A polycyclic condensate of phenyl­boronic and boric acids with N-hydroxy­piperidine

1-Hydro­xy­piperidinium 16-hydroxy-6,6-penta­methyl­ene-11,13,19-tri­phenyl-19-(1-piperidiniumoxy)-8,10,12,14,15,17,18,20-octaoxa-6-azonia-11,13,16-tribora-7,9,19-triboratatri­spiro[5.0.1.5.3.3]­icosane diethyl ether hemisolvate, C₃₃H₄₉B₆N₃O₁₁·0.5C₄H₁₀O, contains a tetracyclic ring system, with two boroxine, a BOBON, and a piperidinium ring spiro-fused; the diethyl ether solvent mol­ecule is disordered over an inversion centre.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in solvent or counterion
• R factor = 0.043
• wR factor = 0.102
• Data-to-parameter ratio = 16.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.87
         From the CIF: _reflns_number_total               8500
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         9876
         Completeness (_total/calc)             86.07%
          Alert B: < 90% complete (theta max?)

PLAT_213  Alert B Atom C2      has ADP max/min Ratio ...........       4.10 prolate


 Alert Level C:



PLAT_302  Alert C Anion/Solvent Disorder .......................      14.00 Perc.


 0 Alert Level A = Potentially serious problem

 2 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

Computing details

Data collection: D*TREK (Molecular Structure Corporation, 1997); cell refinement: D*TREK; data reduction: TEXSAN (Molecular Structure Corporation, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: TEXSAN; software used to prepare material for publication: TEXSAN.

(II)

Crystal data

C5H12NO^+·C28H37B6N2O10^−·0.5C4H10O	Z = 2
Mr = 765.68	F(000) = 814
Triclinic, P1	Dx = 1.226 Mg m^−3
a = 10.636 (2) Å	Mo Kα radiation, λ = 0.7107 Å
b = 15.340 (2) Å	Cell parameters from 9653 reflections
c = 15.545 (2) Å	θ = 2.3–27.9°
α = 105.467 (2)°	µ = 0.09 mm^−1
β = 107.949 (4)°	T = 173 K
γ = 109.453 (2)°	Chip, colorless
V = 2073.3 (5) Å^3	0.40 × 0.30 × 0.20 mm

Data collection

Quantum CCD diffractometer	8500 independent reflections
Radiation source: X-ray tube	5491 reflections with I > 3σ(I)
Graphite monochromator	Rint = 0.038
CCD scans	θmax = 27.9°, θmin = 2.3°
Absorption correction: multi-scan d*TREK (Molecular Structure Corporation, 1997)	h = −12→13
Tmin = 0.96, Tmax = 0.98	k = −19→17
19307 measured reflections	l = −20→18

