Chiral bis­(mandelato)borate salts for resolution via metathesis crystallization

Spiro­borate anions have potential for crystallization or resolution and chiral bis­(mandelato)borate anions can be used for the efficient resolution of a diverse range of racemic cations via diastereomeric salt formation. The syntheses, X-ray crystal structures and solubilities of three chiral bis­(mandelato)borate salts, namely poly[[aqua-μ₃-bis[(R)-mandelato]borato-lithium(I)] monohydrate], [Li(C₁₆H₁₂BO₆)(H₂O)]_n or Li[B(R-Man)₂]·H₂O, (1), ammonium bis­[(R)-mandel­ato]borate, NH₄⁺·C₁₆H₁₂BO₆⁻ or NH₄[B(R-Man)₂], (2), and tetra-n-butyl­am­mo­nium bis­[(R)-mandelato]borate, C₁₆H₃₆N⁺·C₁₆H₁₂BO₆⁻ or NBu₄[B(R-Man)₂], (3), are reported. They all have a B_S configuration and show a reasonably well-conserved anion geometry. The main conformational variation is the orientation of the two phenyl groups, supporting the idea that [B(Man)₂]⁻ is a semi-rigid anion. The salts are differentially soluble in a range of solvents, meaning they could be useful as reagents for resolution via a metathesis crystallization approach.

Computing details

Data collection: CrysAlis PRO (Oxford Diffraction, 2009) for jack323a, jack315cult; CrysAlis PRO (Rigaku OD, 2015) for jack336a. Cell refinement: CrysAlis PRO (Oxford Diffraction, 2009) for jack323a, jack315cult; CrysAlis PRO (Rigaku OD, 2015) for jack336a. Data reduction: CrysAlis PRO (Oxford Diffraction, 2009) for jack323a, jack315cult; CrysAlis PRO (Rigaku OD, 2015) for jack336a. For all structures, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Poly[[aqua-µ₃-bis[(R)-mandelato]borato-lithium(I)] monohydrate] (jack323a)

Crystal data

[Li(C16H12BO6)(H2O)]	F(000) = 348
Mr = 336.02	Dx = 1.361 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54178 Å
a = 6.5592 (1) Å	Cell parameters from 4712 reflections
b = 9.1328 (2) Å	θ = 4.8–71.5°
c = 13.7163 (3) Å	µ = 0.88 mm^−1
β = 93.900 (2)°	T = 173 K
V = 819.76 (3) Å^3	Plate, colourless
Z = 2	0.3 × 0.12 × 0.04 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 Gemini ultra diffractometer	3072 independent reflections
Radiation source: sealed X-ray tube	2973 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.016
Detector resolution: 15.9578 pixels mm^-1	θmax = 71.5°, θmin = 5.8°
ω scans	h = −8→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −11→11
Tmin = 0.933, Tmax = 1.000	l = −16→16
5234 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.030	w = 1/[σ^2(Fo^2) + (0.054P)^2 + 0.079P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.082	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.20 e Å^−3
3072 reflections	Δρmin = −0.16 e Å^−3
234 parameters	Absolute structure: Flack x determined using 1336 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.00 (12)
Primary atom site location: structure-invariant direct methods

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.

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

	x	y	z	Uiso*/Ueq
Li1	−0.0036 (5)	0.4996 (4)	0.5805 (3)	0.0340 (7)
O1W	−0.0466 (3)	0.6672 (2)	0.66410 (17)	0.0483 (4)
B1	0.2474 (3)	0.5397 (2)	0.41033 (16)	0.0273 (4)
O10	0.7637 (2)	0.49959 (18)	0.48259 (11)	0.0352 (3)
O11	0.47179 (19)	0.54561 (16)	0.39532 (10)	0.0297 (3)
C11	0.5786 (3)	0.4969 (2)	0.47287 (14)	0.0269 (4)
O12	0.23557 (19)	0.46606 (16)	0.50320 (10)	0.0284 (3)
C12	0.4344 (3)	0.4376 (2)	0.54731 (14)	0.0266 (4)
H12	0.4544	0.3295	0.5546	0.032*
C13	0.4728 (3)	0.5104 (2)	0.64566 (14)	0.0298 (4)
C14	0.5576 (3)	0.4314 (3)	0.72492 (16)	0.0404 (5)
H14	0.5859	0.3300	0.7183	0.048*
C15	0.6009 (4)	0.5016 (4)	0.81406 (18)	0.0549 (7)
H15	0.6608	0.4484	0.8682	0.066*
C16	0.5567 (5)	0.6488 (4)	0.82375 (19)	0.0569 (7)
H16	0.5875	0.6965	0.8845	0.068*
C17	0.4683 (4)	0.7264 (3)	0.74596 (19)	0.0482 (6)
H17	0.4352	0.8269	0.7534	0.058*
C18	0.4277 (3)	0.6577 (3)	0.65660 (16)	0.0359 (5)
H18	0.3686	0.7117	0.6026	0.043*
O20	−0.0524 (2)	0.83500 (17)	0.32964 (11)	0.0352 (3)
O21	0.1715 (2)	0.69350 (15)	0.41542 (9)	0.0286 (3)
C21	0.0315 (3)	0.7180 (2)	0.34423 (14)	0.0279 (4)
O22	0.1281 (2)	0.47416 (15)	0.33006 (10)	0.0302 (3)
C22	−0.0011 (3)	0.5804 (2)	0.28236 (14)	0.0298 (4)
H22	−0.1467	0.5482	0.2828	0.036*
C23	0.0514 (3)	0.6111 (3)	0.17801 (15)	0.0356 (5)
C24	−0.0785 (5)	0.6976 (4)	0.1179 (2)	0.0590 (8)
H24	−0.2028	0.7329	0.1409	0.071*
C25	−0.0266 (6)	0.7324 (5)	0.0243 (2)	0.0748 (10)
H25	−0.1141	0.7931	−0.0162	0.090*
C26	0.1512 (6)	0.6794 (5)	−0.0101 (2)	0.0740 (10)
H26	0.1828	0.6991	−0.0754	0.089*
C27	0.2825 (6)	0.5983 (5)	0.0499 (2)	0.0736 (10)
H27	0.4080	0.5653	0.0269	0.088*
C28	0.2332 (5)	0.5637 (3)	0.14472 (19)	0.0528 (7)
H28	0.3251	0.5075	0.1861	0.063*
H1WA	−0.070 (6)	0.759 (6)	0.647 (3)	0.077 (12)*
H1WB	−0.135 (12)	0.650 (9)	0.705 (5)	0.18 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Li1	0.0258 (15)	0.0407 (19)	0.0357 (17)	0.0001 (14)	0.0036 (13)	0.0032 (15)
O1W	0.0363 (9)	0.0363 (9)	0.0728 (12)	0.0001 (7)	0.0086 (8)	−0.0037 (8)
B1	0.0232 (10)	0.0296 (11)	0.0290 (10)	0.0000 (8)	0.0021 (8)	−0.0004 (8)
O10	0.0215 (6)	0.0454 (9)	0.0390 (8)	0.0023 (6)	0.0045 (5)	0.0047 (7)
O11	0.0236 (7)	0.0372 (8)	0.0285 (7)	0.0007 (5)	0.0033 (5)	0.0042 (6)
C11	0.0242 (9)	0.0274 (9)	0.0295 (9)	0.0018 (7)	0.0041 (7)	−0.0002 (7)
O12	0.0192 (6)	0.0362 (7)	0.0297 (6)	−0.0009 (5)	0.0004 (5)	0.0052 (5)
C12	0.0191 (9)	0.0302 (10)	0.0306 (9)	0.0009 (7)	0.0018 (7)	0.0045 (7)
C13	0.0194 (8)	0.0399 (11)	0.0303 (10)	−0.0015 (7)	0.0041 (7)	0.0030 (8)
C14	0.0337 (11)	0.0543 (14)	0.0331 (10)	0.0034 (9)	0.0019 (8)	0.0072 (10)
C15	0.0480 (14)	0.085 (2)	0.0305 (12)	−0.0026 (14)	−0.0041 (10)	0.0072 (12)
C16	0.0537 (15)	0.080 (2)	0.0369 (13)	−0.0147 (14)	0.0029 (11)	−0.0148 (13)
C17	0.0443 (13)	0.0515 (14)	0.0495 (13)	−0.0113 (12)	0.0097 (10)	−0.0141 (12)
C18	0.0303 (10)	0.0405 (12)	0.0371 (11)	−0.0056 (9)	0.0034 (8)	−0.0021 (9)
O20	0.0321 (7)	0.0365 (8)	0.0365 (8)	0.0091 (6)	−0.0005 (6)	−0.0037 (6)
O21	0.0263 (7)	0.0298 (8)	0.0290 (6)	0.0013 (5)	−0.0029 (5)	−0.0023 (5)
C21	0.0230 (9)	0.0325 (10)	0.0283 (8)	0.0016 (7)	0.0023 (7)	−0.0008 (8)
O22	0.0319 (7)	0.0271 (7)	0.0307 (7)	0.0020 (6)	−0.0035 (5)	−0.0028 (5)
C22	0.0261 (9)	0.0312 (10)	0.0313 (10)	0.0017 (7)	−0.0036 (7)	−0.0031 (8)
C23	0.0389 (11)	0.0395 (11)	0.0275 (9)	−0.0013 (8)	−0.0050 (8)	−0.0065 (8)
C24	0.0480 (14)	0.087 (2)	0.0405 (13)	0.0131 (14)	−0.0109 (11)	0.0067 (13)
C25	0.078 (2)	0.102 (3)	0.0411 (14)	0.008 (2)	−0.0206 (14)	0.0172 (17)
C26	0.093 (3)	0.098 (3)	0.0311 (12)	0.001 (2)	0.0051 (14)	0.0040 (15)
C27	0.089 (2)	0.087 (2)	0.0475 (15)	0.024 (2)	0.0276 (16)	0.0083 (16)
C28	0.0613 (16)	0.0580 (16)	0.0400 (13)	0.0195 (13)	0.0109 (11)	0.0050 (11)

Geometric parameters (Å, º)

