A novel sulfon­amide containing a boronate ester group

A novel sulfon­amide containing a boronate ester group, name­ly N-[3-(4,4,5,5-tetra­methyl-1,3,2-dioxaborolan-2-yl)­phenyl]-N-(2,4,6-tri­methyl­benzyl)-p-toluene­sulfon­amide,C₂₉H₃₆BNO₄S, crystallizes with two independent mol­ecules in the asymmetric unit. The Lewis-acid B atom is in a trigonal-planar environment and is not involved in inter- or secondary intramolecular interactions.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.053
• wR factor = 0.154
• Data-to-parameter ratio = 29.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: SMART (Bruker, 1997-1999); cell refinement: SMART; data reduction: SHELXTL (Sheldrick, 1997a); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997b); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-N-(2,4,6- trimethylbenzyl)-p-toluenesulfonamide

Crystal data

C29H36BNO4S	Z = 4
Mr = 505.46	F(000) = 1080
Triclinic, P1	Dx = 1.198 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 12.7798 (9) Å	Cell parameters from 9524 reflections
b = 14.4877 (10) Å	θ = 2.3–33.2°
c = 16.5149 (12) Å	µ = 0.15 mm^−1
α = 66.858 (2)°	T = 173 K
β = 86.916 (2)°	Block, colourless
γ = 85.396 (2)°	0.45 × 0.40 × 0.35 mm
V = 2801.8 (3) Å^3

Data collection

Bruker SMART CCD diffractometer	11889 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
Graphite monochromator	θmax = 32.5°, θmin = 1.5°
φ and ω scans	h = −19→18
30001 measured reflections	k = −21→21
19380 independent reflections	l = −23→24

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.154	H-atom parameters constrained
S = 0.95	w = 1/[σ^2(Fo^2) + (0.0893P)^2] where P = (Fo^2 + 2Fc^2)/3
19380 reflections	(Δ/σ)max = 0.001
665 parameters	Δρmax = 0.70 e Å^−3
0 restraints	Δρmin = −0.47 e Å^−3

Special details

Experimental. Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
B1	0.14125 (12)	0.68127 (12)	0.03085 (11)	0.0323 (3)
O2	0.06318 (7)	0.62688 (8)	0.02094 (7)	0.0372 (2)
C3	−0.03566 (11)	0.66417 (11)	0.05065 (10)	0.0357 (3)
C4	0.00418 (10)	0.71241 (11)	0.11228 (10)	0.0356 (3)
O5	0.10832 (7)	0.74323 (8)	0.07371 (7)	0.0386 (2)
C6	−0.10372 (13)	0.57574 (13)	0.09626 (13)	0.0498 (4)
H6A	−0.1173	0.5448	0.0550	0.075*
H6B	−0.1705	0.5995	0.1157	0.075*
H6C	−0.0672	0.5260	0.1474	0.075*
C7	−0.08874 (14)	0.74103 (14)	−0.03088 (12)	0.0508 (4)
H7A	−0.0432	0.7966	−0.0600	0.076*
H7B	−0.1557	0.7670	−0.0137	0.076*
H7C	−0.1016	0.7090	−0.0715	0.076*
C8	0.02242 (13)	0.63737 (14)	0.20695 (11)	0.0489 (4)
H8A	0.0674	0.5796	0.2063	0.073*
H8B	−0.0451	0.6144	0.2358	0.073*
H8C	0.0566	0.6701	0.2394	0.073*
C9	−0.06323 (12)	0.80449 (13)	0.11121 (13)	0.0480 (4)
H9A	−0.0397	0.8254	0.1566	0.072*
H9B	−0.1368	0.7879	0.1231	0.072*