Refinement

Refinement on F^2	2 restraints
Least-squares matrix: full	0 constraints
R[F^2 > 2σ(F^2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.102	Weighting scheme based on measured s.u.'s w = 1/[σ^2(Fo^2)]
S = 1.41	(Δ/σ)max = 0.036
8500 reflections	Δρmax = 0.49 e Å^−3
527 parameters	Δρmin = −0.49 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	−0.0879 (1)	0.66068 (7)	0.68249 (6)	0.0194 (2)
O2	−0.0982 (1)	0.55593 (7)	0.77181 (7)	0.0231 (3)
O3	0.1269 (1)	0.63697 (7)	0.76185 (6)	0.0189 (2)
O4	0.1590 (1)	0.77887 (6)	0.72005 (6)	0.0171 (2)
O5	0.1453 (1)	0.74887 (7)	0.55634 (6)	0.0290 (3)
O6	0.0380 (1)	0.60865 (6)	0.59149 (6)	0.0202 (2)
O7	0.3276 (1)	0.90565 (6)	0.69225 (6)	0.0176 (2)
O8	0.1628 (1)	0.95341 (7)	0.59987 (7)	0.0278 (3)
O9	0.3822 (1)	0.97103 (7)	0.57224 (6)	0.0281 (3)
O10	0.0598 (1)	0.58618 (8)	0.44014 (7)	0.0351 (3)
O11	0.5066 (1)	0.93379 (7)	0.86520 (7)	0.0315 (3)
O12	1.0000	1.0000	1.0000	0.0953 (9)
N1	0.0808 (1)	0.88197 (9)	0.63036 (8)	0.0253 (3)
N2	0.3244 (1)	0.86917 (8)	0.50256 (8)	0.0217 (3)
N3	0.4239 (1)	0.83355 (8)	0.85447 (8)	0.0211 (3)
C1	−0.0709 (2)	0.8169 (1)	0.5477 (1)	0.0469 (5)
C2	−0.1631 (2)	0.8770 (2)	0.5360 (2)	0.0813 (7)
C3	−0.1666 (3)	0.9289 (2)	0.6330 (2)	0.0829 (8)
C4	−0.0114 (2)	0.9976 (2)	0.7093 (2)	0.0638 (7)
C5	0.0753 (2)	0.9380 (1)	0.7228 (1)	0.0348 (5)
C6	0.2447 (2)	0.8589 (1)	0.40064 (9)	0.0270 (4)
C7	0.1817 (2)	0.7499 (1)	0.3279 (1)	0.0325 (4)
C8	0.3017 (2)	0.7165 (1)	0.3346 (1)	0.0348 (4)
C9	0.3876 (2)	0.7327 (1)	0.4404 (1)	0.0324 (4)
C10	0.4482 (2)	0.8420 (1)	0.5118 (1)	0.0297 (4)
C11	−0.3313 (2)	0.5700 (1)	0.6890 (1)	0.0226 (4)
C12	−0.4116 (2)	0.6008 (1)	0.6245 (1)	0.0305 (4)
C13	−0.5615 (2)	0.5704 (1)	0.5967 (1)	0.0393 (5)
C14	−0.6348 (2)	0.5081 (1)	0.6330 (1)	0.0410 (5)
C15	−0.5595 (2)	0.4763 (1)	0.6963 (1)	0.0420 (5)
C16	−0.4092 (2)	0.5070 (1)	0.7245 (1)	0.0327 (5)
C17	0.1155 (2)	0.5202 (1)	0.85116 (9)	0.0191 (3)
C18	0.0461 (2)	0.4690 (1)	0.8983 (1)	0.0259 (4)
C19	0.1084 (2)	0.4206 (1)	0.9495 (1)	0.0343 (4)
C20	0.2395 (2)	0.4213 (1)	0.9535 (1)	0.0390 (5)
C21	0.3097 (2)	0.4700 (1)	0.9067 (1)	0.0377 (5)
C22	0.2482 (2)	0.5192 (1)	0.8565 (1)	0.0282 (4)
C23	0.4291 (2)	1.0954 (1)	0.73009 (9)	0.0196 (3)
C24	0.5754 (2)	1.1257 (1)	0.7946 (1)	0.0289 (4)
C25	0.6664 (2)	1.2242 (1)	0.8673 (1)	0.0402 (4)
C26	0.6144 (2)	1.2953 (1)	0.8766 (1)	0.0442 (4)
C27	0.4717 (2)	1.2683 (1)	0.8136 (1)	0.0403 (5)
C28	0.3802 (2)	1.1695 (1)	0.7409 (1)	0.0277 (4)
C29	0.4366 (2)	0.8381 (1)	0.9535 (1)	0.0274 (4)
C30	0.5919 (2)	0.8637 (1)	1.0215 (1)	0.0369 (4)
C31	0.6393 (2)	0.7879 (1)	0.9754 (1)	0.0491 (5)
