9-Oxo-10-di­phenyl­phosphinoyl­anthracene

In the title anthra­quinone derivative, C₂₆H₁₉O₂P, the dihedral angle of the two benzene rings is 30.2 (1)°. The di­phenyl­phosphinoyl unit lies out of the plane of the tricyclic core.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.040
• wR factor = 0.083
• Data-to-parameter ratio = 11.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT301_ALERT_3_B Main Residue  Disorder .........................      29.00 Perc.

Alert level C
PLAT031_ALERT_4_C Refined Extinction Parameter within Range ......       2.60 Sigma
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT165_ALERT_3_C Nr. of Status R Flagged Non-Hydrogen Atoms .....         24
PLAT215_ALERT_3_C Disordered C24     has ADP max/min Ratio .......       3.40
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C18'
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C24
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C26'
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT432_ALERT_2_C Short Inter X...Y Contact  C17'   ..  C20'    ..       3.17 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  C22    ..  C25     ..       3.13 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       3.60 Deg.
              C15  -P1   -C15'    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       1.90 Deg.
              C21' -P1   -C21     1.555   1.555   1.555

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.01
           From the CIF: _reflns_number_total               3286
           Count of symmetry unique reflns         1776
           Completeness (_total/calc)            185.02%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1510
           Fraction of Friedel pairs measured     0.850
           Are heavy atom types Z>Si present          yes

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  13 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 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
   4 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

9-oxo-10-diphenylphosphinoylanthracene

Crystal data

C26H19O2P	Dx = 1.350 Mg m^−3
Mr = 394.38	Melting point: 194 K
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
a = 19.386 (6) Å	Cell parameters from 543 reflections
