Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021101/ng2262sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021101/ng2262Isup2.hkl |
CCDC reference: 650537
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.005 Å
- R factor = 0.038
- wR factor = 0.100
- Data-to-parameter ratio = 15.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 8 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 H2 O
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C8 = ... R PLAT794_ALERT_5_G Check Predicted Bond Valency for Mn1 (2) 2.06
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
For the cobalt(II) and nickel(II) complexes of the title carboxylic acid, see: Deng et al. (2007a,b).
The title complex was prepared by the addition of MnCl2.4H2O (10 mmol) and 1,10-phenanthroline (10 mmol) to a solution of 2-(p-CPOPH2) (15 mmol) in H2O/MeOH (V/V = 1:1) solution. The pH value was adjusted to 5 with NaOH (0.2 M) solution. Colorless crystals were obtained from the filtered solution at room temperature over several days. CH&N analysis. Calc. for C22H24N2O9Mn: C 51.27, H 4.69, N 5.43. Found: C 51.26, H 4.67, N 5.46%.
The H atoms were placed in calculated positions with C—H = 0.93 or 0.97 Å and Uiso(H) = 1.2Ueq (C) and were included in the refinement in the riding model approximation. The H atoms of water molecules and hydroxyl groups were located in difference Fourier maps and refined with the O—H distance restrained to 0.85 (1) Å and Uiso(H) = 1.5Ueq(O).
Our studies have addressed the metal derivatives of carboxyphenoxypropionic acids for the construction of supramolecular architectures. ecently, we have reported the structures of cobalt(II) and nickel(II) derivatives of 2-(4-carboxylatophenoxy)propionic acid (Deng et al., 2007a,b). In the title Mn complex (I) (Fig. 1), the 2-(p-CPOP)2- anion coordinates in a monodentate fashion to the Mn atom through the carboxylate group. The Mn atom is chelated by the phenanthroline and is also linked to three water molecules. A three-dimensional supramolecular network is constructed from π-π stacking between the 1,10-phenanthroline rings (centroid-centroid distance being 3.689 (5) and 3.869 (5) Å) and hydrogen-bonding interactions (Table 2).
For the cobalt(II) and nickel(II) complexes of the title carboxylic acid, see: Deng et al. (2007a,b).
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Fig. 1. Molecular structure of the title compound with 30% probability ellipsoid for the non-H atoms. Dashed lines indicate O—H···O hydrogen bonds. |
[Mn(C10H8O5)(C12H8N2)(H2O)3]·H2O | Z = 2 |
