Bis[1,3-bis­(diphenyl­phosphinoylimino)isoindolinato-κ3O,N,O′]calcium(II)

Li, Z.; Shang, D.; Guo, J.

doi:10.1107/S1600536807065440

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page m160

https://doi.org/10.1107/S1600536807065440

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Bis[1,3-bis(diphenylphosphinoylimino)isoindolinato-κ³O,N,O′]calcium(II)

Zhiying Li,^a Donglin Shang ^b and Jianping Guo ^b ^*

^aDepartment of Chemistry, Xinzhou Teachers' University, Xinzhou 034000, People's Republic of China, and ^bThe Institute of Applied Chemistry, Shanxi University, Taiyuan 030006, People's Republic of China
^*Correspondence e-mail: guojp@sxu.edu.cn

(Received 26 October 2007; accepted 4 December 2007; online 12 December 2007)

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, C 2/c
a = 26.351 (2) Å
b = 12.4790 (11) Å
c = 21.1997 (19) Å
β = 126.1720 (10)°
V = 5627.4 (9) Å³
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[F² > 2σ(F²)] = 0.050
wR(F²) = 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

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) $[-x, y, -z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807065440/ww2103sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807065440/ww2103Isup2.hkl

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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).

Structure description top

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

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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(Sheldrick, 1999).

Figures top

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

Bis[1,3-bis(diphenylphosphinoylimino)isoindolinato-κ³O,N,O']calcium(II) top

Crystal data top

[Ca(C₃₂H₂₄N₃O₂P₂)₂]	F(000) = 2344
M_r = 1129.04	D_x = 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 = 2.4–25.9°
b = 12.4790 (11) Å	µ = 0.28 mm⁻¹
c = 21.1997 (19) Å	T = 293 K
β = 126.172 (1)°	Block, pink
V = 5627.4 (9) Å³	0.20 × 0.15 × 0.10 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	4959 independent reflections
Radiation source: fine-focus sealed tube	4175 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ω scan	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −31→17
T_min = 0.837, T_max = 0.973	k = −14→14
11452 measured reflections	l = −22→25

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.075P)² + 4.1489P] where P = (F_o² + 2F_c²)/3
4959 reflections	(Δ/σ)_max = 0.001
357 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

[Ca(C₃₂H₂₄N₃O₂P₂)₂]	V = 5627.4 (9) Å³
M_r = 1129.04	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 26.351 (2) Å	µ = 0.28 mm⁻¹
b = 12.4790 (11) Å	T = 293 K
c = 21.1997 (19) Å	0.20 × 0.15 × 0.10 mm
β = 126.172 (1)°

Data collection top

Bruker SMART CCD diffractometer	4959 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4175 reflections with I > 2σ(I)
T_min = 0.837, T_max = 0.973	R_int = 0.019
11452 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.04	Δρ_max = 0.40 e Å⁻³
4959 reflections	Δρ_min = −0.25 e Å⁻³
357 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
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 (Å²) top

	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, º) top

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 code: (i) −x, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Ca(C₃₂H₂₄N₃O₂P₂)₂]
M_r	1129.04
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	26.351 (2), 12.4790 (11), 21.1997 (19)
β (°)	126.172 (1)
V (Å³)	5627.4 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.20 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.837, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	11452, 4959, 4175
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.135, 1.04
No. of reflections	4959
No. of parameters	357
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.25

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL/PC (Sheldrick, 1999), SHELXTL/PC(Sheldrick, 1999).

Selected geometric parameters (Å, º) top

Ca1—O1	2.2581 (18)	P1—O1	1.4837 (18)
Ca1—O2	2.2646 (18)	P2—O2	1.4888 (19)
Ca1—N2	2.5513 (18)

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

Symmetry code: (i) −x, y, −z+1/2.

Acknowledgements

This work was carried out under the sponsorship of the Overseas Foundation of Shanxi Province, People's Republic of China.

References

Bruker (2000). SMART (Version 5.0) and SAINT (Version 6.02). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cole, M. L., Deacon, G. B., Forsyth, C. M., Konstas, K. & Junk, P. C. (2006). Dalton Trans. pp. 3360–3367. Web of Science CSD CrossRef Google Scholar
Shang, D.-L. (2007). MSc thesis, Shanxi University, People's Republic of China. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1999). SHELXTL/PC. Version 6.10. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar