6,6′-[(3,3′-Di-tert-butyl-5,5′-dimeth­oxy-1,1′-biphenyl-2,2′-di­yl)bis(oxy)]bis­(dibenzo[d,f][1,3,2]dioxaphosphepine) benzene monosolvate

Leidecker, B.N.; Kubis, C.; Spannenberg, A.; Franke, R.; Börner, A.

doi:10.1107/S2414314619016365

6,6′-[(3,3′-Di-tert-butyl-5,5′-dimethoxy-1,1′-biphenyl-2,2′-diyl)bis(oxy)]bis(dibenzo[d,f][1,3,2]dioxaphosphepine) benzene monosolvate

B. N. Leidecker, C. Kubis, A. Spannenberg, R. Franke and A. Börner

The crystal structure of the benzene monosolvate of the well known organic diphosphite ligand BIPHEPHOS, C₄₆H₄₄O₈P₂·C₆H₆, is reported for the first time. Single crystals of BIPHEPHOS were obtained from a benzene solution after layering with n-heptane at room temperature. One specific property of this type of diphosphite structure is the twisting of the biphenyl units. In the crystal, C—H

π contacts and π–π stacking interactions [centroid-to-centroid distance = 3.8941 (15) Å] are observed.

Keywords: crystal structure; diphosphite; BIPHEPHOS; biphenyl unit.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314619016365/rz4035sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2414314619016365/rz4035Isup2.hkl Contains datablock I

CCDC reference: 1970077

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.004 Å
R factor = 0.040
wR factor = 0.107
Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.595         29 Report

Alert level G
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O1             120.6 Degree
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O2             119.4 Degree
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O3             125.5 Degree
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O4             116.9 Degree
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O5             115.9 Degree
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O6             125.6 Degree
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        62% Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         10 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

6,6'-[(3,3'-Di-tert-butyl-5,5'-dimethoxy-1,1'-biphenyl-2,2'-diyl)bis(oxy)]bis(dibenzo[d,f][1,3,2]dioxaphosphepine) benzene monosolvate top

Crystal data top

C₄₆H₄₄O₈P₂·C₆H₆	F(000) = 1824
M_r = 864.86	D_x = 1.309 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
a = 25.1072 (5) Å	Cell parameters from 4431 reflections
b = 8.8634 (2) Å	θ = 3.8–66.5°
c = 21.3401 (4) Å	µ = 1.36 mm⁻¹
β = 112.4441 (12)°	T = 150 K
V = 4389.20 (16) Å³	Needle, colourless
Z = 4	0.34 × 0.04 × 0.04 mm

Data collection top

Bruker APEXII CCD diffractometer	7745 independent reflections
Radiation source: microfocus	5805 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.067
Detector resolution: 8.3333 pixels mm^-1	θ_max = 66.7°, θ_min = 1.9°
φ and ω scans	h = −29→29
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −10→9
T_min = 0.80, T_max = 0.95	l = −25→25
41898 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.107	w = 1/[σ²(F_o²) + (0.0532P)² + 0.4402P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
7745 reflections	Δρ_max = 0.25 e Å⁻³
567 parameters	Δρ_min = −0.34 e Å⁻³

Special details top

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

Refinement. All H atoms were placed geometrically and refined using a riding atom approximation, with C–H = 0.95–0.98 Å, and with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(C) for methyl H atoms. A rotating model was used for the methyl groups.

