Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021289/fj2018sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021289/fj2018Isup2.hkl |
CCDC reference: 650532
Key indicators
- Single-crystal X-ray study
- T = 153 K
- Mean (C-C) = 0.004 Å
- R factor = 0.038
- wR factor = 0.149
- Data-to-parameter ratio = 16.9
checkCIF/PLATON results
No syntax errors found
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of N2 = ... S PLAT793_ALERT_1_G Check the Absolute Configuration of N4 = ... S PLAT794_ALERT_5_G Check Predicted Bond Valency for Cr1 (3) 3.17
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 3 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 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
For related literature, see: Choi et al. (2003); Cornman et al. (1992); Cros et al. (1987); Darensbourg et al. (2004); Gabriel et al. (2007); Haber et al. (2003); Li et al. (1988); Plass (1996); Qiu et al. (2004); Taylor (1978); Usman et al. (2003); Vaqueiro et al. (2003); Yang et al. (2004); Zhu, Lin, Meng, Zou & Wang (2003); Zhu, Liu, Wang & Wang (2003).
Single crystals of the title complex suitable for X-ray crystallographic analysis were obtained by solvothermal treatment of CrCl3.6H2O (0.2 mmol) and salicylaldehyde (0.4 mmol),2-hydroxyaminoethylamine (0.4 mmol) and ethanol (3 ml). The reagents were placed in a thick Pyrex tube (ca 20 cm long). The tube was cooled with liquid N2 and the air evacuated. The sealed tube was heated at 353 K for 4 d to yield brown chunk crystals in about 43% yield.
H atoms on the C atoms were positioned geometrically and were allowed to ride on their parent atoms, with C—H = 0.95 Å or 0.99 Å and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C). H atoms on the O and N atoms were located from difference Fourier maps and freely refined.
During the past decades, complexes of N-(2-(2-hydroxyethylamino)ethyl) salicylideneimine Schiff base (sadol) and its derivatives with transition metal have attracted considerable interest because of their potential applications in biological and magnetic properties (Plass, 1996; Cros et al., 1987; Li et al., 1988). Some structurally related complexes of sadol have been reported. These examples include mono-nuclear structures, such as Cd(sadol)2. 2H2O (Yang et al., 2004), [VO(sadol)(acac)] (Li et al., 1988), VO(sadol)(cat) (Cornman et al., 1992), [ZnCl2(sadol)] (Usman et al., 2003) and [Co(sadol)2]Cl (Zhu, et al., 2003), and dimers, as exemplified by [VO2(sadol)]2 (Li et al., 1988), [{Cd(sadol)(ClO4)}2] (Haber et al., 2003) and [{Zn(sadol)}2SO4] (Qiu et al., 2004). As an extension of these studies, we report here the structure of [Cr(C11H15N2O2)2]Cl, (I).
The complex consists of discrete [Cr(sadol)2]+ cations with chloride anions as counterions (Fig. 1, Table 1). The Cr(III) ion is coordinated by four N atoms and two phenoxo O atoms from two sadol ligands to form a slightly distorted octahedron, which can be seen from the trans-angles varying from 172.00 (9) to 172.26 (8) ° and the cis-angles in the range of 81.76 (9)–95.25 (9)°, respectively. Chelation of Cr by the sadol ligand forms a six-membered ring and a five-membered ring, which contribute to the stability of the complex cation. The hydroxy O atom is non-coordinating, mainly because the coordination sphere of the metal ion is completed by two tri-dentate sadol ligands. This phenomenon is observed in Cd(sadol)2.2H2O (Yang et al., 2004) and Co(sadol)2.NO3 (Zhu, et al., 2003). The Cr—O bond distances are 1.9207 (19) Å for Cr1—O1 and 1.929 (2) Å for Cr1—O3 and are shorter than those in other Cr(III) oxygen-containing complexes, (NH4)4 [Cr(C6H4O7)(C6H5O7)].3H2O [1.933 (2)–1.993 (2) Å] (Gabriel et al., 2007), K3[Cr(C2O4)3].3H2O [1.955 (2)–1.985 (2) Å] (Taylor, 1978) and K2[Cr2(C6 H6NO6)2 (OH)2].6H2O [1.937 (4)–1.983 (3) Å] (Choi, 2003). The Cr—N bond lengths ranging from 2.009 (2) to 2.135 (2) Å are in agreement with corresponding bond distances in [Cr(C6H18N4)(SbS3)] (Vaqueiro et al., 2003) and (salen)Cr(III)X (X=Cl, N3) (Darensbourg et al., 2004).
In I, two [Cr(sadol)2]+ cations are linked into a centro-symmetric dimer by four O—H···Cl and two N—H···Cl hydrogen bonds, all involving the Cl anion as the acceptor (Fig. 2).