C32	0.6288 (2)	0.7857 (1)	0.8749 (1)	0.0456 (5)
C33	0.4750 (2)	0.7631 (1)	0.8071 (1)	0.0307 (4)
C34	0.9342 (5)	1.0770 (5)	0.9740 (4)	0.092 (2)	0.500
C35	0.9394 (4)	1.1391 (3)	1.0490 (3)	0.130 (1)
C36	1.0100 (6)	0.9432 (5)	0.9389 (5)	0.105 (2)	0.500
B1	−0.1643 (2)	0.5989 (1)	0.7150 (1)	0.0193 (4)
B2	0.0468 (2)	0.5745 (1)	0.7922 (1)	0.0173 (4)
B3	0.0575 (2)	0.6723 (1)	0.6893 (1)	0.0171 (4)
B4	0.1826 (2)	0.8220 (1)	0.6529 (1)	0.0184 (4)
B5	0.0795 (2)	0.6459 (1)	0.5298 (1)	0.0217 (4)
B6	0.3248 (2)	0.9794 (1)	0.6504 (1)	0.0198 (4)
H1	−0.0629	0.7910	0.4858	0.056*
H2	−0.1219	0.7596	0.5613	0.056*
H3	−0.1191	0.9285	0.5139	0.097*
H4	−0.2650	0.8297	0.4859	0.097*
H5	−0.2216	0.9683	0.6235	0.100*
H6	−0.2145	0.8778	0.6542	0.100*
H7	0.0355	1.0492	0.6880	0.077*
H8	−0.0117	1.0308	0.7724	0.077*
H9	0.0295	0.8885	0.7464	0.042*
H10	0.1772	0.9852	0.7728	0.042*
H11	0.1639	0.8772	0.3972	0.032*
H12	0.3137	0.9041	0.3839	0.032*
H13	0.1085	0.7058	0.3428	0.039*
H14	0.1333	0.7441	0.2604	0.039*
H15	0.2563	0.6444	0.2910	0.042*
H16	0.3699	0.7562	0.3137	0.042*
H17	0.3215	0.6878	0.4590	0.039*
H18	0.4702	0.7164	0.4443	0.039*
H19	0.5189	0.8869	0.4959	0.035*
H20	0.4983	0.8499	0.5799	0.035*
H21	−0.3606	0.6450	0.5983	0.036*
H22	−0.6152	0.5930	0.5513	0.047*
H23	−0.7407	0.4866	0.6136	0.049*
H24	−0.6119	0.4318	0.7217	0.050*
H25	−0.3566	0.4840	0.7701	0.039*
H26	−0.0481	0.4672	0.8953	0.031*
H27	0.0583	0.3859	0.9827	0.041*
H28	0.2831	0.3872	0.9896	0.047*
H29	0.4029	0.4701	0.9088	0.045*
H30	0.2994	0.5540	0.8238	0.034*
H31	0.6151	1.0763	0.7885	0.035*
H32	0.7682	1.2428	0.9121	0.048*
H33	0.6785	1.3647	0.9277	0.053*
H34	0.4337	1.3186	0.8195	0.048*
H35	0.2788	1.1518	0.6964	0.033*
H36	0.4103	0.8902	0.9832	0.033*
H37	0.3681	0.7720	0.9457	0.033*
H38	0.6598	0.9318	1.0331	0.044*
H39	0.5952	0.8623	1.0848	0.044*
H40	0.7420	0.8075	1.0192	0.059*
H41	0.5746	0.7204	0.9668	0.059*
H42	0.6995	0.8518	0.8844	0.055*
H43	0.6533	0.7330	0.8442	0.055*
H44	0.4064	0.6934	0.7906	0.037*
H45	0.4753	0.7700	0.7463	0.037*
H46	0.320 (2)	0.811 (1)	0.810 (1)	0.025 (4)*
H47	0.435 (2)	0.929 (2)	0.792 (2)	0.088 (7)*
H48	0.257 (2)	0.824 (1)	0.518 (1)	0.031 (4)*
H49	0.029 (2)	0.524 (2)	0.434 (1)	0.066 (6)*
H50	0.9908	1.1152	0.9462	0.109*	0.500
H51	0.8295	1.0360	0.9239	0.109*	0.500
H52	1.0408	1.1807	1.0986	0.156*	0.500
H53	0.8972	1.1830	1.0280	0.156*	0.500
H54	0.8789	1.1018	1.0758	0.156*	0.500
H55	0.9159	0.9050	0.8849	0.136*	0.500
H56	1.0849	0.9851	0.9248	0.136*	0.500
H57	1.0103	1.1896	1.0382	0.156*	0.500
H58	0.9312	1.1723	1.1088	0.156*	0.500
H59	0.8405	1.1077	0.9913	0.156*	0.500

