metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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catena-Poly[[[(1,10-phenanthroline-κ2N,N′)praseodymium(III)]-di-μ-4-hy­droxy­benzoato-κ4O1:O1′-μ-nitrato-κ3O,O′:O] bis­­(1,10-phenanthroline)]

aCollege of Materials Science and Engineering, China Jiliang University, Hangzhou 310018, People's Republic of China
*Correspondence e-mail: wxqnano@cjlu.edu.cn

(Received 26 April 2012; accepted 30 June 2012; online 4 August 2012)

The title complex, [Pr(C7H5O3)2(NO3)(C12H8N2)]·2C12H8N2, has a polymeric chain structure, with two uncoordinated 1,10-phenanthroline mol­ecules in the lattice. The PrIII centre has a monocapped square-anti­prismatic coordination geometry, comprised of two N atoms from one chelating 1,10-phenanthroline ligand, four carboxyl­ate O atoms from four 4-hy­droxy­benzoate anions and three O atoms from two nitrate anions. The 4-hy­droxy­benzoate and nitrate anions function as μ2-bridging ligands and link the PrIII ions into a one-dimensional chain structure along the c axis. Inter­molecular O—H⋯N hydrogen bonds are observed between the 4-hy­droxy­benzoate anions and the uncoordinated 1,10-phenanthroline mol­ecules.

Related literature

For related structures, see: Zhou et al. (2008[Zhou, Y. X., Shen, X. Q., Zhang, H. Y., Du, C. X., Wu, B. L. & Hou, H. W. (2008). J. Coord. Chem. E61, 3981-3992.]); Zhu et al. (2010[Zhu, Y.-M., Feng, P.-P., Yang, Y.-Y. & Ng, S. W. (2010). Acta Cryst. E66, m54-m55.])

[Scheme 1]

Experimental

Crystal data
  • [Pr(C7H5O3)2(NO3)(C12H8N2)]·2C12H8N2

  • Mr = 1017.75

  • Monoclinic, P 21 /c

  • a = 21.5625 (2) Å

  • b = 23.4621 (2) Å

  • c = 8.6030 (1) Å

  • β = 98.899 (1)°

  • V = 4299.88 (7) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 9.27 mm−1

  • T = 291 K

  • 0.40 × 0.33 × 0.30 mm

Data collection
  • Oxford Diffraction Gemini S Ultra diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis PRO, CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]) Tmin = 0.119, Tmax = 0.167

  • 13264 measured reflections

  • 7308 independent reflections

  • 6794 reflections with I > 2σ(I)

  • Rint = 0.029

Refinement
  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 0.092

  • S = 1.06

  • 7308 reflections

  • 606 parameters

  • H-atom parameters constrained

  • Δρmax = 0.74 e Å−3

  • Δρmin = −1.31 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O6—H6⋯N4i 0.82 2.07 2.851 (4) 158
O3—H3⋯N6ii 0.82 2.04 2.782 (5) 150
Symmetry codes: (i) [x+1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (ii) -x+1, -y+1, -z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis PRO, CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis PRO, CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.

Supporting information


Related literature top

For related structures, see: Zhou et al. (2008); Zhu et al. (2010)

Experimental top

Each reagent was commercially available and of analytical grade. Pr(NO3)3.6H2O (0.217 g, 0.5 mmol), p-Hydroxybenzoic acid (0.069 g 0.5 mmol), 1, 10-phenanthroline (0.090 g, 0.5 mmol) and NaHCO3 (0.042 g, 0.5 mmol) were dissolved in water-ethanol solution (10 ml, 5:5). The solution was refluxed for 4 h, and filtered after cooling to room temperature. White single crystals were obtained from the filtrate after 7 days.

Refinement top

H atoms were positioned geometrically (C—H = 0.93 Å and O—H = 0.82 Å) and refined as riding, with Uiso (H) = 1.2Ueq (C) and Uiso(H) = 1.5Ueq (O).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of title compound. Displacement ellipsoids are drawn at the 30% probablility level and H atoms are omitted for clarity.
[Figure 2] Fig. 2. One-dimensional network structure view along b direction.
catena-Poly[[[(1,10-phenanthroline- κ2N,N')praseodymium(III)]-di-µ-4-hydroxybenzoato- κ4O1:O1'-µ-nitrato-κ3O,O':O] bis(1,10-phenanthroline)] top
Crystal data top
[Pr(C7H5O3)2(NO3)(C12H8N2)]·2C12H8N2F(000) = 2056
Mr = 1017.75Dx = 1.572 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybcCell parameters from 9626 reflections
a = 21.5625 (2) Åθ = 1.9–67.4°
b = 23.4621 (2) ŵ = 9.27 mm1
c = 8.6030 (1) ÅT = 291 K
β = 98.899 (1)°Needle, white
V = 4299.88 (7) Å30.40 × 0.33 × 0.30 mm
Z = 4
Data collection top
Oxford Diffraction Gemini S Ultra
diffractometer
7308 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source6794 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.029
Detector resolution: 15.9149 pixels mm-1θmax = 65.1°, θmin = 2.1°
ω scansh = 2525
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2006)
k = 2716
Tmin = 0.119, Tmax = 0.167l = 910
13264 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.060P)2]
where P = (Fo2 + 2Fc2)/3
7308 reflections(Δ/σ)max = 0.001
606 parametersΔρmax = 0.74 e Å3
0 restraintsΔρmin = 1.31 e Å3
Crystal data top
[Pr(C7H5O3)2(NO3)(C12H8N2)]·2C12H8N2V = 4299.88 (7) Å3
Mr = 1017.75Z = 4
Monoclinic, P21/cCu Kα radiation
a = 21.5625 (2) ŵ = 9.27 mm1
b = 23.4621 (2) ÅT = 291 K
c = 8.6030 (1) Å0.40 × 0.33 × 0.30 mm
β = 98.899 (1)°
Data collection top
Oxford Diffraction Gemini S Ultra
diffractometer
7308 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2006)
6794 reflections with I > 2σ(I)
Tmin = 0.119, Tmax = 0.167Rint = 0.029
13264 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.092H-atom parameters constrained
S = 1.06Δρmax = 0.74 e Å3
7308 reflectionsΔρmin = 1.31 e Å3
606 parameters
Special details top

