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Acta Cryst. (2007). E63, m1580-m1581    [ doi:10.1107/S1600536807021289 ]

Bis{N-[2-(2-hydroxyethylamino)ethyl]salicylideneiminato-[kappa]3O,N,N'}chromium(III) chloride

Y.-Z. Yuan, J. Zhou and X. Liu

Abstract top

In the title complex, [Cr(C11H15N2O2)2]Cl, the CrIII ion is coordinated by four N atoms and two O atoms from two tridentate N-[2-(2-hydroxyethylamino)ethyl]salicylideneimine (sadol) ligands to form a distorted octahedron. A centrosymmetric dimer is constructed through the formation of O-H...Cl and N-H...Cl hydrogen bonds.

Comment top

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).

Related literature top

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).

Experimental top

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.

Refinement top

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.

Computing details top

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.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level, and all H atoms are omitted for clarity.
[Figure 2] Fig. 2. The centrosymmetric dimer constructed by the combination of O—H···Cl and N—H···Cl hydrogen bonds. [Symmetry code: (i) -x, -y + 1, -z.]
Bis{N-[2-(2-hydroxyethylamino)ethyl]salicylideneimine-κ3O,N,N'} chromium(III) chloride top
Crystal data top
[Cr(C11H15N2O2)2]ClF(000) = 1052
Mr = 501.95Dx = 1.477 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 22244 reflections
a = 9.8883 (3) Åθ = 3.3–27.5°
b = 24.6255 (6) ŵ = 0.66 mm−1
c = 10.3494 (4) ÅT = 153 K
β = 116.388 (1)°Block, brown
V = 2257.54 (12) Å30.15 × 0.13 × 0.09 mm
Z = 4
Data collection top
Rigaku R-AXIS Spider
diffractometer		5165 independent reflections
Radiation source: Rotating anode4097 reflections with I > 2σ(I)
graphiteRint = 0.047
ω scansθmax = 27.5°, θmin = 3.3°
Absorption correction: empirical (using intensity measurements)
(ABSCOR; Higashi, 1995)		h = −12→12
Tmin = 0.907, Tmax = 0.945k = −31→31
21950 measured reflectionsl = −13→13
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149H 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 parametersΔρmax = 0.59 e Å−3
0 restraintsΔρmin = −0.77 e Å−3
Crystal data top
[Cr(C11H15N2O2)2]ClV = 2257.54 (12) Å3
Mr = 501.95Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.8883 (3) ŵ = 0.66 mm−1
b = 24.6255 (6) ÅT = 153 K
c = 10.3494 (4) Å0.15 × 0.13 × 0.09 mm
β = 116.388 (1)°
Data collection top
Rigaku R-AXIS Spider
diffractometer		4097 reflections with I > 2σ(I)
Absorption correction: empirical (using intensity measurements)
(ABSCOR; Higashi, 1995)		Rint = 0.047
Tmin = 0.907, Tmax = 0.945θmax = 27.5°
21950 measured reflectionsStandard reflections: 0