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

	x	y	z	U_iso*/U_eq
C1	0.21470 (8)	0.4417 (2)	0.51667 (10)	0.0260 (4)
C2	0.15970 (9)	0.3898 (3)	0.47514 (10)	0.0296 (4)
C3	0.11333 (9)	0.4728 (3)	0.47748 (10)	0.0318 (4)
H3	0.0754	0.4417	0.4499	0.038*
C4	0.12035 (9)	0.5992 (3)	0.51846 (10)	0.0318 (4)
C5	0.17481 (9)	0.6423 (2)	0.56151 (10)	0.0290 (4)
H5	0.1798	0.7261	0.5909	0.035*
C6	0.22288 (8)	0.5612 (2)	0.56154 (9)	0.0260 (4)
C7	0.28090 (8)	0.6109 (2)	0.61018 (9)	0.0257 (4)
C8	0.29895 (9)	0.7562 (2)	0.60285 (9)	0.0275 (4)
H8	0.2752	0.8192	0.5671	0.033*
C9	0.35139 (9)	0.8083 (2)	0.64762 (10)	0.0271 (4)
C10	0.38784 (8)	0.7113 (2)	0.69685 (10)	0.0274 (4)
H10	0.4253	0.7457	0.7246	0.033*
C11	0.37152 (8)	0.5665 (2)	0.70686 (9)	0.0255 (4)
C12	0.31566 (8)	0.5203 (2)	0.66410 (9)	0.0248 (4)
C13	0.14907 (9)	0.2501 (3)	0.42951 (11)	0.0357 (5)
C14	0.18159 (10)	0.1141 (3)	0.47133 (12)	0.0382 (5)
H14A	0.2231	0.1340	0.4890	0.057*
H14B	0.1731	0.0241	0.4425	0.057*
H14C	0.1693	0.0974	0.5092	0.057*
C15	0.16772 (11)	0.2851 (3)	0.37019 (11)	0.0430 (6)
H15A	0.1452	0.3702	0.3440	0.065*
H15B	0.1611	0.1962	0.3408	0.065*
H15C	0.2088	0.3110	0.3880	0.065*
C16	0.08521 (11)	0.2061 (3)	0.39926 (15)	0.0552 (7)
H16A	0.0713	0.1908	0.4359	0.083*
H16B	0.0806	0.1125	0.3732	0.083*
H16C	0.0630	0.2868	0.3693	0.083*
C17	0.07469 (11)	0.7922 (3)	0.55768 (15)	0.0536 (7)
H17A	0.0915	0.7573	0.6048	0.080*
H17B	0.0364	0.8344	0.5484	0.080*
H17C	0.0995	0.8700	0.5504	0.080*
C18	0.33003 (10)	1.0591 (2)	0.60870 (11)	0.0333 (5)
H18A	0.3148	1.0291	0.5609	0.050*
H18B	0.3483	1.1585	0.6135	0.050*
H18C	0.2985	1.0639	0.6250	0.050*
C19	0.41356 (8)	0.4679 (2)	0.76405 (10)	0.0278 (4)
C20	0.39320 (9)	0.4608 (3)	0.82366 (10)	0.0317 (4)
H20A	0.3545	0.4168	0.8080	0.048*
H20B	0.3923	0.5629	0.8409	0.048*
H20C	0.4199	0.3982	0.8599	0.048*
C21	0.47487 (9)	0.5340 (3)	0.79171 (11)	0.0360 (5)
H21A	0.5011	0.4640	0.8247	0.054*
H21B	0.4748	0.6310	0.8138	0.054*
H21C	0.4878	0.5492	0.7542	0.054*
C22	0.41810 (9)	0.3085 (3)	0.73876 (10)	0.0317 (4)
H22A	0.4303	0.3145	0.7003	0.048*
H22B	0.3805	0.2587	0.7244	0.048*
H22C	0.4465	0.2503	0.7754	0.048*
C23	0.42077 (9)	0.4076 (3)	0.56208 (10)	0.0300 (4)
C24	0.45812 (9)	0.5236 (3)	0.59366 (10)	0.0343 (5)
H24	0.4453	0.6070	0.6121	0.041*
C25	0.51494 (10)	0.5166 (3)	0.59814 (11)	0.0397 (5)
H25	0.5411	0.5958	0.6194	0.048*
C26	0.53311 (9)	0.3941 (3)	0.57156 (11)	0.0408 (6)
