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The title compound, [Cr(C11H15N2O2)2]Cl, is a mononuclear chromium(III) complex with a distorted octa­hedral geometry defined by an N4O2 donor set.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807022118/tk2152sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807022118/tk2152Isup2.hkl
Contains datablock I

CCDC reference: 650615

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.056
  • wR factor = 0.159
  • Data-to-parameter ratio = 14.0

checkCIF/PLATON results

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Alert level C PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cr1 - O1 .. 8.77 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cr1 - O3 .. 8.06 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cr1 - N1 .. 6.94 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cr1 - N2 .. 6.34 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cr1 - N3 .. 5.83 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cr1 - N4 .. 8.52 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Cr1 PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 8
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of N2 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of N4 = ... R PLAT794_ALERT_5_G Check Predicted Bond Valency for Cr1 (9) 4.53
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 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 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 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Bis{N-[2-(2-hydroxyethylamino)ethyl]salicylideneimine}chromium(III) chloride top
Crystal data top
[Cr(C11H15N2O2)2]ClF(000) = 1052
Mr = 501.95Dx = 1.452 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1628 reflections
a = 9.818 (7) Åθ = 3.6–26.2°
b = 24.895 (18) ŵ = 0.65 mm1
c = 10.431 (7) ÅT = 298 K
β = 115.724 (11)°Prism, dark-blue
V = 2297 (3) Å30.37 × 0.25 × 0.13 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer
4052 independent reflections
Radiation source: fine-focus sealed tube2404 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.069
φ and ω scansθmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 911
Tmin = 0.795, Tmax = 0.920k = 2729
12142 measured reflectionsl = 1212
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159H-atom parameters constrained
S = 0.93 w = 1/[σ2(Fo2) + (0.0833P)2]
where P = (Fo2 + 2Fc2)/3
4052 reflections(Δ/σ)max = 0.001
