Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989020005058/jj2222sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2056989020005058/jj2222Isup3.hkl | |
Chemdraw file https://doi.org/10.1107/S2056989020005058/jj2222Isup4.cdx |
CCDC reference: 1983246
Key indicators
Structure: I- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.005 Å
- R factor = 0.084
- wR factor = 0.225
- Data-to-parameter ratio = 18.0
checkCIF/PLATON results
No syntax errors found
Alert level B RINTA01_ALERT_3_B The value of Rint is greater than 0.18 Rint given 0.207 PLAT020_ALERT_3_B The Value of Rint is Greater Than 0.12 ......... 0.207 Report
Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00528 Ang. PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 19.513 Check PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 3.811 Check PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 3 Report PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density. 0 Info
Alert level G PLAT244_ALERT_4_G Low Solvent Ueq as Compared to Neighbors of C37 Check PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 2 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 16 Note PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF .... 1 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 2 ALERT level B = A potentially serious problem, consider carefully 5 ALERT level C = Check. Ensure it is not caused by an omission or oversight 4 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 8 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
C36H38BN4+·CF3O3S− | Dx = 1.297 Mg m−3 |
Mr = 686.58 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbcn | Cell parameters from 783 reflections |
a = 28.661 (4) Å | θ = 2.7–22.0° |
b = 15.979 (3) Å | µ = 0.15 mm−1 |
c = 15.352 (3) Å | T = 100 K |
V = 7031 (2) Å3 | Plate, clear colourless |
Z = 8 | 0.20 × 0.10 × 0.05 mm |
F(000) = 2880 |
Bruker Venture D8 diffractometer | 4090 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.207 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | θmax = 27.5°, θmin = 2.0° |
Tmin = 0.620, Tmax = 0.746 | h = −37→37 |
55395 measured reflections | k = −20→17 |
8077 independent reflections | l = −16→19 |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.084 | H-atom parameters constrained |
wR(F2) = 0.225 | w = 1/[σ2(Fo2) + (0.086P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
8077 reflections | Δρmax = 0.29 e Å−3 |
448 parameters | Δρmin = −0.56 e Å−3 |
0 restraints |