For related literature, see: Choi et al. (2003); Cornman et al. (1992); Cros et al. (1987); Darensbourg et al. (2004); Gabriel et al. (2007); Haber et al. (2003); Li et al. (1988); Plass (1996); Qiu et al. (2004); Taylor (1978); Usman et al. (2003); Vaqueiro et al. (2003); Yang et al. (2004); Zhu, Lin, Meng, Zou & Wang (2003); Zhu, Liu, Wang & Wang (2003).
Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1995); software used to prepare material for publication: SHELXTL.
[Cr(C11H15N2O2)2]Cl | F(000) = 1052 |
Mr = 501.95 | Dx = 1.477 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 22244 reflections |
a = 9.8883 (3) Å | θ = 3.3–27.5° |
b = 24.6255 (6) Å | µ = 0.66 mm−1 |
c = 10.3494 (4) Å | T = 153 K |
β = 116.388 (1)° | Block, brown |
V = 2257.54 (12) Å3 | 0.15 × 0.13 × 0.09 mm |
Z = 4 |
Rigaku R-AXIS Spider diffractometer | 5165 independent reflections |
Radiation source: Rotating anode | 4097 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
ω scans | θmax = 27.5°, θmin = 3.3° |
Absorption correction: empirical (using intensity measurements) (ABSCOR; Higashi, 1995) | h = −12→12 |
Tmin = 0.907, Tmax = 0.945 | k = −31→31 |
21950 measured reflections | l = −13→13 |
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) = 0.149 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0798P)2 + 2.5978P] where P = (Fo2 + 2Fc2)/3 |
5165 reflections | (Δ/σ)max = 0.001 |
306 parameters | Δρmax = 0.59 e Å−3 |
0 restraints | Δρmin = −0.77 e Å−3 |
[Cr(C11H15N2O2)2]Cl | V = 2257.54 (12) Å3 |
Mr = 501.95 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.8883 (3) Å | µ = 0.66 mm−1 |
b = 24.6255 (6) Å | T = 153 K |
c = 10.3494 (4) Å | 0.15 × 0.13 × 0.09 mm |
β = 116.388 (1)° |
Rigaku R-AXIS Spider diffractometer | 5165 independent reflections |
Absorption correction: empirical (using intensity measurements) (ABSCOR; Higashi, 1995) | 4097 reflections with I > 2σ(I) |
Tmin = 0.907, Tmax = 0.945 | Rint = 0.047 |
21950 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.149 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.59 e Å−3 |
5165 reflections | Δρmin = −0.77 e Å−3 |
306 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 > 2σ(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 | ||
Cr1 | 0.25588 (5) | 0.639340 (16) | 0.37527 (5) | 0.01611 (15) | |
Cl1 | −0.00302 (9) | 0.49037 (3) | 0.19134 (9) | 0.0312 (2) | |
O1 | 0.4222 (2) | 0.67803 (7) | 0.3704 (2) | 0.0216 (4) | |
O2 | −0.2439 (3) | 0.55214 (9) | 0.2622 (3) | 0.0319 (5) | |
O3 | 0.2469 (2) | 0.68784 (7) | 0.5176 (2) | 0.0204 (4) | |
O4 | 0.3031 (3) | 0.48259 (9) | 0.1011 (3) | 0.0351 (6) | |
N1 | 0.4013 (3) | 0.58897 (9) | 0.5279 (3) | 0.0192 (5) | |
N2 | 0.0960 (3) | 0.59080 (9) | 0.4053 (3) | 0.0189 (5) | |
N3 | 0.1005 (3) | 0.68405 (9) | 0.2162 (3) | 0.0191 (5) | |