Li1—O1W	1.945 (4)	C16—H16	0.9500
Li1—O10^i	1.963 (4)	C16—C17	1.376 (4)
Li1—O12	1.976 (4)	C17—H17	0.9500
Li1—O20^ii	1.963 (4)	C17—C18	1.387 (3)
Li1—C21^ii	2.783 (4)	C18—H18	0.9500
O1W—H1WA	0.88 (5)	O20—Li1^iv	1.963 (4)
O1W—H1WB	0.84 (8)	O20—C21	1.212 (3)
B1—O11	1.501 (2)	O21—C21	1.313 (2)
B1—O12	1.447 (3)	C21—Li1^iv	2.783 (4)
B1—O21	1.494 (3)	C21—C22	1.523 (3)
B1—O22	1.437 (3)	O22—C22	1.419 (2)
O10—Li1^iii	1.963 (4)	C22—H22	1.0000
O10—C11	1.212 (2)	C22—C23	1.521 (3)
O11—C11	1.311 (2)	C23—C24	1.391 (4)
C11—C12	1.537 (2)	C23—C28	1.376 (4)
O12—C12	1.424 (2)	C24—H24	0.9500
C12—H12	1.0000	C24—C25	1.387 (4)
C12—C13	1.510 (3)	C25—H25	0.9500
C13—C14	1.389 (3)	C25—C26	1.375 (6)
C13—C18	1.388 (3)	C26—H26	0.9500
C14—H14	0.9500	C26—C27	1.368 (5)
C14—C15	1.392 (4)	C27—H27	0.9500
C15—H15	0.9500	C27—C28	1.398 (4)
C15—C16	1.384 (5)	C28—H28	0.9500
O1W—Li1—O10^i	105.43 (18)	C15—C16—H16	119.8
O1W—Li1—O12	126.2 (2)	C17—C16—C15	120.4 (2)
O1W—Li1—O20^ii	105.10 (18)	C17—C16—H16	119.8
O1W—Li1—C21^ii	119.51 (17)	C16—C17—H17	120.1
O10^i—Li1—O12	104.00 (17)	C16—C17—C18	119.9 (3)
O10^i—Li1—C21^ii	100.72 (16)	C18—C17—H17	120.1
O12—Li1—C21^ii	97.49 (15)	C13—C18—H18	119.8
O20^ii—Li1—O10^i	122.2 (2)	C17—C18—C13	120.3 (2)
O20^ii—Li1—O12	95.56 (17)	C17—C18—H18	119.8
O20^ii—Li1—C21^ii	22.04 (8)	C21—O20—Li1^iv	120.54 (17)
Li1—O1W—H1WA	129 (3)	C21—O21—B1	110.11 (15)
Li1—O1W—H1WB	112 (6)	O20—C21—Li1^iv	37.42 (12)
H1WA—O1W—H1WB	104 (6)	O20—C21—O21	123.99 (19)
O12—B1—O11	104.45 (15)	O20—C21—C22	126.19 (17)
O12—B1—O21	110.95 (16)	O21—C21—Li1^iv	86.65 (13)
O21—B1—O11	107.79 (15)	O21—C21—C22	109.78 (17)
O22—B1—O11	113.46 (16)	C22—C21—Li1^iv	163.57 (15)
O22—B1—O12	114.96 (17)	C22—O22—B1	110.23 (15)
O22—B1—O21	105.15 (15)	C21—C22—H22	109.7
C11—O10—Li1^iii	143.27 (17)	O22—C22—C21	104.51 (15)
C11—O11—B1	110.58 (14)	O22—C22—H22	109.7
O10—C11—O11	123.94 (18)	O22—C22—C23	113.21 (17)
O10—C11—C12	126.22 (18)	C23—C22—C21	109.89 (18)
O11—C11—C12	109.84 (15)	C23—C22—H22	109.7
B1—O12—Li1	119.50 (15)	C24—C23—C22	119.6 (2)
C12—O12—Li1	122.55 (15)	C28—C23—C22	120.7 (2)
C12—O12—B1	110.87 (14)	C28—C23—C24	119.5 (2)
C11—C12—H12	109.4	C23—C24—H24	120.0
O12—C12—C11	103.93 (14)	C25—C24—C23	120.0 (3)
O12—C12—H12	109.4	C25—C24—H24	120.0
O12—C12—C13	113.06 (16)	C24—C25—H25	119.9
C13—C12—C11	111.45 (16)	C26—C25—C24	120.3 (3)
C13—C12—H12	109.4	C26—C25—H25	119.9
C14—C13—C12	120.3 (2)	C25—C26—H26	120.1
C18—C13—C12	119.98 (18)	C27—C26—C25	119.9 (3)
C18—C13—C14	119.7 (2)	C27—C26—H26	120.1
C13—C14—H14	120.2	C26—C27—H27	119.8
C13—C14—C15	119.7 (3)	C26—C27—C28	120.4 (3)
C15—C14—H14	120.2	C28—C27—H27	119.8
C14—C15—H15	120.0	C23—C28—C27	119.9 (3)
C16—C15—C14	120.0 (3)	C23—C28—H28	120.1
C16—C15—H15	120.0	C27—C28—H28	120.1
Li1^iii—O10—C11—O11	156.5 (3)	C12—C13—C14—C15	177.0 (2)
Li1^iii—O10—C11—C12	−23.4 (4)	C12—C13—C18—C17	−178.0 (2)
Li1—O12—C12—C11	−151.52 (18)	C13—C14—C15—C16	1.0 (4)
Li1—O12—C12—C13	−30.5 (3)	C14—C13—C18—C17	0.5 (3)
Li1^iv—O20—C21—O21	−4.1 (3)	C14—C15—C16—C17	0.6 (4)
Li1^iv—O20—C21—C22	178.40 (19)	C15—C16—C17—C18	−1.5 (4)
Li1^iv—C21—C22—O22	−175.7 (5)	C16—C17—C18—C13	1.0 (4)
Li1^iv—C21—C22—C23	62.5 (6)	C18—C13—C14—C15	−1.5 (3)
B1—O11—C11—O10	−174.60 (19)	O20—C21—C22—O22	−179.14 (19)
B1—O11—C11—C12	5.4 (2)	O20—C21—C22—C23	59.1 (3)
B1—O12—C12—C11	−1.2 (2)	O21—B1—O11—C11	112.09 (17)
B1—O12—C12—C13	119.77 (18)	O21—B1—O12—Li1	39.6 (2)
B1—O21—C21—Li1^iv	179.38 (14)	O21—B1—O12—C12	−111.73 (17)
B1—O21—C21—O20	−178.10 (19)	O21—B1—O22—C22	4.7 (2)
B1—O21—C21—C22	−0.3 (2)	O21—C21—C22—O22	3.1 (2)
B1—O22—C22—C21	−4.8 (2)	O21—C21—C22—C23	−118.67 (17)
B1—O22—C22—C23	114.80 (18)	C21—C22—C23—C24	−72.2 (3)
O10—C11—C12—O12	177.3 (2)	C21—C22—C23—C28	102.8 (3)
O10—C11—C12—C13	55.2 (3)	O22—B1—O11—C11	−131.91 (17)
O11—B1—O12—Li1	155.47 (17)	O22—B1—O12—Li1	−79.5 (2)
O11—B1—O12—C12	4.2 (2)	O22—B1—O12—C12	129.14 (17)
O11—B1—O21—C21	118.71 (16)	O22—B1—O21—C21	−2.6 (2)
O11—B1—O22—C22	−112.89 (18)	O22—C22—C23—C24	171.3 (2)
O11—C11—C12—O12	−2.7 (2)	O22—C22—C23—C28	−13.6 (3)
O11—C11—C12—C13	−124.75 (17)	C22—C23—C24—C25	176.7 (3)
C11—C12—C13—C14	−110.9 (2)	C22—C23—C28—C27	−177.3 (3)
C11—C12—C13—C18	67.6 (2)	C23—C24—C25—C26	1.3 (6)
O12—B1—O11—C11	−6.0 (2)	C24—C23—C28—C27	−2.3 (5)
O12—B1—O21—C21	−127.50 (16)	C24—C25—C26—C27	−3.4 (7)
O12—B1—O22—C22	126.98 (17)	C25—C26—C27—C28	2.7 (7)
O12—C12—C13—C14	132.4 (2)	C26—C27—C28—C23	0.1 (6)
O12—C12—C13—C18	−49.0 (2)	C28—C23—C24—C25	1.6 (5)

Symmetry codes: (i) x−1, y, z; (ii) −x, y−1/2, −z+1; (iii) x+1, y, z; (iv) −x, y+1/2, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O22^iv	0.88 (5)	2.03 (5)	2.856 (2)	156 (4)

Symmetry code: (iv) −x, y+1/2, −z+1.

Ammonium bis[(R)-mandelato]borate (jack336a)

Crystal data

NH4^+·C16H12BO6^−	F(000) = 344
Mr = 329.11	Dx = 1.335 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54178 Å
a = 7.49015 (16) Å	Cell parameters from 2730 reflections
b = 8.24219 (13) Å	θ = 5.9–75.3°
c = 13.2750 (3) Å	µ = 0.85 mm^−1
β = 92.8753 (19)°	T = 173 K
V = 818.50 (3) Å^3	Needle, colourless
Z = 2	0.15 × 0.05 × 0.02 mm

Data collection

Rigaku SuperNova Dual Source diffractometer with an Atlas detector	3190 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	3075 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.017
Detector resolution: 10.3577 pixels mm^-1	θmax = 75.5°, θmin = 3.3°
ω scans	h = −6→9
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −10→9
Tmin = 0.923, Tmax = 1.000	l = −16→15
4618 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.026	w = 1/[σ^2(Fo^2) + (0.032P)^2 + 0.044P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.065	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.14 e Å^−3
3190 reflections	Δρmin = −0.14 e Å^−3
233 parameters	Absolute structure: Flack x determined using 1334 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: −0.12 (8)
Primary atom site location: structure-invariant direct methods

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.