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0194 (5)	0.0194 (5)	0.0248 (5)	0.0088 (4)	0.0115 (4)	0.0144 (4)
O2	0.0229 (5)	0.0262 (5)	0.0324 (5)	0.0129 (4)	0.0170 (4)	0.0211 (4)
O3	0.0186 (5)	0.0172 (5)	0.0244 (5)	0.0075 (4)	0.0101 (4)	0.0132 (4)
O4	0.0215 (5)	0.0102 (4)	0.0169 (4)	0.0034 (4)	0.0087 (4)	0.0062 (3)
O5	0.0472 (7)	0.0098 (5)	0.0215 (5)	0.0011 (4)	0.0192 (4)	0.0046 (4)
O6	0.0268 (6)	0.0105 (4)	0.0209 (4)	0.0033 (4)	0.0133 (4)	0.0065 (4)
O7	0.0197 (5)	0.0106 (4)	0.0213 (4)	0.0043 (4)	0.0085 (4)	0.0087 (4)
O8	0.0235 (5)	0.0195 (5)	0.0322 (5)	0.0024 (4)	0.0034 (4)	0.0187 (4)
O9	0.0425 (7)	0.0084 (4)	0.0235 (5)	0.0002 (4)	0.0179 (4)	0.0033 (4)
O10	0.0609 (8)	0.0113 (5)	0.0289 (5)	0.0038 (5)	0.0298 (5)	0.0063 (4)
O11	0.0329 (6)	0.0176 (5)	0.0298 (5)	0.0027 (5)	0.0040 (5)	0.0124 (4)
O12	0.065 (2)	0.098 (2)	0.076 (2)	0.013 (1)	0.015 (1)	0.020 (1)
N1	0.0185 (6)	0.0190 (6)	0.0307 (6)	0.0024 (5)	0.0038 (5)	0.0154 (5)
N2	0.0299 (7)	0.0092 (5)	0.0190 (5)	0.0017 (5)	0.0114 (5)	0.0043 (4)
N3	0.0204 (7)	0.0163 (6)	0.0217 (5)	0.0047 (5)	0.0061 (5)	0.0090 (5)
C1	0.0234 (9)	0.038 (1)	0.052 (1)	−0.0047 (7)	−0.0066 (7)	0.0294 (8)
C2	0.020 (1)	0.073 (2)	0.131 (2)	0.004 (1)	−0.008 (1)	0.084 (1)
C3	0.048 (1)	0.073 (2)	0.164 (2)	0.042 (1)	0.047 (1)	0.079 (2)
C4	0.047 (1)	0.044 (1)	0.131 (2)	0.0333 (9)	0.050 (1)	0.050 (1)
C5	0.037 (1)	0.0294 (9)	0.0525 (9)	0.0210 (8)	0.0283 (8)	0.0195 (7)
C6	0.0361 (9)	0.0183 (7)	0.0216 (6)	0.0084 (7)	0.0092 (6)	0.0100 (6)
C7	0.043 (1)	0.0198 (7)	0.0216 (7)	0.0058 (7)	0.0101 (7)	0.0060 (6)
C8	0.049 (1)	0.0180 (7)	0.0365 (8)	0.0078 (7)	0.0280 (7)	0.0082 (6)
C9	0.037 (1)	0.0235 (8)	0.0469 (8)	0.0146 (7)	0.0261 (7)	0.0190 (7)
C10	0.0279 (9)	0.0251 (8)	0.0318 (8)	0.0070 (7)	0.0112 (6)	0.0141 (6)
C11	0.0256 (8)	0.0214 (7)	0.0274 (7)	0.0126 (6)	0.0168 (6)	0.0108 (6)
C12	0.0292 (8)	0.0383 (9)	0.0350 (8)	0.0186 (7)	0.0181 (7)	0.0215 (7)
C13	0.0297 (9)	0.054 (1)	0.0427 (9)	0.0256 (9)	0.0141 (7)	0.0249 (8)
C14	0.0227 (9)	0.047 (1)	0.055 (1)	0.0169 (8)	0.0198 (8)	0.0181 (8)
C15	0.0331 (9)	0.047 (1)	0.070 (1)	0.0227 (8)	0.0366 (9)	0.0359 (9)
C16	0.0319 (9)	0.0380 (9)	0.0512 (9)	0.0224 (8)	0.0283 (8)	0.0301 (8)
C17	0.0230 (7)	0.0126 (6)	0.0167 (6)	0.0054 (6)	0.0066 (5)	0.0049 (5)
C18	0.0262 (8)	0.0215 (7)	0.0244 (7)	0.0056 (6)	0.0079 (6)	0.0119 (6)
C19	0.044 (1)	0.0266 (8)	0.0315 (8)	0.0117 (7)	0.0124 (7)	0.0205 (7)
C20	0.049 (1)	0.0309 (9)	0.0383 (8)	0.0239 (8)	0.0091 (8)	0.0207 (7)
C21	0.043 (1)	0.043 (1)	0.0433 (9)	0.0313 (9)	0.0196 (8)	0.0239 (8)
C22	0.0326 (9)	0.0280 (8)	0.0313 (8)	0.0172 (7)	0.0158 (7)	0.0156 (6)
C23	0.0259 (8)	0.0135 (6)	0.0166 (6)	0.0035 (6)	0.0101 (5)	0.0082 (5)
C24	0.0279 (8)	0.0208 (7)	0.0294 (7)	0.0025 (6)	0.0093 (6)	0.0130 (6)
C25	0.034 (1)	0.0318 (9)	0.0244 (7)	−0.0084 (7)	0.0024 (6)	0.0109 (6)
C26	0.063 (1)	0.0174 (8)	0.0235 (8)	−0.0065 (8)	0.0176 (7)	0.0006 (6)
C27	0.068 (1)	0.0165 (7)	0.0425 (9)	0.0161 (8)	0.0342 (8)	0.0123 (7)
C28	0.0381 (9)	0.0171 (7)	0.0280 (7)	0.0098 (6)	0.0161 (6)	0.0108 (6)
C29	0.0312 (8)	0.0269 (8)	0.0223 (7)	0.0092 (7)	0.0122 (6)	0.0118 (6)
C30	0.0323 (9)	0.0372 (9)	0.0275 (8)	0.0049 (7)	0.0034 (6)	0.0193 (7)
C31	0.028 (1)	0.048 (1)	0.065 (1)	0.0172 (9)	0.0061 (8)	0.0327 (9)
C32	0.0321 (9)	0.042 (1)	0.066 (1)	0.0212 (9)	0.0242 (8)	0.0179 (9)
C33	0.0340 (9)	0.0249 (8)	0.0335 (8)	0.0138 (7)	0.0175 (7)	0.0083 (6)
C34	0.035 (2)	0.142 (4)	0.089 (3)	0.008 (3)	0.013 (2)	0.091 (3)
C35	0.087 (2)	0.134 (3)	0.144 (3)	0.042 (2)	0.039 (2)	0.044 (3)
C36	0.032 (3)	0.088 (4)	0.143 (6)	0.004 (3)	0.044 (3)	−0.001 (3)
B1	0.0251 (8)	0.0171 (8)	0.0187 (7)	0.0106 (7)	0.0117 (6)	0.0080 (6)
B2	0.0210 (8)	0.0131 (7)	0.0163 (7)	0.0062 (6)	0.0088 (6)	0.0051 (6)
B3	0.0197 (8)	0.0135 (7)	0.0181 (7)	0.0053 (6)	0.0091 (6)	0.0081 (6)
B4	0.0224 (8)	0.0117 (7)	0.0183 (7)	0.0046 (6)	0.0087 (6)	0.0064 (5)
B5	0.0259 (9)	0.0122 (7)	0.0225 (7)	0.0026 (7)	0.0124 (7)	0.0066 (6)
B6	0.0240 (8)	0.0125 (7)	0.0187 (7)	0.0045 (6)	0.0074 (6)	0.0078 (5)

