metal-organic compounds
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
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.
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; 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.
Supporting information
10.1107/S1600536812029911/fj2550sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812029911/fj2550Isup2.hkl
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.
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).
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell
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).[Pr(C7H5O3)2(NO3)(C12H8N2)]·2C12H8N2 | F(000) = 2056 |
Mr = 1017.75 | Dx = 1.572 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
Hall symbol: -P 2ybc | Cell parameters from 9626 reflections |
a = 21.5625 (2) Å | θ = 1.9–67.4° |
b = 23.4621 (2) Å | µ = 9.27 mm−1 |
c = 8.6030 (1) Å | T = 291 K |
β = 98.899 (1)° | Needle, white |
V = 4299.88 (7) Å3 | 0.40 × 0.33 × 0.30 mm |
Z = 4 |
Oxford Diffraction Gemini S Ultra diffractometer | 7308 independent reflections |
Radiation source: Enhance Ultra (Cu) X-ray Source | 6794 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.029 |
Detector resolution: 15.9149 pixels mm-1 | θmax = 65.1°, θmin = 2.1° |
ω scans | h = −25→25 |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006) | k = −27→16 |
Tmin = 0.119, Tmax = 0.167 | l = −9→10 |
13264 measured reflections |
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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.092 | H-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 parameters | Δρmax = 0.74 e Å−3 |
0 restraints | Δρmin = −1.31 e Å−3 |
[Pr(C7H5O3)2(NO3)(C12H8N2)]·2C12H8N2 | V = 4299.88 (7) Å3 |
Mr = 1017.75 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 21.5625 (2) Å | µ = 9.27 mm−1 |
b = 23.4621 (2) Å | T = 291 K |
c = 8.6030 (1) Å | 0.40 × 0.33 × 0.30 mm |
β = 98.899 (1)° |
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 = 0.167 | Rint = 0.029 |
13264 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.092 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.74 e Å−3 |
7308 reflections | Δρmin = −1.31 e Å−3 |
606 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Pr1 | 0.911380 (7) | 0.703539 (6) | 0.660845 (17) | 0.02673 (8) | |
O1 | 0.82724 (10) | 0.69075 (10) | 0.8105 (3) | 0.0402 (5) | |
O2 | 0.82646 (10) | 0.74065 (11) | 1.0300 (3) | 0.0446 (5) | |
O3 | 0.54691 (13) | 0.65243 (17) | 0.9284 (4) | 0.0741 (10) | |
H3 | 0.5307 | 0.6376 | 0.8457 | 0.111* | |
O4 | 0.99741 (10) | 0.76381 (10) | 0.6186 (3) | 0.0388 (5) | |
O5 | 0.98379 (10) | 0.81352 (10) | 0.3967 (3) | 0.0393 (5) | |
O6 | 1.27882 (11) | 0.83426 (15) | 0.5929 (3) | 0.0609 (8) | |
H6 | 1.2891 | 0.8501 | 0.5159 | 0.091* | |
O7 | 0.85863 (12) | 0.63832 (10) | 0.4358 (3) | 0.0473 (6) | |
O8 | 0.91180 (11) | 0.70593 (8) | 0.3492 (3) | 0.0344 (5) | |
O9 | 0.87386 (16) | 0.63694 (11) | 0.1925 (3) | 0.0620 (8) | |
N1 | 0.91051 (12) | 0.58977 (11) | 0.7443 (3) | 0.0372 (6) | |
N2 | 0.99832 (12) | 0.63129 (11) | 0.5726 (3) | 0.0360 (6) | |
N3 | 0.29434 (16) | 0.53994 (16) | 0.9226 (4) | 0.0588 (8) | |
N4 | 0.32464 (19) | 0.64182 (15) | 0.8063 (4) | 0.0628 (9) | |
N5 | 0.50294 (18) | 0.33752 (18) | 0.4667 (5) | 0.0684 (10) | |
N6 | 0.52702 (16) | 0.42317 (16) | 0.2691 (4) | 0.0608 (9) | |
N7 | 0.88073 (13) | 0.65978 (11) | 0.3208 (3) | 0.0382 (6) | |
C1 | 0.86749 (17) | 0.56790 (15) | 0.8203 (4) | 0.0452 (8) | |
H1 | 0.8333 | 0.5905 | 0.8339 | 0.054* | |
C2 | 0.8705 (2) | 0.51245 (17) | 0.8815 (5) | 0.0570 (10) | |
H2 | 0.8385 | 0.4987 | 0.9324 | 0.068* | |