H9C	−0.0566	0.8595	0.0533	0.072*
C10	0.25727 (10)	0.67107 (10)	−0.00098 (9)	0.0304 (3)
C11	0.33440 (10)	0.72446 (9)	0.01642 (9)	0.0274 (2)
H11	0.3150	0.7679	0.0462	0.033*
C12	0.43864 (10)	0.71447 (9)	−0.00936 (8)	0.0259 (2)
C13	0.46888 (11)	0.64937 (10)	−0.05117 (9)	0.0327 (3)
H13	0.5403	0.6422	−0.0682	0.039*
C14	0.39358 (12)	0.59475 (11)	−0.06784 (10)	0.0370 (3)
H14	0.4139	0.5497	−0.0958	0.044*
C15	0.28925 (11)	0.60618 (11)	−0.04372 (10)	0.0357 (3)
H15	0.2385	0.5695	−0.0563	0.043*
N16	0.51763 (8)	0.77257 (8)	0.00597 (7)	0.0274 (2)
C17	0.49271 (11)	0.88294 (10)	−0.02315 (10)	0.0348 (3)
H17A	0.5560	0.9157	−0.0186	0.042*
H17B	0.4370	0.8956	0.0160	0.042*
C18	0.45633 (12)	0.92800 (10)	−0.11691 (10)	0.0384 (3)
C19	0.52441 (14)	0.92240 (13)	−0.18480 (12)	0.0494 (4)
C20	0.4885 (2)	0.96409 (16)	−0.27202 (13)	0.0694 (6)
H20	0.5340	0.9608	−0.3184	0.083*
C21	0.3878 (2)	1.00988 (15)	−0.29168 (15)	0.0731 (7)
C22	0.32352 (17)	1.01483 (13)	−0.22404 (15)	0.0644 (6)
H22	0.2551	1.0466	−0.2374	0.077*
C23	0.35412 (13)	0.97539 (11)	−0.13671 (12)	0.0462 (4)
C24	0.63405 (15)	0.87235 (16)	−0.16619 (14)	0.0651 (5)
H24A	0.6697	0.8982	−0.1291	0.098*
H24B	0.6737	0.8870	−0.2218	0.098*
H24C	0.6298	0.7995	−0.1356	0.098*
C25	0.3513 (3)	1.0495 (2)	−0.38704 (16)	0.1133 (12)
H25A	0.2815	1.0266	−0.3881	0.170*
H25B	0.4010	1.0241	−0.4219	0.170*
H25C	0.3482	1.1232	−0.4121	0.170*
C26	0.27535 (14)	0.98581 (13)	−0.06869 (15)	0.0590 (5)
H26A	0.2106	1.0213	−0.0978	0.089*
H26B	0.3046	1.0240	−0.0387	0.089*
H26C	0.2598	0.9189	−0.0255	0.089*
S1	0.58378 (2)	0.71587 (2)	0.09789 (2)	0.02926 (8)
O3	0.61769 (8)	0.61721 (7)	0.10263 (7)	0.0367 (2)
O4	0.65996 (7)	0.78399 (8)	0.09776 (7)	0.0380 (2)
C27	0.49113 (10)	0.70372 (10)	0.18393 (9)	0.0286 (3)
C28	0.47353 (11)	0.77985 (10)	0.21548 (10)	0.0333 (3)
H28	0.5164	0.8355	0.1955	0.040*
C29	0.39218 (12)	0.77331 (11)	0.27682 (10)	0.0387 (3)
H29	0.3803	0.8248	0.2989	0.046*
C30	0.32773 (11)	0.69213 (12)	0.30650 (9)	0.0370 (3)
C31	0.34725 (12)	0.61660 (11)	0.27442 (10)	0.0366 (3)
H31	0.3044	0.5608	0.2945	0.044*
C32	0.42840 (11)	0.62119 (10)	0.21338 (9)	0.0331 (3)
H32	0.4410	0.5691	0.1920	0.040*
C33	0.23807 (14)	0.68650 (15)	0.37209 (12)	0.0524 (4)
H33A	0.1787	0.6568	0.3583	0.079*
H33B	0.2162	0.7544	0.3686	0.079*
H33C	0.2614	0.6447	0.4318	0.079*
B41	0.38932 (12)	0.32720 (11)	0.33425 (11)	0.0306 (3)
O42	0.41170 (8)	0.27175 (9)	0.42095 (7)	0.0436 (3)
C43	0.51416 (11)	0.30026 (12)	0.43611 (11)	0.0396 (3)
C44	0.56476 (11)	0.34166 (12)	0.34137 (11)	0.0397 (3)
O45	0.47209 (7)	0.37786 (7)	0.28548 (7)	0.0373 (2)
C46	0.49194 (17)	0.38018 (18)	0.47444 (16)	0.0711 (6)
H46A	0.4537	0.4390	0.4317	0.107*
H46B	0.5584	0.4002	0.4875	0.107*
H46C	0.4494	0.3528	0.5288	0.107*
