2 | O1—C22—H22C | 109.5 |
N1—C6—H6 | 126.2 | H22A—C22—H22C | 109.5 |
C6—C7—N2 | 108.53 (14) | H22B—C22—H22C | 109.5 |
C6—C7—H7 | 125.7 | N6—B1—N2 | 112.52 (13) |
N2—C7—H7 | 125.7 | N6—B1—N4 | 112.92 (14) |
C11—C8—H8A | 109.5 | N2—B1—N4 | 112.23 (13) |
C11—C8—H8B | 109.5 | N6—B1—H1 | 106.2 |
H8A—C8—H8B | 109.5 | N2—B1—H1 | 106.2 |
C11—C8—H8C | 109.5 | N4—B1—H1 | 106.2 |
C5—N1—C4—C1 | 65.0 (2) | C11—N3—C13—C14 | −174.35 (15) |
C6—N1—C4—C1 | −119.63 (17) | N3—C13—C14—N4 | −0.2 (2) |
C5—N1—C4—C3 | −57.9 (2) | C12—N4—C14—C13 | −0.3 (2) |
C6—N1—C4—C3 | 117.46 (17) | B1—N4—C14—C13 | 177.98 (15) |
C5—N1—C4—C2 | −176.10 (16) | C19—N5—C18—C15 | −62.95 (19) |
C6—N1—C4—C2 | −0.7 (2) | C20—N5—C18—C15 | 116.96 (17) |
C7—N2—C5—N1 | 1.47 (17) | C19—N5—C18—C17 | 179.07 (15) |
B1—N2—C5—N1 | 179.71 (15) | C20—N5—C18—C17 | −1.0 (2) |
C7—N2—C5—S1 | −179.10 (12) | C19—N5—C18—C16 | 60.4 (2) |
B1—N2—C5—S1 | −0.9 (2) | C20—N5—C18—C16 | −119.66 (16) |
C6—N1—C5—N2 | −1.59 (17) | C21—N6—C19—N5 | −0.02 (17) |
C4—N1—C5—N2 | 174.36 (14) | B1—N6—C19—N5 | 173.38 (15) |
C6—N1—C5—S1 | 178.98 (12) | C21—N6—C19—S3 | 177.76 (12) |
C4—N1—C5—S1 | −5.1 (2) | B1—N6—C19—S3 | −8.8 (2) |
Bi1—S1—C5—N2 | 71.57 (14) | C20—N5—C19—N6 | −0.30 (17) |
Bi1—S1—C5—N1 | −109.10 (13) | C18—N5—C19—N6 | 179.63 (14) |
C5—N1—C6—C7 | 1.10 (18) | C20—N5—C19—S3 | −178.05 (12) |
C4—N1—C6—C7 | −175.09 (14) | C18—N5—C19—S3 | 1.9 (2) |
N1—C6—C7—N2 | −0.20 (19) | Bi1—S3—C19—N6 | 76.69 (13) |
C5—N2—C7—C6 | −0.78 (18) | Bi1—S3—C19—N5 | −105.93 (13) |
B1—N2—C7—C6 | −179.34 (14) | C19—N5—C20—C21 | 0.51 (19) |
C12—N3—C11—C9 | −178.53 (16) | C18—N5—C20—C21 | −179.42 (14) |
C13—N3—C11—C9 | −4.6 (2) | N5—C20—C21—N6 | −0.5 (2) |
C12—N3—C11—C10 | 62.6 (2) | C19—N6—C21—C20 | 0.34 (19) |
C13—N3—C11—C10 | −123.47 (18) | B1—N6—C21—C20 | −174.09 (15) |
C12—N3—C11—C8 | −60.7 (2) | C19—N6—B1—N2 | 31.8 (2) |
C13—N3—C11—C8 | 113.28 (18) | C21—N6—B1—N2 | −155.42 (14) |
C14—N4—C12—N3 | 0.63 (18) | C19—N6—B1—N4 | −96.48 (19) |
B1—N4—C12—N3 | −177.31 (15) | C21—N6—B1—N4 | 76.27 (18) |
C14—N4—C12—S2 | −179.10 (13) | C5—N2—B1—N6 | −100.67 (19) |
B1—N4—C12—S2 | 3.0 (3) | C7—N2—B1—N6 | 77.43 (17) |
C13—N3—C12—N4 | −0.75 (18) | C5—N2—B1—N4 | 28.0 (2) |
C11—N3—C12—N4 | 174.00 (14) | C7—N2—B1—N4 | −153.90 (13) |
C13—N3—C12—S2 | 178.99 (12) | C12—N4—B1—N6 | 23.5 (2) |
C11—N3—C12—S2 | −6.3 (2) | C14—N4—B1—N6 | −154.27 (14) |
