1,4-Bis{5-[bis­(propan-2-yl­oxy)phosphor­yl]thio­phen-2-yl}-2,5-di­propoxybenzene

The title compound, C₃₂H₄₈O₈P₂S₂, was prepared by the nickel-catalyzed reaction of bis­(5-bromo­thien­yl)dipropoxybenzene and triisopropyl phosphite. The thio­phene rings are inclined to the benzene ring by 14.6 (2) and 25.3 (3)°. One prop­yloxy group is disordered. Four hydrogen bonds connect the mol­ecules, which are arranged in ribbons parallel to the bc plane.

Key indicators

• Single-crystal X-ray study
• T = 248 K
• Mean [sigma](C-C) = 0.011 Å
• Disorder in main residue
• R factor = 0.091
• wR factor = 0.304
• Data-to-parameter ratio = 20.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections (too) Low ..         38 %
PLAT242_ALERT_2_B Low    'MainMol' Ueq as Compared to Neighbors of        C41 Check
PLAT340_ALERT_3_B Low Bond Precision on  C-C Bonds ...............    0.01126 Ang.
PLAT910_ALERT_3_B Missing # of FCF Reflection(s) Below Theta(Min)          15 Note

Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.12
            Rint given   0.143
PLAT020_ALERT_3_C The value of Rint is greater than 0.12 .........      0.143 Report
PLAT084_ALERT_3_C High wR2 Value (i.e. > 0.25) ...................       0.30 Report
PLAT220_ALERT_2_C Non-Solvent Resd 1   C   Ueq(max)/Ueq(min) Range        5.4 Ratio
PLAT222_ALERT_3_C Non-Solvent Resd 1   H Uiso(max)/Uiso(min) Range        6.2 Ratio
PLAT234_ALERT_4_C Large Hirshfeld Difference C37    --  C38     ..       0.25 Ang.
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C22 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C26 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C37 Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8A    ..  O29     ..       2.61 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......     11.480 Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      3.188 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          9 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Note

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          5 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          6 Report
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.15 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          2 Report
PLAT300_ALERT_4_G Atom Site Occupancy of *C28    is Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *C28A   is Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *H26    is Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *H26A   is Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *H28A   is Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *H28B   is Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *H28C   is Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *H28D   is Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *H28E   is Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *H28F   is Constrained at        0.5 Check
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1)..          7 % Note
PLAT395_ALERT_2_G Deviating  X-O-Y   Angle from 120 Deg for  O21         123.4 Degre
PLAT395_ALERT_2_G Deviating  X-O-Y   Angle from 120 Deg for  O25         122.5 Degre
PLAT395_ALERT_2_G Deviating  X-O-Y   Angle from 120 Deg for  O36         122.8 Degre
PLAT395_ALERT_2_G Deviating  X-O-Y   Angle from 120 Deg for  O40         121.2 Degre
PLAT721_ALERT_1_G Bond    Calc     0.96000, Rep     0.97000 Dev...       0.01 Ang.
              C14A   -H14E          1.555   1.555 ............     #   40 Check
PLAT721_ALERT_1_G Bond    Calc     0.96000, Rep     0.97000 Dev...       0.01 Ang.
              C28    -H28A          1.555   1.555 ............     #   72 Check
PLAT793_ALERT_4_G The Model has Chirality at P20     (Centro SPGR)          S Verify
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         22 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          2 Note

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

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

---

Computing details

Data collection: X-AREA (Stoe & Cie, (1996); cell refinement: X-AREA (Stoe & Cie, (1996); data reduction: X-RED (Stoe & Cie, (1996); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

1,4-Bis{5-[bis(propan-2-yloxy)phosphoryl]thiophen-2-yl}-2,5-dipropoxybenzene

Crystal data

C32H48O8P2S2	Dx = 1.254 Mg m^−3
Mr = 686.76	Melting point: 458 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.6507 (8) Å	Cell parameters from 17095 reflections
b = 18.8828 (11) Å	θ = 3.3–28.7°
c = 14.5033 (8) Å	µ = 0.28 mm^−1
β = 103.279 (5)°	T = 248 K
V = 3638.5 (4) Å^3	Needle, yellow
Z = 4	0.40 × 0.15 × 0.08 mm
F(000) = 1464

Data collection

Stoe IPDS 2T diffractometer	3346 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.143
Detector resolution: 6.67 pixels mm^-1	θmax = 28.0°, θmin = 3.3°
rotation method scans	h = −18→18
25084 measured reflections	k = −24→24
8750 independent reflections	l = −18→19