C47	0.57327 (13)	0.20790 (14)	0.50099 (12)	0.0541 (5)
H47A	0.5373	0.1868	0.5587	0.081*
H47B	0.6450	0.2241	0.5062	0.081*
H47C	0.5758	0.1533	0.4799	0.081*
C48	0.63457 (15)	0.42870 (16)	0.32180 (16)	0.0736 (7)
H48A	0.6602	0.4517	0.2605	0.110*
H48B	0.6944	0.4063	0.3612	0.110*
H48C	0.5940	0.4842	0.3312	0.110*
C49	0.62164 (14)	0.25964 (16)	0.31660 (13)	0.0628 (5)
H49A	0.5760	0.2039	0.3303	0.094*
H49B	0.6862	0.2351	0.3501	0.094*
H49C	0.6393	0.2871	0.2534	0.094*
C50	0.27959 (10)	0.33402 (9)	0.29480 (9)	0.0282 (3)
C51	0.19536 (10)	0.28411 (10)	0.34882 (9)	0.0280 (3)
H51	0.2058	0.2456	0.4097	0.034*
C52	0.09691 (10)	0.29090 (9)	0.31343 (8)	0.0266 (2)
C53	0.08054 (11)	0.34785 (10)	0.22402 (9)	0.0316 (3)
H53	0.0137	0.3518	0.1999	0.038*
C54	0.16252 (11)	0.39879 (11)	0.17047 (9)	0.0342 (3)
H54	0.1511	0.4387	0.1099	0.041*
C55	0.26116 (11)	0.39148 (10)	0.20524 (9)	0.0318 (3)
H55	0.3168	0.4258	0.1679	0.038*
N56	0.00865 (8)	0.24059 (8)	0.36798 (7)	0.0290 (2)
C57	0.02199 (11)	0.12956 (10)	0.41631 (9)	0.0338 (3)
H57A	−0.0440	0.1044	0.4489	0.041*
H57B	0.0782	0.1132	0.4597	0.041*
C58	0.05001 (11)	0.07761 (10)	0.35348 (9)	0.0321 (3)
C59	0.14733 (11)	0.02270 (10)	0.35927 (10)	0.0365 (3)
C60	0.17181 (13)	−0.02151 (11)	0.29893 (12)	0.0466 (4)
H60	0.2374	−0.0587	0.3031	0.056*
C61	0.10496 (15)	−0.01373 (12)	0.23331 (12)	0.0494 (4)
C62	0.00727 (14)	0.03778 (12)	0.23025 (11)	0.0457 (4)
H62	−0.0409	0.0418	0.1869	0.055*
C63	−0.02180 (11)	0.08367 (11)	0.28926 (10)	0.0370 (3)
C64	0.22829 (12)	0.01101 (12)	0.42726 (12)	0.0476 (4)
H64A	0.2894	−0.0307	0.4200	0.071*
H64B	0.1974	−0.0212	0.4865	0.071*
H64C	0.2503	0.0774	0.4191	0.071*
C65	0.1384 (2)	−0.05698 (18)	0.16480 (17)	0.0803 (7)
H65A	0.2110	−0.0414	0.1452	0.121*
H65B	0.0921	−0.0273	0.1143	0.121*
H65C	0.1336	−0.1301	0.1908	0.121*
C66	−0.12841 (12)	0.14024 (13)	0.28138 (13)	0.0487 (4)
H66A	−0.1202	0.2126	0.2512	0.073*
H66B	−0.1594	0.1260	0.3403	0.073*
H66C	−0.1745	0.1187	0.2475	0.073*
S41	−0.06228 (3)	0.30523 (3)	0.41700 (2)	0.03295 (9)
O43	−0.08324 (8)	0.40487 (8)	0.35193 (7)	0.0422 (2)
O44	−0.14806 (8)	0.24440 (9)	0.46190 (7)	0.0428 (3)
C67	0.01950 (10)	0.31377 (11)	0.49663 (9)	0.0321 (3)
C68	0.07568 (13)	0.39891 (12)	0.47572 (11)	0.0426 (3)
H68	0.0648	0.4550	0.4216	0.051*
C69	0.14836 (14)	0.40100 (14)	0.53539 (12)	0.0493 (4)
H69	0.1868	0.4590	0.5213	0.059*
C70	0.16532 (13)	0.31931 (14)	0.61510 (11)	0.0460 (4)
C71	0.10639 (13)	0.23641 (13)	0.63466 (10)	0.0443 (4)
H71	0.1160	0.1809	0.6894	0.053*
C72	0.03362 (11)	0.23191 (12)	0.57673 (10)	0.0374 (3)
H72	−0.0056	0.1743	0.5915	0.045*
C73	0.24717 (16)	0.32258 (19)	0.67715 (13)	0.0672 (6)
H73A	0.2441	0.2629	0.7323	0.101*
H73B	0.2330	0.3832	0.6896	0.101*