N4 | 0.2410 (3) | 0.59186 (9) | 0.1968 (3) | 0.0195 (5) | |
C1 | 0.5654 (3) | 0.67774 (10) | 0.4665 (3) | 0.0190 (5) | |
C2 | 0.6616 (3) | 0.71784 (11) | 0.4563 (3) | 0.0235 (6) | |
H2A | 0.6216 | 0.7442 | 0.3816 | 0.028* | |
C3 | 0.8124 (3) | 0.71979 (12) | 0.5522 (4) | 0.0291 (7) | |
H3A | 0.8744 | 0.7476 | 0.5435 | 0.035* | |
C4 | 0.8749 (3) | 0.68135 (13) | 0.6616 (4) | 0.0298 (7) | |
H4A | 0.9793 | 0.6826 | 0.7269 | 0.036* | |
C5 | 0.7842 (3) | 0.64169 (12) | 0.6740 (3) | 0.0267 (6) | |
H5A | 0.8270 | 0.6154 | 0.7484 | 0.032* | |
C6 | 0.6293 (3) | 0.63902 (11) | 0.5792 (3) | 0.0204 (6) | |
C7 | 0.5446 (3) | 0.59572 (11) | 0.6021 (3) | 0.0211 (6) | |
H7A | 0.5979 | 0.5704 | 0.6770 | 0.025* | |
C8 | 0.3264 (3) | 0.54421 (11) | 0.5645 (3) | 0.0257 (6) | |
H8A | 0.3898 | 0.5315 | 0.6641 | 0.031* | |
H8B | 0.3087 | 0.5134 | 0.4975 | 0.031* | |
C9 | 0.1781 (3) | 0.56623 (11) | 0.5511 (3) | 0.0246 (6) | |
H9A | 0.1173 | 0.5366 | 0.5637 | 0.029* | |
H9B | 0.1965 | 0.5940 | 0.6263 | 0.029* | |
C10 | −0.0439 (3) | 0.61895 (11) | 0.3877 (3) | 0.0241 (6) | |
H10A | −0.0862 | 0.6387 | 0.2948 | 0.029* | |
H10B | −0.0168 | 0.6463 | 0.4655 | 0.029* | |
C11 | −0.1655 (3) | 0.58246 (11) | 0.3909 (3) | 0.0251 (6) | |
H11A | −0.1188 | 0.5569 | 0.4729 | 0.030* | |
H11B | −0.2390 | 0.6050 | 0.4078 | 0.030* | |
C12 | 0.1824 (3) | 0.73617 (10) | 0.4983 (3) | 0.0202 (6) | |
C13 | 0.1971 (3) | 0.76508 (11) | 0.6207 (3) | 0.0235 (6) | |
H13A | 0.2506 | 0.7491 | 0.7133 | 0.028* | |
C14 | 0.1356 (3) | 0.81617 (12) | 0.6095 (4) | 0.0267 (6) | |
H14A | 0.1479 | 0.8349 | 0.6943 | 0.032* | |
C15 | 0.0555 (4) | 0.84056 (12) | 0.4752 (4) | 0.0296 (7) | |
H15A | 0.0158 | 0.8762 | 0.4680 | 0.035* | |
C16 | 0.0350 (3) | 0.81254 (11) | 0.3542 (4) | 0.0266 (6) | |
H16A | −0.0224 | 0.8285 | 0.2622 | 0.032* | |
C17 | 0.0974 (3) | 0.76009 (10) | 0.3626 (3) | 0.0202 (6) | |
C18 | 0.0578 (3) | 0.73256 (10) | 0.2282 (3) | 0.0195 (5) | |
H18A | −0.0044 | 0.7514 | 0.1419 | 0.023* | |
C19 | 0.0393 (3) | 0.65791 (11) | 0.0744 (3) | 0.0221 (6) | |
H19A | −0.0012 | 0.6856 | −0.0028 | 0.027* | |
H19B | −0.0436 | 0.6329 | 0.0630 | 0.027* | |
C20 | 0.1661 (3) | 0.62671 (11) | 0.0640 (3) | 0.0224 (6) | |
H20A | 0.1254 | 0.6037 | −0.0235 | 0.027* | |
H20B | 0.2403 | 0.6523 | 0.0578 | 0.027* | |
C21 | 0.3885 (3) | 0.57035 (12) | 0.2107 (3) | 0.0258 (6) | |
H21A | 0.4408 | 0.5517 | 0.3049 | 0.031* | |
H21B | 0.4523 | 0.6014 | 0.2109 | 0.031* | |
C22 | 0.3754 (3) | 0.53118 (12) | 0.0926 (3) | 0.0274 (6) | |
H22A | 0.3167 | 0.5483 | −0.0028 | 0.033* | |
H22B | 0.4773 | 0.5227 | 0.1023 | 0.033* | |
H2O | −0.180 (5) | 0.5348 (18) | 0.242 (5) | 0.053 (13)* | |
H4O | 0.220 (5) | 0.4791 (16) | 0.044 (5) | 0.038 (12)* | |