b = 5.5840 (15) Å	θ = 2.1–25.0°
c = 17.928 (5) Å	µ = 0.16 mm^−1
V = 1940.7 (10) Å^3	T = 293 K
Z = 4	Prism, yellow
F(000) = 824	0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3286 independent reflections
Radiation source: fine-focus sealed tube	2286 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −23→14
Tmin = 0.953, Tmax = 0.968	k = −6→6
7475 measured reflections	l = −21→18

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.040	w = 1/[σ^2(Fo^2) + (0.0329P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.083	(Δ/σ)max < 0.001
S = 0.95	Δρmax = 0.21 e Å^−3
3286 reflections	Δρmin = −0.25 e Å^−3
296 parameters	Extinction correction: SHELXL97, Fc^* = kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0013 (5)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983); 1510 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.16 (11)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
P1	0.39876 (4)	0.15460 (13)	0.18231 (5)	0.0339 (2)
O1	0.39270 (11)	−0.1029 (3)	0.20080 (10)	0.0420 (6)
O2	0.33889 (14)	−0.2418 (4)	0.39450 (14)	0.0717 (9)
C1	0.37694 (16)	0.3426 (5)	0.26452 (15)	0.0362 (8)
H1	0.3807	0.5127	0.2518	0.043*
C2	0.30395 (18)	0.2817 (6)	0.28423 (17)	0.0386 (8)
C3	0.2490 (2)	0.4186 (6)	0.25796 (19)	0.0583 (11)
H3	0.2573	0.5548	0.2295	0.070*
C4	0.1824 (2)	0.3522 (9)	0.2742 (2)	0.0803 (13)
H4	0.1459	0.4453	0.2573	0.096*
C5	0.1695 (2)	0.1494 (10)	0.3151 (2)	0.0788 (14)
H5	0.1242	0.1045	0.3251	0.095*
C6	0.2228 (2)	0.0129 (7)	0.3414 (2)	0.0562 (10)
H6	0.2138	−0.1258	0.3684	0.067*
C7	0.29056 (18)	0.0826 (6)	0.32745 (18)	0.0408 (8)
C8	0.34749 (19)	−0.0481 (6)	0.36434 (18)	0.0470 (9)
C9	0.41396 (18)	0.0818 (6)	0.36992 (17)	0.0441 (9)
C10	0.4616 (2)	0.0143 (8)	0.4242 (2)	0.0627 (11)
H10	0.4533	−0.1198	0.4536	0.075*
C11	0.5214 (3)	0.1462 (10)	0.4346 (3)	0.0828 (15)
H11	0.5530	0.1017	0.4710	0.099*
C12	0.5335 (2)	0.3432 (9)	0.3907 (2)	0.0788 (13)
H12	0.5735	0.4323	0.3974	0.095*
C13	0.4869 (2)	0.4097 (7)	0.3368 (2)	0.0576 (10)
H13	0.4957	0.5440	0.3076	0.069*
C14	0.42726 (18)	0.2802 (5)	0.32525 (15)	0.0382 (8)
C15	0.4838 (2)	0.2336 (9)	0.1512 (3)	0.0341 (8)	0.50
C16	0.4977 (3)	0.3935 (9)	0.0937 (3)	0.0443 (19)	0.50
H16A	0.4616	0.4700	0.0692	0.053*	0.50
C17	0.5654 (3)	0.4389 (10)	0.0727 (3)	0.055 (2)	0.50