H73C	0.3172	0.3237	0.6496	0.101*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
B1	0.0276 (7)	0.0334 (8)	0.0368 (8)	−0.0103 (6)	0.0022 (6)	−0.0133 (7)
O2	0.0269 (5)	0.0436 (6)	0.0472 (6)	−0.0131 (4)	0.0051 (4)	−0.0230 (5)
C3	0.0248 (6)	0.0418 (8)	0.0420 (8)	−0.0092 (5)	0.0022 (6)	−0.0170 (7)
C4	0.0228 (6)	0.0430 (8)	0.0439 (8)	−0.0066 (5)	0.0026 (6)	−0.0198 (7)
O5	0.0246 (5)	0.0463 (6)	0.0529 (7)	−0.0109 (4)	0.0049 (4)	−0.0270 (5)
C6	0.0323 (8)	0.0518 (10)	0.0666 (12)	−0.0196 (7)	0.0076 (8)	−0.0223 (9)
C7	0.0435 (9)	0.0613 (11)	0.0458 (10)	−0.0052 (8)	−0.0085 (8)	−0.0178 (8)
C8	0.0403 (9)	0.0649 (11)	0.0408 (9)	0.0018 (8)	−0.0011 (7)	−0.0208 (8)
C9	0.0333 (8)	0.0514 (10)	0.0657 (11)	−0.0038 (7)	0.0050 (7)	−0.0302 (9)
C10	0.0275 (6)	0.0309 (6)	0.0325 (7)	−0.0100 (5)	0.0042 (5)	−0.0113 (5)
C11	0.0255 (6)	0.0254 (6)	0.0319 (7)	−0.0059 (5)	0.0038 (5)	−0.0115 (5)
C12	0.0242 (6)	0.0239 (6)	0.0278 (6)	−0.0071 (4)	0.0038 (5)	−0.0076 (5)
C13	0.0305 (7)	0.0344 (7)	0.0345 (7)	−0.0065 (5)	0.0084 (5)	−0.0151 (6)
C14	0.0409 (8)	0.0361 (7)	0.0404 (8)	−0.0093 (6)	0.0075 (6)	−0.0215 (6)
C15	0.0372 (7)	0.0351 (7)	0.0391 (8)	−0.0149 (6)	0.0045 (6)	−0.0173 (6)
N16	0.0248 (5)	0.0253 (5)	0.0310 (6)	−0.0081 (4)	0.0023 (4)	−0.0090 (4)
C17	0.0349 (7)	0.0257 (6)	0.0436 (8)	−0.0095 (5)	−0.0017 (6)	−0.0117 (6)
C18	0.0392 (8)	0.0256 (6)	0.0437 (8)	−0.0142 (6)	−0.0062 (6)	−0.0035 (6)
C19	0.0516 (10)	0.0405 (9)	0.0441 (9)	−0.0243 (7)	0.0032 (8)	−0.0002 (7)
C20	0.0921 (16)	0.0628 (13)	0.0420 (10)	−0.0477 (12)	0.0092 (10)	−0.0015 (9)
C21	0.0901 (16)	0.0505 (11)	0.0564 (12)	−0.0406 (11)	−0.0304 (12)	0.0135 (9)
C22	0.0651 (12)	0.0377 (9)	0.0720 (14)	−0.0196 (8)	−0.0295 (11)	0.0049 (9)
C23	0.0458 (9)	0.0241 (7)	0.0626 (11)	−0.0109 (6)	−0.0139 (8)	−0.0072 (7)
C24	0.0535 (11)	0.0685 (13)	0.0593 (12)	−0.0208 (9)	0.0280 (9)	−0.0105 (10)
C25	0.141 (3)	0.108 (2)	0.0565 (14)	−0.0707 (19)	−0.0401 (16)	0.0215 (14)
C26	0.0422 (9)	0.0366 (9)	0.0967 (16)	0.0047 (7)	−0.0109 (10)	−0.0244 (10)
S1	0.02204 (14)	0.02987 (16)	0.03509 (18)	−0.00359 (11)	0.00137 (12)	−0.01176 (14)
O3	0.0303 (5)	0.0344 (5)	0.0451 (6)	0.0030 (4)	−0.0002 (4)	−0.0162 (5)
O4	0.0244 (5)	0.0436 (6)	0.0467 (6)	−0.0106 (4)	0.0000 (4)	−0.0171 (5)
C27	0.0252 (6)	0.0293 (6)	0.0295 (6)	−0.0007 (5)	−0.0011 (5)	−0.0099 (5)
C28	0.0334 (7)	0.0314 (7)	0.0360 (7)	−0.0045 (5)	−0.0017 (6)	−0.0134 (6)
C29	0.0423 (8)	0.0398 (8)	0.0382 (8)	−0.0006 (6)	0.0016 (6)	−0.0204 (7)
C30	0.0342 (7)	0.0448 (8)	0.0284 (7)	−0.0005 (6)	0.0024 (6)	−0.0112 (6)
C31	0.0362 (7)	0.0329 (7)	0.0347 (7)	−0.0079 (6)	0.0046 (6)	−0.0065 (6)
C32	0.0339 (7)	0.0277 (6)	0.0357 (7)	−0.0040 (5)	0.0035 (6)	−0.0103 (6)
C33	0.0496 (10)	0.0645 (11)	0.0435 (9)	−0.0075 (8)	0.0162 (8)	−0.0230 (9)