Bi1—S2—C12—N4 | 70.01 (14) | C12—N4—B1—N2 | −104.98 (19) |
Bi1—S2—C12—N3 | −109.68 (13) | C14—N4—B1—N2 | 77.27 (18) |
C12—N3—C13—C14 | 0.58 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1D···Cl1i | 0.84 | 2.28 | 3.0969 (18) | 164 |
Symmetry code: (i) −x+1, −y+2, −z+1. |
[Bi2(C21H34BN6S3)2Cl4] | Z = 1 |
Mr = 1514.83 | F(000) = 744.00 |
Triclinic, P1 | Dx = 1.759 Mg m−3 |
a = 10.8009 (11) Å | Mo Kα radiation, λ = 0.71075 Å |
b = 11.3698 (14) Å | Cell parameters from 6052 reflections |
c = 11.8690 (13) Å | θ = 3.0–27.5° |
α = 95.125 (4)° | µ = 6.58 mm−1 |
β = 91.947 (4)° | T = 179 K |
γ = 99.549 (3)° | Block, orange |
V = 1429.9 (3) Å3 | 0.23 × 0.15 × 0.15 mm |
Rigaku XtaLAB P200 diffractometer | 5816 reflections with F2 > 2.0σ(F2) |
Detector resolution: 5.814 pixels mm-1 | Rint = 0.034 |
ω scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: numerical (NUMABS; Rigaku, 1999) | h = −14→14 |
Tmin = 0.270, Tmax = 0.373 | k = −14→14 |
39709 measured reflections | l = −14→15 |
6115 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.013 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.033 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.019P)2] where P = (Fo2 + 2Fc2)/3 |
6115 reflections | (Δ/σ)max = 0.001 |
307 parameters | Δρmax = 0.59 e Å−3 |
0 restraints | Δρmin = −0.85 e Å−3 |
Primary atom site location: structure-invariant direct methods |
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. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 sigma(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
Bi1 | 0.39969 (2) | 0.41301 (2) | 0.85362 (2) | 0.01774 (3) | |
Cl1 | 0.37944 (5) | 0.61914 (5) | 1.01595 (4) | 0.03186 (11) | |
Cl2 | 0.54822 (4) | 0.56134 (4) | 0.74438 (5) | 0.02943 (11) | |
S1 | 0.18081 (4) | 0.26572 (4) | 0.93598 (4) | 0.02185 (10) | |
S2 | 0.45110 (4) | 0.20689 (4) | 0.74473 (4) | 0.01891 (9) | |
S3 | 0.24933 (4) | 0.44487 (4) | 0.67720 (4) | 0.02081 (10) | |
N1 | 0.22072 (14) | 0.03193 (13) | 0.93270 (12) | 0.0190 (3) | |
N2 | 0.16688 (14) | 0.08266 (13) | 0.76597 (12) | 0.0181 (3) | |
N3 | 0.43753 (14) | 0.20501 (13) | 0.51162 (12) | 0.0184 (3) | |
N4 | 0.25221 (14) | 0.17310 (13) | 0.58613 (12) | 0.0190 (3) | |
N5 | 0.00025 (13) | 0.41876 (13) | 0.73377 (13) | 0.0206 (3) | |
N6 | 0.06462 (13) | 0.24855 (13) | 0.68614 (12) | 0.0189 (3) | |
C1 | 0.3749 (2) | 0.1261 (2) | 1.08680 (19) | 0.0363 (5) | |
