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The title compound, [In(C2H5)(C14H13N2)2], contains an InIII atom in a square-pyramidal geometry. The phenyl rings are almost coplanar in one of the amidinate ligands but significantly twisted with respect to each other in the other ligand.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804002867/tk6150sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804002867/tk6150Isup2.hkl
Contains datablock I

CCDC reference: 236031

Key indicators

  • Single-crystal X-ray study
  • T = 240 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.048
  • wR factor = 0.124
  • Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 24.10 Deg. PLAT761_ALERT_1_A CIF Contains no X-H Bonds ...................... ?
Alert level B THETM01_ALERT_3_B The value of sine(theta_max)/wavelength is less than 0.575 Calculated sin(theta_max)/wavelength = 0.5745
Alert level C PLAT023_ALERT_3_C Resolution (too) Low [sin(th)/Lambda < 0.6]..... 24.10 Deg. PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
2 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 4 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: Siemens P3R3 software; cell refinement: Siemens P3R3 software; data reduction: SHELXTL-Plus (Sheldrick, 1994); program(s) used to solve structure: SHELXS90 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldick, 1994); software used to prepare material for publication: SHELXL97.

(I) top
Crystal data top
[In(C2H5)(C14H13N2)2]Z = 2
Mr = 562.41F(000) = 576
Triclinic, P1Dx = 1.392 Mg m3
a = 10.056 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.014 (7) ÅCell parameters from 18 reflections
c = 12.842 (8) Åθ = 10–11°
α = 107.11 (5)°µ = 0.91 mm1
β = 94.83 (5)°T = 240 K
γ = 111.92 (4)°Block, colourless
V = 1342.3 (15) Å30.37 × 0.35 × 0.27 mm
Data collection top
Siemens P3/R3
diffractometer
Rint = 0.076
ω–2θ scansθmax = 24.1°, θmin = 2.1°
Absorption correction: gaussian
(Alcock, 1970)
h = 011
Tmin = 0.731, Tmax = 0.792k = 1312
4504 measured reflectionsl = 1414
4232 independent reflections3 standard reflections every 200 reflections
3640 reflections with I > 2σ(I) intensity decay: 6%
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.048 w = 1/[σ2(Fo2) + (0.0878P)2 + 0.2286P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.124(Δ/σ)max < 0.001
S = 1.05Δρmax = 1.15 e Å3
4232 reflectionsΔρmin = 1.23 e Å3
319 parameters
Special details top

