Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055717/rt2011sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055717/rt2011Isup2.hkl |
CCDC reference: 641729
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.033
- wR factor = 0.102
- Data-to-parameter ratio = 11.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 6 PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.80 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Mn1 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.12 PLAT350_ALERT_3_C Short C-H Bond (0.96A) C3 - H5A ... 0.84 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 8 PLAT745_ALERT_1_C D-H Calc 0.842(2), Rep 0.84000 ...... Missing su O3 -H3A 1.555 1.555 PLAT745_ALERT_1_C D-H Calc 0.872(3), Rep 0.87000 ...... Missing su O4 -H4A 1.555 1.555 PLAT746_ALERT_1_C H...A Calc 1.709(2), Rep 1.71000 ...... Missing su H3A -O6 1.555 1.555 PLAT746_ALERT_1_C H...A Calc 1.725(2), Rep 1.73000 ...... Missing su H4A -O2 1.555 1.555 PLAT748_ALERT_1_C D-H..A Calc 160.7(3), Rep 161.00 ...... Missing su O3 -H3A -O6 1.555 1.555 1.555 PLAT748_ALERT_1_C D-H..A Calc 150.1(4), Rep 150.00 ...... Missing su O4 -H4A -O2 1.555 1.555 1.555
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 16
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Riordan & Blair (1979); Klotz (2005); Tang, Tan & Cao (2007); Tang, Tan, Chen & Cao (2007); Tang, Yang et al. (2007).
MnCl2 was acquired from Aldrich, and 3,3-azo-bis(6-hydroxybenzoic acid) was synthesized according to the literature (Riordan & Blair, 1979). To a solution of 3,3-azo-bis(6-hydroxybenzoic acid) (301 mg, 1 mmol) in water (60 ml) and sodium hydroxide (1 M, 2 ml), MnCl2 (349 mg, 1 mmol) was added. The mixture was stirred at 373 K for 12 h and then filtered. Single-crystals were grown from the filtrate after six weeks (Tang et al., 2007), then moved to a box with UV light (365 nm)- illumination in room temperature. The orange crystals turned to deep red crystals about two weeks later. We collected and separated them carefully, then dried in a desiccator. The yield reaches 92 percent based on the orange crystals. Compound (I) is stable in air and insoluble in water.
The hydroxy and C-bound H atoms were placed in calculated postions (C—H = 0.93 Å, O—H = 0.82 Å) and included in the refinement in the riding-model approximation, with Uiso(H) = 1.2Ueq(C,O). The water H atoms were located in a difference Fourier map and isotropically refined with distance restraints of O—H = 0.85 (1) Å and H···H = 1.39 (1) Å.
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXL97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).
[Mn(C14H8N2O6)(H2O)4] | F(000) = 876 |
Mr = 427.23 | Dx = 1.660 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 935 reflections |