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. A colorless crystal (plate, approximate dimensions 0.20 × 0.10 × 0.05 mm3) was placed onto the tip of a MiTeGen pin and mounted on a Bruker Venture D8 diffractometer equipped with a Photon II detector at 100.0 K. The data collection was carried out using Mo Kα radiation (λ = 0.71073 Å, graphite monochromator) with a frame time of 0.5 seconds and a detector distance of 50 mm. Complete data to a resolution of 0.77 Å with a redundancy of 4 were collected. The frames were integrated with the Bruker software package SAINT using a narrow-frame algorithm (Bruker, 2016) to a resolution of 0.77 Å. The space group Pbcn was determined based on intensity statistics and systematic absences. The structure was solved using SHELXT (Sheldrick, 2015) and refined using full-matrix least-squares on F2with the OLEX2 suite (Dolomanov et al., 2009). An intrinsic phasing solution was calculated, which provided most non-hydrogen atoms from the E-map. Full-matrix least squares / difference Fourier cycles were performed, which located the remaining non-hydrogen atoms. All non-hydrogen atoms were refined with anisotropic displacement parameters. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.33052 (3) | 0.51497 (7) | 0.84291 (6) | 0.0314 (3) | |
F3 | 0.28584 (8) | 0.47946 (19) | 0.98737 (17) | 0.0591 (8) | |
O2 | 0.36630 (8) | 0.55684 (18) | 0.89278 (18) | 0.0381 (7) | |
O3 | 0.33701 (8) | 0.42598 (18) | 0.83416 (18) | 0.0382 (7) | |
N4 | 0.41363 (9) | 0.56867 (19) | 0.61232 (19) | 0.0243 (7) | |
F2 | 0.24174 (8) | 0.4902 (2) | 0.87503 (19) | 0.0667 (9) | |
N3 | 0.38087 (9) | 0.69119 (19) | 0.63308 (19) | 0.0243 (7) | |
F1 | 0.27011 (9) | 0.6001 (2) | 0.9347 (2) | 0.0737 (9) | |
N1 | 0.31506 (9) | 0.7835 (2) | 0.6882 (2) | 0.0294 (7) | |
N2 | 0.24087 (9) | 0.7535 (2) | 0.6981 (2) | 0.0295 (7) | |
O1 | 0.31616 (10) | 0.5576 (2) | 0.76506 (19) | 0.0504 (8) | |
C27 | 0.40732 (11) | 0.6326 (2) | 0.6686 (2) | 0.0240 (8) | |
H27 | 0.420079 | 0.635150 | 0.725618 | 0.029* | |
C26 | 0.38945 (11) | 0.5878 (2) | 0.5366 (2) | 0.0261 (8) | |
H26 | 0.387282 | 0.554329 | 0.485583 | 0.031* | |
C6 | 0.38221 (12) | 0.7486 (2) | 0.8345 (2) | 0.0281 (8) | |
H6 | 0.356319 | 0.711763 | 0.829601 | 0.034* | |
C28 | 0.44454 (11) | 0.4982 (2) | 0.6233 (2) | 0.0239 (8) | |
C25 | 0.36961 (11) | 0.6633 (2) | 0.5499 (2) | 0.0275 (8) | |
H25 | 0.350952 | 0.692778 | 0.508910 | 0.033* | |
C30 | 0.45687 (12) | 0.3513 (2) | 0.6343 (2) | 0.0292 (8) | |
H30 | 0.444921 | 0.295880 | 0.636712 | 0.035* | |
C15 | 0.28330 (11) | 0.7240 (3) | 0.6763 (2) | 0.0288 (9) | |
H15 | 0.289568 | 0.669035 | 0.655722 | 0.035* | |
C33 | 0.49270 (11) | 0.5138 (2) | 0.6266 (2) | 0.0257 (8) | |
C29 | 0.42563 (12) | 0.4176 (2) | 0.6266 (2) | 0.0270 (8) | |
C1 | 0.39593 (11) | 0.7953 (2) | 0.7613 (2) | 0.0273 (8) | |
C16 | 0.19747 (11) | 0.7084 (2) | 0.6921 (2) | 0.0293 (9) | |
C2 | 0.43327 (11) | 0.8508 (2) | 0.7742 (2) | 0.0284 (8) | |