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

	x	y	z	Uiso*/Ueq
N1	0.4166 (2)	0.24973 (19)	0.62964 (13)	0.0272 (3)
B1	0.2998 (3)	0.7049 (2)	0.59305 (15)	0.0253 (4)
O10	0.5606 (2)	0.96849 (17)	0.74092 (11)	0.0386 (3)
O11	0.38354 (17)	0.86462 (15)	0.61639 (10)	0.0282 (3)
O12	0.39179 (17)	0.59172 (15)	0.66107 (9)	0.0271 (3)
O20	−0.15444 (17)	0.67760 (19)	0.52404 (11)	0.0351 (3)
O21	0.10379 (17)	0.71721 (16)	0.61159 (9)	0.0278 (3)
O22	0.30353 (16)	0.66262 (17)	0.48749 (9)	0.0288 (3)
C11	0.4880 (2)	0.8539 (2)	0.69955 (13)	0.0268 (4)
C12	0.4971 (2)	0.6776 (2)	0.73532 (13)	0.0256 (3)
H12	0.6235	0.6386	0.7354	0.031*
C13	0.4279 (2)	0.6588 (2)	0.83989 (13)	0.0267 (4)
C14	0.2647 (3)	0.7265 (2)	0.86272 (14)	0.0301 (4)
H14	0.1968	0.7847	0.8123	0.036*
C15	0.2000 (3)	0.7100 (3)	0.95829 (16)	0.0370 (4)
H15	0.0890	0.7578	0.9734	0.044*
C16	0.2981 (3)	0.6234 (3)	1.03194 (16)	0.0416 (5)
H16	0.2547	0.6124	1.0976	0.050*
C17	0.4583 (3)	0.5536 (3)	1.00933 (16)	0.0457 (5)
H17	0.5242	0.4927	1.0593	0.055*
C18	0.5244 (3)	0.5716 (3)	0.91382 (15)	0.0377 (4)
H18	0.6357	0.5241	0.8991	0.045*
C21	0.0083 (2)	0.6726 (2)	0.53122 (14)	0.0260 (3)
C22	0.1304 (2)	0.6159 (2)	0.44963 (13)	0.0254 (4)
H22	0.1249	0.4949	0.4446	0.030*
C23	0.0747 (2)	0.6887 (2)	0.34828 (13)	0.0250 (3)
C24	0.1070 (3)	0.8516 (2)	0.32750 (14)	0.0302 (4)
H24	0.1786	0.9151	0.3736	0.036*
C25	0.0345 (3)	0.9209 (3)	0.23931 (17)	0.0345 (4)
H25	0.0558	1.0321	0.2255	0.041*
C26	−0.0691 (3)	0.8284 (3)	0.17121 (14)	0.0351 (4)
H26	−0.1208	0.8768	0.1117	0.042*
C27	−0.0964 (3)	0.6655 (3)	0.19051 (15)	0.0365 (4)
H27	−0.1649	0.6014	0.1433	0.044*
C28	−0.0241 (3)	0.5952 (2)	0.27869 (14)	0.0313 (4)
H28	−0.0423	0.4831	0.2913	0.038*
H1A	0.406 (4)	0.357 (4)	0.645 (2)	0.043 (7)*
H1B	0.518 (4)	0.237 (4)	0.589 (2)	0.043 (7)*
H1C	0.445 (4)	0.189 (4)	0.686 (2)	0.049 (8)*
H1D	0.320 (4)	0.221 (4)	0.591 (2)	0.045 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0270 (8)	0.0225 (8)	0.0319 (8)	−0.0001 (6)	−0.0003 (6)	−0.0031 (6)
B1	0.0266 (9)	0.0220 (9)	0.0271 (9)	−0.0006 (7)	−0.0005 (7)	−0.0006 (7)
O10	0.0537 (9)	0.0280 (7)	0.0330 (7)	−0.0128 (6)	−0.0088 (6)	0.0014 (6)
O11	0.0345 (7)	0.0231 (6)	0.0263 (6)	−0.0043 (5)	−0.0054 (5)	0.0033 (5)
O12	0.0341 (7)	0.0199 (5)	0.0264 (6)	0.0017 (5)	−0.0066 (5)	−0.0023 (5)
O20	0.0256 (6)	0.0418 (8)	0.0377 (7)	−0.0010 (6)	−0.0004 (5)	0.0099 (6)
O21	0.0284 (6)	0.0288 (6)	0.0261 (6)	0.0021 (5)	0.0012 (5)	−0.0005 (5)
O22	0.0235 (6)	0.0384 (7)	0.0241 (6)	−0.0001 (5)	−0.0021 (5)	−0.0047 (5)
C11	0.0324 (9)	0.0237 (8)	0.0241 (8)	−0.0032 (7)	−0.0008 (7)	0.0016 (7)
C12	0.0273 (8)	0.0225 (8)	0.0264 (8)	0.0009 (7)	−0.0042 (6)	−0.0010 (7)
C13	0.0325 (9)	0.0197 (7)	0.0271 (8)	−0.0014 (7)	−0.0049 (7)	0.0011 (6)
C14	0.0362 (9)	0.0264 (8)	0.0273 (9)	0.0038 (7)	−0.0031 (7)	0.0030 (7)
C15	0.0412 (10)	0.0377 (10)	0.0321 (10)	0.0026 (8)	0.0026 (8)	−0.0007 (8)
C16	0.0503 (12)	0.0482 (12)	0.0260 (9)	−0.0042 (10)	−0.0001 (8)	0.0056 (8)
C17	0.0507 (13)	0.0529 (13)	0.0325 (10)	0.0068 (10)	−0.0074 (9)	0.0164 (10)
C18	0.0377 (10)	0.0401 (11)	0.0347 (10)	0.0073 (9)	−0.0041 (8)	0.0102 (9)
C21	0.0267 (8)	0.0220 (7)	0.0293 (8)	−0.0016 (6)	0.0001 (6)	0.0045 (6)
C22	0.0262 (8)	0.0225 (8)	0.0271 (8)	−0.0001 (6)	−0.0037 (7)	−0.0024 (6)
C23	0.0248 (8)	0.0255 (9)	0.0246 (8)	0.0016 (7)	0.0000 (6)	−0.0020 (7)
C24	0.0334 (9)	0.0247 (9)	0.0320 (9)	−0.0002 (7)	−0.0029 (7)	−0.0037 (7)
C25	0.0382 (10)	0.0280 (9)	0.0375 (11)	0.0052 (7)	0.0023 (8)	0.0043 (7)
C26	0.0355 (10)	0.0430 (11)	0.0267 (9)	0.0082 (8)	0.0003 (7)	0.0033 (8)
C27	0.0386 (10)	0.0442 (11)	0.0259 (8)	−0.0045 (9)	−0.0052 (7)	−0.0052 (8)
C28	0.0359 (10)	0.0296 (9)	0.0280 (9)	−0.0060 (8)	−0.0017 (7)	−0.0023 (7)

Geometric parameters (Å, º)

N1—H1A	0.92 (3)	C15—H15	0.9500
N1—H1B	0.96 (3)	C15—C16	1.391 (3)
N1—H1C	0.91 (3)	C16—H16	0.9500
N1—H1D	0.89 (3)	C16—C17	1.378 (4)
B1—O11	1.484 (2)	C17—H17	0.9500
B1—O12	1.448 (2)	C17—C18	1.392 (3)
B1—O21	1.504 (2)	C18—H18	0.9500
B1—O22	1.446 (2)	C21—C22	1.526 (3)
O10—C11	1.208 (2)	C22—H22	1.0000
O11—C11	1.323 (2)	C22—C23	1.513 (2)
O12—C12	1.420 (2)	C23—C24	1.394 (3)
O20—C21	1.218 (2)	C23—C28	1.388 (3)
O21—C21	1.307 (2)	C24—H24	0.9500
O22—C22	1.420 (2)	C24—C25	1.389 (3)
C11—C12	1.529 (2)	C25—H25	0.9500
C12—H12	1.0000	C25—C26	1.389 (3)
C12—C13	1.514 (3)	C26—H26	0.9500
C13—C14	1.391 (3)	C26—C27	1.384 (3)
C13—C18	1.390 (2)	C27—H27	0.9500
C14—H14	0.9500	C27—C28	1.391 (3)
C14—C15	1.387 (3)	C28—H28	0.9500
H1A—N1—H1B	108 (3)	C17—C16—C15	119.8 (2)
H1A—N1—H1C	111 (3)	C17—C16—H16	120.1
H1A—N1—H1D	108 (2)	C16—C17—H17	119.8
H1B—N1—H1C	104 (2)	C16—C17—C18	120.50 (19)
H1B—N1—H1D	107 (2)	C18—C17—H17	119.8
H1C—N1—H1D	118 (3)	C13—C18—C17	120.1 (2)
O11—B1—O21	108.15 (14)	C13—C18—H18	119.9
O12—B1—O11	104.96 (14)	C17—C18—H18	119.9
O12—B1—O21	112.29 (15)	O20—C21—O21	123.96 (17)
O22—B1—O11	112.80 (15)	O20—C21—C22	126.02 (17)
O22—B1—O12	114.68 (15)	O21—C21—C22	110.02 (14)
O22—B1—O21	103.97 (14)	O22—C22—C21	103.60 (14)
C11—O11—B1	109.94 (14)	O22—C22—H22	109.1
C12—O12—B1	110.00 (13)	O22—C22—C23	114.44 (15)
C21—O21—B1	110.25 (14)	C21—C22—H22	109.1
C22—O22—B1	110.29 (14)	C23—C22—C21	111.17 (14)
O10—C11—O11	124.13 (17)	C23—C22—H22	109.1
O10—C11—C12	126.13 (16)	C24—C23—C22	120.99 (16)
O11—C11—C12	109.72 (14)	C28—C23—C22	119.09 (16)
O12—C12—C11	104.10 (13)	C28—C23—C24	119.67 (17)
O12—C12—H12	109.5	C23—C24—H24	120.1
O12—C12—C13	112.44 (15)	C25—C24—C23	119.88 (18)
C11—C12—H12	109.5	C25—C24—H24	120.1
C13—C12—C11	111.71 (15)	C24—C25—H25	119.8
C13—C12—H12	109.5	C24—C25—C26	120.4 (2)
C14—C13—C12	120.25 (16)	C26—C25—H25	119.8
C18—C13—C12	120.72 (17)	C25—C26—H26	120.2
C18—C13—C14	119.02 (18)	C27—C26—C25	119.64 (18)
C13—C14—H14	119.6	C27—C26—H26	120.2
C15—C14—C13	120.77 (18)	C26—C27—H27	119.8
C15—C14—H14	119.6	C26—C27—C28	120.31 (19)
C14—C15—H15	120.1	C28—C27—H27	119.8
C14—C15—C16	119.8 (2)	C23—C28—C27	120.07 (19)
C16—C15—H15	120.1	C23—C28—H28	120.0
C15—C16—H16	120.1	C27—C28—H28	120.0
B1—O11—C11—O10	−173.32 (18)	O21—C21—C22—C23	−133.76 (15)
B1—O11—C11—C12	5.2 (2)	O22—B1—O11—C11	−135.78 (16)
B1—O12—C12—C11	−8.54 (18)	O22—B1—O12—C12	135.88 (16)
B1—O12—C12—C13	112.55 (17)	O22—B1—O21—C21	5.59 (18)
B1—O21—C21—O20	−176.66 (18)	O22—C22—C23—C24	−43.2 (2)
B1—O21—C21—C22	2.90 (19)	O22—C22—C23—C28	142.58 (17)
B1—O22—C22—C21	13.94 (18)	C11—C12—C13—C14	49.1 (2)
B1—O22—C22—C23	135.14 (16)	C11—C12—C13—C18	−132.11 (19)
O10—C11—C12—O12	−179.55 (19)	C12—C13—C14—C15	179.98 (18)
O10—C11—C12—C13	58.9 (3)	C12—C13—C18—C17	−179.2 (2)
O11—B1—O12—C12	11.54 (19)	C13—C14—C15—C16	−0.7 (3)
O11—B1—O21—C21	125.71 (15)	C14—C13—C18—C17	−0.4 (3)
O11—B1—O22—C22	−129.40 (15)	C14—C15—C16—C17	−0.4 (3)
O11—C11—C12—O12	2.0 (2)	C15—C16—C17—C18	1.2 (4)
O11—C11—C12—C13	−119.59 (16)	C16—C17—C18—C13	−0.7 (4)
O12—B1—O11—C11	−10.3 (2)	C18—C13—C14—C15	1.1 (3)
O12—B1—O21—C21	−118.95 (16)	C21—C22—C23—C24	73.7 (2)
O12—B1—O22—C22	110.51 (17)	C21—C22—C23—C28	−100.49 (19)
O12—C12—C13—C14	−67.6 (2)	C22—C23—C24—C25	−171.65 (18)
O12—C12—C13—C18	111.27 (19)	C22—C23—C28—C27	171.71 (18)
O20—C21—C22—O22	169.16 (18)	C23—C24—C25—C26	−0.5 (3)
O20—C21—C22—C23	45.8 (2)	C24—C23—C28—C27	−2.6 (3)
O21—B1—O11—C11	109.80 (16)	C24—C25—C26—C27	−1.5 (3)
O21—B1—O12—C12	−105.73 (16)	C25—C26—C27—C28	1.4 (3)
O21—B1—O22—C22	−12.48 (18)	C26—C27—C28—C23	0.6 (3)
O21—C21—C22—O22	−10.39 (19)	C28—C23—C24—C25	2.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O12	0.92 (3)	1.95 (3)	2.857 (2)	173 (3)
N1—H1B···O22^i	0.96 (3)	1.82 (3)	2.767 (2)	167 (3)
N1—H1C···O10^ii	0.91 (3)	2.13 (3)	2.926 (2)	145 (3)
N1—H1D···O20^iii	0.89 (3)	1.96 (3)	2.823 (2)	163 (3)

Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) x, y−1, z; (iii) −x, y−1/2, −z+1.