Mr = 515.37 | F(000) = 534 |
Triclinic, P1 | Dx = 1.469 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.5457 (15) Å | Cell parameters from 7678 reflections |
b = 11.073 (2) Å | θ = 3.3–27.5° |
c = 15.372 (3) Å | µ = 0.62 mm−1 |
α = 106.16 (3)° | T = 295 K |
β = 99.53 (3)° | Prism, colourless |
γ = 103.14 (3)° | 0.38 × 0.25 × 0.17 mm |
V = 1164.8 (5) Å3 |
Rigaku R-AXIS RAPID diffractometer | 5280 independent reflections |
Radiation source: fine-focus sealed tube | 3105 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
Detector resolution: 10.000 pixels mm-1 | θmax = 27.5°, θmin = 3.3° |
ω scans | h = −9→9 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −14→14 |
Tmin = 0.826, Tmax = 0.893 | l = −19→19 |
11565 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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0275P)2 + 0.6167P] where P = (Fo2 + 2Fc2)/3 |
5280 reflections | (Δ/σ)max = 0.001 |
332 parameters | Δρmax = 0.56 e Å−3 |
0 restraints | Δρmin = −0.73 e Å−3 |
[Mn(C10H8O5)(C12H8N2)(H2O)3]·H2O | γ = 103.14 (3)° |
Mr = 515.37 | V = 1164.8 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.5457 (15) Å | Mo Kα radiation |
b = 11.073 (2) Å | µ = 0.62 mm−1 |
c = 15.372 (3) Å | T = 295 K |
α = 106.16 (3)° | 0.38 × 0.25 × 0.17 mm |
β = 99.53 (3)° |
Rigaku R-AXIS RAPID diffractometer | 5280 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 3105 reflections with I > 2σ(I) |
Tmin = 0.826, Tmax = 0.893 | Rint = 0.036 |
11565 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.12 | Δρmax = 0.56 e Å−3 |
5280 reflections | Δρmin = −0.73 e Å−3 |
332 parameters |
x | y | z | Uiso*/Ueq | ||
Mn1 | 0.27669 (6) | 0.37228 (4) | 0.71204 (3) | 0.03294 (13) | |
O1W | 0.5797 (3) | 0.4182 (2) | 0.75865 (16) | 0.0471 (5) | |
H1W1 | 0.624 (5) | 0.362 (3) | 0.774 (2) | 0.071* | |
H1W2 | 0.633 (5) | 0.493 (4) | 0.796 (3) | 0.071* | |
O2W | 0.2654 (3) | 0.3051 (2) | 0.83041 (14) | 0.0432 (5) | |
H2W1 | 0.353 (5) | 0.286 (3) | 0.859 (2) | 0.065* | |
H2W2 | 0.170 (5) | 0.286 (3) | 0.857 (2) | 0.065* | |
O3W | −0.0264 (3) | 0.34586 (19) | 0.69778 (14) | 0.0385 (5) | |
H3W1 | −0.086 (4) | 0.309 (3) | 0.734 (2) | 0.058* | |
H3W2 | −0.026 (5) | 0.426 (3) | 0.717 (2) | 0.058* | |
O4W | −0.1908 (3) | 0.6600 (2) | 0.88034 (17) | 0.0560 (6) | |
H4W1 | −0.098 (6) | 0.649 (4) | 0.851 (3) | 0.084* | |
H4W2 | −0.146 (6) | 0.686 (4) | 0.939 (3) | 0.084* | |
O1 | 0.3311 (3) | 0.58037 (17) | 0.75925 (14) | 0.0424 (5) | |
O2 | 0.0499 (3) | 0.60400 (18) | 0.76959 (15) | 0.0479 (5) | |
O3 | 0.5231 (3) | 1.20164 (16) | 0.92263 (13) | 0.0364 (4) | |