5165 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.038H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.149Δρmax = 0.59 e Å−3
S = 1.06Δρmin = −0.77 e Å−3
5165 reflectionsAbsolute structure: ?
306 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cr10.25588 (5)0.639340 (16)0.37527 (5)0.01611 (15)
Cl1−0.00302 (9)0.49037 (3)0.19134 (9)0.0312 (2)
O10.4222 (2)0.67803 (7)0.3704 (2)0.0216 (4)
O2−0.2439 (3)0.55214 (9)0.2622 (3)0.0319 (5)
O30.2469 (2)0.68784 (7)0.5176 (2)0.0204 (4)
O40.3031 (3)0.48259 (9)0.1011 (3)0.0351 (6)
N10.4013 (3)0.58897 (9)0.5279 (3)0.0192 (5)
N20.0960 (3)0.59080 (9)0.4053 (3)0.0189 (5)
N30.1005 (3)0.68405 (9)0.2162 (3)0.0191 (5)
N40.2410 (3)0.59186 (9)0.1968 (3)0.0195 (5)
C10.5654 (3)0.67774 (10)0.4665 (3)0.0190 (5)
C20.6616 (3)0.71784 (11)0.4563 (3)0.0235 (6)
H2A0.62160.74420.38160.028*
C30.8124 (3)0.71979 (12)0.5522 (4)0.0291 (7)
H3A0.87440.74760.54350.035*
C40.8749 (3)0.68135 (13)0.6616 (4)0.0298 (7)
H4A0.97930.68260.72690.036*
C50.7842 (3)0.64169 (12)0.6740 (3)0.0267 (6)
H5A0.82700.61540.74840.032*
C60.6293 (3)0.63902 (11)0.5792 (3)0.0204 (6)
C70.5446 (3)0.59572 (11)0.6021 (3)0.0211 (6)
H7A0.59790.57040.67700.025*
C80.3264 (3)0.54421 (11)0.5645 (3)0.0257 (6)
H8A0.38980.53150.66410.031*
H8B0.30870.51340.49750.031*
C90.1781 (3)0.56623 (11)0.5511 (3)0.0246 (6)
H9A0.11730.53660.56370.029*
H9B0.19650.59400.62630.029*
C10−0.0439 (3)0.61895 (11)0.3877 (3)0.0241 (6)
H10A−0.08620.63870.29480.029*
H10B−0.01680.64630.46550.029*
C11−0.1655 (3)0.58246 (11)0.3909 (3)0.0251 (6)
H11A−0.11880.55690.47290.030*
H11B−0.23900.60500.40780.030*
C120.1824 (3)0.73617 (10)0.4983 (3)0.0202 (6)
C130.1971 (3)0.76508 (11)0.6207 (3)0.0235 (6)
H13A0.25060.74910.71330.028*
C140.1356 (3)0.81617 (12)0.6095 (4)0.0267 (6)
H14A0.14790.83490.69430.032*
C150.0555 (4)0.84056 (12)0.4752 (4)0.0296 (7)
H15A0.01580.87620.46800.035*
C160.0350 (3)0.81254 (11)0.3542 (4)0.0266 (6)
H16A−0.02240.82850.26220.032*
C170.0974 (3)0.76009 (10)0.3626 (3)0.0202 (6)
C180.0578 (3)0.73256 (10)0.2282 (3)0.0195 (5)
H18A−0.00440.75140.14190.023*
C190.0393 (3)0.65791 (11)0.0744 (3)0.0221 (6)
H19A−0.00120.6856−0.00280.027*
H19B−0.04360.63290.06300.027*
C200.1661 (3)0.62671 (11)0.0640 (3)0.0224 (6)
H20A0.12540.6037−0.02350.027*
H20B0.24030.65230.05780.027*
C210.3885 (3)0.57035 (12)0.2107 (3)0.0258 (6)
H21A0.44080.55170.30490.031*
H21B0.45230.60140.21090.031*
C220.3754 (3)0.53118 (12)0.0926 (3)0.0274 (6)
H22A0.31670.5483−0.00280.033*
H22B0.47730.52270.10230.033*
H2O−0.180 (5)0.5348 (18)0.242 (5)0.053 (13)*
H4O0.220 (5)0.4791 (16)0.044 (5)0.038 (12)*
H2N0.072 (4)0.5629 (13)0.347 (4)0.018 (8)*
H4N0.187 (4)0.5638 (15)0.188 (4)0.030 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cr10.0146 (2)0.0155 (2)0.0183 (2)0.00028 (14)0.00737 (18)0.00112 (15)
