Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680705218X/ci2488sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680705218X/ci2488Isup2.hkl |
CCDC reference: 667243
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- R factor = 0.033
- wR factor = 0.089
- Data-to-parameter ratio = 16.5
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.624 0.880 Tmin(prime) and Tmax expected: 0.770 0.877 RR(prime) = 0.808 Please check that your absorption correction is appropriate. STRVA01_ALERT_4_C Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.360 From the CIF: _refine_ls_abs_structure_Flack_su 0.020 PLAT033_ALERT_2_C Flack Parameter Value Deviates 2 * su from zero. 0.36 PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.80 PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.40 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.46 From the CIF: _reflns_number_total 4362 Count of symmetry unique reflns 2510 Completeness (_total/calc) 173.78% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1852 Fraction of Friedel pairs measured 0.738 Are heavy atom types Z>Si present yes PLAT794_ALERT_5_G Check Predicted Bond Valency for Mn1 (9) 0.80 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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 3 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level G PUBL013_ALERT_1_G The _publ_section_comment (discussion of study) is missing. This is required for a full paper submission (but is optional for an electronic paper).
0 ALERT level A = Data missing that is essential or data in wrong format 1 ALERT level G = General alerts. Data that may be required is missing
Manganese dichloride hexahydrate (2 mmol), 3-(4-carboxylatophenoxy)propionic acid (2 mmol) and 2,2'-bipyridine (2 mmol) were dissolved in a 3:1 ethanol–water solution. Aqueous 0.1 M sodium hydroxide was added until the solution registered a pH of 7. The solution was set aside for the growth of crystal over several days. CH&N analysis. Calc. for C20H18N2O6Mn: C 54.93, H 4.15, N 6.41%. Found: C 54.94, H 4.13, N 6.42%.
The C-bound H atoms were placed in calculated positions [C—H = 0.93–0.97 Å and Uiso(H) = 1.2–1.5Ueq(C)], and were included in the refinement in the riding-model approximation. The water H-atoms were located in a difference Fourier map, and were refined with a distance restraint of O—H = 0.85 (1) Å; their Uiso(H) values were freely refined.