C3 | 0.9202 (2) | 0.47938 (16) | 0.8658 (4) | 0.0560 (10) | |
H3A | 0.9230 | 0.4426 | 0.9064 | 0.067* | |
C4 | 0.96762 (18) | 0.50076 (15) | 0.7881 (4) | 0.0455 (8) | |
C5 | 1.0222 (2) | 0.46801 (16) | 0.7694 (4) | 0.0542 (9) | |
H5 | 1.0271 | 0.4316 | 0.8125 | 0.065* | |
C6 | 1.06627 (19) | 0.48895 (16) | 0.6909 (5) | 0.0532 (9) | |
H6A | 1.1014 | 0.4670 | 0.6810 | 0.064* | |
C7 | 1.05998 (16) | 0.54452 (15) | 0.6224 (4) | 0.0450 (8) | |
C8 | 1.10422 (18) | 0.56691 (18) | 0.5375 (5) | 0.0554 (10) | |
H8 | 1.1401 | 0.5461 | 0.5269 | 0.066* | |
C9 | 1.09484 (17) | 0.61956 (18) | 0.4694 (5) | 0.0541 (9) | |
H9 | 1.1240 | 0.6349 | 0.4119 | 0.065* | |
C10 | 1.04075 (16) | 0.64978 (15) | 0.4880 (4) | 0.0440 (8) | |
H10 | 1.0340 | 0.6849 | 0.4382 | 0.053* | |
C11 | 1.00721 (15) | 0.57883 (13) | 0.6386 (4) | 0.0360 (7) | |
C12 | 0.96066 (15) | 0.55657 (13) | 0.7261 (4) | 0.0368 (7) | |
C13 | 0.80099 (15) | 0.70958 (12) | 0.9199 (4) | 0.0322 (7) | |
C14 | 0.73337 (15) | 0.69387 (13) | 0.9191 (4) | 0.0334 (6) | |
C15 | 0.69901 (15) | 0.66640 (15) | 0.7909 (4) | 0.0393 (7) | |
H15 | 0.7182 | 0.6573 | 0.7044 | 0.047* | |
C16 | 0.63630 (16) | 0.65238 (16) | 0.7902 (4) | 0.0470 (8) | |
H16 | 0.6135 | 0.6347 | 0.7028 | 0.056* | |
C17 | 0.60788 (16) | 0.66489 (18) | 0.9204 (5) | 0.0517 (9) | |
C18 | 0.64241 (19) | 0.6915 (2) | 1.0494 (5) | 0.0602 (11) | |
H18 | 0.6239 | 0.6994 | 1.1377 | 0.072* | |
C19 | 0.70412 (18) | 0.70630 (15) | 1.0472 (5) | 0.0475 (9) | |
H19 | 0.7265 | 0.7250 | 1.1335 | 0.057* | |
C20 | 1.01715 (15) | 0.79388 (12) | 0.5157 (4) | 0.0317 (7) | |
C21 | 1.08667 (14) | 0.80619 (13) | 0.5374 (4) | 0.0312 (6) | |
C22 | 1.12756 (16) | 0.77961 (17) | 0.6560 (4) | 0.0457 (8) | |
H22 | 1.1119 | 0.7551 | 0.7255 | 0.055* | |
C23 | 1.19154 (18) | 0.78935 (18) | 0.6716 (5) | 0.0543 (10) | |
H23 | 1.2185 | 0.7713 | 0.7513 | 0.065* | |
C24 | 1.21567 (15) | 0.82586 (16) | 0.5690 (4) | 0.0432 (8) | |
C25 | 1.17529 (15) | 0.85264 (15) | 0.4508 (4) | 0.0409 (7) | |
H25 | 1.1908 | 0.8776 | 0.3822 | 0.049* | |
C26 | 1.11146 (15) | 0.84181 (14) | 0.4357 (4) | 0.0371 (7) | |
H26 | 1.0846 | 0.8591 | 0.3545 | 0.045* | |
C27 | 0.2817 (2) | 0.4893 (2) | 0.9770 (7) | 0.0762 (14) | |
H27 | 0.2878 | 0.4838 | 1.0853 | 0.091* | |
C28 | 0.2599 (3) | 0.4442 (3) | 0.8801 (10) | 0.097 (2) | |
H28 | 0.2521 | 0.4092 | 0.9237 | 0.116* | |
C29 | 0.2501 (2) | 0.4509 (3) | 0.7224 (9) | 0.0909 (18) | |
H29 | 0.2343 | 0.4209 | 0.6573 | 0.109* | |
C30 | 0.26354 (17) | 0.5030 (2) | 0.6578 (6) | 0.0656 (12) | |
C31 | 0.2559 (2) | 0.5159 (3) | 0.4895 (6) | 0.0795 (17) | |
H31 | 0.2396 | 0.4880 | 0.4178 | 0.095* | |
C32 | 0.2714 (2) | 0.5660 (3) | 0.4363 (6) | 0.0729 (14) | |
H32 | 0.2657 | 0.5724 | 0.3283 | 0.087* | |
C33 | 0.29633 (18) | 0.6099 (2) | 0.5385 (5) | 0.0578 (11) | |
C34 | 0.3163 (2) | 0.6624 (2) | 0.4868 (6) | 0.0741 (14) | |
H34 | 0.3126 | 0.6700 | 0.3796 | 0.089* | |
C35 | 0.3411 (4) | 0.7024 (2) | 0.5929 (8) | 0.093 (2) | |
H35 | 0.3564 | 0.7368 | 0.5604 | 0.112* | |
C36 | 0.3430 (3) | 0.6902 (2) | 0.7513 (7) | 0.0863 (17) | |
H36 | 0.3583 | 0.7182 | 0.8237 | 0.104* | |
C37 | 0.30263 (17) | 0.60086 (18) | 0.7031 (4) | 0.0505 (9) | |
C38 | 0.28600 (16) | 0.54654 (18) | 0.7640 (5) | 0.0508 (9) | |
C39 | 0.4948 (3) | 0.2955 (2) | 0.5625 (8) | 0.0887 (18) | |
H39 | 0.4729 | 0.2635 | 0.5204 | 0.106* | |
C40 | 0.5173 (4) | 0.2960 (3) | 0.7245 (9) | 0.108 (3) | |
H40 | 0.5115 | 0.2648 | 0.7873 | 0.130* | |
C41 | 0.5475 (3) | 0.3430 (4) | 0.7867 (7) | 0.103 (2) | |
H41 | 0.5621 | 0.3446 | 0.8942 | 0.124* | |
