Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807067827/dn2293sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807067827/dn2293Isup2.hkl |
CCDC reference: 677390
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.007 Å
- R factor = 0.050
- wR factor = 0.133
- Data-to-parameter ratio = 13.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Co1 PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 8
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
All H atoms attached to C atoms and O(hydroxyl) atom were fixed geometrically and treated as riding with C—H = 0.93 Å and O—H = 0.86 Å with Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(O). H atoms of water molecule were located in difference Fourier maps and included in the subsequent refinement using restraints (O—H = 0.82 (1) Å and H···H = 1.34 (2) Å) with Uiso(H) = 1.5Ueq(O). In the last stage of refinement, the H atoms were treated as riding on their parent O atoms.
The crystal used was twinned with two domains in the ratio 0.076/0.924. The twin law is [1.00 0.00 0.00 0.00 - 1.00 0.00 - 1.00 0.00 - 1.00].
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
[Co(C14H8N2O6)(H2O)4] | F(000) = 884 |
Mr = 431.22 | Dx = 1.726 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 935 reflections |
a = 9.5152 (14) Å | θ = 2.2–26° |
b = 11.2452 (17) Å | µ = 1.10 mm−1 |
c = 16.194 (2) Å | T = 296 K |
β = 106.687 (2)° | Block, red |
V = 1659.8 (4) Å3 | 0.10 × 0.08 × 0.08 mm |
Z = 4 |
Bruker SMART APEX CCD area-detector diffractometer | 3427 independent reflections |
Radiation source: fine-focus sealed tube | 1976 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.062 |
ϕ and ω scans | θmax = 26.4°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −11→11 |
Tmin = 0.898, Tmax = 0.918 | k = −14→14 |
11094 measured reflections | l = −19→20 |
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)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.133 | w = 1/[σ2(Fo2) + (0.0717P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.94 | (Δ/σ)max = 0.001 |
3427 reflections | Δρmax = 0.50 e Å−3 |
246 parameters | Δρmin = −0.44 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0050 (11) |
[Co(C14H8N2O6)(H2O)4] | V = 1659.8 (4) Å3 |
Mr = 431.22 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.5152 (14) Å | µ = 1.10 mm−1 |
b = 11.2452 (17) Å | T = 296 K |
c = 16.194 (2) Å | 0.10 × 0.08 × 0.08 mm |
β = 106.687 (2)° |
Bruker SMART APEX CCD area-detector diffractometer | 3427 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 1976 reflections with I > 2σ(I) |
Tmin = 0.898, Tmax = 0.918 | Rint = 0.062 |