H1A | 0.3979 | 0.1279 | 1.1676 | 0.044* | |
H1B | 0.4434 | 0.1038 | 1.0420 | 0.044* | |
H1C | 0.3598 | 0.2055 | 1.0700 | 0.044* | |
C2 | 0.1451 (2) | 0.06199 (19) | 1.12597 (17) | 0.0303 (5) | |
H2A | 0.1674 | 0.0635 | 1.2069 | 0.036* | |
H2B | 0.1258 | 0.1402 | 1.1099 | 0.036* | |
H2C | 0.0713 | 0.0000 | 1.1053 | 0.036* | |
C3 | 0.2806 (2) | −0.0901 (2) | 1.08051 (18) | 0.0344 (5) | |
H3A | 0.3033 | −0.0900 | 1.1612 | 0.041* | |
H3B | 0.2047 | −0.1495 | 1.0601 | 0.041* | |
H3C | 0.3497 | −0.1103 | 1.0354 | 0.041* | |
C4 | 0.25550 (17) | 0.03418 (17) | 1.05699 (15) | 0.0231 (4) | |
C5 | 0.19061 (16) | 0.12427 (15) | 0.87656 (15) | 0.0174 (4) | |
C6 | 0.21619 (19) | −0.06658 (16) | 0.85467 (16) | 0.0250 (4) | |
H6 | 0.2336 | −0.1429 | 0.8703 | 0.030* | |
C7 | 0.18299 (18) | −0.03572 (16) | 0.75342 (16) | 0.0237 (4) | |
H7 | 0.1723 | −0.0865 | 0.6845 | 0.028* | |
C8 | 0.6337 (2) | 0.35132 (18) | 0.54280 (18) | 0.0300 (5) | |
H8A | 0.7244 | 0.3657 | 0.5323 | 0.036* | |
H8B | 0.5942 | 0.4089 | 0.5036 | 0.036* | |
H8C | 0.6187 | 0.3610 | 0.6238 | 0.036* | |
C9 | 0.63882 (18) | 0.13017 (18) | 0.54876 (17) | 0.0268 (4) | |
H9A | 0.7292 | 0.1440 | 0.5368 | 0.032* | |
H9B | 0.6254 | 0.1357 | 0.6302 | 0.032* | |
H9C | 0.6010 | 0.0502 | 0.5142 | 0.032* | |
C10 | 0.59799 (19) | 0.21018 (19) | 0.36664 (16) | 0.0287 (4) | |
H10A | 0.6883 | 0.2227 | 0.3543 | 0.034* | |
H10B | 0.5595 | 0.1293 | 0.3351 | 0.034* | |
H10C | 0.5591 | 0.2693 | 0.3291 | 0.034* | |
C11 | 0.57765 (17) | 0.22470 (17) | 0.49425 (15) | 0.0216 (4) | |
C12 | 0.37782 (16) | 0.19445 (15) | 0.61077 (14) | 0.0170 (3) | |
C13 | 0.34632 (18) | 0.19420 (18) | 0.42468 (16) | 0.0241 (4) | |
H13 | 0.3609 | 0.1999 | 0.3467 | 0.029* | |
C14 | 0.23349 (18) | 0.17415 (18) | 0.47038 (15) | 0.0243 (4) | |
H14 | 0.1543 | 0.1627 | 0.4300 | 0.029* | |
C15 | 0.0832 (2) | 0.6027 (2) | 0.8588 (2) | 0.0394 (5) | |
H15A | 0.0791 | 0.6879 | 0.8752 | 0.047* | |
H15B | 0.0593 | 0.5604 | 0.9252 | 0.047* | |
H15C | 0.1691 | 0.5935 | 0.8405 | 0.047* | |
C16 | 0.0232 (2) | 0.61294 (19) | 0.6516 (2) | 0.0388 (5) | |
H16A | 0.0189 | 0.6983 | 0.6667 | 0.047* | |
H16B | 0.1079 | 0.6038 | 0.6294 | 0.047* | |
H16C | −0.0380 | 0.5771 | 0.5901 | 0.047* | |
C17 | −0.1409 (2) | 0.5614 (2) | 0.7884 (2) | 0.0424 (6) | |
H17A | −0.1470 | 0.6462 | 0.8046 | 0.051* | |