C42 | 0.5571 (2) | 0.3895 (3) | 0.6909 (6) | 0.0754 (15) | |
C43 | 0.5878 (2) | 0.4410 (4) | 0.7490 (7) | 0.095 (2) | |
H43 | 0.6026 | 0.4443 | 0.8560 | 0.113* | |
C44 | 0.5958 (2) | 0.4845 (3) | 0.6533 (8) | 0.092 (2) | |
H44 | 0.6146 | 0.5179 | 0.6955 | 0.110* | |
C45 | 0.57586 (18) | 0.4804 (2) | 0.4878 (7) | 0.0728 (14) | |
C46 | 0.5861 (2) | 0.5236 (2) | 0.3827 (9) | 0.0855 (17) | |
H46 | 0.6047 | 0.5577 | 0.4203 | 0.103* | |
C47 | 0.5686 (2) | 0.5157 (3) | 0.2249 (10) | 0.0897 (18) | |
H47 | 0.5763 | 0.5434 | 0.1529 | 0.108* | |
C48 | 0.5387 (2) | 0.4646 (2) | 0.1750 (7) | 0.0743 (13) | |
H48 | 0.5262 | 0.4595 | 0.0676 | 0.089* | |
C49 | 0.54567 (17) | 0.42982 (19) | 0.4263 (5) | 0.0579 (10) | |
C50 | 0.53442 (17) | 0.3839 (2) | 0.5292 (5) | 0.0589 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Pr1 | 0.02430 (11) | 0.03072 (12) | 0.02603 (11) | 0.00020 (5) | 0.00666 (7) | −0.00008 (5) |
O1 | 0.0344 (11) | 0.0491 (12) | 0.0408 (13) | −0.0055 (10) | 0.0173 (10) | −0.0017 (10) |
O2 | 0.0381 (12) | 0.0556 (14) | 0.0408 (13) | −0.0136 (11) | 0.0080 (10) | −0.0071 (11) |
O3 | 0.0370 (14) | 0.111 (3) | 0.078 (2) | −0.0256 (15) | 0.0191 (14) | −0.0280 (19) |
O4 | 0.0333 (10) | 0.0483 (13) | 0.0367 (12) | −0.0096 (9) | 0.0113 (9) | 0.0016 (10) |
O5 | 0.0331 (11) | 0.0512 (13) | 0.0323 (11) | −0.0029 (10) | 0.0008 (9) | 0.0005 (10) |
O6 | 0.0308 (12) | 0.102 (2) | 0.0493 (15) | −0.0079 (13) | 0.0055 (11) | 0.0225 (15) |
O7 | 0.0578 (14) | 0.0437 (13) | 0.0404 (13) | −0.0166 (11) | 0.0074 (11) | 0.0008 (10) |
O8 | 0.0381 (12) | 0.0333 (12) | 0.0330 (12) | −0.0010 (8) | 0.0090 (10) | 0.0008 (8) |
O9 | 0.100 (2) | 0.0472 (14) | 0.0361 (13) | 0.0003 (15) | 0.0019 (14) | −0.0124 (11) |
N1 | 0.0403 (14) | 0.0380 (14) | 0.0334 (13) | 0.0007 (11) | 0.0057 (11) | −0.0008 (11) |
N2 | 0.0361 (13) | 0.0383 (14) | 0.0349 (13) | 0.0030 (11) | 0.0101 (11) | −0.0013 (11) |
N3 | 0.0498 (18) | 0.071 (2) | 0.057 (2) | 0.0027 (16) | 0.0108 (15) | 0.0065 (17) |
N4 | 0.085 (3) | 0.055 (2) | 0.0530 (19) | 0.0041 (18) | 0.0268 (19) | −0.0061 (16) |
N5 | 0.059 (2) | 0.086 (3) | 0.060 (2) | −0.004 (2) | 0.0087 (18) | −0.003 (2) |
N6 | 0.0463 (17) | 0.068 (2) | 0.066 (2) | 0.0057 (16) | 0.0029 (16) | −0.0012 (18) |
N7 | 0.0494 (15) | 0.0292 (13) | 0.0352 (15) | −0.0003 (12) | 0.0043 (12) | −0.0014 (11) |
C1 | 0.0495 (19) | 0.0416 (18) | 0.0469 (19) | −0.0023 (15) | 0.0156 (16) | 0.0044 (15) |
C2 | 0.071 (3) | 0.052 (2) | 0.052 (2) | −0.0089 (19) | 0.023 (2) | 0.0068 (17) |
C3 | 0.083 (3) | 0.0395 (18) | 0.046 (2) | 0.0005 (19) | 0.012 (2) | 0.0078 (16) |
C4 | 0.062 (2) | 0.0403 (17) | 0.0318 (16) | 0.0057 (16) | 0.0014 (15) | 0.0013 (14) |
C5 | 0.077 (3) | 0.0399 (18) | 0.0433 (19) | 0.0168 (19) | 0.0006 (19) | 0.0007 (15) |
C6 | 0.059 (2) | 0.047 (2) | 0.051 (2) | 0.0202 (17) | 0.0000 (18) | −0.0073 (17) |
C7 | 0.0457 (18) | 0.0481 (19) | 0.0394 (17) | 0.0121 (15) | 0.0011 (15) | −0.0086 (15) |
C8 | 0.0423 (18) | 0.063 (2) | 0.061 (2) | 0.0181 (17) | 0.0112 (17) | −0.0090 (19) |
C9 | 0.0437 (19) | 0.062 (2) | 0.062 (2) | 0.0063 (17) | 0.0236 (18) | −0.0072 (19) |
C10 | 0.0434 (18) | 0.0438 (18) | 0.0481 (19) | 0.0003 (14) | 0.0171 (15) | −0.0040 (15) |
C11 | 0.0368 (15) | 0.0385 (17) | 0.0315 (15) | 0.0068 (13) | 0.0013 (12) | −0.0072 (13) |
C12 | 0.0434 (16) | 0.0364 (16) | 0.0294 (15) | 0.0030 (13) | 0.0026 (13) | −0.0046 (12) |
C13 | 0.0292 (15) | 0.0345 (15) | 0.0343 (17) | −0.0015 (11) | 0.0088 (13) | 0.0078 (12) |
C14 | 0.0297 (15) | 0.0376 (15) | 0.0339 (16) | −0.0031 (12) | 0.0080 (13) | −0.0012 (12) |
