Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807050969/hk2343sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807050969/hk2343Isup2.hkl |
CCDC reference: 1168219
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.011 Å
- R factor = 0.043
- wR factor = 0.117
- Data-to-parameter ratio = 17.1
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for N9
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.13 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.74 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.79 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C6 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C23 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C33 PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C15 -C20 1.36 Ang. PLAT335_ALERT_2_C Large Benzene C-C Range ....... C4 -C6 0.19 Ang. PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 11 PLAT414_ALERT_2_C Short Intra D-H..H-X H1 .. H7A .. 1.91 Ang. PLAT420_ALERT_2_C D-H Without Acceptor N3 - H3A ... ? PLAT420_ALERT_2_C D-H Without Acceptor N6 - H6A ... ? PLAT420_ALERT_2_C D-H Without Acceptor N9 - H9A ... ? PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 72.00 A 3
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Ce1 (9) 4.79 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 6
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 18 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 13 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
Crystals of the title compound were synthesized using hydrothermal method in a 23 ml Teflon-lined Parr bomb. Cerium (III) nitrate hexahydrate (434.1 mg, 1 mmol), phen (198 mg, 1 mmol), anilinoacetamide (290.4 mg, 2 mmol) and distilled water (12 g) were placed into the bomb and sealed. The bomb was then heated under autogenous pressure up to 453 K over the course of 7 d and allowed to cool at room temperature for 24 h. Upon opening the bomb, a clear colorless solution was decanted from small colorless crystals. These crystals were washed with distilled water followed by ethanol, and allowed to air-dry at room temperature.
H1A and H6A (for NH) were located in difference syntheses and refined isotropically [N—H = 0.80 (2) and 0.84 (5) Å, Uiso(H) = 0.073 (19) and 0.09 (2) Å2]. The remaining H atoms were positioned geometrically, with N—H = 0.86 Å (for NH) and C—H = 0.93 and 0.97 Å, for aromatic and methylene H atoms and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C,N).
The crystal structures of catena-Poly[hexakis(µ2-anilinoacetamide-O,N)bis- (1,10-phenanthroline-N,N')disamarium(III)], (II), and catena-Poly[hexakis- (µ2-anilinoacetamide-O,N)bis(1,10-phenanthroline-N,N')dipraseodymium(III)], (III), have previously been reported (Liu & Zhu, 2007a,b). The crystal structure determination of the title compound, (I), has been carried out in order to elucidate the molecular conformation and to compare it with those of (II) and (III). We report herein the crystal structure of (I).
In the molecule of (I) (Fig. 1), the ligand bond lengths and angles (Table 1) are within normal ranges (Allen et al., 1987). It has an inversion centre midway between the two CeIII ions, which are bridged by two tridentate, two bidentate and four monodentate (within the binuclear unit) acetamide groups. Each Ce atom is nine-coordinated by two N atoms of 1,10-phenanthroline (phen) ligand and four O and three N atoms of anilinoacetamide ligands. The Ce—O and Ce—N bonds are in the range of [2.526 (3)–2.565 (3) Å] and [2.415 (3)–2.828 (4) Å], respectively (Table 1), as in (II) and (III).
In the crystal structure, intermolecular C—H···O, C—H···N, N—H···N and N—H···O hydrogen bonds (Table 2, Fig. 2) result in the formation of a supramolecular network structure; an intramolecular N—H···O hydrogen bond (Table 2) is also present, as in (II) and (III).
The three compounds, (I), (II) and (III), are isostructural.
For related structures, see: Liu & Zhu (2007a,b). For bond-length data, see: Allen et al. (1987).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL (Siemens, 1996).
