Bis[1,3-bis­(diphenyl­phosphinoylimino)isoindolinato-κ³ O,N,O′]calcium(II)

Abstract

In the title compound, [Ca(C₃₂H₂₄N₃O₂P₂)₂], the 1,3-bis­(diphenyl­phosphinoylimino)isoindoline ligand adopts a tridentate coordination mode. The compound exhibits a distorted octa­hedral geometry. The Ca atom lies on a twofold rotation axis.

Related literature

For a related compound with similar octa­hedral geometry, see: Cole et al. (2006 ▶). For related literature, see: Shang (2007 ▶).

Experimental

Crystal data

• [Ca(C₃₂H₂₄N₃O₂P₂)₂]

• M _r = 1129.04

• Monoclinic,

• a = 26.351 (2) Å

• b = 12.4790 (11) Å

• c = 21.1997 (19) Å

• β = 126.1720 (10)°

• V = 5627.4 (9) ų

• Z = 4

• Mo Kα radiation

• μ = 0.28 mm⁻¹

• T = 293 (2) K

• 0.20 × 0.15 × 0.10 mm

Data collection

• Bruker SMART CCD diffractometer

• Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.837, T _max = 0.973

• 11452 measured reflections

• 4959 independent reflections

• 4175 reflections with I > 2σ(I)

• R _int = 0.019

Refinement

• R[F ² > 2σ(F ²)] = 0.050

• wR(F ²) = 0.135

• S = 1.04

• 4959 reflections

• 357 parameters

• H-atom parameters constrained

• Δρ_max = 0.40 e Å⁻³

• Δρ_min = −0.25 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 1999 ▶); software used to prepare material for publication: SHELXTL/PC.

Supplementary Material

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Selected geometric parameters (Å, °).

Ca1—O1	2.2581 (18)
Ca1—O2	2.2646 (18)
Ca1—N2	2.5513 (18)

O1—Ca1—O1i	81.34 (11)
O1—Ca1—O2	93.49 (8)
O1—Ca1—O2i	157.41 (7)
O2—Ca1—O2i	99.09 (11)
O1—Ca1—N2i	110.51 (6)
O2—Ca1—N2i	80.48 (6)
O1—Ca1—N2	80.81 (6)
O2—Ca1—N2	90.12 (6)
N2i—Ca1—N2	165.55 (9)

Symmetry code: (i) .

supplementary crystallographic information

Comment

The bis(N-diphenylphosphinato)-isoindoline-1,3-diimine ligand is a new type of tridentate ligand (Shang, 2007). There are six atoms coordinated to calcium ion, the four oxygen atoms are approximately in an equatorial plane with calcium(II), the mean deviation from the plane is 0.3218Å and the two nitrogen atoms are in axial positions [N2—Ca—N2ⁱ 165.55 (9)° (symmetry code ⁱ: -x, y, 1/2 - z)]. Because the calcium ion is coordinated via two oxygen of the tridentate ligand, two six-membered rings of O1—P1—N1—C13—N2—Ca1 and O2ⁱ—P2ⁱ—N3ⁱ—C20—N2—Ca1 are formed. The dihedral angles between the two six-membered rings and the isoindoline ring are 12.5° and 14.0° respectively. The Ca—O and Ca—N bond lengths of the compound are 2.2581 (18) [Ca1—O1], 2.2646 (18) [Ca1—O2] and 2.5513 (18) [Ca1—N2] Å, respectively. The values are comparable to the octahedral compound [Ca(o-TolForm)₂(thf)₂], which can provide four nitrogen and two oxygen atoms to coordinate calcium(II), the average bond length of Ca—O is 2.368 (2) and Ca—N is 2.43 (2)Å (Cole et al., 2006).

Experimental

The red crystal of bis(N-diphenylphosphinato)-isoindoline-1,3-diimine (Shang, 2007) (0.287 g, 0.53 mmol) was dissolved in absolute ethanol (20 ml), the calcium chloride (0.060 g, 0.53 mmol) was added to the solution in room temperature and the mixture was reacted for 24 h before getting the clear yellow solution, the solvent was evaporated slowly to give pink crystals of title compund. Yield: 0.14 g, 47%. Spectroscopic analysis, ¹H NMR (300 MHz, CDCl₃, δ): 7.73–7.88(m, 16H, phenyl; 4H, isoindoline); 7.51–7.54 (t, 4H, J=8.1, isoindoline); 7.10–7.27 (m, 24H, phenyl). ³¹P-{¹H} NMR (300 MHz, CDCl₃, δ): 20.2(s).

