Bis{6,6′-dimeth­oxy-2,2′-[ethane-1,2-diyl­bis(imino­methyl­ene)]diphenolato(1.5−)-κ4O,N,N′,O′}praeseodymium(III)

Xia, H.-T.; Liu, Y.-F.; Yang, S.-P.; Wang, D.-Q.

doi:10.1107/S1600536809001500

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page m200

doi:10.1107/S1600536809001500

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Bis{6,6′-dimethoxy-2,2′-[ethane-1,2-diylbis(iminomethylene)]diphenolato(1.5−)-κ⁴O,N,N′,O′}praeseodymium(III)

Hai-Tao Xia,^a ^* Yu-Fen Liu,^a Shu-Ping Yang ^a and Da-Qi Wang ^b

^aSchool of Chemical Engineering, Huaihai Institute of Technology, Lianyungang 222005, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: xht161006@hhit.edu.cn

(Received 14 November 2008; accepted 12 January 2009; online 17 January 2009)

The title compound, [Pr(C₁₈H_22.5N₂O₄)₂], is isotypic with its Er and Tb analogues. All interatomic distances, angles and the hydrogen bond geometry are very similar for the three structures..

Related literature

For related structures, see: Liu et al. (2007 ); Xia et al. (2006 ). For isotypic structures, see: Xia et al. (2009a ,b ).

Experimental

Crystal data

[Pr(C₁₈H_22.5N₂O₄)₂]
M_r = 802.67
Orthorhombic, I b a 2
a = 21.977 (3) Å
b = 11.1616 (12) Å
c = 14.1699 (18) Å
V = 3475.8 (7) Å³
Z = 4
Mo Kα radiation
μ = 1.46 mm⁻¹
T = 298 (2) K
0.22 × 0.13 × 0.08 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.740, T_max = 0.892
8635 measured reflections
2878 independent reflections
2230 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.070
S = 1.07
2878 reflections
222 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.69 e Å⁻³
Δρ_min = −0.37 e Å⁻³
Absolute structure: Flack (1983 ), 1271 Friedel pairs
Flack parameter: 0.00 (3)

Table 1
Selected bond lengths (Å)

Pr1—O3	2.200 (4)
Pr1—O3ⁱ	2.200 (4)
Pr1—O1ⁱ	2.204 (4)
Pr1—O1	2.204 (4)
Pr1—N1ⁱ	2.619 (4)
Pr1—N1	2.619 (4)
Pr1—N2ⁱ	2.623 (5)
Pr1—N2	2.623 (5)
Symmetry code: (i) -x+1, -y+1, z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3C⋯O4	0.85	2.12	2.653 (5)	121
N1—H1⋯O4ⁱ	0.91	2.34	3.229 (6)	167
N2—H2⋯O2ⁱ	0.91	2.59	3.464 (6)	162
Symmetry code: (i) -x+1, -y+1, z.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809001500/at2681sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809001500/at2681Isup2.hkl

checkCIF report

Comment top

Diamine derivatives are potentially multidentate ligands. we have recently reported the crystal structure (C₁₈H₂₄O₂N₄) (II) (Xia et al., 2006) which is the ligand of the title compound and two complexes [Ce(C₁₈H₂₂N₂O₄)₂] (III) (Liu et al., 2007), [Er(C₁₈H_22.5N₂O₄)₂] (IV) (Xia et al., 2009). We report here the crystal structure of new rare earth complex , (I).

In the title complex (I), the coordination environment of the Pr atom and coordination modes of (I) ligands to Pr^III ion is in agreement with the complexes reported above (Fig. 1). The average bond lengths of between the Praeseodymium center oxygen atoms are 2.202 (4)Å and nitrogen atom are 2.621 (5) Å, longer than the 2.199 (4)Å and shorter than the 2.624 (4)Å of complexes (III), respectively, shorter than the 2.203 (6)Å and longter than the 2.612 (8)Å of complexes (IV), respectively. The dihedral angles between phenyl ring (C4—C9 ring) and antother phenyl ring are 42.03 (16)°(C12—C17 ring), 47.60 (15)°(C4A—C9A ring) and 15.08 (24)°(C12A—C17A ring) [symmetry codes: (A) 1 - x, 1 - y, z].