H17A	0.5747	0.5458	0.0342	0.066*	0.50
C18	0.6194 (2)	0.3245 (12)	0.1093 (3)	0.048 (7)	0.50
H18A	0.6647	0.3549	0.0953	0.058*	0.50
C19	0.6056 (3)	0.1646 (11)	0.1668 (3)	0.063 (2)	0.50
H19A	0.6417	0.0880	0.1913	0.076*	0.50
C20	0.5378 (3)	0.1192 (9)	0.1878 (3)	0.0439 (19)	0.50
H20A	0.5285	0.0122	0.2262	0.053*	0.50
C15'	0.4867 (3)	0.2271 (10)	0.1565 (3)	0.0341 (8)	0.50
C16'	0.5083 (3)	0.4587 (8)	0.1403 (3)	0.0439 (19)	0.50
H16B	0.4777	0.5861	0.1453	0.053*	0.50
C17'	0.5756 (3)	0.4998 (10)	0.1168 (3)	0.060 (2)	0.50
H17B	0.5900	0.6548	0.1060	0.072*	0.50
C18'	0.6212 (3)	0.3094 (14)	0.1093 (3)	0.076 (9)	0.50
H18B	0.6662	0.3369	0.0936	0.091*	0.50
C19'	0.5996 (3)	0.0777 (11)	0.1255 (3)	0.063 (2)	0.50
H19B	0.6301	−0.0497	0.1205	0.076*	0.50
C20'	0.5323 (4)	0.0366 (8)	0.1490 (3)	0.045 (2)	0.50
H20B	0.5178	−0.1184	0.1598	0.054*	0.50
C21	0.3386 (3)	0.2443 (10)	0.1100 (3)	0.0343 (8)	0.50
C22	0.2984 (3)	0.0635 (8)	0.0791 (3)	0.037 (2)*	0.50
H22A	0.3025	−0.0927	0.0966	0.045*	0.50
C23	0.2523 (3)	0.1162 (11)	0.0221 (3)	0.054 (3)*	0.50
H23A	0.2255	−0.0048	0.0014	0.065*	0.50
C24	0.2463 (3)	0.3496 (12)	−0.0041 (3)	0.072 (9)	0.50
H24A	0.2154	0.3849	−0.0422	0.086*	0.50
C25	0.2865 (4)	0.5304 (9)	0.0269 (3)	0.042 (2)	0.50
H25A	0.2824	0.6866	0.0094	0.051*	0.50
C26	0.3326 (3)	0.4777 (9)	0.0839 (3)	0.043 (2)*	0.50
H26A	0.3594	0.5987	0.1046	0.052*	0.50
C21'	0.3418 (3)	0.2408 (10)	0.1092 (3)	0.0343 (8)	0.50
C22'	0.2798 (3)	0.1170 (9)	0.1044 (3)	0.0418 (18)	0.50
H22B	0.2699	−0.0044	0.1383	0.050*	0.50
C23'	0.2325 (2)	0.1745 (10)	0.0490 (3)	0.056 (2)	0.50
H23B	0.1910	0.0917	0.0458	0.067*	0.50
C24'	0.2472 (3)	0.3559 (11)	−0.0017 (3)	0.043 (7)	0.50
H24B	0.2156	0.3945	−0.0387	0.052*	0.50
C25'	0.3093 (3)	0.4797 (10)	0.0031 (3)	0.060 (3)	0.50
H25B	0.3191	0.6011	−0.0308	0.072*	0.50
C26'	0.3566 (3)	0.4222 (10)	0.0585 (3)	0.058 (2)	0.50
H26B	0.3981	0.5050	0.0617	0.070*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0414 (5)	0.0277 (4)	0.0326 (4)	−0.0017 (4)	0.0030 (5)	0.0003 (4)
O1	0.0560 (13)	0.0291 (11)	0.0407 (15)	−0.0014 (10)	0.0026 (11)	0.0010 (9)
O2	0.093 (2)	0.0436 (14)	0.0781 (19)	−0.0033 (15)	0.0160 (17)	0.0234 (14)
C1	0.049 (2)	0.0238 (17)	0.0361 (19)	−0.0015 (16)	0.0031 (16)	0.0040 (15)