Tetra-n-butylammonium bis[(R)-mandelato]borate (jack315cult)

Crystal data

C16H36N^+·C16H12BO6^−	Dx = 1.172 Mg m^−3
Mr = 553.52	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P212121	Cell parameters from 8149 reflections
a = 9.0372 (6) Å	θ = 3.0–71.4°
b = 15.5934 (6) Å	µ = 0.63 mm^−1
c = 44.5357 (11) Å	T = 173 K
V = 6276.0 (5) Å^3	Block, colourless
Z = 8	0.35 × 0.30 × 0.22 mm
F(000) = 2400

Data collection

Oxford Diffraction Xcalibur with a Sapphire3 detector, removed Mo collimator (Gemini ultra Cu) diffractometer	11730 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	9828 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.020
Detector resolution: 15.9578 pixels mm^-1	θmax = 71.5°, θmin = 3.0°
ω scans	h = −8→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −18→15
Tmin = 0.955, Tmax = 1.000	l = −53→51
18369 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.032	w = 1/[σ^2(Fo^2) + (0.026P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.068	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.17 e Å^−3
11730 reflections	Δρmin = −0.14 e Å^−3
749 parameters	Absolute structure: Flack x determined using 3758 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
7 restraints	Absolute structure parameter: −0.08 (6)
Primary atom site location: structure-invariant direct methods