In (I), the Pr atom is eight-coordinated by four O atoms and four N atoms from two 6,6'-dimethoxy-2,2'-(ethane-1,2-diyldiiminodimethylene)diphenol. The molecules are connected by van der Waals forces, resulting in a three-dimensional network.

Related literature top

For related structures, see: Liu et al. (2007); Xia et al. (2006). For isotypic structures, see: Xia et al. (2009a,b).

Experimental top

A solution of 6,6'-dimethoxy-2,2'-(ethane-1,2-diyldiiminodimethylene) diphenol (0.328 g, 2 mmol) in ethanol (20 ml), and then a solution of Pr(NO₃)₃.6H₂O (0.435 g, 1 mmol) in ethanol (10 ml) was added. The reaction mixture was stirred for 3 h in the air and then filtered. X-ray quality crystals of (I) were obtained by evaporation of an ethanol solution.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are at the 30% probability level. For clarity, H atoms have been omitted. [Symmetry codes: (A) 1 - x, 1 - y, z].

Bis{6,6'-dimethoxy-2,2'-[ethane-1,2-diylbis(iminomethylene)]diphenolato(1.5-)- κ⁴O,N,N',O'}praeseodymium(III) top

Crystal data top

[Pr(C₁₈H_22.5N₂O₄)₂]	F(000) = 1648
M_r = 802.67	D_x = 1.534 Mg m⁻³
Orthorhombic, Iba2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: I 2 -2c	Cell parameters from 4426 reflections
a = 21.977 (3) Å	θ = 2.9–28.2°
b = 11.1616 (12) Å	µ = 1.46 mm⁻¹
c = 14.1699 (18) Å	T = 298 K
V = 3475.8 (7) Å³	Block, brown
Z = 4	0.22 × 0.13 × 0.08 mm

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	2878 independent reflections
Radiation source: fine-focus sealed tube	2230 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −26→24
T_min = 0.740, T_max = 0.892	k = −10→13
8635 measured reflections	l = −15→16

Refinement top

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)] = 0.028	H-atom parameters constrained
wR(F²) = 0.070	w = 1/[σ²(F_o²) + (0.0246P)² + 7.4954P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
2878 reflections	Δρ_max = 0.69 e Å⁻³
222 parameters	Δρ_min = −0.37 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1271 Freidel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (3)

Crystal data top

[Pr(C₁₈H_22.5N₂O₄)₂]	V = 3475.8 (7) Å³
M_r = 802.67	Z = 4
Orthorhombic, Iba2	Mo Kα radiation
a = 21.977 (3) Å	µ = 1.46 mm⁻¹
b = 11.1616 (12) Å	T = 298 K
c = 14.1699 (18) Å	0.22 × 0.13 × 0.08 mm

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	2878 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2230 reflections with I > 2σ(I)
T_min = 0.740, T_max = 0.892	R_int = 0.030
8635 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	H-atom parameters constrained
wR(F²) = 0.070	Δρ_max = 0.69 e Å⁻³
S = 1.07	Δρ_min = −0.37 e Å⁻³
2878 reflections	Absolute structure: Flack (1983), 1271 Freidel pairs
222 parameters	Absolute structure parameter: 0.00 (3)
1 restraint

