Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270107043430/bg3052sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270107043430/bg3052Isup2.hkl |
CCDC reference: 669148
For related literature, see: Allen et al. (1987); Chen et al. (2003); Cheng et al. (2000); Deisenhofer & Michel (1989); Luo et al. (2004); Nie et al. (2001); Spek (2003); Xu et al. (1996).
Strontium nitrate (1 mmol), 2,5-dihydroxybenzoic acid (1 mmol), phen (1 mmol) and sodium carbonate (0.5 mmol) were dissolved in a water–ethanol mixture (15 ml, 2:1). The solution was refluxed for 2 h. After cooling to room temperature the solution was filtered. Single crystals of (I) were obtained from the filtrate after 5 d.
H atoms of hydroxy groups and water molecules were located in a difference Fourier map and refined as riding in their as-found relative positions [Uiso(H) = 1.5Ueq(O)]. Other H atoms were placed in calculated positions with C—H distances of 0.93 Å and refined in riding mode with Uiso(H) values of 1.2Ueq(C). The deepest hole is 0.001 Å from the Sr atom.
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
[Sr(C7H5O4)2(C12H8N2)2(H2O)2]·2C12H8N2·4H2O | F(000) = 2528 |
Mr = 1222.75 | Dx = 1.407 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71075 Å |
Hall symbol: -C 2yc | Cell parameters from 18462 reflections |
a = 24.7846 (16) Å | θ = 3.0–24.0° |
b = 13.2694 (8) Å | µ = 1.01 mm−1 |
c = 18.9986 (13) Å | T = 294 K |
β = 112.526 (12)° | Prism, colorless |
V = 5771.5 (8) Å3 | 0.40 × 0.24 × 0.20 mm |
Z = 4 |
Rigaku R-AXIS RAPID IP diffractometer | 5189 independent reflections |
Radiation source: fine-focus sealed tube | 3468 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
Detector resolution: 10.00 pixels mm-1 | θmax = 25.2°, θmin = 3.0° |
ω scan | h = −29→25 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −15→15 |
Tmin = 0.645, Tmax = 0.810 | l = −22→22 |
22817 measured reflections |
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)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.137 | w = 1/[σ2(Fo2) + (0.0426P)2 + 11.6357P] where P = (Fo2 + 2Fc2)/3 |
S = 1.17 | (Δ/σ)max < 0.001 |
5189 reflections | Δρmax = 0.92 e Å−3 |
385 parameters | Δρmin = −1.19 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00085 (15) |
[Sr(C7H5O4)2(C12H8N2)2(H2O)2]·2C12H8N2·4H2O | V = 5771.5 (8) Å3 |
Mr = 1222.75 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 24.7846 (16) Å | µ = 1.01 mm−1 |
b = 13.2694 (8) Å | T = 294 K |
c = 18.9986 (13) Å | 0.40 × 0.24 × 0.20 mm |
β = 112.526 (12)° |
Rigaku R-AXIS RAPID IP diffractometer | 5189 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 3468 reflections with I > 2σ(I) |
Tmin = 0.645, Tmax = 0.810 | Rint = 0.055 |
22817 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.17 | w = 1/[σ2(Fo2) + (0.0426P)2 + 11.6357P] where P = (Fo2 + 2Fc2)/3 |
5189 reflections | Δρmax = 0.92 e Å−3 |
385 parameters | Δρmin = −1.19 e Å−3 |
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 | ||
Sr | 0.5000 | 0.41849 (4) | 0.2500 | 0.0449 (2) | |