C15 | 0.0346 (15) | 0.0486 (18) | 0.0353 (16) | −0.0042 (14) | 0.0071 (13) | −0.0068 (14) |
C16 | 0.0372 (17) | 0.057 (2) | 0.0459 (19) | −0.0091 (15) | 0.0035 (15) | −0.0128 (16) |
C17 | 0.0328 (16) | 0.066 (2) | 0.057 (2) | −0.0124 (16) | 0.0119 (16) | −0.0113 (18) |
C18 | 0.043 (2) | 0.087 (3) | 0.056 (2) | −0.013 (2) | 0.0251 (19) | −0.024 (2) |
C19 | 0.0377 (19) | 0.065 (2) | 0.041 (2) | −0.0108 (15) | 0.0098 (16) | −0.0185 (15) |
C20 | 0.0310 (16) | 0.0336 (16) | 0.0319 (16) | −0.0030 (11) | 0.0090 (13) | −0.0083 (12) |
C21 | 0.0299 (15) | 0.0368 (15) | 0.0277 (15) | −0.0026 (12) | 0.0064 (12) | −0.0029 (12) |
C22 | 0.0383 (17) | 0.058 (2) | 0.0409 (18) | −0.0041 (16) | 0.0072 (15) | 0.0152 (17) |
C23 | 0.0362 (19) | 0.079 (3) | 0.047 (2) | −0.0011 (17) | 0.0010 (16) | 0.0241 (18) |
C24 | 0.0317 (15) | 0.059 (2) | 0.0392 (17) | −0.0079 (15) | 0.0059 (13) | 0.0031 (15) |
C25 | 0.0370 (16) | 0.0492 (19) | 0.0370 (17) | −0.0066 (14) | 0.0071 (14) | 0.0091 (14) |
C26 | 0.0331 (15) | 0.0425 (17) | 0.0355 (16) | −0.0029 (13) | 0.0047 (13) | 0.0047 (13) |
C27 | 0.061 (3) | 0.077 (3) | 0.092 (4) | −0.006 (2) | 0.016 (3) | 0.024 (3) |
C28 | 0.065 (3) | 0.074 (4) | 0.154 (6) | −0.010 (3) | 0.026 (4) | 0.021 (4) |
C29 | 0.055 (3) | 0.084 (4) | 0.134 (5) | −0.019 (3) | 0.014 (3) | −0.034 (4) |
C30 | 0.0308 (17) | 0.077 (3) | 0.089 (3) | −0.0004 (19) | 0.0083 (19) | −0.024 (2) |
C31 | 0.040 (2) | 0.117 (5) | 0.078 (3) | 0.006 (2) | −0.002 (2) | −0.049 (3) |
C32 | 0.045 (2) | 0.118 (4) | 0.055 (3) | 0.015 (3) | 0.0059 (19) | −0.018 (3) |
C33 | 0.0412 (19) | 0.088 (3) | 0.046 (2) | 0.021 (2) | 0.0110 (16) | −0.002 (2) |
C34 | 0.072 (3) | 0.099 (4) | 0.056 (3) | 0.028 (3) | 0.026 (2) | 0.023 (3) |
C35 | 0.133 (6) | 0.070 (4) | 0.086 (4) | 0.017 (3) | 0.047 (4) | 0.018 (3) |
C36 | 0.130 (5) | 0.056 (3) | 0.082 (4) | 0.001 (3) | 0.047 (4) | −0.002 (3) |
C37 | 0.0444 (18) | 0.067 (2) | 0.0424 (19) | 0.0175 (17) | 0.0140 (15) | 0.0004 (17) |
C38 | 0.0319 (16) | 0.066 (2) | 0.056 (2) | 0.0061 (16) | 0.0088 (15) | −0.0082 (18) |
C39 | 0.088 (4) | 0.094 (4) | 0.089 (4) | −0.003 (3) | 0.029 (4) | 0.014 (3) |
C40 | 0.112 (6) | 0.137 (7) | 0.083 (5) | 0.021 (4) | 0.039 (4) | 0.035 (4) |
C41 | 0.084 (4) | 0.169 (7) | 0.060 (3) | 0.034 (4) | 0.019 (3) | −0.001 (4) |
C42 | 0.047 (2) | 0.124 (5) | 0.056 (3) | 0.020 (3) | 0.011 (2) | −0.017 (3) |
C43 | 0.053 (3) | 0.157 (6) | 0.073 (4) | 0.010 (3) | 0.006 (2) | −0.056 (4) |
C44 | 0.050 (3) | 0.122 (5) | 0.105 (4) | 0.000 (3) | 0.011 (3) | −0.061 (4) |
C45 | 0.0330 (19) | 0.081 (3) | 0.103 (4) | 0.012 (2) | 0.008 (2) | −0.037 (3) |
C46 | 0.048 (3) | 0.061 (3) | 0.150 (6) | 0.005 (2) | 0.024 (3) | −0.013 (4) |
C47 | 0.050 (3) | 0.082 (4) | 0.140 (6) | 0.013 (2) | 0.023 (3) | 0.022 (4) |
C48 | 0.054 (2) | 0.077 (3) | 0.092 (4) | 0.007 (2) | 0.009 (2) | 0.015 (3) |
C49 | 0.0313 (16) | 0.071 (3) | 0.070 (3) | 0.0110 (17) | 0.0049 (17) | −0.016 (2) |
C50 | 0.0372 (18) | 0.087 (3) | 0.053 (2) | 0.0113 (19) | 0.0060 (16) | −0.011 (2) |
Pr1—O2i | 2.387 (2) | C15—H15 | 0.9300 |
Pr1—O5ii | 2.395 (2) | C16—C17 | 1.389 (5) |
Pr1—O1 | 2.400 (2) | C16—H16 | 0.9300 |
Pr1—O4 | 2.404 (2) | C17—C18 | 1.385 (6) |
Pr1—O7 | 2.589 (2) | C18—C19 | 1.378 (5) |
Pr1—O8ii | 2.671 (2) | C18—H18 | 0.9300 |
Pr1—O8 | 2.683 (2) | C19—H19 | 0.9300 |
Pr1—N2 | 2.721 (3) | C20—C21 | 1.509 (4) |
Pr1—N1 | 2.765 (3) | C21—C26 | 1.376 (5) |
O1—C13 | 1.251 (4) | C21—C22 | 1.389 (5) |
O2—C13 | 1.253 (4) | C22—C23 | 1.384 (5) |
O2—Pr1ii | 2.387 (2) | C22—H22 | 0.9300 |
O3—C17 | 1.359 (4) | C23—C24 | 1.388 (5) |
O3—H3 | 0.8200 | C23—H23 | 0.9300 |
O4—C20 | 1.257 (4) | C24—C25 | 1.383 (5) |