Refinement

H atoms were placed in their idealized positions and allowed to ride on the respective parent atoms with C—H 0.93 Å, and with U_iso(H) = 1.2U_eq (parent atom).

Figures

Fig. 1.

Molecular structure of I, showing the atom-labeling scheme and 20% probability displacement ellipsoids. Symmetry codes: (i) -x, y, -z + 1/2.

Crystal data

[Ca(C32H24N3O2P2)2]	F000 = 2344
Mr = 1129.04	Dx = 1.333 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4426 reflections
a = 26.351 (2) Å	θ = 2.4–25.9º
b = 12.4790 (11) Å	µ = 0.28 mm−1
c = 21.1997 (19) Å	T = 293 (2) K
β = 126.1720 (10)º	Block, pink
V = 5627.4 (9) Å3	0.20 × 0.15 × 0.10 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer	4959 independent reflections
Radiation source: fine-focus sealed tube	4175 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.019
T = 293(2) K	θmax = 25.0º
ω scan	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −31→17
Tmin = 0.837, Tmax = 0.973	k = −14→14
11452 measured reflections	l = −22→25

Refinement

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)] = 0.050	H-atom parameters constrained
wR(F2) = 0.135	w = 1/[σ2(Fo2) + (0.075P)2 + 4.1489P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
4959 reflections	Δρmax = 0.40 e Å−3
357 parameters	Δρmin = −0.25 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
Ca1	0.0000	0.39576 (5)	0.2500	0.03918 (18)
P1	0.12637 (3)	0.56655 (5)	0.33048 (4)	0.04665 (19)
P2	0.02345 (3)	0.23193 (6)	0.13903 (4)	0.0498 (2)
O1	0.06204 (8)	0.53300 (15)	0.26479 (10)	0.0621 (5)
O2	0.04545 (8)	0.27801 (16)	0.21607 (10)	0.0620 (5)
N1	0.16798 (9)	0.49240 (15)	0.40938 (11)	0.0447 (5)
N2	0.09048 (8)	0.37004 (14)	0.39391 (10)	0.0401 (4)
N3	−0.05179 (10)	0.22572 (18)	0.06938 (12)	0.0553 (6)
C1	0.17484 (14)	0.57710 (19)	0.29706 (17)	0.0566 (7)
C2	0.23898 (16)	0.5685 (3)	0.3464 (2)	0.0778 (9)
H2B	0.2592	0.5583	0.3996	0.093*
C3	0.2736 (2)	0.5750 (4)	0.3164 (4)	0.1129 (15)
H3B	0.3171	0.5684	0.3502	0.135*
C4	0.2464 (4)	0.5902 (4)	0.2414 (5)	0.137 (2)
H4A	0.2707	0.5947	0.2228	0.164*
C5	0.1831 (4)	0.5992 (4)	0.1915 (3)	0.1284 (19)
H5A	0.1641	0.6105	0.1386	0.154*
C6	0.1460 (2)	0.5919 (3)	0.2183 (2)	0.0868 (10)
H6A	0.1025	0.5970	0.1836	0.104*
C7	0.12490 (12)	0.6964 (2)	0.36669 (15)	0.0547 (6)
C8	0.07017 (16)	0.7308 (3)	0.3552 (2)	0.0752 (9)
H8A	0.0340	0.6891	0.3269	0.090*