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	Occ. (<1)
Pr1	0.5000	0.5000	0.34632 (9)	0.03225 (10)
N1	0.6052 (2)	0.5730 (5)	0.4112 (4)	0.0494 (13)
H1	0.6334	0.5339	0.3757	0.059*
N2	0.5336 (2)	0.7094 (4)	0.2803 (3)	0.0446 (12)
H2	0.5154	0.7641	0.3186	0.054*
O1	0.53496 (16)	0.3653 (4)	0.4463 (3)	0.0437 (9)
O2	0.5617 (2)	0.1320 (4)	0.4296 (4)	0.0719 (14)
O3	0.43210 (16)	0.5583 (3)	0.2419 (3)	0.0395 (8)
H3C	0.4017	0.5132	0.2524	0.059*	0.50
O4	0.31350 (17)	0.5867 (4)	0.2690 (3)	0.0547 (11)
C1	0.6158 (3)	0.7002 (7)	0.3927 (7)	0.063 (2)
H1A	0.6583	0.7191	0.4037	0.075*
H1B	0.5914	0.7481	0.4354	0.075*
C2	0.5994 (3)	0.7299 (6)	0.2921 (6)	0.061 (2)
H2A	0.6091	0.8129	0.2785	0.074*
H2B	0.6221	0.6794	0.2490	0.074*
C3	0.6177 (3)	0.5354 (7)	0.5091 (5)	0.062 (2)
H3A	0.5823	0.5513	0.5482	0.074*
H3B	0.6516	0.5809	0.5342	0.074*
C4	0.6322 (3)	0.4054 (7)	0.5115 (4)	0.0574 (19)
C5	0.5892 (3)	0.3256 (7)	0.4762 (5)	0.048 (2)
C6	0.6047 (3)	0.2033 (7)	0.4686 (5)	0.0616 (19)
C7	0.6621 (3)	0.1636 (9)	0.5003 (6)	0.071 (3)
H7	0.6725	0.0830	0.4968	0.085*
C8	0.7014 (4)	0.2440 (10)	0.5356 (6)	0.082 (3)
H8	0.7394	0.2174	0.5554	0.098*
C9	0.6885 (3)	0.3609 (9)	0.5435 (5)	0.073 (2)
H9	0.7168	0.4128	0.5701	0.088*
C10	0.5795 (4)	0.0130 (7)	0.4047 (8)	0.105 (3)
H10A	0.6162	0.0159	0.3680	0.157*
H10B	0.5478	−0.0239	0.3682	0.157*
H10C	0.5864	−0.0328	0.4610	0.157*
C11	0.5117 (3)	0.7376 (6)	0.1847 (5)	0.0556 (17)
H11A	0.5213	0.6721	0.1422	0.067*
H11B	0.5316	0.8093	0.1616	0.067*
C12	0.4433 (3)	0.7570 (6)	0.1875 (4)	0.0491 (15)
C13	0.4073 (3)	0.6640 (6)	0.2217 (5)	0.0414 (17)
C14	0.3448 (3)	0.6836 (6)	0.2338 (4)	0.0456 (14)
C15	0.3194 (3)	0.7933 (7)	0.2106 (5)	0.0562 (18)
H15	0.2779	0.8067	0.2183	0.067*
C16	0.3569 (4)	0.8827 (7)	0.1757 (6)	0.068 (2)
H16	0.3399	0.9564	0.1600	0.082*
C17	0.4164 (4)	0.8664 (6)	0.1639 (5)	0.066 (2)
H17	0.4403	0.9281	0.1399	0.079*
C18	0.2529 (3)	0.6065 (8)	0.2982 (6)	0.079 (2)
H18A	0.2509	0.6785	0.3351	0.119*
H18B	0.2393	0.5400	0.3356	0.119*
H18C	0.2272	0.6145	0.2438	0.119*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pr1	0.02417 (14)	0.03686 (17)	0.03572 (16)	−0.00020 (19)	0.000	0.000
N1	0.030 (2)	0.060 (3)	0.058 (3)	0.001 (2)	−0.002 (2)	−0.025 (3)
N2	0.036 (3)	0.043 (3)	0.055 (3)	−0.009 (2)	0.014 (2)	−0.004 (2)
O1	0.031 (2)	0.059 (3)	0.040 (2)	0.0115 (19)	−0.0036 (17)	0.005 (2)
O2	0.067 (3)	0.057 (3)	0.092 (4)	0.020 (3)	0.017 (3)	0.023 (3)
O3	0.041 (2)	0.037 (2)	0.041 (2)	0.0023 (19)	−0.0060 (19)	0.0011 (18)
O4	0.035 (2)	0.065 (3)	0.064 (3)	0.005 (2)	−0.0034 (19)	0.002 (2)
C1	0.033 (4)	0.068 (5)	0.088 (5)	−0.013 (3)	0.006 (4)	−0.031 (4)
C2	0.045 (4)	0.050 (4)	0.090 (6)	−0.016 (3)	0.020 (4)	−0.011 (4)
C3	0.044 (4)	0.090 (6)	0.052 (4)	0.001 (3)	−0.008 (3)	−0.025 (4)
C4	0.043 (3)	0.090 (6)	0.040 (4)	0.020 (4)	−0.003 (3)	−0.009 (4)
C5	0.042 (4)	0.069 (6)	0.031 (4)	0.017 (4)	0.006 (3)	0.010 (4)
C6	0.054 (4)	0.082 (5)	0.049 (4)	0.023 (4)	0.008 (3)	0.018 (4)
C7	0.054 (5)	0.091 (7)	0.067 (6)	0.030 (5)	0.013 (4)	0.025 (5)
C8	0.062 (5)	0.116 (8)	0.067 (5)	0.032 (5)	−0.008 (4)	0.013 (5)
C9	0.051 (4)	0.116 (7)	0.054 (4)	0.016 (5)	−0.011 (3)	−0.008 (5)
C10	0.100 (6)	0.066 (5)	0.149 (8)	0.021 (5)	0.023 (6)	0.020 (6)
C11	0.064 (5)	0.044 (3)	0.058 (4)	−0.006 (3)	0.022 (3)	0.002 (3)
C12	0.059 (4)	0.043 (4)	0.045 (3)	0.010 (3)	0.006 (3)	0.004 (3)
C13	0.045 (4)	0.046 (4)	0.033 (4)	0.006 (4)	−0.004 (3)	−0.004 (3)
C14	0.051 (3)	0.049 (4)	0.037 (3)	0.009 (3)	−0.005 (3)	−0.003 (3)
C15	0.053 (4)	0.057 (4)	0.058 (5)	0.016 (4)	−0.008 (3)	−0.007 (3)
C16	0.078 (6)	0.051 (5)	0.074 (5)	0.019 (4)	−0.001 (4)	0.010 (4)
C17	0.079 (5)	0.049 (4)	0.071 (5)	0.005 (4)	0.012 (4)	0.012 (4)
C18	0.044 (4)	0.099 (6)	0.095 (5)	−0.001 (4)	0.001 (4)	0.008 (5)