N1 | 0.56827 (15) | 0.3801 (2) | 0.39893 (17) | 0.0507 (8) | |
N2 | 0.51319 (14) | 0.5621 (2) | 0.35672 (17) | 0.0500 (8) | |
N3 | 0.63569 (19) | 0.7480 (3) | 0.3427 (2) | 0.0763 (12) | |
N4 | 0.68957 (18) | 0.5723 (3) | 0.4104 (2) | 0.0674 (10) | |
O1 | 0.60384 (12) | 0.4798 (2) | 0.27055 (14) | 0.0550 (7) | |
H1A | 0.6323 | 0.5307 | 0.2932 | 0.082* | |
H1B | 0.6270 | 0.4261 | 0.2729 | 0.082* | |
O2 | 0.63889 (14) | 0.2814 (2) | 0.27761 (19) | 0.0698 (9) | |
O3 | 0.54417 (13) | 0.2647 (2) | 0.21015 (18) | 0.0646 (8) | |
O4 | 0.50660 (14) | 0.1190 (2) | 0.1129 (2) | 0.0823 (10) | |
H4A | 0.5029 | 0.1643 | 0.1455 | 0.123* | |
O5 | 0.73242 (14) | −0.0264 (2) | 0.23051 (19) | 0.0740 (9) | |
H5A | 0.7386 | −0.0863 | 0.2248 | 0.111* | |
O1W | 0.75535 (13) | 0.2948 (2) | 0.31590 (18) | 0.0690 (9) | |
H1C | 0.7621 | 0.2548 | 0.2812 | 0.104* | |
H1D | 0.7233 | 0.2743 | 0.3220 | 0.104* | |
O2W | 0.69718 (14) | 0.6591 (2) | 0.25191 (16) | 0.0718 (9) | |
H2C | 0.6708 | 0.6809 | 0.2700 | 0.108* | |
H2D | 0.7146 | 0.6095 | 0.2836 | 0.108* | |
C1 | 0.5962 (2) | 0.2933 (3) | 0.4205 (3) | 0.0623 (12) | |
H1 | 0.5937 | 0.2463 | 0.3830 | 0.075* | |
C2 | 0.6293 (2) | 0.2683 (4) | 0.4965 (3) | 0.0733 (14) | |
H2 | 0.6488 | 0.2069 | 0.5086 | 0.088* | |
C3 | 0.6326 (2) | 0.3347 (4) | 0.5520 (3) | 0.0718 (14) | |
H3 | 0.6538 | 0.3187 | 0.6028 | 0.086* | |
C4 | 0.60408 (18) | 0.4275 (4) | 0.5328 (2) | 0.0581 (11) | |
C5 | 0.6049 (2) | 0.5005 (5) | 0.5879 (2) | 0.0730 (14) | |
H5 | 0.6253 | 0.4865 | 0.6393 | 0.088* | |
C6 | 0.5771 (2) | 0.5884 (4) | 0.5679 (2) | 0.0710 (14) | |
H6 | 0.5781 | 0.6339 | 0.6056 | 0.085* | |
C7 | 0.54596 (18) | 0.6141 (3) | 0.4896 (2) | 0.0558 (11) | |
C8 | 0.5168 (2) | 0.7050 (4) | 0.4660 (3) | 0.0683 (13) | |
H8 | 0.5179 | 0.7534 | 0.5019 | 0.082* | |
C9 | 0.4868 (2) | 0.7234 (3) | 0.3913 (3) | 0.0700 (13) | |
H9 | 0.4673 | 0.7842 | 0.3754 | 0.084* | |
C10 | 0.4856 (2) | 0.6497 (3) | 0.3381 (2) | 0.0602 (11) | |
H10 | 0.4642 | 0.6628 | 0.2869 | 0.072* | |
C11 | 0.54318 (17) | 0.5439 (3) | 0.4323 (2) | 0.0468 (9) | |
C12 | 0.57235 (17) | 0.4480 (3) | 0.4542 (2) | 0.0484 (10) | |
C13 | 0.7189 (2) | 0.4919 (4) | 0.4443 (3) | 0.0805 (15) | |
H13 | 0.7227 | 0.4400 | 0.4136 | 0.097* | |
C14 | 0.7448 (2) | 0.4790 (5) | 0.5231 (3) | 0.0872 (16) | |
H14 | 0.7657 | 0.4209 | 0.5442 | 0.105* | |
C15 | 0.7385 (2) | 0.5539 (5) | 0.5678 (3) | 0.0851 (17) | |
H15 | 0.7548 | 0.5469 | 0.6205 | 0.102* | |
C16 | 0.7077 (2) | 0.6413 (4) | 0.5354 (3) | 0.0688 (13) | |
C17 | 0.6984 (3) | 0.7226 (5) | 0.5791 (3) | 0.0871 (18) | |
H17 | 0.7139 | 0.7182 | 0.6320 | 0.105* | |
C18 | 0.6679 (3) | 0.8043 (5) | 0.5459 (3) | 0.0900 (18) | |
H18 | 0.6617 | 0.8548 | 0.5759 | 0.108* | |
C19 | 0.6446 (2) | 0.8155 (4) | 0.4651 (3) | 0.0728 (14) | |
C20 | 0.6136 (3) | 0.9011 (4) | 0.4286 (4) | 0.0950 (18) | |
H20 | 0.6060 | 0.9522 | 0.4570 | 0.114* | |
C21 | 0.5949 (3) | 0.9097 (5) | 0.3528 (5) | 0.103 (2) | |
H21 | 0.5740 | 0.9660 | 0.3278 | 0.124* | |
C22 | 0.6076 (3) | 0.8322 (5) | 0.3124 (4) | 0.0989 (19) | |
H22 | 0.5955 | 0.8400 | 0.2599 | 0.119* | |