Experimental. CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
xyzUiso*/Ueq
Pr10.911380 (7)0.703539 (6)0.660845 (17)0.02673 (8)
O10.82724 (10)0.69075 (10)0.8105 (3)0.0402 (5)
O20.82646 (10)0.74065 (11)1.0300 (3)0.0446 (5)
O30.54691 (13)0.65243 (17)0.9284 (4)0.0741 (10)
H30.53070.63760.84570.111*
O40.99741 (10)0.76381 (10)0.6186 (3)0.0388 (5)
O50.98379 (10)0.81352 (10)0.3967 (3)0.0393 (5)
O61.27882 (11)0.83426 (15)0.5929 (3)0.0609 (8)
H61.28910.85010.51590.091*
O70.85863 (12)0.63832 (10)0.4358 (3)0.0473 (6)
O80.91180 (11)0.70593 (8)0.3492 (3)0.0344 (5)
O90.87386 (16)0.63694 (11)0.1925 (3)0.0620 (8)
N10.91051 (12)0.58977 (11)0.7443 (3)0.0372 (6)
N20.99832 (12)0.63129 (11)0.5726 (3)0.0360 (6)
N30.29434 (16)0.53994 (16)0.9226 (4)0.0588 (8)
N40.32464 (19)0.64182 (15)0.8063 (4)0.0628 (9)
N50.50294 (18)0.33752 (18)0.4667 (5)0.0684 (10)
N60.52702 (16)0.42317 (16)0.2691 (4)0.0608 (9)
N70.88073 (13)0.65978 (11)0.3208 (3)0.0382 (6)
C10.86749 (17)0.56790 (15)0.8203 (4)0.0452 (8)
H10.83330.59050.83390.054*
C20.8705 (2)0.51245 (17)0.8815 (5)0.0570 (10)
H20.83850.49870.93240.068*
C30.9202 (2)0.47938 (16)0.8658 (4)0.0560 (10)
H3A0.92300.44260.90640.067*
C40.96762 (18)0.50076 (15)0.7881 (4)0.0455 (8)
C51.0222 (2)0.46801 (16)0.7694 (4)0.0542 (9)
H51.02710.43160.81250.065*
C61.06627 (19)0.48895 (16)0.6909 (5)0.0532 (9)
H6A1.10140.46700.68100.064*
C71.05998 (16)0.54452 (15)0.6224 (4)0.0450 (8)
C81.10422 (18)0.56691 (18)0.5375 (5)0.0554 (10)
H81.14010.54610.52690.066*
C91.09484 (17)0.61956 (18)0.4694 (5)0.0541 (9)
H91.12400.63490.41190.065*
C101.04075 (16)0.64978 (15)0.4880 (4)0.0440 (8)
H101.03400.68490.43820.053*
C111.00721 (15)0.57883 (13)0.6386 (4)0.0360 (7)
C120.96066 (15)0.55657 (13)0.7261 (4)0.0368 (7)
C130.80099 (15)0.70958 (12)0.9199 (4)0.0322 (7)
C140.73337 (15)0.69387 (13)0.9191 (4)0.0334 (6)
C150.69901 (15)0.66640 (15)0.7909 (4)0.0393 (7)
H150.71820.65730.70440.047*
C160.63630 (16)0.65238 (16)0.7902 (4)0.0470 (8)
H160.61350.63470.70280.056*
C170.60788 (16)0.66489 (18)0.9204 (5)0.0517 (9)
C180.64241 (19)0.6915 (2)1.0494 (5)0.0602 (11)
H180.62390.69941.13770.072*
C190.70412 (18)0.70630 (15)1.0472 (5)0.0475 (9)
H190.72650.72501.13350.057*
C201.01715 (15)0.79388 (12)0.5157 (4)0.0317 (7)
C211.08667 (14)0.80619 (13)0.5374 (4)0.0312 (6)
C221.12756 (16)0.77961 (17)0.6560 (4)0.0457 (8)
H221.11190.75510.72550.055*
C231.19154 (18)0.78935 (18)0.6716 (5)0.0543 (10)
H231.21850.77130.75130.065*
C241.21567 (15)0.82586 (16)0.5690 (4)0.0432 (8)
C251.17529 (15)0.85264 (15)0.4508 (4)0.0409 (7)
H251.19080.87760.38220.049*
C261.11146 (15)0.84181 (14)0.4357 (4)0.0371 (7)
H261.08460.85910.35450.045*
C270.2817 (2)0.4893 (2)0.9770 (7)0.0762 (14)
H270.28780.48381.08530.091*
C280.2599 (3)0.4442 (3)0.8801 (10)0.097 (2)
H280.25210.40920.92370.116*
C290.2501 (2)0.4509 (3)0.7224 (9)0.0909 (18)
H290.23430.42090.65730.109*
C300.26354 (17)0.5030 (2)0.6578 (6)0.0656 (12)
C310.2559 (2)0.5159 (3)0.4895 (6)0.0795 (17)
H310.23960.48800.41780.095*
