Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805038559/xu6085sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805038559/xu6085Isup2.hkl |
CCDC reference: 296709
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.007 Å
- Disorder in main residue
- R factor = 0.066
- wR factor = 0.184
- Data-to-parameter ratio = 12.1
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C33 PLAT417_ALERT_2_B Short Inter D-H..H-D H1W1 .. H2W1 .. 2.09 Ang.
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.629 0.911 Tmin(prime) and Tmax expected: 0.833 0.910 RR(prime) = 0.754 Please check that your absorption correction is appropriate. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.75 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.55 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C32 PLAT301_ALERT_3_C Main Residue Disorder ......................... 8.00 Perc. PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT410_ALERT_2_C Short Intra H...H Contact H27 .. H32C .. 1.94 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 10 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 H2 O
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 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 2 ALERT type 4 Improvement, methodology, query or suggestion
Manganese dichloride hexahydrate (0.47 g, 2 mmol), 1,10-phenanthroline (0.80 g, 4 mmol) and 3-carboxyphenoxyacetic acid (0.39 g, 2 mmol) were dissolved in a small volume of hot water. The clear solution was set aside for several days to obtain yellow prismatic block-shaped? crystals of (I). Analysis calculated for C33H32MnN4O10: C 56.64, H 4.61, N 8.01%; found: C 56.67, H 4.59, N 7.99%.
The C-bound H atoms were positioned geometrically (C—H = 0.93 or 0.97 Å) and were included in the refinement in the riding-model approximation, with Uiso(H) = 1.2 times Ueq(C). The H atoms of the water molecules were placed at chemically sensible positions on the basis of hydrogen bonds but they were not refined; their displacement parameters were similarly tied. The water molecules were restrained to behave in an approximately isotropic manner. All H···H contacts exceed 2 Å.
The oxyacetate arm of the dianion is disordered over two positions; the occupancies refined to 0.44 (1) and 0.56 (1). A number of restraints were imposed. The O3—C32 and O3–C-32' distances were restrained to be within 0.01 Å of each other, as were the C32—C33 and C32'—C33' pair. The four C—O distances of the —CO2 portion were also restrained in this manner; owing to this restraint, the electrons in the portion are assumed to be delocalized. The vibrations of the disordered atoms were restrained to behave in a nearly isotropic fashion.
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.
[Mn(C9H6O5)(C12H8N2)2(H2O)]·4H2O | Z = 2 |
Mr = 699.57 | F(000) = 726 |
Triclinic, P1 | Dx = 1.437 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.123 (2) Å | Cell parameters from 14540 reflections |
b = 14.134 (3) Å | θ = 3.1–27.5° |
c = 15.655 (3) Å | µ = 0.47 mm−1 |
α = 110.51 (3)° | T = 295 K |
β = 90.95 (3)° | Block, yellow |
γ = 104.70 (3)° | 0.38 × 0.26 × 0.20 mm |
V = 1617.3 (8) Å3 |
Rigaku R-AXIS RAPID IP diffractometer | 5673 independent reflections |