H2 | 0.443153 | 0.884817 | 0.726861 | 0.034* | |
C32 | 0.52197 (11) | 0.4447 (3) | 0.6345 (2) | 0.0291 (9) | |
H32 | 0.554723 | 0.453509 | 0.637309 | 0.035* | |
C21 | 0.17238 (12) | 0.6943 (2) | 0.7690 (2) | 0.0310 (9) | |
C36 | 0.51244 (12) | 0.6001 (2) | 0.6162 (3) | 0.0307 (9) | |
H36A | 0.499383 | 0.626166 | 0.563814 | 0.046* | |
H36B | 0.546454 | 0.596740 | 0.610783 | 0.046* | |
H36C | 0.504378 | 0.633941 | 0.667323 | 0.046* | |
C5 | 0.40513 (12) | 0.7545 (3) | 0.9134 (3) | 0.0326 (9) | |
H5 | 0.395486 | 0.720892 | 0.961213 | 0.039* | |
C7 | 0.38224 (12) | 0.8477 (2) | 0.5930 (2) | 0.0295 (9) | |
C31 | 0.50495 (12) | 0.3631 (3) | 0.6386 (2) | 0.0306 (9) | |
C17 | 0.18141 (12) | 0.6840 (3) | 0.6106 (2) | 0.0299 (9) | |
C12 | 0.42784 (12) | 0.8482 (3) | 0.5586 (2) | 0.0321 (9) | |
H12 | 0.450052 | 0.809883 | 0.581303 | 0.038* | |
C19 | 0.11264 (12) | 0.6264 (3) | 0.6814 (3) | 0.0331 (9) | |
C20 | 0.12978 (13) | 0.6533 (3) | 0.7608 (3) | 0.0344 (9) | |
H20 | 0.111768 | 0.643484 | 0.811775 | 0.041* | |
C34 | 0.37388 (11) | 0.4017 (3) | 0.6219 (3) | 0.0329 (9) | |
H34A | 0.357322 | 0.444354 | 0.655747 | 0.049* | |
H34B | 0.366979 | 0.346176 | 0.645772 | 0.049* | |
H34C | 0.363669 | 0.404164 | 0.561004 | 0.049* | |
C13 | 0.29209 (12) | 0.8530 (3) | 0.7202 (3) | 0.0340 (9) | |
H13 | 0.306240 | 0.904756 | 0.735551 | 0.041* | |
C14 | 0.24595 (12) | 0.8351 (3) | 0.7261 (3) | 0.0361 (10) | |
H14 | 0.221897 | 0.871463 | 0.745661 | 0.043* | |
C3 | 0.45621 (12) | 0.8580 (3) | 0.8530 (3) | 0.0338 (9) | |
H3 | 0.481451 | 0.896091 | 0.859329 | 0.041* | |
C8 | 0.35079 (13) | 0.9032 (3) | 0.5542 (3) | 0.0349 (9) | |
H8 | 0.319328 | 0.903991 | 0.573675 | 0.042* | |
C11 | 0.44155 (14) | 0.9023 (3) | 0.4933 (2) | 0.0374 (10) | |
H11 | 0.472803 | 0.901466 | 0.472694 | 0.045* | |
C10 | 0.40973 (14) | 0.9575 (3) | 0.4579 (3) | 0.0406 (10) | |
H10 | 0.419101 | 0.995255 | 0.413444 | 0.049* | |
C22 | 0.20862 (12) | 0.7009 (3) | 0.5280 (2) | 0.0386 (10) | |
H22A | 0.219943 | 0.758818 | 0.528540 | 0.058* | |
H22B | 0.188329 | 0.692459 | 0.477424 | 0.058* | |
H22C | 0.235230 | 0.662562 | 0.524665 | 0.058* | |
C18 | 0.13875 (12) | 0.6426 (3) | 0.6070 (3) | 0.0329 (9) | |
H18 | 0.127120 | 0.624903 | 0.552073 | 0.039* | |
C4 | 0.44202 (12) | 0.8092 (3) | 0.9228 (3) | 0.0356 (10) | |
H4 | 0.457721 | 0.813342 | 0.977122 | 0.043* | |
C37 | 0.28007 (13) | 0.5219 (3) | 0.9132 (3) | 0.0418 (11) | |
C9 | 0.36438 (15) | 0.9577 (3) | 0.4874 (3) | 0.0425 (11) | |
H9 | 0.342258 | 0.994901 | 0.462425 | 0.051* | |
C23 | 0.06599 (13) | 0.5824 (3) | 0.6753 (3) | 0.0444 (11) | |
H23A | 0.056297 | 0.564060 | 0.733422 | 0.067* | |
H23B | 0.068812 | 0.533700 | 0.636871 | 0.067* | |
H23C | 0.042650 | 0.621045 | 0.651571 | 0.067* | |