H17B | −0.1991 | 0.5261 | 0.7245 | 0.051* | |
H17C | −0.1626 | 0.5191 | 0.8553 | 0.051* | |
C18 | −0.00674 (17) | 0.55006 (17) | 0.75832 (18) | 0.0262 (4) | |
C19 | 0.10116 (16) | 0.36878 (16) | 0.70073 (15) | 0.0182 (4) | |
C20 | −0.09990 (17) | 0.32700 (18) | 0.74195 (17) | 0.0263 (4) | |
H20 | −0.1817 | 0.3358 | 0.7646 | 0.032* | |
C21 | −0.06013 (17) | 0.22343 (17) | 0.71200 (17) | 0.0250 (4) | |
H21 | −0.1095 | 0.1458 | 0.7091 | 0.030* | |
B1 | 0.13545 (19) | 0.14250 (19) | 0.65828 (17) | 0.0199 (4) | |
H1 | 0.0750 | 0.0805 | 0.6102 | 0.024* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Bi1 | 0.01588 (4) | 0.01547 (4) | 0.02072 (4) | 0.00196 (3) | −0.00091 (3) | −0.00250 (3) |
Cl1 | 0.0333 (3) | 0.0311 (3) | 0.0322 (3) | 0.0143 (2) | −0.0045 (2) | −0.0054 (2) |
Cl2 | 0.0192 (2) | 0.0237 (2) | 0.0458 (3) | 0.00227 (18) | 0.0058 (2) | 0.0070 (2) |
S1 | 0.0284 (2) | 0.0156 (2) | 0.0213 (2) | 0.00477 (18) | 0.00527 (19) | −0.00240 (18) |
S2 | 0.0203 (2) | 0.0211 (2) | 0.0155 (2) | 0.00582 (18) | −0.00146 (17) | −0.00098 (17) |
S3 | 0.0129 (2) | 0.0214 (2) | 0.0285 (2) | 0.00180 (17) | 0.00229 (18) | 0.00610 (19) |
N1 | 0.0211 (8) | 0.0175 (8) | 0.0191 (8) | 0.0043 (6) | 0.0044 (6) | 0.0016 (6) |
N2 | 0.0201 (8) | 0.0158 (7) | 0.0181 (8) | 0.0032 (6) | 0.0033 (6) | −0.0007 (6) |
N3 | 0.0189 (7) | 0.0209 (8) | 0.0164 (7) | 0.0070 (6) | 0.0012 (6) | 0.0006 (6) |
N4 | 0.0192 (7) | 0.0214 (8) | 0.0167 (7) | 0.0060 (6) | −0.0002 (6) | −0.0003 (6) |
N5 | 0.0128 (7) | 0.0205 (8) | 0.0280 (8) | 0.0025 (6) | 0.0004 (6) | 0.0003 (6) |
N6 | 0.0147 (7) | 0.0192 (8) | 0.0225 (8) | 0.0020 (6) | 0.0007 (6) | 0.0026 (6) |
C1 | 0.0299 (11) | 0.0471 (14) | 0.0296 (12) | −0.0004 (10) | −0.0033 (9) | 0.0063 (10) |
C2 | 0.0334 (11) | 0.0360 (12) | 0.0245 (10) | 0.0101 (9) | 0.0109 (9) | 0.0074 (9) |
C3 | 0.0416 (12) | 0.0369 (12) | 0.0303 (11) | 0.0172 (10) | 0.0049 (9) | 0.0126 (9) |
C4 | 0.0243 (10) | 0.0261 (10) | 0.0198 (9) | 0.0057 (8) | 0.0026 (8) | 0.0047 (8) |
C5 | 0.0156 (8) | 0.0153 (9) | 0.0208 (9) | 0.0011 (7) | 0.0045 (7) | 0.0003 (7) |
C6 | 0.0319 (11) | 0.0150 (9) | 0.0292 (11) | 0.0067 (8) | 0.0057 (8) | 0.0007 (8) |
C7 | 0.0293 (10) | 0.0159 (9) | 0.0249 (10) | 0.0033 (8) | 0.0057 (8) | −0.0045 (8) |
C8 | 0.0295 (11) | 0.0245 (10) | 0.0340 (12) | −0.0007 (8) | 0.0105 (9) | −0.0006 (9) |
C9 | 0.0199 (9) | 0.0291 (11) | 0.0329 (11) | 0.0080 (8) | 0.0010 (8) | 0.0033 (9) |