H26	0.5718	0.3895	0.5746	0.049*
C27	0.49539 (9)	0.2779 (3)	0.54057 (11)	0.0368 (5)
H27	0.5086	0.1939	0.5229	0.044*
C28	0.43789 (9)	0.2825 (3)	0.53483 (10)	0.0310 (4)
C29	0.39772 (9)	0.1581 (3)	0.50225 (10)	0.0309 (4)
C30	0.41526 (10)	0.0076 (3)	0.51498 (11)	0.0352 (5)
H30	0.4534	−0.0142	0.5456	0.042*
C31	0.37855 (10)	−0.1101 (3)	0.48411 (11)	0.0385 (5)
H31	0.3912	−0.2114	0.4946	0.046*
C32	0.32335 (10)	−0.0804 (3)	0.43777 (11)	0.0375 (5)
H32	0.2984	−0.1613	0.4158	0.045*
C33	0.30467 (9)	0.0682 (3)	0.42360 (10)	0.0332 (5)
H33	0.2672	0.0895	0.3912	0.040*
C34	0.34123 (9)	0.1848 (3)	0.45714 (10)	0.0293 (4)
C35	0.15006 (9)	0.2095 (3)	0.64810 (10)	0.0298 (4)
C36	0.09582 (10)	0.2675 (3)	0.61247 (11)	0.0363 (5)
H36	0.0911	0.3526	0.5838	0.044*
C37	0.04799 (10)	0.2002 (3)	0.61888 (12)	0.0401 (5)
H37	0.0105	0.2392	0.5947	0.048*
C38	0.05564 (9)	0.0756 (3)	0.66094 (12)	0.0375 (5)
H38	0.0231	0.0287	0.6651	0.045*
C39	0.11007 (9)	0.0195 (3)	0.69661 (11)	0.0330 (5)
H39	0.1147	−0.0653	0.7254	0.040*
C40	0.15884 (9)	0.0861 (2)	0.69093 (10)	0.0288 (4)
C41	0.21719 (9)	0.0226 (2)	0.72726 (10)	0.0279 (4)
C42	0.22625 (9)	−0.1325 (3)	0.73141 (10)	0.0320 (4)
H42	0.1944	−0.1984	0.7113	0.038*
C43	0.28060 (10)	−0.1929 (3)	0.76411 (11)	0.0369 (5)
H43	0.2859	−0.2992	0.7664	0.044*
C44	0.32739 (10)	−0.0979 (3)	0.79350 (11)	0.0372 (5)
H44	0.3649	−0.1391	0.8151	0.045*
C45	0.31965 (9)	0.0563 (3)	0.79145 (10)	0.0334 (5)
H45	0.3516	0.1213	0.8126	0.040*
C46	0.26507 (9)	0.1158 (2)	0.75833 (9)	0.0284 (4)
C47	0.04143 (12)	0.7196 (4)	0.77065 (14)	0.0537 (7)
H47	0.0019	0.7458	0.7563	0.064*
C48	0.05877 (12)	0.6181 (4)	0.73342 (14)	0.0540 (7)
H48	0.0311	0.5740	0.6937	0.065*
C49	0.11611 (13)	0.5804 (3)	0.75358 (15)	0.0550 (7)
H49	0.1281	0.5103	0.7280	0.066*
C50	0.15594 (13)	0.6450 (4)	0.81117 (17)	0.0627 (9)
H50	0.1956	0.6203	0.8252	0.075*
C51	0.13798 (15)	0.7463 (4)	0.84858 (15)	0.0629 (8)
H51	0.1654	0.7903	0.8885	0.076*
C52	0.08077 (14)	0.7832 (4)	0.82824 (14)	0.0590 (7)
H52	0.0685	0.8524	0.8540	0.071*
O1	0.26355 (6)	0.36536 (16)	0.51544 (7)	0.0273 (3)
O2	0.36542 (6)	0.40936 (17)	0.56232 (7)	0.0294 (3)
O3	0.32105 (6)	0.33231 (17)	0.44072 (7)	0.0309 (3)
O4	0.29329 (6)	0.38073 (16)	0.67427 (7)	0.0265 (3)
O5	0.19750 (6)	0.27103 (17)	0.63783 (7)	0.0309 (3)
O6	0.25769 (6)	0.27110 (17)	0.76141 (7)	0.0310 (3)
O7	0.06992 (7)	0.6688 (2)	0.51339 (8)	0.0427 (4)