O4 | 1.0045 (3) | 1.2598 (2) | 0.92143 (14) | 0.0485 (5) | |
O5 | 0.7683 (3) | 1.25399 (18) | 0.81085 (13) | 0.0425 (5) | |
N1 | 0.2598 (3) | 0.1668 (2) | 0.61862 (15) | 0.0386 (6) | |
N2 | 0.2602 (3) | 0.3778 (2) | 0.56302 (16) | 0.0424 (6) | |
C1 | 0.2238 (4) | 0.6494 (2) | 0.78069 (18) | 0.0343 (6) | |
C2 | 0.3088 (4) | 0.7955 (2) | 0.82068 (18) | 0.0334 (6) | |
C3 | 0.5007 (4) | 0.8509 (2) | 0.84896 (18) | 0.0355 (6) | |
H3 | 0.5789 | 0.7967 | 0.8443 | 0.043* | |
C4 | 0.5795 (4) | 0.9867 (3) | 0.88444 (19) | 0.0366 (6) | |
H4 | 0.7091 | 1.0229 | 0.9028 | 0.044* | |
C5 | 0.4628 (4) | 1.0666 (2) | 0.89205 (17) | 0.0306 (6) | |
C6 | 0.2693 (4) | 1.0124 (3) | 0.8677 (2) | 0.0382 (7) | |
H6 | 0.1911 | 1.0665 | 0.8754 | 0.046* | |
C7 | 0.1938 (4) | 0.8781 (3) | 0.8321 (2) | 0.0382 (7) | |
H7 | 0.0641 | 0.8420 | 0.8153 | 0.046* | |
C8 | 0.7194 (4) | 1.2660 (2) | 0.96311 (18) | 0.0332 (6) | |
H8 | 0.7654 | 1.2279 | 1.0096 | 0.040* | |
C9 | 0.7334 (4) | 1.4088 (3) | 1.0117 (2) | 0.0434 (7) | |
H9A | 0.6928 | 1.4472 | 0.9661 | 0.065* | |
H9B | 0.8612 | 1.4559 | 1.0448 | 0.065* | |
H9C | 0.6549 | 1.4135 | 1.0550 | 0.065* | |
C10 | 0.8382 (4) | 1.2573 (2) | 0.89161 (19) | 0.0332 (6) | |
C11 | 0.2577 (5) | 0.4808 (3) | 0.5357 (2) | 0.0569 (9) | |
H11 | 0.2552 | 0.5577 | 0.5790 | 0.068* | |
C12 | 0.2588 (5) | 0.4788 (4) | 0.4442 (3) | 0.0722 (11) | |
H12 | 0.2587 | 0.5533 | 0.4275 | 0.087* | |
C13 | 0.2601 (5) | 0.3666 (4) | 0.3804 (2) | 0.0705 (11) | |
H13 | 0.2611 | 0.3640 | 0.3195 | 0.085* | |
C14 | 0.2599 (5) | 0.2548 (4) | 0.4058 (2) | 0.0551 (9) | |
C15 | 0.2562 (5) | 0.1317 (5) | 0.3425 (2) | 0.0727 (11) | |
H15 | 0.2568 | 0.1249 | 0.2809 | 0.087* | |
C16 | 0.2517 (6) | 0.0256 (4) | 0.3689 (2) | 0.0722 (11) | |
H16 | 0.2492 | −0.0529 | 0.3256 | 0.087* | |
C17 | 0.2506 (5) | 0.0323 (3) | 0.4632 (2) | 0.0529 (8) | |
C18 | 0.2449 (5) | −0.0746 (3) | 0.4952 (3) | 0.0653 (10) | |
H18 | 0.2390 | −0.1559 | 0.4543 | 0.078* | |
C19 | 0.2480 (5) | −0.0595 (3) | 0.5858 (3) | 0.0641 (10) | |
H19 | 0.2452 | −0.1298 | 0.6079 | 0.077* | |
C20 | 0.2553 (5) | 0.0628 (3) | 0.6457 (2) | 0.0523 (8) | |
H20 | 0.2572 | 0.0720 | 0.7079 | 0.063* | |
C21 | 0.2571 (4) | 0.1526 (3) | 0.52810 (18) | 0.0395 (7) | |
C22 | 0.2592 (4) | 0.2654 (3) | 0.49881 (19) | 0.0407 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Mn1 | 0.0368 (3) | 0.0277 (2) | 0.0340 (2) | 0.00985 (18) | 0.00952 (18) | 0.00888 (18) |
O1W | 0.0373 (13) | 0.0414 (12) | 0.0608 (14) | 0.0123 (10) | 0.0063 (11) | 0.0165 (11) |
O2W | 0.0430 (14) | 0.0543 (13) | 0.0474 (12) | 0.0224 (11) | 0.0180 (10) | 0.0291 (11) |