[Ce2(C8H8N2O)6(C12H8N2)2] | F(000) = 1556 |
Mr = 1535.68 | Dx = 1.506 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 8802 reflections |
a = 20.1131 (12) Å | θ = 2.4–26.6° |
b = 8.5037 (11) Å | µ = 1.39 mm−1 |
c = 20.6993 (15) Å | T = 273 K |
β = 107.011 (2)° | Plate, colorless |
V = 3385.4 (5) Å3 | 0.33 × 0.13 × 0.07 mm |
Z = 2 |
Bruker SMART CCD area-detector diffractometer | 7024 independent reflections |
Radiation source: fine-focus sealed tube | 4796 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
φ and ω scans | θmax = 26.7°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −25→24 |
Tmin = 0.653, Tmax = 0.904 | k = −10→10 |
25721 measured reflections | l = −26→26 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.117 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0642P)2] where P = (Fo2 + 2Fc2)/3 |
7024 reflections | (Δ/σ)max = 0.002 |
411 parameters | Δρmax = 1.36 e Å−3 |
6 restraints | Δρmin = −0.64 e Å−3 |
[Ce2(C8H8N2O)6(C12H8N2)2] | V = 3385.4 (5) Å3 |
Mr = 1535.68 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 20.1131 (12) Å | µ = 1.39 mm−1 |
b = 8.5037 (11) Å | T = 273 K |
c = 20.6993 (15) Å | 0.33 × 0.13 × 0.07 mm |
β = 107.011 (2)° |
Bruker SMART CCD area-detector diffractometer | 7024 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4796 reflections with I > 2σ(I) |
Tmin = 0.653, Tmax = 0.904 | Rint = 0.042 |
25721 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 6 restraints |
wR(F2) = 0.117 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 1.36 e Å−3 |
7024 reflections | Δρmin = −0.64 e Å−3 |
411 parameters |
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 | ||
Ce1 | 0.931202 (12) | 0.19065 (3) | 0.964279 (11) | 0.03965 (10) | |
O1 | 0.84610 (15) | −0.0357 (4) | 0.91874 (15) | 0.0497 (7) | |
O2 | 1.06674 (17) | −0.0827 (4) | 0.92144 (15) | 0.0542 (8) | |
O3 | 1.00727 (19) | 0.6128 (4) | 1.09090 (15) | 0.0618 (9) | |
N1 | 0.94022 (18) | 0.4223 (4) | 1.03386 (16) | 0.0355 (7) | |
H1A | 0.925 (3) | 0.336 (3) | 1.035 (3) | 0.073 (19)* | |
N2 | 0.94701 (16) | −0.1394 (4) | 0.97694 (15) | 0.0373 (8) | |
H2A | 0.9440 | −0.0471 | 0.9928 | 0.045* | |
N3 | 0.97072 (17) | 0.0611 (4) | 0.87531 (15) | 0.0350 (7) | |
H3A | 0.9398 | 0.0552 | 0.8366 | 0.042* | |
N4 | 0.7968 (2) | 0.2339 (5) | 0.9667 (2) | 0.0515 (9) | |
N5 | 0.8345 (2) | 0.3062 (4) | 0.85476 (19) | 0.0520 (10) | |
N6 | 0.9878 (2) | 0.5261 (5) | 1.20638 (17) | 0.0490 (10) | |
H6A | 0.962 (3) | 0.604 (4) | 1.2059 (19) | 0.09 (2)* | |
N7 | 1.11808 (19) | −0.0158 (5) | 0.82168 (18) | 0.0541 (10) | |
H7A | 1.1397 | −0.0730 | 0.8556 | 0.065* | |
N9 | 0.78536 (19) | −0.3271 (4) | 0.8986 (2) | 0.0504 (10) | |
H9A | 0.7626 | −0.3418 | 0.8569 | 0.060* | |
C1 | 0.7788 (3) | 0.1913 (6) | 1.0203 (3) | 0.0682 (15) | |
H1 | 0.8136 | 0.1682 | 1.0599 | 0.082* | |
C2 | 0.7093 (3) | 0.1792 (8) | 1.0200 (4) | 0.089 (2) | |
H2 | 0.6982 | 0.1509 | 1.0590 | 0.107* | |
C3 | 0.6579 (3) | 0.2098 (9) | 0.9611 (4) | 0.094 (2) | |
H3 | 0.6115 | 0.1976 | 0.9594 | 0.113* | |
C4 | 0.6746 (3) | 0.2577 (9) | 0.9055 (4) | 0.0814 (18) | |
C5 | 0.7462 (3) | 0.2665 (6) | 0.9092 (3) | 0.0567 (13) | |