Experimental. The temperature of the crystal was controlled using the Oxford Cryosystem Cryostream Cooler (Cosier & Glazer, 1986). Due to the fact that the crystals were unstable and did not diffract strongly at high angles, the data were only collected to θmax of 24.1°

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
In10.12291 (4)0.15701 (3)0.33165 (3)0.03694 (15)
N10.1313 (5)0.0015 (4)0.1834 (3)0.0417 (10)
N20.3051 (4)0.1979 (4)0.2382 (3)0.0404 (9)
N30.0604 (5)0.3194 (4)0.3226 (4)0.0417 (9)
N40.1098 (5)0.1197 (4)0.2709 (4)0.0418 (10)
C10.0576 (5)0.1319 (5)0.1198 (4)0.0407 (11)
C20.0503 (6)0.2185 (5)0.1722 (5)0.0517 (13)
H20.09920.18870.24720.062*
C30.0285 (8)0.3491 (6)0.1153 (6)0.0664 (17)
H30.03210.40740.15150.08*
C40.1017 (7)0.3935 (6)0.0052 (6)0.0678 (18)
H40.15570.48190.03350.081*
C50.0950 (7)0.3073 (6)0.0474 (5)0.0625 (16)
H50.14550.33710.1220.075*
C60.0140 (6)0.1765 (5)0.0092 (5)0.0516 (13)
H60.00790.11830.02770.062*
C70.2542 (5)0.0804 (5)0.1657 (4)0.0384 (11)
C80.3277 (6)0.0363 (5)0.0746 (5)0.0483 (13)
H8A0.28620.04140.0060.072*
H8B0.3120.05160.06270.072*
H8C0.43230.09080.09620.072*
C90.4351 (5)0.3033 (5)0.2430 (4)0.0410 (11)
C100.4667 (6)0.3394 (5)0.1516 (5)0.0497 (13)
H100.40460.2890.08060.06*
C110.5897 (7)0.4498 (6)0.1647 (5)0.0578 (15)
H110.61190.47230.1020.069*
C120.6793 (6)0.5264 (5)0.2681 (6)0.0572 (15)
H120.76060.60230.27640.069*
C130.6495 (6)0.4917 (5)0.3604 (5)0.0526 (14)
H130.7110.54350.43130.063*
C140.5287 (6)0.3804 (5)0.3474 (4)0.0438 (12)
H140.50940.35640.40980.053*
C150.2522 (6)0.0191 (5)0.2433 (4)0.0412 (11)
C160.2677 (7)0.1050 (5)0.1908 (5)0.0526 (14)
H160.18610.11950.17130.063*
C170.4043 (8)0.2089 (6)0.1666 (5)0.0630 (16)
H170.41380.2930.13180.076*
C180.5247 (7)0.1882 (7)0.1939 (5)0.0670 (18)
H180.61690.25780.17550.08*
C190.5100 (7)0.0663 (7)0.2478 (6)0.0641 (16)
H190.59220.05250.26710.077*
C200.3743 (6)0.0372 (6)0.2742 (5)0.0504 (13)
H200.36470.12030.31320.061*
C210.0809 (6)0.2392 (5)0.2766 (4)0.0428 (12)
C220.1887 (6)0.2766 (6)0.2218 (5)0.0528 (14)
H22A0.13620.34270.19290.079*
H22B0.23880.30890.27640.079*
H22C0.26020.20210.1610.079*
C230.1225 (6)0.4534 (4)0.3489 (4)0.0402 (11)
C240.2687 (6)0.5140 (5)0.3427 (4)0.0474 (12)
H240.31990.4640.31590.057*
C250.3398 (6)0.6456 (5)0.3751 (5)0.0525 (13)
H250.4380.6840.36960.063*
C260.2668 (7)0.7215 (5)0.4157 (5)0.0568 (15)
H260.31560.81130.43950.068*
C270.1224 (8)0.6636 (6)0.4206 (5)0.0610 (16)
H270.07180.71470.44590.073*
C280.0485 (7)0.5299 (5)0.3886 (5)0.0503 (13)
H280.04990.4920.39390.06*
C290.1903 (7)0.1478 (6)0.4917 (4)0.0538 (14)
H29A0.25630.23430.54260.065*
H29B0.10350.11780.52280.065*
C300.2663 (10)0.0614 (8)0.4864 (6)0.087 (2)