C2	0.042 (2)	0.039 (2)	0.0355 (19)	0.0028 (17)	0.0065 (17)	−0.0082 (16)
C3	0.060 (3)	0.071 (3)	0.044 (2)	0.017 (2)	0.008 (2)	0.0048 (19)
C4	0.046 (3)	0.134 (4)	0.061 (3)	0.032 (3)	0.004 (2)	0.005 (3)
C5	0.046 (3)	0.136 (4)	0.055 (3)	−0.019 (3)	0.010 (2)	−0.009 (3)
C6	0.055 (3)	0.067 (3)	0.047 (2)	−0.015 (2)	0.008 (2)	−0.0122 (19)
C7	0.050 (2)	0.0382 (19)	0.0343 (18)	−0.0078 (18)	0.0080 (18)	−0.0103 (16)
C8	0.065 (3)	0.041 (2)	0.0353 (19)	0.002 (2)	0.017 (2)	0.0009 (17)
C9	0.057 (3)	0.046 (2)	0.0293 (17)	0.0094 (19)	0.0059 (18)	−0.0031 (15)
C10	0.076 (3)	0.075 (3)	0.037 (2)	0.021 (3)	−0.004 (2)	0.0033 (19)
C11	0.064 (3)	0.130 (5)	0.054 (3)	0.026 (4)	−0.023 (3)	−0.014 (3)
C12	0.057 (3)	0.115 (4)	0.064 (3)	−0.019 (3)	−0.007 (2)	−0.023 (3)
C13	0.058 (3)	0.065 (3)	0.049 (2)	−0.015 (2)	0.008 (2)	−0.0142 (19)
C14	0.046 (2)	0.0354 (19)	0.0330 (19)	0.0029 (16)	0.0025 (17)	−0.0039 (15)
C15	0.0418 (19)	0.0289 (19)	0.0317 (18)	−0.0007 (16)	0.0030 (16)	−0.0024 (13)
C16	0.045 (5)	0.041 (5)	0.047 (5)	0.008 (4)	0.004 (4)	0.008 (4)
C17	0.052 (5)	0.054 (5)	0.060 (6)	−0.001 (5)	0.020 (5)	0.003 (4)
C18	0.019 (9)	0.047 (11)	0.079 (19)	0.006 (9)	0.021 (10)	0.000 (12)
C19	0.034 (4)	0.069 (5)	0.088 (8)	0.010 (5)	−0.004 (5)	0.009 (5)
C20	0.044 (4)	0.040 (4)	0.048 (5)	0.001 (4)	0.003 (5)	0.016 (4)
C15'	0.0418 (19)	0.0289 (19)	0.0317 (18)	−0.0007 (16)	0.0030 (16)	−0.0024 (13)
C16'	0.042 (5)	0.035 (5)	0.054 (5)	0.002 (3)	0.006 (4)	−0.002 (4)
C17'	0.053 (6)	0.053 (5)	0.073 (6)	−0.015 (5)	0.003 (5)	0.000 (5)
C18'	0.084 (16)	0.087 (17)	0.056 (18)	−0.026 (14)	0.000 (13)	0.004 (14)
C19'	0.052 (6)	0.068 (6)	0.070 (6)	0.001 (5)	0.005 (5)	0.007 (5)
C20'	0.060 (6)	0.038 (5)	0.037 (5)	0.001 (4)	0.012 (4)	0.004 (3)
C21	0.042 (2)	0.0311 (18)	0.0298 (17)	−0.0044 (16)	0.0086 (16)	−0.0026 (14)
C24	0.072 (19)	0.089 (17)	0.054 (12)	0.010 (11)	−0.027 (11)	−0.052 (9)
C25	0.036 (5)	0.050 (5)	0.041 (5)	0.010 (4)	0.008 (4)	0.008 (4)
C21'	0.042 (2)	0.0311 (18)	0.0298 (17)	−0.0044 (16)	0.0086 (16)	−0.0026 (14)
C22'	0.042 (4)	0.024 (4)	0.060 (5)	0.014 (4)	0.010 (4)	0.009 (3)
C23'	0.045 (5)	0.043 (5)	0.080 (6)	0.009 (4)	−0.006 (5)	0.000 (5)
C24'	0.046 (14)	0.046 (12)	0.037 (10)	0.023 (8)	0.008 (9)	0.025 (7)
C25'	0.074 (8)	0.076 (7)	0.031 (5)	0.007 (6)	0.001 (5)	0.020 (5)