C6 | 0.6222 (4) | 0.2944 (10) | 0.8394 (5) | 0.115 (3) | |
H6 | 0.5751 | 0.2828 | 0.8350 | 0.138* | |
C7 | 0.6417 (4) | 0.3426 (10) | 0.7877 (4) | 0.107 (3) | |
H7 | 0.6080 | 0.3704 | 0.7480 | 0.128* | |
C8 | 0.7136 (3) | 0.3534 (7) | 0.7909 (3) | 0.0742 (17) | |
C9 | 0.7659 (3) | 0.3093 (5) | 0.8506 (3) | 0.0573 (13) | |
C10 | 0.7356 (4) | 0.4047 (8) | 0.7375 (3) | 0.093 (2) | |
H10 | 0.7032 | 0.4408 | 0.6984 | 0.112* | |
C11 | 0.8044 (4) | 0.4030 (8) | 0.7413 (3) | 0.088 (2) | |
H11 | 0.8192 | 0.4366 | 0.7050 | 0.105* | |
C12 | 0.8525 (3) | 0.3499 (6) | 0.8009 (3) | 0.0687 (15) | |
H12 | 0.8992 | 0.3451 | 0.8026 | 0.082* | |
C13 | 1.0285 (3) | 0.0024 (5) | 0.8772 (2) | 0.0483 (11) | |
C14 | 1.0524 (3) | 0.0514 (6) | 0.8173 (2) | 0.0587 (12) | |
H14A | 1.0186 | 0.0174 | 0.7758 | 0.070* | |
H14B | 1.0556 | 0.1651 | 0.8162 | 0.070* | |
C15 | 1.1459 (3) | 0.0139 (7) | 0.7695 (3) | 0.0664 (14) | |
C16 | 1.2075 (3) | −0.0554 (8) | 0.7761 (3) | 0.0832 (18) | |
H16 | 1.2281 | −0.1165 | 0.8139 | 0.100* | |
C17 | 1.2400 (4) | −0.0360 (9) | 0.7268 (4) | 0.098 (2) | |
H17 | 1.2828 | −0.0829 | 0.7313 | 0.118* | |
C18 | 1.2088 (5) | 0.0529 (9) | 0.6711 (5) | 0.113 (3) | |
H18 | 1.2303 | 0.0642 | 0.6373 | 0.136* | |
C19 | 1.1478 (5) | 0.1241 (10) | 0.6646 (4) | 0.113 (3) | |
H19 | 1.1271 | 0.1848 | 0.6267 | 0.136* | |
C20 | 1.1152 (4) | 0.1057 (8) | 0.7160 (3) | 0.088 (2) | |
H20 | 1.0734 | 0.1561 | 0.7130 | 0.106* | |
C21 | 0.8841 (2) | −0.1526 (6) | 0.9390 (2) | 0.0490 (11) | |
C22 | 0.8580 (3) | −0.3151 (6) | 0.9197 (3) | 0.0603 (13) | |
H22A | 0.8758 | −0.3515 | 0.8836 | 0.072* | |
H22B | 0.8762 | −0.3840 | 0.9582 | 0.072* | |
C23 | 0.7536 (6) | −0.3148 (9) | 0.9457 (7) | 0.1322 (16) | |
C24 | 0.7844 (6) | −0.2804 (9) | 1.0110 (6) | 0.1322 (16) | |
H24 | 0.8321 | −0.2630 | 1.0270 | 0.159* | |
C25 | 0.7417 (5) | −0.2714 (10) | 1.0549 (6) | 0.1322 (16) | |
H25 | 0.7615 | −0.2502 | 1.1006 | 0.159* | |
C26 | 0.6741 (6) | −0.2932 (9) | 1.0306 (6) | 0.1322 (16) | |
H26 | 0.6473 | −0.2810 | 1.0601 | 0.159* | |
C27 | 0.6392 (6) | −0.3342 (10) | 0.9624 (6) | 0.1322 (16) | |
H27 | 0.5918 | −0.3557 | 0.9477 | 0.159* | |
C28 | 0.6799 (5) | −0.3398 (10) | 0.9198 (6) | 0.1322 (16) | |
H28 | 0.6598 | −0.3599 | 0.8741 | 0.159* | |
C29 | 0.9694 (2) | 0.4994 (5) | 1.0863 (2) | 0.0488 (11) | |
C30 | 0.9489 (3) | 0.4458 (6) | 1.1474 (2) | 0.0604 (13) | |
H30A | 0.8997 | 0.4653 | 1.1401 | 0.072* | |
H30B | 0.9568 | 0.3335 | 1.1535 | 0.072* | |
C31 | 0.9744 (3) | 0.4884 (6) | 1.2657 (2) | 0.0597 (13) | |
C32 | 0.9277 (3) | 0.3792 (8) | 1.2718 (3) | 0.0761 (17) | |
H32 | 0.9014 | 0.3243 | 1.2342 | 0.091* | |
C33 | 0.9198 (4) | 0.3506 (11) | 1.3348 (4) | 0.111 (3) | |
H33 | 0.8894 | 0.2725 | 1.3400 | 0.133* | |
C34 | 0.9565 (4) | 0.4364 (10) | 1.3898 (3) | 0.107 (2) | |
H34 | 0.9484 | 0.4218 | 1.4314 | 0.129* | |
C35 | 1.0041 (4) | 0.5418 (9) | 1.3836 (3) | 0.094 (2) | |
H35 | 1.0303 | 0.5962 | 1.4215 | 0.112* | |
C36 | 1.0145 (3) | 0.5699 (8) | 1.3222 (3) | 0.0767 (16) | |
H36 | 1.0478 | 0.6422 | 1.3182 | 0.092* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ce1 | 0.04649 (16) | 0.03386 (16) | 0.03378 (14) | −0.00159 (11) | 0.00422 (10) | 0.00055 (10) |