Refinement

Refinement on F^2	22 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.091	H-atom parameters constrained
wR(F^2) = 0.304	w = 1/[σ^2(Fo^2) + (0.149P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.95	(Δ/σ)max < 0.001
8750 reflections	Δρmax = 0.73 e Å^−3
433 parameters	Δρmin = −0.53 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.7646 (4)	0.4573 (3)	0.1961 (4)	0.0391 (13)
C2	0.7995 (5)	0.4363 (3)	0.2908 (4)	0.0416 (14)
H2	0.8312	0.3921	0.3046	0.050*
C3	0.7876 (4)	0.4802 (3)	0.3644 (4)	0.0420 (14)
C4	0.7430 (4)	0.5466 (3)	0.3458 (4)	0.0390 (14)
C5	0.7098 (5)	0.5673 (3)	0.2520 (5)	0.0469 (15)
H5	0.6797	0.6120	0.2383	0.056*
C6	0.7200 (5)	0.5238 (3)	0.1788 (5)	0.0451 (15)
O7	0.8192 (4)	0.4617 (2)	0.4578 (3)	0.0522 (12)
C8	0.8661 (5)	0.3944 (3)	0.4836 (5)	0.0507 (16)
H8A	0.8313	0.3585	0.4391	0.061*
H8B	0.8578	0.3816	0.5469	0.061*
C9	0.9747 (5)	0.3929 (4)	0.4839 (6)	0.0610 (19)
H9A	1.0099	0.4297	0.5266	0.073*
H9B	0.9836	0.4031	0.4201	0.073*
C10	1.0204 (6)	0.3206 (5)	0.5163 (7)	0.077 (3)
H10A	1.0116	0.3106	0.5794	0.116*
H10B	1.0916	0.3210	0.5170	0.116*
H10C	0.9870	0.2844	0.4728	0.116*
O11	0.6883 (4)	0.5425 (3)	0.0852 (3)	0.0596 (13)
C12	0.6181 (7)	0.6006 (5)	0.0622 (5)	0.073 (2)
H12A	0.6526	0.6459	0.0788	0.087*	0.75 (2)
H12B	0.5647	0.5962	0.0970	0.087*	0.75 (2)
H12C	0.6481	0.6432	0.0955	0.087*	0.25 (2)
H12D	0.5571	0.5894	0.0842	0.087*	0.25 (2)
C13	0.5740 (17)	0.5964 (10)	−0.0441 (9)	0.101 (7)	0.75 (2)
H13A	0.5493	0.5484	−0.0616	0.121*	0.75 (2)
H13B	0.6259	0.6076	−0.0787	0.121*	0.75 (2)
C14	0.4868 (10)	0.6498 (9)	−0.0698 (12)	0.120 (7)	0.75 (2)
H14A	0.4578	0.6479	−0.1374	0.179*	0.75 (2)
H14B	0.4357	0.6381	−0.0356	0.179*	0.75 (2)
H14C	0.5121	0.6972	−0.0527	0.179*	0.75 (2)
C13A	0.590 (4)	0.615 (2)	−0.0446 (15)	0.057 (9)	0.25 (2)
H13C	0.6494	0.6148	−0.0711	0.068*	0.25 (2)
H13D	0.5565	0.6615	−0.0575	0.068*	0.25 (2)
C14A	0.517 (4)	0.555 (2)	−0.087 (2)	0.12 (2)	0.25 (2)
H14D	0.4960	0.5617	−0.1554	0.173*	0.25 (2)
H14E	0.5509	0.5101	−0.0736	0.173*	0.25 (2)
H14F	0.4585	0.5566	−0.0601	0.173*	0.25 (2)
C15	0.7770 (5)	0.4074 (3)	0.1201 (5)	0.0421 (14)
S16	0.78638 (15)	0.43527 (9)	0.00974 (12)	0.0519 (5)
C17	0.8043 (5)	0.3503 (4)	−0.0255 (5)	0.0456 (15)
C18	0.8015 (5)	0.3034 (4)	0.0459 (5)	0.0504 (16)
H18	0.8087	0.2542	0.0399	0.060*
C19	0.7871 (5)	0.3356 (3)	0.1282 (5)	0.0469 (15)
H19	0.7845	0.3104	0.1836	0.056*
P20	0.82830 (13)	0.33165 (9)	−0.13808 (12)	0.0447 (4)
O21	0.9359 (4)	0.3627 (3)	−0.1288 (4)	0.0601 (13)
C22	0.9893 (6)	0.3613 (5)	−0.2057 (6)	0.072 (2)
H22	0.9536	0.3291	−0.2563	0.087*
C23	1.0921 (7)	0.3323 (6)	−0.1643 (9)	0.106 (4)
H23A	1.1247	0.3609	−0.1104	0.159*
H23B	1.1318	0.3333	−0.2118	0.159*