11094 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.133 | H-atom parameters constrained |
S = 0.94 | Δρmax = 0.50 e Å−3 |
3427 reflections | Δρmin = −0.44 e Å−3 |
246 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 | ||
Co1 | 0.71433 (7) | 0.14001 (5) | 0.21254 (4) | 0.0333 (2) | |
O1W | 0.8824 (4) | 0.2527 (3) | 0.2134 (2) | 0.0515 (9) | |
H1WA | 0.9251 | 0.3002 | 0.2506 | 0.077* | |
H1WB | 0.8799 | 0.2780 | 0.1654 | 0.077* | |
O2W | 0.6621 (4) | 0.2503 (3) | 0.3053 (2) | 0.0537 (10) | |
H2WA | 0.5912 | 0.2842 | 0.2726 | 0.080* | |
H2WB | 0.6352 | 0.2127 | 0.3415 | 0.080* | |
O3W | 0.5405 (4) | 0.0277 (3) | 0.2068 (2) | 0.0575 (10) | |
H3WA | 0.5494 | −0.0263 | 0.2418 | 0.086* | |
H3WB | 0.5144 | 0.0028 | 0.1579 | 0.086* | |
O4W | 0.8418 (4) | 0.0398 (3) | 0.31539 (19) | 0.0455 (9) | |
H4WA | 0.8933 | 0.0663 | 0.3610 | 0.068* | |
H4WB | 0.8900 | −0.0006 | 0.2912 | 0.068* | |
N2 | 0.0915 (4) | 0.6415 (3) | 0.0012 (2) | 0.0366 (9) | |
N1 | 0.1224 (4) | 0.6059 (3) | −0.0651 (2) | 0.0374 (10) | |
O1 | 0.5775 (4) | 0.2345 (3) | 0.10743 (19) | 0.0402 (8) | |
O2 | 0.4732 (4) | 0.3607 (3) | 0.1776 (2) | 0.0542 (10) | |
O3 | 0.5168 (4) | 0.2395 (3) | −0.0547 (2) | 0.0609 (11) | |
H3A | 0.5587 | 0.2174 | −0.0055 | 0.091* | |
O4 | −0.3150 (4) | 1.0087 (3) | −0.0450 (2) | 0.0533 (10) | |
H4A | −0.3126 | 1.0395 | 0.0012 | 0.080* | |
O5 | −0.2290 (4) | 1.0400 (3) | 0.1171 (2) | 0.0455 (9) | |
O6 | −0.0537 (4) | 0.9267 (3) | 0.2009 (2) | 0.0637 (12) | |
C1 | 0.4906 (5) | 0.3199 (4) | 0.1097 (3) | 0.0358 (11) | |
C2 | 0.4027 (5) | 0.3698 (4) | 0.0249 (3) | 0.0326 (10) | |
C3 | 0.4191 (6) | 0.3262 (4) | −0.0520 (3) | 0.0399 (12) | |
C4 | 0.3349 (6) | 0.3724 (4) | −0.1303 (3) | 0.0523 (15) | |
H4 | 0.3427 | 0.3408 | −0.1819 | 0.063* | |
C5 | 0.2420 (5) | 0.4632 (4) | −0.1309 (3) | 0.0441 (13) | |
H5 | 0.1885 | 0.4954 | −0.1835 | 0.053* | |
C6 | 0.2240 (5) | 0.5101 (4) | −0.0547 (3) | 0.0346 (11) | |
C7 | 0.3054 (5) | 0.4617 (4) | 0.0228 (3) | 0.0356 (11) | |
H7 | 0.2944 | 0.4914 | 0.0742 | 0.043* | |
C8 | −0.0120 (5) | 0.7371 (4) | −0.0142 (3) | 0.0348 (11) | |
C9 | −0.1058 (5) | 0.7662 (4) | −0.0956 (3) | 0.0414 (12) | |
H9 | −0.1024 | 0.7229 | −0.1439 | 0.050* | |
C10 | −0.2027 (6) | 0.8587 (4) | −0.1037 (3) | 0.0446 (12) | |
H10 | −0.2621 | 0.8798 | −0.1580 | 0.054* | |
C11 | −0.2134 (5) | 0.9212 (4) | −0.0320 (3) | 0.0386 (12) | |
C12 | −0.1231 (5) | 0.8923 (4) | 0.0500 (3) | 0.0351 (11) | |
C13 | −0.0236 (6) | 0.8005 (4) | 0.0566 (3) | 0.0419 (12) | |
H13 | 0.0377 | 0.7808 | 0.1108 | 0.050* | |