Geometric parameters (Å, º)

O1—B1	1.345 (2)	C11—C16	1.399 (2)
O1—B3	1.464 (2)	C11—B1	1.567 (2)
O2—B1	1.394 (2)	C12—C13	1.385 (2)
O2—B2	1.385 (2)	C12—H21	0.98
O3—B2	1.347 (2)	C13—C14	1.380 (3)
O3—B3	1.480 (2)	C13—H22	0.98
O4—B3	1.468 (2)	C14—C15	1.370 (3)
O4—B4	1.418 (2)	C14—H23	0.98
O5—B4	1.452 (2)	C15—C16	1.388 (3)
O5—B5	1.376 (2)	C15—H24	0.98
O6—B3	1.479 (2)	C16—H25	0.98
O6—B5	1.352 (2)	C17—C18	1.397 (2)
O7—B4	1.443 (2)	C17—C22	1.393 (2)
O7—B6	1.451 (2)	C17—B2	1.571 (2)
O8—N1	1.443 (2)	C18—C19	1.394 (2)
O8—B6	1.512 (2)	C18—H26	0.98
O9—N2	1.428 (2)	C19—C20	1.372 (3)
O9—B6	1.514 (2)	C19—H27	0.98
O10—B5	1.355 (2)	C20—C21	1.379 (3)
O10—H49	0.87 (3)	C20—H28	0.98
O11—N3	1.428 (2)	C21—C22	1.391 (3)
O11—H47	1.12 (3)	C21—H29	0.98
O12—C34	1.636 (8)	C22—H30	0.98
O12—C36	1.16 (1)	C23—C24	1.397 (2)
N1—C1	1.488 (2)	C23—C28	1.391 (2)
N1—C5	1.494 (2)	C23—B6	1.611 (2)
N1—B4	1.656 (2)	C24—C25	1.392 (2)
N2—C6	1.484 (2)	C24—H31	0.98
N2—C10	1.486 (2)	C25—C26	1.372 (3)
N2—H48	0.96 (2)	C25—H32	0.98
N3—C29	1.484 (2)	C26—C27	1.373 (3)
N3—C33	1.490 (2)	C26—H33	0.98
N3—H46	0.98 (2)	C27—C28	1.395 (2)
C1—C2	1.558 (4)	C27—H34	0.98
C1—H1	0.98	C28—H35	0.98
C1—H2	0.98	C29—C30	1.506 (3)
C2—C3	1.524 (4)	C29—H36	0.98
C2—H3	0.98	C29—H37	0.98
C2—H4	0.98	C30—C31	1.513 (3)
C3—C4	1.487 (4)	C30—H38	0.98
C3—H5	0.98	C30—H39	0.98
C3—H6	0.98	C31—C32	1.521 (3)
C4—C5	1.508 (3)	C31—H40	0.98
C4—H7	0.98	C31—H41	0.98
C4—H8	0.98	C32—C33	1.507 (3)
C5—H9	0.98	C32—H42	0.98
C5—H10	0.98	C32—H43	0.98
C6—C7	1.517 (2)	C33—H44	0.98
C6—H11	0.98	C33—H45	0.98
C6—H12	0.98	C34—C35	1.267 (8)
C7—C8	1.512 (3)	C34—H50	0.98
C7—H13	0.98	C34—H51	0.99
C7—H14	0.98	C35—C36^i	1.56 (1)
C8—C9	1.518 (3)	C35—H52	0.96
C8—H15	0.98	C35—H53	0.99
C8—H16	0.98	C35—H54	0.98
C9—C10	1.519 (2)	C35—H57	0.98
C9—H17	0.98	C35—H58	0.98
C9—H18	0.98	C35—H59	1.00
C10—H19	0.98	C36—H55	0.94
C10—H20	0.98	C36—H56	0.97
C11—C12	1.397 (2)
O3···N3	3.111 (2)	O10···B3^ii	3.497 (2)
O3···C33	3.293 (2)	O10···B5^ii	3.590 (2)
O3···O10^ii	3.379 (2)	O11···C24	3.346 (2)
O3···C29	3.395 (2)	O11···B4	3.427 (2)
O4···N3	2.621 (2)	O11···C29^iii	3.582 (2)
O4···O11	3.249 (2)	N3···B4	3.299 (2)
O4···C33	3.332 (2)	N3···B3	3.452 (2)
O4···C29	3.545 (2)	C3···C10^iv	3.518 (3)
O6···O10^ii	2.662 (2)	C7···C18^ii	3.541 (2)
O6···O6^ii	3.404 (2)	C8···C25^v	3.574 (2)
O6···B5^ii	3.426 (2)	C12···C13^vi	3.589 (3)
O7···O11	2.592 (2)	C13···C33^iv	3.590 (3)