H23C	1.0863	0.2839	−0.1438	0.159*
C24	0.9899 (8)	0.4339 (6)	−0.2448 (8)	0.105 (4)
H24A	0.9214	0.4484	−0.2730	0.158*
H24B	1.0292	0.4343	−0.2927	0.158*
H24C	1.0195	0.4664	−0.1943	0.158*
O25	0.7626 (3)	0.3838 (3)	−0.2104 (3)	0.0537 (12)
C26	0.6563 (6)	0.3737 (5)	−0.2468 (6)	0.072 (2)
H26	0.6280	0.3364	−0.2126	0.087*	0.5
H26A	0.6355	0.3462	−0.1964	0.087*	0.5
C27	0.6073 (11)	0.4452 (8)	−0.2428 (11)	0.154 (6)
H27A	0.6252	0.4765	−0.2894	0.230*
H27B	0.6306	0.4653	−0.1801	0.230*
H27C	0.5348	0.4395	−0.2565	0.230*
C28	0.640 (3)	0.358 (2)	−0.3540 (18)	0.121 (12)	0.5
H28A	0.5694	0.3511	−0.3814	0.182*	0.5
H28B	0.6646	0.3980	−0.3848	0.182*	0.5
H28C	0.6775	0.3159	−0.3630	0.182*	0.5
C28A	0.630 (2)	0.3329 (17)	−0.3222 (18)	0.086 (7)	0.5
H28D	0.5572	0.3297	−0.3407	0.130*	0.5
H28E	0.6552	0.3531	−0.3738	0.130*	0.5
H28F	0.6582	0.2860	−0.3076	0.130*	0.5
O29	0.8151 (4)	0.2567 (2)	−0.1632 (3)	0.0555 (12)
C30	0.7278 (4)	0.5954 (3)	0.4202 (4)	0.0397 (13)
S31	0.73883 (13)	0.57008 (9)	0.53735 (12)	0.0474 (4)
C32	0.7074 (4)	0.6532 (3)	0.5694 (4)	0.0403 (13)
C33	0.6920 (5)	0.6977 (4)	0.4946 (5)	0.0503 (16)
H33	0.6757	0.7458	0.4985	0.060*
C34	0.7026 (5)	0.6654 (4)	0.4104 (5)	0.0509 (16)
H34	0.6933	0.6897	0.3525	0.061*
P35	0.68713 (13)	0.67232 (9)	0.68365 (12)	0.0453 (4)
O36	0.7622 (4)	0.6266 (3)	0.7574 (4)	0.0626 (13)
C37	0.8578 (6)	0.6543 (5)	0.8129 (6)	0.073 (2)
H37	0.8513	0.7055	0.8254	0.088*
C38	0.8805 (9)	0.6139 (11)	0.9042 (9)	0.178 (8)
H38A	0.8315	0.6259	0.9407	0.267*
H38B	0.9474	0.6260	0.9402	0.267*
H38C	0.8774	0.5635	0.8909	0.267*
C39	0.9374 (8)	0.6428 (8)	0.7584 (10)	0.128 (5)
H39A	0.9446	0.5925	0.7483	0.192*
H39B	1.0009	0.6618	0.7939	0.192*
H39C	0.9182	0.6666	0.6976	0.192*
O40	0.5887 (3)	0.6316 (3)	0.6897 (4)	0.0566 (12)
C41	0.4946 (6)	0.6448 (5)	0.6224 (6)	0.074 (2)
H41	0.5103	0.6647	0.5643	0.089*
C42	0.4431 (8)	0.5766 (7)	0.5975 (10)	0.120 (4)
H42A	0.4884	0.5437	0.5772	0.181*
H42B	0.3840	0.5837	0.5466	0.181*
H42C	0.4229	0.5575	0.6524	0.181*
C43	0.4360 (11)	0.6990 (9)	0.6620 (15)	0.207 (10)
H43A	0.4116	0.6785	0.7138	0.310*
H43B	0.3793	0.7146	0.6128	0.310*
H43C	0.4789	0.7392	0.6851	0.310*
O44	0.6885 (4)	0.7489 (2)	0.6998 (4)	0.0593 (13)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.047 (3)	0.035 (3)	0.039 (3)	0.000 (3)	0.016 (3)	−0.002 (3)
C2	0.055 (4)	0.034 (3)	0.038 (3)	0.003 (3)	0.016 (3)	0.001 (3)
C3	0.049 (3)	0.041 (4)	0.040 (3)	−0.004 (3)	0.018 (3)	0.003 (3)
C4	0.046 (3)	0.033 (3)	0.041 (3)	0.002 (3)	0.018 (3)	0.000 (3)
C5	0.059 (4)	0.037 (4)	0.048 (4)	0.006 (3)	0.019 (3)	−0.001 (3)
C6	0.055 (4)	0.041 (4)	0.039 (3)	0.004 (3)	0.010 (3)	0.004 (3)
O7	0.077 (3)	0.039 (3)	0.043 (3)	0.016 (2)	0.019 (2)	0.001 (2)