C9	0.0699 (2)	0.8278 (4)	0.3864 (3)	0.1074 (14)
H9A	0.0330	0.8513	0.3784	0.129*
C10	0.1221 (2)	0.8895 (3)	0.4283 (3)	0.1118 (15)
H10A	0.1211	0.9539	0.4496	0.134*
C11	0.1762 (2)	0.8569 (3)	0.4391 (2)	0.0951 (12)
H11A	0.2120	0.8996	0.4672	0.114*
C12	0.17765 (14)	0.7608 (2)	0.40839 (18)	0.0681 (8)
H12A	0.2146	0.7390	0.4158	0.082*
C13	0.14975 (10)	0.41314 (16)	0.43053 (13)	0.0380 (5)
C14	0.19536 (10)	0.35340 (17)	0.50380 (12)	0.0391 (5)
C15	0.25946 (11)	0.36174 (19)	0.55869 (14)	0.0460 (5)
H15A	0.2823	0.4153	0.5553	0.055*
C16	0.28879 (12)	0.2881 (2)	0.61895 (14)	0.0513 (6)
H16A	0.3321	0.2919	0.6566	0.062*
C17	0.25463 (13)	0.2089 (2)	0.62393 (14)	0.0547 (6)
H17A	0.2752	0.1603	0.6651	0.066*
C18	0.19053 (12)	0.2007 (2)	0.56887 (14)	0.0508 (6)
H18A	0.1675	0.1473	0.5721	0.061*
C19	0.16168 (11)	0.27412 (18)	0.50904 (13)	0.0415 (5)
C20	0.09548 (11)	0.28795 (18)	0.44013 (13)	0.0426 (5)
C21	0.05040 (12)	0.0949 (2)	0.15292 (17)	0.0561 (7)
C22	0.05167 (16)	0.0416 (2)	0.0977 (2)	0.0803 (9)
H22A	0.0369	0.0756	0.0508	0.096*
C23	0.0743 (2)	−0.0612 (3)	0.1100 (3)	0.1070 (15)
H23A	0.0739	−0.0961	0.0710	0.128*
C24	0.0965 (2)	−0.1109 (4)	0.1762 (4)	0.136 (2)
H24A	0.1124	−0.1800	0.1842	0.163*
C25	0.0960 (2)	−0.0614 (4)	0.2325 (3)	0.127 (2)
H25A	0.1112	−0.0970	0.2790	0.152*
C26	0.07300 (17)	0.0426 (3)	0.2215 (2)	0.0937 (12)
H26A	0.0730	0.0764	0.2606	0.112*
C27	0.05800 (14)	0.2982 (2)	0.09748 (17)	0.0580 (7)
C28	0.12267 (17)	0.2995 (3)	0.1398 (2)	0.0836 (10)
H28A	0.1472	0.2687	0.1893	0.100*
C29	0.1514 (2)	0.3465 (4)	0.1089 (3)	0.1113 (14)
H29A	0.1949	0.3460	0.1374	0.134*
C30	0.1164 (3)	0.3927 (4)	0.0380 (3)	0.1186 (17)
H30A	0.1358	0.4242	0.0175	0.142*
C31	0.0531 (3)	0.3935 (4)	−0.0037 (3)	0.1218 (16)
H31A	0.0292	0.4266	−0.0523	0.146*
C32	0.0238 (2)	0.3460 (3)	0.0250 (2)	0.0955 (11)
H32A	−0.0199	0.3459	−0.0050	0.115*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
Ca1	0.0386 (4)	0.0401 (3)	0.0360 (3)	0.000	0.0204 (3)	0.000
P1	0.0463 (4)	0.0371 (3)	0.0518 (4)	−0.0034 (3)	0.0263 (3)	0.0065 (3)
P2	0.0419 (4)	0.0577 (4)	0.0489 (4)	0.0108 (3)	0.0264 (3)	−0.0027 (3)
O1	0.0561 (11)	0.0557 (11)	0.0553 (10)	−0.0095 (9)	0.0223 (9)	0.0121 (8)
O2	0.0436 (10)	0.0838 (13)	0.0508 (10)	0.0106 (9)	0.0235 (8)	−0.0090 (9)
N1	0.0411 (10)	0.0383 (10)	0.0520 (11)	−0.0033 (8)	0.0259 (9)	0.0042 (8)
N2	0.0379 (10)	0.0403 (10)	0.0422 (10)	−0.0024 (8)	0.0236 (9)	0.0005 (8)