C26'	0.067 (6)	0.056 (5)	0.053 (5)	−0.016 (5)	−0.017 (5)	0.010 (4)

Geometric parameters (Å, º)

P1—O1	1.4803 (18)	C18—C19	1.390
P1—C21'	1.780 (4)	C18—H18A	0.930
P1—C15	1.796 (5)	C19—C20	1.390
P1—C15'	1.812 (5)	C19—H19A	0.930
P1—C21	1.814 (5)	C20—H20A	0.930
P1—C1	1.858 (3)	C15'—C16'	1.390
O2—C8	1.220 (4)	C15'—C20'	1.390
C1—C2	1.498 (4)	C16'—C17'	1.390
C1—C14	1.503 (4)	C16'—H16B	0.930
C1—H1	0.980	C17'—C18'	1.390
C2—C7	1.380 (4)	C17'—H17B	0.930
C2—C3	1.394 (4)	C18'—C19'	1.390
C3—C4	1.373 (5)	C18'—H18B	0.930
C3—H3	0.930	C19'—C20'	1.390
C4—C5	1.373 (6)	C19'—H19B	0.930
C4—H4	0.930	C20'—H20B	0.930
C5—C6	1.367 (5)	C21—C22	1.390
C5—H5	0.930	C21—C26	1.390
C6—C7	1.393 (5)	C22—C23	1.390
C6—H6	0.930	C22—H22A	0.930
C7—C8	1.479 (5)	C23—C24	1.390
C8—C9	1.482 (5)	C23—H23A	0.930
C9—C14	1.391 (4)	C24—C25	1.390
C9—C10	1.394 (5)	C24—H24A	0.930
C10—C11	1.385 (5)	C25—C26	1.390
C10—H10	0.930	C25—H25A	0.930
C11—C12	1.373 (6)	C26—H26A	0.930
C11—H11	0.930	C21'—C22'	1.390
C12—C13	1.374 (5)	C21'—C26'	1.390
C12—H12	0.930	C22'—C23'	1.390
C13—C14	1.379 (4)	C22'—H22B	0.930
C13—H13	0.930	C23'—C24'	1.390
C15—C16	1.390	C23'—H23B	0.930
C15—C20	1.390	C24'—C25'	1.390
C16—C17	1.390	C24'—H24B	0.930
C16—H16A	0.930	C25'—C26'	1.390
C17—C18	1.390	C25'—H25B	0.930
C17—H17A	0.930	C26'—H26B	0.930
O1—P1—C21'	112.2 (2)	C16—C17—C18	120.0
O1—P1—C15	112.4 (2)	C16—C17—H17A	120.0
C21'—P1—C15	105.9 (3)	C18—C17—H17A	120.0
O1—P1—C15'	110.4 (2)	C17—C18—C19	120.0
C21'—P1—C15'	109.5 (3)	C17—C18—H18A	120.0
C15—P1—C15'	3.6 (3)	C19—C18—H18A	120.0
O1—P1—C21	112.1 (2)	C20—C19—C18	120.0
C21'—P1—C21	1.9 (3)	C20—C19—H19A	120.0
C15—P1—C21	107.5 (3)	C18—C19—H19A	120.0
C15'—P1—C21	111.1 (3)	C19—C20—C15	120.0
O1—P1—C1	110.67 (12)	C19—C20—H20A	120.0
C21'—P1—C1	106.9 (2)	C15—C20—H20A	120.0
C15—P1—C1	108.47 (19)	C16'—C15'—C20'	120.0
C15'—P1—C1	106.90 (18)	C16'—C15'—P1	123.0 (4)
C21—P1—C1	105.3 (2)	C20'—C15'—P1	116.9 (3)
C2—C1—C14	112.9 (3)	C15'—C16'—C17'	120.0
C2—C1—P1	105.9 (2)	C15'—C16'—H16B	120.0
C14—C1—P1	107.2 (2)	C17'—C16'—H16B	120.0
C2—C1—H1	110.2	C18'—C17'—C16'	120.0
C14—C1—H1	110.2	C18'—C17'—H17B	120.0
P1—C1—H1	110.2	C16'—C17'—H17B	120.0
C7—C2—C3	119.2 (3)	C17'—C18'—C19'	120.0
C7—C2—C1	119.5 (3)	C17'—C18'—H18B	120.0
C3—C2—C1	121.2 (3)	C19'—C18'—H18B	120.0