O7···N3	3.046 (2)	C18···C18^vii	3.577 (3)
O10···B2^ii	3.358 (2)	C25···C29^iii	3.531 (2)
B1—O1—B3	122.1 (1)	C19—C18—H26	119.4
B1—O2—B2	119.4 (1)	C18—C19—C20	120.2 (2)
B2—O3—B3	121.8 (1)	C18—C19—H27	119.9
B3—O4—B4	123.9 (1)	C20—C19—H27	119.9
B4—O5—B5	122.4 (1)	C19—C20—C21	119.9 (2)
B3—O6—B5	124.0 (1)	C19—C20—H28	120.1
B4—O7—B6	112.2 (1)	C21—C20—H28	120.0
N1—O8—B6	108.3 (1)	C20—C21—C22	119.8 (2)
N2—O9—B6	113.5 (1)	C20—C21—H29	120.1
B5—O10—H49	109 (1)	C22—C21—H29	120.1
N3—O11—H47	99 (1)	C17—C22—C21	121.8 (2)
C34—O12—C36	119.9 (5)	C17—C22—H30	119.1
O8—N1—C1	107.8 (1)	C21—C22—H30	119.1
O8—N1—C5	109.7 (1)	C24—C23—C28	116.5 (1)
O8—N1—B4	102.4 (1)	C24—C23—B6	120.3 (2)
C1—N1—C5	111.1 (2)	C28—C23—B6	123.2 (2)
C1—N1—B4	114.7 (1)	C23—C24—C25	121.8 (2)
C5—N1—B4	110.8 (1)	C23—C24—H31	119.1
O9—N2—C6	109.9 (1)	C25—C24—H31	119.1
O9—N2—C10	109.0 (1)	C24—C25—C26	120.3 (2)
O9—N2—H48	109 (1)	C24—C25—H32	119.8
C6—N2—C10	111.7 (1)	C26—C25—H32	119.9
C6—N2—H48	109 (1)	C25—C26—C27	119.3 (2)
C10—N2—H48	108 (1)	C25—C26—H33	120.4
O11—N3—C29	108.3 (1)	C27—C26—H33	120.3
O11—N3—C33	110.5 (1)	C26—C27—C28	120.4 (2)
O11—N3—H46	107 (1)	C26—C27—H34	119.9
C29—N3—C33	113.1 (1)	C28—C27—H34	119.7
C29—N3—H46	109.6 (9)	C23—C28—C27	121.7 (2)
C33—N3—H46	108 (1)	C23—C28—H35	119.2
N1—C1—C2	111.6 (2)	C27—C28—H35	119.1
N1—C1—H1	108.9	N3—C29—C30	111.3 (1)
N1—C1—H2	108.9	N3—C29—H36	109.0
C2—C1—H1	109.0	N3—C29—H37	109.1
C2—C1—H2	109.0	C30—C29—H36	109.0
H1—C1—H2	109.3	C30—C29—H37	109.0
C1—C2—C3	112.0 (2)	H36—C29—H37	109.4
C1—C2—H3	108.8	C29—C30—C31	110.4 (2)
C1—C2—H4	108.7	C29—C30—H38	109.2
C3—C2—H3	109.0	C29—C30—H39	109.2
C3—C2—H4	108.9	C31—C30—H38	109.2
H3—C2—H4	109.4	C31—C30—H39	109.3
C2—C3—C4	108.3 (2)	H38—C30—H39	109.5
C2—C3—H5	109.6	C30—C31—C32	110.2 (2)
C2—C3—H6	109.7	C30—C31—H40	109.3
C4—C3—H5	109.8	C30—C31—H41	109.3
C4—C3—H6	109.8	C32—C31—H40	109.3
H5—C3—H6	109.7	C32—C31—H41	109.4
C3—C4—C5	110.2 (2)	H40—C31—H41	109.4
C3—C4—H7	109.4	C31—C32—C33	111.2 (2)
C3—C4—H8	109.3	C31—C32—H42	109.1
C5—C4—H7	109.3	C31—C32—H43	109.1
C5—C4—H8	109.3	C33—C32—H42	109.0
H7—C4—H8	109.4	C33—C32—H43	109.0
N1—C5—C4	114.1 (2)	H42—C32—H43	109.5
N1—C5—H9	108.3	N3—C33—C32	111.8 (1)
N1—C5—H10	108.2	N3—C33—H44	108.9
C4—C5—H9	108.3	N3—C33—H45	108.9
C4—C5—H10	108.4	C32—C33—H44	108.9
H9—C5—H10	109.4	C32—C33—H45	108.9
N2—C6—C7	109.2 (1)	H44—C33—H45	109.5
N2—C6—H11	109.5	O12—C34—C35	113.0 (4)