H30A0.19650.02690.44750.13*
H30B0.30730.07170.56160.13*
H30C0.34470.08320.44680.13*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
In10.0373 (2)0.0339 (2)0.0448 (2)0.01784 (15)0.00913 (15)0.01713 (15)
N10.041 (2)0.041 (2)0.044 (2)0.018 (2)0.0085 (19)0.0137 (19)
N20.040 (2)0.032 (2)0.046 (2)0.0146 (18)0.0126 (19)0.0108 (18)
N30.042 (2)0.035 (2)0.055 (2)0.0193 (19)0.014 (2)0.0197 (19)
N40.039 (2)0.036 (2)0.053 (2)0.0178 (19)0.0094 (19)0.0168 (19)
C10.036 (3)0.040 (3)0.047 (3)0.019 (2)0.011 (2)0.013 (2)
C20.052 (3)0.045 (3)0.056 (3)0.017 (3)0.009 (3)0.018 (3)
C30.079 (5)0.039 (3)0.083 (5)0.020 (3)0.028 (4)0.027 (3)
C40.057 (4)0.039 (3)0.079 (5)0.004 (3)0.020 (3)0.001 (3)
C50.053 (4)0.062 (4)0.054 (3)0.019 (3)0.007 (3)0.004 (3)
C60.052 (3)0.053 (3)0.052 (3)0.024 (3)0.010 (3)0.018 (3)
C70.035 (3)0.043 (3)0.045 (3)0.022 (2)0.003 (2)0.021 (2)
C80.050 (3)0.049 (3)0.054 (3)0.028 (3)0.019 (3)0.016 (2)
C90.034 (3)0.039 (3)0.053 (3)0.021 (2)0.012 (2)0.014 (2)
C100.053 (3)0.050 (3)0.048 (3)0.022 (3)0.009 (2)0.020 (2)
C110.067 (4)0.051 (3)0.070 (4)0.030 (3)0.026 (3)0.032 (3)
C120.045 (3)0.037 (3)0.085 (4)0.014 (3)0.019 (3)0.019 (3)
C130.042 (3)0.046 (3)0.063 (3)0.021 (3)0.006 (3)0.008 (3)
C140.045 (3)0.038 (3)0.052 (3)0.022 (2)0.012 (2)0.013 (2)
C150.040 (3)0.047 (3)0.044 (3)0.023 (2)0.008 (2)0.019 (2)
C160.052 (3)0.049 (3)0.063 (3)0.022 (3)0.020 (3)0.025 (3)
C170.074 (4)0.044 (3)0.065 (4)0.017 (3)0.015 (3)0.021 (3)
C180.048 (4)0.068 (4)0.072 (4)0.003 (3)0.001 (3)0.037 (3)
C190.045 (3)0.084 (5)0.075 (4)0.029 (3)0.017 (3)0.041 (4)
C200.048 (3)0.055 (3)0.057 (3)0.026 (3)0.016 (3)0.026 (3)
C210.044 (3)0.051 (3)0.050 (3)0.031 (3)0.017 (2)0.022 (2)
C220.049 (3)0.061 (3)0.063 (3)0.033 (3)0.009 (3)0.029 (3)
C230.048 (3)0.036 (3)0.045 (3)0.022 (2)0.011 (2)0.020 (2)
C240.044 (3)0.047 (3)0.055 (3)0.023 (2)0.009 (2)0.019 (2)
C250.045 (3)0.047 (3)0.060 (3)0.013 (3)0.006 (3)0.022 (3)
C260.064 (4)0.043 (3)0.063 (4)0.021 (3)0.004 (3)0.021 (3)
C270.080 (5)0.054 (3)0.064 (4)0.044 (3)0.017 (3)0.019 (3)
C280.054 (3)0.054 (3)0.056 (3)0.031 (3)0.020 (3)0.025 (3)
C290.067 (4)0.059 (3)0.038 (3)0.029 (3)0.009 (3)0.018 (3)
C300.128 (7)0.093 (5)0.062 (4)0.074 (5)0.002 (4)0.029 (4)
Geometric parameters (Å, º) top
In1—C292.157 (5)C13—C141.383 (8)
In1—N42.234 (4)C13—H130.94
In1—N22.255 (4)C14—H140.94
In1—N12.274 (4)C15—C161.385 (8)
In1—N32.292 (4)C15—C201.393 (7)
N1—C71.333 (6)C16—C171.401 (9)
N1—C11.424 (6)C16—H160.94
N2—C71.315 (6)C17—C181.377 (9)
N2—C91.422 (6)C17—H170.94
N3—C211.341 (7)C18—C191.368 (10)
N3—C231.411 (6)C18—H180.94