a = 9.486 (2) Å | θ = 2.2–26° |
b = 11.490 (3) Å | µ = 0.83 mm−1 |
c = 16.322 (4) Å | T = 293 K |
β = 106.076 (3)° | Block, red |
V = 1709.4 (7) Å3 | 0.31 × 0.23 × 0.21 mm |
Z = 4 |
Bruker SMART APEX CCD area-detector diffractometer | 3341 independent reflections |
Radiation source: fine-focus sealed tube | 2933 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
ϕ and ω scans | θmax = 26.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −11→11 |
Tmin = 0.80, Tmax = 0.84 | k = −13→14 |
8959 measured reflections | l = −20→19 |
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)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.102 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.55 | w = 1/[σ2(Fo2) + (0.0368P)2] where P = (Fo2 + 2Fc2)/3 |
3341 reflections | (Δ/σ)max = 0.001 |
284 parameters | Δρmax = 0.34 e Å−3 |
16 restraints | Δρmin = −0.37 e Å−3 |
[Mn(C14H8N2O6)(H2O)4] | V = 1709.4 (7) Å3 |
Mr = 427.23 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.486 (2) Å | µ = 0.83 mm−1 |
b = 11.490 (3) Å | T = 293 K |
c = 16.322 (4) Å | 0.31 × 0.23 × 0.21 mm |
β = 106.076 (3)° |
Bruker SMART APEX CCD area-detector diffractometer | 3341 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 2933 reflections with I > 2σ(I) |
Tmin = 0.80, Tmax = 0.84 | Rint = 0.019 |
8959 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | 16 restraints |
wR(F2) = 0.102 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.55 | Δρmax = 0.34 e Å−3 |
3341 reflections | Δρmin = −0.37 e Å−3 |
284 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Mn1 | 0.71229 (3) | 0.36073 (2) | 0.210538 (18) | 0.03035 (13) | |
O4W | 0.84712 (17) | 0.45769 (13) | 0.31718 (7) | 0.0454 (4) | |
O6 | 0.57181 (16) | 0.26262 (12) | 0.10622 (9) | 0.0378 (3) | |
N2 | 0.09166 (19) | −0.14057 (13) | 0.00328 (11) | 0.0331 (4) | |
O5 | 0.4699 (2) | 0.13827 (14) | 0.17648 (10) | 0.0518 (5) | |
O4 | −0.30717 (19) | −0.50644 (14) | −0.04431 (10) | 0.0503 (4) | |
N1 | 0.12243 (19) | −0.10512 (15) | −0.06254 (10) | 0.0311 (4) | |
C14 | 0.4863 (2) | 0.17786 (17) | 0.10958 (12) | 0.0322 (4) | |
O3 | 0.5107 (2) | 0.25868 (15) | −0.05407 (10) | 0.0563 (5) | |
O3W | 0.88504 (19) | 0.23991 (14) | 0.21347 (7) | 0.0525 (4) | |
O2W | 0.6512 (2) | 0.25207 (16) | 0.30695 (10) | 0.0540 (4) | |
C13 | 0.3039 (2) | 0.03679 (17) | 0.02394 (13) | 0.0299 (4) | |
C12 | −0.1180 (2) | −0.39112 (18) | 0.04972 (13) | 0.0333 (4) | |
C11 | 0.4008 (2) | 0.12786 (16) | 0.02602 (13) | 0.0292 (4) | |
C10 | −0.0114 (2) | −0.23392 (16) | −0.01245 (12) | 0.0310 (4) | |
C9 | −0.2083 (2) | −0.41852 (17) | −0.03162 (13) | 0.0345 (4) | |
C8 | −0.1046 (2) | −0.26171 (19) | −0.09284 (13) | 0.0372 (5) | |
