The first report of the crystal structure of non-solvated μ-oxo boron subphthalocyanine and the crystal structures of two solvated forms

Fulford, M.V.; Lough, A.J.; Bender, T.P.

doi:10.1107/S0108768112037184

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The first report of the crystal structure of non-solvated μ-oxo boron subphthalocyanine and the crystal structures of two solvated forms

M. V. Fulford, A. J. Lough and T. P. Bender

The first instance of the solvent-free X-ray determined single-crystal structure of the oxygen-bridged boron subphthalocyanine dimer [μ-oxo-(BsubPc)₂, C₄₈H₂₄B₂N₁₂O] is reported. Single crystals obtained by train sublimation were found to have μ-oxo-(BsubPc)₂ organized into a C2/c space group. The crystal structure obtained by sublimation is of particular interest as it is highly symmetric and also of notably high density when compared with other BsubPc crystals. The acquisition of this crystal structure came about from the direct chemical synthesis of μ-oxo-(BsubPc)₂ followed by a work-up which culminated in obtaining the single crystals by sublimation. Several methods for the direct chemical synthesis of μ-oxo-(BsubPc)₂ were also investigated each using dichlorobenzene as the solvent. On standing, these reaction mixtures produced a crystal of the dichlorobenzene (DCB) solvate of μ-oxo-(BsubPc)₂ [μ-oxo-(BsubPc)₂·2DCB]. It is also reported that the conversion of bromo-boron subphthalocyanine (Br-BsubPc) to μ-oxo-(BsubPc)₂ happens on train sublimation which resulted in the acquisition of a partially hydrated crystal [μ-oxo-(BsubPc)₂·0.25H₂O].

Keywords: boron subphthalocyanine; oxygen-bridged dimer; solid-state arrangement.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768112037184/ry5043sup1.cif Contains datablocks H2O-m-oxo-BsubPc, DCB-m-oxo-BsubPc, m-oxo-BsubPc-subl, global
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768112037184/ry5043H2O-m-oxo-BsubPcsup2.hkl Contains datablock k11136
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768112037184/ry5043DCB-m-oxo-BsubPcsup3.hkl Contains datablock k11296
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768112037184/ry5043m-oxo-BsubPc-sublsup4.hkl Contains datablock k11292
	Portable Document Format (PDF) file https://doi.org/10.1107/S0108768112037184/ry5043sup5.pdf A full list of general methods and materials, and extra figures and tables

CCDC references: 914861; 914862; 914863

Computing details top

For all compounds, data collection: Collect (Nonius B.V., 1997-2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL V6.1 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL V6.1.

Figures top

(H2O-m-oxo-BsubPc) top

Crystal data top

C₄₈H₂₄B₂N₁₂O·0.25(H₂O)	Z = 2
M_r = 810.92	F(000) = 833
Triclinic, P1	D_x = 1.418 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.4180 (3) Å	Cell parameters from 35416 reflections
b = 13.4413 (6) Å	θ = 2.5–27.4°
c = 13.9207 (6) Å	µ = 0.09 mm⁻¹
α = 87.5640 (19)°	T = 150 K
β = 77.298 (2)°	Block, purple
γ = 88.101 (3)°	0.30 × 0.25 × 0.20 mm
V = 1899.35 (13) Å³

Data collection top

Nonius KappaCCD diffractometer	8597 independent reflections
Radiation source: fine-focus sealed tube	3742 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.113
Detector resolution: 9 pixels mm^-1	θ_max = 27.4°, θ_min = 2.5°
ϕ scans and ω scans with κ offsets	h = −13→13
Absorption correction: multi-scan multi-scan from symmetry-related measurements SORTAV (Blessing 1995)	k = −17→17
T_min = 0.561, T_max = 0.653	l = −17→17
35416 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.067	H-atom parameters constrained
wR(F²) = 0.214	w = 1/[σ²(F_o²) + (0.1108P)²] where P = (F_o² + 2F_c²)/3
S = 0.96	(Δ/σ)_max < 0.001
8597 reflections	Δρ_max = 0.29 e Å⁻³
578 parameters	Δρ_min = −0.29 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0094 (17)

Crystal data top

C₄₈H₂₄B₂N₁₂O·0.25(H₂O)	γ = 88.101 (3)°
M_r = 810.92	V = 1899.35 (13) Å³
Triclinic, P1	Z = 2
a = 10.4180 (3) Å	Mo Kα radiation
b = 13.4413 (6) Å	µ = 0.09 mm⁻¹
c = 13.9207 (6) Å	T = 150 K
α = 87.5640 (19)°	0.30 × 0.25 × 0.20 mm
β = 77.298 (2)°

Data collection top

Nonius KappaCCD diffractometer	8597 independent reflections
Absorption correction: multi-scan multi-scan from symmetry-related measurements SORTAV (Blessing 1995)	3742 reflections with I > 2σ(I)
T_min = 0.561, T_max = 0.653	R_int = 0.113
35416 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.214	H-atom parameters constrained
S = 0.96	Δρ_max = 0.29 e Å⁻³
8597 reflections	Δρ_min = −0.29 e Å⁻³
578 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.25047 (19)	0.18692 (16)	0.15564 (15)	0.0365 (6)
N1	0.2186 (3)	0.3734 (2)	0.3641 (2)	0.0394 (7)
N2	0.3811 (2)	0.29257 (19)	0.24216 (19)	0.0340 (7)
N3	0.5806 (2)	0.2940 (2)	0.1180 (2)	0.0393 (7)
N4	0.3744 (2)	0.32695 (19)	0.07612 (19)	0.0338 (7)
N5	0.2024 (2)	0.4298 (2)	0.03753 (19)	0.0364 (7)
N6	0.1878 (2)	0.36129 (19)	0.20097 (19)	0.0332 (6)
N7	0.3032 (2)	0.08310 (19)	0.40577 (19)	0.0338 (7)
N8	0.3290 (2)	0.03649 (19)	0.23864 (18)	0.0321 (6)
N9	0.3133 (3)	−0.0833 (2)	0.11972 (19)	0.0384 (7)
N10	0.1380 (2)	0.03086 (19)	0.17483 (19)	0.0348 (7)
N11	−0.0688 (2)	0.0804 (2)	0.2745 (2)	0.0380 (7)
N12	0.1325 (2)	0.11730 (18)	0.31927 (19)	0.0321 (6)
C1	0.3382 (3)	0.3292 (2)	0.3342 (2)	0.0353 (8)
C2	0.4539 (3)	0.3335 (2)	0.3758 (2)	0.0388 (8)
C3	0.4716 (4)	0.3671 (3)	0.4654 (3)	0.0464 (9)
H3A	0.3983	0.3851	0.5159	0.056*
C4	0.5991 (4)	0.3735 (3)	0.4789 (3)	0.0521 (10)
H4A	0.6127	0.3943	0.5402	0.063*
C5	0.7071 (4)	0.3501 (3)	0.4047 (3)	0.0532 (10)
H5A	0.7932	0.3565	0.4158	0.064*
C6	0.6923 (4)	0.3174 (3)	0.3144 (3)	0.0475 (9)
H6A	0.7666	0.3016	0.2638	0.057*
C7	0.5643 (3)	0.3089 (2)	0.3008 (2)	0.0375 (8)
C8	0.5161 (3)	0.2900 (2)	0.2132 (2)	0.0351 (8)
C9	0.5088 (3)	0.3178 (2)	0.0514 (2)	0.0349 (8)
C10	0.5459 (3)	0.3592 (2)	−0.0494 (2)	0.0346 (8)
C11	0.6655 (3)	0.3613 (3)	−0.1181 (3)	0.0425 (9)
H11A	0.7442	0.3346	−0.1023	0.051*
C12	0.6649 (4)	0.4041 (3)	−0.2105 (3)	0.0478 (10)
H12A	0.7441	0.4034	−0.2598	0.057*
C13	0.5522 (4)	0.4479 (3)	−0.2329 (3)	0.0456 (9)
H13A	0.5565	0.4773	−0.2968	0.055*
C14	0.4342 (3)	0.4499 (2)	−0.1650 (2)	0.0410 (9)
H14A	0.3584	0.4825	−0.1800	0.049*
C15	0.4299 (3)	0.4024 (2)	−0.0732 (2)	0.0354 (8)
C16	0.3217 (3)	0.3854 (2)	0.0119 (2)	0.0338 (8)
C17	0.1422 (3)	0.4220 (2)	0.1338 (2)	0.0347 (8)
C18	0.0466 (3)	0.4903 (3)	0.1902 (2)	0.0399 (9)
C19	−0.0246 (3)	0.5710 (3)	0.1599 (3)	0.0470 (9)
H19A	−0.0256	0.5832	0.0923	0.056*
C20	−0.0935 (3)	0.6324 (3)	0.2310 (3)	0.0524 (10)
H20A	−0.1413	0.6884	0.2119	0.063*
C21	−0.0945 (3)	0.6141 (3)	0.3306 (3)	0.0531 (10)
H21A	−0.1450	0.6567	0.3782	0.064*
C22	−0.0231 (3)	0.5349 (3)	0.3611 (3)	0.0449 (9)
H22A	−0.0232	0.5235	0.4290	0.054*
C23	0.0488 (3)	0.4724 (3)	0.2907 (2)	0.0387 (8)
C24	0.1479 (3)	0.3945 (2)	0.2946 (2)	0.0364 (8)
C25	0.3719 (3)	0.0373 (2)	0.3249 (2)	0.0333 (8)
C26	0.4723 (3)	−0.0409 (2)	0.3189 (2)	0.0321 (8)
C27	0.5459 (3)	−0.0789 (3)	0.3858 (3)	0.0408 (9)
H27A	0.5514	−0.0424	0.4417	0.049*
C28	0.6097 (3)	−0.1690 (3)	0.3695 (3)	0.0432 (9)
H28A	0.6586	−0.1956	0.4152	0.052*
C29	0.6041 (3)	−0.2224 (3)	0.2871 (3)	0.0446 (9)
H29A	0.6476	−0.2857	0.2785	0.054*
C30	0.5368 (3)	−0.1854 (3)	0.2175 (3)	0.0403 (9)
H30A	0.5353	−0.2215	0.1606	0.048*
C31	0.4715 (3)	−0.0940 (2)	0.2335 (2)	0.0341 (8)
C32	0.3750 (3)	−0.0453 (2)	0.1854 (2)	0.0357 (8)
C33	0.1929 (3)	−0.0469 (2)	0.1190 (2)	0.0346 (8)
C34	0.0845 (3)	−0.0903 (2)	0.0857 (2)	0.0348 (8)
C35	0.0808 (3)	−0.1666 (3)	0.0214 (2)	0.0421 (9)
H35A	0.1593	−0.2003	−0.0103	0.050*
C36	−0.0398 (4)	−0.1919 (3)	0.0050 (3)	0.0467 (9)
H36A	−0.0440	−0.2424	−0.0398	0.056*
C37	−0.1559 (4)	−0.1442 (3)	0.0534 (3)	0.0477 (10)
H37A	−0.2374	−0.1628	0.0405	0.057*
C38	−0.1548 (3)	−0.0703 (3)	0.1198 (2)	0.0434 (9)
H38A	−0.2345	−0.0403	0.1544	0.052*
C39	−0.0336 (3)	−0.0416 (2)	0.1341 (2)	0.0383 (8)
C40	0.0032 (3)	0.0325 (2)	0.1966 (2)	0.0352 (8)
C41	−0.0022 (3)	0.1150 (2)	0.3383 (2)	0.0348 (8)
C42	−0.0473 (3)	0.1339 (2)	0.4429 (2)	0.0333 (8)
C43	−0.1719 (3)	0.1469 (2)	0.5021 (3)	0.0413 (9)
H43A	−0.2483	0.1446	0.4755	0.050*
C44	−0.1817 (3)	0.1632 (3)	0.6002 (3)	0.0430 (9)
H44A	−0.2658	0.1771	0.6408	0.052*
C45	−0.0707 (3)	0.1596 (2)	0.6418 (3)	0.0411 (9)
H45A	−0.0810	0.1691	0.7104	0.049*
C46	0.0534 (3)	0.1425 (2)	0.5844 (2)	0.0377 (8)
H46A	0.1281	0.1372	0.6131	0.045*
C47	0.0667 (3)	0.1331 (2)	0.4839 (2)	0.0323 (8)
C48	0.1809 (3)	0.1151 (2)	0.4037 (2)	0.0307 (7)
B1	0.2937 (4)	0.2822 (3)	0.1702 (3)	0.0326 (9)
B2	0.2161 (3)	0.1016 (3)	0.2183 (3)	0.0344 (9)
O1W	0.8426 (12)	0.3825 (10)	0.0814 (9)	0.085 (4)	0.25
H1WA	0.8307	0.4345	0.0484	0.128*	0.25
H1WB	0.7681	0.3570	0.0919	0.128*	0.25