N3	0.0466 (12)	0.0641 (13)	0.0494 (12)	0.0124 (10)	0.0252 (10)	−0.0099 (10)
C1	0.0760 (19)	0.0373 (12)	0.0700 (17)	−0.0044 (12)	0.0506 (15)	0.0060 (12)
C2	0.078 (2)	0.073 (2)	0.107 (3)	0.0026 (16)	0.068 (2)	0.0189 (18)
C3	0.115 (3)	0.099 (3)	0.179 (5)	0.010 (2)	0.117 (4)	0.033 (3)
C4	0.209 (6)	0.100 (3)	0.214 (7)	0.000 (4)	0.188 (6)	0.021 (4)
C5	0.230 (7)	0.102 (3)	0.125 (4)	−0.022 (4)	0.145 (5)	0.002 (3)
C6	0.123 (3)	0.073 (2)	0.079 (2)	−0.011 (2)	0.068 (2)	0.0041 (17)
C7	0.0567 (15)	0.0437 (13)	0.0543 (14)	0.0071 (12)	0.0276 (13)	0.0102 (11)
C8	0.0617 (19)	0.074 (2)	0.083 (2)	0.0110 (15)	0.0385 (17)	0.0006 (17)
C9	0.092 (3)	0.108 (3)	0.121 (3)	0.033 (3)	0.062 (3)	−0.007 (3)
C10	0.123 (4)	0.075 (2)	0.100 (3)	0.025 (3)	0.045 (3)	−0.020 (2)
C11	0.097 (3)	0.0507 (18)	0.093 (2)	0.0058 (18)	0.032 (2)	−0.0062 (17)
C12	0.0599 (17)	0.0423 (14)	0.0785 (19)	0.0003 (12)	0.0277 (15)	0.0001 (13)
C13	0.0405 (12)	0.0342 (11)	0.0434 (12)	−0.0013 (9)	0.0271 (10)	−0.0025 (9)
C14	0.0411 (12)	0.0358 (11)	0.0413 (12)	−0.0008 (9)	0.0247 (10)	−0.0031 (9)
C15	0.0409 (13)	0.0422 (12)	0.0499 (13)	−0.0036 (10)	0.0240 (11)	−0.0022 (10)
C16	0.0417 (13)	0.0513 (14)	0.0450 (13)	0.0003 (11)	0.0168 (11)	−0.0042 (11)
C17	0.0599 (16)	0.0496 (14)	0.0438 (13)	0.0060 (12)	0.0246 (13)	0.0061 (11)
C18	0.0520 (15)	0.0495 (13)	0.0479 (13)	−0.0043 (11)	0.0277 (12)	0.0077 (11)
C19	0.0439 (13)	0.0428 (12)	0.0404 (11)	−0.0031 (10)	0.0262 (10)	−0.0004 (10)
C20	0.0435 (13)	0.0458 (12)	0.0399 (12)	−0.0051 (10)	0.0254 (10)	0.0002 (10)
C21	0.0401 (14)	0.0548 (15)	0.0686 (17)	0.0039 (11)	0.0294 (13)	0.0092 (13)
C22	0.094 (2)	0.0589 (18)	0.116 (3)	0.0194 (17)	0.078 (2)	0.0013 (18)
C23	0.097 (3)	0.062 (2)	0.186 (5)	0.015 (2)	0.097 (3)	−0.006 (3)
C24	0.082 (3)	0.058 (2)	0.201 (6)	0.013 (2)	0.046 (4)	0.018 (3)
C25	0.122 (4)	0.066 (3)	0.110 (3)	−0.002 (2)	0.023 (3)	0.035 (2)
C26	0.093 (3)	0.075 (2)	0.077 (2)	−0.0154 (19)	0.030 (2)	0.0097 (18)
C27	0.0699 (18)	0.0457 (14)	0.0656 (16)	0.0075 (12)	0.0440 (15)	−0.0001 (12)
C28	0.075 (2)	0.091 (2)	0.089 (2)	−0.0115 (18)	0.0504 (19)	0.0041 (19)
C29	0.111 (3)	0.110 (3)	0.145 (4)	−0.030 (3)	0.093 (3)	−0.004 (3)
C30	0.185 (5)	0.087 (3)	0.144 (4)	−0.023 (3)	0.130 (4)	0.002 (3)
C31	0.161 (5)	0.121 (4)	0.110 (3)	0.015 (3)	0.095 (4)	0.040 (3)
C32	0.103 (3)	0.103 (3)	0.083 (2)	0.023 (2)	0.056 (2)	0.029 (2)