O8	0.37168 (7)	0.95099 (17)	0.64772 (7)	0.0337 (3)
P1	0.31057 (2)	0.45307 (6)	0.49248 (2)	0.02799 (13)
P2	0.23811 (2)	0.38617 (6)	0.69709 (3)	0.02787 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0238 (9)	0.0298 (11)	0.0245 (9)	0.0053 (8)	0.0094 (8)	0.0046 (8)
C2	0.0302 (10)	0.0345 (12)	0.0224 (9)	0.0016 (8)	0.0081 (8)	−0.0001 (8)
C3	0.0246 (10)	0.0404 (13)	0.0268 (10)	0.0017 (8)	0.0057 (8)	−0.0021 (8)
C4	0.0266 (10)	0.0397 (13)	0.0273 (10)	0.0085 (9)	0.0083 (8)	0.0012 (9)
C5	0.0301 (10)	0.0300 (11)	0.0259 (9)	0.0030 (8)	0.0096 (8)	−0.0008 (8)
C6	0.0268 (10)	0.0276 (11)	0.0231 (9)	0.0009 (8)	0.0090 (8)	0.0032 (7)
C7	0.0267 (10)	0.0297 (11)	0.0229 (9)	0.0006 (8)	0.0119 (8)	−0.0013 (7)
C8	0.0307 (10)	0.0286 (11)	0.0228 (9)	0.0024 (8)	0.0100 (8)	0.0026 (8)
C9	0.0310 (10)	0.0268 (11)	0.0258 (9)	−0.0033 (8)	0.0132 (8)	−0.0003 (8)
C10	0.0258 (10)	0.0332 (12)	0.0237 (9)	−0.0031 (8)	0.0100 (8)	−0.0029 (8)
C11	0.0263 (10)	0.0294 (11)	0.0241 (9)	0.0004 (8)	0.0133 (8)	−0.0007 (7)
C12	0.0269 (10)	0.0255 (11)	0.0248 (9)	−0.0008 (8)	0.0131 (8)	−0.0010 (7)
C13	0.0310 (11)	0.0398 (13)	0.0325 (10)	0.0000 (9)	0.0079 (9)	−0.0093 (9)
C14	0.0420 (12)	0.0331 (12)	0.0401 (12)	−0.0030 (9)	0.0162 (10)	−0.0069 (9)
C15	0.0471 (14)	0.0492 (15)	0.0258 (10)	0.0085 (11)	0.0061 (10)	−0.0075 (9)
C16	0.0358 (13)	0.0578 (18)	0.0619 (17)	−0.0049 (11)	0.0075 (12)	−0.0290 (14)
C17	0.0395 (14)	0.0598 (18)	0.0567 (15)	0.0138 (12)	0.0130 (12)	−0.0185 (13)
C18	0.0458 (13)	0.0247 (11)	0.0308 (10)	0.0010 (9)	0.0162 (9)	0.0020 (8)
C19	0.0261 (10)	0.0337 (12)	0.0229 (9)	0.0010 (8)	0.0086 (8)	0.0018 (8)
C20	0.0336 (11)	0.0388 (12)	0.0225 (9)	0.0013 (9)	0.0105 (8)	0.0014 (8)
C21	0.0276 (11)	0.0433 (13)	0.0328 (10)	−0.0002 (9)	0.0069 (9)	0.0054 (9)
C22	0.0328 (11)	0.0356 (12)	0.0266 (10)	0.0062 (9)	0.0112 (8)	0.0029 (8)
C23	0.0276 (10)	0.0404 (13)	0.0245 (9)	0.0022 (8)	0.0128 (8)	0.0025 (8)
C24	0.0343 (11)	0.0431 (13)	0.0269 (10)	−0.0024 (9)	0.0133 (9)	−0.0038 (9)
C25	0.0297 (11)	0.0571 (16)	0.0311 (11)	−0.0083 (10)	0.0104 (9)	−0.0037 (10)
C26	0.0265 (11)	0.0679 (17)	0.0294 (10)	−0.0005 (10)	0.0122 (9)	−0.0010 (10)
C27	0.0316 (11)	0.0525 (15)	0.0287 (10)	0.0071 (10)	0.0144 (9)	0.0026 (9)
C28	0.0307 (10)	0.0397 (13)	0.0250 (9)	0.0054 (9)	0.0134 (8)	0.0037 (8)
C29	0.0340 (11)	0.0380 (12)	0.0255 (9)	0.0045 (9)	0.0169 (9)	0.0002 (8)
C30	0.0366 (11)	0.0419 (13)	0.0299 (10)	0.0095 (9)	0.0158 (9)	0.0003 (9)