N2—C6—H12	109.6	O12—C34—H50	109.3
C7—C6—H11	109.6	O12—C34—H51	108.5
C7—C6—H12	109.6	C35—C34—H50	108.6
H11—C6—H12	109.4	C35—C34—H51	108.4
C6—C7—C8	111.4 (1)	H50—C34—H51	108.9
C6—C7—H13	109.0	C34—C35—H52	110.0
C6—C7—H14	109.0	C34—C35—H53	108.8
C8—C7—H13	109.0	C34—C35—H54	109.6
C8—C7—H14	109.0	C36^i—C35—H57	110.6
H13—C7—H14	109.4	C36^i—C35—H58	109.3
C7—C8—C9	110.5 (1)	C36^i—C35—H59	110.6
C7—C8—H15	109.3	H52—C35—H53	109.5
C7—C8—H16	109.2	H52—C35—H54	110.7
C9—C8—H15	109.2	H53—C35—H54	108.2
C9—C8—H16	109.1	H57—C35—H58	109.8
H15—C8—H16	109.5	H57—C35—H59	108.3
C8—C9—C10	110.8 (1)	H58—C35—H59	108.2
C8—C9—H17	109.1	O12—C36—C35^i	125.5 (8)
C8—C9—H18	109.1	O12—C36—H55	107.1
C10—C9—H17	109.2	O12—C36—H56	105.1
C10—C9—H18	109.1	C35^i—C36—H55	103.0
H17—C9—H18	109.5	C35^i—C36—H56	102.2
N2—C10—C9	109.6 (1)	H55—C36—H56	114.3
N2—C10—H19	109.4	O1—B1—O2	121.1 (2)
N2—C10—H20	109.4	O1—B1—C11	121.8 (2)
C9—C10—H19	109.5	O2—B1—C11	117.1 (1)
C9—C10—H20	109.4	O2—B2—O3	121.0 (2)
H19—C10—H20	109.5	O2—B2—C17	118.4 (1)
C12—C11—C16	117.0 (2)	O3—B2—C17	120.6 (2)
C12—C11—B1	121.5 (1)	O1—B3—O3	111.7 (1)
C16—C11—B1	121.4 (2)	O1—B3—O4	111.1 (1)
C11—C12—C13	121.7 (2)	O1—B3—O6	108.6 (1)
C11—C12—H21	119.2	O3—B3—O4	107.8 (1)
C13—C12—H21	119.1	O3—B3—O6	107.1 (1)
C12—C13—C14	119.8 (2)	O4—B3—O6	110.5 (1)
C12—C13—H22	120.1	O4—B4—O5	114.3 (1)
C14—C13—H22	120.2	O4—B4—O7	114.5 (1)
C13—C14—C15	120.1 (2)	O4—B4—N1	111.5 (1)
C13—C14—H23	120.0	O5—B4—O7	110.7 (1)
C15—C14—H23	120.0	O5—B4—N1	105.4 (1)
C14—C15—C16	120.2 (2)	O7—B4—N1	99.0 (1)
C14—C15—H24	119.9	O5—B5—O6	120.4 (1)
C16—C15—H24	119.9	O5—B5—O10	116.4 (1)
C11—C16—C15	121.3 (2)	O6—B5—O10	123.1 (1)
C11—C16—H25	119.4	O7—B6—O8	105.1 (1)
C15—C16—H25	119.3	O7—B6—O9	112.8 (1)
C18—C17—C22	117.0 (2)	O7—B6—C23	113.8 (1)
C18—C17—B2	122.2 (2)	O8—B6—O9	107.6 (1)
C22—C17—B2	120.8 (1)	O8—B6—C23	114.1 (1)
C17—C18—C19	121.3 (2)	O9—B6—C23	103.5 (1)
C17—C18—H26	119.3
O1—B1—O2—B2	−2.2 (2)	N1—O8—B6—C23	−113.5 (1)
O1—B1—C11—C12	5.1 (2)	N1—C1—C2—C3	−53.6 (3)
O1—B1—C11—C16	−178.9 (2)	N1—C5—C4—C3	58.7 (3)
O1—B3—O3—B2	19.0 (2)	N1—B4—O4—B3	97.4 (2)
O1—B3—O4—B4	−95.1 (2)	N1—B4—O5—B5	−117.0 (2)
O1—B3—O6—B5	108.1 (2)	N1—B4—O7—B6	−29.9 (1)
O2—B1—O1—B3	11.0 (2)	N2—O9—B6—C23	169.0 (1)
O2—B1—C11—C12	−173.6 (1)	N2—C6—C7—C8	−57.0 (2)
O2—B1—C11—C16	2.3 (2)	N2—C10—C9—C8	56.8 (2)
O2—B2—O3—B3	−12.4 (2)	N3—C29—C30—C31	−56.6 (2)
O2—B2—C17—C18	−11.6 (2)	N3—C33—C32—C31	53.2 (2)