B41	0.0248 (7)	0.0279 (7)	0.0349 (8)	−0.0038 (5)	0.0035 (6)	−0.0078 (6)
O42	0.0260 (5)	0.0571 (7)	0.0352 (6)	−0.0101 (5)	0.0006 (4)	−0.0036 (5)
C43	0.0263 (7)	0.0458 (8)	0.0423 (8)	−0.0042 (6)	−0.0021 (6)	−0.0121 (7)
C44	0.0226 (6)	0.0404 (8)	0.0427 (8)	−0.0029 (5)	−0.0027 (6)	−0.0013 (7)
O45	0.0226 (4)	0.0364 (5)	0.0398 (6)	−0.0056 (4)	−0.0003 (4)	−0.0001 (4)
C46	0.0606 (12)	0.0895 (16)	0.0808 (15)	0.0157 (11)	−0.0209 (11)	−0.0535 (14)
C47	0.0380 (8)	0.0606 (11)	0.0454 (10)	−0.0061 (8)	−0.0095 (7)	0.0006 (8)
C48	0.0385 (9)	0.0614 (12)	0.0878 (15)	−0.0237 (9)	−0.0208 (10)	0.0125 (11)
C49	0.0408 (9)	0.0811 (14)	0.0571 (12)	0.0205 (9)	0.0017 (8)	−0.0217 (11)
C50	0.0242 (6)	0.0268 (6)	0.0313 (7)	−0.0050 (5)	0.0040 (5)	−0.0090 (5)
C51	0.0253 (6)	0.0299 (6)	0.0258 (6)	−0.0038 (5)	0.0018 (5)	−0.0075 (5)
C52	0.0242 (6)	0.0287 (6)	0.0249 (6)	−0.0052 (5)	0.0050 (5)	−0.0084 (5)
C53	0.0300 (6)	0.0341 (7)	0.0284 (7)	−0.0049 (5)	−0.0013 (5)	−0.0093 (6)
C54	0.0380 (7)	0.0353 (7)	0.0254 (6)	−0.0086 (6)	0.0029 (5)	−0.0068 (6)
C55	0.0302 (6)	0.0309 (7)	0.0314 (7)	−0.0083 (5)	0.0078 (5)	−0.0090 (6)
N56	0.0241 (5)	0.0337 (6)	0.0276 (5)	−0.0064 (4)	0.0061 (4)	−0.0102 (5)
C57	0.0303 (7)	0.0344 (7)	0.0308 (7)	−0.0077 (5)	0.0063 (5)	−0.0060 (6)
C58	0.0299 (6)	0.0285 (6)	0.0322 (7)	−0.0097 (5)	0.0078 (5)	−0.0053 (5)
C59	0.0325 (7)	0.0269 (6)	0.0413 (8)	−0.0091 (5)	0.0085 (6)	−0.0037 (6)
C60	0.0404 (8)	0.0319 (8)	0.0660 (11)	−0.0101 (6)	0.0172 (8)	−0.0185 (8)
C61	0.0585 (10)	0.0390 (8)	0.0571 (11)	−0.0220 (7)	0.0221 (8)	−0.0251 (8)
C62	0.0531 (10)	0.0429 (9)	0.0449 (9)	−0.0241 (7)	0.0072 (7)	−0.0185 (7)
C63	0.0342 (7)	0.0333 (7)	0.0400 (8)	−0.0128 (6)	0.0050 (6)	−0.0091 (6)
C64	0.0349 (8)	0.0417 (9)	0.0530 (10)	−0.0007 (6)	−0.0008 (7)	−0.0045 (7)
C65	0.0859 (16)	0.0874 (16)	0.0994 (18)	−0.0329 (13)	0.0326 (14)	−0.0696 (15)
C66	0.0352 (8)	0.0538 (10)	0.0596 (11)	−0.0070 (7)	−0.0078 (7)	−0.0230 (9)
S41	0.02245 (15)	0.0435 (2)	0.03243 (18)	−0.00136 (13)	0.00290 (13)	−0.01494 (15)
O43	0.0358 (5)	0.0457 (6)	0.0412 (6)	0.0085 (5)	−0.0042 (5)	−0.0144 (5)
O44	0.0243 (5)	0.0650 (7)	0.0415 (6)	−0.0112 (5)	0.0101 (4)	−0.0231 (6)
C67	0.0265 (6)	0.0402 (7)	0.0303 (7)	−0.0033 (5)	0.0040 (5)	−0.0150 (6)
C68	0.0465 (9)	0.0403 (8)	0.0398 (8)	−0.0072 (7)	0.0011 (7)	−0.0140 (7)
C69	0.0515 (10)	0.0535 (10)	0.0474 (10)	−0.0196 (8)	0.0009 (8)	−0.0217 (8)
C70	0.0369 (8)	0.0700 (11)	0.0367 (8)	−0.0108 (7)	0.0041 (6)	−0.0262 (8)
C71	0.0418 (8)	0.0578 (10)	0.0288 (7)	−0.0066 (7)	0.0020 (6)	−0.0118 (7)
C72	0.0339 (7)	0.0453 (8)	0.0305 (7)	−0.0070 (6)	0.0065 (6)	−0.0121 (6)
C73	0.0519 (11)	0.1100 (17)	0.0458 (11)	−0.0244 (11)	−0.0028 (9)	−0.0329 (11)

Geometric parameters (Å, º)

B1—O2	1.3741 (17)	B41—O45	1.3692 (17)