289 parametersΔρmax = 0.69 e Å3
0 restraintsΔρmin = 0.38 e Å3
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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cr10.25210 (7)0.86498 (3)0.13517 (7)0.0302 (2)
Cl10.50308 (18)1.01183 (7)0.30601 (18)0.0911 (6)
N10.3933 (4)0.82192 (16)0.2822 (4)0.0457 (9)
N20.2551 (4)0.91144 (16)0.2953 (4)0.0516 (10)
H20.31720.93970.30420.062*
N30.1135 (4)0.91079 (15)0.0096 (4)0.0481 (10)
N40.4110 (4)0.90866 (15)0.1117 (4)0.0498 (10)
H40.43900.93510.17850.060*
O10.2498 (3)0.82024 (13)0.0119 (3)0.0526 (9)
O20.1913 (5)1.01963 (18)0.3841 (5)0.1013 (14)
H2A0.27641.01240.39290.152*
O30.0969 (3)0.82347 (13)0.1474 (3)0.0524 (9)
O40.7463 (4)0.94778 (18)0.2451 (5)0.0915 (13)
H4A0.68360.96720.25420.137*
C10.4267 (5)0.7730 (2)0.2684 (5)0.0485 (12)
H10.48020.75360.35150.058*
C20.3894 (5)0.74622 (19)0.1388 (5)0.0474 (12)
C30.3107 (5)0.7715 (2)0.0057 (5)0.0489 (12)
C40.2981 (5)0.7433 (2)0.1163 (5)0.0559 (13)
H4B0.24910.75940.20520.067*
C50.3572 (6)0.6924 (2)0.1061 (6)0.0624 (15)
H50.34920.67550.18850.075*
C60.4282 (6)0.6655 (2)0.0229 (6)0.0678 (15)
H60.46280.63050.02780.081*
C70.4448 (6)0.6930 (2)0.1420 (6)0.0617 (14)
H70.49470.67610.22980.074*
C80.4548 (6)0.8475 (2)0.4234 (5)0.0583 (14)
H8A0.53850.87100.43590.070*
H8B0.49020.82060.49800.070*
C90.3280 (6)0.8789 (2)0.4276 (6)0.0681 (16)
H9A0.36570.90230.51000.082*
H9B0.25450.85460.43520.082*
C100.1088 (5)0.9338 (2)0.2808 (6)0.0679 (16)
H10A0.04430.90420.28020.082*
H10B0.06000.95170.18930.082*
C110.1191 (6)0.9727 (2)0.3942 (6)0.0699 (16)
H11A0.01840.98120.38380.084*
H11B0.17520.95660.48710.084*
C120.0285 (6)0.9027 (2)0.0850 (5)0.0500 (12)
H120.08060.92630.15950.060*
C130.1113 (5)0.8596 (2)0.0611 (5)0.0512 (13)
C140.0442 (5)0.82189 (19)0.0506 (5)0.0467 (12)
C150.1380 (6)0.7813 (2)0.0615 (5)0.0567 (14)
H150.09650.75600.13370.068*
C160.2870 (6)0.7777 (2)0.0292 (6)0.0695 (16)
H160.34510.75020.01810.083*
C170.3539 (6)0.8150 (3)0.1395 (6)0.0751 (18)
H170.45590.81250.20180.090*
C180.2654 (6)0.8554 (2)0.1540 (5)0.0663 (16)
H180.30890.88040.22680.080*
C190.1869 (6)0.9559 (2)0.0437 (6)0.0596 (14)
H19A0.20110.98550.02140.072*
H19B0.12600.96830.14000.072*
C200.3375 (6)0.9352 (2)0.0289 (6)0.0644 (15)
H20A0.32320.90980.10420.077*
H20B0.39950.96460.03450.077*
C210.5518 (6)0.8802 (2)0.1299 (6)0.0620 (15)
H21A0.52530.85310.05610.074*
H21B0.59250.86170.22070.074*
C220.6742 (6)0.9151 (2)0.1242 (6)0.0621 (14)
H22A0.74920.89240.11420.074*