C31	0.0487 (13)	0.0351 (13)	0.0383 (11)	0.0065 (10)	0.0238 (11)	0.0002 (9)
C32	0.0425 (13)	0.0394 (13)	0.0359 (11)	−0.0028 (10)	0.0207 (10)	−0.0079 (9)
C33	0.0347 (11)	0.0418 (13)	0.0253 (9)	0.0018 (9)	0.0140 (9)	−0.0031 (8)
C34	0.0346 (11)	0.0345 (12)	0.0232 (9)	0.0051 (9)	0.0161 (8)	0.0013 (8)
C35	0.0290 (10)	0.0349 (12)	0.0268 (9)	−0.0040 (8)	0.0121 (8)	−0.0025 (8)
C36	0.0324 (11)	0.0399 (13)	0.0340 (11)	−0.0007 (9)	0.0099 (9)	0.0035 (9)
C37	0.0282 (11)	0.0482 (15)	0.0418 (12)	0.0007 (9)	0.0111 (10)	−0.0012 (10)
C38	0.0291 (11)	0.0461 (14)	0.0403 (11)	−0.0059 (9)	0.0167 (9)	−0.0050 (10)
C39	0.0352 (11)	0.0360 (13)	0.0323 (10)	−0.0048 (9)	0.0179 (9)	−0.0027 (9)
C40	0.0282 (10)	0.0344 (12)	0.0255 (9)	−0.0032 (8)	0.0121 (8)	−0.0046 (8)
C41	0.0311 (10)	0.0327 (12)	0.0239 (9)	−0.0021 (8)	0.0149 (8)	−0.0015 (8)
C42	0.0342 (11)	0.0349 (12)	0.0287 (10)	−0.0028 (9)	0.0139 (9)	−0.0030 (8)
C43	0.0430 (12)	0.0338 (13)	0.0338 (11)	0.0029 (9)	0.0147 (10)	−0.0019 (9)
C44	0.0332 (11)	0.0451 (14)	0.0310 (10)	0.0078 (10)	0.0099 (9)	0.0001 (9)
C45	0.0317 (11)	0.0438 (13)	0.0238 (9)	−0.0033 (9)	0.0095 (8)	−0.0029 (8)
C46	0.0324 (10)	0.0332 (11)	0.0221 (9)	−0.0015 (8)	0.0131 (8)	0.0000 (8)
C47	0.0491 (15)	0.0670 (19)	0.0527 (15)	−0.0009 (13)	0.0281 (13)	0.0081 (13)
C48	0.0528 (16)	0.0603 (18)	0.0471 (14)	−0.0054 (13)	0.0170 (12)	0.0015 (12)
C49	0.0605 (17)	0.0547 (18)	0.0553 (16)	0.0096 (13)	0.0284 (14)	0.0104 (13)
C50	0.0435 (15)	0.068 (2)	0.072 (2)	0.0043 (13)	0.0163 (14)	0.0379 (17)
C51	0.071 (2)	0.061 (2)	0.0418 (14)	−0.0161 (15)	0.0046 (14)	0.0121 (13)
C52	0.074 (2)	0.0626 (19)	0.0441 (14)	−0.0003 (15)	0.0271 (14)	0.0040 (13)
O1	0.0252 (7)	0.0294 (8)	0.0279 (7)	0.0021 (5)	0.0109 (6)	0.0002 (5)
O2	0.0253 (7)	0.0385 (9)	0.0265 (7)	0.0002 (6)	0.0122 (6)	−0.0024 (6)
O3	0.0357 (8)	0.0337 (8)	0.0245 (7)	0.0034 (6)	0.0129 (6)	0.0021 (6)
O4	0.0268 (7)	0.0266 (7)	0.0274 (7)	−0.0005 (5)	0.0120 (6)	0.0007 (5)
O5	0.0300 (7)	0.0366 (8)	0.0263 (7)	−0.0065 (6)	0.0111 (6)	0.0007 (6)
O6	0.0363 (8)	0.0314 (8)	0.0262 (7)	−0.0050 (6)	0.0131 (6)	−0.0023 (6)
O7	0.0274 (8)	0.0520 (11)	0.0421 (9)	0.0098 (7)	0.0058 (7)	−0.0125 (7)
O8	0.0359 (8)	0.0289 (8)	0.0325 (7)	−0.0056 (6)	0.0089 (6)	0.0040 (6)
P1	0.0297 (3)	0.0298 (3)	0.0263 (2)	0.0013 (2)	0.0127 (2)	0.00127 (19)
P2	0.0283 (3)	0.0292 (3)	0.0284 (2)	−0.0014 (2)	0.0133 (2)	−0.0002 (2)