Geometric parameters (Å, º) top

Pr1—O3	2.200 (4)	C3—H3B	0.9700
Pr1—O3ⁱ	2.200 (4)	C4—C5	1.392 (10)
Pr1—O1ⁱ	2.204 (4)	C4—C9	1.409 (9)
Pr1—O1	2.204 (4)	C5—C6	1.411 (10)
Pr1—N1ⁱ	2.619 (4)	C6—C7	1.411 (9)
Pr1—N1	2.619 (4)	C7—C8	1.344 (12)
Pr1—N2ⁱ	2.623 (5)	C7—H7	0.9300
Pr1—N2	2.623 (5)	C8—C9	1.340 (12)
Pr1—H3C	2.5421	C8—H8	0.9300
N1—C1	1.462 (9)	C9—H9	0.9300
N1—C3	1.475 (8)	C10—H10A	0.9600
N1—H1	0.9100	C10—H10B	0.9600
N2—C11	1.471 (8)	C10—H10C	0.9600
N2—C2	1.472 (8)	C11—C12	1.519 (9)
N2—H2	0.9100	C11—H11A	0.9700
O1—C5	1.340 (7)	C11—H11B	0.9700
O2—C6	1.353 (8)	C12—C13	1.392 (9)
O2—C10	1.428 (9)	C12—C17	1.397 (9)
O3—C13	1.330 (7)	C13—C14	1.402 (8)
O3—H3C	0.8500	C14—C15	1.386 (9)
O4—C14	1.375 (7)	C15—C16	1.386 (11)
O4—C18	1.413 (8)	C15—H15	0.9300
C1—C2	1.508 (9)	C16—C17	1.332 (10)
C1—H1A	0.9700	C16—H16	0.9300
C1—H1B	0.9700	C17—H17	0.9300
C2—H2A	0.9700	C18—H18A	0.9600
C2—H2B	0.9700	C18—H18B	0.9600
C3—C4	1.486 (11)	C18—H18C	0.9600
C3—H3A	0.9700