H2N | 0.072 (4) | 0.5629 (13) | 0.347 (4) | 0.018 (8)* | |
H4N | 0.187 (4) | 0.5638 (15) | 0.188 (4) | 0.030 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cr1 | 0.0146 (2) | 0.0155 (2) | 0.0183 (2) | 0.00028 (14) | 0.00737 (18) | 0.00112 (15) |
Cl1 | 0.0317 (4) | 0.0273 (4) | 0.0337 (4) | −0.0050 (3) | 0.0138 (3) | −0.0070 (3) |
O1 | 0.0149 (9) | 0.0214 (9) | 0.0269 (10) | −0.0021 (7) | 0.0077 (8) | 0.0030 (8) |
O2 | 0.0215 (11) | 0.0381 (12) | 0.0356 (13) | −0.0032 (9) | 0.0122 (10) | −0.0023 (10) |
O3 | 0.0223 (10) | 0.0183 (9) | 0.0196 (9) | 0.0023 (7) | 0.0085 (8) | 0.0011 (7) |
O4 | 0.0370 (14) | 0.0282 (11) | 0.0336 (13) | 0.0027 (10) | 0.0099 (11) | 0.0004 (10) |
N1 | 0.0181 (11) | 0.0179 (10) | 0.0231 (12) | 0.0024 (8) | 0.0104 (9) | 0.0018 (9) |
N2 | 0.0174 (11) | 0.0175 (10) | 0.0234 (12) | 0.0004 (8) | 0.0106 (9) | 0.0010 (9) |
N3 | 0.0164 (11) | 0.0207 (10) | 0.0202 (11) | −0.0006 (8) | 0.0081 (9) | 0.0007 (9) |
N4 | 0.0183 (11) | 0.0182 (10) | 0.0222 (12) | −0.0005 (9) | 0.0089 (9) | −0.0016 (9) |
C1 | 0.0156 (12) | 0.0204 (12) | 0.0237 (14) | 0.0000 (9) | 0.0113 (11) | −0.0038 (10) |
C2 | 0.0229 (14) | 0.0213 (12) | 0.0298 (15) | −0.0022 (10) | 0.0150 (12) | −0.0013 (11) |
C3 | 0.0256 (15) | 0.0279 (14) | 0.0383 (17) | −0.0078 (12) | 0.0182 (14) | −0.0097 (13) |
C4 | 0.0183 (14) | 0.0370 (16) | 0.0307 (16) | −0.0056 (12) | 0.0077 (12) | −0.0071 (13) |
C5 | 0.0225 (14) | 0.0328 (15) | 0.0234 (14) | 0.0014 (12) | 0.0089 (12) | −0.0002 (12) |
C6 | 0.0215 (14) | 0.0246 (13) | 0.0160 (13) | −0.0006 (10) | 0.0090 (11) | −0.0027 (10) |
C7 | 0.0196 (13) | 0.0208 (12) | 0.0220 (13) | 0.0042 (10) | 0.0085 (11) | 0.0014 (10) |
C8 | 0.0207 (14) | 0.0212 (13) | 0.0339 (16) | 0.0017 (10) | 0.0109 (12) | 0.0119 (12) |
C9 | 0.0249 (14) | 0.0246 (13) | 0.0261 (15) | −0.0001 (11) | 0.0130 (12) | 0.0085 (11) |
C10 | 0.0190 (13) | 0.0212 (12) | 0.0351 (16) | 0.0028 (10) | 0.0148 (12) | 0.0055 (12) |
C11 | 0.0221 (14) | 0.0248 (13) | 0.0327 (16) | 0.0025 (11) | 0.0161 (12) | 0.0069 (12) |
C12 | 0.0150 (12) | 0.0186 (12) | 0.0281 (15) | −0.0030 (10) | 0.0107 (11) | −0.0010 (10) |
C13 | 0.0197 (13) | 0.0265 (13) | 0.0237 (14) | −0.0016 (11) | 0.0091 (11) | −0.0030 (11) |
C14 | 0.0236 (14) | 0.0274 (14) | 0.0315 (16) | −0.0032 (11) | 0.0144 (13) | −0.0087 (12) |
C15 | 0.0322 (16) | 0.0198 (13) | 0.0373 (17) | 0.0030 (12) | 0.0160 (14) | −0.0022 (12) |
C16 | 0.0274 (15) | 0.0204 (13) | 0.0336 (16) | 0.0026 (11) | 0.0149 (13) | 0.0037 (12) |
C17 | 0.0196 (13) | 0.0170 (12) | 0.0274 (14) | −0.0002 (10) | 0.0134 (11) | 0.0020 (10) |
C18 | 0.0182 (12) | 0.0206 (12) | 0.0226 (13) | 0.0001 (10) | 0.0117 (11) | 0.0039 (10) |
C19 | 0.0200 (13) | 0.0244 (13) | 0.0163 (13) | 0.0025 (11) | 0.0030 (11) | 0.0005 (11) |