C23 | 0.6537 (2) | 0.7383 (4) | 0.4194 (3) | 0.0634 (12) | |
C24 | 0.68428 (19) | 0.6482 (4) | 0.4552 (2) | 0.0582 (11) | |
C31 | 0.60667 (18) | 0.1340 (3) | 0.2024 (2) | 0.0479 (9) | |
C32 | 0.56224 (19) | 0.0835 (3) | 0.1438 (3) | 0.0577 (11) | |
C33 | 0.5756 (2) | −0.0048 (3) | 0.1138 (3) | 0.0661 (13) | |
H33 | 0.5464 | −0.0381 | 0.0742 | 0.079* | |
C34 | 0.6315 (2) | −0.0431 (3) | 0.1423 (2) | 0.0615 (12) | |
H34 | 0.6398 | −0.1023 | 0.1221 | 0.074* | |
C35 | 0.67565 (19) | 0.0059 (3) | 0.2007 (2) | 0.0542 (11) | |
C36 | 0.66225 (19) | 0.0927 (3) | 0.2301 (2) | 0.0504 (10) | |
H36 | 0.6916 | 0.1248 | 0.2701 | 0.061* | |
C37 | 0.5963 (2) | 0.2334 (3) | 0.2326 (3) | 0.0544 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sr | 0.0495 (3) | 0.0436 (3) | 0.0396 (3) | 0.000 | 0.0149 (2) | 0.000 |
N1 | 0.056 (2) | 0.0519 (19) | 0.0446 (18) | 0.0012 (16) | 0.0199 (16) | 0.0030 (16) |
N2 | 0.055 (2) | 0.053 (2) | 0.0413 (18) | 0.0026 (16) | 0.0179 (15) | 0.0047 (15) |
N3 | 0.090 (3) | 0.076 (3) | 0.063 (3) | −0.011 (2) | 0.028 (2) | −0.007 (2) |
N4 | 0.075 (3) | 0.072 (3) | 0.058 (2) | −0.008 (2) | 0.029 (2) | −0.015 (2) |
O1 | 0.0518 (17) | 0.0541 (16) | 0.0576 (16) | −0.0085 (13) | 0.0194 (13) | −0.0052 (13) |
O2 | 0.068 (2) | 0.0576 (18) | 0.086 (2) | −0.0002 (16) | 0.0316 (18) | −0.0229 (17) |
O3 | 0.060 (2) | 0.0531 (17) | 0.089 (2) | 0.0059 (15) | 0.0372 (17) | −0.0082 (16) |
O4 | 0.061 (2) | 0.064 (2) | 0.108 (3) | 0.0052 (16) | 0.0163 (19) | −0.0114 (19) |
O5 | 0.065 (2) | 0.0510 (17) | 0.100 (2) | 0.0147 (15) | 0.0255 (18) | −0.0103 (17) |
O1W | 0.068 (2) | 0.0476 (17) | 0.092 (2) | −0.0074 (15) | 0.0309 (17) | −0.0046 (16) |
O2W | 0.081 (2) | 0.078 (2) | 0.0605 (18) | −0.0080 (18) | 0.0326 (16) | 0.0017 (16) |
C1 | 0.066 (3) | 0.063 (3) | 0.060 (3) | 0.005 (2) | 0.028 (2) | 0.010 (2) |
C2 | 0.067 (3) | 0.086 (3) | 0.063 (3) | 0.019 (3) | 0.021 (2) | 0.034 (3) |
C3 | 0.060 (3) | 0.102 (4) | 0.047 (3) | 0.004 (3) | 0.013 (2) | 0.025 (3) |
C4 | 0.050 (2) | 0.088 (3) | 0.034 (2) | −0.009 (2) | 0.0128 (18) | 0.005 (2) |
C5 | 0.059 (3) | 0.122 (5) | 0.036 (2) | −0.015 (3) | 0.016 (2) | −0.002 (3) |
C6 | 0.065 (3) | 0.101 (4) | 0.047 (3) | −0.021 (3) | 0.023 (2) | −0.021 (3) |
C7 | 0.051 (2) | 0.073 (3) | 0.049 (2) | −0.014 (2) | 0.026 (2) | −0.015 (2) |
C8 | 0.070 (3) | 0.075 (3) | 0.068 (3) | −0.012 (3) | 0.036 (3) | −0.024 (3) |
C9 | 0.083 (4) | 0.052 (3) | 0.082 (3) | 0.005 (2) | 0.039 (3) | −0.015 (2) |
C10 | 0.067 (3) | 0.060 (3) | 0.055 (2) | 0.007 (2) | 0.025 (2) | 0.006 (2) |
C11 | 0.043 (2) | 0.059 (2) | 0.041 (2) | −0.0093 (19) | 0.0192 (17) | −0.0052 (19) |
C12 | 0.043 (2) | 0.066 (3) | 0.040 (2) | −0.0066 (19) | 0.0198 (17) | 0.0043 (19) |
C13 | 0.078 (4) | 0.085 (4) | 0.082 (4) | −0.004 (3) | 0.034 (3) | −0.012 (3) |
C14 | 0.071 (4) | 0.097 (4) | 0.085 (4) | −0.003 (3) | 0.021 (3) | 0.007 (3) |
C15 | 0.072 (4) | 0.121 (5) | 0.055 (3) | −0.026 (3) | 0.016 (3) | 0.001 (3) |
C16 | 0.063 (3) | 0.094 (4) | 0.051 (3) | −0.029 (3) | 0.023 (2) | −0.013 (3) |