O5—C20 | 1.245 (4) | C25—C26 | 1.386 (4) |
O5—Pr1i | 2.395 (2) | C25—H25 | 0.9300 |
O6—C24 | 1.360 (4) | C26—H26 | 0.9300 |
O6—H6 | 0.8200 | C27—C28 | 1.385 (9) |
O7—N7 | 1.267 (4) | C27—H27 | 0.9300 |
O8—N7 | 1.277 (3) | C28—C29 | 1.349 (9) |
O8—Pr1i | 2.671 (2) | C28—H28 | 0.9300 |
O9—N7 | 1.215 (4) | C29—C30 | 1.392 (8) |
N1—C1 | 1.318 (4) | C29—H29 | 0.9300 |
N1—C12 | 1.361 (4) | C30—C38 | 1.407 (6) |
N2—C10 | 1.327 (4) | C30—C31 | 1.463 (7) |
N2—C11 | 1.357 (4) | C31—C32 | 1.325 (8) |
N3—C27 | 1.320 (6) | C31—H31 | 0.9300 |
N3—C38 | 1.357 (5) | C32—C33 | 1.407 (7) |
N4—C36 | 1.314 (6) | C32—H32 | 0.9300 |
N4—C37 | 1.344 (5) | C33—C34 | 1.399 (7) |
N5—C39 | 1.314 (7) | C33—C37 | 1.418 (5) |
N5—C50 | 1.350 (6) | C34—C35 | 1.360 (9) |
N6—C48 | 1.314 (6) | C34—H34 | 0.9300 |
N6—C49 | 1.359 (6) | C35—C36 | 1.387 (8) |
C1—C2 | 1.401 (5) | C35—H35 | 0.9300 |
C1—H1 | 0.9300 | C36—H36 | 0.9300 |
C2—C3 | 1.347 (6) | C37—C38 | 1.444 (6) |
C2—H2 | 0.9300 | C39—C40 | 1.403 (10) |
C3—C4 | 1.399 (6) | C39—H39 | 0.9300 |
C3—H3A | 0.9300 | C40—C41 | 1.350 (10) |
C4—C12 | 1.413 (5) | C40—H40 | 0.9300 |
C4—C5 | 1.436 (5) | C41—C42 | 1.402 (10) |
C5—C6 | 1.341 (6) | C41—H41 | 0.9300 |
C5—H5 | 0.9300 | C42—C50 | 1.407 (6) |
C6—C7 | 1.429 (5) | C42—C43 | 1.429 (9) |
C6—H6A | 0.9300 | C43—C44 | 1.340 (10) |
C7—C8 | 1.391 (6) | C43—H43 | 0.9300 |
C7—C11 | 1.418 (4) | C44—C45 | 1.425 (8) |
C8—C9 | 1.368 (6) | C44—H44 | 0.9300 |
C8—H8 | 0.9300 | C45—C46 | 1.399 (8) |
C9—C10 | 1.395 (5) | C45—C49 | 1.416 (6) |
C9—H9 | 0.9300 | C46—C47 | 1.364 (9) |
C10—H10 | 0.9300 | C46—H46 | 0.9300 |
C11—C12 | 1.442 (5) | C47—C48 | 1.397 (8) |
C13—C14 | 1.503 (4) | C47—H47 | 0.9300 |
C14—C19 | 1.383 (5) | C48—H48 | 0.9300 |
C14—C15 | 1.388 (5) | C49—C50 | 1.438 (7) |
C15—C16 | 1.391 (5) | ||
O2i—Pr1—O5ii | 147.50 (8) | C17—C16—H16 | 120.1 |
O2i—Pr1—O1 | 74.53 (8) | C15—C16—H16 | 120.1 |
O5ii—Pr1—O1 | 88.43 (8) | O3—C17—C18 | 117.4 (3) |
O2i—Pr1—O4 | 99.18 (8) | O3—C17—C16 | 123.1 (3) |
O5ii—Pr1—O4 | 79.01 (8) | C18—C17—C16 | 119.4 (3) |
O1—Pr1—O4 | 145.03 (8) | C19—C18—C17 | 120.2 (3) |
O2i—Pr1—O7 | 75.83 (9) | C19—C18—H18 | 119.9 |
O5ii—Pr1—O7 | 133.49 (8) | C17—C18—H18 | 119.9 |
O1—Pr1—O7 | 92.65 (8) | C18—C19—C14 | 121.2 (3) |
O4—Pr1—O7 | 119.63 (7) | C18—C19—H19 | 119.4 |
O2i—Pr1—O8ii | 77.31 (8) | C14—C19—H19 | 119.4 |
O5ii—Pr1—O8ii | 71.23 (8) | O5—C20—O4 | 124.8 (3) |
O1—Pr1—O8ii | 72.90 (7) | O5—C20—C21 | 117.9 (3) |
O4—Pr1—O8ii | 72.17 (7) | O4—C20—C21 | 117.3 (3) |
O7—Pr1—O8ii | 152.09 (8) | C26—C21—C22 | 118.3 (3) |
O2i—Pr1—O8 | 68.78 (7) | C26—C21—C20 | 120.9 (3) |
O5ii—Pr1—O8 | 138.38 (7) | C22—C21—C20 | 120.7 (3) |
O1—Pr1—O8 | 131.16 (8) | C23—C22—C21 | 120.4 (3) |
O4—Pr1—O8 | 73.42 (7) | C23—C22—H22 | 119.8 |
O7—Pr1—O8 | 48.24 (7) | C21—C22—H22 | 119.8 |
O8ii—Pr1—O8 | 126.12 (4) | C22—C23—C24 | 120.4 (3) |
O2i—Pr1—N2 | 136.17 (8) | C22—C23—H23 | 119.8 |
O5ii—Pr1—N2 | 75.24 (8) | C24—C23—H23 | 119.8 |
O1—Pr1—N2 | 133.02 (8) | O6—C24—C25 | 123.2 (3) |
O4—Pr1—N2 | 75.13 (8) | O6—C24—C23 | 117.3 (3) |
O7—Pr1—N2 | 70.43 (8) | C25—C24—C23 | 119.5 (3) |
O8ii—Pr1—N2 | 136.62 (8) | C24—C25—C26 | 119.3 (3) |
O8—Pr1—N2 | 67.99 (7) | C24—C25—H25 | 120.4 |
O2i—Pr1—N1 | 128.07 (8) | C26—C25—H25 | 120.4 |
O5ii—Pr1—N1 | 69.41 (8) | C21—C26—C25 | 122.0 (3) |
O1—Pr1—N1 | 72.78 (8) | C21—C26—H26 | 119.0 |
O4—Pr1—N1 | 130.05 (8) | C25—C26—H26 | 119.0 |
O7—Pr1—N1 | 66.66 (8) | N3—C27—C28 | 123.0 (5) |
O8ii—Pr1—N1 | 127.56 (7) | N3—C27—H27 | 118.5 |
O8—Pr1—N1 | 106.31 (7) | C28—C27—H27 | 118.5 |
N2—Pr1—N1 | 60.24 (8) | C29—C28—C27 | 120.1 (6) |