O1 | 0.0509 (17) | 0.0379 (18) | 0.0521 (18) | 0.0000 (15) | 0.0024 (14) | −0.0035 (14) |
O2 | 0.068 (2) | 0.050 (2) | 0.0463 (18) | 0.0089 (16) | 0.0186 (15) | 0.0125 (15) |
O3 | 0.090 (3) | 0.054 (2) | 0.0426 (18) | −0.026 (2) | 0.0214 (17) | −0.0037 (15) |
N1 | 0.057 (2) | 0.0186 (17) | 0.0296 (17) | −0.0075 (16) | 0.0104 (14) | −0.0058 (14) |
N2 | 0.0371 (18) | 0.0324 (18) | 0.0354 (18) | −0.0023 (14) | −0.0003 (14) | 0.0033 (14) |
N3 | 0.0417 (18) | 0.0379 (19) | 0.0238 (15) | 0.0063 (16) | 0.0071 (13) | 0.0012 (14) |
N4 | 0.051 (2) | 0.046 (2) | 0.051 (2) | 0.0040 (18) | 0.0046 (18) | −0.0080 (18) |
N5 | 0.064 (3) | 0.043 (2) | 0.040 (2) | 0.0017 (19) | 0.0006 (17) | 0.0005 (17) |
N6 | 0.072 (3) | 0.046 (2) | 0.0306 (19) | −0.022 (2) | 0.0181 (17) | −0.0057 (16) |
N7 | 0.055 (2) | 0.069 (3) | 0.044 (2) | 0.018 (2) | 0.0241 (18) | 0.0224 (19) |
N9 | 0.047 (2) | 0.035 (2) | 0.057 (2) | −0.0140 (17) | −0.0025 (18) | −0.0067 (17) |
C1 | 0.063 (3) | 0.079 (4) | 0.063 (3) | 0.007 (3) | 0.019 (3) | 0.002 (3) |
C2 | 0.062 (4) | 0.120 (6) | 0.092 (5) | 0.008 (4) | 0.032 (4) | −0.012 (4) |
C3 | 0.054 (4) | 0.112 (6) | 0.113 (6) | −0.005 (4) | 0.018 (4) | −0.013 (5) |
C4 | 0.056 (3) | 0.093 (5) | 0.080 (4) | 0.006 (3) | −0.004 (3) | −0.021 (4) |
C5 | 0.055 (3) | 0.042 (3) | 0.064 (3) | 0.006 (2) | 0.003 (2) | −0.009 (2) |
C6 | 0.058 (4) | 0.154 (9) | 0.106 (6) | 0.016 (4) | −0.017 (4) | −0.026 (6) |
C7 | 0.082 (5) | 0.116 (6) | 0.087 (5) | 0.038 (4) | −0.030 (4) | −0.019 (5) |
C8 | 0.079 (4) | 0.067 (4) | 0.053 (3) | 0.018 (3) | −0.018 (3) | −0.011 (3) |
C9 | 0.067 (3) | 0.037 (3) | 0.053 (3) | 0.004 (2) | −0.007 (2) | −0.006 (2) |
C10 | 0.121 (6) | 0.074 (5) | 0.052 (4) | 0.018 (4) | −0.024 (4) | 0.000 (3) |
C11 | 0.129 (6) | 0.080 (5) | 0.038 (3) | −0.004 (4) | 0.000 (3) | 0.012 (3) |
C12 | 0.087 (4) | 0.057 (3) | 0.053 (3) | −0.001 (3) | 0.005 (3) | 0.009 (2) |
C13 | 0.066 (3) | 0.038 (3) | 0.038 (2) | −0.011 (2) | 0.011 (2) | −0.0029 (19) |
C14 | 0.069 (3) | 0.058 (3) | 0.051 (3) | 0.004 (3) | 0.020 (2) | 0.009 (2) |
C15 | 0.073 (4) | 0.073 (4) | 0.061 (3) | −0.008 (3) | 0.032 (3) | 0.001 (3) |
C16 | 0.084 (4) | 0.098 (5) | 0.079 (4) | 0.004 (4) | 0.041 (3) | −0.005 (4) |
C17 | 0.099 (5) | 0.096 (6) | 0.119 (6) | −0.003 (4) | 0.063 (5) | −0.004 (5) |
C18 | 0.155 (7) | 0.088 (5) | 0.139 (7) | −0.015 (5) | 0.109 (6) | −0.003 (5) |
C19 | 0.151 (7) | 0.119 (6) | 0.096 (5) | 0.020 (6) | 0.076 (5) | 0.034 (5) |
C20 | 0.107 (5) | 0.097 (5) | 0.080 (4) | 0.004 (4) | 0.056 (4) | 0.023 (4) |
C21 | 0.052 (3) | 0.054 (3) | 0.036 (2) | −0.003 (2) | 0.0047 (19) | −0.005 (2) |
C22 | 0.069 (3) | 0.047 (3) | 0.059 (3) | 0.004 (3) | 0.009 (3) | −0.005 (2) |
C23 | 0.144 (4) | 0.095 (3) | 0.183 (4) | 0.018 (3) | 0.087 (4) | 0.031 (3) |
C24 | 0.144 (4) | 0.095 (3) | 0.183 (4) | 0.018 (3) | 0.087 (4) | 0.031 (3) |
C25 | 0.144 (4) | 0.095 (3) | 0.183 (4) | 0.018 (3) | 0.087 (4) | 0.031 (3) |
C26 | 0.144 (4) | 0.095 (3) | 0.183 (4) | 0.018 (3) | 0.087 (4) | 0.031 (3) |
C27 | 0.144 (4) | 0.095 (3) | 0.183 (4) | 0.018 (3) | 0.087 (4) | 0.031 (3) |