For the structure of 3-(4-carboxyphenoxy)propionic acid, see: Gao & Ng (2006). For the crystal structure of a CoII complex with the 3-(4-carboxylatophenoxy)propionate dianion, see: Xiao et al. (2006).
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); 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: X-SEED (Barbour, 2001) and OLEX (Dolomanov et al., 2003); software used to prepare material for publication: publCIF (Westrip, 2007).
[Mn(C10H8N2)(C10H8O5)(H2O)] | F(000) = 900 |
Mr = 437.30 | Dx = 1.517 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 13538 reflections |
a = 6.7770 (3) Å | θ = 3.0–27.5° |
b = 16.2626 (6) Å | µ = 0.73 mm−1 |
c = 17.3730 (5) Å | T = 295 K |
V = 1914.71 (12) Å3 | Prism, yellow |
Z = 4 | 0.35 × 0.29 × 0.18 mm |
Rigaku R-AXIS RAPID diffractometer | 4362 independent reflections |
Radiation source: fine-focus sealed tube | 3057 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
Detector resolution: 10.000 pixels mm-1 | θmax = 27.5°, θmin = 3.2° |
ω scans | h = −8→8 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −21→21 |
Tmin = 0.624, Tmax = 0.880 | l = −22→22 |
18852 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)] = 0.033 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.089 | w = 1/[σ2(Fo2) + (0.0533P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.95 | (Δ/σ)max = 0.001 |
4362 reflections | Δρmax = 0.34 e Å−3 |
264 parameters | Δρmin = −0.30 e Å−3 |
2 restraints | Absolute structure: Flack (1983), with 1860 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.36 (2) |
[Mn(C10H8N2)(C10H8O5)(H2O)] | V = 1914.71 (12) Å3 |
Mr = 437.30 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 6.7770 (3) Å | µ = 0.73 mm−1 |
b = 16.2626 (6) Å | T = 295 K |
c = 17.3730 (5) Å | 0.35 × 0.29 × 0.18 mm |
Rigaku R-AXIS RAPID diffractometer | 4362 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 3057 reflections with I > 2σ(I) |
Tmin = 0.624, Tmax = 0.880 | Rint = 0.042 |
18852 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.089 | Δρmax = 0.34 e Å−3 |
S = 0.95 | Δρmin = −0.30 e Å−3 |
4362 reflections | Absolute structure: Flack (1983), with 1860 Friedel pairs |
264 parameters | Absolute structure parameter: 0.36 (2) |
2 restraints |
x | y | z | Uiso*/Ueq | ||
Mn1 | 0.75683 (7) | 0.39945 (2) | 0.849961 (18) | 0.03710 (11) | |
O1 | 0.8310 (3) | 0.52190 (13) | 0.86239 (14) | 0.0622 (6) | |
O2 | 0.5582 (4) | 0.59275 (14) | 0.84588 (16) | 0.0803 (7) | |