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0491 (13)	0.0311 (13)	0.0321 (13)	−0.0106 (10)	−0.0140 (10)	0.0012 (10)
N1	0.0498 (18)	0.0325 (17)	0.0364 (17)	−0.0051 (13)	−0.0107 (14)	0.0014 (13)
N2	0.0437 (16)	0.0292 (16)	0.0322 (16)	−0.0079 (12)	−0.0139 (12)	−0.0008 (12)
N3	0.0428 (16)	0.0351 (17)	0.0430 (18)	−0.0025 (13)	−0.0163 (14)	0.0011 (14)
N4	0.0401 (16)	0.0300 (16)	0.0332 (15)	−0.0019 (12)	−0.0126 (12)	0.0025 (12)
N5	0.0423 (16)	0.0331 (16)	0.0367 (17)	0.0024 (13)	−0.0148 (13)	−0.0053 (13)
N6	0.0415 (15)	0.0275 (15)	0.0313 (15)	−0.0048 (12)	−0.0092 (12)	0.0004 (13)
N7	0.0343 (15)	0.0305 (16)	0.0384 (16)	−0.0022 (12)	−0.0107 (12)	−0.0068 (13)
N8	0.0361 (14)	0.0318 (16)	0.0306 (15)	−0.0048 (12)	−0.0113 (12)	−0.0035 (13)
N9	0.0438 (16)	0.0373 (17)	0.0357 (16)	−0.0051 (13)	−0.0108 (13)	−0.0069 (13)
N10	0.0411 (16)	0.0315 (16)	0.0348 (16)	−0.0060 (12)	−0.0139 (12)	−0.0003 (13)
N11	0.0406 (16)	0.0333 (17)	0.0433 (17)	−0.0034 (13)	−0.0168 (14)	0.0026 (14)
N12	0.0384 (16)	0.0264 (15)	0.0347 (16)	−0.0018 (11)	−0.0148 (12)	0.0017 (12)
C1	0.053 (2)	0.0245 (18)	0.0316 (19)	−0.0075 (15)	−0.0156 (16)	0.0018 (15)
C2	0.052 (2)	0.029 (2)	0.041 (2)	−0.0042 (15)	−0.0211 (17)	0.0010 (16)
C3	0.064 (2)	0.037 (2)	0.042 (2)	−0.0034 (18)	−0.0209 (18)	0.0008 (17)
C4	0.070 (3)	0.047 (2)	0.047 (2)	−0.006 (2)	−0.030 (2)	0.0002 (19)
C5	0.063 (3)	0.042 (2)	0.067 (3)	−0.0101 (19)	−0.040 (2)	0.002 (2)
C6	0.057 (2)	0.035 (2)	0.056 (2)	−0.0041 (17)	−0.0241 (19)	0.0015 (18)
C7	0.047 (2)	0.0277 (19)	0.043 (2)	−0.0039 (15)	−0.0206 (17)	0.0025 (16)
C8	0.043 (2)	0.0273 (19)	0.037 (2)	−0.0004 (15)	−0.0132 (16)	−0.0012 (15)
C9	0.040 (2)	0.0287 (19)	0.037 (2)	−0.0037 (14)	−0.0103 (15)	−0.0039 (15)
C10	0.0421 (19)	0.0271 (19)	0.0357 (19)	−0.0080 (15)	−0.0092 (15)	−0.0046 (15)
C11	0.048 (2)	0.036 (2)	0.043 (2)	−0.0127 (16)	−0.0060 (17)	−0.0053 (17)
C12	0.059 (2)	0.038 (2)	0.042 (2)	−0.0188 (18)	0.0039 (18)	−0.0017 (18)
C13	0.066 (2)	0.035 (2)	0.034 (2)	−0.0125 (18)	−0.0075 (18)	0.0007 (16)
C14	0.062 (2)	0.0270 (19)	0.034 (2)	−0.0079 (16)	−0.0111 (17)	0.0001 (15)
C15	0.045 (2)	0.0288 (19)	0.0342 (19)	−0.0062 (15)	−0.0112 (15)	−0.0035 (15)
C16	0.044 (2)	0.0248 (18)	0.0367 (19)	0.0007 (15)	−0.0182 (16)	−0.0035 (15)
C17	0.0378 (18)	0.036 (2)	0.0328 (19)	−0.0087 (15)	−0.0110 (15)	−0.0026 (16)
C18	0.0360 (19)	0.043 (2)	0.041 (2)	−0.0014 (16)	−0.0101 (16)	−0.0022 (17)
C19	0.041 (2)	0.053 (3)	0.048 (2)	0.0003 (18)	−0.0122 (17)	0.0014 (19)
C20	0.043 (2)	0.053 (3)	0.056 (3)	0.0069 (18)	−0.0035 (18)	0.000 (2)
C21	0.047 (2)	0.048 (3)	0.059 (3)	0.0010 (18)	−0.0002 (19)	−0.007 (2)
C22	0.051 (2)	0.043 (2)	0.040 (2)	−0.0045 (18)	−0.0075 (17)	−0.0023 (18)
C23	0.0361 (18)	0.039 (2)	0.039 (2)	−0.0049 (15)	−0.0040 (15)	0.0015 (17)
C24	0.0428 (19)	0.033 (2)	0.034 (2)	−0.0091 (15)	−0.0079 (15)	−0.0001 (16)
C25	0.0357 (18)	0.0306 (19)	0.0362 (19)	−0.0057 (14)	−0.0121 (15)	−0.0037 (15)
C26	0.0341 (17)	0.0301 (19)	0.0339 (19)	−0.0020 (14)	−0.0104 (14)	−0.0035 (15)
C27	0.0402 (19)	0.039 (2)	0.045 (2)	0.0024 (16)	−0.0145 (16)	−0.0078 (17)
C28	0.0401 (19)	0.040 (2)	0.054 (2)	−0.0016 (16)	−0.0189 (17)	−0.0005 (19)
C29	0.0356 (19)	0.037 (2)	0.062 (3)	0.0013 (15)	−0.0127 (17)	−0.0087 (19)
C30	0.0369 (18)	0.035 (2)	0.049 (2)	−0.0038 (15)	−0.0063 (16)	−0.0141 (17)
C31	0.0284 (17)	0.0307 (19)	0.043 (2)	−0.0029 (14)	−0.0069 (14)	−0.0054 (16)
C32	0.0417 (19)	0.033 (2)	0.0320 (18)	−0.0074 (15)	−0.0058 (15)	−0.0054 (16)
C33	0.047 (2)	0.0275 (19)	0.0313 (19)	−0.0072 (15)	−0.0109 (15)	−0.0022 (15)
C34	0.050 (2)	0.0272 (19)	0.0313 (18)	−0.0096 (15)	−0.0173 (15)	0.0022 (15)
C35	0.058 (2)	0.038 (2)	0.034 (2)	−0.0135 (17)	−0.0183 (16)	0.0035 (17)
C36	0.066 (3)	0.038 (2)	0.043 (2)	−0.0206 (19)	−0.0257 (19)	0.0082 (17)
C37	0.059 (2)	0.050 (2)	0.042 (2)	−0.0255 (19)	−0.0276 (19)	0.0108 (19)
C38	0.054 (2)	0.043 (2)	0.039 (2)	−0.0164 (17)	−0.0231 (17)	0.0118 (18)
C39	0.046 (2)	0.032 (2)	0.042 (2)	−0.0087 (16)	−0.0197 (16)	0.0041 (16)
C40	0.0385 (19)	0.0274 (19)	0.041 (2)	−0.0041 (14)	−0.0127 (15)	0.0051 (16)
C41	0.0369 (19)	0.0299 (19)	0.041 (2)	−0.0036 (14)	−0.0157 (15)	0.0029 (16)
C42	0.0388 (19)	0.0247 (18)	0.038 (2)	−0.0030 (14)	−0.0119 (15)	0.0024 (15)
C43	0.038 (2)	0.037 (2)	0.047 (2)	−0.0016 (15)	−0.0075 (16)	0.0001 (17)
C44	0.040 (2)	0.038 (2)	0.047 (2)	−0.0035 (16)	−0.0016 (17)	0.0006 (17)
C45	0.050 (2)	0.035 (2)	0.038 (2)	−0.0075 (16)	−0.0074 (17)	0.0011 (16)
C46	0.0418 (19)	0.032 (2)	0.040 (2)	−0.0037 (15)	−0.0085 (16)	0.0010 (16)
C47	0.0364 (18)	0.0250 (18)	0.0359 (19)	−0.0015 (14)	−0.0090 (15)	−0.0007 (14)
C48	0.0394 (19)	0.0245 (18)	0.0306 (18)	−0.0047 (14)	−0.0117 (14)	−0.0021 (14)
B1	0.045 (2)	0.025 (2)	0.030 (2)	−0.0047 (17)	−0.0120 (17)	0.0010 (16)
B2	0.040 (2)	0.031 (2)	0.034 (2)	−0.0031 (17)	−0.0123 (17)	−0.0023 (18)
O1W	0.103 (9)	0.086 (10)	0.070 (8)	0.004 (7)	−0.026 (7)	0.000 (7)