C17 | 0.097 (4) | 0.121 (5) | 0.052 (3) | −0.044 (4) | 0.039 (3) | −0.038 (3) |
C18 | 0.104 (5) | 0.097 (4) | 0.087 (4) | −0.040 (4) | 0.056 (4) | −0.043 (4) |
C19 | 0.077 (3) | 0.075 (3) | 0.079 (3) | −0.030 (3) | 0.044 (3) | −0.026 (3) |
C20 | 0.102 (5) | 0.071 (4) | 0.128 (6) | −0.022 (3) | 0.062 (4) | −0.025 (4) |
C21 | 0.113 (5) | 0.067 (4) | 0.129 (6) | −0.009 (3) | 0.046 (4) | −0.001 (4) |
C22 | 0.111 (5) | 0.094 (4) | 0.084 (4) | −0.016 (4) | 0.029 (4) | 0.000 (4) |
C23 | 0.065 (3) | 0.073 (3) | 0.059 (3) | −0.026 (2) | 0.031 (2) | −0.022 (2) |
C24 | 0.059 (3) | 0.070 (3) | 0.050 (2) | −0.019 (2) | 0.026 (2) | −0.013 (2) |
C31 | 0.053 (2) | 0.039 (2) | 0.057 (2) | 0.0001 (18) | 0.026 (2) | −0.0008 (18) |
C32 | 0.061 (3) | 0.043 (2) | 0.070 (3) | 0.003 (2) | 0.026 (2) | 0.008 (2) |
C33 | 0.077 (3) | 0.041 (2) | 0.069 (3) | −0.003 (2) | 0.016 (2) | −0.009 (2) |
C34 | 0.080 (3) | 0.036 (2) | 0.067 (3) | 0.006 (2) | 0.026 (2) | −0.005 (2) |
C35 | 0.067 (3) | 0.038 (2) | 0.061 (3) | 0.005 (2) | 0.028 (2) | 0.000 (2) |
C36 | 0.062 (3) | 0.041 (2) | 0.051 (2) | −0.0018 (19) | 0.024 (2) | −0.0014 (18) |
C37 | 0.061 (3) | 0.048 (2) | 0.064 (3) | 0.004 (2) | 0.036 (2) | 0.003 (2) |
Sr—O1i | 2.582 (3) | C6—H6 | 0.9300 |
Sr—O1 | 2.582 (3) | C7—C8 | 1.389 (6) |
Sr—O3i | 2.563 (3) | C7—C11 | 1.414 (5) |
Sr—O3 | 2.563 (3) | C8—C9 | 1.348 (6) |
Sr—N1i | 2.731 (3) | C8—H8 | 0.9300 |
Sr—N1 | 2.731 (3) | C9—C10 | 1.397 (6) |
Sr—N2 | 2.710 (3) | C9—H9 | 0.9300 |
Sr—N2i | 2.710 (3) | C10—H10 | 0.9300 |
N1—C1 | 1.326 (5) | C11—C12 | 1.444 (6) |
N1—C12 | 1.356 (5) | C13—C14 | 1.395 (7) |
N2—C10 | 1.326 (5) | C13—H13 | 0.9300 |
N2—C11 | 1.362 (5) | C14—C15 | 1.355 (8) |
N3—C22 | 1.326 (7) | C14—H14 | 0.9300 |
N3—C23 | 1.358 (6) | C15—C16 | 1.396 (8) |
N4—C13 | 1.312 (6) | C15—H15 | 0.9300 |
N4—C24 | 1.357 (5) | C16—C24 | 1.409 (6) |
O1—H1A | 0.9525 | C16—C17 | 1.433 (7) |
O1—H1B | 0.9053 | C17—C18 | 1.334 (8) |
O2—C37 | 1.249 (5) | C17—H17 | 0.9300 |
O3—C37 | 1.266 (5) | C18—C19 | 1.425 (7) |
O4—C32 | 1.359 (5) | C18—H18 | 0.9300 |
O4—H4A | 0.8926 | C19—C20 | 1.398 (8) |
O5—C35 | 1.369 (5) | C19—C23 | 1.414 (6) |
O5—H5A | 0.8253 | C20—C21 | 1.338 (8) |
O1W—H1C | 0.9103 | C20—H20 | 0.9300 |
O1W—H1D | 0.8881 | C21—C22 | 1.389 (8) |
O2W—H2C | 0.8938 | C21—H21 | 0.9300 |
O2W—H2D | 0.8852 | C22—H22 | 0.9300 |
C1—C2 | 1.400 (6) | C23—C24 | 1.440 (6) |
C1—H1 | 0.9300 | C31—C36 | 1.386 (5) |
C2—C3 | 1.352 (7) | C31—C32 | 1.400 (6) |
C2—H2 | 0.9300 | C31—C37 | 1.499 (5) |
C3—C4 | 1.397 (6) | C32—C33 | 1.398 (6) |
C3—H3 | 0.9300 | C33—C34 | 1.378 (6) |
C4—C5 | 1.420 (7) | C33—H33 | 0.9300 |
C4—C12 | 1.423 (5) | C34—C35 | 1.386 (6) |
C5—C6 | 1.333 (7) | C34—H34 | 0.9300 |
C5—H5 | 0.9300 | C35—C36 | 1.375 (5) |
C6—C7 | 1.430 (6) | C36—H36 | 0.9300 |
O3i—Sr—O3 | 74.49 (14) | C8—C9—H9 | 120.5 |
O3i—Sr—O1i | 77.39 (9) | C10—C9—H9 | 120.5 |
O3—Sr—O1i | 136.04 (9) | N2—C10—C9 | 123.7 (4) |
O3i—Sr—O1 | 136.04 (9) | N2—C10—H10 | 118.2 |
O3—Sr—O1 | 77.39 (9) | C9—C10—H10 | 118.2 |
O1i—Sr—O1 | 143.27 (12) | N2—C11—C7 | 122.7 (4) |