Radiation source: fine-focus sealed tube | 3748 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
ω scans | θmax = 25.0°, θmin = 3.1° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −8→9 |
Tmin = 0.629, Tmax = 0.911 | k = −16→16 |
12644 measured reflections | l = −18→18 |
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)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.184 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.1002P)2 + 0.5697P] where P = (Fo2 + 2Fc2)/3 |
5673 reflections | (Δ/σ)max = 0.001 |
470 parameters | Δρmax = 0.58 e Å−3 |
80 restraints | Δρmin = −0.37 e Å−3 |
[Mn(C9H6O5)(C12H8N2)2(H2O)]·4H2O | γ = 104.70 (3)° |
Mr = 699.57 | V = 1617.3 (8) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.123 (2) Å | Mo Kα radiation |
b = 14.134 (3) Å | µ = 0.47 mm−1 |
c = 15.655 (3) Å | T = 295 K |
α = 110.51 (3)° | 0.38 × 0.26 × 0.20 mm |
β = 90.95 (3)° |
Rigaku R-AXIS RAPID IP diffractometer | 5673 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 3748 reflections with I > 2σ(I) |
Tmin = 0.629, Tmax = 0.911 | Rint = 0.041 |
12644 measured reflections |
R[F2 > 2σ(F2)] = 0.066 | 80 restraints |
wR(F2) = 0.184 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.58 e Å−3 |
5673 reflections | Δρmin = −0.37 e Å−3 |
470 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Mn1 | 0.21393 (8) | 0.26715 (4) | 0.25808 (4) | 0.0538 (2) | |
O1 | 0.4247 (4) | 0.3438 (2) | 0.2083 (2) | 0.064 (1) | |
O2 | 0.5954 (4) | 0.2380 (2) | 0.1689 (3) | 0.081 (1) | |
O3 | 0.6852 (5) | 0.6298 (3) | 0.0817 (3) | 0.099 (1) | |
O1w | 0.3542 (4) | 0.1530 (2) | 0.2520 (2) | 0.080 (1) | |
O2w | 0.308 (1) | 0.0358 (6) | 0.3592 (7) | 0.234 (4) | |
O3w | 0.205 (2) | −0.1812 (7) | 0.2507 (7) | 0.320 (6) | |
O4w | 0.475 (2) | 0.877 (1) | 0.4501 (13) | 0.416 (9) | |
O5w | 0.955 (2) | 0.8805 (5) | 0.4553 (5) | 0.277 (5) | |
N1 | 0.2696 (4) | 0.3477 (2) | 0.4129 (2) | 0.055 (1) | |
N2 | 0.1274 (4) | 0.4158 (2) | 0.2958 (2) | 0.056 (1) | |
N3 | 0.0654 (5) | 0.1943 (3) | 0.1147 (2) | 0.058 (1) | |
N4 | −0.0254 (4) | 0.1465 (2) | 0.2644 (2) | 0.057 (1) | |
C1 | 0.2428 (5) | 0.4446 (3) | 0.4472 (3) | 0.053 (1) | |
C2 | 0.3350 (6) | 0.3139 (4) | 0.4708 (3) | 0.068 (1) | |
C3 | 0.3758 (7) | 0.3702 (4) | 0.5639 (3) | 0.076 (1) | |
C4 | 0.3512 (6) | 0.4674 (4) | 0.5990 (3) | 0.079 (1) | |
C5 | 0.2840 (6) | 0.5086 (3) | 0.5410 (3) | 0.064 (1) | |
C6 | 0.2574 (7) | 0.6111 (4) | 0.5708 (4) | 0.084 (2) | |
C7 | 0.1912 (7) | 0.6463 (4) | 0.5130 (4) | 0.088 (2) | |
C8 | 0.1463 (6) | 0.5823 (3) | 0.4170 (3) | 0.066 (1) | |
C9 | 0.0740 (7) | 0.6142 (4) | 0.3535 (5) | 0.088 (2) | |
C10 | 0.0310 (7) | 0.5484 (4) | 0.2643 (4) | 0.087 (2) | |
C11 | 0.0590 (6) | 0.4493 (4) | 0.2388 (4) | 0.073 (1) | |
C12 | 0.1712 (5) | 0.4819 (3) | 0.3851 (3) | 0.054 (1) | |
C13 | −0.0780 (5) | 0.1140 (3) | 0.1040 (3) | 0.055 (1) | |
C14 | 0.1087 (6) | 0.2173 (4) | 0.0425 (3) | 0.065 (1) | |
C15 | 0.0170 (7) | 0.1645 (4) | −0.0452 (3) | 0.078 (1) | |
C16 | −0.1242 (7) | 0.0822 (4) | −0.0564 (3) | 0.077 (2) | |
C17 | −0.1768 (6) | 0.0546 (3) | 0.0178 (3) | 0.066 (1) | |
C18 | −0.3233 (7) | −0.0297 (4) | 0.0110 (4) | 0.078 (2) | |
C19 | −0.3704 (6) | −0.0509 (3) | 0.0859 (4) | 0.082 (2) | |
C20 | −0.2751 (6) | 0.0072 (3) | 0.1735 (4) | 0.064 (1) | |