Geometric parameters (Å, °)

Ca1—O1	2.2581 (18)	C10—H10A	0.9300
Ca1—O1i	2.2581 (18)	C11—C12	1.376 (4)
Ca1—O2	2.2646 (18)	C11—H11A	0.9300
Ca1—O2i	2.2646 (18)	C12—H12A	0.9300
Ca1—N2i	2.5513 (18)	C13—C14	1.486 (3)
Ca1—N2	2.5513 (18)	C14—C19	1.377 (3)
Ca1—P2	3.4369 (8)	C14—C15	1.377 (3)
Ca1—P2i	3.4369 (8)	C15—C16	1.381 (3)
Ca1—P1	3.4403 (7)	C15—H15A	0.9300
Ca1—P1i	3.4403 (7)	C16—C17	1.382 (4)
P1—O1	1.4837 (18)	C16—H16A	0.9300
P1—N1	1.6406 (19)	C17—C18	1.378 (4)
P1—C1	1.794 (3)	C17—H17A	0.9300
P1—C7	1.803 (3)	C18—C19	1.374 (3)
P2—O2	1.4888 (19)	C18—H18A	0.9300
P2—N3	1.631 (2)	C19—C20	1.483 (3)
P2—C27	1.799 (3)	C20—N3i	1.302 (3)
P2—C21	1.808 (3)	C21—C22	1.363 (4)
N1—C13	1.290 (3)	C21—C26	1.367 (4)
N2—C20	1.369 (3)	C22—C23	1.373 (5)
N2—C13	1.378 (3)	C22—H22A	0.9300
N3—C20i	1.302 (3)	C23—C24	1.313 (7)
C1—C2	1.369 (4)	C23—H23A	0.9300
C1—C6	1.379 (4)	C24—C25	1.351 (8)
C2—C3	1.388 (5)	C24—H24A	0.9300
C2—H2B	0.9300	C25—C26	1.393 (6)
C3—C4	1.316 (8)	C25—H25A	0.9300
C3—H3B	0.9300	C26—H26A	0.9300
C4—C5	1.354 (7)	C27—C32	1.377 (4)
C4—H4A	0.9300	C27—C28	1.380 (4)
C5—C6	1.393 (6)	C28—C29	1.390 (5)
C5—H5A	0.9300	C28—H28A	0.9300
C6—H6A	0.9300	C29—C30	1.344 (7)
C7—C8	1.382 (4)	C29—H29A	0.9300
C7—C12	1.382 (4)	C30—C31	1.350 (7)
C8—C9	1.381 (5)	C30—H30A	0.9300
C8—H8A	0.9300	C31—C32	1.366 (6)
C9—C10	1.353 (6)	C31—H31A	0.9300
C9—H9A	0.9300	C32—H32A	0.9300
C10—C11	1.365 (6)
O1—Ca1—O1i	81.34 (11)	C4—C5—H5A	119.5
O1—Ca1—O2	93.49 (8)	C6—C5—H5A	119.5
O1i—Ca1—O2	157.41 (7)	C1—C6—C5	119.0 (4)
O1—Ca1—O2i	157.41 (7)	C1—C6—H6A	120.5
O1i—Ca1—O2i	93.49 (8)	C5—C6—H6A	120.5
O2—Ca1—O2i	99.09 (11)	C8—C7—C12	118.9 (3)
O1—Ca1—N2i	110.51 (6)	C8—C7—P1	119.1 (2)
O1i—Ca1—N2i	80.81 (6)	C12—C7—P1	121.9 (2)
O2—Ca1—N2i	80.48 (6)	C9—C8—C7	119.2 (3)
O2i—Ca1—N2i	90.12 (6)	C9—C8—H8A	120.4
O1—Ca1—N2	80.81 (6)	C7—C8—H8A	120.4
O1i—Ca1—N2	110.51 (6)	C10—C9—C8	121.5 (4)
O2—Ca1—N2	90.12 (6)	C10—C9—H9A	119.2
O2i—Ca1—N2	80.48 (6)	C8—C9—H9A	119.2
N2i—Ca1—N2	165.55 (9)	C9—C10—C11	119.8 (4)
O1—Ca1—P2	97.95 (6)	C9—C10—H10A	120.1
O1i—Ca1—P2	139.82 (5)	C11—C10—H10A	120.1
O2—Ca1—P2	18.93 (4)	C10—C11—C12	119.9 (4)
O2i—Ca1—P2	100.02 (6)	C10—C11—H11A	120.0
N2i—Ca1—P2	61.66 (4)	C12—C11—H11A	120.0
N2—Ca1—P2	108.97 (4)	C11—C12—C7	120.7 (3)
O1—Ca1—P2i	139.82 (5)	C11—C12—H12A	119.6
O1i—Ca1—P2i	97.95 (6)	C7—C12—H12A	119.6
O2—Ca1—P2i	100.02 (6)	N1—C13—N2	129.4 (2)
O2i—Ca1—P2i	18.93 (4)	N1—C13—C14	120.7 (2)
N2i—Ca1—P2i	108.97 (5)	N2—C13—C14	109.96 (18)