O3 | 0.9809 (3) | 0.64933 (14) | 0.98274 (10) | 0.0552 (6) | |
O4 | 1.4164 (3) | 0.61980 (12) | 1.30356 (9) | 0.0430 (4) | |
O5 | 1.6748 (3) | 0.61228 (13) | 1.22776 (9) | 0.0459 (5) | |
O1W | 0.4470 (3) | 0.43660 (15) | 0.85866 (13) | 0.0520 (5) | |
H1W1 | 0.334 (2) | 0.4252 (19) | 0.8405 (17) | 0.063 (10)* | |
H1W2 | 0.459 (9) | 0.4888 (8) | 0.853 (3) | 0.16 (2)* | |
N1 | 0.7321 (4) | 0.26198 (12) | 0.86540 (11) | 0.0413 (5) | |
N2 | 0.7755 (4) | 0.37423 (14) | 0.97641 (10) | 0.0416 (5) | |
C1 | 0.7385 (5) | 0.58737 (15) | 0.85466 (13) | 0.0463 (6) | |
C2 | 0.8625 (5) | 0.66545 (18) | 0.85678 (16) | 0.0540 (8) | |
H2A | 0.8992 | 0.6800 | 0.8046 | 0.065* | |
H2B | 0.7827 | 0.7099 | 0.8773 | 0.065* | |
C3 | 1.0480 (5) | 0.65767 (19) | 0.90479 (14) | 0.0494 (7) | |
H3A | 1.1236 | 0.6098 | 0.8893 | 0.059* | |
H3B | 1.1300 | 0.7062 | 0.8992 | 0.059* | |
C4 | 1.1170 (4) | 0.64004 (19) | 1.04023 (15) | 0.0434 (8) | |
C5 | 1.3162 (4) | 0.6315 (2) | 1.02968 (15) | 0.0447 (8) | |
H5 | 1.3696 | 0.6316 | 0.9804 | 0.054* | |
C6 | 1.4373 (4) | 0.62257 (17) | 1.09374 (14) | 0.0391 (6) | |
H6 | 1.5725 | 0.6161 | 1.0868 | 0.047* | |
C7 | 1.3603 (4) | 0.62311 (19) | 1.16835 (14) | 0.0360 (6) | |
C8 | 1.1573 (4) | 0.6318 (2) | 1.17619 (15) | 0.0469 (9) | |
H8 | 1.1020 | 0.6323 | 1.2252 | 0.056* | |
C9 | 1.0369 (4) | 0.6398 (2) | 1.11337 (16) | 0.0506 (8) | |
H9 | 0.9013 | 0.6450 | 1.1199 | 0.061* | |
C10 | 1.4908 (4) | 0.61775 (16) | 1.23693 (13) | 0.0363 (6) | |
C11 | 0.7252 (5) | 0.20784 (18) | 0.80691 (16) | 0.0535 (7) | |
H11 | 0.7117 | 0.2280 | 0.7571 | 0.064* | |
C12 | 0.7371 (6) | 0.12452 (18) | 0.8171 (2) | 0.0664 (8) | |
H12 | 0.7305 | 0.0889 | 0.7753 | 0.080* | |
C13 | 0.7589 (5) | 0.09507 (19) | 0.8902 (2) | 0.0682 (9) | |
H13 | 0.7694 | 0.0388 | 0.8986 | 0.082* | |
C14 | 0.7654 (5) | 0.14913 (17) | 0.95166 (18) | 0.0583 (7) | |
H14 | 0.7786 | 0.1296 | 1.0017 | 0.070* | |
C15 | 0.7520 (5) | 0.23271 (14) | 0.93762 (14) | 0.0423 (5) | |
C16 | 0.7595 (4) | 0.29574 (16) | 0.99965 (13) | 0.0422 (6) | |
C17 | 0.7479 (5) | 0.2761 (2) | 1.07716 (14) | 0.0574 (7) | |
H17 | 0.7367 | 0.2216 | 1.0928 | 0.069* | |
C18 | 0.7533 (6) | 0.3384 (3) | 1.13051 (15) | 0.0713 (10) | |
H18 | 0.7459 | 0.3262 | 1.1827 | 0.086* | |
C19 | 0.7696 (5) | 0.4191 (2) | 1.10699 (16) | 0.0672 (9) | |
H19 | 0.7728 | 0.4618 | 1.1426 | 0.081* | |
C20 | 0.7808 (5) | 0.4344 (2) | 1.02932 (15) | 0.0547 (8) | |