C8	0.062 (4)	0.037 (4)	0.054 (4)	0.009 (3)	0.015 (3)	0.006 (3)
C9	0.055 (4)	0.059 (5)	0.071 (5)	0.001 (3)	0.019 (4)	0.000 (4)
C10	0.053 (4)	0.066 (6)	0.108 (8)	0.010 (4)	0.007 (5)	−0.007 (5)
O11	0.096 (4)	0.046 (3)	0.036 (2)	0.023 (3)	0.015 (2)	0.002 (2)
C12	0.105 (6)	0.058 (5)	0.049 (4)	0.033 (4)	0.004 (4)	−0.001 (4)
C13	0.155 (18)	0.061 (12)	0.072 (9)	0.018 (12)	−0.003 (9)	−0.001 (8)
C14	0.086 (10)	0.120 (14)	0.127 (14)	0.004 (8)	−0.028 (9)	0.051 (11)
C13A	0.07 (2)	0.051 (18)	0.044 (9)	0.019 (13)	0.006 (8)	−0.003 (8)
C14A	0.19 (4)	0.12 (3)	0.029 (12)	−0.07 (3)	0.008 (14)	0.010 (12)
C15	0.049 (3)	0.035 (3)	0.045 (4)	0.000 (3)	0.016 (3)	−0.003 (3)
S16	0.0842 (13)	0.0363 (9)	0.0418 (9)	0.0038 (8)	0.0284 (9)	0.0011 (7)
C17	0.047 (3)	0.044 (4)	0.049 (4)	0.000 (3)	0.018 (3)	−0.003 (3)
C18	0.063 (4)	0.040 (4)	0.052 (4)	0.004 (3)	0.021 (3)	−0.002 (3)
C19	0.066 (4)	0.040 (4)	0.040 (3)	0.004 (3)	0.023 (3)	0.001 (3)
P20	0.0555 (10)	0.0441 (10)	0.0386 (9)	0.0021 (8)	0.0190 (8)	−0.0022 (7)
O21	0.066 (3)	0.067 (3)	0.053 (3)	−0.006 (2)	0.026 (2)	−0.014 (3)
C22	0.078 (5)	0.083 (6)	0.068 (5)	−0.027 (5)	0.041 (4)	−0.020 (5)
C23	0.085 (7)	0.112 (9)	0.143 (10)	0.016 (6)	0.071 (7)	0.001 (7)
C24	0.120 (8)	0.106 (9)	0.101 (8)	−0.031 (7)	0.049 (7)	0.014 (7)
O25	0.065 (3)	0.058 (3)	0.040 (3)	0.008 (2)	0.015 (2)	0.006 (2)
C26	0.072 (5)	0.082 (6)	0.063 (5)	0.002 (4)	0.015 (4)	0.016 (4)
C27	0.149 (11)	0.142 (9)	0.151 (13)	0.062 (8)	−0.006 (9)	−0.022 (8)
C28	0.15 (2)	0.16 (3)	0.061 (16)	0.02 (2)	0.032 (16)	0.002 (17)
C28A	0.079 (13)	0.105 (13)	0.073 (11)	0.015 (11)	0.012 (10)	0.006 (10)
O29	0.081 (3)	0.045 (3)	0.045 (3)	0.000 (2)	0.023 (2)	−0.006 (2)
C30	0.044 (3)	0.041 (4)	0.035 (3)	0.002 (3)	0.013 (3)	−0.002 (3)
S31	0.0663 (10)	0.0374 (9)	0.0421 (9)	0.0044 (7)	0.0200 (8)	−0.0031 (7)
C32	0.048 (3)	0.038 (3)	0.036 (3)	0.001 (3)	0.011 (3)	−0.005 (3)
C33	0.065 (4)	0.036 (4)	0.054 (4)	0.006 (3)	0.024 (3)	−0.009 (3)
C34	0.065 (4)	0.042 (4)	0.051 (4)	0.009 (3)	0.022 (3)	0.002 (3)
P35	0.0516 (10)	0.0427 (10)	0.0433 (9)	0.0008 (7)	0.0145 (8)	−0.0068 (8)
O36	0.064 (3)	0.053 (3)	0.066 (3)	0.002 (2)	0.004 (3)	−0.002 (3)
C37	0.057 (4)	0.094 (7)	0.060 (5)	−0.008 (4)	−0.005 (4)	−0.002 (5)
C38	0.096 (9)	0.34 (2)	0.075 (8)	−0.011 (12)	−0.030 (7)	0.013 (12)
C39	0.069 (6)	0.163 (13)	0.159 (13)	0.008 (7)	0.039 (7)	0.007 (10)
O40	0.059 (3)	0.058 (3)	0.055 (3)	−0.004 (2)	0.019 (2)	−0.001 (2)
C41	0.060 (5)	0.096 (7)	0.067 (5)	−0.001 (4)	0.017 (4)	0.003 (5)
C42	0.079 (7)	0.144 (12)	0.127 (10)	−0.037 (7)	0.001 (6)	0.003 (8)
C43	0.111 (10)	0.207 (18)	0.29 (2)	0.079 (11)	0.014 (12)	−0.110 (16)
O44	0.085 (3)	0.039 (3)	0.060 (3)	−0.002 (2)	0.027 (3)	−0.010 (2)