C320.2714 (2)0.5660 (3)0.4363 (6)0.0729 (14)
H320.26570.57240.32830.087*
C330.29633 (18)0.6099 (2)0.5385 (5)0.0578 (11)
C340.3163 (2)0.6624 (2)0.4868 (6)0.0741 (14)
H340.31260.67000.37960.089*
C350.3411 (4)0.7024 (2)0.5929 (8)0.093 (2)
H350.35640.73680.56040.112*
C360.3430 (3)0.6902 (2)0.7513 (7)0.0863 (17)
H360.35830.71820.82370.104*
C370.30263 (17)0.60086 (18)0.7031 (4)0.0505 (9)
C380.28600 (16)0.54654 (18)0.7640 (5)0.0508 (9)
C390.4948 (3)0.2955 (2)0.5625 (8)0.0887 (18)
H390.47290.26350.52040.106*
C400.5173 (4)0.2960 (3)0.7245 (9)0.108 (3)
H400.51150.26480.78730.130*
C410.5475 (3)0.3430 (4)0.7867 (7)0.103 (2)
H410.56210.34460.89420.124*
C420.5571 (2)0.3895 (3)0.6909 (6)0.0754 (15)
C430.5878 (2)0.4410 (4)0.7490 (7)0.095 (2)
H430.60260.44430.85600.113*
C440.5958 (2)0.4845 (3)0.6533 (8)0.092 (2)
H440.61460.51790.69550.110*
C450.57586 (18)0.4804 (2)0.4878 (7)0.0728 (14)
C460.5861 (2)0.5236 (2)0.3827 (9)0.0855 (17)
H460.60470.55770.42030.103*
C470.5686 (2)0.5157 (3)0.2249 (10)0.0897 (18)
H470.57630.54340.15290.108*
C480.5387 (2)0.4646 (2)0.1750 (7)0.0743 (13)
H480.52620.45950.06760.089*
C490.54567 (17)0.42982 (19)0.4263 (5)0.0579 (10)
C500.53442 (17)0.3839 (2)0.5292 (5)0.0589 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pr10.02430 (11)0.03072 (12)0.02603 (11)0.00020 (5)0.00666 (7)0.00008 (5)
O10.0344 (11)0.0491 (12)0.0408 (13)0.0055 (10)0.0173 (10)0.0017 (10)
O20.0381 (12)0.0556 (14)0.0408 (13)0.0136 (11)0.0080 (10)0.0071 (11)
O30.0370 (14)0.111 (3)0.078 (2)0.0256 (15)0.0191 (14)0.0280 (19)
O40.0333 (10)0.0483 (13)0.0367 (12)0.0096 (9)0.0113 (9)0.0016 (10)
O50.0331 (11)0.0512 (13)0.0323 (11)0.0029 (10)0.0008 (9)0.0005 (10)
O60.0308 (12)0.102 (2)0.0493 (15)0.0079 (13)0.0055 (11)0.0225 (15)
O70.0578 (14)0.0437 (13)0.0404 (13)0.0166 (11)0.0074 (11)0.0008 (10)
O80.0381 (12)0.0333 (12)0.0330 (12)0.0010 (8)0.0090 (10)0.0008 (8)
O90.100 (2)0.0472 (14)0.0361 (13)0.0003 (15)0.0019 (14)0.0124 (11)
N10.0403 (14)0.0380 (14)0.0334 (13)0.0007 (11)0.0057 (11)0.0008 (11)
N20.0361 (13)0.0383 (14)0.0349 (13)0.0030 (11)0.0101 (11)0.0013 (11)
N30.0498 (18)0.071 (2)0.057 (2)0.0027 (16)0.0108 (15)0.0065 (17)
N40.085 (3)0.055 (2)0.0530 (19)0.0041 (18)0.0268 (19)0.0061 (16)
N50.059 (2)0.086 (3)0.060 (2)0.004 (2)0.0087 (18)0.003 (2)
N60.0463 (17)0.068 (2)0.066 (2)0.0057 (16)0.0029 (16)0.0012 (18)
N70.0494 (15)0.0292 (13)0.0352 (15)0.0003 (12)0.0043 (12)0.0014 (11)
C10.0495 (19)0.0416 (18)0.0469 (19)0.0023 (15)0.0156 (16)0.0044 (15)
C20.071 (3)0.052 (2)0.052 (2)0.0089 (19)0.023 (2)0.0068 (17)
C30.083 (3)0.0395 (18)0.046 (2)0.0005 (19)0.012 (2)0.0078 (16)
C40.062 (2)0.0403 (17)0.0318 (16)0.0057 (16)0.0014 (15)0.0013 (14)
C50.077 (3)0.0399 (18)0.0433 (19)0.0168 (19)0.0006 (19)0.0007 (15)
C60.059 (2)0.047 (2)0.051 (2)0.0202 (17)0.0000 (18)0.0073 (17)
C70.0457 (18)0.0481 (19)0.0394 (17)0.0121 (15)0.0011 (15)0.0086 (15)
C80.0423 (18)0.063 (2)0.061 (2)0.0181 (17)0.0112 (17)0.0090 (19)
C90.0437 (19)0.062 (2)0.062 (2)0.0063 (17)0.0236 (18)0.0072 (19)