C10 | 0.0265 (10) | 0.0378 (12) | 0.0246 (10) | 0.0134 (9) | 0.0075 (8) | 0.0013 (9) |
C11 | 0.0195 (9) | 0.0244 (10) | 0.0218 (10) | 0.0058 (8) | 0.0044 (7) | 0.0011 (8) |
C12 | 0.0191 (9) | 0.0144 (8) | 0.0177 (9) | 0.0051 (7) | 0.0002 (7) | −0.0013 (7) |
C13 | 0.0262 (10) | 0.0325 (11) | 0.0153 (9) | 0.0095 (8) | 0.0001 (8) | 0.0027 (8) |
C14 | 0.0241 (10) | 0.0336 (11) | 0.0159 (9) | 0.0091 (8) | −0.0034 (7) | −0.0001 (8) |
C15 | 0.0335 (12) | 0.0329 (12) | 0.0480 (14) | 0.0044 (10) | −0.0063 (10) | −0.0128 (10) |
C16 | 0.0380 (12) | 0.0279 (12) | 0.0550 (15) | 0.0147 (10) | 0.0028 (11) | 0.0102 (10) |
C17 | 0.0238 (11) | 0.0320 (12) | 0.0696 (17) | 0.0077 (9) | 0.0081 (11) | −0.0139 (11) |
C18 | 0.0180 (9) | 0.0203 (10) | 0.0397 (12) | 0.0050 (7) | 0.0001 (8) | −0.0035 (8) |
C19 | 0.0137 (8) | 0.0215 (9) | 0.0191 (9) | 0.0028 (7) | −0.0004 (7) | 0.0018 (7) |
C20 | 0.0122 (9) | 0.0283 (10) | 0.0377 (12) | 0.0010 (8) | 0.0043 (8) | 0.0022 (9) |
C21 | 0.0149 (9) | 0.0235 (10) | 0.0351 (11) | −0.0014 (7) | 0.0016 (8) | 0.0043 (8) |
B1 | 0.0191 (10) | 0.0196 (10) | 0.0195 (10) | 0.0015 (8) | −0.0012 (8) | −0.0015 (8) |
Bi1—Cl2 | 2.5949 (5) | C3—H3A | 0.9800 |
Bi1—S3 | 2.6931 (5) | C3—H3B | 0.9800 |
Bi1—S2 | 2.7222 (5) | C3—H3C | 0.9800 |
Bi1—Cl1i | 2.8915 (5) | C6—C7 | 1.336 (3) |
Bi1—S1 | 2.9128 (5) | C6—H6 | 0.9500 |
Bi1—Cl1 | 2.9401 (6) | C7—H7 | 0.9500 |
Cl1—Bi1i | 2.8915 (5) | C8—C11 | 1.520 (3) |
S1—C5 | 1.7188 (18) | C8—H8A | 0.9800 |
S2—C12 | 1.7354 (18) | C8—H8B | 0.9800 |
S3—C19 | 1.7326 (18) | C8—H8C | 0.9800 |
N1—C5 | 1.369 (2) | C9—C11 | 1.530 (3) |
N1—C6 | 1.381 (2) | C9—H9A | 0.9800 |
N1—C4 | 1.507 (2) | C9—H9B | 0.9800 |
N2—C5 | 1.356 (2) | C9—H9C | 0.9800 |
N2—C7 | 1.381 (2) | C10—C11 | 1.536 (3) |
N2—B1 | 1.554 (2) | C10—H10A | 0.9800 |
N3—C12 | 1.366 (2) | C10—H10B | 0.9800 |
N3—C13 | 1.385 (2) | C10—H10C | 0.9800 |
N3—C11 | 1.517 (2) | C13—C14 | 1.344 (3) |
N4—C12 | 1.355 (2) | C13—H13 | 0.9500 |
N4—C14 | 1.383 (2) | C14—H14 | 0.9500 |
N4—B1 | 1.558 (2) | C15—C18 | 1.525 (3) |
N5—C19 | 1.364 (2) | C15—H15A | 0.9800 |
N5—C20 | 1.385 (2) | C15—H15B | 0.9800 |
N5—C18 | 1.510 (2) | C15—H15C | 0.9800 |
N6—C19 | 1.352 (2) | C16—C18 | 1.528 (3) |
N6—C21 | 1.381 (2) | C16—H16A | 0.9800 |
N6—B1 | 1.549 (2) | C16—H16B | 0.9800 |
C1—C4 | 1.529 (3) | C16—H16C | 0.9800 |