Geometric parameters (Å, º) top

O1—B1	1.409 (4)	C14—C15	1.396 (4)
O1—B2	1.417 (4)	C14—H14A	0.9500
N1—C1	1.350 (4)	C15—C16	1.460 (4)
N1—C24	1.355 (4)	C17—C18	1.452 (4)
N2—C1	1.369 (4)	C18—C19	1.397 (5)
N2—C8	1.375 (4)	C18—C23	1.415 (5)
N2—B1	1.508 (4)	C19—C20	1.376 (5)
N3—C9	1.337 (4)	C19—H19A	0.9500
N3—C8	1.347 (4)	C20—C21	1.395 (5)
N4—C16	1.359 (4)	C20—H20A	0.9500
N4—C9	1.369 (4)	C21—C22	1.384 (5)
N4—B1	1.506 (4)	C21—H21A	0.9500
N5—C16	1.343 (4)	C22—C23	1.391 (5)
N5—C17	1.350 (4)	C22—H22A	0.9500
N6—C24	1.367 (4)	C23—C24	1.454 (5)
N6—C17	1.368 (4)	C25—C26	1.450 (4)
N6—B1	1.511 (4)	C26—C27	1.402 (4)
N7—C48	1.338 (4)	C26—C31	1.414 (4)
N7—C25	1.353 (4)	C27—C28	1.365 (5)
N8—C32	1.366 (4)	C27—H27A	0.9500
N8—C25	1.371 (4)	C28—C29	1.392 (5)
N8—B2	1.513 (4)	C28—H28A	0.9500
N9—C33	1.333 (4)	C29—C30	1.383 (5)
N9—C32	1.352 (4)	C29—H29A	0.9500
N10—C33	1.364 (4)	C30—C31	1.387 (4)
N10—C40	1.370 (4)	C30—H30A	0.9500
N10—B2	1.500 (4)	C31—C32	1.450 (4)
N11—C41	1.346 (4)	C33—C34	1.458 (4)
N11—C40	1.351 (4)	C34—C35	1.396 (5)
N12—C41	1.371 (4)	C34—C39	1.420 (4)
N12—C48	1.375 (4)	C35—C36	1.381 (4)
N12—B2	1.501 (4)	C35—H35A	0.9500
C1—C2	1.452 (4)	C36—C37	1.398 (5)
C2—C3	1.396 (5)	C36—H36A	0.9500
C2—C7	1.413 (4)	C37—C38	1.386 (5)
C3—C4	1.387 (5)	C37—H37A	0.9500
C3—H3A	0.9500	C38—C39	1.390 (4)
C4—C5	1.388 (5)	C38—H38A	0.9500
C4—H4A	0.9500	C39—C40	1.463 (5)
C5—C6	1.390 (5)	C41—C42	1.458 (4)
C5—H5A	0.9500	C42—C43	1.386 (4)
C6—C7	1.397 (4)	C42—C47	1.426 (4)
C6—H6A	0.9500	C43—C44	1.374 (5)
C7—C8	1.453 (4)	C43—H43A	0.9500
C9—C10	1.461 (4)	C44—C45	1.401 (5)
C10—C11	1.395 (4)	C44—H44A	0.9500
C10—C15	1.421 (4)	C45—C46	1.380 (4)
C11—C12	1.387 (5)	C45—H45A	0.9500
C11—H11A	0.9500	C46—C47	1.386 (4)
C12—C13	1.387 (5)	C46—H46A	0.9500
C12—H12A	0.9500	C47—C48	1.462 (4)
C13—C14	1.377 (5)	O1W—H1WA	0.8401
C13—H13A	0.9500	O1W—H1WB	0.8399

B1—O1—B2	133.6 (3)	C22—C23—C18	119.6 (3)
C1—N1—C24	117.1 (3)	C22—C23—C24	132.8 (3)
C1—N2—C8	112.3 (3)	C18—C23—C24	106.9 (3)
C1—N2—B1	123.7 (3)	N1—C24—N6	121.6 (3)
C8—N2—B1	122.1 (3)	N1—C24—C23	129.7 (3)
C9—N3—C8	116.8 (3)	N6—C24—C23	106.4 (3)
C16—N4—C9	114.1 (3)	N7—C25—N8	122.7 (3)
C16—N4—B1	123.1 (3)	N7—C25—C26	128.6 (3)
C9—N4—B1	122.6 (3)	N8—C25—C26	106.1 (3)
C16—N5—C17	116.4 (3)	C27—C26—C31	119.4 (3)
C24—N6—C17	112.0 (3)	C27—C26—C25	132.6 (3)
C24—N6—B1	124.5 (3)	C31—C26—C25	107.0 (3)
C17—N6—B1	122.1 (3)	C28—C27—C26	119.1 (3)
C48—N7—C25	116.8 (3)	C28—C27—H27A	120.5
C32—N8—C25	112.2 (3)	C26—C27—H27A	120.5
C32—N8—B2	122.5 (3)	C27—C28—C29	121.0 (3)
C25—N8—B2	123.3 (3)	C27—C28—H28A	119.5
C33—N9—C32	116.8 (3)	C29—C28—H28A	119.5
C33—N10—C40	113.6 (3)	C30—C29—C28	121.5 (3)
C33—N10—B2	123.6 (3)	C30—C29—H29A	119.2
C40—N10—B2	122.4 (3)	C28—C29—H29A	119.2
C41—N11—C40	116.5 (3)	C29—C30—C31	117.9 (3)
C41—N12—C48	112.7 (3)	C29—C30—H30A	121.1
C41—N12—B2	122.1 (3)	C31—C30—H30A	121.1
C48—N12—B2	123.9 (3)	C30—C31—C26	121.0 (3)
N1—C1—N2	122.9 (3)	C30—C31—C32	130.5 (3)
N1—C1—C2	129.2 (3)	C26—C31—C32	107.4 (3)
N2—C1—C2	106.0 (3)	N9—C32—N8	123.3 (3)
C3—C2—C7	120.1 (3)	N9—C32—C31	128.2 (3)
C3—C2—C1	132.1 (3)	N8—C32—C31	106.2 (3)
C7—C2—C1	107.3 (3)	N9—C33—N10	122.3 (3)
C4—C3—C2	118.3 (3)	N9—C33—C34	130.6 (3)
C4—C3—H3A	120.9	N10—C33—C34	105.3 (3)
C2—C3—H3A	120.9	C35—C34—C39	120.4 (3)
C3—C4—C5	121.4 (4)	C35—C34—C33	132.0 (3)
C3—C4—H4A	119.3	C39—C34—C33	107.5 (3)
C5—C4—H4A	119.3	C36—C35—C34	118.4 (3)
C4—C5—C6	121.5 (3)	C36—C35—H35A	120.8
C4—C5—H5A	119.3	C34—C35—H35A	120.8
C6—C5—H5A	119.3	C35—C36—C37	120.9 (4)
C5—C6—C7	117.6 (3)	C35—C36—H36A	119.5
C5—C6—H6A	121.2	C37—C36—H36A	119.5
C7—C6—H6A	121.2	C38—C37—C36	121.6 (3)
C6—C7—C2	121.2 (3)	C38—C37—H37A	119.2
C6—C7—C8	130.9 (3)	C36—C37—H37A	119.2
C2—C7—C8	107.4 (3)	C37—C38—C39	117.9 (3)
N3—C8—N2	123.1 (3)	C37—C38—H38A	121.0
N3—C8—C7	129.2 (3)	C39—C38—H38A	121.0
N2—C8—C7	105.7 (3)	C38—C39—C34	120.6 (3)
N3—C9—N4	122.3 (3)	C38—C39—C40	132.3 (3)
N3—C9—C10	131.4 (3)	C34—C39—C40	107.0 (3)
N4—C9—C10	105.0 (3)	N11—C40—N10	122.3 (3)
C11—C10—C15	120.6 (3)	N11—C40—C39	131.1 (3)
C11—C10—C9	132.3 (3)	N10—C40—C39	105.3 (3)
C15—C10—C9	107.1 (3)	N11—C41—N12	123.0 (3)
C12—C11—C10	117.3 (3)	N11—C41—C42	129.6 (3)
C12—C11—H11A	121.4	N12—C41—C42	106.0 (3)
C10—C11—H11A	121.4	C43—C42—C47	120.7 (3)
C13—C12—C11	121.9 (3)	C43—C42—C41	132.2 (3)
C13—C12—H12A	119.0	C47—C42—C41	107.0 (3)
C11—C12—H12A	119.0	C44—C43—C42	118.1 (3)
C14—C13—C12	121.6 (3)	C44—C43—H43A	121.0
C14—C13—H13A	119.2	C42—C43—H43A	121.0
C12—C13—H13A	119.2	C43—C44—C45	121.6 (3)
C13—C14—C15	117.8 (3)	C43—C44—H44A	119.2
C13—C14—H14A	121.1	C45—C44—H44A	119.2
C15—C14—H14A	121.1	C46—C45—C44	120.7 (3)
C14—C15—C10	120.6 (3)	C46—C45—H45A	119.6
C14—C15—C16	131.9 (3)	C44—C45—H45A	119.6
C10—C15—C16	107.5 (3)	C45—C46—C47	118.7 (3)
N5—C16—N4	122.5 (3)	C45—C46—H46A	120.7
N5—C16—C15	131.1 (3)	C47—C46—H46A	120.7
N4—C16—C15	105.1 (3)	C46—C47—C42	120.0 (3)
N5—C17—N6	123.4 (3)	C46—C47—C48	132.6 (3)
N5—C17—C18	128.2 (3)	C42—C47—C48	107.3 (3)
N6—C17—C18	106.4 (3)	N7—C48—N12	122.6 (3)
C19—C18—C23	121.2 (3)	N7—C48—C47	130.7 (3)
C19—C18—C17	130.9 (3)	N12—C48—C47	105.5 (3)
C23—C18—C17	107.2 (3)	O1—B1—N4	111.3 (3)
C20—C19—C18	117.9 (3)	O1—B1—N2	118.9 (3)
C20—C19—H19A	121.1	N4—B1—N2	102.7 (3)
C18—C19—H19A	121.1	O1—B1—N6	116.4 (3)
C19—C20—C21	121.4 (4)	N4—B1—N6	102.5 (3)
C19—C20—H20A	119.3	N2—B1—N6	103.0 (3)
C21—C20—H20A	119.3	O1—B2—N10	111.6 (3)
C22—C21—C20	121.1 (3)	O1—B2—N12	117.7 (3)
C22—C21—H21A	119.5	N10—B2—N12	103.3 (2)
C20—C21—H21A	119.5	O1—B2—N8	116.4 (3)
C21—C22—C23	118.8 (3)	N10—B2—N8	102.9 (3)
C21—C22—H22A	120.6	N12—B2—N8	103.1 (3)
C23—C22—H22A	120.6	H1WA—O1W—H1WB	101.6

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···N5ⁱ	0.84	2.20	3.038 (13)	180
O1W—H1WB···N3	0.84	2.11	2.946 (13)	180

Symmetry code: (i) −x+1, −y+1, −z.