O2—B2—C17—C22	166.9 (1)	C1—N1—O8—B6	−150.2 (1)
O3—B2—O2—B1	3.0 (2)	C1—N1—C5—C4	−53.2 (2)
O3—B2—C17—C18	168.9 (1)	C1—C2—C3—C4	57.7 (3)
O3—B2—C17—C22	−12.6 (2)	C2—C1—N1—C5	49.4 (2)
O3—B3—O1—B1	−18.3 (2)	C2—C1—N1—B4	176.0 (2)
O3—B3—O4—B4	142.2 (1)	C2—C3—C4—C5	−59.1 (3)
O3—B3—O6—B5	−131.2 (2)	C4—C5—N1—B4	178.1 (2)
O4—B3—O1—B1	−138.7 (1)	C5—N1—O8—B6	88.8 (2)
O4—B3—O3—B2	141.3 (1)	C6—N2—O9—B6	120.9 (1)
O4—B3—O6—B5	−14.0 (2)	C6—N2—C10—C9	−60.2 (2)
O4—B4—O5—B5	5.9 (2)	C6—C7—C8—C9	55.0 (2)
O4—B4—O7—B6	−148.6 (1)	C7—C6—N2—C10	59.9 (2)
O4—B4—N1—O8	156.2 (1)	C7—C8—C9—C10	−54.7 (2)
O4—B4—N1—C1	−87.4 (2)	C10—N2—O9—B6	−116.4 (1)
O4—B4—N1—C5	39.3 (2)	C11—C12—C13—C14	0.0 (3)
O5—B4—O4—B3	−22.1 (2)	C11—C16—C15—C14	−0.4 (3)
O5—B4—O7—B6	80.4 (2)	C11—B1—O1—B3	−167.7 (1)
O5—B4—N1—O8	−79.2 (1)	C11—B1—O2—B2	176.5 (1)
O5—B4—N1—C1	37.2 (2)	C12—C11—C16—C15	0.2 (3)
O5—B4—N1—C5	163.9 (1)	C12—C13—C14—C15	−0.1 (3)
O5—B5—O6—B3	0.4 (3)	C13—C12—C11—C16	−0.1 (3)
O6—B3—O1—B1	99.6 (2)	C13—C12—C11—B1	176.0 (2)
O6—B3—O3—B2	−99.8 (2)	C13—C14—C15—C16	0.3 (3)
O6—B3—O4—B4	25.4 (2)	C15—C16—C11—B1	−175.9 (2)
O6—B5—O5—B4	4.4 (3)	C17—C18—C19—C20	−0.9 (3)
O7—B4—O4—B3	−151.2 (1)	C17—C22—C21—C20	−0.5 (3)
O7—B4—O5—B5	136.9 (2)	C17—B2—O2—B1	−176.5 (1)
O7—B4—N1—O8	35.2 (1)	C17—B2—O3—B3	167.1 (1)
O7—B4—N1—C1	151.6 (1)	C18—C17—C22—C21	−0.3 (2)
O7—B4—N1—C5	−81.6 (1)	C18—C19—C20—C21	0.0 (3)
O7—B6—O8—N1	11.9 (2)	C19—C18—C17—C22	1.0 (2)
O7—B6—O9—N2	45.6 (2)	C19—C18—C17—B2	179.5 (1)
O7—B6—C23—C24	48.2 (2)	C19—C20—C21—C22	0.7 (3)
O7—B6—C23—C28	−130.1 (2)	C21—C22—C17—B2	−178.8 (2)
O8—N1—C1—C2	−70.7 (2)	C23—C24—C25—C26	−1.0 (3)
O8—N1—C5—C4	65.8 (2)	C23—C28—C27—C26	0.3 (3)
O8—B6—O7—B4	14.0 (2)	C23—B6—O7—B4	139.5 (1)
O8—B6—O9—N2	−69.9 (2)	C24—C23—C28—C27	−1.1 (2)
O8—B6—C23—C24	168.8 (1)	C24—C25—C26—C27	0.2 (3)
O8—B6—C23—C28	−9.4 (2)	C25—C24—C23—C28	1.4 (2)
O9—N2—C6—C7	−179.0 (1)	C25—C24—C23—B6	−177.0 (1)
O9—N2—C10—C9	178.2 (1)	C25—C26—C27—C28	0.2 (3)
O9—B6—O7—B4	−103.0 (1)	C27—C28—C23—B6	177.2 (1)
O9—B6—O8—N1	132.3 (1)	C29—N3—C33—C32	−52.7 (2)
O9—B6—C23—C24	−74.6 (2)	C29—C30—C31—C32	57.5 (2)
O9—B6—C23—C28	107.1 (2)	C30—C29—N3—C33	54.4 (2)
O10—B5—O5—B4	−175.6 (2)	C30—C31—C32—C33	−56.0 (2)
O10—B5—O6—B3	−179.6 (2)	C34—O12—C36—C35^i	−175.7 (4)
O11—N3—C29—C30	−68.5 (2)	C35—C34—O12—C36	−175.3 (5)
O11—N3—C33—C32	69.0 (2)	B4—N1—O8—B6	−28.9 (1)

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