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
B1	0.2552 (3)	0.20034 (14)	0.12782 (5)	0.0366 (5)
O10	0.1169 (2)	−0.00900 (9)	0.13000 (3)	0.0515 (4)
O11	0.24801 (17)	0.10756 (8)	0.11753 (3)	0.0389 (3)
O12	0.15153 (18)	0.20465 (8)	0.15238 (3)	0.0415 (3)
O20	0.59451 (19)	0.30140 (11)	0.12013 (4)	0.0560 (4)
O21	0.41048 (19)	0.21922 (10)	0.13722 (3)	0.0443 (4)
O22	0.22467 (16)	0.25894 (8)	0.10371 (3)	0.0365 (3)
C11	0.1542 (3)	0.06464 (12)	0.13431 (5)	0.0388 (5)
C12	0.1009 (3)	0.12201 (12)	0.15986 (4)	0.0392 (5)
H12	−0.0097	0.1220	0.1603	0.047*
C13	0.1588 (3)	0.08917 (13)	0.18965 (5)	0.0419 (5)
C14	0.0996 (3)	0.01398 (15)	0.20171 (5)	0.0523 (6)
H14	0.0210	−0.0146	0.1917	0.063*
C15	0.1552 (4)	−0.01906 (18)	0.22831 (6)	0.0641 (8)
H15	0.1165	−0.0711	0.2362	0.077*
C16	0.2659 (4)	0.02316 (19)	0.24329 (5)	0.0657 (8)
H16	0.3028	0.0008	0.2617	0.079*
C17	0.3237 (3)	0.09774 (19)	0.23178 (5)	0.0606 (7)
H17	0.3998	0.1270	0.2424	0.073*
C18	0.2715 (3)	0.13069 (16)	0.20472 (5)	0.0496 (6)
H18	0.3133	0.1816	0.1966	0.060*
C21	0.4709 (3)	0.27343 (14)	0.11806 (5)	0.0413 (5)
C22	0.3600 (2)	0.29318 (12)	0.09341 (5)	0.0365 (4)
H22	0.3502	0.3567	0.0912	0.044*
C23	0.4112 (3)	0.25482 (12)	0.06385 (4)	0.0362 (5)
C24	0.5400 (3)	0.28465 (14)	0.05032 (5)	0.0507 (6)
H24	0.5954	0.3293	0.0595	0.061*
C25	0.5876 (3)	0.24931 (17)	0.02343 (6)	0.0626 (7)
H25	0.6753	0.2702	0.0142	0.075*
C26	0.5094 (4)	0.18443 (17)	0.00999 (5)	0.0600 (7)
H26	0.5422	0.1610	−0.0085	0.072*
C27	0.3833 (3)	0.15347 (15)	0.02340 (5)	0.0531 (6)
H27	0.3299	0.1078	0.0143	0.064*
C28	0.3340 (3)	0.18881 (13)	0.05016 (5)	0.0417 (5)
H28	0.2462	0.1675	0.0592	0.050*
B2	0.2494 (3)	0.69434 (14)	0.12041 (5)	0.0363 (5)
O30	0.37923 (19)	0.48321 (8)	0.12134 (3)	0.0446 (4)
O31	0.25653 (17)	0.60373 (8)	0.13266 (3)	0.0389 (3)
O32	0.34815 (17)	0.69342 (8)	0.09508 (3)	0.0398 (3)
O40	−0.08534 (19)	0.80183 (11)	0.12755 (4)	0.0544 (4)
O41	0.09209 (18)	0.71200 (10)	0.11171 (3)	0.0435 (4)
O42	0.28483 (16)	0.75811 (8)	0.14237 (3)	0.0367 (3)
C31	0.3448 (2)	0.55674 (12)	0.11588 (4)	0.0355 (4)
C32	0.3963 (2)	0.60912 (12)	0.08900 (4)	0.0372 (4)
H32	0.5069	0.6085	0.0884	0.045*
C33	0.3377 (3)	0.57454 (12)	0.05951 (4)	0.0368 (4)
C34	0.4057 (3)	0.50481 (14)	0.04609 (5)	0.0474 (5)
H34	0.4898	0.4796	0.0554	0.057*
C35	0.3532 (3)	0.47149 (15)	0.01950 (5)	0.0550 (7)
H35	0.4008	0.4235	0.0106	0.066*
C36	0.2314 (3)	0.50780 (15)	0.00578 (5)	0.0517 (6)
H36	0.1950	0.4852	−0.0126	0.062*
C37	0.1632 (3)	0.57693 (15)	0.01896 (5)	0.0512 (6)
H37	0.0796	0.6023	0.0096	0.061*
C38	0.2150 (3)	0.61009 (14)	0.04579 (5)	0.0443 (5)
H38	0.1661	0.6575	0.0548	0.053*
C41	0.0373 (3)	0.77193 (14)	0.12975 (5)	0.0408 (5)
C42	0.1524 (2)	0.79524 (12)	0.15301 (5)	0.0361 (4)
H42	0.1637	0.8590	0.1538	0.043*
C43	0.1076 (3)	0.76167 (12)	0.18401 (5)	0.0372 (5)
C44	−0.0252 (3)	0.78695 (15)	0.19695 (5)	0.0497 (6)
H44	−0.0887	0.8254	0.1866	0.060*
C45	−0.0653 (3)	0.75609 (18)	0.22502 (6)	0.0592 (7)
H45	−0.1565	0.7733	0.2337	0.071*
C46	0.0260 (3)	0.70074 (17)	0.24039 (5)	0.0579 (7)
H46	−0.0015	0.6801	0.2597	0.070*
C47	0.1565 (4)	0.67577 (17)	0.22759 (5)	0.0608 (7)
H47	0.2198	0.6375	0.2381	0.073*
C48	0.1979 (3)	0.70574 (15)	0.19938 (5)	0.0500 (6)
H48	0.2886	0.6875	0.1907	0.060*
N1	0.9177 (2)	0.43086 (10)	0.15627 (3)	0.0340 (4)
C51	0.9134 (2)	0.39874 (12)	0.12401 (4)	0.0336 (4)
H51A	0.9370	0.3367	0.1240	0.040*
H51B	0.8112	0.4052	0.1163	0.040*
C52	1.0185 (2)	0.44392 (13)	0.10252 (4)	0.0355 (4)
H52A	1.1219	0.4282	0.1073	0.043*
H52B	1.0081	0.5068	0.1047	0.043*
C53	0.9824 (3)	0.41744 (14)	0.07031 (5)	0.0450 (5)
H53A	1.0680	0.4309	0.0573	0.054*
H53B	0.9664	0.3547	0.0697	0.054*
C54	0.8463 (3)	0.46220 (18)	0.05808 (6)	0.0638 (7)
H54A	0.8256	0.4412	0.0378	0.096*
H54B	0.8639	0.5242	0.0574	0.096*
H54C	0.7615	0.4502	0.0711	0.096*
C55	0.8023 (2)	0.38180 (12)	0.17420 (5)	0.0381 (5)
H55A	0.7044	0.3919	0.1649	0.046*
H55B	0.7989	0.4062	0.1947	0.046*
C56	0.8255 (2)	0.28541 (13)	0.17681 (4)	0.0383 (5)
H56A	0.9206	0.2736	0.1870	0.046*
H56B	0.8295	0.2595	0.1565	0.046*
C57	0.6989 (3)	0.24588 (14)	0.19462 (5)	0.0456 (5)
H57A	0.6035	0.2653	0.1861	0.055*
H57B	0.7040	0.2660	0.2157	0.055*
C58	0.7046 (3)	0.14814 (14)	0.19411 (6)	0.0530 (6)
H58A	0.7998	0.1287	0.2022	0.080*
H58B	0.6935	0.1278	0.1734	0.080*
H58C	0.6241	0.1251	0.2064	0.080*
C61	0.8798 (3)	0.52628 (12)	0.15786 (5)	0.0397 (5)
H61A	0.8668	0.5422	0.1792	0.048*
H61B	0.9650	0.5593	0.1500	0.048*
C62	0.7415 (3)	0.55348 (14)	0.14064 (5)	0.0474 (5)
H62A	0.6626	0.5103	0.1437	0.057*
H62B	0.7642	0.5557	0.1189	0.057*
C63	0.6855 (3)	0.64153 (13)	0.15097 (6)	0.0517 (6)
H63A	0.7697	0.6822	0.1511	0.062*
H63B	0.6122	0.6628	0.1362	0.062*
C64	0.6163 (4)	0.6411 (2)	0.18124 (7)	0.0772 (9)
H64A	0.5369	0.5983	0.1818	0.116*
H64B	0.5751	0.6980	0.1855	0.116*
H64C	0.6911	0.6269	0.1964	0.116*
C65	1.0728 (2)	0.41665 (14)	0.16839 (4)	0.0388 (5)
H65A	1.1423	0.4532	0.1569	0.047*
H65B	1.1010	0.3562	0.1648	0.047*
C66	1.0914 (3)	0.43598 (18)	0.20178 (5)	0.0529 (6)
H66C	1.0083	0.4109	0.2133	0.063*	0.466 (7)
H66D	1.0918	0.4987	0.2051	0.063*	0.466 (7)
H66A	1.0602	0.3855	0.2137	0.063*	0.534 (7)
H66B	1.0272	0.4848	0.2074	0.063*	0.534 (7)
C67B	1.2386 (6)	0.3969 (5)	0.21230 (12)	0.058 (2)	0.466 (7)
H67A	1.2427	0.3974	0.2345	0.069*	0.466 (7)
H67B	1.2449	0.3365	0.2055	0.069*	0.466 (7)
C68B	1.3687 (7)	0.4470 (5)	0.19981 (14)	0.064 (2)	0.466 (7)
H68A	1.4614	0.4205	0.2065	0.096*	0.466 (7)
H68B	1.3643	0.5063	0.2071	0.096*	0.466 (7)
H68C	1.3646	0.4466	0.1778	0.096*	0.466 (7)
C67A	1.2556 (5)	0.4582 (4)	0.20926 (11)	0.0520 (16)	0.534 (7)
H67C	1.2873	0.5079	0.1970	0.062*	0.534 (7)
H67D	1.2634	0.4746	0.2307	0.062*	0.534 (7)
C68A	1.3563 (8)	0.3837 (4)	0.20318 (14)	0.071 (2)	0.534 (7)
H68D	1.4579	0.3990	0.2087	0.107*	0.534 (7)
H68E	1.3525	0.3691	0.1818	0.107*	0.534 (7)
H68F	1.3243	0.3342	0.2151	0.107*	0.534 (7)
N2	0.56404 (18)	0.93029 (10)	0.09488 (3)	0.0302 (3)
C71	0.4458 (2)	0.95776 (12)	0.07259 (4)	0.0311 (4)
H71A	0.4148	1.0169	0.0776	0.037*
H71B	0.4905	0.9592	0.0523	0.037*
C72	0.3090 (2)	0.90149 (12)	0.07146 (4)	0.0345 (4)
H72A	0.2612	0.9003	0.0915	0.041*
H72B	0.3374	0.8421	0.0661	0.041*
C73	0.2011 (2)	0.93622 (13)	0.04834 (5)	0.0407 (5)
H73A	0.2476	0.9341	0.0282	0.049*
H73B	0.1787	0.9969	0.0530	0.049*
C74	0.0576 (3)	0.88500 (16)	0.04783 (6)	0.0508 (6)
H74A	0.0094	0.8888	0.0675	0.076*
H74B	0.0794	0.8248	0.0433	0.076*
H74C	−0.0084	0.9084	0.0324	0.076*
C75	0.6133 (2)	0.83792 (11)	0.08935 (4)	0.0328 (4)
H75A	0.7007	0.8261	0.1021	0.039*
H75B	0.5331	0.7990	0.0959	0.039*
C76	0.6524 (2)	0.81651 (12)	0.05704 (4)	0.0367 (4)
H76A	0.7174	0.8618	0.0488	0.044*
H76B	0.5610	0.8147	0.0448	0.044*
C77	0.7310 (3)	0.73026 (12)	0.05519 (5)	0.0450 (5)
H77A	0.8254	0.7337	0.0664	0.054*
H77B	0.6688	0.6860	0.0649	0.054*
C78	0.7625 (4)	0.70362 (17)	0.02329 (6)	0.0679 (8)
H78A	0.6691	0.6981	0.0123	0.102*
H78B	0.8142	0.6484	0.0233	0.102*
H78C	0.8246	0.7470	0.0136	0.102*
C81	0.6985 (2)	0.98844 (11)	0.09174 (4)	0.0324 (4)
H81A	0.7734	0.9705	0.1067	0.039*
H81B	0.7419	0.9795	0.0716	0.039*
C82	0.6690 (3)	1.08382 (12)	0.09585 (5)	0.0412 (5)