O3W | 0.0381 (12) | 0.0318 (10) | 0.0457 (12) | 0.0092 (9) | 0.0120 (9) | 0.0123 (10) |
O4W | 0.0417 (15) | 0.0607 (15) | 0.0568 (14) | 0.0119 (12) | 0.0060 (12) | 0.0115 (13) |
O1 | 0.0402 (12) | 0.0265 (10) | 0.0585 (13) | 0.0100 (9) | 0.0148 (10) | 0.0090 (9) |
O2 | 0.0359 (13) | 0.0308 (10) | 0.0685 (14) | 0.0059 (9) | 0.0089 (11) | 0.0086 (10) |
O3 | 0.0350 (11) | 0.0247 (9) | 0.0492 (11) | 0.0085 (8) | 0.0103 (9) | 0.0118 (9) |
O4 | 0.0355 (13) | 0.0656 (14) | 0.0499 (12) | 0.0150 (11) | 0.0133 (10) | 0.0253 (11) |
O5 | 0.0472 (13) | 0.0460 (11) | 0.0385 (11) | 0.0160 (10) | 0.0134 (10) | 0.0166 (10) |
N1 | 0.0442 (15) | 0.0344 (13) | 0.0342 (12) | 0.0113 (11) | 0.0091 (11) | 0.0070 (11) |
N2 | 0.0449 (16) | 0.0479 (15) | 0.0378 (13) | 0.0128 (12) | 0.0085 (11) | 0.0207 (13) |
C1 | 0.0390 (17) | 0.0281 (14) | 0.0371 (15) | 0.0102 (13) | 0.0097 (13) | 0.0123 (12) |
C2 | 0.0384 (17) | 0.0299 (14) | 0.0348 (14) | 0.0086 (12) | 0.0111 (13) | 0.0149 (12) |
C3 | 0.0361 (17) | 0.0294 (14) | 0.0440 (16) | 0.0115 (12) | 0.0142 (13) | 0.0127 (13) |
C4 | 0.0306 (16) | 0.0316 (14) | 0.0488 (16) | 0.0079 (12) | 0.0121 (13) | 0.0145 (13) |
C5 | 0.0367 (16) | 0.0245 (13) | 0.0331 (14) | 0.0088 (12) | 0.0126 (12) | 0.0112 (12) |
C6 | 0.0366 (17) | 0.0301 (14) | 0.0541 (17) | 0.0143 (13) | 0.0159 (14) | 0.0166 (14) |
C7 | 0.0299 (16) | 0.0311 (14) | 0.0542 (18) | 0.0077 (12) | 0.0072 (13) | 0.0180 (14) |
C8 | 0.0320 (16) | 0.0276 (13) | 0.0355 (14) | 0.0048 (12) | 0.0055 (12) | 0.0080 (12) |
C9 | 0.050 (2) | 0.0333 (15) | 0.0421 (16) | 0.0116 (14) | 0.0123 (14) | 0.0056 (13) |
C10 | 0.0365 (17) | 0.0235 (13) | 0.0372 (15) | 0.0057 (12) | 0.0081 (13) | 0.0091 (12) |
C11 | 0.065 (2) | 0.059 (2) | 0.0528 (19) | 0.0197 (18) | 0.0097 (17) | 0.0297 (18) |
C12 | 0.076 (3) | 0.084 (3) | 0.068 (2) | 0.019 (2) | 0.006 (2) | 0.052 (2) |
C13 | 0.062 (3) | 0.107 (3) | 0.044 (2) | 0.015 (2) | 0.0071 (18) | 0.036 (2) |
C14 | 0.046 (2) | 0.082 (2) | 0.0347 (16) | 0.0144 (18) | 0.0073 (15) | 0.0201 (18) |
C15 | 0.065 (3) | 0.108 (3) | 0.0323 (18) | 0.022 (2) | 0.0141 (17) | 0.006 (2) |
C16 | 0.074 (3) | 0.081 (3) | 0.044 (2) | 0.028 (2) | 0.0130 (19) | −0.010 (2) |
C17 | 0.044 (2) | 0.058 (2) | 0.0418 (17) | 0.0126 (16) | 0.0072 (15) | −0.0031 (16) |
C18 | 0.066 (3) | 0.045 (2) | 0.069 (2) | 0.0215 (18) | 0.009 (2) | −0.0064 (19) |
C19 | 0.075 (3) | 0.0363 (18) | 0.075 (2) | 0.0192 (17) | 0.010 (2) | 0.0101 (18) |
C20 | 0.071 (2) | 0.0362 (17) | 0.0478 (18) | 0.0167 (16) | 0.0122 (17) | 0.0106 (15) |