O3i—Sr—N2 | 106.36 (10) | N2—C11—C12 | 118.1 (3) |
O3—Sr—N2 | 146.95 (10) | C7—C11—C12 | 119.2 (4) |
O1i—Sr—N2 | 73.68 (9) | N1—C12—C4 | 122.2 (4) |
O1—Sr—N2 | 80.66 (9) | N1—C12—C11 | 118.8 (3) |
O3i—Sr—N2i | 146.95 (10) | C4—C12—C11 | 119.0 (4) |
O3—Sr—N2i | 106.36 (10) | N4—C13—C14 | 124.5 (5) |
O1i—Sr—N2i | 80.66 (9) | N4—C13—H13 | 117.7 |
O1—Sr—N2i | 73.68 (9) | C14—C13—H13 | 117.7 |
N2—Sr—N2i | 90.60 (13) | C15—C14—C13 | 117.9 (6) |
O3i—Sr—N1i | 89.57 (10) | C15—C14—H14 | 121.1 |
O3—Sr—N1i | 73.19 (10) | C13—C14—H14 | 121.1 |
O1i—Sr—N1i | 73.51 (9) | C14—C15—C16 | 120.5 (5) |
O1—Sr—N1i | 113.66 (9) | C14—C15—H15 | 119.8 |
N2—Sr—N1i | 139.07 (10) | C16—C15—H15 | 119.8 |
N2i—Sr—N1i | 60.44 (9) | C15—C16—C24 | 117.4 (5) |
O3i—Sr—N1 | 73.19 (10) | C15—C16—C17 | 123.5 (5) |
O3—Sr—N1 | 89.57 (10) | C24—C16—C17 | 119.1 (5) |
O1i—Sr—N1 | 113.66 (9) | C18—C17—C16 | 121.7 (5) |
O1—Sr—N1 | 73.51 (9) | C18—C17—H17 | 119.1 |
N2—Sr—N1 | 60.44 (9) | C16—C17—H17 | 119.1 |
N2i—Sr—N1 | 139.07 (10) | C17—C18—C19 | 121.0 (5) |
N1i—Sr—N1 | 158.52 (14) | C17—C18—H18 | 119.5 |
C1—N1—C12 | 117.6 (3) | C19—C18—H18 | 119.5 |
C1—N1—Sr | 121.6 (3) | C20—C19—C23 | 118.1 (5) |
C12—N1—Sr | 120.7 (2) | C20—C19—C18 | 122.5 (6) |
C10—N2—C11 | 117.0 (3) | C23—C19—C18 | 119.4 (5) |
C10—N2—Sr | 121.0 (3) | C21—C20—C19 | 120.1 (6) |
C11—N2—Sr | 121.6 (2) | C21—C20—H20 | 120.0 |
C22—N3—C23 | 116.6 (5) | C19—C20—H20 | 120.0 |
C13—N4—C24 | 117.6 (4) | C20—C21—C22 | 118.3 (6) |
Sr—O1—H1A | 144.6 | C20—C21—H21 | 120.9 |
Sr—O1—H1B | 109.7 | C22—C21—H21 | 120.9 |
H1A—O1—H1B | 100.9 | N3—C22—C21 | 125.1 (6) |
C37—O3—Sr | 131.2 (3) | N3—C22—H22 | 117.4 |
C32—O4—H4A | 106.9 | C21—C22—H22 | 117.4 |
C35—O5—H5A | 117.5 | N3—C23—C19 | 121.7 (5) |
H1C—O1W—H1D | 109.7 | N3—C23—C24 | 118.9 (4) |
H2C—O2W—H2D | 102.6 | C19—C23—C24 | 119.4 (4) |
N1—C1—C2 | 123.7 (5) | N4—C24—C16 | 122.1 (5) |
N1—C1—H1 | 118.2 | N4—C24—C23 | 118.7 (4) |
C2—C1—H1 | 118.2 | C16—C24—C23 | 119.3 (4) |
C3—C2—C1 | 119.1 (5) | C36—C31—C32 | 118.5 (4) |
C3—C2—H2 | 120.4 | C36—C31—C37 | 119.6 (4) |
C1—C2—H2 | 120.4 | C32—C31—C37 | 121.8 (4) |
C2—C3—C4 | 119.9 (4) | O4—C32—C33 | 118.2 (4) |
C2—C3—H3 | 120.1 | O4—C32—C31 | 122.4 (4) |
C4—C3—H3 | 120.1 | C33—C32—C31 | 119.3 (4) |
C3—C4—C5 | 123.1 (4) | C34—C33—C32 | 120.5 (4) |
C3—C4—C12 | 117.6 (4) | C34—C33—H33 | 119.7 |
C5—C4—C12 | 119.4 (4) | C32—C33—H33 | 119.7 |
C6—C5—C4 | 121.7 (4) | C33—C34—C35 | 120.6 (4) |
C6—C5—H5 | 119.1 | C33—C34—H34 | 119.7 |
C4—C5—H5 | 119.1 | C35—C34—H34 | 119.7 |
C5—C6—C7 | 121.3 (4) | O5—C35—C36 | 117.7 (4) |
C5—C6—H6 | 119.3 | O5—C35—C34 | 123.7 (4) |
C7—C6—H6 | 119.3 | C36—C35—C34 | 118.6 (4) |
C8—C7—C11 | 117.2 (4) | C35—C36—C31 | 122.5 (4) |
C8—C7—C6 | 123.3 (4) | C35—C36—H36 | 118.8 |
C11—C7—C6 | 119.4 (4) | C31—C36—H36 | 118.8 |
C9—C8—C7 | 120.3 (4) | O2—C37—O3 | 123.3 (4) |
C9—C8—H8 | 119.8 | O2—C37—C31 | 119.2 (4) |
C7—C8—H8 | 119.8 | O3—C37—C31 | 117.5 (4) |
C8—C9—C10 | 119.0 (4) | ||
O3i—Sr—N1—C1 | 60.6 (3) | Sr—N1—C12—C4 | 175.4 (3) |
O3—Sr—N1—C1 | −13.3 (3) | C1—N1—C12—C11 | 179.0 (4) |