H82A	0.6172	1.0933	0.1152	0.049*
H82B	0.6039	1.1045	0.0795	0.049*
C83	0.8133 (3)	1.13459 (14)	0.09557 (6)	0.0510 (6)
H83A	0.7910	1.1952	0.1004	0.061*
H83B	0.8785	1.1122	0.1116	0.061*
C84	0.8960 (3)	1.13142 (16)	0.06618 (7)	0.0676 (8)
H84A	0.8295	1.1481	0.0498	0.101*
H84B	0.9323	1.0730	0.0627	0.101*
H84C	0.9800	1.1711	0.0669	0.101*
C85	0.4972 (2)	0.93626 (13)	0.12619 (4)	0.0344 (4)
H85A	0.4550	0.9944	0.1287	0.041*
H85B	0.4141	0.8950	0.1274	0.041*
C86	0.6004 (3)	0.91928 (14)	0.15232 (4)	0.0396 (5)
H86A	0.6798	0.9630	0.1529	0.048*
H86B	0.6467	0.8621	0.1502	0.048*
C87	0.5094 (3)	0.92308 (16)	0.18112 (5)	0.0471 (6)
H87A	0.4621	0.9802	0.1827	0.057*
H87B	0.4297	0.8796	0.1801	0.057*
C88	0.6021 (3)	0.90714 (18)	0.20909 (5)	0.0594 (7)
H88A	0.6414	0.8486	0.2086	0.089*
H88B	0.5404	0.9145	0.2270	0.089*
H88C	0.6844	0.9481	0.2097	0.089*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
B1	0.0356 (13)	0.0363 (11)	0.0377 (11)	0.0053 (10)	0.0044 (10)	−0.0023 (9)
O10	0.0692 (12)	0.0356 (8)	0.0496 (9)	0.0000 (8)	0.0059 (9)	0.0005 (6)
O11	0.0435 (9)	0.0352 (7)	0.0381 (7)	0.0069 (7)	0.0088 (7)	0.0007 (6)
O12	0.0460 (9)	0.0350 (7)	0.0435 (8)	0.0051 (7)	0.0130 (7)	−0.0017 (6)
O20	0.0361 (10)	0.0669 (10)	0.0652 (10)	−0.0095 (8)	−0.0044 (8)	−0.0132 (8)
O21	0.0375 (9)	0.0566 (9)	0.0387 (8)	0.0032 (7)	−0.0013 (7)	0.0008 (7)
O22	0.0295 (8)	0.0362 (7)	0.0438 (7)	0.0023 (6)	0.0033 (6)	0.0033 (6)
C11	0.0407 (12)	0.0380 (10)	0.0376 (10)	0.0079 (10)	0.0016 (9)	0.0045 (8)
C12	0.0365 (12)	0.0395 (10)	0.0416 (11)	0.0041 (9)	0.0077 (10)	0.0018 (8)
C13	0.0403 (12)	0.0472 (12)	0.0383 (11)	0.0065 (10)	0.0119 (10)	−0.0007 (9)
C14	0.0585 (16)	0.0563 (13)	0.0422 (12)	−0.0006 (13)	0.0121 (12)	0.0036 (10)
C15	0.081 (2)	0.0656 (16)	0.0454 (14)	0.0047 (16)	0.0165 (15)	0.0114 (12)
C16	0.072 (2)	0.089 (2)	0.0363 (12)	0.0156 (17)	0.0078 (13)	0.0106 (12)
C17	0.0532 (16)	0.0883 (19)	0.0404 (12)	0.0040 (15)	0.0023 (12)	−0.0048 (13)
C18	0.0463 (14)	0.0605 (14)	0.0420 (12)	0.0023 (12)	0.0108 (11)	−0.0010 (10)
C21	0.0364 (13)	0.0430 (11)	0.0445 (12)	−0.0007 (10)	0.0027 (10)	−0.0103 (9)
C22	0.0331 (11)	0.0289 (9)	0.0475 (11)	0.0006 (8)	0.0040 (9)	−0.0002 (8)
C23	0.0374 (12)	0.0298 (9)	0.0414 (11)	0.0058 (9)	0.0018 (9)	0.0078 (8)
C24	0.0495 (15)	0.0433 (12)	0.0592 (14)	−0.0013 (11)	0.0141 (12)	0.0052 (11)
C25	0.0610 (18)	0.0666 (16)	0.0601 (15)	0.0104 (15)	0.0250 (14)	0.0155 (13)
C26	0.078 (2)	0.0632 (16)	0.0389 (12)	0.0238 (15)	0.0093 (13)	0.0024 (11)
C27	0.0674 (19)	0.0548 (13)	0.0371 (12)	0.0070 (13)	−0.0052 (12)	−0.0023 (10)
C28	0.0443 (13)	0.0435 (11)	0.0375 (11)	0.0031 (10)	−0.0044 (10)	0.0036 (9)
B2	0.0363 (13)	0.0325 (10)	0.0401 (12)	−0.0067 (10)	0.0015 (11)	0.0032 (9)
O30	0.0518 (10)	0.0336 (7)	0.0483 (8)	−0.0012 (7)	−0.0058 (8)	0.0026 (6)
O31	0.0439 (9)	0.0326 (7)	0.0402 (7)	−0.0057 (7)	0.0049 (7)	0.0017 (6)
O32	0.0457 (9)	0.0304 (6)	0.0432 (8)	−0.0048 (6)	0.0079 (7)	0.0019 (6)
O40	0.0348 (10)	0.0712 (11)	0.0572 (10)	0.0085 (8)	−0.0048 (8)	0.0098 (8)
O41	0.0384 (9)	0.0509 (8)	0.0413 (8)	−0.0026 (7)	−0.0057 (7)	−0.0016 (6)
O42	0.0303 (8)	0.0340 (7)	0.0457 (8)	−0.0025 (6)	−0.0009 (6)	−0.0017 (5)
C31	0.0331 (11)	0.0340 (10)	0.0393 (10)	−0.0051 (9)	−0.0050 (9)	−0.0012 (8)
C32	0.0332 (11)	0.0322 (9)	0.0463 (11)	−0.0037 (9)	0.0016 (9)	0.0011 (8)
C33	0.0376 (11)	0.0356 (10)	0.0373 (10)	−0.0049 (9)	0.0055 (9)	0.0044 (8)
C34	0.0494 (14)	0.0489 (12)	0.0438 (12)	0.0089 (11)	0.0002 (11)	−0.0009 (10)
C35	0.072 (2)	0.0504 (13)	0.0431 (12)	0.0104 (13)	0.0040 (12)	−0.0051 (10)
C36	0.0683 (18)	0.0549 (13)	0.0319 (11)	−0.0070 (13)	0.0007 (11)	0.0025 (9)
C37	0.0533 (15)	0.0620 (14)	0.0382 (11)	0.0054 (12)	−0.0028 (11)	0.0108 (10)
C38	0.0477 (14)	0.0437 (11)	0.0417 (11)	0.0042 (11)	0.0010 (10)	0.0048 (9)
C41	0.0337 (12)	0.0461 (12)	0.0426 (11)	−0.0011 (9)	0.0006 (10)	0.0099 (9)
C42	0.0305 (11)	0.0308 (9)	0.0469 (11)	−0.0008 (9)	0.0014 (9)	0.0019 (8)
C43	0.0358 (12)	0.0336 (9)	0.0422 (11)	−0.0043 (9)	−0.0025 (9)	−0.0043 (8)
C44	0.0424 (14)	0.0563 (14)	0.0504 (13)	0.0072 (11)	0.0013 (11)	0.0019 (11)
C45	0.0476 (16)	0.0797 (18)	0.0501 (13)	0.0046 (14)	0.0097 (12)	−0.0002 (12)
C46	0.0650 (18)	0.0686 (16)	0.0402 (12)	−0.0054 (14)	0.0026 (12)	0.0032 (11)
C47	0.072 (2)	0.0667 (16)	0.0441 (13)	0.0156 (15)	−0.0024 (13)	0.0073 (11)
C48	0.0488 (14)	0.0564 (13)	0.0447 (12)	0.0141 (12)	0.0018 (11)	0.0030 (10)
N1	0.0334 (9)	0.0362 (8)	0.0322 (8)	−0.0017 (7)	0.0024 (7)	−0.0028 (6)
C51	0.0331 (11)	0.0366 (9)	0.0310 (9)	−0.0020 (9)	−0.0004 (8)	−0.0026 (8)
C52	0.0329 (11)	0.0391 (11)	0.0346 (10)	−0.0023 (9)	0.0026 (9)	−0.0007 (8)
C53	0.0513 (14)	0.0489 (12)	0.0349 (11)	−0.0053 (11)	0.0050 (10)	−0.0004 (9)
C54	0.0657 (19)	0.0837 (18)	0.0421 (13)	−0.0031 (15)	−0.0124 (13)	0.0073 (12)
C55	0.0338 (11)	0.0437 (11)	0.0368 (10)	−0.0006 (9)	0.0074 (9)	−0.0030 (8)
C56	0.0343 (11)	0.0448 (11)	0.0358 (10)	−0.0007 (9)	0.0046 (9)	0.0012 (8)
C57	0.0411 (13)	0.0524 (12)	0.0432 (12)	−0.0028 (11)	0.0097 (10)	0.0055 (10)
C58	0.0518 (15)	0.0537 (13)	0.0536 (14)	−0.0116 (12)	0.0104 (12)	0.0053 (10)
C61	0.0409 (13)	0.0350 (10)	0.0431 (11)	−0.0022 (9)	0.0004 (10)	−0.0079 (8)
C62	0.0469 (14)	0.0435 (12)	0.0518 (13)	0.0062 (11)	−0.0040 (11)	−0.0041 (9)
C63	0.0479 (15)	0.0410 (12)	0.0662 (16)	0.0021 (11)	−0.0046 (13)	−0.0011 (10)
C64	0.065 (2)	0.084 (2)	0.083 (2)	0.0259 (17)	0.0042 (17)	−0.0171 (16)
C65	0.0321 (11)	0.0499 (12)	0.0345 (10)	−0.0003 (9)	0.0000 (9)	0.0004 (8)
C66	0.0429 (14)	0.0794 (17)	0.0363 (11)	0.0009 (13)	−0.0029 (11)	−0.0047 (11)
C67B	0.068 (5)	0.062 (4)	0.043 (3)	−0.010 (4)	−0.021 (3)	0.011 (3)
C68B	0.048 (4)	0.091 (6)	0.054 (3)	0.010 (4)	−0.006 (3)	0.001 (3)
C67A	0.052 (4)	0.059 (4)	0.045 (3)	0.006 (3)	−0.015 (2)	−0.008 (2)
C68A	0.062 (4)	0.079 (4)	0.073 (4)	0.029 (4)	−0.021 (3)	−0.026 (3)
N2	0.0253 (8)	0.0332 (8)	0.0321 (8)	0.0023 (7)	−0.0003 (7)	0.0022 (6)
C71	0.0275 (10)	0.0327 (9)	0.0332 (9)	0.0033 (8)	−0.0019 (8)	0.0033 (7)
C72	0.0298 (11)	0.0365 (9)	0.0372 (10)	0.0007 (9)	−0.0020 (8)	0.0034 (8)
C73	0.0343 (12)	0.0429 (11)	0.0448 (11)	0.0007 (10)	−0.0062 (9)	0.0027 (9)
C74	0.0345 (13)	0.0587 (14)	0.0592 (14)	−0.0022 (11)	−0.0111 (11)	0.0046 (11)
C75	0.0286 (10)	0.0302 (9)	0.0397 (10)	0.0031 (8)	0.0006 (9)	0.0035 (8)
C76	0.0371 (11)	0.0347 (10)	0.0382 (10)	0.0029 (9)	−0.0033 (9)	−0.0008 (8)
C77	0.0486 (14)	0.0353 (10)	0.0512 (12)	0.0051 (10)	0.0074 (11)	0.0002 (9)
C78	0.087 (2)	0.0549 (14)	0.0618 (15)	0.0222 (15)	−0.0028 (16)	−0.0186 (12)
C81	0.0255 (10)	0.0354 (9)	0.0364 (10)	0.0013 (8)	0.0000 (8)	0.0004 (8)
C82	0.0358 (12)	0.0378 (10)	0.0499 (12)	0.0004 (9)	0.0026 (10)	−0.0063 (9)
C83	0.0425 (14)	0.0412 (11)	0.0692 (16)	−0.0043 (10)	−0.0109 (12)	−0.0090 (10)
C84	0.0466 (16)	0.0489 (14)	0.107 (2)	−0.0081 (12)	0.0230 (16)	−0.0017 (14)
C85	0.0284 (10)	0.0401 (10)	0.0346 (10)	0.0044 (9)	0.0028 (8)	0.0009 (8)
C86	0.0372 (12)	0.0473 (11)	0.0343 (10)	0.0057 (10)	−0.0017 (9)	−0.0021 (8)
C87	0.0458 (14)	0.0627 (14)	0.0328 (11)	0.0097 (12)	0.0003 (10)	−0.0025 (10)
C88	0.0612 (17)	0.0822 (18)	0.0347 (11)	0.0152 (15)	−0.0022 (11)	−0.0001 (11)