Geometric parameters (Å, º)

C1—C6	1.393 (9)	C22—C23	1.498 (13)
C1—C2	1.404 (8)	C22—H22	0.9900
C1—C15	1.490 (8)	C23—H23A	0.9700
C2—C3	1.391 (8)	C23—H23B	0.9700
C2—H2	0.9400	C23—H23C	0.9700
C3—O7	1.369 (7)	C24—H24A	0.9700
C3—C4	1.394 (8)	C24—H24B	0.9700
C4—C5	1.386 (9)	C24—H24C	0.9700
C4—C30	1.470 (8)	O25—C26	1.437 (9)
C5—C6	1.374 (9)	C26—C28A	1.32 (3)
C5—H5	0.9400	C26—C27	1.513 (15)
C6—O11	1.373 (7)	C26—C28	1.55 (3)
O7—C8	1.433 (7)	C26—H26	0.9900
C8—C9	1.482 (9)	C26—H26A	0.9900
C8—H8A	0.9800	C27—H27A	0.9700
C8—H8B	0.9800	C27—H27B	0.9700
C9—C10	1.530 (11)	C27—H27C	0.9700
C9—H9A	0.9800	C28—H28A	0.9700
C9—H9B	0.9800	C28—H28B	0.9700
C10—H10A	0.9700	C28—H28C	0.9700
C10—H10B	0.9700	C28A—H28D	0.9700
C10—H10C	0.9700	C28A—H28E	0.9700
O11—C12	1.444 (8)	C28A—H28F	0.9700
C12—C13	1.523 (13)	C30—C34	1.363 (9)
C12—C13A	1.534 (19)	C30—S31	1.737 (6)
C12—H12A	0.9800	S31—C32	1.719 (6)
C12—H12B	0.9800	C32—C33	1.350 (9)
C12—H12C	0.9800	C32—P35	1.778 (6)
C12—H12D	0.9800	C33—C34	1.401 (9)
C13—C14	1.540 (17)	C33—H33	0.9400
C13—H13A	0.9800	C34—H34	0.9400
C13—H13B	0.9800	P35—O44	1.464 (5)
C14—H14A	0.9700	P35—O36	1.561 (5)
C14—H14B	0.9700	P35—O40	1.569 (5)
C14—H14C	0.9700	O36—C37	1.464 (9)
C13A—C14A	1.54 (2)	C37—C38	1.499 (16)
C13A—H13C	0.9800	C37—C39	1.499 (13)
C13A—H13D	0.9800	C37—H37	0.9900
C14A—H14D	0.9700	C38—H38A	0.9700
C14A—H14E	0.9700	C38—H38B	0.9700
C14A—H14F	0.9700	C38—H38C	0.9700
C15—C19	1.366 (9)	C39—H39A	0.9700
C15—S16	1.717 (6)	C39—H39B	0.9700
S16—C17	1.717 (7)	C39—H39C	0.9700
C17—C18	1.370 (9)	O40—C41	1.445 (10)
C17—P20	1.774 (6)	C41—C42	1.473 (14)
C18—C19	1.394 (9)	C41—C43	1.493 (14)
C18—H18	0.9400	C41—H41	0.9900
C19—H19	0.9400	C42—H42A	0.9700
P20—O29	1.461 (5)	C42—H42B	0.9700
P20—O21	1.558 (5)	C42—H42C	0.9700
P20—O25	1.562 (5)	C43—H43A	0.9700
O21—C22	1.465 (8)	C43—H43B	0.9700
C22—C24	1.484 (13)	C43—H43C	0.9700
C6—C1—C2	117.9 (6)	C22—C23—H23A	109.5
C6—C1—C15	123.8 (6)	C22—C23—H23B	109.5
C2—C1—C15	118.3 (5)	H23A—C23—H23B	109.5
C3—C2—C1	120.6 (6)	C22—C23—H23C	109.5
C3—C2—H2	119.7	H23A—C23—H23C	109.5