H22B0.63040.93790.04060.074*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cr10.0249 (4)0.0285 (4)0.0354 (4)0.0005 (3)0.0114 (3)0.0015 (3)
Cl10.0885 (12)0.0762 (11)0.1075 (13)0.0192 (9)0.0415 (10)0.0300 (10)
N10.043 (2)0.043 (3)0.052 (2)0.0001 (18)0.0207 (19)0.002 (2)
N20.041 (2)0.051 (3)0.056 (3)0.0012 (18)0.016 (2)0.005 (2)
N30.041 (3)0.043 (2)0.059 (3)0.0025 (18)0.021 (2)0.004 (2)
N40.047 (2)0.041 (2)0.060 (3)0.0055 (18)0.023 (2)0.008 (2)
O10.053 (2)0.049 (2)0.053 (2)0.0060 (16)0.0198 (17)0.0023 (16)
O20.101 (3)0.077 (3)0.122 (4)0.008 (3)0.045 (3)0.011 (3)
O30.046 (2)0.050 (2)0.059 (2)0.0044 (15)0.0204 (18)0.0051 (16)
O40.054 (3)0.109 (4)0.103 (3)0.016 (2)0.027 (2)0.022 (3)
C10.047 (3)0.048 (3)0.051 (3)0.001 (2)0.022 (2)0.009 (2)
C20.044 (3)0.044 (3)0.054 (3)0.003 (2)0.021 (2)0.004 (2)
C30.038 (3)0.047 (3)0.064 (3)0.007 (2)0.024 (3)0.004 (3)
C40.054 (3)0.057 (4)0.055 (3)0.002 (3)0.022 (3)0.007 (3)
C50.062 (4)0.060 (4)0.068 (4)0.007 (3)0.030 (3)0.023 (3)
C60.081 (4)0.047 (4)0.077 (4)0.004 (3)0.036 (3)0.001 (3)
C70.071 (4)0.045 (3)0.071 (4)0.002 (3)0.034 (3)0.006 (3)
C80.062 (4)0.057 (4)0.047 (3)0.006 (3)0.016 (3)0.003 (3)
C90.071 (4)0.073 (4)0.056 (3)0.003 (3)0.023 (3)0.007 (3)
C100.045 (3)0.079 (4)0.076 (4)0.006 (3)0.023 (3)0.015 (3)
C110.065 (4)0.075 (4)0.066 (4)0.011 (3)0.025 (3)0.008 (3)
C120.048 (3)0.050 (3)0.049 (3)0.007 (2)0.018 (3)0.000 (2)
C130.040 (3)0.061 (4)0.049 (3)0.000 (2)0.016 (2)0.006 (3)
C140.041 (3)0.050 (3)0.049 (3)0.004 (2)0.020 (2)0.009 (2)
C150.052 (4)0.053 (3)0.069 (3)0.007 (2)0.030 (3)0.005 (3)
C160.056 (4)0.065 (4)0.088 (4)0.017 (3)0.032 (3)0.013 (3)
C170.045 (4)0.094 (5)0.076 (4)0.022 (3)0.016 (3)0.023 (4)
C180.047 (3)0.088 (5)0.057 (3)0.003 (3)0.016 (3)0.006 (3)
C190.054 (3)0.042 (3)0.078 (4)0.001 (2)0.025 (3)0.014 (3)
C200.050 (3)0.065 (4)0.078 (4)0.000 (3)0.027 (3)0.025 (3)
C210.050 (3)0.054 (4)0.089 (4)0.003 (2)0.036 (3)0.008 (3)
C220.047 (3)0.061 (4)0.084 (4)0.004 (3)0.035 (3)0.007 (3)
Geometric parameters (Å, º) top
Cr1—O11.888 (3)C7—H70.9300
Cr1—O31.891 (3)C8—C91.486 (7)
Cr1—N11.891 (4)C8—H8A0.9700
Cr1—N31.910 (4)C8—H8B0.9700
Cr1—N42.002 (4)C9—H9A0.9700
Cr1—N22.022 (4)C9—H9B0.9700
N1—C11.285 (6)C10—C111.498 (7)
N1—C81.473 (6)C10—H10A0.9700
N2—C101.485 (6)C10—H10B0.9700
N2—C91.489 (6)C11—H11A0.9700
N2—H20.9100C11—H11B0.9700
N3—C121.285 (5)C12—C131.432 (7)
N3—C191.460 (6)C12—H120.9300
N4—C201.480 (6)C13—C181.402 (6)
N4—C211.491 (6)C13—C141.416 (6)
N4—H40.9100C14—C151.404 (6)