Geometric parameters (Å, º)

B1—O11	1.519 (3)	C56—H56A	0.9900
B1—O12	1.442 (3)	C56—H56B	0.9900
B1—O21	1.494 (3)	C56—C57	1.523 (3)
B1—O22	1.437 (3)	C57—H57A	0.9900
O10—C11	1.212 (2)	C57—H57B	0.9900
O11—C11	1.313 (3)	C57—C58	1.525 (3)
O12—C12	1.407 (2)	C58—H58A	0.9800
O20—C21	1.203 (3)	C58—H58B	0.9800
O21—C21	1.319 (3)	C58—H58C	0.9800
O22—C22	1.411 (2)	C61—H61A	0.9900
C11—C12	1.526 (3)	C61—H61B	0.9900
C12—H12	1.0000	C61—C62	1.526 (3)
C12—C13	1.515 (3)	C62—H62A	0.9900
C13—C14	1.396 (3)	C62—H62B	0.9900
C13—C18	1.381 (3)	C62—C63	1.534 (3)
C14—H14	0.9500	C63—H63A	0.9900
C14—C15	1.386 (4)	C63—H63B	0.9900
C15—H15	0.9500	C63—C64	1.486 (4)
C15—C16	1.371 (4)	C64—H64A	0.9800
C16—H16	0.9500	C64—H64B	0.9800
C16—C17	1.374 (4)	C64—H64C	0.9800
C17—H17	0.9500	C65—H65A	0.9900
C17—C18	1.393 (3)	C65—H65B	0.9900
C18—H18	0.9500	C65—C66	1.527 (3)
C21—C22	1.518 (3)	C66—H66C	0.9900
C22—H22	1.0000	C66—H66D	0.9900
C22—C23	1.518 (3)	C66—H66A	0.9900
C23—C24	1.391 (3)	C66—H66B	0.9900
C23—C28	1.385 (3)	C66—C67B	1.536 (6)
C24—H24	0.9500	C66—C67A	1.560 (5)
C24—C25	1.387 (3)	C67B—H67A	0.9900
C25—H25	0.9500	C67B—H67B	0.9900
C25—C26	1.372 (4)	C67B—C68B	1.517 (7)
C26—H26	0.9500	C68B—H68A	0.9800
C26—C27	1.374 (4)	C68B—H68B	0.9800
C27—H27	0.9500	C68B—H68C	0.9800
C27—C28	1.387 (3)	C67A—H67C	0.9900
C28—H28	0.9500	C67A—H67D	0.9900
B2—O31	1.516 (3)	C67A—C68A	1.501 (7)
B2—O32	1.438 (3)	C68A—H68D	0.9800
B2—O41	1.499 (3)	C68A—H68E	0.9800
B2—O42	1.431 (3)	C68A—H68F	0.9800
O30—C31	1.213 (2)	N2—C71	1.520 (2)
O31—C31	1.316 (3)	N2—C75	1.528 (2)
O32—C32	1.411 (2)	N2—C81	1.523 (2)
O40—C41	1.206 (3)	N2—C85	1.523 (2)
O41—C41	1.328 (3)	C71—H71A	0.9900
O42—C42	1.411 (2)	C71—H71B	0.9900
C31—C32	1.522 (3)	C71—C72	1.517 (3)
C32—H32	1.0000	C72—H72A	0.9900
C32—C33	1.515 (3)	C72—H72B	0.9900
C33—C34	1.384 (3)	C72—C73	1.518 (3)
C33—C38	1.382 (3)	C73—H73A	0.9900
C34—H34	0.9500	C73—H73B	0.9900
C34—C35	1.377 (3)	C73—C74	1.524 (3)
C35—H35	0.9500	C74—H74A	0.9800
C35—C36	1.381 (4)	C74—H74B	0.9800
C36—H36	0.9500	C74—H74C	0.9800
C36—C37	1.373 (3)	C75—H75A	0.9900
C37—H37	0.9500	C75—H75B	0.9900
C37—C38	1.384 (3)	C75—C76	1.519 (3)
C38—H38	0.9500	C76—H76A	0.9900
C41—C42	1.513 (3)	C76—H76B	0.9900
C42—H42	1.0000	C76—C77	1.523 (3)
C42—C43	1.531 (3)	C77—H77A	0.9900
C43—C44	1.389 (3)	C77—H77B	0.9900
C43—C48	1.376 (3)	C77—C78	1.507 (3)
C44—H44	0.9500	C78—H78A	0.9800
C44—C45	1.387 (3)	C78—H78B	0.9800
C45—H45	0.9500	C78—H78C	0.9800
C45—C46	1.376 (4)	C81—H81A	0.9900
C46—H46	0.9500	C81—H81B	0.9900
C46—C47	1.367 (4)	C81—C82	1.522 (2)
C47—H47	0.9500	C82—H82A	0.9900
C47—C48	1.392 (3)	C82—H82B	0.9900
C48—H48	0.9500	C82—C83	1.525 (3)
N1—C51	1.522 (2)	C83—H83A	0.9900
N1—C55	1.520 (3)	C83—H83B	0.9900
N1—C61	1.529 (2)	C83—C84	1.509 (4)
N1—C65	1.519 (3)	C84—H84A	0.9800
C51—H51A	0.9900	C84—H84B	0.9800
C51—H51B	0.9900	C84—H84C	0.9800
C51—C52	1.521 (3)	C85—H85A	0.9900
C52—H52A	0.9900	C85—H85B	0.9900
C52—H52B	0.9900	C85—C86	1.515 (3)
C52—C53	1.528 (3)	C86—H86A	0.9900
C53—H53A	0.9900	C86—H86B	0.9900
C53—H53B	0.9900	C86—C87	1.525 (3)
C53—C54	1.515 (4)	C87—H87A	0.9900
C54—H54A	0.9800	C87—H87B	0.9900
C54—H54B	0.9800	C87—C88	1.522 (3)
C54—H54C	0.9800	C88—H88A	0.9800
C55—H55A	0.9900	C88—H88B	0.9800
C55—H55B	0.9900	C88—H88C	0.9800
C55—C56	1.522 (3)
O12—B1—O11	104.22 (17)	C58—C57—H57B	109.3
O12—B1—O21	112.87 (17)	C57—C58—H58A	109.5
O21—B1—O11	108.22 (18)	C57—C58—H58B	109.5
O22—B1—O11	111.84 (16)	C57—C58—H58C	109.5
O22—B1—O12	114.35 (18)	H58A—C58—H58B	109.5
O22—B1—O21	105.34 (18)	H58A—C58—H58C	109.5
C11—O11—B1	109.95 (16)	H58B—C58—H58C	109.5
C12—O12—B1	110.37 (15)	N1—C61—H61A	108.4
C21—O21—B1	109.49 (17)	N1—C61—H61B	108.4
C22—O22—B1	108.51 (17)	H61A—C61—H61B	107.5
O10—C11—O11	124.89 (19)	C62—C61—N1	115.53 (17)
O10—C11—C12	125.9 (2)	C62—C61—H61A	108.4
O11—C11—C12	109.23 (17)	C62—C61—H61B	108.4
O12—C12—C11	104.93 (16)	C61—C62—H62A	109.3
O12—C12—H12	109.2	C61—C62—H62B	109.3
O12—C12—C13	113.88 (18)	C61—C62—C63	111.59 (19)
C11—C12—H12	109.2	H62A—C62—H62B	108.0
C13—C12—C11	110.25 (17)	C63—C62—H62A	109.3
C13—C12—H12	109.2	C63—C62—H62B	109.3
C14—C13—C12	119.2 (2)	C62—C63—H63A	108.7
C18—C13—C12	121.4 (2)	C62—C63—H63B	108.7
C18—C13—C14	119.3 (2)	H63A—C63—H63B	107.6
C13—C14—H14	119.9	C64—C63—C62	114.0 (2)
C15—C14—C13	120.1 (3)	C64—C63—H63A	108.7
C15—C14—H14	119.9	C64—C63—H63B	108.7
C14—C15—H15	119.9	C63—C64—H64A	109.5
C16—C15—C14	120.1 (3)	C63—C64—H64B	109.5
C16—C15—H15	119.9	C63—C64—H64C	109.5
C15—C16—H16	119.9	H64A—C64—H64B	109.5
C15—C16—C17	120.2 (3)	H64A—C64—H64C	109.5
C17—C16—H16	119.9	H64B—C64—H64C	109.5
C16—C17—H17	119.8	N1—C65—H65A	108.6
C16—C17—C18	120.4 (3)	N1—C65—H65B	108.6
C18—C17—H17	119.8	N1—C65—C66	114.75 (18)
C13—C18—C17	119.8 (2)	H65A—C65—H65B	107.6
C13—C18—H18	120.1	C66—C65—H65A	108.6
C17—C18—H18	120.1	C66—C65—H65B	108.6
O20—C21—O21	124.5 (2)	C65—C66—H66C	110.0
O20—C21—C22	126.5 (2)	C65—C66—H66D	110.0
O21—C21—C22	108.94 (19)	C65—C66—H66A	109.5
O22—C22—C21	105.07 (16)	C65—C66—H66B	109.5
O22—C22—H22	109.3	C65—C66—C67B	108.3 (3)
O22—C22—C23	113.40 (17)	C65—C66—C67A	110.9 (3)
C21—C22—H22	109.3	H66C—C66—H66D	108.4
C21—C22—C23	110.24 (17)	H66A—C66—H66B	108.1
C23—C22—H22	109.3	C67B—C66—H66C	110.0
C24—C23—C22	119.9 (2)	C67B—C66—H66D	110.0
C28—C23—C22	121.4 (2)	C67A—C66—H66A	109.5
C28—C23—C24	118.6 (2)	C67A—C66—H66B	109.5
C23—C24—H24	120.0	C66—C67B—H67A	109.5
C25—C24—C23	120.1 (2)	C66—C67B—H67B	109.5
C25—C24—H24	120.0	H67A—C67B—H67B	108.1
C24—C25—H25	119.7	C68B—C67B—C66	110.8 (5)
C26—C25—C24	120.7 (3)	C68B—C67B—H67A	109.5
C26—C25—H25	119.7	C68B—C67B—H67B	109.5
C25—C26—H26	120.1	C67B—C68B—H68A	109.5
C25—C26—C27	119.8 (2)	C67B—C68B—H68B	109.5
C27—C26—H26	120.1	C67B—C68B—H68C	109.5
C26—C27—H27	120.0	H68A—C68B—H68B	109.5
C26—C27—C28	120.0 (2)	H68A—C68B—H68C	109.5
C28—C27—H27	120.0	H68B—C68B—H68C	109.5
C23—C28—C27	120.8 (2)	C66—C67A—H67C	109.3
C23—C28—H28	119.6	C66—C67A—H67D	109.3
C27—C28—H28	119.6	H67C—C67A—H67D	108.0
O32—B2—O31	104.29 (17)	C68A—C67A—C66	111.5 (5)
O32—B2—O41	112.81 (17)	C68A—C67A—H67C	109.3
O41—B2—O31	107.73 (17)	C68A—C67A—H67D	109.3
O42—B2—O31	113.08 (17)	C67A—C68A—H68D	109.5
O42—B2—O32	113.84 (18)	C67A—C68A—H68E	109.5
O42—B2—O41	105.13 (17)	C67A—C68A—H68F	109.5
C31—O31—B2	109.88 (16)	H68D—C68A—H68E	109.5
C32—O32—B2	110.55 (15)	H68D—C68A—H68F	109.5
C41—O41—B2	109.08 (16)	H68E—C68A—H68F	109.5
C42—O42—B2	108.96 (17)	C71—N2—C75	111.43 (14)
O30—C31—O31	124.62 (19)	C71—N2—C81	109.47 (14)
O30—C31—C32	125.90 (19)	C71—N2—C85	107.56 (15)
O31—C31—C32	109.47 (16)	C81—N2—C75	108.30 (15)
O32—C32—C31	104.76 (16)	C85—N2—C75	108.73 (14)
O32—C32—H32	108.8	C85—N2—C81	111.37 (15)
O32—C32—C33	112.96 (17)	N2—C71—H71A	108.4
C31—C32—H32	108.8	N2—C71—H71B	108.4
C33—C32—C31	112.57 (16)	H71A—C71—H71B	107.4
C33—C32—H32	108.8	C72—C71—N2	115.58 (15)
C34—C33—C32	119.9 (2)	C72—C71—H71A	108.4
C38—C33—C32	121.39 (19)	C72—C71—H71B	108.4
C38—C33—C34	118.7 (2)	C71—C72—H72A	109.7
C33—C34—H34	119.5	C71—C72—H72B	109.7
C35—C34—C33	121.0 (2)	C71—C72—C73	109.85 (16)
C35—C34—H34	119.5	H72A—C72—H72B	108.2
C34—C35—H35	120.0	C73—C72—H72A	109.7
C34—C35—C36	120.0 (2)	C73—C72—H72B	109.7
C36—C35—H35	120.0	C72—C73—H73A	109.3
C35—C36—H36	120.3	C72—C73—H73B	109.3