C100.0434 (18)0.0438 (18)0.0481 (19)0.0003 (14)0.0171 (15)0.0040 (15)
C110.0368 (15)0.0385 (17)0.0315 (15)0.0068 (13)0.0013 (12)0.0072 (13)
C120.0434 (16)0.0364 (16)0.0294 (15)0.0030 (13)0.0026 (13)0.0046 (12)
C130.0292 (15)0.0345 (15)0.0343 (17)0.0015 (11)0.0088 (13)0.0078 (12)
C140.0297 (15)0.0376 (15)0.0339 (16)0.0031 (12)0.0080 (13)0.0012 (12)
C150.0346 (15)0.0486 (18)0.0353 (16)0.0042 (14)0.0071 (13)0.0068 (14)
C160.0372 (17)0.057 (2)0.0459 (19)0.0091 (15)0.0035 (15)0.0128 (16)
C170.0328 (16)0.066 (2)0.057 (2)0.0124 (16)0.0119 (16)0.0113 (18)
C180.043 (2)0.087 (3)0.056 (2)0.013 (2)0.0251 (19)0.024 (2)
C190.0377 (19)0.065 (2)0.041 (2)0.0108 (15)0.0098 (16)0.0185 (15)
C200.0310 (16)0.0336 (16)0.0319 (16)0.0030 (11)0.0090 (13)0.0083 (12)
C210.0299 (15)0.0368 (15)0.0277 (15)0.0026 (12)0.0064 (12)0.0029 (12)
C220.0383 (17)0.058 (2)0.0409 (18)0.0041 (16)0.0072 (15)0.0152 (17)
C230.0362 (19)0.079 (3)0.047 (2)0.0011 (17)0.0010 (16)0.0241 (18)
C240.0317 (15)0.059 (2)0.0392 (17)0.0079 (15)0.0059 (13)0.0031 (15)
C250.0370 (16)0.0492 (19)0.0370 (17)0.0066 (14)0.0071 (14)0.0091 (14)
C260.0331 (15)0.0425 (17)0.0355 (16)0.0029 (13)0.0047 (13)0.0047 (13)
C270.061 (3)0.077 (3)0.092 (4)0.006 (2)0.016 (3)0.024 (3)
C280.065 (3)0.074 (4)0.154 (6)0.010 (3)0.026 (4)0.021 (4)
C290.055 (3)0.084 (4)0.134 (5)0.019 (3)0.014 (3)0.034 (4)
C300.0308 (17)0.077 (3)0.089 (3)0.0004 (19)0.0083 (19)0.024 (2)
C310.040 (2)0.117 (5)0.078 (3)0.006 (2)0.002 (2)0.049 (3)
C320.045 (2)0.118 (4)0.055 (3)0.015 (3)0.0059 (19)0.018 (3)
C330.0412 (19)0.088 (3)0.046 (2)0.021 (2)0.0110 (16)0.002 (2)
C340.072 (3)0.099 (4)0.056 (3)0.028 (3)0.026 (2)0.023 (3)
C350.133 (6)0.070 (4)0.086 (4)0.017 (3)0.047 (4)0.018 (3)
C360.130 (5)0.056 (3)0.082 (4)0.001 (3)0.047 (4)0.002 (3)
C370.0444 (18)0.067 (2)0.0424 (19)0.0175 (17)0.0140 (15)0.0004 (17)
C380.0319 (16)0.066 (2)0.056 (2)0.0061 (16)0.0088 (15)0.0082 (18)
C390.088 (4)0.094 (4)0.089 (4)0.003 (3)0.029 (4)0.014 (3)
C400.112 (6)0.137 (7)0.083 (5)0.021 (4)0.039 (4)0.035 (4)
C410.084 (4)0.169 (7)0.060 (3)0.034 (4)0.019 (3)0.001 (4)
C420.047 (2)0.124 (5)0.056 (3)0.020 (3)0.011 (2)0.017 (3)
C430.053 (3)0.157 (6)0.073 (4)0.010 (3)0.006 (2)0.056 (4)
C440.050 (3)0.122 (5)0.105 (4)0.000 (3)0.011 (3)0.061 (4)
C450.0330 (19)0.081 (3)0.103 (4)0.012 (2)0.008 (2)0.037 (3)
C460.048 (3)0.061 (3)0.150 (6)0.005 (2)0.024 (3)0.013 (4)
C470.050 (3)0.082 (4)0.140 (6)0.013 (2)0.023 (3)0.022 (4)
C480.054 (2)0.077 (3)0.092 (4)0.007 (2)0.009 (2)0.015 (3)
C490.0313 (16)0.071 (3)0.070 (3)0.0110 (17)0.0049 (17)0.016 (2)
C500.0372 (18)0.087 (3)0.053 (2)0.0113 (19)0.0060 (16)0.011 (2)
Geometric parameters (Å, º) top
Pr1—O2i2.387 (2)C15—H150.9300
Pr1—O5ii2.395 (2)C16—C171.389 (5)
Pr1—O12.400 (2)C16—H160.9300
Pr1—O42.404 (2)C17—C181.385 (6)
Pr1—O72.589 (2)C18—C191.378 (5)
Pr1—O8ii2.671 (2)C18—H180.9300
Pr1—O82.683 (2)C19—H190.9300
Pr1—N22.721 (3)C20—C211.509 (4)
Pr1—N12.765 (3)C21—C261.376 (5)
O1—C131.251 (4)C21—C221.389 (5)