C35 | 0.53809 (14) | 0.2904 (3) | 0.6448 (3) | 0.0426 (11) | |
H35A | 0.524844 | 0.247568 | 0.683221 | 0.064* | |
H35B | 0.567944 | 0.309684 | 0.668652 | 0.064* | |
H35C | 0.543085 | 0.266699 | 0.586731 | 0.064* | |
C24 | 0.18976 (15) | 0.7225 (3) | 0.8564 (3) | 0.0419 (11) | |
H24A | 0.223609 | 0.714367 | 0.859655 | 0.063* | |
H24B | 0.174540 | 0.689721 | 0.902275 | 0.063* | |
H24C | 0.182489 | 0.781963 | 0.864474 | 0.063* | |
B1 | 0.36969 (13) | 0.7823 (3) | 0.6694 (3) | 0.0273 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0263 (5) | 0.0332 (6) | 0.0347 (6) | −0.0018 (4) | −0.0037 (4) | 0.0032 (5) |
F3 | 0.0434 (14) | 0.083 (2) | 0.0510 (17) | −0.0021 (13) | 0.0132 (12) | 0.0086 (15) |
O2 | 0.0316 (13) | 0.0371 (18) | 0.0456 (17) | −0.0116 (12) | −0.0116 (12) | 0.0105 (14) |
O3 | 0.0362 (14) | 0.0332 (18) | 0.0453 (18) | 0.0009 (12) | −0.0041 (12) | −0.0057 (14) |
N4 | 0.0203 (13) | 0.0241 (18) | 0.0284 (17) | −0.0011 (12) | 0.0002 (12) | −0.0022 (14) |
F2 | 0.0227 (12) | 0.104 (3) | 0.074 (2) | −0.0032 (13) | −0.0044 (12) | −0.0208 (17) |
N3 | 0.0224 (13) | 0.0230 (18) | 0.0274 (16) | 0.0024 (12) | −0.0004 (12) | −0.0012 (13) |
F1 | 0.0653 (17) | 0.062 (2) | 0.093 (2) | 0.0289 (15) | −0.0020 (16) | −0.0247 (18) |
N1 | 0.0237 (15) | 0.032 (2) | 0.0327 (18) | 0.0071 (13) | 0.0000 (13) | −0.0064 (15) |
N2 | 0.0241 (14) | 0.035 (2) | 0.0296 (17) | 0.0062 (13) | −0.0014 (12) | −0.0038 (15) |
O1 | 0.0512 (17) | 0.056 (2) | 0.0436 (18) | 0.0009 (15) | −0.0141 (14) | 0.0211 (16) |
C27 | 0.0231 (16) | 0.025 (2) | 0.0240 (19) | 0.0029 (14) | −0.0004 (14) | −0.0023 (16) |
C26 | 0.0218 (16) | 0.031 (2) | 0.0260 (19) | 0.0007 (14) | −0.0050 (14) | −0.0003 (17) |
C6 | 0.0257 (17) | 0.026 (2) | 0.032 (2) | 0.0032 (15) | −0.0004 (15) | 0.0009 (17) |
C28 | 0.0225 (16) | 0.023 (2) | 0.0264 (19) | 0.0016 (14) | 0.0017 (14) | 0.0023 (16) |
C25 | 0.0245 (17) | 0.031 (2) | 0.027 (2) | 0.0037 (15) | −0.0036 (14) | −0.0006 (17) |
C30 | 0.0357 (19) | 0.022 (2) | 0.030 (2) | 0.0009 (16) | 0.0035 (16) | −0.0021 (17) |
C15 | 0.0232 (17) | 0.029 (2) | 0.034 (2) | 0.0039 (15) | 0.0004 (15) | −0.0005 (17) |
C33 | 0.0276 (17) | 0.026 (2) | 0.0239 (19) | 0.0010 (15) | 0.0032 (15) | 0.0006 (16) |
C29 | 0.0301 (17) | 0.029 (2) | 0.0215 (18) | 0.0014 (15) | 0.0007 (15) | −0.0025 (16) |
C1 | 0.0220 (16) | 0.031 (2) | 0.029 (2) | 0.0064 (15) | 0.0007 (14) | −0.0009 (17) |
C16 | 0.0220 (17) | 0.031 (2) | 0.035 (2) | 0.0079 (15) | −0.0015 (15) | −0.0008 (18) |
C2 | 0.0299 (18) | 0.028 (2) | 0.027 (2) | −0.0007 (15) | 0.0064 (15) | −0.0011 (17) |
C32 | 0.0225 (17) | 0.039 (3) | 0.026 (2) | 0.0063 (16) | 0.0024 (14) | 0.0012 (17) |
C21 | 0.0345 (19) | 0.030 (2) | 0.028 (2) | 0.0065 (16) | 0.0003 (16) | 0.0022 (18) |