C28 | 0.144 (4) | 0.095 (3) | 0.183 (4) | 0.018 (3) | 0.087 (4) | 0.031 (3) |
C29 | 0.060 (3) | 0.036 (3) | 0.050 (3) | −0.002 (2) | 0.016 (2) | 0.006 (2) |
C30 | 0.080 (3) | 0.057 (3) | 0.044 (3) | −0.022 (3) | 0.019 (2) | −0.006 (2) |
C31 | 0.080 (3) | 0.058 (3) | 0.040 (3) | −0.003 (3) | 0.016 (2) | 0.004 (2) |
C32 | 0.081 (4) | 0.094 (4) | 0.056 (3) | −0.034 (4) | 0.024 (3) | −0.004 (3) |
C33 | 0.128 (6) | 0.146 (7) | 0.070 (4) | −0.050 (6) | 0.047 (4) | 0.000 (5) |
C34 | 0.130 (6) | 0.145 (7) | 0.055 (4) | −0.032 (6) | 0.040 (4) | 0.008 (4) |
C35 | 0.124 (6) | 0.103 (5) | 0.047 (3) | −0.018 (4) | 0.014 (3) | −0.006 (3) |
C36 | 0.092 (4) | 0.082 (4) | 0.052 (3) | −0.019 (3) | 0.015 (3) | −0.012 (3) |
Ce1—O1 | 2.565 (3) | C8—C9 | 1.418 (7) |
Ce1—O2i | 2.526 (3) | C10—C11 | 1.363 (9) |
Ce1—O3ii | 2.541 (3) | C10—H10 | 0.9300 |
Ce1—N1 | 2.415 (3) | C11—C12 | 1.401 (8) |
Ce1—N2 | 2.828 (4) | C11—H11 | 0.9300 |
Ce1—N2i | 2.435 (3) | C12—H12 | 0.9300 |
Ce1—N3 | 2.469 (3) | C13—C14 | 1.513 (6) |
Ce1—N4 | 2.743 (4) | C14—H14A | 0.9700 |
Ce1—N5 | 2.703 (4) | C14—H14B | 0.9700 |
O1—C21 | 1.249 (5) | C15—C16 | 1.342 (8) |
O2—C13 | 1.242 (5) | C15—C20 | 1.348 (8) |
O2—Ce1i | 2.526 (3) | C16—C17 | 1.373 (9) |
O3—C29 | 1.215 (5) | C16—H16 | 0.9300 |
O3—Ce1ii | 2.541 (3) | C17—C18 | 1.368 (10) |
N1—C29 | 1.257 (6) | C17—H17 | 0.9300 |
N1—H1A | 0.80 (2) | C18—C19 | 1.339 (10) |
N2—C21 | 1.285 (5) | C18—H18 | 0.9300 |
N2—Ce1i | 2.435 (3) | C19—C20 | 1.413 (8) |
N2—H2A | 0.8600 | C19—H19 | 0.9300 |
N3—C13 | 1.254 (5) | C20—H20 | 0.9300 |
N3—H3A | 0.8600 | C21—C22 | 1.490 (7) |
N4—C1 | 1.314 (6) | C22—H22A | 0.9700 |
N4—C5 | 1.349 (6) | C22—H22B | 0.9700 |
N5—C12 | 1.323 (6) | C23—C24 | 1.344 (15) |
N5—C9 | 1.358 (7) | C23—C28 | 1.438 (14) |
N6—C31 | 1.369 (6) | C24—C25 | 1.424 (12) |
N6—C30 | 1.418 (6) | C24—H24 | 0.9300 |
N6—H6A | 0.84 (5) | C25—C26 | 1.317 (13) |
N7—C15 | 1.377 (6) | C25—H25 | 0.9300 |
N7—C14 | 1.419 (6) | C26—C27 | 1.425 (14) |
N7—H7A | 0.8600 | C26—H26 | 0.9300 |
N9—C23 | 1.317 (11) | C27—C28 | 1.367 (11) |
N9—C22 | 1.401 (6) | C27—H27 | 0.9300 |
N9—H9A | 0.8600 | C28—H28 | 0.9300 |
C1—C2 | 1.400 (8) | C29—C30 | 1.510 (6) |
C1—H1 | 0.9300 | C30—H30A | 0.9700 |
C2—C3 | 1.373 (10) | C30—H30B | 0.9700 |
C2—H2 | 0.9300 | C31—C32 | 1.353 (7) |
C3—C4 | 1.353 (9) | C31—C36 | 1.396 (7) |
C3—H3 | 0.9300 | C32—C33 | 1.380 (8) |
C4—C5 | 1.421 (8) | C32—H32 | 0.9300 |
C4—C6 | 1.496 (10) | C33—C34 | 1.372 (10) |
C5—C9 | 1.430 (8) | C33—H33 | 0.9300 |
C6—C7 | 1.308 (11) | C34—C35 | 1.345 (9) |
C6—H6 | 0.9300 | C34—H34 | 0.9300 |
C7—C8 | 1.433 (10) | C35—C36 | 1.368 (8) |
C7—H7 | 0.9300 | C35—H35 | 0.9300 |
C8—C10 | 1.376 (9) | C36—H36 | 0.9300 |
N1—Ce1—N2 | 140.11 (10) | N4—C5—C4 | 121.9 (5) |
N1—Ce1—N3 | 145.53 (11) | N4—C5—C9 | 118.5 (5) |
N1—Ce1—N4 | 77.43 (12) | C4—C5—C9 | 119.6 (5) |
N1—Ce1—N5 | 96.53 (11) | C7—C6—C4 | 120.9 (7) |
N2—Ce1—N3 | 64.79 (10) | C7—C6—H6 | 119.5 |
N2—Ce1—N4 | 102.47 (11) | C4—C6—H6 | 119.5 |
N2—Ce1—N5 | 118.19 (10) | C6—C7—C8 | 121.5 (6) |
N3—Ce1—N4 | 127.42 (11) | C6—C7—H7 | 119.2 |