O2—C131.253 (4)C22—C231.384 (5)
O2—Pr1ii2.387 (2)C22—H220.9300
O3—C171.359 (4)C23—C241.388 (5)
O3—H30.8200C23—H230.9300
O4—C201.257 (4)C24—C251.383 (5)
O5—C201.245 (4)C25—C261.386 (4)
O5—Pr1i2.395 (2)C25—H250.9300
O6—C241.360 (4)C26—H260.9300
O6—H60.8200C27—C281.385 (9)
O7—N71.267 (4)C27—H270.9300
O8—N71.277 (3)C28—C291.349 (9)
O8—Pr1i2.671 (2)C28—H280.9300
O9—N71.215 (4)C29—C301.392 (8)
N1—C11.318 (4)C29—H290.9300
N1—C121.361 (4)C30—C381.407 (6)
N2—C101.327 (4)C30—C311.463 (7)
N2—C111.357 (4)C31—C321.325 (8)
N3—C271.320 (6)C31—H310.9300
N3—C381.357 (5)C32—C331.407 (7)
N4—C361.314 (6)C32—H320.9300
N4—C371.344 (5)C33—C341.399 (7)
N5—C391.314 (7)C33—C371.418 (5)
N5—C501.350 (6)C34—C351.360 (9)
N6—C481.314 (6)C34—H340.9300
N6—C491.359 (6)C35—C361.387 (8)
C1—C21.401 (5)C35—H350.9300
C1—H10.9300C36—H360.9300
C2—C31.347 (6)C37—C381.444 (6)
C2—H20.9300C39—C401.403 (10)
C3—C41.399 (6)C39—H390.9300
C3—H3A0.9300C40—C411.350 (10)
C4—C121.413 (5)C40—H400.9300
C4—C51.436 (5)C41—C421.402 (10)
C5—C61.341 (6)C41—H410.9300
C5—H50.9300C42—C501.407 (6)
C6—C71.429 (5)C42—C431.429 (9)
C6—H6A0.9300C43—C441.340 (10)
C7—C81.391 (6)C43—H430.9300
C7—C111.418 (4)C44—C451.425 (8)
C8—C91.368 (6)C44—H440.9300
C8—H80.9300C45—C461.399 (8)
C9—C101.395 (5)C45—C491.416 (6)
C9—H90.9300C46—C471.364 (9)
C10—H100.9300C46—H460.9300
C11—C121.442 (5)C47—C481.397 (8)
C13—C141.503 (4)C47—H470.9300
C14—C191.383 (5)C48—H480.9300
C14—C151.388 (5)C49—C501.438 (7)
C15—C161.391 (5)
O2i—Pr1—O5ii147.50 (8)C17—C16—H16120.1
O2i—Pr1—O174.53 (8)C15—C16—H16120.1
O5ii—Pr1—O188.43 (8)O3—C17—C18117.4 (3)
O2i—Pr1—O499.18 (8)O3—C17—C16123.1 (3)
O5ii—Pr1—O479.01 (8)C18—C17—C16119.4 (3)
O1—Pr1—O4145.03 (8)C19—C18—C17120.2 (3)
O2i—Pr1—O775.83 (9)C19—C18—H18119.9
O5ii—Pr1—O7133.49 (8)C17—C18—H18119.9
O1—Pr1—O792.65 (8)C18—C19—C14121.2 (3)
O4—Pr1—O7119.63 (7)C18—C19—H19119.4
O2i—Pr1—O8ii77.31 (8)C14—C19—H19119.4
O5ii—Pr1—O8ii71.23 (8)O5—C20—O4124.8 (3)
O1—Pr1—O8ii72.90 (7)O5—C20—C21117.9 (3)
O4—Pr1—O8ii72.17 (7)O4—C20—C21117.3 (3)
O7—Pr1—O8ii152.09 (8)C26—C21—C22118.3 (3)
O2i—Pr1—O868.78 (7)C26—C21—C20120.9 (3)
O5ii—Pr1—O8138.38 (7)C22—C21—C20120.7 (3)
O1—Pr1—O8131.16 (8)C23—C22—C21120.4 (3)
O4—Pr1—O873.42 (7)C23—C22—H22119.8
O7—Pr1—O848.24 (7)C21—C22—H22119.8
O8ii—Pr1—O8126.12 (4)C22—C23—C24120.4 (3)
O2i—Pr1—N2136.17 (8)C22—C23—H23119.8
O5ii—Pr1—N275.24 (8)C24—C23—H23119.8
O1—Pr1—N2133.02 (8)O6—C24—C25123.2 (3)
O4—Pr1—N275.13 (8)O6—C24—C23117.3 (3)
O7—Pr1—N270.43 (8)C25—C24—C23119.5 (3)
O8ii—Pr1—N2136.62 (8)C24—C25—C26119.3 (3)
O8—Pr1—N267.99 (7)C24—C25—H25120.4
O2i—Pr1—N1128.07 (8)C26—C25—H25120.4
O5ii—Pr1—N169.41 (8)C21—C26—C25122.0 (3)
O1—Pr1—N172.78 (8)C21—C26—H26119.0
O4—Pr1—N1130.05 (8)C25—C26—H26119.0
O7—Pr1—N166.66 (8)N3—C27—C28123.0 (5)
O8ii—Pr1—N1127.56 (7)N3—C27—H27118.5
O8—Pr1—N1106.31 (7)C28—C27—H27118.5
N2—Pr1—N160.24 (8)C29—C28—C27120.1 (6)
C13—O1—Pr1145.7 (2)C29—C28—H28119.9
C13—O2—Pr1ii152.9 (2)C27—C28—H28119.9
C17—O3—H3109.5C28—C29—C30119.6 (5)