O3—Pr1—O3ⁱ	95.47 (19)	N2—C2—H2B	110.1
O3—Pr1—O1ⁱ	89.65 (13)	C1—C2—H2B	110.1
O3ⁱ—Pr1—O1ⁱ	150.52 (13)	H2A—C2—H2B	108.4
O3—Pr1—O1	150.52 (13)	N1—C3—C4	109.8 (5)
O3ⁱ—Pr1—O1	89.65 (13)	N1—C3—H3A	109.7
O1ⁱ—Pr1—O1	100.0 (2)	C4—C3—H3A	109.7
O3—Pr1—N1ⁱ	74.28 (15)	N1—C3—H3B	109.7
O3ⁱ—Pr1—N1ⁱ	137.99 (15)	C4—C3—H3B	109.7
O1ⁱ—Pr1—N1ⁱ	71.27 (16)	H3A—C3—H3B	108.2
O1—Pr1—N1ⁱ	82.53 (15)	C5—C4—C9	119.1 (7)
O3—Pr1—N1	137.99 (15)	C5—C4—C3	118.1 (5)
O3ⁱ—Pr1—N1	74.28 (15)	C9—C4—C3	122.7 (7)
O1ⁱ—Pr1—N1	82.53 (15)	O1—C5—C4	120.4 (6)
O1—Pr1—N1	71.27 (16)	O1—C5—C6	120.6 (7)
N1ⁱ—Pr1—N1	138.9 (2)	C4—C5—C6	118.9 (6)
O3—Pr1—N2ⁱ	80.36 (14)	O2—C6—C7	124.7 (7)
O3ⁱ—Pr1—N2ⁱ	71.79 (14)	O2—C6—C5	115.6 (6)
O1ⁱ—Pr1—N2ⁱ	137.63 (14)	C7—C6—C5	119.6 (8)
O1—Pr1—N2ⁱ	73.73 (16)	C8—C7—C6	119.0 (9)
N1ⁱ—Pr1—N2ⁱ	66.38 (16)	C8—C7—H7	120.5
N1—Pr1—N2ⁱ	130.63 (15)	C6—C7—H7	120.5
O3—Pr1—N2	71.79 (14)	C9—C8—C7	123.0 (8)
O3ⁱ—Pr1—N2	80.36 (14)	C9—C8—H8	118.5
O1ⁱ—Pr1—N2	73.73 (16)	C7—C8—H8	118.5
O1—Pr1—N2	137.63 (14)	C8—C9—C4	120.2 (8)
N1ⁱ—Pr1—N2	130.63 (15)	C8—C9—H9	119.9
N1—Pr1—N2	66.38 (16)	C4—C9—H9	119.9
N2ⁱ—Pr1—N2	138.2 (2)	O2—C10—H10A	109.5
O3—Pr1—H3C	18.9	O2—C10—H10B	109.5
O3ⁱ—Pr1—H3C	104.0	H10A—C10—H10B	109.5
O1ⁱ—Pr1—H3C	90.0	O2—C10—H10C	109.5
O1—Pr1—H3C	132.2	H10A—C10—H10C	109.5
N1ⁱ—Pr1—H3C	56.7	H10B—C10—H10C	109.5
N1—Pr1—H3C	156.4	N2—C11—C12	109.3 (5)
N2ⁱ—Pr1—H3C	68.0	N2—C11—H11A	109.8
N2—Pr1—H3C	90.0	C12—C11—H11A	109.8
C1—N1—C3	114.5 (6)	N2—C11—H11B	109.8
C1—N1—Pr1	112.3 (4)	C12—C11—H11B	109.8
C3—N1—Pr1	113.9 (4)	H11A—C11—H11B	108.3
C1—N1—H1	105.0	C13—C12—C17	119.7 (6)
C3—N1—H1	105.0	C13—C12—C11	117.7 (5)
Pr1—N1—H1	105.0	C17—C12—C11	122.4 (6)
C11—N2—C2	113.1 (5)	O3—C13—C12	120.2 (6)
C11—N2—Pr1	115.2 (4)	O3—C13—C14	120.9 (6)
C2—N2—Pr1	112.0 (4)	C12—C13—C14	118.9 (6)
C11—N2—H2	105.1	O4—C14—C15	125.4 (6)
C2—N2—H2	105.1	O4—C14—C13	114.3 (5)
Pr1—N2—H2	105.1	C15—C14—C13	120.2 (6)
C5—O1—Pr1	137.6 (4)	C16—C15—C14	118.8 (7)
C6—O2—C10	117.1 (6)	C16—C15—H15	120.6
C13—O3—Pr1	133.2 (4)	C14—C15—H15	120.6
C13—O3—H3C	103.9	C17—C16—C15	122.0 (7)
Pr1—O3—H3C	103.9	C17—C16—H16	119.0
C14—O4—C18	117.0 (5)	C15—C16—H16	119.0
N1—C1—C2	110.2 (6)	C16—C17—C12	120.3 (7)
N1—C1—H1A	109.6	C16—C17—H17	119.8
C2—C1—H1A	109.6	C12—C17—H17	119.8
N1—C1—H1B	109.6	O4—C18—H18A	109.5
C2—C1—H1B	109.6	O4—C18—H18B	109.5
H1A—C1—H1B	108.1	H18A—C18—H18B	109.5
N2—C2—C1	108.0 (6)	O4—C18—H18C	109.5
N2—C2—H2A	110.1	H18A—C18—H18C	109.5
C1—C2—H2A	110.1	H18B—C18—H18C	109.5