N4—C211.331 (6)C19—C201.390 (8)
N4—C151.417 (7)C19—H190.94
C1—C21.380 (7)C20—H200.94
C1—C61.384 (8)C21—C221.515 (7)
C2—C31.387 (8)C22—H22A0.97
C2—H20.94C22—H22B0.97
C3—C41.383 (10)C22—H22C0.97
C3—H30.94C23—C241.397 (7)
C4—C51.379 (10)C23—C281.399 (7)
C4—H40.94C24—C251.379 (8)
C5—C61.390 (8)C24—H240.94
C5—H50.94C25—C261.388 (8)
C6—H60.94C25—H250.94
C7—C81.507 (7)C26—C271.373 (9)
C8—H8A0.97C26—H260.94
C8—H8B0.97C27—C281.404 (8)
C8—H8C0.97C27—H270.94
C9—C101.388 (7)C28—H280.94
C9—C141.395 (7)C29—C301.492 (9)
C10—C111.388 (8)C29—H29A0.98
C10—H100.94C29—H29B0.98
C11—C121.371 (9)C30—H30A0.97
C11—H110.94C30—H30B0.97
C12—C131.388 (9)C30—H30C0.97
C12—H120.94
C29—In1—N4120.3 (2)C14—C13—H13120.2
C29—In1—N2113.2 (2)C12—C13—H13120.2
N4—In1—N2126.51 (16)C13—C14—C9120.9 (5)
C29—In1—N1114.18 (19)C13—C14—H14119.5
N4—In1—N196.12 (16)C9—C14—H14119.5
N2—In1—N158.22 (15)C16—C15—C20118.3 (5)
C29—In1—N3119.96 (19)C16—C15—N4117.8 (5)
N4—In1—N358.75 (15)C20—C15—N4123.6 (5)
N2—In1—N396.83 (15)C15—C16—C17120.4 (6)
N1—In1—N3125.80 (15)C15—C16—H16119.8
C7—N1—C1123.8 (4)C17—C16—H16119.8
C7—N1—In193.9 (3)C18—C17—C16120.1 (6)
C1—N1—In1142.3 (3)C18—C17—H17120
C7—N2—C9126.3 (4)C16—C17—H17120
C7—N2—In195.3 (3)C19—C18—C17120.0 (6)
C9—N2—In1138.4 (3)C19—C18—H18120
C21—N3—C23126.0 (4)C17—C18—H18120
C21—N3—In192.8 (3)C18—C19—C20120.3 (6)
C23—N3—In1141.1 (3)C18—C19—H19119.9
C21—N4—C15125.1 (4)C20—C19—H19119.9
C21—N4—In195.7 (3)C19—C20—C15120.8 (6)
C15—N4—In1138.9 (3)C19—C20—H20119.6
C2—C1—C6119.4 (5)C15—C20—H20119.6
C2—C1—N1118.7 (5)N4—C21—N3112.4 (4)
C6—C1—N1121.8 (5)N4—C21—C22123.8 (5)
C1—C2—C3120.6 (6)N3—C21—C22123.2 (5)
C1—C2—H2119.7C21—C22—H22A109.5
C3—C2—H2119.7C21—C22—H22B109.5
C4—C3—C2120.0 (6)H22A—C22—H22B109.5
C4—C3—H3120C21—C22—H22C109.5
C2—C3—H3120H22A—C22—H22C109.5
C5—C4—C3119.6 (6)H22B—C22—H22C109.5
C5—C4—H4120.2C24—C23—C28118.2 (5)
C3—C4—H4120.2C24—C23—N3118.4 (4)
C4—C5—C6120.4 (6)C28—C23—N3123.2 (5)
C4—C5—H5119.8C25—C24—C23121.5 (5)
C6—C5—H5119.8C25—C24—H24119.2
C1—C6—C5120.0 (6)C23—C24—H24119.2
C1—C6—H6120C24—C25—C26120.2 (6)
C5—C6—H6120C24—C25—H25119.9
N2—C7—N1112.6 (4)C26—C25—H25119.9
N2—C7—C8124.6 (5)C27—C26—C25119.1 (5)
N1—C7—C8122.8 (5)C27—C26—H26120.5
C7—C8—H8A109.5C25—C26—H26120.5
C7—C8—H8B109.5C26—C27—C28121.5 (6)
H8A—C8—H8B109.5C26—C27—H27119.3
C7—C8—H8C109.5C28—C27—H27119.3
H8A—C8—H8C109.5C23—C28—C27119.5 (5)
H8B—C8—H8C109.5C23—C28—H28120.3
C10—C9—C14118.7 (5)C27—C28—H28120.3
C10—C9—N2123.4 (5)C30—C29—In1113.6 (4)
C14—C9—N2117.7 (5)C30—C29—H29A108.9
C11—C10—C9120.1 (5)In1—C29—H29A108.9