Cl10.0317 (4)0.0273 (4)0.0337 (4)−0.0050 (3)0.0138 (3)−0.0070 (3)
O10.0149 (9)0.0214 (9)0.0269 (10)−0.0021 (7)0.0077 (8)0.0030 (8)
O20.0215 (11)0.0381 (12)0.0356 (13)−0.0032 (9)0.0122 (10)−0.0023 (10)
O30.0223 (10)0.0183 (9)0.0196 (9)0.0023 (7)0.0085 (8)0.0011 (7)
O40.0370 (14)0.0282 (11)0.0336 (13)0.0027 (10)0.0099 (11)0.0004 (10)
N10.0181 (11)0.0179 (10)0.0231 (12)0.0024 (8)0.0104 (9)0.0018 (9)
N20.0174 (11)0.0175 (10)0.0234 (12)0.0004 (8)0.0106 (9)0.0010 (9)
N30.0164 (11)0.0207 (10)0.0202 (11)−0.0006 (8)0.0081 (9)0.0007 (9)
N40.0183 (11)0.0182 (10)0.0222 (12)−0.0005 (9)0.0089 (9)−0.0016 (9)
C10.0156 (12)0.0204 (12)0.0237 (14)0.0000 (9)0.0113 (11)−0.0038 (10)
C20.0229 (14)0.0213 (12)0.0298 (15)−0.0022 (10)0.0150 (12)−0.0013 (11)
C30.0256 (15)0.0279 (14)0.0383 (17)−0.0078 (12)0.0182 (14)−0.0097 (13)
C40.0183 (14)0.0370 (16)0.0307 (16)−0.0056 (12)0.0077 (12)−0.0071 (13)
C50.0225 (14)0.0328 (15)0.0234 (14)0.0014 (12)0.0089 (12)−0.0002 (12)
C60.0215 (14)0.0246 (13)0.0160 (13)−0.0006 (10)0.0090 (11)−0.0027 (10)
C70.0196 (13)0.0208 (12)0.0220 (13)0.0042 (10)0.0085 (11)0.0014 (10)
C80.0207 (14)0.0212 (13)0.0339 (16)0.0017 (10)0.0109 (12)0.0119 (12)
C90.0249 (14)0.0246 (13)0.0261 (15)−0.0001 (11)0.0130 (12)0.0085 (11)
C100.0190 (13)0.0212 (12)0.0351 (16)0.0028 (10)0.0148 (12)0.0055 (12)
C110.0221 (14)0.0248 (13)0.0327 (16)0.0025 (11)0.0161 (12)0.0069 (12)
C120.0150 (12)0.0186 (12)0.0281 (15)−0.0030 (10)0.0107 (11)−0.0010 (10)
C130.0197 (13)0.0265 (13)0.0237 (14)−0.0016 (11)0.0091 (11)−0.0030 (11)
C140.0236 (14)0.0274 (14)0.0315 (16)−0.0032 (11)0.0144 (13)−0.0087 (12)
C150.0322 (16)0.0198 (13)0.0373 (17)0.0030 (12)0.0160 (14)−0.0022 (12)
C160.0274 (15)0.0204 (13)0.0336 (16)0.0026 (11)0.0149 (13)0.0037 (12)
C170.0196 (13)0.0170 (12)0.0274 (14)−0.0002 (10)0.0134 (11)0.0020 (10)
C180.0182 (12)0.0206 (12)0.0226 (13)0.0001 (10)0.0117 (11)0.0039 (10)
C190.0200 (13)0.0244 (13)0.0163 (13)0.0025 (11)0.0030 (11)0.0005 (11)
C200.0271 (14)0.0256 (13)0.0143 (12)0.0020 (11)0.0090 (11)−0.0017 (11)
C210.0189 (13)0.0301 (14)0.0272 (15)0.0030 (11)0.0092 (12)−0.0047 (12)
C220.0257 (15)0.0317 (15)0.0261 (15)0.0041 (12)0.0128 (13)−0.0033 (12)
Geometric parameters (Å, °) top
Cr1—O11.9207 (19)C7—H7A0.9500
Cr1—O31.929 (2)C8—C91.512 (4)
Cr1—N32.009 (2)C8—H8A0.9900
Cr1—N12.020 (2)C8—H8B0.9900
Cr1—N22.112 (2)C9—H9A0.9900
Cr1—N42.135 (2)C9—H9B0.9900
O1—C11.321 (3)C10—C111.513 (4)
O2—C111.419 (4)C10—H10A0.9900
O2—H2O0.86 (5)C10—H10B0.9900
O3—C121.323 (3)C11—H11A0.9900
O4—C221.417 (4)C11—H11B0.9900
O4—H4O0.78 (4)C12—C131.404 (4)
N1—C71.288 (4)C12—C171.406 (4)
N1—C81.468 (3)C13—C141.380 (4)
N2—C101.485 (3)C13—H13A0.9500