C14 | −0.1338 (5) | 0.9566 (4) | 0.1286 (3) | 0.0403 (12) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.0379 (4) | 0.0295 (3) | 0.0312 (3) | 0.0035 (3) | 0.0078 (3) | 0.0014 (3) |
O1W | 0.060 (2) | 0.055 (2) | 0.0364 (19) | −0.0171 (19) | 0.0088 (17) | −0.0010 (17) |
O2W | 0.061 (3) | 0.060 (2) | 0.040 (2) | 0.023 (2) | 0.0160 (18) | 0.0057 (17) |
O3W | 0.054 (2) | 0.061 (2) | 0.047 (2) | −0.015 (2) | −0.0007 (17) | 0.0173 (19) |
O4W | 0.054 (2) | 0.044 (2) | 0.0359 (18) | 0.0113 (17) | 0.0085 (16) | −0.0011 (15) |
N2 | 0.042 (2) | 0.0304 (19) | 0.035 (2) | 0.0096 (19) | 0.0072 (18) | 0.0031 (19) |
N1 | 0.039 (3) | 0.036 (2) | 0.038 (2) | 0.0101 (18) | 0.0122 (18) | 0.0017 (17) |
O1 | 0.048 (2) | 0.0362 (18) | 0.0361 (18) | 0.0122 (16) | 0.0121 (16) | 0.0027 (15) |
O2 | 0.070 (3) | 0.055 (2) | 0.0340 (18) | 0.028 (2) | 0.0094 (18) | −0.0057 (17) |
O3 | 0.080 (3) | 0.062 (2) | 0.042 (2) | 0.045 (2) | 0.019 (2) | 0.0083 (18) |
O4 | 0.061 (2) | 0.052 (2) | 0.0403 (19) | 0.0296 (19) | 0.0029 (17) | −0.0053 (17) |
O5 | 0.054 (2) | 0.0407 (19) | 0.0385 (19) | 0.0189 (18) | 0.0075 (16) | −0.0045 (16) |
O6 | 0.079 (3) | 0.067 (3) | 0.035 (2) | 0.043 (2) | 0.0014 (19) | −0.0079 (19) |
C1 | 0.039 (3) | 0.030 (2) | 0.037 (3) | 0.004 (2) | 0.008 (2) | 0.004 (2) |
C2 | 0.036 (3) | 0.031 (2) | 0.030 (2) | 0.002 (2) | 0.009 (2) | 0.003 (2) |
C3 | 0.043 (3) | 0.035 (3) | 0.045 (3) | 0.014 (2) | 0.018 (2) | 0.000 (2) |
C4 | 0.071 (4) | 0.052 (3) | 0.033 (3) | 0.025 (3) | 0.014 (3) | 0.003 (3) |
C5 | 0.050 (3) | 0.045 (3) | 0.035 (3) | 0.017 (3) | 0.008 (2) | 0.006 (2) |
C6 | 0.041 (3) | 0.028 (2) | 0.035 (3) | 0.007 (2) | 0.012 (2) | 0.001 (2) |
C7 | 0.043 (3) | 0.031 (2) | 0.037 (3) | 0.003 (2) | 0.017 (2) | 0.004 (2) |
C8 | 0.036 (3) | 0.030 (2) | 0.039 (3) | 0.010 (2) | 0.012 (2) | 0.001 (2) |
C9 | 0.045 (3) | 0.047 (3) | 0.031 (3) | 0.010 (2) | 0.009 (2) | −0.005 (2) |
C10 | 0.055 (3) | 0.048 (3) | 0.026 (2) | 0.015 (3) | 0.004 (2) | 0.004 (2) |
C11 | 0.041 (3) | 0.033 (2) | 0.039 (3) | 0.006 (2) | 0.006 (2) | 0.001 (2) |
C12 | 0.037 (3) | 0.032 (3) | 0.033 (2) | 0.005 (2) | 0.004 (2) | −0.0027 (19) |
C13 | 0.050 (3) | 0.037 (3) | 0.034 (3) | 0.014 (2) | 0.003 (2) | −0.002 (2) |
C14 | 0.038 (3) | 0.039 (3) | 0.038 (3) | 0.012 (2) | 0.003 (2) | −0.002 (2) |
Co1—O1W | 2.037 (3) | O5—C14 | 1.280 (5) |
Co1—O3W | 2.062 (3) | O5—Co1ii | 2.103 (3) |
Co1—O4W | 2.087 (3) | O6—C14 | 1.245 (5) |
Co1—O5i | 2.103 (3) | C1—C2 | 1.497 (6) |
Co1—O1 | 2.110 (3) | C2—C7 | 1.381 (6) |
Co1—O2W | 2.115 (3) | C2—C3 | 1.388 (6) |
O1W—H1WA | 0.8195 | C3—C4 | 1.391 (7) |
O1W—H1WB | 0.8219 | C4—C5 | 1.349 (6) |
O2W—H2WA | 0.8220 | C4—H4 | 0.9300 |
