Crystal structure of bis­(1-mesityl-1H-imidazole-κN³)di­phenyl­boron tri­fluoro­methane­sulfonate

In this manuscript, we report the the crystal structure of di­phenyl­bis­(mesityl­imidazole)­borane tri­fluoro­methane­sulfonate. Weak inter­actions, such as π–π stacking are present in the structure.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](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

---

Computing details

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).

Bis(1-mesityl-1H-imidazole-κN³)diphenylboron trifluoromethanesulfonate,

Crystal data

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) Å^3	Plate, clear colourless
Z = 8	0.20 × 0.10 × 0.05 mm
F(000) = 2880

Data collection

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

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.084	H-atom parameters constrained
wR(F^2) = 0.225	w = 1/[σ^2(Fo^2) + (0.086P)^2] where P = (Fo^2 + 2Fc^2)/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

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

Bond angles around the boron center in Ph₂B(MesIm)₂OTf.

	N1 B1 N3	N1 B1 C1	N3 B1 C1	C1 B1 C7
Angle Measurements (°)	105.79	107.37	109.29	116.76