C36 | 0.0255 (17) | 0.031 (2) | 0.036 (2) | −0.0025 (16) | 0.0002 (16) | −0.0020 (18) |
C5 | 0.0328 (19) | 0.034 (3) | 0.030 (2) | 0.0057 (17) | 0.0022 (16) | −0.0023 (18) |
C7 | 0.0296 (18) | 0.030 (2) | 0.029 (2) | 0.0014 (16) | −0.0075 (15) | −0.0033 (17) |
C31 | 0.0338 (19) | 0.034 (3) | 0.0237 (19) | 0.0104 (17) | 0.0036 (15) | −0.0027 (17) |
C17 | 0.0259 (17) | 0.034 (2) | 0.030 (2) | 0.0058 (16) | 0.0019 (15) | 0.0011 (18) |
C12 | 0.0360 (19) | 0.030 (2) | 0.031 (2) | −0.0008 (16) | −0.0001 (16) | −0.0005 (18) |
C19 | 0.0269 (18) | 0.030 (2) | 0.042 (2) | 0.0043 (16) | 0.0011 (16) | 0.0012 (19) |
C20 | 0.036 (2) | 0.031 (2) | 0.037 (2) | 0.0047 (17) | 0.0059 (17) | 0.0034 (19) |
C34 | 0.0302 (19) | 0.031 (2) | 0.038 (2) | −0.0092 (16) | 0.0029 (16) | 0.0004 (19) |
C13 | 0.0305 (19) | 0.028 (2) | 0.044 (2) | 0.0026 (16) | 0.0009 (17) | −0.0080 (19) |
C14 | 0.0243 (18) | 0.041 (3) | 0.043 (2) | 0.0059 (16) | −0.0004 (16) | −0.010 (2) |
C3 | 0.0292 (18) | 0.035 (3) | 0.038 (2) | −0.0032 (16) | 0.0025 (16) | −0.0080 (19) |
C8 | 0.041 (2) | 0.030 (3) | 0.033 (2) | 0.0017 (17) | −0.0090 (17) | −0.0038 (19) |
C11 | 0.047 (2) | 0.040 (3) | 0.025 (2) | −0.0025 (19) | 0.0048 (17) | 0.0006 (19) |
C10 | 0.059 (3) | 0.029 (3) | 0.034 (2) | −0.011 (2) | −0.005 (2) | 0.002 (2) |
C22 | 0.0320 (19) | 0.054 (3) | 0.030 (2) | −0.0007 (18) | 0.0011 (16) | −0.005 (2) |
C18 | 0.0287 (18) | 0.036 (3) | 0.034 (2) | 0.0064 (16) | −0.0025 (16) | −0.0002 (19) |
C4 | 0.0278 (19) | 0.048 (3) | 0.031 (2) | 0.0030 (17) | −0.0006 (16) | −0.006 (2) |
C37 | 0.030 (2) | 0.048 (3) | 0.047 (3) | 0.0011 (19) | −0.0069 (18) | −0.005 (2) |
C9 | 0.053 (3) | 0.032 (3) | 0.042 (3) | 0.0027 (19) | −0.016 (2) | 0.006 (2) |
C23 | 0.036 (2) | 0.038 (3) | 0.059 (3) | −0.0036 (18) | 0.003 (2) | 0.001 (2) |
C35 | 0.042 (2) | 0.041 (3) | 0.045 (3) | 0.0127 (19) | 0.0011 (19) | −0.006 (2) |
C24 | 0.058 (3) | 0.041 (3) | 0.027 (2) | 0.000 (2) | 0.0003 (19) | 0.0040 (19) |
B1 | 0.0191 (18) | 0.024 (3) | 0.038 (3) | 0.0029 (16) | −0.0023 (17) | 0.000 (2) |
S1—O2 | 1.444 (3) | C36—H36B | 0.9800 |
S1—O3 | 1.440 (3) | C36—H36C | 0.9800 |
S1—O1 | 1.436 (3) | C5—H5 | 0.9500 |
S1—C37 | 1.808 (4) | C5—C4 | 1.379 (5) |
F3—C37 | 1.335 (5) | C7—C12 | 1.410 (5) |
N4—C27 | 1.350 (4) | C7—C8 | 1.398 (5) |
N4—C26 | 1.387 (4) | C7—B1 | 1.611 (6) |
N4—C28 | 1.443 (4) | C31—C35 | 1.503 (5) |
F2—C37 | 1.344 (4) | C17—C22 | 1.513 (5) |
N3—C27 | 1.322 (4) | C17—C18 | 1.391 (5) |
N3—C25 | 1.391 (4) | C12—H12 | 0.9500 |
N3—B1 | 1.592 (5) | C12—C11 | 1.381 (5) |
F1—C37 | 1.323 (5) | C19—C20 | 1.384 (5) |
N1—C15 | 1.330 (5) | C19—C18 | 1.389 (5) |
N1—C13 | 1.382 (5) | C19—C23 | 1.513 (5) |
N1—B1 | 1.592 (5) | C20—H20 | 0.9500 |