(DCB-m-oxo-BsubPc) top

Crystal data top

C₄₈H₂₄B₂N₁₂O·2(C₆H₄Cl₂)	Z = 2
M_r = 1100.40	F(000) = 1124
Triclinic, P1	D_x = 1.438 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.3894 (3) Å	Cell parameters from 25833 reflections
b = 13.2623 (3) Å	θ = 2.6–27.5°
c = 17.6618 (6) Å	µ = 0.29 mm⁻¹
α = 78.3470 (16)°	T = 150 K
β = 85.6160 (13)°	Plate, purple
γ = 76.7400 (17)°	0.34 × 0.16 × 0.08 mm
V = 2541.89 (12) Å³

Data collection top

Nonius KappaCCD diffractometer	11383 independent reflections
Radiation source: fine-focus sealed tube	6168 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.076
Detector resolution: 9 pixels mm^-1	θ_max = 27.5°, θ_min = 2.6°
ϕ scans and ω scans with κ offsets	h = −14→14
Absorption correction: multi-scan multi-scan from symmetry-related measurements SORTAV (Blessing 1995)	k = −17→17
T_min = 0.808, T_max = 0.985	l = −22→22
26858 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.085	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.217	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.075P)² + 4.0961P] where P = (F_o² + 2F_c²)/3
11383 reflections	(Δ/σ)_max = 0.001
738 parameters	Δρ_max = 0.83 e Å⁻³
48 restraints	Δρ_min = −0.50 e Å⁻³

Crystal data top

C₄₈H₂₄B₂N₁₂O·2(C₆H₄Cl₂)	γ = 76.7400 (17)°
M_r = 1100.40	V = 2541.89 (12) Å³
Triclinic, P1	Z = 2
a = 11.3894 (3) Å	Mo Kα radiation
b = 13.2623 (3) Å	µ = 0.29 mm⁻¹
c = 17.6618 (6) Å	T = 150 K
α = 78.3470 (16)°	0.34 × 0.16 × 0.08 mm
β = 85.6160 (13)°