C20 | 0.0271 (14) | 0.0256 (13) | 0.0143 (12) | 0.0020 (11) | 0.0090 (11) | −0.0017 (11) |
C21 | 0.0189 (13) | 0.0301 (14) | 0.0272 (15) | 0.0030 (11) | 0.0092 (12) | −0.0047 (12) |
C22 | 0.0257 (15) | 0.0317 (15) | 0.0261 (15) | 0.0041 (12) | 0.0128 (13) | −0.0033 (12) |
Cr1—O1 | 1.9207 (19) | C7—H7A | 0.9500 |
Cr1—O3 | 1.929 (2) | C8—C9 | 1.512 (4) |
Cr1—N3 | 2.009 (2) | C8—H8A | 0.9900 |
Cr1—N1 | 2.020 (2) | C8—H8B | 0.9900 |
Cr1—N2 | 2.112 (2) | C9—H9A | 0.9900 |
Cr1—N4 | 2.135 (2) | C9—H9B | 0.9900 |
O1—C1 | 1.321 (3) | C10—C11 | 1.513 (4) |
O2—C11 | 1.419 (4) | C10—H10A | 0.9900 |
O2—H2O | 0.86 (5) | C10—H10B | 0.9900 |
O3—C12 | 1.323 (3) | C11—H11A | 0.9900 |
O4—C22 | 1.417 (4) | C11—H11B | 0.9900 |
O4—H4O | 0.78 (4) | C12—C13 | 1.404 (4) |
N1—C7 | 1.288 (4) | C12—C17 | 1.406 (4) |
N1—C8 | 1.468 (3) | C13—C14 | 1.380 (4) |
N2—C10 | 1.485 (3) | C13—H13A | 0.9500 |
N2—C9 | 1.488 (4) | C14—C15 | 1.394 (5) |
N2—H2N | 0.87 (3) | C14—H14A | 0.9500 |
N3—C18 | 1.292 (3) | C15—C16 | 1.364 (4) |
N3—C19 | 1.465 (3) | C15—H15A | 0.9500 |
N4—C21 | 1.497 (4) | C16—C17 | 1.417 (4) |
N4—C20 | 1.506 (3) | C16—H16A | 0.9500 |
N4—H4N | 0.85 (4) | C17—C18 | 1.436 (4) |
C1—C2 | 1.407 (4) | C18—H18A | 0.9500 |
C1—C6 | 1.419 (4) | C19—C20 | 1.514 (4) |
C2—C3 | 1.377 (4) | C19—H19A | 0.9900 |
C2—H2A | 0.9500 | C19—H19B | 0.9900 |
C3—C4 | 1.392 (5) | C20—H20A | 0.9900 |
C3—H3A | 0.9500 | C20—H20B | 0.9900 |
C4—C5 | 1.370 (4) | C21—C22 | 1.517 (4) |
C4—H4A | 0.9500 | C21—H21A | 0.9900 |
C5—C6 | 1.406 (4) | C21—H21B | 0.9900 |
C5—H5A | 0.9500 | C22—H22A | 0.9900 |
C6—C7 | 1.439 (4) | C22—H22B | 0.9900 |
O1—Cr1—O3 | 92.51 (9) | N2—C9—C8 | 107.9 (2) |
O1—Cr1—N3 | 93.34 (9) | N2—C9—H9A | 110.1 |
O3—Cr1—N3 | 90.50 (9) | C8—C9—H9A | 110.1 |
O1—Cr1—N1 | 90.29 (9) | N2—C9—H9B | 110.1 |
O3—Cr1—N1 | 92.37 (9) | C8—C9—H9B | 110.1 |
N3—Cr1—N1 | 175.27 (9) | H9A—C9—H9B | 108.4 |
O1—Cr1—N2 | 172.00 (9) | N2—C10—C11 | 115.2 (2) |
O3—Cr1—N2 | 86.94 (9) | N2—C10—H10A | 108.5 |
N3—Cr1—N2 | 94.65 (9) | C11—C10—H10A | 108.5 |
N1—Cr1—N2 | 81.76 (9) | N2—C10—H10B | 108.5 |
O1—Cr1—N4 | 88.80 (9) | C11—C10—H10B | 108.5 |
O3—Cr1—N4 | 172.26 (8) | H10A—C10—H10B | 107.5 |
N3—Cr1—N4 | 81.80 (9) | O2—C11—C10 | 113.6 (3) |
N1—Cr1—N4 | 95.25 (9) | O2—C11—H11A | 108.9 |
N2—Cr1—N4 | 92.81 (9) | C10—C11—H11A | 108.9 |
C1—O1—Cr1 | 128.43 (18) | O2—C11—H11B | 108.9 |
C11—O2—H2O | 109 (3) | C10—C11—H11B | 108.9 |
C12—O3—Cr1 | 128.60 (18) | H11A—C11—H11B | 107.7 |
C22—O4—H4O | 116 (3) | O3—C12—C13 | 118.0 (3) |
C7—N1—C8 | 119.3 (2) | O3—C12—C17 | 124.2 (3) |
C7—N1—Cr1 | 126.83 (19) | C13—C12—C17 | 117.7 (2) |
C8—N1—Cr1 | 113.43 (17) | C14—C13—C12 | 121.5 (3) |
C10—N2—C9 | 111.8 (2) | C14—C13—H13A | 119.3 |
C10—N2—Cr1 | 115.81 (16) | C12—C13—H13A | 119.3 |
C9—N2—Cr1 | 105.84 (17) | C13—C14—C15 | 120.7 (3) |