C21 | −0.3172 (7) | −0.0124 (4) | 0.2525 (5) | 0.085 (2) | |
C22 | −0.2159 (7) | 0.0434 (4) | 0.3339 (4) | 0.085 (2) | |
C23 | −0.0684 (6) | 0.1230 (3) | 0.3374 (4) | 0.070 (1) | |
C24 | −0.1269 (5) | 0.0896 (3) | 0.1828 (3) | 0.055 (1) | |
C25 | 0.5460 (5) | 0.3131 (3) | 0.1665 (3) | 0.057 (1) | |
C26 | 0.6300 (5) | 0.3742 (3) | 0.1093 (3) | 0.059 (1) | |
C27 | 0.6149 (6) | 0.4746 (3) | 0.1244 (3) | 0.062 (1) | |
C28 | 0.6913 (6) | 0.5293 (4) | 0.0725 (4) | 0.075 (1) | |
C29 | 0.7789 (7) | 0.4819 (5) | 0.0015 (5) | 0.096 (2) | |
C30 | 0.7941 (7) | 0.3834 (5) | −0.0131 (4) | 0.097 (2) | |
C31 | 0.7216 (6) | 0.3294 (4) | 0.0402 (3) | 0.071 (1) | |
O4' | 0.927 (1) | 0.7319 (7) | 0.2157 (8) | 0.088 (3) | 0.44 (1) |
O5' | 0.730 (2) | 0.7828 (9) | 0.3093 (9) | 0.101 (5) | 0.44 (1) |
C32' | 0.616 (2) | 0.686 (2) | 0.157 (1) | 0.075 (8) | 0.44 (1) |
C33' | 0.776 (2) | 0.738 (1) | 0.2316 (9) | 0.073 (5) | 0.44 (1) |
O4 | 0.523 (2) | 0.7644 (7) | 0.3035 (7) | 0.150 (6) | 0.56 (1) |
O5 | 0.794 (3) | 0.741 (1) | 0.277 (1) | 0.144 (8) | 0.56 (1) |
C32 | 0.593 (3) | 0.682 (2) | 0.148 (1) | 0.13 (1) | 0.56 (1) |
C33 | 0.640 (2) | 0.736 (1) | 0.254 (1) | 0.111 (5) | 0.56 (1) |
H1w1 | 0.3510 | 0.1414 | 0.3017 | 0.096* | |
H1w2 | 0.4575 | 0.1769 | 0.2443 | 0.096* | |
H2w1 | 0.3104 | −0.0097 | 0.3046 | 0.281* | |
H2w2 | 0.3686 | 0.0239 | 0.3975 | 0.281* | |
H3w1 | 0.1271 | −0.1747 | 0.2136 | 0.383* | |
H3w2 | 0.1685 | −0.2483 | 0.2417 | 0.383* | |
H4w1 | 0.5343 | 0.8442 | 0.4098 | 0.499* | |
H4w2 | 0.3753 | 0.8281 | 0.4397 | 0.499* | |
H5w1 | 0.9031 | 0.8533 | 0.4004 | 0.332* | |
H5w2 | 0.8912 | 0.9198 | 0.4886 | 0.332* | |
H2 | 0.3548 | 0.2481 | 0.4473 | 0.082* | |
H3 | 0.4192 | 0.3420 | 0.6019 | 0.092* | |
H4 | 0.3788 | 0.5067 | 0.6615 | 0.095* | |
H6 | 0.2872 | 0.6546 | 0.6322 | 0.101* | |
H7 | 0.1739 | 0.7128 | 0.5351 | 0.106* | |
H9 | 0.0554 | 0.6804 | 0.3724 | 0.105* | |
H10 | −0.0159 | 0.5689 | 0.2213 | 0.104* | |
H11 | 0.0276 | 0.4041 | 0.1779 | 0.088* | |
H14 | 0.2064 | 0.2721 | 0.0499 | 0.078* | |
H15 | 0.0510 | 0.1847 | −0.0942 | 0.093* | |
H16 | −0.1857 | 0.0444 | −0.1142 | 0.093* | |
H18 | −0.3870 | −0.0705 | −0.0458 | 0.094* | |
H19 | −0.4682 | −0.1051 | 0.0800 | 0.098* | |
H21 | −0.4161 | −0.0644 | 0.2497 | 0.101* | |
H22 | −0.2438 | 0.0290 | 0.3863 | 0.102* | |
H23 | 0.0015 | 0.1605 | 0.3928 | 0.084* | |
H27 | 0.5521 | 0.5046 | 0.1704 | 0.075* | |
H29 | 0.8273 | 0.5174 | −0.0360 | 0.115* | |
H30 | 0.8545 | 0.3528 | −0.0600 | 0.116* | |
H31 | 0.7338 | 0.2628 | 0.0302 | 0.085* | |
H32c | 0.5257 | 0.6392 | 0.1752 | 0.090* | 0.44 (1) |
H32d | 0.5720 | 0.7380 | 0.1453 | 0.090* | 0.44 (1) |
H32a | 0.4820 | 0.6309 | 0.1387 | 0.158* | 0.56 (1) |
H32b | 0.5722 | 0.7358 | 0.1278 | 0.158* | 0.56 (1) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Mn1 | 0.0600 (4) | 0.0459 (3) | 0.0471 (4) | 0.0116 (3) | −0.0045 (3) | 0.0095 (3) |
O1 | 0.066 (2) | 0.052 (2) | 0.070 (2) | 0.019 (1) | 0.0134 (16) | 0.016 (1) |
O2 | 0.086 (2) | 0.067 (2) | 0.099 (3) | 0.034 (2) | 0.017 (2) | 0.033 (2) |
O3 | 0.101 (3) | 0.084 (3) | 0.120 (4) | 0.010 (2) | −0.007 (3) | 0.057 (3) |
O1w | 0.091 (2) | 0.072 (2) | 0.086 (2) | 0.034 (2) | 0.007 (2) | 0.032 (2) |