C20—O4—Pr1142.2 (2)C28—C29—H29120.2
C20—O5—Pr1i148.5 (2)C30—C29—H29120.2
C24—O6—H6109.5C29—C30—C38116.8 (5)
N7—O7—Pr1100.04 (17)C29—C30—C31125.3 (5)
N7—O8—Pr1i127.27 (19)C38—C30—C31117.9 (5)
N7—O8—Pr195.22 (16)C32—C31—C30122.0 (4)
Pr1i—O8—Pr1128.52 (8)C32—C31—H31119.0
C1—N1—C12117.8 (3)C30—C31—H31119.0
C1—N1—Pr1122.5 (2)C31—C32—C33121.8 (5)
C12—N1—Pr1119.0 (2)C31—C32—H32119.1
C10—N2—C11117.5 (3)C33—C32—H32119.1
C10—N2—Pr1120.8 (2)C34—C33—C32123.5 (4)
C11—N2—Pr1120.47 (19)C34—C33—C37117.6 (4)
C27—N3—C38117.2 (4)C32—C33—C37118.9 (5)
C36—N4—C37118.4 (4)C35—C34—C33120.1 (4)
C39—N5—C50117.6 (5)C35—C34—H34119.9
C48—N6—C49118.2 (4)C33—C34—H34119.9
O9—N7—O7121.7 (3)C34—C35—C36117.8 (5)
O9—N7—O8122.3 (3)C34—C35—H35121.1
O7—N7—O8115.9 (3)C36—C35—H35121.1
N1—C1—C2123.5 (3)N4—C36—C35124.5 (6)
N1—C1—H1118.2N4—C36—H36117.7
C2—C1—H1118.2C35—C36—H36117.7
C3—C2—C1119.2 (4)N4—C37—C33121.4 (4)
C3—C2—H2120.4N4—C37—C38118.3 (3)
C1—C2—H2120.4C33—C37—C38120.3 (4)
C2—C3—C4119.6 (3)N3—C38—C30123.3 (4)
C2—C3—H3A120.2N3—C38—C37117.6 (4)
C4—C3—H3A120.2C30—C38—C37119.1 (4)
C3—C4—C12118.0 (3)N5—C39—C40123.9 (6)
C3—C4—C5122.3 (3)N5—C39—H39118.0
C12—C4—C5119.7 (3)C40—C39—H39118.0
C6—C5—C4121.1 (3)C41—C40—C39118.2 (6)
C6—C5—H5119.4C41—C40—H40120.9
C4—C5—H5119.4C39—C40—H40120.9
C5—C6—C7120.9 (3)C40—C41—C42120.6 (6)
C5—C6—H6A119.6C40—C41—H41119.7
C7—C6—H6A119.6C42—C41—H41119.7
C8—C7—C11117.6 (3)C41—C42—C50116.6 (6)
C8—C7—C6122.2 (3)C41—C42—C43123.7 (6)
C11—C7—C6120.2 (3)C50—C42—C43119.7 (6)
C9—C8—C7119.8 (3)C44—C43—C42121.7 (5)
C9—C8—H8120.1C44—C43—H43119.1
C7—C8—H8120.1C42—C43—H43119.1
C8—C9—C10118.7 (4)C43—C44—C45121.0 (6)
C8—C9—H9120.6C43—C44—H44119.5
C10—C9—H9120.6C45—C44—H44119.5
N2—C10—C9123.8 (3)C46—C45—C49118.4 (5)
N2—C10—H10118.1C46—C45—C44122.9 (6)
C9—C10—H10118.1C49—C45—C44118.7 (6)
N2—C11—C7122.5 (3)C47—C46—C45119.9 (5)
N2—C11—C12118.8 (3)C47—C46—H46120.1
C7—C11—C12118.7 (3)C45—C46—H46120.1
N1—C12—C4121.8 (3)C46—C47—C48117.7 (6)
N1—C12—C11118.8 (3)C46—C47—H47121.1
C4—C12—C11119.4 (3)C48—C47—H47121.1
O1—C13—O2125.3 (3)N6—C48—C47124.7 (6)
O1—C13—C14117.5 (3)N6—C48—H48117.6
O2—C13—C14117.2 (3)C47—C48—H48117.6
C19—C14—C15118.5 (3)N6—C49—C45121.1 (5)
C19—C14—C13120.4 (3)N6—C49—C50118.3 (4)
C15—C14—C13121.0 (3)C45—C49—C50120.6 (4)
C14—C15—C16120.8 (3)N5—C50—C42123.0 (5)
C14—C15—H15119.6N5—C50—C49118.7 (4)
C16—C15—H15119.6C42—C50—C49118.2 (4)
C17—C16—C15119.8 (3)
O2i—Pr1—O1—C1387.7 (4)C3—C4—C12—N11.9 (5)
O5ii—Pr1—O1—C1364.3 (4)C5—C4—C12—N1178.3 (3)
O4—Pr1—O1—C133.9 (5)C3—C4—C12—C11177.0 (3)
O7—Pr1—O1—C13162.2 (4)C5—C4—C12—C112.8 (5)
O8ii—Pr1—O1—C136.5 (4)N2—C11—C12—N12.4 (4)
O8—Pr1—O1—C13129.9 (4)C7—C11—C12—N1178.8 (3)
N2—Pr1—O1—C13132.3 (4)N2—C11—C12—C4176.5 (3)
N1—Pr1—O1—C13133.2 (4)C7—C11—C12—C42.2 (5)
O2i—Pr1—O4—C2042.3 (3)Pr1—O1—C13—O222.6 (6)
O5ii—Pr1—O4—C20170.6 (3)Pr1—O1—C13—C14157.1 (3)
O1—Pr1—O4—C20118.4 (3)Pr1ii—O2—C13—O16.1 (7)
O7—Pr1—O4—C2036.5 (4)Pr1ii—O2—C13—C14173.6 (4)
O8ii—Pr1—O4—C20115.7 (3)O1—C13—C14—C19170.8 (3)