C10—N2—H2N | 109 (2) | C13—C14—H14A | 119.7 |
C9—N2—H2N | 104 (2) | C15—C14—H14A | 119.7 |
Cr1—N2—H2N | 110 (2) | C16—C15—C14 | 119.0 (3) |
C18—N3—C19 | 119.7 (2) | C16—C15—H15A | 120.5 |
C18—N3—Cr1 | 126.3 (2) | C14—C15—H15A | 120.5 |
C19—N3—Cr1 | 113.92 (17) | C15—C16—C17 | 121.4 (3) |
C21—N4—C20 | 110.7 (2) | C15—C16—H16A | 119.3 |
C21—N4—Cr1 | 114.89 (17) | C17—C16—H16A | 119.3 |
C20—N4—Cr1 | 107.10 (16) | C12—C17—C16 | 119.6 (3) |
C21—N4—H4N | 105 (2) | C12—C17—C18 | 123.6 (2) |
C20—N4—H4N | 109 (3) | C16—C17—C18 | 116.6 (3) |
Cr1—N4—H4N | 110 (3) | N3—C18—C17 | 124.8 (3) |
O1—C1—C2 | 118.3 (2) | N3—C18—H18A | 117.6 |
O1—C1—C6 | 124.0 (2) | C17—C18—H18A | 117.6 |
C2—C1—C6 | 117.7 (3) | N3—C19—C20 | 107.9 (2) |
C3—C2—C1 | 121.5 (3) | N3—C19—H19A | 110.1 |
C3—C2—H2A | 119.3 | C20—C19—H19A | 110.1 |
C1—C2—H2A | 119.3 | N3—C19—H19B | 110.1 |
C2—C3—C4 | 120.6 (3) | C20—C19—H19B | 110.1 |
C2—C3—H3A | 119.7 | H19A—C19—H19B | 108.4 |
C4—C3—H3A | 119.7 | N4—C20—C19 | 108.2 (2) |
C5—C4—C3 | 119.2 (3) | N4—C20—H20A | 110.1 |
C5—C4—H4A | 120.4 | C19—C20—H20A | 110.1 |
C3—C4—H4A | 120.4 | N4—C20—H20B | 110.1 |
C4—C5—C6 | 121.6 (3) | C19—C20—H20B | 110.1 |
C4—C5—H5A | 119.2 | H20A—C20—H20B | 108.4 |
C6—C5—H5A | 119.2 | N4—C21—C22 | 114.6 (2) |
C5—C6—C1 | 119.4 (3) | N4—C21—H21A | 108.6 |
C5—C6—C7 | 116.9 (3) | C22—C21—H21A | 108.6 |
C1—C6—C7 | 123.7 (3) | N4—C21—H21B | 108.6 |
N1—C7—C6 | 124.3 (3) | C22—C21—H21B | 108.6 |
N1—C7—H7A | 117.8 | H21A—C21—H21B | 107.6 |
C6—C7—H7A | 117.8 | O4—C22—C21 | 110.6 (3) |
N1—C8—C9 | 106.7 (2) | O4—C22—H22A | 109.5 |
N1—C8—H8A | 110.4 | C21—C22—H22A | 109.5 |
C9—C8—H8A | 110.4 | O4—C22—H22B | 109.5 |
N1—C8—H8B | 110.4 | C21—C22—H22B | 109.5 |
C9—C8—H8B | 110.4 | H22A—C22—H22B | 108.1 |
H8A—C8—H8B | 108.6 | ||
O3—Cr1—O1—C1 | 75.1 (2) | C2—C3—C4—C5 | −0.7 (5) |
N3—Cr1—O1—C1 | 165.7 (2) | C3—C4—C5—C6 | −0.3 (5) |
N1—Cr1—O1—C1 | −17.3 (2) | C4—C5—C6—C1 | 1.0 (4) |
N4—Cr1—O1—C1 | −112.5 (2) | C4—C5—C6—C7 | −179.9 (3) |
O1—Cr1—O3—C12 | 81.4 (2) | O1—C1—C6—C5 | 178.5 (3) |
N3—Cr1—O3—C12 | −12.0 (2) | C2—C1—C6—C5 | −0.8 (4) |
N1—Cr1—O3—C12 | 171.8 (2) | O1—C1—C6—C7 | −0.4 (4) |
N2—Cr1—O3—C12 | −106.6 (2) | C2—C1—C6—C7 | −179.7 (3) |
O1—Cr1—N1—C7 | 13.2 (2) | C8—N1—C7—C6 | −178.0 (3) |
O3—Cr1—N1—C7 | −79.3 (2) | Cr1—N1—C7—C6 | −5.9 (4) |
N2—Cr1—N1—C7 | −165.8 (3) | C5—C6—C7—N1 | 177.5 (3) |
N4—Cr1—N1—C7 | 102.1 (2) | C1—C6—C7—N1 | −3.5 (4) |
O1—Cr1—N1—C8 | −174.3 (2) | C7—N1—C8—C9 | 139.3 (3) |
O3—Cr1—N1—C8 | 93.2 (2) | Cr1—N1—C8—C9 | −33.8 (3) |
N2—Cr1—N1—C8 | 6.7 (2) | C10—N2—C9—C8 | −173.7 (2) |
N4—Cr1—N1—C8 | −85.4 (2) | Cr1—N2—C9—C8 | −46.8 (2) |
O3—Cr1—N2—C10 | 53.9 (2) | N1—C8—C9—N2 | 53.2 (3) |
N3—Cr1—N2—C10 | −36.3 (2) | C9—N2—C10—C11 | −66.0 (3) |
N1—Cr1—N2—C10 | 146.8 (2) | Cr1—N2—C10—C11 | 172.7 (2) |