C37—C36—C35	119.3 (2)	C72—C73—C74	111.69 (17)
C37—C36—H36	120.3	H73A—C73—H73B	107.9
C36—C37—H37	119.6	C74—C73—H73A	109.3
C36—C37—C38	120.7 (2)	C74—C73—H73B	109.3
C38—C37—H37	119.6	C73—C74—H74A	109.5
C33—C38—C37	120.2 (2)	C73—C74—H74B	109.5
C33—C38—H38	119.9	C73—C74—H74C	109.5
C37—C38—H38	119.9	H74A—C74—H74B	109.5
O40—C41—O41	124.4 (2)	H74A—C74—H74C	109.5
O40—C41—C42	126.5 (2)	H74B—C74—H74C	109.5
O41—C41—C42	109.07 (18)	N2—C75—H75A	108.4
O42—C42—C41	104.76 (16)	N2—C75—H75B	108.4
O42—C42—H42	109.5	H75A—C75—H75B	107.5
O42—C42—C43	112.74 (17)	C76—C75—N2	115.33 (15)
C41—C42—H42	109.5	C76—C75—H75A	108.4
C41—C42—C43	110.71 (17)	C76—C75—H75B	108.4
C43—C42—H42	109.5	C75—C76—H76A	109.5
C44—C43—C42	120.4 (2)	C75—C76—H76B	109.5
C48—C43—C42	120.6 (2)	C75—C76—C77	110.71 (16)
C48—C43—C44	119.1 (2)	H76A—C76—H76B	108.1
C43—C44—H44	120.0	C77—C76—H76A	109.5
C45—C44—C43	120.1 (2)	C77—C76—H76B	109.5
C45—C44—H44	120.0	C76—C77—H77A	109.1
C44—C45—H45	119.7	C76—C77—H77B	109.1
C46—C45—C44	120.6 (3)	H77A—C77—H77B	107.8
C46—C45—H45	119.7	C78—C77—C76	112.47 (19)
C45—C46—H46	120.4	C78—C77—H77A	109.1
C47—C46—C45	119.3 (2)	C78—C77—H77B	109.1
C47—C46—H46	120.4	C77—C78—H78A	109.5
C46—C47—H47	119.6	C77—C78—H78B	109.5
C46—C47—C48	120.8 (2)	C77—C78—H78C	109.5
C48—C47—H47	119.6	H78A—C78—H78B	109.5
C43—C48—C47	120.2 (2)	H78A—C78—H78C	109.5
C43—C48—H48	119.9	H78B—C78—H78C	109.5
C47—C48—H48	119.9	N2—C81—H81A	108.4
C51—N1—C61	110.99 (15)	N2—C81—H81B	108.4
C55—N1—C51	108.22 (15)	H81A—C81—H81B	107.5
C55—N1—C61	108.16 (16)	C82—C81—N2	115.52 (16)
C65—N1—C51	108.12 (15)	C82—C81—H81A	108.4
C65—N1—C55	111.93 (15)	C82—C81—H81B	108.4
C65—N1—C61	109.43 (16)	C81—C82—H82A	109.5
N1—C51—H51A	108.5	C81—C82—H82B	109.5
N1—C51—H51B	108.5	C81—C82—C83	110.87 (18)
H51A—C51—H51B	107.5	H82A—C82—H82B	108.1
C52—C51—N1	115.18 (16)	C83—C82—H82A	109.5
C52—C51—H51A	108.5	C83—C82—H82B	109.5
C52—C51—H51B	108.5	C82—C83—H83A	108.7
C51—C52—H52A	109.8	C82—C83—H83B	108.7
C51—C52—H52B	109.8	H83A—C83—H83B	107.6
C51—C52—C53	109.40 (17)	C84—C83—C82	114.4 (2)
H52A—C52—H52B	108.2	C84—C83—H83A	108.7
C53—C52—H52A	109.8	C84—C83—H83B	108.7
C53—C52—H52B	109.8	C83—C84—H84A	109.5
C52—C53—H53A	109.0	C83—C84—H84B	109.5
C52—C53—H53B	109.0	C83—C84—H84C	109.5
H53A—C53—H53B	107.8	H84A—C84—H84B	109.5
C54—C53—C52	112.7 (2)	H84A—C84—H84C	109.5
C54—C53—H53A	109.0	H84B—C84—H84C	109.5
C54—C53—H53B	109.0	N2—C85—H85A	108.1
C53—C54—H54A	109.5	N2—C85—H85B	108.1
C53—C54—H54B	109.5	H85A—C85—H85B	107.3
C53—C54—H54C	109.5	C86—C85—N2	116.64 (16)
H54A—C54—H54B	109.5	C86—C85—H85A	108.1
H54A—C54—H54C	109.5	C86—C85—H85B	108.1
H54B—C54—H54C	109.5	C85—C86—H86A	110.1
N1—C55—H55A	108.2	C85—C86—H86B	110.1
N1—C55—H55B	108.2	C85—C86—C87	107.89 (18)
N1—C55—C56	116.26 (17)	H86A—C86—H86B	108.4
H55A—C55—H55B	107.4	C87—C86—H86A	110.1
C56—C55—H55A	108.2	C87—C86—H86B	110.1
C56—C55—H55B	108.2	C86—C87—H87A	109.1
C55—C56—H56A	109.7	C86—C87—H87B	109.1
C55—C56—H56B	109.7	H87A—C87—H87B	107.8
C55—C56—C57	109.63 (18)	C88—C87—C86	112.6 (2)
H56A—C56—H56B	108.2	C88—C87—H87A	109.1
C57—C56—H56A	109.7	C88—C87—H87B	109.1
C57—C56—H56B	109.7	C87—C88—H88A	109.5
C56—C57—H57A	109.3	C87—C88—H88B	109.5
C56—C57—H57B	109.3	C87—C88—H88C	109.5
C56—C57—C58	111.81 (19)	H88A—C88—H88B	109.5
H57A—C57—H57B	107.9	H88A—C88—H88C	109.5
C58—C57—H57A	109.3	H88B—C88—H88C	109.5
B1—O11—C11—O10	174.1 (2)	O40—C41—C42—C43	70.8 (3)
B1—O11—C11—C12	−6.1 (2)	O41—B2—O31—C31	118.46 (18)
B1—O12—C12—C11	−11.4 (2)	O41—B2—O32—C32	−108.80 (19)
B1—O12—C12—C13	109.3 (2)	O41—B2—O42—C42	16.0 (2)
B1—O21—C21—O20	178.7 (2)	O41—C41—C42—O42	12.8 (2)
B1—O21—C21—C22	−1.7 (2)	O41—C41—C42—C43	−109.00 (19)
B1—O22—C22—C21	−16.3 (2)	O42—B2—O31—C31	−125.82 (19)
B1—O22—C22—C23	104.15 (19)	O42—B2—O32—C32	131.51 (18)
O10—C11—C12—O12	−169.3 (2)	O42—B2—O41—C41	−7.7 (2)
O10—C11—C12—C13	67.7 (3)	O42—C42—C43—C44	−175.55 (19)
O11—B1—O12—C12	8.0 (2)	O42—C42—C43—C48	4.1 (3)
O11—B1—O21—C21	111.52 (18)	C31—C32—C33—C34	−80.1 (2)
O11—B1—O22—C22	−101.9 (2)	C31—C32—C33—C38	98.6 (2)
O11—C11—C12—O12	10.9 (2)	C32—C33—C34—C35	179.1 (2)
O11—C11—C12—C13	−112.1 (2)	C32—C33—C38—C37	−179.6 (2)
O12—B1—O11—C11	−0.8 (2)	C33—C34—C35—C36	0.2 (4)
O12—B1—O21—C21	−133.69 (18)	C34—C33—C38—C37	−0.9 (3)
O12—B1—O22—C22	139.96 (18)	C34—C35—C36—C37	−0.3 (4)
O12—C12—C13—C14	170.43 (19)	C35—C36—C37—C38	−0.2 (4)
O12—C12—C13—C18	−11.4 (3)	C36—C37—C38—C33	0.8 (4)
O20—C21—C22—O22	−169.2 (2)	C38—C33—C34—C35	0.4 (3)
O20—C21—C22—C23	68.2 (3)	C41—C42—C43—C44	−58.6 (3)
O21—B1—O11—C11	119.58 (19)	C41—C42—C43—C48	121.1 (2)
O21—B1—O12—C12	−109.20 (19)	C42—C43—C44—C45	179.8 (2)
O21—B1—O22—C22	15.5 (2)	C42—C43—C48—C47	179.8 (2)
O21—C21—C22—O22	11.2 (2)	C43—C44—C45—C46	0.4 (4)
O21—C21—C22—C23	−111.29 (19)	C44—C43—C48—C47	−0.5 (4)
O22—B1—O11—C11	−124.84 (19)	C44—C45—C46—C47	−0.5 (4)
O22—B1—O12—C12	130.40 (19)	C45—C46—C47—C48	0.1 (4)
O22—B1—O21—C21	−8.2 (2)	C46—C47—C48—C43	0.4 (4)
O22—C22—C23—C24	177.55 (18)	C48—C43—C44—C45	0.1 (4)
O22—C22—C23—C28	−4.0 (3)	N1—C51—C52—C53	−169.49 (17)
C11—C12—C13—C14	−71.9 (3)	N1—C55—C56—C57	−178.48 (17)
C11—C12—C13—C18	106.3 (2)	N1—C61—C62—C63	162.59 (19)
C12—C13—C14—C15	177.3 (2)	N1—C65—C66—C67B	165.4 (3)
C12—C13—C18—C17	−178.8 (2)	N1—C65—C66—C67A	−155.6 (3)
C13—C14—C15—C16	1.7 (4)	C51—N1—C55—C56	62.9 (2)
C14—C13—C18—C17	−0.6 (3)	C51—N1—C61—C62	48.5 (2)
C14—C15—C16—C17	−0.9 (4)	C51—N1—C65—C66	−173.26 (18)
C15—C16—C17—C18	−0.6 (4)	C51—C52—C53—C54	77.0 (2)
C16—C17—C18—C13	1.4 (4)	C55—N1—C51—C52	177.62 (16)
C18—C13—C14—C15	−0.9 (4)	C55—N1—C61—C62	−70.1 (2)
C21—C22—C23—C24	−65.0 (2)	C55—N1—C65—C66	−54.2 (2)
C21—C22—C23—C28	113.5 (2)	C55—C56—C57—C58	171.8 (2)
C22—C23—C24—C25	179.5 (2)	C61—N1—C51—C52	59.1 (2)
C22—C23—C28—C27	−179.0 (2)	C61—N1—C55—C56	−176.74 (17)
C23—C24—C25—C26	−0.4 (4)	C61—N1—C65—C66	65.7 (2)
C24—C23—C28—C27	−0.5 (3)	C61—C62—C63—C64	−72.0 (3)
C24—C25—C26—C27	−0.7 (4)	C65—N1—C51—C52	−61.0 (2)
C25—C26—C27—C28	1.2 (4)	C65—N1—C55—C56	−56.1 (2)
C26—C27—C28—C23	−0.6 (4)	C65—N1—C61—C62	167.76 (18)
C28—C23—C24—C25	1.0 (3)	C65—C66—C67B—C68B	71.5 (6)
B2—O31—C31—O30	175.0 (2)	C65—C66—C67A—C68A	−63.1 (5)
B2—O31—C31—C32	−4.7 (2)	N2—C71—C72—C73	−179.89 (16)
B2—O32—C32—C31	−10.4 (2)	N2—C75—C76—C77	167.66 (17)
B2—O32—C32—C33	112.48 (19)	N2—C81—C82—C83	173.92 (18)
B2—O41—C41—O40	177.2 (2)	N2—C85—C86—C87	−176.54 (17)
B2—O41—C41—C42	−3.1 (2)	C71—N2—C75—C76	49.2 (2)
B2—O42—C42—C41	−17.6 (2)	C71—N2—C81—C82	57.0 (2)
B2—O42—C42—C43	102.85 (19)	C71—N2—C85—C86	−174.71 (17)
O30—C31—C32—O32	−170.4 (2)	C71—C72—C73—C74	−176.35 (18)
O30—C31—C32—C33	66.5 (3)	C75—N2—C71—C72	55.9 (2)
O31—B2—O32—C32	7.8 (2)	C75—N2—C81—C82	178.64 (17)
O31—B2—O41—C41	113.18 (18)	C75—N2—C85—C86	64.5 (2)
O31—B2—O42—C42	−101.3 (2)	C75—C76—C77—C78	176.0 (2)
O31—C31—C32—O32	9.3 (2)	C81—N2—C71—C72	175.67 (16)
O31—C31—C32—C33	−113.76 (19)	C81—N2—C75—C76	−71.2 (2)
O32—B2—O31—C31	−1.6 (2)	C81—N2—C85—C86	−54.8 (2)
O32—B2—O41—C41	−132.27 (17)	C81—C82—C83—C84	64.2 (3)
O32—B2—O42—C42	139.94 (18)	C85—N2—C71—C72	−63.2 (2)
O32—C32—C33—C34	161.50 (19)	C85—N2—C75—C76	167.60 (17)
O32—C32—C33—C38	−19.8 (3)	C85—N2—C81—C82	−61.8 (2)
O40—C41—C42—O42	−167.4 (2)	C85—C86—C87—C88	−179.8 (2)