O3—Pr1—N1—C1	19.9 (5)	N1—C1—C2—N2	63.9 (7)
O3ⁱ—Pr1—N1—C1	100.5 (5)	C1—N1—C3—C4	−155.2 (5)
O1ⁱ—Pr1—N1—C1	−61.2 (4)	Pr1—N1—C3—C4	73.6 (5)
O1—Pr1—N1—C1	−164.4 (5)	N1—C3—C4—C5	−57.9 (8)
N1ⁱ—Pr1—N1—C1	−111.1 (5)	N1—C3—C4—C9	118.9 (6)
N2ⁱ—Pr1—N1—C1	148.5 (4)	Pr1—O1—C5—C4	53.9 (9)
N2—Pr1—N1—C1	14.3 (4)	Pr1—O1—C5—C6	−123.3 (6)
O3—Pr1—N1—C3	152.2 (4)	C9—C4—C5—O1	179.2 (6)
O3ⁱ—Pr1—N1—C3	−127.3 (4)	C3—C4—C5—O1	−3.9 (9)
O1ⁱ—Pr1—N1—C3	71.1 (4)	C9—C4—C5—C6	−3.5 (10)
O1—Pr1—N1—C3	−32.2 (4)	C3—C4—C5—C6	173.4 (6)
N1ⁱ—Pr1—N1—C3	21.1 (4)	C10—O2—C6—C7	−10.9 (10)
N2ⁱ—Pr1—N1—C3	−79.3 (4)	C10—O2—C6—C5	168.7 (7)
N2—Pr1—N1—C3	146.6 (4)	O1—C5—C6—O2	0.3 (9)
O3—Pr1—N2—C11	−26.1 (4)	C4—C5—C6—O2	−177.0 (6)
O3ⁱ—Pr1—N2—C11	72.9 (4)	O1—C5—C6—C7	179.9 (6)
O1ⁱ—Pr1—N2—C11	−121.3 (4)	C4—C5—C6—C7	2.6 (10)
O1—Pr1—N2—C11	151.7 (3)	O2—C6—C7—C8	178.3 (7)
N1ⁱ—Pr1—N2—C11	−75.0 (4)	C5—C6—C7—C8	−1.2 (11)
N1—Pr1—N2—C11	149.9 (4)	C6—C7—C8—C9	0.9 (13)
N2ⁱ—Pr1—N2—C11	24.7 (3)	C7—C8—C9—C4	−1.9 (13)
O3—Pr1—N2—C2	−157.4 (5)	C5—C4—C9—C8	3.2 (11)
O3ⁱ—Pr1—N2—C2	−58.3 (4)	C3—C4—C9—C8	−173.5 (7)
O1ⁱ—Pr1—N2—C2	107.5 (5)	C2—N2—C11—C12	−160.1 (5)
O1—Pr1—N2—C2	20.5 (5)	Pr1—N2—C11—C12	69.3 (5)
N1ⁱ—Pr1—N2—C2	153.8 (4)	N2—C11—C12—C13	−57.6 (7)
N1—Pr1—N2—C2	18.7 (4)	N2—C11—C12—C17	117.5 (7)
N2ⁱ—Pr1—N2—C2	−106.6 (4)	Pr1—O3—C13—C12	64.1 (8)
O3—Pr1—O1—C5	144.6 (6)	Pr1—O3—C13—C14	−116.3 (6)
O3ⁱ—Pr1—O1—C5	44.1 (6)	C17—C12—C13—O3	178.1 (6)
O1ⁱ—Pr1—O1—C5	−107.9 (6)	C11—C12—C13—O3	−6.7 (9)
N1ⁱ—Pr1—O1—C5	−177.3 (6)	C17—C12—C13—C14	−1.5 (10)
N1—Pr1—O1—C5	−29.4 (6)	C11—C12—C13—C14	173.8 (5)
N2ⁱ—Pr1—O1—C5	115.2 (6)	C18—O4—C14—C15	−11.0 (9)
N2—Pr1—O1—C5	−31.1 (7)	C18—O4—C14—C13	169.3 (6)
O3ⁱ—Pr1—O3—C13	−117.1 (6)	O3—C13—C14—O4	1.1 (9)
O1ⁱ—Pr1—O3—C13	33.8 (5)	C12—C13—C14—O4	−179.3 (5)
O1—Pr1—O3—C13	143.9 (5)	O3—C13—C14—C15	−178.6 (6)
N1ⁱ—Pr1—O3—C13	104.4 (6)	C12—C13—C14—C15	0.9 (10)
N1—Pr1—O3—C13	−44.6 (6)	O4—C14—C15—C16	−179.9 (6)
N2ⁱ—Pr1—O3—C13	172.5 (6)	C13—C14—C15—C16	−0.2 (11)
N2—Pr1—O3—C13	−39.1 (5)	C14—C15—C16—C17	0.0 (12)
C3—N1—C1—C2	−177.7 (5)	C15—C16—C17—C12	−0.5 (12)
Pr1—N1—C1—C2	−45.7 (6)	C13—C12—C17—C16	1.2 (11)
C11—N2—C2—C1	178.9 (6)	C11—C12—C17—C16	−173.8 (7)
Pr1—N2—C2—C1	−48.8 (6)