C13—O1—Pr1 | 145.7 (2) | C29—C28—H28 | 119.9 |
C13—O2—Pr1ii | 152.9 (2) | C27—C28—H28 | 119.9 |
C17—O3—H3 | 109.5 | C28—C29—C30 | 119.6 (5) |
C20—O4—Pr1 | 142.2 (2) | C28—C29—H29 | 120.2 |
C20—O5—Pr1i | 148.5 (2) | C30—C29—H29 | 120.2 |
C24—O6—H6 | 109.5 | C29—C30—C38 | 116.8 (5) |
N7—O7—Pr1 | 100.04 (17) | C29—C30—C31 | 125.3 (5) |
N7—O8—Pr1i | 127.27 (19) | C38—C30—C31 | 117.9 (5) |
N7—O8—Pr1 | 95.22 (16) | C32—C31—C30 | 122.0 (4) |
Pr1i—O8—Pr1 | 128.52 (8) | C32—C31—H31 | 119.0 |
C1—N1—C12 | 117.8 (3) | C30—C31—H31 | 119.0 |
C1—N1—Pr1 | 122.5 (2) | C31—C32—C33 | 121.8 (5) |
C12—N1—Pr1 | 119.0 (2) | C31—C32—H32 | 119.1 |
C10—N2—C11 | 117.5 (3) | C33—C32—H32 | 119.1 |
C10—N2—Pr1 | 120.8 (2) | C34—C33—C32 | 123.5 (4) |
C11—N2—Pr1 | 120.47 (19) | C34—C33—C37 | 117.6 (4) |
C27—N3—C38 | 117.2 (4) | C32—C33—C37 | 118.9 (5) |
C36—N4—C37 | 118.4 (4) | C35—C34—C33 | 120.1 (4) |
C39—N5—C50 | 117.6 (5) | C35—C34—H34 | 119.9 |
C48—N6—C49 | 118.2 (4) | C33—C34—H34 | 119.9 |
O9—N7—O7 | 121.7 (3) | C34—C35—C36 | 117.8 (5) |
O9—N7—O8 | 122.3 (3) | C34—C35—H35 | 121.1 |
O7—N7—O8 | 115.9 (3) | C36—C35—H35 | 121.1 |
N1—C1—C2 | 123.5 (3) | N4—C36—C35 | 124.5 (6) |
N1—C1—H1 | 118.2 | N4—C36—H36 | 117.7 |
C2—C1—H1 | 118.2 | C35—C36—H36 | 117.7 |
C3—C2—C1 | 119.2 (4) | N4—C37—C33 | 121.4 (4) |
C3—C2—H2 | 120.4 | N4—C37—C38 | 118.3 (3) |
C1—C2—H2 | 120.4 | C33—C37—C38 | 120.3 (4) |
C2—C3—C4 | 119.6 (3) | N3—C38—C30 | 123.3 (4) |
C2—C3—H3A | 120.2 | N3—C38—C37 | 117.6 (4) |
C4—C3—H3A | 120.2 | C30—C38—C37 | 119.1 (4) |
C3—C4—C12 | 118.0 (3) | N5—C39—C40 | 123.9 (6) |
C3—C4—C5 | 122.3 (3) | N5—C39—H39 | 118.0 |
C12—C4—C5 | 119.7 (3) | C40—C39—H39 | 118.0 |
C6—C5—C4 | 121.1 (3) | C41—C40—C39 | 118.2 (6) |
C6—C5—H5 | 119.4 | C41—C40—H40 | 120.9 |
C4—C5—H5 | 119.4 | C39—C40—H40 | 120.9 |
C5—C6—C7 | 120.9 (3) | C40—C41—C42 | 120.6 (6) |
C5—C6—H6A | 119.6 | C40—C41—H41 | 119.7 |
C7—C6—H6A | 119.6 | C42—C41—H41 | 119.7 |
C8—C7—C11 | 117.6 (3) | C41—C42—C50 | 116.6 (6) |
C8—C7—C6 | 122.2 (3) | C41—C42—C43 | 123.7 (6) |
C11—C7—C6 | 120.2 (3) | C50—C42—C43 | 119.7 (6) |
C9—C8—C7 | 119.8 (3) | C44—C43—C42 | 121.7 (5) |
C9—C8—H8 | 120.1 | C44—C43—H43 | 119.1 |
C7—C8—H8 | 120.1 | C42—C43—H43 | 119.1 |
C8—C9—C10 | 118.7 (4) | C43—C44—C45 | 121.0 (6) |
C8—C9—H9 | 120.6 | C43—C44—H44 | 119.5 |
C10—C9—H9 | 120.6 | C45—C44—H44 | 119.5 |
N2—C10—C9 | 123.8 (3) | C46—C45—C49 | 118.4 (5) |
N2—C10—H10 | 118.1 | C46—C45—C44 | 122.9 (6) |
C9—C10—H10 | 118.1 | C49—C45—C44 | 118.7 (6) |
N2—C11—C7 | 122.5 (3) | C47—C46—C45 | 119.9 (5) |
N2—C11—C12 | 118.8 (3) | C47—C46—H46 | 120.1 |
C7—C11—C12 | 118.7 (3) | C45—C46—H46 | 120.1 |
N1—C12—C4 | 121.8 (3) | C46—C47—C48 | 117.7 (6) |
N1—C12—C11 | 118.8 (3) | C46—C47—H47 | 121.1 |
C4—C12—C11 | 119.4 (3) | C48—C47—H47 | 121.1 |
O1—C13—O2 | 125.3 (3) | N6—C48—C47 | 124.7 (6) |
O1—C13—C14 | 117.5 (3) | N6—C48—H48 | 117.6 |
O2—C13—C14 | 117.2 (3) | C47—C48—H48 | 117.6 |
C19—C14—C15 | 118.5 (3) | N6—C49—C45 | 121.1 (5) |
C19—C14—C13 | 120.4 (3) | N6—C49—C50 | 118.3 (4) |
C15—C14—C13 | 121.0 (3) | C45—C49—C50 | 120.6 (4) |
C14—C15—C16 | 120.8 (3) | N5—C50—C42 | 123.0 (5) |
C14—C15—H15 | 119.6 | N5—C50—C49 | 118.7 (4) |
C16—C15—H15 | 119.6 | C42—C50—C49 | 118.2 (4) |
C17—C16—C15 | 119.8 (3) | ||
O2i—Pr1—O1—C13 | −87.7 (4) | C3—C4—C12—N1 | 1.9 (5) |
O5ii—Pr1—O1—C13 | 64.3 (4) | C5—C4—C12—N1 | −178.3 (3) |
O4—Pr1—O1—C13 | −3.9 (5) | C3—C4—C12—C11 | −177.0 (3) |
O7—Pr1—O1—C13 | −162.2 (4) | C5—C4—C12—C11 | 2.8 (5) |
O8ii—Pr1—O1—C13 | −6.5 (4) | N2—C11—C12—N1 | −2.4 (4) |
O8—Pr1—O1—C13 | −129.9 (4) | C7—C11—C12—N1 | 178.8 (3) |