O8—Pr1—O4—C2022.2 (3)O2—C13—C14—C199.4 (5)
N2—Pr1—O4—C2093.2 (3)O1—C13—C14—C158.8 (5)
N1—Pr1—O4—C20119.8 (3)O2—C13—C14—C15171.0 (3)
O2i—Pr1—O7—N778.52 (19)C19—C14—C15—C160.9 (5)
O5ii—Pr1—O7—N7117.83 (18)C13—C14—C15—C16179.5 (3)
O1—Pr1—O7—N7151.84 (19)C14—C15—C16—C171.3 (6)
O4—Pr1—O7—N714.1 (2)C15—C16—C17—O3179.9 (4)
O8ii—Pr1—O7—N794.6 (2)C15—C16—C17—C180.3 (7)
O8—Pr1—O7—N74.48 (16)O3—C17—C18—C19178.7 (4)
N2—Pr1—O7—N773.06 (19)C16—C17—C18—C191.1 (7)
N1—Pr1—O7—N7138.2 (2)C17—C18—C19—C141.6 (7)
O2i—Pr1—O8—N794.08 (18)C15—C14—C19—C180.5 (6)
O5ii—Pr1—O8—N7108.21 (19)C13—C14—C19—C18179.1 (4)
O1—Pr1—O8—N750.1 (2)Pr1i—O5—C20—O457.3 (5)
O4—Pr1—O8—N7158.81 (18)Pr1i—O5—C20—C21121.8 (3)
O7—Pr1—O8—N74.39 (16)Pr1—O4—C20—O520.8 (5)
O8ii—Pr1—O8—N7148.99 (13)Pr1—O4—C20—C21158.3 (2)
N2—Pr1—O8—N778.51 (17)O5—C20—C21—C265.2 (4)
N1—Pr1—O8—N731.05 (18)O4—C20—C21—C26175.7 (3)
O2i—Pr1—O8—Pr1i54.12 (11)O5—C20—C21—C22171.6 (3)
O5ii—Pr1—O8—Pr1i103.59 (13)O4—C20—C21—C227.5 (4)
O1—Pr1—O8—Pr1i98.11 (13)C26—C21—C22—C230.6 (6)
O4—Pr1—O8—Pr1i52.99 (11)C20—C21—C22—C23177.4 (4)
O7—Pr1—O8—Pr1i143.81 (16)C21—C22—C23—C240.1 (7)
O8ii—Pr1—O8—Pr1i0.8 (2)C22—C23—C24—O6178.8 (4)
N2—Pr1—O8—Pr1i133.28 (13)C22—C23—C24—C250.1 (6)
N1—Pr1—O8—Pr1i179.25 (10)O6—C24—C25—C26179.6 (4)
O2i—Pr1—N1—C149.4 (3)C23—C24—C25—C261.0 (6)
O5ii—Pr1—N1—C198.8 (3)C22—C21—C26—C251.5 (5)
O1—Pr1—N1—C13.9 (3)C20—C21—C26—C25178.3 (3)
O4—Pr1—N1—C1153.2 (2)C24—C25—C26—C211.7 (5)
O7—Pr1—N1—C196.9 (3)C38—N3—C27—C281.0 (7)
O8ii—Pr1—N1—C155.1 (3)N3—C27—C28—C290.6 (9)
O8—Pr1—N1—C1125.0 (3)C27—C28—C29—C301.7 (9)
N2—Pr1—N1—C1176.9 (3)C28—C29—C30—C381.2 (7)
O2i—Pr1—N1—C12139.7 (2)C28—C29—C30—C31179.2 (5)
O5ii—Pr1—N1—C1272.0 (2)C29—C30—C31—C32178.0 (5)
O1—Pr1—N1—C12166.9 (2)C38—C30—C31—C322.3 (6)
O4—Pr1—N1—C1217.6 (3)C30—C31—C32—C330.1 (7)
O7—Pr1—N1—C1292.3 (2)C31—C32—C33—C34176.6 (4)
O8ii—Pr1—N1—C12115.8 (2)C31—C32—C33—C372.5 (6)
O8—Pr1—N1—C1264.2 (2)C32—C33—C34—C35178.6 (5)
N2—Pr1—N1—C1212.3 (2)C37—C33—C34—C350.5 (7)
O2i—Pr1—N2—C1063.6 (3)C33—C34—C35—C362.9 (9)
O5ii—Pr1—N2—C10106.5 (3)C37—N4—C36—C350.3 (9)
O1—Pr1—N2—C10179.9 (2)C34—C35—C36—N42.7 (11)
O4—Pr1—N2—C1024.2 (3)C36—N4—C37—C332.9 (6)
O7—Pr1—N2—C10105.4 (3)C36—N4—C37—C38176.4 (4)
O8ii—Pr1—N2—C1066.2 (3)C34—C33—C37—N42.6 (6)
O8—Pr1—N2—C1053.6 (3)C32—C33—C37—N4178.3 (4)
N1—Pr1—N2—C10179.1 (3)C34—C33—C37—C38176.7 (3)
O2i—Pr1—N2—C11129.3 (2)C32—C33—C37—C382.4 (5)
O5ii—Pr1—N2—C1160.6 (2)C27—N3—C38—C301.5 (6)
O1—Pr1—N2—C1112.8 (3)C27—N3—C38—C37177.0 (4)
O4—Pr1—N2—C11142.9 (2)C29—C30—C38—N30.5 (6)
O7—Pr1—N2—C1187.5 (2)C31—C30—C38—N3179.2 (3)
O8ii—Pr1—N2—C11100.9 (2)C29—C30—C38—C37178.0 (4)
O8—Pr1—N2—C11139.3 (2)C31—C30—C38—C372.3 (5)
N1—Pr1—N2—C1113.8 (2)N4—C37—C38—N30.7 (5)
Pr1—O7—N7—O9170.5 (3)C33—C37—C38—N3178.6 (3)
Pr1—O7—N7—O87.8 (3)N4—C37—C38—C30179.3 (3)
Pr1i—O8—N7—O940.3 (4)C33—C37—C38—C300.0 (5)
Pr1—O8—N7—O9170.9 (3)C50—N5—C39—C400.5 (9)
Pr1i—O8—N7—O7141.3 (2)N5—C39—C40—C411.9 (11)
Pr1—O8—N7—O77.5 (3)C39—C40—C41—C421.2 (10)
C12—N1—C1—C20.6 (5)C40—C41—C42—C500.7 (8)