N2—C15 | 1.347 (4) | C34—H34A | 0.9800 |
N2—C16 | 1.441 (5) | C34—H34B | 0.9800 |
N2—C14 | 1.380 (5) | C34—H34C | 0.9800 |
C27—H27 | 0.9500 | C13—H13 | 0.9500 |
C26—H26 | 0.9500 | C13—C14 | 1.356 (5) |
C26—C25 | 1.350 (5) | C14—H14 | 0.9500 |
C6—H6 | 0.9500 | C3—H3 | 0.9500 |
C6—C1 | 1.406 (5) | C3—C4 | 1.387 (5) |
C6—C5 | 1.381 (5) | C8—H8 | 0.9500 |
C28—C33 | 1.404 (5) | C8—C9 | 1.401 (6) |
C28—C29 | 1.398 (5) | C11—H11 | 0.9500 |
C25—H25 | 0.9500 | C11—C10 | 1.380 (6) |
C30—H30 | 0.9500 | C10—H10 | 0.9500 |
C30—C29 | 1.392 (5) | C10—C9 | 1.376 (6) |
C30—C31 | 1.392 (5) | C22—H22A | 0.9800 |
C15—H15 | 0.9500 | C22—H22B | 0.9800 |
C33—C32 | 1.392 (5) | C22—H22C | 0.9800 |
C33—C36 | 1.500 (5) | C18—H18 | 0.9500 |
C29—C34 | 1.507 (5) | C4—H4 | 0.9500 |
C1—C2 | 1.405 (5) | C9—H9 | 0.9500 |
C1—B1 | 1.611 (5) | C23—H23A | 0.9800 |
C16—C21 | 1.400 (5) | C23—H23B | 0.9800 |
C16—C17 | 1.390 (5) | C23—H23C | 0.9800 |
C2—H2 | 0.9500 | C35—H35A | 0.9800 |
C2—C3 | 1.382 (5) | C35—H35B | 0.9800 |
C32—H32 | 0.9500 | C35—H35C | 0.9800 |
C32—C31 | 1.394 (5) | C24—H24A | 0.9800 |
C21—C20 | 1.391 (5) | C24—H24B | 0.9800 |
C21—C24 | 1.502 (5) | C24—H24C | 0.9800 |
C36—H36A | 0.9800 | ||
O2—S1—C37 | 102.90 (18) | C7—C12—H12 | 118.6 |
O3—S1—O2 | 114.52 (16) | C11—C12—C7 | 122.7 (4) |
O3—S1—C37 | 102.7 (2) | C11—C12—H12 | 118.6 |
O1—S1—O2 | 115.16 (18) | C20—C19—C18 | 118.4 (3) |
O1—S1—O3 | 115.30 (19) | C20—C19—C23 | 120.8 (4) |
O1—S1—C37 | 103.82 (19) | C18—C19—C23 | 120.8 (4) |
C27—N4—C26 | 107.6 (3) | C21—C20—H20 | 118.8 |
C27—N4—C28 | 126.7 (3) | C19—C20—C21 | 122.5 (4) |
C26—N4—C28 | 125.2 (3) | C19—C20—H20 | 118.8 |
C27—N3—C25 | 106.6 (3) | C29—C34—H34A | 109.5 |
C27—N3—B1 | 128.2 (3) | C29—C34—H34B | 109.5 |
C25—N3—B1 | 124.6 (3) | C29—C34—H34C | 109.5 |
C15—N1—C13 | 107.4 (3) | H34A—C34—H34B | 109.5 |
C15—N1—B1 | 129.8 (3) | H34A—C34—H34C | 109.5 |
C13—N1—B1 | 122.9 (3) | H34B—C34—H34C | 109.5 |
C15—N2—C16 | 126.0 (3) | N1—C13—H13 | 125.7 |
C15—N2—C14 | 108.3 (3) | C14—C13—N1 | 108.6 (4) |
C14—N2—C16 | 125.7 (3) | C14—C13—H13 | 125.7 |
N4—C27—H27 | 124.8 | N2—C14—H14 | 126.8 |
N3—C27—N4 | 110.4 (3) | C13—C14—N2 | 106.4 (3) |
N3—C27—H27 | 124.8 | C13—C14—H14 | 126.8 |
N4—C26—H26 | 126.9 | C2—C3—H3 | 120.3 |
C25—C26—N4 | 106.3 (3) | C2—C3—C4 | 119.4 (4) |
C25—C26—H26 | 126.9 | C4—C3—H3 | 120.3 |
C1—C6—H6 | 118.9 | C7—C8—H8 | 119.1 |
C5—C6—H6 | 118.9 | C7—C8—C9 | 121.8 (4) |
C5—C6—C1 | 122.2 (3) | C9—C8—H8 | 119.1 |
C33—C28—N4 | 118.0 (3) | C12—C11—H11 | 120.1 |
C29—C28—N4 | 119.0 (3) | C10—C11—C12 | 119.8 (4) |
C29—C28—C33 | 122.9 (3) | C10—C11—H11 | 120.1 |
N3—C25—H25 | 125.5 | C11—C10—H10 | 120.1 |
C26—C25—N3 | 109.1 (3) | C9—C10—C11 | 119.8 (4) |
C26—C25—H25 | 125.5 | C9—C10—H10 | 120.1 |