Geometric parameters (Å, º) top

C1—C6	1.390 (3)	C25—C26	1.381 (4)
C1—C2	1.403 (3)	C25—H25	0.9500
C1—O1	1.409 (2)	C26—C27	1.384 (4)
C2—C3	1.394 (3)	C26—H26	0.9500
C2—C13	1.534 (3)	C27—C28	1.402 (3)
C3—C4	1.390 (3)	C27—H27	0.9500
C3—H3	0.9500	C28—C29	1.476 (3)
C4—O7	1.375 (3)	C29—C34	1.397 (3)
C4—C5	1.379 (3)	C29—C30	1.398 (3)
C5—C6	1.404 (3)	C30—C31	1.381 (4)
C5—H5	0.9500	C30—H30	0.9500
C6—C7	1.496 (3)	C31—C32	1.386 (3)
C7—C8	1.394 (3)	C31—H31	0.9500
C7—C12	1.401 (3)	C32—C33	1.393 (3)
C8—C9	1.378 (3)	C32—H32	0.9500
C8—H8	0.9500	C33—C34	1.386 (3)
C9—O8	1.364 (3)	C33—H33	0.9500
C9—C10	1.395 (3)	C34—O3	1.397 (3)
C10—C11	1.389 (3)	C35—C36	1.380 (3)
C10—H10	0.9500	C35—C40	1.388 (3)
C11—C12	1.411 (3)	C35—O5	1.401 (2)
C11—C19	1.544 (3)	C36—C37	1.394 (3)
C12—O4	1.409 (2)	C36—H36	0.9500
C13—C16	1.533 (3)	C37—C38	1.390 (4)
C13—C14	1.536 (3)	C37—H37	0.9500
C13—C15	1.540 (3)	C38—C39	1.379 (3)
C14—H14A	0.9800	C38—H38	0.9500
C14—H14B	0.9800	C39—C40	1.406 (3)
C14—H14C	0.9800	C39—H39	0.9500
C15—H15A	0.9800	C40—C41	1.482 (3)
C15—H15B	0.9800	C41—C42	1.391 (3)
C15—H15C	0.9800	C41—C46	1.399 (3)
C16—H16A	0.9800	C42—C43	1.381 (3)
C16—H16B	0.9800	C42—H42	0.9500
C16—H16C	0.9800	C43—C44	1.386 (3)
C17—O7	1.420 (3)	C43—H43	0.9500
C17—H17A	0.9800	C44—C45	1.379 (3)
C17—H17B	0.9800	C44—H44	0.9500
C17—H17C	0.9800	C45—C46	1.384 (3)
C18—O8	1.428 (3)	C45—H45	0.9500
C18—H18A	0.9800	C46—O6	1.394 (3)
C18—H18B	0.9800	C47—C52	1.370 (4)
C18—H18C	0.9800	C47—C48	1.376 (4)
C19—C22	1.532 (3)	C47—H47	0.9500
C19—C21	1.539 (3)	C48—C49	1.377 (4)
C19—C20	1.543 (3)	C48—H48	0.9500
C20—H20A	0.9800	C49—C50	1.379 (5)
C20—H20B	0.9800	C49—H49	0.9500
C20—H20C	0.9800	C50—C51	1.386 (5)
C21—H21A	0.9800	C50—H50	0.9500
C21—H21B	0.9800	C51—C52	1.372 (5)
C21—H21C	0.9800	C51—H51	0.9500
C22—H22A	0.9800	C52—H52	0.9500
C22—H22B	0.9800	O1—P1	1.6372 (14)
C22—H22C	0.9800	O2—P1	1.6433 (14)
C23—C24	1.381 (3)	O3—P1	1.6300 (15)
C23—O2	1.392 (2)	O4—P2	1.6352 (13)
C23—C28	1.394 (3)	O5—P2	1.6419 (15)
C24—C25	1.394 (3)	O6—P2	1.6282 (15)
C24—H24	0.9500