C21 | 0.0330 (17) | 0.0440 (16) | 0.0319 (15) | 0.0068 (13) | 0.0059 (12) | 0.0024 (14) |
C22 | 0.0306 (16) | 0.0554 (19) | 0.0320 (14) | 0.0091 (14) | 0.0082 (12) | 0.0105 (14) |
Mn1—O1 | 2.1318 (19) | C5—C6 | 1.389 (4) |
Mn1—O2W | 2.156 (2) | C6—C7 | 1.376 (4) |
Mn1—O1W | 2.174 (2) | C6—H6 | 0.9300 |
Mn1—O3W | 2.204 (2) | C7—H7 | 0.9300 |
Mn1—N1 | 2.290 (2) | C8—C9 | 1.521 (4) |
Mn1—N2 | 2.292 (2) | C8—C10 | 1.526 (4) |
O1W—H1W1 | 0.84 (4) | C8—H8 | 0.9800 |
O1W—H1W2 | 0.83 (4) | C9—H9A | 0.9600 |
O2W—H2W1 | 0.83 (4) | C9—H9B | 0.9600 |
O2W—H2W2 | 0.90 (4) | C9—H9C | 0.9600 |
O3W—H3W1 | 0.90 (3) | C11—C12 | 1.402 (5) |
O3W—H3W2 | 0.85 (3) | C11—H11 | 0.9300 |
O4W—H4W1 | 0.91 (4) | C12—C13 | 1.354 (5) |
O4W—H4W2 | 0.85 (4) | C12—H12 | 0.9300 |
O1—C1 | 1.256 (3) | C13—C14 | 1.398 (5) |
O2—C1 | 1.257 (3) | C13—H13 | 0.9300 |
O3—C5 | 1.375 (3) | C14—C22 | 1.403 (4) |
O3—C8 | 1.435 (3) | C14—C15 | 1.429 (5) |
O4—C10 | 1.253 (3) | C15—C16 | 1.340 (5) |
O5—C10 | 1.253 (3) | C15—H15 | 0.9300 |
N1—C20 | 1.324 (3) | C16—C17 | 1.432 (5) |
N1—C21 | 1.352 (3) | C16—H16 | 0.9300 |
N2—C11 | 1.322 (4) | C17—C18 | 1.397 (5) |
N2—C22 | 1.354 (4) | C17—C21 | 1.410 (4) |
C1—C2 | 1.501 (4) | C18—C19 | 1.352 (5) |
C2—C3 | 1.379 (4) | C18—H18 | 0.9300 |
C2—C7 | 1.393 (4) | C19—C20 | 1.393 (4) |
C3—C4 | 1.393 (4) | C19—H19 | 0.9300 |
C3—H3 | 0.9300 | C20—H20 | 0.9300 |
C4—C5 | 1.380 (4) | C21—C22 | 1.439 (4) |
C4—H4 | 0.9300 | ||
O1—Mn1—O2W | 108.33 (8) | C2—C7—H7 | 119.5 |
O1—Mn1—O1W | 83.81 (9) | O3—C8—C9 | 105.4 (2) |
O2W—Mn1—O1W | 85.84 (9) | O3—C8—C10 | 113.6 (2) |
O1—Mn1—O3W | 90.70 (8) | C9—C8—C10 | 109.8 (2) |
O2W—Mn1—O3W | 85.06 (9) | O3—C8—H8 | 109.3 |
O1W—Mn1—O3W | 167.32 (8) | C9—C8—H8 | 109.3 |
O1—Mn1—N1 | 159.22 (8) | C10—C8—H8 | 109.3 |
O2W—Mn1—N1 | 91.18 (8) | C8—C9—H9A | 109.5 |
O1W—Mn1—N1 | 90.74 (10) | C8—C9—H9B | 109.5 |
O3W—Mn1—N1 | 98.24 (9) | H9A—C9—H9B | 109.5 |
O1—Mn1—N2 | 88.65 (9) | C8—C9—H9C | 109.5 |
O2W—Mn1—N2 | 162.90 (8) | H9A—C9—H9C | 109.5 |
O1W—Mn1—N2 | 98.30 (9) | H9B—C9—H9C | 109.5 |
O3W—Mn1—N2 | 92.97 (9) | O5—C10—O4 | 125.3 (3) |
N1—Mn1—N2 | 72.27 (9) | O5—C10—C8 | 119.3 (3) |
Mn1—O1W—H1W1 | 118 (2) | O4—C10—C8 | 115.4 (2) |
Mn1—O1W—H1W2 | 115 (3) | N2—C11—C12 | 122.7 (3) |
H1W1—O1W—H1W2 | 111 (4) | N2—C11—H11 | 118.6 |
Mn1—O2W—H2W1 | 124 (2) | C12—C11—H11 | 118.6 |
Mn1—O2W—H2W2 | 130 (2) | C13—C12—C11 | 119.0 (3) |
H2W1—O2W—H2W2 | 105 (3) | C13—C12—H12 | 120.5 |
Mn1—O3W—H3W1 | 120 (2) | C11—C12—H12 | 120.5 |
Mn1—O3W—H3W2 | 100 (2) | C12—C13—C14 | 120.3 (3) |
H3W1—O3W—H3W2 | 105 (3) | C12—C13—H13 | 119.9 |