Data collection top

Nonius KappaCCD diffractometer	11383 independent reflections
Absorption correction: multi-scan multi-scan from symmetry-related measurements SORTAV (Blessing 1995)	6168 reflections with I > 2σ(I)
T_min = 0.808, T_max = 0.985	R_int = 0.076
26858 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.085	48 restraints
wR(F²) = 0.217	H-atom parameters constrained
S = 1.01	Δρ_max = 0.83 e Å⁻³
11383 reflections	Δρ_min = −0.50 e Å⁻³
738 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.0697 (2)	0.14528 (18)	0.70448 (14)	0.0273 (6)
N1	−0.1088 (3)	0.2948 (2)	0.53428 (17)	0.0281 (7)
N2	0.0302 (3)	0.3218 (2)	0.61763 (17)	0.0252 (7)
N3	0.1918 (3)	0.3927 (2)	0.64436 (17)	0.0302 (7)
N4	0.2281 (3)	0.2171 (2)	0.62092 (17)	0.0257 (7)
N5	0.2802 (3)	0.0915 (2)	0.53803 (17)	0.0284 (7)
N6	0.0753 (3)	0.1684 (2)	0.56357 (16)	0.0237 (6)
N7	−0.1375 (3)	0.3814 (2)	0.78021 (17)	0.0291 (7)
N8	0.0477 (3)	0.2556 (2)	0.80639 (17)	0.0277 (7)
N9	0.1877 (3)	0.1359 (2)	0.89439 (18)	0.0294 (7)
N10	0.0391 (3)	0.0765 (2)	0.83945 (17)	0.0254 (7)
N11	−0.1473 (3)	0.0281 (2)	0.83751 (17)	0.0276 (7)
N12	−0.1231 (3)	0.2004 (2)	0.77720 (17)	0.0264 (7)
C1	−0.0737 (3)	0.3547 (3)	0.5782 (2)	0.0265 (8)
C2	−0.1156 (3)	0.4657 (3)	0.5809 (2)	0.0300 (9)
C3	−0.2203 (4)	0.5388 (3)	0.5565 (2)	0.0363 (9)
H3A	−0.2800	0.5201	0.5307	0.044*
C4	−0.2349 (4)	0.6392 (3)	0.5710 (2)	0.0417 (10)
H4A	−0.3071	0.6898	0.5564	0.050*
C5	−0.1460 (4)	0.6684 (3)	0.6066 (2)	0.0406 (10)
H5A	−0.1596	0.7380	0.6165	0.049*
C6	−0.0386 (4)	0.5981 (3)	0.6276 (2)	0.0385 (10)
H6A	0.0233	0.6196	0.6493	0.046*
C7	−0.0236 (3)	0.4954 (3)	0.6162 (2)	0.0294 (8)
C8	0.0745 (3)	0.4030 (3)	0.6323 (2)	0.0267 (8)
C9	0.2676 (3)	0.3027 (3)	0.6325 (2)	0.0275 (8)
C10	0.3949 (3)	0.2838 (3)	0.6102 (2)	0.0302 (8)
C11	0.4806 (4)	0.3446 (3)	0.6076 (2)	0.0378 (10)
H11A	0.4615	0.4093	0.6259	0.045*
C12	0.5943 (4)	0.3076 (3)	0.5775 (3)	0.0455 (11)
H12A	0.6549	0.3465	0.5767	0.055*
C13	0.6223 (4)	0.2149 (3)	0.5483 (3)	0.0420 (10)
H13A	0.7014	0.1922	0.5278	0.050*
C14	0.5377 (4)	0.1549 (3)	0.5485 (2)	0.0375 (10)
H14A	0.5573	0.0919	0.5281	0.045*
C15	0.4228 (3)	0.1898 (3)	0.5794 (2)	0.0311 (9)
C16	0.3114 (3)	0.1534 (3)	0.5818 (2)	0.0269 (8)
C17	0.1612 (3)	0.1063 (3)	0.5262 (2)	0.0255 (8)
C18	0.1016 (3)	0.0867 (3)	0.4625 (2)	0.0291 (8)
C19	0.1460 (4)	0.0291 (3)	0.4039 (2)	0.0349 (9)
H19A	0.2271	−0.0096	0.4029	0.042*
C20	0.0671 (4)	0.0311 (3)	0.3480 (2)	0.0416 (10)
H20A	0.0935	−0.0099	0.3091	0.050*
C21	−0.0500 (4)	0.0915 (3)	0.3471 (2)	0.0434 (11)
H21A	−0.1013	0.0910	0.3072	0.052*
C22	−0.0944 (4)	0.1523 (3)	0.4022 (2)	0.0366 (10)
H22A	−0.1737	0.1953	0.4000	0.044*
C23	−0.0170 (3)	0.1477 (3)	0.4615 (2)	0.0279 (8)
C24	−0.0294 (3)	0.2061 (3)	0.5243 (2)	0.0268 (8)
C25	−0.0227 (3)	0.3558 (3)	0.8014 (2)	0.0279 (8)
C26	0.0416 (3)	0.4109 (3)	0.8421 (2)	0.0312 (9)
C27	0.0143 (4)	0.5137 (3)	0.8558 (2)	0.0391 (10)
H27A	−0.0527	0.5644	0.8327	0.047*
C28	0.0882 (4)	0.5392 (3)	0.9043 (3)	0.0474 (11)
H28A	0.0720	0.6092	0.9139	0.057*
C29	0.1856 (4)	0.4654 (3)	0.9393 (3)	0.0470 (11)
H29A	0.2342	0.4858	0.9723	0.056*
C30	0.2129 (4)	0.3629 (3)	0.9271 (2)	0.0379 (10)
H30A	0.2789	0.3125	0.9517	0.045*
C31	0.1405 (3)	0.3356 (3)	0.8774 (2)	0.0318 (9)
C32	0.1378 (3)	0.2345 (3)	0.8579 (2)	0.0289 (8)
C33	0.1322 (3)	0.0594 (3)	0.8878 (2)	0.0275 (8)
C34	0.1354 (3)	−0.0447 (3)	0.9358 (2)	0.0280 (8)
C35	0.2140 (4)	−0.1071 (3)	0.9918 (2)	0.0327 (9)
H35A	0.2811	−0.0839	1.0055	0.039*
C36	0.1912 (4)	−0.2044 (3)	1.0272 (2)	0.0371 (10)
H36A	0.2453	−0.2494	1.0643	0.045*
C37	0.0907 (4)	−0.2375 (3)	1.0094 (2)	0.0362 (10)
H37A	0.0783	−0.3049	1.0344	0.043*
C38	0.0081 (4)	−0.1743 (3)	0.9558 (2)	0.0336 (9)
H38A	−0.0622	−0.1958	0.9457	0.040*
C39	0.0324 (3)	−0.0785 (3)	0.9177 (2)	0.0278 (8)
C40	−0.0330 (3)	0.0060 (3)	0.8596 (2)	0.0261 (8)
C41	−0.1936 (3)	0.1278 (3)	0.8021 (2)	0.0283 (8)
C42	−0.3180 (3)	0.1873 (3)	0.7987 (2)	0.0304 (9)
C43	−0.4266 (4)	0.1563 (3)	0.8165 (2)	0.0371 (9)
H43A	−0.4289	0.0836	0.8290	0.045*
C44	−0.5307 (4)	0.2330 (4)	0.8155 (3)	0.0449 (11)
H44A	−0.6060	0.2128	0.8266	0.054*
C45	−0.5282 (4)	0.3408 (4)	0.7982 (2)	0.0429 (10)
H45A	−0.6017	0.3921	0.7982	0.052*
C46	−0.4210 (4)	0.3733 (3)	0.7813 (2)	0.0370 (9)
H46A	−0.4194	0.4461	0.7705	0.044*
C47	−0.3148 (3)	0.2958 (3)	0.7807 (2)	0.0306 (9)
C48	−0.1881 (3)	0.3018 (3)	0.7726 (2)	0.0280 (8)
B1	0.0978 (4)	0.2079 (3)	0.6339 (2)	0.0249 (9)
B2	0.0129 (4)	0.1702 (3)	0.7743 (2)	0.0279 (9)
Cl1	0.56413 (18)	−0.11952 (13)	0.96265 (11)	0.0654 (5)	0.853 (3)
Cl2	0.48293 (16)	−0.33714 (14)	0.98225 (11)	0.0751 (6)	0.853 (3)
C1S	0.6196 (3)	−0.2070 (2)	0.9018 (2)	0.0474 (14)	0.853 (3)
C2S	0.5819 (3)	−0.3012 (3)	0.9095 (2)	0.0512 (14)	0.853 (3)
C3S	0.6268 (3)	−0.3692 (2)	0.8585 (2)	0.0517 (15)	0.853 (3)
H3S	0.6010	−0.4336	0.8637	0.062*	0.853 (3)
C4S	0.7094 (3)	−0.3431 (3)	0.7999 (2)	0.0545 (15)	0.853 (3)
H4S	0.7401	−0.3896	0.7651	0.065*	0.853 (3)
C5S	0.7472 (3)	−0.2489 (3)	0.79230 (19)	0.0587 (16)	0.853 (3)
H5S	0.8036	−0.2311	0.7523	0.070*	0.853 (3)
C6S	0.7023 (3)	−0.1809 (2)	0.8433 (2)	0.0521 (15)	0.853 (3)
H6S	0.7280	−0.1165	0.8380	0.063*	0.853 (3)
Cl1B	0.8119 (17)	−0.2195 (15)	0.7949 (11)	0.150*	0.147 (3)
Cl2B	0.6724 (19)	−0.4007 (14)	0.8314 (13)	0.150*	0.147 (3)
C1B	0.691 (4)	−0.213 (3)	0.860 (3)	0.150*	0.147 (3)
C2B	0.633 (4)	−0.297 (3)	0.879 (3)	0.150*	0.147 (3)
C3B	0.537 (4)	−0.293 (3)	0.932 (3)	0.150*	0.147 (3)
H3B	0.4897	−0.3447	0.9400	0.180*	0.147 (3)
C4B	0.511 (4)	−0.212 (3)	0.975 (2)	0.150*	0.147 (3)
H4B	0.4566	−0.2158	1.0183	0.180*	0.147 (3)
C5B	0.564 (5)	−0.126 (3)	0.952 (3)	0.150*	0.147 (3)
H5B	0.5325	−0.0626	0.9717	0.180*	0.147 (3)
C6B	0.664 (4)	−0.132 (3)	0.902 (3)	0.150*	0.147 (3)
H6B	0.7137	−0.0823	0.8962	0.180*	0.147 (3)
Cl3	0.54357 (17)	0.87526 (14)	0.63271 (11)	0.0643 (6)	0.756 (3)
Cl4	0.3882 (3)	0.9583 (2)	0.77344 (15)	0.1175 (12)	0.756 (3)
C7S	0.4474 (4)	0.8065 (4)	0.6886 (3)	0.0567 (15)	0.756 (3)
C8S	0.3815 (5)	0.8417 (4)	0.7513 (3)	0.086 (2)	0.756 (3)
C9S	0.3048 (5)	0.7829 (5)	0.7950 (3)	0.127 (4)	0.756 (3)
H9S	0.2597	0.8070	0.8379	0.152*	0.756 (3)
C10S	0.2941 (6)	0.6888 (5)	0.7759 (4)	0.165 (5)	0.756 (3)
H10S	0.2418	0.6486	0.8057	0.198*	0.756 (3)
C11S	0.3601 (5)	0.6535 (4)	0.7131 (4)	0.105 (3)	0.756 (3)
H11S	0.3528	0.5892	0.7001	0.126*	0.756 (3)
C12S	0.4368 (5)	0.7124 (4)	0.6695 (3)	0.0711 (18)	0.756 (3)
H12S	0.4819	0.6883	0.6266	0.085*	0.756 (3)
Cl3A	0.4619 (7)	0.6519 (6)	0.6474 (5)	0.100*	0.244 (3)
Cl4A	0.2807 (9)	0.6672 (7)	0.7869 (6)	0.100*	0.244 (3)
C7A	0.428 (3)	0.7624 (16)	0.6879 (16)	0.100*	0.244 (3)
C8A	0.351 (2)	0.7671 (14)	0.7529 (13)	0.100*	0.244 (3)
C9A	0.329 (3)	0.8547 (14)	0.7878 (14)	0.100*	0.244 (3)
H9A	0.2809	0.8563	0.8340	0.120*	0.244 (3)
C10A	0.379 (3)	0.9402 (13)	0.7545 (17)	0.100*	0.244 (3)
H10A	0.3496	1.0071	0.7685	0.120*	0.244 (3)
C11A	0.474 (2)	0.9261 (13)	0.7002 (13)	0.100*	0.244 (3)
H11B	0.5235	0.9764	0.6871	0.120*	0.244 (3)
C12A	0.496 (2)	0.8382 (16)	0.6651 (15)	0.100*	0.244 (3)
H12B	0.5578	0.8302	0.6259	0.120*	0.244 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0287 (14)	0.0285 (13)	0.0252 (14)	−0.0085 (11)	0.0055 (11)	−0.0060 (11)
N1	0.0220 (16)	0.0341 (17)	0.0281 (17)	−0.0083 (14)	0.0026 (13)	−0.0042 (14)
N2	0.0230 (17)	0.0257 (16)	0.0283 (17)	−0.0076 (13)	0.0040 (13)	−0.0076 (13)
N3	0.0318 (19)	0.0330 (17)	0.0280 (17)	−0.0114 (14)	0.0047 (14)	−0.0083 (14)
N4	0.0249 (16)	0.0264 (16)	0.0266 (17)	−0.0070 (13)	−0.0003 (13)	−0.0052 (13)
N5	0.0277 (18)	0.0272 (16)	0.0290 (17)	−0.0053 (13)	0.0045 (13)	−0.0053 (13)
N6	0.0208 (16)	0.0269 (16)	0.0248 (16)	−0.0070 (12)	0.0013 (13)	−0.0070 (12)
N7	0.0309 (18)	0.0265 (16)	0.0289 (17)	−0.0070 (14)	0.0030 (14)	−0.0035 (13)
N8	0.0258 (17)	0.0317 (17)	0.0275 (17)	−0.0095 (13)	0.0031 (13)	−0.0077 (13)
N9	0.0247 (17)	0.0334 (18)	0.0314 (18)	−0.0077 (14)	0.0025 (14)	−0.0090 (14)
N10	0.0235 (16)	0.0251 (16)	0.0283 (17)	−0.0066 (13)	0.0002 (13)	−0.0056 (13)
N11	0.0295 (18)	0.0260 (16)	0.0284 (17)	−0.0065 (13)	0.0033 (14)	−0.0088 (13)
N12	0.0247 (17)	0.0297 (16)	0.0258 (16)	−0.0069 (13)	0.0013 (13)	−0.0076 (13)
C1	0.0201 (19)	0.031 (2)	0.027 (2)	−0.0043 (15)	0.0059 (15)	−0.0074 (16)
C2	0.031 (2)	0.028 (2)	0.026 (2)	−0.0045 (16)	0.0097 (16)	−0.0016 (15)
C3	0.034 (2)	0.036 (2)	0.032 (2)	−0.0038 (18)	0.0043 (18)	0.0005 (17)
C4	0.043 (3)	0.033 (2)	0.039 (2)	0.0019 (19)	0.009 (2)	0.0008 (18)
C5	0.050 (3)	0.023 (2)	0.044 (3)	−0.0062 (19)	0.018 (2)	−0.0049 (18)
C6	0.046 (3)	0.031 (2)	0.039 (2)	−0.0144 (19)	0.012 (2)	−0.0061 (18)
C7	0.034 (2)	0.0260 (19)	0.027 (2)	−0.0080 (16)	0.0099 (17)	−0.0054 (15)
C8	0.031 (2)	0.0277 (19)	0.0232 (19)	−0.0097 (16)	0.0040 (16)	−0.0067 (15)
C9	0.025 (2)	0.031 (2)	0.028 (2)	−0.0088 (16)	0.0015 (16)	−0.0070 (16)
C10	0.027 (2)	0.034 (2)	0.030 (2)	−0.0088 (17)	−0.0029 (16)	−0.0038 (16)
C11	0.034 (2)	0.043 (2)	0.041 (2)	−0.0170 (19)	−0.0051 (19)	−0.0058 (19)
C12	0.031 (2)	0.047 (3)	0.059 (3)	−0.017 (2)	−0.006 (2)	−0.001 (2)
C13	0.022 (2)	0.047 (3)	0.054 (3)	−0.0054 (19)	0.0044 (19)	−0.006 (2)
C14	0.029 (2)	0.041 (2)	0.039 (2)	−0.0042 (18)	0.0006 (18)	−0.0051 (18)
C15	0.023 (2)	0.035 (2)	0.035 (2)	−0.0081 (16)	0.0000 (16)	−0.0037 (17)
C16	0.0216 (19)	0.0274 (19)	0.030 (2)	−0.0035 (15)	0.0018 (16)	−0.0054 (16)
C17	0.029 (2)	0.0200 (17)	0.028 (2)	−0.0078 (15)	0.0063 (16)	−0.0059 (14)
C18	0.034 (2)	0.0275 (19)	0.029 (2)	−0.0134 (17)	0.0021 (17)	−0.0049 (16)
C19	0.041 (2)	0.031 (2)	0.035 (2)	−0.0103 (18)	0.0033 (19)	−0.0108 (17)
C20	0.055 (3)	0.044 (2)	0.032 (2)	−0.016 (2)	0.002 (2)	−0.0161 (19)
C21	0.052 (3)	0.051 (3)	0.035 (2)	−0.019 (2)	−0.007 (2)	−0.016 (2)
C22	0.039 (2)	0.037 (2)	0.036 (2)	−0.0131 (19)	−0.0072 (19)	−0.0041 (18)
C23	0.030 (2)	0.029 (2)	0.028 (2)	−0.0143 (16)	0.0005 (16)	−0.0053 (16)
C24	0.025 (2)	0.029 (2)	0.027 (2)	−0.0096 (16)	0.0026 (16)	−0.0028 (15)
C25	0.029 (2)	0.0253 (19)	0.028 (2)	−0.0064 (16)	0.0059 (16)	−0.0038 (15)
C26	0.033 (2)	0.031 (2)	0.031 (2)	−0.0106 (17)	0.0075 (17)	−0.0079 (16)
C27	0.042 (2)	0.033 (2)	0.044 (3)	−0.0098 (19)	0.001 (2)	−0.0110 (19)
C28	0.054 (3)	0.036 (2)	0.060 (3)	−0.016 (2)	0.003 (2)	−0.020 (2)
C29	0.053 (3)	0.045 (3)	0.052 (3)	−0.017 (2)	−0.002 (2)	−0.023 (2)
C30	0.033 (2)	0.043 (2)	0.041 (2)	−0.0116 (19)	−0.0017 (19)	−0.0098 (19)
C31	0.032 (2)	0.034 (2)	0.032 (2)	−0.0123 (17)	0.0047 (17)	−0.0086 (17)
C32	0.023 (2)	0.035 (2)	0.030 (2)	−0.0087 (16)	0.0067 (16)	−0.0082 (16)
C33	0.023 (2)	0.030 (2)	0.029 (2)	−0.0039 (16)	0.0034 (16)	−0.0091 (16)
C34	0.029 (2)	0.0277 (19)	0.026 (2)	−0.0024 (16)	0.0037 (16)	−0.0081 (15)
C35	0.034 (2)	0.035 (2)	0.030 (2)	−0.0038 (17)	0.0000 (17)	−0.0120 (17)
C36	0.041 (2)	0.039 (2)	0.027 (2)	0.0008 (19)	−0.0018 (18)	−0.0067 (17)
C37	0.051 (3)	0.028 (2)	0.027 (2)	−0.0072 (19)	0.0083 (19)	−0.0040 (16)
C38	0.039 (2)	0.031 (2)	0.031 (2)	−0.0089 (18)	0.0053 (18)	−0.0078 (17)
C39	0.030 (2)	0.0272 (19)	0.027 (2)	−0.0054 (16)	0.0044 (16)	−0.0096 (16)
C40	0.025 (2)	0.0277 (19)	0.028 (2)	−0.0072 (15)	0.0032 (16)	−0.0102 (15)
C41	0.029 (2)	0.034 (2)	0.0237 (19)	−0.0085 (17)	0.0022 (16)	−0.0103 (16)
C42	0.029 (2)	0.038 (2)	0.027 (2)	−0.0073 (17)	−0.0003 (16)	−0.0110 (16)
C43	0.030 (2)	0.047 (2)	0.036 (2)	−0.0124 (19)	0.0014 (18)	−0.0078 (19)
C44	0.029 (2)	0.059 (3)	0.048 (3)	−0.012 (2)	−0.001 (2)	−0.009 (2)
C45	0.030 (2)	0.055 (3)	0.039 (3)	−0.001 (2)	0.0025 (19)	−0.010 (2)
C46	0.032 (2)	0.042 (2)	0.034 (2)	−0.0022 (18)	−0.0049 (18)	−0.0080 (18)
C47	0.027 (2)	0.038 (2)	0.027 (2)	−0.0052 (17)	0.0012 (16)	−0.0104 (17)
C48	0.030 (2)	0.030 (2)	0.0238 (19)	−0.0068 (16)	0.0026 (16)	−0.0062 (15)
B1	0.020 (2)	0.026 (2)	0.032 (2)	−0.0069 (17)	0.0040 (17)	−0.0105 (18)
B2	0.031 (2)	0.025 (2)	0.030 (2)	−0.0101 (18)	0.0004 (19)	−0.0040 (18)
Cl1	0.0745 (11)	0.0570 (9)	0.0660 (11)	−0.0034 (8)	−0.0059 (8)	−0.0257 (8)
Cl2	0.0632 (11)	0.0838 (12)	0.0820 (13)	−0.0262 (9)	0.0176 (9)	−0.0200 (9)
C1S	0.045 (3)	0.046 (3)	0.046 (3)	0.008 (2)	−0.011 (3)	−0.014 (2)
C2S	0.046 (4)	0.052 (3)	0.053 (4)	0.000 (3)	−0.020 (3)	−0.008 (3)
C3S	0.047 (4)	0.055 (4)	0.057 (4)	−0.003 (3)	−0.007 (3)	−0.029 (3)
C4S	0.056 (4)	0.060 (4)	0.045 (3)	−0.004 (3)	−0.007 (3)	−0.013 (3)
C5S	0.043 (4)	0.069 (4)	0.055 (4)	−0.002 (3)	−0.001 (3)	−0.002 (3)
C6S	0.046 (3)	0.057 (4)	0.046 (3)	−0.006 (3)	−0.013 (3)	0.004 (3)
Cl3	0.0588 (11)	0.0620 (11)	0.0677 (12)	−0.0099 (8)	0.0028 (9)	−0.0078 (9)
Cl4	0.107 (2)	0.141 (2)	0.0879 (18)	0.0560 (17)	−0.0365 (15)	−0.0658 (16)
C7S	0.035 (4)	0.079 (4)	0.043 (3)	0.012 (3)	−0.006 (2)	−0.008 (3)
C8S	0.052 (5)	0.130 (6)	0.039 (4)	0.043 (4)	−0.007 (3)	−0.003 (3)
C9S	0.066 (6)	0.189 (9)	0.061 (6)	0.044 (6)	0.016 (4)	0.037 (5)
C10S	0.128 (11)	0.189 (13)	0.128 (11)	−0.030 (10)	0.046 (7)	0.061 (8)
C11S	0.060 (5)	0.090 (5)	0.127 (7)	−0.007 (4)	−0.006 (4)	0.057 (4)
C12S	0.062 (5)	0.077 (5)	0.067 (5)	−0.018 (4)	−0.006 (3)	0.009 (3)