C6—C1—C2	122.39 (18)	C23—C24—H24	120.4
C6—C1—O1	118.55 (17)	C25—C24—H24	120.4
C2—C1—O1	118.98 (18)	C26—C25—C24	119.8 (2)
C3—C2—C1	116.0 (2)	C26—C25—H25	120.1
C3—C2—C13	120.23 (19)	C24—C25—H25	120.1
C1—C2—C13	123.77 (19)	C25—C26—C27	120.5 (2)
C4—C3—C2	122.7 (2)	C25—C26—H26	119.7
C4—C3—H3	118.6	C27—C26—H26	119.7
C2—C3—H3	118.6	C26—C27—C28	121.0 (2)
O7—C4—C5	125.3 (2)	C26—C27—H27	119.5
O7—C4—C3	114.84 (19)	C28—C27—H27	119.5
C5—C4—C3	119.86 (19)	C23—C28—C27	117.2 (2)
C4—C5—C6	119.48 (19)	C23—C28—C29	121.77 (19)
C4—C5—H5	120.3	C27—C28—C29	121.0 (2)
C6—C5—H5	120.3	C34—C29—C30	117.2 (2)
C1—C6—C5	119.26 (18)	C34—C29—C28	121.9 (2)
C1—C6—C7	123.42 (18)	C30—C29—C28	120.9 (2)
C5—C6—C7	117.31 (18)	C31—C30—C29	121.6 (2)
C8—C7—C12	119.64 (18)	C31—C30—H30	119.2
C8—C7—C6	117.78 (17)	C29—C30—H30	119.2
C12—C7—C6	122.49 (18)	C30—C31—C32	120.0 (2)
C9—C8—C7	119.79 (18)	C30—C31—H31	120.0
C9—C8—H8	120.1	C32—C31—H31	120.0
C7—C8—H8	120.1	C31—C32—C33	119.8 (2)
O8—C9—C8	124.69 (19)	C31—C32—H32	120.1
O8—C9—C10	115.65 (18)	C33—C32—H32	120.1
C8—C9—C10	119.66 (19)	C34—C33—C32	119.4 (2)
C11—C10—C9	122.54 (19)	C34—C33—H33	120.3
C11—C10—H10	118.7	C32—C33—H33	120.3
C9—C10—H10	118.7	C33—C34—C29	121.8 (2)
C10—C11—C12	116.61 (18)	C33—C34—O3	117.58 (19)
C10—C11—C19	119.47 (18)	C29—C34—O3	120.5 (2)
C12—C11—C19	123.90 (18)	C36—C35—C40	122.08 (19)
C7—C12—O4	118.00 (17)	C36—C35—O5	119.21 (19)
C7—C12—C11	121.21 (19)	C40—C35—O5	118.60 (18)
O4—C12—C11	120.78 (17)	C35—C36—C37	119.5 (2)
C16—C13—C2	111.91 (19)	C35—C36—H36	120.2
C16—C13—C14	106.5 (2)	C37—C36—H36	120.2
C2—C13—C14	109.85 (18)	C38—C37—C36	119.5 (2)
C16—C13—C15	107.6 (2)	C38—C37—H37	120.3
C2—C13—C15	109.0 (2)	C36—C37—H37	120.3
C14—C13—C15	112.01 (19)	C39—C38—C37	120.5 (2)
C13—C14—H14A	109.5	C39—C38—H38	119.8
C13—C14—H14B	109.5	C37—C38—H38	119.8
H14A—C14—H14B	109.5	C38—C39—C40	120.9 (2)
C13—C14—H14C	109.5	C38—C39—H39	119.5
H14A—C14—H14C	109.5	C40—C39—H39	119.5
H14B—C14—H14C	109.5	C35—C40—C39	117.6 (2)
C13—C15—H15A	109.5	C35—C40—C41	121.36 (18)
C13—C15—H15B	109.5	C39—C40—C41	121.0 (2)
H15A—C15—H15B	109.5	C42—C41—C46	117.6 (2)
C13—C15—H15C	109.5	C42—C41—C40	120.90 (19)
H15A—C15—H15C	109.5	C46—C41—C40	121.5 (2)
H15B—C15—H15C	109.5	C43—C42—C41	121.4 (2)
C13—C16—H16A	109.5	C43—C42—H42	119.3
C13—C16—H16B	109.5	C41—C42—H42	119.3
H16A—C16—H16B	109.5	C42—C43—C44	119.8 (2)
C13—C16—H16C	109.5	C42—C43—H43	120.1
H16A—C16—H16C	109.5	C44—C43—H43	120.1
H16B—C16—H16C	109.5	C45—C44—C43	120.2 (2)
O7—C17—H17A	109.5	C45—C44—H44	119.9
O7—C17—H17B	109.5	C43—C44—H44	119.9
H17A—C17—H17B	109.5	C44—C45—C46	119.6 (2)
O7—C17—H17C	109.5	C44—C45—H45	120.2
H17A—C17—H17C	109.5	C46—C45—H45	120.2
H17B—C17—H17C	109.5	C45—C46—O6	118.40 (19)
O8—C18—H18A	109.5	C45—C46—C41	121.4 (2)
O8—C18—H18B	109.5	O6—C46—C41	119.96 (18)
H18A—C18—H18B	109.5	C52—C47—C48	120.5 (3)
O8—C18—H18C	109.5	C52—C47—H47	119.7
H18A—C18—H18C	109.5	C48—C47—H47	119.7
H18B—C18—H18C	109.5	C47—C48—C49	120.1 (3)
C22—C19—C21	106.76 (17)	C47—C48—H48	119.9
C22—C19—C20	110.18 (17)	C49—C48—H48	119.9
C21—C19—C20	107.29 (17)	C48—C49—C50	119.6 (3)
C22—C19—C11	111.34 (16)	C48—C49—H49	120.2
C21—C19—C11	111.70 (17)	C50—C49—H49	120.2
C20—C19—C11	109.46 (16)	C49—C50—C51	119.9 (3)
C19—C20—H20A	109.5	C49—C50—H50	120.1
C19—C20—H20B	109.5	C51—C50—H50	120.1
H20A—C20—H20B	109.5	C52—C51—C50	120.2 (3)
C19—C20—H20C	109.5	C52—C51—H51	119.9
H20A—C20—H20C	109.5	C50—C51—H51	119.9
H20B—C20—H20C	109.5	C47—C52—C51	119.7 (3)
C19—C21—H21A	109.5	C47—C52—H52	120.2
C19—C21—H21B	109.5	C51—C52—H52	120.2
H21A—C21—H21B	109.5	C1—O1—P1	120.65 (13)
C19—C21—H21C	109.5	C23—O2—P1	119.44 (12)
H21A—C21—H21C	109.5	C34—O3—P1	125.54 (12)
H21B—C21—H21C	109.5	C12—O4—P2	116.93 (12)
C19—C22—H22A	109.5	C35—O5—P2	115.87 (12)
C19—C22—H22B	109.5	C46—O6—P2	125.57 (12)
H22A—C22—H22B	109.5	C4—O7—C17	116.87 (18)
C19—C22—H22C	109.5	C9—O8—C18	115.57 (17)
H22A—C22—H22C	109.5	O3—P1—O1	102.27 (8)
H22B—C22—H22C	109.5	O3—P1—O2	99.42 (8)
C24—C23—O2	118.85 (19)	O1—P1—O2	93.84 (7)
C24—C23—C28	122.4 (2)	O6—P2—O4	102.43 (8)
O2—C23—C28	118.5 (2)	O6—P2—O5	99.14 (8)
C23—C24—C25	119.1 (2)	O4—P2—O5	95.73 (7)