C4—C3—C2	119.9 (4)	C20'—C19'—C18'	120.0
C4—C3—H3	120.0	C20'—C19'—H19B	120.0
C2—C3—H3	120.0	C18'—C19'—H19B	120.0
C5—C4—C3	120.5 (4)	C19'—C20'—C15'	120.0
C5—C4—H4	119.7	C19'—C20'—H20B	120.0
C3—C4—H4	119.7	C15'—C20'—H20B	120.0
C6—C5—C4	120.4 (4)	C22—C21—C26	120.0
C6—C5—H5	119.8	C22—C21—P1	116.4 (3)
C4—C5—H5	119.8	C26—C21—P1	123.6 (3)
C5—C6—C7	119.7 (4)	C21—C22—C23	120.0
C5—C6—H6	120.1	C21—C22—H22A	120.0
C7—C6—H6	120.1	C23—C22—H22A	120.0
C2—C7—C6	120.2 (4)	C24—C23—C22	120.0
C2—C7—C8	120.6 (3)	C24—C23—H23A	120.0
C6—C7—C8	119.1 (3)	C22—C23—H23A	120.0
O2—C8—C7	122.2 (3)	C23—C24—C25	120.0
O2—C8—C9	121.5 (3)	C23—C24—H24A	120.0
C7—C8—C9	115.9 (3)	C25—C24—H24A	120.0
C14—C9—C10	119.6 (4)	C26—C25—C24	120.0
C14—C9—C8	120.8 (3)	C26—C25—H25A	120.0
C10—C9—C8	119.4 (3)	C24—C25—H25A	120.0
C11—C10—C9	120.3 (4)	C25—C26—C21	120.0
C11—C10—H10	119.9	C25—C26—H26A	120.0
C9—C10—H10	119.9	C21—C26—H26A	120.0
C12—C11—C10	119.5 (4)	C22'—C21'—C26'	120.0
C12—C11—H11	120.3	C22'—C21'—P1	116.6 (3)
C10—C11—H11	120.3	C26'—C21'—P1	123.4 (3)
C11—C12—C13	120.5 (4)	C23'—C22'—C21'	120.0
C11—C12—H12	119.8	C23'—C22'—H22B	120.0
C13—C12—H12	119.8	C21'—C22'—H22B	120.0
C12—C13—C14	121.0 (4)	C22'—C23'—C24'	120.0
C12—C13—H13	119.5	C22'—C23'—H23B	120.0
C14—C13—H13	119.5	C24'—C23'—H23B	120.0
C13—C14—C9	119.1 (3)	C25'—C24'—C23'	120.0
C13—C14—C1	122.1 (3)	C25'—C24'—H24B	120.0
C9—C14—C1	118.8 (3)	C23'—C24'—H24B	120.0
C16—C15—C20	120.0	C26'—C25'—C24'	120.0
C16—C15—P1	124.4 (3)	C26'—C25'—H25B	120.0
C20—C15—P1	115.6 (3)	C24'—C25'—H25B	120.0
C17—C16—C15	120.0	C25'—C26'—C21'	120.0
C17—C16—H16A	120.0	C25'—C26'—H26B	120.0
C15—C16—H16A	120.0	C21'—C26'—H26B	120.0
O1—P1—C1—C2	−60.4 (2)	C15—C16—C17—C18	0.0
C21'—P1—C1—C2	62.1 (3)	C16—C17—C18—C19	0.0
C15—P1—C1—C2	175.9 (3)	C17—C18—C19—C20	0.0
C15'—P1—C1—C2	179.3 (3)	C18—C19—C20—C15	0.0
C21—P1—C1—C2	61.1 (3)	C16—C15—C20—C19	0.0
O1—P1—C1—C14	60.5 (2)	P1—C15—C20—C19	178.8 (4)
C21'—P1—C1—C14	−177.0 (3)	O1—P1—C15'—C16'	−176.3 (3)
C15—P1—C1—C14	−63.2 (3)	C21'—P1—C15'—C16'	59.6 (4)
C15'—P1—C1—C14	−59.8 (3)	C15—P1—C15'—C16'	60 (4)
C21—P1—C1—C14	−178.1 (3)	C21—P1—C15'—C16'	58.6 (4)
C14—C1—C2—C7	−34.1 (4)	C1—P1—C15'—C16'	−55.9 (3)
P1—C1—C2—C7	83.0 (3)	O1—P1—C15'—C20'	7.2 (3)
C14—C1—C2—C3	147.8 (3)	C21'—P1—C15'—C20'	−116.9 (3)