H20 | 0.7924 | 0.4886 | 1.0128 | 0.066* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Mn1 | 0.03402 (19) | 0.04224 (19) | 0.03503 (17) | −0.0002 (2) | 0.0009 (2) | 0.00125 (15) |
O1 | 0.0507 (13) | 0.0422 (11) | 0.0939 (16) | −0.0024 (10) | −0.0079 (12) | −0.0035 (11) |
O2 | 0.0593 (15) | 0.0597 (14) | 0.122 (2) | 0.0052 (12) | −0.0319 (15) | −0.0050 (15) |
O3 | 0.0416 (12) | 0.0877 (16) | 0.0365 (9) | −0.0032 (11) | −0.0105 (8) | 0.0006 (9) |
O4 | 0.0323 (10) | 0.0623 (12) | 0.0345 (9) | −0.0020 (9) | −0.0001 (7) | −0.0047 (9) |
O5 | 0.0272 (9) | 0.0720 (13) | 0.0384 (8) | −0.0008 (9) | −0.0003 (7) | −0.0006 (9) |
O1W | 0.0320 (11) | 0.0665 (14) | 0.0575 (12) | −0.0004 (10) | −0.0075 (10) | −0.0060 (11) |
N1 | 0.0358 (12) | 0.0418 (11) | 0.0463 (11) | −0.0026 (12) | 0.0065 (11) | 0.0015 (8) |
N2 | 0.0355 (13) | 0.0551 (13) | 0.0343 (10) | 0.0031 (12) | −0.0014 (10) | 0.0001 (9) |
C1 | 0.0552 (16) | 0.0467 (15) | 0.0372 (11) | 0.0002 (18) | −0.0109 (17) | 0.0007 (10) |
C2 | 0.067 (2) | 0.0483 (17) | 0.0465 (15) | −0.0065 (15) | −0.0132 (16) | 0.0111 (14) |
C3 | 0.0527 (18) | 0.0541 (18) | 0.0415 (14) | −0.0061 (15) | −0.0048 (13) | 0.0042 (13) |
C4 | 0.0365 (16) | 0.053 (2) | 0.0410 (15) | −0.0059 (14) | −0.0084 (12) | −0.0012 (13) |
C5 | 0.0441 (18) | 0.0559 (19) | 0.0340 (13) | −0.0014 (13) | 0.0012 (11) | −0.0039 (12) |
C6 | 0.0301 (14) | 0.0441 (17) | 0.0430 (14) | 0.0004 (12) | −0.0002 (11) | −0.0040 (13) |
C7 | 0.0324 (14) | 0.0366 (15) | 0.0390 (14) | −0.0029 (12) | −0.0028 (10) | −0.0005 (12) |
C8 | 0.0320 (15) | 0.072 (2) | 0.0369 (14) | −0.0050 (15) | 0.0030 (12) | 0.0040 (14) |
C9 | 0.0287 (15) | 0.078 (2) | 0.0450 (15) | −0.0031 (14) | 0.0005 (12) | 0.0018 (15) |
C10 | 0.0331 (14) | 0.0375 (14) | 0.0382 (13) | −0.0027 (11) | −0.0006 (11) | −0.0020 (11) |
C11 | 0.052 (2) | 0.0538 (16) | 0.0549 (15) | −0.0053 (17) | 0.0077 (16) | −0.0043 (13) |
C12 | 0.058 (2) | 0.0512 (17) | 0.090 (2) | −0.008 (2) | 0.009 (2) | −0.0167 (16) |
C13 | 0.0519 (18) | 0.0401 (15) | 0.113 (3) | −0.001 (2) | 0.007 (2) | 0.0007 (16) |
C14 | 0.0363 (16) | 0.0584 (18) | 0.0803 (19) | 0.0010 (19) | −0.0009 (18) | 0.0230 (15) |
C15 | 0.0232 (11) | 0.0463 (14) | 0.0574 (14) | 0.0021 (16) | 0.0056 (16) | 0.0111 (11) |
C16 | 0.0206 (11) | 0.0627 (15) | 0.0433 (12) | 0.0054 (17) | 0.0015 (14) | 0.0114 (11) |
C17 | 0.0384 (15) | 0.086 (2) | 0.0478 (14) | 0.004 (2) | 0.0042 (16) | 0.0209 (14) |
C18 | 0.0448 (17) | 0.133 (3) | 0.0355 (13) | 0.007 (3) | 0.0048 (16) | 0.0119 (17) |