H4W1—O4W—H4W2 | 110 (4) | C14—C13—H13 | 119.9 |
C1—O1—Mn1 | 130.21 (18) | C13—C14—C22 | 117.0 (3) |
C5—O3—C8 | 118.4 (2) | C13—C14—C15 | 124.0 (3) |
C20—N1—C21 | 117.9 (2) | C22—C14—C15 | 119.0 (3) |
C20—N1—Mn1 | 125.92 (19) | C16—C15—C14 | 122.3 (3) |
C21—N1—Mn1 | 116.17 (18) | C16—C15—H15 | 118.9 |
C11—N2—C22 | 118.1 (3) | C14—C15—H15 | 118.9 |
C11—N2—Mn1 | 126.1 (2) | C15—C16—C17 | 120.5 (3) |
C22—N2—Mn1 | 115.78 (17) | C15—C16—H16 | 119.8 |
O1—C1—O2 | 124.3 (2) | C17—C16—H16 | 119.8 |
O1—C1—C2 | 117.6 (3) | C18—C17—C21 | 117.6 (3) |
O2—C1—C2 | 118.1 (2) | C18—C17—C16 | 123.5 (3) |
C3—C2—C7 | 118.6 (2) | C21—C17—C16 | 119.0 (3) |
C3—C2—C1 | 121.2 (3) | C19—C18—C17 | 119.8 (3) |
C7—C2—C1 | 120.2 (3) | C19—C18—H18 | 120.1 |
C2—C3—C4 | 121.1 (3) | C17—C18—H18 | 120.1 |
C2—C3—H3 | 119.4 | C18—C19—C20 | 119.1 (3) |
C4—C3—H3 | 119.4 | C18—C19—H19 | 120.4 |
C5—C4—C3 | 119.2 (3) | C20—C19—H19 | 120.4 |
C5—C4—H4 | 120.4 | N1—C20—C19 | 123.4 (3) |
C3—C4—H4 | 120.4 | N1—C20—H20 | 118.3 |
O3—C5—C4 | 124.8 (2) | C19—C20—H20 | 118.3 |
O3—C5—C6 | 114.9 (2) | N1—C21—C17 | 122.3 (3) |
C4—C5—C6 | 120.4 (2) | N1—C21—C22 | 117.6 (2) |
C7—C6—C5 | 119.6 (3) | C17—C21—C22 | 120.1 (3) |
C7—C6—H6 | 120.2 | N2—C22—C14 | 122.8 (3) |
C5—C6—H6 | 120.2 | N2—C22—C21 | 118.0 (2) |
C6—C7—C2 | 121.0 (3) | C14—C22—C21 | 119.2 (3) |
C6—C7—H7 | 119.5 | ||
O2W—Mn1—O1—C1 | −76.5 (2) | C5—O3—C8—C9 | −165.6 (2) |
O1W—Mn1—O1—C1 | −160.0 (2) | C5—O3—C8—C10 | 74.1 (3) |
O3W—Mn1—O1—C1 | 8.5 (2) | O3—C8—C10—O5 | 31.7 (3) |
N1—Mn1—O1—C1 | 124.4 (3) | C9—C8—C10—O5 | −86.1 (3) |
N2—Mn1—O1—C1 | 101.5 (2) | O3—C8—C10—O4 | −151.2 (2) |
O1—Mn1—N1—C20 | 157.5 (3) | C9—C8—C10—O4 | 91.0 (3) |
O2W—Mn1—N1—C20 | −2.7 (3) | C22—N2—C11—C12 | −1.6 (5) |
O1W—Mn1—N1—C20 | 83.2 (3) | Mn1—N2—C11—C12 | 176.0 (3) |
O3W—Mn1—N1—C20 | −87.9 (3) | N2—C11—C12—C13 | 0.8 (6) |
N2—Mn1—N1—C20 | −178.4 (3) | C11—C12—C13—C14 | 0.1 (6) |
O1—Mn1—N1—C21 | −21.4 (4) | C12—C13—C14—C22 | −0.3 (5) |
O2W—Mn1—N1—C21 | 178.4 (2) | C12—C13—C14—C15 | 178.3 (4) |
O1W—Mn1—N1—C21 | −95.8 (2) | C13—C14—C15—C16 | −178.4 (4) |
O3W—Mn1—N1—C21 | 93.2 (2) | C22—C14—C15—C16 | 0.1 (6) |
N2—Mn1—N1—C21 | 2.71 (19) | C14—C15—C16—C17 | 0.0 (6) |
O1—Mn1—N2—C11 | −9.4 (3) | C15—C16—C17—C18 | 179.6 (4) |
O2W—Mn1—N2—C11 | 164.1 (3) | C15—C16—C17—C21 | −0.9 (5) |
O1W—Mn1—N2—C11 | −92.9 (3) | C21—C17—C18—C19 | −0.8 (5) |
O3W—Mn1—N2—C11 | 81.3 (3) | C16—C17—C18—C19 | 178.7 (4) |
N1—Mn1—N2—C11 | 179.0 (3) | C17—C18—C19—C20 | 0.5 (6) |
O1—Mn1—N2—C22 | 168.3 (2) | C21—N1—C20—C19 | 0.0 (5) |
O2W—Mn1—N2—C22 | −18.2 (4) | Mn1—N1—C20—C19 | −178.9 (3) |