Geometric parameters (Å, º) top

O1—B1	1.411 (5)	C29—H29A	0.9500
O1—B2	1.411 (5)	C30—C31	1.400 (5)
N1—C24	1.343 (5)	C30—H30A	0.9500
N1—C1	1.355 (4)	C31—C32	1.457 (5)
N2—C1	1.357 (5)	C33—C34	1.462 (5)
N2—C8	1.365 (4)	C34—C35	1.389 (5)
N2—B1	1.510 (5)	C34—C39	1.426 (5)
N3—C8	1.341 (5)	C35—C36	1.388 (6)
N3—C9	1.347 (5)	C35—H35A	0.9500
N4—C16	1.364 (4)	C36—C37	1.394 (6)
N4—C9	1.370 (4)	C36—H36A	0.9500
N4—B1	1.513 (5)	C37—C38	1.391 (6)
N5—C17	1.350 (5)	C37—H37A	0.9500
N5—C16	1.352 (4)	C38—C39	1.389 (5)
N6—C17	1.350 (4)	C38—H38A	0.9500
N6—C24	1.365 (4)	C39—C40	1.461 (5)
N6—B1	1.501 (5)	C41—C42	1.454 (5)
N7—C25	1.336 (5)	C42—C43	1.385 (5)
N7—C48	1.346 (5)	C42—C47	1.418 (5)
N8—C32	1.366 (5)	C43—C44	1.373 (6)
N8—C25	1.374 (5)	C43—H43A	0.9500
N8—B2	1.504 (5)	C44—C45	1.407 (6)
N9—C33	1.341 (5)	C44—H44A	0.9500
N9—C32	1.349 (5)	C45—C46	1.378 (6)
N10—C40	1.360 (4)	C45—H45A	0.9500
N10—C33	1.361 (5)	C46—C47	1.397 (5)
N10—B2	1.504 (5)	C46—H46A	0.9500
N11—C40	1.337 (5)	C47—C48	1.458 (5)
N11—C41	1.347 (5)	Cl1—C1S	1.721 (3)
N12—C48	1.368 (5)	Cl2—C2S	1.711 (3)
N12—C41	1.376 (5)	C1S—C2S	1.3900
N12—B2	1.508 (5)	C1S—C6S	1.3900
C1—C2	1.449 (5)	C2S—C3S	1.3900
C2—C3	1.388 (5)	C3S—C4S	1.3900
C2—C7	1.424 (5)	C3S—H3S	0.9500
C3—C4	1.377 (6)	C4S—C5S	1.3900
C3—H3A	0.9500	C4S—H4S	0.9500
C4—C5	1.394 (6)	C5S—C6S	1.3900
C4—H4A	0.9500	C5S—H5S	0.9500
C5—C6	1.382 (6)	C6S—H6S	0.9500
C5—H5A	0.9500	Cl1B—C1B	1.720 (6)
C6—C7	1.388 (5)	Cl2B—C2B	1.710 (6)
C6—H6A	0.9500	C1B—C6B	1.390 (5)
C7—C8	1.453 (5)	C1B—C2B	1.392 (5)
C9—C10	1.451 (5)	C2B—C3B	1.389 (5)
C10—C11	1.395 (5)	C3B—C4B	1.392 (5)
C10—C15	1.420 (5)	C3B—H3B	0.9500
C11—C12	1.382 (6)	C4B—C5B	1.393 (5)
C11—H11A	0.9500	C4B—H4B	0.9500
C12—C13	1.388 (6)	C5B—C6B	1.391 (5)
C12—H12A	0.9500	C5B—H5B	0.9500
C13—C14	1.383 (6)	C6B—H6B	0.9500
C13—H13A	0.9500	Cl3—C7S	1.713 (4)
C14—C15	1.393 (5)	Cl4—C8S	1.689 (5)
C14—H14A	0.9500	C7S—C8S	1.3900
C15—C16	1.453 (5)	C7S—C12S	1.3900
C17—C18	1.454 (5)	C8S—C9S	1.3900
C18—C19	1.403 (5)	C9S—C10S	1.3900
C18—C23	1.406 (5)	C9S—H9S	0.9500
C19—C20	1.378 (6)	C10S—C11S	1.3900
C19—H19A	0.9500	C10S—H10S	0.9500
C20—C21	1.390 (6)	C11S—C12S	1.3900
C20—H20A	0.9500	C11S—H11S	0.9500
C21—C22	1.381 (6)	C12S—H12S	0.9500
C21—H21A	0.9500	Cl3A—C7A	1.712 (6)
C22—C23	1.404 (5)	Cl4A—C8A	1.685 (6)
C22—H22A	0.9500	C7A—C12A	1.389 (5)
C23—C24	1.457 (5)	C7A—C8A	1.395 (5)
C25—C26	1.458 (5)	C8A—C9A	1.387 (5)
C26—C27	1.392 (5)	C9A—C10A	1.391 (5)
C26—C31	1.412 (5)	C9A—H9A	0.9500
C27—C28	1.384 (6)	C10A—C11A	1.392 (5)
C27—H27A	0.9500	C10A—H10A	0.9500
C28—C29	1.391 (6)	C11A—C12A	1.393 (5)
C28—H28A	0.9500	C11A—H11B	0.9500
C29—C30	1.380 (6)	C12A—H12B	0.9500

B1—O1—B2	132.8 (3)	C36—C35—C34	117.7 (4)
C24—N1—C1	116.7 (3)	C36—C35—H35A	121.1
C1—N2—C8	113.1 (3)	C34—C35—H35A	121.1
C1—N2—B1	122.9 (3)	C35—C36—C37	121.5 (4)
C8—N2—B1	123.5 (3)	C35—C36—H36A	119.2
C8—N3—C9	117.2 (3)	C37—C36—H36A	119.2
C16—N4—C9	112.5 (3)	C38—C37—C36	121.6 (4)
C16—N4—B1	123.2 (3)	C38—C37—H37A	119.2
C9—N4—B1	122.9 (3)	C36—C37—H37A	119.2
C17—N5—C16	116.4 (3)	C39—C38—C37	117.5 (4)
C17—N6—C24	113.2 (3)	C39—C38—H38A	121.2
C17—N6—B1	123.8 (3)	C37—C38—H38A	121.2
C24—N6—B1	122.2 (3)	C38—C39—C34	120.8 (3)
C25—N7—C48	117.1 (3)	C38—C39—C40	132.2 (3)
C32—N8—C25	112.7 (3)	C34—C39—C40	106.9 (3)
C32—N8—B2	122.2 (3)	N11—C40—N10	122.0 (3)
C25—N8—B2	123.5 (3)	N11—C40—C39	131.3 (3)
C33—N9—C32	116.6 (3)	N10—C40—C39	105.6 (3)
C40—N10—C33	113.6 (3)	N11—C41—N12	122.4 (3)
C40—N10—B2	123.4 (3)	N11—C41—C42	129.9 (3)
C33—N10—B2	122.8 (3)	N12—C41—C42	106.1 (3)
C40—N11—C41	117.2 (3)	C43—C42—C47	120.6 (4)
C48—N12—C41	112.0 (3)	C43—C42—C41	131.9 (4)
C48—N12—B2	123.8 (3)	C47—C42—C41	107.2 (3)
C41—N12—B2	122.6 (3)	C44—C43—C42	118.4 (4)
N1—C1—N2	122.1 (3)	C44—C43—H43A	120.8
N1—C1—C2	130.6 (3)	C42—C43—H43A	120.8
N2—C1—C2	106.1 (3)	C43—C44—C45	121.3 (4)
C3—C2—C7	120.9 (3)	C43—C44—H44A	119.4
C3—C2—C1	132.5 (4)	C45—C44—H44A	119.4
C7—C2—C1	106.7 (3)	C46—C45—C44	121.2 (4)
C4—C3—C2	117.9 (4)	C46—C45—H45A	119.4
C4—C3—H3A	121.1	C44—C45—H45A	119.4
C2—C3—H3A	121.1	C45—C46—C47	117.9 (4)
C3—C4—C5	121.5 (4)	C45—C46—H46A	121.1
C3—C4—H4A	119.3	C47—C46—H46A	121.1
C5—C4—H4A	119.3	C46—C47—C42	120.6 (4)
C6—C5—C4	121.3 (4)	C46—C47—C48	131.9 (4)
C6—C5—H5A	119.3	C42—C47—C48	107.1 (3)
C4—C5—H5A	119.3	N7—C48—N12	122.4 (3)
C5—C6—C7	118.2 (4)	N7—C48—C47	129.1 (3)
C5—C6—H6A	120.9	N12—C48—C47	106.3 (3)
C7—C6—H6A	120.9	O1—B1—N6	114.0 (3)
C6—C7—C2	120.1 (4)	O1—B1—N2	117.0 (3)
C6—C7—C8	132.6 (4)	N6—B1—N2	102.9 (3)
C2—C7—C8	107.3 (3)	O1—B1—N4	116.0 (3)
N3—C8—N2	122.0 (3)	N6—B1—N4	102.4 (3)
N3—C8—C7	131.7 (3)	N2—B1—N4	102.6 (3)
N2—C8—C7	105.1 (3)	O1—B2—N10	111.0 (3)
N3—C9—N4	122.8 (3)	O1—B2—N8	118.4 (3)
N3—C9—C10	129.5 (3)	N10—B2—N8	102.8 (3)
N4—C9—C10	106.0 (3)	O1—B2—N12	117.3 (3)
C11—C10—C15	120.7 (4)	N10—B2—N12	102.4 (3)
C11—C10—C9	131.7 (4)	N8—B2—N12	102.9 (3)
C15—C10—C9	107.3 (3)	C2S—C1S—C6S	120.0
C12—C11—C10	117.7 (4)	C2S—C1S—Cl1	121.4 (2)
C12—C11—H11A	121.2	C6S—C1S—Cl1	118.6 (2)
C10—C11—H11A	121.2	C1S—C2S—C3S	120.0
C11—C12—C13	121.7 (4)	C1S—C2S—Cl2	121.2 (2)
C11—C12—H12A	119.1	C3S—C2S—Cl2	118.8 (2)
C13—C12—H12A	119.1	C4S—C3S—C2S	120.0
C14—C13—C12	121.5 (4)	C4S—C3S—H3S	120.0
C14—C13—H13A	119.3	C2S—C3S—H3S	120.0
C12—C13—H13A	119.3	C5S—C4S—C3S	120.0
C13—C14—C15	118.0 (4)	C5S—C4S—H4S	120.0
C13—C14—H14A	121.0	C3S—C4S—H4S	120.0
C15—C14—H14A	121.0	C4S—C5S—C6S	120.0
C14—C15—C10	120.4 (3)	C4S—C5S—H5S	120.0
C14—C15—C16	132.4 (4)	C6S—C5S—H5S	120.0
C10—C15—C16	106.9 (3)	C5S—C6S—C1S	120.0
N5—C16—N4	122.5 (3)	C5S—C6S—H6S	120.0
N5—C16—C15	129.0 (3)	C1S—C6S—H6S	120.0
N4—C16—C15	106.2 (3)	C6B—C1B—C2B	119.8 (8)
N5—C17—N6	122.8 (3)	C6B—C1B—Cl1B	119.5 (8)
N5—C17—C18	129.5 (3)	C2B—C1B—Cl1B	120.0 (7)
N6—C17—C18	105.8 (3)	C3B—C2B—C1B	120.1 (7)
C19—C18—C23	120.9 (3)	C3B—C2B—Cl2B	119.6 (7)
C19—C18—C17	131.3 (4)	C1B—C2B—Cl2B	120.1 (7)
C23—C18—C17	107.5 (3)	C2B—C3B—C4B	119.4 (8)
C20—C19—C18	117.3 (4)	C2B—C3B—H3B	120.3
C20—C19—H19A	121.3	C4B—C3B—H3B	120.3
C18—C19—H19A	121.3	C3B—C4B—C5B	119.5 (8)
C19—C20—C21	121.6 (4)	C3B—C4B—H4B	120.2
C19—C20—H20A	119.2	C5B—C4B—H4B	120.2
C21—C20—H20A	119.2	C6B—C5B—C4B	119.5 (9)
C22—C21—C20	122.2 (4)	C6B—C5B—H5B	120.2
C22—C21—H21A	118.9	C4B—C5B—H5B	120.2
C20—C21—H21A	118.9	C1B—C6B—C5B	119.2 (8)
C21—C22—C23	117.0 (4)	C1B—C6B—H6B	120.4
C21—C22—H22A	121.5	C5B—C6B—H6B	120.4
C23—C22—H22A	121.5	C8S—C7S—C12S	120.0
C22—C23—C18	120.9 (4)	C8S—C7S—Cl3	122.2 (3)
C22—C23—C24	131.8 (4)	C12S—C7S—Cl3	117.8 (3)
C18—C23—C24	106.9 (3)	C9S—C8S—C7S	120.0
N1—C24—N6	123.2 (3)	C9S—C8S—Cl4	119.0 (3)
N1—C24—C23	129.6 (3)	C7S—C8S—Cl4	120.9 (3)
N6—C24—C23	105.5 (3)	C8S—C9S—C10S	120.0
N7—C25—N8	122.9 (3)	C8S—C9S—H9S	120.0
N7—C25—C26	129.5 (3)	C10S—C9S—H9S	120.0
N8—C25—C26	105.6 (3)	C11S—C10S—C9S	120.0
C27—C26—C31	120.9 (4)	C11S—C10S—H10S	120.0
C27—C26—C25	131.7 (4)	C9S—C10S—H10S	120.0
C31—C26—C25	107.1 (3)	C10S—C11S—C12S	120.0
C28—C27—C26	117.6 (4)	C10S—C11S—H11S	120.0
C28—C27—H27A	121.2	C12S—C11S—H11S	120.0
C26—C27—H27A	121.2	C11S—C12S—C7S	120.0
C27—C28—C29	121.8 (4)	C11S—C12S—H12S	120.0
C27—C28—H28A	119.1	C7S—C12S—H12S	120.0
C29—C28—H28A	119.1	C12A—C7A—C8A	119.5 (7)
C30—C29—C28	121.3 (4)	C12A—C7A—Cl3A	118.6 (7)
C30—C29—H29A	119.3	C8A—C7A—Cl3A	120.7 (7)
C28—C29—H29A	119.3	C9A—C8A—C7A	120.1 (5)
C29—C30—C31	118.0 (4)	C9A—C8A—Cl4A	120.5 (6)
C29—C30—H30A	121.0	C7A—C8A—Cl4A	119.4 (6)
C31—C30—H30A	121.0	C8A—C9A—C10A	119.4 (7)
C30—C31—C26	120.5 (4)	C8A—C9A—H9A	120.3
C30—C31—C32	131.7 (4)	C10A—C9A—H9A	120.3
C26—C31—C32	107.6 (3)	C9A—C10A—C11A	119.0 (7)
N9—C32—N8	123.0 (3)	C9A—C10A—H10A	120.5
N9—C32—C31	129.4 (3)	C11A—C10A—H10A	120.5
N8—C32—C31	105.7 (3)	C10A—C11A—C12A	119.8 (7)
N9—C33—N10	122.3 (3)	C10A—C11A—H11B	120.1
N9—C33—C34	131.1 (3)	C12A—C11A—H11B	120.1
N10—C33—C34	105.5 (3)	C7A—C12A—C11A	119.5 (6)
C35—C34—C39	120.7 (3)	C7A—C12A—H12B	120.3
C35—C34—C33	132.3 (3)	C11A—C12A—H12B	120.3
C39—C34—C33	107.0 (3)