O2W—H2WB | 0.8212 | C5—C6 | 1.397 (6) |
O3W—H3WA | 0.8183 | C5—H5 | 0.9300 |
O3W—H3WB | 0.8089 | C6—C7 | 1.383 (6) |
O4W—H4WA | 0.8158 | C7—H7 | 0.9300 |
O4W—H4WB | 0.8205 | C8—C13 | 1.383 (6) |
N2—N1 | 1.257 (5) | C8—C9 | 1.401 (6) |
N2—C8 | 1.430 (6) | C9—C10 | 1.371 (6) |
N1—C6 | 1.426 (6) | C9—H9 | 0.9300 |
O1—C1 | 1.275 (5) | C10—C11 | 1.385 (6) |
O2—C1 | 1.245 (5) | C10—H10 | 0.9300 |
O3—C3 | 1.357 (5) | C11—C12 | 1.398 (6) |
O3—H3A | 0.8200 | C12—C13 | 1.383 (6) |
O4—C11 | 1.353 (5) | C12—C14 | 1.493 (6) |
O4—H4A | 0.8200 | C13—H13 | 0.9300 |
O1W—Co1—O3W | 177.81 (14) | C3—C2—C1 | 120.9 (4) |
O1W—Co1—O4W | 93.15 (13) | O3—C3—C2 | 122.5 (4) |
O3W—Co1—O4W | 88.88 (13) | O3—C3—C4 | 117.4 (4) |
O1W—Co1—O5i | 88.37 (14) | C2—C3—C4 | 120.2 (4) |
O3W—Co1—O5i | 90.63 (15) | C5—C4—C3 | 119.6 (4) |
O4W—Co1—O5i | 94.86 (12) | C5—C4—H4 | 120.2 |
O1W—Co1—O1 | 89.64 (14) | C3—C4—H4 | 120.2 |
O3W—Co1—O1 | 88.33 (13) | C4—C5—C6 | 121.7 (4) |
O4W—Co1—O1 | 177.14 (13) | C4—C5—H5 | 119.2 |
O5i—Co1—O1 | 84.59 (12) | C6—C5—H5 | 119.2 |
O1W—Co1—O2W | 88.52 (15) | C7—C6—C5 | 118.3 (4) |
O3W—Co1—O2W | 92.42 (15) | C7—C6—N1 | 126.0 (4) |
O4W—Co1—O2W | 87.20 (13) | C5—C6—N1 | 115.6 (4) |
O5i—Co1—O2W | 176.36 (14) | C2—C7—C6 | 120.9 (4) |
O1—Co1—O2W | 93.49 (13) | C2—C7—H7 | 119.6 |
Co1—O1W—H1WA | 129.4 | C6—C7—H7 | 119.6 |
Co1—O1W—H1WB | 113.6 | C13—C8—C9 | 118.6 (4) |
H1WA—O1W—H1WB | 110.0 | C13—C8—N2 | 117.2 (4) |
Co1—O2W—H2WA | 97.5 | C9—C8—N2 | 124.1 (4) |
Co1—O2W—H2WB | 112.9 | C10—C9—C8 | 119.8 (4) |
H2WA—O2W—H2WB | 109.5 | C10—C9—H9 | 120.1 |
Co1—O3W—H3WA | 120.1 | C8—C9—H9 | 120.1 |
Co1—O3W—H3WB | 105.9 | C9—C10—C11 | 120.9 (4) |
H3WA—O3W—H3WB | 111.2 | C9—C10—H10 | 119.5 |
Co1—O4W—H4WA | 125.8 | C11—C10—H10 | 119.5 |
Co1—O4W—H4WB | 101.2 | O4—C11—C10 | 117.4 (4) |
H4WA—O4W—H4WB | 111.2 | O4—C11—C12 | 122.3 (4) |
N1—N2—C8 | 114.1 (3) | C10—C11—C12 | 120.3 (4) |
N2—N1—C6 | 117.2 (4) | C13—C12—C11 | 117.9 (4) |
C1—O1—Co1 | 127.7 (3) | C13—C12—C14 | 120.5 (4) |
C3—O3—H3A | 109.5 | C11—C12—C14 | 121.6 (4) |
C11—O4—H4A | 109.5 | C8—C13—C12 | 122.5 (4) |
C14—O5—Co1ii | 127.3 (3) | C8—C13—H13 | 118.8 |
O2—C1—O1 | 123.7 (4) | C12—C13—H13 | 118.8 |
O2—C1—C2 | 119.4 (4) | O6—C14—O5 | 123.4 (4) |
O1—C1—C2 | 116.9 (4) | O6—C14—C12 | 119.9 (4) |
C7—C2—C3 | 119.3 (4) | O5—C14—C12 | 116.7 (4) |
C7—C2—C1 | 119.8 (4) |
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 |
O1W—H1WA···O6iii | 0.82 | 1.89 | 2.667 (5) | 157 |
O1W—H1WB···N1iv | 0.82 | 2.08 | 2.871 (5) | 161 |
O2W—H2WA···O2 | 0.82 | 1.84 | 2.629 (5) | 161 |
O3W—H3WA···O2iii | 0.82 | 1.88 | 2.682 (4) | 167 |