C1—C2—H2	119.7	H23B—C23—H23C	109.5
O7—C3—C2	122.8 (6)	C22—C24—H24A	109.5
O7—C3—C4	116.5 (5)	C22—C24—H24B	109.5
C2—C3—C4	120.7 (6)	H24A—C24—H24B	109.5
C5—C4—C3	118.2 (6)	C22—C24—H24C	109.5
C5—C4—C30	118.3 (5)	H24A—C24—H24C	109.5
C3—C4—C30	123.4 (6)	H24B—C24—H24C	109.5
C6—C5—C4	121.5 (6)	C26—O25—P20	122.6 (5)
C6—C5—H5	119.3	C28A—C26—O25	116.2 (14)
C4—C5—H5	119.3	C28A—C26—C27	120.9 (15)
O11—C6—C5	123.1 (6)	O25—C26—C27	106.6 (9)
O11—C6—C1	115.8 (5)	O25—C26—C28	106.9 (17)
C5—C6—C1	121.1 (6)	C27—C26—C28	104.2 (17)
C3—O7—C8	120.3 (5)	O25—C26—H26	112.9
O7—C8—C9	113.8 (6)	C27—C26—H26	112.9
O7—C8—H8A	108.8	C28—C26—H26	112.9
C9—C8—H8A	108.8	C28A—C26—H26A	103.6
O7—C8—H8B	108.8	O25—C26—H26A	103.6
C9—C8—H8B	108.8	C27—C26—H26A	103.6
H8A—C8—H8B	107.7	C26—C27—H27A	109.5
C8—C9—C10	110.8 (6)	C26—C27—H27B	109.5
C8—C9—H9A	109.5	H27A—C27—H27B	109.5
C10—C9—H9A	109.5	C26—C27—H27C	109.5
C8—C9—H9B	109.5	H27A—C27—H27C	109.5
C10—C9—H9B	109.5	H27B—C27—H27C	109.5
H9A—C9—H9B	108.1	C26—C28—H28A	109.5
C9—C10—H10A	109.5	C26—C28—H28B	109.5
C9—C10—H10B	109.5	H28A—C28—H28B	109.5
H10A—C10—H10B	109.5	C26—C28—H28C	109.5
C9—C10—H10C	109.5	H28A—C28—H28C	109.5
H10A—C10—H10C	109.5	H28B—C28—H28C	109.5
H10B—C10—H10C	109.5	C26—C28A—H28D	109.5
C6—O11—C12	117.7 (5)	C26—C28A—H28E	109.5
O11—C12—C13	106.3 (9)	H28D—C28A—H28E	109.5
O11—C12—C13A	112 (2)	C26—C28A—H28F	109.5
O11—C12—H12A	110.5	H28D—C28A—H28F	109.5
C13—C12—H12A	110.5	H28E—C28A—H28F	109.5
O11—C12—H12B	110.5	C34—C30—C4	127.2 (6)
C13—C12—H12B	110.5	C34—C30—S31	109.4 (5)
H12A—C12—H12B	108.7	C4—C30—S31	123.4 (5)
O11—C12—H12C	109.3	C32—S31—C30	92.4 (3)
C13A—C12—H12C	109.3	C33—C32—S31	110.6 (5)
O11—C12—H12D	109.3	C33—C32—P35	126.5 (5)
C13A—C12—H12D	109.3	S31—C32—P35	122.6 (4)
H12C—C12—H12D	107.9	C32—C33—C34	113.7 (6)
C12—C13—C14	108.3 (13)	C32—C33—H33	123.2
C12—C13—H13A	110.0	C34—C33—H33	123.2
C14—C13—H13A	110.0	C30—C34—C33	113.9 (6)
C12—C13—H13B	110.0	C30—C34—H34	123.1
C14—C13—H13B	110.0	C33—C34—H34	123.1
H13A—C13—H13B	108.4	O44—P35—O36	117.0 (3)
C13—C14—H14A	109.5	O44—P35—O40	117.0 (3)
C13—C14—H14B	109.5	O36—P35—O40	97.3 (3)