(m-oxo-BsubPc-subl) top

Crystal data top

C₄₈H₂₄B₂N₁₂O	F(000) = 1656
M_r = 806.41	D_x = 1.451 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 12572 reflections
a = 25.6932 (18) Å	θ = 2.6–25.0°
b = 8.3375 (5) Å	µ = 0.09 mm⁻¹
c = 20.8860 (16) Å	T = 147 K
β = 124.401 (3)°	Block, purple
V = 3691.6 (4) Å³	0.20 × 0.10 × 0.10 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	3233 independent reflections
Radiation source: fine-focus sealed tube	1908 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.138
Detector resolution: 9 pixels mm^-1	θ_max = 25.0°, θ_min = 2.6°
ϕ scans and ω scans with κ offsets	h = −30→29
Absorption correction: multi-scan multi-scan from symmetry-related measurements SORTAV (Blessing 1995)	k = −9→9
T_min = 0.561, T_max = 1.007	l = −24→24
12572 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.088	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.229	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0855P)² + 8.4419P] where P = (F_o² + 2F_c²)/3
3233 reflections	(Δ/σ)_max = 0.003
285 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₄₈H₂₄B₂N₁₂O	V = 3691.6 (4) Å³
M_r = 806.41	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 25.6932 (18) Å	µ = 0.09 mm⁻¹
b = 8.3375 (5) Å	T = 147 K
c = 20.8860 (16) Å	0.20 × 0.10 × 0.10 mm
β = 124.401 (3)°

Data collection top

Nonius KappaCCD diffractometer	3233 independent reflections
Absorption correction: multi-scan multi-scan from symmetry-related measurements SORTAV (Blessing 1995)	1908 reflections with I > 2σ(I)
T_min = 0.561, T_max = 1.007	R_int = 0.138
12572 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.088	0 restraints
wR(F²) = 0.229	H-atom parameters constrained
S = 1.09	Δρ_max = 0.47 e Å⁻³
3233 reflections	Δρ_min = −0.30 e Å⁻³
285 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.5000	0.3318 (5)	0.2500	0.0452 (12)
N2	0.41066 (18)	0.5153 (4)	0.2130 (2)	0.0412 (10)
N3	0.43519 (17)	0.7531 (4)	0.1732 (2)	0.0426 (10)
N4	0.44415 (17)	0.4995 (4)	0.1290 (2)	0.0422 (10)
N5	0.40166 (18)	0.2919 (5)	0.0340 (2)	0.0453 (10)
N6	0.39229 (17)	0.2795 (4)	0.1412 (2)	0.0415 (10)
N1	0.33673 (17)	0.3235 (4)	0.2002 (2)	0.0426 (10)
C1	0.3674 (2)	0.4657 (6)	0.2265 (3)	0.0433 (12)
C2	0.3504 (2)	0.6078 (6)	0.2524 (3)	0.0443 (12)
C3	0.3105 (2)	0.6313 (6)	0.2762 (3)	0.0485 (13)
H3A	0.2884	0.5442	0.2797	0.058*
C4	0.3036 (2)	0.7865 (6)	0.2946 (3)	0.0509 (13)
H4A	0.2770	0.8055	0.3118	0.061*
C5	0.3351 (2)	0.9143 (6)	0.2882 (3)	0.0531 (14)
H5A	0.3301	1.0186	0.3022	0.064*
C6	0.3730 (2)	0.8944 (6)	0.2624 (3)	0.0474 (13)
H6A	0.3932	0.9836	0.2569	0.057*
C7	0.3814 (2)	0.7395 (5)	0.2443 (3)	0.0424 (12)
C8	0.4155 (2)	0.6785 (5)	0.2127 (3)	0.0417 (12)
C9	0.4457 (2)	0.6625 (5)	0.1289 (3)	0.0419 (12)
C10	0.4447 (2)	0.7086 (6)	0.0610 (3)	0.0455 (12)
C11	0.4460 (2)	0.8566 (6)	0.0318 (3)	0.0500 (13)
H11A	0.4516	0.9528	0.0594	0.060*
C12	0.4387 (2)	0.8596 (7)	−0.0395 (3)	0.0571 (14)
H12A	0.4400	0.9597	−0.0603	0.069*
C13	0.4295 (2)	0.7197 (7)	−0.0811 (3)	0.0579 (15)
H13A	0.4253	0.7259	−0.1293	0.069*
C14	0.4266 (2)	0.5727 (6)	−0.0533 (3)	0.0495 (13)
H14A	0.4190	0.4778	−0.0826	0.059*
C15	0.4349 (2)	0.5663 (6)	0.0182 (3)	0.0461 (12)
C16	0.4301 (2)	0.4356 (6)	0.0608 (3)	0.0434 (12)
C17	0.3789 (2)	0.2233 (5)	0.0722 (3)	0.0429 (12)
C18	0.3258 (2)	0.1120 (5)	0.0426 (3)	0.0412 (12)
C19	0.2935 (2)	0.0207 (5)	−0.0248 (3)	0.0440 (12)
H19A	0.3061	0.0165	−0.0596	0.053*
C20	0.2417 (2)	−0.0640 (5)	−0.0384 (3)	0.0478 (13)
H20A	0.2195	−0.1319	−0.0826	0.057*
C21	0.2214 (2)	−0.0529 (5)	0.0105 (3)	0.0464 (12)
H21A	0.1853	−0.1118	−0.0015	0.056*
C22	0.2526 (2)	0.0420 (5)	0.0764 (3)	0.0451 (12)
H22A	0.2382	0.0504	0.1094	0.054*
C23	0.3060 (2)	0.1249 (6)	0.0927 (3)	0.0424 (12)
C24	0.3466 (2)	0.2403 (5)	0.1531 (3)	0.0416 (12)
B1	0.4429 (2)	0.4029 (6)	0.1893 (3)	0.0427 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.043 (3)	0.040 (2)	0.044 (3)	0.000	0.019 (2)	0.000
N2	0.044 (2)	0.038 (2)	0.043 (2)	−0.0003 (17)	0.025 (2)	0.0019 (18)
N3	0.041 (2)	0.040 (2)	0.045 (2)	0.0019 (17)	0.023 (2)	0.0017 (19)
N4	0.039 (2)	0.038 (2)	0.047 (3)	0.0004 (17)	0.023 (2)	−0.0008 (19)
N5	0.039 (2)	0.046 (2)	0.048 (3)	0.0029 (18)	0.023 (2)	−0.0012 (19)
N6	0.040 (2)	0.042 (2)	0.039 (2)	0.0041 (17)	0.021 (2)	0.0033 (18)
N1	0.037 (2)	0.043 (2)	0.047 (2)	0.0013 (17)	0.023 (2)	0.0033 (19)
C1	0.043 (3)	0.048 (3)	0.033 (3)	0.002 (2)	0.019 (2)	0.004 (2)
C2	0.040 (3)	0.049 (3)	0.038 (3)	0.001 (2)	0.018 (2)	−0.002 (2)
C3	0.042 (3)	0.058 (3)	0.041 (3)	−0.004 (2)	0.021 (3)	0.000 (2)
C4	0.052 (3)	0.056 (3)	0.048 (3)	0.013 (3)	0.031 (3)	0.002 (3)
C5	0.049 (3)	0.047 (3)	0.053 (3)	0.007 (2)	0.023 (3)	−0.003 (3)
C6	0.044 (3)	0.045 (3)	0.040 (3)	0.004 (2)	0.016 (3)	−0.002 (2)
C7	0.036 (3)	0.050 (3)	0.031 (3)	0.003 (2)	0.013 (2)	0.001 (2)
C8	0.035 (3)	0.041 (3)	0.036 (3)	0.002 (2)	0.012 (2)	0.001 (2)
C9	0.028 (3)	0.040 (3)	0.045 (3)	0.0002 (19)	0.013 (2)	0.001 (2)
C10	0.038 (3)	0.046 (3)	0.052 (3)	−0.002 (2)	0.025 (3)	0.004 (2)
C11	0.041 (3)	0.054 (3)	0.052 (3)	−0.001 (2)	0.024 (3)	0.003 (3)
C12	0.053 (3)	0.061 (4)	0.063 (4)	−0.001 (3)	0.035 (3)	0.011 (3)
C13	0.054 (3)	0.073 (4)	0.052 (3)	−0.010 (3)	0.033 (3)	0.006 (3)
C14	0.039 (3)	0.063 (3)	0.040 (3)	−0.005 (2)	0.018 (2)	−0.001 (3)
C15	0.039 (3)	0.055 (3)	0.044 (3)	−0.004 (2)	0.023 (2)	−0.001 (2)
C16	0.037 (3)	0.043 (3)	0.053 (3)	0.002 (2)	0.027 (3)	−0.002 (2)
C17	0.040 (3)	0.043 (3)	0.048 (3)	0.006 (2)	0.026 (3)	0.000 (2)
C18	0.032 (3)	0.039 (3)	0.041 (3)	0.002 (2)	0.014 (2)	0.000 (2)
C19	0.042 (3)	0.040 (3)	0.047 (3)	0.006 (2)	0.023 (3)	0.005 (2)
C20	0.044 (3)	0.039 (3)	0.048 (3)	0.000 (2)	0.019 (3)	−0.003 (2)
C21	0.038 (3)	0.039 (3)	0.052 (3)	0.000 (2)	0.019 (3)	0.002 (2)
C22	0.038 (3)	0.043 (3)	0.052 (3)	0.005 (2)	0.024 (3)	0.003 (2)
C23	0.032 (3)	0.047 (3)	0.042 (3)	−0.002 (2)	0.017 (2)	−0.001 (2)
C24	0.038 (3)	0.043 (3)	0.045 (3)	0.005 (2)	0.024 (3)	0.005 (2)
B1	0.036 (3)	0.040 (3)	0.048 (4)	−0.005 (2)	0.021 (3)	−0.003 (3)