Pr1—N1—C1—C2171.5 (3)C40—C41—C42—C43179.0 (6)
N1—C1—C2—C31.3 (6)C41—C42—C43—C44179.7 (5)
C1—C2—C3—C40.4 (6)C50—C42—C43—C440.1 (7)
C2—C3—C4—C121.1 (6)C42—C43—C44—C452.3 (8)
C2—C3—C4—C5179.1 (4)C43—C44—C45—C46176.7 (5)
C3—C4—C5—C6178.3 (4)C43—C44—C45—C491.8 (7)
C12—C4—C5—C61.5 (6)C49—C45—C46—C471.8 (6)
C4—C5—C6—C70.4 (6)C44—C45—C46—C47176.7 (4)
C5—C6—C7—C8178.6 (4)C45—C46—C47—C482.2 (7)
C5—C6—C7—C111.0 (6)C49—N6—C48—C470.7 (7)
C11—C7—C8—C91.9 (6)C46—C47—C48—N61.0 (7)
C6—C7—C8—C9177.7 (4)C48—N6—C49—C451.1 (6)
C7—C8—C9—C100.3 (6)C48—N6—C49—C50178.4 (4)
C11—N2—C10—C93.0 (5)C46—C45—C49—N60.1 (6)
Pr1—N2—C10—C9164.5 (3)C44—C45—C49—N6178.5 (4)
C8—C9—C10—N22.3 (6)C46—C45—C49—C50179.6 (4)
C10—N2—C11—C71.2 (5)C44—C45—C49—C501.0 (6)
Pr1—N2—C11—C7166.4 (2)C39—N5—C50—C421.6 (7)
C10—N2—C11—C12177.6 (3)C39—N5—C50—C49178.1 (4)
Pr1—N2—C11—C1214.9 (4)C41—C42—C50—N52.2 (6)
C8—C7—C11—N21.2 (5)C43—C42—C50—N5177.4 (4)
C6—C7—C11—N2178.4 (3)C41—C42—C50—C49177.5 (4)
C8—C7—C11—C12179.9 (3)C43—C42—C50—C492.8 (6)
C6—C7—C11—C120.4 (5)N6—C49—C50—N53.5 (5)
C1—N1—C12—C41.1 (5)C45—C49—C50—N5177.0 (3)
Pr1—N1—C12—C4170.2 (2)N6—C49—C50—C42176.3 (3)
C1—N1—C12—C11177.9 (3)C45—C49—C50—C423.3 (5)
Pr1—N1—C12—C1110.9 (4)
Symmetry codes: (i) x, y+3/2, z1/2; (ii) x, y+3/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6···N4iii0.822.072.851 (4)158
O3—H3···N6iv0.822.042.782 (5)150
Symmetry codes: (iii) x+1, y+3/2, z1/2; (iv) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formula[Pr(C7H5O3)2(NO3)(C12H8N2)]·2C12H8N2
Mr1017.75
Crystal system, space groupMonoclinic, P21/c
Temperature (K)291
a, b, c (Å)21.5625 (2), 23.4621 (2), 8.6030 (1)
β (°) 98.899 (1)
V3)4299.88 (7)
Z4
Radiation typeCu Kα
µ (mm1)9.27
Crystal size (mm)0.40 × 0.33 × 0.30
Data collection
DiffractometerOxford Diffraction Gemini S Ultra
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2006)
Tmin, Tmax0.119, 0.167
No. of measured, independent and
observed [I > 2σ(I)] reflections
13264, 7308, 6794
Rint0.029
(sin θ/λ)max1)0.588
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.092, 1.06
No. of reflections7308
No. of parameters606
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.74, 1.31

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6···N4i0.822.072.851 (4)158
O3—H3···N6ii0.822.042.782 (5)150
Symmetry codes: (i) x+1, y+3/2, z1/2; (ii) x+1, y+1, z+1.
 

Acknowledgements

The authors thank Dr H. P. Xiao for help with the experiments.

References

First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals
First citationOxford Diffraction (2006). CrysAlis PRO, CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationZhou, Y. X., Shen, X. Q., Zhang, H. Y., Du, C. X., Wu, B. L. & Hou, H. W. (2008). J. Coord. Chem. E61, 3981–3992.  Web of Science CSD CrossRef
First citationZhu, Y.-M., Feng, P.-P., Yang, Y.-Y. & Ng, S. W. (2010). Acta Cryst. E66, m54–m55.  Web of Science CSD CrossRef IUCr Journals

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