B1—O5	1.3750 (18)	B41—O42	1.3713 (19)
B1—C10	1.562 (2)	B41—C50	1.558 (2)
O2—C3	1.4699 (17)	O42—C43	1.4667 (17)
C3—C7	1.520 (2)	C43—C47	1.519 (2)
C3—C6	1.522 (2)	C43—C46	1.525 (2)
C3—C4	1.567 (2)	C43—C44	1.563 (2)
C4—O5	1.4687 (16)	C44—O45	1.4721 (17)
C4—C9	1.523 (2)	C44—C49	1.523 (2)
C4—C8	1.531 (2)	C44—C48	1.523 (2)
C6—H6A	0.9800	C46—H46A	0.9800
C6—H6B	0.9800	C46—H46B	0.9800
C6—H6C	0.9800	C46—H46C	0.9800
C7—H7A	0.9800	C47—H47A	0.9800
C7—H7B	0.9800	C47—H47B	0.9800
C7—H7C	0.9800	C47—H47C	0.9800
C8—H8A	0.9800	C48—H48A	0.9800
C8—H8B	0.9800	C48—H48B	0.9800
C8—H8C	0.9800	C48—H48C	0.9800
C9—H9A	0.9800	C49—H49A	0.9800
C9—H9B	0.9800	C49—H49B	0.9800
C9—H9C	0.9800	C49—H49C	0.9800
C10—C15	1.4064 (19)	C50—C55	1.4051 (19)
C10—C11	1.4071 (17)	C50—C51	1.4114 (17)
C11—C12	1.3905 (17)	C51—C52	1.3959 (17)
C11—H11	0.9500	C51—H51	0.9500
C12—C13	1.3929 (17)	C52—C53	1.3974 (18)
C12—N16	1.4571 (15)	C52—N56	1.4565 (16)
C13—C14	1.3963 (19)	C53—C54	1.3913 (19)
C13—H13	0.9500	C53—H53	0.9500
C14—C15	1.387 (2)	C54—C55	1.3924 (19)
C14—H14	0.9500	C54—H54	0.9500
C15—H15	0.9500	C55—H55	0.9500
N16—C17	1.4899 (17)	N56—C57	1.4884 (18)
N16—S1	1.6555 (11)	N56—S41	1.6537 (11)
C17—C18	1.508 (2)	C57—C58	1.5172 (19)
C17—H17A	0.9900	C57—H57A	0.9900
C17—H17B	0.9900	C57—H57B	0.9900
C18—C19	1.406 (3)	C58—C59	1.408 (2)
C18—C23	1.418 (2)	C58—C63	1.412 (2)
C19—C20	1.412 (3)	C59—C60	1.392 (2)
C19—C24	1.514 (3)	C59—C64	1.519 (2)
C20—C21	1.393 (3)	C60—C61	1.380 (3)
C20—H20	0.9500	C60—H60	0.9500
C21—C22	1.372 (3)	C61—C62	1.395 (3)
C21—C25	1.534 (3)	C61—C65	1.522 (2)
C22—C23	1.392 (3)	C62—C63	1.400 (2)
C22—H22	0.9500	C62—H62	0.9500
C23—C26	1.512 (3)	C63—C66	1.517 (2)
C24—H24A	0.9800	C64—H64A	0.9800
C24—H24B	0.9800	C64—H64B	0.9800
C24—H24C	0.9800	C64—H64C	0.9800
C25—H25A	0.9800	C65—H65A	0.9800
C25—H25B	0.9800	C65—H65B	0.9800
C25—H25C	0.9800	C65—H65C	0.9800
C26—H26A	0.9800	C66—H66A	0.9800
C26—H26B	0.9800	C66—H66B	0.9800
C26—H26C	0.9800	C66—H66C	0.9800
S1—O3	1.4328 (10)	S41—O43	1.4354 (11)
S1—O4	1.4402 (10)	S41—O44	1.4430 (11)
S1—C27	1.7629 (14)	S41—C67	1.7701 (14)
C27—C28	1.3921 (18)	C67—C68	1.392 (2)
C27—C32	1.4012 (19)	C67—C72	1.395 (2)
C28—C29	1.394 (2)	C68—C69	1.400 (2)
C28—H28	0.9500	C68—H68	0.9500
C29—C30	1.400 (2)	C69—C70	1.395 (2)
C29—H29	0.9500	C69—H69	0.9500
C30—C31	1.392 (2)	C70—C71	1.389 (2)
C30—C33	1.518 (2)	C70—C73	1.519 (2)
C31—C32	1.394 (2)	C71—C72	1.392 (2)
C31—H31	0.9500	C71—H71	0.9500
C32—H32	0.9500	C72—H72	0.9500
C33—H33A	0.9800	C73—H73A	0.9800
C33—H33B	0.9800	C73—H73B	0.9800
C33—H33C	0.9800	C73—H73C	0.9800
O2—B1—O5	113.71 (12)	O45—B41—O42	113.71 (12)
O2—B1—C10	123.08 (13)	O45—B41—C50	122.82 (13)
O5—B1—C10	123.18 (12)	O42—B41—C50	123.46 (12)
B1—O2—C3	106.96 (11)	B41—O42—C43	106.90 (11)