C19 | 0.049 (2) | 0.109 (3) | 0.0435 (15) | 0.004 (2) | 0.0008 (17) | −0.0165 (16) |
C20 | 0.049 (2) | 0.0719 (18) | 0.0436 (14) | 0.0053 (17) | −0.0027 (14) | −0.0088 (13) |
Mn1—O1 | 2.065 (2) | C5—C6 | 1.391 (4) |
Mn1—O5i | 2.181 (2) | C5—H5 | 0.93 |
Mn1—O1W | 2.190 (2) | C6—C7 | 1.398 (3) |
Mn1—N2 | 2.2384 (18) | C6—H6 | 0.93 |
Mn1—N1 | 2.258 (2) | C7—C8 | 1.390 (4) |
Mn1—O4i | 2.377 (2) | C7—C10 | 1.487 (3) |
Mn1—C10i | 2.619 (2) | C8—C9 | 1.368 (4) |
O1—C1 | 1.243 (3) | C8—H8 | 0.93 |
O2—C1 | 1.234 (4) | C9—H9 | 0.93 |
O3—C4 | 1.368 (3) | C10—Mn1ii | 2.619 (2) |
O3—C3 | 1.435 (3) | C11—C12 | 1.369 (4) |
O4—C10 | 1.263 (3) | C11—H11 | 0.93 |
O5—C10 | 1.260 (3) | C12—C13 | 1.365 (5) |
O1W—H1W1 | 0.85 (1) | C12—H12 | 0.93 |
O1W—H1W2 | 0.86 (1) | C13—C14 | 1.384 (5) |
N1—C11 | 1.345 (3) | C13—H13 | 0.93 |
N1—C15 | 1.349 (3) | C14—C15 | 1.384 (4) |
N2—C16 | 1.343 (3) | C14—H14 | 0.93 |
N2—C20 | 1.343 (3) | C15—C16 | 1.488 (4) |
C1—C2 | 1.523 (4) | C16—C17 | 1.386 (3) |
C2—C3 | 1.514 (4) | C17—C18 | 1.375 (5) |
C2—H2A | 0.97 | C17—H17 | 0.93 |
C2—H2B | 0.97 | C18—C19 | 1.378 (5) |
C3—H3A | 0.97 | C18—H18 | 0.93 |
C3—H3B | 0.97 | C19—C20 | 1.374 (4) |
C4—C5 | 1.369 (4) | C19—H19 | 0.93 |
C4—C9 | 1.382 (4) | C20—H20 | 0.93 |
O1—Mn1—O5i | 97.72 (9) | C4—C5—C6 | 119.0 (3) |
O1—Mn1—O1W | 87.71 (9) | C4—C5—H5 | 120.5 |
O5i—Mn1—O1W | 107.15 (8) | C6—C5—H5 | 120.5 |
O1—Mn1—N2 | 93.46 (9) | C5—C6—C7 | 121.4 (3) |
O5i—Mn1—N2 | 158.00 (8) | C5—C6—H6 | 119.3 |
O1W—Mn1—N2 | 92.12 (9) | C7—C6—H6 | 119.3 |
O1—Mn1—N1 | 163.82 (9) | C8—C7—C6 | 117.5 (3) |
O5i—Mn1—N1 | 92.57 (8) | C8—C7—C10 | 121.1 (3) |
O1W—Mn1—N1 | 101.18 (9) | C6—C7—C10 | 121.4 (3) |
N2—Mn1—N1 | 72.91 (8) | C9—C8—C7 | 121.4 (3) |
O1—Mn1—O4i | 86.31 (8) | C9—C8—H8 | 119.3 |
O5i—Mn1—O4i | 57.36 (6) | C7—C8—H8 | 119.3 |
O1W—Mn1—O4i | 162.32 (7) | C8—C9—C4 | 120.0 (3) |
N2—Mn1—O4i | 104.83 (7) | C8—C9—H9 | 120.0 |
N1—Mn1—O4i | 88.80 (8) | C4—C9—H9 | 120.0 |
O1—Mn1—C10i | 91.29 (9) | O5—C10—O4 | 120.8 (2) |
O5i—Mn1—C10i | 28.63 (7) | O5—C10—C7 | 119.4 (2) |
O1W—Mn1—C10i | 135.01 (8) | O4—C10—C7 | 119.7 (2) |
N2—Mn1—C10i | 132.79 (8) | O5—C10—Mn1ii | 56.02 (12) |
N1—Mn1—C10i | 91.82 (8) | O4—C10—Mn1ii | 64.93 (12) |
O4i—Mn1—C10i | 28.76 (6) | C7—C10—Mn1ii | 174.76 (19) |
C1—O1—Mn1 | 133.8 (2) | N1—C11—C12 | 123.3 (3) |
C4—O3—C3 | 119.1 (2) | N1—C11—H11 | 118.4 |
C10—O4—Mn1ii | 86.31 (14) | C12—C11—H11 | 118.4 |
C10—O5—Mn1ii | 95.35 (15) | C11—C12—C13 | 118.3 (3) |