Symmetry code: (i) −x+1, −y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3C···O4	0.85	2.12	2.653 (5)	121
N1—H1···O4ⁱ	0.91	2.34	3.229 (6)	167
N2—H2···O2ⁱ	0.91	2.59	3.464 (6)	162

Symmetry code: (i) −x+1, −y+1, z.

Experimental details

Crystal data
Chemical formula	[Pr(C₁₈H_22.5N₂O₄)₂]
M_r	802.67
Crystal system, space group	Orthorhombic, Iba2
Temperature (K)	298
a, b, c (Å)	21.977 (3), 11.1616 (12), 14.1699 (18)
V (Å³)	3475.8 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.46
Crystal size (mm)	0.22 × 0.13 × 0.08

Data collection
Diffractometer	Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.740, 0.892
No. of measured, independent and observed [I > 2σ(I)] reflections	8635, 2878, 2230
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.070, 1.07
No. of reflections	2878
No. of parameters	222
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.69, −0.37
Absolute structure	Flack (1983), 1271 Freidel pairs
Absolute structure parameter	0.00 (3)

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Pr1—O3	2.200 (4)	Pr1—N1ⁱ	2.619 (4)
Pr1—O3ⁱ	2.200 (4)	Pr1—N1	2.619 (4)
Pr1—O1ⁱ	2.204 (4)	Pr1—N2ⁱ	2.623 (5)
Pr1—O1	2.204 (4)	Pr1—N2	2.623 (5)

Symmetry code: (i) −x+1, −y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3C···O4	0.85	2.12	2.653 (5)	120.7
N1—H1···O4ⁱ	0.91	2.34	3.229 (6)	167.0
N2—H2···O2ⁱ	0.91	2.59	3.464 (6)	162.3

Symmetry code: (i) −x+1, −y+1, z.

Acknowledgements

We acknowledge the financial support of the Huaihai Institute of Technology Science Foundation.

References

Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Liu, Y.-F., Xia, H.-T., Wang, D.-Q. & Yang, S.-P. (2007). Acta Cryst. E63, m484–m486. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens. (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Xia, H.-T., Liu, Y.-F., Yang, S.-P. & Wang, D.-Q. (2006). Acta Cryst. E62, o5864–o5865. Web of Science CSD CrossRef IUCr Journals Google Scholar
Xia, H.-T., Liu, Y.-F., Yang, S.-P. & Wang, D.-Q. (2009a). Acta Cryst. E65, m201. Web of Science CSD CrossRef IUCr Journals Google Scholar
Xia, H.-T., Rong, D.-F., Zhang, Y.-Y., Yang, S.-P. & Wang, D.-Q. (2009b). Acta Cryst. E65, m198–m199. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 65| Part 2| February 2009| Page m200

doi:10.1107/S1600536809001500

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