N2—Pr1—O1—C13 | 132.3 (4) | N2—C11—C12—C4 | 176.5 (3) |
N1—Pr1—O1—C13 | 133.2 (4) | C7—C11—C12—C4 | −2.2 (5) |
O2i—Pr1—O4—C20 | −42.3 (3) | Pr1—O1—C13—O2 | −22.6 (6) |
O5ii—Pr1—O4—C20 | 170.6 (3) | Pr1—O1—C13—C14 | 157.1 (3) |
O1—Pr1—O4—C20 | −118.4 (3) | Pr1ii—O2—C13—O1 | 6.1 (7) |
O7—Pr1—O4—C20 | 36.5 (4) | Pr1ii—O2—C13—C14 | −173.6 (4) |
O8ii—Pr1—O4—C20 | −115.7 (3) | O1—C13—C14—C19 | 170.8 (3) |
O8—Pr1—O4—C20 | 22.2 (3) | O2—C13—C14—C19 | −9.4 (5) |
N2—Pr1—O4—C20 | 93.2 (3) | O1—C13—C14—C15 | −8.8 (5) |
N1—Pr1—O4—C20 | 119.8 (3) | O2—C13—C14—C15 | 171.0 (3) |
O2i—Pr1—O7—N7 | 78.52 (19) | C19—C14—C15—C16 | 0.9 (5) |
O5ii—Pr1—O7—N7 | −117.83 (18) | C13—C14—C15—C16 | −179.5 (3) |
O1—Pr1—O7—N7 | 151.84 (19) | C14—C15—C16—C17 | −1.3 (6) |
O4—Pr1—O7—N7 | −14.1 (2) | C15—C16—C17—O3 | −179.9 (4) |
O8ii—Pr1—O7—N7 | 94.6 (2) | C15—C16—C17—C18 | 0.3 (7) |
O8—Pr1—O7—N7 | 4.48 (16) | O3—C17—C18—C19 | −178.7 (4) |
N2—Pr1—O7—N7 | −73.06 (19) | C16—C17—C18—C19 | 1.1 (7) |
N1—Pr1—O7—N7 | −138.2 (2) | C17—C18—C19—C14 | −1.6 (7) |
O2i—Pr1—O8—N7 | −94.08 (18) | C15—C14—C19—C18 | 0.5 (6) |
O5ii—Pr1—O8—N7 | 108.21 (19) | C13—C14—C19—C18 | −179.1 (4) |
O1—Pr1—O8—N7 | −50.1 (2) | Pr1i—O5—C20—O4 | −57.3 (5) |
O4—Pr1—O8—N7 | 158.81 (18) | Pr1i—O5—C20—C21 | 121.8 (3) |
O7—Pr1—O8—N7 | −4.39 (16) | Pr1—O4—C20—O5 | 20.8 (5) |
O8ii—Pr1—O8—N7 | −148.99 (13) | Pr1—O4—C20—C21 | −158.3 (2) |
N2—Pr1—O8—N7 | 78.51 (17) | O5—C20—C21—C26 | 5.2 (4) |
N1—Pr1—O8—N7 | 31.05 (18) | O4—C20—C21—C26 | −175.7 (3) |
O2i—Pr1—O8—Pr1i | 54.12 (11) | O5—C20—C21—C22 | −171.6 (3) |
O5ii—Pr1—O8—Pr1i | −103.59 (13) | O4—C20—C21—C22 | 7.5 (4) |
O1—Pr1—O8—Pr1i | 98.11 (13) | C26—C21—C22—C23 | 0.6 (6) |
O4—Pr1—O8—Pr1i | −52.99 (11) | C20—C21—C22—C23 | 177.4 (4) |
O7—Pr1—O8—Pr1i | 143.81 (16) | C21—C22—C23—C24 | 0.1 (7) |
O8ii—Pr1—O8—Pr1i | −0.8 (2) | C22—C23—C24—O6 | 178.8 (4) |
N2—Pr1—O8—Pr1i | −133.28 (13) | C22—C23—C24—C25 | 0.1 (6) |
N1—Pr1—O8—Pr1i | 179.25 (10) | O6—C24—C25—C26 | −179.6 (4) |
O2i—Pr1—N1—C1 | −49.4 (3) | C23—C24—C25—C26 | −1.0 (6) |
O5ii—Pr1—N1—C1 | 98.8 (3) | C22—C21—C26—C25 | −1.5 (5) |
O1—Pr1—N1—C1 | 3.9 (3) | C20—C21—C26—C25 | −178.3 (3) |
O4—Pr1—N1—C1 | 153.2 (2) | C24—C25—C26—C21 | 1.7 (5) |
O7—Pr1—N1—C1 | −96.9 (3) | C38—N3—C27—C28 | −1.0 (7) |
O8ii—Pr1—N1—C1 | 55.1 (3) | N3—C27—C28—C29 | −0.6 (9) |
O8—Pr1—N1—C1 | −125.0 (3) | C27—C28—C29—C30 | 1.7 (9) |
N2—Pr1—N1—C1 | −176.9 (3) | C28—C29—C30—C38 | −1.2 (7) |
O2i—Pr1—N1—C12 | 139.7 (2) | C28—C29—C30—C31 | 179.2 (5) |
O5ii—Pr1—N1—C12 | −72.0 (2) | C29—C30—C31—C32 | −178.0 (5) |
O1—Pr1—N1—C12 | −166.9 (2) | C38—C30—C31—C32 | 2.3 (6) |
O4—Pr1—N1—C12 | −17.6 (3) | C30—C31—C32—C33 | 0.1 (7) |
O7—Pr1—N1—C12 | 92.3 (2) | C31—C32—C33—C34 | 176.6 (4) |
O8ii—Pr1—N1—C12 | −115.8 (2) | C31—C32—C33—C37 | −2.5 (6) |
O8—Pr1—N1—C12 | 64.2 (2) | C32—C33—C34—C35 | −178.6 (5) |
N2—Pr1—N1—C12 | 12.3 (2) | C37—C33—C34—C35 | 0.5 (7) |
O2i—Pr1—N2—C10 | 63.6 (3) | C33—C34—C35—C36 | −2.9 (9) |
O5ii—Pr1—N2—C10 | −106.5 (3) | C37—N4—C36—C35 | 0.3 (9) |
O1—Pr1—N2—C10 | −179.9 (2) | C34—C35—C36—N4 | 2.7 (11) |
O4—Pr1—N2—C10 | −24.2 (3) | C36—N4—C37—C33 | −2.9 (6) |
O7—Pr1—N2—C10 | 105.4 (3) | C36—N4—C37—C38 | 176.4 (4) |
O8ii—Pr1—N2—C10 | −66.2 (3) | C34—C33—C37—N4 | 2.6 (6) |
O8—Pr1—N2—C10 | 53.6 (3) | C32—C33—C37—N4 | −178.3 (4) |
N1—Pr1—N2—C10 | 179.1 (3) | C34—C33—C37—C38 | −176.7 (3) |
O2i—Pr1—N2—C11 | −129.3 (2) | C32—C33—C37—C38 | 2.4 (5) |
O5ii—Pr1—N2—C11 | 60.6 (2) | C27—N3—C38—C30 | 1.5 (6) |
O1—Pr1—N2—C11 | −12.8 (3) | C27—N3—C38—C37 | −177.0 (4) |
O4—Pr1—N2—C11 | 142.9 (2) | C29—C30—C38—N3 | −0.5 (6) |