O3W—H3WB···O4v | 0.81 | 2.23 | 2.899 (5) | 141 |
O4W—H4WA···N2iii | 0.82 | 2.35 | 3.074 (5) | 148 |
O4W—H4WB···O6i | 0.82 | 1.88 | 2.665 (4) | 159 |
O3—H3A···O1 | 0.82 | 1.80 | 2.521 (5) | 147 |
O4—H4A···O5 | 0.82 | 1.82 | 2.541 (4) | 147 |
Symmetry codes: (i) x+1, y−1, z; (iii) −x+1, y−1/2, −z+1/2; (iv) −x+1, −y+1, −z; (v) −x, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | [Co(C14H8N2O6)(H2O)4] |
Mr | 431.22 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 9.5152 (14), 11.2452 (17), 16.194 (2) |
β (°) | 106.687 (2) |
V (Å3) | 1659.8 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.10 |
Crystal size (mm) | 0.10 × 0.08 × 0.08 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.898, 0.918 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11094, 3427, 1976 |
Rint | 0.062 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.133, 0.94 |
No. of reflections | 3427 |
No. of parameters | 246 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.50, −0.44 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1WA···O6i | 0.82 | 1.89 | 2.667 (5) | 156.9 |
O1W—H1WB···N1ii | 0.82 | 2.08 | 2.871 (5) | 161.4 |
O2W—H2WA···O2 | 0.82 | 1.84 | 2.629 (5) | 161.4 |
O3W—H3WA···O2i | 0.82 | 1.88 | 2.682 (4) | 166.9 |
O3W—H3WB···O4iii | 0.81 | 2.23 | 2.899 (5) | 140.6 |
O4W—H4WA···N2i | 0.82 | 2.35 | 3.074 (5) | 147.9 |
O4W—H4WB···O6iv | 0.82 | 1.88 | 2.665 (4) | 159.1 |
O3—H3A···O1 | 0.82 | 1.80 | 2.521 (5) | 146.6 |
O4—H4A···O5 | 0.82 | 1.82 | 2.541 (4) | 146.6 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z; (iii) −x, −y+1, −z; (iv) x+1, y−1, z. |
Olsalazine - 3,3-azobis(6-hydroxybenzoic acid) - has been widely used to prevent and treat the inflammatory bowel diseases, such as ulcerative colitis (Klotz, 2005). In previous work, we have synthesized a serial of Zn (Tang, Tan, Chen & Cao, 2007), Cd and Co (Tang, Yang et al., 2007) complexes with phenanthroline as auxiliary ligand. Also we have reported a Mn complex of olsalazine(Tang, Tan & Cao, 2007), however the cobalt complex with single olsalazine as building block have not been reported yet, Here we reported the crystal structure of the title compound, (I)- a new cobalt complex of olsalazine.
In (I), the Co atom is hexacoordinated (Fig. 1) by two O atoms from two L ligands (H2L=3,3-azo-bis(6-hydroxybenzoic acid)) cis to each other and four water molecules in a distorted octahedral geometry. Each ligand L acts as a carboxylate bridge, that leads to the formation of polymeric chain running in the [-110] direction. Intermolecular O—H···O and O—H···N hydrogen bonds build up a three dimensional supramolecular structure (Table 1).