H14A—C14—H14B	109.5	O44—P35—C32	110.5 (3)
C13—C14—H14C	109.5	O36—P35—C32	107.9 (3)
H14A—C14—H14C	109.5	O40—P35—C32	105.7 (3)
H14B—C14—H14C	109.5	C37—O36—P35	122.7 (5)
C12—C13A—C14A	105 (3)	O36—C37—C38	106.3 (8)
C12—C13A—H13C	110.7	O36—C37—C39	108.7 (8)
C14A—C13A—H13C	110.7	C38—C37—C39	111.3 (10)
C12—C13A—H13D	110.7	O36—C37—H37	110.2
C14A—C13A—H13D	110.7	C38—C37—H37	110.2
H13C—C13A—H13D	108.8	C39—C37—H37	110.2
C13A—C14A—H14D	109.5	C37—C38—H38A	109.5
C13A—C14A—H14E	109.5	C37—C38—H38B	109.5
H14D—C14A—H14E	109.5	H38A—C38—H38B	109.5
C13A—C14A—H14F	109.5	C37—C38—H38C	109.5
H14D—C14A—H14F	109.5	H38A—C38—H38C	109.5
H14E—C14A—H14F	109.5	H38B—C38—H38C	109.5
C19—C15—C1	126.2 (6)	C37—C39—H39A	109.5
C19—C15—S16	111.0 (5)	C37—C39—H39B	109.5
C1—C15—S16	122.8 (5)	H39A—C39—H39B	109.5
C15—S16—C17	92.1 (3)	C37—C39—H39C	109.5
C18—C17—S16	110.5 (5)	H39A—C39—H39C	109.5
C18—C17—P20	127.6 (5)	H39B—C39—H39C	109.5
S16—C17—P20	121.9 (4)	C41—O40—P35	121.1 (5)
C17—C18—C19	113.5 (6)	O40—C41—C42	108.3 (8)
C17—C18—H18	123.3	O40—C41—C43	109.3 (9)
C19—C18—H18	123.3	C42—C41—C43	115.2 (10)
C15—C19—C18	113.0 (6)	O40—C41—H41	107.9
C15—C19—H19	123.5	C42—C41—H41	107.9
C18—C19—H19	123.5	C43—C41—H41	107.9
O29—P20—O21	116.4 (3)	C41—C42—H42A	109.5
O29—P20—O25	115.0 (3)	C41—C42—H42B	109.5
O21—P20—O25	101.9 (3)	H42A—C42—H42B	109.5
O29—P20—C17	112.6 (3)	C41—C42—H42C	109.5
O21—P20—C17	102.5 (3)	H42A—C42—H42C	109.5
O25—P20—C17	107.1 (3)	H42B—C42—H42C	109.5
C22—O21—P20	123.5 (5)	C41—C43—H43A	109.5
O21—C22—C24	108.8 (7)	C41—C43—H43B	109.5
O21—C22—C23	106.6 (8)	H43A—C43—H43B	109.5
C24—C22—C23	113.8 (8)	C41—C43—H43C	109.5
O21—C22—H22	109.2	H43A—C43—H43C	109.5
C24—C22—H22	109.2	H43B—C43—H43C	109.5
C23—C22—H22	109.2
C6—C1—C2—C3	1.3 (9)	C18—C17—P20—O25	145.5 (6)
C15—C1—C2—C3	−178.4 (5)	S16—C17—P20—O25	−37.6 (5)
C1—C2—C3—O7	179.3 (5)	O29—P20—O21—C22	57.9 (7)
C1—C2—C3—C4	−1.6 (9)	O25—P20—O21—C22	−68.1 (6)
O7—C3—C4—C5	−179.9 (5)	C17—P20—O21—C22	−178.9 (6)
C2—C3—C4—C5	0.9 (9)	P20—O21—C22—C24	106.5 (8)
O7—C3—C4—C30	−1.1 (8)	P20—O21—C22—C23	−130.4 (7)