C11—C10—H10119.9C30—C29—H29B108.9
C9—C10—H10119.9In1—C29—H29B108.9
C12—C11—C10120.8 (6)H29A—C29—H29B107.7
C12—C11—H11119.6C29—C30—H30A109.5
C10—C11—H11119.6C29—C30—H30B109.5
C11—C12—C13119.9 (5)H30A—C30—H30B109.5
C11—C12—H12120.1C29—C30—H30C109.5
C13—C12—H12120.1H30A—C30—H30C109.5
C14—C13—C12119.6 (5)H30B—C30—H30C109.5
C29—In1—N1—C7103.9 (3)C1—N1—C7—C80.7 (7)
N4—In1—N1—C7129.0 (3)In1—N1—C7—C8178.9 (4)
N2—In1—N1—C70.6 (3)C7—N2—C9—C1051.3 (7)
N3—In1—N1—C773.5 (3)In1—N2—C9—C10129.2 (5)
C29—In1—N1—C173.6 (6)C7—N2—C9—C14134.6 (5)
N4—In1—N1—C153.5 (5)In1—N2—C9—C1445.0 (7)
N2—In1—N1—C1176.9 (6)C14—C9—C10—C110.4 (8)
N3—In1—N1—C1109.1 (5)N2—C9—C10—C11174.5 (5)
C29—In1—N2—C7105.6 (3)C9—C10—C11—C121.9 (9)
N4—In1—N2—C771.8 (3)C10—C11—C12—C131.9 (9)
N1—In1—N2—C70.6 (3)C11—C12—C13—C140.6 (8)
N3—In1—N2—C7127.6 (3)C12—C13—C14—C90.8 (8)
C29—In1—N2—C974.0 (5)C10—C9—C14—C130.9 (7)
N4—In1—N2—C9108.6 (5)N2—C9—C14—C13173.6 (4)
N1—In1—N2—C9179.0 (6)C21—N4—C15—C16150.4 (5)
N3—In1—N2—C952.7 (5)In1—N4—C15—C1637.3 (7)
C29—In1—N3—C21112.9 (3)C21—N4—C15—C2035.1 (8)
N4—In1—N3—C213.5 (3)In1—N4—C15—C20137.3 (5)
N2—In1—N3—C21125.4 (3)C20—C15—C16—C171.9 (8)
N1—In1—N3—C2170.0 (3)N4—C15—C16—C17176.7 (5)
C29—In1—N3—C2366.9 (6)C15—C16—C17—C180.7 (9)
N4—In1—N3—C23176.2 (6)C16—C17—C18—C192.0 (10)
N2—In1—N3—C2354.8 (5)C17—C18—C19—C200.7 (10)
N1—In1—N3—C23110.3 (5)C18—C19—C20—C152.0 (9)
C29—In1—N4—C21112.4 (3)C16—C15—C20—C193.2 (8)
N2—In1—N4—C2170.4 (3)N4—C15—C20—C19177.8 (5)
N1—In1—N4—C21125.0 (3)C15—N4—C21—N3169.3 (4)
N3—In1—N4—C213.6 (3)In1—N4—C21—N35.7 (5)
C29—In1—N4—C1561.4 (5)C15—N4—C21—C2219.4 (8)
N2—In1—N4—C15115.9 (5)In1—N4—C21—C22165.6 (4)
N1—In1—N4—C1561.3 (5)C23—N3—C21—N4174.3 (4)
N3—In1—N4—C15170.1 (6)In1—N3—C21—N45.5 (4)
C7—N1—C1—C2114.7 (6)C23—N3—C21—C2214.3 (8)
In1—N1—C1—C262.2 (7)In1—N3—C21—C22165.9 (5)
C7—N1—C1—C669.2 (7)C21—N3—C23—C24148.5 (5)
In1—N1—C1—C6113.8 (6)In1—N3—C23—C2431.8 (8)
C6—C1—C2—C30.3 (9)C21—N3—C23—C2836.4 (8)
N1—C1—C2—C3175.8 (5)In1—N3—C23—C28143.4 (5)
C1—C2—C3—C40.6 (10)C28—C23—C24—C250.3 (8)
C2—C3—C4—C50.4 (10)N3—C23—C24—C25175.1 (5)
C3—C4—C5—C60.6 (10)C23—C24—C25—C260.5 (9)
C2—C1—C6—C51.4 (8)C24—C25—C26—C271.5 (9)
N1—C1—C6—C5174.6 (5)C25—C26—C27—C281.9 (9)
C4—C5—C6—C11.6 (9)C24—C23—C28—C270.1 (8)
C9—N2—C7—N1178.7 (4)N3—C23—C28—C27175.3 (5)
In1—N2—C7—N11.0 (4)C26—C27—C28—C231.2 (9)
C9—N2—C7—C80.9 (8)N4—In1—C29—C30127.0 (5)
In1—N2—C7—C8178.8 (4)N2—In1—C29—C3050.6 (6)
C1—N1—C7—N2177.2 (4)N1—In1—C29—C3013.6 (6)
In1—N1—C7—N21.0 (4)N3—In1—C29—C30163.9 (5)
 

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