N2—Ca1—P2i	61.66 (4)	C19—C14—C15	120.9 (2)
P2—Ca1—P2i	107.00 (3)	C19—C14—C13	106.42 (19)
O1—Ca1—P1	18.51 (4)	C15—C14—C13	132.6 (2)
O1i—Ca1—P1	90.49 (5)	C14—C15—C16	118.0 (2)
O2—Ca1—P1	91.20 (5)	C14—C15—H15A	121.0
O2i—Ca1—P1	141.54 (5)	C16—C15—H15A	121.0
N2i—Ca1—P1	128.23 (4)	C15—C16—C17	120.8 (2)
N2—Ca1—P1	62.42 (4)	C15—C16—H16A	119.6
P2—Ca1—P1	101.274 (17)	C17—C16—H16A	119.6
P2i—Ca1—P1	122.787 (15)	C18—C17—C16	121.1 (2)
O1—Ca1—P1i	90.49 (5)	C18—C17—H17A	119.5
O1i—Ca1—P1i	18.51 (4)	C16—C17—H17A	119.5
O2—Ca1—P1i	141.54 (5)	C19—C18—C17	117.8 (2)
O2i—Ca1—P1i	91.20 (5)	C19—C18—H18A	121.1
N2i—Ca1—P1i	62.42 (4)	C17—C18—H18A	121.1
N2—Ca1—P1i	128.23 (4)	C18—C19—C14	121.4 (2)
P2—Ca1—P1i	122.787 (15)	C18—C19—C20	132.5 (2)
P2i—Ca1—P1i	101.274 (17)	C14—C19—C20	106.04 (19)
P1—Ca1—P1i	103.44 (3)	N3i—C20—N2	129.2 (2)
O1—P1—N1	120.24 (10)	N3i—C20—C19	120.1 (2)
O1—P1—C1	109.60 (13)	N2—C20—C19	110.65 (18)
N1—P1—C1	103.94 (12)	C22—C21—C26	117.6 (3)
O1—P1—C7	110.69 (12)	C22—C21—P2	121.9 (2)
N1—P1—C7	104.01 (11)	C26—C21—P2	120.4 (3)
C1—P1—C7	107.54 (12)	C21—C22—C23	121.3 (4)
N1—P1—Ca1	91.43 (7)	C21—C22—H22A	119.3
C1—P1—Ca1	123.78 (9)	C23—C22—H22A	119.3
C7—P1—Ca1	120.67 (9)	C24—C23—C22	120.9 (5)
O2—P2—N3	119.32 (10)	C24—C23—H23A	119.5
O2—P2—C27	112.18 (13)	C22—C23—H23A	119.5
N3—P2—C27	105.94 (13)	C23—C24—C25	119.8 (4)
O2—P2—C21	108.99 (13)	C23—C24—H24A	120.1
N3—P2—C21	104.66 (12)	C25—C24—H24A	120.1
C27—P2—C21	104.56 (12)	C24—C25—C26	120.5 (4)
N3—P2—Ca1	91.97 (7)	C24—C25—H25A	119.7
C27—P2—Ca1	114.13 (9)	C26—C25—H25A	119.7
C21—P2—Ca1	131.54 (10)	C21—C26—C25	119.7 (4)
P1—O1—Ca1	132.60 (10)	C21—C26—H26A	120.1
P2—O2—Ca1	131.50 (10)	C25—C26—H26A	120.1
C13—N1—P1	128.67 (17)	C32—C27—C28	117.7 (3)
C20—N2—C13	106.88 (18)	C32—C27—P2	124.0 (3)
C20—N2—Ca1	125.26 (14)	C28—C27—P2	118.3 (2)
C13—N2—Ca1	124.95 (14)	C27—C28—C29	120.3 (4)
C20i—N3—P2	127.09 (18)	C27—C28—H28A	119.9
C2—C1—C6	119.0 (3)	C29—C28—H28A	119.9
C2—C1—P1	122.6 (2)	C30—C29—C28	120.3 (4)
C6—C1—P1	118.4 (3)	C30—C29—H29A	119.9
C1—C2—C3	119.6 (4)	C28—C29—H29A	119.9
C1—C2—H2B	120.2	C29—C30—C31	120.1 (4)
C3—C2—H2B	120.2	C29—C30—H30A	120.0
C4—C3—C2	121.7 (5)	C31—C30—H30A	120.0
C4—C3—H3B	119.1	C30—C31—C32	120.7 (4)
C2—C3—H3B	119.1	C30—C31—H31A	119.7
C3—C4—C5	119.8 (4)	C32—C31—H31A	119.7
C3—C4—H4A	120.1	C31—C32—C27	121.0 (4)
C5—C4—H4A	120.1	C31—C32—H32A	119.5
C4—C5—C6	120.9 (5)	C27—C32—H32A	119.5

Symmetry codes: (i) −x, y, −z+1/2.