O1—C31.330 (6)C15—C161.357 (7)
O2—C111.394 (7)C15—H150.9300
O2—H2A0.8200C16—C171.399 (8)
O3—C141.314 (5)C16—H160.9300
O4—C221.406 (6)C17—C181.380 (7)
O4—H4A0.8200C17—H170.9300
C1—C21.406 (6)C18—H180.9300
C1—H10.9300C19—C201.510 (7)
C2—C31.410 (6)C19—H19A0.9700
C2—C71.428 (7)C19—H19B0.9700
C3—C41.410 (6)C20—H20A0.9700
C4—C51.379 (7)C20—H20B0.9700
C4—H4B0.9300C21—C221.505 (7)
C5—C61.389 (7)C21—H21A0.9700
C5—H50.9300C21—H21B0.9700
C6—C71.365 (7)C22—H22A0.9700
C6—H60.9300C22—H22B0.9700
O1—Cr1—O390.37 (14)C8—C9—N2109.3 (4)
O1—Cr1—N194.02 (16)C8—C9—H9A109.8
O3—Cr1—N187.95 (15)N2—C9—H9A109.8
O1—Cr1—N387.52 (16)C8—C9—H9B109.8
O3—Cr1—N393.51 (16)N2—C9—H9B109.8
N1—Cr1—N3177.87 (17)H9A—C9—H9B108.3
O1—Cr1—N487.49 (15)N2—C10—C11115.5 (4)
O3—Cr1—N4177.15 (15)N2—C10—H10A108.4
N1—Cr1—N494.07 (16)C11—C10—H10A108.4
N3—Cr1—N484.52 (16)N2—C10—H10B108.4
O1—Cr1—N2178.72 (15)C11—C10—H10B108.4
O3—Cr1—N288.85 (15)H10A—C10—H10B107.5
N1—Cr1—N284.94 (17)O2—C11—C10110.1 (5)
N3—Cr1—N293.54 (16)O2—C11—H11A109.6
N4—Cr1—N293.32 (16)C10—C11—H11A109.6
C1—N1—C8120.6 (4)O2—C11—H11B109.6
C1—N1—Cr1125.4 (3)C10—C11—H11B109.6
C8—N1—Cr1113.8 (3)H11A—C11—H11B108.2
C10—N2—C9110.7 (4)N3—C12—C13123.9 (4)
C10—N2—Cr1117.6 (3)N3—C12—H12118.0
C9—N2—Cr1106.4 (3)C13—C12—H12118.0
C10—N2—H2107.2C18—C13—C14119.8 (5)
C9—N2—H2107.2C18—C13—C12117.3 (5)
Cr1—N2—H2107.2C14—C13—C12122.9 (4)
C12—N3—C19119.4 (4)O3—C14—C15118.0 (4)
C12—N3—Cr1127.0 (3)O3—C14—C13124.8 (4)
C19—N3—Cr1113.3 (3)C15—C14—C13117.1 (5)
C20—N4—C21111.4 (4)C16—C15—C14122.5 (5)
C20—N4—Cr1107.1 (3)C16—C15—H15118.7
C21—N4—Cr1117.1 (3)C14—C15—H15118.7
C20—N4—H4106.9C15—C16—C17120.6 (5)
C21—N4—H4106.9C15—C16—H16119.7
Cr1—N4—H4106.9C17—C16—H16119.7
C3—O1—Cr1125.5 (3)C18—C17—C16118.7 (5)
C11—O2—H2A109.5C18—C17—H17120.6
C14—O3—Cr1125.2 (3)C16—C17—H17120.6
C22—O4—H4A109.5C17—C18—C13121.3 (5)
N1—C1—C2125.8 (5)C17—C18—H18119.3
N1—C1—H1117.1C13—C18—H18119.3
C2—C1—H1117.1N3—C19—C20106.1 (4)
C1—C2—C3122.5 (4)N3—C19—H19A110.5
C1—C2—C7118.7 (5)C20—C19—H19A110.5
C3—C2—C7118.5 (5)N3—C19—H19B110.5
O1—C3—C2124.3 (4)C20—C19—H19B110.5
O1—C3—C4118.1 (4)H19A—C19—H19B108.7
C2—C3—C4117.6 (5)N4—C20—C19106.7 (4)
C5—C4—C3121.2 (5)N4—C20—H20A110.4
C5—C4—H4B119.4C19—C20—H20A110.4
C3—C4—H4B119.4N4—C20—H20B110.4
C4—C5—C6122.4 (5)C19—C20—H20B110.4
C4—C5—H5118.8H20A—C20—H20B108.6
C6—C5—H5118.8N4—C21—C22115.6 (4)
C7—C6—C5116.9 (5)N4—C21—H21A108.4
C7—C6—H6121.6C22—C21—H21A108.4
C5—C6—H6121.6N4—C21—H21B108.4