C29—C30—H30 | 118.7 | C17—C22—H22A | 109.5 |
C31—C30—H30 | 118.7 | C17—C22—H22B | 109.5 |
C31—C30—C29 | 122.5 (4) | C17—C22—H22C | 109.5 |
N1—C15—N2 | 109.4 (3) | H22A—C22—H22B | 109.5 |
N1—C15—H15 | 125.3 | H22A—C22—H22C | 109.5 |
N2—C15—H15 | 125.3 | H22B—C22—H22C | 109.5 |
C28—C33—C36 | 122.0 (3) | C17—C18—H18 | 119.0 |
C32—C33—C28 | 117.1 (3) | C19—C18—C17 | 122.0 (4) |
C32—C33—C36 | 120.8 (3) | C19—C18—H18 | 119.0 |
C28—C29—C34 | 122.4 (3) | C5—C4—C3 | 120.1 (4) |
C30—C29—C28 | 117.1 (3) | C5—C4—H4 | 120.0 |
C30—C29—C34 | 120.6 (4) | C3—C4—H4 | 120.0 |
C6—C1—B1 | 120.1 (3) | F3—C37—S1 | 112.3 (3) |
C2—C1—C6 | 115.8 (3) | F3—C37—F2 | 106.4 (4) |
C2—C1—B1 | 124.1 (3) | F2—C37—S1 | 111.7 (3) |
C21—C16—N2 | 118.1 (3) | F1—C37—S1 | 112.3 (3) |
C17—C16—N2 | 119.0 (3) | F1—C37—F3 | 107.1 (4) |
C17—C16—C21 | 122.9 (3) | F1—C37—F2 | 106.7 (3) |
C1—C2—H2 | 118.7 | C8—C9—H9 | 119.9 |
C3—C2—C1 | 122.6 (4) | C10—C9—C8 | 120.1 (4) |
C3—C2—H2 | 118.7 | C10—C9—H9 | 119.9 |
C33—C32—H32 | 118.8 | C19—C23—H23A | 109.5 |
C33—C32—C31 | 122.3 (3) | C19—C23—H23B | 109.5 |
C31—C32—H32 | 118.8 | C19—C23—H23C | 109.5 |
C16—C21—C24 | 122.3 (3) | H23A—C23—H23B | 109.5 |
C20—C21—C16 | 116.8 (3) | H23A—C23—H23C | 109.5 |
C20—C21—C24 | 120.9 (3) | H23B—C23—H23C | 109.5 |
C33—C36—H36A | 109.5 | C31—C35—H35A | 109.5 |
C33—C36—H36B | 109.5 | C31—C35—H35B | 109.5 |
C33—C36—H36C | 109.5 | C31—C35—H35C | 109.5 |
H36A—C36—H36B | 109.5 | H35A—C35—H35B | 109.5 |
H36A—C36—H36C | 109.5 | H35A—C35—H35C | 109.5 |
H36B—C36—H36C | 109.5 | H35B—C35—H35C | 109.5 |
C6—C5—H5 | 120.0 | C21—C24—H24A | 109.5 |
C4—C5—C6 | 120.0 (4) | C21—C24—H24B | 109.5 |
C4—C5—H5 | 120.0 | C21—C24—H24C | 109.5 |
C12—C7—B1 | 119.0 (3) | H24A—C24—H24B | 109.5 |
C8—C7—C12 | 115.7 (4) | H24A—C24—H24C | 109.5 |
C8—C7—B1 | 125.3 (3) | H24B—C24—H24C | 109.5 |
C30—C31—C32 | 118.1 (3) | N3—B1—C1 | 109.3 (3) |
C30—C31—C35 | 121.6 (4) | N3—B1—C7 | 107.0 (3) |
C32—C31—C35 | 120.3 (3) | N1—B1—N3 | 105.8 (3) |
C16—C17—C22 | 122.2 (3) | N1—B1—C1 | 107.4 (3) |
C16—C17—C18 | 117.4 (3) | N1—B1—C7 | 110.1 (3) |
C18—C17—C22 | 120.4 (3) | C7—B1—C1 | 116.7 (3) |
O2—S1—C37—F3 | −64.4 (3) | C29—C30—C31—C32 | −0.3 (5) |
O2—S1—C37—F2 | 176.1 (3) | C29—C30—C31—C35 | −178.6 (3) |
O2—S1—C37—F1 | 56.3 (3) | C1—C6—C5—C4 | 1.7 (6) |
O3—S1—C37—F3 | 54.8 (3) | C1—C2—C3—C4 | −0.3 (6) |
O3—S1—C37—F2 | −64.6 (4) | C16—N2—C15—N1 | 178.4 (3) |
O3—S1—C37—F1 | 175.5 (3) | C16—N2—C14—C13 | −179.0 (3) |
N4—C26—C25—N3 | −0.4 (4) | C16—C21—C20—C19 | 0.8 (6) |
N4—C28—C33—C32 | −178.1 (3) | C16—C17—C18—C19 | 0.5 (6) |
N4—C28—C33—C36 | −2.0 (5) | C2—C1—B1—N3 | 111.7 (4) |
N4—C28—C29—C30 | 177.9 (3) | C2—C1—B1—N1 | −134.0 (3) |
N4—C28—C29—C34 | −1.9 (5) | C2—C1—B1—C7 | −9.8 (5) |