P1—C1—C2—C3	−95.1 (3)	C15—P1—C15'—C20'	−116 (5)
C7—C2—C3—C4	−1.1 (5)	C21—P1—C15'—C20'	−117.9 (3)
C1—C2—C3—C4	177.0 (3)	C1—P1—C15'—C20'	127.7 (3)
C2—C3—C4—C5	−1.1 (6)	C20'—C15'—C16'—C17'	0.0
C3—C4—C5—C6	1.1 (6)	P1—C15'—C16'—C17'	−176.3 (4)
C4—C5—C6—C7	1.0 (6)	C15'—C16'—C17'—C18'	0.0
C3—C2—C7—C6	3.2 (5)	C16'—C17'—C18'—C19'	0.0
C1—C2—C7—C6	−174.9 (3)	C17'—C18'—C19'—C20'	0.0
C3—C2—C7—C8	−172.0 (3)	C18'—C19'—C20'—C15'	0.0
C1—C2—C7—C8	9.9 (4)	C16'—C15'—C20'—C19'	0.0
C5—C6—C7—C2	−3.2 (5)	P1—C15'—C20'—C19'	176.6 (4)
C5—C6—C7—C8	172.1 (3)	O1—P1—C21—C22	−3.4 (3)
C2—C7—C8—O2	−170.0 (3)	C21'—P1—C21—C22	89 (11)
C6—C7—C8—O2	14.8 (5)	C15—P1—C21—C22	120.6 (3)
C2—C7—C8—C9	16.6 (4)	C15'—P1—C21—C22	120.7 (3)
C6—C7—C8—C9	−158.7 (3)	C1—P1—C21—C22	−123.9 (3)
O2—C8—C9—C14	168.8 (3)	O1—P1—C21—C26	178.3 (3)
C7—C8—C9—C14	−17.7 (4)	C21'—P1—C21—C26	−89 (11)
O2—C8—C9—C10	−15.7 (5)	C15—P1—C21—C26	−57.7 (4)
C7—C8—C9—C10	157.8 (3)	C15'—P1—C21—C26	−57.6 (4)
C14—C9—C10—C11	1.1 (5)	C1—P1—C21—C26	57.8 (3)
C8—C9—C10—C11	−174.5 (3)	C26—C21—C22—C23	0.0
C9—C10—C11—C12	−0.4 (6)	P1—C21—C22—C23	−178.4 (4)
C10—C11—C12—C13	0.0 (6)	C21—C22—C23—C24	0.0
C11—C12—C13—C14	−0.3 (6)	C22—C23—C24—C25	0.0
C12—C13—C14—C9	1.0 (5)	C23—C24—C25—C26	0.0
C12—C13—C14—C1	−177.3 (3)	C24—C25—C26—C21	0.0
C10—C9—C14—C13	−1.4 (4)	C22—C21—C26—C25	0.0
C8—C9—C14—C13	174.1 (3)	P1—C21—C26—C25	178.2 (4)
C10—C9—C14—C1	177.0 (3)	O1—P1—C21'—C22'	31.3 (4)
C8—C9—C14—C1	−7.6 (4)	C15—P1—C21'—C22'	154.3 (3)
C2—C1—C14—C13	−149.0 (3)	C15'—P1—C21'—C22'	154.3 (3)
P1—C1—C14—C13	94.7 (3)	C21—P1—C21'—C22'	−57 (10)
C2—C1—C14—C9	32.7 (4)	C1—P1—C21'—C22'	−90.2 (3)
P1—C1—C14—C9	−83.6 (3)	O1—P1—C21'—C26'	−149.0 (3)
O1—P1—C15—C16	140.7 (3)	C15—P1—C21'—C26'	−26.0 (4)
C21'—P1—C15—C16	17.8 (4)	C15'—P1—C21'—C26'	−25.9 (4)
C15'—P1—C15—C16	−162 (5)	C21—P1—C21'—C26'	123 (11)
C21—P1—C15—C16	16.8 (4)	C1—P1—C21'—C26'	89.5 (3)
C1—P1—C15—C16	−96.6 (3)	C26'—C21'—C22'—C23'	0.0
O1—P1—C15—C20	−38.1 (3)	P1—C21'—C22'—C23'	179.7 (4)
C21'—P1—C15—C20	−160.9 (3)	C21'—C22'—C23'—C24'	0.0
C15'—P1—C15—C20	20 (4)	C22'—C23'—C24'—C25'	0.0
C21—P1—C15—C20	−161.9 (3)	C23'—C24'—C25'—C26'	0.0
C1—P1—C15—C20	84.6 (3)	C24'—C25'—C26'—C21'	0.0
C20—C15—C16—C17	0.0	C22'—C21'—C26'—C25'	0.0
P1—C15—C16—C17	−178.7 (4)	P1—C21'—C26'—C25'	−179.7 (4)