C2—C3—C4—C30	179.7 (6)	O29—P20—O25—C26	48.7 (6)
C3—C4—C5—C6	0.1 (9)	O21—P20—O25—C26	175.6 (6)
C30—C4—C5—C6	−178.8 (6)	C17—P20—O25—C26	−77.2 (6)
C4—C5—C6—O11	−179.8 (6)	P20—O25—C26—C28A	−86.8 (15)
C4—C5—C6—C1	−0.3 (10)	P20—O25—C26—C27	135.2 (8)
C2—C1—C6—O11	179.1 (6)	P20—O25—C26—C28	−113.9 (15)
C15—C1—C6—O11	−1.2 (9)	C5—C4—C30—C34	−14.3 (10)
C2—C1—C6—C5	−0.3 (9)	C3—C4—C30—C34	166.9 (6)
C15—C1—C6—C5	179.4 (6)	C5—C4—C30—S31	165.1 (5)
C2—C3—O7—C8	−0.7 (9)	C3—C4—C30—S31	−13.7 (8)
C4—C3—O7—C8	−179.9 (5)	C34—C30—S31—C32	1.0 (5)
C3—O7—C8—C9	82.2 (8)	C4—C30—S31—C32	−178.5 (5)
O7—C8—C9—C10	177.5 (6)	C30—S31—C32—C33	−1.5 (5)
C5—C6—O11—C12	−17.3 (10)	C30—S31—C32—P35	173.0 (4)
C1—C6—O11—C12	163.3 (7)	S31—C32—C33—C34	1.6 (8)
C6—O11—C12—C13	−164.4 (11)	P35—C32—C33—C34	−172.6 (5)
C6—O11—C12—C13A	−179.9 (18)	C4—C30—C34—C33	179.1 (6)
O11—C12—C13—C14	171.3 (13)	S31—C30—C34—C33	−0.3 (8)
O11—C12—C13A—C14A	75 (4)	C32—C33—C34—C30	−0.8 (9)
C6—C1—C15—C19	−156.2 (7)	C33—C32—P35—O44	−21.7 (7)
C2—C1—C15—C19	23.5 (9)	S31—C32—P35—O44	164.7 (4)
C6—C1—C15—S16	27.1 (8)	C33—C32—P35—O36	−150.8 (6)
C2—C1—C15—S16	−153.2 (5)	S31—C32—P35—O36	35.6 (5)
C19—C15—S16—C17	−0.2 (5)	C33—C32—P35—O40	105.9 (6)
C1—C15—S16—C17	177.0 (5)	S31—C32—P35—O40	−67.7 (4)
C15—S16—C17—C18	0.7 (5)	O44—P35—O36—C37	−27.5 (7)
C15—S16—C17—P20	−176.6 (4)	O40—P35—O36—C37	−153.0 (6)
S16—C17—C18—C19	−1.1 (8)	C32—P35—O36—C37	97.8 (6)
P20—C17—C18—C19	176.1 (5)	P35—O36—C37—C38	150.9 (9)
C1—C15—C19—C18	−177.5 (6)	P35—O36—C37—C39	−89.1 (9)
S16—C15—C19—C18	−0.4 (8)	O44—P35—O40—C41	65.1 (6)
C17—C18—C19—C15	1.0 (9)	O36—P35—O40—C41	−169.5 (6)
C18—C17—P20—O29	18.1 (7)	C32—P35—O40—C41	−58.5 (6)
S16—C17—P20—O29	−165.0 (4)	P35—O40—C41—C42	139.7 (7)
C18—C17—P20—O21	−107.7 (6)	P35—O40—C41—C43	−94.0 (11)
S16—C17—P20—O21	69.2 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O29^i	0.98	2.61	3.533 (9)	156
C12—H12C···O44^ii	0.98	2.52	3.480 (10)	166
C19—H19···O29^i	0.94	2.51	3.436 (8)	169
C34—H34···O44^ii	0.94	2.49	3.424 (8)	174

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+3/2, z−1/2.