O1W | 0.5321 (2) | 0.47858 (14) | 0.20352 (11) | 0.0637 (5) | |
C7 | 0.2227 (2) | −0.01053 (16) | −0.05305 (12) | 0.0309 (4) | |
C6 | −0.0207 (2) | −0.29866 (18) | 0.05741 (12) | 0.0362 (5) | |
C5 | 0.4158 (2) | 0.17191 (19) | −0.05163 (13) | 0.0369 (5) | |
C3 | −0.2000 (3) | −0.35306 (19) | −0.10170 (15) | 0.0411 (5) | |
C2 | 0.2400 (3) | 0.0341 (2) | −0.12885 (14) | 0.0412 (5) | |
C1 | 0.3339 (3) | 0.1242 (2) | −0.12874 (14) | 0.0470 (6) | |
C4 | −0.1291 (3) | −0.45639 (19) | 0.12689 (14) | 0.0422 (5) | |
O2 | −0.22138 (18) | −0.53993 (13) | 0.11428 (10) | 0.0474 (4) | |
O1 | −0.0512 (2) | −0.42829 (17) | 0.19838 (10) | 0.0677 (6) | |
H13A | 0.301 (2) | 0.0110 (17) | 0.0730 (14) | 0.030 (5)* | |
H8A | −0.111 (3) | −0.2182 (17) | −0.1412 (15) | 0.036 (6)* | |
H1A | 0.336 (3) | 0.165 (2) | −0.1854 (17) | 0.047 (6)* | |
H2A | 0.178 (4) | 0.012 (3) | −0.178 (2) | 0.079 (10)* | |
H5A | −0.261 (3) | −0.3663 (18) | −0.1493 (18) | 0.042 (7)* | |
H6A | 0.0455 (7) | −0.2856 (8) | 0.11412 (19) | 0.062 (8)* | |
H2WB | 0.6323 | 0.2541 | 0.3549 | 0.055 (8)* | |
H4WB | 0.9093 | 0.4932 | 0.2975 | 0.074 (10)* | |
H3A | 0.5395 (5) | 0.2747 (2) | −0.00175 (8) | 0.058 (8)* | |
H4WA | 0.8832 | 0.4458 | 0.3703 | 0.085 (11)* | |
H3WB | 0.8753 | 0.2116 | 0.1641 | 0.098 (12)* | |
H1WB | 0.5363 | 0.5277 | 0.2431 | 0.075 (10)* | |
H3WA | 0.9322 | 0.1924 | 0.2511 | 0.097 (12)* | |
H4A | −0.2990 (4) | −0.5379 (3) | 0.00539 (10) | 0.061 (8)* | |
H1WA | 0.4804 | 0.5058 | 0.1563 | 0.086 (11)* | |
H2WA | 0.5834 | 0.2157 | 0.2710 | 0.114 (14)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Mn1 | 0.0338 (2) | 0.03079 (19) | 0.02409 (19) | −0.00292 (12) | 0.00414 (13) | −0.00169 (11) |
O4W | 0.0477 (9) | 0.0535 (9) | 0.0323 (8) | −0.0134 (8) | 0.0067 (7) | −0.0077 (7) |
O6 | 0.0439 (8) | 0.0385 (8) | 0.0290 (7) | −0.0167 (7) | 0.0068 (6) | −0.0067 (6) |
N2 | 0.0363 (10) | 0.0348 (9) | 0.0263 (9) | −0.0097 (7) | 0.0055 (7) | 0.0003 (7) |
O5 | 0.0692 (12) | 0.0565 (10) | 0.0254 (8) | −0.0264 (8) | 0.0061 (8) | 0.0029 (7) |
O4 | 0.0569 (10) | 0.0485 (9) | 0.0370 (9) | −0.0288 (8) | −0.0014 (7) | 0.0031 (7) |
N1 | 0.0334 (9) | 0.0325 (8) | 0.0268 (8) | −0.0077 (7) | 0.0071 (7) | −0.0021 (7) |
C14 | 0.0342 (11) | 0.0320 (10) | 0.0296 (10) | −0.0048 (8) | 0.0077 (8) | −0.0014 (8) |
O3 | 0.0746 (12) | 0.0654 (10) | 0.0304 (8) | −0.0439 (9) | 0.0168 (8) | −0.0058 (7) |
O3W | 0.0617 (11) | 0.0620 (10) | 0.0317 (8) | 0.0259 (9) | 0.0098 (7) | −0.0018 (8) |
O2W | 0.0654 (11) | 0.0650 (10) | 0.0335 (9) | −0.0240 (9) | 0.0169 (8) | −0.0025 (8) |
C13 | 0.0340 (11) | 0.0304 (10) | 0.0257 (10) | −0.0044 (8) | 0.0090 (8) | −0.0002 (8) |
C12 | 0.0350 (11) | 0.0325 (10) | 0.0298 (11) | −0.0088 (8) | 0.0047 (8) | 0.0017 (8) |