N4—Cr1—N2—C10 | −118.3 (2) | N2—C10—C11—O2 | −75.3 (3) |
O3—Cr1—N2—C9 | −70.60 (17) | Cr1—O3—C12—C13 | −177.08 (19) |
N3—Cr1—N2—C9 | −160.85 (18) | Cr1—O3—C12—C17 | 4.3 (4) |
N1—Cr1—N2—C9 | 22.25 (17) | O3—C12—C13—C14 | 178.8 (3) |
N4—Cr1—N2—C9 | 117.15 (18) | C17—C12—C13—C14 | −2.5 (4) |
O1—Cr1—N3—C18 | −77.8 (2) | C12—C13—C14—C15 | 0.4 (5) |
O3—Cr1—N3—C18 | 14.7 (2) | C13—C14—C15—C16 | 1.9 (5) |
N2—Cr1—N3—C18 | 101.7 (2) | C14—C15—C16—C17 | −2.1 (5) |
N4—Cr1—N3—C18 | −166.1 (2) | O3—C12—C17—C16 | −179.1 (3) |
O1—Cr1—N3—C19 | 99.16 (19) | C13—C12—C17—C16 | 2.3 (4) |
O3—Cr1—N3—C19 | −168.30 (19) | O3—C12—C17—C18 | 6.4 (4) |
N2—Cr1—N3—C19 | −81.33 (19) | C13—C12—C17—C18 | −172.2 (3) |
N4—Cr1—N3—C19 | 10.85 (19) | C15—C16—C17—C12 | 0.0 (4) |
O1—Cr1—N4—C21 | 46.7 (2) | C15—C16—C17—C18 | 174.8 (3) |
N3—Cr1—N4—C21 | 140.2 (2) | C19—N3—C18—C17 | 173.2 (3) |
N1—Cr1—N4—C21 | −43.5 (2) | Cr1—N3—C18—C17 | −10.0 (4) |
N2—Cr1—N4—C21 | −125.5 (2) | C12—C17—C18—N3 | −3.1 (4) |
O1—Cr1—N4—C20 | −76.64 (18) | C16—C17—C18—N3 | −177.7 (3) |
N3—Cr1—N4—C20 | 16.91 (17) | C18—N3—C19—C20 | 140.8 (3) |
N1—Cr1—N4—C20 | −166.82 (18) | Cr1—N3—C19—C20 | −36.4 (3) |
N2—Cr1—N4—C20 | 111.20 (18) | C21—N4—C20—C19 | −166.5 (2) |
Cr1—O1—C1—C2 | −166.48 (19) | Cr1—N4—C20—C19 | −40.6 (2) |
Cr1—O1—C1—C6 | 14.2 (4) | N3—C19—C20—N4 | 50.4 (3) |
O1—C1—C2—C3 | −179.5 (3) | C20—N4—C21—C22 | −65.6 (3) |
C6—C1—C2—C3 | −0.2 (4) | Cr1—N4—C21—C22 | 173.0 (2) |
C1—C2—C3—C4 | 0.9 (5) | N4—C21—C22—O4 | −66.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2O···Cl1 | 0.86 (5) | 2.31 (5) | 3.175 (3) | 178 (4) |
O4—H4O···Cl1i | 0.78 (4) | 2.54 (4) | 3.229 (3) | 149 (4) |
N4—H4N···Cl1 | 0.85 (4) | 2.62 (4) | 3.457 (3) | 168 (4) |
N2—H2N···Cl1 | 0.87 (3) | 2.30 (3) | 3.170 (2) | 177 (3) |
Symmetry code: (i) −x, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | [Cr(C11H15N2O2)2]Cl |
Mr | 501.95 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 153 |
a, b, c (Å) | 9.8883 (3), 24.6255 (6), 10.3494 (4) |
β (°) | 116.388 (1) |
V (Å3) | 2257.54 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.66 |
Crystal size (mm) | 0.15 × 0.13 × 0.09 |
Data collection | |
Diffractometer | Rigaku R-AXIS Spider |
Absorption correction | Empirical (using intensity measurements) (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.907, 0.945 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21950, 5165, 4097 |
Rint | 0.047 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.149, 1.06 |
No. of reflections | 5165 |
No. of parameters | 306 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.59, −0.77 |
Computer programs: RAPID-AUTO (Rigaku, 2004), RAPID-AUTO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1995), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2O···Cl1 | 0.86 (5) | 2.31 (5) | 3.175 (3) | 178 (4) |