N1—C13—C14—N2 | 0.5 (4) | C2—C3—C4—C5 | −0.5 (6) |
N2—C16—C21—C20 | 177.6 (3) | C21—C16—C17—C22 | 179.0 (4) |
N2—C16—C21—C24 | −1.5 (5) | C21—C16—C17—C18 | −1.0 (6) |
N2—C16—C17—C22 | 1.8 (5) | C36—C33—C32—C31 | −175.8 (3) |
N2—C16—C17—C18 | −178.2 (3) | C5—C6—C1—C2 | −2.4 (5) |
O1—S1—C37—F3 | 175.2 (3) | C5—C6—C1—B1 | 176.7 (3) |
O1—S1—C37—F2 | 55.8 (4) | C7—C12—C11—C10 | −1.3 (6) |
O1—S1—C37—F1 | −64.1 (3) | C7—C8—C9—C10 | 0.2 (6) |
C27—N4—C26—C25 | 0.5 (4) | C31—C30—C29—C28 | 0.0 (5) |
C27—N4—C28—C33 | −64.4 (5) | C31—C30—C29—C34 | 179.8 (3) |
C27—N4—C28—C29 | 118.2 (4) | C17—C16—C21—C20 | 0.4 (6) |
C27—N3—C25—C26 | 0.2 (4) | C17—C16—C21—C24 | −178.8 (4) |
C27—N3—B1—N1 | −115.8 (4) | C12—C7—C8—C9 | −2.0 (6) |
C27—N3—B1—C1 | −0.5 (5) | C12—C7—B1—N3 | −57.2 (4) |
C27—N3—B1—C7 | 126.8 (3) | C12—C7—B1—N1 | −171.7 (3) |
C26—N4—C27—N3 | −0.3 (4) | C12—C7—B1—C1 | 65.5 (5) |
C26—N4—C28—C33 | 107.0 (4) | C12—C11—C10—C9 | −0.7 (6) |
C26—N4—C28—C29 | −70.4 (4) | C20—C19—C18—C17 | 0.6 (6) |
C6—C1—C2—C3 | 1.7 (5) | C13—N1—C15—N2 | 1.1 (4) |
C6—C1—B1—N3 | −67.4 (4) | C13—N1—B1—N3 | −179.6 (3) |
C6—C1—B1—N1 | 47.0 (4) | C13—N1—B1—C1 | 63.8 (4) |
C6—C1—B1—C7 | 171.1 (3) | C13—N1—B1—C7 | −64.3 (4) |
C6—C5—C4—C3 | −0.2 (6) | C14—N2—C15—N1 | −0.8 (4) |
C28—N4—C27—N3 | 172.3 (3) | C14—N2—C16—C21 | −62.5 (5) |
C28—N4—C26—C25 | −172.3 (3) | C14—N2—C16—C17 | 114.8 (4) |
C28—C33—C32—C31 | 0.4 (5) | C8—C7—C12—C11 | 2.6 (6) |
C25—N3—C27—N4 | 0.1 (4) | C8—C7—B1—N3 | 120.2 (4) |
C25—N3—B1—N1 | 74.4 (4) | C8—C7—B1—N1 | 5.6 (5) |
C25—N3—B1—C1 | −170.2 (3) | C8—C7—B1—C1 | −117.1 (4) |
C25—N3—B1—C7 | −43.0 (4) | C11—C10—C9—C8 | 1.2 (6) |
C15—N1—C13—C14 | −1.0 (4) | C22—C17—C18—C19 | −179.6 (4) |
C15—N1—B1—N3 | −1.0 (5) | C18—C19—C20—C21 | −1.3 (6) |
C15—N1—B1—C1 | −117.6 (4) | C23—C19—C20—C21 | −179.7 (4) |
C15—N1—B1—C7 | 114.3 (4) | C23—C19—C18—C17 | 179.1 (4) |
C15—N2—C16—C21 | 118.4 (4) | C24—C21—C20—C19 | 180.0 (4) |
C15—N2—C16—C17 | −64.2 (5) | B1—N3—C27—N4 | −171.2 (3) |
C15—N2—C14—C13 | 0.2 (4) | B1—N3—C25—C26 | 171.9 (3) |
C33—C28—C29—C30 | 0.6 (5) | B1—N1—C15—N2 | −177.7 (3) |
C33—C28—C29—C34 | −179.2 (3) | B1—N1—C13—C14 | 177.9 (3) |
C33—C32—C31—C30 | 0.1 (5) | B1—C1—C2—C3 | −177.4 (3) |
C33—C32—C31—C35 | 178.4 (3) | B1—C7—C12—C11 | −179.8 (4) |
C29—C28—C33—C32 | −0.8 (5) | B1—C7—C8—C9 | −179.5 (4) |
C29—C28—C33—C36 | 175.3 (3) |
Distance | Angle | |
C26···S1i | 3.793 (4) | 149.4 |
C26···O2i | 3.264 (5) | 160.0 |
C15···O1 | 3.132 (5) | 118.7 |
C14···O3ii | 3.242 (5) | 159.4 |
N3—C27···O1 | 3.529 (3) | 125.0 |
Symmetry codes: (i) x, -y + 1, z - 1/2; (ii) -x + 1/2, y + 1/2, z. |
N1 B1 N3 | N1 B1 C1 | N3 B1 C1 | C1 B1 C7 | |
Angle Measurements (°) | 105.79 | 107.37 | 109.29 | 116.76 |