O1W—Mn1—N2—C22 | 84.8 (2) | C18—C19—C20—N1 | −0.1 (6) |
O3W—Mn1—N2—C22 | −101.0 (2) | C20—N1—C21—C17 | −0.3 (4) |
N1—Mn1—N2—C22 | −3.33 (19) | Mn1—N1—C21—C17 | 178.7 (2) |
Mn1—O1—C1—O2 | −6.8 (4) | C20—N1—C21—C22 | 179.1 (3) |
Mn1—O1—C1—C2 | 174.23 (16) | Mn1—N1—C21—C22 | −1.9 (3) |
O1—C1—C2—C3 | −11.7 (4) | C18—C17—C21—N1 | 0.7 (5) |
O2—C1—C2—C3 | 169.3 (2) | C16—C17—C21—N1 | −178.8 (3) |
O1—C1—C2—C7 | 169.9 (2) | C18—C17—C21—C22 | −178.7 (3) |
O2—C1—C2—C7 | −9.1 (4) | C16—C17—C21—C22 | 1.8 (5) |
C7—C2—C3—C4 | −2.8 (4) | C11—N2—C22—C14 | 1.4 (4) |
C1—C2—C3—C4 | 178.8 (2) | Mn1—N2—C22—C14 | −176.4 (2) |
C2—C3—C4—C5 | 0.6 (4) | C11—N2—C22—C21 | −178.5 (3) |
C8—O3—C5—C4 | −10.1 (4) | Mn1—N2—C22—C21 | 3.7 (3) |
C8—O3—C5—C6 | 170.2 (2) | C13—C14—C22—N2 | −0.5 (5) |
C3—C4—C5—O3 | −177.5 (2) | C15—C14—C22—N2 | −179.1 (3) |
C3—C4—C5—C6 | 2.2 (4) | C13—C14—C22—C21 | 179.4 (3) |
O3—C5—C6—C7 | 177.0 (2) | C15—C14—C22—C21 | 0.8 (5) |
C4—C5—C6—C7 | −2.8 (4) | N1—C21—C22—N2 | −1.2 (4) |
C5—C6—C7—C2 | 0.5 (4) | C17—C21—C22—N2 | 178.2 (3) |
C3—C2—C7—C6 | 2.3 (4) | N1—C21—C22—C14 | 178.9 (3) |
C1—C2—C7—C6 | −179.3 (2) | C17—C21—C22—C14 | −1.7 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O5i | 0.84 (4) | 1.92 (4) | 2.754 (3) | 170 (3) |
O1W—H1W2···O4Wii | 0.83 (4) | 1.96 (4) | 2.774 (4) | 168 (4) |
O2W—H2W1···O3i | 0.83 (4) | 2.03 (4) | 2.847 (3) | 167 (3) |
O2W—H2W2···O4iii | 0.90 (4) | 1.73 (4) | 2.634 (3) | 173 (3) |
O3W—H3W1···O5iii | 0.90 (3) | 1.87 (3) | 2.759 (3) | 170 (3) |
O3W—H3W2···O2 | 0.85 (3) | 1.82 (3) | 2.647 (3) | 163 (3) |
O4W—H4W1···O2 | 0.91 (4) | 1.85 (4) | 2.744 (3) | 168 (4) |
O4W—H4W2···O4iv | 0.85 (4) | 2.08 (4) | 2.925 (3) | 171 (4) |
Symmetry codes: (i) x, y−1, z; (ii) x+1, y, z; (iii) x−1, y−1, z; (iv) −x+1, −y+2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | [Mn(C10H8O5)(C12H8N2)(H2O)3]·H2O |
Mr | 515.37 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 7.5457 (15), 11.073 (2), 15.372 (3) |
α, β, γ (°) | 106.16 (3), 99.53 (3), 103.14 (3) |
V (Å3) | 1164.8 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.62 |
Crystal size (mm) | 0.38 × 0.25 × 0.17 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.826, 0.893 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11565, 5280, 3105 |
Rint | 0.036 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.100, 1.12 |
No. of reflections | 5280 |
No. of parameters | 332 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.56, −0.73 |
Computer programs: RAPID-AUTO (Rigaku, 1998), RAPID-AUTO, CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97.