C1—H1A | 0.9800 | C17—C18 | 1.527 (3) |
C1—H1B | 0.9800 | C17—H17A | 0.9800 |
C1—H1C | 0.9800 | C17—H17B | 0.9800 |
C2—C4 | 1.529 (3) | C17—H17C | 0.9800 |
C2—H2A | 0.9800 | C20—C21 | 1.342 (3) |
C2—H2B | 0.9800 | C20—H20 | 0.9500 |
C2—H2C | 0.9800 | C21—H21 | 0.9500 |
C3—C4 | 1.529 (3) | B1—H1 | 1.0000 |
Cl2—Bi1—S3 | 77.787 (16) | C11—C8—H8B | 109.5 |
Cl2—Bi1—S2 | 97.312 (17) | H8A—C8—H8B | 109.5 |
S3—Bi1—S2 | 91.074 (15) | C11—C8—H8C | 109.5 |
Cl2—Bi1—Cl1i | 87.108 (17) | H8A—C8—H8C | 109.5 |
S3—Bi1—Cl1i | 160.787 (15) | H8B—C8—H8C | 109.5 |
S2—Bi1—Cl1i | 79.020 (15) | C11—C9—H9A | 109.5 |
Cl2—Bi1—S1 | 164.283 (15) | C11—C9—H9B | 109.5 |
S3—Bi1—S1 | 86.949 (15) | H9A—C9—H9B | 109.5 |
S2—Bi1—S1 | 86.582 (15) | C11—C9—H9C | 109.5 |
Cl1i—Bi1—S1 | 108.598 (16) | H9A—C9—H9C | 109.5 |
Cl2—Bi1—Cl1 | 86.939 (18) | H9B—C9—H9C | 109.5 |
S3—Bi1—Cl1 | 102.541 (15) | C11—C10—H10A | 109.5 |
S2—Bi1—Cl1 | 166.327 (14) | C11—C10—H10B | 109.5 |
Cl1i—Bi1—Cl1 | 88.262 (15) | H10A—C10—H10B | 109.5 |
S1—Bi1—Cl1 | 92.814 (16) | C11—C10—H10C | 109.5 |
Bi1i—Cl1—Bi1 | 91.738 (15) | H10A—C10—H10C | 109.5 |
C5—S1—Bi1 | 103.01 (6) | H10B—C10—H10C | 109.5 |
C12—S2—Bi1 | 105.95 (6) | N3—C11—C8 | 108.35 (15) |
C19—S3—Bi1 | 106.11 (6) | N3—C11—C9 | 110.42 (14) |
C5—N1—C6 | 108.04 (15) | C8—C11—C9 | 112.19 (16) |
C5—N1—C4 | 127.44 (15) | N3—C11—C10 | 108.72 (15) |
C6—N1—C4 | 124.51 (14) | C8—C11—C10 | 109.60 (16) |
C5—N2—C7 | 108.25 (14) | C9—C11—C10 | 107.50 (15) |
C5—N2—B1 | 133.29 (15) | N4—C12—N3 | 108.17 (15) |
C7—N2—B1 | 118.34 (15) | N4—C12—S2 | 126.23 (13) |
C12—N3—C13 | 107.79 (14) | N3—C12—S2 | 125.59 (13) |
C12—N3—C11 | 128.24 (14) | C14—C13—N3 | 107.74 (16) |
C13—N3—C11 | 123.97 (14) | C14—C13—H13 | 126.1 |
C12—N4—C14 | 107.80 (15) | N3—C13—H13 | 126.1 |
C12—N4—B1 | 133.49 (15) | C13—C14—N4 | 108.45 (16) |
C14—N4—B1 | 118.60 (15) | C13—C14—H14 | 125.8 |
C19—N5—C20 | 108.11 (15) | N4—C14—H14 | 125.8 |
C19—N5—C18 | 127.96 (15) | C18—C15—H15A | 109.5 |
C20—N5—C18 | 123.93 (15) | C18—C15—H15B | 109.5 |
C19—N6—C21 | 107.90 (15) | H15A—C15—H15B | 109.5 |
C19—N6—B1 | 133.39 (15) | C18—C15—H15C | 109.5 |
C21—N6—B1 | 118.46 (15) | H15A—C15—H15C | 109.5 |
C4—C1—H1A | 109.5 | H15B—C15—H15C | 109.5 |
C4—C1—H1B | 109.5 | C18—C16—H16A | 109.5 |
H1A—C1—H1B | 109.5 | C18—C16—H16B | 109.5 |
C4—C1—H1C | 109.5 | H16A—C16—H16B | 109.5 |
H1A—C1—H1C | 109.5 | C18—C16—H16C | 109.5 |