O1i—Sr—N1—C1 | 128.2 (3) | Sr—N1—C12—C11 | −4.2 (5) |
O1—Sr—N1—C1 | −90.2 (3) | C3—C4—C12—N1 | 1.4 (6) |
N2—Sr—N1—C1 | −178.7 (4) | C5—C4—C12—N1 | −177.8 (4) |
N2i—Sr—N1—C1 | −128.2 (3) | C3—C4—C12—C11 | −178.9 (4) |
N1i—Sr—N1—C1 | 22.7 (3) | C5—C4—C12—C11 | 1.9 (6) |
O3i—Sr—N1—C12 | −116.0 (3) | N2—C11—C12—N1 | −0.6 (5) |
O3—Sr—N1—C12 | 170.1 (3) | C7—C11—C12—N1 | 178.4 (4) |
O1i—Sr—N1—C12 | −48.4 (3) | N2—C11—C12—C4 | 179.8 (3) |
O1—Sr—N1—C12 | 93.1 (3) | C7—C11—C12—C4 | −1.2 (6) |
N2—Sr—N1—C12 | 4.6 (3) | C24—N4—C13—C14 | 0.2 (8) |
N2i—Sr—N1—C12 | 55.2 (3) | N4—C13—C14—C15 | 1.1 (9) |
N1i—Sr—N1—C12 | −153.9 (3) | C13—C14—C15—C16 | −0.9 (8) |
O3i—Sr—N2—C10 | −118.8 (3) | C14—C15—C16—C24 | −0.4 (7) |
O3—Sr—N2—C10 | 154.7 (3) | C14—C15—C16—C17 | 178.7 (5) |
O1i—Sr—N2—C10 | −47.6 (3) | C15—C16—C17—C18 | −178.9 (5) |
O1—Sr—N2—C10 | 105.8 (3) | C24—C16—C17—C18 | 0.2 (8) |
N2i—Sr—N2—C10 | 32.5 (3) | C16—C17—C18—C19 | −1.8 (9) |
N1i—Sr—N2—C10 | −9.7 (4) | C17—C18—C19—C20 | −178.6 (5) |
N1—Sr—N2—C10 | −177.9 (3) | C17—C18—C19—C23 | 0.5 (8) |
O3i—Sr—N2—C11 | 54.2 (3) | C23—C19—C20—C21 | −2.0 (8) |
O3—Sr—N2—C11 | −32.4 (4) | C18—C19—C20—C21 | 177.1 (5) |
O1i—Sr—N2—C11 | 125.3 (3) | C19—C20—C21—C22 | −0.5 (9) |
O1—Sr—N2—C11 | −81.2 (3) | C23—N3—C22—C21 | −0.7 (9) |
N2i—Sr—N2—C11 | −154.6 (3) | C20—C21—C22—N3 | 2.0 (10) |
N1i—Sr—N2—C11 | 163.2 (3) | C22—N3—C23—C19 | −2.0 (7) |
N1—Sr—N2—C11 | −5.0 (3) | C22—N3—C23—C24 | 179.9 (5) |
O3i—Sr—O3—C37 | −115.4 (4) | C20—C19—C23—N3 | 3.4 (7) |
O1i—Sr—O3—C37 | −167.6 (3) | C18—C19—C23—N3 | −175.7 (4) |
O1—Sr—O3—C37 | 30.4 (4) | C20—C19—C23—C24 | −178.6 (4) |
N2—Sr—O3—C37 | −19.2 (5) | C18—C19—C23—C24 | 2.3 (7) |
N2i—Sr—O3—C37 | 99.0 (4) | C13—N4—C24—C16 | −1.7 (7) |
N1i—Sr—O3—C37 | 150.2 (4) | C13—N4—C24—C23 | 178.3 (4) |
N1—Sr—O3—C37 | −42.8 (4) | C15—C16—C24—N4 | 1.8 (7) |
C12—N1—C1—C2 | 0.0 (6) | C17—C16—C24—N4 | −177.3 (4) |
Sr—N1—C1—C2 | −176.7 (3) | C15—C16—C24—C23 | −178.2 (4) |
N1—C1—C2—C3 | 1.3 (7) | C17—C16—C24—C23 | 2.6 (6) |
C1—C2—C3—C4 | −1.2 (7) | N3—C23—C24—N4 | −5.8 (6) |
C2—C3—C4—C5 | 179.1 (5) | C19—C23—C24—N4 | 176.1 (4) |
C2—C3—C4—C12 | −0.1 (7) | N3—C23—C24—C16 | 174.3 (4) |
C3—C4—C5—C6 | −179.9 (5) | C19—C23—C24—C16 | −3.8 (6) |
C12—C4—C5—C6 | −0.8 (7) | C36—C31—C32—O4 | −179.6 (4) |
C4—C5—C6—C7 | −1.0 (7) | C37—C31—C32—O4 | −2.8 (6) |
C5—C6—C7—C8 | −179.6 (5) | C36—C31—C32—C33 | −1.9 (6) |
C5—C6—C7—C11 | 1.7 (7) | C37—C31—C32—C33 | 174.9 (4) |
C11—C7—C8—C9 | 0.6 (7) | O4—C32—C33—C34 | 179.0 (4) |
C6—C7—C8—C9 | −178.2 (4) | C31—C32—C33—C34 | 1.2 (7) |
C7—C8—C9—C10 | 0.1 (7) | C32—C33—C34—C35 | −0.6 (7) |
C11—N2—C10—C9 | 1.4 (6) | C33—C34—C35—O5 | −178.4 (4) |
Sr—N2—C10—C9 | 174.6 (4) | C33—C34—C35—C36 | 0.7 (7) |
C8—C9—C10—N2 | −1.2 (7) | O5—C35—C36—C31 | 177.7 (4) |
C10—N2—C11—C7 | −0.6 (6) | C34—C35—C36—C31 | −1.5 (6) |
Sr—N2—C11—C7 | −173.8 (3) | C32—C31—C36—C35 | 2.1 (6) |
C10—N2—C11—C12 | 178.4 (4) | C37—C31—C36—C35 | −174.8 (4) |
Sr—N2—C11—C12 | 5.2 (5) | Sr—O3—C37—O2 | −6.3 (6) |
C8—C7—C11—N2 | −0.4 (6) | Sr—O3—C37—C31 | 174.3 (2) |