Geometric parameters (Å, º) top

O1—B1ⁱ	1.418 (6)	C6—C7	1.396 (6)
O1—B1	1.418 (6)	C7—C8	1.455 (6)
N2—C1	1.356 (6)	C9—C10	1.455 (7)
N2—C8	1.366 (6)	C10—C11	1.386 (7)
N2—B1	1.508 (7)	C10—C15	1.419 (7)
N3—C8	1.341 (6)	C11—H11A	0.9500
N3—C9	1.335 (6)	C11—C12	1.392 (7)
N4—C9	1.360 (6)	C12—H12A	0.9500
N4—C16	1.362 (6)	C12—C13	1.392 (7)
N4—B1	1.511 (7)	C13—H13A	0.9500
N5—C16	1.349 (6)	C13—C14	1.376 (7)
N5—C17	1.353 (6)	C14—H14A	0.9500
N6—C17	1.362 (6)	C14—C15	1.385 (7)
N6—C24	1.371 (6)	C15—C16	1.456 (7)
N6—B1	1.510 (6)	C17—C18	1.466 (6)
N1—C1	1.356 (6)	C18—C19	1.389 (6)
N1—C24	1.340 (6)	C18—C23	1.403 (6)
C1—C2	1.467 (6)	C19—H19A	0.9500
C2—C3	1.383 (7)	C19—C20	1.385 (7)
C2—C7	1.421 (6)	C20—H20A	0.9500
C3—H3A	0.9500	C20—C21	1.389 (7)
C3—C4	1.389 (7)	C21—H21A	0.9500
C4—H4A	0.9500	C21—C22	1.384 (7)
C4—C5	1.389 (7)	C22—H22A	0.9500
C5—H5A	0.9500	C22—C23	1.395 (6)
C5—C6	1.364 (7)	C23—C24	1.455 (6)
C6—H6A	0.9500

B1ⁱ—O1—B1	130.6 (5)	C11—C12—H12A	119.2
C1—N2—C8	113.1 (4)	C13—C12—C11	121.7 (5)
C1—N2—B1	123.1 (4)	C13—C12—H12A	119.2
C8—N2—B1	123.3 (4)	C12—C13—H13A	119.5
C9—N3—C8	117.3 (4)	C14—C13—C12	120.9 (5)
C9—N4—C16	112.3 (4)	C14—C13—H13A	119.5
C9—N4—B1	123.2 (4)	C13—C14—H14A	120.8
C16—N4—B1	123.0 (4)	C13—C14—C15	118.5 (5)
C16—N5—C17	116.3 (4)	C15—C14—H14A	120.8
C17—N6—C24	112.4 (4)	C10—C15—C16	106.6 (4)
C17—N6—B1	123.1 (4)	C14—C15—C10	120.8 (5)
C24—N6—B1	123.0 (4)	C14—C15—C16	132.3 (5)
C24—N1—C1	116.3 (4)	N4—C16—C15	106.4 (4)
N2—C1—N1	122.6 (4)	N5—C16—N4	122.9 (4)
N2—C1—C2	106.2 (4)	N5—C16—C15	128.6 (5)
N1—C1—C2	129.0 (4)	N5—C17—N6	122.8 (4)
C3—C2—C1	133.0 (5)	N5—C17—C18	128.9 (4)
C3—C2—C7	120.8 (4)	N6—C17—C18	106.4 (4)
C7—C2—C1	106.1 (4)	C19—C18—C17	131.0 (5)
C2—C3—H3A	121.1	C19—C18—C23	122.4 (4)
C2—C3—C4	117.9 (5)	C23—C18—C17	106.2 (4)
C4—C3—H3A	121.1	C18—C19—H19A	121.8
C3—C4—H4A	119.5	C20—C19—C18	116.3 (5)
C3—C4—C5	121.1 (5)	C20—C19—H19A	121.8
C5—C4—H4A	119.5	C19—C20—H20A	119.0
C4—C5—H5A	119.0	C19—C20—C21	122.1 (5)
C6—C5—C4	122.0 (5)	C21—C20—H20A	119.0
C6—C5—H5A	119.0	C20—C21—H21A	119.3
C5—C6—H6A	120.9	C22—C21—C20	121.5 (4)
C5—C6—C7	118.2 (5)	C22—C21—H21A	119.3
C7—C6—H6A	120.9	C21—C22—H22A	121.2
C2—C7—C8	107.7 (4)	C21—C22—C23	117.6 (5)
C6—C7—C2	120.1 (4)	C23—C22—H22A	121.2
C6—C7—C8	132.1 (5)	C18—C23—C24	108.3 (4)
N2—C8—C7	105.4 (4)	C22—C23—C18	120.0 (4)
N3—C8—N2	122.1 (4)	C22—C23—C24	131.5 (4)
N3—C8—C7	130.6 (4)	N6—C24—C23	105.5 (4)
N3—C9—N4	123.2 (4)	N1—C24—N6	123.2 (4)
N3—C9—C10	128.8 (4)	N1—C24—C23	129.7 (4)
N4—C9—C10	106.3 (4)	O1—B1—N2	116.6 (4)
C11—C10—C9	132.3 (5)	O1—B1—N4	118.0 (4)
C11—C10—C15	120.5 (5)	O1—B1—N6	112.2 (4)
C15—C10—C9	107.0 (4)	N2—B1—N4	102.6 (4)
C10—C11—H11A	121.2	N2—B1—N6	102.5 (4)
C10—C11—C12	117.7 (5)	N6—B1—N4	102.9 (4)
C12—C11—H11A	121.2

Symmetry code: (i) −x+1, y, −z+1/2.

Experimental details

	(H2O-m-oxo-BsubPc)	(DCB-m-oxo-BsubPc)	(m-oxo-BsubPc-subl)
Crystal data
Chemical formula	C₄₈H₂₄B₂N₁₂O·0.25(H₂O)	C₄₈H₂₄B₂N₁₂O·2(C₆H₄Cl₂)	C₄₈H₂₄B₂N₁₂O
M_r	810.92	1100.40	806.41
Crystal system, space group	Triclinic, P1	Triclinic, P1	Monoclinic, C2/c
Temperature (K)	150	150	147
a, b, c (Å)	10.4180 (3), 13.4413 (6), 13.9207 (6)	11.3894 (3), 13.2623 (3), 17.6618 (6)	25.6932 (18), 8.3375 (5), 20.8860 (16)
α, β, γ (°)	87.5640 (19), 77.298 (2), 88.101 (3)	78.3470 (16), 85.6160 (13), 76.7400 (17)	90, 124.401 (3), 90
V (Å³)	1899.35 (13)	2541.89 (12)	3691.6 (4)
Z	2	2	4
Radiation type	Mo Kα	Mo Kα	Mo Kα
µ (mm⁻¹)	0.09	0.29	0.09
Crystal size (mm)	0.30 × 0.25 × 0.20	0.34 × 0.16 × 0.08	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Nonius KappaCCD diffractometer	Nonius KappaCCD diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan multi-scan from symmetry-related measurements SORTAV (Blessing 1995)	Multi-scan multi-scan from symmetry-related measurements SORTAV (Blessing 1995)	Multi-scan multi-scan from symmetry-related measurements SORTAV (Blessing 1995)
T_min, T_max	0.561, 0.653	0.808, 0.985	0.561, 1.007
No. of measured, independent and observed [I > 2σ(I)] reflections	35416, 8597, 3742	26858, 11383, 6168	12572, 3233, 1908
R_int	0.113	0.076	0.138
(sin θ/λ)_max (Å⁻¹)	0.648	0.650	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.214, 0.96	0.085, 0.217, 1.01	0.088, 0.229, 1.09
No. of reflections	8597	11383	3233
No. of parameters	578	738	285
No. of restraints	0	48	0
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.29	0.83, −0.50	0.47, −0.30

Computer programs: Collect (Nonius B.V., 1997-2002), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SIR92 (Altomare et al., 1994), SHELXTL V6.1 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL V6.1.

Hydrogen-bond geometry (Å, º) for (H2O-m-oxo-BsubPc) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···N5ⁱ	0.84	2.20	3.038 (13)	179.5
O1W—H1WB···N3	0.84	2.11	2.946 (13)	179.6

Symmetry code: (i) −x+1, −y+1, −z.

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