H1B—C1—H1C | 109.5 | H16A—C16—H16C | 109.5 |
C4—C2—H2A | 109.5 | H16B—C16—H16C | 109.5 |
C4—C2—H2B | 109.5 | C18—C17—H17A | 109.5 |
H2A—C2—H2B | 109.5 | C18—C17—H17B | 109.5 |
C4—C2—H2C | 109.5 | H17A—C17—H17B | 109.5 |
H2A—C2—H2C | 109.5 | C18—C17—H17C | 109.5 |
H2B—C2—H2C | 109.5 | H17A—C17—H17C | 109.5 |
C4—C3—H3A | 109.5 | H17B—C17—H17C | 109.5 |
C4—C3—H3B | 109.5 | N5—C18—C15 | 109.08 (15) |
H3A—C3—H3B | 109.5 | N5—C18—C16 | 108.88 (16) |
C4—C3—H3C | 109.5 | C15—C18—C16 | 112.63 (18) |
H3A—C3—H3C | 109.5 | N5—C18—C17 | 108.47 (16) |
H3B—C3—H3C | 109.5 | C15—C18—C17 | 109.27 (18) |
N1—C4—C1 | 109.13 (15) | C16—C18—C17 | 108.43 (17) |
N1—C4—C3 | 108.54 (16) | N6—C19—N5 | 107.98 (15) |
C1—C4—C3 | 109.24 (17) | N6—C19—S3 | 125.53 (13) |
N1—C4—C2 | 109.24 (15) | N5—C19—S3 | 126.47 (14) |
C1—C4—C2 | 112.29 (18) | C21—C20—N5 | 107.37 (16) |
C3—C4—C2 | 108.33 (16) | C21—C20—H20 | 126.3 |
N2—C5—N1 | 107.40 (15) | N5—C20—H20 | 126.3 |
N2—C5—S1 | 126.30 (13) | C20—C21—N6 | 108.63 (16) |
N1—C5—S1 | 126.29 (14) | C20—C21—H21 | 125.7 |
C7—C6—N1 | 107.97 (16) | N6—C21—H21 | 125.7 |
C7—C6—H6 | 126.0 | N6—B1—N2 | 111.95 (15) |
N1—C6—H6 | 126.0 | N6—B1—N4 | 114.25 (15) |
C6—C7—N2 | 108.34 (16) | N2—B1—N4 | 112.26 (14) |
C6—C7—H7 | 125.8 | N6—B1—H1 | 105.9 |
N2—C7—H7 | 125.8 | N2—B1—H1 | 105.9 |
C11—C8—H8A | 109.5 | N4—B1—H1 | 105.9 |
C5—N1—C4—C1 | −61.3 (2) | C11—N3—C13—C14 | 178.21 (16) |
C6—N1—C4—C1 | 117.48 (19) | N3—C13—C14—N4 | 0.5 (2) |
C5—N1—C4—C3 | 179.70 (17) | C12—N4—C14—C13 | 0.9 (2) |
C6—N1—C4—C3 | −1.5 (2) | B1—N4—C14—C13 | −175.76 (16) |
C5—N1—C4—C2 | 61.8 (2) | C19—N5—C18—C15 | −63.0 (2) |
C6—N1—C4—C2 | −119.41 (19) | C20—N5—C18—C15 | 117.0 (2) |
C7—N2—C5—N1 | −0.31 (19) | C19—N5—C18—C16 | 60.3 (2) |
B1—N2—C5—N1 | −176.07 (17) | C20—N5—C18—C16 | −119.7 (2) |
C7—N2—C5—S1 | −178.81 (13) | C19—N5—C18—C17 | 178.08 (18) |
B1—N2—C5—S1 | 5.4 (3) | C20—N5—C18—C17 | −1.9 (3) |
C6—N1—C5—N2 | 0.53 (19) | C21—N6—C19—N5 | −0.84 (19) |
C4—N1—C5—N2 | 179.50 (15) | B1—N6—C19—N5 | −174.81 (17) |
C6—N1—C5—S1 | 179.03 (14) | C21—N6—C19—S3 | −179.12 (14) |
C4—N1—C5—S1 | −2.0 (3) | B1—N6—C19—S3 | 6.9 (3) |
Bi1—S1—C5—N2 | −72.74 (15) | C20—N5—C19—N6 | 1.25 (19) |
Bi1—S1—C5—N1 | 109.03 (15) | C18—N5—C19—N6 | −178.75 (16) |
C5—N1—C6—C7 | −0.6 (2) | C20—N5—C19—S3 | 179.52 (14) |
C4—N1—C6—C7 | −179.56 (16) | C18—N5—C19—S3 | −0.5 (3) |