O2w | 0.221 (7) | 0.195 (6) | 0.40 (1) | 0.116 (6) | 0.100 (8) | 0.202 (8) |
O3w | 0.54 (2) | 0.209 (8) | 0.28 (1) | 0.13 (1) | 0.11 (1) | 0.144 (8) |
O4w | 0.47 (2) | 0.39 (2) | 0.57 (2) | 0.17 (2) | 0.16 (2) | 0.35 (2) |
O5w | 0.44 (1) | 0.169 (6) | 0.157 (6) | −0.015 (7) | −0.149 (7) | 0.059 (5) |
N1 | 0.056 (2) | 0.046 (2) | 0.053 (2) | 0.002 (2) | −0.006 (2) | 0.015 (2) |
N2 | 0.055 (2) | 0.056 (2) | 0.053 (2) | 0.013 (2) | −0.003 (2) | 0.016 (2) |
N3 | 0.063 (2) | 0.055 (2) | 0.052 (2) | 0.019 (2) | 0.001 (2) | 0.014 (2) |
N4 | 0.064 (2) | 0.047 (2) | 0.054 (2) | 0.014 (2) | −0.001 (2) | 0.013 (2) |
C1 | 0.047 (2) | 0.048 (2) | 0.051 (2) | 0.001 (2) | 0.006 (2) | 0.011 (2) |
C2 | 0.075 (3) | 0.062 (3) | 0.060 (3) | 0.001 (2) | −0.007 (2) | 0.026 (2) |
C3 | 0.083 (4) | 0.081 (3) | 0.060 (3) | −0.002 (3) | −0.009 (3) | 0.037 (3) |
C4 | 0.075 (3) | 0.089 (4) | 0.048 (3) | −0.004 (3) | −0.002 (2) | 0.014 (3) |
C5 | 0.059 (3) | 0.061 (3) | 0.051 (3) | 0.001 (2) | 0.005 (2) | 0.006 (2) |
C6 | 0.081 (4) | 0.071 (3) | 0.064 (3) | 0.008 (3) | 0.006 (3) | −0.010 (3) |
C7 | 0.081 (4) | 0.055 (3) | 0.098 (4) | 0.020 (3) | 0.007 (3) | −0.010 (3) |
C8 | 0.051 (3) | 0.052 (2) | 0.085 (3) | 0.014 (2) | 0.006 (2) | 0.014 (2) |
C9 | 0.069 (3) | 0.060 (3) | 0.126 (5) | 0.024 (3) | 0.001 (3) | 0.021 (3) |
C10 | 0.078 (4) | 0.077 (3) | 0.118 (5) | 0.030 (3) | −0.007 (3) | 0.046 (3) |
C11 | 0.074 (3) | 0.076 (3) | 0.071 (3) | 0.025 (2) | −0.006 (3) | 0.027 (3) |
C12 | 0.045 (2) | 0.047 (2) | 0.061 (3) | 0.009 (2) | 0.006 (2) | 0.014 (2) |
C13 | 0.061 (3) | 0.047 (2) | 0.055 (3) | 0.028 (2) | −0.001 (2) | 0.007 (2) |
C14 | 0.069 (3) | 0.071 (3) | 0.056 (3) | 0.025 (2) | 0.004 (2) | 0.020 (2) |
C15 | 0.096 (4) | 0.092 (4) | 0.051 (3) | 0.045 (3) | 0.003 (3) | 0.020 (3) |
C16 | 0.089 (4) | 0.082 (3) | 0.053 (3) | 0.047 (3) | −0.015 (3) | 0.002 (3) |
C17 | 0.069 (3) | 0.053 (2) | 0.065 (3) | 0.033 (2) | −0.014 (2) | 0.000 (2) |
C18 | 0.079 (4) | 0.055 (3) | 0.084 (4) | 0.026 (3) | −0.027 (3) | 0.002 (3) |
C19 | 0.064 (3) | 0.046 (2) | 0.115 (5) | 0.011 (2) | −0.025 (3) | 0.010 (3) |
C20 | 0.059 (3) | 0.044 (2) | 0.088 (4) | 0.017 (2) | −0.001 (3) | 0.020 (2) |
C21 | 0.074 (3) | 0.056 (3) | 0.119 (5) | 0.010 (2) | 0.004 (3) | 0.032 (3) |
C22 | 0.097 (4) | 0.073 (3) | 0.095 (4) | 0.017 (3) | 0.021 (3) | 0.046 (3) |
C23 | 0.083 (3) | 0.061 (3) | 0.067 (3) | 0.018 (2) | 0.007 (3) | 0.024 (2) |
C24 | 0.055 (2) | 0.040 (2) | 0.067 (3) | 0.020 (2) | −0.001 (2) | 0.011 (2) |
C25 | 0.056 (3) | 0.047 (2) | 0.055 (3) | 0.009 (2) | −0.008 (2) | 0.006 (2) |
C26 | 0.044 (2) | 0.057 (2) | 0.063 (3) | 0.011 (2) | −0.008 (2) | 0.010 (2) |
C27 | 0.055 (3) | 0.062 (2) | 0.063 (3) | 0.013 (2) | −0.005 (2) | 0.020 (2) |
C28 | 0.059 (3) | 0.078 (3) | 0.087 (4) | 0.006 (2) | −0.007 (3) | 0.041 (3) |
C29 | 0.072 (4) | 0.128 (5) | 0.102 (5) | 0.020 (3) | 0.019 (3) | 0.064 (4) |
C30 | 0.080 (4) | 0.120 (5) | 0.096 (4) | 0.038 (4) | 0.030 (3) | 0.037 (4) |
C31 | 0.059 (3) | 0.076 (3) | 0.075 (3) | 0.021 (2) | 0.007 (3) | 0.021 (3) |
O4' | 0.067 (6) | 0.099 (6) | 0.101 (8) | 0.023 (5) | −0.007 (5) | 0.042 (5) |
O5' | 0.12 (1) | 0.079 (8) | 0.09 (1) | 0.002 (7) | −0.017 (8) | 0.043 (7) |
C32' | 0.09 (1) | 0.05 (1) | 0.09 (2) | 0.025 (9) | 0.01 (1) | 0.03 (1) |