Mn1—O1W—H1W1 | 141 (2) | C11—C12—H12 | 120.9 |
Mn1—O1W—H1W2 | 100 (4) | C13—C12—H12 | 120.9 |
H1W1—O1W—H1W2 | 105 (5) | C12—C13—C14 | 119.9 (3) |
C11—N1—C15 | 118.4 (2) | C12—C13—H13 | 120.1 |
C11—N1—Mn1 | 124.11 (18) | C14—C13—H13 | 120.1 |
C15—N1—Mn1 | 116.90 (16) | C13—C14—C15 | 119.1 (3) |
C16—N2—C20 | 119.3 (2) | C13—C14—H14 | 120.5 |
C16—N2—Mn1 | 117.68 (15) | C15—C14—H14 | 120.5 |
C20—N2—Mn1 | 122.65 (19) | N1—C15—C14 | 121.1 (2) |
O2—C1—O1 | 125.0 (3) | N1—C15—C16 | 115.7 (2) |
O2—C1—C2 | 119.3 (3) | C14—C15—C16 | 123.1 (2) |
O1—C1—C2 | 115.7 (3) | N2—C16—C17 | 121.1 (2) |
C3—C2—C1 | 113.7 (2) | N2—C16—C15 | 116.09 (19) |
C3—C2—H2A | 108.8 | C17—C16—C15 | 122.8 (2) |
C1—C2—H2A | 108.8 | C18—C17—C16 | 118.9 (3) |
C3—C2—H2B | 108.8 | C18—C17—H17 | 120.6 |
C1—C2—H2B | 108.8 | C16—C17—H17 | 120.6 |
H2A—C2—H2B | 107.7 | C17—C18—C19 | 120.3 (3) |
O3—C3—C2 | 105.4 (2) | C17—C18—H18 | 119.8 |
O3—C3—H3A | 110.7 | C19—C18—H18 | 119.8 |
C2—C3—H3A | 110.7 | C20—C19—C18 | 117.9 (3) |
O3—C3—H3B | 110.7 | C20—C19—H19 | 121.0 |
C2—C3—H3B | 110.7 | C18—C19—H19 | 121.0 |
H3A—C3—H3B | 108.8 | N2—C20—C19 | 122.5 (3) |
C5—C4—O3 | 125.3 (3) | N2—C20—H20 | 118.7 |
C5—C4—C9 | 120.7 (3) | C19—C20—H20 | 118.7 |
O3—C4—C9 | 114.0 (3) | ||
O5i—Mn1—O1—C1 | 88.7 (3) | C5—C6—C7—C8 | 0.8 (5) |
O1W—Mn1—O1—C1 | −18.3 (3) | C5—C6—C7—C10 | −176.9 (3) |
N2—Mn1—O1—C1 | −110.3 (3) | C6—C7—C8—C9 | −0.1 (6) |
N1—Mn1—O1—C1 | −142.3 (3) | C10—C7—C8—C9 | 177.6 (3) |
O4i—Mn1—O1—C1 | 145.1 (3) | C7—C8—C9—C4 | −0.7 (6) |
C10i—Mn1—O1—C1 | 116.7 (3) | C5—C4—C9—C8 | 0.7 (5) |
O1—Mn1—N1—C11 | −141.2 (3) | O3—C4—C9—C8 | −179.3 (3) |
O5i—Mn1—N1—C11 | −11.6 (3) | Mn1ii—O5—C10—O4 | 4.0 (3) |
O1W—Mn1—N1—C11 | 96.4 (3) | Mn1ii—O5—C10—C7 | −176.9 (2) |
N2—Mn1—N1—C11 | −174.8 (3) | Mn1ii—O4—C10—O5 | −3.7 (3) |
O4i—Mn1—N1—C11 | −68.9 (3) | Mn1ii—O4—C10—C7 | 177.2 (2) |
C10i—Mn1—N1—C11 | −40.3 (3) | C8—C7—C10—O5 | −177.9 (3) |
O1—Mn1—N1—C15 | 29.6 (5) | C6—C7—C10—O5 | −0.3 (4) |
O5i—Mn1—N1—C15 | 159.2 (2) | C8—C7—C10—O4 | 1.2 (5) |
O1W—Mn1—N1—C15 | −92.7 (2) | C6—C7—C10—O4 | 178.8 (3) |
N2—Mn1—N1—C15 | −3.9 (2) | C15—N1—C11—C12 | 0.1 (5) |
O4i—Mn1—N1—C15 | 102.0 (2) | Mn1—N1—C11—C12 | 170.9 (3) |
C10i—Mn1—N1—C15 | 130.6 (2) | N1—C11—C12—C13 | −0.6 (6) |
O1—Mn1—N2—C16 | −172.6 (2) | C11—C12—C13—C14 | 1.0 (6) |
O5i—Mn1—N2—C16 | −52.0 (4) | C12—C13—C14—C15 | −0.8 (6) |
O1W—Mn1—N2—C16 | 99.5 (2) | C11—N1—C15—C14 | 0.1 (5) |