N1—C6—C7—N2 | 0.4 (2) | Bi1—S3—C19—N6 | −75.54 (16) |
C5—N2—C7—C6 | 0.0 (2) | Bi1—S3—C19—N5 | 106.49 (15) |
B1—N2—C7—C6 | 176.46 (16) | C19—N5—C20—C21 | −1.2 (2) |
C12—N3—C11—C8 | −70.0 (2) | C18—N5—C20—C21 | 178.81 (17) |
C13—N3—C11—C8 | 110.14 (19) | N5—C20—C21—N6 | 0.7 (2) |
C12—N3—C11—C9 | 53.2 (2) | C19—N6—C21—C20 | 0.1 (2) |
C13—N3—C11—C9 | −126.62 (18) | B1—N6—C21—C20 | 175.12 (16) |
C12—N3—C11—C10 | 170.92 (16) | C19—N6—B1—N2 | 99.4 (2) |
C13—N3—C11—C10 | −8.9 (2) | C21—N6—B1—N2 | −74.0 (2) |
C14—N4—C12—N3 | −1.89 (19) | C19—N6—B1—N4 | −29.6 (3) |
B1—N4—C12—N3 | 174.02 (17) | C21—N6—B1—N4 | 156.96 (16) |
C14—N4—C12—S2 | 177.92 (14) | C5—N2—B1—N6 | −29.7 (3) |
B1—N4—C12—S2 | −6.2 (3) | C7—N2—B1—N6 | 154.84 (15) |
C13—N3—C12—N4 | 2.19 (19) | C5—N2—B1—N4 | 100.3 (2) |
C11—N3—C12—N4 | −177.66 (15) | C7—N2—B1—N4 | −75.1 (2) |
C13—N3—C12—S2 | −177.62 (13) | C12—N4—B1—N6 | 104.3 (2) |
C11—N3—C12—S2 | 2.5 (3) | C14—N4—B1—N6 | −80.2 (2) |
Bi1—S2—C12—N4 | −68.38 (16) | C12—N4—B1—N2 | −24.6 (3) |
Bi1—S2—C12—N3 | 111.39 (14) | C14—N4—B1—N2 | 150.95 (16) |
C12—N3—C13—C14 | −1.6 (2) |
Symmetry code: (i) −x+1, −y+1, −z+2. |
(I) | (II) | ||
Bi1—S1 | 2.6463 (6) | Bi1—S1 | 2.9128 (5) |
Bi1—S2 | 2.8307 (5) | Bi1—S2 | 2.7222 (5) |
Bi1—S3 | 2.7242 (4) | Bi1—S3 | 2.6931 (5) |
Bi1—Cl1 | 2.6933 (5) | Bi1—Cl1 | 2.9401 (6) |
Bi1—Cl2 | 2.7499 (4) | Bi1—Cl1i | 2.8915 (5) |
Bi1—O1 | 2.8023 (14) | Bi1—Cl2 | 2.5949 (5) |
Bi1···Bi1i | 4.1858 (5) | ||
S1—Bi1—Cl1 | 100.115 (14) | S1—Bi1—Cl1 | 92.814 (16) |
S2—Bi1—Cl1 | 160.302 (13) | S2—Bi1—Cl1 | 166.327 (14) |
S3—Bi1—Cl1 | 76.546 (13) | S3—Bi1—Cl1 | 102.541 (15) |
S1—Bi1—Cl2 | 74.926 (13) | S1—Bi1—Cl1i | 108.598 (16) |
S2—Bi1—Cl2 | 103.836 (14) | S2—Bi1—Cl1i | 79.020 (15) |
S3—Bi1—Cl2 | 160.381 (14) | S3—Bi1—Cl1i | 160.787 (15) |
S1—Bi1—S2 | 90.300 (14) | S1—Bi1—Cl2 | 164.283 (15) |
S1—Bi1—S3 | 88.960 (13) | S2—Bi1—Cl2 | 97.312 (17) |
S2—Bi1—S3 | 87.065 (14) | S3—Bi1—Cl2 | 77.787 (16) |
Cl1—Bi1—Cl2 | 95.046 (14) | S1—Bi1—S2 | 86.582 (15) |
S1—Bi1—O1 | 152.76 (4) | S1—Bi1—S3 | 86.949 (15) |
S2—Bi1—O1 | 74.07 (3) | S2—Bi1—S3 | 91.074 (15) |
S3—Bi1—O1 | 111.80 (4) | Cl1—Bi1—Cl2 | 86.939 (18) |
Cl1—Bi1—O1 | 101.73 (3) | Cl1—Bi1—Cl1i | 88.262 (15) |
Cl2—Bi1—O1 | 87.10 (4) | Cl1i—Bi1—Cl2 | 87.108 (17) |
Symmetry code: (i) -x+1, -y+1, -z+2. |
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