C33' | 0.09 (1) | 0.051 (7) | 0.09 (1) | 0.006 (7) | −0.016 (10) | 0.043 (9) |
O4 | 0.25 (2) | 0.098 (6) | 0.095 (7) | 0.021 (7) | −0.012 (8) | 0.050 (5) |
O5 | 0.20 (2) | 0.080 (7) | 0.13 (1) | 0.017 (8) | −0.07 (1) | 0.033 (8) |
C32 | 0.20 (2) | 0.09 (2) | 0.11 (2) | 0.048 (15) | −0.05 (1) | 0.03 (1) |
C33 | 0.16 (2) | 0.072 (8) | 0.11 (1) | 0.01 (1) | −0.01 (1) | 0.060 (9) |
Mn1—O1 | 2.099 (3) | C26—C27 | 1.393 (6) |
Mn1—O1w | 2.177 (3) | C27—C28 | 1.363 (7) |
Mn1—N1 | 2.268 (3) | C28—C29 | 1.391 (8) |
Mn1—N2 | 2.269 (3) | C29—C30 | 1.368 (8) |
Mn1—N3 | 2.284 (4) | C30—C31 | 1.364 (8) |
Mn1—N4 | 2.267 (4) | O4'—C33' | 1.273 (11) |
O1—C25 | 1.276 (5) | O5'—C33' | 1.273 (10) |
O2—C25 | 1.239 (5) | C32'—C33' | 1.565 (15) |
O3—C32' | 1.387 (10) | O4—C33 | 1.283 (10) |
O3—C28 | 1.391 (6) | O5—C33 | 1.277 (10) |
O3—C32 | 1.391 (10) | C32—C33 | 1.570 (14) |
N1—C2 | 1.322 (5) | O1w—H1w1 | 0.85 |
N1—C1 | 1.360 (5) | O1w—H1w2 | 0.85 |
N2—C11 | 1.320 (5) | O2w—H2w1 | 0.88 |
N2—C12 | 1.362 (5) | O2w—H2w2 | 0.86 |
N3—C14 | 1.311 (6) | O3w—H3w1 | 0.90 |
N3—C13 | 1.364 (5) | O3w—H3w2 | 0.88 |
N4—C23 | 1.326 (6) | O4w—H4w1 | 0.87 |
N4—C24 | 1.367 (5) | O4w—H4w2 | 0.89 |
C1—C5 | 1.410 (6) | O5w—H5w1 | 0.86 |
C1—C12 | 1.434 (6) | O5w—H5w2 | 0.90 |
C2—C3 | 1.381 (7) | C2—H2 | 0.93 |
C3—C4 | 1.358 (7) | C3—H3 | 0.93 |
C4—C5 | 1.406 (7) | C4—H4 | 0.93 |
C5—C6 | 1.433 (7) | C6—H6 | 0.93 |
C6—C7 | 1.338 (8) | C7—H7 | 0.93 |
C7—C8 | 1.439 (7) | C9—H9 | 0.93 |
C8—C12 | 1.400 (6) | C10—H10 | 0.93 |
C8—C9 | 1.402 (7) | C11—H11 | 0.93 |
C9—C10 | 1.359 (8) | C14—H14 | 0.93 |
C10—C11 | 1.396 (7) | C15—H15 | 0.93 |
C13—C17 | 1.414 (6) | C16—H16 | 0.93 |
C13—C24 | 1.428 (6) | C18—H18 | 0.93 |
C14—C15 | 1.401 (6) | C19—H19 | 0.93 |
C15—C16 | 1.368 (7) | C21—H21 | 0.93 |
C16—C17 | 1.391 (7) | C22—H22 | 0.93 |
C17—C18 | 1.427 (7) | C23—H23 | 0.93 |
C18—C19 | 1.346 (8) | C27—H27 | 0.93 |
C19—C20 | 1.417 (7) | C29—H29 | 0.93 |
C20—C21 | 1.389 (7) | C30—H30 | 0.93 |
C20—C24 | 1.411 (6) | C31—H31 | 0.93 |
C21—C22 | 1.363 (8) | C32'—H32c | 0.97 |
C22—C23 | 1.406 (7) | C32'—H32d | 0.97 |
C25—C26 | 1.507 (6) | C32—H32a | 0.97 |
C26—C31 | 1.382 (6) | C32—H32b | 0.97 |
O1—Mn1—O1w | 86.5 (1) | O1—C25—C26 | 115.5 (4) |
O1—Mn1—N1 | 104.3 (1) | C31—C26—C27 | 119.5 (5) |
O1—Mn1—N2 | 87.4 (1) | C31—C26—C25 | 119.6 (4) |
O1—Mn1—N3 | 90.4 (1) | C27—C26—C25 | 120.9 (4) |
O1—Mn1—N4 | 161.3 (1) | C28—C27—C26 | 120.5 (5) |
O1w—Mn1—N1 | 93.9 (1) | C27—C28—O3 | 125.4 (5) |
O1w—Mn1—N2 | 164.1 (1) | C27—C28—C29 | 119.2 (5) |
O1w—Mn1—N3 | 101.1 (1) | O3—C28—C29 | 115.3 (5) |
O1w—Mn1—N4 | 87.5 (1) | C30—C29—C28 | 120.2 (6) |
N1—Mn1—N2 | 73.4 (1) | C31—C30—C29 | 120.9 (5) |
N1—Mn1—N3 | 159.7 (1) | C30—C31—C26 | 119.7 (5) |
N1—Mn1—N4 | 93.8 (1) | O3—C32'—C33' | 101.5 (9) |
N2—Mn1—N3 | 93.7 (1) | O4'—C33'—O5' | 126.2 (15) |
N2—Mn1—N4 | 102.6 (1) | O4'—C33'—C32' | 124.3 (10) |
N3—Mn1—N4 | 73.5 (1) | O5'—C33'—C32' | 109.5 (12) |
C25—O1—Mn1 | 132.5 (3) | O3—C32—C33 | 129.3 (15) |
C32'—O3—C28 | 118.0 (13) | O5—C33—O4 | 131.3 (19) |
C28—O3—C32 | 119.7 (16) | O5—C33—C32 | 110.1 (17) |
C2—N1—C1 | 117.8 (4) | O4—C33—C32 | 118.5 (11) |
C2—N1—Mn1 | 127.2 (3) | Mn1—O1w—H1w1 | 109.5 |
C1—N1—Mn1 | 114.8 (3) | Mn1—O1w—H1w2 | 109.4 |