O2—C3—C7	107.12 (12)	O42—C43—C47	108.78 (13)
O2—C3—C6	108.43 (12)	O42—C43—C46	106.48 (13)
C7—C3—C6	110.65 (13)	C47—C43—C46	110.75 (15)
O2—C3—C4	102.03 (10)	O42—C43—C44	102.37 (12)
C7—C3—C4	112.94 (13)	C47—C43—C44	114.24 (14)
C6—C3—C4	114.94 (13)	C46—C43—C44	113.49 (15)
O5—C4—C9	109.23 (12)	O45—C44—C49	106.22 (13)
O5—C4—C8	106.23 (12)	O45—C44—C48	108.92 (12)
C9—C4—C8	110.70 (13)	C49—C44—C48	110.53 (16)
O5—C4—C3	102.38 (11)	O45—C44—C43	102.31 (11)
C9—C4—C3	113.79 (12)	C49—C44—C43	112.99 (14)
C8—C4—C3	113.82 (12)	C48—C44—C43	115.09 (16)
B1—O5—C4	106.24 (10)	B41—O45—C44	106.82 (11)
C3—C6—H6A	109.5	C43—C46—H46A	109.5
C3—C6—H6B	109.5	C43—C46—H46B	109.5
H6A—C6—H6B	109.5	H46A—C46—H46B	109.5
C3—C6—H6C	109.5	C43—C46—H46C	109.5
H6A—C6—H6C	109.5	H46A—C46—H46C	109.5
H6B—C6—H6C	109.5	H46B—C46—H46C	109.5
C3—C7—H7A	109.5	C43—C47—H47A	109.5
C3—C7—H7B	109.5	C43—C47—H47B	109.5
H7A—C7—H7B	109.5	H47A—C47—H47B	109.5
C3—C7—H7C	109.5	C43—C47—H47C	109.5
H7A—C7—H7C	109.5	H47A—C47—H47C	109.5
H7B—C7—H7C	109.5	H47B—C47—H47C	109.5
C4—C8—H8A	109.5	C44—C48—H48A	109.5
C4—C8—H8B	109.5	C44—C48—H48B	109.5
H8A—C8—H8B	109.5	H48A—C48—H48B	109.5
C4—C8—H8C	109.5	C44—C48—H48C	109.5
H8A—C8—H8C	109.5	H48A—C48—H48C	109.5
H8B—C8—H8C	109.5	H48B—C48—H48C	109.5
C4—C9—H9A	109.5	C44—C49—H49A	109.5
C4—C9—H9B	109.5	C44—C49—H49B	109.5
H9A—C9—H9B	109.5	H49A—C49—H49B	109.5
C4—C9—H9C	109.5	C44—C49—H49C	109.5
H9A—C9—H9C	109.5	H49A—C49—H49C	109.5
H9B—C9—H9C	109.5	H49B—C49—H49C	109.5
C15—C10—C11	117.97 (12)	C55—C50—C51	118.28 (12)
C15—C10—B1	122.08 (12)	C55—C50—B41	121.08 (12)
C11—C10—B1	119.89 (12)	C51—C50—B41	120.62 (12)
C12—C11—C10	120.81 (12)	C52—C51—C50	120.52 (12)
C12—C11—H11	119.6	C52—C51—H51	119.7
C10—C11—H11	119.6	C50—C51—H51	119.7
C11—C12—C13	120.35 (11)	C51—C52—C53	120.24 (12)
C11—C12—N16	120.66 (11)	C51—C52—N56	121.50 (11)
C13—C12—N16	118.99 (11)	C53—C52—N56	118.25 (11)
C12—C13—C14	119.56 (12)	C54—C53—C52	119.73 (12)
C12—C13—H13	120.2	C54—C53—H53	120.1
C14—C13—H13	120.2	C52—C53—H53	120.1
C15—C14—C13	120.12 (13)	C53—C54—C55	120.26 (13)
C15—C14—H14	119.9	C53—C54—H54	119.9
C13—C14—H14	119.9	C55—C54—H54	119.9
C14—C15—C10	121.17 (12)	C54—C55—C50	120.95 (12)
C14—C15—H15	119.4	C54—C55—H55	119.5
C10—C15—H15	119.4	C50—C55—H55	119.5
C12—N16—C17	116.85 (10)	C52—N56—C57	117.37 (10)
C12—N16—S1	115.83 (8)	C52—N56—S41	115.69 (8)
C17—N16—S1	117.06 (9)	C57—N56—S41	117.44 (9)
N16—C17—C18	110.92 (11)	N56—C57—C58	111.09 (11)
N16—C17—H17A	109.5	N56—C57—H57A	109.4
C18—C17—H17A	109.5	C58—C57—H57A	109.4
N16—C17—H17B	109.5	N56—C57—H57B	109.4
C18—C17—H17B	109.5	C58—C57—H57B	109.4
H17A—C17—H17B	108.0	H57A—C57—H57B	108.0
C19—C18—C23	120.05 (15)	C59—C58—C63	119.74 (13)
C19—C18—C17	119.53 (14)	C59—C58—C57	120.22 (13)