C11 | 0.0301 (10) | 0.0316 (10) | 0.0255 (10) | −0.0039 (8) | 0.0069 (8) | −0.0021 (8) |
C10 | 0.0328 (10) | 0.0314 (9) | 0.0286 (10) | −0.0076 (8) | 0.0078 (8) | −0.0003 (8) |
C9 | 0.0342 (11) | 0.0334 (10) | 0.0335 (11) | −0.0099 (9) | 0.0052 (9) | −0.0013 (8) |
C8 | 0.0374 (11) | 0.0445 (12) | 0.0273 (10) | −0.0089 (9) | 0.0051 (9) | 0.0056 (9) |
O1W | 0.0627 (12) | 0.0665 (11) | 0.0470 (10) | 0.0277 (10) | −0.0096 (9) | −0.0223 (9) |
C7 | 0.0291 (10) | 0.0322 (10) | 0.0305 (10) | −0.0072 (8) | 0.0068 (8) | −0.0027 (8) |
C6 | 0.0403 (11) | 0.0402 (11) | 0.0240 (10) | −0.0123 (9) | 0.0020 (8) | 0.0015 (8) |
C5 | 0.0421 (12) | 0.0397 (11) | 0.0304 (11) | −0.0144 (9) | 0.0123 (9) | −0.0021 (9) |
C3 | 0.0440 (13) | 0.0483 (13) | 0.0245 (10) | −0.0154 (10) | −0.0014 (10) | −0.0002 (9) |
C2 | 0.0463 (13) | 0.0512 (13) | 0.0243 (10) | −0.0171 (11) | 0.0069 (9) | −0.0051 (9) |
C1 | 0.0579 (15) | 0.0576 (14) | 0.0259 (11) | −0.0252 (12) | 0.0126 (10) | −0.0005 (10) |
C4 | 0.0463 (13) | 0.0428 (12) | 0.0334 (11) | −0.0167 (10) | 0.0044 (10) | 0.0040 (9) |
O2 | 0.0531 (10) | 0.0464 (9) | 0.0375 (8) | −0.0238 (8) | 0.0039 (7) | 0.0087 (7) |
O1 | 0.0855 (14) | 0.0753 (12) | 0.0312 (9) | −0.0476 (11) | −0.0025 (9) | 0.0096 (8) |
Mn1—O3W | 2.1380 (15) | C13—C7 | 1.390 (3) |
Mn1—O1W | 2.1588 (16) | C13—H13A | 0.86 (2) |
Mn1—O4W | 2.1619 (14) | C12—C6 | 1.390 (3) |
Mn1—O6 | 2.1654 (14) | C12—C9 | 1.402 (3) |
Mn1—O2i | 2.1713 (15) | C12—C4 | 1.495 (3) |
Mn1—O2W | 2.2083 (15) | C11—C5 | 1.408 (3) |
O4W—H4WB | 0.8501 | C10—C6 | 1.384 (3) |
O4W—H4WA | 0.8500 | C10—C8 | 1.401 (3) |
O6—C14 | 1.278 (2) | C9—C3 | 1.389 (3) |
N2—N1 | 1.256 (2) | C8—C3 | 1.367 (3) |
N2—C10 | 1.426 (2) | C8—H8A | 0.92 (2) |
O5—C14 | 1.232 (3) | O1W—H1WB | 0.8501 |
O4—C9 | 1.355 (2) | O1W—H1WA | 0.8500 |
O4—H4A | 0.872 (3) | C7—C2 | 1.391 (3) |
N1—C7 | 1.424 (2) | C6—H6A | 0.975 (4) |
C14—C11 | 1.495 (3) | C5—C1 | 1.395 (3) |
O3—C5 | 1.351 (2) | C3—H5A | 0.84 (3) |
O3—H3A | 0.8418 (19) | C2—C1 | 1.365 (3) |
O3W—H3WB | 0.8502 | C2—H2A | 0.90 (3) |
O3W—H3WA | 0.8502 | C1—H1A | 1.04 (3) |
O2W—H2WB | 0.8501 | C4—O1 | 1.239 (3) |
O2W—H2WA | 0.8500 | C4—O2 | 1.277 (2) |
C13—C11 | 1.387 (3) | O2—Mn1ii | 2.1713 (15) |
O3W—Mn1—O1W | 177.68 (6) | C13—C11—C5 | 118.74 (18) |
O3W—Mn1—O4W | 92.16 (6) | C13—C11—C14 | 120.05 (17) |
O1W—Mn1—O4W | 90.15 (6) | C5—C11—C14 | 121.21 (17) |
O3W—Mn1—O6 | 88.88 (6) | C6—C10—C8 | 118.78 (17) |
O1W—Mn1—O6 | 88.80 (6) | C6—C10—N2 | 116.91 (17) |
O4W—Mn1—O6 | 178.02 (5) | C8—C10—N2 | 124.29 (17) |
O3W—Mn1—O2i | 89.06 (7) | O4—C9—C3 | 118.19 (18) |
O1W—Mn1—O2i | 90.90 (8) | O4—C9—C12 | 121.86 (18) |
O4W—Mn1—O2i | 94.95 (6) | C3—C9—C12 | 119.94 (18) |
O6—Mn1—O2i | 86.75 (6) | C3—C8—C10 | 120.11 (19) |