C11—N2—C12 | 117.7 (4) | H1w1—O1w—H1w2 | 109.8 |
C11—N2—Mn1 | 126.8 (3) | H2w1—O2w—H2w2 | 107.4 |
C12—N2—Mn1 | 115.0 (3) | H3w1—O3w—H3w2 | 101.4 |
C14—N3—C13 | 118.2 (4) | H4w1—O4w—H4w2 | 102.3 |
C14—N3—Mn1 | 127.1 (3) | H5w1—O5w—H5w2 | 105.0 |
C13—N3—Mn1 | 114.6 (3) | N1—C2—H2 | 117.9 |
C23—N4—C24 | 118.5 (4) | C3—C2—H2 | 117.9 |
C23—N4—Mn1 | 126.2 (3) | C4—C3—H3 | 120.7 |
C24—N4—Mn1 | 115.2 (3) | C2—C3—H3 | 120.7 |
N1—C1—C5 | 122.0 (4) | C3—C4—H4 | 119.9 |
N1—C1—C12 | 118.3 (3) | C5—C4—H4 | 119.9 |
C5—C1—C12 | 119.7 (4) | C7—C6—H6 | 118.9 |
N1—C2—C3 | 124.2 (5) | C5—C6—H6 | 118.9 |
C4—C3—C2 | 118.6 (5) | C6—C7—H7 | 119.6 |
C3—C4—C5 | 120.1 (4) | C8—C7—H7 | 119.6 |
C4—C5—C1 | 117.2 (4) | C10—C9—H9 | 120.0 |
C4—C5—C6 | 124.4 (5) | C8—C9—H9 | 120.0 |
C1—C5—C6 | 118.3 (5) | N2—C11—H11 | 118.0 |
C7—C6—C5 | 122.1 (5) | C10—C11—H11 | 118.0 |
C6—C7—C8 | 120.8 (5) | N3—C14—H14 | 117.9 |
C12—C8—C9 | 117.8 (4) | C15—C14—H14 | 117.9 |
C12—C8—C7 | 118.8 (5) | C16—C15—H15 | 121.1 |
C9—C8—C7 | 123.4 (5) | C14—C15—H15 | 121.1 |
C10—C9—C8 | 120.0 (5) | C15—C16—H16 | 119.7 |
C9—C10—C11 | 118.2 (5) | C17—C16—H16 | 119.7 |
C9—C10—H10 | 120.9 | C19—C18—H18 | 119.6 |
C11—C10—H10 | 120.9 | C17—C18—H18 | 119.6 |
N2—C11—C10 | 124.1 (5) | C18—C19—H19 | 119.1 |
N2—C12—C8 | 122.2 (4) | C20—C19—H19 | 119.1 |
N2—C12—C1 | 117.6 (3) | C22—C21—H21 | 119.5 |
C8—C12—C1 | 120.2 (4) | C20—C21—H21 | 119.5 |
N3—C13—C17 | 121.9 (4) | C21—C22—H22 | 120.6 |
N3—C13—C24 | 118.3 (4) | C23—C22—H22 | 120.6 |
C17—C13—C24 | 119.8 (4) | N4—C23—H23 | 118.8 |
N3—C14—C15 | 124.1 (5) | C22—C23—H23 | 118.8 |
C16—C15—C14 | 117.7 (5) | C28—C27—H27 | 119.7 |
C15—C16—C17 | 120.7 (4) | C26—C27—H27 | 119.7 |
C16—C17—C13 | 117.4 (5) | C30—C29—H29 | 119.9 |
C16—C17—C18 | 123.5 (5) | C28—C29—H29 | 119.9 |
C13—C17—C18 | 119.1 (5) | C31—C30—H30 | 119.6 |
C19—C18—C17 | 120.7 (5) | C29—C30—H30 | 119.6 |
C18—C19—C20 | 121.8 (5) | C30—C31—H31 | 120.2 |
C21—C20—C24 | 116.8 (4) | C26—C31—H31 | 120.2 |
C21—C20—C19 | 123.9 (5) | O3—C32'—H32c | 111.5 |
C24—C20—C19 | 119.3 (5) | C33'—C32'—H32c | 111.5 |
C22—C21—C20 | 121.1 (5) | O3—C32'—H32d | 111.5 |
C21—C22—C23 | 118.8 (5) | C33'—C32'—H32d | 111.5 |
N4—C23—C22 | 122.3 (5) | H32c—C32'—H32d | 109.3 |
N4—C24—C20 | 122.5 (4) | O3—C32—H32a | 105.0 |
N4—C24—C13 | 118.2 (4) | C33—C32—H32a | 105.0 |
C20—C24—C13 | 119.3 (4) | O3—C32—H32b | 105.0 |
O2—C25—O1 | 124.9 (4) | C33—C32—H32b | 105.0 |
O2—C25—C26 | 119.5 (4) | H32a—C32—H32b | 105.8 |
O1w—Mn1—O1—C25 | 19.5 (4) | C9—C8—C12—N2 | −0.1 (7) |
N4—Mn1—O1—C25 | −52.0 (6) | C7—C8—C12—N2 | 178.2 (4) |
N1—Mn1—O1—C25 | 112.6 (4) | C9—C8—C12—C1 | −179.3 (4) |
N2—Mn1—O1—C25 | −175.3 (4) | C7—C8—C12—C1 | −1.0 (6) |
N3—Mn1—O1—C25 | −81.6 (4) | N1—C1—C12—N2 | 2.8 (6) |
O1—Mn1—N1—C2 | −99.0 (4) | C5—C1—C12—N2 | −177.6 (4) |
O1w—Mn1—N1—C2 | −11.6 (4) | N1—C1—C12—C8 | −178.1 (4) |
N4—Mn1—N1—C2 | 76.1 (4) | C5—C1—C12—C8 | 1.6 (6) |
N2—Mn1—N1—C2 | 178.2 (4) | C14—N3—C13—C17 | 1.5 (5) |
N3—Mn1—N1—C2 | 126.1 (4) | Mn1—N3—C13—C17 | −174.7 (3) |
O1—Mn1—N1—C1 | 76.1 (3) | C14—N3—C13—C24 | −179.2 (3) |
O1w—Mn1—N1—C1 | 163.5 (3) | Mn1—N3—C13—C24 | 4.6 (4) |
N4—Mn1—N1—C1 | −108.8 (3) | C13—N3—C14—C15 | −0.1 (6) |
N2—Mn1—N1—C1 | −6.7 (3) | Mn1—N3—C14—C15 | 175.6 (3) |