N3—Ce1—N5 | 81.15 (11) | C8—C7—H7 | 119.2 |
N4—Ce1—N5 | 59.72 (13) | C10—C8—C9 | 117.0 (6) |
O1—Ce1—N1 | 139.17 (11) | C10—C8—C7 | 122.7 (6) |
O1—Ce1—N2 | 48.26 (9) | C9—C8—C7 | 120.3 (6) |
O1—Ce1—N3 | 73.55 (10) | N5—C9—C8 | 122.8 (5) |
O1—Ce1—N4 | 63.38 (11) | N5—C9—C5 | 118.0 (4) |
O1—Ce1—N5 | 74.08 (10) | C8—C9—C5 | 119.2 (5) |
N1—Ce1—N2i | 87.65 (12) | C11—C10—C8 | 120.6 (5) |
N2i—Ce1—N3 | 78.25 (11) | C11—C10—H10 | 119.7 |
N1—Ce1—O2i | 76.13 (11) | C8—C10—H10 | 119.7 |
N2i—Ce1—O2i | 74.24 (10) | C10—C11—C12 | 118.9 (6) |
N3—Ce1—O2i | 128.00 (11) | C10—C11—H11 | 120.6 |
N1—Ce1—O2i | 76.13 (11) | C12—C11—H11 | 120.6 |
N2i—Ce1—O2i | 74.24 (10) | N5—C12—C11 | 123.0 (6) |
N3—Ce1—O2i | 128.00 (11) | N5—C12—H12 | 118.5 |
O2i—Ce1—O2i | 0.0 (2) | C11—C12—H12 | 118.5 |
N1—Ce1—O2i | 76.13 (11) | O2—C13—N3 | 128.5 (4) |
N2i—Ce1—O2i | 74.24 (10) | O2—C13—C14 | 119.2 (4) |
N3—Ce1—O2i | 128.00 (11) | N3—C13—C14 | 112.2 (4) |
O2i—Ce1—O2i | 0.0 (2) | N7—C14—C13 | 110.5 (4) |
O2i—Ce1—O2i | 0.0 (2) | N7—C14—H14A | 109.6 |
N1—Ce1—O3ii | 76.71 (11) | C13—C14—H14A | 109.6 |
N2i—Ce1—O3ii | 77.95 (11) | N7—C14—H14B | 109.6 |
N3—Ce1—O3ii | 69.69 (11) | C13—C14—H14B | 109.6 |
O2i—Ce1—O3ii | 141.55 (11) | H14A—C14—H14B | 108.1 |
O2i—Ce1—O3ii | 141.55 (11) | C16—C15—C20 | 121.7 (5) |
O2i—Ce1—O3ii | 141.55 (11) | C16—C15—N7 | 114.5 (5) |
N2i—Ce1—O1 | 121.00 (11) | C20—C15—N7 | 123.8 (5) |
O2i—Ce1—O1 | 84.14 (10) | C15—C16—C17 | 119.8 (7) |
O2i—Ce1—O1 | 84.14 (10) | C15—C16—H16 | 120.1 |
O2i—Ce1—O1 | 84.14 (10) | C17—C16—H16 | 120.1 |
O3ii—Ce1—O1 | 133.54 (10) | C18—C17—C16 | 119.5 (7) |
N2i—Ce1—N5 | 148.86 (12) | C18—C17—H17 | 120.3 |
O2i—Ce1—N5 | 136.73 (12) | C16—C17—H17 | 120.3 |
O2i—Ce1—N5 | 136.73 (12) | C19—C18—C17 | 121.0 (7) |
O2i—Ce1—N5 | 136.73 (12) | C19—C18—H18 | 119.5 |
O3ii—Ce1—N5 | 73.10 (12) | C17—C18—H18 | 119.5 |
N2i—Ce1—N4 | 150.19 (11) | C18—C19—C20 | 119.2 (7) |
O2i—Ce1—N4 | 77.16 (11) | C18—C19—H19 | 120.4 |
O2i—Ce1—N4 | 77.16 (11) | C20—C19—H19 | 120.4 |
O2i—Ce1—N4 | 77.16 (11) | C15—C20—C19 | 118.8 (7) |
O3ii—Ce1—N4 | 122.16 (12) | C15—C20—H20 | 120.6 |
N2i—Ce1—N2 | 72.94 (12) | C19—C20—H20 | 120.6 |
O2i—Ce1—N2 | 65.30 (10) | O1—C21—N2 | 122.1 (4) |
O2i—Ce1—N2 | 65.30 (10) | O1—C21—C22 | 121.0 (4) |
O2i—Ce1—N2 | 65.30 (10) | N2—C21—C22 | 116.8 (4) |
O3ii—Ce1—N2 | 129.65 (10) | N9—C22—C21 | 113.8 (4) |
N1—Ce1—H1A | 17.2 (9) | N9—C22—H22A | 108.8 |
N2i—Ce1—H1A | 90.7 (17) | C21—C22—H22A | 108.8 |
N3—Ce1—H1A | 161.7 (11) | N9—C22—H22B | 108.8 |
O2i—Ce1—H1A | 60.8 (11) | C21—C22—H22B | 108.8 |
O2i—Ce1—H1A | 60.8 (11) | H22A—C22—H22B | 107.7 |
O2i—Ce1—H1A | 60.8 (11) | N9—C23—C24 | 125.5 (11) |
O3ii—Ce1—H1A | 93.9 (9) | N9—C23—C28 | 112.6 (11) |
O1—Ce1—H1A | 124.8 (11) | C24—C23—C28 | 121.9 (10) |
N5—Ce1—H1A | 102.3 (16) | C23—C24—C25 | 117.9 (11) |
N4—Ce1—H1A | 67.9 (15) | C23—C24—H24 | 121.1 |
N2—Ce1—H1A | 126.1 (12) | C25—C24—H24 | 121.1 |
C21—O1—Ce1 | 101.4 (3) | C26—C25—C24 | 119.8 (12) |
C13—O2—Ce1i | 137.7 (3) | C26—C25—H25 | 120.1 |
C29—O3—Ce1ii | 149.7 (3) | C24—C25—H25 | 120.1 |
C29—N1—Ce1 | 151.1 (3) | C25—C26—C27 | 124.5 (10) |
C29—N1—H1A | 122 (4) | C25—C26—H26 | 117.7 |