O3W—Mn1—O2W | 88.16 (7) | C3—C8—H8A | 116.1 (14) |
O1W—Mn1—O2W | 91.84 (8) | C10—C8—H8A | 123.6 (14) |
O4W—Mn1—O2W | 86.06 (6) | Mn1—O1W—H1WB | 120.4 |
O6—Mn1—O2W | 92.30 (6) | Mn1—O1W—H1WA | 121.9 |
O2i—Mn1—O2W | 177.08 (7) | H1WB—O1W—H1WA | 109.7 |
Mn1—O4W—H4WB | 105.1 | C13—C7—C2 | 119.17 (18) |
Mn1—O4W—H4WA | 136.0 | C13—C7—N1 | 125.68 (17) |
H4WB—O4W—H4WA | 109.7 | C2—C7—N1 | 115.13 (17) |
C14—O6—Mn1 | 128.50 (12) | C10—C6—C12 | 121.88 (18) |
N1—N2—C10 | 113.58 (15) | C10—C6—H6A | 121.9 (3) |
C9—O4—H4A | 106.7 (2) | C12—C6—H6A | 116.1 (3) |
N2—N1—C7 | 117.43 (15) | O3—C5—C1 | 118.21 (18) |
O5—C14—O6 | 123.82 (18) | O3—C5—C11 | 121.75 (18) |
O5—C14—C11 | 119.81 (17) | C1—C5—C11 | 120.03 (18) |
O6—C14—C11 | 116.36 (16) | C8—C3—C9 | 121.0 (2) |
C5—O3—H3A | 99.4 (4) | C8—C3—H5A | 120.1 (16) |
Mn1—O3W—H3WB | 110.2 | C9—C3—H5A | 118.6 (16) |
Mn1—O3W—H3WA | 132.8 | C1—C2—C7 | 121.1 (2) |
H3WB—O3W—H3WA | 109.6 | C1—C2—H2A | 119 (2) |
Mn1—O2W—H2WB | 143.5 | C7—C2—H2A | 119 (2) |
Mn1—O2W—H2WA | 94.8 | C2—C1—C5 | 120.0 (2) |
H2WB—O2W—H2WA | 109.7 | C2—C1—H1A | 120.7 (14) |
C11—C13—C7 | 121.00 (18) | C5—C1—H1A | 118.9 (14) |
C11—C13—H13A | 115.6 (14) | O1—C4—O2 | 123.5 (2) |
C7—C13—H13A | 123.4 (14) | O1—C4—C12 | 120.01 (19) |
C6—C12—C9 | 118.27 (18) | O2—C4—C12 | 116.53 (18) |
C6—C12—C4 | 120.50 (18) | C4—O2—Mn1ii | 126.99 (14) |
C9—C12—C4 | 121.20 (18) |
Symmetry codes: (i) x+1, y+1, z; (ii) x−1, y−1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4W—H4WB···O1i | 0.85 | 1.98 | 2.728 (2) | 147 |
O4W—H4WA···N2iii | 0.85 | 2.24 | 3.043 (2) | 157 |
O3—H3A···O6 | 0.84 | 1.71 | 2.519 (2) | 161 |
O3W—H3WB···N1iv | 0.85 | 2.07 | 2.894 (2) | 165 |
O4—H4A···O2 | 0.87 | 1.73 | 2.519 (2) | 150 |
O1W—H1WB···O5iii | 0.85 | 1.84 | 2.688 (2) | 175 |
O3W—H3WA···O1iii | 0.85 | 1.83 | 2.652 (3) | 161 |
O1W—H1WA···O4v | 0.85 | 2.09 | 2.887 (3) | 155 |
O2W—H2WA···O5 | 0.85 | 1.85 | 2.678 (2) | 165 |
Symmetry codes: (i) x+1, y+1, z; (iii) −x+1, y+1/2, −z+1/2; (iv) −x+1, −y, −z; (v) −x, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | [Mn(C14H8N2O6)(H2O)4] |
Mr | 427.23 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 9.486 (2), 11.490 (3), 16.322 (4) |
β (°) | 106.076 (3) |
V (Å3) | 1709.4 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.83 |
Crystal size (mm) | 0.31 × 0.23 × 0.21 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.80, 0.84 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8959, 3341, 2933 |
Rint | 0.019 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.102, 1.55 |
No. of reflections | 3341 |
No. of parameters | 284 |
No. of restraints | 16 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.34, −0.37 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000).