C6—C7—C11—N2 | 178.4 (4) | C36—C31—C37—O2 | 6.0 (6) |
C8—C7—C11—C12 | −179.3 (4) | C32—C31—C37—O2 | −170.8 (4) |
C6—C7—C11—C12 | −0.5 (6) | C36—C31—C37—O3 | −174.6 (4) |
C1—N1—C12—C4 | −1.4 (6) | C32—C31—C37—O3 | 8.6 (6) |
Symmetry code: (i) −x+1, y, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···N4 | 0.95 | 2.20 | 2.959 (5) | 136 |
O1—H1B···O2 | 0.91 | 1.94 | 2.759 (4) | 150 |
O4—H4A···O3 | 0.89 | 1.83 | 2.589 (4) | 141 |
O5—H5A···O1Wii | 0.82 | 1.79 | 2.589 (4) | 163 |
O1W—H1C···O2Wii | 0.91 | 1.87 | 2.729 (4) | 155 |
O1W—H1D···O2 | 0.89 | 1.94 | 2.699 (5) | 143 |
O2W—H2C···N3 | 0.90 | 2.09 | 2.950 (6) | 160 |
O2W—H2D···O5iii | 0.88 | 2.31 | 2.961 (4) | 131 |
Symmetry codes: (ii) −x+3/2, y−1/2, −z+1/2; (iii) −x+3/2, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Sr(C7H5O4)2(C12H8N2)2(H2O)2]·2C12H8N2·4H2O |
Mr | 1222.75 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 294 |
a, b, c (Å) | 24.7846 (16), 13.2694 (8), 18.9986 (13) |
β (°) | 112.526 (12) |
V (Å3) | 5771.5 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.01 |
Crystal size (mm) | 0.40 × 0.24 × 0.20 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID IP diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.645, 0.810 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 22817, 5189, 3468 |
Rint | 0.055 |
(sin θ/λ)max (Å−1) | 0.599 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.137, 1.17 |
No. of reflections | 5189 |
No. of parameters | 385 |
H-atom treatment | H-atom parameters constrained |
w = 1/[σ2(Fo2) + (0.0426P)2 + 11.6357P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 0.92, −1.19 |
Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···N4 | 0.95 | 2.20 | 2.959 (5) | 136 |
O1—H1B···O2 | 0.91 | 1.94 | 2.759 (4) | 150 |
O4—H4A···O3 | 0.89 | 1.83 | 2.589 (4) | 141 |
O5—H5A···O1Wi | 0.82 | 1.79 | 2.589 (4) | 163 |
O1W—H1C···O2Wi | 0.91 | 1.87 | 2.729 (4) | 155 |
O1W—H1D···O2 | 0.89 | 1.94 | 2.699 (5) | 143 |
O2W—H2C···N3 | 0.90 | 2.09 | 2.950 (6) | 160 |
O2W—H2D···O5ii | 0.88 | 2.31 | 2.961 (4) | 131 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) −x+3/2, y+1/2, −z+1/2. |
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As π–π stacking between aromatic rings plays an important role in electron transfer process in some biological system (Deisenhofer & Michel, 1989), the nature of π–π stacking has attracted our attention in past years. In a structure with a typical π–π stacking, the face-to-face separation between parallel aromatic rings is much shorter than the van der Waals thickness of the aromatic ring. In order to understand the nature of π–π stacking we have made efforts to investigate the effective factors which prompt the shorter contact of adjacent aromatic rings. A series of metal complexes incorporating aromatic ligands such as phenanthroline (Nie et al., 2001), benzimidazole (Chen et al., 2003), bipyridine (Xu et al., 1996), diaminobithiazole (Luo et al., 2004) and substituted benzoate (Cheng et al., 2000) has been prepared in our laboratory, and their crystal structures have been determined. As a part of our ongoing investigations on the nature of π–π stacking, the title compound, (I), including both coordinated and uncoordinated phenanthroline (phen), has been prepared. We present here its crystal structure in order to show the effect of metal coordination on π–π stacking between phen rings.