Ce1—N1—H1A | 47 (4) | C27—C26—H26 | 117.7 |
C21—N2—Ce1i | 163.2 (3) | C28—C27—C26 | 115.7 (11) |
C21—N2—Ce1 | 88.1 (3) | C28—C27—H27 | 122.2 |
Ce1i—N2—Ce1 | 107.06 (12) | C26—C27—H27 | 122.2 |
C21—N2—H2A | 98.4 | C27—C28—C23 | 120.1 (11) |
Ce1i—N2—H2A | 98.4 | C27—C28—H28 | 119.9 |
C13—N3—Ce1 | 130.7 (3) | C23—C28—H28 | 119.9 |
C13—N3—H3A | 114.6 | O3—C29—N1 | 127.2 (4) |
Ce1—N3—H3A | 114.6 | O3—C29—C30 | 119.5 (4) |
C1—N4—C5 | 118.6 (5) | N1—C29—C30 | 113.1 (4) |
C1—N4—Ce1 | 119.7 (3) | N6—C30—C29 | 111.0 (4) |
C5—N4—Ce1 | 120.3 (3) | N6—C30—H30A | 109.4 |
C12—N5—C9 | 117.7 (4) | C29—C30—H30A | 109.4 |
C12—N5—Ce1 | 120.2 (3) | N6—C30—H30B | 109.4 |
C9—N5—Ce1 | 121.9 (3) | C29—C30—H30B | 109.4 |
C31—N6—C30 | 117.1 (4) | H30A—C30—H30B | 108.0 |
C31—N6—H6A | 84.8 (17) | C32—C31—N6 | 124.7 (5) |
C30—N6—H6A | 101 (4) | C32—C31—C36 | 120.5 (5) |
C15—N7—C14 | 117.4 (4) | N6—C31—C36 | 114.7 (5) |
C15—N7—H7A | 121.3 | C32—C31—H6A | 124 (2) |
C14—N7—H7A | 121.3 | C36—C31—H6A | 106 (2) |
C23—N9—C22 | 116.8 (7) | C31—C32—C33 | 119.1 (6) |
C23—N9—H9A | 121.6 | C31—C32—H32 | 120.5 |
C22—N9—H9A | 121.6 | C33—C32—H32 | 120.5 |
N4—C1—C2 | 122.6 (6) | C34—C33—C32 | 120.5 (7) |
N4—C1—H1 | 118.7 | C34—C33—H33 | 119.8 |
C2—C1—H1 | 118.7 | C32—C33—H33 | 119.8 |
C3—C2—C1 | 118.8 (6) | C35—C34—C33 | 120.0 (6) |
C3—C2—H2 | 120.6 | C35—C34—H34 | 120.0 |
C1—C2—H2 | 120.6 | C33—C34—H34 | 120.0 |
C4—C3—C2 | 120.2 (6) | C34—C35—C36 | 120.8 (6) |
C4—C3—H3 | 119.9 | C34—C35—H35 | 119.6 |
C2—C3—H3 | 119.9 | C36—C35—H35 | 119.6 |
C3—C4—C5 | 118.0 (6) | C35—C36—C31 | 119.0 (6) |
C3—C4—C6 | 123.8 (7) | C35—C36—H36 | 120.5 |
C5—C4—C6 | 118.1 (7) | C31—C36—H36 | 120.5 |
Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+2, −y+1, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O2i | 0.93 | 2.43 | 3.125 (7) | 131 |
C10—H10···O1iii | 0.93 | 2.34 | 3.210 (6) | 155 |
C12—H12···N6ii | 0.93 | 2.58 | 3.425 (7) | 152 |
C12—H12···O3ii | 0.93 | 2.47 | 3.062 (7) | 122 |
C22—H22B···N1iv | 0.97 | 2.38 | 3.319 (6) | 164 |
N1—H1A···O2i | 0.80 (2) | 2.32 (3) | 3.048 (5) | 152 (6) |
N2—H2A···N2i | 0.86 | 2.63 | 3.144 (7) | 120 |
N2—H2A···O2i | 0.86 | 2.15 | 2.900 (5) | 145 |
N7—H7A···O2 | 0.86 | 2.28 | 2.627 (4) | 104 |
Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+2, −y+1, −z+2; (iii) −x+3/2, y+1/2, −z+3/2; (iv) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | [Ce2(C8H8N2O)6(C12H8N2)2] |
Mr | 1535.68 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 273 |
a, b, c (Å) | 20.1131 (12), 8.5037 (11), 20.6993 (15) |
β (°) | 107.011 (2) |
V (Å3) | 3385.4 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.39 |
Crystal size (mm) | 0.33 × 0.13 × 0.07 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.653, 0.904 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 25721, 7024, 4796 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.632 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.117, 1.07 |
No. of reflections | 7024 |
No. of parameters | 411 |
No. of restraints | 6 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 1.36, −0.64 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996).