Mn1—O3W | 2.1380 (15) | Mn1—O6 | 2.1654 (14) |
Mn1—O1W | 2.1588 (16) | Mn1—O2i | 2.1713 (15) |
Mn1—O4W | 2.1619 (14) | Mn1—O2W | 2.2083 (15) |
O3W—Mn1—O1W | 177.68 (6) | O4W—Mn1—O2i | 94.95 (6) |
O3W—Mn1—O4W | 92.16 (6) | O6—Mn1—O2i | 86.75 (6) |
O1W—Mn1—O4W | 90.15 (6) | O3W—Mn1—O2W | 88.16 (7) |
O3W—Mn1—O6 | 88.88 (6) | O1W—Mn1—O2W | 91.84 (8) |
O1W—Mn1—O6 | 88.80 (6) | O4W—Mn1—O2W | 86.06 (6) |
O4W—Mn1—O6 | 178.02 (5) | O6—Mn1—O2W | 92.30 (6) |
O3W—Mn1—O2i | 89.06 (7) | O2i—Mn1—O2W | 177.08 (7) |
O1W—Mn1—O2i | 90.90 (8) |
Symmetry code: (i) x+1, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4W—H4WB···O1i | 0.85 | 1.98 | 2.728 (2) | 147 |
O4W—H4WA···N2ii | 0.85 | 2.24 | 3.043 (2) | 157 |
O3—H3A···O6 | 0.84 | 1.71 | 2.519 (2) | 161 |
O3W—H3WB···N1iii | 0.85 | 2.07 | 2.894 (2) | 165 |
O4—H4A···O2 | 0.87 | 1.73 | 2.519 (2) | 150 |
O1W—H1WB···O5ii | 0.85 | 1.84 | 2.688 (2) | 175 |
O3W—H3WA···O1ii | 0.85 | 1.83 | 2.652 (3) | 161 |
O1W—H1WA···O4iv | 0.85 | 2.09 | 2.887 (3) | 155 |
O2W—H2WA···O5 | 0.85 | 1.85 | 2.678 (2) | 165 |
Symmetry codes: (i) x+1, y+1, z; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+1, −y, −z; (iv) −x, −y, −z. |
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Olsalazine - 3,3-azo-bis(6-hydroxybenzoic acid) - has been widely used to prevent and treat the inflammatory bowel diseases, such as ulcerative colitis (Klotz, 2005). Recently, we have successfully synthesized a serial of Zn (Tang, Tan, Chen & Cao, 2007), Cd and Co (Tang, Yang et al., 2007) complexes with olsalazine as building block. Also, we have reported a Mn complex of olsalazine crystallized in chiral group P4(3)2(1)2 (Tang, Tan & Cao, 2007), however in the condition of UV light- illumination with wavenumber 365 nm, to our surprise, we found the colour of the crystals turn from orange to deep red after two weeks. The further investigation by X-ray single-crystal structure analysis revealed that the space group change from P4(3)2(1)2 to P2(1)/c. Here we reported the new crystal structure of the title compound, (I)- a new Manganese complex of olsalazine.
In (I) (Fig. 1), the Mn atom is hexacoordinated (Fig. 1) by two O atoms from two L ligands (H2L = 3,3-azo-bis(6-hydroxybenzoic acid)) and four water molecules in a distorted octahedral geometry (Table 1). Two ligands are cis to each other in an octahedral environment. Each ligand L acts as a carboxylate bridge, that leads to formation of polymeric chain running in the direction [110]. Two neighbouring polymeric chains are paired by π···π interactions between the aromatic rings - the distances Cg1···Cg1i and Cg2···Cg2i are 3.830 (16) and 4.476 (17) Å, respectively [Cg1 and Cg2 are centroids of C3/C8/C10/C6/C12/C9 and C1/C2/C7/C13/C11/C5 rings, respectively; symmetry code: (i) 1 - x,-y,- -z; (ii) -x,-1 - y,- -z]. The crystal packing is further stabilized by the intermolecular O—H···O and O—H···N hydrogen bonds (Table 2).