N3—Mn1—N1—C1 | −58.9 (5) | N3—C14—C15—C16 | −1.6 (7) |
O1—Mn1—N2—C11 | 73.9 (4) | C14—C15—C16—C17 | 1.9 (7) |
O1w—Mn1—N2—C11 | 141.5 (5) | C15—C16—C17—C13 | −0.6 (6) |
N4—Mn1—N2—C11 | −90.2 (4) | C15—C16—C17—C18 | 179.6 (4) |
N1—Mn1—N2—C11 | 179.6 (4) | N3—C13—C17—C16 | −1.2 (6) |
N3—Mn1—N2—C11 | −16.3 (4) | C24—C13—C17—C16 | 179.5 (3) |
O1—Mn1—N2—C12 | −97.5 (3) | N3—C13—C17—C18 | 178.7 (3) |
O1w—Mn1—N2—C12 | −29.9 (6) | C24—C13—C17—C18 | −0.6 (5) |
N4—Mn1—N2—C12 | 98.4 (3) | C16—C17—C18—C19 | −178.2 (4) |
N1—Mn1—N2—C12 | 8.2 (3) | C13—C17—C18—C19 | 1.9 (6) |
N3—Mn1—N2—C12 | 172.3 (3) | C17—C18—C19—C20 | −1.7 (7) |
O1—Mn1—N3—C14 | −9.7 (3) | C18—C19—C20—C21 | −179.2 (4) |
O1w—Mn1—N3—C14 | −96.2 (3) | C18—C19—C20—C24 | 0.1 (6) |
N4—Mn1—N3—C14 | 179.8 (4) | C24—C20—C21—C22 | −2.2 (7) |
N1—Mn1—N3—C14 | 127.0 (4) | C19—C20—C21—C22 | 177.1 (4) |
N2—Mn1—N3—C14 | 77.7 (3) | C20—C21—C22—C23 | 1.1 (8) |
O1—Mn1—N3—C13 | 166.1 (3) | C24—N4—C23—C22 | −1.3 (6) |
O1w—Mn1—N3—C13 | 79.6 (3) | Mn1—N4—C23—C22 | −176.9 (3) |
N4—Mn1—N3—C13 | −4.4 (2) | C21—C22—C23—N4 | 0.7 (7) |
N1—Mn1—N3—C13 | −57.2 (5) | C23—N4—C24—C20 | 0.1 (5) |
N2—Mn1—N3—C13 | −106.4 (3) | Mn1—N4—C24—C20 | 176.2 (3) |
O1—Mn1—N4—C23 | 148.4 (4) | C23—N4—C24—C13 | −178.8 (3) |
O1w—Mn1—N4—C23 | 77.1 (3) | Mn1—N4—C24—C13 | −2.7 (4) |
N1—Mn1—N4—C23 | −16.6 (3) | C21—C20—C24—N4 | 1.6 (6) |
N2—Mn1—N4—C23 | −90.5 (3) | C19—C20—C24—N4 | −177.7 (4) |
N3—Mn1—N4—C23 | 179.4 (4) | C21—C20—C24—C13 | −179.5 (4) |
O1—Mn1—N4—C24 | −27.4 (5) | C19—C20—C24—C13 | 1.2 (5) |
O1w—Mn1—N4—C24 | −98.7 (3) | N3—C13—C24—N4 | −1.3 (5) |
N1—Mn1—N4—C24 | 167.6 (3) | C17—C13—C24—N4 | 178.0 (3) |
N2—Mn1—N4—C24 | 93.8 (3) | N3—C13—C24—C20 | 179.7 (3) |
N3—Mn1—N4—C24 | 3.7 (2) | C17—C13—C24—C20 | −0.9 (5) |
C2—N1—C1—C5 | 0.6 (6) | Mn1—O1—C25—O2 | −22.8 (6) |
Mn1—N1—C1—C5 | −174.9 (3) | Mn1—O1—C25—C26 | 156.2 (3) |
C2—N1—C1—C12 | −179.7 (4) | O2—C25—C26—C31 | 19.3 (6) |
Mn1—N1—C1—C12 | 4.7 (4) | O1—C25—C26—C31 | −159.6 (4) |
C1—N1—C2—C3 | 0.8 (7) | O2—C25—C26—C27 | −161.5 (4) |
Mn1—N1—C2—C3 | 175.8 (4) | O1—C25—C26—C27 | 19.6 (5) |
N1—C2—C3—C4 | −1.4 (8) | C31—C26—C27—C28 | −0.8 (6) |
C2—C3—C4—C5 | 0.6 (7) | C25—C26—C27—C28 | 180.0 (4) |
C3—C4—C5—C1 | 0.7 (7) | C26—C27—C28—O3 | −179.7 (4) |
C3—C4—C5—C6 | −178.3 (5) | C26—C27—C28—C29 | 2.6 (7) |
N1—C1—C5—C4 | −1.3 (6) | C32'—O3—C28—C27 | 9.2 (10) |
C12—C1—C5—C4 | 179.0 (4) | C32—O3—C28—C27 | −1.1 (12) |
N1—C1—C5—C6 | 177.7 (4) | C32'—O3—C28—C29 | −173.1 (9) |
C12—C1—C5—C6 | −2.0 (6) | C32—O3—C28—C29 | 176.6 (11) |
C4—C5—C6—C7 | −179.2 (5) | C27—C28—C29—C30 | −2.8 (8) |
C1—C5—C6—C7 | 1.8 (8) | O3—C28—C29—C30 | 179.4 (5) |
C5—C6—C7—C8 | −1.2 (9) | C28—C29—C30—C31 | 1.1 (9) |
C6—C7—C8—C12 | 0.8 (8) | C29—C30—C31—C26 | 0.7 (8) |
C6—C7—C8—C9 | 179.0 (5) | C27—C26—C31—C30 | −0.9 (7) |
C12—C8—C9—C10 | −0.2 (8) | C25—C26—C31—C30 | 178.3 (5) |
C7—C8—C9—C10 | −178.4 (5) | C28—O3—C32'—C33' | 86.1 (16) |
C8—C9—C10—C11 | 0.7 (8) | C32—O3—C32'—C33' | −171 (18) |
C12—N2—C11—C10 | 0.8 (7) | O3—C32'—C33'—O4' | 5 (3) |
Mn1—N2—C11—C10 | −170.4 (4) | O3—C32'—C33'—O5' | −172.4 (15) |
C9—C10—C11—N2 | −1.1 (8) | C32'—O3—C32—C33 | −6 (14) |
C11—N2—C12—C8 | −0.2 (6) | C28—O3—C32—C33 | 75 (3) |
Mn1—N2—C12—C8 | 172.1 (3) | O3—C32—C33—O5 | 10 (4) |