O4—H4O···Cl1i | 0.78 (4) | 2.54 (4) | 3.229 (3) | 149 (4) |
N4—H4N···Cl1 | 0.85 (4) | 2.62 (4) | 3.457 (3) | 168 (4) |
N2—H2N···Cl1 | 0.87 (3) | 2.30 (3) | 3.170 (2) | 177 (3) |
Symmetry code: (i) −x, −y+1, −z. |
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During the past decades, complexes of N-(2-(2-hydroxyethylamino)ethyl) salicylideneimine Schiff base (sadol) and its derivatives with transition metal have attracted considerable interest because of their potential applications in biological and magnetic properties (Plass, 1996; Cros et al., 1987; Li et al., 1988). Some structurally related complexes of sadol have been reported. These examples include mono-nuclear structures, such as Cd(sadol)2. 2H2O (Yang et al., 2004), [VO(sadol)(acac)] (Li et al., 1988), VO(sadol)(cat) (Cornman et al., 1992), [ZnCl2(sadol)] (Usman et al., 2003) and [Co(sadol)2]Cl (Zhu, et al., 2003), and dimers, as exemplified by [VO2(sadol)]2 (Li et al., 1988), [{Cd(sadol)(ClO4)}2] (Haber et al., 2003) and [{Zn(sadol)}2SO4] (Qiu et al., 2004). As an extension of these studies, we report here the structure of [Cr(C11H15N2O2)2]Cl, (I).
The complex consists of discrete [Cr(sadol)2]+ cations with chloride anions as counterions (Fig. 1, Table 1). The Cr(III) ion is coordinated by four N atoms and two phenoxo O atoms from two sadol ligands to form a slightly distorted octahedron, which can be seen from the trans-angles varying from 172.00 (9) to 172.26 (8) ° and the cis-angles in the range of 81.76 (9)–95.25 (9)°, respectively. Chelation of Cr by the sadol ligand forms a six-membered ring and a five-membered ring, which contribute to the stability of the complex cation. The hydroxy O atom is non-coordinating, mainly because the coordination sphere of the metal ion is completed by two tri-dentate sadol ligands. This phenomenon is observed in Cd(sadol)2.2H2O (Yang et al., 2004) and Co(sadol)2.NO3 (Zhu, et al., 2003). The Cr—O bond distances are 1.9207 (19) Å for Cr1—O1 and 1.929 (2) Å for Cr1—O3 and are shorter than those in other Cr(III) oxygen-containing complexes, (NH4)4 [Cr(C6H4O7)(C6H5O7)].3H2O [1.933 (2)–1.993 (2) Å] (Gabriel et al., 2007), K3[Cr(C2O4)3].3H2O [1.955 (2)–1.985 (2) Å] (Taylor, 1978) and K2[Cr2(C6 H6NO6)2 (OH)2].6H2O [1.937 (4)–1.983 (3) Å] (Choi, 2003). The Cr—N bond lengths ranging from 2.009 (2) to 2.135 (2) Å are in agreement with corresponding bond distances in [Cr(C6H18N4)(SbS3)] (Vaqueiro et al., 2003) and (salen)Cr(III)X (X=Cl, N3) (Darensbourg et al., 2004).
In I, two [Cr(sadol)2]+ cations are linked into a centro-symmetric dimer by four O—H···Cl and two N—H···Cl hydrogen bonds, all involving the Cl anion as the acceptor (Fig. 2).