C23—C18—C17	120.43 (15)	C63—C58—C57	120.04 (12)
C18—C19—C20	118.67 (18)	C60—C59—C58	118.72 (15)
C18—C19—C24	121.54 (16)	C60—C59—C64	118.14 (14)
C20—C19—C24	119.79 (19)	C58—C59—C64	123.13 (14)
C21—C20—C19	121.5 (2)	C61—C60—C59	122.90 (15)
C21—C20—H20	119.3	C61—C60—H60	118.6
C19—C20—H20	119.3	C59—C60—H60	118.6
C22—C21—C20	118.43 (19)	C60—C61—C62	117.80 (15)
C22—C21—C25	122.4 (2)	C60—C61—C65	120.96 (18)
C20—C21—C25	119.2 (3)	C62—C61—C65	121.20 (19)
C21—C22—C23	122.95 (19)	C61—C62—C63	121.83 (16)
C21—C22—H22	118.5	C61—C62—H62	119.1
C23—C22—H22	118.5	C63—C62—H62	119.1
C22—C23—C18	118.41 (19)	C62—C63—C58	118.93 (14)
C22—C23—C26	117.46 (17)	C62—C63—C66	119.26 (14)
C18—C23—C26	124.13 (16)	C58—C63—C66	121.79 (14)
C19—C24—H24A	109.5	C59—C64—H64A	109.5
C19—C24—H24B	109.5	C59—C64—H64B	109.5
H24A—C24—H24B	109.5	H64A—C64—H64B	109.5
C19—C24—H24C	109.5	C59—C64—H64C	109.5
H24A—C24—H24C	109.5	H64A—C64—H64C	109.5
H24B—C24—H24C	109.5	H64B—C64—H64C	109.5
C21—C25—H25A	109.5	C61—C65—H65A	109.5
C21—C25—H25B	109.5	C61—C65—H65B	109.5
H25A—C25—H25B	109.5	H65A—C65—H65B	109.5
C21—C25—H25C	109.5	C61—C65—H65C	109.5
H25A—C25—H25C	109.5	H65A—C65—H65C	109.5
H25B—C25—H25C	109.5	H65B—C65—H65C	109.5
C23—C26—H26A	109.5	C63—C66—H66A	109.5
C23—C26—H26B	109.5	C63—C66—H66B	109.5
H26A—C26—H26B	109.5	H66A—C66—H66B	109.5
C23—C26—H26C	109.5	C63—C66—H66C	109.5
H26A—C26—H26C	109.5	H66A—C66—H66C	109.5
H26B—C26—H26C	109.5	H66B—C66—H66C	109.5
O3—S1—O4	119.97 (6)	O43—S41—O44	120.07 (7)
O3—S1—N16	107.03 (6)	O43—S41—N56	107.25 (6)
O4—S1—N16	106.59 (6)	O44—S41—N56	106.04 (6)
O3—S1—C27	108.37 (6)	O43—S41—C67	107.92 (7)
O4—S1—C27	108.63 (6)	O44—S41—C67	108.72 (7)
N16—S1—C27	105.32 (6)	N56—S41—C67	106.01 (6)
C28—C27—C32	120.73 (13)	C68—C67—C72	120.67 (13)
C28—C27—S1	120.36 (11)	C68—C67—S41	119.46 (11)
C32—C27—S1	118.59 (10)	C72—C67—S41	119.66 (11)
C27—C28—C29	119.14 (13)	C67—C68—C69	119.24 (15)
C27—C28—H28	120.4	C67—C68—H68	120.4
C29—C28—H28	120.4	C69—C68—H68	120.4
C28—C29—C30	121.16 (13)	C70—C69—C68	121.12 (15)
C28—C29—H29	119.4	C70—C69—H69	119.4
C30—C29—H29	119.4	C68—C69—H69	119.4
C31—C30—C29	118.66 (13)	C71—C70—C69	118.12 (15)
C31—C30—C33	120.52 (15)	C71—C70—C73	122.02 (17)
C29—C30—C33	120.83 (14)	C69—C70—C73	119.85 (17)
C30—C31—C32	121.26 (14)	C70—C71—C72	122.16 (15)
C30—C31—H31	119.4	C70—C71—H71	118.9
C32—C31—H31	119.4	C72—C71—H71	118.9
C31—C32—C27	119.04 (13)	C71—C72—C67	118.66 (14)
C31—C32—H32	120.5	C71—C72—H72	120.7
C27—C32—H32	120.5	C67—C72—H72	120.7
C30—C33—H33A	109.5	C70—C73—H73A	109.5
C30—C33—H33B	109.5	C70—C73—H73B	109.5
H33A—C33—H33B	109.5	H73A—C73—H73B	109.5
C30—C33—H33C	109.5	C70—C73—H73C	109.5
H33A—C33—H33C	109.5	H73A—C73—H73C	109.5
H33B—C33—H33C	109.5	H73B—C73—H73C	109.5