C6—C7—C2123.4 (5)C22—C21—H21B108.4
C6—C7—H7118.3H21A—C21—H21B107.4
C2—C7—H7118.3O4—C22—C21113.5 (4)
N1—C8—C9105.8 (4)O4—C22—H22A108.9
N1—C8—H8A110.6C21—C22—H22A108.9
C9—C8—H8A110.6O4—C22—H22B108.9
N1—C8—H8B110.6C21—C22—H22B108.9
C9—C8—H8B110.6H22A—C22—H22B107.7
H8A—C8—H8B108.7
O1—Cr1—N1—C117.2 (4)Cr1—O1—C3—C4179.7 (3)
O3—Cr1—N1—C173.0 (4)C1—C2—C3—O17.8 (7)
N4—Cr1—N1—C1104.9 (4)C7—C2—C3—O1177.9 (4)
N2—Cr1—N1—C1162.1 (4)C1—C2—C3—C4171.2 (4)
O1—Cr1—N1—C8168.6 (3)C7—C2—C3—C43.1 (7)
O3—Cr1—N1—C8101.1 (3)O1—C3—C4—C5179.3 (4)
N4—Cr1—N1—C880.9 (3)C2—C3—C4—C51.7 (7)
N2—Cr1—N1—C812.1 (3)C3—C4—C5—C61.7 (8)
O3—Cr1—N2—C1051.6 (4)C4—C5—C6—C73.5 (8)
N1—Cr1—N2—C10139.6 (4)C5—C6—C7—C21.9 (8)
N3—Cr1—N2—C1041.8 (4)C1—C2—C7—C6173.2 (5)
N4—Cr1—N2—C10126.6 (4)C3—C2—C7—C61.4 (7)
O3—Cr1—N2—C973.2 (3)C1—N1—C8—C9138.4 (5)
N1—Cr1—N2—C914.8 (3)Cr1—N1—C8—C936.1 (5)
N3—Cr1—N2—C9166.7 (3)N1—C8—C9—N248.3 (6)
N4—Cr1—N2—C9108.6 (3)C10—N2—C9—C8167.6 (4)
O1—Cr1—N3—C1276.2 (4)Cr1—N2—C9—C838.7 (5)
O3—Cr1—N3—C1214.0 (4)C9—N2—C10—C1163.8 (6)
N4—Cr1—N3—C12163.9 (4)Cr1—N2—C10—C11173.6 (4)
N2—Cr1—N3—C12103.1 (4)N2—C10—C11—O267.3 (6)
O1—Cr1—N3—C1996.7 (3)C19—N3—C12—C13179.7 (4)
O3—Cr1—N3—C19173.1 (3)Cr1—N3—C12—C137.3 (7)
N4—Cr1—N3—C199.0 (3)N3—C12—C13—C18178.9 (5)
N2—Cr1—N3—C1984.1 (3)N3—C12—C13—C141.1 (7)
O1—Cr1—N4—C2068.0 (3)Cr1—O3—C14—C15167.4 (3)
N1—Cr1—N4—C20161.9 (3)Cr1—O3—C14—C1315.5 (6)
N3—Cr1—N4—C2019.7 (3)C18—C13—C14—O3176.7 (4)
N2—Cr1—N4—C20113.0 (3)C12—C13—C14—O33.3 (7)
O1—Cr1—N4—C2157.8 (4)C18—C13—C14—C150.4 (7)
N1—Cr1—N4—C2136.1 (4)C12—C13—C14—C15179.6 (4)
N3—Cr1—N4—C21145.5 (4)O3—C14—C15—C16177.0 (5)
N2—Cr1—N4—C21121.2 (4)C13—C14—C15—C160.3 (7)
O3—Cr1—O1—C376.9 (4)C14—C15—C16—C170.1 (8)
N1—Cr1—O1—C311.1 (4)C15—C16—C17—C180.0 (8)
N3—Cr1—O1—C3170.4 (4)C16—C17—C18—C130.1 (8)
N4—Cr1—O1—C3105.0 (4)C14—C13—C18—C170.3 (8)
O1—Cr1—O3—C1469.8 (4)C12—C13—C18—C17179.7 (5)
N1—Cr1—O3—C14163.8 (4)C12—N3—C19—C20138.6 (4)
N3—Cr1—O3—C1417.7 (4)Cr1—N3—C19—C2034.9 (5)
N2—Cr1—O3—C14111.2 (4)C21—N4—C20—C19172.3 (4)
C8—N1—C1—C2172.4 (4)Cr1—N4—C20—C1943.2 (5)
Cr1—N1—C1—C213.8 (7)N3—C19—C20—N450.5 (5)
N1—C1—C2—C31.1 (7)C20—N4—C21—C2261.5 (6)
N1—C1—C2—C7175.4 (4)Cr1—N4—C21—C22174.9 (4)
Cr1—O1—C3—C21.3 (6)N4—C21—C22—O472.1 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···Cl10.912.553.457 (5)172
N4—H4···Cl10.912.263.152 (4)168
O2—H2A···Cl10.822.743.498 (5)154
O4—H4A···Cl10.822.353.157 (5)170
 

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