The crystal structure of (I) consists of an SrII complex, an uncoordinated phen molecule and solvent water molecules. The SrII ion is located on a crystallographic twofold axis. Two phen ligands chelate a single SrII ion, while two dihydroxybenzoate (dhba) anions and two water molecules complete the distorted SrN4O4 tetragonal antiprismatic coordination geometry (Fig. 1). The Sr—N and Sr—O bond distances (Table 1) are comparable to those found in related structures (Cambridge Structural Database; updated November 2007; Allen, 2002).
A partially overlapped arrangement of parallel phen rings is observed between coordinated and between uncoordinated phen rings (Fig. 2); this fact allowed us to study the effect of metal coordination on aromatic stacking. The face-to-face separation between parallel, uncoordinated N3-phen and N3ii-phen rings is 3.550 (14) Å [symmetry code: (ii) −x + 3/2, −y + 3/2, −z + 1], which is close to the van der Waals thickness of an aromatic ring and reveals a rather weak π–π stacking, whereas the face-to-face separation between the parallel, coordinated N1-phen and N1iii-phen rings [symmetry code: (iii) −x + 1, −y + 1, −z + 1] is 3.436 (13) Å, suggesting a stronger π–π stacking interaction.
Furthermore, the coordinated N1-phen ring is nearly parallel to the uncoordinated N3-phen ring with a small dihedral angle of 7.03 (7)°. These two phen rings also partially overlap one another (Fig. 3). A PLATON calculation (Spek, 2003) shows the two different perpendicular distances from the centre-of-gravity of one benzene ring to the other benzene ring plane to be 3.519 and 3.489 Å (s.u. values available?). The mean value of 3.504 (15) Å is taken to represent the average face-to-face separation between nearly parallel uncoordinated and coordinated phen rings. It is perceivably shorter than 3.550 (14) Å between uncoordinated phen rings but longer than 3.436 (13) Å between coordinated phen rings.
A similar phenomenon was also observed in the crystal structure of an MnII complex with the benzimidazole (bzim) ligand, which was determined by our group previously (Chen et al., 2003). The face-to-face separation between parallel, uncoordinated bzim rings is 3.60 (6) Å but the separation between parallel, coordinated bzim rings is 3.40 (4) Å.
These findings show the difference in face-to-face separations between coordinated aromatic rings and between uncoordinated aromatic rings, and suggest the effect of metal coordination on π–π stacking between aromatic rings, i.e. coordination to a metal cation may result in a shorter face-to-face separation and a stronger π–π stacking between aromatic rings.
Extensive hydrogen bonding occurs in the crystal structure (Table 2).