Ce1—O1 | 2.565 (3) | Ce1—N2i | 2.435 (3) |
Ce1—O2i | 2.526 (3) | Ce1—N3 | 2.469 (3) |
Ce1—O3ii | 2.541 (3) | Ce1—N4 | 2.743 (4) |
Ce1—N1 | 2.415 (3) | Ce1—N5 | 2.703 (4) |
Ce1—N2 | 2.828 (4) | ||
N1—Ce1—N2 | 140.11 (10) | N3—Ce1—N5 | 81.15 (11) |
N1—Ce1—N3 | 145.53 (11) | N4—Ce1—N5 | 59.72 (13) |
N1—Ce1—N4 | 77.43 (12) | O1—Ce1—N1 | 139.17 (11) |
N1—Ce1—N5 | 96.53 (11) | O1—Ce1—N2 | 48.26 (9) |
N2—Ce1—N3 | 64.79 (10) | O1—Ce1—N3 | 73.55 (10) |
N2—Ce1—N4 | 102.47 (11) | O1—Ce1—N4 | 63.38 (11) |
N2—Ce1—N5 | 118.19 (10) | O1—Ce1—N5 | 74.08 (10) |
N3—Ce1—N4 | 127.42 (11) |
Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+2, −y+1, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O2i | 0.93 | 2.43 | 3.125 (7) | 131 |
C10—H10···O1iii | 0.93 | 2.34 | 3.210 (6) | 155 |
C12—H12···N6ii | 0.93 | 2.58 | 3.425 (7) | 152 |
C12—H12···O3ii | 0.93 | 2.47 | 3.062 (7) | 122 |
C22—H22B···N1iv | 0.97 | 2.38 | 3.319 (6) | 164 |
N1—H1A···O2i | 0.80 (2) | 2.32 (3) | 3.048 (5) | 152 (6) |
N2—H2A···N2i | 0.86 | 2.63 | 3.144 (7) | 120 |
N2—H2A···O2i | 0.86 | 2.15 | 2.900 (5) | 145 |
N7—H7A···O2 | 0.86 | 2.28 | 2.627 (4) | 104 |
Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+2, −y+1, −z+2; (iii) −x+3/2, y+1/2, −z+3/2; (iv) x, y−1, z. |
The crystal structures of catena-Poly[hexakis(µ2-anilinoacetamide-O,N)bis- (1,10-phenanthroline-N,N')disamarium(III)], (II), and catena-Poly[hexakis- (µ2-anilinoacetamide-O,N)bis(1,10-phenanthroline-N,N')dipraseodymium(III)], (III), have previously been reported (Liu & Zhu, 2007a,b). The crystal structure determination of the title compound, (I), has been carried out in order to elucidate the molecular conformation and to compare it with those of (II) and (III). We report herein the crystal structure of (I).
In the molecule of (I) (Fig. 1), the ligand bond lengths and angles (Table 1) are within normal ranges (Allen et al., 1987). It has an inversion centre midway between the two CeIII ions, which are bridged by two tridentate, two bidentate and four monodentate (within the binuclear unit) acetamide groups. Each Ce atom is nine-coordinated by two N atoms of 1,10-phenanthroline (phen) ligand and four O and three N atoms of anilinoacetamide ligands. The Ce—O and Ce—N bonds are in the range of [2.526 (3)–2.565 (3) Å] and [2.415 (3)–2.828 (4) Å], respectively (Table 1), as in (II) and (III).
In the crystal structure, intermolecular C—H···O, C—H···N, N—H···N and N—H···O hydrogen bonds (Table 2, Fig. 2) result in the formation of a supramolecular network structure; an intramolecular N—H···O hydrogen bond (Table 2) is also present, as in (II) and (III).
The three compounds, (I), (II) and (III), are isostructural.