N1—Mn1—N2—C16 | −1.5 (2) | Mn1—N1—C15—C14 | −171.3 (3) |
O4i—Mn1—N2—C16 | −85.5 (2) | C11—N1—C15—C16 | 179.8 (3) |
C10i—Mn1—N2—C16 | −77.7 (2) | Mn1—N1—C15—C16 | 8.3 (4) |
O1—Mn1—N2—C20 | 14.6 (2) | C13—C14—C15—N1 | 0.3 (5) |
O5i—Mn1—N2—C20 | 135.2 (2) | C13—C14—C15—C16 | −179.4 (3) |
O1W—Mn1—N2—C20 | −73.2 (2) | C20—N2—C16—C17 | 0.1 (5) |
N1—Mn1—N2—C20 | −174.3 (3) | Mn1—N2—C16—C17 | −172.9 (2) |
O4i—Mn1—N2—C20 | 101.7 (2) | C20—N2—C16—C15 | 179.2 (3) |
C10i—Mn1—N2—C20 | 109.6 (2) | Mn1—N2—C16—C15 | 6.2 (4) |
Mn1—O1—C1—O2 | 10.1 (5) | N1—C15—C16—N2 | −9.7 (4) |
Mn1—O1—C1—C2 | −170.1 (2) | C14—C15—C16—N2 | 170.0 (3) |
O2—C1—C2—C3 | 151.1 (3) | N1—C15—C16—C17 | 169.4 (3) |
O1—C1—C2—C3 | −28.7 (3) | C14—C15—C16—C17 | −10.9 (5) |
C4—O3—C3—C2 | 179.2 (2) | N2—C16—C17—C18 | −0.1 (5) |
C1—C2—C3—O3 | −67.6 (3) | C15—C16—C17—C18 | −179.1 (3) |
C3—O3—C4—C5 | −5.4 (5) | C16—C17—C18—C19 | 0.1 (6) |
C3—O3—C4—C9 | 174.7 (3) | C17—C18—C19—C20 | −0.2 (6) |
O3—C4—C5—C6 | 180.0 (3) | C16—N2—C20—C19 | −0.3 (5) |
C9—C4—C5—C6 | −0.1 (5) | Mn1—N2—C20—C19 | 172.4 (2) |
C4—C5—C6—C7 | −0.7 (5) | C18—C19—C20—N2 | 0.3 (5) |
Symmetry codes: (i) −x+5/2, −y+1, z−1/2; (ii) −x+5/2, −y+1, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W2···O2 | 0.86 (1) | 1.82 (2) | 2.658 (3) | 164 (6) |
O1W—H1W1···O4iii | 0.85 (1) | 1.96 (1) | 2.797 (3) | 170 (3) |
Symmetry code: (iii) −x+3/2, −y+1, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | [Mn(C10H8N2)(C10H8O5)(H2O)] |
Mr | 437.30 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 295 |
a, b, c (Å) | 6.7770 (3), 16.2626 (6), 17.3730 (5) |
V (Å3) | 1914.71 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.73 |
Crystal size (mm) | 0.35 × 0.29 × 0.18 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.624, 0.880 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18852, 4362, 3057 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.089, 0.95 |
No. of reflections | 4362 |
No. of parameters | 264 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.34, −0.30 |
Absolute structure | Flack (1983), with 1860 Friedel pairs |
Absolute structure parameter | 0.36 (2) |
Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001) and OLEX (Dolomanov et al., 2003), publCIF (Westrip, 2007).
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W2···O2 | 0.86 (1) | 1.82 (2) | 2.658 (3) | 164 (6) |
O1W—H1W1···O4i | 0.85 (1) | 1.96 (1) | 2.797 (3) | 170 (3) |
Symmetry code: (i) −x+3/2, −y+1, z−1/2. |