N2—C91.488 (4)C14—C151.394 (5)
N2—H2N0.87 (3)C14—H14A0.9500
N3—C181.292 (3)C15—C161.364 (4)
N3—C191.465 (3)C15—H15A0.9500
N4—C211.497 (4)C16—C171.417 (4)
N4—C201.506 (3)C16—H16A0.9500
N4—H4N0.85 (4)C17—C181.436 (4)
C1—C21.407 (4)C18—H18A0.9500
C1—C61.419 (4)C19—C201.514 (4)
C2—C31.377 (4)C19—H19A0.9900
C2—H2A0.9500C19—H19B0.9900
C3—C41.392 (5)C20—H20A0.9900
C3—H3A0.9500C20—H20B0.9900
C4—C51.370 (4)C21—C221.517 (4)
C4—H4A0.9500C21—H21A0.9900
C5—C61.406 (4)C21—H21B0.9900
C5—H5A0.9500C22—H22A0.9900
C6—C71.439 (4)C22—H22B0.9900
O1—Cr1—O392.51 (9)N2—C9—C8107.9 (2)
O1—Cr1—N393.34 (9)N2—C9—H9A110.1
O3—Cr1—N390.50 (9)C8—C9—H9A110.1
O1—Cr1—N190.29 (9)N2—C9—H9B110.1
O3—Cr1—N192.37 (9)C8—C9—H9B110.1
N3—Cr1—N1175.27 (9)H9A—C9—H9B108.4
O1—Cr1—N2172.00 (9)N2—C10—C11115.2 (2)
O3—Cr1—N286.94 (9)N2—C10—H10A108.5
N3—Cr1—N294.65 (9)C11—C10—H10A108.5
N1—Cr1—N281.76 (9)N2—C10—H10B108.5
O1—Cr1—N488.80 (9)C11—C10—H10B108.5
O3—Cr1—N4172.26 (8)H10A—C10—H10B107.5
N3—Cr1—N481.80 (9)O2—C11—C10113.6 (3)
N1—Cr1—N495.25 (9)O2—C11—H11A108.9
N2—Cr1—N492.81 (9)C10—C11—H11A108.9
C1—O1—Cr1128.43 (18)O2—C11—H11B108.9
C11—O2—H2O109 (3)C10—C11—H11B108.9
C12—O3—Cr1128.60 (18)H11A—C11—H11B107.7
C22—O4—H4O116 (3)O3—C12—C13118.0 (3)
C7—N1—C8119.3 (2)O3—C12—C17124.2 (3)
C7—N1—Cr1126.83 (19)C13—C12—C17117.7 (2)
C8—N1—Cr1113.43 (17)C14—C13—C12121.5 (3)
C10—N2—C9111.8 (2)C14—C13—H13A119.3
C10—N2—Cr1115.81 (16)C12—C13—H13A119.3
C9—N2—Cr1105.84 (17)C13—C14—C15120.7 (3)
C10—N2—H2N109 (2)C13—C14—H14A119.7
C9—N2—H2N104 (2)C15—C14—H14A119.7
Cr1—N2—H2N110 (2)C16—C15—C14119.0 (3)
C18—N3—C19119.7 (2)C16—C15—H15A120.5
C18—N3—Cr1126.3 (2)C14—C15—H15A120.5
C19—N3—Cr1113.92 (17)C15—C16—C17121.4 (3)
C21—N4—C20110.7 (2)C15—C16—H16A119.3
C21—N4—Cr1114.89 (17)C17—C16—H16A119.3
C20—N4—Cr1107.10 (16)C12—C17—C16119.6 (3)
C21—N4—H4N105 (2)C12—C17—C18123.6 (2)
C20—N4—H4N109 (3)C16—C17—C18116.6 (3)
Cr1—N4—H4N110 (3)N3—C18—C17124.8 (3)
O1—C1—C2118.3 (2)N3—C18—H18A117.6
O1—C1—C6124.0 (2)C17—C18—H18A117.6
C2—C1—C6117.7 (3)N3—C19—C20107.9 (2)
C3—C2—C1121.5 (3)N3—C19—H19A110.1
C3—C2—H2A119.3C20—C19—H19A110.1
C1—C2—H2A119.3N3—C19—H19B110.1
C2—C3—C4120.6 (3)C20—C19—H19B110.1
C2—C3—H3A119.7H19A—C19—H19B108.4
C4—C3—H3A119.7N4—C20—C19108.2 (2)
C5—C4—C3119.2 (3)N4—C20—H20A110.1
C5—C4—H4A120.4C19—C20—H20A110.1
C3—C4—H4A120.4N4—C20—H20B110.1
C4—C5—C6121.6 (3)C19—C20—H20B110.1
C4—C5—H5A119.2H20A—C20—H20B108.4
C6—C5—H5A119.2N4—C21—C22114.6 (2)
C5—C6—C1119.4 (3)N4—C21—H21A108.6
C5—C6—C7116.9 (3)C22—C21—H21A108.6
C1—C6—C7123.7 (3)N4—C21—H21B108.6
N1—C7—C6124.3 (3)C22—C21—H21B108.6
N1—C7—H7A117.8H21A—C21—H21B107.6
C6—C7—H7A117.8O4—C22—C21110.6 (3)
N1—C8—C9106.7 (2)O4—C22—H22A109.5
N1—C8—H8A110.4C21—C22—H22A109.5
C9—C8—H8A110.4O4—C22—H22B109.5