C6—C1—C2—C3	4.9 (3)	C31—C32—C33—C34	−1.3 (3)
O1—C1—C2—C3	−178.35 (17)	C32—C33—C34—C29	3.6 (3)
C6—C1—C2—C13	−174.64 (19)	C32—C33—C34—O3	179.15 (17)
O1—C1—C2—C13	2.1 (3)	C30—C29—C34—C33	−3.1 (3)
C1—C2—C3—C4	−0.3 (3)	C28—C29—C34—C33	176.17 (18)
C13—C2—C3—C4	179.2 (2)	C30—C29—C34—O3	−178.52 (16)
C2—C3—C4—O7	178.8 (2)	C28—C29—C34—O3	0.8 (3)
C2—C3—C4—C5	−3.3 (3)	C40—C35—C36—C37	−0.5 (3)
O7—C4—C5—C6	−179.9 (2)	O5—C35—C36—C37	175.6 (2)
C3—C4—C5—C6	2.5 (3)	C35—C36—C37—C38	−0.2 (4)
C2—C1—C6—C5	−5.7 (3)	C36—C37—C38—C39	0.6 (4)
O1—C1—C6—C5	177.48 (17)	C37—C38—C39—C40	−0.5 (3)
C2—C1—C6—C7	175.04 (18)	C36—C35—C40—C39	0.6 (3)
O1—C1—C6—C7	−1.7 (3)	O5—C35—C40—C39	−175.47 (17)
C4—C5—C6—C1	1.9 (3)	C36—C35—C40—C41	178.2 (2)
C4—C5—C6—C7	−178.85 (18)	O5—C35—C40—C41	2.1 (3)
C1—C6—C7—C8	117.3 (2)	C38—C39—C40—C35	−0.1 (3)
C5—C6—C7—C8	−61.9 (2)	C38—C39—C40—C41	−177.74 (19)
C1—C6—C7—C12	−66.1 (3)	C35—C40—C41—C42	−136.9 (2)
C5—C6—C7—C12	114.7 (2)	C39—C40—C41—C42	40.6 (3)
C12—C7—C8—C9	1.6 (3)	C35—C40—C41—C46	42.9 (3)
C6—C7—C8—C9	178.23 (17)	C39—C40—C41—C46	−139.6 (2)
C7—C8—C9—O8	−175.82 (17)	C46—C41—C42—C43	−0.9 (3)
C7—C8—C9—C10	4.7 (3)	C40—C41—C42—C43	178.84 (18)
O8—C9—C10—C11	174.68 (17)	C41—C42—C43—C44	−0.1 (3)
C8—C9—C10—C11	−5.8 (3)	C42—C43—C44—C45	1.4 (3)
C9—C10—C11—C12	0.4 (3)	C43—C44—C45—C46	−1.7 (3)
C9—C10—C11—C19	−177.90 (17)	C44—C45—C46—O6	175.18 (17)
C8—C7—C12—O4	173.19 (16)	C44—C45—C46—C41	0.6 (3)
C6—C7—C12—O4	−3.3 (3)	C42—C41—C46—C45	0.6 (3)
C8—C7—C12—C11	−7.1 (3)	C40—C41—C46—C45	−179.11 (17)
C6—C7—C12—C11	176.38 (17)	C42—C41—C46—O6	−173.83 (16)
C10—C11—C12—C7	6.0 (3)	C40—C41—C46—O6	6.4 (3)
C19—C11—C12—C7	−175.73 (17)	C52—C47—C48—C49	−0.5 (4)
C10—C11—C12—O4	−174.29 (16)	C47—C48—C49—C50	−0.1 (4)
C19—C11—C12—O4	3.9 (3)	C48—C49—C50—C51	0.5 (4)
C3—C2—C13—C16	−8.9 (3)	C49—C50—C51—C52	−0.5 (4)
C1—C2—C13—C16	170.6 (2)	C48—C47—C52—C51	0.6 (4)
C3—C2—C13—C14	−126.9 (2)	C50—C51—C52—C47	−0.1 (4)
C1—C2—C13—C14	52.6 (3)	C6—C1—O1—P1	−63.9 (2)
C3—C2—C13—C15	110.0 (2)	C2—C1—O1—P1	119.26 (17)
C1—C2—C13—C15	−70.5 (3)	C24—C23—O2—P1	105.80 (19)
C10—C11—C19—C22	−133.04 (19)	C28—C23—O2—P1	−79.4 (2)
C12—C11—C19—C22	48.8 (2)	C33—C34—O3—P1	116.70 (17)
C10—C11—C19—C21	−13.8 (2)	C29—C34—O3—P1	−67.7 (2)
C12—C11—C19—C21	168.04 (18)	C7—C12—O4—P2	−66.19 (19)
C10—C11—C19—C20	104.9 (2)	C11—C12—O4—P2	114.13 (17)
C12—C11—C19—C20	−73.3 (2)	C36—C35—O5—P2	102.7 (2)
O2—C23—C24—C25	175.12 (19)	C40—C35—O5—P2	−81.1 (2)
C28—C23—C24—C25	0.5 (3)	C45—C46—O6—P2	116.01 (18)
C23—C24—C25—C26	−0.5 (3)	C41—C46—O6—P2	−69.4 (2)
C24—C25—C26—C27	−0.1 (4)	C5—C4—O7—C17	−1.9 (3)
C25—C26—C27—C28	0.6 (3)	C3—C4—O7—C17	175.8 (2)
C24—C23—C28—C27	0.0 (3)	C8—C9—O8—C18	14.4 (3)
O2—C23—C28—C27	−174.62 (17)	C10—C9—O8—C18	−166.10 (17)
C24—C23—C28—C29	178.94 (19)	C34—O3—P1—O1	−59.05 (17)
O2—C23—C28—C29	4.3 (3)	C34—O3—P1—O2	37.00 (17)
C26—C27—C28—C23	−0.6 (3)	C1—O1—P1—O3	−134.20 (14)
C26—C27—C28—C29	−179.5 (2)	C1—O1—P1—O2	125.29 (14)
C23—C28—C29—C34	43.9 (3)	C23—O2—P1—O3	53.57 (17)
C27—C28—C29—C34	−137.1 (2)	C23—O2—P1—O1	156.69 (16)
C23—C28—C29—C30	−136.8 (2)	C46—O6—P2—O4	−66.92 (16)
C27—C28—C29—C30	42.1 (3)	C46—O6—P2—O5	31.07 (17)
C34—C29—C30—C31	0.4 (3)	C12—O4—P2—O6	−131.10 (13)
C28—C29—C30—C31	−178.94 (19)	C12—O4—P2—O5	128.21 (13)
C29—C30—C31—C32	1.9 (3)	C35—O5—P2—O6	60.03 (15)
C30—C31—C32—C33	−1.4 (3)	C35—O5—P2—O4	163.63 (14)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C47–C52 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C39—H39···Cg1ⁱ	0.95	2.75	3.678 (3)	165

Symmetry code: (i) x, y−1, z.

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6,6′-[(3,3′-Di-tert-butyl-5,5′-dimeth­oxy-1,1′-biphenyl-2,2′-di­yl)bis(oxy)]bis­(dibenzo[d,f][1,3,2]dioxaphosphepine) benzene monosolvate

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6,6′-[(3,3′-Di-tert-butyl-5,5′-dimethoxy-1,1′-biphenyl-2,2′-diyl)bis(oxy)]bis(dibenzo[d,f][1,3,2]dioxaphosphepine) benzene monosolvate