C11—N2—C12—C1 | 179.0 (4) | O3—C32—C33—O4 | −169 (2) |
Mn1—N2—C12—C1 | −8.8 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H1w1···O2w | 0.85 | 1.96 | 2.712 (7) | 147 |
O1w—H1w2···O2 | 0.85 | 1.91 | 2.638 (5) | 143 |
O2w—H2w1···O3w | 0.88 | 2.19 | 2.83 (1) | 129 |
O3w—H3w1···O4′i | 0.90 | 1.82 | 2.23 (2) | 105 |
O4w—H4w1···O4 | 0.87 | 1.64 | 2.39 (2) | 144 |
O5w—H5w1···O5′ | 0.86 | 1.80 | 2.62 (2) | 159 |
Symmetry code: (i) x−1, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | [Mn(C9H6O5)(C12H8N2)2(H2O)]·4H2O |
Mr | 699.57 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 8.123 (2), 14.134 (3), 15.655 (3) |
α, β, γ (°) | 110.51 (3), 90.95 (3), 104.70 (3) |
V (Å3) | 1617.3 (8) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.47 |
Crystal size (mm) | 0.38 × 0.26 × 0.20 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID IP diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.629, 0.911 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12644, 5673, 3748 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.184, 1.02 |
No. of reflections | 5673 |
No. of parameters | 470 |
No. of restraints | 80 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.58, −0.37 |
Computer programs: RAPID-AUTO (Rigaku, 1998), RAPID-AUTO, CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97.
Mn1—O1 | 2.099 (3) | Mn1—N2 | 2.269 (3) |
Mn1—O1w | 2.177 (3) | Mn1—N3 | 2.284 (4) |
Mn1—N1 | 2.268 (3) | Mn1—N4 | 2.267 (4) |
O1—Mn1—O1w | 86.5 (1) | O1w—Mn1—N4 | 87.5 (1) |
O1—Mn1—N1 | 104.3 (1) | N1—Mn1—N2 | 73.4 (1) |
O1—Mn1—N2 | 87.4 (1) | N1—Mn1—N3 | 159.7 (1) |
O1—Mn1—N3 | 90.4 (1) | N1—Mn1—N4 | 93.8 (1) |
O1—Mn1—N4 | 161.3 (1) | N2—Mn1—N3 | 93.7 (1) |
O1w—Mn1—N1 | 93.9 (1) | N2—Mn1—N4 | 102.6 (1) |
O1w—Mn1—N2 | 164.1 (1) | N3—Mn1—N4 | 73.5 (1) |
O1w—Mn1—N3 | 101.1 (1) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H1w1···O2w | 0.85 | 1.96 | 2.712 (7) | 147 |
O1w—H1w2···O2 | 0.85 | 1.91 | 2.638 (5) | 143 |
O2w—H2w1···O3w | 0.88 | 2.19 | 2.83 (1) | 129 |
O3w—H3w1···O4'i | 0.90 | 1.82 | 2.23 (2) | 105 |
O4w—H4w1···O4 | 0.87 | 1.64 | 2.39 (2) | 144 |
O5w—H5w1···O5' | 0.86 | 1.80 | 2.62 (2) | 159 |
Symmetry code: (i) x−1, y−1, z. |
The carboxyphenoxyacetate ligand is a multidentate ligand with both rigid and flexible parts. As part of an investigation of carboxyphenoxyacetate complexes, we present here the X-ray structure of the title MnII complex, (I).
The molecular structure of (I) is shown in Fig. 1. The bis(phenanthroline)-chelated MnII complex of 3-carboxylphenoxyacetate exists as a monoaqua-coordinated tetrahydrate. The octahedral coordination geometry around the MnII atom is similar to that in the bis(phenanthroline)-chelated MnII complex with 4-carboxyphenoxyacetate (Huo et al., 2005). The 3-carboxylphenoxyacetate dianion coordinates in a monodentate fashion to the MnII atom through the carboxyl group on the benzene ring. The carboxyl group of the oxyacetate arm is free from coordination, but it engages in hydrogen-bonding interactions (Table 2). The two coordinated O atoms are cis to each other. The coordinated bond distances and angles are normal compared with those for reported related structures. Extensive hydrogen bonds (Table 2) lead to a three-dimensional network.