N1—C8—H8B110.4C21—C22—H22B109.5
C9—C8—H8B110.4H22A—C22—H22B108.1
H8A—C8—H8B108.6
O3—Cr1—O1—C175.1 (2)C2—C3—C4—C5−0.7 (5)
N3—Cr1—O1—C1165.7 (2)C3—C4—C5—C6−0.3 (5)
N1—Cr1—O1—C1−17.3 (2)C4—C5—C6—C11.0 (4)
N4—Cr1—O1—C1−112.5 (2)C4—C5—C6—C7−179.9 (3)
O1—Cr1—O3—C1281.4 (2)O1—C1—C6—C5178.5 (3)
N3—Cr1—O3—C12−12.0 (2)C2—C1—C6—C5−0.8 (4)
N1—Cr1—O3—C12171.8 (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—C713.2 (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—N1177.5 (3)
N4—Cr1—N1—C7102.1 (2)C1—C6—C7—N1−3.5 (4)
O1—Cr1—N1—C8−174.3 (2)C7—N1—C8—C9139.3 (3)
O3—Cr1—N1—C893.2 (2)Cr1—N1—C8—C9−33.8 (3)
N2—Cr1—N1—C86.7 (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—C1053.9 (2)N1—C8—C9—N253.2 (3)
N3—Cr1—N2—C10−36.3 (2)C9—N2—C10—C11−66.0 (3)
N1—Cr1—N2—C10146.8 (2)Cr1—N2—C10—C11172.7 (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—C174.3 (4)
N1—Cr1—N2—C922.25 (17)O3—C12—C13—C14178.8 (3)
N4—Cr1—N2—C9117.15 (18)C17—C12—C13—C14−2.5 (4)
O1—Cr1—N3—C18−77.8 (2)C12—C13—C14—C150.4 (5)
O3—Cr1—N3—C1814.7 (2)C13—C14—C15—C161.9 (5)
N2—Cr1—N3—C18101.7 (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—C1999.16 (19)C13—C12—C17—C162.3 (4)
O3—Cr1—N3—C19−168.30 (19)O3—C12—C17—C186.4 (4)
N2—Cr1—N3—C19−81.33 (19)C13—C12—C17—C18−172.2 (3)
N4—Cr1—N3—C1910.85 (19)C15—C16—C17—C120.0 (4)
O1—Cr1—N4—C2146.7 (2)C15—C16—C17—C18174.8 (3)
N3—Cr1—N4—C21140.2 (2)C19—N3—C18—C17173.2 (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—C2016.91 (17)C18—N3—C19—C20140.8 (3)
N1—Cr1—N4—C20−166.82 (18)Cr1—N3—C19—C20−36.4 (3)
N2—Cr1—N4—C20111.20 (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—C614.2 (4)N3—C19—C20—N450.4 (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—C22173.0 (2)
C1—C2—C3—C40.9 (5)N4—C21—C22—O4−66.5 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2O···Cl10.86 (5)2.31 (5)3.175 (3)178 (4)
O4—H4O···Cl1i0.78 (4)2.54 (4)3.229 (3)149 (4)
N4—H4N···Cl10.85 (4)2.62 (4)3.457 (3)168 (4)
N2—H2N···Cl10.87 (3)2.30 (3)3.170 (2)177 (3)
Symmetry codes: (i) −x, −y+1, −z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2O···Cl10.86 (5)2.31 (5)3.175 (3)178 (4)
O4—H4O···Cl1i0.78 (4)2.54 (4)3.229 (3)149 (4)
N4—H4N···Cl10.85 (4)2.62 (4)3.457 (3)168 (4)
N2—H2N···Cl10.87 (3)2.30 (3)3.170 (2)177 (3)
Symmetry codes: (i) −x, −y+1, −z.
Acknowledgements top

This work was supported by the Natural Science Foundation of the Education Committee of Guangxi Province, and by the Teaching and Research Award Programme for Outstanding Young Teachers in Higher Education Institutions of the Chinese Ministry of Education. The authors are also grateful to Yulin Normal University for financial support.

references
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