O7—Pr1—N2—C11 | −87.5 (2) | C31—C30—C38—N3 | 179.2 (3) |
O8ii—Pr1—N2—C11 | 100.9 (2) | C29—C30—C38—C37 | 178.0 (4) |
O8—Pr1—N2—C11 | −139.3 (2) | C31—C30—C38—C37 | −2.3 (5) |
N1—Pr1—N2—C11 | −13.8 (2) | N4—C37—C38—N3 | −0.7 (5) |
Pr1—O7—N7—O9 | 170.5 (3) | C33—C37—C38—N3 | 178.6 (3) |
Pr1—O7—N7—O8 | −7.8 (3) | N4—C37—C38—C30 | −179.3 (3) |
Pr1i—O8—N7—O9 | 40.3 (4) | C33—C37—C38—C30 | 0.0 (5) |
Pr1—O8—N7—O9 | −170.9 (3) | C50—N5—C39—C40 | −0.5 (9) |
Pr1i—O8—N7—O7 | −141.3 (2) | N5—C39—C40—C41 | 1.9 (11) |
Pr1—O8—N7—O7 | 7.5 (3) | C39—C40—C41—C42 | −1.2 (10) |
C12—N1—C1—C2 | −0.6 (5) | C40—C41—C42—C50 | −0.7 (8) |
Pr1—N1—C1—C2 | −171.5 (3) | C40—C41—C42—C43 | 179.0 (6) |
N1—C1—C2—C3 | 1.3 (6) | C41—C42—C43—C44 | −179.7 (5) |
C1—C2—C3—C4 | −0.4 (6) | C50—C42—C43—C44 | −0.1 (7) |
C2—C3—C4—C12 | −1.1 (6) | C42—C43—C44—C45 | −2.3 (8) |
C2—C3—C4—C5 | 179.1 (4) | C43—C44—C45—C46 | −176.7 (5) |
C3—C4—C5—C6 | 178.3 (4) | C43—C44—C45—C49 | 1.8 (7) |
C12—C4—C5—C6 | −1.5 (6) | C49—C45—C46—C47 | −1.8 (6) |
C4—C5—C6—C7 | −0.4 (6) | C44—C45—C46—C47 | 176.7 (4) |
C5—C6—C7—C8 | −178.6 (4) | C45—C46—C47—C48 | 2.2 (7) |
C5—C6—C7—C11 | 1.0 (6) | C49—N6—C48—C47 | −0.7 (7) |
C11—C7—C8—C9 | −1.9 (6) | C46—C47—C48—N6 | −1.0 (7) |
C6—C7—C8—C9 | 177.7 (4) | C48—N6—C49—C45 | 1.1 (6) |
C7—C8—C9—C10 | 0.3 (6) | C48—N6—C49—C50 | −178.4 (4) |
C11—N2—C10—C9 | −3.0 (5) | C46—C45—C49—N6 | 0.1 (6) |
Pr1—N2—C10—C9 | 164.5 (3) | C44—C45—C49—N6 | −178.5 (4) |
C8—C9—C10—N2 | 2.3 (6) | C46—C45—C49—C50 | 179.6 (4) |
C10—N2—C11—C7 | 1.2 (5) | C44—C45—C49—C50 | 1.0 (6) |
Pr1—N2—C11—C7 | −166.4 (2) | C39—N5—C50—C42 | −1.6 (7) |
C10—N2—C11—C12 | −177.6 (3) | C39—N5—C50—C49 | 178.1 (4) |
Pr1—N2—C11—C12 | 14.9 (4) | C41—C42—C50—N5 | 2.2 (6) |
C8—C7—C11—N2 | 1.2 (5) | C43—C42—C50—N5 | −177.4 (4) |
C6—C7—C11—N2 | −178.4 (3) | C41—C42—C50—C49 | −177.5 (4) |
C8—C7—C11—C12 | 179.9 (3) | C43—C42—C50—C49 | 2.8 (6) |
C6—C7—C11—C12 | 0.4 (5) | N6—C49—C50—N5 | −3.5 (5) |
C1—N1—C12—C4 | −1.1 (5) | C45—C49—C50—N5 | 177.0 (3) |
Pr1—N1—C12—C4 | 170.2 (2) | N6—C49—C50—C42 | 176.3 (3) |
C1—N1—C12—C11 | 177.9 (3) | C45—C49—C50—C42 | −3.3 (5) |
Pr1—N1—C12—C11 | −10.9 (4) |
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, −y+3/2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6···N4iii | 0.82 | 2.07 | 2.851 (4) | 158 |
O3—H3···N6iv | 0.82 | 2.04 | 2.782 (5) | 150 |
Symmetry codes: (iii) x+1, −y+3/2, z−1/2; (iv) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Pr(C7H5O3)2(NO3)(C12H8N2)]·2C12H8N2 |
Mr | 1017.75 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 291 |
a, b, c (Å) | 21.5625 (2), 23.4621 (2), 8.6030 (1) |
β (°) | 98.899 (1) |
V (Å3) | 4299.88 (7) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 9.27 |
Crystal size (mm) | 0.40 × 0.33 × 0.30 |
Data collection | |
Diffractometer | Oxford Diffraction Gemini S Ultra diffractometer |
Absorption correction | Multi-scan (CrysAlis PRO; Oxford Diffraction, 2006) |
Tmin, Tmax | 0.119, 0.167 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13264, 7308, 6794 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.588 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.092, 1.06 |
No. of reflections | 7308 |
No. of parameters | 606 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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).
D—H···A | D—H | H···A | D···A | 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+3/2, z−1/2; (ii) −x+1, −y+1, −z+1. |
Acknowledgements
The authors thank Dr H. P. Xiao for help with the experiments.
References
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