Mn1—O1 | 2.1318 (19) | Mn1—O3W | 2.204 (2) |
Mn1—O2W | 2.156 (2) | Mn1—N1 | 2.290 (2) |
Mn1—O1W | 2.174 (2) | Mn1—N2 | 2.292 (2) |
O1—Mn1—O2W | 108.33 (8) | O1W—Mn1—N1 | 90.74 (10) |
O1—Mn1—O1W | 83.81 (9) | O3W—Mn1—N1 | 98.24 (9) |
O2W—Mn1—O1W | 85.84 (9) | O1—Mn1—N2 | 88.65 (9) |
O1—Mn1—O3W | 90.70 (8) | O2W—Mn1—N2 | 162.90 (8) |
O2W—Mn1—O3W | 85.06 (9) | O1W—Mn1—N2 | 98.30 (9) |
O1W—Mn1—O3W | 167.32 (8) | O3W—Mn1—N2 | 92.97 (9) |
O1—Mn1—N1 | 159.22 (8) | N1—Mn1—N2 | 72.27 (9) |
O2W—Mn1—N1 | 91.18 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O5i | 0.84 (4) | 1.92 (4) | 2.754 (3) | 170 (3) |
O1W—H1W2···O4Wii | 0.83 (4) | 1.96 (4) | 2.774 (4) | 168 (4) |
O2W—H2W1···O3i | 0.83 (4) | 2.03 (4) | 2.847 (3) | 167 (3) |
O2W—H2W2···O4iii | 0.90 (4) | 1.73 (4) | 2.634 (3) | 173 (3) |
O3W—H3W1···O5iii | 0.90 (3) | 1.87 (3) | 2.759 (3) | 170 (3) |
O3W—H3W2···O2 | 0.85 (3) | 1.82 (3) | 2.647 (3) | 163 (3) |
O4W—H4W1···O2 | 0.91 (4) | 1.85 (4) | 2.744 (3) | 168 (4) |
O4W—H4W2···O4iv | 0.85 (4) | 2.08 (4) | 2.925 (3) | 171 (4) |
Symmetry codes: (i) x, y−1, z; (ii) x+1, y, z; (iii) x−1, y−1, z; (iv) −x+1, −y+2, −z+2. |
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Our studies have addressed the metal derivatives of carboxyphenoxypropionic acids for the construction of supramolecular architectures. ecently, we have reported the structures of cobalt(II) and nickel(II) derivatives of 2-(4-carboxylatophenoxy)propionic acid (Deng et al., 2007a,b). In the title Mn complex (I) (Fig. 1), the 2-(p-CPOP)2- anion coordinates in a monodentate fashion to the Mn atom through the carboxylate group. The Mn atom is chelated by the phenanthroline and is also linked to three water molecules. A three-dimensional supramolecular network is constructed from π-π stacking between the 1,10-phenanthroline rings (centroid-centroid distance being 3.689 (5) and 3.869 (5) Å) and hydrogen-bonding interactions (Table 2).